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Volume 69 
Part 2 
Page o284  
February 2013  

Received 17 December 2012
Accepted 26 December 2012
Online 23 January 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.048
wR = 0.170
Data-to-parameter ratio = 11.4
Details
Open access

(Z)-3-(1-Hydroxy-3-oxobut-1-enyl)-6-nitro-2H-chromen-2-one

aCentre for Bioinformatics, School of Life Sciences, Pondicherry University, Puducherry 605 014, India, and bDepartment of Chemistry, Pondicherry University, Puducherry 605 014, India
Correspondence e-mail: krishstrucbio@gmail.com

In the title compound, C13H9NO6, the coumarin system has the benzene ring aligned at 0.61 (18)° with respect to the pyrone ring. An intramolecular O-H...O hydrogen bond stabilizes the molecular conformation and a C-H...O contact also occurs. In the crystal, weak C-H...O interactions link the molecules, forming inversion dimers.

Related literature

For the biological importance of flavinoids and coumarins, see: Murry et al. (1982[Murry, R. D. H., Mendez, J. & Brown, S. A. (1982). In The Natural Coumarins: Occurrence, Chemistry and Biochemistry. New York: John Wiley & Sons.]); Andersen et al. (2006[Andersen, M. & Markham, K. R. (2006). In Flavonoids: Chemistry, Biochemistry and Applications. Boca Raton: CRC Press.]); Murakami et al. (2001[Murakami, A., Yamayoshi, A., Iwase, R., Nishida, J., Yamaoka, T. & Wake, N. (2001). Eur. J. Pharm. Sci. 13, 25-34.]); Wu et al. (2003[Wu, J. Y., Fong, W. F., Zhang, J. X., Leung, C. H., Kwong, H. L. & Yang, M. S. (2003). Eur. J. Pharmacol. 473, 9-17.]). For their use as fluorescent probes and triplet sensitisers, see: Wagner (2009[Wagner, B. D. (2009). Molecules, 14, 210-237.]); Takadate et al. (1995[Takadate, A., Masuda, T., Murata, C., Tanaka, T., Irikura, M. & Goya, S. (1995). Anal. Sci. 11, 97-101.]). For a related structure, see: Da & Quan (2010[Da, Y.-X. & Quan, Z.-J. (2010). Acta Cryst. E66, o2872.]).

[Scheme 1]

Experimental

Crystal data
  • C13H9NO6

  • Mr = 275.21

  • Triclinic, [P \overline 1]

  • a = 7.4591 (13) Å

  • b = 8.2178 (19) Å

  • c = 10.0087 (18) Å

  • [alpha] = 85.202 (17)°

  • [beta] = 77.346 (15)°

  • [gamma] = 89.278 (17)°

  • V = 596.5 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 293 K

  • 0.4 × 0.32 × 0.2 mm

Data collection
  • Oxford Diffraction Xcalibur Eos diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.917, Tmax = 1.000

  • 4789 measured reflections

  • 2093 independent reflections

  • 1395 reflections with I > 2[sigma](I)

  • Rint = 0.033

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.170

  • S = 0.93

  • 2093 reflections

  • 183 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3A...O4 0.82 1.78 2.510 (2) 147
C11-H11...O2 0.93 2.24 2.870 (3) 125
C3-H3...O5i 0.93 2.58 3.308 (3) 136
C7-H7...O4ii 0.93 2.39 3.304 (3) 166
Symmetry codes: (i) -x+2, -y, -z; (ii) x, y-1, z+1.

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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5289 ).


Acknowledgements

RK thanks the Department of Biotechnology and the Department of Information Technology, Government of India, New Delhi, for their financial support of the Centre for Bioinformatics, Pondicherry University, Puducherry. NST [No. F. 14-2(ST)/2010 (SA-III)] thanks the UGC for a Rajiv Gandhi National Fellowship to pursue his PhD degree. HSPR and VT thank the Council for Scientific and Industrial Research (CSIR), New Delhi, for financial support.

References

Andersen, M. & Markham, K. R. (2006). In Flavonoids: Chemistry, Biochemistry and Applications. Boca Raton: CRC Press.
Da, Y.-X. & Quan, Z.-J. (2010). Acta Cryst. E66, o2872.  [CSD] [CrossRef] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Murakami, A., Yamayoshi, A., Iwase, R., Nishida, J., Yamaoka, T. & Wake, N. (2001). Eur. J. Pharm. Sci. 13, 25-34.  [ISI] [CrossRef] [PubMed] [ChemPort]
Murry, R. D. H., Mendez, J. & Brown, S. A. (1982). In The Natural Coumarins: Occurrence, Chemistry and Biochemistry. New York: John Wiley & Sons.
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Takadate, A., Masuda, T., Murata, C., Tanaka, T., Irikura, M. & Goya, S. (1995). Anal. Sci. 11, 97-101.  [CrossRef] [ChemPort]
Wagner, B. D. (2009). Molecules, 14, 210-237.  [CrossRef] [PubMed] [ChemPort]
Wu, J. Y., Fong, W. F., Zhang, J. X., Leung, C. H., Kwong, H. L. & Yang, M. S. (2003). Eur. J. Pharmacol. 473, 9-17.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o284  [ doi:10.1107/S1600536812051872 ]

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