metal-organic compounds
The title compound, [Zn2(C13H9ClN2O2S)2(C5H5N)2], is dimeric via Zn—O bridges with an average Zn—O distance of 2.027 Å. The ZnZn separation is 3.1003 (5) Å and the geometry of both Zn atoms is square pyramidal.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680302909X/rn6010sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680302909X/rn6010Isup2.hkl |
CCDC reference: 231839
Computing details top
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
Bis{µ-2'-[1-(4-chloro-2-oxidophenyl)ethylidene]thiophene-2-
carbohydrazidato}bis[pyridinezinc(II)] top
Crystal data top
[Zn2(C13H9ClN2O2S)2(C5H5N)2] | F(000) = 1776 |
Mr = 874.40 | Dx = 1.604 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 18.367 (2) Å | Cell parameters from 9860 reflections |
b = 10.201 (2) Å | θ = 1.3–27.6° |
c = 20.242 (2) Å | µ = 1.64 mm−1 |
β = 107.318 (3)° | T = 293 K |
V = 3620.4 (8) Å3 | Block, yellow |
Z = 4 | 0.44 × 0.39 × 0.37 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 8380 independent reflections |
Radiation source: fine-focus sealed tube | 6706 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
Detector resolution: 83.66 pixels mm-1 | θmax = 27.6°, θmin = 1.3° |
ω scans | h = −23→23 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −12→13 |
Tmin = 0.499, Tmax = 0.546 | l = −16→26 |
23971 measured reflections |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.138 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0743P)2 + 2.3755P] where P = (Fo2 + 2Fc2)/3 |
8380 reflections | (Δ/σ)max < 0.001 |
469 parameters | Δρmax = 0.88 e Å−3 |
0 restraints | Δρmin = −0.37 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Zn1 | 0.202037 (18) | 0.61779 (4) | 0.026241 (17) | 0.03929 (11) | |
Zn2 | 0.292618 (17) | 0.83639 (4) | −0.021172 (17) | 0.03882 (11) | |
Cl1 | −0.09678 (5) | 1.06969 (13) | −0.17002 (6) | 0.0798 (3) | |
Cl2 | 0.59505 (6) | 0.40299 (13) | 0.18416 (6) | 0.0785 (3) | |
S1 | 0.05947 (6) | 0.38936 (12) | 0.19664 (6) | 0.0696 (3) | |
S2 | 0.43563 (6) | 1.10851 (11) | −0.17566 (6) | 0.0679 (3) | |
O1 | 0.18304 (10) | 0.7815 (2) | −0.03213 (11) | 0.0432 (5) | |
O2 | 0.21247 (12) | 0.5204 (3) | 0.11380 (12) | 0.0591 (7) | |
O3 | 0.31206 (11) | 0.6715 (2) | 0.03571 (11) | 0.0434 (5) | |
O4 | 0.28321 (12) | 0.9259 (3) | −0.11075 (12) | 0.0584 (6) | |
N1 | 0.09690 (14) | 0.6516 (3) | 0.04059 (13) | 0.0434 (6) | |
N2 | 0.08487 (15) | 0.5719 (3) | 0.09198 (14) | 0.0484 (6) | |
N3 | 0.40132 (13) | 0.8147 (3) | −0.03015 (13) | 0.0415 (5) | |
N4 | 0.41430 (14) | 0.9001 (3) | −0.07913 (13) | 0.0446 (6) | |
N5 | 0.19202 (15) | 0.4732 (3) | −0.04624 (15) | 0.0500 (6) | |
N6 | 0.30584 (15) | 0.9780 (3) | 0.05442 (14) | 0.0470 (6) | |
C1 | 0.11698 (16) | 0.8415 (3) | −0.06269 (15) | 0.0382 (6) | |
C2 | 0.11514 (17) | 0.9329 (3) | −0.11455 (16) | 0.0492 (7) | |
H2B | 0.1595 | 0.9478 | −0.1266 | 0.059* | |
C3 | 0.05079 (18) | 1.0016 (4) | −0.14844 (17) | 0.0528 (8) | |
H3A | 0.0513 | 1.0615 | −0.1829 | 0.063* | |
C4 | −0.01483 (17) | 0.9795 (4) | −0.13010 (17) | 0.0514 (8) | |
C5 | −0.01558 (17) | 0.8908 (3) | −0.08039 (17) | 0.0490 (7) | |
H5A | −0.0608 | 0.8774 | −0.0695 | 0.059* | |
C6 | 0.04925 (16) | 0.8185 (3) | −0.04476 (15) | 0.0407 (6) | |
C7 | 0.04094 (16) | 0.7271 (3) | 0.00854 (16) | 0.0440 (7) | |
C8 | −0.03309 (19) | 0.7214 (4) | 0.0256 (2) | 0.0664 (11) | |
H8A | −0.0295 | 0.6571 | 0.0611 | 0.100* | |
H8B | −0.0734 | 0.6977 | −0.0151 | 0.100* | |
H8C | −0.0437 | 0.8057 | 0.0417 | 0.100* | |
C9 | 0.14757 (17) | 0.5113 (3) | 0.12508 (15) | 0.0433 (7) | |
C10 | 0.14400 (17) | 0.4241 (3) | 0.18152 (15) | 0.0426 (6) | |
C11 | 0.1023 (2) | 0.2885 (4) | 0.2627 (2) | 0.0706 (11) | |
H11A | 0.0762 | 0.2429 | 0.2884 | 0.085* | |
C12 | 0.1776 (2) | 0.2808 (4) | 0.2741 (2) | 0.0681 (11) | |
H12A | 0.2089 | 0.2283 | 0.3086 | 0.082* | |
C13 | 0.2060 (2) | 0.3598 (4) | 0.22912 (17) | 0.0543 (8) | |
H13A | 0.2569 | 0.3678 | 0.2308 | 0.065* | |
C14 | 0.37864 (16) | 0.6158 (3) | 0.06863 (15) | 0.0381 (6) | |
C15 | 0.38027 (17) | 0.5225 (3) | 0.11959 (16) | 0.0450 (7) | |
H15A | 0.3350 | 0.5030 | 0.1292 | 0.054* | |
C16 | 0.44522 (18) | 0.4587 (3) | 0.15592 (16) | 0.0483 (7) | |
H16A | 0.4443 | 0.3973 | 0.1896 | 0.058* | |
C17 | 0.51188 (17) | 0.4873 (4) | 0.14155 (17) | 0.0509 (8) | |
C18 | 0.51378 (17) | 0.5785 (3) | 0.09319 (16) | 0.0480 (7) | |
H18A | 0.5601 | 0.5968 | 0.0853 | 0.058* | |
C19 | 0.44811 (16) | 0.6464 (3) | 0.05461 (15) | 0.0397 (6) | |
C20 | 0.45740 (16) | 0.7407 (3) | 0.00278 (15) | 0.0413 (6) | |
C21 | 0.53262 (18) | 0.7506 (4) | −0.01168 (19) | 0.0580 (9) | |
H21A | 0.5294 | 0.8157 | −0.0467 | 0.087* | |
H21B | 0.5452 | 0.6673 | −0.0275 | 0.087* | |
H21C | 0.5714 | 0.7751 | 0.0299 | 0.087* | |
C22 | 0.34949 (17) | 0.9498 (3) | −0.11676 (15) | 0.0434 (7) | |
C23 | 0.35275 (16) | 1.0431 (3) | −0.17096 (16) | 0.0449 (7) | |
C24 | 0.3905 (3) | 1.2031 (4) | −0.2439 (2) | 0.0700 (11) | |
H24A | 0.4153 | 1.2616 | −0.2651 | 0.084* | |
C25 | 0.3158 (2) | 1.1847 (5) | −0.2639 (2) | 0.0744 (12) | |
H25A | 0.2829 | 1.2307 | −0.3004 | 0.089* | |
C26 | 0.28949 (19) | 1.0874 (4) | −0.22440 (18) | 0.0611 (10) | |
H26A | 0.2394 | 1.0590 | −0.2329 | 0.073* | |
C27 | 0.2355 (3) | 0.3661 (6) | −0.0329 (3) | 0.110 (2) | |
H27A | 0.2700 | 0.3554 | 0.0109 | 0.132* | |
C28 | 0.2305 (4) | 0.2710 (7) | −0.0822 (4) | 0.153 (3) | |
H28A | 0.2618 | 0.1974 | −0.0723 | 0.183* | |
C29 | 0.1783 (4) | 0.2867 (7) | −0.1463 (3) | 0.120 (2) | |
H29A | 0.1754 | 0.2254 | −0.1811 | 0.145* | |
C30 | 0.1314 (3) | 0.3914 (5) | −0.1586 (2) | 0.0899 (16) | |
H30A | 0.0941 | 0.4018 | −0.2010 | 0.108* | |
C31 | 0.1400 (3) | 0.4819 (4) | −0.1070 (2) | 0.0723 (11) | |
H31A | 0.1073 | 0.5537 | −0.1153 | 0.087* | |
C32 | 0.3745 (2) | 1.0175 (4) | 0.0896 (2) | 0.0604 (9) | |
H32A | 0.4156 | 0.9871 | 0.0760 | 0.073* | |
C33 | 0.3893 (2) | 1.1001 (4) | 0.1447 (2) | 0.0756 (12) | |
H33A | 0.4393 | 1.1231 | 0.1681 | 0.091* | |
C34 | 0.3323 (3) | 1.1477 (5) | 0.1650 (3) | 0.0863 (15) | |
H34A | 0.3413 | 1.2078 | 0.2011 | 0.104* | |
C35 | 0.2593 (3) | 1.1057 (6) | 0.1311 (3) | 0.111 (2) | |
H35A | 0.2180 | 1.1341 | 0.1450 | 0.133* | |
C36 | 0.2492 (2) | 1.0216 (5) | 0.0768 (3) | 0.0867 (15) | |
H36A | 0.1999 | 0.9931 | 0.0542 | 0.104* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.03614 (18) | 0.0435 (2) | 0.04098 (19) | 0.00026 (13) | 0.01565 (14) | 0.00075 (13) |
Zn2 | 0.03369 (18) | 0.0439 (2) | 0.04146 (19) | 0.00044 (13) | 0.01514 (14) | 0.00153 (14) |
Cl1 | 0.0503 (5) | 0.1025 (9) | 0.0858 (7) | 0.0305 (5) | 0.0190 (5) | 0.0368 (6) |
Cl2 | 0.0532 (5) | 0.1019 (9) | 0.0715 (6) | 0.0301 (5) | 0.0048 (4) | 0.0213 (6) |
S1 | 0.0565 (5) | 0.0847 (7) | 0.0712 (6) | 0.0013 (5) | 0.0248 (5) | 0.0278 (5) |
S2 | 0.0539 (5) | 0.0804 (7) | 0.0681 (6) | −0.0137 (5) | 0.0163 (4) | 0.0173 (5) |
O1 | 0.0300 (9) | 0.0477 (13) | 0.0523 (12) | 0.0028 (8) | 0.0127 (9) | 0.0098 (9) |
O2 | 0.0392 (11) | 0.0885 (19) | 0.0529 (13) | 0.0045 (12) | 0.0186 (10) | 0.0218 (13) |
O3 | 0.0317 (10) | 0.0469 (12) | 0.0507 (12) | 0.0028 (8) | 0.0110 (9) | 0.0078 (9) |
O4 | 0.0364 (11) | 0.0905 (19) | 0.0495 (13) | −0.0019 (11) | 0.0146 (9) | 0.0187 (12) |
N1 | 0.0423 (13) | 0.0477 (15) | 0.0445 (14) | 0.0015 (11) | 0.0196 (11) | 0.0040 (11) |
N2 | 0.0451 (14) | 0.0524 (16) | 0.0544 (15) | 0.0025 (12) | 0.0252 (12) | 0.0098 (12) |
N3 | 0.0373 (12) | 0.0459 (15) | 0.0434 (13) | 0.0008 (10) | 0.0152 (10) | 0.0000 (11) |
N4 | 0.0403 (13) | 0.0498 (15) | 0.0478 (14) | 0.0006 (11) | 0.0195 (11) | 0.0034 (11) |
N5 | 0.0439 (14) | 0.0494 (16) | 0.0573 (16) | −0.0036 (12) | 0.0161 (12) | −0.0084 (12) |
N6 | 0.0462 (14) | 0.0472 (15) | 0.0515 (15) | −0.0014 (11) | 0.0207 (12) | −0.0053 (12) |
C1 | 0.0329 (13) | 0.0418 (16) | 0.0389 (14) | −0.0006 (11) | 0.0092 (11) | −0.0025 (11) |
C2 | 0.0391 (15) | 0.061 (2) | 0.0498 (18) | 0.0037 (14) | 0.0165 (13) | 0.0090 (15) |
C3 | 0.0456 (17) | 0.061 (2) | 0.0520 (18) | 0.0056 (15) | 0.0149 (14) | 0.0133 (15) |
C4 | 0.0385 (15) | 0.060 (2) | 0.0532 (18) | 0.0126 (14) | 0.0097 (13) | 0.0090 (15) |
C5 | 0.0352 (15) | 0.059 (2) | 0.0554 (19) | 0.0059 (13) | 0.0169 (13) | 0.0055 (15) |
C6 | 0.0348 (14) | 0.0463 (17) | 0.0421 (15) | 0.0018 (12) | 0.0132 (12) | −0.0006 (12) |
C7 | 0.0378 (14) | 0.0491 (18) | 0.0494 (17) | 0.0007 (13) | 0.0195 (13) | −0.0001 (13) |
C8 | 0.0453 (18) | 0.082 (3) | 0.081 (3) | 0.0091 (18) | 0.0328 (18) | 0.022 (2) |
C9 | 0.0447 (15) | 0.0495 (18) | 0.0381 (15) | −0.0038 (13) | 0.0160 (12) | −0.0014 (13) |
C10 | 0.0428 (15) | 0.0471 (17) | 0.0398 (15) | −0.0008 (13) | 0.0151 (12) | −0.0029 (12) |
C11 | 0.076 (3) | 0.076 (3) | 0.065 (2) | 0.006 (2) | 0.029 (2) | 0.028 (2) |
C12 | 0.077 (3) | 0.073 (3) | 0.054 (2) | 0.020 (2) | 0.0181 (18) | 0.0167 (19) |
C13 | 0.059 (2) | 0.063 (2) | 0.0446 (18) | 0.0101 (17) | 0.0224 (15) | 0.0090 (15) |
C14 | 0.0350 (14) | 0.0395 (15) | 0.0379 (14) | 0.0011 (11) | 0.0078 (11) | −0.0063 (11) |
C15 | 0.0398 (15) | 0.0491 (18) | 0.0447 (16) | 0.0014 (13) | 0.0104 (12) | 0.0012 (13) |
C16 | 0.0480 (17) | 0.0517 (19) | 0.0416 (16) | 0.0042 (14) | 0.0076 (13) | 0.0016 (13) |
C17 | 0.0392 (16) | 0.060 (2) | 0.0465 (17) | 0.0129 (14) | 0.0020 (13) | 0.0011 (15) |
C18 | 0.0335 (14) | 0.061 (2) | 0.0468 (17) | 0.0038 (13) | 0.0075 (12) | −0.0026 (15) |
C19 | 0.0327 (13) | 0.0440 (16) | 0.0415 (15) | 0.0018 (11) | 0.0097 (11) | −0.0053 (12) |
C20 | 0.0356 (14) | 0.0473 (17) | 0.0423 (15) | −0.0018 (12) | 0.0135 (12) | −0.0076 (12) |
C21 | 0.0411 (17) | 0.071 (2) | 0.067 (2) | 0.0046 (16) | 0.0235 (16) | 0.0103 (18) |
C22 | 0.0400 (15) | 0.0527 (19) | 0.0398 (15) | −0.0015 (13) | 0.0154 (12) | −0.0026 (13) |
C23 | 0.0383 (14) | 0.0544 (19) | 0.0465 (16) | −0.0005 (13) | 0.0196 (13) | −0.0009 (14) |
C24 | 0.083 (3) | 0.063 (2) | 0.071 (3) | 0.000 (2) | 0.034 (2) | 0.021 (2) |
C25 | 0.072 (3) | 0.090 (3) | 0.064 (2) | 0.025 (2) | 0.024 (2) | 0.028 (2) |
C26 | 0.0430 (17) | 0.092 (3) | 0.053 (2) | 0.0137 (18) | 0.0214 (15) | 0.0254 (19) |
C27 | 0.086 (3) | 0.094 (4) | 0.123 (4) | 0.032 (3) | −0.011 (3) | −0.050 (3) |
C28 | 0.112 (5) | 0.114 (5) | 0.201 (7) | 0.036 (4) | −0.002 (5) | −0.091 (5) |
C29 | 0.116 (5) | 0.126 (5) | 0.125 (5) | −0.024 (4) | 0.045 (4) | −0.082 (4) |
C30 | 0.119 (4) | 0.085 (4) | 0.059 (3) | −0.020 (3) | 0.017 (3) | −0.014 (2) |
C31 | 0.093 (3) | 0.061 (2) | 0.056 (2) | 0.006 (2) | 0.012 (2) | −0.0006 (18) |
C32 | 0.0475 (18) | 0.061 (2) | 0.072 (2) | −0.0005 (16) | 0.0156 (17) | −0.0113 (18) |
C33 | 0.062 (2) | 0.075 (3) | 0.085 (3) | −0.011 (2) | 0.015 (2) | −0.029 (2) |
C34 | 0.094 (3) | 0.083 (3) | 0.091 (3) | −0.026 (3) | 0.041 (3) | −0.045 (3) |
C35 | 0.087 (3) | 0.124 (5) | 0.136 (5) | −0.019 (3) | 0.057 (3) | −0.075 (4) |
C36 | 0.056 (2) | 0.099 (4) | 0.110 (4) | −0.009 (2) | 0.032 (2) | −0.052 (3) |
Geometric parameters (Å, º) top
Zn1—O1 | 2.015 (2) | C10—C13 | 1.414 (4) |
Zn1—O2 | 1.991 (2) | C11—C12 | 1.335 (5) |
Zn1—O3 | 2.047 (2) | C11—H11A | 0.9300 |
Zn1—N1 | 2.065 (2) | C12—C13 | 1.427 (5) |
Zn1—N5 | 2.050 (3) | C12—H12A | 0.9300 |
Zn1—Zn2 | 3.1003 (5) | C13—H13A | 0.9300 |
Zn2—O1 | 2.0366 (19) | C14—C15 | 1.397 (4) |
Zn2—O3 | 2.009 (2) | C14—C19 | 1.422 (4) |
Zn2—O4 | 1.991 (2) | C15—C16 | 1.366 (4) |
Zn2—N3 | 2.070 (2) | C15—H15A | 0.9300 |
Zn2—N6 | 2.065 (3) | C16—C17 | 1.371 (5) |
Cl1—C4 | 1.744 (3) | C16—H16A | 0.9300 |
Cl2—C17 | 1.742 (3) | C17—C18 | 1.358 (5) |
S1—C10 | 1.706 (3) | C18—C19 | 1.408 (4) |
S1—C11 | 1.685 (4) | C18—H18A | 0.9300 |
S2—C23 | 1.691 (3) | C19—C20 | 1.470 (4) |
S2—C24 | 1.687 (4) | C20—C21 | 1.498 (4) |
O1—C1 | 1.335 (3) | C21—H21A | 0.9600 |
O2—C9 | 1.282 (4) | C21—H21B | 0.9600 |
O3—C14 | 1.333 (3) | C21—H21C | 0.9600 |
O4—C22 | 1.282 (3) | C22—C23 | 1.466 (4) |
N1—C7 | 1.294 (4) | C23—C26 | 1.406 (4) |
N1—N2 | 1.389 (3) | C24—C25 | 1.323 (6) |
N2—C9 | 1.303 (4) | C24—H24A | 0.9300 |
N3—C20 | 1.291 (4) | C25—C26 | 1.445 (5) |
N3—N4 | 1.392 (3) | C25—H25A | 0.9300 |
N4—C22 | 1.310 (4) | C26—H26A | 0.9300 |
N5—C31 | 1.317 (4) | C27—C28 | 1.376 (7) |
N5—C27 | 1.332 (6) | C27—H27A | 0.9300 |
N6—C32 | 1.314 (4) | C28—C29 | 1.374 (8) |
N6—C36 | 1.330 (5) | C28—H28A | 0.9300 |
C1—C2 | 1.397 (4) | C29—C30 | 1.349 (8) |
C1—C6 | 1.415 (4) | C29—H29A | 0.9300 |
C2—C3 | 1.369 (4) | C30—C31 | 1.367 (6) |
C2—H2B | 0.9300 | C30—H30A | 0.9300 |
C3—C4 | 1.381 (5) | C31—H31A | 0.9300 |
C3—H3A | 0.9300 | C32—C33 | 1.359 (5) |
C4—C5 | 1.357 (5) | C32—H32A | 0.9300 |
C5—C6 | 1.404 (4) | C33—C34 | 1.324 (6) |
C5—H5A | 0.9300 | C33—H33A | 0.9300 |
C6—C7 | 1.468 (4) | C34—C35 | 1.381 (7) |
C7—C8 | 1.500 (4) | C34—H34A | 0.9300 |
C8—H8A | 0.9600 | C35—C36 | 1.362 (6) |
C8—H8B | 0.9600 | C35—H35A | 0.9300 |
C8—H8C | 0.9600 | C36—H36A | 0.9300 |
C9—C10 | 1.465 (4) | ||
O2—Zn1—O1 | 152.81 (11) | C13—C10—C9 | 126.8 (3) |
O2—Zn1—O3 | 102.69 (9) | C13—C10—S1 | 111.9 (2) |
O1—Zn1—O3 | 80.02 (8) | C9—C10—S1 | 121.3 (2) |
O2—Zn1—N5 | 104.05 (12) | C12—C11—S1 | 112.8 (3) |
O1—Zn1—N5 | 102.33 (11) | C12—C11—H11A | 123.6 |
O3—Zn1—N5 | 97.79 (10) | S1—C11—H11A | 123.6 |
O2—Zn1—N1 | 78.71 (10) | C11—C12—C13 | 114.4 (3) |
O1—Zn1—N1 | 86.45 (9) | C11—C12—H12A | 122.8 |
O3—Zn1—N1 | 151.68 (10) | C13—C12—H12A | 122.8 |
N5—Zn1—N1 | 109.41 (11) | C10—C13—C12 | 108.9 (3) |
O2—Zn1—Zn2 | 135.74 (7) | C10—C13—H13A | 125.6 |
O1—Zn1—Zn2 | 40.33 (5) | C12—C13—H13A | 125.6 |
O3—Zn1—Zn2 | 39.70 (6) | O3—C14—C15 | 118.3 (3) |
N5—Zn1—Zn2 | 103.77 (8) | O3—C14—C19 | 123.4 (3) |
N1—Zn1—Zn2 | 122.26 (8) | C15—C14—C19 | 118.3 (3) |
O4—Zn2—O3 | 149.11 (11) | C16—C15—C14 | 123.1 (3) |
O4—Zn2—O1 | 102.24 (8) | C16—C15—H15A | 118.5 |
O3—Zn2—O1 | 80.41 (8) | C14—C15—H15A | 118.5 |
O4—Zn2—N6 | 108.25 (12) | C15—C16—C17 | 118.4 (3) |
O3—Zn2—N6 | 101.48 (10) | C15—C16—H16A | 120.8 |
O1—Zn2—N6 | 99.64 (10) | C17—C16—H16A | 120.8 |
O4—Zn2—N3 | 78.08 (9) | C18—C17—C16 | 121.0 (3) |
O3—Zn2—N3 | 87.10 (9) | C18—C17—Cl2 | 119.2 (3) |
O1—Zn2—N3 | 155.34 (10) | C16—C17—Cl2 | 119.8 (3) |
N6—Zn2—N3 | 103.65 (10) | C17—C18—C19 | 122.3 (3) |
O4—Zn2—Zn1 | 134.64 (7) | C17—C18—H18A | 118.8 |
O3—Zn2—Zn1 | 40.60 (5) | C19—C18—H18A | 118.8 |
O1—Zn2—Zn1 | 39.81 (6) | C18—C19—C14 | 116.9 (3) |
N6—Zn2—Zn1 | 103.25 (8) | C18—C19—C20 | 117.1 (3) |
N3—Zn2—Zn1 | 124.81 (7) | C14—C19—C20 | 126.0 (3) |
C11—S1—C10 | 91.97 (18) | N3—C20—C19 | 120.5 (3) |
C24—S2—C23 | 92.33 (18) | N3—C20—C21 | 120.0 (3) |
C1—O1—Zn1 | 128.80 (18) | C19—C20—C21 | 119.5 (3) |
C1—O1—Zn2 | 131.03 (19) | C20—C21—H21A | 109.5 |
Zn1—O1—Zn2 | 99.85 (8) | C20—C21—H21B | 109.5 |
C9—O2—Zn1 | 110.29 (19) | H21A—C21—H21B | 109.5 |
C14—O3—Zn2 | 128.56 (18) | C20—C21—H21C | 109.5 |
C14—O3—Zn1 | 131.74 (19) | H21A—C21—H21C | 109.5 |
Zn2—O3—Zn1 | 99.70 (8) | H21B—C21—H21C | 109.5 |
C22—O4—Zn2 | 110.26 (19) | O4—C22—N4 | 126.5 (3) |
C7—N1—N2 | 116.4 (2) | O4—C22—C23 | 116.5 (3) |
C7—N1—Zn1 | 131.7 (2) | N4—C22—C23 | 117.0 (3) |
N2—N1—Zn1 | 111.80 (19) | C26—C23—C22 | 125.2 (3) |
C9—N2—N1 | 110.5 (2) | C26—C23—S2 | 112.4 (2) |
C20—N3—N4 | 117.0 (2) | C22—C23—S2 | 122.4 (2) |
C20—N3—Zn2 | 131.3 (2) | C25—C24—S2 | 112.4 (3) |
N4—N3—Zn2 | 111.70 (18) | C25—C24—H24A | 123.8 |
C22—N4—N3 | 109.8 (2) | S2—C24—H24A | 123.8 |
C31—N5—C27 | 118.0 (4) | C24—C25—C26 | 114.5 (3) |
C31—N5—Zn1 | 120.4 (3) | C24—C25—H25A | 122.7 |
C27—N5—Zn1 | 121.6 (3) | C26—C25—H25A | 122.7 |
C32—N6—C36 | 115.8 (3) | C23—C26—C25 | 108.1 (3) |
C32—N6—Zn2 | 119.9 (2) | C23—C26—H26A | 125.9 |
C36—N6—Zn2 | 123.7 (3) | C25—C26—H26A | 125.9 |
O1—C1—C2 | 118.0 (3) | N5—C27—C28 | 121.6 (5) |
O1—C1—C6 | 123.5 (3) | N5—C27—H27A | 119.2 |
C2—C1—C6 | 118.5 (3) | C28—C27—H27A | 119.2 |
C3—C2—C1 | 122.8 (3) | C29—C28—C27 | 118.7 (6) |
C3—C2—H2B | 118.6 | C29—C28—H28A | 120.6 |
C1—C2—H2B | 118.6 | C27—C28—H28A | 120.6 |
C2—C3—C4 | 118.3 (3) | C30—C29—C28 | 119.6 (5) |
C2—C3—H3A | 120.8 | C30—C29—H29A | 120.2 |
C4—C3—H3A | 120.8 | C28—C29—H29A | 120.2 |
C5—C4—C3 | 120.7 (3) | C29—C30—C31 | 118.1 (5) |
C5—C4—Cl1 | 119.8 (3) | C29—C30—H30A | 120.9 |
C3—C4—Cl1 | 119.5 (3) | C31—C30—H30A | 120.9 |
C4—C5—C6 | 122.5 (3) | N5—C31—C30 | 123.8 (4) |
C4—C5—H5A | 118.8 | N5—C31—H31A | 118.1 |
C6—C5—H5A | 118.8 | C30—C31—H31A | 118.1 |
C5—C6—C1 | 117.2 (3) | N6—C32—C33 | 124.1 (4) |
C5—C6—C7 | 117.0 (3) | N6—C32—H32A | 118.0 |
C1—C6—C7 | 125.8 (3) | C33—C32—H32A | 118.0 |
N1—C7—C6 | 120.4 (3) | C34—C33—C32 | 119.9 (4) |
N1—C7—C8 | 120.0 (3) | C34—C33—H33A | 120.0 |
C6—C7—C8 | 119.6 (3) | C32—C33—H33A | 120.0 |
C7—C8—H8A | 109.5 | C33—C34—C35 | 118.1 (4) |
C7—C8—H8B | 109.5 | C33—C34—H34A | 120.9 |
H8A—C8—H8B | 109.5 | C35—C34—H34A | 120.9 |
C7—C8—H8C | 109.5 | C36—C35—C34 | 118.4 (4) |
H8A—C8—H8C | 109.5 | C36—C35—H35A | 120.8 |
H8B—C8—H8C | 109.5 | C34—C35—H35A | 120.8 |
O2—C9—N2 | 126.9 (3) | N6—C36—C35 | 123.5 (4) |
O2—C9—C10 | 116.3 (3) | N6—C36—H36A | 118.2 |
N2—C9—C10 | 116.8 (3) | C35—C36—H36A | 118.2 |
O2—Zn1—Zn2—O4 | 176.48 (14) | O1—Zn2—N6—C32 | 163.2 (3) |
O1—Zn1—Zn2—O4 | −44.00 (15) | N3—Zn2—N6—C32 | −8.7 (3) |
O3—Zn1—Zn2—O4 | 134.52 (15) | Zn1—Zn2—N6—C32 | 122.7 (3) |
N5—Zn1—Zn2—O4 | 48.92 (14) | O4—Zn2—N6—C36 | 98.7 (4) |
N1—Zn1—Zn2—O4 | −75.09 (14) | O3—Zn2—N6—C36 | −89.8 (4) |
O2—Zn1—Zn2—O3 | 41.96 (15) | O1—Zn2—N6—C36 | −7.7 (4) |
O1—Zn1—Zn2—O3 | −178.53 (13) | N3—Zn2—N6—C36 | −179.6 (4) |
N5—Zn1—Zn2—O3 | −85.60 (13) | Zn1—Zn2—N6—C36 | −48.2 (4) |
N1—Zn1—Zn2—O3 | 150.39 (13) | Zn1—O1—C1—C2 | −163.8 (2) |
O2—Zn1—Zn2—O1 | −139.52 (15) | Zn2—O1—C1—C2 | 24.1 (4) |
O3—Zn1—Zn2—O1 | 178.53 (13) | Zn1—O1—C1—C6 | 17.0 (4) |
N5—Zn1—Zn2—O1 | 92.93 (13) | Zn2—O1—C1—C6 | −155.2 (2) |
N1—Zn1—Zn2—O1 | −31.09 (13) | O1—C1—C2—C3 | −178.9 (3) |
O2—Zn1—Zn2—N6 | −50.30 (14) | C6—C1—C2—C3 | 0.3 (5) |
O1—Zn1—Zn2—N6 | 89.21 (12) | C1—C2—C3—C4 | 0.3 (6) |
O3—Zn1—Zn2—N6 | −92.26 (12) | C2—C3—C4—C5 | −0.8 (6) |
N5—Zn1—Zn2—N6 | −177.86 (10) | C2—C3—C4—Cl1 | 177.7 (3) |
N1—Zn1—Zn2—N6 | 58.13 (12) | C3—C4—C5—C6 | 0.7 (6) |
O2—Zn1—Zn2—N3 | 67.02 (14) | Cl1—C4—C5—C6 | −177.8 (3) |
O1—Zn1—Zn2—N3 | −153.46 (13) | C4—C5—C6—C1 | 0.0 (5) |
O3—Zn1—Zn2—N3 | 25.07 (13) | C4—C5—C6—C7 | 179.1 (3) |
N5—Zn1—Zn2—N3 | −60.53 (12) | O1—C1—C6—C5 | 178.7 (3) |
N1—Zn1—Zn2—N3 | 175.45 (11) | C2—C1—C6—C5 | −0.5 (4) |
O2—Zn1—O1—C1 | −76.6 (3) | O1—C1—C6—C7 | −0.3 (5) |
O3—Zn1—O1—C1 | −175.0 (3) | C2—C1—C6—C7 | −179.5 (3) |
N5—Zn1—O1—C1 | 89.2 (2) | N2—N1—C7—C6 | 177.7 (3) |
N1—Zn1—O1—C1 | −19.9 (2) | Zn1—N1—C7—C6 | −6.3 (5) |
Zn2—Zn1—O1—C1 | −174.0 (3) | N2—N1—C7—C8 | −2.5 (5) |
O2—Zn1—O1—Zn2 | 97.41 (18) | Zn1—N1—C7—C8 | 173.5 (3) |
O3—Zn1—O1—Zn2 | −0.96 (8) | C5—C6—C7—N1 | 175.9 (3) |
N5—Zn1—O1—Zn2 | −96.84 (11) | C1—C6—C7—N1 | −5.1 (5) |
N1—Zn1—O1—Zn2 | 154.06 (11) | C5—C6—C7—C8 | −3.9 (5) |
O4—Zn2—O1—C1 | −36.6 (3) | C1—C6—C7—C8 | 175.1 (3) |
O3—Zn2—O1—C1 | 174.8 (3) | Zn1—O2—C9—N2 | −10.1 (4) |
N6—Zn2—O1—C1 | 74.6 (3) | Zn1—O2—C9—C10 | 170.4 (2) |
N3—Zn2—O1—C1 | −124.6 (3) | N1—N2—C9—O2 | −0.1 (5) |
Zn1—Zn2—O1—C1 | 173.8 (3) | N1—N2—C9—C10 | 179.5 (3) |
O4—Zn2—O1—Zn1 | 149.61 (11) | O2—C9—C10—C13 | 7.0 (5) |
O3—Zn2—O1—Zn1 | 0.97 (8) | N2—C9—C10—C13 | −172.6 (3) |
N6—Zn2—O1—Zn1 | −99.17 (11) | O2—C9—C10—S1 | −173.2 (2) |
N3—Zn2—O1—Zn1 | 61.6 (2) | N2—C9—C10—S1 | 7.2 (4) |
O1—Zn1—O2—C9 | 69.3 (3) | C11—S1—C10—C13 | −1.6 (3) |
O3—Zn1—O2—C9 | 162.1 (2) | C11—S1—C10—C9 | 178.6 (3) |
N5—Zn1—O2—C9 | −96.4 (2) | C10—S1—C11—C12 | 0.5 (4) |
N1—Zn1—O2—C9 | 11.1 (2) | S1—C11—C12—C13 | 0.7 (5) |
Zn2—Zn1—O2—C9 | 136.16 (19) | C9—C10—C13—C12 | −178.0 (3) |
O4—Zn2—O3—C14 | 80.5 (3) | S1—C10—C13—C12 | 2.2 (4) |
O1—Zn2—O3—C14 | 178.3 (3) | C11—C12—C13—C10 | −1.8 (5) |
N6—Zn2—O3—C14 | −83.7 (2) | Zn2—O3—C14—C15 | 163.1 (2) |
N3—Zn2—O3—C14 | 19.7 (2) | Zn1—O3—C14—C15 | −17.8 (4) |
Zn1—Zn2—O3—C14 | 179.3 (3) | Zn2—O3—C14—C19 | −16.9 (4) |
O4—Zn2—O3—Zn1 | −98.79 (16) | Zn1—O3—C14—C19 | 162.2 (2) |
O1—Zn2—O3—Zn1 | −0.96 (8) | O3—C14—C15—C16 | 179.4 (3) |
N6—Zn2—O3—Zn1 | 97.03 (10) | C19—C14—C15—C16 | −0.6 (5) |
N3—Zn2—O3—Zn1 | −159.62 (10) | C14—C15—C16—C17 | −0.2 (5) |
O2—Zn1—O3—C14 | 29.3 (3) | C15—C16—C17—C18 | 1.1 (5) |
O1—Zn1—O3—C14 | −178.3 (3) | C15—C16—C17—Cl2 | −177.3 (3) |
N5—Zn1—O3—C14 | −77.0 (3) | C16—C17—C18—C19 | −1.2 (5) |
N1—Zn1—O3—C14 | 119.0 (3) | Cl2—C17—C18—C19 | 177.2 (3) |
Zn2—Zn1—O3—C14 | −179.2 (3) | C17—C18—C19—C14 | 0.3 (5) |
O2—Zn1—O3—Zn2 | −151.43 (11) | C17—C18—C19—C20 | −178.7 (3) |
O1—Zn1—O3—Zn2 | 0.97 (8) | O3—C14—C19—C18 | −179.4 (3) |
N5—Zn1—O3—Zn2 | 102.20 (11) | C15—C14—C19—C18 | 0.6 (4) |
N1—Zn1—O3—Zn2 | −61.7 (2) | O3—C14—C19—C20 | −0.5 (5) |
O3—Zn2—O4—C22 | −78.6 (3) | C15—C14—C19—C20 | 179.5 (3) |
O1—Zn2—O4—C22 | −170.4 (2) | N4—N3—C20—C19 | −179.1 (3) |
N6—Zn2—O4—C22 | 85.0 (2) | Zn2—N3—C20—C19 | 3.6 (4) |
N3—Zn2—O4—C22 | −15.6 (2) | N4—N3—C20—C21 | 0.9 (4) |
Zn1—Zn2—O4—C22 | −143.28 (19) | Zn2—N3—C20—C21 | −176.4 (2) |
O2—Zn1—N1—C7 | 172.2 (3) | C18—C19—C20—N3 | −173.9 (3) |
O1—Zn1—N1—C7 | 15.1 (3) | C14—C19—C20—N3 | 7.2 (5) |
O3—Zn1—N1—C7 | 76.4 (4) | C18—C19—C20—C21 | 6.1 (4) |
N5—Zn1—N1—C7 | −86.7 (3) | C14—C19—C20—C21 | −172.8 (3) |
Zn2—Zn1—N1—C7 | 34.7 (3) | Zn2—O4—C22—N4 | 14.2 (4) |
O2—Zn1—N1—N2 | −11.7 (2) | Zn2—O4—C22—C23 | −165.3 (2) |
O1—Zn1—N1—N2 | −168.8 (2) | N3—N4—C22—O4 | 0.1 (5) |
O3—Zn1—N1—N2 | −107.5 (3) | N3—N4—C22—C23 | 179.6 (3) |
N5—Zn1—N1—N2 | 89.4 (2) | O4—C22—C23—C26 | −13.1 (5) |
Zn2—Zn1—N1—N2 | −149.20 (17) | N4—C22—C23—C26 | 167.3 (3) |
C7—N1—N2—C9 | −173.3 (3) | O4—C22—C23—S2 | 167.5 (3) |
Zn1—N1—N2—C9 | 9.9 (3) | N4—C22—C23—S2 | −12.1 (4) |
O4—Zn2—N3—C20 | −166.1 (3) | C24—S2—C23—C26 | 3.5 (3) |
O3—Zn2—N3—C20 | −13.4 (3) | C24—S2—C23—C22 | −177.0 (3) |
O1—Zn2—N3—C20 | −72.7 (4) | C23—S2—C24—C25 | −1.4 (4) |
N6—Zn2—N3—C20 | 87.7 (3) | S2—C24—C25—C26 | −1.1 (6) |
Zn1—Zn2—N3—C20 | −29.4 (3) | C22—C23—C26—C25 | 176.0 (3) |
O4—Zn2—N3—N4 | 16.43 (19) | S2—C23—C26—C25 | −4.5 (4) |
O3—Zn2—N3—N4 | 169.2 (2) | C24—C25—C26—C23 | 3.5 (6) |
O1—Zn2—N3—N4 | 109.8 (3) | C31—N5—C27—C28 | 4.5 (9) |
N6—Zn2—N3—N4 | −89.7 (2) | Zn1—N5—C27—C28 | −177.9 (6) |
Zn1—Zn2—N3—N4 | 153.14 (16) | N5—C27—C28—C29 | −1.1 (12) |
C20—N3—N4—C22 | 168.2 (3) | C27—C28—C29—C30 | −2.7 (12) |
Zn2—N3—N4—C22 | −13.9 (3) | C28—C29—C30—C31 | 2.9 (10) |
O2—Zn1—N5—C31 | 135.2 (3) | C27—N5—C31—C30 | −4.3 (7) |
O1—Zn1—N5—C31 | −38.2 (3) | Zn1—N5—C31—C30 | 178.1 (4) |
O3—Zn1—N5—C31 | −119.6 (3) | C29—C30—C31—N5 | 0.6 (8) |
N1—Zn1—N5—C31 | 52.4 (3) | C36—N6—C32—C33 | −1.6 (6) |
Zn2—Zn1—N5—C31 | −79.6 (3) | Zn2—N6—C32—C33 | −173.2 (4) |
O2—Zn1—N5—C27 | −42.4 (4) | N6—C32—C33—C34 | −1.3 (8) |
O1—Zn1—N5—C27 | 144.3 (4) | C32—C33—C34—C35 | 3.3 (9) |
O3—Zn1—N5—C27 | 62.9 (4) | C33—C34—C35—C36 | −2.6 (9) |
N1—Zn1—N5—C27 | −125.2 (4) | C32—N6—C36—C35 | 2.3 (8) |
Zn2—Zn1—N5—C27 | 102.9 (4) | Zn2—N6—C36—C35 | 173.6 (5) |
O4—Zn2—N6—C32 | −90.4 (3) | C34—C35—C36—N6 | −0.3 (10) |
O3—Zn2—N6—C32 | 81.1 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2B···O4 | 0.93 | 2.21 | 3.065 (3) | 153 |
C2—H2B···O4 | 0.93 | 2.21 | 3.066 (4) | 153 |
C8—H8A···N2 | 0.96 | 2.19 | 2.663 (5) | 109 |
C15—H15A···O2 | 0.93 | 2.19 | 3.049 (4) | 154 |
C21—H21A···N4 | 0.96 | 2.19 | 2.673 (5) | 110 |
C26—H26A···Cl2i | 0.93 | 2.71 | 3.501 (4) | 143 |
Symmetry code: (i) x−1/2, −y+3/2, z−1/2. |