Received 22 May 2013
The title compound, C26H24BF2N3O, comprises a boron-dipyrromethene (BODIPY) framework and a phenolic Schiff base substituent group. The BODIPY unit is close to planar [maximum deviation from the least-squares plane = 0.040 (3) Å], and forms a dihedral angle of 80.38 (13)° with the meso-substituent phenyl ring and an angle of 56.57 (13)° with the phenolic ring in the extended substituent chain. An intramolecular O-HN hydrogen bond is formed between the phenolic hydroxyl group and the Schiff base N-atom. The crystal studied was a non-merohedral twin with a BASF factor of 0.447 (3) for the two components.
For the photophysical properties of BODIPY dyes, see: Loudet & Burgess (2007); Boens et al. (2012). For the use of related compounds for fluorescence analysis, see: Fan et al. (2012); Li et al. (2012). For the preparation of the BODIPY precursor, see: Lu et al. (2009).
Data collection: CrystalClear-SM Expert (Rigaku, 2009); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert (Rigaku, 2009); 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: CrystalStructure.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2263 ).
We gratefully acknowledge the Analysis Center of Nankai University.
Boens, N., Leen, V. & Dehaen, W. (2012). Chem. Soc. Rev. 41, 1130-1172.
Fan, J., Liu, X., Hu, M., Zhu, H., Song, F. & Peng, X. (2012). Anal. Chim. Acta, 735, 107-113.
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Li, Q., Guo, Y. & Shao, S. (2012). Sens. Actuators B, 171, 872-877.
Loudet, A. & Burgess, K. (2007). Chem. Rev. 107, 4891-4932.
Lu, H., Zhang, S., Liu, H., Wang, Y., Shen, Z., Liu, C. & You, X. (2009). J. Phys. Chem. A 113, 14081-14086.
Rigaku (2009). CrystalClear-SM Expert and CrystalStructure. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.