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

Altamura, M.; Fedi, V.; Nannicini, R.; Paoli, P.; Rossi, P.

doi:10.1107/S160053681204562X

Volume 68
Part 12
Pages o3308-o3309
December 2012

Received 22 October 2012
Accepted 5 November 2012
Online 10 November 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
R = 0.038
wR = 0.082
Data-to-parameter ratio = 14.0
Details

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

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

^aChemistry Department, Menarini Ricerche S.p.A., Via dei Sette Santi 3, I-50131 Firenze, Italy, and ^bDipartimento Energetica "Sergio Stecco", University of Firenze, Via S. Marta 3, I-50139 Firenze, Italy
Correspondence e-mail: paolapaoli@unifi.it

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-HNH₂ hydrogen bonds. The molecules are further consolidated into layers along the bc plane by weaker N-HO 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, P 2₁ /c
a = 13.657 (1) Å
b = 14.361 (2) Å
c = 7.0829 (9) Å
= 100.75 (1)°
V = 1364.8 (3) Å³
Z = 4
Mo K radiation
= 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 > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.082
S = 0.94
2533 reflections
181 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.32 e Å^-3
_min = -0.38 e Å^-3

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)

Table 2
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-HN1N2ⁱ	0.78 (3)	2.26 (3)	3.022 (4)	166 (3)
N2-HN2AO1ⁱⁱ	0.87 (3)	2.45 (3)	3.258 (4)	154 (3)
Symmetry codes: (i) -x, -y+1, -z+1; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); 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 data and figures for this paper are available from the IUCr electronic archives (Reference: LD2080 ).

Acknowledgements

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

References

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organic compounds