Absolute configuration of isovouacapenol C

Fun, H.-K.; Yodsaoue, O.; Karalai, C.; Chantrapromma, S.

doi:10.1107/S1600536810028023

organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Pages o2059-o2060

https://doi.org/10.1107/S1600536810028023

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Absolute configuration of isovouacapenol C

Hoong-Kun Fun,^a ^*‡ Orapun Yodsaoue,^b Chatchanok Karalai ^b and Suchada Chantrapromma ^c §

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^cCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
^*Correspondence e-mail: hkfun@usm.my

(Received 11 July 2010; accepted 14 July 2010; online 17 July 2010)

The title compound, C₂₇H₃₄O₅ {systematic name: (4aR,5R,6R,6aS,7R,11aS,11bR)-4a,6-dihydroxy-4,4,7,11b-tetramethyl-1,2,3,4,4a,5,6,6a,7,11,11a,11b-dodecahydrophenanthro[3,2-b]furan-5-yl benzoate}, is a cassane furanoditerpene, which was isolated from the roots of Caesalpinia pulcherrima. The three cyclohexane rings are trans fused: two of these are in chair conformations with the third in a twisted half-chair conformation, whereas the furan ring is almost planar (r.m.s. deviation = 0.003 Å). An intramolecular C—H⋯O interaction generates an S(6) ring. The absolute configurations of the stereogenic centres at positions 4a, 5, 6, 6a, 7, 11a and 11b are R, R, R, S, R, S and R, respectively. In the crystal, molecules are linked into infinite chains along [010] by O—H⋯O hydrogen bonds. C⋯O [3.306 (2)–3.347 (2) Å] short contacts and C—H⋯π interactions also occur.

Related literature

For ring conformations, see: Cremer & Pople (1975 ). For bond-length data, see: Allen et al. (1987 ). For background to plants in Caesalpiniaceae, cassane furanoditerpenes and their activities, see: Che et al. (1986 ); Jiang et al. (2001 ); Patil et al. (1997 ); Promsawan et al. (2003 ); Ragasa et al. (2002 ); Smitinand & Larson (2001 ); Tewtrakul et al. (2003 ). For related structures, see: Jiang et al. (2001). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₇H₃₄O₅
M_r = 438.54
Monoclinic, P 2₁
a = 11.6236 (7) Å
b = 8.0871 (5) Å
c = 12.4193 (7) Å
β = 98.194 (3)°
V = 1155.51 (12) Å³
Z = 2
Cu Kα radiation
μ = 0.69 mm⁻¹
T = 100 K
0.40 × 0.26 × 0.16 mm

Data collection

Bruker APEX DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.772, T_max = 0.896
23749 measured reflections
3328 independent reflections
3237 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.077
S = 1.05
3328 reflections
289 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.26 e Å⁻³
Absolute structure: Flack (1983 ), 1365 Friedel pairs
Flack parameter: 0.07 (17)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C12–C16/O1 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H1O5⋯O1ⁱ	0.85 (2)	2.27 (3)	2.9814 (19)	141 (2)
C19—H19C⋯O3	0.96	2.37	3.052 (2)	128
C3—H3A⋯Cg1ⁱⁱ	0.97	2.86	3.805 (2)	166
Symmetry codes: (i) x, y-1, z; (ii) $[-x+2, y-{\script{1\over 2}}, -z+2]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810028023/hb5551sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810028023/hb5551Isup2.hkl

checkCIF report

Comment top

The plants in Caesalpiniaceae are rich sources of cassane furanoditerpenes. The extracts from plants in this family have been found to possess bioactivities such as antiviral (Jiang et al., 2001), antitumor (Che et al., 1986) and HIV-1 protease inhibitory (Tewtrakul et al., 2003) properties. Caesalpinia pulcherrima (L.) Swartz, locally known as "Hang Nok Yung Thai" (Smitinand & Larson, 2001) is a large perennial shrub or small tree that is widely distributed in tropical areas. The plant has been used for ornamental (Smitinand & Larson, 2001), abortifacient and emmenagogue purposes. Isolated compounds from C. pulcherrima exhibits potential fertility regulating, antitumor (Che et al., 1986), antibacterial, antifungal (Ragasa et al., 2002) and anti-tubercular activities (Promsawan et al., 2003). These compounds are also active against DNA repair-deficient yeast mutant (Patil et al., 1997). In the course of our research of chemical constituents and bioactive compounds from the roots of C. pulcherrima which were collected from Songkhla province in the southern part of Thailand, the title cassane furanoditerpene (I), also known as isovouacapenol C (Ragasa et al., 2002) or 6β-cinnamoyl-7β-hydroxyvouacapen-5α-ol (Promsawan et al., 2003), was isolated. The previous reports showed that (I) exhibits moderate antimicrobial (Ragasa et al., 2002) and cytotoxic activities (Promsawan et al., 2003). The absolute configuration of (I) was determined by making use of the anomalous scattering of Cu Kα X-radiation with the Flack parameter being refined to 0.07 (17). We report herein the crystal structure of (I).

Fig. 1 shows that the molecule of (I) is constructed from the fusion of three cyclohexane rings and a furan ring. The three cyclohexane rings are trans-fused. Two cyclohexane rings A and B are in standard chair conformations whereas ring C adopts twisted half-chair conformation with the puckered C8 and C9 atoms having the maximum deviation of -0.306 (1) and 0.280 (2) Å, respectively from the best plane of the remaining four atoms (C11–C14) and with the puckering parameters Q = 0.4532 (17) Å and θ = 47.1 (2)° and φ = 23.0 (3)° (Cremer & Pople, 1975). The furan ring (C12/C13/C15/C16/O1) is planar (rms 0.001 (2) Å). Atoms of the benzoate moiety (C21–C27/O3/O4) lie on the same plane with the rms 0.009 (2) Å. The orientation of the benzoate group is described by the torsion angles C21–O3–C6–C5 = 136.98 (16)° and C21–O3–C6–C7 = -99.22 (17)°. The bond angles around C12 and C13 atoms are indicative of sp² hybridization for these atoms and the bond length of 1.344 (3) Å confirmed the C12 ═C13 bond. The bond distances in (I) are within normal ranges (Allen et al., 1987) and comparable with the related structures which are caesalmin C, D, E, F and G (Jiang et al., 2001). The absolute configuration at positions 4a, 5, 6, 6a, 7, 11a and 11b of the isovouacapenol C or atoms C5, C6, C7, C8, C14, C9 and C10 were R,R,R,S,R,S,R configurations.

The crystal packing of (I) is stabilized by intermolecular O—H···O hydrogen bonds (Table 1). The molecules are linked into infinite one dimensional chains along the [010] through O5—H1O5···O1 hydrogen bond (Fig. 2 and Table 1). C···O [3.306 (2)-3.347 (2) Å] short contacts and C—H···π interactions were also observed (Table 1); Cg₁ is the centroid of the C12/C13/C15/C16/O1 ring.

Related literature top

For ring conformations, see: Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987). For background to plants in Caesalpiniaceae, cassane furanoditerpenes and their activity, see: Che et al. (1986); Jiang et al. (2001); Patil et al. (1997); Promsawan et al. (2003); Ragasa et al. (2002); Smitinand & Larson (2001); Tewtrakul et al. (2003). For related structures, see: Jiang et al. (2001). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986).

Experimental top

The air-dried roots of C. pulcherrima (6.3 kg) were extracted with CH₂Cl₂ (2 x 2.5 L) for 5 days at room temperature. The combined extracts were concentrated under reduced pressure to afford a dark brownish extract (75.3 g) which was further purified by quick column chromatography (QCC) over silica gel using hexane as eluent and increasing polarity with EtOAc and MeOH to afford 16 fractions (F1-F16). Fraction F4 was then concentrated under reduced pressure to yield the title compound as white solid (10.0 g). Colorless block-shaped single crystals of the compound (I) were recrystallized from CH₂Cl₂ by the slow evaporation of the solvent at room temperature after several days, Mp. 389-391 K.

Structure description top

For ring conformations, see: Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987). For background to plants in Caesalpiniaceae, cassane furanoditerpenes and their activity, see: Che et al. (1986); Jiang et al. (2001); Patil et al. (1997); Promsawan et al. (2003); Ragasa et al. (2002); Smitinand & Larson (2001); Tewtrakul et al. (2003). For related structures, see: Jiang et al. (2001). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986).

Computing details top

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

Figures top

	Fig. 1. The structure of (I), showing 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of (I) viewed along the c axis, showing one dimensional chains along [010]. Hydrogen bonds are shown as dashed lines.

(4aR,5R,6R,6aS,7R,11aS,11bR)- 4a,6-dihydroxy-4,4,7,11b-tetramethyl-1,2,3,4,4a,5,6,6a,7,11,11a,11b- dodecahydrophenanthro[3,2-b]furan-5-yl benzoate top

Crystal data top

C₂₇H₃₄O₅	F(000) = 472
M_r = 438.54	D_x = 1.260 Mg m⁻³
Monoclinic, P2₁	Melting point = 389–391 K
Hall symbol: P 2yb	Cu Kα radiation, λ = 1.54178 Å
a = 11.6236 (7) Å	Cell parameters from 3328 reflections
b = 8.0871 (5) Å	θ = 3.6–63.0°
c = 12.4193 (7) Å	µ = 0.69 mm⁻¹
β = 98.194 (3)°	T = 100 K
V = 1155.51 (12) Å³	Block, colorless
Z = 2	0.40 × 0.26 × 0.16 mm

Data collection top

Bruker APEX DUO CCD diffractometer	3328 independent reflections
Radiation source: sealed tube	3237 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
φ and ω scans	θ_max = 63.0°, θ_min = 3.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
T_min = 0.772, T_max = 0.896	k = −9→7
23749 measured reflections	l = −14→13

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.077	w = 1/[σ²(F_o²) + (0.0405P)² + 0.2626P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
3328 reflections	Δρ_max = 0.26 e Å⁻³
289 parameters	Δρ_min = −0.26 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1365 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.07 (17)

Crystal data top

C₂₇H₃₄O₅	V = 1155.51 (12) Å³
M_r = 438.54	Z = 2
Monoclinic, P2₁	Cu Kα radiation
a = 11.6236 (7) Å	µ = 0.69 mm⁻¹
b = 8.0871 (5) Å	T = 100 K
c = 12.4193 (7) Å	0.40 × 0.26 × 0.16 mm
β = 98.194 (3)°

Data collection top

Bruker APEX DUO CCD diffractometer	3328 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3237 reflections with I > 2σ(I)
T_min = 0.772, T_max = 0.896	R_int = 0.037
23749 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.077	Δρ_max = 0.26 e Å⁻³
S = 1.05	Δρ_min = −0.26 e Å⁻³
3328 reflections	Absolute structure: Flack (1983), 1365 Friedel pairs
289 parameters	Absolute structure parameter: 0.07 (17)
1 restraint

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.72763 (10)	0.79601 (16)	0.98396 (10)	0.0293 (3)
O2	1.00416 (11)	0.14126 (17)	0.87430 (10)	0.0289 (3)
H1O2	1.074 (2)	0.170 (3)	0.8862 (19)	0.053 (8)*
O3	0.77060 (10)	0.12442 (16)	0.64968 (9)	0.0277 (3)
O4	0.73247 (15)	−0.1497 (2)	0.63427 (14)	0.0558 (5)
O5	0.65515 (11)	0.06283 (18)	0.82285 (11)	0.0305 (3)
H1O5	0.666 (2)	−0.039 (4)	0.839 (2)	0.064 (9)*
C1	1.05196 (15)	0.4722 (2)	0.79744 (15)	0.0294 (4)
H1A	1.0406	0.5910	0.7942	0.035*
H1B	1.0862	0.4444	0.8711	0.035*
C2	1.13691 (16)	0.4242 (3)	0.71969 (17)	0.0366 (5)
H2A	1.1075	0.4634	0.6472	0.044*
H2B	1.2111	0.4775	0.7426	0.044*
C3	1.15455 (16)	0.2376 (3)	0.71644 (17)	0.0362 (5)
H3A	1.1915	0.2007	0.7873	0.043*
H3B	1.2066	0.2125	0.6642	0.043*
C4	1.04021 (15)	0.1404 (3)	0.68549 (15)	0.0290 (4)
C5	0.95342 (15)	0.1960 (2)	0.76622 (14)	0.0248 (4)
C6	0.83929 (14)	0.0968 (2)	0.75469 (14)	0.0246 (4)
H6A	0.8589	−0.0210	0.7607	0.030*
C7	0.76787 (14)	0.1395 (2)	0.84429 (13)	0.0241 (4)
H7A	0.8081	0.0951	0.9129	0.029*
C8	0.74771 (14)	0.3233 (2)	0.85970 (14)	0.0218 (4)
H8A	0.6980	0.3625	0.7943	0.026*
C9	0.86259 (14)	0.4231 (2)	0.86921 (14)	0.0225 (4)
H9A	0.9111	0.3876	0.9363	0.027*
C10	0.93235 (15)	0.3867 (2)	0.77260 (14)	0.0239 (4)
C11	0.84125 (15)	0.6107 (2)	0.87951 (15)	0.0274 (4)
H11A	0.9126	0.6649	0.9112	0.033*
H11B	0.8171	0.6578	0.8080	0.033*
C12	0.74973 (14)	0.6380 (2)	0.94925 (14)	0.0251 (4)
C13	0.67533 (14)	0.5290 (2)	0.98321 (15)	0.0237 (4)
C14	0.67929 (15)	0.3493 (2)	0.95730 (14)	0.0250 (4)
H14A	0.5992	0.3129	0.9341	0.030*
C15	0.60120 (15)	0.6225 (2)	1.04398 (14)	0.0288 (4)
H15A	0.5411	0.5813	1.0783	0.035*
C16	0.63540 (16)	0.7802 (3)	1.04160 (16)	0.0313 (4)
H16A	0.6015	0.8674	1.0744	0.038*
C17	0.72635 (18)	0.2509 (2)	1.05976 (15)	0.0336 (5)
H17A	0.6865	0.2843	1.1188	0.050*
H17B	0.8080	0.2718	1.0785	0.050*
H17C	0.7139	0.1350	1.0461	0.050*
C18	1.06580 (18)	−0.0460 (3)	0.69936 (17)	0.0389 (5)
H18A	1.1315	−0.0740	0.6641	0.058*
H18B	0.9992	−0.1080	0.6672	0.058*
H18C	1.0826	−0.0720	0.7754	0.058*
C19	1.00152 (17)	0.1669 (3)	0.56272 (15)	0.0369 (5)
H19A	1.0538	0.1099	0.5223	0.055*
H19B	1.0024	0.2830	0.5465	0.055*
H19C	0.9243	0.1245	0.5430	0.055*
C20	0.86451 (16)	0.4592 (2)	0.66677 (14)	0.0273 (4)
H20A	0.8826	0.5745	0.6617	0.041*
H20B	0.7826	0.4463	0.6678	0.041*
H20C	0.8863	0.4017	0.6051	0.041*
C21	0.72050 (17)	−0.0116 (3)	0.59848 (17)	0.0360 (5)
C22	0.65118 (16)	0.0302 (3)	0.49182 (17)	0.0376 (5)
C23	0.63903 (19)	0.1895 (3)	0.45270 (17)	0.0479 (6)
H23A	0.6747	0.2767	0.4935	0.058*
C24	0.5734 (2)	0.2196 (4)	0.35231 (19)	0.0622 (5)
H24A	0.5638	0.3268	0.3255	0.075*
C25	0.5217 (2)	0.0850 (4)	0.2917 (2)	0.0622 (5)
H25A	0.4782	0.1041	0.2240	0.075*
C26	0.5340 (2)	−0.0717 (4)	0.33011 (19)	0.0622 (5)
H26A	0.4992	−0.1592	0.2891	0.075*
C27	0.59853 (17)	−0.1005 (3)	0.43053 (18)	0.0481 (6)
H27A	0.6069	−0.2078	0.4574	0.058*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0331 (6)	0.0197 (7)	0.0365 (7)	−0.0005 (5)	0.0095 (5)	−0.0016 (5)
O2	0.0268 (7)	0.0338 (8)	0.0243 (6)	0.0014 (6)	−0.0022 (5)	0.0040 (6)
O3	0.0287 (6)	0.0291 (7)	0.0236 (6)	−0.0015 (5)	−0.0019 (5)	−0.0036 (5)
O4	0.0678 (11)	0.0314 (11)	0.0606 (10)	−0.0050 (8)	−0.0172 (8)	−0.0079 (8)
O5	0.0286 (7)	0.0240 (8)	0.0393 (8)	−0.0063 (5)	0.0060 (6)	0.0004 (6)
C1	0.0276 (9)	0.0312 (12)	0.0305 (10)	−0.0040 (8)	0.0079 (8)	−0.0014 (8)
C2	0.0291 (9)	0.0439 (14)	0.0392 (12)	−0.0084 (9)	0.0130 (8)	−0.0051 (9)
C3	0.0263 (9)	0.0469 (14)	0.0369 (11)	0.0003 (9)	0.0097 (8)	−0.0052 (9)
C4	0.0288 (9)	0.0301 (11)	0.0288 (9)	0.0044 (8)	0.0065 (7)	−0.0029 (8)
C5	0.0248 (9)	0.0301 (11)	0.0185 (9)	0.0028 (7)	−0.0005 (7)	0.0022 (7)
C6	0.0281 (9)	0.0213 (11)	0.0232 (9)	−0.0003 (7)	−0.0010 (7)	−0.0006 (7)
C7	0.0243 (8)	0.0217 (10)	0.0252 (9)	−0.0029 (7)	−0.0002 (7)	0.0013 (8)
C8	0.0229 (8)	0.0207 (10)	0.0218 (9)	0.0000 (7)	0.0026 (7)	0.0023 (7)
C9	0.0234 (8)	0.0242 (10)	0.0194 (8)	−0.0011 (7)	0.0016 (6)	0.0020 (7)
C10	0.0251 (9)	0.0263 (11)	0.0211 (9)	−0.0026 (7)	0.0058 (7)	0.0006 (7)
C11	0.0306 (9)	0.0247 (11)	0.0281 (9)	−0.0065 (8)	0.0092 (7)	0.0004 (8)
C12	0.0266 (9)	0.0224 (10)	0.0257 (9)	0.0011 (8)	0.0016 (7)	0.0002 (8)
C13	0.0220 (9)	0.0233 (11)	0.0255 (9)	0.0016 (7)	0.0027 (7)	0.0019 (7)
C14	0.0220 (8)	0.0250 (11)	0.0282 (9)	−0.0036 (7)	0.0043 (7)	0.0006 (8)
C15	0.0246 (8)	0.0290 (12)	0.0337 (10)	0.0013 (8)	0.0074 (7)	0.0017 (8)
C16	0.0300 (9)	0.0266 (12)	0.0393 (11)	0.0047 (8)	0.0117 (8)	−0.0020 (8)
C17	0.0486 (11)	0.0251 (12)	0.0291 (10)	0.0025 (8)	0.0127 (9)	0.0047 (8)
C18	0.0398 (11)	0.0367 (13)	0.0405 (12)	0.0101 (9)	0.0069 (9)	−0.0042 (9)
C19	0.0415 (11)	0.0432 (14)	0.0281 (10)	0.0028 (9)	0.0129 (8)	−0.0046 (9)
C20	0.0358 (10)	0.0246 (11)	0.0228 (9)	−0.0011 (8)	0.0088 (7)	0.0029 (7)
C21	0.0319 (10)	0.0379 (14)	0.0370 (11)	−0.0010 (9)	0.0011 (8)	−0.0091 (10)
C22	0.0247 (9)	0.0591 (16)	0.0285 (10)	0.0002 (9)	0.0020 (8)	−0.0113 (10)
C23	0.0408 (12)	0.0675 (19)	0.0327 (12)	0.0012 (11)	−0.0042 (9)	−0.0043 (11)
C24	0.0404 (7)	0.1039 (14)	0.0392 (8)	0.0010 (8)	−0.0052 (6)	−0.0099 (8)
C25	0.0404 (7)	0.1039 (14)	0.0392 (8)	0.0010 (8)	−0.0052 (6)	−0.0099 (8)
C26	0.0404 (7)	0.1039 (14)	0.0392 (8)	0.0010 (8)	−0.0052 (6)	−0.0099 (8)
C27	0.0267 (10)	0.0698 (18)	0.0466 (13)	−0.0034 (10)	0.0011 (9)	−0.0195 (12)

Geometric parameters (Å, º) top

O1—C16	1.377 (2)	C11—C12	1.481 (2)
O1—C12	1.384 (2)	C11—H11A	0.9700
O2—C5	1.456 (2)	C11—H11B	0.9700
O2—H1O2	0.84 (3)	C12—C13	1.344 (3)
O3—C21	1.359 (2)	C13—C15	1.438 (3)
O3—C6	1.446 (2)	C13—C14	1.490 (3)
O4—C21	1.203 (3)	C14—C17	1.534 (3)
O5—C7	1.440 (2)	C14—H14A	0.9800
O5—H1O5	0.85 (3)	C15—C16	1.338 (3)
C1—C2	1.526 (2)	C15—H15A	0.9300
C1—C10	1.544 (2)	C16—H16A	0.9300
C1—H1A	0.9700	C17—H17A	0.9600
C1—H1B	0.9700	C17—H17B	0.9600
C2—C3	1.524 (3)	C17—H17C	0.9600
C2—H2A	0.9700	C18—H18A	0.9600
C2—H2B	0.9700	C18—H18B	0.9600
C3—C4	1.545 (3)	C18—H18C	0.9600
C3—H3A	0.9700	C19—H19A	0.9600
C3—H3B	0.9700	C19—H19B	0.9600
C4—C18	1.541 (3)	C19—H19C	0.9600
C4—C19	1.542 (3)	C20—H20A	0.9600
C4—C5	1.586 (2)	C20—H20B	0.9600
C5—C6	1.539 (2)	C20—H20C	0.9600
C5—C10	1.565 (3)	C21—C22	1.488 (3)
C6—C7	1.520 (2)	C22—C23	1.377 (3)
C6—H6A	0.9800	C22—C27	1.392 (3)
C7—C8	1.522 (3)	C23—C24	1.387 (3)
C7—H7A	0.9800	C23—H23A	0.9300
C8—C9	1.550 (2)	C24—C25	1.409 (4)
C8—C14	1.556 (2)	C24—H24A	0.9300
C8—H8A	0.9800	C25—C26	1.355 (4)
C9—C11	1.546 (3)	C25—H25A	0.9300
C9—C10	1.569 (2)	C26—C27	1.381 (3)
C9—H9A	0.9800	C26—H26A	0.9300
C10—C20	1.548 (2)	C27—H27A	0.9300

C16—O1—C12	105.61 (14)	C12—C11—H11B	109.8
C5—O2—H1O2	109.4 (17)	C9—C11—H11B	109.8
C21—O3—C6	116.21 (15)	H11A—C11—H11B	108.2
C7—O5—H1O5	105.5 (18)	C13—C12—O1	110.58 (15)
C2—C1—C10	113.90 (15)	C13—C12—C11	129.30 (17)
C2—C1—H1A	108.8	O1—C12—C11	120.04 (15)
C10—C1—H1A	108.8	C12—C13—C15	106.26 (16)
C2—C1—H1B	108.8	C12—C13—C14	122.06 (16)
C10—C1—H1B	108.8	C15—C13—C14	131.68 (16)
H1A—C1—H1B	107.7	C13—C14—C17	110.19 (15)
C3—C2—C1	111.70 (17)	C13—C14—C8	109.57 (14)
C3—C2—H2A	109.3	C17—C14—C8	114.49 (15)
C1—C2—H2A	109.3	C13—C14—H14A	107.4
C3—C2—H2B	109.3	C17—C14—H14A	107.4
C1—C2—H2B	109.3	C8—C14—H14A	107.4
H2A—C2—H2B	107.9	C16—C15—C13	106.71 (16)
C2—C3—C4	113.34 (16)	C16—C15—H15A	126.6
C2—C3—H3A	108.9	C13—C15—H15A	126.6
C4—C3—H3A	108.9	C15—C16—O1	110.84 (16)
C2—C3—H3B	108.9	C15—C16—H16A	124.6
C4—C3—H3B	108.9	O1—C16—H16A	124.6
H3A—C3—H3B	107.7	C14—C17—H17A	109.5
C18—C4—C19	105.75 (16)	C14—C17—H17B	109.5
C18—C4—C3	108.93 (16)	H17A—C17—H17B	109.5
C19—C4—C3	107.13 (16)	C14—C17—H17C	109.5
C18—C4—C5	109.68 (16)	H17A—C17—H17C	109.5
C19—C4—C5	117.61 (15)	H17B—C17—H17C	109.5
C3—C4—C5	107.49 (15)	C4—C18—H18A	109.5
O2—C5—C6	99.09 (14)	C4—C18—H18B	109.5
O2—C5—C10	107.37 (14)	H18A—C18—H18B	109.5
C6—C5—C10	112.28 (14)	C4—C18—H18C	109.5
O2—C5—C4	106.62 (13)	H18A—C18—H18C	109.5
C6—C5—C4	114.27 (15)	H18B—C18—H18C	109.5
C10—C5—C4	115.46 (15)	C4—C19—H19A	109.5
O3—C6—C7	109.65 (13)	C4—C19—H19B	109.5
O3—C6—C5	111.17 (14)	H19A—C19—H19B	109.5
C7—C6—C5	111.53 (14)	C4—C19—H19C	109.5
O3—C6—H6A	108.1	H19A—C19—H19C	109.5
C7—C6—H6A	108.1	H19B—C19—H19C	109.5
C5—C6—H6A	108.1	C10—C20—H20A	109.5
O5—C7—C6	110.15 (14)	C10—C20—H20B	109.5
O5—C7—C8	106.96 (14)	H20A—C20—H20B	109.5
C6—C7—C8	115.08 (14)	C10—C20—H20C	109.5
O5—C7—H7A	108.1	H20A—C20—H20C	109.5
C6—C7—H7A	108.1	H20B—C20—H20C	109.5
C8—C7—H7A	108.1	O4—C21—O3	124.00 (18)
C7—C8—C9	111.82 (13)	O4—C21—C22	124.02 (19)
C7—C8—C14	109.57 (14)	O3—C21—C22	111.97 (19)
C9—C8—C14	113.63 (13)	C23—C22—C27	120.2 (2)
C7—C8—H8A	107.2	C23—C22—C21	122.82 (19)
C9—C8—H8A	107.2	C27—C22—C21	117.0 (2)
C14—C8—H8A	107.2	C22—C23—C24	119.8 (2)
C11—C9—C8	111.75 (14)	C22—C23—H23A	120.1
C11—C9—C10	110.75 (14)	C24—C23—H23A	120.1
C8—C9—C10	112.18 (14)	C23—C24—C25	118.9 (3)
C11—C9—H9A	107.3	C23—C24—H24A	120.6
C8—C9—H9A	107.3	C25—C24—H24A	120.6
C10—C9—H9A	107.3	C26—C25—C24	121.3 (2)
C1—C10—C20	109.58 (15)	C26—C25—H25A	119.4
C1—C10—C5	107.96 (14)	C24—C25—H25A	119.4
C20—C10—C5	113.24 (15)	C25—C26—C27	119.5 (3)
C1—C10—C9	108.18 (14)	C25—C26—H26A	120.2
C20—C10—C9	108.77 (14)	C27—C26—H26A	120.2
C5—C10—C9	108.99 (14)	C26—C27—C22	120.4 (3)
C12—C11—C9	109.39 (14)	C26—C27—H27A	119.8
C12—C11—H11A	109.8	C22—C27—H27A	119.8
C9—C11—H11A	109.8

C10—C1—C2—C3	−55.8 (2)	C6—C5—C10—C9	56.19 (18)
C1—C2—C3—C4	56.5 (2)	C4—C5—C10—C9	−170.43 (13)
C2—C3—C4—C18	−172.61 (16)	C11—C9—C10—C1	62.08 (18)
C2—C3—C4—C19	73.4 (2)	C8—C9—C10—C1	−172.31 (14)
C2—C3—C4—C5	−53.8 (2)	C11—C9—C10—C20	−56.87 (18)
C18—C4—C5—O2	52.99 (19)	C8—C9—C10—C20	68.74 (18)
C19—C4—C5—O2	173.81 (17)	C11—C9—C10—C5	179.23 (13)
C3—C4—C5—O2	−65.30 (19)	C8—C9—C10—C5	−55.16 (18)
C18—C4—C5—C6	−55.39 (19)	C8—C9—C11—C12	38.72 (19)
C19—C4—C5—C6	65.4 (2)	C10—C9—C11—C12	164.58 (13)
C3—C4—C5—C6	−173.68 (15)	C16—O1—C12—C13	0.04 (18)
C18—C4—C5—C10	172.14 (15)	C16—O1—C12—C11	177.07 (15)
C19—C4—C5—C10	−67.0 (2)	C9—C11—C12—C13	−13.3 (3)
C3—C4—C5—C10	53.85 (19)	C9—C11—C12—O1	170.25 (14)
C21—O3—C6—C7	−99.22 (17)	O1—C12—C13—C15	−0.31 (19)
C21—O3—C6—C5	136.98 (16)	C11—C12—C13—C15	−176.98 (17)
O2—C5—C6—O3	−178.22 (14)	O1—C12—C13—C14	179.95 (15)
C10—C5—C6—O3	68.69 (18)	C11—C12—C13—C14	3.3 (3)
C4—C5—C6—O3	−65.27 (18)	C12—C13—C14—C17	108.18 (19)
O2—C5—C6—C7	59.06 (17)	C15—C13—C14—C17	−71.5 (2)
C10—C5—C6—C7	−54.03 (19)	C12—C13—C14—C8	−18.7 (2)
C4—C5—C6—C7	172.01 (15)	C15—C13—C14—C8	161.67 (17)
O3—C6—C7—O5	48.39 (19)	C7—C8—C14—C13	171.36 (14)
C5—C6—C7—O5	171.97 (14)	C9—C8—C14—C13	45.48 (19)
O3—C6—C7—C8	−72.59 (18)	C7—C8—C14—C17	47.00 (19)
C5—C6—C7—C8	50.99 (19)	C9—C8—C14—C17	−78.89 (19)
O5—C7—C8—C9	−172.92 (13)	C12—C13—C15—C16	0.5 (2)
C6—C7—C8—C9	−50.21 (18)	C14—C13—C15—C16	−179.83 (19)
O5—C7—C8—C14	60.18 (16)	C13—C15—C16—O1	−0.4 (2)
C6—C7—C8—C14	−177.12 (13)	C12—O1—C16—C15	0.3 (2)
C7—C8—C9—C11	177.36 (14)	C6—O3—C21—O4	−1.7 (3)
C14—C8—C9—C11	−57.96 (18)	C6—O3—C21—C22	179.54 (14)
C7—C8—C9—C10	52.30 (18)	O4—C21—C22—C23	−179.9 (2)
C14—C8—C9—C10	176.98 (14)	O3—C21—C22—C23	−1.1 (3)
C2—C1—C10—C20	−71.1 (2)	O4—C21—C22—C27	−0.6 (3)
C2—C1—C10—C5	52.7 (2)	O3—C21—C22—C27	178.17 (17)
C2—C1—C10—C9	170.49 (16)	C27—C22—C23—C24	0.5 (3)
O2—C5—C10—C1	65.60 (17)	C21—C22—C23—C24	179.76 (19)
C6—C5—C10—C1	173.47 (14)	C22—C23—C24—C25	−0.8 (3)
C4—C5—C10—C1	−53.14 (18)	C23—C24—C25—C26	0.6 (4)
O2—C5—C10—C20	−172.90 (13)	C24—C25—C26—C27	0.0 (4)
C6—C5—C10—C20	−65.02 (18)	C25—C26—C27—C22	−0.3 (3)
C4—C5—C10—C20	68.36 (18)	C23—C22—C27—C26	0.1 (3)
O2—C5—C10—C9	−51.69 (17)	C21—C22—C27—C26	−179.21 (19)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C12–C16/O1 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O5—H1O5···O1ⁱ	0.85 (2)	2.27 (3)	2.9814 (19)	141 (2)
C19—H19C···O3	0.96	2.37	3.052 (2)	128
C3—H3A···Cg1ⁱⁱ	0.97	2.86	3.805 (2)	166

Symmetry codes: (i) x, y−1, z; (ii) −x+2, y−1/2, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₇H₃₄O₅
M_r	438.54
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	100
a, b, c (Å)	11.6236 (7), 8.0871 (5), 12.4193 (7)
β (°)	98.194 (3)
V (Å³)	1155.51 (12)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	0.69
Crystal size (mm)	0.40 × 0.26 × 0.16

Data collection
Diffractometer	Bruker APEX DUO CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.772, 0.896
No. of measured, independent and observed [I > 2σ(I)] reflections	23749, 3328, 3237
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.578

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.077, 1.05
No. of reflections	3328
No. of parameters	289
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.26
Absolute structure	Flack (1983), 1365 Friedel pairs
Absolute structure parameter	0.07 (17)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C12–C16/O1 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O5—H1O5···O1ⁱ	0.85 (2)	2.27 (3)	2.9814 (19)	141 (2)
C19—H19C···O3	0.96	2.37	3.052 (2)	128
C3—H3A···Cg1ⁱⁱ	0.97	2.86	3.805 (2)	166

Symmetry codes: (i) x, y−1, z; (ii) −x+2, y−1/2, −z+2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Additional correspondence author, e-mail: suchada.c@psu.ac.th. Thomson Reuters ResearcherID: A-5085-2009.

Acknowledgements

OY thanks the Office of the Higher Education Commission, Thailand, for financial support by a grant fund under the program "Strategic Scholarships for Frontier Research Network for the Joint PhD Program Thai Doctoral Degree". The authors thank the Thailand Research Fund (BRG5280013) and the Prince of Songkla University for financial support. They also thank Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

References

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Volume 66| Part 8| August 2010| Pages o2059-o2060

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