Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536800020808/na6028sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536800020808/na6028Isup2.hkl |
CCDC reference: 159702
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
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.
One of the two butyl chains is disordered in two positions; the chain was refined as two chains sharing a commond C1 atom. The occupancy was fixed at 0.5 as it refined to approximately 0.5. Pairs of 1,2- and 1,3-related C atoms were restrained by SADI 0.01 and SADI 0.02 instructions for the ordered and disordered butyl chains. The unprimed and primed atoms were restrained to have the same displacement parameters; additionally, an ISOR 0.02 command was imposed on the disordered atoms.
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.
Fig. 1. ORTEPII (Johnson, 1976) plot of the title compound at the 50% probability level. H atoms are shown as circles of arbitrary radii. |
[Zn2(C7H14NS2)4] | Dx = 1.317 Mg m−3 |
Mr = 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 |
Siemens CCD area-detectorr diffractometer | 5171 independent reflections |
Radiation source: fine-focus sealed tube | 3106 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.082 |
Detector resolution: 8.33 pixels mm-1 | θmax = 28.2°, θmin = 1.7° |
ω scans | h = −17→19 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = −14→15 |
Tmin = 0.534, Tmax = 0.746 | l = −30→31 |
27642 measured reflections |
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(Fo2) + (0.0802P)2] where P = (Fo2 + 2Fc2)/3 |
5171 reflections | (Δ/σ)max = 0.001 |
199 parameters | Δρmax = 0.39 e Å−3 |
69 restraints | Δρmin = −0.50 e Å−3 |
[Zn2(C7H14NS2)4] | V = 4215.11 (9) Å3 |
Mr = 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 |
Siemens CCD area-detectorr diffractometer | 5171 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | 3106 reflections with I > 2σ(I) |
Tmin = 0.534, Tmax = 0.746 | Rint = 0.082 |
27642 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 69 restraints |
wR(F2) = 0.144 | H-atom parameters constrained |
S = 0.96 | Δρmax = 0.39 e Å−3 |
5171 reflections | Δρmin = −0.50 e Å−3 |
199 parameters |
x | y | z | Uiso*/Ueq | 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* |
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) |
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. |
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] |
Mr | 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) |
Tmin, Tmax | 0.534, 0.746 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 27642, 5171, 3106 |
Rint | 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 |
Δρmax, Δρmin (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.
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. |
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).