supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers buy article online

wn2196 scheme

Acta Cryst. (2007). E63, o3963    [ doi:10.1107/S1600536807042535 ]

1,2-Dihydrocedrelone

S. S. Devi, S. S. Rajan, R. M. Kumar and S. Narasimhan

Abstract top

The title compound (systematic name: 7-furan-3-yl-6-hydroxy-4,4,8,10,13-pentamethyl-1,8,9,10,11,12,13,15,16,17-decahydro-2H,4H-20-oxacyclopropa[14,15]cyclopenta[a]phenanthrene-3,7-dione), C26H32O5, is a semi-synthetic derivative of cedrelone, a natural compound isolated from Toona ciliata. The orientation of the furan ring and the ring conformations are the same as for cedrelone itself, with the exception of ring A. Rings A, B, C and D adopt sofa, half-chair, twist and envelope conformations, respectively. The crystal structure involves intramolecular O-H...O and intermolecular C-H...O and O-H...O hydrogen bonds. All the hydrogen bonds in the crystal structure contribute to the formation of a macrocyclic ring motif R44(28).

Comment top

A tetranortriterpenoid, cedrelone, has been previously isolated from Toona ciliata and its three dimensional structure was reported earlier (Zeumer et al., 2000). It possesses half the antifeedant activity of the most potent azadirachtin-A from Azadirachta indica. The title compound (Fig. 1), a semisynthetic derivative of cedrelone, differs from the parent molecule simply by having single bond C1—C2 rather than C1═C2. Except for ring A, the ring conformations in the title compound are the same as in cedrelone (Zeumer et al., 2000). The orientation of the furan ring is defined by the torsion angle C16—C17—C20—C22 = 179.8 (4)°; the corresponding value in cedrelone is 168.3 (4)°.

Ring A exists in a sofa conformation (Cremer & Pople, 1975) [QT = 0.688 (4) Å, φ2 = −48 (3)°, q2 = 0.677 (4) Å], and a mirror plane passes through atoms C3 and C10; in cedrelone itself, ring A adopts a distorted half-chair conformation. Ring B [QT =0.522 (4) Å, φ2=32.3 (5)°,q2 =0.435 (3) Å] adopts a half-chair conformation. Ring C adopts a twist conformation [QT =0.760 (3) Å, φ2 =88.1 (3) °, q2 =0.757 (3) Å]. The atoms C8 and C9 deviate from the mean plane of the other four atoms by 0.385 (3) Å and −0.407 (3) Å respectively. Ring D is in an envelope conformation [φ2 = −145.1 (3)°,q2 = 0.204 (4) Å] and ring E is planar (Nardelli, 1995). Ring pairs A/B, B/C and C/D are in quasi-trans fusion as evident from the endocyclic torsion angles of ring junction atoms. Thus, for rings A/B C4—C5—C10—C1 = −51.8 (4)° and C6—C5—C10—C9 = 9.8 (5)\5; for rings B/C C7—C8—C9—C10 = 63.5 (4)° and C14—C8—C9—C11 = −37.9 (4)°; for rings C/D C12—C13—C14—C8 = 58.5 (4)° and C17—C13—C14—C15 = −19.0 (4)°.

The packing of the molecules (Fig. 2) reveals that the crystal structure is stabilized by a network of hydrogen bonds (Table 1). The hydrogen bond C12—H12A···O15(−x + 2,y + 1/2,-z) forms an infinite chain, graph set motif C(9). A ring motif S(5) is formed by the hydrogen bond O6—H6···O7. In addition, R22(9) is generated through C2—H2A···O7(1 + x,y,z) and O6—H6···O3(−1 + x,y,z). All the observed hydrogen bonds in the crystal structure together form a macrocyclic ring motif R44(28).

Related literature top

Many cedrelone derivatives have been reported (Hodges et al., 1963). The three-dimensional structure of cedrelone itself has previously been reported (Zeumer et al., 2000). For related literature, see: Bernstein et al. (1995); Cremer & Pople (1975); Narayanan et al. (1980).

Experimental top

Acetic acid (5 ml) was placed in a 25 ml Erylenmeyer flask fitted with microwave and reflux condenser with guard tube. To this cedrelone (141 mg, 0.33 mmol) and activated zinc was added. The mixture was then subjected to microwave radiation. After completion of the reaction, the solution was passed through a celite bed, followed by acetic acid and was removed by vacuum distillation. The title compound was purified by short flash (under nitrogen) column chromatography.

Refinement top

In the absence of significant anomalous scattering effects, 2161 Friedel equivalents were merged. The enantiomer employed in the refined model was chosen to agree with the accepted configuration of tetranortriterpenoids (Narayanan et al., 1980).

Hydrogen atoms were positioned geometrically and constrained to ride on their parent atoms, with C—H = 0.93, 0.96, 0.97 and 0.98 Å for Csp2, methyl, methylene and methine, respectively; O—H = 0.82 Å. These C—H and O—H bonds were allowed to rotate freely about the C—C and C—O bonds. Uiso(H) = xUeq(carrier atom) where x = 1.5 for methyl and O, 1.2 for all other H atoms.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; 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 and PARST97 (Nardelli, 1995).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, with 30% probability displacement ellipsoids and the atomic numbering scheme. Hydrogen atoms have been omitted.
[Figure 2] Fig. 2. A view of the packing in the crystal structure, showing the R44(28) ring. Dashed lines indicate hydrogen bonding. H atoms not involved in hydrogen bonding have been omitted.
7-furan-3-yl-6-hydroxy-4,4,8,10,13-pentamethyl-1,8,9,10,11,12,13,15,16,17- decahydro-2H,4H-20-oxacyclopropa[14,15]cyclopenta[a]phenanthrene- 3,7-dione top
Crystal data top
C26H32O5F000 = 456
Mr = 424.52Dx = 1.239 Mg m−3
Monoclinic, P21Cu Kα radiation
λ = 1.54184 Å
a = 8.302 (4) ÅCell parameters from 25 reflections
b = 10.150 (2) Åθ = 15–30º
c = 13.560 (5) ŵ = 0.68 mm−1
β = 95.330 (3)ºT = 293 (2) K
V = 1137.7 (7) Å3Rod, colourless
Z = 20.30 × 0.23 × 0.21 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer		Rint = 0.087
Radiation source: fine-focus sealed tubeθmax = 67.5º
Monochromator: graphiteθmin = 3.3º
T = 293(2) Kh = 0→9
non–profiled ω/2θ scansk = 0→12
Absorption correction: nonel = −16→16
2591 measured reflections3 standard reflections
2161 independent reflections every 200 reflections
1974 reflections with I > 2σ(I) intensity decay: 3%
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.062  w = 1/[σ2(Fo2) + (0.199P)2 + 0.4014P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.189(Δ/σ)max < 0.001
S = 0.80Δρmax = 0.25 e Å−3
2161 reflectionsΔρmin = −0.34 e Å−3
286 parametersExtinction correction: none
1 restraint
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Crystal data top
C26H32O5V = 1137.7 (7) Å3
Mr = 424.52Z = 2
Monoclinic, P21Cu Kα
a = 8.302 (4) ŵ = 0.68 mm−1
b = 10.150 (2) ÅT = 293 (2) K
c = 13.560 (5) Å0.30 × 0.23 × 0.21 mm
β = 95.330 (3)º
Data collection top
Enraf–Nonius CAD-4
diffractometer		Rint = 0.087
Absorption correction: none3 standard reflections
2591 measured reflections every 200 reflections
2161 independent reflections intensity decay: 3%
1974 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.062H-atom parameters constrained
wR(F2) = 0.189Δρmax = 0.25 e Å−3
S = 0.80Δρmin = −0.34 e Å−3
2161 reflectionsAbsolute structure: ?
286 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 > 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
O31.5868 (3)0.4276 (5)0.4887 (2)0.0712 (11)
O60.9552 (3)0.3939 (4)0.4596 (2)0.0630 (9)
H60.85860.37580.45350.095*
O70.7759 (3)0.2519 (4)0.3276 (2)0.0597 (8)
O150.9023 (4)−0.0169 (3)0.1327 (2)0.0562 (8)
O230.4733 (4)0.2782 (4)−0.2042 (3)0.0756 (10)
C11.3541 (5)0.4167 (4)0.2475 (3)0.0504 (9)
H1A1.27530.48570.23120.060*
H1B1.39970.39170.18680.060*
C21.4901 (5)0.4715 (5)0.3212 (3)0.0552 (10)
H2A1.59290.43700.30430.066*
H2B1.49330.56660.31450.066*
C31.4699 (5)0.4379 (5)0.4265 (3)0.0543 (10)
C41.2979 (4)0.4246 (5)0.4560 (3)0.0538 (10)
C51.1889 (4)0.3489 (4)0.3773 (2)0.0426 (8)
C61.0297 (4)0.3354 (4)0.3850 (3)0.0471 (9)
C70.9206 (4)0.2529 (4)0.3168 (2)0.0444 (8)
C80.9996 (4)0.1674 (4)0.2466 (3)0.0414 (8)
C91.1337 (4)0.2540 (4)0.2070 (2)0.0402 (8)
H91.07820.33630.18710.048*
C101.2675 (4)0.2968 (4)0.2875 (2)0.0392 (7)
C111.1805 (4)0.1959 (5)0.1099 (2)0.0467 (8)
H11A1.20080.10220.11820.056*
H11B1.27920.23720.09230.056*
C121.0432 (4)0.2181 (5)0.0258 (3)0.0505 (9)
H12A1.05490.3052−0.00220.061*
H12B1.05380.1540−0.02620.061*
C130.8738 (4)0.2059 (4)0.0624 (3)0.0444 (8)
C140.8874 (4)0.1230 (4)0.1566 (3)0.0439 (8)
C150.7478 (5)0.0347 (5)0.1551 (3)0.0548 (10)
H150.70270.01050.21690.066*
C160.6376 (5)0.0597 (5)0.0623 (3)0.0610 (11)
H16A0.55000.11870.07520.073*
H16B0.5924−0.02190.03480.073*
C170.7501 (4)0.1237 (4)−0.0076 (3)0.0493 (9)
H170.81140.0522−0.03510.059*
C180.7977 (5)0.3403 (4)0.0818 (3)0.0520 (9)
H18A0.78870.39120.02180.078*
H18B0.86460.38640.13200.078*
H18C0.69210.32740.10360.078*
C191.3932 (4)0.1871 (4)0.3153 (3)0.0486 (9)
H19A1.33990.11240.34100.073*
H19B1.47390.21960.36460.073*
H19C1.44380.16130.25740.073*
C200.6656 (5)0.1966 (5)−0.0939 (3)0.0541 (9)
C210.5047 (5)0.2089 (7)−0.1179 (3)0.0687 (13)
H210.42570.1748−0.08080.082*
C220.7396 (6)0.2648 (5)−0.1704 (4)0.0666 (12)
H220.84990.2757−0.17470.080*
C230.6198 (7)0.3102 (5)−0.2348 (4)0.0716 (14)
H230.63480.3569−0.29230.086*
C281.2986 (5)0.3573 (8)0.5571 (3)0.0775 (16)
H28A1.36000.40950.60630.116*
H28B1.34670.27160.55410.116*
H28C1.18950.34870.57430.116*
C291.2402 (6)0.5703 (6)0.4622 (5)0.0755 (15)
H29A1.23700.61020.39790.113*
H29B1.31400.61810.50770.113*
H29C1.13410.57230.48490.113*
C301.0586 (5)0.0445 (4)0.3070 (3)0.0511 (9)
H30A1.1104−0.01530.26510.077*
H30B0.96780.00160.33220.077*
H30C1.13420.07090.36130.077*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0370 (14)0.101 (3)0.0708 (18)0.0006 (17)−0.0225 (13)−0.0111 (19)
O60.0343 (13)0.091 (2)0.0628 (16)−0.0005 (15)−0.0003 (11)−0.0290 (16)
O70.0232 (12)0.082 (2)0.0742 (17)−0.0001 (14)0.0049 (10)−0.0155 (16)
O150.0564 (17)0.0424 (14)0.0668 (17)−0.0008 (13)−0.0096 (13)−0.0048 (12)
O230.0601 (19)0.075 (2)0.085 (2)0.0165 (18)−0.0323 (16)−0.0062 (19)
C10.0315 (17)0.058 (2)0.060 (2)−0.0098 (17)−0.0086 (15)0.0033 (18)
C20.0330 (18)0.058 (2)0.071 (2)−0.0062 (18)−0.0121 (15)−0.002 (2)
C30.0367 (19)0.062 (2)0.061 (2)−0.0051 (18)−0.0128 (15)−0.0082 (19)
C40.0306 (18)0.072 (3)0.055 (2)0.0025 (19)−0.0158 (14)−0.0133 (19)
C50.0311 (16)0.0515 (19)0.0429 (16)0.0036 (16)−0.0091 (12)−0.0012 (15)
C60.0336 (16)0.061 (2)0.0448 (16)−0.0009 (17)−0.0049 (12)−0.0070 (16)
C70.0284 (16)0.056 (2)0.0479 (17)0.0004 (16)−0.0008 (12)0.0012 (16)
C80.0255 (14)0.0461 (19)0.0511 (17)−0.0025 (15)−0.0043 (12)−0.0021 (15)
C90.0243 (15)0.0468 (18)0.0481 (16)−0.0006 (15)−0.0044 (12)0.0013 (15)
C100.0260 (14)0.0438 (17)0.0461 (16)0.0030 (14)−0.0062 (12)0.0007 (14)
C110.0301 (15)0.061 (2)0.0483 (17)−0.0009 (17)−0.0027 (13)−0.0041 (17)
C120.0378 (18)0.064 (2)0.0475 (18)−0.0063 (18)−0.0073 (13)0.0010 (17)
C130.0336 (17)0.0467 (18)0.0504 (17)−0.0047 (15)−0.0093 (13)−0.0034 (16)
C140.0288 (16)0.0430 (19)0.058 (2)−0.0015 (15)−0.0051 (13)−0.0040 (16)
C150.0432 (19)0.059 (2)0.060 (2)−0.021 (2)−0.0044 (15)−0.0022 (19)
C160.046 (2)0.065 (3)0.069 (2)−0.014 (2)−0.0117 (17)−0.009 (2)
C170.0391 (19)0.051 (2)0.0547 (19)−0.0077 (17)−0.0134 (14)−0.0054 (17)
C180.0413 (19)0.0432 (19)0.067 (2)−0.0006 (17)−0.0164 (15)−0.0061 (18)
C190.0234 (15)0.056 (2)0.064 (2)0.0078 (16)−0.0068 (13)0.0006 (18)
C200.0399 (19)0.053 (2)0.065 (2)0.0002 (18)−0.0192 (16)−0.0077 (19)
C210.042 (2)0.091 (4)0.069 (2)0.010 (2)−0.0145 (17)−0.009 (3)
C220.056 (2)0.062 (3)0.076 (3)−0.009 (2)−0.025 (2)0.013 (2)
C230.074 (3)0.054 (2)0.079 (3)−0.007 (2)−0.035 (2)0.012 (2)
C280.047 (2)0.126 (5)0.056 (2)0.001 (3)−0.0131 (17)−0.003 (3)
C290.049 (2)0.075 (3)0.099 (3)−0.002 (2)−0.008 (2)−0.036 (3)
C300.0405 (18)0.050 (2)0.061 (2)−0.0072 (18)−0.0040 (15)0.0051 (18)
Geometric parameters (Å, °) top
O3—C31.230 (5)C12—H12A0.9700
O6—C61.369 (5)C12—H12B0.9700
O6—H60.8200C13—C141.525 (5)
O7—C71.223 (4)C13—C181.537 (6)
O15—C151.444 (6)C13—C171.572 (5)
O15—C141.465 (5)C14—C151.464 (5)
O23—C231.360 (7)C15—C161.507 (6)
O23—C211.370 (6)C15—H150.9800
C1—C101.538 (5)C16—C171.535 (6)
C1—C21.541 (5)C16—H16A0.9700
C1—H1A0.9700C16—H16B0.9700
C1—H1B0.9700C17—C201.502 (5)
C2—C31.491 (6)C17—H170.9800
C2—H2A0.9700C18—H18A0.9600
C2—H2B0.9700C18—H18B0.9600
C3—C41.524 (6)C18—H18C0.9600
C4—C281.531 (7)C19—H19A0.9600
C4—C51.538 (5)C19—H19B0.9600
C4—C291.559 (8)C19—H19C0.9600
C5—C61.343 (5)C20—C211.351 (6)
C5—C101.529 (5)C20—C221.433 (7)
C6—C71.491 (5)C21—H210.9300
C7—O71.223 (4)C22—C231.342 (6)
C7—C81.486 (5)C22—H220.9300
C8—C141.532 (5)C23—H230.9300
C8—C301.548 (5)C28—H28A0.9600
C8—C91.553 (5)C28—H28B0.9600
C9—C111.525 (5)C28—H28C0.9600
C9—C101.546 (4)C29—H29A0.9600
C9—H90.9800C29—H29B0.9600
C10—C191.548 (5)C29—H29C0.9600
C11—C121.552 (5)C30—H30A0.9600
C11—H11A0.9700C30—H30B0.9600
C11—H11B0.9700C30—H30C0.9600
C12—C131.539 (5)
C6—O6—H6109.5C12—C13—C17114.4 (3)
C15—O15—C1460.4 (3)C15—C14—O1559.1 (3)
C23—O23—C21106.2 (3)C15—C14—C13109.2 (3)
C10—C1—C2113.3 (3)O15—C14—C13110.5 (3)
C10—C1—H1A108.9C15—C14—C8127.9 (3)
C2—C1—H1A108.9O15—C14—C8113.8 (3)
C10—C1—H1B108.9C13—C14—C8119.8 (3)
C2—C1—H1B108.9O15—C15—C1460.5 (2)
H1A—C1—H1B107.7O15—C15—C16111.6 (3)
C3—C2—C1113.4 (3)C14—C15—C16109.1 (4)
C3—C2—H2A108.9O15—C15—H15120.4
C1—C2—H2A108.9C14—C15—H15120.4
C3—C2—H2B108.9C16—C15—H15120.4
C1—C2—H2B108.9C15—C16—C17103.3 (3)
H2A—C2—H2B107.7C15—C16—H16A111.1
O3—C3—C2121.6 (4)C17—C16—H16A111.1
O3—C3—C4120.7 (4)C15—C16—H16B111.1
C2—C3—C4117.6 (3)C17—C16—H16B111.1
C3—C4—C28110.4 (3)H16A—C16—H16B109.1
C3—C4—C5111.5 (3)C20—C17—C16115.0 (3)
C28—C4—C5110.5 (4)C20—C17—C13116.2 (3)
C3—C4—C29103.3 (4)C16—C17—C13104.6 (3)
C28—C4—C29110.5 (5)C20—C17—H17106.8
C5—C4—C29110.3 (3)C16—C17—H17106.8
C6—C5—C10121.5 (3)C13—C17—H17106.8
C6—C5—C4121.1 (3)C13—C18—H18A109.5
C10—C5—C4117.3 (3)C13—C18—H18B109.5
C5—C6—O6121.9 (3)H18A—C18—H18B109.5
C5—C6—C7123.7 (3)C13—C18—H18C109.5
O6—C6—C7114.3 (3)H18A—C18—H18C109.5
O7—C7—C8124.6 (3)H18B—C18—H18C109.5
O7—C7—C6118.5 (3)C10—C19—H19A109.5
C8—C7—C6116.6 (3)C10—C19—H19B109.5
C7—C8—C14114.2 (3)H19A—C19—H19B109.5
C7—C8—C30105.5 (3)C10—C19—H19C109.5
C14—C8—C30108.9 (3)H19A—C19—H19C109.5
C7—C8—C9105.3 (3)H19B—C19—H19C109.5
C14—C8—C9107.1 (3)C21—C20—C22105.1 (4)
C30—C8—C9115.9 (3)C21—C20—C17127.8 (4)
C11—C9—C10119.6 (3)C22—C20—C17127.0 (4)
C11—C9—C8109.1 (3)C20—C21—O23111.0 (5)
C10—C9—C8114.0 (3)C20—C21—H21124.5
C11—C9—H9104.1O23—C21—H21124.5
C10—C9—H9104.1C23—C22—C20107.2 (4)
C8—C9—H9104.1C23—C22—H22126.4
C5—C10—C1104.8 (3)C20—C22—H22126.4
C5—C10—C9109.1 (2)C22—C23—O23110.4 (5)
C1—C10—C9107.6 (3)C22—C23—H23124.8
C5—C10—C19112.5 (3)O23—C23—H23124.8
C1—C10—C19109.2 (3)C4—C28—H28A109.5
C9—C10—C19113.2 (3)C4—C28—H28B109.5
C9—C11—C12110.5 (3)H28A—C28—H28B109.5
C9—C11—H11A109.6C4—C28—H28C109.5
C12—C11—H11A109.6H28A—C28—H28C109.5
C9—C11—H11B109.6H28B—C28—H28C109.5
C12—C11—H11B109.6C4—C29—H29A109.5
H11A—C11—H11B108.1C4—C29—H29B109.5
C13—C12—C11112.4 (3)H29A—C29—H29B109.5
C13—C12—H12A109.1C4—C29—H29C109.5
C11—C12—H12A109.1H29A—C29—H29C109.5
C13—C12—H12B109.1H29B—C29—H29C109.5
C11—C12—H12B109.1C8—C30—H30A109.5
H12A—C12—H12B107.8C8—C30—H30B109.5
C14—C13—C18110.3 (3)H30A—C30—H30B109.5
C14—C13—C12108.4 (3)C8—C30—H30C109.5
C18—C13—C12112.7 (3)H30A—C30—H30C109.5
C14—C13—C17101.9 (3)H30B—C30—H30C109.5
C18—C13—C17108.6 (3)
C10—C1—C2—C3−23.4 (5)C9—C11—C12—C13−36.7 (5)
C1—C2—C3—O3152.0 (5)C11—C12—C13—C14−22.8 (5)
C1—C2—C3—C4−31.6 (6)C11—C12—C13—C1899.6 (4)
O3—C3—C4—C28−17.6 (7)C11—C12—C13—C17−135.7 (4)
C2—C3—C4—C28165.9 (5)C15—O15—C14—C13−100.7 (3)
O3—C3—C4—C5−141.0 (5)C15—O15—C14—C8121.2 (4)
C2—C3—C4—C542.5 (6)C18—C13—C14—C1596.1 (4)
O3—C3—C4—C29100.5 (5)C12—C13—C14—C15−140.0 (3)
C2—C3—C4—C29−76.0 (5)C17—C13—C14—C15−19.0 (4)
C3—C4—C5—C6−174.6 (4)C18—C13—C14—O15159.3 (3)
C28—C4—C5—C662.1 (5)C12—C13—C14—O15−76.8 (4)
C29—C4—C5—C6−60.4 (6)C17—C13—C14—O1544.2 (4)
C3—C4—C5—C102.0 (5)C18—C13—C14—C8−65.3 (4)
C28—C4—C5—C10−121.3 (4)C12—C13—C14—C858.5 (4)
C29—C4—C5—C10116.2 (4)C17—C13—C14—C8179.5 (3)
C10—C5—C6—O6−172.9 (4)C7—C8—C14—C15−67.0 (5)
C4—C5—C6—O63.6 (6)C30—C8—C14—C1550.7 (5)
C10—C5—C6—C79.5 (6)C9—C8—C14—C15176.8 (4)
C4—C5—C6—C7−174.0 (4)C7—C8—C14—O15−135.4 (4)
C5—C6—C7—O7−176.8 (4)C30—C8—C14—O15−17.7 (4)
O6—C6—C7—O75.5 (6)C9—C8—C14—O15108.4 (4)
C5—C6—C7—C89.0 (6)C7—C8—C14—C1390.6 (4)
O6—C6—C7—C8−168.8 (4)C30—C8—C14—C13−151.7 (3)
O7—C7—C8—C1426.4 (5)C9—C8—C14—C13−25.6 (4)
C6—C7—C8—C14−159.7 (3)C14—O15—C15—C16100.4 (4)
O7—C7—C8—C30−93.2 (4)C13—C14—C15—O15103.0 (3)
C6—C7—C8—C3080.7 (4)C8—C14—C15—O15−97.5 (4)
O7—C7—C8—C9143.6 (4)O15—C14—C15—C16−104.6 (4)
C6—C7—C8—C9−42.5 (4)C13—C14—C15—C16−1.6 (5)
C7—C8—C9—C11−159.9 (3)C8—C14—C15—C16157.9 (4)
C14—C8—C9—C11−37.9 (4)O15—C15—C16—C17−42.8 (5)
C30—C8—C9—C1183.8 (4)C14—C15—C16—C1722.2 (5)
C7—C8—C9—C1063.5 (4)C15—C16—C17—C20−162.2 (4)
C14—C8—C9—C10−174.6 (3)C15—C16—C17—C13−33.5 (5)
C30—C8—C9—C10−52.8 (4)C14—C13—C17—C20160.1 (3)
C6—C5—C10—C1124.8 (4)C18—C13—C17—C2043.8 (4)
C4—C5—C10—C1−51.8 (4)C12—C13—C17—C20−83.1 (5)
C6—C5—C10—C99.8 (5)C14—C13—C17—C1632.2 (4)
C4—C5—C10—C9−166.8 (3)C18—C13—C17—C16−84.1 (4)
C6—C5—C10—C19−116.7 (4)C12—C13—C17—C16149.0 (4)
C4—C5—C10—C1966.7 (4)C16—C17—C20—C21−1.9 (7)
C2—C1—C10—C563.1 (4)C13—C17—C20—C21−124.5 (5)
C2—C1—C10—C9179.2 (3)C16—C17—C20—C22−179.8 (4)
C2—C1—C10—C19−57.6 (4)C13—C17—C20—C2257.6 (6)
C11—C9—C10—C5−179.0 (3)C22—C20—C21—O230.8 (6)
C8—C9—C10—C5−47.3 (4)C17—C20—C21—O23−177.5 (4)
C11—C9—C10—C167.8 (4)C23—O23—C21—C20−0.1 (6)
C8—C9—C10—C1−160.4 (3)C21—C20—C22—C23−1.2 (6)
C11—C9—C10—C19−52.8 (4)C17—C20—C22—C23177.1 (4)
C8—C9—C10—C1978.9 (4)C20—C22—C23—O231.2 (6)
C10—C9—C11—C12−154.6 (3)C21—O23—C23—C22−0.7 (6)
C8—C9—C11—C1271.6 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O6—H6···O3i0.822.413.139 (4)149
C12—H12A···O15ii0.972.583.499 (5)159
C2—H2A···O7iii0.972.423.251 (6)144
O6—H6···O70.822.182.646 (4)116
Symmetry codes: (i) x−1, y, z; (ii) −x+2, y+1/2, −z; (iii) x+1, y, z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O6—H6···O3i0.822.413.139 (4)149
C12—H12A···O15ii0.972.583.499 (5)159
C2—H2A···O7iii0.972.423.251 (6)144
O6—H6···O70.822.182.646 (4)116
Symmetry codes: (i) x−1, y, z; (ii) −x+2, y+1/2, −z; (iii) x+1, y, z.
Acknowledgements top

SSD thanks the University of Madras for a University Research Fellowship.

references
References top

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.

Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, U.S.

Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.

Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands.

Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany

Hodges, R., McGeachin, S. G. & Raphael, R. A. (1963). J. Chem. Soc. pp. 2515–2526.

Narayanan, C. R., Dhaneshwar, N. N., Tavale, S. S. & Pant, L. M. (1980). Acta Cryst. B36, 486–489.

Nardelli, M. (1995). J. Appl. Cryst. 28, 659–?.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.

Zeumer, B., Zukerman-Schpector, I., Caracelli, I., Castro-Gamboa, I., Da Silva, M. F., das, G. F., Fernandes, J. B. & Vieira, P. C. (2000). Z. Kristallogr. New Cryst. Struct. 215, 143–145.