Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 2| February 2010| Page m215
https://doi.org/10.1107/S1600536810002825

Bis(N-iso­butyl-N-propyl­di­thio­carbamato-κ2S,S′)zinc(II)

Norma Awang,a Ibrahim Baba,a Bohari M. Yamina and Seik Weng Ngb*

aSchool of Chemical Sciences, Universiti Kebangbaan Malaysia, 43600 Bangi, Malaysia, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 19 January 2010; accepted 22 January 2010; online 30 January 2010)

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[Chan, M. Y., Lai, C. S. & Tiekink, E. R. T. (2004). Appl. Organomet. Chem. 18, 298.]); Cox & Tiekink (1999[Cox, M. J. & Tiekink, E. R. T. (1999). Z. Kristallogr. 214, 184-190.]); Decken et al. (2004[Decken, A., Gossage, R. A., Chan, M. Y., Lai, C. S. & Tiekink, E. R. T. (2004). Appl. Organomet. Chem. 18, 101-102.]); Reck & Becker (2003[Reck, G. & Becker, R. (2003). Acta Cryst. E59, m234-m235.]); Zhong et al. (2003[Zhong, Y., Zhang, W.-G., Zhang, Q.-J., Tan, M.-Y. & Weng, S.-L. (2003). Acta Chim. Sin. 61, 1828-1833.]).

[Scheme 1]

Experimental

Crystal data

  • [Zn(C8H16NS2)2]

  • Mr = 446.05

  • Monoclinic, P 21 /n

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.673, Tmax = 0.716

  • 15340 measured reflections

  • 5279 independent reflections

  • 3971 reflections with I > 2σ(I)

  • Rint = 0.020
Refinement

  • R[F2 > 2σ(F2)] = 0.052

  • wR(F2) = 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

Table 1
Selected geometric parameters (Å, °)

Zn1—S4 2.3256 (11)
Zn1—S1 2.3375 (11)
Zn1—S2 2.3434 (10)
Zn1—S3 2.3560 (10)
S4—Zn1—S1 130.64 (5)
S4—Zn1—S2 129.21 (5)
S1—Zn1—S2 77.59 (4)
S4—Zn1—S3 77.52 (3)
S1—Zn1—S3 126.46 (5)
S2—Zn1—S3 123.05 (5)

Data collection: SMART (Bruker, 2000[Bruker (2000). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). publCIF. In preparation.]).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810002825/hb5312Isup2.hkl

checkCIF report


Related literature top

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

Experimental top

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 top

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).

Structure description top

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

Computing details top

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

Figures top
[Figure 1] Fig. 1. View of (I) at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder is not shown.
Bis(N-isobutyl-N-propyldithiocarbamato- κ2S,S')zinc(II) top
Crystal data top
[Zn(C8H16NS2)2]F(000) = 944
Mr = 446.05Dx = 1.289 Mg m−3
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 mm−1
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 top
Bruker SMART APEX
diffractometer		5279 independent reflections
Radiation source: fine-focus sealed tube3971 reflections with I > 2σ(I)
Graphite monochromatorRint = 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 top
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 = 1.03 w = 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 Å−3
80 restraintsΔρmin = −0.48 e Å−3
Crystal data top
[Zn(C8H16NS2)2]V = 2299.15 (19) Å3
Mr = 446.05Z = 4
Monoclinic, P21/nMo Kα radiation
a = 14.2151 (7) ŵ = 1.43 mm−1
b = 11.8527 (6) ÅT = 293 K
c = 15.1428 (7) Å0.30 × 0.30 × 0.25 mm
β = 115.691 (1)°
Data collection top
Bruker SMART APEX
diffractometer		5279 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3971 reflections with I > 2σ(I)
Tmin = 0.673, Tmax = 0.716Rint = 0.020
15340 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05280 restraints
wR(F2) = 0.166H-atom parameters constrained
S = 1.03Δρmax = 0.93 e Å−3
5279 reflectionsΔρmin = −0.48 e Å−3
250 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, º) top
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)

Experimental details

Crystal data
Chemical formula[Zn(C8H16NS2)2]
Mr446.05
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)14.2151 (7), 11.8527 (6), 15.1428 (7)
β (°) 115.691 (1)
V (Å3)2299.15 (19)
Z4
Radiation typeMo Kα
µ (mm−1)1.43
Crystal size (mm)0.30 × 0.30 × 0.25
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.673, 0.716
No. of measured, independent and
observed [I > 2σ(I)] reflections		15340, 5279, 3971
Rint0.020
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.166, 1.03
No. of reflections5279
No. of parameters250
No. of restraints80
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.93, −0.48

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Selected geometric parameters (Å, º) top
Zn1—S42.3256 (11)Zn1—S22.3434 (10)
Zn1—S12.3375 (11)Zn1—S32.3560 (10)
S4—Zn1—S1130.64 (5)S4—Zn1—S377.52 (3)
S4—Zn1—S2129.21 (5)S1—Zn1—S3126.46 (5)
S1—Zn1—S277.59 (4)S2—Zn1—S3123.05 (5)
 

Acknowledgements

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.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
 First citationBruker (2000). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationChan, M. Y., Lai, C. S. & Tiekink, E. R. T. (2004). Appl. Organomet. Chem. 18, 298.  Web of Science CSD CrossRef Google Scholar
 First citationCox, M. J. & Tiekink, E. R. T. (1999). Z. Kristallogr. 214, 184–190.  Web of Science CSD CrossRef CAS Google Scholar
 First citationDecken, A., Gossage, R. A., Chan, M. Y., Lai, C. S. & Tiekink, E. R. T. (2004). Appl. Organomet. Chem. 18, 101–102.  Web of Science CSD CrossRef CAS Google Scholar
 First citationReck, G. & Becker, R. (2003). Acta Cryst. E59, m234–m235.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWestrip, S. P. (2010). publCIF. In preparation.  Google Scholar
 First citationZhong, Y., Zhang, W.-G., Zhang, Q.-J., Tan, M.-Y. & Weng, S.-L. (2003). Acta Chim. Sin. 61, 1828–1833.  CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 2| February 2010| Page m215
https://doi.org/10.1107/S1600536810002825
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS