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

Ghafoor, A.Z.; Chang, B.; King, C.L.; Butcher, R.J.; Kulkarni, A.A.

doi:10.1107/S1600536812048581

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 (C-C) = 0.003 Å
R = 0.034
wR = 0.093
Data-to-parameter ratio = 14.7
Details

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

Ahmad Z. Ghafoor,^a Brian Chang,^a Christopher L. King,^b Ray J. Butcher ^b and Amol A. Kulkarni ^a ^*

^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-HO 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); Wydysh et al. (2009). For structures related to the development of novel antimicrobial agents, see: Kulkarni et al. (2012a,b).

Experimental

Crystal data

C₁₄H₁₁BrClNO₄S
M_r = 404.66
Monoclinic, P 2₁ /c
a = 7.9206 (2) Å
b = 9.4600 (3) Å
c = 20.0915 (6) Å
= 94.505 (3)°
V = 1500.79 (8) Å³
Z = 4
Cu K radiation
= 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), based on expressions derived by Clark & Reid (1995)] T_min = 0.049, T_max = 0.198
5248 measured reflections
3012 independent reflections
2873 reflections with I > 2(I)
R_int = 0.033

Refinement

R[F² > 2(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
_max = 0.48 e Å^-3
_min = -0.65 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO1ⁱ	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); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); 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.
Hu, L., Li, Z.-R., Jiang, J.-D. & Boykin, D. W. (2008). Anticancer Agents Med. Chem. 8, 739-745.
Kulkarni, A. A., King, C., Butcher, R. J. & Fortunak, J. M. D. (2012a). Acta Cryst. E68, o1498.
Kulkarni, A. A., King, C. L., Fortunak, J. M. D. & Butcher, R. J. (2012b). Acta Cryst. E68, o1497.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wydysh, E. A., Medghalchi, S. M., Vadlamudi, A. & Townsend, C. A. (2009). J. Med. Chem. 52, 3317-3327.

organic compounds