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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): m215.
Published online 2010 January 30. doi:  10.1107/S1600536810002825
PMCID: PMC2979964

Bis(N-isobutyl-N-propyl­dithio­carbamato-κ2 S,S′)zinc(II)

Abstract

In the title compound, [Zn(C8H16NS2)2], the ZnII atom is chelated by two S,S′-bidentate dithio­carbamate ions in a very distorted tetra­hedral geometry. The alkyl chains of the ligands are equally disordered over two sets of sites.

Related literature

For other monomeric zinc bis­(dithio­carbamates), see: Chan et al. (2004 [triangle]); Cox & Tiekink (1999 [triangle]); Decken et al. (2004 [triangle]); Reck & Becker (2003 [triangle]); Zhong et al. (2003 [triangle]).

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Object name is e-66-0m215-scheme1.jpg

Experimental

Crystal data

  • [Zn(C8H16NS2)2]
  • M r = 446.05
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m215-efi1.jpg
  • a = 14.2151 (7) Å
  • b = 11.8527 (6) Å
  • c = 15.1428 (7) Å
  • β = 115.691 (1)°
  • V = 2299.15 (19) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.43 mm−1
  • T = 293 K
  • 0.30 × 0.30 × 0.25 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.673, T max = 0.716
  • 15340 measured reflections
  • 5279 independent reflections
  • 3971 reflections with I > 2σ(I)
  • R int = 0.020

Refinement

  • R[F 2 > 2σ(F 2)] = 0.052
  • wR(F 2) = 0.166
  • S = 1.03
  • 5279 reflections
  • 250 parameters
  • 80 restraints
  • H-atom parameters constrained
  • Δρmax = 0.93 e Å−3
  • Δρmin = −0.48 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Selected geometric parameters (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810002825/hb5312sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002825/hb5312Isup2.hkl

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

Acknowledgments

We thank Universiti Kebangsaan Malaysia (UKM-GUP-NBT-08-27-111 and 06-01-02-SF0539) and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

Zinc chloride (10 mmol), i-butyl-n-propylamine (20 mmol), carbon disulfide (20 mmol) and ammonia (10 ml) were reacted in ethanol (30 ml) at 277 K to produce a white solid. This was collected and recrystallized from ethanol to yield colourless blocks of (I).

Refinement

The carbon atoms of the alkyl chains (except for the four atoms connected to the nitrogen atoms) show large displacement ellipsoids. The disorder could not be refined, and was assumed to be a 1:1 disorder. The 1,2-related carbon-carbon distances were restrained to 1.50±0.01 Å and the 1,3-related ones to 2.35±0.01 Å. The temperature factors of the primed atoms were set to those of the unprimed ones; the anisotropic temperature factors of all disordered atoms were restrained to be nearly isotropic.

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93 to 0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C).

Figures

Fig. 1.
View of (I) at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder is not shown.

Crystal data

[Zn(C8H16NS2)2]F(000) = 944
Mr = 446.05Dx = 1.289 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4652 reflections
a = 14.2151 (7) Åθ = 2.3–26.4°
b = 11.8527 (6) ŵ = 1.43 mm1
c = 15.1428 (7) ÅT = 293 K
β = 115.691 (1)°Block, colourless
V = 2299.15 (19) Å30.30 × 0.30 × 0.25 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer5279 independent reflections
Radiation source: fine-focus sealed tube3971 reflections with I > 2σ(I)
graphiteRint = 0.020
ω scansθmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −18→9
Tmin = 0.673, Tmax = 0.716k = −15→15
15340 measured reflectionsl = −18→19

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0943P)2 + 1.1606P] where P = (Fo2 + 2Fc2)/3
5279 reflections(Δ/σ)max = 0.001
250 parametersΔρmax = 0.93 e Å3
80 restraintsΔρmin = −0.48 e Å3

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

xyzUiso*/UeqOcc. (<1)
Zn10.55521 (3)0.44936 (4)0.32988 (4)0.06385 (19)
S10.62441 (7)0.27447 (8)0.31726 (9)0.0732 (3)
S20.73544 (7)0.48158 (9)0.41144 (10)0.0779 (3)
S30.44152 (8)0.56222 (9)0.19904 (8)0.0685 (3)
S40.42531 (7)0.49493 (10)0.37820 (7)0.0669 (3)
N10.8309 (2)0.2955 (3)0.3903 (3)0.0709 (9)
N20.2993 (2)0.6465 (3)0.2508 (2)0.0671 (8)
C10.7415 (3)0.3442 (3)0.3754 (3)0.0580 (8)
C20.8334 (3)0.1754 (3)0.3595 (4)0.0752 (11)
H2A0.77170.16020.29910.090*0.50
H2B0.89420.16400.34710.090*0.50
H2C0.77970.16630.29300.090*0.50
H2D0.90020.16210.35830.090*0.50
C50.9327 (3)0.3572 (4)0.4397 (4)0.0952 (17)
H5A0.91470.43550.44640.114*0.50
H5B0.91900.43490.45300.114*0.50
C90.3786 (2)0.5769 (3)0.2728 (2)0.0530 (7)
C100.2641 (3)0.7191 (4)0.1610 (3)0.0760 (12)
H10A0.32580.74840.15690.091*0.50
H10B0.22660.78310.17000.091*0.50
H10C0.32390.73990.14950.091*0.50
H10D0.23280.78770.17100.091*0.50
C130.2460 (4)0.6573 (5)0.3161 (4)0.1049 (19)
H13A0.28540.61050.37380.126*0.50
H13B0.27050.59730.36550.126*0.50
C30.837 (2)0.095 (2)0.4378 (17)0.077 (3)0.50
H3A0.77260.09960.44500.092*0.50
H3B0.89450.11460.50000.092*0.50
C40.852 (5)−0.0219 (13)0.408 (4)0.096 (4)0.50
H4A0.8554−0.07460.45760.144*0.50
H4B0.9151−0.02520.40020.144*0.50
H4C0.7937−0.04090.34700.144*0.50
C61.0024 (12)0.362 (3)0.3931 (11)0.123 (3)0.50
H6A1.04370.29390.40670.148*0.50
H6B1.04960.42580.41860.148*0.50
C70.9398 (14)0.3752 (14)0.2859 (9)0.105 (3)0.50
H7A0.98440.36690.25350.157*0.50
H7B0.90820.44860.27220.157*0.50
H7C0.88640.31840.26270.157*0.50
C81.002 (2)0.315 (4)0.5456 (14)0.119 (4)0.50
H8A0.97520.34460.58940.179*0.50
H8B1.07220.34030.56580.179*0.50
H8C1.00040.23400.54690.179*0.50
C110.196 (2)0.6651 (19)0.0648 (10)0.072 (5)0.50
H11A0.13160.63900.06500.086*0.50
H11B0.23170.60100.05320.086*0.50
C120.174 (4)0.752 (3)−0.0135 (9)0.107 (4)0.50
H12A0.12810.7209−0.07590.160*0.50
H12B0.23800.7750−0.01480.160*0.50
H12C0.14120.81650.00010.160*0.50
C140.2359 (12)0.7698 (14)0.353 (2)0.129 (4)0.50
H14A0.20990.76300.40260.155*0.50
H14B0.18820.81670.30030.155*0.50
C150.3433 (17)0.8197 (16)0.3967 (19)0.159 (14)0.50
H15A0.34110.89390.42110.239*0.50
H15B0.36840.82430.34730.239*0.50
H15C0.38930.77290.44950.239*0.50
C160.1365 (9)0.6086 (15)0.268 (2)0.137 (5)0.50
H16A0.13880.52970.28290.206*0.50
H16B0.10860.61820.19800.206*0.50
H16C0.09270.64710.29170.206*0.50
C3'0.818 (2)0.087 (2)0.4221 (18)0.077 (3)0.50
H3'A0.74520.08580.41150.092*0.50
H3'B0.86090.10270.49080.092*0.50
C4'0.847 (5)−0.0254 (13)0.395 (4)0.096 (4)0.50
H4'A0.8375−0.08320.43530.144*0.50
H4'B0.9183−0.02370.40600.144*0.50
H4'C0.8028−0.04100.32750.144*0.50
C6'0.9843 (14)0.359 (3)0.3750 (12)0.123 (3)0.50
H6'A0.99500.28250.35860.148*0.50
H6'B1.05190.39510.40780.148*0.50
C7'0.9189 (15)0.4218 (13)0.2844 (9)0.105 (3)0.50
H7'A0.95720.43270.24620.157*0.50
H7'B0.90050.49390.30140.157*0.50
H7'C0.85650.37960.24700.157*0.50
C8'1.010 (2)0.303 (4)0.5354 (15)0.119 (4)0.50
H8'A1.05950.25790.52280.179*0.50
H8'B0.97350.25570.56140.179*0.50
H8'C1.04710.36070.58200.179*0.50
C11'0.185 (3)0.656 (3)0.0723 (14)0.099 (9)0.50
H11C0.21390.58470.06400.119*0.50
H11D0.12210.64070.08030.119*0.50
C12'0.161 (4)0.731 (3)−0.0147 (9)0.107 (4)0.50
H12D0.11630.6919−0.07340.160*0.50
H12E0.22490.7511−0.01800.160*0.50
H12F0.12680.7981−0.00820.160*0.50
C14'0.2732 (13)0.7661 (19)0.365 (2)0.129 (4)0.50
H14C0.24120.82410.31560.155*0.50
H14D0.24160.77080.41010.155*0.50
C15'0.373 (2)0.791 (2)0.414 (2)0.199 (15)0.50
H15D0.38040.86430.44250.298*0.50
H15E0.40560.79010.36980.298*0.50
H15F0.40630.73590.46450.298*0.50
C16'0.1275 (11)0.6532 (18)0.263 (2)0.137 (5)0.50
H16D0.10130.72640.23630.206*0.50
H16E0.09960.63120.30750.206*0.50
H16F0.10690.59930.21020.206*0.50

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn10.0423 (2)0.0630 (3)0.0817 (3)0.01003 (17)0.0227 (2)0.0059 (2)
S10.0483 (5)0.0569 (5)0.1016 (8)0.0001 (4)0.0205 (5)−0.0099 (5)
S20.0443 (5)0.0598 (5)0.1181 (9)0.0049 (4)0.0245 (5)−0.0227 (6)
S30.0601 (5)0.0842 (7)0.0756 (6)0.0210 (5)0.0428 (5)0.0234 (5)
S40.0554 (5)0.0868 (7)0.0610 (5)0.0156 (5)0.0274 (4)0.0203 (5)
N10.0508 (16)0.0522 (16)0.112 (3)0.0086 (13)0.0378 (18)−0.0017 (17)
N20.0561 (16)0.085 (2)0.0686 (18)0.0238 (16)0.0346 (15)0.0199 (16)
C10.0472 (17)0.0521 (18)0.074 (2)0.0042 (14)0.0253 (16)−0.0016 (16)
C20.070 (2)0.061 (2)0.110 (3)0.0088 (19)0.053 (2)−0.006 (2)
C50.049 (2)0.066 (3)0.169 (5)0.0063 (18)0.045 (3)−0.014 (3)
C90.0409 (15)0.0626 (19)0.0573 (18)0.0045 (14)0.0231 (14)0.0057 (15)
C100.067 (2)0.076 (3)0.091 (3)0.026 (2)0.040 (2)0.024 (2)
C130.093 (3)0.144 (5)0.102 (4)0.056 (4)0.065 (3)0.027 (3)
C30.066 (8)0.062 (4)0.100 (6)0.009 (4)0.033 (6)−0.002 (4)
C40.102 (6)0.066 (3)0.121 (9)0.008 (3)0.049 (7)−0.002 (4)
C60.096 (6)0.138 (5)0.146 (7)−0.031 (5)0.063 (6)−0.049 (6)
C70.100 (6)0.123 (9)0.104 (4)0.000 (6)0.056 (4)−0.014 (5)
C80.070 (4)0.091 (8)0.160 (6)0.011 (4)0.015 (4)0.005 (6)
C110.059 (7)0.073 (8)0.081 (11)0.004 (6)0.028 (8)0.018 (7)
C120.113 (8)0.110 (10)0.092 (3)0.031 (7)0.040 (3)0.027 (4)
C140.138 (9)0.146 (7)0.131 (6)0.049 (7)0.084 (8)0.011 (5)
C150.25 (3)0.081 (9)0.24 (3)−0.047 (15)0.19 (3)−0.053 (13)
C160.083 (4)0.202 (12)0.158 (7)0.048 (6)0.082 (5)0.022 (9)
C3'0.066 (8)0.062 (4)0.100 (6)0.009 (4)0.033 (6)−0.002 (4)
C4'0.102 (6)0.066 (3)0.121 (9)0.008 (3)0.049 (7)−0.002 (4)
C6'0.096 (6)0.138 (5)0.146 (7)−0.031 (5)0.063 (6)−0.049 (6)
C7'0.100 (6)0.123 (9)0.104 (4)0.000 (6)0.056 (4)−0.014 (5)
C8'0.070 (4)0.091 (8)0.160 (6)0.011 (4)0.015 (4)0.005 (6)
C11'0.081 (15)0.137 (19)0.072 (10)0.023 (11)0.025 (9)0.027 (10)
C12'0.113 (8)0.110 (10)0.092 (3)0.031 (7)0.040 (3)0.027 (4)
C14'0.138 (9)0.146 (7)0.131 (6)0.049 (7)0.084 (8)0.011 (5)
C15'0.19 (2)0.19 (3)0.17 (2)0.03 (2)0.041 (17)−0.085 (19)
C16'0.083 (4)0.202 (12)0.158 (7)0.048 (6)0.082 (5)0.022 (9)

Geometric parameters (Å, °)

Zn1—S42.3256 (11)C7—H7C0.9600
Zn1—S12.3375 (11)C8—H8A0.9600
Zn1—S22.3434 (10)C8—H8B0.9600
Zn1—S32.3560 (10)C8—H8C0.9600
S1—C11.719 (4)C11—C121.498 (8)
S2—C11.732 (4)C11—H11A0.9700
S3—C91.717 (3)C11—H11B0.9700
S4—C91.736 (3)C12—H12A0.9600
N1—C11.323 (4)C12—H12B0.9600
N1—C51.499 (5)C12—H12C0.9600
N1—C21.504 (5)C14—C151.498 (7)
N2—C91.318 (4)C14—H14A0.9700
N2—C131.490 (5)C14—H14B0.9700
N2—C101.499 (5)C15—H15A0.9600
C2—C3'1.496 (9)C15—H15B0.9600
C2—C31.503 (9)C15—H15C0.9600
C2—H2A0.9700C16—H16A0.9600
C2—H2B0.9700C16—H16B0.9600
C2—H2C0.9700C16—H16C0.9600
C2—H2D0.9700C3'—C4'1.499 (10)
C5—C61.447 (9)C3'—H3'A0.9700
C5—C6'1.457 (9)C3'—H3'B0.9700
C5—C8'1.533 (9)C4'—H4'A0.9600
C5—C81.556 (9)C4'—H4'B0.9600
C5—H5A0.9800C4'—H4'C0.9600
C5—H5B0.9800C6'—C7'1.480 (10)
C10—C111.498 (8)C6'—H6'A0.9700
C10—C11'1.524 (19)C6'—H6'B0.9700
C10—H10A0.9700C7'—H7'A0.9600
C10—H10B0.9700C7'—H7'B0.9600
C10—H10C0.9700C7'—H7'C0.9600
C10—H10D0.9700C8'—H8'A0.9600
C13—C14'1.452 (17)C8'—H8'B0.9600
C13—C141.477 (7)C8'—H8'C0.9600
C13—C161.518 (7)C11'—C12'1.50 (2)
C13—C16'1.521 (16)C11'—H11C0.9700
C13—H13A0.9800C11'—H11D0.9700
C13—H13B0.9800C12'—H12D0.9600
C3—C41.502 (9)C12'—H12E0.9600
C3—H3A0.9700C12'—H12F0.9600
C3—H3B0.9700C14'—C15'1.32 (2)
C4—H4A0.9600C14'—H14C0.9700
C4—H4B0.9600C14'—H14D0.9700
C4—H4C0.9600C15'—H15D0.9600
C6—C71.482 (10)C15'—H15E0.9600
C6—H6A0.9700C15'—H15F0.9600
C6—H6B0.9700C16'—H16D0.9600
C7—H7A0.9600C16'—H16E0.9600
C7—H7B0.9600C16'—H16F0.9600
S4—Zn1—S1130.64 (5)H6A—C6—H6B108.3
S4—Zn1—S2129.21 (5)C6—C7—H7A109.5
S1—Zn1—S277.59 (4)C6—C7—H7B109.5
S4—Zn1—S377.52 (3)H7A—C7—H7B109.5
S1—Zn1—S3126.46 (5)C6—C7—H7C109.5
S2—Zn1—S3123.05 (5)H7A—C7—H7C109.5
C1—S1—Zn183.12 (12)H7B—C7—H7C109.5
C1—S2—Zn182.68 (12)C5—C8—H8A109.5
C9—S3—Zn182.61 (12)C5—C8—H8B109.5
C9—S4—Zn183.14 (11)H8A—C8—H8B109.5
C1—N1—C5121.4 (3)C5—C8—H8C109.5
C1—N1—C2120.6 (3)H8A—C8—H8C109.5
C5—N1—C2118.0 (3)H8B—C8—H8C109.5
C9—N2—C13120.7 (3)C10—C11—C12107.6 (8)
C9—N2—C10120.1 (3)C10—C11—H11A110.2
C13—N2—C10119.2 (3)C12—C11—H11A110.2
N1—C1—S1121.5 (3)C10—C11—H11B110.2
N1—C1—S2122.1 (3)C12—C11—H11B110.2
S1—C1—S2116.37 (19)H11A—C11—H11B108.5
C3'—C2—N1116.0 (13)C11—C12—H12A109.5
C3—C2—N1110.6 (13)C11—C12—H12B109.5
C3—C2—H2A109.5H12A—C12—H12B109.5
N1—C2—H2A109.5C11—C12—H12C109.5
C3'—C2—H2B114.5H12A—C12—H12C109.5
C3—C2—H2B109.5H12B—C12—H12C109.5
N1—C2—H2B109.5C13—C14—C15105.9 (8)
H2A—C2—H2B108.1C13—C14—H14A110.5
C3'—C2—H2C108.3C15—C14—H14A110.5
C3—C2—H2C119.5C13—C14—H14B110.5
N1—C2—H2C108.3C15—C14—H14B110.5
C3'—C2—H2D108.3H14A—C14—H14B108.7
C3—C2—H2D102.2C14—C15—H15A109.5
N1—C2—H2D108.3C14—C15—H15B109.5
H2A—C2—H2D116.5H15A—C15—H15B109.5
H2C—C2—H2D107.4C14—C15—H15C109.5
C6—C5—N1119.6 (13)H15A—C15—H15C109.5
C6'—C5—N1109.3 (13)H15B—C15—H15C109.5
C6'—C5—C8'106.0 (8)C13—C16—H16A109.5
N1—C5—C8'114.3 (18)C13—C16—H16B109.5
C6—C5—C8104.9 (8)H16A—C16—H16B109.5
C6'—C5—C8114.9 (12)C13—C16—H16C109.5
N1—C5—C8113.5 (17)H16A—C16—H16C109.5
C6—C5—H5A105.9H16B—C16—H16C109.5
C6'—C5—H5A106.5C2—C3'—C4'108.4 (9)
N1—C5—H5A105.9C2—C3'—H3'A110.0
C8'—C5—H5A114.5C4'—C3'—H3'A110.0
C8—C5—H5A105.9C2—C3'—H3'B110.0
C6—C5—H5B107.4C4'—C3'—H3'B110.0
C6'—C5—H5B109.1H3'A—C3'—H3'B108.4
N1—C5—H5B109.1C3'—C4'—H4'A109.5
C8'—C5—H5B109.1C3'—C4'—H4'B109.5
C8—C5—H5B100.5H4'A—C4'—H4'B109.5
N2—C9—S3121.9 (3)C3'—C4'—H4'C109.5
N2—C9—S4121.9 (3)H4'A—C4'—H4'C109.5
S3—C9—S4116.21 (19)H4'B—C4'—H4'C109.5
N2—C10—C11117.2 (9)C5—C6'—C7'109.5 (9)
N2—C10—C11'110.2 (12)C5—C6'—H6'A109.8
N2—C10—H10A108.0C7'—C6'—H6'A109.8
C11—C10—H10A108.0C5—C6'—H6'B109.8
C11'—C10—H10A117.5C7'—C6'—H6'B109.8
N2—C10—H10B108.0H6'A—C6'—H6'B108.2
C11—C10—H10B108.0C6'—C7'—H7'A109.5
C11'—C10—H10B105.5C6'—C7'—H7'B109.5
H10A—C10—H10B107.2H7'A—C7'—H7'B109.5
N2—C10—H10C109.6C6'—C7'—H7'C109.5
C11—C10—H10C100.3H7'A—C7'—H7'C109.5
C11'—C10—H10C109.6H7'B—C7'—H7'C109.5
H10B—C10—H10C113.8C5—C8'—H8'A109.5
N2—C10—H10D109.6C5—C8'—H8'B109.5
C11—C10—H10D111.3H8'A—C8'—H8'B109.5
C11'—C10—H10D109.6C5—C8'—H8'C109.5
H10C—C10—H10D108.1H8'A—C8'—H8'C109.5
C14'—C13—N2108.3 (12)H8'B—C8'—H8'C109.5
C14—C13—N2119.4 (12)C12'—C11'—C10106.4 (15)
C14'—C13—C16125.1 (10)C12'—C11'—H11C110.5
C14—C13—C16106.2 (7)C10—C11'—H11C110.5
N2—C13—C16110.9 (13)C12'—C11'—H11D110.5
C14'—C13—C16'106.8 (9)C10—C11'—H11D110.5
N2—C13—C16'114.1 (13)H11C—C11'—H11D108.6
C14—C13—H13A106.5C11'—C12'—H12D109.5
N2—C13—H13A106.5C11'—C12'—H12E109.5
C16—C13—H13A106.5H12D—C12'—H12E109.5
C16'—C13—H13A122.0C11'—C12'—H12F109.5
C14'—C13—H13B109.2H12D—C12'—H12F109.5
C14—C13—H13B115.2H12E—C12'—H12F109.5
N2—C13—H13B109.2C15'—C14'—C13117.8 (17)
C16'—C13—H13B109.2C15'—C14'—H14C107.9
C2—C3—C4108.0 (9)C13—C14'—H14C107.9
C2—C3—H3A110.1C15'—C14'—H14D107.9
C4—C3—H3A110.1C13—C14'—H14D107.9
C2—C3—H3B110.1H14C—C14'—H14D107.2
C4—C3—H3B110.1C14'—C15'—H15D109.5
H3A—C3—H3B108.4C14'—C15'—H15E109.5
C3—C4—H4A109.5H15D—C15'—H15E109.5
C3—C4—H4B109.5C14'—C15'—H15F109.5
H4A—C4—H4B109.5H15D—C15'—H15F109.5
C3—C4—H4C109.5H15E—C15'—H15F109.5
H4A—C4—H4C109.5C13—C16'—H16D109.5
H4B—C4—H4C109.5C13—C16'—H16E109.5
C5—C6—C7109.0 (9)H16D—C16'—H16E109.5
C5—C6—H6A109.9C13—C16'—H16F109.5
C7—C6—H6A109.9H16D—C16'—H16F109.5
C5—C6—H6B109.9H16E—C16'—H16F109.5
C7—C6—H6B109.9
S4—Zn1—S1—C1−134.68 (14)Zn1—S4—C9—N2−173.3 (3)
S2—Zn1—S1—C1−3.07 (14)Zn1—S4—C9—S36.65 (19)
S3—Zn1—S1—C1119.05 (14)C9—N2—C10—C1180.2 (17)
S4—Zn1—S2—C1135.98 (14)C13—N2—C10—C11−102.0 (17)
S1—Zn1—S2—C13.05 (14)C9—N2—C10—C11'87.6 (19)
S3—Zn1—S2—C1−122.60 (14)C13—N2—C10—C11'−94.6 (19)
S4—Zn1—S3—C94.50 (13)C9—N2—C13—C14'108.3 (12)
S1—Zn1—S3—C9136.26 (13)C10—N2—C13—C14'−69.4 (12)
S2—Zn1—S3—C9−124.42 (13)C9—N2—C13—C14125.1 (12)
S1—Zn1—S4—C9−132.20 (13)C10—N2—C13—C14−52.7 (12)
S2—Zn1—S4—C9118.25 (13)C9—N2—C13—C16−111.0 (10)
S3—Zn1—S4—C9−4.45 (13)C10—N2—C13—C1671.3 (11)
C5—N1—C1—S1179.1 (3)C9—N2—C13—C16'−132.9 (10)
C2—N1—C1—S1−2.0 (6)C10—N2—C13—C16'49.3 (11)
C5—N1—C1—S20.1 (6)C3'—C2—C3—C465 (14)
C2—N1—C1—S2179.0 (3)N1—C2—C3—C4−174 (3)
Zn1—S1—C1—N1−174.6 (4)C6'—C5—C6—C713 (12)
Zn1—S1—C1—S24.5 (2)N1—C5—C6—C738 (3)
Zn1—S2—C1—N1174.6 (4)C8'—C5—C6—C7161 (3)
Zn1—S2—C1—S1−4.5 (2)C8—C5—C6—C7167 (3)
C1—N1—C2—C3'−74.6 (14)N2—C10—C11—C12−178 (3)
C5—N1—C2—C3'104.4 (14)C11'—C10—C11—C12136 (18)
C1—N1—C2—C3−85.3 (14)C14'—C13—C14—C156(6)
C5—N1—C2—C393.7 (14)N2—C13—C14—C15−51 (3)
C1—N1—C5—C6−127.5 (15)C16—C13—C14—C15−177 (2)
C2—N1—C5—C653.5 (15)C16'—C13—C14—C15−168 (3)
C1—N1—C5—C6'−122.5 (12)C3—C2—C3'—C4'−104 (14)
C2—N1—C5—C6'58.5 (12)N1—C2—C3'—C4'−167 (3)
C1—N1—C5—C8'118.9 (15)C6—C5—C6'—C7'−140 (17)
C2—N1—C5—C8'−60.0 (15)N1—C5—C6'—C7'63 (3)
C1—N1—C5—C8107.7 (16)C8'—C5—C6'—C7'−174 (3)
C2—N1—C5—C8−71.2 (16)C8—C5—C6'—C7'−168 (3)
C13—N2—C9—S3179.9 (4)N2—C10—C11'—C12'−176 (3)
C10—N2—C9—S3−2.4 (5)C11—C10—C11'—C12'−38 (14)
C13—N2—C9—S4−0.2 (6)C14—C13—C14'—C15'176 (11)
C10—N2—C9—S4177.6 (3)N2—C13—C14'—C15'−54 (4)
Zn1—S3—C9—N2173.4 (3)C16—C13—C14'—C15'172 (3)
Zn1—S3—C9—S4−6.58 (18)C16'—C13—C14'—C15'−178 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5312).

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