(2S)-3-(1H-Indol-3-yl)-2-(4-methyl­benzene­sulfonamido)­propionic acid monohydrate

Khan, I.U.; Arshad, M.N.; Mubashar-ur-Rehman, H.; Harrison, W.T.A.; Ali, M.B.

doi:10.1107/S1600536811032089

Volume 67
Part 9
Page o2325
September 2011

Received 4 August 2011
Accepted 8 August 2011
Online 11 August 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.006 Å
R = 0.055
wR = 0.107
Data-to-parameter ratio = 18.4
Details

(2S)-3-(1H-Indol-3-yl)-2-(4-methylbenzenesulfonamido)propionic acid monohydrate

Islam Ullah Khan,^a Muhammad Nadeem Arshad,^a ^* Hafiz Mubashar-ur-Rehman,^a William T. A. Harrison ^b and Muhammad Baqir Ali ^a

^aMaterials Chemistry Laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan, and ^bDepartment of Chemistry, University of Aberdeen, Aberdeen, AB24 3UE, Scotland
Correspondence e-mail: mnachemist@hotmail.com, iukhan.gcu@gmail.com

In the title compound, C₁₈H₁₈N₂O₄S·H₂O, the indole and toluene ring systems are oriented at a dihedral angle of 84.51 (9)°. In the crystal, the components are linked by N-HO, O-HO, C-HO and N-H [pi] interactions. These include a short link from the [alpha] -C atom of the amino acid fragment.

Related literature

For details of the synthesis, see: Deng & Mani (2006). For background to sulfonamides in biology, see: Parka et al. (2009); Wang et al. (2007). For related structures, see: Li et al. (2008); Khan et al. (2011).

Experimental

Crystal data

C₁₈H₁₈N₂O₄S·H₂O
M_r = 376.42
Monoclinic, P 2₁
a = 8.4531 (10) Å
b = 5.2521 (5) Å
c = 20.867 (2) Å
= 98.056 (4)°
V = 917.30 (17) Å³
Z = 2
Mo K radiation
= 0.21 mm^-1
T = 296 K
0.28 × 0.11 × 0.09 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007) T_min = 0.944, T_max = 0.982
10939 measured reflections
4475 independent reflections
2135 reflections with I > 2(I)
R_int = 0.064

Refinement

R[F² > 2(F²)] = 0.055
wR(F²) = 0.107
S = 0.94
4475 reflections
243 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.20 e Å^-3
_min = -0.25 e Å^-3
Absolute structure: Flack (1983), 1951 Friedel pairs
Flack parameter: -0.05 (10)

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C12-C17 ring.

D-HA	D-H	HA	DA	D-HA
N1-H1NO2ⁱ	0.88 (4)	2.37 (4)	3.208 (4)	160 (3)
N2-H2NCg3ⁱⁱ	0.79 (4)	2.85 (4)	3.480 (4)	139 (4)
O3-H3OO5ⁱⁱⁱ	0.82	1.81	2.629 (4)	177
C7-H7O4^iv	0.98	2.37	3.205 (4)	143
C18-H18CO1^v	0.96	2.59	3.456 (5)	151
O5-H1WO2ⁱ	0.89	2.05	2.935 (4)	174
Symmetry codes: (i) x, y+1, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (iii) x-1, y, z; (iv) x, y-1, z; (v) $[-x+1, y-{\script{1\over 2}}, -z]$ .

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 PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WN2443 ).

Acknowledgements

The authors acknowledge the Higher Education Commission of Pakistan for providing a grant to strengthen the Materials Chemistry Laboratory at GC University, Lahore, Pakistan.

References

Bruker (2007). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Deng, X. & Mani, N. S. (2006). Green Chem. 8, 835-838.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Khan, M. H., Khan, I. U., Arshad, M. N., Rafique, H. M. & Harrison, W. T. A. (2011). Crystals, 1, 69-77.
Li, W. M., Wang, J. G., Gau, W. C., Li, Z. M. & Song, H. B. (2008). Chin. J. Struct. Chem. 27, 691-696.
Parka, K., Gopalsamya, A., Aplascaa, A., Ellingboea, J. W., Xub, W., Zhangc, Y. & Levina, J. I. (2009). Bioorg. Med. Chem. 17, 3857-3865.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Wang, J. G., Xiao, Y. J., Li, Y. H., Ma, Y. & Li, Z. M. (2007). Bioorg. Med. Chem. 15, 374-380.

organic compounds