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

The structure of the title compound, C(14)H(9)Cl(3)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 thio-carbonyl and carbonyl groups subtends dihedral angles of 48.19 (3) and 87.51 (3)° with the planes formed by the 3-chloro and 2,6-dichloro-phenyl rings, respectively; the dihedral angle between the two benzene ring planes is 45.32 (3)°. An intra-molecular N-H⋯O hydrogen bond stabilizes the mol-ecular conformation and the mol-ecules form inter-molecular N-H⋯S and N-H⋯O hydrogen bonds, generating a sheet along the a axis.

Related literature

For related structures, see: Khawar Rauf et al., (2006a ▶,b ▶; 2007 ▶). For a description of the Cambridge structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C14H9Cl3N2OS

M = 359.64

Monoclinic,

a = 10.6589 (5) Å

b = 11.2114 (5) Å

c = 13.2919 (6) Å

β = 99.942 (3)°

V = 1564.55 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.72 mm−1

T = 173 (2) K

0.47 × 0.47 × 0.45 mm

Data collection

Stoe IPDS-II two-circle diffractometer

Absorption correction: multi-scan (MULABS; Spek, 2003 ▶; Blessing, 1995 ▶) T min = 0.729, T max = 0.739

39690 measured reflections

5066 independent reflections

4674 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.094

S = 1.06

5066 reflections

199 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.65 e Å−3

Δρmin = −0.66 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: PLATON (Spek, 2003 ▶) and XP in SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: PLATON and SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808043444/pv2127sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808043444/pv2127Isup2.hkl

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

C14H9Cl3N2OS	F(000) = 728
Mr = 359.64	Dx = 1.527 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 37695 reflections
a = 10.6589 (5) Å	θ = 3.7–31.2°
b = 11.2114 (5) Å	µ = 0.72 mm−1
c = 13.2919 (6) Å	T = 173 K
β = 99.942 (3)°	Block, colourless
V = 1564.55 (12) Å3	0.47 × 0.47 × 0.45 mm
Z = 4

Stoe IPDS-II two-circle diffractometer	5066 independent reflections
Radiation source: fine-focus sealed tube	4674 reflections with I > 2σ(I)
graphite	Rint = 0.046
ω scans	θmax = 31.3°, θmin = 3.6°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −15→15
Tmin = 0.729, Tmax = 0.739	k = −16→16
39690 measured reflections	l = −19→19

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)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.094	w = 1/[σ2(Fo2) + (0.0404P)2 + 0.9365P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
5066 reflections	Δρmax = 0.65 e Å−3
199 parameters	Δρmin = −0.66 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: 0.0111 (12)

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	0.09625 (3)	0.60027 (3)	0.62517 (2)	0.02474 (9)
Cl1	0.19574 (4)	0.61905 (4)	0.23352 (3)	0.03999 (11)
Cl2	0.22323 (4)	0.18815 (4)	0.41908 (3)	0.03969 (11)
Cl3	0.33122 (7)	0.61484 (7)	0.99688 (3)	0.0735 (2)
C1	0.27158 (11)	0.45474 (11)	0.41547 (8)	0.0182 (2)
O1	0.38737 (8)	0.46303 (10)	0.43625 (7)	0.0285 (2)
N1	0.19003 (9)	0.49493 (10)	0.47738 (8)	0.01915 (19)
H1	0.1105 (19)	0.4841 (18)	0.4559 (15)	0.030 (5)*
C2	0.21866 (10)	0.55197 (10)	0.57210 (8)	0.0174 (2)
N2	0.34238 (9)	0.56439 (10)	0.61243 (8)	0.01918 (19)
H2	0.394 (2)	0.5442 (19)	0.5770 (15)	0.032 (5)*
C11	0.20320 (10)	0.39859 (11)	0.31773 (8)	0.0179 (2)
C12	0.16489 (13)	0.46736 (13)	0.23029 (10)	0.0251 (2)
C13	0.09985 (17)	0.41613 (18)	0.14040 (11)	0.0394 (4)
H13	0.0745	0.4639	0.0814	0.047*
C14	0.07264 (17)	0.29526 (19)	0.13789 (12)	0.0421 (4)
H14	0.0275	0.2606	0.0770	0.051*
C15	0.11043 (15)	0.22420 (15)	0.22299 (12)	0.0337 (3)
H15	0.0923	0.1412	0.2208	0.040*
C16	0.17558 (12)	0.27683 (12)	0.31200 (10)	0.0232 (2)
C21	0.39003 (11)	0.62132 (11)	0.70818 (9)	0.0195 (2)
C22	0.34464 (15)	0.58955 (14)	0.79662 (10)	0.0289 (3)
H22	0.2822	0.5288	0.7953	0.035*
C23	0.39279 (16)	0.64880 (16)	0.88702 (10)	0.0340 (3)
C24	0.48645 (15)	0.73570 (15)	0.89168 (11)	0.0332 (3)
H24	0.5180	0.7752	0.9541	0.040*
C25	0.53305 (14)	0.76367 (15)	0.80313 (11)	0.0318 (3)
H25	0.5984	0.8218	0.8053	0.038*
C26	0.48479 (12)	0.70721 (13)	0.71106 (10)	0.0246 (2)
H26	0.5164	0.7273	0.6507	0.030*

	U11	U22	U33	U12	U13	U23
S1	0.01676 (13)	0.03383 (17)	0.02412 (15)	−0.00159 (11)	0.00495 (10)	−0.01452 (12)
Cl1	0.0485 (2)	0.02974 (18)	0.0415 (2)	−0.00112 (15)	0.00718 (16)	0.00931 (14)
Cl2	0.0507 (2)	0.02793 (17)	0.0402 (2)	0.00109 (15)	0.00724 (16)	0.00754 (14)
Cl3	0.1095 (5)	0.0945 (5)	0.02015 (18)	−0.0585 (4)	0.0216 (2)	−0.0165 (2)
C1	0.0160 (4)	0.0228 (5)	0.0156 (4)	0.0010 (4)	0.0018 (4)	−0.0044 (4)
O1	0.0144 (4)	0.0461 (6)	0.0246 (4)	0.0004 (4)	0.0023 (3)	−0.0134 (4)
N1	0.0133 (4)	0.0275 (5)	0.0163 (4)	−0.0008 (3)	0.0016 (3)	−0.0081 (4)
C2	0.0171 (5)	0.0197 (5)	0.0152 (4)	−0.0009 (4)	0.0018 (4)	−0.0037 (4)
N2	0.0153 (4)	0.0266 (5)	0.0152 (4)	−0.0008 (4)	0.0015 (3)	−0.0061 (4)
C11	0.0160 (4)	0.0231 (5)	0.0147 (4)	−0.0007 (4)	0.0030 (4)	−0.0051 (4)
C12	0.0247 (6)	0.0317 (6)	0.0185 (5)	−0.0009 (5)	0.0023 (4)	0.0000 (4)
C13	0.0408 (8)	0.0571 (10)	0.0173 (6)	−0.0037 (7)	−0.0037 (5)	−0.0014 (6)
C14	0.0391 (8)	0.0612 (11)	0.0243 (6)	−0.0127 (8)	0.0002 (6)	−0.0189 (7)
C15	0.0315 (7)	0.0355 (7)	0.0350 (7)	−0.0098 (6)	0.0080 (5)	−0.0185 (6)
C16	0.0225 (5)	0.0246 (6)	0.0236 (5)	−0.0020 (4)	0.0070 (4)	−0.0059 (4)
C21	0.0185 (5)	0.0235 (5)	0.0151 (4)	−0.0003 (4)	−0.0005 (4)	−0.0049 (4)
C22	0.0358 (7)	0.0330 (7)	0.0168 (5)	−0.0123 (5)	0.0015 (5)	−0.0041 (5)
C23	0.0446 (8)	0.0414 (8)	0.0156 (5)	−0.0123 (7)	0.0041 (5)	−0.0064 (5)
C24	0.0341 (7)	0.0410 (8)	0.0222 (6)	−0.0079 (6)	−0.0016 (5)	−0.0123 (5)
C25	0.0265 (6)	0.0382 (8)	0.0300 (6)	−0.0108 (5)	0.0027 (5)	−0.0129 (6)
C26	0.0206 (5)	0.0305 (6)	0.0229 (5)	−0.0044 (5)	0.0038 (4)	−0.0076 (5)

S1—C2	1.6766 (12)	C13—H13	0.9500
Cl1—C12	1.7313 (15)	C14—C15	1.385 (3)
Cl2—C16	1.7386 (14)	C14—H14	0.9500
Cl3—C23	1.7433 (15)	C15—C16	1.3951 (18)
C1—O1	1.2209 (14)	C15—H15	0.9500
C1—N1	1.3721 (14)	C21—C26	1.3912 (18)
C1—C11	1.5128 (15)	C21—C22	1.3925 (18)
N1—C2	1.3980 (14)	C22—C23	1.3912 (18)
N1—H1	0.86 (2)	C22—H22	0.9500
C2—N2	1.3423 (14)	C23—C24	1.389 (2)
N2—C21	1.4360 (14)	C24—C25	1.390 (2)
N2—H2	0.82 (2)	C24—H24	0.9500
C11—C12	1.3957 (17)	C25—C26	1.3947 (17)
C11—C16	1.3957 (17)	C25—H25	0.9500
C12—C13	1.3971 (19)	C26—H26	0.9500
C13—C14	1.385 (3)
O1—C1—N1	124.03 (10)	C14—C15—C16	118.77 (14)
O1—C1—C11	122.98 (10)	C14—C15—H15	120.6
N1—C1—C11	112.99 (9)	C16—C15—H15	120.6
C1—N1—C2	128.90 (10)	C15—C16—C11	121.96 (13)
C1—N1—H1	116.6 (13)	C15—C16—Cl2	118.99 (11)
C2—N1—H1	114.5 (13)	C11—C16—Cl2	119.05 (9)
N2—C2—N1	116.98 (10)	C26—C21—C22	120.68 (11)
N2—C2—S1	125.50 (9)	C26—C21—N2	118.43 (11)
N1—C2—S1	117.52 (8)	C22—C21—N2	120.88 (11)
C2—N2—C21	124.95 (10)	C23—C22—C21	118.48 (13)
C2—N2—H2	117.2 (14)	C23—C22—H22	120.8
C21—N2—H2	117.5 (14)	C21—C22—H22	120.8
C12—C11—C16	117.79 (11)	C24—C23—C22	121.91 (13)
C12—C11—C1	120.90 (11)	C24—C23—Cl3	119.18 (10)
C16—C11—C1	121.31 (11)	C22—C23—Cl3	118.89 (12)
C11—C12—C13	121.04 (14)	C23—C24—C25	118.67 (12)
C11—C12—Cl1	119.67 (10)	C23—C24—H24	120.7
C13—C12—Cl1	119.28 (12)	C25—C24—H24	120.7
C14—C13—C12	119.59 (15)	C24—C25—C26	120.60 (13)
C14—C13—H13	120.2	C24—C25—H25	119.7
C12—C13—H13	120.2	C26—C25—H25	119.7
C13—C14—C15	120.85 (13)	C21—C26—C25	119.62 (12)
C13—C14—H14	119.6	C21—C26—H26	120.2
C15—C14—H14	119.6	C25—C26—H26	120.2
O1—C1—N1—C2	0.6 (2)	C14—C15—C16—C11	0.2 (2)
C11—C1—N1—C2	−179.35 (12)	C14—C15—C16—Cl2	179.98 (12)
C1—N1—C2—N2	−4.11 (19)	C12—C11—C16—C15	−0.86 (18)
C1—N1—C2—S1	175.27 (11)	C1—C11—C16—C15	178.74 (12)
N1—C2—N2—C21	179.40 (11)	C12—C11—C16—Cl2	179.39 (9)
S1—C2—N2—C21	0.07 (18)	C1—C11—C16—Cl2	−1.01 (16)
O1—C1—C11—C12	−90.46 (16)	C2—N2—C21—C26	−130.55 (14)
N1—C1—C11—C12	89.48 (14)	C2—N2—C21—C22	50.86 (18)
O1—C1—C11—C16	89.95 (16)	C26—C21—C22—C23	2.4 (2)
N1—C1—C11—C16	−90.11 (14)	N2—C21—C22—C23	−179.07 (14)
C16—C11—C12—C13	0.68 (19)	C21—C22—C23—C24	−1.7 (3)
C1—C11—C12—C13	−178.93 (13)	C21—C22—C23—Cl3	176.96 (13)
C16—C11—C12—Cl1	179.53 (10)	C22—C23—C24—C25	−0.1 (3)
C1—C11—C12—Cl1	−0.07 (16)	Cl3—C23—C24—C25	−178.76 (14)
C11—C12—C13—C14	0.1 (2)	C23—C24—C25—C26	1.3 (3)
Cl1—C12—C13—C14	−178.73 (14)	C22—C21—C26—C25	−1.2 (2)
C12—C13—C14—C15	−0.8 (3)	N2—C21—C26—C25	−179.82 (13)
C13—C14—C15—C16	0.6 (2)	C24—C25—C26—C21	−0.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.82 (2)	2.07 (2)	2.7190 (13)	136.0 (18)
N2—H2···O1i	0.82 (2)	2.37 (2)	3.0749 (14)	145.5 (18)
N1—H1···S1ii	0.86 (2)	2.47 (2)	3.2974 (10)	163.6 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.82 (2)	2.07 (2)	2.7190 (13)	136.0 (18)
N2—H2⋯O1i	0.82 (2)	2.37 (2)	3.0749 (14)	145.5 (18)
N1—H1⋯S1ii	0.86 (2)	2.47 (2)	3.2974 (10)	163.6 (18)

Symmetry codes: (i) ; (ii) .