1-(2,6-Dichloro-benzo-yl)-3-(3,5-dichloro-phen-yl)thio-urea.

The crystal structure of the title compound, C(14)H(8)Cl(4)N(2)OS, is composed of discrete mol-ecules with bond lengths and angles quite typical for thio-urea compounds of this class. The plane containing the central SONNCC atom set subtends a dihedral angle of 31.47 (3)° with the benzene ring. An intra-molecular N-H⋯O hydrogen bond stabilizes the mol-ecular conformation and the mol-ecules form centrosymmetric dimers via inter-molecular N-H⋯S hydrogen bonds.

Related literature

For general background, see: Upadlgaya & Srivastava (1982 ▶); Wegner et al. (1986 ▶); Krishnamurthy et al. (1999 ▶). For related structures, see: Khawar Rauf et al. (2006a ▶, 2007 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For bond lengths and angles in N,N′-disubstituted thio­urea compounds, see: Arslan et al. (2004 ▶); Khawar Rauf et al. (2006b ▶); Yamin & Yusof, (2003 ▶).

Experimental

Crystal data

C14H8Cl4N2OS

M = 394.08

Monoclinic,

a = 14.7737 (13) Å

b = 10.3744 (6) Å

c = 10.6935 (11) Å

β = 97.250 (7)°

V = 1625.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.86 mm−1

T = 173 (2) K

0.42 × 0.38 × 0.21 mm

Data collection

Stoe IPDSII two-circle diffractometer

Absorption correction: multi-scan (MULABS; Spek, 2003 ▶; Blessing, 1995 ▶) T min = 0.715, T max = 0.841

12823 measured reflections

3724 independent reflections

3306 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.087

S = 1.05

3724 reflections

208 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.36 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808042736/fl2225sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042736/fl2225Isup2.hkl

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

C14H8Cl4N2OS	F(000) = 792
Mr = 394.08	Dx = 1.610 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 13230 reflections
a = 14.7737 (13) Å	θ = 3.8–27.8°
b = 10.3744 (6) Å	µ = 0.86 mm−1
c = 10.6935 (11) Å	T = 173 K
β = 97.250 (7)°	Plate, colourless
V = 1625.9 (2) Å3	0.42 × 0.38 × 0.21 mm
Z = 4

Stoe IPDSII two-circle diffractometer	3724 independent reflections
Radiation source: fine-focus sealed tube	3306 reflections with I > 2σ(I)
graphite	Rint = 0.046
ω scans	θmax = 27.5°, θmin = 3.7°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −19→19
Tmin = 0.715, Tmax = 0.841	k = −13→13
12823 measured reflections	l = −10→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.087	w = 1/[σ2(Fo2) + (0.0525P)2 + 0.486P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
3724 reflections	Δρmax = 0.44 e Å−3
208 parameters	Δρmin = −0.36 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0246 (15)

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	0.35875 (3)	0.16745 (4)	0.09234 (4)	0.02939 (13)
Cl2	0.39163 (3)	0.58457 (4)	0.39696 (4)	0.02796 (12)
Cl3	0.93189 (3)	0.14605 (4)	0.52460 (4)	0.03065 (13)
Cl4	0.97033 (3)	0.59117 (4)	0.27286 (4)	0.02639 (12)
C1	0.46669 (10)	0.35599 (15)	0.26849 (14)	0.0171 (3)
O1	0.50255 (7)	0.29825 (13)	0.36158 (11)	0.0257 (3)
N1	0.51344 (8)	0.40910 (14)	0.17722 (13)	0.0185 (3)
H1	0.4844 (15)	0.443 (2)	0.115 (2)	0.028 (5)*
S1	0.64669 (2)	0.48065 (5)	0.04928 (4)	0.02559 (13)
C2	0.60770 (10)	0.41647 (15)	0.17586 (15)	0.0168 (3)
N2	0.65773 (8)	0.36848 (14)	0.27949 (13)	0.0178 (3)
H2	0.6248 (15)	0.327 (2)	0.333 (2)	0.033 (6)*
C11	0.36443 (10)	0.37608 (15)	0.24447 (14)	0.0170 (3)
C12	0.30851 (10)	0.29239 (16)	0.16745 (15)	0.0196 (3)
C13	0.21408 (11)	0.30756 (19)	0.14814 (18)	0.0265 (4)
H13	0.1771	0.2506	0.0941	0.032*
C14	0.17491 (11)	0.40754 (19)	0.2093 (2)	0.0300 (4)
H14	0.1105	0.4177	0.1978	0.036*
C15	0.22860 (12)	0.49305 (18)	0.28705 (18)	0.0270 (4)
H15	0.2014	0.5610	0.3288	0.032*
C16	0.32308 (10)	0.47701 (16)	0.30247 (15)	0.0195 (3)
C21	0.75373 (10)	0.37152 (16)	0.31296 (14)	0.0170 (3)
C22	0.79148 (10)	0.27196 (16)	0.39134 (15)	0.0196 (3)
H22	0.7539	0.2054	0.4175	0.024*
C23	0.88510 (10)	0.27226 (16)	0.43034 (15)	0.0208 (3)
C24	0.94227 (10)	0.36829 (17)	0.39447 (15)	0.0217 (3)
H24	1.0062	0.3666	0.4205	0.026*
C25	0.90178 (10)	0.46720 (16)	0.31857 (15)	0.0189 (3)
C26	0.80870 (10)	0.47105 (16)	0.27637 (15)	0.0184 (3)
H26	0.7832	0.5394	0.2242	0.022*

	U11	U22	U33	U12	U13	U23
Cl1	0.0285 (2)	0.0291 (2)	0.0314 (2)	−0.00172 (16)	0.00678 (17)	−0.00990 (17)
Cl2	0.0319 (2)	0.0247 (2)	0.0269 (2)	−0.00439 (15)	0.00228 (17)	−0.00444 (16)
Cl3	0.0275 (2)	0.0330 (2)	0.0291 (2)	0.00629 (16)	−0.00562 (16)	0.01025 (18)
Cl4	0.01753 (19)	0.0297 (2)	0.0324 (2)	−0.00597 (14)	0.00488 (15)	0.00171 (16)
C1	0.0145 (6)	0.0204 (8)	0.0165 (7)	−0.0021 (5)	0.0017 (5)	0.0004 (6)
O1	0.0169 (5)	0.0394 (7)	0.0207 (6)	−0.0008 (5)	0.0015 (4)	0.0116 (5)
N1	0.0121 (6)	0.0269 (7)	0.0160 (6)	0.0004 (5)	0.0005 (5)	0.0066 (5)
S1	0.01402 (18)	0.0436 (3)	0.0194 (2)	0.00106 (16)	0.00325 (14)	0.01158 (17)
C2	0.0135 (6)	0.0201 (8)	0.0168 (7)	0.0008 (5)	0.0018 (5)	0.0010 (6)
N2	0.0120 (6)	0.0237 (7)	0.0177 (6)	−0.0012 (5)	0.0014 (5)	0.0037 (5)
C11	0.0138 (6)	0.0216 (8)	0.0158 (7)	−0.0009 (5)	0.0032 (5)	0.0048 (6)
C12	0.0172 (7)	0.0226 (8)	0.0192 (8)	−0.0013 (6)	0.0035 (5)	0.0014 (6)
C13	0.0169 (7)	0.0316 (9)	0.0298 (9)	−0.0065 (6)	−0.0021 (6)	0.0016 (7)
C14	0.0135 (7)	0.0371 (10)	0.0391 (10)	0.0025 (7)	0.0016 (7)	0.0051 (8)
C15	0.0222 (8)	0.0267 (9)	0.0330 (10)	0.0065 (6)	0.0065 (7)	0.0029 (7)
C16	0.0191 (7)	0.0205 (8)	0.0186 (7)	−0.0009 (6)	0.0015 (6)	0.0028 (6)
C21	0.0126 (6)	0.0226 (8)	0.0157 (7)	0.0014 (5)	0.0009 (5)	−0.0016 (6)
C22	0.0178 (7)	0.0232 (8)	0.0178 (7)	−0.0002 (6)	0.0016 (5)	0.0013 (6)
C23	0.0213 (7)	0.0244 (8)	0.0157 (7)	0.0050 (6)	−0.0010 (6)	0.0017 (6)
C24	0.0142 (6)	0.0298 (9)	0.0204 (8)	0.0020 (6)	−0.0009 (5)	−0.0026 (7)
C25	0.0150 (7)	0.0242 (8)	0.0178 (7)	−0.0024 (6)	0.0027 (5)	−0.0019 (6)
C26	0.0147 (6)	0.0213 (8)	0.0188 (7)	0.0007 (5)	0.0011 (5)	0.0005 (6)

Cl1—C12	1.7397 (17)	C13—C14	1.390 (3)
Cl2—C16	1.7417 (17)	C13—H13	0.9500
Cl3—C23	1.7414 (17)	C14—C15	1.393 (3)
Cl4—C25	1.7445 (16)	C14—H14	0.9500
C1—O1	1.224 (2)	C15—C16	1.395 (2)
C1—N1	1.3796 (19)	C15—H15	0.9500
C1—C11	1.5146 (19)	C21—C26	1.400 (2)
N1—C2	1.3967 (18)	C21—C22	1.401 (2)
N1—H1	0.82 (2)	C22—C23	1.393 (2)
S1—C2	1.6745 (16)	C22—H22	0.9500
C2—N2	1.347 (2)	C23—C24	1.391 (2)
N2—C21	1.4186 (18)	C24—C25	1.395 (2)
N2—H2	0.91 (2)	C24—H24	0.9500
C11—C12	1.394 (2)	C25—C26	1.393 (2)
C11—C16	1.396 (2)	C26—H26	0.9500
C12—C13	1.393 (2)
O1—C1—N1	124.54 (14)	C14—C15—C16	118.71 (16)
O1—C1—C11	121.70 (13)	C14—C15—H15	120.6
N1—C1—C11	113.75 (13)	C16—C15—H15	120.6
C1—N1—C2	128.18 (14)	C15—C16—C11	121.63 (15)
C1—N1—H1	118.9 (15)	C15—C16—Cl2	119.48 (13)
C2—N1—H1	112.9 (15)	C11—C16—Cl2	118.89 (12)
N2—C2—N1	114.54 (13)	C26—C21—C22	120.66 (14)
N2—C2—S1	127.07 (11)	C26—C21—N2	122.87 (14)
N1—C2—S1	118.38 (11)	C22—C21—N2	116.38 (14)
C2—N2—C21	128.79 (13)	C23—C22—C21	118.86 (15)
C2—N2—H2	114.5 (15)	C23—C22—H22	120.6
C21—N2—H2	116.7 (15)	C21—C22—H22	120.6
C12—C11—C16	118.01 (13)	C24—C23—C22	122.24 (15)
C12—C11—C1	121.24 (14)	C24—C23—Cl3	119.19 (12)
C16—C11—C1	120.72 (14)	C22—C23—Cl3	118.57 (13)
C13—C12—C11	121.66 (15)	C23—C24—C25	117.16 (14)
C13—C12—Cl1	119.56 (13)	C23—C24—H24	121.4
C11—C12—Cl1	118.78 (11)	C25—C24—H24	121.4
C14—C13—C12	118.88 (16)	C26—C25—C24	122.87 (15)
C14—C13—H13	120.6	C26—C25—Cl4	118.19 (13)
C12—C13—H13	120.6	C24—C25—Cl4	118.93 (12)
C13—C14—C15	121.08 (15)	C25—C26—C21	118.19 (14)
C13—C14—H14	119.5	C25—C26—H26	120.9
C15—C14—H14	119.5	C21—C26—H26	120.9
O1—C1—N1—C2	−4.9 (3)	C14—C15—C16—Cl2	178.83 (14)
C11—C1—N1—C2	174.63 (15)	C12—C11—C16—C15	1.5 (2)
C1—N1—C2—N2	−2.2 (2)	C1—C11—C16—C15	−176.47 (15)
C1—N1—C2—S1	177.27 (14)	C12—C11—C16—Cl2	−178.89 (12)
N1—C2—N2—C21	−173.75 (15)	C1—C11—C16—Cl2	3.2 (2)
S1—C2—N2—C21	6.9 (3)	C2—N2—C21—C26	30.3 (3)
O1—C1—C11—C12	−95.3 (2)	C2—N2—C21—C22	−152.93 (16)
N1—C1—C11—C12	85.17 (19)	C26—C21—C22—C23	−1.2 (2)
O1—C1—C11—C16	82.6 (2)	N2—C21—C22—C23	−178.08 (14)
N1—C1—C11—C16	−96.94 (18)	C21—C22—C23—C24	0.2 (2)
C16—C11—C12—C13	−0.1 (2)	C21—C22—C23—Cl3	−178.45 (12)
C1—C11—C12—C13	177.83 (15)	C22—C23—C24—C25	1.1 (2)
C16—C11—C12—Cl1	179.03 (12)	Cl3—C23—C24—C25	179.77 (12)
C1—C11—C12—Cl1	−3.0 (2)	C23—C24—C25—C26	−1.5 (2)
C11—C12—C13—C14	−1.1 (3)	C23—C24—C25—Cl4	179.11 (12)
Cl1—C12—C13—C14	179.72 (14)	C24—C25—C26—C21	0.5 (2)
C12—C13—C14—C15	1.1 (3)	Cl4—C25—C26—C21	179.94 (12)
C13—C14—C15—C16	0.2 (3)	C22—C21—C26—C25	0.9 (2)
C14—C15—C16—C11	−1.5 (3)	N2—C21—C26—C25	177.49 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.91 (2)	1.89 (2)	2.6581 (17)	141 (2)
N1—H1···S1i	0.82 (2)	2.57 (2)	3.3653 (14)	163 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.91 (2)	1.89 (2)	2.6581 (17)	141 (2)
N1—H1⋯S1i	0.82 (2)	2.57 (2)	3.3653 (14)	163 (2)

Symmetry code: (i) .