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Volume 69 
Part 7 
Pages o1125-o1126  
July 2013  

Received 7 June 2013
Accepted 12 June 2013
Online 19 June 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma]() = 0.000 Å
Disorder in main residue
R = 0.056
wR = 0.146
Data-to-parameter ratio = 14.6
Details
Open access

2-Oxo-2H-chromen-4-yl propionate

aLaboratoire de Cristallographie et Physique Moléculaire, UFR SSMT, Université Félix Houphouët Boigny, 22 BP 582 Abidjan 22, Côte d'Ivoire,bLaboratoire de Chimie Bio-organique et Phytochimie, Université de Ouagadougou 03 BP 7021 Ouagadougou 03, Burkina Faso, and cLaboratoire de Physique des Interactions Ioniques et Moléculaire, UMR-CNRS 7345, Equipe "Spectrometrie et Dynamique Moléculaire", Centre Saint Jérôme, Université Aix-Marseille, Case 542 Avenue Escadrille Normandie Niemen F-13397, Marseille Cedex 20, France
Correspondence e-mail: bibilamayayabisseyou@yahoo.fr

In the title compound, C12H10O4, the atoms of the 2-oxo-2H-chromene ring system and the non-H atoms of the 4-substituent all lie on a crystallographic mirror plane. The molecular structure exhibits an intramolecular C-H...O hydrogen bond, which generates an S(6) ring. In the crystal, molecules form R32(12) trimeric units via C-H...O interactions which propagate into layers parallel to the ac plane. These layers are linked by weak C-H...O interactions along the [010] direction, generating a three-dimensional network.

Related literature

For the biological activity of coumarin derivatives, see: Abernethy (1969[Abernethy, J. L. (1969). J. Chem. Educ. 46, 561-568.]); Wang et al. (2001[Wang, M., Wang, L., Li, Y. & Li, Q. (2001). Transition Met. Chem. 26, 307-310.]); Yu et al. (2003[Yu, D., Suzuki, M., Xie, L., Morris-Natschke, S. L. & Lee, K.-H. (2003). Med. Res. Rev. 23, 322-345.], 2007[Yu, D., Morris-Natschke, S. L. & Lee, K.-H. (2007). Med. Res. Rev. 27, 108-132.]); Vukovic et al. (2010[Vukovic, N., Sukdolak, S., Solujic, S. & Niciforovic, N. (2010). Arch. Pharm. Res. 33, 5-15.]). For industrial applications, see: O'Kennedy & Thornes (1997[O'Kennedy, R. & Thornes, R. D. (1997). Coumarins: Biology, Applications and Mode of Action. Wiley & Sons, Chichester.]); Lakshmi et al. (1995[Lakshmi, G. S. P. B., Murthy, Y. L. N., Anjaneyulu, A. S. R. & Santhamma, C. (1995). Dyes and Pigments 29, pp. 211-225.]). For a related structure, see: Abou et al. (2012[Abou, A., Djandé, A., Danger, G., Saba, A. & Kakou-Yao, R. (2012). Acta Cryst. E68, o3438-o3439.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For thermal motion of carbonyl group oxygen atoms, see: Braga & Koetzle (1988[Braga, D. & Koetzle, T. F. (1988). Acta Cryst. B44, 151-156.]).

[Scheme 1]

Experimental

Crystal data
  • C12H10O4

  • Mr = 218.20

  • Orthorhombic, P n m a

  • a = 9.2834 (3) Å

  • b = 6.7081 (2) Å

  • c = 16.8068 (6) Å

  • V = 1046.63 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 298 K

  • 0.40 × 0.40 × 0.20 mm

Data collection
  • Nonius KappaCCD diffractometer

  • 8092 measured reflections

  • 1431 independent reflections

  • 1155 reflections with I > 2[sigma](I)

  • Rint = 0.037

Refinement
  • R[F2 > 2[sigma](F2)] = 0.056

  • wR(F2) = 0.146

  • S = 1.06

  • 1431 reflections

  • 98 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2...O4 0.93 2.21 2.800 (3) 121
C6-H6...O2i 0.93 2.48 3.376 (3) 161
C8-H8...O2ii 0.93 2.71 3.394 (3) 131
Symmetry codes: (i) [x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]; (ii) x+1, y, z.

Data collection: COLLECT (Hooft, 1998[Hooft, R. (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR2004 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]) and WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZQ2203 ).


Acknowledgements

The authors thank the Laboratoire de Physique des Interactions Ioniques et Moléculaires and the Spectropôle of Aix-Marseille Université (France) for the use of their diffractometer.

References

Abernethy, J. L. (1969). J. Chem. Educ. 46, 561-568.  [CrossRef] [ChemPort]
Abou, A., Djandé, A., Danger, G., Saba, A. & Kakou-Yao, R. (2012). Acta Cryst. E68, o3438-o3439.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Braga, D. & Koetzle, T. F. (1988). Acta Cryst. B44, 151-156.  [CrossRef] [Web of Science] [IUCr Journals]
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Hooft, R. (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Lakshmi, G. S. P. B., Murthy, Y. L. N., Anjaneyulu, A. S. R. & Santhamma, C. (1995). Dyes and Pigments 29, pp. 211-225.  [CrossRef] [ChemPort]
O'Kennedy, R. & Thornes, R. D. (1997). Coumarins: Biology, Applications and Mode of Action. Wiley & Sons, Chichester.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Vukovic, N., Sukdolak, S., Solujic, S. & Niciforovic, N. (2010). Arch. Pharm. Res. 33, 5-15.  [CrossRef] [ChemPort] [PubMed]
Wang, M., Wang, L., Li, Y. & Li, Q. (2001). Transition Met. Chem. 26, 307-310.  [Web of Science] [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Yu, D., Morris-Natschke, S. L. & Lee, K.-H. (2007). Med. Res. Rev. 27, 108-132.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Yu, D., Suzuki, M., Xie, L., Morris-Natschke, S. L. & Lee, K.-H. (2003). Med. Res. Rev. 23, 322-345.  [Web of Science] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1125-o1126   [ doi:10.1107/S1600536813016358 ]

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