6-[(E)-3,7-Dimethyl­octa-2,6-dien­yl]-5,7-dihydr­oxy-8-(2-methyl­butano­yl)-4-phenyl-2H-chromen-2-one from Mesua kunstleri King (Kosterm)

Gomathi Chan; Khalijah Awang; A Hamid A Hadi; Seik Weng Ng

doi:10.1107/S1600536808018151

. 2008 Jun 25;64(Pt 7):o1332. doi: 10.1107/S1600536808018151

6-[(E)-3,7-Dimethylocta-2,6-dienyl]-5,7-dihydroxy-8-(2-methylbutanoyl)-4-phenyl-2H-chromen-2-one from Mesua kunstleri King (Kosterm)

Gomathi Chan ^a, Khalijah Awang ^a, A Hamid A Hadi ^a, Seik Weng Ng ^a,^*

PMCID: PMC2961863 PMID: 21202956

Abstract

The title compound, C₃₀H₃₄O₅, crystallizes with two symmetry-independent molecules in the asymmetric unit. In the crystal structure, the two independent molecules are disposed about a pseudo-center of inversion. An intramolecular O—H⋯O hydrogen bond is observed in each independent molecule. The crystal structure is stabilized by C—H⋯O hydrogen bonds.

Related literature

For the spectroscopic analysis of the title compound, see: Verotta et al. (2004 ▶).

Experimental

Crystal data

C₃₀H₃₄O₅
M _r = 474.57
Triclinic,
a = 5.6729 (1) Å
b = 13.4350 (3) Å
c = 16.8404 (3) Å
α = 87.550 (1)°
β = 82.243 (1)°
γ = 85.332 (1)°
V = 1266.88 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 (2) K
0.40 × 0.08 × 0.04 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
16336 measured reflections
5783 independent reflections
4459 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.070
wR(F ²) = 0.210
S = 1.04
5783 reflections
645 parameters
65 restraints
H-atom parameters constrained
Δρ_max = 1.21 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808018151/ci2600sup1.cif

e-64-o1332-sup1.cif^{(38KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018151/ci2600Isup2.hkl

e-64-o1332-Isup2.hkl^{(283.1KB, hkl)}

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
O4—H4o⋯O5	0.84	1.70	2.438 (8)	145
O9—H9o⋯O10	0.84	1.71	2.452 (9)	147
C29—H29b⋯O5ⁱ	0.99	2.29	3.115 (10)	140
C32—H32⋯O2ⁱⁱ	0.95	2.43	3.347 (8)	161
C35—H35⋯O2ⁱⁱⁱ	0.95	2.47	3.242 (9)	138
C39—H39⋯O8^iv	0.95	2.55	3.434 (8)	155

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

Acknowledgments

The authors thank the University of Malaya (PPP PS156/2007B) for supporting this study.

supplementary crystallographic information

Comment

The title compound, previously isolated from Mesua ferrea, has been evaluated as a multidrug-resistant antibacterial. The structure was elucidated from spectroscopic measurements (Verotta et al., 2004). Locally, the bark of Mesua kunstleri (King) Kosterm is used for the treatment of dyspepsis and renal diseases. The identical compound is isloated from the bark of this plant; the compound features the common coumarin skeleton, and is an 8-acyl-6-prenyl derivative. The spectroscopic assignment is now confirmed in the crystal structure analysis.

The title compound contains two independent molecules that are disposed over a false center of inversion (Fig. 1). An intramolecular O—H···O hydrogen bond is observed in each independent molecule. The crystal structure is stabilized by C—H···O hydrogen bonds (Table 1).

Experimental

One-and-a-half kg of the bark of Mesua kunstleri King (Kosterm), (Clusiaceae), collected at Hutan Simpanan Rimba Teloi, Kedah, Malaysia [voucher specimen number KL4485], were extracted by maceration in hexane (6 L) for 72 h to yield a gummy residue (103 g). A portion (10 g) was column chromatographed over silica gel (300 g, 40–63 µm) by using hexane-ethyl acetate as eluents to give six fractions. The first fraction (6 g) was further chromatographed over silica gel (180 g, 5–40 µm) by using hexane:ethyl acetate (95:5). The title compound (1.5 g) was eluted with hexane:ethyl acetate (96:4).