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

In the crystal structure of the title compound, C(9)H(8)Cl(2)N(2)OS, there are two mol-ecules in the asymmetric unit which are connected by a pair of N-H⋯S hydrogen bonds. An intra-molecular N-H⋯O hydrogen bond stabilizes the mol-ecular conformation of each molecule.

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 ▶). For N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007 ▶). For N-chloro­aryl­sulfonamides, see: Gowda & Ramachandra (1989 ▶), Shetty & Gowda (2004 ▶).

Experimental

Crystal data

C9H8Cl2N2OS

M = 263.13

Triclinic,

a = 7.8475 (6) Å

b = 9.5987 (7) Å

c = 15.141 (1) Å

α = 90.044 (6)°

β = 91.099 (6)°

γ = 100.208 (6)°

V = 1122.24 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.74 mm−1

T = 293 K

0.46 × 0.44 × 0.36 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.728, T max = 0.777

7971 measured reflections

4578 independent reflections

3885 reflections with I > 2σ(I)

R int = 0.011

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.106

S = 1.04

4578 reflections

285 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.67 e Å−3

Δρmin = −0.72 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; 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/S1600536812030176/bt5964sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030176/bt5964Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812030176/bt5964Isup3.cml

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

C9H8Cl2N2OS	Z = 4
Mr = 263.13	F(000) = 536
Triclinic, P1	Dx = 1.557 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8475 (6) Å	Cell parameters from 4895 reflections
b = 9.5987 (7) Å	θ = 2.5–27.7°
c = 15.141 (1) Å	µ = 0.74 mm−1
α = 90.044 (6)°	T = 293 K
β = 91.099 (6)°	Prism, light yellow
γ = 100.208 (6)°	0.46 × 0.44 × 0.36 mm
V = 1122.24 (14) Å3

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	4578 independent reflections
Radiation source: fine-focus sealed tube	3885 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.011
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 2.5°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −9→8
Tmin = 0.728, Tmax = 0.777	k = −11→10
7971 measured reflections	l = −18→17

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) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0403P)2 + 0.8845P] where P = (Fo2 + 2Fc2)/3
4578 reflections	(Δ/σ)max = 0.002
285 parameters	Δρmax = 0.67 e Å−3
4 restraints	Δρmin = −0.72 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
Cl1	0.39378 (10)	0.64301 (8)	−0.04620 (5)	0.0675 (2)
Cl2	0.51017 (13)	0.81095 (13)	−0.21801 (5)	0.0956 (3)
S1	0.86892 (8)	0.69266 (7)	0.15722 (5)	0.05361 (18)
O1	0.3014 (2)	0.6735 (2)	0.21951 (13)	0.0687 (6)
N1	0.5647 (3)	0.7665 (2)	0.11819 (13)	0.0457 (5)
H1N	0.458 (2)	0.754 (3)	0.1305 (18)	0.055*
N2	0.5747 (2)	0.6306 (2)	0.24233 (12)	0.0397 (4)
H2N	0.639 (3)	0.591 (3)	0.2760 (15)	0.048*
C1	0.6232 (3)	0.8420 (2)	0.04055 (15)	0.0412 (5)
C2	0.5487 (3)	0.7949 (3)	−0.04025 (16)	0.0441 (5)
C3	0.5999 (3)	0.8705 (3)	−0.11636 (17)	0.0526 (6)
C4	0.7246 (3)	0.9910 (3)	−0.11191 (19)	0.0561 (7)
H4	0.7589	1.0412	−0.1630	0.067*
C5	0.7983 (3)	1.0369 (3)	−0.0314 (2)	0.0564 (7)
H5	0.8827	1.1182	−0.0283	0.068*
C6	0.7479 (3)	0.9632 (3)	0.04515 (18)	0.0512 (6)
H6	0.7977	0.9951	0.0993	0.061*
C7	0.6603 (3)	0.6990 (2)	0.17092 (14)	0.0374 (5)
C8	0.4039 (3)	0.6220 (3)	0.26475 (16)	0.0451 (5)
C9	0.3545 (3)	0.5463 (3)	0.34875 (18)	0.0607 (7)
H9A	0.2336	0.5439	0.3587	0.073*
H9B	0.4214	0.5949	0.3969	0.073*
H9C	0.3768	0.4513	0.3449	0.073*
Cl3	0.68592 (11)	−0.06753 (7)	0.35412 (5)	0.0693 (2)
Cl4	0.60530 (13)	−0.20874 (9)	0.53971 (7)	0.0884 (3)
S2	0.78757 (8)	0.45828 (6)	0.39216 (4)	0.04733 (16)
O2	1.0172 (3)	0.1780 (2)	0.20337 (14)	0.0772 (6)
N3	0.9002 (3)	0.2163 (2)	0.36075 (13)	0.0453 (5)
H3N	0.932 (3)	0.169 (3)	0.3223 (15)	0.054*
N4	0.9362 (3)	0.3818 (2)	0.24969 (13)	0.0432 (4)
H4N	0.924 (3)	0.463 (2)	0.2336 (17)	0.052*
C10	0.8602 (3)	0.1564 (2)	0.44498 (15)	0.0405 (5)
C11	0.7626 (3)	0.0208 (2)	0.44964 (16)	0.0440 (5)
C12	0.7286 (3)	−0.0417 (3)	0.53190 (18)	0.0531 (6)
C13	0.7920 (4)	0.0296 (3)	0.60792 (18)	0.0591 (7)
H13	0.7690	−0.0126	0.6627	0.071*
C14	0.8890 (4)	0.1627 (3)	0.60259 (17)	0.0570 (7)
H14	0.9317	0.2107	0.6540	0.068*
C15	0.9241 (3)	0.2264 (3)	0.52160 (16)	0.0494 (6)
H15	0.9908	0.3166	0.5187	0.059*
C16	0.8777 (3)	0.3440 (2)	0.33372 (14)	0.0378 (5)
C17	1.0071 (3)	0.3013 (3)	0.18971 (17)	0.0509 (6)
C18	1.0707 (4)	0.3771 (3)	0.10721 (18)	0.0633 (7)
H18A	1.0801	0.3093	0.0618	0.076*
H18B	1.1822	0.4344	0.1187	0.076*
H18C	0.9906	0.4364	0.0882	0.076*

	U11	U22	U33	U12	U13	U23
Cl1	0.0655 (4)	0.0654 (4)	0.0644 (4)	−0.0075 (3)	−0.0080 (3)	0.0111 (3)
Cl2	0.0922 (6)	0.1402 (9)	0.0462 (4)	−0.0007 (6)	−0.0098 (4)	0.0234 (5)
S1	0.0414 (3)	0.0606 (4)	0.0619 (4)	0.0158 (3)	0.0148 (3)	0.0243 (3)
O1	0.0413 (10)	0.1009 (16)	0.0665 (12)	0.0190 (10)	0.0075 (9)	0.0325 (11)
N1	0.0369 (10)	0.0585 (12)	0.0425 (11)	0.0101 (9)	0.0053 (8)	0.0153 (9)
N2	0.0370 (10)	0.0457 (10)	0.0369 (10)	0.0085 (8)	0.0031 (8)	0.0084 (8)
C1	0.0373 (11)	0.0450 (12)	0.0440 (12)	0.0140 (9)	0.0063 (9)	0.0114 (10)
C2	0.0390 (12)	0.0481 (13)	0.0469 (13)	0.0124 (10)	0.0013 (10)	0.0109 (10)
C3	0.0494 (14)	0.0666 (16)	0.0448 (13)	0.0184 (12)	0.0053 (11)	0.0165 (12)
C4	0.0547 (15)	0.0618 (16)	0.0570 (16)	0.0228 (13)	0.0183 (12)	0.0259 (13)
C5	0.0490 (14)	0.0439 (13)	0.0766 (19)	0.0075 (11)	0.0175 (13)	0.0136 (12)
C6	0.0496 (14)	0.0492 (14)	0.0549 (15)	0.0084 (11)	0.0046 (11)	0.0040 (11)
C7	0.0406 (11)	0.0359 (11)	0.0352 (11)	0.0054 (9)	0.0019 (9)	−0.0002 (8)
C8	0.0404 (12)	0.0504 (13)	0.0435 (13)	0.0054 (10)	0.0047 (10)	0.0039 (10)
C9	0.0482 (14)	0.0785 (19)	0.0559 (16)	0.0111 (13)	0.0135 (12)	0.0228 (14)
Cl3	0.0901 (5)	0.0490 (4)	0.0630 (4)	−0.0018 (3)	−0.0183 (4)	−0.0066 (3)
Cl4	0.1007 (6)	0.0566 (4)	0.0989 (7)	−0.0115 (4)	0.0078 (5)	0.0281 (4)
S2	0.0601 (4)	0.0442 (3)	0.0409 (3)	0.0175 (3)	0.0060 (3)	0.0027 (2)
O2	0.1154 (18)	0.0608 (13)	0.0642 (13)	0.0367 (12)	0.0298 (12)	0.0009 (10)
N3	0.0624 (13)	0.0365 (10)	0.0384 (10)	0.0122 (9)	0.0063 (9)	−0.0002 (8)
N4	0.0492 (11)	0.0402 (10)	0.0407 (10)	0.0088 (9)	0.0072 (8)	0.0048 (8)
C10	0.0456 (12)	0.0361 (11)	0.0413 (12)	0.0115 (9)	0.0024 (9)	0.0030 (9)
C11	0.0471 (13)	0.0383 (12)	0.0470 (13)	0.0096 (10)	−0.0026 (10)	0.0009 (10)
C12	0.0540 (14)	0.0435 (13)	0.0625 (16)	0.0096 (11)	0.0084 (12)	0.0135 (11)
C13	0.0730 (18)	0.0640 (17)	0.0450 (14)	0.0233 (14)	0.0111 (13)	0.0147 (12)
C14	0.0720 (18)	0.0622 (16)	0.0406 (13)	0.0232 (14)	−0.0027 (12)	−0.0037 (11)
C15	0.0575 (15)	0.0424 (13)	0.0480 (14)	0.0082 (11)	−0.0027 (11)	−0.0019 (10)
C16	0.0360 (11)	0.0369 (11)	0.0385 (11)	0.0015 (9)	−0.0010 (9)	0.0004 (9)
C17	0.0534 (14)	0.0553 (15)	0.0454 (13)	0.0127 (12)	0.0066 (11)	−0.0024 (11)
C18	0.0667 (17)	0.078 (2)	0.0479 (15)	0.0187 (15)	0.0160 (13)	0.0028 (13)

Cl1—C2	1.726 (2)	Cl3—C11	1.719 (2)
Cl2—C3	1.734 (3)	Cl4—C12	1.725 (3)
S1—C7	1.666 (2)	S2—C16	1.669 (2)
O1—C8	1.217 (3)	O2—C17	1.218 (3)
N1—C7	1.330 (3)	N3—C16	1.332 (3)
N1—C1	1.422 (3)	N3—C10	1.417 (3)
N1—H1N	0.846 (17)	N3—H3N	0.808 (17)
N2—C8	1.378 (3)	N4—C17	1.379 (3)
N2—C7	1.387 (3)	N4—C16	1.388 (3)
N2—H2N	0.843 (16)	N4—H4N	0.836 (16)
C1—C6	1.382 (3)	C10—C15	1.381 (3)
C1—C2	1.386 (3)	C10—C11	1.391 (3)
C2—C3	1.390 (3)	C11—C12	1.392 (3)
C3—C4	1.378 (4)	C12—C13	1.377 (4)
C4—C5	1.377 (4)	C13—C14	1.370 (4)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.385 (4)	C14—C15	1.381 (4)
C5—H5	0.9300	C14—H14	0.9300
C6—H6	0.9300	C15—H15	0.9300
C8—C9	1.489 (3)	C17—C18	1.495 (4)
C9—H9A	0.9600	C18—H18A	0.9600
C9—H9B	0.9600	C18—H18B	0.9600
C9—H9C	0.9600	C18—H18C	0.9600
C7—N1—C1	125.50 (19)	C16—N3—C10	126.43 (19)
C7—N1—H1N	114.5 (19)	C16—N3—H3N	114 (2)
C1—N1—H1N	119.6 (19)	C10—N3—H3N	120 (2)
C8—N2—C7	128.45 (19)	C17—N4—C16	128.0 (2)
C8—N2—H2N	117.7 (18)	C17—N4—H4N	116.8 (19)
C7—N2—H2N	113.8 (18)	C16—N4—H4N	115.1 (19)
C6—C1—C2	120.1 (2)	C15—C10—C11	119.8 (2)
C6—C1—N1	121.0 (2)	C15—C10—N3	121.4 (2)
C2—C1—N1	118.9 (2)	C11—C10—N3	118.8 (2)
C1—C2—C3	119.6 (2)	C10—C11—C12	119.3 (2)
C1—C2—Cl1	120.12 (18)	C10—C11—Cl3	119.74 (18)
C3—C2—Cl1	120.3 (2)	C12—C11—Cl3	120.92 (19)
C4—C3—C2	120.4 (2)	C13—C12—C11	120.4 (2)
C4—C3—Cl2	119.6 (2)	C13—C12—Cl4	119.3 (2)
C2—C3—Cl2	120.0 (2)	C11—C12—Cl4	120.3 (2)
C5—C4—C3	119.6 (2)	C14—C13—C12	119.8 (2)
C5—C4—H4	120.2	C14—C13—H13	120.1
C3—C4—H4	120.2	C12—C13—H13	120.1
C4—C5—C6	120.6 (2)	C13—C14—C15	120.7 (2)
C4—C5—H5	119.7	C13—C14—H14	119.7
C6—C5—H5	119.7	C15—C14—H14	119.7
C1—C6—C5	119.7 (3)	C10—C15—C14	120.0 (2)
C1—C6—H6	120.2	C10—C15—H15	120.0
C5—C6—H6	120.2	C14—C15—H15	120.0
N1—C7—N2	115.39 (19)	N3—C16—N4	115.5 (2)
N1—C7—S1	125.13 (17)	N3—C16—S2	125.53 (17)
N2—C7—S1	119.48 (16)	N4—C16—S2	118.93 (16)
O1—C8—N2	122.4 (2)	O2—C17—N4	122.3 (2)
O1—C8—C9	122.6 (2)	O2—C17—C18	122.8 (2)
N2—C8—C9	115.0 (2)	N4—C17—C18	114.9 (2)
C8—C9—H9A	109.5	C17—C18—H18A	109.5
C8—C9—H9B	109.5	C17—C18—H18B	109.5
H9A—C9—H9B	109.5	H18A—C18—H18B	109.5
C8—C9—H9C	109.5	C17—C18—H18C	109.5
H9A—C9—H9C	109.5	H18A—C18—H18C	109.5
H9B—C9—H9C	109.5	H18B—C18—H18C	109.5
C7—N1—C1—C6	−65.8 (3)	C16—N3—C10—C15	−53.7 (3)
C7—N1—C1—C2	116.5 (3)	C16—N3—C10—C11	130.0 (2)
C6—C1—C2—C3	−0.1 (3)	C15—C10—C11—C12	0.9 (3)
N1—C1—C2—C3	177.6 (2)	N3—C10—C11—C12	177.3 (2)
C6—C1—C2—Cl1	179.65 (18)	C15—C10—C11—Cl3	−178.97 (19)
N1—C1—C2—Cl1	−2.6 (3)	N3—C10—C11—Cl3	−2.6 (3)
C1—C2—C3—C4	0.4 (4)	C10—C11—C12—C13	−0.4 (4)
Cl1—C2—C3—C4	−179.44 (19)	Cl3—C11—C12—C13	179.4 (2)
C1—C2—C3—Cl2	178.94 (18)	C10—C11—C12—Cl4	179.07 (18)
Cl1—C2—C3—Cl2	−0.9 (3)	Cl3—C11—C12—Cl4	−1.1 (3)
C2—C3—C4—C5	−0.2 (4)	C11—C12—C13—C14	0.0 (4)
Cl2—C3—C4—C5	−178.8 (2)	Cl4—C12—C13—C14	−179.5 (2)
C3—C4—C5—C6	−0.2 (4)	C12—C13—C14—C15	0.0 (4)
C2—C1—C6—C5	−0.2 (4)	C11—C10—C15—C14	−0.9 (4)
N1—C1—C6—C5	−177.9 (2)	N3—C10—C15—C14	−177.2 (2)
C4—C5—C6—C1	0.4 (4)	C13—C14—C15—C10	0.5 (4)
C1—N1—C7—N2	−179.0 (2)	C10—N3—C16—N4	176.4 (2)
C1—N1—C7—S1	1.4 (4)	C10—N3—C16—S2	−3.3 (4)
C8—N2—C7—N1	1.1 (3)	C17—N4—C16—N3	3.3 (3)
C8—N2—C7—S1	−179.31 (19)	C17—N4—C16—S2	−177.0 (2)
C7—N2—C8—O1	2.5 (4)	C16—N4—C17—O2	4.5 (4)
C7—N2—C8—C9	−177.0 (2)	C16—N4—C17—C18	−175.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.85 (2)	1.91 (2)	2.625 (3)	141 (3)
N2—H2N···S2	0.84 (2)	2.56 (2)	3.393 (2)	171 (2)
N3—H3N···O2	0.81 (2)	1.93 (2)	2.619 (3)	143 (3)
N4—H4N···S1	0.84 (2)	2.59 (2)	3.418 (2)	170 (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)	1.91 (2)	2.625 (3)	141 (3)
N2—H2N⋯S2	0.84 (2)	2.56 (2)	3.393 (2)	171 (2)
N3—H3N⋯O2	0.81 (2)	1.93 (2)	2.619 (3)	143 (3)
N4—H4N⋯S1	0.84 (2)	2.59 (2)	3.418 (2)	170 (2)