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Volume 69 
Part 2 
Page o253  
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) = 0.003 Å
R = 0.053
wR = 0.167
Data-to-parameter ratio = 17.9
Details
Open access

2-Chloro-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

The asymmetric unit of the title compound, C18H14ClNO3, contains two independent molecules (A and B). In both molecules, the cyclohexanone ring has a chair conformation. The dihedral angles between the pyran ring and the pyridine and chlorophenyl rings are 2.13 (9) and 2.19 (9)°, respectively, in A, and 0.82 (9) and 1.93 (9)°, respectively, in B. The carbonyl O atoms deviate from the pyran and benzene rings to which they are attached by -0.092 (2) and 0.064 (2) Å, respectively, in A, and by -0.080 (2) and -0.063 (2) Å, respectively, in B. In the crystal, the A molecules are linked via C-H...O hydrogen bonds, forming double-stranded chains along [100]. They lie parallel to the double-stranded chains formed by the B molecules, which are also linked via C-H...O hydrogen bonds. The chains stack up the c axis in an -A-A-B-B-A-A- manner, with a number of [pi]-[pi] interactions involving A and B molecules; the centroid-centroid distances vary from 3.4862 (11) to 3.6848 (11) Å

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
  • C18H14ClNO3

  • Mr = 327.75

  • Triclinic, [P \overline 1]

  • a = 11.4135 (4) Å

  • b = 11.6663 (5) Å

  • c = 13.5810 (6) Å

  • [alpha] = 69.265 (3)°

  • [beta] = 73.868 (2)°

  • [gamma] = 64.998 (5)°

  • V = 1515.11 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.27 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 = 0.924, Tmax = 0.949

  • 26747 measured reflections

  • 7488 independent reflections

  • 5384 reflections with I > 2[sigma](I)

  • Rint = 0.033

Refinement
  • R[F2 > 2[sigma](F2)] = 0.053

  • wR(F2) = 0.167

  • S = 0.99

  • 7488 reflections

  • 419 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.33 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2...O3i 0.93 2.33 3.255 (3) 174
C2'-H2'...O3'i 0.93 2.38 3.309 (3) 173
Symmetry code: (i) x+1, y-1, z.

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 for Windows (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: SU2550 ).


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, o253  [ doi:10.1107/S1600536813001062 ]

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