N-(2-Bromo-phen-yl)thio-urea.

In the title compound, C(7)H(7)BrN(2)S, the thio-urea unit is almost perpendicular to the bromo-benzene fragment, making a dihedral angle of 80.82 (16)°. The crystal structure is stabilized by N-H⋯S inter-molecular hydrogen bonds, which form linear chains along the ab diagonal.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Steiner (1998 ▶); Shen & Xu (2004 ▶); Wang et al. (1991 ▶). For the anti­viral activity of phenyl­thio­ureas, see: D’Cruz & Uckun (2005 ▶); Frank & Smith (1955 ▶); Mao et al. (2000 ▶); Sudbeck et al. (1998 ▶).

Experimental

Crystal data

C7H7BrN2S

M = 231.12

Monoclinic,

a = 15.181 (3) Å

b = 7.7952 (16) Å

c = 15.312 (3) Å

β = 90.803 (4)°

V = 1811.8 (6) Å3

Z = 8

Mo Kα radiation

μ = 4.71 mm−1

T = 298 K

0.44 × 0.27 × 0.11 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.231, T max = 0.625

5817 measured reflections

1972 independent reflections

1327 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.129

S = 1.06

1972 reflections

100 parameters

H-atom parameters constrained

Δρmax = 0.61 e Å−3

Δρmin = −0.65 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: ORTEP-32 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶), PARST (Nardelli, 1995 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810008305/dn2543sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810008305/dn2543Isup2.hkl

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

C7H7BrN2S	F(000) = 912
Mr = 231.12	Dx = 1.695 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1400 reflections
a = 15.181 (3) Å	θ = 2.6–27.0°
b = 7.7952 (16) Å	µ = 4.71 mm−1
c = 15.312 (3) Å	T = 298 K
β = 90.803 (4)°	Block, colourless
V = 1811.8 (6) Å3	0.44 × 0.27 × 0.11 mm
Z = 8

Bruker SMART APEX CCD area-detector diffractometer	1972 independent reflections
Radiation source: fine-focus sealed tube	1327 reflections with I > 2σ(I)
graphite	Rint = 0.028
Detector resolution: 83.66 pixels mm-1	θmax = 27.0°, θmin = 2.6°
ω scan	h = −19→19
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −5→9
Tmin = 0.231, Tmax = 0.625	l = −19→19
5817 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0664P)2 + 1.1624P] where P = (Fo2 + 2Fc2)/3
1972 reflections	(Δ/σ)max < 0.001
100 parameters	Δρmax = 0.61 e Å−3
0 restraints	Δρmin = −0.65 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
Br1	0.10527 (4)	1.16677 (8)	0.59724 (3)	0.0909 (3)
S1	0.13874 (6)	0.57559 (13)	0.47185 (6)	0.0488 (3)
N1	0.16731 (19)	0.7869 (4)	0.60361 (19)	0.0498 (8)
H1A	0.2173	0.7961	0.5790	0.060*
N2	0.0356 (2)	0.6495 (5)	0.6038 (2)	0.0660 (11)
H2A	−0.0030	0.5879	0.5780	0.079*
H2B	0.0218	0.7159	0.6460	0.079*
C1	0.1703 (3)	0.7627 (6)	0.7636 (3)	0.0565 (10)
H1	0.1868	0.6482	0.7587	0.068*
C2	0.1620 (3)	0.8362 (6)	0.8439 (3)	0.0648 (12)
H2	0.1754	0.7731	0.8939	0.078*
C3	0.1338 (3)	1.0031 (7)	0.8512 (3)	0.0661 (12)
H3	0.1267	1.0510	0.9063	0.079*
C4	0.1163 (3)	1.0993 (6)	0.7788 (3)	0.0645 (11)
H4	0.0972	1.2122	0.7845	0.077*
C5	0.1267 (2)	1.0289 (5)	0.6969 (2)	0.0511 (9)
C6	0.1536 (2)	0.8622 (5)	0.6873 (2)	0.0447 (9)
C7	0.1116 (2)	0.6777 (4)	0.5653 (2)	0.0422 (8)

	U11	U22	U33	U12	U13	U23
Br1	0.1262 (6)	0.0874 (4)	0.0595 (3)	0.0326 (3)	0.0145 (3)	0.0182 (3)
S1	0.0499 (5)	0.0498 (5)	0.0472 (5)	−0.0151 (4)	0.0139 (4)	−0.0146 (4)
N1	0.0425 (17)	0.0608 (19)	0.0465 (17)	−0.0151 (15)	0.0159 (14)	−0.0186 (15)
N2	0.0445 (18)	0.087 (3)	0.067 (2)	−0.0264 (18)	0.0218 (16)	−0.036 (2)
C1	0.052 (2)	0.057 (2)	0.060 (2)	0.004 (2)	0.0012 (19)	−0.008 (2)
C2	0.072 (3)	0.077 (3)	0.045 (2)	−0.010 (2)	0.005 (2)	0.007 (2)
C3	0.080 (3)	0.076 (3)	0.042 (2)	−0.014 (3)	0.011 (2)	−0.013 (2)
C4	0.084 (3)	0.056 (2)	0.054 (2)	0.001 (2)	0.016 (2)	−0.014 (2)
C5	0.056 (2)	0.055 (2)	0.0418 (19)	−0.0019 (19)	0.0074 (17)	−0.0036 (17)
C6	0.0402 (19)	0.054 (2)	0.0403 (19)	−0.0100 (17)	0.0091 (15)	−0.0098 (16)
C7	0.0391 (19)	0.044 (2)	0.0440 (18)	−0.0072 (15)	0.0077 (15)	−0.0072 (15)

Br1—C5	1.891 (4)	C1—C6	1.421 (6)
S1—C7	1.693 (4)	C1—H1	0.9300
N1—C7	1.331 (4)	C2—C3	1.375 (7)
N1—C6	1.428 (4)	C2—H2	0.9300
N1—H1A	0.8551	C3—C4	1.361 (6)
N2—C7	1.320 (4)	C3—H3	0.9300
N2—H2A	0.8506	C4—C5	1.380 (5)
N2—H2B	0.8562	C4—H4	0.9300
C1—C2	1.364 (6)	C5—C6	1.371 (5)
C7—N1—C6	124.0 (3)	C2—C3—H3	119.6
C7—N1—H1A	115.0	C3—C4—C5	119.8 (4)
C6—N1—H1A	120.1	C3—C4—H4	120.1
C7—N2—H2A	119.1	C5—C4—H4	120.1
C7—N2—H2B	117.4	C6—C5—C4	120.8 (4)
H2A—N2—H2B	121.2	C6—C5—Br1	120.0 (3)
C2—C1—C6	119.6 (4)	C4—C5—Br1	119.1 (3)
C2—C1—H1	120.2	C5—C6—C1	118.6 (3)
C6—C1—H1	120.2	C5—C6—N1	122.2 (4)
C1—C2—C3	120.2 (4)	C1—C6—N1	119.1 (3)
C1—C2—H2	119.9	N2—C7—N1	117.6 (3)
C3—C2—H2	119.9	N2—C7—S1	121.6 (3)
C4—C3—C2	120.9 (4)	N1—C7—S1	120.8 (3)
C4—C3—H3	119.6
C6—C1—C2—C3	2.9 (6)	Br1—C5—C6—N1	0.6 (5)
C1—C2—C3—C4	−1.9 (7)	C2—C1—C6—C5	−2.1 (6)
C2—C3—C4—C5	0.0 (7)	C2—C1—C6—N1	176.5 (4)
C3—C4—C5—C6	0.8 (6)	C7—N1—C6—C5	−103.7 (4)
C3—C4—C5—Br1	−178.2 (3)	C7—N1—C6—C1	77.7 (5)
C4—C5—C6—C1	0.2 (6)	C6—N1—C7—N2	6.2 (6)
Br1—C5—C6—C1	179.2 (3)	C6—N1—C7—S1	−172.3 (3)
C4—C5—C6—N1	−178.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···S1i	0.86	2.54	3.354 (3)	161
N2—H2A···S1ii	0.85	2.53	3.368 (3)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯S1i	0.86	2.54	3.354 (3)	161
N2—H2A⋯S1ii	0.85	2.53	3.368 (3)	168

Symmetry codes: (i) ; (ii) .