N-(2-Amino-5-chloro­phen­yl)-2-bromo­benzene­sulfonamide

Maria Altamura; Valentina Fedi; Rossano Nannicini; Paola Paoli; Patrizia Rossi

doi:10.1107/S160053681204562X

. 2012 Nov 10;68(Pt 12):o3308–o3309. doi: 10.1107/S160053681204562X

N-(2-Amino-5-chlorophenyl)-2-bromobenzenesulfonamide

Maria Altamura ^a, Valentina Fedi ^a, Rossano Nannicini ^a, Paola Paoli ^b,^*, Patrizia Rossi ^b

PMCID: PMC3588848 PMID: 23468813

Abstract

In the title compound, C₁₂H₁₀BrClN₂O₂S, the sulfonamide group adopts a staggered conformation about the N—S bond [the C—S—N—H torsion angle is 97 (3)°] with the N-atom lone pair bisecting the O=S=O angle. For the C(Ar)—S bond, the ortho-substituted C atom bisects one of O=S–N angles [the C—C—S—N torsion angle is −57.7 (3)°]. The mean planes of the aromatic rings form a dihedral angle of 75.1 (1)°. In the crystal, molecules form inversion dimers through pairs of N—H⋯NH₂ hydrogen bonds. The molecules are further consolidated into layers along the bc plane by weaker N—H⋯O interactions.

Related literature

For the synthesis of the title compound, see: Altamura et al. (2009 ▶). For the biological activity of sulfa drugs, see: Chegwidden et al. (2000 ▶); Lu & Tucker (2007 ▶); Tappe et al. (2008 ▶); Purushottamachar et al. (2008 ▶). For structural studies of molecules having the sulfonamide –SO₂—NH group, see: Parkin et al. (2008 ▶); Perlovich et al. (2009 ▶, 2011 ▶); Vega-Hissi et al. (2011 ▶); Altamura et al. (2009 ▶, 2012 ▶).

Experimental

Crystal data

C₁₂H₁₀BrClN₂O₂S
M _r = 361.64
Monoclinic,
a = 13.657 (1) Å
b = 14.361 (2) Å
c = 7.0829 (9) Å
β = 100.75 (1)°
V = 1364.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 3.36 mm⁻¹
T = 298 K
0.32 × 0.26 × 0.22 mm

Data collection

Oxford Diffraction Xcalibur3 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.365, T _max = 0.447
6647 measured reflections
2533 independent reflections
1629 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.082
S = 0.94
2533 reflections
181 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PARST (Nardelli, 1995 ▶).

Supplementary Material

Click here for additional data file.^{(16.3KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681204562X/ld2080sup1.cif

e-68-o3308-sup1.cif^{(16.3KB, cif)}

Click here for additional data file.^{(121.9KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681204562X/ld2080Isup2.hkl

e-68-o3308-Isup2.hkl^{(121.9KB, hkl)}

Click here for additional data file.^{(4.6KB, cml)}

Supplementary material file. DOI: 10.1107/S160053681204562X/ld2080Isup3.cml

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

Table 1. Selected torsion angles (°).

HN1—N1—S1—C1	97 (3)
HN1—N1—S1—O1	−19 (3)
C7—N1—S1—O2	50.2 (3)
C6—C1—S1—N1	−57.7 (3)
C6—C1—S1—O1	57.8 (3)

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Table 2. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯N2ⁱ	0.78 (3)	2.26 (3)	3.022 (4)	166 (3)
N2—HN2A⋯O1ⁱⁱ	0.87 (3)	2.45 (3)	3.258 (4)	154 (3)

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors acknowledge the CRIST (Centro di Cristallografia Strutturale, University of Firenze), where the data collection was performed.

supplementary crystallographic information

Comment

The study of the structural and conformational properties of the sulfonamide group (R—SO₂—NR₂) is essential to the comprehension of the "sulfa drugs" action. They found applications as HIV inhibitors (Lu & Tucker, 2007), antimicrobial drugs (Tappe et al., 2008), carbonic anhydrase inhibitors (Chegwidden et al., 2000), anti-tumor agents (Purushottamachar et al., 2008), just to name a few. In this respect a lot of publications have appeared reporting structural data of compounds containing the sulfonamide function (Parkin et al., 2008, Altamura et al., 2009, Perlovich et al., 2009, Perlovich et al., 2011,Vega-Hissi et al., 2011, Altamura et al., 2012). The molecule, as expected, has a staggered conformation about the N—S bond, with the N lone pair bisecting the OŜO angle (Table 1, Fig. 1). The value of the dihedral angle C6—C1—S1—O1 (Table 1) is also in the range observed for arylsulfonamides bearing a non-hydrogen atom in ortho position (a bromine atom in this case). The sulfonamide nitrogen atom is almost planar- trigonal (Σ<N=357 (3)°). The aromatic rings are almost perpendicular to each other with a dihedral angle of 75.1 (1)°. In the crystal, dimers are formed by a couple of complementary hydrogen bonds involving the nitrogen atom of the sulfonamide grouping as a donor and amino nitrogen as an acceptor (Table 2). Dimers form layers along bc plane through weaker NH₂···SO₂ H-bonds between the amino group and an oxygen atom of the sulfonamide moiety (Table 2). The remaining amine H atom (HN2B) appears to be involved in bifurcated intra-molecular contacts with the oxygen and the nitrogen atoms of the sulfonamide group (HN2B···O2 = 2.72 (3) Å, N2—HN2B···O2 = 132 (3)°; HN2B···N1 = 2.58 (4) Å, N2—HN2B···N1 = 98 (3)°), which could contribute in stabilization of the observed molecular conformation.

Experimental

For the synthesis of the title compound, see: Altamura et al. (2009). Crystals of the title compound suitable for single-crystal X-ray diffraction analysis were obtained by slow evaporation of an ethyl acetate/hexane solution of N-(2-amino-5-chlorophenyl)-2-bromobenzenesulfonamide.