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The crystal structures of two intact limonoids, nimonol,7α-­acetyl-17α-(3-furyl)-6α-hydroxy-4α,4β,8β-trimethyl-5α,18α-androsta-1,14-dien-3-one (C28H36O5), and 6-oxonimonol,7α-acetyl-17α-(3-furyl)-4α,4β,8β-trimethyl-5α,18α-androsta-1,14-diene-3,6-dione (C28H34O5), are reported. The molecular features are mostly the same in the two structures; however the orientations of the acetoxy group are different in the two structures. The packing in nimonol is due to O—H...O hydrogen bonds while in 6-oxonimonol it is due to C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270199011609/bk1476sup1.cif
Contains datablocks I, II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270199011609/bk1476Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270199011609/bk1476IIsup3.hkl
Contains datablock den

CCDC references: 140957; 140958

Comment top

Neem leaves and neem oil have been used as ecofriendly insecticides in India for a long time and the constituents of neem like azadirachtins and a few other bioactive constituents have been studied for their biological activity (Govindachari, Narashiman et al., 1996). Recently the X-ray structures of a few azadirachtins and a few other compounds have been reported (Bilton et al., 1987; Kabaleeswaran et al., 1994; Govindachari, Geetha Gopalakrishnan et al., 1996). Nimonol, one of the limonoids, isolated from the leaves of neem (Suresh et al., 1997) exhibits antifeedant and ecdysis activity similar but to a lesser extent than the azadirachtins. The stereochemistry was clearly established by NMR techniques (Suresh et al., 1997). 6-Oxonimonol is a derivative of nimonol and was prepared to study the change of activity with the native compound. This paper reports the crystal structures of both nimonol, (I), and 6-oxonimonol, (II). However the absolute structure was not established by X-ray techniques.

The conformations of the B, C and D rings are chair, sofa and envelope, respectively, in both structures (Duax et al., 1975). However the ring A exists as a half-chair in nimonol and as a sofa in 6-oxonimonol. Consequently the torsion angles C1—C2—C3—O1, C2—C3—C4—C28 and C2—C3—C4—C29 are different in two structures. The furan ring E is pseudoaxially subsituted in both the structures with respect to the ring D. The orientation of the acetoxy group at C7, defined by the torsion angle C6—C7—O3—C26 is 109.1 (3)° (anticlinal) in nimonol and 70.4 (3)° (synclinal) in 6-oxonimonol. However, the orientations of the methyl carbons are close to one another. The ring pairs A/B and B/C are trans fused and C/D is quasi-trans fused in the two structures.

The geometric data pertinent to defining the hydrogen bonding scheme in nimonol,(I) are given in Table 2. However in 6-oxonimonol the molecular packing is due to C—H···O hydrogen bonds.

Experimental top

Crystals of nimonol (I) and 6-oxonimonol (II) were prepared from the methanol by slow evaporation.

Refinement top

The H atoms were placed at calculated positions and refined as riding using SHELXL97 (Sheldrick, 1997).

Computing details top

For both compounds, data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: SDP (Frenz, 1984); program(s) used to solve structure: SHELXS86 (Sheldrick, 1986); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. ORTEPII (Johnson, 1976) diagram of nimonol (I) at the 30% probability level.
[Figure 2] Fig. 2. ORTEPII (Johnson, 1976) diagram of 6-oxonimonol (II) at the 30% probability level.
(I) Nimonol top
Crystal data top
C28H36O5F(000) = 488
Mr = 452.57Dx = 1.195 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54180 Å
a = 10.087 (3) ÅCell parameters from 20 reflections
b = 11.044 (3) Åθ = 14–35°
c = 12.342 (3) ŵ = 0.65 mm1
β = 113.86 (2)°T = 293 K
V = 1257.3 (6) Å3Needle, colourless
Z = 20.30 × 0.20 × 0.10 mm
Data collection top
Enraf Nonius CAD-4
diffractometer
Rint = 0.038
Radiation source: fine-focus sealed tubeθmax = 72.0°, θmin = 3.9°
Graphite monochromatorh = 012
ω/2θ scansk = 013
3002 measured reflectionsl = 1513
2612 independent reflections3 standard reflections every 100 reflections
2443 reflections with I > 2σ(I) intensity decay: 3%
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)] = 0.062H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.194Calculated w = 1/[σ2(Fo2) + (0.1295P)2 + 0.1402P]
where P = (Fo2 + 2Fc2)/3
S = 1.15(Δ/σ)max = 0.001
2612 reflectionsΔρmax = 0.21 e Å3
298 parametersΔρmin = 0.22 e Å3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0022 (14)
Crystal data top
C28H36O5V = 1257.3 (6) Å3
Mr = 452.57Z = 2
Monoclinic, P21Cu Kα radiation
a = 10.087 (3) ŵ = 0.65 mm1
b = 11.044 (3) ÅT = 293 K
c = 12.342 (3) Å0.30 × 0.20 × 0.10 mm
β = 113.86 (2)°
Data collection top
Enraf Nonius CAD-4
diffractometer
Rint = 0.038
3002 measured reflections3 standard reflections every 100 reflections
2612 independent reflections intensity decay: 3%
2443 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0621 restraint
wR(F2) = 0.194H atoms treated by a mixture of independent and constrained refinement
S = 1.15Δρmax = 0.21 e Å3
2612 reflectionsΔρmin = 0.22 e Å3
298 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 > 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.

The two structures were solved by direct method by SHELXS86 (Sheldrick, 1986)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.0721 (6)0.6257 (5)0.3588 (4)0.1109 (15)
O20.2463 (3)0.2317 (3)0.5431 (2)0.0752 (8)
H20.19710.19600.57210.113*
O30.4098 (2)0.2294 (2)0.4128 (2)0.0555 (6)
O40.5396 (4)0.0891 (4)0.5454 (3)0.0873 (10)
O50.6962 (5)0.0809 (5)0.0689 (5)0.1110 (14)
C10.0816 (4)0.4812 (4)0.1878 (3)0.0628 (9)
H10.10600.49670.12410.075*
C20.0516 (4)0.5736 (4)0.2439 (4)0.0691 (9)
H2A0.05950.65260.22100.083*
C30.0069 (5)0.5519 (4)0.3404 (4)0.0705 (10)
C40.0595 (4)0.4390 (4)0.4172 (3)0.0618 (9)
C50.1441 (3)0.3549 (3)0.3642 (3)0.0528 (7)
H50.23940.39290.38690.063*
C60.1754 (4)0.2270 (4)0.4169 (3)0.0596 (8)
H60.08430.18200.39360.072*
C70.2776 (4)0.1595 (3)0.3736 (3)0.0560 (7)
H70.29830.07870.40930.067*
C80.2191 (4)0.1487 (3)0.2382 (3)0.0570 (8)
C90.1792 (4)0.2769 (3)0.1843 (3)0.0544 (7)
H90.27090.32160.21380.065*
C100.0767 (4)0.3522 (4)0.2257 (3)0.0555 (8)
C260.5303 (4)0.1860 (4)0.4999 (4)0.0651 (9)
C110.1306 (5)0.2720 (5)0.0487 (3)0.0711 (10)
H11A0.03970.22820.01450.085*
H11B0.11280.35400.01790.085*
C120.2376 (6)0.2133 (7)0.0093 (4)0.100 (2)
H12A0.27090.27400.03070.120*
H12B0.18680.15180.04880.120*
C130.3704 (4)0.1546 (3)0.1043 (3)0.0534 (7)
C140.3346 (5)0.0969 (4)0.2010 (3)0.0631 (9)
C150.4117 (9)0.0024 (5)0.2391 (6)0.117 (3)
H150.41040.04930.30130.140*
C160.5019 (9)0.0316 (6)0.1715 (6)0.114 (3)
H16A0.50030.11760.15490.136*
H16B0.60150.00540.21380.136*
C170.4252 (5)0.0416 (4)0.0582 (4)0.0657 (9)
H170.33940.00460.00790.079*
C180.4913 (6)0.2469 (5)0.1548 (6)0.0909 (16)
H18A0.51140.28160.09170.136*
H18B0.57690.20800.21030.136*
H18C0.46200.30970.19430.136*
C190.0840 (4)0.3112 (5)0.1690 (4)0.0774 (12)
H19A0.09120.22900.19140.116*
H19B0.11920.31650.08430.116*
H19C0.14090.36270.19610.116*
C200.5115 (5)0.0650 (4)0.0130 (4)0.0660 (9)
C210.6550 (6)0.0580 (6)0.0205 (5)0.0885 (14)
H210.71970.03940.09720.106*
C220.4568 (7)0.0955 (6)0.1370 (5)0.0915 (15)
H220.36050.10710.18870.110*
C230.5748 (11)0.1039 (7)0.1626 (7)0.117 (2)
H230.57120.12340.23700.140*
C270.6485 (5)0.2760 (6)0.5279 (5)0.0858 (13)
H27A0.61270.34630.47890.129*
H27B0.72690.24120.51320.129*
H27C0.68250.29890.60980.129*
C280.1637 (5)0.4903 (5)0.5381 (4)0.0771 (11)
H28A0.20280.42490.59320.116*
H28B0.11190.54480.56760.116*
H28C0.24140.53290.52870.116*
C290.0671 (5)0.3782 (6)0.4347 (5)0.0847 (13)
H29A0.03270.30740.48320.127*
H29B0.14010.35530.35910.127*
H29C0.10770.43370.47280.127*
C300.0917 (6)0.0560 (5)0.1977 (5)0.0808 (12)
H30A0.01640.08520.21970.121*
H30B0.12610.02060.23510.121*
H30C0.05400.04660.11320.121*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.137 (3)0.106 (3)0.109 (3)0.051 (3)0.069 (3)0.004 (2)
O20.0798 (17)0.092 (2)0.0579 (13)0.0025 (16)0.0320 (12)0.0106 (15)
O30.0491 (12)0.0567 (12)0.0556 (12)0.0007 (10)0.0159 (9)0.0058 (10)
O40.078 (2)0.091 (2)0.0832 (19)0.0158 (17)0.0226 (15)0.0309 (18)
O50.119 (3)0.120 (4)0.123 (3)0.002 (3)0.078 (3)0.011 (3)
C10.0562 (18)0.068 (2)0.0613 (18)0.0127 (16)0.0202 (15)0.0061 (17)
C20.070 (2)0.062 (2)0.076 (2)0.0118 (18)0.0304 (18)0.0053 (18)
C30.066 (2)0.073 (2)0.070 (2)0.0128 (19)0.0246 (17)0.0075 (19)
C40.0514 (17)0.072 (2)0.0655 (18)0.0027 (16)0.0271 (15)0.0065 (18)
C50.0418 (14)0.0620 (18)0.0538 (16)0.0048 (13)0.0186 (12)0.0003 (14)
C60.0567 (17)0.063 (2)0.0591 (17)0.0066 (16)0.0235 (14)0.0056 (15)
C70.0542 (17)0.0517 (17)0.0619 (17)0.0055 (14)0.0231 (14)0.0099 (15)
C80.0596 (18)0.0486 (16)0.0600 (17)0.0033 (15)0.0214 (14)0.0008 (14)
C90.0510 (16)0.0532 (16)0.0541 (16)0.0046 (14)0.0164 (13)0.0016 (14)
C100.0462 (16)0.0607 (19)0.0558 (16)0.0008 (14)0.0167 (13)0.0001 (15)
C260.055 (2)0.077 (2)0.0604 (17)0.0108 (17)0.0208 (15)0.0025 (18)
C110.069 (2)0.080 (3)0.0535 (17)0.020 (2)0.0135 (15)0.0003 (18)
C120.089 (3)0.150 (6)0.0541 (19)0.054 (4)0.023 (2)0.020 (3)
C130.0584 (18)0.0469 (15)0.0500 (15)0.0029 (14)0.0168 (13)0.0008 (13)
C140.080 (2)0.0485 (17)0.0640 (19)0.0044 (16)0.0326 (17)0.0007 (15)
C150.189 (7)0.078 (3)0.133 (5)0.062 (4)0.116 (5)0.049 (3)
C160.178 (7)0.079 (3)0.122 (4)0.066 (4)0.101 (5)0.042 (3)
C170.079 (2)0.0498 (17)0.071 (2)0.0031 (17)0.0325 (19)0.0090 (16)
C180.092 (3)0.073 (3)0.129 (4)0.025 (2)0.067 (3)0.047 (3)
C190.0480 (19)0.092 (3)0.082 (2)0.0003 (19)0.0152 (17)0.016 (2)
C200.082 (2)0.0535 (19)0.0665 (19)0.0034 (17)0.0336 (17)0.0104 (16)
C210.086 (3)0.099 (4)0.089 (3)0.003 (3)0.043 (2)0.016 (3)
C220.113 (4)0.089 (3)0.074 (2)0.018 (3)0.039 (3)0.004 (2)
C230.182 (8)0.091 (4)0.120 (5)0.013 (5)0.105 (6)0.005 (4)
C270.054 (2)0.091 (3)0.094 (3)0.000 (2)0.011 (2)0.016 (3)
C280.076 (3)0.086 (3)0.068 (2)0.004 (2)0.029 (2)0.017 (2)
C290.067 (2)0.102 (4)0.102 (3)0.005 (2)0.052 (2)0.007 (3)
C300.084 (3)0.063 (2)0.088 (3)0.018 (2)0.026 (2)0.016 (2)
Geometric parameters (Å, º) top
O1—C31.223 (5)C12—H12B0.9700
O2—C61.428 (4)C13—C141.520 (5)
O2—H20.8200C13—C181.516 (6)
O3—C261.344 (5)C13—C171.562 (5)
O3—C71.445 (4)C14—C151.316 (6)
O4—C261.195 (6)C15—C161.497 (7)
O5—C231.325 (10)C15—H150.9300
O5—C211.350 (6)C16—C171.527 (7)
C1—C21.334 (6)C16—H16A0.9700
C1—C101.506 (6)C16—H16B0.9700
C1—H10.9300C17—C201.487 (6)
C2—C31.455 (6)C17—H170.9800
C2—H2A0.9300C18—H18A0.9600
C3—C41.526 (6)C18—H18B0.9600
C4—C291.533 (5)C18—H18C0.9600
C4—C281.543 (6)C19—H19A0.9600
C4—C51.572 (5)C19—H19B0.9600
C5—C61.534 (5)C19—H19C0.9600
C5—C101.563 (5)C20—C211.338 (7)
C5—H50.9800C20—C221.442 (6)
C6—C71.533 (5)C21—H210.9300
C6—H60.9800C22—C231.353 (10)
C7—C81.534 (5)C22—H220.9300
C7—H70.9800C23—H230.9300
C8—C141.526 (5)C27—H27A0.9600
C8—C91.547 (5)C27—H27B0.9600
C8—C301.558 (5)C27—H27C0.9600
C9—C111.542 (5)C28—H28A0.9600
C9—C101.565 (5)C28—H28B0.9600
C9—H90.9800C28—H28C0.9600
C10—C191.551 (5)C29—H29A0.9600
C26—C271.482 (7)C29—H29B0.9600
C11—C121.499 (6)C29—H29C0.9600
C11—H11A0.9700C30—H30A0.9600
C11—H11B0.9700C30—H30B0.9600
C12—C131.523 (5)C30—H30C0.9600
C12—H12A0.9700
C6—O2—H2109.5C18—C13—C12109.9 (5)
C26—O3—C7119.4 (3)C14—C13—C17100.5 (3)
C23—O5—C21105.5 (5)C18—C13—C17110.0 (3)
C2—C1—C10121.3 (4)C12—C13—C17113.0 (3)
C2—C1—H1119.3C15—C14—C13109.7 (4)
C10—C1—H1119.3C15—C14—C8128.1 (4)
C1—C2—C3120.6 (4)C13—C14—C8122.1 (3)
C1—C2—H2A119.7C14—C15—C16112.6 (4)
C3—C2—H2A119.7C14—C15—H15123.7
O1—C3—C2118.9 (4)C16—C15—H15123.7
O1—C3—C4121.2 (4)C15—C16—C17101.5 (4)
C2—C3—C4119.9 (3)C15—C16—H16A111.5
C3—C4—C29110.2 (4)C17—C16—H16A111.5
C3—C4—C28103.4 (4)C15—C16—H16B111.5
C29—C4—C28107.8 (4)C17—C16—H16B111.5
C3—C4—C5109.6 (3)H16A—C16—H16B109.3
C29—C4—C5115.0 (4)C20—C17—C16115.6 (4)
C28—C4—C5110.3 (3)C20—C17—C13117.0 (3)
C6—C5—C10111.8 (3)C16—C17—C13102.2 (3)
C6—C5—C4114.9 (3)C20—C17—H17107.1
C10—C5—C4113.4 (3)C16—C17—H17107.1
C6—C5—H5105.2C13—C17—H17107.1
C10—C5—H5105.2C13—C18—H18A109.5
C4—C5—H5105.2C13—C18—H18B109.5
O2—C6—C5110.9 (3)H18A—C18—H18B109.5
O2—C6—C7106.7 (3)C13—C18—H18C109.5
C5—C6—C7110.6 (3)H18A—C18—H18C109.5
O2—C6—H6109.5H18B—C18—H18C109.5
C5—C6—H6109.5C10—C19—H19A109.5
C7—C6—H6109.5C10—C19—H19B109.5
O3—C7—C8107.6 (3)H19A—C19—H19B109.5
O3—C7—C6106.5 (3)C10—C19—H19C109.5
C8—C7—C6113.6 (3)H19A—C19—H19C109.5
O3—C7—H7109.7H19B—C19—H19C109.5
C8—C7—H7109.7C21—C20—C22104.0 (4)
C6—C7—H7109.7C21—C20—C17128.8 (4)
C14—C8—C7110.6 (3)C22—C20—C17127.1 (4)
C14—C8—C9108.1 (3)C20—C21—O5112.9 (5)
C7—C8—C9108.4 (3)C20—C21—H21123.5
C14—C8—C30106.8 (3)O5—C21—H21123.5
C7—C8—C30107.8 (3)C23—C22—C20105.6 (6)
C9—C8—C30115.2 (3)C23—C22—H22127.2
C11—C9—C8110.4 (3)C20—C22—H22127.2
C11—C9—C10114.3 (3)O5—C23—C22111.9 (5)
C8—C9—C10115.9 (3)O5—C23—H23124.0
C11—C9—H9105.0C22—C23—H23124.0
C8—C9—H9105.0C26—C27—H27A109.5
C10—C9—H9105.0C26—C27—H27B109.5
C1—C10—C19107.2 (3)H27A—C27—H27B109.5
C1—C10—C5105.5 (3)C26—C27—H27C109.5
C19—C10—C5114.3 (3)H27A—C27—H27C109.5
C1—C10—C9107.0 (3)H27B—C27—H27C109.5
C19—C10—C9113.9 (3)C4—C28—H28A109.5
C5—C10—C9108.4 (3)C4—C28—H28B109.5
O4—C26—O3124.7 (4)H28A—C28—H28B109.5
O4—C26—C27126.1 (4)C4—C28—H28C109.5
O3—C26—C27109.2 (4)H28A—C28—H28C109.5
C12—C11—C9114.4 (3)H28B—C28—H28C109.5
C12—C11—H11A108.7C4—C29—H29A109.5
C9—C11—H11A108.7C4—C29—H29B109.5
C12—C11—H11B108.7H29A—C29—H29B109.5
C9—C11—H11B108.7C4—C29—H29C109.5
H11A—C11—H11B107.6H29A—C29—H29C109.5
C11—C12—C13117.3 (3)H29B—C29—H29C109.5
C11—C12—H12A108.0C8—C30—H30A109.5
C13—C12—H12A108.0C8—C30—H30B109.5
C11—C12—H12B108.0H30A—C30—H30B109.5
C13—C12—H12B108.0C8—C30—H30C109.5
H12A—C12—H12B107.2H30A—C30—H30C109.5
C14—C13—C18111.5 (4)H30B—C30—H30C109.5
C14—C13—C12111.6 (4)
C10—C1—C2—C32.8 (6)C8—C9—C10—C1166.4 (3)
C1—C2—C3—O1151.2 (5)C11—C9—C10—C1954.7 (5)
C1—C2—C3—C429.2 (6)C8—C9—C10—C1975.4 (4)
O1—C3—C4—C2946.3 (6)C11—C9—C10—C5176.9 (3)
C2—C3—C4—C29134.2 (4)C8—C9—C10—C553.0 (4)
O1—C3—C4—C2868.7 (5)C7—O3—C26—O43.7 (6)
C2—C3—C4—C28110.9 (4)C7—O3—C26—C27177.3 (3)
O1—C3—C4—C5173.8 (4)C8—C9—C11—C1254.5 (6)
C2—C3—C4—C56.7 (5)C10—C9—C11—C12172.8 (5)
C3—C4—C5—C6167.8 (3)C9—C11—C12—C136.4 (8)
C29—C4—C5—C643.1 (4)C11—C12—C13—C1435.4 (7)
C28—C4—C5—C679.0 (4)C11—C12—C13—C1888.9 (7)
C3—C4—C5—C1037.6 (4)C11—C12—C13—C17147.8 (5)
C29—C4—C5—C1087.2 (4)C18—C13—C14—C1591.9 (6)
C28—C4—C5—C10150.7 (3)C12—C13—C14—C15144.7 (6)
C10—C5—C6—O2175.8 (3)C17—C13—C14—C1524.7 (6)
C4—C5—C6—O253.1 (4)C18—C13—C14—C891.0 (5)
C10—C5—C6—C757.7 (4)C12—C13—C14—C832.3 (6)
C4—C5—C6—C7171.3 (3)C17—C13—C14—C8152.4 (3)
C26—O3—C7—C8128.7 (3)C7—C8—C14—C1552.0 (7)
C26—O3—C7—C6109.1 (3)C9—C8—C14—C15170.6 (6)
O2—C6—C7—O360.4 (4)C30—C8—C14—C1565.0 (7)
C5—C6—C7—O360.2 (3)C7—C8—C14—C13131.5 (4)
O2—C6—C7—C8178.7 (3)C9—C8—C14—C1313.0 (5)
C5—C6—C7—C858.1 (4)C30—C8—C14—C13111.5 (4)
O3—C7—C8—C1454.3 (4)C13—C14—C15—C163.6 (8)
C6—C7—C8—C14172.0 (3)C8—C14—C15—C16173.2 (5)
O3—C7—C8—C964.0 (4)C14—C15—C16—C1719.6 (9)
C6—C7—C8—C953.6 (4)C15—C16—C17—C20161.4 (5)
O3—C7—C8—C30170.7 (3)C15—C16—C17—C1333.2 (6)
C6—C7—C8—C3071.6 (4)C14—C13—C17—C20162.4 (4)
C14—C8—C9—C1155.8 (4)C18—C13—C17—C2044.7 (5)
C7—C8—C9—C11175.7 (3)C12—C13—C17—C2078.5 (5)
C30—C8—C9—C1163.5 (4)C14—C13—C17—C1635.0 (5)
C14—C8—C9—C10172.3 (3)C18—C13—C17—C1682.6 (5)
C7—C8—C9—C1052.4 (4)C12—C13—C17—C16154.1 (5)
C30—C8—C9—C1068.4 (4)C16—C17—C20—C2118.2 (7)
C2—C1—C10—C1982.2 (5)C13—C17—C20—C21102.3 (6)
C2—C1—C10—C540.0 (5)C16—C17—C20—C22158.7 (5)
C2—C1—C10—C9155.3 (4)C13—C17—C20—C2280.8 (6)
C6—C5—C10—C1168.4 (3)C22—C20—C21—O50.1 (7)
C4—C5—C10—C159.8 (4)C17—C20—C21—O5177.5 (5)
C6—C5—C10—C1974.1 (4)C23—O5—C21—C200.3 (7)
C4—C5—C10—C1957.7 (4)C21—C20—C22—C230.4 (7)
C6—C5—C10—C954.1 (4)C17—C20—C22—C23177.9 (5)
C4—C5—C10—C9174.1 (3)C21—O5—C23—C220.6 (8)
C11—C9—C10—C163.6 (4)C20—C22—C23—O50.6 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AH···AD···AD—H···A
O2—H2···O1i1.95 (1)2.768 (6)175 (4)
C1—H1···O5ii2.56 (6)3.325 (7)130 (4)
C23—H23···O4iii2.48 (8)3.472 (9)153 (5)
Symmetry codes: (i) x, y1/2, z+1; (ii) x+1, y+1/2, z; (iii) x, y, z1.
(II) 6-oxonimonol top
Crystal data top
C28H34O5Dx = 1.243 Mg m3
Mr = 450.55Cu Kα radiation, λ = 1.54180 Å
Orthorhombic, P212121Cell parameters from 25 reflections
a = 10.805 (1) Åθ = 12–36°
b = 12.710 (2) ŵ = 0.67 mm1
c = 17.538 (2) ÅT = 293 K
V = 2408.5 (5) Å3Needle, colourless
Z = 40.30 × 0.25 × 0.15 mm
F(000) = 968
Data collection top
Enraf Nonius CAD-4
diffractometer
Rint = 0.000
Radiation source: fine-focus sealed tubeθmax = 67.9°, θmin = 4.3°
Graphite monochromatorh = 012
ω/2θ scansk = 015
2481 measured reflectionsl = 021
2481 independent reflections3 standard reflections every 100 reflections
2222 reflections with I > 2σ(I) intensity decay: 3%
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)] = 0.043H-atom parameters constrained
wR(F2) = 0.129Calculated w = 1/[σ2(Fo2) + (0.1007P)2 + 1.2632P]
where P = (Fo2 + 2Fc2)/3
S = 0.80(Δ/σ)max = 0.001
2481 reflectionsΔρmax = 0.22 e Å3
298 parametersΔρmin = 0.23 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0053 (5)
Crystal data top
C28H34O5V = 2408.5 (5) Å3
Mr = 450.55Z = 4
Orthorhombic, P212121Cu Kα radiation
a = 10.805 (1) ŵ = 0.67 mm1
b = 12.710 (2) ÅT = 293 K
c = 17.538 (2) Å0.30 × 0.25 × 0.15 mm
Data collection top
Enraf Nonius CAD-4
diffractometer
Rint = 0.000
2481 measured reflections3 standard reflections every 100 reflections
2481 independent reflections intensity decay: 3%
2222 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.129H-atom parameters constrained
S = 0.80Δρmax = 0.22 e Å3
2481 reflectionsΔρmin = 0.23 e Å3
298 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 > 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
O10.0612 (2)0.2036 (2)0.23388 (16)0.0726 (7)
O20.4187 (2)0.17737 (18)0.15882 (16)0.0673 (7)
O30.34749 (19)0.36430 (15)0.02342 (10)0.0436 (5)
O40.3623 (6)0.2081 (2)0.02861 (19)0.141 (2)
O50.5029 (3)0.9223 (2)0.08528 (19)0.0876 (9)
C10.1231 (3)0.4331 (2)0.22804 (18)0.0505 (7)
H10.11090.50490.23510.061*
C20.0259 (3)0.3710 (3)0.2306 (2)0.0600 (9)
H20.05110.40170.23880.072*
C30.0311 (3)0.2561 (3)0.22131 (19)0.0534 (7)
C40.1529 (3)0.2049 (2)0.19915 (18)0.0497 (7)
C50.2388 (3)0.2909 (2)0.16667 (16)0.0405 (6)
H50.19630.31410.12020.049*
C60.3647 (3)0.2557 (2)0.13848 (17)0.0441 (7)
C70.4270 (3)0.3347 (2)0.08616 (16)0.0410 (6)
H70.50510.30610.06680.049*
C80.4510 (2)0.4368 (2)0.13144 (15)0.0378 (6)
C90.3255 (2)0.47593 (19)0.16407 (14)0.0360 (6)
H90.27280.48710.11930.043*
C100.2534 (3)0.3945 (2)0.21429 (16)0.0410 (6)
C110.3420 (3)0.5855 (2)0.19918 (16)0.0469 (7)
H11A0.26550.60630.22380.056*
H11B0.40590.58240.23790.056*
C120.3767 (4)0.6673 (2)0.1409 (2)0.0620 (9)
H12A0.43130.71790.16510.074*
H12B0.30220.70460.12610.074*
C130.4401 (2)0.6274 (2)0.06832 (15)0.0376 (6)
C140.5031 (2)0.5217 (2)0.07965 (15)0.0377 (6)
C150.6087 (3)0.5176 (3)0.0411 (2)0.0525 (8)
H150.66040.45910.03990.063*
C160.6348 (3)0.6182 (3)0.0002 (2)0.0592 (9)
H16A0.61170.61350.05350.071*
H16B0.72150.63750.00360.071*
C170.5529 (3)0.6954 (2)0.04252 (17)0.0425 (6)
H170.59780.71390.08920.051*
C180.3466 (3)0.6196 (2)0.0019 (2)0.0532 (8)
H18A0.30680.68650.00520.080*
H18B0.28550.56720.01350.080*
H18C0.38940.60040.04400.080*
C190.3130 (4)0.3800 (3)0.29406 (16)0.0574 (8)
H19A0.39640.35530.28830.086*
H19B0.26600.32970.32280.086*
H19C0.31340.44620.32040.086*
C200.5235 (3)0.7975 (2)0.00354 (18)0.0480 (7)
C210.5328 (4)0.8195 (3)0.0705 (2)0.0677 (10)
H210.55650.77120.10760.081*
C220.4864 (3)0.8930 (2)0.0391 (2)0.0617 (9)
H220.47220.90360.09080.074*
C230.4758 (4)0.9653 (3)0.0172 (3)0.0798 (13)
H230.45291.03510.00990.096*
C260.3239 (4)0.2940 (2)0.03131 (18)0.0594 (9)
C270.2445 (4)0.3391 (3)0.09219 (19)0.0701 (10)
H27A0.22560.41110.08020.105*
H27B0.16900.29950.09560.105*
H27C0.28740.33600.14010.105*
C280.2003 (4)0.1468 (3)0.2706 (2)0.0740 (11)
H28A0.27770.11310.25920.111*
H28B0.14090.09470.28580.111*
H28C0.21190.19630.31130.111*
C290.1278 (4)0.1233 (3)0.1361 (2)0.0761 (11)
H29A0.20420.09040.12150.114*
H29B0.09210.15780.09270.114*
H29C0.07160.07090.15480.114*
C300.5509 (3)0.4112 (3)0.19176 (19)0.0539 (8)
H30A0.52070.35750.22550.081*
H30B0.56960.47340.22060.081*
H30C0.62450.38680.16670.081*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0585 (14)0.0664 (15)0.0930 (18)0.0181 (13)0.0096 (14)0.0088 (15)
O20.0669 (15)0.0444 (12)0.0906 (17)0.0179 (11)0.0097 (14)0.0199 (12)
O30.0501 (11)0.0381 (9)0.0428 (10)0.0024 (9)0.0030 (9)0.0088 (8)
O40.282 (6)0.0472 (15)0.093 (2)0.044 (3)0.067 (3)0.0243 (15)
O50.099 (2)0.0670 (16)0.096 (2)0.0132 (17)0.0195 (19)0.0406 (17)
C10.0545 (17)0.0393 (14)0.0577 (17)0.0061 (13)0.0163 (15)0.0046 (14)
C20.0516 (18)0.0536 (17)0.075 (2)0.0080 (15)0.0157 (17)0.0122 (17)
C30.0527 (17)0.0537 (17)0.0538 (17)0.0072 (15)0.0032 (15)0.0093 (15)
C40.0531 (17)0.0390 (14)0.0571 (17)0.0034 (14)0.0013 (15)0.0066 (13)
C50.0445 (14)0.0333 (13)0.0438 (14)0.0001 (12)0.0000 (12)0.0036 (11)
C60.0485 (16)0.0303 (13)0.0536 (16)0.0058 (12)0.0011 (14)0.0001 (12)
C70.0395 (14)0.0326 (13)0.0509 (15)0.0061 (11)0.0015 (12)0.0036 (12)
C80.0381 (13)0.0316 (12)0.0438 (14)0.0025 (11)0.0030 (12)0.0001 (11)
C90.0405 (14)0.0325 (12)0.0350 (12)0.0029 (11)0.0012 (11)0.0009 (10)
C100.0496 (16)0.0328 (13)0.0406 (13)0.0003 (12)0.0027 (12)0.0010 (11)
C110.0588 (18)0.0379 (13)0.0441 (14)0.0038 (14)0.0058 (14)0.0091 (12)
C120.083 (2)0.0341 (14)0.069 (2)0.0005 (16)0.027 (2)0.0068 (14)
C130.0369 (13)0.0308 (12)0.0452 (14)0.0003 (11)0.0026 (12)0.0001 (12)
C140.0367 (13)0.0329 (12)0.0437 (13)0.0001 (11)0.0029 (12)0.0024 (11)
C150.0430 (15)0.0436 (15)0.071 (2)0.0085 (13)0.0088 (15)0.0029 (15)
C160.0450 (16)0.0522 (18)0.081 (2)0.0008 (15)0.0184 (16)0.0078 (17)
C170.0389 (13)0.0382 (14)0.0504 (15)0.0056 (12)0.0050 (12)0.0011 (12)
C180.0424 (15)0.0462 (16)0.071 (2)0.0066 (14)0.0140 (15)0.0144 (16)
C190.077 (2)0.0567 (18)0.0388 (14)0.0006 (18)0.0024 (15)0.0060 (14)
C200.0415 (14)0.0410 (14)0.0614 (17)0.0085 (13)0.0050 (14)0.0084 (14)
C210.075 (2)0.061 (2)0.067 (2)0.0126 (19)0.0063 (19)0.0193 (18)
C220.061 (2)0.0445 (16)0.080 (2)0.0004 (16)0.0152 (19)0.0059 (16)
C230.069 (2)0.0470 (18)0.123 (4)0.0054 (18)0.025 (3)0.026 (2)
C260.093 (3)0.0364 (15)0.0493 (17)0.0075 (17)0.0017 (18)0.0077 (13)
C270.087 (3)0.071 (2)0.0524 (18)0.021 (2)0.0131 (19)0.0044 (17)
C280.076 (2)0.059 (2)0.087 (3)0.0012 (19)0.004 (2)0.036 (2)
C290.088 (3)0.0493 (19)0.091 (3)0.022 (2)0.017 (2)0.0111 (19)
C300.0507 (17)0.0526 (17)0.0586 (18)0.0042 (15)0.0113 (15)0.0078 (16)
Geometric parameters (Å, º) top
O1—C31.220 (4)C13—C181.545 (4)
O2—C61.208 (3)C13—C171.561 (4)
O3—C261.336 (3)C14—C151.328 (4)
O3—C71.446 (3)C15—C161.496 (4)
O4—C261.170 (4)C15—H150.9300
O5—C231.345 (6)C16—C171.520 (4)
O5—C211.371 (5)C16—H16A0.9700
C1—C21.314 (5)C16—H16B0.9700
C1—C101.511 (4)C17—C201.500 (4)
C1—H10.9300C17—H170.9800
C2—C31.470 (5)C18—H18A0.9600
C2—H20.9300C18—H18B0.9600
C3—C41.520 (5)C18—H18C0.9600
C4—C291.540 (5)C19—H19A0.9600
C4—C51.543 (4)C19—H19B0.9600
C4—C281.542 (5)C19—H19C0.9600
C5—C61.515 (4)C20—C211.333 (5)
C5—C101.567 (4)C20—C221.422 (5)
C5—H50.9800C21—H210.9300
C6—C71.518 (4)C22—C231.355 (5)
C7—C81.542 (4)C22—H220.9300
C7—H70.9800C23—H230.9300
C8—C141.519 (4)C26—C271.485 (5)
C8—C301.546 (4)C27—H27A0.9600
C8—C91.554 (4)C27—H27B0.9600
C9—C111.533 (3)C27—H27C0.9600
C9—C101.567 (4)C28—H28A0.9600
C9—H90.9800C28—H28B0.9600
C10—C191.551 (4)C28—H28C0.9600
C11—C121.506 (4)C29—H29A0.9600
C11—H11A0.9700C29—H29B0.9600
C11—H11B0.9700C29—H29C0.9600
C12—C131.531 (4)C30—H30A0.9600
C12—H12A0.9700C30—H30B0.9600
C12—H12B0.9700C30—H30C0.9600
C13—C141.519 (4)
C26—O3—C7119.1 (2)C15—C14—C13110.7 (2)
C23—O5—C21105.8 (3)C8—C14—C13122.7 (2)
C2—C1—C10123.7 (3)C14—C15—C16112.0 (3)
C2—C1—H1118.2C14—C15—H15124.0
C10—C1—H1118.2C16—C15—H15124.0
C1—C2—C3124.2 (3)C15—C16—C17101.7 (2)
C1—C2—H2117.9C15—C16—H16A111.4
C3—C2—H2117.9C17—C16—H16A111.4
O1—C3—C2119.5 (3)C15—C16—H16B111.4
O1—C3—C4121.3 (3)C17—C16—H16B111.4
C2—C3—C4119.1 (3)H16A—C16—H16B109.3
C3—C4—C29108.6 (3)C20—C17—C16117.2 (3)
C3—C4—C5108.1 (2)C20—C17—C13116.5 (2)
C29—C4—C5108.5 (3)C16—C17—C13103.9 (2)
C3—C4—C28106.6 (3)C20—C17—H17106.1
C29—C4—C28108.6 (3)C16—C17—H17106.1
C5—C4—C28116.1 (3)C13—C17—H17106.1
C6—C5—C4116.8 (2)C13—C18—H18A109.5
C6—C5—C10109.3 (2)C13—C18—H18B109.5
C4—C5—C10117.3 (2)H18A—C18—H18B109.5
C6—C5—H5103.8C13—C18—H18C109.5
C4—C5—H5103.8H18A—C18—H18C109.5
C10—C5—H5103.8H18B—C18—H18C109.5
O2—C6—C5125.5 (3)C10—C19—H19A109.5
O2—C6—C7120.7 (3)C10—C19—H19B109.5
C5—C6—C7113.6 (2)H19A—C19—H19B109.5
O3—C7—C6111.6 (2)C10—C19—H19C109.5
O3—C7—C8105.9 (2)H19A—C19—H19C109.5
C6—C7—C8108.6 (2)H19B—C19—H19C109.5
O3—C7—H7110.2C21—C20—C22105.6 (3)
C6—C7—H7110.2C21—C20—C17127.6 (3)
C8—C7—H7110.2C22—C20—C17126.7 (3)
C14—C8—C7110.6 (2)C20—C21—O5111.5 (4)
C14—C8—C30107.5 (2)C20—C21—H21124.3
C7—C8—C30107.0 (2)O5—C21—H21124.3
C14—C8—C9108.4 (2)C23—C22—C20106.5 (4)
C7—C8—C9108.2 (2)C23—C22—H22126.8
C30—C8—C9115.1 (2)C20—C22—H22126.8
C11—C9—C8109.7 (2)O5—C23—C22110.6 (4)
C11—C9—C10115.6 (2)O5—C23—H23124.7
C8—C9—C10115.4 (2)C22—C23—H23124.7
C11—C9—H9104.9O4—C26—O3121.9 (4)
C8—C9—H9104.9O4—C26—C27126.5 (3)
C10—C9—H9104.9O3—C26—C27111.6 (3)
C1—C10—C19106.3 (2)C26—C27—H27A109.5
C1—C10—C9109.8 (2)C26—C27—H27B109.5
C19—C10—C9112.3 (2)H27A—C27—H27B109.5
C1—C10—C5105.3 (2)C26—C27—H27C109.5
C19—C10—C5115.1 (2)H27A—C27—H27C109.5
C9—C10—C5107.8 (2)H27B—C27—H27C109.5
C12—C11—C9112.5 (2)C4—C28—H28A109.5
C12—C11—H11A109.1C4—C28—H28B109.5
C9—C11—H11A109.1H28A—C28—H28B109.5
C12—C11—H11B109.1C4—C28—H28C109.5
C9—C11—H11B109.1H28A—C28—H28C109.5
H11A—C11—H11B107.8H28B—C28—H28C109.5
C11—C12—C13116.5 (2)C4—C29—H29A109.5
C11—C12—H12A108.2C4—C29—H29B109.5
C13—C12—H12A108.2H29A—C29—H29B109.5
C11—C12—H12B108.2C4—C29—H29C109.5
C13—C12—H12B108.2H29A—C29—H29C109.5
H12A—C12—H12B107.3H29B—C29—H29C109.5
C14—C13—C12112.6 (2)C8—C30—H30A109.5
C14—C13—C18109.6 (2)C8—C30—H30B109.5
C12—C13—C18110.8 (3)H30A—C30—H30B109.5
C14—C13—C17100.3 (2)C8—C30—H30C109.5
C12—C13—C17114.0 (2)H30A—C30—H30C109.5
C18—C13—C17109.1 (2)H30B—C30—H30C109.5
C15—C14—C8126.5 (3)
C10—C1—C2—C30.7 (6)C4—C5—C10—C153.5 (3)
C1—C2—C3—O1171.0 (4)C6—C5—C10—C1972.7 (3)
C1—C2—C3—C46.7 (6)C4—C5—C10—C1963.3 (3)
O1—C3—C4—C2947.3 (4)C6—C5—C10—C953.4 (3)
C2—C3—C4—C29135.1 (3)C4—C5—C10—C9170.6 (2)
O1—C3—C4—C5164.9 (3)C8—C9—C11—C1264.4 (3)
C2—C3—C4—C517.4 (4)C10—C9—C11—C12163.0 (3)
O1—C3—C4—C2869.6 (4)C9—C11—C12—C1324.2 (5)
C2—C3—C4—C28108.0 (4)C11—C12—C13—C1423.1 (4)
C3—C4—C5—C6178.1 (2)C11—C12—C13—C18100.1 (4)
C29—C4—C5—C660.4 (3)C11—C12—C13—C17136.4 (3)
C28—C4—C5—C662.3 (4)C7—C8—C14—C1561.4 (4)
C3—C4—C5—C1049.2 (3)C30—C8—C14—C1555.1 (4)
C29—C4—C5—C10166.9 (3)C9—C8—C14—C15179.9 (3)
C28—C4—C5—C1070.5 (4)C7—C8—C14—C13121.4 (3)
C4—C5—C6—O223.8 (4)C30—C8—C14—C13122.1 (3)
C10—C5—C6—O2112.5 (3)C9—C8—C14—C133.0 (3)
C4—C5—C6—C7162.1 (2)C12—C13—C14—C15142.4 (3)
C10—C5—C6—C761.6 (3)C18—C13—C14—C1593.7 (3)
C26—O3—C7—C670.4 (3)C17—C13—C14—C1520.9 (3)
C26—O3—C7—C8171.5 (3)C12—C13—C14—C835.1 (4)
O2—C6—C7—O3132.3 (3)C18—C13—C14—C888.7 (3)
C5—C6—C7—O353.3 (3)C17—C13—C14—C8156.6 (2)
O2—C6—C7—C8111.4 (3)C8—C14—C15—C16176.3 (3)
C5—C6—C7—C863.1 (3)C13—C14—C15—C161.1 (4)
O3—C7—C8—C1455.0 (3)C14—C15—C16—C1719.8 (4)
C6—C7—C8—C14175.1 (2)C15—C16—C17—C20161.6 (3)
O3—C7—C8—C30171.8 (2)C15—C16—C17—C1331.6 (3)
C6—C7—C8—C3068.2 (3)C14—C13—C17—C20162.4 (3)
O3—C7—C8—C963.6 (3)C12—C13—C17—C2077.0 (3)
C6—C7—C8—C956.5 (3)C18—C13—C17—C2047.4 (3)
C14—C8—C9—C1151.6 (3)C14—C13—C17—C1631.9 (3)
C7—C8—C9—C11171.6 (2)C12—C13—C17—C16152.5 (3)
C30—C8—C9—C1168.8 (3)C18—C13—C17—C1683.1 (3)
C14—C8—C9—C10175.7 (2)C16—C17—C20—C2118.7 (5)
C7—C8—C9—C1055.7 (3)C13—C17—C20—C21105.2 (4)
C30—C8—C9—C1064.0 (3)C16—C17—C20—C22157.4 (3)
C2—C1—C10—C1995.3 (4)C13—C17—C20—C2278.7 (4)
C2—C1—C10—C9143.0 (3)C22—C20—C21—O50.6 (4)
C2—C1—C10—C527.2 (4)C17—C20—C21—O5177.5 (3)
C11—C9—C10—C162.1 (3)C23—O5—C21—C200.8 (5)
C8—C9—C10—C1168.0 (2)C21—C20—C22—C230.2 (4)
C11—C9—C10—C1955.9 (3)C17—C20—C22—C23177.1 (3)
C8—C9—C10—C1974.0 (3)C21—O5—C23—C220.6 (5)
C11—C9—C10—C5176.3 (2)C20—C22—C23—O50.2 (4)
C8—C9—C10—C553.8 (3)C7—O3—C26—O42.7 (6)
C6—C5—C10—C1170.5 (2)C7—O3—C26—C27178.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C27—H27C···O1i0.96 (1)2.37 (1)3.298 (5)161 (1)
C23—H23···O4ii0.93 (1)2.43 (1)3.226 (5)162 (1)
C11—H11A···O1iii0.97 (1)2.64 (1)3.583 (4)165 (1)
C1—H1···O1iii0.93 (1)2.64 (1)3.565 (4)174 (1)
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x, y+1, z; (iii) x, y+1/2, z+1/2.

Experimental details

(I)(II)
Crystal data
Chemical formulaC28H36O5C28H34O5
Mr452.57450.55
Crystal system, space groupMonoclinic, P21Orthorhombic, P212121
Temperature (K)293293
a, b, c (Å)10.087 (3), 11.044 (3), 12.342 (3)10.805 (1), 12.710 (2), 17.538 (2)
α, β, γ (°)90.00 (2), 113.86 (2), 90.00 (2)90.00 (1), 90.00 (1), 90.00 (1)
V3)1257.3 (6)2408.5 (5)
Z24
Radiation typeCu KαCu Kα
µ (mm1)0.650.67
Crystal size (mm)0.30 × 0.20 × 0.100.30 × 0.25 × 0.15
Data collection
DiffractometerEnraf Nonius CAD-4
diffractometer
Enraf Nonius CAD-4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
3002, 2612, 2443 2481, 2481, 2222
Rint0.0380.000
(sin θ/λ)max1)0.6170.601
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.062, 0.194, 1.15 0.043, 0.129, 0.80
No. of reflections26122481
No. of parameters298298
No. of restraints10
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.220.22, 0.23

Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, SDP (Frenz, 1984), SHELXS86 (Sheldrick, 1986), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97.

Selected geometric parameters (Å, º) for (I) top
O1—C31.223 (5)O4—C261.195 (6)
O2—C61.428 (4)O5—C231.325 (10)
O3—C261.344 (5)O5—C211.350 (6)
O3—C71.445 (4)
C26—O3—C7119.4 (3)O3—C7—C6106.5 (3)
C23—O5—C21105.5 (5)C8—C7—C6113.6 (3)
O1—C3—C2118.9 (4)O4—C26—O3124.7 (4)
O1—C3—C4121.2 (4)O4—C26—C27126.1 (4)
O2—C6—C5110.9 (3)O3—C26—C27109.2 (4)
O2—C6—C7106.7 (3)C20—C21—O5112.9 (5)
O3—C7—C8107.6 (3)O5—C23—C22111.9 (5)
O1—C3—C4—C2946.3 (6)C26—O3—C7—C6109.1 (3)
O1—C3—C4—C2868.7 (5)O2—C6—C7—O360.4 (4)
C4—C5—C6—O253.1 (4)
Hydrogen-bond geometry (Å, º) for (I) top
D—H···AH···AD···AD—H···A
O2—H2···O1i1.950 (6)2.768 (6)175 (4)
C1—H1···O5ii2.56 (6)3.325 (7)130 (4)
C23—H23···O4iii2.48 (8)3.472 (9)153 (5)
Symmetry codes: (i) x, y1/2, z+1; (ii) x+1, y+1/2, z; (iii) x, y, z1.
Selected geometric parameters (Å, º) for (II) top
O1—C31.220 (4)O4—C261.170 (4)
O2—C61.208 (3)O5—C231.345 (6)
O3—C261.336 (3)O5—C211.371 (5)
O3—C71.446 (3)
C26—O3—C7119.1 (2)C20—C21—O5111.5 (4)
C23—O5—C21105.8 (3)O5—C21—H21124.3
O1—C3—C2119.5 (3)O4—C26—O3121.9 (4)
O1—C3—C4121.3 (3)O4—C26—C27126.5 (3)
O3—C7—C6111.6 (2)O3—C26—C27111.6 (3)
O3—C7—C8105.9 (2)
O1—C3—C4—C2947.3 (4)C26—O3—C7—C670.4 (3)
O1—C3—C4—C2869.6 (4)O2—C6—C7—O3132.3 (3)
C4—C5—C6—O223.8 (4)
 

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