Bis{μ-2′-[1-(4-chloro-2-oxido­phenyl)­ethyl­idene]­thio­phene-2-carbohydrazidato}bis­[pyridine­zinc(II)]

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 Zn...Zn separation is 3.1003 (5) Å and the geometry of both Zn atoms is square pyramidal.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.048
• wR factor = 0.138
• Data-to-parameter ratio = 17.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.02 Ratio
PLAT241_ALERT_2_B Check High   U(eq) as Compared to Neighbors ....        C28

Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.38
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.39 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C12    -   C13      =       5.66 su
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....         O2
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....         O4
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        C35
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         N5

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

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)]

Crystal data

[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) Å^3	Block, yellow
Z = 4	0.44 × 0.39 × 0.37 mm

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.138	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0743P)^2 + 2.3755P] where P = (Fo^2 + 2Fc^2)/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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···Cl2^i	0.93	2.71	3.501 (4)	143

Symmetry code: (i) x−1/2, −y+3/2, z−1/2.