3-Acetyl-1-(2,3-dimethyl-phen-yl)thio-urea.

In the crystal structure of the title compound, C(11)H(14)N(2)OS, the conformation of the two N-H bonds is anti. The conformation of the C=S and the C=O bonds is also anti. Furthermore, the N-H bond adjacent to the benzene ring is anti to the ortho- and meta-methyl groups. The dihedral angle between the benzene ring and the side chain [N-C(= S)-N-C(=O)-C; maximum deviation = 0.047 (4) Å] is 81.33 (10)°. The NH hydrogen adjacent to the benzene ring and the amide O atom exhibit bifurcated intra- and inter-molecular hydrogen bonding. In the crystal, mol-ecules form inversion dimers, which are linked into chains via R(2) (2)(12) and R(2) (2)(8) networks.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Bhat & Gowda (2000 ▶); Gowda et al. (2006 ▶); Shahwar et al. (2012 ▶), of N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007 ▶) and of N-chloro­aryl­sulfonamides, see: Jyothi & Gowda (2004 ▶); Shetty & Gowda (2004 ▶).

Experimental

Crystal data

C11H14N2OS

M = 222.30

Triclinic,

a = 5.0552 (7) Å

b = 9.869 (2) Å

c = 12.028 (3) Å

α = 106.71 (1)°

β = 91.01 (1)°

γ = 94.57 (1)°

V = 572.4 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 293 K

0.48 × 0.08 × 0.04 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.886, T max = 0.990

3414 measured reflections

2066 independent reflections

1331 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.141

S = 1.08

2066 reflections

145 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.24 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/S1600536812027973/nc2285sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812027973/nc2285Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812027973/nc2285Isup3.cml

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

C11H14N2OS	Z = 2
Mr = 222.30	F(000) = 236
Triclinic, P1	Dx = 1.290 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.0552 (7) Å	Cell parameters from 1147 reflections
b = 9.869 (2) Å	θ = 3.5–27.8°
c = 12.028 (3) Å	µ = 0.26 mm−1
α = 106.71 (1)°	T = 293 K
β = 91.01 (1)°	Needle, colourless
γ = 94.57 (1)°	0.48 × 0.08 × 0.04 mm
V = 572.4 (2) Å3

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2066 independent reflections
Radiation source: fine-focus sealed tube	1331 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Rotation method data acquisition using ω and phi scans	θmax = 25.3°, θmin = 3.5°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −6→6
Tmin = 0.886, Tmax = 0.990	k = −11→11
3414 measured reflections	l = −13→14

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0493P)2 + 0.4018P] where P = (Fo2 + 2Fc2)/3
2066 reflections	(Δ/σ)max = 0.003
145 parameters	Δρmax = 0.33 e Å−3
5 restraints	Δρmin = −0.24 e Å−3

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

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	1.1098 (2)	0.43318 (11)	0.14467 (9)	0.0458 (3)
O1	0.4254 (5)	0.1213 (3)	−0.0465 (2)	0.0552 (8)
N1	0.7872 (6)	0.2041 (3)	0.1289 (3)	0.0432 (8)
H1N	0.674 (6)	0.140 (3)	0.086 (3)	0.052*
N2	0.7252 (6)	0.3141 (3)	−0.0129 (3)	0.0382 (7)
H2N	0.773 (7)	0.378 (3)	−0.043 (3)	0.046*
C1	0.9070 (7)	0.1817 (4)	0.2310 (3)	0.0438 (10)
C2	0.8249 (7)	0.2551 (4)	0.3383 (3)	0.0477 (10)
C3	0.9350 (9)	0.2228 (5)	0.4369 (4)	0.0584 (10)
C4	1.1149 (9)	0.1232 (5)	0.4189 (4)	0.0658 (11)
H4	1.1871	0.1023	0.4831	0.079*
C5	1.1947 (10)	0.0521 (5)	0.3101 (4)	0.0717 (12)
H5	1.3189	−0.0143	0.3020	0.086*
C6	1.0896 (8)	0.0800 (4)	0.2137 (4)	0.0538 (11)
H6	1.1389	0.0326	0.1394	0.065*
C7	0.8621 (7)	0.3091 (4)	0.0861 (3)	0.0356 (8)
C8	0.5121 (7)	0.2265 (4)	−0.0728 (3)	0.0384 (9)
C9	0.3956 (8)	0.2699 (4)	−0.1700 (3)	0.0509 (10)
H9A	0.5356	0.2990	−0.2134	0.076*
H9B	0.2895	0.3476	−0.1395	0.076*
H9C	0.2864	0.1913	−0.2201	0.076*
C10	0.6334 (8)	0.3630 (5)	0.3534 (4)	0.0613 (12)
H10A	0.5392	0.3513	0.2808	0.092*
H10B	0.7265	0.4560	0.3788	0.092*
H10C	0.5097	0.3522	0.4105	0.092*
C11	0.8541 (11)	0.2953 (6)	0.5555 (4)	0.0948 (18)
H11A	0.6719	0.2654	0.5637	0.142*
H11B	0.8734	0.3962	0.5680	0.142*
H11C	0.9643	0.2713	0.6116	0.142*

	U11	U22	U33	U12	U13	U23
S1	0.0475 (6)	0.0432 (6)	0.0496 (6)	−0.0111 (4)	−0.0123 (4)	0.0231 (5)
O1	0.0659 (18)	0.0452 (16)	0.0549 (17)	−0.0173 (14)	−0.0174 (14)	0.0224 (14)
N1	0.050 (2)	0.0423 (19)	0.0379 (18)	−0.0132 (15)	−0.0127 (15)	0.0177 (15)
N2	0.0417 (18)	0.0414 (19)	0.0363 (17)	−0.0026 (15)	−0.0002 (14)	0.0210 (14)
C1	0.048 (2)	0.043 (2)	0.044 (2)	−0.0116 (19)	−0.0029 (18)	0.0217 (19)
C2	0.038 (2)	0.051 (3)	0.055 (3)	−0.0107 (19)	0.0014 (19)	0.021 (2)
C3	0.061 (3)	0.071 (3)	0.045 (2)	−0.0172 (17)	−0.0050 (19)	0.025 (2)
C4	0.071 (3)	0.072 (3)	0.064 (2)	−0.0141 (18)	−0.018 (2)	0.041 (2)
C5	0.079 (3)	0.061 (3)	0.084 (3)	0.009 (2)	−0.007 (3)	0.035 (2)
C6	0.057 (3)	0.050 (3)	0.063 (3)	0.001 (2)	−0.005 (2)	0.030 (2)
C7	0.040 (2)	0.035 (2)	0.034 (2)	0.0021 (16)	0.0001 (16)	0.0136 (17)
C8	0.041 (2)	0.038 (2)	0.036 (2)	0.0006 (18)	0.0001 (17)	0.0097 (17)
C9	0.053 (2)	0.055 (3)	0.047 (2)	−0.001 (2)	−0.0118 (19)	0.020 (2)
C10	0.060 (3)	0.068 (3)	0.052 (3)	0.002 (2)	0.010 (2)	0.012 (2)
C11	0.108 (4)	0.120 (5)	0.053 (3)	−0.017 (4)	−0.006 (3)	0.029 (3)

S1—C7	1.671 (4)	C4—H4	0.9300
O1—C8	1.221 (4)	C5—C6	1.374 (6)
N1—C7	1.316 (4)	C5—H5	0.9300
N1—C1	1.440 (4)	C6—H6	0.9300
N1—H1N	0.856 (18)	C8—C9	1.484 (5)
N2—C8	1.375 (4)	C9—H9A	0.9600
N2—C7	1.383 (4)	C9—H9B	0.9600
N2—H2N	0.838 (18)	C9—H9C	0.9600
C1—C2	1.376 (5)	C10—H10A	0.9600
C1—C6	1.391 (5)	C10—H10B	0.9600
C2—C3	1.429 (5)	C10—H10C	0.9600
C2—C10	1.470 (5)	C11—H11A	0.9600
C3—C4	1.366 (6)	C11—H11B	0.9600
C3—C11	1.481 (6)	C11—H11C	0.9600
C4—C5	1.380 (7)
C7—N1—C1	124.6 (3)	N1—C7—N2	116.9 (3)
C7—N1—H1N	115 (3)	N1—C7—S1	123.6 (3)
C1—N1—H1N	120 (3)	N2—C7—S1	119.5 (3)
C8—N2—C7	129.1 (3)	O1—C8—N2	121.9 (3)
C8—N2—H2N	113 (3)	O1—C8—C9	122.9 (3)
C7—N2—H2N	118 (3)	N2—C8—C9	115.2 (3)
C2—C1—C6	124.1 (4)	C8—C9—H9A	109.5
C2—C1—N1	118.7 (4)	C8—C9—H9B	109.5
C6—C1—N1	117.1 (4)	H9A—C9—H9B	109.5
C1—C2—C3	117.0 (4)	C8—C9—H9C	109.5
C1—C2—C10	122.6 (4)	H9A—C9—H9C	109.5
C3—C2—C10	120.4 (4)	H9B—C9—H9C	109.5
C4—C3—C2	118.4 (4)	C2—C10—H10A	109.5
C4—C3—C11	121.1 (4)	C2—C10—H10B	109.5
C2—C3—C11	120.5 (5)	H10A—C10—H10B	109.5
C3—C4—C5	123.1 (4)	C2—C10—H10C	109.5
C3—C4—H4	118.4	H10A—C10—H10C	109.5
C5—C4—H4	118.4	H10B—C10—H10C	109.5
C6—C5—C4	119.7 (5)	C3—C11—H11A	109.5
C6—C5—H5	120.2	C3—C11—H11B	109.5
C4—C5—H5	120.2	H11A—C11—H11B	109.5
C5—C6—C1	117.7 (4)	C3—C11—H11C	109.5
C5—C6—H6	121.2	H11A—C11—H11C	109.5
C1—C6—H6	121.2	H11B—C11—H11C	109.5
C7—N1—C1—C2	83.6 (5)	C11—C3—C4—C5	179.5 (4)
C7—N1—C1—C6	−99.9 (4)	C3—C4—C5—C6	−0.6 (7)
C6—C1—C2—C3	−0.4 (5)	C4—C5—C6—C1	0.8 (6)
N1—C1—C2—C3	175.8 (3)	C2—C1—C6—C5	−0.3 (6)
C6—C1—C2—C10	179.3 (3)	N1—C1—C6—C5	−176.6 (4)
N1—C1—C2—C10	−4.4 (5)	C1—N1—C7—N2	179.8 (3)
C1—C2—C3—C4	0.7 (6)	C1—N1—C7—S1	−0.1 (5)
C10—C2—C3—C4	−179.1 (4)	C8—N2—C7—N1	2.3 (6)
C1—C2—C3—C11	−179.0 (4)	C8—N2—C7—S1	−177.8 (3)
C10—C2—C3—C11	1.2 (6)	C7—N2—C8—O1	−5.1 (6)
C2—C3—C4—C5	−0.2 (7)	C7—N2—C8—C9	174.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.86 (2)	1.97 (3)	2.664 (4)	137 (3)
N1—H1N···O1i	0.86 (2)	2.50 (3)	3.168 (4)	136 (3)
N2—H2N···S1ii	0.84 (2)	2.54 (2)	3.378 (3)	176 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1	0.86 (2)	1.97 (3)	2.664 (4)	137 (3)
N1—H1N⋯O1i	0.86 (2)	2.50 (3)	3.168 (4)	136 (3)
N2—H2N⋯S1ii	0.84 (2)	2.54 (2)	3.378 (3)	176 (3)

Symmetry codes: (i) ; (ii) .