Bis(μ-N-butyl-N-ethyl­di­thio­carbamato-S:S′)bis­[(N-butyl-N-ethyl­di­thio­carbamato)­zinc(II)]

Baba, I.; Farina, Y.; Kassim, K.; Othman, A.H.; Razak, I.A.; Fun, H.-K.; Ng, S.W.

doi:10.1107/S1600536800020808

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Bis(μ-N-butyl-N-ethyldithiocarbamato-S:S′)bis[(N-butyl-N-ethyldithiocarbamato)zinc(II)]

I. Baba, Y. Farina, K. Kassim, A. H. Othman, I. A. Razak, H.-K. Fun and S. W. Ng

In the title compound, [(C₂H₅)(C₄H₉)NCS₂]₄Zn₂ or [Zn₂(C₇H₁₄NS₂)₄], one dithiocarbamate group chelates the Zn atom whereas the other is bonded to two Zn atoms. The coordination geometry of the Zn atom is a tetrahedron distorted towards a five-coordinate geometry intermediate between trigonal bipyramidal and a square pyramidal.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536800020808/na6028sup1.cif Contains datablocks I, aho49m
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536800020808/na6028Isup2.hkl Contains datablock I

CCDC reference: 159702

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.008 Å
Disorder in main residue
R factor = 0.047
wR factor = 0.144
Data-to-parameter ratio = 26.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_301  Alert C Main residue disorder ........................      15.00 Perc.

PLAT_702  Alert C Angle   Calc   135.55(4), Rep  135.60(10), Dev.      1.25 Sigma
                     S1   -ZN1  -S3      1.555   1.555   1.555

PLAT_732  Alert C Angle   Calc    75.70(3), Rep   75.70(10) ....       3.33 s.u-Ratio
                     S1   -ZN1  -S2      1.555   1.555   1.555

PLAT_732  Alert C Angle   Calc   135.55(4), Rep  135.60(10) ....       2.50 s.u-Ratio
                     S1   -ZN1  -S3      1.555   1.555   1.555

PLAT_732  Alert C Angle   Calc    95.69(3), Rep   95.70(10) ....       3.33 s.u-Ratio
                     S1   -ZN1  -S4      1.555   1.555   1.555

PLAT_732  Alert C Angle   Calc   106.29(4), Rep  106.30(10) ....       2.50 s.u-Ratio
                     S2   -ZN1  -S3      1.555   1.555   1.555

PLAT_732  Alert C Angle   Calc   162.29(4), Rep  162.30(10) ....       2.50 s.u-Ratio
                     S2   -ZN1  -S4      1.555   1.555   1.555

PLAT_732  Alert C Angle   Calc    68.87(3), Rep   68.90(10) ....       3.33 s.u-Ratio
                     S3   -ZN1  -S4      1.555   1.555   1.555

PLAT_733  Alert C Torsion Calc   107.19(4), Rep  107.20(10) ....       2.50 s.u-Ratio
                     S3  -ZN1 -S4  -ZN1    1.555   1.555   1.555   5.566

PLAT_733  Alert C Torsion Calc  -115.88(3), Rep -115.90(10) ....       3.33 s.u-Ratio
                     S1  -ZN1 -S4  -ZN1    1.555   1.555   1.555   5.566

PLAT_733  Alert C Torsion Calc     0.00(4), Rep    0.00(10) ....       2.50 s.u-Ratio
                     S4  -ZN1 -S4  -ZN1    5.566   1.555   1.555   5.566


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 11 Alert Level C = Please check

Comment top

The title compound, (I), adopts a centrosymmetric dimeric structure in which the Zn atom is chelated by one dithiocarbamate anion; the other dithiocarbamate anion uses one of its two S atoms to bind to two Zn atoms through two bonds. The long bond corresponds to the typical values of 2.815 (1)–3.036 (6) Å found in zinc dithiocarbamates (Cox & Tiekink, 1997). The metal coordination geometry is tetrahedral distorted towards five-coordinate intermediate between trigonal bipyramidal and a square pyramidal. The structure is similar to those of diisopropyldithiocarbamate (Miyamae, 1979) and diethyldithiocabramate zinc (Tiekink, 2000).

Experimental top

Carbon disulfide was added to an ethanol solution of butylethylamine at 277 K followed by an ethanol solution of zinc chloride. The mixture was vigorously stirred and then set aside. The solid that separated was isolated and then recrystallized from ethanol to afford the title compound.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Figures top

Fig. 1. ORTEPII (Johnson, 1976) plot of the title compound at the 50% probability level. H atoms are shown as circles of arbitrary radii.

Bis(µ-N-butyl-N-ethyldithiocarbamato-S:S')bis[(N-butyl-N– ethyldithiocarbamato)zinc(II)] top

Crystal data top

[Zn₂(C₇H₁₄NS₂)₄]	D_x = 1.317 Mg m⁻³
M_r = 835.99	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 6367 reflections
a = 14.7301 (2) Å	θ = 1.7–28.2°
b = 12.0254 (2) Å	µ = 1.56 mm⁻¹
c = 23.7960 (1) Å	T = 298 K
V = 4215.11 (9) Å³	Block, colorless
Z = 4	0.46 × 0.24 × 0.20 mm
F(000) = 1760

Data collection top

Siemens CCD area-detectorr diffractometer	5171 independent reflections
Radiation source: fine-focus sealed tube	3106 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.082
Detector resolution: 8.33 pixels mm^-1	θ_max = 28.2°, θ_min = 1.7°
ω scans	h = −17→19
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	k = −14→15
T_min = 0.534, T_max = 0.746	l = −30→31
27642 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.144	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.0802P)²] where P = (F_o² + 2F_c²)/3
5171 reflections	(Δ/σ)_max = 0.001
199 parameters	Δρ_max = 0.39 e Å⁻³
69 restraints	Δρ_min = −0.50 e Å⁻³

Crystal data top

[Zn₂(C₇H₁₄NS₂)₄]	V = 4215.11 (9) Å³
M_r = 835.99	Z = 4
Orthorhombic, Pbca	Mo Kα radiation
a = 14.7301 (2) Å	µ = 1.56 mm⁻¹
b = 12.0254 (2) Å	T = 298 K
c = 23.7960 (1) Å	0.46 × 0.24 × 0.20 mm

Data collection top

Siemens CCD area-detectorr diffractometer	5171 independent reflections
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	3106 reflections with I > 2σ(I)
T_min = 0.534, T_max = 0.746	R_int = 0.082
27642 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	69 restraints
wR(F²) = 0.144	H-atom parameters constrained
S = 0.96	Δρ_max = 0.39 e Å⁻³
5171 reflections	Δρ_min = −0.50 e Å⁻³
199 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Zn1	0.01584 (3)	0.46435 (3)	0.42416 (2)	0.0603 (2)
S1	0.06436 (7)	0.28027 (7)	0.41416 (3)	0.0684 (3)
S2	−0.02709 (7)	0.41446 (8)	0.32706 (4)	0.0691 (3)
S3	0.08445 (8)	0.63874 (8)	0.41903 (4)	0.0768 (3)
S4	0.12047 (6)	0.50962 (7)	0.52327 (4)	0.0597 (2)
N1	0.0193 (2)	0.2026 (2)	0.3131 (1)	0.074 (1)
N2	0.1683 (2)	0.7232 (2)	0.5078 (1)	0.061 (1)
C1	0.0190 (2)	0.2898 (3)	0.3471 (1)	0.060 (1)
C2	−0.0195 (4)	0.2080 (4)	0.2550 (2)	0.103 (2)
C3	−0.1165 (4)	0.1744 (5)	0.2539 (2)	0.151 (2)
C4	0.0569 (4)	0.0942 (3)	0.3296 (2)	0.101 (1)	0.50
C5	0.1509 (9)	0.070 (1)	0.310 (1)	0.115 (3)	0.50
C6	0.168 (1)	−0.053 (1)	0.3195 (5)	0.138 (4)	0.50
C7	0.267 (1)	−0.071 (2)	0.3213 (7)	0.173 (5)	0.50
C4'	0.0569 (4)	0.0942 (3)	0.3296 (2)	0.101 (1)	0.50
C5'	0.1567 (7)	0.085 (1)	0.318 (1)	0.115 (3)	0.50
C6'	0.192 (1)	−0.023 (1)	0.3411 (5)	0.138 (4)	0.50
C7'	0.237 (1)	−0.094 (2)	0.3000 (6)	0.173 (5)	0.50
C8	0.1277 (2)	0.6343 (2)	0.4863 (1)	0.055 (1)
C9	0.1764 (3)	0.8286 (3)	0.4762 (2)	0.080 (1)
C10	0.0965 (3)	0.9051 (4)	0.4865 (2)	0.107 (2)
C11	0.2067 (2)	0.7240 (3)	0.5651 (1)	0.072 (1)
C12	0.3068 (3)	0.6979 (5)	0.5652 (2)	0.099 (1)
C13	0.3476 (4)	0.7050 (7)	0.6232 (2)	0.173 (3)
C14	0.3247 (7)	0.6064 (8)	0.6557 (3)	0.262 (6)
H2a	−0.0139	0.2833	0.2408	0.123*
H2b	0.0150	0.1594	0.2305	0.123*
H3a	−0.1390	0.1789	0.2161	0.226*
H3b	−0.1511	0.2232	0.2776	0.226*
H3C	−0.1222	0.0994	0.2673	0.226*
H4a	0.0168	0.0365	0.3156	0.121*	0.50
H4b	0.0564	0.0896	0.3703	0.121*	0.50
H5a	0.1947	0.1141	0.3301	0.139*	0.50
H5b	0.1565	0.0868	0.2699	0.139*	0.50
H6a	0.1409	−0.0759	0.3548	0.165*	0.50
H6b	0.1414	−0.0966	0.2895	0.165*	0.50
H7a	0.2794	−0.1486	0.3276	0.260*	0.50
H7b	0.2930	−0.0282	0.3514	0.260*	0.50
H7c	0.2936	−0.0485	0.2863	0.260*	0.50
H4'1	0.0250	0.0359	0.3094	0.121*	0.50
H4'2	0.0466	0.0828	0.3694	0.121*	0.50
H5'1	0.1672	0.0873	0.2774	0.139*	0.50
H5'2	0.1887	0.1467	0.3347	0.139*	0.50
H6'1	0.2343	−0.0063	0.3710	0.165*	0.50
H6'2	0.1413	−0.0633	0.3574	0.165*	0.50
H7'1	0.2570	−0.1607	0.3180	0.260*	0.50
H7'2	0.2877	−0.0553	0.2842	0.260*	0.50
H7'3	0.1946	−0.1125	0.2706	0.260*	0.50
H9a	0.1803	0.8122	0.4363	0.096*
H9b	0.2319	0.8661	0.4872	0.096*
H10a	0.1043	0.9723	0.4653	0.161*
H10b	0.0931	0.9226	0.5258	0.161*
H10c	0.0415	0.8688	0.4750	0.161*
H11a	0.1750	0.6697	0.5880	0.086*
H11b	0.1971	0.7967	0.5818	0.086*
H12a	0.3160	0.6235	0.5505	0.119*
H12b	0.3380	0.7496	0.5406	0.119*
H13a	0.4130	0.7117	0.6203	0.207*
H13b	0.3247	0.7706	0.6422	0.207*
H14a	0.3511	0.6120	0.6925	0.393*
H14b	0.3481	0.5416	0.6371	0.393*
H14c	0.2599	0.6005	0.6590	0.393*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0644 (3)	0.0519 (3)	0.0644 (3)	−0.0003 (2)	0.0004 (2)	−0.0111 (2)
S1	0.0812 (6)	0.0612 (5)	0.0629 (5)	0.0155 (4)	−0.0111 (4)	−0.0080 (4)
S2	0.0868 (6)	0.0580 (5)	0.0624 (5)	0.0064 (4)	−0.0145 (4)	−0.0073 (4)
S3	0.0958 (7)	0.0708 (6)	0.0637 (5)	−0.0241 (5)	−0.0127 (5)	0.0003 (4)
S4	0.0559 (5)	0.0495 (4)	0.0736 (5)	0.0071 (3)	−0.0023 (4)	−0.0065 (3)
N1	0.095 (2)	0.057 (2)	0.070 (2)	0.005 (2)	−0.008 (2)	−0.015 (1)
N2	0.056 (2)	0.057 (2)	0.071 (2)	−0.008 (1)	−0.010 (1)	−0.005 (1)
C1	0.063 (2)	0.051 (2)	0.066 (2)	−0.001 (1)	0.000 (2)	−0.011 (2)
C2	0.149 (5)	0.079 (3)	0.079 (3)	0.020 (3)	−0.025 (3)	−0.030 (2)
C3	0.162 (6)	0.128 (5)	0.161 (5)	−0.036 (4)	−0.058 (4)	−0.014 (4)
C4	0.154 (5)	0.050 (2)	0.097 (3)	0.012 (2)	−0.005 (3)	−0.014 (2)
C5	0.143 (5)	0.091 (5)	0.112 (7)	0.048 (4)	0.010 (4)	0.000 (5)
C6	0.194 (9)	0.142 (9)	0.076 (8)	0.075 (8)	0.002 (6)	−0.006 (6)
C7	0.20 (1)	0.148 (9)	0.17 (1)	0.073 (9)	−0.089 (8)	−0.026 (7)
C4'	0.154 (5)	0.050 (2)	0.097 (3)	0.012 (2)	−0.005 (3)	−0.014 (2)
C5'	0.143 (5)	0.091 (5)	0.112 (7)	0.048 (4)	0.010 (4)	0.000 (5)
C6'	0.194 (9)	0.142 (9)	0.076 (8)	0.075 (8)	0.002 (6)	−0.006 (6)
C7'	0.20 (1)	0.148 (9)	0.17 (1)	0.073 (9)	−0.089 (8)	−0.026 (7)
C8	0.045 (2)	0.055 (2)	0.066 (2)	0.002 (1)	0.002 (1)	−0.007 (1)
C9	0.089 (3)	0.061 (2)	0.090 (3)	−0.024 (2)	−0.017 (2)	0.004 (2)
C10	0.141 (4)	0.060 (3)	0.121 (4)	0.012 (3)	−0.006 (3)	0.007 (2)
C11	0.072 (2)	0.070 (2)	0.074 (2)	−0.00 (2)	−0.016 (2)	−0.009 (2)
C12	0.067 (3)	0.124 (4)	0.107 (3)	−0.011 (2)	−0.020 (2)	0.008 (3)
C13	0.099 (4)	0.277 (9)	0.142 (5)	−0.027 (5)	−0.037 (4)	0.090 (6)
C14	0.21 (1)	0.41 (2)	0.170 (8)	0.00 (1)	−0.056 (7)	0.067 (9)

Geometric parameters (Å, º) top

Zn1—S1	2.338 (1)	C4—H4a	0.9700
Zn1—S2	2.470 (1)	C4—H4b	0.9700
Zn1—S3	2.331 (1)	C5—H5a	0.9700
Zn1—S4	2.870 (1)	C5—H5b	0.9700
Zn1—S4ⁱ	2.386 (1)	C6—H6a	0.9700
S1—C1	1.735 (3)	C6—H6b	0.9700
S2—C1	1.713 (3)	C7—H7a	0.9600
S3—C8	1.723 (3)	C7—H7b	0.9600
S4—C8	1.742 (3)	C7—H7C	0.9600
N1—C1	1.324 (4)	C5'—H5'1	0.9700
N1—C4	1.470 (5)	C5'—H5'2	0.9700
N1—C2	1.497 (5)	C6'—H6'1	0.9700
N2—C8	1.327 (4)	C6'—H6'2	0.9700
N2—C11	1.477 (4)	C7'—H7'1	0.9600
N2—C9	1.479 (4)	C7'—H7'2	0.9600
C2—C3	1.485 (6)	C7'—H7'3	0.9600
C4—C5	1.494 (7)	C9—H9a	0.9700
C5—C6	1.515 (8)	C9—H9b	0.9700
C6—C7	1.475 (8)	C10—H10a	0.9600
C5'—C6'	1.500 (8)	C10—H10b	0.9600
C6'—C7'	1.458 (8)	C10—H10c	0.9600
C9—C10	1.514 (6)	C11—H11a	0.9700
C11—C12	1.509 (5)	C11—H11b	0.9700
C12—C13	1.508 (5)	C12—H12a	0.9700
C13—C14	1.455 (7)	C12—H12b	0.9700
C2—H2a	0.9700	C13—H13a	0.9700
C2—H2b	0.9700	C13—H13b	0.9700
C3—H3a	0.9600	C14—H14a	0.9600
C3—H3b	0.9600	C14—H14b	0.9600
C3—H3C	0.9600	C14—H14c	0.9600

S1—Zn1—S2	75.7 (1)	C7—C6—H6a	110.0
S1—Zn1—S3	135.6 (1)	C5—C6—H6a	110.0
S1—Zn1—S4	95.7 (1)	C7—C6—H6b	110.0
S1—Zn1—S4ⁱ	115.8 (1)	C5—C6—H6b	110.0
S2—Zn1—S3	106.3 (1)	H6a—C6—H6b	108.4
S2—Zn1—S4	162.3 (1)	C6—C7—H7a	109.5
S2—Zn1—S4ⁱ	107.9 (1)	C6—C7—H7b	109.5
S3—Zn1—S4	68.9 (1)	H7a—C7—H7b	109.5
S3—Zn1—S4ⁱ	105.9 (1)	C6—C7—H7c	109.5
S4—Zn1—S4ⁱ	89.8 (1)	H7a—C7—H7c	109.5
C1—S1—Zn1	85.0 (1)	H7b—C7—H7c	109.5
C1—S2—Zn1	81.4 (1)	C6'—C5'—H5'1	109.8
C8—S3—Zn1	94.8 (1)	C6'—C5'—H5'2	109.8
C8—S4—Zn1ⁱ	101.8 (1)	H5'1—C5'—H5'2	108.3
C8—S4—Zn1	77.3 (1)	C7'—C6'—H6'1	108.7
Zn1—S4—Zn1ⁱ	90.2 (1)	C5'—C6'—H6'1	108.7
C1—N1—C4	122.7 (3)	C7'—C6'—H6'2	108.7
C1—N1—C2	121.9 (3)	C5'—C6'—H6'2	108.7
C4—N1—C2	115.3 (3)	H6'1—C6'—H6'2	107.6
C8—N2—C11	122.3 (3)	C6'—C7'—H7'1	109.5
C8—N2—C9	122.0 (3)	C6'—C7'—H7'2	109.5
C11—N2—C9	115.7 (3)	H7'1—C7'—H7'2	109.5
N1—C1—S2	121.6 (3)	C6'—C7'—H7'3	109.5
N1—C1—S1	120.6 (3)	H7'1—C7'—H7'3	109.5
S2—C1—S1	117.8 (2)	H7'2—C7'—H7'3	109.5
C3—C2—N1	111.8 (4)	N2—C9—H9a	109.2
N1—C4—C5	116.1 (7)	C10—C9—H9a	109.2
C4—C5—C6	107.3 (8)	N2—C9—H9b	109.2
C7—C6—C5	108 (1)	C10—C9—H9b	109.2
C7'—C6'—C5'	114 (1)	H9a—C9—H9b	107.9
N2—C8—S3	120.0 (2)	C9—C10—H10a	109.5
N2—C8—S4	121.7 (2)	C9—C10—H10b	109.5
S3—C8—S4	118.2 (2)	H10a—C10—H10b	109.5
N2—C9—C10	112.0 (3)	C9—C10—H10c	109.5
N2—C11—C12	112.0 (3)	H10a—C10—H10c	109.5
C13—C12—C11	112.2 (4)	H10b—C10—H10c	109.5
C14—C13—C12	110.3 (6)	N2—C11—H11a	109.2
C3—C2—H2a	109.2	C12—C11—H11a	109.2
N1—C2—H2a	109.2	N2—C11—H11b	109.2
C3—C2—H2b	109.2	C12—C11—H11b	109.2
N1—C2—H2b	109.2	H11a—C11—H11b	107.9
H2a—C2—H2b	107.9	C13—C12—H12a	109.2
C2—C3—H3a	109.5	C11—C12—H12a	109.2
C2—C3—H3b	109.5	C13—C12—H12b	109.2
H3a—C3—H3b	109.5	C11—C12—H12b	109.2
C2—C3—H3c	109.5	H12a—C12—H12b	107.9
H3a—C3—H3c	109.5	C14—C13—H13a	109.6
H3b—C3—H3c	109.5	C12—C13—H13a	109.6
N1—C4—H4a	108.3	C14—C13—H13b	109.6
C5—C4—H4a	108.3	C12—C13—H13b	109.6
N1—C4—H4b	108.3	H13a—C13—H13b	108.1
C5—C4—H4b	108.3	C13—C14—H14a	109.5
H4a—C4—H4b	107.4	C13—C14—H14b	109.5
C4—C5—H5a	110.3	H14a—C14—H14b	109.5
C6—C5—H5a	110.3	C13—C14—H14c	109.5
C4—C5—H5b	110.3	H14a—C14—H14c	109.5
C6—C5—H5b	110.3	H14b—C14—H14c	109.5
H5a—C5—H5b	108.5

S3—Zn1—S1—C1	−100.0 (1)	Zn1—S2—C1—S1	−1.8 (2)
S4ⁱ—Zn1—S1—C1	102.0 (1)	Zn1—S1—C1—N1	−177.3 (3)
S2—Zn1—S1—C1	−1.2 (1)	Zn1—S1—C1—S2	1.9 (2)
S4—Zn1—S1—C1	−165.5 (1)	C1—N1—C2—C3	−91.9 (5)
S3—Zn1—S2—C1	135.1 (1)	C4—N1—C2—C3	87.7 (5)
S1—Zn1—S2—C1	1.2 (1)	C1—N1—C4—C5	−99 (2)
S4ⁱ—Zn1—S2—C1	−111.7 (1)	C2—N1—C4—C5	82 (2)
S4—Zn1—S2—C1	63.7 (2)	N1—C4—C5—C6	−167 (1)
S1—Zn1—S3—C8	−81.1 (1)	C4—C5—C6—C7	−158 (2)
S4ⁱ—Zn1—S3—C8	78.3 (1)	C11—N2—C8—S3	−179.9 (2)
S2—Zn1—S3—C8	−167.1 (1)	C9—N2—C8—S3	1.2 (4)
S4—Zn1—S3—C8	−5.1 (1)	C11—N2—C8—S4	−2.4 (4)
S3—Zn1—S4—C8	5.2 (1)	C9—N2—C8—S4	178.7 (2)
S1—Zn1—S4—C8	142.1 (1)	Zn1—S3—C8—N2	−173.5 (2)
S4ⁱ—Zn1—S4—C8	−102.0 (1)	Zn1—S3—C8—S4	9.0 (2)
S2—Zn1—S4—C8	82.4 (1)	Zn1ⁱ—S4—C8—N2	87.5 (3)
S3—Zn1—S4—Zn1ⁱ	107.2 (1)	Zn1—S4—C8—N2	175.0 (3)
S1—Zn1—S4—Zn1ⁱ	−115.9 (1)	Zn1ⁱ—S4—C8—S3	−95.0 (2)
S4ⁱ—Zn1—S4—Zn1ⁱ	0.0 (1)	Zn1—S4—C8—S3	−7.5 (1)
S2—Zn1—S4—Zn1ⁱ	−175.6 (1)	C8—N2—C9—C10	90.3 (4)
C4—N1—C1—S2	−178.9 (3)	C11—N2—C9—C10	−88.7 (4)
C2—N1—C1—S2	0.7 (5)	C8—N2—C11—C12	95.3 (4)
C4—N1—C1—S1	0.2 (5)	C9—N2—C11—C12	−85.7 (4)
C2—N1—C1—S1	179.9 (3)	N2—C11—C12—C13	176.7 (4)
Zn1—S2—C1—N1	177.4 (3)	C11—C12—C13—C14	77.5 (8)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2a···S2	0.97	2.60	3.019 (5)	107
C4—H4b···S1	0.97	2.52	3.011 (4)	111
C9—H9a···S3	0.97	2.55	2.983 (4)	107
C11—H11a···S4	0.97	2.59	3.041 (3)	108

Experimental details

Crystal data
Chemical formula	[Zn₂(C₇H₁₄NS₂)₄]
M_r	835.99
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	14.7301 (2), 12.0254 (2), 23.7960 (1)
V (Å³)	4215.11 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.56
Crystal size (mm)	0.46 × 0.24 × 0.20

Data collection
Diffractometer	Siemens CCD area-detectorr diffractometer
Absorption correction	Empirical (using intensity measurements) (SADABS; Sheldrick, 1996)
T_min, T_max	0.534, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	27642, 5171, 3106
R_int	0.082
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.144, 0.96
No. of reflections	5171
No. of parameters	199
No. of restraints	69
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.50

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97.

Selected geometric parameters (Å, º) top

Zn1—S1	2.338 (1)	Zn1—S4	2.870 (1)
Zn1—S2	2.470 (1)	Zn1—S4ⁱ	2.386 (1)
Zn1—S3	2.331 (1)

S1—Zn1—S2	75.7 (1)	S2—Zn1—S4ⁱ	107.9 (1)
S1—Zn1—S3	135.6 (1)	S3—Zn1—S4	68.9 (1)
S1—Zn1—S4	95.7 (1)	S3—Zn1—S4ⁱ	105.9 (1)
S1—Zn1—S4ⁱ	115.8 (1)	S4—Zn1—S4ⁱ	89.8 (1)
S2—Zn1—S3	106.3 (1)	Zn1—S4—Zn1ⁱ	90.2 (1)
S2—Zn1—S4	162.3 (1)

Symmetry code: (i) −x, −y+1, −z+1.

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