N-(4-Chloro-phenyl-sulfon-yl)-2-methyl-propanamide.

In the crystal structure of the title compound, C(10)H(12)ClNO(3)S, the N-C bond in the C-SO(2)-NH-C segment has a gauche torsion with respect to the S=O bonds. The mol-ecule is twisted at the S atom with a C-S-N-C torsion angle of -62.3 (3)°. The benzene ring and the SO(2)-NH-CO-C segment form a dihedral angle of 89.3 (1)°. In the crystal, mol-ecules are linked by pairs of N-H⋯O hydrogen bonds into inversion dimers.

Related literature

For the sulfanilamide moiety in sulfonamide drugs, see: Maren (1976 ▶). For its ability to form hydrogen bonds in the solid state, see: Yang & Guillory (1972 ▶). For hydrogen-bonding modes of sulfonamides, see: Adsmond & Grant (2001 ▶). For our studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Arjunan et al. (2004 ▶), on N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007 ▶), on N-(ar­yl)-aryl­sulfonamides, see: Gowda et al. (2003 ▶) and on N-(aryl­sulfon­yl)-amides, see: Gowda et al. (2008 ▶); Shakuntala et al. (2011 ▶).

Experimental

Crystal data

C10H12ClNO3S

M = 261.72

Triclinic,

a = 6.207 (1) Å

b = 10.395 (3) Å

c = 10.497 (3) Å

α = 70.150 (2)°

β = 79.160 (2)°

γ = 86.010 (2)°

V = 625.7 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.46 mm−1

T = 293 K

0.46 × 0.20 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan CrysAlis RED (Oxford Diffraction, 2009 ▶) T min = 0.815, T max = 0.964

3846 measured reflections

2476 independent reflections

1842 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.126

S = 1.19

2476 reflections

148 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.31 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 datablock(s) I, global. DOI: 10.1107/S1600536811031394/nc2243sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031394/nc2243Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811031394/nc2243Isup3.cml

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

C10H12ClNO3S	Z = 2
Mr = 261.72	F(000) = 272
Triclinic, P1	Dx = 1.389 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.207 (1) Å	Cell parameters from 1240 reflections
b = 10.395 (3) Å	θ = 3.3–27.8°
c = 10.497 (3) Å	µ = 0.46 mm−1
α = 70.150 (2)°	T = 293 K
β = 79.160 (2)°	Plate, colourless
γ = 86.010 (2)°	0.46 × 0.20 × 0.08 mm
V = 625.7 (3) Å3

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2476 independent reflections
Radiation source: fine-focus sealed tube	1842 reflections with I > 2σ(I)
graphite	Rint = 0.014
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 3.3°
Absorption correction: multi-scan CrysAlis RED (Oxford Diffraction, 2009)	h = −7→7
Tmin = 0.815, Tmax = 0.964	k = −12→12
3846 measured reflections	l = −13→13

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.19	w = 1/[σ2(Fo2) + (0.0233P)2 + 0.632P] where P = (Fo2 + 2Fc2)/3
2476 reflections	(Δ/σ)max = 0.001
148 parameters	Δρmax = 0.28 e Å−3
1 restraint	Δρmin = −0.31 e Å−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
C1	0.1905 (5)	0.2375 (3)	0.9043 (3)	0.0475 (7)
C2	−0.0001 (6)	0.2717 (4)	0.8506 (4)	0.0610 (9)
H2	−0.0818	0.3477	0.8593	0.073*
C3	−0.0683 (6)	0.1930 (4)	0.7844 (4)	0.0670 (10)
H3	−0.1957	0.2156	0.7468	0.080*
C4	0.0535 (7)	0.0805 (3)	0.7742 (4)	0.0638 (10)
C5	0.2423 (7)	0.0456 (4)	0.8278 (4)	0.0709 (11)
H5	0.3221	−0.0315	0.8207	0.085*
C6	0.3124 (6)	0.1255 (3)	0.8920 (4)	0.0612 (9)
H6	0.4421	0.1040	0.9271	0.073*
C7	0.4540 (6)	0.5278 (4)	0.7543 (4)	0.0578 (9)
C8	0.4194 (7)	0.6715 (4)	0.6608 (4)	0.0716 (11)
H8	0.3561	0.7263	0.7187	0.086*
C9	0.2542 (9)	0.6652 (6)	0.5756 (5)	0.1190 (19)
H9A	0.1202	0.6271	0.6350	0.143*
H9B	0.3103	0.6089	0.5208	0.143*
H9C	0.2265	0.7558	0.5165	0.143*
C10	0.6291 (10)	0.7353 (6)	0.5780 (6)	0.151 (3)
H10A	0.6959	0.6822	0.5219	0.182*
H10B	0.7258	0.7386	0.6383	0.182*
H10C	0.6015	0.8265	0.5202	0.182*
N1	0.3069 (5)	0.4914 (3)	0.8767 (3)	0.0560 (7)
H1N	0.200 (4)	0.541 (3)	0.892 (4)	0.067*
O1	0.0960 (4)	0.3525 (3)	1.0924 (2)	0.0729 (7)
O2	0.4794 (4)	0.2850 (3)	1.0314 (3)	0.0714 (7)
O3	0.5885 (4)	0.4482 (3)	0.7273 (3)	0.0863 (9)
Cl1	−0.0354 (3)	−0.01843 (12)	0.69033 (14)	0.1076 (5)
S1	0.27563 (15)	0.33738 (9)	0.99054 (9)	0.0559 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0524 (18)	0.0386 (16)	0.0429 (17)	0.0085 (14)	−0.0084 (14)	−0.0043 (13)
C2	0.055 (2)	0.056 (2)	0.074 (2)	0.0148 (16)	−0.0162 (18)	−0.0244 (18)
C3	0.063 (2)	0.063 (2)	0.072 (2)	0.0024 (18)	−0.0210 (19)	−0.014 (2)
C4	0.090 (3)	0.0428 (19)	0.053 (2)	−0.0118 (18)	−0.0140 (19)	−0.0066 (16)
C5	0.095 (3)	0.0419 (19)	0.077 (3)	0.0201 (19)	−0.026 (2)	−0.0180 (18)
C6	0.068 (2)	0.0471 (19)	0.070 (2)	0.0184 (17)	−0.0255 (19)	−0.0175 (17)
C7	0.052 (2)	0.059 (2)	0.059 (2)	0.0048 (17)	−0.0146 (17)	−0.0148 (17)
C8	0.086 (3)	0.062 (2)	0.057 (2)	0.007 (2)	−0.012 (2)	−0.0084 (18)
C9	0.146 (5)	0.114 (4)	0.095 (4)	0.039 (4)	−0.060 (4)	−0.020 (3)
C10	0.123 (5)	0.128 (5)	0.133 (5)	−0.026 (4)	−0.001 (4)	0.041 (4)
N1	0.0637 (19)	0.0447 (16)	0.0567 (17)	0.0105 (13)	−0.0102 (15)	−0.0155 (13)
O1	0.0929 (19)	0.0657 (16)	0.0489 (14)	0.0221 (14)	−0.0029 (13)	−0.0142 (12)
O2	0.0769 (17)	0.0681 (16)	0.0755 (17)	0.0171 (13)	−0.0381 (14)	−0.0221 (13)
O3	0.0719 (18)	0.087 (2)	0.0815 (19)	0.0296 (15)	−0.0026 (15)	−0.0156 (16)
Cl1	0.1677 (13)	0.0641 (7)	0.1053 (9)	−0.0180 (7)	−0.0502 (9)	−0.0294 (6)
S1	0.0676 (6)	0.0489 (5)	0.0494 (5)	0.0139 (4)	−0.0159 (4)	−0.0140 (4)

C1—C6	1.374 (4)	C7—C8	1.510 (5)
C1—C2	1.378 (4)	C8—C10	1.481 (6)
C1—S1	1.753 (3)	C8—C9	1.500 (6)
C2—C3	1.370 (5)	C8—H8	0.9800
C2—H2	0.9300	C9—H9A	0.9600
C3—C4	1.372 (5)	C9—H9B	0.9600
C3—H3	0.9300	C9—H9C	0.9600
C4—C5	1.368 (5)	C10—H10A	0.9600
C4—Cl1	1.736 (4)	C10—H10B	0.9600
C5—C6	1.368 (5)	C10—H10C	0.9600
C5—H5	0.9300	N1—S1	1.639 (3)
C6—H6	0.9300	N1—H1N	0.840 (18)
C7—O3	1.199 (4)	O1—S1	1.433 (2)
C7—N1	1.380 (4)	O2—S1	1.425 (2)
C6—C1—C2	120.7 (3)	C10—C8—H8	107.9
C6—C1—S1	119.9 (3)	C9—C8—H8	107.9
C2—C1—S1	119.4 (2)	C7—C8—H8	107.9
C3—C2—C1	119.5 (3)	C8—C9—H9A	109.5
C3—C2—H2	120.2	C8—C9—H9B	109.5
C1—C2—H2	120.2	H9A—C9—H9B	109.5
C2—C3—C4	119.2 (3)	C8—C9—H9C	109.5
C2—C3—H3	120.4	H9A—C9—H9C	109.5
C4—C3—H3	120.4	H9B—C9—H9C	109.5
C5—C4—C3	121.5 (3)	C8—C10—H10A	109.5
C5—C4—Cl1	119.8 (3)	C8—C10—H10B	109.5
C3—C4—Cl1	118.7 (3)	H10A—C10—H10B	109.5
C6—C5—C4	119.2 (3)	C8—C10—H10C	109.5
C6—C5—H5	120.4	H10A—C10—H10C	109.5
C4—C5—H5	120.4	H10B—C10—H10C	109.5
C5—C6—C1	119.8 (3)	C7—N1—S1	125.8 (2)
C5—C6—H6	120.1	C7—N1—H1N	122 (3)
C1—C6—H6	120.1	S1—N1—H1N	110 (3)
O3—C7—N1	121.2 (3)	O2—S1—O1	119.07 (16)
O3—C7—C8	125.4 (3)	O2—S1—N1	110.56 (16)
N1—C7—C8	113.3 (3)	O1—S1—N1	103.75 (15)
C10—C8—C9	113.5 (4)	O2—S1—C1	108.79 (15)
C10—C8—C7	111.6 (4)	O1—S1—C1	108.78 (17)
C9—C8—C7	107.7 (4)	N1—S1—C1	104.95 (15)
C6—C1—C2—C3	0.0 (5)	N1—C7—C8—C9	−87.3 (4)
S1—C1—C2—C3	−179.3 (3)	O3—C7—N1—S1	−7.0 (5)
C1—C2—C3—C4	0.7 (6)	C8—C7—N1—S1	170.6 (3)
C2—C3—C4—C5	−0.5 (6)	C7—N1—S1—O2	54.8 (3)
C2—C3—C4—Cl1	179.9 (3)	C7—N1—S1—O1	−176.4 (3)
C3—C4—C5—C6	−0.6 (6)	C7—N1—S1—C1	−62.3 (3)
Cl1—C4—C5—C6	179.1 (3)	C6—C1—S1—O2	2.9 (3)
C4—C5—C6—C1	1.4 (6)	C2—C1—S1—O2	−177.8 (3)
C2—C1—C6—C5	−1.1 (5)	C6—C1—S1—O1	−128.3 (3)
S1—C1—C6—C5	178.3 (3)	C2—C1—S1—O1	51.1 (3)
O3—C7—C8—C10	−35.0 (6)	C6—C1—S1—N1	121.2 (3)
N1—C7—C8—C10	147.5 (4)	C2—C1—S1—N1	−59.4 (3)
O3—C7—C8—C9	90.2 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.84 (2)	2.08 (2)	2.912 (4)	169 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.84 (2)	2.08 (2)	2.912 (4)	169 (3)

Symmetry code: (i) .