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

In the title compound, C(10)H(13)NO(3)S, the conformations of the N-H and C=O bonds of the SO(2)-NH-CO-C segment 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 -66.7 (2)°. The crystal structure features inversion-related dimers linked by pairs of N-H⋯O(S) hydrogen bonds.

Related literature

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 ▶); on the structures of N-(substitutedphenyl­sulfon­yl)-substitutedamides, see: Shakuntala et al. (2011 ▶) and on the oxidative strengths of N-chloro, N-aryl­sulfonamides, see: Gowda & Kumar (2003 ▶).

Experimental

Crystal data

C10H13NO3S

M = 227.27

Monoclinic,

a = 8.3050 (8) Å

b = 13.339 (1) Å

c = 9.9948 (9) Å

β = 97.876 (9)°

V = 1096.78 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 293 K

0.44 × 0.32 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.886, T max = 0.956

4277 measured reflections

2241 independent reflections

1607 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.108

S = 1.04

2241 reflections

140 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.35 e Å−3

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/S1600536811014164/ds2108sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014164/ds2108Isup2.hkl

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

C10H13NO3S	F(000) = 480
Mr = 227.27	Dx = 1.376 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1271 reflections
a = 8.3050 (8) Å	θ = 2.6–27.8°
b = 13.339 (1) Å	µ = 0.28 mm−1
c = 9.9948 (9) Å	T = 293 K
β = 97.876 (9)°	Prism, colourless
V = 1096.78 (17) Å3	0.44 × 0.32 × 0.16 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2241 independent reflections
Radiation source: fine-focus sealed tube	1607 reflections with I > 2σ(I)
graphite	Rint = 0.017
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 = −10→10
Tmin = 0.886, Tmax = 0.956	k = −11→16
4277 measured reflections	l = −12→7

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0396P)2 + 0.5309P] where P = (Fo2 + 2Fc2)/3
2241 reflections	(Δ/σ)max < 0.001
140 parameters	Δρmax = 0.20 e Å−3
1 restraint	Δρmin = −0.35 e Å−3

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	0.6604 (2)	0.45905 (16)	0.3478 (2)	0.0403 (5)
C2	0.5397 (3)	0.38655 (18)	0.3512 (2)	0.0456 (6)
C3	0.5387 (3)	0.3371 (2)	0.4736 (3)	0.0586 (7)
H3	0.4597	0.2886	0.4800	0.070*
C4	0.6499 (3)	0.3571 (2)	0.5856 (3)	0.0622 (7)
H4	0.6454	0.3221	0.6655	0.075*
C5	0.7679 (3)	0.4288 (2)	0.5794 (2)	0.0584 (7)
H5	0.8431	0.4427	0.6550	0.070*
C6	0.7736 (3)	0.47990 (19)	0.4607 (2)	0.0484 (6)
H6	0.8530	0.5284	0.4557	0.058*
C7	0.8782 (3)	0.40395 (18)	0.0980 (2)	0.0461 (6)
C8	0.9020 (3)	0.34442 (19)	−0.0249 (2)	0.0501 (6)
H8A	0.9198	0.3903	−0.0967	0.060*
H8B	0.8032	0.3072	−0.0548	0.060*
C9	1.0421 (3)	0.2722 (2)	−0.0023 (3)	0.0646 (7)
H9A	1.0251	0.2259	0.0679	0.078*
H9B	1.1412	0.3086	0.0237	0.078*
H9C	1.0495	0.2359	−0.0843	0.078*
C10	0.4116 (3)	0.3615 (2)	0.2348 (3)	0.0633 (7)
H10A	0.4601	0.3585	0.1530	0.076*
H10B	0.3288	0.4122	0.2264	0.076*
H10C	0.3641	0.2977	0.2506	0.076*
N1	0.7295 (2)	0.45380 (16)	0.08882 (19)	0.0497 (5)
H1N	0.664 (3)	0.4451 (19)	0.020 (2)	0.060*
O1	0.5187 (2)	0.56595 (14)	0.14397 (17)	0.0616 (5)
O2	0.8011 (2)	0.60402 (13)	0.23614 (19)	0.0673 (5)
O3	0.9760 (2)	0.41109 (16)	0.19851 (18)	0.0681 (5)
S1	0.67655 (7)	0.53152 (5)	0.20265 (6)	0.04798 (19)

	U11	U22	U33	U12	U13	U23
C1	0.0367 (11)	0.0465 (13)	0.0363 (11)	0.0061 (10)	0.0005 (9)	−0.0056 (10)
C2	0.0397 (12)	0.0487 (14)	0.0474 (13)	0.0064 (10)	0.0020 (10)	−0.0065 (11)
C3	0.0538 (14)	0.0620 (16)	0.0623 (17)	0.0026 (13)	0.0164 (12)	0.0013 (14)
C4	0.0675 (17)	0.0768 (19)	0.0443 (14)	0.0150 (15)	0.0145 (13)	0.0073 (14)
C5	0.0563 (15)	0.0782 (19)	0.0376 (13)	0.0161 (14)	−0.0048 (11)	−0.0056 (13)
C6	0.0405 (12)	0.0595 (15)	0.0426 (12)	0.0029 (11)	−0.0034 (9)	−0.0057 (11)
C7	0.0381 (11)	0.0577 (15)	0.0414 (12)	−0.0047 (11)	0.0019 (10)	0.0041 (11)
C8	0.0447 (13)	0.0606 (16)	0.0448 (13)	−0.0051 (11)	0.0055 (10)	0.0008 (12)
C9	0.0612 (16)	0.0646 (17)	0.0684 (18)	0.0062 (14)	0.0103 (14)	−0.0021 (15)
C10	0.0477 (14)	0.0692 (17)	0.0695 (17)	−0.0068 (13)	−0.0049 (12)	−0.0150 (14)
N1	0.0429 (11)	0.0684 (14)	0.0352 (10)	0.0068 (10)	−0.0046 (8)	−0.0063 (10)
O1	0.0666 (11)	0.0681 (11)	0.0458 (10)	0.0258 (9)	−0.0083 (8)	−0.0008 (8)
O2	0.0823 (13)	0.0584 (11)	0.0592 (11)	−0.0211 (10)	0.0033 (9)	−0.0005 (9)
O3	0.0474 (10)	0.0995 (15)	0.0524 (11)	0.0089 (10)	−0.0105 (8)	−0.0127 (10)
S1	0.0515 (3)	0.0502 (4)	0.0396 (3)	0.0034 (3)	−0.0036 (2)	0.0002 (3)

C1—C6	1.394 (3)	C7—C8	1.499 (3)
C1—C2	1.397 (3)	C8—C9	1.504 (3)
C1—S1	1.763 (2)	C8—H8A	0.9700
C2—C3	1.391 (3)	C8—H8B	0.9700
C2—C10	1.503 (3)	C9—H9A	0.9600
C3—C4	1.377 (4)	C9—H9B	0.9600
C3—H3	0.9300	C9—H9C	0.9600
C4—C5	1.377 (4)	C10—H10A	0.9600
C4—H4	0.9300	C10—H10B	0.9600
C5—C6	1.375 (3)	C10—H10C	0.9600
C5—H5	0.9300	N1—S1	1.643 (2)
C6—H6	0.9300	N1—H1N	0.822 (16)
C7—O3	1.206 (3)	O1—S1	1.4363 (17)
C7—N1	1.395 (3)	O2—S1	1.4219 (18)
C6—C1—C2	121.7 (2)	C7—C8—H8B	108.8
C6—C1—S1	115.96 (18)	C9—C8—H8B	108.8
C2—C1—S1	122.38 (16)	H8A—C8—H8B	107.7
C3—C2—C1	116.2 (2)	C8—C9—H9A	109.5
C3—C2—C10	119.1 (2)	C8—C9—H9B	109.5
C1—C2—C10	124.7 (2)	H9A—C9—H9B	109.5
C4—C3—C2	122.6 (3)	C8—C9—H9C	109.5
C4—C3—H3	118.7	H9A—C9—H9C	109.5
C2—C3—H3	118.7	H9B—C9—H9C	109.5
C3—C4—C5	120.0 (3)	C2—C10—H10A	109.5
C3—C4—H4	120.0	C2—C10—H10B	109.5
C5—C4—H4	120.0	H10A—C10—H10B	109.5
C6—C5—C4	119.4 (2)	C2—C10—H10C	109.5
C6—C5—H5	120.3	H10A—C10—H10C	109.5
C4—C5—H5	120.3	H10B—C10—H10C	109.5
C5—C6—C1	120.1 (2)	C7—N1—S1	125.02 (16)
C5—C6—H6	120.0	C7—N1—H1N	117.6 (18)
C1—C6—H6	120.0	S1—N1—H1N	117.3 (18)
O3—C7—N1	120.4 (2)	O2—S1—O1	118.19 (12)
O3—C7—C8	125.1 (2)	O2—S1—N1	109.70 (11)
N1—C7—C8	114.42 (19)	O1—S1—N1	103.59 (10)
C7—C8—C9	113.7 (2)	O2—S1—C1	108.31 (11)
C7—C8—H8A	108.8	O1—S1—C1	110.06 (10)
C9—C8—H8A	108.8	N1—S1—C1	106.35 (11)
C6—C1—C2—C3	0.3 (3)	N1—C7—C8—C9	−166.1 (2)
S1—C1—C2—C3	−178.22 (17)	O3—C7—N1—S1	4.7 (4)
C6—C1—C2—C10	178.7 (2)	C8—C7—N1—S1	−174.80 (17)
S1—C1—C2—C10	0.1 (3)	C7—N1—S1—O2	50.2 (2)
C1—C2—C3—C4	−0.4 (4)	C7—N1—S1—O1	177.3 (2)
C10—C2—C3—C4	−178.8 (2)	C7—N1—S1—C1	−66.7 (2)
C2—C3—C4—C5	0.3 (4)	C6—C1—S1—O2	−4.0 (2)
C3—C4—C5—C6	−0.1 (4)	C2—C1—S1—O2	174.62 (18)
C4—C5—C6—C1	0.1 (4)	C6—C1—S1—O1	−134.60 (17)
C2—C1—C6—C5	−0.2 (3)	C2—C1—S1—O1	44.0 (2)
S1—C1—C6—C5	178.44 (18)	C6—C1—S1—N1	113.82 (18)
O3—C7—C8—C9	14.4 (4)	C2—C1—S1—N1	−67.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.82 (2)	2.08 (2)	2.901 (2)	173 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.82 (2)	2.08 (2)	2.901 (2)	173 (3)

Symmetry code: (i) .