Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807028280/ez2082sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807028280/ez2082Isup2.hkl |
CCDC reference: 654951
Freshly prepared pivaloylisothiocyanate (1.43 g, 10 mmol) was stirred in acetone (30 ml) for 15 minutes. Neat 3-chloroaniline (1.3 g, 10 mmol) was then added and the resulting mixture was stirred for 1 h. The reaction mixture was then poured into acidified (pH 4) water and stirred well. The solid product was separated and washed with deionized water and purified by recrystallization from methanol/ 1,1-dichloromethane (1:10 v/v) to give fine crystals of (I), with an overall yield of 85%.
Hydrogen atoms bonded to C were included in calculated positions and refined as riding on their parent C atom with C—H = 0.95 Å Uiso(H) = 1.2Ueq(C) or C—H = 0.98 Å and Uiso(H) = 1.5Ueq(C), respectively, for aromatic and methyl C atoms. The H atoms bonded to N were freely refined. The tert-butyl group is disordered over two positions with site occupation factors of 0.50 (1)/0.50 (1). The C—C distances and C—C—C angles of the tert-butyl groups were restrained to be equal.
The background to this study has been set out in our previous work on the structural chemistry of N,N'-disubstituted thioureas (Shoukat et al., 2007). Herein, as a continuation of these studies, the structure of the title compound (I) is described. A depiction of the molecule is given in Fig. 1. Bond lengths and angles, see the table of selected geometric parameters, can be regarded as typical for N,N'-disubstituted thiourea compounds as found in the Cambridge Structural Database v5.28 (Allen, 2002; Khawar Rauf et al., 2006). The molecule exists in the thione form with typical thiourea C—S and C—O bonds, as well as shortened C—N bond lengths. The thiocarbonyl and carbonyl groups are almost coplanar (see selected geometric parameters table). The molecule features an intramolecular N—H···O hydrogen bond and in the crystal structure, molecules associate via N—H···S intermolecular hydrogen bonds to form a chain (see the table of hydrogen bond geometries; Fig 2).
For related literature, see: Shoukat et al. (2007); Khawar Rauf et al. (2006); Allen (2002).
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97.
C12H15ClN2OS | F(000) = 568 |
Mr = 270.77 | Dx = 1.350 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 34614 reflections |
a = 6.1269 (2) Å | θ = 3.5–29.8° |
b = 10.2848 (4) Å | µ = 0.43 mm−1 |
c = 21.1360 (9) Å | T = 173 K |
V = 1331.86 (9) Å3 | Block, colourless |
Z = 4 | 0.49 × 0.49 × 0.47 mm |
Stoe IPDSII two-circle diffractometer | 3742 independent reflections |
Radiation source: fine-focus sealed tube | 3700 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
ω scans | θmax = 29.6°, θmin = 3.5° |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | h = −8→8 |
Tmin = 0.817, Tmax = 0.824 | k = −14→14 |
35409 measured reflections | l = −29→29 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.023 | w = 1/[σ2(Fo2) + (0.0361P)2 + 0.1922P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.062 | (Δ/σ)max = 0.002 |
S = 1.04 | Δρmax = 0.22 e Å−3 |
3742 reflections | Δρmin = −0.18 e Å−3 |
191 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
30 restraints | Extinction coefficient: 0.028 (2) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack, (1983), 1573 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.01 (4) |
C12H15ClN2OS | V = 1331.86 (9) Å3 |
Mr = 270.77 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 6.1269 (2) Å | µ = 0.43 mm−1 |
b = 10.2848 (4) Å | T = 173 K |
c = 21.1360 (9) Å | 0.49 × 0.49 × 0.47 mm |
Stoe IPDSII two-circle diffractometer | 3742 independent reflections |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | 3700 reflections with I > 2σ(I) |
Tmin = 0.817, Tmax = 0.824 | Rint = 0.052 |
35409 measured reflections |
R[F2 > 2σ(F2)] = 0.023 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.062 | Δρmax = 0.22 e Å−3 |
S = 1.04 | Δρmin = −0.18 e Å−3 |
3742 reflections | Absolute structure: Flack, (1983), 1573 Friedel pairs |
191 parameters | Absolute structure parameter: −0.01 (4) |
30 restraints |
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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Cl1 | 0.56583 (5) | 0.11877 (3) | 0.622329 (14) | 0.03278 (8) | |
S1 | 0.71872 (4) | 0.66862 (3) | 0.541901 (12) | 0.02455 (7) | |
O1 | 0.53343 (17) | 0.53031 (9) | 0.34538 (4) | 0.0357 (2) | |
N1 | 0.51185 (16) | 0.50045 (9) | 0.46671 (4) | 0.02377 (17) | |
H1 | 0.471 (3) | 0.4776 (19) | 0.4264 (9) | 0.052 (5)* | |
N2 | 0.72061 (15) | 0.65585 (8) | 0.41596 (4) | 0.02134 (16) | |
H2 | 0.821 (3) | 0.7168 (17) | 0.4228 (8) | 0.040 (4)* | |
C1 | 0.64372 (15) | 0.60313 (9) | 0.47266 (5) | 0.01990 (17) | |
C2 | 0.66320 (17) | 0.61904 (11) | 0.35498 (5) | 0.02307 (19) | |
C3 | 0.76111 (18) | 0.69697 (11) | 0.30021 (5) | 0.0255 (2) | |
C11 | 0.41745 (17) | 0.43202 (9) | 0.51909 (5) | 0.02176 (18) | |
C12 | 0.52851 (16) | 0.32519 (10) | 0.54368 (5) | 0.02213 (18) | |
H12 | 0.6688 | 0.3019 | 0.5283 | 0.027* | |
C13 | 0.42847 (18) | 0.25339 (10) | 0.59147 (5) | 0.02302 (19) | |
C14 | 0.2224 (2) | 0.28558 (11) | 0.61466 (5) | 0.0260 (2) | |
H14 | 0.1563 | 0.2352 | 0.6471 | 0.031* | |
C15 | 0.11545 (18) | 0.39324 (12) | 0.58923 (5) | 0.0283 (2) | |
H15 | −0.0247 | 0.4166 | 0.6047 | 0.034* | |
C16 | 0.21162 (18) | 0.46708 (10) | 0.54130 (5) | 0.02590 (19) | |
H16 | 0.1377 | 0.5402 | 0.5241 | 0.031* | |
C31 | 0.6919 (19) | 0.8377 (6) | 0.3090 (4) | 0.075 (3) | 0.501 (14) |
H31A | 0.7498 | 0.8706 | 0.3492 | 0.112* | 0.501 (14) |
H31B | 0.5322 | 0.8431 | 0.3095 | 0.112* | 0.501 (14) |
H31C | 0.7491 | 0.8903 | 0.2741 | 0.112* | 0.501 (14) |
C32 | 0.6826 (14) | 0.6375 (10) | 0.2402 (3) | 0.072 (3) | 0.501 (14) |
H32A | 0.7430 | 0.6855 | 0.2041 | 0.108* | 0.501 (14) |
H32B | 0.5229 | 0.6411 | 0.2387 | 0.108* | 0.501 (14) |
H32C | 0.7303 | 0.5466 | 0.2381 | 0.108* | 0.501 (14) |
C33 | 1.0128 (9) | 0.6913 (7) | 0.3023 (3) | 0.0448 (12) | 0.501 (14) |
H33A | 1.0646 | 0.7296 | 0.3420 | 0.067* | 0.501 (14) |
H33B | 1.0729 | 0.7401 | 0.2665 | 0.067* | 0.501 (14) |
H33C | 1.0606 | 0.6005 | 0.2998 | 0.067* | 0.501 (14) |
C31' | 0.6110 (11) | 0.8150 (7) | 0.2875 (3) | 0.0556 (14) | 0.499 (14) |
H31D | 0.4607 | 0.7849 | 0.2814 | 0.083* | 0.499 (14) |
H31E | 0.6605 | 0.8604 | 0.2493 | 0.083* | 0.499 (14) |
H31F | 0.6168 | 0.8746 | 0.3236 | 0.083* | 0.499 (14) |
C32' | 0.7525 (16) | 0.6115 (6) | 0.2407 (3) | 0.058 (2) | 0.499 (14) |
H32D | 0.6026 | 0.5814 | 0.2338 | 0.087* | 0.499 (14) |
H32E | 0.8488 | 0.5363 | 0.2462 | 0.087* | 0.499 (14) |
H32F | 0.8007 | 0.6622 | 0.2040 | 0.087* | 0.499 (14) |
C33' | 0.9919 (10) | 0.7433 (11) | 0.3097 (3) | 0.0562 (19) | 0.499 (14) |
H33D | 1.0396 | 0.7918 | 0.2722 | 0.084* | 0.499 (14) |
H33E | 1.0880 | 0.6682 | 0.3161 | 0.084* | 0.499 (14) |
H33F | 0.9985 | 0.7999 | 0.3469 | 0.084* | 0.499 (14) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.04062 (15) | 0.02760 (12) | 0.03014 (13) | 0.00457 (11) | −0.00164 (11) | 0.00577 (10) |
S1 | 0.02621 (11) | 0.02688 (12) | 0.02055 (11) | −0.00204 (9) | −0.00021 (9) | −0.00280 (9) |
O1 | 0.0454 (5) | 0.0378 (5) | 0.0238 (4) | −0.0202 (4) | −0.0028 (4) | 0.0016 (3) |
N1 | 0.0308 (4) | 0.0221 (4) | 0.0184 (4) | −0.0057 (3) | 0.0028 (3) | −0.0004 (3) |
N2 | 0.0240 (4) | 0.0209 (3) | 0.0191 (4) | −0.0036 (3) | 0.0014 (3) | 0.0001 (3) |
C1 | 0.0200 (4) | 0.0185 (4) | 0.0212 (4) | 0.0025 (3) | 0.0025 (3) | 0.0009 (3) |
C2 | 0.0266 (4) | 0.0229 (4) | 0.0197 (4) | −0.0017 (4) | 0.0002 (3) | 0.0014 (4) |
C3 | 0.0312 (5) | 0.0255 (4) | 0.0198 (4) | −0.0044 (4) | 0.0005 (4) | 0.0033 (4) |
C11 | 0.0247 (4) | 0.0215 (4) | 0.0190 (4) | −0.0034 (4) | 0.0031 (4) | −0.0006 (3) |
C12 | 0.0220 (4) | 0.0238 (4) | 0.0207 (4) | −0.0019 (3) | 0.0014 (3) | −0.0013 (4) |
C13 | 0.0274 (5) | 0.0214 (4) | 0.0203 (4) | −0.0014 (4) | −0.0018 (4) | 0.0002 (3) |
C14 | 0.0296 (5) | 0.0278 (5) | 0.0205 (4) | −0.0051 (4) | 0.0051 (4) | 0.0003 (4) |
C15 | 0.0261 (5) | 0.0324 (5) | 0.0264 (5) | 0.0012 (4) | 0.0074 (4) | −0.0012 (4) |
C16 | 0.0276 (4) | 0.0254 (4) | 0.0247 (5) | 0.0029 (4) | 0.0025 (4) | 0.0006 (4) |
C31 | 0.118 (6) | 0.039 (2) | 0.068 (4) | 0.031 (3) | 0.045 (4) | 0.032 (2) |
C32 | 0.077 (4) | 0.120 (6) | 0.019 (2) | −0.063 (4) | −0.013 (2) | 0.018 (3) |
C33 | 0.0357 (15) | 0.060 (3) | 0.0384 (19) | −0.0093 (19) | 0.0065 (13) | 0.016 (2) |
C31' | 0.067 (3) | 0.052 (3) | 0.048 (3) | 0.025 (2) | 0.018 (2) | 0.027 (2) |
C32' | 0.106 (6) | 0.0388 (18) | 0.029 (2) | −0.036 (3) | 0.022 (3) | −0.0107 (15) |
C33' | 0.043 (2) | 0.092 (5) | 0.034 (2) | −0.034 (3) | −0.0109 (18) | 0.030 (3) |
Cl1—C13 | 1.7466 (11) | C14—H14 | 0.9500 |
S1—C1 | 1.6753 (10) | C15—C16 | 1.3965 (15) |
O1—C2 | 1.2272 (13) | C15—H15 | 0.9500 |
N1—C1 | 1.3356 (13) | C16—H16 | 0.9500 |
N1—C11 | 1.4337 (13) | C31—H31A | 0.9800 |
N1—H1 | 0.918 (19) | C31—H31B | 0.9800 |
N2—C2 | 1.3887 (13) | C31—H31C | 0.9800 |
N2—C1 | 1.3972 (12) | C32—H32A | 0.9800 |
N2—H2 | 0.889 (18) | C32—H32B | 0.9800 |
C2—C3 | 1.5304 (14) | C32—H32C | 0.9800 |
C3—C32 | 1.489 (6) | C33—H33A | 0.9800 |
C3—C33' | 1.506 (5) | C33—H33B | 0.9800 |
C3—C31 | 1.520 (5) | C33—H33C | 0.9800 |
C3—C32' | 1.536 (5) | C31'—H31D | 0.9800 |
C3—C33 | 1.544 (5) | C31'—H31E | 0.9800 |
C3—C31' | 1.547 (5) | C31'—H31F | 0.9800 |
C11—C16 | 1.3931 (14) | C32'—H32D | 0.9800 |
C11—C12 | 1.3930 (14) | C32'—H32E | 0.9800 |
C12—C13 | 1.3932 (14) | C32'—H32F | 0.9800 |
C12—H12 | 0.9500 | C33'—H33D | 0.9800 |
C13—C14 | 1.3940 (16) | C33'—H33E | 0.9800 |
C14—C15 | 1.3945 (16) | C33'—H33F | 0.9800 |
C1—N1—C11 | 124.02 (9) | C11—C16—C15 | 119.05 (10) |
C1—N1—H1 | 117.0 (12) | C11—C16—H16 | 120.5 |
C11—N1—H1 | 118.8 (13) | C15—C16—H16 | 120.5 |
C2—N2—C1 | 127.23 (9) | C3—C31—H31A | 109.5 |
C2—N2—H2 | 121.2 (11) | C3—C31—H31B | 109.5 |
C1—N2—H2 | 111.5 (11) | H31A—C31—H31B | 109.5 |
N1—C1—N2 | 115.47 (9) | C3—C31—H31C | 109.5 |
N1—C1—S1 | 124.48 (8) | H31A—C31—H31C | 109.5 |
N2—C1—S1 | 120.05 (7) | H31B—C31—H31C | 109.5 |
O1—C2—N2 | 121.35 (9) | C3—C32—H32A | 109.5 |
O1—C2—C3 | 121.22 (9) | C3—C32—H32B | 109.5 |
N2—C2—C3 | 117.39 (9) | H32A—C32—H32B | 109.5 |
C32—C3—C31 | 114.0 (4) | C3—C32—H32C | 109.5 |
C32—C3—C2 | 107.6 (3) | H32A—C32—H32C | 109.5 |
C33'—C3—C2 | 115.7 (2) | H32B—C32—H32C | 109.5 |
C31—C3—C2 | 107.3 (2) | C3—C33—H33A | 109.5 |
C32—C3—C32' | 19.1 (5) | C3—C33—H33B | 109.5 |
C33'—C3—C32' | 108.8 (4) | H33A—C33—H33B | 109.5 |
C2—C3—C32' | 107.8 (3) | C3—C33—H33C | 109.5 |
C32—C3—C33 | 109.4 (4) | H33A—C33—H33C | 109.5 |
C31—C3—C33 | 108.1 (4) | H33B—C33—H33C | 109.5 |
C2—C3—C33 | 110.5 (3) | C3—C31'—H31D | 109.5 |
C33'—C3—C31' | 109.5 (4) | C3—C31'—H31E | 109.5 |
C2—C3—C31' | 108.0 (2) | H31D—C31'—H31E | 109.5 |
C32'—C3—C31' | 106.6 (3) | C3—C31'—H31F | 109.5 |
C16—C11—C12 | 121.37 (9) | H31D—C31'—H31F | 109.5 |
C16—C11—N1 | 119.89 (9) | H31E—C31'—H31F | 109.5 |
C12—C11—N1 | 118.57 (9) | C3—C32'—H32D | 109.5 |
C11—C12—C13 | 118.27 (9) | C3—C32'—H32E | 109.5 |
C11—C12—H12 | 120.9 | H32D—C32'—H32E | 109.5 |
C13—C12—H12 | 120.9 | C3—C32'—H32F | 109.5 |
C12—C13—C14 | 121.83 (10) | H32D—C32'—H32F | 109.5 |
C12—C13—Cl1 | 118.61 (8) | H32E—C32'—H32F | 109.5 |
C14—C13—Cl1 | 119.56 (8) | C3—C33'—H33D | 109.5 |
C13—C14—C15 | 118.60 (10) | C3—C33'—H33E | 109.5 |
C13—C14—H14 | 120.7 | H33D—C33'—H33E | 109.5 |
C15—C14—H14 | 120.7 | C3—C33'—H33F | 109.5 |
C14—C15—C16 | 120.87 (10) | H33D—C33'—H33F | 109.5 |
C14—C15—H15 | 119.6 | H33E—C33'—H33F | 109.5 |
C16—C15—H15 | 119.6 | ||
C11—N1—C1—N2 | 179.50 (9) | N2—C2—C3—C33 | 58.8 (3) |
C11—N1—C1—S1 | −0.31 (15) | O1—C2—C3—C31' | 90.7 (4) |
C2—N2—C1—N1 | 4.83 (15) | N2—C2—C3—C31' | −87.0 (4) |
C2—N2—C1—S1 | −175.35 (8) | C1—N1—C11—C16 | 92.59 (13) |
C1—N2—C2—O1 | −0.89 (17) | C1—N1—C11—C12 | −92.01 (13) |
C1—N2—C2—C3 | 176.75 (9) | C16—C11—C12—C13 | −0.02 (15) |
O1—C2—C3—C32 | −4.2 (5) | N1—C11—C12—C13 | −175.36 (9) |
N2—C2—C3—C32 | 178.2 (5) | C11—C12—C13—C14 | 0.19 (15) |
O1—C2—C3—C33' | −146.3 (5) | C11—C12—C13—Cl1 | 179.68 (7) |
N2—C2—C3—C33' | 36.1 (5) | C12—C13—C14—C15 | −0.34 (16) |
O1—C2—C3—C31 | 118.8 (6) | Cl1—C13—C14—C15 | −179.83 (9) |
N2—C2—C3—C31 | −58.8 (6) | C13—C14—C15—C16 | 0.33 (17) |
O1—C2—C3—C32' | −24.3 (4) | C12—C11—C16—C15 | 0.02 (16) |
N2—C2—C3—C32' | 158.1 (4) | N1—C11—C16—C15 | 175.29 (10) |
O1—C2—C3—C33 | −123.5 (3) | C14—C15—C16—C11 | −0.18 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.918 (19) | 1.836 (19) | 2.5863 (12) | 137.2 (18) |
N2—H2···S1i | 0.889 (18) | 2.808 (18) | 3.6560 (9) | 159.8 (14) |
Symmetry code: (i) x+1/2, −y+3/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C12H15ClN2OS |
Mr | 270.77 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 173 |
a, b, c (Å) | 6.1269 (2), 10.2848 (4), 21.1360 (9) |
V (Å3) | 1331.86 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.43 |
Crystal size (mm) | 0.49 × 0.49 × 0.47 |
Data collection | |
Diffractometer | Stoe IPDSII two-circle |
Absorption correction | Multi-scan (MULABS; Spek, 2003; Blessing, 1995) |
Tmin, Tmax | 0.817, 0.824 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 35409, 3742, 3700 |
Rint | 0.052 |
(sin θ/λ)max (Å−1) | 0.695 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.023, 0.062, 1.04 |
No. of reflections | 3742 |
No. of parameters | 191 |
No. of restraints | 30 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.22, −0.18 |
Absolute structure | Flack, (1983), 1573 Friedel pairs |
Absolute structure parameter | −0.01 (4) |
Computer programs: X-AREA (Stoe & Cie, 2001), X-AREA, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP in SHELXTL-Plus (Sheldrick, 1991), SHELXL97.
S1—C1 | 1.6753 (10) | N1—C11 | 1.4337 (13) |
O1—C2 | 1.2272 (13) | N2—C2 | 1.3887 (13) |
N1—C1 | 1.3356 (13) | N2—C1 | 1.3972 (12) |
C2—N2—C1—N1 | 4.83 (15) | C1—N2—C2—O1 | −0.89 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.918 (19) | 1.836 (19) | 2.5863 (12) | 137.2 (18) |
N2—H2···S1i | 0.889 (18) | 2.808 (18) | 3.6560 (9) | 159.8 (14) |
Symmetry code: (i) x+1/2, −y+3/2, −z+1. |
The background to this study has been set out in our previous work on the structural chemistry of N,N'-disubstituted thioureas (Shoukat et al., 2007). Herein, as a continuation of these studies, the structure of the title compound (I) is described. A depiction of the molecule is given in Fig. 1. Bond lengths and angles, see the table of selected geometric parameters, can be regarded as typical for N,N'-disubstituted thiourea compounds as found in the Cambridge Structural Database v5.28 (Allen, 2002; Khawar Rauf et al., 2006). The molecule exists in the thione form with typical thiourea C—S and C—O bonds, as well as shortened C—N bond lengths. The thiocarbonyl and carbonyl groups are almost coplanar (see selected geometric parameters table). The molecule features an intramolecular N—H···O hydrogen bond and in the crystal structure, molecules associate via N—H···S intermolecular hydrogen bonds to form a chain (see the table of hydrogen bond geometries; Fig 2).