[Journal logo]

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 [sigma](C-C) = 0.003 Å
R = 0.055
wR = 0.177
Data-to-parameter ratio = 21.3
Details
Open access

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

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-H...O 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[Aazam, E. S., Fawazy, A. & Hitchcock, P. B. (2006). Acta Cryst. E62, o4285-o4287.]); Chinnakali et al. (2009[Chinnakali, K., Sudha, D., Jayagobi, M., Raghunathan, R. & Fun, H.-K. (2009). Acta Cryst. E65, o2099-o2100.]); Du et al. (2010[Du, B.-X., Zhou, J., Li, Y.-L. & Wang, X.-S. (2010). Acta Cryst. E66, o1622.]); Pereira Silva et al. (2010[Pereira Silva, P. S., Parveen, M., Khanam, Z., Ali, A. & Ramos Silva, M. (2010). Acta Cryst. E66, o988.]). For ring conformational analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C22H21NO3

  • Mr = 347.40

  • Triclinic, [P \overline 1]

  • a = 7.7529 (4) Å

  • b = 11.2790 (7) Å

  • c = 11.7563 (11) Å

  • [alpha] = 117.232 (3)°

  • [beta] = 98.475 (3)°

  • [gamma] = 101.301 (2)°

  • V = 862.60 (11) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (1999). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.984, Tmax = 0.987

  • 18945 measured reflections

  • 5009 independent reflections

  • 3544 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.177

  • S = 1.03

  • 5009 reflections

  • 235 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.41 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C12-H12A...O1i 0.97 2.59 3.307 (3) 131
C20-H20...O2ii 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[Bruker (2004). APEX2 SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2 SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2 SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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: 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: 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.  [CSD] [CrossRef] [details]
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.  [CSD] [CrossRef] [ChemPort] [details]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Du, B.-X., Zhou, J., Li, Y.-L. & Wang, X.-S. (2010). Acta Cryst. E66, o1622.  [CSD] [CrossRef] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Pereira Silva, P. S., Parveen, M., Khanam, Z., Ali, A. & Ramos Silva, M. (2010). Acta Cryst. E66, o988.  [CrossRef] [details]
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, o280  [ doi:10.1107/S1600536813001876 ]

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.