rac-4a,10b-cis,10b,5c-trans-5-(7-Methyl-2-oxo-2H-chromen-4-yl)-3,4,4a,5,6,10b-hexa­hydro-2H-pyrano[3,2-c]quinoline

Kayalvizhi, M.; Vasuki, G.; Samant, S.D.; Sanap, K.K.

doi:10.1107/S1600536813001876

Volume 69
Part 2
Page o280
February 2013

Received 17 December 2012
Accepted 18 January 2013
Online 23 January 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.055
wR = 0.177
Data-to-parameter ratio = 21.3
Details

rac-4a,10b-cis,10b,5c-trans-5-(7-Methyl-2-oxo-2H-chromen-4-yl)-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline

M. Kayalvizhi,^a G. Vasuki,^a ^* Shriniwas D. Samant ^b and Kailas K. Sanap ^b

^aDepartment of Physics, Kunthavai Naachiar Government Arts College (W) (Autonomous), Thanjavur-7, India, and ^bDepartment of Chemistry, Institute of Chemical Technology, N.M. Parekh Road, Matunga, Mumbai 400 019, India
Correspondence e-mail: vasuki.arasi@yahoo.com

In the racemic title compound, C₂₂H₂₁NO₃, the nitrogen-containing ring of the pyranoquinoline moiety adopts a slightly distorted half-chair conformation and the oxygen-containing ring adopts a slightly distorted chair conformation. The benzene rings make a dihedral angle of 84.97 (8)°. In the crystal, weak C-HO interactions link the molecules into chains extending along the a-axis direction.

Related literature

For general background and related coumarin compounds, see: Aazam et al. (2006); Chinnakali et al. (2009); Du et al. (2010); Pereira Silva et al. (2010). For ring conformational analysis, see: Cremer & Pople (1975).

Experimental

Crystal data

C₂₂H₂₁NO₃
M_r = 347.40
Triclinic, $[P \overline 1]$
a = 7.7529 (4) Å
b = 11.2790 (7) Å
c = 11.7563 (11) Å
= 117.232 (3)°
= 98.475 (3)°
= 101.301 (2)°
V = 862.60 (11) Å³
Z = 2
Mo K radiation
= 0.09 mm^-1
T = 296 K
0.20 × 0.15 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker 1999) T_min = 0.984, T_max = 0.987
18945 measured reflections
5009 independent reflections
3544 reflections with I > 2(I)
R_int = 0.030

Refinement

R[F² > 2(F²)] = 0.055
wR(F²) = 0.177
S = 1.03
5009 reflections
235 parameters
H-atom parameters constrained
_max = 0.41 e Å^-3
_min = -0.27 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C12-H12AO1ⁱ	0.97	2.59	3.307 (3)	131
C20-H20O2ⁱⁱ	0.93	2.40	3.275 (2)	157
Symmetry codes: (i) -x+2, -y+2, -z; (ii) x+1, y, z.

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); 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: PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2247 ).

Acknowledgements

The authors thank the Sophisticated Analytical Instrument Facility, IIT-Madras, Chennai, for the data collection.

References

Aazam, E. S., Fawazy, A. & Hitchcock, P. B. (2006). Acta Cryst. E62, o4285-o4287.
Bruker (1999). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2004). APEX2 SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Chinnakali, K., Sudha, D., Jayagobi, M., Raghunathan, R. & Fun, H.-K. (2009). Acta Cryst. E65, o2099-o2100.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Du, B.-X., Zhou, J., Li, Y.-L. & Wang, X.-S. (2010). Acta Cryst. E66, o1622.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Pereira Silva, P. S., Parveen, M., Khanam, Z., Ali, A. & Ramos Silva, M. (2010). Acta Cryst. E66, o988.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.