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

In the title compound, C(10)H(12)ClNO(3)S, the amide H atom is syn with respect to the ortho-chloro group in the benzene ring and the C-S-N-C torsion angle is 64.35 (16)°. The benzene ring and the SO(2)-NH-CO-C segment form a dihedral angle of 87.4 (1)°. The crystal structure features inversion-related dimers linked by pairs of N-H⋯O hydrogen bonds.

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 the hydrogen-bonding characteristics of sulfonamides, see; Adsmond & Grant (2001 ▶). For the effect of substituents on the crystal structures of sulfono­amides, see: Gowda et al. (2008 ▶, 2009 ▶, 2010 ▶)

Experimental

Crystal data

C10H12ClNO3S

M = 261.72

Triclinic,

a = 8.365 (1) Å

b = 8.719 (1) Å

c = 9.143 (1) Å

α = 92.74 (1)°

β = 104.22 (1)°

γ = 108.75 (1)°

V = 606.24 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.48 mm−1

T = 293 K

0.45 × 0.35 × 0.35 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.814, T max = 0.851

4031 measured reflections

2481 independent reflections

2200 reflections with I > 2σ(I)

R int = 0.011

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.102

S = 1.04

2481 reflections

149 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.27 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/S1600536811004284/ds2091sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004284/ds2091Isup2.hkl

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

C10H12ClNO3S	Z = 2
Mr = 261.72	F(000) = 272
Triclinic, P1	Dx = 1.434 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.365 (1) Å	Cell parameters from 2678 reflections
b = 8.719 (1) Å	θ = 3.0–27.7°
c = 9.143 (1) Å	µ = 0.48 mm−1
α = 92.74 (1)°	T = 293 K
β = 104.22 (1)°	Prism, colourless
γ = 108.75 (1)°	0.45 × 0.35 × 0.35 mm
V = 606.24 (12) Å3

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2481 independent reflections
Radiation source: fine-focus sealed tube	2200 reflections with I > 2σ(I)
graphite	Rint = 0.011
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 3.0°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −10→10
Tmin = 0.814, Tmax = 0.851	k = −10→9
4031 measured reflections	l = −11→11

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)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.102	w = 1/[σ2(Fo2) + (0.0589P)2 + 0.1796P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2481 reflections	Δρmax = 0.39 e Å−3
149 parameters	Δρmin = −0.27 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.074 (7)

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	0.8887 (2)	0.33504 (18)	0.17180 (18)	0.0374 (3)
C2	0.9618 (2)	0.2693 (2)	0.07502 (19)	0.0455 (4)
C3	1.1391 (3)	0.3366 (3)	0.0881 (2)	0.0571 (5)
H3	1.1882	0.2924	0.0234	0.069*
C4	1.2436 (3)	0.4688 (3)	0.1967 (3)	0.0581 (5)
H4	1.3630	0.5137	0.2051	0.070*
C5	1.1725 (3)	0.5347 (2)	0.2926 (2)	0.0546 (5)
H5	1.2436	0.6243	0.3656	0.065*
C6	0.9956 (2)	0.4682 (2)	0.2808 (2)	0.0441 (4)
H6	0.9477	0.5128	0.3462	0.053*
C7	0.7107 (2)	0.0482 (2)	0.36475 (18)	0.0397 (4)
C8	0.6623 (2)	−0.1303 (2)	0.3835 (2)	0.0481 (4)
H8	0.5375	−0.1848	0.3306	0.058*
C9	0.6889 (5)	−0.1514 (4)	0.5501 (3)	0.0922 (9)
H9A	0.6168	−0.1053	0.5915	0.111*
H9B	0.8101	−0.0965	0.6046	0.111*
H9C	0.6566	−0.2657	0.5599	0.111*
C10	0.7668 (3)	−0.2058 (3)	0.3089 (3)	0.0720 (6)
H10A	0.8900	−0.1503	0.3556	0.086*
H10B	0.7401	−0.1958	0.2023	0.086*
H10C	0.7368	−0.3194	0.3215	0.086*
Cl1	0.83725 (8)	0.10188 (7)	−0.06290 (7)	0.0749 (2)
N1	0.63339 (19)	0.07529 (16)	0.22009 (16)	0.0418 (3)
H1N	0.578 (3)	−0.005 (2)	0.150 (2)	0.050*
O1	0.55713 (17)	0.22202 (16)	0.00990 (15)	0.0571 (4)
O2	0.63345 (17)	0.36011 (15)	0.27093 (17)	0.0567 (4)
O3	0.8089 (2)	0.16099 (17)	0.46098 (15)	0.0609 (4)
S1	0.66390 (5)	0.25610 (5)	0.16468 (5)	0.04147 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0413 (8)	0.0280 (7)	0.0386 (8)	0.0104 (6)	0.0055 (6)	0.0046 (6)
C2	0.0544 (10)	0.0359 (8)	0.0409 (8)	0.0119 (7)	0.0098 (7)	−0.0009 (7)
C3	0.0622 (12)	0.0528 (11)	0.0604 (11)	0.0176 (9)	0.0277 (10)	0.0037 (9)
C4	0.0452 (10)	0.0501 (11)	0.0717 (13)	0.0050 (8)	0.0189 (9)	0.0054 (9)
C5	0.0481 (10)	0.0384 (9)	0.0610 (11)	0.0013 (8)	0.0072 (8)	−0.0068 (8)
C6	0.0469 (9)	0.0341 (8)	0.0452 (9)	0.0108 (7)	0.0077 (7)	−0.0024 (7)
C7	0.0393 (8)	0.0378 (8)	0.0400 (8)	0.0126 (7)	0.0090 (7)	0.0020 (6)
C8	0.0424 (9)	0.0400 (9)	0.0549 (10)	0.0088 (7)	0.0070 (8)	0.0130 (8)
C9	0.118 (2)	0.0910 (19)	0.0757 (17)	0.0331 (18)	0.0383 (16)	0.0458 (15)
C10	0.0806 (16)	0.0527 (12)	0.0824 (16)	0.0358 (12)	0.0069 (12)	−0.0016 (11)
Cl1	0.0767 (4)	0.0630 (4)	0.0670 (4)	0.0134 (3)	0.0098 (3)	−0.0306 (3)
N1	0.0444 (8)	0.0286 (7)	0.0412 (7)	0.0055 (6)	0.0017 (6)	0.0008 (5)
O1	0.0500 (7)	0.0446 (7)	0.0586 (8)	0.0094 (6)	−0.0090 (6)	0.0123 (6)
O2	0.0506 (7)	0.0399 (7)	0.0824 (10)	0.0184 (6)	0.0210 (7)	0.0004 (6)
O3	0.0738 (9)	0.0465 (7)	0.0459 (7)	0.0160 (7)	−0.0040 (6)	−0.0078 (6)
S1	0.0381 (2)	0.0302 (2)	0.0493 (3)	0.01005 (16)	0.00256 (17)	0.00424 (17)

C1—C6	1.387 (2)	C7—C8	1.507 (2)
C1—C2	1.389 (2)	C8—C10	1.511 (3)
C1—S1	1.7659 (17)	C8—C9	1.514 (3)
C2—C3	1.380 (3)	C8—H8	0.9800
C2—Cl1	1.7344 (18)	C9—H9A	0.9600
C3—C4	1.377 (3)	C9—H9B	0.9600
C3—H3	0.9300	C9—H9C	0.9600
C4—C5	1.371 (3)	C10—H10A	0.9600
C4—H4	0.9300	C10—H10B	0.9600
C5—C6	1.379 (3)	C10—H10C	0.9600
C5—H5	0.9300	N1—S1	1.6396 (14)
C6—H6	0.9300	N1—H1N	0.843 (15)
C7—O3	1.208 (2)	O1—S1	1.4341 (13)
C7—N1	1.390 (2)	O2—S1	1.4202 (14)
C6—C1—C2	119.32 (16)	C7—C8—H8	108.1
C6—C1—S1	117.57 (13)	C10—C8—H8	108.1
C2—C1—S1	123.11 (13)	C9—C8—H8	108.1
C3—C2—C1	119.91 (16)	C8—C9—H9A	109.5
C3—C2—Cl1	118.08 (14)	C8—C9—H9B	109.5
C1—C2—Cl1	122.01 (14)	H9A—C9—H9B	109.5
C4—C3—C2	120.17 (18)	C8—C9—H9C	109.5
C4—C3—H3	119.9	H9A—C9—H9C	109.5
C2—C3—H3	119.9	H9B—C9—H9C	109.5
C5—C4—C3	120.34 (18)	C8—C10—H10A	109.5
C5—C4—H4	119.8	C8—C10—H10B	109.5
C3—C4—H4	119.8	H10A—C10—H10B	109.5
C4—C5—C6	119.98 (17)	C8—C10—H10C	109.5
C4—C5—H5	120.0	H10A—C10—H10C	109.5
C6—C5—H5	120.0	H10B—C10—H10C	109.5
C5—C6—C1	120.28 (17)	C7—N1—S1	124.59 (11)
C5—C6—H6	119.9	C7—N1—H1N	119.7 (15)
C1—C6—H6	119.9	S1—N1—H1N	115.1 (14)
O3—C7—N1	120.87 (16)	O2—S1—O1	118.79 (9)
O3—C7—C8	125.77 (16)	O2—S1—N1	109.66 (8)
N1—C7—C8	113.34 (14)	O1—S1—N1	104.14 (8)
C7—C8—C10	109.40 (16)	O2—S1—C1	107.71 (8)
C7—C8—C9	110.55 (18)	O1—S1—C1	110.42 (8)
C10—C8—C9	112.5 (2)	N1—S1—C1	105.30 (8)
C6—C1—C2—C3	0.1 (3)	O3—C7—C8—C9	23.2 (3)
S1—C1—C2—C3	−179.39 (15)	N1—C7—C8—C9	−158.19 (19)
C6—C1—C2—Cl1	179.41 (13)	O3—C7—N1—S1	−0.2 (2)
S1—C1—C2—Cl1	0.0 (2)	C8—C7—N1—S1	−178.89 (12)
C1—C2—C3—C4	−0.1 (3)	C7—N1—S1—O2	−51.29 (16)
Cl1—C2—C3—C4	−179.50 (16)	C7—N1—S1—O1	−179.42 (14)
C2—C3—C4—C5	0.0 (3)	C7—N1—S1—C1	64.35 (16)
C3—C4—C5—C6	0.2 (3)	C6—C1—S1—O2	4.95 (16)
C4—C5—C6—C1	−0.3 (3)	C2—C1—S1—O2	−175.59 (14)
C2—C1—C6—C5	0.1 (3)	C6—C1—S1—O1	136.13 (13)
S1—C1—C6—C5	179.61 (14)	C2—C1—S1—O1	−44.41 (16)
O3—C7—C8—C10	−101.1 (2)	C6—C1—S1—N1	−112.02 (14)
N1—C7—C8—C10	77.45 (19)	C2—C1—S1—N1	67.44 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.84 (2)	2.14 (2)	2.976 (2)	174 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.84 (2)	2.14 (2)	2.976 (2)	174 (2)

Symmetry code: (i) .