Maleopimaric acid acetic acid solvate

Meng Zhang; Yong-hong Zhou; Xiao-xin Guo; Li-hong Hu

doi:10.1107/S1600536809023745

. 2009 Jun 27;65(Pt 7):o1714. doi: 10.1107/S1600536809023745

Maleopimaric acid acetic acid solvate

Meng Zhang ^a, Yong-hong Zhou ^a,^*, Xiao-xin Guo ^a, Li-hong Hu ^a

PMCID: PMC2969235 PMID: 21582965

Abstract

The title compound, C₂₄H₃₂O₅·C₂H₄O₂, is a derivative of abietic acid. The two fused and unbridged cyclohexane rings have chair conformations and the anhydride ring is planar. Of the other three six-membered rings, two have boat conformations and one has a twist-boat conformation. The crystal structure is stabilized by intermolecular O—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For general background, see: McCoy (2000 ▶); Schweizer et al. (2003 ▶); Savluchinske-Feio et al. (2007 ▶). For the crystal structure of a similar compound, see: Pan et al. (2006 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₄H₃₂O₅·C₂H₄O₂
M _r = 460.55
Orthorhombic,
a = 7.9469 (10) Å
b = 12.7755 (16) Å
c = 24.884 (3) Å
V = 2526.3 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 291 K
0.30 × 0.26 × 0.24 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.97, T _max = 0.98
13853 measured reflections
2837 independent reflections
2432 reflections with I > 2σ(I)
R _int = 0.059

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.110
S = 1.04
2837 reflections
304 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809023745/wn2334sup1.cif

e-65-o1714-sup1.cif^{(26.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809023745/wn2334Isup2.hkl

e-65-o1714-Isup2.hkl^{(139.3KB, 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—H4C⋯O6	0.93	1.70	2.617 (3)	169
O7—H7A⋯O5	0.93	1.76	2.681 (3)	171
C13—H13C⋯O5ⁱ	0.96	2.59	3.137 (5)	117
C26—H26B⋯O1ⁱⁱ	0.96	2.56	3.369 (4)	142

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

Acknowledgments

This work was supported by the President of the Chinese Academy of Forestry Foundation (CAFYBB2008009).

supplementary crystallographic information

Comment

Rosin, a versatile natural resin, possesses a rare combination of many desirable properties and has consequently found innumerable industrial uses in a modified form or in conjunction with other natural or synthetic resins (McCoy, 2000). Abietic type resin acid is the major component of gum rosin, including abietic acid, neoabietic acid, levo-pimaric acid, palustric acid and is a high quality biomass resource in developing chiral new drugs (Schweizer et al., 2003). Abietic acid and its derivatives are readily available hydrophenanthrene compounds which form useful starting materials for the design and synthesis of industrially and physiologically important products (Savluchinske-Feio et al.,2007).

The crystal structure of a similar compound, also a derivative of maleopimaric acid, has already been published (Pan et al., 2006). The molecular structure of the title compound, is shown in Fig. 1. The asymmetric unit consists of two molecules, viz. maleopimaric anhydride and acetic acid. The cyclohexane rings C5, C6, C14–C16, C21 and C16—C21 have typical chair forms. The cyclohexane ring C2–C7 has a slightly distorted twist-boat conformation; the other two six-membered rings adopt boat conformations. The configuration about the C9═C10 bond is Z (Fig. 1), with the H atom and the isopropyl group cis with respect to each other. The bond lengths (Allen et al., 1987) and bond angles exhibit normal values. In the crystal structure, the molecules are linked (Fig.2) by O—H···O and C—H···O intermolecular hydrogen bonds, also by van der Waals forces.

Experimental

Rosin (10.0 g), acetic acid (7 ml), and maleic anhydride (3.0 g) were put into a 50-ml three-necked flask and magnetically stirred; the mixture was stirred for 20 min with power 450w. The solution was put into 5 ml glacial acetic acid and cooled, washed with hot water (10 ml), dried (MgSO₄), and concentrated to dryness. Recrystallization from ethanol afforded the adduct (7.5 g, 50%).