N-(Phenyl-sulfon-yl)acetamide.

In the title compound, C(8)H(9)NO(3)S, the N-H bond is in an anti-periplanar conformation with respect to the C=O bond. The crystal packing is stabilized by N-H⋯O hydrogen bonds, generating C(4) chains propagating in [001].

Related literature

Sulfonamide drugs contain the sulfanilamide moiety, see: Maren (1976 ▶). The propensity for hydrogen bonding in the solid state, due to the presence of various hydrogen bond donors and acceptors, can give rise to polymorphism, see: Yang & Guillory (1972 ▶). For the hydrogen-bonding preferences of sulfonamides, see: Adsmond & Grant (2001 ▶). For related structures, see: Gowda et al. (2008 ▶, 2009 ▶).

Experimental

Crystal data

C8H9NO3S

M = 199.22

Tetragonal,

a = 7.9400 (5) Å

c = 15.288 (2) Å

V = 963.81 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 299 K

0.30 × 0.24 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.913, T max = 0.964

2706 measured reflections

1401 independent reflections

1214 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.100

S = 1.30

1401 reflections

121 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: Flack (1983 ▶), 378 Friedel pairs

Flack parameter: 0.11 (16)

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810015849/bt5256sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015849/bt5256Isup2.hkl

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

C8H9NO3S	Dx = 1.373 Mg m−3
Mr = 199.22	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P43	Cell parameters from 1337 reflections
Hall symbol: P 4cw	θ = 2.6–27.9°
a = 7.9400 (5) Å	µ = 0.31 mm−1
c = 15.288 (2) Å	T = 299 K
V = 963.81 (15) Å3	Rod, colourless
Z = 4	0.30 × 0.24 × 0.12 mm
F(000) = 416

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1401 independent reflections
Radiation source: fine-focus sealed tube	1214 reflections with I > 2σ(I)
graphite	Rint = 0.014
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −5→9
Tmin = 0.913, Tmax = 0.964	k = −9→5
2706 measured reflections	l = −18→19

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)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.100	w = 1/[σ2(Fo2) + (0.0165P)2 + 0.6175P] where P = (Fo2 + 2Fc2)/3
S = 1.30	(Δ/σ)max = 0.022
1401 reflections	Δρmax = 0.21 e Å−3
121 parameters	Δρmin = −0.24 e Å−3
2 restraints	Absolute structure: Flack (1983), 378 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.11 (16)

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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.

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
C1	0.1027 (6)	0.4526 (6)	−0.0895 (3)	0.0558 (12)
C2	0.1149 (6)	0.4033 (7)	−0.1756 (3)	0.0646 (14)
H2	0.1204	0.2895	−0.1896	0.078*
C3	0.1188 (7)	0.5227 (9)	−0.2413 (4)	0.0866 (18)
H3	0.1238	0.4899	−0.2996	0.104*
C4	0.1154 (8)	0.6897 (9)	−0.2194 (5)	0.099 (2)
H4	0.1202	0.7704	−0.2635	0.119*
C5	0.1051 (9)	0.7400 (8)	−0.1344 (7)	0.108 (3)
H5	0.1017	0.8542	−0.1209	0.129*
C6	0.0996 (7)	0.6210 (9)	−0.0676 (5)	0.0869 (19)
H6	0.0939	0.6543	−0.0093	0.104*
C7	0.4226 (6)	0.3105 (6)	0.0165 (3)	0.0550 (12)
C8	0.5621 (6)	0.3530 (7)	0.0779 (4)	0.0792 (17)
H8A	0.5555	0.2816	0.1285	0.095*
H8B	0.5523	0.4686	0.0956	0.095*
H8C	0.6684	0.3361	0.0492	0.095*
N1	0.2655 (5)	0.3259 (5)	0.0517 (2)	0.0543 (10)
H1N	0.250 (6)	0.373 (6)	0.1013 (19)	0.065*
O1	−0.0383 (4)	0.3502 (6)	0.0542 (3)	0.0969 (14)
O2	0.0878 (5)	0.1384 (5)	−0.0435 (2)	0.0849 (13)
O3	0.4421 (5)	0.2652 (5)	−0.0584 (2)	0.0725 (11)
S1	0.08988 (14)	0.30118 (19)	−0.00585 (8)	0.0633 (4)

	U11	U22	U33	U12	U13	U23
C1	0.048 (3)	0.059 (3)	0.060 (3)	0.004 (2)	−0.007 (2)	−0.015 (3)
C2	0.066 (3)	0.070 (3)	0.057 (3)	0.004 (3)	−0.008 (3)	−0.014 (3)
C3	0.089 (5)	0.098 (5)	0.073 (4)	0.002 (3)	−0.017 (3)	0.007 (4)
C4	0.088 (5)	0.088 (5)	0.122 (6)	−0.005 (4)	−0.026 (4)	0.023 (5)
C5	0.115 (6)	0.059 (4)	0.149 (7)	0.003 (4)	−0.028 (5)	−0.020 (5)
C6	0.084 (4)	0.084 (5)	0.093 (4)	−0.002 (3)	−0.017 (4)	−0.028 (4)
C7	0.046 (3)	0.057 (3)	0.062 (3)	0.004 (2)	0.005 (2)	0.004 (2)
C8	0.043 (3)	0.105 (4)	0.089 (4)	0.003 (3)	−0.005 (3)	−0.001 (4)
N1	0.041 (2)	0.079 (3)	0.043 (2)	−0.0046 (18)	0.0041 (18)	−0.017 (2)
O1	0.0412 (19)	0.173 (4)	0.077 (2)	−0.004 (2)	0.009 (2)	−0.017 (3)
O2	0.109 (3)	0.073 (3)	0.074 (2)	−0.029 (2)	−0.019 (2)	−0.012 (2)
O3	0.069 (2)	0.090 (3)	0.059 (2)	0.019 (2)	0.0191 (18)	0.0000 (19)
S1	0.0454 (6)	0.0888 (10)	0.0557 (6)	−0.0127 (6)	−0.0023 (7)	−0.0144 (7)

C1—C6	1.378 (7)	C6—H6	0.9300
C1—C2	1.377 (6)	C7—O3	1.210 (5)
C1—S1	1.758 (5)	C7—N1	1.365 (6)
C2—C3	1.380 (7)	C7—C8	1.491 (6)
C2—H2	0.9300	C8—H8A	0.9600
C3—C4	1.367 (9)	C8—H8B	0.9600
C3—H3	0.9300	C8—H8C	0.9600
C4—C5	1.363 (9)	N1—S1	1.660 (4)
C4—H4	0.9300	N1—H1N	0.854 (19)
C5—C6	1.393 (10)	O1—S1	1.425 (4)
C5—H5	0.9300	O2—S1	1.415 (4)
C6—C1—C2	120.7 (5)	O3—C7—N1	121.1 (5)
C6—C1—S1	119.0 (5)	O3—C7—C8	124.7 (5)
C2—C1—S1	120.3 (4)	N1—C7—C8	114.2 (4)
C3—C2—C1	120.1 (5)	C7—C8—H8A	109.5
C3—C2—H2	120.0	C7—C8—H8B	109.5
C1—C2—H2	120.0	H8A—C8—H8B	109.5
C4—C3—C2	119.2 (6)	C7—C8—H8C	109.5
C4—C3—H3	120.4	H8A—C8—H8C	109.5
C2—C3—H3	120.4	H8B—C8—H8C	109.5
C5—C4—C3	121.2 (7)	C7—N1—S1	123.2 (3)
C5—C4—H4	119.4	C7—N1—H1N	122 (3)
C3—C4—H4	119.4	S1—N1—H1N	113 (3)
C4—C5—C6	120.2 (6)	O2—S1—O1	120.2 (2)
C4—C5—H5	119.9	O2—S1—N1	109.5 (2)
C6—C5—H5	119.9	O1—S1—N1	103.1 (2)
C1—C6—C5	118.6 (6)	O2—S1—C1	109.2 (2)
C1—C6—H6	120.7	O1—S1—C1	108.8 (3)
C5—C6—H6	120.7	N1—S1—C1	104.8 (2)
C6—C1—C2—C3	−2.0 (8)	C7—N1—S1—O2	58.3 (5)
S1—C1—C2—C3	177.7 (4)	C7—N1—S1—O1	−172.6 (4)
C1—C2—C3—C4	1.9 (8)	C7—N1—S1—C1	−58.8 (4)
C2—C3—C4—C5	−1.2 (11)	C6—C1—S1—O2	177.4 (4)
C3—C4—C5—C6	0.7 (12)	C2—C1—S1—O2	−2.3 (5)
C2—C1—C6—C5	1.5 (8)	C6—C1—S1—O1	44.4 (5)
S1—C1—C6—C5	−178.3 (5)	C2—C1—S1—O1	−135.3 (4)
C4—C5—C6—C1	−0.8 (10)	C6—C1—S1—N1	−65.3 (4)
O3—C7—N1—S1	−5.6 (7)	C2—C1—S1—N1	114.9 (4)
C8—C7—N1—S1	174.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3i	0.85 (2)	2.02 (3)	2.823 (5)	156 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3i	0.85 (2)	2.02 (3)	2.823 (5)	156 (5)

Symmetry code: (i) .