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Volume 69 
Part 6 
Page o986  
June 2013  

Received 16 March 2013
Accepted 20 May 2013
Online 31 May 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.049
wR = 0.126
Data-to-parameter ratio = 12.5
Details
Open access

[6-(Furan-2-yl)-7-nitro-2,3,4,6,7,8-hexahydro-1H-pyrido[1,2-a]pyrimidin-9-yl](phenyl)methanone

aCollege of Chemistry and Chemical Engineering, Jiang Xi Normal University, Nanchang, Jiang Xi 330022, People's Republic of China, and bBeijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, People's Republic of China
Correspondence e-mail: yucy@iccas.ac.cn

The asymmetric unit of the title compound, C19H19N3O4, contains two molecules with very few conformational differences; a C atom in the pyrimidine ring in one of the molecules is disordered in a 0.688 (15):0.312 (15) ratio. In both molecules, the fused pyridine and pyrimidine rings adopt half-chair conformations. The dihedral angles between the furan and benzene rings are 81.00 (13) and 84.99 (10)° in the two molecules. The molecular structure is consolidated by intramolecular N-H...O hydrogen bonding. In the crystal, C-H...O hydrogen bonds connect the molecules into a three-dimensional network.

Related literature

For background to heterocyclic ketene aminals, see: Yaqub et al. (2008[Yaqub, M., Yu, C.-Y., Jia, Y.-M. & Huang, Z.-T. (2008). Synlett, 9, 1357-1360.]); Huang & Wang (1994[Huang, Z.-T. & Wang, M.-X. (1994). Heterocycles, 37, 1233-1262.]); Yu et al. (2006[Yu, C.-Y., Yang, P.-H., Zhao, M.-X. & Huang, Z.-T. (2006). Synlett, pp. 1835-1840.]); For the crystal structure of a related compound, see: Yu et al. (2007[Yu, C.-Y., Yuan, X.-N. & Huang, Z.-T. (2007). Acta Cryst. E63, o3186.]).

[Scheme 1]

Experimental

Crystal data
  • C19H19N3O4

  • Mr = 353.37

  • Monoclinic, P 21 /c

  • a = 13.506 (3) Å

  • b = 17.675 (4) Å

  • c = 14.755 (3) Å

  • [beta] = 105.12 (3)°

  • V = 3400.3 (12) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 173 K

  • 0.44 × 0.43 × 0.37 mm

Data collection
  • Rigaku R-AXIS RAPID IP area-detector diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.958, Tmax = 0.964

  • 11765 measured reflections

  • 5990 independent reflections

  • 4405 reflections with I > 2[sigma](I)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.126

  • S = 1.02

  • 5990 reflections

  • 479 parameters

  • 40 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.59 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1A-H1AA...O1A 0.88 1.84 2.553 (2) 137
N1B-H1BA...O1B 0.88 1.85 2.556 (3) 136
C6A-H6AA...O1B 1.00 2.36 3.103 (3) 130
C7A-H7AB...O2A 0.99 2.44 2.790 (3) 100

Data collection: RAPID-AUTO (Rigaku, 2001[Rigaku (2001). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELX97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2626 ).


Acknowledgements

We thank Tongling Liang and Xiang Hao at the Chinese Academy of Sciences for the X-ray crystallographic determination.

References

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Huang, Z.-T. & Wang, M.-X. (1994). Heterocycles, 37, 1233-1262.  [CrossRef] [ChemPort]
Rigaku (2001). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Yaqub, M., Yu, C.-Y., Jia, Y.-M. & Huang, Z.-T. (2008). Synlett, 9, 1357-1360.
Yu, C.-Y., Yang, P.-H., Zhao, M.-X. & Huang, Z.-T. (2006). Synlett, pp. 1835-1840.  [ISI] [CrossRef]
Yu, C.-Y., Yuan, X.-N. & Huang, Z.-T. (2007). Acta Cryst. E63, o3186.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o986  [ doi:10.1107/S160053681301386X ]

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