Methyl 2-(4-acetamido­benzene­sulfon­amido)­benzoate

Khan, I.U.; Sharif, S.; Ali, S.; Ahmad, W.; Tiekink, E.R.T.

doi:10.1107/S1600536811009500

Volume 67
Part 4
Page o903
April 2011

Received 12 March 2011
Accepted 12 March 2011
Online 19 March 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.038
wR = 0.113
Data-to-parameter ratio = 16.0
Details

Methyl 2-(4-acetamidobenzenesulfonamido)benzoate

Islam Ullah Khan,^a ⁺ Shahzad Sharif,^a Salamat Ali,^b Waqar Ahmad ^a and Edward R. T. Tiekink ^c ^*

^aMaterials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore 54000, Pakistan,^bDepartment of Physics, Government College University, Lahore 54000, Pakistan, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: edward.tiekink@gmail.com

The molecule of the title compound, C₁₆H₁₆N₂O₅S, has the shape of the letter V but with a small twist; the dihedral angle formed between the benzene rings is 79.66 (9)°. The presence of an intramolecular N-HO hydrogen bond, leading to an S(6) ring, correlates with the near coplanarity of the carboxylate ester group with the benzene ring to which it is connected. The acetamide residue is slightly twisted out of the plane of its benzene ring [C-C-N-C = 13.1 (3)°]. In the crystal, supramolecular chains along the a axis are mediated by N-HO hydrogen bonds. These are connected into layers via C-HO interactions.

Related literature

For background to the pharmacological uses of sulfonamides, see: Korolkovas (1988); Mandell & Sande (1992). For related structures, see: Sharif et al. (2010); Khan et al. (2010).

Experimental

Crystal data

C₁₆H₁₆N₂O₅S
M_r = 348.37
Triclinic, $[P \overline 1]$
a = 8.2835 (2) Å
b = 9.3722 (3) Å
c = 10.8299 (3) Å
= 85.537 (1)°
= 88.614 (1)°
= 72.203 (1)°
V = 798.11 (4) Å³
Z = 2
Mo K radiation
= 0.23 mm^-1
T = 293 K
0.20 × 0.18 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer
13593 measured reflections
3604 independent reflections
3122 reflections with I > 2(I)
R_int = 0.024

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.113
S = 1.07
3604 reflections
225 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.26 e Å^-3
_min = -0.27 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1nO3	0.86 (1)	1.90 (2)	2.6266 (18)	141 (2)
N2-H2nO2ⁱ	0.86 (2)	2.31 (2)	3.0888 (19)	151 (2)
C10-H10O1ⁱⁱ	0.93	2.57	3.330 (2)	140
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y, -z+2.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5817 ).

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Khan, I. U., Ahmad, W., Sharif, S., Ali, S. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o1218.
Korolkovas, A. (1988). Essentials of Medicinal Chemistry, 2nd ed., pp. 699-716. New York: Wiley.
Mandell, G. L. & Sande, M. A. (1992). In Goodman and Gilman, The Pharmacological Basis of Therapeutics 2, edited by A. Gilman, T. W. Rall, A. S. Nies & P. Taylor, 8th ed., pp. 1047-1057. Singapore: McGraw-Hill.
Sharif, S., Iqbal, H., Khan, I. U., John, P. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o1288.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds