2-Chloro­benzene­sulfonamide

Gowda, B.T.; Foro, S.; Shakuntala, K.; Fuess, H.

doi:10.1107/S1600536809031511

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2144

doi:10.1107/S1600536809031511

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2-Chlorobenzenesulfonamide

B. Thimme Gowda,^a ^* Sabine Foro,^b K. Shakuntala ^a and Hartmut Fuess ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 8 August 2009; accepted 10 August 2009; online 15 August 2009)

In the crystal of the title compound, C₆H₆ClNO₂S, N—H⋯O hydrogen bonds pack the molecules 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_r = 191.63
Monoclinic, C c
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 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) 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[F² > 2σ(F²)] = 0.022
wR(F²) = 0.060
S = 1.03
1031 reflections
106 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ), 215 Friedel pairs
Flack parameter: 0.04 (8)

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) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809031511/bt5028sup1.cif

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

checkCIF report

Comment top

The chemistry of sulfonamides is of interest as they show distinct physical, chemical and biological properties. Many arylsulfonamides and their N-halo compounds exhibit pharmacological, fungicidal and herbicidal activities due to their oxidizing action in aqueous, partial aqueous and non-aqueous media. In the present work, the structure of 2-chlorobenzenesulfonamde has been determined to explore the substituent effects on the solid state structures of sulfonamides and N-halo arylsulfonamides (Gowda et al., 2003; Gowda, Babitha et al. 2007; Gowda, Nayak et al. 2007; Gowda, Srilatha et al. 2007). The structure of the title compound (Fig. 1) closely resembles those of the parent benzenesulfonamide (Gowda, Nayak et al., 2007) and other aryl sulfonamides (Gowda, Babitha et al., 2007; Gowda, Srilatha et al., 2007; Jones & Weinkauf, 1993; Kumar et al., 1992; O'Connor & Maslen, 1965). The title compound crystallizes in monoclinic space group Cc in contrast to the monoclinic Pc space group observed with the parent sulfonamide (Gowda et al., 2007b) and orthorhombic Pbca space group with 4-fluorobenzenesulfonamide (Jones & Weinkauf, 1993) and 4-aminobenzenesulfonamide (O'Connor & Maslen, 1965) and monoclinic P2₁/n space group with 4-chlorobenzenesulfonamide and 4-bromobenzenesulfonamide (Gowda et al., 2003), and 4-methylbenzenesulfonamide (Kumar et al., 1992). The molecules in the title compound are packed into infinite 3-D molecular network through N1—H11···O1 and N1—H12···O2 hydrogen bonding (Table 1 & Fig.2).

Related literature top

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 top

The purity of the commmercial sample (TCI, Tokyo) was checked and characterized by its infrared spectra. The single crystals used in X-ray diffraction studies were grown in ethanol solution by a slow evaporation of the solvent at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of (I), showing the atom labelling scheme and displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.

2-Chlorobenzenesulfonamide top

Crystal data top

C₆H₆ClNO₂S	F(000) = 392
M_r = 191.63	D_x = 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

Data collection top

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 monochromator	R_int = 0.008
Rotation method data acquisition using ω and phi scans.	θ_max = 26.4°, θ_min = 2.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −8→4
T_min = 0.735, T_max = 0.842	k = −18→15
1598 measured reflections	l = −9→9

Refinement top

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(F_o²) + (0.0417P)² + 0.2306P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.041
1031 reflections	Δρ_max = 0.14 e Å⁻³
106 parameters	Δρ_min = −0.21 e Å⁻³
4 restraints	Absolute structure: Flack (1983), 215 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (8)

Crystal data top

C₆H₆ClNO₂S	V = 800.2 (2) Å³
M_r = 191.63	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 6.955 (1) Å	µ = 0.68 mm⁻¹
b = 14.848 (3) Å	T = 299 K
c = 7.751 (1) Å	0.48 × 0.48 × 0.26 mm
β = 91.51 (1)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1031 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	1004 reflections with I > 2σ(I)
T_min = 0.735, T_max = 0.842	R_int = 0.008
1598 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.022	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.060	Δρ_max = 0.14 e Å⁻³
S = 1.03	Δρ_min = −0.21 e Å⁻³
1031 reflections	Absolute structure: Flack (1983), 215 Friedel pairs
106 parameters	Absolute structure parameter: 0.04 (8)
4 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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)

Symmetry codes: (i) x+1/2, −y+1/2, z−1/2; (ii) x−1/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₆H₆ClNO₂S
M_r	191.63
Crystal system, space group	Monoclinic, Cc
Temperature (K)	299
a, b, c (Å)	6.955 (1), 14.848 (3), 7.751 (1)
β (°)	91.51 (1)
V (Å³)	800.2 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.68
Crystal size (mm)	0.48 × 0.48 × 0.26

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.735, 0.842
No. of measured, independent and observed [I > 2σ(I)] reflections	1598, 1031, 1004
R_int	0.008
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.060, 1.03
No. of reflections	1031
No. of parameters	106
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.21
Absolute structure	Flack (1983), 215 Friedel pairs
Absolute structure parameter	0.04 (8)

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) x+1/2, −y+1/2, z−1/2; (ii) x−1/2, −y+1/2, z−1/2.

Acknowledgements

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for an extension of his research fellowship.

References

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