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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 72| Part 3| March 2016| Pages 417-419
doi:10.1107/S2056989016002607

Crystal structure of di­chlorido­bis­­(di­methyl N-cyano­di­thio­imino­carbonate)zinc

CROSSMARK_Color_square_no_text.svg
Mouhamadou Birame Diop,a* Libasse Diopa and Allen G. Oliverb

aLaboratoire de Chimie Minérale et Analytique, Département de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, Dakar, Senegal, and bDepartment of Chemistry and Biochemistry, University of Notre Dame, 246, Nieuwland, Science Hall, Notre Dame, IN 46557-5670, USA
*Correspondence e-mail: mouhamadoubdiop@gmail.com

Edited by H. Ishida, Okayama University, Japan (Received 27 January 2016; accepted 13 February 2016; online 24 February 2016)

The ZnII atom in the title complex, [ZnCl2(C4H6N2S2)2], is coordinated in a distorted tetra­hedral manner by two Cl atoms and two terminal N atoms of two dimethyl N-cyano­dithio­imino­carbonate ligands. In the crystal, the complex mol­ecules are connected through C—H⋯Cl hydrogen bonds and Cl⋯S contacts, leading to a two-dimensional structure extending parallel to the ab plane.

CCDC reference: 1453191

1. Chemical context

Two N and two S atoms in dimethyl N-cyano­dithio­imino­carbonate (DMCDIC), which are expected to act as hard and soft donors, respectively, according to Pearson's concept, give an inter­esting coordination potential to this mol­ecule. However, only one structure of a metal complex with DMCDIC acting as a ligand has been reported (Kojić-Prodić et al., 1992[Kojić-Prodić, B., Kiralj, R., Zlata, R. & Šunjić, V. (1992). Vestn. Slov. Kem. Drus. (Bull. Slovenian Chem. Soc.), 39, 367-381.]). Very recently, we reported the crystal structure of [CoCl2(DMCDIC)2] (Diop et al., 2016[Diop, M. B., Diop, L. & Oliver, A. G. (2016). Acta Cryst. E72, 66-68.]). Because of the scarcity of data on the coordination ability of DMCDIC, we have focused on studying the inter­actions between some transition metal halides and this ligand, which has yielded the title complex.

[Scheme 1]

2. Structural commentary

The structure of the title compound (Fig. 1[link]) is isotypic with the Co complex reported recently (Diop et al., 2016[Diop, M. B., Diop, L. & Oliver, A. G. (2016). Acta Cryst. E72, 66-68.]). The ZnII atom is coordinated in a tetra­hedral fashion by two Cl atoms and the cyanide N atoms of two dimethyl N-cyano­dithio­imino­carbonate ligands. The Zn atom has a τ4 value of 0.94 (Yang et al., 2007[Yang, L., Powell, D. R. & Houser, R. P. (2007). Dalton Trans. pp. 955-964.]), indicating a near ideal tetra­hedral geometry (τ4 = 1 for ideal tetra­hedral and 0 for planar environments); τ4 = [360 - (α + β)]/141, where α and β are the two largest tetra­hedral angles.

[Figure 1]
Figure 1
The mol­ecular structure of the title compound. Anisotropic displacement ellipsoids are depicted at the 50% probability level and H atoms as spheres of an arbitrary radius.

3. Supra­molecular features

In the crystal, weak C—H⋯Cl hydrogen bonds (C3—H3B⋯Cl1ii and C7—H7B⋯Cl1ii; Table 1[link]) link the mol­ecules into inversion dimers (Fig. 2[link]). The dimers are connected through a C4—H4B⋯Cl2i hydrogen bond (Table 1[link]) and an S2⋯Cl2i short contact [3.3812 (7) Å], giving infinite chains along [[\overline{1}]10]. These chains are then connected through a longer hydrogen bond (C7—H7A⋯Cl2ii) and an S4⋯Cl2iv contact [3.3765 (7) Å; symmetry code: (iv) x, y, z + 1], leading to a layer parallel to the ab plane (Fig. 3[link]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C4—H4B⋯Cl2i 0.98 2.73 3.4486 (18) 131
C3—H3B⋯Cl1ii 0.98 2.80 3.5868 (19) 137
C7—H7A⋯Cl2iii 0.98 2.74 3.7165 (18) 176
C7—H7B⋯Cl1ii 0.98 2.84 3.5976 (18) 134
Symmetry codes: (i) x+1, y-1, z; (ii) -x+1, -y+1, -z+1; (iii) -x+1, -y+2, -z+1.
[Figure 2]
Figure 2
Packing diagram of the title compound, viewed approximately along the c axis, showing a pair of mol­ecules. Displacement ellipsoids are as in Fig. 1[link].
[Figure 3]
Figure 3
Packing diagram of the title compound viewed approximately along the c axis. Displacement ellipsoids are as in Fig. 1[link].

4. Synthesis and crystallization

All chemicals are purchased from Aldrich Company, Germany and used as received. Dimethyl cyano­carbonimidodi­thio­ate was mixed in aceto­nitrile with ZnCl2 in a 1:1 ratio. Colourless block-like single crystals suitable for X-ray diffraction were obtained after a slow solvent evaporation at room temperature (303 K).

5. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. The structure was solved by incorporating the coordinates from the isotypic compound [Co((MeS)2CNCN)2Cl2] (Diop et al., 2016[Diop, M. B., Diop, L. & Oliver, A. G. (2016). Acta Cryst. E72, 66-68.]). Methyl H atoms were modeled as riding, with C—H = 0.98 Å and with Uiso(H) = 1.5Ueq(C), and were allowed to rotate to minimize their contribution to the electron density.

Table 2
Experimental details

Crystal data
Chemical formula [Zn(C4H6N2S2)2Cl2]
Mr 428.73
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 120
a, b, c (Å) 8.8574 (5), 8.8833 (6), 11.2391 (7)
α, β, γ (°) 73.0839 (16), 87.4301 (16), 79.9801 (16)
V (Å3) 833.14 (9)
Z 2
Radiation type Mo Kα
μ (mm−1) 2.29
Crystal size (mm) 0.49 × 0.21 × 0.17
 
Data collection
Diffractometer Bruker Kappa X8 APEXII
Absorption correction Numerical (SADABS; Krause et al., 2015[Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3-10.])
Tmin, Tmax 0.520, 0.793
No. of measured, independent and observed [I > 2σ(I)] reflections 13605, 4239, 3939
Rint 0.019
(sin θ/λ)max (Å−1) 0.673
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.025, 0.062, 1.16
No. of reflections 4239
No. of parameters 176
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.71, −0.37
Computer programs: APEX2 and SAINT (Bruker, 2015[Bruker (2015). APEX2 and SAINT. Bruker-Nonius AXS, Madison, Wisconsin, USA.]), SHELXT2014 (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2014 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]).

Supporting information

CCDC reference: 1453191

Crystal structure: contains datablock I. DOI: 10.1107/S2056989016002607/is5443sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989016002607/is5443Isup2.hkl

checkCIF report


Chemical context top

Two N and two S atoms in di­methyl N-cyano­dithio­imino­carbonate (DMCDIC), which are expected to act as hard and soft donors, respectively, according to Pearson's concept, gives an inter­esting coordination potential to this molecule. However, only one structure of metal complex with DMCDIC acting as a ligand has been reported (Kojić-Prodić et al., 1992). Very recently, we reported the crystal structure of [CoCl2(DMCDIC)2] (Diop et al., 2016). Because of the scarcity of data on the coordination ability of DMCDIC, we have focused on studying the inter­actions between some transition metal halides and this ligand, which has yielded the title complex.

Structural commentary top

The structure of the title compound (Fig. 1) is isotypic with the Co complex reported recently (Diop et al., 2016). The Zn atom is coordinated in a tetra­hedral fashion by two Cl atoms and the cyanide N atoms of two di­methyl N-cyano­dithio­imino­carbonate ligands. The Zn atom has a τ4 value of 0.94 (Yang et al., 2007), indicating a near ideal tetra­hedral geometry (τ4 = 1 for ideal tetra­hedral and 0 for planar environments); τ4 = [360 - (α + β)]/141, where α and β are the two largest tetra­hedral angles.

Supra­molecular features top

In the crystal, weak C—H···Cl hydrogen bonds (C3—H3B···Cl1ii and C7—H7B···Cl1ii; Table 1) link the molecules into inversion dimers (Fig. 2). The dimers are connected through a C4—H4B···Cl2i hydrogen bond (Table 1) and an S2···Cl2i short contact [3.3812 (7) Å], giving infinite chains along [110]. These chains are then connected through a longer hydrogen bond (C7—H7A···Cl2ii) and an S4···Cl2iv contact [3.3765 (7) Å; symmetry code: (iv) x, y, z + 1], leading to a layer parallel to the ab plane (Fig. 3).

Synthesis and crystallization top

All chemicals are purchased from Aldrich Company, Germany and used as received. Di­methyl cyano­carbonimidodi­thio­ate was mixed in aceto­nitrile with ZnCl2 in a 1:1 ratio. Colourless block-like single crystals suitable for X-ray diffraction were obtained after a slow solvent evaporation at room temperature (303 K).

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. The structure was solved by incorporating the coordinates from the isotypic compound [Co((MeS)2CNCN)2Cl2] (Diop et al., 2016). Methyl H atoms were modeled as riding, with C—H = 0.98 Å and with Uiso(H) = 1.5Ueq(C), and were allowed to rotate to minimize their contribution to the electron density.

Structure description top

Two N and two S atoms in di­methyl N-cyano­dithio­imino­carbonate (DMCDIC), which are expected to act as hard and soft donors, respectively, according to Pearson's concept, gives an inter­esting coordination potential to this molecule. However, only one structure of metal complex with DMCDIC acting as a ligand has been reported (Kojić-Prodić et al., 1992). Very recently, we reported the crystal structure of [CoCl2(DMCDIC)2] (Diop et al., 2016). Because of the scarcity of data on the coordination ability of DMCDIC, we have focused on studying the inter­actions between some transition metal halides and this ligand, which has yielded the title complex.

The structure of the title compound (Fig. 1) is isotypic with the Co complex reported recently (Diop et al., 2016). The Zn atom is coordinated in a tetra­hedral fashion by two Cl atoms and the cyanide N atoms of two di­methyl N-cyano­dithio­imino­carbonate ligands. The Zn atom has a τ4 value of 0.94 (Yang et al., 2007), indicating a near ideal tetra­hedral geometry (τ4 = 1 for ideal tetra­hedral and 0 for planar environments); τ4 = [360 - (α + β)]/141, where α and β are the two largest tetra­hedral angles.

In the crystal, weak C—H···Cl hydrogen bonds (C3—H3B···Cl1ii and C7—H7B···Cl1ii; Table 1) link the molecules into inversion dimers (Fig. 2). The dimers are connected through a C4—H4B···Cl2i hydrogen bond (Table 1) and an S2···Cl2i short contact [3.3812 (7) Å], giving infinite chains along [110]. These chains are then connected through a longer hydrogen bond (C7—H7A···Cl2ii) and an S4···Cl2iv contact [3.3765 (7) Å; symmetry code: (iv) x, y, z + 1], leading to a layer parallel to the ab plane (Fig. 3).

Synthesis and crystallization top

All chemicals are purchased from Aldrich Company, Germany and used as received. Di­methyl cyano­carbonimidodi­thio­ate was mixed in aceto­nitrile with ZnCl2 in a 1:1 ratio. Colourless block-like single crystals suitable for X-ray diffraction were obtained after a slow solvent evaporation at room temperature (303 K).

Refinement details top

Crystal data, data collection and structure refinement details are summarized in Table 2. The structure was solved by incorporating the coordinates from the isotypic compound [Co((MeS)2CNCN)2Cl2] (Diop et al., 2016). Methyl H atoms were modeled as riding, with C—H = 0.98 Å and with Uiso(H) = 1.5Ueq(C), and were allowed to rotate to minimize their contribution to the electron density.

Computing details top

Data collection: APEX2 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: Mercury (Macrae et al., 2006).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Atomic displacement ellipsoids are depicted at the 50% probability level and H atoms as spheres of an arbitrary radius.
[Figure 2] Fig. 2. Packing diagram of the title compound, viewed approximately along the c axis, showing a pair of molecules. Displacement ellipsoids are as in Fig. 1.
[Figure 3] Fig. 3. Packing diagram of the title compound viewed approximately along the c axis. Displacement ellipsoids are as in Fig. 1.
Dichloridobis(dimethyl N-cyanodithioiminocarbonate)zinc top
Crystal data top
[Zn(C4H6N2S2)2Cl2]Z = 2
Mr = 428.73F(000) = 432
Triclinic, P1Dx = 1.709 Mg m−3
a = 8.8574 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.8833 (6) ÅCell parameters from 8988 reflections
c = 11.2391 (7) Åθ = 2.3–28.6°
α = 73.0839 (16)°µ = 2.29 mm−1
β = 87.4301 (16)°T = 120 K
γ = 79.9801 (16)°Block, colourless
V = 833.14 (9) Å30.49 × 0.21 × 0.17 mm
Data collection top
Bruker Kappa X8 APEXII
diffractometer		4239 independent reflections
Radiation source: fine-focus sealed tube3939 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
Detector resolution: 8.33 pixels mm-1θmax = 28.6°, θmin = 1.9°
combination of ω and φ–scansh = −11→11
Absorption correction: numerical
(SADABS; Krause et al., 2015)		k = −9→11
Tmin = 0.520, Tmax = 0.793l = −14→15
13605 measured reflections
Refinement top
Refinement on F2Primary atom site location: isomorphous structure methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.025Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.062H-atom parameters constrained
S = 1.16 w = 1/[σ2(Fo2) + (0.0275P)2 + 0.4996P]
where P = (Fo2 + 2Fc2)/3
4239 reflections(Δ/σ)max = 0.001
176 parametersΔρmax = 0.71 e Å−3
0 restraintsΔρmin = −0.37 e Å−3
Crystal data top
[Zn(C4H6N2S2)2Cl2]γ = 79.9801 (16)°
Mr = 428.73V = 833.14 (9) Å3
Triclinic, P1Z = 2
a = 8.8574 (5) ÅMo Kα radiation
b = 8.8833 (6) ŵ = 2.29 mm−1
c = 11.2391 (7) ÅT = 120 K
α = 73.0839 (16)°0.49 × 0.21 × 0.17 mm
β = 87.4301 (16)°
Data collection top
Bruker Kappa X8 APEXII
diffractometer		4239 independent reflections
Absorption correction: numerical
(SADABS; Krause et al., 2015)		3939 reflections with I > 2σ(I)
Tmin = 0.520, Tmax = 0.793Rint = 0.019
13605 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0250 restraints
wR(F2) = 0.062H-atom parameters constrained
S = 1.16Δρmax = 0.71 e Å−3
4239 reflectionsΔρmin = −0.37 e Å−3
176 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn10.31840 (2)0.80108 (2)0.23625 (2)0.01602 (6)
Cl10.16956 (5)0.61543 (5)0.29276 (4)0.02386 (9)
Cl20.23470 (5)1.01274 (5)0.08093 (4)0.02331 (9)
S10.83793 (5)0.41654 (5)0.37573 (4)0.01844 (9)
S20.97579 (4)0.27942 (5)0.17752 (4)0.01855 (9)
S30.53848 (5)0.72562 (5)0.68555 (4)0.01877 (9)
S40.35318 (5)0.94788 (5)0.80760 (4)0.01798 (9)
N10.52396 (16)0.69240 (17)0.19696 (14)0.0216 (3)
N20.73637 (16)0.50808 (17)0.14285 (13)0.0186 (3)
N30.34751 (18)0.87159 (18)0.38602 (13)0.0223 (3)
N40.31171 (17)0.95551 (17)0.57596 (13)0.0192 (3)
C10.62644 (18)0.60463 (19)0.17805 (15)0.0178 (3)
C20.83921 (17)0.41281 (18)0.22362 (15)0.0163 (3)
C31.0004 (2)0.2705 (2)0.44393 (16)0.0248 (3)
H3A0.98860.16660.43510.037*
H3B1.00750.26280.53230.037*
H3C1.09400.30230.40160.037*
C40.9182 (2)0.3114 (2)0.01991 (15)0.0230 (3)
H4A0.81230.29340.01840.034*
H4B0.98590.2369−0.01640.034*
H4C0.92490.4213−0.02850.034*
C50.33745 (19)0.90393 (19)0.47793 (15)0.0189 (3)
C60.39261 (18)0.88406 (19)0.67851 (15)0.0170 (3)
C70.6027 (2)0.6667 (2)0.84453 (16)0.0228 (3)
H7A0.64170.75500.86170.034*
H7B0.68450.57360.85860.034*
H7C0.51670.63930.90000.034*
C80.1918 (2)1.1031 (2)0.75497 (17)0.0237 (3)
H8A0.22091.18400.68170.036*
H8B0.15901.15260.82130.036*
H8C0.10751.05780.73300.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.01630 (10)0.01660 (10)0.01569 (10)0.00008 (7)0.00063 (7)−0.00723 (7)
Cl10.02395 (19)0.0244 (2)0.0270 (2)−0.00800 (15)0.00604 (15)−0.01198 (16)
Cl20.0288 (2)0.01982 (19)0.01917 (18)0.00453 (15)−0.00438 (15)−0.00668 (15)
S10.01807 (18)0.02036 (19)0.01693 (18)−0.00120 (14)0.00170 (14)−0.00684 (14)
S20.01730 (18)0.01884 (19)0.01817 (18)0.00245 (14)0.00138 (14)−0.00662 (14)
S30.02048 (18)0.01800 (19)0.01854 (19)−0.00125 (14)0.00216 (14)−0.00781 (14)
S40.02055 (18)0.01868 (19)0.01489 (17)0.00057 (14)−0.00022 (14)−0.00732 (14)
N10.0190 (7)0.0186 (7)0.0253 (7)0.0010 (5)0.0018 (5)−0.0062 (6)
N20.0176 (6)0.0185 (6)0.0183 (6)0.0011 (5)0.0019 (5)−0.0058 (5)
N30.0292 (7)0.0225 (7)0.0165 (7)−0.0065 (6)0.0013 (5)−0.0069 (5)
N40.0243 (7)0.0190 (7)0.0150 (6)−0.0034 (5)0.0006 (5)−0.0063 (5)
C10.0193 (7)0.0165 (7)0.0172 (7)−0.0032 (6)−0.0001 (6)−0.0040 (6)
C20.0151 (7)0.0153 (7)0.0186 (7)−0.0032 (5)0.0031 (5)−0.0052 (6)
C30.0242 (8)0.0278 (9)0.0189 (8)0.0018 (7)−0.0031 (6)−0.0044 (7)
C40.0245 (8)0.0267 (9)0.0174 (8)0.0016 (7)0.0007 (6)−0.0094 (6)
C50.0219 (8)0.0165 (7)0.0183 (7)−0.0058 (6)0.0011 (6)−0.0036 (6)
C60.0193 (7)0.0162 (7)0.0168 (7)−0.0052 (6)0.0027 (6)−0.0060 (6)
C70.0221 (8)0.0236 (8)0.0230 (8)0.0017 (6)−0.0043 (6)−0.0097 (7)
C80.0256 (8)0.0212 (8)0.0229 (8)0.0049 (6)−0.0024 (6)−0.0090 (7)
Geometric parameters (Å, º) top
Zn1—N32.0003 (15)N3—C51.146 (2)
Zn1—N12.0016 (14)N4—C51.308 (2)
Zn1—Cl22.2030 (4)N4—C61.317 (2)
Zn1—Cl12.2210 (4)C3—H3A0.9800
S1—C21.7191 (17)C3—H3B0.9800
S1—C31.7922 (18)C3—H3C0.9800
S2—C21.7141 (16)C4—H4A0.9800
S2—C41.7935 (17)C4—H4B0.9800
S3—C61.7228 (17)C4—H4C0.9800
S3—C71.7980 (17)C7—H7A0.9800
S4—C61.7067 (16)C7—H7B0.9800
S4—C81.7914 (17)C7—H7C0.9800
N1—C11.144 (2)C8—H8A0.9800
N2—C11.309 (2)C8—H8B0.9800
N2—C21.315 (2)C8—H8C0.9800
N3—Zn1—N1106.61 (6)H3B—C3—H3C109.5
N3—Zn1—Cl2108.82 (5)S2—C4—H4A109.5
N1—Zn1—Cl2110.62 (4)S2—C4—H4B109.5
N3—Zn1—Cl1107.09 (4)H4A—C4—H4B109.5
N1—Zn1—Cl1106.71 (4)S2—C4—H4C109.5
Cl2—Zn1—Cl1116.505 (19)H4A—C4—H4C109.5
C2—S1—C3103.78 (8)H4B—C4—H4C109.5
C2—S2—C4101.50 (8)N3—C5—N4172.64 (19)
C6—S3—C7103.40 (8)N4—C6—S4119.94 (13)
C6—S4—C8101.30 (8)N4—C6—S3121.19 (12)
C1—N1—Zn1166.17 (14)S4—C6—S3118.87 (9)
C1—N2—C2120.32 (15)S3—C7—H7A109.5
C5—N3—Zn1166.98 (14)S3—C7—H7B109.5
C5—N4—C6120.40 (15)H7A—C7—H7B109.5
N1—C1—N2172.98 (18)S3—C7—H7C109.5
N2—C2—S2119.54 (12)H7A—C7—H7C109.5
N2—C2—S1121.40 (12)H7B—C7—H7C109.5
S2—C2—S1119.05 (9)S4—C8—H8A109.5
S1—C3—H3A109.5S4—C8—H8B109.5
S1—C3—H3B109.5H8A—C8—H8B109.5
H3A—C3—H3B109.5S4—C8—H8C109.5
S1—C3—H3C109.5H8A—C8—H8C109.5
H3A—C3—H3C109.5H8B—C8—H8C109.5
C1—N2—C2—S2176.35 (12)C5—N4—C6—S4−177.58 (12)
C1—N2—C2—S1−2.5 (2)C5—N4—C6—S32.2 (2)
C4—S2—C2—N2−3.57 (15)C8—S4—C6—N42.39 (15)
C4—S2—C2—S1175.32 (10)C8—S4—C6—S3−177.42 (10)
C3—S1—C2—N2−178.77 (14)C7—S3—C6—N4−176.93 (14)
C3—S1—C2—S22.36 (12)C7—S3—C6—S42.89 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4B···Cl2i0.982.733.4486 (18)131
C3—H3B···Cl1ii0.982.803.5868 (19)137
C7—H7A···Cl2iii0.982.743.7165 (18)176
C7—H7B···Cl1ii0.982.843.5976 (18)134
Symmetry codes: (i) x+1, y−1, z; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+2, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4B···Cl2i0.982.733.4486 (18)131
C3—H3B···Cl1ii0.982.803.5868 (19)137
C7—H7A···Cl2iii0.982.743.7165 (18)176
C7—H7B···Cl1ii0.982.843.5976 (18)134
Symmetry codes: (i) x+1, y−1, z; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula[Zn(C4H6N2S2)2Cl2]
Mr428.73
Crystal system, space groupTriclinic, P1
Temperature (K)120
a, b, c (Å)8.8574 (5), 8.8833 (6), 11.2391 (7)
α, β, γ (°)73.0839 (16), 87.4301 (16), 79.9801 (16)
V (Å3)833.14 (9)
Z2
Radiation typeMo Kα
µ (mm−1)2.29
Crystal size (mm)0.49 × 0.21 × 0.17
Data collection
DiffractometerBruker Kappa X8 APEXII
Absorption correctionNumerical
(SADABS; Krause et al., 2015)
Tmin, Tmax0.520, 0.793
No. of measured, independent and
observed [I > 2σ(I)] reflections		13605, 4239, 3939
Rint0.019
(sin θ/λ)max (Å−1)0.673
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.025, 0.062, 1.16
No. of reflections4239
No. of parameters176
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.71, −0.37

Computer programs: APEX2 (Bruker, 2015), SAINT (Bruker, 2015), SHELXT2014 (Sheldrick, 2015a), SHELXL2014 (Sheldrick, 2015b), XP in SHELXTL (Sheldrick, 2008), Mercury (Macrae et al., 2006).

 

Acknowledgements

The authors acknowledge Cheikh Anta Diop University of Dakar (Sénégal) and the University of Notre Dame (USA) for financial support.

References

First citationBruker (2015). APEX2 and SAINT. Bruker–Nonius AXS, Madison, Wisconsin, USA.  Google Scholar
 First citationDiop, M. B., Diop, L. & Oliver, A. G. (2016). Acta Cryst. E72, 66–68.  CSD CrossRef IUCr Journals Google Scholar
 First citationKojić-Prodić, B., Kiralj, R., Zlata, R. & Šunjić, V. (1992). Vestn. Slov. Kem. Drus. (Bull. Slovenian Chem. Soc.), 39, 367–381.  Google Scholar
 First citationKrause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3–10.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationMacrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationYang, L., Powell, D. R. & Houser, R. P. (2007). Dalton Trans. pp. 955–964.  Web of Science CSD CrossRef PubMed 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.

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ISSN: 2056-9890
Volume 72| Part 3| March 2016| Pages 417-419
doi:10.1107/S2056989016002607
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