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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 7| July 2015| Pages o483-o484
doi:10.1107/S2056989015011214

Crystal structure of 15,16-ep­­oxy-7β,9α-di­hy­droxy­labdane-13(16),14-dien-6-one

CROSSMARK_Color_square_no_text.svg
Vikram Dev Singh,a Kamni,a Musarat Amina,b Nawal Al-Musayeib,b Sumati Anthalc and Rajni Kantc*

aFaculty of Sciences, Shri Mata Vaishno Devi University, Katra 182 320, Jammu, J & K, India, bDepartment of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, and cPost-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India
*Correspondence e-mail: rkant.ju@gmail.com

Edited by A. J. Lough, University of Toronto, Canada (Received 21 May 2015; accepted 9 June 2015; online 13 June 2015)

In the title mol­ecule, C20H30O4, both cyclo­hexane rings adopt chair conformations. In the crystal, mol­ecules are connected by O—H⋯O hydrogen bonds forming chains along [100]. In addtion, an intra­molecular O—H⋯O hydrogen bond forms an S(5) ring.

CCDC reference: 1405794

1. Related literature

For background to the title compound, see: Al-Musayeib et al. (2000[Al-Musayeib, N. M., Abbas, F. A., Ahmad, M. S., Mossa, J. S. & El-Feraly, F. S. (2000). Phytochemistry, 54, 771-775.]); Shaw (1985[Shaw, A. (1985). BOOK TITLE?, p. 835. Cambridge University Press.]). For its biological activities, see: Mossa et al. (2000[Mossa, J. S., Al-Yahya, M. A. & Al-Meshal, I. A. (2000). In Medicinal Plants of Saudi Arabia. Riyadh: King Saud University Press.]); Kidane et al. (2013[Kidane, D., Tomass, Z. & Dejene, T. (2013). Sci. Res. Essays, 8, 1139-1144.]). For the synthesis and spectroscopic data, see: Savona et al. (1976[Savona, G., Piozzi, F., Hanson, J. R. & Siverns, M. (1976). J. Chem. Soc. Perkin Trans. 1, pp. 1607-1609.],1977[Savona, G., Piozzi, F., Hanson, J. R. & Siverns, M. (1977). J. Chem. Soc. Perkin Trans. 1, pp. 322-324.]); Hon et al. (1993[Hon, P. M., Wang, E. S., Lam, S. K. M., Choy, Y. M., Lee, C. M. & Wong, H. N. C. (1993). Phytochemistry, 33, 639-641.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C20H30O4

  • Mr = 334.44

  • Orthorhombic, P 21 21 21

  • a = 8.5757 (7) Å

  • b = 9.2957 (8) Å

  • c = 22.994 (2) Å

  • V = 1833.0 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 293 K

  • 0.30 × 0.20 × 0.20 mm

2.2. Data collection

  • Oxford Diffraction Xcalibur Sapphire3 diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]) Tmin = 0.865, Tmax = 1.000

  • 5318 measured reflections

  • 3554 independent reflections

  • 2457 reflections with I > 2σ(I)

  • Rint = 0.021

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.052

  • wR(F2) = 0.115

  • S = 1.02

  • 3554 reflections

  • 226 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.12 e Å−3

  • Δρmin = −0.14 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O2—H2⋯O1 0.88 (3) 2.06 (4) 2.628 (3) 122 (3)
O3—H3⋯O2i 0.82 2.46 3.203 (3) 151
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z].

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

CCDC reference: 1405794

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S2056989015011214/lh5767sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015011214/lh5767Isup2.hkl

checkCIF report


Comment top

In a continuation of our investigations on Otostegiafruticosa (Al-Musayeib et al., 2000) we report herein the isolation of Labdanediterpene, 15,16-epoxy-7β,9α-dihydroxylabdane- 13 (16),14-dien-6-one, from aerial parts of O. fruticosa. The structure of the isolate was established by spectral analysis followed by single crystal X-ray diffraction studies. The genus Otostegia (Labiatae) comprises 20 species (Shaw 1985), of which Otostegiafruticosa Forssk (Briq) is the only one found in Saudi Arabia. The plant of O. fruticosa is usually an erect, branched and straggly shrub with white flowers, up to 1.25 m in height. In Saudi Arabia, the plant grows on the rocky hills along the Jeddah-Taif road and Abha, where it is locally named Hewaymid and traditionally used as a remedy for sun-stroke (Mossa et al., 2000), and as mosquito repellent (Kidane et al., 2013). The molecular structure of the title compound (I) is shown in Fig. 1. The bond distances are in the normal ranges. The presence of the double bond C6═O1 is confirmed by the distance of 1.213 (3) Å. The torsion angle about the C11—C12 bond is 178.7 (2)°, indicating a trans conformation. Both cyclohexane rings adopts chair conformations. For cyclohexane ring (C5–C10), the best mirror plane passes through atoms C9 and C6 and the best two fold rotational axis bisects the C7—C10 bond with asymmetry parameters: [ΔCs(C9)=0.86 and ΔC2(C7—C8)=0.64] and in the case of ring (C1—C5/C10) the best mirror plane passes through the atoms C2 and C5 and the best two fold rotation axis bisects the C2—C3 bond with asymmetry parameters: [ΔCs(C2)=2.42 and ΔC2(C2—C3)=1.85]. There is an O—H···O intramolecular hydrogen bond between the hydroxyl groups containing atoms O2 and O1 via H2 which results in the formation of a pseudo five membered ring comprising of atoms O1/C6/C7/O2/H2 with S(5) graph-set motif. In the crystal, molecules are connected via O—H···O hydrogen bonds, forming chains along [100] (Fig. 2).

Related literature top

For background to the title compound, see: Al-Musayeib et al. (2000); Shaw (1985). For its biological activities, see: Mossa et al. (2000); Kidane et al. (2013). For the synthesis and spectroscopic data, see: Savona et al. (1976,1977); Hon et al. (1993).

Experimental top

Isolated areial parts of O. fruticosa were collected in the pre-flowering stage, in April, near the city of Abha, located in the Southern region of Saudi Arabia. A Voucher specimen has been deposited in the herbarium of Research Center for Medicinal, Aromatic and Poisonous Plants of College of Pharmacy, King Saud university. Air-dried and powdered aerial parts (500g) of O. fruticosa were exhaustively percolated with neutral, acetic acid-free, ethyl acetate. The solvent was evaporated and the residue was partitioned between acetonitrileand n-hexane, pre-saturated with each other. The combined hexane phases were back-washed with 100 ml of acetonitrile and combined acetonitrile phases were evaporated in vacuo to leave a greenish oily residue. A portion of acetonitrile fraction obtained above (5 g) was subjected to flash chromatography on a column (40 x 2.5 cm) of a silica gel and elution was carried in increasing polarity with n-hexane, 10% ether in hexane, 15% ether in hexane, 20% ether in hexane, and ether. Fractions got eluted in 20% ether in hexane were pooled, concentrated and residue on crystallization from n-hexane yielded LabdanediterpeneI. The title compound was obtained as fine needles, m.p 369.2 - 370.2K (from n-hexane). The molecular formula was established as C20H30O4 by EI mass spectrum and elemental analysis. The fragments at m/z 81 and 95 in the mass spectrum were indicative of presence of β-monosubstituted furan ring (Savona et al., 1977;1977). IR spectrum showed the presence of hydroxyl group (3520–3428 cm-1), α, β-unsaturated ketone (1695 cm-1) and an aromatic olefinic (1575 cm-1). The 1H NMR spectrum of I was consistent with a typical β-monosubstituted furan ring, as it contained two α-furan protons with resonance at δ 7.36 (brs, H-14) and δ 7.42 (brs, H-16) and one furan proton with a resonances δ 6.27 (brs, H-14). The 1H and 13 C NMR data contained resonances attributable to three tertiary methyl singlets (δH0.96, 1.29, 0.88; δC32.5, 22.2, 18.0), one secondary methyl group (δH1.25, d, J=6.5 Hz; δC12.3), five methylene, six methines, one of which is oxygen-bearing (δC77.1) and three of which were attributed to the β-substituted furan ring, and five quaternary carbon signals, including a ketonic carbonyl (δC211.9) and a tertiary hydroxyl-bearing carbon atom (δC77.4). The other physical and spectroscopy data is in good agreement with the literature (Hon et al., 1993).

Refinement top

H2 attached to O2 was located from a difference Fourier map and refined isotropically. The remaining H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93–0.98 Å, O2—H2 = 0.82Å and with Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(Cmethyl,O).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with ellipsoids drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii and the dashed line indicates an intramolecular hydrogen bond.
[Figure 2] Fig. 2. The packing arrangement of molecules viewed along the b axis. Hydrogen bonds are shown as dashed lines.
15,16-Epoxy-7β,9α-dihydroxylabdane-13 (16),14-dien-6-one top
Crystal data top
C20H30O4F(000) = 728
Mr = 334.44Dx = 1.212 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abθ = 4.2–27.3°
a = 8.5757 (7) ŵ = 0.08 mm−1
b = 9.2957 (8) ÅT = 293 K
c = 22.994 (2) ÅBlock, white
V = 1833.0 (3) Å30.30 × 0.20 × 0.20 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur Sapphire3
diffractometer		3554 independent reflections
Radiation source: fine-focus sealed tube2457 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
Detector resolution: 16.1049 pixels mm-1θmax = 26.0°, θmin = 3.5°
ω scansh = −10→6
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)		k = −11→9
Tmin = 0.865, Tmax = 1.000l = −14→28
5318 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)] = 0.052H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.115 w = 1/[σ2(Fo2) + (0.0448P)2 + 0.067P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
3554 reflectionsΔρmax = 0.12 e Å−3
226 parametersΔρmin = −0.14 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0048 (14)
Crystal data top
C20H30O4V = 1833.0 (3) Å3
Mr = 334.44Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.5757 (7) ŵ = 0.08 mm−1
b = 9.2957 (8) ÅT = 293 K
c = 22.994 (2) Å0.30 × 0.20 × 0.20 mm
Data collection top
Oxford Diffraction Xcalibur Sapphire3
diffractometer		3554 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)		2457 reflections with I > 2σ(I)
Tmin = 0.865, Tmax = 1.000Rint = 0.021
5318 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0520 restraints
wR(F2) = 0.115H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.12 e Å−3
3554 reflectionsΔρmin = −0.14 e Å−3
226 parameters
Special details top

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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 > σ(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
O30.31780 (19)0.20597 (18)0.05469 (7)0.0475 (5)
H30.30660.25230.02460.071*
C90.2680 (3)0.2912 (3)0.10343 (10)0.0346 (5)
C100.2913 (2)0.1911 (3)0.15784 (10)0.0342 (6)
C50.1913 (3)0.0511 (3)0.14935 (10)0.0359 (6)
H50.22470.01300.11160.043*
C10.4627 (3)0.1443 (3)0.16192 (12)0.0477 (7)
H1A0.49660.11270.12380.057*
H1B0.52510.22740.17240.057*
C60.0239 (3)0.0936 (3)0.14021 (11)0.0412 (6)
O2−0.1636 (2)0.2232 (3)0.08150 (12)0.0757 (7)
O1−0.0871 (2)0.0563 (2)0.16925 (8)0.0650 (6)
C80.0939 (3)0.3308 (3)0.09553 (11)0.0422 (6)
H80.05920.37990.13090.051*
C110.3672 (3)0.4308 (3)0.10900 (10)0.0436 (6)
H11A0.29810.50950.11920.052*
H11B0.44010.41840.14080.052*
C120.4588 (3)0.4737 (3)0.05478 (12)0.0598 (8)
H12A0.53090.39710.04490.072*
H12B0.38710.48540.02250.072*
C170.0631 (3)0.4306 (3)0.04419 (13)0.0634 (8)
H17A0.10230.38740.00920.095*
H17B0.11470.52090.05060.095*
H17C−0.04710.44640.04040.095*
C40.2190 (3)−0.0753 (3)0.19275 (11)0.0488 (7)
C7−0.0025 (3)0.1927 (3)0.08904 (12)0.0487 (7)
H70.03390.14290.05400.058*
C200.2425 (3)0.2737 (3)0.21285 (10)0.0457 (7)
H20A0.13200.26440.21840.068*
H20B0.26880.37350.20850.068*
H20C0.29610.23480.24590.068*
C20.4949 (3)0.0249 (3)0.20529 (14)0.0648 (9)
H2A0.6042−0.00170.20340.078*
H2B0.47330.05920.24430.078*
O40.6221 (3)0.8402 (3)0.05881 (12)0.1051 (9)
C30.3952 (3)−0.1058 (3)0.19269 (14)0.0638 (8)
H3A0.4174−0.17900.22160.077*
H3B0.4243−0.14420.15500.077*
C130.5481 (3)0.6103 (3)0.06312 (12)0.0541 (8)
C180.1353 (4)−0.2094 (3)0.16993 (14)0.0689 (9)
H18A0.1656−0.22660.13030.103*
H18B0.0246−0.19480.17180.103*
H18C0.1632−0.29090.19340.103*
C190.1641 (4)−0.0495 (3)0.25525 (11)0.0653 (9)
H19A0.1759−0.13630.27740.098*
H19B0.0563−0.02140.25500.098*
H19C0.22550.02550.27250.098*
C140.6804 (4)0.6324 (4)0.09808 (14)0.0708 (9)
H140.73110.56260.12000.085*
C160.5176 (5)0.7401 (4)0.04063 (15)0.0877 (12)
H160.43500.75940.01560.105*
C150.7203 (4)0.7698 (4)0.09435 (15)0.0841 (11)
H150.80430.81150.11360.101*
H2−0.195 (4)0.203 (4)0.1169 (13)0.076 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0644 (11)0.0427 (11)0.0354 (9)−0.0007 (10)0.0092 (8)−0.0046 (8)
C90.0398 (12)0.0324 (14)0.0317 (12)−0.0025 (12)0.0025 (10)−0.0027 (10)
C100.0322 (11)0.0365 (14)0.0337 (13)−0.0049 (11)0.0018 (10)0.0005 (10)
C50.0356 (12)0.0343 (14)0.0377 (13)−0.0017 (12)−0.0004 (11)−0.0019 (11)
C10.0355 (13)0.0496 (17)0.0581 (17)−0.0036 (13)−0.0021 (12)0.0088 (14)
C60.0405 (13)0.0324 (15)0.0509 (16)−0.0077 (13)−0.0044 (12)−0.0072 (11)
O20.0461 (11)0.0863 (19)0.0947 (19)−0.0021 (12)−0.0218 (12)0.0208 (14)
O10.0430 (10)0.0689 (15)0.0832 (14)−0.0102 (11)0.0058 (10)0.0128 (12)
C80.0454 (13)0.0374 (16)0.0437 (15)0.0028 (13)−0.0043 (12)−0.0006 (11)
C110.0549 (15)0.0384 (16)0.0375 (14)−0.0099 (14)0.0024 (12)−0.0008 (12)
C120.077 (2)0.055 (2)0.0471 (16)−0.0151 (17)0.0081 (15)0.0007 (14)
C170.0685 (18)0.054 (2)0.068 (2)−0.0020 (18)−0.0158 (15)0.0139 (15)
C40.0489 (14)0.0418 (18)0.0556 (17)−0.0050 (14)−0.0046 (13)0.0104 (13)
C70.0411 (14)0.0544 (19)0.0507 (16)−0.0001 (14)−0.0141 (12)−0.0001 (13)
C200.0518 (14)0.0462 (17)0.0390 (14)−0.0087 (14)−0.0015 (12)−0.0012 (12)
C20.0417 (14)0.073 (2)0.079 (2)0.0017 (16)−0.0102 (16)0.0243 (17)
O40.134 (2)0.0734 (18)0.1079 (19)−0.0477 (18)−0.0138 (19)0.0282 (16)
C30.0555 (16)0.051 (2)0.085 (2)0.0089 (16)−0.0046 (16)0.0230 (16)
C130.0673 (18)0.0552 (19)0.0396 (15)−0.0193 (16)0.0063 (14)0.0062 (14)
C180.078 (2)0.0350 (18)0.094 (2)−0.0063 (17)−0.0047 (18)0.0069 (16)
C190.0691 (18)0.071 (2)0.0562 (19)−0.0155 (19)0.0009 (16)0.0186 (16)
C140.0682 (19)0.074 (3)0.070 (2)−0.011 (2)−0.0080 (17)0.0168 (18)
C160.103 (3)0.075 (3)0.085 (3)−0.037 (2)−0.030 (2)0.032 (2)
C150.085 (2)0.090 (3)0.077 (2)−0.043 (2)−0.010 (2)0.008 (2)
Geometric parameters (Å, º) top
O3—C91.438 (3)C17—H17B0.9600
O3—H30.8200C17—H17C0.9600
C9—C81.548 (3)C4—C181.531 (4)
C9—C111.556 (3)C4—C191.531 (4)
C9—C101.572 (3)C4—C31.537 (3)
C10—C11.536 (3)C7—H70.9800
C10—C201.538 (3)C20—H20A0.9600
C10—C51.571 (3)C20—H20B0.9600
C5—C61.504 (3)C20—H20C0.9600
C5—C41.560 (3)C2—C31.514 (4)
C5—H50.9800C2—H2A0.9700
C1—C21.518 (4)C2—H2B0.9700
C1—H1A0.9700O4—C151.344 (4)
C1—H1B0.9700O4—C161.358 (4)
C6—O11.213 (3)C3—H3A0.9700
C6—C71.511 (4)C3—H3B0.9700
O2—C71.421 (3)C13—C161.339 (4)
O2—H20.88 (3)C13—C141.406 (4)
C8—C171.525 (4)C18—H18A0.9600
C8—C71.534 (4)C18—H18B0.9600
C8—H80.9800C18—H18C0.9600
C11—C121.527 (3)C19—H19A0.9600
C11—H11A0.9700C19—H19B0.9600
C11—H11B0.9700C19—H19C0.9600
C12—C131.495 (4)C14—C151.325 (4)
C12—H12A0.9700C14—H140.9300
C12—H12B0.9700C16—H160.9300
C17—H17A0.9600C15—H150.9300
C9—O3—H3109.5C18—C4—C3108.1 (2)
O3—C9—C8109.01 (18)C19—C4—C3109.4 (2)
O3—C9—C11111.19 (17)C18—C4—C5108.8 (2)
C8—C9—C11109.78 (19)C19—C4—C5115.8 (2)
O3—C9—C10104.86 (18)C3—C4—C5106.8 (2)
C8—C9—C10110.88 (18)O2—C7—C6111.2 (2)
C11—C9—C10111.01 (18)O2—C7—C8111.7 (2)
C1—C10—C20110.6 (2)C6—C7—C8110.69 (19)
C1—C10—C5107.2 (2)O2—C7—H7107.7
C20—C10—C5111.54 (18)C6—C7—H7107.7
C1—C10—C9109.75 (18)C8—C7—H7107.7
C20—C10—C9108.94 (19)C10—C20—H20A109.5
C5—C10—C9108.79 (17)C10—C20—H20B109.5
C6—C5—C4115.7 (2)H20A—C20—H20B109.5
C6—C5—C10108.70 (19)C10—C20—H20C109.5
C4—C5—C10117.47 (18)H20A—C20—H20C109.5
C6—C5—H5104.5H20B—C20—H20C109.5
C4—C5—H5104.5C3—C2—C1111.0 (2)
C10—C5—H5104.5C3—C2—H2A109.4
C2—C1—C10114.9 (2)C1—C2—H2A109.4
C2—C1—H1A108.5C3—C2—H2B109.4
C10—C1—H1A108.5C1—C2—H2B109.4
C2—C1—H1B108.5H2A—C2—H2B108.0
C10—C1—H1B108.5C15—O4—C16105.5 (3)
H1A—C1—H1B107.5C2—C3—C4114.0 (3)
O1—C6—C5126.6 (2)C2—C3—H3A108.7
O1—C6—C7119.0 (2)C4—C3—H3A108.7
C5—C6—C7114.3 (2)C2—C3—H3B108.7
C7—O2—H298 (2)C4—C3—H3B108.7
C17—C8—C7109.9 (2)H3A—C3—H3B107.6
C17—C8—C9113.7 (2)C16—C13—C14104.3 (3)
C7—C8—C9109.4 (2)C16—C13—C12128.0 (3)
C17—C8—H8107.9C14—C13—C12127.6 (3)
C7—C8—H8107.9C4—C18—H18A109.5
C9—C8—H8107.9C4—C18—H18B109.5
C12—C11—C9115.6 (2)H18A—C18—H18B109.5
C12—C11—H11A108.4C4—C18—H18C109.5
C9—C11—H11A108.4H18A—C18—H18C109.5
C12—C11—H11B108.4H18B—C18—H18C109.5
C9—C11—H11B108.4C4—C19—H19A109.5
H11A—C11—H11B107.4C4—C19—H19B109.5
C13—C12—C11112.4 (2)H19A—C19—H19B109.5
C13—C12—H12A109.1C4—C19—H19C109.5
C11—C12—H12A109.1H19A—C19—H19C109.5
C13—C12—H12B109.1H19B—C19—H19C109.5
C11—C12—H12B109.1C15—C14—C13108.2 (3)
H12A—C12—H12B107.9C15—C14—H14125.9
C8—C17—H17A109.5C13—C14—H14125.9
C8—C17—H17B109.5C13—C16—O4111.7 (3)
H17A—C17—H17B109.5C13—C16—H16124.1
C8—C17—H17C109.5O4—C16—H16124.1
H17A—C17—H17C109.5C14—C15—O4110.3 (3)
H17B—C17—H17C109.5C14—C15—H15124.8
C18—C4—C19107.7 (2)O4—C15—H15124.8
O3—C9—C10—C158.2 (2)C10—C9—C11—C12133.9 (2)
C8—C9—C10—C1175.7 (2)C9—C11—C12—C13178.7 (2)
C11—C9—C10—C1−62.0 (3)C6—C5—C4—C1860.4 (3)
O3—C9—C10—C20179.43 (17)C10—C5—C4—C18−169.0 (2)
C8—C9—C10—C20−63.1 (2)C6—C5—C4—C19−61.1 (3)
C11—C9—C10—C2059.3 (2)C10—C5—C4—C1969.5 (3)
O3—C9—C10—C5−58.8 (2)C6—C5—C4—C3176.8 (2)
C8—C9—C10—C558.7 (2)C10—C5—C4—C3−52.5 (3)
C11—C9—C10—C5−178.96 (18)O1—C6—C7—O2−2.5 (3)
C1—C10—C5—C6−175.4 (2)C5—C6—C7—O2177.4 (2)
C20—C10—C5—C663.4 (2)O1—C6—C7—C8122.3 (3)
C9—C10—C5—C6−56.8 (2)C5—C6—C7—C8−57.8 (3)
C1—C10—C5—C450.9 (3)C17—C8—C7—O2−54.3 (3)
C20—C10—C5—C4−70.3 (3)C9—C8—C7—O2−179.9 (2)
C9—C10—C5—C4169.49 (19)C17—C8—C7—C6−178.8 (2)
C20—C10—C1—C271.2 (3)C9—C8—C7—C655.6 (3)
C5—C10—C1—C2−50.6 (3)C10—C1—C2—C355.8 (3)
C9—C10—C1—C2−168.6 (2)C1—C2—C3—C4−57.4 (3)
C4—C5—C6—O112.5 (4)C18—C4—C3—C2171.0 (2)
C10—C5—C6—O1−122.2 (3)C19—C4—C3—C2−72.0 (3)
C4—C5—C6—C7−167.4 (2)C5—C4—C3—C254.1 (3)
C10—C5—C6—C757.9 (3)C11—C12—C13—C16−107.2 (4)
O3—C9—C8—C17−66.3 (3)C11—C12—C13—C1470.4 (4)
C11—C9—C8—C1755.7 (3)C16—C13—C14—C15−0.2 (4)
C10—C9—C8—C17178.7 (2)C12—C13—C14—C15−178.3 (3)
O3—C9—C8—C757.0 (2)C14—C13—C16—O40.5 (4)
C11—C9—C8—C7179.04 (19)C12—C13—C16—O4178.5 (3)
C10—C9—C8—C7−57.9 (3)C15—O4—C16—C13−0.5 (4)
O3—C9—C11—C1217.6 (3)C13—C14—C15—O4−0.1 (4)
C8—C9—C11—C12−103.1 (2)C16—O4—C15—C140.4 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O10.88 (3)2.06 (4)2.628 (3)122 (3)
O3—H3···O2i0.822.463.203 (3)151
Symmetry code: (i) x+1/2, −y+1/2, −z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O10.88 (3)2.06 (4)2.628 (3)122 (3)
O3—H3···O2i0.822.463.203 (3)151
Symmetry code: (i) x+1/2, −y+1/2, −z.
 

Acknowledgements

RK acknowledges the Department of Science & Technology for single-crystal X-ray diffractometer sanctioned as a National Facility under Project No. SR/S2/CMP-47/2003.

References

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ISSN: 2056-9890
Volume 71| Part 7| July 2015| Pages o483-o484
doi:10.1107/S2056989015011214
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