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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2844.
Published online 2010 October 20. doi:  10.1107/S1600536810040559
PMCID: PMC3009189

Curcumenol from Curcuma zedoaria: a second monoclinic modification

Abstract

The title compound, systematic name 9-isopropyl­idene-2,6-dimethyl-11-oxatricyclo­[6.2.1.01,5]undec-6-en-8-ol, C15H22O2, which crystallizes with two mol­ecules of similar conformation in the asymmetric unit, features three fused rings, two of which are five-membered and the third six-membered. Of the two five-membered rings, the one with an O atom has a distinct envelope shape (with the O atom representing the flap). The six-membered ring is also envelope-shaped as it shares a common O atom with the five-membered ring. In the crystal, the two independent mol­ecules are linked by a pair of O—H(...)O hydrogen bonds, generating a dimer.

Related literature

For the C2 modification isolated from Globba malaccensis Ridl, see: Muangsin et al. (2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2844-scheme1.jpg

Experimental

Crystal data

  • C15H22O2
  • M r = 234.33
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2844-efi1.jpg
  • a = 9.3495 (7) Å
  • b = 12.535 (1) Å
  • c = 11.7727 (9) Å
  • β = 96.532 (1)°
  • V = 1370.76 (18) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 100 K
  • 0.40 × 0.05 × 0.05 mm

Data collection

  • Bruker SMART APEX diffractometer
  • 13257 measured reflections
  • 3298 independent reflections
  • 2882 reflections with I > 2σ(I)
  • R int = 0.046

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.090
  • S = 1.03
  • 3298 reflections
  • 323 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810040559/hb5676sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040559/hb5676Isup2.hkl

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

Acknowledgments

We thank the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

Zingerberaceae is a herbaceous plant found in tropical forests that comprises of 52 genera with 1500 species. Most species are found in the South East Asian region. Curcuma zedoaria, also known as white turmeric, is a species that is a rich source of terpenoids.

Curcumenol, isolated from Globba malaccensis Ridl, belongs to the monoclinic, space group C2, with a 16.8467 (4), b 7.6799 (2), c 11.8613 (10) Å and β 115.997 (1) °. This modification is less dense, as noted from its calculated density of 1.28 (Muangsin et al., 2004). The present modification (I), (Fig. 1) shows nearly identical bond dimensions in the two independent molecules. The two molecules form a dimer in the crystal, being linked by two O—H···O hydrogen bonds.

Experimental

The rhizome of Curcuma zedoaria was collected from Tawangmangu, Indonesia.

Dried rhizomes (1 kg) were powdered and extracted three times with n-hexane and after this, with dichloromethane, ethylacetate, and methanol. The extracts were concentrated under reduced pressure given several fractions.

The n-hexane crude extract (20 g) was subjected to column chromatography over silica gel 60(0.063–0.200 mm, 70–230 mesh ASTM) eluted with a mixture of n-hexane: ethyl acetate with increasing polarity. Separation by TLC gave 21 fractions.

Fraction 10 (1.41 g) was chromatographed over silica gel (0.040–0.063 mm, mesh 230–400 ASTM) eluted with a gradient solvent system of n-hexane: ethyl aceate to give 5 fractions. The second fraction was further purified by high performance thin layerchromatography and using petroleum ether: ethyl acetate: acidified methanol in a 85:14:1 ratio as the developing solvent. Slow evaporation of the solvent gave (I) as colorless prisms.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C).

In the absence of heavy atoms, 2923 Friedel pairs were merged.

The hydroxy H-atoms were located in a difference Fourier map, and were refined without restraints; their Uiso values were freely refined.

The absolute configuration was assumed to be that of the C2 modification.

Figures

Fig. 1.
View of the first molecule of (I) at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
Fig. 2.
View of the second molecule of (I) at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C15H22O2F(000) = 512
Mr = 234.33Dx = 1.135 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 3511 reflections
a = 9.3495 (7) Åθ = 2.4–27.4°
b = 12.535 (1) ŵ = 0.07 mm1
c = 11.7727 (9) ÅT = 100 K
β = 96.532 (1)°Prism, colorless
V = 1370.76 (18) Å30.40 × 0.05 × 0.05 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer2882 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.046
graphiteθmax = 27.5°, θmin = 2.2°
ω scansh = −12→12
13257 measured reflectionsk = −16→15
3298 independent reflectionsl = −15→15

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H atoms treated by a mixture of independent and constrained refinement
S = 1.03w = 1/[σ2(Fo2) + (0.0535P)2 + 0.0302P] where P = (Fo2 + 2Fc2)/3
3298 reflections(Δ/σ)max = 0.001
323 parametersΔρmax = 0.21 e Å3
1 restraintΔρmin = −0.18 e Å3

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

xyzUiso*/Ueq
O10.24626 (15)0.50024 (12)0.49296 (13)0.0165 (3)
H10.268 (3)0.497 (2)0.569 (3)0.033 (7)*
O20.06839 (14)0.62132 (11)0.52267 (11)0.0136 (3)
O30.03989 (15)0.49267 (12)0.71017 (12)0.0160 (3)
H30.045 (3)0.538 (3)0.656 (3)0.043 (9)*
O40.28533 (14)0.46600 (12)0.72943 (11)0.0137 (3)
C10.2006 (2)0.60463 (17)0.47181 (17)0.0141 (4)
C20.1560 (2)0.62872 (17)0.34601 (17)0.0153 (4)
C30.2186 (2)0.59756 (17)0.25570 (17)0.0178 (4)
C40.1634 (3)0.6348 (2)0.13744 (18)0.0266 (5)
H4A0.06710.66560.13810.040*
H4B0.15840.57410.08460.040*
H4C0.22870.68900.11250.040*
C50.3508 (2)0.52777 (19)0.2618 (2)0.0231 (5)
H5A0.38780.51570.34210.035*
H5B0.42480.56310.22260.035*
H5C0.32570.45920.22480.035*
C60.0287 (2)0.70366 (17)0.34497 (17)0.0171 (4)
H6A−0.05950.67100.30510.020*
H6B0.04760.77190.30700.020*
C70.0140 (2)0.72101 (17)0.47172 (17)0.0144 (4)
C8−0.1354 (2)0.74213 (18)0.50599 (18)0.0188 (4)
H8−0.17860.80260.45840.023*
C9−0.2388 (2)0.6479 (2)0.4898 (2)0.0252 (5)
H9A−0.25240.62760.40890.038*
H9B−0.33170.66810.51450.038*
H9C−0.19870.58740.53560.038*
C10−0.1057 (2)0.7814 (2)0.62979 (19)0.0231 (5)
H10A−0.09600.72040.68340.028*
H10B−0.18510.82770.64950.028*
C110.0359 (2)0.84454 (19)0.63593 (19)0.0232 (5)
H11A0.10000.82540.70570.028*
H11B0.01680.92220.63710.028*
C120.1062 (2)0.81353 (17)0.52712 (17)0.0169 (4)
H120.09640.87560.47340.020*
C130.2640 (2)0.78423 (17)0.54836 (17)0.0165 (4)
C140.3074 (2)0.68708 (17)0.52234 (17)0.0153 (4)
H140.40670.66930.53570.018*
C150.3668 (2)0.86938 (19)0.5957 (2)0.0242 (5)
H15A0.46470.84020.60690.036*
H15B0.33950.89420.66920.036*
H15C0.36340.92930.54200.036*
C160.1638 (2)0.50276 (17)0.78584 (16)0.0139 (4)
C170.1685 (2)0.42847 (17)0.88859 (17)0.0151 (4)
C180.0631 (2)0.40510 (18)0.95131 (17)0.0185 (4)
C190.0876 (2)0.3318 (2)1.0536 (2)0.0269 (5)
H19A0.18590.30351.05960.040*
H19B0.01870.27261.04430.040*
H19C0.07400.37171.12320.040*
C20−0.0861 (2)0.4506 (2)0.9308 (2)0.0283 (6)
H20A−0.09080.50240.86810.042*
H20B−0.10990.48611.00040.042*
H20C−0.15520.39300.91050.042*
C210.3243 (2)0.39168 (18)0.91067 (17)0.0173 (4)
H21A0.33220.31380.89860.021*
H21B0.36590.40920.98950.021*
C220.3990 (2)0.45412 (18)0.82278 (17)0.0154 (4)
C230.5286 (2)0.40276 (19)0.77721 (18)0.0199 (5)
H230.59900.38320.84440.024*
C240.4981 (3)0.3034 (2)0.7059 (2)0.0280 (5)
H24A0.45030.25040.74990.042*
H24B0.58880.27380.68550.042*
H24C0.43540.32130.63610.042*
C250.5938 (2)0.4943 (2)0.71440 (19)0.0229 (5)
H25A0.54500.50110.63560.027*
H25B0.69770.48180.71050.027*
C260.5709 (2)0.5955 (2)0.7840 (2)0.0247 (5)
H26A0.53880.65550.73270.030*
H26B0.66130.61620.83100.030*
C270.4527 (2)0.56609 (18)0.86173 (17)0.0172 (4)
H270.49960.56040.94220.021*
C280.3310 (2)0.64559 (18)0.85997 (17)0.0176 (4)
C290.1969 (2)0.61599 (17)0.82481 (17)0.0160 (4)
H290.12100.66640.82410.019*
C300.3704 (3)0.75649 (19)0.9014 (2)0.0253 (5)
H30A0.28330.80040.89770.038*
H30B0.43780.78800.85290.038*
H30C0.41580.75320.98060.038*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0223 (7)0.0128 (7)0.0142 (8)0.0047 (6)0.0011 (6)0.0017 (6)
O20.0151 (6)0.0123 (7)0.0137 (7)0.0011 (5)0.0026 (5)0.0029 (6)
O30.0140 (7)0.0201 (8)0.0134 (7)−0.0019 (6)−0.0002 (5)0.0034 (6)
O40.0115 (6)0.0172 (8)0.0123 (7)0.0015 (6)0.0014 (5)0.0005 (6)
C10.0155 (9)0.0134 (10)0.0136 (9)0.0016 (8)0.0027 (7)0.0000 (8)
C20.0168 (9)0.0130 (10)0.0158 (10)−0.0015 (8)0.0002 (7)0.0001 (8)
C30.0241 (10)0.0146 (10)0.0150 (10)−0.0019 (9)0.0029 (8)0.0000 (8)
C40.0398 (13)0.0256 (12)0.0142 (10)0.0004 (11)0.0028 (9)−0.0020 (9)
C50.0294 (12)0.0206 (12)0.0209 (11)0.0032 (9)0.0097 (9)0.0001 (9)
C60.0192 (10)0.0173 (11)0.0144 (10)−0.0004 (8)0.0003 (8)0.0017 (8)
C70.0150 (9)0.0121 (10)0.0157 (10)0.0020 (8)0.0006 (7)0.0032 (8)
C80.0176 (10)0.0192 (12)0.0200 (10)0.0042 (8)0.0045 (8)0.0044 (9)
C90.0153 (10)0.0272 (13)0.0333 (13)0.0004 (9)0.0043 (9)0.0051 (10)
C100.0243 (11)0.0230 (12)0.0231 (11)0.0077 (9)0.0080 (9)0.0025 (9)
C110.0266 (11)0.0226 (13)0.0201 (11)0.0070 (10)0.0012 (9)−0.0038 (9)
C120.0229 (10)0.0127 (10)0.0147 (10)0.0015 (8)0.0012 (8)0.0020 (8)
C130.0203 (10)0.0153 (11)0.0138 (10)−0.0030 (8)0.0011 (8)0.0028 (8)
C140.0139 (9)0.0190 (11)0.0128 (10)−0.0013 (8)0.0011 (7)0.0036 (8)
C150.0260 (11)0.0192 (12)0.0263 (12)−0.0064 (9)−0.0014 (9)0.0006 (10)
C160.0130 (9)0.0163 (10)0.0122 (9)0.0007 (8)0.0016 (7)0.0002 (8)
C170.0159 (9)0.0152 (10)0.0134 (9)−0.0011 (8)−0.0015 (8)0.0002 (8)
C180.0192 (10)0.0214 (12)0.0144 (10)−0.0023 (9)−0.0003 (8)0.0024 (9)
C190.0257 (12)0.0342 (14)0.0205 (11)−0.0088 (10)0.0016 (9)0.0083 (10)
C200.0165 (11)0.0448 (16)0.0241 (12)−0.0011 (11)0.0049 (9)0.0047 (11)
C210.0172 (10)0.0199 (11)0.0144 (10)0.0026 (9)0.0010 (8)0.0033 (8)
C220.0123 (9)0.0213 (11)0.0119 (10)0.0018 (8)−0.0023 (7)0.0017 (8)
C230.0155 (10)0.0271 (13)0.0173 (10)0.0053 (9)0.0021 (8)0.0033 (9)
C240.0269 (11)0.0262 (14)0.0322 (13)0.0075 (10)0.0096 (10)−0.0035 (10)
C250.0163 (10)0.0322 (13)0.0206 (11)0.0011 (9)0.0040 (8)0.0044 (10)
C260.0169 (10)0.0300 (13)0.0272 (12)−0.0034 (9)0.0034 (9)0.0039 (10)
C270.0158 (10)0.0238 (12)0.0114 (10)−0.0031 (8)−0.0008 (8)−0.0002 (8)
C280.0228 (10)0.0179 (11)0.0128 (10)−0.0004 (9)0.0041 (8)−0.0005 (8)
C290.0183 (9)0.0151 (11)0.0150 (10)0.0018 (8)0.0044 (8)0.0014 (8)
C300.0295 (12)0.0221 (12)0.0240 (12)−0.0065 (10)0.0023 (9)−0.0060 (10)

Geometric parameters (Å, °)

O1—C11.390 (3)C14—H140.9500
O1—H10.89 (3)C15—H15A0.9800
O2—C11.449 (2)C15—H15B0.9800
O2—C71.453 (2)C15—H15C0.9800
O3—C161.385 (2)C16—C291.513 (3)
O3—H30.86 (3)C16—C171.523 (3)
O4—C221.447 (2)C17—C181.329 (3)
O4—C161.455 (2)C17—C211.522 (3)
C1—C141.511 (3)C18—C201.501 (3)
C1—C21.523 (3)C18—C191.512 (3)
C2—C31.329 (3)C19—H19A0.9800
C2—C61.515 (3)C19—H19B0.9800
C3—C41.503 (3)C19—H19C0.9800
C3—C51.510 (3)C20—H20A0.9800
C4—H4A0.9800C20—H20B0.9800
C4—H4B0.9800C20—H20C0.9800
C4—H4C0.9800C21—C221.529 (3)
C5—H5A0.9800C21—H21A0.9900
C5—H5B0.9800C21—H21B0.9900
C5—H5C0.9800C22—C231.522 (3)
C6—C71.530 (3)C22—C271.542 (3)
C6—H6A0.9900C23—C241.511 (3)
C6—H6B0.9900C23—C251.529 (3)
C7—C81.521 (3)C23—H231.0000
C7—C121.545 (3)C24—H24A0.9800
C8—C91.524 (3)C24—H24B0.9800
C8—C101.534 (3)C24—H24C0.9800
C8—H81.0000C25—C261.539 (3)
C9—H9A0.9800C25—H25A0.9900
C9—H9B0.9800C25—H25B0.9900
C9—H9C0.9800C26—C271.557 (3)
C10—C111.537 (3)C26—H26A0.9900
C10—H10A0.9900C26—H26B0.9900
C10—H10B0.9900C27—C281.511 (3)
C11—C121.554 (3)C27—H271.0000
C11—H11A0.9900C28—C291.328 (3)
C11—H11B0.9900C28—C301.505 (3)
C12—C131.514 (3)C29—H290.9500
C12—H121.0000C30—H30A0.9800
C13—C141.330 (3)C30—H30B0.9800
C13—C151.500 (3)C30—H30C0.9800
C1—O1—H1105 (2)H15A—C15—H15C109.5
C1—O2—C7103.23 (13)H15B—C15—H15C109.5
C16—O3—H3108 (2)O3—C16—O4108.49 (15)
C22—O4—C16103.31 (13)O3—C16—C29114.09 (17)
O1—C1—O2108.73 (15)O4—C16—C29106.99 (15)
O1—C1—C14113.42 (17)O3—C16—C17113.64 (17)
O2—C1—C14107.18 (16)O4—C16—C17102.46 (15)
O1—C1—C2113.92 (17)C29—C16—C17110.27 (16)
O2—C1—C2102.77 (15)C18—C17—C21126.42 (19)
C14—C1—C2110.05 (16)C18—C17—C16128.31 (19)
C3—C2—C6126.34 (18)C21—C17—C16105.13 (16)
C3—C2—C1128.53 (19)C17—C18—C20124.1 (2)
C6—C2—C1105.00 (16)C17—C18—C19121.5 (2)
C2—C3—C4120.92 (19)C20—C18—C19114.39 (18)
C2—C3—C5124.38 (19)C18—C19—H19A109.5
C4—C3—C5114.66 (17)C18—C19—H19B109.5
C3—C4—H4A109.5H19A—C19—H19B109.5
C3—C4—H4B109.5C18—C19—H19C109.5
H4A—C4—H4B109.5H19A—C19—H19C109.5
C3—C4—H4C109.5H19B—C19—H19C109.5
H4A—C4—H4C109.5C18—C20—H20A109.5
H4B—C4—H4C109.5C18—C20—H20B109.5
C3—C5—H5A109.5H20A—C20—H20B109.5
C3—C5—H5B109.5C18—C20—H20C109.5
H5A—C5—H5B109.5H20A—C20—H20C109.5
C3—C5—H5C109.5H20B—C20—H20C109.5
H5A—C5—H5C109.5C17—C21—C22103.41 (16)
H5B—C5—H5C109.5C17—C21—H21A111.1
C2—C6—C7103.77 (16)C22—C21—H21A111.1
C2—C6—H6A111.0C17—C21—H21B111.1
C7—C6—H6A111.0C22—C21—H21B111.1
C2—C6—H6B111.0H21A—C21—H21B109.0
C7—C6—H6B111.0O4—C22—C23108.73 (16)
H6A—C6—H6B109.0O4—C22—C21102.34 (15)
O2—C7—C8109.23 (15)C23—C22—C21117.75 (18)
O2—C7—C6102.38 (16)O4—C22—C27108.54 (16)
C8—C7—C6118.09 (17)C23—C22—C27104.17 (16)
O2—C7—C12108.61 (15)C21—C22—C27115.02 (16)
C8—C7—C12104.05 (16)C24—C23—C22115.91 (18)
C6—C7—C12114.25 (16)C24—C23—C25114.24 (18)
C7—C8—C9114.86 (18)C22—C23—C25103.31 (18)
C7—C8—C10103.63 (17)C24—C23—H23107.7
C9—C8—C10114.29 (18)C22—C23—H23107.7
C7—C8—H8107.9C25—C23—H23107.7
C9—C8—H8107.9C23—C24—H24A109.5
C10—C8—H8107.9C23—C24—H24B109.5
C8—C9—H9A109.5H24A—C24—H24B109.5
C8—C9—H9B109.5C23—C24—H24C109.5
H9A—C9—H9B109.5H24A—C24—H24C109.5
C8—C9—H9C109.5H24B—C24—H24C109.5
H9A—C9—H9C109.5C23—C25—C26105.89 (17)
H9B—C9—H9C109.5C23—C25—H25A110.6
C8—C10—C11105.77 (17)C26—C25—H25A110.6
C8—C10—H10A110.6C23—C25—H25B110.6
C11—C10—H10A110.6C26—C25—H25B110.6
C8—C10—H10B110.6H25A—C25—H25B108.7
C11—C10—H10B110.6C25—C26—C27105.59 (19)
H10A—C10—H10B108.7C25—C26—H26A110.6
C10—C11—C12105.99 (18)C27—C26—H26A110.6
C10—C11—H11A110.5C25—C26—H26B110.6
C12—C11—H11A110.5C27—C26—H26B110.6
C10—C11—H11B110.5H26A—C26—H26B108.8
C12—C11—H11B110.5C28—C27—C22112.18 (17)
H11A—C11—H11B108.7C28—C27—C26114.80 (18)
C13—C12—C7111.99 (17)C22—C27—C26105.62 (17)
C13—C12—C11114.85 (17)C28—C27—H27108.0
C7—C12—C11105.52 (17)C22—C27—H27108.0
C13—C12—H12108.1C26—C27—H27108.0
C7—C12—H12108.1C29—C28—C30123.2 (2)
C11—C12—H12108.1C29—C28—C27120.2 (2)
C14—C13—C15122.5 (2)C30—C28—C27116.66 (18)
C14—C13—C12120.07 (19)C28—C29—C16120.68 (18)
C15—C13—C12117.38 (19)C28—C29—H29119.7
C13—C14—C1120.76 (19)C16—C29—H29119.7
C13—C14—H14119.6C28—C30—H30A109.5
C1—C14—H14119.6C28—C30—H30B109.5
C13—C15—H15A109.5H30A—C30—H30B109.5
C13—C15—H15B109.5C28—C30—H30C109.5
H15A—C15—H15B109.5H30A—C30—H30C109.5
C13—C15—H15C109.5H30B—C30—H30C109.5
C7—O2—C1—O1−166.41 (15)C22—O4—C16—O3−165.83 (16)
C7—O2—C1—C1470.62 (18)C22—O4—C16—C2970.65 (18)
C7—O2—C1—C2−45.36 (18)C22—O4—C16—C17−45.36 (18)
O1—C1—C2—C3−41.0 (3)O3—C16—C17—C18−42.5 (3)
O2—C1—C2—C3−158.4 (2)O4—C16—C17—C18−159.3 (2)
C14—C1—C2—C387.7 (3)C29—C16—C17—C1887.1 (3)
O1—C1—C2—C6142.99 (17)O3—C16—C17—C21141.52 (17)
O2—C1—C2—C625.6 (2)O4—C16—C17—C2124.7 (2)
C14—C1—C2—C6−88.34 (19)C29—C16—C17—C21−88.93 (19)
C6—C2—C3—C4−1.1 (3)C21—C17—C18—C20175.0 (2)
C1—C2—C3—C4−176.4 (2)C16—C17—C18—C20−0.2 (4)
C6—C2—C3—C5176.2 (2)C21—C17—C18—C19−2.8 (4)
C1—C2—C3—C51.0 (4)C16—C17—C18—C19−178.0 (2)
C3—C2—C6—C7−173.7 (2)C18—C17—C21—C22−172.6 (2)
C1—C2—C6—C72.5 (2)C16—C17—C21—C223.6 (2)
C1—O2—C7—C8172.96 (16)C16—O4—C22—C23173.18 (17)
C1—O2—C7—C647.00 (17)C16—O4—C22—C2147.91 (18)
C1—O2—C7—C12−74.17 (17)C16—O4—C22—C27−74.09 (17)
C2—C6—C7—O2−29.52 (19)C17—C21—C22—O4−30.8 (2)
C2—C6—C7—C8−149.48 (18)C17—C21—C22—C23−149.86 (18)
C2—C6—C7—C1287.7 (2)C17—C21—C22—C2786.7 (2)
O2—C7—C8—C9−48.6 (2)O4—C22—C23—C24−49.5 (2)
C6—C7—C8—C967.7 (2)C21—C22—C23—C2466.2 (3)
C12—C7—C8—C9−164.47 (18)C27—C22—C23—C24−165.10 (18)
O2—C7—C8—C1076.7 (2)O4—C22—C23—C2576.2 (2)
C6—C7—C8—C10−166.94 (19)C21—C22—C23—C25−168.10 (18)
C12—C7—C8—C10−39.1 (2)C27—C22—C23—C25−39.4 (2)
C7—C8—C10—C1134.1 (2)C24—C23—C25—C26162.08 (18)
C9—C8—C10—C11159.84 (18)C22—C23—C25—C2635.3 (2)
C8—C10—C11—C12−15.7 (2)C23—C25—C26—C27−17.4 (2)
O2—C7—C12—C1338.7 (2)O4—C22—C27—C2838.7 (2)
C8—C7—C12—C13155.00 (16)C23—C22—C27—C28154.41 (17)
C6—C7—C12—C13−74.8 (2)C21—C22—C27—C28−75.2 (2)
O2—C7—C12—C11−86.90 (18)O4—C22—C27—C26−87.07 (18)
C8—C7—C12—C1129.4 (2)C23—C22—C27—C2628.7 (2)
C6—C7—C12—C11159.54 (17)C21—C22—C27—C26159.03 (17)
C10—C11—C12—C13−132.17 (19)C25—C26—C27—C28−131.0 (2)
C10—C11—C12—C7−8.3 (2)C25—C26—C27—C22−6.9 (2)
C7—C12—C13—C14−1.7 (3)C22—C27—C28—C29−1.6 (3)
C11—C12—C13—C14118.7 (2)C26—C27—C28—C29119.0 (2)
C7—C12—C13—C15176.55 (17)C22—C27—C28—C30177.41 (17)
C11—C12—C13—C15−63.1 (2)C26—C27—C28—C30−62.0 (2)
C15—C13—C14—C1−178.33 (18)C30—C28—C29—C16−179.05 (19)
C12—C13—C14—C1−0.2 (3)C27—C28—C29—C16−0.1 (3)
O1—C1—C14—C13−154.67 (18)O3—C16—C29—C28−154.60 (18)
O2—C1—C14—C13−34.7 (2)O4—C16—C29—C28−34.6 (2)
C2—C1—C14—C1376.4 (2)C17—C16—C29—C2876.1 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O40.89 (3)1.92 (3)2.799 (2)168 (3)
O3—H3···O20.86 (3)1.92 (3)2.771 (2)171 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5676).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Muangsin, N., Ngamrojnavanich, N., Onanong, S., Chaichit, N., Roengsumran, S. & Petsom, A. (2004). J. Struct. Chem.45, 293–297.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.

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