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Volume 69 
Part 2 
Page o234  
February 2013  

Received 15 December 2012
Accepted 8 January 2013
Online 12 January 2013

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.005 Å
Disorder in main residue
R = 0.040
wR = 0.099
Data-to-parameter ratio = 9.7
Details
Open access

4-Amino-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide-2-nitrobenzoic acid (1/1)

aScience and Engineering Faculty, Queensland University of Technology, GPO Box 2434, Brisbane, Queensland 4001, Australia
Correspondence e-mail: g.smith@qut.edu.au

In the asymmetric unit of the title co-crystal, C12H14N4O2S·C7H5NO4, the sulfamethazine and 2-nitrobenzoic acid molecules form a heterodimer through intermolecular amide-carboxylic acid N-H...O and carboxylic acid-pyrimidine O-H...N hydrogen-bond pairs, giving a cyclic motif [graph set R22(8)]. The dihedral angle between the two aromatic ring systems in the sulfamethazine molecule is 88.96 (18)° and the nitro group of the acid is 50% rotationally disordered. Secondary aniline N-H...Osulfone hydrogen-bonding associations give a two-dimensional structure lying parallel to the ab plane.

Related literature

For background to sulfamethazole as a model for co-crystal formation, see: Caira (2007[Caira, M. R. (2007). Mol. Pharm. 4, 310-316.]); Ghosh et al. (2011[Ghosh, S., Bag, P. P. & Reddy, C. M. (2011). Cryst. Growth Des. 11, 3489-3503.]). For structures of 1:1 adducts of sulfamethazine with nitrobenzoic acid analogues, see: Lynch et al. (2000[Lynch, D. E., Sandhu, P. & Parsons, S. (2000). Aust. J. Chem. 53, 383-387.]); Smith & Wermuth (2012[Smith, G. & Wermuth, U. D. (2012). Acta Cryst. E68, o1649-o1650.]). For graph-set analysis, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]).

[Scheme 1]

Experimental

Crystal data
  • C12H14N4O2S·C7H5NO4

  • Mr = 445.46

  • Orthorhombic, P n a 21

  • a = 14.2945 (4) Å

  • b = 8.0115 (3) Å

  • c = 19.0962 (5) Å

  • V = 2186.91 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.19 mm-1

  • T = 200 K

  • 0.30 × 0.21 × 0.12 mm

Data collection
  • Oxford Diffraction Gemini-S CCD-detector diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]) Tmin = 0.964, Tmax = 0.980

  • 5541 measured reflections

  • 2777 independent reflections

  • 2587 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.099

  • S = 1.04

  • 2777 reflections

  • 286 parameters

  • 29 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 565 Friedel pairs

  • Flack parameter: 0.08 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O12-H12...N1A 0.90 1.77 2.671 (4) 180
N2A-H2A...O11 0.90 2.01 2.862 (4) 158
N41A-H41A...O11Ai 0.92 2.18 2.990 (3) 147
N41A-H42A...O12Aii 0.83 2.24 2.973 (3) 146
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z]; (ii) x, y-1, z.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) within WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GG2106 ).


Acknowledgements

The authors acknowledge financial support from the Australian Reseach Council and the Science and Engineering Faculty and the University Library, Queensland University of Technology.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.
Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.  [CrossRef] [ISI] [details]
Caira, M. R. (2007). Mol. Pharm. 4, 310-316.  [CrossRef] [PubMed] [ChemPort]
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [ISI] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Ghosh, S., Bag, P. P. & Reddy, C. M. (2011). Cryst. Growth Des. 11, 3489-3503.  [CSD] [CrossRef] [ChemPort]
Lynch, D. E., Sandhu, P. & Parsons, S. (2000). Aust. J. Chem. 53, 383-387.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Smith, G. & Wermuth, U. D. (2012). Acta Cryst. E68, o1649-o1650.  [CSD] [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o234  [ doi:10.1107/S1600536813000779 ]

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