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Volume 69 
Part 5 
Page o647  
May 2013  

Received 8 March 2013
Accepted 23 March 2013
Online 5 April 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
R = 0.045
wR = 0.114
Data-to-parameter ratio = 13.7
Details
Open access

10-(3,5-Dinitrophenyl)-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 Laboratory of Fine Petrochemical Technology, Changzhou University, Changzhou 213164, People's Republic of China
Correspondence e-mail: hemingyangjpu@yahoo.com

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-H...F hydrogen bonds connect neighbouring molecules into inversion dimers, which are linked by further strong C-H...F interactions, forming a supramolecular layered array parallel to the bc plane.

Related literature

For the use of related compounds for fluorescence analysis, see: Weiner et al. (2001[Weiner, A. L., Lewis, A., Ottolenghi, M. & Sheves, M. (2001). J. Am. Chem. Soc. 123, 6612-6616.]); Gabe et al. (2004[Gabe, Y., Urano, Y., Kikuchi, K., Kojima, H. & Nagano, T. (2004). J. Am. Chem. Soc. 126, 3357-3367.]). For the structural characterization of related compounds, see: Euler et al. (2002a[Euler, H., Kirfel, A., Freudenthal, S. J. & Müller, C. E. (2002a). Z. Kristallogr. New Cryst. Struct. 217, 541-542.],b[Euler, H., Kirfel, A., Freudenthal, S. J. & Müller, C. E. (2002b). Z. Kristallogr. New Cryst. Struct. 217, 543-544.]); Cui et al. (2006[Cui, A.-J., Peng, X.-J., Gao, Y.-L. & Fan, J.-L. (2006). Acta Cryst. E62, o4697-o4698.]). For the synthetic procedure, see: Kollmannsberger et al. (1998[Kollmannsberger, M., Rurack, K., Resch-Genger, U. & Daub, J. (1998). J. Phys. Chem. A, 102, 10211-10220.]).

[Scheme 1]

Experimental

Crystal data
  • C19H17BF2N4O4

  • Mr = 414.18

  • Monoclinic, C 2/c

  • a = 29.016 (3) Å

  • b = 9.1763 (9) Å

  • c = 16.8294 (16) Å

  • [beta] = 121.086 (2)°

  • V = 3837.4 (7) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 295 K

  • 0.21 × 0.21 × 0.16 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.]) Tmin = 0.973, Tmax = 0.985

  • 11322 measured reflections

  • 3767 independent reflections

  • 2276 reflections with I > 2[sigma](I)

  • Rint = 0.035

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.114

  • S = 1.04

  • 3767 reflections

  • 275 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C5-H5...F2i 0.93 2.51 3.307 (2) 144
C13-H13A...F1ii 0.96 2.45 3.287 (2) 146
Symmetry codes: (i) [-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]; (ii) [x, -y+1, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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 ).


Acknowledgements

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.

References

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cui, A.-J., Peng, X.-J., Gao, Y.-L. & Fan, J.-L. (2006). Acta Cryst. E62, o4697-o4698.  [CSD] [CrossRef] [ChemPort] [details]
Euler, H., Kirfel, A., Freudenthal, S. J. & Müller, C. E. (2002a). Z. Kristallogr. New Cryst. Struct. 217, 541-542.  [ChemPort]
Euler, H., Kirfel, A., Freudenthal, S. J. & Müller, C. E. (2002b). Z. Kristallogr. New Cryst. Struct. 217, 543-544.  [ChemPort]
Gabe, Y., Urano, Y., Kikuchi, K., Kojima, H. & Nagano, T. (2004). J. Am. Chem. Soc. 126, 3357-3367.  [ISI] [CrossRef] [PubMed] [ChemPort]
Kollmannsberger, M., Rurack, K., Resch-Genger, U. & Daub, J. (1998). J. Phys. Chem. A, 102, 10211-10220.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Weiner, A. L., Lewis, A., Ottolenghi, M. & Sheves, M. (2001). J. Am. Chem. Soc. 123, 6612-6616.  [ISI] [PubMed]


Acta Cryst (2013). E69, o647  [ doi:10.1107/S1600536813008027 ]

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