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

Wang, X.

doi:10.1107/S1600536811008130

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 (C-C) = 0.004 Å
R = 0.045
wR = 0.114
Data-to-parameter ratio = 13.9
Details

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

Xiaoli Wang ^a ^*

^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-HN and N-HO 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); Marco et al. (1993). For the crystal structure of a related compound, see: Tu et al. (2001).

Experimental

Crystal data

C₁₆H₁₄N₂O₂
M_r = 266.29
Monoclinic, C 2/c
a = 20.210 (2) Å
b = 8.8161 (5) Å
c = 16.3862 (13) Å
= 99.537 (1)°
V = 2879.2 (4) Å³
Z = 8
Mo K radiation
= 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) T_min = 0.974, T_max = 0.988
7077 measured reflections
2535 independent reflections
1083 reflections with I > 2(I)
R_int = 0.063

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.114
S = 0.81
2535 reflections
182 parameters
H-atom parameters constrained
_max = 0.12 e Å^-3
_min = -0.11 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AN2ⁱ	0.86	2.16	3.007 (3)	170
N1-H1BO2ⁱⁱ	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); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); 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.
Marco, J. L., Martin, G., Martin, N., Martinez-Grau, A., Seoane, C., Albert, A. & Cano, F. H. (1993). Tetrahedron, 49, 7133-7144.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tu, S.-J., Deng, X., Fang, Y.-Y., Guo, Y.-M., Du, M. & Liu, X.-H. (2001). Acta Cryst. E57, o358-o359.

organic compounds