2-(Methyl-sulfin-yl)benzamide.

In the crystal of the title compound, C(8)H(9)NO(2)S, synthesized by the oxidation of 2-(methyl-sulfan-yl)benzamide using NaOCl with 2,2,6,6-tetra-methyl-piperidyl-1-oxy (TEMPO) as the catalyst, mol-ecules are linked via inter-molecular N-H⋯O(amide) hydrogen bonds, forming centrosymmetric amide-amide dimers which are extended into a two-dimensional lamellar framework parallel to (100) through amide-sulfinyl N-H⋯O hydrogen bonds. The benzene ring forms a dihedral angle of 25.6 (2)° with the amide group.

Related literature

For general background to sulfoxides, see: Hernández-Torres et al. (2008 ▶); Padmanabhan et al. (2000 ▶); Nieves & Lang (2002 ▶); Wedel et al. (2008 ▶); Melzig et al. (2009 ▶); Huang et al. (2006 ▶, 2010 ▶). For selective oxidation of sulfides to sulfoxides, see: Huang et al. (2006 ▶); Karimi et al. (2005 ▶); Kirihara et al. (2009 ▶); Ruff et al. (2009 ▶). For related structures, see: Kobayashi et al. (2003 ▶).

Experimental

Crystal data

C8H9NO2S

M = 183.22

Monoclinic,

a = 11.8497 (5) Å

b = 5.0376 (2) Å

c = 14.8598 (6) Å

β = 104.856 (4)°

V = 857.39 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 293 K

0.46 × 0.26 × 0.23 mm

Data collection

Oxford Diffraction Gemini Ultra CCD-detector diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.901, T max = 0.926

3438 measured reflections

1564 independent reflections

1354 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.083

S = 1.05

1564 reflections

111 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810046660/zs2076sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046660/zs2076Isup2.hkl

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

C8H9NO2S	F(000) = 384
Mr = 183.22	Dx = 1.419 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2076 reflections
a = 11.8497 (5) Å	θ = 2.8–29.3°
b = 5.0376 (2) Å	µ = 0.33 mm−1
c = 14.8598 (6) Å	T = 293 K
β = 104.856 (4)°	Block, colorless
V = 857.39 (6) Å3	0.46 × 0.26 × 0.23 mm
Z = 4

Oxford Diffraction Gemini Ultra CCD-detector diffractometer	1564 independent reflections
Radiation source: fine-focus sealed tube	1354 reflections with I > 2σ(I)
graphite	Rint = 0.019
Detector resolution: 10.3592 pixels mm-1	θmax = 25.3°, θmin = 2.8°
ω scans	h = −14→14
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −4→6
Tmin = 0.901, Tmax = 0.926	l = −14→17
3438 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030	H-atom parameters constrained
wR(F2) = 0.083	w = 1/[σ2(Fo2) + (0.0391P)2 + 0.2897P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
1564 reflections	Δρmax = 0.25 e Å−3
111 parameters	Δρmin = −0.22 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.042 (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	0.70440 (4)	0.05668 (9)	0.75213 (3)	0.03131 (18)
O1	0.78768 (11)	−0.0190 (3)	0.84272 (9)	0.0493 (4)
O2	0.56496 (11)	0.2416 (3)	0.58587 (9)	0.0443 (4)
N1	0.64197 (13)	0.4202 (3)	0.47654 (10)	0.0415 (4)
H1A	0.5843	0.5281	0.4588	0.050*
H1B	0.6982	0.4221	0.4497	0.050*
C1	0.77553 (14)	−0.0412 (3)	0.66326 (12)	0.0292 (4)
C2	0.86744 (15)	−0.2174 (4)	0.68979 (13)	0.0400 (5)
H2	0.8878	−0.2850	0.7500	0.048*
C3	0.92910 (16)	−0.2930 (4)	0.62648 (14)	0.0463 (5)
H3	0.9904	−0.4132	0.6440	0.056*
C4	0.89971 (16)	−0.1907 (4)	0.53778 (14)	0.0449 (5)
H4	0.9409	−0.2428	0.4952	0.054*
C5	0.80940 (16)	−0.0109 (4)	0.51166 (13)	0.0393 (5)
H5	0.7911	0.0593	0.4518	0.047*
C6	0.74535 (14)	0.0670 (3)	0.57362 (11)	0.0297 (4)
C7	0.59562 (16)	−0.1977 (4)	0.73172 (14)	0.0418 (5)
H7A	0.5457	−0.1791	0.6700	0.063*
H7C	0.5500	−0.1821	0.7763	0.063*
H7B	0.6328	−0.3685	0.7379	0.063*
C8	0.64414 (14)	0.2510 (4)	0.54531 (11)	0.0326 (4)

	U11	U22	U33	U12	U13	U23
S1	0.0344 (3)	0.0335 (3)	0.0278 (3)	0.00090 (18)	0.01129 (18)	−0.00260 (18)
O1	0.0443 (8)	0.0777 (11)	0.0256 (7)	0.0052 (7)	0.0086 (6)	−0.0005 (7)
O2	0.0423 (7)	0.0527 (8)	0.0439 (8)	0.0163 (6)	0.0220 (6)	0.0167 (7)
N1	0.0389 (9)	0.0496 (10)	0.0386 (9)	0.0102 (8)	0.0147 (7)	0.0159 (8)
C1	0.0279 (8)	0.0322 (9)	0.0280 (9)	−0.0001 (7)	0.0084 (7)	−0.0029 (7)
C2	0.0363 (10)	0.0476 (12)	0.0350 (10)	0.0094 (9)	0.0069 (8)	0.0010 (9)
C3	0.0362 (10)	0.0525 (13)	0.0506 (12)	0.0148 (9)	0.0118 (9)	−0.0032 (10)
C4	0.0399 (10)	0.0554 (13)	0.0455 (12)	0.0041 (10)	0.0221 (9)	−0.0085 (10)
C5	0.0440 (10)	0.0466 (11)	0.0310 (10)	0.0022 (9)	0.0162 (8)	−0.0005 (8)
C6	0.0300 (9)	0.0317 (9)	0.0282 (9)	−0.0017 (7)	0.0088 (7)	−0.0019 (7)
C7	0.0428 (10)	0.0370 (11)	0.0498 (11)	−0.0030 (9)	0.0195 (9)	0.0003 (9)
C8	0.0350 (9)	0.0359 (10)	0.0269 (9)	0.0009 (8)	0.0080 (7)	−0.0009 (8)

S1—O1	1.5000 (13)	C3—C4	1.374 (3)
S1—C7	1.7875 (19)	C3—H3	0.9300
S1—C1	1.8078 (17)	C4—C5	1.380 (3)
O2—C8	1.239 (2)	C4—H4	0.9300
N1—C8	1.326 (2)	C5—C6	1.391 (2)
N1—H1A	0.8600	C5—H5	0.9300
N1—H1B	0.8600	C6—C8	1.488 (2)
C1—C2	1.382 (3)	C7—H7A	0.9600
C1—C6	1.398 (2)	C7—H7C	0.9600
C2—C3	1.384 (3)	C7—H7B	0.9600
C2—H2	0.9300
O1—S1—C7	104.47 (9)	C5—C4—H4	119.9
O1—S1—C1	105.28 (8)	C4—C5—C6	120.95 (17)
C7—S1—C1	97.56 (8)	C4—C5—H5	119.5
C8—N1—H1A	120.0	C6—C5—H5	119.5
C8—N1—H1B	120.0	C5—C6—C1	118.09 (16)
H1A—N1—H1B	120.0	C5—C6—C8	121.68 (15)
C2—C1—C6	120.83 (16)	C1—C6—C8	120.18 (15)
C2—C1—S1	116.60 (13)	S1—C7—H7A	109.5
C6—C1—S1	122.44 (13)	S1—C7—H7C	109.5
C1—C2—C3	119.85 (17)	H7A—C7—H7C	109.5
C1—C2—H2	120.1	S1—C7—H7B	109.5
C3—C2—H2	120.1	H7A—C7—H7B	109.5
C4—C3—C2	120.01 (18)	H7C—C7—H7B	109.5
C4—C3—H3	120.0	O2—C8—N1	122.13 (16)
C2—C3—H3	120.0	O2—C8—C6	119.62 (15)
C3—C4—C5	120.24 (17)	N1—C8—C6	118.24 (15)
C3—C4—H4	119.9

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.86	2.08	2.934 (2)	175
N1—H1B···O1ii	0.86	2.18	2.991 (2)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.86	2.08	2.934 (2)	175
N1—H1B⋯O1ii	0.86	2.18	2.991 (2)	157

Symmetry codes: (i) ; (ii) .