electronic reprintActa Crystallographica Section E

Structure ReportsOnline

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2-(2-Iodobenzenesulfonamido)acetic acid

Muhammad Nadeem Arshad, Islam Ullah Khan, Muhammad Shafiq andAzam Mukhtar

Acta Cryst. (2009). E65, o549

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Inorganic compounds

Metal-organic compounds

Organic compounds

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Acta Cryst. (2009). E65, o549 Arshad et al. · C8H8INO4S

2-(2-Iodobenzenesulfonamido)aceticacid

Muhammad Nadeem Arshad,a* Islam Ullah Khan,a

Muhammad Shafiqa and Azam Mukhtarb

aMaterials 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: mnachemist@hotmail.com

Received 24 January 2009; accepted 13 February 2009

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 sulfon-

amide, 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

C8H8INO4SMr = 341.11Triclinic, P1a = 5.5877 (2) Ab = 8.0145 (2) A

c = 12.3584 (4) A� = 80.923 (2)�

� = 83.398 (2)�

� = 88.038 (2)�

V = 542.81 (3) A3

Z = 2Mo K� radiation� = 3.14 mm�1

T = 296 K0.22 � 0.10 � 0.06 mm

Data collection

Bruker Kappa APEXII CCDdiffractometer

Absorption correction: multi-scan(SADABS; Bruker, 2005)Tmin = 0.691, Tmax = 0.834

11492 measured reflections2691 independent reflections2297 reflections with I > 2�(I)Rint = 0.028

Refinement

R[F 2 > 2�(F 2)] = 0.030wR(F 2) = 0.086S = 1.022691 reflections

137 parametersH-atom parameters constrained��max = 1.43 e A�3

��min = �1.09 e A�3

Table 1Hydrogen-bond geometry (A, �).

D—H� � �A D—H H� � �A D� � �A D—H� � �A

N1—H1N� � �O1i 0.86 2.47 3.142 (3) 135O2—H2O� � �O1ii 0.82 1.86 2.676 (4) 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 042-

120607-PS2-183.

Supplementary data and figures for this paper are available from theIUCr 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.

organic compounds

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

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