3-Acetyl-1-(3-methyl-phen-yl)thio-urea.

In the crystal structure of the title compound, C(10)H(12)N(2)OS, the conformation of the two N-H bonds are anti to each other. The amide C=O and the C=S are are also anti to each other. The N-H bond adjacent to the benzene ring is syn to the m-methyl groups. The dihedral angle between the benzene ring and the side chain [mean plane of atoms C-C(O)N-C-N; maximum deviation 0.029 (2) Å] is 14.30 (7)°. There is an intramolecular N-H⋯O hydrogen bond generating an S(6) ring motif. In the crystal, the molecules are linked via N-H⋯) hydrogen bonds, forming chains propagating along [001]. The S atom is disordered and was refined using a split model [occupancy ratio 0.56 (4):0.44 (4)].

Related literature

For studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Alkan et al. (2011 ▶); Bhat & Gowda (2000 ▶); Bowes et al. (2003 ▶); Gowda et al. (2000 ▶); Saeed et al. (2010 ▶); Shahwar et al. (2012 ▶), of N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007 ▶) and of N-chloro­aryl­sulfonamides, see: Gowda & Ramachandra (1989 ▶); Jyothi & Gowda (2004 ▶); Shetty & Gowda (2004 ▶).

Experimental

Crystal data

C10H12N2OS

M = 208.29

Monoclinic,

a = 7.6841 (9) Å

b = 14.943 (1) Å

c = 9.5358 (9) Å

β = 107.49 (1)°

V = 1044.32 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 295 K

0.48 × 0.44 × 0.24 mm

Data collection

Oxford Diffraction Xcalibur Sapphire CCD. diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.878, T max = 0.936

4011 measured reflections

2137 independent reflections

1789 reflections with I > 2σ(I)

R int = 0.011

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.100

S = 1.06

2137 reflections

145 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812032825/rk2375sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032825/rk2375Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812032825/rk2375Isup3.cml

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

C10H12N2OS	F(000) = 440
Mr = 208.29	Dx = 1.325 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1948 reflections
a = 7.6841 (9) Å	θ = 2.6–27.9°
b = 14.943 (1) Å	µ = 0.28 mm−1
c = 9.5358 (9) Å	T = 295 K
β = 107.49 (1)°	Prism, yellow
V = 1044.32 (18) Å3	0.48 × 0.44 × 0.24 mm
Z = 4

Oxford Diffraction Xcalibur Sapphire CCD. diffractometer	2137 independent reflections
Radiation source: fine-focus sealed tube	1789 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.011
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −9→8
Tmin = 0.878, Tmax = 0.936	k = −13→18
4011 measured reflections	l = −9→11

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0535P)2 + 0.2352P] where P = (Fo2 + 2Fc2)/3
2137 reflections	(Δ/σ)max = 0.001
145 parameters	Δρmax = 0.17 e Å−3
2 restraints	Δρmin = −0.22 e Å−3

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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)
C1	0.20722 (18)	1.01499 (9)	0.39974 (15)	0.0337 (3)
C2	0.23877 (19)	1.03395 (10)	0.54780 (17)	0.0364 (3)
H2	0.3113	0.9953	0.6178	0.044*
C3	0.1649 (2)	1.10903 (10)	0.59419 (18)	0.0413 (4)
C4	0.0590 (2)	1.16622 (11)	0.4881 (2)	0.0494 (4)
H4	0.0085	1.2171	0.5163	0.059*
C5	0.0282 (2)	1.14793 (11)	0.3408 (2)	0.0506 (4)
H5	−0.0429	1.1871	0.2710	0.061*
C6	0.1008 (2)	1.07243 (10)	0.29439 (18)	0.0428 (4)
H6	0.0785	1.0607	0.1948	0.051*
C7	0.30263 (18)	0.89953 (9)	0.24567 (15)	0.0334 (3)
C8	0.4388 (2)	0.76042 (10)	0.38195 (15)	0.0361 (3)
C9	0.5236 (3)	0.67388 (11)	0.35913 (18)	0.0520 (4)
H9A	0.6484	0.6724	0.4198	0.078*
H9B	0.5190	0.6685	0.2577	0.078*
H9C	0.4580	0.6251	0.3851	0.078*
C10	0.1971 (2)	1.12586 (13)	0.7555 (2)	0.0539 (4)
H10A	0.2948	1.0885	0.8117	0.081*
H10B	0.0880	1.1123	0.7807	0.081*
H10C	0.2289	1.1875	0.7772	0.081*
N1	0.28202 (17)	0.93305 (8)	0.36952 (13)	0.0354 (3)
H1N	0.323 (2)	0.8973 (10)	0.4440 (16)	0.042*
N2	0.37949 (17)	0.81347 (8)	0.26055 (13)	0.0344 (3)
H2N	0.391 (2)	0.7951 (11)	0.1792 (16)	0.041*
O1	0.42351 (17)	0.78202 (7)	0.50180 (11)	0.0483 (3)
S1A	0.2654 (12)	0.9501 (3)	0.0852 (7)	0.0498 (10)	0.56 (4)
S1B	0.234 (2)	0.9416 (8)	0.0776 (9)	0.0656 (16)	0.44 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0337 (7)	0.0314 (7)	0.0377 (8)	−0.0023 (6)	0.0131 (6)	−0.0005 (6)
C2	0.0353 (7)	0.0366 (8)	0.0373 (7)	−0.0019 (6)	0.0106 (6)	−0.0014 (6)
C3	0.0392 (8)	0.0389 (8)	0.0495 (9)	−0.0076 (6)	0.0191 (7)	−0.0089 (7)
C4	0.0506 (9)	0.0353 (8)	0.0676 (11)	0.0024 (7)	0.0256 (8)	−0.0049 (8)
C5	0.0517 (9)	0.0398 (9)	0.0612 (11)	0.0092 (7)	0.0182 (8)	0.0120 (8)
C6	0.0461 (8)	0.0421 (8)	0.0402 (8)	0.0039 (7)	0.0129 (7)	0.0052 (7)
C7	0.0344 (7)	0.0363 (7)	0.0299 (7)	−0.0020 (6)	0.0103 (5)	0.0014 (6)
C8	0.0471 (8)	0.0337 (7)	0.0297 (7)	−0.0007 (6)	0.0150 (6)	0.0016 (6)
C9	0.0795 (12)	0.0421 (9)	0.0397 (9)	0.0143 (8)	0.0256 (8)	0.0051 (7)
C10	0.0549 (10)	0.0569 (11)	0.0547 (10)	−0.0057 (8)	0.0238 (8)	−0.0196 (8)
N1	0.0451 (7)	0.0337 (6)	0.0273 (6)	0.0047 (5)	0.0108 (5)	0.0027 (5)
N2	0.0456 (7)	0.0344 (6)	0.0254 (6)	0.0008 (5)	0.0140 (5)	−0.0008 (5)
O1	0.0791 (8)	0.0417 (6)	0.0292 (6)	0.0119 (5)	0.0242 (5)	0.0047 (4)
S1A	0.078 (2)	0.043 (2)	0.0358 (14)	0.0165 (11)	0.0274 (16)	0.0155 (6)
S1B	0.076 (3)	0.091 (4)	0.0285 (11)	0.031 (2)	0.0134 (15)	0.0141 (17)

C1—C6	1.386 (2)	C7—S1A	1.653 (5)
C1—C2	1.388 (2)	C7—S1B	1.654 (7)
C1—N1	1.4186 (18)	C8—O1	1.2268 (17)
C2—C3	1.388 (2)	C8—N2	1.3636 (18)
C2—H2	0.9300	C8—C9	1.493 (2)
C3—C4	1.386 (2)	C9—H9A	0.9600
C3—C10	1.504 (2)	C9—H9B	0.9600
C4—C5	1.379 (3)	C9—H9C	0.9600
C4—H4	0.9300	C10—H10A	0.9600
C5—C6	1.389 (2)	C10—H10B	0.9600
C5—H5	0.9300	C10—H10C	0.9600
C6—H6	0.9300	N1—H1N	0.868 (13)
C7—N1	1.3354 (18)	N2—H2N	0.853 (14)
C7—N2	1.4044 (19)
C6—C1—C2	119.71 (14)	S1A—C7—S1B	9.2 (7)
C6—C1—N1	125.04 (13)	O1—C8—N2	122.46 (13)
C2—C1—N1	115.17 (13)	O1—C8—C9	122.14 (13)
C3—C2—C1	121.73 (14)	N2—C8—C9	115.40 (13)
C3—C2—H2	119.1	C8—C9—H9A	109.5
C1—C2—H2	119.1	C8—C9—H9B	109.5
C4—C3—C2	118.18 (15)	H9A—C9—H9B	109.5
C4—C3—C10	121.56 (15)	C8—C9—H9C	109.5
C2—C3—C10	120.25 (15)	H9A—C9—H9C	109.5
C5—C4—C3	120.29 (15)	H9B—C9—H9C	109.5
C5—C4—H4	119.9	C3—C10—H10A	109.5
C3—C4—H4	119.9	C3—C10—H10B	109.5
C4—C5—C6	121.54 (16)	H10A—C10—H10B	109.5
C4—C5—H5	119.2	C3—C10—H10C	109.5
C6—C5—H5	119.2	H10A—C10—H10C	109.5
C1—C6—C5	118.55 (15)	H10B—C10—H10C	109.5
C1—C6—H6	120.7	C7—N1—C1	131.79 (12)
C5—C6—H6	120.7	C7—N1—H1N	112.6 (11)
N1—C7—N2	114.34 (12)	C1—N1—H1N	115.7 (11)
N1—C7—S1A	127.9 (2)	C8—N2—C7	129.89 (12)
N2—C7—S1A	117.58 (19)	C8—N2—H2N	119.0 (11)
N1—C7—S1B	128.8 (3)	C7—N2—H2N	111.0 (11)
N2—C7—S1B	116.6 (3)
C6—C1—C2—C3	0.6 (2)	N2—C7—N1—C1	−178.23 (13)
N1—C1—C2—C3	−176.12 (12)	S1A—C7—N1—C1	7.4 (5)
C1—C2—C3—C4	−0.8 (2)	S1B—C7—N1—C1	−4.2 (10)
C1—C2—C3—C10	178.03 (14)	C6—C1—N1—C7	14.7 (2)
C2—C3—C4—C5	0.3 (2)	C2—C1—N1—C7	−168.76 (14)
C10—C3—C4—C5	−178.41 (16)	O1—C8—N2—C7	3.5 (2)
C3—C4—C5—C6	0.2 (3)	C9—C8—N2—C7	−176.63 (14)
C2—C1—C6—C5	−0.1 (2)	N1—C7—N2—C8	−1.4 (2)
N1—C1—C6—C5	176.32 (14)	S1A—C7—N2—C8	173.5 (4)
C4—C5—C6—C1	−0.3 (2)	S1B—C7—N2—C8	−176.3 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.87 (1)	1.90 (2)	2.6536 (16)	144 (2)
N2—H2N···O1i	0.85 (1)	2.12 (1)	2.9564 (16)	166 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1	0.87 (1)	1.90 (2)	2.6536 (16)	144 (2)
N2—H2N⋯O1i	0.85 (1)	2.12 (1)	2.9564 (16)	166 (2)

Symmetry code: (i) .