(μ-1,2-Di-4-pyridylethyl-ene-κN:N')bis-[bis-(N,N-dimethyl-dithio-carbamato-κS,S')zinc(II)].

The dinuclear title compound, [Zn(2)(C(3)H(6)NS(2))(4)(C(12)H(10)N(2))], features two five-coordinate Zn atoms, one with an NS(4) coordination geometry distorted towards a trigonal-bipyramidal arrangement, and the other distorted towards a square pyramid. In the crystal, mol-ecules are connected into supra-molecular zigzag chains via C-H⋯S contacts. Chains are connected via C-H⋯π interactions, consolidating the crystal packing.

Related literature

For background to supra­molecular polymers of zinc 1,1-dithiol­ates, see: Lai et al. (2002 ▶); Chen et al. (2006 ▶); Benson et al. (2007 ▶). For a related structure and the synthesis, see: Lai & Tiekink (2003 ▶). For additional geometrical analysis, see: Addison et al. (1984 ▶).

Experimental

Crystal data

[Zn2(C3H6NS2)4(C12H10N2)]

M = 793.79

Monoclinic,

a = 13.061 (4) Å

b = 15.904 (4) Å

c = 17.658 (5) Å

β = 108.443 (4)°

V = 3479.7 (16) Å3

Z = 4

Mo Kα radiation

μ = 1.88 mm−1

T = 98 K

0.40 × 0.08 × 0.06 mm

Data collection

Rigaku AFC12K/SATURN724 diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.645, T max = 1.000

23158 measured reflections

7142 independent reflections

6509 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.155

S = 1.22

7142 reflections

369 parameters

H-atom parameters constrained

Δρmax = 1.51 e Å−3

Δρmin = −0.73 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809044249/pv2225sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044249/pv2225Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Zn2(C3H6NS2)4(C12H10N2)]	F(000) = 1632
Mr = 793.79	Dx = 1.515 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 17793 reflections
a = 13.061 (4) Å	θ = 2.1–40.7°
b = 15.904 (4) Å	µ = 1.88 mm−1
c = 17.658 (5) Å	T = 98 K
β = 108.443 (4)°	Prism, pale-yellow
V = 3479.7 (16) Å3	0.40 × 0.08 × 0.06 mm
Z = 4

Rigaku AFC12K/SATURN724 diffractometer	7142 independent reflections
Radiation source: fine-focus sealed tube	6509 reflections with I > 2σ(I)
graphite	Rint = 0.048
ω scans	θmax = 26.5°, θmin = 2.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −14→16
Tmin = 0.645, Tmax = 1	k = −19→19
23158 measured reflections	l = −22→22

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155	H-atom parameters constrained
S = 1.22	w = 1/[σ2(Fo2) + (0.0348P)2 + 22.73P] where P = (Fo2 + 2Fc2)/3
7142 reflections	(Δ/σ)max = 0.001
369 parameters	Δρmax = 1.51 e Å−3
0 restraints	Δρmin = −0.73 e Å−3

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 F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Zn1	1.20505 (5)	−0.06078 (4)	0.25194 (4)	0.01739 (16)
Zn2	0.28728 (5)	0.32085 (4)	0.25404 (3)	0.01633 (15)
S1	1.36946 (11)	−0.05320 (9)	0.35297 (8)	0.0220 (3)
S2	1.19681 (11)	−0.16805 (9)	0.36581 (8)	0.0231 (3)
S3	1.13226 (12)	−0.14634 (9)	0.13829 (8)	0.0249 (3)
S4	1.23185 (12)	0.02060 (10)	0.13722 (9)	0.0270 (3)
S5	0.12699 (11)	0.30053 (9)	0.14792 (8)	0.0217 (3)
S6	0.29923 (11)	0.41474 (9)	0.13505 (8)	0.0219 (3)
S7	0.36844 (12)	0.41455 (8)	0.36276 (8)	0.0212 (3)
S8	0.24259 (12)	0.26126 (9)	0.37027 (8)	0.0235 (3)
N1	1.3939 (4)	−0.1618 (3)	0.4724 (3)	0.0263 (11)
N2	1.1227 (4)	−0.0632 (4)	0.0052 (3)	0.0313 (12)
N3	1.0784 (3)	0.0114 (3)	0.2611 (2)	0.0162 (9)
N4	0.4200 (3)	0.2477 (3)	0.2579 (3)	0.0166 (9)
N5	0.1104 (4)	0.3966 (3)	0.0203 (3)	0.0297 (11)
N6	0.3653 (4)	0.3445 (3)	0.4985 (3)	0.0268 (11)
C1	1.3264 (5)	−0.1315 (3)	0.4054 (3)	0.0215 (11)
C2	1.3594 (6)	−0.2265 (5)	0.5182 (4)	0.0422 (17)
H2A	1.3048	−0.2031	0.5395	0.063*
H2B	1.4217	−0.2456	0.5623	0.063*
H2C	1.3287	−0.2743	0.4832	0.063*
C3	1.5023 (5)	−0.1256 (5)	0.5090 (4)	0.0394 (16)
H3A	1.5345	−0.1125	0.4672	0.059*
H3B	1.5480	−0.1663	0.5464	0.059*
H3C	1.4966	−0.0740	0.5377	0.059*
C4	1.1581 (5)	−0.0622 (4)	0.0845 (3)	0.0237 (12)
C5	1.0612 (7)	−0.1339 (5)	−0.0405 (4)	0.0448 (18)
H5A	1.1110	−0.1749	−0.0511	0.067*
H5B	1.0118	−0.1132	−0.0912	0.067*
H5C	1.0196	−0.1608	−0.0097	0.067*
C6	1.1407 (6)	0.0060 (5)	−0.0437 (4)	0.0405 (17)
H6A	1.1687	0.0549	−0.0096	0.061*
H6B	1.0723	0.0209	−0.0842	0.061*
H6C	1.1930	−0.0113	−0.0700	0.061*
C7	0.9896 (4)	−0.0291 (3)	0.2653 (3)	0.0205 (11)
H7	0.9906	−0.0888	0.2679	0.025*
C8	0.8978 (4)	0.0128 (3)	0.2659 (3)	0.0195 (11)
H8	0.8369	−0.0181	0.2689	0.023*
C9	0.8936 (4)	0.1001 (3)	0.2622 (3)	0.0155 (10)
C10	0.9858 (4)	0.1419 (3)	0.2589 (3)	0.0187 (10)
H10	0.9873	0.2015	0.2576	0.022*
C11	1.0749 (4)	0.0960 (3)	0.2577 (3)	0.0172 (10)
H11	1.1366	0.1255	0.2544	0.021*
C12	0.7970 (4)	0.1474 (3)	0.2610 (3)	0.0171 (10)
H12	0.8001	0.2070	0.2581	0.020*
C13	0.7048 (4)	0.1132 (3)	0.2637 (3)	0.0203 (11)
H13	0.7021	0.0536	0.2672	0.024*
C14	0.6081 (4)	0.1601 (3)	0.2616 (3)	0.0188 (11)
C15	0.5180 (4)	0.1187 (3)	0.2703 (3)	0.0206 (11)
H15	0.5195	0.0595	0.2777	0.025*
C16	0.4266 (4)	0.1642 (3)	0.2681 (3)	0.0200 (11)
H16	0.3661	0.1350	0.2741	0.024*
C17	0.5068 (4)	0.2883 (3)	0.2503 (4)	0.0221 (11)
H17	0.5032	0.3477	0.2437	0.027*
C18	0.6004 (4)	0.2477 (3)	0.2516 (3)	0.0202 (11)
H18	0.6595	0.2788	0.2457	0.024*
C19	0.3290 (4)	0.3405 (3)	0.4199 (3)	0.0202 (11)
C20	0.3321 (7)	0.2847 (4)	0.5497 (4)	0.0415 (18)
H20A	0.2795	0.2451	0.5163	0.062*
H20B	0.2993	0.3154	0.5843	0.062*
H20C	0.3954	0.2537	0.5827	0.062*
C21	0.4428 (6)	0.4077 (4)	0.5421 (4)	0.0378 (16)
H21A	0.4786	0.4328	0.5064	0.057*
H21B	0.4969	0.3811	0.5874	0.057*
H21C	0.4049	0.4516	0.5617	0.057*
C22	0.1729 (4)	0.3733 (3)	0.0934 (3)	0.0198 (11)
C23	0.0051 (6)	0.3582 (5)	−0.0177 (4)	0.0414 (17)
H23A	0.0144	0.3056	−0.0438	0.062*
H23B	−0.0401	0.3969	−0.0577	0.062*
H23C	−0.0298	0.3463	0.0228	0.062*
C24	0.1514 (6)	0.4526 (5)	−0.0292 (4)	0.0407 (17)
H24A	0.1989	0.4948	0.0047	0.061*
H24B	0.0907	0.4807	−0.0685	0.061*
H24C	0.1920	0.4197	−0.0571	0.061*

	U11	U22	U33	U12	U13	U23
Zn1	0.0141 (3)	0.0210 (3)	0.0169 (3)	0.0026 (2)	0.0046 (2)	−0.0017 (2)
Zn2	0.0149 (3)	0.0178 (3)	0.0163 (3)	0.0025 (2)	0.0051 (2)	−0.0006 (2)
S1	0.0173 (6)	0.0239 (7)	0.0221 (7)	−0.0011 (5)	0.0025 (5)	−0.0001 (5)
S2	0.0225 (7)	0.0234 (7)	0.0220 (7)	−0.0002 (5)	0.0050 (5)	0.0024 (5)
S3	0.0322 (8)	0.0199 (7)	0.0203 (7)	0.0009 (6)	0.0049 (6)	−0.0016 (5)
S4	0.0298 (8)	0.0309 (8)	0.0222 (7)	−0.0065 (6)	0.0110 (6)	−0.0001 (6)
S5	0.0188 (7)	0.0251 (7)	0.0195 (7)	0.0007 (5)	0.0038 (5)	−0.0004 (5)
S6	0.0241 (7)	0.0219 (7)	0.0198 (7)	0.0013 (5)	0.0071 (5)	−0.0004 (5)
S7	0.0290 (7)	0.0187 (6)	0.0175 (6)	−0.0041 (5)	0.0097 (5)	0.0004 (5)
S8	0.0244 (7)	0.0258 (7)	0.0224 (7)	−0.0087 (6)	0.0102 (6)	−0.0022 (5)
N1	0.025 (3)	0.027 (3)	0.022 (2)	−0.001 (2)	0.000 (2)	0.000 (2)
N2	0.034 (3)	0.038 (3)	0.019 (2)	0.007 (2)	0.005 (2)	0.002 (2)
N3	0.013 (2)	0.019 (2)	0.015 (2)	0.0025 (17)	0.0028 (16)	0.0002 (17)
N4	0.017 (2)	0.014 (2)	0.019 (2)	0.0017 (17)	0.0058 (17)	0.0012 (17)
N5	0.032 (3)	0.034 (3)	0.019 (2)	−0.001 (2)	0.002 (2)	0.002 (2)
N6	0.039 (3)	0.027 (3)	0.014 (2)	−0.012 (2)	0.008 (2)	0.0019 (19)
C1	0.026 (3)	0.021 (3)	0.017 (3)	0.002 (2)	0.006 (2)	−0.001 (2)
C2	0.047 (4)	0.045 (4)	0.025 (3)	−0.005 (3)	−0.001 (3)	0.012 (3)
C3	0.029 (3)	0.047 (4)	0.031 (3)	−0.008 (3)	−0.008 (3)	0.004 (3)
C4	0.022 (3)	0.031 (3)	0.017 (3)	0.006 (2)	0.006 (2)	0.001 (2)
C5	0.060 (5)	0.046 (4)	0.021 (3)	0.000 (4)	0.003 (3)	−0.007 (3)
C6	0.043 (4)	0.056 (5)	0.022 (3)	0.000 (3)	0.010 (3)	0.008 (3)
C7	0.019 (3)	0.018 (3)	0.027 (3)	0.004 (2)	0.011 (2)	0.003 (2)
C8	0.018 (3)	0.015 (2)	0.026 (3)	−0.002 (2)	0.008 (2)	0.001 (2)
C9	0.019 (3)	0.014 (2)	0.013 (2)	−0.0002 (19)	0.0041 (19)	−0.0012 (18)
C10	0.019 (3)	0.013 (2)	0.025 (3)	0.001 (2)	0.007 (2)	0.002 (2)
C11	0.014 (2)	0.014 (2)	0.023 (3)	−0.0008 (19)	0.006 (2)	0.000 (2)
C12	0.017 (3)	0.014 (2)	0.021 (3)	−0.0019 (19)	0.006 (2)	−0.0005 (19)
C13	0.020 (3)	0.014 (2)	0.027 (3)	0.000 (2)	0.008 (2)	0.006 (2)
C14	0.017 (3)	0.018 (3)	0.020 (3)	0.000 (2)	0.004 (2)	0.002 (2)
C15	0.021 (3)	0.017 (3)	0.025 (3)	−0.002 (2)	0.009 (2)	0.005 (2)
C16	0.022 (3)	0.017 (3)	0.022 (3)	−0.003 (2)	0.009 (2)	0.001 (2)
C17	0.018 (3)	0.013 (2)	0.036 (3)	−0.002 (2)	0.010 (2)	0.000 (2)
C18	0.020 (3)	0.014 (2)	0.028 (3)	−0.003 (2)	0.010 (2)	0.002 (2)
C19	0.021 (3)	0.020 (3)	0.022 (3)	0.001 (2)	0.009 (2)	0.001 (2)
C20	0.072 (5)	0.031 (3)	0.026 (3)	−0.019 (3)	0.022 (3)	0.005 (3)
C21	0.052 (4)	0.040 (4)	0.020 (3)	−0.018 (3)	0.010 (3)	−0.005 (3)
C22	0.021 (3)	0.021 (3)	0.016 (3)	0.005 (2)	0.004 (2)	−0.002 (2)
C23	0.037 (4)	0.053 (4)	0.022 (3)	−0.002 (3)	−0.007 (3)	0.008 (3)
C24	0.048 (4)	0.045 (4)	0.025 (3)	−0.001 (3)	0.005 (3)	0.011 (3)

Zn1—N3	2.061 (4)	C5—H5A	0.9800
Zn1—S1	2.3204 (15)	C5—H5B	0.9800
Zn1—S3	2.3613 (16)	C5—H5C	0.9800
Zn1—S4	2.5200 (16)	C6—H6A	0.9800
Zn1—S2	2.6650 (16)	C6—H6B	0.9800
Zn2—N4	2.071 (4)	C6—H6C	0.9800
Zn2—S5	2.3488 (15)	C7—C8	1.376 (7)
Zn2—S7	2.3964 (15)	C7—H7	0.9500
Zn2—S8	2.4918 (16)	C8—C9	1.391 (7)
Zn2—S6	2.6223 (16)	C8—H8	0.9500
S1—C1	1.746 (6)	C9—C10	1.391 (7)
S2—C1	1.716 (6)	C9—C12	1.463 (7)
S3—C4	1.736 (6)	C10—C11	1.380 (7)
S4—C4	1.721 (6)	C10—H10	0.9500
S5—C22	1.730 (6)	C11—H11	0.9500
S6—C22	1.711 (6)	C12—C13	1.336 (7)
S7—C19	1.732 (6)	C12—H12	0.9500
S8—C19	1.733 (6)	C13—C14	1.458 (7)
N1—C1	1.323 (7)	C13—H13	0.9500
N1—C2	1.466 (8)	C14—C15	1.399 (7)
N1—C3	1.475 (8)	C14—C18	1.403 (7)
N2—C4	1.328 (7)	C15—C16	1.387 (8)
N2—C6	1.463 (9)	C15—H15	0.9500
N2—C5	1.466 (9)	C16—H16	0.9500
N3—C11	1.348 (7)	C17—C18	1.377 (8)
N3—C7	1.348 (7)	C17—H17	0.9500
N4—C16	1.339 (7)	C18—H18	0.9500
N4—C17	1.349 (7)	C20—H20A	0.9800
N5—C22	1.343 (7)	C20—H20B	0.9800
N5—C23	1.460 (8)	C20—H20C	0.9800
N5—C24	1.463 (8)	C21—H21A	0.9800
N6—C19	1.319 (7)	C21—H21B	0.9800
N6—C21	1.460 (8)	C21—H21C	0.9800
N6—C20	1.470 (7)	C23—H23A	0.9800
C2—H2A	0.9800	C23—H23B	0.9800
C2—H2B	0.9800	C23—H23C	0.9800
C2—H2C	0.9800	C24—H24A	0.9800
C3—H3A	0.9800	C24—H24B	0.9800
C3—H3B	0.9800	C24—H24C	0.9800
C3—H3C	0.9800
N3—Zn1—S1	118.77 (13)	N2—C6—H6B	109.5
N3—Zn1—S3	105.66 (13)	H6A—C6—H6B	109.5
S1—Zn1—S3	135.17 (6)	N2—C6—H6C	109.5
N3—Zn1—S4	95.51 (13)	H6A—C6—H6C	109.5
S1—Zn1—S4	105.14 (6)	H6B—C6—H6C	109.5
S3—Zn1—S4	74.56 (6)	N3—C7—C8	122.5 (5)
N3—Zn1—S2	94.15 (13)	N3—C7—H7	118.8
S1—Zn1—S2	72.64 (5)	C8—C7—H7	118.8
S3—Zn1—S2	99.84 (6)	C7—C8—C9	120.3 (5)
S4—Zn1—S2	169.86 (5)	C7—C8—H8	119.9
N4—Zn2—S5	118.30 (13)	C9—C8—H8	119.9
N4—Zn2—S7	99.78 (13)	C8—C9—C10	117.2 (5)
S5—Zn2—S7	141.40 (6)	C8—C9—C12	122.3 (5)
N4—Zn2—S8	99.85 (13)	C10—C9—C12	120.5 (5)
S5—Zn2—S8	102.88 (6)	C11—C10—C9	119.6 (5)
S7—Zn2—S8	74.71 (5)	C11—C10—H10	120.2
N4—Zn2—S6	94.87 (12)	C9—C10—H10	120.2
S5—Zn2—S6	72.73 (5)	N3—C11—C10	123.0 (5)
S7—Zn2—S6	99.46 (5)	N3—C11—H11	118.5
S8—Zn2—S6	164.88 (5)	C10—C11—H11	118.5
C1—S1—Zn1	89.75 (19)	C13—C12—C9	124.9 (5)
C1—S2—Zn1	79.62 (19)	C13—C12—H12	117.5
C4—S3—Zn1	85.7 (2)	C9—C12—H12	117.5
C4—S4—Zn1	81.14 (19)	C12—C13—C14	125.0 (5)
C22—S5—Zn2	88.47 (19)	C12—C13—H13	117.5
C22—S6—Zn2	80.31 (19)	C14—C13—H13	117.5
C19—S7—Zn2	84.58 (19)	C15—C14—C18	116.9 (5)
C19—S8—Zn2	81.66 (18)	C15—C14—C13	120.5 (5)
C1—N1—C2	121.0 (5)	C18—C14—C13	122.6 (5)
C1—N1—C3	121.7 (5)	C16—C15—C14	119.8 (5)
C2—N1—C3	116.9 (5)	C16—C15—H15	120.1
C4—N2—C6	123.0 (6)	C14—C15—H15	120.1
C4—N2—C5	122.4 (6)	N4—C16—C15	122.7 (5)
C6—N2—C5	114.5 (5)	N4—C16—H16	118.7
C11—N3—C7	117.5 (5)	C15—C16—H16	118.7
C11—N3—Zn1	124.7 (4)	N4—C17—C18	122.9 (5)
C7—N3—Zn1	117.7 (4)	N4—C17—H17	118.6
C16—N4—C17	118.0 (5)	C18—C17—H17	118.6
C16—N4—Zn2	125.4 (4)	C17—C18—C14	119.8 (5)
C17—N4—Zn2	116.6 (4)	C17—C18—H18	120.1
C22—N5—C23	121.7 (5)	C14—C18—H18	120.1
C22—N5—C24	121.0 (5)	N6—C19—S7	120.3 (4)
C23—N5—C24	116.7 (5)	N6—C19—S8	121.9 (4)
C19—N6—C21	123.2 (5)	S7—C19—S8	117.8 (3)
C19—N6—C20	122.5 (5)	N6—C20—H20A	109.5
C21—N6—C20	114.3 (5)	N6—C20—H20B	109.5
N1—C1—S2	122.2 (4)	H20A—C20—H20B	109.5
N1—C1—S1	119.9 (4)	N6—C20—H20C	109.5
S2—C1—S1	117.9 (3)	H20A—C20—H20C	109.5
N1—C2—H2A	109.5	H20B—C20—H20C	109.5
N1—C2—H2B	109.5	N6—C21—H21A	109.5
H2A—C2—H2B	109.5	N6—C21—H21B	109.5
N1—C2—H2C	109.5	H21A—C21—H21B	109.5
H2A—C2—H2C	109.5	N6—C21—H21C	109.5
H2B—C2—H2C	109.5	H21A—C21—H21C	109.5
N1—C3—H3A	109.5	H21B—C21—H21C	109.5
N1—C3—H3B	109.5	N5—C22—S6	121.2 (4)
H3A—C3—H3B	109.5	N5—C22—S5	120.4 (4)
N1—C3—H3C	109.5	S6—C22—S5	118.4 (3)
H3A—C3—H3C	109.5	N5—C23—H23A	109.5
H3B—C3—H3C	109.5	N5—C23—H23B	109.5
N2—C4—S4	121.9 (5)	H23A—C23—H23B	109.5
N2—C4—S3	120.3 (5)	N5—C23—H23C	109.5
S4—C4—S3	117.8 (3)	H23A—C23—H23C	109.5
N2—C5—H5A	109.5	H23B—C23—H23C	109.5
N2—C5—H5B	109.5	N5—C24—H24A	109.5
H5A—C5—H5B	109.5	N5—C24—H24B	109.5
N2—C5—H5C	109.5	H24A—C24—H24B	109.5
H5A—C5—H5C	109.5	N5—C24—H24C	109.5
H5B—C5—H5C	109.5	H24A—C24—H24C	109.5
N2—C6—H6A	109.5	H24B—C24—H24C	109.5
N3—Zn1—S1—C1	87.2 (2)	Zn1—S2—C1—S1	3.1 (3)
S3—Zn1—S1—C1	−84.5 (2)	Zn1—S1—C1—N1	175.1 (5)
S4—Zn1—S1—C1	−167.63 (19)	Zn1—S1—C1—S2	−3.5 (3)
S2—Zn1—S1—C1	2.06 (18)	C6—N2—C4—S4	−1.6 (9)
N3—Zn1—S2—C1	−121.0 (2)	C5—N2—C4—S4	179.1 (5)
S1—Zn1—S2—C1	−2.13 (19)	C6—N2—C4—S3	179.3 (5)
S3—Zn1—S2—C1	132.29 (19)	C5—N2—C4—S3	−0.1 (9)
S4—Zn1—S2—C1	76.7 (4)	Zn1—S4—C4—N2	172.6 (5)
N3—Zn1—S3—C4	86.0 (2)	Zn1—S4—C4—S3	−8.2 (3)
S1—Zn1—S3—C4	−101.6 (2)	Zn1—S3—C4—N2	−172.1 (5)
S4—Zn1—S3—C4	−5.44 (19)	Zn1—S3—C4—S4	8.7 (3)
S2—Zn1—S3—C4	−176.78 (19)	C11—N3—C7—C8	0.2 (8)
N3—Zn1—S4—C4	−99.2 (2)	Zn1—N3—C7—C8	−175.4 (4)
S1—Zn1—S4—C4	139.0 (2)	N3—C7—C8—C9	0.0 (8)
S3—Zn1—S4—C4	5.5 (2)	C7—C8—C9—C10	−0.8 (8)
S2—Zn1—S4—C4	63.0 (4)	C7—C8—C9—C12	178.7 (5)
N4—Zn2—S5—C22	−88.2 (2)	C8—C9—C10—C11	1.4 (8)
S7—Zn2—S5—C22	81.4 (2)	C12—C9—C10—C11	−178.1 (5)
S8—Zn2—S5—C22	162.95 (18)	C7—N3—C11—C10	0.4 (8)
S6—Zn2—S5—C22	−2.06 (18)	Zn1—N3—C11—C10	175.7 (4)
N4—Zn2—S6—C22	120.3 (2)	C9—C10—C11—N3	−1.3 (8)
S5—Zn2—S6—C22	2.11 (18)	C8—C9—C12—C13	0.4 (8)
S7—Zn2—S6—C22	−138.96 (18)	C10—C9—C12—C13	179.8 (5)
S8—Zn2—S6—C22	−73.1 (3)	C9—C12—C13—C14	−179.3 (5)
N4—Zn2—S7—C19	−90.9 (2)	C12—C13—C14—C15	−175.5 (5)
S5—Zn2—S7—C19	98.4 (2)	C12—C13—C14—C18	4.0 (9)
S8—Zn2—S7—C19	6.76 (19)	C18—C14—C15—C16	0.6 (8)
S6—Zn2—S7—C19	172.47 (19)	C13—C14—C15—C16	−179.9 (5)
N4—Zn2—S8—C19	90.7 (2)	C17—N4—C16—C15	−0.7 (8)
S5—Zn2—S8—C19	−147.03 (19)	Zn2—N4—C16—C15	−179.8 (4)
S7—Zn2—S8—C19	−6.80 (19)	C14—C15—C16—N4	0.0 (8)
S6—Zn2—S8—C19	−75.8 (3)	C16—N4—C17—C18	0.9 (8)
S1—Zn1—N3—C11	66.9 (4)	Zn2—N4—C17—C18	−179.9 (4)
S3—Zn1—N3—C11	−119.2 (4)	N4—C17—C18—C14	−0.4 (9)
S4—Zn1—N3—C11	−43.7 (4)	C15—C14—C18—C17	−0.4 (8)
S2—Zn1—N3—C11	139.4 (4)	C13—C14—C18—C17	−179.9 (5)
S1—Zn1—N3—C7	−117.8 (4)	C21—N6—C19—S7	−2.6 (9)
S3—Zn1—N3—C7	56.1 (4)	C20—N6—C19—S7	178.3 (5)
S4—Zn1—N3—C7	131.6 (4)	C21—N6—C19—S8	176.5 (5)
S2—Zn1—N3—C7	−45.3 (4)	C20—N6—C19—S8	−2.6 (9)
S5—Zn2—N4—C16	−65.3 (5)	Zn2—S7—C19—N6	168.5 (5)
S7—Zn2—N4—C16	121.2 (4)	Zn2—S7—C19—S8	−10.6 (3)
S8—Zn2—N4—C16	45.2 (4)	Zn2—S8—C19—N6	−168.9 (5)
S6—Zn2—N4—C16	−138.3 (4)	Zn2—S8—C19—S7	10.3 (3)
S5—Zn2—N4—C17	115.6 (4)	C23—N5—C22—S6	176.4 (5)
S7—Zn2—N4—C17	−57.9 (4)	C24—N5—C22—S6	5.4 (8)
S8—Zn2—N4—C17	−133.9 (4)	C23—N5—C22—S5	−3.7 (8)
S6—Zn2—N4—C17	42.6 (4)	C24—N5—C22—S5	−174.8 (5)
C2—N1—C1—S2	−2.5 (8)	Zn2—S6—C22—N5	176.8 (5)
C3—N1—C1—S2	−175.3 (5)	Zn2—S6—C22—S5	−3.1 (3)
C2—N1—C1—S1	179.0 (5)	Zn2—S5—C22—N5	−176.4 (5)
C3—N1—C1—S1	6.2 (8)	Zn2—S5—C22—S6	3.4 (3)
Zn1—S2—C1—N1	−175.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···S6i	0.95	2.81	3.636 (5)	146
C18—H18···Cg1ii	0.95	2.76	3.589 (5)	146
C24—H24b···Cg2iii	0.98	2.93	3.638 (7)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯S6i	0.95	2.81	3.636 (5)	146
C18—H18⋯Cg1ii	0.95	2.76	3.589 (5)	146
C24—H24b⋯Cg2iii	0.98	2.93	3.638 (7)	130

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the Zn, S1, S2, C1 chelate ring and Cg2 is the centroid of the N3, C7–C11 ring.