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Volume 65 
Part 10 
Page o2561  
October 2009  

Received 14 September 2009
Accepted 22 September 2009
Online 26 September 2009

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.061
wR = 0.149
Data-to-parameter ratio = 9.7
Details
Open access

(RS)-3-Acetyl-2-methyl-4-(3-nitrophenyl)-1,4,5,6,7,8-hexahydroquinolin-5-one

aDepartment of Chemistry, Kashgar Teachers' College, Kashgar 844000, People's Republic of China
Correspondence e-mail: m_turhong@126.com,

In the title compound, C18H18N2O4, the nitro group, a methyl group, the acetyl group and some atoms of the dihydroquinolinone group are disordered over two sites with the ratio of occupancies fixed at 0.57:0.43. The relationship between the major and minor components of disorder is that of diastereomers. In the crystal structure, intermolecular N-H...O, weak C-H...O and C-H...[pi] interactions link the molecules into two-dimensional layers running parallel to the (010) plane.

Related literature

For the biological importance of polyhydroquinoline derivatives, see: Ko & Yao (2006[Ko, S. K. & Yao, C. F. (2006). Tetrahedron, 62, 7293-7299.]). For bond-length data, 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
  • C18H18N2O4

  • Mr = 326.34

  • Monoclinic, P 21 /n

  • a = 8.5368 (5) Å

  • b = 17.0307 (6) Å

  • c = 11.4759 (5) Å

  • [beta] = 106.143 (1)°

  • V = 1602.67 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 298 K

  • 0.20 × 0.10 × 0.10 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 = 0.971, Tmax = 0.990

  • 9050 measured reflections

  • 3151 independent reflections

  • 1611 reflections with I > 2[sigma](I)

  • Rint = 0.094

Refinement
  • R[F2 > 2[sigma](F2)] = 0.061

  • wR(F2) = 0.149

  • S = 0.90

  • 3151 reflections

  • 325 parameters

  • 12 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2A...O3i 0.868 (10) 2.063 (13) 2.927 (8) 173 (2)
C6-H6...O4i 0.93 2.56 3.309 (16) 138
C18-H18A...O1i 0.96 2.46 3.239 (18) 138
C18-H18B...O3i 0.96 2.57 3.422 (15) 148
C11-H11A...O1ii 0.97 2.55 3.290 (16) 133
C12-H12A...Cg1iii 0.97 2.76 3.71 (1) 166
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) x, y, z-1; (iii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]. Cg1 is the centroid of the C1-C6 ring.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2001[Bruker (2001). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; 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: PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2906 ).


Acknowledgements

The authors thank Kashgar Teachers? College for financial support.

References

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.
Bruker (2001). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Ko, S. K. & Yao, C. F. (2006). Tetrahedron, 62, 7293-7299.  [ISI] [CrossRef] [ChemPort]
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 (2009). E65, o2561  [ doi:10.1107/S160053680903832X ]

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