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Volume 69 
Part 3 
Page o451  
March 2013  

Received 13 February 2013
Accepted 20 February 2013
Online 28 February 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.040
wR = 0.116
Data-to-parameter ratio = 16.3
Details
Open access

4-(4-Methoxyphenyl)-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, C20H17N3O4, the central pyran ring adopts a boat conformation with the O atom and diagonally opposite C atoms displaced by 0.1171 (1) and 0.1791 (1) Å, respectively, from the mean plane defined by the other four atoms. The coplanar atoms of the pyran ring and the methoxybenzene ring are nearly perpendicular, as evidenced by the dihedral angle 87.01 (1)°. The amine H atom forms an intramolecular N-H...O(nitro) hydrogen bond. In the crystal, molecules are linked into dimeric aggregates by N-H...O(nitro) hydrogen bonds, generating an R22(12) graph-set motif.

Related literature

For background to compounds containing the 4H-pyran unit, see: Brahmachari (2010[Brahmachari, G. (2010). In Handbook of Pharmaceutical Natural Products. Weinheim: Wiley-VCH Verlag GmbH & Co.]); Hatakeyama et al. (1988[Hatakeyama, S., Ochi, N., Numata, H. & Takano, S. (1988). J. Chem. Soc. Chem. Commun. pp. 1202-1204.]). For 2-amino-4H-pyrans as photoactive materials, see: Armetso et al. (1989[Armetso, D., Horspool, W. M., Martin, N., Ramos, A. & Seoane, C. (1989). J. Org. Chem. 54, 3069-3072.]). For 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.]).

[Scheme 1]

Experimental

Crystal data
  • C20H17N3O4

  • Mr = 363.37

  • Monoclinic, C 2/c

  • a = 22.9422 (10) Å

  • b = 7.5828 (3) Å

  • c = 22.7319 (10) Å

  • [beta] = 112.576 (2)°

  • V = 3651.5 (3) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.23 × 0.21 × 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

  • 15550 measured reflections

  • 4003 independent reflections

  • 2915 reflections with I > 2[sigma](I)

  • Rint = 0.028

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

  • wR(F2) = 0.116

  • S = 1.05

  • 4003 reflections

  • 246 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.18 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 2.00 2.6203 (19) 128
N2-H2...O2i 0.86 2.26 3.0114 (18) 147
Symmetry code: (i) -x, -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: TK5197 ).


Acknowledgements

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

References

Armetso, D., Horspool, W. M., Martin, N., Ramos, A. & Seoane, C. (1989). J. Org. Chem. 54, 3069-3072.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Brahmachari, G. (2010). In Handbook of Pharmaceutical Natural Products. Weinheim: Wiley-VCH Verlag GmbH & Co.
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]
Hatakeyama, S., Ochi, N., Numata, H. & Takano, S. (1988). J. Chem. Soc. Chem. Commun. pp. 1202-1204.  [CrossRef] [ISI]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o451  [ doi:10.1107/S1600536813004923 ]

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