Received 30 December 2012
In the title compound, C21H13ClO, the central anthracene system is distorted towards a boat conformation and the outer rings are not coplanar with the central ring [dihedral angles = 7.79 (1) and 11.90 (1)°]. The crystal structure features inversion dimers with graph-set motif R22(18) formed by C-HO interactions.
For ring conformations, see: Cremer & Pople (1975). For anthracene derivatives see: Alston et al. (1979); Kaplan & Conroy (1963); Meek et al. (1960); Singh & Ningombom (2010); Verma & Singh (1977). For hydrogen bonding, see: Bernstein et al. (1995).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KJ2220 ).
This project was supported by Research Center, Deanship of Scientific Research, College of Science, King Saud University.
Alston, P. V., Ottenbrite, R. M. & Newby, J. (1979). J. Org. Chem. 44, 4939-4943.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Kaplan, F. & Conroy, H. (1963). J. Org. Chem. 28, 1593-1596.
Meek, J. S., Wilgus, D. R. & Dann, J. R. (1960). J. Am. Chem. Soc. 82, 2566-2569.
Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Singh, M. D. & Ningombom, A. (2010). Indian J. Chem. Sect. B, 49, 789-794.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Verma, S. M. & Singh, M. D. (1977). J. Org. Chem. 42, 3736-3740.