research papers
in double-pillared-layer coordination polymers – structures and photoreactivity
aDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore, and bDepartment of Chemistry and Research Institute of Natural Science, Gyeongsang National University, Jinju, 52828, Republic of Korea
*Correspondence e-mail: sslee@gnu.ac.kr, chmjjv@nus.edu.sg
The existence of trans,cis,trans-bpeb ligands with conjugated olefin bonds are aligned in close proximity in both of the structures, one isomer undergoes a double [2 + 2] cycloaddition reaction and the second isomer only offers an incomplete single cycloaddition product. This work demonstrates how small changes in the structural connectivity can have an impact on the overall structural, physical and chemical properties of such materials.
in coordination polymeric structures offers opportunities to understand structure–function relationships. Herein the serendipitous isolation is reported of two isomeric double-pillared-layer coordination polymeric structures arising from two different types of carboxylate bonding of benzene-1,4-dicarboxylate ligands to zinc(II), which constitutes a new type of structural The different bonding modes not only alter the shape and size of the pores, but also the nature of interpenetration and photoreactivity. Although two1. Introduction
Recent advances in the design and construction of a wide variety of highly crystalline coordination polymers (CPs) and metal–organic frameworks (MOFs) are mainly based on the self-assembly of these compounds in a one-pot crystallization process (Steed & Atwood, 2009; Ramanan & Whittingham, 2006). Researchers seek to engineer, fine tune and control the chemical composition, dimensionality, connectivity, topology, interpenetration, pore size and shape of these solid-state materials in order to vary their physical and chemical properties for various applications (Kitagawa et al., 2004; Horike et al., 2009; Long & Yaghi, 2009; Zhou et al., 2012; Janiak, 2003; Moulton & Zaworotko, 2001; Zaworotko, 2001; Zhang et al., 2008). In other words, the solid-state properties are dictated by the molecular packing, which in turn is influenced by crystallization conditions. The crystallization conditions may yield not only different polymorphs but also isomeric products. In the multi-dimensional coordination polymeric structures, various types of structural and are possible that are similar to those encountered in discrete molecules, in addition to supramolecular (Moulton & Zaworotko, 2001; Zaworotko, 2001; Zhang et al., 2008; Guillerm et al., 2014). These isomers provide opportunities to improve our understanding of the structure–function relationship in these polymeric materials. In this respect, new types of in CPs and MOFs have been discovered to yield interesting solid properties (Blake, 2001; Barnett et al., 2012; Hu et al., 2012; Panda et al., 2013; Poplaukhin & Tiekink, 2010; Manna et al., 2008; Karmakar et al., 2017).
Carboxylates are known to have a variety of bonding modes to the metal centres (Guo et al., 2013). Dicarboxylate spacer ligands such as the 1,4-benzenedicarboxylate anion can connect metal ions in three different ways using their chelating and bridging abilities, as shown in Fig. 1(a). These three types of bonding modes can generate two structural isomers while maintaining the same (4,4) connectivity as shown in Figs. 1(b) and 1(c) (Gong et al., 2013; Park et al., 2017). It may be noted that the isomer containing both type-I and type-II dicarboxylate linkages in the [M2(dicarboxylate)2] layer (Fig. 1b) has an ideal rectangular shape with mm symmetry. The second isomer with type-III linkages has the shape of an ideal square with fourfold rotational symmetry in the [M2(dicarboxylate)2] building block, as displayed in Fig. 1(c).
Synthesis and isolation of these two closely related structural isomers are challenging. Furthermore, they are expected to form concomitantly in one synthesis. These two types of connectivities have been reported recently for dicarboxylates with different chemical compositions (Gong et al., 2013; Park et al., 2017). To the best of our knowledge, such structural has not yet been documented in metal complexes or CPs with the same chemical formula.
The influence of the single- and double-pillared-layer structures on the physical properties and chemical reactivities has been investigated (Takashima et al., 2011; Mahata et al., 2006; Kitaura et al., 2002, 2003; Kitagawa & Matsuda, 2007; Sato et al., 2010; Park, Medishetty et al., 2014; Park et al., 2015; Chun et al., 2005; Seo et al., 2009; Maji et al., 2004; Henke et al., 2012). Supramolecular isomers with different dimensionalities and topologies have been shown to possess different physical properties (Moulton & Zaworotko, 2001; Zaworotko, 2001). Since the two structural isomers described here have the same topology and differ only in their dicarboxylate bonding modes, it is interesting to investigate their properties. During our attempts to grow higher quality single crystals suitable for data collection, we isolated a double-pillared-layer coordination polymeric structure with the {Zn2(bpeb)2(bdc)2] {bdc = 1,4-benzenedicarboxylate, bpeb = 1,4-bis[2-(4-pyridyl)ethenyl]benzene}, when dimethylformamide (DMF) was used as one of the solvents. When DMF was replaced by dimethylacetamide (DMA), we were able to isolate two structural isomers formed concomitantly in a one-pot synthesis as major and minor products. Of these two isomers exhibiting twofold interpenetration, one has parallel and the other has perpendicular interpenetration with respect to the bpeb pillar ligands. As these pillar ligands have olefin bonds arranged in close proximity, it gives an opportunity to investigate the [2 + 2] photoreactivity in these two supramolecular isomers. Further photoluminescent properties were also recorded and discussed in this report.
2. Results and discussion
The single crystals of [Zn2(bpeb)2(bdc)2]·2DMF·2H2O·0.5DMSO (1) were obtained from Zn(NO3)2·6H2O, H2bdc and bpeb in a 1:1:1 molar ratio in a mixture of DMF, dimethyl sulfoxide (DMSO) and water along with a few drops of NaOH solution heated at 393 K for 48 h. When DMF was replaced by DMA, a similar solvothermal synthesis yielded the supramolecular isomers of [Zn2(bpeb)2(bdc)2]·2DMA·2H2O (2) and [Zn2(bpeb)2(bdc)2]·DMA (3) concomitantly. Plate-like yellow crystals of (2) were the major product, whereas pale-yellow rod-shaped crystals of (3) were the minor product (less than 1%) in this reaction. We were unable to obtain (3) in larger quantities by changing the experimental conditions. The solid-state structures determined from single-crystal X-ray diffraction techniques are described below.
The 1), which crystallized in P21/c with Z = 4, has a formula unit in which both bpeb ligands are disordered, see Fig. 2(a). Interestingly, each bpeb ligand has both trans,trans,trans (all-trans) and trans,cis,trans conformations in the ratio of 60:40, respectively. The dinuclear repeating unit consists of two ZnII atoms bridged by two carboxylate groups; each ZnII is chelated by a carboxylate group (Fig. 2b). The bridging carboxylates have a syn-anti-μ2-η1:η1 bonding mode observed from the two sets of Zn—O—C angles [128.9 (3)° and 128.4 (3)°; 150.2 (3)° and 148.1 (3)°]. The [Zn2(O2C—C)2] is roughly planar. The exo-carboxylate groups in the para positions of the bdc ligands are connected to generate a (4,4) layer structure of [Zn2(bdc)2]. In fact, the Zn—bpeb—Zn distance and the diagonal distances between the centres of the Zn2 dimer in the Zn2(bdc)2 rhomboidal ring are the a, b and c unit-cell lengths. Furthermore, a closer examination reveals that each bdc has type-III carboxylate bonding. The (4,4) grid is rhombus-shaped as a result of the symmetrical bonding, with the dimensions 12.530 × 12.554 Å and an angle of 79°. The axial positions of the highly distorted octahedral ZnII centres are occupied by the nitrogen atoms of the bpeb ligands. The bpeb ligands are acting like pillars, connecting the [Zn2(bdc)2] layers through pyridyl groups to produce double-pillared-layer structures with primitive cubic unit (pcu) topology (Fig. 2c). The structure is doubly interpenetrated as a result of the large empty space. It may be noted that a pair of bpeb pillars from the neighbouring pcu unit penetrate each rhomboidal ring in the [Zn2(bdc)2] layer, thus forming a twofold parallel interpenetration as displayed in Fig. 2(c). The empty cavity generated by the bpeb ligands is filled by the double interpenetration. The total potential solvent area volume in (1), calculated using PLATON (Spek, 2009), is 1633 Å3, which is 26.8% of the unit-cell volume 6094.6 Å3.
of (Compound (2) was the major product of the crystallization using DMA in the solvothermal reaction and crystallized in the orthorhombic Pcca (No. 54) with Z = 4 (Fig. S2 in the supporting information). The has half of the formula unit, i.e. [Zn(bpeb)(bdc)]. In this structure, the middle ring (C8–C15) of the bpeb is disordered and hence a mixture of all-trans and trans,cis,trans conformations are present (Fig. S2a). Otherwise, the structural description is very similar to that of (1) with type-III bonding of the bdc ligand as well as twofold parallel interpenetration (Fig. S2d). However, the Zn—bpeb—Zn distance and the diagonal distances between the centres of the Zn2 dimer in the Zn2(bdc)2 rhomboidal ring are the b, a and c unit-cell lengths. The total potential solvent area volume in (2), calculated using PLATON (Spek, 2009), is 1912 Å3, which is 30.6% of the unit-cell volume 6247.5 Å3.
The minor product (3) crystallized in the monoclinic C2/c with Z = 8 (Fig. 3). The contains the building unit [Zn2(bpeb)2(bdc)2]. In this `no disorder' structure, both bpeb have trans,cis,trans conformations (Fig. 3b). Furthermore, two types of bdc bonding, namely type-I and type-II, are present in the [Zn2(bdc)2] layer (Fig. 3a), resulting in a parallelogram-shaped (4,4) grid with the dimensions 14.948 × 10.159 Å and an angle of 77.1°. The overall connectivity has pcu topology (Fig. 3c) similar to (1) and (2). This also has twofold interpenetration, but the [Zn2(bpeb)2(bdc)2] units are normal with respect to each other as shown in Fig. 3(c). This could be attributed to insufficient space for the two bpeb pillars to interpenetrate the (4,4) net. On the other hand, the void formed by Zn—bpeb—Zn and Zn-(type-II) bdc—Zn with the dimensions 20.127 × 14.948 Å is sufficient to form a twofold perpendicular interpenetration. The total potential solvent area volume in (3), calculated using PLATON (Spek, 2009), is 2769.2 Å3, which is 24.3% of the unit-cell volume 11 388.7 Å3, indicating that this structure is more efficiently packed than (2).
In the double-pillared-layer structures, the two ZnII centres assist in bringing the axial bpeb pillar ligands closer such that the olefin pairs satisfy Schmidt's conditions for a [2 + 2] photocycloaddition reaction (Schmidt, 1971). Interestingly, the two disordered bpeb ligands in (1) adopt a mixture of all-trans and trans,cis,trans-conformation (Fig. 2b). Nonetheless, the six-membered rings in the two bpeb ligands are aligned in a face-to-face manner with a separation in the range 3.572–4.150 Å. The centres of the two olefin pairs are also separated by a distance in the range 3.854–4.006 Å, which is congenial for double [2 + 2] cycloaddition reactions. However, because of the presence of mixed conformations in the disordered ligands, it was difficult to predict a priori the outcome of the photoreaction under UV light.
The 1H NMR spectrum of solid (1) was collected after irradiation under UV light for 48 h and dissolution in DMSO-d6 aided by a drop of HNO3; it showed the appearance of cyclobutane peaks at 4.9–4.6 and 5.3–5.20 p.p.m. along with other peaks attributed to the aromatic protons in the region 7.7–8.9 p.p.m. (Fig. S14). Although 1H NMR data indicated double dimerization, the nature of the product was not clear. To investigate the solid-state structure of the photo-irradiated product of (1), named (4), we attempted to obtain single crystals of product (4) at the end of the cycloaddition reaction and eventually succeeded.
The single-crystal X-ray crystallographic analysis of [Zn2(tppcp)(bdc)2] (4) [tppcp = tetrakis(4-pyridyl)-1,2,9,10-diethano[2.2]paracyclophane, Fig. 4a)] proved the quantitative photo cycloaddition of the trans,cis,trans-bpeb pairs (Fig. 4b). Obviously the partially disordered all-trans conformation had changed to the trans,cis,trans conformation under UV light. Interestingly the changed to Pcca with Z = 4 and the contained half of the unit-cell formula. The double [2 + 2] cycloaddition product tppcp is disordered due to the presence of a centre of inversion at the centre of the ligand structure. Furthermore, the Zn—(tppcp)—Zn distance and diagonal distances between the centres of the Zn2 dimer in the Zn2(bdc)2 rhomboidal ring are the b, a and c unit-cell lengths. Therefore, the packing is very similar to that of (2).
In (2), both the bpeb pairs have a disordered mixture of all-trans and trans,cis,trans conformations similar to (1). The olefin bonds in these bpeb pairs were separated by 3.544 and 3.728 Å, hence (2) is also expected to be photoreactive. The photoreactivity of (2) was investigated under UV light. Solid (2) was irradiated under UV light for 48 h; the irradiated product (5) was dissolved in DMSO-d6 aided by of a drop of HNO3 to obtain an 1H NMR spectrum, which showed the appearance of cyclobutane peaks at 4.6–4.9 p.p.m. along with other peaks attributed to aromatic protons in the region 7.7–8.9 p.p.m. (Fig. S15). In order to gain more insight into the nature of the photoproduct, we attempted a single-crystal-to-single-crystal (SCSC) reaction under UV light and succeeded.
As proven by single-crystal X-ray crystallography, the Pcca) of the photoproduct [Zn2(tppcp)(bdc)2] (5) was retained from (2). Although the quality of the structure was poor, it was found to be isotypical to that of (4). The quantitative photocycloaddition of the trans,cis,trans-bpeb pairs was observed. It is interesting to find that both (1) and (2) crystallized in two different space groups, yet gave isotypical photoproducts (4) and (5). It is noted that the double dimerization in bpeb has been reported in both organic compounds and MOFs, but arising only from all-trans-bpeb pairs (Papaefstathiou et al., 2005; Friščič & MacGillivray, 2003; Liu et al., 2010).
(Finally, the solid-state photoreactivity of (3) was examined under UV light. The bpeb pairs have trans,cis,trans conformation, arranged in an approximately face-to-face manner with an interplanar angle of 11.4°. This was also expected to be photoreactive as the olefin bonds in these bpeb pairs were separated by 3.938 and 3.927 Å. Solid (3) was irradiated under UV light for 48 h and the irradiated product (6) was treated under similar conditons to (1) in order to obtain an 1H NMR spectrum. It showed the appearance of cyclobutane peaks at 5.08 and 4.86 p.p.m. along with other peaks attributed to aromatic protons in the region 7.7–8.9 p.p.m. (Fig. S16). There were a number of unreacted olefin groups indicated by the presence of peaks at 7.62 and 8.00 p.p.m.. It appears that (3) undergoes an incomplete [2 + 2] cycloaddition reaction.
In order to gain more insight into the nature of the above photoproduct, we attempted an SCSC reaction under UV light. and we were able to get single crystals of the partially photodimerized product. X-ray crystallographic analysis of (6) shows that the cyclobutane ring was formed between one of the two bpeb pairs, as shown in Fig. 5. Furthermore, only partial dimerization (38.9%) occurred in this crystal. Prolonged UV irradiation only destroyed the single crystals. We were unable to confirm whether complete dimerization of the single olefin pairs is possible in (3), resulting from a lack of suitable single crystals and the scarcity of the compound. Such photodimerization of single olefin pairs in bpeb has been reported before (Friščić & MacGillivray, 2006). It is evident that the photoreactive behaviour of (3) is completely different from that of (1) and (2). The packing in (3) is more efficient than in (2), as shown by the respective void volumes [30.6% in (2) versus 24.3% in (3). This indicates that the bpeb pairs in (3) do not have enough free volume to undergo double dimerization as in (1) or (2) and provides an explanation for the inability of (3) to remian as a single crystal after quantitative single dimerization. This is also supported by non-parallel orientations of the central phenylene rings (interplanar angle, 29.9°) of the bpeb pairs in (3).
3. Conclusions
In summary, we have serendipitously isolated two structural isomers as a result of the different bonding modes of carboxylates in the bdc ligands present in the double-pillared-layer coordination polymers. We were able to synthesize one of the isomers (1) exclusively, but only a small quantity of the second isomer (3). These isomers are expected to have similar energies and are likely to be kinetic products. The MOF with diamondoid topology reported previously is also a supramolecular isomer to (1)-(3), this could be considered as the thermodynamic product (Park, Chanthapally et al., 2014; Park et al. 2016). We have not found suitable experimental conditions to synthesize (3) exclusively despite many attempts. The isolation of energetically similar isomers can be compared with discovering new polymorphs of organic crystals (Haleblian & McCrone, 1969; Bernstein, 2002). These new types of structural isomers have a different packing efficiency, nature of interpenetration and photoreactivity. The two pillared trans,cis,trans-bpeb ligands with conjugated olefin bonds are closely aligned to each other in both structures. The isomers (1) and (2) can undergo face-to-face double [2 + 2] cycloaddition reactions and the isomer (3) yields only the partial single cycloaddition product, (6). These results highlight how small structural differences can influence the overall structural, physical and chemical properties. Perpendicular interpenetration observed in (3) seems to be more efficient for crystal packing, but this is not congenial for face-to-face double dimerization of the bpeb pairs. This work highlights the possibility of fine tuning the packing and photoreactivity of CPs and MOFs through structural isomerism.
4. Experimental
4.1. General
All the chemicals were reagent grade and were used without further purification. The bpeb ligand was synthesized by the reported procedure (Gutov et al., 2009). Elemental analyses were carried out using a LECO CHNS-932 elemental analyser. The infrared (IR) spectra (4000–400 cm-1) were recorded on a Thermo Fisher Scientific Nicolet iS 10 F T-IR spectrometer using KBr pellets. Thermogravimetric analyses (TGA) were performed under a nitrogen atmosphere with a heating rate of 5 K min−1 using a TA Instruments TGA-Q50 thermogravimetric analyser. For the TGA analysis, drying the product at 343 K for 24 h led to the loss of guest water molecules. The solid-state emission spectra were obtained from a Shimadzu RF-5301PC, using powder samples packed between glass slides in air at room temperature (296 K) using an excitation wavelength of 360 nm. Powder X-ray diffraction (PXRD) patterns were recorded on a D8 DISCOVER with GADDS (Bruker AXS) with graphite-monochromated Cu Kα radiation (λ = 1.54056 Å) at room temperature (296 K). The UV–vis spectra were recorded on a Shimadzu UV-3600 UV-VIS-NIR spectrometer. The UV irradiation experiments were carried out on a LUZCHEM UV reactor with an 8 W dark-blue phosphor lamp (300–400 nm).
4.2. Preparation of [Zn2(bpeb)2(bdc)2]·2DMF·2H2O·0.5DMSO (1)
A mixture of bpeb (20.2 mg, 0.071 mmol), H2bdc (12.0 mg, 0.072 mmol) and Zn(NO3)2·4H2O (18.6 mg, 0.071 mmol) dissolved in DMF (3 ml), H2O (1 ml) and DMSO (0.5 ml) were placed in a 10 ml glass tube, and then 3–4 drops of 0.1 M NaOH were added. The tube was sealed and kept at 393 K for 48 h, followed by cooling to room temperature (296 K) over 8 h. Pale-yellow block-shaped crystals of (1) suitable for X-ray analysis were obtained (yield 45%). Analysis, calculated for [C63H61N6O12.5S0.5Zn2]: C, 60.58; H, 4.92; N, 6.73; S, 1.28%; found: C, 60.45; H, 4.63; N, 6.66; S, 1.47%; IR (KBr pellet) 3447, 3051, 2926, 2838, 1676, 1605, 1501, 1429, 1385, 1257, 1220, 1132, 1092, 1067, 1017, 970, 875, 835, 750 and 659 cm−1.
4.3. Preparation of a mixture of [Zn2(bpeb)2(bdc)2]·2DMA ·2H2O (2) and [Zn2(bpeb)2(bdc)2]·DMA (3)
A mixture of bpeb (19.9 mg, 0.070 mmol), H2bdc (11.8 mg, 0.071 mmol) and Zn(NO3)2·4H2O (18.8 mg, 0.072 mmol) dissolved in DMA (3 ml), H2O (1 ml) and DMSO (0.5 ml) were placed in a 10 ml glass tube, and then 3–4 drops of 0.1 M NaOH were added. The tube was sealed and kept at 393 K for 48 h, followed by cooling to room temperature (296 K) over 8 h. Pale-yellow plate-shaped crystals (2) (major) and pale-yellow rod-shaped crystals (3) (as a minor product, less than ~1% yield) suitable for X-ray analysis were obtained. For (2): analysis, calculated for [C64H62N6O12Zn2]: C, 62.09; H, 5.05; N, 6.79%; found: C, 62.15; H, 5.02; N, 7.21%; IR (KBr pellet) 3026, 2884, 2821, 1637, 1609, 1508, 1388, 1224, 1036, 954, 869, 840, 752 and 664 cm−1. For (3): IR (KBr pellet) 3033, 2895, 1631, 1543, 1388, 1237, 1073, 949, 830, 751, 715 and 668 cm−1. (3) was produced only in very low yield, hence no analytical or IR data could be obtained for this compound.
4.4. Preparation of [Zn2(tppcp)(bdc)2]·1.6DMF·2.8H2O·0.2DMSO (4)
(4) was obtained by UV irradiation of the single crystals of (1) for 48 h. Analysis, calculated for [C61.2H58N5.6O12.6S0.2Zn2]: C, 60.71; H, 4.83; N, 6.48; S, 0.53%; found: C, 60.95; H, 4.72; N, 6.19; S, 0.49%; IR (KBr pellet) 3447, 3045, 2946, 2883, 1674, 1616, 1542, 1507, 1387, 1224, 1093, 1071, 830, 751 and 669 cm−1.
4.5. Preparation of [Zn2(tppcp)(bdc)2]·2DMA·2H2O (5) and [Zn2(bpeb)0.6(bpbpvpcb)0.4(bdc)2]·DMA (6)
(5) and (6) were obtained by UV irradiation of the single crystals of (2) and (3) for 48 h, respectively. For (5): analysis, calculated for [C62.8H61.5N5.7O12.8Zn2]: C, 61.24; H, 5.03; N, 6.48; found: C, 61.11; H, 4.79; N, 6.17%; IR (KBr pellet) 3447, 3044, 2943, 1618, 1501, 1388, 1224, 1071, 1016, 928, 829, 751, 706 and 669 cm−1. For (6): IR (KBr pellet) 3051, 2932, 1605, 1524, 1375, 1237, 1073, 949, 830, 751, 715 and 668 cm−1. (6) was produced only in very low yield, hence no analytical or IR data could be obtained for this compound.
4.6. X-ray crystallographic analysis
Crystal data for (1) were collected at 100 K and (2)-(6) were collected at 173 K on a Bruker SMART APEX II ULTRA diffractometer equipped with graphite-monochromated Mo Kα radiation (λ = 0.71073 Å) generated by a rotating anode (Table 1). The preliminary cell parameters for the compounds were obtained from a least-squares (from 36 collected frames). Data collection, data reduction and absorption correction were carried out using the software package of APEX2 (Bruker, 2008). All of the calculations for the were carried out using the SHELXTL package (Bruker, 2001). Relevant crystal data collection and data for the crystal structures of (1)–(6) are summarized in Table S1.
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5. Related literature
The following references are cited in the supporting information: Balamurugan et al. (2012); Elacqua et al. (2009); Spek (2015); Horner & Hünig (1982); Peedikakkal & Vittal (2008); Peedikakkal et al. (2010).
Supporting information
https://doi.org/10.1107/S2052252518001379/lc5095sup1.cif
contains datablock 1. DOI:https://doi.org/10.1107/S2052252518001379/lc5095sup2.cif
contains datablock 2. DOI:https://doi.org/10.1107/S2052252518001379/lc5095sup3.cif
contains datablock 3. DOI:https://doi.org/10.1107/S2052252518001379/lc5095sup4.cif
contains datablock 4. DOI:https://doi.org/10.1107/S2052252518001379/lc5095sup5.cif
contains datablock 5. DOI:https://doi.org/10.1107/S2052252518001379/lc5095sup6.cif
contains datablock 6. DOI:Structure factors: contains datablock 3. DOI: https://doi.org/10.1107/S2052252518001379/lc50953sup7.hkl
Structure refinements, tables, spectra and figures. DOI: https://doi.org/10.1107/S2052252518001379/lc5095sup8.pdf
Data collection: Bruker APEX2; cell
Bruker SAINT; data reduction: Bruker SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2014); molecular graphics: Bruker SHELXTL; software used to prepare material for publication: Bruker SHELXTL.C56H40N4O8Zn2 | F(000) = 2112 |
Mr = 1027.66 | Dx = 1.120 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 20.3028 (9) Å | Cell parameters from 9779 reflections |
b = 19.3686 (9) Å | θ = 2.3–28.2° |
c = 15.9389 (7) Å | µ = 0.84 mm−1 |
β = 103.500 (2)° | T = 100 K |
V = 6094.6 (5) Å3 | Block, pale_yellow |
Z = 4 | 0.31 × 0.25 × 0.19 mm |
Bruker D8 Venture diffractometer | 10294 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.038 |
Absorption correction: multi-scan SADABS (Sheldrick, 2011) | θmax = 26.0°, θmin = 2.1° |
Tmin = 0.688, Tmax = 0.746 | h = −25→25 |
128744 measured reflections | k = −23→23 |
11944 independent reflections | l = −19→19 |
Refinement on F2 | 56 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.072 | H-atom parameters constrained |
wR(F2) = 0.161 | w = 1/[σ2(Fo2) + (0.0319P)2 + 24.952P] where P = (Fo2 + 2Fc2)/3 |
S = 1.18 | (Δ/σ)max = 0.001 |
11944 reflections | Δρmax = 1.67 e Å−3 |
817 parameters | Δρmin = −0.56 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Our initial attempt to refine the structure using the normal data was not satisfactory and hence the data were SQUEEZED. O4 was disordered with occupancies fixed at 0.6 and 0.4. Anisotropic thermal parameters were refined for these two O atoms without any restraints/constraints. The two bpeb ligands were disordered. Two disorder components were included and a common occupancy was refined to 0.605 (6). Anisotropic thermal parameters were refined for all the non-hydrogen atoms in the major component. Soft constraints like FLAT SAME were used for some of the phenyl and pyridyl rings. For the non-hydrogen atoms in the minor disorder, only isotropic thermal parameter could be refined after all the options tried. Again, FLAT and SAME were used to retain a reasonably ideal geometry of few phenyl and pyridyl rings. The agreement factors are much better for this data as compared to the normal data. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Zn1 | 0.83225 (2) | 0.44184 (2) | 0.63870 (3) | 0.02214 (13) | |
Zn2 | 0.81884 (2) | 0.55904 (2) | 0.83594 (3) | 0.02146 (12) | |
O1 | 0.82995 (17) | 0.54032 (15) | 0.6033 (2) | 0.0381 (8) | |
O2 | 0.79866 (16) | 0.59234 (18) | 0.7127 (2) | 0.0377 (8) | |
O3 | 0.8232 (2) | 0.8448 (2) | 0.3830 (4) | 0.0789 (17) | |
O4 | 0.8256 (4) | 0.9034 (4) | 0.4865 (5) | 0.0385 (17) | 0.6 |
O4A | 0.8096 (8) | 0.9119 (6) | 0.5190 (8) | 0.049 (3) | 0.4 |
O5 | 0.81994 (17) | 0.46003 (15) | 0.8719 (2) | 0.0371 (8) | |
O6 | 0.84739 (17) | 0.40779 (18) | 0.7610 (2) | 0.0398 (8) | |
O7 | 0.8215 (2) | 0.1502 (2) | 1.0832 (4) | 0.0719 (15) | |
O8 | 0.8360 (3) | 0.0910 (2) | 0.9703 (4) | 0.0917 (19) | |
N1 | 0.7208 (10) | 0.4465 (9) | 0.6250 (10) | 0.031 (3) | 0.605 (6) |
C1 | 0.6942 (9) | 0.3906 (9) | 0.6755 (11) | 0.043 (4) | 0.605 (6) |
H1 | 0.7247 | 0.3577 | 0.7076 | 0.051* | 0.605 (6) |
C2 | 0.6296 (6) | 0.3873 (9) | 0.6752 (9) | 0.040 (3) | 0.605 (6) |
H2 | 0.6131 | 0.3473 | 0.6982 | 0.048* | 0.605 (6) |
C3 | 0.5839 (7) | 0.4404 (8) | 0.6425 (9) | 0.042 (3) | 0.605 (6) |
C4 | 0.6111 (5) | 0.4914 (7) | 0.6018 (9) | 0.044 (3) | 0.605 (6) |
H4 | 0.5836 | 0.5288 | 0.5757 | 0.053* | 0.605 (6) |
C5 | 0.6778 (8) | 0.4888 (7) | 0.5985 (10) | 0.045 (3) | 0.605 (6) |
H5 | 0.6926 | 0.5271 | 0.5704 | 0.054* | 0.605 (6) |
C6 | 0.5142 (5) | 0.4465 (8) | 0.6460 (6) | 0.052 (3) | 0.605 (6) |
H6 | 0.4901 | 0.4856 | 0.6187 | 0.062* | 0.605 (6) |
C7 | 0.4813 (5) | 0.4034 (7) | 0.6831 (6) | 0.048 (3) | 0.605 (6) |
H7 | 0.5059 | 0.3647 | 0.7108 | 0.058* | 0.605 (6) |
C8 | 0.4085 (4) | 0.4084 (7) | 0.6869 (6) | 0.049 (3) | 0.605 (6) |
C9 | 0.3825 (5) | 0.3541 (7) | 0.7317 (7) | 0.061 (3) | 0.605 (6) |
H9 | 0.4117 | 0.3184 | 0.7592 | 0.073* | 0.605 (6) |
C10 | 0.3147 (5) | 0.3541 (6) | 0.7350 (6) | 0.057 (3) | 0.605 (6) |
H10 | 0.2979 | 0.3179 | 0.7644 | 0.069* | 0.605 (6) |
C11 | 0.2708 (5) | 0.4068 (7) | 0.6952 (6) | 0.053 (3) | 0.605 (6) |
C12 | 0.2969 (5) | 0.4597 (7) | 0.6532 (7) | 0.057 (3) | 0.605 (6) |
H12 | 0.2686 | 0.4969 | 0.6281 | 0.069* | 0.605 (6) |
C13 | 0.3648 (5) | 0.4579 (7) | 0.6481 (7) | 0.064 (3) | 0.605 (6) |
H13 | 0.3809 | 0.4929 | 0.6161 | 0.077* | 0.605 (6) |
C14 | 0.2001 (4) | 0.4054 (6) | 0.7003 (5) | 0.053 (3) | 0.605 (6) |
H14 | 0.1868 | 0.3691 | 0.7328 | 0.064* | 0.605 (6) |
C15 | 0.1543 (5) | 0.4486 (6) | 0.6647 (6) | 0.044 (2) | 0.605 (6) |
H15 | 0.1690 | 0.4865 | 0.6358 | 0.052* | 0.605 (6) |
N2 | −0.0630 (11) | 0.4460 (6) | 0.6508 (10) | 0.026 (3) | 0.605 (6) |
C16 | −0.0175 (7) | 0.3994 (7) | 0.6993 (9) | 0.034 (3) | 0.605 (6) |
H16 | −0.0356 | 0.3652 | 0.7302 | 0.040* | 0.605 (6) |
C17 | 0.0515 (5) | 0.3984 (7) | 0.7067 (7) | 0.038 (3) | 0.605 (6) |
H17 | 0.0786 | 0.3644 | 0.7416 | 0.046* | 0.605 (6) |
C18 | 0.0814 (6) | 0.4466 (6) | 0.6634 (6) | 0.033 (2) | 0.605 (6) |
C19 | 0.0381 (5) | 0.4937 (6) | 0.6150 (9) | 0.032 (2) | 0.605 (6) |
H19 | 0.0561 | 0.5283 | 0.5845 | 0.038* | 0.605 (6) |
C20 | −0.0297 (7) | 0.4927 (7) | 0.6094 (10) | 0.031 (3) | 0.605 (6) |
H20 | −0.0564 | 0.5268 | 0.5742 | 0.037* | 0.605 (6) |
N3 | 0.7070 (5) | 0.5613 (6) | 0.8221 (7) | 0.020 (2) | 0.605 (6) |
C21 | 0.6715 (5) | 0.6141 (6) | 0.7798 (7) | 0.033 (2) | 0.605 (6) |
H21 | 0.6938 | 0.6466 | 0.7515 | 0.040* | 0.605 (6) |
C22 | 0.6057 (5) | 0.6224 (7) | 0.7762 (7) | 0.043 (2) | 0.605 (6) |
H22 | 0.5818 | 0.6595 | 0.7438 | 0.051* | 0.605 (6) |
C23 | 0.5719 (4) | 0.5777 (6) | 0.8189 (6) | 0.0323 (19) | 0.605 (6) |
C24 | 0.6102 (5) | 0.5260 (7) | 0.8646 (8) | 0.055 (3) | 0.605 (6) |
H24 | 0.5902 | 0.4943 | 0.8967 | 0.066* | 0.605 (6) |
C25 | 0.6776 (7) | 0.5200 (7) | 0.8642 (10) | 0.055 (4) | 0.605 (6) |
H25 | 0.7033 | 0.4838 | 0.8963 | 0.066* | 0.605 (6) |
C26 | 0.5004 (4) | 0.5901 (7) | 0.8174 (6) | 0.044 (2) | 0.605 (6) |
H26 | 0.4808 | 0.6299 | 0.7866 | 0.052* | 0.605 (6) |
C27 | 0.4605 (6) | 0.5537 (11) | 0.8525 (9) | 0.070 (5) | 0.605 (6) |
H27 | 0.4801 | 0.5137 | 0.8827 | 0.083* | 0.605 (6) |
C28 | 0.3903 (4) | 0.5658 (5) | 0.8521 (5) | 0.050 (3) | 0.605 (6) |
C29 | 0.3534 (4) | 0.6241 (6) | 0.8174 (5) | 0.057 (3) | 0.605 (6) |
H29 | 0.3759 | 0.6607 | 0.7957 | 0.068* | 0.605 (6) |
C30 | 0.2841 (4) | 0.6300 (7) | 0.8139 (6) | 0.064 (4) | 0.605 (6) |
H30 | 0.2605 | 0.6704 | 0.7901 | 0.077* | 0.605 (6) |
C31 | 0.2501 (5) | 0.5785 (6) | 0.8440 (5) | 0.061 (4) | 0.605 (6) |
C32 | 0.2867 (6) | 0.5217 (7) | 0.8810 (7) | 0.064 (4) | 0.605 (6) |
H32 | 0.2645 | 0.4866 | 0.9056 | 0.077* | 0.605 (6) |
C33 | 0.3555 (5) | 0.5146 (7) | 0.8834 (7) | 0.062 (3) | 0.605 (6) |
H33 | 0.3786 | 0.4738 | 0.9069 | 0.074* | 0.605 (6) |
C34 | 0.1771 (4) | 0.5874 (6) | 0.8342 (5) | 0.052 (3) | 0.605 (6) |
H34 | 0.1578 | 0.6285 | 0.8063 | 0.062* | 0.605 (6) |
C35 | 0.1387 (5) | 0.5482 (5) | 0.8577 (6) | 0.047 (2) | 0.605 (6) |
H35 | 0.1593 | 0.5068 | 0.8831 | 0.056* | 0.605 (6) |
N4 | −0.0713 (8) | 0.5562 (6) | 0.8478 (8) | 0.025 (3) | 0.605 (6) |
C36 | −0.0421 (6) | 0.6044 (7) | 0.8070 (8) | 0.029 (3) | 0.605 (6) |
H36 | −0.0697 | 0.6400 | 0.7762 | 0.035* | 0.605 (6) |
C37 | 0.0250 (5) | 0.6040 (6) | 0.8082 (7) | 0.032 (3) | 0.605 (6) |
H37 | 0.0432 | 0.6385 | 0.7777 | 0.038* | 0.605 (6) |
C38 | 0.0671 (6) | 0.5531 (6) | 0.8540 (6) | 0.032 (2) | 0.605 (6) |
C39 | 0.0356 (5) | 0.5040 (6) | 0.8947 (8) | 0.031 (3) | 0.605 (6) |
H39 | 0.0616 | 0.4677 | 0.9263 | 0.038* | 0.605 (6) |
C40 | −0.0304 (7) | 0.5073 (6) | 0.8902 (9) | 0.028 (3) | 0.605 (6) |
H40 | −0.0498 | 0.4725 | 0.9189 | 0.033* | 0.605 (6) |
N1Z | 0.7253 (14) | 0.4391 (15) | 0.6393 (15) | 0.019 (5)* | 0.395 (6) |
C1Z | 0.6966 (18) | 0.4017 (15) | 0.6636 (17) | 0.040 (7)* | 0.395 (6) |
H1Z | 0.7187 | 0.3592 | 0.6817 | 0.048* | 0.395 (6) |
C2Z | 0.6218 (17) | 0.4083 (13) | 0.673 (2) | 0.051 (8)* | 0.395 (6) |
H2Z | 0.6026 | 0.3784 | 0.7082 | 0.061* | 0.395 (6) |
C3Z | 0.5876 (14) | 0.4603 (12) | 0.6269 (16) | 0.038 (6)* | 0.395 (6) |
C4Z | 0.6165 (11) | 0.5049 (11) | 0.5782 (12) | 0.038 (5)* | 0.395 (6) |
H4Z | 0.5899 | 0.5389 | 0.5427 | 0.045* | 0.395 (6) |
C5Z | 0.6854 (11) | 0.4989 (10) | 0.5822 (12) | 0.024 (4)* | 0.395 (6) |
H5Z | 0.7077 | 0.5298 | 0.5517 | 0.029* | 0.395 (6) |
C6Z | 0.5132 (9) | 0.4694 (9) | 0.6208 (12) | 0.047 (5)* | 0.395 (6) |
H6Z | 0.4899 | 0.5022 | 0.5801 | 0.056* | 0.395 (6) |
C7Z | 0.4783 (11) | 0.4367 (10) | 0.6659 (13) | 0.051 (5)* | 0.395 (6) |
H7Z | 0.5018 | 0.4014 | 0.7022 | 0.061* | 0.395 (6) |
C8Z | 0.4066 (9) | 0.4466 (7) | 0.6689 (9) | 0.042 (4)* | 0.395 (6) |
C9Z | 0.3761 (8) | 0.3960 (8) | 0.7099 (9) | 0.048 (4)* | 0.395 (6) |
H9Z | 0.4025 | 0.3585 | 0.7378 | 0.057* | 0.395 (6) |
C10Z | 0.3086 (7) | 0.3997 (7) | 0.7107 (8) | 0.033 (3)* | 0.395 (6) |
H10Z | 0.2890 | 0.3651 | 0.7395 | 0.040* | 0.395 (6) |
C11Z | 0.2686 (7) | 0.4543 (6) | 0.6690 (8) | 0.027 (3)* | 0.395 (6) |
C12Z | 0.3010 (7) | 0.5050 (8) | 0.6293 (10) | 0.051 (4)* | 0.395 (6) |
H12Z | 0.2749 | 0.5426 | 0.6011 | 0.061* | 0.395 (6) |
C13Z | 0.3687 (8) | 0.5022 (9) | 0.6299 (11) | 0.058 (4)* | 0.395 (6) |
H13Z | 0.3892 | 0.5379 | 0.6039 | 0.069* | 0.395 (6) |
C14Z | 0.1979 (6) | 0.4602 (6) | 0.6605 (7) | 0.028 (2)* | 0.395 (6) |
H14Z | 0.1765 | 0.4985 | 0.6282 | 0.033* | 0.395 (6) |
C15Z | 0.1551 (7) | 0.4155 (8) | 0.6945 (9) | 0.035 (3)* | 0.395 (6) |
H15Z | 0.1749 | 0.3769 | 0.7278 | 0.042* | 0.395 (6) |
N2Z | −0.0560 (16) | 0.4376 (9) | 0.6590 (15) | 0.016 (4)* | 0.395 (6) |
C16Z | −0.0262 (10) | 0.3854 (9) | 0.7013 (12) | 0.018 (4)* | 0.395 (6) |
H16Z | −0.0517 | 0.3521 | 0.7239 | 0.021* | 0.395 (6) |
C17Z | 0.0447 (9) | 0.3777 (7) | 0.7139 (11) | 0.022 (4)* | 0.395 (6) |
H17Z | 0.0667 | 0.3392 | 0.7453 | 0.027* | 0.395 (6) |
C18Z | 0.0821 (9) | 0.4260 (7) | 0.6809 (9) | 0.018 (3)* | 0.395 (6) |
C19Z | 0.0469 (10) | 0.4813 (11) | 0.6367 (12) | 0.027 (5)* | 0.395 (6) |
H19Z | 0.0700 | 0.5167 | 0.6139 | 0.033* | 0.395 (6) |
C20Z | −0.0242 (11) | 0.4839 (11) | 0.6261 (13) | 0.019 (5)* | 0.395 (6) |
H20Z | −0.0490 | 0.5207 | 0.5941 | 0.022* | 0.395 (6) |
N3Z | 0.7198 (11) | 0.5526 (13) | 0.8313 (16) | 0.037 (6)* | 0.395 (6) |
C21Z | 0.6682 (11) | 0.5900 (10) | 0.7793 (14) | 0.041 (6)* | 0.395 (6) |
H21Z | 0.6820 | 0.6178 | 0.7373 | 0.050* | 0.395 (6) |
C22Z | 0.5972 (12) | 0.5941 (11) | 0.7775 (17) | 0.060 (7)* | 0.395 (6) |
H22Z | 0.5674 | 0.6250 | 0.7406 | 0.072* | 0.395 (6) |
C23Z | 0.5750 (11) | 0.5488 (9) | 0.8350 (12) | 0.039 (5)* | 0.395 (6) |
C24Z | 0.6203 (9) | 0.5042 (8) | 0.8833 (11) | 0.037 (4)* | 0.395 (6) |
H24Z | 0.6055 | 0.4724 | 0.9204 | 0.044* | 0.395 (6) |
C25Z | 0.6872 (11) | 0.5046 (10) | 0.8792 (13) | 0.037 (5)* | 0.395 (6) |
H25Z | 0.7152 | 0.4698 | 0.9111 | 0.045* | 0.395 (6) |
C26Z | 0.4979 (12) | 0.5554 (12) | 0.8316 (14) | 0.065 (6)* | 0.395 (6) |
H26Z | 0.4729 | 0.5900 | 0.7955 | 0.079* | 0.395 (6) |
C27Z | 0.4710 (18) | 0.5226 (16) | 0.868 (2) | 0.095 (12)* | 0.395 (6) |
H27Z | 0.4976 | 0.4889 | 0.9041 | 0.115* | 0.395 (6) |
C28Z | 0.3938 (10) | 0.5243 (8) | 0.8692 (10) | 0.053 (4)* | 0.395 (6) |
C29Z | 0.3543 (10) | 0.5730 (10) | 0.8254 (11) | 0.069 (5)* | 0.395 (6) |
H29Z | 0.3734 | 0.6060 | 0.7939 | 0.082* | 0.395 (6) |
C30Z | 0.2828 (10) | 0.5772 (10) | 0.8243 (12) | 0.071 (5)* | 0.395 (6) |
H30Z | 0.2548 | 0.6123 | 0.7930 | 0.085* | 0.395 (6) |
C31Z | 0.2576 (9) | 0.5281 (8) | 0.8707 (11) | 0.041 (4)* | 0.395 (6) |
C32Z | 0.2992 (7) | 0.4778 (8) | 0.9142 (10) | 0.046 (3)* | 0.395 (6) |
H32Z | 0.2809 | 0.4429 | 0.9439 | 0.055* | 0.395 (6) |
C33Z | 0.3701 (8) | 0.4770 (9) | 0.9157 (11) | 0.061 (4)* | 0.395 (6) |
H33Z | 0.3994 | 0.4438 | 0.9489 | 0.074* | 0.395 (6) |
C34Z | 0.1848 (6) | 0.5299 (6) | 0.8738 (7) | 0.027 (2)* | 0.395 (6) |
H34Z | 0.1706 | 0.4953 | 0.9080 | 0.032* | 0.395 (6) |
C35Z | 0.1333 (8) | 0.5778 (8) | 0.8312 (9) | 0.036 (3)* | 0.395 (6) |
H35Z | 0.1457 | 0.6144 | 0.7983 | 0.043* | 0.395 (6) |
N4Z | −0.0781 (12) | 0.5644 (10) | 0.8375 (12) | 0.015 (4)* | 0.395 (6) |
C36Z | −0.0525 (10) | 0.6166 (10) | 0.8028 (12) | 0.022 (5)* | 0.395 (6) |
H36Z | −0.0827 | 0.6519 | 0.7758 | 0.026* | 0.395 (6) |
C37Z | 0.0172 (9) | 0.6238 (8) | 0.8030 (11) | 0.022 (4)* | 0.395 (6) |
H37Z | 0.0330 | 0.6640 | 0.7798 | 0.027* | 0.395 (6) |
C38Z | 0.0613 (11) | 0.5717 (8) | 0.8371 (10) | 0.019 (4)* | 0.395 (6) |
C39Z | 0.0357 (10) | 0.5189 (10) | 0.8778 (13) | 0.032 (5)* | 0.395 (6) |
H39Z | 0.0647 | 0.4836 | 0.9071 | 0.039* | 0.395 (6) |
C40Z | −0.0344 (12) | 0.5179 (13) | 0.8756 (13) | 0.026 (6)* | 0.395 (6) |
H40Z | −0.0509 | 0.4808 | 0.9038 | 0.031* | 0.395 (6) |
C41 | 0.8141 (2) | 0.5920 (2) | 0.6407 (3) | 0.0261 (9) | |
C42 | 0.8130 (2) | 0.6603 (2) | 0.5955 (2) | 0.0221 (8) | |
C43 | 0.8113 (2) | 0.7222 (2) | 0.6393 (3) | 0.0300 (9) | |
H43 | 0.8088 | 0.7221 | 0.6980 | 0.036* | |
C44 | 0.8134 (2) | 0.7845 (2) | 0.5958 (3) | 0.0396 (12) | |
H44 | 0.8126 | 0.8270 | 0.6252 | 0.048* | |
C45 | 0.8167 (2) | 0.7843 (2) | 0.5095 (3) | 0.0372 (11) | |
C46 | 0.8177 (2) | 0.7225 (2) | 0.4673 (3) | 0.0350 (10) | |
H46 | 0.8188 | 0.7225 | 0.4080 | 0.042* | |
C47 | 0.8171 (2) | 0.6606 (2) | 0.5098 (3) | 0.0291 (9) | |
H47 | 0.8194 | 0.6183 | 0.4805 | 0.035* | |
C48 | 0.8202 (3) | 0.8516 (3) | 0.4612 (5) | 0.062 (2) | |
C49 | 0.83203 (19) | 0.4079 (2) | 0.8321 (3) | 0.0242 (8) | |
C50 | 0.82906 (19) | 0.3392 (2) | 0.8760 (3) | 0.0214 (8) | |
C51 | 0.8212 (2) | 0.3376 (2) | 0.9595 (3) | 0.0301 (9) | |
H51 | 0.8161 | 0.3795 | 0.9883 | 0.036* | |
C52 | 0.8206 (3) | 0.2751 (2) | 1.0013 (3) | 0.0374 (11) | |
H52 | 0.8154 | 0.2742 | 1.0590 | 0.045* | |
C53 | 0.8278 (2) | 0.2138 (2) | 0.9593 (3) | 0.0357 (11) | |
C54 | 0.8344 (3) | 0.2155 (2) | 0.8750 (3) | 0.0386 (11) | |
H54 | 0.8378 | 0.1735 | 0.8455 | 0.046* | |
C55 | 0.8362 (2) | 0.2773 (2) | 0.8334 (3) | 0.0318 (10) | |
H55 | 0.8421 | 0.2781 | 0.7760 | 0.038* | |
C56 | 0.8280 (2) | 0.1454 (3) | 1.0058 (5) | 0.0573 (18) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0301 (3) | 0.0138 (2) | 0.0250 (2) | −0.00096 (18) | 0.01170 (19) | −0.00135 (18) |
Zn2 | 0.0292 (3) | 0.0148 (2) | 0.0227 (2) | −0.00016 (18) | 0.01069 (18) | −0.00091 (17) |
O1 | 0.0436 (19) | 0.0156 (14) | 0.063 (2) | 0.0039 (13) | 0.0271 (17) | 0.0091 (14) |
O2 | 0.0347 (18) | 0.049 (2) | 0.0309 (16) | 0.0044 (15) | 0.0106 (14) | 0.0153 (15) |
O3 | 0.053 (3) | 0.077 (3) | 0.118 (4) | 0.021 (2) | 0.042 (3) | 0.078 (3) |
O4 | 0.044 (4) | 0.018 (4) | 0.052 (5) | 0.001 (3) | 0.009 (4) | 0.008 (4) |
O4A | 0.094 (11) | 0.012 (4) | 0.042 (7) | −0.003 (5) | 0.018 (6) | −0.004 (4) |
O5 | 0.047 (2) | 0.0170 (15) | 0.054 (2) | 0.0007 (13) | 0.0253 (16) | 0.0060 (14) |
O6 | 0.045 (2) | 0.046 (2) | 0.0342 (17) | 0.0055 (16) | 0.0213 (15) | 0.0188 (15) |
O7 | 0.043 (2) | 0.059 (3) | 0.127 (4) | 0.0237 (19) | 0.047 (3) | 0.067 (3) |
O8 | 0.097 (4) | 0.016 (2) | 0.138 (5) | −0.004 (2) | −0.020 (3) | 0.022 (2) |
N1 | 0.044 (6) | 0.026 (7) | 0.020 (6) | 0.000 (4) | 0.002 (5) | −0.001 (5) |
C1 | 0.038 (6) | 0.053 (8) | 0.036 (6) | −0.018 (5) | 0.007 (4) | 0.022 (5) |
C2 | 0.021 (5) | 0.054 (9) | 0.046 (6) | 0.001 (6) | 0.009 (4) | 0.000 (6) |
C3 | 0.034 (6) | 0.050 (8) | 0.041 (6) | −0.010 (6) | 0.009 (5) | −0.010 (6) |
C4 | 0.023 (5) | 0.046 (7) | 0.061 (8) | 0.007 (5) | 0.002 (5) | 0.011 (6) |
C5 | 0.045 (7) | 0.032 (6) | 0.060 (8) | −0.009 (5) | 0.016 (6) | 0.010 (5) |
C6 | 0.031 (5) | 0.094 (9) | 0.027 (5) | 0.006 (5) | 0.002 (4) | 0.012 (6) |
C7 | 0.028 (5) | 0.081 (9) | 0.033 (5) | −0.003 (5) | 0.003 (4) | −0.015 (5) |
C8 | 0.023 (4) | 0.080 (8) | 0.047 (5) | −0.013 (5) | 0.016 (4) | −0.017 (5) |
C9 | 0.025 (4) | 0.107 (10) | 0.055 (6) | −0.023 (5) | 0.018 (4) | −0.015 (6) |
C10 | 0.035 (5) | 0.087 (8) | 0.054 (6) | −0.019 (5) | 0.018 (4) | −0.015 (6) |
C11 | 0.031 (5) | 0.095 (9) | 0.035 (5) | −0.012 (5) | 0.012 (4) | −0.018 (5) |
C12 | 0.026 (5) | 0.097 (10) | 0.048 (6) | −0.007 (5) | 0.005 (4) | −0.009 (6) |
C13 | 0.021 (5) | 0.104 (10) | 0.069 (7) | −0.003 (5) | 0.016 (5) | −0.019 (7) |
C14 | 0.027 (5) | 0.100 (8) | 0.030 (4) | −0.013 (5) | 0.002 (3) | −0.025 (5) |
C15 | 0.045 (6) | 0.056 (6) | 0.034 (4) | −0.009 (5) | 0.017 (4) | −0.019 (4) |
N2 | 0.033 (7) | 0.021 (5) | 0.025 (5) | 0.009 (4) | 0.009 (4) | −0.001 (3) |
C16 | 0.037 (6) | 0.027 (6) | 0.040 (6) | −0.003 (5) | 0.016 (4) | −0.002 (5) |
C17 | 0.026 (5) | 0.039 (7) | 0.049 (6) | −0.002 (5) | 0.011 (4) | −0.012 (5) |
C18 | 0.047 (6) | 0.028 (5) | 0.026 (5) | −0.013 (5) | 0.012 (4) | −0.011 (4) |
C19 | 0.028 (5) | 0.035 (6) | 0.037 (7) | −0.010 (4) | 0.014 (5) | −0.006 (5) |
C20 | 0.034 (6) | 0.027 (6) | 0.035 (7) | −0.006 (4) | 0.014 (5) | 0.008 (5) |
N3 | 0.007 (4) | 0.032 (5) | 0.020 (4) | 0.004 (4) | 0.002 (3) | −0.009 (3) |
C21 | 0.027 (5) | 0.024 (5) | 0.047 (6) | 0.003 (4) | 0.004 (3) | 0.003 (4) |
C22 | 0.031 (5) | 0.050 (7) | 0.049 (6) | 0.004 (5) | 0.012 (4) | 0.003 (5) |
C23 | 0.026 (4) | 0.047 (6) | 0.023 (4) | −0.001 (4) | 0.004 (3) | −0.002 (4) |
C24 | 0.031 (6) | 0.060 (7) | 0.077 (8) | 0.014 (5) | 0.018 (5) | 0.034 (6) |
C25 | 0.036 (6) | 0.053 (7) | 0.076 (9) | 0.014 (5) | 0.013 (5) | 0.036 (6) |
C26 | 0.011 (4) | 0.074 (8) | 0.046 (5) | 0.005 (4) | 0.008 (3) | −0.001 (5) |
C27 | 0.029 (5) | 0.136 (16) | 0.049 (6) | −0.018 (8) | 0.020 (5) | −0.047 (9) |
C28 | 0.014 (4) | 0.092 (9) | 0.039 (5) | 0.006 (5) | −0.003 (3) | −0.019 (5) |
C29 | 0.025 (4) | 0.102 (9) | 0.045 (5) | 0.000 (5) | 0.011 (4) | −0.018 (5) |
C30 | 0.016 (4) | 0.122 (11) | 0.052 (6) | 0.011 (5) | 0.001 (4) | −0.033 (6) |
C31 | 0.024 (5) | 0.130 (12) | 0.030 (4) | 0.006 (6) | 0.008 (4) | −0.028 (6) |
C32 | 0.040 (7) | 0.118 (12) | 0.036 (5) | −0.022 (7) | 0.011 (5) | −0.012 (6) |
C33 | 0.026 (5) | 0.095 (9) | 0.066 (7) | 0.000 (5) | 0.012 (5) | −0.003 (6) |
C34 | 0.030 (5) | 0.101 (8) | 0.025 (4) | −0.030 (5) | 0.006 (3) | −0.023 (5) |
C35 | 0.067 (7) | 0.033 (5) | 0.035 (5) | 0.004 (5) | 0.000 (4) | −0.019 (4) |
N4 | 0.029 (6) | 0.017 (5) | 0.024 (5) | 0.009 (4) | −0.003 (4) | 0.005 (3) |
C36 | 0.022 (5) | 0.029 (6) | 0.035 (5) | 0.008 (4) | 0.005 (4) | 0.005 (4) |
C37 | 0.035 (6) | 0.022 (5) | 0.041 (5) | −0.006 (5) | 0.014 (4) | −0.003 (5) |
C38 | 0.032 (5) | 0.038 (6) | 0.023 (5) | 0.008 (5) | −0.001 (4) | −0.009 (4) |
C39 | 0.042 (6) | 0.018 (5) | 0.028 (5) | 0.007 (4) | −0.004 (4) | 0.003 (4) |
C40 | 0.037 (6) | 0.016 (5) | 0.023 (5) | 0.007 (4) | −0.009 (4) | 0.010 (4) |
C41 | 0.020 (2) | 0.024 (2) | 0.037 (2) | 0.0031 (16) | 0.0115 (17) | 0.0104 (18) |
C42 | 0.024 (2) | 0.0184 (19) | 0.0236 (19) | −0.0025 (15) | 0.0043 (16) | 0.0017 (15) |
C43 | 0.038 (2) | 0.025 (2) | 0.024 (2) | 0.0067 (18) | 0.0012 (18) | −0.0030 (17) |
C44 | 0.042 (3) | 0.017 (2) | 0.050 (3) | 0.0041 (19) | −0.008 (2) | −0.003 (2) |
C45 | 0.028 (2) | 0.023 (2) | 0.055 (3) | −0.0044 (18) | −0.003 (2) | 0.017 (2) |
C46 | 0.038 (3) | 0.037 (3) | 0.032 (2) | 0.001 (2) | 0.013 (2) | 0.012 (2) |
C47 | 0.038 (2) | 0.023 (2) | 0.028 (2) | −0.0003 (18) | 0.0109 (18) | −0.0012 (17) |
C48 | 0.022 (3) | 0.036 (3) | 0.114 (6) | −0.007 (2) | −0.010 (3) | 0.042 (4) |
C49 | 0.0160 (19) | 0.024 (2) | 0.034 (2) | 0.0000 (15) | 0.0077 (16) | 0.0048 (17) |
C50 | 0.0187 (19) | 0.0191 (19) | 0.026 (2) | −0.0036 (15) | 0.0052 (15) | 0.0009 (15) |
C51 | 0.043 (3) | 0.018 (2) | 0.031 (2) | 0.0009 (18) | 0.0110 (19) | 0.0032 (17) |
C52 | 0.047 (3) | 0.038 (3) | 0.029 (2) | 0.003 (2) | 0.011 (2) | 0.015 (2) |
C53 | 0.027 (2) | 0.021 (2) | 0.057 (3) | −0.0034 (17) | 0.004 (2) | 0.014 (2) |
C54 | 0.046 (3) | 0.017 (2) | 0.050 (3) | −0.0019 (19) | 0.005 (2) | −0.0030 (19) |
C55 | 0.034 (2) | 0.029 (2) | 0.033 (2) | 0.0071 (19) | 0.0088 (19) | −0.0034 (18) |
C56 | 0.023 (3) | 0.042 (3) | 0.102 (5) | −0.003 (2) | 0.005 (3) | 0.044 (3) |
Zn1—O7i | 1.980 (4) | N4—C36 | 1.351 (15) |
Zn1—O1 | 1.986 (3) | N4—Zn2vi | 2.195 (16) |
Zn1—O6 | 2.013 (3) | C36—C37 | 1.358 (15) |
Zn1—N2ii | 2.09 (2) | C37—C38 | 1.395 (13) |
Zn1—N1Z | 2.17 (3) | C38—C39 | 1.388 (14) |
Zn1—N2Zii | 2.22 (3) | C39—C40 | 1.326 (15) |
Zn1—N1 | 2.223 (19) | N1Z—C1Z | 1.06 (3) |
Zn2—N3Z | 2.00 (2) | N1Z—C5Z | 1.58 (3) |
Zn2—O5 | 2.000 (3) | C1Z—C2Z | 1.57 (5) |
Zn2—O3iii | 2.001 (4) | C2Z—C3Z | 1.34 (3) |
Zn2—O2 | 2.017 (3) | C3Z—C4Z | 1.38 (3) |
Zn2—N4Zii | 2.09 (2) | C3Z—C6Z | 1.50 (3) |
Zn2—N4ii | 2.195 (16) | C4Z—C5Z | 1.39 (3) |
Zn2—N3 | 2.230 (10) | C6Z—C7Z | 1.29 (3) |
Zn2—O4iii | 2.481 (8) | C7Z—C8Z | 1.48 (3) |
O1—C41 | 1.244 (5) | C8Z—C13Z | 1.384 (18) |
O2—C41 | 1.258 (5) | C8Z—C9Z | 1.400 (17) |
O3—C48 | 1.269 (9) | C9Z—C10Z | 1.376 (19) |
O3—Zn2iv | 2.001 (4) | C10Z—C11Z | 1.403 (15) |
O4—O4A | 0.693 (10) | C11Z—C12Z | 1.411 (16) |
O4—C48 | 1.078 (10) | C11Z—C14Z | 1.414 (19) |
O4—Zn2iv | 2.481 (8) | C12Z—C13Z | 1.373 (19) |
O4A—C48 | 1.534 (13) | C14Z—C15Z | 1.420 (18) |
O5—C49 | 1.246 (5) | C15Z—C18Z | 1.46 (2) |
O6—C49 | 1.242 (5) | N2Z—C20Z | 1.29 (3) |
O7—C56 | 1.273 (8) | N2Z—C16Z | 1.29 (2) |
O7—Zn1v | 1.980 (4) | N2Z—Zn1vi | 2.22 (3) |
O8—C56 | 1.226 (8) | C16Z—C17Z | 1.41 (2) |
N1—C5 | 1.20 (2) | C17Z—C18Z | 1.386 (15) |
N1—C1 | 1.52 (2) | C18Z—C19Z | 1.385 (16) |
C1—C2 | 1.31 (2) | C19Z—C20Z | 1.41 (3) |
C2—C3 | 1.40 (2) | N3Z—C21Z | 1.38 (3) |
C3—C4 | 1.366 (19) | N3Z—C25Z | 1.46 (3) |
C3—C6 | 1.434 (16) | C21Z—C22Z | 1.44 (3) |
C4—C5 | 1.368 (19) | C22Z—C23Z | 1.42 (3) |
C6—C7 | 1.296 (17) | C23Z—C24Z | 1.36 (2) |
C7—C8 | 1.497 (13) | C23Z—C26Z | 1.56 (3) |
C8—C13 | 1.354 (17) | C24Z—C25Z | 1.37 (3) |
C8—C9 | 1.438 (16) | C26Z—C27Z | 1.09 (4) |
C9—C10 | 1.388 (12) | C27Z—C28Z | 1.57 (4) |
C10—C11 | 1.407 (16) | C28Z—C29Z | 1.325 (19) |
C11—C12 | 1.393 (16) | C28Z—C33Z | 1.337 (19) |
C11—C14 | 1.456 (13) | C29Z—C30Z | 1.45 (2) |
C12—C13 | 1.402 (14) | C30Z—C31Z | 1.376 (19) |
C14—C15 | 1.281 (15) | C31Z—C32Z | 1.367 (17) |
C15—C18 | 1.475 (14) | C31Z—C34Z | 1.49 (2) |
N2—C20 | 1.385 (18) | C32Z—C33Z | 1.433 (19) |
N2—C16 | 1.391 (19) | C34Z—C35Z | 1.443 (18) |
N2—Zn1vi | 2.09 (2) | C35Z—C38Z | 1.49 (3) |
C16—C17 | 1.379 (16) | N4Z—C40Z | 1.31 (2) |
C17—C18 | 1.384 (13) | N4Z—C36Z | 1.32 (2) |
C18—C19 | 1.373 (14) | N4Z—Zn2vi | 2.09 (2) |
C19—C20 | 1.358 (16) | C36Z—C37Z | 1.42 (2) |
N3—C25 | 1.277 (18) | C37Z—C38Z | 1.375 (16) |
N3—C21 | 1.339 (16) | C38Z—C39Z | 1.376 (18) |
C21—C22 | 1.334 (14) | C39Z—C40Z | 1.42 (3) |
C22—C23 | 1.379 (16) | C41—C42 | 1.506 (5) |
C23—C24 | 1.368 (15) | C42—C47 | 1.388 (6) |
C23—C26 | 1.466 (11) | C42—C43 | 1.391 (6) |
C24—C25 | 1.376 (17) | C43—C44 | 1.396 (6) |
C26—C27 | 1.30 (2) | C44—C45 | 1.393 (7) |
C27—C28 | 1.441 (14) | C45—C46 | 1.375 (7) |
C28—C33 | 1.377 (13) | C45—C48 | 1.524 (6) |
C28—C29 | 1.396 (12) | C46—C47 | 1.378 (6) |
C29—C30 | 1.399 (10) | C49—C50 | 1.512 (5) |
C30—C31 | 1.362 (14) | C50—C51 | 1.377 (6) |
C31—C32 | 1.381 (13) | C50—C55 | 1.402 (6) |
C31—C34 | 1.463 (12) | C51—C52 | 1.384 (6) |
C32—C33 | 1.395 (13) | C52—C53 | 1.387 (7) |
C34—C35 | 1.209 (14) | C53—C54 | 1.382 (7) |
C35—C38 | 1.445 (16) | C53—C56 | 1.518 (6) |
N4—C40 | 1.334 (14) | C54—C55 | 1.374 (6) |
O7i—Zn1—O1 | 138.2 (2) | C36—N4—Zn2vi | 119.5 (9) |
O7i—Zn1—O6 | 96.6 (2) | N4—C36—C37 | 122.7 (12) |
O1—Zn1—O6 | 125.28 (15) | C36—C37—C38 | 120.1 (10) |
O7i—Zn1—N2ii | 94.6 (4) | C39—C38—C37 | 115.8 (10) |
O1—Zn1—N2ii | 86.8 (3) | C39—C38—C35 | 120.3 (9) |
O6—Zn1—N2ii | 90.1 (4) | C37—C38—C35 | 123.8 (11) |
O7i—Zn1—N1Z | 88.5 (8) | C40—C39—C38 | 120.8 (10) |
O1—Zn1—N1Z | 93.9 (8) | C39—C40—N4 | 124.2 (13) |
O6—Zn1—N1Z | 85.1 (6) | C1Z—N1Z—C5Z | 117 (3) |
O7i—Zn1—N2Zii | 92.0 (6) | C1Z—N1Z—Zn1 | 131 (3) |
O1—Zn1—N2Zii | 91.8 (4) | C5Z—N1Z—Zn1 | 111.0 (16) |
O6—Zn1—N2Zii | 85.8 (5) | N1Z—C1Z—C2Z | 128 (3) |
N1Z—Zn1—N2Zii | 170.9 (8) | C3Z—C2Z—C1Z | 113 (3) |
O7i—Zn1—N1 | 89.4 (5) | C2Z—C3Z—C4Z | 123 (3) |
O1—Zn1—N1 | 88.7 (5) | C2Z—C3Z—C6Z | 121 (3) |
O6—Zn1—N1 | 91.7 (4) | C4Z—C3Z—C6Z | 116 (2) |
N2ii—Zn1—N1 | 175.4 (6) | C3Z—C4Z—C5Z | 118 (2) |
N3Z—Zn2—O5 | 83.9 (7) | C4Z—C5Z—N1Z | 117.7 (17) |
N3Z—Zn2—O3iii | 91.6 (7) | C7Z—C6Z—C3Z | 125.6 (19) |
O5—Zn2—O3iii | 142.0 (2) | C6Z—C7Z—C8Z | 128.9 (17) |
N3Z—Zn2—O2 | 90.6 (7) | C13Z—C8Z—C9Z | 119.7 (17) |
O5—Zn2—O2 | 124.86 (14) | C13Z—C8Z—C7Z | 122.3 (14) |
O3iii—Zn2—O2 | 92.8 (2) | C9Z—C8Z—C7Z | 118.0 (14) |
N3Z—Zn2—N4Zii | 178.4 (9) | C10Z—C9Z—C8Z | 121.2 (14) |
O5—Zn2—N4Zii | 95.7 (5) | C9Z—C10Z—C11Z | 120.2 (13) |
O3iii—Zn2—N4Zii | 89.6 (6) | C10Z—C11Z—C12Z | 117.2 (14) |
O2—Zn2—N4Zii | 88.4 (5) | C10Z—C11Z—C14Z | 124.6 (13) |
O5—Zn2—N4ii | 90.5 (3) | C12Z—C11Z—C14Z | 118.1 (10) |
O3iii—Zn2—N4ii | 92.0 (4) | C13Z—C12Z—C11Z | 122.8 (14) |
O2—Zn2—N4ii | 93.6 (3) | C12Z—C13Z—C8Z | 118.9 (15) |
O5—Zn2—N3 | 89.4 (3) | C11Z—C14Z—C15Z | 127.8 (12) |
O3iii—Zn2—N3 | 88.5 (3) | C14Z—C15Z—C18Z | 123.2 (13) |
O2—Zn2—N3 | 85.8 (3) | C20Z—N2Z—C16Z | 123 (3) |
N4ii—Zn2—N3 | 179.2 (5) | C20Z—N2Z—Zn1vi | 120.6 (17) |
N3Z—Zn2—O4iii | 83.2 (7) | C16Z—N2Z—Zn1vi | 116.4 (16) |
O5—Zn2—O4iii | 90.6 (2) | N2Z—C16Z—C17Z | 119.7 (19) |
O3iii—Zn2—O4iii | 51.5 (2) | C18Z—C17Z—C16Z | 120.4 (14) |
O2—Zn2—O4iii | 143.3 (2) | C19Z—C18Z—C17Z | 116.8 (16) |
N4Zii—Zn2—O4iii | 98.3 (6) | C19Z—C18Z—C15Z | 124.7 (15) |
N4ii—Zn2—O4iii | 95.6 (4) | C17Z—C18Z—C15Z | 118.5 (13) |
N3—Zn2—O4iii | 85.1 (3) | C18Z—C19Z—C20Z | 118.7 (16) |
C41—O1—Zn1 | 128.9 (3) | N2Z—C20Z—C19Z | 121.5 (19) |
C41—O2—Zn2 | 148.1 (3) | C21Z—N3Z—C25Z | 106.0 (19) |
C48—O3—Zn2iv | 105.3 (4) | C21Z—N3Z—Zn2 | 127.2 (18) |
O4A—O4—C48 | 118.5 (18) | C25Z—N3Z—Zn2 | 126.7 (16) |
O4A—O4—Zn2iv | 136.4 (17) | N3Z—C21Z—C22Z | 131 (2) |
C48—O4—Zn2iv | 86.1 (6) | C23Z—C22Z—C21Z | 115 (2) |
O4—O4A—C48 | 38.2 (12) | C24Z—C23Z—C22Z | 118.9 (18) |
C49—O5—Zn2 | 128.4 (3) | C24Z—C23Z—C26Z | 127.7 (17) |
C49—O6—Zn1 | 150.2 (3) | C22Z—C23Z—C26Z | 113 (2) |
C56—O7—Zn1v | 110.0 (4) | C23Z—C24Z—C25Z | 120.9 (17) |
C5—N1—C1 | 110.7 (16) | C24Z—C25Z—N3Z | 127.1 (18) |
C5—N1—Zn1 | 134.6 (13) | C27Z—C26Z—C23Z | 124 (3) |
C1—N1—Zn1 | 113.5 (11) | C26Z—C27Z—C28Z | 128 (3) |
C2—C1—N1 | 120.7 (16) | C29Z—C28Z—C33Z | 122 (2) |
C1—C2—C3 | 122.7 (15) | C29Z—C28Z—C27Z | 119.4 (19) |
C4—C3—C2 | 113.6 (11) | C33Z—C28Z—C27Z | 118.7 (17) |
C4—C3—C6 | 118.1 (14) | C28Z—C29Z—C30Z | 121.8 (18) |
C2—C3—C6 | 128.3 (14) | C31Z—C30Z—C29Z | 116.9 (16) |
C3—C4—C5 | 120.4 (12) | C32Z—C31Z—C30Z | 120.0 (18) |
N1—C5—C4 | 131.0 (14) | C32Z—C31Z—C34Z | 120.1 (12) |
C7—C6—C3 | 125.7 (13) | C30Z—C31Z—C34Z | 119.9 (15) |
C6—C7—C8 | 126.6 (12) | C31Z—C32Z—C33Z | 121.1 (15) |
C13—C8—C9 | 117.9 (10) | C28Z—C33Z—C32Z | 118.2 (16) |
C13—C8—C7 | 125.1 (11) | C35Z—C34Z—C31Z | 128.0 (12) |
C9—C8—C7 | 117.0 (11) | C34Z—C35Z—C38Z | 122.2 (14) |
C10—C9—C8 | 120.1 (12) | C40Z—N4Z—C36Z | 116 (2) |
C9—C10—C11 | 120.8 (11) | C40Z—N4Z—Zn2vi | 122.7 (15) |
C12—C11—C10 | 118.6 (10) | C36Z—N4Z—Zn2vi | 121.7 (15) |
C12—C11—C14 | 122.0 (12) | N4Z—C36Z—C37Z | 124.4 (17) |
C10—C11—C14 | 119.4 (10) | C38Z—C37Z—C36Z | 119.1 (16) |
C11—C12—C13 | 120.0 (12) | C37Z—C38Z—C39Z | 116.6 (18) |
C8—C13—C12 | 122.6 (12) | C37Z—C38Z—C35Z | 118.3 (14) |
C15—C14—C11 | 125.9 (11) | C39Z—C38Z—C35Z | 124.9 (16) |
C14—C15—C18 | 127.7 (11) | C38Z—C39Z—C40Z | 119.1 (16) |
C20—N2—C16 | 110.7 (16) | N4Z—C40Z—C39Z | 124.9 (19) |
C20—N2—Zn1vi | 125.5 (11) | O1—C41—O2 | 126.1 (4) |
C16—N2—Zn1vi | 123.7 (10) | O1—C41—C42 | 117.0 (4) |
C17—C16—N2 | 126.0 (12) | O2—C41—C42 | 116.9 (4) |
C16—C17—C18 | 120.2 (11) | C47—C42—C43 | 120.3 (4) |
C19—C18—C17 | 115.5 (10) | C47—C42—C41 | 118.5 (4) |
C19—C18—C15 | 120.0 (9) | C43—C42—C41 | 121.1 (4) |
C17—C18—C15 | 124.4 (11) | C42—C43—C44 | 119.2 (4) |
C20—C19—C18 | 122.3 (11) | C45—C44—C43 | 120.1 (4) |
C19—C20—N2 | 125.3 (14) | C46—C45—C44 | 119.7 (4) |
C25—N3—C21 | 118.7 (11) | C46—C45—C48 | 119.3 (5) |
C25—N3—Zn2 | 121.6 (10) | C44—C45—C48 | 121.0 (5) |
C21—N3—Zn2 | 118.8 (8) | C45—C46—C47 | 120.9 (4) |
C22—C21—N3 | 122.0 (11) | C46—C47—C42 | 119.7 (4) |
C21—C22—C23 | 120.8 (10) | O4—C48—O3 | 116.1 (7) |
C24—C23—C22 | 115.8 (9) | O4—C48—C45 | 128.3 (8) |
C24—C23—C26 | 124.5 (11) | O3—C48—C45 | 115.3 (6) |
C22—C23—C26 | 119.6 (10) | O4—C48—O4A | 23.4 (7) |
C23—C24—C25 | 120.1 (10) | O3—C48—O4A | 135.6 (6) |
N3—C25—C24 | 122.4 (12) | C45—C48—O4A | 108.6 (7) |
C27—C26—C23 | 128.4 (13) | O6—C49—O5 | 125.9 (4) |
C26—C27—C28 | 128.8 (17) | O6—C49—C50 | 117.7 (4) |
C33—C28—C29 | 116.9 (9) | O5—C49—C50 | 116.3 (4) |
C33—C28—C27 | 118.2 (12) | C51—C50—C55 | 119.8 (4) |
C29—C28—C27 | 124.8 (12) | C51—C50—C49 | 119.5 (4) |
C28—C29—C30 | 121.6 (10) | C55—C50—C49 | 120.6 (4) |
C31—C30—C29 | 120.9 (11) | C50—C51—C52 | 120.1 (4) |
C30—C31—C32 | 117.8 (10) | C51—C52—C53 | 120.2 (4) |
C30—C31—C34 | 117.4 (9) | C54—C53—C52 | 119.6 (4) |
C32—C31—C34 | 124.7 (10) | C54—C53—C56 | 120.4 (5) |
C31—C32—C33 | 121.7 (11) | C52—C53—C56 | 120.0 (5) |
C28—C33—C32 | 121.0 (10) | C55—C54—C53 | 120.6 (4) |
C35—C34—C31 | 127.1 (12) | C54—C55—C50 | 119.6 (4) |
C34—C35—C38 | 131.4 (12) | O8—C56—O7 | 124.4 (5) |
C40—N4—C36 | 116.3 (15) | O8—C56—C53 | 120.7 (6) |
C40—N4—Zn2vi | 124.1 (10) | O7—C56—C53 | 114.8 (6) |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x+1, y, z; (iii) x, −y+3/2, z+1/2; (iv) x, −y+3/2, z−1/2; (v) x, −y+1/2, z+1/2; (vi) x−1, y, z. |
C56H40N4O8Zn2 | Dx = 1.093 Mg m−3 |
Mr = 1027.66 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pcca | Cell parameters from 7985 reflections |
a = 19.490 (3) Å | θ = 2.3–21.6° |
b = 20.220 (3) Å | µ = 0.82 mm−1 |
c = 15.854 (2) Å | T = 173 K |
V = 6247.8 (15) Å3 | Plate, yellow |
Z = 4 | 0.20 × 0.15 × 0.08 mm |
F(000) = 2112 |
Bruker APEX-II CCD diffractometer | 3603 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.105 |
Absorption correction: multi-scan SADABS (Sheldrick, 2010) | θmax = 26.0°, θmin = 1.9° |
Tmin = 0.861, Tmax = 0.931 | h = −23→21 |
49542 measured reflections | k = −24→12 |
5982 independent reflections | l = −16→19 |
Refinement on F2 | 68 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.123 | H-atom parameters constrained |
wR(F2) = 0.383 | w = 1/[σ2(Fo2) + (0.1884P)2 + 22.1646P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
5982 reflections | Δρmax = 1.45 e Å−3 |
246 parameters | Δρmin = −1.02 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. It was not possible to locate the solvents in the lattice and the agreement factors were still unreasonably high (R1 = 0.2065) we have Squeezed the data.The bpeb ligand was disordered. Only the disorder component in the middle of the ligand (C8 to C15) was resolved. Two models were included and refined. Hard constraints were used to hold the geometry close to ideal. Only common isotropic thermal parameters were refined for each group of disorder. A common occupancy factor of the two disorder components were refined to 0.611 (17). From this data only the connectivity could be confirmed beyond any doubt and the bond distances and angles should be treated with caution. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Zn1 | 0.43808 (5) | 0.32954 (5) | 0.35173 (5) | 0.0496 (4) | |
O1 | 0.5342 (3) | 0.3326 (3) | 0.3893 (5) | 0.0791 (19) | |
O2 | 0.5880 (4) | 0.3246 (4) | 0.2725 (4) | 0.088 (2) | |
O3 | 0.8426 (5) | 0.3252 (4) | 0.6037 (8) | 0.122 (4) | |
O4 | 0.8996 (5) | 0.3278 (4) | 0.4963 (8) | 0.119 (4) | |
N1 | 0.4428 (3) | 0.2256 (3) | 0.3529 (4) | 0.070 (2) | |
C1 | 0.3984 (4) | 0.1898 (4) | 0.3017 (5) | 0.110 (4) | |
H1 | 0.3656 | 0.2123 | 0.2678 | 0.133* | |
C2 | 0.4018 (6) | 0.1212 (4) | 0.3001 (6) | 0.124 (5) | |
H2 | 0.3715 | 0.0967 | 0.2651 | 0.148* | |
C3 | 0.4498 (6) | 0.0883 (3) | 0.3496 (7) | 0.165 (9) | |
C4 | 0.4942 (5) | 0.1241 (4) | 0.4008 (7) | 0.142 (6) | |
H4 | 0.5270 | 0.1016 | 0.4347 | 0.170* | |
C5 | 0.4908 (4) | 0.1927 (4) | 0.4024 (5) | 0.100 (4) | |
H5 | 0.5211 | 0.2171 | 0.4374 | 0.120* | |
C6 | 0.4614 (14) | 0.0140 (8) | 0.3592 (15) | 0.203 (10)* | |
H6 | 0.5011 | 0.0025 | 0.3907 | 0.244* | |
C7 | 0.4308 (10) | −0.0299 (9) | 0.3351 (16) | 0.223 (12)* | |
H7 | 0.3895 | −0.0187 | 0.3067 | 0.268* | |
C8 | 0.4451 (8) | −0.1031 (4) | 0.3408 (12) | 0.115 (4)* | 0.611 (18) |
C9 | 0.3951 (7) | −0.1453 (5) | 0.3089 (12) | 0.115 (4)* | 0.611 (18) |
H9 | 0.3549 | −0.1276 | 0.2835 | 0.138* | 0.611 (18) |
C10 | 0.4038 (8) | −0.2134 (5) | 0.3142 (12) | 0.115 (4)* | 0.611 (18) |
H10 | 0.3696 | −0.2422 | 0.2924 | 0.138* | 0.611 (18) |
C11 | 0.4626 (8) | −0.2393 (4) | 0.3513 (12) | 0.115 (4)* | 0.611 (18) |
C12 | 0.5126 (7) | −0.1972 (6) | 0.3831 (11) | 0.115 (4)* | 0.611 (18) |
H12 | 0.5527 | −0.2149 | 0.4085 | 0.138* | 0.611 (18) |
C13 | 0.5038 (7) | −0.1291 (5) | 0.3779 (12) | 0.115 (4)* | 0.611 (18) |
H13 | 0.5380 | −0.1002 | 0.3997 | 0.138* | 0.611 (18) |
C14 | 0.4706 (11) | −0.3129 (8) | 0.3584 (14) | 0.115 (4)* | 0.611 (18) |
H14 | 0.5098 | −0.3287 | 0.3876 | 0.138* | 0.611 (18) |
C15 | 0.4342 (8) | −0.3513 (7) | 0.3321 (10) | 0.115 (4)* | 0.611 (18) |
H15 | 0.3962 | −0.3323 | 0.3033 | 0.138* | 0.611 (18) |
C8A | 0.4192 (12) | −0.1047 (5) | 0.3290 (19) | 0.120 (6)* | 0.389 (18) |
C9A | 0.3621 (11) | −0.1316 (6) | 0.2891 (18) | 0.120 (6)* | 0.389 (18) |
H9A | 0.3276 | −0.1033 | 0.2668 | 0.144* | 0.389 (18) |
C10A | 0.3555 (11) | −0.1998 (7) | 0.2817 (17) | 0.120 (6)* | 0.389 (18) |
H10A | 0.3165 | −0.2181 | 0.2545 | 0.144* | 0.389 (18) |
C11A | 0.4060 (12) | −0.2411 (5) | 0.3143 (19) | 0.120 (6)* | 0.389 (18) |
C12A | 0.4630 (12) | −0.2143 (7) | 0.3542 (19) | 0.120 (6)* | 0.389 (18) |
H12A | 0.4975 | −0.2425 | 0.3764 | 0.144* | 0.389 (18) |
C13A | 0.4696 (11) | −0.1461 (7) | 0.3615 (19) | 0.120 (6)* | 0.389 (18) |
H13A | 0.5087 | −0.1277 | 0.3888 | 0.144* | 0.389 (18) |
C14A | 0.3972 (15) | −0.3155 (9) | 0.307 (2) | 0.120 (6)* | 0.389 (18) |
H14A | 0.3573 | −0.3319 | 0.2800 | 0.144* | 0.389 (18) |
C15A | 0.4342 (8) | −0.3513 (7) | 0.3321 (10) | 0.120 (6)* | 0.389 (18) |
H15A | 0.4738 | −0.3325 | 0.3574 | 0.144* | 0.389 (18) |
N2 | 0.4338 (4) | −0.5692 (4) | 0.3437 (4) | 0.065 (2) | |
C16 | 0.3808 (5) | −0.5309 (5) | 0.2928 (5) | 0.072 (3) | |
H16 | 0.3462 | −0.5543 | 0.2629 | 0.087* | |
C17 | 0.3822 (6) | −0.4649 (5) | 0.2895 (6) | 0.076 (3) | |
H17 | 0.3481 | −0.4430 | 0.2571 | 0.091* | |
C18 | 0.4322 (6) | −0.4253 (5) | 0.3322 (6) | 0.082 (3) | |
C19 | 0.4831 (6) | −0.4584 (5) | 0.3794 (6) | 0.079 (3) | |
H19 | 0.5173 | −0.4324 | 0.4063 | 0.094* | |
C20 | 0.4862 (5) | −0.5244 (5) | 0.3887 (6) | 0.071 (3) | |
H20 | 0.5208 | −0.5435 | 0.4231 | 0.086* | |
C21 | 0.5877 (5) | 0.3271 (4) | 0.3480 (5) | 0.0508 (19) | |
C22 | 0.6548 (4) | 0.3250 (3) | 0.3920 (4) | 0.0398 (16) | |
C23 | 0.7173 (5) | 0.3269 (5) | 0.3496 (6) | 0.064 (2) | |
H23 | 0.7174 | 0.3284 | 0.2897 | 0.077* | |
C24 | 0.7785 (5) | 0.3266 (4) | 0.3919 (7) | 0.071 (3) | |
H24 | 0.8205 | 0.3278 | 0.3617 | 0.085* | |
C25 | 0.7783 (5) | 0.3245 (4) | 0.4782 (7) | 0.065 (3) | |
C26 | 0.7186 (6) | 0.3239 (4) | 0.5216 (6) | 0.073 (3) | |
H26 | 0.7192 | 0.3229 | 0.5815 | 0.088* | |
C27 | 0.6576 (5) | 0.3248 (4) | 0.4796 (5) | 0.056 (2) | |
H27 | 0.6160 | 0.3253 | 0.5109 | 0.067* | |
C28 | 0.8434 (7) | 0.3261 (5) | 0.5294 (13) | 0.104 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0365 (6) | 0.0764 (7) | 0.0360 (6) | 0.0008 (4) | 0.0013 (4) | −0.0022 (4) |
O1 | 0.040 (4) | 0.106 (5) | 0.092 (5) | 0.012 (3) | −0.009 (4) | −0.003 (4) |
O2 | 0.099 (6) | 0.118 (6) | 0.047 (4) | −0.004 (4) | −0.027 (4) | 0.013 (3) |
O3 | 0.109 (8) | 0.088 (6) | 0.168 (10) | 0.011 (4) | −0.106 (8) | −0.005 (6) |
O4 | 0.059 (6) | 0.098 (6) | 0.199 (11) | −0.006 (4) | −0.044 (6) | 0.023 (6) |
N1 | 0.056 (5) | 0.094 (6) | 0.059 (5) | 0.007 (4) | 0.004 (4) | −0.003 (4) |
C1 | 0.154 (14) | 0.093 (9) | 0.085 (9) | −0.029 (8) | −0.008 (9) | −0.016 (6) |
C2 | 0.158 (15) | 0.103 (11) | 0.111 (11) | −0.019 (9) | 0.004 (10) | −0.033 (8) |
C3 | 0.24 (2) | 0.076 (10) | 0.18 (2) | 0.007 (12) | 0.087 (16) | −0.003 (11) |
C4 | 0.173 (17) | 0.090 (10) | 0.163 (16) | −0.001 (10) | −0.045 (13) | 0.004 (9) |
C5 | 0.098 (10) | 0.088 (8) | 0.113 (10) | −0.002 (7) | −0.003 (8) | 0.009 (7) |
N2 | 0.073 (6) | 0.084 (5) | 0.038 (4) | 0.003 (4) | 0.019 (4) | 0.000 (3) |
C16 | 0.090 (8) | 0.081 (7) | 0.045 (5) | 0.007 (5) | 0.019 (5) | −0.010 (4) |
C17 | 0.102 (9) | 0.067 (6) | 0.058 (6) | 0.009 (5) | 0.004 (6) | −0.002 (4) |
C18 | 0.104 (9) | 0.090 (7) | 0.051 (6) | 0.011 (7) | 0.025 (6) | 0.002 (5) |
C19 | 0.098 (9) | 0.078 (7) | 0.060 (6) | 0.001 (6) | 0.028 (6) | 0.000 (5) |
C20 | 0.074 (7) | 0.082 (7) | 0.058 (5) | 0.010 (5) | 0.014 (5) | −0.011 (5) |
C21 | 0.047 (5) | 0.054 (5) | 0.051 (5) | −0.004 (4) | −0.010 (4) | 0.002 (4) |
C22 | 0.043 (4) | 0.043 (4) | 0.033 (4) | −0.004 (3) | 0.000 (3) | 0.003 (3) |
C23 | 0.038 (5) | 0.100 (7) | 0.055 (5) | −0.006 (4) | 0.006 (4) | 0.004 (4) |
C24 | 0.046 (5) | 0.073 (6) | 0.094 (8) | 0.003 (4) | 0.005 (5) | 0.016 (5) |
C25 | 0.048 (6) | 0.056 (5) | 0.092 (8) | 0.003 (4) | −0.024 (5) | 0.006 (4) |
C26 | 0.082 (7) | 0.093 (7) | 0.045 (5) | −0.003 (6) | −0.027 (5) | −0.007 (4) |
C27 | 0.045 (5) | 0.067 (5) | 0.055 (5) | −0.002 (4) | 0.002 (4) | −0.004 (4) |
C28 | 0.058 (8) | 0.061 (6) | 0.194 (15) | −0.011 (5) | −0.083 (10) | 0.018 (8) |
Zn1—O1 | 1.966 (6) | C12—C13 | 1.3900 |
Zn1—O3i | 1.992 (8) | C14—C15 | 1.132 (19) |
Zn1—O2ii | 2.036 (6) | C15—C18 | 1.497 (15) |
Zn1—N2iii | 2.053 (8) | C8A—C9A | 1.3900 |
Zn1—N1 | 2.104 (5) | C8A—C13A | 1.3900 |
O1—C21 | 1.237 (11) | C9A—C10A | 1.3900 |
O2—C21 | 1.198 (10) | C10A—C11A | 1.3900 |
O2—Zn1ii | 2.036 (6) | C11A—C12A | 1.3900 |
O3—C28 | 1.18 (2) | C11A—C14A | 1.517 (17) |
O3—Zn1iv | 1.992 (8) | C12A—C13A | 1.3900 |
O4—C28 | 1.215 (19) | C14A—C15A | 1.10 (2) |
N1—C1 | 1.3900 | C15A—C18 | 1.497 (15) |
N1—C5 | 1.3900 | N2—C16 | 1.523 (10) |
C1—C2 | 1.3900 | N2—C20 | 1.540 (10) |
C2—C3 | 1.3900 | N2—Zn1v | 2.053 (8) |
C3—C4 | 1.3900 | C16—C17 | 1.336 (12) |
C3—C6 | 1.527 (17) | C17—C18 | 1.432 (14) |
C4—C5 | 1.3900 | C18—C19 | 1.411 (14) |
C6—C7 | 1.14 (2) | C19—C20 | 1.344 (13) |
C7—C8 | 1.509 (16) | C21—C22 | 1.482 (11) |
C7—C8A | 1.533 (16) | C22—C27 | 1.389 (11) |
C8—C9 | 1.3900 | C22—C23 | 1.392 (11) |
C8—C13 | 1.3900 | C23—C24 | 1.368 (13) |
C9—C10 | 1.3900 | C24—C25 | 1.369 (15) |
C10—C11 | 1.3900 | C25—C26 | 1.352 (14) |
C11—C12 | 1.3900 | C25—C28 | 1.506 (13) |
C11—C14 | 1.499 (16) | C26—C27 | 1.363 (13) |
O1—Zn1—O3i | 141.6 (5) | C9A—C8A—C7 | 122.2 (7) |
O1—Zn1—O2ii | 122.1 (3) | C13A—C8A—C7 | 117.8 (7) |
O3i—Zn1—O2ii | 96.2 (5) | C8A—C9A—C10A | 120.0 |
O1—Zn1—N2iii | 91.5 (3) | C11A—C10A—C9A | 120.0 |
O3i—Zn1—N2iii | 91.6 (3) | C12A—C11A—C10A | 120.0 |
O2ii—Zn1—N2iii | 88.8 (3) | C12A—C11A—C14A | 120.7 (8) |
O1—Zn1—N1 | 89.3 (3) | C10A—C11A—C14A | 119.3 (7) |
O3i—Zn1—N1 | 89.7 (3) | C13A—C12A—C11A | 120.0 |
O2ii—Zn1—N1 | 88.3 (3) | C12A—C13A—C8A | 120.0 |
N2iii—Zn1—N1 | 177.0 (2) | C15A—C14A—C11A | 123.7 (18) |
C21—O1—Zn1 | 129.8 (7) | C14A—C15A—C18 | 130.2 (17) |
C21—O2—Zn1ii | 164.4 (8) | C16—N2—C20 | 113.4 (7) |
C28—O3—Zn1iv | 110.0 (11) | C16—N2—Zn1v | 124.6 (6) |
C1—N1—C5 | 120.0 | C20—N2—Zn1v | 122.1 (6) |
C1—N1—Zn1 | 119.2 (4) | C17—C16—N2 | 120.9 (9) |
C5—N1—Zn1 | 120.8 (4) | C16—C17—C18 | 123.7 (10) |
C2—C1—N1 | 120.0 | C19—C18—C17 | 117.7 (10) |
C1—C2—C3 | 120.0 | C19—C18—C15 | 117.2 (11) |
C4—C3—C2 | 120.0 | C17—C18—C15 | 125.2 (11) |
C4—C3—C6 | 111.2 (12) | C19—C18—C15A | 117.2 (11) |
C2—C3—C6 | 128.8 (12) | C17—C18—C15A | 125.2 (11) |
C3—C4—C5 | 120.0 | C20—C19—C18 | 124.0 (11) |
C4—C5—N1 | 120.0 | C19—C20—N2 | 120.3 (9) |
C7—C6—C3 | 131 (3) | O2—C21—O1 | 122.4 (9) |
C6—C7—C8 | 131 (2) | O2—C21—C22 | 117.8 (9) |
C6—C7—C8A | 150 (2) | O1—C21—C22 | 119.8 (8) |
C9—C8—C13 | 120.0 | C27—C22—C23 | 116.6 (8) |
C9—C8—C7 | 116.8 (7) | C27—C22—C21 | 120.4 (7) |
C13—C8—C7 | 123.2 (7) | C23—C22—C21 | 122.9 (7) |
C10—C9—C8 | 120.0 | C24—C23—C22 | 121.8 (8) |
C9—C10—C11 | 120.0 | C23—C24—C25 | 119.2 (9) |
C10—C11—C12 | 120.0 | C26—C25—C24 | 120.7 (9) |
C10—C11—C14 | 119.4 (7) | C26—C25—C28 | 116.8 (12) |
C12—C11—C14 | 120.5 (7) | C24—C25—C28 | 122.4 (12) |
C11—C12—C13 | 120.0 | C25—C26—C27 | 120.1 (9) |
C12—C13—C8 | 120.0 | C26—C27—C22 | 121.6 (9) |
C15—C14—C11 | 126.1 (17) | O3—C28—O4 | 116.3 (10) |
C14—C15—C18 | 134.6 (17) | O3—C28—C25 | 121.9 (16) |
C9A—C8A—C13A | 120.0 | O4—C28—C25 | 121.8 (18) |
Symmetry codes: (i) x−1/2, y, −z+1; (ii) −x+1, y, −z+1/2; (iii) x, y+1, z; (iv) x+1/2, y, −z+1; (v) x, y−1, z. |
C56H40N4O8Zn2 | F(000) = 4224 |
Mr = 1027.66 | Dx = 1.199 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 27.5072 (12) Å | Cell parameters from 9884 reflections |
b = 29.3890 (14) Å | θ = 2.2–27.7° |
c = 14.9485 (7) Å | µ = 0.89 mm−1 |
β = 109.537 (2)° | T = 173 K |
V = 11388.7 (9) Å3 | Block, yellow |
Z = 8 | 0.70 × 0.38 × 0.20 mm |
Bruker APEX-II CCD diffractometer | 10607 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.045 |
Absorption correction: multi-scan SADABS (Sheldrick, 2014) | θmax = 28.4°, θmin = 2.0° |
Tmin = 0.601, Tmax = 0.848 | h = −36→36 |
55236 measured reflections | k = −39→38 |
14223 independent reflections | l = −19→19 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.133 | w = 1/[σ2(Fo2) + (0.0743P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = 0.001 |
14223 reflections | Δρmax = 0.63 e Å−3 |
631 parameters | Δρmin = −0.49 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Initially normal data were used to refine the structure. Due to problems in idenditifying the electron densities and refining the atoms we used squeeze program. Further all the other data in this series were squeezed. For uniformity, this data were also squeezed. |
x | y | z | Uiso*/Ueq | ||
Zn1 | 0.36217 (2) | 0.12686 (2) | 0.35512 (2) | 0.02048 (8) | |
Zn2 | 0.37649 (2) | 0.11015 (2) | 0.63940 (2) | 0.01875 (8) | |
O1 | 0.33304 (6) | 0.14731 (7) | 0.20868 (13) | 0.0385 (4) | |
O2 | 0.39216 (7) | 0.09401 (6) | 0.24723 (12) | 0.0329 (4) | |
O3 | 0.31877 (6) | 0.17322 (5) | 0.39355 (12) | 0.0266 (4) | |
O4 | 0.31991 (5) | 0.14291 (5) | 0.53128 (12) | 0.0241 (3) | |
O5 | 0.41238 (6) | 0.09576 (5) | 0.46907 (12) | 0.0290 (4) | |
O6 | 0.42133 (6) | 0.06354 (5) | 0.60787 (13) | 0.0271 (4) | |
O7 | 0.40158 (9) | 0.09983 (8) | 0.78483 (15) | 0.0511 (6) | |
O8 | 0.34472 (8) | 0.15447 (10) | 0.75038 (16) | 0.0674 (7) | |
N1 | 0.42369 (7) | 0.17652 (6) | 0.37377 (15) | 0.0260 (4) | |
C1 | 0.47128 (9) | 0.16381 (8) | 0.3797 (2) | 0.0333 (6) | |
H1 | 0.4789 | 0.1322 | 0.3836 | 0.040* | |
C2 | 0.51014 (9) | 0.19367 (9) | 0.3805 (2) | 0.0368 (6) | |
H2 | 0.5431 | 0.1826 | 0.3833 | 0.044* | |
C3 | 0.50063 (9) | 0.24001 (9) | 0.37722 (19) | 0.0348 (6) | |
C4 | 0.45182 (10) | 0.25308 (9) | 0.3744 (2) | 0.0408 (7) | |
H4 | 0.4436 | 0.2845 | 0.3735 | 0.049* | |
C5 | 0.41515 (10) | 0.22124 (8) | 0.3728 (2) | 0.0342 (6) | |
H5 | 0.3821 | 0.2315 | 0.3709 | 0.041* | |
C6 | 0.53845 (11) | 0.27479 (10) | 0.3751 (2) | 0.0439 (7) | |
H6A | 0.5293 | 0.3054 | 0.3822 | 0.053* | |
C7 | 0.58392 (10) | 0.26858 (10) | 0.3644 (2) | 0.0459 (7) | |
H7A | 0.5944 | 0.2381 | 0.3600 | 0.055* | |
C8 | 0.61944 (10) | 0.30488 (11) | 0.3587 (2) | 0.0443 (7) | |
C9 | 0.66457 (11) | 0.29549 (11) | 0.3417 (3) | 0.0727 (13) | |
H9 | 0.6731 | 0.2648 | 0.3337 | 0.087* | |
C10 | 0.69787 (11) | 0.33001 (12) | 0.3360 (3) | 0.0733 (13) | |
H10 | 0.7285 | 0.3224 | 0.3233 | 0.088* | |
C11 | 0.68747 (11) | 0.37510 (10) | 0.3484 (2) | 0.0462 (7) | |
C12 | 0.64192 (16) | 0.38415 (12) | 0.3637 (4) | 0.0780 (14) | |
H12 | 0.6330 | 0.4149 | 0.3704 | 0.094* | |
C13 | 0.60913 (15) | 0.35041 (12) | 0.3695 (3) | 0.0790 (14) | |
H13 | 0.5783 | 0.3583 | 0.3812 | 0.095* | |
C14 | 0.72338 (11) | 0.41180 (10) | 0.3432 (2) | 0.0468 (7) | |
H14 | 0.7538 | 0.4031 | 0.3309 | 0.056* | |
C15 | 0.71647 (11) | 0.45546 (10) | 0.3542 (2) | 0.0452 (7) | |
H15 | 0.6858 | 0.4635 | 0.3663 | 0.054* | |
N2 | 0.81127 (7) | 0.56947 (7) | 0.34426 (14) | 0.0261 (4) | |
C16 | 0.82737 (9) | 0.52686 (8) | 0.33915 (19) | 0.0307 (5) | |
H16 | 0.8603 | 0.5228 | 0.3328 | 0.037* | |
C17 | 0.79923 (9) | 0.48869 (9) | 0.3425 (2) | 0.0353 (6) | |
H17 | 0.8130 | 0.4593 | 0.3396 | 0.042* | |
C18 | 0.75037 (10) | 0.49317 (9) | 0.35015 (19) | 0.0362 (6) | |
C19 | 0.73360 (10) | 0.53800 (10) | 0.3552 (2) | 0.0420 (7) | |
H19 | 0.7007 | 0.5433 | 0.3609 | 0.050* | |
C20 | 0.76451 (9) | 0.57414 (9) | 0.3520 (2) | 0.0355 (6) | |
H20 | 0.7520 | 0.6040 | 0.3553 | 0.043* | |
N3 | 0.42792 (6) | 0.16464 (6) | 0.64022 (14) | 0.0213 (4) | |
C21 | 0.47581 (8) | 0.15703 (8) | 0.63891 (17) | 0.0243 (5) | |
H21 | 0.4879 | 0.1265 | 0.6444 | 0.029* | |
C22 | 0.50808 (8) | 0.19083 (8) | 0.63009 (17) | 0.0261 (5) | |
H22 | 0.5413 | 0.1835 | 0.6278 | 0.031* | |
C23 | 0.49221 (8) | 0.23587 (8) | 0.62457 (18) | 0.0287 (5) | |
C24 | 0.44270 (8) | 0.24372 (8) | 0.62699 (19) | 0.0300 (5) | |
H24 | 0.4298 | 0.2739 | 0.6227 | 0.036* | |
C25 | 0.41264 (8) | 0.20806 (8) | 0.63551 (18) | 0.0256 (5) | |
H25 | 0.3793 | 0.2144 | 0.6382 | 0.031* | |
C26 | 0.52495 (9) | 0.27387 (9) | 0.6173 (2) | 0.0352 (6) | |
H26 | 0.5090 | 0.3027 | 0.5993 | 0.042* | |
C27 | 0.57527 (9) | 0.27102 (9) | 0.6340 (2) | 0.0377 (6) | |
H27 | 0.5908 | 0.2420 | 0.6513 | 0.045* | |
C28 | 0.60936 (9) | 0.30867 (9) | 0.6281 (2) | 0.0375 (6) | |
C29 | 0.66197 (10) | 0.30145 (9) | 0.6551 (2) | 0.0446 (7) | |
H29 | 0.6755 | 0.2723 | 0.6781 | 0.053* | |
C30 | 0.69534 (10) | 0.33562 (9) | 0.6494 (2) | 0.0447 (7) | |
H30 | 0.7312 | 0.3295 | 0.6671 | 0.054* | |
C31 | 0.67706 (10) | 0.37887 (10) | 0.6182 (2) | 0.0423 (7) | |
C32 | 0.62364 (11) | 0.38644 (10) | 0.5922 (3) | 0.0520 (9) | |
H32 | 0.6103 | 0.4160 | 0.5723 | 0.062* | |
C33 | 0.59052 (10) | 0.35219 (10) | 0.5950 (3) | 0.0508 (8) | |
H33 | 0.5545 | 0.3579 | 0.5744 | 0.061* | |
C34 | 0.71308 (10) | 0.41438 (9) | 0.6139 (2) | 0.0408 (7) | |
H34 | 0.7481 | 0.4055 | 0.6283 | 0.049* | |
C35 | 0.70242 (9) | 0.45771 (9) | 0.5921 (2) | 0.0393 (7) | |
H35 | 0.6673 | 0.4669 | 0.5726 | 0.047* | |
N4 | 0.81727 (7) | 0.55927 (6) | 0.61949 (15) | 0.0258 (4) | |
C36 | 0.82726 (9) | 0.51506 (8) | 0.6118 (2) | 0.0305 (5) | |
H36 | 0.8611 | 0.5066 | 0.6150 | 0.037* | |
C37 | 0.79081 (9) | 0.48115 (8) | 0.5995 (2) | 0.0323 (6) | |
H37 | 0.7997 | 0.4503 | 0.5933 | 0.039* | |
C38 | 0.74135 (9) | 0.49230 (8) | 0.59617 (19) | 0.0298 (5) | |
C39 | 0.73097 (9) | 0.53843 (9) | 0.6023 (2) | 0.0349 (6) | |
H39 | 0.6974 | 0.5479 | 0.5988 | 0.042* | |
C40 | 0.76929 (9) | 0.57021 (9) | 0.6135 (2) | 0.0324 (6) | |
H40 | 0.7611 | 0.6014 | 0.6172 | 0.039* | |
C41 | 0.36413 (9) | 0.12113 (9) | 0.18884 (18) | 0.0285 (5) | |
C42 | 0.36743 (9) | 0.12382 (8) | 0.09027 (17) | 0.0247 (5) | |
C43 | 0.39878 (9) | 0.09375 (8) | 0.06325 (18) | 0.0284 (5) | |
H43 | 0.4187 | 0.0719 | 0.1072 | 0.034* | |
C44 | 0.34010 (9) | 0.15683 (9) | 0.02763 (19) | 0.0326 (6) | |
H44 | 0.3194 | 0.1780 | 0.0466 | 0.039* | |
C45 | 0.30855 (7) | 0.17317 (7) | 0.46960 (17) | 0.0206 (4) | |
C46 | 0.27828 (7) | 0.21343 (7) | 0.48507 (16) | 0.0198 (4) | |
C47 | 0.25822 (8) | 0.24497 (8) | 0.41405 (17) | 0.0231 (5) | |
H47 | 0.2639 | 0.2415 | 0.3551 | 0.028* | |
C48 | 0.27035 (8) | 0.21811 (7) | 0.57225 (17) | 0.0226 (5) | |
H48 | 0.2842 | 0.1965 | 0.6214 | 0.027* | |
C49 | 0.43006 (7) | 0.06596 (7) | 0.53053 (17) | 0.0208 (5) | |
C50 | 0.46643 (7) | 0.03150 (7) | 0.51475 (17) | 0.0201 (4) | |
C51 | 0.47184 (8) | 0.02826 (7) | 0.42561 (17) | 0.0218 (5) | |
H51 | 0.4527 | 0.0477 | 0.3753 | 0.026* | |
C52 | 0.49439 (8) | 0.00372 (7) | 0.58868 (17) | 0.0232 (5) | |
H52 | 0.4905 | 0.0065 | 0.6492 | 0.028* | |
C53 | 0.37308 (11) | 0.12767 (11) | 0.8070 (2) | 0.0434 (8) | |
C54 | 0.37310 (9) | 0.12799 (9) | 0.90839 (18) | 0.0307 (6) | |
C55 | 0.40116 (9) | 0.09554 (9) | 0.97197 (19) | 0.0315 (6) | |
H55 | 0.4221 | 0.0745 | 0.9531 | 0.038* | |
C56 | 0.34310 (9) | 0.15882 (9) | 0.9363 (2) | 0.0363 (6) | |
H56 | 0.3244 | 0.1815 | 0.8932 | 0.044* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.02228 (13) | 0.02142 (14) | 0.02110 (15) | 0.00133 (9) | 0.01174 (11) | −0.00148 (11) |
Zn2 | 0.02133 (12) | 0.01782 (13) | 0.02088 (15) | 0.00067 (9) | 0.01206 (11) | −0.00013 (10) |
O1 | 0.0343 (9) | 0.0550 (12) | 0.0317 (10) | −0.0019 (8) | 0.0186 (8) | −0.0105 (9) |
O2 | 0.0417 (9) | 0.0364 (10) | 0.0231 (9) | −0.0053 (8) | 0.0141 (8) | 0.0032 (8) |
O3 | 0.0329 (8) | 0.0233 (8) | 0.0310 (10) | 0.0075 (6) | 0.0203 (8) | 0.0009 (7) |
O4 | 0.0234 (7) | 0.0205 (7) | 0.0299 (9) | 0.0030 (6) | 0.0110 (7) | 0.0019 (7) |
O5 | 0.0305 (8) | 0.0249 (8) | 0.0294 (10) | 0.0082 (7) | 0.0069 (8) | −0.0005 (8) |
O6 | 0.0310 (8) | 0.0208 (8) | 0.0394 (10) | 0.0014 (6) | 0.0251 (8) | −0.0004 (8) |
O7 | 0.0788 (14) | 0.0570 (13) | 0.0314 (11) | −0.0300 (12) | 0.0369 (11) | −0.0139 (10) |
O8 | 0.0540 (13) | 0.113 (2) | 0.0343 (13) | −0.0098 (14) | 0.0136 (11) | 0.0251 (14) |
N1 | 0.0300 (9) | 0.0236 (10) | 0.0281 (11) | −0.0028 (8) | 0.0147 (9) | −0.0017 (9) |
C1 | 0.0314 (12) | 0.0238 (12) | 0.0477 (17) | −0.0012 (9) | 0.0173 (12) | 0.0001 (12) |
C2 | 0.0292 (12) | 0.0341 (14) | 0.0487 (18) | −0.0055 (10) | 0.0151 (12) | −0.0005 (13) |
C3 | 0.0395 (13) | 0.0348 (14) | 0.0336 (15) | −0.0116 (11) | 0.0167 (12) | −0.0038 (12) |
C4 | 0.0514 (15) | 0.0246 (12) | 0.0559 (19) | −0.0056 (11) | 0.0307 (15) | −0.0015 (13) |
C5 | 0.0374 (12) | 0.0267 (12) | 0.0461 (17) | 0.0009 (10) | 0.0240 (13) | 0.0004 (12) |
C6 | 0.0515 (16) | 0.0348 (15) | 0.0520 (19) | −0.0179 (12) | 0.0260 (15) | −0.0038 (14) |
C7 | 0.0452 (15) | 0.0436 (16) | 0.0444 (18) | −0.0193 (13) | 0.0092 (14) | 0.0055 (14) |
C8 | 0.0439 (15) | 0.0463 (17) | 0.0412 (17) | −0.0192 (13) | 0.0121 (14) | 0.0052 (14) |
C9 | 0.0379 (15) | 0.0436 (18) | 0.132 (4) | −0.0048 (13) | 0.022 (2) | 0.021 (2) |
C10 | 0.0346 (15) | 0.052 (2) | 0.131 (4) | −0.0090 (14) | 0.024 (2) | 0.019 (2) |
C11 | 0.0457 (15) | 0.0441 (16) | 0.0452 (18) | −0.0219 (13) | 0.0105 (14) | 0.0006 (15) |
C12 | 0.091 (3) | 0.0450 (19) | 0.130 (4) | −0.0337 (19) | 0.079 (3) | −0.024 (2) |
C13 | 0.086 (3) | 0.055 (2) | 0.128 (4) | −0.0330 (19) | 0.078 (3) | −0.029 (2) |
C14 | 0.0378 (14) | 0.0485 (18) | 0.0518 (19) | −0.0172 (13) | 0.0118 (14) | 0.0053 (16) |
C15 | 0.0466 (15) | 0.0466 (17) | 0.0486 (19) | −0.0228 (13) | 0.0241 (15) | −0.0071 (15) |
N2 | 0.0279 (9) | 0.0268 (10) | 0.0257 (11) | −0.0052 (8) | 0.0116 (9) | −0.0026 (9) |
C16 | 0.0264 (11) | 0.0323 (13) | 0.0349 (15) | −0.0053 (9) | 0.0124 (11) | −0.0031 (12) |
C17 | 0.0344 (12) | 0.0305 (13) | 0.0398 (16) | −0.0057 (10) | 0.0108 (12) | 0.0004 (12) |
C18 | 0.0394 (13) | 0.0411 (15) | 0.0306 (14) | −0.0157 (11) | 0.0149 (12) | −0.0047 (13) |
C19 | 0.0343 (13) | 0.0471 (16) | 0.0520 (19) | −0.0122 (12) | 0.0244 (14) | −0.0116 (15) |
C20 | 0.0313 (12) | 0.0384 (14) | 0.0409 (16) | −0.0060 (10) | 0.0177 (12) | −0.0081 (13) |
N3 | 0.0215 (8) | 0.0225 (9) | 0.0202 (10) | −0.0012 (7) | 0.0074 (8) | −0.0003 (8) |
C21 | 0.0233 (10) | 0.0227 (11) | 0.0255 (12) | −0.0020 (8) | 0.0065 (10) | −0.0041 (10) |
C22 | 0.0223 (10) | 0.0297 (12) | 0.0265 (13) | −0.0028 (9) | 0.0087 (10) | −0.0022 (11) |
C23 | 0.0259 (11) | 0.0320 (12) | 0.0275 (13) | −0.0080 (9) | 0.0080 (10) | 0.0001 (11) |
C24 | 0.0283 (11) | 0.0222 (11) | 0.0385 (15) | −0.0015 (9) | 0.0098 (11) | 0.0007 (11) |
C25 | 0.0227 (10) | 0.0248 (11) | 0.0296 (13) | −0.0011 (9) | 0.0091 (10) | 0.0001 (10) |
C26 | 0.0350 (12) | 0.0283 (13) | 0.0438 (16) | −0.0064 (10) | 0.0150 (12) | 0.0057 (12) |
C27 | 0.0345 (12) | 0.0323 (13) | 0.0461 (17) | −0.0093 (11) | 0.0134 (13) | 0.0054 (13) |
C28 | 0.0305 (12) | 0.0330 (13) | 0.0470 (17) | −0.0091 (10) | 0.0102 (12) | 0.0081 (13) |
C29 | 0.0326 (13) | 0.0313 (14) | 0.068 (2) | −0.0043 (11) | 0.0152 (14) | 0.0094 (15) |
C30 | 0.0299 (12) | 0.0371 (15) | 0.065 (2) | −0.0057 (11) | 0.0130 (14) | 0.0101 (15) |
C31 | 0.0356 (13) | 0.0384 (15) | 0.0525 (19) | −0.0124 (11) | 0.0139 (14) | 0.0052 (14) |
C32 | 0.0344 (14) | 0.0370 (15) | 0.083 (3) | −0.0041 (11) | 0.0171 (16) | 0.0187 (17) |
C33 | 0.0286 (12) | 0.0478 (17) | 0.076 (2) | −0.0034 (12) | 0.0177 (15) | 0.0181 (17) |
C34 | 0.0306 (12) | 0.0405 (15) | 0.0497 (18) | −0.0095 (11) | 0.0114 (13) | 0.0088 (14) |
C35 | 0.0297 (12) | 0.0349 (14) | 0.0548 (19) | −0.0079 (11) | 0.0159 (13) | 0.0055 (14) |
N4 | 0.0248 (9) | 0.0221 (9) | 0.0337 (12) | 0.0006 (7) | 0.0140 (9) | 0.0036 (9) |
C36 | 0.0297 (11) | 0.0246 (12) | 0.0413 (15) | −0.0017 (9) | 0.0172 (12) | 0.0020 (11) |
C37 | 0.0321 (12) | 0.0234 (11) | 0.0450 (16) | −0.0010 (9) | 0.0178 (12) | 0.0034 (12) |
C38 | 0.0292 (11) | 0.0294 (12) | 0.0320 (14) | −0.0064 (9) | 0.0118 (11) | 0.0053 (11) |
C39 | 0.0237 (11) | 0.0346 (13) | 0.0490 (17) | −0.0006 (10) | 0.0156 (12) | 0.0094 (13) |
C40 | 0.0296 (11) | 0.0290 (12) | 0.0451 (16) | 0.0027 (9) | 0.0213 (12) | 0.0055 (12) |
C41 | 0.0300 (11) | 0.0356 (13) | 0.0239 (13) | −0.0115 (10) | 0.0143 (11) | −0.0076 (11) |
C42 | 0.0276 (11) | 0.0284 (12) | 0.0221 (12) | −0.0047 (9) | 0.0135 (10) | −0.0013 (10) |
C43 | 0.0364 (12) | 0.0258 (12) | 0.0257 (13) | 0.0002 (10) | 0.0141 (11) | 0.0020 (11) |
C44 | 0.0312 (12) | 0.0357 (14) | 0.0339 (15) | 0.0034 (10) | 0.0149 (11) | −0.0003 (12) |
C45 | 0.0179 (9) | 0.0186 (10) | 0.0257 (12) | 0.0013 (8) | 0.0078 (9) | −0.0011 (10) |
C46 | 0.0191 (9) | 0.0200 (10) | 0.0220 (11) | 0.0013 (8) | 0.0091 (9) | −0.0008 (9) |
C47 | 0.0257 (10) | 0.0263 (11) | 0.0201 (12) | 0.0053 (9) | 0.0116 (9) | −0.0002 (10) |
C48 | 0.0261 (10) | 0.0223 (11) | 0.0217 (12) | 0.0043 (8) | 0.0110 (10) | 0.0031 (10) |
C49 | 0.0163 (9) | 0.0183 (10) | 0.0285 (12) | −0.0028 (8) | 0.0084 (9) | −0.0060 (10) |
C50 | 0.0190 (9) | 0.0177 (10) | 0.0268 (12) | −0.0008 (8) | 0.0117 (9) | −0.0027 (10) |
C51 | 0.0243 (10) | 0.0204 (10) | 0.0227 (12) | 0.0041 (8) | 0.0105 (9) | 0.0028 (10) |
C52 | 0.0287 (11) | 0.0232 (11) | 0.0235 (12) | 0.0014 (9) | 0.0163 (10) | 0.0001 (10) |
C53 | 0.0447 (15) | 0.066 (2) | 0.0187 (13) | −0.0306 (14) | 0.0094 (12) | 0.0055 (14) |
C54 | 0.0337 (12) | 0.0390 (14) | 0.0221 (13) | −0.0138 (10) | 0.0128 (11) | −0.0015 (11) |
C55 | 0.0369 (12) | 0.0336 (13) | 0.0296 (14) | −0.0043 (10) | 0.0187 (12) | −0.0038 (12) |
C56 | 0.0347 (12) | 0.0419 (15) | 0.0300 (14) | 0.0013 (11) | 0.0076 (12) | 0.0127 (13) |
Zn1—O3 | 2.0175 (15) | C19—C20 | 1.371 (3) |
Zn1—O5 | 2.0176 (17) | N3—C25 | 1.338 (3) |
Zn1—O1 | 2.150 (2) | N3—C21 | 1.343 (3) |
Zn1—N2i | 2.1631 (18) | C21—C22 | 1.368 (3) |
Zn1—N1 | 2.1810 (18) | C22—C23 | 1.387 (3) |
Zn1—O2 | 2.2590 (17) | C23—C24 | 1.394 (3) |
Zn1—C41 | 2.510 (3) | C23—C26 | 1.461 (3) |
Zn2—O6 | 2.0022 (15) | C24—C25 | 1.367 (3) |
Zn2—O4 | 2.0686 (16) | C26—C27 | 1.325 (3) |
Zn2—O7 | 2.071 (2) | C27—C28 | 1.472 (3) |
Zn2—N3 | 2.1342 (17) | C28—C29 | 1.382 (3) |
Zn2—N4i | 2.1572 (18) | C28—C33 | 1.406 (4) |
Zn2—O8 | 2.487 (3) | C29—C30 | 1.382 (3) |
Zn2—C53 | 2.590 (3) | C30—C31 | 1.389 (4) |
O1—C41 | 1.257 (3) | C31—C32 | 1.406 (4) |
O2—C41 | 1.242 (3) | C31—C34 | 1.455 (3) |
O3—C45 | 1.259 (3) | C32—C33 | 1.368 (4) |
O4—C45 | 1.243 (3) | C34—C35 | 1.323 (4) |
O5—C49 | 1.245 (3) | C35—C38 | 1.463 (3) |
O6—C49 | 1.259 (3) | N4—C40 | 1.332 (3) |
O7—C53 | 1.252 (4) | N4—C36 | 1.341 (3) |
O8—C53 | 1.226 (4) | N4—Zn2ii | 2.1571 (18) |
N1—C5 | 1.334 (3) | C36—C37 | 1.382 (3) |
N1—C1 | 1.336 (3) | C37—C38 | 1.384 (3) |
C1—C2 | 1.380 (3) | C38—C39 | 1.395 (3) |
C2—C3 | 1.385 (4) | C39—C40 | 1.376 (3) |
C3—C4 | 1.383 (3) | C41—C42 | 1.508 (3) |
C3—C6 | 1.467 (3) | C42—C44 | 1.383 (3) |
C4—C5 | 1.370 (3) | C42—C43 | 1.386 (3) |
C6—C7 | 1.325 (4) | C43—C55iii | 1.389 (3) |
C7—C8 | 1.468 (4) | C44—C56iii | 1.396 (4) |
C8—C9 | 1.376 (4) | C45—C46 | 1.508 (3) |
C8—C13 | 1.388 (5) | C46—C47 | 1.378 (3) |
C9—C10 | 1.388 (4) | C46—C48 | 1.398 (3) |
C10—C11 | 1.381 (5) | C47—C48iv | 1.395 (3) |
C11—C12 | 1.373 (5) | C48—C47iv | 1.394 (3) |
C11—C14 | 1.482 (4) | C49—C50 | 1.497 (3) |
C12—C13 | 1.362 (4) | C50—C52 | 1.382 (3) |
C14—C15 | 1.316 (4) | C50—C51 | 1.393 (3) |
C15—C18 | 1.463 (3) | C51—C52v | 1.387 (3) |
N2—C20 | 1.336 (3) | C52—C51v | 1.387 (3) |
N2—C16 | 1.339 (3) | C53—C54 | 1.516 (4) |
N2—Zn1ii | 2.1630 (18) | C54—C56 | 1.381 (4) |
C16—C17 | 1.373 (3) | C54—C55 | 1.385 (4) |
C17—C18 | 1.393 (3) | C55—C43vi | 1.389 (3) |
C18—C19 | 1.406 (4) | C56—C44vi | 1.396 (4) |
O3—Zn1—O5 | 111.64 (7) | C16—C17—C18 | 119.8 (2) |
O3—Zn1—O1 | 92.66 (7) | C17—C18—C19 | 115.8 (2) |
O5—Zn1—O1 | 154.57 (7) | C17—C18—C15 | 125.3 (3) |
O3—Zn1—N2i | 96.78 (7) | C19—C18—C15 | 118.9 (2) |
O5—Zn1—N2i | 87.33 (7) | C20—C19—C18 | 120.3 (2) |
O1—Zn1—N2i | 97.47 (7) | N2—C20—C19 | 123.3 (2) |
O3—Zn1—N1 | 91.11 (7) | C25—N3—C21 | 116.78 (19) |
O5—Zn1—N1 | 84.97 (7) | C25—N3—Zn2 | 121.29 (14) |
O1—Zn1—N1 | 87.25 (7) | C21—N3—Zn2 | 121.78 (15) |
N2i—Zn1—N1 | 170.58 (7) | N3—C21—C22 | 123.5 (2) |
O3—Zn1—O2 | 152.13 (7) | C21—C22—C23 | 119.8 (2) |
O5—Zn1—O2 | 95.67 (7) | C22—C23—C24 | 116.5 (2) |
O1—Zn1—O2 | 59.56 (7) | C22—C23—C26 | 123.0 (2) |
N2i—Zn1—O2 | 89.71 (7) | C24—C23—C26 | 120.5 (2) |
N1—Zn1—O2 | 85.66 (7) | C25—C24—C23 | 120.1 (2) |
O3—Zn1—C41 | 122.54 (8) | N3—C25—C24 | 123.2 (2) |
O5—Zn1—C41 | 124.78 (8) | C27—C26—C23 | 124.7 (2) |
O1—Zn1—C41 | 30.06 (7) | C26—C27—C28 | 126.0 (3) |
N2i—Zn1—C41 | 95.81 (7) | C29—C28—C33 | 118.0 (2) |
N1—Zn1—C41 | 84.19 (7) | C29—C28—C27 | 119.5 (2) |
O2—Zn1—C41 | 29.59 (7) | C33—C28—C27 | 122.5 (2) |
O6—Zn2—O4 | 119.75 (7) | C30—C29—C28 | 121.5 (3) |
O6—Zn2—O7 | 97.56 (9) | C29—C30—C31 | 120.8 (2) |
O4—Zn2—O7 | 141.97 (8) | C30—C31—C32 | 117.7 (2) |
O6—Zn2—N3 | 93.17 (6) | C30—C31—C34 | 119.7 (2) |
O4—Zn2—N3 | 88.81 (6) | C32—C31—C34 | 122.6 (3) |
O7—Zn2—N3 | 96.68 (7) | C33—C32—C31 | 121.3 (3) |
O6—Zn2—N4i | 89.40 (7) | C32—C33—C28 | 120.6 (2) |
O4—Zn2—N4i | 83.04 (7) | C35—C34—C31 | 127.1 (3) |
O7—Zn2—N4i | 90.83 (8) | C34—C35—C38 | 124.0 (2) |
N3—Zn2—N4i | 171.67 (7) | C40—N4—C36 | 117.1 (2) |
O6—Zn2—O8 | 153.78 (8) | C40—N4—Zn2ii | 121.85 (16) |
O4—Zn2—O8 | 86.39 (7) | C36—N4—Zn2ii | 121.09 (14) |
O7—Zn2—O8 | 56.26 (8) | N4—C36—C37 | 123.4 (2) |
N3—Zn2—O8 | 89.04 (7) | C36—C37—C38 | 119.6 (2) |
N4i—Zn2—O8 | 92.15 (7) | C37—C38—C39 | 116.6 (2) |
O6—Zn2—C53 | 126.03 (10) | C37—C38—C35 | 122.3 (2) |
O4—Zn2—C53 | 113.71 (9) | C39—C38—C35 | 121.0 (2) |
O7—Zn2—C53 | 28.49 (9) | C40—C39—C38 | 120.2 (2) |
N3—Zn2—C53 | 94.80 (8) | N4—C40—C39 | 123.1 (2) |
N4i—Zn2—C53 | 90.07 (8) | O2—C41—O1 | 122.6 (2) |
O8—Zn2—C53 | 27.86 (9) | O2—C41—C42 | 119.6 (2) |
C41—O1—Zn1 | 91.02 (16) | O1—C41—C42 | 117.8 (2) |
C41—O2—Zn1 | 86.47 (14) | O2—C41—Zn1 | 63.94 (13) |
C45—O3—Zn1 | 126.04 (14) | O1—C41—Zn1 | 58.92 (13) |
C45—O4—Zn2 | 148.13 (14) | C42—C41—Zn1 | 172.85 (17) |
C49—O5—Zn1 | 158.45 (15) | C44—C42—C43 | 120.0 (2) |
C49—O6—Zn2 | 119.95 (14) | C44—C42—C41 | 120.1 (2) |
C53—O7—Zn2 | 99.41 (19) | C43—C42—C41 | 119.9 (2) |
C53—O8—Zn2 | 80.8 (2) | C42—C43—C55iii | 120.0 (2) |
C5—N1—C1 | 116.2 (2) | C42—C44—C56iii | 119.7 (2) |
C5—N1—Zn1 | 122.11 (15) | O4—C45—O3 | 126.4 (2) |
C1—N1—Zn1 | 121.51 (16) | O4—C45—C46 | 117.5 (2) |
N1—C1—C2 | 124.2 (2) | O3—C45—C46 | 116.03 (19) |
C1—C2—C3 | 119.3 (2) | C47—C46—C48 | 120.32 (19) |
C4—C3—C2 | 116.4 (2) | C47—C46—C45 | 120.6 (2) |
C4—C3—C6 | 119.6 (2) | C48—C46—C45 | 119.1 (2) |
C2—C3—C6 | 124.0 (2) | C46—C47—C48iv | 120.7 (2) |
C5—C4—C3 | 120.8 (2) | C47iv—C48—C46 | 119.0 (2) |
N1—C5—C4 | 123.1 (2) | O5—C49—O6 | 124.77 (19) |
C7—C6—C3 | 127.7 (3) | O5—C49—C50 | 118.5 (2) |
C6—C7—C8 | 125.4 (3) | O6—C49—C50 | 116.7 (2) |
C9—C8—C13 | 116.5 (3) | C52—C50—C51 | 121.04 (19) |
C9—C8—C7 | 121.6 (3) | C52—C50—C49 | 119.7 (2) |
C13—C8—C7 | 121.9 (3) | C51—C50—C49 | 119.2 (2) |
C8—C9—C10 | 121.3 (3) | C52v—C51—C50 | 119.0 (2) |
C11—C10—C9 | 121.5 (3) | C50—C52—C51v | 120.0 (2) |
C12—C11—C10 | 116.7 (3) | O8—C53—O7 | 123.2 (3) |
C12—C11—C14 | 121.9 (3) | O8—C53—C54 | 118.3 (3) |
C10—C11—C14 | 121.3 (3) | O7—C53—C54 | 118.5 (3) |
C13—C12—C11 | 122.0 (3) | O8—C53—Zn2 | 71.39 (18) |
C12—C13—C8 | 121.9 (3) | O7—C53—Zn2 | 52.10 (15) |
C15—C14—C11 | 125.2 (3) | C54—C53—Zn2 | 168.7 (2) |
C14—C15—C18 | 127.8 (3) | C56—C54—C55 | 119.8 (2) |
C20—N2—C16 | 116.6 (2) | C56—C54—C53 | 120.4 (3) |
C20—N2—Zn1ii | 122.08 (17) | C55—C54—C53 | 119.7 (2) |
C16—N2—Zn1ii | 121.01 (15) | C54—C55—C43vi | 120.1 (2) |
N2—C16—C17 | 124.1 (2) | C54—C56—C44vi | 120.3 (2) |
Symmetry codes: (i) x−1/2, y−1/2, z; (ii) x+1/2, y+1/2, z; (iii) x, y, z−1; (iv) −x+1/2, −y+1/2, −z+1; (v) −x+1, −y, −z+1; (vi) x, y, z+1. |
C56H40N4O8Zn2 | Dx = 1.125 Mg m−3 |
Mr = 1027.66 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pcca | Cell parameters from 9984 reflections |
a = 20.030 (3) Å | θ = 2.3–27.3° |
b = 20.005 (3) Å | µ = 0.84 mm−1 |
c = 15.145 (2) Å | T = 173 K |
V = 6068.8 (14) Å3 | Block, red |
Z = 4 | 0.46 × 0.41 × 0.30 mm |
F(000) = 2112 |
Bruker APEX-II CCD diffractometer | 3975 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.074 |
Absorption correction: multi-scan SADABS (Sheldrick, 2011) | θmax = 26.0°, θmin = 2.0° |
Tmin = 0.703, Tmax = 0.801 | h = −24→24 |
46693 measured reflections | k = −24→24 |
5979 independent reflections | l = −18→18 |
Refinement on F2 | 440 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.073 | H-atom parameters constrained |
wR(F2) = 0.231 | w = 1/[σ2(Fo2) + (0.1154P)2 + 7.2582P] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max = 0.001 |
5979 reflections | Δρmax = 0.91 e Å−3 |
294 parameters | Δρmin = −0.72 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Crystallized in the orthorhombic space group Pcca with Z = 4. The asymmetric unit contains half of the formula unit. The dimer formed by dimerization of trans,cis,trans-bpeb disordered due to crystallographic centre of inversion. Due to this disorder soft constraints (FLAT, SAME, SADI) were used to retain the geometry of molecule. Only isotropic thermal parameter could be refined for these bpeb-dimer fragment. Again one DMF was disordered by crystallographic inversion centre. The rest of the electron densities were too complicated to resolve. Hence they were assigned as O atoms of water molecules. They could as well be highly disordered DMF.[Zn2(bdc)2(dimer)].DMF.6.5H2O. For uniformity, the referee suggested to squeeze the data and hence squeezed. The agreement factors of the squeezed better than the unsqueezed data. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Zn1 | 0.43270 (3) | 0.66969 (2) | 0.85781 (3) | 0.0250 (2) | |
O1 | 0.52593 (15) | 0.67007 (14) | 0.9065 (2) | 0.0355 (8) | |
O2 | 0.57615 (18) | 0.67078 (17) | 0.7764 (2) | 0.0449 (9) | |
O3 | 0.8303 (2) | 0.67234 (15) | 1.1227 (3) | 0.0521 (11) | |
O4 | 0.8841 (2) | 0.67063 (16) | 0.9961 (3) | 0.0565 (11) | |
N1 | 0.4379 (6) | 0.5644 (5) | 0.8558 (8) | 0.024 (4)* | 0.5 |
C1 | 0.4867 (6) | 0.5310 (5) | 0.8977 (8) | 0.034 (4)* | 0.5 |
H1 | 0.5149 | 0.5556 | 0.9363 | 0.041* | 0.5 |
C2 | 0.4988 (5) | 0.4633 (4) | 0.8886 (7) | 0.029 (3)* | 0.5 |
H2A | 0.5336 | 0.4426 | 0.9212 | 0.035* | 0.5 |
C3 | 0.4601 (5) | 0.4260 (4) | 0.8318 (7) | 0.024 (2)* | 0.5 |
C4 | 0.4064 (6) | 0.4579 (4) | 0.7932 (7) | 0.030 (3)* | 0.5 |
H4 | 0.3767 | 0.4339 | 0.7560 | 0.037* | 0.5 |
C5 | 0.3963 (6) | 0.5258 (5) | 0.8095 (9) | 0.033 (4)* | 0.5 |
H5 | 0.3571 | 0.5459 | 0.7861 | 0.039* | 0.5 |
C6 | 0.4863 (5) | 0.3575 (4) | 0.8109 (6) | 0.033 (2)* | 0.5 |
H6 | 0.5062 | 0.3358 | 0.8642 | 0.040* | 0.5 |
C7 | 0.4391 (5) | 0.3084 (5) | 0.7602 (6) | 0.043 (2)* | 0.5 |
H7 | 0.3970 | 0.3321 | 0.7435 | 0.052* | 0.5 |
C8 | 0.4224 (5) | 0.2409 (5) | 0.8006 (7) | 0.051 (3)* | 0.5 |
C9 | 0.4677 (6) | 0.2060 (4) | 0.8435 (6) | 0.041 (2)* | 0.5 |
H9 | 0.5039 | 0.2299 | 0.8690 | 0.049* | 0.5 |
C10 | 0.4669 (6) | 0.1379 (5) | 0.8546 (7) | 0.059 (3)* | 0.5 |
H10 | 0.4991 | 0.1165 | 0.8909 | 0.071* | 0.5 |
C11 | 0.4195 (7) | 0.1021 (6) | 0.8128 (10) | 0.079 (4)* | 0.5 |
C12 | 0.3664 (7) | 0.1385 (5) | 0.7824 (9) | 0.073 (4)* | 0.5 |
H12 | 0.3265 | 0.1159 | 0.7664 | 0.087* | 0.5 |
C13 | 0.3694 (7) | 0.2077 (5) | 0.7745 (9) | 0.079 (4)* | 0.5 |
H13 | 0.3327 | 0.2312 | 0.7498 | 0.095* | 0.5 |
C14 | 0.4371 (8) | 0.0329 (8) | 0.7736 (10) | 0.108 (6)* | 0.5 |
H14 | 0.3942 | 0.0089 | 0.7618 | 0.129* | 0.5 |
C15 | 0.4872 (8) | −0.0191 (7) | 0.8174 (10) | 0.103 (6)* | 0.5 |
H15 | 0.5116 | 0.0024 | 0.8676 | 0.123* | 0.5 |
N2 | 0.4371 (5) | −0.2216 (4) | 0.8662 (7) | 0.027 (3)* | 0.5 |
C16 | 0.3959 (6) | −0.1848 (5) | 0.8195 (8) | 0.045 (3)* | 0.5 |
H16 | 0.3607 | −0.2070 | 0.7893 | 0.054* | 0.5 |
C17 | 0.4001 (7) | −0.1157 (6) | 0.8108 (11) | 0.084 (5)* | 0.5 |
H17 | 0.3668 | −0.0909 | 0.7804 | 0.101* | 0.5 |
C18 | 0.4543 (6) | −0.0853 (5) | 0.8480 (9) | 0.058 (4)* | 0.5 |
C19 | 0.4928 (6) | −0.1198 (5) | 0.9043 (9) | 0.058 (4)* | 0.5 |
H19 | 0.5261 | −0.0978 | 0.9383 | 0.070* | 0.5 |
C20 | 0.4830 (6) | −0.1884 (5) | 0.9119 (9) | 0.041 (3)* | 0.5 |
H20 | 0.5105 | −0.2127 | 0.9516 | 0.050* | 0.5 |
N3 | 0.5710 (6) | 0.5599 (6) | 0.6504 (8) | 0.031 (5)* | 0.5 |
C21 | 0.5219 (6) | 0.5235 (5) | 0.6137 (8) | 0.038 (5)* | 0.5 |
H21 | 0.4923 | 0.5442 | 0.5731 | 0.046* | 0.5 |
C22 | 0.5134 (6) | 0.4561 (5) | 0.6339 (8) | 0.040 (3)* | 0.5 |
H22 | 0.4785 | 0.4316 | 0.6063 | 0.048* | 0.5 |
C23 | 0.5551 (5) | 0.4247 (4) | 0.6936 (7) | 0.033 (3)* | 0.5 |
C24 | 0.6073 (6) | 0.4620 (5) | 0.7256 (8) | 0.036 (3)* | 0.5 |
H24 | 0.6403 | 0.4414 | 0.7615 | 0.043* | 0.5 |
C25 | 0.6122 (6) | 0.5296 (5) | 0.7058 (8) | 0.026 (3)* | 0.5 |
H25 | 0.6465 | 0.5551 | 0.7331 | 0.031* | 0.5 |
C26 | 0.5369 (5) | 0.3566 (4) | 0.7298 (6) | 0.038 (2)* | 0.5 |
H26 | 0.5784 | 0.3321 | 0.7471 | 0.045* | 0.5 |
C27 | 0.4897 (5) | 0.3085 (5) | 0.6782 (6) | 0.049 (3)* | 0.5 |
H27 | 0.4694 | 0.3320 | 0.6265 | 0.059* | 0.5 |
C28 | 0.5137 (7) | 0.2388 (6) | 0.6514 (9) | 0.073 (4)* | 0.5 |
C29 | 0.5648 (8) | 0.2054 (7) | 0.6847 (12) | 0.099 (6)* | 0.5 |
H29 | 0.6006 | 0.2289 | 0.7118 | 0.119* | 0.5 |
C30 | 0.5661 (9) | 0.1352 (8) | 0.6801 (15) | 0.126 (8)* | 0.5 |
H30 | 0.6059 | 0.1125 | 0.6963 | 0.151* | 0.5 |
C31 | 0.5126 (9) | 0.0986 (7) | 0.6532 (12) | 0.106 (6)* | 0.5 |
C32 | 0.4692 (10) | 0.1341 (8) | 0.6038 (14) | 0.139 (7)* | 0.5 |
H32 | 0.4394 | 0.1115 | 0.5653 | 0.166* | 0.5 |
C33 | 0.4680 (8) | 0.2029 (7) | 0.6086 (11) | 0.102 (5)* | 0.5 |
H33 | 0.4326 | 0.2260 | 0.5799 | 0.122* | 0.5 |
C34 | 0.4806 (8) | 0.0313 (7) | 0.6838 (9) | 0.094 (5)* | 0.5 |
H34 | 0.4560 | 0.0088 | 0.6347 | 0.113* | 0.5 |
C35 | 0.5328 (8) | −0.0178 (7) | 0.7296 (10) | 0.107 (6)* | 0.5 |
H35 | 0.5749 | 0.0074 | 0.7423 | 0.129* | 0.5 |
N4 | 0.5664 (5) | −0.2225 (5) | 0.6544 (7) | 0.036 (3)* | 0.5 |
C36 | 0.6065 (5) | −0.1894 (5) | 0.7073 (8) | 0.039 (3)* | 0.5 |
H36 | 0.6414 | −0.2130 | 0.7361 | 0.047* | 0.5 |
C37 | 0.5999 (6) | −0.1224 (5) | 0.7227 (9) | 0.054 (3)* | 0.5 |
H37 | 0.6314 | −0.1010 | 0.7600 | 0.065* | 0.5 |
C38 | 0.5507 (7) | −0.0856 (6) | 0.6874 (10) | 0.071 (4)* | 0.5 |
C39 | 0.5090 (7) | −0.1163 (6) | 0.6309 (10) | 0.063 (4)* | 0.5 |
H39 | 0.4745 | −0.0925 | 0.6015 | 0.076* | 0.5 |
C40 | 0.5186 (7) | −0.1851 (5) | 0.6172 (9) | 0.052 (4)* | 0.5 |
H40 | 0.4886 | −0.2070 | 0.5782 | 0.062* | 0.5 |
C41 | 0.5766 (2) | 0.67179 (19) | 0.8582 (3) | 0.0286 (11) | |
C42 | 0.6429 (2) | 0.67537 (18) | 0.9037 (3) | 0.0260 (9) | |
C43 | 0.6469 (3) | 0.6791 (2) | 0.9952 (3) | 0.0380 (11) | |
H43 | 0.6069 | 0.6816 | 1.0289 | 0.046* | |
C44 | 0.7073 (3) | 0.6794 (2) | 1.0380 (3) | 0.0410 (12) | |
H44 | 0.7088 | 0.6828 | 1.1005 | 0.049* | |
C45 | 0.7657 (2) | 0.67477 (19) | 0.9908 (4) | 0.0361 (11) | |
C46 | 0.7626 (2) | 0.6705 (2) | 0.8997 (3) | 0.0361 (11) | |
H46 | 0.8027 | 0.6667 | 0.8666 | 0.043* | |
C47 | 0.7017 (3) | 0.6716 (2) | 0.8560 (3) | 0.0353 (11) | |
H47 | 0.7004 | 0.6697 | 0.7933 | 0.042* | |
C48 | 0.8319 (3) | 0.6726 (2) | 1.0396 (4) | 0.0469 (14) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0203 (3) | 0.0253 (3) | 0.0296 (3) | 0.0000 (2) | 0.0023 (2) | 0.00168 (18) |
O1 | 0.0140 (16) | 0.0446 (18) | 0.048 (2) | −0.0013 (13) | 0.0009 (16) | 0.0029 (14) |
O2 | 0.037 (2) | 0.067 (2) | 0.0299 (17) | 0.0076 (17) | −0.0089 (16) | −0.0097 (15) |
O3 | 0.054 (3) | 0.0392 (19) | 0.063 (2) | 0.0023 (17) | −0.033 (2) | 0.0006 (16) |
O4 | 0.029 (2) | 0.046 (2) | 0.094 (3) | 0.0004 (16) | −0.024 (2) | 0.0005 (19) |
C41 | 0.023 (3) | 0.027 (2) | 0.036 (3) | 0.0016 (18) | −0.008 (2) | −0.0027 (18) |
C42 | 0.018 (2) | 0.025 (2) | 0.035 (2) | −0.0003 (17) | −0.0058 (19) | −0.0030 (17) |
C43 | 0.025 (3) | 0.051 (3) | 0.038 (3) | 0.005 (2) | 0.003 (2) | −0.004 (2) |
C44 | 0.035 (3) | 0.047 (3) | 0.041 (3) | 0.007 (2) | −0.015 (2) | −0.003 (2) |
C45 | 0.024 (3) | 0.027 (2) | 0.057 (3) | −0.0028 (19) | −0.014 (2) | 0.003 (2) |
C46 | 0.023 (3) | 0.033 (2) | 0.053 (3) | 0.0020 (19) | 0.003 (2) | 0.000 (2) |
C47 | 0.026 (3) | 0.048 (3) | 0.032 (2) | −0.004 (2) | 0.000 (2) | 0.000 (2) |
C48 | 0.031 (3) | 0.023 (2) | 0.086 (4) | −0.001 (2) | −0.020 (3) | 0.001 (2) |
Zn1—O1 | 2.008 (3) | C16—C17 | 1.391 (11) |
Zn1—O2i | 2.040 (3) | C17—C18 | 1.366 (12) |
Zn1—O3ii | 2.073 (4) | C18—C19 | 1.341 (12) |
Zn1—N1 | 2.110 (10) | C19—C20 | 1.391 (10) |
Zn1—O4ii | 2.418 (4) | N3—C25 | 1.324 (11) |
Zn1—C48ii | 2.548 (6) | N3—C21 | 1.344 (11) |
O1—C41 | 1.253 (6) | C21—C22 | 1.392 (11) |
O2—C41 | 1.239 (5) | C22—C23 | 1.384 (11) |
O2—Zn1i | 2.040 (3) | C23—C24 | 1.372 (11) |
O3—C48 | 1.259 (7) | C23—C26 | 1.513 (10) |
O3—Zn1iii | 2.073 (4) | C24—C25 | 1.389 (10) |
O4—C48 | 1.237 (7) | C26—C27 | 1.559 (11) |
O4—Zn1iii | 2.418 (4) | C27—C28 | 1.530 (12) |
N1—C5 | 1.336 (11) | C28—C29 | 1.322 (12) |
N1—C1 | 1.344 (11) | C28—C33 | 1.332 (12) |
C1—C2 | 1.382 (10) | C29—C30 | 1.407 (13) |
C2—C3 | 1.378 (11) | C30—C31 | 1.360 (13) |
C3—C4 | 1.381 (11) | C31—C32 | 1.348 (13) |
C3—C6 | 1.501 (9) | C31—C34 | 1.562 (13) |
C4—C5 | 1.395 (10) | C32—C33 | 1.380 (13) |
C6—C7 | 1.565 (11) | C34—C35 | 1.593 (13) |
C6—C26 | 1.591 (10) | C35—C38 | 1.543 (13) |
C7—C8 | 1.521 (11) | N4—C36 | 1.313 (11) |
C7—C27 | 1.603 (11) | N4—C40 | 1.340 (11) |
C8—C13 | 1.313 (11) | C36—C37 | 1.367 (10) |
C8—C9 | 1.316 (11) | C37—C38 | 1.341 (12) |
C9—C10 | 1.373 (11) | C38—C39 | 1.343 (12) |
C10—C11 | 1.347 (12) | C39—C40 | 1.406 (11) |
C11—C12 | 1.369 (12) | C41—C42 | 1.497 (6) |
C11—C14 | 1.547 (13) | C42—C47 | 1.384 (7) |
C12—C13 | 1.391 (12) | C42—C43 | 1.390 (6) |
C14—C15 | 1.590 (14) | C43—C44 | 1.373 (7) |
C14—C34 | 1.615 (13) | C44—C45 | 1.374 (8) |
C15—C18 | 1.552 (13) | C45—C46 | 1.383 (7) |
C15—C35 | 1.613 (13) | C45—C48 | 1.518 (7) |
N2—C16 | 1.313 (11) | C46—C47 | 1.389 (7) |
N2—C20 | 1.328 (10) | C48—Zn1iii | 2.548 (6) |
O1—Zn1—O2i | 116.53 (14) | N2—C20—C19 | 123.2 (10) |
O1—Zn1—O3ii | 150.21 (16) | C25—N3—C21 | 117.9 (11) |
O2i—Zn1—O3ii | 93.19 (16) | N3—C21—C22 | 121.7 (11) |
O1—Zn1—N1 | 87.9 (3) | C23—C22—C21 | 120.6 (10) |
O2i—Zn1—N1 | 90.0 (3) | C24—C23—C22 | 116.4 (8) |
O3ii—Zn1—N1 | 94.4 (3) | C24—C23—C26 | 123.1 (9) |
O1—Zn1—O4ii | 92.18 (15) | C22—C23—C26 | 120.0 (9) |
O2i—Zn1—O4ii | 151.26 (15) | C23—C24—C25 | 120.5 (10) |
O3ii—Zn1—O4ii | 58.07 (16) | N3—C25—C24 | 122.6 (11) |
N1—Zn1—O4ii | 92.4 (3) | C23—C26—C27 | 121.3 (9) |
O1—Zn1—C48ii | 120.85 (18) | C23—C26—C6 | 115.0 (8) |
O2i—Zn1—C48ii | 122.58 (19) | C27—C26—C6 | 90.5 (6) |
O3ii—Zn1—C48ii | 29.39 (18) | C28—C27—C26 | 120.3 (9) |
N1—Zn1—C48ii | 94.1 (4) | C28—C27—C7 | 113.8 (9) |
O4ii—Zn1—C48ii | 28.68 (17) | C26—C27—C7 | 89.8 (5) |
C41—O1—Zn1 | 122.7 (3) | C29—C28—C33 | 116.5 (12) |
C41—O2—Zn1i | 175.5 (4) | C29—C28—C27 | 127.0 (12) |
C48—O3—Zn1iii | 96.7 (4) | C33—C28—C27 | 113.9 (11) |
C48—O4—Zn1iii | 81.5 (4) | C28—C29—C30 | 119.9 (14) |
C5—N1—C1 | 114.5 (10) | C31—C30—C29 | 122.5 (15) |
C5—N1—Zn1 | 123.7 (8) | C32—C31—C30 | 113.0 (14) |
C1—N1—Zn1 | 121.7 (8) | C32—C31—C34 | 110.8 (14) |
N1—C1—C2 | 124.5 (11) | C30—C31—C34 | 134.3 (15) |
C3—C2—C1 | 119.7 (9) | C31—C32—C33 | 120.5 (14) |
C2—C3—C4 | 116.8 (7) | C28—C33—C32 | 123.4 (13) |
C2—C3—C6 | 115.4 (8) | C31—C34—C35 | 113.0 (13) |
C4—C3—C6 | 127.3 (9) | C31—C34—C14 | 117.0 (14) |
C3—C4—C5 | 119.3 (9) | C35—C34—C14 | 90.0 (6) |
N1—C5—C4 | 124.4 (11) | C38—C35—C34 | 120.9 (14) |
C3—C6—C7 | 117.6 (9) | C38—C35—C15 | 117.3 (14) |
C3—C6—C26 | 113.3 (8) | C34—C35—C15 | 89.8 (6) |
C7—C6—C26 | 90.0 (6) | C36—N4—C40 | 114.4 (10) |
C8—C7—C6 | 119.5 (8) | N4—C36—C37 | 122.6 (10) |
C8—C7—C27 | 116.9 (8) | C38—C37—C36 | 122.8 (11) |
C6—C7—C27 | 89.8 (5) | C37—C38—C39 | 117.4 (10) |
C13—C8—C9 | 116.0 (10) | C37—C38—C35 | 119.2 (11) |
C13—C8—C7 | 120.3 (9) | C39—C38—C35 | 121.4 (12) |
C9—C8—C7 | 121.2 (9) | C38—C39—C40 | 117.1 (11) |
C8—C9—C10 | 125.3 (10) | N4—C40—C39 | 125.6 (12) |
C11—C10—C9 | 118.6 (11) | O2—C41—O1 | 125.3 (4) |
C10—C11—C12 | 115.0 (11) | O2—C41—C42 | 117.9 (4) |
C10—C11—C14 | 119.7 (12) | O1—C41—C42 | 116.8 (4) |
C12—C11—C14 | 121.6 (11) | C47—C42—C43 | 118.3 (4) |
C11—C12—C13 | 121.7 (11) | C47—C42—C41 | 120.7 (4) |
C8—C13—C12 | 120.8 (11) | C43—C42—C41 | 120.9 (4) |
C11—C14—C15 | 124.7 (13) | C44—C43—C42 | 121.4 (5) |
C11—C14—C34 | 117.6 (14) | C43—C44—C45 | 120.3 (4) |
C15—C14—C34 | 89.9 (6) | C44—C45—C46 | 118.9 (4) |
C18—C15—C14 | 114.4 (14) | C44—C45—C48 | 119.5 (5) |
C18—C15—C35 | 120.1 (14) | C46—C45—C48 | 121.6 (5) |
C14—C15—C35 | 90.2 (7) | C45—C46—C47 | 121.0 (5) |
C16—N2—C20 | 115.8 (9) | C42—C47—C46 | 119.9 (4) |
N2—C16—C17 | 124.8 (11) | O4—C48—O3 | 123.7 (5) |
C18—C17—C16 | 116.8 (12) | O4—C48—C45 | 118.6 (6) |
C19—C18—C17 | 119.4 (10) | O3—C48—C45 | 117.7 (5) |
C19—C18—C15 | 112.6 (11) | O4—C48—Zn1iii | 69.8 (3) |
C17—C18—C15 | 126.5 (12) | O3—C48—Zn1iii | 53.9 (3) |
C18—C19—C20 | 118.6 (10) | C45—C48—Zn1iii | 171.6 (5) |
Symmetry codes: (i) −x+1, y, −z+3/2; (ii) x−1/2, y, −z+2; (iii) x+1/2, y, −z+2. |
C56H40N4O8Zn2 | Dx = 1.152 Mg m−3 |
Mr = 1027.66 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pcca | Cell parameters from 9896 reflections |
a = 20.0663 (6) Å | θ = 2.3–26.4° |
b = 19.9342 (7) Å | µ = 0.86 mm−1 |
c = 14.8166 (5) Å | T = 173 K |
V = 5926.7 (3) Å3 | Plate, yellow |
Z = 4 | 0.14 × 0.10 × 0.07 mm |
F(000) = 2112 |
Bruker APEX-II CCD diffractometer | 3043 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.119 |
Absorption correction: multi-scan SADABS (Sheldrick, 2012) | θmax = 26.0°, θmin = 2.0° |
Tmin = 0.888, Tmax = 0.965 | h = −24→24 |
64566 measured reflections | k = −23→22 |
5651 independent reflections | l = −17→18 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.109 | w = 1/[σ2(Fo2) + (0.1667P)2 + 25.0974P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.347 | (Δ/σ)max < 0.001 |
S = 1.03 | Δρmax = 0.90 e Å−3 |
5651 reflections | Δρmin = −0.62 e Å−3 |
295 parameters | Extinction correction: SHELXL-2014/7 (Sheldrick 2014, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
440 restraints | Extinction coefficient: 0.00009 (12) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Zn1 | 0.43536 (4) | 0.66393 (5) | 0.86152 (6) | 0.0481 (4) | |
O1 | 0.5286 (3) | 0.6667 (3) | 0.9082 (4) | 0.0653 (16) | |
O2 | 0.5750 (3) | 0.6654 (5) | 0.7752 (5) | 0.100 (3) | |
O3 | 0.8356 (3) | 0.6657 (4) | 1.1149 (6) | 0.091 (2) | |
O4 | 0.8874 (3) | 0.6652 (3) | 0.9852 (6) | 0.091 (2) | |
N1 | 0.4377 (9) | 0.5542 (8) | 0.8686 (13) | 0.060 (8)* | 0.5 |
C1 | 0.4903 (8) | 0.5237 (8) | 0.8992 (12) | 0.047 (6)* | 0.5 |
H1 | 0.5208 | 0.5502 | 0.9328 | 0.056* | 0.5 |
C2 | 0.5065 (10) | 0.4579 (8) | 0.8883 (14) | 0.073 (7)* | 0.5 |
H2A | 0.5464 | 0.4401 | 0.9130 | 0.088* | 0.5 |
C3 | 0.4633 (8) | 0.4183 (8) | 0.8405 (13) | 0.058 (5)* | 0.5 |
C4 | 0.4056 (9) | 0.4478 (9) | 0.8074 (13) | 0.060 (5)* | 0.5 |
H4 | 0.3730 | 0.4228 | 0.7752 | 0.072* | 0.5 |
C5 | 0.3984 (13) | 0.5148 (10) | 0.824 (2) | 0.126 (15)* | 0.5 |
H5 | 0.3596 | 0.5352 | 0.7992 | 0.151* | 0.5 |
C6 | 0.4903 (11) | 0.3506 (9) | 0.8117 (15) | 0.088 (7)* | 0.5 |
H6 | 0.5095 | 0.3269 | 0.8652 | 0.106* | 0.5 |
C7 | 0.4416 (12) | 0.2991 (14) | 0.7553 (18) | 0.142 (12)* | 0.5 |
H7 | 0.4006 | 0.3217 | 0.7319 | 0.171* | 0.5 |
C8 | 0.4260 (15) | 0.2328 (11) | 0.8054 (19) | 0.110 (9)* | 0.5 |
C9 | 0.4636 (15) | 0.1945 (16) | 0.855 (2) | 0.19 (2)* | 0.5 |
H9 | 0.4968 | 0.2180 | 0.8883 | 0.226* | 0.5 |
C10 | 0.4637 (16) | 0.1265 (16) | 0.869 (2) | 0.128 (10)* | 0.5 |
H10 | 0.4936 | 0.1045 | 0.9088 | 0.154* | 0.5 |
C11 | 0.416 (3) | 0.0931 (17) | 0.819 (4) | 0.42 (7)* | 0.5 |
C12 | 0.3713 (19) | 0.1313 (19) | 0.770 (3) | 0.215 (19)* | 0.5 |
H12 | 0.3343 | 0.1106 | 0.7411 | 0.258* | 0.5 |
C13 | 0.3807 (18) | 0.1989 (18) | 0.763 (3) | 0.25 (2)* | 0.5 |
H13 | 0.3516 | 0.2231 | 0.7244 | 0.299* | 0.5 |
C14 | 0.451 (4) | 0.050 (3) | 0.747 (5) | 0.52 (8)* | 0.5 |
H14 | 0.4085 | 0.0352 | 0.7188 | 0.618* | 0.5 |
C15 | 0.458 (4) | −0.020 (2) | 0.808 (4) | 0.26 (3)* | 0.5 |
H15 | 0.4845 | −0.0005 | 0.8590 | 0.314* | 0.5 |
N2 | 0.4366 (7) | −0.2265 (7) | 0.8650 (10) | 0.041 (4)* | 0.5 |
C16 | 0.3878 (11) | −0.1918 (13) | 0.8316 (19) | 0.119 (12)* | 0.5 |
H16 | 0.3500 | −0.2163 | 0.8116 | 0.143* | 0.5 |
C17 | 0.3850 (17) | −0.1233 (15) | 0.822 (3) | 0.27 (3)* | 0.5 |
H17 | 0.3475 | −0.1019 | 0.7957 | 0.326* | 0.5 |
C18 | 0.4389 (17) | −0.0869 (14) | 0.853 (3) | 0.20 (3)* | 0.5 |
C19 | 0.4937 (11) | −0.1221 (9) | 0.8850 (15) | 0.087 (7)* | 0.5 |
H19 | 0.5348 | −0.1005 | 0.8983 | 0.104* | 0.5 |
C20 | 0.4851 (10) | −0.1898 (9) | 0.8966 (16) | 0.080 (8)* | 0.5 |
H20 | 0.5179 | −0.2124 | 0.9313 | 0.097* | 0.5 |
N3 | 0.5640 (7) | 0.5577 (7) | 0.6508 (12) | 0.037 (5)* | 0.5 |
C21 | 0.5187 (10) | 0.5165 (8) | 0.6206 (13) | 0.075 (9)* | 0.5 |
H21 | 0.4849 | 0.5362 | 0.5844 | 0.090* | 0.5 |
C22 | 0.5132 (10) | 0.4491 (8) | 0.6335 (14) | 0.062 (5)* | 0.5 |
H22 | 0.4799 | 0.4232 | 0.6041 | 0.074* | 0.5 |
C23 | 0.5588 (9) | 0.4204 (8) | 0.6920 (14) | 0.072 (6)* | 0.5 |
C24 | 0.6110 (9) | 0.4600 (8) | 0.7212 (14) | 0.066 (6)* | 0.5 |
H24 | 0.6454 | 0.4426 | 0.7585 | 0.079* | 0.5 |
C25 | 0.6107 (7) | 0.5249 (7) | 0.6940 (12) | 0.037 (4)* | 0.5 |
H25 | 0.6496 | 0.5500 | 0.7081 | 0.044* | 0.5 |
C26 | 0.5450 (13) | 0.3504 (11) | 0.7280 (17) | 0.121 (9)* | 0.5 |
H26 | 0.5878 | 0.3304 | 0.7500 | 0.145* | 0.5 |
C27 | 0.5011 (14) | 0.2916 (14) | 0.676 (2) | 0.156 (12)* | 0.5 |
H27 | 0.4837 | 0.3103 | 0.6184 | 0.187* | 0.5 |
C28 | 0.5338 (18) | 0.2218 (14) | 0.657 (2) | 0.128 (12)* | 0.5 |
C29 | 0.5796 (18) | 0.1781 (18) | 0.679 (3) | 0.72 (15)* | 0.5 |
H29 | 0.6191 | 0.1958 | 0.7049 | 0.865* | 0.5 |
C30 | 0.578 (2) | 0.1098 (16) | 0.668 (3) | 0.164 (18)* | 0.5 |
H30 | 0.6144 | 0.0820 | 0.6831 | 0.196* | 0.5 |
C31 | 0.519 (3) | 0.0840 (19) | 0.635 (4) | 0.27 (3)* | 0.5 |
C32 | 0.470 (2) | 0.127 (3) | 0.605 (4) | 0.30 (3)* | 0.5 |
H32 | 0.4303 | 0.1115 | 0.5771 | 0.362* | 0.5 |
C33 | 0.4824 (19) | 0.194 (2) | 0.618 (3) | 0.25 (3)* | 0.5 |
H33 | 0.4495 | 0.2238 | 0.5956 | 0.303* | 0.5 |
C34 | 0.497 (4) | 0.014 (2) | 0.667 (3) | 0.33 (4)* | 0.5 |
H34 | 0.4679 | −0.0081 | 0.6206 | 0.396* | 0.5 |
C35 | 0.522 (5) | −0.042 (3) | 0.743 (4) | 0.81 (12)* | 0.5 |
H35 | 0.5636 | −0.0236 | 0.7715 | 0.972* | 0.5 |
N4 | 0.5694 (18) | −0.2312 (15) | 0.646 (2) | 0.17 (2)* | 0.5 |
C36 | 0.6030 (12) | −0.1964 (12) | 0.7042 (19) | 0.103 (9)* | 0.5 |
H36 | 0.6366 | −0.2192 | 0.7373 | 0.124* | 0.5 |
C37 | 0.5941 (13) | −0.1292 (12) | 0.7226 (19) | 0.120 (9)* | 0.5 |
H37 | 0.6206 | −0.1066 | 0.7663 | 0.144* | 0.5 |
C38 | 0.5452 (15) | −0.0963 (12) | 0.675 (2) | 0.111 (11)* | 0.5 |
C39 | 0.508 (3) | −0.131 (2) | 0.612 (5) | 0.55 (9)* | 0.5 |
H39 | 0.4730 | −0.1103 | 0.5785 | 0.662* | 0.5 |
C40 | 0.524 (2) | −0.197 (2) | 0.603 (4) | 0.28 (4)* | 0.5 |
H40 | 0.4985 | −0.2214 | 0.5599 | 0.333* | 0.5 |
C41 | 0.5789 (4) | 0.6670 (4) | 0.8546 (6) | 0.054 (2) | |
C42 | 0.6448 (3) | 0.6686 (4) | 0.8998 (6) | 0.049 (2) | |
C43 | 0.6503 (4) | 0.6678 (5) | 0.9920 (6) | 0.073 (3) | |
H43 | 0.6111 | 0.6666 | 1.0278 | 0.087* | |
C44 | 0.7115 (5) | 0.6686 (6) | 1.0335 (7) | 0.088 (3) | |
H44 | 0.7142 | 0.6706 | 1.0975 | 0.106* | |
C45 | 0.7696 (4) | 0.6667 (4) | 0.9821 (7) | 0.062 (2) | |
C46 | 0.7647 (4) | 0.6670 (4) | 0.8914 (7) | 0.059 (2) | |
H46 | 0.8040 | 0.6676 | 0.8556 | 0.070* | |
C47 | 0.7020 (4) | 0.6667 (5) | 0.8497 (6) | 0.066 (3) | |
H47 | 0.6992 | 0.6651 | 0.7858 | 0.079* | |
C48 | 0.8366 (5) | 0.6644 (5) | 1.0297 (9) | 0.078 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0239 (5) | 0.0662 (7) | 0.0543 (6) | −0.0003 (4) | 0.0028 (4) | 0.0026 (5) |
O1 | 0.027 (3) | 0.091 (5) | 0.078 (4) | −0.005 (3) | −0.004 (3) | 0.000 (3) |
O2 | 0.057 (4) | 0.184 (9) | 0.058 (4) | 0.007 (4) | −0.018 (3) | −0.030 (5) |
O3 | 0.053 (4) | 0.112 (6) | 0.107 (6) | 0.008 (4) | −0.039 (4) | −0.014 (5) |
O4 | 0.038 (4) | 0.096 (5) | 0.140 (7) | −0.006 (3) | −0.014 (4) | 0.005 (5) |
C41 | 0.040 (4) | 0.061 (6) | 0.060 (6) | 0.001 (4) | −0.011 (4) | −0.012 (5) |
C42 | 0.029 (4) | 0.057 (5) | 0.062 (5) | 0.002 (4) | −0.003 (3) | −0.003 (4) |
C43 | 0.036 (4) | 0.129 (9) | 0.054 (5) | 0.010 (5) | −0.002 (4) | 0.009 (6) |
C44 | 0.045 (5) | 0.154 (11) | 0.065 (6) | 0.000 (6) | −0.015 (5) | 0.005 (6) |
C45 | 0.032 (4) | 0.070 (6) | 0.085 (7) | 0.004 (4) | −0.010 (4) | 0.001 (5) |
C46 | 0.027 (4) | 0.061 (6) | 0.089 (7) | 0.004 (4) | 0.012 (4) | −0.008 (5) |
C47 | 0.037 (4) | 0.093 (7) | 0.067 (6) | −0.006 (4) | −0.004 (4) | −0.014 (5) |
C48 | 0.038 (5) | 0.067 (7) | 0.129 (10) | −0.019 (5) | −0.020 (6) | −0.005 (7) |
Zn1—O1 | 1.996 (5) | C16—C17 | 1.373 (17) |
Zn1—O3i | 2.033 (7) | C17—C18 | 1.380 (18) |
Zn1—O2ii | 2.036 (7) | C18—C19 | 1.387 (17) |
Zn1—N1 | 2.189 (16) | C19—C20 | 1.372 (16) |
Zn1—O4i | 2.466 (8) | N3—C21 | 1.305 (14) |
Zn1—C48i | 2.555 (11) | N3—C25 | 1.309 (12) |
O1—C41 | 1.283 (10) | C21—C22 | 1.362 (15) |
O2—C41 | 1.180 (10) | C22—C23 | 1.384 (16) |
O2—Zn1ii | 2.036 (7) | C23—C24 | 1.382 (16) |
O3—C48 | 1.263 (13) | C23—C26 | 1.520 (19) |
O3—Zn1iii | 2.033 (7) | C24—C25 | 1.355 (14) |
O4—C48 | 1.214 (13) | C26—C27 | 1.65 (2) |
O4—Zn1iii | 2.466 (8) | C27—C28 | 1.57 (2) |
N1—C5 | 1.298 (14) | C28—C29 | 1.306 (16) |
N1—C1 | 1.299 (13) | C28—C33 | 1.308 (16) |
C1—C2 | 1.360 (14) | C29—C30 | 1.370 (17) |
C2—C3 | 1.370 (16) | C30—C31 | 1.377 (18) |
C3—C4 | 1.389 (16) | C31—C32 | 1.378 (18) |
C3—C6 | 1.514 (18) | C31—C34 | 1.54 (2) |
C4—C5 | 1.365 (15) | C32—C33 | 1.367 (17) |
C6—C7 | 1.64 (2) | C34—C35 | 1.66 (2) |
C6—C26 | 1.66 (2) | C35—C38 | 1.54 (2) |
C7—C8 | 1.55 (2) | N4—C36 | 1.301 (15) |
C7—C27 | 1.68 (2) | N4—C40 | 1.303 (16) |
C8—C13 | 1.295 (16) | C36—C37 | 1.379 (16) |
C8—C9 | 1.302 (16) | C37—C38 | 1.377 (17) |
C9—C10 | 1.370 (17) | C38—C39 | 1.379 (18) |
C10—C11 | 1.384 (18) | C39—C40 | 1.365 (17) |
C11—C12 | 1.381 (18) | C41—C42 | 1.484 (11) |
C11—C14 | 1.54 (2) | C42—C47 | 1.367 (11) |
C12—C13 | 1.365 (17) | C42—C43 | 1.370 (11) |
C14—C15 | 1.66 (2) | C43—C44 | 1.373 (13) |
C14—C34 | 1.67 (2) | C44—C45 | 1.393 (13) |
C15—C18 | 1.55 (2) | C45—C46 | 1.348 (12) |
C15—C35 | 1.67 (2) | C45—C48 | 1.518 (12) |
N2—C16 | 1.298 (15) | C46—C47 | 1.402 (11) |
N2—C20 | 1.303 (14) | C48—Zn1iii | 2.555 (10) |
O1—Zn1—O3i | 149.7 (3) | N2—C20—C19 | 127.0 (16) |
O1—Zn1—O2ii | 116.1 (3) | C21—N3—C25 | 110.6 (14) |
O3i—Zn1—O2ii | 94.0 (3) | N3—C21—C22 | 129.1 (17) |
O1—Zn1—N1 | 89.5 (5) | C21—C22—C23 | 116.2 (15) |
O3i—Zn1—N1 | 91.8 (5) | C24—C23—C22 | 117.5 (14) |
O2ii—Zn1—N1 | 93.7 (6) | C24—C23—C26 | 123.5 (16) |
O1—Zn1—O4i | 92.7 (3) | C22—C23—C26 | 118.6 (18) |
O3i—Zn1—O4i | 57.1 (3) | C25—C24—C23 | 116.6 (15) |
O2ii—Zn1—O4i | 151.1 (3) | N3—C25—C24 | 128.7 (15) |
N1—Zn1—O4i | 88.6 (5) | C23—C26—C27 | 126 (2) |
O1—Zn1—C48i | 120.6 (3) | C23—C26—C6 | 112 (2) |
O3i—Zn1—C48i | 29.2 (3) | C27—C26—C6 | 89.6 (7) |
O2ii—Zn1—C48i | 123.2 (4) | C28—C27—C26 | 119 (3) |
N1—Zn1—C48i | 89.4 (6) | C28—C27—C7 | 120 (3) |
O4i—Zn1—C48i | 27.9 (3) | C26—C27—C7 | 89.7 (7) |
C41—O1—Zn1 | 121.5 (6) | C29—C28—C33 | 112 (2) |
C41—O2—Zn1ii | 177.8 (7) | C29—C28—C27 | 147 (3) |
C48—O3—Zn1iii | 99.0 (7) | C33—C28—C27 | 97 (3) |
C48—O4—Zn1iii | 80.1 (7) | C28—C29—C30 | 128 (2) |
C5—N1—C1 | 112.9 (16) | C29—C30—C31 | 116 (2) |
C5—N1—Zn1 | 124.5 (14) | C30—C31—C32 | 119 (2) |
C1—N1—Zn1 | 120.2 (12) | C30—C31—C34 | 118 (5) |
N1—C1—C2 | 127.2 (17) | C32—C31—C34 | 118 (5) |
C1—C2—C3 | 117.8 (16) | C33—C32—C31 | 116 (2) |
C2—C3—C4 | 117.7 (14) | C28—C33—C32 | 128 (2) |
C2—C3—C6 | 115.7 (15) | C31—C34—C35 | 137 (6) |
C4—C3—C6 | 125.2 (16) | C31—C34—C14 | 89 (4) |
C5—C4—C3 | 116.1 (15) | C35—C34—C14 | 88.6 (10) |
N1—C5—C4 | 128.2 (19) | C38—C35—C34 | 97 (4) |
C3—C6—C7 | 119 (2) | C38—C35—C15 | 142 (8) |
C3—C6—C26 | 116.7 (18) | C34—C35—C15 | 88.7 (10) |
C7—C6—C26 | 90.6 (7) | C36—N4—C40 | 114 (2) |
C8—C7—C6 | 114 (2) | N4—C36—C37 | 125.8 (19) |
C8—C7—C27 | 114 (3) | C38—C37—C36 | 117.0 (17) |
C6—C7—C27 | 89.3 (7) | C37—C38—C39 | 120 (2) |
C13—C8—C9 | 112 (2) | C37—C38—C35 | 102 (3) |
C13—C8—C7 | 111 (3) | C39—C38—C35 | 129 (5) |
C9—C8—C7 | 131 (3) | C40—C39—C38 | 115 (2) |
C8—C9—C10 | 132 (2) | N4—C40—C39 | 129 (2) |
C9—C10—C11 | 113.4 (19) | O2—C41—O1 | 124.4 (8) |
C12—C11—C10 | 118 (2) | O2—C41—C42 | 120.7 (8) |
C12—C11—C14 | 104 (4) | O1—C41—C42 | 114.9 (8) |
C10—C11—C14 | 109 (5) | C47—C42—C43 | 118.3 (7) |
C13—C12—C11 | 120 (2) | C47—C42—C41 | 120.1 (8) |
C8—C13—C12 | 125 (2) | C43—C42—C41 | 121.5 (8) |
C11—C14—C15 | 97 (4) | C42—C43—C44 | 121.2 (9) |
C11—C14—C34 | 171 (6) | C43—C44—C45 | 120.2 (9) |
C15—C14—C34 | 88.8 (10) | C46—C45—C44 | 118.9 (8) |
C18—C15—C14 | 160 (6) | C46—C45—C48 | 121.8 (9) |
C18—C15—C35 | 102 (5) | C44—C45—C48 | 119.3 (9) |
C14—C15—C35 | 88.5 (10) | C45—C46—C47 | 120.3 (8) |
C16—N2—C20 | 113.7 (16) | C42—C47—C46 | 120.9 (8) |
N2—C16—C17 | 126.8 (19) | O4—C48—O3 | 123.7 (10) |
C16—C17—C18 | 117 (2) | O4—C48—C45 | 119.5 (11) |
C17—C18—C19 | 118 (2) | O3—C48—C45 | 116.7 (10) |
C17—C18—C15 | 121 (4) | O4—C48—Zn1iii | 72.0 (6) |
C19—C18—C15 | 113 (4) | O3—C48—Zn1iii | 51.8 (5) |
C20—C19—C18 | 116.1 (17) | C45—C48—Zn1iii | 168.4 (9) |
Symmetry codes: (i) x−1/2, y, −z+2; (ii) −x+1, y, −z+3/2; (iii) x+1/2, y, −z+2. |
C56H40N4O8Zn2 | F(000) = 4224 |
Mr = 1027.66 | Dx = 1.192 Mg m−3 |
Monoclinic, C2/c | Mo Kαlpha radiation, λ = 0.71073 Å |
a = 27.430 (2) Å | Cell parameters from 5473 reflections |
b = 29.305 (2) Å | θ = 2.2–28.3° |
c = 14.9087 (11) Å | µ = 0.89 mm−1 |
β = 107.070 (5)° | T = 173 K |
V = 11456.2 (16) Å3 | Plate, yellow |
Z = 8 | 0.45 × 0.13 × 0.08 mm |
Bruker APEX-II CCD diffractometer | 6657 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.092 |
Absorption correction: multi-scan SADABS (Sheldrick, 2011) | θmax = 26.5°, θmin = 1.4° |
Tmin = 0.702, Tmax = 0.937 | h = −30→34 |
50356 measured reflections | k = −36→32 |
11878 independent reflections | l = −18→18 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.086 | w = 1/[σ2(Fo2) + (0.1042P)2 + 43.8779P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.238 | (Δ/σ)max < 0.001 |
S = 1.03 | Δρmax = 0.73 e Å−3 |
11878 reflections | Δρmin = −0.71 e Å−3 |
605 parameters | Extinction correction: SHELXL-2014/7 (Sheldrick 2014, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
85 restraints | Extinction coefficient: 0.00013 (5) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Initially refinement was attempted with normal data with R(int) = 0.1078. Due to high agreement factors and problem in completing satisfactory refinements of the structural model, SQUEEZEd data was used. The refinement is marred by the disorder created by the partial dimerization. Only one of the two olefin bonds was found to form cyclobutane ring. The dimerized fragment (C8a - C40a) was included in the refinement. A common occupancy factor was refined to 0.610 (6). Only isotropic thermal parameters were refined for these "disordered" fragments, as anisotropic refinement failed. Even though the geometry of the rings were confined to hexagon using FLAT, SADI and SAME options they were not strictly maintained in some cases. However, the agreement factors are better than the unsqueezed data and hence reported here. Although the bond distances and angles are not very accurate for a detailed comparison, partial single dimerization photoreaction is proved beyond any doubt. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Zn1 | 0.35888 (3) | 0.11982 (3) | 0.36020 (5) | 0.0497 (3) | |
Zn2 | 0.38071 (3) | 0.11393 (2) | 0.64715 (5) | 0.0352 (2) | |
O1 | 0.40609 (17) | 0.09055 (16) | 0.4745 (3) | 0.0568 (13) | |
O2 | 0.42725 (15) | 0.06664 (13) | 0.6188 (3) | 0.0417 (10) | |
O3 | 0.31447 (17) | 0.16602 (15) | 0.3973 (3) | 0.0527 (12) | |
O4 | 0.32509 (16) | 0.14580 (14) | 0.5441 (3) | 0.0455 (10) | |
O5 | 0.33097 (19) | 0.13939 (18) | 0.2168 (3) | 0.0649 (14) | |
O6 | 0.39190 (18) | 0.08752 (16) | 0.2499 (3) | 0.0569 (12) | |
O7 | 0.3465 (2) | 0.1621 (3) | 0.7626 (4) | 0.096 (2) | |
O8 | 0.4033 (2) | 0.10638 (19) | 0.7890 (3) | 0.0759 (17) | |
N1 | 0.4192 (2) | 0.17021 (19) | 0.3738 (4) | 0.0543 (15) | |
C1 | 0.4678 (3) | 0.1593 (3) | 0.3806 (5) | 0.0586 (18) | |
H1 | 0.4763 | 0.1278 | 0.3848 | 0.070* | |
C2 | 0.5052 (3) | 0.1885 (3) | 0.3819 (5) | 0.069 (2) | |
H2 | 0.5384 | 0.1774 | 0.3861 | 0.083* | |
C3 | 0.4961 (4) | 0.2347 (3) | 0.3771 (6) | 0.077 (2) | |
C4 | 0.4484 (4) | 0.2469 (3) | 0.3765 (7) | 0.099 (3) | |
H4 | 0.4407 | 0.2783 | 0.3798 | 0.118* | |
C5 | 0.4104 (4) | 0.2150 (3) | 0.3712 (6) | 0.079 (2) | |
H5 | 0.3768 | 0.2255 | 0.3656 | 0.095* | |
C6 | 0.5330 (4) | 0.2700 (4) | 0.3732 (8) | 0.114 (4) | |
H6 | 0.5234 | 0.3007 | 0.3800 | 0.137* | |
C7 | 0.5794 (4) | 0.2635 (4) | 0.3608 (7) | 0.107 (3) | |
H7 | 0.5896 | 0.2330 | 0.3537 | 0.128* | |
C8 | 0.6158 (5) | 0.3008 (4) | 0.3575 (6) | 0.055 (3)* | 0.610 (6) |
C9 | 0.6619 (7) | 0.2899 (7) | 0.3382 (13) | 0.115 (6)* | 0.610 (6) |
H9 | 0.6707 | 0.2593 | 0.3292 | 0.138* | 0.610 (6) |
C10 | 0.6954 (8) | 0.3277 (7) | 0.3325 (15) | 0.145 (8)* | 0.610 (6) |
H10 | 0.7244 | 0.3219 | 0.3115 | 0.174* | 0.610 (6) |
C11 | 0.6862 (6) | 0.3734 (6) | 0.3575 (13) | 0.094 (5)* | 0.610 (6) |
C12 | 0.6356 (6) | 0.3813 (5) | 0.3608 (11) | 0.083 (5)* | 0.610 (6) |
H12 | 0.6235 | 0.4119 | 0.3534 | 0.100* | 0.610 (6) |
C13 | 0.6003 (10) | 0.3457 (8) | 0.3747 (19) | 0.186 (13)* | 0.610 (6) |
H13 | 0.5707 | 0.3519 | 0.3931 | 0.224* | 0.610 (6) |
C14 | 0.7212 (7) | 0.4077 (6) | 0.3465 (12) | 0.101 (5)* | 0.610 (6) |
H14 | 0.7520 | 0.3985 | 0.3348 | 0.122* | 0.610 (6) |
C15 | 0.7120 (7) | 0.4524 (6) | 0.3522 (11) | 0.115 (6)* | 0.610 (6) |
H15 | 0.6794 | 0.4606 | 0.3572 | 0.138* | 0.610 (6) |
N2 | 0.8119 (4) | 0.5678 (4) | 0.3481 (6) | 0.049 (3)* | 0.610 (6) |
C16 | 0.8284 (6) | 0.5229 (4) | 0.3546 (8) | 0.062 (4)* | 0.610 (6) |
H16 | 0.8633 | 0.5175 | 0.3606 | 0.075* | 0.610 (6) |
C17 | 0.7979 (5) | 0.4855 (5) | 0.3529 (8) | 0.068 (4)* | 0.610 (6) |
H17 | 0.8116 | 0.4557 | 0.3527 | 0.082* | 0.610 (6) |
C18 | 0.7486 (5) | 0.4907 (5) | 0.3515 (9) | 0.078 (4)* | 0.610 (6) |
C19 | 0.7293 (8) | 0.5341 (7) | 0.3433 (12) | 0.129 (8)* | 0.610 (6) |
H19 | 0.6946 | 0.5393 | 0.3398 | 0.155* | 0.610 (6) |
C20 | 0.7607 (7) | 0.5699 (7) | 0.3403 (12) | 0.114 (9)* | 0.610 (6) |
H20 | 0.7455 | 0.5994 | 0.3319 | 0.137* | 0.610 (6) |
N3 | 0.43078 (19) | 0.16878 (16) | 0.6424 (3) | 0.0371 (11) | |
C21 | 0.4780 (2) | 0.1614 (2) | 0.6374 (4) | 0.0398 (14) | |
H21 | 0.4900 | 0.1309 | 0.6409 | 0.048* | |
C22 | 0.5101 (2) | 0.1961 (2) | 0.6272 (4) | 0.0444 (15) | |
H22 | 0.5431 | 0.1889 | 0.6229 | 0.053* | |
C23 | 0.4949 (3) | 0.2409 (2) | 0.6234 (4) | 0.0527 (18) | |
C24 | 0.4455 (3) | 0.2483 (2) | 0.6277 (5) | 0.0566 (19) | |
H24 | 0.4325 | 0.2785 | 0.6246 | 0.068* | |
C25 | 0.4156 (2) | 0.2121 (2) | 0.6363 (4) | 0.0466 (16) | |
H25 | 0.3819 | 0.2183 | 0.6380 | 0.056* | |
C26 | 0.5259 (3) | 0.2795 (3) | 0.6151 (6) | 0.081 (3) | |
H26 | 0.5099 | 0.3079 | 0.5938 | 0.098* | |
C27 | 0.5774 (3) | 0.2761 (3) | 0.6371 (5) | 0.078 (3) | |
H27 | 0.5929 | 0.2472 | 0.6544 | 0.094* | |
C28 | 0.6100 (6) | 0.3155 (6) | 0.6350 (6) | 0.063 (5)* | 0.610 (6) |
C29 | 0.6617 (6) | 0.3078 (5) | 0.6653 (10) | 0.058 (4)* | 0.610 (6) |
H29 | 0.6737 | 0.2783 | 0.6873 | 0.070* | 0.610 (6) |
C30 | 0.6964 (5) | 0.3409 (5) | 0.6650 (10) | 0.065 (4)* | 0.610 (6) |
H30 | 0.7320 | 0.3351 | 0.6852 | 0.079* | 0.610 (6) |
C31 | 0.6770 (4) | 0.3832 (4) | 0.6337 (10) | 0.060 (3)* | 0.610 (6) |
C32 | 0.6266 (5) | 0.3933 (5) | 0.6072 (11) | 0.079 (4)* | 0.610 (6) |
H32 | 0.6147 | 0.4228 | 0.5844 | 0.095* | 0.610 (6) |
C33 | 0.5936 (5) | 0.3599 (5) | 0.6143 (10) | 0.068 (4)* | 0.610 (6) |
H33 | 0.5587 | 0.3671 | 0.6050 | 0.082* | 0.610 (6) |
C34 | 0.7145 (5) | 0.4190 (4) | 0.6294 (9) | 0.071 (4)* | 0.610 (6) |
H34 | 0.7491 | 0.4099 | 0.6413 | 0.085* | 0.610 (6) |
C35 | 0.7035 (6) | 0.4632 (4) | 0.6100 (9) | 0.083 (4)* | 0.610 (6) |
H35 | 0.6689 | 0.4726 | 0.5921 | 0.100* | 0.610 (6) |
N4 | 0.8204 (3) | 0.5619 (3) | 0.6264 (6) | 0.034 (3)* | 0.610 (6) |
C36 | 0.8290 (4) | 0.5182 (4) | 0.6224 (7) | 0.042 (3)* | 0.610 (6) |
H36 | 0.8619 | 0.5081 | 0.6222 | 0.051* | 0.610 (6) |
C37 | 0.7923 (6) | 0.4873 (6) | 0.6185 (10) | 0.054 (6)* | 0.610 (6) |
H37 | 0.8004 | 0.4558 | 0.6176 | 0.064* | 0.610 (6) |
C38 | 0.7453 (5) | 0.4991 (4) | 0.6159 (8) | 0.053 (3)* | 0.610 (6) |
C39 | 0.7367 (4) | 0.5439 (4) | 0.6221 (8) | 0.045 (3)* | 0.610 (6) |
H39 | 0.7036 | 0.5540 | 0.6207 | 0.054* | 0.610 (6) |
C40 | 0.7738 (4) | 0.5749 (4) | 0.6304 (9) | 0.039 (4)* | 0.610 (6) |
H40 | 0.7673 | 0.6061 | 0.6391 | 0.047* | 0.610 (6) |
C41 | 0.4294 (2) | 0.06515 (17) | 0.5374 (4) | 0.0317 (12) | |
C42 | 0.30854 (19) | 0.17142 (19) | 0.4763 (4) | 0.0335 (13) | |
C43 | 0.2559 (2) | 0.2402 (2) | 0.4140 (4) | 0.0372 (14) | |
H43 | 0.2594 | 0.2331 | 0.3540 | 0.045* | |
C44 | 0.27810 (19) | 0.21240 (18) | 0.4886 (3) | 0.0283 (12) | |
C45 | 0.2715 (2) | 0.2216 (2) | 0.5756 (4) | 0.0373 (14) | |
H45 | 0.2856 | 0.2019 | 0.6274 | 0.045* | |
C46 | 0.4977 (2) | 0.00602 (19) | 0.5898 (4) | 0.0339 (13) | |
H46 | 0.4958 | 0.0100 | 0.6519 | 0.041* | |
C47 | 0.46626 (19) | 0.03103 (16) | 0.5179 (4) | 0.0266 (11) | |
C48 | 0.4681 (2) | 0.02454 (19) | 0.4264 (4) | 0.0348 (13) | |
H48 | 0.4459 | 0.0411 | 0.3760 | 0.042* | |
C49 | 0.3636 (2) | 0.1148 (2) | 0.1958 (4) | 0.0486 (16) | |
C50 | 0.3750 (3) | 0.1331 (3) | 0.8143 (5) | 0.063 (2) | |
C51 | 0.3402 (2) | 0.1538 (2) | 0.0395 (4) | 0.0448 (15) | |
H51 | 0.3189 | 0.1735 | 0.0618 | 0.054* | |
C52 | 0.3687 (2) | 0.1203 (2) | 0.0975 (4) | 0.0376 (14) | |
C53 | 0.3995 (2) | 0.0918 (2) | 0.0649 (4) | 0.0377 (14) | |
H53 | 0.4189 | 0.0688 | 0.1045 | 0.045* | |
C54 | 0.4020 (2) | 0.0967 (2) | 0.9744 (4) | 0.0435 (15) | |
H54 | 0.4236 | 0.0772 | 0.9522 | 0.052* | |
C55 | 0.3737 (2) | 0.1296 (2) | 0.9156 (4) | 0.0425 (15) | |
C56 | 0.3433 (2) | 0.1583 (2) | 0.9473 (4) | 0.0496 (17) | |
H56 | 0.3242 | 0.1813 | 0.9072 | 0.060* | |
C8A | 0.615 (3) | 0.311 (3) | 0.365 (2) | 0.34 (5)* | 0.390 (6) |
C9A | 0.6585 (8) | 0.2936 (7) | 0.3977 (14) | 0.072 (6)* | 0.390 (6) |
H9A | 0.6653 | 0.2622 | 0.4118 | 0.086* | 0.390 (6) |
C10A | 0.6939 (8) | 0.3272 (6) | 0.4100 (13) | 0.063 (5)* | 0.390 (6) |
H10A | 0.7295 | 0.3216 | 0.4250 | 0.076* | 0.390 (6) |
C11A | 0.6732 (8) | 0.3701 (6) | 0.3985 (14) | 0.058 (5)* | 0.390 (6) |
C12A | 0.6241 (15) | 0.3820 (13) | 0.349 (4) | 0.38 (6)* | 0.390 (6) |
H12A | 0.6141 | 0.4125 | 0.3307 | 0.461* | 0.390 (6) |
C13A | 0.5912 (9) | 0.3460 (8) | 0.3272 (18) | 0.078 (7)* | 0.390 (6) |
H13A | 0.5564 | 0.3471 | 0.2908 | 0.094* | 0.390 (6) |
C14A | 0.7164 (8) | 0.4069 (6) | 0.4474 (12) | 0.072 (6)* | 0.390 (6) |
H14A | 0.7502 | 0.3993 | 0.4388 | 0.086* | 0.390 (6) |
C15A | 0.7026 (8) | 0.4589 (6) | 0.4303 (12) | 0.074 (6)* | 0.390 (6) |
H15A | 0.6666 | 0.4629 | 0.3902 | 0.089* | 0.390 (6) |
N2A | 0.8022 (5) | 0.5558 (5) | 0.3554 (8) | 0.034 (4)* | 0.390 (6) |
C16A | 0.8155 (7) | 0.5150 (6) | 0.3701 (10) | 0.045 (5)* | 0.390 (6) |
H16A | 0.8482 | 0.5065 | 0.3662 | 0.054* | 0.390 (6) |
C17A | 0.7847 (6) | 0.4812 (5) | 0.3921 (10) | 0.045 (4)* | 0.390 (6) |
H17A | 0.7976 | 0.4510 | 0.4031 | 0.054* | 0.390 (6) |
C18A | 0.7379 (6) | 0.4895 (6) | 0.3983 (11) | 0.057 (5)* | 0.390 (6) |
C19A | 0.7286 (7) | 0.5333 (6) | 0.3840 (12) | 0.051 (5)* | 0.390 (6) |
H19A | 0.6960 | 0.5433 | 0.3862 | 0.061* | 0.390 (6) |
C20A | 0.7607 (7) | 0.5673 (7) | 0.3659 (14) | 0.049 (5)* | 0.390 (6) |
H20A | 0.7508 | 0.5985 | 0.3619 | 0.059* | 0.390 (6) |
C28A | 0.6152 (9) | 0.3119 (8) | 0.6185 (8) | 0.057 (7)* | 0.390 (6) |
C29A | 0.6676 (8) | 0.3036 (7) | 0.6431 (14) | 0.050 (6)* | 0.390 (6) |
H29A | 0.6814 | 0.2751 | 0.6683 | 0.060* | 0.390 (6) |
C30A | 0.6991 (8) | 0.3387 (7) | 0.6293 (16) | 0.067 (7)* | 0.390 (6) |
H30A | 0.7348 | 0.3331 | 0.6488 | 0.080* | 0.390 (6) |
C31A | 0.6831 (6) | 0.3814 (6) | 0.5896 (14) | 0.056 (5)* | 0.390 (6) |
C32A | 0.6298 (7) | 0.3861 (7) | 0.5625 (15) | 0.066 (6)* | 0.390 (6) |
H32A | 0.6159 | 0.4139 | 0.5334 | 0.079* | 0.390 (6) |
C33A | 0.5960 (6) | 0.3532 (5) | 0.5750 (12) | 0.041 (4)* | 0.390 (6) |
H33A | 0.5603 | 0.3586 | 0.5543 | 0.049* | 0.390 (6) |
C34A | 0.7188 (8) | 0.4110 (6) | 0.5558 (13) | 0.066 (5)* | 0.390 (6) |
H34A | 0.7546 | 0.4066 | 0.5964 | 0.080* | 0.390 (6) |
C35A | 0.7064 (9) | 0.4628 (6) | 0.5412 (12) | 0.078 (6)* | 0.390 (6) |
H35A | 0.6738 | 0.4720 | 0.5533 | 0.093* | 0.390 (6) |
N4A | 0.8257 (6) | 0.5652 (5) | 0.6546 (10) | 0.038 (4)* | 0.390 (6) |
C36A | 0.7752 (11) | 0.5722 (10) | 0.6161 (15) | 0.112 (17)* | 0.390 (6) |
H36A | 0.7642 | 0.6030 | 0.6119 | 0.134* | 0.390 (6) |
C37A | 0.7352 (8) | 0.5378 (6) | 0.5800 (13) | 0.062 (6)* | 0.390 (6) |
H37A | 0.7006 | 0.5466 | 0.5538 | 0.074* | 0.390 (6) |
C38A | 0.7492 (6) | 0.4921 (5) | 0.5850 (10) | 0.032 (4)* | 0.390 (6) |
C39A | 0.8008 (9) | 0.4828 (9) | 0.6188 (15) | 0.057 (11)* | 0.390 (6) |
H39A | 0.8133 | 0.4526 | 0.6184 | 0.068* | 0.390 (6) |
C40A | 0.8357 (6) | 0.5207 (5) | 0.6551 (11) | 0.028 (4)* | 0.390 (6) |
H40A | 0.8703 | 0.5125 | 0.6830 | 0.034* | 0.390 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0631 (5) | 0.0617 (5) | 0.0292 (4) | 0.0353 (4) | 0.0215 (3) | 0.0027 (3) |
Zn2 | 0.0431 (4) | 0.0339 (4) | 0.0357 (4) | 0.0114 (3) | 0.0227 (3) | 0.0030 (3) |
O1 | 0.052 (3) | 0.063 (3) | 0.051 (3) | 0.036 (2) | 0.009 (2) | −0.003 (2) |
O2 | 0.053 (3) | 0.037 (2) | 0.049 (3) | 0.0067 (19) | 0.038 (2) | −0.0021 (19) |
O3 | 0.063 (3) | 0.065 (3) | 0.038 (2) | 0.037 (2) | 0.028 (2) | 0.003 (2) |
O4 | 0.047 (3) | 0.045 (3) | 0.048 (3) | 0.012 (2) | 0.020 (2) | 0.008 (2) |
O5 | 0.071 (3) | 0.097 (4) | 0.037 (3) | 0.024 (3) | 0.033 (2) | −0.003 (3) |
O6 | 0.072 (3) | 0.069 (3) | 0.030 (2) | 0.014 (3) | 0.016 (2) | 0.011 (2) |
O7 | 0.083 (4) | 0.166 (6) | 0.040 (3) | −0.012 (4) | 0.020 (3) | 0.041 (4) |
O8 | 0.113 (5) | 0.088 (4) | 0.051 (3) | −0.038 (3) | 0.063 (3) | −0.015 (3) |
N1 | 0.064 (4) | 0.058 (4) | 0.049 (3) | 0.017 (3) | 0.029 (3) | −0.005 (3) |
C1 | 0.065 (5) | 0.056 (4) | 0.055 (4) | 0.009 (4) | 0.020 (4) | −0.001 (3) |
C2 | 0.071 (6) | 0.073 (6) | 0.058 (5) | −0.006 (4) | 0.010 (4) | 0.007 (4) |
C3 | 0.089 (7) | 0.067 (6) | 0.067 (6) | 0.003 (5) | 0.014 (5) | 0.006 (4) |
C4 | 0.137 (10) | 0.051 (5) | 0.134 (9) | 0.012 (6) | 0.080 (8) | 0.014 (5) |
C5 | 0.096 (7) | 0.066 (6) | 0.089 (6) | 0.023 (5) | 0.048 (5) | 0.015 (5) |
C6 | 0.081 (7) | 0.122 (9) | 0.145 (11) | −0.022 (7) | 0.044 (7) | −0.012 (8) |
C7 | 0.118 (9) | 0.090 (7) | 0.100 (8) | −0.016 (7) | 0.014 (7) | 0.002 (6) |
N3 | 0.050 (3) | 0.036 (3) | 0.025 (2) | 0.007 (2) | 0.010 (2) | 0.001 (2) |
C21 | 0.047 (4) | 0.044 (4) | 0.026 (3) | 0.002 (3) | 0.007 (3) | −0.004 (3) |
C22 | 0.038 (3) | 0.052 (4) | 0.040 (4) | 0.003 (3) | 0.008 (3) | −0.001 (3) |
C23 | 0.053 (5) | 0.051 (4) | 0.044 (4) | −0.008 (3) | −0.001 (3) | −0.001 (3) |
C24 | 0.048 (4) | 0.034 (4) | 0.075 (5) | 0.006 (3) | −0.002 (4) | −0.003 (3) |
C25 | 0.046 (4) | 0.043 (4) | 0.048 (4) | 0.009 (3) | 0.008 (3) | 0.001 (3) |
C26 | 0.056 (5) | 0.078 (6) | 0.100 (7) | −0.016 (4) | 0.006 (5) | 0.021 (5) |
C27 | 0.082 (6) | 0.069 (5) | 0.070 (5) | −0.019 (5) | 0.000 (5) | 0.014 (4) |
C41 | 0.025 (3) | 0.025 (3) | 0.049 (4) | −0.003 (2) | 0.018 (3) | −0.004 (3) |
C42 | 0.022 (3) | 0.038 (3) | 0.039 (3) | 0.007 (2) | 0.007 (2) | 0.002 (3) |
C43 | 0.032 (3) | 0.054 (4) | 0.030 (3) | 0.011 (3) | 0.014 (2) | −0.001 (3) |
C44 | 0.026 (3) | 0.042 (3) | 0.021 (3) | 0.005 (2) | 0.014 (2) | −0.001 (2) |
C45 | 0.041 (3) | 0.044 (3) | 0.029 (3) | 0.010 (3) | 0.015 (3) | 0.007 (3) |
C46 | 0.044 (3) | 0.038 (3) | 0.028 (3) | 0.001 (3) | 0.022 (3) | 0.000 (2) |
C47 | 0.028 (3) | 0.023 (3) | 0.034 (3) | −0.002 (2) | 0.016 (2) | −0.008 (2) |
C48 | 0.040 (3) | 0.038 (3) | 0.029 (3) | 0.005 (3) | 0.013 (2) | 0.001 (2) |
C49 | 0.048 (4) | 0.066 (4) | 0.036 (3) | 0.012 (3) | 0.020 (3) | −0.008 (3) |
C50 | 0.062 (5) | 0.097 (6) | 0.035 (4) | −0.036 (5) | 0.021 (4) | 0.001 (4) |
C51 | 0.046 (4) | 0.055 (4) | 0.041 (3) | 0.010 (3) | 0.024 (3) | −0.004 (3) |
C52 | 0.028 (3) | 0.054 (4) | 0.032 (3) | 0.005 (3) | 0.011 (2) | −0.001 (3) |
C53 | 0.043 (3) | 0.038 (3) | 0.033 (3) | 0.006 (3) | 0.012 (3) | 0.003 (3) |
C54 | 0.052 (4) | 0.045 (4) | 0.043 (4) | −0.010 (3) | 0.028 (3) | −0.004 (3) |
C55 | 0.036 (3) | 0.060 (4) | 0.034 (3) | −0.003 (3) | 0.013 (3) | −0.003 (3) |
C56 | 0.055 (4) | 0.050 (4) | 0.043 (4) | 0.014 (3) | 0.012 (3) | 0.025 (3) |
Zn1—N2i | 1.970 (12) | C32—C33 | 1.360 (16) |
Zn1—O3 | 2.004 (4) | C34—C35 | 1.342 (13) |
Zn1—O1 | 2.005 (4) | C35—C38 | 1.539 (19) |
Zn1—O5 | 2.128 (4) | N4—C36 | 1.308 (12) |
Zn1—N1 | 2.183 (6) | N4—C40 | 1.351 (13) |
Zn1—O6 | 2.301 (4) | N4—Zn2ii | 2.202 (10) |
Zn1—N2Ai | 2.424 (16) | C36—C37 | 1.342 (17) |
Zn1—C49 | 2.497 (6) | C37—C38 | 1.325 (16) |
Zn2—O2 | 2.011 (4) | C38—C39 | 1.341 (14) |
Zn2—O8 | 2.034 (5) | C39—C40 | 1.342 (14) |
Zn2—O4 | 2.045 (4) | C41—C47 | 1.509 (7) |
Zn2—N4Ai | 2.102 (16) | C42—C44 | 1.504 (7) |
Zn2—N3 | 2.129 (5) | C43—C44 | 1.368 (7) |
Zn2—N4i | 2.202 (10) | C43—C45iii | 1.383 (8) |
O1—C41 | 1.221 (7) | C44—C45 | 1.389 (7) |
O2—C41 | 1.233 (6) | C45—C43iii | 1.383 (8) |
O3—C42 | 1.246 (7) | C46—C48iv | 1.368 (7) |
O4—C42 | 1.234 (6) | C46—C47 | 1.374 (7) |
O5—C49 | 1.258 (7) | C47—C48 | 1.393 (7) |
O6—C49 | 1.235 (7) | C48—C46iv | 1.368 (7) |
O7—C50 | 1.254 (10) | C49—C52 | 1.521 (8) |
O8—C50 | 1.237 (10) | C50—C55 | 1.525 (9) |
N1—C5 | 1.335 (9) | C51—C52 | 1.387 (8) |
N1—C1 | 1.346 (9) | C51—C56v | 1.408 (8) |
C1—C2 | 1.332 (10) | C52—C53 | 1.374 (8) |
C2—C3 | 1.374 (11) | C53—C54v | 1.379 (8) |
C3—C4 | 1.353 (12) | C54—C55 | 1.378 (9) |
C3—C6 | 1.461 (13) | C54—C53vi | 1.379 (8) |
C4—C5 | 1.384 (12) | C55—C56 | 1.363 (9) |
C6—C7 | 1.354 (11) | C56—C51vi | 1.408 (8) |
C7—C8 | 1.490 (18) | C8A—C9A | 1.25 (4) |
C7—C8A | 1.70 (11) | C8A—C13A | 1.26 (4) |
C8—C9 | 1.41 (2) | C9A—C10A | 1.36 (3) |
C8—C13 | 1.43 (2) | C10A—C11A | 1.37 (2) |
C9—C10 | 1.46 (2) | C11A—C12A | 1.38 (3) |
C10—C11 | 1.432 (19) | C11A—C14A | 1.61 (3) |
C11—C12 | 1.421 (18) | C12A—C13A | 1.37 (3) |
C11—C14 | 1.43 (2) | C14A—C15A | 1.574 (18) |
C12—C13 | 1.48 (2) | C14A—C34A | 1.601 (18) |
C14—C15 | 1.340 (14) | C15A—C18A | 1.50 (3) |
C15—C18 | 1.51 (2) | C15A—C35A | 1.629 (18) |
N2—C20 | 1.376 (18) | N2A—C20A | 1.240 (19) |
N2—C16 | 1.388 (15) | N2A—C16A | 1.249 (18) |
N2—Zn1ii | 1.970 (12) | N2A—Zn1ii | 2.424 (16) |
C16—C17 | 1.372 (17) | C16A—C17A | 1.40 (2) |
C17—C18 | 1.356 (16) | C17A—C18A | 1.334 (19) |
C18—C19 | 1.368 (17) | C18A—C19A | 1.314 (19) |
C19—C20 | 1.37 (2) | C19A—C20A | 1.41 (2) |
N3—C25 | 1.332 (7) | C28A—C29A | 1.40 (2) |
N3—C21 | 1.336 (7) | C28A—C33A | 1.40 (2) |
C21—C22 | 1.383 (8) | C29A—C30A | 1.40 (2) |
C22—C23 | 1.373 (9) | C30A—C31A | 1.40 (2) |
C23—C24 | 1.394 (9) | C31A—C32A | 1.40 (2) |
C23—C26 | 1.442 (10) | C31A—C34A | 1.50 (3) |
C24—C25 | 1.370 (9) | C32A—C33A | 1.39 (2) |
C26—C27 | 1.357 (10) | C34A—C35A | 1.557 (18) |
C27—C28 | 1.47 (2) | C35A—C38A | 1.45 (3) |
C27—C28A | 1.56 (3) | N4A—C40A | 1.332 (19) |
C28—C29 | 1.376 (16) | N4A—C36A | 1.35 (2) |
C28—C33 | 1.380 (16) | N4A—Zn2ii | 2.102 (16) |
C29—C30 | 1.358 (16) | C36A—C37A | 1.47 (3) |
C30—C31 | 1.376 (14) | C37A—C38A | 1.39 (2) |
C31—C32 | 1.356 (14) | C38A—C39A | 1.38 (2) |
C31—C34 | 1.483 (18) | C39A—C40A | 1.46 (3) |
N2i—Zn1—O3 | 96.5 (3) | C30—C31—C34 | 116.6 (11) |
N2i—Zn1—O1 | 89.4 (3) | C31—C32—C33 | 117.8 (13) |
O3—Zn1—O1 | 110.35 (17) | C32—C33—C28 | 121.0 (14) |
N2i—Zn1—O5 | 94.8 (3) | C35—C34—C31 | 125.2 (13) |
O3—Zn1—O5 | 91.52 (17) | C34—C35—C38 | 122.1 (13) |
O1—Zn1—O5 | 157.15 (17) | C36—N4—C40 | 117.5 (10) |
N2i—Zn1—N1 | 171.9 (3) | C36—N4—Zn2ii | 123.1 (7) |
O3—Zn1—N1 | 91.3 (2) | C40—N4—Zn2ii | 118.7 (7) |
O1—Zn1—N1 | 85.8 (2) | N4—C36—C37 | 121.3 (12) |
O5—Zn1—N1 | 87.2 (2) | C38—C37—C36 | 122.5 (15) |
N2i—Zn1—O6 | 90.1 (3) | C37—C38—C39 | 116.2 (14) |
O3—Zn1—O6 | 150.87 (17) | C37—C38—C35 | 121.7 (12) |
O1—Zn1—O6 | 98.03 (16) | C39—C38—C35 | 122.0 (11) |
O5—Zn1—O6 | 59.59 (16) | C38—C39—C40 | 121.6 (11) |
N1—Zn1—O6 | 84.13 (18) | C39—C40—N4 | 120.6 (11) |
O3—Zn1—N2Ai | 95.4 (3) | O1—C41—O2 | 124.6 (5) |
O1—Zn1—N2Ai | 86.7 (3) | O1—C41—C47 | 119.1 (5) |
O5—Zn1—N2Ai | 98.1 (3) | O2—C41—C47 | 116.2 (5) |
N1—Zn1—N2Ai | 171.3 (3) | O4—C42—O3 | 125.4 (5) |
O6—Zn1—N2Ai | 92.5 (3) | O4—C42—C44 | 118.0 (5) |
N2i—Zn1—C49 | 94.9 (3) | O3—C42—C44 | 116.6 (5) |
O3—Zn1—C49 | 121.42 (19) | C44—C43—C45iii | 121.2 (5) |
O1—Zn1—C49 | 127.06 (19) | C43—C44—C45 | 119.7 (5) |
O5—Zn1—C49 | 30.24 (18) | C43—C44—C42 | 120.5 (5) |
N1—Zn1—C49 | 82.8 (2) | C45—C44—C42 | 119.9 (5) |
O6—Zn1—C49 | 29.49 (17) | C43iii—C45—C44 | 119.1 (5) |
N2Ai—Zn1—C49 | 98.2 (3) | C48iv—C46—C47 | 121.2 (5) |
O2—Zn2—O8 | 97.2 (2) | C46—C47—C48 | 119.7 (5) |
O2—Zn2—O4 | 122.43 (17) | C46—C47—C41 | 120.4 (5) |
O8—Zn2—O4 | 139.7 (2) | C48—C47—C41 | 119.9 (5) |
O2—Zn2—N4Ai | 93.0 (4) | C46iv—C48—C47 | 119.1 (5) |
O8—Zn2—N4Ai | 82.9 (4) | O6—C49—O5 | 124.4 (6) |
O4—Zn2—N4Ai | 87.8 (4) | O6—C49—C52 | 118.7 (5) |
O2—Zn2—N3 | 93.31 (17) | O5—C49—C52 | 116.9 (6) |
O8—Zn2—N3 | 96.54 (18) | O6—C49—Zn1 | 66.4 (3) |
O4—Zn2—N3 | 88.66 (17) | O5—C49—Zn1 | 58.4 (3) |
O2—Zn2—N4i | 89.5 (2) | C52—C49—Zn1 | 170.2 (5) |
O8—Zn2—N4i | 93.3 (3) | O8—C50—O7 | 125.2 (7) |
O4—Zn2—N4i | 81.2 (2) | O8—C50—C55 | 117.3 (7) |
N3—Zn2—N4i | 169.3 (2) | O7—C50—C55 | 117.5 (8) |
C41—O1—Zn1 | 167.3 (4) | C52—C51—C56v | 119.4 (5) |
C41—O2—Zn2 | 116.7 (4) | C53—C52—C51 | 120.1 (5) |
C42—O3—Zn1 | 127.2 (4) | C53—C52—C49 | 121.1 (5) |
C42—O4—Zn2 | 155.1 (4) | C51—C52—C49 | 118.8 (5) |
C49—O5—Zn1 | 91.3 (4) | C52—C53—C54v | 119.6 (6) |
C49—O6—Zn1 | 84.1 (4) | C55—C54—C53vi | 121.0 (6) |
C50—O8—Zn2 | 102.8 (5) | C56—C55—C54 | 120.0 (6) |
C5—N1—C1 | 113.8 (7) | C56—C55—C50 | 119.8 (6) |
C5—N1—Zn1 | 122.4 (6) | C54—C55—C50 | 120.2 (6) |
C1—N1—Zn1 | 123.7 (5) | C55—C56—C51vi | 119.9 (6) |
C2—C1—N1 | 126.2 (7) | C9A—C8A—C13A | 145 (10) |
C1—C2—C3 | 120.2 (8) | C9A—C8A—C7 | 99 (5) |
C4—C3—C2 | 114.9 (9) | C13A—C8A—C7 | 115 (6) |
C4—C3—C6 | 119.6 (9) | C8A—C9A—C10A | 108 (5) |
C2—C3—C6 | 125.5 (9) | C9A—C10A—C11A | 113.1 (19) |
C3—C4—C5 | 122.2 (9) | C10A—C11A—C12A | 127 (3) |
N1—C5—C4 | 122.3 (8) | C10A—C11A—C14A | 109.5 (16) |
C7—C6—C3 | 126.6 (11) | C12A—C11A—C14A | 123 (2) |
C6—C7—C8 | 124.5 (11) | C13A—C12A—C11A | 114 (3) |
C6—C7—C8A | 116.0 (13) | C8A—C13A—C12A | 107 (5) |
C9—C8—C13 | 125.0 (17) | C15A—C14A—C34A | 91.6 (12) |
C9—C8—C7 | 119.3 (12) | C15A—C14A—C11A | 117.8 (16) |
C13—C8—C7 | 115.6 (13) | C34A—C14A—C11A | 108.3 (15) |
C8—C9—C10 | 117.3 (16) | C18A—C15A—C14A | 118.9 (16) |
C11—C10—C9 | 122.1 (18) | C18A—C15A—C35A | 115.3 (14) |
C12—C11—C10 | 114.3 (17) | C14A—C15A—C35A | 87.8 (12) |
C12—C11—C14 | 125.7 (15) | C20A—N2A—C16A | 118.0 (19) |
C10—C11—C14 | 116.7 (16) | C20A—N2A—Zn1ii | 112.9 (11) |
C11—C12—C13 | 125.1 (17) | C16A—N2A—Zn1ii | 125.7 (12) |
C8—C13—C12 | 112.6 (18) | N2A—C16A—C17A | 123.5 (17) |
C15—C14—C11 | 122.2 (17) | C18A—C17A—C16A | 122.9 (16) |
C14—C15—C18 | 126.1 (17) | C19A—C18A—C17A | 108.4 (18) |
C20—N2—C16 | 110.6 (15) | C19A—C18A—C15A | 121.4 (16) |
C20—N2—Zn1ii | 126.7 (11) | C17A—C18A—C15A | 129.6 (15) |
C16—N2—Zn1ii | 122.4 (9) | C18A—C19A—C20A | 128.2 (18) |
C17—C16—N2 | 124.9 (13) | N2A—C20A—C19A | 118.7 (17) |
C18—C17—C16 | 120.6 (13) | C29A—C28A—C33A | 119 (2) |
C17—C18—C19 | 117.6 (16) | C28A—C29A—C30A | 117.8 (19) |
C17—C18—C15 | 125.4 (14) | C31A—C30A—C29A | 126.1 (19) |
C19—C18—C15 | 116.9 (14) | C30A—C31A—C32A | 112.4 (19) |
C20—C19—C18 | 119.1 (19) | C30A—C31A—C34A | 120.3 (16) |
C19—C20—N2 | 126.8 (19) | C32A—C31A—C34A | 124.9 (16) |
C25—N3—C21 | 116.1 (5) | C33A—C32A—C31A | 124.9 (17) |
C25—N3—Zn2 | 122.0 (4) | C32A—C33A—C28A | 119.2 (18) |
C21—N3—Zn2 | 121.7 (4) | C31A—C34A—C35A | 118.2 (16) |
N3—C21—C22 | 123.1 (6) | C31A—C34A—C14A | 117.2 (16) |
C23—C22—C21 | 120.9 (6) | C35A—C34A—C14A | 89.4 (12) |
C22—C23—C24 | 115.8 (6) | C38A—C35A—C34A | 113.7 (16) |
C22—C23—C26 | 125.1 (7) | C38A—C35A—C15A | 107.6 (14) |
C24—C23—C26 | 119.1 (7) | C34A—C35A—C15A | 91.2 (12) |
C25—C24—C23 | 120.1 (6) | C40A—N4A—C36A | 109 (2) |
N3—C25—C24 | 124.1 (6) | C40A—N4A—Zn2ii | 121.1 (11) |
C27—C26—C23 | 121.3 (8) | C36A—N4A—Zn2ii | 122.5 (13) |
C26—C27—C28 | 122.4 (9) | N4A—C36A—C37A | 128 (2) |
C29—C28—C33 | 117.7 (17) | C38A—C37A—C36A | 118 (2) |
C29—C28—C27 | 116.2 (12) | C39A—C38A—C37A | 117 (2) |
C33—C28—C27 | 125.8 (13) | C39A—C38A—C35A | 130.9 (16) |
C30—C29—C28 | 122.5 (14) | C37A—C38A—C35A | 111.9 (15) |
C29—C30—C31 | 116.3 (13) | C38A—C39A—C40A | 118 (2) |
C32—C31—C30 | 123.7 (14) | N4A—C40A—C39A | 129.1 (17) |
C32—C31—C34 | 119.7 (11) |
Symmetry codes: (i) x−1/2, y−1/2, z; (ii) x+1/2, y+1/2, z; (iii) −x+1/2, −y+1/2, −z+1; (iv) −x+1, −y, −z+1; (v) x, y, z−1; (vi) x, y, z+1. |
C56H40N4O8Zn2 | Dx = 1.125 Mg m−3 |
Mr = 1027.66 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pcca | Cell parameters from 9984 reflections |
a = 20.030 (3) Å | θ = 2.3–27.3° |
b = 20.005 (3) Å | µ = 0.84 mm−1 |
c = 15.145 (2) Å | T = 173 K |
V = 6068.8 (14) Å3 | Block, red |
Z = 4 | 0.46 × 0.41 × 0.30 mm |
F(000) = 2112 |
Bruker APEX-II CCD diffractometer | 3975 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.074 |
Absorption correction: multi-scan SADABS (Sheldrick, 2011) | θmax = 26.0°, θmin = 2.0° |
Tmin = 0.703, Tmax = 0.801 | h = −24→24 |
46693 measured reflections | k = −24→24 |
5979 independent reflections | l = −18→18 |
Refinement on F2 | 440 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.073 | H-atom parameters constrained |
wR(F2) = 0.231 | w = 1/[σ2(Fo2) + (0.1154P)2 + 7.2582P] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max = 0.001 |
5979 reflections | Δρmax = 0.91 e Å−3 |
294 parameters | Δρmin = −0.72 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Crystallized in the orthorhombic space group Pcca with Z = 4. The asymmetric unit contains half of the formula unit. The dimer formed by dimerization of trans,cis,trans-bpeb disordered due to crystallographic centre of inversion. Due to this disorder soft constraints (FLAT, SAME, SADI) were used to retain the geometry of molecule. Only isotropic thermal parameter could be refined for these bpeb-dimer fragment. Again one DMF was disordered by crystallographic inversion centre. The rest of the electron densities were too complicated to resolve. Hence they were assigned as O atoms of water molecules. They could as well be highly disordered DMF.[Zn2(bdc)2(dimer)].DMF.6.5H2O. For uniformity, the referee suggested to squeeze the data and hence squeezed. The agreement factors of the squeezed better than the unsqueezed data. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Zn1 | 0.43270 (3) | 0.66969 (2) | 0.85781 (3) | 0.0250 (2) | |
O1 | 0.52593 (15) | 0.67007 (14) | 0.9065 (2) | 0.0355 (8) | |
O2 | 0.57615 (18) | 0.67078 (17) | 0.7764 (2) | 0.0449 (9) | |
O3 | 0.8303 (2) | 0.67234 (15) | 1.1227 (3) | 0.0521 (11) | |
O4 | 0.8841 (2) | 0.67063 (16) | 0.9961 (3) | 0.0565 (11) | |
N1 | 0.4379 (6) | 0.5644 (5) | 0.8558 (8) | 0.024 (4)* | 0.5 |
C1 | 0.4867 (6) | 0.5310 (5) | 0.8977 (8) | 0.034 (4)* | 0.5 |
H1 | 0.5149 | 0.5556 | 0.9363 | 0.041* | 0.5 |
C2 | 0.4988 (5) | 0.4633 (4) | 0.8886 (7) | 0.029 (3)* | 0.5 |
H2A | 0.5336 | 0.4426 | 0.9212 | 0.035* | 0.5 |
C3 | 0.4601 (5) | 0.4260 (4) | 0.8318 (7) | 0.024 (2)* | 0.5 |
C4 | 0.4064 (6) | 0.4579 (4) | 0.7932 (7) | 0.030 (3)* | 0.5 |
H4 | 0.3767 | 0.4339 | 0.7560 | 0.037* | 0.5 |
C5 | 0.3963 (6) | 0.5258 (5) | 0.8095 (9) | 0.033 (4)* | 0.5 |
H5 | 0.3571 | 0.5459 | 0.7861 | 0.039* | 0.5 |
C6 | 0.4863 (5) | 0.3575 (4) | 0.8109 (6) | 0.033 (2)* | 0.5 |
H6 | 0.5062 | 0.3358 | 0.8642 | 0.040* | 0.5 |
C7 | 0.4391 (5) | 0.3084 (5) | 0.7602 (6) | 0.043 (2)* | 0.5 |
H7 | 0.3970 | 0.3321 | 0.7435 | 0.052* | 0.5 |
C8 | 0.4224 (5) | 0.2409 (5) | 0.8006 (7) | 0.051 (3)* | 0.5 |
C9 | 0.4677 (6) | 0.2060 (4) | 0.8435 (6) | 0.041 (2)* | 0.5 |
H9 | 0.5039 | 0.2299 | 0.8690 | 0.049* | 0.5 |
C10 | 0.4669 (6) | 0.1379 (5) | 0.8546 (7) | 0.059 (3)* | 0.5 |
H10 | 0.4991 | 0.1165 | 0.8909 | 0.071* | 0.5 |
C11 | 0.4195 (7) | 0.1021 (6) | 0.8128 (10) | 0.079 (4)* | 0.5 |
C12 | 0.3664 (7) | 0.1385 (5) | 0.7824 (9) | 0.073 (4)* | 0.5 |
H12 | 0.3265 | 0.1159 | 0.7664 | 0.087* | 0.5 |
C13 | 0.3694 (7) | 0.2077 (5) | 0.7745 (9) | 0.079 (4)* | 0.5 |
H13 | 0.3327 | 0.2312 | 0.7498 | 0.095* | 0.5 |
C14 | 0.4371 (8) | 0.0329 (8) | 0.7736 (10) | 0.108 (6)* | 0.5 |
H14 | 0.3942 | 0.0089 | 0.7618 | 0.129* | 0.5 |
C15 | 0.4872 (8) | −0.0191 (7) | 0.8174 (10) | 0.103 (6)* | 0.5 |
H15 | 0.5116 | 0.0024 | 0.8676 | 0.123* | 0.5 |
N2 | 0.4371 (5) | −0.2216 (4) | 0.8662 (7) | 0.027 (3)* | 0.5 |
C16 | 0.3959 (6) | −0.1848 (5) | 0.8195 (8) | 0.045 (3)* | 0.5 |
H16 | 0.3607 | −0.2070 | 0.7893 | 0.054* | 0.5 |
C17 | 0.4001 (7) | −0.1157 (6) | 0.8108 (11) | 0.084 (5)* | 0.5 |
H17 | 0.3668 | −0.0909 | 0.7804 | 0.101* | 0.5 |
C18 | 0.4543 (6) | −0.0853 (5) | 0.8480 (9) | 0.058 (4)* | 0.5 |
C19 | 0.4928 (6) | −0.1198 (5) | 0.9043 (9) | 0.058 (4)* | 0.5 |
H19 | 0.5261 | −0.0978 | 0.9383 | 0.070* | 0.5 |
C20 | 0.4830 (6) | −0.1884 (5) | 0.9119 (9) | 0.041 (3)* | 0.5 |
H20 | 0.5105 | −0.2127 | 0.9516 | 0.050* | 0.5 |
N3 | 0.5710 (6) | 0.5599 (6) | 0.6504 (8) | 0.031 (5)* | 0.5 |
C21 | 0.5219 (6) | 0.5235 (5) | 0.6137 (8) | 0.038 (5)* | 0.5 |
H21 | 0.4923 | 0.5442 | 0.5731 | 0.046* | 0.5 |
C22 | 0.5134 (6) | 0.4561 (5) | 0.6339 (8) | 0.040 (3)* | 0.5 |
H22 | 0.4785 | 0.4316 | 0.6063 | 0.048* | 0.5 |
C23 | 0.5551 (5) | 0.4247 (4) | 0.6936 (7) | 0.033 (3)* | 0.5 |
C24 | 0.6073 (6) | 0.4620 (5) | 0.7256 (8) | 0.036 (3)* | 0.5 |
H24 | 0.6403 | 0.4414 | 0.7615 | 0.043* | 0.5 |
C25 | 0.6122 (6) | 0.5296 (5) | 0.7058 (8) | 0.026 (3)* | 0.5 |
H25 | 0.6465 | 0.5551 | 0.7331 | 0.031* | 0.5 |
C26 | 0.5369 (5) | 0.3566 (4) | 0.7298 (6) | 0.038 (2)* | 0.5 |
H26 | 0.5784 | 0.3321 | 0.7471 | 0.045* | 0.5 |
C27 | 0.4897 (5) | 0.3085 (5) | 0.6782 (6) | 0.049 (3)* | 0.5 |
H27 | 0.4694 | 0.3320 | 0.6265 | 0.059* | 0.5 |
C28 | 0.5137 (7) | 0.2388 (6) | 0.6514 (9) | 0.073 (4)* | 0.5 |
C29 | 0.5648 (8) | 0.2054 (7) | 0.6847 (12) | 0.099 (6)* | 0.5 |
H29 | 0.6006 | 0.2289 | 0.7118 | 0.119* | 0.5 |
C30 | 0.5661 (9) | 0.1352 (8) | 0.6801 (15) | 0.126 (8)* | 0.5 |
H30 | 0.6059 | 0.1125 | 0.6963 | 0.151* | 0.5 |
C31 | 0.5126 (9) | 0.0986 (7) | 0.6532 (12) | 0.106 (6)* | 0.5 |
C32 | 0.4692 (10) | 0.1341 (8) | 0.6038 (14) | 0.139 (7)* | 0.5 |
H32 | 0.4394 | 0.1115 | 0.5653 | 0.166* | 0.5 |
C33 | 0.4680 (8) | 0.2029 (7) | 0.6086 (11) | 0.102 (5)* | 0.5 |
H33 | 0.4326 | 0.2260 | 0.5799 | 0.122* | 0.5 |
C34 | 0.4806 (8) | 0.0313 (7) | 0.6838 (9) | 0.094 (5)* | 0.5 |
H34 | 0.4560 | 0.0088 | 0.6347 | 0.113* | 0.5 |
C35 | 0.5328 (8) | −0.0178 (7) | 0.7296 (10) | 0.107 (6)* | 0.5 |
H35 | 0.5749 | 0.0074 | 0.7423 | 0.129* | 0.5 |
N4 | 0.5664 (5) | −0.2225 (5) | 0.6544 (7) | 0.036 (3)* | 0.5 |
C36 | 0.6065 (5) | −0.1894 (5) | 0.7073 (8) | 0.039 (3)* | 0.5 |
H36 | 0.6414 | −0.2130 | 0.7361 | 0.047* | 0.5 |
C37 | 0.5999 (6) | −0.1224 (5) | 0.7227 (9) | 0.054 (3)* | 0.5 |
H37 | 0.6314 | −0.1010 | 0.7600 | 0.065* | 0.5 |
C38 | 0.5507 (7) | −0.0856 (6) | 0.6874 (10) | 0.071 (4)* | 0.5 |
C39 | 0.5090 (7) | −0.1163 (6) | 0.6309 (10) | 0.063 (4)* | 0.5 |
H39 | 0.4745 | −0.0925 | 0.6015 | 0.076* | 0.5 |
C40 | 0.5186 (7) | −0.1851 (5) | 0.6172 (9) | 0.052 (4)* | 0.5 |
H40 | 0.4886 | −0.2070 | 0.5782 | 0.062* | 0.5 |
C41 | 0.5766 (2) | 0.67179 (19) | 0.8582 (3) | 0.0286 (11) | |
C42 | 0.6429 (2) | 0.67537 (18) | 0.9037 (3) | 0.0260 (9) | |
C43 | 0.6469 (3) | 0.6791 (2) | 0.9952 (3) | 0.0380 (11) | |
H43 | 0.6069 | 0.6816 | 1.0289 | 0.046* | |
C44 | 0.7073 (3) | 0.6794 (2) | 1.0380 (3) | 0.0410 (12) | |
H44 | 0.7088 | 0.6828 | 1.1005 | 0.049* | |
C45 | 0.7657 (2) | 0.67477 (19) | 0.9908 (4) | 0.0361 (11) | |
C46 | 0.7626 (2) | 0.6705 (2) | 0.8997 (3) | 0.0361 (11) | |
H46 | 0.8027 | 0.6667 | 0.8666 | 0.043* | |
C47 | 0.7017 (3) | 0.6716 (2) | 0.8560 (3) | 0.0353 (11) | |
H47 | 0.7004 | 0.6697 | 0.7933 | 0.042* | |
C48 | 0.8319 (3) | 0.6726 (2) | 1.0396 (4) | 0.0469 (14) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0203 (3) | 0.0253 (3) | 0.0296 (3) | 0.0000 (2) | 0.0023 (2) | 0.00168 (18) |
O1 | 0.0140 (16) | 0.0446 (18) | 0.048 (2) | −0.0013 (13) | 0.0009 (16) | 0.0029 (14) |
O2 | 0.037 (2) | 0.067 (2) | 0.0299 (17) | 0.0076 (17) | −0.0089 (16) | −0.0097 (15) |
O3 | 0.054 (3) | 0.0392 (19) | 0.063 (2) | 0.0023 (17) | −0.033 (2) | 0.0006 (16) |
O4 | 0.029 (2) | 0.046 (2) | 0.094 (3) | 0.0004 (16) | −0.024 (2) | 0.0005 (19) |
C41 | 0.023 (3) | 0.027 (2) | 0.036 (3) | 0.0016 (18) | −0.008 (2) | −0.0027 (18) |
C42 | 0.018 (2) | 0.025 (2) | 0.035 (2) | −0.0003 (17) | −0.0058 (19) | −0.0030 (17) |
C43 | 0.025 (3) | 0.051 (3) | 0.038 (3) | 0.005 (2) | 0.003 (2) | −0.004 (2) |
C44 | 0.035 (3) | 0.047 (3) | 0.041 (3) | 0.007 (2) | −0.015 (2) | −0.003 (2) |
C45 | 0.024 (3) | 0.027 (2) | 0.057 (3) | −0.0028 (19) | −0.014 (2) | 0.003 (2) |
C46 | 0.023 (3) | 0.033 (2) | 0.053 (3) | 0.0020 (19) | 0.003 (2) | 0.000 (2) |
C47 | 0.026 (3) | 0.048 (3) | 0.032 (2) | −0.004 (2) | 0.000 (2) | 0.000 (2) |
C48 | 0.031 (3) | 0.023 (2) | 0.086 (4) | −0.001 (2) | −0.020 (3) | 0.001 (2) |
Zn1—O1 | 2.008 (3) | C16—C17 | 1.391 (11) |
Zn1—O2i | 2.040 (3) | C17—C18 | 1.366 (12) |
Zn1—O3ii | 2.073 (4) | C18—C19 | 1.341 (12) |
Zn1—N1 | 2.110 (10) | C19—C20 | 1.391 (10) |
Zn1—O4ii | 2.418 (4) | N3—C25 | 1.324 (11) |
Zn1—C48ii | 2.548 (6) | N3—C21 | 1.344 (11) |
O1—C41 | 1.253 (6) | C21—C22 | 1.392 (11) |
O2—C41 | 1.239 (5) | C22—C23 | 1.384 (11) |
O2—Zn1i | 2.040 (3) | C23—C24 | 1.372 (11) |
O3—C48 | 1.259 (7) | C23—C26 | 1.513 (10) |
O3—Zn1iii | 2.073 (4) | C24—C25 | 1.389 (10) |
O4—C48 | 1.237 (7) | C26—C27 | 1.559 (11) |
O4—Zn1iii | 2.418 (4) | C27—C28 | 1.530 (12) |
N1—C5 | 1.336 (11) | C28—C29 | 1.322 (12) |
N1—C1 | 1.344 (11) | C28—C33 | 1.332 (12) |
C1—C2 | 1.382 (10) | C29—C30 | 1.407 (13) |
C2—C3 | 1.378 (11) | C30—C31 | 1.360 (13) |
C3—C4 | 1.381 (11) | C31—C32 | 1.348 (13) |
C3—C6 | 1.501 (9) | C31—C34 | 1.562 (13) |
C4—C5 | 1.395 (10) | C32—C33 | 1.380 (13) |
C6—C7 | 1.565 (11) | C34—C35 | 1.593 (13) |
C6—C26 | 1.591 (10) | C35—C38 | 1.543 (13) |
C7—C8 | 1.521 (11) | N4—C36 | 1.313 (11) |
C7—C27 | 1.603 (11) | N4—C40 | 1.340 (11) |
C8—C13 | 1.313 (11) | C36—C37 | 1.367 (10) |
C8—C9 | 1.316 (11) | C37—C38 | 1.341 (12) |
C9—C10 | 1.373 (11) | C38—C39 | 1.343 (12) |
C10—C11 | 1.347 (12) | C39—C40 | 1.406 (11) |
C11—C12 | 1.369 (12) | C41—C42 | 1.497 (6) |
C11—C14 | 1.547 (13) | C42—C47 | 1.384 (7) |
C12—C13 | 1.391 (12) | C42—C43 | 1.390 (6) |
C14—C15 | 1.590 (14) | C43—C44 | 1.373 (7) |
C14—C34 | 1.615 (13) | C44—C45 | 1.374 (8) |
C15—C18 | 1.552 (13) | C45—C46 | 1.383 (7) |
C15—C35 | 1.613 (13) | C45—C48 | 1.518 (7) |
N2—C16 | 1.313 (11) | C46—C47 | 1.389 (7) |
N2—C20 | 1.328 (10) | C48—Zn1iii | 2.548 (6) |
O1—Zn1—O2i | 116.53 (14) | N2—C20—C19 | 123.2 (10) |
O1—Zn1—O3ii | 150.21 (16) | C25—N3—C21 | 117.9 (11) |
O2i—Zn1—O3ii | 93.19 (16) | N3—C21—C22 | 121.7 (11) |
O1—Zn1—N1 | 87.9 (3) | C23—C22—C21 | 120.6 (10) |
O2i—Zn1—N1 | 90.0 (3) | C24—C23—C22 | 116.4 (8) |
O3ii—Zn1—N1 | 94.4 (3) | C24—C23—C26 | 123.1 (9) |
O1—Zn1—O4ii | 92.18 (15) | C22—C23—C26 | 120.0 (9) |
O2i—Zn1—O4ii | 151.26 (15) | C23—C24—C25 | 120.5 (10) |
O3ii—Zn1—O4ii | 58.07 (16) | N3—C25—C24 | 122.6 (11) |
N1—Zn1—O4ii | 92.4 (3) | C23—C26—C27 | 121.3 (9) |
O1—Zn1—C48ii | 120.85 (18) | C23—C26—C6 | 115.0 (8) |
O2i—Zn1—C48ii | 122.58 (19) | C27—C26—C6 | 90.5 (6) |
O3ii—Zn1—C48ii | 29.39 (18) | C28—C27—C26 | 120.3 (9) |
N1—Zn1—C48ii | 94.1 (4) | C28—C27—C7 | 113.8 (9) |
O4ii—Zn1—C48ii | 28.68 (17) | C26—C27—C7 | 89.8 (5) |
C41—O1—Zn1 | 122.7 (3) | C29—C28—C33 | 116.5 (12) |
C41—O2—Zn1i | 175.5 (4) | C29—C28—C27 | 127.0 (12) |
C48—O3—Zn1iii | 96.7 (4) | C33—C28—C27 | 113.9 (11) |
C48—O4—Zn1iii | 81.5 (4) | C28—C29—C30 | 119.9 (14) |
C5—N1—C1 | 114.5 (10) | C31—C30—C29 | 122.5 (15) |
C5—N1—Zn1 | 123.7 (8) | C32—C31—C30 | 113.0 (14) |
C1—N1—Zn1 | 121.7 (8) | C32—C31—C34 | 110.8 (14) |
N1—C1—C2 | 124.5 (11) | C30—C31—C34 | 134.3 (15) |
C3—C2—C1 | 119.7 (9) | C31—C32—C33 | 120.5 (14) |
C2—C3—C4 | 116.8 (7) | C28—C33—C32 | 123.4 (13) |
C2—C3—C6 | 115.4 (8) | C31—C34—C35 | 113.0 (13) |
C4—C3—C6 | 127.3 (9) | C31—C34—C14 | 117.0 (14) |
C3—C4—C5 | 119.3 (9) | C35—C34—C14 | 90.0 (6) |
N1—C5—C4 | 124.4 (11) | C38—C35—C34 | 120.9 (14) |
C3—C6—C7 | 117.6 (9) | C38—C35—C15 | 117.3 (14) |
C3—C6—C26 | 113.3 (8) | C34—C35—C15 | 89.8 (6) |
C7—C6—C26 | 90.0 (6) | C36—N4—C40 | 114.4 (10) |
C8—C7—C6 | 119.5 (8) | N4—C36—C37 | 122.6 (10) |
C8—C7—C27 | 116.9 (8) | C38—C37—C36 | 122.8 (11) |
C6—C7—C27 | 89.8 (5) | C37—C38—C39 | 117.4 (10) |
C13—C8—C9 | 116.0 (10) | C37—C38—C35 | 119.2 (11) |
C13—C8—C7 | 120.3 (9) | C39—C38—C35 | 121.4 (12) |
C9—C8—C7 | 121.2 (9) | C38—C39—C40 | 117.1 (11) |
C8—C9—C10 | 125.3 (10) | N4—C40—C39 | 125.6 (12) |
C11—C10—C9 | 118.6 (11) | O2—C41—O1 | 125.3 (4) |
C10—C11—C12 | 115.0 (11) | O2—C41—C42 | 117.9 (4) |
C10—C11—C14 | 119.7 (12) | O1—C41—C42 | 116.8 (4) |
C12—C11—C14 | 121.6 (11) | C47—C42—C43 | 118.3 (4) |
C11—C12—C13 | 121.7 (11) | C47—C42—C41 | 120.7 (4) |
C8—C13—C12 | 120.8 (11) | C43—C42—C41 | 120.9 (4) |
C11—C14—C15 | 124.7 (13) | C44—C43—C42 | 121.4 (5) |
C11—C14—C34 | 117.6 (14) | C43—C44—C45 | 120.3 (4) |
C15—C14—C34 | 89.9 (6) | C44—C45—C46 | 118.9 (4) |
C18—C15—C14 | 114.4 (14) | C44—C45—C48 | 119.5 (5) |
C18—C15—C35 | 120.1 (14) | C46—C45—C48 | 121.6 (5) |
C14—C15—C35 | 90.2 (7) | C45—C46—C47 | 121.0 (5) |
C16—N2—C20 | 115.8 (9) | C42—C47—C46 | 119.9 (4) |
N2—C16—C17 | 124.8 (11) | O4—C48—O3 | 123.7 (5) |
C18—C17—C16 | 116.8 (12) | O4—C48—C45 | 118.6 (6) |
C19—C18—C17 | 119.4 (10) | O3—C48—C45 | 117.7 (5) |
C19—C18—C15 | 112.6 (11) | O4—C48—Zn1iii | 69.8 (3) |
C17—C18—C15 | 126.5 (12) | O3—C48—Zn1iii | 53.9 (3) |
C18—C19—C20 | 118.6 (10) | C45—C48—Zn1iii | 171.6 (5) |
Symmetry codes: (i) −x+1, y, −z+3/2; (ii) x−1/2, y, −z+2; (iii) x+1/2, y, −z+2. |
Funding information
Funding for this research was provided by: Ministry of Education - Singapore (National University of Singapore Tier 1 grant No. R-143-000-678-114 to Jagadese J. Vittal); National Research Foundation of Korea (NRF) (grant No. 2016R1A2A2A05918799 to Shim Sung Lee; award No. 2017R1A4A1014595 to Shim Sung Lee).
References
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