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 | STRUCTURAL CHEMISTRY |
ISSN: 2053-2296
accessThe influence of the axial group on the crystal structures of boron subphthalocyanines
aDepartment of Chemical Engineering and Applied Chemistry, University of Toronto, 200 College Street, Toronto, Ontario, M5S 3E5, Canada, bDepartment of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada, cDepartment of Materials Science and Engineering, University of Toronto, 184 College Street, Toronto, Ontario, M5S 3E4, Canada, and dDepartment of Mechanical & Industrial Engineering, University of Toronto, 5 King's College Road, Toronto, Ontario, M5S 3G8, Canada
*Correspondence e-mail: tim.bender@utoronto.ca
Edited by R. Diniz, Universidade Federal de Minas Gerais, Brazil (Received 21 June 2024; accepted 15 July 2024; online 4 September 2024)
The crystal structures of 16 boron subphthalocyanines (BsubPcs) with structurally diverse axial groups were analyzed and compared to elucidate the impact of the axial group on the intermolecular π–π interactions, axial-group interactions, axial bond length and BsubPc bowl depth. π–π interactions between the isoindole units of adjacent BsubPc molecules most often involve concave–concave packing, whereas axial-group interactions with adjacent BsubPc molecules tend to favour the convex side of the BsubPc bowl. Furthermore, axial groups that contain O and/or F atoms tend to have significant hydrogen-bonding interactions, while axial groups containing arene site(s) can participate in π–π interactions with the BsubPc bowl, both of which can strongly influence the crystal packing. Bulky axial groups did tend to disrupt the π–π interactions and/or axial-group interactions, preventing some of the close packing that is seen in BsubPcs with less bulky axial groups. The atomic radius of the heteroatom bonded to boron directly influences the axial bond length, whereas the axial group has minimal impact on the BsubPc bowl depth. Finally, the crystal growth method did not generally appear to have a significant impact on the solid-state arrangement, with the exception of water occasionally being incorporated into crystal structures when hygroscopic solvents were used. These insights can help with the design and fine-tuning of the solid-state structures of BsubPcs as they continue to be developed as functional materials in organic electronics.
Keywords: crystal structure; subphthalocyanine; boron; axial; crystal growth; solid state; sublimation; slow vapour diffusion; slow evaporation; organic electronics.
1. Introduction
Boron subphthalocyanines (BsubPcs) are a class of nonplanar aromatic organic compounds with a unique bowl-shaped structure. The BsubPcs are homologues of the phthalocyanine (Pc) family and are comprised of three diiminoisoindole units templated around a boron centre (Fig. 1![[link]](../../../../../../logos/arrows/c_arr.gif){kind=small}
) (Claessens et al., 2014). An additional substituent bonded to boron protrudes from the convex side of the bowl and is known as the axial group (Farac et al., 2023; Zigelstein & Bender, 2024). BsubPcs were first synthesized accidentally by Meller and Ossko in 1972 when trying to incorporate boron as the central atom in a phthalocyanine (Pc) (Grant et al., 2019; Meller & Ossko, 1972). Instead of the anticipated planar macrocycle with four repeating diiminoisoindole units that is a part of the Pc structure, they discovered Cl-BsubPc as a purple nonplanar compound with three diiminoisoindole units around the boron centre, with chlorine in the axial position [Fig. 1(c)] (Grant et al., 2019). The characteristic nonplanar shape of BsubPcs is caused by the atomic radius of boron being slightly larger than the cavity it occupies (Morse & Bender, 2012a). Numerous BsubPc derivatives have been synthesized in the ∼50 years since their discovery, with many physical properties, including the solid-state arrangement, being influenced by substitution at the axial and/or peripheral positions of the BsubPc macrocycle (Morse et al., 2014). The unique optical, electronic and physical properties of BsubPcs, as well as the ability to tune these properties through axial and/or peripheral derivatization, have led to the development of these materials for organic electronic applications, such as organic photovoltaics (OPVs) (Grant et al., 2019; Mutolo et al., 2006), organic light-emitting diodes (OLEDs) (Morse & Bender, 2012a: Morse et al., 2010) and organic thin film transistors (OTFTs) (Yasuda & Tsutsui, 2006).
![[Figure 1]](dg3059fig1thm.gif){kind=small} | Figure 1 (a) General 2D structure of the BsubPc unit with key terms labelled, including the peripheral substituents (Rp), imine (Nimine) and pyrrole (Npyr) N atoms, and different π units (πPh in red and πpyr in green). (b) General 2D structure of the BsubPc unit with `head' (orange highlight) and `tail' (purple highlight) labelled. (c) General 3D structure of the BsubPc unit with the axial substituent (Ra) and concave/convex sides of the bowl labelled. The peripheral substituents have been omitted from the 3D structure for clarity. |
BsubPcs are typically employed in the solid state as photoactive materials in organic electronics, sparking the interest in using X-ray diffraction (XRD) to study the intermolecular interactions that impact their solid-state arrangements (Virdo et al., 2016). The solid-state arrangement of BsubPcs can be described by the molecular fragment interactions between neighbouring BsubPcs and the relative alignment of the isoindoline fragments, with π–π interactions commonly being seen between adjacent BsubPcs in the (Bukuroshi et al., 2019). These interactions can provide information on the charge-transfer properties of BsubPcs, which is important for their application as organic semiconductors (Castrucci et al., 2012).
In this study, single crystals were grown of an array of BsubPcs with structurally diverse axial groups (Fig. 2) to investigate how the axial group impacts the π–π interactions of BsubPcs in the solid state and explore the intermolecular interactions that involve the axial group. The influence of the axial group on the BsubPc bowl depth and axial bond length is also of interest. While crystal structures of some of the BsubPcs investigated in this study have been reported previously, past studies have largely focused on smaller subsets of axial substituents, such as halide (Fulford et al., 2012), phenoxy (Paton et al., 2011) or sulfonate (Paton et al., 2012) derivatives, but different functional groups are rarely compared to each other. A review paper from Lavarda et al. (2022) provides a general summary of the crystal behaviour of axial halide, aryl and aryloxy derivatives, but the discussion does not extend to other boron–oxygen-bonded derivatives or include any boron–sulfur- or boron–nitrogen-bonded derivatives, and the crystals are from multiple laboratories. Therefore, herein, we provide the first report of a systematic comparison of BsubPc crystal structures with a comprehensive set of axial substituents, including halide (1 and 2), alkoxy (3–8), phenoxy (9 and 10), carboxylate (11 and 12), siloxy (13), thiophenoxy (14 and 15) and amino (16) derivatives. Furthermore, we report new polymorphs of some BsubPcs and use different crystal growth methods than have been reported previously.
![[Figure 2]](dg3059fig2thm.gif) | Figure 2 2D structures of investigated axially substituted BsubPcs with the colour of the axial group representing the heteroatom bonded to boron, i.e. chlorine – pink, bromine – purple, oxygen – blue, sulfur – red and nitrogen – green. |
2. Experimental
2.1. Materials and instrumentation
Toluene, heptane, acetone, dichloromethane (DCM), hexanes, tetrahydrofuran (THF) and pentane were purchased from Caledon Laboratories (Caledon, Ontario, Canada) and used as received. All X-ray data were collected using a Bruker Kappa APEX DUO CMOS Photon II diffractometer. Experimental and details are provided in Table 1. Structural analysis was conducted using Mercury software (Macrae et al., 2020).
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2.2. Synthesis and crystal growth
Briefly, with the exception of Br- and Cl-BsubPc, all other axially substituted BsubPcs were synthesized through an axial exchange reaction with Br-BsubPc and the appropriate In general, the axial exchange reactions were run in anhydrous chlorobenzene with 5–10 equivalents of the at 75 °C until all of the Br-BsubPc was consumed, as monitored by high-performance (HPLC). Full detailed synthetic procedures and characterization by 1H NMR and 19F NMR spectroscopy, direct analysis in real-time high-resolution (DART-HRMS) and HPLC for the BsubPcs analysed within this study are provided in a recent publication (Zigelstein & Bender, 2024).
The train apparatus that was used to grow several of the crystals analysed in this study has been described previously (Morse et al., 2010; Virdo et al., 2016). For crystals grown by slow vapour diffusion of heptane into toluene, 5–10 mg of material was dissolved in toluene in a 20 ml scintillation vial. The vial was then suspended in a sealed jar containing ∼150 ml of heptane and left undisturbed for 2–4 weeks until crystals were seen. For crystals grown by slow evaporation of a common organic solvent (i.e. acetone or methanol), 5–10 mg of material was dissolved in solvent in a 20 ml scintillation vial. The vial was then covered with aluminium foil with 3–5 holes poked through and left undisturbed until crystals were seen. For crystals grown during a two-solvent recrystallization, the material was dissolved in THF, and pentane was added dropwise until crystals formed out of solution. These crystals were then collected by gravity filtration. Finally, some crystals formed after rotary evaporation to remove DCM/hexanes after purification by on standard basic alumina. The crystal growth method used for each compound is provided in Table 1.
3. Results and discussion
Single crystals of 16 axially substituted BsubPcs were grown by either train slow vapour diffusion of heptane into toluene, slow evaporation of an organic solvent (i.e. acetone or methanol), two-solvent recrystallization or formed during rotary evaporation to remove solvent following purification by The influence of the axial group on the intermolecular interactions, bowl depths and axial bond lengths was analysed and is discussed below.
3.1. Intermolecular interactions
The previously established method for describing the intermolecular π–π interactions of BsubPcs uses some unique terminology for the side of the BsubPc bowl being considered and the alignment of isoindole units between adjacent BsubPcs (Morse et al., 2014; Virdo et al., 2016; Claessens et al., 2014; Farac et al., 2024). First, the terms concave and convex are used to describe the side of the BsubPc bowl being considered, with concave being the `inside' of the bowl and convex being the outer surface of the bowl [Fig. 1(c)]. Furthermore, the three outermost six-membered carbon rings of the BsubPc are called `heads', while the six-membered rings containing the boron centre, one imine N atom and two pyrrole N atoms are called `tails' [Fig. 1(b)] (Virdo et al., 2016). With these terms, the intermolecular π–π interactions of BsubPcs can be described as concave–concave, convex–convex, concave–convex, head-to-head, tail-to-tail and head-to-tail (Morse et al., 2010, 2014). Interactions between the axial ligand and BsubPc π-system are also sometimes observed and are described as concave-to-axial ligand and convex-to-axial ligand (Morse et al., 2010, 2014). Distances less than 4 Å are considered significant intermolecular π–π interactions (Fulford et al., 2012). All interactions involving a π-group are measured to the centroid of that group. Other interactions are considered significant if the intermolecular distance between the two atoms is less than the sum of the van der Waals radii of the two atoms (Virdo et al., 2013). For example, weak hydrogen bonds with C—H⋯O, C—H⋯F and C—H⋯N contacts are characterized by H⋯O, H⋯F and H⋯N distances less than 2.72, 2.67 and 2.75 Å, respectively. Furthermore, C—H⋯halogen bonds are characterized by H⋯Cl and H⋯Br distances that are less than 2.95 and 3.05 Å, respectively.
3.1.1. Axially halogenated BsubPcs
The of Cl-BsubPc [1; Fig. 3(a)] from train grown in this study shows good agreement with the previously reported structure (Virdo et al., 2016). It arranges in the orthorhombic Pnma with four molecules in the [Fig. 3(b)] [see Note 2]. There are significant convex–convex head-to-head interactions, with a πpyr–πPh distance (pyr is pyrrole and Ph is phenyl) of 3.615 Å, and less significant concave–concave head-to-tail interactions, with an intermolecular distance of 4.150 Å. There are also C—H⋯halogen interactions between the axial Cl and a πPh H atom of an adjacent molecule (C—HPh⋯Cl—B) at an intermolecular distance of 2.893 Å. Upon extension of the there are convex-to-axial ligand halogen–π (B—Cl⋯πPh) interactions, with an intermolecular distance of 3.548 Å. The intermolecular interactions of Cl-BsubPc (1) are shown in Fig. 3(c).
![[Figure 3]](dg3059fig3thm.gif) | Figure 3 (a) The molecular structure of Cl-BsubPc (1), with displacement ellipsoids drawn at the 50% probability level and H atoms removed for clarity, (b) the unit-cell packing and (c) significant intermolecular interactions in the π–π interactions are shown in blue and all other intermolecular interactions are shown in green. Atom colours: carbon – gray, hydrogen – white, nitrogen – blue, boron – light pink and chlorine – green. |
It has been reported previously that a Br-BsubPc [2; Fig. 4(a)] crystal cannot be grown by train because the boron–bromine axial bond (B—Br) is not thermally stable at its temperature (Fulford et al., 2012; Hildebrand et al., 2022). However, within this study, we were able to obtain a sublimed crystal of Br-BsubPc during the attempted purification of TMSO-BsubPc (13) by train (350 °C), as there was some unreacted Br-BsubPc remaining in the crude product from the TMSO-BsubPc axial exchange reaction, and therefore was separated and crystallized during train Like Cl-BsubPc, Br-BsubPc arranges in the orthorhombic Pnma with four molecules in the [Fig. 4(b)], which is consistent with the previously reported Br-BsubPc using solvent-based crystal growth methods (Fulford et al., 2012). The intermolecular interactions observed in the Br-BsubPc are very similar to those of the Cl-BsubPc Within the Br-BsubPc displays concave–concave head-to-tail packing, with an intermolecular distance of 4.151 Å, which is nearly identical to the distance observed for Cl-BsubPc. Upon extension outside the more significant π–π interactions are seen, with convex–convex head-to-head interactions between adjacent molecules at a πpyr–πPh distance of 3.661 Å. There are also C—H⋯halogen interactions between the axial Br atom and an adjacent πPh H atom (C—HPh⋯Br—B), with an intermolecular distance of 2.977 Å, which is slightly longer than what is seen in the Cl-BsubPc due to the larger size of bromine compared to chlorine. Convex-to-axial ligand halogen–π (B—Br⋯πPh) interactions are also observed, with an intermolecular distance of 3.475 Å. This is shorter than the distance observed for the analogous interaction for Cl-BsubPc. The intermolecular interactions of Br-BsubPc (2) are shown in Fig. 4(c).
![[Figure 4]](dg3059fig4thm.gif) | Figure 4 (a) The molecular structure of Br-BsubPc (2), with displacement ellipsoids drawn at the 50% probability level and H atoms removed for clarity, (b) the unit-cell packing and (c) significant intermolecular interactions in the π–π interactions are shown in blue and all other intermolecular interactions are shown in green. Atom colours: carbon – gray, hydrogen – white, nitrogen – blue, boron – light pink and bromine – bronze. |
3.1.2. Axial boron–oxygen-bonded BsubPcs
Crystals of MeO-BsubPc [3; Fig. 5(a)] were grown by train and arranged in the orthorhombic Pnma with four molecules in the [Fig. 5(b)]. The only π–π interactions are weak concave–concave head-to-tail interactions, with an intermolecular distance of 4.044 Å. There is weak hydrogen bonding between the axial O atom and an adjacent πPh H atom (C—HPh⋯O—B), with an intermolecular distance of 2.637 Å. Extending beyond the there is a convex-to-axial ligand C—Hax⋯πPh interaction, with an intermolecular distance of 2.605 Å. The intermolecular interactions of MeO-BsubPc (3) are shown in Fig. 5(c).
![[Figure 5]](dg3059fig5thm.gif) | Figure 5 (a) The molecular structure of MeO-BsubPc (3), with displacement ellipsoids drawn at the 50% probability level and H atoms removed for clarity, (b) the unit-cell packing and (c) significant intermolecular interactions in the π–π interactions are shown in blue, weak hydrogen bonds are shown in red and all other intermolecular interactions are shown in green. Atom colours: carbon – gray, hydrogen – white, nitrogen – blue, boron – light pink and oxygen – red. |
Crystals of EtO-BsubPc (4) were grown in two ways: train [4-I; Fig. 6(a)] and slow evaporation of acetone (4-II). The was the same by both crystal growth methods. EtO-BsubPc is the only compound in the array that crystallizes in the monoclinic P21/n Starting with 4-I, there are four molecules in the [Fig. 6(b)] and the only π–π interactions are concave–concave head-to-head interactions, with a πpyr–πPh distance of 3.574 Å. There is weak hydrogen bonding between the axial O atom and an adjacent πPh H atom (C—HPh⋯O—B), with an intermolecular distance of 2.682 Å, which is slightly longer than the analogous distance for MeO-BsubPc. Extending beyond the there is a concave-to-axial ligand C26—Hax⋯πPh interaction, with an intermolecular distance of 3.593 Å. EtO-BsubPc is the only compound in the array with this type of interaction. The intermolecular interactions of EtO-BsubPc (4-I) are shown in Fig. 6(c).
![[Figure 6]](dg3059fig6thm.gif) | Figure 6 (a) The molecular structure of EtO-BsubPc (4-I), with displacement ellipsoids drawn at the 50% probability level and H atoms removed for clarity, (b) the unit-cell packing and (c) significant intermolecular interactions in the π–π interactions are shown in blue, weak hydrogen bonds are shown in red and all other interactions are shown in green. Atom colours: carbon – gray, hydrogen – white, nitrogen – blue, boron – light pink and oxygen – red. |
As mentioned above, the of EtO-BsubPc from slow evaporation of acetone [4-II; Fig. 7(a)] was the same as the from train (4-I), arranging in the monoclinic P21/n with four molecules in the [Fig. 7(b)]. Identical intermolecular interactions were seen for 4-I and 4-II, with very modest differences in the intermolecular distances. The concave–concave head-to-head πpyr–πPh distance for 4-II (3.577 Å) was slightly longer than for 4-I (3.574 Å), whereas the concave-to-axial ligand C26—Hax⋯πPh intermolecular distance for 4-II (3.590 Å) was slightly shorter than for 4-I (3.593 Å). Lastly, the weak hydrogen bonding between the axial O atom and an adjacent πPh H atom (C—HPh⋯O—B) for 4-II (2.690 Å) was at a slightly longer intermolecular distance than for 4-I (2.682 Å). The intermolecular interactions of EtO-BsubPc (4-II) are shown in Fig. 7(c).
![[Figure 7]](dg3059fig7thm.gif) | Figure 7 (a) The molecular structure of EtO-BsubPc (4-II), with displacement ellipsoids drawn at the 50% probability level and H atoms removed for clarity, (b) the unit-cell packing and (c) significant intermolecular interactions in the π–π interactions are shown in blue, weak hydrogen bonds are shown in red and all other interactions are shown in green. Atom colours: carbon – gray, hydrogen – white, nitrogen – blue, boron – light pink and oxygen – red. |
F3EtO-BsubPc [5; Fig. 8(a)] crystals were grown by train organizing in the monoclinic P21/c with four molecules in the [Fig. 8(b)]. Similar to EtO-BsubPc, the most significant π–π interactions are concave–concave head-to-head interactions, although the πpyr–πPh distance is slightly longer at 3.640 Å. Unlike EtO-BsubPc, convex–convex head-to-tail interactions are observed, with an intermolecular distance of 3.822 Å. The axial group also has significant interactions, with weak hydrogen bonding between the axial O atom and an adjacent πPh H atom (C—HPh⋯O—B = 2.446 Å), an axial F atom with an adjacent πPh H atom (C—HPh⋯F—C = 2.529 Å) and an axial methylene H atom with an adjacent imine N atom (C25—Hax⋯Nimine = 2.622 Å). F3EtO-BsubPc is the only alkoxy derivative that does not contain any concave- or convex-to-axial ligand interactions, indicating that when H atoms are replaced with F atoms, weak hydrogen bonding dominates over axial–π interactions. The intermolecular interactions of F3EtO-BsubPc (5) are shown in Fig. 8(c).
![[Figure 8]](dg3059fig8thm.gif) | Figure 8 (a) The molecular structure of F3EtO-BsubPc (5), with displacement ellipsoids drawn at the 50% probability level and H atoms removed for clarity, (b) the unit-cell packing and (c) significant intermolecular interactions in the π–π interactions are shown in blue and weak hydrogen bonds are shown in red. Atom colours: carbon – gray, hydrogen – white, nitrogen – blue, boron – light pink, oxygen – red and fluorine – green. |
ButO-BsubPc [6; Fig. 9(a)] is the only compound in the array to crystallize in the orthorhombic Pbca with eight molecules in the [Fig. 9(b)]. There are significant concave–concave head-to-head interactions, with a πpyr–πPh distance of 3.612 Å, and less significant convex–convex head-to-tail interactions, with an intermolecular distance of 4.295 Å. There are also significant interactions involving the axial group, including weak hydrogen bonding between the axial O atom and a neighbouring πPh H atom (C—HPh⋯O—B = 2.556 Å), and between an axial methylene H atom and an adjacent imine N atom (C26—Hax⋯Nimine = 2.640 Å). There is also a convex-to-axial ligand C28—Hax⋯πPh interaction between an axial methyl H atom and the πPh group of a neighbouring molecule (3.319 Å). The intermolecular interactions of ButO-BsubPc (6) are shown in Fig. 9(c).
![[Figure 9]](dg3059fig9thm.gif) | Figure 9 (a) The molecular structure of ButO-BsubPc (6), with displacement ellipsoids drawn at the 50% probability level and H atoms removed for clarity, (b) the unit-cell packing and (c) significant intermolecular interactions in the π–π interactions are shown in blue, weak hydrogen bonds are shown in red and all other intermolecular interactions are shown in green. Atom colours: carbon – gray, hydrogen – white, nitrogen – blue, boron – light pink and oxygen – red. |
tButO-BsubPc [7; Fig. 10(a)] arranges in the monoclinic P21/c with four molecules in the [Fig. 10(b)]. Within the the only significant π–π interaction is a concave–concave head-to-head interaction, with a πpyr–πPh distance of 3.564 Å, which is shorter than the distance observed for EtO-BsubPc (4), F3EtO-BsubPc (5) and ButO-BsubPc (6). Upon extension of the there is a convex-to-axial ligand C27—Hax⋯πPh interaction between an axial H atom and an adjacent πPh group (3.057 Å). No hydrogen bonding is observed for tButO-BsubPc. The intermolecular interactions of tButO-BsubPc (7) are shown in Fig. 10(c).
![[Figure 10]](dg3059fig10thm.gif) | Figure 10 (a) The molecular structure of tButO-BsubPc (7), with displacement ellipsoids drawn at the 50% probability level and H atoms removed for clarity, (b) the unit-cell packing and (c) significant intermolecular interactions in the π–π interactions are shown in blue and all other intermolecular interactions are shown in green. Atom colours: carbon – gray, hydrogen – white, nitrogen – blue, boron – light pink and oxygen – red. |
A diffraction-quality crystal of OctO-BsubPc (8) was difficult to obtain, likely due to the length of the axial alkyl chain preventing close packing of neighbouring molecules. After several unsuccessful attempts to grow crystals by train and solvent-based methods, such as slow evaporation and slow vapour diffusion, diffraction-quality crystals of OctO-BsubPc were successfully grown by slow evaporation of methanol, arranging in the triclinic P![[\overline{1}]](teximages/dg3059fi1.svg){kind=small}
There are three independent OctO-BsubPc molecules in the which are referred to as 8-A [Fig. 11(a)], 8-B [Fig. 11(b)] and 8-C [Fig. 11(c)], and 0.5 molecules of water for every three molecules of OctO-BsubPc [Fig. 11(d)]. 8-B and 8-C have disorder in the octyl chains. Within the there appears to be concave–convex head-to-head packing between 8-A and 8-B, although the alignment is not perfect. The two πpyr–πPh distances between adjacent molecules are not the same, at 3.628 and 3.673 Å. There also appears to be a concave–convex head-to-tail interaction between 8-A and 8-C, with an intermolecular distance of 3.890 Å, but again, the alignment is not perfect between the two adjacent molecules. The length of the axial octyl chain is likely responsible for the lack of perfect alignment. There is weak hydrogen bond between the axial O atom of 8-A and a πPh H atom of the adjacent 8-B molecule (C—HPh⋯O—B), with an intermolecular distance of 2.641 Å. There is also hydrogen bonding between a water molecule and the imine N atom of an adjacent 8-A molecule (2.165 Å). Lastly, convex-to-axial ligand C—H⋯π interactions are observed between an axial H atom of 8-C and the πPh group of 8-B, with a C—Hax⋯πPh distance of 2.971 Å. The intermolecular interactions of OctO-BsubPc (8) are shown in Fig. 11(e).
![[Figure 11]](dg3059fig11thm.gif) | Figure 11 The molecular structures of (a) OctO-BsubPc molecule A (8-A), (b) OctO-BsubPc molecule B (8-B) and (c) OctO-BsubPc molecule C (8-C), with displacement ellipsoids drawn at the 50% probability and H atoms removed for clarity. (d) The unit-cell packing of 8 and (e) significant intermolecular interactions in the of 8. π–π interactions are shown in blue, strong and weak hydrogen bonds are shown in red, and all other intermolecular interactions are shown in green. Atom colours: carbon – gray, hydrogen – white, nitrogen – blue, boron – light pink and oxygen – red. |
Crystals of PhO-BsubPc [9; Fig. 12(a)] were grown by slow vapour diffusion of heptane into toluene, arranging in the triclinic P with two molecules in the [Fig. 12(b)], as was reported previously (Paton et al., 2011). While there are no π–π interactions within the upon extension, concave–concave head-to-head packing is observed, with a πpyr–πPh distance of 3.674 Å. There do not appear to be any π–π interactions between the axial group and the isoindole groups of adjacent molecules, or any other interactions involving the axial group. The intermolecular interactions of PhO-BsubPc (9) are shown in Fig. 12(c).
![[Figure 12]](dg3059fig12thm.gif) | Figure 12 (a) The molecular structure of PhO-BsubPc (9), with displacement ellipsoids drawn at the 50% probability level and H atoms removed for clarity, (b) the unit-cell packing and (c) significant intermolecular interactions in the π–π interactions are shown in blue. Atom colours: carbon – gray, hydrogen – white, nitrogen – blue, boron – light pink and oxygen – red. |
Crystals of naphthoxy-BsubPc [10; Fig. 13(a)] were grown by train and the resulting is identical to a previous report from our group (Paton et al., 2013). Naphthoxy-BsubPc arranges in the orthorhombic Pnma with four molecules in the [Fig. 13(b)]. The naphthoxy axial group causes a disruption in the π–π interactions of the isoindole units of neighbouring BsubPcs, instead containing concave-to-axial ligand π–π interactions between the centroid of the outer ring of the naphthoxy unit and the tail of the BsubPc, with an intermolecular distance of 3.813 Å. There is also weak hydrogen bonding between the axial O atom and a neighbouring πPh H atom (2.627 Å). The intermolecular interactions of naphthoxy-BsubPc (10) are shown in Fig. 13(c).
![[Figure 13]](dg3059fig13thm.gif) | Figure 13 (a) The molecular structure of naphthoxy-BsubPc (10), with displacement ellipsoids drawn at the 50% probability level and H atoms removed for clarity, (b) the unit-cell packing and (c) significant intermolecular interactions in the π–π interactions are shown in blue and weak hydrogen bonds are shown in red. Atom colours: carbon – gray, hydrogen – white, nitrogen – blue, boron – light pink and oxygen – red. |
Moving on to the carboxylate derivatives (11 and 12), crystals of acetate-BsubPc [11; Fig. 14(a)] were grown by train showing good agreement with the previously reported structure from slow vapour diffusion of heptane into toluene (Lessard & Bender, 2013). Acetate-BsubPc crystallizes in the triclinic P with two molecules in the [Fig. 14(b)]. Packing within the appears to be largely dictated by the axial-group interactions, with weak hydrogen bonding between the axial O atom and an adjacent πPh H atom (C—HPh⋯O—B = 2.581 Å), the axial carbonyl O atom and an adjacent πPh H atom (C—HPh⋯O=C = 2.628 Å), and an axial H atom and an adjacent imine N atom (C—Hax⋯Nimine = 2.635 Å). The only π–π interactions observed in the are convex–convex tail-to-tail interactions, with an intermolecular distance of 3.897 Å. Looking beyond the there are concave–concave head-to-head interactions, with a πpyr–πPh distance of 3.620 Å. The intermolecular interactions of acetate-BsubPc (11) are shown in Fig. 14(c).
![[Figure 14]](dg3059fig14thm.gif) | Figure 14 (a) The molecular structure of acetate-BsubPc (11), with displacement ellipsoids drawn at the 50% probability level and H atoms removed for clarity, (b) the unit-cell packing and (c) significant intermolecular interactions in the π–π interactions are shown in blue and weak hydrogen bonds are shown in red. Atom colours: carbon – gray, hydrogen – white, nitrogen – blue, boron – light pink and oxygen – red. |
Crystals of benzoate-BsubPc [12; Fig. 15(a)] were grown by train again showing good agreement with the previously reported structure from slow vapour diffusion of heptane into toluene (Lessard & Bender, 2013). Benzoate-BsubPc arranges in the monoclinic P21/c with four molecules in the [Fig. 15(b)], which is different from acetate-BsubPc. The benzoate axial group seems to disrupt the BsubPc π–π interactions, as only weak convex–convex head-to-tail interactions are observed, with an intermolecular distance of 4.163 Å. As with acetate-BsubPc, the most significant intermolecular interactions for benzoate-BsubPc involve the axial group. First, C—HPh⋯πax interactions are observed, with the closest intermolecular distances being 2.726 or 3.612 Å, depending on which molecules in the are being considered. Weak hydrogen bonding between the axial carbonyl O atom and adjacent πPh H atoms (C—HPh⋯O=C) is also observed, with intermolecular distances of 2.510 or 2.536 Å, depending on the molecules in the being considered. The intermolecular interactions of benzoate-BsubPc (12) are shown in Fig. 15(c).
![[Figure 15]](dg3059fig15thm.gif) | Figure 15 (a) The molecular structure of benzoate-BsubPc (12), with displacement ellipsoids drawn at the 50% probability level and H atoms removed for clarity, (b) the unit-cell packing and (c) significant intermolecular interactions in the π–π interactions are shown in blue, weak hydrogen bonds are shown in red and all other intermolecular interactions are shown in green. Atom colours: carbon – gray, hydrogen – white, nitrogen – blue, boron – light pink and oxygen – red. |
The packing of the crystal of TMSO-BsubPc [13; Fig. 16(a)] is analogous to that of tButO-BsubPc (7), with the only structural difference between the two compounds being the replacement of the quaternary C atom of the axial tert-butyl group in tButO-BsubPc with an Si atom in TMSO-BsubPc. The crystals of both compounds were grown serendipitously during rotary evaporation of DCM/hexanes following purification by Both arrange in the monoclinic P21/c with four molecules in the [Fig. 16(b)], and display concave–concave head-to-head packing. The intermolecular πpyr–πPh distance for TMSO-BsubPc (3.543 Å) is slightly shorter than for tButO-BsubPc, while the convex-to-axial ligand C26—Hax⋯πPh interaction has a slightly longer intermolecular distance (3.070 Å) for TMSO-BsubPc than for tButO-BsubPc. There is also weak hydrogen bonding observed between an axial H atom and an adjacent πPh H atom (C—HPh⋯O—B = 2.478 Å), which is not observed for tButO-BsubPc. This may result from the longer bond length between oxygen and silicon (1.638 Å) in TMSO-BsubPc compared to oxygen and carbon (1.440 Å) in tButO-BsubPc, allowing for closer interactions with the axial O atom due to less directly around the O atom. The intermolecular interactions of TMSO-BsubPc (13) are shown in Fig. 16(c).
![[Figure 16]](dg3059fig16thm.gif) | Figure 16 (a) The molecular structure of TMSO-BsubPc (13), with displacement ellipsoids drawn at the 50% probability level and H atoms removed for clarity, (b) the unit-cell packing and (c) significant intermolecular interactions in the π–π interactions are shown in blue, weak hydrogen bonds are shown in red and all other intermolecular interactions are shown in green. Atom colours: carbon – gray, hydrogen – white, nitrogen – blue, boron – light pink, oxygen – red and silicon – yellow. |
3.1.3. Axial boron–sulfur- and boron–nitrogen-bonded BsubPcs
Crystals of F5PhS-BsubPc (14) were grown by slow vapour diffusion of heptane into toluene. There are two crystallographically independent molecules in the which are referred to as 14-A [Fig. 17(a)] and 14-B [Fig. 17(b)]. F5PhS-BsubPc arranges in the triclinic P with four molecules in the [Fig. 17(c)]. Within the there is concave–convex head-to-tail packing between 14-A and 14-B, with an intermolecular distance of 3.958 Å. Upon extension of the significant concave-to-axial ligand π–π interactions are observed between the πPh group and the πax group, with an intermolecular distance of 3.525 Å. There is also an interaction between the axial S atom and the πax group of an adjacent molecule (πax⋯S—B), at a distance of 3.560 Å. Finally, weak hydrogen bonding is observed between an axial F atom and an adjacent πPh H atom (C—Fax⋯πPh), at a distance of 2.546 Å. The intermolecular interactions of F5PhS-BsubPc (14) are shown in Fig. 17(d).
![[Figure 17]](dg3059fig17thm.gif) | Figure 17 The molecular structures of (a) F5PhS-BsubPc molecule A (14-A) and (b) F5PhS-BsubPc molecule B (14-B), with displacement ellipsoids drawn at the 50% probability level and H atoms removed for clarity. (c) The unit-cell packing and (d) significant intermolecular interactions in the of 14. π–π interactions are shown in blue, weak hydrogen bonds are shown in red and all other intermolecular interactions are shown in green. Atom colours: carbon – gray, hydrogen – white, nitrogen – blue, boron – light pink, sulfur – orange and fluorine – green. |
MePhS-BsubPc (15) crystals were grown by slow vapour diffusion of heptane into toluene. There are three independent molecules in the that are referred to as 15-A [Fig. 18(a)], 15-B [Fig. 18(b)] and 15-C [Fig. 18(c)]. MePhS-BsubPc arranges in the monoclinic C2/c with 24 molecules in the [Fig. 18(d)]. This is a different polymorph than the previously reported of MePhS-BsubPc (Morse & Bender, 2012b). With 24 molecules in the many interactions are observed. First, there are concave–concave head-to-head interactions between two adjacent 15-A molecules, with a πpyr–πPh distance of 3.659 Å. Next, there are less significant concave–concave head-to-tail interactions between two adjacent 15-B molecules at an intermolecular distance of 4.040 Å. There is also a slightly offset convex–convex head-to-head interaction between molecules 15-B and 15-C, with inconsistent πpyr–πPh distances of 3.577 and 3.691 Å. The most significant overlap between isoindole groups in this interaction is between the adjacent πPh groups at a distance of 3.537 Å. A similar offset convex–convex head-to-head interaction is seen between 15-A and 15-B, with πpyr–πPh distances of 3.861 and 3.934 Å, and a πPh–πPh distance of 3.911 Å. There are also some significant interactions with the axial group. First, there is a concave-to-axial ligand interaction between 15-B and 15-C, with a π–π interaction observed between the axial arene group of 15-B and the `tail' of 15-C at a distance of 3.895 Å. There is also a convex-to-axial ligand interaction between the axial S atom of 15-A and the πPh group of an adjacent 15-C molecule (πPh⋯S—B) at a distance of 3.786 Å. Finally, there is a C31—Hax⋯πax interaction between two adjacent 15-A molecules involving an axial methyl H atom and an axial arene group at a distance of 2.876 Å. The intermolecular interactions of MePhS-BsubPc (15) are shown in Fig. 18(e).
![[Figure 18]](dg3059fig18thm.gif) | Figure 18 The molecular structures of (a) MePhS-BsubPc molecule A (15-A), (b) MePhS-BsubPc molecule B (15-B) and (c) MePhS-BsubPc molecule C (15-C), with displacement ellipsoids drawn at the 50% probability level and H atoms removed for clarity. (d) The unit-cell packing and (e) significant intermolecular interactions in the of 15. π–π interactions are shown in blue and all other intermolecular interactions are shown in green. Atom colours: carbon – gray, hydrogen – white, nitrogen – blue, boron – light pink and sulfur – orange. |
On two separate occasions, crystals of PhMeN-BsubPc were grown during a two-solvent recrystallization with THF and pentane, resulting in two different polymorphs. The first polymorph [16-I; Fig. 19(a)] crystallized in the triclinic P with two molecules in the [16-I (mol 1) and 16-I (mol 2)] and a partial occupancy water solvent molecule [Fig. 19(b)], which is aligned with a previous report (Morse & Bender, 2012b). The second polymorph [16-II; Fig. 20(a)] crystallized in the monoclinic P21/c with only one molecule in the and no water [Fig. 20(b)]. Both 16-I and 16-II have four molecules in the Concave–concave head-to-head interactions were seen within the for 16-I, with a πpyr–πPh distance of 3.705 Å. There is also hydrogen bonding between the water molecule and the imine N atoms of two adjacent BsubPc molecules. Upon extension of the there is a C—HPh,ax⋯πax interaction between adjacent axial groups, with an intermolecular distance of 3.048 Å. The intermolecular interactions of 16-I are shown in Fig. 19(c).
![[Figure 19]](dg3059fig19thm.gif) | Figure 19 (a) The molecular structure of PhMeN-BsubPc (16-I), with displacement ellipsoids drawn at the 50% probability level and H atoms removed for clarity, (b) the unit-cell packing and (c) significant intermolecular interactions in the π–π interactions are shown in blue, hydrogen bonding is shown in red and all other intermolecular interactions are shown in green. Atom colours: carbon – gray, hydrogen – white, nitrogen – blue and boron – light pink. |
![[Figure 20]](dg3059fig20thm.gif) | Figure 20 (a) The molecular structure of PhMeN-BsubPc (16-II), with displacement ellipsoids drawn at the 50% probability level and H atoms removed for clarity, (b) the unit-cell packing and (c) significant intermolecular interactions in the π–π interactions are shown in blue and all other intermolecular interactions are shown in green. Atom colours: carbon – gray, hydrogen – white, nitrogen – blue and boron – light pink. |
For another crystal of PhMeN-BsubPc (16-II), there are no significant π–π interactions between adjacent isoindole units within the The axial group appears to have a strong influence on the packing within the with the most significant interactions being a convex-to-axial ligand C31—Hax⋯πPh interaction between an axial methyl H atom and the adjacent πPh group (2.816 Å). Upon extension of the there are concave–concave head-to-head interactions, with a πPh–πpyr distance of 3.790 Å, which is slightly longer than the analogous distance observed for 16-I. The intermolecular interactions of 16-II are shown in Fig. 20(c).
3.1.4. Intermolecular interactions summary
The π–π interactions observed in the crystal structures of the investigated BsubPcs are summarized in Table 2, and all intermolecular interactions involving the axial group are summarized in Table 3. Concave–concave head-to-head interactions were the most common π–π interactions in the analyzed BsubPcs, observed in 10 of the 17 crystal structures (Table 2). Head-to-head interactions, whether concave–concave, convex–convex or concave–convex, tend to display closer packing than head-to-tail interactions. Only MeO- (3), naphthoxy- (10), benzoate- (12) and F5PhS-BsubPc (14) didn't display any head-to-head packing. Concave–convex interactions were rare, appearing only in the crystal structures of OctO- (8) and F5PhS-BsubPc (14).
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Regarding intermolecular interactions involving the axial group, convex-to-axial ligand interactions were quite common, appearing in nine of the investigated crystal structures. These interactions always involved a πPh group and either an axial H atom, which was common among the axial alkoxy derivatives (3–8), or the axial heteroatom bonded to boron, in the cases of Cl- (1), Br- (2) and MePhS-BsubPc (15). F3EtO-BsubPc (5) was the only alkoxy derivative that did not have any concave- or convex-to-axial ligand interactions. Its nonfluorinated analogue, EtO-BsubPc (4), displayed concave-to-axial ligand interactions between one of its axial methyl H atoms and an adjacent πPh group, but in the case of F3EtO-BsubPc (5), the axial methyl H atoms are all replaced by F atoms. The F atoms instead interacted with adjacent πPh H atoms through weak hydrogen bonding. Furthermore, neither carboxylate derivative (11 and 12) had any concave- or convex-to-axial ligand interactions. Both compounds have two O atoms in the axial group capable of weak hydrogen bonding, which appeared to dictate the axial-group interactions.
Weak hydrogen-bonding interactions were prevalent in compounds with boron–oxygen axial bonds (3–13). Of the alkoxy derivatives (3–8), only tButO-BsubPc (7) did not display any hydrogen bonding, likely due to steric effects. PhO-BsubPc (9) was the only other boron–oxygen-bonded compound that did not display any hydrogen bonding. It looked like there may have been weak hydrogen bonding between the axial O atom and an adjacent axial πPh H atom in the of 9, but the intermolecular O⋯H distance (2.766 Å) was slightly greater than the sum of the van der Waals radii of oxygen and hydrogen (2.72 Å). For the carboxylate derivatives, acetate-BsubPc (11) had weak hydrogen bonding involving both the axial O atom bonded to boron and the carbonyl O atom, whereas hydrogen bonding was only seen with the carbonyl O atom of benzoate-BsubPc (12). Hydrogen bonding involving the axial N atom of PhMeN-BsubPc (16) was not observed for either polymorph.
Among the six compounds containing an arene group within the axial moiety (9, 10, 12, 14, 15 and 16), three had π–π interactions involving the axial group. Most significantly, the only π–π interactions seen for naphthoxy-BsubPc (10) were concave-to-axial ligand πax–πtail interactions. The two thiophenoxy derivatives were the only other compounds to display π–π interactions involving the πax group. Interestingly, PhO-BsubPc (9) was the only investigated compound that didn't have any interactions involving the axial group. Finally, the two polymorphs of PhMeN-BsubPc (16) have different intermolecular interactions involving the axial group. Both have C—Hax⋯π interactions, but for 16-I this interaction is between an axial phenyl H atom and an adjacent πax group, while for 16-II this interaction is between an axial methyl H atom and an adjacent πPh group.
3.2. Axial bond length and BsubPc bowl depth
The influence of the axial group on the axial bond length was also of interest in this study. The axial bond length is the distance between boron and the heteroatom to which it is bonded. As expected, the axial bond length increased linearly as the atomic radius of the heteroatom bonded to boron increased (Fig. 21). In cases where multiple compounds had the same heteroatom, the average bond length was used to generate Fig. 21. The average axial bond length was 1.430 ± 0.020 Å for boron–oxygen bonds, 1.512 ± 0.002 Å for boron–nitrogen bonds, 1.884 Å for the boron–chlorine bond, 1.931 ± 0.021 Å for boron–sulfur bonds and 2.052 Å for the boron–bromine bond.
![[Figure 21]](dg3059fig21thm.gif) | Figure 21 Atomic radius of the heteroatom bonded to boron (oxygen – blue circle, nitrogen – green square, chlorine – pink triangle, sulfur – red diamond and bromine – purple X) versus the axial bond length. The boron–oxygen bond length is the average axial bond length of compounds 3–13 and the boron–sulfur bond length is the average axial bond length of compounds 14 and 15. |
Additional trends were observed when comparing the axial bond lengths of compounds with the same heteroatom. Within the compounds with boron–oxygen bonds (Fig. 22), the two carboxylate derivatives [acetate- (11) and benzoate-BsubPc (12)] had the longest axial bond lengths at 1.473 Å for both compounds. The two phenoxy derivatives [PhO- (9) and naphthoxy-BsubPc (10)] had the next highest axial bond lengths at 1.441 Å for both compounds. For the axial alkoxy derivatives (3–8), there was a general slight decrease in axial bond length as the length of the carbon chain increases. The exception was F3EtO-BsubPc (5), which had the longest axial bond length of the alkoxy derivatives at 1.437 Å. The axial bond lengths of the three OctO-BsubPc (8) molecules in the showed some variation, resulting in an average bond length of 1.414 ± 0.006 Å. The bond length of TMSO-BsubPc (13) was most closely aligned with ButO-BsubPc (6), with both compounds having an axial bond length of 1.415 Å.
![[Figure 22]](dg3059fig22thm.gif) | Figure 22 Axial bond lengths of the investigated BsubPcs with boron–oxygen axial bonds. |
For the two compounds with axial boron–sulfur bonds, the axial bond length of F5PhS-BsubPc (14) was longer than that of MePhS-BsubPc (15) (Fig. 23). This is similar to what was seen with the alkoxy derivatives (3–8), with the fluorine-containing axial group (5) having the longest axial bond length. These results indicate that F atoms in the axial group cause a slight lengthening of the axial bond. F5PhS-BsubPc (14) has two molecules in its with an average bond length of 1.957 ± 0.001 Å, and MePhS-BsubPc (15) has three molecules in its with an average bond length of 1.915 ± 0.006 Å.
![[Figure 23]](dg3059fig23thm.gif) | Figure 23 Axial bond lengths of the investigated BsubPcs with boron–sulfur axial bonds. |
Bowl depth is a measure of the degree of nonplanarity of the BsubPc macrocycle. The greater the bowl depth, the less planar the molecule. Three bowl depths were calculated for each BsubPc (Fig. 24) by measuring the distance between the B atom and (i) the plane defined by the three pyrrole N atoms (plane a, green), (ii) the plane defined by the three imine N atoms (plane b, blue), and (iii) the plane defined by the six outermost C atoms (plane c, red). The greatest variation in bowl depth across the axially substituted BsubPcs was seen when considering the distance between boron and plane c (Fig. 24). Very little variation was seen in bowl depth when considering the distance between boron and planes a and b (Fig. 24). Therefore, this discussion will focus on the bowl depth that is measured between boron and plane c.
![[Figure 24]](dg3059fig24thm.gif){kind=small} | Figure 24 (a) Bowl depth variation with different axial substituents. Three bowl depths are reported as the shortest distance between boron and plane a (green), boron and plane b (blue), and boron and plane c (red). (b) 3D structure of Cl-BsubPc defining planes a, b and c, and (c) 2D general BsubPc structure highlighting the atoms that define planes a, b and c. For compounds with multiple molecules in the (8, 14, 15 and 16-I), the reported bowl depths are an average of all the molecules in the asymmetric unit. |
Unlike for the axial bond length, the nature of the heteroatom bonded to boron did not have a clear influence on the BsubPc bowl depth. The axially halogenated derivatives [Cl- (1) and Br-BsubPc (2)] had two of the smallest bowl depths of the investigated compounds, although the nature of the halogen atom had an almost negligible impact. Acetate-BsubPc (11) was the only compound with a smaller bowl depth than the halogens and had the smallest bowl depth of all investigated compounds. Interestingly, the other investigated carboxylate derivative, benzoate-BsubPc (12), had the second largest bowl depth of all investigated BsubPcs, behind only naphthoxy-BsubPc (10). It appears that adding to otherwise identical axial substituents increases the bowl depth. For instance, naphthoxy-BsubPc (10), which has two arene sites in the axial position, has a larger bowl depth than PhO-BsubPc (9), which has one arene site in the axial position. Furthermore, benzoate-BsubPc (12) has a larger bowl depth than acetate-BsubPc (11), with the only difference being an arene in place of a methyl group.
While F3EtO-BsubPc (5) stuck out from the other alkoxy-BsubPc derivatives (3–8) with the longest bond length, it stuck out again here with the smallest bowl depth. Among the nonfluorinated alkoxy derivatives, there does not appear to be a clear correlation between the bowl depth and the length of the axial carbon chain. Furthermore, there was a minimal difference in the bowl depths of ButO- (6) and tButO-BsubPc (7), indicating that branching does not impact the bowl depth. However, the bowl depth of TMSO-BsubPc (13) was smaller than that of its structural analogue, tButO-BsubPc (7), indicating that the presence of an Si atom in place of a C atom has a modest impact on the planarity of the BsubPc.
The thiophenoxy derivatives (14 and 15) both have multiple molecules in their asymmetric units with varying bowl depths. For F5PhS-BsubPc (14), there are two independent molecules in the with an average bowl depth of 2.620 ± 0.131 Å. For MePhS-BsubPc (15), the average bowl depth of the three molecules is 2.553 ± 0.019 Å. Therefore, adding F atoms to the thiophenoxy axial group increases both the BsubPc bowl depth and the axial bond length, in contrast to what was seen when adding F atoms to the axial alkoxy group, whereby the bond length increased and the bowl depth decreased.
Finally, the two PhMeN-BsubPc (16) polymorphs have very similar bowl depths when comparing the average bowl depth of the two molecules in 16-I (2.586 ± 0.45 Å) to the bowl depth of 16-II (2.595 Å).
The axial bond lengths and BsubPc bowl depths are tabulated in Table 4.
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4. Conclusions
Overall, the axial-group interactions play a significant role in the crystal packing of BsubPcs, influencing the crystal system/space group and intermolecular interactions. Concave–concave head-to-head interactions were the most common π–π interactions in the crystal structures of the investigated BsubPcs, whereas axial-group interactions with adjacent isoindoline units tended to favour the convex side of the bowl. Weak hydrogen-bonding interactions are prevalent when the axial group contains O and/or F atoms, but the axial N atom in PhMeN-BsubPc did not participate in hydrogen bonding. This may be a result of as other investigated compounds with bulky axial groups, such as tButO-BsubPc and OctO-BsubPc, also disrupted some of the intermolecular interactions. The bulkiness of tButO-BsubPc disrupted hydrogen bonding with the axial O atom, while OctO-BsubPc disrupted the intermolecular π–π interactions. The presence of in the axial moiety can also have a significant impact, as π–π interactions involving the axial group are now possible. In particular, naphthoxy-, F5PhS- and MePhS-BsubPc all have concave-to-axial π–π interactions. Furthermore, the axial bond length increases linearly with the atomic radius of the heteroatom bonded to boron, and the presence of F atoms in the axial group tended to lengthen the axial bond. However, there is no clear trend in BsubPc bowl depth related to the axial group, with only a modest impact being observed. There were also no clear trends observed based on some of the crystal growth methods. The crystal structures of EtO-BsubPc from train (4-I) and slow evaporation of acetone (4-II) were identical, as were the crystal structures of acetate- (11) and benzoate-BsubPc (12) grown from train in this study compared to a previous report of the crystal structures from solvent-based crystal growth methods. Train is often the preferred crystal growth method, as it most closely mimics the vacuum deposition conditions used for the thin film fabrication in organic electronic applicants. However, in this case, the solvent-based crystal growth methods appeared to produce the same results as train The only observed solvent effects were when hygroscopic solvents methanol and THF were used to grow crystals of OctO- (8) and PhMeN-BsubPc (16-I), respectively, with water molecules incorporated into the crystal structures and hydrogen bonding with imine N atoms. Overall, the results of this study are useful for the nanoengineering of thin films of BsubPcs for their application in organic electronics.
Supporting information
contains datablocks d2344a_a, d23119a_a, d2368_a, d22127_a, d22128_a, d22126_a, d2365_a, d23115_a, d23123_a, d2335_a, d23108a_a, d22121a_a, d22123a_a, d23117_a, d23110_a, d23112_a_tw_sq, d2339_a, d22150_a, global. DOI: https://doi.org/10.1107/S2053229624006934/dg3059sup1.cif
Structure factors: contains datablock d2344a_a. DOI: https://doi.org/10.1107/S2053229624006934/dg3059d2344a_asup2.hkl
Structure factors: contains datablock d23119a_a. DOI: https://doi.org/10.1107/S2053229624006934/dg3059d23119a_asup3.hkl
Structure factors: contains datablock d2368_a. DOI: https://doi.org/10.1107/S2053229624006934/dg3059d2368_asup4.hkl
Structure factors: contains datablock d22127_a. DOI: https://doi.org/10.1107/S2053229624006934/dg3059d22127_asup5.hkl
Structure factors: contains datablock d22128_a. DOI: https://doi.org/10.1107/S2053229624006934/dg3059d22128_asup6.hkl
Structure factors: contains datablock d22126_a. DOI: https://doi.org/10.1107/S2053229624006934/dg3059d22126_asup7.hkl
Structure factors: contains datablock d2365_a. DOI: https://doi.org/10.1107/S2053229624006934/dg3059d2365_asup8.hkl
Structure factors: contains datablock d23115_a. DOI: https://doi.org/10.1107/S2053229624006934/dg3059d23115_asup9.hkl
Structure factors: contains datablock d23123_a. DOI: https://doi.org/10.1107/S2053229624006934/dg3059d23123_asup10.hkl
Structure factors: contains datablock d2335_a. DOI: https://doi.org/10.1107/S2053229624006934/dg3059d2335_asup11.hkl
Structure factors: contains datablock d23108a_a. DOI: https://doi.org/10.1107/S2053229624006934/dg3059d23108a_asup12.hkl
Structure factors: contains datablock d22121a_a. DOI: https://doi.org/10.1107/S2053229624006934/dg3059d22121a_asup13.hkl
Structure factors: contains datablock d22123a_a. DOI: https://doi.org/10.1107/S2053229624006934/dg3059d22123a_asup14.hkl
Structure factors: contains datablock d23117_a. DOI: https://doi.org/10.1107/S2053229624006934/dg3059d23117_asup15.hkl
Structure factors: contains datablock d23110_a. DOI: https://doi.org/10.1107/S2053229624006934/dg3059d23110_asup16.hkl
Structure factors: contains datablock d23112_a_tw_sq. DOI: https://doi.org/10.1107/S2053229624006934/dg3059d23112_a_tw_sqsup17.hkl
Structure factors: contains datablock d2339_a. DOI: https://doi.org/10.1107/S2053229624006934/dg3059d2339_asup18.hkl
Structure factors: contains datablock d22150_a. DOI: https://doi.org/10.1107/S2053229624006934/dg3059d22150_asup19.hkl
Computing details top
Chlorido(subphthalocyaninato)boron (d2344a_a) top
Crystal data top
| C24H12BClN6 | Dx = 1.558 Mg m−3 |
| Mr = 430.66 | Cu Kα radiation, λ = 1.54178 Å |
| Orthorhombic, Pnma | Cell parameters from 5394 reflections |
| a = 12.0315 (10) Å | θ = 5.7–65.5° |
| b = 14.8174 (13) Å | µ = 2.07 mm−1 |
| c = 10.3002 (8) Å | T = 150 K |
| V = 1836.3 (3) Å3 | Shard, pink |
| Z = 4 | 0.15 × 0.06 × 0.02 mm |
| F(000) = 880 |
Data collection top
| Bruker Kappa APEX-DUO CMOS PHOTON II diffractometer | 1416 reflections with I > 2σ(I) |
| Radiation source: Incoatec ImuS with multi-layer optics | Rint = 0.061 |
| φ and ω scans | θmax = 66.2°, θmin = 5.2° |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −14→14 |
| Tmin = 0.646, Tmax = 0.753 | k = −17→16 |
| 19930 measured reflections | l = −12→11 |
| 1647 independent reflections |
Refinement top
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.035 | H-atom parameters constrained |
| wR(F2) = 0.097 | w = 1/[σ2(Fo2) + (0.0494P)2 + 1.2852P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.06 | (Δ/σ)max = 0.001 |
| 1647 reflections | Δρmax = 0.24 e Å−3 |
| 151 parameters | Δρmin = −0.34 e Å−3 |
| 0 restraints |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| Cl1 | 0.18664 (5) | 0.250000 | 1.23875 (6) | 0.0214 (2) | |
| N1 | 0.00611 (17) | 0.250000 | 0.9063 (2) | 0.0187 (5) | |
| N2 | 0.16179 (12) | 0.32926 (10) | 0.99200 (14) | 0.0175 (4) | |
| N3 | 0.33419 (12) | 0.40660 (11) | 0.97328 (15) | 0.0203 (4) | |
| N4 | 0.32869 (17) | 0.250000 | 1.0229 (2) | 0.0189 (5) | |
| C1 | 0.06079 (14) | 0.32723 (13) | 0.93070 (17) | 0.0182 (4) | |
| C2 | 0.04565 (15) | 0.41770 (12) | 0.87898 (18) | 0.0184 (4) | |
| C3 | −0.04130 (16) | 0.45728 (13) | 0.80994 (18) | 0.0209 (4) | |
| H3A | −0.107253 | 0.424477 | 0.791349 | 0.025* | |
| C4 | −0.02881 (17) | 0.54552 (14) | 0.76936 (18) | 0.0237 (4) | |
| H4A | −0.087720 | 0.574001 | 0.723614 | 0.028* | |
| C5 | 0.06875 (16) | 0.59383 (14) | 0.79419 (19) | 0.0233 (4) | |
| H5A | 0.074040 | 0.654917 | 0.766882 | 0.028* | |
| C6 | 0.15769 (16) | 0.55449 (13) | 0.85768 (18) | 0.0216 (4) | |
| H6A | 0.224841 | 0.586872 | 0.871258 | 0.026* | |
| C7 | 0.14594 (15) | 0.46613 (13) | 0.90106 (17) | 0.0186 (4) | |
| C8 | 0.22237 (15) | 0.40490 (13) | 0.96506 (17) | 0.0189 (4) | |
| C9 | 0.38573 (15) | 0.32726 (13) | 0.99400 (17) | 0.0195 (4) | |
| C10 | 0.49870 (15) | 0.29805 (13) | 0.96453 (16) | 0.0199 (4) | |
| C11 | 0.59444 (16) | 0.34628 (14) | 0.93356 (18) | 0.0243 (4) | |
| H11 | 0.594751 | 0.410391 | 0.932401 | 0.029* | |
| C12 | 0.68919 (16) | 0.29719 (15) | 0.9045 (2) | 0.0286 (5) | |
| H12 | 0.755883 | 0.328435 | 0.884055 | 0.034* | |
| B1 | 0.2098 (3) | 0.250000 | 1.0579 (3) | 0.0193 (6) |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.0256 (4) | 0.0190 (3) | 0.0195 (3) | 0.000 | 0.0007 (2) | 0.000 |
| N1 | 0.0177 (11) | 0.0165 (11) | 0.0218 (11) | 0.000 | 0.0024 (9) | 0.000 |
| N2 | 0.0171 (7) | 0.0156 (8) | 0.0196 (8) | 0.0000 (6) | 0.0003 (6) | 0.0002 (6) |
| N3 | 0.0194 (8) | 0.0205 (8) | 0.0211 (8) | −0.0013 (6) | −0.0006 (6) | 0.0005 (7) |
| N4 | 0.0181 (11) | 0.0180 (12) | 0.0205 (11) | 0.000 | −0.0003 (9) | 0.000 |
| C1 | 0.0166 (9) | 0.0201 (9) | 0.0180 (9) | −0.0003 (8) | 0.0030 (7) | −0.0012 (8) |
| C2 | 0.0200 (9) | 0.0178 (10) | 0.0175 (9) | 0.0013 (8) | 0.0029 (7) | −0.0004 (7) |
| C3 | 0.0187 (9) | 0.0228 (10) | 0.0212 (10) | 0.0007 (8) | 0.0009 (8) | −0.0010 (8) |
| C4 | 0.0235 (10) | 0.0258 (11) | 0.0218 (10) | 0.0065 (8) | 0.0009 (8) | 0.0016 (8) |
| C5 | 0.0273 (10) | 0.0196 (10) | 0.0230 (10) | 0.0027 (8) | 0.0039 (8) | 0.0027 (8) |
| C6 | 0.0229 (9) | 0.0199 (10) | 0.0220 (10) | −0.0007 (8) | 0.0035 (8) | 0.0010 (8) |
| C7 | 0.0207 (9) | 0.0188 (9) | 0.0164 (9) | 0.0010 (8) | 0.0022 (7) | −0.0001 (7) |
| C8 | 0.0200 (9) | 0.0188 (9) | 0.0180 (9) | −0.0018 (7) | 0.0003 (7) | −0.0010 (8) |
| C9 | 0.0199 (9) | 0.0200 (10) | 0.0187 (9) | −0.0021 (8) | −0.0022 (7) | −0.0008 (8) |
| C10 | 0.0173 (9) | 0.0249 (10) | 0.0176 (9) | −0.0002 (8) | −0.0037 (7) | 0.0008 (8) |
| C11 | 0.0215 (9) | 0.0278 (11) | 0.0234 (10) | −0.0035 (8) | −0.0030 (8) | 0.0021 (9) |
| C12 | 0.0178 (9) | 0.0383 (12) | 0.0296 (11) | −0.0039 (9) | 0.0003 (8) | 0.0015 (10) |
| B1 | 0.0199 (15) | 0.0176 (15) | 0.0205 (15) | 0.000 | −0.0009 (12) | 0.000 |
Geometric parameters (Å, º) top
| Cl1—B1 | 1.884 (3) | C3—H3A | 0.9500 |
| N1—C1 | 1.344 (2) | C4—C5 | 1.398 (3) |
| N1—C1i | 1.344 (2) | C4—H4A | 0.9500 |
| N2—C8 | 1.365 (2) | C5—C6 | 1.383 (3) |
| N2—C1 | 1.370 (2) | C5—H5A | 0.9500 |
| N2—B1 | 1.474 (2) | C6—C7 | 1.391 (3) |
| N3—C9 | 1.346 (2) | C6—H6A | 0.9500 |
| N3—C8 | 1.348 (2) | C7—C8 | 1.450 (3) |
| N4—C9 | 1.367 (2) | C9—C10 | 1.458 (3) |
| N4—C9i | 1.367 (2) | C10—C11 | 1.393 (3) |
| N4—B1 | 1.475 (4) | C10—C10i | 1.424 (4) |
| C1—C2 | 1.454 (3) | C11—C12 | 1.385 (3) |
| C2—C3 | 1.394 (3) | C11—H11 | 0.9500 |
| C2—C7 | 1.422 (3) | C12—C12i | 1.399 (4) |
| C3—C4 | 1.381 (3) | C12—H12 | 0.9500 |
| C1—N1—C1i | 116.8 (2) | C7—C6—H6A | 121.0 |
| C8—N2—C1 | 113.45 (15) | C6—C7—C2 | 120.65 (17) |
| C8—N2—B1 | 122.57 (17) | C6—C7—C8 | 132.11 (18) |
| C1—N2—B1 | 122.83 (17) | C2—C7—C8 | 107.16 (16) |
| C9—N3—C8 | 116.95 (16) | N3—C8—N2 | 122.36 (17) |
| C9—N4—C9i | 113.7 (2) | N3—C8—C7 | 130.51 (17) |
| C9—N4—B1 | 122.66 (11) | N2—C8—C7 | 105.51 (15) |
| C9i—N4—B1 | 122.67 (11) | N3—C9—N4 | 122.31 (16) |
| N1—C1—N2 | 122.64 (17) | N3—C9—C10 | 130.96 (17) |
| N1—C1—C2 | 130.93 (17) | N4—C9—C10 | 105.34 (16) |
| N2—C1—C2 | 105.06 (15) | C11—C10—C10i | 120.87 (12) |
| C3—C2—C7 | 120.40 (17) | C11—C10—C9 | 131.78 (18) |
| C3—C2—C1 | 131.96 (17) | C10i—C10—C9 | 107.26 (11) |
| C7—C2—C1 | 107.47 (15) | C12—C11—C10 | 117.44 (19) |
| C4—C3—C2 | 118.09 (18) | C12—C11—H11 | 121.3 |
| C4—C3—H3A | 121.0 | C10—C11—H11 | 121.3 |
| C2—C3—H3A | 121.0 | C11—C12—C12i | 121.68 (12) |
| C3—C4—C5 | 121.38 (18) | C11—C12—H12 | 119.2 |
| C3—C4—H4A | 119.3 | C12i—C12—H12 | 119.2 |
| C5—C4—H4A | 119.3 | N2—B1—N2i | 105.6 (2) |
| C6—C5—C4 | 121.35 (19) | N2—B1—N4 | 105.51 (16) |
| C6—C5—H5A | 119.3 | N2i—B1—N4 | 105.52 (16) |
| C4—C5—H5A | 119.3 | N2—B1—Cl1 | 113.41 (14) |
| C5—C6—C7 | 118.04 (18) | N2i—B1—Cl1 | 113.41 (14) |
| C5—C6—H6A | 121.0 | N4—B1—Cl1 | 112.64 (19) |
| C1i—N1—C1—N2 | −7.7 (3) | C2—C7—C8—N3 | 158.19 (19) |
| C1i—N1—C1—C2 | 156.82 (14) | C6—C7—C8—N2 | 175.97 (19) |
| C8—N2—C1—N1 | 156.35 (18) | C2—C7—C8—N2 | −7.20 (19) |
| B1—N2—C1—N1 | −11.7 (3) | C8—N3—C9—N4 | −8.6 (3) |
| C8—N2—C1—C2 | −11.6 (2) | C8—N3—C9—C10 | 155.84 (18) |
| B1—N2—C1—C2 | −179.66 (18) | C9i—N4—C9—N3 | 157.11 (13) |
| N1—C1—C2—C3 | 14.9 (3) | B1—N4—C9—N3 | −11.8 (3) |
| N2—C1—C2—C3 | −178.50 (19) | C9i—N4—C9—C10 | −10.7 (3) |
| N1—C1—C2—C7 | −160.3 (2) | B1—N4—C9—C10 | −179.7 (2) |
| N2—C1—C2—C7 | 6.32 (19) | N3—C9—C10—C11 | 16.4 (3) |
| C7—C2—C3—C4 | −2.9 (3) | N4—C9—C10—C11 | −177.2 (2) |
| C1—C2—C3—C4 | −177.54 (19) | N3—C9—C10—C10i | −160.25 (17) |
| C2—C3—C4—C5 | 1.2 (3) | N4—C9—C10—C10i | 6.13 (16) |
| C3—C4—C5—C6 | 1.6 (3) | C10i—C10—C11—C12 | −0.7 (2) |
| C4—C5—C6—C7 | −2.5 (3) | C9—C10—C11—C12 | −177.04 (18) |
| C5—C6—C7—C2 | 0.8 (3) | C10—C11—C12—C12i | 0.7 (2) |
| C5—C6—C7—C8 | 177.25 (19) | C8—N2—B1—N2i | −140.31 (15) |
| C3—C2—C7—C6 | 1.9 (3) | C1—N2—B1—N2i | 26.6 (3) |
| C1—C2—C7—C6 | 177.79 (16) | C8—N2—B1—N4 | −28.8 (3) |
| C3—C2—C7—C8 | −175.32 (17) | C1—N2—B1—N4 | 138.10 (17) |
| C1—C2—C7—C8 | 0.52 (19) | C8—N2—B1—Cl1 | 94.9 (2) |
| C9—N3—C8—N2 | 7.9 (3) | C1—N2—B1—Cl1 | −98.15 (19) |
| C9—N3—C8—C7 | −155.37 (19) | C9—N4—B1—N2 | 28.2 (3) |
| C1—N2—C8—N3 | −154.88 (17) | C9i—N4—B1—N2 | −139.74 (19) |
| B1—N2—C8—N3 | 13.2 (3) | C9—N4—B1—N2i | 139.74 (19) |
| C1—N2—C8—C7 | 12.0 (2) | C9i—N4—B1—N2i | −28.2 (3) |
| B1—N2—C8—C7 | −179.94 (18) | C9—N4—B1—Cl1 | −96.0 (2) |
| C6—C7—C8—N3 | −18.6 (3) | C9i—N4—B1—Cl1 | 96.0 (2) |
| Symmetry code: (i) x, −y+1/2, z. |
Bromido(subphthalocyaninato)boron (d23119a_a) top
Crystal data top
| C24H12BBrN6 | Dx = 1.681 Mg m−3 |
| Mr = 475.12 | Mo Kα radiation, λ = 0.71073 Å |
| Orthorhombic, Pnma | Cell parameters from 9878 reflections |
| a = 12.0010 (6) Å | θ = 2.4–27.5° |
| b = 15.0617 (8) Å | µ = 2.22 mm−1 |
| c = 10.3879 (5) Å | T = 150 K |
| V = 1877.67 (16) Å3 | Shard, purple |
| Z = 4 | 0.27 × 0.16 × 0.14 mm |
| F(000) = 952 |
Data collection top
| Bruker Kappa APEX-DUO CMOS PHOTON II diffractometer | 1955 reflections with I > 2σ(I) |
| Radiation source: sealed tube with Bruker Triumph monochromator | Rint = 0.027 |
| φ and ω scans | θmax = 27.5°, θmin = 2.4° |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −15→13 |
| Tmin = 0.688, Tmax = 0.746 | k = −18→19 |
| 23127 measured reflections | l = −13→13 |
| 2243 independent reflections |
Refinement top
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.021 | H-atom parameters constrained |
| wR(F2) = 0.057 | w = 1/[σ2(Fo2) + (0.0231P)2 + 1.4706P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.09 | (Δ/σ)max = 0.001 |
| 2243 reflections | Δρmax = 0.38 e Å−3 |
| 151 parameters | Δρmin = −0.26 e Å−3 |
| 0 restraints |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| Br1 | 0.81550 (2) | 0.750000 | 0.24958 (2) | 0.01614 (7) | |
| N1 | 0.66674 (10) | 0.59579 (8) | 0.52765 (12) | 0.0161 (3) | |
| N2 | 0.83966 (10) | 0.67206 (8) | 0.50914 (12) | 0.0138 (2) | |
| N3 | 0.99565 (14) | 0.750000 | 0.59384 (17) | 0.0146 (3) | |
| N4 | 0.67202 (14) | 0.750000 | 0.47898 (17) | 0.0144 (4) | |
| C1 | 0.31111 (13) | 0.70352 (12) | 0.59788 (17) | 0.0258 (4) | |
| H1 | 0.244319 | 0.672743 | 0.618348 | 0.031* | |
| C2 | 0.40596 (13) | 0.65542 (11) | 0.56881 (15) | 0.0216 (3) | |
| H2 | 0.405645 | 0.592354 | 0.570221 | 0.026* | |
| C3 | 0.50217 (12) | 0.70269 (10) | 0.53733 (14) | 0.0172 (3) | |
| C4 | 0.61501 (12) | 0.67384 (10) | 0.50787 (14) | 0.0157 (3) | |
| C5 | 0.77859 (12) | 0.59742 (10) | 0.53537 (14) | 0.0147 (3) | |
| C6 | 0.85558 (12) | 0.53724 (10) | 0.59867 (14) | 0.0152 (3) | |
| C7 | 0.84333 (13) | 0.45010 (10) | 0.64201 (14) | 0.0175 (3) | |
| H7A | 0.776162 | 0.418167 | 0.627899 | 0.021* | |
| C8 | 0.93209 (13) | 0.41167 (10) | 0.70617 (16) | 0.0197 (3) | |
| H8A | 0.926535 | 0.351706 | 0.733810 | 0.024* | |
| C9 | 1.02985 (13) | 0.45920 (11) | 0.73121 (14) | 0.0196 (3) | |
| H9A | 1.088591 | 0.431358 | 0.777344 | 0.023* | |
| C10 | 1.04267 (12) | 0.54609 (10) | 0.69005 (14) | 0.0171 (3) | |
| H10A | 1.108779 | 0.578365 | 0.708496 | 0.021* | |
| C11 | 0.95604 (12) | 0.58479 (10) | 0.62094 (14) | 0.0146 (3) | |
| C12 | 0.94074 (11) | 0.67398 (10) | 0.56982 (14) | 0.0141 (3) | |
| B1 | 0.79108 (19) | 0.750000 | 0.4451 (2) | 0.0139 (4) |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Br1 | 0.02272 (12) | 0.01261 (11) | 0.01311 (11) | 0.000 | 0.00090 (8) | 0.000 |
| N1 | 0.0169 (6) | 0.0158 (6) | 0.0158 (6) | −0.0018 (5) | −0.0013 (5) | 0.0010 (5) |
| N2 | 0.0145 (6) | 0.0120 (6) | 0.0148 (6) | −0.0004 (5) | 0.0008 (5) | 0.0001 (5) |
| N3 | 0.0149 (8) | 0.0132 (8) | 0.0158 (8) | 0.000 | 0.0018 (7) | 0.000 |
| N4 | 0.0149 (8) | 0.0134 (8) | 0.0148 (8) | 0.000 | −0.0004 (7) | 0.000 |
| C1 | 0.0164 (7) | 0.0365 (10) | 0.0245 (8) | −0.0051 (7) | 0.0008 (6) | 0.0034 (7) |
| C2 | 0.0174 (7) | 0.0268 (8) | 0.0207 (8) | −0.0036 (6) | −0.0022 (6) | 0.0046 (7) |
| C3 | 0.0153 (7) | 0.0220 (8) | 0.0143 (7) | 0.0003 (6) | −0.0024 (6) | 0.0000 (6) |
| C4 | 0.0156 (7) | 0.0172 (7) | 0.0142 (7) | −0.0023 (6) | −0.0014 (5) | 0.0004 (6) |
| C5 | 0.0175 (7) | 0.0131 (7) | 0.0136 (7) | −0.0012 (5) | 0.0002 (5) | 0.0000 (5) |
| C6 | 0.0171 (7) | 0.0147 (7) | 0.0137 (6) | 0.0008 (6) | 0.0012 (6) | −0.0003 (5) |
| C7 | 0.0190 (7) | 0.0150 (7) | 0.0184 (7) | −0.0013 (6) | 0.0029 (6) | 0.0010 (6) |
| C8 | 0.0250 (8) | 0.0144 (7) | 0.0196 (7) | 0.0018 (6) | 0.0034 (6) | 0.0038 (6) |
| C9 | 0.0214 (7) | 0.0192 (7) | 0.0181 (7) | 0.0056 (6) | −0.0002 (6) | 0.0029 (6) |
| C10 | 0.0167 (7) | 0.0170 (7) | 0.0175 (7) | 0.0014 (6) | 0.0002 (6) | −0.0009 (6) |
| C11 | 0.0171 (6) | 0.0130 (7) | 0.0136 (7) | 0.0015 (5) | 0.0029 (5) | −0.0008 (5) |
| C12 | 0.0135 (6) | 0.0152 (7) | 0.0135 (7) | 0.0013 (5) | 0.0017 (5) | −0.0001 (6) |
| B1 | 0.0157 (10) | 0.0128 (10) | 0.0134 (11) | 0.000 | −0.0001 (9) | 0.000 |
Geometric parameters (Å, º) top
| Br1—B1 | 2.052 (2) | C2—H2 | 0.9500 |
| N1—C5 | 1.3449 (18) | C3—C3i | 1.425 (3) |
| N1—C4 | 1.3452 (19) | C3—C4 | 1.455 (2) |
| N2—C12 | 1.3674 (18) | C5—C6 | 1.452 (2) |
| N2—C5 | 1.3693 (18) | C6—C7 | 1.395 (2) |
| N2—B1 | 1.4698 (18) | C6—C11 | 1.421 (2) |
| N3—C12i | 1.3444 (17) | C7—C8 | 1.384 (2) |
| N3—C12 | 1.3444 (17) | C7—H7A | 0.9500 |
| N4—C4i | 1.3689 (17) | C8—C9 | 1.399 (2) |
| N4—C4 | 1.3689 (17) | C8—H8A | 0.9500 |
| N4—B1 | 1.471 (3) | C9—C10 | 1.385 (2) |
| C1—C2 | 1.383 (2) | C9—H9A | 0.9500 |
| C1—C1i | 1.400 (4) | C10—C11 | 1.391 (2) |
| C1—H1 | 0.9500 | C10—H10A | 0.9500 |
| C2—C3 | 1.395 (2) | C11—C12 | 1.456 (2) |
| C5—N1—C4 | 116.99 (13) | C11—C6—C5 | 107.39 (12) |
| C12—N2—C5 | 113.61 (12) | C8—C7—C6 | 117.89 (14) |
| C12—N2—B1 | 122.92 (13) | C8—C7—H7A | 121.1 |
| C5—N2—B1 | 122.24 (13) | C6—C7—H7A | 121.1 |
| C12i—N3—C12 | 116.79 (17) | C7—C8—C9 | 121.42 (14) |
| C4i—N4—C4 | 113.85 (17) | C7—C8—H8A | 119.3 |
| C4i—N4—B1 | 122.53 (9) | C9—C8—H8A | 119.3 |
| C4—N4—B1 | 122.53 (9) | C10—C9—C8 | 121.28 (14) |
| C2—C1—C1i | 121.60 (10) | C10—C9—H9A | 119.4 |
| C2—C1—H1 | 119.2 | C8—C9—H9A | 119.4 |
| C1i—C1—H1 | 119.2 | C9—C10—C11 | 118.17 (14) |
| C1—C2—C3 | 117.72 (16) | C9—C10—H10A | 120.9 |
| C1—C2—H2 | 121.1 | C11—C10—H10A | 120.9 |
| C3—C2—H2 | 121.1 | C10—C11—C6 | 120.44 (13) |
| C2—C3—C3i | 120.68 (10) | C10—C11—C12 | 131.98 (14) |
| C2—C3—C4 | 131.85 (15) | C6—C11—C12 | 107.38 (12) |
| C3i—C3—C4 | 107.38 (9) | N3—C12—N2 | 122.58 (13) |
| N1—C4—N4 | 122.35 (13) | N3—C12—C11 | 131.01 (14) |
| N1—C4—C3 | 131.18 (14) | N2—C12—C11 | 105.09 (12) |
| N4—C4—C3 | 105.13 (13) | N2i—B1—N2 | 106.01 (17) |
| N1—C5—N2 | 122.50 (13) | N2i—B1—N4 | 106.08 (12) |
| N1—C5—C6 | 130.60 (13) | N2—B1—N4 | 106.08 (12) |
| N2—C5—C6 | 105.19 (12) | N2i—B1—Br1 | 113.03 (11) |
| C7—C6—C11 | 120.73 (14) | N2—B1—Br1 | 113.03 (11) |
| C7—C6—C5 | 131.79 (14) | N4—B1—Br1 | 112.04 (15) |
| C1i—C1—C2—C3 | −0.93 (18) | C9—C10—C11—C6 | 2.7 (2) |
| C1—C2—C3—C3i | 0.92 (18) | C9—C10—C11—C12 | 176.81 (15) |
| C1—C2—C3—C4 | 176.97 (16) | C7—C6—C11—C10 | −2.1 (2) |
| C5—N1—C4—N4 | 8.8 (2) | C5—C6—C11—C10 | 174.79 (13) |
| C5—N1—C4—C3 | −155.92 (15) | C7—C6—C11—C12 | −177.45 (13) |
| C4i—N4—C4—N1 | −157.35 (11) | C5—C6—C11—C12 | −0.60 (16) |
| B1—N4—C4—N1 | 10.9 (3) | C12i—N3—C12—N2 | 8.0 (3) |
| C4i—N4—C4—C3 | 10.8 (2) | C12i—N3—C12—C11 | −156.87 (11) |
| B1—N4—C4—C3 | 179.12 (17) | C5—N2—C12—N3 | −156.66 (15) |
| C2—C3—C4—N1 | −15.9 (3) | B1—N2—C12—N3 | 10.9 (2) |
| C3i—C3—C4—N1 | 160.54 (14) | C5—N2—C12—C11 | 11.56 (16) |
| C2—C3—C4—N4 | 177.39 (17) | B1—N2—C12—C11 | 179.14 (15) |
| C3i—C3—C4—N4 | −6.17 (13) | C10—C11—C12—N3 | −14.1 (3) |
| C4—N1—C5—N2 | −7.8 (2) | C6—C11—C12—N3 | 160.59 (16) |
| C4—N1—C5—C6 | 155.00 (15) | C10—C11—C12—N2 | 179.12 (15) |
| C12—N2—C5—N1 | 154.60 (14) | C6—C11—C12—N2 | −6.23 (15) |
| B1—N2—C5—N1 | −13.1 (2) | C12—N2—B1—N2i | −25.6 (2) |
| C12—N2—C5—C6 | −11.95 (16) | C5—N2—B1—N2i | 140.89 (12) |
| B1—N2—C5—C6 | −179.63 (14) | C12—N2—B1—N4 | −138.14 (14) |
| N1—C5—C6—C7 | 18.5 (3) | C5—N2—B1—N4 | 28.4 (2) |
| N2—C5—C6—C7 | −176.44 (15) | C12—N2—B1—Br1 | 98.71 (15) |
| N1—C5—C6—C11 | −157.83 (15) | C5—N2—B1—Br1 | −94.76 (16) |
| N2—C5—C6—C11 | 7.19 (15) | C4i—N4—B1—N2i | 27.4 (2) |
| C11—C6—C7—C8 | −0.4 (2) | C4—N4—B1—N2i | −139.86 (15) |
| C5—C6—C7—C8 | −176.41 (15) | C4i—N4—B1—N2 | 139.86 (15) |
| C6—C7—C8—C9 | 2.2 (2) | C4—N4—B1—N2 | −27.4 (2) |
| C7—C8—C9—C10 | −1.5 (2) | C4i—N4—B1—Br1 | −96.36 (16) |
| C8—C9—C10—C11 | −1.0 (2) | C4—N4—B1—Br1 | 96.36 (16) |
| Symmetry code: (i) x, −y+3/2, z. |
(Methanolato)(subphthalocyaninato)boron (d2368_a) top
Crystal data top
| C25H15BN6O | Dx = 1.449 Mg m−3 |
| Mr = 426.24 | Cu Kα radiation, λ = 1.54178 Å |
| Orthorhombic, Pnma | Cell parameters from 8333 reflections |
| a = 12.3162 (11) Å | θ = 5.1–65.5° |
| b = 15.2325 (19) Å | µ = 0.75 mm−1 |
| c = 10.4151 (10) Å | T = 150 K |
| V = 1953.9 (4) Å3 | Shard, pink |
| Z = 4 | 0.10 × 0.04 × 0.02 mm |
| F(000) = 880 |
Data collection top
| Bruker Kappa APEX-DUO CMOs PHOTON II diffractometer | 1570 reflections with I > 2σ(I) |
| Radiation source: Icoatec ImuS with multi-layer optics | Rint = 0.057 |
| φ and ω scans | θmax = 66.0°, θmin = 5.1° |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −14→14 |
| Tmin = 0.659, Tmax = 0.753 | k = −17→17 |
| 27808 measured reflections | l = −12→11 |
| 1762 independent reflections |
Refinement top
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.032 | w = 1/[σ2(Fo2) + (0.0301P)2 + 0.6842P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.078 | (Δ/σ)max < 0.001 |
| S = 1.08 | Δρmax = 0.22 e Å−3 |
| 1762 reflections | Δρmin = −0.19 e Å−3 |
| 159 parameters | Extinction correction: SHELXL2019 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| 0 restraints | Extinction coefficient: 0.0026 (3) |
| Primary atom site location: structure-invariant direct methods |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | Occ. (<1) | |
| O1 | 0.74991 (10) | 0.750000 | 0.29681 (12) | 0.0284 (3) | |
| N1 | 0.96403 (12) | 0.750000 | 0.56717 (14) | 0.0249 (3) | |
| N2 | 0.80691 (8) | 0.67267 (7) | 0.49738 (10) | 0.0235 (3) | |
| N3 | 0.64054 (8) | 0.59780 (7) | 0.53777 (10) | 0.0266 (3) | |
| N4 | 0.64148 (12) | 0.750000 | 0.48741 (14) | 0.0248 (3) | |
| C1 | 0.90890 (10) | 0.67473 (8) | 0.54862 (12) | 0.0235 (3) | |
| C2 | 0.92753 (10) | 0.58766 (8) | 0.60186 (12) | 0.0240 (3) | |
| C3 | 1.01583 (10) | 0.55147 (8) | 0.66539 (13) | 0.0281 (3) | |
| H3A | 1.081703 | 0.583335 | 0.674325 | 0.034* | |
| C4 | 1.00543 (11) | 0.46789 (9) | 0.71533 (13) | 0.0316 (3) | |
| H4A | 1.065143 | 0.442124 | 0.759076 | 0.038* | |
| C5 | 0.90876 (11) | 0.42036 (9) | 0.70283 (13) | 0.0306 (3) | |
| H5A | 0.904612 | 0.362429 | 0.736277 | 0.037* | |
| C6 | 0.81926 (10) | 0.45637 (8) | 0.64260 (13) | 0.0276 (3) | |
| H6A | 0.753201 | 0.424472 | 0.636119 | 0.033* | |
| C7 | 0.82830 (10) | 0.54053 (8) | 0.59167 (12) | 0.0245 (3) | |
| C8 | 0.74954 (10) | 0.59952 (8) | 0.53308 (12) | 0.0246 (3) | |
| C9 | 0.58841 (10) | 0.67493 (8) | 0.52199 (12) | 0.0251 (3) | |
| C10 | 0.48053 (10) | 0.70324 (9) | 0.56126 (12) | 0.0274 (3) | |
| C11 | 0.38841 (10) | 0.65651 (10) | 0.59870 (13) | 0.0332 (3) | |
| H11 | 0.388003 | 0.594147 | 0.599794 | 0.040* | |
| C12 | 0.29788 (11) | 0.70410 (11) | 0.63409 (15) | 0.0406 (4) | |
| H12 | 0.233924 | 0.673711 | 0.659092 | 0.049* | |
| C13 | 0.84839 (16) | 0.750000 | 0.23075 (18) | 0.0316 (4) | |
| H13A | 0.836530 | 0.729920 | 0.142465 | 0.047* | 0.5 |
| H13B | 0.899536 | 0.710471 | 0.273802 | 0.047* | 0.5 |
| H13C | 0.878312 | 0.809608 | 0.229560 | 0.047* | 0.5 |
| B1 | 0.75398 (16) | 0.750000 | 0.43343 (19) | 0.0240 (4) |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0324 (7) | 0.0282 (7) | 0.0246 (7) | 0.000 | −0.0006 (5) | 0.000 |
| N1 | 0.0245 (7) | 0.0217 (8) | 0.0284 (8) | 0.000 | 0.0037 (6) | 0.000 |
| N2 | 0.0247 (6) | 0.0216 (6) | 0.0242 (6) | −0.0011 (4) | 0.0021 (4) | −0.0001 (4) |
| N3 | 0.0263 (6) | 0.0280 (6) | 0.0255 (6) | −0.0025 (4) | −0.0020 (4) | 0.0002 (5) |
| N4 | 0.0248 (8) | 0.0265 (8) | 0.0231 (8) | 0.000 | −0.0009 (6) | 0.000 |
| C1 | 0.0226 (6) | 0.0236 (7) | 0.0241 (6) | −0.0004 (5) | 0.0042 (5) | −0.0011 (5) |
| C2 | 0.0261 (6) | 0.0207 (6) | 0.0252 (6) | 0.0010 (5) | 0.0037 (5) | −0.0015 (5) |
| C3 | 0.0261 (6) | 0.0241 (7) | 0.0342 (7) | 0.0008 (5) | 0.0005 (5) | −0.0026 (5) |
| C4 | 0.0317 (7) | 0.0273 (7) | 0.0359 (8) | 0.0046 (6) | −0.0029 (6) | 0.0018 (6) |
| C5 | 0.0362 (7) | 0.0224 (7) | 0.0332 (7) | 0.0016 (6) | 0.0031 (6) | 0.0040 (5) |
| C6 | 0.0292 (7) | 0.0243 (7) | 0.0293 (7) | −0.0028 (5) | 0.0041 (5) | 0.0003 (5) |
| C7 | 0.0273 (6) | 0.0227 (7) | 0.0235 (6) | −0.0002 (5) | 0.0030 (5) | −0.0015 (5) |
| C8 | 0.0277 (6) | 0.0232 (6) | 0.0228 (6) | −0.0036 (5) | 0.0012 (5) | −0.0014 (5) |
| C9 | 0.0255 (6) | 0.0272 (7) | 0.0227 (6) | −0.0031 (5) | −0.0022 (5) | 0.0010 (5) |
| C10 | 0.0245 (6) | 0.0355 (7) | 0.0221 (6) | −0.0013 (5) | −0.0052 (5) | 0.0010 (5) |
| C11 | 0.0261 (7) | 0.0413 (8) | 0.0323 (7) | −0.0044 (6) | −0.0049 (6) | 0.0046 (6) |
| C12 | 0.0236 (7) | 0.0557 (9) | 0.0426 (8) | −0.0047 (6) | 0.0002 (6) | 0.0040 (7) |
| C13 | 0.0465 (12) | 0.0223 (9) | 0.0261 (10) | 0.000 | 0.0043 (9) | 0.000 |
| B1 | 0.0265 (10) | 0.0228 (10) | 0.0228 (10) | 0.000 | 0.0012 (8) | 0.000 |
Geometric parameters (Å, º) top
| O1—C13 | 1.394 (2) | C5—C6 | 1.3819 (19) |
| O1—B1 | 1.424 (2) | C5—H5A | 0.9500 |
| N1—C1i | 1.3465 (14) | C6—C7 | 1.3920 (18) |
| N1—C1 | 1.3466 (14) | C6—H6A | 0.9500 |
| N2—C1 | 1.3651 (16) | C7—C8 | 1.4563 (18) |
| N2—C8 | 1.3708 (16) | C9—C10 | 1.4555 (18) |
| N2—B1 | 1.5020 (16) | C10—C11 | 1.3950 (18) |
| N3—C8 | 1.3435 (16) | C10—C10i | 1.425 (3) |
| N3—C9 | 1.3489 (17) | C11—C12 | 1.380 (2) |
| N4—C9 | 1.3655 (15) | C11—H11 | 0.9500 |
| N4—C9i | 1.3656 (15) | C12—C12i | 1.398 (3) |
| N4—B1 | 1.495 (2) | C12—H12 | 0.9500 |
| C1—C2 | 1.4556 (17) | C13—H13A | 0.9800 |
| C2—C3 | 1.3872 (18) | C13—H13B | 0.9800 |
| C2—C7 | 1.4213 (17) | C13—H13C | 0.9800 |
| C3—C4 | 1.3813 (19) | C13—H13Ai | 0.980 (9) |
| C3—H3A | 0.9500 | C13—H13Bi | 0.980 (15) |
| C4—C5 | 1.3995 (19) | C13—H13Ci | 0.980 (5) |
| C4—H4A | 0.9500 | ||
| C13—O1—B1 | 117.55 (15) | C11—C10—C10i | 120.68 (8) |
| C1i—N1—C1 | 116.76 (15) | C11—C10—C9 | 132.06 (13) |
| C1—N2—C8 | 112.76 (10) | C10i—C10—C9 | 107.23 (7) |
| C1—N2—B1 | 123.69 (11) | C12—C11—C10 | 117.63 (14) |
| C8—N2—B1 | 122.28 (11) | C12—C11—H11 | 121.2 |
| C8—N3—C9 | 117.01 (11) | C10—C11—H11 | 121.2 |
| C9—N4—C9i | 113.74 (15) | C11—C12—C12i | 121.69 (9) |
| C9—N4—B1 | 122.87 (7) | C11—C12—H12 | 119.2 |
| C9i—N4—B1 | 122.87 (7) | C12i—C12—H12 | 119.2 |
| N1—C1—N2 | 122.66 (11) | O1—C13—H13A | 109.5 |
| N1—C1—C2 | 129.92 (12) | O1—C13—H13B | 109.5 |
| N2—C1—C2 | 105.85 (10) | H13A—C13—H13B | 109.5 |
| C3—C2—C7 | 120.59 (11) | O1—C13—H13C | 109.5 |
| C3—C2—C1 | 131.86 (12) | H13A—C13—H13C | 109.5 |
| C7—C2—C1 | 107.23 (11) | H13B—C13—H13C | 109.5 |
| C4—C3—C2 | 118.24 (12) | O1—C13—H13Ai | 109.5 (2) |
| C4—C3—H3A | 120.9 | H13A—C13—H13Ai | 36.4 |
| C2—C3—H3A | 120.9 | H13B—C13—H13Ai | 135.8 |
| C3—C4—C5 | 121.38 (12) | H13C—C13—H13Ai | 75.8 |
| C3—C4—H4A | 119.3 | O1—C13—H13Bi | 109.5 (3) |
| C5—C4—H4A | 119.3 | H13A—C13—H13Bi | 135.8 |
| C6—C5—C4 | 121.03 (12) | H13B—C13—H13Bi | 75.8 |
| C6—C5—H5A | 119.5 | H13C—C13—H13Bi | 36.4 |
| C4—C5—H5A | 119.5 | H13Ai—C13—H13Bi | 109.5 |
| C5—C6—C7 | 118.34 (12) | O1—C13—H13Ci | 109.47 (12) |
| C5—C6—H6A | 120.8 | H13A—C13—H13Ci | 75.8 |
| C7—C6—H6A | 120.8 | H13B—C13—H13Ci | 36.4 |
| C6—C7—C2 | 120.37 (12) | H13C—C13—H13Ci | 135.8 |
| C6—C7—C8 | 132.43 (12) | H13Ai—C13—H13Ci | 109.5 |
| C2—C7—C8 | 107.00 (11) | H13Bi—C13—H13Ci | 109.5 |
| N3—C8—N2 | 122.73 (11) | O1—B1—N4 | 110.07 (15) |
| N3—C8—C7 | 129.67 (11) | O1—B1—N2 | 117.29 (10) |
| N2—C8—C7 | 105.77 (10) | N4—B1—N2 | 103.62 (11) |
| N3—C9—N4 | 122.25 (11) | O1—B1—N2i | 117.28 (10) |
| N3—C9—C10 | 131.17 (12) | N4—B1—N2i | 103.62 (11) |
| N4—C9—C10 | 105.25 (11) | N2—B1—N2i | 103.30 (14) |
| C1i—N1—C1—N2 | 8.5 (2) | C2—C7—C8—N2 | 7.22 (13) |
| C1i—N1—C1—C2 | −155.07 (10) | C8—N3—C9—N4 | 7.75 (18) |
| C8—N2—C1—N1 | −155.14 (13) | C8—N3—C9—C10 | −157.04 (13) |
| B1—N2—C1—N1 | 12.2 (2) | C9i—N4—C9—N3 | −156.56 (9) |
| C8—N2—C1—C2 | 11.82 (13) | B1—N4—C9—N3 | 15.4 (2) |
| B1—N2—C1—C2 | 179.17 (12) | C9i—N4—C9—C10 | 11.64 (19) |
| N1—C1—C2—C3 | −14.3 (2) | B1—N4—C9—C10 | −176.44 (14) |
| N2—C1—C2—C3 | −179.94 (13) | N3—C9—C10—C11 | −17.8 (2) |
| N1—C1—C2—C7 | 159.10 (13) | N4—C9—C10—C11 | 175.53 (14) |
| N2—C1—C2—C7 | −6.56 (13) | N3—C9—C10—C10i | 160.09 (12) |
| C7—C2—C3—C4 | 1.61 (18) | N4—C9—C10—C10i | −6.63 (11) |
| C1—C2—C3—C4 | 174.26 (13) | C10i—C10—C11—C12 | 0.65 (15) |
| C2—C3—C4—C5 | −0.04 (19) | C9—C10—C11—C12 | 178.25 (13) |
| C3—C4—C5—C6 | −1.6 (2) | C10—C11—C12—C12i | −0.66 (15) |
| C4—C5—C6—C7 | 1.55 (19) | C13—O1—B1—N4 | 180.000 (1) |
| C5—C6—C7—C2 | 0.02 (18) | C13—O1—B1—N2 | −61.93 (13) |
| C5—C6—C7—C8 | −174.12 (13) | C13—O1—B1—N2i | 61.93 (13) |
| C3—C2—C7—C6 | −1.63 (18) | C9—N4—B1—O1 | 94.40 (13) |
| C1—C2—C7—C6 | −175.90 (11) | C9i—N4—B1—O1 | −94.40 (13) |
| C3—C2—C7—C8 | 173.85 (11) | C9—N4—B1—N2 | −31.80 (19) |
| C1—C2—C7—C8 | −0.42 (13) | C9i—N4—B1—N2 | 139.39 (12) |
| C9—N3—C8—N2 | −8.48 (17) | C9—N4—B1—N2i | −139.39 (12) |
| C9—N3—C8—C7 | 153.85 (13) | C9i—N4—B1—N2i | 31.80 (19) |
| C1—N2—C8—N3 | 153.87 (11) | C1—N2—B1—O1 | 103.19 (15) |
| B1—N2—C8—N3 | −13.69 (18) | C8—N2—B1—O1 | −90.62 (17) |
| C1—N2—C8—C7 | −12.08 (13) | C1—N2—B1—N4 | −135.32 (12) |
| B1—N2—C8—C7 | −179.64 (12) | C8—N2—B1—N4 | 30.86 (16) |
| C6—C7—C8—N3 | 17.3 (2) | C1—N2—B1—N2i | −27.49 (19) |
| C2—C7—C8—N3 | −157.40 (13) | C8—N2—B1—N2i | 138.69 (10) |
| C6—C7—C8—N2 | −178.07 (13) |
| Symmetry code: (i) x, −y+3/2, z. |
(Ethanolato)(subphthalocyaninato)boron (d22127_a) top
Crystal data top
| C26H17BN6O | F(000) = 912 |
| Mr = 440.26 | Dx = 1.417 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| a = 9.0313 (14) Å | Cell parameters from 6076 reflections |
| b = 14.220 (2) Å | θ = 2.5–26.0° |
| c = 16.474 (2) Å | µ = 0.09 mm−1 |
| β = 102.667 (4)° | T = 150 K |
| V = 2064.3 (5) Å3 | Plate, purple |
| Z = 4 | 0.21 × 0.12 × 0.03 mm |
Data collection top
| Bruker Kappa APEX-DUO CMOS PHOTON II diffractometer | 3311 reflections with I > 2σ(I) |
| Radiation source: sealed tube with Bruker Triumph Monochromator | Rint = 0.101 |
| φ and ω scans | θmax = 27.5°, θmin = 1.9° |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −11→11 |
| Tmin = 0.684, Tmax = 0.746 | k = −18→18 |
| 49575 measured reflections | l = −21→20 |
| 4744 independent reflections |
Refinement top
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.047 | H-atom parameters constrained |
| wR(F2) = 0.098 | w = 1/[σ2(Fo2) + (0.0401P)2 + 0.5512P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.04 | (Δ/σ)max < 0.001 |
| 4744 reflections | Δρmax = 0.21 e Å−3 |
| 308 parameters | Δρmin = −0.23 e Å−3 |
| 0 restraints |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.43092 (12) | 0.67237 (8) | 0.21540 (6) | 0.0226 (3) | |
| N1 | 0.45908 (14) | 0.58982 (9) | 0.34451 (8) | 0.0197 (3) | |
| N2 | 0.56828 (14) | 0.70834 (9) | 0.43968 (8) | 0.0209 (3) | |
| N3 | 0.34169 (14) | 0.73791 (9) | 0.33712 (8) | 0.0185 (3) | |
| N4 | 0.07319 (14) | 0.74430 (9) | 0.29173 (8) | 0.0200 (3) | |
| N5 | 0.20976 (14) | 0.60783 (9) | 0.26680 (8) | 0.0186 (3) | |
| N6 | 0.30979 (14) | 0.45416 (9) | 0.30217 (8) | 0.0211 (3) | |
| C1 | 0.43968 (17) | 0.49460 (11) | 0.34219 (10) | 0.0196 (3) | |
| C2 | 0.56971 (17) | 0.45745 (11) | 0.40263 (10) | 0.0212 (3) | |
| C3 | 0.62097 (18) | 0.36620 (12) | 0.42212 (10) | 0.0238 (4) | |
| H3A | 0.567321 | 0.313513 | 0.394840 | 0.029* | |
| C4 | 0.75308 (18) | 0.35475 (12) | 0.48276 (10) | 0.0262 (4) | |
| H4A | 0.792134 | 0.293223 | 0.495709 | 0.031* | |
| C5 | 0.82990 (19) | 0.43142 (12) | 0.52514 (10) | 0.0266 (4) | |
| H5A | 0.919487 | 0.420909 | 0.566683 | 0.032* | |
| C6 | 0.77830 (18) | 0.52271 (12) | 0.50793 (10) | 0.0247 (4) | |
| H6A | 0.829356 | 0.574522 | 0.538144 | 0.030* | |
| C7 | 0.64924 (17) | 0.53599 (11) | 0.44495 (10) | 0.0208 (3) | |
| C8 | 0.56794 (17) | 0.62028 (11) | 0.41016 (10) | 0.0202 (3) | |
| C9 | 0.44772 (17) | 0.76266 (11) | 0.40651 (10) | 0.0197 (3) | |
| C10 | 0.38257 (17) | 0.84138 (11) | 0.44307 (10) | 0.0192 (3) | |
| C11 | 0.43401 (18) | 0.89251 (11) | 0.51574 (10) | 0.0220 (4) | |
| H11A | 0.532128 | 0.881631 | 0.549515 | 0.026* | |
| C12 | 0.33899 (18) | 0.95956 (12) | 0.53769 (10) | 0.0241 (4) | |
| H12A | 0.373533 | 0.996338 | 0.586292 | 0.029* | |
| C13 | 0.19304 (18) | 0.97406 (11) | 0.48953 (10) | 0.0240 (4) | |
| H13A | 0.130921 | 1.021538 | 0.505329 | 0.029* | |
| C14 | 0.13725 (18) | 0.92083 (11) | 0.41948 (10) | 0.0224 (4) | |
| H14A | 0.036495 | 0.929469 | 0.388239 | 0.027* | |
| C15 | 0.23215 (17) | 0.85429 (11) | 0.39580 (9) | 0.0191 (3) | |
| C16 | 0.20517 (17) | 0.78150 (11) | 0.33235 (9) | 0.0192 (3) | |
| C17 | 0.07709 (17) | 0.65512 (11) | 0.26457 (9) | 0.0194 (3) | |
| C18 | −0.04156 (18) | 0.58441 (11) | 0.25035 (9) | 0.0197 (3) | |
| C19 | −0.19862 (18) | 0.59144 (12) | 0.24018 (9) | 0.0220 (4) | |
| H19A | −0.246991 | 0.650926 | 0.238807 | 0.026* | |
| C20 | −0.28115 (18) | 0.50930 (12) | 0.23222 (10) | 0.0250 (4) | |
| H20A | −0.388527 | 0.512614 | 0.223660 | 0.030* | |
| C21 | −0.21131 (19) | 0.42095 (12) | 0.23637 (10) | 0.0255 (4) | |
| H21A | −0.271955 | 0.365765 | 0.231144 | 0.031* | |
| C22 | −0.05506 (19) | 0.41275 (12) | 0.24797 (10) | 0.0232 (4) | |
| H22A | −0.007700 | 0.352779 | 0.251650 | 0.028* | |
| C23 | 0.03053 (17) | 0.49511 (11) | 0.25409 (9) | 0.0202 (3) | |
| C24 | 0.19339 (17) | 0.51235 (11) | 0.27071 (9) | 0.0196 (3) | |
| C25 | 0.34167 (18) | 0.70717 (12) | 0.13924 (10) | 0.0260 (4) | |
| H25A | 0.289154 | 0.765629 | 0.149550 | 0.031* | |
| H25B | 0.263941 | 0.660151 | 0.114554 | 0.031* | |
| C26 | 0.4441 (2) | 0.72668 (13) | 0.08048 (11) | 0.0318 (4) | |
| H26A | 0.382777 | 0.745504 | 0.026213 | 0.048* | |
| H26B | 0.501630 | 0.669782 | 0.074011 | 0.048* | |
| H26C | 0.514583 | 0.777464 | 0.102930 | 0.048* | |
| B1 | 0.3627 (2) | 0.65482 (13) | 0.28386 (11) | 0.0196 (4) |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0180 (6) | 0.0296 (6) | 0.0206 (6) | 0.0021 (5) | 0.0052 (5) | 0.0034 (5) |
| N1 | 0.0163 (7) | 0.0219 (7) | 0.0220 (7) | 0.0023 (5) | 0.0068 (5) | 0.0016 (6) |
| N2 | 0.0160 (7) | 0.0228 (7) | 0.0243 (7) | 0.0015 (6) | 0.0053 (6) | 0.0027 (6) |
| N3 | 0.0153 (6) | 0.0183 (7) | 0.0219 (7) | 0.0013 (5) | 0.0044 (5) | 0.0027 (5) |
| N4 | 0.0186 (7) | 0.0201 (7) | 0.0203 (7) | 0.0019 (5) | 0.0022 (5) | 0.0020 (5) |
| N5 | 0.0168 (7) | 0.0193 (7) | 0.0199 (7) | 0.0018 (5) | 0.0046 (5) | 0.0012 (5) |
| N6 | 0.0208 (7) | 0.0222 (7) | 0.0217 (7) | 0.0021 (6) | 0.0076 (6) | −0.0009 (6) |
| C1 | 0.0198 (8) | 0.0205 (8) | 0.0212 (8) | 0.0025 (6) | 0.0101 (6) | 0.0008 (6) |
| C2 | 0.0182 (8) | 0.0244 (9) | 0.0237 (8) | 0.0045 (7) | 0.0106 (7) | 0.0033 (7) |
| C3 | 0.0218 (9) | 0.0239 (9) | 0.0292 (9) | 0.0028 (7) | 0.0129 (7) | 0.0044 (7) |
| C4 | 0.0238 (9) | 0.0266 (9) | 0.0315 (9) | 0.0083 (7) | 0.0132 (7) | 0.0106 (7) |
| C5 | 0.0205 (9) | 0.0350 (10) | 0.0250 (9) | 0.0058 (7) | 0.0063 (7) | 0.0090 (7) |
| C6 | 0.0200 (8) | 0.0301 (10) | 0.0249 (9) | 0.0038 (7) | 0.0068 (7) | 0.0024 (7) |
| C7 | 0.0174 (8) | 0.0243 (9) | 0.0225 (8) | 0.0024 (7) | 0.0082 (6) | 0.0032 (7) |
| C8 | 0.0149 (8) | 0.0251 (9) | 0.0218 (8) | −0.0002 (7) | 0.0067 (6) | 0.0016 (7) |
| C9 | 0.0159 (8) | 0.0204 (8) | 0.0228 (8) | −0.0017 (6) | 0.0045 (6) | 0.0026 (7) |
| C10 | 0.0179 (8) | 0.0182 (8) | 0.0223 (8) | −0.0013 (6) | 0.0057 (6) | 0.0043 (6) |
| C11 | 0.0196 (8) | 0.0220 (9) | 0.0235 (8) | −0.0029 (7) | 0.0029 (7) | 0.0030 (7) |
| C12 | 0.0263 (9) | 0.0242 (9) | 0.0223 (8) | −0.0048 (7) | 0.0061 (7) | −0.0005 (7) |
| C13 | 0.0249 (9) | 0.0218 (9) | 0.0275 (9) | 0.0030 (7) | 0.0103 (7) | 0.0008 (7) |
| C14 | 0.0193 (8) | 0.0231 (9) | 0.0248 (8) | 0.0028 (7) | 0.0046 (7) | 0.0041 (7) |
| C15 | 0.0198 (8) | 0.0179 (8) | 0.0199 (8) | −0.0001 (6) | 0.0052 (6) | 0.0037 (6) |
| C16 | 0.0187 (8) | 0.0183 (8) | 0.0208 (8) | 0.0032 (6) | 0.0050 (6) | 0.0057 (6) |
| C17 | 0.0179 (8) | 0.0238 (9) | 0.0165 (8) | 0.0032 (6) | 0.0038 (6) | 0.0022 (6) |
| C18 | 0.0208 (8) | 0.0228 (8) | 0.0150 (7) | 0.0006 (7) | 0.0025 (6) | 0.0003 (6) |
| C19 | 0.0199 (8) | 0.0262 (9) | 0.0198 (8) | 0.0018 (7) | 0.0043 (7) | −0.0024 (7) |
| C20 | 0.0187 (8) | 0.0343 (10) | 0.0231 (9) | −0.0014 (7) | 0.0071 (7) | −0.0045 (7) |
| C21 | 0.0256 (9) | 0.0278 (9) | 0.0246 (9) | −0.0065 (7) | 0.0087 (7) | −0.0019 (7) |
| C22 | 0.0257 (9) | 0.0234 (9) | 0.0208 (8) | 0.0005 (7) | 0.0061 (7) | −0.0010 (7) |
| C23 | 0.0202 (8) | 0.0235 (9) | 0.0174 (8) | 0.0014 (7) | 0.0050 (6) | −0.0008 (7) |
| C24 | 0.0210 (8) | 0.0203 (8) | 0.0181 (8) | 0.0024 (7) | 0.0053 (6) | −0.0018 (6) |
| C25 | 0.0224 (9) | 0.0326 (10) | 0.0224 (9) | 0.0013 (7) | 0.0037 (7) | 0.0035 (7) |
| C26 | 0.0366 (10) | 0.0362 (10) | 0.0247 (9) | 0.0009 (8) | 0.0111 (8) | 0.0047 (8) |
| B1 | 0.0161 (9) | 0.0199 (9) | 0.0230 (9) | 0.0021 (7) | 0.0051 (7) | 0.0018 (7) |
Geometric parameters (Å, º) top
| O1—B1 | 1.421 (2) | C10—C11 | 1.391 (2) |
| O1—C25 | 1.4231 (18) | C10—C15 | 1.422 (2) |
| N1—C8 | 1.363 (2) | C11—C12 | 1.383 (2) |
| N1—C1 | 1.365 (2) | C11—H11A | 0.9500 |
| N1—B1 | 1.493 (2) | C12—C13 | 1.397 (2) |
| N2—C8 | 1.343 (2) | C12—H12A | 0.9500 |
| N2—C9 | 1.349 (2) | C13—C14 | 1.380 (2) |
| N3—C9 | 1.3665 (19) | C13—H13A | 0.9500 |
| N3—C16 | 1.3667 (19) | C14—C15 | 1.389 (2) |
| N3—B1 | 1.508 (2) | C14—H14A | 0.9500 |
| N4—C16 | 1.341 (2) | C15—C16 | 1.453 (2) |
| N4—C17 | 1.348 (2) | C17—C18 | 1.451 (2) |
| N5—C17 | 1.3675 (19) | C18—C19 | 1.395 (2) |
| N5—C24 | 1.369 (2) | C18—C23 | 1.422 (2) |
| N5—B1 | 1.504 (2) | C19—C20 | 1.376 (2) |
| N6—C1 | 1.342 (2) | C19—H19A | 0.9500 |
| N6—C24 | 1.349 (2) | C20—C21 | 1.401 (2) |
| C1—C2 | 1.462 (2) | C20—H20A | 0.9500 |
| C2—C3 | 1.392 (2) | C21—C22 | 1.387 (2) |
| C2—C7 | 1.425 (2) | C21—H21A | 0.9500 |
| C3—C4 | 1.387 (2) | C22—C23 | 1.395 (2) |
| C3—H3A | 0.9500 | C22—H22A | 0.9500 |
| C4—C5 | 1.395 (2) | C23—C24 | 1.457 (2) |
| C4—H4A | 0.9500 | C25—C26 | 1.504 (2) |
| C5—C6 | 1.387 (2) | C25—H25A | 0.9900 |
| C5—H5A | 0.9500 | C25—H25B | 0.9900 |
| C6—C7 | 1.393 (2) | C26—H26A | 0.9800 |
| C6—H6A | 0.9500 | C26—H26B | 0.9800 |
| C7—C8 | 1.456 (2) | C26—H26C | 0.9800 |
| C9—C10 | 1.455 (2) | ||
| B1—O1—C25 | 120.02 (12) | C13—C14—C15 | 118.29 (15) |
| C8—N1—C1 | 113.79 (13) | C13—C14—H14A | 120.9 |
| C8—N1—B1 | 123.21 (13) | C15—C14—H14A | 120.9 |
| C1—N1—B1 | 122.88 (13) | C14—C15—C10 | 120.57 (14) |
| C8—N2—C9 | 116.72 (13) | C14—C15—C16 | 132.13 (14) |
| C9—N3—C16 | 112.90 (13) | C10—C15—C16 | 106.94 (13) |
| C9—N3—B1 | 122.28 (13) | N4—C16—N3 | 122.79 (14) |
| C16—N3—B1 | 123.28 (13) | N4—C16—C15 | 129.08 (14) |
| C16—N4—C17 | 116.85 (13) | N3—C16—C15 | 105.95 (13) |
| C17—N5—C24 | 112.70 (13) | N4—C17—N5 | 122.71 (14) |
| C17—N5—B1 | 123.34 (13) | N4—C17—C18 | 129.32 (14) |
| C24—N5—B1 | 122.42 (13) | N5—C17—C18 | 105.98 (13) |
| C1—N6—C24 | 116.70 (13) | C19—C18—C23 | 120.87 (14) |
| N6—C1—N1 | 122.12 (14) | C19—C18—C17 | 131.71 (15) |
| N6—C1—C2 | 131.66 (14) | C23—C18—C17 | 107.27 (13) |
| N1—C1—C2 | 105.09 (13) | C20—C19—C18 | 117.76 (15) |
| C3—C2—C7 | 120.77 (14) | C20—C19—H19A | 121.1 |
| C3—C2—C1 | 132.15 (15) | C18—C19—H19A | 121.1 |
| C7—C2—C1 | 107.07 (13) | C19—C20—C21 | 121.87 (15) |
| C4—C3—C2 | 117.75 (16) | C19—C20—H20A | 119.1 |
| C4—C3—H3A | 121.1 | C21—C20—H20A | 119.1 |
| C2—C3—H3A | 121.1 | C22—C21—C20 | 121.05 (15) |
| C3—C4—C5 | 121.57 (16) | C22—C21—H21A | 119.5 |
| C3—C4—H4A | 119.2 | C20—C21—H21A | 119.5 |
| C5—C4—H4A | 119.2 | C21—C22—C23 | 118.06 (15) |
| C6—C5—C4 | 121.42 (15) | C21—C22—H22A | 121.0 |
| C6—C5—H5A | 119.3 | C23—C22—H22A | 121.0 |
| C4—C5—H5A | 119.3 | C22—C23—C18 | 120.36 (14) |
| C5—C6—C7 | 117.89 (16) | C22—C23—C24 | 132.50 (15) |
| C5—C6—H6A | 121.1 | C18—C23—C24 | 106.96 (13) |
| C7—C6—H6A | 121.1 | N6—C24—N5 | 122.92 (14) |
| C6—C7—C2 | 120.53 (15) | N6—C24—C23 | 129.70 (14) |
| C6—C7—C8 | 132.24 (15) | N5—C24—C23 | 105.85 (13) |
| C2—C7—C8 | 107.22 (13) | O1—C25—C26 | 108.79 (13) |
| N2—C8—N1 | 121.84 (14) | O1—C25—H25A | 109.9 |
| N2—C8—C7 | 131.61 (14) | C26—C25—H25A | 109.9 |
| N1—C8—C7 | 105.34 (13) | O1—C25—H25B | 109.9 |
| N2—C9—N3 | 123.14 (14) | C26—C25—H25B | 109.9 |
| N2—C9—C10 | 129.53 (14) | H25A—C25—H25B | 108.3 |
| N3—C9—C10 | 105.76 (13) | C25—C26—H26A | 109.5 |
| C11—C10—C15 | 120.18 (14) | C25—C26—H26B | 109.5 |
| C11—C10—C9 | 132.03 (14) | H26A—C26—H26B | 109.5 |
| C15—C10—C9 | 107.28 (13) | C25—C26—H26C | 109.5 |
| C12—C11—C10 | 118.44 (15) | H26A—C26—H26C | 109.5 |
| C12—C11—H11A | 120.8 | H26B—C26—H26C | 109.5 |
| C10—C11—H11A | 120.8 | O1—B1—N1 | 110.43 (13) |
| C11—C12—C13 | 121.05 (15) | O1—B1—N5 | 118.04 (14) |
| C11—C12—H12A | 119.5 | N1—B1—N5 | 103.11 (13) |
| C13—C12—H12A | 119.5 | O1—B1—N3 | 117.12 (14) |
| C14—C13—C12 | 121.35 (16) | N1—B1—N3 | 102.99 (13) |
| C14—C13—H13A | 119.3 | N5—B1—N3 | 103.27 (12) |
| C12—C13—H13A | 119.3 | ||
| C24—N6—C1—N1 | −6.1 (2) | C14—C15—C16—N4 | −17.3 (3) |
| C24—N6—C1—C2 | 159.88 (16) | C10—C15—C16—N4 | 155.65 (15) |
| C8—N1—C1—N6 | 156.73 (14) | C14—C15—C16—N3 | 179.45 (16) |
| B1—N1—C1—N6 | −19.4 (2) | C10—C15—C16—N3 | −7.64 (16) |
| C8—N1—C1—C2 | −12.44 (17) | C16—N4—C17—N5 | −9.2 (2) |
| B1—N1—C1—C2 | 171.41 (13) | C16—N4—C17—C18 | 152.47 (16) |
| N6—C1—C2—C3 | 19.7 (3) | C24—N5—C17—N4 | 154.08 (14) |
| N1—C1—C2—C3 | −172.63 (16) | B1—N5—C17—N4 | −12.1 (2) |
| N6—C1—C2—C7 | −160.56 (16) | C24—N5—C17—C18 | −11.23 (17) |
| N1—C1—C2—C7 | 7.15 (16) | B1—N5—C17—C18 | −177.40 (13) |
| C7—C2—C3—C4 | −1.2 (2) | N4—C17—C18—C19 | 18.0 (3) |
| C1—C2—C3—C4 | 178.56 (16) | N5—C17—C18—C19 | −178.01 (16) |
| C2—C3—C4—C5 | 2.2 (2) | N4—C17—C18—C23 | −157.53 (15) |
| C3—C4—C5—C6 | −0.6 (3) | N5—C17—C18—C23 | 6.46 (17) |
| C4—C5—C6—C7 | −1.9 (2) | C23—C18—C19—C20 | −1.3 (2) |
| C5—C6—C7—C2 | 2.8 (2) | C17—C18—C19—C20 | −176.34 (16) |
| C5—C6—C7—C8 | −178.47 (16) | C18—C19—C20—C21 | 1.8 (2) |
| C3—C2—C7—C6 | −1.3 (2) | C19—C20—C21—C22 | −0.6 (2) |
| C1—C2—C7—C6 | 178.86 (14) | C20—C21—C22—C23 | −1.0 (2) |
| C3—C2—C7—C8 | 179.69 (14) | C21—C22—C23—C18 | 1.4 (2) |
| C1—C2—C7—C8 | −0.12 (17) | C21—C22—C23—C24 | 175.98 (16) |
| C9—N2—C8—N1 | 6.2 (2) | C19—C18—C23—C22 | −0.3 (2) |
| C9—N2—C8—C7 | −159.34 (16) | C17—C18—C23—C22 | 175.85 (14) |
| C1—N1—C8—N2 | −156.42 (14) | C19—C18—C23—C24 | −176.08 (14) |
| B1—N1—C8—N2 | 19.7 (2) | C17—C18—C23—C24 | 0.04 (17) |
| C1—N1—C8—C7 | 12.39 (17) | C1—N6—C24—N5 | 10.3 (2) |
| B1—N1—C8—C7 | −171.47 (14) | C1—N6—C24—C23 | −153.46 (16) |
| C6—C7—C8—N2 | −18.5 (3) | C17—N5—C24—N6 | −155.86 (14) |
| C2—C7—C8—N2 | 160.30 (16) | B1—N5—C24—N6 | 10.5 (2) |
| C6—C7—C8—N1 | 174.22 (17) | C17—N5—C24—C23 | 11.24 (17) |
| C2—C7—C8—N1 | −6.97 (17) | B1—N5—C24—C23 | 177.55 (13) |
| C8—N2—C9—N3 | −11.0 (2) | C22—C23—C24—N6 | −15.7 (3) |
| C8—N2—C9—C10 | 152.64 (16) | C18—C23—C24—N6 | 159.39 (16) |
| C16—N3—C9—N2 | 156.63 (14) | C22—C23—C24—N5 | 178.39 (16) |
| B1—N3—C9—N2 | −9.6 (2) | C18—C23—C24—N5 | −6.51 (16) |
| C16—N3—C9—C10 | −10.29 (17) | B1—O1—C25—C26 | 175.44 (14) |
| B1—N3—C9—C10 | −176.52 (13) | C25—O1—B1—N1 | 160.56 (13) |
| N2—C9—C10—C11 | 10.6 (3) | C25—O1—B1—N5 | 42.4 (2) |
| N3—C9—C10—C11 | 176.42 (16) | C25—O1—B1—N3 | −82.04 (18) |
| N2—C9—C10—C15 | −160.93 (15) | C8—N1—B1—O1 | 91.45 (17) |
| N3—C9—C10—C15 | 4.84 (17) | C1—N1—B1—O1 | −92.76 (17) |
| C15—C10—C11—C12 | −3.8 (2) | C8—N1—B1—N5 | −141.56 (14) |
| C9—C10—C11—C12 | −174.54 (16) | C1—N1—B1—N5 | 34.24 (19) |
| C10—C11—C12—C13 | 1.8 (2) | C8—N1—B1—N3 | −34.36 (19) |
| C11—C12—C13—C14 | 1.4 (2) | C1—N1—B1—N3 | 141.43 (14) |
| C12—C13—C14—C15 | −2.4 (2) | C17—N5—B1—O1 | −102.86 (17) |
| C13—C14—C15—C10 | 0.3 (2) | C24—N5—B1—O1 | 92.29 (18) |
| C13—C14—C15—C16 | 172.45 (16) | C17—N5—B1—N1 | 135.14 (14) |
| C11—C10—C15—C14 | 2.8 (2) | C24—N5—B1—N1 | −29.72 (18) |
| C9—C10—C15—C14 | 175.61 (14) | C17—N5—B1—N3 | 28.15 (19) |
| C11—C10—C15—C16 | −171.05 (14) | C24—N5—B1—N3 | −136.70 (14) |
| C9—C10—C15—C16 | 1.71 (17) | C9—N3—B1—O1 | −92.20 (17) |
| C17—N4—C16—N3 | 8.8 (2) | C16—N3—B1—O1 | 103.01 (17) |
| C17—N4—C16—C15 | −152.04 (15) | C9—N3—B1—N1 | 29.17 (19) |
| C9—N3—C16—N4 | −153.22 (14) | C16—N3—B1—N1 | −135.62 (14) |
| B1—N3—C16—N4 | 12.8 (2) | C9—N3—B1—N5 | 136.25 (14) |
| C9—N3—C16—C15 | 11.38 (17) | C16—N3—B1—N5 | −28.55 (19) |
| B1—N3—C16—C15 | 177.45 (13) |
(Ethanolato)(subphthalocyaninato)boron (d22128_a) top
Crystal data top
| C26H17BN6O | F(000) = 912 |
| Mr = 440.26 | Dx = 1.416 Mg m−3 |
| Monoclinic, P21/n | Cu Kα radiation, λ = 1.54178 Å |
| a = 9.0304 (5) Å | Cell parameters from 9939 reflections |
| b = 14.2423 (8) Å | θ = 4.2–65.7° |
| c = 16.4452 (9) Å | µ = 0.72 mm−1 |
| β = 102.476 (3)° | T = 150 K |
| V = 2065.1 (2) Å3 | Block, purple |
| Z = 4 | 0.15 × 0.15 × 0.10 mm |
Data collection top
| Bruker Kappa APEX-DUO CMOS PHOTON II diffractometer | 3148 reflections with I > 2σ(I) |
| Radiation source: Incoatec ImuS with multi-layer optics | Rint = 0.059 |
| φ and ω scans | θmax = 66.1°, θmin = 4.2° |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −10→10 |
| Tmin = 0.654, Tmax = 0.753 | k = −16→16 |
| 46104 measured reflections | l = −19→19 |
| 3555 independent reflections |
Refinement top
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
| wR(F2) = 0.102 | w = 1/[σ2(Fo2) + (0.0501P)2 + 0.8523P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.05 | (Δ/σ)max < 0.001 |
| 3555 reflections | Δρmax = 0.50 e Å−3 |
| 308 parameters | Δρmin = −0.21 e Å−3 |
| 0 restraints |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.43100 (11) | 0.67170 (7) | 0.21518 (6) | 0.0284 (3) | |
| N1 | 0.45941 (13) | 0.58926 (9) | 0.34451 (8) | 0.0247 (3) | |
| N2 | 0.56875 (13) | 0.70791 (9) | 0.43942 (8) | 0.0270 (3) | |
| N3 | 0.34174 (13) | 0.73692 (8) | 0.33710 (8) | 0.0243 (3) | |
| N4 | 0.07299 (13) | 0.74350 (9) | 0.29183 (8) | 0.0253 (3) | |
| N5 | 0.20962 (13) | 0.60716 (9) | 0.26691 (7) | 0.0241 (3) | |
| N6 | 0.31011 (14) | 0.45375 (9) | 0.30233 (8) | 0.0264 (3) | |
| C1 | 0.44029 (16) | 0.49430 (10) | 0.34227 (9) | 0.0253 (3) | |
| C2 | 0.57050 (16) | 0.45711 (11) | 0.40250 (9) | 0.0264 (3) | |
| C3 | 0.62145 (17) | 0.36615 (11) | 0.42205 (10) | 0.0300 (4) | |
| H3A | 0.567517 | 0.313576 | 0.394978 | 0.036* | |
| C4 | 0.75388 (18) | 0.35451 (12) | 0.48250 (10) | 0.0331 (4) | |
| H4A | 0.793009 | 0.293066 | 0.495193 | 0.040* | |
| C5 | 0.83088 (18) | 0.43129 (12) | 0.52509 (10) | 0.0339 (4) | |
| H5A | 0.920282 | 0.420810 | 0.566635 | 0.041* | |
| C6 | 0.77923 (17) | 0.52228 (12) | 0.50784 (10) | 0.0305 (4) | |
| H6A | 0.830297 | 0.574069 | 0.537896 | 0.037* | |
| C7 | 0.64952 (16) | 0.53554 (11) | 0.44475 (9) | 0.0271 (3) | |
| C8 | 0.56827 (15) | 0.61983 (11) | 0.40996 (9) | 0.0255 (3) | |
| C9 | 0.44810 (16) | 0.76202 (10) | 0.40642 (9) | 0.0252 (3) | |
| C10 | 0.38312 (16) | 0.84085 (10) | 0.44303 (9) | 0.0260 (3) | |
| C11 | 0.43452 (17) | 0.89237 (11) | 0.51549 (10) | 0.0292 (3) | |
| H11A | 0.532775 | 0.881930 | 0.549059 | 0.035* | |
| C12 | 0.33929 (18) | 0.95902 (11) | 0.53744 (10) | 0.0304 (4) | |
| H12A | 0.373671 | 0.995742 | 0.586086 | 0.036* | |
| C13 | 0.19338 (18) | 0.97357 (11) | 0.48956 (10) | 0.0310 (4) | |
| H13A | 0.131530 | 1.021163 | 0.505424 | 0.037* | |
| C14 | 0.13711 (17) | 0.92004 (11) | 0.41949 (10) | 0.0288 (3) | |
| H14A | 0.036258 | 0.928440 | 0.388532 | 0.035* | |
| C15 | 0.23225 (16) | 0.85365 (10) | 0.39565 (9) | 0.0252 (3) | |
| C16 | 0.20527 (16) | 0.78083 (10) | 0.33249 (9) | 0.0245 (3) | |
| C17 | 0.07694 (16) | 0.65457 (10) | 0.26476 (9) | 0.0241 (3) | |
| C18 | −0.04180 (16) | 0.58398 (10) | 0.25038 (9) | 0.0250 (3) | |
| C19 | −0.19910 (16) | 0.59083 (11) | 0.24007 (9) | 0.0276 (3) | |
| H19A | −0.247657 | 0.650166 | 0.238637 | 0.033* | |
| C20 | −0.28149 (17) | 0.50859 (12) | 0.23204 (10) | 0.0305 (4) | |
| H20A | −0.388824 | 0.511746 | 0.223543 | 0.037* | |
| C21 | −0.21143 (18) | 0.42064 (12) | 0.23607 (10) | 0.0310 (4) | |
| H21A | −0.272034 | 0.365522 | 0.230474 | 0.037* | |
| C22 | −0.05515 (17) | 0.41233 (11) | 0.24806 (9) | 0.0287 (3) | |
| H22A | −0.007766 | 0.352455 | 0.251932 | 0.034* | |
| C23 | 0.03028 (17) | 0.49473 (11) | 0.25427 (9) | 0.0254 (3) | |
| C24 | 0.19340 (16) | 0.51184 (10) | 0.27080 (9) | 0.0248 (3) | |
| C25 | 0.34110 (18) | 0.70714 (12) | 0.13931 (10) | 0.0342 (4) | |
| H25A | 0.289660 | 0.765756 | 0.150133 | 0.041* | |
| H25B | 0.262630 | 0.660635 | 0.114787 | 0.041* | |
| C26 | 0.4432 (2) | 0.72616 (13) | 0.08009 (11) | 0.0404 (4) | |
| H26A | 0.381919 | 0.745375 | 0.025975 | 0.061* | |
| H26B | 0.499809 | 0.669051 | 0.073209 | 0.061* | |
| H26C | 0.514504 | 0.776445 | 0.102470 | 0.061* | |
| B1 | 0.36277 (18) | 0.65409 (12) | 0.28368 (11) | 0.0248 (4) |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0225 (5) | 0.0359 (6) | 0.0268 (5) | 0.0022 (4) | 0.0054 (4) | 0.0042 (5) |
| N1 | 0.0205 (6) | 0.0268 (7) | 0.0269 (7) | 0.0030 (5) | 0.0054 (5) | 0.0020 (5) |
| N2 | 0.0208 (6) | 0.0287 (7) | 0.0310 (7) | 0.0007 (5) | 0.0048 (5) | 0.0029 (5) |
| N3 | 0.0212 (6) | 0.0247 (6) | 0.0265 (7) | 0.0010 (5) | 0.0041 (5) | 0.0032 (5) |
| N4 | 0.0235 (6) | 0.0265 (7) | 0.0250 (6) | 0.0020 (5) | 0.0029 (5) | 0.0022 (5) |
| N5 | 0.0215 (6) | 0.0253 (6) | 0.0254 (6) | 0.0021 (5) | 0.0049 (5) | 0.0007 (5) |
| N6 | 0.0239 (6) | 0.0280 (7) | 0.0279 (7) | 0.0039 (5) | 0.0071 (5) | 0.0005 (5) |
| C1 | 0.0236 (7) | 0.0267 (8) | 0.0272 (8) | 0.0033 (6) | 0.0090 (6) | 0.0009 (6) |
| C2 | 0.0230 (7) | 0.0305 (8) | 0.0275 (8) | 0.0047 (6) | 0.0096 (6) | 0.0045 (6) |
| C3 | 0.0282 (8) | 0.0308 (8) | 0.0334 (9) | 0.0044 (6) | 0.0122 (7) | 0.0058 (7) |
| C4 | 0.0296 (8) | 0.0351 (9) | 0.0376 (9) | 0.0098 (7) | 0.0137 (7) | 0.0131 (7) |
| C5 | 0.0259 (8) | 0.0441 (10) | 0.0322 (9) | 0.0078 (7) | 0.0076 (7) | 0.0114 (7) |
| C6 | 0.0241 (8) | 0.0376 (9) | 0.0304 (8) | 0.0039 (7) | 0.0068 (6) | 0.0043 (7) |
| C7 | 0.0217 (7) | 0.0332 (8) | 0.0281 (8) | 0.0035 (6) | 0.0088 (6) | 0.0043 (6) |
| C8 | 0.0192 (7) | 0.0302 (8) | 0.0278 (8) | 0.0009 (6) | 0.0066 (6) | 0.0031 (6) |
| C9 | 0.0200 (7) | 0.0275 (8) | 0.0276 (8) | −0.0018 (6) | 0.0039 (6) | 0.0028 (6) |
| C10 | 0.0236 (7) | 0.0252 (8) | 0.0290 (8) | −0.0017 (6) | 0.0052 (6) | 0.0043 (6) |
| C11 | 0.0259 (8) | 0.0292 (8) | 0.0308 (8) | −0.0038 (6) | 0.0019 (6) | 0.0025 (7) |
| C12 | 0.0332 (8) | 0.0297 (8) | 0.0284 (8) | −0.0039 (7) | 0.0068 (7) | −0.0012 (6) |
| C13 | 0.0314 (8) | 0.0288 (8) | 0.0340 (9) | 0.0018 (6) | 0.0097 (7) | −0.0012 (7) |
| C14 | 0.0260 (8) | 0.0291 (8) | 0.0307 (8) | 0.0025 (6) | 0.0049 (6) | 0.0036 (6) |
| C15 | 0.0245 (7) | 0.0240 (7) | 0.0265 (8) | 0.0001 (6) | 0.0043 (6) | 0.0037 (6) |
| C16 | 0.0219 (7) | 0.0261 (8) | 0.0252 (8) | 0.0031 (6) | 0.0043 (6) | 0.0053 (6) |
| C17 | 0.0224 (7) | 0.0269 (8) | 0.0224 (7) | 0.0039 (6) | 0.0034 (6) | 0.0020 (6) |
| C18 | 0.0242 (7) | 0.0294 (8) | 0.0207 (7) | 0.0014 (6) | 0.0036 (6) | −0.0007 (6) |
| C19 | 0.0243 (8) | 0.0339 (9) | 0.0242 (8) | 0.0025 (6) | 0.0046 (6) | −0.0025 (6) |
| C20 | 0.0226 (7) | 0.0409 (9) | 0.0284 (8) | −0.0022 (7) | 0.0067 (6) | −0.0046 (7) |
| C21 | 0.0292 (8) | 0.0350 (9) | 0.0292 (8) | −0.0062 (7) | 0.0074 (7) | −0.0030 (7) |
| C22 | 0.0303 (8) | 0.0290 (8) | 0.0271 (8) | −0.0002 (6) | 0.0069 (6) | −0.0009 (6) |
| C23 | 0.0249 (7) | 0.0295 (8) | 0.0218 (7) | 0.0007 (6) | 0.0050 (6) | −0.0008 (6) |
| C24 | 0.0249 (7) | 0.0261 (8) | 0.0241 (7) | 0.0016 (6) | 0.0067 (6) | −0.0008 (6) |
| C25 | 0.0297 (8) | 0.0415 (9) | 0.0301 (9) | 0.0015 (7) | 0.0034 (7) | 0.0041 (7) |
| C26 | 0.0434 (10) | 0.0456 (10) | 0.0333 (9) | 0.0007 (8) | 0.0105 (8) | 0.0046 (8) |
| B1 | 0.0201 (8) | 0.0270 (9) | 0.0270 (9) | 0.0022 (7) | 0.0046 (7) | 0.0028 (7) |
Geometric parameters (Å, º) top
| O1—B1 | 1.418 (2) | C10—C11 | 1.391 (2) |
| O1—C25 | 1.4257 (19) | C10—C15 | 1.428 (2) |
| N1—C8 | 1.3628 (19) | C11—C12 | 1.380 (2) |
| N1—C1 | 1.363 (2) | C11—H11A | 0.9500 |
| N1—B1 | 1.496 (2) | C12—C13 | 1.397 (2) |
| N2—C8 | 1.344 (2) | C12—H12A | 0.9500 |
| N2—C9 | 1.3491 (19) | C13—C14 | 1.384 (2) |
| N3—C16 | 1.3694 (18) | C13—H13A | 0.9500 |
| N3—C9 | 1.3700 (19) | C14—C15 | 1.390 (2) |
| N3—B1 | 1.507 (2) | C14—H14A | 0.9500 |
| N4—C17 | 1.3456 (19) | C15—C16 | 1.451 (2) |
| N4—C16 | 1.3460 (19) | C17—C18 | 1.452 (2) |
| N5—C24 | 1.368 (2) | C18—C19 | 1.397 (2) |
| N5—C17 | 1.3691 (18) | C18—C23 | 1.423 (2) |
| N5—B1 | 1.507 (2) | C19—C20 | 1.379 (2) |
| N6—C1 | 1.3466 (19) | C19—H19A | 0.9500 |
| N6—C24 | 1.3520 (19) | C20—C21 | 1.398 (2) |
| C1—C2 | 1.463 (2) | C20—H20A | 0.9500 |
| C2—C3 | 1.389 (2) | C21—C22 | 1.387 (2) |
| C2—C7 | 1.423 (2) | C21—H21A | 0.9500 |
| C3—C4 | 1.390 (2) | C22—C23 | 1.396 (2) |
| C3—H3A | 0.9500 | C22—H22A | 0.9500 |
| C4—C5 | 1.400 (3) | C23—C24 | 1.459 (2) |
| C4—H4A | 0.9500 | C25—C26 | 1.504 (2) |
| C5—C6 | 1.386 (2) | C25—H25A | 0.9900 |
| C5—H5A | 0.9500 | C25—H25B | 0.9900 |
| C6—C7 | 1.400 (2) | C26—H26A | 0.9800 |
| C6—H6A | 0.9500 | C26—H26B | 0.9800 |
| C7—C8 | 1.458 (2) | C26—H26C | 0.9800 |
| C9—C10 | 1.456 (2) | ||
| B1—O1—C25 | 119.65 (11) | C13—C14—C15 | 118.14 (14) |
| C8—N1—C1 | 113.82 (12) | C13—C14—H14A | 120.9 |
| C8—N1—B1 | 123.23 (13) | C15—C14—H14A | 120.9 |
| C1—N1—B1 | 122.84 (13) | C14—C15—C10 | 120.55 (14) |
| C8—N2—C9 | 116.65 (13) | C14—C15—C16 | 132.06 (14) |
| C16—N3—C9 | 112.81 (12) | C10—C15—C16 | 107.00 (13) |
| C16—N3—B1 | 123.39 (12) | N4—C16—N3 | 122.59 (13) |
| C9—N3—B1 | 122.37 (12) | N4—C16—C15 | 129.18 (13) |
| C17—N4—C16 | 116.87 (12) | N3—C16—C15 | 106.08 (12) |
| C24—N5—C17 | 112.87 (12) | N4—C17—N5 | 122.77 (13) |
| C24—N5—B1 | 122.33 (12) | N4—C17—C18 | 129.38 (13) |
| C17—N5—B1 | 123.32 (13) | N5—C17—C18 | 105.91 (12) |
| C1—N6—C24 | 116.79 (13) | C19—C18—C23 | 120.73 (14) |
| N6—C1—N1 | 122.06 (13) | C19—C18—C17 | 131.86 (14) |
| N6—C1—C2 | 131.62 (14) | C23—C18—C17 | 107.26 (12) |
| N1—C1—C2 | 105.21 (13) | C20—C19—C18 | 117.76 (14) |
| C3—C2—C7 | 120.86 (14) | C20—C19—H19A | 121.1 |
| C3—C2—C1 | 132.21 (15) | C18—C19—H19A | 121.1 |
| C7—C2—C1 | 106.94 (13) | C19—C20—C21 | 121.82 (14) |
| C2—C3—C4 | 117.87 (15) | C19—C20—H20A | 119.1 |
| C2—C3—H3A | 121.1 | C21—C20—H20A | 119.1 |
| C4—C3—H3A | 121.1 | C22—C21—C20 | 121.28 (15) |
| C3—C4—C5 | 121.49 (15) | C22—C21—H21A | 119.4 |
| C3—C4—H4A | 119.3 | C20—C21—H21A | 119.4 |
| C5—C4—H4A | 119.3 | C21—C22—C23 | 117.89 (14) |
| C6—C5—C4 | 121.28 (15) | C21—C22—H22A | 121.1 |
| C6—C5—H5A | 119.4 | C23—C22—H22A | 121.1 |
| C4—C5—H5A | 119.4 | C22—C23—C18 | 120.49 (14) |
| C5—C6—C7 | 117.95 (16) | C22—C23—C24 | 132.34 (14) |
| C5—C6—H6A | 121.0 | C18—C23—C24 | 107.02 (13) |
| C7—C6—H6A | 121.0 | N6—C24—N5 | 122.86 (13) |
| C6—C7—C2 | 120.47 (14) | N6—C24—C23 | 129.87 (14) |
| C6—C7—C8 | 132.19 (15) | N5—C24—C23 | 105.71 (12) |
| C2—C7—C8 | 107.33 (13) | O1—C25—C26 | 108.53 (13) |
| N2—C8—N1 | 121.90 (13) | O1—C25—H25A | 110.0 |
| N2—C8—C7 | 131.66 (14) | C26—C25—H25A | 110.0 |
| N1—C8—C7 | 105.24 (13) | O1—C25—H25B | 110.0 |
| N2—C9—N3 | 123.08 (13) | C26—C25—H25B | 110.0 |
| N2—C9—C10 | 129.55 (14) | H25A—C25—H25B | 108.4 |
| N3—C9—C10 | 105.82 (12) | C25—C26—H26A | 109.5 |
| C11—C10—C15 | 120.18 (14) | C25—C26—H26B | 109.5 |
| C11—C10—C9 | 132.17 (14) | H26A—C26—H26B | 109.5 |
| C15—C10—C9 | 107.17 (13) | C25—C26—H26C | 109.5 |
| C12—C11—C10 | 118.38 (14) | H26A—C26—H26C | 109.5 |
| C12—C11—H11A | 120.8 | H26B—C26—H26C | 109.5 |
| C10—C11—H11A | 120.8 | O1—B1—N1 | 110.46 (12) |
| C11—C12—C13 | 121.31 (15) | O1—B1—N5 | 118.17 (13) |
| C11—C12—H12A | 119.3 | N1—B1—N5 | 103.20 (12) |
| C13—C12—H12A | 119.3 | O1—B1—N3 | 117.11 (13) |
| C14—C13—C12 | 121.33 (15) | N1—B1—N3 | 102.83 (12) |
| C14—C13—H13A | 119.3 | N5—B1—N3 | 103.16 (12) |
| C12—C13—H13A | 119.3 | ||
| C24—N6—C1—N1 | −6.0 (2) | C14—C15—C16—N4 | −16.8 (3) |
| C24—N6—C1—C2 | 160.12 (15) | C10—C15—C16—N4 | 155.77 (14) |
| C8—N1—C1—N6 | 156.80 (13) | C14—C15—C16—N3 | 179.82 (15) |
| B1—N1—C1—N6 | −19.5 (2) | C10—C15—C16—N3 | −7.59 (16) |
| C8—N1—C1—C2 | −12.45 (16) | C16—N4—C17—N5 | −9.1 (2) |
| B1—N1—C1—C2 | 171.22 (13) | C16—N4—C17—C18 | 152.72 (15) |
| N6—C1—C2—C3 | 19.3 (3) | C24—N5—C17—N4 | 154.15 (13) |
| N1—C1—C2—C3 | −172.91 (15) | B1—N5—C17—N4 | −12.2 (2) |
| N6—C1—C2—C7 | −160.49 (15) | C24—N5—C17—C18 | −11.34 (16) |
| N1—C1—C2—C7 | 7.31 (15) | B1—N5—C17—C18 | −177.72 (13) |
| C7—C2—C3—C4 | −1.6 (2) | N4—C17—C18—C19 | 17.9 (3) |
| C1—C2—C3—C4 | 178.61 (15) | N5—C17—C18—C19 | −177.93 (15) |
| C2—C3—C4—C5 | 2.6 (2) | N4—C17—C18—C23 | −157.53 (14) |
| C3—C4—C5—C6 | −0.9 (2) | N5—C17—C18—C23 | 6.65 (16) |
| C4—C5—C6—C7 | −1.7 (2) | C23—C18—C19—C20 | −1.4 (2) |
| C5—C6—C7—C2 | 2.6 (2) | C17—C18—C19—C20 | −176.29 (15) |
| C5—C6—C7—C8 | −178.40 (15) | C18—C19—C20—C21 | 1.6 (2) |
| C3—C2—C7—C6 | −0.9 (2) | C19—C20—C21—C22 | −0.2 (2) |
| C1—C2—C7—C6 | 178.88 (13) | C20—C21—C22—C23 | −1.3 (2) |
| C3—C2—C7—C8 | 179.82 (13) | C21—C22—C23—C18 | 1.5 (2) |
| C1—C2—C7—C8 | −0.37 (16) | C21—C22—C23—C24 | 176.41 (15) |
| C9—N2—C8—N1 | 6.3 (2) | C19—C18—C23—C22 | −0.2 (2) |
| C9—N2—C8—C7 | −159.23 (15) | C17—C18—C23—C22 | 175.85 (13) |
| C1—N1—C8—N2 | −156.59 (13) | C19—C18—C23—C24 | −176.23 (13) |
| B1—N1—C8—N2 | 19.7 (2) | C17—C18—C23—C24 | −0.19 (16) |
| C1—N1—C8—C7 | 12.23 (16) | C1—N6—C24—N5 | 10.1 (2) |
| B1—N1—C8—C7 | −171.46 (13) | C1—N6—C24—C23 | −153.51 (15) |
| C6—C7—C8—N2 | −18.6 (3) | C17—N5—C24—N6 | −155.84 (13) |
| C2—C7—C8—N2 | 160.55 (15) | B1—N5—C24—N6 | 10.7 (2) |
| C6—C7—C8—N1 | 174.17 (15) | C17—N5—C24—C23 | 11.19 (16) |
| C2—C7—C8—N1 | −6.71 (16) | B1—N5—C24—C23 | 177.73 (13) |
| C8—N2—C9—N3 | −10.9 (2) | C22—C23—C24—N6 | −15.9 (3) |
| C8—N2—C9—C10 | 152.75 (15) | C18—C23—C24—N6 | 159.45 (15) |
| C16—N3—C9—N2 | 156.91 (14) | C22—C23—C24—N5 | 178.28 (15) |
| B1—N3—C9—N2 | −9.9 (2) | C18—C23—C24—N5 | −6.33 (16) |
| C16—N3—C9—C10 | −10.08 (16) | B1—O1—C25—C26 | 175.74 (14) |
| B1—N3—C9—C10 | −176.86 (12) | C25—O1—B1—N1 | 161.12 (13) |
| N2—C9—C10—C11 | 10.6 (3) | C25—O1—B1—N5 | 42.67 (19) |
| N3—C9—C10—C11 | 176.44 (15) | C25—O1—B1—N3 | −81.67 (17) |
| N2—C9—C10—C15 | −161.15 (15) | C8—N1—B1—O1 | 91.19 (16) |
| N3—C9—C10—C15 | 4.69 (16) | C1—N1—B1—O1 | −92.82 (16) |
| C15—C10—C11—C12 | −3.4 (2) | C8—N1—B1—N5 | −141.58 (13) |
| C9—C10—C11—C12 | −174.31 (15) | C1—N1—B1—N5 | 34.41 (18) |
| C10—C11—C12—C13 | 1.4 (2) | C8—N1—B1—N3 | −34.53 (17) |
| C11—C12—C13—C14 | 1.7 (2) | C1—N1—B1—N3 | 141.46 (13) |
| C12—C13—C14—C15 | −2.7 (2) | C24—N5—B1—O1 | 92.26 (17) |
| C13—C14—C15—C10 | 0.6 (2) | C17—N5—B1—O1 | −102.61 (16) |
| C13—C14—C15—C16 | 172.42 (15) | C24—N5—B1—N1 | −29.94 (18) |
| C11—C10—C15—C14 | 2.5 (2) | C17—N5—B1—N1 | 135.19 (13) |
| C9—C10—C15—C14 | 175.39 (13) | C24—N5—B1—N3 | −136.74 (13) |
| C11—C10—C15—C16 | −171.16 (13) | C17—N5—B1—N3 | 28.39 (18) |
| C9—C10—C15—C16 | 1.77 (16) | C16—N3—B1—O1 | 102.80 (16) |
| C17—N4—C16—N3 | 8.7 (2) | C9—N3—B1—O1 | −91.83 (17) |
| C17—N4—C16—C15 | −152.26 (15) | C16—N3—B1—N1 | −135.91 (13) |
| C9—N3—C16—N4 | −153.51 (14) | C9—N3—B1—N1 | 29.45 (17) |
| B1—N3—C16—N4 | 13.1 (2) | C16—N3—B1—N5 | −28.83 (18) |
| C9—N3—C16—C15 | 11.22 (16) | C9—N3—B1—N5 | 136.53 (13) |
| B1—N3—C16—C15 | 177.83 (13) |
(Subphthalocyaninato)(2,2,2-trifluoroethanolato)boron (d22126_a) top
Crystal data top
| C26H14BF3N6O | F(000) = 1008 |
| Mr = 494.24 | Dx = 1.506 Mg m−3 |
| Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
| a = 10.4664 (6) Å | Cell parameters from 8597 reflections |
| b = 15.4986 (8) Å | θ = 4.4–65.2° |
| c = 14.3171 (8) Å | µ = 0.96 mm−1 |
| β = 110.221 (3)° | T = 150 K |
| V = 2179.3 (2) Å3 | Needle, purple |
| Z = 4 | 0.14 × 0.09 × 0.04 mm |
Data collection top
| Bruker Kappa APEX-DUO CMOS PHOTON II diffractometer | 3043 reflections with I > 2σ(I) |
| Radiation source: Incoatec ImuS with multi-layer optics | Rint = 0.083 |
| φ and ω scans | θmax = 66.3°, θmin = 4.4° |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −12→12 |
| Tmin = 0.624, Tmax = 0.753 | k = −18→18 |
| 39716 measured reflections | l = −16→16 |
| 3759 independent reflections |
Refinement top
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.039 | w = 1/[σ2(Fo2) + (0.0593P)2 + 0.5694P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.107 | (Δ/σ)max < 0.001 |
| S = 1.04 | Δρmax = 0.27 e Å−3 |
| 3759 reflections | Δρmin = −0.28 e Å−3 |
| 335 parameters | Extinction correction: SHELXL2019 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| 0 restraints | Extinction coefficient: 0.0077 (6) |
| Primary atom site location: structure-invariant direct methods |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| F1 | 0.14828 (12) | 0.32579 (9) | 0.15721 (11) | 0.0619 (4) | |
| F2 | 0.12876 (12) | 0.35980 (8) | 0.00694 (10) | 0.0642 (4) | |
| F3 | 0.10380 (11) | 0.22880 (7) | 0.04406 (9) | 0.0493 (3) | |
| O1 | 0.40052 (12) | 0.36016 (7) | 0.13347 (8) | 0.0281 (3) | |
| N1 | 0.60948 (13) | 0.42611 (8) | 0.23935 (10) | 0.0240 (3) | |
| N2 | 0.53157 (13) | 0.55917 (9) | 0.28127 (10) | 0.0253 (3) | |
| N3 | 0.42606 (13) | 0.42704 (8) | 0.29839 (10) | 0.0236 (3) | |
| N4 | 0.39573 (13) | 0.30705 (9) | 0.39199 (10) | 0.0249 (3) | |
| N5 | 0.54216 (13) | 0.29777 (9) | 0.29696 (10) | 0.0238 (3) | |
| N6 | 0.75795 (14) | 0.30516 (9) | 0.27647 (10) | 0.0267 (3) | |
| C1 | 0.73096 (16) | 0.38769 (11) | 0.24857 (11) | 0.0247 (4) | |
| C2 | 0.82193 (17) | 0.45773 (11) | 0.24592 (12) | 0.0261 (4) | |
| C3 | 0.95492 (17) | 0.45794 (12) | 0.24534 (13) | 0.0299 (4) | |
| H3A | 1.002880 | 0.405582 | 0.247105 | 0.036* | |
| C4 | 1.01423 (19) | 0.53653 (12) | 0.24214 (14) | 0.0337 (4) | |
| H4A | 1.104046 | 0.538081 | 0.240258 | 0.040* | |
| C5 | 0.94627 (18) | 0.61398 (12) | 0.24159 (13) | 0.0339 (4) | |
| H5A | 0.990399 | 0.667082 | 0.239219 | 0.041* | |
| C6 | 0.81507 (18) | 0.61465 (11) | 0.24444 (12) | 0.0303 (4) | |
| H6A | 0.769392 | 0.667474 | 0.245174 | 0.036* | |
| C7 | 0.75239 (17) | 0.53604 (11) | 0.24620 (12) | 0.0258 (4) | |
| C8 | 0.61905 (16) | 0.51318 (10) | 0.25096 (11) | 0.0240 (4) | |
| C9 | 0.44168 (16) | 0.51425 (10) | 0.31008 (11) | 0.0239 (4) | |
| C10 | 0.36737 (16) | 0.53890 (11) | 0.37553 (12) | 0.0254 (4) | |
| C11 | 0.33740 (17) | 0.61856 (11) | 0.40721 (12) | 0.0291 (4) | |
| H11A | 0.368751 | 0.670501 | 0.387225 | 0.035* | |
| C12 | 0.26033 (18) | 0.62009 (12) | 0.46888 (13) | 0.0325 (4) | |
| H12A | 0.235136 | 0.673985 | 0.488973 | 0.039* | |
| C13 | 0.21908 (18) | 0.54373 (12) | 0.50201 (13) | 0.0322 (4) | |
| H13A | 0.166915 | 0.546880 | 0.544601 | 0.039* | |
| C14 | 0.25226 (17) | 0.46388 (11) | 0.47436 (12) | 0.0285 (4) | |
| H14A | 0.226622 | 0.412318 | 0.499143 | 0.034* | |
| C15 | 0.32478 (16) | 0.46125 (11) | 0.40874 (12) | 0.0252 (4) | |
| C16 | 0.37397 (16) | 0.39014 (11) | 0.36432 (12) | 0.0243 (4) | |
| C17 | 0.48759 (16) | 0.26371 (11) | 0.36294 (11) | 0.0244 (4) | |
| C18 | 0.57039 (17) | 0.18891 (10) | 0.40590 (12) | 0.0248 (4) | |
| C19 | 0.56054 (18) | 0.12527 (11) | 0.47146 (12) | 0.0287 (4) | |
| H19A | 0.486998 | 0.124697 | 0.495976 | 0.034* | |
| C20 | 0.66076 (19) | 0.06292 (11) | 0.49991 (12) | 0.0320 (4) | |
| H20A | 0.653186 | 0.017315 | 0.542023 | 0.038* | |
| C21 | 0.77307 (19) | 0.06506 (11) | 0.46843 (13) | 0.0342 (4) | |
| H21A | 0.841187 | 0.021796 | 0.490708 | 0.041* | |
| C22 | 0.78658 (18) | 0.12919 (11) | 0.40537 (13) | 0.0301 (4) | |
| H22A | 0.864497 | 0.131765 | 0.385839 | 0.036* | |
| C23 | 0.68316 (17) | 0.18960 (10) | 0.37145 (12) | 0.0256 (4) | |
| C24 | 0.66641 (16) | 0.26342 (10) | 0.30644 (12) | 0.0248 (4) | |
| C25 | 0.32578 (17) | 0.28402 (11) | 0.10139 (13) | 0.0285 (4) | |
| H25A | 0.356760 | 0.239782 | 0.154346 | 0.034* | |
| H25B | 0.342072 | 0.261682 | 0.041700 | 0.034* | |
| C26 | 0.17718 (19) | 0.30021 (12) | 0.07709 (14) | 0.0354 (4) | |
| B1 | 0.48581 (19) | 0.37544 (12) | 0.23485 (13) | 0.0237 (4) |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| F1 | 0.0388 (7) | 0.0799 (9) | 0.0757 (9) | −0.0018 (6) | 0.0309 (6) | −0.0268 (7) |
| F2 | 0.0441 (7) | 0.0473 (7) | 0.0741 (9) | −0.0030 (6) | −0.0144 (6) | 0.0187 (6) |
| F3 | 0.0363 (6) | 0.0454 (7) | 0.0586 (7) | −0.0149 (5) | 0.0067 (5) | −0.0029 (6) |
| O1 | 0.0299 (6) | 0.0294 (6) | 0.0235 (6) | −0.0066 (5) | 0.0071 (5) | 0.0005 (5) |
| N1 | 0.0236 (7) | 0.0262 (7) | 0.0229 (7) | −0.0005 (5) | 0.0089 (6) | 0.0004 (5) |
| N2 | 0.0240 (7) | 0.0275 (7) | 0.0233 (7) | 0.0005 (6) | 0.0068 (6) | 0.0031 (6) |
| N3 | 0.0204 (7) | 0.0264 (7) | 0.0231 (7) | 0.0006 (5) | 0.0066 (6) | 0.0020 (6) |
| N4 | 0.0230 (7) | 0.0279 (7) | 0.0239 (7) | −0.0006 (6) | 0.0083 (6) | −0.0001 (6) |
| N5 | 0.0239 (7) | 0.0247 (7) | 0.0240 (7) | −0.0008 (5) | 0.0096 (6) | −0.0006 (6) |
| N6 | 0.0280 (8) | 0.0283 (7) | 0.0255 (7) | 0.0002 (6) | 0.0114 (6) | −0.0008 (6) |
| C1 | 0.0257 (9) | 0.0282 (9) | 0.0213 (8) | 0.0006 (7) | 0.0094 (7) | −0.0013 (7) |
| C2 | 0.0258 (9) | 0.0327 (9) | 0.0196 (8) | −0.0014 (7) | 0.0077 (7) | 0.0012 (7) |
| C3 | 0.0246 (9) | 0.0384 (10) | 0.0269 (9) | 0.0021 (7) | 0.0093 (7) | 0.0048 (7) |
| C4 | 0.0242 (9) | 0.0448 (11) | 0.0313 (9) | −0.0038 (8) | 0.0086 (7) | 0.0057 (8) |
| C5 | 0.0295 (10) | 0.0373 (10) | 0.0339 (9) | −0.0088 (7) | 0.0098 (8) | 0.0052 (8) |
| C6 | 0.0311 (9) | 0.0305 (9) | 0.0284 (9) | −0.0025 (7) | 0.0091 (7) | 0.0014 (7) |
| C7 | 0.0252 (9) | 0.0306 (9) | 0.0216 (8) | −0.0017 (7) | 0.0080 (7) | 0.0001 (7) |
| C8 | 0.0240 (8) | 0.0262 (8) | 0.0205 (8) | −0.0006 (7) | 0.0061 (7) | 0.0022 (6) |
| C9 | 0.0223 (8) | 0.0264 (8) | 0.0219 (8) | 0.0011 (6) | 0.0062 (7) | 0.0019 (7) |
| C10 | 0.0204 (8) | 0.0306 (9) | 0.0225 (8) | 0.0013 (6) | 0.0039 (7) | −0.0005 (7) |
| C11 | 0.0271 (9) | 0.0300 (9) | 0.0273 (9) | −0.0001 (7) | 0.0057 (7) | −0.0012 (7) |
| C12 | 0.0332 (10) | 0.0345 (10) | 0.0280 (9) | 0.0026 (7) | 0.0085 (8) | −0.0065 (7) |
| C13 | 0.0300 (9) | 0.0428 (11) | 0.0242 (9) | 0.0038 (8) | 0.0099 (7) | −0.0029 (7) |
| C14 | 0.0274 (9) | 0.0341 (9) | 0.0242 (8) | 0.0015 (7) | 0.0091 (7) | 0.0021 (7) |
| C15 | 0.0207 (8) | 0.0309 (9) | 0.0223 (8) | 0.0018 (6) | 0.0052 (7) | 0.0007 (7) |
| C16 | 0.0214 (8) | 0.0285 (9) | 0.0222 (8) | −0.0023 (6) | 0.0064 (7) | 0.0017 (7) |
| C17 | 0.0238 (8) | 0.0271 (8) | 0.0222 (8) | −0.0037 (7) | 0.0076 (7) | −0.0011 (7) |
| C18 | 0.0290 (9) | 0.0226 (8) | 0.0224 (8) | −0.0033 (7) | 0.0083 (7) | −0.0029 (6) |
| C19 | 0.0349 (9) | 0.0267 (9) | 0.0245 (8) | −0.0042 (7) | 0.0104 (7) | −0.0032 (7) |
| C20 | 0.0433 (11) | 0.0259 (9) | 0.0257 (9) | −0.0015 (8) | 0.0105 (8) | 0.0014 (7) |
| C21 | 0.0390 (10) | 0.0284 (9) | 0.0325 (9) | 0.0049 (8) | 0.0088 (8) | −0.0001 (8) |
| C22 | 0.0311 (9) | 0.0292 (9) | 0.0295 (9) | 0.0013 (7) | 0.0099 (7) | −0.0036 (7) |
| C23 | 0.0290 (9) | 0.0252 (8) | 0.0225 (8) | −0.0009 (7) | 0.0090 (7) | −0.0040 (6) |
| C24 | 0.0255 (9) | 0.0263 (8) | 0.0241 (8) | −0.0005 (7) | 0.0103 (7) | −0.0028 (7) |
| C25 | 0.0311 (9) | 0.0282 (9) | 0.0272 (8) | −0.0034 (7) | 0.0114 (7) | −0.0041 (7) |
| C26 | 0.0326 (10) | 0.0325 (10) | 0.0378 (10) | −0.0037 (8) | 0.0081 (8) | −0.0031 (8) |
| B1 | 0.0223 (9) | 0.0266 (10) | 0.0233 (9) | −0.0015 (7) | 0.0092 (8) | 0.0004 (7) |
Geometric parameters (Å, º) top
| F1—C26 | 1.343 (2) | C6—H6A | 0.9500 |
| F2—C26 | 1.329 (2) | C7—C8 | 1.464 (2) |
| F3—C26 | 1.337 (2) | C9—C10 | 1.461 (2) |
| O1—C25 | 1.403 (2) | C10—C11 | 1.388 (2) |
| O1—B1 | 1.437 (2) | C10—C15 | 1.421 (2) |
| N1—C8 | 1.359 (2) | C11—C12 | 1.387 (3) |
| N1—C1 | 1.368 (2) | C11—H11A | 0.9500 |
| N1—B1 | 1.496 (2) | C12—C13 | 1.398 (3) |
| N2—C9 | 1.345 (2) | C12—H12A | 0.9500 |
| N2—C8 | 1.345 (2) | C13—C14 | 1.380 (3) |
| N3—C9 | 1.365 (2) | C13—H13A | 0.9500 |
| N3—C16 | 1.368 (2) | C14—C15 | 1.398 (2) |
| N3—B1 | 1.500 (2) | C14—H14A | 0.9500 |
| N4—C16 | 1.343 (2) | C15—C16 | 1.453 (2) |
| N4—C17 | 1.351 (2) | C17—C18 | 1.451 (2) |
| N5—C17 | 1.367 (2) | C18—C19 | 1.390 (2) |
| N5—C24 | 1.368 (2) | C18—C23 | 1.428 (2) |
| N5—B1 | 1.492 (2) | C19—C20 | 1.380 (3) |
| N6—C1 | 1.341 (2) | C19—H19A | 0.9500 |
| N6—C24 | 1.343 (2) | C20—C21 | 1.397 (3) |
| C1—C2 | 1.453 (2) | C20—H20A | 0.9500 |
| C2—C3 | 1.395 (3) | C21—C22 | 1.382 (3) |
| C2—C7 | 1.416 (2) | C21—H21A | 0.9500 |
| C3—C4 | 1.375 (2) | C22—C23 | 1.386 (2) |
| C3—H3A | 0.9500 | C22—H22A | 0.9500 |
| C4—C5 | 1.394 (3) | C23—C24 | 1.447 (2) |
| C4—H4A | 0.9500 | C25—C26 | 1.493 (3) |
| C5—C6 | 1.388 (3) | C25—H25A | 0.9900 |
| C5—H5A | 0.9500 | C25—H25B | 0.9900 |
| C6—C7 | 1.388 (2) | ||
| C25—O1—B1 | 123.44 (13) | C13—C14—C15 | 117.91 (16) |
| C8—N1—C1 | 113.17 (13) | C13—C14—H14A | 121.0 |
| C8—N1—B1 | 123.54 (14) | C15—C14—H14A | 121.0 |
| C1—N1—B1 | 122.48 (14) | C14—C15—C10 | 120.41 (15) |
| C9—N2—C8 | 116.80 (14) | C14—C15—C16 | 132.33 (16) |
| C9—N3—C16 | 112.89 (13) | C10—C15—C16 | 107.25 (14) |
| C9—N3—B1 | 123.02 (14) | N4—C16—N3 | 122.48 (15) |
| C16—N3—B1 | 122.99 (14) | N4—C16—C15 | 130.37 (15) |
| C16—N4—C17 | 116.86 (14) | N3—C16—C15 | 105.72 (14) |
| C17—N5—C24 | 113.02 (13) | N4—C17—N5 | 122.17 (14) |
| C17—N5—B1 | 123.35 (14) | N4—C17—C18 | 130.62 (15) |
| C24—N5—B1 | 122.66 (13) | N5—C17—C18 | 105.69 (14) |
| C1—N6—C24 | 117.03 (14) | C19—C18—C23 | 120.12 (15) |
| N6—C1—N1 | 122.48 (15) | C19—C18—C17 | 132.90 (16) |
| N6—C1—C2 | 130.39 (15) | C23—C18—C17 | 106.94 (14) |
| N1—C1—C2 | 105.53 (14) | C20—C19—C18 | 118.04 (17) |
| C3—C2—C7 | 120.86 (15) | C20—C19—H19A | 121.0 |
| C3—C2—C1 | 131.77 (16) | C18—C19—H19A | 121.0 |
| C7—C2—C1 | 107.35 (14) | C19—C20—C21 | 121.77 (17) |
| C4—C3—C2 | 117.73 (16) | C19—C20—H20A | 119.1 |
| C4—C3—H3A | 121.1 | C21—C20—H20A | 119.1 |
| C2—C3—H3A | 121.1 | C22—C21—C20 | 121.00 (17) |
| C3—C4—C5 | 121.85 (17) | C22—C21—H21A | 119.5 |
| C3—C4—H4A | 119.1 | C20—C21—H21A | 119.5 |
| C5—C4—H4A | 119.1 | C21—C22—C23 | 118.08 (17) |
| C6—C5—C4 | 120.95 (17) | C21—C22—H22A | 121.0 |
| C6—C5—H5A | 119.5 | C23—C22—H22A | 121.0 |
| C4—C5—H5A | 119.5 | C22—C23—C18 | 120.83 (16) |
| C7—C6—C5 | 118.21 (17) | C22—C23—C24 | 131.76 (16) |
| C7—C6—H6A | 120.9 | C18—C23—C24 | 107.30 (14) |
| C5—C6—H6A | 120.9 | N6—C24—N5 | 122.65 (14) |
| C6—C7—C2 | 120.38 (16) | N6—C24—C23 | 130.17 (15) |
| C6—C7—C8 | 132.64 (16) | N5—C24—C23 | 105.74 (14) |
| C2—C7—C8 | 106.97 (14) | O1—C25—C26 | 110.68 (14) |
| N2—C8—N1 | 122.41 (14) | O1—C25—H25A | 109.5 |
| N2—C8—C7 | 130.75 (15) | C26—C25—H25A | 109.5 |
| N1—C8—C7 | 105.41 (14) | O1—C25—H25B | 109.5 |
| N2—C9—N3 | 122.82 (15) | C26—C25—H25B | 109.5 |
| N2—C9—C10 | 130.21 (15) | H25A—C25—H25B | 108.1 |
| N3—C9—C10 | 105.66 (14) | F2—C26—F3 | 106.60 (14) |
| C11—C10—C15 | 120.77 (16) | F2—C26—F1 | 107.49 (16) |
| C11—C10—C9 | 132.30 (16) | F3—C26—F1 | 105.96 (16) |
| C15—C10—C9 | 106.93 (14) | F2—C26—C25 | 112.78 (16) |
| C12—C11—C10 | 118.04 (16) | F3—C26—C25 | 111.61 (15) |
| C12—C11—H11A | 121.0 | F1—C26—C25 | 111.99 (15) |
| C10—C11—H11A | 121.0 | O1—B1—N5 | 116.67 (14) |
| C11—C12—C13 | 121.16 (16) | O1—B1—N1 | 110.87 (14) |
| C11—C12—H12A | 119.4 | N5—B1—N1 | 103.88 (13) |
| C13—C12—H12A | 119.4 | O1—B1—N3 | 117.18 (14) |
| C14—C13—C12 | 121.61 (17) | N5—B1—N3 | 103.33 (13) |
| C14—C13—H13A | 119.2 | N1—B1—N3 | 103.28 (13) |
| C12—C13—H13A | 119.2 | ||
| C24—N6—C1—N1 | −7.4 (2) | C10—C15—C16—N4 | 158.64 (16) |
| C24—N6—C1—C2 | 155.98 (16) | C14—C15—C16—N3 | 174.03 (17) |
| C8—N1—C1—N6 | 154.59 (15) | C10—C15—C16—N3 | −7.64 (17) |
| B1—N1—C1—N6 | −15.4 (2) | C16—N4—C17—N5 | −9.1 (2) |
| C8—N1—C1—C2 | −12.37 (17) | C16—N4—C17—C18 | 154.73 (16) |
| B1—N1—C1—C2 | 177.64 (14) | C24—N5—C17—N4 | 155.36 (14) |
| N6—C1—C2—C3 | 19.4 (3) | B1—N5—C17—N4 | −13.6 (2) |
| N1—C1—C2—C3 | −175.05 (17) | C24—N5—C17—C18 | −11.96 (17) |
| N6—C1—C2—C7 | −159.14 (16) | B1—N5—C17—C18 | 179.06 (14) |
| N1—C1—C2—C7 | 6.39 (17) | N4—C17—C18—C19 | 19.2 (3) |
| C7—C2—C3—C4 | −1.8 (2) | N5—C17—C18—C19 | −174.95 (17) |
| C1—C2—C3—C4 | 179.75 (17) | N4—C17—C18—C23 | −158.20 (16) |
| C2—C3—C4—C5 | 1.3 (3) | N5—C17—C18—C23 | 7.64 (17) |
| C3—C4—C5—C6 | 0.1 (3) | C23—C18—C19—C20 | −1.2 (2) |
| C4—C5—C6—C7 | −1.1 (3) | C17—C18—C19—C20 | −178.37 (16) |
| C5—C6—C7—C2 | 0.5 (2) | C18—C19—C20—C21 | 3.1 (2) |
| C5—C6—C7—C8 | 178.76 (17) | C19—C20—C21—C22 | −1.4 (3) |
| C3—C2—C7—C6 | 0.9 (2) | C20—C21—C22—C23 | −2.2 (3) |
| C1—C2—C7—C6 | 179.70 (15) | C21—C22—C23—C18 | 4.1 (2) |
| C3—C2—C7—C8 | −177.70 (15) | C21—C22—C23—C24 | 179.74 (16) |
| C1—C2—C7—C8 | 1.05 (17) | C19—C18—C23—C22 | −2.4 (2) |
| C9—N2—C8—N1 | 6.9 (2) | C17—C18—C23—C22 | 175.42 (15) |
| C9—N2—C8—C7 | −157.45 (16) | C19—C18—C23—C24 | −179.02 (14) |
| C1—N1—C8—N2 | −154.74 (14) | C17—C18—C23—C24 | −1.21 (17) |
| B1—N1—C8—N2 | 15.1 (2) | C1—N6—C24—N5 | 8.8 (2) |
| C1—N1—C8—C7 | 12.99 (17) | C1—N6—C24—C23 | −155.46 (16) |
| B1—N1—C8—C7 | −177.14 (14) | C17—N5—C24—N6 | −156.34 (15) |
| C6—C7—C8—N2 | −20.3 (3) | B1—N5—C24—N6 | 12.7 (2) |
| C2—C7—C8—N2 | 158.15 (16) | C17—N5—C24—C23 | 11.21 (17) |
| C6—C7—C8—N1 | 173.44 (17) | B1—N5—C24—C23 | −179.72 (14) |
| C2—C7—C8—N1 | −8.15 (17) | C22—C23—C24—N6 | −15.5 (3) |
| C8—N2—C9—N3 | −8.0 (2) | C18—C23—C24—N6 | 160.58 (16) |
| C8—N2—C9—C10 | 156.98 (16) | C22—C23—C24—N5 | 178.20 (17) |
| C16—N3—C9—N2 | 155.65 (14) | C18—C23—C24—N5 | −5.68 (17) |
| B1—N3—C9—N2 | −12.6 (2) | B1—O1—C25—C26 | 108.42 (17) |
| C16—N3—C9—C10 | −12.50 (17) | O1—C25—C26—F2 | 58.5 (2) |
| B1—N3—C9—C10 | 179.23 (13) | O1—C25—C26—F3 | 178.51 (14) |
| N2—C9—C10—C11 | 19.1 (3) | O1—C25—C26—F1 | −62.88 (19) |
| N3—C9—C10—C11 | −173.93 (17) | C25—O1—B1—N5 | 26.0 (2) |
| N2—C9—C10—C15 | −160.02 (16) | C25—O1—B1—N1 | 144.61 (14) |
| N3—C9—C10—C15 | 6.91 (16) | C25—O1—B1—N3 | −97.22 (18) |
| C15—C10—C11—C12 | −2.5 (2) | C17—N5—B1—O1 | −99.68 (18) |
| C9—C10—C11—C12 | 178.46 (16) | C24—N5—B1—O1 | 92.39 (18) |
| C10—C11—C12—C13 | 2.9 (3) | C17—N5—B1—N1 | 137.99 (14) |
| C11—C12—C13—C14 | −0.5 (3) | C24—N5—B1—N1 | −29.94 (19) |
| C12—C13—C14—C15 | −2.3 (3) | C17—N5—B1—N3 | 30.43 (19) |
| C13—C14—C15—C10 | 2.6 (2) | C24—N5—B1—N3 | −137.50 (14) |
| C13—C14—C15—C16 | −179.22 (16) | C8—N1—B1—O1 | 96.21 (18) |
| C11—C10—C15—C14 | −0.3 (2) | C1—N1—B1—O1 | −94.85 (17) |
| C9—C10—C15—C14 | 179.02 (14) | C8—N1—B1—N5 | −137.70 (14) |
| C11—C10—C15—C16 | −178.82 (14) | C1—N1—B1—N5 | 31.24 (19) |
| C9—C10—C15—C16 | 0.46 (17) | C8—N1—B1—N3 | −30.11 (19) |
| C17—N4—C16—N3 | 9.1 (2) | C1—N1—B1—N3 | 138.84 (14) |
| C17—N4—C16—C15 | −155.18 (16) | C9—N3—B1—O1 | −93.42 (18) |
| C9—N3—C16—N4 | −154.83 (14) | C16—N3—B1—O1 | 99.48 (17) |
| B1—N3—C16—N4 | 13.4 (2) | C9—N3—B1—N5 | 136.78 (14) |
| C9—N3—C16—C15 | 12.79 (17) | C16—N3—B1—N5 | −30.32 (19) |
| B1—N3—C16—C15 | −178.93 (13) | C9—N3—B1—N1 | 28.76 (19) |
| C14—C15—C16—N4 | −19.7 (3) | C16—N3—B1—N1 | −138.34 (14) |
(Butanolato)(subphthalocyaninato)boron (d2365_a) top
Crystal data top
| C28H21BN6O | Dx = 1.354 Mg m−3 |
| Mr = 468.32 | Cu Kα radiation, λ = 1.54178 Å |
| Orthorhombic, Pbca | Cell parameters from 7196 reflections |
| a = 14.6398 (8) Å | θ = 4.7–63.5° |
| b = 15.2842 (9) Å | µ = 0.68 mm−1 |
| c = 20.5313 (12) Å | T = 150 K |
| V = 4594.0 (5) Å3 | Shard, red |
| Z = 8 | 0.15 × 0.07 × 0.06 mm |
| F(000) = 1952 |
Data collection top
| Bruker Kappa APEX-DUO CMOS PHOTON II diffractometer | 3295 reflections with I > 2σ(I) |
| Radiation source: Incoatec ImuS with multi-layer optics | Rint = 0.065 |
| φ and ω scans | θmax = 66.3°, θmin = 4.7° |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −17→16 |
| Tmin = 0.661, Tmax = 0.753 | k = −16→17 |
| 45733 measured reflections | l = −24→24 |
| 3951 independent reflections |
Refinement top
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
| wR(F2) = 0.095 | w = 1/[σ2(Fo2) + (0.0386P)2 + 1.7934P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.07 | (Δ/σ)max = 0.001 |
| 3951 reflections | Δρmax = 0.33 e Å−3 |
| 326 parameters | Δρmin = −0.22 e Å−3 |
| 0 restraints |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.65454 (7) | 0.16749 (7) | 0.52754 (5) | 0.0285 (3) | |
| N1 | 0.58690 (8) | 0.22126 (8) | 0.42800 (6) | 0.0248 (3) | |
| N2 | 0.44187 (9) | 0.26949 (8) | 0.46684 (6) | 0.0263 (3) | |
| N3 | 0.57903 (9) | 0.31323 (8) | 0.51964 (6) | 0.0250 (3) | |
| N4 | 0.70172 (8) | 0.41129 (8) | 0.54038 (6) | 0.0267 (3) | |
| N5 | 0.71948 (8) | 0.29367 (8) | 0.46566 (6) | 0.0252 (3) | |
| N6 | 0.71634 (9) | 0.23507 (8) | 0.35842 (6) | 0.0275 (3) | |
| C1 | 0.62896 (10) | 0.21061 (10) | 0.36922 (7) | 0.0259 (3) | |
| C2 | 0.55680 (11) | 0.19102 (10) | 0.32311 (7) | 0.0269 (3) | |
| C3 | 0.55809 (11) | 0.17229 (10) | 0.25676 (8) | 0.0322 (4) | |
| H3A | 0.614156 | 0.167151 | 0.233781 | 0.039* | |
| C4 | 0.47546 (12) | 0.16141 (11) | 0.22530 (8) | 0.0363 (4) | |
| H4A | 0.475089 | 0.147802 | 0.180154 | 0.044* | |
| C5 | 0.39223 (12) | 0.16993 (11) | 0.25832 (8) | 0.0342 (4) | |
| H5A | 0.336628 | 0.162068 | 0.235187 | 0.041* | |
| C6 | 0.38963 (11) | 0.18955 (10) | 0.32386 (8) | 0.0300 (4) | |
| H6A | 0.333032 | 0.195459 | 0.346052 | 0.036* | |
| C7 | 0.47213 (11) | 0.20048 (10) | 0.35668 (7) | 0.0263 (3) | |
| C8 | 0.49379 (10) | 0.22703 (10) | 0.42291 (7) | 0.0253 (3) | |
| C9 | 0.48618 (10) | 0.31643 (10) | 0.51220 (7) | 0.0251 (3) | |
| C10 | 0.45570 (10) | 0.39165 (10) | 0.55014 (7) | 0.0264 (3) | |
| C11 | 0.36938 (11) | 0.42489 (11) | 0.56440 (7) | 0.0303 (4) | |
| H11A | 0.315704 | 0.397116 | 0.548633 | 0.036* | |
| C12 | 0.36428 (12) | 0.49964 (11) | 0.60225 (8) | 0.0343 (4) | |
| H12A | 0.306052 | 0.521543 | 0.614558 | 0.041* | |
| C13 | 0.44299 (12) | 0.54373 (11) | 0.62283 (8) | 0.0343 (4) | |
| H13A | 0.436989 | 0.595398 | 0.648198 | 0.041* | |
| C14 | 0.52909 (11) | 0.51372 (10) | 0.60704 (8) | 0.0306 (4) | |
| H14A | 0.582202 | 0.545163 | 0.619654 | 0.037* | |
| C15 | 0.53575 (10) | 0.43579 (10) | 0.57201 (7) | 0.0260 (3) | |
| C16 | 0.61408 (11) | 0.38657 (10) | 0.54796 (7) | 0.0257 (3) | |
| C17 | 0.75094 (10) | 0.36772 (10) | 0.49558 (7) | 0.0256 (3) | |
| C18 | 0.82841 (10) | 0.39771 (10) | 0.45701 (8) | 0.0270 (4) | |
| C19 | 0.88477 (11) | 0.47080 (10) | 0.46284 (8) | 0.0304 (4) | |
| H19A | 0.881078 | 0.508072 | 0.499773 | 0.036* | |
| C20 | 0.94620 (11) | 0.48738 (11) | 0.41319 (9) | 0.0355 (4) | |
| H20A | 0.986726 | 0.535668 | 0.416917 | 0.043* | |
| C21 | 0.94995 (11) | 0.43464 (12) | 0.35767 (9) | 0.0372 (4) | |
| H21A | 0.992352 | 0.448279 | 0.324149 | 0.045* | |
| C22 | 0.89308 (11) | 0.36290 (11) | 0.35053 (8) | 0.0327 (4) | |
| H22A | 0.895339 | 0.327776 | 0.312391 | 0.039* | |
| C23 | 0.83258 (10) | 0.34367 (10) | 0.40074 (8) | 0.0275 (3) | |
| C24 | 0.75772 (10) | 0.28113 (10) | 0.40558 (7) | 0.0264 (3) | |
| C25 | 0.69849 (13) | 0.18122 (11) | 0.58877 (8) | 0.0371 (4) | |
| H25A | 0.663075 | 0.223900 | 0.614799 | 0.045* | |
| H25B | 0.760334 | 0.205582 | 0.581576 | 0.045* | |
| C26 | 0.70553 (11) | 0.09683 (11) | 0.62503 (8) | 0.0327 (4) | |
| H26A | 0.742726 | 0.055377 | 0.599157 | 0.039* | |
| H26B | 0.643656 | 0.071458 | 0.629674 | 0.039* | |
| C27 | 0.74800 (13) | 0.10629 (12) | 0.69235 (8) | 0.0405 (4) | |
| H27A | 0.810516 | 0.130236 | 0.687871 | 0.049* | |
| H27B | 0.711594 | 0.148443 | 0.718175 | 0.049* | |
| C28 | 0.75238 (17) | 0.02032 (14) | 0.72826 (10) | 0.0595 (6) | |
| H28A | 0.785888 | 0.028192 | 0.769166 | 0.089* | |
| H28B | 0.783825 | −0.023103 | 0.701230 | 0.089* | |
| H28C | 0.690291 | 0.000015 | 0.737717 | 0.089* | |
| B1 | 0.63728 (12) | 0.24284 (11) | 0.48926 (8) | 0.0254 (4) |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0352 (6) | 0.0240 (6) | 0.0262 (6) | −0.0006 (5) | −0.0076 (5) | −0.0007 (4) |
| N1 | 0.0262 (7) | 0.0232 (7) | 0.0248 (7) | 0.0000 (5) | −0.0014 (5) | −0.0011 (5) |
| N2 | 0.0288 (7) | 0.0253 (7) | 0.0248 (7) | −0.0025 (5) | −0.0003 (5) | 0.0021 (5) |
| N3 | 0.0276 (7) | 0.0243 (7) | 0.0232 (6) | −0.0011 (5) | −0.0012 (5) | −0.0007 (5) |
| N4 | 0.0278 (7) | 0.0262 (7) | 0.0261 (7) | 0.0006 (5) | −0.0029 (5) | −0.0013 (5) |
| N5 | 0.0256 (7) | 0.0243 (7) | 0.0257 (7) | 0.0013 (5) | −0.0017 (5) | −0.0016 (5) |
| N6 | 0.0268 (7) | 0.0255 (7) | 0.0302 (7) | 0.0020 (5) | −0.0003 (5) | −0.0036 (6) |
| C1 | 0.0290 (8) | 0.0231 (8) | 0.0258 (8) | 0.0028 (6) | 0.0003 (6) | −0.0016 (6) |
| C2 | 0.0318 (9) | 0.0214 (8) | 0.0274 (8) | 0.0016 (6) | −0.0027 (7) | −0.0021 (6) |
| C3 | 0.0372 (9) | 0.0301 (9) | 0.0292 (8) | 0.0032 (7) | 0.0015 (7) | −0.0052 (7) |
| C4 | 0.0449 (10) | 0.0371 (10) | 0.0268 (8) | 0.0045 (8) | −0.0070 (8) | −0.0073 (7) |
| C5 | 0.0372 (9) | 0.0320 (9) | 0.0334 (9) | 0.0013 (7) | −0.0102 (7) | −0.0046 (7) |
| C6 | 0.0302 (9) | 0.0275 (8) | 0.0323 (9) | 0.0006 (7) | −0.0041 (7) | −0.0024 (7) |
| C7 | 0.0302 (8) | 0.0213 (8) | 0.0275 (8) | 0.0007 (6) | −0.0022 (6) | −0.0007 (6) |
| C8 | 0.0266 (8) | 0.0234 (8) | 0.0260 (8) | −0.0010 (6) | −0.0011 (6) | 0.0014 (6) |
| C9 | 0.0263 (8) | 0.0257 (8) | 0.0233 (8) | −0.0017 (6) | 0.0007 (6) | 0.0032 (6) |
| C10 | 0.0318 (8) | 0.0272 (8) | 0.0202 (7) | 0.0014 (7) | 0.0011 (6) | 0.0035 (6) |
| C11 | 0.0313 (9) | 0.0335 (9) | 0.0261 (8) | 0.0029 (7) | 0.0004 (7) | 0.0049 (7) |
| C12 | 0.0364 (9) | 0.0364 (9) | 0.0301 (9) | 0.0108 (7) | 0.0038 (7) | 0.0041 (7) |
| C13 | 0.0444 (10) | 0.0286 (9) | 0.0299 (9) | 0.0070 (7) | 0.0021 (7) | −0.0011 (7) |
| C14 | 0.0376 (9) | 0.0273 (8) | 0.0269 (8) | 0.0012 (7) | 0.0001 (7) | −0.0003 (7) |
| C15 | 0.0306 (8) | 0.0251 (8) | 0.0222 (8) | 0.0008 (6) | 0.0017 (6) | 0.0031 (6) |
| C16 | 0.0312 (8) | 0.0238 (8) | 0.0222 (8) | −0.0008 (6) | −0.0021 (6) | 0.0003 (6) |
| C17 | 0.0274 (8) | 0.0234 (8) | 0.0261 (8) | 0.0005 (6) | −0.0053 (7) | −0.0019 (6) |
| C18 | 0.0235 (8) | 0.0249 (8) | 0.0327 (9) | 0.0035 (6) | −0.0035 (6) | 0.0003 (7) |
| C19 | 0.0276 (8) | 0.0270 (8) | 0.0364 (9) | 0.0004 (6) | −0.0040 (7) | −0.0005 (7) |
| C20 | 0.0294 (9) | 0.0327 (9) | 0.0445 (10) | −0.0035 (7) | −0.0032 (8) | 0.0038 (8) |
| C21 | 0.0279 (9) | 0.0421 (10) | 0.0416 (10) | −0.0018 (7) | 0.0031 (7) | 0.0050 (8) |
| C22 | 0.0272 (9) | 0.0361 (9) | 0.0348 (9) | 0.0035 (7) | 0.0019 (7) | −0.0021 (7) |
| C23 | 0.0240 (8) | 0.0257 (8) | 0.0330 (8) | 0.0038 (6) | −0.0016 (6) | 0.0000 (7) |
| C24 | 0.0258 (8) | 0.0247 (8) | 0.0287 (8) | 0.0046 (6) | −0.0004 (7) | −0.0019 (7) |
| C25 | 0.0501 (11) | 0.0324 (9) | 0.0288 (9) | 0.0005 (8) | −0.0114 (8) | −0.0004 (7) |
| C26 | 0.0339 (9) | 0.0319 (9) | 0.0325 (9) | −0.0025 (7) | −0.0037 (7) | 0.0028 (7) |
| C27 | 0.0484 (11) | 0.0415 (10) | 0.0318 (9) | −0.0047 (8) | −0.0061 (8) | 0.0034 (8) |
| C28 | 0.0765 (15) | 0.0565 (13) | 0.0457 (12) | −0.0175 (11) | −0.0181 (11) | 0.0175 (10) |
| B1 | 0.0277 (9) | 0.0244 (9) | 0.0241 (9) | −0.0005 (7) | −0.0010 (7) | −0.0020 (7) |
Geometric parameters (Å, º) top
| O1—B1 | 1.417 (2) | C11—H11A | 0.9500 |
| O1—C25 | 1.4277 (19) | C12—C13 | 1.400 (2) |
| N1—C1 | 1.3646 (19) | C12—H12A | 0.9500 |
| N1—C8 | 1.3700 (19) | C13—C14 | 1.380 (2) |
| N1—B1 | 1.495 (2) | C13—H13A | 0.9500 |
| N2—C9 | 1.343 (2) | C14—C15 | 1.395 (2) |
| N2—C8 | 1.346 (2) | C14—H14A | 0.9500 |
| N3—C16 | 1.3630 (19) | C15—C16 | 1.458 (2) |
| N3—C9 | 1.369 (2) | C17—C18 | 1.457 (2) |
| N3—B1 | 1.508 (2) | C18—C19 | 1.394 (2) |
| N4—C17 | 1.345 (2) | C18—C23 | 1.421 (2) |
| N4—C16 | 1.346 (2) | C19—C20 | 1.383 (2) |
| N5—C17 | 1.3676 (19) | C19—H19A | 0.9500 |
| N5—C24 | 1.3680 (19) | C20—C21 | 1.397 (3) |
| N5—B1 | 1.512 (2) | C20—H20A | 0.9500 |
| N6—C24 | 1.342 (2) | C21—C22 | 1.385 (2) |
| N6—C1 | 1.351 (2) | C21—H21A | 0.9500 |
| C1—C2 | 1.450 (2) | C22—C23 | 1.391 (2) |
| C2—C3 | 1.392 (2) | C22—H22A | 0.9500 |
| C2—C7 | 1.426 (2) | C23—C24 | 1.458 (2) |
| C3—C4 | 1.381 (2) | C25—C26 | 1.493 (2) |
| C3—H3A | 0.9500 | C25—H25A | 0.9900 |
| C4—C5 | 1.401 (2) | C25—H25B | 0.9900 |
| C4—H4A | 0.9500 | C26—C27 | 1.523 (2) |
| C5—C6 | 1.379 (2) | C26—H26A | 0.9900 |
| C5—H5A | 0.9500 | C26—H26B | 0.9900 |
| C6—C7 | 1.393 (2) | C27—C28 | 1.508 (3) |
| C6—H6A | 0.9500 | C27—H27A | 0.9900 |
| C7—C8 | 1.454 (2) | C27—H27B | 0.9900 |
| C9—C10 | 1.459 (2) | C28—H28A | 0.9800 |
| C10—C11 | 1.393 (2) | C28—H28B | 0.9800 |
| C10—C15 | 1.425 (2) | C28—H28C | 0.9800 |
| C11—C12 | 1.384 (2) | ||
| B1—O1—C25 | 116.69 (12) | N4—C16—N3 | 122.69 (14) |
| C1—N1—C8 | 112.90 (12) | N4—C16—C15 | 130.09 (14) |
| C1—N1—B1 | 123.22 (13) | N3—C16—C15 | 105.83 (13) |
| C8—N1—B1 | 122.74 (13) | N4—C17—N5 | 122.45 (14) |
| C9—N2—C8 | 116.71 (13) | N4—C17—C18 | 129.27 (14) |
| C16—N3—C9 | 113.09 (13) | N5—C17—C18 | 106.15 (13) |
| C16—N3—B1 | 123.39 (13) | C19—C18—C23 | 120.67 (15) |
| C9—N3—B1 | 122.74 (13) | C19—C18—C17 | 131.76 (15) |
| C17—N4—C16 | 116.79 (13) | C23—C18—C17 | 106.99 (13) |
| C17—N5—C24 | 112.53 (13) | C20—C19—C18 | 117.94 (15) |
| C17—N5—B1 | 123.31 (12) | C20—C19—H19A | 121.0 |
| C24—N5—B1 | 122.86 (12) | C18—C19—H19A | 121.0 |
| C24—N6—C1 | 117.02 (13) | C19—C20—C21 | 121.41 (16) |
| N6—C1—N1 | 122.64 (14) | C19—C20—H20A | 119.3 |
| N6—C1—C2 | 129.79 (14) | C21—C20—H20A | 119.3 |
| N1—C1—C2 | 105.86 (13) | C22—C21—C20 | 121.31 (16) |
| C3—C2—C7 | 120.38 (14) | C22—C21—H21A | 119.3 |
| C3—C2—C1 | 132.19 (15) | C20—C21—H21A | 119.3 |
| C7—C2—C1 | 107.27 (13) | C21—C22—C23 | 118.16 (15) |
| C4—C3—C2 | 118.07 (15) | C21—C22—H22A | 120.9 |
| C4—C3—H3A | 121.0 | C23—C22—H22A | 120.9 |
| C2—C3—H3A | 121.0 | C22—C23—C18 | 120.46 (14) |
| C3—C4—C5 | 121.63 (15) | C22—C23—C24 | 131.92 (15) |
| C3—C4—H4A | 119.2 | C18—C23—C24 | 107.07 (13) |
| C5—C4—H4A | 119.2 | N6—C24—N5 | 122.65 (14) |
| C6—C5—C4 | 121.09 (15) | N6—C24—C23 | 129.38 (14) |
| C6—C5—H5A | 119.5 | N5—C24—C23 | 106.09 (13) |
| C4—C5—H5A | 119.5 | O1—C25—C26 | 110.07 (13) |
| C5—C6—C7 | 118.31 (15) | O1—C25—H25A | 109.6 |
| C5—C6—H6A | 120.8 | C26—C25—H25A | 109.6 |
| C7—C6—H6A | 120.8 | O1—C25—H25B | 109.6 |
| C6—C7—C2 | 120.51 (14) | C26—C25—H25B | 109.6 |
| C6—C7—C8 | 132.45 (15) | H25A—C25—H25B | 108.2 |
| C2—C7—C8 | 106.90 (13) | C25—C26—C27 | 113.51 (14) |
| N2—C8—N1 | 122.80 (13) | C25—C26—H26A | 108.9 |
| N2—C8—C7 | 129.64 (14) | C27—C26—H26A | 108.9 |
| N1—C8—C7 | 105.69 (13) | C25—C26—H26B | 108.9 |
| N2—C9—N3 | 122.56 (14) | C27—C26—H26B | 108.9 |
| N2—C9—C10 | 130.07 (14) | H26A—C26—H26B | 107.7 |
| N3—C9—C10 | 105.80 (13) | C28—C27—C26 | 112.24 (15) |
| C11—C10—C15 | 120.48 (14) | C28—C27—H27A | 109.2 |
| C11—C10—C9 | 132.62 (15) | C26—C27—H27A | 109.2 |
| C15—C10—C9 | 106.85 (13) | C28—C27—H27B | 109.2 |
| C12—C11—C10 | 117.91 (15) | C26—C27—H27B | 109.2 |
| C12—C11—H11A | 121.0 | H27A—C27—H27B | 107.9 |
| C10—C11—H11A | 121.0 | C27—C28—H28A | 109.5 |
| C11—C12—C13 | 121.50 (15) | C27—C28—H28B | 109.5 |
| C11—C12—H12A | 119.3 | H28A—C28—H28B | 109.5 |
| C13—C12—H12A | 119.3 | C27—C28—H28C | 109.5 |
| C14—C13—C12 | 121.39 (15) | H28A—C28—H28C | 109.5 |
| C14—C13—H13A | 119.3 | H28B—C28—H28C | 109.5 |
| C12—C13—H13A | 119.3 | O1—B1—N1 | 112.04 (13) |
| C13—C14—C15 | 117.95 (15) | O1—B1—N3 | 116.83 (13) |
| C13—C14—H14A | 121.0 | N1—B1—N3 | 103.09 (12) |
| C15—C14—H14A | 121.0 | O1—B1—N5 | 116.97 (13) |
| C14—C15—C10 | 120.62 (14) | N1—B1—N5 | 103.67 (12) |
| C14—C15—C16 | 132.09 (14) | N3—B1—N5 | 102.47 (12) |
| C10—C15—C16 | 107.22 (13) | ||
| C24—N6—C1—N1 | −8.4 (2) | C10—C15—C16—N4 | 160.67 (15) |
| C24—N6—C1—C2 | 154.51 (15) | C14—C15—C16—N3 | 177.24 (15) |
| C8—N1—C1—N6 | 154.80 (14) | C10—C15—C16—N3 | −5.86 (16) |
| B1—N1—C1—N6 | −13.3 (2) | C16—N4—C17—N5 | −9.5 (2) |
| C8—N1—C1—C2 | −11.62 (16) | C16—N4—C17—C18 | 151.51 (15) |
| B1—N1—C1—C2 | −179.71 (13) | C24—N5—C17—N4 | 153.85 (14) |
| N6—C1—C2—C3 | 16.4 (3) | B1—N5—C17—N4 | −13.5 (2) |
| N1—C1—C2—C3 | −178.53 (16) | C24—N5—C17—C18 | −10.97 (16) |
| N6—C1—C2—C7 | −158.88 (15) | B1—N5—C17—C18 | −178.28 (13) |
| N1—C1—C2—C7 | 6.20 (16) | N4—C17—C18—C19 | 14.1 (3) |
| C7—C2—C3—C4 | −1.4 (2) | N5—C17—C18—C19 | 177.53 (16) |
| C1—C2—C3—C4 | −176.16 (16) | N4—C17—C18—C23 | −157.01 (15) |
| C2—C3—C4—C5 | 0.9 (2) | N5—C17—C18—C23 | 6.41 (16) |
| C3—C4—C5—C6 | −0.1 (3) | C23—C18—C19—C20 | −1.8 (2) |
| C4—C5—C6—C7 | −0.2 (2) | C17—C18—C19—C20 | −171.89 (16) |
| C5—C6—C7—C2 | −0.3 (2) | C18—C19—C20—C21 | 2.2 (2) |
| C5—C6—C7—C8 | 174.89 (16) | C19—C20—C21—C22 | −0.9 (3) |
| C3—C2—C7—C6 | 1.2 (2) | C20—C21—C22—C23 | −0.9 (2) |
| C1—C2—C7—C6 | 177.11 (14) | C21—C22—C23—C18 | 1.3 (2) |
| C3—C2—C7—C8 | −175.16 (14) | C21—C22—C23—C24 | 171.58 (16) |
| C1—C2—C7—C8 | 0.78 (16) | C19—C18—C23—C22 | 0.0 (2) |
| C9—N2—C8—N1 | 8.5 (2) | C17—C18—C23—C22 | 172.32 (14) |
| C9—N2—C8—C7 | −153.64 (15) | C19—C18—C23—C24 | −172.41 (14) |
| C1—N1—C8—N2 | −153.67 (14) | C17—C18—C23—C24 | −0.10 (16) |
| B1—N1—C8—N2 | 14.5 (2) | C1—N6—C24—N5 | 8.6 (2) |
| C1—N1—C8—C7 | 12.10 (17) | C1—N6—C24—C23 | −153.51 (15) |
| B1—N1—C8—C7 | −179.74 (13) | C17—N5—C24—N6 | −154.79 (14) |
| C6—C7—C8—N2 | −18.7 (3) | B1—N5—C24—N6 | 12.6 (2) |
| C2—C7—C8—N2 | 156.99 (15) | C17—N5—C24—C23 | 10.90 (16) |
| C6—C7—C8—N1 | 176.85 (16) | B1—N5—C24—C23 | 178.27 (13) |
| C2—C7—C8—N1 | −7.44 (16) | C22—C23—C24—N6 | −13.1 (3) |
| C8—N2—C9—N3 | −8.3 (2) | C18—C23—C24—N6 | 158.15 (15) |
| C8—N2—C9—C10 | 155.31 (15) | C22—C23—C24—N5 | −177.46 (16) |
| C16—N3—C9—N2 | 155.60 (14) | C18—C23—C24—N5 | −6.24 (16) |
| B1—N3—C9—N2 | −14.6 (2) | B1—O1—C25—C26 | 175.87 (14) |
| C16—N3—C9—C10 | −11.42 (17) | O1—C25—C26—C27 | −177.48 (14) |
| B1—N3—C9—C10 | 178.37 (13) | C25—C26—C27—C28 | 178.82 (17) |
| N2—C9—C10—C11 | 18.6 (3) | C25—O1—B1—N1 | −177.06 (13) |
| N3—C9—C10—C11 | −175.67 (16) | C25—O1—B1—N3 | −58.47 (19) |
| N2—C9—C10—C15 | −158.69 (15) | C25—O1—B1—N5 | 63.47 (18) |
| N3—C9—C10—C15 | 6.99 (16) | C1—N1—B1—O1 | −97.97 (16) |
| C15—C10—C11—C12 | −2.4 (2) | C8—N1—B1—O1 | 95.08 (17) |
| C9—C10—C11—C12 | −179.44 (15) | C1—N1—B1—N3 | 135.58 (14) |
| C10—C11—C12—C13 | 3.5 (2) | C8—N1—B1—N3 | −31.36 (18) |
| C11—C12—C13—C14 | −1.0 (2) | C1—N1—B1—N5 | 29.03 (18) |
| C12—C13—C14—C15 | −2.5 (2) | C8—N1—B1—N5 | −137.91 (13) |
| C13—C14—C15—C10 | 3.5 (2) | C16—N3—B1—O1 | 98.99 (17) |
| C13—C14—C15—C16 | −179.89 (16) | C9—N3—B1—O1 | −91.81 (17) |
| C11—C10—C15—C14 | −1.1 (2) | C16—N3—B1—N1 | −137.69 (13) |
| C9—C10—C15—C14 | 176.62 (13) | C9—N3—B1—N1 | 31.50 (18) |
| C11—C10—C15—C16 | −178.43 (14) | C16—N3—B1—N5 | −30.24 (18) |
| C9—C10—C15—C16 | −0.71 (16) | C9—N3—B1—N5 | 138.96 (14) |
| C17—N4—C16—N3 | 9.7 (2) | C17—N5—B1—O1 | −98.84 (17) |
| C17—N4—C16—C15 | −154.90 (15) | C24—N5—B1—O1 | 95.14 (17) |
| C9—N3—C16—N4 | −156.81 (14) | C17—N5—B1—N1 | 137.31 (13) |
| B1—N3—C16—N4 | 13.3 (2) | C24—N5—B1—N1 | −28.71 (18) |
| C9—N3—C16—C15 | 10.97 (17) | C17—N5—B1—N3 | 30.30 (18) |
| B1—N3—C16—C15 | −178.90 (13) | C24—N5—B1—N3 | −135.72 (13) |
| C14—C15—C16—N4 | −16.2 (3) |
(tert-Butanolato)(subphthalocyaninato)boron (d23115_a) top
Crystal data top
| C28H21BN6O | F(000) = 976 |
| Mr = 468.32 | Dx = 1.346 Mg m−3 |
| Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
| a = 14.3815 (7) Å | Cell parameters from 9907 reflections |
| b = 8.2702 (4) Å | θ = 3.1–65.6° |
| c = 19.8660 (9) Å | µ = 0.68 mm−1 |
| β = 102.074 (2)° | T = 150 K |
| V = 2310.55 (19) Å3 | Shard, pink |
| Z = 4 | 0.17 × 0.09 × 0.02 mm |
Data collection top
| Bruker Kappa APEX-DUO CMOS PHOTON II diffractometer | 3363 reflections with I > 2σ(I) |
| Radiation source: Incoatec ImuS with multi-layer optics | Rint = 0.052 |
| φ and ω scans | θmax = 66.4°, θmin = 3.1° |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −17→16 |
| Tmin = 0.673, Tmax = 0.753 | k = −9→9 |
| 41764 measured reflections | l = −23→23 |
| 3994 independent reflections |
Refinement top
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.035 | w = 1/[σ2(Fo2) + (0.043P)2 + 0.6555P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.089 | (Δ/σ)max < 0.001 |
| S = 1.05 | Δρmax = 0.22 e Å−3 |
| 3994 reflections | Δρmin = −0.17 e Å−3 |
| 329 parameters | Extinction correction: SHELXL2019 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| 0 restraints | Extinction coefficient: 0.0027 (2) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.13233 (7) | 0.45659 (12) | 0.34123 (5) | 0.0322 (2) | |
| N1 | 0.25586 (8) | 0.26134 (13) | 0.35481 (6) | 0.0257 (3) | |
| N2 | 0.38286 (8) | 0.42521 (14) | 0.33597 (6) | 0.0273 (3) | |
| N3 | 0.29197 (8) | 0.50116 (14) | 0.41822 (6) | 0.0261 (3) | |
| N4 | 0.26678 (8) | 0.50795 (14) | 0.53271 (6) | 0.0282 (3) | |
| N5 | 0.19298 (8) | 0.30535 (14) | 0.45350 (6) | 0.0269 (3) | |
| N6 | 0.18897 (8) | 0.04134 (15) | 0.40441 (6) | 0.0295 (3) | |
| C1 | 0.23293 (10) | 0.10185 (17) | 0.35669 (7) | 0.0264 (3) | |
| C2 | 0.28511 (10) | 0.02031 (17) | 0.31120 (7) | 0.0269 (3) | |
| C3 | 0.28641 (11) | −0.13979 (18) | 0.28963 (7) | 0.0313 (3) | |
| H3A | 0.246279 | −0.218727 | 0.303556 | 0.038* | |
| C4 | 0.34791 (11) | −0.18023 (19) | 0.24732 (8) | 0.0358 (4) | |
| H4A | 0.348608 | −0.287988 | 0.230871 | 0.043* | |
| C5 | 0.40911 (11) | −0.06566 (19) | 0.22827 (8) | 0.0347 (4) | |
| H5A | 0.450767 | −0.097125 | 0.199282 | 0.042* | |
| C6 | 0.41009 (10) | 0.09253 (18) | 0.25084 (7) | 0.0301 (3) | |
| H6A | 0.453337 | 0.168813 | 0.238916 | 0.036* | |
| C7 | 0.34651 (10) | 0.13761 (17) | 0.29132 (7) | 0.0263 (3) | |
| C8 | 0.32972 (10) | 0.28996 (17) | 0.32361 (7) | 0.0253 (3) | |
| C9 | 0.36722 (10) | 0.52164 (16) | 0.38687 (7) | 0.0264 (3) | |
| C10 | 0.43102 (10) | 0.63519 (16) | 0.42978 (7) | 0.0277 (3) | |
| C11 | 0.51788 (10) | 0.70194 (17) | 0.42372 (8) | 0.0314 (3) | |
| H11A | 0.544142 | 0.680471 | 0.384550 | 0.038* | |
| C12 | 0.56482 (11) | 0.80038 (17) | 0.47634 (8) | 0.0337 (3) | |
| H12A | 0.623371 | 0.849009 | 0.472596 | 0.040* | |
| C13 | 0.52780 (11) | 0.82968 (17) | 0.53489 (8) | 0.0335 (4) | |
| H13A | 0.561216 | 0.898917 | 0.569887 | 0.040* | |
| C14 | 0.44356 (11) | 0.75980 (17) | 0.54275 (8) | 0.0313 (3) | |
| H14A | 0.419707 | 0.777328 | 0.583280 | 0.038* | |
| C15 | 0.39448 (10) | 0.66299 (16) | 0.48975 (7) | 0.0283 (3) | |
| C16 | 0.30911 (10) | 0.56455 (16) | 0.48327 (7) | 0.0272 (3) | |
| C17 | 0.21516 (10) | 0.37185 (17) | 0.51812 (7) | 0.0275 (3) | |
| C18 | 0.19411 (10) | 0.24788 (18) | 0.56463 (7) | 0.0282 (3) | |
| C19 | 0.20229 (10) | 0.24625 (19) | 0.63576 (7) | 0.0315 (3) | |
| H19A | 0.220049 | 0.340896 | 0.662455 | 0.038* | |
| C20 | 0.18385 (11) | 0.1032 (2) | 0.66637 (8) | 0.0376 (4) | |
| H20A | 0.186793 | 0.100649 | 0.714580 | 0.045* | |
| C21 | 0.16091 (12) | −0.0380 (2) | 0.62762 (8) | 0.0423 (4) | |
| H21A | 0.149430 | −0.134835 | 0.650270 | 0.051* | |
| C22 | 0.15452 (12) | −0.0400 (2) | 0.55722 (8) | 0.0383 (4) | |
| H22A | 0.140249 | −0.136935 | 0.531472 | 0.046* | |
| C23 | 0.16970 (10) | 0.10470 (18) | 0.52524 (7) | 0.0305 (3) | |
| C24 | 0.17644 (10) | 0.14261 (17) | 0.45474 (7) | 0.0281 (3) | |
| C25 | 0.04743 (10) | 0.53426 (18) | 0.35279 (8) | 0.0307 (3) | |
| C26 | 0.00330 (13) | 0.6075 (2) | 0.28332 (9) | 0.0488 (4) | |
| H26A | −0.056878 | 0.660087 | 0.286012 | 0.073* | |
| H26B | −0.008593 | 0.522026 | 0.248406 | 0.073* | |
| H26C | 0.046902 | 0.687616 | 0.270735 | 0.073* | |
| C27 | 0.07026 (11) | 0.66450 (19) | 0.40753 (9) | 0.0396 (4) | |
| H27A | 0.011984 | 0.723032 | 0.410430 | 0.059* | |
| H27B | 0.116618 | 0.740102 | 0.395416 | 0.059* | |
| H27C | 0.096944 | 0.614488 | 0.452109 | 0.059* | |
| C28 | −0.01812 (11) | 0.4078 (2) | 0.37321 (9) | 0.0433 (4) | |
| H28A | −0.080008 | 0.456834 | 0.373695 | 0.065* | |
| H28B | 0.009899 | 0.366219 | 0.419177 | 0.065* | |
| H28C | −0.026529 | 0.318737 | 0.339947 | 0.065* | |
| B1 | 0.20919 (11) | 0.3904 (2) | 0.38962 (8) | 0.0270 (4) |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0296 (5) | 0.0411 (6) | 0.0274 (5) | 0.0076 (4) | 0.0091 (4) | 0.0016 (4) |
| N1 | 0.0276 (6) | 0.0273 (6) | 0.0234 (6) | 0.0002 (5) | 0.0083 (5) | −0.0003 (5) |
| N2 | 0.0309 (6) | 0.0273 (6) | 0.0249 (6) | 0.0010 (5) | 0.0085 (5) | 0.0025 (5) |
| N3 | 0.0294 (6) | 0.0253 (6) | 0.0250 (6) | 0.0011 (5) | 0.0084 (5) | −0.0006 (5) |
| N4 | 0.0313 (6) | 0.0278 (6) | 0.0271 (6) | 0.0023 (5) | 0.0095 (5) | −0.0010 (5) |
| N5 | 0.0281 (6) | 0.0298 (6) | 0.0245 (6) | −0.0007 (5) | 0.0092 (5) | −0.0011 (5) |
| N6 | 0.0302 (6) | 0.0329 (7) | 0.0273 (6) | −0.0052 (5) | 0.0101 (5) | −0.0023 (5) |
| C1 | 0.0269 (7) | 0.0274 (7) | 0.0251 (7) | −0.0023 (6) | 0.0062 (6) | −0.0003 (6) |
| C2 | 0.0290 (7) | 0.0303 (7) | 0.0215 (7) | 0.0008 (6) | 0.0057 (6) | −0.0001 (6) |
| C3 | 0.0342 (8) | 0.0295 (8) | 0.0311 (8) | −0.0011 (6) | 0.0089 (6) | −0.0013 (6) |
| C4 | 0.0398 (9) | 0.0309 (8) | 0.0380 (9) | 0.0029 (7) | 0.0110 (7) | −0.0053 (7) |
| C5 | 0.0353 (8) | 0.0371 (8) | 0.0345 (8) | 0.0048 (7) | 0.0137 (7) | −0.0032 (6) |
| C6 | 0.0300 (7) | 0.0337 (8) | 0.0283 (8) | 0.0008 (6) | 0.0100 (6) | −0.0002 (6) |
| C7 | 0.0274 (7) | 0.0289 (7) | 0.0227 (7) | 0.0013 (6) | 0.0052 (6) | 0.0008 (6) |
| C8 | 0.0268 (7) | 0.0279 (7) | 0.0222 (7) | 0.0009 (6) | 0.0078 (6) | 0.0025 (6) |
| C9 | 0.0291 (7) | 0.0254 (7) | 0.0268 (7) | 0.0021 (6) | 0.0104 (6) | 0.0043 (6) |
| C10 | 0.0317 (8) | 0.0223 (7) | 0.0296 (8) | 0.0018 (6) | 0.0076 (6) | 0.0030 (6) |
| C11 | 0.0336 (8) | 0.0270 (7) | 0.0351 (8) | 0.0022 (6) | 0.0106 (7) | 0.0025 (6) |
| C12 | 0.0297 (8) | 0.0284 (8) | 0.0418 (9) | 0.0006 (6) | 0.0047 (7) | 0.0035 (6) |
| C13 | 0.0373 (8) | 0.0247 (7) | 0.0349 (8) | 0.0010 (6) | −0.0011 (7) | 0.0022 (6) |
| C14 | 0.0396 (8) | 0.0245 (7) | 0.0291 (8) | 0.0036 (6) | 0.0054 (6) | 0.0030 (6) |
| C15 | 0.0333 (8) | 0.0230 (7) | 0.0286 (8) | 0.0025 (6) | 0.0065 (6) | 0.0029 (6) |
| C16 | 0.0314 (8) | 0.0253 (7) | 0.0255 (7) | 0.0032 (6) | 0.0076 (6) | −0.0002 (6) |
| C17 | 0.0279 (7) | 0.0311 (8) | 0.0254 (7) | 0.0018 (6) | 0.0098 (6) | −0.0024 (6) |
| C18 | 0.0252 (7) | 0.0344 (8) | 0.0269 (7) | −0.0008 (6) | 0.0101 (6) | −0.0002 (6) |
| C19 | 0.0285 (7) | 0.0403 (9) | 0.0268 (8) | −0.0026 (6) | 0.0082 (6) | −0.0013 (6) |
| C20 | 0.0378 (9) | 0.0502 (10) | 0.0262 (8) | −0.0074 (7) | 0.0099 (7) | 0.0025 (7) |
| C21 | 0.0507 (10) | 0.0447 (9) | 0.0334 (9) | −0.0138 (8) | 0.0134 (8) | 0.0048 (7) |
| C22 | 0.0448 (9) | 0.0382 (9) | 0.0341 (9) | −0.0124 (7) | 0.0130 (7) | −0.0005 (7) |
| C23 | 0.0291 (8) | 0.0371 (8) | 0.0277 (8) | −0.0052 (6) | 0.0113 (6) | −0.0004 (6) |
| C24 | 0.0277 (7) | 0.0312 (8) | 0.0269 (7) | −0.0037 (6) | 0.0089 (6) | −0.0010 (6) |
| C25 | 0.0266 (7) | 0.0333 (8) | 0.0331 (8) | 0.0027 (6) | 0.0089 (6) | 0.0001 (6) |
| C26 | 0.0429 (10) | 0.0640 (12) | 0.0395 (9) | 0.0200 (9) | 0.0086 (8) | 0.0086 (9) |
| C27 | 0.0355 (9) | 0.0340 (8) | 0.0497 (10) | 0.0012 (7) | 0.0096 (7) | −0.0071 (7) |
| C28 | 0.0351 (9) | 0.0407 (9) | 0.0568 (11) | −0.0060 (7) | 0.0160 (8) | −0.0049 (8) |
| B1 | 0.0285 (8) | 0.0287 (8) | 0.0254 (8) | 0.0011 (7) | 0.0096 (7) | −0.0004 (7) |
Geometric parameters (Å, º) top
| O1—B1 | 1.4146 (19) | C11—H11A | 0.9500 |
| O1—C25 | 1.4399 (17) | C12—C13 | 1.398 (2) |
| N1—C8 | 1.3578 (17) | C12—H12A | 0.9500 |
| N1—C1 | 1.3620 (18) | C13—C14 | 1.380 (2) |
| N1—B1 | 1.5040 (19) | C13—H13A | 0.9500 |
| N2—C9 | 1.3432 (18) | C14—C15 | 1.392 (2) |
| N2—C8 | 1.3480 (18) | C14—H14A | 0.9500 |
| N3—C9 | 1.3675 (17) | C15—C16 | 1.456 (2) |
| N3—C16 | 1.3684 (18) | C17—C18 | 1.454 (2) |
| N3—B1 | 1.515 (2) | C18—C19 | 1.393 (2) |
| N4—C16 | 1.3434 (18) | C18—C23 | 1.422 (2) |
| N4—C17 | 1.3461 (19) | C19—C20 | 1.381 (2) |
| N5—C24 | 1.3679 (18) | C19—H19A | 0.9500 |
| N5—C17 | 1.3715 (18) | C20—C21 | 1.400 (2) |
| N5—B1 | 1.5110 (19) | C20—H20A | 0.9500 |
| N6—C1 | 1.3416 (18) | C21—C22 | 1.382 (2) |
| N6—C24 | 1.3450 (18) | C21—H21A | 0.9500 |
| C1—C2 | 1.4554 (19) | C22—C23 | 1.393 (2) |
| C2—C3 | 1.393 (2) | C22—H22A | 0.9500 |
| C2—C7 | 1.4222 (19) | C23—C24 | 1.4581 (19) |
| C3—C4 | 1.383 (2) | C25—C27 | 1.517 (2) |
| C3—H3A | 0.9500 | C25—C28 | 1.519 (2) |
| C4—C5 | 1.398 (2) | C25—C26 | 1.519 (2) |
| C4—H4A | 0.9500 | C26—H26A | 0.9800 |
| C5—C6 | 1.382 (2) | C26—H26B | 0.9800 |
| C5—H5A | 0.9500 | C26—H26C | 0.9800 |
| C6—C7 | 1.389 (2) | C27—H27A | 0.9800 |
| C6—H6A | 0.9500 | C27—H27B | 0.9800 |
| C7—C8 | 1.4568 (19) | C27—H27C | 0.9800 |
| C9—C10 | 1.457 (2) | C28—H28A | 0.9800 |
| C10—C11 | 1.394 (2) | C28—H28B | 0.9800 |
| C10—C15 | 1.418 (2) | C28—H28C | 0.9800 |
| C11—C12 | 1.384 (2) | ||
| B1—O1—C25 | 129.23 (11) | N4—C16—N3 | 122.50 (13) |
| C8—N1—C1 | 113.47 (11) | N4—C16—C15 | 129.27 (13) |
| C8—N1—B1 | 123.58 (12) | N3—C16—C15 | 106.24 (11) |
| C1—N1—B1 | 122.73 (12) | N4—C17—N5 | 123.14 (12) |
| C9—N2—C8 | 116.87 (11) | N4—C17—C18 | 129.16 (13) |
| C9—N3—C16 | 112.29 (12) | N5—C17—C18 | 105.88 (12) |
| C9—N3—B1 | 122.59 (11) | C19—C18—C23 | 120.58 (13) |
| C16—N3—B1 | 123.92 (11) | C19—C18—C17 | 131.82 (13) |
| C16—N4—C17 | 116.60 (12) | C23—C18—C17 | 107.32 (12) |
| C24—N5—C17 | 112.64 (12) | C20—C19—C18 | 118.15 (14) |
| C24—N5—B1 | 122.08 (12) | C20—C19—H19A | 120.9 |
| C17—N5—B1 | 123.57 (12) | C18—C19—H19A | 120.9 |
| C1—N6—C24 | 116.70 (12) | C19—C20—C21 | 121.16 (14) |
| N6—C1—N1 | 122.22 (12) | C19—C20—H20A | 119.4 |
| N6—C1—C2 | 130.26 (13) | C21—C20—H20A | 119.4 |
| N1—C1—C2 | 105.81 (11) | C22—C21—C20 | 121.65 (15) |
| C3—C2—C7 | 120.92 (13) | C22—C21—H21A | 119.2 |
| C3—C2—C1 | 132.32 (13) | C20—C21—H21A | 119.2 |
| C7—C2—C1 | 106.68 (12) | C21—C22—C23 | 117.85 (15) |
| C4—C3—C2 | 117.92 (14) | C21—C22—H22A | 121.1 |
| C4—C3—H3A | 121.0 | C23—C22—H22A | 121.1 |
| C2—C3—H3A | 121.0 | C22—C23—C18 | 120.56 (13) |
| C3—C4—C5 | 121.31 (14) | C22—C23—C24 | 132.13 (14) |
| C3—C4—H4A | 119.3 | C18—C23—C24 | 106.93 (12) |
| C5—C4—H4A | 119.3 | N6—C24—N5 | 123.26 (12) |
| C6—C5—C4 | 121.19 (14) | N6—C24—C23 | 128.78 (13) |
| C6—C5—H5A | 119.4 | N5—C24—C23 | 106.00 (12) |
| C4—C5—H5A | 119.4 | O1—C25—C27 | 111.56 (12) |
| C5—C6—C7 | 118.59 (14) | O1—C25—C28 | 109.25 (12) |
| C5—C6—H6A | 120.7 | C27—C25—C28 | 110.53 (13) |
| C7—C6—H6A | 120.7 | O1—C25—C26 | 103.89 (11) |
| C6—C7—C2 | 119.99 (13) | C27—C25—C26 | 110.78 (14) |
| C6—C7—C8 | 132.61 (13) | C28—C25—C26 | 110.64 (14) |
| C2—C7—C8 | 107.33 (11) | C25—C26—H26A | 109.5 |
| N2—C8—N1 | 121.96 (12) | C25—C26—H26B | 109.5 |
| N2—C8—C7 | 131.15 (12) | H26A—C26—H26B | 109.5 |
| N1—C8—C7 | 105.54 (11) | C25—C26—H26C | 109.5 |
| N2—C9—N3 | 122.85 (13) | H26A—C26—H26C | 109.5 |
| N2—C9—C10 | 129.72 (12) | H26B—C26—H26C | 109.5 |
| N3—C9—C10 | 105.95 (12) | C25—C27—H27A | 109.5 |
| C11—C10—C15 | 120.32 (13) | C25—C27—H27B | 109.5 |
| C11—C10—C9 | 132.12 (13) | H27A—C27—H27B | 109.5 |
| C15—C10—C9 | 107.31 (12) | C25—C27—H27C | 109.5 |
| C12—C11—C10 | 118.16 (14) | H27A—C27—H27C | 109.5 |
| C12—C11—H11A | 120.9 | H27B—C27—H27C | 109.5 |
| C10—C11—H11A | 120.9 | C25—C28—H28A | 109.5 |
| C11—C12—C13 | 121.32 (14) | C25—C28—H28B | 109.5 |
| C11—C12—H12A | 119.3 | H28A—C28—H28B | 109.5 |
| C13—C12—H12A | 119.3 | C25—C28—H28C | 109.5 |
| C14—C13—C12 | 121.18 (14) | H28A—C28—H28C | 109.5 |
| C14—C13—H13A | 119.4 | H28B—C28—H28C | 109.5 |
| C12—C13—H13A | 119.4 | O1—B1—N1 | 108.82 (12) |
| C13—C14—C15 | 118.26 (14) | O1—B1—N5 | 120.99 (12) |
| C13—C14—H14A | 120.9 | N1—B1—N5 | 102.59 (11) |
| C15—C14—H14A | 120.9 | O1—B1—N3 | 117.50 (12) |
| C14—C15—C10 | 120.70 (13) | N1—B1—N3 | 102.13 (11) |
| C14—C15—C16 | 132.32 (13) | N5—B1—N3 | 102.33 (11) |
| C10—C15—C16 | 106.79 (12) | ||
| C24—N6—C1—N1 | −6.2 (2) | C10—C15—C16—N4 | 156.41 (14) |
| C24—N6—C1—C2 | 156.75 (14) | C14—C15—C16—N3 | 177.62 (14) |
| C8—N1—C1—N6 | 155.21 (13) | C10—C15—C16—N3 | −7.51 (15) |
| B1—N1—C1—N6 | −19.7 (2) | C16—N4—C17—N5 | −10.1 (2) |
| C8—N1—C1—C2 | −11.33 (16) | C16—N4—C17—C18 | 152.35 (14) |
| B1—N1—C1—C2 | 173.79 (12) | C24—N5—C17—N4 | 154.67 (13) |
| N6—C1—C2—C3 | 18.9 (3) | B1—N5—C17—N4 | −10.7 (2) |
| N1—C1—C2—C3 | −176.02 (15) | C24—N5—C17—C18 | −11.22 (15) |
| N6—C1—C2—C7 | −157.83 (14) | B1—N5—C17—C18 | −176.55 (12) |
| N1—C1—C2—C7 | 7.22 (15) | N4—C17—C18—C19 | 15.4 (3) |
| C7—C2—C3—C4 | −1.2 (2) | N5—C17—C18—C19 | −179.91 (15) |
| C1—C2—C3—C4 | −177.55 (14) | N4—C17—C18—C23 | −158.39 (14) |
| C2—C3—C4—C5 | 1.9 (2) | N5—C17—C18—C23 | 6.35 (15) |
| C3—C4—C5—C6 | −0.3 (2) | C23—C18—C19—C20 | −1.5 (2) |
| C4—C5—C6—C7 | −2.1 (2) | C17—C18—C19—C20 | −174.57 (15) |
| C5—C6—C7—C2 | 2.7 (2) | C18—C19—C20—C21 | 2.3 (2) |
| C5—C6—C7—C8 | 179.19 (15) | C19—C20—C21—C22 | −0.8 (3) |
| C3—C2—C7—C6 | −1.1 (2) | C20—C21—C22—C23 | −1.4 (3) |
| C1—C2—C7—C6 | 176.06 (13) | C21—C22—C23—C18 | 2.1 (2) |
| C3—C2—C7—C8 | −178.40 (13) | C21—C22—C23—C24 | 173.96 (16) |
| C1—C2—C7—C8 | −1.19 (15) | C19—C18—C23—C22 | −0.7 (2) |
| C9—N2—C8—N1 | 7.97 (19) | C17—C18—C23—C22 | 173.92 (14) |
| C9—N2—C8—C7 | −156.70 (14) | C19—C18—C23—C24 | −174.38 (13) |
| C1—N1—C8—N2 | −157.53 (13) | C17—C18—C23—C24 | 0.21 (16) |
| B1—N1—C8—N2 | 17.3 (2) | C1—N6—C24—N5 | 10.0 (2) |
| C1—N1—C8—C7 | 10.55 (15) | C1—N6—C24—C23 | −151.74 (14) |
| B1—N1—C8—C7 | −174.62 (12) | C17—N5—C24—N6 | −153.95 (13) |
| C6—C7—C8—N2 | −15.5 (3) | B1—N5—C24—N6 | 11.6 (2) |
| C2—C7—C8—N2 | 161.26 (14) | C17—N5—C24—C23 | 11.36 (16) |
| C6—C7—C8—N1 | 177.95 (15) | B1—N5—C24—C23 | 176.94 (12) |
| C2—C7—C8—N1 | −5.28 (15) | C22—C23—C24—N6 | −15.2 (3) |
| C8—N2—C9—N3 | −10.19 (19) | C18—C23—C24—N6 | 157.52 (14) |
| C8—N2—C9—C10 | 153.89 (14) | C22—C23—C24—N5 | −179.40 (16) |
| C16—N3—C9—N2 | 155.48 (13) | C18—C23—C24—N5 | −6.70 (16) |
| B1—N3—C9—N2 | −12.4 (2) | B1—O1—C25—C27 | 49.70 (19) |
| C16—N3—C9—C10 | −11.85 (15) | B1—O1—C25—C28 | −72.81 (18) |
| B1—N3—C9—C10 | −179.74 (12) | B1—O1—C25—C26 | 169.09 (15) |
| N2—C9—C10—C11 | 14.4 (3) | C25—O1—B1—N1 | 154.31 (12) |
| N3—C9—C10—C11 | −179.50 (14) | C25—O1—B1—N5 | 36.1 (2) |
| N2—C9—C10—C15 | −159.66 (14) | C25—O1—B1—N3 | −90.36 (17) |
| N3—C9—C10—C15 | 6.47 (15) | C8—N1—B1—O1 | 91.35 (16) |
| C15—C10—C11—C12 | −2.5 (2) | C1—N1—B1—O1 | −94.29 (15) |
| C9—C10—C11—C12 | −175.92 (14) | C8—N1—B1—N5 | −139.34 (13) |
| C10—C11—C12—C13 | 1.5 (2) | C1—N1—B1—N5 | 35.02 (17) |
| C11—C12—C13—C14 | 0.8 (2) | C8—N1—B1—N3 | −33.56 (17) |
| C12—C13—C14—C15 | −2.0 (2) | C1—N1—B1—N3 | 140.79 (12) |
| C13—C14—C15—C10 | 0.9 (2) | C24—N5—B1—O1 | 90.43 (17) |
| C13—C14—C15—C16 | 175.22 (14) | C17—N5—B1—O1 | −105.58 (16) |
| C11—C10—C15—C14 | 1.4 (2) | C24—N5—B1—N1 | −30.88 (17) |
| C9—C10—C15—C14 | 176.22 (12) | C17—N5—B1—N1 | 133.10 (13) |
| C11—C10—C15—C16 | −174.24 (12) | C24—N5—B1—N3 | −136.51 (13) |
| C9—C10—C15—C16 | 0.63 (15) | C17—N5—B1—N3 | 27.48 (17) |
| C17—N4—C16—N3 | 8.1 (2) | C9—N3—B1—O1 | −88.02 (16) |
| C17—N4—C16—C15 | −153.56 (14) | C16—N3—B1—O1 | 105.50 (15) |
| C9—N3—C16—N4 | −153.00 (13) | C9—N3—B1—N1 | 30.93 (16) |
| B1—N3—C16—N4 | 14.7 (2) | C16—N3—B1—N1 | −135.55 (13) |
| C9—N3—C16—C15 | 12.28 (15) | C9—N3—B1—N5 | 136.90 (12) |
| B1—N3—C16—C15 | 179.99 (12) | C16—N3—B1—N5 | −29.58 (17) |
| C14—C15—C16—N4 | −18.5 (3) |
(Octanolato)(subphthalocyaninato)boron (d23123_a) top
Crystal data top
| 6C32H29BN6O·2H2O0.50 | Z = 1 |
| Mr = 3166.55 | F(000) = 1668 |
| Triclinic, P1 | Dx = 1.314 Mg m−3 |
| a = 15.3028 (7) Å | Cu Kα radiation, λ = 1.54178 Å |
| b = 16.2278 (7) Å | Cell parameters from 6400 reflections |
| c = 17.3604 (7) Å | θ = 2.7–63.9° |
| α = 103.045 (3)° | µ = 0.65 mm−1 |
| β = 105.716 (3)° | T = 150 K |
| γ = 94.022 (3)° | Shard, pink |
| V = 4003.0 (3) Å3 | 0.24 × 0.16 × 0.06 mm |
Data collection top
| Bruker Kappa APEX-DUO CMOS PHOTON II diffractometer | 10618 reflections with I > 2σ(I) |
| Radiation source: Incoatec ImuS with multi-layer optics | Rint = 0.070 |
| φ and ω scans | θmax = 66.4°, θmin = 2.7° |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −17→18 |
| Tmin = 0.622, Tmax = 0.753 | k = −19→19 |
| 110436 measured reflections | l = −20→20 |
| 13816 independent reflections |
Refinement top
| Refinement on F2 | Hydrogen site location: mixed |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.054 | w = 1/[σ2(Fo2) + (0.0697P)2 + 2.1766P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.149 | (Δ/σ)max < 0.001 |
| S = 1.05 | Δρmax = 0.61 e Å−3 |
| 13816 reflections | Δρmin = −0.38 e Å−3 |
| 1201 parameters | Extinction correction: SHELXL2019 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| 499 restraints | Extinction coefficient: 0.00223 (15) |
| Primary atom site location: structure-invariant direct methods |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | Occ. (<1) | |
| O1A | 0.77624 (11) | 0.36183 (10) | 0.70390 (9) | 0.0390 (4) | |
| N1A | 0.65242 (12) | 0.26603 (12) | 0.59626 (10) | 0.0316 (4) | |
| N2A | 0.71668 (12) | 0.13671 (12) | 0.57327 (10) | 0.0326 (4) | |
| N3A | 0.72729 (12) | 0.21399 (12) | 0.71030 (10) | 0.0303 (4) | |
| N4A | 0.67121 (12) | 0.23869 (12) | 0.82811 (10) | 0.0332 (4) | |
| N5A | 0.62832 (12) | 0.31692 (12) | 0.72638 (11) | 0.0332 (4) | |
| N6A | 0.52633 (13) | 0.34070 (12) | 0.60570 (11) | 0.0380 (5) | |
| C1A | 0.57428 (15) | 0.29578 (14) | 0.56100 (13) | 0.0337 (5) | |
| C2A | 0.54488 (15) | 0.24989 (15) | 0.47383 (13) | 0.0345 (5) | |
| C3A | 0.46960 (17) | 0.25264 (16) | 0.40831 (14) | 0.0395 (6) | |
| H3AA | 0.430692 | 0.295265 | 0.414304 | 0.047* | |
| C4A | 0.45320 (17) | 0.19143 (17) | 0.33424 (14) | 0.0426 (6) | |
| H4AA | 0.402382 | 0.192387 | 0.288788 | 0.051* | |
| C5A | 0.50962 (17) | 0.12849 (17) | 0.32495 (14) | 0.0406 (6) | |
| H5AA | 0.496195 | 0.087195 | 0.273400 | 0.049* | |
| C6A | 0.58470 (16) | 0.12477 (16) | 0.38906 (13) | 0.0370 (5) | |
| H6AA | 0.622853 | 0.081622 | 0.382273 | 0.044* | |
| C7A | 0.60278 (15) | 0.18617 (15) | 0.46395 (13) | 0.0328 (5) | |
| C8A | 0.66774 (14) | 0.19482 (14) | 0.54496 (13) | 0.0313 (5) | |
| C9A | 0.74113 (14) | 0.14480 (14) | 0.65553 (13) | 0.0309 (5) | |
| C10A | 0.75977 (14) | 0.07926 (15) | 0.70003 (13) | 0.0321 (5) | |
| C11A | 0.77972 (15) | −0.00374 (16) | 0.67651 (14) | 0.0376 (5) | |
| H11A | 0.789968 | −0.024741 | 0.624462 | 0.045* | |
| C12A | 0.78409 (17) | −0.05425 (17) | 0.73115 (15) | 0.0442 (6) | |
| H12A | 0.798119 | −0.110721 | 0.716502 | 0.053* | |
| C13A | 0.76830 (18) | −0.02420 (17) | 0.80787 (16) | 0.0458 (6) | |
| H13A | 0.771315 | −0.060867 | 0.843862 | 0.055* | |
| C14A | 0.74848 (16) | 0.05751 (16) | 0.83205 (14) | 0.0390 (5) | |
| H14A | 0.737483 | 0.077359 | 0.883948 | 0.047* | |
| C15A | 0.74499 (14) | 0.11037 (15) | 0.77825 (13) | 0.0319 (5) | |
| C16A | 0.71809 (14) | 0.19458 (15) | 0.78081 (12) | 0.0321 (5) | |
| C17A | 0.62236 (15) | 0.29559 (14) | 0.79709 (13) | 0.0333 (5) | |
| C18A | 0.54126 (15) | 0.32801 (14) | 0.81356 (13) | 0.0347 (5) | |
| C19A | 0.50171 (16) | 0.32619 (15) | 0.87688 (14) | 0.0375 (5) | |
| H19A | 0.531442 | 0.305859 | 0.923105 | 0.045* | |
| C20A | 0.41774 (16) | 0.35503 (15) | 0.86993 (15) | 0.0414 (6) | |
| H20A | 0.389700 | 0.354774 | 0.912483 | 0.050* | |
| C21A | 0.37301 (17) | 0.38452 (15) | 0.80207 (16) | 0.0439 (6) | |
| H21A | 0.315361 | 0.403837 | 0.799509 | 0.053* | |
| C22A | 0.41091 (17) | 0.38620 (15) | 0.73843 (15) | 0.0425 (6) | |
| H22A | 0.379886 | 0.405570 | 0.691973 | 0.051* | |
| C23A | 0.49608 (16) | 0.35851 (15) | 0.74487 (14) | 0.0366 (5) | |
| C24A | 0.55087 (16) | 0.34516 (14) | 0.68727 (14) | 0.0357 (5) | |
| C25A | 0.83225 (17) | 0.39292 (17) | 0.78780 (15) | 0.0457 (6) | |
| H25A | 0.802926 | 0.369796 | 0.824250 | 0.055* | |
| H25B | 0.837113 | 0.455978 | 0.804270 | 0.055* | |
| C26A | 0.92488 (19) | 0.3681 (2) | 0.79900 (18) | 0.0624 (8) | |
| H26A | 0.951904 | 0.386498 | 0.758791 | 0.075* | |
| H26B | 0.920434 | 0.305150 | 0.787606 | 0.075* | |
| C27A | 0.98796 (19) | 0.4084 (2) | 0.88718 (18) | 0.0583 (7) | |
| H27A | 0.988059 | 0.471077 | 0.899872 | 0.070* | |
| H27B | 0.962854 | 0.386659 | 0.926818 | 0.070* | |
| C28A | 1.0846 (2) | 0.3902 (2) | 0.8993 (2) | 0.0710 (9) | |
| H28A | 1.108246 | 0.408854 | 0.857407 | 0.085* | |
| H28B | 1.084609 | 0.327667 | 0.889598 | 0.085* | |
| C29A | 1.1493 (2) | 0.4336 (2) | 0.98479 (18) | 0.0581 (7) | |
| H29A | 1.145916 | 0.495693 | 0.996609 | 0.070* | |
| H29B | 1.128971 | 0.411305 | 1.026644 | 0.070* | |
| C30A | 1.24692 (19) | 0.41957 (19) | 0.99252 (17) | 0.0532 (7) | |
| H30A | 1.264479 | 0.435496 | 0.946411 | 0.064* | |
| H30B | 1.251065 | 0.357980 | 0.986755 | 0.064* | |
| C31A | 1.31477 (19) | 0.46988 (17) | 1.07356 (15) | 0.0486 (6) | |
| H31A | 1.310528 | 0.531503 | 1.079745 | 0.058* | |
| H31B | 1.297984 | 0.453492 | 1.119810 | 0.058* | |
| C32A | 1.41249 (18) | 0.45535 (17) | 1.07933 (16) | 0.0484 (6) | |
| H32A | 1.453270 | 0.489286 | 1.132747 | 0.073* | |
| H32B | 1.417524 | 0.394647 | 1.074539 | 0.073* | |
| H32C | 1.430073 | 0.472690 | 1.034459 | 0.073* | |
| B1A | 0.70321 (18) | 0.29553 (17) | 0.68701 (15) | 0.0340 (6) | |
| N1B | 0.54418 (12) | 0.17729 (11) | 0.14279 (10) | 0.0290 (4) | |
| N2B | 0.68560 (12) | 0.15591 (11) | 0.22919 (11) | 0.0318 (4) | |
| N3B | 0.63544 (12) | 0.29256 (11) | 0.25022 (11) | 0.0304 (4) | |
| N4B | 0.55947 (13) | 0.39765 (12) | 0.31570 (11) | 0.0339 (4) | |
| N5B | 0.48129 (12) | 0.30104 (11) | 0.18579 (10) | 0.0309 (4) | |
| N6B | 0.38246 (12) | 0.17359 (11) | 0.10262 (10) | 0.0318 (4) | |
| C1B | 0.45758 (15) | 0.13443 (14) | 0.10575 (12) | 0.0292 (5) | |
| C2B | 0.46782 (15) | 0.04419 (14) | 0.09085 (12) | 0.0297 (5) | |
| C3B | 0.40548 (16) | −0.03011 (14) | 0.05101 (13) | 0.0330 (5) | |
| H3BA | 0.342689 | −0.027384 | 0.025991 | 0.040* | |
| C4B | 0.43778 (17) | −0.10798 (15) | 0.04899 (13) | 0.0372 (5) | |
| H4BA | 0.396667 | −0.159300 | 0.021258 | 0.045* | |
| C5B | 0.52956 (17) | −0.11243 (15) | 0.08691 (14) | 0.0375 (5) | |
| H5BA | 0.549824 | −0.166753 | 0.083954 | 0.045* | |
| C6B | 0.59174 (16) | −0.03945 (14) | 0.12875 (13) | 0.0341 (5) | |
| H6BA | 0.653637 | −0.042992 | 0.156134 | 0.041* | |
| C7B | 0.56093 (15) | 0.03915 (14) | 0.12949 (12) | 0.0300 (5) | |
| C8B | 0.60736 (15) | 0.12615 (14) | 0.16756 (13) | 0.0297 (5) | |
| C9B | 0.69478 (14) | 0.23733 (14) | 0.27341 (13) | 0.0311 (5) | |
| C10B | 0.74647 (15) | 0.27666 (14) | 0.35949 (13) | 0.0322 (5) | |
| C11B | 0.81553 (15) | 0.24968 (15) | 0.41503 (14) | 0.0362 (5) | |
| H11C | 0.842541 | 0.200634 | 0.397411 | 0.043* | |
| C12B | 0.84344 (17) | 0.29682 (16) | 0.49675 (14) | 0.0408 (6) | |
| H12C | 0.890512 | 0.279686 | 0.535696 | 0.049* | |
| C13B | 0.80404 (17) | 0.36904 (16) | 0.52340 (14) | 0.0407 (6) | |
| H13C | 0.824908 | 0.399989 | 0.579932 | 0.049* | |
| C14B | 0.73544 (16) | 0.39605 (15) | 0.46901 (14) | 0.0371 (5) | |
| H14C | 0.708348 | 0.444746 | 0.487447 | 0.045* | |
| C15B | 0.70689 (15) | 0.35006 (14) | 0.38632 (13) | 0.0322 (5) | |
| C16B | 0.63209 (15) | 0.35593 (14) | 0.31657 (13) | 0.0322 (5) | |
| C17B | 0.48290 (15) | 0.36609 (14) | 0.25208 (13) | 0.0321 (5) | |
| C18B | 0.38776 (15) | 0.37471 (15) | 0.24656 (13) | 0.0346 (5) | |
| C19B | 0.34798 (17) | 0.43257 (16) | 0.29397 (15) | 0.0415 (6) | |
| H19C | 0.384550 | 0.477172 | 0.339221 | 0.050* | |
| C20B | 0.25313 (18) | 0.42293 (17) | 0.27291 (16) | 0.0471 (6) | |
| H20C | 0.224098 | 0.462690 | 0.303123 | 0.057* | |
| C21B | 0.19961 (18) | 0.35591 (18) | 0.20819 (16) | 0.0474 (6) | |
| H21C | 0.134749 | 0.351248 | 0.195306 | 0.057* | |
| C22B | 0.23781 (16) | 0.29607 (16) | 0.16222 (15) | 0.0411 (6) | |
| H22C | 0.200487 | 0.249811 | 0.119247 | 0.049* | |
| C23B | 0.33295 (16) | 0.30587 (15) | 0.18100 (13) | 0.0353 (5) | |
| C24B | 0.39575 (15) | 0.25567 (14) | 0.14705 (13) | 0.0317 (5) | |
| O1B | 0.59133 (11) | 0.30152 (9) | 0.10243 (9) | 0.0359 (4) | |
| C25B | 0.63545 (18) | 0.38710 (15) | 0.12029 (16) | 0.0435 (6) | 0.735 (5) |
| H25C | 0.627306 | 0.421193 | 0.172233 | 0.052* | 0.735 (5) |
| H25D | 0.606933 | 0.413429 | 0.075114 | 0.052* | 0.735 (5) |
| C26B | 0.7365 (2) | 0.3880 (2) | 0.1291 (2) | 0.0626 (7) | 0.735 (5) |
| H26C | 0.767364 | 0.447762 | 0.148176 | 0.075* | 0.735 (5) |
| H26D | 0.763897 | 0.357832 | 0.171537 | 0.075* | 0.735 (5) |
| C27B | 0.7525 (3) | 0.3457 (3) | 0.0487 (3) | 0.0637 (12) | 0.735 (5) |
| H27C | 0.732392 | 0.381163 | 0.009393 | 0.076* | 0.735 (5) |
| H27D | 0.712649 | 0.289832 | 0.025785 | 0.076* | 0.735 (5) |
| C28B | 0.8512 (3) | 0.3304 (4) | 0.0517 (4) | 0.0877 (16) | 0.735 (5) |
| H28C | 0.851797 | 0.303487 | −0.005252 | 0.105* | 0.735 (5) |
| H28D | 0.889985 | 0.386726 | 0.069637 | 0.105* | 0.735 (5) |
| C29B | 0.8957 (4) | 0.2757 (4) | 0.1074 (4) | 0.1024 (17) | 0.735 (5) |
| H29C | 0.888217 | 0.297551 | 0.162934 | 0.123* | 0.735 (5) |
| H29D | 0.962232 | 0.281643 | 0.113476 | 0.123* | 0.735 (5) |
| C30B | 0.8554 (4) | 0.1785 (3) | 0.0748 (3) | 0.1314 (16) | 0.735 (5) |
| H30C | 0.787696 | 0.171374 | 0.060540 | 0.158* | 0.735 (5) |
| H30D | 0.872783 | 0.152406 | 0.024752 | 0.158* | 0.735 (5) |
| C31B | 0.8961 (3) | 0.1354 (4) | 0.1454 (3) | 0.0941 (17) | 0.735 (5) |
| H31C | 0.886617 | 0.167521 | 0.197569 | 0.113* | 0.735 (5) |
| H31D | 0.864446 | 0.076314 | 0.131499 | 0.113* | 0.735 (5) |
| C32B | 0.9955 (4) | 0.1343 (4) | 0.1564 (4) | 0.144 (2) | 0.735 (5) |
| H32D | 1.021209 | 0.107092 | 0.200944 | 0.217* | 0.735 (5) |
| H32E | 1.004480 | 0.101969 | 0.104803 | 0.217* | 0.735 (5) |
| H32F | 1.026597 | 0.192952 | 0.170710 | 0.217* | 0.735 (5) |
| C25D | 0.63545 (18) | 0.38710 (15) | 0.12029 (16) | 0.0435 (6) | 0.265 (5) |
| H25E | 0.627306 | 0.421193 | 0.172233 | 0.052* | 0.265 (5) |
| H25F | 0.606933 | 0.413429 | 0.075114 | 0.052* | 0.265 (5) |
| C26D | 0.7365 (2) | 0.3880 (2) | 0.1291 (2) | 0.0626 (7) | 0.265 (5) |
| H26E | 0.759478 | 0.443635 | 0.122305 | 0.075* | 0.265 (5) |
| H26F | 0.767371 | 0.386839 | 0.186856 | 0.075* | 0.265 (5) |
| C27D | 0.7678 (8) | 0.3223 (8) | 0.0756 (9) | 0.075 (3) | 0.265 (5) |
| H27E | 0.738522 | 0.322925 | 0.017478 | 0.090* | 0.265 (5) |
| H27F | 0.746795 | 0.266020 | 0.082469 | 0.090* | 0.265 (5) |
| C28D | 0.8736 (8) | 0.3314 (8) | 0.0916 (10) | 0.084 (3) | 0.265 (5) |
| H28E | 0.905607 | 0.337598 | 0.150758 | 0.100* | 0.265 (5) |
| H28F | 0.895531 | 0.381663 | 0.075013 | 0.100* | 0.265 (5) |
| C29D | 0.8904 (10) | 0.2463 (7) | 0.0364 (9) | 0.098 (3) | 0.265 (5) |
| H29E | 0.854867 | 0.237375 | −0.022358 | 0.118* | 0.265 (5) |
| H29F | 0.956241 | 0.246088 | 0.040819 | 0.118* | 0.265 (5) |
| C30D | 0.8554 (4) | 0.1785 (3) | 0.0748 (3) | 0.1314 (16) | 0.265 (5) |
| H30E | 0.852391 | 0.206273 | 0.130823 | 0.158* | 0.265 (5) |
| H30F | 0.792896 | 0.151282 | 0.040352 | 0.158* | 0.265 (5) |
| C31D | 0.9189 (10) | 0.1114 (9) | 0.0803 (9) | 0.124 (3) | 0.265 (5) |
| H31E | 0.883335 | 0.056693 | 0.077173 | 0.149* | 0.265 (5) |
| H31F | 0.943316 | 0.102492 | 0.032204 | 0.149* | 0.265 (5) |
| C32D | 0.9955 (4) | 0.1343 (4) | 0.1564 (4) | 0.144 (2) | 0.265 (5) |
| H32M | 1.034230 | 0.088641 | 0.156635 | 0.217* | 0.265 (5) |
| H32N | 1.031882 | 0.187663 | 0.159298 | 0.217* | 0.265 (5) |
| H32O | 0.971874 | 0.141843 | 0.204287 | 0.217* | 0.265 (5) |
| B1B | 0.56605 (17) | 0.27289 (16) | 0.16599 (15) | 0.0312 (5) | |
| N1C | 0.13334 (12) | 0.19929 (11) | 0.72603 (10) | 0.0318 (4) | |
| N2C | −0.02401 (12) | 0.14414 (12) | 0.65772 (10) | 0.0339 (4) | |
| N3C | 0.07636 (12) | 0.17606 (11) | 0.58153 (10) | 0.0306 (4) | |
| N4C | 0.17635 (12) | 0.14168 (12) | 0.49917 (11) | 0.0344 (4) | |
| N5C | 0.23513 (12) | 0.19534 (12) | 0.64534 (11) | 0.0325 (4) | |
| N6C | 0.28824 (12) | 0.17955 (11) | 0.78215 (11) | 0.0324 (4) | |
| C1C | 0.20267 (15) | 0.18497 (14) | 0.78823 (13) | 0.0316 (5) | |
| C2C | 0.15901 (15) | 0.15785 (14) | 0.84433 (13) | 0.0337 (5) | |
| C3C | 0.19425 (17) | 0.13847 (16) | 0.92022 (13) | 0.0397 (6) | |
| H3CA | 0.258476 | 0.144692 | 0.945766 | 0.048* | |
| C4C | 0.13259 (18) | 0.10997 (19) | 0.95682 (15) | 0.0497 (7) | |
| H4CA | 0.155069 | 0.097960 | 1.009178 | 0.060* | |
| C5C | 0.03801 (19) | 0.0983 (2) | 0.91901 (15) | 0.0540 (7) | |
| H5CA | −0.002178 | 0.078135 | 0.946022 | 0.065* | |
| C6C | 0.00154 (17) | 0.11549 (18) | 0.84299 (14) | 0.0464 (6) | |
| H6CA | −0.062778 | 0.106536 | 0.817119 | 0.056* | |
| C7C | 0.06235 (15) | 0.14635 (15) | 0.80580 (13) | 0.0359 (5) | |
| C8C | 0.04847 (15) | 0.16719 (14) | 0.72637 (13) | 0.0336 (5) | |
| C9C | −0.00699 (15) | 0.14378 (14) | 0.58546 (13) | 0.0308 (5) | |
| C10C | −0.05796 (14) | 0.09803 (13) | 0.50040 (12) | 0.0293 (5) | |
| C11C | −0.14766 (15) | 0.05620 (14) | 0.46462 (13) | 0.0316 (5) | |
| H11B | −0.187949 | 0.052352 | 0.497165 | 0.038* | |
| C12C | −0.17588 (15) | 0.02045 (14) | 0.37984 (13) | 0.0336 (5) | |
| H12B | −0.237360 | −0.006420 | 0.353825 | 0.040* | |
| C13C | −0.11654 (15) | 0.02286 (14) | 0.33174 (13) | 0.0346 (5) | |
| H13B | −0.138655 | −0.001474 | 0.273703 | 0.042* | |
| C14C | −0.02592 (16) | 0.06010 (14) | 0.36707 (13) | 0.0344 (5) | |
| H14B | 0.015165 | 0.059095 | 0.334596 | 0.041* | |
| C15C | 0.00316 (15) | 0.09905 (14) | 0.45160 (13) | 0.0302 (5) | |
| C16C | 0.09146 (15) | 0.14334 (14) | 0.50739 (13) | 0.0315 (5) | |
| C17C | 0.24669 (15) | 0.16291 (14) | 0.56954 (13) | 0.0344 (5) | |
| C18C | 0.33898 (15) | 0.13995 (15) | 0.58579 (14) | 0.0359 (5) | |
| C19C | 0.39147 (16) | 0.11047 (17) | 0.53419 (15) | 0.0416 (6) | |
| H19B | 0.369209 | 0.104444 | 0.476250 | 0.050* | |
| C20C | 0.47704 (16) | 0.09008 (17) | 0.56928 (15) | 0.0441 (6) | |
| H20B | 0.514745 | 0.071477 | 0.535220 | 0.053* | |
| C21C | 0.50874 (16) | 0.09647 (16) | 0.65411 (15) | 0.0407 (6) | |
| H21B | 0.566956 | 0.080349 | 0.676264 | 0.049* | |
| C22C | 0.45746 (15) | 0.12573 (15) | 0.70684 (14) | 0.0364 (5) | |
| H22B | 0.479547 | 0.129540 | 0.764395 | 0.044* | |
| C23C | 0.37277 (15) | 0.14928 (14) | 0.67285 (13) | 0.0335 (5) | |
| C24C | 0.30167 (15) | 0.18014 (14) | 0.70868 (13) | 0.0325 (5) | |
| O1C | 0.15664 (14) | 0.31964 (11) | 0.66693 (12) | 0.0652 (6) | 0.513 (4) |
| C25C | 0.1609 (4) | 0.3589 (3) | 0.6120 (3) | 0.0466 (12) | 0.513 (4) |
| H25G | 0.109155 | 0.332983 | 0.561700 | 0.056* | 0.513 (4) |
| H25H | 0.218272 | 0.349317 | 0.597403 | 0.056* | 0.513 (4) |
| C26C | 0.1585 (4) | 0.4530 (3) | 0.6350 (4) | 0.0455 (13) | 0.513 (4) |
| H26G | 0.179991 | 0.478739 | 0.595716 | 0.055* | 0.513 (4) |
| H26H | 0.201974 | 0.477728 | 0.690846 | 0.055* | 0.513 (4) |
| C27C | 0.0651 (4) | 0.4774 (4) | 0.6353 (5) | 0.0505 (14) | 0.513 (4) |
| H27G | 0.051034 | 0.466293 | 0.684721 | 0.061* | 0.513 (4) |
| H27H | 0.018538 | 0.440629 | 0.585768 | 0.061* | 0.513 (4) |
| C28C | 0.0579 (5) | 0.5704 (5) | 0.6357 (9) | 0.0539 (19) | 0.513 (4) |
| H28G | 0.105235 | 0.606437 | 0.685079 | 0.065* | 0.513 (4) |
| H28H | 0.072989 | 0.580869 | 0.586412 | 0.065* | 0.513 (4) |
| C29C | −0.0339 (4) | 0.6006 (4) | 0.6358 (4) | 0.0590 (14) | 0.513 (4) |
| H29G | −0.046559 | 0.596393 | 0.687862 | 0.071* | 0.513 (4) |
| H29H | −0.082615 | 0.561947 | 0.589354 | 0.071* | 0.513 (4) |
| C30C | −0.0384 (4) | 0.6921 (4) | 0.6279 (5) | 0.0636 (14) | 0.513 (4) |
| H30G | 0.017105 | 0.728830 | 0.667853 | 0.076* | 0.513 (4) |
| H30H | −0.036516 | 0.693653 | 0.571705 | 0.076* | 0.513 (4) |
| C31C | −0.1219 (5) | 0.7304 (5) | 0.6426 (6) | 0.0804 (19) | 0.513 (4) |
| H31G | −0.115212 | 0.791062 | 0.640814 | 0.096* | 0.513 (4) |
| H31H | −0.124484 | 0.728956 | 0.698623 | 0.096* | 0.513 (4) |
| C32C | −0.2115 (8) | 0.6844 (8) | 0.5797 (9) | 0.123 (4) | 0.513 (4) |
| H32G | −0.262620 | 0.712114 | 0.592532 | 0.185* | 0.513 (4) |
| H32H | −0.210267 | 0.686825 | 0.524148 | 0.185* | 0.513 (4) |
| H32I | −0.219547 | 0.624666 | 0.582006 | 0.185* | 0.513 (4) |
| O1E | 0.15664 (14) | 0.31964 (11) | 0.66693 (12) | 0.0652 (6) | 0.487 (4) |
| C25E | 0.0916 (3) | 0.3650 (3) | 0.6582 (3) | 0.0408 (11) | 0.487 (4) |
| H25J | 0.064748 | 0.366466 | 0.704246 | 0.049* | 0.487 (4) |
| H25K | 0.043259 | 0.336133 | 0.606179 | 0.049* | 0.487 (4) |
| C26E | 0.1162 (5) | 0.4543 (3) | 0.6559 (4) | 0.0387 (12) | 0.487 (4) |
| H26J | 0.133138 | 0.453758 | 0.604625 | 0.046* | 0.487 (4) |
| H26K | 0.170502 | 0.481387 | 0.703488 | 0.046* | 0.487 (4) |
| C27E | 0.0390 (4) | 0.5076 (4) | 0.6587 (4) | 0.0457 (14) | 0.487 (4) |
| H27J | 0.027900 | 0.515021 | 0.713227 | 0.055* | 0.487 (4) |
| H27K | −0.017703 | 0.476710 | 0.615781 | 0.055* | 0.487 (4) |
| C28E | 0.0598 (6) | 0.5949 (5) | 0.6446 (8) | 0.0510 (18) | 0.487 (4) |
| H28J | 0.063627 | 0.586915 | 0.587408 | 0.061* | 0.487 (4) |
| H28K | 0.120840 | 0.622048 | 0.682711 | 0.061* | 0.487 (4) |
| C29E | −0.0093 (4) | 0.6559 (5) | 0.6569 (4) | 0.0615 (15) | 0.487 (4) |
| H29J | −0.016984 | 0.660866 | 0.712551 | 0.074* | 0.487 (4) |
| H29K | 0.015268 | 0.713194 | 0.654933 | 0.074* | 0.487 (4) |
| C30E | −0.1017 (4) | 0.6279 (4) | 0.5931 (5) | 0.0760 (17) | 0.487 (4) |
| H30J | −0.130677 | 0.574861 | 0.600377 | 0.091* | 0.487 (4) |
| H30K | −0.093551 | 0.615192 | 0.537181 | 0.091* | 0.487 (4) |
| C31E | −0.1651 (7) | 0.6971 (6) | 0.6003 (7) | 0.075 (2) | 0.487 (4) |
| H31J | −0.135608 | 0.751899 | 0.596813 | 0.090* | 0.487 (4) |
| H31K | −0.179780 | 0.706188 | 0.653416 | 0.090* | 0.487 (4) |
| C32E | −0.2526 (8) | 0.6626 (8) | 0.5266 (8) | 0.120 (4) | 0.487 (4) |
| H32J | −0.296217 | 0.704047 | 0.527533 | 0.180* | 0.487 (4) |
| H32K | −0.236666 | 0.653725 | 0.474601 | 0.180* | 0.487 (4) |
| H32L | −0.280579 | 0.608281 | 0.530872 | 0.180* | 0.487 (4) |
| B1C | 0.15010 (18) | 0.23063 (16) | 0.65562 (16) | 0.0352 (6) | |
| O1W | 0.4156 (8) | 0.4621 (6) | 0.5274 (6) | 0.233 (7) | 0.5 |
| H1WB | 0.446348 | 0.427861 | 0.548992 | 0.350* | |
| H1WA | 0.422128 | 0.500970 | 0.570542 | 0.350* |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1A | 0.0391 (9) | 0.0421 (9) | 0.0293 (8) | −0.0029 (7) | 0.0034 (7) | 0.0068 (7) |
| N1A | 0.0339 (10) | 0.0331 (10) | 0.0263 (9) | 0.0033 (8) | 0.0075 (7) | 0.0065 (8) |
| N2A | 0.0289 (9) | 0.0430 (11) | 0.0268 (9) | 0.0059 (8) | 0.0097 (7) | 0.0084 (8) |
| N3A | 0.0286 (9) | 0.0367 (10) | 0.0244 (9) | 0.0050 (8) | 0.0076 (7) | 0.0058 (8) |
| N4A | 0.0331 (10) | 0.0386 (11) | 0.0252 (9) | 0.0063 (8) | 0.0075 (7) | 0.0037 (8) |
| N5A | 0.0362 (10) | 0.0338 (10) | 0.0271 (9) | 0.0057 (8) | 0.0079 (8) | 0.0041 (8) |
| N6A | 0.0445 (11) | 0.0343 (11) | 0.0326 (10) | 0.0085 (9) | 0.0070 (8) | 0.0075 (8) |
| C1A | 0.0355 (12) | 0.0333 (12) | 0.0317 (11) | 0.0055 (10) | 0.0075 (9) | 0.0099 (10) |
| C2A | 0.0391 (12) | 0.0349 (13) | 0.0290 (11) | 0.0024 (10) | 0.0076 (9) | 0.0110 (9) |
| C3A | 0.0448 (13) | 0.0422 (14) | 0.0328 (12) | 0.0086 (11) | 0.0085 (10) | 0.0147 (10) |
| C4A | 0.0454 (14) | 0.0510 (15) | 0.0277 (12) | 0.0017 (12) | 0.0024 (10) | 0.0149 (11) |
| C5A | 0.0476 (14) | 0.0467 (15) | 0.0264 (11) | 0.0025 (11) | 0.0107 (10) | 0.0089 (10) |
| C6A | 0.0419 (13) | 0.0415 (14) | 0.0281 (11) | 0.0035 (10) | 0.0121 (10) | 0.0082 (10) |
| C7A | 0.0339 (11) | 0.0385 (13) | 0.0272 (11) | 0.0011 (10) | 0.0098 (9) | 0.0109 (9) |
| C8A | 0.0296 (11) | 0.0376 (13) | 0.0275 (11) | 0.0026 (9) | 0.0097 (9) | 0.0086 (9) |
| C9A | 0.0254 (10) | 0.0391 (13) | 0.0273 (11) | 0.0043 (9) | 0.0081 (8) | 0.0063 (9) |
| C10A | 0.0259 (11) | 0.0409 (13) | 0.0282 (11) | 0.0073 (9) | 0.0068 (8) | 0.0071 (9) |
| C11A | 0.0315 (12) | 0.0448 (14) | 0.0343 (12) | 0.0109 (10) | 0.0081 (9) | 0.0061 (10) |
| C12A | 0.0440 (14) | 0.0437 (15) | 0.0459 (14) | 0.0162 (11) | 0.0111 (11) | 0.0131 (11) |
| C13A | 0.0501 (15) | 0.0488 (16) | 0.0442 (14) | 0.0140 (12) | 0.0139 (11) | 0.0213 (12) |
| C14A | 0.0371 (12) | 0.0502 (15) | 0.0313 (11) | 0.0100 (11) | 0.0091 (10) | 0.0136 (11) |
| C15A | 0.0266 (11) | 0.0401 (13) | 0.0288 (11) | 0.0076 (9) | 0.0071 (9) | 0.0086 (9) |
| C16A | 0.0280 (11) | 0.0413 (13) | 0.0250 (10) | 0.0042 (9) | 0.0064 (9) | 0.0066 (9) |
| C17A | 0.0366 (12) | 0.0337 (12) | 0.0257 (11) | 0.0035 (10) | 0.0077 (9) | 0.0023 (9) |
| C18A | 0.0376 (12) | 0.0291 (12) | 0.0323 (11) | 0.0033 (9) | 0.0097 (9) | −0.0011 (9) |
| C19A | 0.0420 (13) | 0.0306 (12) | 0.0361 (12) | 0.0022 (10) | 0.0129 (10) | −0.0001 (10) |
| C20A | 0.0409 (13) | 0.0341 (13) | 0.0448 (13) | 0.0019 (10) | 0.0172 (11) | −0.0036 (10) |
| C21A | 0.0366 (13) | 0.0345 (14) | 0.0530 (15) | 0.0048 (10) | 0.0139 (11) | −0.0044 (11) |
| C22A | 0.0426 (13) | 0.0329 (13) | 0.0433 (13) | 0.0090 (10) | 0.0065 (11) | −0.0011 (10) |
| C23A | 0.0381 (12) | 0.0311 (12) | 0.0347 (12) | 0.0052 (10) | 0.0084 (10) | −0.0005 (10) |
| C24A | 0.0385 (12) | 0.0295 (12) | 0.0344 (12) | 0.0075 (10) | 0.0054 (10) | 0.0048 (9) |
| C25A | 0.0462 (14) | 0.0421 (15) | 0.0363 (13) | −0.0023 (11) | −0.0013 (11) | 0.0042 (11) |
| C26A | 0.0450 (16) | 0.074 (2) | 0.0550 (17) | 0.0027 (14) | 0.0019 (13) | 0.0070 (15) |
| C27A | 0.0467 (15) | 0.0650 (19) | 0.0505 (16) | 0.0056 (14) | 0.0041 (12) | 0.0026 (14) |
| C28A | 0.0510 (17) | 0.079 (2) | 0.0650 (19) | 0.0185 (16) | 0.0009 (14) | −0.0013 (16) |
| C29A | 0.0570 (17) | 0.0544 (18) | 0.0496 (16) | 0.0091 (14) | 0.0032 (13) | 0.0014 (13) |
| C30A | 0.0557 (16) | 0.0491 (16) | 0.0465 (15) | 0.0113 (13) | 0.0056 (12) | 0.0058 (12) |
| C31A | 0.0606 (17) | 0.0399 (15) | 0.0387 (13) | 0.0072 (12) | 0.0065 (12) | 0.0071 (11) |
| C32A | 0.0542 (16) | 0.0409 (15) | 0.0439 (14) | 0.0072 (12) | 0.0080 (12) | 0.0064 (11) |
| B1A | 0.0360 (14) | 0.0372 (15) | 0.0268 (12) | 0.0032 (11) | 0.0071 (10) | 0.0072 (11) |
| N1B | 0.0358 (10) | 0.0241 (9) | 0.0266 (9) | 0.0043 (8) | 0.0087 (7) | 0.0058 (7) |
| N2B | 0.0347 (10) | 0.0282 (10) | 0.0326 (9) | 0.0052 (8) | 0.0109 (8) | 0.0067 (8) |
| N3B | 0.0341 (10) | 0.0252 (9) | 0.0301 (9) | 0.0036 (8) | 0.0082 (8) | 0.0052 (7) |
| N4B | 0.0396 (10) | 0.0274 (10) | 0.0323 (10) | 0.0063 (8) | 0.0085 (8) | 0.0049 (8) |
| N5B | 0.0363 (10) | 0.0270 (10) | 0.0279 (9) | 0.0062 (8) | 0.0072 (8) | 0.0060 (7) |
| N6B | 0.0374 (10) | 0.0300 (10) | 0.0256 (9) | 0.0059 (8) | 0.0060 (7) | 0.0059 (8) |
| C1B | 0.0352 (11) | 0.0295 (12) | 0.0232 (10) | 0.0033 (9) | 0.0086 (9) | 0.0077 (9) |
| C2B | 0.0396 (12) | 0.0278 (11) | 0.0233 (10) | 0.0035 (9) | 0.0127 (9) | 0.0059 (9) |
| C3B | 0.0409 (12) | 0.0323 (12) | 0.0258 (10) | 0.0001 (10) | 0.0128 (9) | 0.0058 (9) |
| C4B | 0.0543 (15) | 0.0279 (12) | 0.0305 (11) | −0.0023 (10) | 0.0184 (10) | 0.0047 (9) |
| C5B | 0.0551 (15) | 0.0268 (12) | 0.0348 (12) | 0.0085 (10) | 0.0186 (11) | 0.0092 (10) |
| C6B | 0.0452 (13) | 0.0307 (12) | 0.0301 (11) | 0.0089 (10) | 0.0146 (10) | 0.0100 (9) |
| C7B | 0.0409 (12) | 0.0275 (11) | 0.0238 (10) | 0.0051 (9) | 0.0132 (9) | 0.0067 (9) |
| C8B | 0.0340 (11) | 0.0297 (12) | 0.0282 (10) | 0.0068 (9) | 0.0120 (9) | 0.0092 (9) |
| C9B | 0.0314 (11) | 0.0285 (12) | 0.0343 (11) | 0.0041 (9) | 0.0096 (9) | 0.0100 (9) |
| C10B | 0.0335 (11) | 0.0285 (12) | 0.0331 (11) | −0.0010 (9) | 0.0084 (9) | 0.0082 (9) |
| C11B | 0.0350 (12) | 0.0323 (12) | 0.0399 (13) | 0.0007 (10) | 0.0079 (10) | 0.0117 (10) |
| C12B | 0.0424 (13) | 0.0386 (14) | 0.0374 (13) | 0.0005 (11) | 0.0031 (10) | 0.0141 (11) |
| C13B | 0.0469 (14) | 0.0400 (14) | 0.0304 (12) | −0.0037 (11) | 0.0059 (10) | 0.0091 (10) |
| C14B | 0.0407 (13) | 0.0320 (12) | 0.0358 (12) | 0.0002 (10) | 0.0096 (10) | 0.0063 (10) |
| C15B | 0.0340 (11) | 0.0287 (12) | 0.0322 (11) | −0.0008 (9) | 0.0086 (9) | 0.0075 (9) |
| C16B | 0.0374 (12) | 0.0244 (11) | 0.0329 (11) | 0.0009 (9) | 0.0098 (9) | 0.0051 (9) |
| C17B | 0.0407 (12) | 0.0242 (11) | 0.0298 (11) | 0.0056 (9) | 0.0094 (9) | 0.0048 (9) |
| C18B | 0.0383 (12) | 0.0326 (12) | 0.0324 (11) | 0.0106 (10) | 0.0083 (9) | 0.0083 (10) |
| C19B | 0.0495 (14) | 0.0365 (13) | 0.0377 (12) | 0.0120 (11) | 0.0125 (11) | 0.0063 (10) |
| C20B | 0.0495 (15) | 0.0481 (16) | 0.0481 (14) | 0.0190 (12) | 0.0206 (12) | 0.0099 (12) |
| C21B | 0.0398 (13) | 0.0523 (16) | 0.0523 (15) | 0.0140 (12) | 0.0153 (12) | 0.0133 (13) |
| C22B | 0.0389 (13) | 0.0408 (14) | 0.0414 (13) | 0.0085 (11) | 0.0093 (10) | 0.0084 (11) |
| C23B | 0.0384 (12) | 0.0347 (13) | 0.0335 (11) | 0.0108 (10) | 0.0089 (10) | 0.0104 (10) |
| C24B | 0.0360 (12) | 0.0310 (12) | 0.0266 (10) | 0.0064 (9) | 0.0063 (9) | 0.0072 (9) |
| O1B | 0.0454 (9) | 0.0290 (8) | 0.0345 (8) | 0.0013 (7) | 0.0139 (7) | 0.0089 (6) |
| C25B | 0.0540 (14) | 0.0303 (12) | 0.0479 (13) | 0.0027 (11) | 0.0158 (11) | 0.0133 (10) |
| C26B | 0.0606 (16) | 0.0530 (16) | 0.0702 (17) | −0.0051 (13) | 0.0128 (14) | 0.0197 (14) |
| C27B | 0.062 (2) | 0.067 (3) | 0.069 (2) | 0.001 (2) | 0.021 (2) | 0.031 (2) |
| C28B | 0.064 (3) | 0.096 (3) | 0.105 (4) | 0.006 (2) | 0.023 (3) | 0.032 (3) |
| C29B | 0.080 (3) | 0.105 (4) | 0.114 (4) | 0.005 (3) | 0.017 (3) | 0.027 (3) |
| C30B | 0.089 (3) | 0.136 (3) | 0.136 (3) | 0.002 (2) | −0.004 (2) | 0.019 (3) |
| C31B | 0.078 (3) | 0.111 (4) | 0.084 (3) | 0.033 (3) | 0.020 (3) | 0.004 (3) |
| C32B | 0.150 (5) | 0.150 (5) | 0.130 (4) | 0.052 (4) | 0.028 (4) | 0.037 (4) |
| C25D | 0.0540 (14) | 0.0303 (12) | 0.0479 (13) | 0.0027 (11) | 0.0158 (11) | 0.0133 (10) |
| C26D | 0.0606 (16) | 0.0530 (16) | 0.0702 (17) | −0.0051 (13) | 0.0128 (14) | 0.0197 (14) |
| C27D | 0.064 (4) | 0.076 (4) | 0.089 (5) | 0.008 (4) | 0.026 (4) | 0.025 (4) |
| C28D | 0.065 (4) | 0.093 (5) | 0.092 (5) | 0.009 (4) | 0.012 (4) | 0.037 (5) |
| C29D | 0.074 (4) | 0.116 (5) | 0.099 (5) | 0.017 (4) | 0.013 (4) | 0.030 (4) |
| C30D | 0.089 (3) | 0.136 (3) | 0.136 (3) | 0.002 (2) | −0.004 (2) | 0.019 (3) |
| C31D | 0.109 (5) | 0.133 (6) | 0.119 (6) | 0.017 (5) | 0.018 (5) | 0.027 (5) |
| C32D | 0.150 (5) | 0.150 (5) | 0.130 (4) | 0.052 (4) | 0.028 (4) | 0.037 (4) |
| B1B | 0.0367 (13) | 0.0266 (13) | 0.0294 (12) | 0.0051 (10) | 0.0087 (10) | 0.0065 (10) |
| N1C | 0.0340 (10) | 0.0291 (10) | 0.0269 (9) | 0.0103 (8) | 0.0019 (7) | 0.0030 (7) |
| N2C | 0.0341 (10) | 0.0388 (11) | 0.0258 (9) | 0.0145 (8) | 0.0049 (8) | 0.0042 (8) |
| N3C | 0.0338 (10) | 0.0286 (10) | 0.0270 (9) | 0.0084 (8) | 0.0032 (7) | 0.0079 (7) |
| N4C | 0.0350 (10) | 0.0379 (11) | 0.0307 (9) | 0.0020 (8) | 0.0062 (8) | 0.0149 (8) |
| N5C | 0.0336 (10) | 0.0303 (10) | 0.0299 (9) | 0.0011 (8) | 0.0020 (8) | 0.0099 (8) |
| N6C | 0.0330 (10) | 0.0283 (10) | 0.0300 (9) | 0.0028 (8) | 0.0024 (7) | 0.0048 (8) |
| C1C | 0.0333 (12) | 0.0276 (11) | 0.0270 (11) | 0.0075 (9) | 0.0016 (9) | 0.0010 (9) |
| C2C | 0.0368 (12) | 0.0338 (12) | 0.0256 (10) | 0.0104 (10) | 0.0059 (9) | 0.0006 (9) |
| C3C | 0.0412 (13) | 0.0464 (14) | 0.0254 (11) | 0.0109 (11) | 0.0039 (10) | 0.0031 (10) |
| C4C | 0.0506 (15) | 0.0702 (19) | 0.0267 (12) | 0.0122 (13) | 0.0080 (11) | 0.0119 (12) |
| C5C | 0.0474 (15) | 0.083 (2) | 0.0323 (13) | 0.0091 (14) | 0.0138 (11) | 0.0140 (13) |
| C6C | 0.0380 (13) | 0.0658 (18) | 0.0301 (12) | 0.0106 (12) | 0.0071 (10) | 0.0040 (11) |
| C7C | 0.0357 (12) | 0.0433 (14) | 0.0250 (11) | 0.0141 (10) | 0.0067 (9) | 0.0014 (10) |
| C8C | 0.0341 (12) | 0.0346 (12) | 0.0286 (11) | 0.0142 (10) | 0.0061 (9) | 0.0024 (9) |
| C9C | 0.0330 (12) | 0.0282 (11) | 0.0297 (11) | 0.0125 (9) | 0.0055 (9) | 0.0064 (9) |
| C10C | 0.0335 (11) | 0.0264 (11) | 0.0270 (10) | 0.0115 (9) | 0.0048 (9) | 0.0078 (9) |
| C11C | 0.0335 (11) | 0.0307 (12) | 0.0306 (11) | 0.0100 (9) | 0.0078 (9) | 0.0080 (9) |
| C12C | 0.0338 (12) | 0.0297 (12) | 0.0319 (11) | 0.0068 (9) | 0.0047 (9) | 0.0028 (9) |
| C13C | 0.0401 (12) | 0.0299 (12) | 0.0285 (11) | 0.0068 (10) | 0.0053 (9) | 0.0021 (9) |
| C14C | 0.0401 (13) | 0.0351 (13) | 0.0278 (11) | 0.0095 (10) | 0.0088 (9) | 0.0080 (9) |
| C15C | 0.0350 (11) | 0.0271 (11) | 0.0278 (11) | 0.0078 (9) | 0.0056 (9) | 0.0092 (9) |
| C16C | 0.0377 (12) | 0.0283 (12) | 0.0284 (11) | 0.0054 (9) | 0.0057 (9) | 0.0116 (9) |
| C17C | 0.0372 (12) | 0.0329 (12) | 0.0326 (12) | −0.0007 (10) | 0.0068 (9) | 0.0134 (10) |
| C18C | 0.0312 (12) | 0.0389 (13) | 0.0360 (12) | −0.0033 (10) | 0.0063 (9) | 0.0137 (10) |
| C19C | 0.0370 (13) | 0.0514 (15) | 0.0350 (12) | −0.0059 (11) | 0.0094 (10) | 0.0131 (11) |
| C20C | 0.0346 (13) | 0.0526 (16) | 0.0435 (14) | −0.0029 (11) | 0.0130 (11) | 0.0104 (12) |
| C21C | 0.0292 (12) | 0.0470 (15) | 0.0444 (13) | −0.0006 (10) | 0.0085 (10) | 0.0135 (11) |
| C22C | 0.0304 (11) | 0.0377 (13) | 0.0364 (12) | −0.0019 (10) | 0.0034 (9) | 0.0102 (10) |
| C23C | 0.0313 (11) | 0.0332 (12) | 0.0330 (11) | −0.0021 (9) | 0.0048 (9) | 0.0104 (9) |
| C24C | 0.0322 (11) | 0.0276 (12) | 0.0312 (11) | −0.0002 (9) | 0.0008 (9) | 0.0064 (9) |
| O1C | 0.0783 (13) | 0.0281 (9) | 0.0611 (11) | 0.0053 (9) | −0.0238 (10) | 0.0099 (8) |
| C25C | 0.048 (2) | 0.039 (2) | 0.054 (3) | 0.007 (2) | 0.014 (2) | 0.015 (2) |
| C26C | 0.044 (3) | 0.035 (2) | 0.060 (3) | 0.005 (2) | 0.014 (2) | 0.020 (2) |
| C27C | 0.049 (3) | 0.040 (3) | 0.065 (3) | 0.005 (2) | 0.017 (2) | 0.020 (2) |
| C28C | 0.055 (3) | 0.044 (4) | 0.068 (3) | 0.010 (3) | 0.017 (3) | 0.025 (4) |
| C29C | 0.059 (3) | 0.047 (3) | 0.079 (3) | 0.010 (2) | 0.024 (2) | 0.029 (3) |
| C30C | 0.064 (3) | 0.056 (3) | 0.088 (3) | 0.018 (3) | 0.031 (3) | 0.039 (3) |
| C31C | 0.076 (4) | 0.070 (4) | 0.118 (5) | 0.023 (3) | 0.042 (4) | 0.050 (4) |
| C32C | 0.097 (8) | 0.106 (7) | 0.158 (9) | −0.020 (6) | 0.004 (7) | 0.068 (7) |
| O1E | 0.0783 (13) | 0.0281 (9) | 0.0611 (11) | 0.0053 (9) | −0.0238 (10) | 0.0099 (8) |
| C25E | 0.041 (2) | 0.031 (2) | 0.053 (2) | 0.0106 (19) | 0.016 (2) | 0.0133 (19) |
| C26E | 0.035 (3) | 0.033 (2) | 0.052 (3) | 0.011 (2) | 0.014 (2) | 0.015 (2) |
| C27E | 0.047 (3) | 0.035 (3) | 0.061 (3) | 0.012 (2) | 0.021 (2) | 0.017 (2) |
| C28E | 0.059 (3) | 0.040 (3) | 0.065 (4) | 0.014 (3) | 0.021 (3) | 0.029 (3) |
| C29E | 0.072 (3) | 0.050 (3) | 0.073 (3) | 0.018 (3) | 0.029 (3) | 0.025 (3) |
| C30E | 0.068 (3) | 0.066 (3) | 0.104 (4) | 0.020 (3) | 0.023 (3) | 0.040 (3) |
| C31E | 0.076 (5) | 0.065 (4) | 0.101 (5) | 0.027 (4) | 0.027 (4) | 0.050 (4) |
| C32E | 0.143 (11) | 0.093 (8) | 0.135 (10) | 0.036 (8) | 0.039 (8) | 0.047 (7) |
| B1C | 0.0384 (14) | 0.0281 (14) | 0.0323 (13) | 0.0072 (11) | −0.0004 (11) | 0.0065 (11) |
| O1W | 0.269 (12) | 0.168 (9) | 0.182 (9) | 0.155 (9) | −0.043 (8) | −0.022 (7) |
Geometric parameters (Å, º) top
| O1A—B1A | 1.416 (3) | C28B—H28D | 0.9900 |
| O1A—C25A | 1.429 (3) | C29B—C30B | 1.568 (6) |
| N1A—C1A | 1.362 (3) | C29B—H29C | 0.9900 |
| N1A—C8A | 1.367 (3) | C29B—H29D | 0.9900 |
| N1A—B1A | 1.503 (3) | C30B—C31B | 1.553 (6) |
| N2A—C8A | 1.342 (3) | C30B—H30C | 0.9900 |
| N2A—C9A | 1.347 (3) | C30B—H30D | 0.9900 |
| N3A—C9A | 1.368 (3) | C31B—C32B | 1.484 (6) |
| N3A—C16A | 1.371 (3) | C31B—H31C | 0.9900 |
| N3A—B1A | 1.510 (3) | C31B—H31D | 0.9900 |
| N4A—C17A | 1.343 (3) | C32B—H32D | 0.9800 |
| N4A—C16A | 1.352 (3) | C32B—H32E | 0.9800 |
| N5A—C24A | 1.362 (3) | C32B—H32F | 0.9800 |
| N5A—C17A | 1.372 (3) | C25D—C26D | 1.511 (4) |
| N5A—B1A | 1.508 (3) | C25D—H25E | 0.9900 |
| N6A—C1A | 1.342 (3) | C25D—H25F | 0.9900 |
| N6A—C24A | 1.347 (3) | C26D—C27D | 1.447 (9) |
| C1A—C2A | 1.457 (3) | C26D—H26E | 0.9900 |
| C2A—C3A | 1.394 (3) | C26D—H26F | 0.9900 |
| C2A—C7A | 1.419 (3) | C27D—C28D | 1.557 (10) |
| C3A—C4A | 1.384 (4) | C27D—H27E | 0.9900 |
| C3A—H3AA | 0.9500 | C27D—H27F | 0.9900 |
| C4A—C5A | 1.393 (4) | C28D—C29D | 1.573 (10) |
| C4A—H4AA | 0.9500 | C28D—H28E | 0.9900 |
| C5A—C6A | 1.382 (3) | C28D—H28F | 0.9900 |
| C5A—H5AA | 0.9500 | C29D—C30D | 1.544 (10) |
| C6A—C7A | 1.393 (3) | C29D—H29E | 0.9900 |
| C6A—H6AA | 0.9500 | C29D—H29F | 0.9900 |
| C7A—C8A | 1.456 (3) | C30D—C31D | 1.511 (10) |
| C9A—C10A | 1.450 (3) | C30D—H30E | 0.9900 |
| C10A—C11A | 1.397 (3) | C30D—H30F | 0.9900 |
| C10A—C15A | 1.422 (3) | C31D—C32D | 1.462 (10) |
| C11A—C12A | 1.378 (4) | C31D—H31E | 0.9900 |
| C11A—H11A | 0.9500 | C31D—H31F | 0.9900 |
| C12A—C13A | 1.403 (4) | C32D—H32M | 0.9800 |
| C12A—H12A | 0.9500 | C32D—H32N | 0.9800 |
| C13A—C14A | 1.379 (4) | C32D—H32O | 0.9800 |
| C13A—H13A | 0.9500 | N1C—C8C | 1.367 (3) |
| C14A—C15A | 1.397 (3) | N1C—C1C | 1.369 (3) |
| C14A—H14A | 0.9500 | N1C—B1C | 1.500 (3) |
| C15A—C16A | 1.449 (3) | N2C—C8C | 1.347 (3) |
| C17A—C18A | 1.454 (3) | N2C—C9C | 1.347 (3) |
| C18A—C19A | 1.396 (3) | N3C—C16C | 1.365 (3) |
| C18A—C23A | 1.419 (3) | N3C—C9C | 1.369 (3) |
| C19A—C20A | 1.382 (3) | N3C—B1C | 1.507 (3) |
| C19A—H19A | 0.9500 | N4C—C16C | 1.346 (3) |
| C20A—C21A | 1.396 (4) | N4C—C17C | 1.347 (3) |
| C20A—H20A | 0.9500 | N5C—C24C | 1.363 (3) |
| C21A—C22A | 1.384 (4) | N5C—C17C | 1.366 (3) |
| C21A—H21A | 0.9500 | N5C—B1C | 1.496 (3) |
| C22A—C23A | 1.393 (3) | N6C—C24C | 1.348 (3) |
| C22A—H22A | 0.9500 | N6C—C1C | 1.349 (3) |
| C23A—C24A | 1.460 (3) | C1C—C2C | 1.447 (3) |
| C25A—C26A | 1.475 (4) | C2C—C3C | 1.397 (3) |
| C25A—H25A | 0.9900 | C2C—C7C | 1.428 (3) |
| C25A—H25B | 0.9900 | C3C—C4C | 1.380 (4) |
| C26A—C27A | 1.537 (4) | C3C—H3CA | 0.9500 |
| C26A—H26A | 0.9900 | C4C—C5C | 1.397 (4) |
| C26A—H26B | 0.9900 | C4C—H4CA | 0.9500 |
| C27A—C28A | 1.497 (4) | C5C—C6C | 1.386 (4) |
| C27A—H27A | 0.9900 | C5C—H5CA | 0.9500 |
| C27A—H27B | 0.9900 | C6C—C7C | 1.393 (4) |
| C28A—C29A | 1.520 (4) | C6C—H6CA | 0.9500 |
| C28A—H28A | 0.9900 | C7C—C8C | 1.457 (3) |
| C28A—H28B | 0.9900 | C9C—C10C | 1.463 (3) |
| C29A—C30A | 1.502 (4) | C10C—C11C | 1.396 (3) |
| C29A—H29A | 0.9900 | C10C—C15C | 1.424 (3) |
| C29A—H29B | 0.9900 | C11C—C12C | 1.387 (3) |
| C30A—C31A | 1.515 (4) | C11C—H11B | 0.9500 |
| C30A—H30A | 0.9900 | C12C—C13C | 1.394 (3) |
| C30A—H30B | 0.9900 | C12C—H12B | 0.9500 |
| C31A—C32A | 1.510 (4) | C13C—C14C | 1.385 (3) |
| C31A—H31A | 0.9900 | C13C—H13B | 0.9500 |
| C31A—H31B | 0.9900 | C14C—C15C | 1.393 (3) |
| C32A—H32A | 0.9800 | C14C—H14B | 0.9500 |
| C32A—H32B | 0.9800 | C15C—C16C | 1.456 (3) |
| C32A—H32C | 0.9800 | C17C—C18C | 1.456 (3) |
| N1B—C8B | 1.363 (3) | C18C—C19C | 1.388 (4) |
| N1B—C1B | 1.364 (3) | C18C—C23C | 1.427 (3) |
| N1B—B1B | 1.501 (3) | C19C—C20C | 1.384 (3) |
| N2B—C8B | 1.343 (3) | C19C—H19B | 0.9500 |
| N2B—C9B | 1.346 (3) | C20C—C21C | 1.397 (3) |
| N3B—C9B | 1.367 (3) | C20C—H20B | 0.9500 |
| N3B—C16B | 1.375 (3) | C21C—C22C | 1.387 (3) |
| N3B—B1B | 1.506 (3) | C21C—H21B | 0.9500 |
| N4B—C16B | 1.340 (3) | C22C—C23C | 1.390 (3) |
| N4B—C17B | 1.347 (3) | C22C—H22B | 0.9500 |
| N5B—C17B | 1.368 (3) | C23C—C24C | 1.457 (3) |
| N5B—C24B | 1.368 (3) | O1C—C25C | 1.274 (4) |
| N5B—B1B | 1.504 (3) | O1C—B1C | 1.406 (3) |
| N6B—C1B | 1.346 (3) | C25C—C26C | 1.494 (5) |
| N6B—C24B | 1.350 (3) | C25C—H25G | 0.9900 |
| C1B—C2B | 1.456 (3) | C25C—H25H | 0.9900 |
| C2B—C3B | 1.395 (3) | C26C—C27C | 1.510 (6) |
| C2B—C7B | 1.418 (3) | C26C—H26G | 0.9900 |
| C3B—C4B | 1.385 (3) | C26C—H26H | 0.9900 |
| C3B—H3BA | 0.9500 | C27C—C28C | 1.520 (6) |
| C4B—C5B | 1.395 (3) | C27C—H27G | 0.9900 |
| C4B—H4BA | 0.9500 | C27C—H27H | 0.9900 |
| C5B—C6B | 1.384 (3) | C28C—C29C | 1.520 (6) |
| C5B—H5BA | 0.9500 | C28C—H28G | 0.9900 |
| C6B—C7B | 1.389 (3) | C28C—H28H | 0.9900 |
| C6B—H6BA | 0.9500 | C29C—C30C | 1.527 (6) |
| C7B—C8B | 1.455 (3) | C29C—H29G | 0.9900 |
| C9B—C10B | 1.458 (3) | C29C—H29H | 0.9900 |
| C10B—C11B | 1.393 (3) | C30C—C31C | 1.517 (6) |
| C10B—C15B | 1.416 (3) | C30C—H30G | 0.9900 |
| C11B—C12B | 1.384 (3) | C30C—H30H | 0.9900 |
| C11B—H11C | 0.9500 | C31C—C32C | 1.518 (8) |
| C12B—C13B | 1.399 (4) | C31C—H31G | 0.9900 |
| C12B—H12C | 0.9500 | C31C—H31H | 0.9900 |
| C13B—C14B | 1.378 (3) | C32C—H32G | 0.9800 |
| C13B—H13C | 0.9500 | C32C—H32H | 0.9800 |
| C14B—C15B | 1.393 (3) | C32C—H32I | 0.9800 |
| C14B—H14C | 0.9500 | O1E—C25E | 1.276 (4) |
| C15B—C16B | 1.450 (3) | O1E—B1C | 1.406 (3) |
| C17B—C18B | 1.452 (3) | C25E—C26E | 1.484 (6) |
| C18B—C19B | 1.390 (3) | C25E—H25J | 0.9900 |
| C18B—C23B | 1.423 (3) | C25E—H25K | 0.9900 |
| C19B—C20B | 1.386 (4) | C26E—C27E | 1.516 (7) |
| C19B—H19C | 0.9500 | C26E—H26J | 0.9900 |
| C20B—C21B | 1.393 (4) | C26E—H26K | 0.9900 |
| C20B—H20C | 0.9500 | C27E—C28E | 1.517 (8) |
| C21B—C22B | 1.380 (4) | C27E—H27J | 0.9900 |
| C21B—H21C | 0.9500 | C27E—H27K | 0.9900 |
| C22B—C23B | 1.392 (3) | C28E—C29E | 1.523 (8) |
| C22B—H22C | 0.9500 | C28E—H28J | 0.9900 |
| C23B—C24B | 1.461 (3) | C28E—H28K | 0.9900 |
| O1B—B1B | 1.421 (3) | C29E—C30E | 1.505 (7) |
| O1B—C25B | 1.429 (3) | C29E—H29J | 0.9900 |
| O1B—C25D | 1.429 (3) | C29E—H29K | 0.9900 |
| C25B—C26B | 1.511 (4) | C30E—C31E | 1.540 (8) |
| C25B—H25C | 0.9900 | C30E—H30J | 0.9900 |
| C25B—H25D | 0.9900 | C30E—H30K | 0.9900 |
| C26B—C27B | 1.503 (5) | C31E—C32E | 1.545 (10) |
| C26B—H26C | 0.9900 | C31E—H31J | 0.9900 |
| C26B—H26D | 0.9900 | C31E—H31K | 0.9900 |
| C27B—C28B | 1.536 (5) | C32E—H32J | 0.9800 |
| C27B—H27C | 0.9900 | C32E—H32K | 0.9800 |
| C27B—H27D | 0.9900 | C32E—H32L | 0.9800 |
| C28B—C29B | 1.516 (6) | O1W—H1WB | 0.8400 |
| C28B—H28C | 0.9900 | O1W—H1WA | 0.8400 |
| B1A—O1A—C25A | 117.29 (18) | H30C—C30B—H30D | 108.6 |
| C1A—N1A—C8A | 112.41 (17) | C32B—C31B—C30B | 109.4 (5) |
| C1A—N1A—B1A | 123.00 (19) | C32B—C31B—H31C | 109.8 |
| C8A—N1A—B1A | 123.16 (18) | C30B—C31B—H31C | 109.8 |
| C8A—N2A—C9A | 117.18 (19) | C32B—C31B—H31D | 109.8 |
| C9A—N3A—C16A | 112.27 (18) | C30B—C31B—H31D | 109.8 |
| C9A—N3A—B1A | 122.79 (18) | H31C—C31B—H31D | 108.2 |
| C16A—N3A—B1A | 123.52 (18) | C31B—C32B—H32D | 109.5 |
| C17A—N4A—C16A | 116.72 (18) | C31B—C32B—H32E | 109.5 |
| C24A—N5A—C17A | 112.40 (19) | H32D—C32B—H32E | 109.5 |
| C24A—N5A—B1A | 122.71 (18) | C31B—C32B—H32F | 109.5 |
| C17A—N5A—B1A | 123.86 (18) | H32D—C32B—H32F | 109.5 |
| C1A—N6A—C24A | 116.90 (19) | H32E—C32B—H32F | 109.5 |
| N6A—C1A—N1A | 122.66 (19) | O1B—C25D—C26D | 110.4 (2) |
| N6A—C1A—C2A | 129.0 (2) | O1B—C25D—H25E | 109.6 |
| N1A—C1A—C2A | 106.23 (19) | C26D—C25D—H25E | 109.6 |
| C3A—C2A—C7A | 120.4 (2) | O1B—C25D—H25F | 109.6 |
| C3A—C2A—C1A | 132.1 (2) | C26D—C25D—H25F | 109.6 |
| C7A—C2A—C1A | 107.01 (18) | H25E—C25D—H25F | 108.1 |
| C4A—C3A—C2A | 118.0 (2) | C27D—C26D—C25D | 120.4 (5) |
| C4A—C3A—H3AA | 121.0 | C27D—C26D—H26E | 107.2 |
| C2A—C3A—H3AA | 121.0 | C25D—C26D—H26E | 107.2 |
| C3A—C4A—C5A | 121.4 (2) | C27D—C26D—H26F | 107.2 |
| C3A—C4A—H4AA | 119.3 | C25D—C26D—H26F | 107.2 |
| C5A—C4A—H4AA | 119.3 | H26E—C26D—H26F | 106.9 |
| C6A—C5A—C4A | 121.5 (2) | C26D—C27D—C28D | 114.8 (9) |
| C6A—C5A—H5AA | 119.3 | C26D—C27D—H27E | 108.6 |
| C4A—C5A—H5AA | 119.3 | C28D—C27D—H27E | 108.6 |
| C5A—C6A—C7A | 118.0 (2) | C26D—C27D—H27F | 108.6 |
| C5A—C6A—H6AA | 121.0 | C28D—C27D—H27F | 108.6 |
| C7A—C6A—H6AA | 121.0 | H27E—C27D—H27F | 107.5 |
| C6A—C7A—C2A | 120.6 (2) | C27D—C28D—C29D | 104.7 (8) |
| C6A—C7A—C8A | 132.0 (2) | C27D—C28D—H28E | 110.8 |
| C2A—C7A—C8A | 106.88 (19) | C29D—C28D—H28E | 110.8 |
| N2A—C8A—N1A | 122.72 (18) | C27D—C28D—H28F | 110.8 |
| N2A—C8A—C7A | 128.9 (2) | C29D—C28D—H28F | 110.8 |
| N1A—C8A—C7A | 106.27 (18) | H28E—C28D—H28F | 108.9 |
| N2A—C9A—N3A | 122.64 (19) | C30D—C29D—C28D | 101.8 (9) |
| N2A—C9A—C10A | 128.9 (2) | C30D—C29D—H29E | 111.4 |
| N3A—C9A—C10A | 106.25 (18) | C28D—C29D—H29E | 111.4 |
| C11A—C10A—C15A | 120.7 (2) | C30D—C29D—H29F | 111.4 |
| C11A—C10A—C9A | 132.1 (2) | C28D—C29D—H29F | 111.4 |
| C15A—C10A—C9A | 106.94 (19) | H29E—C29D—H29F | 109.3 |
| C12A—C11A—C10A | 118.0 (2) | C31D—C30D—C29D | 110.1 (9) |
| C12A—C11A—H11A | 121.0 | C31D—C30D—H30E | 109.6 |
| C10A—C11A—H11A | 121.0 | C29D—C30D—H30E | 109.6 |
| C11A—C12A—C13A | 121.5 (2) | C31D—C30D—H30F | 109.6 |
| C11A—C12A—H12A | 119.2 | C29D—C30D—H30F | 109.6 |
| C13A—C12A—H12A | 119.2 | H30E—C30D—H30F | 108.1 |
| C14A—C13A—C12A | 121.3 (2) | C32D—C31D—C30D | 113.0 (8) |
| C14A—C13A—H13A | 119.4 | C32D—C31D—H31E | 109.0 |
| C12A—C13A—H13A | 119.4 | C30D—C31D—H31E | 109.0 |
| C13A—C14A—C15A | 118.3 (2) | C32D—C31D—H31F | 109.0 |
| C13A—C14A—H14A | 120.9 | C30D—C31D—H31F | 109.0 |
| C15A—C14A—H14A | 120.9 | H31E—C31D—H31F | 107.8 |
| C14A—C15A—C10A | 120.3 (2) | C31D—C32D—H32M | 109.5 |
| C14A—C15A—C16A | 132.1 (2) | C31D—C32D—H32N | 109.5 |
| C10A—C15A—C16A | 107.21 (18) | H32M—C32D—H32N | 109.5 |
| N4A—C16A—N3A | 122.7 (2) | C31D—C32D—H32O | 109.5 |
| N4A—C16A—C15A | 129.2 (2) | H32M—C32D—H32O | 109.5 |
| N3A—C16A—C15A | 106.07 (18) | H32N—C32D—H32O | 109.5 |
| N4A—C17A—N5A | 122.4 (2) | O1B—B1B—N1B | 110.72 (18) |
| N4A—C17A—C18A | 129.7 (2) | O1B—B1B—N5B | 117.42 (19) |
| N5A—C17A—C18A | 106.05 (18) | N1B—B1B—N5B | 102.59 (18) |
| C19A—C18A—C23A | 120.6 (2) | O1B—B1B—N3B | 118.1 (2) |
| C19A—C18A—C17A | 132.0 (2) | N1B—B1B—N3B | 103.49 (17) |
| C23A—C18A—C17A | 107.2 (2) | N5B—B1B—N3B | 102.61 (18) |
| C20A—C19A—C18A | 117.6 (2) | C8C—N1C—C1C | 112.88 (19) |
| C20A—C19A—H19A | 121.2 | C8C—N1C—B1C | 123.24 (18) |
| C18A—C19A—H19A | 121.2 | C1C—N1C—B1C | 122.78 (19) |
| C19A—C20A—C21A | 121.8 (2) | C8C—N2C—C9C | 116.7 (2) |
| C19A—C20A—H20A | 119.1 | C16C—N3C—C9C | 113.21 (18) |
| C21A—C20A—H20A | 119.1 | C16C—N3C—B1C | 122.8 (2) |
| C22A—C21A—C20A | 121.4 (2) | C9C—N3C—B1C | 123.29 (19) |
| C22A—C21A—H21A | 119.3 | C16C—N4C—C17C | 116.72 (19) |
| C20A—C21A—H21A | 119.3 | C24C—N5C—C17C | 113.03 (19) |
| C21A—C22A—C23A | 117.7 (2) | C24C—N5C—B1C | 123.58 (19) |
| C21A—C22A—H22A | 121.2 | C17C—N5C—B1C | 122.65 (18) |
| C23A—C22A—H22A | 121.2 | C24C—N6C—C1C | 117.39 (17) |
| C22A—C23A—C18A | 120.9 (2) | N6C—C1C—N1C | 122.3 (2) |
| C22A—C23A—C24A | 131.8 (2) | N6C—C1C—C2C | 130.14 (19) |
| C18A—C23A—C24A | 106.92 (19) | N1C—C1C—C2C | 105.85 (19) |
| N6A—C24A—N5A | 122.7 (2) | C3C—C2C—C7C | 120.5 (2) |
| N6A—C24A—C23A | 129.5 (2) | C3C—C2C—C1C | 132.3 (2) |
| N5A—C24A—C23A | 106.23 (19) | C7C—C2C—C1C | 107.12 (18) |
| O1A—C25A—C26A | 111.6 (2) | C4C—C3C—C2C | 117.7 (2) |
| O1A—C25A—H25A | 109.3 | C4C—C3C—H3CA | 121.1 |
| C26A—C25A—H25A | 109.3 | C2C—C3C—H3CA | 121.1 |
| O1A—C25A—H25B | 109.3 | C3C—C4C—C5C | 121.8 (2) |
| C26A—C25A—H25B | 109.3 | C3C—C4C—H4CA | 119.1 |
| H25A—C25A—H25B | 108.0 | C5C—C4C—H4CA | 119.1 |
| C25A—C26A—C27A | 111.7 (2) | C6C—C5C—C4C | 121.5 (3) |
| C25A—C26A—H26A | 109.3 | C6C—C5C—H5CA | 119.3 |
| C27A—C26A—H26A | 109.3 | C4C—C5C—H5CA | 119.3 |
| C25A—C26A—H26B | 109.3 | C5C—C6C—C7C | 117.8 (2) |
| C27A—C26A—H26B | 109.3 | C5C—C6C—H6CA | 121.1 |
| H26A—C26A—H26B | 107.9 | C7C—C6C—H6CA | 121.1 |
| C28A—C27A—C26A | 113.4 (3) | C6C—C7C—C2C | 120.7 (2) |
| C28A—C27A—H27A | 108.9 | C6C—C7C—C8C | 132.2 (2) |
| C26A—C27A—H27A | 108.9 | C2C—C7C—C8C | 107.0 (2) |
| C28A—C27A—H27B | 108.9 | N2C—C8C—N1C | 122.8 (2) |
| C26A—C27A—H27B | 108.9 | N2C—C8C—C7C | 130.1 (2) |
| H27A—C27A—H27B | 107.7 | N1C—C8C—C7C | 105.51 (18) |
| C27A—C28A—C29A | 114.1 (3) | N2C—C9C—N3C | 122.52 (18) |
| C27A—C28A—H28A | 108.7 | N2C—C9C—C10C | 131.0 (2) |
| C29A—C28A—H28A | 108.7 | N3C—C9C—C10C | 105.31 (18) |
| C27A—C28A—H28B | 108.7 | C11C—C10C—C15C | 120.49 (19) |
| C29A—C28A—H28B | 108.7 | C11C—C10C—C9C | 132.2 (2) |
| H28A—C28A—H28B | 107.6 | C15C—C10C—C9C | 107.25 (19) |
| C30A—C29A—C28A | 112.6 (2) | C12C—C11C—C10C | 117.6 (2) |
| C30A—C29A—H29A | 109.1 | C12C—C11C—H11B | 121.2 |
| C28A—C29A—H29A | 109.1 | C10C—C11C—H11B | 121.2 |
| C30A—C29A—H29B | 109.1 | C11C—C12C—C13C | 121.8 (2) |
| C28A—C29A—H29B | 109.1 | C11C—C12C—H12B | 119.1 |
| H29A—C29A—H29B | 107.8 | C13C—C12C—H12B | 119.1 |
| C29A—C30A—C31A | 114.0 (2) | C14C—C13C—C12C | 121.2 (2) |
| C29A—C30A—H30A | 108.7 | C14C—C13C—H13B | 119.4 |
| C31A—C30A—H30A | 108.7 | C12C—C13C—H13B | 119.4 |
| C29A—C30A—H30B | 108.7 | C13C—C14C—C15C | 118.0 (2) |
| C31A—C30A—H30B | 108.7 | C13C—C14C—H14B | 121.0 |
| H30A—C30A—H30B | 107.6 | C15C—C14C—H14B | 121.0 |
| C32A—C31A—C30A | 112.9 (2) | C14C—C15C—C10C | 120.7 (2) |
| C32A—C31A—H31A | 109.0 | C14C—C15C—C16C | 132.3 (2) |
| C30A—C31A—H31A | 109.0 | C10C—C15C—C16C | 106.97 (18) |
| C32A—C31A—H31B | 109.0 | N4C—C16C—N3C | 122.39 (19) |
| C30A—C31A—H31B | 109.0 | N4C—C16C—C15C | 130.6 (2) |
| H31A—C31A—H31B | 107.8 | N3C—C16C—C15C | 105.83 (19) |
| C31A—C32A—H32A | 109.5 | N4C—C17C—N5C | 122.6 (2) |
| C31A—C32A—H32B | 109.5 | N4C—C17C—C18C | 130.0 (2) |
| H32A—C32A—H32B | 109.5 | N5C—C17C—C18C | 105.88 (18) |
| C31A—C32A—H32C | 109.5 | C19C—C18C—C23C | 120.7 (2) |
| H32A—C32A—H32C | 109.5 | C19C—C18C—C17C | 132.5 (2) |
| H32B—C32A—H32C | 109.5 | C23C—C18C—C17C | 106.8 (2) |
| O1A—B1A—N1A | 111.98 (19) | C20C—C19C—C18C | 118.3 (2) |
| O1A—B1A—N5A | 116.5 (2) | C20C—C19C—H19B | 120.8 |
| N1A—B1A—N5A | 103.26 (18) | C18C—C19C—H19B | 120.8 |
| O1A—B1A—N3A | 117.28 (19) | C19C—C20C—C21C | 120.9 (2) |
| N1A—B1A—N3A | 103.62 (18) | C19C—C20C—H20B | 119.5 |
| N5A—B1A—N3A | 102.45 (18) | C21C—C20C—H20B | 119.5 |
| C8B—N1B—C1B | 113.48 (18) | C22C—C21C—C20C | 121.7 (2) |
| C8B—N1B—B1B | 122.40 (18) | C22C—C21C—H21B | 119.1 |
| C1B—N1B—B1B | 123.49 (18) | C20C—C21C—H21B | 119.1 |
| C8B—N2B—C9B | 116.97 (18) | C21C—C22C—C23C | 117.9 (2) |
| C9B—N3B—C16B | 112.23 (17) | C21C—C22C—H22B | 121.0 |
| C9B—N3B—B1B | 122.45 (18) | C23C—C22C—H22B | 121.0 |
| C16B—N3B—B1B | 123.70 (18) | C22C—C23C—C18C | 120.3 (2) |
| C16B—N4B—C17B | 116.94 (18) | C22C—C23C—C24C | 132.4 (2) |
| C17B—N5B—C24B | 112.65 (18) | C18C—C23C—C24C | 107.14 (19) |
| C17B—N5B—B1B | 123.72 (18) | N6C—C24C—N5C | 122.1 (2) |
| C24B—N5B—B1B | 122.88 (18) | N6C—C24C—C23C | 130.92 (19) |
| C1B—N6B—C24B | 116.74 (18) | N5C—C24C—C23C | 105.76 (19) |
| N6B—C1B—N1B | 122.37 (19) | C25C—O1C—B1C | 125.3 (3) |
| N6B—C1B—C2B | 130.8 (2) | O1C—C25C—C26C | 116.1 (4) |
| N1B—C1B—C2B | 105.49 (18) | O1C—C25C—H25G | 108.3 |
| C3B—C2B—C7B | 120.3 (2) | C26C—C25C—H25G | 108.3 |
| C3B—C2B—C1B | 132.6 (2) | O1C—C25C—H25H | 108.3 |
| C7B—C2B—C1B | 107.05 (18) | C26C—C25C—H25H | 108.3 |
| C4B—C3B—C2B | 118.1 (2) | H25G—C25C—H25H | 107.4 |
| C4B—C3B—H3BA | 121.0 | C25C—C26C—C27C | 114.4 (5) |
| C2B—C3B—H3BA | 121.0 | C25C—C26C—H26G | 108.7 |
| C3B—C4B—C5B | 121.2 (2) | C27C—C26C—H26G | 108.7 |
| C3B—C4B—H4BA | 119.4 | C25C—C26C—H26H | 108.7 |
| C5B—C4B—H4BA | 119.4 | C27C—C26C—H26H | 108.7 |
| C6B—C5B—C4B | 121.5 (2) | H26G—C26C—H26H | 107.6 |
| C6B—C5B—H5BA | 119.3 | C26C—C27C—C28C | 113.4 (4) |
| C4B—C5B—H5BA | 119.3 | C26C—C27C—H27G | 108.9 |
| C5B—C6B—C7B | 118.0 (2) | C28C—C27C—H27G | 108.9 |
| C5B—C6B—H6BA | 121.0 | C26C—C27C—H27H | 108.9 |
| C7B—C6B—H6BA | 121.0 | C28C—C27C—H27H | 108.9 |
| C6B—C7B—C2B | 120.8 (2) | H27G—C27C—H27H | 107.7 |
| C6B—C7B—C8B | 131.7 (2) | C29C—C28C—C27C | 117.0 (6) |
| C2B—C7B—C8B | 107.41 (18) | C29C—C28C—H28G | 108.0 |
| N2B—C8B—N1B | 122.66 (19) | C27C—C28C—H28G | 108.0 |
| N2B—C8B—C7B | 130.29 (19) | C29C—C28C—H28H | 108.0 |
| N1B—C8B—C7B | 105.32 (18) | C27C—C28C—H28H | 108.0 |
| N2B—C9B—N3B | 122.60 (19) | H28G—C28C—H28H | 107.3 |
| N2B—C9B—C10B | 129.37 (19) | C28C—C29C—C30C | 113.8 (5) |
| N3B—C9B—C10B | 105.95 (18) | C28C—C29C—H29G | 108.8 |
| C11B—C10B—C15B | 120.7 (2) | C30C—C29C—H29G | 108.8 |
| C11B—C10B—C9B | 131.6 (2) | C28C—C29C—H29H | 108.8 |
| C15B—C10B—C9B | 107.33 (18) | C30C—C29C—H29H | 108.8 |
| C12B—C11B—C10B | 117.7 (2) | H29G—C29C—H29H | 107.7 |
| C12B—C11B—H11C | 121.2 | C31C—C30C—C29C | 115.7 (5) |
| C10B—C11B—H11C | 121.2 | C31C—C30C—H30G | 108.4 |
| C11B—C12B—C13B | 121.6 (2) | C29C—C30C—H30G | 108.4 |
| C11B—C12B—H12C | 119.2 | C31C—C30C—H30H | 108.4 |
| C13B—C12B—H12C | 119.2 | C29C—C30C—H30H | 108.4 |
| C14B—C13B—C12B | 121.1 (2) | H30G—C30C—H30H | 107.4 |
| C14B—C13B—H13C | 119.5 | C30C—C31C—C32C | 113.5 (8) |
| C12B—C13B—H13C | 119.5 | C30C—C31C—H31G | 108.9 |
| C13B—C14B—C15B | 118.2 (2) | C32C—C31C—H31G | 108.9 |
| C13B—C14B—H14C | 120.9 | C30C—C31C—H31H | 108.9 |
| C15B—C14B—H14C | 120.9 | C32C—C31C—H31H | 108.9 |
| C14B—C15B—C10B | 120.6 (2) | H31G—C31C—H31H | 107.7 |
| C14B—C15B—C16B | 131.9 (2) | C31C—C32C—H32G | 109.5 |
| C10B—C15B—C16B | 107.10 (19) | C31C—C32C—H32H | 109.5 |
| N4B—C16B—N3B | 122.59 (19) | H32G—C32C—H32H | 109.5 |
| N4B—C16B—C15B | 129.4 (2) | C31C—C32C—H32I | 109.5 |
| N3B—C16B—C15B | 106.27 (19) | H32G—C32C—H32I | 109.5 |
| N4B—C17B—N5B | 122.3 (2) | H32H—C32C—H32I | 109.5 |
| N4B—C17B—C18B | 130.0 (2) | C25E—O1E—B1C | 128.0 (3) |
| N5B—C17B—C18B | 106.08 (18) | O1E—C25E—C26E | 116.4 (4) |
| C19B—C18B—C23B | 121.0 (2) | O1E—C25E—H25J | 108.2 |
| C19B—C18B—C17B | 131.7 (2) | C26E—C25E—H25J | 108.2 |
| C23B—C18B—C17B | 107.16 (19) | O1E—C25E—H25K | 108.2 |
| C20B—C19B—C18B | 117.7 (2) | C26E—C25E—H25K | 108.2 |
| C20B—C19B—H19C | 121.2 | H25J—C25E—H25K | 107.3 |
| C18B—C19B—H19C | 121.2 | C25E—C26E—C27E | 113.0 (5) |
| C19B—C20B—C21B | 121.1 (2) | C25E—C26E—H26J | 109.0 |
| C19B—C20B—H20C | 119.4 | C27E—C26E—H26J | 109.0 |
| C21B—C20B—H20C | 119.4 | C25E—C26E—H26K | 109.0 |
| C22B—C21B—C20B | 122.1 (2) | C27E—C26E—H26K | 109.0 |
| C22B—C21B—H21C | 119.0 | H26J—C26E—H26K | 107.8 |
| C20B—C21B—H21C | 119.0 | C26E—C27E—C28E | 112.6 (5) |
| C21B—C22B—C23B | 117.7 (2) | C26E—C27E—H27J | 109.1 |
| C21B—C22B—H22C | 121.2 | C28E—C27E—H27J | 109.1 |
| C23B—C22B—H22C | 121.2 | C26E—C27E—H27K | 109.1 |
| C22B—C23B—C18B | 120.3 (2) | C28E—C27E—H27K | 109.1 |
| C22B—C23B—C24B | 132.7 (2) | H27J—C27E—H27K | 107.8 |
| C18B—C23B—C24B | 106.97 (19) | C27E—C28E—C29E | 115.5 (7) |
| N6B—C24B—N5B | 122.46 (19) | C27E—C28E—H28J | 108.4 |
| N6B—C24B—C23B | 130.1 (2) | C29E—C28E—H28J | 108.4 |
| N5B—C24B—C23B | 105.75 (18) | C27E—C28E—H28K | 108.4 |
| B1B—O1B—C25B | 119.09 (18) | C29E—C28E—H28K | 108.4 |
| B1B—O1B—C25D | 119.09 (18) | H28J—C28E—H28K | 107.5 |
| O1B—C25B—C26B | 110.4 (2) | C30E—C29E—C28E | 113.3 (7) |
| O1B—C25B—H25C | 109.6 | C30E—C29E—H29J | 108.9 |
| C26B—C25B—H25C | 109.6 | C28E—C29E—H29J | 108.9 |
| O1B—C25B—H25D | 109.6 | C30E—C29E—H29K | 108.9 |
| C26B—C25B—H25D | 109.6 | C28E—C29E—H29K | 108.9 |
| H25C—C25B—H25D | 108.1 | H29J—C29E—H29K | 107.7 |
| C27B—C26B—C25B | 111.5 (3) | C29E—C30E—C31E | 111.6 (6) |
| C27B—C26B—H26C | 109.3 | C29E—C30E—H30J | 109.3 |
| C25B—C26B—H26C | 109.3 | C31E—C30E—H30J | 109.3 |
| C27B—C26B—H26D | 109.3 | C29E—C30E—H30K | 109.3 |
| C25B—C26B—H26D | 109.3 | C31E—C30E—H30K | 109.3 |
| H26C—C26B—H26D | 108.0 | H30J—C30E—H30K | 108.0 |
| C26B—C27B—C28B | 116.8 (4) | C30E—C31E—C32E | 105.4 (8) |
| C26B—C27B—H27C | 108.1 | C30E—C31E—H31J | 110.7 |
| C28B—C27B—H27C | 108.1 | C32E—C31E—H31J | 110.7 |
| C26B—C27B—H27D | 108.1 | C30E—C31E—H31K | 110.7 |
| C28B—C27B—H27D | 108.1 | C32E—C31E—H31K | 110.7 |
| H27C—C27B—H27D | 107.3 | H31J—C31E—H31K | 108.8 |
| C29B—C28B—C27B | 117.2 (5) | C31E—C32E—H32J | 109.5 |
| C29B—C28B—H28C | 108.0 | C31E—C32E—H32K | 109.5 |
| C27B—C28B—H28C | 108.0 | H32J—C32E—H32K | 109.5 |
| C29B—C28B—H28D | 108.0 | C31E—C32E—H32L | 109.5 |
| C27B—C28B—H28D | 108.0 | H32J—C32E—H32L | 109.5 |
| H28C—C28B—H28D | 107.2 | H32K—C32E—H32L | 109.5 |
| C28B—C29B—C30B | 114.0 (5) | O1E—B1C—N5C | 113.6 (2) |
| C28B—C29B—H29C | 108.8 | O1C—B1C—N5C | 113.6 (2) |
| C30B—C29B—H29C | 108.8 | O1E—B1C—N1C | 114.8 (2) |
| C28B—C29B—H29D | 108.8 | O1C—B1C—N1C | 114.8 (2) |
| C30B—C29B—H29D | 108.8 | N5C—B1C—N1C | 103.66 (17) |
| H29C—C29B—H29D | 107.6 | O1E—B1C—N3C | 117.28 (18) |
| C31B—C30B—C29B | 107.0 (4) | O1C—B1C—N3C | 117.28 (18) |
| C31B—C30B—H30C | 110.3 | N5C—B1C—N3C | 102.80 (18) |
| C29B—C30B—H30C | 110.3 | N1C—B1C—N3C | 102.97 (19) |
| C31B—C30B—H30D | 110.3 | H1WB—O1W—H1WA | 98.6 |
| C29B—C30B—H30D | 110.3 | ||
| C24A—N6A—C1A—N1A | −9.4 (3) | C18B—C19B—C20B—C21B | 2.1 (4) |
| C24A—N6A—C1A—C2A | 151.6 (2) | C19B—C20B—C21B—C22B | 0.1 (4) |
| C8A—N1A—C1A—N6A | 153.4 (2) | C20B—C21B—C22B—C23B | −1.8 (4) |
| B1A—N1A—C1A—N6A | −13.3 (3) | C21B—C22B—C23B—C18B | 1.1 (3) |
| C8A—N1A—C1A—C2A | −11.3 (2) | C21B—C22B—C23B—C24B | 179.1 (2) |
| B1A—N1A—C1A—C2A | −178.0 (2) | C19B—C18B—C23B—C22B | 1.1 (3) |
| N6A—C1A—C2A—C3A | 15.6 (4) | C17B—C18B—C23B—C22B | 178.4 (2) |
| N1A—C1A—C2A—C3A | 179.0 (2) | C19B—C18B—C23B—C24B | −177.3 (2) |
| N6A—C1A—C2A—C7A | −156.3 (2) | C17B—C18B—C23B—C24B | 0.0 (2) |
| N1A—C1A—C2A—C7A | 7.1 (2) | C1B—N6B—C24B—N5B | 7.5 (3) |
| C7A—C2A—C3A—C4A | 0.3 (3) | C1B—N6B—C24B—C23B | −155.6 (2) |
| C1A—C2A—C3A—C4A | −170.6 (2) | C17B—N5B—C24B—N6B | −154.7 (2) |
| C2A—C3A—C4A—C5A | 0.3 (4) | B1B—N5B—C24B—N6B | 15.7 (3) |
| C3A—C4A—C5A—C6A | −0.4 (4) | C17B—N5B—C24B—C23B | 12.0 (2) |
| C4A—C5A—C6A—C7A | 0.0 (4) | B1B—N5B—C24B—C23B | −177.59 (18) |
| C5A—C6A—C7A—C2A | 0.6 (3) | C22B—C23B—C24B—N6B | −19.8 (4) |
| C5A—C6A—C7A—C8A | 171.7 (2) | C18B—C23B—C24B—N6B | 158.4 (2) |
| C3A—C2A—C7A—C6A | −0.8 (3) | C22B—C23B—C24B—N5B | 174.9 (2) |
| C1A—C2A—C7A—C6A | 172.2 (2) | C18B—C23B—C24B—N5B | −6.9 (2) |
| C3A—C2A—C7A—C8A | −173.9 (2) | B1B—O1B—C25B—C26B | 105.0 (2) |
| C1A—C2A—C7A—C8A | −0.9 (2) | O1B—C25B—C26B—C27B | 65.9 (3) |
| C9A—N2A—C8A—N1A | 8.4 (3) | C25B—C26B—C27B—C28B | −171.3 (4) |
| C9A—N2A—C8A—C7A | −152.9 (2) | C26B—C27B—C28B—C29B | 59.0 (7) |
| C1A—N1A—C8A—N2A | −154.2 (2) | C27B—C28B—C29B—C30B | 71.1 (7) |
| B1A—N1A—C8A—N2A | 12.5 (3) | C28B—C29B—C30B—C31B | −170.4 (5) |
| C1A—N1A—C8A—C7A | 10.8 (2) | C29B—C30B—C31B—C32B | −69.2 (6) |
| B1A—N1A—C8A—C7A | 177.5 (2) | B1B—O1B—C25D—C26D | 105.0 (2) |
| C6A—C7A—C8A—N2A | −13.9 (4) | O1B—C25D—C26D—C27D | 38.3 (9) |
| C2A—C7A—C8A—N2A | 158.0 (2) | C25D—C26D—C27D—C28D | 179.8 (10) |
| C6A—C7A—C8A—N1A | −177.6 (2) | C26D—C27D—C28D—C29D | 171.4 (12) |
| C2A—C7A—C8A—N1A | −5.7 (2) | C27D—C28D—C29D—C30D | −62.7 (14) |
| C8A—N2A—C9A—N3A | −7.7 (3) | C28D—C29D—C30D—C31D | −139.0 (9) |
| C8A—N2A—C9A—C10A | 153.0 (2) | C29D—C30D—C31D—C32D | 87.0 (15) |
| C16A—N3A—C9A—N2A | 153.0 (2) | C25B—O1B—B1B—N1B | −165.08 (18) |
| B1A—N3A—C9A—N2A | −13.8 (3) | C25D—O1B—B1B—N1B | −165.08 (18) |
| C16A—N3A—C9A—C10A | −11.5 (2) | C25B—O1B—B1B—N5B | 77.6 (3) |
| B1A—N3A—C9A—C10A | −178.27 (19) | C25D—O1B—B1B—N5B | 77.6 (3) |
| N2A—C9A—C10A—C11A | 17.6 (4) | C25B—O1B—B1B—N3B | −46.1 (3) |
| N3A—C9A—C10A—C11A | −179.3 (2) | C25D—O1B—B1B—N3B | −46.1 (3) |
| N2A—C9A—C10A—C15A | −156.2 (2) | C8B—N1B—B1B—O1B | 95.1 (2) |
| N3A—C9A—C10A—C15A | 6.9 (2) | C1B—N1B—B1B—O1B | −94.6 (2) |
| C15A—C10A—C11A—C12A | 0.3 (3) | C8B—N1B—B1B—N5B | −138.82 (19) |
| C9A—C10A—C11A—C12A | −172.8 (2) | C1B—N1B—B1B—N5B | 31.5 (2) |
| C10A—C11A—C12A—C13A | 0.6 (4) | C8B—N1B—B1B—N3B | −32.3 (3) |
| C11A—C12A—C13A—C14A | −0.6 (4) | C1B—N1B—B1B—N3B | 137.99 (19) |
| C12A—C13A—C14A—C15A | −0.4 (4) | C17B—N5B—B1B—O1B | −101.0 (2) |
| C13A—C14A—C15A—C10A | 1.3 (3) | C24B—N5B—B1B—O1B | 89.7 (3) |
| C13A—C14A—C15A—C16A | 173.2 (2) | C17B—N5B—B1B—N1B | 137.43 (19) |
| C11A—C10A—C15A—C14A | −1.3 (3) | C24B—N5B—B1B—N1B | −32.0 (2) |
| C9A—C10A—C15A—C14A | 173.4 (2) | C17B—N5B—B1B—N3B | 30.3 (3) |
| C11A—C10A—C15A—C16A | −175.02 (19) | C24B—N5B—B1B—N3B | −139.10 (19) |
| C9A—C10A—C15A—C16A | −0.3 (2) | C9B—N3B—B1B—O1B | −92.4 (3) |
| C17A—N4A—C16A—N3A | 9.2 (3) | C16B—N3B—B1B—O1B | 103.3 (2) |
| C17A—N4A—C16A—C15A | −152.6 (2) | C9B—N3B—B1B—N1B | 30.3 (3) |
| C9A—N3A—C16A—N4A | −154.1 (2) | C16B—N3B—B1B—N1B | −134.0 (2) |
| B1A—N3A—C16A—N4A | 12.5 (3) | C9B—N3B—B1B—N5B | 136.8 (2) |
| C9A—N3A—C16A—C15A | 11.3 (2) | C16B—N3B—B1B—N5B | −27.6 (3) |
| B1A—N3A—C16A—C15A | 177.93 (19) | C24C—N6C—C1C—N1C | −6.6 (3) |
| C14A—C15A—C16A—N4A | −14.9 (4) | C24C—N6C—C1C—C2C | 156.4 (2) |
| C10A—C15A—C16A—N4A | 157.8 (2) | C8C—N1C—C1C—N6C | 153.4 (2) |
| C14A—C15A—C16A—N3A | −179.0 (2) | B1C—N1C—C1C—N6C | −15.0 (3) |
| C10A—C15A—C16A—N3A | −6.3 (2) | C8C—N1C—C1C—C2C | −13.1 (2) |
| C16A—N4A—C17A—N5A | −8.4 (3) | B1C—N1C—C1C—C2C | 178.50 (19) |
| C16A—N4A—C17A—C18A | 154.0 (2) | N6C—C1C—C2C—C3C | 18.6 (4) |
| C24A—N5A—C17A—N4A | 154.4 (2) | N1C—C1C—C2C—C3C | −176.4 (2) |
| B1A—N5A—C17A—N4A | −14.2 (3) | N6C—C1C—C2C—C7C | −157.4 (2) |
| C24A—N5A—C17A—C18A | −11.6 (2) | N1C—C1C—C2C—C7C | 7.7 (2) |
| B1A—N5A—C17A—C18A | 179.84 (19) | C7C—C2C—C3C—C4C | −1.4 (3) |
| N4A—C17A—C18A—C19A | 16.3 (4) | C1C—C2C—C3C—C4C | −176.9 (2) |
| N5A—C17A—C18A—C19A | −179.2 (2) | C2C—C3C—C4C—C5C | 1.7 (4) |
| N4A—C17A—C18A—C23A | −157.5 (2) | C3C—C4C—C5C—C6C | −0.5 (5) |
| N5A—C17A—C18A—C23A | 7.0 (2) | C4C—C5C—C6C—C7C | −1.1 (4) |
| C23A—C18A—C19A—C20A | 0.0 (3) | C5C—C6C—C7C—C2C | 1.4 (4) |
| C17A—C18A—C19A—C20A | −173.1 (2) | C5C—C6C—C7C—C8C | 177.0 (3) |
| C18A—C19A—C20A—C21A | 0.4 (3) | C3C—C2C—C7C—C6C | −0.1 (3) |
| C19A—C20A—C21A—C22A | 0.0 (4) | C1C—C2C—C7C—C6C | 176.3 (2) |
| C20A—C21A—C22A—C23A | −0.9 (3) | C3C—C2C—C7C—C8C | −176.7 (2) |
| C21A—C22A—C23A—C18A | 1.3 (3) | C1C—C2C—C7C—C8C | −0.3 (2) |
| C21A—C22A—C23A—C24A | 174.0 (2) | C9C—N2C—C8C—N1C | 8.2 (3) |
| C19A—C18A—C23A—C22A | −0.9 (3) | C9C—N2C—C8C—C7C | −155.2 (2) |
| C17A—C18A—C23A—C22A | 173.7 (2) | C1C—N1C—C8C—N2C | −154.0 (2) |
| C19A—C18A—C23A—C24A | −175.2 (2) | B1C—N1C—C8C—N2C | 14.3 (3) |
| C17A—C18A—C23A—C24A | −0.6 (2) | C1C—N1C—C8C—C7C | 12.9 (2) |
| C1A—N6A—C24A—N5A | 9.4 (3) | B1C—N1C—C8C—C7C | −178.77 (19) |
| C1A—N6A—C24A—C23A | −154.0 (2) | C6C—C7C—C8C—N2C | −17.8 (4) |
| C17A—N5A—C24A—N6A | −155.6 (2) | C2C—C7C—C8C—N2C | 158.3 (2) |
| B1A—N5A—C24A—N6A | 13.2 (3) | C6C—C7C—C8C—N1C | 176.7 (3) |
| C17A—N5A—C24A—C23A | 11.2 (2) | C2C—C7C—C8C—N1C | −7.3 (2) |
| B1A—N5A—C24A—C23A | 179.9 (2) | C8C—N2C—C9C—N3C | −8.8 (3) |
| C22A—C23A—C24A—N6A | −14.1 (4) | C8C—N2C—C9C—C10C | 157.1 (2) |
| C18A—C23A—C24A—N6A | 159.4 (2) | C16C—N3C—C9C—N2C | 157.42 (19) |
| C22A—C23A—C24A—N5A | −179.6 (2) | B1C—N3C—C9C—N2C | −13.0 (3) |
| C18A—C23A—C24A—N5A | −6.1 (2) | C16C—N3C—C9C—C10C | −11.6 (2) |
| B1A—O1A—C25A—C26A | 110.0 (3) | B1C—N3C—C9C—C10C | 177.97 (18) |
| O1A—C25A—C26A—C27A | 174.7 (2) | N2C—C9C—C10C—C11C | 16.3 (4) |
| C25A—C26A—C27A—C28A | −175.7 (3) | N3C—C9C—C10C—C11C | −176.0 (2) |
| C26A—C27A—C28A—C29A | 176.8 (3) | N2C—C9C—C10C—C15C | −162.0 (2) |
| C27A—C28A—C29A—C30A | −175.4 (3) | N3C—C9C—C10C—C15C | 5.7 (2) |
| C28A—C29A—C30A—C31A | 173.6 (3) | C15C—C10C—C11C—C12C | −3.6 (3) |
| C29A—C30A—C31A—C32A | −179.4 (2) | C9C—C10C—C11C—C12C | 178.3 (2) |
| C25A—O1A—B1A—N1A | −177.44 (19) | C10C—C11C—C12C—C13C | 2.4 (3) |
| C25A—O1A—B1A—N5A | 64.0 (3) | C11C—C12C—C13C—C14C | 1.1 (3) |
| C25A—O1A—B1A—N3A | −57.8 (3) | C12C—C13C—C14C—C15C | −3.2 (3) |
| C1A—N1A—B1A—O1A | −95.9 (3) | C13C—C14C—C15C—C10C | 2.0 (3) |
| C8A—N1A—B1A—O1A | 98.8 (2) | C13C—C14C—C15C—C16C | −179.9 (2) |
| C1A—N1A—B1A—N5A | 30.2 (3) | C11C—C10C—C15C—C14C | 1.5 (3) |
| C8A—N1A—B1A—N5A | −135.1 (2) | C9C—C10C—C15C—C14C | 180.00 (19) |
| C1A—N1A—B1A—N3A | 136.8 (2) | C11C—C10C—C15C—C16C | −177.09 (19) |
| C8A—N1A—B1A—N3A | −28.5 (3) | C9C—C10C—C15C—C16C | 1.4 (2) |
| C24A—N5A—B1A—O1A | 93.1 (2) | C17C—N4C—C16C—N3C | 9.0 (3) |
| C17A—N5A—B1A—O1A | −99.5 (3) | C17C—N4C—C16C—C15C | −156.6 (2) |
| C24A—N5A—B1A—N1A | −30.1 (3) | C9C—N3C—C16C—N4C | −156.07 (19) |
| C17A—N5A—B1A—N1A | 137.4 (2) | B1C—N3C—C16C—N4C | 14.4 (3) |
| C24A—N5A—B1A—N3A | −137.5 (2) | C9C—N3C—C16C—C15C | 12.6 (2) |
| C17A—N5A—B1A—N3A | 29.9 (3) | B1C—N3C—C16C—C15C | −176.95 (18) |
| C9A—N3A—B1A—O1A | −94.8 (2) | C14C—C15C—C16C—N4C | −19.1 (4) |
| C16A—N3A—B1A—O1A | 99.9 (2) | C10C—C15C—C16C—N4C | 159.2 (2) |
| C9A—N3A—B1A—N1A | 29.1 (3) | C14C—C15C—C16C—N3C | 173.5 (2) |
| C16A—N3A—B1A—N1A | −136.2 (2) | C10C—C15C—C16C—N3C | −8.1 (2) |
| C9A—N3A—B1A—N5A | 136.29 (19) | C16C—N4C—C17C—N5C | −8.3 (3) |
| C16A—N3A—B1A—N5A | −29.0 (3) | C16C—N4C—C17C—C18C | 155.5 (2) |
| C24B—N6B—C1B—N1B | −8.2 (3) | C24C—N5C—C17C—N4C | 154.6 (2) |
| C24B—N6B—C1B—C2B | 156.6 (2) | B1C—N5C—C17C—N4C | −15.9 (3) |
| C8B—N1B—C1B—N6B | 156.63 (19) | C24C—N5C—C17C—C18C | −12.6 (2) |
| B1B—N1B—C1B—N6B | −14.5 (3) | B1C—N5C—C17C—C18C | 176.9 (2) |
| C8B—N1B—C1B—C2B | −11.5 (2) | N4C—C17C—C18C—C19C | 19.7 (4) |
| B1B—N1B—C1B—C2B | 177.39 (18) | N5C—C17C—C18C—C19C | −174.4 (2) |
| N6B—C1B—C2B—C3B | 17.5 (4) | N4C—C17C—C18C—C23C | −157.6 (2) |
| N1B—C1B—C2B—C3B | −175.8 (2) | N5C—C17C—C18C—C23C | 8.3 (2) |
| N6B—C1B—C2B—C7B | −160.0 (2) | C23C—C18C—C19C—C20C | 0.3 (4) |
| N1B—C1B—C2B—C7B | 6.7 (2) | C17C—C18C—C19C—C20C | −176.8 (2) |
| C7B—C2B—C3B—C4B | −1.4 (3) | C18C—C19C—C20C—C21C | 1.9 (4) |
| C1B—C2B—C3B—C4B | −178.6 (2) | C19C—C20C—C21C—C22C | −2.0 (4) |
| C2B—C3B—C4B—C5B | 1.2 (3) | C20C—C21C—C22C—C23C | −0.3 (4) |
| C3B—C4B—C5B—C6B | 0.7 (3) | C21C—C22C—C23C—C18C | 2.5 (3) |
| C4B—C5B—C6B—C7B | −2.3 (3) | C21C—C22C—C23C—C24C | 178.4 (2) |
| C5B—C6B—C7B—C2B | 2.1 (3) | C19C—C18C—C23C—C22C | −2.5 (3) |
| C5B—C6B—C7B—C8B | 179.3 (2) | C17C—C18C—C23C—C22C | 175.2 (2) |
| C3B—C2B—C7B—C6B | −0.2 (3) | C19C—C18C—C23C—C24C | −179.4 (2) |
| C1B—C2B—C7B—C6B | 177.64 (19) | C17C—C18C—C23C—C24C | −1.6 (2) |
| C3B—C2B—C7B—C8B | −178.10 (19) | C1C—N6C—C24C—N5C | 7.4 (3) |
| C1B—C2B—C7B—C8B | −0.2 (2) | C1C—N6C—C24C—C23C | −157.9 (2) |
| C9B—N2B—C8B—N1B | 8.1 (3) | C17C—N5C—C24C—N6C | −156.9 (2) |
| C9B—N2B—C8B—C7B | −154.6 (2) | B1C—N5C—C24C—N6C | 13.5 (3) |
| C1B—N1B—C8B—N2B | −155.1 (2) | C17C—N5C—C24C—C23C | 11.6 (2) |
| B1B—N1B—C8B—N2B | 16.1 (3) | B1C—N5C—C24C—C23C | −178.02 (19) |
| C1B—N1B—C8B—C7B | 11.3 (2) | C22C—C23C—C24C—N6C | −14.9 (4) |
| B1B—N1B—C8B—C7B | −177.44 (18) | C18C—C23C—C24C—N6C | 161.4 (2) |
| C6B—C7B—C8B—N2B | −18.9 (4) | C22C—C23C—C24C—N5C | 178.1 (2) |
| C2B—C7B—C8B—N2B | 158.6 (2) | C18C—C23C—C24C—N5C | −5.6 (2) |
| C6B—C7B—C8B—N1B | 176.1 (2) | B1C—O1C—C25C—C26C | 174.3 (4) |
| C2B—C7B—C8B—N1B | −6.4 (2) | O1C—C25C—C26C—C27C | −74.6 (6) |
| C8B—N2B—C9B—N3B | −10.1 (3) | C25C—C26C—C27C—C28C | −164.4 (7) |
| C8B—N2B—C9B—C10B | 151.0 (2) | C26C—C27C—C28C—C29C | 179.9 (8) |
| C16B—N3B—C9B—N2B | 154.0 (2) | C27C—C28C—C29C—C30C | −174.5 (8) |
| B1B—N3B—C9B—N2B | −11.9 (3) | C28C—C29C—C30C—C31C | −169.9 (8) |
| C16B—N3B—C9B—C10B | −10.9 (2) | C29C—C30C—C31C—C32C | −63.5 (10) |
| B1B—N3B—C9B—C10B | −176.88 (19) | B1C—O1E—C25E—C26E | −166.9 (4) |
| N2B—C9B—C10B—C11B | 16.2 (4) | O1E—C25E—C26E—C27E | −171.1 (5) |
| N3B—C9B—C10B—C11B | 179.7 (2) | C25E—C26E—C27E—C28E | −172.2 (7) |
| N2B—C9B—C10B—C15B | −156.8 (2) | C26E—C27E—C28E—C29E | −172.9 (7) |
| N3B—C9B—C10B—C15B | 6.8 (2) | C27E—C28E—C29E—C30E | −67.4 (11) |
| C15B—C10B—C11B—C12B | 0.2 (3) | C28E—C29E—C30E—C31E | −172.0 (8) |
| C9B—C10B—C11B—C12B | −171.9 (2) | C29E—C30E—C31E—C32E | 175.0 (8) |
| C10B—C11B—C12B—C13B | 0.1 (4) | C25E—O1E—B1C—N5C | 162.1 (4) |
| C11B—C12B—C13B—C14B | 0.1 (4) | C25E—O1E—B1C—N1C | −78.8 (4) |
| C12B—C13B—C14B—C15B | −0.7 (4) | C25E—O1E—B1C—N3C | 42.3 (5) |
| C13B—C14B—C15B—C10B | 1.1 (3) | C25C—O1C—B1C—N5C | 68.8 (4) |
| C13B—C14B—C15B—C16B | 172.9 (2) | C25C—O1C—B1C—N1C | −172.2 (3) |
| C11B—C10B—C15B—C14B | −0.9 (3) | C25C—O1C—B1C—N3C | −51.0 (4) |
| C9B—C10B—C15B—C14B | 173.0 (2) | C24C—N5C—B1C—O1E | 95.8 (3) |
| C11B—C10B—C15B—C16B | −174.5 (2) | C17C—N5C—B1C—O1E | −94.7 (2) |
| C9B—C10B—C15B—C16B | −0.6 (2) | C24C—N5C—B1C—O1C | 95.8 (3) |
| C17B—N4B—C16B—N3B | 10.4 (3) | C17C—N5C—B1C—O1C | −94.7 (2) |
| C17B—N4B—C16B—C15B | −152.4 (2) | C24C—N5C—B1C—N1C | −29.5 (3) |
| C9B—N3B—C16B—N4B | −155.7 (2) | C17C—N5C—B1C—N1C | 140.0 (2) |
| B1B—N3B—C16B—N4B | 10.1 (3) | C24C—N5C—B1C—N3C | −136.5 (2) |
| C9B—N3B—C16B—C15B | 10.6 (2) | C17C—N5C—B1C—N3C | 33.0 (3) |
| B1B—N3B—C16B—C15B | 176.33 (19) | C8C—N1C—B1C—O1E | 98.4 (3) |
| C14B—C15B—C16B—N4B | −13.4 (4) | C1C—N1C—B1C—O1E | −94.4 (3) |
| C10B—C15B—C16B—N4B | 159.3 (2) | C8C—N1C—B1C—O1C | 98.4 (3) |
| C14B—C15B—C16B—N3B | −178.4 (2) | C1C—N1C—B1C—O1C | −94.4 (3) |
| C10B—C15B—C16B—N3B | −5.7 (2) | C8C—N1C—B1C—N5C | −137.1 (2) |
| C16B—N4B—C17B—N5B | −7.8 (3) | C1C—N1C—B1C—N5C | 30.0 (3) |
| C16B—N4B—C17B—C18B | 155.4 (2) | C8C—N1C—B1C—N3C | −30.3 (3) |
| C24B—N5B—C17B—N4B | 154.7 (2) | C1C—N1C—B1C—N3C | 136.90 (19) |
| B1B—N5B—C17B—N4B | −15.6 (3) | C16C—N3C—B1C—O1E | 93.0 (3) |
| C24B—N5B—C17B—C18B | −12.0 (2) | C9C—N3C—B1C—O1E | −97.5 (3) |
| B1B—N5B—C17B—C18B | 177.66 (19) | C16C—N3C—B1C—O1C | 93.0 (3) |
| N4B—C17B—C18B—C19B | 18.6 (4) | C9C—N3C—B1C—O1C | −97.5 (3) |
| N5B—C17B—C18B—C19B | −176.1 (2) | C16C—N3C—B1C—N5C | −32.4 (3) |
| N4B—C17B—C18B—C23B | −158.4 (2) | C9C—N3C—B1C—N5C | 137.2 (2) |
| N5B—C17B—C18B—C23B | 6.9 (2) | C16C—N3C—B1C—N1C | −139.87 (19) |
| C23B—C18B—C19B—C20B | −2.6 (3) | C9C—N3C—B1C—N1C | 29.6 (3) |
| C17B—C18B—C19B—C20B | −179.3 (2) |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1W—H1WB···N6A | 0.84 | 2.16 | 3.005 (8) | 179 |
| O1W—H1WA···N4Bi | 0.84 | 2.20 | 3.043 (9) | 179 |
| Symmetry code: (i) −x+1, −y+1, −z+1. |
(Phenolato)(subphthalocyaninato)boron (d2335_a) top
Crystal data top
| C30H17BN6O | Z = 2 |
| Mr = 488.30 | F(000) = 504 |
| Triclinic, P1 | Dx = 1.431 Mg m−3 |
| a = 10.0268 (10) Å | Mo Kα radiation, λ = 0.71073 Å |
| b = 10.7263 (12) Å | Cell parameters from 6094 reflections |
| c = 11.8090 (13) Å | θ = 2.3–27.2° |
| α = 85.879 (4)° | µ = 0.09 mm−1 |
| β = 77.440 (3)° | T = 150 K |
| γ = 66.151 (3)° | Shard, pink |
| V = 1133.6 (2) Å3 | 0.28 × 0.15 × 0.09 mm |
Data collection top
| Bruker Kappa APEX-DUO CMOS PHOTON II diffractometer | 3795 reflections with I > 2σ(I) |
| Radiation source: sealed tube with Bruker Triumph monochromator | Rint = 0.052 |
| φ and ω scans | θmax = 27.5°, θmin = 1.8° |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −12→11 |
| Tmin = 0.687, Tmax = 0.746 | k = −13→13 |
| 26461 measured reflections | l = −15→15 |
| 5137 independent reflections |
Refinement top
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
| wR(F2) = 0.095 | w = 1/[σ2(Fo2) + (0.0462P)2 + 0.1591P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.03 | (Δ/σ)max < 0.001 |
| 5137 reflections | Δρmax = 0.22 e Å−3 |
| 343 parameters | Δρmin = −0.23 e Å−3 |
| 0 restraints |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.60836 (9) | 0.58360 (9) | 0.39809 (7) | 0.0225 (2) | |
| N1 | 0.82829 (12) | 0.20316 (11) | 0.37311 (9) | 0.0217 (2) | |
| N2 | 0.86304 (11) | 0.41087 (11) | 0.36391 (9) | 0.0200 (2) | |
| N3 | 0.99417 (12) | 0.54932 (11) | 0.28170 (10) | 0.0229 (2) | |
| N4 | 0.78717 (11) | 0.55805 (10) | 0.21103 (9) | 0.0194 (2) | |
| N5 | 0.66845 (11) | 0.50195 (10) | 0.08169 (9) | 0.0216 (2) | |
| N6 | 0.69756 (11) | 0.38657 (10) | 0.26052 (9) | 0.0200 (2) | |
| C1 | 0.89779 (14) | 0.27856 (13) | 0.39799 (11) | 0.0209 (3) | |
| C2 | 1.03999 (14) | 0.23562 (13) | 0.43385 (11) | 0.0219 (3) | |
| C3 | 1.13027 (15) | 0.11419 (14) | 0.47752 (11) | 0.0249 (3) | |
| H3A | 1.097207 | 0.042659 | 0.498462 | 0.030* | |
| C4 | 1.26953 (15) | 0.10072 (14) | 0.48954 (12) | 0.0282 (3) | |
| H4A | 1.332206 | 0.018810 | 0.519985 | 0.034* | |
| C5 | 1.32060 (15) | 0.20416 (15) | 0.45819 (12) | 0.0301 (3) | |
| H5A | 1.417158 | 0.191245 | 0.467242 | 0.036* | |
| C6 | 1.23264 (15) | 0.32495 (14) | 0.41420 (12) | 0.0279 (3) | |
| H6A | 1.267864 | 0.394918 | 0.392013 | 0.033* | |
| C7 | 1.09155 (14) | 0.34156 (13) | 0.40321 (11) | 0.0222 (3) | |
| C8 | 0.97963 (14) | 0.44909 (13) | 0.35198 (11) | 0.0213 (3) | |
| C9 | 0.90088 (14) | 0.59754 (13) | 0.20773 (11) | 0.0216 (3) | |
| C10 | 0.91289 (14) | 0.66902 (13) | 0.09880 (11) | 0.0221 (3) | |
| C11 | 1.00034 (14) | 0.74072 (13) | 0.05127 (12) | 0.0266 (3) | |
| H11A | 1.069321 | 0.748820 | 0.091051 | 0.032* | |
| C12 | 0.98350 (15) | 0.79963 (14) | −0.05555 (13) | 0.0295 (3) | |
| H12A | 1.038160 | 0.852913 | −0.087655 | 0.035* | |
| C13 | 0.88785 (15) | 0.78252 (14) | −0.11731 (12) | 0.0284 (3) | |
| H13A | 0.879883 | 0.823482 | −0.190946 | 0.034* | |
| C14 | 0.80442 (14) | 0.70726 (13) | −0.07371 (12) | 0.0250 (3) | |
| H14A | 0.742488 | 0.693035 | −0.117405 | 0.030* | |
| C15 | 0.81440 (14) | 0.65294 (13) | 0.03674 (11) | 0.0217 (3) | |
| C16 | 0.74174 (13) | 0.57282 (12) | 0.10831 (11) | 0.0204 (3) | |
| C17 | 0.65606 (13) | 0.40411 (13) | 0.15564 (11) | 0.0206 (3) | |
| C18 | 0.63636 (13) | 0.28129 (13) | 0.13500 (11) | 0.0206 (3) | |
| C19 | 0.59450 (14) | 0.24229 (14) | 0.04296 (12) | 0.0244 (3) | |
| H19A | 0.563656 | 0.303407 | −0.017647 | 0.029* | |
| C20 | 0.59931 (15) | 0.11185 (14) | 0.04268 (12) | 0.0273 (3) | |
| H20A | 0.568344 | 0.083898 | −0.017991 | 0.033* | |
| C21 | 0.64868 (15) | 0.02013 (14) | 0.12962 (12) | 0.0258 (3) | |
| H21A | 0.650520 | −0.068858 | 0.126791 | 0.031* | |
| C22 | 0.69491 (14) | 0.05581 (13) | 0.21967 (12) | 0.0230 (3) | |
| H22A | 0.731545 | −0.008265 | 0.276977 | 0.028* | |
| C23 | 0.68631 (13) | 0.18853 (13) | 0.22413 (11) | 0.0208 (3) | |
| C24 | 0.73460 (14) | 0.25611 (13) | 0.29959 (11) | 0.0202 (3) | |
| C25 | 0.48406 (14) | 0.66715 (13) | 0.35606 (11) | 0.0213 (3) | |
| C26 | 0.37130 (15) | 0.62436 (15) | 0.35710 (12) | 0.0287 (3) | |
| H26A | 0.378545 | 0.538020 | 0.387713 | 0.034* | |
| C27 | 0.24733 (16) | 0.70750 (17) | 0.31343 (13) | 0.0359 (4) | |
| H27A | 0.170203 | 0.677554 | 0.313346 | 0.043* | |
| C28 | 0.23567 (16) | 0.83366 (17) | 0.27007 (13) | 0.0373 (4) | |
| H28A | 0.150759 | 0.890544 | 0.240092 | 0.045* | |
| C29 | 0.34800 (16) | 0.87679 (15) | 0.27049 (13) | 0.0330 (3) | |
| H29A | 0.339533 | 0.963989 | 0.241377 | 0.040* | |
| C30 | 0.47267 (15) | 0.79420 (14) | 0.31288 (12) | 0.0256 (3) | |
| H30A | 0.549959 | 0.824095 | 0.312488 | 0.031* | |
| B1 | 0.72912 (16) | 0.49125 (15) | 0.31433 (13) | 0.0202 (3) |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0238 (5) | 0.0221 (5) | 0.0209 (5) | −0.0078 (4) | −0.0059 (4) | 0.0012 (4) |
| N1 | 0.0255 (6) | 0.0218 (6) | 0.0196 (6) | −0.0112 (5) | −0.0053 (5) | 0.0021 (4) |
| N2 | 0.0231 (5) | 0.0187 (6) | 0.0196 (6) | −0.0091 (4) | −0.0061 (4) | 0.0021 (4) |
| N3 | 0.0251 (6) | 0.0196 (6) | 0.0262 (6) | −0.0096 (5) | −0.0087 (5) | 0.0019 (5) |
| N4 | 0.0204 (5) | 0.0162 (5) | 0.0212 (6) | −0.0066 (4) | −0.0053 (4) | 0.0012 (4) |
| N5 | 0.0214 (5) | 0.0176 (6) | 0.0246 (6) | −0.0059 (4) | −0.0067 (4) | 0.0023 (5) |
| N6 | 0.0212 (5) | 0.0184 (5) | 0.0208 (6) | −0.0079 (4) | −0.0059 (4) | 0.0020 (4) |
| C1 | 0.0252 (6) | 0.0190 (6) | 0.0177 (7) | −0.0081 (5) | −0.0051 (5) | 0.0026 (5) |
| C2 | 0.0263 (7) | 0.0227 (7) | 0.0167 (7) | −0.0090 (5) | −0.0058 (5) | −0.0007 (5) |
| C3 | 0.0315 (7) | 0.0223 (7) | 0.0208 (7) | −0.0091 (6) | −0.0092 (6) | 0.0022 (5) |
| C4 | 0.0329 (7) | 0.0247 (7) | 0.0231 (7) | −0.0042 (6) | −0.0127 (6) | 0.0016 (6) |
| C5 | 0.0261 (7) | 0.0338 (8) | 0.0303 (8) | −0.0078 (6) | −0.0135 (6) | −0.0014 (6) |
| C6 | 0.0294 (7) | 0.0277 (8) | 0.0309 (8) | −0.0130 (6) | −0.0122 (6) | 0.0006 (6) |
| C7 | 0.0268 (7) | 0.0214 (7) | 0.0196 (7) | −0.0085 (5) | −0.0091 (5) | 0.0001 (5) |
| C8 | 0.0234 (6) | 0.0201 (7) | 0.0220 (7) | −0.0093 (5) | −0.0063 (5) | −0.0017 (5) |
| C9 | 0.0219 (6) | 0.0171 (6) | 0.0257 (7) | −0.0080 (5) | −0.0039 (5) | −0.0012 (5) |
| C10 | 0.0203 (6) | 0.0162 (6) | 0.0257 (7) | −0.0045 (5) | −0.0026 (5) | 0.0010 (5) |
| C11 | 0.0224 (6) | 0.0216 (7) | 0.0326 (8) | −0.0070 (5) | −0.0029 (6) | 0.0017 (6) |
| C12 | 0.0249 (7) | 0.0248 (7) | 0.0329 (8) | −0.0090 (6) | 0.0029 (6) | 0.0053 (6) |
| C13 | 0.0287 (7) | 0.0239 (7) | 0.0235 (7) | −0.0052 (6) | 0.0010 (6) | 0.0045 (6) |
| C14 | 0.0243 (7) | 0.0214 (7) | 0.0235 (7) | −0.0044 (5) | −0.0027 (5) | 0.0001 (5) |
| C15 | 0.0220 (6) | 0.0154 (6) | 0.0231 (7) | −0.0040 (5) | −0.0022 (5) | 0.0007 (5) |
| C16 | 0.0194 (6) | 0.0166 (6) | 0.0215 (7) | −0.0035 (5) | −0.0047 (5) | 0.0009 (5) |
| C17 | 0.0183 (6) | 0.0204 (7) | 0.0218 (7) | −0.0056 (5) | −0.0059 (5) | 0.0003 (5) |
| C18 | 0.0177 (6) | 0.0194 (7) | 0.0245 (7) | −0.0072 (5) | −0.0045 (5) | 0.0009 (5) |
| C19 | 0.0239 (7) | 0.0240 (7) | 0.0267 (7) | −0.0088 (6) | −0.0105 (6) | 0.0032 (6) |
| C20 | 0.0286 (7) | 0.0282 (7) | 0.0286 (8) | −0.0125 (6) | −0.0097 (6) | −0.0029 (6) |
| C21 | 0.0280 (7) | 0.0204 (7) | 0.0306 (8) | −0.0112 (6) | −0.0056 (6) | −0.0012 (6) |
| C22 | 0.0248 (6) | 0.0200 (7) | 0.0245 (7) | −0.0098 (5) | −0.0046 (5) | 0.0025 (5) |
| C23 | 0.0186 (6) | 0.0216 (7) | 0.0220 (7) | −0.0087 (5) | −0.0031 (5) | 0.0020 (5) |
| C24 | 0.0211 (6) | 0.0188 (6) | 0.0204 (7) | −0.0085 (5) | −0.0030 (5) | 0.0021 (5) |
| C25 | 0.0216 (6) | 0.0229 (7) | 0.0164 (6) | −0.0059 (5) | −0.0028 (5) | −0.0019 (5) |
| C26 | 0.0280 (7) | 0.0329 (8) | 0.0273 (8) | −0.0157 (6) | −0.0026 (6) | −0.0002 (6) |
| C27 | 0.0254 (7) | 0.0519 (10) | 0.0325 (9) | −0.0170 (7) | −0.0052 (6) | −0.0053 (7) |
| C28 | 0.0279 (7) | 0.0438 (10) | 0.0307 (8) | −0.0017 (7) | −0.0101 (6) | −0.0044 (7) |
| C29 | 0.0380 (8) | 0.0249 (8) | 0.0287 (8) | −0.0040 (6) | −0.0086 (6) | −0.0005 (6) |
| C30 | 0.0284 (7) | 0.0225 (7) | 0.0248 (7) | −0.0087 (6) | −0.0057 (6) | −0.0015 (6) |
| B1 | 0.0233 (7) | 0.0177 (7) | 0.0213 (8) | −0.0092 (6) | −0.0068 (6) | 0.0025 (6) |
Geometric parameters (Å, º) top
| O1—C25 | 1.3801 (15) | C11—C12 | 1.382 (2) |
| O1—B1 | 1.4407 (17) | C11—H11A | 0.9500 |
| N1—C1 | 1.3435 (17) | C12—C13 | 1.397 (2) |
| N1—C24 | 1.3459 (16) | C12—H12A | 0.9500 |
| N2—C8 | 1.3646 (16) | C13—C14 | 1.3840 (19) |
| N2—C1 | 1.3699 (16) | C13—H13A | 0.9500 |
| N2—B1 | 1.4907 (17) | C14—C15 | 1.3968 (18) |
| N3—C9 | 1.3434 (16) | C14—H14A | 0.9500 |
| N3—C8 | 1.3460 (17) | C15—C16 | 1.4553 (18) |
| N4—C9 | 1.3601 (16) | C17—C18 | 1.4531 (18) |
| N4—C16 | 1.3632 (16) | C18—C19 | 1.3922 (18) |
| N4—B1 | 1.4977 (18) | C18—C23 | 1.4229 (18) |
| N5—C16 | 1.3428 (16) | C19—C20 | 1.3806 (19) |
| N5—C17 | 1.3438 (16) | C19—H19A | 0.9500 |
| N6—C17 | 1.3673 (16) | C20—C21 | 1.3961 (19) |
| N6—C24 | 1.3677 (16) | C20—H20A | 0.9500 |
| N6—B1 | 1.4974 (18) | C21—C22 | 1.3815 (19) |
| C1—C2 | 1.4587 (18) | C21—H21A | 0.9500 |
| C2—C3 | 1.3910 (18) | C22—C23 | 1.3952 (18) |
| C2—C7 | 1.4227 (18) | C22—H22A | 0.9500 |
| C3—C4 | 1.3824 (19) | C23—C24 | 1.4553 (18) |
| C3—H3A | 0.9500 | C25—C26 | 1.3791 (19) |
| C4—C5 | 1.396 (2) | C25—C30 | 1.3892 (19) |
| C4—H4A | 0.9500 | C26—C27 | 1.387 (2) |
| C5—C6 | 1.3802 (19) | C26—H26A | 0.9500 |
| C5—H5A | 0.9500 | C27—C28 | 1.380 (2) |
| C6—C7 | 1.3866 (19) | C27—H27A | 0.9500 |
| C6—H6A | 0.9500 | C28—C29 | 1.381 (2) |
| C7—C8 | 1.4504 (18) | C28—H28A | 0.9500 |
| C9—C10 | 1.4569 (18) | C29—C30 | 1.3824 (19) |
| C10—C11 | 1.3945 (18) | C29—H29A | 0.9500 |
| C10—C15 | 1.4187 (19) | C30—H30A | 0.9500 |
| C25—O1—B1 | 115.60 (10) | C14—C15—C10 | 120.64 (12) |
| C1—N1—C24 | 117.24 (11) | C14—C15—C16 | 132.10 (12) |
| C8—N2—C1 | 112.86 (10) | C10—C15—C16 | 107.24 (11) |
| C8—N2—B1 | 122.15 (11) | N5—C16—N4 | 122.23 (11) |
| C1—N2—B1 | 123.00 (10) | N5—C16—C15 | 131.32 (12) |
| C9—N3—C8 | 116.66 (11) | N4—C16—C15 | 105.34 (11) |
| C9—N4—C16 | 113.67 (11) | N5—C17—N6 | 122.99 (11) |
| C9—N4—B1 | 122.62 (11) | N5—C17—C18 | 129.76 (12) |
| C16—N4—B1 | 123.41 (11) | N6—C17—C18 | 105.53 (11) |
| C16—N5—C17 | 116.65 (11) | C19—C18—C23 | 121.07 (12) |
| C17—N6—C24 | 113.19 (11) | C19—C18—C17 | 131.30 (12) |
| C17—N6—B1 | 122.71 (11) | C23—C18—C17 | 107.27 (11) |
| C24—N6—B1 | 122.97 (11) | C20—C19—C18 | 117.79 (12) |
| N1—C1—N2 | 122.77 (11) | C20—C19—H19A | 121.1 |
| N1—C1—C2 | 129.71 (12) | C18—C19—H19A | 121.1 |
| N2—C1—C2 | 105.62 (11) | C19—C20—C21 | 121.44 (13) |
| C3—C2—C7 | 120.10 (12) | C19—C20—H20A | 119.3 |
| C3—C2—C1 | 132.70 (12) | C21—C20—H20A | 119.3 |
| C7—C2—C1 | 106.84 (11) | C22—C21—C20 | 121.50 (13) |
| C4—C3—C2 | 118.01 (13) | C22—C21—H21A | 119.2 |
| C4—C3—H3A | 121.0 | C20—C21—H21A | 119.2 |
| C2—C3—H3A | 121.0 | C21—C22—C23 | 118.18 (12) |
| C3—C4—C5 | 121.81 (13) | C21—C22—H22A | 120.9 |
| C3—C4—H4A | 119.1 | C23—C22—H22A | 120.9 |
| C5—C4—H4A | 119.1 | C22—C23—C18 | 119.95 (12) |
| C6—C5—C4 | 120.86 (13) | C22—C23—C24 | 132.56 (12) |
| C6—C5—H5A | 119.6 | C18—C23—C24 | 107.14 (11) |
| C4—C5—H5A | 119.6 | N1—C24—N6 | 122.38 (11) |
| C5—C6—C7 | 118.30 (13) | N1—C24—C23 | 130.16 (12) |
| C5—C6—H6A | 120.9 | N6—C24—C23 | 105.55 (10) |
| C7—C6—H6A | 120.9 | C26—C25—O1 | 119.91 (12) |
| C6—C7—C2 | 120.90 (12) | C26—C25—C30 | 120.12 (12) |
| C6—C7—C8 | 131.41 (13) | O1—C25—C30 | 119.97 (11) |
| C2—C7—C8 | 107.37 (11) | C25—C26—C27 | 119.92 (14) |
| N3—C8—N2 | 123.34 (11) | C25—C26—H26A | 120.0 |
| N3—C8—C7 | 128.92 (12) | C27—C26—H26A | 120.0 |
| N2—C8—C7 | 105.94 (11) | C28—C27—C26 | 120.19 (14) |
| N3—C9—N4 | 122.13 (11) | C28—C27—H27A | 119.9 |
| N3—C9—C10 | 131.07 (11) | C26—C27—H27A | 119.9 |
| N4—C9—C10 | 105.36 (11) | C27—C28—C29 | 119.69 (14) |
| C11—C10—C15 | 120.64 (12) | C27—C28—H28A | 120.2 |
| C11—C10—C9 | 132.19 (12) | C29—C28—H28A | 120.2 |
| C15—C10—C9 | 107.16 (11) | C28—C29—C30 | 120.59 (14) |
| C12—C11—C10 | 117.91 (13) | C28—C29—H29A | 119.7 |
| C12—C11—H11A | 121.0 | C30—C29—H29A | 119.7 |
| C10—C11—H11A | 121.0 | C29—C30—C25 | 119.48 (13) |
| C11—C12—C13 | 121.42 (13) | C29—C30—H30A | 120.3 |
| C11—C12—H12A | 119.3 | C25—C30—H30A | 120.3 |
| C13—C12—H12A | 119.3 | O1—B1—N2 | 112.61 (11) |
| C14—C13—C12 | 121.53 (13) | O1—B1—N6 | 116.43 (11) |
| C14—C13—H13A | 119.2 | N2—B1—N6 | 104.58 (10) |
| C12—C13—H13A | 119.2 | O1—B1—N4 | 114.90 (11) |
| C13—C14—C15 | 117.72 (13) | N2—B1—N4 | 104.01 (10) |
| C13—C14—H14A | 121.1 | N6—B1—N4 | 102.89 (11) |
| C15—C14—H14A | 121.1 | ||
| C24—N1—C1—N2 | 8.44 (18) | C16—N5—C17—N6 | 8.23 (17) |
| C24—N1—C1—C2 | −153.51 (13) | C16—N5—C17—C18 | −154.60 (13) |
| C8—N2—C1—N1 | −153.46 (12) | C24—N6—C17—N5 | −154.54 (12) |
| B1—N2—C1—N1 | 10.81 (19) | B1—N6—C17—N5 | 13.66 (18) |
| C8—N2—C1—C2 | 12.21 (14) | C24—N6—C17—C18 | 11.84 (14) |
| B1—N2—C1—C2 | 176.49 (11) | B1—N6—C17—C18 | −179.96 (11) |
| N1—C1—C2—C3 | −16.5 (2) | N5—C17—C18—C19 | −15.1 (2) |
| N2—C1—C2—C3 | 179.24 (14) | N6—C17—C18—C19 | 179.80 (13) |
| N1—C1—C2—C7 | 156.39 (13) | N5—C17—C18—C23 | 157.89 (12) |
| N2—C1—C2—C7 | −7.92 (14) | N6—C17—C18—C23 | −7.22 (13) |
| C7—C2—C3—C4 | −0.11 (19) | C23—C18—C19—C20 | 1.68 (19) |
| C1—C2—C3—C4 | 171.97 (13) | C17—C18—C19—C20 | 173.85 (13) |
| C2—C3—C4—C5 | −0.6 (2) | C18—C19—C20—C21 | −1.9 (2) |
| C3—C4—C5—C6 | 0.3 (2) | C19—C20—C21—C22 | 0.0 (2) |
| C4—C5—C6—C7 | 0.7 (2) | C20—C21—C22—C23 | 2.18 (19) |
| C5—C6—C7—C2 | −1.5 (2) | C21—C22—C23—C18 | −2.36 (19) |
| C5—C6—C7—C8 | −174.04 (14) | C21—C22—C23—C24 | −174.66 (13) |
| C3—C2—C7—C6 | 1.2 (2) | C19—C18—C23—C22 | 0.45 (19) |
| C1—C2—C7—C6 | −172.74 (12) | C17—C18—C23—C22 | −173.39 (11) |
| C3—C2—C7—C8 | 175.34 (12) | C19—C18—C23—C24 | 174.52 (11) |
| C1—C2—C7—C8 | 1.42 (14) | C17—C18—C23—C24 | 0.68 (14) |
| C9—N3—C8—N2 | −10.55 (18) | C1—N1—C24—N6 | −6.90 (18) |
| C9—N3—C8—C7 | 151.96 (13) | C1—N1—C24—C23 | 154.97 (13) |
| C1—N2—C8—N3 | 154.57 (12) | C17—N6—C24—N1 | 154.29 (12) |
| B1—N2—C8—N3 | −9.85 (19) | B1—N6—C24—N1 | −13.87 (19) |
| C1—N2—C8—C7 | −11.36 (15) | C17—N6—C24—C23 | −11.42 (14) |
| B1—N2—C8—C7 | −175.78 (11) | B1—N6—C24—C23 | −179.58 (11) |
| C6—C7—C8—N3 | 14.1 (2) | C22—C23—C24—N1 | 15.0 (2) |
| C2—C7—C8—N3 | −159.22 (13) | C18—C23—C24—N1 | −158.06 (13) |
| C6—C7—C8—N2 | 178.95 (14) | C22—C23—C24—N6 | 179.14 (13) |
| C2—C7—C8—N2 | 5.64 (14) | C18—C23—C24—N6 | 6.12 (13) |
| C8—N3—C9—N4 | 6.63 (18) | B1—O1—C25—C26 | 89.71 (15) |
| C8—N3—C9—C10 | −157.56 (13) | B1—O1—C25—C30 | −90.34 (14) |
| C16—N4—C9—N3 | −156.21 (12) | O1—C25—C26—C27 | −179.12 (12) |
| B1—N4—C9—N3 | 17.75 (18) | C30—C25—C26—C27 | 0.9 (2) |
| C16—N4—C9—C10 | 11.49 (14) | C25—C26—C27—C28 | −0.7 (2) |
| B1—N4—C9—C10 | −174.55 (11) | C26—C27—C28—C29 | −0.1 (2) |
| N3—C9—C10—C11 | −19.3 (2) | C27—C28—C29—C30 | 0.6 (2) |
| N4—C9—C10—C11 | 174.53 (13) | C28—C29—C30—C25 | −0.4 (2) |
| N3—C9—C10—C15 | 159.29 (13) | C26—C25—C30—C29 | −0.4 (2) |
| N4—C9—C10—C15 | −6.87 (14) | O1—C25—C30—C29 | 179.69 (12) |
| C15—C10—C11—C12 | 2.48 (19) | C25—O1—B1—N2 | 176.22 (10) |
| C9—C10—C11—C12 | −179.08 (13) | C25—O1—B1—N6 | −63.00 (14) |
| C10—C11—C12—C13 | −3.3 (2) | C25—O1—B1—N4 | 57.36 (15) |
| C11—C12—C13—C14 | 0.8 (2) | C8—N2—B1—O1 | −96.40 (14) |
| C12—C13—C14—C15 | 2.46 (19) | C1—N2—B1—O1 | 100.76 (14) |
| C13—C14—C15—C10 | −3.18 (18) | C8—N2—B1—N6 | 136.25 (12) |
| C13—C14—C15—C16 | 178.71 (13) | C1—N2—B1—N6 | −26.59 (16) |
| C11—C10—C15—C14 | 0.75 (19) | C8—N2—B1—N4 | 28.64 (16) |
| C9—C10—C15—C14 | −178.05 (11) | C1—N2—B1—N4 | −134.20 (12) |
| C11—C10—C15—C16 | 179.28 (11) | C17—N6—B1—O1 | 96.10 (14) |
| C9—C10—C15—C16 | 0.48 (14) | C24—N6—B1—O1 | −96.85 (14) |
| C17—N5—C16—N4 | −7.18 (17) | C17—N6—B1—N2 | −138.93 (11) |
| C17—N5—C16—C15 | 158.90 (13) | C24—N6—B1—N2 | 28.12 (15) |
| C9—N4—C16—N5 | 158.01 (11) | C17—N6—B1—N4 | −30.50 (15) |
| B1—N4—C16—N5 | −15.89 (18) | C24—N6—B1—N4 | 136.55 (11) |
| C9—N4—C16—C15 | −11.20 (14) | C9—N4—B1—O1 | 90.86 (14) |
| B1—N4—C16—C15 | 174.90 (11) | C16—N4—B1—O1 | −95.77 (14) |
| C14—C15—C16—N5 | 16.5 (2) | C9—N4—B1—N2 | −32.70 (15) |
| C10—C15—C16—N5 | −161.76 (13) | C16—N4—B1—N2 | 140.67 (11) |
| C14—C15—C16—N4 | −175.64 (13) | C9—N4—B1—N6 | −141.56 (11) |
| C10—C15—C16—N4 | 6.07 (13) | C16—N4—B1—N6 | 31.80 (15) |
(Naphthalen-2-olato)(subphthalocyaninato)boron (d23108a_a) top
Crystal data top
| C34H19BN6O | Dx = 1.445 Mg m−3 |
| Mr = 538.36 | Mo Kα radiation, λ = 0.71073 Å |
| Orthorhombic, Pnma | Cell parameters from 2369 reflections |
| a = 17.133 (3) Å | θ = 2.4–25.5° |
| b = 13.929 (2) Å | µ = 0.09 mm−1 |
| c = 10.3669 (16) Å | T = 150 K |
| V = 2474.0 (7) Å3 | Shard, pink |
| Z = 4 | 0.26 × 0.15 × 0.08 mm |
| F(000) = 1112 |
Data collection top
| Bruker Kappa APEX-DUO CMOS PHOTON II diffractometer | 1878 reflections with I > 2σ(I) |
| Radiation source: sealed tube with Bruker Triumph monochromator | Rint = 0.092 |
| φ and ω scans | θmax = 27.5°, θmin = 2.3° |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −21→22 |
| Tmin = 0.609, Tmax = 0.746 | k = −12→18 |
| 17347 measured reflections | l = −13→13 |
| 2963 independent reflections |
Refinement top
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.052 | H-atom parameters constrained |
| wR(F2) = 0.119 | w = 1/[σ2(Fo2) + (0.0341P)2 + 0.9945P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.05 | (Δ/σ)max < 0.001 |
| 2963 reflections | Δρmax = 0.26 e Å−3 |
| 217 parameters | Δρmin = −0.28 e Å−3 |
| 0 restraints |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | Occ. (<1) | |
| O1 | 0.59212 (11) | 0.250000 | 0.05723 (17) | 0.0314 (5) | |
| N1 | 0.57797 (12) | 0.250000 | 0.2966 (2) | 0.0192 (5) | |
| N2 | 0.59624 (9) | 0.08455 (11) | 0.34594 (14) | 0.0225 (4) | |
| N3 | 0.68267 (9) | 0.16555 (10) | 0.20190 (14) | 0.0206 (4) | |
| N4 | 0.80024 (13) | 0.250000 | 0.1556 (2) | 0.0235 (5) | |
| C1 | 0.43709 (11) | 0.19995 (15) | 0.66531 (18) | 0.0280 (5) | |
| H1 | 0.411493 | 0.166663 | 0.733194 | 0.034* | |
| C2 | 0.47342 (10) | 0.14803 (15) | 0.56894 (18) | 0.0252 (4) | |
| H2 | 0.473573 | 0.079829 | 0.569892 | 0.030* | |
| C3 | 0.50988 (10) | 0.19921 (13) | 0.47016 (17) | 0.0204 (4) | |
| C4 | 0.55865 (11) | 0.16829 (13) | 0.36331 (17) | 0.0206 (4) | |
| C5 | 0.66114 (11) | 0.08664 (13) | 0.27245 (17) | 0.0210 (4) | |
| C6 | 0.72892 (11) | 0.02434 (13) | 0.27627 (17) | 0.0233 (4) | |
| C7 | 0.74262 (12) | −0.06215 (14) | 0.34004 (19) | 0.0287 (5) | |
| H7A | 0.701759 | −0.094351 | 0.384388 | 0.034* | |
| C8 | 0.81729 (13) | −0.09982 (15) | 0.3370 (2) | 0.0335 (5) | |
| H8A | 0.827620 | −0.158970 | 0.379338 | 0.040* | |
| C9 | 0.87772 (13) | −0.05256 (16) | 0.2730 (2) | 0.0359 (5) | |
| H9A | 0.928086 | −0.081037 | 0.270487 | 0.043* | |
| C10 | 0.86578 (12) | 0.03504 (15) | 0.2129 (2) | 0.0308 (5) | |
| H10A | 0.907557 | 0.067706 | 0.171646 | 0.037* | |
| C11 | 0.79093 (11) | 0.07398 (14) | 0.21471 (18) | 0.0249 (4) | |
| C12 | 0.76111 (11) | 0.16782 (13) | 0.17731 (16) | 0.0223 (4) | |
| C13 | 0.45932 (13) | 0.30777 (14) | 0.0242 (2) | 0.0255 (9) | 0.5 |
| H13 | 0.474810 | 0.373095 | 0.030414 | 0.031* | 0.5 |
| C14 | 0.51433 (10) | 0.23520 (18) | 0.03849 (18) | 0.0211 (10) | 0.5 |
| C15 | 0.49167 (12) | 0.13962 (16) | 0.0294 (2) | 0.0296 (10) | 0.5 |
| H15 | 0.529267 | 0.090016 | 0.039168 | 0.036* | 0.5 |
| C16 | 0.41400 (14) | 0.11661 (13) | 0.0060 (2) | 0.0324 (10) | 0.5 |
| H16 | 0.398511 | 0.051288 | −0.000158 | 0.039* | 0.5 |
| C17 | 0.35899 (10) | 0.18919 (16) | −0.00823 (14) | 0.0240 (11) | 0.5 |
| C18 | 0.38165 (11) | 0.28477 (15) | 0.00085 (13) | 0.0221 (12) | 0.5 |
| C19 | 0.32664 (16) | 0.35734 (19) | −0.0134 (2) | 0.0326 (12) | 0.5 |
| H19 | 0.342132 | 0.422667 | −0.007226 | 0.039* | 0.5 |
| C20 | 0.24897 (15) | 0.3343 (3) | −0.0368 (2) | 0.0317 (15) | 0.5 |
| H20 | 0.211375 | 0.383944 | −0.046552 | 0.038* | 0.5 |
| C21 | 0.22631 (10) | 0.2388 (3) | −0.04587 (19) | 0.0407 (14) | 0.5 |
| H21 | 0.173223 | 0.223042 | −0.061839 | 0.049* | 0.5 |
| C22 | 0.28132 (11) | 0.1662 (2) | −0.0316 (2) | 0.0388 (17) | 0.5 |
| H22 | 0.265826 | 0.100863 | −0.037800 | 0.047* | 0.5 |
| B1 | 0.63003 (17) | 0.250000 | 0.1813 (3) | 0.0205 (7) |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0203 (11) | 0.0549 (13) | 0.0189 (9) | 0.000 | 0.0012 (8) | 0.000 |
| N1 | 0.0167 (12) | 0.0221 (11) | 0.0189 (11) | 0.000 | 0.0000 (9) | 0.000 |
| N2 | 0.0212 (8) | 0.0235 (9) | 0.0227 (8) | −0.0005 (7) | 0.0014 (7) | −0.0016 (7) |
| N3 | 0.0211 (9) | 0.0222 (8) | 0.0186 (8) | −0.0002 (7) | 0.0031 (7) | −0.0005 (6) |
| N4 | 0.0249 (12) | 0.0259 (12) | 0.0196 (11) | 0.000 | 0.0023 (10) | 0.000 |
| C1 | 0.0210 (10) | 0.0447 (12) | 0.0184 (9) | −0.0031 (9) | 0.0023 (8) | 0.0035 (9) |
| C2 | 0.0183 (10) | 0.0331 (11) | 0.0243 (10) | −0.0023 (9) | −0.0001 (8) | 0.0046 (9) |
| C3 | 0.0148 (9) | 0.0282 (10) | 0.0183 (9) | −0.0010 (8) | −0.0008 (7) | 0.0009 (7) |
| C4 | 0.0188 (10) | 0.0225 (10) | 0.0206 (9) | −0.0026 (8) | −0.0021 (8) | 0.0010 (8) |
| C5 | 0.0246 (10) | 0.0202 (9) | 0.0182 (9) | −0.0017 (8) | −0.0008 (8) | −0.0023 (8) |
| C6 | 0.0270 (11) | 0.0227 (10) | 0.0202 (10) | 0.0014 (8) | 0.0026 (8) | −0.0030 (8) |
| C7 | 0.0356 (12) | 0.0235 (10) | 0.0269 (10) | 0.0012 (9) | 0.0030 (9) | −0.0004 (8) |
| C8 | 0.0435 (14) | 0.0271 (11) | 0.0298 (11) | 0.0114 (10) | 0.0003 (10) | 0.0018 (9) |
| C9 | 0.0339 (13) | 0.0426 (13) | 0.0311 (12) | 0.0160 (10) | 0.0050 (10) | 0.0018 (10) |
| C10 | 0.0264 (11) | 0.0361 (12) | 0.0299 (11) | 0.0045 (9) | 0.0060 (9) | 0.0006 (9) |
| C11 | 0.0278 (11) | 0.0278 (10) | 0.0192 (9) | 0.0040 (9) | 0.0028 (9) | −0.0017 (8) |
| C12 | 0.0224 (11) | 0.0282 (11) | 0.0163 (9) | 0.0014 (8) | 0.0032 (8) | −0.0021 (7) |
| C13 | 0.031 (2) | 0.022 (2) | 0.023 (2) | −0.0020 (18) | −0.0011 (18) | −0.0026 (17) |
| C14 | 0.0255 (17) | 0.024 (3) | 0.0142 (14) | 0.0002 (18) | 0.0016 (12) | 0.0006 (17) |
| C15 | 0.033 (3) | 0.035 (3) | 0.020 (2) | −0.001 (2) | −0.0028 (18) | 0.0035 (19) |
| C16 | 0.045 (3) | 0.028 (2) | 0.025 (2) | −0.010 (2) | 0.003 (2) | 0.0016 (17) |
| C17 | 0.025 (3) | 0.026 (3) | 0.021 (2) | −0.018 (2) | 0.0038 (19) | −0.0007 (19) |
| C18 | 0.022 (2) | 0.027 (3) | 0.0172 (19) | 0.0052 (18) | 0.0000 (17) | −0.0003 (14) |
| C19 | 0.024 (3) | 0.049 (3) | 0.025 (2) | −0.008 (3) | −0.002 (2) | −0.010 (2) |
| C20 | 0.034 (4) | 0.044 (3) | 0.018 (2) | 0.006 (3) | 0.0035 (19) | −0.008 (2) |
| C21 | 0.0253 (19) | 0.074 (4) | 0.0224 (16) | −0.030 (4) | 0.0011 (14) | −0.008 (4) |
| C22 | 0.037 (5) | 0.057 (4) | 0.022 (3) | −0.012 (3) | 0.007 (2) | −0.005 (3) |
| B1 | 0.0187 (16) | 0.0232 (16) | 0.0195 (15) | 0.000 | 0.0022 (12) | 0.000 |
Geometric parameters (Å, º) top
| O1—C14 | 1.362 (2) | C8—H8A | 0.9500 |
| O1—B1 | 1.441 (3) | C9—C10 | 1.385 (3) |
| N1—C4 | 1.372 (2) | C9—H9A | 0.9500 |
| N1—C4i | 1.372 (2) | C10—C11 | 1.393 (3) |
| N1—B1 | 1.491 (4) | C10—H10A | 0.9500 |
| N2—C4 | 1.345 (2) | C11—C12 | 1.456 (3) |
| N2—C5 | 1.348 (2) | C13—C14 | 1.3900 |
| N3—C12 | 1.368 (2) | C13—C18 | 1.3900 |
| N3—C5 | 1.371 (2) | C13—H13 | 0.9500 |
| N3—B1 | 1.498 (2) | C14—C15 | 1.3900 |
| N4—C12i | 1.345 (2) | C15—C16 | 1.3900 |
| N4—C12 | 1.345 (2) | C15—H15 | 0.9500 |
| C1—C2 | 1.382 (3) | C16—C17 | 1.3900 |
| C1—C1i | 1.394 (4) | C16—H16 | 0.9500 |
| C1—H1 | 0.9500 | C17—C18 | 1.3900 |
| C2—C3 | 1.395 (3) | C17—C22 | 1.3900 |
| C2—H2 | 0.9500 | C18—C19 | 1.3900 |
| C3—C3i | 1.415 (4) | C19—C20 | 1.3900 |
| C3—C4 | 1.453 (3) | C19—H19 | 0.9500 |
| C5—C6 | 1.450 (3) | C20—C21 | 1.3900 |
| C6—C7 | 1.394 (3) | C20—H20 | 0.9500 |
| C6—C11 | 1.419 (3) | C21—C22 | 1.3900 |
| C7—C8 | 1.383 (3) | C21—H21 | 0.9500 |
| C7—H7A | 0.9500 | C22—H22 | 0.9500 |
| C8—C9 | 1.395 (3) | ||
| C14—O1—B1 | 124.61 (19) | C6—C11—C12 | 107.13 (16) |
| C4—N1—C4i | 112.1 (2) | N4—C12—N3 | 122.70 (17) |
| C4—N1—B1 | 123.23 (11) | N4—C12—C11 | 129.31 (18) |
| C4i—N1—B1 | 123.24 (11) | N3—C12—C11 | 105.91 (16) |
| C4—N2—C5 | 116.88 (15) | C14—C13—C18 | 120.0 |
| C12—N3—C5 | 112.48 (15) | C14—C13—H13 | 120.0 |
| C12—N3—B1 | 123.15 (16) | C18—C13—H13 | 120.0 |
| C5—N3—B1 | 122.93 (16) | O1—C14—C13 | 124.63 (16) |
| C12i—N4—C12 | 116.6 (2) | O1—C14—C15 | 115.33 (16) |
| C2—C1—C1i | 121.57 (12) | C13—C14—C15 | 120.0 |
| C2—C1—H1 | 119.2 | C14—C15—C16 | 120.0 |
| C1i—C1—H1 | 119.2 | C14—C15—H15 | 120.0 |
| C1—C2—C3 | 117.70 (19) | C16—C15—H15 | 120.0 |
| C1—C2—H2 | 121.1 | C15—C16—C17 | 120.0 |
| C3—C2—H2 | 121.1 | C15—C16—H16 | 120.0 |
| C2—C3—C3i | 120.73 (11) | C17—C16—H16 | 120.0 |
| C2—C3—C4 | 131.72 (18) | C18—C17—C16 | 120.0 |
| C3i—C3—C4 | 107.25 (10) | C18—C17—C22 | 120.0 |
| N2—C4—N1 | 122.45 (17) | C16—C17—C22 | 120.0 |
| N2—C4—C3 | 129.41 (17) | C17—C18—C19 | 120.0 |
| N1—C4—C3 | 106.08 (16) | C17—C18—C13 | 120.0 |
| N2—C5—N3 | 122.73 (16) | C19—C18—C13 | 120.0 |
| N2—C5—C6 | 129.21 (16) | C20—C19—C18 | 120.0 |
| N3—C5—C6 | 106.19 (16) | C20—C19—H19 | 120.0 |
| C7—C6—C11 | 120.55 (18) | C18—C19—H19 | 120.0 |
| C7—C6—C5 | 131.67 (18) | C19—C20—C21 | 120.0 |
| C11—C6—C5 | 107.19 (16) | C19—C20—H20 | 120.0 |
| C8—C7—C6 | 118.21 (19) | C21—C20—H20 | 120.0 |
| C8—C7—H7A | 120.9 | C20—C21—C22 | 120.0 |
| C6—C7—H7A | 120.9 | C20—C21—H21 | 120.0 |
| C7—C8—C9 | 121.21 (19) | C22—C21—H21 | 120.0 |
| C7—C8—H8A | 119.4 | C21—C22—C17 | 120.0 |
| C9—C8—H8A | 119.4 | C21—C22—H22 | 120.0 |
| C10—C9—C8 | 121.34 (19) | C17—C22—H22 | 120.0 |
| C10—C9—H9A | 119.3 | O1—B1—N1 | 116.5 (2) |
| C8—C9—H9A | 119.3 | O1—B1—N3i | 113.48 (15) |
| C9—C10—C11 | 118.25 (19) | N1—B1—N3i | 104.25 (15) |
| C9—C10—H10A | 120.9 | O1—B1—N3 | 113.48 (15) |
| C11—C10—H10A | 120.9 | N1—B1—N3 | 104.25 (15) |
| C10—C11—C6 | 120.37 (18) | N3i—B1—N3 | 103.5 (2) |
| C10—C11—C12 | 132.01 (19) | ||
| C1i—C1—C2—C3 | −0.5 (2) | C6—C11—C12—N4 | 156.1 (2) |
| C1—C2—C3—C3i | 0.5 (2) | C10—C11—C12—N3 | −179.3 (2) |
| C1—C2—C3—C4 | 173.30 (19) | C6—C11—C12—N3 | −7.52 (19) |
| C5—N2—C4—N1 | 8.7 (3) | B1—O1—C14—C13 | 96.59 (13) |
| C5—N2—C4—C3 | −152.58 (18) | B1—O1—C14—C15 | −85.63 (15) |
| C4i—N1—C4—N2 | −153.68 (13) | C18—C13—C14—O1 | 177.68 (17) |
| B1—N1—C4—N2 | 13.0 (3) | C18—C13—C14—C15 | 0.0 |
| C4i—N1—C4—C3 | 11.4 (3) | O1—C14—C15—C16 | −177.89 (16) |
| B1—N1—C4—C3 | 178.0 (2) | C13—C14—C15—C16 | 0.0 |
| C2—C3—C4—N2 | −16.5 (3) | C14—C15—C16—C17 | 0.0 |
| C3i—C3—C4—N2 | 157.01 (17) | C15—C16—C17—C18 | 0.0 |
| C2—C3—C4—N1 | 179.88 (19) | C15—C16—C17—C22 | 180.0 |
| C3i—C3—C4—N1 | −6.62 (16) | C16—C17—C18—C19 | 180.0 |
| C4—N2—C5—N3 | −9.7 (3) | C22—C17—C18—C19 | 0.0 |
| C4—N2—C5—C6 | 152.53 (18) | C16—C17—C18—C13 | 0.0 |
| C12—N3—C5—N2 | 155.83 (17) | C22—C17—C18—C13 | 180.0 |
| B1—N3—C5—N2 | −10.9 (3) | C14—C13—C18—C17 | 0.0 |
| C12—N3—C5—C6 | −9.90 (19) | C14—C13—C18—C19 | 180.0 |
| B1—N3—C5—C6 | −176.59 (17) | C17—C18—C19—C20 | 0.0 |
| N2—C5—C6—C7 | 11.1 (3) | C13—C18—C19—C20 | 180.0 |
| N3—C5—C6—C7 | 175.57 (19) | C18—C19—C20—C21 | 0.0 |
| N2—C5—C6—C11 | −159.89 (18) | C19—C20—C21—C22 | 0.0 |
| N3—C5—C6—C11 | 4.58 (19) | C20—C21—C22—C17 | 0.0 |
| C11—C6—C7—C8 | −2.6 (3) | C18—C17—C22—C21 | 0.0 |
| C5—C6—C7—C8 | −172.59 (19) | C16—C17—C22—C21 | 180.0 |
| C6—C7—C8—C9 | 0.5 (3) | C14—O1—B1—N1 | −10.60 (13) |
| C7—C8—C9—C10 | 1.7 (3) | C14—O1—B1—N3i | −131.68 (19) |
| C8—C9—C10—C11 | −1.8 (3) | C14—O1—B1—N3 | 110.5 (2) |
| C9—C10—C11—C6 | −0.2 (3) | C4—N1—B1—O1 | 97.41 (19) |
| C9—C10—C11—C12 | 170.6 (2) | C4i—N1—B1—O1 | −97.41 (19) |
| C7—C6—C11—C10 | 2.5 (3) | C4—N1—B1—N3i | −136.73 (18) |
| C5—C6—C11—C10 | 174.69 (17) | C4i—N1—B1—N3i | 28.5 (3) |
| C7—C6—C11—C12 | −170.40 (17) | C4—N1—B1—N3 | −28.5 (3) |
| C5—C6—C11—C12 | 1.8 (2) | C4i—N1—B1—N3 | 136.72 (18) |
| C12i—N4—C12—N3 | 9.3 (3) | C12—N3—B1—O1 | 94.4 (2) |
| C12i—N4—C12—C11 | −151.92 (15) | C5—N3—B1—O1 | −100.4 (2) |
| C5—N3—C12—N4 | −154.01 (18) | C12—N3—B1—N1 | −137.90 (17) |
| B1—N3—C12—N4 | 12.6 (3) | C5—N3—B1—N1 | 27.4 (2) |
| C5—N3—C12—C11 | 10.98 (19) | C12—N3—B1—N3i | −29.1 (3) |
| B1—N3—C12—C11 | 177.64 (18) | C5—N3—B1—N3i | 136.18 (15) |
| C10—C11—C12—N4 | −15.6 (3) |
| Symmetry code: (i) x, −y+1/2, z. |
(Acetato)(subphthalocyaninato)boron (d22121a_a) top
Crystal data top
| C26H15BN6O2 | Z = 2 |
| Mr = 454.25 | F(000) = 468 |
| Triclinic, P1 | Dx = 1.472 Mg m−3 |
| a = 9.3432 (9) Å | Mo Kα radiation, λ = 0.71073 Å |
| b = 9.3548 (7) Å | Cell parameters from 6060 reflections |
| c = 12.3322 (12) Å | θ = 2.5–26.8° |
| α = 104.203 (2)° | µ = 0.10 mm−1 |
| β = 100.751 (3)° | T = 150 K |
| γ = 90.701 (2)° | Shard, purple |
| V = 1024.69 (16) Å3 | 0.24 × 0.22 × 0.13 mm |
Data collection top
| Bruker Kappa APEX-DUO CMOS PHOTON II diffractometer | 3665 reflections with I > 2σ(I) |
| Radiation source: sealed tube with Bruker Triumph monochromator | Rint = 0.038 |
| φ and ω scans | θmax = 27.5°, θmin = 2.3° |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −12→12 |
| Tmin = 0.710, Tmax = 0.746 | k = −12→11 |
| 21123 measured reflections | l = −16→15 |
| 4670 independent reflections |
Refinement top
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
| wR(F2) = 0.096 | w = 1/[σ2(Fo2) + (0.0473P)2 + 0.293P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.03 | (Δ/σ)max = 0.002 |
| 4670 reflections | Δρmax = 0.32 e Å−3 |
| 317 parameters | Δρmin = −0.28 e Å−3 |
| 0 restraints |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.51457 (9) | 0.16222 (10) | 0.42428 (8) | 0.0180 (2) | |
| O2 | 0.33335 (11) | 0.11501 (11) | 0.27076 (8) | 0.0266 (2) | |
| N1 | 0.73832 (11) | 0.31198 (12) | 0.46314 (9) | 0.0164 (2) | |
| N2 | 0.90693 (12) | 0.12760 (12) | 0.42234 (9) | 0.0181 (2) | |
| N3 | 0.68811 (12) | 0.13099 (12) | 0.28825 (9) | 0.0171 (2) | |
| N4 | 0.55469 (12) | 0.20043 (12) | 0.12679 (9) | 0.0185 (2) | |
| N5 | 0.55739 (11) | 0.34670 (11) | 0.31392 (9) | 0.0161 (2) | |
| N6 | 0.64703 (12) | 0.54978 (12) | 0.47176 (9) | 0.0175 (2) | |
| C1 | 0.73959 (14) | 0.45890 (14) | 0.51425 (11) | 0.0171 (3) | |
| C2 | 0.87244 (14) | 0.49059 (14) | 0.60151 (11) | 0.0178 (3) | |
| C3 | 0.92841 (15) | 0.61748 (15) | 0.68630 (11) | 0.0210 (3) | |
| H3A | 0.877122 | 0.705362 | 0.695344 | 0.025* | |
| C4 | 1.06085 (15) | 0.61146 (16) | 0.75680 (12) | 0.0232 (3) | |
| H4A | 1.099424 | 0.695948 | 0.816275 | 0.028* | |
| C5 | 1.13944 (15) | 0.48379 (16) | 0.74260 (12) | 0.0230 (3) | |
| H5A | 1.229956 | 0.483405 | 0.792646 | 0.028* | |
| C6 | 1.08749 (14) | 0.35795 (15) | 0.65680 (11) | 0.0202 (3) | |
| H6A | 1.142441 | 0.272578 | 0.646052 | 0.024* | |
| C7 | 0.95253 (14) | 0.36032 (14) | 0.58689 (11) | 0.0176 (3) | |
| C8 | 0.86760 (14) | 0.25015 (14) | 0.49070 (11) | 0.0172 (3) | |
| C9 | 0.82094 (14) | 0.07573 (14) | 0.31928 (11) | 0.0179 (3) | |
| C10 | 0.85492 (14) | −0.01303 (14) | 0.21341 (11) | 0.0188 (3) | |
| C11 | 0.96888 (15) | −0.10341 (15) | 0.18993 (12) | 0.0233 (3) | |
| H11A | 1.042170 | −0.119308 | 0.249708 | 0.028* | |
| C12 | 0.97183 (16) | −0.16921 (16) | 0.07677 (13) | 0.0285 (3) | |
| H12A | 1.046424 | −0.234067 | 0.059297 | 0.034* | |
| C13 | 0.86795 (16) | −0.14265 (16) | −0.01232 (13) | 0.0280 (3) | |
| H13A | 0.873896 | −0.188946 | −0.088928 | 0.034* | |
| C14 | 0.75651 (15) | −0.05006 (15) | 0.00910 (12) | 0.0220 (3) | |
| H14A | 0.688062 | −0.029366 | −0.051605 | 0.026* | |
| C15 | 0.74784 (14) | 0.01171 (14) | 0.12215 (11) | 0.0186 (3) | |
| C16 | 0.64749 (14) | 0.11331 (14) | 0.17299 (11) | 0.0177 (3) | |
| C17 | 0.51454 (14) | 0.31884 (14) | 0.19836 (11) | 0.0173 (3) | |
| C18 | 0.45372 (14) | 0.45407 (14) | 0.17736 (11) | 0.0187 (3) | |
| C19 | 0.38252 (15) | 0.48801 (16) | 0.07794 (12) | 0.0224 (3) | |
| H19A | 0.361657 | 0.414911 | 0.007488 | 0.027* | |
| C20 | 0.34312 (17) | 0.63161 (17) | 0.08506 (13) | 0.0283 (3) | |
| H20A | 0.294024 | 0.657104 | 0.018336 | 0.034* | |
| C21 | 0.37395 (17) | 0.73993 (17) | 0.18817 (13) | 0.0297 (3) | |
| H21A | 0.345795 | 0.837585 | 0.189952 | 0.036* | |
| C22 | 0.44477 (15) | 0.70809 (15) | 0.28805 (12) | 0.0241 (3) | |
| H22A | 0.465685 | 0.782615 | 0.357717 | 0.029* | |
| C23 | 0.48448 (14) | 0.56374 (14) | 0.28350 (11) | 0.0186 (3) | |
| C24 | 0.56196 (14) | 0.49317 (14) | 0.36891 (11) | 0.0171 (3) | |
| C25 | 0.37765 (14) | 0.11811 (14) | 0.37020 (11) | 0.0181 (3) | |
| C26 | 0.28623 (15) | 0.07167 (16) | 0.44437 (13) | 0.0241 (3) | |
| H26A | 0.183080 | 0.082274 | 0.414825 | 0.036* | |
| H26B | 0.314413 | 0.134049 | 0.522317 | 0.036* | |
| H26C | 0.301221 | −0.031754 | 0.444617 | 0.036* | |
| B1 | 0.61638 (15) | 0.23270 (16) | 0.37237 (12) | 0.0162 (3) |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0147 (4) | 0.0206 (5) | 0.0201 (5) | 0.0018 (4) | 0.0038 (4) | 0.0073 (4) |
| O2 | 0.0264 (5) | 0.0315 (5) | 0.0198 (5) | −0.0057 (4) | 0.0001 (4) | 0.0064 (4) |
| N1 | 0.0158 (5) | 0.0186 (5) | 0.0159 (5) | 0.0029 (4) | 0.0041 (4) | 0.0053 (4) |
| N2 | 0.0183 (5) | 0.0189 (5) | 0.0182 (6) | 0.0025 (4) | 0.0041 (4) | 0.0063 (4) |
| N3 | 0.0152 (5) | 0.0180 (5) | 0.0181 (6) | 0.0017 (4) | 0.0029 (4) | 0.0048 (4) |
| N4 | 0.0157 (5) | 0.0204 (6) | 0.0191 (6) | 0.0010 (4) | 0.0030 (4) | 0.0046 (4) |
| N5 | 0.0143 (5) | 0.0180 (5) | 0.0159 (5) | 0.0014 (4) | 0.0029 (4) | 0.0042 (4) |
| N6 | 0.0163 (5) | 0.0206 (6) | 0.0165 (6) | 0.0031 (4) | 0.0048 (4) | 0.0049 (4) |
| C1 | 0.0172 (6) | 0.0190 (6) | 0.0166 (6) | 0.0014 (5) | 0.0061 (5) | 0.0049 (5) |
| C2 | 0.0158 (6) | 0.0230 (7) | 0.0165 (6) | 0.0014 (5) | 0.0047 (5) | 0.0075 (5) |
| C3 | 0.0227 (7) | 0.0209 (7) | 0.0198 (7) | 0.0010 (5) | 0.0051 (5) | 0.0049 (5) |
| C4 | 0.0228 (7) | 0.0247 (7) | 0.0198 (7) | −0.0035 (5) | 0.0028 (6) | 0.0025 (6) |
| C5 | 0.0159 (6) | 0.0326 (8) | 0.0201 (7) | −0.0009 (5) | 0.0009 (5) | 0.0076 (6) |
| C6 | 0.0166 (6) | 0.0257 (7) | 0.0196 (7) | 0.0035 (5) | 0.0043 (5) | 0.0077 (5) |
| C7 | 0.0170 (6) | 0.0220 (6) | 0.0159 (6) | 0.0009 (5) | 0.0058 (5) | 0.0067 (5) |
| C8 | 0.0158 (6) | 0.0198 (6) | 0.0179 (6) | 0.0020 (5) | 0.0039 (5) | 0.0080 (5) |
| C9 | 0.0168 (6) | 0.0179 (6) | 0.0209 (7) | 0.0024 (5) | 0.0052 (5) | 0.0073 (5) |
| C10 | 0.0188 (6) | 0.0167 (6) | 0.0205 (7) | −0.0003 (5) | 0.0043 (5) | 0.0038 (5) |
| C11 | 0.0207 (7) | 0.0222 (7) | 0.0261 (7) | 0.0036 (5) | 0.0048 (6) | 0.0040 (6) |
| C12 | 0.0235 (7) | 0.0284 (8) | 0.0311 (8) | 0.0065 (6) | 0.0090 (6) | −0.0001 (6) |
| C13 | 0.0281 (8) | 0.0294 (8) | 0.0229 (7) | 0.0013 (6) | 0.0084 (6) | −0.0029 (6) |
| C14 | 0.0212 (7) | 0.0228 (7) | 0.0195 (7) | −0.0020 (5) | 0.0033 (5) | 0.0014 (5) |
| C15 | 0.0174 (6) | 0.0175 (6) | 0.0200 (7) | −0.0013 (5) | 0.0037 (5) | 0.0032 (5) |
| C16 | 0.0161 (6) | 0.0194 (6) | 0.0164 (6) | −0.0017 (5) | 0.0017 (5) | 0.0033 (5) |
| C17 | 0.0137 (6) | 0.0212 (6) | 0.0172 (6) | 0.0000 (5) | 0.0022 (5) | 0.0060 (5) |
| C18 | 0.0150 (6) | 0.0226 (7) | 0.0196 (7) | 0.0030 (5) | 0.0047 (5) | 0.0064 (5) |
| C19 | 0.0215 (7) | 0.0277 (7) | 0.0180 (7) | 0.0050 (6) | 0.0035 (5) | 0.0060 (6) |
| C20 | 0.0308 (8) | 0.0338 (8) | 0.0224 (7) | 0.0124 (6) | 0.0034 (6) | 0.0121 (6) |
| C21 | 0.0364 (9) | 0.0261 (8) | 0.0282 (8) | 0.0129 (6) | 0.0046 (7) | 0.0105 (6) |
| C22 | 0.0264 (7) | 0.0230 (7) | 0.0221 (7) | 0.0057 (6) | 0.0044 (6) | 0.0043 (6) |
| C23 | 0.0152 (6) | 0.0234 (7) | 0.0186 (7) | 0.0038 (5) | 0.0044 (5) | 0.0066 (5) |
| C24 | 0.0156 (6) | 0.0190 (6) | 0.0185 (6) | 0.0031 (5) | 0.0065 (5) | 0.0058 (5) |
| C25 | 0.0172 (6) | 0.0147 (6) | 0.0217 (7) | 0.0024 (5) | 0.0033 (5) | 0.0033 (5) |
| C26 | 0.0189 (7) | 0.0282 (7) | 0.0267 (8) | 0.0004 (5) | 0.0048 (6) | 0.0098 (6) |
| B1 | 0.0148 (7) | 0.0183 (7) | 0.0158 (7) | 0.0021 (5) | 0.0031 (6) | 0.0046 (6) |
Geometric parameters (Å, º) top
| O1—C25 | 1.3362 (15) | C7—C8 | 1.4587 (18) |
| O1—B1 | 1.4725 (17) | C9—C10 | 1.4573 (18) |
| O2—C25 | 1.2120 (16) | C10—C11 | 1.3962 (18) |
| N1—C1 | 1.3631 (17) | C10—C15 | 1.4264 (19) |
| N1—C8 | 1.3673 (16) | C11—C12 | 1.386 (2) |
| N1—B1 | 1.4823 (18) | C11—H11A | 0.9500 |
| N2—C9 | 1.3428 (17) | C12—C13 | 1.397 (2) |
| N2—C8 | 1.3460 (17) | C12—H12A | 0.9500 |
| N3—C16 | 1.3689 (17) | C13—C14 | 1.384 (2) |
| N3—C9 | 1.3746 (16) | C13—H13A | 0.9500 |
| N3—B1 | 1.4904 (17) | C14—C15 | 1.3900 (19) |
| N4—C17 | 1.3419 (17) | C14—H14A | 0.9500 |
| N4—C16 | 1.3421 (17) | C15—C16 | 1.4574 (18) |
| N5—C17 | 1.3644 (17) | C17—C18 | 1.4539 (18) |
| N5—C24 | 1.3678 (17) | C18—C19 | 1.3923 (18) |
| N5—B1 | 1.4846 (17) | C18—C23 | 1.4290 (19) |
| N6—C24 | 1.3435 (17) | C19—C20 | 1.384 (2) |
| N6—C1 | 1.3465 (17) | C19—H19A | 0.9500 |
| C1—C2 | 1.4569 (18) | C20—C21 | 1.397 (2) |
| C2—C3 | 1.3956 (19) | C20—H20A | 0.9500 |
| C2—C7 | 1.4292 (18) | C21—C22 | 1.387 (2) |
| C3—C4 | 1.3837 (19) | C21—H21A | 0.9500 |
| C3—H3A | 0.9500 | C22—C23 | 1.3954 (19) |
| C4—C5 | 1.401 (2) | C22—H22A | 0.9500 |
| C4—H4A | 0.9500 | C23—C24 | 1.4621 (18) |
| C5—C6 | 1.387 (2) | C25—C26 | 1.4941 (19) |
| C5—H5A | 0.9500 | C26—H26A | 0.9800 |
| C6—C7 | 1.3922 (18) | C26—H26B | 0.9800 |
| C6—H6A | 0.9500 | C26—H26C | 0.9800 |
| C25—O1—B1 | 121.85 (10) | C14—C13—H13A | 119.4 |
| C1—N1—C8 | 113.88 (11) | C12—C13—H13A | 119.4 |
| C1—N1—B1 | 122.67 (11) | C13—C14—C15 | 117.97 (13) |
| C8—N1—B1 | 122.78 (11) | C13—C14—H14A | 121.0 |
| C9—N2—C8 | 117.21 (11) | C15—C14—H14A | 121.0 |
| C16—N3—C9 | 113.09 (11) | C14—C15—C10 | 121.07 (12) |
| C16—N3—B1 | 122.79 (11) | C14—C15—C16 | 131.64 (13) |
| C9—N3—B1 | 122.33 (11) | C10—C15—C16 | 107.17 (11) |
| C17—N4—C16 | 117.15 (11) | N4—C16—N3 | 122.87 (12) |
| C17—N5—C24 | 113.67 (11) | N4—C16—C15 | 130.06 (12) |
| C17—N5—B1 | 122.88 (11) | N3—C16—C15 | 105.63 (11) |
| C24—N5—B1 | 122.73 (11) | N4—C17—N5 | 122.44 (11) |
| C24—N6—C1 | 116.91 (11) | N4—C17—C18 | 130.67 (12) |
| N6—C1—N1 | 122.65 (12) | N5—C17—C18 | 105.39 (11) |
| N6—C1—C2 | 130.98 (12) | C19—C18—C23 | 121.12 (12) |
| N1—C1—C2 | 105.26 (11) | C19—C18—C17 | 131.76 (12) |
| C3—C2—C7 | 120.43 (12) | C23—C18—C17 | 107.07 (11) |
| C3—C2—C1 | 132.35 (12) | C20—C19—C18 | 117.86 (13) |
| C7—C2—C1 | 107.20 (11) | C20—C19—H19A | 121.1 |
| C4—C3—C2 | 118.01 (13) | C18—C19—H19A | 121.1 |
| C4—C3—H3A | 121.0 | C19—C20—C21 | 121.45 (13) |
| C2—C3—H3A | 121.0 | C19—C20—H20A | 119.3 |
| C3—C4—C5 | 121.61 (13) | C21—C20—H20A | 119.3 |
| C3—C4—H4A | 119.2 | C22—C21—C20 | 121.47 (13) |
| C5—C4—H4A | 119.2 | C22—C21—H21A | 119.3 |
| C6—C5—C4 | 121.19 (13) | C20—C21—H21A | 119.3 |
| C6—C5—H5A | 119.4 | C21—C22—C23 | 118.26 (13) |
| C4—C5—H5A | 119.4 | C21—C22—H22A | 120.9 |
| C5—C6—C7 | 118.11 (12) | C23—C22—H22A | 120.9 |
| C5—C6—H6A | 120.9 | C22—C23—C18 | 119.83 (12) |
| C7—C6—H6A | 120.9 | C22—C23—C24 | 132.97 (13) |
| C6—C7—C2 | 120.60 (12) | C18—C23—C24 | 107.15 (11) |
| C6—C7—C8 | 132.30 (12) | N6—C24—N5 | 122.26 (11) |
| C2—C7—C8 | 107.08 (11) | N6—C24—C23 | 131.61 (12) |
| N2—C8—N1 | 122.27 (12) | N5—C24—C23 | 104.94 (11) |
| N2—C8—C7 | 131.19 (12) | O2—C25—O1 | 123.07 (12) |
| N1—C8—C7 | 105.13 (11) | O2—C25—C26 | 123.79 (12) |
| N2—C9—N3 | 122.59 (12) | O1—C25—C26 | 113.13 (11) |
| N2—C9—C10 | 130.32 (12) | C25—C26—H26A | 109.5 |
| N3—C9—C10 | 105.35 (11) | C25—C26—H26B | 109.5 |
| C11—C10—C15 | 120.00 (12) | H26A—C26—H26B | 109.5 |
| C11—C10—C9 | 132.66 (12) | C25—C26—H26C | 109.5 |
| C15—C10—C9 | 107.25 (11) | H26A—C26—H26C | 109.5 |
| C12—C11—C10 | 117.98 (13) | H26B—C26—H26C | 109.5 |
| C12—C11—H11A | 121.0 | O1—B1—N1 | 109.01 (11) |
| C10—C11—H11A | 121.0 | O1—B1—N5 | 116.59 (11) |
| C11—C12—C13 | 121.72 (13) | N1—B1—N5 | 104.40 (10) |
| C11—C12—H12A | 119.1 | O1—B1—N3 | 116.01 (11) |
| C13—C12—H12A | 119.1 | N1—B1—N3 | 104.83 (10) |
| C14—C13—C12 | 121.15 (13) | N5—B1—N3 | 104.79 (11) |
| C24—N6—C1—N1 | −6.98 (18) | C14—C15—C16—N4 | −16.1 (2) |
| C24—N6—C1—C2 | 159.13 (13) | C10—C15—C16—N4 | 159.94 (13) |
| C8—N1—C1—N6 | 156.87 (12) | C14—C15—C16—N3 | 177.61 (14) |
| B1—N1—C1—N6 | −13.95 (19) | C10—C15—C16—N3 | −6.33 (14) |
| C8—N1—C1—C2 | −12.30 (14) | C16—N4—C17—N5 | −4.05 (18) |
| B1—N1—C1—C2 | 176.88 (11) | C16—N4—C17—C18 | 159.85 (13) |
| N6—C1—C2—C3 | 17.4 (2) | C24—N5—C17—N4 | 153.53 (12) |
| N1—C1—C2—C3 | −174.73 (14) | B1—N5—C17—N4 | −17.04 (19) |
| N6—C1—C2—C7 | −160.90 (13) | C24—N5—C17—C18 | −13.86 (14) |
| N1—C1—C2—C7 | 7.01 (14) | B1—N5—C17—C18 | 175.56 (11) |
| C7—C2—C3—C4 | −1.65 (19) | N4—C17—C18—C19 | 20.0 (2) |
| C1—C2—C3—C4 | −179.73 (13) | N5—C17—C18—C19 | −174.03 (14) |
| C2—C3—C4—C5 | 1.6 (2) | N4—C17—C18—C23 | −157.47 (13) |
| C3—C4—C5—C6 | 0.1 (2) | N5—C17—C18—C23 | 8.48 (14) |
| C4—C5—C6—C7 | −1.9 (2) | C23—C18—C19—C20 | 0.3 (2) |
| C5—C6—C7—C2 | 1.80 (19) | C17—C18—C19—C20 | −176.87 (14) |
| C5—C6—C7—C8 | 179.83 (13) | C18—C19—C20—C21 | 0.3 (2) |
| C3—C2—C7—C6 | −0.06 (19) | C19—C20—C21—C22 | −0.3 (2) |
| C1—C2—C7—C6 | 178.45 (12) | C20—C21—C22—C23 | −0.3 (2) |
| C3—C2—C7—C8 | −178.53 (12) | C21—C22—C23—C18 | 0.9 (2) |
| C1—C2—C7—C8 | −0.02 (14) | C21—C22—C23—C24 | 178.05 (14) |
| C9—N2—C8—N1 | 6.77 (18) | C19—C18—C23—C22 | −0.9 (2) |
| C9—N2—C8—C7 | −157.61 (13) | C17—C18—C23—C22 | 176.87 (12) |
| C1—N1—C8—N2 | −155.60 (12) | C19—C18—C23—C24 | −178.75 (12) |
| B1—N1—C8—N2 | 15.20 (19) | C17—C18—C23—C24 | −0.94 (14) |
| C1—N1—C8—C7 | 12.28 (14) | C1—N6—C24—N5 | 6.48 (18) |
| B1—N1—C8—C7 | −176.91 (11) | C1—N6—C24—C23 | −159.10 (13) |
| C6—C7—C8—N2 | −18.8 (2) | C17—N5—C24—N6 | −155.67 (12) |
| C2—C7—C8—N2 | 159.41 (13) | B1—N5—C24—N6 | 14.92 (19) |
| C6—C7—C8—N1 | 174.83 (13) | C17—N5—C24—C23 | 13.22 (14) |
| C2—C7—C8—N1 | −6.95 (13) | B1—N5—C24—C23 | −176.19 (11) |
| C8—N2—C9—N3 | −8.47 (18) | C22—C23—C24—N6 | −16.9 (2) |
| C8—N2—C9—C10 | 154.20 (13) | C18—C23—C24—N6 | 160.49 (13) |
| C16—N3—C9—N2 | 153.58 (12) | C22—C23—C24—N5 | 175.67 (14) |
| B1—N3—C9—N2 | −11.54 (19) | C18—C23—C24—N5 | −6.92 (14) |
| C16—N3—C9—C10 | −12.79 (14) | B1—O1—C25—O2 | 9.79 (18) |
| B1—N3—C9—C10 | −177.91 (11) | B1—O1—C25—C26 | −170.89 (11) |
| N2—C9—C10—C11 | 19.6 (2) | C25—O1—B1—N1 | 161.53 (10) |
| N3—C9—C10—C11 | −175.47 (14) | C25—O1—B1—N5 | 43.71 (16) |
| N2—C9—C10—C15 | −156.92 (13) | C25—O1—B1—N3 | −80.48 (14) |
| N3—C9—C10—C15 | 8.00 (14) | C1—N1—B1—O1 | −95.33 (13) |
| C15—C10—C11—C12 | −1.3 (2) | C8—N1—B1—O1 | 94.66 (13) |
| C9—C10—C11—C12 | −177.50 (14) | C1—N1—B1—N5 | 29.92 (16) |
| C10—C11—C12—C13 | 2.4 (2) | C8—N1—B1—N5 | −140.08 (12) |
| C11—C12—C13—C14 | −0.6 (2) | C1—N1—B1—N3 | 139.84 (12) |
| C12—C13—C14—C15 | −2.3 (2) | C8—N1—B1—N3 | −30.16 (15) |
| C13—C14—C15—C10 | 3.3 (2) | C17—N5—B1—O1 | −100.40 (14) |
| C13—C14—C15—C16 | 178.92 (14) | C24—N5—B1—O1 | 89.87 (15) |
| C11—C10—C15—C14 | −1.5 (2) | C17—N5—B1—N1 | 139.29 (12) |
| C9—C10—C15—C14 | 175.51 (12) | C24—N5—B1—N1 | −30.43 (15) |
| C11—C10—C15—C16 | −178.11 (12) | C17—N5—B1—N3 | 29.34 (16) |
| C9—C10—C15—C16 | −1.05 (14) | C24—N5—B1—N3 | −140.38 (11) |
| C17—N4—C16—N3 | 7.59 (18) | C16—N3—B1—O1 | 104.34 (14) |
| C17—N4—C16—C15 | −156.62 (13) | C9—N3—B1—O1 | −91.99 (14) |
| C9—N3—C16—N4 | −155.35 (12) | C16—N3—B1—N1 | −135.39 (12) |
| B1—N3—C16—N4 | 9.69 (19) | C9—N3—B1—N1 | 28.29 (15) |
| C9—N3—C16—C15 | 12.16 (14) | C16—N3—B1—N5 | −25.75 (16) |
| B1—N3—C16—C15 | 177.20 (11) | C9—N3—B1—N5 | 137.92 (12) |
(Benzoato)(subphthalocyaninato)boron (d22123a_a) top
Crystal data top
| C31H17BN6O2 | F(000) = 1064 |
| Mr = 516.31 | Dx = 1.420 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| a = 15.671 (2) Å | Cell parameters from 7016 reflections |
| b = 11.1920 (13) Å | θ = 2.4–26.5° |
| c = 15.2363 (19) Å | µ = 0.09 mm−1 |
| β = 115.386 (4)° | T = 150 K |
| V = 2414.3 (5) Å3 | Shard, purple |
| Z = 4 | 0.30 × 0.15 × 0.12 mm |
Data collection top
| Bruker Kappa APEX-DUO CMOS PHOTON II diffractometer | 4050 reflections with I > 2σ(I) |
| Radiation source: sealed tube with Bruker Triumph monochromator | Rint = 0.071 |
| φ and ω scans | θmax = 27.5°, θmin = 2.4° |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −20→19 |
| Tmin = 0.685, Tmax = 0.746 | k = −14→14 |
| 49333 measured reflections | l = −18→19 |
| 5530 independent reflections |
Refinement top
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
| wR(F2) = 0.095 | w = 1/[σ2(Fo2) + (0.0424P)2 + 0.5643P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.03 | (Δ/σ)max < 0.001 |
| 5530 reflections | Δρmax = 0.23 e Å−3 |
| 361 parameters | Δρmin = −0.24 e Å−3 |
| 0 restraints |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.23861 (7) | 0.35273 (8) | 0.50040 (7) | 0.0209 (2) | |
| O2 | 0.37184 (7) | 0.41722 (9) | 0.62313 (7) | 0.0277 (2) | |
| N1 | 0.36297 (8) | 0.20804 (10) | 0.49803 (8) | 0.0187 (3) | |
| N2 | 0.46030 (8) | 0.17010 (10) | 0.66567 (8) | 0.0197 (3) | |
| N3 | 0.29257 (8) | 0.17210 (10) | 0.60497 (8) | 0.0185 (2) | |
| N4 | 0.14395 (8) | 0.07323 (10) | 0.54412 (8) | 0.0207 (3) | |
| N5 | 0.20195 (8) | 0.15311 (10) | 0.43511 (8) | 0.0183 (3) | |
| N6 | 0.28428 (8) | 0.13708 (10) | 0.33543 (8) | 0.0204 (3) | |
| C1 | 0.36234 (10) | 0.17422 (12) | 0.41122 (9) | 0.0192 (3) | |
| C2 | 0.46093 (10) | 0.15779 (12) | 0.43022 (10) | 0.0200 (3) | |
| C3 | 0.50344 (10) | 0.12818 (13) | 0.36951 (10) | 0.0232 (3) | |
| H3A | 0.467163 | 0.118337 | 0.301563 | 0.028* | |
| C4 | 0.60064 (11) | 0.11359 (13) | 0.41186 (11) | 0.0255 (3) | |
| H4A | 0.631602 | 0.096427 | 0.371656 | 0.031* | |
| C5 | 0.65433 (10) | 0.12346 (13) | 0.51222 (11) | 0.0265 (3) | |
| H5A | 0.720884 | 0.113456 | 0.538597 | 0.032* | |
| C6 | 0.61234 (10) | 0.14755 (13) | 0.57398 (11) | 0.0232 (3) | |
| H6A | 0.648565 | 0.150503 | 0.642391 | 0.028* | |
| C7 | 0.51517 (10) | 0.16730 (12) | 0.53225 (10) | 0.0202 (3) | |
| C8 | 0.44935 (10) | 0.18976 (12) | 0.57478 (10) | 0.0195 (3) | |
| C9 | 0.38098 (10) | 0.15422 (12) | 0.67778 (9) | 0.0192 (3) | |
| C10 | 0.36703 (10) | 0.08998 (12) | 0.75356 (10) | 0.0197 (3) | |
| C11 | 0.43129 (10) | 0.04217 (13) | 0.84154 (10) | 0.0232 (3) | |
| H11A | 0.496991 | 0.058001 | 0.865532 | 0.028* | |
| C12 | 0.39635 (11) | −0.02920 (14) | 0.89293 (10) | 0.0264 (3) | |
| H12A | 0.438988 | −0.062705 | 0.953114 | 0.032* | |
| C13 | 0.29967 (11) | −0.05309 (13) | 0.85826 (10) | 0.0258 (3) | |
| H13A | 0.277954 | −0.100885 | 0.896093 | 0.031* | |
| C14 | 0.23526 (10) | −0.00862 (13) | 0.77021 (10) | 0.0226 (3) | |
| H14A | 0.169858 | −0.026252 | 0.746470 | 0.027* | |
| C15 | 0.26911 (10) | 0.06298 (12) | 0.71715 (9) | 0.0199 (3) | |
| C16 | 0.22426 (10) | 0.10886 (12) | 0.61832 (10) | 0.0192 (3) | |
| C17 | 0.13748 (9) | 0.08822 (12) | 0.45387 (10) | 0.0192 (3) | |
| C18 | 0.08486 (10) | 0.01871 (13) | 0.36687 (10) | 0.0209 (3) | |
| C19 | 0.01279 (10) | −0.06518 (13) | 0.34499 (11) | 0.0250 (3) | |
| H19A | −0.016278 | −0.077976 | 0.387578 | 0.030* | |
| C20 | −0.01502 (11) | −0.12889 (14) | 0.25987 (11) | 0.0299 (4) | |
| H20A | −0.064764 | −0.185408 | 0.243152 | 0.036* | |
| C21 | 0.02850 (11) | −0.11216 (15) | 0.19734 (11) | 0.0298 (4) | |
| H21A | 0.008053 | −0.158124 | 0.139473 | 0.036* | |
| C22 | 0.10047 (10) | −0.03027 (14) | 0.21811 (10) | 0.0256 (3) | |
| H22A | 0.130006 | −0.019926 | 0.175671 | 0.031* | |
| C23 | 0.12866 (9) | 0.03695 (13) | 0.30318 (10) | 0.0207 (3) | |
| C24 | 0.20710 (10) | 0.11861 (12) | 0.35138 (9) | 0.0192 (3) | |
| C25 | 0.29049 (10) | 0.43418 (13) | 0.56571 (10) | 0.0206 (3) | |
| C26 | 0.23874 (10) | 0.54689 (12) | 0.56255 (10) | 0.0224 (3) | |
| C27 | 0.14812 (11) | 0.56741 (14) | 0.49178 (11) | 0.0305 (4) | |
| H27A | 0.117876 | 0.509561 | 0.442499 | 0.037* | |
| C28 | 0.10142 (13) | 0.67269 (15) | 0.49288 (13) | 0.0388 (4) | |
| H28A | 0.039559 | 0.687250 | 0.443944 | 0.047* | |
| C29 | 0.14523 (14) | 0.75613 (15) | 0.56536 (13) | 0.0396 (4) | |
| H29A | 0.113295 | 0.827864 | 0.566469 | 0.048* | |
| C30 | 0.23529 (13) | 0.73522 (14) | 0.63603 (12) | 0.0350 (4) | |
| H30A | 0.264859 | 0.792507 | 0.685975 | 0.042* | |
| C31 | 0.28302 (12) | 0.63147 (14) | 0.63486 (11) | 0.0280 (3) | |
| H31A | 0.345463 | 0.618190 | 0.683025 | 0.034* | |
| B1 | 0.27495 (11) | 0.22967 (14) | 0.51035 (11) | 0.0189 (3) |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0230 (5) | 0.0174 (5) | 0.0202 (5) | 0.0011 (4) | 0.0072 (4) | −0.0009 (4) |
| O2 | 0.0232 (6) | 0.0271 (6) | 0.0286 (5) | −0.0011 (4) | 0.0073 (5) | −0.0031 (4) |
| N1 | 0.0193 (6) | 0.0184 (6) | 0.0180 (6) | −0.0005 (5) | 0.0077 (5) | 0.0003 (5) |
| N2 | 0.0206 (6) | 0.0190 (6) | 0.0195 (6) | −0.0012 (5) | 0.0086 (5) | −0.0014 (5) |
| N3 | 0.0187 (6) | 0.0188 (6) | 0.0180 (6) | 0.0013 (5) | 0.0079 (5) | −0.0006 (5) |
| N4 | 0.0190 (6) | 0.0236 (6) | 0.0198 (6) | 0.0020 (5) | 0.0087 (5) | −0.0004 (5) |
| N5 | 0.0181 (6) | 0.0189 (6) | 0.0179 (6) | 0.0014 (5) | 0.0078 (5) | 0.0011 (5) |
| N6 | 0.0209 (6) | 0.0213 (6) | 0.0184 (6) | 0.0001 (5) | 0.0078 (5) | 0.0025 (5) |
| C1 | 0.0250 (8) | 0.0165 (7) | 0.0176 (7) | −0.0001 (5) | 0.0103 (6) | 0.0018 (5) |
| C2 | 0.0228 (7) | 0.0154 (7) | 0.0232 (7) | −0.0018 (5) | 0.0111 (6) | 0.0012 (6) |
| C3 | 0.0289 (8) | 0.0196 (7) | 0.0237 (7) | −0.0025 (6) | 0.0137 (6) | −0.0001 (6) |
| C4 | 0.0291 (8) | 0.0215 (8) | 0.0325 (8) | −0.0010 (6) | 0.0195 (7) | −0.0016 (6) |
| C5 | 0.0216 (8) | 0.0227 (8) | 0.0362 (8) | 0.0005 (6) | 0.0135 (7) | 0.0006 (6) |
| C6 | 0.0221 (8) | 0.0215 (8) | 0.0254 (7) | −0.0009 (6) | 0.0097 (6) | 0.0007 (6) |
| C7 | 0.0221 (7) | 0.0163 (7) | 0.0234 (7) | −0.0010 (5) | 0.0108 (6) | 0.0008 (6) |
| C8 | 0.0191 (7) | 0.0167 (7) | 0.0210 (7) | −0.0011 (5) | 0.0070 (6) | −0.0009 (5) |
| C9 | 0.0213 (7) | 0.0171 (7) | 0.0171 (6) | 0.0001 (5) | 0.0062 (6) | −0.0030 (5) |
| C10 | 0.0224 (7) | 0.0190 (7) | 0.0190 (6) | 0.0023 (6) | 0.0101 (6) | −0.0026 (6) |
| C11 | 0.0247 (8) | 0.0248 (8) | 0.0182 (7) | 0.0021 (6) | 0.0073 (6) | −0.0028 (6) |
| C12 | 0.0325 (9) | 0.0262 (8) | 0.0192 (7) | 0.0042 (6) | 0.0099 (6) | 0.0023 (6) |
| C13 | 0.0369 (9) | 0.0237 (8) | 0.0218 (7) | 0.0012 (6) | 0.0172 (7) | 0.0008 (6) |
| C14 | 0.0250 (8) | 0.0233 (8) | 0.0229 (7) | 0.0019 (6) | 0.0135 (6) | −0.0019 (6) |
| C15 | 0.0238 (7) | 0.0190 (7) | 0.0186 (6) | 0.0035 (6) | 0.0107 (6) | −0.0020 (5) |
| C16 | 0.0208 (7) | 0.0192 (7) | 0.0205 (7) | 0.0015 (6) | 0.0117 (6) | −0.0013 (6) |
| C17 | 0.0168 (7) | 0.0198 (7) | 0.0209 (7) | 0.0025 (5) | 0.0081 (6) | 0.0001 (6) |
| C18 | 0.0174 (7) | 0.0232 (8) | 0.0198 (7) | 0.0039 (6) | 0.0058 (6) | 0.0010 (6) |
| C19 | 0.0187 (7) | 0.0286 (8) | 0.0258 (7) | −0.0003 (6) | 0.0078 (6) | 0.0004 (6) |
| C20 | 0.0215 (8) | 0.0310 (9) | 0.0316 (8) | −0.0045 (6) | 0.0062 (7) | −0.0053 (7) |
| C21 | 0.0255 (8) | 0.0334 (9) | 0.0254 (7) | −0.0014 (7) | 0.0062 (7) | −0.0095 (7) |
| C22 | 0.0219 (8) | 0.0321 (9) | 0.0205 (7) | 0.0019 (6) | 0.0070 (6) | −0.0026 (6) |
| C23 | 0.0172 (7) | 0.0226 (7) | 0.0197 (7) | 0.0040 (5) | 0.0053 (6) | 0.0014 (6) |
| C24 | 0.0207 (7) | 0.0193 (7) | 0.0164 (6) | 0.0028 (5) | 0.0069 (6) | 0.0017 (5) |
| C25 | 0.0247 (8) | 0.0215 (7) | 0.0185 (7) | −0.0029 (6) | 0.0120 (6) | 0.0012 (5) |
| C26 | 0.0309 (8) | 0.0186 (7) | 0.0231 (7) | −0.0004 (6) | 0.0165 (6) | 0.0010 (6) |
| C27 | 0.0379 (9) | 0.0253 (8) | 0.0272 (8) | 0.0054 (7) | 0.0129 (7) | 0.0011 (6) |
| C28 | 0.0466 (11) | 0.0305 (9) | 0.0390 (9) | 0.0142 (8) | 0.0179 (8) | 0.0069 (8) |
| C29 | 0.0607 (12) | 0.0217 (9) | 0.0521 (11) | 0.0098 (8) | 0.0390 (10) | 0.0054 (8) |
| C30 | 0.0509 (11) | 0.0238 (8) | 0.0436 (10) | −0.0077 (7) | 0.0330 (9) | −0.0080 (7) |
| C31 | 0.0349 (9) | 0.0253 (8) | 0.0311 (8) | −0.0068 (7) | 0.0210 (7) | −0.0049 (6) |
| B1 | 0.0192 (8) | 0.0187 (8) | 0.0178 (7) | 0.0011 (6) | 0.0070 (6) | 0.0003 (6) |
Geometric parameters (Å, º) top
| O1—C25 | 1.3374 (16) | C11—C12 | 1.385 (2) |
| O1—B1 | 1.4731 (18) | C11—H11A | 0.9500 |
| O2—C25 | 1.2126 (17) | C12—C13 | 1.400 (2) |
| N1—C1 | 1.3718 (17) | C12—H12A | 0.9500 |
| N1—C8 | 1.3728 (17) | C13—C14 | 1.380 (2) |
| N1—B1 | 1.489 (2) | C13—H13A | 0.9500 |
| N2—C8 | 1.3385 (17) | C14—C15 | 1.394 (2) |
| N2—C9 | 1.3444 (18) | C14—H14A | 0.9500 |
| N3—C9 | 1.3684 (17) | C15—C16 | 1.4552 (19) |
| N3—C16 | 1.3693 (18) | C17—C18 | 1.4509 (19) |
| N3—B1 | 1.4928 (19) | C18—C19 | 1.395 (2) |
| N4—C16 | 1.3421 (18) | C18—C23 | 1.423 (2) |
| N4—C17 | 1.3453 (17) | C19—C20 | 1.377 (2) |
| N5—C24 | 1.3680 (17) | C19—H19A | 0.9500 |
| N5—C17 | 1.3702 (17) | C20—C21 | 1.402 (2) |
| N5—B1 | 1.4942 (19) | C20—H20A | 0.9500 |
| N6—C1 | 1.3385 (18) | C21—C22 | 1.381 (2) |
| N6—C24 | 1.3477 (18) | C21—H21A | 0.9500 |
| C1—C2 | 1.457 (2) | C22—C23 | 1.3964 (19) |
| C2—C3 | 1.392 (2) | C22—H22A | 0.9500 |
| C2—C7 | 1.4204 (19) | C23—C24 | 1.453 (2) |
| C3—C4 | 1.386 (2) | C25—C26 | 1.489 (2) |
| C3—H3A | 0.9500 | C26—C27 | 1.385 (2) |
| C4—C5 | 1.398 (2) | C26—C31 | 1.391 (2) |
| C4—H4A | 0.9500 | C27—C28 | 1.391 (2) |
| C5—C6 | 1.386 (2) | C27—H27A | 0.9500 |
| C5—H5A | 0.9500 | C28—C29 | 1.383 (2) |
| C6—C7 | 1.393 (2) | C28—H28A | 0.9500 |
| C6—H6A | 0.9500 | C29—C30 | 1.380 (3) |
| C7—C8 | 1.456 (2) | C29—H29A | 0.9500 |
| C9—C10 | 1.4541 (19) | C30—C31 | 1.386 (2) |
| C10—C11 | 1.3928 (19) | C30—H30A | 0.9500 |
| C10—C15 | 1.423 (2) | C31—H31A | 0.9500 |
| C25—O1—B1 | 118.41 (11) | C14—C15—C16 | 131.88 (13) |
| C1—N1—C8 | 112.15 (11) | C10—C15—C16 | 106.87 (12) |
| C1—N1—B1 | 122.83 (11) | N4—C16—N3 | 122.61 (12) |
| C8—N1—B1 | 123.04 (11) | N4—C16—C15 | 129.00 (13) |
| C8—N2—C9 | 116.60 (12) | N3—C16—C15 | 105.94 (11) |
| C9—N3—C16 | 112.85 (11) | N4—C17—N5 | 122.69 (12) |
| C9—N3—B1 | 123.36 (12) | N4—C17—C18 | 129.14 (13) |
| C16—N3—B1 | 122.27 (11) | N5—C17—C18 | 105.95 (11) |
| C16—N4—C17 | 117.16 (12) | C19—C18—C23 | 120.76 (13) |
| C24—N5—C17 | 112.86 (11) | C19—C18—C17 | 131.61 (13) |
| C24—N5—B1 | 123.06 (12) | C23—C18—C17 | 107.14 (12) |
| C17—N5—B1 | 122.30 (11) | C20—C19—C18 | 118.07 (14) |
| C1—N6—C24 | 116.81 (12) | C20—C19—H19A | 121.0 |
| N6—C1—N1 | 122.93 (12) | C18—C19—H19A | 121.0 |
| N6—C1—C2 | 129.17 (13) | C19—C20—C21 | 121.42 (14) |
| N1—C1—C2 | 105.95 (11) | C19—C20—H20A | 119.3 |
| C3—C2—C7 | 120.86 (13) | C21—C20—H20A | 119.3 |
| C3—C2—C1 | 131.84 (13) | C22—C21—C20 | 121.37 (14) |
| C7—C2—C1 | 107.10 (12) | C22—C21—H21A | 119.3 |
| C4—C3—C2 | 117.53 (13) | C20—C21—H21A | 119.3 |
| C4—C3—H3A | 121.2 | C21—C22—C23 | 118.21 (14) |
| C2—C3—H3A | 121.2 | C21—C22—H22A | 120.9 |
| C3—C4—C5 | 121.73 (14) | C23—C22—H22A | 120.9 |
| C3—C4—H4A | 119.1 | C22—C23—C18 | 120.16 (13) |
| C5—C4—H4A | 119.1 | C22—C23—C24 | 132.10 (13) |
| C6—C5—C4 | 121.29 (14) | C18—C23—C24 | 107.24 (11) |
| C6—C5—H5A | 119.4 | N6—C24—N5 | 122.76 (12) |
| C4—C5—H5A | 119.4 | N6—C24—C23 | 129.45 (12) |
| C5—C6—C7 | 117.71 (13) | N5—C24—C23 | 105.87 (11) |
| C5—C6—H6A | 121.1 | O2—C25—O1 | 123.09 (13) |
| C7—C6—H6A | 121.1 | O2—C25—C26 | 123.05 (13) |
| C6—C7—C2 | 120.77 (13) | O1—C25—C26 | 113.85 (12) |
| C6—C7—C8 | 131.94 (13) | C27—C26—C31 | 120.03 (14) |
| C2—C7—C8 | 107.12 (12) | C27—C26—C25 | 121.86 (13) |
| N2—C8—N1 | 123.23 (13) | C31—C26—C25 | 118.09 (13) |
| N2—C8—C7 | 129.12 (13) | C26—C27—C28 | 120.01 (15) |
| N1—C8—C7 | 105.94 (11) | C26—C27—H27A | 120.0 |
| N2—C9—N3 | 122.94 (12) | C28—C27—H27A | 120.0 |
| N2—C9—C10 | 129.56 (12) | C29—C28—C27 | 119.86 (16) |
| N3—C9—C10 | 105.75 (12) | C29—C28—H28A | 120.1 |
| C11—C10—C15 | 120.51 (13) | C27—C28—H28A | 120.1 |
| C11—C10—C9 | 131.41 (13) | C30—C29—C28 | 120.01 (16) |
| C15—C10—C9 | 107.44 (12) | C30—C29—H29A | 120.0 |
| C12—C11—C10 | 117.89 (14) | C28—C29—H29A | 120.0 |
| C12—C11—H11A | 121.1 | C29—C30—C31 | 120.63 (15) |
| C10—C11—H11A | 121.1 | C29—C30—H30A | 119.7 |
| C11—C12—C13 | 121.53 (13) | C31—C30—H30A | 119.7 |
| C11—C12—H12A | 119.2 | C30—C31—C26 | 119.45 (15) |
| C13—C12—H12A | 119.2 | C30—C31—H31A | 120.3 |
| C14—C13—C12 | 121.34 (14) | C26—C31—H31A | 120.3 |
| C14—C13—H13A | 119.3 | O1—B1—N1 | 118.49 (12) |
| C12—C13—H13A | 119.3 | O1—B1—N3 | 113.97 (12) |
| C13—C14—C15 | 117.99 (14) | N1—B1—N3 | 104.69 (11) |
| C13—C14—H14A | 121.0 | O1—B1—N5 | 108.79 (11) |
| C15—C14—H14A | 121.0 | N1—B1—N5 | 104.83 (11) |
| C14—C15—C10 | 120.72 (13) | N3—B1—N5 | 104.91 (11) |
| C24—N6—C1—N1 | −8.6 (2) | C24—N5—C17—N4 | 154.42 (13) |
| C24—N6—C1—C2 | 153.16 (14) | B1—N5—C17—N4 | −10.8 (2) |
| C8—N1—C1—N6 | 152.01 (13) | C24—N5—C17—C18 | −10.04 (15) |
| B1—N1—C1—N6 | −12.4 (2) | B1—N5—C17—C18 | −175.26 (12) |
| C8—N1—C1—C2 | −13.38 (15) | N4—C17—C18—C19 | 14.9 (3) |
| B1—N1—C1—C2 | −177.79 (12) | N5—C17—C18—C19 | 177.99 (14) |
| N6—C1—C2—C3 | 18.5 (2) | N4—C17—C18—C23 | −156.91 (14) |
| N1—C1—C2—C3 | −177.36 (14) | N5—C17—C18—C23 | 6.19 (15) |
| N6—C1—C2—C7 | −156.29 (14) | C23—C18—C19—C20 | −0.5 (2) |
| N1—C1—C2—C7 | 7.86 (15) | C17—C18—C19—C20 | −171.33 (15) |
| C7—C2—C3—C4 | −2.7 (2) | C18—C19—C20—C21 | 1.1 (2) |
| C1—C2—C3—C4 | −176.90 (14) | C19—C20—C21—C22 | −0.6 (2) |
| C2—C3—C4—C5 | 2.4 (2) | C20—C21—C22—C23 | −0.6 (2) |
| C3—C4—C5—C6 | 0.5 (2) | C21—C22—C23—C18 | 1.2 (2) |
| C4—C5—C6—C7 | −3.0 (2) | C21—C22—C23—C24 | 171.92 (15) |
| C5—C6—C7—C2 | 2.7 (2) | C19—C18—C23—C22 | −0.7 (2) |
| C5—C6—C7—C8 | 177.27 (14) | C17—C18—C23—C22 | 172.17 (12) |
| C3—C2—C7—C6 | 0.2 (2) | C19—C18—C23—C24 | −173.51 (13) |
| C1—C2—C7—C6 | 175.67 (13) | C17—C18—C23—C24 | −0.64 (15) |
| C3—C2—C7—C8 | −175.61 (12) | C1—N6—C24—N5 | 10.2 (2) |
| C1—C2—C7—C8 | −0.14 (15) | C1—N6—C24—C23 | −151.73 (14) |
| C9—N2—C8—N1 | 7.90 (19) | C17—N5—C24—N6 | −155.94 (13) |
| C9—N2—C8—C7 | −155.02 (14) | B1—N5—C24—N6 | 9.2 (2) |
| C1—N1—C8—N2 | −152.99 (13) | C17—N5—C24—C23 | 9.63 (15) |
| B1—N1—C8—N2 | 11.4 (2) | B1—N5—C24—C23 | 174.72 (12) |
| C1—N1—C8—C7 | 13.30 (15) | C22—C23—C24—N6 | −12.5 (3) |
| B1—N1—C8—C7 | 177.66 (12) | C18—C23—C24—N6 | 159.10 (14) |
| C6—C7—C8—N2 | −17.6 (3) | C22—C23—C24—N5 | −176.77 (15) |
| C2—C7—C8—N2 | 157.57 (14) | C18—C23—C24—N5 | −5.16 (15) |
| C6—C7—C8—N1 | 177.22 (14) | B1—O1—C25—O2 | 12.02 (19) |
| C2—C7—C8—N1 | −7.62 (15) | B1—O1—C25—C26 | −167.05 (11) |
| C8—N2—C9—N3 | −8.38 (19) | O2—C25—C26—C27 | 175.26 (14) |
| C8—N2—C9—C10 | 154.34 (14) | O1—C25—C26—C27 | −5.67 (19) |
| C16—N3—C9—N2 | 155.77 (13) | O2—C25—C26—C31 | −6.4 (2) |
| B1—N3—C9—N2 | −10.4 (2) | O1—C25—C26—C31 | 172.67 (12) |
| C16—N3—C9—C10 | −10.47 (15) | C31—C26—C27—C28 | 0.1 (2) |
| B1—N3—C9—C10 | −176.62 (12) | C25—C26—C27—C28 | 178.42 (14) |
| N2—C9—C10—C11 | 10.8 (2) | C26—C27—C28—C29 | −0.7 (2) |
| N3—C9—C10—C11 | 175.80 (14) | C27—C28—C29—C30 | 0.4 (3) |
| N2—C9—C10—C15 | −159.73 (14) | C28—C29—C30—C31 | 0.5 (2) |
| N3—C9—C10—C15 | 5.26 (15) | C29—C30—C31—C26 | −1.1 (2) |
| C15—C10—C11—C12 | −1.7 (2) | C27—C26—C31—C30 | 0.8 (2) |
| C9—C10—C11—C12 | −171.21 (14) | C25—C26—C31—C30 | −177.55 (13) |
| C10—C11—C12—C13 | 0.0 (2) | C25—O1—B1—N1 | −65.32 (16) |
| C11—C12—C13—C14 | 1.5 (2) | C25—O1—B1—N3 | 58.54 (16) |
| C12—C13—C14—C15 | −1.1 (2) | C25—O1—B1—N5 | 175.20 (11) |
| C13—C14—C15—C10 | −0.6 (2) | C1—N1—B1—O1 | −94.46 (16) |
| C13—C14—C15—C16 | 169.87 (14) | C8—N1—B1—O1 | 102.82 (15) |
| C11—C10—C15—C14 | 2.1 (2) | C1—N1—B1—N3 | 137.21 (12) |
| C9—C10—C15—C14 | 173.82 (12) | C8—N1—B1—N3 | −25.51 (17) |
| C11—C10—C15—C16 | −170.55 (12) | C1—N1—B1—N5 | 27.06 (17) |
| C9—C10—C15—C16 | 1.22 (15) | C8—N1—B1—N5 | −135.66 (12) |
| C17—N4—C16—N3 | 8.50 (19) | C9—N3—B1—O1 | −105.91 (15) |
| C17—N4—C16—C15 | −151.17 (14) | C16—N3—B1—O1 | 89.21 (15) |
| C9—N3—C16—N4 | −152.44 (13) | C9—N3—B1—N1 | 25.11 (17) |
| B1—N3—C16—N4 | 13.9 (2) | C16—N3—B1—N1 | −139.77 (12) |
| C9—N3—C16—C15 | 11.25 (15) | C9—N3—B1—N5 | 135.20 (12) |
| B1—N3—C16—C15 | 177.58 (12) | C16—N3—B1—N5 | −29.68 (17) |
| C14—C15—C16—N4 | −16.4 (3) | C24—N5—B1—O1 | 102.14 (14) |
| C10—C15—C16—N4 | 155.03 (14) | C17—N5—B1—O1 | −94.15 (14) |
| C14—C15—C16—N3 | −178.70 (14) | C24—N5—B1—N1 | −25.54 (17) |
| C10—C15—C16—N3 | −7.25 (15) | C17—N5—B1—N1 | 138.17 (12) |
| C16—N4—C17—N5 | −10.01 (19) | C24—N5—B1—N3 | −135.53 (13) |
| C16—N4—C17—C18 | 150.60 (14) | C17—N5—B1—N3 | 28.18 (16) |
(Subphthalocyaninato)(trimethylsilanolato)boron (d23117_a) top
Crystal data top
| C27H21BN6OSi | F(000) = 1008 |
| Mr = 484.40 | Dx = 1.336 Mg m−3 |
| Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
| a = 16.343 (3) Å | Cell parameters from 6743 reflections |
| b = 11.9655 (16) Å | θ = 2.8–62.7° |
| c = 12.5059 (19) Å | µ = 1.13 mm−1 |
| β = 99.996 (11)° | T = 150 K |
| V = 2408.4 (6) Å3 | Plate, pink |
| Z = 4 | 0.19 × 0.15 × 0.01 mm |
Data collection top
| Bruker Kappa APEX-DUO CMOS PHOTON II diffractometer | 2990 reflections with I > 2σ(I) |
| Radiation source: Incoatec ImuS with multi-layer optics | Rint = 0.127 |
| φ and ω scans | θmax = 69.6°, θmin = 2.8° |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −19→18 |
| Tmin = 0.629, Tmax = 0.753 | k = −14→14 |
| 57016 measured reflections | l = −14→15 |
| 4230 independent reflections |
Refinement top
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.054 | w = 1/[σ2(Fo2) + 2.7611P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.123 | (Δ/σ)max < 0.001 |
| S = 1.05 | Δρmax = 0.31 e Å−3 |
| 4230 reflections | Δρmin = −0.24 e Å−3 |
| 326 parameters | Extinction correction: SHELXL2019 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| 0 restraints | Extinction coefficient: 0.00173 (18) |
| Primary atom site location: structure-invariant direct methods |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| Si1 | 0.92196 (5) | 0.56589 (8) | 0.69390 (6) | 0.0419 (3) | |
| O1 | 0.82133 (11) | 0.58527 (17) | 0.66502 (14) | 0.0404 (5) | |
| N1 | 0.67572 (14) | 0.54454 (19) | 0.59336 (16) | 0.0315 (5) | |
| N2 | 0.61079 (13) | 0.7152 (2) | 0.62674 (16) | 0.0324 (5) | |
| N3 | 0.73048 (13) | 0.71287 (19) | 0.54058 (16) | 0.0311 (5) | |
| N4 | 0.79269 (13) | 0.7113 (2) | 0.38153 (17) | 0.0337 (5) | |
| N5 | 0.76928 (13) | 0.54202 (19) | 0.47089 (16) | 0.0315 (5) | |
| N6 | 0.69104 (15) | 0.37895 (19) | 0.49431 (17) | 0.0362 (6) | |
| C1 | 0.65420 (17) | 0.4375 (2) | 0.5652 (2) | 0.0339 (6) | |
| C2 | 0.57669 (17) | 0.4167 (2) | 0.6060 (2) | 0.0341 (7) | |
| C3 | 0.52886 (18) | 0.3214 (3) | 0.6107 (2) | 0.0383 (7) | |
| H3A | 0.544905 | 0.251917 | 0.584005 | 0.046* | |
| C4 | 0.45704 (19) | 0.3303 (3) | 0.6553 (2) | 0.0411 (7) | |
| H4A | 0.424840 | 0.265383 | 0.662027 | 0.049* | |
| C5 | 0.43160 (18) | 0.4327 (3) | 0.6903 (2) | 0.0396 (7) | |
| H5A | 0.381451 | 0.436591 | 0.718769 | 0.047* | |
| C6 | 0.47703 (17) | 0.5288 (3) | 0.6848 (2) | 0.0353 (7) | |
| H6A | 0.458409 | 0.598563 | 0.707774 | 0.042* | |
| C7 | 0.55133 (17) | 0.5207 (2) | 0.6443 (2) | 0.0321 (6) | |
| C8 | 0.61404 (16) | 0.6031 (2) | 0.62890 (19) | 0.0314 (6) | |
| C9 | 0.66603 (16) | 0.7676 (2) | 0.5752 (2) | 0.0317 (6) | |
| C10 | 0.65924 (17) | 0.8756 (2) | 0.5218 (2) | 0.0326 (6) | |
| C11 | 0.60688 (18) | 0.9665 (2) | 0.5262 (2) | 0.0365 (7) | |
| H11A | 0.568910 | 0.967777 | 0.575691 | 0.044* | |
| C12 | 0.61161 (19) | 1.0550 (2) | 0.4565 (2) | 0.0401 (7) | |
| H12A | 0.577332 | 1.118639 | 0.459568 | 0.048* | |
| C13 | 0.66574 (19) | 1.0526 (3) | 0.3817 (2) | 0.0413 (7) | |
| H13A | 0.667074 | 1.114729 | 0.334729 | 0.050* | |
| C14 | 0.71758 (18) | 0.9627 (2) | 0.3739 (2) | 0.0362 (7) | |
| H14A | 0.753403 | 0.961298 | 0.321717 | 0.043* | |
| C15 | 0.71516 (17) | 0.8744 (2) | 0.4455 (2) | 0.0324 (6) | |
| C16 | 0.75527 (16) | 0.7655 (2) | 0.4544 (2) | 0.0313 (6) | |
| C17 | 0.79452 (16) | 0.5993 (2) | 0.3877 (2) | 0.0323 (6) | |
| C18 | 0.80059 (16) | 0.5173 (2) | 0.3038 (2) | 0.0317 (6) | |
| C19 | 0.82400 (17) | 0.5265 (3) | 0.2025 (2) | 0.0356 (7) | |
| H19A | 0.844024 | 0.595257 | 0.179144 | 0.043* | |
| C20 | 0.81744 (17) | 0.4334 (3) | 0.1369 (2) | 0.0388 (7) | |
| H20A | 0.834223 | 0.437620 | 0.067973 | 0.047* | |
| C21 | 0.78666 (19) | 0.3333 (3) | 0.1699 (2) | 0.0445 (8) | |
| H21A | 0.782564 | 0.270531 | 0.122721 | 0.053* | |
| C22 | 0.76184 (19) | 0.3225 (3) | 0.2695 (2) | 0.0436 (8) | |
| H22A | 0.740326 | 0.253783 | 0.290727 | 0.052* | |
| C23 | 0.76918 (17) | 0.4151 (2) | 0.3380 (2) | 0.0355 (7) | |
| C24 | 0.74429 (17) | 0.4358 (2) | 0.4426 (2) | 0.0341 (6) | |
| C25 | 0.9463 (2) | 0.5487 (4) | 0.8434 (3) | 0.0847 (15) | |
| H25A | 1.006156 | 0.536694 | 0.865852 | 0.127* | |
| H25B | 0.929659 | 0.616126 | 0.878614 | 0.127* | |
| H25C | 0.915995 | 0.484114 | 0.864899 | 0.127* | |
| C26 | 0.9766 (2) | 0.6865 (3) | 0.6480 (3) | 0.0651 (10) | |
| H26A | 1.036749 | 0.674094 | 0.665679 | 0.098* | |
| H26B | 0.960095 | 0.695330 | 0.569359 | 0.098* | |
| H26C | 0.962191 | 0.754221 | 0.684696 | 0.098* | |
| C27 | 0.9503 (2) | 0.4385 (3) | 0.6252 (3) | 0.0544 (9) | |
| H27A | 1.010494 | 0.427158 | 0.642697 | 0.082* | |
| H27B | 0.921838 | 0.373842 | 0.650062 | 0.082* | |
| H27C | 0.933464 | 0.446856 | 0.546533 | 0.082* | |
| B1 | 0.7561 (2) | 0.5960 (3) | 0.5750 (2) | 0.0331 (7) |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Si1 | 0.0324 (4) | 0.0598 (6) | 0.0333 (4) | 0.0051 (4) | 0.0054 (3) | −0.0022 (4) |
| O1 | 0.0334 (11) | 0.0576 (14) | 0.0303 (10) | 0.0052 (9) | 0.0057 (8) | −0.0006 (9) |
| N1 | 0.0350 (13) | 0.0335 (14) | 0.0271 (11) | 0.0026 (10) | 0.0087 (9) | 0.0015 (10) |
| N2 | 0.0349 (13) | 0.0374 (15) | 0.0259 (11) | −0.0005 (11) | 0.0081 (9) | −0.0009 (10) |
| N3 | 0.0335 (12) | 0.0363 (14) | 0.0256 (11) | −0.0018 (11) | 0.0107 (9) | −0.0024 (10) |
| N4 | 0.0321 (13) | 0.0387 (15) | 0.0309 (12) | −0.0056 (11) | 0.0075 (10) | −0.0026 (10) |
| N5 | 0.0330 (12) | 0.0370 (14) | 0.0262 (11) | 0.0019 (10) | 0.0103 (9) | 0.0007 (10) |
| N6 | 0.0417 (14) | 0.0355 (14) | 0.0335 (12) | 0.0050 (11) | 0.0129 (10) | 0.0027 (10) |
| C1 | 0.0389 (16) | 0.0339 (17) | 0.0295 (14) | 0.0029 (13) | 0.0077 (12) | 0.0060 (12) |
| C2 | 0.0365 (15) | 0.0395 (18) | 0.0268 (13) | −0.0001 (13) | 0.0071 (11) | 0.0063 (12) |
| C3 | 0.0463 (18) | 0.0412 (18) | 0.0290 (14) | −0.0059 (14) | 0.0109 (13) | 0.0017 (12) |
| C4 | 0.0462 (18) | 0.047 (2) | 0.0307 (15) | −0.0111 (15) | 0.0087 (13) | 0.0020 (13) |
| C5 | 0.0350 (16) | 0.054 (2) | 0.0306 (14) | −0.0046 (15) | 0.0076 (12) | 0.0016 (14) |
| C6 | 0.0374 (16) | 0.0428 (18) | 0.0266 (13) | −0.0004 (14) | 0.0080 (12) | 0.0025 (12) |
| C7 | 0.0331 (15) | 0.0392 (17) | 0.0240 (13) | −0.0006 (13) | 0.0053 (11) | 0.0050 (12) |
| C8 | 0.0336 (15) | 0.0386 (18) | 0.0231 (12) | 0.0026 (13) | 0.0079 (11) | 0.0014 (12) |
| C9 | 0.0312 (14) | 0.0393 (17) | 0.0248 (13) | −0.0019 (13) | 0.0054 (11) | −0.0046 (12) |
| C10 | 0.0379 (16) | 0.0341 (17) | 0.0264 (13) | −0.0054 (13) | 0.0070 (11) | −0.0034 (11) |
| C11 | 0.0420 (17) | 0.0374 (18) | 0.0313 (14) | −0.0001 (14) | 0.0093 (12) | −0.0042 (12) |
| C12 | 0.0514 (18) | 0.0325 (17) | 0.0365 (15) | 0.0016 (14) | 0.0080 (13) | −0.0044 (13) |
| C13 | 0.0546 (19) | 0.0342 (18) | 0.0351 (15) | −0.0077 (15) | 0.0081 (14) | −0.0007 (13) |
| C14 | 0.0458 (17) | 0.0363 (17) | 0.0277 (14) | −0.0092 (14) | 0.0100 (12) | −0.0032 (12) |
| C15 | 0.0376 (16) | 0.0319 (16) | 0.0286 (14) | −0.0076 (13) | 0.0078 (12) | −0.0054 (12) |
| C16 | 0.0313 (15) | 0.0379 (17) | 0.0264 (13) | −0.0060 (12) | 0.0096 (11) | −0.0044 (12) |
| C17 | 0.0277 (14) | 0.0382 (18) | 0.0314 (14) | −0.0018 (12) | 0.0059 (11) | 0.0004 (12) |
| C18 | 0.0296 (14) | 0.0407 (17) | 0.0257 (13) | 0.0029 (12) | 0.0078 (11) | −0.0018 (12) |
| C19 | 0.0308 (15) | 0.0437 (18) | 0.0327 (14) | 0.0023 (13) | 0.0063 (12) | 0.0006 (13) |
| C20 | 0.0370 (16) | 0.050 (2) | 0.0303 (14) | 0.0008 (14) | 0.0071 (12) | −0.0061 (13) |
| C21 | 0.0472 (19) | 0.048 (2) | 0.0400 (16) | 0.0010 (15) | 0.0128 (14) | −0.0132 (14) |
| C22 | 0.0446 (18) | 0.0393 (19) | 0.0496 (18) | −0.0023 (14) | 0.0154 (15) | −0.0062 (14) |
| C23 | 0.0349 (15) | 0.0380 (18) | 0.0351 (14) | 0.0018 (13) | 0.0108 (12) | 0.0002 (12) |
| C24 | 0.0363 (15) | 0.0345 (17) | 0.0336 (14) | 0.0047 (13) | 0.0121 (12) | 0.0030 (12) |
| C25 | 0.047 (2) | 0.162 (5) | 0.044 (2) | 0.030 (3) | 0.0036 (16) | −0.001 (2) |
| C26 | 0.048 (2) | 0.063 (3) | 0.083 (3) | −0.0077 (18) | 0.0090 (19) | −0.014 (2) |
| C27 | 0.0458 (19) | 0.058 (2) | 0.059 (2) | 0.0088 (17) | 0.0087 (16) | 0.0019 (17) |
| B1 | 0.0326 (17) | 0.040 (2) | 0.0282 (15) | −0.0019 (15) | 0.0078 (13) | 0.0004 (14) |
Geometric parameters (Å, º) top
| Si1—O1 | 1.638 (2) | C10—C11 | 1.391 (4) |
| Si1—C26 | 1.840 (4) | C10—C15 | 1.431 (4) |
| Si1—C27 | 1.847 (3) | C11—C12 | 1.382 (4) |
| Si1—C25 | 1.855 (3) | C11—H11A | 0.9500 |
| O1—B1 | 1.415 (4) | C12—C13 | 1.394 (4) |
| N1—C1 | 1.358 (3) | C12—H12A | 0.9500 |
| N1—C8 | 1.364 (3) | C13—C14 | 1.384 (4) |
| N1—B1 | 1.504 (4) | C13—H13A | 0.9500 |
| N2—C8 | 1.342 (3) | C14—C15 | 1.389 (4) |
| N2—C9 | 1.351 (3) | C14—H14A | 0.9500 |
| N3—C16 | 1.368 (3) | C15—C16 | 1.455 (4) |
| N3—C9 | 1.372 (3) | C17—C18 | 1.452 (4) |
| N3—B1 | 1.502 (4) | C18—C19 | 1.390 (4) |
| N4—C17 | 1.343 (3) | C18—C23 | 1.422 (4) |
| N4—C16 | 1.348 (3) | C19—C20 | 1.377 (4) |
| N5—C24 | 1.363 (4) | C19—H19A | 0.9500 |
| N5—C17 | 1.368 (3) | C20—C21 | 1.389 (4) |
| N5—B1 | 1.502 (4) | C20—H20A | 0.9500 |
| N6—C1 | 1.351 (3) | C21—C22 | 1.381 (4) |
| N6—C24 | 1.354 (3) | C21—H21A | 0.9500 |
| C1—C2 | 1.466 (4) | C22—C23 | 1.393 (4) |
| C2—C3 | 1.390 (4) | C22—H22A | 0.9500 |
| C2—C7 | 1.420 (4) | C23—C24 | 1.457 (4) |
| C3—C4 | 1.388 (4) | C25—H25A | 0.9800 |
| C3—H3A | 0.9500 | C25—H25B | 0.9800 |
| C4—C5 | 1.389 (4) | C25—H25C | 0.9800 |
| C4—H4A | 0.9500 | C26—H26A | 0.9800 |
| C5—C6 | 1.377 (4) | C26—H26B | 0.9800 |
| C5—H5A | 0.9500 | C26—H26C | 0.9800 |
| C6—C7 | 1.397 (4) | C27—H27A | 0.9800 |
| C6—H6A | 0.9500 | C27—H27B | 0.9800 |
| C7—C8 | 1.459 (4) | C27—H27C | 0.9800 |
| C9—C10 | 1.451 (4) | ||
| O1—Si1—C26 | 110.09 (15) | C13—C14—C15 | 117.4 (3) |
| O1—Si1—C27 | 109.70 (14) | C13—C14—H14A | 121.3 |
| C26—Si1—C27 | 109.14 (17) | C15—C14—H14A | 121.3 |
| O1—Si1—C25 | 105.64 (14) | C14—C15—C10 | 121.0 (3) |
| C26—Si1—C25 | 111.7 (2) | C14—C15—C16 | 131.9 (2) |
| C27—Si1—C25 | 110.48 (19) | C10—C15—C16 | 106.8 (2) |
| B1—O1—Si1 | 141.00 (18) | N4—C16—N3 | 122.9 (2) |
| C1—N1—C8 | 113.3 (2) | N4—C16—C15 | 129.0 (2) |
| C1—N1—B1 | 122.7 (2) | N3—C16—C15 | 106.4 (2) |
| C8—N1—B1 | 123.6 (2) | N4—C17—N5 | 122.5 (2) |
| C8—N2—C9 | 116.5 (2) | N4—C17—C18 | 129.5 (2) |
| C16—N3—C9 | 112.2 (2) | N5—C17—C18 | 106.2 (2) |
| C16—N3—B1 | 123.3 (2) | C19—C18—C23 | 120.9 (3) |
| C9—N3—B1 | 123.0 (2) | C19—C18—C17 | 132.0 (3) |
| C17—N4—C16 | 116.7 (2) | C23—C18—C17 | 106.9 (2) |
| C24—N5—C17 | 112.7 (2) | C20—C19—C18 | 118.3 (3) |
| C24—N5—B1 | 123.0 (2) | C20—C19—H19A | 120.8 |
| C17—N5—B1 | 123.5 (2) | C18—C19—H19A | 120.8 |
| C1—N6—C24 | 116.7 (2) | C19—C20—C21 | 121.0 (3) |
| N6—C1—N1 | 122.3 (2) | C19—C20—H20A | 119.5 |
| N6—C1—C2 | 130.6 (3) | C21—C20—H20A | 119.5 |
| N1—C1—C2 | 105.7 (2) | C22—C21—C20 | 121.8 (3) |
| C3—C2—C7 | 120.3 (2) | C22—C21—H21A | 119.1 |
| C3—C2—C1 | 132.8 (3) | C20—C21—H21A | 119.1 |
| C7—C2—C1 | 106.8 (2) | C21—C22—C23 | 118.2 (3) |
| C4—C3—C2 | 118.4 (3) | C21—C22—H22A | 120.9 |
| C4—C3—H3A | 120.8 | C23—C22—H22A | 120.9 |
| C2—C3—H3A | 120.8 | C22—C23—C18 | 119.8 (2) |
| C3—C4—C5 | 120.9 (3) | C22—C23—C24 | 132.8 (3) |
| C3—C4—H4A | 119.5 | C18—C23—C24 | 107.2 (2) |
| C5—C4—H4A | 119.5 | N6—C24—N5 | 122.2 (2) |
| C6—C5—C4 | 121.9 (3) | N6—C24—C23 | 130.3 (3) |
| C6—C5—H5A | 119.1 | N5—C24—C23 | 105.9 (2) |
| C4—C5—H5A | 119.1 | Si1—C25—H25A | 109.5 |
| C5—C6—C7 | 118.0 (3) | Si1—C25—H25B | 109.5 |
| C5—C6—H6A | 121.0 | H25A—C25—H25B | 109.5 |
| C7—C6—H6A | 121.0 | Si1—C25—H25C | 109.5 |
| C6—C7—C2 | 120.4 (3) | H25A—C25—H25C | 109.5 |
| C6—C7—C8 | 132.5 (3) | H25B—C25—H25C | 109.5 |
| C2—C7—C8 | 107.1 (2) | Si1—C26—H26A | 109.5 |
| N2—C8—N1 | 122.4 (2) | Si1—C26—H26B | 109.5 |
| N2—C8—C7 | 130.7 (2) | H26A—C26—H26B | 109.5 |
| N1—C8—C7 | 105.7 (2) | Si1—C26—H26C | 109.5 |
| N2—C9—N3 | 122.8 (2) | H26A—C26—H26C | 109.5 |
| N2—C9—C10 | 129.0 (2) | H26B—C26—H26C | 109.5 |
| N3—C9—C10 | 106.3 (2) | Si1—C27—H27A | 109.5 |
| C11—C10—C15 | 120.1 (3) | Si1—C27—H27B | 109.5 |
| C11—C10—C9 | 132.6 (2) | H27A—C27—H27B | 109.5 |
| C15—C10—C9 | 106.9 (2) | Si1—C27—H27C | 109.5 |
| C12—C11—C10 | 118.2 (3) | H27A—C27—H27C | 109.5 |
| C12—C11—H11A | 120.9 | H27B—C27—H27C | 109.5 |
| C10—C11—H11A | 120.9 | O1—B1—N3 | 116.5 (2) |
| C11—C12—C13 | 121.2 (3) | O1—B1—N5 | 116.7 (2) |
| C11—C12—H12A | 119.4 | N3—B1—N5 | 103.1 (2) |
| C13—C12—H12A | 119.4 | O1—B1—N1 | 113.5 (2) |
| C14—C13—C12 | 122.0 (3) | N3—B1—N1 | 102.6 (2) |
| C14—C13—H13A | 119.0 | N5—B1—N1 | 102.5 (2) |
| C12—C13—H13A | 119.0 | ||
| C26—Si1—O1—B1 | 65.4 (4) | C9—N3—C16—C15 | 11.8 (3) |
| C27—Si1—O1—B1 | −54.7 (4) | B1—N3—C16—C15 | 177.9 (2) |
| C25—Si1—O1—B1 | −173.8 (3) | C14—C15—C16—N4 | −15.2 (5) |
| C24—N6—C1—N1 | −7.2 (4) | C10—C15—C16—N4 | 158.2 (3) |
| C24—N6—C1—C2 | 156.9 (3) | C14—C15—C16—N3 | 179.9 (3) |
| C8—N1—C1—N6 | 155.7 (2) | C10—C15—C16—N3 | −6.7 (3) |
| B1—N1—C1—N6 | −17.9 (4) | C16—N4—C17—N5 | −7.8 (4) |
| C8—N1—C1—C2 | −11.9 (3) | C16—N4—C17—C18 | 154.7 (3) |
| B1—N1—C1—C2 | 174.5 (2) | C24—N5—C17—N4 | 155.2 (2) |
| N6—C1—C2—C3 | 20.3 (5) | B1—N5—C17—N4 | −14.6 (4) |
| N1—C1—C2—C3 | −173.5 (3) | C24—N5—C17—C18 | −10.9 (3) |
| N6—C1—C2—C7 | −158.6 (3) | B1—N5—C17—C18 | 179.3 (2) |
| N1—C1—C2—C7 | 7.6 (3) | N4—C17—C18—C19 | 16.2 (5) |
| C7—C2—C3—C4 | −1.1 (4) | N5—C17—C18—C19 | −179.1 (3) |
| C1—C2—C3—C4 | −179.9 (3) | N4—C17—C18—C23 | −158.4 (3) |
| C2—C3—C4—C5 | 2.7 (4) | N5—C17—C18—C23 | 6.3 (3) |
| C3—C4—C5—C6 | −1.6 (4) | C23—C18—C19—C20 | −1.2 (4) |
| C4—C5—C6—C7 | −1.1 (4) | C17—C18—C19—C20 | −175.2 (3) |
| C5—C6—C7—C2 | 2.6 (4) | C18—C19—C20—C21 | 1.3 (4) |
| C5—C6—C7—C8 | −179.0 (3) | C19—C20—C21—C22 | −0.3 (5) |
| C3—C2—C7—C6 | −1.5 (4) | C20—C21—C22—C23 | −0.7 (5) |
| C1—C2—C7—C6 | 177.6 (2) | C21—C22—C23—C18 | 0.8 (4) |
| C3—C2—C7—C8 | 179.8 (2) | C21—C22—C23—C24 | 174.9 (3) |
| C1—C2—C7—C8 | −1.2 (3) | C19—C18—C23—C22 | 0.2 (4) |
| C9—N2—C8—N1 | 7.9 (4) | C17—C18—C23—C22 | 175.5 (3) |
| C9—N2—C8—C7 | −157.9 (3) | C19—C18—C23—C24 | −175.4 (2) |
| C1—N1—C8—N2 | −157.7 (2) | C17—C18—C23—C24 | 0.0 (3) |
| B1—N1—C8—N2 | 15.9 (4) | C1—N6—C24—N5 | 9.2 (4) |
| C1—N1—C8—C7 | 11.2 (3) | C1—N6—C24—C23 | −154.0 (3) |
| B1—N1—C8—C7 | −175.3 (2) | C17—N5—C24—N6 | −155.9 (2) |
| C6—C7—C8—N2 | −16.6 (5) | B1—N5—C24—N6 | 13.9 (4) |
| C2—C7—C8—N2 | 161.9 (3) | C17—N5—C24—C23 | 10.8 (3) |
| C6—C7—C8—N1 | 175.9 (3) | B1—N5—C24—C23 | −179.3 (2) |
| C2—C7—C8—N1 | −5.6 (3) | C22—C23—C24—N6 | −15.7 (5) |
| C8—N2—C9—N3 | −9.5 (4) | C18—C23—C24—N6 | 159.0 (3) |
| C8—N2—C9—C10 | 152.8 (3) | C22—C23—C24—N5 | 179.1 (3) |
| C16—N3—C9—N2 | 153.8 (2) | C18—C23—C24—N5 | −6.2 (3) |
| B1—N3—C9—N2 | −12.4 (4) | Si1—O1—B1—N3 | −96.9 (3) |
| C16—N3—C9—C10 | −12.0 (3) | Si1—O1—B1—N5 | 25.4 (5) |
| B1—N3—C9—C10 | −178.2 (2) | Si1—O1—B1—N1 | 144.3 (2) |
| N2—C9—C10—C11 | 16.4 (5) | C16—N3—B1—O1 | 100.6 (3) |
| N3—C9—C10—C11 | −179.0 (3) | C9—N3—B1—O1 | −94.8 (3) |
| N2—C9—C10—C15 | −157.5 (3) | C16—N3—B1—N5 | −28.5 (3) |
| N3—C9—C10—C15 | 7.1 (3) | C9—N3—B1—N5 | 136.1 (2) |
| C15—C10—C11—C12 | −1.0 (4) | C16—N3—B1—N1 | −134.8 (2) |
| C9—C10—C11—C12 | −174.2 (3) | C9—N3—B1—N1 | 29.9 (3) |
| C10—C11—C12—C13 | 1.6 (4) | C24—N5—B1—O1 | 92.2 (3) |
| C11—C12—C13—C14 | −0.4 (4) | C17—N5—B1—O1 | −99.1 (3) |
| C12—C13—C14—C15 | −1.3 (4) | C24—N5—B1—N3 | −138.8 (2) |
| C13—C14—C15—C10 | 1.9 (4) | C17—N5—B1—N3 | 30.0 (3) |
| C13—C14—C15—C16 | 174.5 (3) | C24—N5—B1—N1 | −32.6 (3) |
| C11—C10—C15—C14 | −0.8 (4) | C17—N5—B1—N1 | 136.2 (2) |
| C9—C10—C15—C14 | 174.0 (2) | C1—N1—B1—O1 | −92.3 (3) |
| C11—C10—C15—C16 | −175.1 (2) | C8—N1—B1—O1 | 94.8 (3) |
| C9—C10—C15—C16 | −0.3 (3) | C1—N1—B1—N3 | 141.2 (2) |
| C17—N4—C16—N3 | 9.2 (4) | C8—N1—B1—N3 | −31.8 (3) |
| C17—N4—C16—C15 | −153.6 (3) | C1—N1—B1—N5 | 34.5 (3) |
| C9—N3—C16—N4 | −154.2 (2) | C8—N1—B1—N5 | −138.5 (2) |
| B1—N3—C16—N4 | 11.9 (4) |
(2,3,4,5,6-Pentafluorobenzenethiolato)(subphthalocyaninato)boron (d23110_a) top
Crystal data top
| C30H12BF5N6S | Z = 4 |
| Mr = 594.33 | F(000) = 1200 |
| Triclinic, P1 | Dx = 1.547 Mg m−3 |
| a = 10.7010 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
| b = 11.8651 (6) Å | Cell parameters from 9956 reflections |
| c = 22.4968 (13) Å | θ = 2.7–27.4° |
| α = 95.863 (2)° | µ = 0.20 mm−1 |
| β = 92.861 (2)° | T = 150 K |
| γ = 115.433 (2)° | Shard, pink |
| V = 2552.1 (2) Å3 | 0.35 × 0.24 × 0.05 mm |
Data collection top
| Bruker Kappa APEX-DUO CMOS PHOTON II diffractometer | 7793 reflections with I > 2σ(I) |
| Radiation source: sealed tube with Bruker Triumph monochromator | Rint = 0.073 |
| φ and ω scans | θmax = 27.5°, θmin = 1.9° |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −13→13 |
| Tmin = 0.713, Tmax = 0.746 | k = −15→15 |
| 75917 measured reflections | l = −29→29 |
| 11711 independent reflections |
Refinement top
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
| wR(F2) = 0.102 | w = 1/[σ2(Fo2) + (0.0407P)2 + 0.8213P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.02 | (Δ/σ)max = 0.001 |
| 11711 reflections | Δρmax = 0.39 e Å−3 |
| 775 parameters | Δρmin = −0.30 e Å−3 |
| 0 restraints |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| S1A | 0.49981 (5) | 0.53057 (5) | 0.88589 (2) | 0.02616 (12) | |
| F1A | 0.70408 (13) | 0.72707 (11) | 0.98271 (5) | 0.0396 (3) | |
| F2A | 0.87347 (15) | 0.69748 (13) | 1.06595 (6) | 0.0555 (4) | |
| F3A | 0.86448 (16) | 0.46768 (15) | 1.07207 (6) | 0.0605 (4) | |
| F4A | 0.68146 (16) | 0.26465 (13) | 0.99579 (6) | 0.0546 (4) | |
| F5A | 0.51425 (13) | 0.29185 (11) | 0.91116 (6) | 0.0408 (3) | |
| N1A | 0.59322 (15) | 0.61609 (14) | 0.77505 (7) | 0.0215 (3) | |
| N2A | 0.73161 (16) | 0.83583 (15) | 0.80554 (7) | 0.0242 (4) | |
| N3A | 0.77455 (15) | 0.68489 (14) | 0.85414 (7) | 0.0215 (3) | |
| N4A | 0.89447 (16) | 0.55887 (15) | 0.86719 (7) | 0.0243 (4) | |
| N5A | 0.67759 (15) | 0.47455 (14) | 0.80606 (7) | 0.0215 (3) | |
| N6A | 0.54706 (15) | 0.42765 (14) | 0.71034 (7) | 0.0239 (4) | |
| C1A | 0.53955 (18) | 0.53801 (17) | 0.72171 (8) | 0.0222 (4) | |
| C2A | 0.51256 (18) | 0.61359 (18) | 0.68042 (9) | 0.0232 (4) | |
| C3A | 0.45649 (19) | 0.5861 (2) | 0.62048 (9) | 0.0279 (4) | |
| H3AA | 0.420030 | 0.502772 | 0.599805 | 0.034* | |
| C4A | 0.4556 (2) | 0.6839 (2) | 0.59199 (10) | 0.0322 (5) | |
| H4AA | 0.417881 | 0.667264 | 0.551164 | 0.039* | |
| C5A | 0.5091 (2) | 0.8069 (2) | 0.62219 (10) | 0.0322 (5) | |
| H5AA | 0.506186 | 0.871727 | 0.601473 | 0.039* | |
| C6A | 0.56586 (19) | 0.83616 (19) | 0.68124 (9) | 0.0278 (4) | |
| H6AA | 0.602715 | 0.920053 | 0.701251 | 0.033* | |
| C7A | 0.56762 (18) | 0.73904 (18) | 0.71074 (9) | 0.0241 (4) | |
| C8A | 0.63000 (19) | 0.73977 (17) | 0.76930 (8) | 0.0226 (4) | |
| C9A | 0.80774 (19) | 0.80627 (18) | 0.84451 (8) | 0.0233 (4) | |
| C10A | 0.9500 (2) | 0.88135 (18) | 0.87186 (8) | 0.0261 (4) | |
| C11A | 1.0384 (2) | 1.00860 (19) | 0.87489 (9) | 0.0320 (5) | |
| H11A | 1.005876 | 1.065382 | 0.861224 | 0.038* | |
| C12A | 1.1753 (2) | 1.0506 (2) | 0.89839 (10) | 0.0370 (5) | |
| H12A | 1.237145 | 1.137540 | 0.901278 | 0.044* | |
| C13A | 1.2244 (2) | 0.9674 (2) | 0.91794 (9) | 0.0347 (5) | |
| H13A | 1.318807 | 0.999044 | 0.934015 | 0.042* | |
| C14A | 1.1379 (2) | 0.8396 (2) | 0.91432 (9) | 0.0298 (5) | |
| H14A | 1.172164 | 0.783299 | 0.927093 | 0.036* | |
| C15A | 0.99935 (19) | 0.79625 (18) | 0.89140 (8) | 0.0252 (4) | |
| C16A | 0.88793 (19) | 0.66983 (18) | 0.87543 (8) | 0.0226 (4) | |
| C17A | 0.79314 (19) | 0.46576 (18) | 0.82956 (8) | 0.0227 (4) | |
| C18A | 0.79684 (19) | 0.35882 (17) | 0.79304 (9) | 0.0242 (4) | |
| C19A | 0.8868 (2) | 0.30175 (18) | 0.79667 (10) | 0.0292 (5) | |
| H19A | 0.957599 | 0.327545 | 0.829189 | 0.035* | |
| C20A | 0.8695 (2) | 0.20672 (19) | 0.75150 (10) | 0.0327 (5) | |
| H20A | 0.927164 | 0.164496 | 0.753782 | 0.039* | |
| C21A | 0.7686 (2) | 0.17136 (19) | 0.70237 (10) | 0.0328 (5) | |
| H21A | 0.761129 | 0.107275 | 0.671469 | 0.039* | |
| C22A | 0.6794 (2) | 0.22745 (18) | 0.69774 (9) | 0.0291 (5) | |
| H22A | 0.611713 | 0.203445 | 0.664093 | 0.035* | |
| C23A | 0.69218 (19) | 0.32043 (17) | 0.74412 (9) | 0.0244 (4) | |
| C24A | 0.62320 (18) | 0.40202 (17) | 0.75149 (8) | 0.0226 (4) | |
| C25A | 0.60524 (19) | 0.51087 (18) | 0.94308 (8) | 0.0245 (4) | |
| C26A | 0.6973 (2) | 0.61149 (19) | 0.98424 (9) | 0.0285 (4) | |
| C27A | 0.7847 (2) | 0.5979 (2) | 1.02709 (9) | 0.0352 (5) | |
| C28A | 0.7799 (2) | 0.4815 (2) | 1.03038 (9) | 0.0375 (5) | |
| C29A | 0.6884 (2) | 0.3795 (2) | 0.99165 (9) | 0.0353 (5) | |
| C30A | 0.6022 (2) | 0.39450 (19) | 0.94868 (9) | 0.0275 (4) | |
| B1A | 0.6405 (2) | 0.5772 (2) | 0.82919 (10) | 0.0219 (5) | |
| S1B | 0.05882 (5) | 0.33569 (5) | 0.26516 (2) | 0.02715 (12) | |
| F1B | 0.04317 (13) | 0.09077 (11) | 0.29706 (6) | 0.0424 (3) | |
| F2B | 0.14031 (15) | 0.04637 (13) | 0.39967 (7) | 0.0585 (4) | |
| F3B | 0.26808 (17) | 0.23581 (17) | 0.49192 (6) | 0.0701 (5) | |
| F4B | 0.30082 (17) | 0.47153 (16) | 0.47987 (7) | 0.0698 (5) | |
| F5B | 0.20496 (13) | 0.51909 (11) | 0.37741 (6) | 0.0433 (3) | |
| N1B | −0.23801 (15) | 0.23867 (14) | 0.23854 (7) | 0.0207 (3) | |
| N2B | −0.30813 (16) | 0.06499 (15) | 0.29462 (7) | 0.0254 (4) | |
| N3B | −0.15998 (15) | 0.27250 (15) | 0.34106 (7) | 0.0228 (3) | |
| N4B | −0.10216 (16) | 0.47125 (16) | 0.39815 (8) | 0.0307 (4) | |
| N5B | −0.13423 (15) | 0.44460 (14) | 0.29154 (7) | 0.0237 (4) | |
| N6B | −0.27014 (16) | 0.40254 (14) | 0.19762 (7) | 0.0249 (4) | |
| C1B | −0.29694 (19) | 0.28062 (18) | 0.19606 (8) | 0.0221 (4) | |
| C2B | −0.40868 (19) | 0.16806 (18) | 0.16220 (8) | 0.0237 (4) | |
| C3B | −0.5002 (2) | 0.1510 (2) | 0.11228 (9) | 0.0285 (4) | |
| H3BA | −0.492009 | 0.219762 | 0.091914 | 0.034* | |
| C4B | −0.6034 (2) | 0.0308 (2) | 0.09323 (9) | 0.0344 (5) | |
| H4BA | −0.665957 | 0.016571 | 0.058757 | 0.041* | |
| C5B | −0.6174 (2) | −0.0702 (2) | 0.12372 (10) | 0.0364 (5) | |
| H5BA | −0.690252 | −0.151387 | 0.109873 | 0.044* | |
| C6B | −0.5279 (2) | −0.05479 (19) | 0.17342 (9) | 0.0310 (5) | |
| H6BA | −0.538709 | −0.123884 | 0.194044 | 0.037* | |
| C7B | −0.42164 (19) | 0.06468 (18) | 0.19246 (8) | 0.0243 (4) | |
| C8B | −0.31642 (19) | 0.11382 (17) | 0.24397 (9) | 0.0228 (4) | |
| C9B | −0.23438 (19) | 0.14713 (19) | 0.34350 (9) | 0.0251 (4) | |
| C10B | −0.2379 (2) | 0.1365 (2) | 0.40754 (9) | 0.0300 (5) | |
| C11B | −0.2983 (2) | 0.0321 (2) | 0.43806 (10) | 0.0400 (6) | |
| H11B | −0.342530 | −0.051183 | 0.417192 | 0.048* | |
| C12B | −0.2910 (3) | 0.0554 (3) | 0.50023 (11) | 0.0526 (7) | |
| H12B | −0.330177 | −0.013614 | 0.522317 | 0.063* | |
| C13B | −0.2278 (3) | 0.1772 (3) | 0.53090 (11) | 0.0561 (7) | |
| H13B | −0.224288 | 0.188703 | 0.573469 | 0.067* | |
| C14B | −0.1697 (2) | 0.2822 (3) | 0.50167 (10) | 0.0437 (6) | |
| H14B | −0.128543 | 0.364963 | 0.523142 | 0.052* | |
| C15B | −0.1743 (2) | 0.2611 (2) | 0.43919 (9) | 0.0318 (5) | |
| C16B | −0.13312 (19) | 0.3478 (2) | 0.39478 (9) | 0.0274 (4) | |
| C17B | −0.11308 (19) | 0.51507 (19) | 0.34637 (9) | 0.0280 (4) | |
| C18B | −0.13774 (19) | 0.62262 (19) | 0.33445 (10) | 0.0320 (5) | |
| C19B | −0.1270 (2) | 0.7287 (2) | 0.37161 (12) | 0.0426 (6) | |
| H19B | −0.094618 | 0.743089 | 0.413044 | 0.051* | |
| C20B | −0.1650 (2) | 0.8119 (2) | 0.34621 (14) | 0.0501 (7) | |
| H20B | −0.156079 | 0.885709 | 0.370620 | 0.060* | |
| C21B | −0.2161 (2) | 0.7912 (2) | 0.28592 (13) | 0.0461 (6) | |
| H21B | −0.241384 | 0.850687 | 0.270219 | 0.055* | |
| C22B | −0.2304 (2) | 0.68553 (19) | 0.24864 (12) | 0.0376 (5) | |
| H22B | −0.266527 | 0.670671 | 0.207679 | 0.045* | |
| C23B | −0.19008 (19) | 0.60121 (18) | 0.27311 (10) | 0.0295 (5) | |
| C24B | −0.19621 (19) | 0.48072 (18) | 0.24739 (9) | 0.0247 (4) | |
| C25B | 0.12095 (18) | 0.30688 (18) | 0.33317 (9) | 0.0241 (4) | |
| C26B | 0.1063 (2) | 0.18742 (19) | 0.34126 (9) | 0.0292 (5) | |
| C27B | 0.1549 (2) | 0.1632 (2) | 0.39406 (11) | 0.0367 (5) | |
| C28B | 0.2192 (2) | 0.2582 (3) | 0.44062 (10) | 0.0426 (6) | |
| C29B | 0.2361 (2) | 0.3779 (2) | 0.43455 (10) | 0.0408 (6) | |
| C30B | 0.1874 (2) | 0.4015 (2) | 0.38137 (9) | 0.0303 (5) | |
| B1B | −0.1227 (2) | 0.3236 (2) | 0.28434 (10) | 0.0218 (5) |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1A | 0.0222 (2) | 0.0340 (3) | 0.0249 (3) | 0.0136 (2) | 0.0059 (2) | 0.0076 (2) |
| F1A | 0.0545 (8) | 0.0296 (7) | 0.0365 (7) | 0.0221 (6) | −0.0012 (6) | −0.0010 (5) |
| F2A | 0.0630 (9) | 0.0541 (9) | 0.0418 (8) | 0.0258 (8) | −0.0208 (7) | −0.0145 (7) |
| F3A | 0.0809 (11) | 0.0797 (11) | 0.0376 (8) | 0.0549 (9) | −0.0187 (7) | 0.0003 (7) |
| F4A | 0.0915 (11) | 0.0470 (8) | 0.0410 (8) | 0.0453 (8) | −0.0020 (7) | 0.0093 (7) |
| F5A | 0.0473 (8) | 0.0287 (7) | 0.0396 (8) | 0.0117 (6) | −0.0016 (6) | 0.0015 (6) |
| N1A | 0.0187 (8) | 0.0230 (9) | 0.0233 (9) | 0.0094 (7) | 0.0035 (7) | 0.0040 (7) |
| N2A | 0.0221 (8) | 0.0252 (9) | 0.0260 (9) | 0.0118 (7) | 0.0035 (7) | −0.0001 (7) |
| N3A | 0.0220 (8) | 0.0253 (9) | 0.0182 (8) | 0.0114 (7) | 0.0028 (6) | 0.0025 (7) |
| N4A | 0.0260 (8) | 0.0287 (9) | 0.0202 (9) | 0.0128 (8) | 0.0046 (7) | 0.0070 (7) |
| N5A | 0.0195 (8) | 0.0230 (8) | 0.0213 (9) | 0.0078 (7) | 0.0044 (6) | 0.0064 (7) |
| N6A | 0.0191 (8) | 0.0237 (9) | 0.0251 (9) | 0.0054 (7) | 0.0024 (7) | 0.0048 (7) |
| C1A | 0.0166 (9) | 0.0242 (10) | 0.0225 (10) | 0.0057 (8) | 0.0019 (8) | 0.0038 (8) |
| C2A | 0.0167 (9) | 0.0290 (11) | 0.0257 (11) | 0.0106 (8) | 0.0045 (8) | 0.0071 (8) |
| C3A | 0.0203 (10) | 0.0346 (12) | 0.0283 (11) | 0.0116 (9) | 0.0006 (8) | 0.0042 (9) |
| C4A | 0.0252 (10) | 0.0464 (14) | 0.0285 (12) | 0.0176 (10) | 0.0019 (9) | 0.0113 (10) |
| C5A | 0.0262 (11) | 0.0423 (13) | 0.0371 (13) | 0.0202 (10) | 0.0080 (9) | 0.0186 (10) |
| C6A | 0.0205 (10) | 0.0288 (11) | 0.0372 (12) | 0.0124 (9) | 0.0062 (9) | 0.0098 (9) |
| C7A | 0.0168 (9) | 0.0293 (11) | 0.0291 (11) | 0.0117 (8) | 0.0059 (8) | 0.0068 (9) |
| C8A | 0.0214 (9) | 0.0243 (10) | 0.0250 (10) | 0.0119 (8) | 0.0068 (8) | 0.0056 (8) |
| C9A | 0.0243 (10) | 0.0260 (11) | 0.0210 (10) | 0.0129 (9) | 0.0051 (8) | −0.0005 (8) |
| C10A | 0.0265 (10) | 0.0287 (11) | 0.0216 (10) | 0.0122 (9) | 0.0017 (8) | −0.0036 (8) |
| C11A | 0.0316 (11) | 0.0261 (11) | 0.0347 (12) | 0.0117 (9) | 0.0005 (9) | −0.0051 (9) |
| C12A | 0.0317 (11) | 0.0299 (12) | 0.0404 (13) | 0.0078 (10) | 0.0008 (10) | −0.0070 (10) |
| C13A | 0.0225 (10) | 0.0408 (13) | 0.0313 (12) | 0.0087 (10) | −0.0023 (9) | −0.0097 (10) |
| C14A | 0.0275 (10) | 0.0397 (13) | 0.0209 (11) | 0.0153 (10) | −0.0007 (8) | −0.0024 (9) |
| C15A | 0.0245 (10) | 0.0302 (11) | 0.0187 (10) | 0.0108 (9) | 0.0028 (8) | −0.0006 (8) |
| C16A | 0.0226 (10) | 0.0303 (11) | 0.0155 (9) | 0.0118 (9) | 0.0031 (7) | 0.0041 (8) |
| C17A | 0.0224 (10) | 0.0253 (10) | 0.0225 (10) | 0.0104 (9) | 0.0067 (8) | 0.0100 (8) |
| C18A | 0.0243 (10) | 0.0216 (10) | 0.0271 (11) | 0.0084 (8) | 0.0083 (8) | 0.0095 (8) |
| C19A | 0.0256 (10) | 0.0257 (11) | 0.0385 (12) | 0.0108 (9) | 0.0091 (9) | 0.0130 (9) |
| C20A | 0.0339 (11) | 0.0255 (11) | 0.0456 (14) | 0.0163 (10) | 0.0158 (10) | 0.0130 (10) |
| C21A | 0.0398 (12) | 0.0214 (11) | 0.0374 (13) | 0.0120 (10) | 0.0152 (10) | 0.0058 (9) |
| C22A | 0.0320 (11) | 0.0221 (11) | 0.0302 (12) | 0.0080 (9) | 0.0069 (9) | 0.0058 (9) |
| C23A | 0.0243 (10) | 0.0199 (10) | 0.0281 (11) | 0.0069 (8) | 0.0086 (8) | 0.0095 (8) |
| C24A | 0.0198 (9) | 0.0204 (10) | 0.0223 (10) | 0.0036 (8) | 0.0042 (8) | 0.0032 (8) |
| C25A | 0.0232 (10) | 0.0317 (11) | 0.0214 (10) | 0.0137 (9) | 0.0088 (8) | 0.0060 (8) |
| C26A | 0.0326 (11) | 0.0299 (11) | 0.0256 (11) | 0.0160 (10) | 0.0071 (9) | 0.0027 (9) |
| C27A | 0.0387 (12) | 0.0423 (13) | 0.0235 (11) | 0.0192 (11) | −0.0020 (9) | −0.0040 (10) |
| C28A | 0.0458 (13) | 0.0540 (15) | 0.0215 (11) | 0.0312 (12) | −0.0026 (10) | 0.0038 (10) |
| C29A | 0.0528 (14) | 0.0373 (13) | 0.0273 (12) | 0.0293 (12) | 0.0070 (10) | 0.0081 (10) |
| C30A | 0.0313 (11) | 0.0292 (11) | 0.0209 (10) | 0.0121 (9) | 0.0060 (9) | 0.0020 (9) |
| B1A | 0.0209 (10) | 0.0234 (12) | 0.0215 (11) | 0.0089 (9) | 0.0050 (9) | 0.0048 (9) |
| S1B | 0.0247 (2) | 0.0386 (3) | 0.0241 (3) | 0.0174 (2) | 0.0081 (2) | 0.0107 (2) |
| F1B | 0.0457 (8) | 0.0275 (7) | 0.0490 (8) | 0.0130 (6) | −0.0004 (6) | −0.0006 (6) |
| F2B | 0.0599 (9) | 0.0552 (9) | 0.0758 (11) | 0.0336 (8) | 0.0095 (8) | 0.0360 (8) |
| F3B | 0.0752 (11) | 0.1215 (15) | 0.0381 (9) | 0.0635 (11) | −0.0019 (7) | 0.0260 (9) |
| F4B | 0.0746 (11) | 0.0881 (12) | 0.0421 (9) | 0.0411 (10) | −0.0204 (8) | −0.0242 (8) |
| F5B | 0.0436 (7) | 0.0329 (7) | 0.0528 (9) | 0.0185 (6) | 0.0031 (6) | −0.0045 (6) |
| N1B | 0.0220 (8) | 0.0198 (8) | 0.0217 (8) | 0.0099 (7) | 0.0039 (6) | 0.0043 (7) |
| N2B | 0.0285 (9) | 0.0272 (9) | 0.0258 (9) | 0.0157 (8) | 0.0071 (7) | 0.0081 (7) |
| N3B | 0.0198 (8) | 0.0287 (9) | 0.0209 (9) | 0.0113 (7) | 0.0035 (7) | 0.0034 (7) |
| N4B | 0.0208 (8) | 0.0373 (11) | 0.0298 (10) | 0.0109 (8) | 0.0018 (7) | −0.0047 (8) |
| N5B | 0.0204 (8) | 0.0239 (9) | 0.0257 (9) | 0.0092 (7) | 0.0024 (7) | 0.0010 (7) |
| N6B | 0.0235 (8) | 0.0233 (9) | 0.0294 (9) | 0.0106 (7) | 0.0047 (7) | 0.0075 (7) |
| C1B | 0.0224 (9) | 0.0254 (10) | 0.0217 (10) | 0.0124 (8) | 0.0057 (8) | 0.0063 (8) |
| C2B | 0.0245 (10) | 0.0259 (10) | 0.0221 (10) | 0.0121 (9) | 0.0059 (8) | 0.0023 (8) |
| C3B | 0.0291 (11) | 0.0353 (12) | 0.0233 (11) | 0.0165 (10) | 0.0040 (8) | 0.0015 (9) |
| C4B | 0.0314 (11) | 0.0428 (13) | 0.0243 (11) | 0.0141 (10) | −0.0003 (9) | −0.0046 (10) |
| C5B | 0.0330 (12) | 0.0331 (12) | 0.0296 (12) | 0.0043 (10) | 0.0043 (9) | −0.0082 (10) |
| C6B | 0.0360 (12) | 0.0228 (11) | 0.0286 (12) | 0.0077 (9) | 0.0101 (9) | 0.0001 (9) |
| C7B | 0.0269 (10) | 0.0244 (10) | 0.0226 (10) | 0.0121 (9) | 0.0067 (8) | 0.0014 (8) |
| C8B | 0.0250 (10) | 0.0207 (10) | 0.0259 (11) | 0.0121 (8) | 0.0075 (8) | 0.0038 (8) |
| C9B | 0.0241 (10) | 0.0323 (11) | 0.0254 (11) | 0.0167 (9) | 0.0081 (8) | 0.0097 (9) |
| C10B | 0.0269 (10) | 0.0475 (13) | 0.0272 (11) | 0.0245 (10) | 0.0087 (9) | 0.0146 (10) |
| C11B | 0.0436 (13) | 0.0567 (15) | 0.0385 (14) | 0.0341 (12) | 0.0157 (11) | 0.0250 (11) |
| C12B | 0.0626 (17) | 0.080 (2) | 0.0411 (15) | 0.0474 (16) | 0.0236 (13) | 0.0373 (15) |
| C13B | 0.0678 (18) | 0.096 (2) | 0.0279 (14) | 0.0536 (18) | 0.0158 (13) | 0.0234 (15) |
| C14B | 0.0447 (13) | 0.0743 (18) | 0.0239 (12) | 0.0368 (13) | 0.0045 (10) | 0.0069 (12) |
| C15B | 0.0256 (10) | 0.0527 (14) | 0.0252 (11) | 0.0243 (11) | 0.0032 (9) | 0.0068 (10) |
| C16B | 0.0186 (9) | 0.0428 (13) | 0.0211 (11) | 0.0145 (9) | 0.0017 (8) | 0.0006 (9) |
| C17B | 0.0186 (9) | 0.0293 (11) | 0.0316 (12) | 0.0080 (9) | 0.0033 (8) | −0.0035 (9) |
| C18B | 0.0192 (10) | 0.0246 (11) | 0.0476 (14) | 0.0063 (9) | 0.0079 (9) | −0.0025 (10) |
| C19B | 0.0286 (11) | 0.0307 (12) | 0.0604 (16) | 0.0084 (10) | 0.0090 (11) | −0.0096 (11) |
| C20B | 0.0322 (12) | 0.0245 (12) | 0.089 (2) | 0.0108 (10) | 0.0141 (13) | −0.0098 (13) |
| C21B | 0.0287 (12) | 0.0230 (12) | 0.086 (2) | 0.0117 (10) | 0.0064 (13) | 0.0039 (12) |
| C22B | 0.0230 (10) | 0.0259 (11) | 0.0642 (16) | 0.0105 (9) | 0.0062 (10) | 0.0076 (11) |
| C23B | 0.0175 (9) | 0.0205 (10) | 0.0476 (14) | 0.0056 (8) | 0.0075 (9) | 0.0033 (9) |
| C24B | 0.0193 (9) | 0.0227 (10) | 0.0330 (12) | 0.0090 (8) | 0.0061 (8) | 0.0065 (9) |
| C25B | 0.0192 (9) | 0.0314 (11) | 0.0247 (11) | 0.0129 (9) | 0.0064 (8) | 0.0054 (9) |
| C26B | 0.0256 (10) | 0.0330 (12) | 0.0311 (12) | 0.0141 (9) | 0.0049 (9) | 0.0061 (9) |
| C27B | 0.0325 (12) | 0.0432 (14) | 0.0441 (14) | 0.0226 (11) | 0.0075 (10) | 0.0188 (11) |
| C28B | 0.0382 (13) | 0.0706 (18) | 0.0314 (13) | 0.0335 (13) | 0.0032 (10) | 0.0161 (12) |
| C29B | 0.0352 (12) | 0.0589 (16) | 0.0273 (12) | 0.0238 (12) | −0.0037 (10) | −0.0102 (11) |
| C30B | 0.0253 (10) | 0.0339 (12) | 0.0348 (12) | 0.0165 (10) | 0.0041 (9) | 0.0003 (10) |
| B1B | 0.0207 (10) | 0.0252 (12) | 0.0217 (11) | 0.0120 (9) | 0.0027 (9) | 0.0037 (9) |
Geometric parameters (Å, º) top
| S1A—C25A | 1.7679 (19) | S1B—C25B | 1.7608 (19) |
| S1A—B1A | 1.955 (2) | S1B—B1B | 1.958 (2) |
| F1A—C26A | 1.346 (2) | F1B—C26B | 1.340 (2) |
| F2A—C27A | 1.344 (2) | F2B—C27B | 1.347 (2) |
| F3A—C28A | 1.341 (2) | F3B—C28B | 1.341 (2) |
| F4A—C29A | 1.346 (2) | F4B—C29B | 1.338 (3) |
| F5A—C30A | 1.344 (2) | F5B—C30B | 1.339 (2) |
| N1A—C8A | 1.369 (2) | N1B—C1B | 1.366 (2) |
| N1A—C1A | 1.369 (2) | N1B—C8B | 1.376 (2) |
| N1A—B1A | 1.486 (3) | N1B—B1B | 1.481 (3) |
| N2A—C9A | 1.339 (2) | N2B—C8B | 1.346 (2) |
| N2A—C8A | 1.343 (2) | N2B—C9B | 1.347 (3) |
| N3A—C16A | 1.371 (2) | N3B—C9B | 1.361 (2) |
| N3A—C9A | 1.371 (2) | N3B—C16B | 1.366 (2) |
| N3A—B1A | 1.484 (3) | N3B—B1B | 1.468 (3) |
| N4A—C17A | 1.342 (2) | N4B—C17B | 1.343 (3) |
| N4A—C16A | 1.343 (2) | N4B—C16B | 1.349 (3) |
| N5A—C24A | 1.367 (2) | N5B—C17B | 1.368 (2) |
| N5A—C17A | 1.370 (2) | N5B—C24B | 1.369 (2) |
| N5A—B1A | 1.489 (3) | N5B—B1B | 1.487 (3) |
| N6A—C24A | 1.345 (2) | N6B—C1B | 1.345 (2) |
| N6A—C1A | 1.346 (2) | N6B—C24B | 1.345 (2) |
| C1A—C2A | 1.455 (3) | C1B—C2B | 1.457 (3) |
| C2A—C3A | 1.395 (3) | C2B—C3B | 1.391 (3) |
| C2A—C7A | 1.424 (3) | C2B—C7B | 1.422 (3) |
| C3A—C4A | 1.386 (3) | C3B—C4B | 1.383 (3) |
| C3A—H3AA | 0.9500 | C3B—H3BA | 0.9500 |
| C4A—C5A | 1.399 (3) | C4B—C5B | 1.397 (3) |
| C4A—H4AA | 0.9500 | C4B—H4BA | 0.9500 |
| C5A—C6A | 1.378 (3) | C5B—C6B | 1.379 (3) |
| C5A—H5AA | 0.9500 | C5B—H5BA | 0.9500 |
| C6A—C7A | 1.394 (3) | C6B—C7B | 1.389 (3) |
| C6A—H6AA | 0.9500 | C6B—H6BA | 0.9500 |
| C7A—C8A | 1.444 (3) | C7B—C8B | 1.456 (3) |
| C9A—C10A | 1.456 (3) | C9B—C10B | 1.460 (3) |
| C10A—C11A | 1.387 (3) | C10B—C11B | 1.397 (3) |
| C10A—C15A | 1.421 (3) | C10B—C15B | 1.424 (3) |
| C11A—C12A | 1.385 (3) | C11B—C12B | 1.389 (3) |
| C11A—H11A | 0.9500 | C11B—H11B | 0.9500 |
| C12A—C13A | 1.397 (3) | C12B—C13B | 1.390 (4) |
| C12A—H12A | 0.9500 | C12B—H12B | 0.9500 |
| C13A—C14A | 1.387 (3) | C13B—C14B | 1.383 (4) |
| C13A—H13A | 0.9500 | C13B—H13B | 0.9500 |
| C14A—C15A | 1.394 (3) | C14B—C15B | 1.397 (3) |
| C14A—H14A | 0.9500 | C14B—H14B | 0.9500 |
| C15A—C16A | 1.453 (3) | C15B—C16B | 1.455 (3) |
| C17A—C18A | 1.456 (3) | C17B—C18B | 1.457 (3) |
| C18A—C19A | 1.398 (3) | C18B—C19B | 1.395 (3) |
| C18A—C23A | 1.417 (3) | C18B—C23B | 1.418 (3) |
| C19A—C20A | 1.381 (3) | C19B—C20B | 1.380 (3) |
| C19A—H19A | 0.9500 | C19B—H19B | 0.9500 |
| C20A—C21A | 1.400 (3) | C20B—C21B | 1.393 (4) |
| C20A—H20A | 0.9500 | C20B—H20B | 0.9500 |
| C21A—C22A | 1.383 (3) | C21B—C22B | 1.380 (3) |
| C21A—H21A | 0.9500 | C21B—H21B | 0.9500 |
| C22A—C23A | 1.395 (3) | C22B—C23B | 1.396 (3) |
| C22A—H22A | 0.9500 | C22B—H22B | 0.9500 |
| C23A—C24A | 1.450 (3) | C23B—C24B | 1.459 (3) |
| C25A—C30A | 1.386 (3) | C25B—C30B | 1.389 (3) |
| C25A—C26A | 1.388 (3) | C25B—C26B | 1.390 (3) |
| C26A—C27A | 1.378 (3) | C26B—C27B | 1.379 (3) |
| C27A—C28A | 1.369 (3) | C27B—C28B | 1.364 (3) |
| C28A—C29A | 1.366 (3) | C28B—C29B | 1.376 (3) |
| C29A—C30A | 1.380 (3) | C29B—C30B | 1.382 (3) |
| C25A—S1A—B1A | 95.25 (9) | C25B—S1B—B1B | 100.93 (9) |
| C8A—N1A—C1A | 112.74 (15) | C1B—N1B—C8B | 112.98 (15) |
| C8A—N1A—B1A | 122.29 (16) | C1B—N1B—B1B | 123.47 (15) |
| C1A—N1A—B1A | 123.18 (15) | C8B—N1B—B1B | 121.84 (15) |
| C9A—N2A—C8A | 116.86 (16) | C8B—N2B—C9B | 116.87 (16) |
| C16A—N3A—C9A | 112.63 (15) | C9B—N3B—C16B | 114.69 (16) |
| C16A—N3A—B1A | 122.86 (16) | C9B—N3B—B1B | 122.56 (16) |
| C9A—N3A—B1A | 122.64 (15) | C16B—N3B—B1B | 122.52 (17) |
| C17A—N4A—C16A | 116.84 (15) | C17B—N4B—C16B | 117.07 (17) |
| C24A—N5A—C17A | 112.72 (15) | C17B—N5B—C24B | 113.19 (16) |
| C24A—N5A—B1A | 123.01 (15) | C17B—N5B—B1B | 122.36 (16) |
| C17A—N5A—B1A | 122.26 (16) | C24B—N5B—B1B | 122.91 (16) |
| C24A—N6A—C1A | 116.87 (16) | C1B—N6B—C24B | 116.82 (16) |
| N6A—C1A—N1A | 122.72 (16) | N6B—C1B—N1B | 122.63 (17) |
| N6A—C1A—C2A | 129.83 (17) | N6B—C1B—C2B | 130.16 (16) |
| N1A—C1A—C2A | 105.55 (16) | N1B—C1B—C2B | 105.71 (15) |
| C3A—C2A—C7A | 120.40 (18) | C3B—C2B—C7B | 120.70 (18) |
| C3A—C2A—C1A | 132.43 (18) | C3B—C2B—C1B | 132.07 (18) |
| C7A—C2A—C1A | 106.97 (16) | C7B—C2B—C1B | 107.08 (16) |
| C4A—C3A—C2A | 118.01 (19) | C4B—C3B—C2B | 117.91 (19) |
| C4A—C3A—H3AA | 121.0 | C4B—C3B—H3BA | 121.0 |
| C2A—C3A—H3AA | 121.0 | C2B—C3B—H3BA | 121.0 |
| C3A—C4A—C5A | 121.27 (19) | C3B—C4B—C5B | 121.2 (2) |
| C3A—C4A—H4AA | 119.4 | C3B—C4B—H4BA | 119.4 |
| C5A—C4A—H4AA | 119.4 | C5B—C4B—H4BA | 119.4 |
| C6A—C5A—C4A | 121.61 (19) | C6B—C5B—C4B | 121.6 (2) |
| C6A—C5A—H5AA | 119.2 | C6B—C5B—H5BA | 119.2 |
| C4A—C5A—H5AA | 119.2 | C4B—C5B—H5BA | 119.2 |
| C5A—C6A—C7A | 118.01 (19) | C5B—C6B—C7B | 118.1 (2) |
| C5A—C6A—H6AA | 121.0 | C5B—C6B—H6BA | 121.0 |
| C7A—C6A—H6AA | 121.0 | C7B—C6B—H6BA | 121.0 |
| C6A—C7A—C2A | 120.69 (18) | C6B—C7B—C2B | 120.49 (18) |
| C6A—C7A—C8A | 131.67 (19) | C6B—C7B—C8B | 131.90 (18) |
| C2A—C7A—C8A | 107.36 (16) | C2B—C7B—C8B | 107.43 (16) |
| N2A—C8A—N1A | 123.01 (16) | N2B—C8B—N1B | 122.60 (17) |
| N2A—C8A—C7A | 129.21 (17) | N2B—C8B—C7B | 130.50 (17) |
| N1A—C8A—C7A | 105.73 (16) | N1B—C8B—C7B | 105.37 (15) |
| N2A—C9A—N3A | 123.00 (17) | N2B—C9B—N3B | 122.19 (17) |
| N2A—C9A—C10A | 129.34 (18) | N2B—C9B—C10B | 131.59 (18) |
| N3A—C9A—C10A | 105.93 (16) | N3B—C9B—C10B | 104.77 (17) |
| C11A—C10A—C15A | 120.83 (18) | C11B—C10B—C15B | 120.9 (2) |
| C11A—C10A—C9A | 131.68 (18) | C11B—C10B—C9B | 131.6 (2) |
| C15A—C10A—C9A | 107.07 (17) | C15B—C10B—C9B | 107.30 (18) |
| C12A—C11A—C10A | 118.2 (2) | C12B—C11B—C10B | 117.1 (2) |
| C12A—C11A—H11A | 120.9 | C12B—C11B—H11B | 121.4 |
| C10A—C11A—H11A | 120.9 | C10B—C11B—H11B | 121.4 |
| C11A—C12A—C13A | 121.3 (2) | C11B—C12B—C13B | 121.6 (2) |
| C11A—C12A—H12A | 119.4 | C11B—C12B—H12B | 119.2 |
| C13A—C12A—H12A | 119.4 | C13B—C12B—H12B | 119.2 |
| C14A—C13A—C12A | 121.29 (19) | C14B—C13B—C12B | 122.4 (2) |
| C14A—C13A—H13A | 119.4 | C14B—C13B—H13B | 118.8 |
| C12A—C13A—H13A | 119.4 | C12B—C13B—H13B | 118.8 |
| C13A—C14A—C15A | 118.08 (19) | C13B—C14B—C15B | 117.0 (2) |
| C13A—C14A—H14A | 121.0 | C13B—C14B—H14B | 121.5 |
| C15A—C14A—H14A | 121.0 | C15B—C14B—H14B | 121.5 |
| C14A—C15A—C10A | 120.35 (19) | C14B—C15B—C10B | 120.9 (2) |
| C14A—C15A—C16A | 131.84 (18) | C14B—C15B—C16B | 131.4 (2) |
| C10A—C15A—C16A | 107.36 (16) | C10B—C15B—C16B | 107.52 (17) |
| N4A—C16A—N3A | 122.66 (17) | N4B—C16B—N3B | 122.09 (18) |
| N4A—C16A—C15A | 129.55 (16) | N4B—C16B—C15B | 131.92 (18) |
| N3A—C16A—C15A | 105.83 (16) | N3B—C16B—C15B | 104.74 (18) |
| N4A—C17A—N5A | 123.08 (16) | N4B—C17B—N5B | 122.35 (18) |
| N4A—C17A—C18A | 129.28 (16) | N4B—C17B—C18B | 130.83 (18) |
| N5A—C17A—C18A | 105.48 (16) | N5B—C17B—C18B | 105.38 (17) |
| C19A—C18A—C23A | 120.70 (18) | C19B—C18B—C23B | 120.1 (2) |
| C19A—C18A—C17A | 131.89 (18) | C19B—C18B—C17B | 132.3 (2) |
| C23A—C18A—C17A | 107.21 (16) | C23B—C18B—C17B | 107.44 (17) |
| C20A—C19A—C18A | 117.88 (19) | C20B—C19B—C18B | 117.8 (2) |
| C20A—C19A—H19A | 121.1 | C20B—C19B—H19B | 121.1 |
| C18A—C19A—H19A | 121.1 | C18B—C19B—H19B | 121.1 |
| C19A—C20A—C21A | 121.30 (19) | C19B—C20B—C21B | 122.1 (2) |
| C19A—C20A—H20A | 119.4 | C19B—C20B—H20B | 118.9 |
| C21A—C20A—H20A | 119.4 | C21B—C20B—H20B | 118.9 |
| C22A—C21A—C20A | 121.62 (19) | C22B—C21B—C20B | 121.0 (2) |
| C22A—C21A—H21A | 119.2 | C22B—C21B—H21B | 119.5 |
| C20A—C21A—H21A | 119.2 | C20B—C21B—H21B | 119.5 |
| C21A—C22A—C23A | 117.76 (19) | C21B—C22B—C23B | 117.8 (2) |
| C21A—C22A—H22A | 121.1 | C21B—C22B—H22B | 121.1 |
| C23A—C22A—H22A | 121.1 | C23B—C22B—H22B | 121.1 |
| C22A—C23A—C18A | 120.67 (17) | C22B—C23B—C18B | 121.08 (19) |
| C22A—C23A—C24A | 131.79 (18) | C22B—C23B—C24B | 131.7 (2) |
| C18A—C23A—C24A | 107.26 (16) | C18B—C23B—C24B | 107.14 (17) |
| N6A—C24A—N5A | 123.10 (16) | N6B—C24B—N5B | 122.85 (16) |
| N6A—C24A—C23A | 129.36 (17) | N6B—C24B—C23B | 130.29 (17) |
| N5A—C24A—C23A | 105.87 (15) | N5B—C24B—C23B | 105.43 (17) |
| C30A—C25A—C26A | 116.31 (18) | C30B—C25B—C26B | 116.38 (18) |
| C30A—C25A—S1A | 121.85 (15) | C30B—C25B—S1B | 122.24 (15) |
| C26A—C25A—S1A | 121.84 (15) | C26B—C25B—S1B | 121.38 (15) |
| F1A—C26A—C27A | 117.95 (18) | F1B—C26B—C27B | 117.55 (19) |
| F1A—C26A—C25A | 119.92 (17) | F1B—C26B—C25B | 120.24 (18) |
| C27A—C26A—C25A | 122.12 (19) | C27B—C26B—C25B | 122.2 (2) |
| F2A—C27A—C28A | 119.74 (19) | F2B—C27B—C28B | 119.8 (2) |
| F2A—C27A—C26A | 120.62 (19) | F2B—C27B—C26B | 120.3 (2) |
| C28A—C27A—C26A | 119.6 (2) | C28B—C27B—C26B | 119.9 (2) |
| F3A—C28A—C29A | 120.0 (2) | F3B—C28B—C27B | 120.3 (2) |
| F3A—C28A—C27A | 119.9 (2) | F3B—C28B—C29B | 119.8 (2) |
| C29A—C28A—C27A | 120.07 (19) | C27B—C28B—C29B | 119.8 (2) |
| F4A—C29A—C28A | 120.06 (19) | F4B—C29B—C28B | 119.9 (2) |
| F4A—C29A—C30A | 120.2 (2) | F4B—C29B—C30B | 120.2 (2) |
| C28A—C29A—C30A | 119.73 (19) | C28B—C29B—C30B | 119.9 (2) |
| F5A—C30A—C29A | 117.86 (18) | F5B—C30B—C29B | 118.04 (19) |
| F5A—C30A—C25A | 120.04 (17) | F5B—C30B—C25B | 120.16 (18) |
| C29A—C30A—C25A | 122.10 (19) | C29B—C30B—C25B | 121.8 (2) |
| N3A—B1A—N1A | 105.58 (15) | N3B—B1B—N1B | 105.47 (16) |
| N3A—B1A—N5A | 105.31 (15) | N3B—B1B—N5B | 105.02 (15) |
| N1A—B1A—N5A | 105.43 (15) | N1B—B1B—N5B | 105.31 (15) |
| N3A—B1A—S1A | 113.72 (14) | N3B—B1B—S1B | 111.66 (13) |
| N1A—B1A—S1A | 111.33 (13) | N1B—B1B—S1B | 113.09 (13) |
| N5A—B1A—S1A | 114.69 (14) | N5B—B1B—S1B | 115.45 (14) |
| C24A—N6A—C1A—N1A | −6.8 (3) | C24B—N6B—C1B—N1B | −8.5 (3) |
| C24A—N6A—C1A—C2A | 155.10 (18) | C24B—N6B—C1B—C2B | 155.41 (19) |
| C8A—N1A—C1A—N6A | 153.15 (17) | C8B—N1B—C1B—N6B | 154.90 (17) |
| B1A—N1A—C1A—N6A | −11.9 (3) | B1B—N1B—C1B—N6B | −10.4 (3) |
| C8A—N1A—C1A—C2A | −12.54 (19) | C8B—N1B—C1B—C2B | −12.4 (2) |
| B1A—N1A—C1A—C2A | −177.56 (15) | B1B—N1B—C1B—C2B | −177.74 (16) |
| N6A—C1A—C2A—C3A | 16.9 (3) | N6B—C1B—C2B—C3B | 17.3 (3) |
| N1A—C1A—C2A—C3A | −178.82 (19) | N1B—C1B—C2B—C3B | −176.70 (19) |
| N6A—C1A—C2A—C7A | −157.83 (18) | N6B—C1B—C2B—C7B | −158.19 (19) |
| N1A—C1A—C2A—C7A | 6.46 (19) | N1B—C1B—C2B—C7B | 7.80 (19) |
| C7A—C2A—C3A—C4A | −0.4 (3) | C7B—C2B—C3B—C4B | 0.0 (3) |
| C1A—C2A—C3A—C4A | −174.53 (19) | C1B—C2B—C3B—C4B | −175.04 (19) |
| C2A—C3A—C4A—C5A | 0.0 (3) | C2B—C3B—C4B—C5B | 1.2 (3) |
| C3A—C4A—C5A—C6A | 0.5 (3) | C3B—C4B—C5B—C6B | −1.0 (3) |
| C4A—C5A—C6A—C7A | −0.6 (3) | C4B—C5B—C6B—C7B | −0.5 (3) |
| C5A—C6A—C7A—C2A | 0.2 (3) | C5B—C6B—C7B—C2B | 1.6 (3) |
| C5A—C6A—C7A—C8A | 173.23 (19) | C5B—C6B—C7B—C8B | 176.15 (19) |
| C3A—C2A—C7A—C6A | 0.3 (3) | C3B—C2B—C7B—C6B | −1.4 (3) |
| C1A—C2A—C7A—C6A | 175.80 (16) | C1B—C2B—C7B—C6B | 174.71 (17) |
| C3A—C2A—C7A—C8A | −174.25 (16) | C3B—C2B—C7B—C8B | −177.13 (16) |
| C1A—C2A—C7A—C8A | 1.23 (19) | C1B—C2B—C7B—C8B | −1.0 (2) |
| C9A—N2A—C8A—N1A | 7.0 (3) | C9B—N2B—C8B—N1B | 9.5 (2) |
| C9A—N2A—C8A—C7A | −154.32 (18) | C9B—N2B—C8B—C7B | −154.26 (18) |
| C1A—N1A—C8A—N2A | −151.72 (17) | C1B—N1B—C8B—N2B | −155.48 (16) |
| B1A—N1A—C8A—N2A | 13.5 (3) | B1B—N1B—C8B—N2B | 10.1 (3) |
| C1A—N1A—C8A—C7A | 13.34 (19) | C1B—N1B—C8B—C7B | 11.7 (2) |
| B1A—N1A—C8A—C7A | 178.51 (15) | B1B—N1B—C8B—C7B | 177.36 (15) |
| C6A—C7A—C8A—N2A | −18.4 (3) | C6B—C7B—C8B—N2B | −15.3 (3) |
| C2A—C7A—C8A—N2A | 155.33 (18) | C2B—C7B—C8B—N2B | 159.74 (18) |
| C6A—C7A—C8A—N1A | 177.79 (18) | C6B—C7B—C8B—N1B | 178.87 (19) |
| C2A—C7A—C8A—N1A | −8.47 (19) | C2B—C7B—C8B—N1B | −6.09 (19) |
| C8A—N2A—C9A—N3A | −9.0 (3) | C8B—N2B—C9B—N3B | −6.3 (2) |
| C8A—N2A—C9A—C10A | 153.80 (19) | C8B—N2B—C9B—C10B | 157.78 (18) |
| C16A—N3A—C9A—N2A | 155.46 (17) | C16B—N3B—C9B—N2B | 157.76 (16) |
| B1A—N3A—C9A—N2A | −9.4 (3) | B1B—N3B—C9B—N2B | −16.9 (3) |
| C16A—N3A—C9A—C10A | −10.8 (2) | C16B—N3B—C9B—C10B | −10.0 (2) |
| B1A—N3A—C9A—C10A | −175.61 (16) | B1B—N3B—C9B—C10B | 175.33 (15) |
| N2A—C9A—C10A—C11A | 13.2 (3) | N2B—C9B—C10B—C11B | 14.0 (3) |
| N3A—C9A—C10A—C11A | 178.3 (2) | N3B—C9B—C10B—C11B | −179.86 (19) |
| N2A—C9A—C10A—C15A | −159.18 (19) | N2B—C9B—C10B—C15B | −160.80 (19) |
| N3A—C9A—C10A—C15A | 5.9 (2) | N3B—C9B—C10B—C15B | 5.31 (19) |
| C15A—C10A—C11A—C12A | −1.1 (3) | C15B—C10B—C11B—C12B | −1.2 (3) |
| C9A—C10A—C11A—C12A | −172.6 (2) | C9B—C10B—C11B—C12B | −175.47 (19) |
| C10A—C11A—C12A—C13A | 0.8 (3) | C10B—C11B—C12B—C13B | 0.7 (3) |
| C11A—C12A—C13A—C14A | 0.3 (3) | C11B—C12B—C13B—C14B | 0.6 (4) |
| C12A—C13A—C14A—C15A | −1.0 (3) | C12B—C13B—C14B—C15B | −1.4 (3) |
| C13A—C14A—C15A—C10A | 0.7 (3) | C13B—C14B—C15B—C10B | 0.8 (3) |
| C13A—C14A—C15A—C16A | 171.95 (19) | C13B—C14B—C15B—C16B | 175.0 (2) |
| C11A—C10A—C15A—C14A | 0.3 (3) | C11B—C10B—C15B—C14B | 0.5 (3) |
| C9A—C10A—C15A—C14A | 173.74 (17) | C9B—C10B—C15B—C14B | 175.99 (17) |
| C11A—C10A—C15A—C16A | −172.86 (17) | C11B—C10B—C15B—C16B | −174.97 (17) |
| C9A—C10A—C15A—C16A | 0.5 (2) | C9B—C10B—C15B—C16B | 0.5 (2) |
| C17A—N4A—C16A—N3A | 9.3 (3) | C17B—N4B—C16B—N3B | 6.9 (3) |
| C17A—N4A—C16A—C15A | −152.40 (19) | C17B—N4B—C16B—C15B | −158.25 (19) |
| C9A—N3A—C16A—N4A | −154.32 (17) | C9B—N3B—C16B—N4B | −158.29 (17) |
| B1A—N3A—C16A—N4A | 10.5 (3) | B1B—N3B—C16B—N4B | 16.4 (3) |
| C9A—N3A—C16A—C15A | 11.1 (2) | C9B—N3B—C16B—C15B | 10.3 (2) |
| B1A—N3A—C16A—C15A | 175.90 (16) | B1B—N3B—C16B—C15B | −175.01 (15) |
| C14A—C15A—C16A—N4A | −14.8 (3) | C14B—C15B—C16B—N4B | −13.9 (4) |
| C10A—C15A—C16A—N4A | 157.29 (19) | C10B—C15B—C16B—N4B | 160.87 (19) |
| C14A—C15A—C16A—N3A | −178.9 (2) | C14B—C15B—C16B—N3B | 179.1 (2) |
| C10A—C15A—C16A—N3A | −6.8 (2) | C10B—C15B—C16B—N3B | −6.1 (2) |
| C16A—N4A—C17A—N5A | −8.4 (3) | C16B—N4B—C17B—N5B | −9.5 (3) |
| C16A—N4A—C17A—C18A | 152.33 (18) | C16B—N4B—C17B—C18B | 154.72 (19) |
| C24A—N5A—C17A—N4A | 152.10 (17) | C24B—N5B—C17B—N4B | 155.44 (17) |
| B1A—N5A—C17A—N4A | −12.2 (3) | B1B—N5B—C17B—N4B | −10.7 (3) |
| C24A—N5A—C17A—C18A | −12.5 (2) | C24B—N5B—C17B—C18B | −12.2 (2) |
| B1A—N5A—C17A—C18A | −176.86 (16) | B1B—N5B—C17B—C18B | −178.41 (16) |
| N4A—C17A—C18A—C19A | 19.3 (3) | N4B—C17B—C18B—C19B | 16.7 (4) |
| N5A—C17A—C18A—C19A | −177.40 (19) | N5B—C17B—C18B—C19B | −177.1 (2) |
| N4A—C17A—C18A—C23A | −155.39 (19) | N4B—C17B—C18B—C23B | −158.9 (2) |
| N5A—C17A—C18A—C23A | 7.9 (2) | N5B—C17B—C18B—C23B | 7.3 (2) |
| C23A—C18A—C19A—C20A | −0.5 (3) | C23B—C18B—C19B—C20B | −1.8 (3) |
| C17A—C18A—C19A—C20A | −174.55 (19) | C17B—C18B—C19B—C20B | −176.9 (2) |
| C18A—C19A—C20A—C21A | 2.3 (3) | C18B—C19B—C20B—C21B | 1.6 (3) |
| C19A—C20A—C21A—C22A | −1.8 (3) | C19B—C20B—C21B—C22B | −0.2 (4) |
| C20A—C21A—C22A—C23A | −0.6 (3) | C20B—C21B—C22B—C23B | −1.0 (3) |
| C21A—C22A—C23A—C18A | 2.3 (3) | C21B—C22B—C23B—C18B | 0.8 (3) |
| C21A—C22A—C23A—C24A | 175.47 (19) | C21B—C22B—C23B—C24B | 177.4 (2) |
| C19A—C18A—C23A—C22A | −1.9 (3) | C19B—C18B—C23B—C22B | 0.6 (3) |
| C17A—C18A—C23A—C22A | 173.52 (17) | C17B—C18B—C23B—C22B | 176.85 (17) |
| C19A—C18A—C23A—C24A | −176.50 (17) | C19B—C18B—C23B—C24B | −176.74 (18) |
| C17A—C18A—C23A—C24A | −1.1 (2) | C17B—C18B—C23B—C24B | −0.5 (2) |
| C1A—N6A—C24A—N5A | 7.9 (3) | C1B—N6B—C24B—N5B | 8.5 (3) |
| C1A—N6A—C24A—C23A | −155.16 (18) | C1B—N6B—C24B—C23B | −155.83 (19) |
| C17A—N5A—C24A—N6A | −154.60 (17) | C17B—N5B—C24B—N6B | −155.70 (17) |
| B1A—N5A—C24A—N6A | 9.6 (3) | B1B—N5B—C24B—N6B | 10.4 (3) |
| C17A—N5A—C24A—C23A | 11.9 (2) | C17B—N5B—C24B—C23B | 11.9 (2) |
| B1A—N5A—C24A—C23A | 176.07 (16) | B1B—N5B—C24B—C23B | 178.02 (16) |
| C22A—C23A—C24A—N6A | −14.6 (3) | C22B—C23B—C24B—N6B | −17.1 (4) |
| C18A—C23A—C24A—N6A | 159.18 (18) | C18B—C23B—C24B—N6B | 159.83 (19) |
| C22A—C23A—C24A—N5A | −179.97 (19) | C22B—C23B—C24B—N5B | 176.5 (2) |
| C18A—C23A—C24A—N5A | −6.1 (2) | C18B—C23B—C24B—N5B | −6.5 (2) |
| B1A—S1A—C25A—C30A | −93.53 (17) | B1B—S1B—C25B—C30B | −84.01 (17) |
| B1A—S1A—C25A—C26A | 85.40 (17) | B1B—S1B—C25B—C26B | 96.28 (17) |
| C30A—C25A—C26A—F1A | −178.39 (17) | C30B—C25B—C26B—F1B | 179.89 (17) |
| S1A—C25A—C26A—F1A | 2.6 (3) | S1B—C25B—C26B—F1B | −0.4 (3) |
| C30A—C25A—C26A—C27A | 2.2 (3) | C30B—C25B—C26B—C27B | −0.1 (3) |
| S1A—C25A—C26A—C27A | −176.77 (16) | S1B—C25B—C26B—C27B | 179.64 (16) |
| F1A—C26A—C27A—F2A | 0.0 (3) | F1B—C26B—C27B—F2B | 1.0 (3) |
| C25A—C26A—C27A—F2A | 179.41 (18) | C25B—C26B—C27B—F2B | −179.01 (18) |
| F1A—C26A—C27A—C28A | 179.43 (19) | F1B—C26B—C27B—C28B | −179.61 (19) |
| C25A—C26A—C27A—C28A | −1.2 (3) | C25B—C26B—C27B—C28B | 0.4 (3) |
| F2A—C27A—C28A—F3A | −0.4 (3) | F2B—C27B—C28B—F3B | 0.1 (3) |
| C26A—C27A—C28A—F3A | −179.9 (2) | C26B—C27B—C28B—F3B | −179.34 (19) |
| F2A—C27A—C28A—C29A | 179.0 (2) | F2B—C27B—C28B—C29B | 179.0 (2) |
| C26A—C27A—C28A—C29A | −0.5 (3) | C26B—C27B—C28B—C29B | −0.4 (3) |
| F3A—C28A—C29A—F4A | 0.9 (3) | F3B—C28B—C29B—F4B | −0.1 (3) |
| C27A—C28A—C29A—F4A | −178.5 (2) | C27B—C28B—C29B—F4B | −179.1 (2) |
| F3A—C28A—C29A—C30A | −179.7 (2) | F3B—C28B—C29B—C30B | 179.10 (19) |
| C27A—C28A—C29A—C30A | 0.9 (3) | C27B—C28B—C29B—C30B | 0.2 (3) |
| F4A—C29A—C30A—F5A | −1.1 (3) | F4B—C29B—C30B—F5B | −1.2 (3) |
| C28A—C29A—C30A—F5A | 179.53 (19) | C28B—C29B—C30B—F5B | 179.53 (19) |
| F4A—C29A—C30A—C25A | 179.61 (18) | F4B—C29B—C30B—C25B | 179.37 (19) |
| C28A—C29A—C30A—C25A | 0.2 (3) | C28B—C29B—C30B—C25B | 0.1 (3) |
| C26A—C25A—C30A—F5A | 178.96 (17) | C26B—C25B—C30B—F5B | −179.54 (17) |
| S1A—C25A—C30A—F5A | −2.0 (3) | S1B—C25B—C30B—F5B | 0.7 (3) |
| C26A—C25A—C30A—C29A | −1.7 (3) | C26B—C25B—C30B—C29B | −0.2 (3) |
| S1A—C25A—C30A—C29A | 177.24 (16) | S1B—C25B—C30B—C29B | −179.89 (16) |
| C16A—N3A—B1A—N1A | −137.85 (16) | C9B—N3B—B1B—N1B | 31.7 (2) |
| C9A—N3A—B1A—N1A | 25.4 (2) | C16B—N3B—B1B—N1B | −142.52 (16) |
| C16A—N3A—B1A—N5A | −26.6 (2) | C9B—N3B—B1B—N5B | 142.72 (16) |
| C9A—N3A—B1A—N5A | 136.68 (16) | C16B—N3B—B1B—N5B | −31.5 (2) |
| C16A—N3A—B1A—S1A | 99.80 (18) | C9B—N3B—B1B—S1B | −91.46 (18) |
| C9A—N3A—B1A—S1A | −96.93 (18) | C16B—N3B—B1B—S1B | 94.28 (18) |
| C8A—N1A—B1A—N3A | −27.3 (2) | C1B—N1B—B1B—N3B | 135.81 (17) |
| C1A—N1A—B1A—N3A | 136.30 (16) | C8B—N1B—B1B—N3B | −28.3 (2) |
| C8A—N1A—B1A—N5A | −138.50 (16) | C1B—N1B—B1B—N5B | 25.0 (2) |
| C1A—N1A—B1A—N5A | 25.1 (2) | C8B—N1B—B1B—N5B | −139.04 (16) |
| C8A—N1A—B1A—S1A | 96.55 (17) | C1B—N1B—B1B—S1B | −101.90 (17) |
| C1A—N1A—B1A—S1A | −99.83 (17) | C8B—N1B—B1B—S1B | 94.02 (18) |
| C24A—N5A—B1A—N3A | −135.37 (17) | C17B—N5B—B1B—N3B | 28.8 (2) |
| C17A—N5A—B1A—N3A | 27.3 (2) | C24B—N5B—B1B—N3B | −136.01 (17) |
| C24A—N5A—B1A—N1A | −24.0 (2) | C17B—N5B—B1B—N1B | 139.91 (17) |
| C17A—N5A—B1A—N1A | 138.70 (16) | C24B—N5B—B1B—N1B | −24.9 (2) |
| C24A—N5A—B1A—S1A | 98.83 (18) | C17B—N5B—B1B—S1B | −94.60 (19) |
| C17A—N5A—B1A—S1A | −98.46 (18) | C24B—N5B—B1B—S1B | 100.57 (18) |
(4-Methylbenzenethiolato)(subphthalocyaninato)boron (d23112_a_tw_sq) top
Crystal data top
| C31H19BN6S | F(000) = 6432 |
| Mr = 518.39 | Dx = 1.372 Mg m−3 |
| Monoclinic, C2/c | Cu Kα radiation, λ = 1.54178 Å |
| a = 49.653 (4) Å | Cell parameters from 6283 reflections |
| b = 12.1268 (10) Å | θ = 3.5–62.5° |
| c = 27.559 (2) Å | µ = 1.41 mm−1 |
| β = 114.838 (4)° | T = 150 K |
| V = 15059 (2) Å3 | Plate, pink |
| Z = 24 | 0.28 × 0.27 × 0.02 mm |
Data collection top
| Bruker Kappa APEX-DUO CMOS PHOTON II diffractometer | 10107 reflections with I > 2σ(I) |
| Radiation source: Incoatec ImuS with multi-layer optics | Rint = 0.091 |
| φ and ω scans | θmax = 66.3°, θmin = 2.0° |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −58→58 |
| Tmin = 0.633, Tmax = 0.753 | k = −14→14 |
| 12819 measured reflections | l = −21→32 |
| 12819 independent reflections |
Refinement top
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.098 | w = 1/[σ2(Fo2) + (0.0341P)2 + 145.1404P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.242 | (Δ/σ)max = 0.001 |
| S = 1.09 | Δρmax = 0.89 e Å−3 |
| 12819 reflections | Δρmin = −0.57 e Å−3 |
| 1059 parameters | Extinction correction: SHELXL2019 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| 0 restraints | Extinction coefficient: 0.00058 (4) |
| Primary atom site location: structure-invariant direct methods |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refined as a 2-component twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| S1A | 0.59339 (3) | 0.51753 (12) | 0.73057 (6) | 0.0332 (4) | |
| N1A | 0.59808 (10) | 0.5166 (4) | 0.63321 (19) | 0.0319 (11) | |
| N2A | 0.56798 (11) | 0.3623 (4) | 0.5883 (2) | 0.0362 (12) | |
| N3A | 0.54799 (10) | 0.5100 (4) | 0.62041 (19) | 0.0340 (11) | |
| N4A | 0.52161 (10) | 0.6784 (4) | 0.60952 (19) | 0.0345 (11) | |
| N5A | 0.57430 (10) | 0.6766 (4) | 0.64365 (19) | 0.0308 (11) | |
| N6A | 0.61955 (10) | 0.6927 (4) | 0.63371 (19) | 0.0335 (11) | |
| C1A | 0.61884 (12) | 0.5823 (5) | 0.6276 (2) | 0.0334 (13) | |
| C2A | 0.63308 (13) | 0.5140 (5) | 0.6021 (2) | 0.0363 (14) | |
| C3A | 0.65616 (13) | 0.5368 (6) | 0.5868 (3) | 0.0401 (15) | |
| H3AA | 0.666057 | 0.605947 | 0.594543 | 0.048* | |
| C4A | 0.66399 (14) | 0.4552 (6) | 0.5603 (3) | 0.0452 (16) | |
| H4AA | 0.679585 | 0.468532 | 0.549612 | 0.054* | |
| C5A | 0.64946 (14) | 0.3538 (6) | 0.5487 (3) | 0.0446 (16) | |
| H5AA | 0.655837 | 0.298714 | 0.531338 | 0.053* | |
| C6A | 0.62604 (14) | 0.3308 (6) | 0.5618 (2) | 0.0413 (15) | |
| H6AA | 0.615838 | 0.262355 | 0.552509 | 0.050* | |
| C7A | 0.61790 (13) | 0.4118 (5) | 0.5892 (2) | 0.0349 (14) | |
| C8A | 0.59385 (13) | 0.4191 (5) | 0.6056 (2) | 0.0325 (13) | |
| C9A | 0.54495 (13) | 0.4124 (5) | 0.5934 (2) | 0.0338 (13) | |
| C10A | 0.51306 (13) | 0.3972 (5) | 0.5631 (2) | 0.0365 (14) | |
| C11A | 0.49668 (14) | 0.3119 (6) | 0.5302 (2) | 0.0403 (15) | |
| H11A | 0.506026 | 0.247966 | 0.524520 | 0.048* | |
| C12A | 0.46574 (14) | 0.3245 (6) | 0.5058 (3) | 0.0453 (16) | |
| H12A | 0.453893 | 0.266894 | 0.483772 | 0.054* | |
| C13A | 0.45193 (14) | 0.4187 (6) | 0.5129 (3) | 0.0466 (17) | |
| H13A | 0.430901 | 0.423987 | 0.495932 | 0.056* | |
| C14A | 0.46833 (13) | 0.5054 (6) | 0.5444 (3) | 0.0414 (15) | |
| H14A | 0.458900 | 0.570878 | 0.548139 | 0.050* | |
| C15A | 0.49906 (13) | 0.4934 (6) | 0.5703 (2) | 0.0362 (14) | |
| C16A | 0.52231 (12) | 0.5687 (5) | 0.6040 (2) | 0.0323 (13) | |
| C17A | 0.54772 (12) | 0.7320 (5) | 0.6269 (2) | 0.0317 (13) | |
| C18A | 0.55452 (13) | 0.8458 (5) | 0.6203 (2) | 0.0333 (13) | |
| C19A | 0.53729 (14) | 0.9420 (6) | 0.6065 (2) | 0.0402 (15) | |
| H19A | 0.517001 | 0.939765 | 0.600476 | 0.048* | |
| C20A | 0.55014 (16) | 1.0400 (6) | 0.6019 (3) | 0.0444 (16) | |
| H20A | 0.538811 | 1.106064 | 0.593581 | 0.053* | |
| C21A | 0.57980 (16) | 1.0422 (6) | 0.6095 (3) | 0.0468 (16) | |
| H21A | 0.588281 | 1.110399 | 0.606119 | 0.056* | |
| C22A | 0.59720 (14) | 0.9482 (5) | 0.6217 (2) | 0.0384 (14) | |
| H22A | 0.617209 | 0.950849 | 0.626024 | 0.046* | |
| C23A | 0.58454 (13) | 0.8503 (5) | 0.6274 (2) | 0.0344 (13) | |
| C24A | 0.59621 (12) | 0.7387 (5) | 0.6388 (2) | 0.0320 (13) | |
| C25A | 0.57037 (12) | 0.5904 (5) | 0.7551 (2) | 0.0327 (13) | |
| C26A | 0.55151 (14) | 0.5325 (6) | 0.7712 (3) | 0.0409 (15) | |
| H26A | 0.549561 | 0.454854 | 0.766458 | 0.049* | |
| C27A | 0.53520 (14) | 0.5895 (6) | 0.7946 (3) | 0.0423 (16) | |
| H27A | 0.522325 | 0.549187 | 0.805590 | 0.051* | |
| C28A | 0.53746 (13) | 0.7018 (6) | 0.8019 (2) | 0.0372 (14) | |
| C29A | 0.55642 (12) | 0.7579 (5) | 0.7854 (2) | 0.0342 (13) | |
| H29A | 0.558272 | 0.835583 | 0.789992 | 0.041* | |
| C30A | 0.57274 (12) | 0.7044 (5) | 0.7623 (2) | 0.0320 (13) | |
| H30A | 0.585579 | 0.745279 | 0.751451 | 0.038* | |
| C31A | 0.51886 (14) | 0.7624 (7) | 0.8245 (3) | 0.0503 (18) | |
| H31A | 0.522446 | 0.841826 | 0.824314 | 0.075* | |
| H31B | 0.524201 | 0.737849 | 0.861285 | 0.075* | |
| H31C | 0.497821 | 0.746979 | 0.802649 | 0.075* | |
| B1A | 0.57748 (14) | 0.5575 (6) | 0.6563 (3) | 0.0310 (14) | |
| S1B | 0.70480 (3) | 0.12941 (13) | 0.54527 (5) | 0.0330 (4) | |
| N1B | 0.75052 (9) | 0.1664 (4) | 0.64832 (18) | 0.0259 (10) | |
| N2B | 0.73408 (9) | 0.3260 (4) | 0.67907 (18) | 0.0285 (10) | |
| N3B | 0.70331 (9) | 0.1666 (4) | 0.64869 (18) | 0.0263 (10) | |
| N4B | 0.68356 (10) | −0.0029 (4) | 0.66323 (18) | 0.0282 (10) | |
| N5B | 0.72493 (9) | −0.0007 (4) | 0.64095 (18) | 0.0273 (10) | |
| N6B | 0.77646 (10) | −0.0037 (4) | 0.66115 (18) | 0.0293 (10) | |
| C1B | 0.77611 (12) | 0.1075 (5) | 0.6624 (2) | 0.0276 (12) | |
| C2B | 0.80016 (12) | 0.1853 (5) | 0.6884 (2) | 0.0288 (12) | |
| C3B | 0.83085 (12) | 0.1732 (5) | 0.7092 (2) | 0.0303 (12) | |
| H3BA | 0.839539 | 0.105418 | 0.705949 | 0.036* | |
| C4B | 0.84822 (12) | 0.2619 (5) | 0.7346 (2) | 0.0337 (13) | |
| H4BA | 0.869198 | 0.255873 | 0.748314 | 0.040* | |
| C5B | 0.83550 (12) | 0.3618 (5) | 0.7408 (2) | 0.0323 (13) | |
| H5BA | 0.848048 | 0.421961 | 0.758434 | 0.039* | |
| C6B | 0.80492 (12) | 0.3738 (5) | 0.7216 (2) | 0.0311 (13) | |
| H6BA | 0.796367 | 0.440026 | 0.727068 | 0.037* | |
| C7B | 0.78730 (11) | 0.2855 (5) | 0.6941 (2) | 0.0271 (12) | |
| C8B | 0.75513 (12) | 0.2692 (5) | 0.6715 (2) | 0.0275 (12) | |
| C9B | 0.70903 (12) | 0.2702 (5) | 0.6704 (2) | 0.0267 (12) | |
| C10B | 0.68695 (12) | 0.2891 (5) | 0.6915 (2) | 0.0287 (12) | |
| C11B | 0.68130 (12) | 0.3792 (5) | 0.7165 (2) | 0.0317 (13) | |
| H11B | 0.692027 | 0.446073 | 0.720578 | 0.038* | |
| C12B | 0.65958 (13) | 0.3696 (5) | 0.7354 (2) | 0.0366 (14) | |
| H12B | 0.654985 | 0.431143 | 0.751909 | 0.044* | |
| C13B | 0.64448 (12) | 0.2709 (5) | 0.7306 (2) | 0.0356 (14) | |
| H13B | 0.629667 | 0.266694 | 0.743884 | 0.043* | |
| C14B | 0.65024 (12) | 0.1797 (5) | 0.7074 (2) | 0.0302 (13) | |
| H14B | 0.640028 | 0.112341 | 0.705296 | 0.036* | |
| C15B | 0.67155 (11) | 0.1880 (5) | 0.6868 (2) | 0.0286 (12) | |
| C16B | 0.68418 (11) | 0.1081 (5) | 0.6630 (2) | 0.0274 (12) | |
| C17B | 0.70515 (12) | −0.0555 (5) | 0.6548 (2) | 0.0278 (12) | |
| C18B | 0.71713 (12) | −0.1672 (5) | 0.6689 (2) | 0.0336 (13) | |
| C19B | 0.70641 (14) | −0.2611 (5) | 0.6833 (2) | 0.0358 (14) | |
| H19B | 0.687557 | −0.261993 | 0.684404 | 0.043* | |
| C20B | 0.72429 (15) | −0.3530 (6) | 0.6958 (3) | 0.0478 (17) | |
| H20B | 0.717224 | −0.418854 | 0.705152 | 0.057* | |
| C21B | 0.75224 (15) | −0.3540 (5) | 0.6956 (3) | 0.0441 (16) | |
| H21B | 0.763789 | −0.419539 | 0.704640 | 0.053* | |
| C22B | 0.76322 (13) | −0.2598 (5) | 0.6821 (2) | 0.0370 (14) | |
| H22B | 0.782448 | −0.259470 | 0.682484 | 0.044* | |
| C23B | 0.74577 (13) | −0.1664 (5) | 0.6680 (2) | 0.0312 (13) | |
| C24B | 0.75077 (12) | −0.0554 (5) | 0.6532 (2) | 0.0300 (12) | |
| C25B | 0.67610 (12) | 0.0277 (5) | 0.5266 (2) | 0.0323 (13) | |
| C26B | 0.65046 (12) | 0.0452 (5) | 0.5346 (2) | 0.0354 (14) | |
| H26B | 0.647228 | 0.114717 | 0.547077 | 0.042* | |
| C27B | 0.62986 (13) | −0.0375 (6) | 0.5245 (2) | 0.0397 (15) | |
| H27B | 0.612757 | −0.023714 | 0.530755 | 0.048* | |
| C28B | 0.63306 (14) | −0.1393 (6) | 0.5056 (2) | 0.0414 (15) | |
| C29B | 0.65804 (15) | −0.1544 (6) | 0.4943 (3) | 0.0473 (17) | |
| H29B | 0.660582 | −0.222266 | 0.479532 | 0.057* | |
| C30B | 0.67888 (14) | −0.0714 (6) | 0.5044 (2) | 0.0412 (15) | |
| H30B | 0.695360 | −0.082835 | 0.495964 | 0.049* | |
| C31B | 0.61155 (16) | −0.2325 (6) | 0.4988 (3) | 0.0531 (19) | |
| H31D | 0.611549 | −0.250304 | 0.533455 | 0.080* | |
| H31E | 0.617600 | −0.297530 | 0.484722 | 0.080* | |
| H31F | 0.591564 | −0.209982 | 0.473728 | 0.080* | |
| B1B | 0.72051 (13) | 0.1155 (5) | 0.6211 (2) | 0.0263 (13) | |
| S1C | 0.59674 (3) | 0.00520 (14) | 0.75499 (6) | 0.0351 (4) | |
| N1C | 0.64464 (10) | −0.0089 (4) | 0.85662 (19) | 0.0343 (11) | |
| N2C | 0.66937 (12) | 0.1610 (5) | 0.8589 (2) | 0.0444 (13) | |
| N3C | 0.61870 (10) | 0.1582 (4) | 0.84376 (19) | 0.0350 (11) | |
| N4C | 0.57961 (12) | 0.1708 (5) | 0.8714 (2) | 0.0413 (13) | |
| N5C | 0.59878 (10) | −0.0031 (4) | 0.86186 (19) | 0.0329 (11) | |
| N6C | 0.63067 (11) | −0.1585 (4) | 0.89589 (19) | 0.0381 (12) | |
| C1C | 0.65042 (13) | −0.1077 (5) | 0.8820 (2) | 0.0366 (14) | |
| C2C | 0.68224 (13) | −0.1231 (6) | 0.9004 (2) | 0.0433 (17) | |
| C3C | 0.70084 (16) | −0.2118 (7) | 0.9261 (2) | 0.055 (2) | |
| H3C | 0.693213 | −0.277165 | 0.934668 | 0.066* | |
| C4C | 0.73082 (18) | −0.2007 (10) | 0.9385 (3) | 0.071 (3) | |
| H4CA | 0.743743 | −0.261659 | 0.952994 | 0.085* | |
| C5C | 0.74220 (17) | −0.1016 (10) | 0.9301 (3) | 0.076 (3) | |
| H5CA | 0.763031 | −0.095861 | 0.941152 | 0.091* | |
| C6C | 0.72503 (15) | −0.0121 (8) | 0.9068 (3) | 0.057 (2) | |
| H6CA | 0.733431 | 0.055046 | 0.901987 | 0.069* | |
| C7C | 0.69402 (13) | −0.0241 (7) | 0.8902 (2) | 0.0459 (18) | |
| C8C | 0.66960 (13) | 0.0509 (6) | 0.8652 (2) | 0.0394 (15) | |
| C9C | 0.64407 (15) | 0.2138 (6) | 0.8515 (2) | 0.0404 (15) | |
| C10C | 0.63896 (17) | 0.3269 (6) | 0.8620 (3) | 0.0507 (18) | |
| C11C | 0.6560 (2) | 0.4232 (7) | 0.8700 (3) | 0.066 (2) | |
| H11C | 0.674481 | 0.422407 | 0.867333 | 0.079* | |
| C12C | 0.6449 (3) | 0.5191 (8) | 0.8818 (3) | 0.079 (3) | |
| H12C | 0.655796 | 0.585541 | 0.885750 | 0.095* | |
| C13C | 0.6183 (3) | 0.5225 (7) | 0.8882 (3) | 0.079 (3) | |
| H13C | 0.611761 | 0.589764 | 0.897216 | 0.094* | |
| C14C | 0.6016 (2) | 0.4263 (6) | 0.8813 (3) | 0.060 (2) | |
| H14C | 0.583765 | 0.426662 | 0.886015 | 0.072* | |
| C15C | 0.61181 (17) | 0.3300 (6) | 0.8672 (3) | 0.0492 (17) | |
| C16C | 0.60011 (14) | 0.2183 (6) | 0.8584 (2) | 0.0405 (15) | |
| C17C | 0.58067 (12) | 0.0604 (6) | 0.8761 (2) | 0.0355 (14) | |
| C18C | 0.57047 (13) | −0.0113 (6) | 0.9071 (2) | 0.0382 (15) | |
| C19C | 0.55125 (14) | 0.0084 (7) | 0.9316 (3) | 0.0495 (18) | |
| H19C | 0.540768 | 0.076079 | 0.926546 | 0.059* | |
| C20C | 0.54811 (14) | −0.0745 (8) | 0.9634 (3) | 0.054 (2) | |
| H20C | 0.535243 | −0.063491 | 0.980550 | 0.064* | |
| C21C | 0.56364 (16) | −0.1745 (7) | 0.9708 (3) | 0.0526 (19) | |
| H21C | 0.560742 | −0.230226 | 0.992365 | 0.063* | |
| C22C | 0.58285 (15) | −0.1937 (6) | 0.9477 (2) | 0.0454 (16) | |
| H22C | 0.593796 | −0.260483 | 0.953975 | 0.055* | |
| C23C | 0.58581 (13) | −0.1113 (6) | 0.9145 (2) | 0.0371 (14) | |
| C24C | 0.60596 (13) | −0.1025 (5) | 0.8889 (2) | 0.0332 (13) | |
| C25C | 0.56426 (12) | 0.0896 (5) | 0.7315 (2) | 0.0308 (13) | |
| C26C | 0.56611 (13) | 0.2000 (5) | 0.7208 (3) | 0.0379 (14) | |
| H26C | 0.584909 | 0.231148 | 0.727599 | 0.045* | |
| C27C | 0.54095 (13) | 0.2661 (6) | 0.7002 (3) | 0.0402 (15) | |
| H27C | 0.542897 | 0.341742 | 0.693317 | 0.048* | |
| C28C | 0.51321 (13) | 0.2243 (5) | 0.6896 (2) | 0.0353 (14) | |
| C29C | 0.51136 (13) | 0.1125 (5) | 0.6996 (3) | 0.0388 (15) | |
| H29C | 0.492510 | 0.080992 | 0.692196 | 0.047* | |
| C30C | 0.53641 (13) | 0.0463 (5) | 0.7202 (2) | 0.0356 (14) | |
| H30C | 0.534470 | −0.029607 | 0.726607 | 0.043* | |
| C31C | 0.48627 (15) | 0.2975 (6) | 0.6687 (3) | 0.0513 (18) | |
| H31I | 0.492169 | 0.372800 | 0.664658 | 0.077* | |
| H31J | 0.477036 | 0.297331 | 0.693911 | 0.077* | |
| H31G | 0.472036 | 0.269956 | 0.633913 | 0.077* | |
| B1C | 0.61421 (14) | 0.0393 (6) | 0.8298 (3) | 0.0312 (14) |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1A | 0.0307 (7) | 0.0330 (8) | 0.0379 (8) | 0.0026 (6) | 0.0165 (6) | 0.0009 (6) |
| N1A | 0.032 (2) | 0.027 (3) | 0.039 (3) | −0.001 (2) | 0.017 (2) | −0.006 (2) |
| N2A | 0.035 (3) | 0.031 (3) | 0.045 (3) | 0.003 (2) | 0.020 (2) | 0.000 (2) |
| N3A | 0.029 (2) | 0.036 (3) | 0.040 (3) | 0.002 (2) | 0.017 (2) | −0.003 (2) |
| N4A | 0.031 (3) | 0.037 (3) | 0.037 (3) | −0.001 (2) | 0.017 (2) | −0.005 (2) |
| N5A | 0.029 (2) | 0.029 (3) | 0.036 (3) | 0.004 (2) | 0.015 (2) | −0.004 (2) |
| N6A | 0.032 (3) | 0.037 (3) | 0.032 (3) | 0.001 (2) | 0.014 (2) | 0.000 (2) |
| C1A | 0.026 (3) | 0.040 (4) | 0.031 (3) | 0.000 (3) | 0.010 (2) | −0.003 (3) |
| C2A | 0.031 (3) | 0.043 (4) | 0.033 (3) | 0.006 (3) | 0.012 (3) | 0.000 (3) |
| C3A | 0.032 (3) | 0.046 (4) | 0.046 (4) | 0.004 (3) | 0.021 (3) | 0.000 (3) |
| C4A | 0.039 (4) | 0.051 (4) | 0.053 (4) | 0.010 (3) | 0.027 (3) | −0.002 (3) |
| C5A | 0.044 (4) | 0.044 (4) | 0.050 (4) | 0.017 (3) | 0.024 (3) | −0.002 (3) |
| C6A | 0.043 (4) | 0.040 (4) | 0.042 (3) | 0.014 (3) | 0.019 (3) | 0.000 (3) |
| C7A | 0.033 (3) | 0.036 (4) | 0.038 (3) | 0.007 (3) | 0.017 (3) | 0.002 (3) |
| C8A | 0.033 (3) | 0.028 (3) | 0.034 (3) | 0.003 (3) | 0.012 (2) | −0.001 (2) |
| C9A | 0.032 (3) | 0.029 (3) | 0.042 (3) | −0.001 (3) | 0.018 (3) | −0.001 (3) |
| C10A | 0.033 (3) | 0.037 (4) | 0.041 (3) | −0.002 (3) | 0.017 (3) | −0.001 (3) |
| C11A | 0.042 (4) | 0.039 (4) | 0.041 (3) | −0.007 (3) | 0.019 (3) | −0.002 (3) |
| C12A | 0.036 (3) | 0.042 (4) | 0.052 (4) | −0.010 (3) | 0.013 (3) | 0.000 (3) |
| C13A | 0.029 (3) | 0.059 (5) | 0.048 (4) | −0.009 (3) | 0.013 (3) | 0.000 (3) |
| C14A | 0.034 (3) | 0.041 (4) | 0.050 (4) | 0.002 (3) | 0.019 (3) | 0.000 (3) |
| C15A | 0.030 (3) | 0.043 (4) | 0.039 (3) | 0.003 (3) | 0.017 (3) | 0.000 (3) |
| C16A | 0.030 (3) | 0.031 (3) | 0.041 (3) | 0.004 (3) | 0.020 (3) | 0.001 (3) |
| C17A | 0.030 (3) | 0.030 (3) | 0.037 (3) | 0.006 (3) | 0.017 (3) | −0.001 (3) |
| C18A | 0.039 (3) | 0.028 (3) | 0.033 (3) | 0.005 (3) | 0.015 (3) | −0.002 (2) |
| C19A | 0.042 (3) | 0.040 (4) | 0.036 (3) | 0.009 (3) | 0.013 (3) | −0.005 (3) |
| C20A | 0.058 (4) | 0.033 (4) | 0.039 (3) | 0.012 (3) | 0.018 (3) | 0.003 (3) |
| C21A | 0.056 (4) | 0.041 (4) | 0.044 (4) | −0.002 (3) | 0.023 (3) | 0.001 (3) |
| C22A | 0.043 (3) | 0.043 (4) | 0.031 (3) | 0.000 (3) | 0.017 (3) | −0.002 (3) |
| C23A | 0.040 (3) | 0.035 (4) | 0.031 (3) | 0.002 (3) | 0.018 (3) | −0.005 (2) |
| C24A | 0.029 (3) | 0.039 (4) | 0.030 (3) | −0.003 (3) | 0.015 (2) | −0.005 (2) |
| C25A | 0.029 (3) | 0.035 (3) | 0.035 (3) | 0.000 (3) | 0.014 (2) | 0.001 (3) |
| C26A | 0.038 (3) | 0.037 (4) | 0.050 (4) | −0.009 (3) | 0.021 (3) | 0.002 (3) |
| C27A | 0.037 (3) | 0.051 (4) | 0.050 (4) | −0.004 (3) | 0.030 (3) | 0.004 (3) |
| C28A | 0.031 (3) | 0.049 (4) | 0.035 (3) | 0.001 (3) | 0.017 (3) | 0.000 (3) |
| C29A | 0.028 (3) | 0.039 (4) | 0.035 (3) | 0.001 (3) | 0.013 (3) | −0.004 (3) |
| C30A | 0.031 (3) | 0.029 (3) | 0.038 (3) | −0.003 (2) | 0.016 (3) | −0.002 (2) |
| C31A | 0.037 (4) | 0.069 (5) | 0.054 (4) | 0.000 (3) | 0.027 (3) | −0.006 (4) |
| B1A | 0.029 (3) | 0.029 (4) | 0.036 (3) | 0.002 (3) | 0.015 (3) | −0.001 (3) |
| S1B | 0.0310 (7) | 0.0384 (9) | 0.0311 (7) | −0.0035 (6) | 0.0144 (6) | 0.0028 (6) |
| N1B | 0.022 (2) | 0.027 (3) | 0.032 (2) | −0.0017 (19) | 0.0153 (19) | 0.0033 (19) |
| N2B | 0.022 (2) | 0.031 (3) | 0.035 (3) | 0.001 (2) | 0.014 (2) | 0.003 (2) |
| N3B | 0.023 (2) | 0.026 (3) | 0.034 (2) | −0.0008 (19) | 0.0153 (19) | 0.0023 (19) |
| N4B | 0.026 (2) | 0.027 (3) | 0.034 (2) | −0.006 (2) | 0.015 (2) | −0.004 (2) |
| N5B | 0.025 (2) | 0.027 (3) | 0.034 (2) | 0.000 (2) | 0.016 (2) | 0.002 (2) |
| N6B | 0.026 (2) | 0.029 (3) | 0.034 (2) | −0.003 (2) | 0.014 (2) | −0.001 (2) |
| C1B | 0.030 (3) | 0.021 (3) | 0.037 (3) | −0.001 (2) | 0.018 (2) | 0.002 (2) |
| C2B | 0.026 (3) | 0.033 (3) | 0.032 (3) | −0.003 (2) | 0.017 (2) | 0.001 (2) |
| C3B | 0.025 (3) | 0.031 (3) | 0.036 (3) | 0.004 (2) | 0.014 (2) | 0.004 (2) |
| C4B | 0.025 (3) | 0.040 (4) | 0.037 (3) | −0.004 (3) | 0.015 (2) | 0.002 (3) |
| C5B | 0.027 (3) | 0.031 (3) | 0.040 (3) | −0.007 (2) | 0.014 (2) | −0.005 (3) |
| C6B | 0.030 (3) | 0.033 (3) | 0.035 (3) | 0.001 (3) | 0.018 (2) | 0.002 (3) |
| C7B | 0.022 (3) | 0.030 (3) | 0.035 (3) | 0.000 (2) | 0.017 (2) | 0.001 (2) |
| C8B | 0.025 (3) | 0.027 (3) | 0.034 (3) | 0.003 (2) | 0.017 (2) | 0.006 (2) |
| C9B | 0.027 (3) | 0.027 (3) | 0.029 (3) | −0.004 (2) | 0.015 (2) | 0.001 (2) |
| C10B | 0.024 (3) | 0.032 (3) | 0.033 (3) | 0.003 (2) | 0.015 (2) | 0.002 (2) |
| C11B | 0.027 (3) | 0.030 (3) | 0.039 (3) | −0.001 (2) | 0.014 (2) | 0.002 (3) |
| C12B | 0.034 (3) | 0.039 (4) | 0.043 (3) | 0.000 (3) | 0.023 (3) | −0.003 (3) |
| C13B | 0.027 (3) | 0.039 (4) | 0.044 (3) | 0.000 (3) | 0.018 (3) | 0.003 (3) |
| C14B | 0.026 (3) | 0.028 (3) | 0.041 (3) | 0.003 (2) | 0.018 (2) | 0.005 (2) |
| C15B | 0.019 (3) | 0.038 (3) | 0.029 (3) | 0.004 (2) | 0.010 (2) | 0.004 (2) |
| C16B | 0.022 (3) | 0.028 (3) | 0.032 (3) | −0.003 (2) | 0.011 (2) | 0.001 (2) |
| C17B | 0.026 (3) | 0.026 (3) | 0.032 (3) | −0.007 (2) | 0.013 (2) | −0.003 (2) |
| C18B | 0.030 (3) | 0.031 (3) | 0.040 (3) | −0.004 (3) | 0.015 (3) | −0.007 (3) |
| C19B | 0.038 (3) | 0.028 (3) | 0.045 (3) | −0.008 (3) | 0.021 (3) | −0.004 (3) |
| C20B | 0.053 (4) | 0.030 (4) | 0.066 (5) | −0.001 (3) | 0.031 (4) | 0.007 (3) |
| C21B | 0.046 (4) | 0.021 (3) | 0.068 (4) | 0.005 (3) | 0.027 (3) | 0.003 (3) |
| C22B | 0.033 (3) | 0.033 (4) | 0.045 (4) | 0.001 (3) | 0.016 (3) | −0.002 (3) |
| C23B | 0.033 (3) | 0.027 (3) | 0.037 (3) | 0.000 (2) | 0.018 (3) | −0.002 (2) |
| C24B | 0.028 (3) | 0.029 (3) | 0.036 (3) | 0.000 (2) | 0.016 (2) | −0.002 (2) |
| C25B | 0.032 (3) | 0.039 (4) | 0.026 (3) | 0.001 (3) | 0.012 (2) | 0.001 (2) |
| C26B | 0.029 (3) | 0.039 (4) | 0.037 (3) | 0.004 (3) | 0.013 (3) | −0.001 (3) |
| C27B | 0.026 (3) | 0.051 (4) | 0.040 (3) | −0.001 (3) | 0.012 (3) | 0.004 (3) |
| C28B | 0.039 (3) | 0.047 (4) | 0.035 (3) | −0.007 (3) | 0.013 (3) | 0.006 (3) |
| C29B | 0.051 (4) | 0.041 (4) | 0.050 (4) | −0.006 (3) | 0.022 (3) | −0.012 (3) |
| C30B | 0.038 (3) | 0.047 (4) | 0.041 (3) | 0.000 (3) | 0.018 (3) | −0.006 (3) |
| C31B | 0.055 (4) | 0.057 (5) | 0.047 (4) | −0.018 (4) | 0.021 (3) | 0.002 (3) |
| B1B | 0.023 (3) | 0.026 (3) | 0.031 (3) | −0.004 (3) | 0.012 (3) | −0.002 (3) |
| S1C | 0.0300 (7) | 0.0436 (9) | 0.0328 (7) | 0.0036 (6) | 0.0142 (6) | 0.0001 (6) |
| N1C | 0.027 (2) | 0.043 (3) | 0.036 (3) | 0.004 (2) | 0.016 (2) | 0.003 (2) |
| N2C | 0.041 (3) | 0.053 (4) | 0.044 (3) | −0.007 (3) | 0.022 (3) | −0.003 (3) |
| N3C | 0.032 (3) | 0.036 (3) | 0.039 (3) | 0.001 (2) | 0.016 (2) | 0.000 (2) |
| N4C | 0.040 (3) | 0.047 (4) | 0.035 (3) | 0.011 (3) | 0.015 (2) | 0.004 (2) |
| N5C | 0.029 (2) | 0.040 (3) | 0.032 (3) | 0.003 (2) | 0.015 (2) | 0.002 (2) |
| N6C | 0.040 (3) | 0.043 (3) | 0.031 (3) | 0.004 (2) | 0.014 (2) | −0.003 (2) |
| C1C | 0.034 (3) | 0.044 (4) | 0.032 (3) | 0.004 (3) | 0.014 (3) | −0.005 (3) |
| C2C | 0.032 (3) | 0.066 (5) | 0.026 (3) | 0.019 (3) | 0.007 (3) | −0.008 (3) |
| C3C | 0.050 (4) | 0.085 (6) | 0.028 (3) | 0.032 (4) | 0.013 (3) | −0.006 (3) |
| C4C | 0.053 (5) | 0.121 (9) | 0.033 (4) | 0.050 (5) | 0.012 (3) | −0.006 (5) |
| C5C | 0.036 (4) | 0.134 (10) | 0.051 (5) | 0.026 (5) | 0.013 (4) | −0.016 (5) |
| C6C | 0.034 (4) | 0.096 (7) | 0.046 (4) | 0.006 (4) | 0.021 (3) | −0.015 (4) |
| C7C | 0.024 (3) | 0.081 (6) | 0.032 (3) | 0.003 (3) | 0.012 (3) | −0.011 (3) |
| C8C | 0.034 (3) | 0.057 (5) | 0.034 (3) | −0.001 (3) | 0.020 (3) | −0.008 (3) |
| C9C | 0.050 (4) | 0.042 (4) | 0.036 (3) | −0.009 (3) | 0.024 (3) | 0.000 (3) |
| C10C | 0.067 (5) | 0.042 (4) | 0.042 (4) | −0.012 (4) | 0.022 (3) | 0.001 (3) |
| C11C | 0.094 (6) | 0.051 (5) | 0.060 (5) | −0.019 (5) | 0.040 (5) | 0.002 (4) |
| C12C | 0.141 (9) | 0.047 (5) | 0.061 (5) | −0.029 (6) | 0.053 (6) | −0.008 (4) |
| C13C | 0.140 (9) | 0.038 (5) | 0.058 (5) | 0.012 (5) | 0.042 (6) | 0.003 (4) |
| C14C | 0.089 (6) | 0.041 (5) | 0.046 (4) | 0.014 (4) | 0.025 (4) | 0.005 (3) |
| C15C | 0.064 (5) | 0.044 (4) | 0.041 (4) | 0.015 (4) | 0.024 (3) | 0.007 (3) |
| C16C | 0.043 (4) | 0.042 (4) | 0.035 (3) | 0.013 (3) | 0.014 (3) | 0.004 (3) |
| C17C | 0.028 (3) | 0.048 (4) | 0.029 (3) | 0.005 (3) | 0.011 (2) | −0.004 (3) |
| C18C | 0.028 (3) | 0.055 (4) | 0.033 (3) | 0.001 (3) | 0.015 (3) | 0.001 (3) |
| C19C | 0.031 (3) | 0.081 (6) | 0.039 (3) | −0.001 (3) | 0.017 (3) | −0.003 (4) |
| C20C | 0.031 (3) | 0.099 (7) | 0.036 (3) | −0.014 (4) | 0.019 (3) | −0.002 (4) |
| C21C | 0.047 (4) | 0.074 (6) | 0.035 (3) | −0.017 (4) | 0.016 (3) | 0.004 (3) |
| C22C | 0.044 (4) | 0.053 (4) | 0.036 (3) | −0.009 (3) | 0.013 (3) | 0.005 (3) |
| C23C | 0.034 (3) | 0.050 (4) | 0.028 (3) | −0.006 (3) | 0.014 (3) | −0.001 (3) |
| C24C | 0.034 (3) | 0.033 (3) | 0.031 (3) | 0.001 (3) | 0.013 (3) | 0.001 (2) |
| C25C | 0.027 (3) | 0.039 (4) | 0.029 (3) | −0.002 (3) | 0.015 (2) | −0.002 (2) |
| C26C | 0.026 (3) | 0.039 (4) | 0.048 (4) | −0.006 (3) | 0.014 (3) | 0.005 (3) |
| C27C | 0.034 (3) | 0.038 (4) | 0.048 (4) | −0.005 (3) | 0.017 (3) | 0.000 (3) |
| C28C | 0.033 (3) | 0.040 (4) | 0.034 (3) | 0.003 (3) | 0.016 (3) | 0.002 (3) |
| C29C | 0.030 (3) | 0.040 (4) | 0.047 (4) | −0.006 (3) | 0.017 (3) | 0.002 (3) |
| C30C | 0.036 (3) | 0.032 (3) | 0.040 (3) | −0.005 (3) | 0.017 (3) | 0.004 (3) |
| C31C | 0.043 (4) | 0.049 (5) | 0.065 (5) | 0.002 (3) | 0.025 (4) | 0.006 (4) |
| B1C | 0.032 (3) | 0.030 (4) | 0.033 (3) | 0.003 (3) | 0.015 (3) | 0.004 (3) |
Geometric parameters (Å, º) top
| S1A—C25A | 1.786 (6) | C12B—C13B | 1.388 (9) |
| S1A—B1A | 1.922 (7) | C12B—H12B | 0.9500 |
| N1A—C1A | 1.363 (7) | C13B—C14B | 1.368 (8) |
| N1A—C8A | 1.374 (7) | C13B—H13B | 0.9500 |
| N1A—B1A | 1.497 (8) | C14B—C15B | 1.399 (7) |
| N2A—C9A | 1.354 (7) | C14B—H14B | 0.9500 |
| N2A—C8A | 1.355 (8) | C15B—C16B | 1.452 (8) |
| N3A—C16A | 1.361 (7) | C17B—C18B | 1.465 (8) |
| N3A—C9A | 1.372 (8) | C18B—C19B | 1.383 (8) |
| N3A—B1A | 1.495 (8) | C18B—C23B | 1.432 (8) |
| N4A—C16A | 1.341 (8) | C19B—C20B | 1.376 (9) |
| N4A—C17A | 1.346 (7) | C19B—H19B | 0.9500 |
| N5A—C24A | 1.375 (7) | C20B—C21B | 1.391 (9) |
| N5A—C17A | 1.376 (7) | C20B—H20B | 0.9500 |
| N5A—B1A | 1.479 (8) | C21B—C22B | 1.382 (9) |
| N6A—C24A | 1.346 (7) | C21B—H21B | 0.9500 |
| N6A—C1A | 1.348 (8) | C22B—C23B | 1.379 (8) |
| C1A—C2A | 1.448 (8) | C22B—H22B | 0.9500 |
| C2A—C3A | 1.404 (8) | C23B—C24B | 1.458 (8) |
| C2A—C7A | 1.416 (9) | C25B—C30B | 1.381 (9) |
| C3A—C4A | 1.380 (9) | C25B—C26B | 1.396 (8) |
| C3A—H3AA | 0.9500 | C26B—C27B | 1.375 (9) |
| C4A—C5A | 1.394 (10) | C26B—H26B | 0.9500 |
| C4A—H4AA | 0.9500 | C27B—C28B | 1.375 (10) |
| C5A—C6A | 1.383 (9) | C27B—H27B | 0.9500 |
| C5A—H5AA | 0.9500 | C28B—C29B | 1.412 (9) |
| C6A—C7A | 1.397 (9) | C28B—C31B | 1.511 (9) |
| C6A—H6AA | 0.9500 | C29B—C30B | 1.385 (9) |
| C7A—C8A | 1.447 (8) | C29B—H29B | 0.9500 |
| C9A—C10A | 1.459 (8) | C30B—H30B | 0.9500 |
| C10A—C11A | 1.390 (9) | C31B—H31D | 0.9800 |
| C10A—C15A | 1.414 (9) | C31B—H31E | 0.9800 |
| C11A—C12A | 1.403 (9) | C31B—H31F | 0.9800 |
| C11A—H11A | 0.9500 | S1C—C25C | 1.786 (6) |
| C12A—C13A | 1.388 (10) | S1C—B1C | 1.915 (7) |
| C12A—H12A | 0.9500 | N1C—C1C | 1.357 (8) |
| C13A—C14A | 1.388 (9) | N1C—C8C | 1.368 (8) |
| C13A—H13A | 0.9500 | N1C—B1C | 1.494 (8) |
| C14A—C15A | 1.394 (8) | N2C—C8C | 1.345 (9) |
| C14A—H14A | 0.9500 | N2C—C9C | 1.347 (8) |
| C15A—C16A | 1.459 (9) | N3C—C16C | 1.364 (8) |
| C17A—C18A | 1.450 (9) | N3C—C9C | 1.364 (8) |
| C18A—C19A | 1.401 (9) | N3C—B1C | 1.486 (9) |
| C18A—C23A | 1.421 (8) | N4C—C16C | 1.342 (8) |
| C19A—C20A | 1.379 (10) | N4C—C17C | 1.344 (8) |
| C19A—H19A | 0.9500 | N5C—C17C | 1.361 (7) |
| C20A—C21A | 1.399 (10) | N5C—C24C | 1.383 (8) |
| C20A—H20A | 0.9500 | N5C—B1C | 1.484 (8) |
| C21A—C22A | 1.384 (9) | N6C—C1C | 1.343 (8) |
| C21A—H21A | 0.9500 | N6C—C24C | 1.344 (8) |
| C22A—C23A | 1.383 (9) | C1C—C2C | 1.454 (8) |
| C22A—H22A | 0.9500 | C2C—C3C | 1.400 (10) |
| C23A—C24A | 1.453 (9) | C2C—C7C | 1.415 (11) |
| C25A—C26A | 1.384 (8) | C3C—C4C | 1.387 (11) |
| C25A—C30A | 1.395 (8) | C3C—H3C | 0.9500 |
| C26A—C27A | 1.410 (9) | C4C—C5C | 1.388 (14) |
| C26A—H26A | 0.9500 | C4C—H4CA | 0.9500 |
| C27A—C28A | 1.374 (9) | C5C—C6C | 1.362 (13) |
| C27A—H27A | 0.9500 | C5C—H5CA | 0.9500 |
| C28A—C29A | 1.385 (8) | C6C—C7C | 1.417 (9) |
| C28A—C31A | 1.505 (8) | C6C—H6CA | 0.9500 |
| C29A—C30A | 1.384 (8) | C7C—C8C | 1.439 (10) |
| C29A—H29A | 0.9500 | C9C—C10C | 1.446 (10) |
| C30A—H30A | 0.9500 | C10C—C11C | 1.404 (11) |
| C31A—H31A | 0.9800 | C10C—C15C | 1.414 (10) |
| C31A—H31B | 0.9800 | C11C—C12C | 1.382 (13) |
| C31A—H31C | 0.9800 | C11C—H11C | 0.9500 |
| S1B—C25B | 1.789 (6) | C12C—C13C | 1.405 (14) |
| S1B—B1B | 1.907 (6) | C12C—H12C | 0.9500 |
| N1B—C1B | 1.364 (7) | C13C—C14C | 1.397 (13) |
| N1B—C8B | 1.376 (7) | C13C—H13C | 0.9500 |
| N1B—B1B | 1.491 (7) | C14C—C15C | 1.390 (10) |
| N2B—C8B | 1.338 (7) | C14C—H14C | 0.9500 |
| N2B—C9B | 1.346 (7) | C15C—C16C | 1.454 (10) |
| N3B—C16B | 1.369 (7) | C17C—C18C | 1.451 (9) |
| N3B—C9B | 1.370 (7) | C18C—C23C | 1.401 (9) |
| N3B—B1B | 1.495 (7) | C18C—C19C | 1.401 (8) |
| N4B—C16B | 1.345 (7) | C19C—C20C | 1.385 (11) |
| N4B—C17B | 1.349 (7) | C19C—H19C | 0.9500 |
| N5B—C24B | 1.355 (7) | C20C—C21C | 1.405 (11) |
| N5B—C17B | 1.366 (7) | C20C—H20C | 0.9500 |
| N5B—B1B | 1.494 (8) | C21C—C22C | 1.371 (10) |
| N6B—C1B | 1.349 (7) | C21C—H21C | 0.9500 |
| N6B—C24B | 1.354 (7) | C22C—C23C | 1.403 (9) |
| C1B—C2B | 1.453 (8) | C22C—H22C | 0.9500 |
| C2B—C3B | 1.392 (7) | C23C—C24C | 1.451 (8) |
| C2B—C7B | 1.412 (8) | C25C—C26C | 1.383 (9) |
| C3B—C4B | 1.373 (8) | C25C—C30C | 1.386 (8) |
| C3B—H3BA | 0.9500 | C26C—C27C | 1.389 (9) |
| C4B—C5B | 1.409 (9) | C26C—H26C | 0.9500 |
| C4B—H4BA | 0.9500 | C27C—C28C | 1.379 (8) |
| C5B—C6B | 1.390 (8) | C27C—H27C | 0.9500 |
| C5B—H5BA | 0.9500 | C28C—C29C | 1.394 (9) |
| C6B—C7B | 1.389 (8) | C28C—C31C | 1.504 (9) |
| C6B—H6BA | 0.9500 | C29C—C30C | 1.386 (9) |
| C7B—C8B | 1.464 (7) | C29C—H29C | 0.9500 |
| C9B—C10B | 1.458 (7) | C30C—H30C | 0.9500 |
| C10B—C11B | 1.382 (8) | C31C—H31I | 0.9800 |
| C10B—C15B | 1.422 (8) | C31C—H31J | 0.9800 |
| C11B—C12B | 1.387 (8) | C31C—H31G | 0.9800 |
| C11B—H11B | 0.9500 | ||
| C25A—S1A—B1A | 103.7 (3) | N4B—C16B—N3B | 122.7 (5) |
| C1A—N1A—C8A | 112.8 (5) | N4B—C16B—C15B | 130.5 (5) |
| C1A—N1A—B1A | 122.6 (5) | N3B—C16B—C15B | 105.5 (5) |
| C8A—N1A—B1A | 123.2 (5) | N4B—C17B—N5B | 122.3 (5) |
| C9A—N2A—C8A | 117.0 (5) | N4B—C17B—C18B | 131.0 (5) |
| C16A—N3A—C9A | 113.4 (5) | N5B—C17B—C18B | 105.4 (5) |
| C16A—N3A—B1A | 122.6 (5) | C19B—C18B—C23B | 121.0 (6) |
| C9A—N3A—B1A | 123.0 (5) | C19B—C18B—C17B | 132.4 (5) |
| C16A—N4A—C17A | 116.9 (5) | C23B—C18B—C17B | 106.6 (5) |
| C24A—N5A—C17A | 112.7 (5) | C20B—C19B—C18B | 117.0 (6) |
| C24A—N5A—B1A | 123.2 (5) | C20B—C19B—H19B | 121.5 |
| C17A—N5A—B1A | 123.3 (5) | C18B—C19B—H19B | 121.5 |
| C24A—N6A—C1A | 116.5 (5) | C19B—C20B—C21B | 123.1 (6) |
| N6A—C1A—N1A | 123.2 (5) | C19B—C20B—H20B | 118.5 |
| N6A—C1A—C2A | 129.5 (6) | C21B—C20B—H20B | 118.5 |
| N1A—C1A—C2A | 105.5 (5) | C22B—C21B—C20B | 120.1 (6) |
| C3A—C2A—C7A | 120.8 (6) | C22B—C21B—H21B | 119.9 |
| C3A—C2A—C1A | 131.3 (6) | C20B—C21B—H21B | 119.9 |
| C7A—C2A—C1A | 107.8 (5) | C23B—C22B—C21B | 118.8 (6) |
| C4A—C3A—C2A | 117.7 (6) | C23B—C22B—H22B | 120.6 |
| C4A—C3A—H3AA | 121.1 | C21B—C22B—H22B | 120.6 |
| C2A—C3A—H3AA | 121.1 | C22B—C23B—C18B | 120.1 (6) |
| C3A—C4A—C5A | 121.3 (6) | C22B—C23B—C24B | 132.6 (5) |
| C3A—C4A—H4AA | 119.4 | C18B—C23B—C24B | 107.3 (5) |
| C5A—C4A—H4AA | 119.4 | N6B—C24B—N5B | 122.8 (5) |
| C6A—C5A—C4A | 122.0 (6) | N6B—C24B—C23B | 129.9 (5) |
| C6A—C5A—H5AA | 119.0 | N5B—C24B—C23B | 105.6 (5) |
| C4A—C5A—H5AA | 119.0 | C30B—C25B—C26B | 118.0 (6) |
| C5A—C6A—C7A | 117.7 (7) | C30B—C25B—S1B | 120.8 (4) |
| C5A—C6A—H6AA | 121.1 | C26B—C25B—S1B | 121.3 (5) |
| C7A—C6A—H6AA | 121.1 | C27B—C26B—C25B | 120.5 (6) |
| C6A—C7A—C2A | 120.4 (6) | C27B—C26B—H26B | 119.7 |
| C6A—C7A—C8A | 132.5 (6) | C25B—C26B—H26B | 119.7 |
| C2A—C7A—C8A | 106.9 (5) | C26B—C27B—C28B | 122.5 (6) |
| N2A—C8A—N1A | 122.2 (5) | C26B—C27B—H27B | 118.8 |
| N2A—C8A—C7A | 130.2 (5) | C28B—C27B—H27B | 118.8 |
| N1A—C8A—C7A | 105.7 (5) | C27B—C28B—C29B | 116.8 (6) |
| N2A—C9A—N3A | 122.5 (5) | C27B—C28B—C31B | 122.1 (6) |
| N2A—C9A—C10A | 130.1 (5) | C29B—C28B—C31B | 121.1 (7) |
| N3A—C9A—C10A | 105.4 (5) | C30B—C29B—C28B | 120.9 (6) |
| C11A—C10A—C15A | 121.2 (6) | C30B—C29B—H29B | 119.6 |
| C11A—C10A—C9A | 131.7 (6) | C28B—C29B—H29B | 119.6 |
| C15A—C10A—C9A | 107.1 (5) | C25B—C30B—C29B | 121.1 (6) |
| C10A—C11A—C12A | 117.0 (6) | C25B—C30B—H30B | 119.5 |
| C10A—C11A—H11A | 121.5 | C29B—C30B—H30B | 119.5 |
| C12A—C11A—H11A | 121.5 | C28B—C31B—H31D | 109.5 |
| C13A—C12A—C11A | 121.9 (6) | C28B—C31B—H31E | 109.5 |
| C13A—C12A—H12A | 119.1 | H31D—C31B—H31E | 109.5 |
| C11A—C12A—H12A | 119.1 | C28B—C31B—H31F | 109.5 |
| C14A—C13A—C12A | 121.1 (6) | H31D—C31B—H31F | 109.5 |
| C14A—C13A—H13A | 119.5 | H31E—C31B—H31F | 109.5 |
| C12A—C13A—H13A | 119.5 | N1B—B1B—N5B | 104.1 (5) |
| C13A—C14A—C15A | 118.1 (6) | N1B—B1B—N3B | 103.7 (4) |
| C13A—C14A—H14A | 121.0 | N5B—B1B—N3B | 103.4 (4) |
| C15A—C14A—H14A | 121.0 | N1B—B1B—S1B | 112.1 (4) |
| C14A—C15A—C10A | 120.7 (6) | N5B—B1B—S1B | 114.5 (4) |
| C14A—C15A—C16A | 131.6 (6) | N3B—B1B—S1B | 117.5 (4) |
| C10A—C15A—C16A | 107.5 (5) | C25C—S1C—B1C | 101.4 (3) |
| N4A—C16A—N3A | 123.1 (5) | C1C—N1C—C8C | 113.5 (5) |
| N4A—C16A—C15A | 129.9 (5) | C1C—N1C—B1C | 123.5 (5) |
| N3A—C16A—C15A | 105.3 (5) | C8C—N1C—B1C | 122.2 (5) |
| N4A—C17A—N5A | 121.9 (5) | C8C—N2C—C9C | 116.7 (5) |
| N4A—C17A—C18A | 130.9 (5) | C16C—N3C—C9C | 112.6 (5) |
| N5A—C17A—C18A | 105.4 (5) | C16C—N3C—B1C | 123.3 (5) |
| C19A—C18A—C23A | 119.4 (6) | C9C—N3C—B1C | 123.3 (5) |
| C19A—C18A—C17A | 132.7 (6) | C16C—N4C—C17C | 116.8 (5) |
| C23A—C18A—C17A | 107.7 (5) | C17C—N5C—C24C | 112.9 (5) |
| C20A—C19A—C18A | 119.3 (6) | C17C—N5C—B1C | 123.1 (5) |
| C20A—C19A—H19A | 120.4 | C24C—N5C—B1C | 122.8 (5) |
| C18A—C19A—H19A | 120.4 | C1C—N6C—C24C | 117.3 (5) |
| C19A—C20A—C21A | 120.1 (6) | N6C—C1C—N1C | 122.0 (5) |
| C19A—C20A—H20A | 120.0 | N6C—C1C—C2C | 131.1 (6) |
| C21A—C20A—H20A | 120.0 | N1C—C1C—C2C | 104.9 (6) |
| C22A—C21A—C20A | 122.1 (7) | C3C—C2C—C7C | 120.8 (6) |
| C22A—C21A—H21A | 119.0 | C3C—C2C—C1C | 131.7 (7) |
| C20A—C21A—H21A | 119.0 | C7C—C2C—C1C | 107.5 (6) |
| C23A—C22A—C21A | 117.9 (6) | C4C—C3C—C2C | 117.5 (9) |
| C23A—C22A—H22A | 121.0 | C4C—C3C—H3C | 121.2 |
| C21A—C22A—H22A | 121.0 | C2C—C3C—H3C | 121.2 |
| C22A—C23A—C18A | 121.2 (6) | C3C—C4C—C5C | 120.9 (8) |
| C22A—C23A—C24A | 131.7 (6) | C3C—C4C—H4CA | 119.6 |
| C18A—C23A—C24A | 107.1 (5) | C5C—C4C—H4CA | 119.6 |
| N6A—C24A—N5A | 122.3 (5) | C6C—C5C—C4C | 123.3 (8) |
| N6A—C24A—C23A | 130.3 (5) | C6C—C5C—H5CA | 118.3 |
| N5A—C24A—C23A | 105.7 (5) | C4C—C5C—H5CA | 118.3 |
| C26A—C25A—C30A | 119.0 (6) | C5C—C6C—C7C | 116.8 (9) |
| C26A—C25A—S1A | 119.8 (5) | C5C—C6C—H6CA | 121.6 |
| C30A—C25A—S1A | 121.0 (4) | C7C—C6C—H6CA | 121.6 |
| C25A—C26A—C27A | 119.6 (6) | C2C—C7C—C6C | 120.4 (7) |
| C25A—C26A—H26A | 120.2 | C2C—C7C—C8C | 107.3 (5) |
| C27A—C26A—H26A | 120.2 | C6C—C7C—C8C | 132.2 (8) |
| C28A—C27A—C26A | 121.7 (6) | N2C—C8C—N1C | 123.0 (6) |
| C28A—C27A—H27A | 119.1 | N2C—C8C—C7C | 130.5 (6) |
| C26A—C27A—H27A | 119.1 | N1C—C8C—C7C | 105.5 (6) |
| C27A—C28A—C29A | 117.6 (6) | N2C—C9C—N3C | 122.0 (6) |
| C27A—C28A—C31A | 121.2 (6) | N2C—C9C—C10C | 130.7 (6) |
| C29A—C28A—C31A | 121.1 (6) | N3C—C9C—C10C | 105.8 (6) |
| C30A—C29A—C28A | 122.1 (6) | C11C—C10C—C15C | 120.0 (8) |
| C30A—C29A—H29A | 119.0 | C11C—C10C—C9C | 132.4 (7) |
| C28A—C29A—H29A | 119.0 | C15C—C10C—C9C | 107.5 (6) |
| C29A—C30A—C25A | 120.0 (6) | C12C—C11C—C10C | 117.6 (9) |
| C29A—C30A—H30A | 120.0 | C12C—C11C—H11C | 121.2 |
| C25A—C30A—H30A | 120.0 | C10C—C11C—H11C | 121.2 |
| C28A—C31A—H31A | 109.5 | C11C—C12C—C13C | 122.8 (9) |
| C28A—C31A—H31B | 109.5 | C11C—C12C—H12C | 118.6 |
| H31A—C31A—H31B | 109.5 | C13C—C12C—H12C | 118.6 |
| C28A—C31A—H31C | 109.5 | C14C—C13C—C12C | 119.6 (8) |
| H31A—C31A—H31C | 109.5 | C14C—C13C—H13C | 120.2 |
| H31B—C31A—H31C | 109.5 | C12C—C13C—H13C | 120.2 |
| N5A—B1A—N3A | 104.0 (5) | C15C—C14C—C13C | 118.4 (9) |
| N5A—B1A—N1A | 104.4 (5) | C15C—C14C—H14C | 120.8 |
| N3A—B1A—N1A | 104.2 (5) | C13C—C14C—H14C | 120.8 |
| N5A—B1A—S1A | 116.9 (4) | C14C—C15C—C10C | 121.6 (8) |
| N3A—B1A—S1A | 117.2 (4) | C14C—C15C—C16C | 131.5 (7) |
| N1A—B1A—S1A | 108.7 (4) | C10C—C15C—C16C | 106.8 (6) |
| C25B—S1B—B1B | 99.4 (3) | N4C—C16C—N3C | 122.2 (6) |
| C1B—N1B—C8B | 112.9 (4) | N4C—C16C—C15C | 130.6 (6) |
| C1B—N1B—B1B | 122.7 (5) | N3C—C16C—C15C | 105.9 (6) |
| C8B—N1B—B1B | 123.0 (4) | N4C—C17C—N5C | 122.5 (6) |
| C8B—N2B—C9B | 115.9 (5) | N4C—C17C—C18C | 130.2 (6) |
| C16B—N3B—C9B | 113.0 (4) | N5C—C17C—C18C | 105.5 (6) |
| C16B—N3B—B1B | 123.0 (5) | C23C—C18C—C19C | 121.1 (6) |
| C9B—N3B—B1B | 123.0 (4) | C23C—C18C—C17C | 107.5 (5) |
| C16B—N4B—C17B | 116.8 (4) | C19C—C18C—C17C | 131.1 (7) |
| C24B—N5B—C17B | 114.0 (5) | C20C—C19C—C18C | 117.5 (7) |
| C24B—N5B—B1B | 122.1 (5) | C20C—C19C—H19C | 121.3 |
| C17B—N5B—B1B | 123.3 (5) | C18C—C19C—H19C | 121.3 |
| C1B—N6B—C24B | 116.5 (5) | C19C—C20C—C21C | 121.2 (6) |
| N6B—C1B—N1B | 122.5 (5) | C19C—C20C—H20C | 119.4 |
| N6B—C1B—C2B | 130.2 (5) | C21C—C20C—H20C | 119.4 |
| N1B—C1B—C2B | 105.9 (5) | C22C—C21C—C20C | 121.7 (7) |
| C3B—C2B—C7B | 120.8 (5) | C22C—C21C—H21C | 119.1 |
| C3B—C2B—C1B | 131.7 (6) | C20C—C21C—H21C | 119.1 |
| C7B—C2B—C1B | 107.3 (5) | C21C—C22C—C23C | 117.8 (7) |
| C4B—C3B—C2B | 118.2 (5) | C21C—C22C—H22C | 121.1 |
| C4B—C3B—H3BA | 120.9 | C23C—C22C—H22C | 121.1 |
| C2B—C3B—H3BA | 120.9 | C18C—C23C—C22C | 120.7 (6) |
| C3B—C4B—C5B | 121.2 (5) | C18C—C23C—C24C | 108.0 (5) |
| C3B—C4B—H4BA | 119.4 | C22C—C23C—C24C | 130.7 (6) |
| C5B—C4B—H4BA | 119.4 | N6C—C24C—N5C | 122.1 (5) |
| C6B—C5B—C4B | 121.2 (5) | N6C—C24C—C23C | 131.9 (6) |
| C6B—C5B—H5BA | 119.4 | N5C—C24C—C23C | 104.6 (5) |
| C4B—C5B—H5BA | 119.4 | C26C—C25C—C30C | 117.9 (5) |
| C7B—C6B—C5B | 117.7 (5) | C26C—C25C—S1C | 120.1 (4) |
| C7B—C6B—H6BA | 121.2 | C30C—C25C—S1C | 121.9 (5) |
| C5B—C6B—H6BA | 121.2 | C25C—C26C—C27C | 121.1 (6) |
| C6B—C7B—C2B | 120.9 (5) | C25C—C26C—H26C | 119.4 |
| C6B—C7B—C8B | 131.3 (5) | C27C—C26C—H26C | 119.4 |
| C2B—C7B—C8B | 107.5 (5) | C28C—C27C—C26C | 121.4 (6) |
| N2B—C8B—N1B | 123.4 (5) | C28C—C27C—H27C | 119.3 |
| N2B—C8B—C7B | 130.4 (5) | C26C—C27C—H27C | 119.3 |
| N1B—C8B—C7B | 105.0 (4) | C27C—C28C—C29C | 117.3 (6) |
| N2B—C9B—N3B | 123.0 (5) | C27C—C28C—C31C | 120.8 (6) |
| N2B—C9B—C10B | 130.1 (5) | C29C—C28C—C31C | 121.9 (6) |
| N3B—C9B—C10B | 105.4 (5) | C30C—C29C—C28C | 121.4 (6) |
| C11B—C10B—C15B | 120.9 (5) | C30C—C29C—H29C | 119.3 |
| C11B—C10B—C9B | 131.8 (5) | C28C—C29C—H29C | 119.3 |
| C15B—C10B—C9B | 107.1 (5) | C29C—C30C—C25C | 120.8 (6) |
| C10B—C11B—C12B | 118.3 (6) | C29C—C30C—H30C | 119.6 |
| C10B—C11B—H11B | 120.9 | C25C—C30C—H30C | 119.6 |
| C12B—C11B—H11B | 120.9 | C28C—C31C—H31I | 109.5 |
| C11B—C12B—C13B | 120.7 (6) | C28C—C31C—H31J | 109.5 |
| C11B—C12B—H12B | 119.6 | H31I—C31C—H31J | 109.5 |
| C13B—C12B—H12B | 119.6 | C28C—C31C—H31G | 109.5 |
| C14B—C13B—C12B | 122.1 (5) | H31I—C31C—H31G | 109.5 |
| C14B—C13B—H13B | 119.0 | H31J—C31C—H31G | 109.5 |
| C12B—C13B—H13B | 119.0 | N5C—B1C—N3C | 103.9 (5) |
| C13B—C14B—C15B | 118.3 (6) | N5C—B1C—N1C | 103.7 (5) |
| C13B—C14B—H14B | 120.8 | N3C—B1C—N1C | 103.9 (5) |
| C15B—C14B—H14B | 120.8 | N5C—B1C—S1C | 116.9 (4) |
| C14B—C15B—C10B | 119.7 (5) | N3C—B1C—S1C | 116.1 (4) |
| C14B—C15B—C16B | 132.8 (6) | N1C—B1C—S1C | 110.8 (4) |
| C10B—C15B—C16B | 107.4 (4) | ||
| C24A—N6A—C1A—N1A | −8.7 (8) | C16B—N4B—C17B—N5B | −6.8 (8) |
| C24A—N6A—C1A—C2A | 154.1 (6) | C16B—N4B—C17B—C18B | 157.5 (6) |
| C8A—N1A—C1A—N6A | 155.5 (5) | C24B—N5B—C17B—N4B | 156.6 (5) |
| B1A—N1A—C1A—N6A | −11.3 (9) | B1B—N5B—C17B—N4B | −15.3 (8) |
| C8A—N1A—C1A—C2A | −10.8 (6) | C24B—N5B—C17B—C18B | −11.2 (6) |
| B1A—N1A—C1A—C2A | −177.6 (5) | B1B—N5B—C17B—C18B | 176.9 (5) |
| N6A—C1A—C2A—C3A | 15.5 (11) | N4B—C17B—C18B—C19B | 17.6 (11) |
| N1A—C1A—C2A—C3A | −179.3 (6) | N5B—C17B—C18B—C19B | −176.2 (6) |
| N6A—C1A—C2A—C7A | −159.9 (6) | N4B—C17B—C18B—C23B | −159.7 (6) |
| N1A—C1A—C2A—C7A | 5.3 (6) | N5B—C17B—C18B—C23B | 6.5 (6) |
| C7A—C2A—C3A—C4A | −1.7 (9) | C23B—C18B—C19B—C20B | −0.9 (9) |
| C1A—C2A—C3A—C4A | −176.5 (6) | C17B—C18B—C19B—C20B | −177.9 (6) |
| C2A—C3A—C4A—C5A | 0.2 (10) | C18B—C19B—C20B—C21B | 1.2 (10) |
| C3A—C4A—C5A—C6A | 1.9 (10) | C19B—C20B—C21B—C22B | −0.2 (11) |
| C4A—C5A—C6A—C7A | −2.4 (10) | C20B—C21B—C22B—C23B | −1.3 (10) |
| C5A—C6A—C7A—C2A | 0.9 (9) | C21B—C22B—C23B—C18B | 1.6 (9) |
| C5A—C6A—C7A—C8A | 175.1 (6) | C21B—C22B—C23B—C24B | 178.4 (6) |
| C3A—C2A—C7A—C6A | 1.1 (9) | C19B—C18B—C23B—C22B | −0.5 (9) |
| C1A—C2A—C7A—C6A | 177.1 (5) | C17B—C18B—C23B—C22B | 177.2 (5) |
| C3A—C2A—C7A—C8A | −174.4 (6) | C19B—C18B—C23B—C24B | −178.0 (5) |
| C1A—C2A—C7A—C8A | 1.6 (7) | C17B—C18B—C23B—C24B | −0.4 (6) |
| C9A—N2A—C8A—N1A | 8.1 (8) | C1B—N6B—C24B—N5B | 7.5 (8) |
| C9A—N2A—C8A—C7A | −154.0 (6) | C1B—N6B—C24B—C23B | −155.4 (6) |
| C1A—N1A—C8A—N2A | −154.1 (6) | C17B—N5B—C24B—N6B | −155.5 (5) |
| B1A—N1A—C8A—N2A | 12.6 (9) | B1B—N5B—C24B—N6B | 16.5 (8) |
| C1A—N1A—C8A—C7A | 11.8 (7) | C17B—N5B—C24B—C23B | 11.0 (6) |
| B1A—N1A—C8A—C7A | 178.5 (5) | B1B—N5B—C24B—C23B | −177.0 (5) |
| C6A—C7A—C8A—N2A | −18.2 (11) | C22B—C23B—C24B—N6B | −17.9 (11) |
| C2A—C7A—C8A—N2A | 156.6 (6) | C18B—C23B—C24B—N6B | 159.2 (6) |
| C6A—C7A—C8A—N1A | 177.5 (6) | C22B—C23B—C24B—N5B | 176.9 (6) |
| C2A—C7A—C8A—N1A | −7.8 (6) | C18B—C23B—C24B—N5B | −6.0 (6) |
| C8A—N2A—C9A—N3A | −7.7 (8) | B1B—S1B—C25B—C30B | −107.4 (5) |
| C8A—N2A—C9A—C10A | 154.2 (6) | B1B—S1B—C25B—C26B | 71.7 (5) |
| C16A—N3A—C9A—N2A | 155.0 (6) | C30B—C25B—C26B—C27B | 5.0 (9) |
| B1A—N3A—C9A—N2A | −13.6 (9) | S1B—C25B—C26B—C27B | −174.2 (5) |
| C16A—N3A—C9A—C10A | −10.7 (7) | C25B—C26B—C27B—C28B | −0.9 (9) |
| B1A—N3A—C9A—C10A | −179.3 (5) | C26B—C27B—C28B—C29B | −3.1 (9) |
| N2A—C9A—C10A—C11A | 18.6 (11) | C26B—C27B—C28B—C31B | 175.0 (6) |
| N3A—C9A—C10A—C11A | −177.2 (6) | C27B—C28B—C29B—C30B | 3.1 (10) |
| N2A—C9A—C10A—C15A | −158.9 (6) | C31B—C28B—C29B—C30B | −175.1 (6) |
| N3A—C9A—C10A—C15A | 5.3 (6) | C26B—C25B—C30B—C29B | −5.0 (9) |
| C15A—C10A—C11A—C12A | −1.6 (9) | S1B—C25B—C30B—C29B | 174.2 (5) |
| C9A—C10A—C11A—C12A | −178.9 (6) | C28B—C29B—C30B—C25B | 1.0 (10) |
| C10A—C11A—C12A—C13A | 1.5 (10) | C1B—N1B—B1B—N5B | 30.1 (6) |
| C11A—C12A—C13A—C14A | 0.5 (10) | C8B—N1B—B1B—N5B | −135.6 (5) |
| C12A—C13A—C14A—C15A | −2.3 (10) | C1B—N1B—B1B—N3B | 138.0 (5) |
| C13A—C14A—C15A—C10A | 2.1 (9) | C8B—N1B—B1B—N3B | −27.7 (7) |
| C13A—C14A—C15A—C16A | 177.6 (6) | C1B—N1B—B1B—S1B | −94.2 (5) |
| C11A—C10A—C15A—C14A | −0.2 (9) | C8B—N1B—B1B—S1B | 100.1 (5) |
| C9A—C10A—C15A—C14A | 177.7 (6) | C24B—N5B—B1B—N1B | −32.4 (7) |
| C11A—C10A—C15A—C16A | −176.6 (6) | C17B—N5B—B1B—N1B | 138.9 (5) |
| C9A—C10A—C15A—C16A | 1.3 (7) | C24B—N5B—B1B—N3B | −140.5 (5) |
| C17A—N4A—C16A—N3A | 7.3 (8) | C17B—N5B—B1B—N3B | 30.8 (7) |
| C17A—N4A—C16A—C15A | −155.9 (6) | C24B—N5B—B1B—S1B | 90.4 (6) |
| C9A—N3A—C16A—N4A | −155.3 (6) | C17B—N5B—B1B—S1B | −98.3 (5) |
| B1A—N3A—C16A—N4A | 13.4 (9) | C16B—N3B—B1B—N1B | −138.3 (5) |
| C9A—N3A—C16A—C15A | 11.4 (7) | C9B—N3B—B1B—N1B | 29.7 (7) |
| B1A—N3A—C16A—C15A | −179.9 (5) | C16B—N3B—B1B—N5B | −29.8 (6) |
| C14A—C15A—C16A—N4A | −17.8 (11) | C9B—N3B—B1B—N5B | 138.1 (5) |
| C10A—C15A—C16A—N4A | 158.1 (6) | C16B—N3B—B1B—S1B | 97.4 (6) |
| C14A—C15A—C16A—N3A | 176.7 (6) | C9B—N3B—B1B—S1B | −94.7 (6) |
| C10A—C15A—C16A—N3A | −7.4 (6) | C24C—N6C—C1C—N1C | −7.0 (8) |
| C16A—N4A—C17A—N5A | −6.7 (8) | C24C—N6C—C1C—C2C | 154.9 (6) |
| C16A—N4A—C17A—C18A | 155.9 (6) | C8C—N1C—C1C—N6C | 154.1 (5) |
| C24A—N5A—C17A—N4A | 154.9 (5) | B1C—N1C—C1C—N6C | −15.8 (9) |
| B1A—N5A—C17A—N4A | −14.8 (8) | C8C—N1C—C1C—C2C | −11.8 (6) |
| C24A—N5A—C17A—C18A | −11.6 (6) | B1C—N1C—C1C—C2C | 178.3 (5) |
| B1A—N5A—C17A—C18A | 178.7 (5) | N6C—C1C—C2C—C3C | 20.4 (11) |
| N4A—C17A—C18A—C19A | 18.6 (11) | N1C—C1C—C2C—C3C | −175.5 (6) |
| N5A—C17A—C18A—C19A | −176.7 (6) | N6C—C1C—C2C—C7C | −157.0 (6) |
| N4A—C17A—C18A—C23A | −157.8 (6) | N1C—C1C—C2C—C7C | 7.1 (6) |
| N5A—C17A—C18A—C23A | 7.0 (6) | C7C—C2C—C3C—C4C | −3.1 (9) |
| C23A—C18A—C19A—C20A | −2.2 (9) | C1C—C2C—C3C—C4C | 179.8 (6) |
| C17A—C18A—C19A—C20A | −178.2 (6) | C2C—C3C—C4C—C5C | 5.6 (10) |
| C18A—C19A—C20A—C21A | 1.7 (9) | C3C—C4C—C5C—C6C | −3.8 (12) |
| C19A—C20A—C21A—C22A | 0.0 (10) | C4C—C5C—C6C—C7C | −0.9 (11) |
| C20A—C21A—C22A—C23A | −1.2 (9) | C3C—C2C—C7C—C6C | −1.4 (9) |
| C21A—C22A—C23A—C18A | 0.7 (9) | C1C—C2C—C7C—C6C | 176.3 (6) |
| C21A—C22A—C23A—C24A | 178.6 (6) | C3C—C2C—C7C—C8C | −178.3 (5) |
| C19A—C18A—C23A—C22A | 0.9 (9) | C1C—C2C—C7C—C8C | −0.6 (7) |
| C17A—C18A—C23A—C22A | 177.9 (5) | C5C—C6C—C7C—C2C | 3.4 (9) |
| C19A—C18A—C23A—C24A | −177.4 (5) | C5C—C6C—C7C—C8C | 179.3 (7) |
| C17A—C18A—C23A—C24A | −0.5 (6) | C9C—N2C—C8C—N1C | 9.8 (9) |
| C1A—N6A—C24A—N5A | 7.2 (8) | C9C—N2C—C8C—C7C | −157.2 (6) |
| C1A—N6A—C24A—C23A | −155.6 (6) | C1C—N1C—C8C—N2C | −158.3 (6) |
| C17A—N5A—C24A—N6A | −155.1 (5) | B1C—N1C—C8C—N2C | 11.8 (9) |
| B1A—N5A—C24A—N6A | 14.6 (8) | C1C—N1C—C8C—C7C | 11.5 (6) |
| C17A—N5A—C24A—C23A | 11.3 (6) | B1C—N1C—C8C—C7C | −178.4 (5) |
| B1A—N5A—C24A—C23A | −179.0 (5) | C2C—C7C—C8C—N2C | 162.5 (6) |
| C22A—C23A—C24A—N6A | −19.4 (11) | C6C—C7C—C8C—N2C | −13.8 (11) |
| C18A—C23A—C24A—N6A | 158.7 (6) | C2C—C7C—C8C—N1C | −6.2 (6) |
| C22A—C23A—C24A—N5A | 175.7 (6) | C6C—C7C—C8C—N1C | 177.5 (6) |
| C18A—C23A—C24A—N5A | −6.2 (6) | C8C—N2C—C9C—N3C | −8.3 (9) |
| B1A—S1A—C25A—C26A | 112.4 (5) | C8C—N2C—C9C—C10C | 155.3 (7) |
| B1A—S1A—C25A—C30A | −72.8 (5) | C16C—N3C—C9C—N2C | 155.0 (6) |
| C30A—C25A—C26A—C27A | −0.1 (9) | B1C—N3C—C9C—N2C | −15.2 (9) |
| S1A—C25A—C26A—C27A | 174.8 (5) | C16C—N3C—C9C—C10C | −12.1 (7) |
| C25A—C26A—C27A—C28A | 0.1 (10) | B1C—N3C—C9C—C10C | 177.7 (5) |
| C26A—C27A—C28A—C29A | 0.0 (10) | N2C—C9C—C10C—C11C | 18.6 (13) |
| C26A—C27A—C28A—C31A | 177.0 (6) | N3C—C9C—C10C—C11C | −175.9 (8) |
| C27A—C28A—C29A—C30A | −0.1 (9) | N2C—C9C—C10C—C15C | −157.6 (7) |
| C31A—C28A—C29A—C30A | −177.1 (6) | N3C—C9C—C10C—C15C | 7.9 (7) |
| C28A—C29A—C30A—C25A | 0.1 (9) | C15C—C10C—C11C—C12C | −1.2 (11) |
| C26A—C25A—C30A—C29A | 0.1 (9) | C9C—C10C—C11C—C12C | −177.1 (8) |
| S1A—C25A—C30A—C29A | −174.8 (4) | C10C—C11C—C12C—C13C | 2.7 (13) |
| C24A—N5A—B1A—N3A | −138.6 (5) | C11C—C12C—C13C—C14C | −1.6 (14) |
| C17A—N5A—B1A—N3A | 30.1 (7) | C12C—C13C—C14C—C15C | −1.1 (12) |
| C24A—N5A—B1A—N1A | −29.5 (7) | C13C—C14C—C15C—C10C | 2.5 (11) |
| C17A—N5A—B1A—N1A | 139.1 (5) | C13C—C14C—C15C—C16C | 178.4 (7) |
| C24A—N5A—B1A—S1A | 90.5 (6) | C11C—C10C—C15C—C14C | −1.4 (11) |
| C17A—N5A—B1A—S1A | −100.8 (6) | C9C—C10C—C15C—C14C | 175.4 (6) |
| C16A—N3A—B1A—N5A | −29.4 (7) | C11C—C10C—C15C—C16C | −178.2 (6) |
| C9A—N3A—B1A—N5A | 138.2 (5) | C9C—C10C—C15C—C16C | −1.4 (8) |
| C16A—N3A—B1A—N1A | −138.5 (5) | C17C—N4C—C16C—N3C | 8.5 (9) |
| C9A—N3A—B1A—N1A | 29.1 (7) | C17C—N4C—C16C—C15C | −156.6 (7) |
| C16A—N3A—B1A—S1A | 101.4 (6) | C9C—N3C—C16C—N4C | −157.1 (6) |
| C9A—N3A—B1A—S1A | −91.0 (6) | B1C—N3C—C16C—N4C | 13.1 (9) |
| C1A—N1A—B1A—N5A | 27.9 (7) | C9C—N3C—C16C—C15C | 11.3 (7) |
| C8A—N1A—B1A—N5A | −137.6 (5) | B1C—N3C—C16C—C15C | −178.5 (5) |
| C1A—N1A—B1A—N3A | 136.8 (5) | C14C—C15C—C16C—N4C | −15.0 (12) |
| C8A—N1A—B1A—N3A | −28.7 (7) | C10C—C15C—C16C—N4C | 161.3 (7) |
| C1A—N1A—B1A—S1A | −97.5 (6) | C14C—C15C—C16C—N3C | 178.0 (7) |
| C8A—N1A—B1A—S1A | 97.0 (6) | C10C—C15C—C16C—N3C | −5.6 (7) |
| C24B—N6B—C1B—N1B | −10.0 (8) | C16C—N4C—C17C—N5C | −8.6 (9) |
| C24B—N6B—C1B—C2B | 154.2 (6) | C16C—N4C—C17C—C18C | 154.3 (6) |
| C8B—N1B—C1B—N6B | 155.5 (5) | C24C—N5C—C17C—N4C | 154.8 (6) |
| B1B—N1B—C1B—N6B | −11.5 (8) | B1C—N5C—C17C—N4C | −13.0 (9) |
| C8B—N1B—C1B—C2B | −12.0 (6) | C24C—N5C—C17C—C18C | −11.7 (6) |
| B1B—N1B—C1B—C2B | −179.0 (5) | B1C—N5C—C17C—C18C | −179.5 (5) |
| N6B—C1B—C2B—C3B | 16.3 (10) | N4C—C17C—C18C—C23C | −158.7 (6) |
| N1B—C1B—C2B—C3B | −177.5 (6) | N5C—C17C—C18C—C23C | 6.3 (6) |
| N6B—C1B—C2B—C7B | −159.3 (6) | N4C—C17C—C18C—C19C | 15.6 (11) |
| N1B—C1B—C2B—C7B | 6.9 (6) | N5C—C17C—C18C—C19C | −179.3 (6) |
| C7B—C2B—C3B—C4B | −1.0 (8) | C23C—C18C—C19C—C20C | 0.2 (9) |
| C1B—C2B—C3B—C4B | −176.2 (6) | C17C—C18C—C19C—C20C | −173.5 (6) |
| C2B—C3B—C4B—C5B | 1.6 (8) | C18C—C19C—C20C—C21C | 0.0 (10) |
| C3B—C4B—C5B—C6B | 0.3 (9) | C19C—C20C—C21C—C22C | 1.1 (11) |
| C4B—C5B—C6B—C7B | −2.7 (8) | C20C—C21C—C22C—C23C | −2.3 (10) |
| C5B—C6B—C7B—C2B | 3.2 (8) | C19C—C18C—C23C—C22C | −1.5 (9) |
| C5B—C6B—C7B—C8B | 176.4 (6) | C17C—C18C—C23C—C22C | 173.5 (6) |
| C3B—C2B—C7B—C6B | −1.4 (8) | C19C—C18C—C23C—C24C | −174.3 (6) |
| C1B—C2B—C7B—C6B | 174.8 (5) | C17C—C18C—C23C—C24C | 0.8 (7) |
| C3B—C2B—C7B—C8B | −176.1 (5) | C21C—C22C—C23C—C18C | 2.5 (9) |
| C1B—C2B—C7B—C8B | 0.1 (6) | C21C—C22C—C23C—C24C | 173.4 (6) |
| C9B—N2B—C8B—N1B | 10.1 (8) | C1C—N6C—C24C—N5C | 8.8 (8) |
| C9B—N2B—C8B—C7B | −155.2 (6) | C1C—N6C—C24C—C23C | −155.5 (6) |
| C1B—N1B—C8B—N2B | −156.5 (5) | C17C—N5C—C24C—N6C | −155.8 (5) |
| B1B—N1B—C8B—N2B | 10.4 (8) | B1C—N5C—C24C—N6C | 12.0 (9) |
| C1B—N1B—C8B—C7B | 12.0 (6) | C17C—N5C—C24C—C23C | 12.1 (6) |
| B1B—N1B—C8B—C7B | 178.9 (5) | B1C—N5C—C24C—C23C | 180.0 (5) |
| C6B—C7B—C8B—N2B | −13.4 (10) | C18C—C23C—C24C—N6C | 158.8 (6) |
| C2B—C7B—C8B—N2B | 160.4 (6) | C22C—C23C—C24C—N6C | −13.0 (12) |
| C6B—C7B—C8B—N1B | 179.2 (6) | C18C—C23C—C24C—N5C | −7.4 (6) |
| C2B—C7B—C8B—N1B | −7.0 (6) | C22C—C23C—C24C—N5C | −179.2 (6) |
| C8B—N2B—C9B—N3B | −8.1 (8) | B1C—S1C—C25C—C26C | 82.0 (5) |
| C8B—N2B—C9B—C10B | 155.8 (6) | B1C—S1C—C25C—C30C | −102.3 (5) |
| C16B—N3B—C9B—N2B | 154.6 (5) | C30C—C25C—C26C—C27C | 1.2 (9) |
| B1B—N3B—C9B—N2B | −14.5 (8) | S1C—C25C—C26C—C27C | 177.0 (5) |
| C16B—N3B—C9B—C10B | −12.7 (6) | C25C—C26C—C27C—C28C | −0.2 (10) |
| B1B—N3B—C9B—C10B | 178.2 (5) | C26C—C27C—C28C—C29C | −0.9 (9) |
| N2B—C9B—C10B—C11B | 15.7 (10) | C26C—C27C—C28C—C31C | 178.3 (6) |
| N3B—C9B—C10B—C11B | −178.2 (6) | C27C—C28C—C29C—C30C | 0.9 (9) |
| N2B—C9B—C10B—C15B | −158.7 (6) | C31C—C28C—C29C—C30C | −178.3 (6) |
| N3B—C9B—C10B—C15B | 7.4 (6) | C28C—C29C—C30C—C25C | 0.1 (9) |
| C15B—C10B—C11B—C12B | −2.0 (8) | C26C—C25C—C30C—C29C | −1.1 (9) |
| C9B—C10B—C11B—C12B | −175.8 (6) | S1C—C25C—C30C—C29C | −176.9 (5) |
| C10B—C11B—C12B—C13B | 1.7 (9) | C17C—N5C—B1C—N3C | 29.2 (7) |
| C11B—C12B—C13B—C14B | 0.2 (10) | C24C—N5C—B1C—N3C | −137.4 (5) |
| C12B—C13B—C14B—C15B | −1.6 (9) | C17C—N5C—B1C—N1C | 137.6 (5) |
| C13B—C14B—C15B—C10B | 1.3 (8) | C24C—N5C—B1C—N1C | −29.0 (7) |
| C13B—C14B—C15B—C16B | 175.8 (6) | C17C—N5C—B1C—S1C | −100.0 (6) |
| C11B—C10B—C15B—C14B | 0.5 (8) | C24C—N5C—B1C—S1C | 93.4 (6) |
| C9B—C10B—C15B—C14B | 175.7 (5) | C16C—N3C—B1C—N5C | −29.4 (7) |
| C11B—C10B—C15B—C16B | −175.2 (5) | C9C—N3C—B1C—N5C | 139.8 (5) |
| C9B—C10B—C15B—C16B | −0.1 (6) | C16C—N3C—B1C—N1C | −137.6 (5) |
| C17B—N4B—C16B—N3B | 7.6 (8) | C9C—N3C—B1C—N1C | 31.5 (7) |
| C17B—N4B—C16B—C15B | −157.3 (5) | C16C—N3C—B1C—S1C | 100.4 (6) |
| C9B—N3B—C16B—N4B | −155.5 (5) | C9C—N3C—B1C—S1C | −90.4 (6) |
| B1B—N3B—C16B—N4B | 13.6 (8) | C1C—N1C—B1C—N5C | 31.1 (7) |
| C9B—N3B—C16B—C15B | 12.7 (6) | C8C—N1C—B1C—N5C | −138.0 (5) |
| B1B—N3B—C16B—C15B | −178.3 (5) | C1C—N1C—B1C—N3C | 139.5 (5) |
| C14B—C15B—C16B—N4B | −15.3 (10) | C8C—N1C—B1C—N3C | −29.6 (7) |
| C10B—C15B—C16B—N4B | 159.7 (6) | C1C—N1C—B1C—S1C | −95.2 (6) |
| C14B—C15B—C16B—N3B | 177.8 (6) | C8C—N1C—B1C—S1C | 95.7 (6) |
| C10B—C15B—C16B—N3B | −7.2 (6) |
(N-Phenylbenzamido)(subphthalocyaninato)boron (d2339_a) top
Crystal data top
| C31H20BN7·0.14H2O | Z = 4 |
| Mr = 503.87 | F(000) = 1046 |
| Triclinic, P1 | Dx = 1.385 Mg m−3 |
| a = 11.4897 (5) Å | Cu Kα radiation, λ = 1.54178 Å |
| b = 11.7489 (5) Å | Cell parameters from 9824 reflections |
| c = 19.3046 (8) Å | θ = 4.0–65.7° |
| α = 73.348 (2)° | µ = 0.68 mm−1 |
| β = 81.941 (2)° | T = 150 K |
| γ = 76.167 (2)° | Shard, pink |
| V = 2417.05 (18) Å3 | 0.20 × 0.15 × 0.08 mm |
Data collection top
| Bruker Kappa APEX-DUO CMOS PHOTON II diffractometer | 7193 reflections with I > 2σ(I) |
| Radiation source: Incoatec ImuS with multi-layer optics | Rint = 0.046 |
| φ and ω scans | θmax = 66.0°, θmin = 2.4° |
| Absorption correction: multi-scan SADABS (Krause et al., 2015) | h = −13→13 |
| Tmin = 0.657, Tmax = 0.753 | k = −13→13 |
| 60606 measured reflections | l = −22→22 |
| 8275 independent reflections |
Refinement top
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Hydrogen site location: mixed |
| R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
| wR(F2) = 0.093 | w = 1/[σ2(Fo2) + (0.0453P)2 + 0.687P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.06 | (Δ/σ)max < 0.001 |
| 8275 reflections | Δρmax = 0.27 e Å−3 |
| 713 parameters | Δρmin = −0.29 e Å−3 |
| 0 restraints |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | Occ. (<1) | |
| N1 | −0.01647 (9) | 0.70429 (10) | 0.08430 (6) | 0.0216 (2) | |
| N2 | −0.00691 (9) | 0.49963 (10) | 0.15298 (6) | 0.0228 (2) | |
| N3 | 0.16519 (9) | 0.58812 (10) | 0.13041 (6) | 0.0229 (2) | |
| N4 | 0.29543 (10) | 0.68828 (11) | 0.16512 (6) | 0.0279 (3) | |
| N5 | 0.13649 (10) | 0.80098 (10) | 0.09047 (6) | 0.0240 (2) | |
| N6 | −0.06157 (10) | 0.91739 (10) | 0.06937 (6) | 0.0250 (2) | |
| N7 | 0.16020 (10) | 0.68676 (10) | −0.00712 (6) | 0.0251 (2) | |
| C1 | −0.09554 (11) | 0.81378 (12) | 0.07385 (7) | 0.0230 (3) | |
| C2 | −0.21422 (12) | 0.78506 (13) | 0.08656 (7) | 0.0251 (3) | |
| C3 | −0.32857 (13) | 0.85814 (14) | 0.07843 (8) | 0.0332 (3) | |
| H3A | −0.339567 | 0.943705 | 0.059301 | 0.040* | |
| C4 | −0.42578 (13) | 0.80261 (15) | 0.09901 (9) | 0.0385 (4) | |
| H4A | −0.504640 | 0.850486 | 0.092060 | 0.046* | |
| C5 | −0.41054 (13) | 0.67746 (15) | 0.12984 (9) | 0.0365 (4) | |
| H5A | −0.479314 | 0.642303 | 0.144975 | 0.044* | |
| C6 | −0.29758 (12) | 0.60402 (13) | 0.13871 (8) | 0.0280 (3) | |
| H6A | −0.287886 | 0.519170 | 0.160426 | 0.034* | |
| C7 | −0.19825 (11) | 0.65711 (12) | 0.11511 (7) | 0.0230 (3) | |
| C8 | −0.06908 (11) | 0.60808 (12) | 0.11715 (7) | 0.0218 (3) | |
| C9 | 0.10872 (11) | 0.49409 (12) | 0.16254 (7) | 0.0231 (3) | |
| C10 | 0.18630 (12) | 0.41069 (13) | 0.21727 (7) | 0.0252 (3) | |
| C11 | 0.17561 (13) | 0.30096 (13) | 0.26734 (8) | 0.0291 (3) | |
| H11A | 0.110620 | 0.263722 | 0.267657 | 0.035* | |
| C12 | 0.26251 (14) | 0.24755 (14) | 0.31676 (8) | 0.0355 (3) | |
| H12A | 0.257140 | 0.172320 | 0.351045 | 0.043* | |
| C13 | 0.35778 (14) | 0.30231 (15) | 0.31706 (9) | 0.0383 (4) | |
| H13A | 0.416995 | 0.262606 | 0.350776 | 0.046* | |
| C14 | 0.36757 (13) | 0.41301 (14) | 0.26931 (8) | 0.0329 (3) | |
| H14A | 0.431531 | 0.450678 | 0.270490 | 0.039* | |
| C15 | 0.28107 (12) | 0.46783 (13) | 0.21940 (8) | 0.0272 (3) | |
| C16 | 0.25890 (11) | 0.58633 (13) | 0.16753 (7) | 0.0259 (3) | |
| C17 | 0.22837 (11) | 0.79456 (13) | 0.13026 (7) | 0.0264 (3) | |
| C18 | 0.21547 (12) | 0.91685 (13) | 0.13773 (8) | 0.0286 (3) | |
| C19 | 0.28483 (13) | 0.96887 (15) | 0.16923 (8) | 0.0352 (4) | |
| H19A | 0.356331 | 0.922151 | 0.191056 | 0.042* | |
| C20 | 0.24601 (15) | 1.09026 (15) | 0.16757 (9) | 0.0388 (4) | |
| H20A | 0.293367 | 1.128054 | 0.187015 | 0.047* | |
| C21 | 0.13861 (15) | 1.15892 (15) | 0.13793 (8) | 0.0374 (4) | |
| H21A | 0.114973 | 1.242308 | 0.137504 | 0.045* | |
| C22 | 0.06604 (14) | 1.10814 (13) | 0.10922 (8) | 0.0322 (3) | |
| H22A | −0.008343 | 1.154240 | 0.090895 | 0.039* | |
| C23 | 0.10615 (12) | 0.98678 (13) | 0.10819 (7) | 0.0270 (3) | |
| C24 | 0.05306 (12) | 0.90673 (12) | 0.08295 (7) | 0.0242 (3) | |
| C25 | 0.28121 (12) | 0.69402 (13) | −0.03300 (7) | 0.0254 (3) | |
| C26 | 0.36217 (13) | 0.59752 (14) | −0.05290 (8) | 0.0315 (3) | |
| H26A | 0.336981 | 0.524086 | −0.048062 | 0.038* | |
| C27 | 0.47876 (14) | 0.60706 (15) | −0.07962 (9) | 0.0386 (4) | |
| H27A | 0.531879 | 0.540775 | −0.093837 | 0.046* | |
| C28 | 0.51855 (14) | 0.71100 (15) | −0.08581 (9) | 0.0408 (4) | |
| H28A | 0.599024 | 0.716652 | −0.103336 | 0.049* | |
| C29 | 0.43931 (14) | 0.80749 (15) | −0.06607 (9) | 0.0384 (4) | |
| H29A | 0.466225 | 0.879469 | −0.069503 | 0.046* | |
| C30 | 0.32135 (13) | 0.80070 (14) | −0.04137 (8) | 0.0317 (3) | |
| H30A | 0.267394 | 0.869113 | −0.030052 | 0.038* | |
| C31 | 0.11511 (13) | 0.59755 (14) | −0.02957 (8) | 0.0319 (3) | |
| H31A | 0.031735 | 0.598047 | −0.009695 | 0.048* | |
| H31B | 0.118520 | 0.618280 | −0.082630 | 0.048* | |
| H31C | 0.164840 | 0.516517 | −0.011427 | 0.048* | |
| B1 | 0.11629 (13) | 0.69448 (14) | 0.06916 (8) | 0.0237 (3) | |
| N8 | 0.80208 (10) | 0.22661 (10) | 0.44369 (6) | 0.0248 (2) | |
| N9 | 0.97660 (10) | 0.31154 (11) | 0.40625 (6) | 0.0273 (3) | |
| N10 | 0.79477 (10) | 0.40585 (10) | 0.34885 (6) | 0.0249 (2) | |
| N11 | 0.60890 (10) | 0.54894 (11) | 0.33121 (6) | 0.0289 (3) | |
| N12 | 0.61599 (10) | 0.34840 (10) | 0.40642 (6) | 0.0247 (2) | |
| N13 | 0.62459 (10) | 0.20647 (11) | 0.52258 (6) | 0.0275 (3) | |
| N14 | 0.74153 (10) | 0.23329 (10) | 0.31662 (6) | 0.0258 (3) | |
| C32 | 0.74483 (12) | 0.17952 (12) | 0.50877 (7) | 0.0259 (3) | |
| C33 | 0.83819 (13) | 0.12217 (12) | 0.55928 (8) | 0.0277 (3) | |
| C34 | 0.83378 (14) | 0.05840 (13) | 0.63239 (8) | 0.0329 (3) | |
| H34A | 0.760386 | 0.041292 | 0.657945 | 0.040* | |
| C35 | 0.93989 (14) | 0.02096 (14) | 0.66637 (8) | 0.0369 (4) | |
| H35A | 0.939374 | −0.023987 | 0.715860 | 0.044* | |
| C36 | 1.04779 (14) | 0.04769 (14) | 0.62961 (8) | 0.0361 (3) | |
| H36A | 1.119249 | 0.019380 | 0.654424 | 0.043* | |
| C37 | 1.05289 (13) | 0.11445 (13) | 0.55789 (8) | 0.0319 (3) | |
| H37A | 1.126004 | 0.134737 | 0.533697 | 0.038* | |
| C38 | 0.94727 (12) | 0.15113 (13) | 0.52213 (8) | 0.0274 (3) | |
| C39 | 0.91895 (12) | 0.22814 (13) | 0.45033 (7) | 0.0257 (3) | |
| C40 | 0.91044 (12) | 0.40437 (13) | 0.35936 (7) | 0.0256 (3) | |
| C41 | 0.92861 (13) | 0.52674 (13) | 0.32510 (7) | 0.0275 (3) | |
| C42 | 1.02796 (14) | 0.57922 (14) | 0.31861 (8) | 0.0327 (3) | |
| H42A | 1.102593 | 0.531800 | 0.335909 | 0.039* | |
| C43 | 1.01408 (16) | 0.70269 (15) | 0.28612 (8) | 0.0402 (4) | |
| H43A | 1.081017 | 0.739948 | 0.279910 | 0.048* | |
| C44 | 0.90370 (17) | 0.77357 (15) | 0.26230 (8) | 0.0411 (4) | |
| H44A | 0.897586 | 0.857825 | 0.239768 | 0.049* | |
| C45 | 0.80302 (15) | 0.72415 (14) | 0.27068 (8) | 0.0345 (3) | |
| H45A | 0.727590 | 0.773501 | 0.255953 | 0.041* | |
| C46 | 0.81619 (13) | 0.59917 (13) | 0.30156 (7) | 0.0285 (3) | |
| C47 | 0.73002 (12) | 0.52042 (13) | 0.32209 (7) | 0.0267 (3) | |
| C48 | 0.55510 (12) | 0.46415 (13) | 0.37720 (7) | 0.0273 (3) | |
| C49 | 0.43838 (12) | 0.47681 (14) | 0.41828 (8) | 0.0309 (3) | |
| C50 | 0.33515 (13) | 0.56869 (15) | 0.40909 (9) | 0.0380 (4) | |
| H50A | 0.333399 | 0.641871 | 0.371602 | 0.046* | |
| C51 | 0.23524 (14) | 0.54967 (17) | 0.45645 (10) | 0.0448 (4) | |
| H51A | 0.162836 | 0.609666 | 0.450205 | 0.054* | |
| C52 | 0.23860 (14) | 0.44417 (18) | 0.51322 (9) | 0.0454 (4) | |
| H52A | 0.167837 | 0.433276 | 0.544077 | 0.054* | |
| C53 | 0.34236 (13) | 0.35509 (16) | 0.52568 (8) | 0.0369 (4) | |
| H53A | 0.345181 | 0.285741 | 0.566037 | 0.044* | |
| C54 | 0.44269 (12) | 0.37063 (14) | 0.47694 (8) | 0.0302 (3) | |
| C55 | 0.56274 (12) | 0.29493 (13) | 0.47186 (7) | 0.0264 (3) | |
| C56 | 0.67307 (12) | 0.14705 (12) | 0.32086 (7) | 0.0251 (3) | |
| C57 | 0.64720 (14) | 0.12150 (14) | 0.25856 (8) | 0.0339 (3) | |
| H57A | 0.676114 | 0.163778 | 0.212068 | 0.041* | |
| C58 | 0.57979 (15) | 0.03512 (15) | 0.26419 (9) | 0.0417 (4) | |
| H58A | 0.563730 | 0.019383 | 0.221245 | 0.050* | |
| C59 | 0.53559 (15) | −0.02839 (15) | 0.33041 (9) | 0.0400 (4) | |
| H59A | 0.488893 | −0.086606 | 0.333504 | 0.048* | |
| C60 | 0.56122 (13) | −0.00485 (14) | 0.39217 (9) | 0.0345 (3) | |
| H60A | 0.531533 | −0.047420 | 0.438366 | 0.041* | |
| C61 | 0.62956 (12) | 0.07987 (13) | 0.38775 (8) | 0.0290 (3) | |
| H61A | 0.647346 | 0.092735 | 0.431168 | 0.035* | |
| C62 | 0.81233 (14) | 0.26659 (14) | 0.24757 (8) | 0.0348 (3) | |
| H62A | 0.857108 | 0.326886 | 0.249300 | 0.052* | |
| H62B | 0.868840 | 0.194126 | 0.238969 | 0.052* | |
| H62C | 0.758458 | 0.301048 | 0.208202 | 0.052* | |
| B2 | 0.73887 (14) | 0.29648 (14) | 0.37514 (8) | 0.0247 (3) | |
| O1W | 0.4210 (4) | 0.7569 (3) | 0.2715 (2) | 0.0384 (14) | 0.281 (4) |
| H2O | 0.387836 | 0.725753 | 0.247583 | 0.058* | 0.281 (4) |
| H1O | 0.485406 | 0.707403 | 0.283633 | 0.058* | 0.281 (4) |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N1 | 0.0188 (5) | 0.0265 (6) | 0.0220 (5) | −0.0075 (4) | −0.0001 (4) | −0.0087 (4) |
| N2 | 0.0196 (5) | 0.0282 (6) | 0.0233 (6) | −0.0059 (5) | −0.0010 (4) | −0.0106 (5) |
| N3 | 0.0171 (5) | 0.0301 (6) | 0.0251 (6) | −0.0064 (5) | 0.0001 (4) | −0.0123 (5) |
| N4 | 0.0179 (5) | 0.0392 (7) | 0.0320 (6) | −0.0086 (5) | 0.0017 (5) | −0.0176 (5) |
| N5 | 0.0208 (5) | 0.0308 (6) | 0.0248 (6) | −0.0109 (5) | 0.0034 (4) | −0.0124 (5) |
| N6 | 0.0264 (6) | 0.0283 (6) | 0.0218 (6) | −0.0089 (5) | 0.0002 (4) | −0.0073 (5) |
| N7 | 0.0225 (6) | 0.0321 (6) | 0.0259 (6) | −0.0114 (5) | 0.0034 (4) | −0.0136 (5) |
| C1 | 0.0223 (7) | 0.0280 (7) | 0.0196 (6) | −0.0061 (5) | −0.0009 (5) | −0.0072 (5) |
| C2 | 0.0218 (7) | 0.0321 (7) | 0.0236 (7) | −0.0061 (6) | −0.0014 (5) | −0.0107 (6) |
| C3 | 0.0255 (7) | 0.0339 (8) | 0.0405 (9) | −0.0023 (6) | −0.0054 (6) | −0.0123 (7) |
| C4 | 0.0191 (7) | 0.0449 (9) | 0.0527 (10) | −0.0011 (6) | −0.0036 (6) | −0.0191 (8) |
| C5 | 0.0200 (7) | 0.0466 (9) | 0.0471 (9) | −0.0113 (6) | 0.0027 (6) | −0.0178 (7) |
| C6 | 0.0220 (7) | 0.0352 (8) | 0.0297 (7) | −0.0101 (6) | 0.0005 (5) | −0.0110 (6) |
| C7 | 0.0201 (6) | 0.0316 (7) | 0.0207 (6) | −0.0072 (5) | −0.0005 (5) | −0.0113 (5) |
| C8 | 0.0200 (6) | 0.0282 (7) | 0.0209 (6) | −0.0088 (5) | 0.0002 (5) | −0.0101 (5) |
| C9 | 0.0202 (6) | 0.0288 (7) | 0.0241 (7) | −0.0065 (5) | 0.0004 (5) | −0.0128 (6) |
| C10 | 0.0222 (7) | 0.0305 (7) | 0.0261 (7) | −0.0019 (6) | −0.0017 (5) | −0.0154 (6) |
| C11 | 0.0291 (7) | 0.0304 (8) | 0.0295 (7) | −0.0016 (6) | −0.0030 (6) | −0.0138 (6) |
| C12 | 0.0400 (9) | 0.0331 (8) | 0.0323 (8) | 0.0004 (7) | −0.0085 (6) | −0.0109 (6) |
| C13 | 0.0337 (8) | 0.0441 (9) | 0.0377 (9) | 0.0048 (7) | −0.0145 (7) | −0.0171 (7) |
| C14 | 0.0233 (7) | 0.0435 (9) | 0.0357 (8) | −0.0004 (6) | −0.0073 (6) | −0.0194 (7) |
| C15 | 0.0203 (7) | 0.0355 (8) | 0.0291 (7) | −0.0012 (6) | −0.0012 (5) | −0.0178 (6) |
| C16 | 0.0159 (6) | 0.0375 (8) | 0.0286 (7) | −0.0056 (6) | 0.0004 (5) | −0.0166 (6) |
| C17 | 0.0181 (6) | 0.0393 (8) | 0.0279 (7) | −0.0119 (6) | 0.0043 (5) | −0.0166 (6) |
| C18 | 0.0261 (7) | 0.0373 (8) | 0.0287 (7) | −0.0153 (6) | 0.0075 (6) | −0.0159 (6) |
| C19 | 0.0285 (8) | 0.0501 (10) | 0.0377 (8) | −0.0188 (7) | 0.0065 (6) | −0.0241 (7) |
| C20 | 0.0427 (9) | 0.0500 (10) | 0.0384 (9) | −0.0278 (8) | 0.0090 (7) | −0.0252 (7) |
| C21 | 0.0519 (10) | 0.0351 (8) | 0.0326 (8) | −0.0208 (7) | 0.0064 (7) | −0.0156 (7) |
| C22 | 0.0420 (8) | 0.0322 (8) | 0.0255 (7) | −0.0149 (7) | 0.0045 (6) | −0.0102 (6) |
| C23 | 0.0299 (7) | 0.0331 (8) | 0.0225 (7) | −0.0151 (6) | 0.0063 (5) | −0.0116 (6) |
| C24 | 0.0249 (7) | 0.0284 (7) | 0.0212 (7) | −0.0094 (6) | 0.0034 (5) | −0.0087 (5) |
| C25 | 0.0236 (7) | 0.0326 (7) | 0.0204 (7) | −0.0079 (6) | 0.0021 (5) | −0.0078 (6) |
| C26 | 0.0307 (8) | 0.0319 (8) | 0.0314 (8) | −0.0069 (6) | 0.0024 (6) | −0.0095 (6) |
| C27 | 0.0303 (8) | 0.0391 (9) | 0.0407 (9) | −0.0014 (7) | 0.0075 (7) | −0.0109 (7) |
| C28 | 0.0252 (8) | 0.0478 (10) | 0.0441 (9) | −0.0102 (7) | 0.0092 (7) | −0.0073 (7) |
| C29 | 0.0322 (8) | 0.0405 (9) | 0.0440 (9) | −0.0172 (7) | 0.0091 (7) | −0.0112 (7) |
| C30 | 0.0286 (7) | 0.0341 (8) | 0.0345 (8) | −0.0117 (6) | 0.0084 (6) | −0.0133 (6) |
| C31 | 0.0328 (8) | 0.0401 (8) | 0.0308 (8) | −0.0156 (6) | 0.0038 (6) | −0.0185 (7) |
| B1 | 0.0198 (7) | 0.0294 (8) | 0.0254 (8) | −0.0088 (6) | 0.0003 (6) | −0.0106 (6) |
| N8 | 0.0233 (6) | 0.0289 (6) | 0.0234 (6) | −0.0076 (5) | 0.0000 (4) | −0.0077 (5) |
| N9 | 0.0240 (6) | 0.0332 (6) | 0.0255 (6) | −0.0074 (5) | 0.0019 (5) | −0.0097 (5) |
| N10 | 0.0263 (6) | 0.0281 (6) | 0.0218 (6) | −0.0079 (5) | −0.0008 (4) | −0.0077 (5) |
| N11 | 0.0318 (6) | 0.0318 (6) | 0.0260 (6) | −0.0059 (5) | −0.0070 (5) | −0.0103 (5) |
| N12 | 0.0220 (6) | 0.0306 (6) | 0.0236 (6) | −0.0067 (5) | −0.0017 (4) | −0.0097 (5) |
| N13 | 0.0264 (6) | 0.0346 (7) | 0.0250 (6) | −0.0118 (5) | −0.0003 (5) | −0.0096 (5) |
| N14 | 0.0267 (6) | 0.0294 (6) | 0.0231 (6) | −0.0102 (5) | 0.0018 (5) | −0.0077 (5) |
| C32 | 0.0281 (7) | 0.0278 (7) | 0.0236 (7) | −0.0106 (6) | −0.0001 (5) | −0.0068 (6) |
| C33 | 0.0299 (7) | 0.0256 (7) | 0.0278 (7) | −0.0069 (6) | −0.0023 (6) | −0.0067 (6) |
| C34 | 0.0374 (8) | 0.0312 (8) | 0.0294 (8) | −0.0102 (6) | −0.0029 (6) | −0.0041 (6) |
| C35 | 0.0443 (9) | 0.0334 (8) | 0.0289 (8) | −0.0047 (7) | −0.0083 (7) | −0.0019 (6) |
| C36 | 0.0350 (8) | 0.0346 (8) | 0.0360 (8) | 0.0019 (6) | −0.0107 (7) | −0.0090 (7) |
| C37 | 0.0276 (7) | 0.0328 (8) | 0.0349 (8) | −0.0023 (6) | −0.0043 (6) | −0.0109 (6) |
| C38 | 0.0279 (7) | 0.0272 (7) | 0.0276 (7) | −0.0047 (6) | −0.0018 (6) | −0.0092 (6) |
| C39 | 0.0214 (7) | 0.0304 (7) | 0.0264 (7) | −0.0055 (6) | 0.0008 (5) | −0.0104 (6) |
| C40 | 0.0240 (7) | 0.0331 (8) | 0.0225 (7) | −0.0094 (6) | 0.0029 (5) | −0.0114 (6) |
| C41 | 0.0332 (7) | 0.0344 (8) | 0.0189 (7) | −0.0136 (6) | 0.0042 (5) | −0.0106 (6) |
| C42 | 0.0366 (8) | 0.0415 (9) | 0.0266 (7) | −0.0181 (7) | 0.0081 (6) | −0.0161 (6) |
| C43 | 0.0512 (10) | 0.0451 (9) | 0.0339 (8) | −0.0285 (8) | 0.0106 (7) | −0.0170 (7) |
| C44 | 0.0643 (11) | 0.0335 (8) | 0.0300 (8) | −0.0227 (8) | 0.0044 (7) | −0.0087 (7) |
| C45 | 0.0502 (9) | 0.0318 (8) | 0.0236 (7) | −0.0124 (7) | −0.0015 (6) | −0.0078 (6) |
| C46 | 0.0388 (8) | 0.0311 (8) | 0.0191 (7) | −0.0123 (6) | 0.0001 (6) | −0.0089 (6) |
| C47 | 0.0319 (7) | 0.0299 (7) | 0.0200 (7) | −0.0073 (6) | −0.0040 (5) | −0.0077 (6) |
| C48 | 0.0274 (7) | 0.0318 (8) | 0.0265 (7) | −0.0047 (6) | −0.0073 (6) | −0.0123 (6) |
| C49 | 0.0260 (7) | 0.0404 (8) | 0.0332 (8) | −0.0049 (6) | −0.0057 (6) | −0.0203 (7) |
| C50 | 0.0317 (8) | 0.0450 (9) | 0.0448 (9) | 0.0003 (7) | −0.0108 (7) | −0.0266 (8) |
| C51 | 0.0289 (8) | 0.0640 (12) | 0.0515 (10) | 0.0036 (8) | −0.0078 (7) | −0.0395 (9) |
| C52 | 0.0278 (8) | 0.0780 (13) | 0.0415 (10) | −0.0077 (8) | 0.0032 (7) | −0.0387 (10) |
| C53 | 0.0280 (8) | 0.0594 (10) | 0.0320 (8) | −0.0119 (7) | 0.0021 (6) | −0.0252 (7) |
| C54 | 0.0240 (7) | 0.0440 (9) | 0.0299 (8) | −0.0085 (6) | −0.0020 (6) | −0.0197 (7) |
| C55 | 0.0249 (7) | 0.0345 (8) | 0.0248 (7) | −0.0115 (6) | 0.0004 (5) | −0.0125 (6) |
| C56 | 0.0219 (7) | 0.0245 (7) | 0.0292 (7) | −0.0032 (5) | −0.0021 (5) | −0.0087 (6) |
| C57 | 0.0388 (8) | 0.0356 (8) | 0.0299 (8) | −0.0121 (7) | −0.0039 (6) | −0.0086 (6) |
| C58 | 0.0504 (10) | 0.0444 (9) | 0.0395 (9) | −0.0178 (8) | −0.0089 (7) | −0.0164 (7) |
| C59 | 0.0406 (9) | 0.0365 (9) | 0.0496 (10) | −0.0175 (7) | −0.0039 (7) | −0.0137 (7) |
| C60 | 0.0337 (8) | 0.0326 (8) | 0.0376 (8) | −0.0113 (6) | 0.0027 (6) | −0.0089 (7) |
| C61 | 0.0290 (7) | 0.0298 (7) | 0.0301 (8) | −0.0074 (6) | 0.0002 (6) | −0.0110 (6) |
| C62 | 0.0422 (9) | 0.0388 (9) | 0.0273 (8) | −0.0176 (7) | 0.0069 (6) | −0.0117 (6) |
| B2 | 0.0233 (8) | 0.0268 (8) | 0.0238 (8) | −0.0071 (6) | −0.0001 (6) | −0.0060 (6) |
| O1W | 0.045 (2) | 0.032 (2) | 0.038 (2) | 0.0009 (17) | −0.0176 (17) | −0.0095 (17) |
Geometric parameters (Å, º) top
| N1—C8 | 1.3616 (17) | N8—C39 | 1.3714 (17) |
| N1—C1 | 1.3655 (17) | N8—B2 | 1.5213 (19) |
| N1—B1 | 1.4952 (18) | N9—C39 | 1.3408 (18) |
| N2—C8 | 1.3455 (17) | N9—C40 | 1.3481 (18) |
| N2—C9 | 1.3505 (17) | N10—C47 | 1.3648 (18) |
| N3—C9 | 1.3651 (17) | N10—C40 | 1.3676 (17) |
| N3—C16 | 1.3675 (16) | N10—B2 | 1.5002 (19) |
| N3—B1 | 1.5096 (19) | N11—C48 | 1.3404 (19) |
| N4—C17 | 1.3451 (19) | N11—C47 | 1.3498 (18) |
| N4—C16 | 1.3475 (18) | N12—C48 | 1.3687 (18) |
| N5—C24 | 1.3601 (18) | N12—C55 | 1.3701 (18) |
| N5—C17 | 1.3661 (17) | N12—B2 | 1.5134 (19) |
| N5—B1 | 1.4997 (19) | N13—C55 | 1.3425 (18) |
| N6—C1 | 1.3413 (17) | N13—C32 | 1.3475 (18) |
| N6—C24 | 1.3484 (17) | N14—C56 | 1.4026 (17) |
| N7—C25 | 1.4238 (17) | N14—C62 | 1.4632 (18) |
| N7—C31 | 1.4622 (17) | N14—B2 | 1.5128 (19) |
| N7—B1 | 1.5093 (18) | C32—C33 | 1.4583 (19) |
| C1—C2 | 1.4533 (18) | C33—C34 | 1.396 (2) |
| C2—C3 | 1.389 (2) | C33—C38 | 1.419 (2) |
| C2—C7 | 1.421 (2) | C34—C35 | 1.383 (2) |
| C3—C4 | 1.381 (2) | C34—H34A | 0.9500 |
| C3—H3A | 0.9500 | C35—C36 | 1.397 (2) |
| C4—C5 | 1.397 (2) | C35—H35A | 0.9500 |
| C4—H4A | 0.9500 | C36—C37 | 1.383 (2) |
| C5—C6 | 1.379 (2) | C36—H36A | 0.9500 |
| C5—H5A | 0.9500 | C37—C38 | 1.396 (2) |
| C6—C7 | 1.3896 (19) | C37—H37A | 0.9500 |
| C6—H6A | 0.9500 | C38—C39 | 1.4534 (19) |
| C7—C8 | 1.4596 (18) | C40—C41 | 1.452 (2) |
| C9—C10 | 1.4573 (19) | C41—C42 | 1.397 (2) |
| C10—C11 | 1.393 (2) | C41—C46 | 1.420 (2) |
| C10—C15 | 1.4199 (19) | C42—C43 | 1.385 (2) |
| C11—C12 | 1.387 (2) | C42—H42A | 0.9500 |
| C11—H11A | 0.9500 | C43—C44 | 1.397 (3) |
| C12—C13 | 1.397 (2) | C43—H43A | 0.9500 |
| C12—H12A | 0.9500 | C44—C45 | 1.384 (2) |
| C13—C14 | 1.381 (2) | C44—H44A | 0.9500 |
| C13—H13A | 0.9500 | C45—C46 | 1.397 (2) |
| C14—C15 | 1.392 (2) | C45—H45A | 0.9500 |
| C14—H14A | 0.9500 | C46—C47 | 1.453 (2) |
| C15—C16 | 1.452 (2) | C48—C49 | 1.457 (2) |
| C17—C18 | 1.455 (2) | C49—C50 | 1.393 (2) |
| C18—C19 | 1.400 (2) | C49—C54 | 1.420 (2) |
| C18—C23 | 1.420 (2) | C50—C51 | 1.384 (2) |
| C19—C20 | 1.381 (2) | C50—H50A | 0.9500 |
| C19—H19A | 0.9500 | C51—C52 | 1.396 (3) |
| C20—C21 | 1.399 (2) | C51—H51A | 0.9500 |
| C20—H20A | 0.9500 | C52—C53 | 1.383 (2) |
| C21—C22 | 1.384 (2) | C52—H52A | 0.9500 |
| C21—H21A | 0.9500 | C53—C54 | 1.395 (2) |
| C22—C23 | 1.395 (2) | C53—H53A | 0.9500 |
| C22—H22A | 0.9500 | C54—C55 | 1.459 (2) |
| C23—C24 | 1.4541 (19) | C56—C61 | 1.401 (2) |
| C25—C26 | 1.394 (2) | C56—C57 | 1.405 (2) |
| C25—C30 | 1.396 (2) | C57—C58 | 1.389 (2) |
| C26—C27 | 1.385 (2) | C57—H57A | 0.9500 |
| C26—H26A | 0.9500 | C58—C59 | 1.379 (2) |
| C27—C28 | 1.372 (2) | C58—H58A | 0.9500 |
| C27—H27A | 0.9500 | C59—C60 | 1.382 (2) |
| C28—C29 | 1.384 (2) | C59—H59A | 0.9500 |
| C28—H28A | 0.9500 | C60—C61 | 1.386 (2) |
| C29—C30 | 1.385 (2) | C60—H60A | 0.9500 |
| C29—H29A | 0.9500 | C61—H61A | 0.9500 |
| C30—H30A | 0.9500 | C62—H62A | 0.9800 |
| C31—H31A | 0.9800 | C62—H62B | 0.9800 |
| C31—H31B | 0.9800 | C62—H62C | 0.9800 |
| C31—H31C | 0.9800 | O1W—H2O | 0.8401 |
| N8—C32 | 1.3642 (17) | O1W—H1O | 0.8400 |
| C8—N1—C1 | 113.38 (10) | C32—N8—B2 | 124.40 (11) |
| C8—N1—B1 | 124.01 (11) | C39—N8—B2 | 122.09 (11) |
| C1—N1—B1 | 122.20 (11) | C39—N9—C40 | 116.86 (11) |
| C8—N2—C9 | 116.50 (11) | C47—N10—C40 | 112.78 (11) |
| C9—N3—C16 | 112.49 (11) | C47—N10—B2 | 122.91 (11) |
| C9—N3—B1 | 123.58 (11) | C40—N10—B2 | 123.59 (12) |
| C16—N3—B1 | 123.03 (11) | C48—N11—C47 | 116.64 (12) |
| C17—N4—C16 | 117.11 (11) | C48—N12—C55 | 112.39 (11) |
| C24—N5—C17 | 113.28 (11) | C48—N12—B2 | 122.23 (11) |
| C24—N5—B1 | 122.27 (11) | C55—N12—B2 | 124.57 (11) |
| C17—N5—B1 | 123.49 (12) | C55—N13—C32 | 116.47 (12) |
| C1—N6—C24 | 116.38 (11) | C56—N14—C62 | 114.88 (11) |
| C25—N7—C31 | 114.43 (11) | C56—N14—B2 | 124.55 (11) |
| C25—N7—B1 | 119.69 (11) | C62—N14—B2 | 120.43 (11) |
| C31—N7—B1 | 113.68 (11) | N13—C32—N8 | 123.15 (12) |
| N6—C1—N1 | 122.43 (11) | N13—C32—C33 | 129.25 (12) |
| N6—C1—C2 | 130.60 (12) | N8—C32—C33 | 106.29 (11) |
| N1—C1—C2 | 105.39 (11) | C34—C33—C38 | 120.82 (13) |
| C3—C2—C7 | 120.80 (12) | C34—C33—C32 | 132.17 (13) |
| C3—C2—C1 | 131.97 (13) | C38—C33—C32 | 106.80 (12) |
| C7—C2—C1 | 107.17 (11) | C35—C34—C33 | 117.74 (14) |
| C4—C3—C2 | 117.96 (14) | C35—C34—H34A | 121.1 |
| C4—C3—H3A | 121.0 | C33—C34—H34A | 121.1 |
| C2—C3—H3A | 121.0 | C34—C35—C36 | 121.53 (14) |
| C3—C4—C5 | 121.35 (14) | C34—C35—H35A | 119.2 |
| C3—C4—H4A | 119.3 | C36—C35—H35A | 119.2 |
| C5—C4—H4A | 119.3 | C37—C36—C35 | 121.44 (14) |
| C6—C5—C4 | 121.23 (13) | C37—C36—H36A | 119.3 |
| C6—C5—H5A | 119.4 | C35—C36—H36A | 119.3 |
| C4—C5—H5A | 119.4 | C36—C37—C38 | 117.95 (14) |
| C5—C6—C7 | 118.40 (14) | C36—C37—H37A | 121.0 |
| C5—C6—H6A | 120.8 | C38—C37—H37A | 121.0 |
| C7—C6—H6A | 120.8 | C37—C38—C33 | 120.45 (13) |
| C6—C7—C2 | 120.12 (12) | C37—C38—C39 | 132.18 (13) |
| C6—C7—C8 | 132.66 (13) | C33—C38—C39 | 107.11 (12) |
| C2—C7—C8 | 107.08 (11) | N9—C39—N8 | 122.90 (12) |
| N2—C8—N1 | 122.62 (11) | N9—C39—C38 | 128.68 (12) |
| N2—C8—C7 | 131.06 (12) | N8—C39—C38 | 106.02 (11) |
| N1—C8—C7 | 105.40 (11) | N9—C40—N10 | 122.31 (12) |
| N2—C9—N3 | 122.39 (12) | N9—C40—C41 | 130.29 (12) |
| N2—C9—C10 | 130.04 (12) | N10—C40—C41 | 105.90 (12) |
| N3—C9—C10 | 106.02 (11) | C42—C41—C46 | 120.67 (13) |
| C11—C10—C15 | 120.29 (12) | C42—C41—C40 | 131.84 (14) |
| C11—C10—C9 | 132.45 (12) | C46—C41—C40 | 107.24 (12) |
| C15—C10—C9 | 106.92 (12) | C43—C42—C41 | 117.82 (15) |
| C12—C11—C10 | 118.15 (14) | C43—C42—H42A | 121.1 |
| C12—C11—H11A | 120.9 | C41—C42—H42A | 121.1 |
| C10—C11—H11A | 120.9 | C42—C43—C44 | 121.38 (14) |
| C11—C12—C13 | 121.26 (15) | C42—C43—H43A | 119.3 |
| C11—C12—H12A | 119.4 | C44—C43—H43A | 119.3 |
| C13—C12—H12A | 119.4 | C45—C44—C43 | 121.67 (15) |
| C14—C13—C12 | 121.31 (14) | C45—C44—H44A | 119.2 |
| C14—C13—H13A | 119.3 | C43—C44—H44A | 119.2 |
| C12—C13—H13A | 119.3 | C44—C45—C46 | 117.69 (15) |
| C13—C14—C15 | 118.13 (14) | C44—C45—H45A | 121.2 |
| C13—C14—H14A | 120.9 | C46—C45—H45A | 121.2 |
| C15—C14—H14A | 120.9 | C45—C46—C41 | 120.69 (13) |
| C14—C15—C10 | 120.79 (14) | C45—C46—C47 | 132.07 (14) |
| C14—C15—C16 | 131.87 (13) | C41—C46—C47 | 107.03 (12) |
| C10—C15—C16 | 107.13 (11) | N11—C47—N10 | 122.46 (12) |
| N4—C16—N3 | 122.16 (13) | N11—C47—C46 | 129.81 (13) |
| N4—C16—C15 | 129.87 (12) | N10—C47—C46 | 106.02 (12) |
| N3—C16—C15 | 105.96 (11) | N11—C48—N12 | 122.61 (12) |
| N4—C17—N5 | 122.55 (12) | N11—C48—C49 | 130.11 (13) |
| N4—C17—C18 | 130.64 (12) | N12—C48—C49 | 105.88 (12) |
| N5—C17—C18 | 105.45 (12) | C50—C49—C54 | 120.88 (14) |
| C19—C18—C23 | 120.20 (14) | C50—C49—C48 | 132.12 (15) |
| C19—C18—C17 | 132.59 (14) | C54—C49—C48 | 107.00 (12) |
| C23—C18—C17 | 107.15 (11) | C51—C50—C49 | 117.69 (16) |
| C20—C19—C18 | 117.89 (15) | C51—C50—H50A | 121.2 |
| C20—C19—H19A | 121.1 | C49—C50—H50A | 121.2 |
| C18—C19—H19A | 121.1 | C50—C51—C52 | 121.40 (15) |
| C19—C20—C21 | 121.59 (14) | C50—C51—H51A | 119.3 |
| C19—C20—H20A | 119.2 | C52—C51—H51A | 119.3 |
| C21—C20—H20A | 119.2 | C53—C52—C51 | 121.67 (15) |
| C22—C21—C20 | 121.52 (15) | C53—C52—H52A | 119.2 |
| C22—C21—H21A | 119.2 | C51—C52—H52A | 119.2 |
| C20—C21—H21A | 119.2 | C52—C53—C54 | 117.69 (16) |
| C21—C22—C23 | 117.53 (15) | C52—C53—H53A | 121.2 |
| C21—C22—H22A | 121.2 | C54—C53—H53A | 121.2 |
| C23—C22—H22A | 121.2 | C53—C54—C49 | 120.51 (14) |
| C22—C23—C18 | 121.17 (13) | C53—C54—C55 | 132.38 (15) |
| C22—C23—C24 | 131.68 (13) | C49—C54—C55 | 107.10 (12) |
| C18—C23—C24 | 107.11 (12) | N13—C55—N12 | 122.55 (12) |
| N6—C24—N5 | 123.03 (12) | N13—C55—C54 | 130.57 (13) |
| N6—C24—C23 | 129.86 (12) | N12—C55—C54 | 105.60 (12) |
| N5—C24—C23 | 105.70 (11) | C61—C56—N14 | 121.49 (12) |
| C26—C25—C30 | 117.79 (13) | C61—C56—C57 | 116.67 (13) |
| C26—C25—N7 | 121.72 (12) | N14—C56—C57 | 121.82 (12) |
| C30—C25—N7 | 120.46 (12) | C58—C57—C56 | 120.76 (14) |
| C27—C26—C25 | 121.02 (14) | C58—C57—H57A | 119.6 |
| C27—C26—H26A | 119.5 | C56—C57—H57A | 119.6 |
| C25—C26—H26A | 119.5 | C59—C58—C57 | 121.78 (15) |
| C28—C27—C26 | 120.85 (15) | C59—C58—H58A | 119.1 |
| C28—C27—H27A | 119.6 | C57—C58—H58A | 119.1 |
| C26—C27—H27A | 119.6 | C58—C59—C60 | 118.05 (14) |
| C27—C28—C29 | 118.79 (14) | C58—C59—H59A | 121.0 |
| C27—C28—H28A | 120.6 | C60—C59—H59A | 121.0 |
| C29—C28—H28A | 120.6 | C59—C60—C61 | 121.04 (14) |
| C28—C29—C30 | 121.02 (15) | C59—C60—H60A | 119.5 |
| C28—C29—H29A | 119.5 | C61—C60—H60A | 119.5 |
| C30—C29—H29A | 119.5 | C60—C61—C56 | 121.67 (13) |
| C29—C30—C25 | 120.46 (14) | C60—C61—H61A | 119.2 |
| C29—C30—H30A | 119.8 | C56—C61—H61A | 119.2 |
| C25—C30—H30A | 119.8 | N14—C62—H62A | 109.5 |
| N7—C31—H31A | 109.5 | N14—C62—H62B | 109.5 |
| N7—C31—H31B | 109.5 | H62A—C62—H62B | 109.5 |
| H31A—C31—H31B | 109.5 | N14—C62—H62C | 109.5 |
| N7—C31—H31C | 109.5 | H62A—C62—H62C | 109.5 |
| H31A—C31—H31C | 109.5 | H62B—C62—H62C | 109.5 |
| H31B—C31—H31C | 109.5 | N10—B2—N14 | 112.75 (11) |
| N1—B1—N5 | 102.87 (11) | N10—B2—N12 | 102.23 (11) |
| N1—B1—N7 | 113.06 (11) | N14—B2—N12 | 116.53 (11) |
| N5—B1—N7 | 116.61 (11) | N10—B2—N8 | 102.36 (11) |
| N1—B1—N3 | 102.27 (11) | N14—B2—N8 | 119.22 (12) |
| N5—B1—N3 | 102.77 (11) | N12—B2—N8 | 101.40 (11) |
| N7—B1—N3 | 117.25 (12) | H2O—O1W—H1O | 106.2 |
| C32—N8—C39 | 112.03 (11) | ||
| C24—N6—C1—N1 | −6.41 (18) | C55—N13—C32—N8 | −8.12 (19) |
| C24—N6—C1—C2 | 157.01 (13) | C55—N13—C32—C33 | 156.97 (14) |
| C8—N1—C1—N6 | 153.70 (12) | C39—N8—C32—N13 | 155.20 (13) |
| B1—N1—C1—N6 | −19.18 (19) | B2—N8—C32—N13 | −11.1 (2) |
| C8—N1—C1—C2 | −13.32 (14) | C39—N8—C32—C33 | −12.83 (15) |
| B1—N1—C1—C2 | 173.80 (11) | B2—N8—C32—C33 | −179.16 (12) |
| N6—C1—C2—C3 | 20.4 (2) | N13—C32—C33—C34 | 14.1 (3) |
| N1—C1—C2—C3 | −174.04 (14) | N8—C32—C33—C34 | −178.85 (15) |
| N6—C1—C2—C7 | −156.65 (13) | N13—C32—C33—C38 | −160.50 (14) |
| N1—C1—C2—C7 | 8.88 (14) | N8—C32—C33—C38 | 6.53 (15) |
| C7—C2—C3—C4 | 0.1 (2) | C38—C33—C34—C35 | −2.2 (2) |
| C1—C2—C3—C4 | −176.66 (14) | C32—C33—C34—C35 | −176.24 (15) |
| C2—C3—C4—C5 | 2.6 (2) | C33—C34—C35—C36 | 1.2 (2) |
| C3—C4—C5—C6 | −2.2 (2) | C34—C35—C36—C37 | 1.0 (2) |
| C4—C5—C6—C7 | −1.0 (2) | C35—C36—C37—C38 | −2.2 (2) |
| C5—C6—C7—C2 | 3.6 (2) | C36—C37—C38—C33 | 1.2 (2) |
| C5—C6—C7—C8 | 178.76 (14) | C36—C37—C38—C39 | 174.66 (15) |
| C3—C2—C7—C6 | −3.2 (2) | C34—C33—C38—C37 | 1.1 (2) |
| C1—C2—C7—C6 | 174.25 (12) | C32—C33—C38—C37 | 176.42 (13) |
| C3—C2—C7—C8 | −179.48 (12) | C34—C33—C38—C39 | −173.89 (13) |
| C1—C2—C7—C8 | −2.02 (14) | C32—C33—C38—C39 | 1.47 (15) |
| C9—N2—C8—N1 | 7.69 (18) | C40—N9—C39—N8 | 7.64 (19) |
| C9—N2—C8—C7 | −159.65 (13) | C40—N9—C39—C38 | −152.21 (14) |
| C1—N1—C8—N2 | −158.07 (12) | C32—N8—C39—N9 | −150.03 (13) |
| B1—N1—C8—N2 | 14.66 (19) | B2—N8—C39—N9 | 16.7 (2) |
| C1—N1—C8—C7 | 12.06 (14) | C32—N8—C39—C38 | 13.73 (15) |
| B1—N1—C8—C7 | −175.21 (11) | B2—N8—C39—C38 | −179.58 (12) |
| C6—C7—C8—N2 | −12.3 (2) | C37—C38—C39—N9 | −20.5 (3) |
| C2—C7—C8—N2 | 163.34 (13) | C33—C38—C39—N9 | 153.60 (14) |
| C6—C7—C8—N1 | 178.77 (14) | C37—C38—C39—N8 | 176.99 (15) |
| C2—C7—C8—N1 | −5.62 (14) | C33—C38—C39—N8 | −8.90 (15) |
| C8—N2—C9—N3 | −7.82 (18) | C39—N9—C40—N10 | −9.49 (19) |
| C8—N2—C9—C10 | 155.91 (13) | C39—N9—C40—C41 | 154.45 (14) |
| C16—N3—C9—N2 | 155.30 (12) | C47—N10—C40—N9 | 157.11 (12) |
| B1—N3—C9—N2 | −14.09 (19) | B2—N10—C40—N9 | −13.4 (2) |
| C16—N3—C9—C10 | −11.81 (14) | C47—N10—C40—C41 | −10.22 (15) |
| B1—N3—C9—C10 | 178.80 (11) | B2—N10—C40—C41 | 179.28 (12) |
| N2—C9—C10—C11 | 13.2 (2) | N9—C40—C41—C42 | 13.8 (2) |
| N3—C9—C10—C11 | 178.95 (14) | N10—C40—C41—C42 | 179.78 (14) |
| N2—C9—C10—C15 | −159.83 (13) | N9—C40—C41—C46 | −160.26 (14) |
| N3—C9—C10—C15 | 5.93 (14) | N10—C40—C41—C46 | 5.67 (14) |
| C15—C10—C11—C12 | −2.7 (2) | C46—C41—C42—C43 | −2.4 (2) |
| C9—C10—C11—C12 | −174.92 (14) | C40—C41—C42—C43 | −175.84 (14) |
| C10—C11—C12—C13 | 0.6 (2) | C41—C42—C43—C44 | 1.7 (2) |
| C11—C12—C13—C14 | 1.5 (2) | C42—C43—C44—C45 | 0.7 (2) |
| C12—C13—C14—C15 | −1.4 (2) | C43—C44—C45—C46 | −2.3 (2) |
| C13—C14—C15—C10 | −0.7 (2) | C44—C45—C46—C41 | 1.6 (2) |
| C13—C14—C15—C16 | 173.40 (14) | C44—C45—C46—C47 | 175.55 (14) |
| C11—C10—C15—C14 | 2.8 (2) | C42—C41—C46—C45 | 0.7 (2) |
| C9—C10—C15—C14 | 176.81 (12) | C40—C41—C46—C45 | 175.62 (12) |
| C11—C10—C15—C16 | −172.62 (12) | C42—C41—C46—C47 | −174.55 (12) |
| C9—C10—C15—C16 | 1.43 (14) | C40—C41—C46—C47 | 0.35 (14) |
| C17—N4—C16—N3 | 6.41 (19) | C48—N11—C47—N10 | 9.80 (18) |
| C17—N4—C16—C15 | −155.14 (13) | C48—N11—C47—C46 | −153.14 (14) |
| C9—N3—C16—N4 | −152.66 (12) | C40—N10—C47—N11 | −155.99 (12) |
| B1—N3—C16—N4 | 16.80 (19) | B2—N10—C47—N11 | 14.58 (19) |
| C9—N3—C16—C15 | 12.70 (14) | C40—N10—C47—C46 | 10.44 (15) |
| B1—N3—C16—C15 | −177.84 (11) | B2—N10—C47—C46 | −178.98 (11) |
| C14—C15—C16—N4 | −19.1 (2) | C45—C46—C47—N11 | −15.7 (2) |
| C10—C15—C16—N4 | 155.57 (13) | C41—C46—C47—N11 | 158.82 (13) |
| C14—C15—C16—N3 | 177.09 (14) | C45—C46—C47—N10 | 179.22 (14) |
| C10—C15—C16—N3 | −8.24 (14) | C41—C46—C47—N10 | −6.25 (14) |
| C16—N4—C17—N5 | −8.54 (19) | C47—N11—C48—N12 | −8.67 (18) |
| C16—N4—C17—C18 | 156.14 (13) | C47—N11—C48—C49 | 155.79 (13) |
| C24—N5—C17—N4 | 156.40 (12) | C55—N12—C48—N11 | 153.61 (12) |
| B1—N5—C17—N4 | −12.61 (19) | B2—N12—C48—N11 | −16.58 (19) |
| C24—N5—C17—C18 | −11.60 (15) | C55—N12—C48—C49 | −14.09 (14) |
| B1—N5—C17—C18 | 179.39 (11) | B2—N12—C48—C49 | 175.73 (11) |
| N4—C17—C18—C19 | 17.0 (3) | N11—C48—C49—C50 | 20.8 (2) |
| N5—C17—C18—C19 | −176.36 (15) | N12—C48—C49—C50 | −172.79 (14) |
| N4—C17—C18—C23 | −160.04 (14) | N11—C48—C49—C54 | −158.87 (13) |
| N5—C17—C18—C23 | 6.61 (14) | N12—C48—C49—C54 | 7.55 (14) |
| C23—C18—C19—C20 | −2.8 (2) | C54—C49—C50—C51 | −3.7 (2) |
| C17—C18—C19—C20 | −179.47 (14) | C48—C49—C50—C51 | 176.72 (14) |
| C18—C19—C20—C21 | 2.3 (2) | C49—C50—C51—C52 | 2.3 (2) |
| C19—C20—C21—C22 | 0.3 (2) | C50—C51—C52—C53 | 1.4 (2) |
| C20—C21—C22—C23 | −2.5 (2) | C51—C52—C53—C54 | −3.6 (2) |
| C21—C22—C23—C18 | 2.1 (2) | C52—C53—C54—C49 | 2.2 (2) |
| C21—C22—C23—C24 | 179.51 (14) | C52—C53—C54—C55 | −177.52 (14) |
| C19—C18—C23—C22 | 0.6 (2) | C50—C49—C54—C53 | 1.4 (2) |
| C17—C18—C23—C22 | 178.05 (12) | C48—C49—C54—C53 | −178.85 (12) |
| C19—C18—C23—C24 | −177.44 (12) | C50—C49—C54—C55 | −178.78 (12) |
| C17—C18—C23—C24 | 0.04 (14) | C48—C49—C54—C55 | 0.92 (15) |
| C1—N6—C24—N5 | 9.36 (18) | C32—N13—C55—N12 | 5.74 (19) |
| C1—N6—C24—C23 | −155.11 (13) | C32—N13—C55—C54 | −159.42 (14) |
| C17—N5—C24—N6 | −156.04 (12) | C48—N12—C55—N13 | −153.71 (12) |
| B1—N5—C24—N6 | 13.13 (19) | B2—N12—C55—N13 | 16.2 (2) |
| C17—N5—C24—C23 | 11.64 (15) | C48—N12—C55—C54 | 14.63 (14) |
| B1—N5—C24—C23 | −179.19 (11) | B2—N12—C55—C54 | −175.46 (12) |
| C22—C23—C24—N6 | −17.9 (2) | C53—C54—C55—N13 | −22.3 (3) |
| C18—C23—C24—N6 | 159.82 (13) | C49—C54—C55—N13 | 158.00 (14) |
| C22—C23—C24—N5 | 175.58 (14) | C53—C54—C55—N12 | 170.69 (14) |
| C18—C23—C24—N5 | −6.70 (14) | C49—C54—C55—N12 | −9.04 (14) |
| C31—N7—C25—C26 | −23.22 (18) | C62—N14—C56—C61 | 160.96 (13) |
| B1—N7—C25—C26 | 116.85 (15) | B2—N14—C56—C61 | −23.3 (2) |
| C31—N7—C25—C30 | 154.75 (13) | C62—N14—C56—C57 | −17.44 (19) |
| B1—N7—C25—C30 | −65.19 (18) | B2—N14—C56—C57 | 158.30 (13) |
| C30—C25—C26—C27 | 0.4 (2) | C61—C56—C57—C58 | 1.1 (2) |
| N7—C25—C26—C27 | 178.44 (13) | N14—C56—C57—C58 | 179.60 (14) |
| C25—C26—C27—C28 | 1.4 (2) | C56—C57—C58—C59 | 0.2 (3) |
| C26—C27—C28—C29 | −1.1 (3) | C57—C58—C59—C60 | −0.7 (3) |
| C27—C28—C29—C30 | −0.9 (3) | C58—C59—C60—C61 | −0.1 (2) |
| C28—C29—C30—C25 | 2.7 (2) | C59—C60—C61—C56 | 1.5 (2) |
| C26—C25—C30—C29 | −2.4 (2) | N14—C56—C61—C60 | 179.57 (13) |
| N7—C25—C30—C29 | 179.54 (14) | C57—C56—C61—C60 | −1.9 (2) |
| C8—N1—B1—N5 | −136.81 (12) | C47—N10—B2—N14 | 92.61 (15) |
| C1—N1—B1—N5 | 35.30 (16) | C40—N10—B2—N14 | −97.83 (14) |
| C8—N1—B1—N7 | 96.56 (15) | C47—N10—B2—N12 | −33.31 (16) |
| C1—N1—B1—N7 | −91.33 (15) | C40—N10—B2—N12 | 136.26 (12) |
| C8—N1—B1—N3 | −30.44 (16) | C47—N10—B2—N8 | −138.06 (12) |
| C1—N1—B1—N3 | 141.67 (11) | C40—N10—B2—N8 | 31.51 (16) |
| C24—N5—B1—N1 | −32.34 (16) | C56—N14—B2—N10 | −164.96 (12) |
| C17—N5—B1—N1 | 135.72 (12) | C62—N14—B2—N10 | 10.56 (18) |
| C24—N5—B1—N7 | 91.99 (15) | C56—N14—B2—N12 | −47.17 (18) |
| C17—N5—B1—N7 | −99.96 (15) | C62—N14—B2—N12 | 128.35 (14) |
| C24—N5—B1—N3 | −138.32 (12) | C56—N14—B2—N8 | 75.00 (17) |
| C17—N5—B1—N3 | 29.73 (16) | C62—N14—B2—N8 | −109.48 (15) |
| C25—N7—B1—N1 | 171.31 (11) | C48—N12—B2—N10 | 34.20 (15) |
| C31—N7—B1—N1 | −48.35 (16) | C55—N12—B2—N10 | −134.76 (12) |
| C25—N7—B1—N5 | 52.36 (17) | C48—N12—B2—N14 | −89.21 (15) |
| C31—N7—B1—N5 | −167.30 (12) | C55—N12—B2—N14 | 101.83 (15) |
| C25—N7—B1—N3 | −70.06 (16) | C48—N12—B2—N8 | 139.70 (12) |
| C31—N7—B1—N3 | 70.28 (15) | C55—N12—B2—N8 | −29.26 (16) |
| C9—N3—B1—N1 | 30.12 (16) | C32—N8—B2—N10 | 132.17 (13) |
| C16—N3—B1—N1 | −138.18 (12) | C39—N8—B2—N10 | −32.85 (16) |
| C9—N3—B1—N5 | 136.56 (12) | C32—N8—B2—N14 | −102.64 (15) |
| C16—N3—B1—N5 | −31.74 (16) | C39—N8—B2—N14 | 92.34 (16) |
| C9—N3—B1—N7 | −94.14 (15) | C32—N8—B2—N12 | 26.77 (17) |
| C16—N3—B1—N7 | 97.56 (15) | C39—N8—B2—N12 | −138.24 (12) |
(N-Phenylbenzamido)(subphthalocyaninato)boron (d22150_a) top
Crystal data top
| C31H20BN7 | F(000) = 1040 |
| Mr = 501.35 | Dx = 1.390 Mg m−3 |
| Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
| a = 10.3502 (4) Å | Cell parameters from 9219 reflections |
| b = 20.7509 (8) Å | θ = 4.3–65.8° |
| c = 12.2816 (5) Å | µ = 0.68 mm−1 |
| β = 114.734 (2)° | T = 150 K |
| V = 2395.80 (17) Å3 | Shard, purple |
| Z = 4 | 0.19 × 0.14 × 0.09 mm |
Data collection top
| Bruker Kappa APEX-DUO CMOS PHOTON II diffractometer | 3432 reflections with I > 2σ(I) |
| Radiation source: Inoatec ImuS with multi-layer optics | Rint = 0.111 |
| φ and ω scans | θmax = 66.4°, θmin = 4.3° |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −12→12 |
| Tmin = 0.462, Tmax = 0.753 | k = −24→24 |
| 41606 measured reflections | l = −14→14 |
| 4159 independent reflections |
Refinement top
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.055 | w = 1/[σ2(Fo2) + (0.1179P)2] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.165 | (Δ/σ)max < 0.001 |
| S = 1.06 | Δρmax = 0.28 e Å−3 |
| 4159 reflections | Δρmin = −0.35 e Å−3 |
| 354 parameters | Extinction correction: SHELXL2019 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| 0 restraints | Extinction coefficient: 0.0101 (12) |
| Primary atom site location: structure-invariant direct methods |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| N1 | 0.65532 (16) | 0.59175 (7) | 0.21413 (13) | 0.0257 (4) | |
| N2 | 0.73697 (17) | 0.69317 (7) | 0.17604 (13) | 0.0281 (4) | |
| N3 | 0.75068 (16) | 0.66827 (7) | 0.36934 (13) | 0.0258 (4) | |
| N4 | 0.87250 (17) | 0.63159 (8) | 0.57049 (13) | 0.0286 (4) | |
| N5 | 0.73686 (17) | 0.55959 (7) | 0.41500 (13) | 0.0268 (4) | |
| N6 | 0.69933 (16) | 0.48035 (7) | 0.26647 (13) | 0.0287 (4) | |
| N7 | 0.50830 (17) | 0.62224 (7) | 0.33581 (14) | 0.0295 (4) | |
| B1 | 0.6507 (2) | 0.61169 (10) | 0.33133 (18) | 0.0260 (5) | |
| C1 | 0.66648 (19) | 0.52872 (9) | 0.18618 (16) | 0.0274 (4) | |
| C2 | 0.67281 (19) | 0.52945 (9) | 0.07061 (16) | 0.0279 (5) | |
| C3 | 0.6813 (2) | 0.48015 (10) | −0.00334 (17) | 0.0326 (5) | |
| H3A | 0.675160 | 0.436222 | 0.015789 | 0.039* | |
| C4 | 0.6988 (2) | 0.49697 (11) | −0.10515 (18) | 0.0385 (5) | |
| H4A | 0.704486 | 0.464057 | −0.156727 | 0.046* | |
| C5 | 0.7083 (2) | 0.56135 (11) | −0.13372 (18) | 0.0399 (5) | |
| H5A | 0.719779 | 0.571278 | −0.204686 | 0.048* | |
| C6 | 0.7015 (2) | 0.61122 (10) | −0.06111 (16) | 0.0335 (5) | |
| H6A | 0.709225 | 0.654920 | −0.080673 | 0.040* | |
| C7 | 0.68294 (19) | 0.59499 (10) | 0.04165 (16) | 0.0291 (5) | |
| C8 | 0.68407 (19) | 0.63353 (9) | 0.14095 (16) | 0.0271 (4) | |
| C9 | 0.7765 (2) | 0.70803 (9) | 0.29241 (16) | 0.0259 (4) | |
| C10 | 0.8777 (2) | 0.75606 (9) | 0.36766 (16) | 0.0268 (4) | |
| C11 | 0.9404 (2) | 0.80922 (9) | 0.34031 (17) | 0.0297 (5) | |
| H11A | 0.914763 | 0.821832 | 0.259550 | 0.036* | |
| C12 | 1.0412 (2) | 0.84310 (9) | 0.43435 (18) | 0.0340 (5) | |
| H12A | 1.082772 | 0.880434 | 0.417544 | 0.041* | |
| C13 | 1.0837 (2) | 0.82399 (10) | 0.55379 (19) | 0.0345 (5) | |
| H13A | 1.154291 | 0.848103 | 0.616179 | 0.041* | |
| C14 | 1.0241 (2) | 0.77033 (9) | 0.58198 (18) | 0.0308 (5) | |
| H14A | 1.054145 | 0.756741 | 0.662766 | 0.037* | |
| C15 | 0.9192 (2) | 0.73697 (9) | 0.48870 (16) | 0.0274 (4) | |
| C16 | 0.8426 (2) | 0.67775 (9) | 0.48600 (16) | 0.0266 (4) | |
| C17 | 0.8247 (2) | 0.57179 (9) | 0.53119 (16) | 0.0274 (5) | |
| C18 | 0.8719 (2) | 0.50927 (9) | 0.58638 (16) | 0.0285 (4) | |
| C19 | 0.9529 (2) | 0.49073 (10) | 0.70445 (17) | 0.0315 (5) | |
| H19A | 0.989752 | 0.521786 | 0.766778 | 0.038* | |
| C20 | 0.9779 (2) | 0.42583 (10) | 0.72813 (18) | 0.0340 (5) | |
| H20A | 1.029217 | 0.411922 | 0.808573 | 0.041* | |
| C21 | 0.9292 (2) | 0.38011 (10) | 0.63620 (18) | 0.0331 (5) | |
| H21A | 0.948039 | 0.335780 | 0.655653 | 0.040* | |
| C22 | 0.8544 (2) | 0.39775 (9) | 0.51793 (19) | 0.0317 (5) | |
| H22A | 0.826125 | 0.366534 | 0.455678 | 0.038* | |
| C23 | 0.8217 (2) | 0.46271 (9) | 0.49248 (17) | 0.0279 (4) | |
| C24 | 0.7415 (2) | 0.49745 (9) | 0.38169 (16) | 0.0277 (4) | |
| C25 | 0.4518 (2) | 0.68471 (9) | 0.32846 (17) | 0.0298 (5) | |
| C26 | 0.4561 (2) | 0.72829 (10) | 0.24303 (18) | 0.0338 (5) | |
| H26A | 0.493158 | 0.714706 | 0.187913 | 0.041* | |
| C27 | 0.4072 (2) | 0.79084 (11) | 0.2374 (2) | 0.0413 (5) | |
| H27A | 0.414424 | 0.820032 | 0.180682 | 0.050* | |
| C28 | 0.3480 (2) | 0.81124 (11) | 0.3135 (2) | 0.0452 (6) | |
| H28A | 0.313590 | 0.854061 | 0.308949 | 0.054* | |
| C29 | 0.3396 (2) | 0.76848 (12) | 0.3959 (2) | 0.0454 (6) | |
| H29A | 0.297853 | 0.781872 | 0.447959 | 0.054* | |
| C30 | 0.3913 (2) | 0.70597 (10) | 0.40425 (19) | 0.0366 (5) | |
| H30A | 0.385245 | 0.677382 | 0.462364 | 0.044* | |
| C31 | 0.4606 (2) | 0.57447 (10) | 0.3988 (2) | 0.0382 (5) | |
| H31A | 0.487879 | 0.531267 | 0.383831 | 0.057* | |
| H31B | 0.356914 | 0.576775 | 0.369558 | 0.057* | |
| H31C | 0.505052 | 0.583395 | 0.485013 | 0.057* |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N1 | 0.0278 (8) | 0.0275 (9) | 0.0265 (8) | −0.0002 (6) | 0.0159 (6) | −0.0006 (6) |
| N2 | 0.0313 (9) | 0.0293 (9) | 0.0274 (8) | 0.0018 (7) | 0.0159 (7) | 0.0015 (6) |
| N3 | 0.0302 (8) | 0.0260 (8) | 0.0266 (8) | 0.0006 (6) | 0.0172 (7) | 0.0000 (6) |
| N4 | 0.0369 (9) | 0.0273 (9) | 0.0279 (8) | 0.0006 (7) | 0.0200 (7) | −0.0001 (6) |
| N5 | 0.0302 (9) | 0.0269 (9) | 0.0282 (8) | −0.0002 (6) | 0.0169 (7) | −0.0006 (6) |
| N6 | 0.0292 (8) | 0.0303 (9) | 0.0303 (9) | −0.0018 (7) | 0.0162 (7) | −0.0015 (7) |
| N7 | 0.0337 (9) | 0.0274 (9) | 0.0358 (9) | 0.0006 (7) | 0.0228 (7) | 0.0013 (6) |
| B1 | 0.0293 (11) | 0.0270 (11) | 0.0256 (11) | 0.0007 (9) | 0.0154 (9) | 0.0011 (8) |
| C1 | 0.0261 (10) | 0.0299 (10) | 0.0290 (9) | −0.0022 (8) | 0.0144 (8) | −0.0036 (8) |
| C2 | 0.0237 (10) | 0.0348 (11) | 0.0275 (9) | −0.0012 (8) | 0.0129 (8) | −0.0027 (8) |
| C3 | 0.0283 (10) | 0.0368 (11) | 0.0321 (10) | 0.0004 (8) | 0.0120 (8) | −0.0066 (8) |
| C4 | 0.0380 (12) | 0.0453 (13) | 0.0368 (11) | −0.0008 (10) | 0.0203 (9) | −0.0099 (9) |
| C5 | 0.0437 (13) | 0.0520 (14) | 0.0300 (11) | −0.0046 (10) | 0.0214 (9) | −0.0048 (9) |
| C6 | 0.0361 (11) | 0.0412 (12) | 0.0267 (10) | −0.0040 (9) | 0.0167 (8) | −0.0024 (8) |
| C7 | 0.0254 (10) | 0.0362 (11) | 0.0279 (10) | −0.0015 (8) | 0.0134 (8) | −0.0020 (8) |
| C8 | 0.0269 (10) | 0.0328 (11) | 0.0250 (9) | 0.0014 (8) | 0.0142 (8) | 0.0014 (7) |
| C9 | 0.0293 (10) | 0.0270 (10) | 0.0266 (9) | 0.0039 (8) | 0.0168 (8) | 0.0027 (7) |
| C10 | 0.0329 (10) | 0.0247 (10) | 0.0305 (10) | 0.0032 (8) | 0.0207 (8) | −0.0011 (7) |
| C11 | 0.0356 (11) | 0.0277 (11) | 0.0339 (10) | 0.0042 (8) | 0.0227 (9) | 0.0025 (8) |
| C12 | 0.0387 (11) | 0.0271 (10) | 0.0447 (12) | −0.0021 (8) | 0.0259 (9) | −0.0011 (8) |
| C13 | 0.0371 (11) | 0.0307 (11) | 0.0398 (11) | −0.0028 (8) | 0.0201 (9) | −0.0063 (8) |
| C14 | 0.0375 (11) | 0.0278 (10) | 0.0311 (10) | 0.0021 (8) | 0.0184 (9) | −0.0020 (8) |
| C15 | 0.0353 (10) | 0.0242 (10) | 0.0307 (10) | 0.0025 (8) | 0.0217 (8) | −0.0016 (7) |
| C16 | 0.0312 (10) | 0.0275 (10) | 0.0276 (10) | −0.0003 (8) | 0.0186 (8) | −0.0016 (7) |
| C17 | 0.0329 (10) | 0.0291 (10) | 0.0259 (10) | 0.0005 (8) | 0.0179 (8) | 0.0005 (7) |
| C18 | 0.0315 (10) | 0.0280 (10) | 0.0324 (10) | −0.0001 (8) | 0.0199 (8) | 0.0027 (8) |
| C19 | 0.0312 (10) | 0.0364 (11) | 0.0316 (10) | −0.0020 (8) | 0.0178 (8) | 0.0030 (8) |
| C20 | 0.0290 (11) | 0.0374 (12) | 0.0379 (11) | 0.0040 (8) | 0.0161 (9) | 0.0095 (9) |
| C21 | 0.0299 (11) | 0.0307 (11) | 0.0455 (12) | 0.0045 (8) | 0.0223 (9) | 0.0092 (9) |
| C22 | 0.0306 (10) | 0.0287 (11) | 0.0449 (12) | 0.0006 (8) | 0.0248 (9) | 0.0010 (8) |
| C23 | 0.0264 (10) | 0.0304 (11) | 0.0341 (10) | 0.0006 (8) | 0.0198 (8) | 0.0034 (8) |
| C24 | 0.0304 (10) | 0.0266 (10) | 0.0332 (10) | −0.0001 (8) | 0.0203 (8) | −0.0003 (8) |
| C25 | 0.0278 (10) | 0.0318 (11) | 0.0320 (10) | −0.0010 (8) | 0.0146 (8) | −0.0019 (8) |
| C26 | 0.0309 (10) | 0.0387 (12) | 0.0343 (11) | 0.0033 (9) | 0.0163 (8) | 0.0042 (8) |
| C27 | 0.0389 (12) | 0.0407 (13) | 0.0450 (13) | 0.0040 (9) | 0.0182 (10) | 0.0096 (10) |
| C28 | 0.0449 (13) | 0.0367 (12) | 0.0522 (14) | 0.0098 (10) | 0.0184 (11) | −0.0012 (10) |
| C29 | 0.0458 (13) | 0.0500 (14) | 0.0466 (13) | 0.0096 (11) | 0.0256 (11) | −0.0068 (10) |
| C30 | 0.0402 (12) | 0.0396 (12) | 0.0365 (11) | 0.0038 (9) | 0.0226 (9) | −0.0007 (9) |
| C31 | 0.0401 (12) | 0.0386 (12) | 0.0470 (13) | −0.0024 (9) | 0.0293 (10) | 0.0044 (9) |
Geometric parameters (Å, º) top
| N1—C8 | 1.368 (2) | C11—H11A | 0.9500 |
| N1—C1 | 1.369 (2) | C12—C13 | 1.401 (3) |
| N1—B1 | 1.518 (2) | C12—H12A | 0.9500 |
| N2—C9 | 1.348 (2) | C13—C14 | 1.385 (3) |
| N2—C8 | 1.349 (3) | C13—H13A | 0.9500 |
| N3—C16 | 1.362 (2) | C14—C15 | 1.389 (3) |
| N3—C9 | 1.362 (2) | C14—H14A | 0.9500 |
| N3—B1 | 1.504 (3) | C15—C16 | 1.456 (3) |
| N4—C17 | 1.348 (2) | C17—C18 | 1.450 (3) |
| N4—C16 | 1.350 (2) | C18—C19 | 1.392 (3) |
| N5—C17 | 1.357 (2) | C18—C23 | 1.425 (3) |
| N5—C24 | 1.360 (2) | C19—C20 | 1.379 (3) |
| N5—B1 | 1.501 (3) | C19—H19A | 0.9500 |
| N6—C24 | 1.342 (2) | C20—C21 | 1.397 (3) |
| N6—C1 | 1.347 (2) | C20—H20A | 0.9500 |
| N7—C25 | 1.409 (3) | C21—C22 | 1.379 (3) |
| N7—C31 | 1.464 (3) | C21—H21A | 0.9500 |
| N7—B1 | 1.513 (3) | C22—C23 | 1.393 (3) |
| C1—C2 | 1.448 (3) | C22—H22A | 0.9500 |
| C2—C3 | 1.395 (3) | C23—C24 | 1.454 (3) |
| C2—C7 | 1.421 (3) | C25—C30 | 1.394 (3) |
| C3—C4 | 1.381 (3) | C25—C26 | 1.400 (3) |
| C3—H3A | 0.9500 | C26—C27 | 1.384 (3) |
| C4—C5 | 1.395 (3) | C26—H26A | 0.9500 |
| C4—H4A | 0.9500 | C27—C28 | 1.380 (3) |
| C5—C6 | 1.387 (3) | C27—H27A | 0.9500 |
| C5—H5A | 0.9500 | C28—C29 | 1.376 (3) |
| C6—C7 | 1.395 (3) | C28—H28A | 0.9500 |
| C6—H6A | 0.9500 | C29—C30 | 1.391 (3) |
| C7—C8 | 1.454 (3) | C29—H29A | 0.9500 |
| C9—C10 | 1.461 (3) | C30—H30A | 0.9500 |
| C10—C11 | 1.390 (3) | C31—H31A | 0.9800 |
| C10—C15 | 1.420 (3) | C31—H31B | 0.9800 |
| C11—C12 | 1.381 (3) | C31—H31C | 0.9800 |
| C8—N1—C1 | 112.10 (15) | C12—C13—H13A | 119.6 |
| C8—N1—B1 | 123.51 (16) | C13—C14—C15 | 118.07 (18) |
| C1—N1—B1 | 122.53 (15) | C13—C14—H14A | 121.0 |
| C9—N2—C8 | 116.83 (15) | C15—C14—H14A | 121.0 |
| C16—N3—C9 | 112.88 (15) | C14—C15—C10 | 120.93 (17) |
| C16—N3—B1 | 121.73 (15) | C14—C15—C16 | 132.07 (17) |
| C9—N3—B1 | 124.51 (15) | C10—C15—C16 | 106.76 (15) |
| C17—N4—C16 | 116.49 (16) | N4—C16—N3 | 122.75 (17) |
| C17—N5—C24 | 113.64 (15) | N4—C16—C15 | 129.35 (17) |
| C17—N5—B1 | 122.02 (15) | N3—C16—C15 | 106.25 (15) |
| C24—N5—B1 | 124.24 (15) | N4—C17—N5 | 122.15 (17) |
| C24—N6—C1 | 116.48 (16) | N4—C17—C18 | 130.88 (17) |
| C25—N7—C31 | 115.73 (16) | N5—C17—C18 | 105.73 (16) |
| C25—N7—B1 | 120.98 (15) | C19—C18—C23 | 120.82 (18) |
| C31—N7—B1 | 118.03 (15) | C19—C18—C17 | 132.26 (18) |
| N5—B1—N3 | 102.41 (15) | C23—C18—C17 | 106.90 (16) |
| N5—B1—N7 | 112.84 (16) | C20—C19—C18 | 117.89 (19) |
| N3—B1—N7 | 115.47 (16) | C20—C19—H19A | 121.1 |
| N5—B1—N1 | 101.96 (15) | C18—C19—H19A | 121.1 |
| N3—B1—N1 | 102.49 (15) | C19—C20—C21 | 121.34 (19) |
| N7—B1—N1 | 119.45 (16) | C19—C20—H20A | 119.3 |
| N6—C1—N1 | 123.37 (16) | C21—C20—H20A | 119.3 |
| N6—C1—C2 | 128.62 (17) | C22—C21—C20 | 121.64 (19) |
| N1—C1—C2 | 106.19 (15) | C22—C21—H21A | 119.2 |
| C3—C2—C7 | 120.52 (18) | C20—C21—H21A | 119.2 |
| C3—C2—C1 | 132.17 (18) | C21—C22—C23 | 118.01 (19) |
| C7—C2—C1 | 107.09 (16) | C21—C22—H22A | 121.0 |
| C4—C3—C2 | 118.15 (19) | C23—C22—H22A | 121.0 |
| C4—C3—H3A | 120.9 | C22—C23—C18 | 120.14 (17) |
| C2—C3—H3A | 120.9 | C22—C23—C24 | 132.81 (18) |
| C3—C4—C5 | 121.31 (19) | C18—C23—C24 | 107.04 (16) |
| C3—C4—H4A | 119.3 | N6—C24—N5 | 122.07 (16) |
| C5—C4—H4A | 119.3 | N6—C24—C23 | 131.43 (17) |
| C6—C5—C4 | 121.65 (19) | N5—C24—C23 | 105.47 (15) |
| C6—C5—H5A | 119.2 | C30—C25—C26 | 117.39 (18) |
| C4—C5—H5A | 119.2 | C30—C25—N7 | 122.60 (18) |
| C5—C6—C7 | 117.7 (2) | C26—C25—N7 | 120.01 (17) |
| C5—C6—H6A | 121.1 | C27—C26—C25 | 121.2 (2) |
| C7—C6—H6A | 121.1 | C27—C26—H26A | 119.4 |
| C6—C7—C2 | 120.67 (18) | C25—C26—H26A | 119.4 |
| C6—C7—C8 | 132.07 (19) | C28—C27—C26 | 120.7 (2) |
| C2—C7—C8 | 106.98 (16) | C28—C27—H27A | 119.6 |
| N2—C8—N1 | 122.84 (16) | C26—C27—H27A | 119.6 |
| N2—C8—C7 | 129.21 (17) | C29—C28—C27 | 118.9 (2) |
| N1—C8—C7 | 105.95 (16) | C29—C28—H28A | 120.6 |
| N2—C9—N3 | 122.43 (17) | C27—C28—H28A | 120.6 |
| N2—C9—C10 | 130.26 (16) | C28—C29—C30 | 121.0 (2) |
| N3—C9—C10 | 105.73 (15) | C28—C29—H29A | 119.5 |
| C11—C10—C15 | 120.45 (17) | C30—C29—H29A | 119.5 |
| C11—C10—C9 | 132.22 (17) | C29—C30—C25 | 120.9 (2) |
| C15—C10—C9 | 107.14 (15) | C29—C30—H30A | 119.6 |
| C12—C11—C10 | 117.86 (18) | C25—C30—H30A | 119.6 |
| C12—C11—H11A | 121.1 | N7—C31—H31A | 109.5 |
| C10—C11—H11A | 121.1 | N7—C31—H31B | 109.5 |
| C11—C12—C13 | 121.87 (19) | H31A—C31—H31B | 109.5 |
| C11—C12—H12A | 119.1 | N7—C31—H31C | 109.5 |
| C13—C12—H12A | 119.1 | H31A—C31—H31C | 109.5 |
| C14—C13—C12 | 120.76 (19) | H31B—C31—H31C | 109.5 |
| C14—C13—H13A | 119.6 | ||
| C17—N5—B1—N3 | 37.5 (2) | C15—C10—C11—C12 | −1.3 (3) |
| C24—N5—B1—N3 | −138.68 (17) | C9—C10—C11—C12 | −175.58 (19) |
| C17—N5—B1—N7 | −87.3 (2) | C10—C11—C12—C13 | 2.1 (3) |
| C24—N5—B1—N7 | 96.5 (2) | C11—C12—C13—C14 | −0.9 (3) |
| C17—N5—B1—N1 | 143.34 (16) | C12—C13—C14—C15 | −1.3 (3) |
| C24—N5—B1—N1 | −32.8 (2) | C13—C14—C15—C10 | 2.1 (3) |
| C16—N3—B1—N5 | −34.8 (2) | C13—C14—C15—C16 | 175.63 (19) |
| C9—N3—B1—N5 | 133.72 (17) | C11—C10—C15—C14 | −0.8 (3) |
| C16—N3—B1—N7 | 88.3 (2) | C9—C10—C15—C14 | 174.77 (17) |
| C9—N3—B1—N7 | −103.3 (2) | C11—C10—C15—C16 | −175.80 (17) |
| C16—N3—B1—N1 | −140.19 (16) | C9—C10—C15—C16 | −0.24 (19) |
| C9—N3—B1—N1 | 28.3 (2) | C17—N4—C16—N3 | 10.2 (3) |
| C25—N7—B1—N5 | 141.49 (17) | C17—N4—C16—C15 | −153.12 (19) |
| C31—N7—B1—N5 | −11.8 (2) | C9—N3—C16—N4 | −155.34 (17) |
| C25—N7—B1—N3 | 24.2 (2) | B1—N3—C16—N4 | 14.4 (3) |
| C31—N7—B1—N3 | −129.11 (18) | C9—N3—C16—C15 | 11.3 (2) |
| C25—N7—B1—N1 | −98.8 (2) | B1—N3—C16—C15 | −179.02 (16) |
| C31—N7—B1—N1 | 107.9 (2) | C14—C15—C16—N4 | −15.1 (3) |
| C8—N1—B1—N5 | −133.49 (17) | C10—C15—C16—N4 | 159.09 (19) |
| C1—N1—B1—N5 | 29.8 (2) | C14—C15—C16—N3 | 179.45 (19) |
| C8—N1—B1—N3 | −27.7 (2) | C10—C15—C16—N3 | −6.32 (19) |
| C1—N1—B1—N3 | 135.54 (16) | C16—N4—C17—N5 | −7.6 (3) |
| C8—N1—B1—N7 | 101.4 (2) | C16—N4—C17—C18 | 157.72 (19) |
| C1—N1—B1—N7 | −95.3 (2) | C24—N5—C17—N4 | 156.89 (18) |
| C24—N6—C1—N1 | −9.3 (3) | B1—N5—C17—N4 | −19.7 (3) |
| C24—N6—C1—C2 | 153.20 (19) | C24—N5—C17—C18 | −11.6 (2) |
| C8—N1—C1—N6 | 152.83 (17) | B1—N5—C17—C18 | 171.81 (17) |
| B1—N1—C1—N6 | −12.1 (3) | N4—C17—C18—C19 | 18.9 (4) |
| C8—N1—C1—C2 | −13.0 (2) | N5—C17—C18—C19 | −174.0 (2) |
| B1—N1—C1—C2 | −177.97 (15) | N4—C17—C18—C23 | −159.61 (19) |
| N6—C1—C2—C3 | 16.8 (3) | N5—C17—C18—C23 | 7.5 (2) |
| N1—C1—C2—C3 | −178.39 (19) | C23—C18—C19—C20 | −2.6 (3) |
| N6—C1—C2—C7 | −157.64 (18) | C17—C18—C19—C20 | 179.1 (2) |
| N1—C1—C2—C7 | 7.2 (2) | C18—C19—C20—C21 | 2.8 (3) |
| C7—C2—C3—C4 | −0.4 (3) | C19—C20—C21—C22 | 0.2 (3) |
| C1—C2—C3—C4 | −174.19 (19) | C20—C21—C22—C23 | −3.3 (3) |
| C2—C3—C4—C5 | 0.2 (3) | C21—C22—C23—C18 | 3.5 (3) |
| C3—C4—C5—C6 | 0.4 (3) | C21—C22—C23—C24 | −177.12 (19) |
| C4—C5—C6—C7 | −0.8 (3) | C19—C18—C23—C22 | −0.6 (3) |
| C5—C6—C7—C2 | 0.6 (3) | C17—C18—C23—C22 | 178.12 (17) |
| C5—C6—C7—C8 | 173.7 (2) | C19—C18—C23—C24 | 179.91 (17) |
| C3—C2—C7—C6 | 0.0 (3) | C17—C18—C23—C24 | −1.4 (2) |
| C1—C2—C7—C6 | 175.20 (17) | C1—N6—C24—N5 | 6.9 (3) |
| C3—C2—C7—C8 | −174.65 (16) | C1—N6—C24—C23 | −159.73 (19) |
| C1—C2—C7—C8 | 0.6 (2) | C17—N5—C24—N6 | −158.89 (17) |
| C9—N2—C8—N1 | 7.4 (3) | B1—N5—C24—N6 | 17.6 (3) |
| C9—N2—C8—C7 | −154.15 (19) | C17—N5—C24—C23 | 10.7 (2) |
| C1—N1—C8—N2 | −151.92 (17) | B1—N5—C24—C23 | −172.81 (17) |
| B1—N1—C8—N2 | 12.9 (3) | C22—C23—C24—N6 | −16.4 (4) |
| C1—N1—C8—C7 | 13.3 (2) | C18—C23—C24—N6 | 163.04 (19) |
| B1—N1—C8—C7 | 178.11 (16) | C22—C23—C24—N5 | 175.3 (2) |
| C6—C7—C8—N2 | −17.9 (3) | C18—C23—C24—N5 | −5.2 (2) |
| C2—C7—C8—N2 | 155.87 (18) | C31—N7—C25—C30 | 19.0 (3) |
| C6—C7—C8—N1 | 178.1 (2) | B1—N7—C25—C30 | −134.9 (2) |
| C2—C7—C8—N1 | −8.09 (19) | C31—N7—C25—C26 | −161.42 (18) |
| C8—N2—C9—N3 | −7.2 (3) | B1—N7—C25—C26 | 44.7 (3) |
| C8—N2—C9—C10 | 156.40 (18) | C30—C25—C26—C27 | 2.5 (3) |
| C16—N3—C9—N2 | 155.68 (17) | N7—C25—C26—C27 | −177.08 (19) |
| B1—N3—C9—N2 | −13.7 (3) | C25—C26—C27—C28 | −2.4 (3) |
| C16—N3—C9—C10 | −11.4 (2) | C26—C27—C28—C29 | 0.6 (3) |
| B1—N3—C9—C10 | 179.27 (16) | C27—C28—C29—C30 | 0.8 (4) |
| N2—C9—C10—C11 | 15.9 (3) | C28—C29—C30—C25 | −0.6 (3) |
| N3—C9—C10—C11 | −178.48 (19) | C26—C25—C30—C29 | −1.1 (3) |
| N2—C9—C10—C15 | −158.94 (19) | N7—C25—C30—C29 | 178.54 (19) |
| N3—C9—C10—C15 | 6.70 (19) |
Summary of π–π interactions (Å), not including any axial group interactions top
| Axial group | Concave–concave | Convex–convex | Concave–convex | ||||
| Head-to-head' | Head-to-tail | Head-to-head | Head-to-tail | Tail-to-tail | Head-to-head | Head-to-tail | |
| Cl (1) | - | 4.150 | 3.615a | - | - | - | - |
| Br (2) | - | 4.151 | 3.661a | - | - | - | - |
| MeO (3) | - | 4.044 | - | - | - | - | - |
| EtO (4-I) | 3.574a | - | - | - | - | - | - |
| EtO (4-II) | 3.577a | - | - | - | - | - | - |
| F3EtO (5) | 3.640a | - | - | 3.822 | - | - | - |
| ButO (6) | 3.612a | - | - | 4.295 | - | - | - |
| tButO (7) | 3.564a | - | - | - | - | - | - |
| OctO (8) | - | - | - | - | - | 3.628a, 3.673a | 3.890 |
| PhO (9) | 3.674a | - | - | - | - | - | - |
| Naphthoxy (10) | - | - | - | - | - | - | - |
| Acetate (11) | 3.620a | - | - | - | 3.897 | - | - |
| Benzoate (12) | - | - | - | 4.163 | - | - | - |
| TMSO (13) | 3.543a | - | - | - | - | - | - |
| F5PhS (14) | - | - | - | - | - | - | 3.958 |
| MePhS (15) | 3.659a | 4.040 | 3.577a | ||||
| 3.691a | |||||||
| 3.537b | |||||||
| 3.861a | |||||||
| 3.934a | |||||||
| 3.911b' | |||||||
| PhMeN (16-I) | 3.705a | - | - | - | - | - | - |
| PhMeN (16-II) | 3.790a | - | - | - | - | - | - |
| Notes: (a) πpyr–πPh distance; (b) πPh–πPh distance. |
Summary of intermolecular interactions (Å) involving the axial group top
| Axial group | Convex-to-axial ligand | Concave-to-axial ligand | Hydrogen/halogen bonding | πax interactions | ||||||||
| B—A···πPh | C—Hax···πPh | πax···πtail | πax···πPh | C—Hax···πPh | B—A···HPh—C | C—Hax···Nimine | C—Fax···HPh—C | C═Oax···HPh—C | C—HPh···πax | B—A···πax | C—Hax···πax | |
| Cl (1) | 3.548 | - | - | - | - | 2.893b | - | - | - | - | - | - |
| Br (2) | 3.475 | - | - | - | - | 2.977b | - | - | - | - | - | - |
| MeO (3) | - | 2.605 | - | - | - | 2.637a | - | - | - | - | - | - |
| EtO (4-I) | - | - | - | - | 3.593 | 2.682a | - | - | - | - | - | - |
| EtO (4-II) | - | - | - | - | 3.590 | 2.690a | - | - | - | - | - | - |
| F3EtO (5) | - | - | - | - | - | 2.446a | 2.622a | 2.529a | - | - | - | - |
| ButO (6) | - | 3.319 | - | - | - | 2.556a | 2.640a | - | - | - | - | - |
| tButO (7) | - | 3.057 | - | - | - | - | - | - | - | - | - | - |
| OctO (8) | - | 2.971 | - | - | - | 2.641a | - | - | - | - | - | - |
| PhO (9) | - | - | - | - | - | - | - | - | - | - | - | - |
| Naphthoxy (10) | - | - | 3.813 | - | - | 2.627a | - | - | - | - | - | - |
| Acetate (11) | - | - | - | - | - | 2.581a | 2.635a | - | 2.628a | - | - | - |
| Benzoate (12) | - | - | - | - | - | - | - | - | 2.510a, 2.536a | 2.726, 3.612 | - | - |
| TMSO (13) | - | 3.070 | - | - | - | 2.478a | - | - | - | - | - | - |
| F5PhS (14) | - | - | - | 3.525 | - | - | - | 2.546a | - | - | 3.560 | - |
| MePhS (15) | 3.786 | - | 3.895 | - | - | - | - | - | - | - | - | 2.876 |
| PhMeN (16-I) | - | - | - | - | - | - | - | - | - | - | - | 3.048 |
| PhMeN (16-II) | - | 2.816 | - | - | - | - | - | - | - | - | - | - |
| Notes: (a) weak hydrogen bond; (b) halogen bond. |
Axial bond lengths (Å) and bowl depths (Å) of the investigated BsubPcs top
| Axial group | Axial bond length | Bowl depth to plane a | Bowl depth to plane b | Bowl depth to plane c |
| Cl (1) | 1.884 | 0.580 | 1.116 | 2.456 |
| Br (2) | 2.052 | 0.568 | 1.101 | 2.457 |
| MeO (3) | 1.424 | 0.632 | 1.191 | 2.618 |
| EtO (4-I) | 1.421 | 0.641 | 1.193 | 2.598 |
| EtO (4-II) | 1.418 | 0.642 | 1.192 | 2.590 |
| F3EtO (5) | 1.437 | 0.631 | 1.188 | 2.468 |
| ButO (6) | 1.417 | 0.643 | 1.210 | 2.718 |
| tButO (7) | 1.415 | 0.660 | 1.225 | 2.711 |
| OctO (8-A) | 1.416 | 0.643 | 1.230 | 2.867 |
| OctO (8-B) | 1.421 | 0.646 | 1.209 | 2.652 |
| OctO (8-C) | 1.406 | 0.640 | 1.195 | 2.493 |
| PhO (9) | 1.441 | 0.624 | 1.181 | 2.607 |
| Naphthoxy (10) | 1.441 | 0.620 | 1.202 | 2.881 |
| Acetate (11) | 1.473 | 0.603 | 1.158 | 2.389 |
| Benzoate (12) | 1.473 | 0.602 | 1.192 | 2.835 |
| TMSO (13) | 1.415 | 0.649 | 1.207 | 2.630 |
| F5PhS (14-A) | 1.955 | 0.587 | 1.183 | 2.751 |
| F5PhS (14-B) | 1.958 | 0.587 | 1.119 | 2.489 |
| MePhS (15-A) | 1.922 | 0.615 | 1.180 | 2.580 |
| MePhS (15-A) | 1.907 | 0.625 | 1.173 | 2.541 |
| MePhS (15-A) | 1.915 | 0.619 | 1.165 | 2.537 |
| PhMeN (16-1, mol 1) | 1.509 | 0.650 | 1.205 | 2.541 |
| PhMeN (16-1, mol 2) | 1.513 | 0.667 | 1.250 | 2.631 |
| PhMeN (16-2) | 1.513 | 0.659 | 1.217 | 2.595 |
Acknowledgements
This work was supported by Mitacs through the Mitacs Accelerate program that is present within Canada and a Hatch Graduate Scholarship from Hatch Ltd (Mississauga, Ontario, Canada). The authors also gratefully acknowledge the NSERC of Canada and their support of this work through a Discovery Grant (DG) to TPB.
Funding information
Funding for this research was provided by: Natural Sciences and Engineering Research Council of Canada.
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