Received 8 March 2013
In an effort to discover new potential boron-dipyrromethene (BODIPY) dyes, the title compound, C19H17BF2N4O4, was prepared from 2,4-dimethylpyrrole, 3,5-dinitrobenzaldehyde and boron trifluoride in a one-pot reaction. The BODIPY fragment is nearly planar, with a maximum deviation from the least-squares plane of 0.251 (2) Å, and the benzene ring is inclined at a dihedral angle of 86.8 (6)° to the BODIPY mean plane. In the crystal, pairs of C-HF hydrogen bonds connect neighbouring molecules into inversion dimers, which are linked by further strong C-HF interactions, forming a supramolecular layered array parallel to the bc plane.
For the use of related compounds for fluorescence analysis, see: Weiner et al. (2001); Gabe et al. (2004). For the structural characterization of related compounds, see: Euler et al. (2002a,b); Cui et al. (2006). For the synthetic procedure, see: Kollmannsberger et al. (1998).
Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 and SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2539 ).
We gratefully acknowledge the financial support from the Open Foundation of Jiangsu Province Key Laboratory of Fine Petrochemical Technology (KF1005) and the Analysis Center of Changzhou University.
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