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

Srinivasan, T.; Yuvaraj, P.; Reddy, B.S.R.; Velmurugan, D.

doi:10.1107/S1600536813001050

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 (C-C) = 0.002 Å
R = 0.040
wR = 0.118
Data-to-parameter ratio = 14.7
Details

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

Thothadri Srinivasan,^a Panneerselvam Yuvaraj,^b Boreddy S. R. Reddy ^b and Devadasan Velmurugan ^a ^*

^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-HO hydrogen bonds, leading to chains running along [011].

Related literature

For the uses and biological importance of diketones, see: Bennett et al. (1999); Sato et al. (2008). For a related structure, see: Öztürk Yildirim et al. (2012).

Experimental

Crystal data

C₁₈H₁₅NO₃
M_r = 293.31
Triclinic, $[P \overline 1]$
a = 7.4426 (6) Å
b = 10.5117 (9) Å
c = 10.6887 (9) Å
= 60.939 (4)°
= 88.107 (5)°
= 77.546 (5)°
V = 711.22 (10) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.972, T_max = 0.982
10655 measured reflections
2949 independent reflections
2427 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.118
S = 1.05
2949 reflections
201 parameters
H-atom parameters constrained
_max = 0.17 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C15-H15O2ⁱ	0.93	2.43	3.250 (2)	147
Symmetry code: (i) x-1, y+1, z-1.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

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.
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Öztürk Yildirim, S., Butcher, R. J., El-Khouly, A., Safak, C. & Simsek, R. (2012). Acta Cryst. E68, o3365-o3366.
Sato, K., Yamazoe, S., Yamamoto, R., Ohata, S., Tarui, A., Omote, M., Kumadaki, I. & Ando, A. (2008). Org. Lett. 10, 2405-2408.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Acknowledgements

References