1-Benzoyl-3-(2,4,5-trichloro-phen-yl)thio-urea.

The benzene and phenyl rings in the title compound, C(14)H(9)Cl(3)N(2)OS, form a dihedral angle of 40.98 (6)°. The mol-ecule exists in the thione form with typical thio-urea C-S [1.666 (2) Å] and C-O [1.227 (3) Å] bond lengths as well as shortened C-N bonds [1.345 (3) and 1.386 (2) Å]. An intra-molecular N-H⋯O hydrogen bond stabilizes the mol-ecular conformation. In the crystal, pairs of N-H⋯S hydrogen bonds link the mol-ecules into centrosymmetric dimers.

Related literature

For information on thio­urea derivatives, see: Patil & Chedekel (1984 ▶); Baily et al. (1996 ▶); Namgun et al. (2001 ▶); Koch (2001 ▶); Wegner et al. (1986 ▶); Krishnamurthy et al. (1999 ▶); Murtaza et al. (2009a ▶,b ▶). For related structures, see: Khawar Rauf et al. (2009a ▶,b ▶). For bond-length data, see: Allen et al. (1987 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C14H9Cl3N2OS

M = 359.64

Monoclinic,

a = 33.111 (8) Å

b = 3.8413 (7) Å

c = 25.220 (6) Å

β = 115.995 (2)°

V = 2883.1 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.78 mm−1

T = 296 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer

Absorption correction: multi-scan (REQAB; Rigaku, 1998 ▶) T min = 0.800, T max = 1.000

11264 measured reflections

3264 independent reflections

2686 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.084

S = 1.06

3264 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.39 e Å−3

Data collection: CrystalClear (Molecular Structure Corporation and Rigaku, 2001 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶) and TEXSAN (Molecular Structure Corporation and Rigaku, 2004 ▶); software used to prepare material for publication: Yadokari-XG_2009 (Kabuto et al., 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811052780/bg2439sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811052780/bg2439Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811052780/bg2439Isup3.cml

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

C14H9Cl3N2OS	F(000) = 1456
Mr = 359.64	Dx = 1.657 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -C 2yc	Cell parameters from 3588 reflections
a = 33.111 (8) Å	θ = 3.4–27.5°
b = 3.8413 (7) Å	µ = 0.78 mm−1
c = 25.220 (6) Å	T = 296 K
β = 115.995 (2)°	Prism, colorless
V = 2883.1 (11) Å3	0.20 × 0.20 × 0.20 mm
Z = 8

Rigaku/MSC Mercury CCD diffractometer	3264 independent reflections
Radiation source: Sealed Tube	2686 reflections with I > 2σ(I)
Graphite Monochromator	Rint = 0.039
Detector resolution: 14.6306 pixels mm-1	θmax = 27.5°, θmin = 3.2°
dtprofit.ref scans	h = −42→31
Absorption correction: multi-scan (REQAB; Rigaku, 1998)	k = −3→4
Tmin = 0.800, Tmax = 1.000	l = −28→32
11264 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0345P)2 + 0.4746P] where P = (Fo2 + 2Fc2)/3
3264 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

Experimental. ????

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	0.43321 (7)	0.2438 (4)	0.27137 (9)	0.0156 (4)
S1	0.435250 (18)	0.44890 (12)	0.21438 (2)	0.01721 (13)
N1	0.39554 (6)	0.1658 (4)	0.27661 (7)	0.0169 (4)
H1	0.3985	0.0785	0.3095	0.020*
N2	0.47294 (6)	0.1480 (4)	0.31893 (7)	0.0161 (4)
H2	0.4973	0.2018	0.3166	0.019*
C2	0.47806 (7)	−0.0243 (5)	0.36979 (9)	0.0183 (4)
O1	0.44567 (5)	−0.0919 (4)	0.37941 (7)	0.0262 (4)
C3	0.35153 (7)	0.2166 (5)	0.23204 (9)	0.0159 (4)
C4	0.31883 (7)	0.3736 (5)	0.24474 (9)	0.0169 (4)
C5	0.27552 (7)	0.4225 (4)	0.20171 (10)	0.0183 (5)
H5	0.2542	0.5274	0.2110	0.022*
C6	0.26409 (7)	0.3141 (5)	0.14447 (9)	0.0175 (4)
C7	0.29612 (7)	0.1512 (5)	0.13109 (9)	0.0170 (4)
C8	0.33904 (7)	0.0996 (4)	0.17480 (9)	0.0157 (4)
H8	0.3600	−0.0154	0.1658	0.019*
Cl1	0.332696 (18)	0.51597 (12)	0.31608 (2)	0.02171 (14)
Cl2	0.210441 (17)	0.39364 (12)	0.09054 (2)	0.02358 (14)
Cl3	0.283000 (19)	0.00640 (12)	0.06075 (2)	0.02230 (14)
C9	0.52450 (7)	−0.1244 (4)	0.41257 (9)	0.0160 (4)
C10	0.56177 (7)	−0.1060 (5)	0.40132 (10)	0.0202 (5)
H10	0.5589	−0.0209	0.3653	0.024*
C11	0.60327 (7)	−0.2139 (5)	0.44354 (10)	0.0262 (5)
H11	0.6282	−0.2027	0.4356	0.031*
C12	0.60807 (7)	−0.3382 (5)	0.49742 (10)	0.0236 (5)
H12	0.6361	−0.4100	0.5257	0.028*
C13	0.57106 (8)	−0.3556 (5)	0.50921 (10)	0.0278 (5)
H13	0.5741	−0.4375	0.5455	0.033*
C14	0.52959 (8)	−0.2506 (5)	0.46687 (10)	0.0250 (5)
H14	0.5047	−0.2644	0.4747	0.030*

	U11	U22	U33	U12	U13	U23
C1	0.0159 (11)	0.0153 (9)	0.0139 (11)	0.0006 (7)	0.0050 (9)	−0.0028 (7)
S1	0.0155 (3)	0.0206 (2)	0.0151 (3)	0.00181 (18)	0.0063 (2)	0.00292 (18)
N1	0.0143 (9)	0.0239 (8)	0.0117 (9)	0.0017 (6)	0.0048 (8)	0.0036 (7)
N2	0.0117 (9)	0.0228 (8)	0.0127 (9)	0.0001 (6)	0.0042 (8)	0.0017 (6)
C2	0.0181 (12)	0.0218 (10)	0.0136 (11)	0.0013 (8)	0.0058 (10)	0.0001 (8)
O1	0.0157 (9)	0.0441 (9)	0.0203 (9)	0.0027 (6)	0.0093 (8)	0.0103 (7)
C3	0.0135 (11)	0.0174 (9)	0.0143 (11)	−0.0006 (7)	0.0037 (9)	0.0029 (7)
C4	0.0176 (12)	0.0175 (9)	0.0162 (11)	−0.0011 (7)	0.0080 (10)	0.0005 (7)
C5	0.0143 (11)	0.0184 (9)	0.0237 (13)	0.0005 (7)	0.0096 (10)	0.0022 (8)
C6	0.0108 (11)	0.0175 (9)	0.0201 (12)	−0.0010 (7)	0.0031 (9)	0.0052 (8)
C7	0.0180 (11)	0.0170 (9)	0.0142 (11)	−0.0017 (7)	0.0054 (9)	0.0007 (7)
C8	0.0143 (11)	0.0161 (9)	0.0174 (11)	0.0009 (7)	0.0076 (9)	0.0011 (8)
Cl1	0.0205 (3)	0.0287 (3)	0.0170 (3)	0.00048 (19)	0.0092 (2)	−0.00330 (19)
Cl2	0.0140 (3)	0.0281 (3)	0.0231 (3)	0.00175 (19)	0.0030 (2)	0.0041 (2)
Cl3	0.0202 (3)	0.0295 (3)	0.0133 (3)	−0.00027 (19)	0.0038 (2)	−0.00146 (19)
C9	0.0144 (11)	0.0167 (9)	0.0138 (11)	0.0013 (7)	0.0033 (9)	−0.0008 (7)
C10	0.0217 (12)	0.0211 (10)	0.0182 (12)	0.0011 (8)	0.0091 (10)	0.0033 (8)
C11	0.0178 (12)	0.0298 (11)	0.0301 (14)	0.0022 (9)	0.0097 (11)	0.0056 (9)
C12	0.0176 (12)	0.0218 (10)	0.0213 (13)	0.0016 (8)	−0.0007 (10)	0.0033 (8)
C13	0.0291 (14)	0.0337 (12)	0.0168 (13)	0.0025 (9)	0.0066 (11)	0.0055 (9)
C14	0.0193 (13)	0.0349 (11)	0.0214 (13)	0.0032 (9)	0.0093 (11)	0.0054 (9)

C1—N1	1.345 (3)	C6—Cl2	1.727 (2)
C1—N2	1.386 (2)	C7—C8	1.379 (3)
C1—S1	1.666 (2)	C7—Cl3	1.723 (2)
N1—C3	1.410 (2)	C8—H8	0.9300
N1—H1	0.8600	C9—C10	1.384 (3)
N2—C2	1.386 (3)	C9—C14	1.391 (3)
N2—H2	0.8600	C10—C11	1.382 (3)
C2—O1	1.227 (3)	C10—H10	0.9300
C2—C9	1.491 (3)	C11—C12	1.382 (3)
C3—C8	1.391 (3)	C11—H11	0.9300
C3—C4	1.394 (3)	C12—C13	1.383 (3)
C4—C5	1.380 (3)	C12—H12	0.9300
C4—Cl1	1.739 (2)	C13—C14	1.379 (3)
C5—C6	1.386 (3)	C13—H13	0.9300
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.394 (3)
N1—C1—N2	115.16 (18)	C8—C7—C6	119.9 (2)
N1—C1—S1	125.47 (16)	C8—C7—Cl3	118.89 (16)
N2—C1—S1	119.36 (15)	C6—C7—Cl3	121.24 (17)
C1—N1—C3	124.74 (18)	C7—C8—C3	121.12 (19)
C1—N1—H1	117.6	C7—C8—H8	119.4
C3—N1—H1	117.6	C3—C8—H8	119.4
C2—N2—C1	127.76 (18)	C10—C9—C14	119.02 (19)
C2—N2—H2	116.1	C10—C9—C2	124.6 (2)
C1—N2—H2	116.1	C14—C9—C2	116.36 (19)
O1—C2—N2	121.4 (2)	C11—C10—C9	120.1 (2)
O1—C2—C9	121.06 (19)	C11—C10—H10	119.9
N2—C2—C9	117.51 (18)	C9—C10—H10	119.9
C8—C3—C4	118.10 (19)	C12—C11—C10	120.5 (2)
C8—C3—N1	121.05 (18)	C12—C11—H11	119.7
C4—C3—N1	120.81 (19)	C10—C11—H11	119.7
C5—C4—C3	121.5 (2)	C11—C12—C13	119.8 (2)
C5—C4—Cl1	118.90 (16)	C11—C12—H12	120.1
C3—C4—Cl1	119.63 (16)	C13—C12—H12	120.1
C4—C5—C6	119.57 (19)	C14—C13—C12	119.6 (2)
C4—C5—H5	120.2	C14—C13—H13	120.2
C6—C5—H5	120.2	C12—C13—H13	120.2
C5—C6—C7	119.82 (19)	C13—C14—C9	120.9 (2)
C5—C6—Cl2	118.96 (16)	C13—C14—H14	119.5
C7—C6—Cl2	121.20 (17)	C9—C14—H14	119.5
N2—C1—N1—C3	−175.25 (16)	C5—C6—C7—Cl3	178.95 (14)
S1—C1—N1—C3	6.3 (3)	Cl2—C6—C7—Cl3	−2.6 (2)
N1—C1—N2—C2	1.7 (3)	C6—C7—C8—C3	−1.9 (3)
S1—C1—N2—C2	−179.68 (15)	Cl3—C7—C8—C3	178.94 (14)
C1—N2—C2—O1	−5.0 (3)	C4—C3—C8—C7	2.9 (3)
C1—N2—C2—C9	175.03 (17)	N1—C3—C8—C7	−179.55 (16)
C1—N1—C3—C8	49.5 (3)	O1—C2—C9—C10	169.75 (18)
C1—N1—C3—C4	−133.0 (2)	N2—C2—C9—C10	−10.3 (3)
C8—C3—C4—C5	−1.9 (3)	O1—C2—C9—C14	−9.0 (3)
N1—C3—C4—C5	−179.45 (17)	N2—C2—C9—C14	170.96 (17)
C8—C3—C4—Cl1	178.74 (14)	C14—C9—C10—C11	0.4 (3)
N1—C3—C4—Cl1	1.2 (2)	C2—C9—C10—C11	−178.33 (18)
C3—C4—C5—C6	−0.1 (3)	C9—C10—C11—C12	−0.5 (3)
Cl1—C4—C5—C6	179.25 (14)	C10—C11—C12—C13	0.1 (3)
C4—C5—C6—C7	1.2 (3)	C11—C12—C13—C14	0.4 (3)
C4—C5—C6—Cl2	−177.30 (14)	C12—C13—C14—C9	−0.6 (3)
C5—C6—C7—C8	−0.2 (3)	C10—C9—C14—C13	0.2 (3)
Cl2—C6—C7—C8	178.26 (14)	C2—C9—C14—C13	178.98 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	1.89	2.586 (2)	137.
N2—H2···S1i	0.86	2.83	3.6771 (19)	168.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.86	1.89	2.586 (2)	137
N2—H2⋯S1i	0.86	2.83	3.6771 (19)	168

Symmetry code: (i) .