4-Methyl-benzene-carbothio-amide.

In the title mol-ecule, C(8)H(9)NS, the mean plane of the carbothio-amide group is twisted slightly with respect to the mean plane of the benzene ring, making a dihedral angle of 17.03 (10)°. The crystal structure is stabilized by inter-molecular N-H⋯S hydrogen bonds, resulting in the formation of eight-membered rings lying about inversion centers and representing R(2) (2)(8) and R(4) (2)(8) motifs. Futhermore, these hydrogen bonds build up chains parallel to the b axis.

Related literature

For the use of thio­amides as inter­mediates in the synthesis of various heterocyclic compounds, see: Zahid et al. (2009 ▶). For the uses of thio­amides, see: Lebana et al. (2008 ▶). For the biological activity of thio­amides, see: Jagodzinski (2003 ▶); Klimesova et al. (1999 ▶). For related structures, see: Khan et al. (2009a ▶,b ▶,c ▶); Jian et al. (2006 ▶); Ali et al. (2010 ▶). For graph-set notation, see: Etter et al. (1990 ▶); Bernstein et al. (1994 ▶).

Experimental

Crystal data

C8H9NS

M = 151.22

Monoclinic,

a = 9.7341 (5) Å

b = 5.8391 (2) Å

c = 13.9055 (6) Å

β = 104.946 (3)°

V = 763.63 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 123 K

0.10 × 0.06 × 0.06 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.967, T max = 0.980

2741 measured reflections

1482 independent reflections

1399 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.089

S = 1.06

1482 reflections

92 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.24 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810015813/dn2557sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015813/dn2557Isup2.hkl

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

C8H9NS	F(000) = 320
Mr = 151.22	Dx = 1.315 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1473 reflections
a = 9.7341 (5) Å	θ = 1.0–26.0°
b = 5.8391 (2) Å	µ = 0.34 mm−1
c = 13.9055 (6) Å	T = 123 K
β = 104.946 (3)°	Block, yellow
V = 763.63 (6) Å3	0.10 × 0.06 × 0.06 mm
Z = 4

Nonius KappaCCD diffractometer	1482 independent reflections
Radiation source: fine-focus sealed tube	1399 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω and φ scans	θmax = 26.0°, θmin = 3.8°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −11→11
Tmin = 0.967, Tmax = 0.980	k = −7→7
2741 measured reflections	l = −16→16

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)] = 0.034	Hydrogen site location: difference Fourier map
wR(F2) = 0.089	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0373P)2 + 0.5912P] where P = (Fo2 + 2Fc2)/3
1482 reflections	(Δ/σ)max < 0.001
92 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.24 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.

	x	y	z	Uiso*/Ueq
S1	0.15464 (4)	0.79266 (7)	0.03136 (3)	0.02316 (16)
N1	0.19369 (15)	0.3538 (2)	0.06514 (10)	0.0219 (3)
H1A	0.2463	0.2313	0.0844	0.026*
H1B	0.1007	0.3410	0.0440	0.026*
C1	0.41221 (16)	0.5673 (3)	0.10461 (11)	0.0168 (3)
C2	0.48580 (17)	0.7599 (3)	0.08529 (11)	0.0189 (3)
H2	0.4344	0.8849	0.0496	0.023*
C3	0.63277 (18)	0.7714 (3)	0.11743 (12)	0.0207 (4)
H3	0.6805	0.9045	0.1037	0.025*
C4	0.71154 (17)	0.5908 (3)	0.16965 (11)	0.0203 (4)
C5	0.63795 (18)	0.3995 (3)	0.19021 (11)	0.0211 (4)
H5	0.6897	0.2753	0.2264	0.025*
C6	0.49105 (17)	0.3872 (3)	0.15894 (11)	0.0196 (3)
H6	0.4433	0.2557	0.1744	0.023*
C7	0.25443 (17)	0.5571 (3)	0.06803 (11)	0.0177 (3)
C8	0.87114 (18)	0.6011 (3)	0.20278 (13)	0.0280 (4)
H8A	0.9033	0.7532	0.1883	0.042*
H8B	0.9114	0.4848	0.1671	0.042*
H8C	0.9028	0.5719	0.2745	0.042*

	U11	U22	U33	U12	U13	U23
S1	0.0174 (2)	0.0146 (2)	0.0353 (3)	0.00051 (14)	0.00272 (18)	0.00029 (16)
N1	0.0160 (7)	0.0155 (7)	0.0332 (8)	−0.0010 (6)	0.0045 (6)	0.0019 (6)
C1	0.0192 (8)	0.0154 (8)	0.0163 (7)	−0.0005 (6)	0.0055 (6)	−0.0017 (6)
C2	0.0205 (8)	0.0156 (7)	0.0204 (7)	0.0009 (6)	0.0050 (6)	0.0019 (6)
C3	0.0215 (8)	0.0192 (8)	0.0221 (8)	−0.0032 (6)	0.0066 (6)	−0.0004 (6)
C4	0.0193 (8)	0.0229 (8)	0.0182 (7)	0.0001 (6)	0.0041 (6)	−0.0033 (6)
C5	0.0240 (8)	0.0203 (8)	0.0180 (7)	0.0042 (6)	0.0037 (6)	0.0024 (6)
C6	0.0234 (8)	0.0158 (8)	0.0202 (7)	−0.0018 (6)	0.0068 (6)	0.0009 (6)
C7	0.0204 (8)	0.0161 (8)	0.0170 (7)	−0.0007 (6)	0.0057 (6)	−0.0007 (6)
C8	0.0194 (9)	0.0328 (10)	0.0299 (9)	0.0000 (7)	0.0026 (7)	0.0007 (8)

S1—C7	1.6852 (16)	C3—H3	0.9500
N1—C7	1.322 (2)	C4—C5	1.396 (2)
N1—H1A	0.8800	C4—C8	1.503 (2)
N1—H1B	0.8800	C5—C6	1.385 (2)
C1—C2	1.396 (2)	C5—H5	0.9500
C1—C6	1.403 (2)	C6—H6	0.9500
C1—C7	1.489 (2)	C8—H8A	0.9800
C2—C3	1.386 (2)	C8—H8B	0.9800
C2—H2	0.9500	C8—H8C	0.9800
C3—C4	1.393 (2)
C7—N1—H1A	120.0	C6—C5—C4	121.35 (15)
C7—N1—H1B	120.0	C6—C5—H5	119.3
H1A—N1—H1B	120.0	C4—C5—H5	119.3
C2—C1—C6	118.11 (15)	C5—C6—C1	120.48 (15)
C2—C1—C7	120.12 (14)	C5—C6—H6	119.8
C6—C1—C7	121.77 (14)	C1—C6—H6	119.8
C3—C2—C1	121.02 (15)	N1—C7—C1	117.39 (14)
C3—C2—H2	119.5	N1—C7—S1	120.35 (12)
C1—C2—H2	119.5	C1—C7—S1	122.26 (12)
C2—C3—C4	120.99 (15)	C4—C8—H8A	109.5
C2—C3—H3	119.5	C4—C8—H8B	109.5
C4—C3—H3	119.5	H8A—C8—H8B	109.5
C3—C4—C5	118.04 (15)	C4—C8—H8C	109.5
C3—C4—C8	121.05 (15)	H8A—C8—H8C	109.5
C5—C4—C8	120.91 (15)	H8B—C8—H8C	109.5
C6—C1—C2—C3	1.0 (2)	C4—C5—C6—C1	0.6 (2)
C7—C1—C2—C3	−179.07 (14)	C2—C1—C6—C5	−1.4 (2)
C1—C2—C3—C4	0.3 (2)	C7—C1—C6—C5	178.65 (14)
C2—C3—C4—C5	−1.1 (2)	C2—C1—C7—N1	162.91 (15)
C2—C3—C4—C8	178.76 (15)	C6—C1—C7—N1	−17.2 (2)
C3—C4—C5—C6	0.7 (2)	C2—C1—C7—S1	−17.1 (2)
C8—C4—C5—C6	−179.18 (15)	C6—C1—C7—S1	162.78 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···S1i	0.88	2.56	3.4178 (14)	166
N1—H1A···S1ii	0.88	2.75	3.3179 (15)	124

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯S1i	0.88	2.56	3.4178 (14)	166
N1—H1A⋯S1ii	0.88	2.75	3.3179 (15)	124

Symmetry codes: (i) ; (ii) .