O-Propyl N-phenyl-thio-carbamate.

Two independent mol-ecules comprise the asymmetric unit in the title thio-carbamide derivative, C(10)H(13)NOS. 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 = phen-yl]. The independent mol-ecules are linked into a dimeric aggregate by N-H⋯S hydrogen bonds and an eight-membered thio-amide {⋯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 = 195.27

Triclinic,

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[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.081

S = 1.04

4249 reflections

243 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.26 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681202140X/hg5228sup1.cif

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

Supplementary material file. DOI: 10.1107/S160053681202140X/hg5228Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H13NOS	Z = 4
Mr = 195.27	F(000) = 416
Triclinic, P1	Dx = 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

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	Rint = 0.014
Detector resolution: 10.4041 pixels mm-1	θmax = 76.6°, θmin = 4.8°
ω scan	h = −7→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −11→12
Tmin = 0.772, Tmax = 1.000	l = −15→16
7531 measured reflections

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(Fo2) + (0.0468P)2 + 0.325P] where P = (Fo2 + 2Fc2)/3
4249 reflections	(Δ/σ)max = 0.001
243 parameters	Δρmax = 0.22 e Å−3
2 restraints	Δρmin = −0.26 e Å−3

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
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)*

	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)

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)

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)

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)