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Volume 68 
Part 1 
Pages o99-o100  
January 2012  

Received 3 December 2011
Accepted 6 December 2011
Online 14 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.044
wR = 0.128
Data-to-parameter ratio = 11.1
Details
Open access

N-(2-Chloro-4-nitrophenyl)maleamic acid monohydrate

aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and bInstitute of Physical Chemistry and Chemical Physics, Slovak University of Technology, Radlinského 9, SK-812 37 Bratislava, Slovak Republic
Correspondence e-mail: gowdabt@yahoo.com

The title compound, C10H7ClN2O5·H2O, crystallizes with a half-molecule each of N-(2-chloro-4-nitrophenyl)maleamic acid (located on a mirror plane) and water (located on a twofold rotation axis) in the asymmetric unit. The main molecule is planar by symmetry and its conformation is stabilized by an intramolecular O-H...O hydrogen bond. In the crystal, N-H...O and O-H...O hydrogen bonds link the molecules into a three-dimensional network.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda et al. (2000[Gowda, B. T., Svoboda, I. & Fuess, H. (2000). Z. Naturforsch. Teil A, 55, 779-790.]); Prasad et al. (2002[Prasad, S. M., Sinha, R. B. P., Mandal, D. K. & Rani, A. (2002). Acta Cryst. E58, o1296-o1297.]); Shakuntala et al. (2011[Shakuntala, K., Vrábel, V., Gowda, B. T. & Kozísek, J. (2011). Acta Cryst. E67, o3317.]), on N-(aryl)-methanesulfonamides, see: Jayalakshmi & Gowda (2004[Jayalakshmi, K. L. & Gowda, B. T. (2004). Z. Naturforsch. Teil A, 59, 491-500.]) on N-(aryl)-arylsulfonamides, see: Shetty & Gowda (2005[Shetty, M. & Gowda, B. T. (2005). Z. Naturforsch. Teil A, 60, 113-120.]) and on N-chloroarylsulfonamides, see: Gowda & Kumar (2003[Gowda, B. T. & Kumar, B. H. A. (2003). Oxid. Commun. A, 26, 403-425.]). For modes of interlinking carboxylic acids by hydrogen bonds, see: Leiserowitz (1976[Leiserowitz, L. (1976). Acta Cryst. B32, 775-802.]).

[Scheme 1]

Experimental

Crystal data
  • C10H7ClN2O5·H2O

  • Mr = 288.64

  • Orthorhombic, C m c a

  • a = 6.7499 (2) Å

  • b = 20.3357 (5) Å

  • c = 17.1671 (4) Å

  • V = 2356.42 (11) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.35 mm-1

  • T = 293 K

  • 0.81 × 0.25 × 0.12 mm

Data collection
  • Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector

  • Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]), based on expressions derived by Clark & Reid (1995[Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.])] Tmin = 0.860, Tmax = 0.965

  • 14309 measured reflections

  • 1310 independent reflections

  • 1131 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.128

  • S = 1.07

  • 1310 reflections

  • 118 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.44 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O11 0.86 2.50 3.178 (3) 136
O2-H7W...O1 0.75 1.77 2.515 (3) 171
O11-H11...O3i 1.05 (1) 2.04 (2) 2.978 (2) 146 (3)
Symmetry code: (i) [-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z].

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]) and DIAMOND (Brandenburg, 2002[Brandenburg, K. (2002). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5742 ).


Acknowledgements

MF and JK thank the VEGA Grant Agency of the Slovak Ministry of Education (1/0679/11) and the Research and Development Agency of Slovakia (APVV-0202-10) for financial support and the Structural Funds, Interreg IIIA, for financial support in purchasing the diffractometer. KS thanks the University Grants Commission, Government of India, New Delhi, for award of a research fellowship under its faculty improvement program.

References

Brandenburg, K. (2002). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Gowda, B. T. & Kumar, B. H. A. (2003). Oxid. Commun. A, 26, 403-425.  [ChemPort]
Gowda, B. T., Svoboda, I. & Fuess, H. (2000). Z. Naturforsch. Teil A, 55, 779-790.  [ChemPort]
Jayalakshmi, K. L. & Gowda, B. T. (2004). Z. Naturforsch. Teil A, 59, 491-500.  [ChemPort]
Leiserowitz, L. (1976). Acta Cryst. B32, 775-802.  [CrossRef] [details]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Prasad, S. M., Sinha, R. B. P., Mandal, D. K. & Rani, A. (2002). Acta Cryst. E58, o1296-o1297.  [CSD] [CrossRef] [details]
Shakuntala, K., Vrábel, V., Gowda, B. T. & Kozísek, J. (2011). Acta Cryst. E67, o3317.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shetty, M. & Gowda, B. T. (2005). Z. Naturforsch. Teil A, 60, 113-120.  [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o99-o100   [ doi:10.1107/S1600536811052573 ]

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