Di­chloro{2,2'-thio­bis­[(4S)-4-iso­propyl-1,3-oxazolinyl­phenyl]}zinc(II)

The title compound, [ZnCl₂(C₂₄H₂₈N₂O₂S)], consists of a tetrahedral Zn atom coordinated by a C₂-symmetric bis-oxazoline ligand. In order to participate in complexation, the ligand becomes bowl-shaped, which results in a distance between the Zn and S atoms of 5.2237 (8) Å.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.028
• wR factor = 0.063
• Data-to-parameter ratio = 19.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



ABSTM_02  Alert C The ratio of Tmax/Tmin expected RT(exp) is > 1.10
          Absorption corrections should be applied.
          Tmin and Tmax expected:      0.526     0.605
          RT(exp) =      1.150

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.48
         From the CIF: _reflns_number_total               5650
         Count of symmetry unique reflns         3191
         Completeness (_total/calc)            177.06%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured      2459
         Fraction of Friedel pairs measured     0.771
         Are heavy atom types Z>Si present          yes
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

Computing details

Data collection: locally modified CAD-4 Software (Enraf-Nonius, 1989); cell refinement: SET4 (de Boer & Duisenberg, 1984); data reduction: HELENA (Spek, 1997); program(s) used to solve structure: DIRDIF (Beurskens et al., 1992); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993); molecular graphics: PLATON (Spek, 2001); software used to prepare material for publication: PLATON.

Dichloro{2,2'-thiobis[(4S)-4-isopropyl-1,3-oxazolinylphenyl]}zinc(II)

Crystal data

[ZnCl2(C24H28N2O2S)]	Least Squares Treatment of 25 SET4 setting angles (de Boer & Duisenberg).
Mr = 544.84	Dx = 1.469 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 9.5848 (6) Å	θ = 11.5–14.1°
b = 15.6021 (9) Å	µ = 1.32 mm^−1
c = 16.4734 (9) Å	T = 150 K
V = 2463.5 (2) Å^3	Irregular, colourless
Z = 4	0.50 × 0.45 × 0.38 mm
F(000) = 1128

Data collection

Enraf-Nonius CAD-4 Turbo diffractometer	Rint = 0.019
Radiation source: Rotating Anode	θmax = 27.5°, θmin = 1.8°
Graphite monochromator	h = 0→12
ω/2θ scans	k = −20→20
6371 measured reflections	l = 0→21
5650 independent reflections	3 standard reflections every 60 min
5246 reflections with I > 2σ(I)	intensity decay: 8%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.028	H-atom parameters constrained
wR(F^2) = 0.063	w = 1/[σ^2(Fo^2) + (0.0352P)^2 + 0.52P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.003
5650 reflections	Δρmax = 0.27 e Å^−3
293 parameters	Δρmin = −0.21 e Å^−3
0 restraints	Absolute structure: Flack (1983), 2463 Friedel pairs
Primary atom site location: real-space vector search	Absolute structure parameter: −0.007 (8)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F^{2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F}2, conventional R-factors R are based on F, with F set to zero for negative F^{2. The observed criterion of F}2 > σ(F^{2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F}2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Zn1	0.77880 (3)	0.86420 (2)	0.79752 (1)	0.0199 (1)
Cl1	1.00628 (6)	0.85130 (4)	0.82281 (3)	0.0327 (2)
Cl2	0.66565 (8)	0.96469 (4)	0.86548 (4)	0.0393 (2)
S1	0.56357 (8)	0.66075 (4)	0.57902 (4)	0.0354 (2)
O1	0.7194 (2)	0.85271 (9)	0.54453 (8)	0.0252 (4)
O2	0.5807 (2)	0.62536 (10)	0.77661 (9)	0.0278 (5)
N1	0.7486 (2)	0.88146 (10)	0.67630 (10)	0.0179 (5)
N2	0.6949 (2)	0.74510 (11)	0.81063 (10)	0.0183 (5)
C1	0.7410 (3)	0.66496 (14)	0.61029 (12)	0.0271 (7)
C2	0.8081 (3)	0.5858 (2)	0.61570 (15)	0.0393 (9)
C3	0.9485 (4)	0.5813 (2)	0.6325 (2)	0.0456 (9)
C4	1.0241 (3)	0.6547 (2)	0.6485 (2)	0.0412 (10)
C5	0.9574 (3)	0.7337 (2)	0.64582 (15)	0.0295 (8)
C6	0.8168 (2)	0.73977 (14)	0.62545 (13)	0.0225 (6)
C7	0.7577 (2)	0.82757 (13)	0.61867 (12)	0.0195 (6)
C8	0.6655 (3)	0.94047 (14)	0.55419 (14)	0.0262 (7)
C9	0.7048 (2)	0.96502 (13)	0.64139 (12)	0.0196 (6)
C10	0.8240 (2)	1.02938 (14)	0.65066 (14)	0.0255 (6)
C11	0.9564 (3)	1.0000 (2)	0.6083 (2)	0.0409 (9)
C12	0.7795 (3)	1.11808 (14)	0.6214 (2)	0.0393 (9)
C13	0.4766 (2)	0.7407 (2)	0.63537 (14)	0.0269 (7)
C14	0.3774 (3)	0.7886 (2)	0.5934 (2)	0.0363 (9)
C15	0.2997 (3)	0.8504 (2)	0.6319 (2)	0.0392 (9)
C16	0.3215 (2)	0.8679 (2)	0.7134 (2)	0.0348 (7)
C17	0.4213 (2)	0.8221 (2)	0.75593 (14)	0.0269 (7)
C18	0.4962 (2)	0.75711 (14)	0.71850 (12)	0.0213 (6)
C19	0.5970 (2)	0.71028 (14)	0.76943 (12)	0.0205 (6)
C20	0.6967 (3)	0.59594 (15)	0.82665 (14)	0.0315 (8)
C21	0.7572 (2)	0.67810 (12)	0.86360 (12)	0.0204 (6)
C22	0.7188 (3)	0.69590 (14)	0.95218 (12)	0.0258 (6)
C23	0.5627 (3)	0.6960 (2)	0.9657 (2)	0.0473 (9)
C24	0.7896 (3)	0.6318 (2)	1.00888 (13)	0.0332 (7)
H2	0.7564	0.5345	0.60771	0.0470*
H3	0.9939	0.5271	0.6331	0.0550*
H4	1.1206	0.6512	0.6611	0.0500*
H5	1.0085	0.7843	0.65807	0.0350*
H8A	0.5630	0.94198	0.54656	0.0310*
H8B	0.7095	0.97985	0.51464	0.0310*
H9	0.6203	0.98652	0.67065	0.0240*
H10	0.8454	1.03409	0.70991	0.0310*
H11A	1.0306	1.0421	0.6175	0.0610*
H11B	0.9389	0.9946	0.5500	0.0610*
H11C	0.9851	0.9443	0.6302	0.0610*
H12A	0.6944	1.1356	0.6500	0.0590*
H12B	0.761	1.1162	0.5629	0.0590*
H12C	0.8540	1.1594	0.6326	0.0590*
H14	0.3632	0.7783	0.5371	0.0440*
H15	0.2307	0.8813	0.6026	0.0470*
H16	0.2685	0.9111	0.7398	0.0420*
H17	0.4386	0.8353	0.81132	0.0320*
H20A	0.7675	0.56603	0.79325	0.0380*
H20B	0.6637	0.55653	0.86965	0.0380*
H21	0.8609	0.67825	0.85733	0.0240*
H22	0.7545	0.75428	0.96619	0.0310*
H23A	0.5185	0.7355	0.9272	0.0710*
H23B	0.5425	0.7145	1.0213	0.0710*
H23C	0.5260	0.6381	0.9573	0.0710*
H24A	0.7671	0.6460	1.06531	0.0500*
H24B	0.8909	0.6343	1.0011	0.0500*
H24C	0.7563	0.5738	0.9966	0.0500*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0290 (1)	0.0161 (1)	0.0146 (1)	−0.0025 (1)	−0.0027 (1)	0.0005 (1)
Cl1	0.0296 (3)	0.0380 (3)	0.0304 (3)	−0.0050 (3)	−0.0093 (2)	0.0055 (2)
Cl2	0.0568 (4)	0.0316 (3)	0.0296 (3)	0.0091 (3)	0.0002 (3)	−0.0124 (2)
S1	0.0496 (4)	0.0348 (3)	0.0217 (3)	−0.0166 (3)	−0.0001 (3)	−0.0108 (2)
O1	0.0368 (8)	0.0233 (8)	0.0155 (6)	−0.0007 (8)	−0.0030 (7)	0.0010 (6)
O2	0.0400 (9)	0.0192 (8)	0.0241 (8)	−0.0065 (7)	−0.0045 (7)	0.0004 (6)
N1	0.0208 (9)	0.0156 (8)	0.0172 (7)	−0.0032 (6)	−0.0003 (6)	0.0022 (6)
N2	0.0239 (9)	0.0181 (8)	0.0130 (8)	−0.0015 (7)	0.0009 (7)	0.0027 (6)
C1	0.0446 (15)	0.0220 (10)	0.0146 (9)	−0.0025 (10)	0.0077 (9)	−0.0028 (8)
C2	0.070 (2)	0.0227 (12)	0.0251 (12)	−0.0010 (13)	0.0108 (13)	−0.0048 (9)
C3	0.075 (2)	0.0293 (14)	0.0324 (14)	0.0226 (14)	0.0138 (15)	0.0036 (11)
C4	0.047 (2)	0.043 (2)	0.0335 (13)	0.0186 (13)	0.0066 (12)	0.0061 (12)
C5	0.0339 (14)	0.0301 (13)	0.0245 (12)	0.0038 (10)	0.0052 (10)	0.0028 (10)
C6	0.0326 (13)	0.0203 (10)	0.0145 (9)	0.0006 (9)	0.0055 (9)	0.0004 (8)
C7	0.0203 (11)	0.0219 (10)	0.0162 (9)	−0.0038 (8)	0.0010 (8)	0.0023 (8)
C8	0.0330 (13)	0.0240 (11)	0.0217 (10)	0.0004 (10)	−0.0048 (10)	0.0044 (9)
C9	0.0210 (11)	0.0188 (9)	0.0190 (9)	−0.0007 (9)	−0.0016 (9)	0.0025 (8)
C10	0.0303 (12)	0.0183 (10)	0.0280 (11)	−0.0056 (9)	−0.0025 (9)	0.0043 (9)
C11	0.0250 (13)	0.0317 (13)	0.066 (2)	−0.0069 (11)	0.0028 (13)	0.0084 (13)
C12	0.0415 (14)	0.0194 (12)	0.057 (2)	−0.0029 (11)	−0.0035 (14)	0.0091 (10)
C13	0.0313 (13)	0.0298 (12)	0.0197 (11)	−0.0147 (10)	−0.0024 (9)	0.0005 (9)
C14	0.0358 (14)	0.046 (2)	0.0271 (13)	−0.0138 (12)	−0.0136 (11)	0.0064 (11)
C15	0.0229 (12)	0.049 (2)	0.0457 (14)	−0.0065 (12)	−0.0092 (11)	0.0176 (13)
C16	0.0263 (11)	0.0378 (13)	0.0402 (13)	0.0033 (11)	0.0053 (10)	0.0087 (12)
C17	0.0276 (12)	0.0309 (12)	0.0221 (11)	−0.0034 (10)	0.0037 (9)	0.0032 (9)
C18	0.0216 (10)	0.0248 (10)	0.0174 (10)	−0.0072 (9)	−0.0008 (8)	0.0038 (8)
C19	0.0274 (11)	0.0218 (10)	0.0122 (9)	−0.0022 (9)	0.0062 (8)	0.0004 (8)
C20	0.048 (2)	0.0196 (10)	0.0269 (11)	0.0000 (11)	−0.0031 (11)	0.0018 (9)
C21	0.0259 (12)	0.0177 (9)	0.0176 (9)	0.0007 (8)	0.0025 (8)	0.0024 (7)
C22	0.0330 (12)	0.0278 (11)	0.0165 (9)	0.0058 (11)	−0.0007 (10)	0.0021 (8)
C23	0.0333 (14)	0.085 (2)	0.0236 (13)	0.015 (2)	0.0068 (11)	0.0126 (14)
C24	0.0390 (13)	0.0385 (13)	0.0221 (10)	0.0055 (13)	−0.0009 (10)	0.0080 (10)

Geometric parameters (Å, º)

Zn1—S1	5.2237 (8)	C20—C21	1.533 (3)
Zn1—Cl1	2.2289 (7)	C21—C22	1.530 (3)
Zn1—Cl2	2.2107 (7)	C22—C23	1.513 (4)
Zn1—N1	2.0357 (17)	C22—C24	1.527 (4)
Zn1—N2	2.0363 (18)	C2—H2	0.9505
S1—C1	1.778 (3)	C3—H3	0.9511
S1—C13	1.764 (3)	C4—H4	0.9495
O1—C7	1.334 (2)	C5—H5	0.9507
O1—C8	1.472 (3)	C8—H8A	0.9907
O2—C19	1.339 (3)	C8—H8B	0.9899
O2—C20	1.458 (3)	C9—H9	1.0004
N1—C7	1.271 (3)	C10—H10	1.0001
N1—C9	1.485 (3)	C11—H11A	0.9799
N2—C19	1.279 (3)	C11—H11B	0.9786
N2—C21	1.487 (3)	C11—H11C	0.9803
C1—C2	1.395 (4)	C12—H12A	0.9808
C1—C6	1.397 (3)	C12—H12B	0.9803
C2—C3	1.376 (5)	C12—H12C	0.9796
C3—C4	1.381 (5)	C14—H14	0.9511
C4—C5	1.389 (4)	C15—H15	0.9501
C5—C6	1.392 (3)	C16—H16	0.9495
C6—C7	1.487 (3)	C17—H17	0.9500
C8—C9	1.534 (3)	C20—H20A	0.9905
C9—C10	1.529 (3)	C20—H20B	0.9899
C10—C11	1.519 (4)	C21—H21	0.9993
C10—C12	1.526 (3)	C22—H22	1.0000
C13—C14	1.393 (4)	C23—H23A	0.9806
C13—C18	1.406 (3)	C23—H23B	0.9796
C14—C15	1.374 (4)	C23—H23C	0.9793
C15—C16	1.386 (5)	C24—H24A	0.9797
C16—C17	1.384 (4)	C24—H24B	0.9801
C17—C18	1.387 (3)	C24—H24C	0.9807
C18—C19	1.473 (3)
Zn1···C5	3.650 (3)	C24···H20B	2.8453
Zn1···C11	4.136 (3)	C24···H2^x	3.0947
Zn1···C17	3.556 (2)	C24···H11A^ix	3.0435
Zn1···H5	3.4174	H2···C24^xi	3.0947
Zn1···H10	3.0848	H2···H24C^xi	2.4940
Zn1···H11C	3.6151	H3···Zn1^ix	3.5373
Zn1···H17	3.2996	H3···Cl1^ix	2.8374
Zn1···H22	3.2735	H5···Zn1	3.4174
Zn1···H3^i	3.5372	H5···Cl1	2.9083
Cl1···C5	3.477 (3)	H5···N1	2.9315
Cl1···C16^ii	3.528 (2)	H5···C15^ii	3.0066
Cl1···C23^iii	3.602 (3)	H5···H11C	2.5481
Cl1···H16^ii	3.0095	H8A···C14	3.0800
Cl1···H21	3.0911	H8B···C11	2.8425
Cl1···H5	2.9083	H8B···C12	2.8626
Cl1···H23B^iii	2.7873	H8B···H11B	2.2862
Cl1···H24A^iii	3.1061	H8B···H12B	2.3241
Cl1···H3^i	2.8374	H8B···Cl2^xii	2.8668
Cl2···H17	3.0996	H9···H12A	2.4557
Cl2···H8B^iv	2.8668	H10···Zn1	3.0848
S1···O1	3.3946 (17)	H11A···H12C	2.5053
S1···O2	3.3056 (16)	H11A···C20^i	2.8955
O1···S1	3.3946 (17)	H11A···C21^i	2.9557
O1···C11	3.398 (3)	H11A···C24^i	3.0435
O1···C13	3.272 (3)	H11A···H20A^i	2.4588
O2···C23	3.309 (4)	H11A···H21^i	2.4012
O2···S1	3.3056 (16)	H11A···H24B^i	2.5402
O2···C1	3.201 (3)	H11B···C8	2.7541
O1···H14^v	2.8082	H11B···H8B	2.2862
O2···H12A^vi	2.9051	H11B···H12B	2.5597
N1···C18	3.178 (3)	H11C···Zn1	3.6151
N2···C6	3.268 (3)	H11C···N1	2.5839
N1···H5	2.9315	H11C···C7	2.8467
N1···H11C	2.5839	H11C···H5	2.5481
N2···H17	2.8312	H11C···H15^ii	2.5912
N2···H23A	2.5629	H12A···H9	2.4557
C1···O2	3.201 (3)	H12A···O2^xiii	2.9051
C1···C19	3.046 (3)	H12B···C8	2.8941
C5···Cl1	3.477 (3)	H12B···H8B	2.3241
C5···Zn1	3.650 (3)	H12B···H11B	2.5597
C6···N2	3.268 (3)	H12B···H22^xii	2.5775
C6···C19	3.206 (3)	H12C···H11A	2.5053
C6···C18	3.445 (3)	H14···O1^xiv	2.8082
C7···C11	3.301 (4)	H14···C1^xiv	2.8374
C7···C13	3.029 (3)	H14···C6^xiv	2.7290
C7···C18	3.193 (3)	H15···H11C^vii	2.5912
C7···C19	3.448 (3)	H16···Cl1^vii	3.0095
C11···Zn1	4.136 (3)	H16···H20A^xiii	2.5017
C11···O1	3.398 (3)	H17···Zn1	3.2996
C11···C7	3.301 (4)	H17···Cl2	3.0996
C13···C7	3.029 (3)	H17···N2	2.8312
C13···O1	3.272 (3)	H17···H23A	2.5797
C16···Cl1^vii	3.528 (2)	H20A···C2	2.9667
C17···Zn1	3.556 (2)	H20A···H11A^ix	2.4588
C18···N1	3.178 (3)	H20A···H16^vi	2.5017
C18···C7	3.193 (3)	H20B···C23	2.8593
C18···C6	3.445 (3)	H20B···C24	2.8453
C19···C23	3.258 (4)	H20B···H23C	2.3338
C19···C1	3.046 (3)	H20B···H24C	2.2878
C19···C7	3.448 (3)	H21···Cl1	3.0911
C19···C6	3.206 (3)	H21···H24B	2.4824
C23···C19	3.258 (4)	H21···H11A^ix	2.4012
C23···O2	3.309 (4)	H22···Zn1	3.2735
C23···Cl1^viii	3.602 (3)	H22···H12B^iv	2.5775
C1···H14^v	2.8374	H23A···N2	2.5629
C2···H20A	2.9667	H23A···C19	2.7342
C6···H14^v	2.7290	H23A···H17	2.5797
C7···H11C	2.8467	H23B···H24A	2.5104
C8···H12B	2.8941	H23B···Cl1^viii	2.7873
C8···H11B	2.7541	H23C···C20	2.7824
C11···H8B	2.8425	H23C···H20B	2.3338
C12···H8B	2.8626	H23C···H24C	2.5096
C14···H8A	3.0800	H24A···H23B	2.5104
C15···H5^vii	3.0066	H24A···Cl1^viii	3.1061
C19···H23A	2.7342	H24B···H21	2.4824
C20···H24C	2.8781	H24B···H11A^ix	2.5402
C20···H11A^ix	2.8955	H24C···C20	2.8781
C20···H23C	2.7824	H24C···H20B	2.2878
C21···H11A^ix	2.9557	H24C···H23C	2.5096
C23···H20B	2.8593	H24C···H2^x	2.4940
Cl1—Zn1—Cl2	116.70 (3)	C3—C4—H4	120.35
Cl1—Zn1—N1	109.53 (6)	C5—C4—H4	120.42
Cl1—Zn1—N2	106.50 (6)	C4—C5—H5	119.53
Cl2—Zn1—N1	109.46 (5)	C6—C5—H5	119.57
Cl2—Zn1—N2	113.56 (6)	O1—C8—H8A	110.88
N1—Zn1—N2	99.70 (7)	O1—C8—H8B	110.90
C1—S1—C13	105.86 (10)	C9—C8—H8A	110.88
C7—O1—C8	105.73 (15)	C9—C8—H8B	110.91
C19—O2—C20	105.81 (17)	H8A—C8—H8B	108.92
Zn1—N1—C7	129.45 (14)	N1—C9—H9	109.67
Zn1—N1—C9	122.41 (12)	C8—C9—H9	109.64
C7—N1—C9	108.11 (16)	C10—C9—H9	109.67
Zn1—N2—C19	128.39 (15)	C9—C10—H10	107.40
Zn1—N2—C21	123.04 (13)	C11—C10—H10	107.41
C19—N2—C21	107.90 (17)	C12—C10—H10	107.39
S1—C1—C2	115.25 (19)	C10—C11—H11A	109.45
S1—C1—C6	125.44 (18)	C10—C11—H11B	109.49
C2—C1—C6	119.2 (2)	C10—C11—H11C	109.44
C1—C2—C3	120.6 (3)	H11A—C11—H11B	109.51
C2—C3—C4	120.6 (3)	H11A—C11—H11C	109.49
C3—C4—C5	119.2 (3)	H11B—C11—H11C	109.45
C4—C5—C6	120.9 (3)	C10—C12—H12A	109.48
C1—C6—C5	119.3 (2)	C10—C12—H12B	109.50
C1—C6—C7	123.93 (19)	C10—C12—H12C	109.48
C5—C6—C7	116.7 (2)	H12A—C12—H12B	109.28
O1—C7—N1	118.05 (18)	H12A—C12—H12C	109.41
O1—C7—C6	116.39 (17)	H12B—C12—H12C	109.68
N1—C7—C6	125.42 (18)	C13—C14—H14	119.41
O1—C8—C9	104.32 (17)	C15—C14—H14	119.43
N1—C9—C8	102.29 (16)	C14—C15—H15	119.94
N1—C9—C10	109.06 (16)	C16—C15—H15	119.81
C8—C9—C10	116.18 (18)	C15—C16—H16	120.19
C9—C10—C11	112.3 (2)	C17—C16—H16	120.29
C9—C10—C12	110.81 (18)	C16—C17—H17	119.66
C11—C10—C12	111.2 (2)	C18—C17—H17	119.68
S1—C13—C14	116.1 (2)	O2—C20—H20A	110.90
S1—C13—C18	125.32 (18)	O2—C20—H20B	110.88
C14—C13—C18	118.5 (2)	C21—C20—H20A	110.82
C13—C14—C15	121.2 (3)	C21—C20—H20B	110.86
C14—C15—C16	120.3 (3)	H20A—C20—H20B	108.89
C15—C16—C17	119.5 (3)	N2—C21—H21	109.70
C16—C17—C18	120.7 (2)	C20—C21—H21	109.70
C13—C18—C17	119.8 (2)	C22—C21—H21	109.72
C13—C18—C19	123.5 (2)	C21—C22—H22	107.64
C17—C18—C19	116.66 (18)	C23—C22—H22	107.67
O2—C19—N2	117.31 (19)	C24—C22—H22	107.65
O2—C19—C18	117.67 (18)	C22—C23—H23A	109.44
N2—C19—C18	124.9 (2)	C22—C23—H23B	109.48
O2—C20—C21	104.46 (17)	C22—C23—H23C	109.48
N2—C21—C20	101.71 (16)	H23A—C23—H23B	109.52
N2—C21—C22	109.60 (16)	H23A—C23—H23C	109.46
C20—C21—C22	116.07 (18)	H23B—C23—H23C	109.45
C21—C22—C23	112.2 (2)	C22—C24—H24A	109.53
C21—C22—C24	110.94 (19)	C22—C24—H24B	109.52
C23—C22—C24	110.5 (2)	C22—C24—H24C	109.48
C1—C2—H2	119.75	H24A—C24—H24B	109.46
C3—C2—H2	119.66	H24A—C24—H24C	109.44
C2—C3—H3	119.67	H24B—C24—H24C	109.40
C4—C3—H3	119.70
Cl1—Zn1—N1—C7	74.1 (2)	S1—C1—C6—C5	−176.89 (18)
Cl1—Zn1—N1—C9	−108.23 (15)	C2—C1—C6—C5	−0.2 (3)
Cl2—Zn1—N1—C7	−156.81 (18)	C2—C1—C6—C7	177.8 (2)
Cl2—Zn1—N1—C9	20.90 (16)	S1—C1—C6—C7	1.1 (3)
N2—Zn1—N1—C7	−37.4 (2)	C1—C2—C3—C4	3.4 (4)
N2—Zn1—N1—C9	140.28 (15)	C2—C3—C4—C5	−1.3 (5)
Cl1—Zn1—N2—C19	−143.23 (17)	C3—C4—C5—C6	−1.5 (4)
Cl1—Zn1—N2—C21	26.24 (15)	C4—C5—C6—C1	2.2 (4)
Cl2—Zn1—N2—C19	86.95 (18)	C4—C5—C6—C7	−175.9 (2)
Cl2—Zn1—N2—C21	−103.58 (15)	C5—C6—C7—O1	112.6 (2)
N1—Zn1—N2—C19	−29.4 (2)	C1—C6—C7—O1	−65.4 (3)
N1—Zn1—N2—C21	140.10 (15)	C1—C6—C7—N1	118.9 (2)
C13—S1—C1—C2	142.85 (18)	C5—C6—C7—N1	−63.1 (3)
C13—S1—C1—C6	−40.3 (2)	O1—C8—C9—C10	106.7 (2)
C1—S1—C13—C14	139.5 (2)	O1—C8—C9—N1	−11.9 (2)
C1—S1—C13—C18	−42.9 (2)	C8—C9—C10—C11	−55.7 (3)
C8—O1—C7—N1	−3.9 (3)	N1—C9—C10—C11	59.2 (2)
C8—O1—C7—C6	−179.89 (18)	C8—C9—C10—C12	69.4 (3)
C7—O1—C8—C9	10.0 (2)	N1—C9—C10—C12	−175.68 (19)
C20—O2—C19—N2	−5.8 (2)	C18—C13—C14—C15	−0.2 (4)
C20—O2—C19—C18	177.59 (18)	S1—C13—C18—C17	179.94 (18)
C19—O2—C20—C21	13.9 (2)	S1—C13—C14—C15	177.6 (2)
Zn1—N1—C7—C6	−10.9 (3)	C14—C13—C18—C17	−2.5 (4)
C9—N1—C7—O1	−4.4 (3)	C14—C13—C18—C19	179.5 (2)
C9—N1—C7—C6	171.17 (18)	S1—C13—C18—C19	1.9 (3)
Zn1—N1—C9—C8	−167.93 (15)	C13—C14—C15—C16	1.8 (5)
Zn1—N1—C7—O1	173.52 (15)	C14—C15—C16—C17	−0.6 (4)
Zn1—N1—C9—C10	68.5 (2)	C15—C16—C17—C18	−2.1 (4)
C7—N1—C9—C8	10.2 (2)	C16—C17—C18—C13	3.7 (4)
C7—N1—C9—C10	−113.37 (19)	C16—C17—C18—C19	−178.2 (2)
Zn1—N2—C19—C18	−18.5 (3)	C13—C18—C19—O2	−60.3 (3)
C21—N2—C19—O2	−5.6 (2)	C13—C18—C19—N2	123.4 (3)
C21—N2—C19—C18	170.78 (18)	C17—C18—C19—N2	−54.7 (3)
Zn1—N2—C19—O2	165.18 (14)	C17—C18—C19—O2	121.6 (2)
C19—N2—C21—C22	−109.8 (2)	O2—C20—C21—C22	102.5 (2)
Zn1—N2—C21—C20	−157.75 (14)	O2—C20—C21—N2	−16.3 (2)
Zn1—N2—C21—C22	78.9 (2)	N2—C21—C22—C23	59.8 (2)
C19—N2—C21—C20	13.6 (2)	C20—C21—C22—C23	−54.6 (3)
S1—C1—C2—C3	174.4 (2)	C20—C21—C22—C24	69.5 (3)
C6—C1—C2—C3	−2.6 (4)	N2—C21—C22—C24	−176.04 (19)

Symmetry codes: (i) −x+2, y+1/2, −z+3/2; (ii) x+1, y, z; (iii) x+1/2, −y+3/2, −z+2; (iv) −x+3/2, −y+2, z+1/2; (v) x+1/2, −y+3/2, −z+1; (vi) −x+1, y−1/2, −z+3/2; (vii) x−1, y, z; (viii) x−1/2, −y+3/2, −z+2; (ix) −x+2, y−1/2, −z+3/2; (x) −x+3/2, −y+1, z+1/2; (xi) −x+3/2, −y+1, z−1/2; (xii) −x+3/2, −y+2, z−1/2; (xiii) −x+1, y+1/2, −z+3/2; (xiv) x−1/2, −y+3/2, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11C···N1	0.98	2.58	2.940 (4)	101
C23—H23A···N2	0.98	2.56	2.953 (4)	104
C23—H23B···Cl1^viii	0.98	2.79	3.602 (3)	141

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