Received 8 January 2013
The asymmetric unit of the title compound, C25H31NO4, contains two independent molecules. In one molecule, the benzene ring and an attached methoxy group were refined as disordered over two sets of sites in a 0.65 (4): 0.35 (4) ratio. In both molecules, the central ring of the acridinedione system adopts a flattened boat conformation. The four essentially planar atoms of this ring [maximum deviations = 0.006 (5) Å in both molecules] forms dihedral angles of 86.8 (2) and 87.6 (2)°, respectively, with the major and minor components in the disordered benzene ring and 87.3 (2)° with the benzene ring in the fully ordered molecule. The two outer rings of the acridinedione system adopt sofa conformations in both molecules. In the crystal, N-HO hydrogen bonds form two independent chains along . C-HO hydrogen bonds link the chains, forming a three-dimensional network.
For applications of acridines, see: Murugan et al. (1998); Leon et al. (2008); Josephrajan et al. (2005); Srividya et al. (1998, 1996). For related structures, see: Balamurugan et al. (2009); Zhao & Teng (2008); Kant et al. (2013a,b). For ring conformations, see: Duax & Norton (1975).
Data collection: CrysAlis PRO (Oxford Diffraction, 2010); 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); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: PLATON.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5574 ).
RK acknowledges the Department of Science & Technology for access to the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003.
Balamurugan, P., Jagan, R., Thiagarajan, V. M., Yamin, B. & Sivakumar, K. (2009). Acta Cryst. E65, o271.
Duax, W. L. & Norton, D. A. (1975). Atlas of Steroid Structures, Vol. 1. New York: Plenum Press.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Josephrajan, T., Ramakrishnan, V. T., Kathiravan, G. & Muthumary, J. (2005). ARKIVOC, pp. 124-136.
Kant, R., Gupta, V. K., Kapoor, K., Patil, D. R., Patil, P. P. & Deshmukh, M. B. (2013a). Acta Cryst. E69, o100.
Kant, R., Gupta, V. K., Kapoor, K., Patil, D. R., Jagadale, S. D. & Deshmukh, M. B. (2013b). Acta Cryst. E69, o101.
Leon, R., Rios, C., Contelles, J. M., Lopez, G. M., Garcia, A. G. & Villarroya, M. (2008). Eur. J. Med. Chem. 43, 668-674.
Murugan, P., Shanmugasundaram, P., Ramakrishnan, V. T., Venkatachalapathy, B., Srividya, N., Ramamurthy, P., Gunasekaran, K. & Velmurugan, D. (1998). J. Chem. Soc. Perkin Trans. 2, pp. 999-1003.
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Srividya, N., Ramamurthy, P. & Ramakrishnan, V. T. (1998). Spectrochim. Acta Part A, 54, 245-253.
Srividya, N., Ramamurthy, P., Shanmugasundaram, P. & Ramakrishnan, V. T. (1996). J. Org. Chem. 61, 5083-5089.
Zhao, L.-L. & Teng, D. (2008). Acta Cryst. E64, o1772-o1773.