organic compounds
Dimethyl N-cyanodithioiminocarbonate
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, Notre Dame, IN 46557-5670, USA
*Correspondence e-mail: mouhamadoubdiop@gmail.com
The title compound, C4H6N2S2, crystallizes with four independent molecules in the Two of the molecules are disordered about a pseudo twofold rotation axis. The mean values of the C—N bonds are 1.143 (5) Å for C≡N, 1.302 (5) Å for C=N and 1.341 (5) Å for the C—N single bond. In the crystal, molecules are linked via C—H⋯N hydrogen bonds, forming slabs parallel to the bc plane.
Keywords: crystal structure; cyano; thioate; C—H⋯N hydrogen bonds.
CCDC reference: 1468943
Structure description
Dimethyl cyaniminodithiocarbamate with its potential coordination power – two N and two S atoms – has been scarcely studied. To the best of our knowledge, only two crystalline structures incorporating this ligand are known, viz. catena-[bis(μ2-chloro)bis[2,2-bis(methylthio)-N-cyanoazomethine]copper(I)] (Kojić-Prodić et al., 1992) and dichloridobis(dimethyl N-cyanodithioiminocarbonate)cobalt (II) (Diop et al., 2016). In our study of new compounds containing this ligand, we have undertaken reactions between the title compound, dimethyl cyanocarbonimidodithioate, and CrO2Cl2 expecting coordination to the Cr atom. However, only crystals of the title ligand were obtained and we report herein on its crystal structure.
The molecular structures of the four independent molecules (A, B, C and D) of the title compound are illustrated in Fig. 1. Two of the molecules, B and D, were found to have a small, but significant amount of disorder in the position of the sulfur atoms. The imido nitrogen and cyanide carbon are disordered in these two molecules, reflecting the orientation change of the methylthiol chains (Fig. 1). Bond lengths and angles in the major component and fully occupied molecules are in the expected ranges (Diop et al., 2016) and show perfect planarity around the imido carbon atoms (average sum of angles is 359.99°).
In the crystal, C—H⋯N hydrogen bonds link the four molecules, forming slabs that lie parallel to (100); see Table 1 and Fig. 2.
Synthesis and crystallization
Dimethyl cyanocarbonimidodithioate was mixed in acetonitrile with CrO2Cl2 in a 1:1 ratio, giving a green solution. On slow evaporation of the solution at room temperature (303 K), a small number of colourless crystals of the title compound were obtained.
Refinement
Crystal data, data collection and structure . The disordered components of molecules B and D were refined with the occupancy of the disorder components summed to unity. The occupancy of each molecule was refined separately yielding a 0.92:0.08 and 0.90:0.10 ratio. Despite this small percentage, there was a significant improvement in the model upon inclusion of this disorder. The atomic displacement parameters of the inherent minor disordered component present in the cyanide nitrogen and carbon atoms were restrained to be similar to those of the associated major component.
details are summarized in Table 2Structural data
CCDC reference: 1468943
10.1107/S2414314616004545/su4016sup1.cif
contains datablocks I, Global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616004545/su4016Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616004545/su4016Isup3.cml
Dimethyl cyanocarbonimidodithioate was mixed in acetonitrile with CrO2Cl2 in a 1:1 ratio, giving a green solution. On slow evaporation of the solution at room temperature (303 K), a small number of colourless crystals of the title compound were obtained.
Crystal data, data collection and structure
details are summarized in Table 2. The disordered components of molecules B and D were refined with the occupancy of the disorder components summed to unity. The occupancy of each molecule was refined separately yielding a 0.92:0.08 and 0.90:0.10 ratio. Despite this small percentage, there was a significant improvement in the model upon inclusion of this disorder. The atomic displacement parameters of the inherent minor disordered component present in the cyanide nitrogen and carbon atoms were restrained to be similar to those of the associated major component.Dimethyl cyaniminodithiocarbamate with its potential coordination power – two N and two S atoms – has been scarcely studied. To the best of our knowledge, only two crystalline structures incorporating this ligand are known, viz. catena-[bis(µ2-chloro)-bis[2,2-bis(methylthio)-N-cyanoazomethine]copper(I)] (Kojić-Prodić et al., 1992) and dichloridobis(dimethyl N-cyanodithioiminocarbonate)zinc (Diop et al., 2016). In our study of new compounds containing this ligand, we have undertaken reactions between the title compound, dimethyl cyanocarbonimidodithioate, and CrO2Cl2 expecting coordination to the Cr atom. However, only crystals of the title ligand were obtained and we report herein on its crystal structure.
The molecular structure of the four independent molecules (A, B, C and D) of the title compound is illustrated in Fig. 1. Two of the molecules, B and D, were found to have a small, but significant amount of disorder in the position of the sulfur atoms. The imido nitrogen and cyanide carbon are disordered in these two molecules, reflecting the orientation change of the methylthiol chains (Fig. 1). Bond lengths and angles in the major component and fully occupied molecules are in the expected ranges (Diop et al., 2016) and show perfect planarity around the imido carbon atoms (average sum of angles is 359.99°).
In the crystal, C—H···N hydrogen bonds link the four molecules, forming slabs that lie parallel to (100); see Table 1 and Fig. 2.
Data collection: APEX3 (Bruker, 2015); cell
SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b) and publCIF (Westrip, 2010).Fig. 1. The molecular structure of the four independent molecules (A, B, C and D) of the title compound, with atom labelling. The minor components of the disordered molecules are shown with dashed bonds. Displacement ellipsoids are drawn at the 50% probability level. | |
Fig. 2. The crystal packing of the title compound, viewed approximately along the b-axis direction. The four independent molecules (A green, B black, C blue, D red) are linked via C—H···N hydrogen bonds (dashed lines; see Table 1). |
C4H6N2S2 | F(000) = 1216 |
Mr = 146.23 | Dx = 1.462 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 15.2211 (18) Å | Cell parameters from 2731 reflections |
b = 12.2037 (15) Å | θ = 2.5–24.0° |
c = 14.4716 (18) Å | µ = 0.69 mm−1 |
β = 98.788 (5)° | T = 120 K |
V = 2656.6 (6) Å3 | Plate, colourless |
Z = 16 | 0.19 × 0.12 × 0.04 mm |
Bruker Kappa X8 APEXIII diffractometer | 4868 independent reflections |
Radiation source: fine-focus sealed tube | 2986 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.105 |
Detector resolution: 8.33 pixels mm-1 | θmax = 25.4°, θmin = 1.4° |
ω and φ–scans | h = −18→18 |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | k = −10→14 |
Tmin = 0.837, Tmax = 0.983 | l = −17→17 |
36932 measured reflections |
Refinement on F2 | Primary atom site location: real-space vector search |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0335P)2 + 2.1088P] where P = (Fo2 + 2Fc2)/3 |
4868 reflections | (Δ/σ)max = 0.002 |
331 parameters | Δρmax = 0.86 e Å−3 |
24 restraints | Δρmin = −0.37 e Å−3 |
C4H6N2S2 | V = 2656.6 (6) Å3 |
Mr = 146.23 | Z = 16 |
Monoclinic, P21/c | Mo Kα radiation |
a = 15.2211 (18) Å | µ = 0.69 mm−1 |
b = 12.2037 (15) Å | T = 120 K |
c = 14.4716 (18) Å | 0.19 × 0.12 × 0.04 mm |
β = 98.788 (5)° |
Bruker Kappa X8 APEXIII diffractometer | 4868 independent reflections |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | 2986 reflections with I > 2σ(I) |
Tmin = 0.837, Tmax = 0.983 | Rint = 0.105 |
36932 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 24 restraints |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.86 e Å−3 |
4868 reflections | Δρmin = −0.37 e Å−3 |
331 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1A | 0.23225 (6) | 0.34721 (9) | 0.68456 (7) | 0.0256 (3) | |
S2A | 0.42019 (6) | 0.30624 (9) | 0.66254 (7) | 0.0247 (3) | |
N1A | 0.4260 (2) | 0.0211 (3) | 0.6710 (3) | 0.0346 (9) | |
N2A | 0.3025 (2) | 0.1506 (3) | 0.6812 (2) | 0.0240 (8) | |
C1A | 0.3717 (3) | 0.0847 (4) | 0.6751 (3) | 0.0278 (10) | |
C2A | 0.3160 (2) | 0.2562 (3) | 0.6760 (3) | 0.0212 (9) | |
C3A | 0.1432 (2) | 0.2571 (3) | 0.6995 (3) | 0.0290 (10) | |
H3AA | 0.1318 | 0.2071 | 0.6461 | 0.044* | |
H3AB | 0.0895 | 0.3000 | 0.7037 | 0.044* | |
H3AC | 0.1593 | 0.2146 | 0.7571 | 0.044* | |
C4A | 0.4042 (3) | 0.4514 (3) | 0.6502 (3) | 0.0282 (10) | |
H4AA | 0.3580 | 0.4664 | 0.5968 | 0.042* | |
H4AB | 0.4600 | 0.4860 | 0.6397 | 0.042* | |
H4AC | 0.3860 | 0.4812 | 0.7072 | 0.042* | |
S1B | 0.27136 (7) | 0.84989 (10) | 0.67592 (8) | 0.0282 (3) | 0.912 (2) |
S2B | 0.08290 (7) | 0.80878 (10) | 0.69178 (8) | 0.0272 (3) | 0.912 (2) |
N2B | 0.2056 (2) | 0.6533 (3) | 0.6944 (2) | 0.0229 (8) | 0.912 (2) |
C1B | 0.1383 (3) | 0.5860 (4) | 0.7034 (3) | 0.0272 (12) | 0.912 (2) |
S1BA | 0.1982 (7) | 0.9020 (9) | 0.6848 (7) | 0.018 (3)* | 0.088 (2) |
S2BA | 0.2706 (7) | 0.6740 (8) | 0.6838 (7) | 0.015 (3)* | 0.088 (2) |
N2BA | 0.106 (2) | 0.732 (3) | 0.702 (3) | 0.023 (3)* | 0.088 (2) |
C1BA | 0.095 (4) | 0.607 (5) | 0.705 (4) | 0.026 (3)* | 0.088 (2) |
N1B | 0.0844 (2) | 0.5224 (3) | 0.7107 (2) | 0.0334 (9) | |
C2B | 0.1882 (2) | 0.7574 (3) | 0.6888 (3) | 0.0223 (9) | |
C3B | 0.3641 (3) | 0.7605 (3) | 0.6732 (3) | 0.0319 (11) | |
H3BA | 0.3789 | 0.7239 | 0.7338 | 0.048* | 0.912 (2) |
H3BB | 0.4153 | 0.8033 | 0.6602 | 0.048* | 0.912 (2) |
H3BC | 0.3488 | 0.7055 | 0.6240 | 0.048* | 0.912 (2) |
H3BD | 0.3507 | 0.8053 | 0.6165 | 0.048* | 0.088 (2) |
H3BE | 0.4164 | 0.7150 | 0.6692 | 0.048* | 0.088 (2) |
H3BF | 0.3760 | 0.8085 | 0.7280 | 0.048* | 0.088 (2) |
C4B | 0.0934 (3) | 0.9533 (3) | 0.6822 (3) | 0.0319 (11) | |
H4BA | 0.1391 | 0.9799 | 0.7323 | 0.048* | 0.912 (2) |
H4BB | 0.0365 | 0.9882 | 0.6875 | 0.048* | 0.912 (2) |
H4BC | 0.1106 | 0.9714 | 0.6214 | 0.048* | 0.912 (2) |
H4BD | 0.0941 | 1.0097 | 0.7305 | 0.048* | 0.088 (2) |
H4BE | 0.0531 | 0.8940 | 0.6939 | 0.048* | 0.088 (2) |
H4BF | 0.0730 | 0.9855 | 0.6206 | 0.048* | 0.088 (2) |
S1C | 0.59095 (7) | −0.06797 (9) | 0.58903 (7) | 0.0273 (3) | |
S2C | 0.70112 (7) | −0.26439 (9) | 0.57075 (8) | 0.0274 (3) | |
N1C | 0.9006 (2) | −0.1351 (3) | 0.5268 (2) | 0.0347 (9) | |
N2C | 0.7551 (2) | −0.0593 (3) | 0.5548 (2) | 0.0280 (8) | |
C1C | 0.8319 (3) | −0.1058 (3) | 0.5399 (3) | 0.0286 (10) | |
C2C | 0.6907 (3) | −0.1234 (3) | 0.5689 (3) | 0.0205 (9) | |
C3C | 0.6149 (3) | 0.0749 (3) | 0.5822 (3) | 0.0312 (10) | |
H3CA | 0.6665 | 0.0932 | 0.6289 | 0.047* | |
H3CB | 0.5633 | 0.1176 | 0.5944 | 0.047* | |
H3CC | 0.6280 | 0.0922 | 0.5196 | 0.047* | |
C4C | 0.5942 (2) | −0.3166 (3) | 0.5872 (3) | 0.0248 (10) | |
H4CA | 0.5770 | −0.2846 | 0.6439 | 0.037* | |
H4CB | 0.5974 | −0.3965 | 0.5936 | 0.037* | |
H4CC | 0.5500 | −0.2973 | 0.5331 | 0.037* | |
S1D | 0.91532 (7) | 0.31363 (9) | 0.54631 (8) | 0.0239 (3) | 0.906 (2) |
S2D | 0.79660 (7) | 0.50375 (9) | 0.55930 (8) | 0.0264 (3) | 0.906 (2) |
N2D | 0.7486 (2) | 0.2970 (3) | 0.5728 (2) | 0.0243 (9) | 0.906 (2) |
C1D | 0.6687 (4) | 0.3409 (4) | 0.5792 (4) | 0.0274 (13) | 0.906 (2) |
S1DA | 0.9169 (6) | 0.4230 (9) | 0.5617 (7) | 0.019 (3)* | 0.094 (2) |
S2DA | 0.7999 (7) | 0.2306 (9) | 0.5670 (7) | 0.019 (3)* | 0.094 (2) |
N2DA | 0.748 (2) | 0.437 (3) | 0.571 (2) | 0.026 (3)* | 0.094 (2) |
C1DA | 0.663 (5) | 0.384 (5) | 0.569 (4) | 0.028 (3)* | 0.094 (2) |
N1D | 0.5982 (2) | 0.3688 (3) | 0.5835 (3) | 0.0347 (9) | |
C2D | 0.8131 (2) | 0.3638 (3) | 0.5613 (3) | 0.0190 (9) | |
C3D | 0.9013 (3) | 0.1702 (3) | 0.5593 (3) | 0.0259 (10) | |
H3DA | 0.8916 | 0.1542 | 0.6233 | 0.039* | 0.906 (2) |
H3DB | 0.9548 | 0.1319 | 0.5465 | 0.039* | 0.906 (2) |
H3DC | 0.8499 | 0.1453 | 0.5152 | 0.039* | 0.906 (2) |
H3DD | 0.9385 | 0.1711 | 0.6208 | 0.039* | 0.094 (2) |
H3DE | 0.9311 | 0.2109 | 0.5146 | 0.039* | 0.094 (2) |
H3DF | 0.8918 | 0.0942 | 0.5380 | 0.039* | 0.094 (2) |
C4D | 0.8994 (2) | 0.5620 (3) | 0.5400 (3) | 0.0306 (10) | |
H4DA | 0.9441 | 0.5511 | 0.5956 | 0.046* | 0.906 (2) |
H4DB | 0.8914 | 0.6407 | 0.5277 | 0.046* | 0.906 (2) |
H4DC | 0.9192 | 0.5265 | 0.4861 | 0.046* | 0.906 (2) |
H4DD | 0.9463 | 0.6043 | 0.5780 | 0.046* | 0.094 (2) |
H4DE | 0.8414 | 0.5832 | 0.5561 | 0.046* | 0.094 (2) |
H4DF | 0.9004 | 0.5769 | 0.4736 | 0.046* | 0.094 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1A | 0.0203 (5) | 0.0274 (6) | 0.0291 (6) | 0.0038 (5) | 0.0044 (4) | 0.0013 (5) |
S2A | 0.0189 (5) | 0.0278 (6) | 0.0274 (6) | 0.0009 (5) | 0.0036 (4) | 0.0017 (5) |
N1A | 0.031 (2) | 0.031 (2) | 0.046 (2) | 0.0022 (19) | 0.0149 (18) | 0.0002 (18) |
N2A | 0.0201 (18) | 0.027 (2) | 0.026 (2) | 0.0028 (16) | 0.0042 (14) | 0.0004 (16) |
C1A | 0.026 (2) | 0.026 (3) | 0.032 (3) | −0.005 (2) | 0.0073 (19) | 0.001 (2) |
C2A | 0.020 (2) | 0.028 (3) | 0.014 (2) | 0.0026 (18) | −0.0016 (16) | 0.0002 (17) |
C3A | 0.019 (2) | 0.034 (3) | 0.034 (3) | 0.0008 (19) | 0.0062 (19) | −0.003 (2) |
C4A | 0.028 (2) | 0.024 (2) | 0.033 (3) | −0.0053 (19) | 0.0051 (19) | 0.008 (2) |
S1B | 0.0238 (6) | 0.0277 (7) | 0.0331 (7) | −0.0003 (5) | 0.0045 (5) | 0.0012 (6) |
S2B | 0.0227 (6) | 0.0288 (8) | 0.0311 (7) | 0.0032 (5) | 0.0070 (5) | 0.0027 (6) |
N2B | 0.021 (2) | 0.0211 (19) | 0.026 (2) | 0.0025 (17) | 0.0009 (15) | 0.0005 (16) |
C1B | 0.027 (3) | 0.026 (3) | 0.028 (2) | 0.004 (2) | 0.003 (2) | −0.002 (2) |
N1B | 0.027 (2) | 0.036 (2) | 0.038 (2) | −0.0022 (19) | 0.0065 (17) | 0.0002 (19) |
C2B | 0.016 (2) | 0.030 (3) | 0.020 (2) | −0.0035 (19) | 0.0013 (17) | −0.0009 (19) |
C3B | 0.021 (2) | 0.034 (3) | 0.041 (3) | −0.002 (2) | 0.0040 (19) | −0.001 (2) |
C4B | 0.030 (2) | 0.027 (3) | 0.039 (3) | 0.009 (2) | 0.009 (2) | 0.001 (2) |
S1C | 0.0234 (6) | 0.0266 (6) | 0.0325 (6) | 0.0013 (5) | 0.0065 (5) | −0.0002 (5) |
S2C | 0.0254 (6) | 0.0278 (6) | 0.0294 (6) | 0.0012 (5) | 0.0054 (5) | −0.0028 (5) |
N1C | 0.023 (2) | 0.044 (3) | 0.038 (2) | 0.0007 (18) | 0.0068 (17) | 0.0020 (19) |
N2C | 0.0251 (18) | 0.031 (2) | 0.029 (2) | −0.0032 (18) | 0.0058 (15) | 0.0031 (17) |
C1C | 0.025 (3) | 0.032 (3) | 0.027 (3) | −0.003 (2) | −0.003 (2) | 0.003 (2) |
C2C | 0.025 (2) | 0.021 (2) | 0.013 (2) | 0.0006 (18) | −0.0015 (17) | 0.0003 (17) |
C3C | 0.033 (3) | 0.018 (2) | 0.043 (3) | 0.003 (2) | 0.008 (2) | 0.003 (2) |
C4C | 0.026 (2) | 0.025 (2) | 0.025 (2) | −0.0024 (19) | 0.0062 (18) | −0.0044 (19) |
S1D | 0.0183 (6) | 0.0252 (7) | 0.0289 (7) | 0.0019 (5) | 0.0057 (5) | 0.0028 (5) |
S2D | 0.0203 (6) | 0.0226 (7) | 0.0369 (7) | 0.0004 (5) | 0.0063 (5) | 0.0020 (6) |
N2D | 0.0216 (19) | 0.023 (2) | 0.029 (2) | 0.0009 (17) | 0.0066 (16) | 0.0011 (17) |
C1D | 0.029 (3) | 0.024 (3) | 0.030 (3) | −0.006 (3) | 0.006 (2) | 0.003 (2) |
N1D | 0.019 (2) | 0.038 (2) | 0.047 (2) | 0.0007 (18) | 0.0083 (17) | 0.0005 (19) |
C2D | 0.022 (2) | 0.018 (2) | 0.017 (2) | −0.0032 (18) | 0.0034 (16) | 0.0033 (17) |
C3D | 0.030 (2) | 0.021 (2) | 0.028 (2) | 0.0073 (19) | 0.0076 (18) | 0.0015 (19) |
C4D | 0.024 (2) | 0.027 (3) | 0.041 (3) | −0.004 (2) | 0.007 (2) | 0.003 (2) |
S1A—C2A | 1.709 (4) | S1C—C2C | 1.726 (4) |
S1A—C3A | 1.785 (4) | S1C—C3C | 1.787 (4) |
S2A—C2A | 1.738 (4) | S2C—C2C | 1.727 (4) |
S2A—C4A | 1.794 (4) | S2C—C4C | 1.797 (4) |
N1A—C1A | 1.143 (5) | N1C—C1C | 1.147 (5) |
N2A—C2A | 1.309 (5) | N2C—C2C | 1.295 (5) |
N2A—C1A | 1.339 (5) | N2C—C1C | 1.347 (5) |
C3A—H3AA | 0.9800 | C3C—H3CA | 0.9800 |
C3A—H3AB | 0.9800 | C3C—H3CB | 0.9800 |
C3A—H3AC | 0.9800 | C3C—H3CC | 0.9800 |
C4A—H4AA | 0.9800 | C4C—H4CA | 0.9800 |
C4A—H4AB | 0.9800 | C4C—H4CB | 0.9800 |
C4A—H4AC | 0.9800 | C4C—H4CC | 0.9800 |
S1B—C2B | 1.727 (4) | S1D—C2D | 1.717 (4) |
S1B—C3B | 1.788 (4) | S1D—C3D | 1.777 (4) |
S2B—C2B | 1.728 (4) | S2D—C2D | 1.725 (4) |
S2B—C4B | 1.778 (4) | S2D—C4D | 1.779 (4) |
N2B—C2B | 1.297 (5) | N2D—C2D | 1.306 (5) |
N2B—C1B | 1.336 (6) | N2D—C1D | 1.344 (7) |
C1B—N1B | 1.145 (6) | C1D—N1D | 1.136 (6) |
S1BA—C4B | 1.707 (11) | S1DA—C2D | 1.736 (10) |
S1BA—C2B | 1.773 (12) | S1DA—C4D | 1.740 (11) |
S2BA—C2B | 1.625 (11) | S2DA—C2D | 1.642 (11) |
S2BA—C3B | 1.797 (12) | S2DA—C3D | 1.730 (11) |
N2BA—C2B | 1.32 (4) | N2DA—C2D | 1.36 (3) |
N2BA—C1BA | 1.55 (7) | N2DA—C1DA | 1.43 (7) |
C1BA—N1B | 1.05 (6) | C1DA—N1D | 1.06 (7) |
C3B—H3BA | 0.9800 | C3D—H3DA | 0.9800 |
C3B—H3BB | 0.9800 | C3D—H3DB | 0.9800 |
C3B—H3BC | 0.9800 | C3D—H3DC | 0.9800 |
C3B—H3BD | 0.9800 | C3D—H3DD | 0.9800 |
C3B—H3BE | 0.9800 | C3D—H3DE | 0.9800 |
C3B—H3BF | 0.9800 | C3D—H3DF | 0.9800 |
C4B—H4BA | 0.9800 | C4D—H4DA | 0.9800 |
C4B—H4BB | 0.9800 | C4D—H4DB | 0.9800 |
C4B—H4BC | 0.9800 | C4D—H4DC | 0.9800 |
C4B—H4BD | 0.9800 | C4D—H4DD | 0.9800 |
C4B—H4BE | 0.9800 | C4D—H4DE | 0.9800 |
C4B—H4BF | 0.9800 | C4D—H4DF | 0.9800 |
C2A—S1A—C3A | 101.4 (2) | C2C—S1C—C3C | 100.45 (19) |
C2A—S2A—C4A | 104.26 (19) | C2C—S2C—C4C | 105.78 (19) |
C2A—N2A—C1A | 117.1 (3) | C2C—N2C—C1C | 117.9 (4) |
N1A—C1A—N2A | 174.1 (4) | N1C—C1C—N2C | 173.3 (5) |
N2A—C2A—S1A | 120.7 (3) | N2C—C2C—S1C | 119.7 (3) |
N2A—C2A—S2A | 120.4 (3) | N2C—C2C—S2C | 122.3 (3) |
S1A—C2A—S2A | 118.9 (2) | S1C—C2C—S2C | 118.0 (2) |
S1A—C3A—H3AA | 109.5 | S1C—C3C—H3CA | 109.5 |
S1A—C3A—H3AB | 109.5 | S1C—C3C—H3CB | 109.5 |
H3AA—C3A—H3AB | 109.5 | H3CA—C3C—H3CB | 109.5 |
S1A—C3A—H3AC | 109.5 | S1C—C3C—H3CC | 109.5 |
H3AA—C3A—H3AC | 109.5 | H3CA—C3C—H3CC | 109.5 |
H3AB—C3A—H3AC | 109.5 | H3CB—C3C—H3CC | 109.5 |
S2A—C4A—H4AA | 109.5 | S2C—C4C—H4CA | 109.5 |
S2A—C4A—H4AB | 109.5 | S2C—C4C—H4CB | 109.5 |
H4AA—C4A—H4AB | 109.5 | H4CA—C4C—H4CB | 109.5 |
S2A—C4A—H4AC | 109.5 | S2C—C4C—H4CC | 109.5 |
H4AA—C4A—H4AC | 109.5 | H4CA—C4C—H4CC | 109.5 |
H4AB—C4A—H4AC | 109.5 | H4CB—C4C—H4CC | 109.5 |
C2B—S1B—C3B | 101.4 (2) | C2D—S1D—C3D | 102.28 (18) |
C2B—S2B—C4B | 105.2 (2) | C2D—S2D—C4D | 105.62 (19) |
C2B—N2B—C1B | 117.1 (4) | C2D—N2D—C1D | 117.7 (4) |
N1B—C1B—N2B | 175.4 (5) | N1D—C1D—N2D | 173.9 (5) |
C4B—S1BA—C2B | 106.3 (6) | C2D—S1DA—C4D | 106.9 (6) |
C2B—S2BA—C3B | 105.2 (6) | C2D—S2DA—C3D | 107.6 (6) |
C2B—N2BA—C1BA | 110 (4) | C2D—N2DA—C1DA | 111 (4) |
N1B—C1BA—N2BA | 177 (5) | N1D—C1DA—N2DA | 159 (6) |
N2BA—C2B—S2BA | 127.7 (19) | N2DA—C2D—S2DA | 123.3 (16) |
N2B—C2B—S1B | 120.0 (3) | N2D—C2D—S1D | 120.5 (3) |
N2B—C2B—S2B | 122.4 (3) | N2D—C2D—S2D | 120.6 (3) |
S1B—C2B—S2B | 117.6 (2) | S1D—C2D—S2D | 118.9 (2) |
N2BA—C2B—S1BA | 108.7 (19) | N2DA—C2D—S1DA | 114.0 (16) |
S2BA—C2B—S1BA | 123.4 (6) | S2DA—C2D—S1DA | 122.0 (5) |
S1B—C3B—H3BA | 109.5 | S1D—C3D—H3DA | 109.5 |
S1B—C3B—H3BB | 109.5 | S1D—C3D—H3DB | 109.5 |
H3BA—C3B—H3BB | 109.5 | H3DA—C3D—H3DB | 109.5 |
S1B—C3B—H3BC | 109.5 | S1D—C3D—H3DC | 109.5 |
H3BA—C3B—H3BC | 109.5 | H3DA—C3D—H3DC | 109.5 |
H3BB—C3B—H3BC | 109.5 | H3DB—C3D—H3DC | 109.5 |
S2BA—C3B—H3BD | 109.5 | S2DA—C3D—H3DD | 109.5 |
S2BA—C3B—H3BE | 109.5 | S2DA—C3D—H3DE | 109.5 |
H3BD—C3B—H3BE | 109.5 | H3DD—C3D—H3DE | 109.5 |
S2BA—C3B—H3BF | 109.5 | S2DA—C3D—H3DF | 109.5 |
H3BD—C3B—H3BF | 109.5 | H3DD—C3D—H3DF | 109.5 |
H3BE—C3B—H3BF | 109.5 | H3DE—C3D—H3DF | 109.5 |
S2B—C4B—H4BA | 109.5 | S2D—C4D—H4DA | 109.5 |
S2B—C4B—H4BB | 109.5 | S2D—C4D—H4DB | 109.5 |
H4BA—C4B—H4BB | 109.5 | H4DA—C4D—H4DB | 109.5 |
S2B—C4B—H4BC | 109.5 | S2D—C4D—H4DC | 109.5 |
H4BA—C4B—H4BC | 109.5 | H4DA—C4D—H4DC | 109.5 |
H4BB—C4B—H4BC | 109.5 | H4DB—C4D—H4DC | 109.5 |
S1BA—C4B—H4BD | 109.5 | S1DA—C4D—H4DD | 109.5 |
S1BA—C4B—H4BE | 109.5 | S1DA—C4D—H4DE | 109.5 |
H4BD—C4B—H4BE | 109.5 | H4DD—C4D—H4DE | 109.5 |
S1BA—C4B—H4BF | 109.5 | S1DA—C4D—H4DF | 109.5 |
H4BD—C4B—H4BF | 109.5 | H4DD—C4D—H4DF | 109.5 |
H4BE—C4B—H4BF | 109.5 | H4DE—C4D—H4DF | 109.5 |
C1A—N2A—C2A—S1A | −179.2 (3) | C1C—N2C—C2C—S2C | 0.9 (5) |
C1A—N2A—C2A—S2A | −0.4 (5) | C3C—S1C—C2C—N2C | 0.1 (4) |
C3A—S1A—C2A—N2A | 0.0 (4) | C3C—S1C—C2C—S2C | 178.9 (2) |
C3A—S1A—C2A—S2A | −178.8 (2) | C4C—S2C—C2C—N2C | −177.5 (3) |
C4A—S2A—C2A—N2A | 175.8 (3) | C4C—S2C—C2C—S1C | 3.8 (3) |
C4A—S2A—C2A—S1A | −5.4 (3) | C2D—N2DA—C1DA—N1D | 149 (15) |
C1B—N2B—C2B—S1B | −179.4 (3) | C1D—N2D—C2D—S1D | −176.5 (4) |
C1B—N2B—C2B—S2B | −0.5 (5) | C1D—N2D—C2D—S2D | 2.6 (5) |
C1BA—N2BA—C2B—S2BA | −5 (4) | C1DA—N2DA—C2D—S2DA | −11 (4) |
C1BA—N2BA—C2B—S1BA | 180 (3) | C1DA—N2DA—C2D—S1DA | 179 (3) |
C3B—S2BA—C2B—N2BA | −176 (2) | C3D—S2DA—C2D—N2DA | −176.0 (17) |
C3B—S2BA—C2B—S1BA | −0.5 (9) | C3D—S2DA—C2D—S1DA | −6.8 (8) |
C3B—S1B—C2B—N2B | 0.6 (4) | C3D—S1D—C2D—N2D | −3.6 (4) |
C3B—S1B—C2B—S2B | −178.4 (2) | C3D—S1D—C2D—S2D | 177.4 (2) |
C4B—S2B—C2B—N2B | 179.9 (3) | C4D—S2D—C2D—N2D | −178.8 (3) |
C4B—S2B—C2B—S1B | −1.2 (3) | C4D—S2D—C2D—S1D | 0.2 (3) |
C4B—S1BA—C2B—N2BA | −9.0 (18) | C4D—S1DA—C2D—N2DA | −17.2 (17) |
C4B—S1BA—C2B—S2BA | 175.0 (5) | C4D—S1DA—C2D—S2DA | 172.6 (6) |
C1C—N2C—C2C—S1C | 179.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4B—H4BB···N1Bi | 0.98 | 2.56 | 3.424 (5) | 147 |
C3D—H3DB···N1Cii | 0.98 | 2.59 | 3.460 (5) | 149 |
C4D—H4DA···N1Biii | 0.98 | 2.52 | 3.485 (6) | 166 |
Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) −x+2, −y, −z+1; (iii) x+1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C4B—H4BB···N1Bi | 0.98 | 2.56 | 3.424 (5) | 147 |
C3D—H3DB···N1Cii | 0.98 | 2.59 | 3.460 (5) | 149 |
C4D—H4DA···N1Biii | 0.98 | 2.52 | 3.485 (6) | 166 |
Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) −x+2, −y, −z+1; (iii) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C4H6N2S2 |
Mr | 146.23 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 120 |
a, b, c (Å) | 15.2211 (18), 12.2037 (15), 14.4716 (18) |
β (°) | 98.788 (5) |
V (Å3) | 2656.6 (6) |
Z | 16 |
Radiation type | Mo Kα |
µ (mm−1) | 0.69 |
Crystal size (mm) | 0.19 × 0.12 × 0.04 |
Data collection | |
Diffractometer | Bruker Kappa X8 APEXIII |
Absorption correction | Multi-scan (SADABS; Krause et al., 2015) |
Tmin, Tmax | 0.837, 0.983 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 36932, 4868, 2986 |
Rint | 0.105 |
(sin θ/λ)max (Å−1) | 0.602 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.106, 1.07 |
No. of reflections | 4868 |
No. of parameters | 331 |
No. of restraints | 24 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.86, −0.37 |
Computer programs: APEX3 (Bruker, 2015), SAINT (Bruker, 2015), SHELXT (Sheldrick, 2015a), PLATON (Spek, 2009), SHELXL2014 (Sheldrick, 2015b) and publCIF (Westrip, 2010).
Acknowledgements
The authors acknowledge the Cheikh Anta Diop University of Dakar (Senegal) and the University of Notre Dame (USA) for financial support.
References
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