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Volume 69 
Part 5 
Pages o769-o770  
May 2013  

Received 15 April 2013
Accepted 16 April 2013
Online 20 April 2013

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.007 Å
R = 0.058
wR = 0.134
Data-to-parameter ratio = 15.6
Details
Open access

14-Bromo-12-chloro-2,16-dioxapentacyclo[7.7.5.01,21.03,8.010,15]henicosa-3(8),10,12,14-tetraene-7,20-dione

aDepartment of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, Scotland,bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,cChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England,dChemistry Department, Faculty of Science, Mini University, 61519 El-Minia, Egypt, and ePharmaceutical Chemistry Department, Faculty of Pharmacy, Al Azhar University, Egypt
Correspondence e-mail: shaabankamel@yahoo.com, akkurt@erciyes.edu.tr

In the title compound, C19H16BrClO4, both the fused xanthene rings and one of the cyclohexane rings adopt envelope conformations, while the other cyclohexane ring is in a chair conformation. In the crystal, molecules are linked by C-H...O hydrogen bonds, forming infinite chains running along [10-1] incorporating R22(16) ring motifs. In addition, C-H...[pi] interactions and weak [pi]-[pi] stacking interactions [centroid-centroid distance = 3.768 (3) Å] help to consolidate the packing.

Related literature

For similar structures, see: Mohamed et al. (2012b[Mohamed, S. K., Akkurt, M., Tahir, M. N., Abdelhamid, A. A. & Albayati, M. R. (2012b). Acta Cryst. E68, o2315-o2316.]); Lu et al. (2011[Lu, W., Lian, C., Yang, Y. & Zhu, Y. (2011). Acta Cryst. E67, o2108.]); Abdelhamid et al. (2011[Abdelhamid, A. A., Mohamed, S. K., Allahverdiyev, M. A., Gurbanov, A. V. & Ng, S. W. (2011). Acta Cryst. E67, o785.]). For the bioactiviy of xanthenones, see: Mohamed et al. (2012a[Mohamed, S. K., Abdelhamid, A. A., Maharramov, A. M., Khalilov, A. N., Gurbanov, A. V. & Allahverdiyev, M. A. (2012a). J. Chem. Pharm. Res. 4, 955-965.]); Gobbi et al. (2006[Gobbi, S., Belluti, F., Bisi, A., Piazzi, L., Rampa, A., Zampiron, A., Barbera, M., Caputo, A. & Carrara, M. (2006). Bioorg. Med. Chem. 14, 4101-4109.]); Na (2009[Na, Y. (2009). J. Pharm. Pharmacol. 61, 707-12.]). For ring conformations, see: Cremer and Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C19H16BrClO4

  • Mr = 423.67

  • Monoclinic, P 21 /n

  • a = 10.2741 (6) Å

  • b = 10.2800 (6) Å

  • c = 15.8581 (8) Å

  • [beta] = 102.073 (5)°

  • V = 1637.85 (16) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.70 mm-1

  • T = 123 K

  • 0.25 × 0.20 × 0.18 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 = 0.529, Tmax = 0.616

  • 7243 measured reflections

  • 3516 independent reflections

  • 2547 reflections with I > 2[sigma](I)

  • Rint = 0.042

Refinement
  • R[F2 > 2[sigma](F2)] = 0.058

  • wR(F2) = 0.134

  • S = 1.04

  • 3516 reflections

  • 226 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.79 e Å-3

  • [Delta][rho]min = -0.73 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C1-C6 benzene ring.

D-H...A D-H H...A D...A D-H...A
C8-H8B...O3i 0.99 2.53 3.407 (6) 147
C9-H9B...Cg3ii 0.99 2.89 3.731 (5) 143
Symmetry codes: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -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: HB7072 ).


Acknowledgements

This work was supported financially by the Higher Education Ministry of Egypt. The authors gratefully acknowledge Manchester Metropolitan University, the University of Strathclyde and Erciyes University 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]
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]
Gobbi, S., Belluti, F., Bisi, A., Piazzi, L., Rampa, A., Zampiron, A., Barbera, M., Caputo, A. & Carrara, M. (2006). Bioorg. Med. Chem. 14, 4101-4109.  [CrossRef] [PubMed] [ChemPort]
Lu, W., Lian, C., Yang, Y. & Zhu, Y. (2011). Acta Cryst. E67, o2108.  [CSD] [CrossRef] [details]
Mohamed, S. K., Abdelhamid, A. A., Maharramov, 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., Tahir, M. N., Abdelhamid, A. A. & Albayati, M. R. (2012b). Acta Cryst. E68, o2315-o2316.  [CSD] [CrossRef] [ChemPort] [details]
Na, Y. (2009). J. Pharm. Pharmacol. 61, 707-12.  [CrossRef] [PubMed] [ChemPort]
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o769-o770   [ doi:10.1107/S1600536813010374 ]

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