[Journal logo]

Volume 69 
Part 7 
Page o1072  
July 2013  

Received 22 May 2013
Accepted 4 June 2013
Online 12 June 2013

Key indicators
Single-crystal X-ray study
T = 113 K
Mean [sigma](C-C) = 0.005 Å
R = 0.071
wR = 0.217
Data-to-parameter ratio = 17.0
Details
Open access

10-{4-[(2-Hydroxybenzylidene)amino]phenyl}-5,5-difluoro-1,3,7,9-tetramethyl-5H-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-5-uide

aKey Laboraory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Zhongguancun Donglu 29, 100190 Beijing, People's Republic of China
Correspondence e-mail: lizhensheng0723@hotmail.com

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-H...N 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.

Related literature

For the photophysical properties of BODIPY dyes, see: Loudet & Burgess (2007[Loudet, A. & Burgess, K. (2007). Chem. Rev. 107, 4891-4932.]); Boens et al. (2012[Boens, N., Leen, V. & Dehaen, W. (2012). Chem. Soc. Rev. 41, 1130-1172.]). For the use of related compounds for fluorescence analysis, see: Fan et al. (2012[Fan, J., Liu, X., Hu, M., Zhu, H., Song, F. & Peng, X. (2012). Anal. Chim. Acta, 735, 107-113.]); Li et al. (2012[Li, Q., Guo, Y. & Shao, S. (2012). Sens. Actuators B, 171, 872-877.]). For the preparation of the BODIPY precursor, see: Lu et al. (2009[Lu, H., Zhang, S., Liu, H., Wang, Y., Shen, Z., Liu, C. & You, X. (2009). J. Phys. Chem. A 113, 14081-14086.]).

[Scheme 1]

Experimental

Crystal data
  • C26H24BF2N3O

  • Mr = 443.29

  • Triclinic, [P \overline 1]

  • a = 8.8920 (15) Å

  • b = 10.7480 (17) Å

  • c = 12.9230 (18) Å

  • [alpha] = 110.258 (9)°

  • [beta] = 90.952 (6)°

  • [gamma] = 108.408 (7)°

  • V = 1088.3 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 113 K

  • 0.24 × 0.20 × 0.18 mm

Data collection
  • Rigaku Saturn724 CCD-detector diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.978, Tmax = 0.983

  • 12167 measured reflections

  • 5171 independent reflections

  • 2822 reflections with I > 2[sigma](I)

  • Rint = 0.054

Refinement
  • R[F2 > 2[sigma](F2)] = 0.071

  • wR(F2) = 0.217

  • S = 1.09

  • 5171 reflections

  • 304 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.77 e Å-3

  • [Delta][rho]min = -0.44 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N3 0.84 1.89 2.618 (4) 145

Data collection: CrystalClear-SM Expert (Rigaku, 2009[Rigaku (2009). CrystalClear-SM Expert and CrystalStructure. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert (Rigaku, 2009[Rigaku (2009). CrystalClear-SM Expert and CrystalStructure. Rigaku Corporation, Tokyo, Japan.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: CrystalStructure.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2263 ).


Acknowledgements

We gratefully acknowledge the Analysis Center of Nankai University.

References

Boens, N., Leen, V. & Dehaen, W. (2012). Chem. Soc. Rev. 41, 1130-1172.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Fan, J., Liu, X., Hu, M., Zhu, H., Song, F. & Peng, X. (2012). Anal. Chim. Acta, 735, 107-113.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Li, Q., Guo, Y. & Shao, S. (2012). Sens. Actuators B, 171, 872-877.  [CrossRef]
Loudet, A. & Burgess, K. (2007). Chem. Rev. 107, 4891-4932.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Lu, H., Zhang, S., Liu, H., Wang, Y., Shen, Z., Liu, C. & You, X. (2009). J. Phys. Chem. A 113, 14081-14086.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Rigaku (2009). CrystalClear-SM Expert and CrystalStructure. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1072  [ doi:10.1107/S1600536813015523 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.