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

The asymmetric unit of the title compound, C(8)H(8)ClNO(3)S, contains two independent mol-ecules in which the C-S-N-C torsion angles are -71.7 (3) and 61.2 (3)°. The benzene rings and the SO(2)-NH-CO-C segments form dihedral angles of 80.2 (1) and 88.1 (2)° in the two independent mol-ecules. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into chains in the b-axis direction.

Related literature

For the sulfanilamide moiety in n class="Chemical">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 study of the effect of substituents on the structures of N-(ar­yl)-amides, see: Gowda et al. (2000 ▶), of N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007 ▶) and of N-(substituted phenyl­sulfon­yl)-substituted amides, see: Gowda et al. (2010 ▶).

Experimental

Crystal data

C8H8ClNO3S

M = 233.66

Monoclinic,

a = 11.215 (2) Å

b = 9.393 (2) Å

c = 19.655 (3) Å

β = 98.61 (2)°

V = 2047.2 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.56 mm−1

T = 293 K

0.16 × 0.16 × 0.04 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis n class="Disease">RED; Oxford Diffraction, 2009 ▶) T min = 0.916, T max = 0.978

8327 measured reflections

4168 independent reflections

1942 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.099

S = 0.95

4168 reflections

261 parameters

2 restraints

H atoms treated by a mixture of independent and n class="Chemical">constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis n class="Disease">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/S1600536811012785/vm2086sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012785/vm2086Isup2.hkl

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

C8H8ClNO3S	F(000) = 960
Mr = 233.66	Dx = 1.516 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1468 reflections
a = 11.215 (2) Å	θ = 2.6–27.9°
b = 9.393 (2) Å	µ = 0.56 mm−1
c = 19.655 (3) Å	T = 293 K
β = 98.61 (2)°	Plate, colourless
V = 2047.2 (6) Å3	0.16 × 0.16 × 0.04 mm
Z = 8

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	4168 independent reflections
Radiation source: fine-focus sealed tube	1942 reflections with I > 2σ(I)
graphite	Rint = 0.048
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −10→14
Tmin = 0.916, Tmax = 0.978	k = −9→11
8327 measured reflections	l = −24→19

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ2(Fo2) + (0.0348P)2] where P = (Fo2 + 2Fc2)/3
4168 reflections	(Δ/σ)max < 0.001
261 parameters	Δρmax = 0.26 e Å−3
2 restraints	Δρmin = −0.26 e Å−3

Experimental. Absorption correction: 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
Cl1	0.51810 (9)	0.17437 (11)	0.37185 (7)	0.0865 (4)
S1	0.27802 (8)	0.36595 (10)	0.38303 (5)	0.0430 (3)
O1	0.19970 (19)	0.4751 (2)	0.39993 (13)	0.0544 (7)
O2	0.27435 (19)	0.2294 (2)	0.41421 (12)	0.0536 (7)
O3	0.2486 (2)	0.5660 (3)	0.26563 (13)	0.0541 (7)
N1	0.2528 (2)	0.3364 (3)	0.29999 (16)	0.0379 (8)
H1N	0.248 (3)	0.249 (2)	0.2887 (17)	0.045*
C1	0.4262 (3)	0.4343 (4)	0.39817 (17)	0.0374 (9)
C2	0.5274 (3)	0.3523 (4)	0.39431 (19)	0.0474 (10)
C3	0.6403 (3)	0.4118 (5)	0.4089 (2)	0.0562 (11)
H3	0.7082	0.3568	0.4057	0.067*
C4	0.6532 (3)	0.5523 (5)	0.4280 (2)	0.0572 (11)
H4	0.7298	0.5916	0.4388	0.069*
C5	0.5534 (4)	0.6345 (4)	0.43133 (19)	0.0549 (11)
H5	0.5623	0.7299	0.4437	0.066*
C6	0.4403 (3)	0.5763 (4)	0.41646 (18)	0.0455 (10)
H6	0.3727	0.6325	0.4187	0.055*
C7	0.2354 (3)	0.4414 (4)	0.2506 (2)	0.0382 (9)
C8	0.1998 (3)	0.3873 (4)	0.17924 (19)	0.0552 (11)
H8A	0.2523	0.3105	0.1709	0.066*
H8B	0.2062	0.4627	0.1470	0.066*
H8C	0.1181	0.3537	0.1738	0.066*
Cl2	0.71788 (9)	0.38447 (10)	0.10127 (6)	0.0742 (4)
S2	0.55209 (8)	0.57945 (11)	0.18903 (6)	0.0530 (3)
O4	0.4912 (2)	0.4460 (3)	0.18511 (14)	0.0686 (8)
O5	0.5000 (2)	0.7009 (3)	0.21600 (15)	0.0696 (8)
O6	0.7597 (2)	0.7639 (3)	0.22798 (14)	0.0606 (8)
N2	0.6830 (3)	0.5457 (3)	0.23640 (17)	0.0460 (8)
H2N	0.693 (3)	0.460 (2)	0.2471 (18)	0.055*
C9	0.5848 (3)	0.6257 (4)	0.10696 (19)	0.0399 (9)
C10	0.6495 (3)	0.5395 (4)	0.0678 (2)	0.0477 (10)
C11	0.6630 (3)	0.5774 (5)	0.0015 (2)	0.0643 (12)
H11	0.7069	0.5194	−0.0241	0.077*
C12	0.6121 (4)	0.6996 (5)	−0.0266 (2)	0.0698 (13)
H12	0.6203	0.7244	−0.0715	0.084*
C13	0.5487 (3)	0.7862 (4)	0.0114 (3)	0.0652 (13)
H13	0.5151	0.8702	−0.0077	0.078*
C14	0.5342 (3)	0.7500 (4)	0.0776 (2)	0.0530 (11)
H14	0.4903	0.8091	0.1026	0.064*
C15	0.7731 (3)	0.6440 (4)	0.2501 (2)	0.0486 (10)
C16	0.8857 (3)	0.5899 (4)	0.2931 (2)	0.0636 (12)
H16A	0.8666	0.5536	0.3358	0.076*
H16B	0.9429	0.6662	0.3021	0.076*
H16C	0.9199	0.5151	0.2688	0.076*

	U11	U22	U33	U12	U13	U23
Cl1	0.0709 (7)	0.0570 (7)	0.1361 (13)	−0.0036 (6)	0.0295 (7)	−0.0294 (8)
S1	0.0420 (5)	0.0432 (6)	0.0434 (7)	−0.0090 (5)	0.0055 (4)	−0.0003 (5)
O1	0.0476 (15)	0.0558 (17)	0.0618 (19)	−0.0011 (12)	0.0151 (12)	−0.0133 (15)
O2	0.0601 (15)	0.0492 (16)	0.051 (2)	−0.0157 (12)	0.0075 (13)	0.0148 (14)
O3	0.0791 (17)	0.0272 (15)	0.054 (2)	−0.0058 (13)	0.0025 (13)	0.0003 (14)
N1	0.0472 (17)	0.0241 (16)	0.039 (2)	−0.0065 (14)	−0.0047 (14)	−0.0022 (17)
C1	0.040 (2)	0.037 (2)	0.034 (2)	−0.0069 (17)	0.0015 (16)	−0.0035 (19)
C2	0.048 (2)	0.049 (2)	0.046 (3)	−0.0083 (19)	0.0077 (18)	−0.005 (2)
C3	0.041 (2)	0.071 (3)	0.057 (3)	−0.004 (2)	0.0120 (18)	−0.002 (3)
C4	0.050 (3)	0.072 (3)	0.048 (3)	−0.028 (2)	0.0022 (19)	0.005 (3)
C5	0.062 (3)	0.053 (3)	0.048 (3)	−0.021 (2)	0.002 (2)	0.003 (2)
C6	0.048 (2)	0.045 (2)	0.042 (3)	−0.0023 (19)	0.0035 (17)	0.005 (2)
C7	0.038 (2)	0.031 (2)	0.045 (3)	−0.0024 (17)	0.0037 (17)	−0.001 (2)
C8	0.073 (3)	0.046 (3)	0.045 (3)	0.004 (2)	0.000 (2)	0.002 (2)
Cl2	0.0904 (8)	0.0504 (7)	0.0851 (10)	0.0276 (6)	0.0237 (6)	−0.0008 (6)
S2	0.0460 (6)	0.0515 (7)	0.0632 (8)	0.0038 (5)	0.0141 (5)	−0.0027 (6)
O4	0.0527 (15)	0.0630 (19)	0.091 (2)	−0.0193 (14)	0.0146 (14)	0.0033 (17)
O5	0.0653 (17)	0.0676 (19)	0.081 (2)	0.0259 (14)	0.0283 (15)	−0.0087 (17)
O6	0.0748 (18)	0.0335 (16)	0.069 (2)	−0.0025 (14)	−0.0023 (14)	−0.0024 (16)
N2	0.0552 (19)	0.0281 (17)	0.054 (2)	0.0019 (16)	0.0048 (16)	0.0010 (18)
C9	0.0354 (19)	0.037 (2)	0.046 (3)	0.0006 (17)	0.0034 (17)	−0.004 (2)
C10	0.047 (2)	0.039 (2)	0.055 (3)	0.0045 (18)	0.001 (2)	−0.003 (2)
C11	0.074 (3)	0.059 (3)	0.060 (4)	0.005 (2)	0.013 (2)	−0.004 (3)
C12	0.091 (3)	0.067 (3)	0.049 (3)	0.000 (3)	0.001 (3)	0.000 (3)
C13	0.069 (3)	0.051 (3)	0.068 (4)	0.006 (2)	−0.014 (3)	0.008 (3)
C14	0.044 (2)	0.046 (3)	0.066 (4)	0.0048 (19)	−0.001 (2)	−0.006 (3)
C15	0.056 (3)	0.039 (2)	0.050 (3)	0.003 (2)	0.005 (2)	−0.008 (2)
C16	0.070 (3)	0.054 (3)	0.061 (3)	0.004 (2)	−0.009 (2)	0.005 (2)

Cl1—C2	1.728 (4)	Cl2—C10	1.729 (4)
S1—O1	1.421 (2)	S2—O5	1.420 (2)
S1—O2	1.425 (2)	S2—O4	1.424 (2)
S1—N1	1.638 (3)	S2—N2	1.647 (3)
S1—C1	1.765 (3)	S2—C9	1.761 (4)
O3—C7	1.210 (4)	O6—C15	1.209 (4)
N1—C7	1.377 (4)	N2—C15	1.366 (4)
N1—H1N	0.850 (17)	N2—H2N	0.835 (17)
C1—C2	1.383 (4)	C9—C14	1.386 (4)
C1—C6	1.384 (4)	C9—C10	1.393 (5)
C2—C3	1.375 (4)	C10—C11	1.382 (5)
C3—C4	1.375 (5)	C11—C12	1.361 (5)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.369 (5)	C12—C13	1.373 (5)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.373 (4)	C13—C14	1.377 (5)
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	C14—H14	0.9300
C7—C8	1.490 (5)	C15—C16	1.499 (4)
C8—H8A	0.9600	C16—H16A	0.9600
C8—H8B	0.9600	C16—H16B	0.9600
C8—H8C	0.9600	C16—H16C	0.9600
O1—S1—O2	119.34 (15)	O5—S2—O4	120.45 (16)
O1—S1—N1	109.54 (15)	O5—S2—N2	108.97 (17)
O2—S1—N1	105.33 (15)	O4—S2—N2	103.94 (16)
O1—S1—C1	107.31 (16)	O5—S2—C9	107.31 (17)
O2—S1—C1	110.00 (15)	O4—S2—C9	109.35 (17)
N1—S1—C1	104.32 (15)	N2—S2—C9	105.95 (16)
C7—N1—S1	124.5 (2)	C15—N2—S2	123.5 (2)
C7—N1—H1N	121 (2)	C15—N2—H2N	123 (2)
S1—N1—H1N	115 (2)	S2—N2—H2N	113 (2)
C2—C1—C6	119.2 (3)	C14—C9—C10	118.3 (4)
C2—C1—S1	123.2 (3)	C14—C9—S2	117.4 (3)
C6—C1—S1	117.5 (3)	C10—C9—S2	124.0 (3)
C3—C2—C1	120.0 (3)	C11—C10—C9	120.7 (3)
C3—C2—Cl1	117.7 (3)	C11—C10—Cl2	118.1 (3)
C1—C2—Cl1	122.3 (3)	C9—C10—Cl2	121.2 (3)
C2—C3—C4	120.2 (4)	C12—C11—C10	120.1 (4)
C2—C3—H3	119.9	C12—C11—H11	120.0
C4—C3—H3	119.9	C10—C11—H11	120.0
C5—C4—C3	120.1 (3)	C11—C12—C13	119.9 (4)
C5—C4—H4	120.0	C11—C12—H12	120.0
C3—C4—H4	120.0	C13—C12—H12	120.0
C4—C5—C6	120.1 (4)	C12—C13—C14	120.8 (4)
C4—C5—H5	120.0	C12—C13—H13	119.6
C6—C5—H5	120.0	C14—C13—H13	119.6
C5—C6—C1	120.4 (3)	C13—C14—C9	120.1 (4)
C5—C6—H6	119.8	C13—C14—H14	119.9
C1—C6—H6	119.8	C9—C14—H14	119.9
O3—C7—N1	121.4 (3)	O6—C15—N2	120.6 (3)
O3—C7—C8	124.4 (4)	O6—C15—C16	124.6 (3)
N1—C7—C8	114.1 (3)	N2—C15—C16	114.7 (3)
C7—C8—H8A	109.5	C15—C16—H16A	109.5
C7—C8—H8B	109.5	C15—C16—H16B	109.5
H8A—C8—H8B	109.5	H16A—C16—H16B	109.5
C7—C8—H8C	109.5	C15—C16—H16C	109.5
H8A—C8—H8C	109.5	H16A—C16—H16C	109.5
H8B—C8—H8C	109.5	H16B—C16—H16C	109.5
O1—S1—N1—C7	42.9 (3)	O5—S2—N2—C15	−54.0 (3)
O2—S1—N1—C7	172.5 (2)	O4—S2—N2—C15	176.4 (3)
C1—S1—N1—C7	−71.7 (3)	C9—S2—N2—C15	61.2 (3)
O1—S1—C1—C2	172.8 (3)	O5—S2—C9—C14	−13.5 (3)
O2—S1—C1—C2	41.5 (3)	O4—S2—C9—C14	118.8 (3)
N1—S1—C1—C2	−71.0 (3)	N2—S2—C9—C14	−129.8 (3)
O1—S1—C1—C6	−5.5 (3)	O5—S2—C9—C10	172.2 (3)
O2—S1—C1—C6	−136.8 (3)	O4—S2—C9—C10	−55.6 (3)
N1—S1—C1—C6	110.7 (3)	N2—S2—C9—C10	55.9 (3)
C6—C1—C2—C3	0.3 (5)	C14—C9—C10—C11	0.2 (5)
S1—C1—C2—C3	−178.0 (3)	S2—C9—C10—C11	174.5 (3)
C6—C1—C2—Cl1	−180.0 (3)	C14—C9—C10—Cl2	178.7 (2)
S1—C1—C2—Cl1	1.8 (5)	S2—C9—C10—Cl2	−6.9 (4)
C1—C2—C3—C4	0.8 (6)	C9—C10—C11—C12	−0.5 (6)
Cl1—C2—C3—C4	−179.0 (3)	Cl2—C10—C11—C12	−179.1 (3)
C2—C3—C4—C5	−1.4 (6)	C10—C11—C12—C13	0.9 (6)
C3—C4—C5—C6	1.0 (6)	C11—C12—C13—C14	−0.9 (6)
C4—C5—C6—C1	0.1 (6)	C12—C13—C14—C9	0.7 (6)
C2—C1—C6—C5	−0.7 (5)	C10—C9—C14—C13	−0.3 (5)
S1—C1—C6—C5	177.7 (3)	S2—C9—C14—C13	−175.0 (3)
S1—N1—C7—O3	6.9 (4)	S2—N2—C15—O6	0.7 (5)
S1—N1—C7—C8	−173.2 (2)	S2—N2—C15—C16	−178.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3i	0.85 (2)	2.03 (2)	2.848 (4)	162 (3)
N2—H2N···O6ii	0.84 (2)	1.96 (2)	2.788 (4)	172 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3i	0.85 (2)	2.03 (2)	2.848 (4)	162 (3)
N2—H2N⋯O6ii	0.84 (2)	1.96 (2)	2.788 (4)	172 (3)

Symmetry codes: (i) ; (ii) .