1,1-Dibenzyl-3-(3-chloro-benzo-yl)thio-urea.

In the title compound, C(22)H(19)ClN(2)OS, the thiono and carbonyl groups are trans positioned with respect to a partially double C-N bond. The amide group is twisted relative to the thio-urea fragment, forming a dihedral angle of 46.75 (11)°. In the crystal, inter-molecular N-H⋯S and C-H⋯O hydrogen bonds link the mol-ecules into a one-dimensional polymeric structure parallel to the c axis.

Related literature

For related structures and background references, see: Al-abbasi & Kassim (2011 ▶); Nasir et al. (2011 ▶). For metal complexes of benzoyl­thio­ureas, see: Weiqun et al. (2005 ▶); Circu et al. (2009 ▶). For the synthetic procedure, see: Hassan et al. (2008 ▶).

Experimental

Crystal data

C22H19ClN2OS

M = 394.90

Triclinic,

a = 9.503 (4) Å

b = 9.650 (4) Å

c = 12.487 (5) Å

α = 72.422 (8)°

β = 72.869 (9)°

γ = 69.463 (8)°

V = 999.1 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.31 mm−1

T = 298 K

0.28 × 0.17 × 0.13 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.918, T max = 0.961

13666 measured reflections

5000 independent reflections

2879 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.147

S = 1.03

5000 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811023191/gk2383sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023191/gk2383Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811023191/gk2383Isup3.cml

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

C22H19ClN2OS	Z = 2
Mr = 394.90	F(000) = 412
Triclinic, P1	Dx = 1.313 Mg m−3
Hall symbol: -P 1	Melting point: 409.15 K
a = 9.503 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.650 (4) Å	Cell parameters from 1114 reflections
c = 12.487 (5) Å	θ = 2.3–28.5°
α = 72.422 (8)°	µ = 0.31 mm−1
β = 72.869 (9)°	T = 298 K
γ = 69.463 (8)°	Block, colourless
V = 999.1 (7) Å3	0.28 × 0.17 × 0.13 mm

Bruker SMART APEX CCD area-detector diffractometer	5000 independent reflections
Radiation source: fine-focus sealed tube	2879 reflections with I > 2σ(I)
graphite	Rint = 0.036
ω scans	θmax = 28.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −12→12
Tmin = 0.918, Tmax = 0.961	k = −12→12
13666 measured reflections	l = −16→16

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0679P)2 + 0.0522P] where P = (Fo2 + 2Fc2)/3
5000 reflections	(Δ/σ)max = 0.001
244 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

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	0.89445 (7)	0.70137 (6)	0.39746 (5)	0.0651 (2)
Cl1	1.24059 (9)	−0.15952 (8)	0.53858 (7)	0.0984 (3)
O1	1.15882 (17)	0.42880 (17)	0.15716 (13)	0.0614 (4)
N1	1.01426 (17)	0.43643 (17)	0.33839 (14)	0.0475 (4)
H1	0.9940	0.3826	0.4067	0.057*
N2	0.86120 (18)	0.62690 (17)	0.21995 (14)	0.0474 (4)
C8	0.9214 (2)	0.5863 (2)	0.31191 (17)	0.0454 (5)
C1	1.2465 (2)	0.2283 (2)	0.30830 (18)	0.0476 (5)
C7	1.1378 (2)	0.3712 (2)	0.25868 (19)	0.0482 (5)
C6	1.1962 (2)	0.1167 (2)	0.39517 (18)	0.0517 (5)
H6	1.0920	0.1315	0.4278	0.062*
C10	0.6590 (2)	0.5487 (2)	0.19232 (18)	0.0502 (5)
C9	0.8302 (2)	0.5205 (2)	0.1730 (2)	0.0541 (5)
H9A	0.8767	0.4170	0.2104	0.065*
H9B	0.8751	0.5338	0.0914	0.065*
C16	0.7941 (2)	0.7885 (2)	0.17143 (19)	0.0542 (5)
H16A	0.8138	0.8494	0.2115	0.065*
H16B	0.6835	0.8095	0.1842	0.065*
C17	0.8578 (3)	0.8343 (2)	0.04457 (19)	0.0569 (6)
C5	1.3029 (3)	−0.0172 (2)	0.43277 (19)	0.0607 (6)
C15	0.5883 (3)	0.5901 (3)	0.1013 (2)	0.0658 (6)
H15	0.6472	0.5954	0.0269	0.079*
C4	1.4577 (3)	−0.0385 (3)	0.3883 (2)	0.0708 (7)
H4	1.5287	−0.1283	0.4150	0.085*
C2	1.4025 (2)	0.2061 (2)	0.2627 (2)	0.0633 (6)
H2	1.4370	0.2804	0.2039	0.076*
C3	1.5060 (3)	0.0740 (3)	0.3045 (2)	0.0751 (8)
H3	1.6107	0.0609	0.2752	0.090*
C22	1.0129 (3)	0.7936 (3)	−0.0005 (2)	0.0719 (7)
H22	1.0805	0.7298	0.0466	0.086*
C11	0.5686 (3)	0.5384 (3)	0.3020 (2)	0.0741 (7)
H11	0.6143	0.5088	0.3649	0.089*
C18	0.7596 (4)	0.9279 (3)	−0.0270 (2)	0.0797 (8)
H18	0.6540	0.9551	0.0021	0.096*
C14	0.4304 (3)	0.6240 (3)	0.1196 (3)	0.0860 (8)
H14	0.3838	0.6519	0.0573	0.103*
C21	1.0691 (4)	0.8466 (4)	−0.1150 (3)	0.0994 (11)
H21	1.1744	0.8176	−0.1449	0.119*
C19	0.8167 (6)	0.9815 (4)	−0.1415 (3)	0.1121 (13)
H19	0.7500	1.0453	−0.1893	0.135*
C20	0.9722 (7)	0.9406 (4)	−0.1848 (3)	0.1165 (15)
H20	1.0111	0.9774	−0.2619	0.140*
C12	0.4102 (4)	0.5717 (4)	0.3194 (3)	0.0922 (9)
H12	0.3504	0.5633	0.3936	0.111*
C13	0.3428 (3)	0.6166 (3)	0.2279 (4)	0.0907 (10)
H13	0.2364	0.6424	0.2393	0.109*

	U11	U22	U33	U12	U13	U23
S1	0.0793 (4)	0.0510 (3)	0.0616 (4)	0.0073 (3)	−0.0289 (3)	−0.0249 (3)
Cl1	0.0963 (6)	0.0616 (4)	0.0962 (5)	−0.0036 (4)	−0.0078 (4)	0.0053 (4)
O1	0.0552 (9)	0.0614 (9)	0.0517 (9)	−0.0035 (7)	−0.0041 (7)	−0.0128 (7)
N1	0.0469 (9)	0.0392 (8)	0.0447 (9)	0.0005 (7)	−0.0070 (8)	−0.0106 (7)
N2	0.0481 (9)	0.0393 (9)	0.0529 (10)	−0.0012 (7)	−0.0168 (8)	−0.0152 (8)
C8	0.0391 (10)	0.0428 (11)	0.0480 (11)	−0.0037 (8)	−0.0078 (9)	−0.0122 (9)
C1	0.0418 (11)	0.0433 (11)	0.0541 (12)	−0.0008 (9)	−0.0097 (9)	−0.0197 (9)
C7	0.0428 (11)	0.0468 (11)	0.0532 (13)	−0.0074 (9)	−0.0068 (9)	−0.0181 (10)
C6	0.0427 (11)	0.0502 (12)	0.0567 (13)	−0.0010 (9)	−0.0083 (10)	−0.0210 (10)
C10	0.0497 (12)	0.0441 (11)	0.0553 (12)	−0.0084 (9)	−0.0111 (10)	−0.0149 (9)
C9	0.0539 (12)	0.0463 (11)	0.0630 (13)	−0.0027 (10)	−0.0180 (11)	−0.0217 (10)
C16	0.0556 (13)	0.0414 (11)	0.0614 (13)	0.0017 (9)	−0.0216 (11)	−0.0149 (10)
C17	0.0731 (15)	0.0413 (11)	0.0611 (14)	−0.0108 (11)	−0.0246 (12)	−0.0147 (10)
C5	0.0633 (15)	0.0476 (12)	0.0619 (14)	−0.0004 (10)	−0.0125 (11)	−0.0180 (11)
C15	0.0576 (14)	0.0784 (17)	0.0654 (15)	−0.0165 (12)	−0.0158 (12)	−0.0224 (13)
C4	0.0574 (15)	0.0530 (14)	0.0874 (18)	0.0118 (12)	−0.0208 (14)	−0.0226 (13)
C2	0.0465 (12)	0.0501 (13)	0.0797 (16)	−0.0031 (10)	−0.0024 (11)	−0.0187 (12)
C3	0.0410 (13)	0.0644 (16)	0.106 (2)	0.0039 (11)	−0.0051 (13)	−0.0322 (16)
C22	0.0767 (18)	0.0659 (16)	0.0727 (17)	−0.0243 (14)	−0.0109 (14)	−0.0150 (13)
C11	0.0800 (18)	0.0793 (18)	0.0590 (15)	−0.0218 (15)	−0.0077 (13)	−0.0176 (13)
C18	0.110 (2)	0.0598 (15)	0.0720 (18)	−0.0091 (15)	−0.0449 (16)	−0.0109 (13)
C14	0.0605 (17)	0.101 (2)	0.108 (2)	−0.0165 (15)	−0.0323 (17)	−0.0332 (19)
C21	0.128 (3)	0.087 (2)	0.086 (2)	−0.058 (2)	0.019 (2)	−0.0300 (19)
C19	0.203 (4)	0.071 (2)	0.069 (2)	−0.033 (3)	−0.059 (3)	−0.0023 (17)
C20	0.221 (5)	0.078 (2)	0.060 (2)	−0.074 (3)	−0.007 (3)	−0.0133 (17)
C12	0.079 (2)	0.097 (2)	0.095 (2)	−0.0399 (18)	0.0271 (18)	−0.0401 (18)
C13	0.0533 (16)	0.085 (2)	0.144 (3)	−0.0193 (14)	−0.009 (2)	−0.051 (2)

S1—C8	1.672 (2)	C5—C4	1.375 (3)
Cl1—C5	1.731 (3)	C15—C14	1.382 (4)
O1—C7	1.208 (3)	C15—H15	0.9300
N1—C7	1.392 (2)	C4—C3	1.365 (3)
N1—C8	1.402 (2)	C4—H4	0.9300
N1—H1	0.8600	C2—C3	1.373 (3)
N2—C8	1.326 (2)	C2—H2	0.9300
N2—C9	1.470 (3)	C3—H3	0.9300
N2—C16	1.471 (2)	C22—C21	1.375 (4)
C1—C6	1.384 (3)	C22—H22	0.9300
C1—C2	1.386 (3)	C11—C12	1.388 (4)
C1—C7	1.488 (3)	C11—H11	0.9300
C6—C5	1.383 (3)	C18—C19	1.377 (4)
C6—H6	0.9300	C18—H18	0.9300
C10—C15	1.374 (3)	C14—C13	1.359 (4)
C10—C11	1.382 (3)	C14—H14	0.9300
C10—C9	1.508 (3)	C21—C20	1.356 (5)
C9—H9A	0.9700	C21—H21	0.9300
C9—H9B	0.9700	C19—C20	1.371 (6)
C16—C17	1.507 (3)	C19—H19	0.9300
C16—H16A	0.9700	C20—H20	0.9300
C16—H16B	0.9700	C12—C13	1.357 (5)
C17—C22	1.372 (3)	C12—H12	0.9300
C17—C18	1.378 (3)	C13—H13	0.9300
C7—N1—C8	122.70 (17)	C10—C15—C14	120.6 (2)
C7—N1—H1	118.6	C10—C15—H15	119.7
C8—N1—H1	118.6	C14—C15—H15	119.7
C8—N2—C9	123.98 (17)	C3—C4—C5	119.2 (2)
C8—N2—C16	120.06 (17)	C3—C4—H4	120.4
C9—N2—C16	115.01 (16)	C5—C4—H4	120.4
N2—C8—N1	117.33 (17)	C3—C2—C1	119.8 (2)
N2—C8—S1	124.47 (15)	C3—C2—H2	120.1
N1—C8—S1	118.19 (14)	C1—C2—H2	120.1
C6—C1—C2	119.73 (19)	C4—C3—C2	121.1 (2)
C6—C1—C7	122.07 (18)	C4—C3—H3	119.5
C2—C1—C7	118.2 (2)	C2—C3—H3	119.5
O1—C7—N1	122.69 (19)	C17—C22—C21	120.4 (3)
O1—C7—C1	122.22 (18)	C17—C22—H22	119.8
N1—C7—C1	115.04 (18)	C21—C22—H22	119.8
C5—C6—C1	119.1 (2)	C10—C11—C12	120.7 (3)
C5—C6—H6	120.4	C10—C11—H11	119.7
C1—C6—H6	120.4	C12—C11—H11	119.7
C15—C10—C11	118.3 (2)	C19—C18—C17	120.4 (3)
C15—C10—C9	121.0 (2)	C19—C18—H18	119.8
C11—C10—C9	120.7 (2)	C17—C18—H18	119.8
N2—C9—C10	109.86 (16)	C13—C14—C15	120.4 (3)
N2—C9—H9A	109.7	C13—C14—H14	119.8
C10—C9—H9A	109.7	C15—C14—H14	119.8
N2—C9—H9B	109.7	C20—C21—C22	120.5 (3)
C10—C9—H9B	109.7	C20—C21—H21	119.7
H9A—C9—H9B	108.2	C22—C21—H21	119.7
N2—C16—C17	112.77 (16)	C20—C19—C18	119.9 (3)
N2—C16—H16A	109.0	C20—C19—H19	120.0
C17—C16—H16A	109.0	C18—C19—H19	120.0
N2—C16—H16B	109.0	C21—C20—C19	119.9 (3)
C17—C16—H16B	109.0	C21—C20—H20	120.1
H16A—C16—H16B	107.8	C19—C20—H20	120.1
C22—C17—C18	118.9 (2)	C13—C12—C11	119.9 (3)
C22—C17—C16	121.5 (2)	C13—C12—H12	120.1
C18—C17—C16	119.5 (2)	C11—C12—H12	120.1
C4—C5—C6	121.1 (2)	C12—C13—C14	120.2 (3)
C4—C5—Cl1	119.47 (18)	C12—C13—H13	119.9
C6—C5—Cl1	119.44 (18)	C14—C13—H13	119.9
C9—N2—C8—N1	26.1 (3)	C1—C6—C5—Cl1	−178.21 (16)
C16—N2—C8—N1	−165.58 (17)	C11—C10—C15—C14	1.5 (4)
C9—N2—C8—S1	−154.11 (16)	C9—C10—C15—C14	−176.4 (2)
C16—N2—C8—S1	14.2 (3)	C6—C5—C4—C3	−1.0 (4)
C7—N1—C8—N2	52.4 (3)	Cl1—C5—C4—C3	179.7 (2)
C7—N1—C8—S1	−127.36 (18)	C6—C1—C2—C3	−0.4 (3)
C8—N1—C7—O1	−12.5 (3)	C7—C1—C2—C3	−178.5 (2)
C8—N1—C7—C1	164.86 (17)	C5—C4—C3—C2	−1.2 (4)
C6—C1—C7—O1	−140.7 (2)	C1—C2—C3—C4	1.9 (4)
C2—C1—C7—O1	37.3 (3)	C18—C17—C22—C21	0.5 (4)
C6—C1—C7—N1	41.9 (3)	C16—C17—C22—C21	−174.9 (2)
C2—C1—C7—N1	−140.1 (2)	C15—C10—C11—C12	−1.1 (4)
C2—C1—C6—C5	−1.7 (3)	C9—C10—C11—C12	176.8 (2)
C7—C1—C6—C5	176.25 (19)	C22—C17—C18—C19	−1.0 (4)
C8—N2—C9—C10	110.5 (2)	C16—C17—C18—C19	174.5 (2)
C16—N2—C9—C10	−58.3 (2)	C10—C15—C14—C13	0.0 (4)
C15—C10—C9—N2	119.3 (2)	C17—C22—C21—C20	0.5 (4)
C11—C10—C9—N2	−58.6 (3)	C17—C18—C19—C20	0.5 (5)
C8—N2—C16—C17	127.7 (2)	C22—C21—C20—C19	−1.1 (5)
C9—N2—C16—C17	−63.0 (2)	C18—C19—C20—C21	0.6 (5)
N2—C16—C17—C22	−47.3 (3)	C10—C11—C12—C13	−0.7 (4)
N2—C16—C17—C18	137.3 (2)	C11—C12—C13—C14	2.3 (5)
C1—C6—C5—C4	2.5 (3)	C15—C14—C13—C12	−1.9 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···S1	0.97	2.51	3.029 (3)	113
N1—H1···S1i	0.86	2.74	3.410 (2)	136
C15—H15···O1ii	0.93	2.50	3.421 (3)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S1i	0.86	2.74	3.410 (2)	136
C15—H15⋯O1ii	0.93	2.50	3.421 (3)	170

Symmetry codes: (i) ; (ii) .