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Volume 69 
Part 5 
Pages o687-o688  
May 2013  

Received 28 February 2013
Accepted 2 April 2013
Online 10 April 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.040
wR = 0.118
Data-to-parameter ratio = 15.6
Details
Open access

4-(4-Fluorophenyl)-6-methylamino-5-nitro-2-phenyl-4H-pyran-3-carbonitrile

aDepartment of Physics, The Madura College, Madurai 625 011, India,bDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India, and cDepartment of Food Science and Technology, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri Lanka
Correspondence e-mail: plakshmannilantha@ymail.com

In the title compound, C19H14FN3O3, the central pyran ring adopts a boat conformation with the O atom and the quaternary C atom diagonally opposite displaced by 0.068 (1) and 0.075 (1) Å, respectively, above the mean plane defined by the other four ring atoms. The co-planar atoms of the pyran ring and the fluorophenyl ring are nearly perpendicular, as evidenced by the dihedral angle of 87.11 (1)°. The amine group forms an intramolecular N-H...O(nitro) hydrogen bond. In the crystal, molecules are linked into parallel chains along [100] by weak N-H...N and C-H...N(nitro) hydrogen bonds, generating C(8) and C(9) graph-set motifs, respectively.

Related literature

For the biological activity of substituted pyran derivatives, see: Lokaj et al. (1990[Lokaj, J., Kettmann, V., Pavelcík, F., Ilavský, D. & Marchalín, S. (1990). Acta Cryst. C46, 788-791.]); Marco et al. (1993[Marco, J. L., Martín, G., Martín, N., Martínez-Grau, A., Seoane, C., Albert, A. & Cano, F. H. (1993). Tetrahedron, 49, 7133-7144.]). Some 4H-pyran derivatives are potential bioactive compounds and can be used as calcium antagonists, see: Suárez et al. (2002[Suárez, M., Salfrán, E., Verdecia, Y., Ochoa, E., Alba, L., Martín, N., Martínez, R., Quinteiro, M., Seoane, C., Novoa, H., Blaton, N., Peeters, O. M. & De Ranter, C. (2002). Tetrahedron, 58, 953-960.]). For hydrogen-bonding graph-set motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For ring conformation analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). The title compound and some related compounds are widely used as organic intermediates in organic chemistry (Liang et al., 2009[Liang, F., Cheng, X., Liu, J. & Liu, Q. (2009). Chem. Commun. pp. 3636-3638.]). For related structures, see: Nesterov et al. (2004[Nesterov, V. N., Wiedenfeld, D. J., Nesterova, S. V. & Minton, M. A. (2004). Acta Cryst. C60, o334-o337.]); Nesterov & Viltchinskaia (2001[Nesterov, V. N. & Viltchinskaia, E. A. (2001). Acta Cryst. C57, 616-618.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C19H14FN3O3

  • Mr = 351.33

  • Triclinic, [P \overline 1]

  • a = 9.3898 (3) Å

  • b = 9.9752 (3) Å

  • c = 11.1324 (3) Å

  • [alpha] = 98.765 (1)°

  • [beta] = 113.991 (1)°

  • [gamma] = 109.520 (1)°

  • V = 846.09 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 293 K

  • 0.23 × 0.20 × 0.19 mm

Data collection
  • Bruker Kappa APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.]) Tmin = 0.967, Tmax = 0.974

  • 16948 measured reflections

  • 3680 independent reflections

  • 2993 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.118

  • S = 1.06

  • 3680 reflections

  • 236 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2...O2 0.86 1.99 2.6089 (16) 128
N2-H2...N3i 0.86 2.30 2.9811 (17) 136
C6-H6A...N3i 0.96 2.60 3.222 (2) 123
Symmetry code: (i) x-1, y, z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2475 ).


Acknowledgements

JS thanks the UGC for the FIST support. JS and RV thank the management of the Madura College for their encouragement and support. RRK thanks the DST, New Delhi, for funds under the fast-track scheme (No. SR/FT/CS-073/2009).

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Liang, F., Cheng, X., Liu, J. & Liu, Q. (2009). Chem. Commun. pp. 3636-3638.  [CSD] [CrossRef]
Lokaj, J., Kettmann, V., Pavelcík, F., Ilavský, D. & Marchalín, S. (1990). Acta Cryst. C46, 788-791.  [CrossRef] [details]
Marco, J. L., Martín, G., Martín, N., Martínez-Grau, A., Seoane, C., Albert, A. & Cano, F. H. (1993). Tetrahedron, 49, 7133-7144.  [CrossRef] [ChemPort] [ISI]
Nesterov, V. N. & Viltchinskaia, E. A. (2001). Acta Cryst. C57, 616-618.  [CSD] [CrossRef] [ChemPort] [details]
Nesterov, V. N., Wiedenfeld, D. J., Nesterova, S. V. & Minton, M. A. (2004). Acta Cryst. C60, o334-o337.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Suárez, M., Salfrán, E., Verdecia, Y., Ochoa, E., Alba, L., Martín, N., Martínez, R., Quinteiro, M., Seoane, C., Novoa, H., Blaton, N., Peeters, O. M. & De Ranter, C. (2002). Tetrahedron, 58, 953-960.


Acta Cryst (2013). E69, o687-o688   [ doi:10.1107/S1600536813009008 ]

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