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Acta Cryst. (2007). E63, o3948    [ doi:10.1107/S1600536807042201 ]

Isocedrelone

S. S. Devi, R. Malathi, S. S. Rajan, V. P. Santhanakrishnan and S. Narasimhan

Abstract top

The title compound (systematic name: 17-furan-3-yl-6,15-dihydroxy-4,4,8,10,14-pentamethyl-8,9,10,11,12,14,15,16-octahydro-4H-cyclopenta[a]phenanthrene-3,7-dione), C26H30O5, is a semi-synthetic derivative of cedrelone, a tetranortriterpenoid isolated from Toona ciliata. Both cedrelone and the title compound show similar antifeedant activity against third instar larvae of Spodoptera litura. The modification of the D ring of the parent compound has altered the conformation of ring C; however, the orientation of the furan ring as well as the conformations of other rings remain the same. The three fused six-membered rings adopt a boat, a half-chair and a chair conformation and the five-membered rings D and E adopt envelope and planar conformations, respectively. A macrocyclic ring motif, R76(40), S(5) and S(7), generated by C-H...O and O-H...O hydrogen bonds, stabilizes the molecules in the crystal structure.

Comment top

An intact limonoid Cedrelone, has been previously isolated from Toona ciliata and its three dimensional structure was reported earlier (Zeumer et al., 2000). It possess half the antifeedant activity of the most potent, Azadirachtin–A from Azadirachta indica. The title compound, a semisynthetic derivative of cedrelone differs chemically from the parent molecule by the modification of ring D. Abstraction of C17 proton has resulted in the shift of C13 methyl group to C14, opening up of epoxide ring between C14—C15, formation of hydroxyl at C15 and the double bond between C13═C17. This modification has altered the ring conformations and the orientation of furan ring with respect to ring D is C16—C17—C20—C22 = 164.1 (5)° for (I) and 168.3 (4)° for cedrelone, compared with parent compound (Zeumer et al., 2000);

Ring A [QT = 0.522 (4) Å, φ2 = −68.6 (5)°, q2 = 0.515 (4) Å] is in a boat conformation. The atoms C1 and C10 deviate by 0.165 (4)Å and 0.734 (3)Å from the plane involving the other four atoms of the ring. Ring B [QT = 0.418 (3) Å, φ2 = −138.4 (6)°, q2 = 0.331 (3) Å] adopts a half–chair conformation as in cedrelone (Zeumer et al., 2000). The atoms C8 and C9 deviate from the LSQ–plane of the other four atoms by 0.209 (3)Å and −0.427 (3)Å respectively. Ring C takes up a chair conformation [QT = 0.586 (4) Å, φ2 = −4.85(8.12)°, q2 =0.027 (4) Å] with atoms C8 and C12 deviating from the plane by 0.717 (3)Å and −0.667 (4)Å respectively from the plane of other four atoms of the ring. It adopts a twist conformation in cedrelone. Rings D and E are in an envelope [φ2 = 70.23(1.12)°, q2 = 0.205 (4)Å for ring D] and a planar conformation (Nardelli, 1995) respectively (Cremer & Pople, 1975).

Ring motifs are generated through O—H···O and C—H···O hydrogen bonds in the crystal lattice (Fig 2). Two ring motifs S(5) and S(7) are genereated through hydrogen bonds O6—H6···O7 and O15—H15A···O7 respectively. A macrocyclic ring motif R76[40] (Bernstein et al., 1995) is generated through hydrogen bonds C11—H11A···O3 [2 − x, −1/2 + y, 3/2 − z] and C19—H11B···O7 [3/2 − x, 2 − y, −1/2 + z].

Related literature top

Several cedrelone derivatives have been synthesized through classical chemical modifications and the crystal structures of cedrelone (Zeumer et al., 2000) and a few derivatives have been reported. For related literature, see: Bernstein et al. (1995); Cremer & Pople (1975); Flack (1983); Narayanan et al. (1980).

Experimental top

To a solution of Cedrelone (40 mg, 0.085 mmol) in acetone (3 ml) 400 mg of the freshly prepared N–bromoacetamide resin was added and placed under the microwave with stirring for 3 min. The reaction was monitored by TLC using Ethylacetate and hexane in the ratio 1:1). The resin was then filtered and was washed three times with 2 ml of acetone. The solvent was removed under reduced pressure. The crude product was chromotographed on silica gel (70–325 mesh) using an eluant ethylacetate and hexane, in the increasing order of polarity. Elution of the column using ethylacetate/hexane = 10/90 yielded compound (I).

Refinement top

In the absence of suitable anomalous scatters, Friedel equivalents could not be used to determine the absolute structure. Refinement of the Flack parameter (Flack, 1983) led to inconclusive values (Flack & Bernardinelli, 2000) for this parameter [1(3)]. Therefore, 3557 Friedel equivalents were merged before the final refinement. The enantiomer employed in the refined model was chosen to agree with the accepted configuration of tetranortriterpenoids (Narayanan et al., 1980).

The C—H and CH2, atoms were constrained to an ideal geometry (CH = 0.98, CH2 = 0.97, OH = 0.82 Å) with Uiso(H) = 1.2Ueq(C), but where allowed to rotate freely about the C—C and C—O bonds, respectively. For CH3 and OH, hydrogen atoms were constrained to ride on their parent atom with Uiso(H) = 1.5Ueq(parent atom).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PARST97 (Nardelli, 1995).

Figures top
[Figure 1] Fig. 1. Molecular structure and atomic numbering schemeof (I) with 30% probability displacement ellipsoids and atomic numbering scheme. The H atoms are presented as a spheres of arbitrary radius.
[Figure 2] Fig. 2. A view of the crystal packing of (I) view down 'b' axis with the hydrogen bonds. Hydrogen atoms not involved in hydrogen bonds have been omitted for clarity.
17-furan-3-yl-6,15-dihydroxy-4,4,8,10,14-pentamethyl-8,9,10,11,12,14,15,16- octahydro-4H-cyclopenta[a]phenanthrene-3,7-dione top
Crystal data top
C26H30O5F000 = 904
Mr = 422.50Dx = 1.284 Mg m−3
Orthorhombic, P212121Mo Kα radiation
λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 11.639 (4) Åθ = 5–11º
b = 13.027 (2) ŵ = 0.09 mm−1
c = 14.417 (5) ÅT = 293 (2) K
V = 2185.9 (11) Å3Prism, yellow
Z = 40.23 × 0.21 × 0.21 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer		Rint = 0.022
Radiation source: fine–focus sealed tubeθmax = 30.0º
Monochromator: graphiteθmin = 2.1º
T = 293(2) Kh = 0→16
ω scansk = 0→18
Absorption correction: nonel = −1→20
3810 measured reflections3 standard reflections
3557 independent reflections every 120 reflections
1738 reflections with I > 2σ(I) intensity decay: 2%
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.059  w = 1/[σ2(Fo2) + (0.0895P)2 + 0.3096P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.188(Δ/σ)max = 0.042
S = 1.02Δρmax = 0.20 e Å−3
3557 reflectionsΔρmin = −0.23 e Å−3
287 parametersExtinction correction: none
1 restraint
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Crystal data top
C26H30O5V = 2185.9 (11) Å3
Mr = 422.50Z = 4
Orthorhombic, P212121Mo Kα
a = 11.639 (4) ŵ = 0.09 mm−1
b = 13.027 (2) ÅT = 293 (2) K
c = 14.417 (5) Å0.23 × 0.21 × 0.21 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer		Rint = 0.022
Absorption correction: none3 standard reflections
3810 measured reflections every 120 reflections
3557 independent reflections intensity decay: 2%
1738 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.059H-atom parameters constrained
wR(F2) = 0.188Δρmax = 0.20 e Å−3
S = 1.02Δρmin = −0.23 e Å−3
3557 reflectionsAbsolute structure: ?
287 parametersFlack parameter: ?
1 restraintRogers parameter: ?
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 > 2σ(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
C10.8295 (5)1.1629 (3)0.8368 (3)0.0636 (11)
H10.75811.14660.81180.076*
C20.8688 (5)1.2571 (3)0.8284 (3)0.0790 (14)
H20.82651.30610.79600.095*
C30.9800 (6)1.2848 (4)0.8704 (4)0.0847 (16)
C41.0118 (4)1.2324 (3)0.9612 (3)0.0623 (11)
C50.9509 (3)1.1291 (3)0.9719 (3)0.0502 (9)
C60.9440 (3)1.0809 (3)1.0537 (3)0.0537 (9)
C70.8920 (3)0.9804 (3)1.0695 (2)0.0497 (9)
C80.8527 (3)0.9158 (3)0.9891 (2)0.0428 (8)
C90.8120 (3)0.9916 (3)0.9116 (2)0.0427 (8)
H90.74441.02620.93750.051*
C100.8975 (3)1.0802 (3)0.8861 (2)0.0486 (9)
C110.7683 (4)0.9354 (3)0.8260 (3)0.0570 (10)
H11A0.83070.89660.79860.068*
H11B0.74200.98510.78060.068*
C120.6694 (4)0.8622 (3)0.8501 (3)0.0641 (11)
H12A0.60310.90100.87100.077*
H12B0.64740.82300.79570.077*
C130.7087 (3)0.7923 (3)0.9242 (3)0.0499 (9)
C140.7492 (3)0.8424 (3)1.0148 (2)0.0464 (8)
C150.7747 (4)0.7430 (3)1.0737 (3)0.0588 (10)
H150.70500.72931.10980.071*
C160.7876 (4)0.6542 (3)1.0074 (3)0.0621 (11)
H16A0.86800.63890.99620.075*
H16B0.74990.59331.03110.075*
C170.7301 (3)0.6918 (3)0.9207 (3)0.0530 (9)
C180.6518 (3)0.9029 (3)1.0623 (3)0.0620 (11)
H18A0.68010.93311.11860.093*
H18B0.58940.85731.07640.093*
H18C0.62530.95611.02150.093*
C190.9946 (4)1.0471 (3)0.8182 (3)0.0697 (13)
H19A0.96121.01560.76430.105*
H19B1.04440.99890.84850.105*
H19C1.03801.10630.79980.105*
C200.7107 (4)0.6200 (3)0.8442 (3)0.0631 (12)
C210.7550 (9)0.5260 (4)0.8367 (5)0.128 (3)
H210.80240.49720.88170.153*
C220.6395 (6)0.6265 (5)0.7665 (4)0.107 (2)
H220.59350.68270.75200.128*
C230.6464 (7)0.5425 (5)0.7167 (4)0.116 (2)
H230.60590.52890.66250.139*
C280.9729 (5)1.3119 (4)1.0330 (4)0.0911 (17)
H28A1.01411.37491.02340.137*
H28B0.98831.28651.09430.137*
H28C0.89201.32411.02630.137*
C291.1425 (5)1.2162 (4)0.9664 (5)0.1022 (19)
H29A1.18071.28120.96030.153*
H29B1.16631.17150.91710.153*
H29C1.16201.18591.02500.153*
C300.9592 (3)0.8524 (3)0.9602 (3)0.0559 (10)
H30A0.93980.80900.90870.084*
H30B0.98380.81081.01150.084*
H30C1.02020.89810.94260.084*
O31.0399 (5)1.3534 (3)0.8388 (3)0.1323 (18)
O60.9912 (3)1.1237 (3)1.1320 (2)0.0848 (10)
H60.98561.08321.17530.127*
O70.8893 (3)0.9497 (2)1.15122 (18)0.0684 (8)
O150.8667 (3)0.7449 (3)1.1382 (2)0.0868 (10)
H15A0.87980.80441.15350.130*
O230.7255 (6)0.4771 (4)0.7596 (4)0.145 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.094 (3)0.050 (2)0.047 (2)0.004 (2)0.000 (2)0.0076 (18)
C20.129 (4)0.051 (2)0.057 (2)0.009 (3)−0.008 (3)0.011 (2)
C30.125 (5)0.057 (3)0.072 (3)−0.012 (3)0.022 (3)0.001 (2)
C40.069 (3)0.061 (2)0.057 (2)−0.012 (2)0.010 (2)−0.002 (2)
C50.054 (2)0.052 (2)0.0448 (19)−0.0050 (18)0.0080 (17)−0.0054 (17)
C60.058 (2)0.062 (2)0.0413 (19)−0.0113 (19)−0.0026 (18)−0.0022 (19)
C70.050 (2)0.059 (2)0.0397 (19)0.0057 (18)−0.0008 (17)0.0058 (17)
C80.0473 (18)0.0443 (17)0.0366 (17)0.0033 (16)0.0003 (16)0.0054 (15)
C90.0503 (18)0.0411 (17)0.0367 (17)0.0062 (16)−0.0015 (15)0.0005 (15)
C100.064 (2)0.0459 (18)0.0356 (17)0.0067 (18)0.0051 (18)0.0027 (16)
C110.083 (3)0.051 (2)0.0370 (17)0.004 (2)−0.012 (2)0.0045 (17)
C120.076 (3)0.054 (2)0.062 (2)−0.004 (2)−0.031 (2)0.001 (2)
C130.052 (2)0.053 (2)0.045 (2)−0.0036 (17)−0.0008 (18)−0.0010 (17)
C140.0491 (19)0.0495 (19)0.0407 (18)−0.0018 (17)−0.0015 (17)0.0022 (16)
C150.065 (2)0.056 (2)0.055 (2)−0.006 (2)0.003 (2)0.014 (2)
C160.073 (3)0.048 (2)0.065 (3)0.001 (2)0.005 (2)0.013 (2)
C170.053 (2)0.049 (2)0.056 (2)−0.0058 (17)0.010 (2)−0.0003 (18)
C180.058 (2)0.068 (2)0.060 (2)−0.005 (2)0.014 (2)−0.007 (2)
C190.098 (3)0.060 (2)0.051 (2)−0.006 (2)0.033 (2)−0.004 (2)
C200.079 (3)0.045 (2)0.065 (3)−0.006 (2)0.020 (2)−0.002 (2)
C210.237 (9)0.064 (3)0.083 (4)0.021 (5)−0.003 (5)−0.014 (3)
C220.152 (6)0.089 (4)0.079 (4)0.009 (4)−0.020 (4)−0.019 (3)
C230.191 (7)0.092 (4)0.065 (3)−0.033 (4)0.014 (4)−0.042 (3)
C280.118 (4)0.065 (3)0.090 (4)−0.024 (3)0.019 (4)−0.024 (3)
C290.080 (4)0.091 (4)0.135 (5)−0.029 (3)0.020 (4)0.002 (4)
C300.050 (2)0.055 (2)0.063 (2)0.0057 (19)0.0064 (19)0.008 (2)
O30.187 (5)0.092 (3)0.118 (3)−0.064 (3)0.025 (3)0.035 (3)
O60.116 (3)0.088 (2)0.0506 (16)−0.032 (2)−0.0207 (19)−0.0003 (16)
O70.089 (2)0.0785 (19)0.0375 (14)−0.0127 (17)−0.0066 (14)0.0097 (13)
O150.106 (2)0.076 (2)0.078 (2)−0.011 (2)−0.036 (2)0.0305 (19)
O230.229 (6)0.085 (3)0.121 (4)−0.012 (3)0.024 (4)−0.022 (3)
Geometric parameters (Å, °) top
C1—C21.316 (6)C15—O151.419 (5)
C1—C101.514 (5)C15—C161.508 (6)
C1—H10.9300C15—H150.9800
C2—C31.475 (8)C16—C171.500 (6)
C2—H20.9300C16—H16A0.9700
C3—O31.222 (6)C16—H16B0.9700
C3—C41.522 (7)C17—C201.463 (6)
C4—C281.533 (6)C18—H18A0.9600
C4—C51.528 (6)C18—H18B0.9600
C4—C291.537 (7)C18—H18C0.9600
C5—C61.339 (5)C19—H19A0.9600
C5—C101.524 (5)C19—H19B0.9600
C6—O61.374 (5)C19—H19C0.9600
C6—C71.461 (6)C20—C211.334 (8)
C7—O71.245 (4)C20—C221.396 (7)
C7—C81.503 (5)C21—O231.327 (8)
C8—C301.546 (5)C21—H210.9300
C8—C91.565 (5)C22—C231.311 (7)
C8—C141.583 (5)C22—H220.9300
C9—C111.522 (5)C23—O231.399 (9)
C9—C101.567 (5)C23—H230.9300
C9—H90.9800C28—H28A0.9600
C10—C191.557 (5)C28—H28B0.9600
C11—C121.534 (6)C28—H28C0.9600
C11—H11A0.9700C29—H29A0.9600
C11—H11B0.9700C29—H29B0.9600
C12—C131.477 (5)C29—H29C0.9600
C12—H12A0.9700C30—H30A0.9600
C12—H12B0.9700C30—H30B0.9600
C13—C171.333 (5)C30—H30C0.9600
C13—C141.534 (5)O6—H60.8200
C14—C181.542 (5)O15—H15A0.8200
C14—C151.576 (5)
C2—C1—C10121.7 (5)C15—C14—C8118.6 (3)
C2—C1—H1119.1O15—C15—C16110.7 (4)
C10—C1—H1119.1O15—C15—C14118.8 (3)
C1—C2—C3119.7 (5)C16—C15—C14107.9 (3)
C1—C2—H2120.2O15—C15—H15106.2
C3—C2—H2120.2C16—C15—H15106.2
O3—C3—C2121.7 (5)C14—C15—H15106.2
O3—C3—C4120.7 (6)C17—C16—C15103.5 (3)
C2—C3—C4117.2 (4)C17—C16—H16A111.1
C3—C4—C28101.9 (4)C15—C16—H16A111.1
C3—C4—C5111.6 (4)C17—C16—H16B111.1
C28—C4—C5113.0 (3)C15—C16—H16B111.1
C3—C4—C29110.1 (4)H16A—C16—H16B109.0
C28—C4—C29110.6 (4)C13—C17—C20128.8 (4)
C5—C4—C29109.5 (4)C13—C17—C16111.9 (4)
C6—C5—C10119.6 (3)C20—C17—C16119.2 (3)
C6—C5—C4122.0 (4)C14—C18—H18A109.5
C10—C5—C4118.4 (3)C14—C18—H18B109.5
C5—C6—O6120.6 (3)H18A—C18—H18B109.5
C5—C6—C7125.7 (3)C14—C18—H18C109.5
O6—C6—C7113.7 (3)H18A—C18—H18C109.5
O7—C7—C6116.5 (4)H18B—C18—H18C109.5
O7—C7—C8122.9 (4)C10—C19—H19A109.5
C6—C7—C8120.5 (3)C10—C19—H19B109.5
C7—C8—C30105.2 (3)H19A—C19—H19B109.5
C7—C8—C9106.8 (3)C10—C19—H19C109.5
C30—C8—C9112.8 (3)H19A—C19—H19C109.5
C7—C8—C14112.9 (3)H19B—C19—H19C109.5
C30—C8—C14110.6 (3)C21—C20—C22102.7 (5)
C9—C8—C14108.5 (3)C21—C20—C17126.1 (5)
C11—C9—C8112.1 (3)C22—C20—C17131.1 (4)
C11—C9—C10112.1 (3)C20—C21—O23114.1 (7)
C8—C9—C10116.1 (3)C20—C21—H21122.9
C11—C9—H9105.1O23—C21—H21122.9
C8—C9—H9105.1C23—C22—C20110.7 (6)
C10—C9—H9105.1C23—C22—H22124.6
C5—C10—C1107.3 (3)C20—C22—H22124.7
C5—C10—C19109.3 (3)C22—C23—O23107.8 (6)
C1—C10—C19106.3 (3)C22—C23—H23126.1
C5—C10—C9112.2 (3)O23—C23—H23126.1
C1—C10—C9107.6 (3)C4—C28—H28A109.5
C19—C10—C9113.9 (3)C4—C28—H28B109.5
C9—C11—C12111.5 (3)H28A—C28—H28B109.5
C9—C11—H11A109.3C4—C28—H28C109.5
C12—C11—H11A109.3H28A—C28—H28C109.5
C9—C11—H11B109.3H28B—C28—H28C109.5
C12—C11—H11B109.3C4—C29—H29A109.5
H11A—C11—H11B108.0C4—C29—H29B109.5
C13—C12—C11108.3 (3)H29A—C29—H29B109.5
C13—C12—H12A110.0C4—C29—H29C109.5
C11—C12—H12A110.0H29A—C29—H29C109.5
C13—C12—H12B110.0H29B—C29—H29C109.5
C11—C12—H12B110.0C8—C30—H30A109.5
H12A—C12—H12B108.4C8—C30—H30B109.5
C17—C13—C12129.5 (4)H30A—C30—H30B109.5
C17—C13—C14113.1 (4)C8—C30—H30C109.5
C12—C13—C14116.7 (3)H30A—C30—H30C109.5
C13—C14—C18111.7 (3)H30B—C30—H30C109.5
C13—C14—C1599.7 (3)C6—O6—H6109.5
C18—C14—C15108.6 (3)C15—O15—H15A109.5
C13—C14—C8107.0 (3)C21—O23—C23104.4 (5)
C18—C14—C8110.8 (3)
C10—C1—C2—C3−2.1 (7)C11—C9—C10—C19−49.2 (4)
C1—C2—C3—O3152.4 (5)C8—C9—C10—C1981.3 (4)
C1—C2—C3—C4−34.0 (7)C8—C9—C11—C1257.4 (4)
O3—C3—C4—C2877.8 (6)C10—C9—C11—C12−170.0 (3)
C2—C3—C4—C28−95.9 (5)C9—C11—C12—C13−54.8 (4)
O3—C3—C4—C5−161.4 (5)C11—C12—C13—C17−110.9 (5)
C2—C3—C4—C524.9 (6)C11—C12—C13—C1458.4 (5)
O3—C3—C4—C29−39.6 (7)C17—C13—C14—C18−126.8 (4)
C2—C3—C4—C29146.7 (5)C12—C13—C14—C1862.1 (4)
C3—C4—C5—C6−164.1 (4)C17—C13—C14—C15−12.2 (4)
C28—C4—C5—C6−50.0 (6)C12—C13—C14—C15176.7 (3)
C29—C4—C5—C673.7 (5)C17—C13—C14—C8111.8 (4)
C3—C4—C5—C1016.3 (5)C12—C13—C14—C8−59.2 (4)
C28—C4—C5—C10130.4 (4)C7—C8—C14—C13172.8 (3)
C29—C4—C5—C10−105.9 (5)C30—C8—C14—C13−69.6 (4)
C10—C5—C6—O6−179.8 (4)C9—C8—C14—C1354.6 (4)
C4—C5—C6—O60.6 (6)C7—C8—C14—C1850.8 (4)
C10—C5—C6—C72.4 (6)C30—C8—C14—C18168.4 (3)
C4—C5—C6—C7−177.2 (4)C9—C8—C14—C18−67.3 (4)
C5—C6—C7—O7−177.1 (4)C7—C8—C14—C15−75.7 (4)
O6—C6—C7—O74.9 (5)C30—C8—C14—C1541.9 (4)
C5—C6—C7—C87.4 (6)C9—C8—C14—C15166.1 (3)
O6—C6—C7—C8−170.6 (4)C13—C14—C15—O15146.0 (4)
O7—C7—C8—C30−87.2 (4)C18—C14—C15—O15−97.0 (4)
C6—C7—C8—C3088.0 (4)C8—C14—C15—O1530.6 (5)
O7—C7—C8—C9152.7 (4)C13—C14—C15—C1619.1 (4)
C6—C7—C8—C9−32.1 (4)C18—C14—C15—C16136.1 (3)
O7—C7—C8—C1433.5 (5)C8—C14—C15—C16−96.3 (4)
C6—C7—C8—C14−151.3 (3)O15—C15—C16—C17−150.9 (3)
C7—C8—C9—C11−179.3 (3)C14—C15—C16—C17−19.4 (4)
C30—C8—C9—C1165.6 (4)C12—C13—C17—C20−6.3 (7)
C14—C8—C9—C11−57.3 (4)C14—C13—C17—C20−175.9 (4)
C7—C8—C9—C1050.1 (4)C12—C13—C17—C16170.2 (4)
C30—C8—C9—C10−65.0 (4)C14—C13—C17—C160.5 (5)
C14—C8—C9—C10172.1 (3)C15—C16—C17—C1312.1 (5)
C6—C5—C10—C1133.3 (4)C15—C16—C17—C20−171.1 (3)
C4—C5—C10—C1−47.0 (5)C13—C17—C20—C21164.9 (6)
C6—C5—C10—C19−111.8 (4)C16—C17—C20—C21−11.3 (8)
C4—C5—C10—C1967.8 (4)C13—C17—C20—C22−19.7 (8)
C6—C5—C10—C915.4 (5)C16—C17—C20—C22164.1 (5)
C4—C5—C10—C9−164.9 (3)C22—C20—C21—O234.7 (8)
C2—C1—C10—C541.0 (5)C17—C20—C21—O23−178.8 (5)
C2—C1—C10—C19−75.9 (5)C21—C20—C22—C23−2.0 (8)
C2—C1—C10—C9161.8 (4)C17—C20—C22—C23−178.2 (5)
C11—C9—C10—C5−174.0 (3)C20—C22—C23—O23−1.1 (8)
C8—C9—C10—C5−43.4 (4)C20—C21—O23—C23−5.5 (9)
C11—C9—C10—C168.3 (4)C22—C23—O23—C213.8 (8)
C8—C9—C10—C1−161.1 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O6—H6···O70.822.102.573 (4)117
O15—H15A···O70.821.902.687 (4)162
C11—H11A···O3i0.972.553.431 (6)151
C11—H11B···O7ii0.972.563.458 (5)155
Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) −x+3/2, −y+2, z−1/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O6—H6···O70.822.102.573 (4)117
O15—H15A···O70.821.902.687 (4)162
C11—H11A···O3i0.972.553.431 (6)151
C11—H11B···O7ii0.972.563.458 (5)155
Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) −x+3/2, −y+2, z−1/2.
Acknowledgements top

SSD thanks the University of Madras for a University Research Fellowship and RM thanks CSIR (India) for a Research Associateship.

references
References top

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