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Volume 68 
Part 12 
Pages o3438-o3439  
December 2012  

Received 8 November 2012
Accepted 20 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.004 Å
R = 0.066
wR = 0.163
Data-to-parameter ratio = 13.7
Details
Open access

2-Oxo-2H-chromen-4-yl 4-methoxybenzoate

aLaboratoire de Cristallographie et Physique Moléculaire, UFR SSMT, Université de Cocody, 22 BP 582 Abidjan 22, Côte d'Ivoire,bLaboratoire de Chimie Bio-organique et de Phytochimie, Université de Ouagadougou, 03 BP 7021 Ouagadougou 03, Burkina Faso, and cLaboratoire de Physique des Interactions Ioniques et Moléculaires, Equipe-Spectrométries et Dynamique Moléculaire, Centre Saint Jérôme, Université de Provence, 13397 Marseille, France
Correspondence e-mail: abou_akoun@yahoo.fr

In the title molecule, C17H12O5, the chromen-2-one ring and the 4-methoxybenzoate side chain are inclined to one another at a dihedral angle of 69.82 (9)°. The crystal structure features parallel sheets of centrosymmetric R22(6) dimers joined by a C(7) chain, resulting in centrosymetric tetramers of hydrogen-bonded molecules with graph-set motif R44(40). These centrosymetric tetramers are connected by a pair of hydrogen bonds described by an R22(8) ring motif and a C(7) chain via C-H...O interactions. In the structure, there are also [pi]-[pi] stacking interactions between chromene benzene and the six-membered heterocyclic rings [centroid-centroid distance = 3.691 (2) Å] and weak C=O...[pi] interactions [O...(ring centroid) distance = 3.357 (3) Å].

Related literature

For the biological activity of coumarin derivatives, see: Basanagouda et al. (2009[Basanagouda, M., Kulkarni, M. V., Sharma, D., Gupta, V. K., Sandhyarani, P. & Rasal, V. P. (2009). J. Chem. Sci. 121, 485-495.]); Vukovic et al. (2010[Vukovic, N., Sukdolak, S., Solujic, S. & Niciforovic, N. (2010). Arch. Pharm. Res. 33, 5-15.]); Emmanuel-Giota et al. (2001[Emmanuel-Giota, A. A., Fylaktakidou, K. C., Hadjipavlou-Litina, D. J., Litinas, K. E. & Nicolaides, D. N. (2001). J. Heterocycl. Chem. 38, 717-722.]); Marchenko et al. (2006[Marchenko, M. M., Kopyl'chuk, G. P., Shmarakov, I. A., Ketsa, O. V. & Kushnir, V. M. (2006). Pharm. Chem. J. 40, 296-297.]). 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 [pi]-[pi] stacking interactions, see: Janiak (2000[Janiak, C. (2000). J. Chem. Soc. Dalton Trans. pp. 3885-3896.]).

[Scheme 1]

Experimental

Crystal data
  • C17H12O5

  • Mr = 296.27

  • Triclinic, [P \overline 1]

  • a = 4.371 (1) Å

  • b = 10.535 (4) Å

  • c = 15.193 (2) Å

  • [alpha] = 85.218 (3)°

  • [beta] = 83.688 (2)°

  • [gamma] = 81.893 (1)°

  • V = 686.8 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 298 K

  • 0.25 × 0.15 × 0.04 mm

Data collection
  • Nonius KappaCCD diffractometer

  • 5683 measured reflections

  • 2731 independent reflections

  • 1540 reflections with I > 2[sigma](I)

  • Rint = 0.055

Refinement
  • R[F2 > 2[sigma](F2)] = 0.066

  • wR(F2) = 0.163

  • S = 1.11

  • 2731 reflections

  • 200 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C8-H8...O2i 0.93 2.48 3.407 (4) 173
C2-H2...O4ii 0.93 2.49 3.340 (4) 151
C17-H17B...O5iii 0.96 2.59 3.461 (4) 151
Symmetry codes: (i) -x-1, -y, -z+1; (ii) x+1, y, z; (iii) -x+2, -y-1, -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: SHELXL97, 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: ZS2245 ).


Acknowledgements

The authors thank the Spectropôle Service of the Faculty of Sciences and Techniques of Saint Jérôme (France) for the use of the diffractometer and the NMR spectrometer.

References

Basanagouda, M., Kulkarni, M. V., Sharma, D., Gupta, V. K., Sandhyarani, P. & Rasal, V. P. (2009). J. Chem. Sci. 121, 485-495.  [CSD] [CrossRef] [ChemPort]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
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.  [ISI] [CrossRef] [ChemPort] [details]
Emmanuel-Giota, A. A., Fylaktakidou, K. C., Hadjipavlou-Litina, D. J., Litinas, K. E. & Nicolaides, D. N. (2001). J. Heterocycl. Chem. 38, 717-722.  [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Hooft, R. (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Janiak, C. (2000). J. Chem. Soc. Dalton Trans. pp. 3885-3896.  [CrossRef]
Marchenko, M. M., Kopyl'chuk, G. P., Shmarakov, I. A., Ketsa, O. V. & Kushnir, V. M. (2006). Pharm. Chem. J. 40, 296-297.  [CrossRef] [ChemPort]
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] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Vukovic, N., Sukdolak, S., Solujic, S. & Niciforovic, N. (2010). Arch. Pharm. Res. 33, 5-15.  [CrossRef] [ChemPort] [PubMed]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, o3438-o3439   [ doi:10.1107/S1600536812047666 ]

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