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Volume 64 
Part 4 
Page o720  
April 2008  

Received 3 March 2008
Accepted 11 March 2008
Online 14 March 2008


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Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.005 Å
R = 0.043
wR = 0.116
Data-to-parameter ratio = 15.7
Details

4-Bromo-2-((E)-{4-[(3,4-dimethylisoxazol-5-yl)sulfamoyl]phenyl}iminiomethyl)phenolate

M. Nawaz Tahir,a Zahid H. Chohan,b Hazoor A. Shadb and Islam Ullah Khanc*

aDepartment of Physics, University of Sargodha, Sargodha, Pakistan,bDepartment of Chemistry, Bahauddin Zakariya University, Multan 60800, Pakistan, and cDepartment of Chemistry, Government College University, Lahore, Pakistan
Correspondence e-mail: dmntahir_uos@yahoo.com

The title compound, C18H16BrN3O4S, is a Schiff base ligand of 5-bromosalicylaldehyde and sulfisoxazole [or N-(3,4-dimethyl-5-isoxazol)sulfanilamide]. The present structure is a zwitterion and is a more precise reinterpretation of the structure which was originally reported by Hämäläinen, Lehtinen & Turpeinen [Arch. Pharm. (1986), 319, 415-420]. The two aromatic rings which make [pi]-[pi] interactions [centroid-centroid distance 3.7538 (18) Å] through intermolecular interactions. There is also a C-Br...[pi] interaction [3.6333 (15) Å] with the heterocyclic ring. An intramolecular N-H...O hydrogen bond also exists. Dimers are formed due to intermolecular N-H...O hydrogen bonding. Intermolecular C-H...O hydrogen bonding links a methyl C atom and the phenolate O atom. The dimers are linked by C-H...N hydrogen bonds, where the C atom is from the Schiff base group and the N atom is of five-membered heterocyclic ring.

Related literature

For related literature, see: Chohan et al. (2008[Chohan, Z. H., Tahir, M. N., Shad, H. A. & Khan, I. U. (2008). Acta Cryst. E64, o648.]); Hämäläinen et al. (1986[Hämäläinen, R., Lehtinen, M. & Turpeinen, U. (1986). Arch. Pharm. 319, 415-420.]); Shad et al. (2008[Shad, H. A., Chohan, Z. H., Tahir, M. N. & Khan, I. U. (2008). Acta Cryst. E64, o635.]).

[Scheme 1]

Experimental

Crystal data

  • C18H16BrN3O4S

  • Mr = 450.31

  • Monoclinic, P 21 /n

  • a = 15.3846 (10) Å

  • b = 7.2235 (5) Å

  • c = 16.5520 (11) Å

  • [beta] = 93.201 (4)°

  • V = 1836.6 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation radiation

  • [mu] = 2.38 mm-1

  • T = 296 (2) K

  • 0.18 × 0.14 × 0.10 mm
Data collection

  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc. Madison, Wisconsion, USA.]) Tmin = 0.685, Tmax = 0.793

  • 18874 measured reflections

  • 3955 independent reflections

  • 2704 reflections with I > 2[sigma](I)

  • Rint = 0.058
Refinement

  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.115

  • S = 1.00

  • 3955 reflections

  • 252 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.46 e Å-3

  • [Delta][rho]min = -0.62 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1 0.80 (3) 1.91 (3) 2.577 (4) 141 (3)
N2-H2...O1i 0.75 (3) 2.09 2.828 (4) 171 (4)
C17-H17C...O1i 0.96 2.58 3.248 (5) 126
C7-H7...N3ii 0.93 2.53 3.420 (4) 161
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc. Madison, Wisconsion, USA.]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc. Madison, Wisconsion, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2069 ).

Acknowledgements

The authors acknowledge the Higher Education Commission, Islamabad, Pakistan, for funding the purchase of the diffractometer.

References

Bruker (2005). SADABS. Bruker AXS Inc. Madison, Wisconsion, USA.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc. Madison, Wisconsion, USA.
Chohan, Z. H., Tahir, M. N., Shad, H. A. & Khan, I. U. (2008). Acta Cryst. E64, o648.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Hämäläinen, R., Lehtinen, M. & Turpeinen, U. (1986). Arch. Pharm. 319, 415-420.
Shad, H. A., Chohan, Z. H., Tahir, M. N. & Khan, I. U. (2008). Acta Cryst. E64, o635.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.

Acta Cryst (2008). E64, o720  [ doi:10.1107/S160053680800682X ]

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