3-Acetyl-1-(2,5-dimethyl-phen-yl)thio-urea.

In the title compound, C(11)H(14)N(2)OS, the thioamide C=S and amide C=O bonds are anti to each other; the N-H bonds are also anti to each other. The mol-ecular conformation is stabilized by an N-H⋯O hydrogen bond. In the crystal, the mol-ecules are linked into inversion dimers by pairs of N-H⋯S hydrogen bonds.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Gowda et al. (2001 ▶); Kumar et al. (2012 ▶); Shahwar et al. (2012 ▶), of N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007 ▶) and of N-chloro­aryl­sulfonamides, see: Gowda & Ramachandra (1989 ▶); Shetty & Gowda (2004 ▶).

Experimental

Crystal data

C11H14N2OS

M = 222.30

Triclinic,

a = 5.0312 (2) Å

b = 10.9329 (6) Å

c = 11.0568 (7) Å

α = 105.711 (5)°

β = 100.020 (5)°

γ = 93.037 (4)°

V = 573.31 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 293 K

0.42 × 0.38 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.899, T max = 0.950

3641 measured reflections

2344 independent reflections

2068 reflections with I > 2σ(I)

R int = 0.007

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.101

S = 1.05

2344 reflections

145 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.20 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/S1600536812029601/bt5960sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029601/bt5960Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812029601/bt5960Isup3.cml

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

C11H14N2OS	Z = 2
Mr = 222.30	F(000) = 236
Triclinic, P1	Dx = 1.288 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.0312 (2) Å	Cell parameters from 2369 reflections
b = 10.9329 (6) Å	θ = 3.1–27.7°
c = 11.0568 (7) Å	µ = 0.26 mm−1
α = 105.711 (5)°	T = 293 K
β = 100.020 (5)°	Prism, colourless
γ = 93.037 (4)°	0.42 × 0.38 × 0.20 mm
V = 573.31 (6) Å3

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2344 independent reflections
Radiation source: fine-focus sealed tube	2068 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.007
Rotation method data acquisition using ω and phi scans	θmax = 26.4°, θmin = 3.1°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −5→6
Tmin = 0.899, Tmax = 0.950	k = −11→13
3641 measured reflections	l = −13→13

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0459P)2 + 0.2328P] where P = (Fo2 + 2Fc2)/3
2344 reflections	(Δ/σ)max = 0.001
145 parameters	Δρmax = 0.23 e Å−3
2 restraints	Δρmin = −0.20 e Å−3

Experimental. 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
C1	0.6145 (3)	0.73651 (15)	0.28289 (15)	0.0372 (4)
C2	0.6492 (3)	0.61308 (15)	0.21687 (15)	0.0377 (4)
C3	0.5232 (4)	0.51510 (16)	0.25210 (17)	0.0439 (4)
H3	0.5400	0.4308	0.2096	0.053*
C4	0.3747 (4)	0.53925 (17)	0.34786 (17)	0.0458 (4)
H4	0.2947	0.4711	0.3688	0.055*
C5	0.3422 (3)	0.66295 (17)	0.41356 (16)	0.0416 (4)
C6	0.4659 (3)	0.76177 (16)	0.37962 (16)	0.0412 (4)
H6	0.4489	0.8460	0.4223	0.049*
C7	0.6584 (3)	0.89287 (15)	0.16443 (16)	0.0366 (3)
C8	1.0446 (4)	1.06364 (16)	0.24317 (18)	0.0442 (4)
C9	1.1609 (4)	1.17630 (19)	0.2102 (2)	0.0571 (5)
H9A	1.0190	1.2277	0.1915	0.069*
H9B	1.2423	1.1473	0.1365	0.069*
H9C	1.2962	1.2263	0.2813	0.069*
C10	0.8130 (4)	0.58529 (19)	0.11363 (18)	0.0491 (4)
H10A	0.9914	0.6302	0.1463	0.059*
H10B	0.7259	0.6127	0.0425	0.059*
H10C	0.8268	0.4951	0.0859	0.059*
C11	0.1781 (4)	0.6891 (2)	0.5173 (2)	0.0587 (5)
H11A	0.2316	0.6389	0.5748	0.070*
H11B	−0.0111	0.6668	0.4797	0.070*
H11C	0.2089	0.7781	0.5638	0.070*
N1	0.7489 (3)	0.84398 (14)	0.25857 (15)	0.0438 (4)
H1N	0.895 (3)	0.8817 (18)	0.3093 (18)	0.053*
N2	0.8099 (3)	1.00118 (13)	0.16102 (15)	0.0401 (3)
H2N	0.751 (4)	1.0323 (18)	0.1002 (17)	0.048*
O1	1.1487 (3)	1.03056 (13)	0.33502 (14)	0.0603 (4)
S1	0.37879 (9)	0.83331 (4)	0.05301 (4)	0.04690 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0373 (8)	0.0377 (8)	0.0365 (8)	0.0001 (6)	−0.0019 (6)	0.0171 (7)
C2	0.0372 (8)	0.0410 (9)	0.0350 (8)	0.0040 (7)	0.0017 (6)	0.0144 (7)
C3	0.0538 (10)	0.0346 (8)	0.0432 (9)	0.0047 (7)	0.0056 (8)	0.0130 (7)
C4	0.0507 (10)	0.0440 (9)	0.0473 (10)	−0.0005 (8)	0.0075 (8)	0.0229 (8)
C5	0.0399 (9)	0.0522 (10)	0.0353 (8)	0.0072 (7)	0.0031 (7)	0.0189 (7)
C6	0.0457 (9)	0.0378 (8)	0.0376 (9)	0.0091 (7)	0.0003 (7)	0.0105 (7)
C7	0.0362 (8)	0.0345 (8)	0.0414 (9)	0.0029 (6)	0.0082 (7)	0.0143 (7)
C8	0.0419 (9)	0.0344 (8)	0.0515 (10)	−0.0002 (7)	0.0051 (8)	0.0077 (7)
C9	0.0523 (11)	0.0441 (10)	0.0693 (13)	−0.0127 (8)	0.0051 (9)	0.0144 (9)
C10	0.0482 (10)	0.0552 (11)	0.0459 (10)	0.0076 (8)	0.0112 (8)	0.0161 (8)
C11	0.0547 (11)	0.0795 (14)	0.0489 (11)	0.0162 (10)	0.0157 (9)	0.0248 (10)
N1	0.0429 (8)	0.0393 (8)	0.0466 (8)	−0.0065 (6)	−0.0055 (6)	0.0191 (6)
N2	0.0376 (7)	0.0360 (7)	0.0477 (8)	−0.0014 (6)	0.0024 (6)	0.0183 (6)
O1	0.0610 (8)	0.0489 (8)	0.0598 (9)	−0.0096 (6)	−0.0144 (7)	0.0165 (6)
S1	0.0406 (2)	0.0483 (3)	0.0527 (3)	−0.00880 (18)	−0.00441 (19)	0.0269 (2)

C1—C6	1.385 (2)	C8—O1	1.213 (2)
C1—C2	1.386 (2)	C8—N2	1.375 (2)
C1—N1	1.436 (2)	C8—C9	1.495 (2)
C2—C3	1.393 (2)	C9—H9A	0.9600
C2—C10	1.497 (2)	C9—H9B	0.9600
C3—C4	1.376 (3)	C9—H9C	0.9600
C3—H3	0.9300	C10—H10A	0.9600
C4—C5	1.384 (3)	C10—H10B	0.9600
C4—H4	0.9300	C10—H10C	0.9600
C5—C6	1.388 (2)	C11—H11A	0.9600
C5—C11	1.502 (3)	C11—H11B	0.9600
C6—H6	0.9300	C11—H11C	0.9600
C7—N1	1.319 (2)	N1—H1N	0.852 (15)
C7—N2	1.387 (2)	N2—H2N	0.849 (15)
C7—S1	1.6692 (17)
C6—C1—C2	122.16 (15)	C8—C9—H9A	109.5
C6—C1—N1	117.34 (15)	C8—C9—H9B	109.5
C2—C1—N1	120.37 (15)	H9A—C9—H9B	109.5
C1—C2—C3	116.24 (15)	C8—C9—H9C	109.5
C1—C2—C10	122.39 (15)	H9A—C9—H9C	109.5
C3—C2—C10	121.37 (16)	H9B—C9—H9C	109.5
C4—C3—C2	122.01 (16)	C2—C10—H10A	109.5
C4—C3—H3	119.0	C2—C10—H10B	109.5
C2—C3—H3	119.0	H10A—C10—H10B	109.5
C3—C4—C5	121.29 (16)	C2—C10—H10C	109.5
C3—C4—H4	119.4	H10A—C10—H10C	109.5
C5—C4—H4	119.4	H10B—C10—H10C	109.5
C4—C5—C6	117.50 (16)	C5—C11—H11A	109.5
C4—C5—C11	121.20 (17)	C5—C11—H11B	109.5
C6—C5—C11	121.31 (17)	H11A—C11—H11B	109.5
C1—C6—C5	120.80 (15)	C5—C11—H11C	109.5
C1—C6—H6	119.6	H11A—C11—H11C	109.5
C5—C6—H6	119.6	H11B—C11—H11C	109.5
N1—C7—N2	116.17 (15)	C7—N1—C1	124.80 (14)
N1—C7—S1	124.34 (12)	C7—N1—H1N	116.3 (14)
N2—C7—S1	119.49 (12)	C1—N1—H1N	118.9 (14)
O1—C8—N2	122.97 (16)	C8—N2—C7	128.05 (15)
O1—C8—C9	122.62 (17)	C8—N2—H2N	116.1 (14)
N2—C8—C9	114.41 (16)	C7—N2—H2N	115.9 (14)
C6—C1—C2—C3	0.7 (2)	C4—C5—C6—C1	0.4 (2)
N1—C1—C2—C3	176.46 (14)	C11—C5—C6—C1	−179.34 (16)
C6—C1—C2—C10	−179.04 (16)	N2—C7—N1—C1	176.57 (15)
N1—C1—C2—C10	−3.3 (2)	S1—C7—N1—C1	−3.1 (3)
C1—C2—C3—C4	−0.6 (3)	C6—C1—N1—C7	−100.6 (2)
C10—C2—C3—C4	179.20 (17)	C2—C1—N1—C7	83.4 (2)
C2—C3—C4—C5	0.4 (3)	O1—C8—N2—C7	−1.7 (3)
C3—C4—C5—C6	−0.3 (3)	C9—C8—N2—C7	178.47 (17)
C3—C4—C5—C11	179.49 (17)	N1—C7—N2—C8	0.6 (3)
C2—C1—C6—C5	−0.7 (2)	S1—C7—N2—C8	−179.70 (14)
N1—C1—C6—C5	−176.52 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.85 (2)	1.94 (2)	2.6382 (19)	139 (2)
N2—H2N···S1i	0.85 (2)	2.55 (2)	3.3904 (15)	169 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1	0.85 (2)	1.94 (2)	2.6382 (19)	139 (2)
N2—H2N⋯S1i	0.85 (2)	2.55 (2)	3.3904 (15)	169 (2)

Symmetry code: (i) .