[Journal logo]

Volume 69 
Part 2 
Page o254  
February 2013  

Received 4 January 2013
Accepted 11 January 2013
Online 19 January 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.040
wR = 0.118
Data-to-parameter ratio = 14.7
Details
Open access

8,8-Dimethyl-8,9-dihydro-7H-chromeno[2,3-b]quinoline-10,12-dione

aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and bIndustrial Chemistry Laboratory, Central Leather Research Institute, Adyar, Chennai 600 020, India
Correspondence e-mail: shirai2011@gmail.com

In the title compound, C18H15NO3, the fused benzopyran and pyridine rings are essentially coplanar [r.m.s. deviation = 0.0533 Å with a maximum deviation of 0.080 (1) Å for a benzene C atom]. The cyclohexanone ring adopts an envelope conformation with the dimethyl-substituted C atom 0.660 (2) Å out of the plane formed by the remaining ring atoms (r.m.s. deviation = 0.0305 Å). The dihedral angle between the mean planes of the pyran and cyclohexanone rings is 12.95 (6)°. In the crystal, molecules are linked via C-H...O hydrogen bonds, leading to chains running along [011].

Related literature

For the uses and biological importance of diketones, see: Bennett et al. (1999[Bennett, I., Broom, N. J. P., Cassels, R., Elder, J. S., Masson, N. D. & O'Hanlon, P. J. (1999). Bioorg. Med. Chem. Lett. 9, 1847-1852.]); Sato et al. (2008[Sato, K., Yamazoe, S., Yamamoto, R., Ohata, S., Tarui, A., Omote, M., Kumadaki, I. & Ando, A. (2008). Org. Lett. 10, 2405-2408.]). For a related structure, see: Öztürk Yildirim et al. (2012)[Öztürk Yildirim, S., Butcher, R. J., El-Khouly, A., Safak, C. & Simsek, R. (2012). Acta Cryst. E68, o3365-o3366.].

[Scheme 1]

Experimental

Crystal data
  • C18H15NO3

  • Mr = 293.31

  • Triclinic, [P \overline 1]

  • a = 7.4426 (6) Å

  • b = 10.5117 (9) Å

  • c = 10.6887 (9) Å

  • [alpha] = 60.939 (4)°

  • [beta] = 88.107 (5)°

  • [gamma] = 77.546 (5)°

  • V = 711.22 (10) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.972, Tmax = 0.982

  • 10655 measured reflections

  • 2949 independent reflections

  • 2427 reflections with I > 2[sigma](I)

  • Rint = 0.031

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

  • wR(F2) = 0.118

  • S = 1.05

  • 2949 reflections

  • 201 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C15-H15...O2i 0.93 2.43 3.250 (2) 147
Symmetry code: (i) x-1, y+1, z-1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. 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: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2617 ).


Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. TS also thanks the DST for an Inspire fellowship.

References

Bennett, I., Broom, N. J. P., Cassels, R., Elder, J. S., Masson, N. D. & O'Hanlon, P. J. (1999). Bioorg. Med. Chem. Lett. 9, 1847-1852.  [CrossRef] [PubMed] [ChemPort]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Öztürk Yildirim, S., Butcher, R. J., El-Khouly, A., Safak, C. & Simsek, R. (2012). Acta Cryst. E68, o3365-o3366.  [CSD] [CrossRef] [details]
Sato, K., Yamazoe, S., Yamamoto, R., Ohata, S., Tarui, A., Omote, M., Kumadaki, I. & Ando, A. (2008). Org. Lett. 10, 2405-2408.  [ISI] [CrossRef] [PubMed] [ChemPort]
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, o254  [ doi:10.1107/S1600536813001050 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.