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Volume 70 
Part 1 
Page o76  
January 2014  

Received 10 December 2013
Accepted 13 December 2013
Online 21 December 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.068
wR = 0.273
Data-to-parameter ratio = 11.4
Details
Open access

(4-Fluoro­phen­yl)(4-hy­droxy-3-methyl­phen­yl)methanone

aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India, and bDepartment of Chemistry, Yuvaraja's College, University of Mysore, Mysore 570 005, India
Correspondence e-mail: mas@physics.uni-mysore.ac.in

In the title compound, C14H11FO2, the two benzene rings are not coplanar, with a dihedral angle of 57.45 (12)° between their planes. In the crystal, mol­ecules are linked by an O-H...O hydrogen bond, forming a 21 helical chain along the b axis.

Related literature

For the biological activities of benzo­phenone derivatives, see: Khanum et al. (2004[Khanum, S. A., Venu, T. D., Shashikanth, S. & Firdouse, A. (2004). Bioorg. Med. Chem. Lett. 12, 2093-2095.]); Naveen et al. (2006[Naveen, S., Khanum, S. A., Devaiah, V. T., Shashikanth, S., Anandalwar, S. M. & Prasad, S. (2006). Anal. Sci. 22, 183-184.]); Selvi et al. (2003[Selvi, A. T., Joseph, G. S. & Jayaprakasha, G. K. (2003). Food Microbiol. 20, 455-460.]). For related structures, see: Mahendra et al. (2005[Mahendra, M., Khanum, S. A., Singh, A. K., Shashikanth, S., Doreswamy, B. H., Sridhar, M. A. & Shashidhara Prasad, J. (2005). Acta Cryst. E61, o2990-o2991.]); Dileep, Lakshmi Ranganatha et al. (2013[Dileep, C. S., Lakshmi Ranganatha, V., Lokanath, N. K., Shaukath, A. K. & Sridhar, M. A. (2013). Acta Cryst. E69, o1550.]); Dileep, Prashanth et al. (2013[Dileep, C. S., Prashanth, T., Jeyaseelan, S., Khanum, S. A. & Sridhar, M. A. (2013). Acta Cryst. E69, o1676.]). For 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
  • C14H11FO2

  • Mr = 230.23

  • Monoclinic, P 21 /n

  • a = 5.9265 (10) Å

  • b = 13.112 (2) Å

  • c = 14.556 (2) Å

  • [beta] = 96.875 (7)°

  • V = 1123.0 (3) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.85 mm-1

  • T = 296 K

  • 0.27 × 0.25 × 0.23 mm

Data collection
  • Bruker X8 Proteum diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.804, Tmax = 0.829

  • 7047 measured reflections

  • 1769 independent reflections

  • 1317 reflections with I > 2[sigma](I)

  • Rint = 0.065

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

  • wR(F2) = 0.273

  • S = 1.16

  • 1769 reflections

  • 155 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.36 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O14-H14...O9i 0.82 1.91 2.688 (3) 158
Symmetry code: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. 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: Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5325 ).


Acknowledgements

The authors would like to thank the University of Mysore for providing the diffractometer facility under IoE. CSD would like to thank the University of Mysore for awarding an RFSMS fellowship under the head DV5/Physics/389/RFSMS/2009-2010/10.07.2012. VLR acknowledges the financial support provided by the Department of Science and Technology, New Delhi, under the INSPIRE-Fellowship scheme [IF110555]. SAK gratefully acknowledges the financial assistance provided by UGC under major research project scheme [F.39/737/2010 (SR)].

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.  [CrossRef]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Dileep, C. S., Lakshmi Ranganatha, V., Lokanath, N. K., Shaukath, A. K. & Sridhar, M. A. (2013). Acta Cryst. E69, o1550.  [CSD] [CrossRef] [IUCr Journals]
Dileep, C. S., Prashanth, T., Jeyaseelan, S., Khanum, S. A. & Sridhar, M. A. (2013). Acta Cryst. E69, o1676.  [CSD] [CrossRef] [IUCr Journals]
Khanum, S. A., Venu, T. D., Shashikanth, S. & Firdouse, A. (2004). Bioorg. Med. Chem. Lett. 12, 2093-2095.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Mahendra, M., Khanum, S. A., Singh, A. K., Shashikanth, S., Doreswamy, B. H., Sridhar, M. A. & Shashidhara Prasad, J. (2005). Acta Cryst. E61, o2990-o2991.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Naveen, S., Khanum, S. A., Devaiah, V. T., Shashikanth, S., Anandalwar, S. M. & Prasad, S. (2006). Anal. Sci. 22, 183-184.  [PubMed]
Selvi, A. T., Joseph, G. S. & Jayaprakasha, G. K. (2003). Food Microbiol. 20, 455-460.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2014). E70, o76  [ doi:10.1107/S1600536813033783 ]

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