3-Acetyl-1-(2,6-dimethyl-phen-yl)thio-urea.

In the title compound, C(11)H(14)N(2)OS, the two N-H bonds are anti to each other and one of them is anti to the C=S and the other is syn. Further, the amide C=S and the C=O groups are anti to each other. The dihedral angle between the benzene ring and the side chain is 83.74 (5)°. An intra-molecular N-H⋯O hydrogen bond occurs. In the crystal, mol-ecules are linked into inversion dimers by pairs of N-H⋯S inter-actions.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Gowda et al. (2006 ▶); Shahwar et al. (2012 ▶), of N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007 ▶) and of N-chloro­aryl­sulfonamides, see: Gowda et al. (2005 ▶); Shetty & Gowda (2004 ▶).

Experimental

Crystal data

C11H14N2OS

M = 222.31

Triclinic,

a = 8.008 (1) Å

b = 8.211 (1) Å

c = 10.037 (1) Å

α = 89.39 (1)°

β = 77.65 (1)°

γ = 64.71 (1)°

V = 580.47 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 295 K

0.30 × 0.20 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur Sapphire CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.928, T max = 0.980

3904 measured reflections

2362 independent reflections

1858 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.115

S = 1.06

2362 reflections

145 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.31 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/S1600536812029248/rk2369sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029248/rk2369Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812029248/rk2369Isup3.cml

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

C11H14N2OS	Z = 2
Mr = 222.31	F(000) = 236
Triclinic, P1	Dx = 1.272 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.008 (1) Å	Cell parameters from 1747 reflections
b = 8.211 (1) Å	θ = 2.8–27.6°
c = 10.037 (1) Å	µ = 0.26 mm−1
α = 89.39 (1)°	T = 295 K
β = 77.65 (1)°	Prism, light yellow
γ = 64.71 (1)°	0.30 × 0.20 × 0.08 mm
V = 580.47 (13) Å3

Oxford Diffraction Xcalibur Sapphire CCD diffractometer	2362 independent reflections
Radiation source: fine-focus sealed tube	1858 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.012
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 2.8°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −9→6
Tmin = 0.928, Tmax = 0.980	k = −10→10
3904 measured reflections	l = −12→9

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0515P)2 + 0.2097P] where P = (Fo2 + 2Fc2)/3
2362 reflections	(Δ/σ)max = 0.016
145 parameters	Δρmax = 0.21 e Å−3
2 restraints	Δρmin = −0.31 e Å−3

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
C1	0.0904 (2)	0.0786 (2)	0.13742 (17)	0.0388 (4)
C2	0.1028 (3)	−0.0846 (3)	0.1866 (2)	0.0467 (5)
C3	0.2402 (3)	−0.2433 (3)	0.1110 (2)	0.0583 (6)
H3	0.2520	−0.3542	0.1415	0.070*
C4	0.3592 (3)	−0.2388 (3)	−0.0087 (2)	0.0605 (6)
H4	0.4507	−0.3463	−0.0584	0.073*
C5	0.3434 (3)	−0.0761 (3)	−0.0552 (2)	0.0553 (6)
H5	0.4246	−0.0751	−0.1364	0.066*
C6	0.2081 (3)	0.0875 (3)	0.01660 (19)	0.0441 (4)
C7	−0.0262 (2)	0.3365 (2)	0.30688 (17)	0.0401 (4)
C8	−0.3639 (3)	0.5655 (3)	0.35392 (19)	0.0476 (5)
C9	−0.4949 (3)	0.7457 (3)	0.4319 (3)	0.0671 (7)
H9A	−0.4325	0.8237	0.4212	0.080*
H9B	−0.5285	0.7297	0.5272	0.080*
H9C	−0.6077	0.7989	0.3972	0.080*
C10	−0.0265 (4)	−0.0907 (4)	0.3167 (3)	0.0736 (7)
H10A	−0.1540	−0.0437	0.3048	0.088*
H10B	−0.0218	−0.0189	0.3894	0.088*
H10C	0.0136	−0.2135	0.3393	0.088*
C11	0.1920 (3)	0.2635 (3)	−0.0344 (2)	0.0621 (6)
H11A	0.1901	0.3396	0.0385	0.075*
H11B	0.0768	0.3217	−0.0656	0.075*
H11C	0.2987	0.2425	−0.1087	0.075*
N1	−0.0546 (2)	0.2439 (2)	0.21360 (16)	0.0434 (4)
H1N	−0.166 (2)	0.286 (3)	0.203 (2)	0.052*
N2	−0.1819 (2)	0.4932 (2)	0.37213 (16)	0.0446 (4)
H2N	−0.158 (3)	0.546 (3)	0.4329 (19)	0.054*
O1	−0.4147 (2)	0.4896 (2)	0.27946 (18)	0.0697 (5)
S1	0.18238 (7)	0.27758 (8)	0.34744 (6)	0.0605 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0349 (9)	0.0356 (9)	0.0395 (9)	−0.0070 (7)	−0.0135 (7)	−0.0102 (7)
C2	0.0511 (11)	0.0436 (11)	0.0458 (10)	−0.0171 (9)	−0.0189 (8)	−0.0028 (8)
C3	0.0619 (13)	0.0365 (11)	0.0731 (14)	−0.0107 (10)	−0.0315 (12)	−0.0045 (10)
C4	0.0471 (11)	0.0438 (12)	0.0716 (15)	0.0030 (9)	−0.0233 (11)	−0.0238 (10)
C5	0.0383 (10)	0.0656 (14)	0.0449 (11)	−0.0080 (9)	−0.0061 (8)	−0.0163 (10)
C6	0.0399 (9)	0.0452 (10)	0.0420 (10)	−0.0120 (8)	−0.0129 (8)	−0.0060 (8)
C7	0.0387 (9)	0.0384 (9)	0.0366 (9)	−0.0122 (8)	−0.0048 (7)	−0.0075 (7)
C8	0.0425 (10)	0.0437 (11)	0.0444 (10)	−0.0086 (8)	−0.0068 (8)	−0.0076 (8)
C9	0.0521 (12)	0.0519 (13)	0.0708 (15)	0.0008 (10)	−0.0109 (11)	−0.0173 (11)
C10	0.0924 (19)	0.0756 (17)	0.0596 (14)	−0.0442 (15)	−0.0147 (13)	0.0097 (12)
C11	0.0633 (14)	0.0621 (14)	0.0605 (13)	−0.0273 (11)	−0.0133 (11)	0.0067 (11)
N1	0.0352 (8)	0.0397 (9)	0.0463 (9)	−0.0069 (7)	−0.0106 (7)	−0.0145 (7)
N2	0.0404 (8)	0.0405 (8)	0.0437 (9)	−0.0100 (7)	−0.0068 (7)	−0.0148 (7)
O1	0.0475 (8)	0.0647 (10)	0.0810 (11)	−0.0048 (7)	−0.0238 (8)	−0.0261 (8)
S1	0.0389 (3)	0.0689 (4)	0.0590 (3)	−0.0087 (2)	−0.0118 (2)	−0.0315 (3)

C1—C6	1.390 (3)	C8—O1	1.212 (2)
C1—C2	1.394 (3)	C8—N2	1.372 (3)
C1—N1	1.439 (2)	C8—C9	1.500 (3)
C2—C3	1.387 (3)	C9—H9A	0.9600
C2—C10	1.498 (3)	C9—H9B	0.9600
C3—C4	1.376 (3)	C9—H9C	0.9600
C3—H3	0.9300	C10—H10A	0.9600
C4—C5	1.373 (3)	C10—H10B	0.9600
C4—H4	0.9300	C10—H10C	0.9600
C5—C6	1.393 (3)	C11—H11A	0.9600
C5—H5	0.9300	C11—H11B	0.9600
C6—C11	1.490 (3)	C11—H11C	0.9600
C7—N1	1.327 (2)	N1—H1N	0.839 (15)
C7—N2	1.392 (2)	N2—H2N	0.848 (15)
C7—S1	1.6694 (19)
C6—C1—C2	122.75 (16)	C8—C9—H9A	109.5
C6—C1—N1	119.14 (17)	C8—C9—H9B	109.5
C2—C1—N1	118.08 (16)	H9A—C9—H9B	109.5
C3—C2—C1	117.73 (19)	C8—C9—H9C	109.5
C3—C2—C10	120.5 (2)	H9A—C9—H9C	109.5
C1—C2—C10	121.76 (18)	H9B—C9—H9C	109.5
C4—C3—C2	120.8 (2)	C2—C10—H10A	109.5
C4—C3—H3	119.6	C2—C10—H10B	109.5
C2—C3—H3	119.6	H10A—C10—H10B	109.5
C5—C4—C3	120.25 (18)	C2—C10—H10C	109.5
C5—C4—H4	119.9	H10A—C10—H10C	109.5
C3—C4—H4	119.9	H10B—C10—H10C	109.5
C4—C5—C6	121.4 (2)	C6—C11—H11A	109.5
C4—C5—H5	119.3	C6—C11—H11B	109.5
C6—C5—H5	119.3	H11A—C11—H11B	109.5
C1—C6—C5	117.06 (19)	C6—C11—H11C	109.5
C1—C6—C11	121.87 (17)	H11A—C11—H11C	109.5
C5—C6—C11	121.07 (19)	H11B—C11—H11C	109.5
N1—C7—N2	116.66 (16)	C7—N1—C1	123.82 (15)
N1—C7—S1	124.10 (13)	C7—N1—H1N	115.6 (15)
N2—C7—S1	119.24 (13)	C1—N1—H1N	120.5 (15)
O1—C8—N2	122.32 (17)	C8—N2—C7	128.57 (16)
O1—C8—C9	122.46 (19)	C8—N2—H2N	118.1 (15)
N2—C8—C9	115.22 (18)	C7—N2—H2N	113.3 (15)
C6—C1—C2—C3	0.5 (3)	N1—C1—C6—C11	1.8 (3)
N1—C1—C2—C3	178.56 (16)	C4—C5—C6—C1	0.2 (3)
C6—C1—C2—C10	−179.58 (19)	C4—C5—C6—C11	179.9 (2)
N1—C1—C2—C10	−1.5 (3)	N2—C7—N1—C1	−179.56 (17)
C1—C2—C3—C4	−0.2 (3)	S1—C7—N1—C1	1.3 (3)
C10—C2—C3—C4	179.9 (2)	C6—C1—N1—C7	−87.1 (2)
C2—C3—C4—C5	−0.1 (3)	C2—C1—N1—C7	94.8 (2)
C3—C4—C5—C6	0.1 (3)	O1—C8—N2—C7	4.7 (3)
C2—C1—C6—C5	−0.5 (3)	C9—C8—N2—C7	−174.9 (2)
N1—C1—C6—C5	−178.51 (15)	N1—C7—N2—C8	0.6 (3)
C2—C1—C6—C11	179.82 (18)	S1—C7—N2—C8	179.79 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.84 (2)	1.97 (2)	2.658 (2)	138 (2)
N2—H2N···S1i	0.85 (2)	2.58 (2)	3.4012 (16)	164 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1	0.84 (2)	1.97 (2)	2.658 (2)	138 (2)
N2—H2N⋯S1i	0.85 (2)	2.58 (2)	3.4012 (16)	164 (2)

Symmetry code: (i) .