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Volume 68 
Part 1 
Page o63  
January 2012  

Received 2 November 2011
Accepted 3 December 2011
Online 10 December 2011

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.006 Å
R = 0.083
wR = 0.193
Data-to-parameter ratio = 12.8
Details
Open access

{2-[(3,5-Dimethyl-2H-pyrrol-2-ylidene-[kappa]N)(4-nitrophenyl)methyl]-3,5-dimethyl-1H-pyrrol-1-ido-[kappa]N}difluoridoboron

aKey Laboratory of Fine Petrochemical Technology, Changzhou University, Changzhou 213164, People's Republic of China
Correspondence e-mail: aijuncui@yahoo.com

In an effort to discover novel and potential boron-dipyrromethene (BODIPY) dyes, the title compound, C19H18BF2N3O2, was prepared from 2,4-dimethylpyrrole, 4-nitrobenzaldehyde and BF3·Et2O in a one-pot reaction. There are two independent molecules, A and B, in the asymmetric unit in which the dihedral angles between the benzene ring and boron-dipyrromethene mean plane have significantly different values [82.71 (8)° for molecule A and 73.16 (8)° for molecule B]. Intermolecular C-H...[pi] interactions help to stabilize the crystal structure.

Related literature

For the use of related compounds in 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 related structures, 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
  • C19H18BF2N3O2

  • Mr = 369.17

  • Monoclinic, C 2/c

  • a = 30.5729 (6) Å

  • b = 11.8625 (2) Å

  • c = 19.8975 (5) Å

  • [beta] = 96.732 (1)°

  • V = 7166.5 (3) Å3

  • Z = 16

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 295 K

  • 0.60 × 0.31 × 0.12 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.]) Tmin = 0.961, Tmax = 0.989

  • 10802 measured reflections

  • 6278 independent reflections

  • 4790 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.083

  • wR(F2) = 0.193

  • S = 1.26

  • 6278 reflections

  • 492 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N4/C26/C28/C29/C31 and N5/C21-C23/C25 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C18-H18A...Cg1 0.93 2.93 3.784 (4) 154
C35-H35A...Cg2i 0.93 2.90 3.648 (5) 139
Symmetry code: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -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: IM2338 ).


Acknowledgements

We gratefully acknowledge 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] [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] [details]
Weiner, A. L., Lewis, A., Ottolenghi, M. & Sheves, M. (2001). J. Am. Chem. Soc. 123, 6612-6616.  [ISI] [PubMed]


Acta Cryst (2012). E68, o63  [ doi:10.1107/S1600536811052196 ]

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