3-Acetyl-1-(2,4-dimethyl-phen-yl)thio-urea.

In the crystal structure of the title compound, C(11)H(14)N(2)OS, the two N-H bonds are anti to each other. There is an intramolecular N-H⋯O hydrogen bond generating an S(6) ring motif.In the crystal, mol-ecules are linked via N-H⋯S hydrogen bonds with an R(2) (2)(8) motif and N-H⋯O hydrogen bonds with an R(2) (2)(12) motif into chains running along [1-10].

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 = 5.0510 (7) Å

b = 9.973 (1) Å

c = 12.503 (2) Å

α = 69.15 (1)°

β = 89.43 (1)°

γ = 84.07 (1)°

V = 585.18 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.25 mm−1

T = 293 K

0.44 × 0.44 × 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 = 0.897, T max = 0.951

3701 measured reflections

2393 independent reflections

2094 reflections with I > 2σ(I)

R int = 0.008

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.097

S = 1.07

2393 reflections

145 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.19 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/S1600536812032382/bt5977sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032382/bt5977Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812032382/bt5977Isup3.cml

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

C11H14N2OS	Z = 2
Mr = 222.30	F(000) = 236
Triclinic, P1	Dx = 1.262 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.0510 (7) Å	Cell parameters from 2430 reflections
b = 9.973 (1) Å	θ = 3.3–27.8°
c = 12.503 (2) Å	µ = 0.25 mm−1
α = 69.15 (1)°	T = 293 K
β = 89.43 (1)°	Prism, colourless
γ = 84.07 (1)°	0.44 × 0.44 × 0.20 mm
V = 585.18 (14) Å3

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2393 independent reflections
Radiation source: fine-focus sealed tube	2094 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.008
Rotation method data acquisition using ω and phi scans.	θmax = 26.4°, θmin = 3.3°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −6→6
Tmin = 0.897, Tmax = 0.951	k = −12→12
3701 measured reflections	l = −14→15

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) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0402P)2 + 0.2499P] where P = (Fo2 + 2Fc2)/3
2393 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.20 e Å−3
2 restraints	Δρmin = −0.19 e Å−3

Experimental. Abosrption 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	1.11565 (9)	0.05240 (5)	0.14186 (4)	0.04794 (16)
O1	0.4331 (3)	0.38737 (13)	−0.04561 (11)	0.0535 (4)
N1	0.7972 (3)	0.28872 (14)	0.12507 (11)	0.0372 (3)
H1N	0.676 (3)	0.3551 (19)	0.0874 (15)	0.045*
N2	0.7355 (3)	0.19052 (15)	−0.01371 (11)	0.0368 (3)
H2N	0.785 (4)	0.1221 (18)	−0.0360 (16)	0.044*
C1	0.9086 (3)	0.29552 (17)	0.22808 (13)	0.0371 (4)
C2	0.8314 (3)	0.20597 (19)	0.33431 (14)	0.0418 (4)
C3	0.9404 (4)	0.2218 (2)	0.43090 (16)	0.0528 (5)
H3	0.8925	0.1627	0.5030	0.063*
C4	1.1165 (4)	0.3217 (2)	0.42369 (18)	0.0578 (5)
C5	1.1864 (5)	0.4092 (2)	0.3166 (2)	0.0620 (6)
H5	1.3043	0.4772	0.3101	0.074*
C6	1.0835 (4)	0.39718 (19)	0.21850 (17)	0.0494 (4)
H6	1.1315	0.4570	0.1467	0.059*
C7	0.8707 (3)	0.18561 (16)	0.08396 (13)	0.0337 (3)
C8	0.5208 (3)	0.28452 (17)	−0.07079 (13)	0.0383 (4)
C9	0.4051 (4)	0.2509 (2)	−0.16736 (16)	0.0524 (5)
H9A	0.3200	0.1639	−0.1369	0.079*
H9B	0.5448	0.2382	−0.2166	0.079*
H9C	0.2767	0.3291	−0.2103	0.079*
C10	0.6410 (4)	0.0967 (2)	0.34550 (17)	0.0568 (5)
H10A	0.7238	0.0220	0.3208	0.085*
H10B	0.4841	0.1426	0.2989	0.085*
H10C	0.5928	0.0553	0.4240	0.085*
C11	1.2348 (6)	0.3306 (3)	0.5323 (2)	0.0884 (9)
H11A	1.4040	0.2730	0.5507	0.133*
H11B	1.1165	0.2952	0.5943	0.133*
H11C	1.2583	0.4291	0.5203	0.133*

	U11	U22	U33	U12	U13	U23
S1	0.0495 (3)	0.0487 (3)	0.0531 (3)	0.01791 (19)	−0.0211 (2)	−0.0330 (2)
O1	0.0681 (8)	0.0424 (7)	0.0520 (7)	0.0189 (6)	−0.0248 (6)	−0.0253 (6)
N1	0.0456 (8)	0.0348 (7)	0.0329 (7)	0.0092 (6)	−0.0116 (6)	−0.0174 (6)
N2	0.0423 (7)	0.0373 (7)	0.0362 (7)	0.0055 (6)	−0.0082 (6)	−0.0222 (6)
C1	0.0430 (9)	0.0359 (8)	0.0359 (8)	0.0103 (7)	−0.0104 (7)	−0.0205 (7)
C2	0.0411 (9)	0.0480 (9)	0.0375 (9)	0.0084 (7)	−0.0061 (7)	−0.0203 (7)
C3	0.0572 (11)	0.0653 (12)	0.0359 (9)	0.0138 (9)	−0.0089 (8)	−0.0233 (9)
C4	0.0681 (12)	0.0603 (12)	0.0554 (12)	0.0191 (10)	−0.0265 (10)	−0.0398 (10)
C5	0.0752 (14)	0.0469 (11)	0.0726 (14)	−0.0021 (10)	−0.0257 (11)	−0.0323 (10)
C6	0.0624 (11)	0.0386 (9)	0.0501 (10)	−0.0018 (8)	−0.0110 (8)	−0.0199 (8)
C7	0.0362 (8)	0.0341 (8)	0.0334 (8)	−0.0004 (6)	−0.0032 (6)	−0.0162 (6)
C8	0.0452 (9)	0.0359 (8)	0.0337 (8)	0.0014 (7)	−0.0081 (7)	−0.0137 (7)
C9	0.0600 (11)	0.0536 (11)	0.0476 (10)	0.0087 (9)	−0.0224 (9)	−0.0262 (9)
C10	0.0529 (11)	0.0671 (13)	0.0461 (10)	−0.0090 (10)	0.0012 (8)	−0.0144 (9)
C11	0.114 (2)	0.0906 (18)	0.0769 (16)	0.0238 (16)	−0.0485 (15)	−0.0576 (15)

S1—C7	1.6774 (16)	C4—C11	1.524 (3)
O1—C8	1.217 (2)	C5—C6	1.385 (3)
N1—C7	1.3239 (19)	C5—H5	0.9300
N1—C1	1.4369 (19)	C6—H6	0.9300
N1—H1N	0.856 (14)	C8—C9	1.502 (2)
N2—C8	1.376 (2)	C9—H9A	0.9600
N2—C7	1.3883 (19)	C9—H9B	0.9600
N2—H2N	0.840 (14)	C9—H9C	0.9600
C1—C6	1.385 (2)	C10—H10A	0.9600
C1—C2	1.390 (2)	C10—H10B	0.9600
C2—C3	1.398 (2)	C10—H10C	0.9600
C2—C10	1.496 (3)	C11—H11A	0.9600
C3—C4	1.382 (3)	C11—H11B	0.9600
C3—H3	0.9300	C11—H11C	0.9600
C4—C5	1.379 (3)
C7—N1—C1	123.94 (13)	N1—C7—N2	117.04 (13)
C7—N1—H1N	117.4 (13)	N1—C7—S1	124.11 (12)
C1—N1—H1N	118.6 (13)	N2—C7—S1	118.86 (11)
C8—N2—C7	128.32 (13)	O1—C8—N2	122.67 (14)
C8—N2—H2N	117.3 (13)	O1—C8—C9	122.70 (15)
C7—N2—H2N	114.1 (13)	N2—C8—C9	114.64 (14)
C6—C1—C2	121.37 (15)	C8—C9—H9A	109.5
C6—C1—N1	118.48 (15)	C8—C9—H9B	109.5
C2—C1—N1	120.09 (15)	H9A—C9—H9B	109.5
C1—C2—C3	117.08 (17)	C8—C9—H9C	109.5
C1—C2—C10	121.75 (15)	H9A—C9—H9C	109.5
C3—C2—C10	121.17 (17)	H9B—C9—H9C	109.5
C4—C3—C2	122.68 (19)	C2—C10—H10A	109.5
C4—C3—H3	118.7	C2—C10—H10B	109.5
C2—C3—H3	118.7	H10A—C10—H10B	109.5
C5—C4—C3	118.36 (17)	C2—C10—H10C	109.5
C5—C4—C11	121.5 (2)	H10A—C10—H10C	109.5
C3—C4—C11	120.1 (2)	H10B—C10—H10C	109.5
C4—C5—C6	120.95 (19)	C4—C11—H11A	109.5
C4—C5—H5	119.5	C4—C11—H11B	109.5
C6—C5—H5	119.5	H11A—C11—H11B	109.5
C5—C6—C1	119.55 (19)	C4—C11—H11C	109.5
C5—C6—H6	120.2	H11A—C11—H11C	109.5
C1—C6—H6	120.2	H11B—C11—H11C	109.5
C7—N1—C1—C6	105.91 (19)	C11—C4—C5—C6	178.1 (2)
C7—N1—C1—C2	−77.0 (2)	C4—C5—C6—C1	−0.2 (3)
C6—C1—C2—C3	−0.8 (2)	C2—C1—C6—C5	0.7 (3)
N1—C1—C2—C3	−177.78 (14)	N1—C1—C6—C5	177.79 (16)
C6—C1—C2—C10	179.50 (17)	C1—N1—C7—N2	177.11 (15)
N1—C1—C2—C10	2.5 (2)	C1—N1—C7—S1	−3.4 (2)
C1—C2—C3—C4	0.3 (3)	C8—N2—C7—N1	−4.4 (3)
C10—C2—C3—C4	−179.90 (17)	C8—N2—C7—S1	176.05 (14)
C2—C3—C4—C5	0.1 (3)	C7—N2—C8—O1	6.3 (3)
C2—C3—C4—C11	−178.16 (18)	C7—N2—C8—C9	−174.26 (16)
C3—C4—C5—C6	−0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.86 (1)	1.99 (2)	2.6673 (18)	135 (2)
N1—H1N···O1i	0.86 (2)	2.44 (2)	3.121 (2)	137 (2)
N2—H2N···S1ii	0.84 (1)	2.55 (2)	3.3711 (14)	168 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1	0.86 (1)	1.99 (2)	2.6673 (18)	135 (2)
N1—H1N⋯O1i	0.86 (2)	2.44 (2)	3.121 (2)	137 (2)
N2—H2N⋯S1ii	0.84 (1)	2.55 (2)	3.3711 (14)	168 (2)

Symmetry codes: (i) ; (ii) .