N-[(4-Chloro-phen-yl)sulfon-yl]acetamide.

The asymmetric unit of the title compound, C(8)H(8)ClNO(3)S, consists of two crystallographically independent mol-ecules (A and B). The dihedral angles between the benzene ring and amide C-C(=O)-NH- plane are 87.6 (3) (mol-ecule A) and 86.0 (3)° (mol-ecule B). In the crystal, the independent mol-ecules are alternately linked by N-H⋯O hydrogen bonds into an infinite chain along the b axis. Short inter-molecular Cl⋯Cl contacts [3.2882 (5) and 3.2812 (5) Å] are also observed.

Related literature

For a related structure, see: Fun et al. (2012 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C8H8ClNO3S

M = 233.66

Monoclinic,

a = 12.1801 (6) Å

b = 9.2529 (4) Å

c = 17.6769 (8) Å

β = 101.979 (1)°

V = 1948.83 (16) Å3

Z = 8

Mo Kα radiation

μ = 0.59 mm−1

T = 100 K

0.36 × 0.14 × 0.14 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.819, T max = 0.923

45479 measured reflections

7130 independent reflections

5439 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.090

S = 1.04

7130 reflections

263 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.48 e Å−3

Δρmin = −0.52 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812033764/is5173sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033764/is5173Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812033764/is5173Isup3.cml

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

C8H8ClNO3S	F(000) = 960
Mr = 233.66	Dx = 1.593 Mg m−3
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 9840 reflections
a = 12.1801 (6) Å	θ = 2.5–32.6°
b = 9.2529 (4) Å	µ = 0.59 mm−1
c = 17.6769 (8) Å	T = 100 K
β = 101.979 (1)°	Block, colourless
V = 1948.83 (16) Å3	0.36 × 0.14 × 0.14 mm
Z = 8

Bruker APEX DUO CCD area-detector diffractometer	7130 independent reflections
Radiation source: fine-focus sealed tube	5439 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
φ and ω scans	θmax = 32.7°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −18→18
Tmin = 0.819, Tmax = 0.923	k = −14→13
45479 measured reflections	l = −26→26

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0436P)2 + 0.5704P] where P = (Fo2 + 2Fc2)/3
7130 reflections	(Δ/σ)max = 0.001
263 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.52 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
Cl1A	0.47973 (2)	0.51064 (3)	0.405269 (18)	0.02673 (7)
S1A	0.170782 (19)	0.51977 (2)	0.076741 (14)	0.01367 (6)
O1A	0.19060 (6)	0.64897 (8)	0.03653 (4)	0.02048 (14)
O2A	0.17384 (6)	0.38233 (8)	0.04030 (4)	0.01910 (14)
O3A	0.03482 (6)	0.33069 (7)	0.15483 (4)	0.01845 (14)
N1A	0.04580 (7)	0.54746 (8)	0.09688 (5)	0.01463 (14)
C1A	0.29561 (8)	0.64713 (10)	0.20474 (6)	0.01909 (18)
H1AA	0.2712	0.7362	0.1802	0.023*
C2A	0.36445 (8)	0.64567 (11)	0.27788 (6)	0.02079 (19)
H2AA	0.3879	0.7335	0.3042	0.025*
C3A	0.39837 (8)	0.51313 (11)	0.31194 (6)	0.01803 (19)
C4A	0.36704 (8)	0.38278 (11)	0.27505 (6)	0.01842 (18)
H4AA	0.3926	0.2939	0.2994	0.022*
C5A	0.29771 (7)	0.38417 (10)	0.20193 (6)	0.01646 (17)
H5AA	0.2745	0.2962	0.1757	0.020*
C6A	0.26276 (8)	0.51635 (9)	0.16772 (6)	0.01437 (17)
C7A	−0.00697 (7)	0.44855 (9)	0.13606 (5)	0.01418 (16)
C8A	−0.11629 (9)	0.49932 (10)	0.15322 (7)	0.01856 (19)
H8AA	−0.1411	0.4314	0.1888	0.028*
H8AB	−0.1729	0.5044	0.1050	0.028*
H8AC	−0.1062	0.5953	0.1771	0.028*
Cl1B	0.52074 (2)	0.97797 (3)	−0.155284 (17)	0.02637 (7)
S1B	0.82941 (2)	1.00993 (2)	0.172976 (15)	0.01367 (6)
O1B	0.80290 (6)	1.13770 (8)	0.21146 (4)	0.01954 (14)
O2B	0.83407 (6)	0.87333 (8)	0.21118 (4)	0.01972 (14)
O3B	0.97057 (6)	0.83316 (7)	0.09436 (4)	0.01887 (14)
N1B	0.95264 (7)	1.04795 (8)	0.15212 (5)	0.01459 (14)
C1B	0.69388 (8)	1.12533 (10)	0.04604 (6)	0.01691 (17)
H1BA	0.7112	1.2157	0.0712	0.020*
C2B	0.62534 (8)	1.11904 (10)	−0.02700 (6)	0.01873 (18)
H2BA	0.5950	1.2048	−0.0526	0.022*
C3B	0.60174 (8)	0.98501 (11)	−0.06205 (6)	0.01785 (18)
C4B	0.64282 (8)	0.85698 (11)	−0.02594 (6)	0.01874 (18)
H4BA	0.6241	0.7667	−0.0508	0.022*
C5B	0.71197 (8)	0.86331 (10)	0.04738 (6)	0.01664 (17)
H5BA	0.7415	0.7773	0.0732	0.020*
C6B	0.73726 (8)	0.99763 (9)	0.08230 (6)	0.01408 (17)
C7B	1.00893 (7)	0.95272 (9)	0.11338 (5)	0.01431 (16)
C8B	1.11652 (8)	1.00994 (10)	0.09647 (7)	0.01848 (19)
H8BA	1.1475	0.9396	0.0651	0.028*
H8BB	1.1704	1.0264	0.1452	0.028*
H8BC	1.1019	1.1012	0.0681	0.028*
H1NB	0.9739 (11)	1.1378 (16)	0.1584 (8)	0.025 (3)*
H1NA	0.0217 (11)	0.6354 (16)	0.0901 (8)	0.026 (3)*

	U11	U22	U33	U12	U13	U23
Cl1A	0.02335 (13)	0.03545 (14)	0.01876 (15)	−0.00052 (9)	−0.00167 (10)	−0.00159 (9)
S1A	0.01605 (11)	0.01243 (10)	0.01325 (12)	0.00092 (7)	0.00468 (8)	0.00067 (7)
O1A	0.0248 (3)	0.0179 (3)	0.0203 (4)	−0.0010 (3)	0.0084 (3)	0.0060 (3)
O2A	0.0240 (3)	0.0163 (3)	0.0169 (3)	0.0032 (2)	0.0043 (3)	−0.0037 (2)
O3A	0.0202 (3)	0.0117 (3)	0.0232 (4)	−0.0001 (2)	0.0038 (3)	0.0033 (2)
N1A	0.0165 (3)	0.0101 (3)	0.0179 (4)	0.0015 (2)	0.0050 (3)	0.0020 (3)
C1A	0.0213 (4)	0.0135 (4)	0.0215 (5)	0.0011 (3)	0.0024 (4)	−0.0019 (3)
C2A	0.0220 (4)	0.0175 (4)	0.0219 (5)	0.0002 (3)	0.0022 (4)	−0.0048 (3)
C3A	0.0146 (4)	0.0225 (4)	0.0165 (5)	−0.0007 (3)	0.0024 (4)	−0.0009 (3)
C4A	0.0175 (4)	0.0177 (4)	0.0196 (5)	−0.0004 (3)	0.0027 (3)	0.0028 (3)
C5A	0.0166 (4)	0.0135 (4)	0.0190 (4)	−0.0004 (3)	0.0029 (3)	0.0010 (3)
C6A	0.0148 (4)	0.0132 (4)	0.0154 (5)	0.0002 (3)	0.0040 (3)	−0.0007 (3)
C7A	0.0156 (4)	0.0129 (4)	0.0137 (4)	−0.0015 (3)	0.0023 (3)	0.0001 (3)
C8A	0.0176 (4)	0.0199 (4)	0.0196 (5)	0.0018 (3)	0.0071 (4)	0.0023 (3)
Cl1B	0.02278 (12)	0.03587 (14)	0.01794 (14)	−0.00114 (9)	−0.00155 (10)	−0.00122 (9)
S1B	0.01612 (11)	0.01213 (9)	0.01342 (12)	−0.00106 (7)	0.00458 (9)	−0.00113 (7)
O1B	0.0222 (3)	0.0182 (3)	0.0193 (4)	0.0006 (2)	0.0067 (3)	−0.0061 (3)
O2B	0.0251 (3)	0.0159 (3)	0.0181 (3)	−0.0030 (2)	0.0044 (3)	0.0039 (2)
O3B	0.0216 (3)	0.0118 (3)	0.0227 (4)	0.0011 (2)	0.0033 (3)	−0.0030 (2)
N1B	0.0169 (3)	0.0099 (3)	0.0179 (4)	−0.0010 (2)	0.0055 (3)	−0.0013 (3)
C1B	0.0198 (4)	0.0125 (4)	0.0187 (4)	−0.0007 (3)	0.0047 (3)	0.0005 (3)
C2B	0.0192 (4)	0.0173 (4)	0.0193 (5)	0.0000 (3)	0.0032 (3)	0.0028 (3)
C3B	0.0143 (4)	0.0227 (4)	0.0162 (5)	−0.0008 (3)	0.0024 (4)	−0.0006 (3)
C4B	0.0174 (4)	0.0177 (4)	0.0203 (5)	−0.0007 (3)	0.0019 (3)	−0.0051 (3)
C5B	0.0167 (4)	0.0127 (4)	0.0200 (5)	0.0001 (3)	0.0027 (3)	−0.0022 (3)
C6B	0.0148 (4)	0.0125 (4)	0.0157 (5)	−0.0008 (3)	0.0048 (4)	−0.0010 (3)
C7B	0.0160 (4)	0.0126 (4)	0.0140 (4)	0.0022 (3)	0.0022 (3)	0.0004 (3)
C8B	0.0172 (4)	0.0192 (4)	0.0204 (5)	−0.0004 (3)	0.0071 (4)	−0.0006 (3)

Cl1A—C3A	1.7394 (11)	Cl1B—C3B	1.7375 (11)
S1A—O2A	1.4295 (7)	S1B—O2B	1.4286 (7)
S1A—O1A	1.4366 (7)	S1B—O1B	1.4339 (7)
S1A—N1A	1.6537 (8)	S1B—N1B	1.6559 (8)
S1A—C6A	1.7591 (11)	S1B—C6B	1.7593 (11)
O3A—C7A	1.2200 (11)	O3B—C7B	1.2206 (11)
N1A—C7A	1.3839 (11)	N1B—C7B	1.3823 (11)
N1A—H1NA	0.865 (14)	N1B—H1NB	0.871 (14)
C1A—C2A	1.3873 (15)	C1B—C2B	1.3855 (14)
C1A—C6A	1.3943 (13)	C1B—C6B	1.3949 (13)
C1A—H1AA	0.9500	C1B—H1BA	0.9500
C2A—C3A	1.3907 (14)	C2B—C3B	1.3895 (14)
C2A—H2AA	0.9500	C2B—H2BA	0.9500
C3A—C4A	1.3864 (14)	C3B—C4B	1.3887 (14)
C4A—C5A	1.3897 (14)	C4B—C5B	1.3925 (14)
C4A—H4AA	0.9500	C4B—H4BA	0.9500
C5A—C6A	1.3913 (13)	C5B—C6B	1.3934 (12)
C5A—H5AA	0.9500	C5B—H5BA	0.9500
C7A—C8A	1.5012 (13)	C7B—C8B	1.4998 (13)
C8A—H8AA	0.9800	C8B—H8BA	0.9800
C8A—H8AB	0.9800	C8B—H8BB	0.9800
C8A—H8AC	0.9800	C8B—H8BC	0.9800
O2A—S1A—O1A	119.64 (5)	O2B—S1B—O1B	119.73 (5)
O2A—S1A—N1A	110.25 (4)	O2B—S1B—N1B	110.14 (4)
O1A—S1A—N1A	103.55 (4)	O1B—S1B—N1B	103.54 (4)
O2A—S1A—C6A	108.95 (4)	O2B—S1B—C6B	109.19 (4)
O1A—S1A—C6A	109.08 (4)	O1B—S1B—C6B	108.77 (4)
N1A—S1A—C6A	104.24 (4)	N1B—S1B—C6B	104.31 (4)
C7A—N1A—S1A	123.31 (6)	C7B—N1B—S1B	122.73 (6)
C7A—N1A—H1NA	120.8 (9)	C7B—N1B—H1NB	120.4 (9)
S1A—N1A—H1NA	114.7 (9)	S1B—N1B—H1NB	115.7 (9)
C2A—C1A—C6A	119.21 (9)	C2B—C1B—C6B	119.35 (9)
C2A—C1A—H1AA	120.4	C2B—C1B—H1BA	120.3
C6A—C1A—H1AA	120.4	C6B—C1B—H1BA	120.3
C1A—C2A—C3A	118.68 (9)	C1B—C2B—C3B	118.81 (9)
C1A—C2A—H2AA	120.7	C1B—C2B—H2BA	120.6
C3A—C2A—H2AA	120.7	C3B—C2B—H2BA	120.6
C4A—C3A—C2A	122.38 (10)	C4B—C3B—C2B	122.34 (10)
C4A—C3A—Cl1A	118.79 (8)	C4B—C3B—Cl1B	118.92 (8)
C2A—C3A—Cl1A	118.81 (8)	C2B—C3B—Cl1B	118.73 (8)
C3A—C4A—C5A	118.96 (9)	C3B—C4B—C5B	118.85 (9)
C3A—C4A—H4AA	120.5	C3B—C4B—H4BA	120.6
C5A—C4A—H4AA	120.5	C5B—C4B—H4BA	120.6
C4A—C5A—C6A	118.98 (9)	C4B—C5B—C6B	119.03 (9)
C4A—C5A—H5AA	120.5	C4B—C5B—H5BA	120.5
C6A—C5A—H5AA	120.5	C6B—C5B—H5BA	120.5
C5A—C6A—C1A	121.79 (9)	C5B—C6B—C1B	121.61 (9)
C5A—C6A—S1A	119.51 (7)	C5B—C6B—S1B	120.13 (7)
C1A—C6A—S1A	118.67 (7)	C1B—C6B—S1B	118.23 (7)
O3A—C7A—N1A	121.09 (8)	O3B—C7B—N1B	120.88 (8)
O3A—C7A—C8A	124.21 (8)	O3B—C7B—C8B	124.43 (8)
N1A—C7A—C8A	114.69 (8)	N1B—C7B—C8B	114.68 (8)
C7A—C8A—H8AA	109.5	C7B—C8B—H8BA	109.5
C7A—C8A—H8AB	109.5	C7B—C8B—H8BB	109.5
H8AA—C8A—H8AB	109.5	H8BA—C8B—H8BB	109.5
C7A—C8A—H8AC	109.5	C7B—C8B—H8BC	109.5
H8AA—C8A—H8AC	109.5	H8BA—C8B—H8BC	109.5
H8AB—C8A—H8AC	109.5	H8BB—C8B—H8BC	109.5
O2A—S1A—N1A—C7A	50.89 (9)	O2B—S1B—N1B—C7B	51.56 (9)
O1A—S1A—N1A—C7A	−179.98 (8)	O1B—S1B—N1B—C7B	−179.27 (8)
C6A—S1A—N1A—C7A	−65.90 (8)	C6B—S1B—N1B—C7B	−65.50 (8)
C6A—C1A—C2A—C3A	−0.07 (15)	C6B—C1B—C2B—C3B	0.04 (14)
C1A—C2A—C3A—C4A	0.83 (16)	C1B—C2B—C3B—C4B	1.14 (16)
C1A—C2A—C3A—Cl1A	−177.29 (8)	C1B—C2B—C3B—Cl1B	−177.27 (7)
C2A—C3A—C4A—C5A	−1.11 (16)	C2B—C3B—C4B—C5B	−1.32 (16)
Cl1A—C3A—C4A—C5A	177.02 (7)	Cl1B—C3B—C4B—C5B	177.08 (8)
C3A—C4A—C5A—C6A	0.60 (15)	C3B—C4B—C5B—C6B	0.32 (15)
C4A—C5A—C6A—C1A	0.14 (15)	C4B—C5B—C6B—C1B	0.83 (15)
C4A—C5A—C6A—S1A	−177.64 (7)	C4B—C5B—C6B—S1B	−177.14 (7)
C2A—C1A—C6A—C5A	−0.41 (15)	C2B—C1B—C6B—C5B	−1.02 (15)
C2A—C1A—C6A—S1A	177.39 (8)	C2B—C1B—C6B—S1B	176.99 (7)
O2A—S1A—C6A—C5A	−18.56 (9)	O2B—S1B—C6B—C5B	−21.27 (9)
O1A—S1A—C6A—C5A	−150.79 (8)	O1B—S1B—C6B—C5B	−153.56 (8)
N1A—S1A—C6A—C5A	99.12 (8)	N1B—S1B—C6B—C5B	96.44 (8)
O2A—S1A—C6A—C1A	163.58 (8)	O2B—S1B—C6B—C1B	160.70 (8)
O1A—S1A—C6A—C1A	31.36 (9)	O1B—S1B—C6B—C1B	28.41 (9)
N1A—S1A—C6A—C1A	−78.73 (8)	N1B—S1B—C6B—C1B	−81.59 (8)
S1A—N1A—C7A—O3A	−3.57 (13)	S1B—N1B—C7B—O3B	−1.87 (13)
S1A—N1A—C7A—C8A	175.90 (7)	S1B—N1B—C7B—C8B	177.08 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N1B—H1NB···O3Ai	0.871 (15)	1.939 (15)	2.7980 (10)	168.6 (13)
N1A—H1NA···O3Bii	0.865 (15)	1.939 (15)	2.7952 (10)	170.0 (13)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1B—H1NB⋯O3A i	0.871 (15)	1.939 (15)	2.7980 (10)	168.6 (13)
N1A—H1NA⋯O3B ii	0.865 (15)	1.939 (15)	2.7952 (10)	170.0 (13)

Symmetry codes: (i) ; (ii) .