(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; V Sabari; G Sivakumar; M Bakthadoss; S Aravindhan

doi:10.1107/S1600536813001244

. 2013 Jan 19;69(Pt 2):o267–o268. doi: 10.1107/S1600536813001244

(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 Bakthadoss ^c, S Aravindhan ^b,^*

PMCID: PMC3569797 PMID: 23424543

Abstract

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 (2007 ▶, 2008 ▶); Gabor (1988 ▶); Brooks (1998 ▶); Valenti et al. (1993 ▶); Hyana & Saimoto (1987 ▶); Tang et al. (2007 ▶).

Experimental

Crystal data

C₂₈H₂₂O₆
M _r = 454.46
Monoclinic,
a = 9.526 (5) Å
b = 10.711 (5) Å
c = 21.975 (5) Å
β = 97.397 (5)°
V = 2223.5 (16) Å³
Z = 4
Mo Kα radiation
μ = 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 ▶) T _min = 0.972, T _max = 0.992
22624 measured reflections
4741 independent reflections
3251 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.133
S = 1.01
4741 reflections
324 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.16 e Å⁻³

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 Material

Click here for additional data file.^{(24.5KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813001244/su2541sup1.cif

e-69-0o267-sup1.cif^{(24.5KB, cif)}

Click here for additional data file.^{(227.6KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813001244/su2541Isup2.hkl

e-69-0o267-Isup2.hkl^{(227.6KB, hkl)}

Click here for additional data file.^{(29B, cml)}

Supplementary material file. DOI: 10.1107/S1600536813001244/su2541Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

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.

supplementary crystallographic information

Comment

4H-Chromenes are biologically important compounds used as synthetic ligands for drug design and discovery processes. They exhibit numerous biological and pharmacological properties such as anti-viral, anti-fungal, anti-inflammatory, anti-diabetic, cardionthonic, anti-anaphylactic and anti-cancer activity (Cai et al., 2006; Cai, 2007,2008; Gabor, 1988; Brooks, 1998; Valenti et al., 1993; Hyana & Saimoto, 1987; Tang et al., 2007). In view of the growing medicinal importance of 4H-chromene derivatives, the title compound was synthesized and we describe herein its crystal structure.

The molecular structure of the title molecule is illustrated in Fig. 1. The mean plane of pyran ring A and the benzene ring (C1—C6) of the chromeno system are inclined to one another by 1.87 (8) °. Atom O2 deviates by 0.1987 (13) Å from the mean plane of the chromeno ring system (O1,C1—C9). Pyran ring A (O3/C7/C8/C10-C12) has a half-chair conformation while pyran ring B (O4/C10/C12-C15) has an envelope conformation with the tetra-substituted C atom, C12, as the flap. Benzene ring (C1—C6) of the chromeno ring system is inclined to the benzene ring (C14-C19) fused to pyran ring B by 74.66 (9) °. The 4-methylphenyl ring (C22-C27) is inclined to benzene rings (C1-C6) and (C14-C19) 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 lying parallel to the bc plane (Table 1 and Fig. 2).

Experimental

A mixture of (E)-methyl 2-((2-formylphenoxy)methyl)-3-(4-methylphenyl) acrylate (0.308 g, 1 mmol) and 4-hydroxy-2H-chromen-2-one (0.162 g, 1 mmol) was placed in a round bottom flask and melted at 453 K for 1 h. After completion of the reaction as indicated by TLC, the crude product was washed with 5 ml of ethylacetate:hexane mixture (1:49 ratio) which successfully provided the title compound as a colourless solid in 97% yield. Diffraction quality crystals were obtained by slow evaporation of a solution in ethyl acetate.