O-Propyl N-phenyl­thio­carbamate

Sudkaow, P.; Yeo, C.I.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S160053681202140X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1774

doi:10.1107/S160053681202140X

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O-Propyl N-phenylthiocarbamate

Panyapon Sudkaow,^a,^b Chien Ing Yeo,^a Seik Weng Ng ^a,^c and Edward R. T. Tiekink ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, ^bDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Thailand 90110, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 11 May 2012; accepted 11 May 2012; online 19 May 2012)

Two independent molecules comprise the asymmetric unit in the title thiocarbamide derivative, C₁₀H₁₃NOS. These differ in the relative orientations of terminal ethyl groups [C—C—C—O torsion angles = −66.95 (13) and 55.92 (13)°, respectively]. The phenyl ring is twisted out of the plane of the central residue [C_q—N—C_ph—C_ph = −146.20 (12) and −144.15 (12)°, respectively; q = quaternary and ph = phenyl]. The independent molecules are linked into a dimeric aggregate by N—H⋯S hydrogen bonds and an eight-membered thioamide {⋯H—N—C=S}₂ synthon.

Related literature

For related thiocarbamaide structures, see: Ho et al. (2005 ); Kuan et al. (2007 ).

Experimental

Crystal data

C₁₀H₁₃NOS
M_r = 195.27
Triclinic, $[P \overline 1]$
a = 8.9230 (4) Å
b = 9.8752 (4) Å
c = 12.9613 (5) Å
α = 98.037 (3)°
β = 105.866 (4)°
γ = 104.533 (4)°
V = 1036.46 (7) Å³
Z = 4
Cu Kα radiation
μ = 2.45 mm⁻¹
T = 100 K
0.35 × 0.30 × 0.25 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.772, T_max = 1.000
7531 measured reflections
4249 independent reflections
4049 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.081
S = 1.04
4249 reflections
243 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯S2	0.88 (1)	2.51 (1)	3.3667 (10)	164 (2)
N2—H2n⋯S1	0.88 (1)	2.52 (1)	3.3765 (10)	167 (2)

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ), DIAMOND (Brandenburg, 2006 ) and QMol (Gans & Shalloway, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681202140X/hg5228sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681202140X/hg5228Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681202140X/hg5228Isup3.cml

checkCIF report

Comment top

The title thiocarbamate, (I), was investigated as a continuation of systematic evaluation of the structural features of this class of compound (Ho et al., 2005; Kuan et al., 2007). In (I), Fig. 1, two independent molecules comprise the asymmetric unit, and these have very similar molecular conformations as seen in the overlay diagram, Fig. 2. The difference arises in the pseudo mirror relationship in the terminal ethyl group as seen in the C1—C2—C3—O1 and C11—C12—C13—O2 torsion angles of -66.95 (13) and 55.92 (13)°, respectively. A further twist is evident in the molecule as seen in the value of the C4—N1—C5—C6 torsion angle of -146.20 (12)°; the equivalent torsion angle for the second independent molecule [C14—N2—C15—C16] is -144.15 (12)°. The geometric parameters match literature precedents (Ho et al., 2005; Kuan et al., 2007)

The independent molecules are linked into a dimeric aggregate by N—H···S hydrogen bonds and an eight-membered thioamide {···H—N—C=S}₂ synthon, Table 1, as found in most thiocarbamate structures (Kuan et al., 2007). Molecules assemble into a three-dimensional architecture with no specific interactions between them.

Related literature top

For related thiocarbamaide structures, see: Ho et al. (2005); Kuan et al. (2007).

Experimental top

Phenyl isothiocyanate (2 ml) was added drop-wise to a stirred solution of NaOH (1 mol equiv.) in n-propanol (20 ml) and stirred for 3 h. Excess HCl (5M) was then added and the solution was stirred for a further 1 h. The product was then extracted with CHCl₃ and left for evaporation at room temperature, yielding colourless crystals after 2 weeks. IR (KBr, cm^-1): ν(N—H) 3211 (br); ν(C—N) 1410 (s); ν(C═S) 1221 (s); ν(C—O) 1060 (s). ¹H NMR (CDCl₃, p.p.m.): δ 1.00 (t, J = 7.44 Hz, 3H, CH₃), 1.80 (sextet, J = 7.06 Hz, 2H, CH₂), 4.54 (br, 2H, CH₂O), 7.16 – 7.35 (br, m, 5H aryl-H), 8.85 (br, 1H NH). M.pt: 311–312 K.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006) and QMol (Gans & Shalloway, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structures of the two independent molecules comprising (I) showing the atom-labelling scheme and displacement ellipsoids at the 70% probability level. The dashed lines represent N—H hydrogen bonds.
	Fig. 2. Overlay diagram of the two independent molecules comprising the asymmetric unit of (I). The first independent molecule (with the S1 atom) is shown in red and the second (S2) in blue. The S, O and N atoms in each molecule have been overlapped.

O-Propyl N-phenylthiocarbamate top

Crystal data top

C₁₀H₁₃NOS	Z = 4
M_r = 195.27	F(000) = 416
Triclinic, P1	D_x = 1.251 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 8.9230 (4) Å	Cell parameters from 5287 reflections
b = 9.8752 (4) Å	θ = 4.7–76.4°
c = 12.9613 (5) Å	µ = 2.45 mm⁻¹
α = 98.037 (3)°	T = 100 K
β = 105.866 (4)°	Prism, colourless
γ = 104.533 (4)°	0.35 × 0.30 × 0.25 mm
V = 1036.46 (7) Å³

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4249 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	4049 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.014
Detector resolution: 10.4041 pixels mm^-1	θ_max = 76.6°, θ_min = 4.8°
ω scan	h = −7→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −11→12
T_min = 0.772, T_max = 1.000	l = −15→16
7531 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0468P)² + 0.325P] where P = (F_o² + 2F_c²)/3
4249 reflections	(Δ/σ)_max = 0.001
243 parameters	Δρ_max = 0.22 e Å⁻³
2 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₀H₁₃NOS	γ = 104.533 (4)°
M_r = 195.27	V = 1036.46 (7) Å³
Triclinic, P1	Z = 4
a = 8.9230 (4) Å	Cu Kα radiation
b = 9.8752 (4) Å	µ = 2.45 mm⁻¹
c = 12.9613 (5) Å	T = 100 K
α = 98.037 (3)°	0.35 × 0.30 × 0.25 mm
β = 105.866 (4)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4249 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	4049 reflections with I > 2σ(I)
T_min = 0.772, T_max = 1.000	R_int = 0.014
7531 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	2 restraints
wR(F²) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.22 e Å⁻³
4249 reflections	Δρ_min = −0.26 e Å⁻³
243 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.

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.

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

	x	y	z	U_iso*/U_eq
S1	0.71820 (3)	0.96137 (3)	0.53434 (2)	0.01838 (9)
S2	0.28880 (3)	0.57145 (3)	0.43767 (2)	0.01822 (9)
O1	0.69183 (10)	1.01848 (8)	0.33618 (6)	0.01621 (17)
O2	0.32823 (10)	0.50276 (9)	0.63279 (7)	0.01760 (18)
N1	0.50067 (12)	0.82607 (11)	0.33959 (8)	0.0170 (2)
N2	0.51265 (12)	0.70040 (10)	0.63170 (8)	0.0163 (2)
C1	0.92887 (18)	1.12337 (16)	0.22198 (11)	0.0293 (3)
H1A	0.9495	1.1744	0.1652	0.044*
H1B	0.8424	1.0319	0.1872	0.044*
H1C	1.0292	1.1051	0.2626	0.044*
C2	0.87524 (15)	1.21464 (13)	0.30110 (10)	0.0208 (2)
H2A	0.9631	1.3068	0.3359	0.025*
H2B	0.7769	1.2364	0.2590	0.025*
C3	0.83708 (14)	1.14212 (12)	0.38999 (10)	0.0178 (2)
H3A	0.9302	1.1107	0.4283	0.021*
H3B	0.8161	1.2092	0.4447	0.021*
C4	0.63469 (13)	0.93553 (12)	0.39794 (9)	0.0152 (2)
C5	0.41567 (14)	0.78782 (12)	0.22442 (9)	0.0152 (2)
C6	0.24671 (14)	0.72731 (12)	0.19297 (10)	0.0176 (2)
H6	0.1942	0.7184	0.2474	0.021*
C7	0.15509 (14)	0.68008 (13)	0.08232 (10)	0.0199 (2)
H7	0.0400	0.6378	0.0612	0.024*
C8	0.23078 (15)	0.69437 (13)	0.00225 (10)	0.0203 (2)
H8	0.1678	0.6631	−0.0735	0.024*
C9	0.39904 (15)	0.75463 (14)	0.03377 (10)	0.0219 (2)
H9	0.4511	0.7642	−0.0209	0.026*
C10	0.49257 (14)	0.80118 (13)	0.14456 (10)	0.0197 (2)
H10	0.6079	0.8417	0.1655	0.024*
C11	0.15346 (15)	0.40071 (14)	0.77344 (10)	0.0239 (3)
H11A	0.1401	0.3434	0.8281	0.036*
H11B	0.0630	0.4418	0.7546	0.036*
H11C	0.2573	0.4782	0.8040	0.036*
C12	0.15342 (15)	0.30544 (13)	0.67048 (10)	0.0197 (2)
H12A	0.2421	0.2610	0.6908	0.024*
H12B	0.0484	0.2272	0.6404	0.024*
C13	0.17672 (14)	0.38556 (12)	0.58226 (9)	0.0184 (2)
H13A	0.1841	0.3213	0.5192	0.022*
H13B	0.0838	0.4233	0.5555	0.022*
C14	0.38000 (14)	0.59088 (12)	0.57262 (9)	0.0152 (2)
C15	0.60105 (13)	0.72986 (12)	0.74636 (9)	0.0151 (2)
C16	0.66568 (14)	0.87358 (12)	0.80113 (10)	0.0183 (2)
H16	0.6453	0.9459	0.7630	0.022*
C17	0.76006 (15)	0.91136 (13)	0.91153 (10)	0.0203 (2)
H17	0.8049	1.0096	0.9487	0.024*
C18	0.78895 (14)	0.80571 (13)	0.96760 (10)	0.0204 (2)
H18	0.8531	0.8313	1.0432	0.025*
C19	0.72344 (14)	0.66214 (13)	0.91244 (10)	0.0201 (2)
H19	0.7424	0.5898	0.9509	0.024*
C20	0.63053 (14)	0.62339 (12)	0.80164 (10)	0.0180 (2)
H20	0.5877	0.5253	0.7641	0.022*
H1n	0.452 (2)	0.7739 (17)	0.3777 (13)	0.033 (4)*
H2n	0.5510 (19)	0.7633 (15)	0.5966 (12)	0.029 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01728 (14)	0.02170 (15)	0.01217 (14)	0.00052 (11)	0.00352 (11)	0.00349 (11)
S2	0.01900 (15)	0.02037 (15)	0.01232 (14)	0.00178 (11)	0.00402 (11)	0.00404 (11)
O1	0.0153 (4)	0.0165 (4)	0.0133 (4)	0.0003 (3)	0.0035 (3)	0.0025 (3)
O2	0.0161 (4)	0.0186 (4)	0.0134 (4)	−0.0014 (3)	0.0034 (3)	0.0037 (3)
N1	0.0150 (4)	0.0206 (5)	0.0132 (5)	0.0010 (4)	0.0050 (4)	0.0042 (4)
N2	0.0173 (5)	0.0166 (5)	0.0138 (5)	0.0023 (4)	0.0046 (4)	0.0051 (4)
C1	0.0328 (7)	0.0362 (7)	0.0263 (7)	0.0113 (6)	0.0175 (6)	0.0128 (6)
C2	0.0217 (6)	0.0192 (5)	0.0188 (6)	0.0016 (4)	0.0056 (5)	0.0065 (5)
C3	0.0173 (5)	0.0159 (5)	0.0151 (5)	−0.0012 (4)	0.0037 (4)	0.0012 (4)
C4	0.0134 (5)	0.0178 (5)	0.0157 (5)	0.0056 (4)	0.0060 (4)	0.0034 (4)
C5	0.0167 (5)	0.0143 (5)	0.0133 (5)	0.0044 (4)	0.0037 (4)	0.0023 (4)
C6	0.0165 (5)	0.0176 (5)	0.0178 (6)	0.0040 (4)	0.0056 (4)	0.0032 (4)
C7	0.0152 (5)	0.0198 (6)	0.0206 (6)	0.0041 (4)	0.0019 (4)	0.0019 (4)
C8	0.0237 (6)	0.0195 (5)	0.0143 (5)	0.0072 (5)	0.0015 (4)	0.0010 (4)
C9	0.0242 (6)	0.0256 (6)	0.0158 (6)	0.0067 (5)	0.0082 (5)	0.0026 (5)
C10	0.0161 (5)	0.0236 (6)	0.0168 (6)	0.0028 (4)	0.0055 (4)	0.0015 (4)
C11	0.0232 (6)	0.0278 (6)	0.0193 (6)	0.0025 (5)	0.0103 (5)	0.0042 (5)
C12	0.0211 (6)	0.0178 (5)	0.0186 (6)	0.0021 (4)	0.0068 (5)	0.0051 (4)
C13	0.0169 (5)	0.0177 (5)	0.0146 (5)	−0.0017 (4)	0.0028 (4)	0.0017 (4)
C14	0.0155 (5)	0.0164 (5)	0.0154 (5)	0.0059 (4)	0.0068 (4)	0.0037 (4)
C15	0.0128 (5)	0.0183 (5)	0.0138 (5)	0.0039 (4)	0.0046 (4)	0.0032 (4)
C16	0.0195 (5)	0.0163 (5)	0.0194 (6)	0.0054 (4)	0.0061 (5)	0.0046 (4)
C17	0.0219 (6)	0.0162 (5)	0.0197 (6)	0.0040 (4)	0.0054 (5)	−0.0003 (4)
C18	0.0193 (6)	0.0243 (6)	0.0152 (5)	0.0057 (5)	0.0035 (4)	0.0024 (5)
C19	0.0201 (5)	0.0207 (6)	0.0188 (6)	0.0071 (4)	0.0036 (5)	0.0063 (5)
C20	0.0179 (5)	0.0152 (5)	0.0188 (6)	0.0046 (4)	0.0037 (4)	0.0025 (4)

Geometric parameters (Å, º) top

S1—C4	1.6745 (12)	C7—H7	0.9500
S2—C14	1.6758 (12)	C8—C9	1.3869 (17)
O1—C4	1.3298 (14)	C8—H8	0.9500
O1—C3	1.4596 (13)	C9—C10	1.3920 (16)
O2—C14	1.3280 (14)	C9—H9	0.9500
O2—C13	1.4543 (13)	C10—H10	0.9500
N1—C4	1.3412 (15)	C11—C12	1.5213 (17)
N1—C5	1.4233 (14)	C11—H11A	0.9800
N1—H1n	0.881 (9)	C11—H11B	0.9800
N2—C14	1.3370 (15)	C11—H11C	0.9800
N2—C15	1.4277 (15)	C12—C13	1.5090 (16)
N2—H2n	0.876 (9)	C12—H12A	0.9900
C1—C2	1.5230 (18)	C12—H12B	0.9900
C1—H1A	0.9800	C13—H13A	0.9900
C1—H1B	0.9800	C13—H13B	0.9900
C1—H1C	0.9800	C15—C20	1.3908 (16)
C2—C3	1.5096 (16)	C15—C16	1.3909 (16)
C2—H2A	0.9900	C16—C17	1.3893 (17)
C2—H2B	0.9900	C16—H16	0.9500
C3—H3A	0.9900	C17—C18	1.3884 (17)
C3—H3B	0.9900	C17—H17	0.9500
C5—C10	1.3931 (16)	C18—C19	1.3910 (17)
C5—C6	1.3928 (16)	C18—H18	0.9500
C6—C7	1.3868 (16)	C19—C20	1.3901 (16)
C6—H6	0.9500	C19—H19	0.9500
C7—C8	1.3891 (18)	C20—H20	0.9500

C4—O1—C3	118.40 (9)	C10—C9—H9	119.6
C14—O2—C13	119.24 (9)	C9—C10—C5	119.44 (11)
C4—N1—C5	129.52 (10)	C9—C10—H10	120.3
C4—N1—H1n	116.3 (11)	C5—C10—H10	120.3
C5—N1—H1n	113.9 (12)	C12—C11—H11A	109.5
C14—N2—C15	128.33 (10)	C12—C11—H11B	109.5
C14—N2—H2n	116.9 (11)	H11A—C11—H11B	109.5
C15—N2—H2n	114.8 (11)	C12—C11—H11C	109.5
C2—C1—H1A	109.5	H11A—C11—H11C	109.5
C2—C1—H1B	109.5	H11B—C11—H11C	109.5
H1A—C1—H1B	109.5	C13—C12—C11	113.18 (10)
C2—C1—H1C	109.5	C13—C12—H12A	108.9
H1A—C1—H1C	109.5	C11—C12—H12A	108.9
H1B—C1—H1C	109.5	C13—C12—H12B	108.9
C3—C2—C1	112.87 (11)	C11—C12—H12B	108.9
C3—C2—H2A	109.0	H12A—C12—H12B	107.8
C1—C2—H2A	109.0	O2—C13—C12	106.33 (9)
C3—C2—H2B	109.0	O2—C13—H13A	110.5
C1—C2—H2B	109.0	C12—C13—H13A	110.5
H2A—C2—H2B	107.8	O2—C13—H13B	110.5
O1—C3—C2	107.03 (9)	C12—C13—H13B	110.5
O1—C3—H3A	110.3	H13A—C13—H13B	108.7
C2—C3—H3A	110.3	O2—C14—N2	112.77 (10)
O1—C3—H3B	110.3	O2—C14—S2	124.50 (9)
C2—C3—H3B	110.3	N2—C14—S2	122.71 (9)
H3A—C3—H3B	108.6	C20—C15—C16	120.28 (11)
O1—C4—N1	112.98 (10)	C20—C15—N2	123.06 (10)
O1—C4—S1	124.75 (8)	C16—C15—N2	116.58 (10)
N1—C4—S1	122.27 (9)	C17—C16—C15	120.03 (11)
C10—C5—C6	119.92 (11)	C17—C16—H16	120.0
C10—C5—N1	123.81 (10)	C15—C16—H16	120.0
C6—C5—N1	116.20 (10)	C16—C17—C18	120.08 (11)
C7—C6—C5	120.09 (11)	C16—C17—H17	120.0
C7—C6—H6	120.0	C18—C17—H17	120.0
C5—C6—H6	120.0	C17—C18—C19	119.60 (11)
C6—C7—C8	120.30 (11)	C17—C18—H18	120.2
C6—C7—H7	119.9	C19—C18—H18	120.2
C8—C7—H7	119.9	C20—C19—C18	120.74 (11)
C9—C8—C7	119.50 (11)	C20—C19—H19	119.6
C9—C8—H8	120.2	C18—C19—H19	119.6
C7—C8—H8	120.2	C19—C20—C15	119.27 (11)
C8—C9—C10	120.75 (11)	C19—C20—H20	120.4
C8—C9—H9	119.6	C15—C20—H20	120.4

C4—O1—C3—C2	179.25 (10)	C14—O2—C13—C12	179.29 (10)
C1—C2—C3—O1	−66.95 (13)	C11—C12—C13—O2	55.92 (13)
C3—O1—C4—N1	179.65 (9)	C13—O2—C14—N2	174.58 (9)
C3—O1—C4—S1	−0.49 (14)	C13—O2—C14—S2	−4.13 (15)
C5—N1—C4—O1	0.59 (17)	C15—N2—C14—O2	0.88 (17)
C5—N1—C4—S1	−179.27 (9)	C15—N2—C14—S2	179.63 (9)
C4—N1—C5—C10	37.09 (18)	C14—N2—C15—C20	39.15 (18)
C4—N1—C5—C6	−146.20 (12)	C14—N2—C15—C16	−144.15 (12)
C10—C5—C6—C7	0.15 (17)	C20—C15—C16—C17	−0.04 (17)
N1—C5—C6—C7	−176.70 (10)	N2—C15—C16—C17	−176.84 (10)
C5—C6—C7—C8	−0.78 (18)	C15—C16—C17—C18	−0.51 (18)
C6—C7—C8—C9	0.79 (18)	C16—C17—C18—C19	0.26 (18)
C7—C8—C9—C10	−0.17 (19)	C17—C18—C19—C20	0.53 (18)
C8—C9—C10—C5	−0.46 (19)	C18—C19—C20—C15	−1.07 (18)
C6—C5—C10—C9	0.47 (18)	C16—C15—C20—C19	0.82 (17)
N1—C5—C10—C9	177.06 (11)	N2—C15—C20—C19	177.41 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···S2	0.88 (1)	2.51 (1)	3.3667 (10)	164 (2)
N2—H2n···S1	0.88 (1)	2.52 (1)	3.3765 (10)	167 (2)

Experimental details

Crystal data
Chemical formula	C₁₀H₁₃NOS
M_r	195.27
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.9230 (4), 9.8752 (4), 12.9613 (5)
α, β, γ (°)	98.037 (3), 105.866 (4), 104.533 (4)
V (Å³)	1036.46 (7)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	2.45
Crystal size (mm)	0.35 × 0.30 × 0.25

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.772, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7531, 4249, 4049
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.631

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.081, 1.04
No. of reflections	4249
No. of parameters	243
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.26

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006) and QMol (Gans & Shalloway, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···S2	0.881 (9)	2.511 (10)	3.3667 (10)	163.8 (15)
N2—H2n···S1	0.876 (9)	2.518 (10)	3.3765 (10)	166.9 (15)

Acknowledgements

PS thanks the Development and Promotion of Science and Technology Talents Project (DPST), Thailand, for support to enable study at the University of Malaya. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

References

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