Received 9 December 2012
aInstitute of Inorganic Chemistry, University of Hamburg, Hamburg, Germany,bDepartment of Chemical Engineering, United Arab Emirates University, Al Ain, Abu Dhabi, United Arab Emirates, and cDepartment of Chemistry, United Arab Emirates University, AL Ain, Abu Dhabi, United Arab Emirates
Correspondence e-mail: firstname.lastname@example.org
In the asymmetric unit of the title compound, C19H16O2, there are two symmetry-independent molecules (A and B) that differ in the conformation of the ester ethoxy group. In the crystal, the molecules form inversion dimers via pairs of C-HO interactions. Within the dimers, the anthracenyl units have interplanar distances of 0.528 (2) and 0.479 (2) Å for dimers of molecules A and B, respectively. Another short C-HO contact between symmetry-independent dimers links them into columns parallel to [10-1]. These columns are arranged into (111) layers and there are - stacking interactions [centroid-centroid distances = 3.6446 (15) and 3.6531 (15) Å] between the anthracenyl units from the neighbouring columns. In addition, there are C-H interactions between the anthracenyl unit of dimers A and dimers B within the same column.
For an analogous preparation of the title compound, see: Nguyen & Weizman (2007). For modeling of the title compound at the B3LYP/6-31G* level, see: Coleman (2007). For crystal structures of photodimerizable arylenes, see: Vishnumurthy et al. (2002); Mascitti & Corey (2006); Sonoda (2011); Schmidt (1964). For the photodimerization of anthracenes in the crystal, see: Schmidt (1971); Ihmels et al. (2000).
Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) within OLEX2 (Dolomanov et al., 2009); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 and PLATON.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2545 ).
The authors thank the UAEU interdisciplinary grant 31S036 for financial support. They also thank Thirumurugan Prakasam, NYU Abu Dhabi, for the mass spectrometry measurements.
Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Coleman, W. F. (2007). J. Chem. Educ. 84, 121-121.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.
Ihmels, H., Leusser, D., Pfeiffer, M. & Stalke, D. (2000). Tetrahedron, 56, 6867-6875.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.
Mascitti, V. & Corey, E. J. (2006). Tetrahedron Lett. 47, 5879-5882.
Nguyen, K. & Weizman, H. (2007). J. Chem. Educ. 84, 119-121.
Schmidt, G. M. J. (1964). J. Chem. Soc., pp. 2014-2021.
Schmidt, G. M. J. (1971). Pure Appl. Chem., 27, 647-678.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sonoda, Y. (2011). Molecules, 16, 119-148.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Vishnumurthy, K., Guru Row, T. N. & Venkatesan, K. (2002). Photochem. Photobiol. Sci. 1, 427-430.