4-Chloro-benzothio-amide.

In the title compound, C(7)H(6)ClNS, the dihedral angle between the aromatic ring and the thio-amide fragment is 28.1 (2)°. The structure features a π-stacking inter-action between the aromatic rings with a slight offset of the rings, giving a centroid-centroid separation of 3.7942 (2) Å. There are inter-molecular hydrogen-bonding inter-actions between the amino group and the S atoms.

Related literature

For the uses of thio­amides, see: Akhtar et al. (2006 ▶, 2007 ▶, 2008 ▶); Jagodzinski (2003 ▶); Lebana et al. (2008 ▶). For the biological activity of thio­amides, see: Wei et al. (2006 ▶). For the synthesis of thio­amides, see: Bauer & Kuhlein (1985 ▶); Cava & Levinson (1985 ▶); Manaka & Sato (2005 ▶). For a comparable structure, see: Jian et al. (2006 ▶).

Experimental

Crystal data

C7H6ClNS

M = 171.64

Monoclinic,

a = 8.1592 (4) Å

b = 9.0934 (5) Å

c = 10.8915 (6) Å

β = 100.113 (10°

V = 795.54 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.66 mm−1

T = 296 K

0.40 × 0.36 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.778, T max = 0.889

6337 measured reflections

1901 independent reflections

1667 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.105

S = 1.06

1901 reflections

91 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.38 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/S1600536809014640/bt2933sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014640/bt2933Isup2.hkl

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

C7H6ClNS	F(000) = 352
Mr = 171.64	Dx = 1.433 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3894 reflections
a = 8.1592 (4) Å	θ = 2.5–28.5°
b = 9.0934 (5) Å	µ = 0.66 mm−1
c = 10.8915 (6) Å	T = 296 K
β = 100.113 (1)°	Block, yellow
V = 795.54 (7) Å3	0.40 × 0.36 × 0.18 mm
Z = 4

Bruker APEXII CCD diffractometer	1901 independent reflections
Radiation source: fine-focus sealed tube	1667 reflections with I > 2σ(I)
graphite	Rint = 0.017
φ and ω scans	θmax = 28.5°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→10
Tmin = 0.778, Tmax = 0.889	k = −12→12
6337 measured reflections	l = −9→14

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0539P)2 + 0.2817P] where P = (Fo2 + 2Fc2)/3
1901 reflections	(Δ/σ)max < 0.001
91 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.38 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	0.08443 (7)	0.15260 (5)	0.36191 (4)	0.05425 (18)
Cl1	0.41127 (8)	0.84764 (5)	0.55354 (7)	0.0767 (2)
N1	0.1431 (2)	0.16063 (15)	0.60516 (12)	0.0479 (4)
H1A	0.1776	0.2025	0.6758	0.058*
H1B	0.1046	0.0724	0.6028	0.058*
C1	0.14913 (18)	0.23175 (17)	0.50045 (13)	0.0367 (3)
C2	0.21721 (18)	0.38334 (16)	0.51285 (13)	0.0346 (3)
C7	0.16710 (19)	0.48716 (18)	0.41971 (14)	0.0402 (3)
H7A	0.0925	0.4603	0.3485	0.048*
C5	0.3367 (2)	0.66844 (17)	0.53788 (18)	0.0466 (4)
C6	0.2270 (2)	0.62963 (18)	0.43192 (17)	0.0462 (4)
H6A	0.1937	0.6984	0.3693	0.055*
C3	0.3294 (2)	0.42569 (19)	0.61821 (15)	0.0448 (4)
H3A	0.3647	0.3573	0.6808	0.054*
C4	0.3893 (2)	0.5685 (2)	0.63118 (17)	0.0515 (4)
H4A	0.4641	0.5963	0.7020	0.062*

	U11	U22	U33	U12	U13	U23
S1	0.0851 (4)	0.0495 (3)	0.0281 (2)	−0.0239 (2)	0.0096 (2)	−0.00374 (15)
Cl1	0.0841 (4)	0.0399 (3)	0.1008 (5)	−0.0176 (2)	0.0012 (3)	−0.0009 (2)
N1	0.0790 (10)	0.0363 (7)	0.0299 (7)	−0.0104 (6)	0.0134 (6)	−0.0014 (5)
C1	0.0449 (7)	0.0369 (7)	0.0291 (7)	−0.0020 (6)	0.0091 (6)	−0.0005 (5)
C2	0.0393 (7)	0.0345 (7)	0.0307 (7)	−0.0002 (5)	0.0085 (5)	−0.0002 (5)
C7	0.0438 (7)	0.0415 (8)	0.0341 (8)	0.0001 (6)	0.0030 (6)	0.0029 (6)
C5	0.0457 (8)	0.0337 (7)	0.0604 (11)	−0.0048 (6)	0.0095 (7)	−0.0024 (7)
C6	0.0489 (8)	0.0383 (8)	0.0504 (10)	0.0020 (7)	0.0056 (7)	0.0095 (7)
C3	0.0520 (9)	0.0422 (8)	0.0374 (8)	−0.0029 (7)	−0.0002 (6)	0.0040 (6)
C4	0.0539 (9)	0.0483 (9)	0.0477 (10)	−0.0087 (7)	−0.0036 (7)	−0.0042 (7)

S1—C1	1.6714 (15)	C7—C6	1.383 (2)
Cl1—C5	1.7374 (16)	C7—H7A	0.9300
N1—C1	1.3195 (19)	C5—C4	1.375 (3)
N1—H1A	0.8600	C5—C6	1.376 (3)
N1—H1B	0.8600	C6—H6A	0.9300
C1—C2	1.483 (2)	C3—C4	1.386 (2)
C2—C3	1.391 (2)	C3—H3A	0.9300
C2—C7	1.393 (2)	C4—H4A	0.9300
C1—N1—H1A	120.0	C4—C5—C6	121.55 (15)
C1—N1—H1B	120.0	C4—C5—Cl1	119.26 (14)
H1A—N1—H1B	120.0	C6—C5—Cl1	119.19 (14)
N1—C1—C2	116.55 (13)	C5—C6—C7	119.19 (15)
N1—C1—S1	121.02 (12)	C5—C6—H6A	120.4
C2—C1—S1	122.42 (11)	C7—C6—H6A	120.4
C3—C2—C7	118.65 (14)	C4—C3—C2	120.85 (15)
C3—C2—C1	120.94 (14)	C4—C3—H3A	119.6
C7—C2—C1	120.40 (13)	C2—C3—H3A	119.6
C6—C7—C2	120.74 (15)	C5—C4—C3	119.02 (15)
C6—C7—H7A	119.6	C5—C4—H4A	120.5
C2—C7—H7A	119.6	C3—C4—H4A	120.5
S1—C1—C2—C7	28.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···S1i	0.86	2.64	3.3769 (15)	145
N1—H1B···S1ii	0.86	2.63	3.4527 (15)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯S1i	0.86	2.64	3.3769 (15)	145
N1—H1B⋯S1ii	0.86	2.63	3.4527 (15)	160

Symmetry codes: (i) ; (ii) .