[Journal logo]

Volume 69 
Part 2 
Page o311  
February 2013  

Received 5 October 2012
Accepted 26 November 2012
Online 31 January 2013

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.003 Å
R = 0.034
wR = 0.093
Data-to-parameter ratio = 14.7
Details
Open access

Methyl 2-bromo-3-(4-chlorobenzenesulfonamido)benzoate

aCollege of Pharmacy, Howard University, 2300 4th Street, NW, Washington, DC 20059, USA, and bDepartment of Chemistry, Howard University, 525 College Street, NW, Washington, DC 20059, USA
Correspondence e-mail: amol.kulkarni@howard.edu

In the crystal structure of the title compound, C14H11BrClNO4S, the molecules form inversion dimers with R22(8) motifs through pairs of N-H...O hydrogen bonds. The benzene rings are not coplanar and subtend a dihedral angle of 66.27 (8)°. The carbomethoxy group makes a dihedral angle of 75.1 (1)° with the ring to which it is attached.

Related literature

Depending on their substitution patterns, sulfonamides display a wide array of biological activity. For their use as antimitotic, antibacterial and anti-obesity agents, see: Hu et al. (2008[Hu, L., Li, Z.-R., Jiang, J.-D. & Boykin, D. W. (2008). Anticancer Agents Med. Chem. 8, 739-745.]); Wydysh et al. (2009[Wydysh, E. A., Medghalchi, S. M., Vadlamudi, A. & Townsend, C. A. (2009). J. Med. Chem. 52, 3317-3327.]). For structures related to the development of novel antimicrobial agents, see: Kulkarni et al. (2012a[Kulkarni, A. A., King, C., Butcher, R. J. & Fortunak, J. M. D. (2012a). Acta Cryst. E68, o1498.],b[Kulkarni, A. A., King, C. L., Fortunak, J. M. D. & Butcher, R. J. (2012b). Acta Cryst. E68, o1497.]).

[Scheme 1]

Experimental

Crystal data
  • C14H11BrClNO4S

  • Mr = 404.66

  • Monoclinic, P 21 /c

  • a = 7.9206 (2) Å

  • b = 9.4600 (3) Å

  • c = 20.0915 (6) Å

  • [beta] = 94.505 (3)°

  • V = 1500.79 (8) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 6.84 mm-1

  • T = 123 K

  • 1.06 × 0.88 × 0.52 mm

Data collection
  • Agilent Xcalibur (Ruby, Gemini) diffractometer

  • Absorption correction: analytical [CrysAlis PRO (Agilent, 2010[Agilent (2010). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]), based on expressions derived by Clark & Reid (1995[Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.])] Tmin = 0.049, Tmax = 0.198

  • 5248 measured reflections

  • 3012 independent reflections

  • 2873 reflections with I > 2[sigma](I)

  • Rint = 0.033

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.093

  • S = 1.08

  • 3012 reflections

  • 205 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.48 e Å-3

  • [Delta][rho]min = -0.65 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O1i 0.80 (4) 2.22 (4) 2.978 (3) 158 (3)
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: CrysAlis PRO (Agilent, 2010[Agilent (2010). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DS2221 ).


Acknowledgements

AAK wishes to acknowledge Dr A. K. Wutoh, Dean of the College of Pharmacy, for the purchase of chemicals and solvents, as well as RCMI, Howard University, and CDRD, College of Pharmacy, Howard University, for their support. RJB wishes to acknowledge the NSF-MRI program (grant CHE-0619278) for funds to purchase the diffractometer.

References

Agilent (2010). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.  [CrossRef] [details]
Hu, L., Li, Z.-R., Jiang, J.-D. & Boykin, D. W. (2008). Anticancer Agents Med. Chem. 8, 739-745.  [CrossRef] [PubMed] [ChemPort]
Kulkarni, A. A., King, C., Butcher, R. J. & Fortunak, J. M. D. (2012a). Acta Cryst. E68, o1498.  [CrossRef] [details]
Kulkarni, A. A., King, C. L., Fortunak, J. M. D. & Butcher, R. J. (2012b). Acta Cryst. E68, o1497.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wydysh, E. A., Medghalchi, S. M., Vadlamudi, A. & Townsend, C. A. (2009). J. Med. Chem. 52, 3317-3327.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o311  [ doi:10.1107/S1600536812048581 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.