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Acta Cryst. (2007). E63, o3958-o3959    [ doi:10.1107/S1600536807041906 ]

Gerontoxanthone I methanol solvate

N. Boonnak, H.-K. Fun, S. Chantrapromma and C. Karalai

Abstract top

A methanol solvate of gerontoxanthone I [systematic name: 4-(1,1-dimethylprop-2-enyl)-1,3,5,6-tetrahydroxy-2-(3-methylbut-2-enyl)-9H-xanthen-9-one methanol solvate], C23H24O6·CH3OH, is reported. Gerontoxanthone I was isolated from the roots of Cratoxylum formosum ssp. pruniflorum. The three rings in the structure are essentially coplanar. The 3-methylbut-2-enyl side chain is equatorially attached to the benzene ring, whereas the 1-methylbut-2-enyl substituent is bisectionally attached to the benzene ring. Intramolecular O-H...O hydrogen bonds generate S(5) and S(6) ring motifs. In the crystal structure, intermolecular O-H...O hydrogen bonds and C-H...O interactions connect the molecules of gerontoxanthone I into chains along the [100] direction. The crystal structure is stabilized by intra- and intermolecular O-H...O hydrogen bonds, weak C-H...O intra- and intermolecular interactions, and C-H...[pi] interactions.

Comment top

Some species of plants in the genus Cratoxylum have been used for the treatment of diuretic, stomachic, and tonic effects (Kitanov et al., 1988), as well as for diarrhea and flatulence (Aderson, 1986). In our ongoing research of bioactive compounds from medicinal plants, the title compound, gerontoxanthone I, was isolated from a dichloromethane extract of the roots of Cratoxylum formosum ssp. pruniflorum, collected from Nhongkai Province in the northeasthern part of Thailand. As the title compound showed strong antibacterial and cytotoxic activities (Boonnak, Karalai, et al., 2006), its X-ray crystal structure was determined in order to gain more information for further SAR (Structure and Activity Relationship) analysis. In our previous studies, we have reported the crystal structures of xanthone and anthraquinone compounds from the roots and barks of this plant (Boonnak et al., 2005; Boonnak, Chantrapromma & Fun, 2006; Boonnak, Karalai et al., 2006; Chantrapromma et al., 2005; 2006; Fun et al., 2006). We report here the crystal structure of the methanol solvate of gerontoxanthone I.

In the title compound (Fig. 1), the xanthone skeleton (rings A, B and C) is essentially planar, the maximum deviation from planarity being 0.043 (2) Å for atom C3. The O2—H2A···O1 and O4—H4A···O3 hydrogen bonds generate S(5) and S(6) ring motifs, respectively (Bernstein et al., 1995) and help to stabilize the planarity of the structure. There are also weak intramolecular C—H···O interactions; C18—H18B···O6 and C19—H19A···O4 generate S(6) and S(5) ring motifs respectively (Table 1).

The orientation of the 3-methylbut-2-enyl [C19–C23] side chain with respect to the benzene ring C is indicated by the torsion angle of C13—C12—C19—C20 = −93.25 (17)°, [90.6 (2)° in the monohydrate compound (Boonnak, Chantrapromma & Fun, 2006)], indicating a (-)-synclinal conformation (Fig. 1). The 1,1-dimethylprop-2-enyl [C14–C18] substituent is attached to the benzene ring at C10 with the torsion angle C9—C10—C14—C15 of −137.06 (17)° [−52.6 (3)° in Boonnak, Chantrapromma & Fun, 2006], indicating a (-)-anticlinal conformation. Bond distances and angles in the title compound are in normal ranges (Allen et al., 1987) and comparable to those reported in the gerontoxanthone I monohydrate (Boonnak, Chantrapromma & Fun, 2006) and other closely related structures (Boonnak et al., 2005; Boonnak, Karalai et al., 2006; Chantrapromma et al., 2005; 2006; Fun et al., 2006). The methanol solvent molecule is also involved in hydrogen bonds (Table 1).

In the crystal packing (Fig. 2), the gerontoxanthone I molecules are linked together into chains along the a axis by the intermolecular O2—H1O2···O4 hydrogen bond (symmetry code: −1 + x, y, z) and weak C19—H19A···O2 interaction (symmetry code: 1 + x, y, z) (Table 1) and are further linked to the methanol molecules by O1—H1O1···O7 (symmetry code: −1 + x, y, −1 + z) and O7—H1O7···O3 (symmetry code: 1 − x, 1 − y, 1 − z) hydrogen bonds (Table 1). This packing is different from the three dimensional crystal packing of the monohydrate compound (Boonnak, Chantrapromma & Fun, 2006). The crystal structure is stabilized by intra- and intermolecular O—H···O hydrogen bonds, weak C—H···O intra- and intramolecular interactions (Table 1). In addition, the molecular packing is further stabilized by a C—H···π interaction between one of the methyl groups of the 3-methylbut-2-enyl side chain and the centroid of the C1–C6 benzene ring (Cg1) (Table 1).

Related literature top

For related literature on hydrogen-bond motifs, see: Bernstein et al. (1995). For related literature on values of bond lengths, see: Allen et al. (1987). For related structures, see, for example: Boonnak et al. (2005); Boonnak, Chantrapromma & Fun (2006); Boonnak, Karalai et al. (2006); Chantrapromma et al. (2005, 2006); Fun et al. (2006). For related literature on bioactivities of xanthones, see, for example: Aderson (1986); Boonnak, Karalai et al. (2006); Kitanov et al. (1988).

Experimental top

Air-dried roots of Cratoxylum formosum ssp. pruniflorum (5.30 kg) were ground and extracted with CH2Cl2 (2x20 l for 2x5 days) at room temperature. The residue obtained after evaporation of the solvent was subjected to quick column chromatography (QCC) on silica gel, using hexane as first eluent and then increasing polarity with EtOAc and acetone, to afford 8 fractions (F1–F8). Fraction F3 was separated by CC with 10% acetone–hexane to give the title compound. Yellow needle-shaped single crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of the solvents from a CHCl3/CH3OH (7:3 v/v) solution after several days (M.p. 452–453 K).

Refinement top

H atoms of the methanol molecule and the H atoms attached to O5 and O7 were located in a difference map. The remaining H atoms were placed in calculated positions with O—H distance of 0.82 Å and C—H distances in the range 0.93–0.97 Å. The Uiso(H) values were constrained to be 1.5Ueq(carrier atom) for hydroxyl and methyl H atoms and 1.2Ueq(carrier atom) for the remaining H atoms. Owing to a large fraction of weak data at higher angles, the 2θ maximum was limited to 50°. A rotating group model was used for the methyl groups.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 1997) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering scheme. Hydrogen bonds are drawn as dashed lines.
[Figure 2] Fig. 2. The crystal packing of the title compound viewed along the b axis. Hydrogen bonds are drawn as dashed lines.
4-(1,1-dimethylprop-2-enyl)-1,3,5,6-tetrahydroxy-2-(3-methylbut-2-enyl)- 9H-xanthen-9-one methanol solvate top
Crystal data top
C23H24O6·CH4OF000 = 912
Mr = 428.46Dx = 1.302 Mg m−3
Monoclinic, P21/cMelting point: 452-453 K
Hall symbol: -P 2ybcMo Kα radiation
λ = 0.71073 Å
a = 10.0411 (8) ÅCell parameters from 3834 reflections
b = 20.1500 (16) Åθ = 2.3–25.0º
c = 12.1807 (7) ŵ = 0.10 mm−1
β = 117.534 (5)ºT = 297 (2) K
V = 2185.4 (3) Å3Needle, yellow
Z = 40.55 × 0.29 × 0.19 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer		3834 independent reflections
Radiation source: fine-focus sealed tube3429 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.018
Detector resolution: 8.33 pixels mm-1θmax = 25.0º
T = 297(2) Kθmin = 2.3º
ω scansh = −11→11
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		k = −23→23
Tmin = 0.950, Tmax = 0.982l = −7→14
11274 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.141  w = 1/[σ2(Fo2) + (0.0853P)2 + 0.4621P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
3834 reflectionsΔρmax = 0.19 e Å−3
296 parametersΔρmin = −0.36 e Å−3
1 restraintExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
C23H24O6·CH4OV = 2185.4 (3) Å3
Mr = 428.46Z = 4
Monoclinic, P21/cMo Kα
a = 10.0411 (8) ŵ = 0.10 mm−1
b = 20.1500 (16) ÅT = 297 (2) K
c = 12.1807 (7) Å0.55 × 0.29 × 0.19 mm
β = 117.534 (5)º
Data collection top
Siemens SMART CCD area-detector
diffractometer		3834 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3429 reflections with I > 2σ(I)
Tmin = 0.950, Tmax = 0.982Rint = 0.018
11274 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0481 restraint
wR(F2) = 0.141H atoms treated by a mixture of
independent and constrained refinement
S = 1.05Δρmax = 0.19 e Å−3
3834 reflectionsΔρmin = −0.36 e Å−3
296 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
xyzUiso*/Ueq
O1−0.16926 (13)0.49056 (7)0.21463 (12)0.0639 (4)
H1O1−0.222 (3)0.5096 (14)0.146 (3)0.096*
O20.02703 (12)0.42552 (7)0.42133 (11)0.0636 (4)
H1O2−0.06230.43330.39720.095*
O30.48730 (12)0.48078 (7)0.25536 (11)0.0570 (3)
O40.73927 (12)0.42967 (6)0.40403 (11)0.0536 (3)
H1O40.67760.45020.34390.080*
O50.77233 (13)0.30854 (7)0.74175 (13)0.0638 (4)
H5A0.727 (3)0.3031 (13)0.789 (3)0.100 (8)*
O60.30754 (11)0.40989 (5)0.47182 (9)0.0449 (3)
O70.6422 (2)0.53884 (12)0.99678 (17)0.0999 (6)
H1O70.595 (5)0.525 (2)0.9244 (17)0.176 (18)*
C10.17612 (17)0.50642 (8)0.18518 (14)0.0453 (4)
H1B0.21050.52480.13290.054*
C20.02873 (17)0.51419 (8)0.15877 (14)0.0472 (4)
H2A−0.03610.53800.08890.057*
C3−0.02461 (16)0.48670 (8)0.23586 (14)0.0459 (4)
C40.07148 (16)0.45290 (8)0.34219 (14)0.0434 (3)
C50.22065 (15)0.44518 (7)0.36748 (13)0.0387 (3)
C60.27565 (16)0.47090 (7)0.29057 (13)0.0395 (3)
C70.43129 (16)0.45928 (7)0.32226 (13)0.0408 (3)
C80.51977 (15)0.42168 (7)0.43328 (13)0.0385 (3)
C90.45495 (15)0.39753 (7)0.50637 (13)0.0381 (3)
C100.53244 (16)0.35998 (7)0.61333 (14)0.0419 (3)
C110.68362 (16)0.34693 (7)0.64363 (14)0.0437 (4)
C120.75637 (15)0.37038 (7)0.57675 (14)0.0407 (3)
C130.67322 (15)0.40703 (7)0.47158 (13)0.0397 (3)
C140.46210 (18)0.32904 (9)0.69122 (16)0.0530 (4)
C150.5654 (2)0.33895 (13)0.82710 (18)0.0704 (6)
H15A0.60290.38160.85140.084*
C160.6087 (3)0.29370 (19)0.9158 (3)0.1141 (12)
H16A0.57460.25020.89670.137*
H16B0.67330.30540.99720.137*
C170.4329 (4)0.25566 (12)0.6555 (3)0.1012 (9)
H17A0.39850.23390.70780.152*
H17B0.52420.23520.66560.152*
H17C0.35770.25190.57060.152*
C180.3143 (2)0.36078 (13)0.67513 (19)0.0753 (6)
H18A0.28790.34260.73530.113*
H18B0.23570.35160.59340.113*
H18C0.32730.40790.68660.113*
C190.92107 (15)0.35478 (7)0.62011 (14)0.0430 (4)
H19A0.96500.38970.59240.052*
H19B0.97300.35430.70990.052*
C200.94472 (16)0.28944 (8)0.57296 (15)0.0456 (4)
H20A0.90670.28600.48760.055*
C211.01301 (18)0.23594 (8)0.63764 (17)0.0533 (4)
C221.0272 (3)0.17404 (10)0.5744 (2)0.0791 (6)
H22A0.98810.18230.48730.119*
H22B0.97150.13870.58690.119*
H22C1.13100.16160.60870.119*
C231.0826 (3)0.23100 (11)0.7756 (2)0.0756 (6)
H23A1.07990.27370.80960.113*
H23B1.18500.21660.80770.113*
H23C1.02770.19950.79810.113*
C240.6202 (7)0.6016 (2)0.9882 (4)0.186 (2)
H24A0.63620.61870.92170.223*
H24B0.68900.62241.06440.223*
H24C0.51900.61070.97220.223*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0327 (6)0.0978 (10)0.0607 (7)0.0177 (6)0.0213 (5)0.0222 (7)
O20.0348 (6)0.0987 (10)0.0647 (8)0.0163 (6)0.0292 (6)0.0302 (7)
O30.0383 (6)0.0864 (9)0.0505 (6)0.0073 (5)0.0240 (5)0.0220 (6)
O40.0333 (5)0.0794 (8)0.0545 (7)0.0092 (5)0.0256 (5)0.0206 (6)
O50.0421 (6)0.0850 (9)0.0676 (8)0.0232 (6)0.0282 (6)0.0380 (7)
O60.0290 (5)0.0620 (6)0.0457 (6)0.0085 (4)0.0189 (5)0.0151 (5)
O70.0808 (11)0.1318 (17)0.0661 (10)0.0343 (11)0.0160 (9)0.0218 (10)
C10.0373 (8)0.0569 (9)0.0414 (8)0.0024 (6)0.0178 (6)0.0067 (7)
C20.0375 (8)0.0566 (9)0.0416 (8)0.0087 (6)0.0133 (6)0.0075 (7)
C30.0311 (7)0.0554 (9)0.0480 (8)0.0067 (6)0.0155 (6)0.0009 (7)
C40.0327 (7)0.0547 (9)0.0456 (8)0.0049 (6)0.0204 (6)0.0047 (6)
C50.0310 (7)0.0444 (7)0.0389 (7)0.0032 (5)0.0147 (6)0.0023 (6)
C60.0323 (7)0.0448 (7)0.0401 (7)0.0011 (6)0.0156 (6)0.0012 (6)
C70.0334 (7)0.0508 (8)0.0398 (7)−0.0001 (6)0.0183 (6)0.0025 (6)
C80.0304 (7)0.0445 (7)0.0412 (8)0.0006 (5)0.0170 (6)0.0015 (6)
C90.0271 (7)0.0451 (8)0.0427 (7)0.0015 (5)0.0166 (6)0.0017 (6)
C100.0336 (7)0.0479 (8)0.0460 (8)0.0021 (6)0.0199 (6)0.0076 (6)
C110.0353 (7)0.0481 (8)0.0469 (8)0.0064 (6)0.0184 (6)0.0095 (6)
C120.0307 (7)0.0447 (8)0.0466 (8)0.0029 (6)0.0177 (6)0.0024 (6)
C130.0311 (7)0.0470 (8)0.0442 (8)−0.0004 (6)0.0203 (6)0.0012 (6)
C140.0413 (8)0.0624 (10)0.0590 (10)0.0025 (7)0.0262 (7)0.0196 (8)
C150.0429 (9)0.1156 (16)0.0581 (10)0.0101 (10)0.0279 (8)0.0288 (11)
C160.0689 (14)0.195 (3)0.0909 (17)0.0497 (17)0.0475 (13)0.078 (2)
C170.125 (2)0.0777 (15)0.129 (2)−0.0289 (14)0.083 (2)0.0060 (14)
C180.0423 (9)0.1250 (18)0.0686 (12)0.0133 (10)0.0340 (9)0.0399 (12)
C190.0299 (7)0.0508 (8)0.0478 (8)0.0040 (6)0.0176 (6)0.0065 (6)
C200.0319 (7)0.0571 (9)0.0484 (8)0.0031 (6)0.0191 (6)0.0033 (7)
C210.0432 (8)0.0526 (9)0.0642 (10)0.0049 (7)0.0251 (8)0.0062 (8)
C220.0806 (14)0.0597 (11)0.0947 (15)0.0130 (10)0.0385 (12)−0.0020 (11)
C230.0811 (14)0.0732 (13)0.0703 (12)0.0236 (11)0.0330 (11)0.0244 (10)
C240.280 (6)0.137 (3)0.115 (3)0.066 (4)0.070 (4)−0.008 (3)
Geometric parameters (Å, °) top
O1—C31.3547 (18)C12—C191.5183 (19)
O1—H1O10.85 (3)C14—C151.506 (3)
O2—C41.3529 (19)C14—C171.531 (3)
O2—H1O20.8200C14—C181.543 (2)
O3—C71.2617 (18)C15—C161.324 (3)
O4—C131.3526 (17)C15—H15A0.9300
O4—H1O40.8200C16—H16A0.9300
O5—C111.3550 (18)C16—H16B0.9300
O5—H5A0.89 (3)C17—H17A0.9600
O6—C91.3616 (17)C17—H17B0.9600
O6—C51.3627 (17)C17—H17C0.9600
O7—C241.279 (5)C18—H18A0.9600
O7—H1O70.831 (10)C18—H18B0.9600
C1—C21.370 (2)C18—H18C0.9600
C1—C61.405 (2)C19—C201.499 (2)
C1—H1B0.9300C19—H19A0.9700
C2—C31.393 (2)C19—H19B0.9700
C2—H2A0.9300C20—C211.324 (2)
C3—C41.385 (2)C20—H20A0.9300
C4—C51.391 (2)C21—C231.496 (3)
C5—C61.389 (2)C21—C221.507 (3)
C6—C71.445 (2)C22—H22A0.9600
C7—C81.443 (2)C22—H22B0.9600
C8—C91.410 (2)C22—H22C0.9600
C8—C131.4193 (19)C23—H23A0.9600
C9—C101.392 (2)C23—H23B0.9600
C10—C111.411 (2)C23—H23C0.9600
C10—C141.551 (2)C24—H24A0.9600
C11—C121.404 (2)C24—H24B0.9600
C12—C131.376 (2)C24—H24C0.9600
C3—O1—H1O1109.7 (18)C18—C14—C10116.03 (13)
C4—O2—H1O2109.5C16—C15—C14127.2 (3)
C13—O4—H1O4109.5C16—C15—H15A116.4
C11—O5—H5A108.6 (17)C14—C15—H15A116.4
C9—O6—C5121.30 (11)C15—C16—H16A120.0
C24—O7—H1O7104 (3)C15—C16—H16B120.0
C2—C1—C6120.51 (14)H16A—C16—H16B120.0
C2—C1—H1B119.7C14—C17—H17A109.5
C6—C1—H1B119.7C14—C17—H17B109.5
C1—C2—C3120.42 (14)H17A—C17—H17B109.5
C1—C2—H2A119.8C14—C17—H17C109.5
C3—C2—H2A119.8H17A—C17—H17C109.5
O1—C3—C4115.40 (14)H17B—C17—H17C109.5
O1—C3—C2124.11 (14)C14—C18—H18A109.5
C4—C3—C2120.49 (14)C14—C18—H18B109.5
O2—C4—C3123.39 (13)H18A—C18—H18B109.5
O2—C4—C5118.20 (13)C14—C18—H18C109.5
C3—C4—C5118.39 (14)H18A—C18—H18C109.5
O6—C5—C6122.75 (12)H18B—C18—H18C109.5
O6—C5—C4115.11 (12)C20—C19—C12112.88 (12)
C6—C5—C4122.13 (13)C20—C19—H19A109.0
C5—C6—C1118.02 (13)C12—C19—H19A109.0
C5—C6—C7118.51 (13)C20—C19—H19B109.0
C1—C6—C7123.47 (13)C12—C19—H19B109.0
O3—C7—C8121.37 (13)H19A—C19—H19B107.8
O3—C7—C6121.45 (13)C21—C20—C19128.13 (15)
C8—C7—C6117.18 (12)C21—C20—H20A115.9
C9—C8—C13117.94 (13)C19—C20—H20A115.9
C9—C8—C7120.60 (13)C20—C21—C23124.55 (17)
C13—C8—C7121.46 (13)C20—C21—C22121.00 (17)
O6—C9—C10116.49 (12)C23—C21—C22114.45 (16)
O6—C9—C8119.66 (12)C21—C22—H22A109.5
C10—C9—C8123.84 (13)C21—C22—H22B109.5
C9—C10—C11114.48 (13)H22A—C22—H22B109.5
C9—C10—C14125.11 (13)C21—C22—H22C109.5
C11—C10—C14120.26 (13)H22A—C22—H22C109.5
O5—C11—C12113.44 (13)H22B—C22—H22C109.5
O5—C11—C10121.74 (13)C21—C23—H23A109.5
C12—C11—C10124.81 (13)C21—C23—H23B109.5
C13—C12—C11117.79 (12)H23A—C23—H23B109.5
C13—C12—C19121.96 (13)C21—C23—H23C109.5
C11—C12—C19120.25 (13)H23A—C23—H23C109.5
O4—C13—C12119.35 (12)H23B—C23—H23C109.5
O4—C13—C8119.54 (13)O7—C24—H24A109.5
C12—C13—C8121.11 (13)O7—C24—H24B109.5
C15—C14—C17112.63 (19)H24A—C24—H24B109.5
C15—C14—C18102.58 (16)O7—C24—H24C109.5
C17—C14—C18108.52 (18)H24A—C24—H24C109.5
C15—C14—C10110.00 (14)H24B—C24—H24C109.5
C17—C14—C10107.19 (16)
C6—C1—C2—C3−0.3 (2)C8—C9—C10—C11−0.6 (2)
C1—C2—C3—O1−178.16 (15)O6—C9—C10—C142.9 (2)
C1—C2—C3—C42.0 (2)C8—C9—C10—C14−176.02 (14)
O1—C3—C4—O2−0.4 (2)C9—C10—C11—O5−176.97 (14)
C2—C3—C4—O2179.48 (15)C14—C10—C11—O5−1.3 (2)
O1—C3—C4—C5177.91 (14)C9—C10—C11—C121.9 (2)
C2—C3—C4—C5−2.2 (2)C14—C10—C11—C12177.57 (15)
C9—O6—C5—C6−0.3 (2)O5—C11—C12—C13176.72 (14)
C9—O6—C5—C4178.79 (13)C10—C11—C12—C13−2.2 (2)
O2—C4—C5—O60.1 (2)O5—C11—C12—C19−2.8 (2)
C3—C4—C5—O6−178.31 (13)C10—C11—C12—C19178.28 (14)
O2—C4—C5—C6179.21 (14)C11—C12—C13—O4−179.14 (13)
C3—C4—C5—C60.8 (2)C19—C12—C13—O40.4 (2)
O6—C5—C6—C1179.88 (13)C11—C12—C13—C81.2 (2)
C4—C5—C6—C10.8 (2)C19—C12—C13—C8−179.33 (13)
O6—C5—C6—C70.5 (2)C9—C8—C13—O4−179.69 (13)
C4—C5—C6—C7−178.59 (13)C7—C8—C13—O41.2 (2)
C2—C1—C6—C5−1.1 (2)C9—C8—C13—C120.0 (2)
C2—C1—C6—C7178.30 (14)C7—C8—C13—C12−179.13 (14)
C5—C6—C7—O3179.25 (14)C9—C10—C14—C15−137.06 (17)
C1—C6—C7—O3−0.1 (2)C11—C10—C14—C1547.7 (2)
C5—C6—C7—C8−0.4 (2)C9—C10—C14—C17100.2 (2)
C1—C6—C7—C8−179.77 (14)C11—C10—C14—C17−75.0 (2)
O3—C7—C8—C9−179.44 (14)C9—C10—C14—C18−21.2 (3)
C6—C7—C8—C90.2 (2)C11—C10—C14—C18163.56 (17)
O3—C7—C8—C13−0.3 (2)C17—C14—C15—C16−12.2 (3)
C6—C7—C8—C13179.32 (13)C18—C14—C15—C16104.3 (2)
C5—O6—C9—C10−178.87 (13)C10—C14—C15—C16−131.7 (2)
C5—O6—C9—C80.1 (2)C13—C12—C19—C20−93.25 (17)
C13—C8—C9—O6−179.22 (12)C11—C12—C19—C2086.25 (17)
C7—C8—C9—O6−0.1 (2)C12—C19—C20—C21−115.91 (17)
C13—C8—C9—C10−0.3 (2)C19—C20—C21—C23−0.3 (3)
C7—C8—C9—C10178.84 (14)C19—C20—C21—C22−179.77 (16)
O6—C9—C10—C11178.37 (13)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1O1···O7i0.85 (3)1.79 (3)2.632 (2)170 (3)
O2—H1O2···O10.822.292.7117 (19)113
O2—H1O2···O4ii0.822.032.7995 (19)155
O4—H1O4···O30.821.812.5505 (18)149
O7—H1O7···O3i0.83 (2)1.954 (19)2.755 (2)161 (4)
C18—H18B···O60.962.252.638 (2)103
C19—H19A···O2iii0.972.543.378 (2)145
C19—H19A···O40.972.502.8451 (19)101
C22—H22B···Cg1iv0.963.103.705 (2)123
Symmetry codes: (i) x−1, y, z−1; (ii) x−1, y, z; i; (iii) x+1, y, z; (iv) x+1, −y−1/2, z−1/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1O1···O7i0.85 (3)1.79 (3)2.632 (2)170 (3)
O2—H1O2···O10.822.292.7117 (19)113
O2—H1O2···O4ii0.822.032.7995 (19)155
O4—H1O4···O30.821.812.5505 (18)149
O7—H1O7···O3i0.83 (2)1.954 (19)2.755 (2)161 (4)
C18—H18B···O60.962.252.638 (2)103
C19—H19A···O2iii0.972.543.378 (2)145
C19—H19A···O40.972.502.8451 (19)101
C22—H22B···Cg1iv0.963.103.705 (2)123
Symmetry codes: (i) x−1, y, z−1; (ii) x−1, y, z; i; (iii) x+1, y, z; (iv) x+1, −y−1/2, z−1/2.
Acknowledgements top

This work was supported by the programme Directed Basic Research in Medicinal Chemistry (Thailand Research Fund) (grant No. DBG4880019). The authors also thank Prince of Songkla University, the Malaysian Government and Universiti Sains Malaysia for a Scientific Advancement Grant Allocation (SAGA) (grant No. 304/PFIZIK/653003/A118).

references
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