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

Shakuntala, K.; Fronc, M.; Gowda, B.T.; Kožíšek, J.

doi:10.1107/S1600536811052573

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 (C-C) = 0.004 Å
R = 0.044
wR = 0.128
Data-to-parameter ratio = 11.1
Details

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

K. Shakuntala,^a Marek Fronc,^b B. Thimme Gowda ^a ^* and Jozef Kozísek ^b

^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-HO hydrogen bond. In the crystal, N-HO and O-HO 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); Prasad et al. (2002); Shakuntala et al. (2011), on N-(aryl)-methanesulfonamides, see: Jayalakshmi & Gowda (2004) on N-(aryl)-arylsulfonamides, see: Shetty & Gowda (2005) and on N-chloroarylsulfonamides, see: Gowda & Kumar (2003). For modes of interlinking carboxylic acids by hydrogen bonds, see: Leiserowitz (1976).

Experimental

Crystal data

C₁₀H₇ClN₂O₅·H₂O
M_r = 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 radiation
= 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)] T_min = 0.860, T_max = 0.965
14309 measured reflections
1310 independent reflections
1131 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(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
_max = 0.25 e Å^-3
_min = -0.44 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO11	0.86	2.50	3.178 (3)	136
O2-H7WO1	0.75	1.77	2.515 (3)	171
O11-H11O3ⁱ	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008) and DIAMOND (Brandenburg, 2002); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

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.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Gowda, B. T. & Kumar, B. H. A. (2003). Oxid. Commun. A, 26, 403-425.
Gowda, B. T., Svoboda, I. & Fuess, H. (2000). Z. Naturforsch. Teil A, 55, 779-790.
Jayalakshmi, K. L. & Gowda, B. T. (2004). Z. Naturforsch. Teil A, 59, 491-500.
Leiserowitz, L. (1976). Acta Cryst. B32, 775-802.
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.
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.
Shakuntala, K., Vrábel, V., Gowda, B. T. & Kozísek, J. (2011). Acta Cryst. E67, o3317.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shetty, M. & Gowda, B. T. (2005). Z. Naturforsch. Teil A, 60, 113-120.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds