1-(4-Bromo-phen-yl)-3-(3-chloro-propan-oyl)thio-urea.

The title compound, C10H10BrClN2OS, adopts a trans-cis conformation with respect to the position of the 3-chloro-propanoyl and 4-bromo-phenyl groups, respectively, against the thiono C=S bond across their C-N bonds. The benzene ring makes a dihedral angle of 9.55 (16)° with the N2CS thio-urea moiety. Intra-molecular N-H⋯O and C-H⋯S hydrogen bonds occur. In the crystal, mol-ecules are linked into chains along the c-axis direction by N-H⋯S, C-H⋯S and C-H⋯O hydrogen bonds.

Related literature

For the crystal structures of related compounds, see: Othman et al. (2010 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C10H10BrClN2OS

M = 321.62

Triclinic,

a = 5.3899 (4) Å

b = 8.3705 (5) Å

c = 13.7369 (8) Å

α = 91.209 (2)°

β = 96.417 (2)°

γ = 92.731 (2)°

V = 614.96 (7) Å3

Z = 2

Mo Kα radiation

μ = 3.71 mm−1

T = 296 K

0.46 × 0.45 × 0.15 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.280, T max = 0.606

11958 measured reflections

2405 independent reflections

2053 reflections with I > 2σ(I)

R int = 0.129

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.111

S = 1.11

2405 reflections

154 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.67 e Å−3

Data collection: SMART (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814011209/rk2427sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814011209/rk2427Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814011209/rk2427Isup3.cml

CCDC reference: 1003286

Additional supporting information: crystallographic information; 3D view; checkCIF report

C10H10BrClN2OS	Z = 2
Mr = 321.62	F(000) = 320
Triclinic, P1	Dx = 1.737 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.3899 (4) Å	Cell parameters from 7910 reflections
b = 8.3705 (5) Å	θ = 2.9–25.9°
c = 13.7369 (8) Å	µ = 3.71 mm−1
α = 91.209 (2)°	T = 296 K
β = 96.417 (2)°	Block, colourless
γ = 92.731 (2)°	0.46 × 0.45 × 0.15 mm
V = 614.96 (7) Å3

Bruker SMART APEX CCD diffractometer	2405 independent reflections
Radiation source: fine-focus sealed tube	2053 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.129
Detector resolution: 83.66 pixels mm-1	θmax = 26.0°, θmin = 3.0°
ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −10→10
Tmin = 0.280, Tmax = 0.606	l = −16→16
11958 measured reflections

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)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.111	w = 1/[σ2(Fo2) + (0.0381P)2 + 0.5365P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max = 0.001
2405 reflections	Δρmax = 0.44 e Å−3
154 parameters	Δρmin = −0.67 e Å−3
2 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: 0.067 (5)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
Br1	0.28574 (8)	0.63531 (5)	1.11594 (3)	0.0559 (2)
Cl1	0.8887 (2)	1.50961 (14)	0.64873 (11)	0.0707 (4)
S1	0.40834 (18)	0.83621 (11)	0.60404 (6)	0.0447 (3)
O1	1.0855 (5)	1.1309 (3)	0.74807 (18)	0.0481 (7)
N1	0.7900 (5)	1.0463 (3)	0.6239 (2)	0.0348 (6)
N2	0.7069 (6)	0.9295 (4)	0.7667 (2)	0.0387 (7)
C1	1.1700 (7)	1.4130 (4)	0.6359 (3)	0.0457 (9)
H1A	1.2690	1.4749	0.5939	0.055*
H1B	1.2667	1.4073	0.6996	0.055*
C2	1.1149 (7)	1.2461 (4)	0.5923 (3)	0.0429 (9)
H2A	1.2689	1.2024	0.5759	0.051*
H2B	1.0022	1.2509	0.5324	0.051*
C3	0.9979 (7)	1.1373 (4)	0.6630 (3)	0.0371 (8)
C4	0.6423 (6)	0.9385 (4)	0.6716 (2)	0.0313 (7)
C5	0.5977 (6)	0.8495 (4)	0.8422 (2)	0.0332 (7)
C6	0.3732 (7)	0.7605 (5)	0.8312 (3)	0.0450 (9)
H6	0.2838	0.7447	0.7695	0.054*
C7	0.2820 (7)	0.6947 (5)	0.9131 (3)	0.0452 (9)
H7	0.1311	0.6347	0.9066	0.054*
C8	0.4156 (7)	0.7187 (4)	1.0035 (3)	0.0382 (8)
C9	0.6388 (7)	0.8042 (5)	1.0150 (3)	0.0485 (9)
H9	0.7287	0.8193	1.0766	0.058*
C10	0.7283 (7)	0.8680 (5)	0.9334 (3)	0.0481 (10)
H10	0.8818	0.9251	0.9405	0.058*
H1	0.742 (7)	1.058 (5)	0.5620 (10)	0.041 (10)*
H2	0.835 (5)	0.990 (4)	0.791 (3)	0.057 (13)*

	U11	U22	U33	U12	U13	U23
Br1	0.0605 (3)	0.0655 (3)	0.0444 (3)	−0.0072 (2)	0.0209 (2)	0.0123 (2)
Cl1	0.0667 (7)	0.0585 (7)	0.0908 (9)	0.0081 (6)	0.0226 (6)	0.0126 (6)
S1	0.0513 (6)	0.0445 (5)	0.0338 (5)	−0.0216 (4)	−0.0061 (4)	0.0080 (4)
O1	0.0475 (15)	0.0584 (16)	0.0349 (14)	−0.0235 (13)	−0.0007 (11)	0.0039 (12)
N1	0.0375 (15)	0.0362 (14)	0.0288 (14)	−0.0128 (12)	0.0007 (12)	0.0049 (12)
N2	0.0387 (16)	0.0433 (16)	0.0315 (15)	−0.0178 (13)	0.0003 (12)	0.0068 (12)
C1	0.043 (2)	0.0406 (19)	0.052 (2)	−0.0126 (16)	0.0040 (17)	0.0059 (17)
C2	0.041 (2)	0.046 (2)	0.041 (2)	−0.0149 (16)	0.0104 (16)	0.0050 (16)
C3	0.0387 (19)	0.0356 (17)	0.0367 (19)	−0.0070 (14)	0.0072 (15)	0.0016 (14)
C4	0.0354 (17)	0.0270 (15)	0.0308 (16)	−0.0041 (13)	0.0025 (13)	0.0032 (12)
C5	0.0355 (17)	0.0333 (16)	0.0303 (16)	−0.0046 (14)	0.0031 (13)	0.0057 (13)
C6	0.045 (2)	0.051 (2)	0.0366 (19)	−0.0174 (17)	0.0007 (15)	0.0018 (16)
C7	0.042 (2)	0.050 (2)	0.042 (2)	−0.0175 (17)	0.0049 (16)	0.0050 (17)
C8	0.0416 (19)	0.0400 (18)	0.0353 (18)	0.0004 (15)	0.0137 (15)	0.0062 (14)
C9	0.046 (2)	0.065 (2)	0.0323 (18)	−0.0089 (19)	−0.0012 (16)	0.0070 (17)
C10	0.039 (2)	0.066 (2)	0.036 (2)	−0.0209 (18)	−0.0008 (15)	0.0054 (18)

Br1—C8	1.898 (3)	C2—C3	1.514 (4)
Cl1—C1	1.776 (4)	C2—H2A	0.9700
S1—C4	1.669 (3)	C2—H2B	0.9700
O1—C3	1.213 (4)	C5—C10	1.369 (5)
N1—C3	1.375 (4)	C5—C6	1.382 (5)
N1—C4	1.397 (4)	C6—C7	1.391 (5)
N1—H1	0.869 (10)	C6—H6	0.9300
N2—C4	1.319 (4)	C7—C8	1.370 (5)
N2—C5	1.414 (4)	C7—H7	0.9300
N2—H2	0.864 (10)	C8—C9	1.362 (5)
C1—C2	1.511 (5)	C9—C10	1.376 (5)
C1—H1A	0.9700	C9—H9	0.9300
C1—H1B	0.9700	C10—H10	0.9300
C3—N1—C4	128.1 (3)	N2—C4—N1	114.9 (3)
C3—N1—H1	117 (2)	N2—C4—S1	127.4 (2)
C4—N1—H1	115 (2)	N1—C4—S1	117.7 (2)
C4—N2—C5	133.1 (3)	C10—C5—C6	119.1 (3)
C4—N2—H2	116 (3)	C10—C5—N2	115.2 (3)
C5—N2—H2	111 (3)	C6—C5—N2	125.7 (3)
C2—C1—Cl1	110.8 (3)	C5—C6—C7	119.4 (3)
C2—C1—H1A	109.5	C5—C6—H6	120.3
Cl1—C1—H1A	109.5	C7—C6—H6	120.3
C2—C1—H1B	109.5	C8—C7—C6	119.7 (3)
Cl1—C1—H1B	109.5	C8—C7—H7	120.1
H1A—C1—H1B	108.1	C6—C7—H7	120.1
C1—C2—C3	111.3 (3)	C9—C8—C7	121.3 (3)
C1—C2—H2A	109.4	C9—C8—Br1	118.9 (3)
C3—C2—H2A	109.4	C7—C8—Br1	119.7 (3)
C1—C2—H2B	109.4	C8—C9—C10	118.6 (4)
C3—C2—H2B	109.4	C8—C9—H9	120.7
H2A—C2—H2B	108.0	C10—C9—H9	120.7
O1—C3—N1	123.0 (3)	C5—C10—C9	121.8 (3)
O1—C3—C2	121.5 (3)	C5—C10—H10	119.1
N1—C3—C2	115.5 (3)	C9—C10—H10	119.1
Cl1—C1—C2—C3	−68.4 (4)	C10—C5—C6—C7	1.4 (6)
C4—N1—C3—O1	2.0 (6)	N2—C5—C6—C7	−176.8 (4)
C4—N1—C3—C2	−178.8 (3)	C5—C6—C7—C8	−0.1 (6)
C1—C2—C3—O1	−47.9 (5)	C6—C7—C8—C9	−0.9 (6)
C1—C2—C3—N1	132.9 (3)	C6—C7—C8—Br1	177.8 (3)
C5—N2—C4—N1	173.3 (4)	C7—C8—C9—C10	0.4 (6)
C5—N2—C4—S1	−6.9 (6)	Br1—C8—C9—C10	−178.3 (3)
C3—N1—C4—N2	3.1 (5)	C6—C5—C10—C9	−1.9 (7)
C3—N1—C4—S1	−176.7 (3)	N2—C5—C10—C9	176.5 (4)
C4—N2—C5—C10	178.7 (4)	C8—C9—C10—C5	1.0 (7)
C4—N2—C5—C6	−3.0 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.87 (3)	1.90 (3)	2.623 (4)	140 (4)
C6—H6···S1	0.93	2.56	3.222 (4)	128
N1—H1···S1i	0.87 (2)	2.53 (2)	3.376 (3)	166 (4)
C2—H2B···S1i	0.97	2.79	3.707 (4)	157
C9—H9···O1ii	0.93	2.52	3.444 (5)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.87 (3)	1.90 (3)	2.623 (4)	140 (4)
C6—H6⋯S1	0.93	2.56	3.222 (4)	128
N1—H1⋯S1i	0.87 (2)	2.53 (2)	3.376 (3)	166 (4)
C2—H2B⋯S1i	0.97	2.79	3.707 (4)	157
C9—H9⋯O1ii	0.93	2.52	3.444 (5)	172

Symmetry codes: (i) ; (ii) .