electronic reprint Acta Crystallographica Section E
Structure Reports Online ISSN 1600-5368
Editors: W.T. A. Harrison, J. Simpson and M. Weil
2-(2-Iodobenzenesulfonamido)acetic acid Muhammad Nadeem Arshad, Islam Ullah Khan, Muhammad Shafiq and Azam Mukhtar
Acta Cryst. (2009). E65, o549
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ISSN 1600-5368
Volume 61 Part 11 November 2005
Acta Crystallographica Section E
Structure Reports Online Editors: W. Clegg and D. G. Watson
Inorganic compounds
Metal-organic compounds
Organic compounds
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Crystallography Journals Online is available from journals.iucr.org Acta Cryst. (2009). E65, o549
Arshad et al. · C8 H8 INO4 S
organic compounds Acta Crystallographica Section E
Z=2 Mo K radiation = 3.14 mm1
Structure Reports Online
T = 296 K 0.22 0.10 0.06 mm
ISSN 1600-5368
Data collection
2-(2-Iodobenzenesulfonamido)acetic acid
Bruker Kappa APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005) Tmin = 0.691, Tmax = 0.834
Muhammad Nadeem Arshad,a* Islam Ullah Khan,a Muhammad Shafiqa and Azam Mukhtarb a
Materials Chemistry Laboratory, Department of Chemistry, GC University, Lahore, Pakistan, and bInstitute for Chemical Technology and Analytics, Vienna University of Technology, Vienna, Austria Correspondence e-mail:
[email protected]
˚; Key indicators: single-crystal X-ray study; T = 296 K; mean (C–C) = 0.005 A R factor = 0.030; wR factor = 0.086; data-to-parameter ratio = 19.6.
The title compound, C8H8INO4S, is a halogenated sulfonamide, a medicinally important class of organic compounds. In the crystal structure, intermolecular O—H O hydrogen bonds involving the carboxylic acid groups form characteristic centrosymmetric dimers. These dimers are further linked through centrosymmetric dimeric N—H O interactions involving the amido H atom and a sulfonyl O atom. This leads to the formation of a ribbon-like polymer structure propagating in the b direction.
Related literature For background on sulfonamides, or sulfa drugs, see: Pandya et al. (2003). For the structure of the non-halogenated analogue, see: Arshad et al. (2008b). For the synthesis of the title compound, see: Deng & Mani (2006). For details of related structures: see Arshad et al. (2008a,c). For background on related thiazine heterocycles, see: Arshad et al. (2008d). For standard bond-length data, see: Allen et al. (1987).
Experimental Crystal data
Acta Cryst. (2009). E65, o549
Refinement R[F 2 > 2(F 2)] = 0.030 wR(F 2) = 0.086 S = 1.02 2691 reflections
137 parameters H-atom parameters constrained ˚ 3 max = 1.43 e A ˚ 3 min = 1.09 e A
Table 1
˚ , ). Hydrogen-bond geometry (A
Received 24 January 2009; accepted 13 February 2009
C8H8INO4S Mr = 341.11 Triclinic, P1 ˚ a = 5.5877 (2) A ˚ b = 8.0145 (2) A
11492 measured reflections 2691 independent reflections 2297 reflections with I > 2(I) Rint = 0.028
˚ c = 12.3584 (4) A = 80.923 (2) = 83.398 (2) = 88.038 (2) ˚3 V = 542.81 (3) A
D—H A
D—H
H A
D A
D—H A
N1—H1N O1i O2—H2O O1ii
0.86 0.82
2.47 1.86
3.142 (3) 2.676 (4)
135 176
Symmetry codes: (i) x þ 1; y þ 1; z þ 1; (ii) x þ 1; y þ 2; z þ 1.
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 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON.
MNA acknowledges the Higher Education Commission, Pakistan, for providing a PhD Scholarship under PIN 042120607-PS2-183. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2093).
References Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–S19. Arshad, M. N., Khan, I. U., Ahmad, S., Shafiq, M. & Stoeckli-Evans, H. (2008a). Acta Cryst. E64, m994. Arshad, M. N., Khan, I. U. & Zia-ur-Rehman, M. (2008b). Acta Cryst. E64, o2283–o2284. Arshad, M. N., Tahir, M. N., Khan, I. U., Shafiq, M. & Siddiqui, W. A. (2008c). Acta Cryst. E64, m1628. Arshad, M. N., Tahir, M. N., Khan, I. U., Shafiq, M. & Siddiqui, W. A. (2008d). Acta Cryst. E64, o2045. Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (2007). 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. Pandya, R., Murashima, T., Tedeschi, L. & Barrett, A. G. M. (2003). J. Org. Chem. 68, 8274–8276. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Spek, A. L. (2009). Acta Cryst. D65, 148–155.
doi:10.1107/S1600536809005248
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