3-Chloro-N-(diphenyl-carbamothio-yl)benzamide.

In the title compound, C(20)H(15)ClN(2)OS, the bond lengths and angles in the thio-urea group are typical of thio-urea derivatives. The C-N bond lengths in the center of the mol-ecule are shorter than the normal C-N single bond due to the resonance effects in this part of the mol-ecule. The conformation of the title mol-ecule with respect to the thio-carbonyl and carbonyl groups is twisted, as reflected by the C-N-C-O and C-N-C-N torsion angles of -4.4 (6) and -53.3 (5)°, respectively. Pairs of the mol-ecules are linked into centrosymmetric dimers, stacked along the c axis via inter-molecular N-H⋯S inter-actions. There are also weak inter-molecular C-H⋯O and C-H⋯S contacts in the structure.

Related literature

For synthesis, see: Özer et al. (2009 ▶); Mansuroğlu et al. (2008 ▶); Uğur et al. (2006 ▶); Arslan et al. (2003c ▶). For general background, see: Koch (2001 ▶); Huebhr et al. (1953 ▶); Madan et al. (1991 ▶); Schroeder (1955 ▶). For related structures, see: Khawar Rauf et al. (2006 ▶, 2009 ▶); Arslan et al. (2003a ▶,b ▶); Yamin & Yusof (2003 ▶).

Experimental

Crystal data

C20H15ClN2OS

M = 366.85

Triclinic,

a = 8.196 (5) Å

b = 10.357 (6) Å

c = 11.699 (6) Å

α = 72.565 (10)°

β = 70.495 (10)°

γ = 71.303 (10)°

V = 865.8 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.35 mm−1

T = 120 (2) K

0.49 × 0.32 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.847, T max = 0.966

5401 measured reflections

3490 independent reflections

2290 reflections with I > 2σ(I)

R int = 0.080

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.146

S = 1.06

3490 reflections

230 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809001639/bq2121sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001639/bq2121Isup2.hkl

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

C20H15ClN2OS	Z = 2
Mr = 366.85	F(000) = 380
Triclinic, P1	Dx = 1.407 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.196 (5) Å	Cell parameters from 710 reflections
b = 10.357 (6) Å	θ = 3.0–26.5°
c = 11.699 (6) Å	µ = 0.35 mm−1
α = 72.565 (10)°	T = 120 K
β = 70.495 (10)°	Prism, colourless
γ = 71.303 (10)°	0.49 × 0.32 × 0.10 mm
V = 865.8 (9) Å3

Bruker SMART APEX diffractometer	3490 independent reflections
Radiation source: sealed tube	2290 reflections with I > 2σ(I)
graphite	Rint = 0.080
φ and ω scans	θmax = 26.4°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −10→10
Tmin = 0.847, Tmax = 0.966	k = −12→12
5401 measured reflections	l = −13→14

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)] = 0.061	Hydrogen site location: difference Fourier map
wR(F2) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0629P)2] where P = (Fo2 + 2Fc2)/3
3490 reflections	(Δ/σ)max < 0.001
230 parameters	Δρmax = 0.37 e Å−3
1 restraint	Δρmin = −0.31 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.51239 (14)	−0.17055 (10)	0.41549 (10)	0.0406 (3)
S1	0.36004 (12)	0.69686 (9)	0.05276 (9)	0.0269 (2)
O1	0.2248 (3)	0.3782 (2)	0.3535 (2)	0.0276 (6)
N1	0.2744 (4)	0.4535 (3)	0.1434 (3)	0.0213 (6)
H1	0.364 (3)	0.430 (3)	0.078 (2)	0.020 (9)*
N2	0.0613 (3)	0.6406 (3)	0.2112 (3)	0.0210 (6)
C1	0.2248 (4)	0.5945 (3)	0.1413 (3)	0.0210 (7)
C2	0.0059 (4)	0.7766 (4)	0.2405 (3)	0.0226 (7)
C3	−0.0764 (5)	0.8908 (4)	0.1661 (4)	0.0330 (9)
H3A	−0.0918	0.8827	0.0917	0.040*
C4	−0.1364 (5)	1.0175 (4)	0.2006 (5)	0.0464 (11)
H4A	−0.1930	1.0975	0.1494	0.056*
C5	−0.1154 (6)	1.0291 (5)	0.3079 (5)	0.0506 (12)
H5A	−0.1565	1.1169	0.3309	0.061*
C6	−0.0344 (6)	0.9132 (5)	0.3825 (4)	0.0442 (11)
H6A	−0.0227	0.9205	0.4582	0.053*
C7	0.0294 (5)	0.7869 (4)	0.3478 (3)	0.0322 (9)
H7A	0.0893	0.7075	0.3977	0.039*
C8	−0.0738 (4)	0.5643 (3)	0.2509 (3)	0.0205 (7)
C9	−0.1246 (5)	0.5352 (4)	0.1618 (3)	0.0288 (8)
H9A	−0.0697	0.5650	0.0763	0.035*
C10	−0.2535 (5)	0.4636 (4)	0.1963 (4)	0.0361 (9)
H10A	−0.2869	0.4425	0.1349	0.043*
C11	−0.3350 (5)	0.4219 (4)	0.3204 (4)	0.0337 (9)
H11A	−0.4245	0.3720	0.3447	0.040*
C12	−0.2857 (5)	0.4530 (4)	0.4097 (3)	0.0291 (8)
H12A	−0.3416	0.4243	0.4952	0.035*
C13	−0.1559 (4)	0.5254 (4)	0.3744 (3)	0.0249 (8)
H13A	−0.1235	0.5483	0.4353	0.030*
C14	0.2666 (4)	0.3508 (4)	0.2519 (3)	0.0220 (7)
C15	0.3130 (4)	0.2074 (3)	0.2337 (3)	0.0213 (7)
C16	0.3799 (4)	0.0992 (3)	0.3218 (3)	0.0235 (8)
H16A	0.3953	0.1180	0.3917	0.028*
C17	0.4235 (5)	−0.0348 (4)	0.3077 (3)	0.0279 (8)
C18	0.3970 (5)	−0.0663 (4)	0.2097 (3)	0.0299 (9)
H18A	0.4264	−0.1604	0.2021	0.036*
C19	0.3273 (5)	0.0413 (4)	0.1234 (3)	0.0314 (9)
H19A	0.3074	0.0213	0.0557	0.038*
C20	0.2864 (5)	0.1766 (4)	0.1339 (3)	0.0266 (8)
H20A	0.2397	0.2501	0.0731	0.032*

	U11	U22	U33	U12	U13	U23
Cl1	0.0544 (6)	0.0299 (5)	0.0360 (6)	−0.0082 (5)	−0.0165 (5)	−0.0022 (4)
S1	0.0276 (5)	0.0304 (5)	0.0239 (5)	−0.0124 (4)	0.0013 (4)	−0.0112 (4)
O1	0.0352 (14)	0.0317 (14)	0.0189 (13)	−0.0047 (11)	−0.0097 (11)	−0.0103 (11)
N1	0.0228 (15)	0.0256 (15)	0.0138 (15)	−0.0063 (12)	0.0024 (12)	−0.0093 (12)
N2	0.0231 (15)	0.0244 (15)	0.0165 (15)	−0.0072 (12)	−0.0029 (12)	−0.0068 (12)
C1	0.0242 (17)	0.0299 (19)	0.0124 (17)	−0.0077 (15)	−0.0065 (14)	−0.0065 (14)
C2	0.0220 (17)	0.0281 (19)	0.0188 (18)	−0.0098 (15)	−0.0006 (14)	−0.0079 (15)
C3	0.033 (2)	0.034 (2)	0.028 (2)	−0.0098 (18)	−0.0074 (17)	−0.0003 (17)
C4	0.031 (2)	0.029 (2)	0.064 (3)	−0.0037 (18)	−0.003 (2)	−0.002 (2)
C5	0.050 (3)	0.039 (3)	0.060 (3)	−0.019 (2)	0.014 (2)	−0.029 (2)
C6	0.051 (3)	0.054 (3)	0.039 (3)	−0.027 (2)	0.004 (2)	−0.028 (2)
C7	0.039 (2)	0.037 (2)	0.025 (2)	−0.0152 (18)	−0.0062 (17)	−0.0088 (17)
C8	0.0216 (17)	0.0235 (17)	0.0169 (18)	−0.0060 (14)	−0.0047 (14)	−0.0048 (14)
C9	0.0303 (19)	0.043 (2)	0.0161 (18)	−0.0148 (18)	−0.0026 (15)	−0.0084 (16)
C10	0.042 (2)	0.045 (2)	0.031 (2)	−0.0138 (19)	−0.0168 (19)	−0.0099 (19)
C11	0.028 (2)	0.040 (2)	0.038 (2)	−0.0171 (18)	−0.0115 (18)	−0.0034 (18)
C12	0.0247 (19)	0.036 (2)	0.022 (2)	−0.0082 (17)	−0.0016 (16)	−0.0041 (16)
C13	0.0244 (18)	0.0297 (19)	0.0222 (19)	−0.0059 (15)	−0.0062 (15)	−0.0086 (15)
C14	0.0164 (16)	0.0313 (19)	0.0201 (19)	−0.0070 (14)	−0.0038 (14)	−0.0077 (15)
C15	0.0192 (16)	0.0293 (19)	0.0173 (18)	−0.0104 (14)	0.0000 (14)	−0.0082 (15)
C16	0.0228 (17)	0.032 (2)	0.0175 (18)	−0.0119 (15)	−0.0003 (14)	−0.0081 (15)
C17	0.0269 (18)	0.031 (2)	0.023 (2)	−0.0121 (17)	−0.0033 (15)	−0.0002 (16)
C18	0.034 (2)	0.026 (2)	0.035 (2)	−0.0126 (16)	−0.0063 (17)	−0.0135 (17)
C19	0.037 (2)	0.038 (2)	0.028 (2)	−0.0163 (18)	−0.0071 (18)	−0.0129 (18)
C20	0.0290 (19)	0.032 (2)	0.0213 (19)	−0.0114 (16)	−0.0076 (16)	−0.0045 (16)

Cl1—C17	1.730 (4)	C8—C9	1.382 (4)
S1—C1	1.659 (3)	C9—C10	1.366 (5)
O1—C14	1.216 (4)	C9—H9A	0.9500
N1—C1	1.380 (4)	C10—C11	1.379 (5)
N1—C14	1.388 (4)	C10—H10A	0.9500
N1—H1	0.894 (10)	C11—C12	1.387 (5)
N2—C1	1.336 (4)	C11—H11A	0.9500
N2—C8	1.437 (4)	C12—C13	1.378 (5)
N2—C2	1.442 (4)	C12—H12A	0.9500
C2—C3	1.369 (5)	C13—H13A	0.9500
C2—C7	1.372 (5)	C14—C15	1.473 (5)
C3—C4	1.378 (5)	C15—C16	1.382 (5)
C3—H3A	0.9500	C15—C20	1.395 (4)
C4—C5	1.367 (6)	C16—C17	1.364 (5)
C4—H4A	0.9500	C16—H16A	0.9500
C5—C6	1.375 (6)	C17—C18	1.380 (5)
C5—H5A	0.9500	C18—C19	1.375 (5)
C6—C7	1.374 (5)	C18—H18A	0.9500
C6—H6A	0.9500	C19—C20	1.367 (5)
C7—H7A	0.9500	C19—H19A	0.9500
C8—C13	1.370 (5)	C20—H20A	0.9500
C1—N1—C14	123.6 (3)	C9—C10—C11	119.9 (3)
C1—N1—H1	114 (2)	C9—C10—H10A	120.0
C14—N1—H1	115 (2)	C11—C10—H10A	120.0
C1—N2—C8	122.0 (3)	C10—C11—C12	119.8 (3)
C1—N2—C2	121.4 (3)	C10—C11—H11A	120.1
C8—N2—C2	116.3 (3)	C12—C11—H11A	120.1
N2—C1—N1	115.3 (3)	C13—C12—C11	120.1 (3)
N2—C1—S1	123.8 (3)	C13—C12—H12A	120.0
N1—C1—S1	120.9 (3)	C11—C12—H12A	120.0
C3—C2—C7	121.0 (3)	C8—C13—C12	119.7 (3)
C3—C2—N2	120.6 (3)	C8—C13—H13A	120.2
C7—C2—N2	118.3 (3)	C12—C13—H13A	120.2
C2—C3—C4	119.0 (4)	O1—C14—N1	122.1 (3)
C2—C3—H3A	120.5	O1—C14—C15	123.2 (3)
C4—C3—H3A	120.5	N1—C14—C15	114.7 (3)
C5—C4—C3	120.6 (4)	C16—C15—C20	119.1 (3)
C5—C4—H4A	119.7	C16—C15—C14	118.1 (3)
C3—C4—H4A	119.7	C20—C15—C14	122.7 (3)
C4—C5—C6	119.8 (4)	C17—C16—C15	119.5 (3)
C4—C5—H5A	120.1	C17—C16—H16A	120.3
C6—C5—H5A	120.1	C15—C16—H16A	120.3
C7—C6—C5	120.2 (4)	C16—C17—C18	121.8 (3)
C7—C6—H6A	119.9	C16—C17—Cl1	119.8 (3)
C5—C6—H6A	119.9	C18—C17—Cl1	118.4 (3)
C2—C7—C6	119.3 (4)	C19—C18—C17	118.6 (3)
C2—C7—H7A	120.3	C19—C18—H18A	120.7
C6—C7—H7A	120.3	C17—C18—H18A	120.7
C13—C8—C9	120.3 (3)	C20—C19—C18	120.7 (3)
C13—C8—N2	120.9 (3)	C20—C19—H19A	119.7
C9—C8—N2	118.7 (3)	C18—C19—H19A	119.7
C10—C9—C8	120.2 (3)	C19—C20—C15	120.3 (3)
C10—C9—H9A	119.9	C19—C20—H20A	119.9
C8—C9—H9A	119.9	C15—C20—H20A	119.9
C8—N2—C1—N1	−20.3 (4)	N2—C8—C9—C10	−179.6 (3)
C2—N2—C1—N1	166.0 (3)	C8—C9—C10—C11	0.9 (6)
C8—N2—C1—S1	157.6 (2)	C9—C10—C11—C12	0.1 (6)
C2—N2—C1—S1	−16.2 (4)	C10—C11—C12—C13	0.0 (6)
C14—N1—C1—N2	−53.3 (4)	C9—C8—C13—C12	2.1 (5)
C14—N1—C1—S1	128.9 (3)	N2—C8—C13—C12	179.6 (3)
C1—N2—C2—C3	91.3 (4)	C11—C12—C13—C8	−1.1 (5)
C8—N2—C2—C3	−82.8 (4)	C1—N1—C14—O1	−4.4 (5)
C1—N2—C2—C7	−92.0 (4)	C1—N1—C14—C15	175.7 (3)
C8—N2—C2—C7	93.9 (4)	O1—C14—C15—C16	−26.1 (5)
C7—C2—C3—C4	−0.2 (5)	N1—C14—C15—C16	153.8 (3)
N2—C2—C3—C4	176.4 (3)	O1—C14—C15—C20	151.6 (3)
C2—C3—C4—C5	−0.4 (6)	N1—C14—C15—C20	−28.4 (4)
C3—C4—C5—C6	−0.4 (6)	C20—C15—C16—C17	2.0 (5)
C4—C5—C6—C7	1.8 (6)	C14—C15—C16—C17	179.8 (3)
C3—C2—C7—C6	1.5 (5)	C15—C16—C17—C18	−2.3 (5)
N2—C2—C7—C6	−175.1 (3)	C15—C16—C17—Cl1	178.4 (2)
C5—C6—C7—C2	−2.3 (6)	C16—C17—C18—C19	1.1 (5)
C1—N2—C8—C13	123.8 (4)	Cl1—C17—C18—C19	−179.7 (3)
C2—N2—C8—C13	−62.2 (4)	C17—C18—C19—C20	0.5 (5)
C1—N2—C8—C9	−58.6 (4)	C18—C19—C20—C15	−0.8 (5)
C2—N2—C8—C9	115.4 (4)	C16—C15—C20—C19	−0.5 (5)
C13—C8—C9—C10	−2.0 (5)	C14—C15—C20—C19	−178.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1i	0.90 (2)	2.48 (3)	3.351 (4)	162 (2)
C13—H13A···O1ii	0.95	2.59	3.434 (5)	148
C18—H18A···S1iii	0.95	2.87	3.609 (5)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S1i	0.90 (2)	2.48 (3)	3.351 (4)	162 (2)
C13—H13A⋯O1ii	0.95	2.59	3.434 (5)	148
C18—H18A⋯S1iii	0.95	2.87	3.609 (5)	136

Symmetry codes: (i) ; (ii) ; (iii) .