2-Chloro-benzene-sulfonamide.

In the crystal of the title compound, C(6)H(6)ClNO(2)S, N-H⋯O hydrogen bonds pack the mol-ecules into sheets parallel to the ac plane.

Related literature

For our studies of the effect of substituents on the solid state structures of sulfonamides and N-halo aryl­sulfonamides, see: Gowda et al. (2003 ▶); Gowda, Babitha et al. (2007 ▶); Gowda, Nayak et al. (2007 ▶); Gowda, Srilatha et al. (2007 ▶). For the parent benzene­sulfonamide, see: Gowda, Nayak et al. (2007 ▶). For other aryl sulfonamides, see: Gowda, Babitha et al. (2007 ▶); Gowda, Srilatha et al. (2007 ▶); Jones & Weinkauf (1993 ▶); Kumar et al. (1992 ▶); O’Connor & Maslen (1965 ▶).

Experimental

Crystal data

C6H6ClNO2S

M = 191.63

Monoclinic,

a = 6.955 (1) Å

b = 14.848 (3) Å

c = 7.751 (1) Å

β = 91.51 (1)°

V = 800.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.68 mm−1

T = 299 K

0.48 × 0.48 × 0.26 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.735, T max = 0.842

1598 measured reflections

1031 independent reflections

1004 reflections with I > 2σ(I)

R int = 0.008

Refinement

R[F 2 > 2σ(F 2)] = 0.022

wR(F 2) = 0.060

S = 1.03

1031 reflections

106 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), 215 Friedel pairs

Flack parameter: 0.04 (8)

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/S1600536809031511/bt5028sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809031511/bt5028Isup2.hkl

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

C6H6ClNO2S	F(000) = 392
Mr = 191.63	Dx = 1.591 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1188 reflections
a = 6.955 (1) Å	θ = 2.6–27.8°
b = 14.848 (3) Å	µ = 0.68 mm−1
c = 7.751 (1) Å	T = 299 K
β = 91.51 (1)°	Prism, colourless
V = 800.2 (2) Å3	0.48 × 0.48 × 0.26 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1031 independent reflections
Radiation source: fine-focus sealed tube	1004 reflections with I > 2σ(I)
graphite	Rint = 0.008
Rotation method data acquisition using ω and phi scans.	θmax = 26.4°, θmin = 2.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −8→4
Tmin = 0.735, Tmax = 0.842	k = −18→15
1598 measured reflections	l = −9→9

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)] = 0.022	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.060	w = 1/[σ2(Fo2) + (0.0417P)2 + 0.2306P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.041
1031 reflections	Δρmax = 0.14 e Å−3
106 parameters	Δρmin = −0.21 e Å−3
4 restraints	Absolute structure: Flack (1983), 215 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.04 (8)

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
Cl1	0.56409 (10)	0.10747 (7)	0.84733 (11)	0.0700 (3)
S1	0.18379 (8)	0.20974 (3)	0.98884 (8)	0.03276 (14)
O1	−0.0067 (3)	0.22742 (12)	1.0448 (3)	0.0486 (5)
O2	0.3434 (3)	0.23916 (13)	1.0939 (2)	0.0535 (5)
N1	0.2010 (4)	0.25747 (15)	0.8048 (3)	0.0396 (5)
H11	0.309 (3)	0.251 (2)	0.755 (4)	0.048*
H12	0.105 (4)	0.249 (2)	0.740 (3)	0.048*
C1	0.1995 (4)	0.09052 (15)	0.9649 (3)	0.0335 (5)
C2	0.3626 (4)	0.04740 (18)	0.9082 (4)	0.0443 (6)
C3	0.3663 (6)	−0.0459 (2)	0.8966 (4)	0.0588 (8)
H3	0.4755	−0.0751	0.8582	0.071*
C4	0.2078 (7)	−0.0951 (2)	0.9421 (4)	0.0674 (10)
H4	0.2106	−0.1576	0.9341	0.081*
C5	0.0464 (6)	−0.05329 (19)	0.9990 (4)	0.0590 (8)
H5	−0.0600	−0.0872	1.0292	0.071*
C6	0.0415 (4)	0.04025 (18)	1.0117 (4)	0.0432 (6)
H6	−0.0677	0.0689	1.0515	0.052*

	U11	U22	U33	U12	U13	U23
Cl1	0.0380 (4)	0.0856 (6)	0.0871 (6)	0.0153 (4)	0.0158 (4)	0.0148 (5)
S1	0.0338 (3)	0.0335 (2)	0.0310 (2)	−0.0015 (3)	0.00213 (18)	−0.0023 (2)
O1	0.0468 (11)	0.0480 (9)	0.0520 (11)	0.0068 (9)	0.0205 (9)	−0.0043 (9)
O2	0.0590 (14)	0.0501 (11)	0.0506 (11)	−0.0152 (10)	−0.0172 (10)	−0.0031 (9)
N1	0.0364 (11)	0.0449 (11)	0.0375 (11)	0.0035 (10)	0.0025 (8)	0.0055 (9)
C1	0.0381 (12)	0.0343 (10)	0.0280 (11)	0.0023 (11)	−0.0025 (9)	0.0013 (8)
C2	0.0478 (16)	0.0476 (13)	0.0374 (13)	0.0118 (13)	−0.0008 (12)	0.0047 (11)
C3	0.078 (2)	0.0498 (15)	0.0485 (15)	0.0276 (17)	−0.0026 (15)	0.0016 (13)
C4	0.116 (3)	0.0360 (14)	0.0497 (18)	0.0069 (19)	−0.0055 (19)	0.0025 (12)
C5	0.079 (2)	0.0399 (14)	0.0574 (18)	−0.0158 (15)	−0.0058 (17)	0.0052 (13)
C6	0.0445 (16)	0.0412 (12)	0.0436 (14)	−0.0049 (12)	−0.0026 (12)	0.0022 (11)

Cl1—C2	1.737 (3)	C2—C3	1.389 (4)
S1—O1	1.429 (2)	C3—C4	1.376 (5)
S1—O2	1.4275 (19)	C3—H3	0.9300
S1—N1	1.600 (2)	C4—C5	1.366 (5)
S1—C1	1.784 (2)	C4—H4	0.9300
N1—H11	0.857 (19)	C5—C6	1.393 (4)
N1—H12	0.835 (18)	C5—H5	0.9300
C1—C6	1.385 (4)	C6—H6	0.9300
C1—C2	1.384 (4)
O1—S1—O2	118.92 (13)	C3—C2—Cl1	118.6 (2)
O1—S1—N1	106.32 (13)	C4—C3—C2	119.8 (3)
O2—S1—N1	107.32 (12)	C4—C3—H3	120.1
O1—S1—C1	105.88 (12)	C2—C3—H3	120.1
O2—S1—C1	108.31 (12)	C5—C4—C3	120.8 (3)
N1—S1—C1	109.91 (11)	C5—C4—H4	119.6
S1—N1—H11	116 (2)	C3—C4—H4	119.6
S1—N1—H12	113 (2)	C4—C5—C6	119.8 (3)
H11—N1—H12	114 (3)	C4—C5—H5	120.1
C6—C1—C2	119.8 (2)	C6—C5—H5	120.1
C6—C1—S1	117.2 (2)	C1—C6—C5	119.9 (3)
C2—C1—S1	123.0 (2)	C1—C6—H6	120.1
C1—C2—C3	119.9 (3)	C5—C6—H6	120.1
C1—C2—Cl1	121.5 (2)
O1—S1—C1—C6	−3.7 (2)	S1—C1—C2—Cl1	−2.5 (3)
O2—S1—C1—C6	124.8 (2)	C1—C2—C3—C4	−0.2 (4)
N1—S1—C1—C6	−118.19 (19)	Cl1—C2—C3—C4	−179.3 (2)
O1—S1—C1—C2	178.5 (2)	C2—C3—C4—C5	−0.1 (4)
O2—S1—C1—C2	−52.9 (2)	C3—C4—C5—C6	−0.1 (5)
N1—S1—C1—C2	64.0 (2)	C2—C1—C6—C5	−1.0 (4)
C6—C1—C2—C3	0.7 (4)	S1—C1—C6—C5	−178.8 (2)
S1—C1—C2—C3	178.4 (2)	C4—C5—C6—C1	0.7 (4)
C6—C1—C2—Cl1	179.77 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···O1i	0.86 (2)	2.12 (2)	2.908 (3)	152 (3)
N1—H12···O2ii	0.84 (2)	2.12 (2)	2.941 (3)	166 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H11⋯O1i	0.857 (19)	2.12 (2)	2.908 (3)	152 (3)
N1—H12⋯O2ii	0.835 (18)	2.12 (2)	2.941 (3)	166 (3)

Symmetry codes: (i) ; (ii) .