N-(2-Methyl-phenyl-sulfon-yl)acetamide.

In the mol-ecular structure of the title compound, C(9)H(11)NO(3)S, the N-H and C=O bonds are anti to each other, while the amide H atom is syn with respect to the ortho-methyl group in the benzene ring. The C-S-N-C torsion angle is -58.2 (2)°, indicating a twist in the mol-ecule. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into chains along the c axis.

Related literature

For the sulfanilamide moiety in sulfonamide drugs, see: Maren (1976 ▶). For hydrogen bonding modes of sulfonamides, see: Adsmond & Grant (2001 ▶). For our study of the effect of substituents on the structures of N-(ar­yl)-amides, see: Gowda et al. (2004 ▶). For background to the structures of N-(substituted phenyl­sulfon­yl)-substituted-amides, see: Gowda et al. (2010 ▶); Shakuntala et al. (2011 ▶) and for the oxidative strengths of N-chloro, N-aryl­sulfonamides, see: Gowda & Kumar (2003 ▶).

Experimental

Crystal data

C9H11NO3S

M = 213.25

Tetragonal,

a = 7.9804 (5) Å

c = 16.749 (1) Å

V = 1066.69 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 293 K

0.40 × 0.18 × 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 = 0.895, T max = 0.967

4245 measured reflections

1944 independent reflections

1690 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.086

S = 1.08

1944 reflections

132 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.17 e Å−3

Absolute structure: Flack (1983 ▶), 824 Friedel pairs

Flack parameter: 0.03 (9)

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/S1600536811014218/tk2737sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014218/tk2737Isup2.hkl

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

C9H11NO3S	Dx = 1.328 Mg m−3
Mr = 213.25	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P43	Cell parameters from 1894 reflections
Hall symbol: P 4cw	θ = 2.5–27.8°
a = 7.9804 (5) Å	µ = 0.29 mm−1
c = 16.749 (1) Å	T = 293 K
V = 1066.69 (11) Å3	Prism, colourless
Z = 4	0.40 × 0.18 × 0.12 mm
F(000) = 448

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1944 independent reflections
Radiation source: fine-focus sealed tube	1690 reflections with I > 2σ(I)
graphite	Rint = 0.016
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 = −9→5
Tmin = 0.895, Tmax = 0.967	k = −6→9
4245 measured reflections	l = −17→20

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)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.086	w = 1/[σ2(Fo2) + (0.0453P)2 + 0.1227P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.016
1944 reflections	Δρmax = 0.14 e Å−3
132 parameters	Δρmin = −0.17 e Å−3
2 restraints	Absolute structure: Flack (1983), 824 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.03 (9)

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

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
C1	0.0401 (3)	0.5352 (3)	0.16636 (17)	0.0418 (6)
C2	0.0148 (3)	0.3636 (3)	0.15630 (19)	0.0534 (7)
C3	−0.0178 (4)	0.2719 (4)	0.2248 (3)	0.0758 (11)
H3	−0.0359	0.1571	0.2205	0.091*
C4	−0.0243 (5)	0.3456 (5)	0.2992 (2)	0.0844 (12)
H4	−0.0458	0.2805	0.3440	0.101*
C5	0.0008 (4)	0.5134 (5)	0.3071 (2)	0.0730 (10)
H5	−0.0034	0.5631	0.3573	0.088*
C6	0.0326 (4)	0.6095 (4)	0.24026 (19)	0.0571 (7)
H6	0.0490	0.7244	0.2452	0.069*
C7	0.4165 (3)	0.6071 (3)	0.10946 (17)	0.0462 (6)
C8	0.5725 (3)	0.5282 (5)	0.0766 (2)	0.0738 (10)
H8A	0.6102	0.5908	0.0310	0.089*
H8B	0.5489	0.4149	0.0608	0.089*
H8C	0.6582	0.5283	0.1168	0.089*
C9	0.0213 (5)	0.2751 (4)	0.0766 (3)	0.0830 (11)
H9A	0.1276	0.2961	0.0517	0.100*
H9B	−0.0669	0.3162	0.0429	0.100*
H9C	0.0075	0.1568	0.0845	0.100*
N1	0.2818 (3)	0.6051 (3)	0.05903 (12)	0.0413 (5)
H1N	0.278 (3)	0.556 (3)	0.0138 (12)	0.050*
O1	−0.0096 (3)	0.6269 (3)	0.01708 (12)	0.0644 (6)
O2	0.0971 (3)	0.8346 (2)	0.11214 (13)	0.0632 (6)
O3	0.4067 (2)	0.6678 (3)	0.17544 (11)	0.0588 (5)
S1	0.09057 (8)	0.66608 (8)	0.08490 (5)	0.04393 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0313 (12)	0.0414 (14)	0.0526 (15)	0.0022 (11)	0.0085 (11)	−0.0017 (12)
C2	0.0416 (15)	0.0414 (15)	0.077 (2)	0.0004 (12)	0.0128 (14)	−0.0002 (14)
C3	0.068 (2)	0.0495 (18)	0.110 (3)	0.0058 (16)	0.027 (2)	0.017 (2)
C4	0.078 (2)	0.090 (3)	0.085 (3)	0.011 (2)	0.030 (2)	0.033 (2)
C5	0.069 (2)	0.098 (3)	0.0526 (19)	0.0076 (18)	0.0181 (17)	0.0058 (18)
C6	0.0480 (16)	0.0596 (17)	0.0637 (18)	0.0013 (13)	0.0148 (14)	−0.0082 (16)
C7	0.0392 (14)	0.0478 (14)	0.0515 (17)	−0.0071 (11)	−0.0043 (11)	−0.0001 (13)
C8	0.0401 (15)	0.102 (3)	0.080 (2)	0.0051 (15)	0.0006 (17)	−0.012 (2)
C9	0.084 (2)	0.0521 (18)	0.112 (3)	−0.0123 (16)	0.020 (2)	−0.030 (2)
N1	0.0379 (11)	0.0493 (12)	0.0366 (12)	−0.0012 (9)	0.0021 (9)	−0.0061 (9)
O1	0.0510 (12)	0.0821 (16)	0.0601 (14)	0.0057 (10)	−0.0138 (10)	0.0055 (12)
O2	0.0717 (13)	0.0375 (10)	0.0806 (15)	0.0068 (9)	0.0170 (11)	0.0028 (10)
O3	0.0577 (12)	0.0760 (14)	0.0426 (11)	−0.0075 (10)	−0.0091 (9)	−0.0100 (10)
S1	0.0385 (3)	0.0424 (3)	0.0509 (4)	0.0049 (3)	0.0006 (3)	0.0015 (3)

C1—C6	1.374 (4)	C7—N1	1.367 (3)
C1—C2	1.395 (4)	C7—C8	1.500 (4)
C1—S1	1.765 (3)	C8—H8A	0.9600
C2—C3	1.386 (5)	C8—H8B	0.9600
C2—C9	1.511 (5)	C8—H8C	0.9600
C3—C4	1.378 (5)	C9—H9A	0.9600
C3—H3	0.9300	C9—H9B	0.9600
C4—C5	1.361 (6)	C9—H9C	0.9600
C4—H4	0.9300	N1—S1	1.659 (2)
C5—C6	1.380 (5)	N1—H1N	0.855 (17)
C5—H5	0.9300	O1—S1	1.424 (2)
C6—H6	0.9300	O2—S1	1.4213 (19)
C7—O3	1.209 (3)
C6—C1—C2	121.8 (3)	C7—C8—H8A	109.5
C6—C1—S1	116.8 (2)	C7—C8—H8B	109.5
C2—C1—S1	121.4 (2)	H8A—C8—H8B	109.5
C3—C2—C1	116.5 (3)	C7—C8—H8C	109.5
C3—C2—C9	119.4 (3)	H8A—C8—H8C	109.5
C1—C2—C9	124.1 (3)	H8B—C8—H8C	109.5
C4—C3—C2	122.0 (3)	C2—C9—H9A	109.5
C4—C3—H3	119.0	C2—C9—H9B	109.5
C2—C3—H3	119.0	H9A—C9—H9B	109.5
C5—C4—C3	120.2 (3)	C2—C9—H9C	109.5
C5—C4—H4	119.9	H9A—C9—H9C	109.5
C3—C4—H4	119.9	H9B—C9—H9C	109.5
C4—C5—C6	119.6 (3)	C7—N1—S1	123.94 (18)
C4—C5—H5	120.2	C7—N1—H1N	125.3 (19)
C6—C5—H5	120.2	S1—N1—H1N	109.7 (19)
C1—C6—C5	119.9 (3)	O2—S1—O1	119.00 (13)
C1—C6—H6	120.0	O2—S1—N1	109.12 (11)
C5—C6—H6	120.0	O1—S1—N1	104.10 (12)
O3—C7—N1	121.2 (2)	O2—S1—C1	108.68 (13)
O3—C7—C8	123.9 (3)	O1—S1—C1	110.99 (13)
N1—C7—C8	114.9 (3)	N1—S1—C1	103.79 (11)
C6—C1—C2—C3	−0.2 (4)	O3—C7—N1—S1	−6.3 (4)
S1—C1—C2—C3	177.5 (2)	C8—C7—N1—S1	173.3 (2)
C6—C1—C2—C9	180.0 (3)	C7—N1—S1—O2	57.5 (3)
S1—C1—C2—C9	−2.3 (4)	C7—N1—S1—O1	−174.5 (2)
C1—C2—C3—C4	−0.3 (5)	C7—N1—S1—C1	−58.2 (2)
C9—C2—C3—C4	179.6 (3)	C6—C1—S1—O2	−6.2 (3)
C2—C3—C4—C5	0.3 (6)	C2—C1—S1—O2	176.0 (2)
C3—C4—C5—C6	0.1 (5)	C6—C1—S1—O1	−138.9 (2)
C2—C1—C6—C5	0.6 (4)	C2—C1—S1—O1	43.3 (2)
S1—C1—C6—C5	−177.3 (2)	C6—C1—S1—N1	109.8 (2)
C4—C5—C6—C1	−0.5 (5)	C2—C1—S1—N1	−68.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3i	0.86 (2)	1.95 (2)	2.770 (3)	162 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3i	0.86 (2)	1.95 (2)	2.770 (3)	162 (3)

Symmetry code: (i) .