4-Bromo-thio-benzamide.

The title compound, C(7)H(6)BrNS, crystallizes with two mol-ecules in the asymmetric unit. The dihedral angles between the aromatic ring and the thio-amide fragment are 23.6 (4) and 20.5 (3)° in the two mol-ecules. In the crystal, there are inter-molecular N-H⋯S hydrogen-bonding inter-actions between the amine group and the S atoms.

Related literature

For the uses of thio­amides, see: Akhtar et al. (2006 ▶, 2007 ▶, 2008 ▶); Jagodzinski et al. (2003 ▶). For the biological activity of thio­amides, see: Wei et al. (2006 ▶); Klimesova et al. (1999 ▶). For the synthesis of thio­amides, see: Kaboudin et al. (2006 ▶); Cava et al. (1985 ▶). For related crystal structures, see: Khan et al. (2009 ▶); Jian et al. (2006 ▶); Manaka & Sato (2005 ▶).

Experimental

Crystal data

C7H6BrNS

M = 216.10

Monoclinic,

a = 19.6325 (11) Å

b = 10.6101 (6) Å

c = 7.8859 (5) Å

β = 100.078 (1)°

V = 1617.31 (16) Å3

Z = 8

Mo Kα radiation

μ = 5.26 mm−1

T = 296 K

0.21 × 0.17 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.384, T max = 0.620

12968 measured reflections

3911 independent reflections

2706 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.087

S = 1.03

3911 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.82 e Å−3

Δρmin = −0.78 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809018273/bt2956sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018273/bt2956Isup2.hkl

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

C7H6BrNS	F(000) = 848
Mr = 216.10	Dx = 1.775 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3900 reflections
a = 19.6325 (11) Å	θ = 2.2–26.9°
b = 10.6101 (6) Å	µ = 5.26 mm−1
c = 7.8859 (5) Å	T = 296 K
β = 100.078 (1)°	Block, yellow
V = 1617.31 (16) Å3	0.21 × 0.17 × 0.09 mm
Z = 8

Bruker APEXII CCD diffractometer	3911 independent reflections
Radiation source: fine-focus sealed tube	2706 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −25→25
Tmin = 0.384, Tmax = 0.620	k = −13→14
12968 measured reflections	l = −10→10

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0372P)2 + 0.7786P] where P = (Fo2 + 2Fc2)/3
3911 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 0.82 e Å−3
0 restraints	Δρmin = −0.77 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
Br2	0.315314 (16)	0.36346 (4)	0.36641 (5)	0.07035 (13)
Br1	0.538072 (18)	0.69050 (5)	1.27120 (5)	0.08477 (16)
S2	−0.04123 (4)	0.26135 (7)	0.39188 (10)	0.05003 (18)
S1	0.21328 (4)	0.52885 (7)	0.75427 (10)	0.05230 (19)
N2	−0.03383 (11)	0.4881 (2)	0.2688 (3)	0.0473 (6)
H2A	−0.0119	0.5515	0.2367	0.057*
H2B	−0.0780	0.4916	0.2623	0.057*
C1	0.23831 (13)	0.6495 (2)	0.8875 (3)	0.0412 (6)
C9	0.07643 (12)	0.3842 (2)	0.3369 (3)	0.0342 (5)
C12	0.21855 (13)	0.3743 (3)	0.3549 (3)	0.0429 (6)
C10	0.10919 (14)	0.4633 (2)	0.2364 (4)	0.0459 (6)
H10A	0.0831	0.5200	0.1618	0.055*
C14	0.11668 (14)	0.3004 (3)	0.4448 (3)	0.0474 (7)
H14A	0.0956	0.2466	0.5131	0.057*
C5	0.44606 (15)	0.6804 (3)	1.1491 (4)	0.0558 (8)
C8	0.00020 (13)	0.3859 (2)	0.3280 (3)	0.0370 (5)
C13	0.18748 (14)	0.2945 (3)	0.4535 (4)	0.0515 (7)
H13A	0.2137	0.2366	0.5260	0.062*
C11	0.18020 (15)	0.4589 (3)	0.2457 (4)	0.0498 (7)
H11A	0.2018	0.5127	0.1785	0.060*
N1	0.19425 (12)	0.7375 (2)	0.9174 (3)	0.0554 (6)
H1A	0.2082	0.7985	0.9867	0.067*
H1B	0.1517	0.7338	0.8675	0.067*
C2	0.31088 (13)	0.6623 (2)	0.9781 (3)	0.0408 (6)
C6	0.40650 (16)	0.7873 (3)	1.1197 (4)	0.0622 (8)
H6A	0.4250	0.8654	1.1563	0.075*
C3	0.35274 (15)	0.5562 (3)	1.0060 (4)	0.0549 (7)
H3A	0.3351	0.4783	0.9659	0.066*
C7	0.33903 (15)	0.7780 (3)	1.0352 (4)	0.0540 (7)
H7A	0.3119	0.8502	1.0162	0.065*
C4	0.42000 (16)	0.5644 (3)	1.0919 (4)	0.0639 (9)
H4A	0.4475	0.4926	1.1110	0.077*

	U11	U22	U33	U12	U13	U23
Br2	0.03962 (17)	0.0895 (3)	0.0834 (3)	0.00005 (15)	0.01476 (15)	0.00159 (19)
Br1	0.04511 (19)	0.1196 (4)	0.0842 (3)	−0.00878 (19)	−0.00386 (16)	−0.0108 (2)
S2	0.0434 (4)	0.0390 (4)	0.0685 (5)	−0.0063 (3)	0.0120 (3)	0.0056 (3)
S1	0.0465 (4)	0.0459 (4)	0.0626 (5)	−0.0022 (3)	0.0043 (3)	−0.0081 (3)
N2	0.0398 (12)	0.0358 (12)	0.0667 (15)	0.0016 (9)	0.0101 (11)	0.0030 (11)
C1	0.0427 (14)	0.0402 (14)	0.0415 (14)	0.0002 (11)	0.0096 (11)	0.0055 (11)
C9	0.0400 (13)	0.0271 (12)	0.0358 (13)	−0.0022 (10)	0.0076 (10)	−0.0035 (10)
C12	0.0405 (14)	0.0435 (15)	0.0448 (15)	−0.0022 (12)	0.0078 (11)	−0.0071 (12)
C10	0.0485 (15)	0.0347 (14)	0.0566 (17)	0.0078 (12)	0.0150 (12)	0.0086 (12)
C14	0.0444 (15)	0.0515 (17)	0.0459 (15)	−0.0021 (12)	0.0067 (12)	0.0152 (13)
C5	0.0392 (15)	0.078 (2)	0.0497 (17)	−0.0057 (15)	0.0057 (12)	−0.0030 (15)
C8	0.0428 (13)	0.0305 (13)	0.0375 (13)	−0.0018 (10)	0.0065 (10)	−0.0057 (10)
C13	0.0420 (15)	0.0607 (18)	0.0499 (16)	0.0040 (13)	0.0023 (12)	0.0138 (14)
C11	0.0552 (17)	0.0372 (15)	0.0628 (18)	−0.0003 (13)	0.0261 (14)	0.0071 (13)
N1	0.0442 (13)	0.0528 (15)	0.0659 (16)	0.0090 (11)	0.0004 (11)	−0.0115 (12)
C2	0.0395 (13)	0.0418 (15)	0.0420 (14)	0.0003 (11)	0.0099 (11)	0.0036 (11)
C6	0.0509 (18)	0.063 (2)	0.072 (2)	−0.0100 (15)	0.0088 (15)	−0.0202 (17)
C3	0.0483 (16)	0.0439 (16)	0.069 (2)	−0.0015 (13)	0.0022 (14)	0.0035 (14)
C7	0.0518 (17)	0.0471 (17)	0.0633 (19)	−0.0007 (13)	0.0108 (14)	−0.0083 (14)
C4	0.0477 (17)	0.058 (2)	0.082 (2)	0.0054 (15)	0.0008 (15)	0.0080 (17)

Br2—C12	1.890 (3)	C14—C13	1.381 (4)
Br1—C5	1.896 (3)	C14—H14A	0.9300
S2—C8	1.675 (3)	C5—C6	1.371 (5)
S1—C1	1.674 (3)	C5—C4	1.379 (5)
N2—C8	1.316 (3)	C13—H13A	0.9300
N2—H2A	0.8600	C11—H11A	0.9300
N2—H2B	0.8600	N1—H1A	0.8600
C1—N1	1.322 (3)	N1—H1B	0.8600
C1—C2	1.484 (4)	C2—C3	1.388 (4)
C9—C14	1.380 (3)	C2—C7	1.389 (4)
C9—C10	1.388 (3)	C6—C7	1.378 (4)
C9—C8	1.486 (3)	C6—H6A	0.9300
C12—C13	1.364 (4)	C3—C4	1.377 (4)
C12—C11	1.373 (4)	C3—H3A	0.9300
C10—C11	1.384 (4)	C7—H7A	0.9300
C10—H10A	0.9300	C4—H4A	0.9300
C8—N2—H2A	120.0	C12—C13—C14	119.3 (3)
C8—N2—H2B	120.0	C12—C13—H13A	120.3
H2A—N2—H2B	120.0	C14—C13—H13A	120.3
N1—C1—C2	116.9 (2)	C12—C11—C10	119.5 (3)
N1—C1—S1	121.5 (2)	C12—C11—H11A	120.3
C2—C1—S1	121.58 (19)	C10—C11—H11A	120.3
C14—C9—C10	118.0 (2)	C1—N1—H1A	120.0
C14—C9—C8	120.0 (2)	C1—N1—H1B	120.0
C10—C9—C8	122.0 (2)	H1A—N1—H1B	120.0
C13—C12—C11	120.8 (3)	C3—C2—C7	118.3 (3)
C13—C12—Br2	118.7 (2)	C3—C2—C1	119.6 (2)
C11—C12—Br2	120.4 (2)	C7—C2—C1	122.1 (2)
C11—C10—C9	120.8 (2)	C5—C6—C7	119.3 (3)
C11—C10—H10A	119.6	C5—C6—H6A	120.3
C9—C10—H10A	119.6	C7—C6—H6A	120.3
C9—C14—C13	121.5 (2)	C4—C3—C2	121.1 (3)
C9—C14—H14A	119.2	C4—C3—H3A	119.4
C13—C14—H14A	119.2	C2—C3—H3A	119.4
C6—C5—C4	121.1 (3)	C6—C7—C2	121.0 (3)
C6—C5—Br1	120.0 (2)	C6—C7—H7A	119.5
C4—C5—Br1	118.9 (2)	C2—C7—H7A	119.5
N2—C8—C9	118.1 (2)	C3—C4—C5	119.1 (3)
N2—C8—S2	120.9 (2)	C3—C4—H4A	120.5
C9—C8—S2	120.96 (18)	C5—C4—H4A	120.5
C3—C1—C2—S1	23.6 (3)	C14—C8—C9—S2	20.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···S2i	0.86	2.73	3.583 (2)	172
N2—H2B···S1ii	0.86	2.65	3.500 (2)	173
N1—H1A···S1iii	0.86	2.78	3.605 (3)	160
N1—H1B···S2ii	0.86	2.71	3.523 (2)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯S2i	0.86	2.73	3.583 (2)	172
N2—H2B⋯S1ii	0.86	2.65	3.500 (2)	173
N1—H1A⋯S1iii	0.86	2.78	3.605 (3)	160
N1—H1B⋯S2ii	0.86	2.71	3.523 (2)	158

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