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Volume 69 
Part 7 
Pages o1091-o1092  
July 2013  

Received 5 June 2013
Accepted 7 June 2013
Online 12 June 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.008 Å
R = 0.068
wR = 0.198
Data-to-parameter ratio = 17.9
Details
Open access

2-[1-(4-Bromophenyl)-3-hydroxy-3-(4-methoxyphenyl)propyl]cyclohexanol

aDepartment of Physics, Faculty of Sciences, Cumhuriyet University, 58140 Sivas, Turkey,bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,cDepartment of Physics, Faculty of Arts and Sciences, Gaziosmanpasa University, 60240 Tokat, Turkey, and dFaculty of Industrial Chemistry and, Environmental Engineering, Politehnica University of Timisoara, 6 Pirvan Boulevard, 300223, Timimisoara, Romania
Correspondence e-mail: akkurt@erciyes.edu.tr

In the title compound, C22H27BrO3, the cyclohexane ring adopts a chair conformation. The dihedral angle between the benzene rings is 41.9 (4)°. In the crystal, molecules are linked by O-H...O and C-H...O hydrogen bonds, forming a three-dimensional network. In addition, [pi]-[pi] stacking interactions [centroid-centroid distance = 3.953 (6) Å] between the benzene rings of the methoxybenzene groups occur.

Related literature

For the biological properties of 1,5-diols, see: Flamme & Roush (2005[Flamme, E. M. & Roush, W. R. (2005). Beilstein J. Org. Chem. 1, 7. doi:10.1186/1860-5397-1-7.]); Hansen et al. (2003[Hansen, T. M., Florence, G. J., Lugo-Mas, P., Chen, J., Abrams, J. N. & Forsyth, C. J. (2003). Tetrahedron Lett. 44, 57-59.]); Huang et al. (2009[Huang, K., Ortiz-Marciales, M., Jesus, M. D. & Stepanenko, V. (2009). J. Heterocycl. Chem. 46, 1252-1258.]); Oger et al. (2010[Oger, C., Marton, Z., Brinkmann, Y., Bultel-Ponce, V., Durand, T., Graber, M. & Galano, J.-M. (2010). J. Org. Chem. 75, 1892-1897.]). For details of the synthesis, see: Ceylan & Gezegen (2008[Ceylan, M. & Gezegen, H. (2008). Turk. J. Chem. 32, 55-61.]); Gezegen et al. (2010[Gezegen, H., Dingil, A. & Ceylan, M. (2010). J. Heterocycl. Chem. 47, 1017-1024.]). For ring conformation analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For standard bond-length data, 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
  • C22H27BrO3

  • Mr = 419.34

  • Monoclinic, C 2/c

  • a = 23.2993 (14) Å

  • b = 10.9282 (5) Å

  • c = 22.3632 (11) Å

  • [beta] = 133.032 (3)°

  • V = 4162.2 (4) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 1.99 mm-1

  • T = 296 K

  • 0.60 × 0.34 × 0.28 mm

Data collection
  • Stoe IPDS 2 diffractometer

  • Absorption correction: integration [X-RED32 (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]) and XABS2 (Parkin et al., 1995[Parkin, S., Moezzi, B. & Hope, H. (1995). J. Appl. Cryst. 28, 53-56.])] Tmin = 0.448, Tmax = 0.572

  • 4301 measured reflections

  • 4301 independent reflections

  • 2327 reflections with I > 2[sigma](I)

  • Rint = 0.000

Refinement
  • R[F2 > 2[sigma](F2)] = 0.068

  • wR(F2) = 0.198

  • S = 1.03

  • 4301 reflections

  • 240 parameters

  • 149 restraints

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

  • [Delta][rho]max = 0.78 e Å-3

  • [Delta][rho]min = -0.56 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1A...O2i 0.82 2.13 2.854 (4) 147
O2-H2A...O2ii 0.78 (3) 2.46 (2) 2.871 (6) 115 (2)
C5-H5...O3iii 0.93 2.36 3.287 (10) 171
Symmetry codes: (i) [-x+{\script{3\over 2}}, -y+{\script{1\over 2}}, -z]; (ii) [-x+2, y, -z+{\script{1\over 2}}]; (iii) x, y-1, z.

Data collection: X-AREA (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); 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: SJ5331 ).


Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayis University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund). The authors are indebted to the Gaziosmanpasa University (grant BAP-2011/94) for financial support of this work.

References

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.
Ceylan, M. & Gezegen, H. (2008). Turk. J. Chem. 32, 55-61.  [ChemPort]
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]
Flamme, E. M. & Roush, W. R. (2005). Beilstein J. Org. Chem. 1, 7. doi:10.1186/1860-5397-1-7.  [CrossRef]
Gezegen, H., Dingil, A. & Ceylan, M. (2010). J. Heterocycl. Chem. 47, 1017-1024.  [CrossRef] [ChemPort]
Hansen, T. M., Florence, G. J., Lugo-Mas, P., Chen, J., Abrams, J. N. & Forsyth, C. J. (2003). Tetrahedron Lett. 44, 57-59.  [Web of Science] [CrossRef] [ChemPort]
Huang, K., Ortiz-Marciales, M., Jesus, M. D. & Stepanenko, V. (2009). J. Heterocycl. Chem. 46, 1252-1258.  [CrossRef] [ChemPort] [PubMed]
Oger, C., Marton, Z., Brinkmann, Y., Bultel-Ponce, V., Durand, T., Graber, M. & Galano, J.-M. (2010). J. Org. Chem. 75, 1892-1897.  [CrossRef] [ChemPort] [PubMed]
Parkin, S., Moezzi, B. & Hope, H. (1995). J. Appl. Cryst. 28, 53-56.  [CrossRef] [ChemPort] [Web of Science] [IUCr Journals]
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]
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.


Acta Cryst (2013). E69, o1091-o1092   [ doi:10.1107/S1600536813015869 ]

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