10a-Hy­droxy-9-(4-meth­oxy­phen­yl)-3,4,5,6,7,8a,9,10a-octa­hydro-1H-xanthene-1,8(2H)-dione

Hoong-Kun Fun; Chin Wei Ooi; B Palakshi Reddy; V Vijayakumar; S Sarveswari

doi:10.1107/S160053681203005X

. 2012 Jul 7;68(Pt 8):o2367–o2368. doi: 10.1107/S160053681203005X

10a-Hydroxy-9-(4-methoxyphenyl)-3,4,5,6,7,8a,9,10a-octahydro-1H-xanthene-1,8(2H)-dione

Hoong-Kun Fun ^a,^*,^‡, Chin Wei Ooi ^a, B Palakshi Reddy ^b, V Vijayakumar ^b, S Sarveswari ^b

PMCID: PMC3414299 PMID: 22904832

Abstract

In the title compound, C₂₀H₂₂O₅, the tetrahydropyran, cyclohexene and cyclohexane rings of the xanthene ring system adopt half-chair, half-boat and chair conformations, respectively. The mean plane of the four roughly planar atoms of the tetrahydropyran ring (r.m.s. deviation = 0.111 Å) forms a dihedral angle of 82.91 (4)° with the methoxybenzene group. In the crystal, molecules are linked via O—H⋯O and C—H⋯O hydrogen bonds into sheets lying parallel to the ac plane. The crystal is further consolidated by weak C—H⋯π interactions.

Related literature

For background to the applications of xanthene, see: Menchen et al. (2003 ▶); Knight & Stephens (1989 ▶). For our previous studies in this area, see: Palakshi Reddy et al. (2010 ▶); Reddy et al. (2009 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For a related structure, see: Loh et al. (2011 ▶). For bond length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₂₀H₂₂O₅
M _r = 342.38
Orthorhombic,
a = 15.7611 (9) Å
b = 18.0089 (11) Å
c = 11.6451 (7) Å
V = 3305.3 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.48 × 0.23 × 0.11 mm

Data collection

Bruker APEX DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.954, T _max = 0.990
97212 measured reflections
7190 independent reflections
6068 reflections with I > 2σ(I)
R _int = 0.045

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.108
S = 1.05
7190 reflections
231 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681203005X/hb6880sup1.cif

e-68-o2367-sup1.cif^{(28.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681203005X/hb6880Isup2.hkl

e-68-o2367-Isup2.hkl^{(351.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681203005X/hb6880Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H1O4⋯O3ⁱ	0.886 (17)	1.935 (17)	2.8156 (8)	172.0 (16)
C12—H12B⋯O4ⁱⁱ	0.99	2.50	3.1879 (9)	126
C12—H12A⋯Cg1ⁱⁱⁱ	0.99	2.78	3.6557 (8)	147
C16—H16A⋯Cg1^iv	0.99	2.78	3.7467 (8)	165

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

Acknowledgments

HKF and CWO thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160). CWO also thanks the Malaysian Goverment and USM for the award of the post of Research Officer under Research University Grant No. 1001/PFIZIK/811160. VV, SS and BPR are grateful to VIT University for providing facilities to carry out research work.

supplementary crystallographic information

Comment

Xanthene derivatives are important heterocyclic compounds: their uses vary from dyes (Menchen et al., 2003) to agricultural bactericides (Knight et al., 1989). In continuation of our earlier interest in 1,4-DHP's and piperidones (Palakshi Reddy et al. 2009; Palakshi Reddy et al. 2010), herein we report the crystal structure of the title compound.

In the title compound (Fig. 1), the xanthene ring system consists of three rings which adopt different conformations. The tetrahydropyran ring (O5/C8/C9/C14/C15/C20) adopts a half chair conformation with the puckering parameters Q = 0.4980 (7) Å, θ = 122.73 (8)°, φ = 104.23 (9)° (Cremer & Pople, 1975). The cyclohexene (C9–C14) and cyclohexane (C15–C20) rings adopt half boat and chair conformations with the puckering parameters Q = 0.4905 (8) Å, θ = 117.37 (9)°, φ = 349.74 (10)° and Q = 0.5575 (8) Å, θ = 176.39 (8)°, φ = 192.6 (13)° (Cremer & Pople, 1975), respectively. The mean plane of the tetrahydropyran ring [r.m.s deviation = 0.111 Å] forms a dihedral angle of 82.91 (4)° with the methoxyphenyl group (C1–C7/O1). The bond lengths and angles are comparable to those in a related structure (Loh et al., 2011).

In the crystal structure (Fig. 2), the molecules are linked via intermolecular O4—H1O4···O3 and C12—H12B···O4 hydrogen bonds (Table 1) into two-dimensional networks parallel to the ac plane. The crystal structure is further consolidated by weak C—H···π interactions (Table 1), involving the centroid of the benzene ring (C2–C7; Cg1).

Experimental

A mixture of 4-methoxybenzaldehyde (1 mol) and 1,3-cyclohexanedione (2 mol) was refluxed in acetonitrile for 3 h. The progress of the reaction was monitored by TLC. After completion of the reaction, it was kept for 2 days for solid formation. The pure product was obtained by recrystallization from acetonitrile in the form of colourless blocks. M.p.: 194–196°C; Yield 70%.