3-Methyl-thio-benzamide.

In the title compound, C(8)H(9)NS, the dihedral angle between the aromatic ring and the thio-amide fragment is 36.0 (2)°. There are π-stacking inter-actions between coplanar aryl fragments, with a centroid-centroid separation of 3.658 (2) Å. In addition, there are inter-molecular hydrogen bonds between the amino group and the S atoms.

Related literature

For our previous work on the synthesis and biological screening of five-membered heterocycles, see: Akhtar et al. (2006 ▶, 2007 ▶, 2008 ▶); Serwar et al. (2009 ▶). For related structures, see: Jian et al. (2006 ▶); Khan et al. (2009a ▶,b ▶).

Experimental

Crystal data

C8H9NS

M = 151.22

Monoclinic,

a = 7.717 (5) Å

b = 10.267 (7) Å

c = 10.100 (7) Å

β = 97.186 (9)°

V = 794.0 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 296 K

0.37 × 0.27 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.793, T max = 0.930

6234 measured reflections

1797 independent reflections

1447 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.112

S = 1.08

1797 reflections

92 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.29 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/S1600536809019849/bt2967sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019849/bt2967Isup2.hkl

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

C8H9NS	F(000) = 320
Mr = 151.22	Dx = 1.265 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2572 reflections
a = 7.717 (5) Å	θ = 2.7–27.1°
b = 10.267 (7) Å	µ = 0.33 mm−1
c = 10.100 (7) Å	T = 296 K
β = 97.186 (9)°	Block, yellow
V = 794.0 (9) Å3	0.37 × 0.27 × 0.20 mm
Z = 4

Bruker APEXII CCD diffractometer	1797 independent reflections
Radiation source: fine-focus sealed tube	1447 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→9
Tmin = 0.793, Tmax = 0.930	k = −13→13
6234 measured reflections	l = −11→13

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0556P)2 + 0.242P] where P = (Fo2 + 2Fc2)/3
1797 reflections	(Δ/σ)max < 0.001
92 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.29 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	0.13324 (7)	0.62675 (4)	0.16035 (4)	0.05023 (19)
N1	0.0243 (2)	0.38549 (15)	0.17149 (16)	0.0521 (4)
H1A	0.0187	0.3113	0.2103	0.063*
H1B	−0.0260	0.3963	0.0914	0.063*
C2	0.1933 (2)	0.45618 (15)	0.37261 (16)	0.0358 (4)
C1	0.1099 (2)	0.48241 (16)	0.23470 (16)	0.0379 (4)
C3	0.2661 (2)	0.33439 (17)	0.40481 (18)	0.0406 (4)
H3A	0.2535	0.2683	0.3414	0.049*
C7	0.2072 (2)	0.55347 (17)	0.46931 (18)	0.0435 (4)
H7A	0.1589	0.6352	0.4492	0.052*
C4	0.3569 (2)	0.30980 (18)	0.52939 (19)	0.0455 (4)
C5	0.3695 (2)	0.4084 (2)	0.62387 (18)	0.0500 (5)
H5A	0.4303	0.3935	0.7079	0.060*
C6	0.2927 (3)	0.5286 (2)	0.59491 (19)	0.0501 (5)
H6A	0.2989	0.5927	0.6604	0.060*
C8	0.4466 (3)	0.1803 (2)	0.5575 (2)	0.0671 (6)
H8A	0.3710	0.1115	0.5210	0.101*
H8B	0.4729	0.1686	0.6522	0.101*
H8C	0.5529	0.1786	0.5173	0.101*

	U11	U22	U33	U12	U13	U23
S1	0.0774 (4)	0.0330 (2)	0.0387 (3)	0.0000 (2)	0.0007 (2)	0.00264 (17)
N1	0.0726 (11)	0.0435 (8)	0.0363 (8)	−0.0142 (7)	−0.0089 (7)	0.0048 (6)
C2	0.0384 (8)	0.0362 (8)	0.0329 (8)	−0.0031 (6)	0.0046 (6)	0.0001 (6)
C1	0.0439 (9)	0.0345 (8)	0.0351 (9)	0.0016 (6)	0.0042 (7)	−0.0013 (6)
C3	0.0461 (9)	0.0380 (8)	0.0379 (9)	−0.0003 (7)	0.0066 (7)	0.0007 (7)
C7	0.0508 (10)	0.0396 (9)	0.0398 (9)	−0.0018 (7)	0.0045 (8)	−0.0032 (7)
C4	0.0433 (9)	0.0492 (10)	0.0446 (10)	0.0012 (7)	0.0078 (7)	0.0129 (8)
C5	0.0482 (10)	0.0674 (12)	0.0332 (9)	−0.0082 (9)	−0.0003 (8)	0.0076 (8)
C6	0.0576 (11)	0.0554 (11)	0.0369 (10)	−0.0097 (9)	0.0040 (8)	−0.0083 (8)
C8	0.0737 (14)	0.0647 (14)	0.0630 (14)	0.0205 (11)	0.0093 (11)	0.0223 (11)

S1—C1	1.6811 (19)	C7—H7A	0.9300
N1—C1	1.315 (2)	C4—C5	1.386 (3)
N1—H1A	0.8600	C4—C8	1.509 (3)
N1—H1B	0.8600	C5—C6	1.384 (3)
C2—C7	1.392 (2)	C5—H5A	0.9300
C2—C3	1.393 (2)	C6—H6A	0.9300
C2—C1	1.484 (2)	C8—H8A	0.9600
C3—C4	1.385 (3)	C8—H8B	0.9600
C3—H3A	0.9300	C8—H8C	0.9600
C7—C6	1.379 (3)
C1—N1—H1A	120.0	C3—C4—C5	118.45 (17)
C1—N1—H1B	120.0	C3—C4—C8	119.99 (18)
H1A—N1—H1B	120.0	C5—C4—C8	121.49 (19)
C7—C2—C3	119.16 (16)	C6—C5—C4	120.95 (18)
C7—C2—C1	120.98 (15)	C6—C5—H5A	119.5
C3—C2—C1	119.80 (15)	C4—C5—H5A	119.5
N1—C1—C2	116.80 (15)	C7—C6—C5	120.17 (17)
N1—C1—S1	121.71 (14)	C7—C6—H6A	119.9
C2—C1—S1	121.41 (12)	C5—C6—H6A	119.9
C4—C3—C2	121.29 (17)	C4—C8—H8A	109.5
C4—C3—H3A	119.4	C4—C8—H8B	109.5
C2—C3—H3A	119.4	H8A—C8—H8B	109.5
C6—C7—C2	119.91 (17)	C4—C8—H8C	109.5
C6—C7—H7A	120.0	H8A—C8—H8C	109.5
C2—C7—H7A	120.0	H8B—C8—H8C	109.5
N1—C1—C2—C3	36.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···S1i	0.86	2.66	3.455 (2)	155
N1—H1B···S1ii	0.86	2.58	3.422 (3)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯S1i	0.86	2.66	3.455 (2)	155
N1—H1B⋯S1ii	0.86	2.58	3.422 (3)	165

Symmetry codes: (i) ; (ii) .