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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 [sigma](C-C) = 0.005 Å
R = 0.038
wR = 0.082
Data-to-parameter ratio = 14.0
Details
Open access

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

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-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[Altamura, M., Fedi, V., Giannotti, D., Paoli, P. & Rossi, P. (2009). New J. Chem. 33, 2219-2231.]). For the biological activity of sulfa drugs, see: Chegwidden et al. (2000[Chegwidden, W. R., Carter, N. D. & Edwards, Y. H. (2000). In The Carbonic Anhydrases New Horizons. Basel: Birkhauser Verlag.]); Lu & Tucker (2007[Lu, R. J. & Tucker, J. A. (2007). J. Med. Chem. 50, 6535-6544.]); Tappe et al. (2008[Tappe, W., Zarfl, C., Kummer, S., Burauel, P., Vereecken, H. & Groeneweg, J. (2008). Chemosphere, 72, 836-843.]); Purushottamachar et al. (2008[Purushottamachar, P., Khandelwal, A., Vasaitis, T. S., Bruno, R. D., Gediya, L. K. & Njar, V. C. O. (2008). Bioorg. Med. Chem. 16, 3519-3529.]). For structural studies of molecules having the sulfonamide -SO2-NH group, see: Parkin et al. (2008[Parkin, A., Collins, A., Gilmore, C. J. & Wilson, C. C. (2008). Acta Cryst. B64, 66-71.]); Perlovich et al. (2009[Perlovich, G. L., Tkachev, V. V., Strakhova, N. N., Kazachenko, V. P., Volkova, T. V., Surov, O. V., Schaper, K.-J. & Raevsky, O. A. (2009). J. Pharm. Sci. 98, 4738-4755.], 2011[Perlovich, G. L., Ryzhakov, A. M., Tkachev, T. T. & Hansen, L. K. (2011). Cryst. Growth Des. 11, 1067-1081.]); Vega-Hissi et al. (2011[Vega-Hissi, E. G., Andrada, M. F., Zamarbide, G. N., Estrada, M. R. & Tomas-Vert, F. (2011). J. Mol. Model. 17, 1317-1323.]); Altamura et al. (2009[Altamura, M., Fedi, V., Giannotti, D., Paoli, P. & Rossi, P. (2009). New J. Chem. 33, 2219-2231.], 2012[Altamura, M., Fedi, V., Nannicini, R., Paoli, P. & Rossi, P. (2012). Acta Cryst. E68, o3144-o3145.]).

[Scheme 1]

Experimental

Crystal data
  • C12H10BrClN2O2S

  • Mr = 361.64

  • Monoclinic, P 21 /c

  • a = 13.657 (1) Å

  • b = 14.361 (2) Å

  • c = 7.0829 (9) Å

  • [beta] = 100.75 (1)°

  • V = 1364.8 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.365, Tmax = 0.447

  • 6647 measured reflections

  • 2533 independent reflections

  • 1629 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]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-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)
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[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: PARST (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]).


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

Altamura, M., Fedi, V., Giannotti, D., Paoli, P. & Rossi, P. (2009). New J. Chem. 33, 2219-2231.  [ISI] [CSD] [CrossRef] [ChemPort]
Altamura, M., Fedi, V., Nannicini, R., Paoli, P. & Rossi, P. (2012). Acta Cryst. E68, o3144-o3145.  [CSD] [CrossRef] [details]
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [ISI] [CrossRef] [ChemPort] [details]
Chegwidden, W. R., Carter, N. D. & Edwards, Y. H. (2000). In The Carbonic Anhydrases New Horizons. Basel: Birkhauser Verlag.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Lu, R. J. & Tucker, J. A. (2007). J. Med. Chem. 50, 6535-6544.  [ISI] [CrossRef] [PubMed] [ChemPort]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [details]
Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.
Parkin, A., Collins, A., Gilmore, C. J. & Wilson, C. C. (2008). Acta Cryst. B64, 66-71.  [ISI] [CrossRef] [details]
Perlovich, G. L., Ryzhakov, A. M., Tkachev, T. T. & Hansen, L. K. (2011). Cryst. Growth Des. 11, 1067-1081.  [CrossRef] [ChemPort]
Perlovich, G. L., Tkachev, V. V., Strakhova, N. N., Kazachenko, V. P., Volkova, T. V., Surov, O. V., Schaper, K.-J. & Raevsky, O. A. (2009). J. Pharm. Sci. 98, 4738-4755.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Purushottamachar, P., Khandelwal, A., Vasaitis, T. S., Bruno, R. D., Gediya, L. K. & Njar, V. C. O. (2008). Bioorg. Med. Chem. 16, 3519-3529.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tappe, W., Zarfl, C., Kummer, S., Burauel, P., Vereecken, H. & Groeneweg, J. (2008). Chemosphere, 72, 836-843.  [ISI] [CrossRef] [PubMed] [ChemPort]
Vega-Hissi, E. G., Andrada, M. F., Zamarbide, G. N., Estrada, M. R. & Tomas-Vert, F. (2011). J. Mol. Model. 17, 1317-1323.  [ISI] [ChemPort] [PubMed]


Acta Cryst (2012). E68, o3308-o3309   [ doi:10.1107/S160053681204562X ]

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