3-Acetyl-1-(3-chloro-phen-yl)thio-urea.

In the title compound, C(9)H(9)ClN(2)OS, the 3-chloro-phenyl and acetyl-thio-urea fragments are oriented at a dihedral angle of 62.68 (5)°. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif. Mol-ecules are linked into dimers via a cyclic R(2) (2)(8) motif of N-H⋯S hydrogen bonds. These dimers are further connected through C-H⋯S inter-actions, completing an R(2) (2)(12) motif, into chains along [010].

Related literature

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

Experimental

Crystal data

C9H9ClN2OS

M = 228.69

Monoclinic,

a = 28.3980 (14) Å

b = 4.1768 (2) Å

c = 20.2635 (11) Å

β = 122.651 (2)°

V = 2023.69 (18) Å3

Z = 8

Mo Kα radiation

μ = 0.55 mm−1

T = 296 K

0.35 × 0.22 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.868, T max = 0.872

7045 measured reflections

1775 independent reflections

1450 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.109

S = 1.11

1775 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.23 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/S1600536812012147/gk2470sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012147/gk2470Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812012147/gk2470Isup3.cml

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

C9H9ClN2OS	F(000) = 944
Mr = 228.69	Dx = 1.501 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1464 reflections
a = 28.3980 (14) Å	θ = 2.1–25.1°
b = 4.1768 (2) Å	µ = 0.55 mm−1
c = 20.2635 (11) Å	T = 296 K
β = 122.651 (2)°	Rod, colorless
V = 2023.69 (18) Å3	0.35 × 0.22 × 0.22 mm
Z = 8

Bruker Kappa APEXII CCD diffractometer	1745 independent reflections
Radiation source: fine-focus sealed tube	1450 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
Detector resolution: 8.10 pixels mm-1	θmax = 25.1°, θmin = 2.1°
ω scans	h = −33→27
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −4→3
Tmin = 0.868, Tmax = 0.872	l = −19→24
7045 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0527P)2 + 1.9073P] where P = (Fo2 + 2Fc2)/3
1775 reflections	(Δ/σ)max < 0.001
128 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.23 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
Cl1	0.27943 (3)	0.9289 (2)	0.34233 (4)	0.0593 (3)
S1	0.08011 (2)	0.46913 (17)	0.10724 (3)	0.0436 (2)
O1	−0.03091 (7)	1.0496 (5)	0.16023 (11)	0.0610 (7)
N1	0.06728 (7)	0.7792 (5)	0.21108 (10)	0.0383 (6)
N2	−0.00930 (7)	0.7704 (5)	0.08375 (10)	0.0353 (6)
C1	0.12315 (9)	0.7158 (6)	0.27507 (12)	0.0334 (7)
C2	0.16843 (9)	0.8388 (6)	0.27522 (13)	0.0375 (8)
C3	0.22127 (9)	0.7785 (6)	0.33950 (13)	0.0375 (7)
C4	0.22942 (10)	0.6054 (7)	0.40248 (14)	0.0461 (8)
C5	0.18373 (11)	0.4900 (7)	0.40138 (16)	0.0520 (9)
C6	0.13025 (10)	0.5409 (6)	0.33725 (14)	0.0422 (8)
C7	0.04606 (9)	0.6845 (5)	0.13794 (12)	0.0328 (7)
C8	−0.04474 (9)	0.9441 (6)	0.09596 (14)	0.0395 (8)
C9	−0.10196 (10)	0.9910 (7)	0.02487 (15)	0.0480 (9)
H1	0.04591	0.88682	0.22087	0.0459*
H2	−0.02292	0.70566	0.03650	0.0424*
H3	0.16340	0.95861	0.23319	0.0450*
H4	0.26537	0.56692	0.44526	0.0553*
H5	0.18883	0.37642	0.44424	0.0624*
H6	0.09947	0.45780	0.33622	0.0506*
H9A	−0.09942	1.10785	−0.01390	0.0720*
H9B	−0.12438	1.10907	0.03877	0.0720*
H9C	−0.11887	0.78623	0.00402	0.0720*

	U11	U22	U33	U12	U13	U23
Cl1	0.0285 (4)	0.0836 (6)	0.0561 (5)	−0.0088 (3)	0.0164 (3)	0.0058 (4)
S1	0.0301 (4)	0.0600 (4)	0.0331 (4)	0.0091 (3)	0.0120 (3)	−0.0070 (3)
O1	0.0378 (11)	0.0981 (16)	0.0396 (11)	0.0147 (10)	0.0159 (9)	−0.0173 (10)
N1	0.0223 (10)	0.0590 (13)	0.0290 (10)	0.0031 (9)	0.0109 (8)	−0.0061 (9)
N2	0.0231 (9)	0.0509 (12)	0.0251 (10)	0.0023 (8)	0.0086 (8)	−0.0049 (8)
C1	0.0248 (11)	0.0434 (13)	0.0262 (12)	0.0014 (9)	0.0099 (9)	−0.0051 (9)
C2	0.0303 (13)	0.0479 (14)	0.0283 (12)	−0.0001 (10)	0.0119 (10)	0.0032 (10)
C3	0.0250 (12)	0.0480 (14)	0.0334 (12)	−0.0038 (10)	0.0117 (10)	−0.0051 (10)
C4	0.0302 (13)	0.0605 (16)	0.0342 (14)	0.0060 (11)	0.0085 (11)	0.0070 (12)
C5	0.0439 (16)	0.0684 (18)	0.0374 (14)	0.0033 (13)	0.0178 (13)	0.0173 (13)
C6	0.0340 (14)	0.0545 (15)	0.0383 (14)	−0.0041 (11)	0.0196 (11)	0.0004 (11)
C7	0.0242 (12)	0.0400 (13)	0.0298 (12)	−0.0014 (9)	0.0116 (10)	−0.0003 (10)
C8	0.0274 (13)	0.0504 (15)	0.0371 (14)	0.0019 (10)	0.0150 (11)	−0.0017 (11)
C9	0.0304 (14)	0.0653 (17)	0.0412 (14)	0.0124 (12)	0.0146 (12)	−0.0002 (12)

Cl1—C3	1.739 (3)	C3—C4	1.373 (4)
S1—C7	1.667 (3)	C4—C5	1.373 (5)
O1—C8	1.222 (3)	C5—C6	1.382 (4)
N1—C1	1.431 (3)	C8—C9	1.493 (4)
N1—C7	1.324 (3)	C2—H3	0.9300
N2—C7	1.394 (3)	C4—H4	0.9300
N2—C8	1.367 (4)	C5—H5	0.9300
N1—H1	0.8600	C6—H6	0.9300
N2—H2	0.8600	C9—H9A	0.9600
C1—C6	1.374 (3)	C9—H9B	0.9600
C1—C2	1.383 (4)	C9—H9C	0.9600
C2—C3	1.379 (4)
C1—N1—C7	124.9 (2)	N1—C7—N2	116.3 (2)
C7—N2—C8	128.42 (19)	O1—C8—C9	122.5 (3)
C1—N1—H1	118.00	N2—C8—C9	114.8 (2)
C7—N1—H1	118.00	O1—C8—N2	122.7 (2)
C7—N2—H2	116.00	C1—C2—H3	121.00
C8—N2—H2	116.00	C3—C2—H3	121.00
N1—C1—C2	120.5 (2)	C3—C4—H4	120.00
N1—C1—C6	118.1 (3)	C5—C4—H4	120.00
C2—C1—C6	121.3 (2)	C4—C5—H5	120.00
C1—C2—C3	118.1 (2)	C6—C5—H5	120.00
Cl1—C3—C4	118.6 (2)	C1—C6—H6	120.00
C2—C3—C4	121.7 (3)	C5—C6—H6	120.00
Cl1—C3—C2	119.68 (19)	C8—C9—H9A	109.00
C3—C4—C5	119.1 (3)	C8—C9—H9B	109.00
C4—C5—C6	120.7 (3)	C8—C9—H9C	109.00
C1—C6—C5	119.2 (3)	H9A—C9—H9B	109.00
S1—C7—N1	125.0 (2)	H9A—C9—H9C	109.00
S1—C7—N2	118.65 (16)	H9B—C9—H9C	109.00
C7—N1—C1—C2	63.5 (3)	C6—C1—C2—C3	0.6 (4)
C7—N1—C1—C6	−119.0 (3)	N1—C1—C6—C5	−176.9 (2)
C1—N1—C7—S1	1.1 (4)	C2—C1—C6—C5	0.6 (4)
C1—N1—C7—N2	−179.9 (2)	C1—C2—C3—Cl1	−179.9 (2)
C8—N2—C7—S1	179.9 (2)	C1—C2—C3—C4	−0.8 (4)
C8—N2—C7—N1	0.8 (4)	Cl1—C3—C4—C5	179.0 (2)
C7—N2—C8—O1	−0.3 (4)	C2—C3—C4—C5	−0.1 (4)
C7—N2—C8—C9	−179.5 (2)	C3—C4—C5—C6	1.3 (4)
N1—C1—C2—C3	178.0 (2)	C4—C5—C6—C1	−1.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	1.96	2.648 (3)	136
N2—H2···S1i	0.86	2.56	3.4095 (18)	170
C9—H9A···S1ii	0.96	2.85	3.799 (3)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.86	1.96	2.648 (3)	136
N2—H2⋯S1i	0.86	2.56	3.4095 (18)	170
C9—H9A⋯S1ii	0.96	2.85	3.799 (3)	170

Symmetry codes: (i) ; (ii) .