Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229615019610/eg3191sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615019610/eg3191Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615019610/eg3191IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615019610/eg3191IIIsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615019610/eg3191IVsup5.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615019610/eg3191Isup6.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615019610/eg3191IIsup7.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615019610/eg3191IIIsup8.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615019610/eg3191IVsup9.cml |
CCDC references: 1431626; 1431625; 1431624; 1431623
\ Oxindole is the core structure in a variety of natural products and drugs. Oxindole derivatives (Klein & Taylor, 2011) have demonstrated significant potential for use in a wide range of biological applications such as NMDA antagonist (Kang et al., 2002), calcium channel blockers (Swensen et al., 2012) antiangiogenic (Whatmore et al., 2002), anticancer (Peddibhotla, 2009) and analgesic effects (Abbadie et al., 2010). The heterocyclic spirooxindole ring system is a recurring structural element that has been identified in numerous naturally occurring substances (Williams & Cox, 2003), characterized by highly pronounced biological properties, and pharmacologically active compounds. These spiro-fused ring systems display stereochemical and structural complexities that continue to challenge the synthetic chemist and as a consequence, a number of methods have been reported for the preparation of spirooxindole-fused heterocycles (Jadidi et al., 2009; Badillo et al., 2011; Esmaeili et al., 2011; Kiruthika et al., 2011). Isatin is probably one of the most commonly used reagents for constructing spirooxindoles in many reactions such as 1,3-dipolar cycloaddition, Morita–Baylis–Hillman reaction and other condensation reactions (Hong & Wang, 2013; Shi et al., 2012). Over the past few years, multicomponent reactions based on the versatile reactivity of isatins have emerged as efficient methods for the synthesis of various spirooxindoles (Basavaiah & Reddy, 2007; Cao et al., 2014). Reddy et al. (2015) reported a domino three-component synthesis of dispirooxindoles through [3+2] cycloaddition of carbonyl ylides with 3-arylideneoxindoles. In continuation of our previous studies on dispirooxindoles (Ravikumar et al., 2015a,b), we report herein the structural studies of new benzyl and acetyl derivatives, namely 1,1''-dibenzyl-5'-(4-chlorophenyl)-4'-phenyl-4',5'-dihydrodispiro[indoline-3,\ 2'-furan-3',3''-indoline]-2,2''-dione, (I), 1''-acetyl-1-benzyl-5'-(4-chlorophenyl)-4'-phenyl-4',5'-\ dihydrodispiro[indoline-3,2'-furan-3',3''-indoline]-2,2''-dione, (II), 1''-acetyl-1-benzyl-4',5'-diphenyl-4',5'-dihydrodispiro[indoline-3,2'-furan-\ 3',3''-indoline]-2,2''-dione, (III), and 1''-acetyl-1-benzyl-4',5'-diphenyl-4',5'-dihydrodispiro[indoline-3,2'-furan-\ 3',3''-indoline]-2,2''-dione acetonitrile hemisolvate, (IV). The primary goal for the X-ray analyses of the title compounds was to confirm the stereochemistries of the molecules and to obtain detailed information on the structural conformation that may be useful in understanding the chemical reactivity.
The syntheses of compounds (I), (II) and (III) has been described by Reddy et al. (2015). Colourless well-shaped crystals were grown by dissolving 20 mg of (I), (II) and (III) in a methanol–dichloromethane mixture (20 ml, 1:1 v/v), followed by slow evaporation of the solvent mixture under ambient conditions over a period of 3–4 d. Crystals of (IV) were obtained by slow evaporation of a solution of compound (III) in acetonitrile (10 ml).
Crystal data, data collection and structure refinement details are summarized in Table 1. Crystal data, data collection and structure refinement details are summarized in Table 1. All C-bound H atoms of (I), (II), (III) and (IV) were located in difference density maps but were positioned geometrically and included as riding atoms, with C—H = 0.93–0.98 Å and with Uiso(H) values of 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) otherwise. The site-occupancy factors of disordered atoms N3/C40/C41 of the acetonitrile solvent molecule of (IV) refined to 0.654 (19) and 0.346 (19). The C—C and C—N distances of the disordered groups were restrainted to 1.55 (2)and 1.15 (2) Å, respectively. A similarity restraint (the command SIMU within SHELXL2014; Sheldrick, 2015) was applied to N3—C40—C41. Owing to poor quality and diffraction ability of the crystal, the data set of (III) contains a large number of weak high-angle reflections, which accounts for the high K values in the analysis of variance. Hence, the SHEL command was used to cut off the weak high-angle reflections.
The title compounds (I)–(IV) were produced through a three-component coupling reaction between α-diazoamide, aldehyde and 3-arylideneoxindole using a catalytic amount of Rh2(OAc)4 in a one-pot synthesis. The reaction proceeds via an in situ carbonyl ylide formation followed by 1,3-dipolar cycloaddition, creating a central heterocyclic furan ring with the simultaneous formation of four contiguous chiral centres (C7, C9, C10 and C11), of which two (C7 and C11) are spiro all-carbon quaternary centres. The presence of four chiral centres leads to the existence of as many as 16 stereoisomers, of which four pairs are enantiomers (nonsuperimposable mirror-image relationship), whilst the remaining four pairs are diastereomers (nonsuperimposable nonmirror-image relationship). Compounds (I)–(IV) crystallize in centrosymmetric space groups as racemic mixtures (SSSR and RRRS).
As shown in Table 1, compounds (I)–(IV) crystallize in the same triclinic system and the space group P1 with diverse cell dimensions. Compound (IV) is an acetonitrile solvate of (III). Apart from (I), compounds (II)–(IV) crystallize with two molecules in the asymmetric unit (Figs. 1–4). A common numbering system has been used for all the structures. The values of the geometrical parameters when applicable to two molecules in (II)–(IV) are denoted as molecule A/molecule B. The four substituents of the central dihydrofuran ring are arranged in an all-trans configuration, thus avoiding steric hindrance between the aryl groups. The bond lengths (Allen et al., 1987) and angles in all four structures are in agreement with similar structures reported in the literature (Ravikumar et al., 2015b; Girgis et al., 2015). The dihydrofuran ring adopts an envelope conformation, with atom O2 as the flap in (I), (II), (III) (molecule A) and (IV) (molecule B), while it is twisted on the C9—O2 bond in (III) (molecule B) and (IV) (molecule A). The puckering parameter Φ is 357.4 (4) in (I), 358.1 (4)/191.7 (4) in (II), 185.3 (5)/334.1 (4) in (III) and 332.5 (3)/2.1 (3) in (IV). The expected Φ (Cremer & Pople, 1975) is k × 36° for envelope and k × 36 + 18° for a twisted conformation, where k is an integer.
As reported by Reddy et al. (2015), the [3+2] cycloaddition reaction can result in two possible dispirocyclic regioisomers, with spirocentres either at the 1,2-positions (C7 and C11) or at the 1,3-positions (C7 and C10) of the dihydrofuran ring. Title structures (I)–(IV) confirm the exclusive formation of the 1,2-isomer. The two asymmetric H atoms of dihydrofuran (H9 and H10) are in a trans orientation in all four structures [H9—C9—C10—H10 = -152° for (I), 145/-154° for (II), 149/-169° for (III) and 171/-150° for (IV)]. Also, the two oxindole rings at the 1,2-positions are in a trans orientation and facilitate the two carbonyl O atoms to participate in intramolecular C9—H9···O1 and C10—H10···O3 interactions with the trans-related H9 and H10 atoms of the dihydrofuran ring. The t trans orientation also provide C5—H5···O3 and C13—H13···O1 interactions between the oxindole rings. Furthermore, the two oxindole rings show a closer proximity to one another, resulting in possible π–π contacts. The distances between the centroids of the pyrrolone rings (N1/C1/C6/C7/C8 and N2/C11/C12/C17/C18) of oxindole are 3.1720 (11) Å in (I), 3.0261 (15)/3.0424 (15) Å in (II), 3.0444 (18)/3.0861 (19) Å in (III) and 3.0430 (13)/3.0451 (12) Å in (IV). The combination of C—H···O and π–π interactions facilitates the positioning of the oxindole rings in all the four structures, as also seen in previous structures (Ravikumar et al., 2015b).
The C9 and C10 phenyl rings on the dihydrofuran ring are twisted to be nearly orthogonal to each other. The dihedral angles between the planes of the phenyl rings are 69.28 (13)° in (I), 80.52 (14)/80.85 (13)° in (II), 75.41 (17)/84.71 (16)° in (III) and 82.68 (11)/75.98 (12)° in (IV). In (II)–(IV), the planar orientation of the acetyl group of the oxindole is governed by an intramolecular C16—H16···O4 interaction. The benzyl group at atom N1 of the oxindole ring, substituted at C7 of the dihydrofuran ring, plays an interesting role in all the four structures. The benzyl ring is oriented in such a way that it participates in an intramolecular C33—H ···π interaction with the adjacent oxindole phenyl ring (C12–C17), substituted at atom C11 of the dihydrofuran ring. The presence of a benzyl group in (I) instead of the acetyl group in (II)–(IV) forms a C38—H38A···O3 interaction. An overlay of (I)–(IV), superimposing the C atoms of the dihydrofuran ring (Fig. 5), reveals significant dissimilarities in their conformations.
The 1,3-dipolar cycloaddition reaction involves bond formation between 4π electrons 1,3-dipole (carbonyl ylide) and 2π electrons dipolarophile [(E)-arylideneoxindole] systems. Depending on the nature of reactants, the reaction is favored by HOMO–LUMO energy gap (HOMO is the highest occupied molecular orbital and LUMO is the lowest unoccupied molecular orbital) between frontier molecular orbitals (FMO), i.e. HOMO(dipole)–LUMO(dipolarophile) or LUMO(dipole)–HOMO(dipolarophile), or a combination of both. A smaller HOMO–LUMO energy gap normally indicates higher reactivity. Computational calculations were performed for the above said two reactant systems separately, in the absence of the Rh catalyst, using the density functional theory (DFT) methods performed at the B3LYP hybrid exchange correlation functional level (Becke, 1993; Lee et al., 1988) using the 6-31G(d,p) basis set (Bauschlicher & Partridge, 1995) as implemented in GAUSSIAN03 (Frisch et al. , 2004). These calculations are only a rough approximation, suggesting the cycloadduct formation between the HOMO of carbonyl ylide and the LUMO of (E)-arylideneoxindole since the HOMO–LUMO energy gap (ΔE = 2.75 eV) is found to be smaller than that of the LUMO of carbonyl ylide and the HOMO of (E)-arylideneoxindole (ΔE = 3.02 eV).
An attempt has been made to rationalize the diastereoselectivity observed in compounds (I)–(IV). The in-situ-generated carbonyl ylide can exist in an equilibrium between the E and Z forms. The presence of the C9—H9···O1 interaction seen in (I)–(IV) suggests that the [3+2] cycloaddition reaction might have taken place between the E form of the carbonyl ylide and arylideneoxindole. Computational studies also indicated that the E form of the carbonyl ylide is more stable than the Z form by 4.27 kcal mol-1, stabilized by an intramolecular C—H···O interaction. Further, the E form of the carbonyl ylide can add to the arylideneoxindole in two possible ways, either in an exo or an endo fashion, as schematically depicted in Fig. 6. This would lead to an enantiomerically related exo and endo cycloadducts (RRRS and SSSR) as observed in (I)–(IV). The closeness of the oxindole rings could provide secondary stabilizing interactions, e.g. π–π and C—H···O, in both the endo and exo forms. In describing the diastereoselective synthesis of 1,2-diamines, Wang et al. (2003) suggested the importance of intramolecular interactions and the presence of π–π interactions. The present structures show a trans orientation of the oxindole rings and the H atoms of the dihydrofuran ring, facilitating C—H···O and π–π interactions which support the role of weak interactions in promoting both the regio- and diastereoselectivity of dispirooxindoles.
The molecular assembly in (I)–(IV) is governed by the weak interactions (Tables 2–5), as noticed in the prototype oxindole polymorphic systems (Flakus & Hachula, 2011). In (I), two inversion-related dispiroxindole molecules are linked by symmetry-related C31—H31A···O2i (see Table 2 for the symmetry code) interactions between dihydrofuran O and benzyl CH atoms to form a cyclic centrosymmetric dimer characterized by an R22(12) motif (Etter, 1990; Etter et al., 1990; Bernstein et al., 1995). The dimers are interconnected by two independent C3—H3···Cg1ii and C27—H27···Cg2iii interactions (Cg1 is the centroid of the C32–C37 ring and Cg2 is the centroid of the C1–C6 ring) to form a one-dimensional ribbon along the a axis (Fig. 7). The oxindole rings linked by π–π interactions [3.8870 (14)/4.0703 (16) Å for the centroid–centroid distance between the N1/C1/C6/C7/C8 and C1–C6 rings] form centrosymmetric dimers (A···A and B···B) in (II). Adjacent dimers are linked by C15A—H15A···Cg3 interactions involving oxindole and phenyl rings (Cg3 is centroid of the C19B–C24B ring) to form a one-dimensional chain diagonally along the ab plane. Further, a C27B—H27B···O1Ai (see Table 3 for symmetry code) interaction between chlorophenyl and oxindole rings links these chains and extends the molecules into a two-dimensional network (Fig. 8). In (III), the combination of π–π interactions between oxindole rings [3.9256 (19) Å between the centroids of the C12A–C17A and C12B–C117B rings], C31B—H31C···Cg3iv (Cg3 is a centroid of the C25A—C30A ring; see Table 4 for symmetry code) and C24A—H24A···Cg2iii (Cg2 is the centroid of the C32B–C37B ring) interactions between benzyl and phenyl rings, form a cyclic tetramer. A centrosymmetric C27A—H27A···O1Ai interaction between phenyl and oxindole rings interconnect cyclic tetramers extending into a one-dimensional ribbon along the b axis. A C3A—H3A···Cg1ii (Cg1 is the centroid of the C19B–C24B ring) interaction between oxindole and phenyl rings completes a two-dimensional network (Fig. 9).
In (IV), molecules A and B, form independent C—H···O hydrogen-bonded dimers (A···A and B···B) between acetyl and benzyl (C34A—H34A···O4Aii; see Table 5 for the symmetry code), and phenyl and oxindole rings (C27B—H27B···O1Bi). The dimers of molecule A are extended into a one-dimensional ribbon along the a axis by a C39A—H39C···Cg2iv (Cg2 is the centroid of the C32A–C37A ring) interaction between acetyl and benzyl rings. Molecule B acts as bridging linker between two parallel one-dimensioni ribbons of molecule A, through a C3—H3B···Cg1iii (Cg1 is the centroid of the C19A–C24A ring) interaction between oxindole and phenyl rings and a C24B—H24B···.Cg2iv interaction between phenyl and benzyl rings, extending the ribbons into a two-dimensional network (Fig. 10). The acetonitrile solvent molecule appears to play only a space-filling role; it is not involved in any interaction and is instead disordered.
In conclusion, the crystal structures of dispiroxindole derivatives have revealed salient features for understanding the diastereoselectivity of the [3+2] cycloaddition reaction occurring during the synthesis of these compounds. Weak interactions, viz. C—H···O, π–π and C—H···π, play a significant role in structural stability and molecular assembly.
For all compounds, data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for (I), (IV); SHELXS97 (Sheldrick, 2015) for (II), (III). For all compounds, program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg & Putz, 2005) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).
C44H33ClN2O3 | F(000) = 704 |
Mr = 673.17 | Dx = 1.311 Mg m−3 |
Triclinic, P1 | Melting point: 462 K |
a = 10.1099 (10) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.3367 (11) Å | Cell parameters from 6765 reflections |
c = 17.0315 (17) Å | θ = 2.2–28.1° |
α = 74.755 (2)° | µ = 0.16 mm−1 |
β = 78.503 (2)° | T = 294 K |
γ = 65.557 (2)° | Block, colorless |
V = 1705.4 (3) Å3 | 0.15 × 0.08 × 0.06 mm |
Z = 2 |
Bruker SMART APEX CCD area-detector diffractometer | 6578 reflections with I > 2σ(I) |
ω scans | Rint = 0.020 |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | θmax = 28.3°, θmin = 2.0° |
Tmin = 0.92, Tmax = 0.98 | h = −13→13 |
20091 measured reflections | k = −15→14 |
8008 independent reflections | l = −22→22 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.066 | H-atom parameters constrained |
wR(F2) = 0.155 | w = 1/[σ2(Fo2) + (0.0604P)2 + 0.5199P] where P = (Fo2 + 2Fc2)/3 |
S = 1.13 | (Δ/σ)max = 0.001 |
8008 reflections | Δρmax = 0.32 e Å−3 |
451 parameters | Δρmin = −0.17 e Å−3 |
C44H33ClN2O3 | γ = 65.557 (2)° |
Mr = 673.17 | V = 1705.4 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.1099 (10) Å | Mo Kα radiation |
b = 11.3367 (11) Å | µ = 0.16 mm−1 |
c = 17.0315 (17) Å | T = 294 K |
α = 74.755 (2)° | 0.15 × 0.08 × 0.06 mm |
β = 78.503 (2)° |
Bruker SMART APEX CCD area-detector diffractometer | 8008 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 6578 reflections with I > 2σ(I) |
Tmin = 0.92, Tmax = 0.98 | Rint = 0.020 |
20091 measured reflections |
R[F2 > 2σ(F2)] = 0.066 | 0 restraints |
wR(F2) = 0.155 | H-atom parameters constrained |
S = 1.13 | Δρmax = 0.32 e Å−3 |
8008 reflections | Δρmin = −0.17 e Å−3 |
451 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.7853 (2) | 0.98539 (19) | 0.56546 (10) | 0.0424 (4) | |
C2 | 0.7003 (2) | 0.9799 (2) | 0.51362 (12) | 0.0510 (5) | |
H2 | 0.6244 | 1.0552 | 0.4913 | 0.061* | |
C3 | 0.7325 (2) | 0.8577 (2) | 0.49614 (13) | 0.0568 (5) | |
H3 | 0.6768 | 0.8507 | 0.4615 | 0.068* | |
C4 | 0.8448 (2) | 0.7467 (2) | 0.52889 (13) | 0.0571 (5) | |
H4 | 0.8666 | 0.6667 | 0.5143 | 0.069* | |
C5 | 0.9262 (2) | 0.7524 (2) | 0.58334 (12) | 0.0491 (4) | |
H5 | 1.0013 | 0.6768 | 0.6061 | 0.059* | |
C6 | 0.89358 (19) | 0.87246 (19) | 0.60296 (10) | 0.0401 (4) | |
C7 | 0.97125 (18) | 0.91257 (18) | 0.65156 (10) | 0.0390 (4) | |
C8 | 0.9074 (2) | 1.06524 (19) | 0.62420 (10) | 0.0426 (4) | |
C9 | 1.19816 (19) | 0.86550 (19) | 0.68953 (10) | 0.0415 (4) | |
H9 | 1.2004 | 0.9540 | 0.6786 | 0.050* | |
C10 | 1.10768 (19) | 0.84000 (19) | 0.77221 (10) | 0.0419 (4) | |
H10 | 1.1482 | 0.7441 | 0.7925 | 0.050* | |
C11 | 0.95038 (19) | 0.87418 (18) | 0.74903 (10) | 0.0392 (4) | |
C12 | 0.81795 (19) | 0.9682 (2) | 0.79171 (10) | 0.0430 (4) | |
C13 | 0.7773 (2) | 1.0974 (2) | 0.79902 (12) | 0.0534 (5) | |
H13 | 0.8373 | 1.1436 | 0.7743 | 0.064* | |
C14 | 0.6456 (3) | 1.1576 (3) | 0.84378 (13) | 0.0652 (6) | |
H14 | 0.6180 | 1.2446 | 0.8487 | 0.078* | |
C15 | 0.5558 (3) | 1.0909 (3) | 0.88073 (14) | 0.0709 (7) | |
H15 | 0.4678 | 1.1336 | 0.9098 | 0.085* | |
C16 | 0.5944 (2) | 0.9617 (3) | 0.87530 (13) | 0.0646 (6) | |
H16 | 0.5343 | 0.9158 | 0.9006 | 0.077* | |
C17 | 0.7259 (2) | 0.9020 (2) | 0.83089 (11) | 0.0491 (5) | |
C18 | 0.9219 (2) | 0.7450 (2) | 0.77491 (11) | 0.0458 (4) | |
C19 | 1.1263 (2) | 0.9000 (2) | 0.83660 (12) | 0.0525 (5) | |
C20 | 1.1195 (3) | 1.0282 (3) | 0.82109 (16) | 0.0700 (7) | |
H20 | 1.0962 | 1.0831 | 0.7704 | 0.084* | |
C21 | 1.1474 (3) | 1.0756 (4) | 0.8810 (2) | 0.0936 (10) | |
H21 | 1.1422 | 1.1621 | 0.8703 | 0.112* | |
C22 | 1.1825 (3) | 0.9950 (5) | 0.9559 (2) | 0.1032 (12) | |
H22 | 1.2010 | 1.0270 | 0.9958 | 0.124* | |
C23 | 1.1900 (3) | 0.8687 (4) | 0.97173 (18) | 0.1010 (11) | |
H23 | 1.2146 | 0.8142 | 1.0223 | 0.121* | |
C24 | 1.1612 (3) | 0.8206 (3) | 0.91275 (14) | 0.0731 (7) | |
H24 | 1.1653 | 0.7344 | 0.9244 | 0.088* | |
C25 | 1.35044 (19) | 0.76256 (19) | 0.68628 (10) | 0.0415 (4) | |
C26 | 1.4692 (2) | 0.7934 (2) | 0.68647 (12) | 0.0497 (5) | |
H26 | 1.4551 | 0.8799 | 0.6862 | 0.060* | |
C27 | 1.6089 (2) | 0.6964 (2) | 0.68711 (13) | 0.0568 (5) | |
H27 | 1.6886 | 0.7176 | 0.6868 | 0.068* | |
C28 | 1.6286 (2) | 0.5690 (2) | 0.68822 (13) | 0.0555 (5) | |
C29 | 1.5125 (2) | 0.5354 (2) | 0.68768 (13) | 0.0541 (5) | |
H29 | 1.5273 | 0.4486 | 0.6881 | 0.065* | |
C30 | 1.3740 (2) | 0.6329 (2) | 0.68652 (11) | 0.0480 (4) | |
H30 | 1.2950 | 0.6113 | 0.6859 | 0.058* | |
C31 | 0.6959 (2) | 1.2332 (2) | 0.55049 (12) | 0.0511 (5) | |
H31A | 0.7021 | 1.2448 | 0.4916 | 0.061* | |
H31B | 0.7323 | 1.2933 | 0.5618 | 0.061* | |
C32 | 0.5377 (2) | 1.26988 (19) | 0.58486 (11) | 0.0465 (4) | |
C33 | 0.4951 (2) | 1.2084 (2) | 0.66118 (13) | 0.0602 (5) | |
H33 | 0.5644 | 1.1372 | 0.6914 | 0.072* | |
C34 | 0.3508 (3) | 1.2519 (3) | 0.69286 (16) | 0.0778 (7) | |
H34 | 0.3233 | 1.2095 | 0.7442 | 0.093* | |
C35 | 0.2464 (3) | 1.3579 (3) | 0.64899 (19) | 0.0786 (8) | |
H35 | 0.1494 | 1.3884 | 0.6712 | 0.094* | |
C36 | 0.2868 (3) | 1.4174 (2) | 0.57281 (17) | 0.0676 (6) | |
H36 | 0.2169 | 1.4881 | 0.5427 | 0.081* | |
C37 | 0.4307 (2) | 1.3732 (2) | 0.54047 (14) | 0.0556 (5) | |
H37 | 0.4567 | 1.4132 | 0.4880 | 0.067* | |
C38 | 0.7306 (3) | 0.6702 (3) | 0.86056 (14) | 0.0673 (6) | |
H38A | 0.7872 | 0.5907 | 0.8388 | 0.081* | |
H38B | 0.6307 | 0.7005 | 0.8484 | 0.081* | |
C39 | 0.7333 (3) | 0.6362 (2) | 0.95236 (13) | 0.0590 (5) | |
C40 | 0.8370 (3) | 0.6445 (3) | 0.98913 (15) | 0.0720 (7) | |
H40 | 0.9066 | 0.6755 | 0.9574 | 0.086* | |
C41 | 0.8387 (4) | 0.6067 (3) | 1.07362 (17) | 0.0852 (8) | |
H41 | 0.9094 | 0.6126 | 1.0982 | 0.102* | |
C42 | 0.7373 (4) | 0.5613 (3) | 1.12024 (17) | 0.0889 (10) | |
H42 | 0.7387 | 0.5361 | 1.1767 | 0.107* | |
C43 | 0.6335 (4) | 0.5524 (3) | 1.08463 (18) | 0.0904 (9) | |
H43 | 0.5649 | 0.5204 | 1.1168 | 0.108* | |
C44 | 0.6299 (3) | 0.5909 (3) | 1.00097 (16) | 0.0764 (7) | |
H44 | 0.5575 | 0.5863 | 0.9771 | 0.092* | |
Cl1 | 1.80351 (7) | 0.44690 (8) | 0.68860 (6) | 0.0992 (3) | |
N1 | 0.78866 (17) | 1.09873 (15) | 0.58347 (9) | 0.0450 (4) | |
N2 | 0.78804 (19) | 0.77128 (18) | 0.81948 (10) | 0.0524 (4) | |
O1 | 0.95298 (16) | 1.14096 (14) | 0.63705 (9) | 0.0537 (3) | |
O2 | 1.12322 (13) | 0.85615 (13) | 0.62992 (7) | 0.0430 (3) | |
O3 | 1.00378 (17) | 0.63808 (15) | 0.76013 (9) | 0.0584 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0431 (9) | 0.0532 (11) | 0.0321 (8) | −0.0220 (8) | 0.0014 (7) | −0.0086 (7) |
C2 | 0.0475 (11) | 0.0659 (13) | 0.0399 (10) | −0.0233 (10) | −0.0097 (8) | −0.0047 (9) |
C3 | 0.0597 (13) | 0.0791 (15) | 0.0455 (11) | −0.0356 (12) | −0.0110 (9) | −0.0159 (10) |
C4 | 0.0656 (13) | 0.0653 (13) | 0.0531 (12) | −0.0312 (11) | −0.0058 (10) | −0.0225 (10) |
C5 | 0.0475 (10) | 0.0555 (12) | 0.0463 (10) | −0.0198 (9) | −0.0034 (8) | −0.0143 (9) |
C6 | 0.0394 (9) | 0.0535 (11) | 0.0304 (8) | −0.0219 (8) | 0.0007 (7) | −0.0100 (7) |
C7 | 0.0372 (9) | 0.0512 (10) | 0.0302 (8) | −0.0193 (8) | 0.0006 (7) | −0.0100 (7) |
C8 | 0.0445 (10) | 0.0544 (11) | 0.0316 (8) | −0.0235 (9) | 0.0041 (7) | −0.0113 (8) |
C9 | 0.0406 (9) | 0.0542 (11) | 0.0356 (9) | −0.0230 (8) | −0.0011 (7) | −0.0127 (8) |
C10 | 0.0386 (9) | 0.0553 (11) | 0.0334 (9) | −0.0192 (8) | −0.0014 (7) | −0.0113 (8) |
C11 | 0.0396 (9) | 0.0515 (10) | 0.0298 (8) | −0.0206 (8) | −0.0019 (7) | −0.0093 (7) |
C12 | 0.0392 (9) | 0.0591 (11) | 0.0302 (8) | −0.0179 (8) | −0.0026 (7) | −0.0102 (8) |
C13 | 0.0554 (12) | 0.0621 (13) | 0.0422 (10) | −0.0187 (10) | −0.0042 (9) | −0.0167 (9) |
C14 | 0.0631 (14) | 0.0719 (15) | 0.0475 (12) | −0.0067 (12) | −0.0049 (10) | −0.0232 (11) |
C15 | 0.0472 (12) | 0.0950 (19) | 0.0461 (12) | −0.0049 (12) | 0.0036 (10) | −0.0179 (12) |
C16 | 0.0446 (11) | 0.0945 (19) | 0.0443 (11) | −0.0250 (12) | 0.0038 (9) | −0.0063 (11) |
C17 | 0.0432 (10) | 0.0686 (13) | 0.0337 (9) | −0.0227 (9) | −0.0026 (7) | −0.0064 (8) |
C18 | 0.0510 (11) | 0.0589 (12) | 0.0325 (9) | −0.0272 (10) | −0.0057 (8) | −0.0061 (8) |
C19 | 0.0407 (10) | 0.0829 (15) | 0.0418 (10) | −0.0255 (10) | 0.0005 (8) | −0.0258 (10) |
C20 | 0.0709 (15) | 0.0964 (19) | 0.0645 (14) | −0.0460 (14) | 0.0071 (12) | −0.0390 (13) |
C21 | 0.0862 (19) | 0.138 (3) | 0.097 (2) | −0.066 (2) | 0.0178 (17) | −0.072 (2) |
C22 | 0.083 (2) | 0.180 (4) | 0.079 (2) | −0.054 (2) | 0.0011 (16) | −0.080 (2) |
C23 | 0.088 (2) | 0.162 (3) | 0.0582 (16) | −0.033 (2) | −0.0182 (14) | −0.0454 (19) |
C24 | 0.0630 (14) | 0.109 (2) | 0.0450 (12) | −0.0238 (14) | −0.0088 (10) | −0.0243 (12) |
C25 | 0.0406 (9) | 0.0590 (11) | 0.0296 (8) | −0.0237 (8) | 0.0004 (7) | −0.0122 (7) |
C26 | 0.0470 (10) | 0.0613 (12) | 0.0488 (11) | −0.0274 (9) | −0.0021 (8) | −0.0148 (9) |
C27 | 0.0428 (11) | 0.0782 (15) | 0.0552 (12) | −0.0288 (10) | −0.0054 (9) | −0.0131 (11) |
C28 | 0.0417 (10) | 0.0682 (14) | 0.0483 (11) | −0.0127 (10) | −0.0042 (8) | −0.0122 (10) |
C29 | 0.0579 (12) | 0.0554 (12) | 0.0494 (11) | −0.0204 (10) | −0.0024 (9) | −0.0157 (9) |
C30 | 0.0465 (10) | 0.0619 (12) | 0.0435 (10) | −0.0275 (9) | −0.0026 (8) | −0.0139 (9) |
C31 | 0.0573 (12) | 0.0505 (11) | 0.0402 (10) | −0.0195 (9) | −0.0038 (9) | −0.0030 (8) |
C32 | 0.0537 (11) | 0.0479 (11) | 0.0418 (10) | −0.0190 (9) | −0.0085 (8) | −0.0138 (8) |
C33 | 0.0550 (12) | 0.0776 (15) | 0.0439 (11) | −0.0228 (11) | −0.0067 (9) | −0.0086 (10) |
C34 | 0.0627 (15) | 0.113 (2) | 0.0576 (14) | −0.0375 (15) | 0.0054 (12) | −0.0198 (14) |
C35 | 0.0482 (13) | 0.098 (2) | 0.095 (2) | −0.0211 (13) | −0.0013 (13) | −0.0426 (17) |
C36 | 0.0591 (14) | 0.0591 (14) | 0.0866 (18) | −0.0118 (11) | −0.0220 (13) | −0.0248 (13) |
C37 | 0.0667 (14) | 0.0487 (11) | 0.0566 (12) | −0.0219 (10) | −0.0162 (10) | −0.0122 (9) |
C38 | 0.0784 (16) | 0.0913 (18) | 0.0509 (12) | −0.0587 (14) | −0.0035 (11) | −0.0036 (11) |
C39 | 0.0668 (14) | 0.0601 (13) | 0.0486 (11) | −0.0296 (11) | 0.0022 (10) | −0.0057 (10) |
C40 | 0.0768 (16) | 0.0834 (17) | 0.0564 (14) | −0.0349 (14) | −0.0057 (12) | −0.0085 (12) |
C41 | 0.103 (2) | 0.0760 (18) | 0.0642 (16) | −0.0161 (16) | −0.0228 (16) | −0.0136 (13) |
C42 | 0.126 (3) | 0.0601 (16) | 0.0488 (14) | −0.0142 (16) | 0.0049 (16) | −0.0046 (12) |
C43 | 0.111 (2) | 0.0765 (18) | 0.0643 (17) | −0.0380 (18) | 0.0261 (17) | −0.0052 (14) |
C44 | 0.0867 (18) | 0.0753 (16) | 0.0647 (15) | −0.0430 (15) | 0.0129 (13) | −0.0054 (12) |
Cl1 | 0.0510 (4) | 0.0867 (5) | 0.1342 (7) | −0.0032 (3) | −0.0095 (4) | −0.0188 (5) |
N1 | 0.0481 (9) | 0.0479 (9) | 0.0379 (8) | −0.0186 (7) | −0.0049 (7) | −0.0059 (7) |
N2 | 0.0540 (10) | 0.0692 (11) | 0.0401 (8) | −0.0357 (9) | 0.0009 (7) | −0.0049 (8) |
O1 | 0.0594 (8) | 0.0579 (8) | 0.0537 (8) | −0.0321 (7) | −0.0016 (6) | −0.0141 (6) |
O2 | 0.0372 (6) | 0.0621 (8) | 0.0319 (6) | −0.0206 (6) | 0.0001 (5) | −0.0134 (5) |
O3 | 0.0706 (10) | 0.0536 (9) | 0.0530 (8) | −0.0264 (8) | −0.0027 (7) | −0.0124 (7) |
C1—C2 | 1.377 (3) | C22—H22 | 0.9300 |
C1—C6 | 1.391 (3) | C23—C24 | 1.388 (4) |
C1—N1 | 1.412 (2) | C23—H23 | 0.9300 |
C2—C3 | 1.386 (3) | C24—H24 | 0.9300 |
C2—H2 | 0.9300 | C25—C26 | 1.383 (3) |
C3—C4 | 1.373 (3) | C25—C30 | 1.388 (3) |
C3—H3 | 0.9300 | C26—C27 | 1.386 (3) |
C4—C5 | 1.386 (3) | C26—H26 | 0.9300 |
C4—H4 | 0.9300 | C27—C28 | 1.369 (3) |
C5—C6 | 1.377 (3) | C27—H27 | 0.9300 |
C5—H5 | 0.9300 | C28—C29 | 1.378 (3) |
C6—C7 | 1.504 (2) | C28—Cl1 | 1.737 (2) |
C7—O2 | 1.411 (2) | C29—C30 | 1.379 (3) |
C7—C8 | 1.549 (3) | C29—H29 | 0.9300 |
C7—C11 | 1.596 (2) | C30—H30 | 0.9300 |
C8—O1 | 1.210 (2) | C31—N1 | 1.447 (2) |
C8—N1 | 1.372 (2) | C31—C32 | 1.509 (3) |
C9—O2 | 1.430 (2) | C31—H31A | 0.9700 |
C9—C25 | 1.499 (3) | C31—H31B | 0.9700 |
C9—C10 | 1.547 (2) | C32—C33 | 1.382 (3) |
C9—H9 | 0.9800 | C32—C37 | 1.388 (3) |
C10—C19 | 1.511 (3) | C33—C34 | 1.376 (3) |
C10—C11 | 1.580 (2) | C33—H33 | 0.9300 |
C10—H10 | 0.9800 | C34—C35 | 1.382 (4) |
C11—C12 | 1.515 (2) | C34—H34 | 0.9300 |
C11—C18 | 1.543 (3) | C35—C36 | 1.365 (4) |
C12—C13 | 1.380 (3) | C35—H35 | 0.9300 |
C12—C17 | 1.394 (3) | C36—C37 | 1.376 (3) |
C13—C14 | 1.392 (3) | C36—H36 | 0.9300 |
C13—H13 | 0.9300 | C37—H37 | 0.9300 |
C14—C15 | 1.371 (4) | C38—N2 | 1.451 (3) |
C14—H14 | 0.9300 | C38—C39 | 1.512 (3) |
C15—C16 | 1.375 (4) | C38—H38A | 0.9700 |
C15—H15 | 0.9300 | C38—H38B | 0.9700 |
C16—C17 | 1.386 (3) | C39—C40 | 1.369 (3) |
C16—H16 | 0.9300 | C39—C44 | 1.385 (3) |
C17—N2 | 1.401 (3) | C40—C41 | 1.391 (4) |
C18—O3 | 1.211 (2) | C40—H40 | 0.9300 |
C18—N2 | 1.368 (2) | C41—C42 | 1.359 (5) |
C19—C20 | 1.382 (3) | C41—H41 | 0.9300 |
C19—C24 | 1.387 (3) | C42—C43 | 1.360 (5) |
C20—C21 | 1.392 (3) | C42—H42 | 0.9300 |
C20—H20 | 0.9300 | C43—C44 | 1.379 (4) |
C21—C22 | 1.374 (5) | C43—H43 | 0.9300 |
C21—H21 | 0.9300 | C44—H44 | 0.9300 |
C22—C23 | 1.358 (5) | ||
C2—C1—C6 | 121.94 (18) | C22—C23—H23 | 119.8 |
C2—C1—N1 | 128.07 (18) | C24—C23—H23 | 119.8 |
C6—C1—N1 | 109.76 (15) | C19—C24—C23 | 120.6 (3) |
C1—C2—C3 | 117.25 (19) | C19—C24—H24 | 119.7 |
C1—C2—H2 | 121.4 | C23—C24—H24 | 119.7 |
C3—C2—H2 | 121.4 | C26—C25—C30 | 118.76 (18) |
C4—C3—C2 | 121.36 (18) | C26—C25—C9 | 120.89 (17) |
C4—C3—H3 | 119.3 | C30—C25—C9 | 120.29 (16) |
C2—C3—H3 | 119.3 | C25—C26—C27 | 120.5 (2) |
C3—C4—C5 | 120.9 (2) | C25—C26—H26 | 119.7 |
C3—C4—H4 | 119.6 | C27—C26—H26 | 119.7 |
C5—C4—H4 | 119.6 | C28—C27—C26 | 119.40 (19) |
C6—C5—C4 | 118.54 (19) | C28—C27—H27 | 120.3 |
C6—C5—H5 | 120.7 | C26—C27—H27 | 120.3 |
C4—C5—H5 | 120.7 | C27—C28—C29 | 121.41 (19) |
C5—C6—C1 | 119.81 (17) | C27—C28—Cl1 | 119.69 (17) |
C5—C6—C7 | 130.70 (17) | C29—C28—Cl1 | 118.89 (18) |
C1—C6—C7 | 108.81 (16) | C28—C29—C30 | 118.7 (2) |
O2—C7—C6 | 109.39 (13) | C28—C29—H29 | 120.7 |
O2—C7—C8 | 112.61 (14) | C30—C29—H29 | 120.7 |
C6—C7—C8 | 101.82 (14) | C29—C30—C25 | 121.21 (18) |
O2—C7—C11 | 105.24 (13) | C29—C30—H30 | 119.4 |
C6—C7—C11 | 118.86 (14) | C25—C30—H30 | 119.4 |
C8—C7—C11 | 109.14 (13) | N1—C31—C32 | 113.69 (16) |
O1—C8—N1 | 126.35 (19) | N1—C31—H31A | 108.8 |
O1—C8—C7 | 126.35 (17) | C32—C31—H31A | 108.8 |
N1—C8—C7 | 107.30 (15) | N1—C31—H31B | 108.8 |
O2—C9—C25 | 108.44 (14) | C32—C31—H31B | 108.8 |
O2—C9—C10 | 104.79 (13) | H31A—C31—H31B | 107.7 |
C25—C9—C10 | 112.21 (15) | C33—C32—C37 | 118.2 (2) |
O2—C9—H9 | 110.4 | C33—C32—C31 | 122.41 (18) |
C25—C9—H9 | 110.4 | C37—C32—C31 | 119.34 (18) |
C10—C9—H9 | 110.4 | C34—C33—C32 | 120.5 (2) |
C19—C10—C9 | 113.09 (15) | C34—C33—H33 | 119.7 |
C19—C10—C11 | 120.40 (15) | C32—C33—H33 | 119.7 |
C9—C10—C11 | 104.92 (13) | C33—C34—C35 | 120.5 (2) |
C19—C10—H10 | 105.8 | C33—C34—H34 | 119.7 |
C9—C10—H10 | 105.8 | C35—C34—H34 | 119.7 |
C11—C10—H10 | 105.8 | C36—C35—C34 | 119.5 (2) |
C12—C11—C18 | 102.01 (14) | C36—C35—H35 | 120.3 |
C12—C11—C10 | 119.47 (14) | C34—C35—H35 | 120.3 |
C18—C11—C10 | 107.05 (15) | C35—C36—C37 | 120.2 (2) |
C12—C11—C7 | 116.58 (14) | C35—C36—H36 | 119.9 |
C18—C11—C7 | 109.11 (13) | C37—C36—H36 | 119.9 |
C10—C11—C7 | 102.16 (13) | C36—C37—C32 | 121.1 (2) |
C13—C12—C17 | 118.41 (18) | C36—C37—H37 | 119.5 |
C13—C12—C11 | 133.17 (17) | C32—C37—H37 | 119.5 |
C17—C12—C11 | 108.41 (17) | N2—C38—C39 | 113.68 (19) |
C12—C13—C14 | 119.2 (2) | N2—C38—H38A | 108.8 |
C12—C13—H13 | 120.4 | C39—C38—H38A | 108.8 |
C14—C13—H13 | 120.4 | N2—C38—H38B | 108.8 |
C15—C14—C13 | 121.3 (2) | C39—C38—H38B | 108.8 |
C15—C14—H14 | 119.4 | H38A—C38—H38B | 107.7 |
C13—C14—H14 | 119.4 | C40—C39—C44 | 118.7 (2) |
C14—C15—C16 | 120.7 (2) | C40—C39—C38 | 122.4 (2) |
C14—C15—H15 | 119.6 | C44—C39—C38 | 118.8 (2) |
C16—C15—H15 | 119.6 | C39—C40—C41 | 120.4 (3) |
C15—C16—C17 | 117.8 (2) | C39—C40—H40 | 119.8 |
C15—C16—H16 | 121.1 | C41—C40—H40 | 119.8 |
C17—C16—H16 | 121.1 | C42—C41—C40 | 120.1 (3) |
C16—C17—C12 | 122.6 (2) | C42—C41—H41 | 120.0 |
C16—C17—N2 | 127.3 (2) | C40—C41—H41 | 120.0 |
C12—C17—N2 | 110.12 (17) | C41—C42—C43 | 120.3 (3) |
O3—C18—N2 | 125.42 (19) | C41—C42—H42 | 119.9 |
O3—C18—C11 | 126.54 (17) | C43—C42—H42 | 119.9 |
N2—C18—C11 | 108.02 (17) | C42—C43—C44 | 120.1 (3) |
C20—C19—C24 | 118.5 (2) | C42—C43—H43 | 119.9 |
C20—C19—C10 | 122.68 (19) | C44—C43—H43 | 119.9 |
C24—C19—C10 | 118.6 (2) | C43—C44—C39 | 120.4 (3) |
C19—C20—C21 | 120.3 (3) | C43—C44—H44 | 119.8 |
C19—C20—H20 | 119.9 | C39—C44—H44 | 119.8 |
C21—C20—H20 | 119.9 | C8—N1—C1 | 110.56 (16) |
C22—C21—C20 | 120.2 (3) | C8—N1—C31 | 124.31 (17) |
C22—C21—H21 | 119.9 | C1—N1—C31 | 124.22 (16) |
C20—C21—H21 | 119.9 | C18—N2—C17 | 111.27 (16) |
C23—C22—C21 | 120.0 (3) | C18—N2—C38 | 123.5 (2) |
C23—C22—H22 | 120.0 | C17—N2—C38 | 124.50 (18) |
C21—C22—H22 | 120.0 | C7—O2—C9 | 109.18 (12) |
C22—C23—C24 | 120.3 (3) | ||
C6—C1—C2—C3 | −3.7 (3) | C11—C10—C19—C24 | 105.9 (2) |
N1—C1—C2—C3 | 170.20 (18) | C24—C19—C20—C21 | 0.0 (3) |
C1—C2—C3—C4 | −0.3 (3) | C10—C19—C20—C21 | −175.6 (2) |
C2—C3—C4—C5 | 2.6 (3) | C19—C20—C21—C22 | 0.3 (4) |
C3—C4—C5—C6 | −1.0 (3) | C20—C21—C22—C23 | 0.0 (5) |
C4—C5—C6—C1 | −2.8 (3) | C21—C22—C23—C24 | −0.6 (5) |
C4—C5—C6—C7 | −172.29 (18) | C20—C19—C24—C23 | −0.6 (4) |
C2—C1—C6—C5 | 5.4 (3) | C10—C19—C24—C23 | 175.2 (2) |
N1—C1—C6—C5 | −169.57 (16) | C22—C23—C24—C19 | 0.9 (4) |
C2—C1—C6—C7 | 176.93 (16) | O2—C9—C25—C26 | 134.44 (17) |
N1—C1—C6—C7 | 2.00 (19) | C10—C9—C25—C26 | −110.30 (19) |
C5—C6—C7—O2 | 42.1 (2) | O2—C9—C25—C30 | −48.3 (2) |
C1—C6—C7—O2 | −128.21 (15) | C10—C9—C25—C30 | 67.0 (2) |
C5—C6—C7—C8 | 161.46 (18) | C30—C25—C26—C27 | −0.2 (3) |
C1—C6—C7—C8 | −8.87 (17) | C9—C25—C26—C27 | 177.13 (17) |
C5—C6—C7—C11 | −78.7 (2) | C25—C26—C27—C28 | −0.5 (3) |
C1—C6—C7—C11 | 110.99 (17) | C26—C27—C28—C29 | 0.8 (3) |
O2—C7—C8—O1 | −50.7 (2) | C26—C27—C28—Cl1 | 179.73 (16) |
C6—C7—C8—O1 | −167.75 (17) | C27—C28—C29—C30 | −0.4 (3) |
C11—C7—C8—O1 | 65.8 (2) | Cl1—C28—C29—C30 | −179.34 (16) |
O2—C7—C8—N1 | 129.95 (15) | C28—C29—C30—C25 | −0.3 (3) |
C6—C7—C8—N1 | 12.92 (17) | C26—C25—C30—C29 | 0.6 (3) |
C11—C7—C8—N1 | −113.57 (15) | C9—C25—C30—C29 | −176.74 (17) |
O2—C9—C10—C19 | −155.55 (16) | N1—C31—C32—C33 | 25.9 (3) |
C25—C9—C10—C19 | 87.0 (2) | N1—C31—C32—C37 | −157.26 (17) |
O2—C9—C10—C11 | −22.48 (18) | C37—C32—C33—C34 | −2.0 (3) |
C25—C9—C10—C11 | −139.94 (15) | C31—C32—C33—C34 | 174.9 (2) |
C19—C10—C11—C12 | 0.2 (3) | C32—C33—C34—C35 | −0.2 (4) |
C9—C10—C11—C12 | −128.60 (17) | C33—C34—C35—C36 | 1.7 (4) |
C19—C10—C11—C18 | −114.82 (19) | C34—C35—C36—C37 | −0.8 (4) |
C9—C10—C11—C18 | 116.35 (15) | C35—C36—C37—C32 | −1.4 (3) |
C19—C10—C11—C7 | 130.58 (17) | C33—C32—C37—C36 | 2.8 (3) |
C9—C10—C11—C7 | 1.75 (18) | C31—C32—C37—C36 | −174.13 (19) |
O2—C7—C11—C12 | 151.95 (15) | N2—C38—C39—C40 | −30.5 (4) |
C6—C7—C11—C12 | −85.2 (2) | N2—C38—C39—C44 | 151.6 (2) |
C8—C7—C11—C12 | 30.9 (2) | C44—C39—C40—C41 | 0.6 (4) |
O2—C7—C11—C18 | −93.24 (16) | C38—C39—C40—C41 | −177.3 (2) |
C6—C7—C11—C18 | 29.6 (2) | C39—C40—C41—C42 | 0.0 (4) |
C8—C7—C11—C18 | 145.68 (15) | C40—C41—C42—C43 | 0.0 (4) |
O2—C7—C11—C10 | 19.84 (17) | C41—C42—C43—C44 | −0.6 (5) |
C6—C7—C11—C10 | 142.73 (16) | C42—C43—C44—C39 | 1.3 (4) |
C8—C7—C11—C10 | −101.24 (16) | C40—C39—C44—C43 | −1.3 (4) |
C18—C11—C12—C13 | 175.4 (2) | C38—C39—C44—C43 | 176.7 (3) |
C10—C11—C12—C13 | 57.8 (3) | O1—C8—N1—C1 | 168.04 (17) |
C7—C11—C12—C13 | −65.8 (3) | C7—C8—N1—C1 | −12.62 (18) |
C18—C11—C12—C17 | −3.32 (18) | O1—C8—N1—C31 | −1.4 (3) |
C10—C11—C12—C17 | −120.99 (17) | C7—C8—N1—C31 | 177.92 (15) |
C7—C11—C12—C17 | 115.41 (17) | C2—C1—N1—C8 | −167.52 (18) |
C17—C12—C13—C14 | −1.1 (3) | C6—C1—N1—C8 | 7.0 (2) |
C11—C12—C13—C14 | −179.73 (19) | C2—C1—N1—C31 | 1.9 (3) |
C12—C13—C14—C15 | 0.1 (3) | C6—C1—N1—C31 | 176.48 (16) |
C13—C14—C15—C16 | 0.7 (4) | C32—C31—N1—C8 | −121.08 (19) |
C14—C15—C16—C17 | −0.5 (3) | C32—C31—N1—C1 | 70.9 (2) |
C15—C16—C17—C12 | −0.5 (3) | O3—C18—N2—C17 | 175.25 (18) |
C15—C16—C17—N2 | 178.0 (2) | C11—C18—N2—C17 | −3.4 (2) |
C13—C12—C17—C16 | 1.3 (3) | O3—C18—N2—C38 | 4.7 (3) |
C11—C12—C17—C16 | −179.71 (17) | C11—C18—N2—C38 | −173.96 (17) |
C13—C12—C17—N2 | −177.45 (16) | C16—C17—N2—C18 | −177.42 (19) |
C11—C12—C17—N2 | 1.5 (2) | C12—C17—N2—C18 | 1.3 (2) |
C12—C11—C18—O3 | −174.62 (18) | C16—C17—N2—C38 | −7.0 (3) |
C10—C11—C18—O3 | −48.4 (2) | C12—C17—N2—C38 | 171.68 (18) |
C7—C11—C18—O3 | 61.5 (2) | C39—C38—N2—C18 | 105.6 (2) |
C12—C11—C18—N2 | 4.06 (18) | C39—C38—N2—C17 | −63.7 (3) |
C10—C11—C18—N2 | 130.31 (15) | C6—C7—O2—C9 | −165.41 (14) |
C7—C11—C18—N2 | −119.85 (16) | C8—C7—O2—C9 | 82.15 (16) |
C9—C10—C19—C20 | 46.6 (3) | C11—C7—O2—C9 | −36.64 (17) |
C11—C10—C19—C20 | −78.5 (2) | C25—C9—O2—C7 | 157.84 (14) |
C9—C10—C19—C24 | −129.0 (2) | C10—C9—O2—C7 | 37.83 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O3 | 0.93 | 2.55 | 3.067 (2) | 116 |
C9—H9···O1 | 0.98 | 2.60 | 3.115 (2) | 113 |
C10—H10···O3 | 0.98 | 2.45 | 2.951 (2) | 111 |
C13—H13···O1 | 0.93 | 2.40 | 3.011 (3) | 123 |
C31—H31B···O1 | 0.97 | 2.53 | 2.914 (3) | 104 |
C38—H38A···O3 | 0.97 | 2.51 | 2.881 (3) | 103 |
C31—H31A···O2i | 0.97 | 2.61 | 3.417 (2) | 141 |
C3—H3···Cg1(C32–C37)ii | 0.93 | 2.90 | 3.734 (2) | 149 |
C27—H27···Cg2(C1–C6)iii | 0.93 | 2.91 | 3.537 (2) | 126 |
C33—H33···Cg3(C12–C17) | 0.93 | 2.90 | 3.560 (2) | 147 |
Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x+1, −y+2, −z+1; (iii) x+1, y, z. |
C39H29ClN2O4 | F(000) = 1304 |
Mr = 625.09 | Dx = 1.335 Mg m−3 |
Triclinic, P1 | Melting point: 430 K |
a = 11.9830 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.9260 (6) Å | Cell parameters from 6374 reflections |
c = 21.5664 (10) Å | θ = 2.2–21.4° |
α = 76.330 (1)° | µ = 0.17 mm−1 |
β = 76.522 (1)° | T = 294 K |
γ = 77.553 (1)° | Block, colorless |
V = 3110.6 (2) Å3 | 0.13 × 0.11 × 0.06 mm |
Z = 4 |
Bruker SMART APEX CCD area-detector diffractometer | 8962 reflections with I > 2σ(I) |
ω scans | Rint = 0.034 |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | θmax = 28.3°, θmin = 1.7° |
Tmin = 0.94, Tmax = 0.97 | h = −15→16 |
36879 measured reflections | k = −17→16 |
14644 independent reflections | l = −28→28 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.068 | H-atom parameters constrained |
wR(F2) = 0.160 | w = 1/[σ2(Fo2) + (0.0634P)2 + 0.627P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
14644 reflections | Δρmax = 0.27 e Å−3 |
831 parameters | Δρmin = −0.19 e Å−3 |
C39H29ClN2O4 | γ = 77.553 (1)° |
Mr = 625.09 | V = 3110.6 (2) Å3 |
Triclinic, P1 | Z = 4 |
a = 11.9830 (5) Å | Mo Kα radiation |
b = 12.9260 (6) Å | µ = 0.17 mm−1 |
c = 21.5664 (10) Å | T = 294 K |
α = 76.330 (1)° | 0.13 × 0.11 × 0.06 mm |
β = 76.522 (1)° |
Bruker SMART APEX CCD area-detector diffractometer | 14644 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 8962 reflections with I > 2σ(I) |
Tmin = 0.94, Tmax = 0.97 | Rint = 0.034 |
36879 measured reflections |
R[F2 > 2σ(F2)] = 0.068 | 0 restraints |
wR(F2) = 0.160 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.27 e Å−3 |
14644 reflections | Δρmin = −0.19 e Å−3 |
831 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
C1A | 0.8810 (2) | 0.62529 (18) | 0.51557 (11) | 0.0474 (5) | |
C2A | 0.8838 (2) | 0.6694 (2) | 0.45087 (12) | 0.0608 (7) | |
H2A | 0.8303 | 0.6587 | 0.4289 | 0.073* | |
C3A | 0.9694 (3) | 0.7303 (2) | 0.41976 (14) | 0.0707 (8) | |
H3A | 0.9727 | 0.7624 | 0.3761 | 0.085* | |
C4A | 1.0502 (2) | 0.7448 (2) | 0.45157 (14) | 0.0657 (7) | |
H4A | 1.1092 | 0.7834 | 0.4289 | 0.079* | |
C5A | 1.0441 (2) | 0.70198 (18) | 0.51732 (13) | 0.0542 (6) | |
H5A | 1.0977 | 0.7127 | 0.5392 | 0.065* | |
C6A | 0.95706 (18) | 0.64318 (17) | 0.54974 (11) | 0.0448 (5) | |
C7A | 0.93126 (18) | 0.58280 (17) | 0.61892 (11) | 0.0420 (5) | |
C8A | 0.84016 (18) | 0.51592 (17) | 0.61534 (11) | 0.0437 (5) | |
C9A | 1.01708 (19) | 0.48447 (18) | 0.70616 (11) | 0.0472 (6) | |
H9A | 0.9809 | 0.4195 | 0.7201 | 0.057* | |
C10A | 0.93328 (18) | 0.57950 (17) | 0.73395 (11) | 0.0450 (5) | |
H10A | 0.9832 | 0.6219 | 0.7439 | 0.054* | |
C11A | 0.88082 (18) | 0.65210 (16) | 0.67438 (10) | 0.0409 (5) | |
C12A | 0.75275 (18) | 0.69908 (18) | 0.67860 (11) | 0.0442 (5) | |
C13A | 0.65389 (19) | 0.6531 (2) | 0.70518 (11) | 0.0529 (6) | |
H13A | 0.6597 | 0.5806 | 0.7254 | 0.063* | |
C14A | 0.5460 (2) | 0.7169 (2) | 0.70113 (13) | 0.0618 (7) | |
H14A | 0.4788 | 0.6874 | 0.7198 | 0.074* | |
C15A | 0.5371 (2) | 0.8228 (3) | 0.66991 (14) | 0.0679 (8) | |
H15A | 0.4637 | 0.8637 | 0.6675 | 0.081* | |
C16A | 0.6343 (2) | 0.8705 (2) | 0.64199 (14) | 0.0638 (7) | |
H16A | 0.6278 | 0.9423 | 0.6204 | 0.077* | |
C17A | 0.7415 (2) | 0.80706 (19) | 0.64754 (11) | 0.0488 (6) | |
C18A | 0.9361 (2) | 0.75484 (17) | 0.65129 (11) | 0.0450 (5) | |
C19A | 0.85210 (19) | 0.5456 (2) | 0.79726 (12) | 0.0515 (6) | |
C20A | 0.7863 (2) | 0.4650 (2) | 0.80723 (13) | 0.0664 (7) | |
H20A | 0.7904 | 0.4299 | 0.7735 | 0.080* | |
C21A | 0.7146 (3) | 0.4360 (3) | 0.86644 (16) | 0.0829 (10) | |
H21A | 0.6701 | 0.3826 | 0.8722 | 0.099* | |
C22A | 0.7090 (3) | 0.4862 (3) | 0.91689 (16) | 0.0930 (11) | |
H22A | 0.6608 | 0.4666 | 0.9568 | 0.112* | |
C23A | 0.7740 (3) | 0.5648 (3) | 0.90844 (16) | 0.0874 (10) | |
H23A | 0.7708 | 0.5984 | 0.9426 | 0.105* | |
C24A | 0.8449 (2) | 0.5945 (2) | 0.84884 (13) | 0.0660 (7) | |
H24A | 0.8886 | 0.6485 | 0.8434 | 0.079* | |
C25A | 1.13691 (19) | 0.45898 (18) | 0.72273 (11) | 0.0484 (6) | |
C26A | 1.1771 (2) | 0.36208 (19) | 0.75998 (12) | 0.0556 (6) | |
H26A | 1.1286 | 0.3107 | 0.7766 | 0.067* | |
C27A | 1.2882 (2) | 0.3395 (2) | 0.77329 (13) | 0.0636 (7) | |
H27A | 1.3139 | 0.2739 | 0.7989 | 0.076* | |
C28A | 1.3596 (2) | 0.4148 (2) | 0.74830 (13) | 0.0589 (7) | |
C29A | 1.3224 (2) | 0.5117 (2) | 0.71085 (14) | 0.0680 (7) | |
H29A | 1.3717 | 0.5624 | 0.6940 | 0.082* | |
C30A | 1.2114 (2) | 0.5337 (2) | 0.69832 (14) | 0.0650 (7) | |
H30A | 1.1859 | 0.5998 | 0.6731 | 0.078* | |
C31A | 0.7317 (2) | 0.5043 (2) | 0.53220 (14) | 0.0600 (7) | |
H31A | 0.7047 | 0.4459 | 0.5660 | 0.072* | |
H31B | 0.7759 | 0.4732 | 0.4952 | 0.072* | |
C32A | 0.6275 (2) | 0.58260 (19) | 0.51220 (12) | 0.0516 (6) | |
C33A | 0.5586 (3) | 0.6489 (2) | 0.55204 (15) | 0.0765 (8) | |
H33A | 0.5781 | 0.6484 | 0.5914 | 0.092* | |
C34A | 0.4608 (3) | 0.7162 (3) | 0.53455 (18) | 0.0929 (10) | |
H34A | 0.4146 | 0.7607 | 0.5622 | 0.112* | |
C35A | 0.4306 (3) | 0.7184 (3) | 0.47683 (18) | 0.0836 (9) | |
H35A | 0.3642 | 0.7640 | 0.4652 | 0.100* | |
C36A | 0.4990 (3) | 0.6531 (3) | 0.43672 (15) | 0.0734 (8) | |
H36A | 0.4794 | 0.6543 | 0.3973 | 0.088* | |
C37A | 0.5970 (2) | 0.5853 (2) | 0.45399 (13) | 0.0624 (7) | |
H37A | 0.6430 | 0.5410 | 0.4262 | 0.075* | |
C38A | 0.8748 (3) | 0.9421 (2) | 0.59184 (13) | 0.0638 (7) | |
C39A | 0.9931 (3) | 0.9685 (2) | 0.58453 (16) | 0.0804 (9) | |
H39A | 0.9974 | 1.0385 | 0.5572 | 0.121* | |
H39B | 1.0507 | 0.9153 | 0.5651 | 0.121* | |
H39C | 1.0072 | 0.9688 | 0.6265 | 0.121* | |
Cl1A | 1.50042 (6) | 0.38930 (7) | 0.76315 (5) | 0.0968 (3) | |
N1A | 0.80898 (16) | 0.55230 (15) | 0.55602 (9) | 0.0488 (5) | |
N2A | 0.85284 (16) | 0.84018 (14) | 0.62867 (9) | 0.0489 (5) | |
O1A | 0.80457 (14) | 0.44398 (13) | 0.65754 (8) | 0.0564 (4) | |
O2A | 1.03345 (12) | 0.51722 (12) | 0.63662 (7) | 0.0482 (4) | |
O3A | 1.03435 (14) | 0.76046 (12) | 0.65277 (9) | 0.0587 (4) | |
O4A | 0.79804 (19) | 1.00424 (16) | 0.56870 (11) | 0.0931 (7) | |
C1B | 0.1285 (2) | 0.8710 (2) | 0.99801 (12) | 0.0544 (6) | |
C2B | 0.1175 (2) | 0.8145 (2) | 1.06129 (13) | 0.0723 (8) | |
H2B | 0.1552 | 0.8287 | 1.0907 | 0.087* | |
C3B | 0.0485 (3) | 0.7365 (3) | 1.07879 (17) | 0.0890 (10) | |
H3B | 0.0408 | 0.6958 | 1.1208 | 0.107* | |
C4B | −0.0094 (3) | 0.7168 (3) | 1.03644 (18) | 0.0924 (11) | |
H4B | −0.0577 | 0.6651 | 1.0506 | 0.111* | |
C5B | 0.0030 (2) | 0.7731 (2) | 0.97250 (15) | 0.0716 (8) | |
H5B | −0.0363 | 0.7596 | 0.9436 | 0.086* | |
C6B | 0.07510 (19) | 0.84921 (19) | 0.95315 (12) | 0.0514 (6) | |
C8B | 0.16716 (18) | 1.00184 (19) | 0.90820 (12) | 0.0462 (5) | |
C7B | 0.10357 (18) | 0.92456 (18) | 0.88946 (11) | 0.0445 (5) | |
C9B | 0.03217 (18) | 1.02835 (18) | 0.79990 (11) | 0.0462 (5) | |
H9B | 0.0613 | 1.0950 | 0.7970 | 0.055* | |
C10B | 0.13107 (17) | 0.94606 (17) | 0.77017 (11) | 0.0430 (5) | |
H10B | 0.0927 | 0.8986 | 0.7558 | 0.052* | |
C11B | 0.18419 (18) | 0.87469 (17) | 0.82947 (11) | 0.0442 (5) | |
C12B | 0.31239 (18) | 0.85458 (19) | 0.83126 (11) | 0.0461 (5) | |
C13B | 0.39071 (19) | 0.9242 (2) | 0.81823 (12) | 0.0558 (6) | |
H13B | 0.3678 | 0.9978 | 0.8037 | 0.067* | |
C14B | 0.5039 (2) | 0.8837 (3) | 0.82698 (13) | 0.0696 (8) | |
H14B | 0.5568 | 0.9307 | 0.8186 | 0.083* | |
C15B | 0.5392 (2) | 0.7755 (3) | 0.84773 (14) | 0.0778 (9) | |
H15B | 0.6159 | 0.7502 | 0.8529 | 0.093* | |
C16B | 0.4635 (2) | 0.7034 (3) | 0.86102 (13) | 0.0713 (8) | |
H16B | 0.4873 | 0.6299 | 0.8753 | 0.086* | |
C17B | 0.3498 (2) | 0.7447 (2) | 0.85224 (11) | 0.0534 (6) | |
C18B | 0.1613 (2) | 0.75917 (19) | 0.83921 (12) | 0.0519 (6) | |
C19B | 0.20961 (18) | 0.99593 (19) | 0.70979 (12) | 0.0489 (6) | |
C20B | 0.2531 (2) | 1.0889 (2) | 0.70607 (14) | 0.0632 (7) | |
H20B | 0.2387 | 1.1194 | 0.7427 | 0.076* | |
C21B | 0.3172 (2) | 1.1365 (3) | 0.64903 (17) | 0.0826 (10) | |
H21B | 0.3473 | 1.1977 | 0.6477 | 0.099* | |
C22B | 0.3369 (3) | 1.0942 (3) | 0.59424 (18) | 0.0938 (12) | |
H22B | 0.3788 | 1.1276 | 0.5555 | 0.113* | |
C23B | 0.2947 (3) | 1.0023 (3) | 0.59645 (15) | 0.0875 (10) | |
H23B | 0.3081 | 0.9733 | 0.5593 | 0.105* | |
C24B | 0.2318 (2) | 0.9528 (2) | 0.65447 (13) | 0.0630 (7) | |
H24B | 0.2044 | 0.8900 | 0.6561 | 0.076* | |
C25B | −0.07591 (18) | 1.05487 (18) | 0.77123 (11) | 0.0436 (5) | |
C26B | −0.1233 (2) | 1.16007 (19) | 0.74854 (12) | 0.0522 (6) | |
H26B | −0.0862 | 1.2156 | 0.7498 | 0.063* | |
C27B | −0.2248 (2) | 1.1850 (2) | 0.72392 (12) | 0.0581 (6) | |
H27B | −0.2554 | 1.2565 | 0.7083 | 0.070* | |
C28B | −0.27922 (19) | 1.1030 (2) | 0.72300 (11) | 0.0512 (6) | |
C29B | −0.23372 (19) | 0.99666 (19) | 0.74473 (12) | 0.0508 (6) | |
H29B | −0.2708 | 0.9415 | 0.7429 | 0.061* | |
C30B | −0.13283 (18) | 0.97298 (18) | 0.76913 (11) | 0.0496 (6) | |
H30B | −0.1023 | 0.9014 | 0.7844 | 0.060* | |
C31B | 0.2493 (2) | 1.0051 (2) | 1.00396 (13) | 0.0656 (7) | |
H31C | 0.1953 | 1.0299 | 1.0407 | 0.079* | |
H31D | 0.2784 | 1.0674 | 0.9751 | 0.079* | |
C32B | 0.3500 (2) | 0.9261 (2) | 1.02815 (12) | 0.0603 (7) | |
C33B | 0.4081 (2) | 0.8409 (3) | 0.99891 (14) | 0.0771 (9) | |
H33B | 0.3847 | 0.8306 | 0.9629 | 0.093* | |
C34B | 0.5005 (3) | 0.7704 (3) | 1.02169 (15) | 0.0859 (10) | |
H34B | 0.5383 | 0.7132 | 1.0012 | 0.103* | |
C35B | 0.5362 (3) | 0.7842 (3) | 1.07383 (17) | 0.0929 (10) | |
H35B | 0.5989 | 0.7373 | 1.0890 | 0.111* | |
C36B | 0.4795 (4) | 0.8671 (3) | 1.10359 (19) | 0.1157 (14) | |
H36B | 0.5033 | 0.8767 | 1.1396 | 0.139* | |
C37B | 0.3866 (3) | 0.9377 (3) | 1.08115 (16) | 0.0958 (11) | |
H37B | 0.3485 | 0.9939 | 1.1025 | 0.115* | |
C38B | 0.2602 (3) | 0.5761 (2) | 0.88731 (15) | 0.0809 (9) | |
C39B | 0.1573 (4) | 0.5278 (2) | 0.8917 (2) | 0.1152 (13) | |
H39D | 0.1749 | 0.4510 | 0.9062 | 0.173* | |
H39E | 0.1365 | 0.5432 | 0.8497 | 0.173* | |
H39F | 0.0935 | 0.5577 | 0.9220 | 0.173* | |
Cl1B | −0.40960 (6) | 1.13171 (6) | 0.69486 (4) | 0.0808 (2) | |
N1B | 0.18697 (16) | 0.95909 (16) | 0.96957 (9) | 0.0524 (5) | |
N2B | 0.25708 (18) | 0.68690 (15) | 0.85980 (10) | 0.0577 (5) | |
O1B | 0.19531 (14) | 1.08500 (13) | 0.87397 (8) | 0.0559 (4) | |
O2B | 0.00075 (12) | 0.97815 (12) | 0.86691 (7) | 0.0481 (4) | |
O3B | 0.07547 (16) | 0.73540 (14) | 0.82998 (10) | 0.0713 (5) | |
O4B | 0.3451 (3) | 0.52419 (18) | 0.90667 (14) | 0.1253 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1A | 0.0467 (13) | 0.0397 (12) | 0.0541 (15) | 0.0020 (10) | −0.0109 (11) | −0.0130 (11) |
C2A | 0.0650 (17) | 0.0614 (16) | 0.0551 (16) | −0.0001 (14) | −0.0182 (13) | −0.0128 (13) |
C3A | 0.081 (2) | 0.0690 (18) | 0.0521 (16) | −0.0034 (16) | −0.0037 (15) | −0.0101 (14) |
C4A | 0.0603 (17) | 0.0564 (16) | 0.0671 (19) | −0.0079 (13) | 0.0077 (14) | −0.0080 (14) |
C5A | 0.0462 (14) | 0.0462 (14) | 0.0675 (17) | −0.0047 (11) | −0.0033 (12) | −0.0162 (12) |
C6A | 0.0398 (12) | 0.0395 (12) | 0.0535 (14) | 0.0011 (10) | −0.0094 (10) | −0.0129 (10) |
C7A | 0.0353 (11) | 0.0396 (12) | 0.0518 (13) | −0.0009 (9) | −0.0139 (10) | −0.0097 (10) |
C8A | 0.0394 (12) | 0.0348 (12) | 0.0582 (15) | −0.0011 (10) | −0.0144 (11) | −0.0112 (11) |
C9A | 0.0406 (12) | 0.0411 (12) | 0.0617 (15) | −0.0081 (10) | −0.0165 (11) | −0.0058 (11) |
C10A | 0.0391 (12) | 0.0444 (13) | 0.0546 (14) | −0.0068 (10) | −0.0175 (10) | −0.0072 (10) |
C11A | 0.0380 (11) | 0.0381 (12) | 0.0484 (13) | −0.0042 (9) | −0.0129 (10) | −0.0096 (10) |
C12A | 0.0388 (12) | 0.0520 (14) | 0.0452 (13) | −0.0004 (10) | −0.0137 (10) | −0.0172 (11) |
C13A | 0.0424 (13) | 0.0681 (16) | 0.0533 (14) | −0.0076 (12) | −0.0130 (11) | −0.0198 (12) |
C14A | 0.0380 (13) | 0.094 (2) | 0.0611 (16) | −0.0057 (14) | −0.0091 (12) | −0.0362 (16) |
C15A | 0.0429 (15) | 0.085 (2) | 0.082 (2) | 0.0168 (14) | −0.0241 (14) | −0.0426 (17) |
C16A | 0.0553 (16) | 0.0605 (16) | 0.0798 (19) | 0.0101 (13) | −0.0270 (14) | −0.0261 (14) |
C17A | 0.0468 (13) | 0.0494 (14) | 0.0551 (14) | 0.0029 (11) | −0.0179 (11) | −0.0215 (11) |
C18A | 0.0461 (13) | 0.0404 (12) | 0.0512 (14) | −0.0021 (10) | −0.0153 (11) | −0.0129 (10) |
C19A | 0.0400 (13) | 0.0575 (15) | 0.0530 (15) | −0.0002 (11) | −0.0167 (11) | −0.0028 (12) |
C20A | 0.0585 (16) | 0.0788 (19) | 0.0604 (17) | −0.0185 (15) | −0.0190 (13) | 0.0029 (14) |
C21A | 0.0614 (18) | 0.099 (2) | 0.074 (2) | −0.0209 (17) | −0.0163 (16) | 0.0218 (19) |
C22A | 0.061 (2) | 0.129 (3) | 0.060 (2) | 0.004 (2) | −0.0037 (16) | 0.011 (2) |
C23A | 0.074 (2) | 0.113 (3) | 0.064 (2) | 0.010 (2) | −0.0126 (17) | −0.0192 (19) |
C24A | 0.0569 (16) | 0.0734 (18) | 0.0623 (18) | 0.0050 (14) | −0.0160 (14) | −0.0128 (15) |
C25A | 0.0408 (12) | 0.0453 (13) | 0.0588 (15) | −0.0032 (10) | −0.0157 (11) | −0.0075 (11) |
C26A | 0.0503 (14) | 0.0451 (14) | 0.0703 (17) | −0.0049 (11) | −0.0201 (12) | −0.0039 (12) |
C27A | 0.0582 (16) | 0.0526 (15) | 0.0785 (19) | 0.0059 (13) | −0.0318 (14) | −0.0053 (13) |
C28A | 0.0409 (13) | 0.0699 (17) | 0.0696 (17) | 0.0021 (13) | −0.0234 (12) | −0.0188 (14) |
C29A | 0.0466 (15) | 0.0720 (18) | 0.086 (2) | −0.0162 (13) | −0.0235 (14) | −0.0011 (15) |
C30A | 0.0523 (15) | 0.0573 (16) | 0.0827 (19) | −0.0110 (13) | −0.0283 (14) | 0.0084 (14) |
C31A | 0.0619 (16) | 0.0532 (15) | 0.0779 (18) | −0.0051 (12) | −0.0305 (14) | −0.0251 (13) |
C32A | 0.0506 (14) | 0.0502 (14) | 0.0623 (16) | −0.0127 (11) | −0.0217 (12) | −0.0126 (12) |
C33A | 0.0743 (19) | 0.087 (2) | 0.075 (2) | 0.0096 (16) | −0.0323 (16) | −0.0324 (17) |
C34A | 0.074 (2) | 0.101 (3) | 0.105 (3) | 0.0177 (19) | −0.0313 (19) | −0.040 (2) |
C35A | 0.0605 (19) | 0.083 (2) | 0.104 (3) | −0.0077 (17) | −0.0363 (18) | 0.003 (2) |
C36A | 0.072 (2) | 0.085 (2) | 0.0712 (19) | −0.0309 (17) | −0.0362 (16) | 0.0075 (17) |
C37A | 0.0648 (17) | 0.0677 (17) | 0.0636 (17) | −0.0212 (14) | −0.0213 (14) | −0.0117 (13) |
C38A | 0.0729 (19) | 0.0475 (15) | 0.0646 (17) | 0.0028 (14) | −0.0182 (14) | −0.0058 (13) |
C39A | 0.083 (2) | 0.0544 (17) | 0.100 (2) | −0.0212 (15) | −0.0249 (18) | 0.0074 (16) |
Cl1A | 0.0526 (4) | 0.1110 (7) | 0.1330 (8) | 0.0034 (4) | −0.0485 (5) | −0.0215 (6) |
N1A | 0.0483 (11) | 0.0447 (11) | 0.0598 (12) | −0.0067 (9) | −0.0216 (10) | −0.0124 (9) |
N2A | 0.0498 (11) | 0.0375 (10) | 0.0604 (12) | −0.0004 (9) | −0.0182 (9) | −0.0105 (9) |
O1A | 0.0602 (10) | 0.0464 (9) | 0.0659 (11) | −0.0184 (8) | −0.0178 (9) | −0.0034 (8) |
O2A | 0.0393 (8) | 0.0470 (9) | 0.0587 (10) | 0.0021 (7) | −0.0160 (7) | −0.0133 (8) |
O3A | 0.0470 (10) | 0.0472 (9) | 0.0858 (13) | −0.0115 (8) | −0.0256 (9) | −0.0047 (9) |
O4A | 0.0870 (15) | 0.0665 (13) | 0.1068 (17) | 0.0060 (11) | −0.0314 (13) | 0.0155 (12) |
C1B | 0.0414 (13) | 0.0575 (15) | 0.0530 (15) | 0.0058 (11) | −0.0018 (11) | −0.0094 (12) |
C2B | 0.0623 (18) | 0.082 (2) | 0.0549 (17) | 0.0053 (16) | −0.0009 (14) | −0.0061 (15) |
C3B | 0.079 (2) | 0.088 (2) | 0.068 (2) | −0.0018 (19) | 0.0082 (18) | 0.0137 (18) |
C4B | 0.073 (2) | 0.083 (2) | 0.098 (3) | −0.0274 (18) | 0.009 (2) | 0.015 (2) |
C5B | 0.0572 (17) | 0.0668 (18) | 0.083 (2) | −0.0174 (14) | −0.0025 (14) | −0.0031 (15) |
C6B | 0.0364 (12) | 0.0504 (14) | 0.0586 (15) | −0.0030 (10) | −0.0001 (11) | −0.0063 (12) |
C8B | 0.0340 (12) | 0.0482 (14) | 0.0527 (14) | −0.0001 (10) | −0.0052 (10) | −0.0122 (11) |
C7B | 0.0313 (11) | 0.0460 (13) | 0.0534 (14) | −0.0030 (9) | −0.0088 (10) | −0.0066 (10) |
C9B | 0.0347 (11) | 0.0431 (12) | 0.0600 (15) | −0.0067 (10) | −0.0109 (10) | −0.0069 (11) |
C10B | 0.0326 (11) | 0.0432 (12) | 0.0541 (14) | −0.0062 (9) | −0.0124 (10) | −0.0075 (10) |
C11B | 0.0343 (11) | 0.0432 (12) | 0.0535 (14) | −0.0045 (10) | −0.0085 (10) | −0.0081 (10) |
C12B | 0.0367 (12) | 0.0541 (14) | 0.0456 (13) | 0.0007 (11) | −0.0082 (10) | −0.0132 (11) |
C13B | 0.0380 (13) | 0.0734 (17) | 0.0565 (15) | −0.0093 (12) | −0.0079 (11) | −0.0151 (13) |
C14B | 0.0381 (14) | 0.111 (3) | 0.0617 (17) | −0.0110 (15) | −0.0081 (12) | −0.0250 (17) |
C15B | 0.0386 (15) | 0.123 (3) | 0.0653 (18) | 0.0147 (17) | −0.0143 (13) | −0.0280 (19) |
C16B | 0.0593 (17) | 0.083 (2) | 0.0607 (17) | 0.0262 (16) | −0.0164 (14) | −0.0227 (15) |
C17B | 0.0493 (14) | 0.0601 (16) | 0.0468 (14) | 0.0074 (12) | −0.0112 (11) | −0.0164 (12) |
C18B | 0.0534 (15) | 0.0455 (14) | 0.0568 (15) | −0.0086 (12) | −0.0096 (12) | −0.0105 (11) |
C19B | 0.0310 (11) | 0.0537 (14) | 0.0566 (15) | 0.0003 (10) | −0.0136 (10) | −0.0020 (12) |
C20B | 0.0480 (14) | 0.0642 (17) | 0.0723 (18) | −0.0168 (13) | −0.0158 (13) | 0.0075 (14) |
C21B | 0.0567 (18) | 0.087 (2) | 0.089 (2) | −0.0215 (16) | −0.0164 (17) | 0.0225 (19) |
C22B | 0.0575 (19) | 0.113 (3) | 0.075 (2) | −0.0058 (19) | −0.0032 (17) | 0.032 (2) |
C23B | 0.068 (2) | 0.113 (3) | 0.0580 (19) | 0.013 (2) | −0.0049 (16) | −0.0043 (19) |
C24B | 0.0451 (14) | 0.0723 (18) | 0.0640 (18) | 0.0039 (13) | −0.0122 (13) | −0.0096 (14) |
C25B | 0.0320 (11) | 0.0451 (13) | 0.0507 (13) | −0.0064 (10) | −0.0061 (10) | −0.0057 (10) |
C26B | 0.0461 (13) | 0.0445 (13) | 0.0631 (16) | −0.0083 (11) | −0.0108 (11) | −0.0039 (11) |
C27B | 0.0521 (15) | 0.0465 (14) | 0.0681 (17) | 0.0000 (12) | −0.0198 (13) | 0.0037 (12) |
C28B | 0.0389 (12) | 0.0608 (15) | 0.0526 (14) | −0.0015 (11) | −0.0159 (11) | −0.0078 (12) |
C29B | 0.0387 (12) | 0.0527 (14) | 0.0623 (15) | −0.0084 (11) | −0.0095 (11) | −0.0132 (12) |
C30B | 0.0373 (12) | 0.0443 (13) | 0.0633 (15) | −0.0016 (10) | −0.0125 (11) | −0.0049 (11) |
C31B | 0.0646 (17) | 0.0757 (18) | 0.0629 (17) | −0.0010 (14) | −0.0204 (14) | −0.0281 (14) |
C32B | 0.0542 (15) | 0.0765 (18) | 0.0508 (15) | −0.0074 (13) | −0.0111 (12) | −0.0159 (13) |
C33B | 0.0612 (17) | 0.109 (2) | 0.0623 (18) | 0.0100 (17) | −0.0193 (14) | −0.0342 (17) |
C34B | 0.0664 (19) | 0.107 (3) | 0.077 (2) | 0.0147 (18) | −0.0153 (16) | −0.0298 (19) |
C35B | 0.080 (2) | 0.113 (3) | 0.082 (2) | 0.007 (2) | −0.0353 (19) | −0.012 (2) |
C36B | 0.135 (3) | 0.129 (3) | 0.103 (3) | 0.020 (3) | −0.080 (3) | −0.041 (3) |
C37B | 0.109 (3) | 0.107 (3) | 0.084 (2) | 0.015 (2) | −0.050 (2) | −0.044 (2) |
C38B | 0.111 (3) | 0.0450 (16) | 0.079 (2) | 0.0057 (18) | −0.0242 (19) | −0.0091 (15) |
C39B | 0.149 (4) | 0.0457 (18) | 0.149 (4) | −0.028 (2) | −0.036 (3) | 0.004 (2) |
Cl1B | 0.0626 (4) | 0.0850 (5) | 0.1025 (6) | 0.0078 (4) | −0.0497 (4) | −0.0183 (4) |
N1B | 0.0488 (11) | 0.0582 (12) | 0.0500 (12) | −0.0047 (10) | −0.0114 (9) | −0.0126 (10) |
N2B | 0.0654 (14) | 0.0411 (11) | 0.0625 (13) | 0.0052 (10) | −0.0158 (11) | −0.0115 (10) |
O1B | 0.0543 (10) | 0.0505 (10) | 0.0645 (11) | −0.0118 (8) | −0.0152 (8) | −0.0080 (9) |
O2B | 0.0320 (8) | 0.0540 (9) | 0.0550 (10) | −0.0021 (7) | −0.0088 (7) | −0.0088 (8) |
O3B | 0.0699 (12) | 0.0534 (11) | 0.0984 (15) | −0.0225 (9) | −0.0290 (11) | −0.0065 (10) |
O4B | 0.139 (2) | 0.0637 (14) | 0.156 (2) | 0.0175 (15) | −0.059 (2) | 0.0095 (15) |
C1A—C2A | 1.372 (3) | C1B—C2B | 1.378 (4) |
C1A—C6A | 1.383 (3) | C1B—C6B | 1.386 (3) |
C1A—N1A | 1.416 (3) | C1B—N1B | 1.406 (3) |
C2A—C3A | 1.378 (4) | C2B—C3B | 1.370 (4) |
C2A—H2A | 0.9300 | C2B—H2B | 0.9300 |
C3A—C4A | 1.375 (4) | C3B—C4B | 1.364 (5) |
C3A—H3A | 0.9300 | C3B—H3B | 0.9300 |
C4A—C5A | 1.386 (4) | C4B—C5B | 1.389 (4) |
C4A—H4A | 0.9300 | C4B—H4B | 0.9300 |
C5A—C6A | 1.380 (3) | C5B—C6B | 1.376 (3) |
C5A—H5A | 0.9300 | C5B—H5B | 0.9300 |
C6A—C7A | 1.506 (3) | C6B—C7B | 1.498 (3) |
C7A—O2A | 1.407 (2) | C8B—O1B | 1.216 (3) |
C7A—C8A | 1.557 (3) | C8B—N1B | 1.363 (3) |
C7A—C11A | 1.592 (3) | C8B—C7B | 1.551 (3) |
C8A—O1A | 1.210 (3) | C7B—O2B | 1.409 (2) |
C8A—N1A | 1.364 (3) | C7B—C11B | 1.602 (3) |
C9A—O2A | 1.437 (3) | C9B—O2B | 1.435 (3) |
C9A—C25A | 1.509 (3) | C9B—C25B | 1.503 (3) |
C9A—C10A | 1.553 (3) | C9B—C10B | 1.540 (3) |
C9A—H9A | 0.9800 | C9B—H9B | 0.9800 |
C10A—C19A | 1.511 (3) | C10B—C19B | 1.513 (3) |
C10A—C11A | 1.574 (3) | C10B—C11B | 1.569 (3) |
C10A—H10A | 0.9800 | C10B—H10B | 0.9800 |
C11A—C12A | 1.514 (3) | C11B—C12B | 1.510 (3) |
C11A—C18A | 1.537 (3) | C11B—C18B | 1.533 (3) |
C12A—C13A | 1.383 (3) | C12B—C13B | 1.375 (3) |
C12A—C17A | 1.391 (3) | C12B—C17B | 1.392 (3) |
C13A—C14A | 1.385 (3) | C13B—C14B | 1.384 (3) |
C13A—H13A | 0.9300 | C13B—H13B | 0.9300 |
C14A—C15A | 1.369 (4) | C14B—C15B | 1.369 (4) |
C14A—H14A | 0.9300 | C14B—H14B | 0.9300 |
C15A—C16A | 1.380 (4) | C15B—C16B | 1.375 (4) |
C15A—H15A | 0.9300 | C15B—H15B | 0.9300 |
C16A—C17A | 1.382 (3) | C16B—C17B | 1.390 (3) |
C16A—H16A | 0.9300 | C16B—H16B | 0.9300 |
C17A—N2A | 1.428 (3) | C17B—N2B | 1.427 (3) |
C18A—O3A | 1.204 (3) | C18B—O3B | 1.206 (3) |
C18A—N2A | 1.396 (3) | C18B—N2B | 1.402 (3) |
C19A—C24A | 1.381 (4) | C19B—C24B | 1.381 (3) |
C19A—C20A | 1.387 (4) | C19B—C20B | 1.388 (3) |
C20A—C21A | 1.382 (4) | C20B—C21B | 1.373 (4) |
C20A—H20A | 0.9300 | C20B—H20B | 0.9300 |
C21A—C22A | 1.374 (5) | C21B—C22B | 1.368 (5) |
C21A—H21A | 0.9300 | C21B—H21B | 0.9300 |
C22A—C23A | 1.364 (5) | C22B—C23B | 1.375 (5) |
C22A—H22A | 0.9300 | C22B—H22B | 0.9300 |
C23A—C24A | 1.386 (4) | C23B—C24B | 1.390 (4) |
C23A—H23A | 0.9300 | C23B—H23B | 0.9300 |
C24A—H24A | 0.9300 | C24B—H24B | 0.9300 |
C25A—C26A | 1.375 (3) | C25B—C26B | 1.376 (3) |
C25A—C30A | 1.385 (3) | C25B—C30B | 1.391 (3) |
C26A—C27A | 1.382 (3) | C26B—C27B | 1.385 (3) |
C26A—H26A | 0.9300 | C26B—H26B | 0.9300 |
C27A—C28A | 1.367 (4) | C27B—C28B | 1.366 (3) |
C27A—H27A | 0.9300 | C27B—H27B | 0.9300 |
C28A—C29A | 1.367 (4) | C28B—C29B | 1.377 (3) |
C28A—Cl1A | 1.738 (2) | C28B—Cl1B | 1.741 (2) |
C29A—C30A | 1.375 (3) | C29B—C30B | 1.376 (3) |
C29A—H29A | 0.9300 | C29B—H29B | 0.9300 |
C30A—H30A | 0.9300 | C30B—H30B | 0.9300 |
C31A—N1A | 1.458 (3) | C31B—N1B | 1.456 (3) |
C31A—C32A | 1.508 (3) | C31B—C32B | 1.511 (4) |
C31A—H31A | 0.9700 | C31B—H31C | 0.9700 |
C31A—H31B | 0.9700 | C31B—H31D | 0.9700 |
C32A—C33A | 1.366 (4) | C32B—C37B | 1.365 (4) |
C32A—C37A | 1.378 (3) | C32B—C33B | 1.374 (4) |
C33A—C34A | 1.372 (4) | C33B—C34B | 1.380 (4) |
C33A—H33A | 0.9300 | C33B—H33B | 0.9300 |
C34A—C35A | 1.367 (4) | C34B—C35B | 1.353 (4) |
C34A—H34A | 0.9300 | C34B—H34B | 0.9300 |
C35A—C36A | 1.360 (4) | C35B—C36B | 1.353 (5) |
C35A—H35A | 0.9300 | C35B—H35B | 0.9300 |
C36A—C37A | 1.375 (4) | C36B—C37B | 1.382 (4) |
C36A—H36A | 0.9300 | C36B—H36B | 0.9300 |
C37A—H37A | 0.9300 | C37B—H37B | 0.9300 |
C38A—O4A | 1.203 (3) | C38B—O4B | 1.196 (4) |
C38A—N2A | 1.412 (3) | C38B—N2B | 1.410 (3) |
C38A—C39A | 1.492 (4) | C38B—C39B | 1.473 (5) |
C39A—H39A | 0.9600 | C39B—H39D | 0.9600 |
C39A—H39B | 0.9600 | C39B—H39E | 0.9600 |
C39A—H39C | 0.9600 | C39B—H39F | 0.9600 |
C2A—C1A—C6A | 122.5 (2) | C2B—C1B—C6B | 122.2 (3) |
C2A—C1A—N1A | 127.4 (2) | C2B—C1B—N1B | 127.8 (3) |
C6A—C1A—N1A | 110.0 (2) | C6B—C1B—N1B | 109.9 (2) |
C1A—C2A—C3A | 117.2 (3) | C3B—C2B—C1B | 116.9 (3) |
C1A—C2A—H2A | 121.4 | C3B—C2B—H2B | 121.5 |
C3A—C2A—H2A | 121.4 | C1B—C2B—H2B | 121.5 |
C4A—C3A—C2A | 121.7 (3) | C4B—C3B—C2B | 122.0 (3) |
C4A—C3A—H3A | 119.1 | C4B—C3B—H3B | 119.0 |
C2A—C3A—H3A | 119.1 | C2B—C3B—H3B | 119.0 |
C3A—C4A—C5A | 120.3 (3) | C3B—C4B—C5B | 120.9 (3) |
C3A—C4A—H4A | 119.9 | C3B—C4B—H4B | 119.6 |
C5A—C4A—H4A | 119.9 | C5B—C4B—H4B | 119.6 |
C6A—C5A—C4A | 118.8 (2) | C6B—C5B—C4B | 118.1 (3) |
C6A—C5A—H5A | 120.6 | C6B—C5B—H5B | 120.9 |
C4A—C5A—H5A | 120.6 | C4B—C5B—H5B | 120.9 |
C5A—C6A—C1A | 119.4 (2) | C5B—C6B—C1B | 119.7 (2) |
C5A—C6A—C7A | 131.4 (2) | C5B—C6B—C7B | 131.1 (2) |
C1A—C6A—C7A | 108.99 (19) | C1B—C6B—C7B | 109.1 (2) |
O2A—C7A—C6A | 110.20 (17) | O1B—C8B—N1B | 126.2 (2) |
O2A—C7A—C8A | 112.65 (17) | O1B—C8B—C7B | 126.1 (2) |
C6A—C7A—C8A | 101.65 (17) | N1B—C8B—C7B | 107.7 (2) |
O2A—C7A—C11A | 104.67 (16) | O2B—C7B—C6B | 110.33 (17) |
C6A—C7A—C11A | 117.65 (17) | O2B—C7B—C8B | 112.77 (17) |
C8A—C7A—C11A | 110.29 (17) | C6B—C7B—C8B | 101.62 (19) |
O1A—C8A—N1A | 126.4 (2) | O2B—C7B—C11B | 104.57 (17) |
O1A—C8A—C7A | 125.9 (2) | C6B—C7B—C11B | 118.19 (18) |
N1A—C8A—C7A | 107.66 (19) | C8B—C7B—C11B | 109.63 (17) |
O2A—C9A—C25A | 106.33 (18) | O2B—C9B—C25B | 107.40 (17) |
O2A—C9A—C10A | 105.92 (17) | O2B—C9B—C10B | 104.99 (17) |
C25A—C9A—C10A | 115.45 (18) | C25B—C9B—C10B | 115.38 (19) |
O2A—C9A—H9A | 109.6 | O2B—C9B—H9B | 109.6 |
C25A—C9A—H9A | 109.6 | C25B—C9B—H9B | 109.6 |
C10A—C9A—H9A | 109.6 | C10B—C9B—H9B | 109.6 |
C19A—C10A—C9A | 114.50 (19) | C19B—C10B—C9B | 113.86 (18) |
C19A—C10A—C11A | 119.29 (17) | C19B—C10B—C11B | 120.18 (17) |
C9A—C10A—C11A | 104.63 (17) | C9B—C10B—C11B | 104.63 (18) |
C19A—C10A—H10A | 105.8 | C19B—C10B—H10B | 105.7 |
C9A—C10A—H10A | 105.8 | C9B—C10B—H10B | 105.7 |
C11A—C10A—H10A | 105.8 | C11B—C10B—H10B | 105.7 |
C12A—C11A—C18A | 101.36 (17) | C12B—C11B—C18B | 101.40 (18) |
C12A—C11A—C10A | 123.25 (18) | C12B—C11B—C10B | 123.37 (18) |
C18A—C11A—C10A | 108.93 (17) | C18B—C11B—C10B | 108.78 (18) |
C12A—C11A—C7A | 113.36 (16) | C12B—C11B—C7B | 113.20 (18) |
C18A—C11A—C7A | 105.98 (17) | C18B—C11B—C7B | 106.75 (17) |
C10A—C11A—C7A | 102.92 (16) | C10B—C11B—C7B | 102.47 (16) |
C13A—C12A—C17A | 119.4 (2) | C13B—C12B—C17B | 118.8 (2) |
C13A—C12A—C11A | 131.6 (2) | C13B—C12B—C11B | 131.5 (2) |
C17A—C12A—C11A | 108.97 (19) | C17B—C12B—C11B | 109.6 (2) |
C12A—C13A—C14A | 118.8 (2) | C12B—C13B—C14B | 119.4 (3) |
C12A—C13A—H13A | 120.6 | C12B—C13B—H13B | 120.3 |
C14A—C13A—H13A | 120.6 | C14B—C13B—H13B | 120.3 |
C15A—C14A—C13A | 120.8 (3) | C15B—C14B—C13B | 121.0 (3) |
C15A—C14A—H14A | 119.6 | C15B—C14B—H14B | 119.5 |
C13A—C14A—H14A | 119.6 | C13B—C14B—H14B | 119.5 |
C14A—C15A—C16A | 121.7 (2) | C14B—C15B—C16B | 121.2 (3) |
C14A—C15A—H15A | 119.1 | C14B—C15B—H15B | 119.4 |
C16A—C15A—H15A | 119.1 | C16B—C15B—H15B | 119.4 |
C15A—C16A—C17A | 117.1 (3) | C15B—C16B—C17B | 117.4 (3) |
C15A—C16A—H16A | 121.4 | C15B—C16B—H16B | 121.3 |
C17A—C16A—H16A | 121.4 | C17B—C16B—H16B | 121.3 |
C16A—C17A—C12A | 122.1 (2) | C16B—C17B—C12B | 122.1 (3) |
C16A—C17A—N2A | 127.6 (2) | C16B—C17B—N2B | 128.1 (2) |
C12A—C17A—N2A | 110.08 (19) | C12B—C17B—N2B | 109.7 (2) |
O3A—C18A—N2A | 126.0 (2) | O3B—C18B—N2B | 126.2 (2) |
O3A—C18A—C11A | 125.6 (2) | O3B—C18B—C11B | 125.2 (2) |
N2A—C18A—C11A | 108.41 (18) | N2B—C18B—C11B | 108.6 (2) |
C24A—C19A—C20A | 117.7 (2) | C24B—C19B—C20B | 118.2 (2) |
C24A—C19A—C10A | 119.0 (2) | C24B—C19B—C10B | 119.1 (2) |
C20A—C19A—C10A | 123.3 (2) | C20B—C19B—C10B | 122.5 (2) |
C21A—C20A—C19A | 121.0 (3) | C21B—C20B—C19B | 121.0 (3) |
C21A—C20A—H20A | 119.5 | C21B—C20B—H20B | 119.5 |
C19A—C20A—H20A | 119.5 | C19B—C20B—H20B | 119.5 |
C22A—C21A—C20A | 120.0 (3) | C22B—C21B—C20B | 120.3 (3) |
C22A—C21A—H21A | 120.0 | C22B—C21B—H21B | 119.9 |
C20A—C21A—H21A | 120.0 | C20B—C21B—H21B | 119.9 |
C23A—C22A—C21A | 120.0 (3) | C21B—C22B—C23B | 120.0 (3) |
C23A—C22A—H22A | 120.0 | C21B—C22B—H22B | 120.0 |
C21A—C22A—H22A | 120.0 | C23B—C22B—H22B | 120.0 |
C22A—C23A—C24A | 119.9 (3) | C22B—C23B—C24B | 119.8 (3) |
C22A—C23A—H23A | 120.0 | C22B—C23B—H23B | 120.1 |
C24A—C23A—H23A | 120.0 | C24B—C23B—H23B | 120.1 |
C19A—C24A—C23A | 121.4 (3) | C19B—C24B—C23B | 120.7 (3) |
C19A—C24A—H24A | 119.3 | C19B—C24B—H24B | 119.7 |
C23A—C24A—H24A | 119.3 | C23B—C24B—H24B | 119.7 |
C26A—C25A—C30A | 118.1 (2) | C26B—C25B—C30B | 118.4 (2) |
C26A—C25A—C9A | 122.4 (2) | C26B—C25B—C9B | 121.3 (2) |
C30A—C25A—C9A | 119.5 (2) | C30B—C25B—C9B | 120.35 (19) |
C25A—C26A—C27A | 121.4 (2) | C25B—C26B—C27B | 121.4 (2) |
C25A—C26A—H26A | 119.3 | C25B—C26B—H26B | 119.3 |
C27A—C26A—H26A | 119.3 | C27B—C26B—H26B | 119.3 |
C28A—C27A—C26A | 119.1 (2) | C28B—C27B—C26B | 118.9 (2) |
C28A—C27A—H27A | 120.4 | C28B—C27B—H27B | 120.6 |
C26A—C27A—H27A | 120.4 | C26B—C27B—H27B | 120.6 |
C27A—C28A—C29A | 120.9 (2) | C27B—C28B—C29B | 121.3 (2) |
C27A—C28A—Cl1A | 120.7 (2) | C27B—C28B—Cl1B | 120.08 (18) |
C29A—C28A—Cl1A | 118.4 (2) | C29B—C28B—Cl1B | 118.65 (19) |
C28A—C29A—C30A | 119.5 (3) | C30B—C29B—C28B | 119.3 (2) |
C28A—C29A—H29A | 120.2 | C30B—C29B—H29B | 120.4 |
C30A—C29A—H29A | 120.2 | C28B—C29B—H29B | 120.4 |
C29A—C30A—C25A | 121.0 (2) | C29B—C30B—C25B | 120.8 (2) |
C29A—C30A—H30A | 119.5 | C29B—C30B—H30B | 119.6 |
C25A—C30A—H30A | 119.5 | C25B—C30B—H30B | 119.6 |
N1A—C31A—C32A | 114.10 (19) | N1B—C31B—C32B | 113.2 (2) |
N1A—C31A—H31A | 108.7 | N1B—C31B—H31C | 108.9 |
C32A—C31A—H31A | 108.7 | C32B—C31B—H31C | 108.9 |
N1A—C31A—H31B | 108.7 | N1B—C31B—H31D | 108.9 |
C32A—C31A—H31B | 108.7 | C32B—C31B—H31D | 108.9 |
H31A—C31A—H31B | 107.6 | H31C—C31B—H31D | 107.8 |
C33A—C32A—C37A | 118.5 (2) | C37B—C32B—C33B | 117.3 (3) |
C33A—C32A—C31A | 121.3 (2) | C37B—C32B—C31B | 120.1 (3) |
C37A—C32A—C31A | 120.2 (2) | C33B—C32B—C31B | 122.6 (2) |
C32A—C33A—C34A | 120.6 (3) | C32B—C33B—C34B | 121.5 (3) |
C32A—C33A—H33A | 119.7 | C32B—C33B—H33B | 119.3 |
C34A—C33A—H33A | 119.7 | C34B—C33B—H33B | 119.3 |
C35A—C34A—C33A | 120.7 (3) | C35B—C34B—C33B | 120.2 (3) |
C35A—C34A—H34A | 119.7 | C35B—C34B—H34B | 119.9 |
C33A—C34A—H34A | 119.7 | C33B—C34B—H34B | 119.9 |
C36A—C35A—C34A | 119.1 (3) | C36B—C35B—C34B | 119.2 (3) |
C36A—C35A—H35A | 120.5 | C36B—C35B—H35B | 120.4 |
C34A—C35A—H35A | 120.5 | C34B—C35B—H35B | 120.4 |
C35A—C36A—C37A | 120.6 (3) | C35B—C36B—C37B | 120.9 (3) |
C35A—C36A—H36A | 119.7 | C35B—C36B—H36B | 119.6 |
C37A—C36A—H36A | 119.7 | C37B—C36B—H36B | 119.6 |
C36A—C37A—C32A | 120.5 (3) | C32B—C37B—C36B | 121.0 (3) |
C36A—C37A—H37A | 119.7 | C32B—C37B—H37B | 119.5 |
C32A—C37A—H37A | 119.7 | C36B—C37B—H37B | 119.5 |
O4A—C38A—N2A | 119.2 (3) | O4B—C38B—N2B | 119.7 (3) |
O4A—C38A—C39A | 122.9 (3) | O4B—C38B—C39B | 121.8 (3) |
N2A—C38A—C39A | 117.9 (2) | N2B—C38B—C39B | 118.5 (3) |
C38A—C39A—H39A | 109.5 | C38B—C39B—H39D | 109.5 |
C38A—C39A—H39B | 109.5 | C38B—C39B—H39E | 109.5 |
H39A—C39A—H39B | 109.5 | H39D—C39B—H39E | 109.5 |
C38A—C39A—H39C | 109.5 | C38B—C39B—H39F | 109.5 |
H39A—C39A—H39C | 109.5 | H39D—C39B—H39F | 109.5 |
H39B—C39A—H39C | 109.5 | H39E—C39B—H39F | 109.5 |
C8A—N1A—C1A | 110.79 (18) | C8B—N1B—C1B | 110.8 (2) |
C8A—N1A—C31A | 124.2 (2) | C8B—N1B—C31B | 124.8 (2) |
C1A—N1A—C31A | 123.5 (2) | C1B—N1B—C31B | 124.1 (2) |
C18A—N2A—C38A | 125.8 (2) | C18B—N2B—C38B | 126.1 (2) |
C18A—N2A—C17A | 108.95 (18) | C18B—N2B—C17B | 109.00 (19) |
C38A—N2A—C17A | 125.2 (2) | C38B—N2B—C17B | 124.8 (2) |
C7A—O2A—C9A | 109.86 (16) | C7B—O2B—C9B | 108.24 (15) |
C6A—C1A—C2A—C3A | 2.3 (4) | C6B—C1B—C2B—C3B | −1.5 (4) |
N1A—C1A—C2A—C3A | −173.7 (2) | N1B—C1B—C2B—C3B | 175.2 (2) |
C1A—C2A—C3A—C4A | 1.3 (4) | C1B—C2B—C3B—C4B | −1.6 (5) |
C2A—C3A—C4A—C5A | −3.0 (4) | C2B—C3B—C4B—C5B | 2.4 (5) |
C3A—C4A—C5A—C6A | 1.2 (4) | C3B—C4B—C5B—C6B | −0.1 (5) |
C4A—C5A—C6A—C1A | 2.2 (3) | C4B—C5B—C6B—C1B | −2.9 (4) |
C4A—C5A—C6A—C7A | 176.5 (2) | C4B—C5B—C6B—C7B | −177.8 (3) |
C2A—C1A—C6A—C5A | −4.1 (3) | C2B—C1B—C6B—C5B | 3.8 (4) |
N1A—C1A—C6A—C5A | 172.52 (19) | N1B—C1B—C6B—C5B | −173.4 (2) |
C2A—C1A—C6A—C7A | −179.6 (2) | C2B—C1B—C6B—C7B | 179.8 (2) |
N1A—C1A—C6A—C7A | −3.0 (2) | N1B—C1B—C6B—C7B | 2.5 (3) |
C5A—C6A—C7A—O2A | −47.7 (3) | C5B—C6B—C7B—O2B | 48.2 (3) |
C1A—C6A—C7A—O2A | 127.10 (18) | C1B—C6B—C7B—O2B | −127.1 (2) |
C5A—C6A—C7A—C8A | −167.3 (2) | C5B—C6B—C7B—C8B | 168.0 (2) |
C1A—C6A—C7A—C8A | 7.4 (2) | C1B—C6B—C7B—C8B | −7.3 (2) |
C5A—C6A—C7A—C11A | 72.2 (3) | C5B—C6B—C7B—C11B | −72.0 (3) |
C1A—C6A—C7A—C11A | −113.1 (2) | C1B—C6B—C7B—C11B | 112.7 (2) |
O2A—C7A—C8A—O1A | 51.9 (3) | O1B—C8B—C7B—O2B | −52.8 (3) |
C6A—C7A—C8A—O1A | 169.8 (2) | N1B—C8B—C7B—O2B | 127.95 (19) |
C11A—C7A—C8A—O1A | −64.7 (3) | O1B—C8B—C7B—C6B | −170.9 (2) |
O2A—C7A—C8A—N1A | −127.49 (19) | N1B—C8B—C7B—C6B | 9.9 (2) |
C6A—C7A—C8A—N1A | −9.6 (2) | O1B—C8B—C7B—C11B | 63.3 (3) |
C11A—C7A—C8A—N1A | 115.97 (19) | N1B—C8B—C7B—C11B | −115.99 (19) |
O2A—C9A—C10A—C19A | 146.77 (18) | O2B—C9B—C10B—C19B | −156.53 (17) |
C25A—C9A—C10A—C19A | −95.9 (2) | C25B—C9B—C10B—C19B | 85.5 (2) |
O2A—C9A—C10A—C11A | 14.3 (2) | O2B—C9B—C10B—C11B | −23.4 (2) |
C25A—C9A—C10A—C11A | 131.70 (19) | C25B—C9B—C10B—C11B | −141.41 (18) |
C19A—C10A—C11A—C12A | 5.8 (3) | C19B—C10B—C11B—C12B | 2.1 (3) |
C9A—C10A—C11A—C12A | 135.4 (2) | C9B—C10B—C11B—C12B | −127.4 (2) |
C19A—C10A—C11A—C18A | 124.1 (2) | C19B—C10B—C11B—C18B | −116.2 (2) |
C9A—C10A—C11A—C18A | −106.30 (19) | C9B—C10B—C11B—C18B | 114.32 (19) |
C19A—C10A—C11A—C7A | −123.8 (2) | C19B—C10B—C11B—C7B | 131.0 (2) |
C9A—C10A—C11A—C7A | 5.9 (2) | C9B—C10B—C11B—C7B | 1.6 (2) |
O2A—C7A—C11A—C12A | −160.03 (17) | O2B—C7B—C11B—C12B | 156.15 (17) |
C6A—C7A—C11A—C12A | 77.3 (2) | C6B—C7B—C11B—C12B | −80.7 (2) |
C8A—C7A—C11A—C12A | −38.6 (2) | C8B—C7B—C11B—C12B | 35.0 (2) |
O2A—C7A—C11A—C18A | 89.68 (18) | O2B—C7B—C11B—C18B | −93.15 (19) |
C6A—C7A—C11A—C18A | −33.0 (2) | C6B—C7B—C11B—C18B | 30.0 (3) |
C8A—C7A—C11A—C18A | −148.91 (17) | C8B—C7B—C11B—C18B | 145.70 (19) |
O2A—C7A—C11A—C10A | −24.6 (2) | O2B—C7B—C11B—C10B | 21.1 (2) |
C6A—C7A—C11A—C10A | −147.34 (18) | C6B—C7B—C11B—C10B | 144.23 (19) |
C8A—C7A—C11A—C10A | 96.76 (19) | C8B—C7B—C11B—C10B | −100.05 (19) |
C18A—C11A—C12A—C13A | −169.1 (2) | C18B—C11B—C12B—C13B | 171.6 (2) |
C10A—C11A—C12A—C13A | −47.3 (3) | C10B—C11B—C12B—C13B | 49.9 (4) |
C7A—C11A—C12A—C13A | 77.8 (3) | C7B—C11B—C12B—C13B | −74.4 (3) |
C18A—C11A—C12A—C17A | 12.7 (2) | C18B—C11B—C12B—C17B | −10.7 (2) |
C10A—C11A—C12A—C17A | 134.5 (2) | C10B—C11B—C12B—C17B | −132.5 (2) |
C7A—C11A—C12A—C17A | −100.4 (2) | C7B—C11B—C12B—C17B | 103.2 (2) |
C17A—C12A—C13A—C14A | −1.2 (3) | C17B—C12B—C13B—C14B | −0.7 (3) |
C11A—C12A—C13A—C14A | −179.3 (2) | C11B—C12B—C13B—C14B | 176.8 (2) |
C12A—C13A—C14A—C15A | 1.7 (4) | C12B—C13B—C14B—C15B | 0.7 (4) |
C13A—C14A—C15A—C16A | −0.7 (4) | C13B—C14B—C15B—C16B | −0.5 (4) |
C14A—C15A—C16A—C17A | −0.8 (4) | C14B—C15B—C16B—C17B | 0.3 (4) |
C15A—C16A—C17A—C12A | 1.3 (4) | C15B—C16B—C17B—C12B | −0.4 (4) |
C15A—C16A—C17A—N2A | −173.3 (2) | C15B—C16B—C17B—N2B | 177.0 (2) |
C13A—C12A—C17A—C16A | −0.3 (3) | C13B—C12B—C17B—C16B | 0.6 (4) |
C11A—C12A—C17A—C16A | 178.2 (2) | C11B—C12B—C17B—C16B | −177.4 (2) |
C13A—C12A—C17A—N2A | 175.16 (19) | C13B—C12B—C17B—N2B | −177.2 (2) |
C11A—C12A—C17A—N2A | −6.4 (2) | C11B—C12B—C17B—N2B | 4.8 (3) |
C12A—C11A—C18A—O3A | 164.8 (2) | C12B—C11B—C18B—O3B | −166.3 (2) |
C10A—C11A—C18A—O3A | 33.5 (3) | C10B—C11B—C18B—O3B | −34.9 (3) |
C7A—C11A—C18A—O3A | −76.6 (3) | C7B—C11B—C18B—O3B | 75.0 (3) |
C12A—C11A—C18A—N2A | −14.9 (2) | C12B—C11B—C18B—N2B | 13.1 (2) |
C10A—C11A—C18A—N2A | −146.24 (18) | C10B—C11B—C18B—N2B | 144.50 (18) |
C7A—C11A—C18A—N2A | 103.63 (19) | C7B—C11B—C18B—N2B | −105.6 (2) |
C9A—C10A—C19A—C24A | 129.2 (2) | C9B—C10B—C19B—C24B | −128.9 (2) |
C11A—C10A—C19A—C24A | −105.8 (2) | C11B—C10B—C19B—C24B | 105.9 (2) |
C9A—C10A—C19A—C20A | −48.8 (3) | C9B—C10B—C19B—C20B | 45.9 (3) |
C11A—C10A—C19A—C20A | 76.2 (3) | C11B—C10B—C19B—C20B | −79.3 (3) |
C24A—C19A—C20A—C21A | 1.1 (4) | C24B—C19B—C20B—C21B | −0.4 (4) |
C10A—C19A—C20A—C21A | 179.0 (2) | C10B—C19B—C20B—C21B | −175.2 (2) |
C19A—C20A—C21A—C22A | −0.9 (4) | C19B—C20B—C21B—C22B | 1.5 (4) |
C20A—C21A—C22A—C23A | 0.1 (5) | C20B—C21B—C22B—C23B | −1.4 (5) |
C21A—C22A—C23A—C24A | 0.5 (5) | C21B—C22B—C23B—C24B | 0.1 (5) |
C20A—C19A—C24A—C23A | −0.4 (4) | C20B—C19B—C24B—C23B | −0.9 (3) |
C10A—C19A—C24A—C23A | −178.5 (2) | C10B—C19B—C24B—C23B | 174.1 (2) |
C22A—C23A—C24A—C19A | −0.4 (4) | C22B—C23B—C24B—C19B | 1.1 (4) |
O2A—C9A—C25A—C26A | −126.8 (2) | O2B—C9B—C25B—C26B | 116.1 (2) |
C10A—C9A—C25A—C26A | 116.1 (3) | C10B—C9B—C25B—C26B | −127.2 (2) |
O2A—C9A—C25A—C30A | 51.2 (3) | O2B—C9B—C25B—C30B | −61.6 (3) |
C10A—C9A—C25A—C30A | −65.9 (3) | C10B—C9B—C25B—C30B | 55.0 (3) |
C30A—C25A—C26A—C27A | 0.4 (4) | C30B—C25B—C26B—C27B | −0.2 (4) |
C9A—C25A—C26A—C27A | 178.5 (2) | C9B—C25B—C26B—C27B | −178.0 (2) |
C25A—C26A—C27A—C28A | −0.6 (4) | C25B—C26B—C27B—C28B | 0.7 (4) |
C26A—C27A—C28A—C29A | 0.3 (4) | C26B—C27B—C28B—C29B | −1.4 (4) |
C26A—C27A—C28A—Cl1A | −179.4 (2) | C26B—C27B—C28B—Cl1B | 177.89 (19) |
C27A—C28A—C29A—C30A | 0.2 (4) | C27B—C28B—C29B—C30B | 1.4 (4) |
Cl1A—C28A—C29A—C30A | 179.9 (2) | Cl1B—C28B—C29B—C30B | −177.82 (18) |
C28A—C29A—C30A—C25A | −0.4 (4) | C28B—C29B—C30B—C25B | −0.9 (4) |
C26A—C25A—C30A—C29A | 0.1 (4) | C26B—C25B—C30B—C29B | 0.2 (3) |
C9A—C25A—C30A—C29A | −178.0 (2) | C9B—C25B—C30B—C29B | 178.1 (2) |
N1A—C31A—C32A—C33A | −49.5 (4) | N1B—C31B—C32B—C37B | −153.4 (3) |
N1A—C31A—C32A—C37A | 133.2 (2) | N1B—C31B—C32B—C33B | 26.5 (4) |
C37A—C32A—C33A—C34A | 0.4 (4) | C37B—C32B—C33B—C34B | −0.6 (5) |
C31A—C32A—C33A—C34A | −176.9 (3) | C31B—C32B—C33B—C34B | 179.5 (3) |
C32A—C33A—C34A—C35A | −0.2 (5) | C32B—C33B—C34B—C35B | −0.2 (5) |
C33A—C34A—C35A—C36A | −0.2 (5) | C33B—C34B—C35B—C36B | 0.7 (6) |
C34A—C35A—C36A—C37A | 0.3 (5) | C34B—C35B—C36B—C37B | −0.4 (6) |
C35A—C36A—C37A—C32A | −0.1 (4) | C33B—C32B—C37B—C36B | 0.9 (5) |
C33A—C32A—C37A—C36A | −0.3 (4) | C31B—C32B—C37B—C36B | −179.2 (3) |
C31A—C32A—C37A—C36A | 177.1 (2) | C35B—C36B—C37B—C32B | −0.4 (6) |
O1A—C8A—N1A—C1A | −170.9 (2) | O1B—C8B—N1B—C1B | 171.6 (2) |
C7A—C8A—N1A—C1A | 8.5 (2) | C7B—C8B—N1B—C1B | −9.1 (2) |
O1A—C8A—N1A—C31A | −4.2 (4) | O1B—C8B—N1B—C31B | −2.0 (4) |
C7A—C8A—N1A—C31A | 175.14 (19) | C7B—C8B—N1B—C31B | 177.3 (2) |
C2A—C1A—N1A—C8A | 172.7 (2) | C2B—C1B—N1B—C8B | −172.7 (2) |
C6A—C1A—N1A—C8A | −3.7 (2) | C6B—C1B—N1B—C8B | 4.4 (3) |
C2A—C1A—N1A—C31A | 5.9 (3) | C2B—C1B—N1B—C31B | 1.0 (4) |
C6A—C1A—N1A—C31A | −170.5 (2) | C6B—C1B—N1B—C31B | 178.1 (2) |
C32A—C31A—N1A—C8A | 124.1 (2) | C32B—C31B—N1B—C8B | −125.2 (2) |
C32A—C31A—N1A—C1A | −70.9 (3) | C32B—C31B—N1B—C1B | 62.0 (3) |
O3A—C18A—N2A—C38A | 13.6 (4) | O3B—C18B—N2B—C38B | −15.3 (4) |
C11A—C18A—N2A—C38A | −166.6 (2) | C11B—C18B—N2B—C38B | 165.3 (2) |
O3A—C18A—N2A—C17A | −167.7 (2) | O3B—C18B—N2B—C17B | 168.3 (2) |
C11A—C18A—N2A—C17A | 12.0 (2) | C11B—C18B—N2B—C17B | −11.1 (3) |
O4A—C38A—N2A—C18A | 171.2 (2) | O4B—C38B—N2B—C18B | −175.4 (3) |
C39A—C38A—N2A—C18A | −10.0 (4) | C39B—C38B—N2B—C18B | 4.2 (4) |
O4A—C38A—N2A—C17A | −7.3 (4) | O4B—C38B—N2B—C17B | 0.5 (5) |
C39A—C38A—N2A—C17A | 171.6 (2) | C39B—C38B—N2B—C17B | −179.9 (3) |
C16A—C17A—N2A—C18A | 171.4 (2) | C16B—C17B—N2B—C18B | −173.6 (2) |
C12A—C17A—N2A—C18A | −3.7 (3) | C12B—C17B—N2B—C18B | 4.1 (3) |
C16A—C17A—N2A—C38A | −9.9 (4) | C16B—C17B—N2B—C38B | 9.9 (4) |
C12A—C17A—N2A—C38A | 175.0 (2) | C12B—C17B—N2B—C38B | −172.4 (2) |
C6A—C7A—O2A—C9A | 163.65 (17) | C6B—C7B—O2B—C9B | −166.23 (18) |
C8A—C7A—O2A—C9A | −83.6 (2) | C8B—C7B—O2B—C9B | 80.9 (2) |
C11A—C7A—O2A—C9A | 36.2 (2) | C11B—C7B—O2B—C9B | −38.1 (2) |
C25A—C9A—O2A—C7A | −155.90 (17) | C25B—C9B—O2B—C7B | 162.90 (17) |
C10A—C9A—O2A—C7A | −32.6 (2) | C10B—C9B—O2B—C7B | 39.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5A—H5A···O3A | 0.93 | 2.57 | 3.157 (3) | 122 |
C5B—H5B···O3B | 0.93 | 2.56 | 3.118 (4) | 119 |
C9A—H9A···O1A | 0.98 | 2.69 | 3.152 (3) | 109 |
C9B—H9B···O1B | 0.98 | 2.53 | 3.088 (3) | 116 |
C10A—H10A···O3A | 0.98 | 2.39 | 2.881 (3) | 111 |
C10B—H10B···O3B | 0.98 | 2.34 | 2.871 (3) | 113 |
C13A—H13A···O1A | 0.93 | 2.64 | 3.157 (3) | 115 |
C13B—H13B···O1B | 0.93 | 2.49 | 3.003 (3) | 115 |
C16A—H16A···O4A | 0.93 | 2.30 | 2.840 (4) | 117 |
C16B—H16B···O4B | 0.93 | 2.29 | 2.835 (5) | 117 |
C20A—H20A···O1A | 0.93 | 2.43 | 3.256 (3) | 148 |
C20B—H20B···O1B | 0.93 | 2.70 | 3.515 (3) | 147 |
C27B—H27B···O1Ai | 0.93 | 2.59 | 3.374 (3) | 142 |
C30A—H30A···O3A | 0.93 | 2.47 | 3.314 (3) | 151 |
C30B—H30B···O3B | 0.93 | 2.85 | 3.701 (3) | 153 |
C31A—H31A···O1A | 0.97 | 2.53 | 2.913 (3) | 104 |
C31B—H31D···O1B | 0.97 | 2.55 | 2.921 (3) | 104 |
C15A—H15A···Cg3(C19B–C24B) | 0.93 | 2.91 | 3.808 (14) | 163 |
C33A—H33A···Cg4(C12A–C17A) | 0.93 | 2.89 | 3.717 (3) | 149 |
C33B—H33B···Cg5(C12B–C17B) | 0.93 | 2.64 | 3.485 (3) | 151 |
Symmetry code: (i) x−1, y+1, z. |
C39H30N2O4 | F(000) = 1240 |
Mr = 590.65 | Dx = 1.286 Mg m−3 |
Triclinic, P1 | Melting point: 456 K |
a = 9.7565 (10) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 16.6868 (16) Å | Cell parameters from 5092 reflections |
c = 19.9593 (19) Å | θ = 2.4–21.3° |
α = 71.653 (2)° | µ = 0.08 mm−1 |
β = 81.657 (2)° | T = 294 K |
γ = 89.314 (2)° | Needle, colorless |
V = 3049.7 (5) Å3 | 0.11 × 0.08 × 0.06 mm |
Z = 4 |
Bruker SMART APEX CCD area-detector diffractometer | 6882 reflections with I > 2σ(I) |
ω scans | Rint = 0.036 |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | θmax = 25.0°, θmin = 1.4° |
Tmin = 0.96, Tmax = 0.99 | h = −11→11 |
29800 measured reflections | k = −19→19 |
10763 independent reflections | l = −23→23 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.070 | H-atom parameters constrained |
wR(F2) = 0.149 | w = 1/[σ2(Fo2) + (0.0505P)2 + 0.8037P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
10763 reflections | Δρmax = 0.22 e Å−3 |
813 parameters | Δρmin = −0.17 e Å−3 |
C39H30N2O4 | γ = 89.314 (2)° |
Mr = 590.65 | V = 3049.7 (5) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.7565 (10) Å | Mo Kα radiation |
b = 16.6868 (16) Å | µ = 0.08 mm−1 |
c = 19.9593 (19) Å | T = 294 K |
α = 71.653 (2)° | 0.11 × 0.08 × 0.06 mm |
β = 81.657 (2)° |
Bruker SMART APEX CCD area-detector diffractometer | 10763 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 6882 reflections with I > 2σ(I) |
Tmin = 0.96, Tmax = 0.99 | Rint = 0.036 |
29800 measured reflections |
R[F2 > 2σ(F2)] = 0.070 | 0 restraints |
wR(F2) = 0.149 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.22 e Å−3 |
10763 reflections | Δρmin = −0.17 e Å−3 |
813 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
C1A | 0.9292 (3) | 0.66340 (16) | 0.69310 (14) | 0.0573 (7) | |
C2A | 1.0358 (4) | 0.66726 (19) | 0.63901 (16) | 0.0743 (9) | |
H2A | 1.0192 | 0.6610 | 0.5962 | 0.089* | |
C3A | 1.1680 (4) | 0.6808 (2) | 0.65046 (19) | 0.0818 (11) | |
H3A | 1.2419 | 0.6840 | 0.6145 | 0.098* | |
C4A | 1.1935 (3) | 0.6896 (2) | 0.71335 (19) | 0.0767 (10) | |
H4A | 1.2841 | 0.6977 | 0.7199 | 0.092* | |
C5A | 1.0845 (3) | 0.68656 (18) | 0.76760 (16) | 0.0655 (8) | |
H5A | 1.1014 | 0.6920 | 0.8107 | 0.079* | |
C6A | 0.9517 (3) | 0.67536 (16) | 0.75628 (14) | 0.0509 (7) | |
C7A | 0.8153 (3) | 0.66699 (16) | 0.80431 (13) | 0.0485 (7) | |
C8A | 0.7161 (3) | 0.63756 (17) | 0.76209 (14) | 0.0542 (7) | |
C9A | 0.7062 (3) | 0.61634 (16) | 0.92145 (13) | 0.0479 (6) | |
H9A | 0.6242 | 0.5864 | 0.9166 | 0.057* | |
C10A | 0.6811 (2) | 0.71203 (15) | 0.90047 (13) | 0.0448 (6) | |
H10A | 0.7333 | 0.7339 | 0.9298 | 0.054* | |
C11A | 0.7580 (2) | 0.74921 (15) | 0.82183 (13) | 0.0454 (6) | |
C12A | 0.6900 (3) | 0.80860 (16) | 0.76294 (13) | 0.0505 (7) | |
C13A | 0.5626 (3) | 0.80414 (19) | 0.74198 (15) | 0.0619 (8) | |
H13A | 0.5011 | 0.7589 | 0.7668 | 0.074* | |
C14A | 0.5265 (4) | 0.8669 (2) | 0.68415 (17) | 0.0789 (10) | |
H14A | 0.4399 | 0.8641 | 0.6705 | 0.095* | |
C15A | 0.6162 (5) | 0.9325 (2) | 0.64708 (18) | 0.0874 (11) | |
H15A | 0.5906 | 0.9737 | 0.6078 | 0.105* | |
C16A | 0.7447 (4) | 0.9396 (2) | 0.66623 (17) | 0.0800 (10) | |
H16A | 0.8059 | 0.9847 | 0.6406 | 0.096* | |
C17A | 0.7796 (3) | 0.87694 (17) | 0.72516 (15) | 0.0602 (8) | |
C18A | 0.8842 (3) | 0.80232 (17) | 0.82162 (16) | 0.0546 (7) | |
C19A | 0.5318 (3) | 0.73458 (16) | 0.91701 (13) | 0.0471 (6) | |
C20A | 0.4203 (3) | 0.6902 (2) | 0.90795 (15) | 0.0654 (8) | |
H20A | 0.4367 | 0.6463 | 0.8888 | 0.078* | |
C21A | 0.2860 (3) | 0.7099 (3) | 0.92674 (18) | 0.0841 (10) | |
H21A | 0.2129 | 0.6792 | 0.9203 | 0.101* | |
C22A | 0.2593 (4) | 0.7738 (3) | 0.9546 (2) | 0.0932 (12) | |
H22A | 0.1683 | 0.7872 | 0.9670 | 0.112* | |
C23A | 0.3672 (4) | 0.8184 (2) | 0.96447 (19) | 0.0870 (11) | |
H23A | 0.3493 | 0.8623 | 0.9835 | 0.104* | |
C24A | 0.5030 (3) | 0.79864 (18) | 0.94625 (15) | 0.0622 (8) | |
H24A | 0.5755 | 0.8289 | 0.9538 | 0.075* | |
C25A | 0.7417 (3) | 0.57877 (16) | 0.99551 (13) | 0.0496 (7) | |
C26A | 0.6404 (3) | 0.54221 (18) | 1.05194 (15) | 0.0655 (8) | |
H26A | 0.5492 | 0.5393 | 1.0441 | 0.079* | |
C27A | 0.6726 (5) | 0.5095 (2) | 1.12059 (17) | 0.0824 (11) | |
H27A | 0.6026 | 0.4857 | 1.1586 | 0.099* | |
C28A | 0.8047 (5) | 0.5119 (2) | 1.13261 (19) | 0.0899 (11) | |
H28A | 0.8260 | 0.4897 | 1.1787 | 0.108* | |
C29A | 0.9057 (4) | 0.5469 (3) | 1.0774 (2) | 0.1079 (14) | |
H29A | 0.9970 | 0.5481 | 1.0854 | 0.130* | |
C30A | 0.8743 (3) | 0.5807 (2) | 1.00904 (17) | 0.0891 (11) | |
H30A | 0.9449 | 0.6052 | 0.9716 | 0.107* | |
C31A | 0.7281 (4) | 0.6229 (2) | 0.64126 (16) | 0.0827 (10) | |
H31A | 0.6300 | 0.6093 | 0.6573 | 0.099* | |
H31B | 0.7716 | 0.5729 | 0.6345 | 0.099* | |
C32A | 0.7457 (3) | 0.6925 (2) | 0.57063 (15) | 0.0659 (8) | |
C33A | 0.7514 (3) | 0.7765 (2) | 0.56645 (17) | 0.0729 (9) | |
H33A | 0.7454 | 0.7912 | 0.6080 | 0.087* | |
C34A | 0.7660 (3) | 0.8388 (2) | 0.50110 (19) | 0.0811 (10) | |
H34A | 0.7698 | 0.8952 | 0.4990 | 0.097* | |
C35A | 0.7748 (3) | 0.8187 (3) | 0.43915 (19) | 0.0877 (11) | |
H35A | 0.7847 | 0.8611 | 0.3952 | 0.105* | |
C36A | 0.7687 (3) | 0.7357 (3) | 0.44279 (18) | 0.0852 (11) | |
H36A | 0.7741 | 0.7215 | 0.4010 | 0.102* | |
C37A | 0.7548 (3) | 0.6729 (2) | 0.50763 (18) | 0.0752 (9) | |
H37A | 0.7514 | 0.6166 | 0.5093 | 0.090* | |
C38A | 1.0177 (4) | 0.9267 (3) | 0.7323 (3) | 0.1062 (14) | |
C39A | 1.1367 (4) | 0.9099 (3) | 0.7717 (3) | 0.153 (2) | |
H39A | 1.1168 | 0.9272 | 0.8135 | 0.230* | |
H39B | 1.2172 | 0.9409 | 0.7417 | 0.230* | |
H39C | 1.1539 | 0.8505 | 0.7855 | 0.230* | |
N1A | 0.7870 (3) | 0.64435 (14) | 0.69650 (12) | 0.0621 (6) | |
N2A | 0.9007 (3) | 0.87137 (14) | 0.75878 (13) | 0.0664 (7) | |
O1A | 0.5965 (2) | 0.61316 (13) | 0.78326 (10) | 0.0718 (6) | |
O2A | 0.82178 (18) | 0.60682 (10) | 0.87153 (9) | 0.0533 (5) | |
O3A | 0.9568 (2) | 0.78663 (13) | 0.86773 (12) | 0.0708 (6) | |
O4A | 1.0189 (4) | 0.9846 (2) | 0.6787 (2) | 0.1670 (15) | |
C1B | 0.3966 (3) | 0.66787 (18) | 0.19443 (15) | 0.0611 (8) | |
C2B | 0.3740 (4) | 0.6507 (2) | 0.13385 (17) | 0.0855 (11) | |
H2B | 0.4401 | 0.6656 | 0.0930 | 0.103* | |
C3B | 0.2513 (4) | 0.6109 (3) | 0.13551 (19) | 0.1064 (14) | |
H3B | 0.2341 | 0.5982 | 0.0953 | 0.128* | |
C4B | 0.1526 (4) | 0.5894 (3) | 0.1956 (2) | 0.1095 (14) | |
H4B | 0.0709 | 0.5610 | 0.1960 | 0.131* | |
C5B | 0.1743 (3) | 0.6098 (2) | 0.25536 (17) | 0.0845 (11) | |
H5B | 0.1070 | 0.5962 | 0.2957 | 0.101* | |
C6B | 0.2955 (3) | 0.65014 (18) | 0.25435 (14) | 0.0587 (8) | |
C7B | 0.3512 (3) | 0.67667 (17) | 0.31074 (13) | 0.0525 (7) | |
C8B | 0.5065 (3) | 0.69567 (17) | 0.27855 (16) | 0.0558 (7) | |
C9B | 0.3493 (3) | 0.64670 (16) | 0.43178 (13) | 0.0517 (7) | |
H9B | 0.4456 | 0.6654 | 0.4285 | 0.062* | |
C10B | 0.2580 (3) | 0.72289 (16) | 0.41355 (13) | 0.0485 (7) | |
H10B | 0.1624 | 0.6999 | 0.4267 | 0.058* | |
C11B | 0.2836 (3) | 0.75674 (16) | 0.32999 (13) | 0.0471 (6) | |
C12B | 0.3621 (3) | 0.83932 (16) | 0.29240 (13) | 0.0487 (7) | |
C13B | 0.4889 (3) | 0.86791 (18) | 0.30007 (15) | 0.0598 (8) | |
H13B | 0.5388 | 0.8346 | 0.3343 | 0.072* | |
C14B | 0.5409 (4) | 0.9463 (2) | 0.25652 (19) | 0.0748 (9) | |
H14B | 0.6266 | 0.9660 | 0.2613 | 0.090* | |
C15B | 0.4675 (4) | 0.9952 (2) | 0.20653 (19) | 0.0818 (11) | |
H15B | 0.5052 | 1.0475 | 0.1771 | 0.098* | |
C16B | 0.3397 (4) | 0.9695 (2) | 0.19824 (16) | 0.0746 (9) | |
H16B | 0.2898 | 1.0038 | 0.1644 | 0.090* | |
C17B | 0.2877 (3) | 0.89059 (18) | 0.24230 (14) | 0.0564 (7) | |
C18B | 0.1444 (3) | 0.77372 (19) | 0.30262 (15) | 0.0582 (7) | |
C19B | 0.2660 (3) | 0.78642 (16) | 0.45256 (12) | 0.0476 (7) | |
C20B | 0.3841 (3) | 0.80219 (18) | 0.47761 (14) | 0.0576 (7) | |
H20B | 0.4648 | 0.7748 | 0.4684 | 0.069* | |
C21B | 0.3842 (4) | 0.8580 (2) | 0.51612 (16) | 0.0697 (9) | |
H21B | 0.4649 | 0.8680 | 0.5324 | 0.084* | |
C22B | 0.2665 (4) | 0.8985 (2) | 0.53035 (17) | 0.0766 (9) | |
H22B | 0.2666 | 0.9357 | 0.5566 | 0.092* | |
C23B | 0.1492 (4) | 0.8841 (2) | 0.50592 (18) | 0.0769 (9) | |
H23B | 0.0690 | 0.9119 | 0.5152 | 0.092* | |
C24B | 0.1486 (3) | 0.82850 (19) | 0.46735 (15) | 0.0637 (8) | |
H24B | 0.0676 | 0.8192 | 0.4510 | 0.076* | |
C25B | 0.3041 (3) | 0.58141 (17) | 0.50313 (14) | 0.0550 (7) | |
C26B | 0.3909 (3) | 0.5596 (2) | 0.55366 (17) | 0.0732 (9) | |
H26B | 0.4791 | 0.5849 | 0.5436 | 0.088* | |
C27B | 0.3486 (4) | 0.5001 (2) | 0.61952 (19) | 0.0912 (11) | |
H27B | 0.4080 | 0.4864 | 0.6536 | 0.109* | |
C28B | 0.2208 (5) | 0.4616 (2) | 0.63468 (19) | 0.0912 (11) | |
H28B | 0.1930 | 0.4212 | 0.6788 | 0.109* | |
C29B | 0.1340 (4) | 0.4823 (2) | 0.58510 (19) | 0.0875 (11) | |
H29B | 0.0466 | 0.4559 | 0.5952 | 0.105* | |
C30B | 0.1749 (3) | 0.54203 (19) | 0.51983 (15) | 0.0712 (9) | |
H30B | 0.1141 | 0.5561 | 0.4864 | 0.085* | |
C31B | 0.6528 (3) | 0.70634 (19) | 0.16345 (17) | 0.0747 (9) | |
H31C | 0.6576 | 0.6628 | 0.1405 | 0.090* | |
H31D | 0.7249 | 0.6963 | 0.1936 | 0.090* | |
C32B | 0.6829 (3) | 0.79056 (19) | 0.10680 (14) | 0.0586 (8) | |
C33B | 0.6056 (4) | 0.8591 (2) | 0.10648 (16) | 0.0795 (10) | |
H33B | 0.5279 | 0.8535 | 0.1409 | 0.095* | |
C34B | 0.6406 (5) | 0.9364 (2) | 0.05598 (19) | 0.1055 (14) | |
H34B | 0.5865 | 0.9825 | 0.0567 | 0.127* | |
C35B | 0.7536 (5) | 0.9463 (3) | 0.0051 (2) | 0.1127 (15) | |
H35B | 0.7775 | 0.9989 | −0.0286 | 0.135* | |
C36B | 0.8309 (4) | 0.8786 (3) | 0.00398 (19) | 0.1021 (13) | |
H36B | 0.9077 | 0.8847 | −0.0310 | 0.123* | |
C37B | 0.7965 (3) | 0.8007 (2) | 0.05428 (17) | 0.0797 (10) | |
H37B | 0.8502 | 0.7547 | 0.0529 | 0.096* | |
C38B | 0.0523 (4) | 0.8859 (3) | 0.2049 (2) | 0.0951 (12) | |
C39B | −0.0759 (4) | 0.8353 (3) | 0.2140 (2) | 0.1394 (19) | |
H39D | −0.1259 | 0.8265 | 0.2610 | 0.209* | |
H39E | −0.0528 | 0.7817 | 0.2079 | 0.209* | |
H39F | −0.1325 | 0.8648 | 0.1791 | 0.209* | |
N1B | 0.5191 (2) | 0.69772 (14) | 0.20844 (12) | 0.0609 (6) | |
N2B | 0.1565 (2) | 0.85061 (16) | 0.24650 (12) | 0.0625 (6) | |
O1B | 0.6002 (2) | 0.70484 (13) | 0.30892 (11) | 0.0701 (6) | |
O2B | 0.33736 (19) | 0.61006 (11) | 0.37630 (9) | 0.0595 (5) | |
O3B | 0.0413 (2) | 0.72933 (15) | 0.32619 (11) | 0.0780 (6) | |
O4B | 0.0744 (3) | 0.9560 (2) | 0.16236 (17) | 0.1432 (13) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1A | 0.075 (2) | 0.0444 (16) | 0.0443 (17) | 0.0066 (14) | 0.0055 (15) | −0.0084 (13) |
C2A | 0.092 (3) | 0.069 (2) | 0.0536 (19) | 0.0109 (19) | 0.0090 (18) | −0.0172 (16) |
C3A | 0.086 (3) | 0.076 (2) | 0.059 (2) | 0.0177 (19) | 0.0250 (19) | −0.0039 (18) |
C4A | 0.062 (2) | 0.077 (2) | 0.072 (2) | 0.0071 (17) | 0.0107 (18) | −0.0061 (18) |
C5A | 0.064 (2) | 0.065 (2) | 0.0571 (19) | 0.0076 (16) | −0.0002 (16) | −0.0088 (15) |
C6A | 0.0553 (18) | 0.0451 (16) | 0.0443 (16) | 0.0033 (13) | 0.0038 (13) | −0.0079 (13) |
C7A | 0.0552 (16) | 0.0458 (16) | 0.0383 (15) | −0.0008 (13) | −0.0007 (12) | −0.0072 (12) |
C8A | 0.0650 (19) | 0.0464 (17) | 0.0478 (17) | −0.0049 (14) | −0.0014 (15) | −0.0132 (13) |
C9A | 0.0474 (15) | 0.0495 (16) | 0.0430 (15) | −0.0061 (12) | 0.0015 (12) | −0.0125 (13) |
C10A | 0.0448 (15) | 0.0489 (16) | 0.0395 (14) | −0.0064 (12) | −0.0035 (11) | −0.0133 (12) |
C11A | 0.0459 (15) | 0.0453 (15) | 0.0421 (15) | −0.0034 (12) | 0.0007 (12) | −0.0127 (12) |
C12A | 0.0595 (18) | 0.0485 (16) | 0.0390 (15) | 0.0042 (14) | 0.0026 (13) | −0.0121 (13) |
C13A | 0.068 (2) | 0.071 (2) | 0.0462 (17) | 0.0087 (16) | −0.0085 (15) | −0.0178 (16) |
C14A | 0.094 (3) | 0.091 (3) | 0.051 (2) | 0.031 (2) | −0.0164 (19) | −0.0208 (19) |
C15A | 0.126 (3) | 0.078 (3) | 0.053 (2) | 0.040 (3) | −0.013 (2) | −0.0144 (19) |
C16A | 0.121 (3) | 0.051 (2) | 0.051 (2) | 0.006 (2) | 0.016 (2) | −0.0048 (16) |
C17A | 0.076 (2) | 0.0481 (18) | 0.0493 (17) | 0.0037 (15) | 0.0090 (16) | −0.0138 (15) |
C18A | 0.0502 (17) | 0.0527 (18) | 0.0604 (19) | −0.0051 (14) | 0.0034 (15) | −0.0220 (16) |
C19A | 0.0501 (16) | 0.0518 (16) | 0.0350 (14) | −0.0022 (13) | −0.0026 (12) | −0.0090 (13) |
C20A | 0.0540 (19) | 0.082 (2) | 0.0605 (19) | −0.0038 (16) | −0.0058 (15) | −0.0250 (17) |
C21A | 0.050 (2) | 0.121 (3) | 0.077 (2) | −0.005 (2) | −0.0080 (17) | −0.025 (2) |
C22A | 0.058 (2) | 0.116 (3) | 0.092 (3) | 0.021 (2) | 0.004 (2) | −0.021 (2) |
C23A | 0.089 (3) | 0.077 (2) | 0.088 (3) | 0.021 (2) | 0.009 (2) | −0.027 (2) |
C24A | 0.065 (2) | 0.0602 (19) | 0.0569 (18) | 0.0019 (15) | 0.0019 (15) | −0.0178 (15) |
C25A | 0.0560 (17) | 0.0437 (15) | 0.0442 (16) | −0.0009 (13) | 0.0009 (13) | −0.0107 (13) |
C26A | 0.084 (2) | 0.0594 (19) | 0.0487 (18) | −0.0217 (16) | 0.0037 (16) | −0.0167 (15) |
C27A | 0.134 (3) | 0.058 (2) | 0.045 (2) | −0.032 (2) | 0.015 (2) | −0.0134 (16) |
C28A | 0.139 (4) | 0.068 (2) | 0.057 (2) | 0.019 (2) | −0.024 (3) | −0.0087 (18) |
C29A | 0.089 (3) | 0.161 (4) | 0.067 (3) | 0.033 (3) | −0.029 (2) | −0.021 (3) |
C30A | 0.064 (2) | 0.133 (3) | 0.055 (2) | 0.007 (2) | −0.0074 (17) | −0.009 (2) |
C31A | 0.120 (3) | 0.073 (2) | 0.064 (2) | −0.013 (2) | −0.0082 (19) | −0.0354 (19) |
C32A | 0.071 (2) | 0.080 (2) | 0.0531 (19) | −0.0031 (17) | −0.0042 (15) | −0.0322 (17) |
C33A | 0.084 (2) | 0.083 (2) | 0.057 (2) | 0.0093 (19) | −0.0078 (17) | −0.0304 (19) |
C34A | 0.078 (2) | 0.088 (3) | 0.072 (2) | 0.0153 (19) | −0.0113 (19) | −0.019 (2) |
C35A | 0.068 (2) | 0.126 (4) | 0.060 (2) | 0.009 (2) | −0.0130 (17) | −0.014 (2) |
C36A | 0.066 (2) | 0.144 (4) | 0.052 (2) | 0.001 (2) | −0.0084 (16) | −0.039 (2) |
C37A | 0.069 (2) | 0.103 (3) | 0.067 (2) | −0.0035 (18) | −0.0069 (17) | −0.046 (2) |
C38A | 0.094 (3) | 0.073 (3) | 0.127 (4) | −0.038 (2) | 0.024 (3) | −0.013 (3) |
C39A | 0.073 (3) | 0.123 (4) | 0.234 (6) | −0.056 (3) | −0.002 (3) | −0.020 (4) |
N1A | 0.0794 (18) | 0.0598 (16) | 0.0482 (14) | −0.0066 (13) | 0.0000 (13) | −0.0228 (12) |
N2A | 0.0694 (17) | 0.0474 (15) | 0.0700 (17) | −0.0157 (12) | 0.0150 (14) | −0.0119 (13) |
O1A | 0.0723 (14) | 0.0779 (15) | 0.0660 (13) | −0.0204 (12) | −0.0014 (11) | −0.0272 (11) |
O2A | 0.0609 (11) | 0.0477 (11) | 0.0436 (10) | 0.0033 (9) | 0.0017 (9) | −0.0079 (9) |
O3A | 0.0532 (12) | 0.0824 (15) | 0.0804 (15) | −0.0144 (11) | −0.0094 (11) | −0.0303 (12) |
O4A | 0.157 (3) | 0.120 (3) | 0.158 (3) | −0.072 (2) | 0.015 (2) | 0.035 (2) |
C1B | 0.074 (2) | 0.0552 (18) | 0.0505 (18) | −0.0120 (15) | 0.0078 (15) | −0.0183 (14) |
C2B | 0.105 (3) | 0.094 (3) | 0.055 (2) | −0.024 (2) | 0.0153 (19) | −0.0313 (19) |
C3B | 0.127 (3) | 0.139 (4) | 0.063 (2) | −0.041 (3) | 0.001 (2) | −0.052 (2) |
C4B | 0.114 (3) | 0.146 (4) | 0.077 (3) | −0.060 (3) | 0.001 (2) | −0.052 (3) |
C5B | 0.087 (2) | 0.107 (3) | 0.059 (2) | −0.044 (2) | 0.0105 (17) | −0.0322 (19) |
C6B | 0.0668 (19) | 0.0604 (18) | 0.0451 (16) | −0.0179 (15) | 0.0060 (14) | −0.0170 (14) |
C7B | 0.0590 (17) | 0.0506 (16) | 0.0416 (15) | −0.0122 (13) | 0.0053 (13) | −0.0109 (13) |
C8B | 0.0609 (19) | 0.0415 (16) | 0.060 (2) | −0.0051 (14) | 0.0005 (16) | −0.0122 (14) |
C9B | 0.0593 (17) | 0.0487 (16) | 0.0445 (16) | −0.0060 (13) | −0.0009 (13) | −0.0135 (13) |
C10B | 0.0471 (15) | 0.0536 (17) | 0.0386 (14) | −0.0078 (13) | 0.0003 (12) | −0.0085 (13) |
C11B | 0.0453 (15) | 0.0530 (16) | 0.0394 (14) | −0.0086 (12) | −0.0007 (12) | −0.0115 (12) |
C12B | 0.0540 (17) | 0.0509 (16) | 0.0377 (15) | −0.0038 (13) | 0.0046 (13) | −0.0139 (13) |
C13B | 0.0600 (19) | 0.0610 (19) | 0.0575 (18) | −0.0105 (15) | 0.0063 (14) | −0.0235 (15) |
C14B | 0.080 (2) | 0.063 (2) | 0.079 (2) | −0.0249 (18) | 0.0153 (19) | −0.0297 (19) |
C15B | 0.111 (3) | 0.050 (2) | 0.072 (2) | −0.017 (2) | 0.026 (2) | −0.0175 (18) |
C16B | 0.101 (3) | 0.062 (2) | 0.0511 (19) | 0.0087 (19) | 0.0057 (18) | −0.0121 (16) |
C17B | 0.0667 (19) | 0.0594 (19) | 0.0396 (16) | 0.0005 (15) | 0.0045 (14) | −0.0163 (14) |
C18B | 0.0563 (19) | 0.073 (2) | 0.0447 (17) | −0.0074 (16) | 0.0002 (14) | −0.0202 (15) |
C19B | 0.0513 (17) | 0.0504 (16) | 0.0333 (14) | −0.0008 (13) | 0.0003 (12) | −0.0051 (12) |
C20B | 0.0581 (18) | 0.0666 (19) | 0.0519 (17) | 0.0027 (15) | −0.0077 (14) | −0.0242 (15) |
C21B | 0.079 (2) | 0.075 (2) | 0.060 (2) | 0.0017 (18) | −0.0178 (17) | −0.0246 (17) |
C22B | 0.110 (3) | 0.062 (2) | 0.061 (2) | 0.005 (2) | −0.012 (2) | −0.0249 (17) |
C23B | 0.083 (2) | 0.069 (2) | 0.077 (2) | 0.0231 (18) | −0.0006 (19) | −0.0263 (19) |
C24B | 0.0599 (19) | 0.069 (2) | 0.0582 (18) | 0.0064 (16) | −0.0058 (15) | −0.0157 (16) |
C25B | 0.0678 (19) | 0.0471 (17) | 0.0463 (16) | 0.0002 (14) | −0.0012 (15) | −0.0125 (13) |
C26B | 0.070 (2) | 0.068 (2) | 0.069 (2) | 0.0083 (17) | −0.0100 (18) | −0.0045 (18) |
C27B | 0.097 (3) | 0.086 (3) | 0.067 (2) | 0.018 (2) | −0.017 (2) | 0.009 (2) |
C28B | 0.116 (3) | 0.069 (2) | 0.060 (2) | 0.010 (2) | 0.010 (2) | 0.0097 (18) |
C29B | 0.100 (3) | 0.076 (2) | 0.064 (2) | −0.021 (2) | 0.013 (2) | −0.0013 (19) |
C30B | 0.084 (2) | 0.072 (2) | 0.0478 (18) | −0.0184 (18) | −0.0018 (16) | −0.0068 (16) |
C31B | 0.071 (2) | 0.064 (2) | 0.082 (2) | −0.0030 (16) | 0.0209 (17) | −0.0281 (18) |
C32B | 0.0624 (18) | 0.066 (2) | 0.0497 (17) | −0.0102 (16) | 0.0081 (14) | −0.0276 (15) |
C33B | 0.104 (3) | 0.066 (2) | 0.058 (2) | −0.008 (2) | 0.0207 (18) | −0.0188 (18) |
C34B | 0.161 (4) | 0.070 (3) | 0.069 (2) | −0.005 (2) | 0.021 (3) | −0.014 (2) |
C35B | 0.162 (4) | 0.091 (3) | 0.065 (3) | −0.032 (3) | 0.021 (3) | −0.012 (2) |
C36B | 0.102 (3) | 0.129 (4) | 0.062 (2) | −0.043 (3) | 0.030 (2) | −0.028 (3) |
C37B | 0.069 (2) | 0.104 (3) | 0.065 (2) | −0.0132 (19) | 0.0149 (17) | −0.037 (2) |
C38B | 0.092 (3) | 0.131 (4) | 0.053 (2) | 0.018 (3) | −0.019 (2) | −0.014 (2) |
C39B | 0.094 (3) | 0.191 (5) | 0.132 (4) | −0.004 (3) | −0.070 (3) | −0.026 (4) |
N1B | 0.0604 (15) | 0.0591 (15) | 0.0578 (16) | −0.0096 (12) | 0.0139 (12) | −0.0206 (12) |
N2B | 0.0638 (16) | 0.0783 (18) | 0.0427 (14) | 0.0073 (14) | −0.0105 (12) | −0.0144 (13) |
O1B | 0.0590 (13) | 0.0707 (14) | 0.0786 (15) | −0.0013 (11) | −0.0114 (11) | −0.0201 (12) |
O2B | 0.0795 (13) | 0.0503 (11) | 0.0437 (11) | −0.0117 (10) | 0.0029 (9) | −0.0125 (9) |
O3B | 0.0524 (13) | 0.1065 (18) | 0.0683 (14) | −0.0194 (12) | −0.0023 (11) | −0.0203 (13) |
O4B | 0.125 (2) | 0.165 (3) | 0.099 (2) | 0.021 (2) | −0.0390 (19) | 0.025 (2) |
C1A—C2A | 1.372 (4) | C1B—C2B | 1.375 (4) |
C1A—C6A | 1.385 (4) | C1B—C6B | 1.390 (4) |
C1A—N1A | 1.414 (4) | C1B—N1B | 1.398 (4) |
C2A—C3A | 1.376 (5) | C2B—C3B | 1.367 (5) |
C2A—H2A | 0.9300 | C2B—H2B | 0.9300 |
C3A—C4A | 1.367 (5) | C3B—C4B | 1.377 (5) |
C3A—H3A | 0.9300 | C3B—H3B | 0.9300 |
C4A—C5A | 1.392 (4) | C4B—C5B | 1.384 (4) |
C4A—H4A | 0.9300 | C4B—H4B | 0.9300 |
C5A—C6A | 1.372 (4) | C5B—C6B | 1.362 (4) |
C5A—H5A | 0.9300 | C5B—H5B | 0.9300 |
C6A—C7A | 1.504 (3) | C6B—C7B | 1.501 (4) |
C7A—O2A | 1.410 (3) | C7B—O2B | 1.415 (3) |
C7A—C8A | 1.548 (4) | C7B—C8B | 1.552 (4) |
C7A—C11A | 1.595 (3) | C7B—C11B | 1.611 (4) |
C8A—O1A | 1.211 (3) | C8B—O1B | 1.204 (3) |
C8A—N1A | 1.360 (3) | C8B—N1B | 1.376 (4) |
C9A—O2A | 1.435 (3) | C9B—O2B | 1.442 (3) |
C9A—C25A | 1.503 (4) | C9B—C25B | 1.504 (4) |
C9A—C10A | 1.544 (3) | C9B—C10B | 1.523 (4) |
C9A—H9A | 0.9800 | C9B—H9B | 0.9800 |
C10A—C19A | 1.516 (3) | C10B—C19B | 1.508 (4) |
C10A—C11A | 1.571 (3) | C10B—C11B | 1.566 (3) |
C10A—H10A | 0.9800 | C10B—H10B | 0.9800 |
C11A—C12A | 1.510 (4) | C11B—C12B | 1.502 (3) |
C11A—C18A | 1.525 (4) | C11B—C18B | 1.528 (4) |
C12A—C13A | 1.377 (4) | C12B—C13B | 1.377 (4) |
C12A—C17A | 1.388 (4) | C12B—C17B | 1.384 (4) |
C13A—C14A | 1.379 (4) | C13B—C14B | 1.377 (4) |
C13A—H13A | 0.9300 | C13B—H13B | 0.9300 |
C14A—C15A | 1.356 (5) | C14B—C15B | 1.362 (5) |
C14A—H14A | 0.9300 | C14B—H14B | 0.9300 |
C15A—C16A | 1.380 (5) | C15B—C16B | 1.372 (5) |
C15A—H15A | 0.9300 | C15B—H15B | 0.9300 |
C16A—C17A | 1.387 (4) | C16B—C17B | 1.387 (4) |
C16A—H16A | 0.9300 | C16B—H16B | 0.9300 |
C17A—N2A | 1.429 (4) | C17B—N2B | 1.430 (3) |
C18A—O3A | 1.204 (3) | C18B—O3B | 1.201 (3) |
C18A—N2A | 1.401 (4) | C18B—N2B | 1.405 (4) |
C19A—C24A | 1.378 (4) | C19B—C20B | 1.379 (4) |
C19A—C20A | 1.388 (4) | C19B—C24B | 1.381 (4) |
C20A—C21A | 1.374 (4) | C20B—C21B | 1.382 (4) |
C20A—H20A | 0.9300 | C20B—H20B | 0.9300 |
C21A—C22A | 1.356 (5) | C21B—C22B | 1.365 (4) |
C21A—H21A | 0.9300 | C21B—H21B | 0.9300 |
C22A—C23A | 1.368 (5) | C22B—C23B | 1.359 (4) |
C22A—H22A | 0.9300 | C22B—H22B | 0.9300 |
C23A—C24A | 1.387 (4) | C23B—C24B | 1.380 (4) |
C23A—H23A | 0.9300 | C23B—H23B | 0.9300 |
C24A—H24A | 0.9300 | C24B—H24B | 0.9300 |
C25A—C30A | 1.362 (4) | C25B—C26B | 1.370 (4) |
C25A—C26A | 1.370 (4) | C25B—C30B | 1.376 (4) |
C26A—C27A | 1.387 (4) | C26B—C27B | 1.384 (4) |
C26A—H26A | 0.9300 | C26B—H26B | 0.9300 |
C27A—C28A | 1.348 (5) | C27B—C28B | 1.359 (5) |
C27A—H27A | 0.9300 | C27B—H27B | 0.9300 |
C28A—C29A | 1.349 (5) | C28B—C29B | 1.355 (5) |
C28A—H28A | 0.9300 | C28B—H28B | 0.9300 |
C29A—C30A | 1.380 (4) | C29B—C30B | 1.375 (4) |
C29A—H29A | 0.9300 | C29B—H29B | 0.9300 |
C30A—H30A | 0.9300 | C30B—H30B | 0.9300 |
C31A—N1A | 1.453 (4) | C31B—N1B | 1.453 (3) |
C31A—C32A | 1.506 (4) | C31B—C32B | 1.501 (4) |
C31A—H31A | 0.9700 | C31B—H31C | 0.9700 |
C31A—H31B | 0.9700 | C31B—H31D | 0.9700 |
C32A—C33A | 1.379 (4) | C32B—C33B | 1.361 (4) |
C32A—C37A | 1.387 (4) | C32B—C37B | 1.383 (4) |
C33A—C34A | 1.378 (4) | C33B—C34B | 1.375 (4) |
C33A—H33A | 0.9300 | C33B—H33B | 0.9300 |
C34A—C35A | 1.370 (5) | C34B—C35B | 1.359 (5) |
C34A—H34A | 0.9300 | C34B—H34B | 0.9300 |
C35A—C36A | 1.366 (5) | C35B—C36B | 1.355 (5) |
C35A—H35A | 0.9300 | C35B—H35B | 0.9300 |
C36A—C37A | 1.375 (5) | C36B—C37B | 1.378 (5) |
C36A—H36A | 0.9300 | C36B—H36B | 0.9300 |
C37A—H37A | 0.9300 | C37B—H37B | 0.9300 |
C38A—O4A | 1.194 (5) | C38B—O4B | 1.209 (5) |
C38A—N2A | 1.406 (4) | C38B—N2B | 1.412 (4) |
C38A—C39A | 1.471 (6) | C38B—C39B | 1.474 (5) |
C39A—H39A | 0.9600 | C39B—H39D | 0.9600 |
C39A—H39B | 0.9600 | C39B—H39E | 0.9600 |
C39A—H39C | 0.9600 | C39B—H39F | 0.9600 |
C2A—C1A—C6A | 121.9 (3) | C2B—C1B—C6B | 121.6 (3) |
C2A—C1A—N1A | 128.3 (3) | C2B—C1B—N1B | 128.0 (3) |
C6A—C1A—N1A | 109.7 (2) | C6B—C1B—N1B | 110.3 (3) |
C1A—C2A—C3A | 117.5 (3) | C3B—C2B—C1B | 117.9 (3) |
C1A—C2A—H2A | 121.2 | C3B—C2B—H2B | 121.1 |
C3A—C2A—H2A | 121.2 | C1B—C2B—H2B | 121.1 |
C4A—C3A—C2A | 121.7 (3) | C2B—C3B—C4B | 121.3 (3) |
C4A—C3A—H3A | 119.2 | C2B—C3B—H3B | 119.4 |
C2A—C3A—H3A | 119.2 | C4B—C3B—H3B | 119.4 |
C3A—C4A—C5A | 120.3 (3) | C3B—C4B—C5B | 120.4 (3) |
C3A—C4A—H4A | 119.8 | C3B—C4B—H4B | 119.8 |
C5A—C4A—H4A | 119.8 | C5B—C4B—H4B | 119.8 |
C6A—C5A—C4A | 118.7 (3) | C6B—C5B—C4B | 119.1 (3) |
C6A—C5A—H5A | 120.6 | C6B—C5B—H5B | 120.5 |
C4A—C5A—H5A | 120.6 | C4B—C5B—H5B | 120.5 |
C5A—C6A—C1A | 119.7 (3) | C5B—C6B—C1B | 119.7 (3) |
C5A—C6A—C7A | 131.1 (3) | C5B—C6B—C7B | 131.5 (2) |
C1A—C6A—C7A | 109.0 (2) | C1B—C6B—C7B | 108.7 (2) |
O2A—C7A—C6A | 110.6 (2) | O2B—C7B—C6B | 111.2 (2) |
O2A—C7A—C8A | 112.2 (2) | O2B—C7B—C8B | 110.3 (2) |
C6A—C7A—C8A | 101.8 (2) | C6B—C7B—C8B | 101.6 (2) |
O2A—C7A—C11A | 104.76 (19) | O2B—C7B—C11B | 105.34 (19) |
C6A—C7A—C11A | 117.8 (2) | C6B—C7B—C11B | 117.6 (2) |
C8A—C7A—C11A | 109.9 (2) | C8B—C7B—C11B | 110.7 (2) |
O1A—C8A—N1A | 125.9 (3) | O1B—C8B—N1B | 125.6 (3) |
O1A—C8A—C7A | 126.3 (2) | O1B—C8B—C7B | 127.1 (3) |
N1A—C8A—C7A | 107.8 (2) | N1B—C8B—C7B | 107.2 (2) |
O2A—C9A—C25A | 108.3 (2) | O2B—C9B—C25B | 108.9 (2) |
O2A—C9A—C10A | 105.79 (18) | O2B—C9B—C10B | 102.9 (2) |
C25A—C9A—C10A | 114.0 (2) | C25B—C9B—C10B | 115.1 (2) |
O2A—C9A—H9A | 109.5 | O2B—C9B—H9B | 109.9 |
C25A—C9A—H9A | 109.5 | C25B—C9B—H9B | 109.9 |
C10A—C9A—H9A | 109.5 | C10B—C9B—H9B | 109.9 |
C19A—C10A—C9A | 114.8 (2) | C19B—C10B—C9B | 117.8 (2) |
C19A—C10A—C11A | 118.5 (2) | C19B—C10B—C11B | 117.3 (2) |
C9A—C10A—C11A | 104.73 (19) | C9B—C10B—C11B | 103.8 (2) |
C19A—C10A—H10A | 105.9 | C19B—C10B—H10B | 105.6 |
C9A—C10A—H10A | 105.9 | C9B—C10B—H10B | 105.6 |
C11A—C10A—H10A | 105.9 | C11B—C10B—H10B | 105.6 |
C12A—C11A—C18A | 101.7 (2) | C12B—C11B—C18B | 102.0 (2) |
C12A—C11A—C10A | 122.4 (2) | C12B—C11B—C10B | 119.6 (2) |
C18A—C11A—C10A | 108.9 (2) | C18B—C11B—C10B | 109.2 (2) |
C12A—C11A—C7A | 113.6 (2) | C12B—C11B—C7B | 114.8 (2) |
C18A—C11A—C7A | 106.7 (2) | C18B—C11B—C7B | 109.5 (2) |
C10A—C11A—C7A | 102.75 (19) | C10B—C11B—C7B | 101.7 (2) |
C13A—C12A—C17A | 118.9 (3) | C13B—C12B—C17B | 119.5 (3) |
C13A—C12A—C11A | 131.5 (2) | C13B—C12B—C11B | 130.8 (3) |
C17A—C12A—C11A | 109.6 (2) | C17B—C12B—C11B | 109.7 (2) |
C12A—C13A—C14A | 119.9 (3) | C12B—C13B—C14B | 119.3 (3) |
C12A—C13A—H13A | 120.0 | C12B—C13B—H13B | 120.3 |
C14A—C13A—H13A | 120.0 | C14B—C13B—H13B | 120.3 |
C15A—C14A—C13A | 120.4 (3) | C15B—C14B—C13B | 120.3 (3) |
C15A—C14A—H14A | 119.8 | C15B—C14B—H14B | 119.8 |
C13A—C14A—H14A | 119.8 | C13B—C14B—H14B | 119.8 |
C14A—C15A—C16A | 121.6 (3) | C14B—C15B—C16B | 122.0 (3) |
C14A—C15A—H15A | 119.2 | C14B—C15B—H15B | 119.0 |
C16A—C15A—H15A | 119.2 | C16B—C15B—H15B | 119.0 |
C15A—C16A—C17A | 117.7 (3) | C15B—C16B—C17B | 117.4 (3) |
C15A—C16A—H16A | 121.2 | C15B—C16B—H16B | 121.3 |
C17A—C16A—H16A | 121.2 | C17B—C16B—H16B | 121.3 |
C16A—C17A—C12A | 121.5 (3) | C12B—C17B—C16B | 121.4 (3) |
C16A—C17A—N2A | 129.2 (3) | C12B—C17B—N2B | 110.0 (2) |
C12A—C17A—N2A | 109.3 (2) | C16B—C17B—N2B | 128.6 (3) |
O3A—C18A—N2A | 126.5 (3) | O3B—C18B—N2B | 125.9 (3) |
O3A—C18A—C11A | 125.3 (3) | O3B—C18B—C11B | 125.5 (3) |
N2A—C18A—C11A | 108.2 (3) | N2B—C18B—C11B | 108.6 (2) |
C24A—C19A—C20A | 117.5 (3) | C20B—C19B—C24B | 117.5 (3) |
C24A—C19A—C10A | 119.4 (2) | C20B—C19B—C10B | 123.3 (2) |
C20A—C19A—C10A | 122.9 (2) | C24B—C19B—C10B | 119.2 (2) |
C21A—C20A—C19A | 121.3 (3) | C19B—C20B—C21B | 121.0 (3) |
C21A—C20A—H20A | 119.4 | C19B—C20B—H20B | 119.5 |
C19A—C20A—H20A | 119.4 | C21B—C20B—H20B | 119.5 |
C22A—C21A—C20A | 120.5 (3) | C22B—C21B—C20B | 120.3 (3) |
C22A—C21A—H21A | 119.7 | C22B—C21B—H21B | 119.8 |
C20A—C21A—H21A | 119.7 | C20B—C21B—H21B | 119.8 |
C21A—C22A—C23A | 119.5 (3) | C23B—C22B—C21B | 119.6 (3) |
C21A—C22A—H22A | 120.2 | C23B—C22B—H22B | 120.2 |
C23A—C22A—H22A | 120.2 | C21B—C22B—H22B | 120.2 |
C22A—C23A—C24A | 120.5 (3) | C22B—C23B—C24B | 120.3 (3) |
C22A—C23A—H23A | 119.8 | C22B—C23B—H23B | 119.8 |
C24A—C23A—H23A | 119.8 | C24B—C23B—H23B | 119.8 |
C19A—C24A—C23A | 120.7 (3) | C23B—C24B—C19B | 121.2 (3) |
C19A—C24A—H24A | 119.7 | C23B—C24B—H24B | 119.4 |
C23A—C24A—H24A | 119.7 | C19B—C24B—H24B | 119.4 |
C30A—C25A—C26A | 117.8 (3) | C26B—C25B—C30B | 118.0 (3) |
C30A—C25A—C9A | 121.5 (2) | C26B—C25B—C9B | 120.7 (3) |
C26A—C25A—C9A | 120.6 (3) | C30B—C25B—C9B | 121.3 (3) |
C25A—C26A—C27A | 120.6 (3) | C25B—C26B—C27B | 120.6 (3) |
C25A—C26A—H26A | 119.7 | C25B—C26B—H26B | 119.7 |
C27A—C26A—H26A | 119.7 | C27B—C26B—H26B | 119.7 |
C28A—C27A—C26A | 120.4 (3) | C28B—C27B—C26B | 120.4 (3) |
C28A—C27A—H27A | 119.8 | C28B—C27B—H27B | 119.8 |
C26A—C27A—H27A | 119.8 | C26B—C27B—H27B | 119.8 |
C27A—C28A—C29A | 119.5 (3) | C29B—C28B—C27B | 119.6 (3) |
C27A—C28A—H28A | 120.2 | C29B—C28B—H28B | 120.2 |
C29A—C28A—H28A | 120.2 | C27B—C28B—H28B | 120.2 |
C28A—C29A—C30A | 120.4 (4) | C28B—C29B—C30B | 120.2 (3) |
C28A—C29A—H29A | 119.8 | C28B—C29B—H29B | 119.9 |
C30A—C29A—H29A | 119.8 | C30B—C29B—H29B | 119.9 |
C25A—C30A—C29A | 121.1 (3) | C29B—C30B—C25B | 121.1 (3) |
C25A—C30A—H30A | 119.4 | C29B—C30B—H30B | 119.4 |
C29A—C30A—H30A | 119.4 | C25B—C30B—H30B | 119.4 |
N1A—C31A—C32A | 113.7 (3) | N1B—C31B—C32B | 115.0 (3) |
N1A—C31A—H31A | 108.8 | N1B—C31B—H31C | 108.5 |
C32A—C31A—H31A | 108.8 | C32B—C31B—H31C | 108.5 |
N1A—C31A—H31B | 108.8 | N1B—C31B—H31D | 108.5 |
C32A—C31A—H31B | 108.8 | C32B—C31B—H31D | 108.5 |
H31A—C31A—H31B | 107.7 | H31C—C31B—H31D | 107.5 |
C33A—C32A—C37A | 118.3 (3) | C33B—C32B—C37B | 118.1 (3) |
C33A—C32A—C31A | 121.7 (3) | C33B—C32B—C31B | 122.5 (3) |
C37A—C32A—C31A | 120.0 (3) | C37B—C32B—C31B | 119.4 (3) |
C34A—C33A—C32A | 120.4 (3) | C32B—C33B—C34B | 120.9 (3) |
C34A—C33A—H33A | 119.8 | C32B—C33B—H33B | 119.5 |
C32A—C33A—H33A | 119.8 | C34B—C33B—H33B | 119.5 |
C35A—C34A—C33A | 120.9 (4) | C35B—C34B—C33B | 120.7 (4) |
C35A—C34A—H34A | 119.6 | C35B—C34B—H34B | 119.6 |
C33A—C34A—H34A | 119.6 | C33B—C34B—H34B | 119.6 |
C36A—C35A—C34A | 119.1 (4) | C36B—C35B—C34B | 119.2 (4) |
C36A—C35A—H35A | 120.4 | C36B—C35B—H35B | 120.4 |
C34A—C35A—H35A | 120.4 | C34B—C35B—H35B | 120.4 |
C35A—C36A—C37A | 120.6 (3) | C35B—C36B—C37B | 120.5 (4) |
C35A—C36A—H36A | 119.7 | C35B—C36B—H36B | 119.7 |
C37A—C36A—H36A | 119.7 | C37B—C36B—H36B | 119.7 |
C36A—C37A—C32A | 120.7 (3) | C36B—C37B—C32B | 120.5 (4) |
C36A—C37A—H37A | 119.7 | C36B—C37B—H37B | 119.7 |
C32A—C37A—H37A | 119.7 | C32B—C37B—H37B | 119.7 |
O4A—C38A—N2A | 119.8 (4) | O4B—C38B—N2B | 117.9 (4) |
O4A—C38A—C39A | 122.0 (4) | O4B—C38B—C39B | 123.3 (4) |
N2A—C38A—C39A | 118.2 (4) | N2B—C38B—C39B | 118.8 (4) |
C38A—C39A—H39A | 109.5 | C38B—C39B—H39D | 109.5 |
C38A—C39A—H39B | 109.5 | C38B—C39B—H39E | 109.5 |
H39A—C39A—H39B | 109.5 | H39D—C39B—H39E | 109.5 |
C38A—C39A—H39C | 109.5 | C38B—C39B—H39F | 109.5 |
H39A—C39A—H39C | 109.5 | H39D—C39B—H39F | 109.5 |
H39B—C39A—H39C | 109.5 | H39E—C39B—H39F | 109.5 |
C8A—N1A—C1A | 110.9 (2) | C8B—N1B—C1B | 110.7 (2) |
C8A—N1A—C31A | 124.1 (3) | C8B—N1B—C31B | 122.3 (3) |
C1A—N1A—C31A | 124.5 (2) | C1B—N1B—C31B | 124.8 (2) |
C18A—N2A—C38A | 125.8 (3) | C18B—N2B—C38B | 125.7 (3) |
C18A—N2A—C17A | 109.3 (2) | C18B—N2B—C17B | 108.7 (2) |
C38A—N2A—C17A | 124.9 (3) | C38B—N2B—C17B | 125.4 (3) |
C7A—O2A—C9A | 109.07 (18) | C7B—O2B—C9B | 107.58 (19) |
C6A—C1A—C2A—C3A | 2.1 (4) | C6B—C1B—C2B—C3B | −3.6 (5) |
N1A—C1A—C2A—C3A | −175.1 (3) | N1B—C1B—C2B—C3B | 171.1 (3) |
C1A—C2A—C3A—C4A | 0.4 (5) | C1B—C2B—C3B—C4B | 0.6 (6) |
C2A—C3A—C4A—C5A | −1.1 (5) | C2B—C3B—C4B—C5B | 1.8 (7) |
C3A—C4A—C5A—C6A | −0.6 (5) | C3B—C4B—C5B—C6B | −1.1 (6) |
C4A—C5A—C6A—C1A | 3.1 (4) | C4B—C5B—C6B—C1B | −1.8 (5) |
C4A—C5A—C6A—C7A | 178.0 (3) | C4B—C5B—C6B—C7B | −176.9 (4) |
C2A—C1A—C6A—C5A | −3.9 (4) | C2B—C1B—C6B—C5B | 4.3 (5) |
N1A—C1A—C6A—C5A | 173.8 (2) | N1B—C1B—C6B—C5B | −171.3 (3) |
C2A—C1A—C6A—C7A | −179.9 (3) | C2B—C1B—C6B—C7B | −179.6 (3) |
N1A—C1A—C6A—C7A | −2.2 (3) | N1B—C1B—C6B—C7B | 4.8 (3) |
C5A—C6A—C7A—O2A | −49.2 (4) | C5B—C6B—C7B—O2B | 47.8 (4) |
C1A—C6A—C7A—O2A | 126.2 (2) | C1B—C6B—C7B—O2B | −127.7 (2) |
C5A—C6A—C7A—C8A | −168.6 (3) | C5B—C6B—C7B—C8B | 165.2 (3) |
C1A—C6A—C7A—C8A | 6.8 (3) | C1B—C6B—C7B—C8B | −10.3 (3) |
C5A—C6A—C7A—C11A | 71.2 (4) | C5B—C6B—C7B—C11B | −73.7 (4) |
C1A—C6A—C7A—C11A | −113.4 (3) | C1B—C6B—C7B—C11B | 110.8 (3) |
O2A—C7A—C8A—O1A | 52.8 (4) | O2B—C7B—C8B—O1B | −47.7 (4) |
C6A—C7A—C8A—O1A | 171.1 (3) | C6B—C7B—C8B—O1B | −165.8 (3) |
C11A—C7A—C8A—O1A | −63.3 (3) | C11B—C7B—C8B—O1B | 68.5 (4) |
O2A—C7A—C8A—N1A | −127.5 (2) | O2B—C7B—C8B—N1B | 130.5 (2) |
C6A—C7A—C8A—N1A | −9.2 (3) | C6B—C7B—C8B—N1B | 12.4 (3) |
C11A—C7A—C8A—N1A | 116.4 (2) | C11B—C7B—C8B—N1B | −113.3 (2) |
O2A—C9A—C10A—C19A | 150.0 (2) | O2B—C9B—C10B—C19B | −168.83 (19) |
C25A—C9A—C10A—C19A | −91.1 (3) | C25B—C9B—C10B—C19B | 72.9 (3) |
O2A—C9A—C10A—C11A | 18.2 (2) | O2B—C9B—C10B—C11B | −37.2 (2) |
C25A—C9A—C10A—C11A | 137.1 (2) | C25B—C9B—C10B—C11B | −155.5 (2) |
C19A—C10A—C11A—C12A | 2.0 (3) | C19B—C10B—C11B—C12B | 21.6 (3) |
C9A—C10A—C11A—C12A | 131.6 (2) | C9B—C10B—C11B—C12B | −110.2 (3) |
C19A—C10A—C11A—C18A | 120.1 (2) | C19B—C10B—C11B—C18B | −95.2 (3) |
C9A—C10A—C11A—C18A | −110.4 (2) | C9B—C10B—C11B—C18B | 133.0 (2) |
C19A—C10A—C11A—C7A | −127.0 (2) | C19B—C10B—C11B—C7B | 149.2 (2) |
C9A—C10A—C11A—C7A | 2.5 (2) | C9B—C10B—C11B—C7B | 17.3 (2) |
O2A—C7A—C11A—C12A | −157.1 (2) | O2B—C7B—C11B—C12B | 139.0 (2) |
C6A—C7A—C11A—C12A | 79.5 (3) | C6B—C7B—C11B—C12B | −96.5 (3) |
C8A—C7A—C11A—C12A | −36.4 (3) | C8B—C7B—C11B—C12B | 19.7 (3) |
O2A—C7A—C11A—C18A | 91.7 (2) | O2B—C7B—C11B—C18B | −107.1 (2) |
C6A—C7A—C11A—C18A | −31.7 (3) | C6B—C7B—C11B—C18B | 17.5 (3) |
C8A—C7A—C11A—C18A | −147.6 (2) | C8B—C7B—C11B—C18B | 133.6 (2) |
O2A—C7A—C11A—C10A | −22.9 (2) | O2B—C7B—C11B—C10B | 8.3 (2) |
C6A—C7A—C11A—C10A | −146.2 (2) | C6B—C7B—C11B—C10B | 132.9 (2) |
C8A—C7A—C11A—C10A | 97.9 (2) | C8B—C7B—C11B—C10B | −110.9 (2) |
C18A—C11A—C12A—C13A | −170.2 (3) | C18B—C11B—C12B—C13B | 172.2 (3) |
C10A—C11A—C12A—C13A | −48.6 (4) | C10B—C11B—C12B—C13B | 51.8 (4) |
C7A—C11A—C12A—C13A | 75.6 (3) | C7B—C11B—C12B—C13B | −69.5 (3) |
C18A—C11A—C12A—C17A | 11.3 (3) | C18B—C11B—C12B—C17B | −8.6 (3) |
C10A—C11A—C12A—C17A | 132.9 (2) | C10B—C11B—C12B—C17B | −129.1 (2) |
C7A—C11A—C12A—C17A | −102.9 (2) | C7B—C11B—C12B—C17B | 109.7 (3) |
C17A—C12A—C13A—C14A | 0.2 (4) | C17B—C12B—C13B—C14B | −1.5 (4) |
C11A—C12A—C13A—C14A | −178.2 (3) | C11B—C12B—C13B—C14B | 177.6 (3) |
C12A—C13A—C14A—C15A | 0.9 (5) | C12B—C13B—C14B—C15B | 0.2 (4) |
C13A—C14A—C15A—C16A | −1.0 (5) | C13B—C14B—C15B—C16B | 1.1 (5) |
C14A—C15A—C16A—C17A | 0.0 (5) | C14B—C15B—C16B—C17B | −1.0 (5) |
C15A—C16A—C17A—C12A | 1.2 (4) | C13B—C12B—C17B—C16B | 1.7 (4) |
C15A—C16A—C17A—N2A | −175.9 (3) | C11B—C12B—C17B—C16B | −177.6 (2) |
C13A—C12A—C17A—C16A | −1.3 (4) | C13B—C12B—C17B—N2B | −176.5 (2) |
C11A—C12A—C17A—C16A | 177.4 (2) | C11B—C12B—C17B—N2B | 4.2 (3) |
C13A—C12A—C17A—N2A | 176.3 (2) | C15B—C16B—C17B—C12B | −0.4 (4) |
C11A—C12A—C17A—N2A | −5.0 (3) | C15B—C16B—C17B—N2B | 177.4 (3) |
C12A—C11A—C18A—O3A | 166.5 (3) | C12B—C11B—C18B—O3B | −168.6 (3) |
C10A—C11A—C18A—O3A | 36.1 (4) | C10B—C11B—C18B—O3B | −41.2 (4) |
C7A—C11A—C18A—O3A | −74.2 (3) | C7B—C11B—C18B—O3B | 69.4 (3) |
C12A—C11A—C18A—N2A | −13.8 (3) | C12B—C11B—C18B—N2B | 10.1 (3) |
C10A—C11A—C18A—N2A | −144.3 (2) | C10B—C11B—C18B—N2B | 137.6 (2) |
C7A—C11A—C18A—N2A | 105.5 (2) | C7B—C11B—C18B—N2B | −111.9 (2) |
C9A—C10A—C19A—C24A | 137.1 (2) | C9B—C10B—C19B—C20B | 29.7 (3) |
C11A—C10A—C19A—C24A | −98.1 (3) | C11B—C10B—C19B—C20B | −95.5 (3) |
C9A—C10A—C19A—C20A | −39.0 (3) | C9B—C10B—C19B—C24B | −147.1 (2) |
C11A—C10A—C19A—C20A | 85.8 (3) | C11B—C10B—C19B—C24B | 87.7 (3) |
C24A—C19A—C20A—C21A | 0.6 (4) | C24B—C19B—C20B—C21B | 0.1 (4) |
C10A—C19A—C20A—C21A | 176.8 (3) | C10B—C19B—C20B—C21B | −176.8 (2) |
C19A—C20A—C21A—C22A | 0.2 (5) | C19B—C20B—C21B—C22B | 0.2 (4) |
C20A—C21A—C22A—C23A | −0.4 (6) | C20B—C21B—C22B—C23B | −0.5 (5) |
C21A—C22A—C23A—C24A | −0.1 (6) | C21B—C22B—C23B—C24B | 0.4 (5) |
C20A—C19A—C24A—C23A | −1.2 (4) | C22B—C23B—C24B—C19B | −0.1 (5) |
C10A—C19A—C24A—C23A | −177.5 (3) | C20B—C19B—C24B—C23B | −0.2 (4) |
C22A—C23A—C24A—C19A | 0.9 (5) | C10B—C19B—C24B—C23B | 176.8 (3) |
O2A—C9A—C25A—C30A | 32.3 (4) | O2B—C9B—C25B—C26B | 123.7 (3) |
C10A—C9A—C25A—C30A | −85.2 (3) | C10B—C9B—C25B—C26B | −121.4 (3) |
O2A—C9A—C25A—C26A | −148.5 (2) | O2B—C9B—C25B—C30B | −56.5 (3) |
C10A—C9A—C25A—C26A | 94.0 (3) | C10B—C9B—C25B—C30B | 58.4 (4) |
C30A—C25A—C26A—C27A | 0.9 (4) | C30B—C25B—C26B—C27B | −0.5 (5) |
C9A—C25A—C26A—C27A | −178.3 (3) | C9B—C25B—C26B—C27B | 179.4 (3) |
C25A—C26A—C27A—C28A | −1.1 (5) | C25B—C26B—C27B—C28B | 0.9 (5) |
C26A—C27A—C28A—C29A | 0.3 (6) | C26B—C27B—C28B—C29B | −0.6 (6) |
C27A—C28A—C29A—C30A | 0.7 (6) | C27B—C28B—C29B—C30B | −0.1 (6) |
C26A—C25A—C30A—C29A | 0.0 (5) | C28B—C29B—C30B—C25B | 0.6 (5) |
C9A—C25A—C30A—C29A | 179.3 (3) | C26B—C25B—C30B—C29B | −0.3 (5) |
C28A—C29A—C30A—C25A | −0.8 (7) | C9B—C25B—C30B—C29B | 179.9 (3) |
N1A—C31A—C32A—C33A | −29.9 (5) | N1B—C31B—C32B—C33B | 13.0 (4) |
N1A—C31A—C32A—C37A | 150.9 (3) | N1B—C31B—C32B—C37B | −169.7 (3) |
C37A—C32A—C33A—C34A | −0.1 (5) | C37B—C32B—C33B—C34B | −0.9 (5) |
C31A—C32A—C33A—C34A | −179.2 (3) | C31B—C32B—C33B—C34B | 176.4 (3) |
C32A—C33A—C34A—C35A | 0.1 (5) | C32B—C33B—C34B—C35B | 0.0 (6) |
C33A—C34A—C35A—C36A | 0.1 (5) | C33B—C34B—C35B—C36B | 0.8 (7) |
C34A—C35A—C36A—C37A | −0.4 (5) | C34B—C35B—C36B—C37B | −0.7 (7) |
C35A—C36A—C37A—C32A | 0.4 (5) | C35B—C36B—C37B—C32B | −0.2 (6) |
C33A—C32A—C37A—C36A | −0.2 (5) | C33B—C32B—C37B—C36B | 1.0 (5) |
C31A—C32A—C37A—C36A | 179.0 (3) | C31B—C32B—C37B—C36B | −176.4 (3) |
O1A—C8A—N1A—C1A | −171.7 (3) | O1B—C8B—N1B—C1B | 167.8 (3) |
C7A—C8A—N1A—C1A | 8.6 (3) | C7B—C8B—N1B—C1B | −10.4 (3) |
O1A—C8A—N1A—C31A | 0.1 (5) | O1B—C8B—N1B—C31B | 4.0 (4) |
C7A—C8A—N1A—C31A | −179.6 (2) | C7B—C8B—N1B—C31B | −174.2 (2) |
C2A—C1A—N1A—C8A | 173.2 (3) | C2B—C1B—N1B—C8B | −171.4 (3) |
C6A—C1A—N1A—C8A | −4.2 (3) | C6B—C1B—N1B—C8B | 3.8 (3) |
C2A—C1A—N1A—C31A | 1.5 (5) | C2B—C1B—N1B—C31B | −8.1 (5) |
C6A—C1A—N1A—C31A | −176.0 (3) | C6B—C1B—N1B—C31B | 167.1 (3) |
C32A—C31A—N1A—C8A | 127.3 (3) | C32B—C31B—N1B—C8B | −108.1 (3) |
C32A—C31A—N1A—C1A | −62.0 (4) | C32B—C31B—N1B—C1B | 90.5 (3) |
O3A—C18A—N2A—C38A | 11.6 (5) | O3B—C18B—N2B—C38B | −4.8 (5) |
C11A—C18A—N2A—C38A | −168.0 (3) | C11B—C18B—N2B—C38B | 176.5 (3) |
O3A—C18A—N2A—C17A | −168.6 (3) | O3B—C18B—N2B—C17B | 170.5 (3) |
C11A—C18A—N2A—C17A | 11.8 (3) | C11B—C18B—N2B—C17B | −8.2 (3) |
O4A—C38A—N2A—C18A | −178.5 (4) | O4B—C38B—N2B—C18B | 173.9 (3) |
C39A—C38A—N2A—C18A | 2.5 (6) | C39B—C38B—N2B—C18B | −7.4 (5) |
O4A—C38A—N2A—C17A | 1.8 (6) | O4B—C38B—N2B—C17B | −0.6 (5) |
C39A—C38A—N2A—C17A | −177.2 (4) | C39B—C38B—N2B—C17B | 178.1 (3) |
C16A—C17A—N2A—C18A | 173.0 (3) | C12B—C17B—N2B—C18B | 2.6 (3) |
C12A—C17A—N2A—C18A | −4.4 (3) | C16B—C17B—N2B—C18B | −175.4 (3) |
C16A—C17A—N2A—C38A | −7.3 (5) | C12B—C17B—N2B—C38B | 177.9 (3) |
C12A—C17A—N2A—C38A | 175.4 (3) | C16B—C17B—N2B—C38B | 0.0 (5) |
C6A—C7A—O2A—C9A | 164.6 (2) | C6B—C7B—O2B—C9B | −161.6 (2) |
C8A—C7A—O2A—C9A | −82.5 (2) | C8B—C7B—O2B—C9B | 86.4 (2) |
C11A—C7A—O2A—C9A | 36.7 (2) | C11B—C7B—O2B—C9B | −33.1 (3) |
C25A—C9A—O2A—C7A | −157.9 (2) | C25B—C9B—O2B—C7B | 167.6 (2) |
C10A—C9A—O2A—C7A | −35.4 (2) | C10B—C9B—O2B—C7B | 45.0 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5A—H5A···O3A | 0.93 | 2.53 | 3.109 (4) | 121 |
C5B—H5B···O3B | 0.93 | 2.53 | 2.973 (4) | 109 |
C9A—H9A···O1A | 0.98 | 2.61 | 3.115 (3) | 112 |
C9B—H9B···O1B | 0.98 | 2.53 | 3.125 (3) | 119 |
C10A—H10A···O3A | 0.98 | 2.38 | 2.876 (3) | 111 |
C10B—H10B···O3B | 0.98 | 2.39 | 2.910 (3) | 113 |
C13A—H13A···O1A | 0.93 | 2.53 | 3.057 (4) | 116 |
C13B—H13B···O1B | 0.93 | 2.42 | 2.880 (4) | 110 |
C16A—H16A···O4A | 0.93 | 2.31 | 2.853 (6) | 116 |
C16B—H16B···O4B | 0.93 | 2.27 | 2.813 (5) | 117 |
C27A—H27A···O1Ai | 0.93 | 2.46 | 3.310 (4) | 152 |
C31A—H31A···O1A | 0.97 | 2.51 | 2.892 (4) | 103 |
C31B—H31D···O1B | 0.97 | 2.49 | 2.866 (4) | 103 |
C3A—H3A···Cg1(C19B–C24B)ii | 0.93 | 2.98 | 3.474 (4) | 115 |
C24A—H24A···Cg2(C32B–C37B)iii | 0.93 | 2.86 | 3.677 (3) | 147 |
C31B—H31C···Cg3(C25A–C30A)iv | 0.97 | 2.96 | 3.889 (4) | 161 |
C33A—H33A···Cg4(C12A–C17A) | 0.93 | 2.72 | 3.602 (4) | 158 |
C33B—H33B···Cg5(C12B–C17B) | 0.93 | 2.80 | 3.572 (4) | 142 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x+1, y+1, z; (iii) x, y, z+1; (iv) x, y, z−1. |
C39H30N2O4·0.5C2H3N | F(000) = 1284 |
Mr = 611.18 | Dx = 1.287 Mg m−3 |
Triclinic, P1 | Melting point: 456 K |
a = 9.6940 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 18.581 (1) Å | Cell parameters from 5108 reflections |
c = 20.1552 (11) Å | θ = 2.2–25.4° |
α = 114.872 (2)° | µ = 0.08 mm−1 |
β = 98.465 (2)° | T = 294 K |
γ = 99.397 (2)° | Plate, colorless |
V = 3153.6 (3) Å3 | 0.18 × 0.08 × 0.07 mm |
Z = 4 |
Bruker SMART APEX CCD area-detector diffractometer | 10357 reflections with I > 2σ(I) |
ω scans | Rint = 0.023 |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | θmax = 28.4°, θmin = 2.0° |
Tmin = 0.97, Tmax = 0.99 | h = −12→12 |
37306 measured reflections | k = −24→24 |
14817 independent reflections | l = −26→26 |
Refinement on F2 | 70 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.058 | H-atom parameters constrained |
wR(F2) = 0.147 | w = 1/[σ2(Fo2) + (0.063P)2 + 0.6698P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
14817 reflections | Δρmax = 0.27 e Å−3 |
870 parameters | Δρmin = −0.16 e Å−3 |
C39H30N2O4·0.5C2H3N | γ = 99.397 (2)° |
Mr = 611.18 | V = 3153.6 (3) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.6940 (5) Å | Mo Kα radiation |
b = 18.581 (1) Å | µ = 0.08 mm−1 |
c = 20.1552 (11) Å | T = 294 K |
α = 114.872 (2)° | 0.18 × 0.08 × 0.07 mm |
β = 98.465 (2)° |
Bruker SMART APEX CCD area-detector diffractometer | 14817 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 10357 reflections with I > 2σ(I) |
Tmin = 0.97, Tmax = 0.99 | Rint = 0.023 |
37306 measured reflections |
R[F2 > 2σ(F2)] = 0.058 | 70 restraints |
wR(F2) = 0.147 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.27 e Å−3 |
14817 reflections | Δρmin = −0.16 e Å−3 |
870 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1A | 0.9684 (2) | 0.65838 (11) | 0.32254 (10) | 0.0561 (4) | |
C2A | 0.9436 (3) | 0.64022 (14) | 0.38003 (12) | 0.0760 (6) | |
H2A | 1.0181 | 0.6525 | 0.4209 | 0.091* | |
C3A | 0.8050 (3) | 0.60335 (17) | 0.37481 (14) | 0.0917 (8) | |
H3A | 0.7854 | 0.5901 | 0.4127 | 0.110* | |
C4A | 0.6949 (3) | 0.58568 (17) | 0.31487 (14) | 0.0916 (8) | |
H4A | 0.6024 | 0.5592 | 0.3119 | 0.110* | |
C5A | 0.7200 (2) | 0.60684 (14) | 0.25858 (11) | 0.0713 (6) | |
H5A | 0.6447 | 0.5957 | 0.2185 | 0.086* | |
C6A | 0.85713 (19) | 0.64438 (11) | 0.26309 (9) | 0.0526 (4) | |
C7A | 0.91975 (18) | 0.67156 (10) | 0.21094 (9) | 0.0469 (4) | |
C8A | 1.08417 (19) | 0.68973 (10) | 0.24370 (10) | 0.0509 (4) | |
C9A | 0.90133 (18) | 0.64440 (10) | 0.08683 (9) | 0.0470 (4) | |
H9A | 1.0046 | 0.6633 | 0.0920 | 0.056* | |
C10A | 0.83557 (17) | 0.71791 (10) | 0.11803 (8) | 0.0443 (4) | |
H10A | 0.7311 | 0.6947 | 0.1033 | 0.053* | |
C11A | 0.87964 (17) | 0.75002 (10) | 0.20514 (9) | 0.0446 (4) | |
C12A | 0.99083 (18) | 0.83002 (10) | 0.25514 (9) | 0.0468 (4) | |
C13A | 1.12463 (19) | 0.86160 (11) | 0.24904 (10) | 0.0562 (4) | |
H13A | 1.1600 | 0.8321 | 0.2080 | 0.067* | |
C14A | 1.2057 (2) | 0.93768 (13) | 0.30461 (13) | 0.0704 (6) | |
H14A | 1.2952 | 0.9597 | 0.3003 | 0.084* | |
C15A | 1.1555 (3) | 0.98076 (13) | 0.36579 (13) | 0.0780 (6) | |
H15A | 1.2125 | 1.0313 | 0.4029 | 0.094* | |
C16A | 1.0229 (3) | 0.95099 (12) | 0.37356 (11) | 0.0719 (6) | |
H16A | 0.9892 | 0.9804 | 0.4153 | 0.086* | |
C17A | 0.9407 (2) | 0.87550 (11) | 0.31709 (10) | 0.0545 (4) | |
C18A | 0.7489 (2) | 0.76548 (12) | 0.23796 (10) | 0.0540 (4) | |
C19A | 0.86030 (17) | 0.77899 (10) | 0.08723 (8) | 0.0446 (4) | |
C20A | 0.98645 (19) | 0.80060 (11) | 0.06850 (10) | 0.0549 (4) | |
H20A | 1.0624 | 0.7779 | 0.0759 | 0.066* | |
C21A | 1.0017 (2) | 0.85567 (13) | 0.03879 (11) | 0.0664 (5) | |
H21A | 1.0884 | 0.8707 | 0.0278 | 0.080* | |
C22A | 0.8896 (3) | 0.88804 (13) | 0.02553 (13) | 0.0731 (6) | |
H22A | 0.8996 | 0.9246 | 0.0051 | 0.088* | |
C23A | 0.7632 (3) | 0.86616 (13) | 0.04255 (13) | 0.0742 (6) | |
H23A | 0.6866 | 0.8877 | 0.0333 | 0.089* | |
C24A | 0.7482 (2) | 0.81247 (12) | 0.07332 (11) | 0.0595 (5) | |
H24A | 0.6615 | 0.7985 | 0.0849 | 0.071* | |
C25A | 0.82953 (19) | 0.58155 (10) | 0.00694 (9) | 0.0503 (4) | |
C26A | 0.9095 (2) | 0.55844 (13) | −0.04589 (11) | 0.0683 (5) | |
H26A | 1.0081 | 0.5819 | −0.0322 | 0.082* | |
C27A | 0.8442 (3) | 0.50041 (15) | −0.11946 (12) | 0.0866 (7) | |
H27A | 0.8989 | 0.4857 | −0.1550 | 0.104* | |
C28A | 0.7002 (3) | 0.46481 (14) | −0.14000 (12) | 0.0839 (7) | |
H28A | 0.6567 | 0.4256 | −0.1894 | 0.101* | |
C29A | 0.6206 (3) | 0.48690 (13) | −0.08796 (12) | 0.0778 (6) | |
H29A | 0.5224 | 0.4625 | −0.1018 | 0.093* | |
C30A | 0.6841 (2) | 0.54524 (12) | −0.01472 (10) | 0.0652 (5) | |
H30A | 0.6282 | 0.5602 | 0.0203 | 0.078* | |
C31A | 1.2406 (2) | 0.69401 (12) | 0.35488 (12) | 0.0680 (5) | |
H31A | 1.3092 | 0.6882 | 0.3236 | 0.082* | |
H31B | 1.2317 | 0.6490 | 0.3678 | 0.082* | |
C32A | 1.29944 (19) | 0.77276 (12) | 0.42587 (10) | 0.0554 (4) | |
C33A | 1.2547 (2) | 0.84198 (13) | 0.43622 (11) | 0.0693 (5) | |
H33A | 1.1802 | 0.8397 | 0.4000 | 0.083* | |
C34A | 1.3190 (3) | 0.91521 (15) | 0.49984 (13) | 0.0864 (7) | |
H34A | 1.2880 | 0.9619 | 0.5060 | 0.104* | |
C35A | 1.4274 (3) | 0.91944 (17) | 0.55347 (13) | 0.0895 (7) | |
H35A | 1.4710 | 0.9691 | 0.5960 | 0.107* | |
C36A | 1.4720 (2) | 0.85102 (18) | 0.54491 (13) | 0.0862 (7) | |
H36A | 1.5452 | 0.8537 | 0.5820 | 0.103* | |
C37A | 1.4091 (2) | 0.77794 (15) | 0.48163 (12) | 0.0713 (6) | |
H37A | 1.4404 | 0.7314 | 0.4761 | 0.086* | |
C38A | 0.7195 (3) | 0.85912 (17) | 0.36535 (16) | 0.0970 (8) | |
C39A | 0.5626 (4) | 0.8226 (2) | 0.3428 (2) | 0.1603 (17) | |
H39A | 0.5447 | 0.7661 | 0.3325 | 0.240* | |
H39B | 0.5213 | 0.8263 | 0.2984 | 0.240* | |
H39C | 0.5199 | 0.8517 | 0.3829 | 0.240* | |
N1A | 1.10114 (16) | 0.68723 (9) | 0.31102 (8) | 0.0564 (4) | |
N2A | 0.79684 (18) | 0.83479 (10) | 0.30883 (9) | 0.0608 (4) | |
O1A | 1.17954 (14) | 0.70178 (8) | 0.21454 (8) | 0.0652 (3) | |
O2A | 0.87908 (13) | 0.60776 (7) | 0.13617 (6) | 0.0521 (3) | |
O3A | 0.62711 (14) | 0.72464 (9) | 0.20860 (8) | 0.0723 (4) | |
O4A | 0.7843 (3) | 0.90724 (14) | 0.42882 (12) | 0.1412 (9) | |
C1B | 0.4849 (2) | 0.65903 (10) | 0.82671 (9) | 0.0537 (4) | |
C2B | 0.5926 (3) | 0.66188 (12) | 0.88114 (11) | 0.0693 (6) | |
H2B | 0.5719 | 0.6538 | 0.9215 | 0.083* | |
C3B | 0.7314 (3) | 0.67709 (14) | 0.87397 (12) | 0.0759 (6) | |
H3B | 0.8060 | 0.6801 | 0.9106 | 0.091* | |
C4B | 0.7629 (2) | 0.68796 (13) | 0.81421 (12) | 0.0697 (6) | |
H4B | 0.8578 | 0.6967 | 0.8101 | 0.084* | |
C5B | 0.6540 (2) | 0.68606 (11) | 0.75968 (10) | 0.0572 (4) | |
H5B | 0.6750 | 0.6935 | 0.7191 | 0.069* | |
C6B | 0.51482 (19) | 0.67299 (10) | 0.76730 (9) | 0.0475 (4) | |
C7B | 0.37501 (17) | 0.66401 (9) | 0.71719 (8) | 0.0443 (4) | |
C8B | 0.2621 (2) | 0.63286 (10) | 0.75277 (10) | 0.0518 (4) | |
C9B | 0.25123 (17) | 0.61449 (10) | 0.59310 (9) | 0.0458 (4) | |
H9B | 0.1574 | 0.5849 | 0.5927 | 0.055* | |
C10B | 0.26023 (16) | 0.70760 (9) | 0.62721 (8) | 0.0419 (3) | |
H10B | 0.3237 | 0.7294 | 0.6028 | 0.050* | |
C11B | 0.34514 (16) | 0.74336 (9) | 0.71135 (8) | 0.0406 (3) | |
C12B | 0.29269 (18) | 0.79845 (10) | 0.77704 (9) | 0.0447 (4) | |
C13B | 0.1602 (2) | 0.79128 (11) | 0.79428 (10) | 0.0552 (4) | |
H13B | 0.0830 | 0.7473 | 0.7614 | 0.066* | |
C14B | 0.1428 (2) | 0.85019 (13) | 0.86104 (11) | 0.0639 (5) | |
H14B | 0.0536 | 0.8457 | 0.8728 | 0.077* | |
C15B | 0.2563 (3) | 0.91503 (12) | 0.90975 (11) | 0.0661 (5) | |
H15B | 0.2432 | 0.9536 | 0.9546 | 0.079* | |
C16B | 0.3895 (2) | 0.92413 (11) | 0.89358 (10) | 0.0619 (5) | |
H16B | 0.4661 | 0.9683 | 0.9267 | 0.074* | |
C17B | 0.40586 (19) | 0.86551 (10) | 0.82670 (9) | 0.0484 (4) | |
C18B | 0.49280 (17) | 0.79769 (10) | 0.72292 (9) | 0.0441 (4) | |
C19B | 0.11816 (18) | 0.72826 (10) | 0.61091 (9) | 0.0481 (4) | |
C20B | −0.0111 (2) | 0.68626 (13) | 0.61366 (11) | 0.0656 (5) | |
H20B | −0.0123 | 0.6444 | 0.6275 | 0.079* | |
C21B | −0.1384 (2) | 0.70601 (19) | 0.59602 (13) | 0.0892 (8) | |
H21B | −0.2242 | 0.6776 | 0.5985 | 0.107* | |
C22B | −0.1392 (3) | 0.7668 (2) | 0.57491 (15) | 0.1023 (9) | |
H22B | −0.2251 | 0.7799 | 0.5632 | 0.123* | |
C23B | −0.0129 (3) | 0.80844 (18) | 0.57104 (15) | 0.0936 (8) | |
H23B | −0.0132 | 0.8495 | 0.5562 | 0.112* | |
C24B | 0.1153 (2) | 0.78960 (13) | 0.58916 (11) | 0.0654 (5) | |
H24B | 0.2007 | 0.8185 | 0.5867 | 0.078* | |
C25B | 0.27754 (19) | 0.57783 (10) | 0.51526 (9) | 0.0476 (4) | |
C26B | 0.1647 (2) | 0.53842 (11) | 0.45255 (10) | 0.0624 (5) | |
H26B | 0.0705 | 0.5342 | 0.4581 | 0.075* | |
C27B | 0.1901 (3) | 0.50460 (12) | 0.38054 (11) | 0.0781 (7) | |
H27B | 0.1130 | 0.4782 | 0.3383 | 0.094* | |
C28B | 0.3270 (3) | 0.51026 (13) | 0.37210 (12) | 0.0784 (7) | |
H28B | 0.3439 | 0.4877 | 0.3242 | 0.094* | |
C29B | 0.4388 (3) | 0.54884 (17) | 0.43364 (13) | 0.0891 (7) | |
H29B | 0.5326 | 0.5524 | 0.4277 | 0.107* | |
C30B | 0.4153 (2) | 0.58296 (15) | 0.50496 (11) | 0.0736 (6) | |
H30B | 0.4935 | 0.6098 | 0.5466 | 0.088* | |
C31B | 0.2653 (3) | 0.61257 (13) | 0.86711 (12) | 0.0764 (6) | |
H31C | 0.2924 | 0.5638 | 0.8651 | 0.092* | |
H31D | 0.1616 | 0.5982 | 0.8480 | 0.092* | |
C32B | 0.3043 (2) | 0.67757 (12) | 0.94825 (11) | 0.0607 (5) | |
C33B | 0.3296 (2) | 0.75985 (13) | 0.96763 (11) | 0.0659 (5) | |
H33B | 0.3243 | 0.7767 | 0.9301 | 0.079* | |
C34B | 0.3627 (2) | 0.81737 (14) | 1.04203 (13) | 0.0737 (6) | |
H34B | 0.3798 | 0.8728 | 1.0545 | 0.088* | |
C35B | 0.3707 (2) | 0.79339 (18) | 1.09784 (13) | 0.0812 (7) | |
H35B | 0.3930 | 0.8325 | 1.1481 | 0.097* | |
C36B | 0.3458 (2) | 0.71209 (19) | 1.07974 (13) | 0.0801 (7) | |
H36B | 0.3507 | 0.6958 | 1.1176 | 0.096* | |
C37B | 0.3134 (2) | 0.65426 (15) | 1.00529 (12) | 0.0704 (6) | |
H37B | 0.2975 | 0.5990 | 0.9932 | 0.085* | |
C38B | 0.6661 (2) | 0.91889 (12) | 0.83376 (12) | 0.0682 (5) | |
C39B | 0.7802 (2) | 0.91494 (16) | 0.79147 (15) | 0.0959 (8) | |
H39D | 0.8655 | 0.9572 | 0.8235 | 0.144* | |
H39E | 0.7472 | 0.9227 | 0.7482 | 0.144* | |
H39F | 0.8015 | 0.8624 | 0.7754 | 0.144* | |
N1B | 0.33483 (18) | 0.63827 (9) | 0.81852 (8) | 0.0584 (4) | |
N2B | 0.52902 (15) | 0.86379 (8) | 0.79570 (8) | 0.0501 (3) | |
O1B | 0.13351 (15) | 0.60823 (8) | 0.72638 (8) | 0.0679 (4) | |
O2B | 0.36310 (12) | 0.60636 (7) | 0.64245 (6) | 0.0493 (3) | |
O3B | 0.56517 (13) | 0.78525 (8) | 0.67774 (7) | 0.0566 (3) | |
O4B | 0.68638 (19) | 0.96645 (11) | 0.89900 (9) | 0.1077 (6) | |
C40 | 0.1678 (18) | 0.9849 (10) | 0.7561 (8) | 0.116 (3) | 0.654 (19) |
H40A | 0.1530 | 1.0353 | 0.7916 | 0.175* | 0.654 (19) |
H40B | 0.1414 | 0.9430 | 0.7713 | 0.175* | 0.654 (19) |
H40C | 0.1093 | 0.9688 | 0.7070 | 0.175* | 0.654 (19) |
C41 | 0.3157 (15) | 0.9959 (6) | 0.7539 (6) | 0.116 (3) | 0.654 (19) |
N3 | 0.4317 (13) | 1.0040 (6) | 0.7503 (4) | 0.141 (2) | 0.654 (19) |
C401 | 0.145 (3) | 0.980 (2) | 0.7664 (17) | 0.110 (3) | 0.346 (19) |
H40D | 0.1046 | 0.9233 | 0.7317 | 0.165* | 0.346 (19) |
H40E | 0.0771 | 1.0111 | 0.7620 | 0.165* | 0.346 (19) |
H40F | 0.1671 | 0.9867 | 0.8169 | 0.165* | 0.346 (19) |
C411 | 0.279 (2) | 1.0104 (13) | 0.7484 (12) | 0.117 (3) | 0.346 (19) |
N31 | 0.386 (2) | 1.0335 (11) | 0.7393 (8) | 0.137 (4) | 0.346 (19) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1A | 0.0607 (11) | 0.0518 (10) | 0.0471 (10) | 0.0046 (8) | 0.0027 (8) | 0.0212 (8) |
C2A | 0.0857 (16) | 0.0852 (15) | 0.0537 (12) | 0.0080 (12) | 0.0018 (10) | 0.0381 (11) |
C3A | 0.0991 (19) | 0.114 (2) | 0.0736 (15) | 0.0059 (15) | 0.0215 (14) | 0.0612 (15) |
C4A | 0.0802 (16) | 0.114 (2) | 0.0795 (16) | −0.0117 (14) | 0.0156 (13) | 0.0569 (15) |
C5A | 0.0603 (12) | 0.0853 (15) | 0.0577 (12) | −0.0074 (10) | 0.0030 (9) | 0.0357 (11) |
C6A | 0.0543 (10) | 0.0520 (10) | 0.0429 (9) | 0.0020 (8) | 0.0036 (8) | 0.0203 (8) |
C7A | 0.0477 (9) | 0.0462 (9) | 0.0383 (8) | 0.0041 (7) | 0.0041 (7) | 0.0162 (7) |
C8A | 0.0516 (10) | 0.0402 (9) | 0.0509 (10) | 0.0084 (7) | 0.0063 (8) | 0.0147 (7) |
C9A | 0.0498 (9) | 0.0459 (9) | 0.0404 (8) | 0.0071 (7) | 0.0071 (7) | 0.0181 (7) |
C10A | 0.0370 (8) | 0.0482 (9) | 0.0388 (8) | 0.0043 (7) | 0.0037 (6) | 0.0158 (7) |
C11A | 0.0412 (8) | 0.0474 (9) | 0.0395 (8) | 0.0064 (7) | 0.0072 (7) | 0.0170 (7) |
C12A | 0.0509 (10) | 0.0440 (9) | 0.0401 (8) | 0.0089 (7) | 0.0036 (7) | 0.0175 (7) |
C13A | 0.0505 (10) | 0.0563 (10) | 0.0544 (10) | 0.0037 (8) | 0.0025 (8) | 0.0252 (9) |
C14A | 0.0611 (12) | 0.0622 (12) | 0.0739 (14) | −0.0060 (10) | −0.0070 (10) | 0.0334 (11) |
C15A | 0.0869 (16) | 0.0474 (11) | 0.0712 (14) | −0.0012 (11) | −0.0109 (12) | 0.0168 (10) |
C16A | 0.0974 (17) | 0.0508 (11) | 0.0532 (11) | 0.0234 (11) | 0.0062 (11) | 0.0127 (9) |
C17A | 0.0639 (11) | 0.0484 (10) | 0.0487 (10) | 0.0159 (8) | 0.0101 (8) | 0.0204 (8) |
C18A | 0.0507 (11) | 0.0631 (11) | 0.0498 (10) | 0.0140 (9) | 0.0140 (8) | 0.0267 (9) |
C19A | 0.0440 (9) | 0.0449 (9) | 0.0368 (8) | 0.0083 (7) | 0.0051 (7) | 0.0137 (7) |
C20A | 0.0487 (10) | 0.0645 (11) | 0.0554 (10) | 0.0158 (8) | 0.0116 (8) | 0.0305 (9) |
C21A | 0.0657 (12) | 0.0717 (13) | 0.0693 (13) | 0.0105 (10) | 0.0212 (10) | 0.0399 (11) |
C22A | 0.0903 (16) | 0.0645 (13) | 0.0782 (14) | 0.0232 (11) | 0.0211 (12) | 0.0434 (11) |
C23A | 0.0776 (15) | 0.0709 (13) | 0.0897 (15) | 0.0370 (11) | 0.0208 (12) | 0.0442 (12) |
C24A | 0.0530 (11) | 0.0624 (11) | 0.0646 (12) | 0.0199 (9) | 0.0151 (9) | 0.0281 (10) |
C25A | 0.0614 (11) | 0.0439 (9) | 0.0407 (9) | 0.0117 (8) | 0.0071 (8) | 0.0171 (7) |
C26A | 0.0667 (12) | 0.0666 (12) | 0.0592 (12) | 0.0230 (10) | 0.0174 (10) | 0.0142 (10) |
C27A | 0.104 (2) | 0.0803 (15) | 0.0563 (13) | 0.0365 (14) | 0.0276 (13) | 0.0058 (11) |
C28A | 0.1039 (19) | 0.0660 (13) | 0.0478 (12) | 0.0199 (13) | −0.0012 (12) | 0.0015 (10) |
C29A | 0.0784 (15) | 0.0697 (13) | 0.0549 (12) | −0.0039 (11) | −0.0053 (11) | 0.0152 (10) |
C30A | 0.0664 (12) | 0.0649 (12) | 0.0471 (10) | −0.0012 (10) | 0.0064 (9) | 0.0185 (9) |
C31A | 0.0588 (12) | 0.0605 (12) | 0.0766 (13) | 0.0127 (9) | −0.0063 (10) | 0.0317 (10) |
C32A | 0.0470 (10) | 0.0632 (11) | 0.0565 (10) | 0.0053 (8) | 0.0023 (8) | 0.0341 (9) |
C33A | 0.0689 (13) | 0.0668 (13) | 0.0592 (12) | 0.0145 (10) | −0.0071 (10) | 0.0250 (10) |
C34A | 0.0962 (18) | 0.0700 (14) | 0.0696 (14) | 0.0160 (12) | −0.0005 (13) | 0.0187 (12) |
C35A | 0.0848 (17) | 0.0905 (18) | 0.0590 (13) | −0.0051 (14) | −0.0063 (12) | 0.0197 (12) |
C36A | 0.0627 (13) | 0.121 (2) | 0.0629 (14) | −0.0017 (14) | −0.0115 (11) | 0.0484 (15) |
C37A | 0.0549 (11) | 0.0931 (16) | 0.0731 (13) | 0.0107 (11) | 0.0008 (10) | 0.0521 (13) |
C38A | 0.122 (2) | 0.0870 (17) | 0.0841 (18) | 0.0301 (16) | 0.0622 (17) | 0.0269 (15) |
C39A | 0.128 (3) | 0.166 (3) | 0.156 (3) | 0.014 (2) | 0.110 (3) | 0.029 (3) |
N1A | 0.0511 (9) | 0.0547 (9) | 0.0553 (9) | 0.0057 (7) | −0.0024 (7) | 0.0254 (7) |
N2A | 0.0694 (10) | 0.0628 (10) | 0.0520 (9) | 0.0225 (8) | 0.0255 (8) | 0.0223 (8) |
O1A | 0.0515 (7) | 0.0690 (8) | 0.0718 (9) | 0.0144 (6) | 0.0201 (7) | 0.0277 (7) |
O2A | 0.0638 (7) | 0.0436 (6) | 0.0391 (6) | 0.0050 (5) | 0.0043 (5) | 0.0156 (5) |
O3A | 0.0446 (7) | 0.0958 (11) | 0.0691 (9) | 0.0094 (7) | 0.0154 (6) | 0.0332 (8) |
O4A | 0.178 (2) | 0.1246 (17) | 0.0826 (14) | 0.0274 (16) | 0.0698 (15) | 0.0033 (12) |
C1B | 0.0722 (12) | 0.0414 (9) | 0.0421 (9) | 0.0146 (8) | 0.0061 (8) | 0.0166 (7) |
C2B | 0.0922 (17) | 0.0653 (12) | 0.0499 (11) | 0.0264 (11) | 0.0039 (10) | 0.0276 (10) |
C3B | 0.0847 (16) | 0.0747 (14) | 0.0567 (12) | 0.0324 (12) | −0.0092 (11) | 0.0232 (11) |
C4B | 0.0595 (12) | 0.0682 (13) | 0.0676 (13) | 0.0222 (10) | −0.0005 (10) | 0.0213 (11) |
C5B | 0.0573 (11) | 0.0573 (11) | 0.0524 (10) | 0.0193 (9) | 0.0092 (8) | 0.0203 (9) |
C6B | 0.0572 (10) | 0.0400 (8) | 0.0386 (8) | 0.0138 (7) | 0.0042 (7) | 0.0134 (7) |
C7B | 0.0501 (9) | 0.0410 (8) | 0.0363 (8) | 0.0094 (7) | 0.0071 (7) | 0.0143 (7) |
C8B | 0.0621 (11) | 0.0401 (9) | 0.0470 (9) | 0.0060 (8) | 0.0115 (8) | 0.0171 (7) |
C9B | 0.0430 (9) | 0.0443 (9) | 0.0415 (8) | 0.0057 (7) | 0.0050 (7) | 0.0153 (7) |
C10B | 0.0418 (8) | 0.0448 (8) | 0.0355 (8) | 0.0084 (7) | 0.0085 (6) | 0.0161 (7) |
C11B | 0.0412 (8) | 0.0406 (8) | 0.0370 (8) | 0.0089 (6) | 0.0085 (6) | 0.0157 (7) |
C12B | 0.0531 (10) | 0.0425 (8) | 0.0379 (8) | 0.0143 (7) | 0.0104 (7) | 0.0170 (7) |
C13B | 0.0578 (11) | 0.0598 (11) | 0.0477 (10) | 0.0171 (9) | 0.0167 (8) | 0.0221 (8) |
C14B | 0.0707 (13) | 0.0750 (13) | 0.0571 (11) | 0.0331 (11) | 0.0289 (10) | 0.0307 (10) |
C15B | 0.0971 (16) | 0.0577 (11) | 0.0474 (10) | 0.0345 (11) | 0.0266 (11) | 0.0193 (9) |
C16B | 0.0847 (14) | 0.0442 (10) | 0.0466 (10) | 0.0149 (9) | 0.0119 (9) | 0.0129 (8) |
C17B | 0.0599 (10) | 0.0413 (9) | 0.0430 (9) | 0.0136 (8) | 0.0098 (8) | 0.0187 (7) |
C18B | 0.0442 (9) | 0.0437 (9) | 0.0429 (8) | 0.0094 (7) | 0.0054 (7) | 0.0206 (7) |
C19B | 0.0476 (9) | 0.0527 (9) | 0.0361 (8) | 0.0153 (7) | 0.0076 (7) | 0.0130 (7) |
C20B | 0.0492 (11) | 0.0809 (14) | 0.0599 (11) | 0.0136 (10) | 0.0102 (9) | 0.0277 (10) |
C21B | 0.0476 (12) | 0.130 (2) | 0.0749 (15) | 0.0244 (13) | 0.0123 (11) | 0.0327 (15) |
C22B | 0.0742 (18) | 0.139 (3) | 0.0887 (18) | 0.0631 (18) | 0.0099 (14) | 0.0381 (18) |
C23B | 0.096 (2) | 0.1034 (19) | 0.0955 (18) | 0.0569 (16) | 0.0163 (15) | 0.0493 (16) |
C24B | 0.0659 (12) | 0.0688 (12) | 0.0637 (12) | 0.0277 (10) | 0.0120 (10) | 0.0296 (10) |
C25B | 0.0549 (10) | 0.0395 (8) | 0.0394 (8) | 0.0096 (7) | 0.0054 (7) | 0.0123 (7) |
C26B | 0.0635 (12) | 0.0592 (11) | 0.0498 (10) | −0.0049 (9) | 0.0003 (9) | 0.0228 (9) |
C27B | 0.1053 (19) | 0.0576 (12) | 0.0413 (10) | −0.0159 (12) | −0.0078 (11) | 0.0158 (9) |
C28B | 0.121 (2) | 0.0583 (12) | 0.0502 (12) | 0.0227 (13) | 0.0314 (13) | 0.0160 (10) |
C29B | 0.0911 (17) | 0.120 (2) | 0.0652 (15) | 0.0518 (16) | 0.0356 (13) | 0.0357 (14) |
C30B | 0.0608 (12) | 0.1007 (17) | 0.0489 (11) | 0.0267 (11) | 0.0119 (9) | 0.0226 (11) |
C31B | 0.1061 (17) | 0.0621 (12) | 0.0659 (13) | 0.0031 (12) | 0.0242 (12) | 0.0391 (11) |
C32B | 0.0637 (12) | 0.0713 (13) | 0.0570 (11) | 0.0140 (9) | 0.0185 (9) | 0.0381 (10) |
C33B | 0.0754 (13) | 0.0701 (13) | 0.0615 (12) | 0.0215 (10) | 0.0187 (10) | 0.0368 (11) |
C34B | 0.0642 (13) | 0.0769 (14) | 0.0745 (14) | 0.0231 (11) | 0.0230 (11) | 0.0256 (12) |
C35B | 0.0570 (13) | 0.118 (2) | 0.0595 (13) | 0.0228 (13) | 0.0221 (10) | 0.0286 (14) |
C36B | 0.0622 (13) | 0.133 (2) | 0.0632 (14) | 0.0225 (14) | 0.0210 (10) | 0.0597 (15) |
C37B | 0.0694 (13) | 0.0914 (15) | 0.0715 (14) | 0.0190 (11) | 0.0242 (11) | 0.0545 (13) |
C38B | 0.0636 (12) | 0.0548 (11) | 0.0627 (12) | −0.0038 (9) | −0.0015 (10) | 0.0171 (10) |
C39B | 0.0622 (14) | 0.0910 (17) | 0.0958 (18) | −0.0185 (12) | 0.0090 (13) | 0.0236 (14) |
N1B | 0.0738 (11) | 0.0539 (9) | 0.0466 (8) | 0.0068 (7) | 0.0125 (7) | 0.0261 (7) |
N2B | 0.0523 (8) | 0.0421 (7) | 0.0449 (8) | 0.0032 (6) | 0.0039 (6) | 0.0153 (6) |
O1B | 0.0567 (8) | 0.0704 (9) | 0.0660 (8) | −0.0048 (7) | 0.0092 (7) | 0.0304 (7) |
O2B | 0.0597 (7) | 0.0440 (6) | 0.0365 (6) | 0.0153 (5) | 0.0052 (5) | 0.0127 (5) |
O3B | 0.0473 (7) | 0.0670 (8) | 0.0521 (7) | 0.0089 (6) | 0.0154 (6) | 0.0248 (6) |
O4B | 0.0897 (12) | 0.0961 (12) | 0.0685 (10) | −0.0217 (10) | 0.0009 (9) | −0.0039 (9) |
C40 | 0.177 (6) | 0.090 (4) | 0.081 (4) | 0.035 (4) | 0.014 (4) | 0.043 (4) |
C41 | 0.175 (6) | 0.089 (3) | 0.081 (3) | 0.013 (4) | 0.017 (4) | 0.048 (2) |
N3 | 0.189 (6) | 0.122 (4) | 0.113 (3) | 0.014 (4) | 0.030 (4) | 0.064 (3) |
C401 | 0.162 (7) | 0.090 (5) | 0.083 (5) | 0.019 (5) | 0.021 (5) | 0.052 (4) |
C411 | 0.168 (7) | 0.096 (5) | 0.083 (4) | 0.016 (5) | 0.027 (5) | 0.042 (4) |
N31 | 0.178 (7) | 0.116 (6) | 0.104 (5) | 0.013 (5) | 0.032 (5) | 0.048 (4) |
C1A—C2A | 1.378 (3) | C3B—C4B | 1.370 (3) |
C1A—C6A | 1.390 (2) | C3B—H3B | 0.9300 |
C1A—N1A | 1.402 (2) | C4B—C5B | 1.392 (3) |
C2A—C3A | 1.372 (3) | C4B—H4B | 0.9300 |
C2A—H2A | 0.9300 | C5B—C6B | 1.375 (3) |
C3A—C4A | 1.371 (3) | C5B—H5B | 0.9300 |
C3A—H3A | 0.9300 | C6B—C7B | 1.505 (2) |
C4A—C5A | 1.388 (3) | C7B—O2B | 1.4074 (18) |
C4A—H4A | 0.9300 | C7B—C8B | 1.556 (2) |
C5A—C6A | 1.368 (3) | C7B—C11B | 1.596 (2) |
C5A—H5A | 0.9300 | C8B—O1B | 1.208 (2) |
C6A—C7A | 1.504 (2) | C8B—N1B | 1.361 (2) |
C7A—O2A | 1.4147 (19) | C9B—O2B | 1.4319 (19) |
C7A—C8A | 1.555 (2) | C9B—C25B | 1.505 (2) |
C7A—C11A | 1.614 (2) | C9B—C10B | 1.551 (2) |
C8A—O1A | 1.206 (2) | C9B—H9B | 0.9800 |
C8A—N1A | 1.364 (2) | C10B—C19B | 1.516 (2) |
C9A—O2A | 1.4434 (19) | C10B—C11B | 1.568 (2) |
C9A—C25A | 1.505 (2) | C10B—H10B | 0.9800 |
C9A—C10A | 1.532 (2) | C11B—C12B | 1.512 (2) |
C9A—H9A | 0.9800 | C11B—C18B | 1.534 (2) |
C10A—C19A | 1.509 (2) | C12B—C13B | 1.380 (2) |
C10A—C11A | 1.561 (2) | C12B—C17B | 1.393 (2) |
C10A—H10A | 0.9800 | C13B—C14B | 1.388 (3) |
C11A—C12A | 1.511 (2) | C13B—H13B | 0.9300 |
C11A—C18A | 1.527 (2) | C14B—C15B | 1.372 (3) |
C12A—C13A | 1.379 (2) | C14B—H14B | 0.9300 |
C12A—C17A | 1.391 (2) | C15B—C16B | 1.379 (3) |
C13A—C14A | 1.384 (3) | C15B—H15B | 0.9300 |
C13A—H13A | 0.9300 | C16B—C17B | 1.383 (2) |
C14A—C15A | 1.368 (3) | C16B—H16B | 0.9300 |
C14A—H14A | 0.9300 | C17B—N2B | 1.425 (2) |
C15A—C16A | 1.372 (3) | C18B—O3B | 1.1996 (19) |
C15A—H15A | 0.9300 | C18B—N2B | 1.406 (2) |
C16A—C17A | 1.386 (3) | C19B—C24B | 1.385 (3) |
C16A—H16A | 0.9300 | C19B—C20B | 1.386 (3) |
C17A—N2A | 1.424 (2) | C20B—C21B | 1.383 (3) |
C18A—O3A | 1.201 (2) | C20B—H20B | 0.9300 |
C18A—N2A | 1.406 (2) | C21B—C22B | 1.366 (4) |
C19A—C20A | 1.379 (2) | C21B—H21B | 0.9300 |
C19A—C24A | 1.387 (2) | C22B—C23B | 1.368 (4) |
C20A—C21A | 1.386 (3) | C22B—H22B | 0.9300 |
C20A—H20A | 0.9300 | C23B—C24B | 1.384 (3) |
C21A—C22A | 1.370 (3) | C23B—H23B | 0.9300 |
C21A—H21A | 0.9300 | C24B—H24B | 0.9300 |
C22A—C23A | 1.365 (3) | C25B—C26B | 1.372 (2) |
C22A—H22A | 0.9300 | C25B—C30B | 1.376 (3) |
C23A—C24A | 1.379 (3) | C26B—C27B | 1.397 (3) |
C23A—H23A | 0.9300 | C26B—H26B | 0.9300 |
C24A—H24A | 0.9300 | C27B—C28B | 1.355 (3) |
C25A—C26A | 1.374 (3) | C27B—H27B | 0.9300 |
C25A—C30A | 1.376 (3) | C28B—C29B | 1.353 (3) |
C26A—C27A | 1.385 (3) | C28B—H28B | 0.9300 |
C26A—H26A | 0.9300 | C29B—C30B | 1.377 (3) |
C27A—C28A | 1.362 (3) | C29B—H29B | 0.9300 |
C27A—H27A | 0.9300 | C30B—H30B | 0.9300 |
C28A—C29A | 1.358 (3) | C31B—N1B | 1.458 (2) |
C28A—H28A | 0.9300 | C31B—C32B | 1.511 (3) |
C29A—C30A | 1.379 (3) | C31B—H31C | 0.9700 |
C29A—H29A | 0.9300 | C31B—H31D | 0.9700 |
C30A—H30A | 0.9300 | C32B—C33B | 1.377 (3) |
C31A—N1A | 1.457 (2) | C32B—C37B | 1.385 (3) |
C31A—C32A | 1.497 (3) | C33B—C34B | 1.375 (3) |
C31A—H31A | 0.9700 | C33B—H33B | 0.9300 |
C31A—H31B | 0.9700 | C34B—C35B | 1.370 (3) |
C32A—C33A | 1.367 (3) | C34B—H34B | 0.9300 |
C32A—C37A | 1.388 (3) | C35B—C36B | 1.366 (4) |
C33A—C34A | 1.380 (3) | C35B—H35B | 0.9300 |
C33A—H33A | 0.9300 | C36B—C37B | 1.378 (3) |
C34A—C35A | 1.358 (3) | C36B—H36B | 0.9300 |
C34A—H34A | 0.9300 | C37B—H37B | 0.9300 |
C35A—C36A | 1.360 (4) | C38B—O4B | 1.199 (2) |
C35A—H35A | 0.9300 | C38B—N2B | 1.413 (2) |
C36A—C37A | 1.373 (3) | C38B—C39B | 1.485 (3) |
C36A—H36A | 0.9300 | C39B—H39D | 0.9600 |
C37A—H37A | 0.9300 | C39B—H39E | 0.9600 |
C38A—O4A | 1.204 (3) | C39B—H39F | 0.9600 |
C38A—N2A | 1.412 (3) | C40—C41 | 1.425 (11) |
C38A—C39A | 1.476 (4) | C40—H40A | 0.9600 |
C39A—H39A | 0.9600 | C40—H40B | 0.9600 |
C39A—H39B | 0.9600 | C40—H40C | 0.9600 |
C39A—H39C | 0.9600 | C41—N3 | 1.127 (9) |
C1B—C2B | 1.376 (3) | C401—C411 | 1.485 (17) |
C1B—C6B | 1.387 (2) | C401—H40D | 0.9600 |
C1B—N1B | 1.408 (2) | C401—H40E | 0.9600 |
C2B—C3B | 1.371 (3) | C401—H40F | 0.9600 |
C2B—H2B | 0.9300 | C411—N31 | 1.128 (15) |
C2A—C1A—C6A | 121.93 (19) | C4B—C3B—H3B | 119.2 |
C2A—C1A—N1A | 127.99 (18) | C2B—C3B—H3B | 119.2 |
C6A—C1A—N1A | 109.97 (15) | C3B—C4B—C5B | 120.5 (2) |
C3A—C2A—C1A | 117.6 (2) | C3B—C4B—H4B | 119.7 |
C3A—C2A—H2A | 121.2 | C5B—C4B—H4B | 119.7 |
C1A—C2A—H2A | 121.2 | C6B—C5B—C4B | 118.40 (19) |
C4A—C3A—C2A | 121.3 (2) | C6B—C5B—H5B | 120.8 |
C4A—C3A—H3A | 119.4 | C4B—C5B—H5B | 120.8 |
C2A—C3A—H3A | 119.4 | C5B—C6B—C1B | 120.01 (16) |
C3A—C4A—C5A | 120.7 (2) | C5B—C6B—C7B | 131.15 (16) |
C3A—C4A—H4A | 119.6 | C1B—C6B—C7B | 108.66 (15) |
C5A—C4A—H4A | 119.6 | O2B—C7B—C6B | 110.38 (13) |
C6A—C5A—C4A | 118.90 (19) | O2B—C7B—C8B | 111.72 (13) |
C6A—C5A—H5A | 120.6 | C6B—C7B—C8B | 101.88 (13) |
C4A—C5A—H5A | 120.6 | O2B—C7B—C11B | 104.88 (12) |
C5A—C6A—C1A | 119.45 (17) | C6B—C7B—C11B | 118.19 (13) |
C5A—C6A—C7A | 131.81 (16) | C8B—C7B—C11B | 109.94 (13) |
C1A—C6A—C7A | 108.63 (15) | O1B—C8B—N1B | 126.59 (17) |
O2A—C7A—C6A | 111.09 (13) | O1B—C8B—C7B | 125.91 (16) |
O2A—C7A—C8A | 110.17 (13) | N1B—C8B—C7B | 107.50 (15) |
C6A—C7A—C8A | 101.73 (13) | O2B—C9B—C25B | 107.71 (13) |
O2A—C7A—C11A | 105.43 (12) | O2B—C9B—C10B | 105.40 (12) |
C6A—C7A—C11A | 117.74 (14) | C25B—C9B—C10B | 114.39 (13) |
C8A—C7A—C11A | 110.66 (12) | O2B—C9B—H9B | 109.7 |
O1A—C8A—N1A | 125.92 (17) | C25B—C9B—H9B | 109.7 |
O1A—C8A—C7A | 126.73 (16) | C10B—C9B—H9B | 109.7 |
N1A—C8A—C7A | 107.33 (15) | C19B—C10B—C9B | 114.46 (13) |
O2A—C9A—C25A | 108.70 (13) | C19B—C10B—C11B | 118.57 (13) |
O2A—C9A—C10A | 102.21 (13) | C9B—C10B—C11B | 104.63 (12) |
C25A—C9A—C10A | 115.24 (14) | C19B—C10B—H10B | 106.1 |
O2A—C9A—H9A | 110.1 | C9B—C10B—H10B | 106.1 |
C25A—C9A—H9A | 110.1 | C11B—C10B—H10B | 106.1 |
C10A—C9A—H9A | 110.1 | C12B—C11B—C18B | 101.56 (12) |
C19A—C10A—C9A | 116.95 (13) | C12B—C11B—C10B | 122.99 (13) |
C19A—C10A—C11A | 118.33 (13) | C18B—C11B—C10B | 108.99 (12) |
C9A—C10A—C11A | 103.85 (13) | C12B—C11B—C7B | 113.15 (12) |
C19A—C10A—H10A | 105.5 | C18B—C11B—C7B | 106.36 (12) |
C9A—C10A—H10A | 105.5 | C10B—C11B—C7B | 102.87 (11) |
C11A—C10A—H10A | 105.5 | C13B—C12B—C17B | 119.13 (15) |
C12A—C11A—C18A | 101.70 (13) | C13B—C12B—C11B | 131.46 (15) |
C12A—C11A—C10A | 121.02 (13) | C17B—C12B—C11B | 109.39 (14) |
C18A—C11A—C10A | 109.68 (13) | C12B—C13B—C14B | 119.50 (18) |
C12A—C11A—C7A | 114.18 (13) | C12B—C13B—H13B | 120.3 |
C18A—C11A—C7A | 108.42 (13) | C14B—C13B—H13B | 120.3 |
C10A—C11A—C7A | 101.55 (12) | C15B—C14B—C13B | 120.41 (19) |
C13A—C12A—C17A | 119.06 (16) | C15B—C14B—H14B | 119.8 |
C13A—C12A—C11A | 131.61 (16) | C13B—C14B—H14B | 119.8 |
C17A—C12A—C11A | 109.32 (15) | C14B—C15B—C16B | 121.30 (18) |
C12A—C13A—C14A | 119.28 (19) | C14B—C15B—H15B | 119.4 |
C12A—C13A—H13A | 120.4 | C16B—C15B—H15B | 119.3 |
C14A—C13A—H13A | 120.4 | C15B—C16B—C17B | 118.00 (18) |
C15A—C14A—C13A | 120.7 (2) | C15B—C16B—H16B | 121.0 |
C15A—C14A—H14A | 119.6 | C17B—C16B—H16B | 121.0 |
C13A—C14A—H14A | 119.6 | C16B—C17B—C12B | 121.65 (17) |
C14A—C15A—C16A | 121.42 (19) | C16B—C17B—N2B | 128.47 (17) |
C14A—C15A—H15A | 119.3 | C12B—C17B—N2B | 109.83 (14) |
C16A—C15A—H15A | 119.3 | O3B—C18B—N2B | 126.06 (15) |
C15A—C16A—C17A | 117.7 (2) | O3B—C18B—C11B | 125.69 (15) |
C15A—C16A—H16A | 121.1 | N2B—C18B—C11B | 108.25 (13) |
C17A—C16A—H16A | 121.1 | C24B—C19B—C20B | 117.99 (17) |
C16A—C17A—C12A | 121.77 (19) | C24B—C19B—C10B | 118.93 (16) |
C16A—C17A—N2A | 128.54 (18) | C20B—C19B—C10B | 123.03 (17) |
C12A—C17A—N2A | 109.58 (15) | C21B—C20B—C19B | 120.7 (2) |
O3A—C18A—N2A | 126.33 (17) | C21B—C20B—H20B | 119.7 |
O3A—C18A—C11A | 125.75 (17) | C19B—C20B—H20B | 119.7 |
N2A—C18A—C11A | 107.91 (15) | C22B—C21B—C20B | 120.6 (2) |
C20A—C19A—C24A | 117.74 (16) | C22B—C21B—H21B | 119.7 |
C20A—C19A—C10A | 123.55 (15) | C20B—C21B—H21B | 119.7 |
C24A—C19A—C10A | 118.62 (15) | C21B—C22B—C23B | 119.7 (2) |
C19A—C20A—C21A | 120.96 (17) | C21B—C22B—H22B | 120.2 |
C19A—C20A—H20A | 119.5 | C23B—C22B—H22B | 120.2 |
C21A—C20A—H20A | 119.5 | C22B—C23B—C24B | 120.2 (3) |
C22A—C21A—C20A | 120.33 (19) | C22B—C23B—H23B | 119.9 |
C22A—C21A—H21A | 119.8 | C24B—C23B—H23B | 119.9 |
C20A—C21A—H21A | 119.8 | C23B—C24B—C19B | 120.9 (2) |
C23A—C22A—C21A | 119.40 (19) | C23B—C24B—H24B | 119.6 |
C23A—C22A—H22A | 120.3 | C19B—C24B—H24B | 119.6 |
C21A—C22A—H22A | 120.3 | C26B—C25B—C30B | 118.13 (17) |
C22A—C23A—C24A | 120.56 (19) | C26B—C25B—C9B | 120.90 (16) |
C22A—C23A—H23A | 119.7 | C30B—C25B—C9B | 120.96 (15) |
C24A—C23A—H23A | 119.7 | C25B—C26B—C27B | 120.5 (2) |
C23A—C24A—C19A | 120.98 (18) | C25B—C26B—H26B | 119.7 |
C23A—C24A—H24A | 119.5 | C27B—C26B—H26B | 119.7 |
C19A—C24A—H24A | 119.5 | C28B—C27B—C26B | 120.08 (19) |
C26A—C25A—C30A | 118.58 (17) | C28B—C27B—H27B | 120.0 |
C26A—C25A—C9A | 120.10 (17) | C26B—C27B—H27B | 120.0 |
C30A—C25A—C9A | 121.32 (16) | C29B—C28B—C27B | 119.8 (2) |
C25A—C26A—C27A | 120.4 (2) | C29B—C28B—H28B | 120.1 |
C25A—C26A—H26A | 119.8 | C27B—C28B—H28B | 120.1 |
C27A—C26A—H26A | 119.8 | C28B—C29B—C30B | 120.8 (2) |
C28A—C27A—C26A | 120.4 (2) | C28B—C29B—H29B | 119.6 |
C28A—C27A—H27A | 119.8 | C30B—C29B—H29B | 119.6 |
C26A—C27A—H27A | 119.8 | C25B—C30B—C29B | 120.7 (2) |
C29A—C28A—C27A | 119.6 (2) | C25B—C30B—H30B | 119.6 |
C29A—C28A—H28A | 120.2 | C29B—C30B—H30B | 119.6 |
C27A—C28A—H28A | 120.2 | N1B—C31B—C32B | 113.30 (16) |
C28A—C29A—C30A | 120.6 (2) | N1B—C31B—H31C | 108.9 |
C28A—C29A—H29A | 119.7 | C32B—C31B—H31C | 108.9 |
C30A—C29A—H29A | 119.7 | N1B—C31B—H31D | 108.9 |
C25A—C30A—C29A | 120.5 (2) | C32B—C31B—H31D | 108.9 |
C25A—C30A—H30A | 119.8 | H31C—C31B—H31D | 107.7 |
C29A—C30A—H30A | 119.8 | C33B—C32B—C37B | 118.51 (19) |
N1A—C31A—C32A | 114.58 (16) | C33B—C32B—C31B | 122.05 (17) |
N1A—C31A—H31A | 108.6 | C37B—C32B—C31B | 119.44 (19) |
C32A—C31A—H31A | 108.6 | C34B—C33B—C32B | 120.6 (2) |
N1A—C31A—H31B | 108.6 | C34B—C33B—H33B | 119.7 |
C32A—C31A—H31B | 108.6 | C32B—C33B—H33B | 119.7 |
H31A—C31A—H31B | 107.6 | C35B—C34B—C33B | 120.3 (2) |
C33A—C32A—C37A | 118.19 (19) | C35B—C34B—H34B | 119.9 |
C33A—C32A—C31A | 122.14 (16) | C33B—C34B—H34B | 119.9 |
C37A—C32A—C31A | 119.55 (18) | C36B—C35B—C34B | 120.0 (2) |
C32A—C33A—C34A | 120.68 (19) | C36B—C35B—H35B | 120.0 |
C32A—C33A—H33A | 119.7 | C34B—C35B—H35B | 120.0 |
C34A—C33A—H33A | 119.7 | C35B—C36B—C37B | 119.9 (2) |
C35A—C34A—C33A | 120.4 (2) | C35B—C36B—H36B | 120.0 |
C35A—C34A—H34A | 119.8 | C37B—C36B—H36B | 120.0 |
C33A—C34A—H34A | 119.8 | C36B—C37B—C32B | 120.7 (2) |
C34A—C35A—C36A | 119.9 (2) | C36B—C37B—H37B | 119.6 |
C34A—C35A—H35A | 120.0 | C32B—C37B—H37B | 119.6 |
C36A—C35A—H35A | 120.0 | O4B—C38B—N2B | 118.9 (2) |
C35A—C36A—C37A | 120.1 (2) | O4B—C38B—C39B | 122.5 (2) |
C35A—C36A—H36A | 119.9 | N2B—C38B—C39B | 118.58 (18) |
C37A—C36A—H36A | 119.9 | C38B—C39B—H39D | 109.5 |
C36A—C37A—C32A | 120.7 (2) | C38B—C39B—H39E | 109.5 |
C36A—C37A—H37A | 119.7 | H39D—C39B—H39E | 109.5 |
C32A—C37A—H37A | 119.7 | C38B—C39B—H39F | 109.5 |
O4A—C38A—N2A | 118.8 (3) | H39D—C39B—H39F | 109.5 |
O4A—C38A—C39A | 123.8 (2) | H39E—C39B—H39F | 109.5 |
N2A—C38A—C39A | 117.5 (3) | C8B—N1B—C1B | 111.15 (15) |
C38A—C39A—H39A | 109.5 | C8B—N1B—C31B | 123.50 (17) |
C38A—C39A—H39B | 109.5 | C1B—N1B—C31B | 124.62 (17) |
H39A—C39A—H39B | 109.5 | C18B—N2B—C38B | 126.07 (16) |
C38A—C39A—H39C | 109.5 | C18B—N2B—C17B | 109.15 (13) |
H39A—C39A—H39C | 109.5 | C38B—N2B—C17B | 124.76 (15) |
H39B—C39A—H39C | 109.5 | C7B—O2B—C9B | 109.27 (12) |
C8A—N1A—C1A | 111.31 (14) | C41—C40—H40A | 109.5 |
C8A—N1A—C31A | 122.81 (17) | C41—C40—H40B | 109.5 |
C1A—N1A—C31A | 124.22 (16) | H40A—C40—H40B | 109.5 |
C18A—N2A—C38A | 126.30 (19) | C41—C40—H40C | 109.5 |
C18A—N2A—C17A | 109.28 (14) | H40A—C40—H40C | 109.5 |
C38A—N2A—C17A | 124.35 (19) | H40B—C40—H40C | 109.5 |
C7A—O2A—C9A | 107.61 (12) | N3—C41—C40 | 178.2 (12) |
C2B—C1B—C6B | 121.57 (19) | C411—C401—H40D | 109.5 |
C2B—C1B—N1B | 128.27 (18) | C411—C401—H40E | 109.5 |
C6B—C1B—N1B | 110.06 (15) | H40D—C401—H40E | 109.5 |
C3B—C2B—C1B | 117.80 (19) | C411—C401—H40F | 109.5 |
C3B—C2B—H2B | 121.1 | H40D—C401—H40F | 109.5 |
C1B—C2B—H2B | 121.1 | H40E—C401—H40F | 109.5 |
C4B—C3B—C2B | 121.62 (19) | N31—C411—C401 | 175 (3) |
C6A—C1A—C2A—C3A | 3.4 (3) | C6B—C1B—C2B—C3B | −1.6 (3) |
N1A—C1A—C2A—C3A | −172.3 (2) | N1B—C1B—C2B—C3B | 174.53 (18) |
C1A—C2A—C3A—C4A | −0.4 (4) | C1B—C2B—C3B—C4B | −1.0 (3) |
C2A—C3A—C4A—C5A | −1.9 (5) | C2B—C3B—C4B—C5B | 1.8 (3) |
C3A—C4A—C5A—C6A | 1.2 (4) | C3B—C4B—C5B—C6B | −0.1 (3) |
C4A—C5A—C6A—C1A | 1.7 (3) | C4B—C5B—C6B—C1B | −2.4 (3) |
C4A—C5A—C6A—C7A | 177.3 (2) | C4B—C5B—C6B—C7B | −176.96 (17) |
C2A—C1A—C6A—C5A | −4.1 (3) | C2B—C1B—C6B—C5B | 3.3 (3) |
N1A—C1A—C6A—C5A | 172.28 (18) | N1B—C1B—C6B—C5B | −173.44 (15) |
C2A—C1A—C6A—C7A | 179.33 (18) | C2B—C1B—C6B—C7B | 178.96 (16) |
N1A—C1A—C6A—C7A | −4.3 (2) | N1B—C1B—C6B—C7B | 2.23 (19) |
C5A—C6A—C7A—O2A | −50.2 (3) | C5B—C6B—C7B—O2B | 49.8 (2) |
C1A—C6A—C7A—O2A | 125.79 (16) | C1B—C6B—C7B—O2B | −125.18 (14) |
C5A—C6A—C7A—C8A | −167.4 (2) | C5B—C6B—C7B—C8B | 168.62 (17) |
C1A—C6A—C7A—C8A | 8.56 (18) | C1B—C6B—C7B—C8B | −6.39 (17) |
C5A—C6A—C7A—C11A | 71.5 (3) | C5B—C6B—C7B—C11B | −70.8 (2) |
C1A—C6A—C7A—C11A | −112.54 (17) | C1B—C6B—C7B—C11B | 114.15 (16) |
O2A—C7A—C8A—O1A | 50.2 (2) | O2B—C7B—C8B—O1B | −53.4 (2) |
C6A—C7A—C8A—O1A | 168.12 (17) | C6B—C7B—C8B—O1B | −171.25 (17) |
C11A—C7A—C8A—O1A | −66.0 (2) | C11B—C7B—C8B—O1B | 62.6 (2) |
O2A—C7A—C8A—N1A | −128.04 (14) | O2B—C7B—C8B—N1B | 126.40 (14) |
C6A—C7A—C8A—N1A | −10.14 (17) | C6B—C7B—C8B—N1B | 8.56 (17) |
C11A—C7A—C8A—N1A | 115.76 (15) | C11B—C7B—C8B—N1B | −117.59 (15) |
O2A—C9A—C10A—C19A | 170.70 (12) | O2B—C9B—C10B—C19B | −151.19 (13) |
C25A—C9A—C10A—C19A | −71.61 (18) | C25B—C9B—C10B—C19B | 90.69 (17) |
O2A—C9A—C10A—C11A | 38.35 (15) | O2B—C9B—C10B—C11B | −19.76 (15) |
C25A—C9A—C10A—C11A | 156.04 (13) | C25B—C9B—C10B—C11B | −137.89 (14) |
C19A—C10A—C11A—C12A | −22.5 (2) | C19B—C10B—C11B—C12B | −0.8 (2) |
C9A—C10A—C11A—C12A | 109.04 (16) | C9B—C10B—C11B—C12B | −129.78 (15) |
C19A—C10A—C11A—C18A | 95.30 (17) | C19B—C10B—C11B—C18B | −119.22 (15) |
C9A—C10A—C11A—C18A | −133.17 (14) | C9B—C10B—C11B—C18B | 111.78 (14) |
C19A—C10A—C11A—C7A | −150.15 (14) | C19B—C10B—C11B—C7B | 128.19 (15) |
C9A—C10A—C11A—C7A | −18.61 (15) | C9B—C10B—C11B—C7B | −0.81 (15) |
O2A—C7A—C11A—C12A | −139.34 (14) | O2B—C7B—C11B—C12B | 156.30 (13) |
C6A—C7A—C11A—C12A | 96.12 (17) | C6B—C7B—C11B—C12B | −80.24 (18) |
C8A—C7A—C11A—C12A | −20.23 (18) | C8B—C7B—C11B—C12B | 36.05 (17) |
O2A—C7A—C11A—C18A | 108.09 (14) | O2B—C7B—C11B—C18B | −93.05 (14) |
C6A—C7A—C11A—C18A | −16.44 (18) | C6B—C7B—C11B—C18B | 30.41 (18) |
C8A—C7A—C11A—C18A | −132.80 (14) | C8B—C7B—C11B—C18B | 146.71 (13) |
O2A—C7A—C11A—C10A | −7.39 (15) | O2B—C7B—C11B—C10B | 21.47 (15) |
C6A—C7A—C11A—C10A | −131.93 (14) | C6B—C7B—C11B—C10B | 144.93 (14) |
C8A—C7A—C11A—C10A | 111.71 (14) | C8B—C7B—C11B—C10B | −98.77 (14) |
C18A—C11A—C12A—C13A | −168.43 (18) | C18B—C11B—C12B—C13B | 170.33 (17) |
C10A—C11A—C12A—C13A | −46.7 (3) | C10B—C11B—C12B—C13B | 48.4 (3) |
C7A—C11A—C12A—C13A | 75.0 (2) | C7B—C11B—C12B—C13B | −76.1 (2) |
C18A—C11A—C12A—C17A | 12.18 (17) | C18B—C11B—C12B—C17B | −11.33 (16) |
C10A—C11A—C12A—C17A | 133.90 (16) | C10B—C11B—C12B—C17B | −133.26 (15) |
C7A—C11A—C12A—C17A | −104.35 (16) | C7B—C11B—C12B—C17B | 102.26 (15) |
C17A—C12A—C13A—C14A | 0.0 (3) | C17B—C12B—C13B—C14B | −0.9 (3) |
C11A—C12A—C13A—C14A | −179.37 (17) | C11B—C12B—C13B—C14B | 177.30 (17) |
C12A—C13A—C14A—C15A | 1.2 (3) | C12B—C13B—C14B—C15B | −0.2 (3) |
C13A—C14A—C15A—C16A | −1.2 (3) | C13B—C14B—C15B—C16B | 0.8 (3) |
C14A—C15A—C16A—C17A | −0.1 (3) | C14B—C15B—C16B—C17B | −0.3 (3) |
C15A—C16A—C17A—C12A | 1.3 (3) | C15B—C16B—C17B—C12B | −0.8 (3) |
C15A—C16A—C17A—N2A | −174.41 (19) | C15B—C16B—C17B—N2B | 176.13 (17) |
C13A—C12A—C17A—C16A | −1.2 (3) | C13B—C12B—C17B—C16B | 1.4 (3) |
C11A—C12A—C17A—C16A | 178.23 (16) | C11B—C12B—C17B—C16B | −177.18 (15) |
C13A—C12A—C17A—N2A | 175.18 (15) | C13B—C12B—C17B—N2B | −176.03 (15) |
C11A—C12A—C17A—N2A | −5.34 (19) | C11B—C12B—C17B—N2B | 5.40 (18) |
C12A—C11A—C18A—O3A | 166.16 (18) | C12B—C11B—C18B—O3B | −167.17 (16) |
C10A—C11A—C18A—O3A | 36.9 (2) | C10B—C11B—C18B—O3B | −36.0 (2) |
C7A—C11A—C18A—O3A | −73.2 (2) | C7B—C11B—C18B—O3B | 74.26 (19) |
C12A—C11A—C18A—N2A | −14.86 (17) | C12B—C11B—C18B—N2B | 13.48 (16) |
C10A—C11A—C18A—N2A | −144.13 (14) | C10B—C11B—C18B—N2B | 144.64 (13) |
C7A—C11A—C18A—N2A | 105.80 (15) | C7B—C11B—C18B—N2B | −105.08 (14) |
C9A—C10A—C19A—C20A | −36.2 (2) | C9B—C10B—C19B—C24B | −135.80 (16) |
C11A—C10A—C19A—C20A | 89.18 (19) | C11B—C10B—C19B—C24B | 99.90 (18) |
C9A—C10A—C19A—C24A | 140.47 (16) | C9B—C10B—C19B—C20B | 41.4 (2) |
C11A—C10A—C19A—C24A | −94.14 (18) | C11B—C10B—C19B—C20B | −82.9 (2) |
C24A—C19A—C20A—C21A | 1.8 (3) | C24B—C19B—C20B—C21B | −0.8 (3) |
C10A—C19A—C20A—C21A | 178.49 (16) | C10B—C19B—C20B—C21B | −178.00 (18) |
C19A—C20A—C21A—C22A | −1.8 (3) | C19B—C20B—C21B—C22B | 0.6 (3) |
C20A—C21A—C22A—C23A | 0.6 (3) | C20B—C21B—C22B—C23B | 0.2 (4) |
C21A—C22A—C23A—C24A | 0.5 (3) | C21B—C22B—C23B—C24B | −0.7 (4) |
C22A—C23A—C24A—C19A | −0.4 (3) | C22B—C23B—C24B—C19B | 0.5 (4) |
C20A—C19A—C24A—C23A | −0.7 (3) | C20B—C19B—C24B—C23B | 0.2 (3) |
C10A—C19A—C24A—C23A | −177.54 (17) | C10B—C19B—C24B—C23B | 177.60 (19) |
O2A—C9A—C25A—C26A | −120.18 (18) | O2B—C9B—C25B—C26B | 146.23 (16) |
C10A—C9A—C25A—C26A | 125.84 (18) | C10B—C9B—C25B—C26B | −96.97 (19) |
O2A—C9A—C25A—C30A | 58.9 (2) | O2B—C9B—C25B—C30B | −33.8 (2) |
C10A—C9A—C25A—C30A | −55.1 (2) | C10B—C9B—C25B—C30B | 83.0 (2) |
C30A—C25A—C26A—C27A | 0.6 (3) | C30B—C25B—C26B—C27B | 0.1 (3) |
C9A—C25A—C26A—C27A | 179.8 (2) | C9B—C25B—C26B—C27B | 179.99 (17) |
C25A—C26A—C27A—C28A | −0.9 (4) | C25B—C26B—C27B—C28B | 0.2 (3) |
C26A—C27A—C28A—C29A | 0.4 (4) | C26B—C27B—C28B—C29B | −0.1 (4) |
C27A—C28A—C29A—C30A | 0.3 (4) | C27B—C28B—C29B—C30B | −0.4 (4) |
C26A—C25A—C30A—C29A | 0.1 (3) | C26B—C25B—C30B—C29B | −0.5 (3) |
C9A—C25A—C30A—C29A | −179.06 (18) | C9B—C25B—C30B—C29B | 179.6 (2) |
C28A—C29A—C30A—C25A | −0.5 (3) | C28B—C29B—C30B—C25B | 0.7 (4) |
N1A—C31A—C32A—C33A | −21.3 (3) | N1B—C31B—C32B—C33B | 34.0 (3) |
N1A—C31A—C32A—C37A | 162.68 (18) | N1B—C31B—C32B—C37B | −146.8 (2) |
C37A—C32A—C33A—C34A | 1.1 (3) | C37B—C32B—C33B—C34B | −0.2 (3) |
C31A—C32A—C33A—C34A | −175.0 (2) | C31B—C32B—C33B—C34B | 179.0 (2) |
C32A—C33A—C34A—C35A | −0.4 (4) | C32B—C33B—C34B—C35B | −0.1 (3) |
C33A—C34A—C35A—C36A | −0.7 (4) | C33B—C34B—C35B—C36B | 0.0 (3) |
C34A—C35A—C36A—C37A | 1.0 (4) | C34B—C35B—C36B—C37B | 0.3 (3) |
C35A—C36A—C37A—C32A | −0.2 (4) | C35B—C36B—C37B—C32B | −0.6 (3) |
C33A—C32A—C37A—C36A | −0.8 (3) | C33B—C32B—C37B—C36B | 0.6 (3) |
C31A—C32A—C37A—C36A | 175.4 (2) | C31B—C32B—C37B—C36B | −178.6 (2) |
O1A—C8A—N1A—C1A | −169.93 (17) | O1B—C8B—N1B—C1B | 171.97 (18) |
C7A—C8A—N1A—C1A | 8.35 (19) | C7B—C8B—N1B—C1B | −7.84 (18) |
O1A—C8A—N1A—C31A | −4.1 (3) | O1B—C8B—N1B—C31B | 1.4 (3) |
C7A—C8A—N1A—C31A | 174.22 (15) | C7B—C8B—N1B—C31B | −178.45 (16) |
C2A—C1A—N1A—C8A | 173.3 (2) | C2B—C1B—N1B—C8B | −172.69 (18) |
C6A—C1A—N1A—C8A | −2.8 (2) | C6B—C1B—N1B—C8B | 3.8 (2) |
C2A—C1A—N1A—C31A | 7.7 (3) | C2B—C1B—N1B—C31B | −2.2 (3) |
C6A—C1A—N1A—C31A | −168.44 (17) | C6B—C1B—N1B—C31B | 174.24 (17) |
C32A—C31A—N1A—C8A | 109.3 (2) | C32B—C31B—N1B—C8B | −128.2 (2) |
C32A—C31A—N1A—C1A | −86.6 (2) | C32B—C31B—N1B—C1B | 62.4 (3) |
O3A—C18A—N2A—C38A | 14.7 (3) | O3B—C18B—N2B—C38B | −12.2 (3) |
C11A—C18A—N2A—C38A | −164.3 (2) | C11B—C18B—N2B—C38B | 167.18 (16) |
O3A—C18A—N2A—C17A | −168.39 (19) | O3B—C18B—N2B—C17B | 169.51 (16) |
C11A—C18A—N2A—C17A | 12.64 (19) | C11B—C18B—N2B—C17B | −11.14 (17) |
O4A—C38A—N2A—C18A | 162.4 (2) | O4B—C38B—N2B—C18B | −171.1 (2) |
C39A—C38A—N2A—C18A | −16.8 (4) | C39B—C38B—N2B—C18B | 8.2 (3) |
O4A—C38A—N2A—C17A | −14.2 (4) | O4B—C38B—N2B—C17B | 6.9 (3) |
C39A—C38A—N2A—C17A | 166.7 (3) | C39B—C38B—N2B—C17B | −173.77 (19) |
C16A—C17A—N2A—C18A | 171.40 (19) | C16B—C17B—N2B—C18B | −173.46 (17) |
C12A—C17A—N2A—C18A | −4.7 (2) | C12B—C17B—N2B—C18B | 3.74 (18) |
C16A—C17A—N2A—C38A | −11.6 (3) | C16B—C17B—N2B—C38B | 8.2 (3) |
C12A—C17A—N2A—C38A | 172.3 (2) | C12B—C17B—N2B—C38B | −174.61 (16) |
C6A—C7A—O2A—C9A | 161.66 (14) | C6B—C7B—O2B—C9B | −164.71 (13) |
C8A—C7A—O2A—C9A | −86.38 (15) | C8B—C7B—O2B—C9B | 82.68 (16) |
C11A—C7A—O2A—C9A | 33.05 (16) | C11B—C7B—O2B—C9B | −36.38 (15) |
C25A—C9A—O2A—C7A | −167.77 (13) | C25B—C9B—O2B—C7B | 158.62 (13) |
C10A—C9A—O2A—C7A | −45.49 (15) | C10B—C9B—O2B—C7B | 36.10 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5A—H5A···O3A | 0.93 | 2.52 | 2.974 (3) | 111 |
C5B—H5B···O3B | 0.93 | 2.50 | 3.086 (2) | 121 |
C9A—H9A···O1A | 0.98 | 2.52 | 3.122 (2) | 119 |
C9B—H9B···O1B | 0.98 | 2.60 | 3.107 (2) | 113 |
C10A—H10A···O3A | 0.98 | 2.38 | 2.900 (2) | 113 |
C10B—H10B···O3B | 0.98 | 2.38 | 2.8883 (19) | 111 |
C13A—H13A···O1A | 0.93 | 2.52 | 2.911 (2) | 106 |
C13B—H13B···O1B | 0.93 | 2.53 | 3.033 (2) | 114 |
C16A—H16A···O4A | 0.93 | 2.34 | 2.856 (3) | 115 |
C16B—H16B···O4B | 0.93 | 2.29 | 2.830 (3) | 117 |
C27B—H27B···O1Bi | 0.93 | 2.46 | 3.308 (3) | 151 |
C31A—H31A···O1A | 0.97 | 2.50 | 2.872 (3) | 103 |
C31B—H31D···O1B | 0.97 | 2.51 | 2.896 (3) | 103 |
C34A—H34A···O4Aii | 0.93 | 2.50 | 3.387 (4) | 159 |
C3B—H3B···Cg1(C19A–C24A)iii | 0.93 | 2.99 | 3.472 (2) | 114 |
C24B—H24B···Cg2(C32A–C37A)iv | 0.93 | 2.83 | 3.637 (2) | 146 |
C39A—H39C···Cg2(C32A–C37A)iv | 0.96 | 2.84 | 3.690 (4) | 148 |
C33A—H33A···Cg3(C12A–C17A) | 0.93 | 2.75 | 3.578 (2) | 149 |
C33B—H33B···Cg4(C12B–C17B) | 0.93 | 2.77 | 3.680 (3) | 165 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+2, −y+2, −z+1; (iii) x, y, z+1; (iv) x−1, y, z. |
Experimental details
(I) | (II) | (III) | (IV) | |
Crystal data | ||||
Chemical formula | C44H33ClN2O3 | C39H29ClN2O4 | C39H30N2O4 | C39H30N2O4·0.5C2H3N |
Mr | 673.17 | 625.09 | 590.65 | 611.18 |
Crystal system, space group | Triclinic, P1 | Triclinic, P1 | Triclinic, P1 | Triclinic, P1 |
Temperature (K) | 294 | 294 | 294 | 294 |
a, b, c (Å) | 10.1099 (10), 11.3367 (11), 17.0315 (17) | 11.9830 (5), 12.9260 (6), 21.5664 (10) | 9.7565 (10), 16.6868 (16), 19.9593 (19) | 9.6940 (5), 18.581 (1), 20.1552 (11) |
α, β, γ (°) | 74.755 (2), 78.503 (2), 65.557 (2) | 76.330 (1), 76.522 (1), 77.553 (1) | 71.653 (2), 81.657 (2), 89.314 (2) | 114.872 (2), 98.465 (2), 99.397 (2) |
V (Å3) | 1705.4 (3) | 3110.6 (2) | 3049.7 (5) | 3153.6 (3) |
Z | 2 | 4 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.16 | 0.17 | 0.08 | 0.08 |
Crystal size (mm) | 0.15 × 0.08 × 0.06 | 0.13 × 0.11 × 0.06 | 0.11 × 0.08 × 0.06 | 0.18 × 0.08 × 0.07 |
Data collection | ||||
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer | Bruker SMART APEX CCD area-detector diffractometer | Bruker SMART APEX CCD area-detector diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) | Multi-scan (SADABS; Bruker, 2001) | Multi-scan (SADABS; Bruker, 2001) | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.92, 0.98 | 0.94, 0.97 | 0.96, 0.99 | 0.97, 0.99 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20091, 8008, 6578 | 36879, 14644, 8962 | 29800, 10763, 6882 | 37306, 14817, 10357 |
Rint | 0.020 | 0.034 | 0.036 | 0.023 |
(sin θ/λ)max (Å−1) | 0.667 | 0.668 | 0.595 | 0.668 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.066, 0.155, 1.13 | 0.068, 0.160, 1.04 | 0.070, 0.149, 1.09 | 0.058, 0.147, 1.01 |
No. of reflections | 8008 | 14644 | 10763 | 14817 |
No. of parameters | 451 | 831 | 813 | 870 |
No. of restraints | 0 | 0 | 0 | 70 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.32, −0.17 | 0.27, −0.19 | 0.22, −0.17 | 0.27, −0.16 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXS97 (Sheldrick, 2015), SHELXL2014 (Sheldrick, 2015), DIAMOND (Brandenburg & Putz, 2005) and Mercury (Macrae et al., 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O3 | 0.93 | 2.55 | 3.067 (2) | 116 |
C9—H9···O1 | 0.98 | 2.60 | 3.115 (2) | 113 |
C10—H10···O3 | 0.98 | 2.45 | 2.951 (2) | 111 |
C13—H13···O1 | 0.93 | 2.40 | 3.011 (3) | 123 |
C31—H31B···O1 | 0.97 | 2.53 | 2.914 (3) | 104 |
C38—H38A···O3 | 0.97 | 2.51 | 2.881 (3) | 103 |
C31—H31A···O2i | 0.97 | 2.61 | 3.417 (2) | 141 |
C3—H3···Cg1(C32–C37)ii | 0.93 | 2.90 | 3.734 (2) | 149 |
C27—H27···Cg2(C1–C6)iii | 0.93 | 2.91 | 3.537 (2) | 126 |
C33—H33···Cg3(C12–C17) | 0.93 | 2.90 | 3.560 (2) | 147 |
Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x+1, −y+2, −z+1; (iii) x+1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C5A—H5A···O3A | 0.93 | 2.57 | 3.157 (3) | 122 |
C5B—H5B···O3B | 0.93 | 2.56 | 3.118 (4) | 119 |
C9A—H9A···O1A | 0.98 | 2.69 | 3.152 (3) | 109 |
C9B—H9B···O1B | 0.98 | 2.53 | 3.088 (3) | 116 |
C10A—H10A···O3A | 0.98 | 2.39 | 2.881 (3) | 111 |
C10B—H10B···O3B | 0.98 | 2.34 | 2.871 (3) | 113 |
C13A—H13A···O1A | 0.93 | 2.64 | 3.157 (3) | 115 |
C13B—H13B···O1B | 0.93 | 2.49 | 3.003 (3) | 115 |
C16A—H16A···O4A | 0.93 | 2.30 | 2.840 (4) | 117 |
C16B—H16B···O4B | 0.93 | 2.29 | 2.835 (5) | 117 |
C20A—H20A···O1A | 0.93 | 2.43 | 3.256 (3) | 148 |
C20B—H20B···O1B | 0.93 | 2.70 | 3.515 (3) | 147 |
C27B—H27B···O1Ai | 0.93 | 2.59 | 3.374 (3) | 142 |
C30A—H30A···O3A | 0.93 | 2.47 | 3.314 (3) | 151 |
C30B—H30B···O3B | 0.93 | 2.85 | 3.701 (3) | 153 |
C31A—H31A···O1A | 0.97 | 2.53 | 2.913 (3) | 104 |
C31B—H31D···O1B | 0.97 | 2.55 | 2.921 (3) | 104 |
C15A—H15A···Cg3(C19B–C24B) | 0.93 | 2.91 | 3.808 (14) | 163 |
C33A—H33A···Cg4(C12A–C17A) | 0.93 | 2.89 | 3.717 (3) | 149 |
C33B—H33B···Cg5(C12B–C17B) | 0.93 | 2.64 | 3.485 (3) | 151 |
Symmetry code: (i) x−1, y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C5A—H5A···O3A | 0.93 | 2.53 | 3.109 (4) | 121 |
C5B—H5B···O3B | 0.93 | 2.53 | 2.973 (4) | 109 |
C9A—H9A···O1A | 0.98 | 2.61 | 3.115 (3) | 112 |
C9B—H9B···O1B | 0.98 | 2.53 | 3.125 (3) | 119 |
C10A—H10A···O3A | 0.98 | 2.38 | 2.876 (3) | 111 |
C10B—H10B···O3B | 0.98 | 2.39 | 2.910 (3) | 113 |
C13A—H13A···O1A | 0.93 | 2.53 | 3.057 (4) | 116 |
C13B—H13B···O1B | 0.93 | 2.42 | 2.880 (4) | 110 |
C16A—H16A···O4A | 0.93 | 2.31 | 2.853 (6) | 116 |
C16B—H16B···O4B | 0.93 | 2.27 | 2.813 (5) | 117 |
C27A—H27A···O1Ai | 0.93 | 2.46 | 3.310 (4) | 152 |
C31A—H31A···O1A | 0.97 | 2.51 | 2.892 (4) | 103 |
C31B—H31D···O1B | 0.97 | 2.49 | 2.866 (4) | 103 |
C3A—H3A···Cg1(C19B–C24B)ii | 0.93 | 2.98 | 3.474 (4) | 115 |
C24A—H24A···Cg2(C32B–C37B)iii | 0.93 | 2.86 | 3.677 (3) | 147 |
C31B—H31C···Cg3(C25A–C30A)iv | 0.97 | 2.96 | 3.889 (4) | 161 |
C33A—H33A···Cg4(C12A–C17A) | 0.93 | 2.72 | 3.602 (4) | 158 |
C33B—H33B···Cg5(C12B–C17B) | 0.93 | 2.80 | 3.572 (4) | 142 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x+1, y+1, z; (iii) x, y, z+1; (iv) x, y, z−1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C5A—H5A···O3A | 0.93 | 2.52 | 2.974 (3) | 111 |
C5B—H5B···O3B | 0.93 | 2.50 | 3.086 (2) | 121 |
C9A—H9A···O1A | 0.98 | 2.52 | 3.122 (2) | 119 |
C9B—H9B···O1B | 0.98 | 2.60 | 3.107 (2) | 113 |
C10A—H10A···O3A | 0.98 | 2.38 | 2.900 (2) | 113 |
C10B—H10B···O3B | 0.98 | 2.38 | 2.8883 (19) | 111 |
C13A—H13A···O1A | 0.93 | 2.52 | 2.911 (2) | 106 |
C13B—H13B···O1B | 0.93 | 2.53 | 3.033 (2) | 114 |
C16A—H16A···O4A | 0.93 | 2.34 | 2.856 (3) | 115 |
C16B—H16B···O4B | 0.93 | 2.29 | 2.830 (3) | 117 |
C27B—H27B···O1Bi | 0.93 | 2.46 | 3.308 (3) | 151 |
C31A—H31A···O1A | 0.97 | 2.50 | 2.872 (3) | 103 |
C31B—H31D···O1B | 0.97 | 2.51 | 2.896 (3) | 103 |
C34A—H34A···O4Aii | 0.93 | 2.50 | 3.387 (4) | 159 |
C3B—H3B···Cg1(C19A–C24A)iii | 0.93 | 2.99 | 3.472 (2) | 114 |
C24B—H24B···Cg2(C32A–C37A)iv | 0.93 | 2.83 | 3.637 (2) | 146 |
C39A—H39C···Cg2(C32A–C37A)iv | 0.96 | 2.84 | 3.690 (4) | 148 |
C33A—H33A···Cg3(C12A–C17A) | 0.93 | 2.75 | 3.578 (2) | 149 |
C33B—H33B···Cg4(C12B–C17B) | 0.93 | 2.77 | 3.680 (3) | 165 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+2, −y+2, −z+1; (iii) x, y, z+1; (iv) x−1, y, z. |
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