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Volume 69 
Part 4 
Pages o616-o617  
April 2013  

Received 22 February 2013
Accepted 22 March 2013
Online 28 March 2013

Key indicators
Single-crystal X-ray study
T = 130 K
Mean [sigma](C-C) = 0.003 Å
R = 0.043
wR = 0.111
Data-to-parameter ratio = 9.1
Details
Open access

9-(2-Hydroxy-6-oxocyclohex-1-en-1-yl)-2,3,4,9-tetrahydro-1H-xanthen-1-one

aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England,bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,cDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and dDepartment Chemie, Fakultät für Naturwissenschaften, Universität Paderborn, Warburgerstrasse 100, D-33098 Paderborn, Germany
Correspondence e-mail: shaabankamel@yahoo.com_and_akkurt@erciyes.edu.tr

In the xanthene ring system in the title compound, C19H18O4, the 4H-pyran ring has a maximum deviation of 0.110 (2) Å from planarity and the cyclohexene ring exhibits a puckered conformation [puckering parameters QT = 0.452 (3) Å, [theta] = 57.0 (4) and [varphi] = 131.7 (4)°]. The cyclohexene ring attached to the xanthene system adopts an envelope conformation, with the middle of the three methylene C atoms as the flap atom. In the crystal, O-H...O and C-H...O hydrogen bonds form infinite chains of R12(6) ring motifs along [100] with the xanthene groups arranged in an alternating zigzag manner.

Related literature

For the bioactivity of xanthene compounds, see: Mohamed et al. (2012a[Mohamed, S. K., Abdelhamid, A. A., Moharramov, A. M., Khalilov, A. N., Gurbanov, A. V. & Allahverdiyev, M. A. (2012a). J. Chem. Pharm. Res. 4, 955-965.]); Mo et al. (2010[Mo, Y., Zang, H.-J. & Cheng, B.-W. (2010). Acta Cryst. E66, o2129.]) and for their fluorescence properties, see: Menchen et al. (2003[Menchen, S. M., Benson, S. C., Lam, J. Y. L., Zhen, W., Sun, D., Rosenblum, B. B., Khan, S. H. & Taing, M. U. S. (2003). US Patent 6 583 168.]). For similar structures see: 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.], 2012b[Mohamed, S. K., Akkurt, M., Abdelhamid, A. A., Fanwick, P. E. & Potgeiter, H. (2012b). Acta Cryst. E68, o1710.]); Kurbanova et al. (2012[Kurbanova, M. M., Gurbanov, A. V., Mahmudov, K. T., Maharramov, A. M. & Ng, S. W. (2012). Acta Cryst. E68, o1606.]); Abdelhamid et al. (2011[Abdelhamid, A. A., Mohamed, S. K., Allahverdiyev, M. A., Gurbanov, A. V. & Ng, S. W. (2011). Acta Cryst. E67, o785.]); Reddy et al. (2009[Reddy, B. P., Vijayakumar, V., Narasimhamurthy, T., Suresh, J. & Lakshman, P. L. N. (2009). Acta Cryst. E65, o916.]). For ring conformations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). 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.]).

[Scheme 1]

Experimental

Crystal data
  • C19H18O4

  • Mr = 310.33

  • Orthorhombic, P n a 21

  • a = 13.4420 (18) Å

  • b = 8.0015 (10) Å

  • c = 14.2416 (18) Å

  • V = 1531.8 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 130 K

  • 0.37 × 0.24 × 0.15 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.966, Tmax = 0.986

  • 13880 measured reflections

  • 1901 independent reflections

  • 1799 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.111

  • S = 1.06

  • 1901 reflections

  • 209 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.39 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2...O1i 0.84 1.76 2.582 (2) 164
C5-H5A...O1i 0.99 2.42 3.034 (3) 119
Symmetry code: (i) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z].

Data collection: SMART (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NK2202 ).


Acknowledgements

Manchester Metropolitan University, Universität Paderborn, Erciyes University and Quaid-I-Azam University are gratefully acknowledged for supporting 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] [details]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Kurbanova, M. M., Gurbanov, A. V., Mahmudov, K. T., Maharramov, A. M. & Ng, S. W. (2012). Acta Cryst. E68, o1606.  [CrossRef] [details]
Menchen, S. M., Benson, S. C., Lam, J. Y. L., Zhen, W., Sun, D., Rosenblum, B. B., Khan, S. H. & Taing, M. U. S. (2003). US Patent 6 583 168.
Mo, Y., Zang, H.-J. & Cheng, B.-W. (2010). Acta Cryst. E66, o2129.  [CSD] [CrossRef] [details]
Mohamed, S. K., Abdelhamid, A. A., Khalilov, A. N., Gurbanov, A. V. & Ng, S. W. (2011). Acta Cryst. E67, o850-o851.  [CSD] [CrossRef] [details]
Mohamed, S. K., Abdelhamid, A. A., Moharramov, A. M., Khalilov, A. N., Gurbanov, A. V. & Allahverdiyev, M. A. (2012a). J. Chem. Pharm. Res. 4, 955-965.  [ChemPort]
Mohamed, S. K., Akkurt, M., Abdelhamid, A. A., Fanwick, P. E. & Potgeiter, H. (2012b). Acta Cryst. E68, o1710.  [CrossRef] [details]
Reddy, B. P., Vijayakumar, V., Narasimhamurthy, T., Suresh, J. & Lakshman, P. L. N. (2009). Acta Cryst. E65, o916.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o616-o617   [ doi:10.1107/S1600536813007952 ]

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