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Volume 68 
Part 1 
Page o3  
January 2012  

Received 22 November 2011
Accepted 27 November 2011
Online 3 December 2011

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.002 Å
R = 0.057
wR = 0.150
Data-to-parameter ratio = 17.1
Details
Open access

4-[(Hydroxy)(4-methylphenyl)methylidene]isochroman-1,3-dione

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 Phytochimie, Université de Ouagadougou 03 BP 7021 Ouagadougou 03, Burkina Faso, and cUniversité de Provence, Laboratoire de Spectrométrie et Dynamique Moléculaire, case 542 Avenue Escadrille Normandie Niemen, F-13397 Marseille, Cedex 20, France.
Correspondence e-mail: abou_akoun@yahoo.fr

In the title compound, C17H12O4, the six-membered heterocyclic ring adopts a distorted screw-boat conformation. The molecular structure exhibits an S(6) ring motif, owing to an intramolecular O-H...O hydrogen bond. In the crystal, weak C-H...O contacts generate an infinite chain along the c axis. There are also [pi]-[pi] stacking interactions between neighbouring isochromanedione benzene rings, with a centroid-centroid distance of 3.755 (1) Å, and C-O...[pi] interactions with an O...centroid distance of 3.964 (2) Å.

Related literature

For the biological activity of isochromanones, see: Bianchi et al., (2004[Bianchi, D. A., Blanco, N. E., Carrillo, N. & Kaufnam, T. S. (2004). J. Agric. Food Chem. 52, 1923-1927.]); Buntin et al. (2008[Buntin, K., Rachid, S., Scharfe, M., Blöcker, H., Weissman, K. J. & Müller, R. (2008). Angew. Chem. Int. Ed. Engl. 47, 4595-4599.]). For [pi]-[pi] stacking interactions, see: Janiak (2000[Janiak, C. (2000). J. Chem. Soc. Dalton Trans. pp. 3885-3896.]). 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 ring puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C17H12O4

  • Mr = 280.27

  • Monoclinic, P 21 /c

  • a = 15.6767 (6) Å

  • b = 5.9655 (2) Å

  • c = 14.4589 (4) Å

  • [beta] = 102.961 (1)°

  • V = 1317.74 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 298 K

  • 0.40 × 0.34 × 0.10 mm

Data collection
  • Nonius KappaCCD diffractometer

  • 12419 measured reflections

  • 3304 independent reflections

  • 2684 reflections with I > 2[sigma](I)

  • Rint = 0.053

Refinement
  • R[F2 > 2[sigma](F2)] = 0.057

  • wR(F2) = 0.150

  • S = 1.08

  • 3304 reflections

  • 193 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 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
O4-H4...O3 0.82 1.75 2.485 (2) 148
C7-H7...O2i 0.93 2.57 3.299 (2) 136
Symmetry code: (i) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

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, 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: FJ2488 ).


Acknowledgements

We thank the Laboratoire de Physique des Interactions Ioniques et Spectropôle, Université de Provence, and Université Paul Cézanne, Faculté des Sciences et Techniques de Saint Jérôme, Marseille, France, for the use of their diffractometer.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bianchi, D. A., Blanco, N. E., Carrillo, N. & Kaufnam, T. S. (2004). J. Agric. Food Chem. 52, 1923-1927.  [ISI] [CrossRef] [PubMed] [ChemPort]
Buntin, K., Rachid, S., Scharfe, M., Blöcker, H., Weissman, K. J. & Müller, R. (2008). Angew. Chem. Int. Ed. Engl. 47, 4595-4599.  [CrossRef] [PubMed] [ChemPort]
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]
Cremer, D. & Pople, J. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Hooft, R. (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Janiak, C. (2000). J. Chem. Soc. Dalton Trans. pp. 3885-3896.  [CrossRef]
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]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, o3  [ doi:10.1107/S1600536811050975 ]

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