N-[(4-Methyl-phen-yl)sulfon-yl]acetamide.

In the title compound, C(9)H(11)NO(3)S, the dihedral angle between the benzene ring and the amide group is 76.7 (3)°. In the crystal, mol-ecules are linked by pairs of C-H⋯O hydrogen bonds into inversion dimers with R(2) (2)(8) ring motifs. The dimers are further connected by N-H⋯O and C-H⋯O hydrogen bonds into an infinite tape running parallel to the b-axis direction.

Related literature

For details of the biological activity of sulfonamides, see: Kamoshita et al. (1987 ▶); Heidler & Link (2005 ▶); Ashton et al. (1994 ▶). For related structures, see: Henschel et al. (1996 ▶); Gowda et al. (2007 ▶, 2010 ▶); Shakuntala et al. (2011a ▶,b ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C9H11NO3S

M = 213.25

Monoclinic,

a = 9.2514 (6) Å

b = 5.1900 (3) Å

c = 20.5873 (13) Å

β = 95.070 (2)°

V = 984.63 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 100 K

0.27 × 0.19 × 0.08 mm

Data collection

Bruker APEX DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.922, T max = 0.976

15682 measured reflections

3114 independent reflections

2577 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.086

S = 1.07

3114 reflections

133 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812024658/hb6824sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812024658/hb6824Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812024658/hb6824Isup3.cml

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

C9H11NO3S	F(000) = 448
Mr = 213.25	Dx = 1.439 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5205 reflections
a = 9.2514 (6) Å	θ = 2.8–30.9°
b = 5.1900 (3) Å	µ = 0.31 mm−1
c = 20.5873 (13) Å	T = 100 K
β = 95.070 (2)°	Plate, colourless
V = 984.63 (11) Å3	0.27 × 0.19 × 0.08 mm
Z = 4

Bruker APEX DUO CCD diffractometer	3114 independent reflections
Radiation source: fine-focus sealed tube	2577 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
φ and ω scans	θmax = 31.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→13
Tmin = 0.922, Tmax = 0.976	k = −7→7
15682 measured reflections	l = −29→29

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0405P)2 + 0.3454P] where P = (Fo2 + 2Fc2)/3
3114 reflections	(Δ/σ)max < 0.001
133 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.36 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.45077 (3)	0.60012 (5)	0.397692 (13)	0.01332 (8)
O1	0.45409 (9)	0.84344 (17)	0.43094 (4)	0.01789 (18)
O2	0.58468 (9)	0.47512 (18)	0.38706 (4)	0.01848 (18)
O3	0.16276 (10)	0.63022 (17)	0.44799 (5)	0.02044 (19)
N1	0.36478 (11)	0.3887 (2)	0.44001 (5)	0.01466 (19)
C1	0.09268 (15)	0.7079 (3)	0.13904 (6)	0.0264 (3)
H1A	0.0199	0.8436	0.1421	0.040*
H1B	0.0439	0.5443	0.1277	0.040*
H1C	0.1566	0.7532	0.1053	0.040*
C2	0.18124 (13)	0.6809 (3)	0.20370 (6)	0.0186 (2)
C3	0.16453 (13)	0.8551 (2)	0.25401 (6)	0.0191 (2)
H3A	0.0962	0.9912	0.2474	0.023*
C4	0.24621 (13)	0.8331 (2)	0.31380 (6)	0.0180 (2)
H4A	0.2341	0.9525	0.3479	0.022*
C5	0.34592 (12)	0.6332 (2)	0.32277 (5)	0.0143 (2)
C6	0.36550 (13)	0.4571 (2)	0.27322 (6)	0.0179 (2)
H6A	0.4346	0.3221	0.2798	0.022*
C7	0.28242 (14)	0.4823 (3)	0.21408 (6)	0.0202 (2)
H7A	0.2946	0.3625	0.1801	0.024*
C8	0.22879 (12)	0.4332 (2)	0.46235 (5)	0.0153 (2)
C9	0.17645 (13)	0.2221 (2)	0.50349 (6)	0.0196 (2)
H9A	0.0778	0.2610	0.5143	0.029*
H9B	0.2409	0.2074	0.5437	0.029*
H9C	0.1763	0.0591	0.4795	0.029*
H1N1	0.4057 (19)	0.242 (4)	0.4444 (8)	0.029 (4)*

	U11	U22	U33	U12	U13	U23
S1	0.01197 (13)	0.01170 (13)	0.01619 (13)	0.00063 (9)	0.00059 (9)	−0.00001 (10)
O1	0.0193 (4)	0.0129 (4)	0.0210 (4)	−0.0007 (3)	−0.0014 (3)	−0.0024 (3)
O2	0.0130 (4)	0.0194 (4)	0.0232 (4)	0.0032 (3)	0.0022 (3)	0.0007 (3)
O3	0.0175 (4)	0.0155 (4)	0.0287 (5)	0.0033 (3)	0.0042 (3)	−0.0004 (3)
N1	0.0147 (4)	0.0111 (4)	0.0185 (4)	0.0021 (4)	0.0029 (3)	0.0017 (4)
C1	0.0237 (6)	0.0355 (8)	0.0192 (6)	−0.0010 (6)	−0.0032 (5)	0.0023 (5)
C2	0.0167 (5)	0.0220 (6)	0.0170 (5)	−0.0033 (5)	0.0009 (4)	0.0018 (4)
C3	0.0177 (5)	0.0182 (6)	0.0210 (5)	0.0029 (4)	−0.0010 (4)	0.0019 (4)
C4	0.0190 (5)	0.0153 (5)	0.0196 (5)	0.0031 (4)	0.0008 (4)	−0.0010 (4)
C5	0.0139 (5)	0.0138 (5)	0.0154 (5)	−0.0007 (4)	0.0018 (4)	0.0007 (4)
C6	0.0194 (5)	0.0156 (5)	0.0191 (5)	0.0025 (4)	0.0033 (4)	−0.0012 (4)
C7	0.0227 (6)	0.0210 (6)	0.0172 (5)	0.0006 (5)	0.0026 (4)	−0.0029 (4)
C8	0.0134 (5)	0.0159 (5)	0.0163 (5)	−0.0014 (4)	0.0004 (4)	−0.0035 (4)
C9	0.0180 (5)	0.0186 (6)	0.0222 (5)	−0.0032 (5)	0.0028 (4)	0.0005 (5)

S1—O2	1.4323 (9)	C3—C4	1.3910 (16)
S1—O1	1.4354 (9)	C3—H3A	0.9500
S1—N1	1.6486 (10)	C4—C5	1.3899 (16)
S1—C5	1.7563 (12)	C4—H4A	0.9500
O3—C8	1.2141 (14)	C5—C6	1.3934 (16)
N1—C8	1.3964 (14)	C6—C7	1.3874 (17)
N1—H1N1	0.851 (19)	C6—H6A	0.9500
C1—C2	1.5066 (17)	C7—H7A	0.9500
C1—H1A	0.9800	C8—C9	1.4917 (17)
C1—H1B	0.9800	C9—H9A	0.9800
C1—H1C	0.9800	C9—H9B	0.9800
C2—C3	1.3936 (17)	C9—H9C	0.9800
C2—C7	1.3962 (18)
O2—S1—O1	119.27 (5)	C5—C4—C3	118.76 (11)
O2—S1—N1	104.10 (5)	C5—C4—H4A	120.6
O1—S1—N1	108.93 (5)	C3—C4—H4A	120.6
O2—S1—C5	109.15 (5)	C4—C5—C6	121.33 (11)
O1—S1—C5	108.64 (5)	C4—C5—S1	119.88 (9)
N1—S1—C5	105.92 (5)	C6—C5—S1	118.78 (9)
C8—N1—S1	123.71 (9)	C7—C6—C5	118.88 (11)
C8—N1—H1N1	121.2 (12)	C7—C6—H6A	120.6
S1—N1—H1N1	114.9 (12)	C5—C6—H6A	120.6
C2—C1—H1A	109.5	C6—C7—C2	121.05 (11)
C2—C1—H1B	109.5	C6—C7—H7A	119.5
H1A—C1—H1B	109.5	C2—C7—H7A	119.5
C2—C1—H1C	109.5	O3—C8—N1	120.50 (11)
H1A—C1—H1C	109.5	O3—C8—C9	125.13 (11)
H1B—C1—H1C	109.5	N1—C8—C9	114.37 (10)
C3—C2—C7	118.82 (11)	C8—C9—H9A	109.5
C3—C2—C1	120.60 (12)	C8—C9—H9B	109.5
C7—C2—C1	120.57 (12)	H9A—C9—H9B	109.5
C4—C3—C2	121.15 (11)	C8—C9—H9C	109.5
C4—C3—H3A	119.4	H9A—C9—H9C	109.5
C2—C3—H3A	119.4	H9B—C9—H9C	109.5
O2—S1—N1—C8	178.75 (9)	O2—S1—C5—C6	27.10 (11)
O1—S1—N1—C8	50.50 (11)	O1—S1—C5—C6	158.66 (9)
C5—S1—N1—C8	−66.20 (10)	N1—S1—C5—C6	−84.45 (10)
C7—C2—C3—C4	−0.19 (19)	C4—C5—C6—C7	−0.52 (18)
C1—C2—C3—C4	−179.65 (12)	S1—C5—C6—C7	179.77 (9)
C2—C3—C4—C5	0.09 (19)	C5—C6—C7—C2	0.41 (19)
C3—C4—C5—C6	0.27 (18)	C3—C2—C7—C6	−0.06 (19)
C3—C4—C5—S1	179.99 (9)	C1—C2—C7—C6	179.40 (12)
O2—S1—C5—C4	−152.62 (10)	S1—N1—C8—O3	4.19 (16)
O1—S1—C5—C4	−21.06 (11)	S1—N1—C8—C9	−175.99 (8)
N1—S1—C5—C4	95.83 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1i	0.85 (2)	2.14 (2)	2.9586 (14)	161.2 (17)
C9—H9A···O3ii	0.98	2.49	3.4623 (15)	175
C9—H9C···O3i	0.98	2.32	3.2760 (14)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1i	0.85 (2)	2.14 (2)	2.9586 (14)	161.2 (17)
C9—H9A⋯O3ii	0.98	2.49	3.4623 (15)	175
C9—H9C⋯O3i	0.98	2.32	3.2760 (14)	165

Symmetry codes: (i) ; (ii) .