In the crystal structure of the title compound, (4aR,5R,6S,7S,8aS)-methyl 8a-ethenyloctahydro-5-acetoxy-7-{[2-(acetoxymethyl)-1-oxo-2-propenyl]oxy}-α,4-bis(methylene)-3-oxo-1H-2-benzopyran-6-acetate, C24H28O10, the molecule has a cis configuration at the junction of the two six-membered rings and not a trans configuration as was assigned on the basis of NMR data in solution [Asaka et al. (1977). Phytochemistry, 16, 1838–1839].
Supporting information
CCDC reference: 287475
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.006 Å
- R factor = 0.043
- wR factor = 0.115
- Data-to-parameter ratio = 8.3
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT220_ALERT_2_A Large Non-Solvent O Ueq(max)/Ueq(min) ... 5.32 Ratio
| Author Response: The crystal structure was performed at room temperature and the
results are good except the high temperature factors of some O atoms.
|
PLAT242_ALERT_2_A Check Low Ueq as Compared to Neighbors for C16
| Author Response: The crystal structure was performed at room temperature and the
results are good except the high temperature factors of some O atoms.
|
Alert level B
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.11 Ratio
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.27 Ratio
| Author Response: The crystal structure was performed at room temperature and the
results are good except the high temperature factors of some O atoms.
|
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14
| Author Response: The crystal structure was performed at room temperature and the
results are good except the high temperature factors of some O atoms.
|
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C20
| Author Response: The crystal structure was performed at room temperature and the
results are good except the high temperature factors of some O atoms.
|
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 25.33
From the CIF: _reflns_number_total 2589
Count of symmetry unique reflns 2596
Completeness (_total/calc) 99.73%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
2 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
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).
(4aR,5
R,6S,7
S,8aS)-methyl 8a-ethenyloctahydro-5-acetoxy-7-{[2-(acetoxymethyl)-1-oxo-2-propenyl]oxy}-
α,4-bis(methylene)-3-oxo-1
H-2-benzopyran-6-acetate
top
Crystal data top
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 |
Data collection top
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 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)] = 0.043 | 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) |
Crystal data top
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 |
Data collection top
Nonius KappaCCD diffractometer | 1373 reflections with I > 2σ(I) |
14723 measured reflections | Rint = 0.069 |
2589 independent reflections | |
Refinement top
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 | |
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 | |
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* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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 |
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