N-[(Methyl-sulfan-yl)meth-yl]benzamide.

In the title compound, C(9)H(11)NOS, the phenyl ring and formamide unit make a dihedral angle of 23.93 (14)°, whereas the (methyl-sulfan-yl)methyl group is oriented at a dihedral angle of 61.31 (8)° with respect to the phenyl ring. There are inter-molecular N-H⋯O hydrogen bonds, forming C(4) chains along the [010] direction. These polymeric chains are linked by C-H⋯O hydrogen bonds to form polymeric sheets in the (110) plane.

Related literature

For crystal structures containing the 1-(methyl­sulfan­yl)methanamine grouping, see: Siddiqui et al. (2008 ▶); Noroozi Pesyan et al. (2009 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C9H11NOS

M = 181.25

Orthorhombic,

a = 9.7841 (4) Å

b = 9.2116 (4) Å

c = 21.2663 (8) Å

V = 1916.67 (14) Å3

Z = 8

Mo Kα radiation

μ = 0.29 mm−1

T = 296 K

0.26 × 0.20 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.932, T max = 0.950

9379 measured reflections

2371 independent reflections

1722 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.116

S = 1.07

2371 reflections

110 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812004515/wn2467sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812004515/wn2467Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812004515/wn2467Isup3.cml

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

C9H11NOS	F(000) = 768
Mr = 181.25	Dx = 1.256 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1722 reflections
a = 9.7841 (4) Å	θ = 1.9–28.3°
b = 9.2116 (4) Å	µ = 0.29 mm−1
c = 21.2663 (8) Å	T = 296 K
V = 1916.67 (14) Å3	Prism, colorless
Z = 8	0.26 × 0.20 × 0.18 mm

Bruker Kappa APEXII CCD diffractometer	2371 independent reflections
Radiation source: fine-focus sealed tube	1722 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 7.50 pixels mm-1	θmax = 28.3°, θmin = 1.9°
ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −12→12
Tmin = 0.932, Tmax = 0.950	l = −27→28
9379 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0531P)2 + 0.2845P] where P = (Fo2 + 2Fc2)/3
2371 reflections	(Δ/σ)max < 0.001
110 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.20155 (6)	0.43391 (6)	−0.09248 (2)	0.0717 (2)
O1	0.14747 (12)	0.17375 (11)	0.05060 (5)	0.0537 (4)
N1	0.25653 (14)	0.38548 (15)	0.03218 (5)	0.0493 (4)
C1	0.15800 (14)	0.34302 (14)	0.13470 (7)	0.0427 (4)
C2	0.04865 (18)	0.28086 (18)	0.16623 (8)	0.0562 (5)
C3	0.0203 (2)	0.3207 (2)	0.22745 (9)	0.0710 (7)
C4	0.1003 (2)	0.4214 (2)	0.25775 (9)	0.0709 (7)
C5	0.2082 (2)	0.4838 (2)	0.22691 (8)	0.0648 (6)
C6	0.23778 (18)	0.44502 (17)	0.16551 (7)	0.0525 (5)
C7	0.18659 (14)	0.29393 (15)	0.06896 (7)	0.0424 (4)
C8	0.29981 (18)	0.3490 (2)	−0.03071 (7)	0.0559 (6)
C9	0.0467 (2)	0.3318 (3)	−0.08796 (11)	0.0905 (9)
H1	0.27659	0.46996	0.04670	0.0592*
H2	−0.00569	0.21226	0.14612	0.0674*
H3	−0.05341	0.27902	0.24832	0.0852*
H4	0.08116	0.44708	0.29912	0.0851*
H5	0.26188	0.55253	0.24731	0.0778*
H6	0.31140	0.48753	0.14487	0.0630*
H8A	0.29434	0.24449	−0.03582	0.0670*
H8B	0.39487	0.37666	−0.03557	0.0670*
H9A	0.00311	0.34980	−0.04829	0.1358*
H9B	0.06706	0.23019	−0.09169	0.1358*
H9C	−0.01321	0.36045	−0.12147	0.1358*

	U11	U22	U33	U12	U13	U23
S1	0.0957 (4)	0.0699 (4)	0.0496 (3)	−0.0010 (3)	−0.0003 (2)	0.0110 (2)
O1	0.0662 (7)	0.0395 (6)	0.0553 (6)	−0.0005 (5)	−0.0022 (5)	−0.0059 (5)
N1	0.0605 (8)	0.0426 (7)	0.0448 (7)	−0.0021 (6)	0.0027 (6)	−0.0046 (5)
C1	0.0465 (8)	0.0375 (7)	0.0440 (7)	0.0072 (6)	−0.0033 (6)	0.0001 (6)
C2	0.0588 (10)	0.0498 (9)	0.0600 (9)	−0.0024 (7)	0.0056 (8)	−0.0074 (7)
C3	0.0765 (13)	0.0686 (11)	0.0679 (12)	−0.0042 (10)	0.0239 (9)	−0.0067 (9)
C4	0.0883 (14)	0.0736 (12)	0.0509 (10)	0.0057 (11)	0.0117 (9)	−0.0129 (9)
C5	0.0733 (12)	0.0685 (11)	0.0526 (10)	−0.0033 (9)	−0.0067 (8)	−0.0134 (9)
C6	0.0541 (9)	0.0566 (9)	0.0468 (8)	−0.0028 (7)	−0.0045 (7)	−0.0024 (7)
C7	0.0445 (8)	0.0372 (7)	0.0454 (8)	0.0059 (6)	−0.0057 (6)	−0.0001 (6)
C8	0.0568 (10)	0.0632 (10)	0.0476 (9)	0.0011 (8)	0.0064 (7)	−0.0031 (8)
C9	0.0826 (15)	0.0997 (17)	0.0893 (15)	0.0017 (13)	−0.0291 (12)	0.0092 (12)

S1—C8	1.8060 (17)	C5—C6	1.384 (2)
S1—C9	1.786 (2)	C2—H2	0.9300
O1—C7	1.2347 (17)	C3—H3	0.9300
N1—C7	1.3384 (19)	C4—H4	0.9300
N1—C8	1.4426 (19)	C5—H5	0.9300
N1—H1	0.8600	C6—H6	0.9300
C1—C6	1.386 (2)	C8—H8A	0.9700
C1—C7	1.496 (2)	C8—H8B	0.9700
C1—C2	1.386 (2)	C9—H9A	0.9600
C2—C3	1.381 (3)	C9—H9B	0.9600
C3—C4	1.374 (3)	C9—H9C	0.9600
C4—C5	1.369 (3)
C8—S1—C9	100.62 (10)	C4—C3—H3	120.00
C7—N1—C8	123.03 (14)	C3—C4—H4	120.00
C8—N1—H1	118.00	C5—C4—H4	120.00
C7—N1—H1	118.00	C4—C5—H5	120.00
C2—C1—C7	118.13 (13)	C6—C5—H5	120.00
C2—C1—C6	119.07 (14)	C1—C6—H6	120.00
C6—C1—C7	122.78 (13)	C5—C6—H6	120.00
C1—C2—C3	120.08 (16)	S1—C8—H8A	109.00
C2—C3—C4	120.47 (18)	S1—C8—H8B	109.00
C3—C4—C5	119.86 (18)	N1—C8—H8A	109.00
C4—C5—C6	120.31 (17)	N1—C8—H8B	109.00
C1—C6—C5	120.20 (16)	H8A—C8—H8B	108.00
O1—C7—N1	122.59 (14)	S1—C9—H9A	109.00
O1—C7—C1	120.58 (13)	S1—C9—H9B	109.00
N1—C7—C1	116.83 (12)	S1—C9—H9C	109.00
S1—C8—N1	114.66 (12)	H9A—C9—H9B	109.00
C1—C2—H2	120.00	H9A—C9—H9C	109.00
C3—C2—H2	120.00	H9B—C9—H9C	109.00
C2—C3—H3	120.00
C9—S1—C8—N1	−73.54 (15)	C2—C1—C7—O1	−23.5 (2)
C8—N1—C7—O1	−3.9 (2)	C2—C1—C7—N1	157.05 (14)
C8—N1—C7—C1	175.55 (13)	C6—C1—C7—O1	155.07 (15)
C7—N1—C8—S1	105.09 (16)	C6—C1—C7—N1	−24.4 (2)
C6—C1—C2—C3	0.0 (2)	C1—C2—C3—C4	−0.4 (3)
C7—C1—C2—C3	178.63 (15)	C2—C3—C4—C5	0.6 (3)
C2—C1—C6—C5	0.0 (2)	C3—C4—C5—C6	−0.5 (3)
C7—C1—C6—C5	−178.51 (15)	C4—C5—C6—C1	0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.02	2.8438 (17)	160
C8—H8B···O1ii	0.97	2.53	3.434 (2)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.02	2.8438 (17)	160
C8—H8B⋯O1ii	0.97	2.53	3.434 (2)	154

Symmetry codes: (i) ; (ii) .