N-(3-Chloro-propion-yl)-N'-phenyl-thio-urea.

The title compound, C(10)H(11)ClN(2)OS, adopts a cis-trans configuration with respect to the position of the phenyl and 3-chloro-propionyl groups relative to the thiono group across the C-N bonds. The benzene ring is perpendicular to the propionyl thio-urea fragment with a dihedral angle of 82.62 (10)°. An intra-molecular N-H⋯O inter-action occurs. The crystal structure is stabilized by inter-molecular N-H⋯S hydrogen bonds, which link pairs of mol-ecules, building up R(2) (2)(8) ring motifs, and C-H.. π inter-actions.

Related literature

For related structures, see: Ismail et al. (2007 ▶); Ismail & Yamin (2009 ▶). For hydrogen-bond motifs, see: Etter et al.(1990 ▶); Bernstein et al. (1995 ▶). For reference bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C10H11ClN2OS

M = 242.72

Triclinic,

a = 5.8088 (12) Å

b = 10.467 (2) Å

c = 10.660 (2) Å

α = 112.811 (3)°

β = 101.855 (3)°

γ = 95.483 (3)°

V = 573.6 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.49 mm−1

T = 298 K

0.49 × 0.45 × 0.27 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.795, T max = 0.879

5617 measured reflections

2103 independent reflections

1798 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.113

S = 1.04

2103 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −0.43 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 datablocks global, I. DOI: 10.1107/S1600536810005271/dn2535sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810005271/dn2535Isup2.hkl

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

C10H11ClN2OS	Z = 2
Mr = 242.72	F(000) = 252
Triclinic, P1	Dx = 1.405 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.8088 (12) Å	Cell parameters from 3405 reflections
b = 10.467 (2) Å	θ = 2.1–25.5°
c = 10.660 (2) Å	µ = 0.49 mm−1
α = 112.811 (3)°	T = 298 K
β = 101.855 (3)°	Block, colourless
γ = 95.483 (3)°	0.49 × 0.45 × 0.27 mm
V = 573.6 (2) Å3

Bruker SMART APEX CCD area-detector diffractometer	2103 independent reflections
Radiation source: fine-focus sealed tube	1798 reflections with I > 2σ(I)
Detector resolution: 83.66 pixels mm-1	Rint = 0.016
ω scan	θmax = 25.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −7→7
Tmin = 0.795, Tmax = 0.879	k = −12→12
5617 measured reflections	l = −12→12

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0559P)2 + 0.2663P] where P = (Fo2 + 2Fc2)/3
2103 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.54 e Å−3
0 restraints	Δρmin = −0.43 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 > 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	0.23811 (13)	1.37819 (8)	0.50799 (7)	0.0777 (3)
S1	1.10045 (13)	0.86771 (7)	0.31949 (6)	0.0653 (2)
O1	0.5152 (3)	1.07380 (16)	0.16725 (14)	0.0539 (4)
N1	0.7823 (3)	1.03263 (18)	0.32922 (17)	0.0497 (4)
H1A	0.8413	1.0614	0.4186	0.060*
N2	0.7847 (3)	0.87565 (18)	0.10659 (17)	0.0484 (4)
H2A	0.6781	0.9154	0.0753	0.058*
C1	0.3405 (4)	1.2689 (3)	0.3640 (2)	0.0594 (6)
H1B	0.2091	1.1935	0.2967	0.071*
H1C	0.3931	1.3244	0.3167	0.071*
C2	0.5422 (4)	1.2067 (2)	0.4124 (2)	0.0539 (5)
H2B	0.4968	1.1623	0.4707	0.065*
H2C	0.6809	1.2815	0.4696	0.065*
C3	0.6079 (4)	1.0991 (2)	0.2902 (2)	0.0434 (5)
C4	0.8769 (4)	0.9252 (2)	0.2443 (2)	0.0452 (5)
C5	0.8541 (4)	0.7586 (2)	0.00691 (19)	0.0435 (5)
C6	1.0500 (4)	0.7804 (2)	−0.0412 (2)	0.0543 (5)
H6A	1.1404	0.8707	−0.0087	0.065*
C7	1.1101 (5)	0.6653 (3)	−0.1391 (3)	0.0618 (6)
H7A	1.2421	0.6787	−0.1725	0.074*
C8	0.9790 (5)	0.5329 (3)	−0.1872 (2)	0.0635 (7)
H8A	1.0221	0.4565	−0.2524	0.076*
C9	0.7837 (5)	0.5125 (2)	−0.1393 (3)	0.0646 (7)
H9A	0.6934	0.4221	−0.1724	0.078*
C10	0.7203 (4)	0.6258 (2)	−0.0418 (2)	0.0541 (5)
H10A	0.5872	0.6120	−0.0094	0.065*

	U11	U22	U33	U12	U13	U23
Cl1	0.0802 (5)	0.0871 (5)	0.0664 (4)	0.0432 (4)	0.0358 (4)	0.0181 (4)
S1	0.0877 (5)	0.0664 (4)	0.0387 (3)	0.0470 (3)	0.0082 (3)	0.0157 (3)
O1	0.0636 (9)	0.0576 (9)	0.0367 (8)	0.0276 (7)	0.0084 (7)	0.0145 (7)
N1	0.0632 (11)	0.0471 (10)	0.0316 (8)	0.0248 (8)	0.0058 (7)	0.0090 (7)
N2	0.0596 (11)	0.0462 (10)	0.0345 (9)	0.0255 (8)	0.0069 (7)	0.0110 (7)
C1	0.0641 (14)	0.0675 (15)	0.0476 (12)	0.0343 (12)	0.0188 (11)	0.0180 (11)
C2	0.0604 (13)	0.0556 (13)	0.0400 (11)	0.0260 (11)	0.0097 (10)	0.0126 (10)
C3	0.0480 (11)	0.0397 (10)	0.0384 (11)	0.0137 (9)	0.0082 (8)	0.0125 (8)
C4	0.0560 (12)	0.0387 (10)	0.0384 (10)	0.0162 (9)	0.0102 (9)	0.0130 (8)
C5	0.0524 (11)	0.0440 (11)	0.0313 (9)	0.0205 (9)	0.0066 (8)	0.0126 (8)
C6	0.0513 (12)	0.0552 (13)	0.0508 (12)	0.0123 (10)	0.0090 (10)	0.0182 (10)
C7	0.0600 (14)	0.0798 (18)	0.0559 (14)	0.0321 (13)	0.0245 (11)	0.0301 (13)
C8	0.0891 (18)	0.0620 (15)	0.0459 (13)	0.0419 (14)	0.0251 (12)	0.0194 (11)
C9	0.0920 (19)	0.0416 (12)	0.0555 (14)	0.0182 (12)	0.0218 (13)	0.0130 (10)
C10	0.0650 (14)	0.0484 (12)	0.0517 (12)	0.0169 (10)	0.0219 (11)	0.0192 (10)

Cl1—C1	1.778 (2)	C2—H2B	0.9700
S1—C4	1.669 (2)	C2—H2C	0.9700
O1—C3	1.221 (2)	C5—C10	1.369 (3)
N1—C3	1.367 (3)	C5—C6	1.375 (3)
N1—C4	1.386 (3)	C6—C7	1.385 (3)
N1—H1A	0.8600	C6—H6A	0.9300
N2—C4	1.320 (3)	C7—C8	1.361 (4)
N2—C5	1.433 (2)	C7—H7A	0.9300
N2—H2A	0.8600	C8—C9	1.367 (4)
C1—C2	1.490 (3)	C8—H8A	0.9300
C1—H1B	0.9700	C9—C10	1.381 (3)
C1—H1C	0.9700	C9—H9A	0.9300
C2—C3	1.503 (3)	C10—H10A	0.9300
C3—N1—C4	128.77 (17)	N2—C4—N1	117.03 (18)
C3—N1—H1A	115.6	N2—C4—S1	123.88 (16)
C4—N1—H1A	115.6	N1—C4—S1	119.09 (15)
C4—N2—C5	122.97 (17)	C10—C5—C6	120.60 (19)
C4—N2—H2A	118.5	C10—C5—N2	119.22 (19)
C5—N2—H2A	118.5	C6—C5—N2	120.17 (19)
C2—C1—Cl1	111.32 (16)	C5—C6—C7	118.7 (2)
C2—C1—H1B	109.4	C5—C6—H6A	120.7
Cl1—C1—H1B	109.4	C7—C6—H6A	120.7
C2—C1—H1C	109.4	C8—C7—C6	121.0 (2)
Cl1—C1—H1C	109.4	C8—C7—H7A	119.5
H1B—C1—H1C	108.0	C6—C7—H7A	119.5
C1—C2—C3	111.71 (17)	C7—C8—C9	119.9 (2)
C1—C2—H2B	109.3	C7—C8—H8A	120.1
C3—C2—H2B	109.3	C9—C8—H8A	120.1
C1—C2—H2C	109.3	C8—C9—C10	120.1 (2)
C3—C2—H2C	109.3	C8—C9—H9A	119.9
H2B—C2—H2C	107.9	C10—C9—H9A	119.9
O1—C3—N1	122.97 (18)	C5—C10—C9	119.7 (2)
O1—C3—C2	123.17 (18)	C5—C10—H10A	120.1
N1—C3—C2	113.86 (17)	C9—C10—H10A	120.1
Cl1—C1—C2—C3	172.29 (17)	C4—N2—C5—C6	−86.1 (3)
C4—N1—C3—O1	−3.2 (4)	C10—C5—C6—C7	−0.5 (3)
C4—N1—C3—C2	177.1 (2)	N2—C5—C6—C7	−179.04 (19)
C1—C2—C3—O1	4.3 (3)	C5—C6—C7—C8	−0.1 (3)
C1—C2—C3—N1	−176.1 (2)	C6—C7—C8—C9	0.4 (4)
C5—N2—C4—N1	−175.79 (19)	C7—C8—C9—C10	−0.3 (4)
C5—N2—C4—S1	5.2 (3)	C6—C5—C10—C9	0.6 (3)
C3—N1—C4—N2	−2.1 (3)	N2—C5—C10—C9	179.2 (2)
C3—N1—C4—S1	176.94 (18)	C8—C9—C10—C5	−0.2 (4)
C4—N2—C5—C10	95.3 (3)

Cg1 is the centroid of the C5–C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	2.01	2.677 (3)	134
N1—H1A···S1i	0.86	2.53	3.3709 (19)	165
C1—H1C···Cg1ii	0.97	2.84	3.466	123

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C5–C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1	0.86	2.01	2.677 (3)	134
N1—H1A⋯S1i	0.86	2.53	3.3709 (19)	165
C1—H1C⋯Cg1ii	0.97	2.84	3.466	123

Symmetry codes: (i) ; (ii) .