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Volume 67 
Part 4 
Page o832  
April 2011  

Received 12 January 2011
Accepted 3 March 2011
Online 9 March 2011

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.004 Å
R = 0.045
wR = 0.114
Data-to-parameter ratio = 13.9
Details
Open access

2-Amino-5-oxo-4-phenyl-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile

aSchool of Petrochemical Engineering, Shenyang University of Technology, Liaoyang 111003, People's Republic of China
Correspondence e-mail: xlwangsut@163.com

In the title molecule, C16H14N2O2, the fused cyclohexene and pyran rings adopt an envelope and a flattened boat conformation, respectively. In the crystal, N-H...N and N-H...O hydrogen bonds link the molecules into corrugated sheets parallel to the bc plane.

Related literature

For the biological activities 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., Martin, G., Martin, N., Martinez-Grau, A., Seoane, C., Albert, A. & Cano, F. H. (1993). Tetrahedron, 49, 7133-7144.]). For the crystal structure of a related compound, see: Tu et al. (2001[Tu, S.-J., Deng, X., Fang, Y.-Y., Guo, Y.-M., Du, M. & Liu, X.-H. (2001). Acta Cryst. E57, o358-o359.]).

[Scheme 1]

Experimental

Crystal data
  • C16H14N2O2

  • Mr = 266.29

  • Monoclinic, C 2/c

  • a = 20.210 (2) Å

  • b = 8.8161 (5) Å

  • c = 16.3862 (13) Å

  • [beta] = 99.537 (1)°

  • V = 2879.2 (4) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 298 K

  • 0.32 × 0.21 × 0.15 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.974, Tmax = 0.988

  • 7077 measured reflections

  • 2535 independent reflections

  • 1083 reflections with I > 2[sigma](I)

  • Rint = 0.063

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

  • wR(F2) = 0.114

  • S = 0.81

  • 2535 reflections

  • 182 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.12 e Å-3

  • [Delta][rho]min = -0.11 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...N2i 0.86 2.16 3.007 (3) 170
N1-H1B...O2ii 0.86 2.00 2.848 (2) 169
Symmetry codes: (i) -x, -y+1, -z+2; (ii) [x, -y+2, z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART 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: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5040 ).


Acknowledgements

The author acknowledges financial support from the Shenyang University of Technology.

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Lokaj, J., Kettmann, V., Pavelcík, F., Ilavský, D. & Marchalín, S. (1990). Acta Cryst. C46, 788-791.  [CrossRef] [details]
Marco, J. L., Martin, G., Martin, N., Martinez-Grau, A., Seoane, C., Albert, A. & Cano, F. H. (1993). Tetrahedron, 49, 7133-7144.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tu, S.-J., Deng, X., Fang, Y.-Y., Guo, Y.-M., Du, M. & Liu, X.-H. (2001). Acta Cryst. E57, o358-o359.  [CSD] [CrossRef] [details]


Acta Cryst (2011). E67, o832  [ doi:10.1107/S1600536811008130 ]

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