The crystal structures of six new crystals of oxo-cholic acids (oxo-CA) are reported: (I) 3α,12α-dihydroxy-7-oxo-5β-cholan-24-oic acid; (II) 3α,7α-dihydroxy-12-oxo-5β-cholan-24-oic acid; (III) 7α-hydroxy-3,12-dioxo-5β-cholan-24-oic acid; (IV-α) and (IV-β) 12α-hydroxy-3,7-dioxo-5β-cholan-24-oic acid; (V) 3,7,12-trihydroxy-5β-cholan-24-oic acid. (IV-β) is a pseudopolymorphic solvated form of (IV-α) and contains small channels which can trap disordered water molecules. In all the structures the four saturated cycles, forming the common alicyclic skeleton, have the same conformation, while the carboxylic side chain adopts flexible conformations in order to produce the most efficient crystal aggregations. The structures display a variety of supramolecular architectures dominated by networks of cooperative O—H
O hydrogen bonds forming different packing motifs often supported by weaker C—H
O interactions.
Supporting information
CCDC references: 274186; 274187; 274188; 274189; 274190; 274191
For all compounds, data collection: Kappa-CCD server software (Nonius, 1997); cell refinement: DENZO SMN (Otwinowski & Minor, 1997); data reduction: DENZO SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP III (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997), PARST (Nardelli, 1995), PLATON (Spek, 1999).
Crystal data top
C24H38O5 | Dx = 1.209 Mg m−3 |
Mr = 406.54 | Mo Kα radiation, λ = 0.71070 Å |
Orthorhombic, P212121 | Cell parameters from 3690 reflections |
a = 8.9879 (1) Å | θ = 3.8–28.0° |
b = 9.4028 (1) Å | µ = 0.08 mm−1 |
c = 26.4369 (4) Å | T = 295 K |
V = 2234.22 (5) Å3 | Prism, colourless |
Z = 4 | 0.42 × 0.35 × 0.28 mm |
F(000) = 888 | |
Data collection top
Nonius Kappa CCD diffractometer | 2385 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.041 |
Graphite monochromator | θmax = 28.0°, θmin = 3.8° |
ϕ scans and ω scans | h = −11→11 |
24241 measured reflections | k = −12→12 |
3049 independent reflections | l = −34→34 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.110 | w = 1/[σ2(Fo2) + (0.0534P)2 + 0.2792P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
3049 reflections | Δρmax = 0.15 e Å−3 |
277 parameters | Δρmin = −0.13 e Å−3 |
0 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −3.4 (15) |
Crystal data top
C24H38O5 | V = 2234.22 (5) Å3 |
Mr = 406.54 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 8.9879 (1) Å | µ = 0.08 mm−1 |
b = 9.4028 (1) Å | T = 295 K |
c = 26.4369 (4) Å | 0.42 × 0.35 × 0.28 mm |
Data collection top
Nonius Kappa CCD diffractometer | 2385 reflections with I > 2σ(I) |
24241 measured reflections | Rint = 0.041 |
3049 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.039 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.110 | Δρmax = 0.15 e Å−3 |
S = 1.04 | Δρmin = −0.13 e Å−3 |
3049 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
277 parameters | Absolute structure parameter: −3.4 (15) |
0 restraints | |
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 | x | y | z | Uiso*/Ueq | |
C1 | 0.2899 (2) | 0.5704 (3) | 0.09002 (9) | 0.0640 (6) | |
H1A | 0.2150 | 0.5468 | 0.0650 | 0.077* | |
H1B | 0.2452 | 0.5584 | 0.1231 | 0.077* | |
C2 | 0.3334 (3) | 0.7254 (3) | 0.08348 (9) | 0.0635 (6) | |
H2A | 0.2455 | 0.7847 | 0.0864 | 0.076* | |
H2B | 0.4021 | 0.7525 | 0.1101 | 0.076* | |
C3 | 0.4056 (3) | 0.7500 (3) | 0.03250 (9) | 0.0619 (6) | |
H3 | 0.3304 | 0.7382 | 0.0060 | 0.074* | |
C4 | 0.5320 (3) | 0.6470 (3) | 0.02285 (8) | 0.0557 (5) | |
H4A | 0.6147 | 0.6714 | 0.0448 | 0.067* | |
H4B | 0.5652 | 0.6579 | −0.0118 | 0.067* | |
C5 | 0.4901 (3) | 0.4906 (3) | 0.03182 (8) | 0.0557 (5) | |
H5 | 0.4160 | 0.4638 | 0.0064 | 0.067* | |
C6 | 0.6293 (3) | 0.3977 (3) | 0.02333 (8) | 0.0646 (6) | |
H6A | 0.6018 | 0.2979 | 0.0235 | 0.078* | |
H6B | 0.6734 | 0.4196 | −0.0092 | 0.078* | |
C7 | 0.7391 (2) | 0.4263 (3) | 0.06457 (8) | 0.0534 (5) | |
C8 | 0.6836 (2) | 0.3990 (2) | 0.11761 (7) | 0.0466 (5) | |
H8 | 0.6553 | 0.2986 | 0.1203 | 0.056* | |
C9 | 0.5422 (2) | 0.4919 (2) | 0.12564 (7) | 0.0462 (4) | |
H9 | 0.5742 | 0.5908 | 0.1213 | 0.055* | |
C10 | 0.4205 (2) | 0.4654 (3) | 0.08484 (8) | 0.0537 (5) | |
C11 | 0.4853 (2) | 0.4798 (3) | 0.18057 (8) | 0.0556 (5) | |
H11A | 0.4042 | 0.5466 | 0.1852 | 0.067* | |
H11B | 0.4458 | 0.3848 | 0.1857 | 0.067* | |
C12 | 0.6040 (2) | 0.5085 (3) | 0.22078 (7) | 0.0506 (5) | |
H12 | 0.5603 | 0.4839 | 0.2536 | 0.061* | |
C13 | 0.7394 (2) | 0.4101 (2) | 0.21293 (7) | 0.0431 (4) | |
C14 | 0.7974 (2) | 0.4317 (2) | 0.15823 (7) | 0.0432 (4) | |
H14 | 0.8224 | 0.5327 | 0.1549 | 0.052* | |
C15 | 0.9443 (2) | 0.3500 (3) | 0.15770 (8) | 0.0541 (5) | |
H15A | 1.0127 | 0.3903 | 0.1332 | 0.065* | |
H15B | 0.9281 | 0.2506 | 0.1496 | 0.065* | |
C16 | 1.0046 (2) | 0.3667 (3) | 0.21165 (8) | 0.0561 (6) | |
H16A | 1.0959 | 0.4218 | 0.2114 | 0.067* | |
H16B | 1.0254 | 0.2743 | 0.2263 | 0.067* | |
C17 | 0.8834 (2) | 0.4445 (2) | 0.24272 (7) | 0.0453 (4) | |
H17 | 0.9015 | 0.5466 | 0.2386 | 0.054* | |
C18 | 0.6910 (3) | 0.2566 (2) | 0.22346 (9) | 0.0561 (5) | |
H18A | 0.6332 | 0.2536 | 0.2540 | 0.067* | |
H18B | 0.7774 | 0.1976 | 0.2273 | 0.067* | |
H18C | 0.6320 | 0.2224 | 0.1957 | 0.067* | |
C19 | 0.3559 (3) | 0.3147 (3) | 0.08837 (11) | 0.0785 (8) | |
H19A | 0.3017 | 0.3048 | 0.1195 | 0.094* | |
H19B | 0.4355 | 0.2466 | 0.0876 | 0.094* | |
H19C | 0.2903 | 0.2983 | 0.0603 | 0.094* | |
C20 | 0.8902 (2) | 0.4133 (2) | 0.30027 (7) | 0.0511 (5) | |
H20 | 0.8593 | 0.3146 | 0.3059 | 0.061* | |
C21 | 0.7847 (3) | 0.5109 (3) | 0.32949 (8) | 0.0681 (7) | |
H21A | 0.8041 | 0.5026 | 0.3651 | 0.082* | |
H21B | 0.6837 | 0.4838 | 0.3227 | 0.082* | |
H21C | 0.8001 | 0.6075 | 0.3190 | 0.082* | |
C22 | 1.0507 (3) | 0.4298 (3) | 0.31846 (8) | 0.0572 (5) | |
H22A | 1.1121 | 0.3619 | 0.3003 | 0.069* | |
H22B | 1.0850 | 0.5242 | 0.3093 | 0.069* | |
C23 | 1.0761 (3) | 0.4089 (3) | 0.37480 (9) | 0.0696 (7) | |
H23A | 1.0311 | 0.4874 | 0.3930 | 0.083* | |
H23B | 1.0273 | 0.3220 | 0.3855 | 0.083* | |
C24 | 1.2379 (3) | 0.4007 (3) | 0.38822 (9) | 0.0608 (6) | |
O25 | 0.4613 (2) | 0.8939 (2) | 0.03084 (8) | 0.0791 (6) | |
O26 | 0.6460 (2) | 0.65463 (19) | 0.22323 (6) | 0.0626 (4) | |
O27 | 1.3292 (3) | 0.3376 (3) | 0.36384 (8) | 0.1006 (8) | |
O28 | 1.2734 (3) | 0.4657 (2) | 0.43049 (7) | 0.0815 (6) | |
O29 | 0.86061 (18) | 0.4784 (2) | 0.05647 (6) | 0.0717 (5) | |
H25 | 0.431 (4) | 0.935 (4) | 0.0040 (14) | 0.103 (11)* | |
H26 | 0.652 (4) | 0.692 (4) | 0.1941 (12) | 0.110 (12)* | |
H28 | 1.377 (5) | 0.442 (4) | 0.4406 (15) | 0.134 (14)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0351 (10) | 0.0919 (18) | 0.0650 (13) | −0.0003 (12) | −0.0031 (10) | −0.0075 (13) |
C2 | 0.0438 (11) | 0.0825 (17) | 0.0643 (13) | 0.0168 (12) | −0.0106 (10) | −0.0090 (12) |
C3 | 0.0528 (13) | 0.0708 (14) | 0.0622 (12) | 0.0065 (12) | −0.0167 (11) | −0.0002 (12) |
C4 | 0.0456 (11) | 0.0733 (15) | 0.0481 (10) | 0.0024 (11) | −0.0045 (9) | 0.0019 (10) |
C5 | 0.0472 (11) | 0.0693 (14) | 0.0505 (11) | 0.0010 (11) | −0.0062 (9) | −0.0103 (11) |
C6 | 0.0687 (15) | 0.0749 (16) | 0.0504 (11) | 0.0133 (14) | 0.0034 (11) | −0.0120 (11) |
C7 | 0.0492 (12) | 0.0620 (13) | 0.0490 (10) | 0.0151 (11) | 0.0101 (9) | 0.0013 (10) |
C8 | 0.0418 (10) | 0.0491 (11) | 0.0490 (10) | 0.0018 (9) | 0.0092 (8) | 0.0012 (9) |
C9 | 0.0358 (9) | 0.0537 (11) | 0.0491 (10) | 0.0004 (9) | 0.0044 (8) | −0.0007 (9) |
C10 | 0.0402 (10) | 0.0639 (13) | 0.0570 (11) | −0.0063 (10) | −0.0025 (9) | −0.0056 (10) |
C11 | 0.0364 (10) | 0.0762 (15) | 0.0541 (11) | 0.0066 (11) | 0.0101 (8) | 0.0001 (11) |
C12 | 0.0408 (10) | 0.0655 (13) | 0.0454 (10) | 0.0053 (10) | 0.0090 (8) | 0.0018 (10) |
C13 | 0.0366 (9) | 0.0474 (10) | 0.0451 (9) | 0.0012 (9) | 0.0095 (8) | 0.0059 (9) |
C14 | 0.0375 (9) | 0.0456 (10) | 0.0466 (9) | 0.0026 (9) | 0.0092 (8) | 0.0047 (8) |
C15 | 0.0404 (10) | 0.0689 (14) | 0.0530 (11) | 0.0108 (11) | 0.0111 (9) | 0.0071 (10) |
C16 | 0.0422 (10) | 0.0688 (14) | 0.0572 (12) | 0.0096 (11) | 0.0056 (9) | 0.0086 (11) |
C17 | 0.0403 (9) | 0.0471 (10) | 0.0485 (9) | 0.0001 (9) | 0.0052 (8) | 0.0086 (9) |
C18 | 0.0526 (12) | 0.0552 (12) | 0.0604 (12) | −0.0064 (11) | 0.0100 (10) | 0.0099 (11) |
C19 | 0.0684 (17) | 0.0791 (18) | 0.0878 (17) | −0.0240 (15) | −0.0042 (15) | −0.0072 (16) |
C20 | 0.0514 (11) | 0.0540 (12) | 0.0478 (10) | 0.0020 (11) | 0.0026 (9) | 0.0100 (10) |
C21 | 0.0646 (14) | 0.0885 (18) | 0.0512 (11) | 0.0107 (16) | 0.0079 (11) | 0.0044 (12) |
C22 | 0.0560 (12) | 0.0637 (14) | 0.0518 (11) | 0.0009 (12) | −0.0017 (10) | 0.0085 (11) |
C23 | 0.0683 (15) | 0.0861 (18) | 0.0543 (12) | 0.0019 (15) | −0.0045 (11) | 0.0075 (13) |
C24 | 0.0686 (15) | 0.0620 (14) | 0.0517 (11) | 0.0078 (13) | −0.0061 (11) | −0.0020 (11) |
O25 | 0.0903 (14) | 0.0728 (12) | 0.0742 (11) | 0.0061 (11) | −0.0358 (11) | 0.0123 (10) |
O26 | 0.0715 (11) | 0.0568 (9) | 0.0594 (9) | 0.0161 (8) | −0.0006 (9) | −0.0038 (8) |
O27 | 0.0858 (14) | 0.1320 (18) | 0.0840 (12) | 0.0418 (15) | −0.0294 (12) | −0.0405 (14) |
O28 | 0.0836 (13) | 0.0997 (15) | 0.0613 (10) | 0.0119 (12) | −0.0127 (10) | −0.0198 (10) |
O29 | 0.0493 (9) | 0.1111 (15) | 0.0549 (8) | 0.0082 (10) | 0.0129 (7) | 0.0217 (9) |
Geometric parameters (Å, º) top
C1—C2 | 1.519 (4) | C13—C17 | 1.549 (3) |
C1—C10 | 1.540 (3) | C13—C14 | 1.551 (2) |
C1—H1A | 0.9700 | C14—C15 | 1.528 (3) |
C1—H1B | 0.9700 | C14—H14 | 0.9800 |
C2—C3 | 1.514 (3) | C15—C16 | 1.534 (3) |
C2—H2A | 0.9700 | C15—H15A | 0.9700 |
C2—H2B | 0.9700 | C15—H15B | 0.9700 |
C3—O25 | 1.443 (3) | C16—C17 | 1.548 (3) |
C3—C4 | 1.514 (3) | C16—H16A | 0.9700 |
C3—H3 | 0.9800 | C16—H16B | 0.9700 |
C4—C5 | 1.536 (3) | C17—C20 | 1.551 (3) |
C4—H4A | 0.9700 | C17—H17 | 0.9800 |
C4—H4B | 0.9700 | C18—H18A | 0.9600 |
C5—C6 | 1.542 (3) | C18—H18B | 0.9600 |
C5—C10 | 1.553 (3) | C18—H18C | 0.9600 |
C5—H5 | 0.9800 | C19—H19A | 0.9600 |
C6—C7 | 1.495 (3) | C19—H19B | 0.9600 |
C6—H6A | 0.9700 | C19—H19C | 0.9600 |
C6—H6B | 0.9700 | C20—C22 | 1.529 (3) |
C7—O29 | 1.216 (3) | C20—C21 | 1.529 (3) |
C7—C8 | 1.510 (3) | C20—H20 | 0.9800 |
C8—C14 | 1.515 (3) | C21—H21A | 0.9600 |
C8—C9 | 1.557 (3) | C21—H21B | 0.9600 |
C8—H8 | 0.9800 | C21—H21C | 0.9600 |
C9—C11 | 1.544 (3) | C22—C23 | 1.519 (3) |
C9—C10 | 1.556 (3) | C22—H22A | 0.9700 |
C9—H9 | 0.9800 | C22—H22B | 0.9700 |
C10—C19 | 1.535 (4) | C23—C24 | 1.498 (4) |
C11—C12 | 1.530 (3) | C23—H23A | 0.9700 |
C11—H11A | 0.9700 | C23—H23B | 0.9700 |
C11—H11B | 0.9700 | C24—O27 | 1.200 (3) |
C12—O26 | 1.426 (3) | C24—O28 | 1.313 (3) |
C12—C13 | 1.543 (3) | O25—H25 | 0.85 (4) |
C12—H12 | 0.9800 | O26—H26 | 0.85 (3) |
C13—C18 | 1.533 (3) | O28—H28 | 1.00 (4) |
| | | |
C2—C1—C10 | 114.14 (19) | C12—C13—C17 | 117.75 (17) |
C2—C1—H1A | 108.7 | C18—C13—C14 | 112.83 (17) |
C10—C1—H1A | 108.7 | C12—C13—C14 | 108.20 (16) |
C2—C1—H1B | 108.7 | C17—C13—C14 | 99.54 (14) |
C10—C1—H1B | 108.7 | C8—C14—C15 | 118.35 (17) |
H1A—C1—H1B | 107.6 | C8—C14—C13 | 114.05 (15) |
C3—C2—C1 | 111.0 (2) | C15—C14—C13 | 103.50 (15) |
C3—C2—H2A | 109.4 | C8—C14—H14 | 106.7 |
C1—C2—H2A | 109.4 | C15—C14—H14 | 106.7 |
C3—C2—H2B | 109.4 | C13—C14—H14 | 106.7 |
C1—C2—H2B | 109.4 | C14—C15—C16 | 104.20 (17) |
H2A—C2—H2B | 108.0 | C14—C15—H15A | 110.9 |
O25—C3—C2 | 108.6 (2) | C16—C15—H15A | 110.9 |
O25—C3—C4 | 109.5 (2) | C14—C15—H15B | 110.9 |
C2—C3—C4 | 112.0 (2) | C16—C15—H15B | 110.9 |
O25—C3—H3 | 108.9 | H15A—C15—H15B | 108.9 |
C2—C3—H3 | 108.9 | C15—C16—C17 | 107.04 (17) |
C4—C3—H3 | 108.9 | C15—C16—H16A | 110.3 |
C3—C4—C5 | 113.76 (19) | C17—C16—H16A | 110.3 |
C3—C4—H4A | 108.8 | C15—C16—H16B | 110.3 |
C5—C4—H4A | 108.8 | C17—C16—H16B | 110.3 |
C3—C4—H4B | 108.8 | H16A—C16—H16B | 108.6 |
C5—C4—H4B | 108.8 | C16—C17—C13 | 102.71 (16) |
H4A—C4—H4B | 107.7 | C16—C17—C20 | 113.80 (17) |
C4—C5—C6 | 108.7 (2) | C13—C17—C20 | 119.50 (16) |
C4—C5—C10 | 112.55 (18) | C16—C17—H17 | 106.7 |
C6—C5—C10 | 111.83 (19) | C13—C17—H17 | 106.7 |
C4—C5—H5 | 107.8 | C20—C17—H17 | 106.7 |
C6—C5—H5 | 107.8 | C13—C18—H18A | 109.5 |
C10—C5—H5 | 107.8 | C13—C18—H18B | 109.5 |
C7—C6—C5 | 109.09 (17) | H18A—C18—H18B | 109.5 |
C7—C6—H6A | 109.9 | C13—C18—H18C | 109.5 |
C5—C6—H6A | 109.9 | H18A—C18—H18C | 109.5 |
C7—C6—H6B | 109.9 | H18B—C18—H18C | 109.5 |
C5—C6—H6B | 109.9 | C10—C19—H19A | 109.5 |
H6A—C6—H6B | 108.3 | C10—C19—H19B | 109.5 |
O29—C7—C6 | 122.5 (2) | H19A—C19—H19B | 109.5 |
O29—C7—C8 | 121.9 (2) | C10—C19—H19C | 109.5 |
C6—C7—C8 | 115.39 (19) | H19A—C19—H19C | 109.5 |
C7—C8—C14 | 113.63 (16) | H19B—C19—H19C | 109.5 |
C7—C8—C9 | 107.49 (16) | C22—C20—C21 | 111.4 (2) |
C14—C8—C9 | 109.91 (16) | C22—C20—C17 | 109.08 (17) |
C7—C8—H8 | 108.6 | C21—C20—C17 | 110.97 (18) |
C14—C8—H8 | 108.6 | C22—C20—H20 | 108.4 |
C9—C8—H8 | 108.6 | C21—C20—H20 | 108.4 |
C11—C9—C10 | 114.04 (16) | C17—C20—H20 | 108.4 |
C11—C9—C8 | 110.94 (17) | C20—C21—H21A | 109.5 |
C10—C9—C8 | 112.92 (16) | C20—C21—H21B | 109.5 |
C11—C9—H9 | 106.1 | H21A—C21—H21B | 109.5 |
C10—C9—H9 | 106.1 | C20—C21—H21C | 109.5 |
C8—C9—H9 | 106.1 | H21A—C21—H21C | 109.5 |
C19—C10—C1 | 107.37 (19) | H21B—C21—H21C | 109.5 |
C19—C10—C5 | 110.4 (2) | C23—C22—C20 | 115.9 (2) |
C1—C10—C5 | 106.85 (19) | C23—C22—H22A | 108.3 |
C19—C10—C9 | 111.8 (2) | C20—C22—H22A | 108.3 |
C1—C10—C9 | 111.81 (18) | C23—C22—H22B | 108.3 |
C5—C10—C9 | 108.55 (17) | C20—C22—H22B | 108.3 |
C12—C11—C9 | 114.17 (16) | H22A—C22—H22B | 107.4 |
C12—C11—H11A | 108.7 | C24—C23—C22 | 112.6 (2) |
C9—C11—H11A | 108.7 | C24—C23—H23A | 109.1 |
C12—C11—H11B | 108.7 | C22—C23—H23A | 109.1 |
C9—C11—H11B | 108.7 | C24—C23—H23B | 109.1 |
H11A—C11—H11B | 107.6 | C22—C23—H23B | 109.1 |
O26—C12—C11 | 112.74 (19) | H23A—C23—H23B | 107.8 |
O26—C12—C13 | 112.02 (17) | O27—C24—O28 | 121.4 (2) |
C11—C12—C13 | 110.52 (17) | O27—C24—C23 | 124.2 (2) |
O26—C12—H12 | 107.1 | O28—C24—C23 | 114.4 (2) |
C11—C12—H12 | 107.1 | C3—O25—H25 | 110 (2) |
C13—C12—H12 | 107.1 | C12—O26—H26 | 112 (2) |
C18—C13—C12 | 108.45 (16) | C24—O28—H28 | 111 (2) |
C18—C13—C17 | 109.94 (17) | | |
Crystal data top
C24H38O5 | Dx = 1.225 Mg m−3 |
Mr = 406.54 | Mo Kα radiation, λ = 0.71070 Å |
Orthorhombic, P212121 | Cell parameters from 2878 reflections |
a = 6.3122 (1) Å | θ = 3.7–28.0° |
b = 10.8884 (2) Å | µ = 0.08 mm−1 |
c = 32.0624 (7) Å | T = 295 K |
V = 2203.64 (7) Å3 | Prism, colourless |
Z = 4 | 0.36 × 0.14 × 0.10 mm |
F(000) = 888 | |
Data collection top
Nonius Kappa CCD diffractometer | 2415 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.076 |
Graphite monochromator | θmax = 28.0°, θmin = 3.7° |
ϕ scans and ω scans | h = −8→8 |
13705 measured reflections | k = −14→14 |
3006 independent reflections | l = −41→42 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.120 | w = 1/[σ2(Fo2) + (0.0556P)2 + 0.316P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
3006 reflections | Δρmax = 0.16 e Å−3 |
277 parameters | Δρmin = −0.16 e Å−3 |
0 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 1.2 (15) |
Crystal data top
C24H38O5 | V = 2203.64 (7) Å3 |
Mr = 406.54 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 6.3122 (1) Å | µ = 0.08 mm−1 |
b = 10.8884 (2) Å | T = 295 K |
c = 32.0624 (7) Å | 0.36 × 0.14 × 0.10 mm |
Data collection top
Nonius Kappa CCD diffractometer | 2415 reflections with I > 2σ(I) |
13705 measured reflections | Rint = 0.076 |
3006 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.120 | Δρmax = 0.16 e Å−3 |
S = 1.04 | Δρmin = −0.16 e Å−3 |
3006 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
277 parameters | Absolute structure parameter: 1.2 (15) |
0 restraints | |
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 | x | y | z | Uiso*/Ueq | |
C1 | 0.6355 (5) | 1.2414 (2) | 0.30325 (8) | 0.0532 (6) | |
H1A | 0.5160 | 1.2620 | 0.2856 | 0.064* | |
H1B | 0.6470 | 1.3048 | 0.3244 | 0.064* | |
C2 | 0.8364 (5) | 1.2430 (2) | 0.27674 (8) | 0.0509 (6) | |
H2A | 0.8495 | 1.3219 | 0.2629 | 0.061* | |
H2B | 0.9593 | 1.2318 | 0.2945 | 0.061* | |
C3 | 0.8280 (4) | 1.1414 (2) | 0.24449 (7) | 0.0459 (5) | |
H3 | 0.7114 | 1.1581 | 0.2251 | 0.055* | |
C4 | 0.7928 (4) | 1.0181 (2) | 0.26448 (7) | 0.0457 (5) | |
H4A | 0.9148 | 0.9979 | 0.2815 | 0.055* | |
H4B | 0.7812 | 0.9563 | 0.2428 | 0.055* | |
C5 | 0.5930 (4) | 1.0144 (2) | 0.29169 (7) | 0.0489 (6) | |
H5A | 0.4723 | 1.0289 | 0.2731 | 0.059* | |
C6 | 0.5608 (5) | 0.8869 (3) | 0.31102 (8) | 0.0566 (7) | |
H6A | 0.4154 | 0.8804 | 0.3206 | 0.068* | |
H6B | 0.5813 | 0.8255 | 0.2895 | 0.068* | |
C7 | 0.7072 (4) | 0.8572 (2) | 0.34730 (7) | 0.0485 (6) | |
H7 | 0.6565 | 0.7819 | 0.3607 | 0.058* | |
C8 | 0.7078 (4) | 0.9600 (2) | 0.37976 (7) | 0.0401 (5) | |
H8 | 0.5655 | 0.9643 | 0.3919 | 0.048* | |
C9 | 0.7553 (4) | 1.0860 (2) | 0.35923 (7) | 0.0374 (5) | |
H9 | 0.8905 | 1.0762 | 0.3446 | 0.045* | |
C10 | 0.5886 (4) | 1.1177 (2) | 0.32515 (7) | 0.0458 (6) | |
C11 | 0.7898 (4) | 1.1899 (2) | 0.39118 (7) | 0.0457 (5) | |
H11A | 0.8616 | 1.2573 | 0.3774 | 0.055* | |
H11B | 0.6525 | 1.2196 | 0.4003 | 0.055* | |
C12 | 0.9175 (4) | 1.1533 (2) | 0.42950 (7) | 0.0417 (5) | |
C13 | 0.8506 (3) | 1.0350 (2) | 0.45024 (6) | 0.0368 (5) | |
C14 | 0.8629 (4) | 0.9380 (2) | 0.41498 (6) | 0.0378 (5) | |
H14 | 1.0052 | 0.9441 | 0.4029 | 0.045* | |
C15 | 0.8549 (5) | 0.8172 (2) | 0.43895 (7) | 0.0490 (6) | |
H15A | 0.9088 | 0.7500 | 0.4222 | 0.059* | |
H15B | 0.7114 | 0.7982 | 0.4476 | 0.059* | |
C16 | 0.9976 (5) | 0.8409 (2) | 0.47664 (8) | 0.0539 (7) | |
H16A | 1.1379 | 0.8074 | 0.4718 | 0.065* | |
H16B | 0.9388 | 0.8024 | 0.5014 | 0.065* | |
C17 | 1.0095 (4) | 0.9831 (2) | 0.48253 (7) | 0.0392 (5) | |
H17 | 1.1502 | 1.0073 | 0.4725 | 0.047* | |
C18 | 0.6251 (4) | 1.0511 (3) | 0.46784 (7) | 0.0496 (6) | |
H18A | 0.5336 | 1.0823 | 0.4464 | 0.060* | |
H18B | 0.6284 | 1.1078 | 0.4907 | 0.060* | |
H18C | 0.5728 | 0.9732 | 0.4773 | 0.060* | |
C19 | 0.3648 (4) | 1.1276 (3) | 0.34388 (9) | 0.0680 (8) | |
H19A | 0.2645 | 1.1435 | 0.3220 | 0.082* | |
H19B | 0.3612 | 1.1936 | 0.3637 | 0.082* | |
H19C | 0.3292 | 1.0520 | 0.3576 | 0.082* | |
C20 | 0.9966 (3) | 1.0296 (2) | 0.52814 (7) | 0.0392 (5) | |
H20 | 0.9455 | 1.1145 | 0.5276 | 0.047* | |
C21 | 1.2203 (4) | 1.0298 (3) | 0.54682 (8) | 0.0529 (6) | |
H21A | 1.3038 | 1.0923 | 0.5336 | 0.064* | |
H21B | 1.2852 | 0.9511 | 0.5424 | 0.064* | |
H21C | 1.2120 | 1.0460 | 0.5762 | 0.064* | |
C22 | 0.8495 (4) | 0.9551 (2) | 0.55686 (6) | 0.0419 (5) | |
H22A | 0.7213 | 0.9346 | 0.5417 | 0.050* | |
H22B | 0.9192 | 0.8789 | 0.5644 | 0.050* | |
C23 | 0.7903 (4) | 1.0241 (2) | 0.59641 (7) | 0.0484 (6) | |
H23A | 0.9181 | 1.0568 | 0.6090 | 0.058* | |
H23B | 0.7003 | 1.0930 | 0.5891 | 0.058* | |
C24 | 0.6776 (4) | 0.9465 (2) | 0.62792 (7) | 0.0475 (6) | |
O25 | 1.0238 (3) | 1.13399 (19) | 0.22117 (5) | 0.0537 (5) | |
O26 | 1.0688 (3) | 1.21337 (17) | 0.44101 (6) | 0.0603 (5) | |
O27 | 0.6826 (4) | 0.83553 (19) | 0.62793 (6) | 0.0695 (6) | |
O28 | 0.5780 (4) | 1.0114 (2) | 0.65676 (6) | 0.0706 (6) | |
O29 | 0.9180 (3) | 0.83479 (16) | 0.33116 (5) | 0.0517 (4) | |
H25 | 1.046 (5) | 1.211 (4) | 0.2099 (10) | 0.083 (11)* | |
H28 | 0.531 (7) | 0.963 (4) | 0.6783 (16) | 0.128 (17)* | |
H29 | 0.987 (6) | 0.783 (3) | 0.3514 (10) | 0.082 (11)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0611 (16) | 0.0530 (14) | 0.0454 (13) | 0.0175 (13) | −0.0064 (12) | 0.0040 (11) |
C2 | 0.0661 (17) | 0.0428 (12) | 0.0438 (12) | 0.0024 (12) | −0.0054 (12) | 0.0077 (10) |
C3 | 0.0515 (13) | 0.0513 (13) | 0.0348 (11) | 0.0041 (12) | −0.0061 (10) | 0.0063 (10) |
C4 | 0.0534 (13) | 0.0468 (12) | 0.0368 (11) | −0.0001 (12) | −0.0034 (10) | 0.0014 (10) |
C5 | 0.0441 (13) | 0.0601 (15) | 0.0425 (12) | −0.0048 (12) | −0.0090 (10) | 0.0021 (11) |
C6 | 0.0597 (16) | 0.0633 (16) | 0.0469 (13) | −0.0237 (14) | −0.0055 (12) | 0.0006 (12) |
C7 | 0.0642 (15) | 0.0419 (12) | 0.0394 (12) | −0.0134 (12) | 0.0017 (11) | −0.0010 (10) |
C8 | 0.0408 (11) | 0.0418 (12) | 0.0376 (10) | −0.0050 (10) | 0.0036 (9) | 0.0007 (9) |
C9 | 0.0357 (11) | 0.0395 (11) | 0.0370 (11) | 0.0003 (9) | 0.0012 (8) | 0.0004 (9) |
C10 | 0.0377 (11) | 0.0565 (14) | 0.0432 (12) | 0.0058 (12) | −0.0020 (10) | 0.0028 (11) |
C11 | 0.0586 (14) | 0.0384 (11) | 0.0402 (12) | 0.0041 (11) | −0.0018 (11) | 0.0030 (10) |
C12 | 0.0509 (13) | 0.0370 (11) | 0.0372 (11) | 0.0020 (11) | 0.0032 (10) | −0.0044 (9) |
C13 | 0.0398 (11) | 0.0383 (11) | 0.0324 (10) | 0.0016 (9) | 0.0051 (9) | 0.0006 (9) |
C14 | 0.0424 (11) | 0.0358 (10) | 0.0354 (10) | −0.0025 (10) | 0.0052 (9) | 0.0007 (9) |
C15 | 0.0711 (17) | 0.0357 (11) | 0.0404 (12) | −0.0002 (12) | 0.0052 (12) | 0.0024 (9) |
C16 | 0.0775 (18) | 0.0435 (13) | 0.0405 (12) | 0.0163 (13) | 0.0016 (12) | −0.0018 (10) |
C17 | 0.0403 (11) | 0.0430 (11) | 0.0344 (10) | 0.0046 (10) | 0.0060 (9) | 0.0015 (9) |
C18 | 0.0424 (12) | 0.0663 (16) | 0.0401 (11) | 0.0068 (12) | 0.0072 (10) | 0.0004 (11) |
C19 | 0.0421 (14) | 0.095 (2) | 0.0669 (17) | 0.0128 (16) | 0.0030 (13) | 0.0046 (18) |
C20 | 0.0419 (11) | 0.0393 (11) | 0.0363 (10) | −0.0021 (10) | 0.0030 (9) | −0.0010 (10) |
C21 | 0.0471 (13) | 0.0625 (16) | 0.0492 (14) | −0.0070 (12) | −0.0005 (11) | −0.0095 (13) |
C22 | 0.0485 (12) | 0.0431 (12) | 0.0340 (10) | −0.0051 (10) | 0.0030 (9) | 0.0009 (9) |
C23 | 0.0609 (14) | 0.0446 (12) | 0.0398 (12) | 0.0005 (12) | 0.0097 (11) | 0.0006 (10) |
C24 | 0.0574 (14) | 0.0526 (14) | 0.0324 (11) | 0.0014 (13) | 0.0024 (10) | 0.0005 (10) |
O25 | 0.0641 (11) | 0.0591 (11) | 0.0379 (8) | −0.0029 (10) | 0.0018 (8) | 0.0070 (8) |
O26 | 0.0708 (12) | 0.0483 (10) | 0.0619 (11) | −0.0164 (10) | −0.0105 (10) | 0.0074 (9) |
O27 | 0.0963 (15) | 0.0564 (12) | 0.0557 (11) | −0.0108 (12) | 0.0254 (11) | 0.0022 (9) |
O28 | 0.0982 (16) | 0.0664 (13) | 0.0471 (10) | 0.0147 (13) | 0.0263 (11) | 0.0054 (10) |
O29 | 0.0739 (12) | 0.0427 (9) | 0.0383 (8) | 0.0067 (9) | 0.0004 (8) | −0.0018 (7) |
Geometric parameters (Å, º) top
C1—C2 | 1.527 (4) | C13—C17 | 1.548 (3) |
C1—C10 | 1.548 (4) | C13—C14 | 1.549 (3) |
C1—H1A | 0.9700 | C14—C15 | 1.524 (3) |
C1—H1B | 0.9700 | C14—H14 | 0.9800 |
C2—C3 | 1.515 (3) | C15—C16 | 1.529 (4) |
C2—H2A | 0.9700 | C15—H15A | 0.9700 |
C2—H2B | 0.9700 | C15—H15B | 0.9700 |
C3—O25 | 1.447 (3) | C16—C17 | 1.562 (3) |
C3—C4 | 1.504 (3) | C16—H16A | 0.9700 |
C3—H3 | 0.9800 | C16—H16B | 0.9700 |
C4—C5 | 1.534 (3) | C17—C20 | 1.550 (3) |
C4—H4A | 0.9700 | C17—H17 | 0.9800 |
C4—H4B | 0.9700 | C18—H18A | 0.9600 |
C5—C6 | 1.534 (4) | C18—H18B | 0.9600 |
C5—C10 | 1.554 (4) | C18—H18C | 0.9600 |
C5—H5A | 0.9800 | C19—H19A | 0.9600 |
C6—C7 | 1.520 (4) | C19—H19B | 0.9600 |
C6—H6A | 0.9700 | C19—H19C | 0.9600 |
C6—H6B | 0.9700 | C20—C21 | 1.534 (3) |
C7—O29 | 1.448 (3) | C20—C22 | 1.538 (3) |
C7—C8 | 1.529 (3) | C20—H20 | 0.9800 |
C7—H7 | 0.9800 | C21—H21A | 0.9600 |
C8—C14 | 1.514 (3) | C21—H21B | 0.9600 |
C8—C9 | 1.551 (3) | C21—H21C | 0.9600 |
C8—H8 | 0.9800 | C22—C23 | 1.520 (3) |
C9—C11 | 1.541 (3) | C22—H22A | 0.9700 |
C9—C10 | 1.556 (3) | C22—H22B | 0.9700 |
C9—H9 | 0.9800 | C23—C24 | 1.497 (3) |
C10—C19 | 1.539 (4) | C23—H23A | 0.9700 |
C11—C12 | 1.523 (3) | C23—H23B | 0.9700 |
C11—H11A | 0.9700 | C24—O27 | 1.208 (3) |
C11—H11B | 0.9700 | C24—O28 | 1.323 (3) |
C12—O26 | 1.215 (3) | O25—H25 | 0.92 (4) |
C12—C13 | 1.509 (3) | O28—H28 | 0.92 (5) |
C13—C18 | 1.541 (3) | O29—H29 | 0.96 (4) |
| | | |
C2—C1—C10 | 114.9 (2) | C18—C13—C17 | 113.27 (17) |
C2—C1—H1A | 108.5 | C12—C13—C14 | 104.26 (16) |
C10—C1—H1A | 108.5 | C18—C13—C14 | 113.02 (19) |
C2—C1—H1B | 108.5 | C17—C13—C14 | 101.94 (17) |
C10—C1—H1B | 108.5 | C8—C14—C15 | 119.4 (2) |
H1A—C1—H1B | 107.5 | C8—C14—C13 | 113.82 (18) |
C3—C2—C1 | 110.0 (2) | C15—C14—C13 | 102.63 (16) |
C3—C2—H2A | 109.7 | C8—C14—H14 | 106.7 |
C1—C2—H2A | 109.7 | C15—C14—H14 | 106.7 |
C3—C2—H2B | 109.7 | C13—C14—H14 | 106.7 |
C1—C2—H2B | 109.7 | C14—C15—C16 | 103.5 (2) |
H2A—C2—H2B | 108.2 | C14—C15—H15A | 111.1 |
O25—C3—C4 | 107.2 (2) | C16—C15—H15A | 111.1 |
O25—C3—C2 | 111.3 (2) | C14—C15—H15B | 111.1 |
C4—C3—C2 | 111.47 (18) | C16—C15—H15B | 111.1 |
O25—C3—H3 | 108.9 | H15A—C15—H15B | 109.0 |
C4—C3—H3 | 108.9 | C15—C16—C17 | 106.9 (2) |
C2—C3—H3 | 108.9 | C15—C16—H16A | 110.3 |
C3—C4—C5 | 112.8 (2) | C17—C16—H16A | 110.3 |
C3—C4—H4A | 109.0 | C15—C16—H16B | 110.3 |
C5—C4—H4A | 109.0 | C17—C16—H16B | 110.3 |
C3—C4—H4B | 109.0 | H16A—C16—H16B | 108.6 |
C5—C4—H4B | 109.0 | C13—C17—C20 | 118.56 (18) |
H4A—C4—H4B | 107.8 | C13—C17—C16 | 104.45 (19) |
C4—C5—C6 | 111.3 (2) | C20—C17—C16 | 115.8 (2) |
C4—C5—C10 | 112.8 (2) | C13—C17—H17 | 105.7 |
C6—C5—C10 | 111.9 (2) | C20—C17—H17 | 105.7 |
C4—C5—H5A | 106.8 | C16—C17—H17 | 105.7 |
C6—C5—H5A | 106.8 | C13—C18—H18A | 109.5 |
C10—C5—H5A | 106.8 | C13—C18—H18B | 109.5 |
C7—C6—C5 | 114.9 (2) | H18A—C18—H18B | 109.5 |
C7—C6—H6A | 108.5 | C13—C18—H18C | 109.5 |
C5—C6—H6A | 108.5 | H18A—C18—H18C | 109.5 |
C7—C6—H6B | 108.5 | H18B—C18—H18C | 109.5 |
C5—C6—H6B | 108.5 | C10—C19—H19A | 109.5 |
H6A—C6—H6B | 107.5 | C10—C19—H19B | 109.5 |
O29—C7—C6 | 108.7 (2) | H19A—C19—H19B | 109.5 |
O29—C7—C8 | 111.38 (19) | C10—C19—H19C | 109.5 |
C6—C7—C8 | 111.5 (2) | H19A—C19—H19C | 109.5 |
O29—C7—H7 | 108.4 | H19B—C19—H19C | 109.5 |
C6—C7—H7 | 108.4 | C21—C20—C22 | 108.82 (19) |
C8—C7—H7 | 108.4 | C21—C20—C17 | 108.69 (19) |
C14—C8—C7 | 113.17 (19) | C22—C20—C17 | 115.13 (19) |
C14—C8—C9 | 109.37 (18) | C21—C20—H20 | 108.0 |
C7—C8—C9 | 111.05 (17) | C22—C20—H20 | 108.0 |
C14—C8—H8 | 107.7 | C17—C20—H20 | 108.0 |
C7—C8—H8 | 107.7 | C20—C21—H21A | 109.5 |
C9—C8—H8 | 107.7 | C20—C21—H21B | 109.5 |
C11—C9—C8 | 113.21 (17) | H21A—C21—H21B | 109.5 |
C11—C9—C10 | 113.57 (19) | C20—C21—H21C | 109.5 |
C8—C9—C10 | 111.30 (19) | H21A—C21—H21C | 109.5 |
C11—C9—H9 | 106.0 | H21B—C21—H21C | 109.5 |
C8—C9—H9 | 106.0 | C23—C22—C20 | 112.80 (19) |
C10—C9—H9 | 106.0 | C23—C22—H22A | 109.0 |
C19—C10—C1 | 106.9 (2) | C20—C22—H22A | 109.0 |
C19—C10—C5 | 109.7 (2) | C23—C22—H22B | 109.0 |
C1—C10—C5 | 108.26 (19) | C20—C22—H22B | 109.0 |
C19—C10—C9 | 111.2 (2) | H22A—C22—H22B | 107.8 |
C1—C10—C9 | 112.5 (2) | C24—C23—C22 | 113.6 (2) |
C5—C10—C9 | 108.21 (19) | C24—C23—H23A | 108.8 |
C12—C11—C9 | 114.78 (18) | C22—C23—H23A | 108.8 |
C12—C11—H11A | 108.6 | C24—C23—H23B | 108.8 |
C9—C11—H11A | 108.6 | C22—C23—H23B | 108.8 |
C12—C11—H11B | 108.6 | H23A—C23—H23B | 107.7 |
C9—C11—H11B | 108.6 | O27—C24—O28 | 123.1 (2) |
H11A—C11—H11B | 107.5 | O27—C24—C23 | 123.5 (2) |
O26—C12—C13 | 123.1 (2) | O28—C24—C23 | 113.3 (2) |
O26—C12—C11 | 121.3 (2) | C3—O25—H25 | 106 (2) |
C13—C12—C11 | 115.5 (2) | C24—O28—H28 | 112 (3) |
C12—C13—C18 | 108.82 (19) | C7—O29—H29 | 106 (2) |
C12—C13—C17 | 115.11 (19) | | |
Crystal data top
C24H36O5 | F(000) = 440 |
Mr = 404.53 | Dx = 1.209 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.2677 (4) Å | Cell parameters from 2705 reflections |
b = 7.1108 (2) Å | θ = 3.4–27.5° |
c = 15.2270 (6) Å | µ = 0.08 mm−1 |
β = 92.340 (1)° | T = 295 K |
V = 1110.82 (7) Å3 | Irregular, colourless |
Z = 2 | 0.25 × 0.11 × 0.06 mm |
Data collection top
Nonius Kappa CCD diffractometer | 2236 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.039 |
Graphite monochromator | θmax = 27.5°, θmin = 3.4° |
ϕ scans and ω scans | h = −13→13 |
14953 measured reflections | k = −8→9 |
2721 independent reflections | l = −19→19 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.107 | w = 1/[σ2(Fo2) + (0.0521P)2 + 0.1088P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
2721 reflections | Δρmax = 0.15 e Å−3 |
273 parameters | Δρmin = −0.14 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.2 (14) |
Crystal data top
C24H36O5 | V = 1110.82 (7) Å3 |
Mr = 404.53 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 10.2677 (4) Å | µ = 0.08 mm−1 |
b = 7.1108 (2) Å | T = 295 K |
c = 15.2270 (6) Å | 0.25 × 0.11 × 0.06 mm |
β = 92.340 (1)° | |
Data collection top
Nonius Kappa CCD diffractometer | 2236 reflections with I > 2σ(I) |
14953 measured reflections | Rint = 0.039 |
2721 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.041 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.107 | Δρmax = 0.15 e Å−3 |
S = 1.05 | Δρmin = −0.14 e Å−3 |
2721 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
273 parameters | Absolute structure parameter: 0.2 (14) |
1 restraint | |
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 | x | y | z | Uiso*/Ueq | |
C1 | 0.9533 (2) | 0.1625 (4) | 0.25059 (16) | 0.0542 (6) | |
H1A | 0.9865 | 0.0374 | 0.2634 | 0.065* | |
H1B | 0.9234 | 0.1642 | 0.1893 | 0.065* | |
C2 | 1.0654 (2) | 0.3026 (4) | 0.26290 (15) | 0.0550 (6) | |
H2A | 1.1372 | 0.2669 | 0.2270 | 0.066* | |
H2B | 1.0366 | 0.4277 | 0.2457 | 0.066* | |
C3 | 1.1076 (2) | 0.3000 (4) | 0.35795 (17) | 0.0572 (6) | |
C4 | 1.0023 (2) | 0.3467 (4) | 0.41828 (16) | 0.0615 (7) | |
H4A | 0.9746 | 0.4756 | 0.4082 | 0.074* | |
H4B | 1.0359 | 0.3369 | 0.4786 | 0.074* | |
C5 | 0.8837 (2) | 0.2147 (4) | 0.40487 (15) | 0.0554 (6) | |
H5 | 0.9136 | 0.0890 | 0.4228 | 0.083* | |
C6 | 0.7745 (3) | 0.2675 (5) | 0.46631 (16) | 0.0671 (8) | |
H6A | 0.7171 | 0.1602 | 0.4715 | 0.081* | |
H6B | 0.8131 | 0.2934 | 0.5243 | 0.081* | |
C7 | 0.6929 (3) | 0.4378 (4) | 0.43632 (15) | 0.0591 (7) | |
H7 | 0.6172 | 0.4466 | 0.4733 | 0.089* | |
C8 | 0.6440 (2) | 0.4129 (3) | 0.34059 (13) | 0.0439 (5) | |
H8 | 0.5898 | 0.2994 | 0.3374 | 0.066* | |
C9 | 0.7611 (2) | 0.3816 (3) | 0.28156 (13) | 0.0391 (4) | |
H9 | 0.8216 | 0.4856 | 0.2941 | 0.059* | |
C10 | 0.8359 (2) | 0.1984 (3) | 0.30752 (15) | 0.0466 (5) | |
C11 | 0.7236 (2) | 0.3935 (4) | 0.18204 (13) | 0.0474 (5) | |
H11A | 0.8020 | 0.4131 | 0.1498 | 0.057* | |
H11B | 0.6857 | 0.2746 | 0.1630 | 0.057* | |
C12 | 0.62894 (19) | 0.5484 (4) | 0.15978 (13) | 0.0439 (5) | |
C13 | 0.50485 (19) | 0.5451 (3) | 0.21048 (14) | 0.0416 (5) | |
C14 | 0.5613 (2) | 0.5767 (3) | 0.30637 (14) | 0.0451 (5) | |
H14 | 0.6181 | 0.6874 | 0.3053 | 0.068* | |
C15 | 0.4415 (2) | 0.6312 (5) | 0.35711 (17) | 0.0617 (7) | |
H15A | 0.4659 | 0.7110 | 0.4068 | 0.074* | |
H15B | 0.3980 | 0.5201 | 0.3785 | 0.074* | |
C16 | 0.3528 (2) | 0.7377 (5) | 0.29039 (18) | 0.0654 (7) | |
H16A | 0.3486 | 0.8697 | 0.3061 | 0.078* | |
H16B | 0.2653 | 0.6863 | 0.2897 | 0.078* | |
C17 | 0.4122 (2) | 0.7146 (4) | 0.19813 (15) | 0.0483 (5) | |
H17 | 0.4660 | 0.8257 | 0.1880 | 0.072* | |
C18 | 0.4320 (2) | 0.3557 (4) | 0.20043 (17) | 0.0520 (6) | |
H18A | 0.3966 | 0.3437 | 0.1414 | 0.062* | |
H18B | 0.3625 | 0.3515 | 0.2407 | 0.062* | |
H18C | 0.4915 | 0.2543 | 0.2130 | 0.062* | |
C19 | 0.7487 (3) | 0.0228 (4) | 0.2959 (2) | 0.0697 (8) | |
H19A | 0.6731 | 0.0366 | 0.3304 | 0.084* | |
H19B | 0.7966 | −0.0867 | 0.3150 | 0.084* | |
H19C | 0.7221 | 0.0093 | 0.2350 | 0.084* | |
C20 | 0.3070 (2) | 0.7059 (4) | 0.12353 (16) | 0.0527 (6) | |
H20 | 0.2474 | 0.6027 | 0.1364 | 0.079* | |
C21 | 0.3640 (3) | 0.6674 (5) | 0.03331 (17) | 0.0696 (8) | |
H21A | 0.4221 | 0.7677 | 0.0190 | 0.084* | |
H21B | 0.2945 | 0.6599 | −0.0107 | 0.084* | |
H21C | 0.4111 | 0.5508 | 0.0354 | 0.084* | |
C22 | 0.2280 (2) | 0.8896 (4) | 0.1212 (2) | 0.0664 (7) | |
H22A | 0.2046 | 0.9191 | 0.1807 | 0.080* | |
H22B | 0.2841 | 0.9899 | 0.1018 | 0.080* | |
C23 | 0.1042 (2) | 0.8902 (5) | 0.0627 (2) | 0.0708 (8) | |
H23A | 0.0805 | 1.0197 | 0.0501 | 0.085* | |
H23B | 0.1231 | 0.8307 | 0.0074 | 0.085* | |
C24 | −0.0105 (2) | 0.7936 (4) | 0.09961 (16) | 0.0505 (5) | |
O25 | 1.21663 (18) | 0.2517 (4) | 0.38315 (13) | 0.0844 (7) | |
O26 | 0.65618 (14) | 0.6763 (3) | 0.11074 (11) | 0.0599 (5) | |
O27 | −0.00987 (17) | 0.7082 (3) | 0.16702 (14) | 0.0729 (6) | |
O28 | −0.11792 (17) | 0.8183 (3) | 0.04931 (13) | 0.0657 (5) | |
H28 | −0.181 (3) | 0.767 (6) | 0.074 (2) | 0.092 (12)* | |
O29 | 0.7630 (2) | 0.6109 (3) | 0.44259 (13) | 0.0698 (6) | |
H29 | 0.772 (4) | 0.652 (7) | 0.505 (3) | 0.116 (13)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0516 (12) | 0.0525 (14) | 0.0581 (13) | 0.0079 (11) | −0.0024 (10) | −0.0050 (11) |
C2 | 0.0474 (11) | 0.0627 (15) | 0.0551 (13) | 0.0012 (12) | 0.0041 (10) | 0.0131 (13) |
C3 | 0.0475 (12) | 0.0629 (15) | 0.0605 (14) | −0.0099 (12) | −0.0065 (10) | 0.0131 (13) |
C4 | 0.0585 (14) | 0.0724 (18) | 0.0523 (14) | −0.0051 (13) | −0.0119 (11) | −0.0023 (12) |
C5 | 0.0562 (12) | 0.0586 (15) | 0.0513 (13) | −0.0032 (12) | 0.0013 (10) | 0.0134 (12) |
C6 | 0.0692 (16) | 0.086 (2) | 0.0463 (13) | −0.0013 (15) | 0.0090 (11) | 0.0175 (14) |
C7 | 0.0580 (14) | 0.0792 (19) | 0.0405 (12) | −0.0064 (13) | 0.0073 (10) | 0.0008 (12) |
C8 | 0.0426 (10) | 0.0499 (12) | 0.0397 (10) | −0.0086 (9) | 0.0073 (8) | −0.0006 (9) |
C9 | 0.0373 (10) | 0.0421 (11) | 0.0379 (10) | −0.0075 (9) | 0.0030 (8) | −0.0013 (9) |
C10 | 0.0470 (11) | 0.0416 (11) | 0.0511 (12) | −0.0082 (10) | 0.0006 (9) | 0.0019 (10) |
C11 | 0.0411 (10) | 0.0617 (14) | 0.0395 (11) | −0.0005 (10) | 0.0030 (8) | −0.0068 (10) |
C12 | 0.0368 (10) | 0.0585 (13) | 0.0365 (10) | −0.0055 (10) | 0.0015 (8) | −0.0053 (10) |
C13 | 0.0347 (9) | 0.0468 (11) | 0.0437 (11) | −0.0072 (9) | 0.0053 (8) | −0.0039 (10) |
C14 | 0.0418 (10) | 0.0529 (13) | 0.0411 (11) | −0.0072 (9) | 0.0063 (8) | −0.0083 (9) |
C15 | 0.0514 (13) | 0.0799 (18) | 0.0547 (13) | 0.0008 (13) | 0.0146 (11) | −0.0118 (14) |
C16 | 0.0528 (13) | 0.0752 (19) | 0.0689 (16) | 0.0067 (13) | 0.0121 (11) | −0.0145 (14) |
C17 | 0.0396 (10) | 0.0485 (12) | 0.0571 (13) | −0.0040 (10) | 0.0055 (9) | −0.0023 (11) |
C18 | 0.0439 (11) | 0.0514 (13) | 0.0604 (14) | −0.0116 (10) | −0.0003 (10) | −0.0049 (11) |
C19 | 0.0667 (16) | 0.0411 (13) | 0.101 (2) | −0.0114 (13) | −0.0031 (15) | −0.0005 (14) |
C20 | 0.0369 (10) | 0.0568 (14) | 0.0644 (14) | −0.0021 (11) | 0.0021 (9) | 0.0054 (12) |
C21 | 0.0535 (13) | 0.095 (2) | 0.0601 (15) | 0.0012 (15) | −0.0010 (11) | 0.0096 (15) |
C22 | 0.0446 (12) | 0.0576 (15) | 0.097 (2) | −0.0032 (12) | 0.0006 (13) | 0.0140 (15) |
C23 | 0.0437 (12) | 0.0778 (19) | 0.091 (2) | 0.0027 (13) | 0.0058 (12) | 0.0347 (17) |
C24 | 0.0441 (11) | 0.0453 (12) | 0.0623 (13) | 0.0053 (10) | 0.0066 (10) | 0.0064 (12) |
O25 | 0.0504 (9) | 0.128 (2) | 0.0738 (12) | −0.0005 (12) | −0.0075 (8) | 0.0338 (14) |
O26 | 0.0403 (8) | 0.0772 (13) | 0.0627 (10) | −0.0043 (9) | 0.0080 (7) | 0.0201 (10) |
O27 | 0.0613 (10) | 0.0763 (14) | 0.0811 (13) | −0.0040 (11) | 0.0019 (9) | 0.0282 (12) |
O28 | 0.0431 (9) | 0.0865 (14) | 0.0676 (11) | −0.0015 (10) | 0.0038 (8) | 0.0170 (11) |
O29 | 0.0794 (13) | 0.0778 (14) | 0.0518 (10) | −0.0098 (11) | −0.0037 (9) | −0.0160 (9) |
Geometric parameters (Å, º) top
C1—C2 | 1.528 (3) | C13—C18 | 1.545 (3) |
C1—C10 | 1.534 (3) | C13—C14 | 1.565 (3) |
C1—H1A | 0.9700 | C14—C15 | 1.529 (3) |
C1—H1B | 0.9700 | C14—H14 | 0.9800 |
C2—C3 | 1.494 (3) | C15—C16 | 1.536 (4) |
C2—H2A | 0.9700 | C15—H15A | 0.9700 |
C2—H2B | 0.9700 | C15—H15B | 0.9700 |
C3—O25 | 1.218 (3) | C16—C17 | 1.563 (3) |
C3—C4 | 1.485 (4) | C16—H16A | 0.9700 |
C4—C5 | 1.544 (4) | C16—H16B | 0.9700 |
C4—H4A | 0.9700 | C17—C20 | 1.537 (3) |
C4—H4B | 0.9700 | C17—H17 | 0.9800 |
C5—C6 | 1.536 (4) | C18—H18A | 0.9600 |
C5—C10 | 1.547 (3) | C18—H18B | 0.9600 |
C5—H5 | 0.9800 | C18—H18C | 0.9600 |
C6—C7 | 1.532 (4) | C19—H19A | 0.9600 |
C6—H6A | 0.9700 | C19—H19B | 0.9600 |
C6—H6B | 0.9700 | C19—H19C | 0.9600 |
C7—O29 | 1.427 (4) | C20—C22 | 1.537 (4) |
C7—C8 | 1.533 (3) | C20—C21 | 1.540 (4) |
C7—H7 | 0.9800 | C20—H20 | 0.9800 |
C8—C14 | 1.521 (3) | C21—H21A | 0.9600 |
C8—C9 | 1.547 (3) | C21—H21B | 0.9600 |
C8—H8 | 0.9800 | C21—H21C | 0.9600 |
C9—C11 | 1.551 (3) | C22—C23 | 1.521 (4) |
C9—C10 | 1.555 (3) | C22—H22A | 0.9700 |
C9—H9 | 0.9800 | C22—H22B | 0.9700 |
C10—C19 | 1.543 (3) | C23—C24 | 1.493 (4) |
C11—C12 | 1.498 (3) | C23—H23A | 0.9700 |
C11—H11A | 0.9700 | C23—H23B | 0.9700 |
C11—H11B | 0.9700 | C24—O27 | 1.193 (3) |
C12—O26 | 1.217 (3) | C24—O28 | 1.328 (3) |
C12—C13 | 1.517 (3) | O28—H28 | 0.85 (4) |
C13—C17 | 1.543 (3) | O29—H29 | 0.99 (4) |
| | | |
C2—C1—C10 | 115.3 (2) | C12—C13—C14 | 100.71 (15) |
C2—C1—H1A | 108.5 | C17—C13—C14 | 101.80 (18) |
C10—C1—H1A | 108.5 | C18—C13—C14 | 112.15 (19) |
C2—C1—H1B | 108.5 | C8—C14—C15 | 118.0 (2) |
C10—C1—H1B | 108.5 | C8—C14—C13 | 112.94 (18) |
H1A—C1—H1B | 107.5 | C15—C14—C13 | 103.46 (17) |
C3—C2—C1 | 107.3 (2) | C8—C14—H14 | 107.3 |
C3—C2—H2A | 110.2 | C15—C14—H14 | 107.3 |
C1—C2—H2A | 110.2 | C13—C14—H14 | 107.3 |
C3—C2—H2B | 110.2 | C14—C15—C16 | 104.95 (19) |
C1—C2—H2B | 110.2 | C14—C15—H15A | 110.8 |
H2A—C2—H2B | 108.5 | C16—C15—H15A | 110.8 |
O25—C3—C4 | 123.5 (2) | C14—C15—H15B | 110.8 |
O25—C3—C2 | 122.4 (3) | C16—C15—H15B | 110.8 |
C4—C3—C2 | 114.0 (2) | H15A—C15—H15B | 108.8 |
C3—C4—C5 | 111.9 (2) | C15—C16—C17 | 107.50 (19) |
C3—C4—H4A | 109.2 | C15—C16—H16A | 110.2 |
C5—C4—H4A | 109.2 | C17—C16—H16A | 110.2 |
C3—C4—H4B | 109.2 | C15—C16—H16B | 110.2 |
C5—C4—H4B | 109.2 | C17—C16—H16B | 110.2 |
H4A—C4—H4B | 107.9 | H16A—C16—H16B | 108.5 |
C6—C5—C4 | 111.2 (2) | C20—C17—C13 | 118.0 (2) |
C6—C5—C10 | 113.0 (2) | C20—C17—C16 | 112.37 (18) |
C4—C5—C10 | 112.93 (19) | C13—C17—C16 | 103.5 (2) |
C6—C5—H5 | 106.4 | C20—C17—H17 | 107.5 |
C4—C5—H5 | 106.4 | C13—C17—H17 | 107.5 |
C10—C5—H5 | 106.4 | C16—C17—H17 | 107.5 |
C7—C6—C5 | 114.6 (2) | C13—C18—H18A | 109.5 |
C7—C6—H6A | 108.6 | C13—C18—H18B | 109.5 |
C5—C6—H6A | 108.6 | H18A—C18—H18B | 109.5 |
C7—C6—H6B | 108.6 | C13—C18—H18C | 109.5 |
C5—C6—H6B | 108.6 | H18A—C18—H18C | 109.5 |
H6A—C6—H6B | 107.6 | H18B—C18—H18C | 109.5 |
O29—C7—C6 | 113.2 (2) | C10—C19—H19A | 109.5 |
O29—C7—C8 | 108.0 (2) | C10—C19—H19B | 109.5 |
C6—C7—C8 | 110.3 (2) | H19A—C19—H19B | 109.5 |
O29—C7—H7 | 108.4 | C10—C19—H19C | 109.5 |
C6—C7—H7 | 108.4 | H19A—C19—H19C | 109.5 |
C8—C7—H7 | 108.4 | H19B—C19—H19C | 109.5 |
C14—C8—C7 | 113.20 (19) | C17—C20—C22 | 109.7 (2) |
C14—C8—C9 | 110.32 (17) | C17—C20—C21 | 112.64 (18) |
C7—C8—C9 | 109.69 (18) | C22—C20—C21 | 110.5 (2) |
C14—C8—H8 | 107.8 | C17—C20—H20 | 108.0 |
C7—C8—H8 | 107.8 | C22—C20—H20 | 108.0 |
C9—C8—H8 | 107.8 | C21—C20—H20 | 108.0 |
C8—C9—C11 | 113.10 (17) | C20—C21—H21A | 109.5 |
C8—C9—C10 | 111.15 (17) | C20—C21—H21B | 109.5 |
C11—C9—C10 | 113.25 (18) | H21A—C21—H21B | 109.5 |
C8—C9—H9 | 106.2 | C20—C21—H21C | 109.5 |
C11—C9—H9 | 106.2 | H21A—C21—H21C | 109.5 |
C10—C9—H9 | 106.2 | H21B—C21—H21C | 109.5 |
C1—C10—C19 | 105.4 (2) | C23—C22—C20 | 116.3 (3) |
C1—C10—C5 | 109.17 (18) | C23—C22—H22A | 108.2 |
C19—C10—C5 | 109.3 (2) | C20—C22—H22A | 108.2 |
C1—C10—C9 | 112.79 (19) | C23—C22—H22B | 108.2 |
C19—C10—C9 | 111.70 (18) | C20—C22—H22B | 108.2 |
C5—C10—C9 | 108.37 (19) | H22A—C22—H22B | 107.4 |
C12—C11—C9 | 113.22 (18) | C24—C23—C22 | 115.6 (2) |
C12—C11—H11A | 108.9 | C24—C23—H23A | 108.4 |
C9—C11—H11A | 108.9 | C22—C23—H23A | 108.4 |
C12—C11—H11B | 108.9 | C24—C23—H23B | 108.4 |
C9—C11—H11B | 108.9 | C22—C23—H23B | 108.4 |
H11A—C11—H11B | 107.7 | H23A—C23—H23B | 107.4 |
O26—C12—C11 | 121.67 (19) | O27—C24—O28 | 122.6 (2) |
O26—C12—C13 | 122.9 (2) | O27—C24—C23 | 125.5 (2) |
C11—C12—C13 | 115.11 (19) | O28—C24—C23 | 111.8 (2) |
C12—C13—C17 | 116.92 (19) | C24—O28—H28 | 109 (2) |
C12—C13—C18 | 112.11 (19) | C7—O29—H29 | 110 (3) |
C17—C13—C18 | 112.04 (16) | | |
Crystal data top
C24H36O5 | Dx = 1.197 Mg m−3 |
Mr = 404.53 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 3622 reflections |
a = 8.4953 (1) Å | θ = 4.0–30.0° |
b = 12.7060 (2) Å | µ = 0.08 mm−1 |
c = 20.8011 (3) Å | T = 295 K |
V = 2245.30 (5) Å3 | Prism, colourless |
Z = 4 | 0.45 × 0.35 × 0.32 mm |
F(000) = 880 | |
Data collection top
Nonius Kappa CCD diffractometer | 3189 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.035 |
Graphite monochromator | θmax = 30.0°, θmin = 4.0° |
ϕ scans and ω scans | h = −11→11 |
26164 measured reflections | k = −17→17 |
3664 independent reflections | l = −29→29 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.050 | All H-atom parameters refined |
wR(F2) = 0.146 | w = 1/[σ2(Fo2) + (0.0967P)2 + 0.2322P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.009 |
3664 reflections | Δρmax = 0.45 e Å−3 |
406 parameters | Δρmin = −0.32 e Å−3 |
0 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.3 (15) |
Crystal data top
C24H36O5 | V = 2245.30 (5) Å3 |
Mr = 404.53 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 8.4953 (1) Å | µ = 0.08 mm−1 |
b = 12.7060 (2) Å | T = 295 K |
c = 20.8011 (3) Å | 0.45 × 0.35 × 0.32 mm |
Data collection top
Nonius Kappa CCD diffractometer | 3189 reflections with I > 2σ(I) |
26164 measured reflections | Rint = 0.035 |
3664 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.050 | All H-atom parameters refined |
wR(F2) = 0.146 | Δρmax = 0.45 e Å−3 |
S = 1.06 | Δρmin = −0.32 e Å−3 |
3664 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
406 parameters | Absolute structure parameter: −0.3 (15) |
0 restraints | |
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 | x | y | z | Uiso*/Ueq | |
C1 | −0.0476 (3) | 0.0840 (2) | 0.09477 (11) | 0.0472 (5) | |
C2 | −0.2061 (3) | 0.1052 (2) | 0.12646 (13) | 0.0541 (6) | |
C3 | −0.2663 (3) | 0.2126 (3) | 0.10838 (12) | 0.0548 (6) | |
C4 | −0.1503 (3) | 0.2999 (2) | 0.11661 (13) | 0.0528 (6) | |
C5 | 0.0102 (3) | 0.2751 (2) | 0.08602 (10) | 0.0438 (5) | |
C6 | 0.1239 (3) | 0.3673 (2) | 0.09973 (13) | 0.0527 (6) | |
C7 | 0.1644 (3) | 0.36698 (17) | 0.17024 (11) | 0.0412 (4) | |
C8 | 0.2422 (2) | 0.26719 (15) | 0.19326 (9) | 0.0332 (4) | |
C9 | 0.1270 (2) | 0.17386 (15) | 0.17969 (8) | 0.0316 (3) | |
C10 | 0.0794 (2) | 0.16743 (18) | 0.10744 (9) | 0.0381 (4) | |
C11 | 0.1927 (3) | 0.06965 (15) | 0.20612 (9) | 0.0363 (4) | |
C12 | 0.2444 (2) | 0.07523 (14) | 0.27686 (8) | 0.0323 (4) | |
C13 | 0.3626 (2) | 0.16506 (13) | 0.28733 (8) | 0.0298 (3) | |
C14 | 0.2854 (2) | 0.26884 (14) | 0.26447 (8) | 0.0312 (4) | |
C15 | 0.3989 (3) | 0.35427 (16) | 0.28795 (12) | 0.0441 (5) | |
C16 | 0.4646 (3) | 0.31082 (17) | 0.35148 (12) | 0.0471 (5) | |
C17 | 0.4041 (2) | 0.19527 (14) | 0.35805 (9) | 0.0317 (4) | |
C18 | 0.5152 (3) | 0.14028 (19) | 0.25028 (11) | 0.0398 (4) | |
C19 | 0.2208 (3) | 0.1395 (3) | 0.06451 (11) | 0.0531 (6) | |
C20 | 0.5209 (3) | 0.12555 (16) | 0.39534 (10) | 0.0370 (4) | |
C21 | 0.4644 (4) | 0.01176 (18) | 0.40226 (11) | 0.0506 (6) | |
C22 | 0.5581 (3) | 0.1717 (2) | 0.46237 (10) | 0.0423 (5) | |
C23 | 0.4158 (3) | 0.1829 (3) | 0.50623 (11) | 0.0555 (6) | |
C24 | 0.4543 (4) | 0.2252 (3) | 0.57183 (13) | 0.0617 (7) | |
O25 | −0.3978 (2) | 0.2283 (3) | 0.08818 (13) | 0.0812 (8) | |
O26 | 0.1104 (2) | 0.09003 (13) | 0.31787 (7) | 0.0417 (3) | |
O27 | 0.4346 (7) | 0.1806 (3) | 0.62092 (13) | 0.1301 (18) | |
O28 | 0.5105 (3) | 0.32179 (19) | 0.56985 (11) | 0.0726 (6) | |
O29 | 0.1281 (3) | 0.43893 (13) | 0.20588 (9) | 0.0564 (5) | |
H1A | −0.016 (4) | 0.023 (2) | 0.1072 (14) | 0.047 (8)* | |
H1B | −0.064 (4) | 0.081 (3) | 0.0449 (16) | 0.065 (9)* | |
H2A | −0.189 (5) | 0.108 (3) | 0.1786 (19) | 0.076 (10)* | |
H2B | −0.288 (6) | 0.059 (3) | 0.113 (2) | 0.092 (13)* | |
H4A | −0.145 (4) | 0.312 (2) | 0.1636 (14) | 0.046 (7)* | |
H4B | −0.195 (5) | 0.366 (3) | 0.0975 (19) | 0.078 (11)* | |
H5 | 0.004 (3) | 0.2680 (19) | 0.0388 (11) | 0.034 (6)* | |
H6A | 0.230 (6) | 0.351 (4) | 0.072 (2) | 0.091 (13)* | |
H6B | 0.078 (5) | 0.433 (3) | 0.0840 (19) | 0.081 (11)* | |
H8 | 0.331 (3) | 0.258 (2) | 0.1710 (13) | 0.037 (6)* | |
H9 | 0.034 (4) | 0.187 (2) | 0.2040 (13) | 0.045 (7)* | |
H11A | 0.282 (4) | 0.047 (2) | 0.1781 (14) | 0.045 (7)* | |
H11B | 0.116 (4) | 0.017 (2) | 0.2000 (13) | 0.044 (7)* | |
H12 | 0.295 (3) | 0.010 (2) | 0.2884 (12) | 0.036 (6)* | |
H14 | 0.187 (3) | 0.2826 (19) | 0.2877 (11) | 0.030 (5)* | |
H15A | 0.488 (4) | 0.360 (2) | 0.2529 (15) | 0.049 (7)* | |
H15B | 0.347 (5) | 0.416 (3) | 0.2883 (17) | 0.073 (10)* | |
H16A | 0.429 (4) | 0.345 (3) | 0.3921 (16) | 0.058 (8)* | |
H16B | 0.585 (5) | 0.310 (3) | 0.3502 (17) | 0.076 (11)* | |
H17 | 0.309 (3) | 0.2094 (19) | 0.3817 (11) | 0.029 (5)* | |
H18A | 0.589 (4) | 0.192 (2) | 0.2587 (13) | 0.040 (6)* | |
H18B | 0.557 (4) | 0.080 (3) | 0.2612 (15) | 0.060 (9)* | |
H18C | 0.497 (4) | 0.132 (3) | 0.2011 (16) | 0.063 (9)* | |
H19A | 0.313 (5) | 0.178 (3) | 0.0743 (19) | 0.076 (11)* | |
H19B | 0.245 (4) | 0.073 (3) | 0.0677 (17) | 0.063 (10)* | |
H19C | 0.179 (5) | 0.147 (3) | 0.0209 (17) | 0.067 (9)* | |
H20 | 0.621 (3) | 0.132 (2) | 0.3723 (12) | 0.039 (6)* | |
H21A | 0.359 (4) | 0.011 (2) | 0.4173 (14) | 0.047 (7)* | |
H21B | 0.454 (4) | −0.023 (2) | 0.3597 (15) | 0.057 (8)* | |
H21C | 0.521 (5) | −0.033 (3) | 0.4342 (19) | 0.080 (11)* | |
H22A | 0.640 (3) | 0.125 (2) | 0.4790 (12) | 0.035 (6)* | |
H22B | 0.609 (5) | 0.233 (3) | 0.4546 (17) | 0.065 (9)* | |
H23A | 0.335 (5) | 0.234 (3) | 0.4856 (18) | 0.073 (11)* | |
H23B | 0.351 (10) | 0.117 (5) | 0.506 (3) | 0.15 (2)* | |
H26 | 0.031 (5) | 0.058 (3) | 0.3046 (19) | 0.078 (11)* | |
H28 | 0.545 (5) | 0.330 (3) | 0.615 (2) | 0.077 (11)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0431 (11) | 0.0597 (14) | 0.0389 (10) | −0.0059 (11) | −0.0065 (9) | −0.0069 (10) |
C2 | 0.0426 (12) | 0.0700 (16) | 0.0497 (12) | −0.0132 (12) | −0.0016 (10) | 0.0047 (11) |
C3 | 0.0345 (11) | 0.0832 (18) | 0.0466 (11) | −0.0005 (12) | 0.0014 (9) | 0.0114 (12) |
C4 | 0.0405 (11) | 0.0628 (15) | 0.0552 (13) | 0.0078 (11) | −0.0063 (10) | 0.0060 (11) |
C5 | 0.0385 (10) | 0.0585 (12) | 0.0345 (9) | −0.0010 (10) | −0.0042 (8) | 0.0085 (8) |
C6 | 0.0518 (13) | 0.0568 (14) | 0.0494 (12) | −0.0081 (11) | −0.0107 (11) | 0.0209 (11) |
C7 | 0.0370 (9) | 0.0396 (10) | 0.0470 (10) | −0.0024 (8) | −0.0059 (8) | 0.0107 (8) |
C8 | 0.0327 (9) | 0.0334 (8) | 0.0336 (8) | 0.0018 (7) | −0.0007 (7) | 0.0020 (7) |
C9 | 0.0321 (8) | 0.0356 (8) | 0.0271 (7) | −0.0003 (7) | 0.0015 (7) | −0.0025 (6) |
C10 | 0.0341 (9) | 0.0528 (11) | 0.0274 (7) | 0.0001 (8) | 0.0009 (7) | −0.0013 (8) |
C11 | 0.0452 (10) | 0.0321 (8) | 0.0317 (8) | 0.0003 (8) | −0.0038 (8) | −0.0065 (7) |
C12 | 0.0408 (9) | 0.0262 (8) | 0.0300 (7) | −0.0013 (7) | −0.0007 (7) | −0.0032 (6) |
C13 | 0.0333 (8) | 0.0259 (7) | 0.0303 (7) | 0.0024 (6) | −0.0007 (7) | −0.0019 (6) |
C14 | 0.0333 (9) | 0.0261 (7) | 0.0342 (8) | 0.0006 (7) | −0.0030 (7) | −0.0021 (6) |
C15 | 0.0518 (12) | 0.0273 (8) | 0.0531 (11) | −0.0052 (8) | −0.0105 (11) | 0.0009 (8) |
C16 | 0.0539 (13) | 0.0335 (9) | 0.0540 (12) | −0.0089 (9) | −0.0158 (11) | −0.0024 (9) |
C17 | 0.0324 (9) | 0.0286 (8) | 0.0342 (8) | 0.0020 (7) | −0.0048 (7) | −0.0039 (6) |
C18 | 0.0353 (10) | 0.0420 (10) | 0.0420 (9) | 0.0079 (9) | 0.0047 (8) | −0.0022 (8) |
C19 | 0.0426 (12) | 0.0830 (19) | 0.0337 (9) | 0.0034 (13) | 0.0064 (9) | −0.0115 (11) |
C20 | 0.0358 (9) | 0.0402 (10) | 0.0349 (8) | 0.0063 (8) | −0.0044 (8) | −0.0021 (7) |
C21 | 0.0720 (18) | 0.0387 (10) | 0.0413 (10) | 0.0065 (11) | −0.0145 (12) | 0.0003 (9) |
C22 | 0.0352 (10) | 0.0502 (12) | 0.0415 (10) | 0.0032 (9) | −0.0115 (8) | −0.0061 (9) |
C23 | 0.0443 (12) | 0.0807 (18) | 0.0414 (11) | 0.0043 (13) | −0.0078 (10) | −0.0198 (12) |
C24 | 0.0687 (17) | 0.0679 (16) | 0.0484 (12) | 0.0124 (15) | −0.0148 (13) | −0.0142 (11) |
O25 | 0.0368 (9) | 0.119 (2) | 0.0877 (15) | −0.0061 (12) | −0.0120 (10) | 0.0315 (15) |
O26 | 0.0439 (8) | 0.0446 (8) | 0.0367 (6) | −0.0153 (7) | 0.0049 (6) | −0.0086 (6) |
O27 | 0.237 (5) | 0.098 (2) | 0.0557 (13) | −0.031 (3) | −0.033 (2) | −0.0001 (13) |
O28 | 0.0904 (17) | 0.0728 (13) | 0.0546 (10) | −0.0029 (13) | −0.0162 (11) | −0.0093 (9) |
O29 | 0.0647 (11) | 0.0397 (8) | 0.0649 (10) | 0.0153 (8) | −0.0139 (9) | 0.0029 (7) |
Geometric parameters (Å, º) top
C1—C2 | 1.523 (4) | C13—C14 | 1.547 (2) |
C1—C10 | 1.536 (3) | C13—C17 | 1.561 (2) |
C1—H1A | 0.86 (3) | C14—C15 | 1.532 (3) |
C1—H1B | 1.05 (3) | C14—H14 | 0.98 (3) |
C2—C3 | 1.505 (4) | C15—C16 | 1.537 (3) |
C2—H2A | 1.09 (4) | C15—H15A | 1.06 (3) |
C2—H2B | 0.95 (5) | C15—H15B | 0.90 (4) |
C3—O25 | 1.210 (3) | C16—C17 | 1.561 (3) |
C3—C4 | 1.493 (4) | C16—H16A | 0.99 (3) |
C4—C5 | 1.538 (3) | C16—H16B | 1.02 (4) |
C4—H4A | 0.99 (3) | C17—C20 | 1.540 (3) |
C4—H4B | 1.00 (4) | C17—H17 | 0.96 (2) |
C5—C6 | 1.545 (4) | C18—H18A | 0.92 (3) |
C5—C10 | 1.554 (3) | C18—H18B | 0.88 (4) |
C5—H5 | 0.99 (2) | C18—H18C | 1.04 (3) |
C6—C7 | 1.507 (3) | C19—H19A | 0.95 (5) |
C6—H6A | 1.09 (5) | C19—H19B | 0.87 (4) |
C6—H6B | 0.98 (4) | C19—H19C | 0.98 (4) |
C7—O29 | 1.217 (3) | C20—C21 | 1.530 (3) |
C7—C8 | 1.508 (3) | C20—C22 | 1.545 (3) |
C8—C14 | 1.526 (2) | C20—H20 | 0.98 (3) |
C8—C9 | 1.563 (3) | C21—H21A | 0.95 (3) |
C8—H8 | 0.89 (3) | C21—H21B | 0.99 (3) |
C9—C11 | 1.538 (3) | C21—H21C | 1.00 (4) |
C9—C10 | 1.559 (2) | C22—C23 | 1.522 (4) |
C9—H9 | 0.96 (3) | C22—H22A | 0.98 (3) |
C10—C19 | 1.538 (3) | C22—H22B | 0.90 (4) |
C11—C12 | 1.537 (2) | C23—C24 | 1.503 (3) |
C11—H11A | 1.00 (3) | C23—H23A | 1.03 (4) |
C11—H11B | 0.94 (3) | C23—H23B | 1.00 (7) |
C12—O26 | 1.435 (3) | C24—O27 | 1.180 (4) |
C12—C13 | 1.536 (3) | C24—O28 | 1.317 (4) |
C12—H12 | 0.96 (3) | O26—H26 | 0.84 (4) |
C13—C18 | 1.541 (3) | O28—H28 | 0.98 (4) |
| | | |
C2—C1—C10 | 115.2 (2) | C12—C13—C17 | 117.67 (15) |
C2—C1—H1A | 108 (2) | C18—C13—C17 | 109.35 (16) |
C10—C1—H1A | 110 (2) | C14—C13—C17 | 100.12 (13) |
C2—C1—H1B | 109 (2) | C8—C14—C15 | 118.07 (17) |
C10—C1—H1B | 107 (2) | C8—C14—C13 | 112.85 (14) |
H1A—C1—H1B | 108 (3) | C15—C14—C13 | 103.85 (15) |
C3—C2—C1 | 110.6 (2) | C8—C14—H14 | 106.1 (14) |
C3—C2—H2A | 105 (2) | C15—C14—H14 | 104.6 (14) |
C1—C2—H2A | 109 (2) | C13—C14—H14 | 111.1 (14) |
C3—C2—H2B | 104 (3) | C14—C15—C16 | 104.37 (16) |
C1—C2—H2B | 115 (3) | C14—C15—H15A | 106.5 (17) |
H2A—C2—H2B | 113 (4) | C16—C15—H15A | 110.9 (17) |
O25—C3—C4 | 121.7 (3) | C14—C15—H15B | 108 (3) |
O25—C3—C2 | 123.4 (3) | C16—C15—H15B | 119 (2) |
C4—C3—C2 | 114.9 (2) | H15A—C15—H15B | 107 (3) |
C3—C4—C5 | 112.7 (2) | C15—C16—C17 | 107.06 (16) |
C3—C4—H4A | 104.8 (17) | C15—C16—H16A | 118 (2) |
C5—C4—H4A | 113.5 (18) | C17—C16—H16A | 103.5 (19) |
C3—C4—H4B | 109 (2) | C15—C16—H16B | 110 (2) |
C5—C4—H4B | 110 (2) | C17—C16—H16B | 109 (2) |
H4A—C4—H4B | 106 (3) | H16A—C16—H16B | 109 (3) |
C4—C5—C6 | 108.8 (2) | C20—C17—C13 | 118.62 (15) |
C4—C5—C10 | 113.39 (19) | C20—C17—C16 | 111.89 (16) |
C6—C5—C10 | 112.23 (18) | C13—C17—C16 | 102.91 (15) |
C4—C5—H5 | 112.5 (15) | C20—C17—H17 | 113.0 (14) |
C6—C5—H5 | 106.6 (15) | C13—C17—H17 | 109.7 (14) |
C10—C5—H5 | 103.0 (14) | C16—C17—H17 | 98.4 (14) |
C7—C6—C5 | 108.70 (19) | C13—C18—H18A | 109.1 (17) |
C7—C6—H6A | 109 (2) | C13—C18—H18B | 113 (2) |
C5—C6—H6A | 106 (2) | H18A—C18—H18B | 107 (3) |
C7—C6—H6B | 115 (2) | C13—C18—H18C | 113 (2) |
C5—C6—H6B | 110 (3) | H18A—C18—H18C | 111 (3) |
H6A—C6—H6B | 108 (3) | H18B—C18—H18C | 103 (3) |
O29—C7—C6 | 122.2 (2) | C10—C19—H19A | 114 (2) |
O29—C7—C8 | 123.3 (2) | C10—C19—H19B | 111 (3) |
C6—C7—C8 | 114.3 (2) | H19A—C19—H19B | 107 (4) |
C7—C8—C14 | 113.70 (17) | C10—C19—H19C | 103 (2) |
C7—C8—C9 | 107.83 (15) | H19A—C19—H19C | 117 (3) |
C14—C8—C9 | 109.64 (15) | H19B—C19—H19C | 104 (3) |
C7—C8—H8 | 108.3 (17) | C21—C20—C17 | 112.88 (18) |
C14—C8—H8 | 107.7 (17) | C21—C20—C22 | 109.74 (18) |
C9—C8—H8 | 109.7 (17) | C17—C20—C22 | 111.60 (16) |
C11—C9—C10 | 113.18 (15) | C21—C20—H20 | 113.5 (16) |
C11—C9—C8 | 111.18 (15) | C17—C20—H20 | 105.2 (15) |
C10—C9—C8 | 112.10 (15) | C22—C20—H20 | 103.4 (16) |
C11—C9—H9 | 105.2 (17) | C20—C21—H21A | 109.8 (18) |
C10—C9—H9 | 107.7 (17) | C20—C21—H21B | 111.1 (19) |
C8—C9—H9 | 107.0 (16) | H21A—C21—H21B | 102 (3) |
C1—C10—C19 | 106.9 (2) | C20—C21—H21C | 117 (2) |
C1—C10—C5 | 107.00 (19) | H21A—C21—H21C | 103 (3) |
C19—C10—C5 | 109.4 (2) | H21B—C21—H21C | 113 (3) |
C1—C10—C9 | 112.58 (17) | C23—C22—C20 | 114.44 (18) |
C19—C10—C9 | 111.68 (17) | C23—C22—H22A | 114.3 (15) |
C5—C10—C9 | 109.17 (17) | C20—C22—H22A | 103.5 (15) |
C12—C11—C9 | 113.96 (15) | C23—C22—H22B | 114 (2) |
C12—C11—H11A | 110.7 (16) | C20—C22—H22B | 105 (2) |
C9—C11—H11A | 108.6 (16) | H22A—C22—H22B | 104 (3) |
C12—C11—H11B | 111.1 (16) | C24—C23—C22 | 113.9 (2) |
C9—C11—H11B | 108.3 (17) | C24—C23—H23A | 107 (2) |
H11A—C11—H11B | 104 (2) | C22—C23—H23A | 110 (2) |
O26—C12—C13 | 109.68 (14) | C24—C23—H23B | 115 (3) |
O26—C12—C11 | 110.40 (17) | C22—C23—H23B | 111 (4) |
C13—C12—C11 | 110.90 (15) | H23A—C23—H23B | 99 (5) |
O26—C12—H12 | 108.6 (15) | O27—C24—O28 | 121.7 (3) |
C13—C12—H12 | 108.2 (16) | O27—C24—C23 | 125.6 (3) |
C11—C12—H12 | 109.0 (15) | O28—C24—C23 | 112.6 (3) |
C12—C13—C18 | 109.11 (15) | C12—O26—H26 | 112 (3) |
C12—C13—C14 | 108.24 (15) | C24—O28—H28 | 101 (2) |
C18—C13—C14 | 112.13 (16) | | |
Crystal data top
C24H36O5·1/2(H2O) | F(000) = 1800 |
Mr = 413.54 | Dx = 1.172 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71070 Å |
a = 26.6049 (4) Å | Cell parameters from 5260 reflections |
b = 7.7044 (1) Å | θ = 4.2–27.5° |
c = 22.9126 (3) Å | µ = 0.08 mm−1 |
β = 93.424 (1)° | T = 295 K |
V = 4688.1 (1) Å3 | Irregular, colourless |
Z = 8 | 0.35 × 0.12 × 0.08 mm |
Data collection top
Nonius Kappa CCD diffractometer | 4381 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.034 |
Graphite monochromator | θmax = 27.5°, θmin = 4.2° |
ϕ scans and ω scans | h = −33→34 |
26846 measured reflections | k = −9→8 |
5683 independent reflections | l = −29→29 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.055 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.166 | w = 1/[σ2(Fo2) + (0.1005P)2 + 1.4815P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.004 |
5683 reflections | Δρmax = 0.35 e Å−3 |
567 parameters | Δρmin = −0.27 e Å−3 |
0 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 1.6 (15) |
Crystal data top
C24H36O5·1/2(H2O) | V = 4688.1 (1) Å3 |
Mr = 413.54 | Z = 8 |
Monoclinic, C2 | Mo Kα radiation |
a = 26.6049 (4) Å | µ = 0.08 mm−1 |
b = 7.7044 (1) Å | T = 295 K |
c = 22.9126 (3) Å | 0.35 × 0.12 × 0.08 mm |
β = 93.424 (1)° | |
Data collection top
Nonius Kappa CCD diffractometer | 4381 reflections with I > 2σ(I) |
26846 measured reflections | Rint = 0.034 |
5683 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.055 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.166 | Δρmax = 0.35 e Å−3 |
S = 1.01 | Δρmin = −0.27 e Å−3 |
5683 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
567 parameters | Absolute structure parameter: 1.6 (15) |
0 restraints | |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O25A | 0.71735 (10) | 0.8309 (6) | 0.54387 (13) | 0.0830 (8) | |
O29A | 0.87669 (12) | 1.2413 (5) | 0.67907 (14) | 0.0822 (8) | |
O26A | 0.90450 (9) | 0.5944 (5) | 0.71548 (10) | 0.0573 (6) | |
H26A | 0.8893 (14) | 0.509 (6) | 0.7055 (16) | 0.055 (10)* | |
O27A | 1.17998 (13) | 0.7213 (8) | 0.8870 (2) | 0.1363 (18) | |
O28A | 1.12331 (11) | 0.9015 (6) | 0.84937 (15) | 0.0887 (9) | |
H28A | 1.1560 (18) | 0.987 (7) | 0.8418 (19) | 0.090 (14)* | |
C1A | 0.84182 (14) | 0.7208 (7) | 0.52203 (14) | 0.0645 (9) | |
H11 | 0.8315 | 0.7471 | 0.4817 | 0.077* | |
H12 | 0.8634 | 0.6193 | 0.5221 | 0.077* | |
C2A | 0.79504 (14) | 0.6771 (6) | 0.55480 (14) | 0.0616 (8) | |
H21 | 0.7765 | 0.5839 | 0.5349 | 0.074* | |
H22 | 0.8050 | 0.6383 | 0.5941 | 0.074* | |
C3A | 0.76230 (14) | 0.8342 (6) | 0.55755 (14) | 0.0609 (8) | |
C4A | 0.78788 (14) | 0.9980 (6) | 0.57845 (15) | 0.0629 (8) | |
H41 | 0.7953 | 0.9900 | 0.6203 | 0.075* | |
H42 | 0.7650 | 1.0947 | 0.5713 | 0.075* | |
C5A | 0.83735 (15) | 1.0350 (6) | 0.54837 (16) | 0.0661 (9) | |
H5A | 0.8282 | 1.0650 | 0.5075 | 0.079* | |
C6A | 0.86248 (17) | 1.1946 (7) | 0.5771 (2) | 0.0791 (11) | |
H61 | 0.8882 | 1.2374 | 0.5524 | 0.095* | |
H62 | 0.8375 | 1.2854 | 0.5803 | 0.095* | |
C7A | 0.88624 (14) | 1.1545 (6) | 0.63717 (18) | 0.0648 (9) | |
C8A | 0.92068 (12) | 0.9967 (6) | 0.64061 (15) | 0.0550 (7) | |
H8A | 0.9499 | 1.0227 | 0.6181 | 0.066* | |
C9A | 0.89325 (12) | 0.8367 (6) | 0.61178 (13) | 0.0504 (7) | |
H9A | 0.8638 | 0.8147 | 0.6345 | 0.060* | |
C10A | 0.87253 (13) | 0.8750 (6) | 0.54801 (14) | 0.0602 (8) | |
C11A | 0.92572 (13) | 0.6740 (6) | 0.61732 (13) | 0.0555 (7) | |
H111 | 0.9543 | 0.6878 | 0.5933 | 0.067* | |
H112 | 0.9062 | 0.5759 | 0.6022 | 0.067* | |
C12A | 0.94521 (11) | 0.6337 (5) | 0.68030 (13) | 0.0497 (7) | |
H12A | 0.9678 | 0.5332 | 0.6799 | 0.060* | |
C13A | 0.97458 (11) | 0.7899 (6) | 0.70680 (13) | 0.0507 (7) | |
C14A | 0.93992 (12) | 0.9514 (6) | 0.70249 (14) | 0.0520 (7) | |
H14A | 0.9103 | 0.9240 | 0.7242 | 0.062* | |
C15A | 0.97004 (13) | 1.0877 (6) | 0.73818 (17) | 0.0652 (9) | |
H151 | 0.9480 | 1.1749 | 0.7533 | 0.078* | |
H152 | 0.9944 | 1.1444 | 0.7147 | 0.078* | |
C16A | 0.99655 (14) | 0.9827 (7) | 0.78814 (18) | 0.0704 (10) | |
H161 | 0.9826 | 1.0116 | 0.8251 | 0.084* | |
H162 | 1.0323 | 1.0089 | 0.7911 | 0.084* | |
C17A | 0.98808 (12) | 0.7875 (6) | 0.77406 (14) | 0.0553 (8) | |
H17A | 0.9578 | 0.7510 | 0.7932 | 0.066* | |
C18A | 1.02287 (13) | 0.8153 (7) | 0.67385 (16) | 0.0645 (9) | |
H181 | 1.0142 | 0.8606 | 0.6355 | 0.077* | |
H182 | 1.0397 | 0.7057 | 0.6705 | 0.077* | |
H183 | 1.0448 | 0.8953 | 0.6950 | 0.077* | |
C19A | 0.91518 (18) | 0.9088 (9) | 0.50690 (18) | 0.0894 (14) | |
H191 | 0.9333 | 0.8030 | 0.5012 | 0.107* | |
H192 | 0.9377 | 0.9947 | 0.5239 | 0.107* | |
H193 | 0.9011 | 0.9500 | 0.4699 | 0.107* | |
C20A | 1.03174 (13) | 0.6706 (6) | 0.79757 (16) | 0.0620 (9) | |
H20A | 1.0622 | 0.7058 | 0.7787 | 0.074* | |
C21A | 1.02227 (16) | 0.4806 (7) | 0.7841 (2) | 0.0789 (11) | |
H211 | 0.9890 | 0.4499 | 0.7944 | 0.095* | |
H212 | 1.0465 | 0.4111 | 0.8062 | 0.095* | |
H213 | 1.0253 | 0.4605 | 0.7431 | 0.095* | |
C22A | 1.04146 (14) | 0.6943 (8) | 0.86397 (16) | 0.0765 (12) | |
H221 | 1.0372 | 0.8158 | 0.8736 | 0.092* | |
H222 | 1.0166 | 0.6284 | 0.8839 | 0.092* | |
C23A | 1.09407 (15) | 0.6360 (8) | 0.88655 (19) | 0.0856 (13) | |
H231 | 1.0937 | 0.6200 | 0.9285 | 0.103* | |
H232 | 1.1006 | 0.5235 | 0.8696 | 0.103* | |
C24A | 1.13695 (15) | 0.7526 (8) | 0.87483 (16) | 0.0767 (12) | |
O25B | 0.81557 (13) | 0.1645 (6) | 1.03524 (10) | 0.0935 (10) | |
O29B | 0.78136 (12) | 0.1223 (5) | 0.78345 (13) | 0.0834 (9) | |
O26B | 0.68402 (8) | 0.6650 | 0.84201 (10) | 0.0597 (6) | |
H26B | 0.6839 (17) | 0.698 (7) | 0.876 (2) | 0.087 (14)* | |
O27B | 0.5588 (3) | 0.907 (2) | 0.5041 (5) | 0.080 (4) | 0.50 |
O28B | 0.5156 (6) | 0.842 (3) | 0.5780 (6) | 0.108 (7) | 0.50 |
O27C | 0.5576 (10) | 0.844 (6) | 0.5087 (11) | 0.147 (14) | 0.30 |
O28C | 0.5165 (10) | 0.912 (6) | 0.5778 (10) | 0.147 (16) | 0.30 |
O27D | 0.5345 (8) | 0.7518 (19) | 0.5468 (11) | 0.072 (4) | 0.20 |
O28D | 0.5377 (8) | 1.033 (2) | 0.5364 (11) | 0.089 (6) | 0.20 |
C1B | 0.83391 (14) | 0.5449 (7) | 0.95892 (13) | 0.0662 (9) | |
H13 | 0.8666 | 0.5385 | 0.9801 | 0.079* | |
H14 | 0.8236 | 0.6657 | 0.9581 | 0.079* | |
C2B | 0.79614 (16) | 0.4410 (7) | 0.99243 (14) | 0.0710 (10) | |
H23 | 0.7966 | 0.4813 | 1.0326 | 0.085* | |
H24 | 0.7625 | 0.4584 | 0.9748 | 0.085* | |
C3B | 0.80917 (14) | 0.2522 (7) | 0.99136 (14) | 0.0661 (10) | |
C4B | 0.81642 (14) | 0.1795 (6) | 0.93172 (13) | 0.0631 (9) | |
H43 | 0.7841 | 0.1747 | 0.9098 | 0.076* | |
H44 | 0.8292 | 0.0618 | 0.9356 | 0.076* | |
C5B | 0.85316 (13) | 0.2885 (6) | 0.89765 (13) | 0.0570 (8) | |
H5B | 0.8865 | 0.2780 | 0.9180 | 0.068* | |
C6B | 0.85692 (14) | 0.2117 (7) | 0.83611 (14) | 0.0651 (9) | |
H63 | 0.8841 | 0.2670 | 0.8168 | 0.078* | |
H64 | 0.8639 | 0.0883 | 0.8388 | 0.078* | |
C7B | 0.80769 (14) | 0.2416 (6) | 0.80140 (13) | 0.0584 (8) | |
C8B | 0.79308 (12) | 0.4295 (6) | 0.79423 (12) | 0.0476 (7) | |
H8B | 0.8194 | 0.4891 | 0.7737 | 0.057* | |
C9B | 0.79078 (11) | 0.5117 (6) | 0.85616 (11) | 0.0458 (6) | |
H9B | 0.7638 | 0.4515 | 0.8753 | 0.055* | |
C10B | 0.83964 (12) | 0.4836 (6) | 0.89541 (13) | 0.0547 (8) | |
C11B | 0.77493 (11) | 0.7039 (6) | 0.85085 (13) | 0.0493 (7)* | |
H113 | 0.7709 | 0.7494 | 0.8897 | 0.059* | |
H114 | 0.8018 | 0.7686 | 0.8341 | 0.059* | |
C12B | 0.72641 (11) | 0.7350 (6) | 0.81368 (11) | 0.0476 (6) | |
H12B | 0.7216 | 0.8603 | 0.8088 | 0.057* | |
C13B | 0.72889 (11) | 0.6514 (5) | 0.75274 (11) | 0.0454 (6) | |
C14B | 0.74245 (12) | 0.4579 (5) | 0.75987 (12) | 0.0472 (7) | |
H14B | 0.7164 | 0.4042 | 0.7824 | 0.057* | |
C15B | 0.73579 (12) | 0.3880 (6) | 0.69761 (14) | 0.0580 (8)* | |
H153 | 0.7292 | 0.2642 | 0.6976 | 0.070* | |
H154 | 0.7655 | 0.4103 | 0.6762 | 0.070* | |
C16B | 0.68977 (14) | 0.4896 (6) | 0.67085 (14) | 0.0615 (8) | |
H163 | 0.6608 | 0.4136 | 0.6658 | 0.074* | |
H164 | 0.6971 | 0.5365 | 0.6330 | 0.074* | |
C17B | 0.67878 (12) | 0.6396 (6) | 0.71401 (12) | 0.0504 (7) | |
H17B | 0.6526 | 0.5988 | 0.7390 | 0.061* | |
C18B | 0.76843 (11) | 0.7501 (6) | 0.71953 (13) | 0.0514 (7)* | |
H184 | 0.8014 | 0.7271 | 0.7373 | 0.062* | |
H185 | 0.7617 | 0.8724 | 0.7210 | 0.062* | |
H186 | 0.7670 | 0.7125 | 0.6795 | 0.062* | |
C19B | 0.88391 (13) | 0.5870 (8) | 0.87227 (18) | 0.0772 (11) | |
H194 | 0.8780 | 0.7090 | 0.8770 | 0.093* | |
H195 | 0.8867 | 0.5615 | 0.8316 | 0.093* | |
H196 | 0.9146 | 0.5549 | 0.8938 | 0.093* | |
C20B | 0.65890 (12) | 0.8047 (6) | 0.68308 (13) | 0.0544 (7) | |
H20B | 0.6848 | 0.8428 | 0.6572 | 0.065* | |
C21B | 0.65027 (16) | 0.9546 (7) | 0.72504 (18) | 0.0756 (11) | |
H214 | 0.6368 | 1.0524 | 0.7034 | 0.091* | |
H215 | 0.6817 | 0.9864 | 0.7450 | 0.091* | |
H216 | 0.6269 | 0.9190 | 0.7531 | 0.091* | |
C22B | 0.61068 (13) | 0.7674 (6) | 0.64388 (14) | 0.0613 (8) | |
H223 | 0.6141 | 0.6566 | 0.6244 | 0.074* | |
H224 | 0.5820 | 0.7599 | 0.6680 | 0.074* | |
C23B | 0.60136 (13) | 0.9091 (7) | 0.59837 (16) | 0.0681 (10) | |
H233 | 0.5982 | 1.0188 | 0.6186 | 0.082* | |
H234 | 0.6308 | 0.9171 | 0.5754 | 0.082* | |
C24B | 0.55608 (13) | 0.8864 (6) | 0.55739 (14) | 0.0571 (8) | |
O1 | 0.4479 (8) | 0.672 (4) | 0.0573 (9) | 0.361 (10)* | 0.70 |
O2 | 0.5000 | 0.909 (5) | 0.0000 | 0.325 (14)* | 0.60 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O25A | 0.0679 (15) | 0.094 (2) | 0.0856 (17) | −0.0018 (16) | −0.0080 (12) | −0.0032 (17) |
O29A | 0.0932 (19) | 0.0527 (14) | 0.099 (2) | 0.0052 (14) | −0.0075 (15) | −0.0146 (15) |
O26A | 0.0587 (12) | 0.0521 (13) | 0.0604 (13) | −0.0151 (12) | −0.0024 (10) | −0.0048 (11) |
O27A | 0.0689 (19) | 0.149 (4) | 0.187 (4) | −0.010 (2) | −0.021 (2) | 0.080 (4) |
O28A | 0.0669 (16) | 0.085 (2) | 0.111 (2) | −0.0206 (16) | −0.0203 (15) | 0.0204 (19) |
C1A | 0.078 (2) | 0.072 (2) | 0.0424 (15) | 0.0096 (19) | −0.0069 (14) | −0.0061 (16) |
C2A | 0.075 (2) | 0.059 (2) | 0.0498 (16) | −0.0042 (18) | −0.0112 (14) | −0.0072 (16) |
C3A | 0.069 (2) | 0.067 (2) | 0.0457 (15) | 0.0003 (18) | −0.0035 (13) | 0.0016 (16) |
C4A | 0.072 (2) | 0.057 (2) | 0.0586 (18) | 0.0088 (17) | −0.0070 (15) | 0.0015 (16) |
C5A | 0.082 (2) | 0.060 (2) | 0.0553 (18) | 0.0010 (19) | −0.0048 (16) | 0.0150 (17) |
C6A | 0.088 (3) | 0.053 (2) | 0.094 (3) | −0.003 (2) | −0.006 (2) | 0.020 (2) |
C7A | 0.067 (2) | 0.0454 (18) | 0.081 (2) | −0.0097 (16) | −0.0022 (17) | 0.0031 (19) |
C8A | 0.0543 (17) | 0.0470 (17) | 0.0636 (18) | −0.0076 (14) | 0.0026 (13) | 0.0012 (15) |
C9A | 0.0566 (16) | 0.0453 (16) | 0.0489 (15) | −0.0035 (14) | 0.0014 (12) | −0.0036 (13) |
C10A | 0.0687 (19) | 0.064 (2) | 0.0480 (15) | 0.0006 (18) | 0.0048 (14) | 0.0065 (16) |
C11A | 0.0598 (17) | 0.0541 (18) | 0.0515 (16) | −0.0007 (15) | −0.0049 (13) | −0.0091 (15) |
C12A | 0.0519 (15) | 0.0423 (16) | 0.0544 (16) | −0.0039 (13) | −0.0026 (12) | −0.0057 (14) |
C13A | 0.0440 (14) | 0.0526 (18) | 0.0552 (16) | −0.0079 (13) | −0.0008 (12) | −0.0077 (14) |
C14A | 0.0519 (16) | 0.0452 (16) | 0.0585 (17) | −0.0075 (14) | −0.0003 (13) | −0.0056 (14) |
C15A | 0.0619 (19) | 0.057 (2) | 0.076 (2) | −0.0107 (17) | −0.0015 (16) | −0.0156 (18) |
C16A | 0.062 (2) | 0.070 (2) | 0.077 (2) | −0.0123 (19) | −0.0089 (17) | −0.022 (2) |
C17A | 0.0483 (15) | 0.063 (2) | 0.0544 (16) | −0.0133 (15) | −0.0029 (12) | −0.0083 (15) |
C18A | 0.0549 (17) | 0.069 (2) | 0.070 (2) | −0.0054 (17) | 0.0091 (14) | −0.0024 (18) |
C19A | 0.097 (3) | 0.114 (4) | 0.060 (2) | 0.000 (3) | 0.0176 (19) | 0.017 (2) |
C20A | 0.0522 (17) | 0.065 (2) | 0.0678 (19) | −0.0128 (17) | −0.0097 (14) | −0.0011 (18) |
C21A | 0.073 (2) | 0.064 (2) | 0.097 (3) | −0.008 (2) | −0.019 (2) | 0.004 (2) |
C22A | 0.066 (2) | 0.094 (3) | 0.068 (2) | −0.027 (2) | −0.0110 (16) | 0.010 (2) |
C23A | 0.083 (3) | 0.094 (3) | 0.076 (2) | −0.024 (2) | −0.0242 (19) | 0.022 (2) |
C24A | 0.067 (2) | 0.100 (3) | 0.0610 (19) | −0.016 (2) | −0.0180 (16) | 0.011 (2) |
O25B | 0.124 (2) | 0.111 (3) | 0.0462 (12) | 0.006 (2) | 0.0100 (13) | 0.0242 (16) |
O29B | 0.118 (2) | 0.0484 (15) | 0.0805 (17) | −0.0013 (16) | −0.0200 (16) | −0.0053 (13) |
O26B | 0.0638 (13) | 0.0738 (16) | 0.0421 (11) | −0.0141 (12) | 0.0073 (9) | −0.0101 (12) |
O27B | 0.041 (3) | 0.148 (10) | 0.052 (5) | −0.011 (5) | −0.002 (3) | 0.024 (6) |
O28B | 0.067 (7) | 0.188 (15) | 0.069 (9) | −0.035 (8) | −0.004 (6) | 0.064 (11) |
O27C | 0.124 (16) | 0.24 (3) | 0.075 (14) | 0.072 (18) | 0.012 (11) | −0.079 (18) |
O28C | 0.065 (12) | 0.30 (4) | 0.070 (15) | 0.043 (18) | −0.009 (10) | −0.08 (2) |
O27D | 0.081 (10) | 0.051 (8) | 0.079 (11) | 0.013 (7) | −0.025 (9) | −0.015 (8) |
O28D | 0.087 (11) | 0.064 (9) | 0.109 (13) | −0.012 (8) | −0.053 (11) | 0.030 (10) |
C1B | 0.080 (2) | 0.072 (2) | 0.0438 (15) | −0.007 (2) | −0.0165 (14) | −0.0056 (16) |
C2B | 0.085 (2) | 0.089 (3) | 0.0392 (15) | 0.005 (2) | 0.0020 (15) | −0.0032 (17) |
C3B | 0.0657 (19) | 0.089 (3) | 0.0436 (15) | −0.006 (2) | 0.0034 (13) | 0.0104 (18) |
C4B | 0.081 (2) | 0.064 (2) | 0.0444 (15) | −0.0014 (19) | 0.0014 (14) | 0.0084 (16) |
C5B | 0.0577 (17) | 0.069 (2) | 0.0436 (15) | 0.0041 (17) | −0.0015 (12) | 0.0071 (15) |
C6B | 0.074 (2) | 0.072 (2) | 0.0490 (16) | 0.0137 (19) | 0.0038 (14) | 0.0045 (16) |
C7B | 0.080 (2) | 0.0560 (19) | 0.0393 (14) | 0.0049 (18) | 0.0019 (13) | −0.0022 (15) |
C8B | 0.0558 (16) | 0.0504 (17) | 0.0363 (13) | −0.0063 (14) | 0.0009 (11) | 0.0009 (12) |
C9B | 0.0534 (15) | 0.0497 (16) | 0.0337 (12) | −0.0129 (13) | −0.0027 (10) | 0.0007 (12) |
C10B | 0.0567 (17) | 0.066 (2) | 0.0408 (14) | −0.0133 (16) | −0.0063 (12) | 0.0011 (14) |
C12B | 0.0572 (15) | 0.0477 (16) | 0.0379 (12) | −0.0091 (14) | 0.0010 (11) | −0.0062 (12) |
C13B | 0.0542 (15) | 0.0468 (16) | 0.0347 (12) | −0.0061 (13) | −0.0012 (10) | −0.0035 (12) |
C14B | 0.0589 (16) | 0.0452 (16) | 0.0367 (13) | −0.0081 (14) | −0.0053 (11) | −0.0050 (12) |
C16B | 0.078 (2) | 0.057 (2) | 0.0468 (15) | −0.0037 (18) | −0.0125 (14) | −0.0087 (15) |
C17B | 0.0592 (16) | 0.0516 (18) | 0.0399 (13) | −0.0060 (14) | −0.0018 (12) | −0.0040 (13) |
C19B | 0.0590 (19) | 0.096 (3) | 0.075 (2) | −0.024 (2) | −0.0073 (16) | 0.013 (2) |
C20B | 0.0559 (16) | 0.0613 (19) | 0.0454 (15) | 0.0032 (16) | −0.0024 (12) | 0.0003 (14) |
C21B | 0.083 (2) | 0.070 (2) | 0.071 (2) | 0.013 (2) | −0.0159 (18) | −0.014 (2) |
C22B | 0.0645 (18) | 0.067 (2) | 0.0510 (16) | 0.0007 (17) | −0.0082 (14) | −0.0007 (16) |
C23B | 0.0621 (19) | 0.079 (3) | 0.0616 (18) | 0.0030 (19) | −0.0124 (15) | 0.0070 (19) |
C24B | 0.0545 (18) | 0.062 (2) | 0.0546 (18) | 0.0093 (18) | −0.0004 (14) | 0.0035 (18) |
Geometric parameters (Å, º) top
O25A—C3A | 1.218 (4) | O27B—O28D | 1.36 (3) |
O29A—C7A | 1.209 (5) | O27B—O27D | 1.70 (3) |
O26A—C12A | 1.421 (4) | O28B—O28C | 0.54 (5) |
O26A—H26A | 0.80 (4) | O28B—O27D | 1.14 (2) |
O27A—C24A | 1.187 (5) | O28B—C24B | 1.249 (13) |
O28A—C24A | 1.327 (6) | O27C—C24B | 1.17 (2) |
O28A—H28A | 1.11 (5) | O27C—O27D | 1.31 (4) |
C1A—C2A | 1.529 (5) | O27C—O28D | 1.69 (3) |
C1A—C10A | 1.541 (5) | O28C—C24B | 1.19 (2) |
C1A—H11 | 0.9700 | O28C—O28D | 1.47 (4) |
C1A—H12 | 0.9700 | O28C—O27D | 1.52 (3) |
C2A—C3A | 1.495 (5) | O27D—C24B | 1.203 (15) |
C2A—H21 | 0.9700 | O28D—C24B | 1.309 (16) |
C2A—H22 | 0.9700 | C1B—C2B | 1.527 (6) |
C3A—C4A | 1.499 (6) | C1B—C10B | 1.546 (4) |
C4A—C5A | 1.548 (5) | C1B—H13 | 0.9700 |
C4A—H41 | 0.9700 | C1B—H14 | 0.9700 |
C4A—H42 | 0.9700 | C2B—C3B | 1.496 (7) |
C5A—C6A | 1.529 (6) | C2B—H23 | 0.9700 |
C5A—C10A | 1.548 (5) | C2B—H24 | 0.9700 |
C5A—H5A | 0.9800 | C3B—C4B | 1.500 (5) |
C6A—C7A | 1.513 (6) | C4B—C5B | 1.536 (5) |
C6A—H61 | 0.9700 | C4B—H43 | 0.9700 |
C6A—H62 | 0.9700 | C4B—H44 | 0.9700 |
C7A—C8A | 1.522 (5) | C5B—C6B | 1.538 (5) |
C8A—C14A | 1.519 (5) | C5B—C10B | 1.546 (5) |
C8A—C9A | 1.559 (4) | C5B—H5B | 0.9800 |
C8A—H8A | 0.9800 | C6B—C7B | 1.509 (5) |
C9A—C11A | 1.523 (5) | C6B—H63 | 0.9700 |
C9A—C10A | 1.559 (4) | C6B—H64 | 0.9700 |
C9A—H9A | 0.9800 | C7B—C8B | 1.506 (5) |
C10A—C19A | 1.540 (5) | C8B—C14B | 1.535 (4) |
C11A—C12A | 1.536 (4) | C8B—C9B | 1.558 (4) |
C11A—H111 | 0.9700 | C8B—H8B | 0.9800 |
C11A—H112 | 0.9700 | C9B—C11B | 1.542 (5) |
C12A—C13A | 1.540 (4) | C9B—C10B | 1.551 (4) |
C12A—H12A | 0.9800 | C9B—H9B | 0.9800 |
C13A—C18A | 1.541 (4) | C10B—C19B | 1.542 (5) |
C13A—C14A | 1.549 (5) | C11B—C12B | 1.522 (4) |
C13A—C17A | 1.562 (4) | C11B—H113 | 0.9700 |
C14A—C15A | 1.528 (5) | C11B—H114 | 0.9700 |
C14A—H14A | 0.9800 | C12B—C13B | 1.542 (4) |
C15A—C16A | 1.538 (6) | C12B—H12B | 0.9800 |
C15A—H151 | 0.9700 | C13B—C18B | 1.536 (4) |
C15A—H152 | 0.9700 | C13B—C14B | 1.540 (4) |
C16A—C17A | 1.551 (5) | C13B—C17B | 1.560 (4) |
C16A—H161 | 0.9700 | C14B—C15B | 1.525 (4) |
C16A—H162 | 0.9700 | C14B—H14B | 0.9800 |
C17A—C20A | 1.541 (5) | C15B—C16B | 1.548 (5) |
C17A—H17A | 0.9800 | C15B—H153 | 0.9700 |
C18A—H181 | 0.9600 | C15B—H154 | 0.9700 |
C18A—H182 | 0.9600 | C16B—C17B | 1.560 (5) |
C18A—H183 | 0.9600 | C16B—H163 | 0.9700 |
C19A—H191 | 0.9600 | C16B—H164 | 0.9700 |
C19A—H192 | 0.9600 | C17B—C20B | 1.535 (5) |
C19A—H193 | 0.9600 | C17B—H17B | 0.9800 |
C20A—C21A | 1.513 (6) | C18B—H184 | 0.9600 |
C20A—C22A | 1.539 (5) | C18B—H185 | 0.9600 |
C20A—H20A | 0.9800 | C18B—H186 | 0.9600 |
C21A—H211 | 0.9600 | C19B—H194 | 0.9600 |
C21A—H212 | 0.9600 | C19B—H195 | 0.9600 |
C21A—H213 | 0.9600 | C19B—H196 | 0.9600 |
C22A—C23A | 1.530 (6) | C20B—C21B | 1.528 (5) |
C22A—H221 | 0.9700 | C20B—C22B | 1.548 (4) |
C22A—H222 | 0.9700 | C20B—H20B | 0.9800 |
C23A—C24A | 1.489 (6) | C21B—H214 | 0.9600 |
C23A—H231 | 0.9700 | C21B—H215 | 0.9600 |
C23A—H232 | 0.9700 | C21B—H216 | 0.9600 |
O25B—C3B | 1.215 (5) | C22B—C23B | 1.520 (5) |
O29B—C7B | 1.212 (5) | C22B—H223 | 0.9700 |
O26B—C12B | 1.439 (4) | C22B—H224 | 0.9700 |
O26B—H26B | 0.83 (5) | C23B—C24B | 1.493 (4) |
O27B—O27C | 0.50 (5) | C23B—H233 | 0.9700 |
O27B—C24B | 1.239 (11) | C23B—H234 | 0.9700 |
| | | |
C12A—O26A—H26A | 114 (3) | O27C—O27D—O28C | 93 (2) |
C24A—O28A—H28A | 113 (3) | O28B—O27D—O27B | 97.3 (13) |
C2A—C1A—C10A | 114.1 (3) | C24B—O27D—O27B | 46.8 (10) |
C2A—C1A—H11 | 108.7 | O27C—O27D—O27B | 12.0 (15) |
C10A—C1A—H11 | 108.7 | O28C—O27D—O27B | 80.7 (18) |
C2A—C1A—H12 | 108.7 | C24B—O28D—O27B | 55.3 (10) |
C10A—C1A—H12 | 108.7 | C24B—O28D—O28C | 50.6 (12) |
H11—C1A—H12 | 107.6 | O27B—O28D—O28C | 95.1 (16) |
C3A—C2A—C1A | 109.6 (3) | C24B—O28D—O27C | 43.6 (11) |
C3A—C2A—H21 | 109.7 | O27B—O28D—O27C | 14.5 (16) |
C1A—C2A—H21 | 109.7 | O28C—O28D—O27C | 80.7 (17) |
C3A—C2A—H22 | 109.7 | C2B—C1B—C10B | 114.7 (3) |
C1A—C2A—H22 | 109.7 | C2B—C1B—H13 | 108.6 |
H21—C2A—H22 | 108.2 | C10B—C1B—H13 | 108.6 |
O25A—C3A—C2A | 122.5 (4) | C2B—C1B—H14 | 108.6 |
O25A—C3A—C4A | 121.3 (4) | C10B—C1B—H14 | 108.6 |
C2A—C3A—C4A | 116.2 (3) | H13—C1B—H14 | 107.6 |
C3A—C4A—C5A | 113.3 (3) | C3B—C2B—C1B | 109.9 (3) |
C3A—C4A—H41 | 108.9 | C3B—C2B—H23 | 109.7 |
C5A—C4A—H41 | 108.9 | C1B—C2B—H23 | 109.7 |
C3A—C4A—H42 | 108.9 | C3B—C2B—H24 | 109.7 |
C5A—C4A—H42 | 108.9 | C1B—C2B—H24 | 109.7 |
H41—C4A—H42 | 107.7 | H23—C2B—H24 | 108.2 |
C6A—C5A—C4A | 108.6 (3) | O25B—C3B—C2B | 123.3 (4) |
C6A—C5A—C10A | 113.2 (3) | O25B—C3B—C4B | 121.8 (4) |
C4A—C5A—C10A | 112.7 (3) | C2B—C3B—C4B | 114.9 (3) |
C6A—C5A—H5A | 107.4 | C3B—C4B—C5B | 112.3 (3) |
C4A—C5A—H5A | 107.4 | C3B—C4B—H43 | 109.2 |
C10A—C5A—H5A | 107.4 | C5B—C4B—H43 | 109.2 |
C7A—C6A—C5A | 112.1 (3) | C3B—C4B—H44 | 109.2 |
C7A—C6A—H61 | 109.2 | C5B—C4B—H44 | 109.2 |
C5A—C6A—H61 | 109.2 | H43—C4B—H44 | 107.9 |
C7A—C6A—H62 | 109.2 | C4B—C5B—C6B | 109.5 (3) |
C5A—C6A—H62 | 109.2 | C4B—C5B—C10B | 113.2 (3) |
H61—C6A—H62 | 107.9 | C6B—C5B—C10B | 111.8 (3) |
O29A—C7A—C6A | 120.9 (4) | C4B—C5B—H5B | 107.3 |
O29A—C7A—C8A | 123.7 (3) | C6B—C5B—H5B | 107.3 |
C6A—C7A—C8A | 115.3 (3) | C10B—C5B—H5B | 107.3 |
C14A—C8A—C7A | 113.6 (3) | C7B—C6B—C5B | 108.8 (3) |
C14A—C8A—C9A | 109.7 (3) | C7B—C6B—H63 | 109.9 |
C7A—C8A—C9A | 110.2 (3) | C5B—C6B—H63 | 109.9 |
C14A—C8A—H8A | 107.7 | C7B—C6B—H64 | 109.9 |
C7A—C8A—H8A | 107.7 | C5B—C6B—H64 | 109.9 |
C9A—C8A—H8A | 107.7 | H63—C6B—H64 | 108.3 |
C11A—C9A—C10A | 113.6 (3) | O29B—C7B—C8B | 123.5 (3) |
C11A—C9A—C8A | 111.5 (2) | O29B—C7B—C6B | 121.9 (4) |
C10A—C9A—C8A | 112.2 (3) | C8B—C7B—C6B | 114.5 (3) |
C11A—C9A—H9A | 106.3 | C7B—C8B—C14B | 114.0 (3) |
C10A—C9A—H9A | 106.3 | C7B—C8B—C9B | 108.4 (2) |
C8A—C9A—H9A | 106.3 | C14B—C8B—C9B | 109.2 (2) |
C19A—C10A—C1A | 106.7 (3) | C7B—C8B—H8B | 108.4 |
C19A—C10A—C5A | 109.6 (3) | C14B—C8B—H8B | 108.4 |
C1A—C10A—C5A | 108.0 (3) | C9B—C8B—H8B | 108.4 |
C19A—C10A—C9A | 111.9 (3) | C11B—C9B—C10B | 113.3 (3) |
C1A—C10A—C9A | 111.5 (3) | C11B—C9B—C8B | 110.1 (2) |
C5A—C10A—C9A | 109.0 (3) | C10B—C9B—C8B | 113.2 (3) |
C9A—C11A—C12A | 113.7 (3) | C11B—C9B—H9B | 106.6 |
C9A—C11A—H111 | 108.8 | C10B—C9B—H9B | 106.6 |
C12A—C11A—H111 | 108.8 | C8B—C9B—H9B | 106.6 |
C9A—C11A—H112 | 108.8 | C19B—C10B—C1B | 106.6 (3) |
C12A—C11A—H112 | 108.8 | C19B—C10B—C5B | 109.4 (3) |
H111—C11A—H112 | 107.7 | C1B—C10B—C5B | 107.6 (3) |
O26A—C12A—C11A | 110.5 (2) | C19B—C10B—C9B | 111.1 (3) |
O26A—C12A—C13A | 109.2 (2) | C1B—C10B—C9B | 112.1 (3) |
C11A—C12A—C13A | 110.3 (3) | C5B—C10B—C9B | 109.9 (3) |
O26A—C12A—H12A | 108.9 | C12B—C11B—C9B | 114.5 (2) |
C11A—C12A—H12A | 108.9 | C12B—C11B—H113 | 108.6 |
C13A—C12A—H12A | 108.9 | C9B—C11B—H113 | 108.6 |
C12A—C13A—C18A | 108.9 (3) | C12B—C11B—H114 | 108.6 |
C12A—C13A—C14A | 108.5 (2) | C9B—C11B—H114 | 108.6 |
C18A—C13A—C14A | 112.2 (3) | H113—C11B—H114 | 107.6 |
C12A—C13A—C17A | 117.5 (3) | O26B—C12B—C11B | 110.5 (2) |
C18A—C13A—C17A | 109.6 (2) | O26B—C12B—C13B | 109.2 (2) |
C14A—C13A—C17A | 100.0 (3) | C11B—C12B—C13B | 111.1 (2) |
C8A—C14A—C15A | 118.6 (3) | O26B—C12B—H12B | 108.7 |
C8A—C14A—C13A | 114.2 (3) | C11B—C12B—H12B | 108.7 |
C15A—C14A—C13A | 103.1 (3) | C13B—C12B—H12B | 108.7 |
C8A—C14A—H14A | 106.7 | C18B—C13B—C14B | 111.6 (3) |
C15A—C14A—H14A | 106.7 | C18B—C13B—C12B | 108.0 (2) |
C13A—C14A—H14A | 106.7 | C14B—C13B—C12B | 109.3 (2) |
C14A—C15A—C16A | 103.8 (3) | C18B—C13B—C17B | 109.5 (2) |
C14A—C15A—H151 | 111.0 | C14B—C13B—C17B | 101.0 (2) |
C16A—C15A—H151 | 111.0 | C12B—C13B—C17B | 117.3 (2) |
C14A—C15A—H152 | 111.0 | C15B—C14B—C8B | 118.6 (3) |
C16A—C15A—H152 | 111.0 | C15B—C14B—C13B | 103.2 (2) |
H151—C15A—H152 | 109.0 | C8B—C14B—C13B | 112.7 (2) |
C15A—C16A—C17A | 107.5 (3) | C15B—C14B—H14B | 107.2 |
C15A—C16A—H161 | 110.2 | C8B—C14B—H14B | 107.2 |
C17A—C16A—H161 | 110.2 | C13B—C14B—H14B | 107.2 |
C15A—C16A—H162 | 110.2 | C14B—C15B—C16B | 103.7 (3) |
C17A—C16A—H162 | 110.2 | C14B—C15B—H153 | 111.0 |
H161—C16A—H162 | 108.5 | C16B—C15B—H153 | 111.0 |
C20A—C17A—C16A | 113.4 (3) | C14B—C15B—H154 | 111.0 |
C20A—C17A—C13A | 118.4 (3) | C16B—C15B—H154 | 111.0 |
C16A—C17A—C13A | 102.5 (3) | H153—C15B—H154 | 109.0 |
C20A—C17A—H17A | 107.3 | C15B—C16B—C17B | 107.3 (2) |
C16A—C17A—H17A | 107.3 | C15B—C16B—H163 | 110.3 |
C13A—C17A—H17A | 107.3 | C17B—C16B—H163 | 110.3 |
C13A—C18A—H181 | 109.5 | C15B—C16B—H164 | 110.3 |
C13A—C18A—H182 | 109.5 | C17B—C16B—H164 | 110.3 |
H181—C18A—H182 | 109.5 | H163—C16B—H164 | 108.5 |
C13A—C18A—H183 | 109.5 | C20B—C17B—C13B | 118.3 (3) |
H181—C18A—H183 | 109.5 | C20B—C17B—C16B | 113.2 (2) |
H182—C18A—H183 | 109.5 | C13B—C17B—C16B | 102.6 (2) |
C10A—C19A—H191 | 109.5 | C20B—C17B—H17B | 107.4 |
C10A—C19A—H192 | 109.5 | C13B—C17B—H17B | 107.4 |
H191—C19A—H192 | 109.5 | C16B—C17B—H17B | 107.4 |
C10A—C19A—H193 | 109.5 | C13B—C18B—H184 | 109.5 |
H191—C19A—H193 | 109.5 | C13B—C18B—H185 | 109.5 |
H192—C19A—H193 | 109.5 | H184—C18B—H185 | 109.5 |
C21A—C20A—C22A | 109.4 (4) | C13B—C18B—H186 | 109.5 |
C21A—C20A—C17A | 112.4 (3) | H184—C18B—H186 | 109.5 |
C22A—C20A—C17A | 110.8 (3) | H185—C18B—H186 | 109.5 |
C21A—C20A—H20A | 108.0 | C10B—C19B—H194 | 109.5 |
C22A—C20A—H20A | 108.0 | C10B—C19B—H195 | 109.5 |
C17A—C20A—H20A | 108.0 | H194—C19B—H195 | 109.5 |
C20A—C21A—H211 | 109.5 | C10B—C19B—H196 | 109.5 |
C20A—C21A—H212 | 109.5 | H194—C19B—H196 | 109.5 |
H211—C21A—H212 | 109.5 | H195—C19B—H196 | 109.5 |
C20A—C21A—H213 | 109.5 | C21B—C20B—C17B | 113.3 (3) |
H211—C21A—H213 | 109.5 | C21B—C20B—C22B | 110.8 (3) |
H212—C21A—H213 | 109.5 | C17B—C20B—C22B | 111.4 (3) |
C23A—C22A—C20A | 113.3 (4) | C21B—C20B—H20B | 107.0 |
C23A—C22A—H221 | 108.9 | C17B—C20B—H20B | 107.0 |
C20A—C22A—H221 | 108.9 | C22B—C20B—H20B | 107.0 |
C23A—C22A—H222 | 108.9 | C20B—C21B—H214 | 109.5 |
C20A—C22A—H222 | 108.9 | C20B—C21B—H215 | 109.5 |
H221—C22A—H222 | 107.7 | H214—C21B—H215 | 109.5 |
C24A—C23A—C22A | 117.2 (4) | C20B—C21B—H216 | 109.5 |
C24A—C23A—H231 | 108.0 | H214—C21B—H216 | 109.5 |
C22A—C23A—H231 | 108.0 | H215—C21B—H216 | 109.5 |
C24A—C23A—H232 | 108.0 | C23B—C22B—C20B | 111.1 (3) |
C22A—C23A—H232 | 108.0 | C23B—C22B—H223 | 109.4 |
H231—C23A—H232 | 107.2 | C20B—C22B—H223 | 109.4 |
O27A—C24A—O28A | 120.9 (4) | C23B—C22B—H224 | 109.4 |
O27A—C24A—C23A | 125.0 (5) | C20B—C22B—H224 | 109.4 |
O28A—C24A—C23A | 114.1 (3) | H223—C22B—H224 | 108.0 |
C12B—O26B—H26B | 111 (3) | C24B—C23B—C22B | 116.1 (3) |
O27C—O27B—C24B | 70 (3) | C24B—C23B—H233 | 108.3 |
O27C—O27B—O28D | 123 (4) | C22B—C23B—H233 | 108.3 |
C24B—O27B—O28D | 60.3 (9) | C24B—C23B—H234 | 108.3 |
O27C—O27B—O27D | 33 (3) | C22B—C23B—H234 | 108.3 |
C24B—O27B—O27D | 45.0 (7) | H233—C23B—H234 | 107.4 |
O28D—O27B—O27D | 90.2 (10) | O27C—C24B—O28C | 120.2 (17) |
O28C—O28B—O27D | 126 (4) | O27C—C24B—O27D | 67 (2) |
O28C—O28B—C24B | 72 (4) | O28C—C24B—O27D | 78.6 (19) |
O27D—O28B—C24B | 60.4 (12) | O27C—C24B—O27B | 24 (2) |
O27B—O27C—C24B | 86 (4) | O28C—C24B—O27B | 118.1 (14) |
O27B—O27C—O27D | 135 (4) | O27D—C24B—O27B | 88.2 (14) |
C24B—O27C—O27D | 57.9 (14) | O27C—C24B—O28B | 111.4 (19) |
O27B—O27C—O28D | 43 (3) | O28C—C24B—O28B | 25 (2) |
C24B—O27C—O28D | 50.7 (12) | O27D—C24B—O28B | 55.2 (13) |
O27D—O27C—O28D | 92.7 (14) | O27B—C24B—O28B | 120.7 (8) |
O28B—O28C—C24B | 83 (4) | O27C—C24B—O28D | 85.7 (19) |
O28B—O28C—O28D | 131 (4) | O28C—C24B—O28D | 71.5 (19) |
C24B—O28C—O28D | 57.9 (14) | O27D—C24B—O28D | 120.4 (8) |
O28B—O28C—O27D | 37 (3) | O27B—C24B—O28D | 64.5 (13) |
C24B—O28C—O27D | 51.0 (12) | O28B—C24B—O28D | 93.6 (13) |
O28D—O28C—O27D | 93.9 (17) | O27C—C24B—C23B | 124.2 (12) |
O28B—O27D—C24B | 64.4 (10) | O28C—C24B—C23B | 115.5 (12) |
O28B—O27D—O27C | 109.3 (18) | O27D—C24B—C23B | 125.8 (7) |
C24B—O27D—O27C | 55.2 (14) | O27B—C24B—C23B | 120.8 (5) |
O28B—O27D—O28C | 16.7 (15) | O28B—C24B—C23B | 118.4 (7) |
C24B—O27D—O28C | 50.5 (13) | O28D—C24B—C23B | 113.6 (7) |
Crystal data top
C24H34O5 | F(000) = 436 |
Mr = 402.51 | Dx = 1.258 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71070 Å |
a = 12.0863 (3) Å | Cell parameters from 3134 reflections |
b = 6.8301 (2) Å | θ = 3.2–30.0° |
c = 13.1153 (4) Å | µ = 0.09 mm−1 |
β = 101.138 (1)° | T = 295 K |
V = 1062.28 (5) Å3 | Prism, colourless |
Z = 2 | 0.40 × 0.26 × 0.12 mm |
Data collection top
Nonius Kappa CCD diffractometer | 2638 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.030 |
Graphite monochromator | θmax = 30.0°, θmin = 3.2° |
ϕ scans and ω scans | h = −17→17 |
16592 measured reflections | k = −9→8 |
3336 independent reflections | l = −18→18 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.038 | All H-atom parameters refined |
wR(F2) = 0.101 | w = 1/[σ2(Fo2) + (0.0503P)2 + 0.0934P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.008 |
3336 reflections | Δρmax = 0.20 e Å−3 |
397 parameters | Δρmin = −0.15 e Å−3 |
0 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.3 (12) |
Crystal data top
C24H34O5 | V = 1062.28 (5) Å3 |
Mr = 402.51 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 12.0863 (3) Å | µ = 0.09 mm−1 |
b = 6.8301 (2) Å | T = 295 K |
c = 13.1153 (4) Å | 0.40 × 0.26 × 0.12 mm |
β = 101.138 (1)° | |
Data collection top
Nonius Kappa CCD diffractometer | 2638 reflections with I > 2σ(I) |
16592 measured reflections | Rint = 0.030 |
3336 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.038 | All H-atom parameters refined |
wR(F2) = 0.101 | Δρmax = 0.20 e Å−3 |
S = 1.05 | Δρmin = −0.15 e Å−3 |
3336 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
397 parameters | Absolute structure parameter: −0.3 (12) |
0 restraints | |
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 | x | y | z | Uiso*/Ueq | |
C1 | 0.7791 (2) | 0.2135 | −0.21461 (16) | 0.0480 (5) | |
C2 | 0.6780 (3) | 0.0819 (5) | −0.25541 (19) | 0.0615 (6) | |
C3 | 0.5747 (2) | 0.2011 (6) | −0.29198 (17) | 0.0592 (6) | |
C4 | 0.55089 (18) | 0.3568 (5) | −0.21917 (17) | 0.0512 (5) | |
C5 | 0.65509 (15) | 0.4809 (5) | −0.17219 (14) | 0.0369 (4) | |
C6 | 0.62475 (18) | 0.6189 (5) | −0.08946 (15) | 0.0421 (4) | |
C7 | 0.61213 (15) | 0.5102 (5) | 0.00811 (14) | 0.0350 (4) | |
C8 | 0.71572 (14) | 0.3918 (4) | 0.05512 (12) | 0.0291 (3) | |
C9 | 0.74277 (14) | 0.2477 (4) | −0.02885 (12) | 0.0282 (3) | |
C10 | 0.76095 (14) | 0.3563 (5) | −0.12841 (13) | 0.0323 (3) | |
C11 | 0.84169 (17) | 0.1103 (5) | 0.01662 (14) | 0.0372 (4) | |
C12 | 0.82841 (15) | 0.0220 (5) | 0.11927 (13) | 0.0324 (3) | |
C13 | 0.81672 (14) | 0.1707 (4) | 0.20229 (12) | 0.0296 (3) | |
C14 | 0.70515 (14) | 0.2804 (4) | 0.15335 (12) | 0.0300 (3) | |
C15 | 0.6758 (2) | 0.3922 (5) | 0.24512 (16) | 0.0441 (5) | |
C16 | 0.7183 (2) | 0.2608 (5) | 0.34017 (16) | 0.0492 (5) | |
C17 | 0.78585 (16) | 0.0899 (5) | 0.30341 (13) | 0.0344 (4) | |
C18 | 0.91875 (17) | 0.3092 (5) | 0.22586 (16) | 0.0403 (4) | |
C19 | 0.86450 (17) | 0.4908 (5) | −0.10589 (18) | 0.0466 (5) | |
C20 | 0.88291 (17) | 0.0198 (5) | 0.39006 (14) | 0.0408 (4) | |
C21 | 0.9561 (2) | −0.1404 (6) | 0.3549 (2) | 0.0571 (6) | |
C22 | 0.8394 (2) | −0.0476 (5) | 0.48764 (16) | 0.0488 (5) | |
C23 | 0.7519 (3) | −0.2074 (6) | 0.46712 (18) | 0.0695 (9) | |
C24 | 0.7356 (2) | −0.3162 (5) | 0.56145 (15) | 0.0490 (5) | |
O25 | 0.51246 (19) | 0.1696 (6) | −0.37494 (14) | 0.0955 (8) | |
O26 | 0.81794 (15) | −0.1530 (4) | 0.12880 (12) | 0.0530 (4) | |
O27 | 0.80454 (15) | −0.3320 (5) | 0.63925 (13) | 0.0749 (6) | |
O28 | 0.63630 (17) | −0.4032 (6) | 0.55638 (14) | 0.0843 (7) | |
O29 | 0.52567 (12) | 0.5113 (4) | 0.04174 (12) | 0.0543 (4) | |
H1A | 0.847 (2) | 0.133 (5) | −0.190 (2) | 0.058 (7)* | |
H1B | 0.791 (2) | 0.292 (4) | −0.2795 (19) | 0.051 (7)* | |
H2A | 0.669 (3) | −0.008 (6) | −0.198 (3) | 0.097 (11)* | |
H2B | 0.701 (2) | −0.020 (5) | −0.311 (2) | 0.077 (9)* | |
H4A | 0.486 (3) | 0.443 (5) | −0.255 (2) | 0.078 (9)* | |
H4B | 0.517 (2) | 0.287 (4) | −0.160 (2) | 0.059 (7)* | |
H5 | 0.674 (2) | 0.565 (4) | −0.228 (2) | 0.052 (7)* | |
H6A | 0.687 (2) | 0.714 (4) | −0.0687 (18) | 0.051 (7)* | |
H6B | 0.555 (2) | 0.686 (4) | −0.1161 (18) | 0.051 (7)* | |
H8 | 0.7743 (18) | 0.487 (4) | 0.0726 (17) | 0.041 (6)* | |
H9 | 0.6744 (16) | 0.162 (3) | −0.0447 (14) | 0.027 (5)* | |
H11A | 0.844 (2) | −0.002 (5) | −0.031 (2) | 0.067 (8)* | |
H11B | 0.915 (2) | 0.185 (4) | 0.0287 (18) | 0.055 (7)* | |
H14 | 0.6462 (17) | 0.180 (4) | 0.1316 (16) | 0.038 (5)* | |
H15A | 0.712 (2) | 0.517 (5) | 0.251 (2) | 0.061 (8)* | |
H15B | 0.600 (3) | 0.422 (5) | 0.235 (2) | 0.069 (8)* | |
H16A | 0.766 (3) | 0.336 (5) | 0.395 (2) | 0.072 (9)* | |
H16B | 0.654 (3) | 0.211 (5) | 0.375 (2) | 0.074 (9)* | |
H17 | 0.7377 (18) | −0.017 (4) | 0.2845 (17) | 0.037 (5)* | |
H18A | 0.989 (2) | 0.238 (5) | 0.2595 (19) | 0.055 (7)* | |
H18B | 0.907 (2) | 0.405 (4) | 0.274 (2) | 0.058 (7)* | |
H18C | 0.932 (2) | 0.374 (5) | 0.168 (2) | 0.059 (7)* | |
H19A | 0.868 (2) | 0.562 (5) | −0.166 (2) | 0.066 (8)* | |
H19B | 0.866 (2) | 0.593 (5) | −0.043 (2) | 0.063 (7)* | |
H19C | 0.936 (2) | 0.412 (5) | −0.089 (2) | 0.063 (8)* | |
H20 | 0.932 (2) | 0.131 (4) | 0.4136 (18) | 0.049 (6)* | |
H21A | 0.903 (3) | −0.250 (7) | 0.335 (3) | 0.102 (12)* | |
H21B | 0.993 (3) | −0.086 (5) | 0.297 (3) | 0.079 (9)* | |
H21C | 1.015 (3) | −0.173 (7) | 0.411 (3) | 0.097 (11)* | |
H22A | 0.906 (2) | −0.096 (4) | 0.542 (2) | 0.059 (7)* | |
H22B | 0.809 (2) | 0.055 (5) | 0.515 (2) | 0.058 (8)* | |
H23A | 0.776 (5) | −0.310 (10) | 0.417 (4) | 0.16 (2)* | |
H23B | 0.688 (3) | −0.185 (8) | 0.425 (3) | 0.109 (14)* | |
H28 | 0.597 (3) | −0.388 (7) | 0.495 (3) | 0.098 (11)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0540 (12) | 0.0582 (13) | 0.0341 (9) | 0.0068 (11) | 0.0137 (9) | 0.0010 (9) |
C2 | 0.0892 (19) | 0.0546 (13) | 0.0405 (11) | −0.0082 (13) | 0.0116 (12) | −0.0090 (11) |
C3 | 0.0635 (14) | 0.0680 (16) | 0.0411 (11) | −0.0251 (13) | −0.0026 (10) | 0.0044 (11) |
C4 | 0.0343 (10) | 0.0683 (15) | 0.0462 (11) | −0.0047 (10) | −0.0044 (8) | 0.0129 (11) |
C5 | 0.0337 (9) | 0.0437 (10) | 0.0328 (9) | 0.0003 (8) | 0.0048 (7) | 0.0119 (8) |
C6 | 0.0421 (10) | 0.0391 (10) | 0.0446 (10) | 0.0099 (9) | 0.0075 (8) | 0.0146 (9) |
C7 | 0.0375 (9) | 0.0314 (8) | 0.0368 (8) | 0.0080 (7) | 0.0087 (7) | 0.0055 (7) |
C8 | 0.0306 (8) | 0.0266 (7) | 0.0297 (8) | 0.0023 (6) | 0.0048 (6) | 0.0023 (6) |
C9 | 0.0271 (8) | 0.0307 (7) | 0.0264 (7) | 0.0015 (6) | 0.0045 (6) | 0.0027 (6) |
C10 | 0.0277 (8) | 0.0386 (9) | 0.0304 (8) | −0.0015 (7) | 0.0055 (6) | 0.0060 (7) |
C11 | 0.0413 (10) | 0.0396 (9) | 0.0314 (8) | 0.0126 (8) | 0.0089 (7) | 0.0046 (8) |
C12 | 0.0340 (9) | 0.0309 (8) | 0.0307 (8) | 0.0054 (7) | 0.0019 (6) | 0.0005 (7) |
C13 | 0.0320 (8) | 0.0286 (7) | 0.0265 (7) | 0.0018 (6) | 0.0012 (6) | 0.0020 (6) |
C14 | 0.0318 (8) | 0.0301 (8) | 0.0286 (7) | 0.0035 (7) | 0.0069 (6) | 0.0025 (6) |
C15 | 0.0567 (13) | 0.0421 (11) | 0.0355 (9) | 0.0162 (10) | 0.0139 (9) | 0.0008 (8) |
C16 | 0.0667 (14) | 0.0503 (12) | 0.0325 (9) | 0.0144 (11) | 0.0141 (9) | 0.0025 (9) |
C17 | 0.0415 (9) | 0.0334 (8) | 0.0272 (7) | −0.0015 (8) | 0.0036 (7) | 0.0022 (7) |
C18 | 0.0400 (10) | 0.0383 (10) | 0.0396 (10) | −0.0061 (8) | 0.0001 (8) | 0.0036 (8) |
C19 | 0.0345 (10) | 0.0565 (13) | 0.0488 (11) | −0.0097 (9) | 0.0079 (8) | 0.0128 (10) |
C20 | 0.0482 (11) | 0.0392 (9) | 0.0306 (9) | −0.0046 (9) | −0.0033 (8) | 0.0039 (8) |
C21 | 0.0566 (14) | 0.0618 (15) | 0.0498 (13) | 0.0174 (12) | 0.0021 (11) | 0.0143 (11) |
C22 | 0.0681 (14) | 0.0447 (11) | 0.0299 (9) | −0.0083 (10) | −0.0002 (9) | 0.0040 (8) |
C23 | 0.097 (2) | 0.0736 (19) | 0.0331 (11) | −0.0384 (16) | −0.0005 (12) | 0.0123 (11) |
C24 | 0.0598 (13) | 0.0516 (11) | 0.0353 (9) | −0.0016 (10) | 0.0081 (9) | 0.0104 (9) |
O25 | 0.0957 (15) | 0.127 (2) | 0.0502 (10) | −0.0371 (15) | −0.0195 (10) | −0.0068 (12) |
O26 | 0.0842 (11) | 0.0295 (7) | 0.0438 (8) | 0.0029 (7) | 0.0083 (7) | −0.0007 (6) |
O27 | 0.0646 (10) | 0.1038 (16) | 0.0502 (9) | −0.0076 (11) | −0.0041 (8) | 0.0376 (10) |
O28 | 0.0712 (12) | 0.127 (2) | 0.0493 (10) | −0.0294 (13) | −0.0013 (9) | 0.0360 (12) |
O29 | 0.0428 (8) | 0.0616 (9) | 0.0626 (9) | 0.0185 (7) | 0.0205 (7) | 0.0207 (8) |
Geometric parameters (Å, º) top
C1—C2 | 1.528 (4) | C13—C17 | 1.547 (2) |
C1—C10 | 1.541 (3) | C13—C14 | 1.568 (2) |
C1—H1A | 0.99 (3) | C14—C15 | 1.524 (2) |
C1—H1B | 1.04 (2) | C14—H14 | 0.99 (2) |
C2—C3 | 1.490 (4) | C15—C16 | 1.541 (3) |
C2—H2A | 1.00 (4) | C15—H15A | 0.95 (3) |
C2—H2B | 1.09 (3) | C15—H15B | 0.93 (3) |
C3—O25 | 1.216 (3) | C16—C17 | 1.554 (3) |
C3—C4 | 1.494 (4) | C16—H16A | 0.98 (3) |
C4—C5 | 1.544 (3) | C16—H16B | 1.03 (3) |
C4—H4A | 1.02 (3) | C17—C20 | 1.543 (2) |
C4—H4B | 1.06 (3) | C17—H17 | 0.94 (3) |
C5—C6 | 1.534 (3) | C18—H18A | 1.00 (3) |
C5—C10 | 1.551 (2) | C18—H18B | 0.94 (3) |
C5—H5 | 0.99 (3) | C18—H18C | 0.92 (3) |
C6—C7 | 1.512 (2) | C19—H19A | 0.93 (3) |
C6—H6A | 0.99 (3) | C19—H19B | 1.08 (3) |
C6—H6B | 0.96 (3) | C19—H19C | 1.01 (3) |
C7—O29 | 1.210 (2) | C20—C21 | 1.533 (3) |
C7—C8 | 1.518 (2) | C20—C22 | 1.545 (3) |
C8—C14 | 1.523 (2) | C20—H20 | 0.98 (3) |
C8—C9 | 1.558 (2) | C21—H21A | 0.99 (4) |
C8—H8 | 0.96 (2) | C21—H21B | 1.02 (3) |
C9—C11 | 1.546 (2) | C21—H21C | 0.95 (4) |
C9—C10 | 1.554 (2) | C22—C23 | 1.507 (3) |
C9—H9 | 1.00 (2) | C22—H22A | 1.02 (3) |
C10—C19 | 1.535 (3) | C22—H22B | 0.90 (3) |
C11—C12 | 1.512 (2) | C23—C24 | 1.489 (3) |
C11—H11A | 0.99 (3) | C23—H23A | 1.04 (6) |
C11—H11B | 1.01 (3) | C23—H23B | 0.88 (4) |
C12—O26 | 1.211 (2) | C24—O27 | 1.191 (3) |
C12—C13 | 1.516 (2) | C24—O28 | 1.329 (3) |
C13—C18 | 1.537 (2) | O28—H28 | 0.86 (4) |
| | | |
C2—C1—C10 | 114.30 (17) | C18—C13—C14 | 112.43 (14) |
C2—C1—H1A | 110.3 (17) | C17—C13—C14 | 101.00 (13) |
C10—C1—H1A | 109.4 (16) | C8—C14—C15 | 119.23 (14) |
C2—C1—H1B | 104.3 (14) | C8—C14—C13 | 112.28 (13) |
C10—C1—H1B | 109.8 (14) | C15—C14—C13 | 103.23 (14) |
H1A—C1—H1B | 108.5 (19) | C8—C14—H14 | 106.0 (12) |
C3—C2—C1 | 110.8 (2) | C15—C14—H14 | 108.1 (12) |
C3—C2—H2A | 112 (2) | C13—C14—H14 | 107.6 (13) |
C1—C2—H2A | 107 (2) | C14—C15—C16 | 104.79 (15) |
C3—C2—H2B | 116.0 (16) | C14—C15—H15A | 110.1 (17) |
C1—C2—H2B | 108.9 (16) | C16—C15—H15A | 112.2 (17) |
H2A—C2—H2B | 101 (3) | C14—C15—H15B | 111.9 (19) |
O25—C3—C2 | 121.7 (3) | C16—C15—H15B | 114.4 (18) |
O25—C3—C4 | 122.4 (3) | H15A—C15—H15B | 104 (3) |
C2—C3—C4 | 115.83 (19) | C15—C16—C17 | 107.41 (15) |
C3—C4—C5 | 113.77 (18) | C15—C16—H16A | 110 (2) |
C3—C4—H4A | 109.9 (18) | C17—C16—H16A | 110 (2) |
C5—C4—H4A | 111.0 (19) | C15—C16—H16B | 112.7 (18) |
C3—C4—H4B | 107.6 (15) | C17—C16—H16B | 112.1 (19) |
C5—C4—H4B | 110.7 (14) | H16A—C16—H16B | 104 (2) |
H4A—C4—H4B | 103 (2) | C20—C17—C13 | 117.84 (15) |
C6—C5—C4 | 109.37 (16) | C20—C17—C16 | 112.02 (16) |
C6—C5—C10 | 111.59 (15) | C13—C17—C16 | 103.06 (15) |
C4—C5—C10 | 113.42 (17) | C20—C17—H17 | 107.4 (14) |
C6—C5—H5 | 106.5 (15) | C13—C17—H17 | 107.0 (13) |
C4—C5—H5 | 108.2 (15) | C16—C17—H17 | 109.3 (13) |
C10—C5—H5 | 107.5 (14) | C13—C18—H18A | 111.6 (17) |
C7—C6—C5 | 111.94 (16) | C13—C18—H18B | 110.2 (16) |
C7—C6—H6A | 106.5 (14) | H18A—C18—H18B | 105 (2) |
C5—C6—H6A | 108.8 (14) | C13—C18—H18C | 112.7 (18) |
C7—C6—H6B | 108.5 (14) | H18A—C18—H18C | 110 (2) |
C5—C6—H6B | 110.3 (14) | H18B—C18—H18C | 107 (2) |
H6A—C6—H6B | 111 (2) | C10—C19—H19A | 108.1 (18) |
O29—C7—C6 | 122.72 (16) | C10—C19—H19B | 115.1 (14) |
O29—C7—C8 | 123.91 (16) | H19A—C19—H19B | 108 (2) |
C6—C7—C8 | 113.28 (14) | C10—C19—H19C | 111.1 (17) |
C7—C8—C14 | 114.37 (13) | H19A—C19—H19C | 107 (2) |
C7—C8—C9 | 108.59 (13) | H19B—C19—H19C | 107 (2) |
C14—C8—C9 | 110.22 (13) | C21—C20—C17 | 113.62 (17) |
C7—C8—H8 | 104.4 (14) | C21—C20—C22 | 110.19 (19) |
C14—C8—H8 | 108.4 (13) | C17—C20—C22 | 111.74 (17) |
C9—C8—H8 | 110.7 (13) | C21—C20—H20 | 107.3 (14) |
C11—C9—C10 | 112.92 (13) | C17—C20—H20 | 108.7 (15) |
C11—C9—C8 | 111.28 (13) | C22—C20—H20 | 104.8 (13) |
C10—C9—C8 | 112.04 (14) | C20—C21—H21A | 104 (2) |
C11—C9—H9 | 105.8 (12) | C20—C21—H21B | 108.8 (19) |
C10—C9—H9 | 110.5 (11) | H21A—C21—H21B | 116 (3) |
C8—C9—H9 | 103.7 (11) | C20—C21—H21C | 109 (2) |
C19—C10—C1 | 107.09 (16) | H21A—C21—H21C | 112 (3) |
C19—C10—C5 | 109.06 (16) | H21B—C21—H21C | 107 (3) |
C1—C10—C5 | 107.45 (15) | C23—C22—C20 | 114.04 (18) |
C19—C10—C9 | 111.50 (15) | C23—C22—H22A | 108.7 (17) |
C1—C10—C9 | 112.19 (16) | C20—C22—H22A | 108.8 (14) |
C5—C10—C9 | 109.42 (13) | C23—C22—H22B | 107.9 (18) |
C12—C11—C9 | 112.24 (14) | C20—C22—H22B | 109.5 (18) |
C12—C11—H11A | 105.7 (18) | H22A—C22—H22B | 108 (2) |
C9—C11—H11A | 109.9 (17) | C24—C23—C22 | 114.5 (2) |
C12—C11—H11B | 107.7 (14) | C24—C23—H23A | 107 (3) |
C9—C11—H11B | 110.2 (16) | C22—C23—H23A | 109 (3) |
H11A—C11—H11B | 111 (2) | C24—C23—H23B | 111 (3) |
O26—C12—C11 | 121.13 (17) | C22—C23—H23B | 119 (3) |
O26—C12—C13 | 124.15 (17) | H23A—C23—H23B | 93 (4) |
C11—C12—C13 | 114.39 (15) | O27—C24—O28 | 118.6 (2) |
C12—C13—C18 | 111.98 (15) | O27—C24—C23 | 125.0 (2) |
C12—C13—C17 | 116.61 (14) | O28—C24—C23 | 116.4 (2) |
C18—C13—C17 | 111.36 (14) | C24—O28—H28 | 109 (3) |
C12—C13—C14 | 102.61 (12) | | |
Experimental details
| (I) | (II) | (III) | (IV-alpha) |
Crystal data |
Chemical formula | C24H38O5 | C24H38O5 | C24H36O5 | C24H36O5 |
Mr | 406.54 | 406.54 | 404.53 | 404.53 |
Crystal system, space group | Orthorhombic, P212121 | Orthorhombic, P212121 | Monoclinic, P21 | Orthorhombic, P212121 |
Temperature (K) | 295 | 295 | 295 | 295 |
a, b, c (Å) | 8.9879 (1), 9.4028 (1), 26.4369 (4) | 6.3122 (1), 10.8884 (2), 32.0624 (7) | 10.2677 (4), 7.1108 (2), 15.2270 (6) | 8.4953 (1), 12.7060 (2), 20.8011 (3) |
α, β, γ (°) | 90, 90, 90 | 90, 90, 90 | 90, 92.340 (1), 90 | 90, 90, 90 |
V (Å3) | 2234.22 (5) | 2203.64 (7) | 1110.82 (7) | 2245.30 (5) |
Z | 4 | 4 | 2 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.08 | 0.08 | 0.08 | 0.08 |
Crystal size (mm) | 0.42 × 0.35 × 0.28 | 0.36 × 0.14 × 0.10 | 0.25 × 0.11 × 0.06 | 0.45 × 0.35 × 0.32 |
|
Data collection |
Diffractometer | Nonius Kappa CCD diffractometer | Nonius Kappa CCD diffractometer | Nonius Kappa CCD diffractometer | Nonius Kappa CCD diffractometer |
Absorption correction | – | – | – | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 24241, 3049, 2385 | 13705, 3006, 2415 | 14953, 2721, 2236 | 26164, 3664, 3189 |
Rint | 0.041 | 0.076 | 0.039 | 0.035 |
(sin θ/λ)max (Å−1) | 0.661 | 0.661 | 0.650 | 0.703 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.110, 1.04 | 0.044, 0.120, 1.04 | 0.041, 0.107, 1.05 | 0.050, 0.146, 1.06 |
No. of reflections | 3049 | 3006 | 2721 | 3664 |
No. of parameters | 277 | 277 | 273 | 406 |
No. of restraints | 0 | 0 | 1 | 0 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.15, −0.13 | 0.16, −0.16 | 0.15, −0.14 | 0.45, −0.32 |
Absolute structure | Flack H D (1983), Acta Cryst. A39, 876-881 | Flack H D (1983), Acta Cryst. A39, 876-881 | Flack H D (1983), Acta Cryst. A39, 876-881 | Flack H D (1983), Acta Cryst. A39, 876-881 |
Absolute structure parameter | −3.4 (15) | 1.2 (15) | 0.2 (14) | −0.3 (15) |
| (IV-beta) | (V) |
Crystal data |
Chemical formula | C24H36O5·1/2(H2O) | C24H34O5 |
Mr | 413.54 | 402.51 |
Crystal system, space group | Monoclinic, C2 | Monoclinic, P21 |
Temperature (K) | 295 | 295 |
a, b, c (Å) | 26.6049 (4), 7.7044 (1), 22.9126 (3) | 12.0863 (3), 6.8301 (2), 13.1153 (4) |
α, β, γ (°) | 90, 93.424 (1), 90 | 90, 101.138 (1), 90 |
V (Å3) | 4688.1 (1) | 1062.28 (5) |
Z | 8 | 2 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.08 | 0.09 |
Crystal size (mm) | 0.35 × 0.12 × 0.08 | 0.40 × 0.26 × 0.12 |
|
Data collection |
Diffractometer | Nonius Kappa CCD diffractometer | Nonius Kappa CCD diffractometer |
Absorption correction | – | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 26846, 5683, 4381 | 16592, 3336, 2638 |
Rint | 0.034 | 0.030 |
(sin θ/λ)max (Å−1) | 0.650 | 0.704 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.166, 1.01 | 0.038, 0.101, 1.05 |
No. of reflections | 5683 | 3336 |
No. of parameters | 567 | 397 |
No. of restraints | 0 | 0 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.35, −0.27 | 0.20, −0.15 |
Absolute structure | Flack H D (1983), Acta Cryst. A39, 876-881 | Flack H D (1983), Acta Cryst. A39, 876-881 |
Absolute structure parameter | 1.6 (15) | −0.3 (12) |