[Journal logo]

Volume 69 
Part 10 
Pages o1558-o1559  
October 2013  

Received 10 September 2013
Accepted 12 September 2013
Online 18 September 2013

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.002 Å
Disorder in main residue
R = 0.051
wR = 0.114
Data-to-parameter ratio = 17.6
Details
Open access

12-(2-Hydroxy-6-oxocyclohex-1-enyl)-9,10-dihydro-8H-benzo[a]xanthen-11(12H)-one

aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,bChemistry and Environmental Division, Manchester Metropolitan University, Manchester, M1 5GD, England, Chemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt,cDepartment of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, Scotland,dChemistry and Environmental Division, Manchester Metropolitan University, Manchester, M1 5GD, UK,eAnalytical Sciences, Manchester Metropolitan University, Manchester, M1 5GD, England, and fDepartment of Chemistry, College of Science, Kirkuk University, Kirkuk, Iraq
Correspondence e-mail: shaabankamel@yahoo.com

In the xanthenone system of the title compound, C23H20O4, the pyran ring has a maximum deviation of 0.111 (1) Å from planarity and the outer cyclohexene ring exhibits a puckered conformation. The three methylene C atoms of the cyclohexene ring bonded to the pyran unit are disordered over two sets of sites [occupancies = 0.570 (3) and 0.430 (3)]. In the crystal, molecules are linked by C-H...O and O-H...O hydrogen bonds, forming a two-dimensional network parallel to (110). A C-H...[pi] interaction occurs between these networks.

Related literature

For related xanthenone structures, see: Li et al. (2004[Li, Y.-L., Wang, X.-S., Shi, D.-Q., Tu, S.-J. & Zhang, Y. (2004). Acta Cryst. E60, o1439-o1441.]); Abdelhamid et al. (2011[Abdelhamid, A. A., Mohamed, S. K., Allahverdiyev, M. A., Gurbanov, A. V. & Ng, S. W. (2011). Acta Cryst. E67, o785.]); Mohamed et al. (2011[Mohamed, S. K., Abdelhamid, A. A., Khalilov, A. N., Gurbanov, A. V. & Ng, S. W. (2011). Acta Cryst. E67, o850-o851.], 2012[Mohamed, S. K., Akkurt, M., Abdelhamid, A. A., Fanwick, P. E. & Potgeiter, H. (2012). Acta Cryst. E68, o1710.]). Reddy et al. (2009[Reddy, B. P., Vijayakumar, V., Narasimhamurthy, T., Suresh, J. & Lakshman, P. L. N. (2009). Acta Cryst. E65, o916.]); Çelik et al. (2009[Çelik, Í., Akkurt, M., Jarrahpour, A., Ebrahimi, E. & Büyükgüngör, O. (2009). Acta Cryst. E65, o2522-o2523.]). For the industrial and pharmaceutical significance of xanthenes, see: Zare et al. (2012[Zare, A., Mokhlesi, M., Hasaninejad, A. & Hekmat-Zadehk, T. (2012). E-J. Chem. 9, 1854-1863.]); Menchen et al. (2003a[Menchen, S. M., Benson, S. C., Lam, J. Y. L., Zhen, W., Sun, D., Rosenblum, B. B., Khan, S. H. & Taing, M. (2003a). US Patent, US 6583168.],b[Menchen, S. M., Benson, S. C., Lam, J. Y. L., Zhen, W., Sun, D., Rosenblum, B. B., Khan, S. H. & Taing, M. (2003b). Chem Abstr. 139, 54287f.]); Sarma & Baruah, (2005[Sarma, R. J. & Baruah, J. B. (2005). Dyes Pigm. 64, 91-92.]). For ring conformations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]) and for standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C23H20O4

  • Mr = 360.41

  • Orthorhombic, P b c a

  • a = 14.2855 (15) Å

  • b = 13.7461 (12) Å

  • c = 18.400 (2) Å

  • V = 3613.2 (6) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 123 K

  • 0.20 × 0.18 × 0.16 mm

Data collection
  • Oxford Diffraction Xcalibur, Eos diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.994, Tmax = 1.000

  • 17944 measured reflections

  • 4541 independent reflections

  • 3366 reflections with I > 2[sigma](I)

  • Rint = 0.042

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.114

  • S = 1.04

  • 4541 reflections

  • 258 parameters

  • 8 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.40 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C2-C7 benzene ring.

D-H...A D-H H...A D...A D-H...A
O3-H3...O4i 0.95 (2) 1.64 (2) 2.5793 (15) 170 (2)
C3-H3A...O3 0.95 2.43 3.367 (2) 168
C9-H9...O2ii 0.95 2.34 3.275 (2) 170
C14-H14B...Cg3iii 0.99 2.85 3.750 (2) 152
Symmetry codes: (i) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]; (ii) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). 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: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and 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: SJ5351 ).


Acknowledgements

AAA thanks the Ministry of Higher Education in Egypt for a grant to support this collaborative project. Manchester Metropolitan University, Erciyes University and University of Strathclyde are gratefully acknowledged for facilitating this study.

References

Abdelhamid, A. A., Mohamed, S. K., Allahverdiyev, M. A., Gurbanov, A. V. & Ng, S. W. (2011). Acta Cryst. E67, o785.  [CSD] [CrossRef] [IUCr Journals]
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Çelik, Í., Akkurt, M., Jarrahpour, A., Ebrahimi, E. & Büyükgüngör, O. (2009). Acta Cryst. E65, o2522-o2523.  [CSD] [CrossRef] [IUCr Journals]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Li, Y.-L., Wang, X.-S., Shi, D.-Q., Tu, S.-J. & Zhang, Y. (2004). Acta Cryst. E60, o1439-o1441.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Menchen, S. M., Benson, S. C., Lam, J. Y. L., Zhen, W., Sun, D., Rosenblum, B. B., Khan, S. H. & Taing, M. (2003a). US Patent, US 6583168.
Menchen, S. M., Benson, S. C., Lam, J. Y. L., Zhen, W., Sun, D., Rosenblum, B. B., Khan, S. H. & Taing, M. (2003b). Chem Abstr. 139, 54287f.
Mohamed, S. K., Abdelhamid, A. A., Khalilov, A. N., Gurbanov, A. V. & Ng, S. W. (2011). Acta Cryst. E67, o850-o851.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Mohamed, S. K., Akkurt, M., Abdelhamid, A. A., Fanwick, P. E. & Potgeiter, H. (2012). Acta Cryst. E68, o1710.  [CSD] [CrossRef] [IUCr Journals]
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Reddy, B. P., Vijayakumar, V., Narasimhamurthy, T., Suresh, J. & Lakshman, P. L. N. (2009). Acta Cryst. E65, o916.  [CSD] [CrossRef] [IUCr Journals]
Sarma, R. J. & Baruah, J. B. (2005). Dyes Pigm. 64, 91-92.  [CSD] [CrossRef] [ChemPort]
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]
Zare, A., Mokhlesi, M., Hasaninejad, A. & Hekmat-Zadehk, T. (2012). E-J. Chem. 9, 1854-1863.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1558-o1559   [ doi:10.1107/S1600536813025324 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.