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

In the title compound, C(9)H(8)Cl(2)N(2)OS, the conformation of one of the N-H bonds is anti to the C=S group and the other is anti to the C=O group. Further, the conformations of the amide C=S and the C=O group are anti to each other. The 2,6-dichloro-phenyl ring and the 3-acetyl-thio-urea side chain are inclined to one another at a dihedral angle of 83.44 (5)°. An intra-molecular N-H⋯O hydrogen bond occurs. In the crystal, mol-ecules form inversion dimers through pairs of N-H⋯S hydrogen bonds.

Related literature

For studies of the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Bhat & Gowda (2000 ▶); Gowda et al. (2003 ▶); 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

C9H8Cl2N2OS

M = 263.13

Triclinic,

a = 7.729 (1) Å

b = 8.047 (1) Å

c = 10.015 (1) Å

α = 88.05 (1)°

β = 76.39 (1)°

γ = 66.57 (1)°

V = 554.24 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.75 mm−1

T = 293 K

0.44 × 0.44 × 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 = 0.735, T max = 0.971

3638 measured reflections

2232 independent reflections

1930 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.095

S = 1.09

2232 reflections

143 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.37 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/S160053681202925X/sj5247sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202925X/sj5247Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681202925X/sj5247Isup3.cml

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

C9H8Cl2N2OS	Z = 2
Mr = 263.13	F(000) = 268
Triclinic, P1	Dx = 1.577 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.729 (1) Å	Cell parameters from 2085 reflections
b = 8.047 (1) Å	θ = 2.8–27.7°
c = 10.015 (1) Å	µ = 0.75 mm−1
α = 88.05 (1)°	T = 293 K
β = 76.39 (1)°	Plate, dark yellow
γ = 66.57 (1)°	0.44 × 0.44 × 0.04 mm
V = 554.24 (11) Å3

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2232 independent reflections
Radiation source: fine-focus sealed tube	1930 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.013
Rotation method data acquisition using ω and phi scans.	θmax = 26.4°, θmin = 2.8°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −9→9
Tmin = 0.735, Tmax = 0.971	k = −10→9
3638 measured reflections	l = −7→12

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) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0423P)2 + 0.2588P] where P = (Fo2 + 2Fc2)/3
2232 reflections	(Δ/σ)max = 0.005
143 parameters	Δρmax = 0.30 e Å−3
3 restraints	Δρmin = −0.37 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
C1	0.0838 (3)	0.5813 (3)	0.14414 (19)	0.0322 (4)
C2	0.2043 (3)	0.5857 (3)	0.0189 (2)	0.0359 (5)
C3	0.3407 (3)	0.4272 (3)	−0.0553 (2)	0.0447 (6)
H3	0.4218	0.4319	−0.1389	0.054*
C4	0.3548 (3)	0.2629 (3)	−0.0042 (3)	0.0488 (6)
H4	0.4466	0.1563	−0.0537	0.059*
C5	0.2355 (4)	0.2534 (3)	0.1192 (3)	0.0465 (6)
H5	0.2449	0.1416	0.1525	0.056*
C6	0.1012 (3)	0.4131 (3)	0.1927 (2)	0.0374 (5)
C7	−0.0252 (3)	0.8408 (3)	0.30587 (19)	0.0300 (4)
C8	−0.3676 (3)	1.0659 (3)	0.3506 (2)	0.0356 (5)
C9	−0.4980 (3)	1.2494 (3)	0.4221 (3)	0.0524 (6)
H9A	−0.4576	1.3397	0.3769	0.079*
H9B	−0.4901	1.2490	0.5164	0.079*
H9C	−0.6296	1.2768	0.4187	0.079*
N1	−0.0603 (2)	0.7439 (2)	0.21891 (17)	0.0342 (4)
H1N	−0.175 (3)	0.782 (3)	0.210 (2)	0.041*
N2	−0.1818 (2)	0.9960 (2)	0.36945 (17)	0.0349 (4)
H2N	−0.156 (3)	1.053 (3)	0.426 (2)	0.042*
O1	−0.4216 (2)	0.9862 (2)	0.28007 (18)	0.0530 (5)
Cl1	0.18527 (10)	0.79226 (8)	−0.04530 (6)	0.05449 (19)
Cl2	−0.04629 (11)	0.40151 (9)	0.34891 (6)	0.0607 (2)
S1	0.19132 (8)	0.78798 (8)	0.33840 (6)	0.04599 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0283 (9)	0.0309 (10)	0.0335 (10)	−0.0061 (8)	−0.0087 (8)	−0.0104 (8)
C2	0.0328 (10)	0.0362 (11)	0.0355 (10)	−0.0091 (9)	−0.0099 (8)	−0.0045 (8)
C3	0.0327 (11)	0.0510 (14)	0.0374 (11)	−0.0048 (10)	−0.0038 (9)	−0.0144 (10)
C4	0.0393 (12)	0.0385 (13)	0.0534 (14)	0.0040 (10)	−0.0152 (11)	−0.0198 (11)
C5	0.0501 (13)	0.0290 (11)	0.0562 (14)	−0.0061 (10)	−0.0214 (11)	−0.0052 (10)
C6	0.0375 (11)	0.0367 (11)	0.0378 (11)	−0.0129 (9)	−0.0110 (9)	−0.0062 (9)
C7	0.0291 (8)	0.0289 (10)	0.0276 (9)	−0.0089 (8)	−0.0025 (7)	−0.0048 (8)
C8	0.0324 (10)	0.0336 (11)	0.0340 (10)	−0.0077 (9)	−0.0045 (8)	−0.0046 (8)
C9	0.0411 (13)	0.0410 (13)	0.0574 (15)	0.0012 (10)	−0.0084 (11)	−0.0153 (11)
N1	0.0258 (8)	0.0321 (9)	0.0393 (9)	−0.0054 (7)	−0.0070 (7)	−0.0125 (7)
N2	0.0315 (9)	0.0324 (9)	0.0353 (9)	−0.0067 (7)	−0.0066 (7)	−0.0131 (7)
O1	0.0351 (8)	0.0514 (10)	0.0654 (11)	−0.0058 (7)	−0.0162 (8)	−0.0201 (8)
Cl1	0.0596 (4)	0.0476 (4)	0.0521 (4)	−0.0206 (3)	−0.0080 (3)	0.0075 (3)
Cl2	0.0744 (5)	0.0573 (4)	0.0485 (4)	−0.0325 (3)	−0.0004 (3)	0.0009 (3)
S1	0.0299 (3)	0.0539 (4)	0.0455 (3)	−0.0060 (2)	−0.0090 (2)	−0.0226 (3)

C1—C2	1.384 (3)	C7—N1	1.329 (2)
C1—C6	1.388 (3)	C7—N2	1.385 (2)
C1—N1	1.424 (2)	C7—S1	1.664 (2)
C2—C3	1.384 (3)	C8—O1	1.211 (2)
C2—Cl1	1.725 (2)	C8—N2	1.376 (3)
C3—C4	1.374 (4)	C8—C9	1.503 (3)
C3—H3	0.9300	C9—H9A	0.9600
C4—C5	1.377 (4)	C9—H9B	0.9600
C4—H4	0.9300	C9—H9C	0.9600
C5—C6	1.384 (3)	N1—H1N	0.836 (16)
C5—H5	0.9300	N2—H2N	0.845 (16)
C6—Cl2	1.730 (2)
C2—C1—C6	118.15 (18)	N1—C7—N2	115.94 (17)
C2—C1—N1	121.29 (19)	N1—C7—S1	124.10 (15)
C6—C1—N1	120.50 (18)	N2—C7—S1	119.95 (14)
C1—C2—C3	121.2 (2)	O1—C8—N2	122.41 (18)
C1—C2—Cl1	119.41 (15)	O1—C8—C9	122.4 (2)
C3—C2—Cl1	119.43 (18)	N2—C8—C9	115.21 (18)
C4—C3—C2	119.3 (2)	C8—C9—H9A	109.5
C4—C3—H3	120.4	C8—C9—H9B	109.5
C2—C3—H3	120.4	H9A—C9—H9B	109.5
C3—C4—C5	121.1 (2)	C8—C9—H9C	109.5
C3—C4—H4	119.4	H9A—C9—H9C	109.5
C5—C4—H4	119.4	H9B—C9—H9C	109.5
C4—C5—C6	118.8 (2)	C7—N1—C1	123.48 (17)
C4—C5—H5	120.6	C7—N1—H1N	116.3 (16)
C6—C5—H5	120.6	C1—N1—H1N	120.3 (16)
C5—C6—C1	121.4 (2)	C8—N2—C7	128.23 (17)
C5—C6—Cl2	118.92 (18)	C8—N2—H2N	117.7 (16)
C1—C6—Cl2	119.64 (15)	C7—N2—H2N	114.0 (16)
C6—C1—C2—C3	−1.0 (3)	N1—C1—C6—C5	177.63 (19)
N1—C1—C2—C3	−178.23 (18)	C2—C1—C6—Cl2	179.87 (15)
C6—C1—C2—Cl1	179.45 (15)	N1—C1—C6—Cl2	−2.8 (3)
N1—C1—C2—Cl1	2.2 (3)	N2—C7—N1—C1	179.64 (19)
C1—C2—C3—C4	0.7 (3)	S1—C7—N1—C1	0.7 (3)
Cl1—C2—C3—C4	−179.70 (17)	C2—C1—N1—C7	−86.2 (3)
C2—C3—C4—C5	0.2 (3)	C6—C1—N1—C7	96.6 (2)
C3—C4—C5—C6	−0.8 (3)	O1—C8—N2—C7	6.5 (4)
C4—C5—C6—C1	0.5 (3)	C9—C8—N2—C7	−172.7 (2)
C4—C5—C6—Cl2	−179.01 (17)	N1—C7—N2—C8	−2.4 (3)
C2—C1—C6—C5	0.3 (3)	S1—C7—N2—C8	176.56 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.84 (2)	1.94 (2)	2.631 (2)	139 (2)
N2—H2N···S1i	0.85 (2)	2.63 (2)	3.4252 (17)	158 (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)	1.94 (2)	2.631 (2)	139 (2)
N2—H2N⋯S1i	0.85 (2)	2.63 (2)	3.4252 (17)	158 (2)

Symmetry code: (i) .