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Volume 69 
Part 2 
Pages o267-o268  
February 2013  

Received 10 December 2012
Accepted 12 January 2013
Online 19 January 2013

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Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.045
wR = 0.133
Data-to-parameter ratio = 14.6
Details
Open access

(6bS*,14R*,14aR*)-Methyl 14-(4-methylphenyl)-7-oxo-6b,6c,7,12b,14,14a-hexahydro-1H-pyrano[3,2-c:5,4-c']dichromene-14a-carboxylate

R. Ponnusamy,a V. Sabari,b G. Sivakumar,c M. Bakthadossc and S. Aravindhanb*

aDepartment of Computer Science & Engineering, Madha Engineering College, Kundrathur, Chennai 600 069, India,bDepartment of Physics, Presidency College, Chennai 600 005, India, and cDepartment of Organic Chemistry, University of Madras, Chennai 600 025, India
Correspondence e-mail: aravindhanpresidency@gmail.com

In the title compound, C28H22O6, the chromeno ring system is almost planar, with a dihedral angle between the mean planes of the pyran and benzene rings of 1.87 (8)°. The pyran ring bearing the methylphenyl substituent has a half-chair conformation while the other pyran ring has an envelope conformation with the tetrasubstituted C atom as the flap. The benzene ring of the chromeno ring system is inclined to the benzene ring fused to the latter pyran ring by 74.66 (9)°. These aromatic rings are inclined to the 4-methylphenyl ring by 52.67 (9) and 66.63 (10)°, respectively. In the crystal, molecules are linked via C-H...O hydrogen bonds, forming a two-dimensional network parallel to the bc plane.

Related literature

For the biological importance of 4H-chromene derivatives, see: Cai et al. (2006[Cai, S. X., Drewe, J. & Kasibhatla, S. (2006). Curr. Med. Chem. 13, 2627-2644.]); Cai (2007[Cai, S. X. (2007). Recent Patents Anticancer Drug Discov. 2, 79-101.], 2008[Cai, S. X. (2008). Bioorg. Med. Chem. Lett. 18, 603-607.]); Gabor (1988[Gabor, M. (1988). The Pharmacology of Benzopyrone Derivatives and Related Compounds, pp. 91-126. Budapest: Akademiai Kiado.]); Brooks (1998[Brooks, G. T. (1998). Pestic. Sci. 22, 41-50.]); Valenti et al. (1993[Valenti, P., Da Re, P., Rampa, A., Montanari, P., Carrara, M. & Cima, L. (1993). Anticancer Drug. Des. 8, 349-360.]); Hyana & Saimoto (1987[Hyana, T. & Saimoto, H. (1987). Jpn Patent JP 621 812 768.]); Tang et al. (2007[Tang, Q.-G., Wu, W.-Y., He, W., Sun, H.-S. & Guo, C. (2007). Acta Cryst. E63, o1437-o1438.]).

[Scheme 1]

Experimental

Crystal data

  • C28H22O6

  • Mr = 454.46

  • Monoclinic, P 21 /c

  • a = 9.526 (5) Å

  • b = 10.711 (5) Å

  • c = 21.975 (5) Å

  • [beta] = 97.397 (5)°

  • V = 2223.5 (16) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 293 K

  • 0.32 × 0.20 × 0.10 mm
Data collection

  • Bruker APEXII CCD 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 = 0.992

  • 22624 measured reflections

  • 4741 independent reflections

  • 3251 reflections with I > 2[sigma](I)

  • Rint = 0.028
Refinement

  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.133

  • S = 1.01

  • 4741 reflections

  • 324 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C4-H4...O5i 0.93 2.35 3.209 (2) 153
C21-H21A...O5ii 0.96 2.43 3.285 (3) 148
Symmetry codes: (i) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (ii) [-x+1, y+{\script{1\over 2}}, -z-{\script{1\over 2}}].

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: SU2541 ).

Acknowledgements

SA and VS thank the UGC, India, for financial support. The authors thank Dr Babu Varghese, Senior Scientific Officer, SAIF, IIT, Chennai, India, for the data collection.

References

Brooks, G. T. (1998). Pestic. Sci. 22, 41-50.  [CrossRef]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cai, S. X. (2007). Recent Patents Anticancer Drug Discov. 2, 79-101.
Cai, S. X. (2008). Bioorg. Med. Chem. Lett. 18, 603-607.  [PubMed]
Cai, S. X., Drewe, J. & Kasibhatla, S. (2006). Curr. Med. Chem. 13, 2627-2644.  [ISI] [PubMed] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gabor, M. (1988). The Pharmacology of Benzopyrone Derivatives and Related Compounds, pp. 91-126. Budapest: Akademiai Kiado.
Hyana, T. & Saimoto, H. (1987). Jpn Patent JP 621 812 768.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Tang, Q.-G., Wu, W.-Y., He, W., Sun, H.-S. & Guo, C. (2007). Acta Cryst. E63, o1437-o1438.  [CSD] [CrossRef] [details]
Valenti, P., Da Re, P., Rampa, A., Montanari, P., Carrara, M. & Cima, L. (1993). Anticancer Drug. Des. 8, 349-360.  [ChemPort] [PubMed]

Acta Cryst (2013). E69, o267-o268   [ doi:10.1107/S1600536813001244 ]

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