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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 Acta Crystallographica Section E

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Acta Cryst. (2009). E65, o549 Arshad et al. · C8 H8 INO4 S
 organic compounds
Acta Crystallographica Section E Z=2 T = 296 K
Structure Reports Mo K radiation 0.22  0.10  0.06 mm
 = 3.14 mm1
Online
ISSN 1600-5368 Data collection
Bruker Kappa APEXII CCD 11492 measured reflections
diffractometer 2691 independent reflections
2-(2-Iodobenzenesulfonamido)acetic Absorption correction: multi-scan 2297 reflections with I > 2
(I)
(SADABS; Bruker, 2005) Rint = 0.028
acid Tmin = 0.691, Tmax = 0.834

Muhammad Nadeem Arshad,a* Islam Ullah Khan,a Refinement

Muhammad Shafiqa and Azam Mukhtarb R[F 2 > 2
(F 2)] = 0.030 137 parameters
wR(F 2) = 0.086 H-atom parameters constrained
a
S = 1.02
max = 1.43 e Å3
Materials Chemistry Laboratory, Department of Chemistry, GC University, Lahore, 2691 reflections
min = 1.09 e Å3
Pakistan, and bInstitute for Chemical Technology and Analytics, Vienna University of
Technology, Vienna, Austria
Correspondence e-mail: mnachemist@hotmail.com
Table 1
Received 24 January 2009; accepted 13 February 2009 Hydrogen-bond geometry (Å,  ).
D—H


A D—H H


A D


A D—H


A
Key indicators: single-crystal X-ray study; T = 296 K; mean
(C–C) = 0.005 Å;
R factor = 0.030; wR factor = 0.086; data-to-parameter ratio = 19.6. N1—H1N


O1i 0.86 2.47 3.142 (3) 135
O2—H2O


O1ii 0.82 1.86 2.676 (4) 176
The title compound, C8H8INO4S, is a halogenated sulfon- Symmetry codes: (i) x þ 1; y þ 1; z þ 1; (ii) x þ 1; y þ 2; z þ 1.
amide, a medicinally important class of organic compounds. In
the crystal structure, intermolecular O—H


O hydrogen Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT
bonds involving the carboxylic acid groups form characteristic (Bruker, 2007); data reduction: SAINT; program(s) used to solve
centrosymmetric dimers. These dimers are further linked structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine
through centrosymmetric dimeric N—H


O interactions structure: SHELXL97 (Sheldrick, 2008); molecular graphics:
involving the amido H atom and a sulfonyl O atom. This ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009);
software used to prepare material for publication: WinGX (Farrugia,
leads to the formation of a ribbon-like polymer structure
1999) and PLATON.
propagating in the b direction.
MNA acknowledges the Higher Education Commission,
Related literature Pakistan, for providing a PhD Scholarship under PIN 042-
For background on sulfonamides, or sulfa drugs, see: Pandya et 120607-PS2-183.
al. (2003). For the structure of the non-halogenated analogue,
see: Arshad et al. (2008b). For the synthesis of the title Supplementary data and figures for this paper are available from the
IUCr electronic archives (Reference: SU2093).
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 References
standard bond-length data, see: Allen et al. (1987). 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,
Experimental USA.
Deng, X. & Mani, N. S. (2006). Green Chem. 8, 835–838.
Crystal data Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.
C8H8INO4S c = 12.3584 (4) Å Pandya, R., Murashima, T., Tedeschi, L. & Barrett, A. G. M. (2003). J. Org.
Mr = 341.11  = 80.923 (2) Chem. 68, 8274–8276.
Triclinic, P1  = 83.398 (2) Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
a = 5.5877 (2) Å  = 88.038 (2) Spek, A. L. (2009). Acta Cryst. D65, 148–155.
b = 8.0145 (2) Å V = 542.81 (3) Å3

Acta Cryst. (2009). E65, o549 doi:10.1107/S1600536809005248 Arshad et al. o549

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