N-Benzoyl-N',N'-dimethyl-thio-urea.

In the title compound, C(10)H(12)N(2)OS, the amide NCO group is twisted relative to the thio-ureido SCN(2) group, forming a dihedral angle of 55.3 (2)°. The crystal packing shows inter-molecular N-H⋯S and weak C-H⋯O inter-actions, the former giving rise to the formation of centrosymmetric R(2) (2)(8) dimers.

Related literature

For general background to N-acyl-N′,N′-disubstituted thio­urea, see: Koch (2001 ▶); Sosa-Albertus & Piris (2001 ▶); Pérez et al. (2008a ▶). For related structures, see: Arslan et al. (2003 ▶); Bolte & Fink (2003 ▶); Pérez et al. (2008b ▶); Gomes et al. (2010 ▶). For details of the synthesis, see: Nagasawa & Mitsunobu (1981 ▶); Che et al. (1999 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C10H12N2OS

M = 208.28

Monoclinic,

a = 10.8602 (9) Å

b = 5.5590 (6) Å

c = 18.6864 (10) Å

β = 102.768 (5)°

V = 1100.24 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 294 K

0.26 × 0.13 × 0.13 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: gaussian (Coppens et al., 1965 ▶) T min = 0.943, T max = 0.969

7078 measured reflections

2282 independent reflections

1762 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.120

S = 1.05

2282 reflections

133 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.27 e Å−3

Data collection: COLLECT (Enraf–Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor 1997 ▶); data reduction: DENZO (Otwinowski & Minor 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811005137/gk2336sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811005137/gk2336Isup2.hkl

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

C10H12N2OS	F(000) = 440
Mr = 208.28	Dx = 1.257 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1912 reflections
a = 10.8602 (9) Å	θ = 3.5–26.7°
b = 5.5590 (6) Å	µ = 0.26 mm−1
c = 18.6864 (10) Å	T = 294 K
β = 102.768 (5)°	Prism, colourless
V = 1100.24 (16) Å3	0.26 × 0.13 × 0.13 mm
Z = 4

Nonius KappaCCD diffractometer	1762 reflections with I > 2σ(I)
ω scan	Rint = 0.041
Absorption correction: gaussian (Coppens et al., 1965)	θmax = 26.7°, θmin = 3.5°
Tmin = 0.943, Tmax = 0.969	h = −13→13
7078 measured reflections	k = −6→7
2282 independent reflections	l = −22→23

Refinement on F2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.043	w = 1/[σ2(Fo2) + (0.0587P)2 + 0.1899P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.120	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.17 e Å−3
2282 reflections	Δρmin = −0.27 e Å−3
133 parameters

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.

	x	y	z	Uiso*/Ueq
C1	0.55382 (16)	0.7917 (3)	0.35288 (9)	0.0475 (4)
C2	0.38501 (16)	0.6859 (3)	0.41573 (8)	0.0459 (4)
C3	0.69073 (16)	0.8469 (3)	0.36576 (9)	0.0484 (4)
C4	0.7314 (2)	1.0217 (4)	0.32357 (10)	0.0638 (5)
H4	0.6731	1.103	0.2878	0.077*
C5	0.8583 (2)	1.0756 (5)	0.33449 (13)	0.0778 (6)
H5	0.8853	1.1951	0.3067	0.093*
C6	0.9442 (2)	0.9537 (5)	0.38608 (14)	0.0822 (7)
H6	1.0296	0.9899	0.393	0.099*
C7	0.90569 (19)	0.7787 (5)	0.42771 (14)	0.0785 (6)
H7	0.965	0.6965	0.4627	0.094*
C8	0.77898 (18)	0.7235 (4)	0.41797 (11)	0.0608 (5)
H8	0.7529	0.6042	0.4463	0.073*
C9	0.3971 (3)	0.3391 (4)	0.33595 (14)	0.0806 (7)
H9A	0.4844	0.3341	0.3609	0.121*
H9B	0.3906	0.3891	0.2861	0.121*
H9C	0.3607	0.182	0.3366	0.121*
C10	0.19432 (19)	0.4648 (5)	0.36413 (12)	0.0753 (6)
H10A	0.1503	0.6153	0.3619	0.113*
H10B	0.1803	0.373	0.4051	0.113*
H10C	0.1636	0.3765	0.3196	0.113*
N1	0.51125 (13)	0.7326 (3)	0.41555 (8)	0.0485 (4)
N2	0.32963 (14)	0.5100 (3)	0.37299 (8)	0.0557 (4)
O1	0.48381 (12)	0.7991 (3)	0.29255 (6)	0.0623 (4)
S1	0.31430 (4)	0.84543 (10)	0.47135 (3)	0.0602 (2)
H1	0.5514 (19)	0.802 (4)	0.4545 (11)	0.066 (6)*

	U11	U22	U33	U12	U13	U23
C1	0.0508 (9)	0.0491 (10)	0.0440 (8)	0.0049 (7)	0.0133 (7)	−0.0020 (7)
C2	0.0449 (9)	0.0501 (10)	0.0416 (8)	−0.0028 (7)	0.0073 (6)	0.0012 (7)
C3	0.0505 (9)	0.0528 (10)	0.0452 (8)	0.0041 (7)	0.0176 (7)	−0.0013 (7)
C4	0.0672 (12)	0.0686 (13)	0.0596 (11)	0.0016 (10)	0.0228 (9)	0.0091 (9)
C5	0.0744 (14)	0.0826 (15)	0.0854 (14)	−0.0127 (12)	0.0369 (12)	0.0106 (13)
C6	0.0530 (12)	0.0933 (18)	0.1055 (17)	−0.0082 (11)	0.0288 (12)	0.0052 (15)
C7	0.0476 (11)	0.0905 (16)	0.0961 (16)	0.0084 (11)	0.0130 (11)	0.0168 (13)
C8	0.0541 (11)	0.0630 (12)	0.0669 (11)	0.0047 (9)	0.0170 (9)	0.0115 (9)
C9	0.0980 (17)	0.0543 (12)	0.0940 (16)	−0.0025 (11)	0.0312 (14)	−0.0231 (11)
C10	0.0614 (12)	0.0833 (16)	0.0749 (13)	−0.0227 (11)	0.0017 (10)	−0.0145 (11)
N1	0.0435 (8)	0.0610 (9)	0.0410 (7)	−0.0033 (6)	0.0093 (6)	−0.0038 (7)
N2	0.0561 (9)	0.0519 (9)	0.0582 (8)	−0.0062 (7)	0.0106 (7)	−0.0106 (7)
O1	0.0590 (8)	0.0824 (10)	0.0436 (7)	0.0056 (6)	0.0075 (6)	0.0021 (6)
S1	0.0504 (3)	0.0722 (4)	0.0626 (3)	−0.0118 (2)	0.0222 (2)	−0.0184 (2)

C1—O1	1.2133 (19)	C6—H6	0.93
C1—N1	1.390 (2)	C7—C8	1.382 (3)
C1—C3	1.485 (2)	C7—H7	0.93
C2—N2	1.321 (2)	C8—H8	0.93
C2—N1	1.396 (2)	C9—N2	1.464 (3)
C2—S1	1.6759 (17)	C9—H9A	0.96
C3—C4	1.384 (3)	C9—H9B	0.96
C3—C8	1.388 (3)	C9—H9C	0.96
C4—C5	1.381 (3)	C10—N2	1.464 (2)
C4—H4	0.93	C10—H10A	0.96
C5—C6	1.364 (3)	C10—H10B	0.96
C5—H5	0.93	C10—H10C	0.96
C6—C7	1.368 (3)	N1—H1	0.85 (2)
O1—C1—N1	122.28 (16)	C7—C8—C3	119.70 (19)
O1—C1—C3	122.89 (15)	C7—C8—H8	120.1
N1—C1—C3	114.83 (14)	C3—C8—H8	120.1
N2—C2—N1	116.90 (15)	N2—C9—H9A	109.5
N2—C2—S1	123.85 (14)	N2—C9—H9B	109.5
N1—C2—S1	119.21 (12)	H9A—C9—H9B	109.5
C4—C3—C8	119.31 (17)	N2—C9—H9C	109.5
C4—C3—C1	119.15 (16)	H9A—C9—H9C	109.5
C8—C3—C1	121.52 (16)	H9B—C9—H9C	109.5
C5—C4—C3	120.14 (19)	N2—C10—H10A	109.5
C5—C4—H4	119.9	N2—C10—H10B	109.5
C3—C4—H4	119.9	H10A—C10—H10B	109.5
C6—C5—C4	120.0 (2)	N2—C10—H10C	109.5
C6—C5—H5	120	H10A—C10—H10C	109.5
C4—C5—H5	120	H10B—C10—H10C	109.5
C5—C6—C7	120.5 (2)	C1—N1—C2	123.76 (14)
C5—C6—H6	119.7	C1—N1—H1	114.1 (14)
C7—C6—H6	119.7	C2—N1—H1	113.5 (14)
C6—C7—C8	120.3 (2)	C2—N2—C10	120.48 (16)
C6—C7—H7	119.9	C2—N2—C9	123.91 (17)
C8—C7—H7	119.9	C10—N2—C9	115.48 (17)
O1—C1—C3—C4	34.5 (3)	C4—C3—C8—C7	0.8 (3)
N1—C1—C3—C4	−144.94 (17)	C1—C3—C8—C7	179.32 (19)
O1—C1—C3—C8	−144.04 (19)	O1—C1—N1—C2	−2.6 (3)
N1—C1—C3—C8	36.5 (2)	C3—C1—N1—C2	176.89 (15)
C8—C3—C4—C5	−1.3 (3)	N2—C2—N1—C1	57.9 (2)
C1—C3—C4—C5	−179.87 (19)	S1—C2—N1—C1	−124.37 (16)
C3—C4—C5—C6	1.1 (3)	N1—C2—N2—C10	−173.79 (17)
C4—C5—C6—C7	−0.4 (4)	S1—C2—N2—C10	8.6 (2)
C5—C6—C7—C8	−0.1 (4)	N1—C2—N2—C9	10.6 (3)
C6—C7—C8—C3	−0.1 (4)	S1—C2—N2—C9	−167.03 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1i	0.85 (2)	2.65 (2)	3.4335 (17)	154.2 (18)
C9—H9A···N1	0.96	2.43	2.778 (3)	101
C9—H9B···O1	0.96	2.49	2.902 (3)	106
C10—H10C···O1ii	0.96	2.38	3.265 (3)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S1i	0.85 (2)	2.65 (2)	3.4335 (17)	154.2 (18)
C10—H10C⋯O1ii	0.96	2.38	3.265 (3)	153

Symmetry codes: (i) ; (ii) .