Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805029387/bt6736sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805029387/bt6736Isup2.hkl |
CCDC reference: 287475
Epivernodalol was isolated from an ethanolic extract and acetylated according to the method of Koul et al. (2003). It was crystallized from ethyl acetate/petroleum ether (1:4) (m.p. 381 K). MS (diacetate of 2): m/z at M+ 476 (5), 474 (19), 435 (5), 357 (3), 329 (5), 316 (8), 291 (54), 273 (24), 244 (33), 214 (25), 182 (26), 154 (27), 136 (9), 127 (100).
H atoms were placed in calculated positions (C—H = 0.93–0.97 Å) with Uiso values constrained to be 1.5Ueq of the carrier atom for the methyl H atoms and 1.2Ueq for the remaining H atoms. The methyl groups were allowed to rotate but not to tip. The absolute configuration was assigned arbitrarily.
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97, PARST95 (Nardelli, 1995) and PLATON (Spek, 2001).
C24H28O10 | F(000) = 1008 |
Mr = 476.46 | Dx = 1.276 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 14723 reflections |
a = 8.0887 (2) Å | θ = 3.0–25.3° |
b = 12.8750 (4) Å | µ = 0.10 mm−1 |
c = 23.8205 (8) Å | T = 291 K |
V = 2480.71 (13) Å3 | Needle, colourless |
Z = 4 | 0.20 × 0.05 × 0.05 mm |
Nonius KappaCCD diffractometer | 1373 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.069 |
Graphite monochromator | θmax = 25.3°, θmin = 3.0° |
Detector resolution: 19 vertical, 18 horizontal pixels mm-1 | h = −9→9 |
208 frames via ω–rotation (Δω=1°) and two times 60 s per frame (two sets at different κ–angles) scans | k = −15→15 |
14723 measured reflections | l = −28→28 |
2589 independent reflections |
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)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.115 | w = 1/[σ2(Fo2) + (0.0643P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.87 | (Δ/σ)max < 0.001 |
2589 reflections | Δρmax = 0.23 e Å−3 |
311 parameters | Δρmin = −0.14 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0057 (15) |
C24H28O10 | V = 2480.71 (13) Å3 |
Mr = 476.46 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 8.0887 (2) Å | µ = 0.10 mm−1 |
b = 12.8750 (4) Å | T = 291 K |
c = 23.8205 (8) Å | 0.20 × 0.05 × 0.05 mm |
Nonius KappaCCD diffractometer | 1373 reflections with I > 2σ(I) |
14723 measured reflections | Rint = 0.069 |
2589 independent reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.115 | H-atom parameters constrained |
S = 0.87 | Δρmax = 0.23 e Å−3 |
2589 reflections | Δρmin = −0.14 e Å−3 |
311 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.3229 (4) | −0.1415 (2) | −0.05742 (10) | 0.0680 (8) | |
O2 | 0.1082 (4) | −0.2420 (3) | −0.06704 (12) | 0.0796 (9) | |
O3 | 0.5712 (3) | 0.1161 (2) | 0.12470 (10) | 0.0635 (8) | |
O4 | 1.0192 (5) | 0.3231 (4) | 0.18172 (17) | 0.1296 (15) | |
O5 | 0.8171 (4) | 0.0850 (3) | 0.08519 (16) | 0.1040 (12) | |
O6 | 1.1947 (12) | 0.3692 (8) | 0.1219 (4) | 0.317 (6) | |
O7 | 0.4565 (4) | −0.0040 (2) | 0.27571 (11) | 0.0845 (10) | |
O8 | 0.2769 (5) | 0.0919 (3) | 0.22997 (13) | 0.1210 (16) | |
O9 | 0.1151 (3) | −0.1157 (2) | 0.12516 (10) | 0.0597 (7) | |
O10 | 0.1825 (5) | −0.2838 (3) | 0.11700 (17) | 0.0995 (12) | |
C1 | 0.1829 (5) | −0.0341 (3) | 0.03763 (15) | 0.0527 (10) | |
H1 | 0.1065 | 0.0207 | 0.0496 | 0.063* | |
C2 | 0.3158 (5) | 0.0179 (3) | 0.00147 (15) | 0.0569 (11) | |
C3 | 0.4274 (5) | 0.0893 (3) | 0.03653 (15) | 0.0625 (11) | |
H3A | 0.5211 | 0.1107 | 0.0139 | 0.075* | |
H3B | 0.3660 | 0.1512 | 0.0467 | 0.075* | |
C4 | 0.4906 (5) | 0.0372 (3) | 0.08978 (15) | 0.0588 (11) | |
H4 | 0.5680 | −0.0188 | 0.0806 | 0.071* | |
C5 | 0.3490 (5) | −0.0036 (3) | 0.12536 (14) | 0.0526 (10) | |
H5 | 0.2745 | 0.0548 | 0.1330 | 0.063* | |
C6 | 0.2528 (4) | −0.0833 (3) | 0.09085 (14) | 0.0520 (10) | |
H6 | 0.3232 | −0.1428 | 0.0815 | 0.062* | |
C7 | 0.0837 (5) | −0.1103 (3) | 0.00231 (14) | 0.0533 (10) | |
C8 | 0.1714 (6) | −0.1698 (4) | −0.04188 (16) | 0.0614 (11) | |
C9 | 0.4183 (5) | −0.0681 (3) | −0.02476 (15) | 0.0605 (11) | |
H9A | 0.5015 | −0.0370 | −0.0488 | 0.073* | |
H9B | 0.4754 | −0.1054 | 0.0049 | 0.073* | |
C10 | −0.0768 (6) | −0.1229 (4) | 0.00687 (17) | 0.0752 (13) | |
H10A | −0.1318 | −0.1681 | −0.0172 | 0.090* | |
H10B | −0.1354 | −0.0867 | 0.0342 | 0.090* | |
C11 | 0.2388 (6) | 0.0838 (3) | −0.04500 (17) | 0.0697 (13) | |
H11 | 0.3051 | 0.0950 | −0.0763 | 0.084* | |
C12 | 0.0934 (7) | 0.1263 (4) | −0.0467 (2) | 0.0993 (17) | |
H12A | 0.0209 | 0.1181 | −0.0167 | 0.119* | |
H12B | 0.0618 | 0.1649 | −0.0779 | 0.119* | |
C13 | 0.7339 (5) | 0.1295 (4) | 0.11881 (18) | 0.0651 (12) | |
C14 | 0.8013 (5) | 0.2067 (4) | 0.15872 (19) | 0.0673 (12) | |
C15 | 0.9826 (6) | 0.2296 (5) | 0.1509 (2) | 0.0993 (17) | |
H15A | 1.0487 | 0.1723 | 0.1649 | 0.119* | |
H15B | 1.0072 | 0.2392 | 0.1114 | 0.119* | |
C16 | 1.1194 (9) | 0.3922 (7) | 0.1639 (5) | 0.147 (3) | |
C17 | 1.1391 (9) | 0.4828 (5) | 0.1996 (4) | 0.170 (4) | |
H17A | 1.1743 | 0.5408 | 0.1774 | 0.255* | |
H17B | 1.2205 | 0.4685 | 0.2279 | 0.255* | |
H17C | 1.0354 | 0.4988 | 0.2172 | 0.255* | |
C18 | 0.7101 (7) | 0.2511 (5) | 0.1958 (2) | 0.121 (2) | |
H18A | 0.5982 | 0.2350 | 0.1982 | 0.145* | |
H18B | 0.7560 | 0.2994 | 0.2204 | 0.145* | |
C19 | 0.4114 (5) | −0.0433 (3) | 0.18111 (15) | 0.0552 (10) | |
C20 | 0.3722 (6) | 0.0225 (4) | 0.23068 (17) | 0.0681 (12) | |
C21 | 0.4309 (8) | 0.0571 (5) | 0.32603 (17) | 0.119 (2) | |
H21A | 0.4315 | 0.1296 | 0.3166 | 0.178* | |
H21B | 0.5178 | 0.0430 | 0.3524 | 0.178* | |
H21C | 0.3263 | 0.0393 | 0.3425 | 0.178* | |
C22 | 0.4987 (5) | −0.1292 (4) | 0.18622 (16) | 0.0747 (13) | |
H22A | 0.5371 | −0.1497 | 0.2213 | 0.090* | |
H22B | 0.5219 | −0.1694 | 0.1547 | 0.090* | |
C23 | 0.0956 (6) | −0.2190 (4) | 0.13534 (17) | 0.0693 (13) | |
C24 | −0.0544 (6) | −0.2346 (4) | 0.17112 (19) | 0.0919 (16) | |
H24A | −0.1518 | −0.2195 | 0.1496 | 0.138* | |
H24B | −0.0493 | −0.1891 | 0.2030 | 0.138* | |
H24C | −0.0583 | −0.3054 | 0.1837 | 0.138* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0704 (18) | 0.076 (2) | 0.0580 (16) | −0.0033 (18) | 0.0077 (15) | −0.0189 (16) |
O2 | 0.086 (2) | 0.077 (2) | 0.0759 (19) | −0.0053 (19) | −0.0080 (18) | −0.0257 (18) |
O3 | 0.0558 (17) | 0.0673 (19) | 0.0674 (16) | −0.0076 (15) | 0.0055 (14) | −0.0185 (16) |
O4 | 0.123 (3) | 0.131 (4) | 0.135 (3) | −0.052 (3) | 0.009 (3) | −0.023 (3) |
O5 | 0.070 (2) | 0.114 (3) | 0.128 (3) | −0.009 (2) | 0.018 (2) | −0.057 (3) |
O6 | 0.304 (10) | 0.314 (11) | 0.333 (11) | −0.168 (9) | 0.170 (9) | −0.089 (9) |
O7 | 0.106 (2) | 0.099 (3) | 0.0481 (15) | 0.021 (2) | −0.0066 (17) | −0.0103 (17) |
O8 | 0.156 (3) | 0.140 (3) | 0.0670 (19) | 0.087 (3) | −0.014 (2) | −0.026 (2) |
O9 | 0.0614 (16) | 0.065 (2) | 0.0523 (14) | −0.0042 (15) | 0.0101 (14) | 0.0005 (15) |
O10 | 0.097 (2) | 0.062 (2) | 0.139 (3) | −0.003 (2) | 0.025 (2) | 0.015 (2) |
C1 | 0.060 (2) | 0.047 (2) | 0.051 (2) | −0.001 (2) | 0.004 (2) | −0.007 (2) |
C2 | 0.070 (3) | 0.055 (3) | 0.045 (2) | −0.001 (2) | −0.001 (2) | 0.000 (2) |
C3 | 0.068 (3) | 0.059 (3) | 0.060 (2) | −0.012 (2) | 0.006 (2) | 0.001 (2) |
C4 | 0.065 (3) | 0.056 (3) | 0.055 (2) | −0.005 (2) | 0.003 (2) | −0.017 (2) |
C5 | 0.061 (2) | 0.049 (2) | 0.047 (2) | 0.000 (2) | −0.0008 (19) | −0.002 (2) |
C6 | 0.052 (2) | 0.057 (3) | 0.047 (2) | −0.003 (2) | 0.0080 (19) | −0.002 (2) |
C7 | 0.060 (3) | 0.050 (3) | 0.050 (2) | 0.000 (2) | 0.001 (2) | −0.002 (2) |
C8 | 0.075 (3) | 0.056 (3) | 0.054 (2) | 0.004 (3) | −0.012 (2) | 0.001 (2) |
C9 | 0.066 (3) | 0.065 (3) | 0.051 (2) | −0.007 (2) | 0.012 (2) | −0.004 (2) |
C10 | 0.068 (3) | 0.075 (3) | 0.083 (3) | −0.005 (3) | 0.002 (3) | −0.020 (3) |
C11 | 0.088 (3) | 0.064 (3) | 0.057 (3) | −0.002 (3) | 0.001 (2) | 0.009 (2) |
C12 | 0.122 (5) | 0.085 (4) | 0.091 (4) | 0.018 (4) | −0.001 (3) | 0.022 (3) |
C13 | 0.063 (3) | 0.067 (3) | 0.066 (3) | 0.002 (3) | 0.001 (2) | −0.010 (3) |
C14 | 0.060 (3) | 0.069 (3) | 0.073 (3) | −0.003 (3) | −0.005 (2) | −0.006 (3) |
C15 | 0.082 (3) | 0.103 (4) | 0.113 (4) | −0.010 (3) | −0.007 (3) | −0.029 (4) |
C16 | 0.111 (5) | 0.104 (6) | 0.225 (10) | −0.043 (5) | 0.038 (6) | 0.011 (7) |
C17 | 0.165 (7) | 0.086 (5) | 0.259 (10) | −0.040 (5) | −0.073 (7) | 0.017 (6) |
C18 | 0.083 (4) | 0.155 (6) | 0.124 (4) | −0.024 (4) | 0.013 (4) | −0.072 (4) |
C19 | 0.056 (2) | 0.058 (3) | 0.052 (2) | 0.002 (2) | −0.001 (2) | −0.004 (2) |
C20 | 0.075 (3) | 0.076 (3) | 0.053 (3) | 0.009 (3) | 0.006 (3) | −0.004 (3) |
C21 | 0.168 (6) | 0.138 (5) | 0.051 (3) | 0.043 (5) | −0.002 (3) | −0.026 (3) |
C22 | 0.086 (3) | 0.085 (4) | 0.053 (2) | 0.016 (3) | −0.007 (2) | −0.010 (2) |
C23 | 0.070 (3) | 0.071 (4) | 0.067 (3) | −0.017 (3) | −0.002 (3) | 0.008 (3) |
C24 | 0.088 (3) | 0.113 (4) | 0.075 (3) | −0.032 (3) | 0.016 (3) | 0.005 (3) |
O1—C8 | 1.331 (5) | C7—C8 | 1.483 (5) |
O1—C9 | 1.447 (5) | C9—H9A | 0.9700 |
O2—C8 | 1.219 (4) | C9—H9B | 0.9700 |
O3—C13 | 1.335 (5) | C10—H10A | 0.9300 |
O3—C4 | 1.467 (4) | C10—H10B | 0.9300 |
O4—C16 | 1.276 (7) | C11—C12 | 1.298 (6) |
O4—C15 | 1.442 (6) | C11—H11 | 0.9300 |
O5—C13 | 1.192 (5) | C12—H12A | 0.9300 |
O6—C16 | 1.207 (10) | C12—H12B | 0.9300 |
O7—C20 | 1.316 (5) | C13—C14 | 1.479 (6) |
O7—C21 | 1.449 (5) | C14—C18 | 1.286 (6) |
O8—C20 | 1.181 (5) | C14—C15 | 1.507 (6) |
O9—C23 | 1.361 (5) | C15—H15A | 0.9700 |
O9—C6 | 1.443 (4) | C15—H15B | 0.9700 |
O10—C23 | 1.175 (5) | C16—C17 | 1.453 (11) |
C1—C7 | 1.522 (5) | C17—H17A | 0.9600 |
C1—C6 | 1.526 (5) | C17—H17B | 0.9600 |
C1—C2 | 1.531 (5) | C17—H17C | 0.9600 |
C1—H1 | 0.9800 | C18—H18A | 0.9300 |
C2—C9 | 1.517 (5) | C18—H18B | 0.9300 |
C2—C11 | 1.528 (6) | C19—C22 | 1.319 (6) |
C2—C3 | 1.536 (5) | C19—C20 | 1.487 (6) |
C3—C4 | 1.523 (5) | C21—H21A | 0.9600 |
C3—H3A | 0.9700 | C21—H21B | 0.9600 |
C3—H3B | 0.9700 | C21—H21C | 0.9600 |
C4—C5 | 1.518 (5) | C22—H22A | 0.9300 |
C4—H4 | 0.9800 | C22—H22B | 0.9300 |
C5—C19 | 1.510 (5) | C23—C24 | 1.497 (6) |
C5—C6 | 1.527 (5) | C24—H24A | 0.9600 |
C5—H5 | 0.9800 | C24—H24B | 0.9600 |
C6—H6 | 0.9800 | C24—H24C | 0.9600 |
C7—C10 | 1.313 (6) | ||
C8—O1—C9 | 121.4 (3) | H10A—C10—H10B | 120.0 |
C13—O3—C4 | 117.9 (3) | C12—C11—C2 | 128.8 (4) |
C16—O4—C15 | 122.9 (6) | C12—C11—H11 | 115.6 |
C20—O7—C21 | 117.4 (4) | C2—C11—H11 | 115.6 |
C23—O9—C6 | 118.2 (3) | C11—C12—H12A | 120.0 |
C7—C1—C6 | 112.8 (3) | C11—C12—H12B | 120.0 |
C7—C1—C2 | 109.9 (3) | H12A—C12—H12B | 120.0 |
C6—C1—C2 | 112.9 (3) | O5—C13—O3 | 124.4 (4) |
C7—C1—H1 | 107.0 | O5—C13—C14 | 123.2 (4) |
C6—C1—H1 | 107.0 | O3—C13—C14 | 112.5 (4) |
C2—C1—H1 | 107.0 | C18—C14—C13 | 122.0 (4) |
C9—C2—C11 | 109.3 (3) | C18—C14—C15 | 123.8 (5) |
C9—C2—C1 | 107.3 (3) | C13—C14—C15 | 114.2 (4) |
C11—C2—C1 | 111.4 (3) | O4—C15—C14 | 107.5 (5) |
C9—C2—C3 | 109.8 (3) | O4—C15—H15A | 110.2 |
C11—C2—C3 | 107.5 (3) | C14—C15—H15A | 110.2 |
C1—C2—C3 | 111.6 (3) | O4—C15—H15B | 110.2 |
C4—C3—C2 | 112.7 (3) | C14—C15—H15B | 110.2 |
C4—C3—H3A | 109.0 | H15A—C15—H15B | 108.5 |
C2—C3—H3A | 109.0 | O6—C16—O4 | 115.2 (9) |
C4—C3—H3B | 109.0 | O6—C16—C17 | 128.8 (8) |
C2—C3—H3B | 109.0 | O4—C16—C17 | 115.7 (9) |
H3A—C3—H3B | 107.8 | C16—C17—H17A | 109.5 |
O3—C4—C5 | 105.0 (3) | C16—C17—H17B | 109.5 |
O3—C4—C3 | 108.4 (3) | H17A—C17—H17B | 109.5 |
C5—C4—C3 | 111.4 (3) | C16—C17—H17C | 109.5 |
O3—C4—H4 | 110.6 | H17A—C17—H17C | 109.5 |
C5—C4—H4 | 110.6 | H17B—C17—H17C | 109.5 |
C3—C4—H4 | 110.6 | C14—C18—H18A | 120.0 |
C19—C5—C4 | 110.9 (3) | C14—C18—H18B | 120.0 |
C19—C5—C6 | 114.6 (3) | H18A—C18—H18B | 120.0 |
C4—C5—C6 | 108.4 (3) | C22—C19—C20 | 121.2 (4) |
C19—C5—H5 | 107.6 | C22—C19—C5 | 123.0 (4) |
C4—C5—H5 | 107.6 | C20—C19—C5 | 115.8 (4) |
C6—C5—H5 | 107.6 | O8—C20—O7 | 123.1 (4) |
O9—C6—C1 | 107.7 (3) | O8—C20—C19 | 124.0 (4) |
O9—C6—C5 | 106.4 (3) | O7—C20—C19 | 112.9 (4) |
C1—C6—C5 | 110.9 (3) | O7—C21—H21A | 109.5 |
O9—C6—H6 | 110.6 | O7—C21—H21B | 109.5 |
C1—C6—H6 | 110.6 | H21A—C21—H21B | 109.5 |
C5—C6—H6 | 110.6 | O7—C21—H21C | 109.5 |
C10—C7—C8 | 117.9 (4) | H21A—C21—H21C | 109.5 |
C10—C7—C1 | 123.7 (4) | H21B—C21—H21C | 109.5 |
C8—C7—C1 | 118.3 (4) | C19—C22—H22A | 120.0 |
O2—C8—O1 | 117.3 (4) | C19—C22—H22B | 120.0 |
O2—C8—C7 | 122.9 (4) | H22A—C22—H22B | 120.0 |
O1—C8—C7 | 119.7 (4) | O10—C23—O9 | 123.9 (4) |
O1—C9—C2 | 114.0 (3) | O10—C23—C24 | 126.9 (5) |
O1—C9—H9A | 108.8 | O9—C23—C24 | 109.1 (5) |
C2—C9—H9A | 108.8 | C23—C24—H24A | 109.5 |
O1—C9—H9B | 108.8 | C23—C24—H24B | 109.5 |
C2—C9—H9B | 108.8 | H24A—C24—H24B | 109.5 |
H9A—C9—H9B | 107.7 | C23—C24—H24C | 109.5 |
C7—C10—H10A | 120.0 | H24A—C24—H24C | 109.5 |
C7—C10—H10B | 120.0 | H24B—C24—H24C | 109.5 |
C7—C1—C2—C9 | −55.3 (4) | C1—C7—C8—O2 | 169.9 (3) |
C6—C1—C2—C9 | 71.5 (4) | C10—C7—C8—O1 | 163.4 (4) |
C7—C1—C2—C11 | 64.2 (4) | C1—C7—C8—O1 | −13.4 (5) |
C6—C1—C2—C11 | −169.0 (3) | C8—O1—C9—C2 | −36.3 (5) |
C7—C1—C2—C3 | −175.6 (3) | C11—C2—C9—O1 | −64.0 (4) |
C6—C1—C2—C3 | −48.8 (4) | C1—C2—C9—O1 | 56.8 (4) |
C9—C2—C3—C4 | −70.3 (4) | C3—C2—C9—O1 | 178.3 (3) |
C11—C2—C3—C4 | 170.9 (3) | C9—C2—C11—C12 | 142.4 (5) |
C1—C2—C3—C4 | 48.6 (5) | C1—C2—C11—C12 | 24.1 (7) |
C13—O3—C4—C5 | 148.3 (4) | C3—C2—C11—C12 | −98.4 (6) |
C13—O3—C4—C3 | −92.6 (4) | C4—O3—C13—O5 | 3.7 (6) |
C2—C3—C4—O3 | −170.4 (3) | C4—O3—C13—C14 | −176.5 (3) |
C2—C3—C4—C5 | −55.4 (4) | O5—C13—C14—C18 | −177.6 (5) |
O3—C4—C5—C19 | −56.0 (4) | O3—C13—C14—C18 | 2.6 (6) |
C3—C4—C5—C19 | −173.1 (3) | O5—C13—C14—C15 | 3.7 (7) |
O3—C4—C5—C6 | 177.4 (3) | O3—C13—C14—C15 | −176.0 (4) |
C3—C4—C5—C6 | 60.3 (4) | C16—O4—C15—C14 | −142.1 (6) |
C23—O9—C6—C1 | 115.9 (4) | C18—C14—C15—O4 | −13.3 (8) |
C23—O9—C6—C5 | −125.1 (3) | C13—C14—C15—O4 | 165.3 (4) |
C7—C1—C6—O9 | −63.1 (4) | C15—O4—C16—O6 | −7.2 (13) |
C2—C1—C6—O9 | 171.6 (3) | C15—O4—C16—C17 | 178.6 (6) |
C7—C1—C6—C5 | −179.1 (3) | C4—C5—C19—C22 | −70.9 (5) |
C2—C1—C6—C5 | 55.6 (4) | C6—C5—C19—C22 | 52.2 (5) |
C19—C5—C6—O9 | 58.5 (4) | C4—C5—C19—C20 | 107.4 (4) |
C4—C5—C6—O9 | −177.1 (3) | C6—C5—C19—C20 | −129.5 (4) |
C19—C5—C6—C1 | 175.4 (3) | C21—O7—C20—O8 | −1.0 (7) |
C4—C5—C6—C1 | −60.2 (4) | C21—O7—C20—C19 | 178.4 (4) |
C6—C1—C7—C10 | 92.4 (5) | C22—C19—C20—O8 | −169.4 (5) |
C2—C1—C7—C10 | −140.8 (4) | C5—C19—C20—O8 | 12.3 (7) |
C6—C1—C7—C8 | −91.0 (4) | C22—C19—C20—O7 | 11.3 (6) |
C2—C1—C7—C8 | 35.8 (5) | C5—C19—C20—O7 | −167.1 (4) |
C9—O1—C8—O2 | −170.2 (3) | C6—O9—C23—O10 | −1.5 (6) |
C9—O1—C8—C7 | 13.0 (5) | C6—O9—C23—C24 | −179.6 (3) |
C10—C7—C8—O2 | −13.3 (6) |
Experimental details
Crystal data | |
Chemical formula | C24H28O10 |
Mr | 476.46 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 291 |
a, b, c (Å) | 8.0887 (2), 12.8750 (4), 23.8205 (8) |
V (Å3) | 2480.71 (13) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.20 × 0.05 × 0.05 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14723, 2589, 1373 |
Rint | 0.069 |
(sin θ/λ)max (Å−1) | 0.602 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.115, 0.87 |
No. of reflections | 2589 |
No. of parameters | 311 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.14 |
Computer programs: COLLECT (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), DENZO and SCALEPACK, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1991), SHELXL97, PARST95 (Nardelli, 1995) and PLATON (Spek, 2001).
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