Received 2 April 2013
In the title compound, C26H22ClFO2, the cyclopropane ring is disordered over two orientations, with site-occupancy factors of 0.64 (2) and 0.36 (2). The major occupancy component of the cyclopropane ring makes dihedral angles of 47.6 (7), 50.4 (7) and 65.4 (7)° with the fluoro-, chloro- and unsubstituted benzene rings, respectively [the corresponding values for the minor occupancy component are 47.6 (12), 51.0 (12) and 60.9 (12)°]. An intramolecular C-HO hydrogen bond occurs. The F and Cl atoms deviate by 0.0508 (12) and 0.0592 (7) Å from the planes of their attached benzene rings. In the crystal, C-HF hydrogen bonds link the molecules into chains along the b-axis direction.
Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2628 ).
The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. TS and DV thank the UGC (SAP-CAS) for the departmental facilties. TS also thanks the DST Inspire program for financial assistance.
Bennett, I., Broom, N. J. P., Cassels, R., Elder, J. S., Masson, N. D. & O'Hanlon, P. J. (1999). Bioorg. Med. Chem. Lett. 9, 1847-1852.
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Li, K.-Z., Chen, Y.-T., Zhao, C.-W., Wei, G.-D. & He, Q.-P. (2008). Acta Cryst. E64, o1665.
Sato, K., Yamazoe, S., Yamamoto, R., Ohata, S., Tarui, A., Omote, M., Kumadaki, I. & Ando, A. (2008). Org. Lett. 10, 2405-2408.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.