3-Acetyl-1-(2-methylphenyl)thiourea.

In the title compound, C(10)H(12)N(2)OS, the toluene and the N-carbamothio-ylacetamide units are oriented at dihedral angle of 78.75 (5)°. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring. In the crystal, mol-ecules are linked into [101] chains by pairs of N-H⋯S hydrogen bonds [which generate R(2) (2)(8) loops] and pairs of O-H⋯O hydrogen bonds [which generate R(2) (2)(4) loops]. The two motifs alternate in the chain.

Related literature

For related structures, see: Shahwar et al. (2012 ▶). For graph–set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C10H12N2OS

M = 208.28

Monoclinic,

a = 5.0444 (2) Å

b = 20.7019 (9) Å

c = 9.9464 (4) Å

β = 95.116 (2)°

V = 1034.55 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 296 K

0.35 × 0.15 × 0.13 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.915, T max = 0.938

7696 measured reflections

1812 independent reflections

1512 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.088

S = 1.17

1812 reflections

129 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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 PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812011658/hb6692sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812011658/hb6692Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812011658/hb6692Isup3.cml

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

C10H12N2OS	F(000) = 440
Mr = 208.28	Dx = 1.337 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1513 reflections
a = 5.0444 (2) Å	θ = 2.0–25.2°
b = 20.7019 (9) Å	µ = 0.28 mm−1
c = 9.9464 (4) Å	T = 296 K
β = 95.116 (2)°	Needle, white
V = 1034.55 (7) Å3	0.35 × 0.15 × 0.13 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	1812 independent reflections
Radiation source: fine-focus sealed tube	1512 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 8.00 pixels mm-1	θmax = 25.2°, θmin = 2.0°
ω scans	h = −5→6
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −24→22
Tmin = 0.915, Tmax = 0.938	l = −11→11
7696 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H-atom parameters constrained
S = 1.17	w = 1/[σ2(Fo2) + (0.0311P)2 + 0.355P] where P = (Fo2 + 2Fc2)/3
1812 reflections	(Δ/σ)max < 0.001
129 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.39407 (11)	0.07983 (3)	0.11730 (5)	0.0401 (2)
O1	1.0674 (3)	−0.02473 (7)	0.36353 (14)	0.0456 (5)
N1	0.7141 (3)	0.07120 (8)	0.34350 (16)	0.0337 (5)
N2	0.7701 (3)	−0.00655 (8)	0.18163 (16)	0.0326 (5)
C1	0.5997 (4)	0.12750 (10)	0.40024 (19)	0.0312 (6)
C2	0.6773 (4)	0.18879 (10)	0.3631 (2)	0.0348 (7)
C3	0.5651 (4)	0.24080 (11)	0.4260 (2)	0.0440 (8)
C4	0.3876 (4)	0.23224 (12)	0.5219 (2)	0.0493 (8)
C5	0.3150 (5)	0.17099 (12)	0.5564 (2)	0.0491 (8)
C6	0.4207 (4)	0.11826 (11)	0.4958 (2)	0.0399 (7)
C7	0.8746 (4)	0.19878 (12)	0.2608 (2)	0.0462 (8)
C8	0.6379 (4)	0.04791 (9)	0.22219 (19)	0.0294 (6)
C9	0.9799 (4)	−0.03869 (10)	0.2492 (2)	0.0334 (7)
C10	1.0907 (4)	−0.09266 (11)	0.1711 (2)	0.0456 (8)
H1	0.83956	0.05146	0.39124	0.0404*
H2	0.71344	−0.02218	0.10425	0.0391*
H3	0.61134	0.28255	0.40262	0.0528*
H4	0.31710	0.26787	0.56314	0.0591*
H5	0.19428	0.16508	0.62076	0.0589*
H6	0.37200	0.07669	0.51911	0.0478*
H7A	0.79640	0.18600	0.17331	0.0692*
H7B	1.03029	0.17317	0.28474	0.0692*
H7C	0.92326	0.24358	0.25886	0.0692*
H10A	1.21650	−0.11680	0.22928	0.0684*
H10B	1.17794	−0.07517	0.09732	0.0684*
H10C	0.94861	−0.12060	0.13674	0.0684*

	U11	U22	U33	U12	U13	U23
S1	0.0437 (3)	0.0418 (3)	0.0328 (3)	0.0132 (3)	−0.0077 (2)	−0.0084 (3)
O1	0.0543 (9)	0.0469 (10)	0.0337 (9)	0.0164 (7)	−0.0069 (7)	−0.0033 (7)
N1	0.0381 (9)	0.0333 (10)	0.0284 (9)	0.0089 (7)	−0.0038 (7)	−0.0049 (7)
N2	0.0363 (9)	0.0318 (10)	0.0289 (9)	0.0056 (7)	−0.0007 (7)	−0.0084 (7)
C1	0.0328 (10)	0.0321 (11)	0.0272 (10)	0.0042 (9)	−0.0048 (8)	−0.0054 (9)
C2	0.0321 (11)	0.0369 (12)	0.0346 (11)	−0.0007 (9)	−0.0013 (9)	−0.0017 (10)
C3	0.0483 (13)	0.0303 (12)	0.0527 (14)	−0.0017 (10)	0.0010 (11)	−0.0058 (11)
C4	0.0546 (14)	0.0419 (14)	0.0519 (15)	0.0060 (11)	0.0082 (12)	−0.0167 (12)
C5	0.0532 (14)	0.0556 (16)	0.0409 (13)	0.0045 (12)	0.0173 (11)	−0.0064 (12)
C6	0.0462 (12)	0.0376 (13)	0.0361 (12)	−0.0007 (10)	0.0057 (10)	0.0002 (10)
C7	0.0451 (13)	0.0466 (14)	0.0474 (14)	−0.0053 (11)	0.0077 (10)	0.0029 (11)
C8	0.0316 (10)	0.0289 (11)	0.0278 (10)	−0.0013 (9)	0.0041 (8)	−0.0022 (8)
C9	0.0357 (11)	0.0322 (11)	0.0326 (12)	0.0035 (9)	0.0043 (9)	0.0022 (9)
C10	0.0503 (13)	0.0436 (14)	0.0429 (13)	0.0158 (11)	0.0041 (10)	−0.0044 (11)

S1—C8	1.676 (2)	C4—C5	1.372 (3)
O1—C9	1.217 (2)	C5—C6	1.377 (3)
N1—C1	1.438 (3)	C9—C10	1.497 (3)
N1—C8	1.324 (2)	C3—H3	0.9300
N2—C8	1.388 (3)	C4—H4	0.9300
N2—C9	1.374 (3)	C5—H5	0.9300
N1—H1	0.8600	C6—H6	0.9300
N2—H2	0.8600	C7—H7A	0.9600
C1—C2	1.388 (3)	C7—H7B	0.9600
C1—C6	1.381 (3)	C7—H7C	0.9600
C2—C7	1.500 (3)	C10—H10A	0.9600
C2—C3	1.391 (3)	C10—H10B	0.9600
C3—C4	1.377 (3)	C10—H10C	0.9600
C1—N1—C8	123.96 (16)	O1—C9—N2	122.77 (19)
C8—N2—C9	128.34 (17)	C2—C3—H3	119.00
C1—N1—H1	118.00	C4—C3—H3	119.00
C8—N1—H1	118.00	C3—C4—H4	120.00
C8—N2—H2	116.00	C5—C4—H4	120.00
C9—N2—H2	116.00	C4—C5—H5	120.00
N1—C1—C2	120.27 (17)	C6—C5—H5	120.00
N1—C1—C6	117.88 (18)	C1—C6—H6	120.00
C2—C1—C6	121.80 (19)	C5—C6—H6	120.00
C3—C2—C7	121.32 (19)	C2—C7—H7A	109.00
C1—C2—C3	116.90 (18)	C2—C7—H7B	109.00
C1—C2—C7	121.79 (19)	C2—C7—H7C	109.00
C2—C3—C4	121.9 (2)	H7A—C7—H7B	109.00
C3—C4—C5	119.8 (2)	H7A—C7—H7C	109.00
C4—C5—C6	120.1 (2)	H7B—C7—H7C	109.00
C1—C6—C5	119.6 (2)	C9—C10—H10A	109.00
S1—C8—N1	124.12 (15)	C9—C10—H10B	109.00
S1—C8—N2	118.97 (14)	C9—C10—H10C	109.00
N1—C8—N2	116.91 (17)	H10A—C10—H10B	109.00
O1—C9—C10	122.74 (18)	H10A—C10—H10C	109.00
N2—C9—C10	114.49 (17)	H10B—C10—H10C	110.00
C8—N1—C1—C2	−79.9 (3)	C6—C1—C2—C3	−0.4 (3)
C8—N1—C1—C6	102.7 (2)	C6—C1—C2—C7	179.11 (19)
C1—N1—C8—S1	−0.9 (3)	N1—C1—C6—C5	177.42 (18)
C1—N1—C8—N2	179.42 (17)	C2—C1—C6—C5	0.1 (3)
C9—N2—C8—S1	177.45 (16)	C1—C2—C3—C4	0.8 (3)
C9—N2—C8—N1	−2.8 (3)	C7—C2—C3—C4	−178.76 (19)
C8—N2—C9—O1	5.5 (3)	C2—C3—C4—C5	−0.8 (3)
C8—N2—C9—C10	−175.01 (18)	C3—C4—C5—C6	0.4 (3)
N1—C1—C2—C3	−177.70 (17)	C4—C5—C6—C1	−0.1 (3)
N1—C1—C2—C7	1.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	1.99	2.664 (2)	135
N1—H1···O1i	0.86	2.50	3.172 (2)	135
N2—H2···S1ii	0.86	2.52	3.3747 (17)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.86	1.99	2.664 (2)	135
N1—H1⋯O1i	0.86	2.50	3.172 (2)	135
N2—H2⋯S1ii	0.86	2.52	3.3747 (17)	171

Symmetry codes: (i) ; (ii) .