| Literature DB >> 21201646 |
Aida Khalighi, Roya Ahmadi, Vahid Amani, Hamid Reza Khavasi.
Abstract
The asymmetric unit of the title compound, [ZnCl(2)(C(12)H(12)N(2))], contains two independent mol-ecules. The Zn(II) atoms are four-coordinated in distorted tetra-hedral configurations by two N atoms from 5,5'-dimethyl-2,2'-bipyridine and two terminal Cl atoms. In the crystal structure, inter-molecular C-H⋯Cl hydrogen bonds link the mol-ecules. There are C-H⋯π contacts between the methyl groups and the pyridine and five-membered rings containing Zn(II) atoms; π-π contacts also exist between the pyridine rings [centroid-centroid distances = 3.665 (5) and 3.674 (5) Å].Entities:
Year: 2008 PMID: 21201646 PMCID: PMC2960607 DOI: 10.1107/S1600536808027104
Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN: 1600-5368
| [ZnCl2(C12H12N2)] | |
| Orthorhombic, | Mo |
| Hall symbol: P 2c -2n | Cell parameters from 2610 reflections |
| θ = 2.2–29.3º | |
| µ = 2.18 mm−1 | |
| Block, colorless | |
| 0.28 × 0.20 × 0.07 mm |
| Bruker SMART CCD area-detector diffractometer | 7167 independent reflections |
| Radiation source: fine-focus sealed tube | 4463 reflections with |
| Monochromator: graphite | |
| θmax = 29.3º | |
| φ and ω scans | θmin = 2.2º |
| Absorption correction: multi-scan(SADABS; Sheldrick, 1998) | |
| 14309 measured reflections |
| Refinement on | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| | |
| (Δ/σ)max = 0.045 | |
| Δρmax = 0.29 e Å−3 | |
| 7167 reflections | Δρmin = −0.30 e Å−3 |
| 307 parameters | Extinction correction: none |
| 1 restraint | Absolute structure: Flack (1983), 3320 Friedel pairs |
| Primary atom site location: structure-invariant direct methods | Flack parameter: 0.07 (3) |
| Secondary atom site location: difference Fourier map |
| Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
| Refinement. Refinement of |
| Zn1 | −0.27268 (5) | −0.87606 (8) | −0.43784 (5) | 0.0530 (4) | |
| Zn2 | −0.77530 (5) | −1.11325 (7) | −0.47118 (5) | 0.0521 (3) | |
| Cl1 | −0.33658 (15) | −0.9839 (2) | −0.33543 (19) | 0.0872 (8) | |
| Cl2 | −0.35350 (12) | −0.7899 (2) | −0.53825 (16) | 0.0671 (6) | |
| Cl3 | −0.84859 (13) | −1.0208 (2) | −0.36748 (16) | 0.0644 (6) | |
| Cl4 | −0.84271 (14) | −1.2264 (2) | −0.56774 (19) | 0.0823 (8) | |
| N1 | −0.1798 (4) | −0.7734 (5) | −0.3840 (4) | 0.0508 (16) | |
| N2 | −0.1730 (4) | −0.9564 (5) | −0.4975 (4) | 0.0508 (15) | |
| N3 | −0.6710 (4) | −1.1912 (5) | −0.4188 (4) | 0.0521 (14) | |
| N4 | −0.6855 (4) | −1.0095 (6) | −0.5312 (5) | 0.0503 (15) | |
| C1 | −0.1882 (5) | −0.6828 (7) | −0.3260 (5) | 0.0541 (18) | |
| H1 | −0.2408 | −0.6608 | −0.3081 | 0.065* | |
| C2 | −0.1206 (6) | −0.6198 (7) | −0.2909 (6) | 0.060 (2) | |
| C3 | −0.1361 (7) | −0.5168 (8) | −0.2285 (6) | 0.089 (3) | |
| H3A | −0.1689 | −0.4576 | −0.2584 | 0.107* | |
| H3B | −0.0846 | −0.4819 | −0.2108 | 0.107* | |
| H3C | −0.1648 | −0.5449 | −0.1764 | 0.107* | |
| C4 | −0.0441 (6) | −0.6540 (9) | −0.3175 (6) | 0.071 (2) | |
| H4 | 0.0018 | −0.6146 | −0.2949 | 0.085* | |
| C5 | −0.0340 (5) | −0.7457 (9) | −0.3773 (6) | 0.062 (2) | |
| H5 | 0.0183 | −0.7674 | −0.3963 | 0.075* | |
| C6 | −0.1031 (5) | −0.8063 (7) | −0.4095 (5) | 0.0524 (19) | |
| C7 | −0.1007 (4) | −0.9082 (7) | −0.4741 (6) | 0.0459 (17) | |
| C8 | −0.0275 (5) | −0.9510 (8) | −0.5090 (5) | 0.061 (2) | |
| H8 | 0.0226 | −0.9168 | −0.4930 | 0.073* | |
| C9 | −0.0309 (5) | −1.0467 (9) | −0.5686 (6) | 0.069 (3) | |
| H9 | 0.0177 | −1.0773 | −0.5921 | 0.082* | |
| C10 | −0.1045 (7) | −1.0967 (8) | −0.5934 (6) | 0.062 (3) | |
| C11 | −0.1117 (7) | −1.1986 (8) | −0.6598 (6) | 0.082 (3) | |
| H11A | −0.1368 | −1.2664 | −0.6311 | 0.098* | |
| H11B | −0.0579 | −1.2202 | −0.6807 | 0.098* | |
| H11C | −0.1449 | −1.1739 | −0.7096 | 0.098* | |
| C12 | −0.1746 (5) | −1.0486 (7) | −0.5547 (6) | 0.057 (2) | |
| H12 | −0.2252 | −1.0820 | −0.5694 | 0.068* | |
| C13 | −0.6682 (5) | −1.2826 (7) | −0.3606 (6) | 0.059 (2) | |
| H13 | −0.7178 | −1.3166 | −0.3429 | 0.071* | |
| C14 | −0.5966 (6) | −1.3302 (9) | −0.3250 (6) | 0.067 (2) | |
| C15 | −0.5985 (7) | −1.4306 (9) | −0.2602 (6) | 0.089 (3) | |
| H15A | −0.6285 | −1.4068 | −0.2078 | 0.107* | |
| H15B | −0.5434 | −1.4516 | −0.2438 | 0.107* | |
| H15C | −0.6251 | −1.4985 | −0.2871 | 0.107* | |
| C16 | −0.5243 (6) | −1.2783 (9) | −0.3560 (7) | 0.074 (3) | |
| H16 | −0.4741 | −1.3087 | −0.3370 | 0.089* | |
| C17 | −0.5255 (5) | −1.1830 (9) | −0.4141 (6) | 0.074 (2) | |
| H17 | −0.4765 | −1.1473 | −0.4322 | 0.089* | |
| C18 | −0.6005 (5) | −1.1398 (8) | −0.4458 (7) | 0.0552 (19) | |
| C19 | −0.6087 (4) | −1.0390 (7) | −0.5074 (5) | 0.0501 (17) | |
| C20 | −0.5433 (5) | −0.9743 (9) | −0.5441 (7) | 0.072 (3) | |
| H20 | −0.4894 | −0.9962 | −0.5310 | 0.086* | |
| C21 | −0.5580 (6) | −0.8791 (8) | −0.5990 (5) | 0.069 (2) | |
| H21 | −0.5140 | −0.8339 | −0.6199 | 0.083* | |
| C22 | −0.6369 (6) | −0.8486 (7) | −0.6240 (5) | 0.0578 (19) | |
| C23 | −0.6548 (6) | −0.7477 (8) | −0.6847 (6) | 0.080 (3) | |
| H23A | −0.6848 | −0.7765 | −0.7357 | 0.096* | |
| H23B | −0.6042 | −0.7120 | −0.7042 | 0.096* | |
| H23C | −0.6871 | −0.6891 | −0.6536 | 0.096* | |
| C24 | −0.6992 (5) | −0.9174 (7) | −0.5874 (5) | 0.0572 (18) | |
| H24 | −0.7533 | −0.8990 | −0.6023 | 0.069* |
| Zn1 | 0.0310 (4) | 0.0557 (5) | 0.0721 (10) | −0.0013 (4) | 0.0036 (4) | 0.0035 (4) |
| Zn2 | 0.0336 (4) | 0.0550 (5) | 0.0678 (9) | 0.0005 (4) | −0.0026 (4) | −0.0006 (4) |
| Cl1 | 0.0615 (14) | 0.0871 (16) | 0.113 (2) | 0.0035 (12) | 0.0292 (13) | 0.0328 (14) |
| Cl2 | 0.0426 (10) | 0.0783 (13) | 0.0805 (15) | 0.0030 (9) | −0.0096 (9) | 0.0048 (11) |
| Cl3 | 0.0490 (11) | 0.0682 (12) | 0.0759 (14) | −0.0025 (9) | 0.0060 (9) | −0.0081 (10) |
| Cl4 | 0.0550 (13) | 0.0829 (15) | 0.109 (2) | 0.0089 (11) | −0.0215 (12) | −0.0355 (14) |
| N1 | 0.038 (3) | 0.049 (3) | 0.065 (4) | −0.002 (3) | −0.007 (3) | 0.012 (3) |
| N2 | 0.037 (3) | 0.047 (3) | 0.069 (4) | −0.003 (3) | 0.011 (3) | 0.009 (3) |
| N3 | 0.041 (3) | 0.057 (3) | 0.058 (4) | −0.001 (3) | −0.001 (3) | −0.011 (3) |
| N4 | 0.034 (3) | 0.063 (4) | 0.055 (4) | −0.002 (3) | 0.003 (3) | −0.008 (3) |
| C1 | 0.045 (4) | 0.057 (4) | 0.061 (4) | −0.002 (3) | −0.008 (3) | 0.002 (3) |
| C2 | 0.065 (5) | 0.062 (5) | 0.053 (5) | −0.006 (4) | −0.016 (4) | 0.013 (4) |
| C3 | 0.135 (10) | 0.068 (6) | 0.066 (6) | −0.018 (6) | −0.023 (6) | 0.001 (4) |
| C4 | 0.067 (6) | 0.080 (6) | 0.066 (5) | −0.028 (5) | −0.016 (4) | 0.006 (5) |
| C5 | 0.035 (4) | 0.088 (6) | 0.063 (5) | −0.004 (4) | −0.002 (3) | 0.010 (5) |
| C6 | 0.046 (4) | 0.058 (4) | 0.054 (4) | −0.010 (3) | −0.005 (3) | 0.021 (3) |
| C7 | 0.027 (3) | 0.056 (4) | 0.055 (5) | 0.003 (3) | 0.007 (3) | 0.017 (4) |
| C8 | 0.046 (4) | 0.073 (5) | 0.065 (5) | 0.012 (4) | 0.008 (3) | 0.014 (4) |
| C9 | 0.051 (5) | 0.093 (7) | 0.062 (5) | 0.025 (5) | 0.021 (4) | 0.027 (5) |
| C10 | 0.081 (7) | 0.057 (4) | 0.048 (5) | 0.023 (5) | 0.013 (4) | 0.022 (4) |
| C11 | 0.102 (8) | 0.073 (6) | 0.071 (6) | 0.026 (5) | 0.017 (5) | 0.005 (5) |
| C12 | 0.041 (4) | 0.059 (5) | 0.071 (5) | −0.002 (3) | 0.000 (3) | 0.017 (4) |
| C13 | 0.058 (5) | 0.056 (5) | 0.064 (5) | 0.001 (4) | −0.009 (4) | −0.008 (4) |
| C14 | 0.069 (6) | 0.070 (5) | 0.061 (5) | 0.029 (5) | −0.013 (4) | −0.019 (4) |
| C15 | 0.112 (9) | 0.082 (7) | 0.073 (6) | 0.028 (6) | −0.029 (6) | −0.006 (5) |
| C16 | 0.052 (5) | 0.093 (7) | 0.078 (6) | 0.032 (5) | −0.014 (4) | −0.013 (5) |
| C17 | 0.037 (4) | 0.098 (7) | 0.089 (6) | 0.006 (4) | −0.012 (4) | −0.016 (5) |
| C18 | 0.048 (4) | 0.059 (4) | 0.058 (5) | 0.008 (4) | 0.010 (4) | −0.020 (4) |
| C19 | 0.033 (3) | 0.068 (4) | 0.049 (4) | 0.001 (3) | 0.002 (3) | −0.018 (3) |
| C20 | 0.039 (4) | 0.098 (7) | 0.078 (6) | −0.011 (4) | 0.005 (4) | −0.032 (5) |
| C21 | 0.078 (6) | 0.076 (6) | 0.053 (5) | −0.021 (5) | 0.005 (4) | −0.006 (4) |
| C22 | 0.077 (6) | 0.054 (4) | 0.042 (4) | −0.005 (4) | 0.008 (3) | −0.008 (3) |
| C23 | 0.093 (7) | 0.076 (6) | 0.071 (6) | −0.018 (5) | 0.013 (5) | −0.007 (5) |
| C24 | 0.050 (4) | 0.066 (5) | 0.055 (4) | 0.005 (4) | 0.002 (3) | −0.002 (4) |
| Zn1—Cl1 | 2.206 (2) | C11—H11B | 0.9600 |
| Zn1—Cl2 | 2.215 (2) | C11—H11C | 0.9600 |
| Zn2—Cl3 | 2.211 (2) | C12—N2 | 1.338 (10) |
| Zn2—Cl4 | 2.207 (3) | C12—H12 | 0.9300 |
| Zn1—N1 | 2.058 (6) | C13—N3 | 1.341 (10) |
| Zn1—N2 | 2.057 (6) | C13—C14 | 1.386 (11) |
| Zn2—N3 | 2.063 (6) | C13—H13 | 0.9300 |
| Zn2—N4 | 2.066 (6) | C14—C16 | 1.389 (13) |
| C1—N1 | 1.339 (10) | C14—C15 | 1.482 (13) |
| C1—C2 | 1.406 (12) | C15—H15A | 0.9600 |
| C1—H1 | 0.9300 | C15—H15B | 0.9600 |
| C2—C4 | 1.362 (14) | C15—H15C | 0.9600 |
| C2—C3 | 1.502 (12) | C16—C17 | 1.374 (13) |
| C3—H3A | 0.9600 | C16—H16 | 0.9300 |
| C3—H3B | 0.9600 | C17—C18 | 1.397 (11) |
| C3—H3C | 0.9600 | C17—H17 | 0.9300 |
| C4—C5 | 1.369 (13) | C18—N3 | 1.343 (10) |
| C4—H4 | 0.9300 | C18—C19 | 1.460 (12) |
| C5—C6 | 1.396 (11) | C19—N4 | 1.341 (9) |
| C5—H5 | 0.9300 | C19—C20 | 1.397 (11) |
| C6—N1 | 1.357 (10) | C20—C21 | 1.364 (13) |
| C6—C7 | 1.491 (11) | C20—H20 | 0.9300 |
| C7—N2 | 1.339 (9) | C21—C22 | 1.379 (14) |
| C7—C8 | 1.387 (10) | C21—H21 | 0.9300 |
| C8—C9 | 1.392 (12) | C22—C24 | 1.384 (12) |
| C8—H8 | 0.9300 | C22—C23 | 1.476 (12) |
| C9—C10 | 1.372 (14) | C23—H23A | 0.9600 |
| C9—H9 | 0.9300 | C23—H23B | 0.9600 |
| C10—C12 | 1.386 (13) | C23—H23C | 0.9600 |
| C10—C11 | 1.514 (13) | C24—N4 | 1.348 (10) |
| C11—H11A | 0.9600 | C24—H24 | 0.9300 |
| N1—Zn1—N2 | 80.5 (2) | N3—C13—C14 | 124.8 (8) |
| N1—Zn1—Cl1 | 112.2 (2) | N3—C13—H13 | 117.6 |
| N1—Zn1—Cl2 | 117.23 (18) | C14—C13—H13 | 117.6 |
| N2—Zn1—Cl1 | 115.64 (18) | C13—C14—C16 | 115.0 (9) |
| N2—Zn1—Cl2 | 111.4 (2) | C13—C14—C15 | 121.6 (9) |
| Cl1—Zn1—Cl2 | 115.28 (10) | C16—C14—C15 | 123.4 (9) |
| N3—Zn2—N4 | 79.7 (3) | C14—C15—H15A | 109.4 |
| N3—Zn2—Cl3 | 112.09 (18) | C14—C15—H15B | 109.5 |
| N3—Zn2—Cl4 | 114.47 (17) | H15A—C15—H15B | 109.5 |
| N4—Zn2—Cl4 | 112.8 (2) | C14—C15—H15C | 109.5 |
| N4—Zn2—Cl3 | 115.01 (18) | H15A—C15—H15C | 109.5 |
| Cl4—Zn2—Cl3 | 117.19 (9) | H15B—C15—H15C | 109.5 |
| N1—C1—C2 | 122.6 (8) | C17—C16—C14 | 121.4 (8) |
| N1—C1—H1 | 118.7 | C17—C16—H16 | 119.3 |
| C2—C1—H1 | 118.7 | C14—C16—H16 | 119.3 |
| C4—C2—C1 | 117.7 (8) | C16—C17—C18 | 119.6 (9) |
| C4—C2—C3 | 123.4 (9) | C16—C17—H17 | 120.2 |
| C1—C2—C3 | 118.9 (9) | C18—C17—H17 | 120.2 |
| C2—C3—H3A | 109.5 | N3—C18—C17 | 119.7 (9) |
| C2—C3—H3B | 109.5 | N3—C18—C19 | 116.2 (7) |
| H3A—C3—H3B | 109.5 | C17—C18—C19 | 124.1 (8) |
| C2—C3—H3C | 109.5 | N4—C19—C20 | 118.6 (8) |
| H3A—C3—H3C | 109.5 | N4—C19—C18 | 116.2 (7) |
| H3B—C3—H3C | 109.5 | C20—C19—C18 | 125.2 (8) |
| C2—C4—C5 | 120.8 (8) | C21—C20—C19 | 120.3 (9) |
| C2—C4—H4 | 119.6 | C21—C20—H20 | 119.9 |
| C5—C4—H4 | 119.6 | C19—C20—H20 | 119.9 |
| C4—C5—C6 | 119.4 (8) | C20—C21—C22 | 121.4 (9) |
| C4—C5—H5 | 120.3 | C20—C21—H21 | 119.3 |
| C6—C5—H5 | 120.3 | C22—C21—H21 | 119.3 |
| N1—C6—C5 | 120.8 (8) | C21—C22—C24 | 115.9 (8) |
| N1—C6—C7 | 114.4 (7) | C21—C22—C23 | 122.7 (9) |
| C5—C6—C7 | 124.8 (8) | C24—C22—C23 | 121.3 (9) |
| N2—C7—C8 | 121.1 (8) | C22—C23—H23A | 109.5 |
| N2—C7—C6 | 116.9 (7) | C22—C23—H23B | 109.5 |
| C8—C7—C6 | 122.0 (8) | H23A—C23—H23B | 109.5 |
| C7—C8—C9 | 118.2 (8) | C22—C23—H23C | 109.5 |
| C7—C8—H8 | 120.9 | H23A—C23—H23C | 109.5 |
| C9—C8—H8 | 120.9 | H23B—C23—H23C | 109.5 |
| C10—C9—C8 | 121.3 (8) | N4—C24—C22 | 123.2 (8) |
| C10—C9—H9 | 119.4 | N4—C24—H24 | 118.4 |
| C8—C9—H9 | 119.4 | C22—C24—H24 | 118.4 |
| C9—C10—C12 | 116.6 (9) | C1—N1—C6 | 118.8 (7) |
| C9—C10—C11 | 123.3 (9) | C1—N1—Zn1 | 126.7 (5) |
| C12—C10—C11 | 120.2 (10) | C6—N1—Zn1 | 114.5 (5) |
| C10—C11—H11A | 109.4 | C12—N2—C7 | 119.4 (7) |
| C10—C11—H11B | 109.5 | C12—N2—Zn1 | 126.8 (5) |
| H11A—C11—H11B | 109.5 | C7—N2—Zn1 | 113.8 (5) |
| C10—C11—H11C | 109.5 | C13—N3—C18 | 119.4 (7) |
| H11A—C11—H11C | 109.5 | C13—N3—Zn2 | 126.6 (5) |
| H11B—C11—H11C | 109.5 | C18—N3—Zn2 | 114.0 (6) |
| N2—C12—C10 | 123.4 (8) | C19—N4—C24 | 120.5 (7) |
| N2—C12—H12 | 118.3 | C19—N4—Zn2 | 114.0 (5) |
| C10—C12—H12 | 118.3 | C24—N4—Zn2 | 125.5 (5) |
| N1—C1—C2—C4 | −0.3 (13) | N2—Zn1—N1—C1 | −179.1 (6) |
| N1—C1—C2—C3 | 177.9 (7) | Cl1—Zn1—N1—C1 | −65.2 (7) |
| C1—C2—C4—C5 | 0.8 (13) | Cl2—Zn1—N1—C1 | 71.6 (7) |
| C3—C2—C4—C5 | −177.4 (9) | N2—Zn1—N1—C6 | −1.4 (5) |
| C2—C4—C5—C6 | −1.5 (14) | Cl1—Zn1—N1—C6 | 112.5 (5) |
| C4—C5—C6—N1 | 1.7 (12) | Cl2—Zn1—N1—C6 | −110.7 (5) |
| C4—C5—C6—C7 | −179.5 (8) | C10—C12—N2—C7 | −1.2 (12) |
| N1—C6—C7—N2 | −1.5 (9) | C10—C12—N2—Zn1 | 178.9 (6) |
| C5—C6—C7—N2 | 179.6 (8) | C8—C7—N2—C12 | 0.8 (12) |
| N1—C6—C7—C8 | 178.1 (7) | C6—C7—N2—C12 | −179.6 (6) |
| C5—C6—C7—C8 | −0.8 (11) | C8—C7—N2—Zn1 | −179.3 (6) |
| N2—C7—C8—C9 | −0.6 (12) | C6—C7—N2—Zn1 | 0.3 (9) |
| C6—C7—C8—C9 | 179.8 (7) | N1—Zn1—N2—C12 | −179.6 (7) |
| C7—C8—C9—C10 | 0.8 (13) | Cl1—Zn1—N2—C12 | 70.3 (7) |
| C8—C9—C10—C12 | −1.2 (12) | Cl2—Zn1—N2—C12 | −64.0 (7) |
| C8—C9—C10—C11 | 178.3 (8) | N1—Zn1—N2—C7 | 0.5 (6) |
| C9—C10—C12—N2 | 1.4 (12) | Cl1—Zn1—N2—C7 | −109.6 (5) |
| C11—C10—C12—N2 | −178.1 (8) | Cl2—Zn1—N2—C7 | 116.2 (6) |
| N3—C13—C14—C16 | −1.8 (12) | C14—C13—N3—C18 | −0.1 (12) |
| N3—C13—C14—C15 | 179.3 (8) | C14—C13—N3—Zn2 | −178.1 (6) |
| C13—C14—C16—C17 | 3.1 (13) | C17—C18—N3—C13 | 0.8 (13) |
| C15—C14—C16—C17 | −178.1 (9) | C19—C18—N3—C13 | −178.5 (7) |
| C14—C16—C17—C18 | −2.6 (15) | C17—C18—N3—Zn2 | 179.0 (7) |
| C16—C17—C18—N3 | 0.5 (15) | C19—C18—N3—Zn2 | −0.3 (10) |
| C16—C17—C18—C19 | 179.8 (8) | N4—Zn2—N3—C13 | 178.9 (7) |
| N3—C18—C19—N4 | −0.8 (11) | Cl4—Zn2—N3—C13 | −70.6 (7) |
| C17—C18—C19—N4 | 179.9 (8) | Cl3—Zn2—N3—C13 | 66.0 (6) |
| N3—C18—C19—C20 | −179.3 (7) | N4—Zn2—N3—C18 | 0.8 (6) |
| C17—C18—C19—C20 | 1.4 (14) | Cl4—Zn2—N3—C18 | 111.3 (6) |
| N4—C19—C20—C21 | 3.6 (12) | Cl3—Zn2—N3—C18 | −112.1 (6) |
| C18—C19—C20—C21 | −178.0 (8) | C20—C19—N4—C24 | −1.7 (10) |
| C19—C20—C21—C22 | −4.0 (13) | C18—C19—N4—C24 | 179.7 (7) |
| C20—C21—C22—C24 | 2.4 (12) | C20—C19—N4—Zn2 | −179.9 (6) |
| C20—C21—C22—C23 | −178.8 (8) | C18—C19—N4—Zn2 | 1.5 (8) |
| C21—C22—C24—N4 | −0.5 (11) | C22—C24—N4—C19 | 0.3 (11) |
| C23—C22—C24—N4 | −179.4 (7) | C22—C24—N4—Zn2 | 178.3 (5) |
| C2—C1—N1—C6 | 0.5 (11) | N3—Zn2—N4—C19 | −1.3 (5) |
| C2—C1—N1—Zn1 | 178.2 (6) | Cl4—Zn2—N4—C19 | −113.6 (5) |
| C5—C6—N1—C1 | −1.2 (10) | Cl3—Zn2—N4—C19 | 108.4 (5) |
| C7—C6—N1—C1 | 179.8 (6) | N3—Zn2—N4—C24 | −179.4 (6) |
| C5—C6—N1—Zn1 | −179.1 (6) | Cl4—Zn2—N4—C24 | 68.3 (6) |
| C7—C6—N1—Zn1 | 1.9 (7) | Cl3—Zn2—N4—C24 | −69.7 (6) |
| H··· | ||||
| C1—H1···Cl3i | 0.93 | 2.82 | 3.516 (8) | 132 |
| C16—H16···Cl3ii | 0.93 | 2.83 | 3.638 (10) | 146 |
| C3—H3A···Cg5 | 0.96 | 3.10 | 3.719 (6) | 124 |
| C11—H11A···Cg2iii | 0.96 | 2.83 | 3.688 (5) | 150 |
| C15—H15C···Cg1iv | 0.96 | 2.84 | 3.704 (6) | 150 |
| C23—H23C···Cg4 | 0.96 | 3.11 | 3.690 (6) | 120 |
| Zn1—Cl1 | 2.206 (2) |
| Zn1—Cl2 | 2.215 (2) |
| Zn2—Cl3 | 2.211 (2) |
| Zn2—Cl4 | 2.207 (3) |
| Zn1—N1 | 2.058 (6) |
| Zn1—N2 | 2.057 (6) |
| Zn2—N3 | 2.063 (6) |
| Zn2—N4 | 2.066 (6) |
| N1—Zn1—N2 | 80.5 (2) |
| N1—Zn1—Cl1 | 112.2 (2) |
| N1—Zn1—Cl2 | 117.23 (18) |
| N2—Zn1—Cl1 | 115.64 (18) |
| N2—Zn1—Cl2 | 111.4 (2) |
| Cl1—Zn1—Cl2 | 115.28 (10) |
| N3—Zn2—N4 | 79.7 (3) |
| N3—Zn2—Cl3 | 112.09 (18) |
| N3—Zn2—Cl4 | 114.47 (17) |
| N4—Zn2—Cl4 | 112.8 (2) |
| N4—Zn2—Cl3 | 115.01 (18) |
| Cl4—Zn2—Cl3 | 117.19 (9) |
Hydrogen-bond geometry (Å, °)
| H⋯ | ||||
|---|---|---|---|---|
| C1—H1⋯Cl3i | 0.93 | 2.82 | 3.516 (8) | 132 |
| C16—H16⋯Cl3ii | 0.93 | 2.83 | 3.638 (10) | 146 |
| C3—H3 | 0.96 | 3.10 | 3.719 (6) | 124 |
| C11—H11 | 0.96 | 2.83 | 3.688 (5) | 150 |
| C15—H15 | 0.96 | 2.84 | 3.704 (6) | 150 |
| C23—H23 | 0.96 | 3.11 | 3.690 (6) | 120 |
Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1, Cg2, Cg4 and Cg5 are the centroids of atoms Zn1/N1/C6/C7/N2, N1/C1/C2/C4–C6, Zn2/N3/C18/C19/N4 and N3/C13/C14/C16–C18, respectively.