The crystal structure of swietenine, C
32H
40O
9, from
Swietenia macrophylla, a plant belonging to the meliaceae family, is reported. The crystal structure is stabilized by C—H
O hydrogen bonds. A comparison of structural features with a de-tigloylated iodobenzene derivative shows that the overall conformation is not affected by substitution of the (1-methylpropyl)carbonyloxy side chain.
Supporting information
CCDC reference: 225774
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.047
- wR factor = 0.132
- Data-to-parameter ratio = 8.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.88 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.62 Ratio
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C24
PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ...... C27
PLAT410_ALERT_2_C Short Intra H...H Contact H15A .. H30 = 1.95 Ang.
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 26.02
From the CIF: _reflns_number_total 3243
Count of symmetry unique reflns 3245
Completeness (_total/calc) 99.94%
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
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 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
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 and PARST97 (Nardelli, 1995).
Crystal data top
C32H40O9 | Dx = 1.293 Mg m−3 |
Mr = 568.64 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 5750 reflections |
a = 9.866 (3) Å | θ = 1.7–26.0° |
b = 16.092 (5) Å | µ = 0.09 mm−1 |
c = 18.392 (5) Å | T = 293 K |
V = 2920.1 (14) Å3 | Prism, colourless |
Z = 4 | 0.20 × 0.20 × 0.20 mm |
F(000) = 1216 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2916 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.031 |
Graphite monochromator | θmax = 26.0°, θmin = 1.7° |
ω scans | h = −12→11 |
22610 measured reflections | k = −19→19 |
3243 independent reflections | l = −22→22 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.132 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0894P)2 + 0.282P] where P = (Fo2 + 2Fc2)/3 |
3243 reflections | (Δ/σ)max = 0.002 |
371 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
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 | 0.5337 (3) | −0.03537 (19) | −0.02650 (13) | 0.0441 (6) | |
C2 | 0.5946 (3) | 0.04724 (17) | −0.00644 (14) | 0.0446 (7) | |
H2 | 0.5939 | 0.0831 | −0.0495 | 0.054* | |
C3 | 0.7433 (3) | 0.03610 (17) | 0.01899 (14) | 0.0441 (6) | |
H3 | 0.8043 | 0.0529 | −0.0204 | 0.053* | |
C4 | 0.7762 (3) | −0.05403 (17) | 0.04130 (13) | 0.0379 (6) | |
C5 | 0.6532 (3) | −0.08533 (14) | 0.08643 (12) | 0.0312 (5) | |
H5 | 0.6349 | −0.0408 | 0.1214 | 0.037* | |
C6 | 0.6802 (3) | −0.16302 (15) | 0.13335 (14) | 0.0394 (6) | |
H6 | 0.5916 | −0.1852 | 0.1476 | 0.047* | |
C7 | 0.7577 (3) | −0.14505 (17) | 0.20308 (14) | 0.0445 (6) | |
C8 | 0.4098 (3) | 0.04169 (16) | 0.08738 (13) | 0.0377 (6) | |
C9 | 0.3968 (3) | −0.05205 (17) | 0.08052 (14) | 0.0376 (6) | |
H9 | 0.3170 | −0.0620 | 0.0500 | 0.045* | |
C10 | 0.5203 (3) | −0.09202 (16) | 0.03918 (13) | 0.0360 (6) | |
C11 | 0.3671 (3) | −0.09357 (16) | 0.15364 (14) | 0.0406 (6) | |
H11A | 0.3443 | −0.1515 | 0.1455 | 0.049* | |
H11B | 0.4480 | −0.0918 | 0.1836 | 0.049* | |
C12 | 0.2512 (3) | −0.05153 (18) | 0.19402 (15) | 0.0441 (6) | |
H12A | 0.2394 | −0.0785 | 0.2408 | 0.053* | |
H12B | 0.1682 | −0.0591 | 0.1665 | 0.053* | |
C13 | 0.2737 (3) | 0.04155 (17) | 0.20640 (13) | 0.0401 (6) | |
C14 | 0.2987 (3) | 0.08374 (18) | 0.13250 (14) | 0.0459 (7) | |
H14 | 0.2145 | 0.0783 | 0.1047 | 0.055* | |
C15 | 0.3200 (4) | 0.1771 (2) | 0.14540 (17) | 0.0584 (9) | |
H15A | 0.3553 | 0.2015 | 0.1011 | 0.070* | |
H15B | 0.2324 | 0.2023 | 0.1547 | 0.070* | |
C16 | 0.4127 (4) | 0.19899 (19) | 0.20627 (18) | 0.0563 (8) | |
C17 | 0.3999 (3) | 0.05596 (16) | 0.25376 (14) | 0.0399 (6) | |
H17 | 0.4767 | 0.0285 | 0.2300 | 0.048* | |
C18 | 0.1462 (3) | 0.0770 (2) | 0.24371 (17) | 0.0562 (8) | |
H18A | 0.1581 | 0.1355 | 0.2520 | 0.084* | |
H18B | 0.1324 | 0.0494 | 0.2894 | 0.084* | |
H18C | 0.0687 | 0.0683 | 0.2130 | 0.084* | |
C19 | 0.4851 (4) | −0.18062 (19) | 0.01481 (18) | 0.0550 (8) | |
H19A | 0.4769 | −0.2158 | 0.0567 | 0.082* | |
H19B | 0.5556 | −0.2014 | −0.0163 | 0.082* | |
H19C | 0.4008 | −0.1801 | −0.0113 | 0.082* | |
C20 | 0.3900 (3) | 0.02306 (18) | 0.32943 (14) | 0.0412 (6) | |
C21 | 0.3526 (3) | 0.0644 (2) | 0.38998 (15) | 0.0537 (8) | |
H21 | 0.3307 | 0.1206 | 0.3913 | 0.064* | |
C22 | 0.4175 (4) | −0.0594 (2) | 0.35288 (17) | 0.0569 (8) | |
H22 | 0.4479 | −0.1033 | 0.3243 | 0.068* | |
C23 | 0.3911 (4) | −0.0616 (2) | 0.42404 (19) | 0.0679 (10) | |
H23 | 0.3992 | −0.1088 | 0.4530 | 0.081* | |
C24 | 0.8123 (4) | 0.16455 (19) | 0.07162 (17) | 0.0531 (8) | |
C25 | 0.8406 (4) | 0.20876 (19) | 0.14109 (19) | 0.0552 (8) | |
C26 | 0.8040 (4) | 0.1741 (2) | 0.20399 (19) | 0.0635 (9) | |
H26 | 0.7616 | 0.1226 | 0.2012 | 0.076* | |
C27 | 0.8238 (6) | 0.2092 (3) | 0.2786 (2) | 0.0896 (14) | |
H27A | 0.7880 | 0.1712 | 0.3140 | 0.134* | |
H27B | 0.7774 | 0.2615 | 0.2823 | 0.134* | |
H27C | 0.9188 | 0.2175 | 0.2874 | 0.134* | |
C28 | 0.8051 (3) | −0.1047 (2) | −0.02888 (15) | 0.0501 (7) | |
H28A | 0.8260 | −0.1612 | −0.0161 | 0.075* | |
H28B | 0.8806 | −0.0807 | −0.0542 | 0.075* | |
H28C | 0.7266 | −0.1037 | −0.0597 | 0.075* | |
C29 | 0.9082 (3) | −0.0538 (2) | 0.08621 (17) | 0.0526 (7) | |
H29A | 0.9299 | −0.1095 | 0.1006 | 0.079* | |
H29B | 0.8961 | −0.0200 | 0.1287 | 0.079* | |
H29C | 0.9806 | −0.0316 | 0.0573 | 0.079* | |
C30 | 0.5014 (3) | 0.08449 (18) | 0.05023 (15) | 0.0472 (7) | |
H30 | 0.5088 | 0.1411 | 0.0596 | 0.057* | |
C31 | 0.7735 (5) | −0.0610 (3) | 0.30757 (18) | 0.0783 (12) | |
H31A | 0.7333 | −0.0119 | 0.3280 | 0.117* | |
H31B | 0.8690 | −0.0523 | 0.3012 | 0.117* | |
H31C | 0.7591 | −0.1071 | 0.3398 | 0.117* | |
C32 | 0.9119 (6) | 0.2903 (2) | 0.1326 (3) | 0.0864 (13) | |
H32A | 0.9263 | 0.3014 | 0.0819 | 0.130* | |
H32B | 0.9977 | 0.2882 | 0.1571 | 0.130* | |
H32C | 0.8575 | 0.3337 | 0.1533 | 0.130* | |
O1 | 0.4323 (2) | 0.14448 (12) | 0.26057 (12) | 0.0558 (6) | |
O2 | 0.7682 (3) | 0.08780 (13) | 0.08164 (11) | 0.0550 (6) | |
O3 | 0.7117 (2) | −0.07862 (12) | 0.23777 (9) | 0.0486 (5) | |
O4 | 0.8246 (5) | 0.19404 (18) | 0.01261 (15) | 0.1114 (15) | |
O5 | 0.8468 (3) | −0.18937 (16) | 0.22468 (13) | 0.0666 (7) | |
O6 | 0.3512 (3) | 0.01348 (18) | 0.44850 (11) | 0.0675 (7) | |
O7 | 0.7485 (3) | −0.22715 (13) | 0.09531 (12) | 0.0556 (6) | |
H7 | 0.8110 | −0.2448 | 0.1203 | 0.083* | |
O8 | 0.4638 (4) | 0.26602 (15) | 0.21314 (16) | 0.0834 (9) | |
O9 | 0.4902 (3) | −0.05080 (17) | −0.08602 (10) | 0.0664 (7) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0394 (14) | 0.0683 (18) | 0.0245 (11) | 0.0086 (13) | −0.0008 (11) | −0.0045 (12) |
C2 | 0.0591 (17) | 0.0468 (14) | 0.0278 (12) | 0.0062 (14) | 0.0053 (12) | 0.0100 (11) |
C3 | 0.0566 (17) | 0.0488 (14) | 0.0267 (11) | −0.0067 (13) | 0.0081 (12) | 0.0001 (11) |
C4 | 0.0366 (13) | 0.0476 (14) | 0.0296 (12) | −0.0023 (12) | 0.0014 (10) | −0.0020 (10) |
C5 | 0.0356 (12) | 0.0324 (11) | 0.0257 (10) | 0.0008 (10) | −0.0005 (10) | −0.0048 (9) |
C6 | 0.0479 (15) | 0.0334 (12) | 0.0368 (12) | 0.0034 (11) | 0.0011 (12) | −0.0021 (10) |
C7 | 0.0467 (15) | 0.0481 (15) | 0.0386 (13) | 0.0025 (13) | −0.0038 (12) | 0.0109 (12) |
C8 | 0.0438 (14) | 0.0437 (13) | 0.0257 (11) | 0.0073 (12) | −0.0026 (10) | −0.0011 (10) |
C9 | 0.0351 (12) | 0.0472 (14) | 0.0303 (12) | −0.0028 (12) | −0.0055 (10) | −0.0080 (11) |
C10 | 0.0366 (13) | 0.0409 (13) | 0.0305 (12) | −0.0035 (11) | −0.0050 (10) | −0.0076 (10) |
C11 | 0.0453 (15) | 0.0375 (12) | 0.0389 (13) | −0.0054 (12) | 0.0000 (11) | −0.0033 (11) |
C12 | 0.0375 (14) | 0.0564 (16) | 0.0385 (13) | −0.0067 (12) | 0.0021 (11) | −0.0031 (12) |
C13 | 0.0388 (13) | 0.0499 (14) | 0.0315 (12) | 0.0051 (12) | 0.0020 (11) | 0.0001 (11) |
C14 | 0.0489 (16) | 0.0539 (16) | 0.0348 (13) | 0.0128 (14) | −0.0008 (12) | 0.0018 (12) |
C15 | 0.077 (2) | 0.0490 (17) | 0.0487 (17) | 0.0192 (16) | 0.0137 (17) | 0.0086 (14) |
C16 | 0.073 (2) | 0.0405 (15) | 0.0553 (18) | 0.0041 (15) | 0.0274 (17) | −0.0012 (13) |
C17 | 0.0383 (13) | 0.0424 (13) | 0.0390 (13) | −0.0017 (12) | 0.0068 (11) | −0.0053 (11) |
C18 | 0.0424 (16) | 0.079 (2) | 0.0474 (16) | 0.0132 (16) | 0.0050 (13) | −0.0035 (15) |
C19 | 0.0572 (18) | 0.0542 (17) | 0.0534 (16) | −0.0080 (15) | −0.0041 (15) | −0.0236 (14) |
C20 | 0.0328 (13) | 0.0541 (15) | 0.0367 (13) | 0.0007 (12) | −0.0006 (11) | −0.0041 (11) |
C21 | 0.0544 (18) | 0.0683 (19) | 0.0384 (14) | 0.0124 (16) | −0.0031 (13) | −0.0072 (13) |
C22 | 0.072 (2) | 0.0524 (17) | 0.0464 (16) | 0.0050 (16) | 0.0001 (15) | 0.0007 (13) |
C23 | 0.076 (2) | 0.076 (2) | 0.0523 (18) | 0.000 (2) | −0.0095 (18) | 0.0167 (17) |
C24 | 0.062 (2) | 0.0443 (15) | 0.0531 (17) | −0.0070 (14) | 0.0030 (15) | 0.0072 (13) |
C25 | 0.0562 (18) | 0.0431 (15) | 0.0663 (19) | −0.0022 (14) | −0.0031 (17) | −0.0052 (14) |
C26 | 0.072 (2) | 0.0578 (19) | 0.0606 (19) | −0.0047 (18) | 0.0058 (18) | −0.0124 (16) |
C27 | 0.107 (4) | 0.086 (3) | 0.076 (3) | −0.001 (3) | 0.007 (3) | −0.032 (2) |
C28 | 0.0507 (17) | 0.0596 (17) | 0.0401 (14) | 0.0075 (14) | 0.0086 (13) | −0.0072 (13) |
C29 | 0.0414 (15) | 0.071 (2) | 0.0457 (15) | −0.0090 (15) | −0.0033 (13) | 0.0070 (15) |
C30 | 0.0627 (19) | 0.0415 (14) | 0.0373 (13) | 0.0094 (13) | 0.0084 (13) | 0.0047 (11) |
C31 | 0.095 (3) | 0.099 (3) | 0.0410 (16) | −0.001 (3) | −0.0233 (19) | −0.0115 (18) |
C32 | 0.103 (3) | 0.054 (2) | 0.102 (3) | −0.020 (2) | −0.018 (3) | −0.002 (2) |
O1 | 0.0683 (14) | 0.0457 (11) | 0.0533 (12) | −0.0091 (10) | 0.0015 (11) | −0.0074 (9) |
O2 | 0.0791 (16) | 0.0469 (11) | 0.0390 (10) | −0.0187 (11) | 0.0077 (11) | −0.0026 (9) |
O3 | 0.0594 (12) | 0.0560 (11) | 0.0303 (9) | 0.0054 (10) | −0.0101 (9) | −0.0034 (8) |
O4 | 0.207 (5) | 0.0634 (15) | 0.0636 (16) | −0.049 (2) | 0.009 (2) | 0.0137 (13) |
O5 | 0.0659 (15) | 0.0735 (14) | 0.0605 (13) | 0.0208 (13) | −0.0147 (12) | 0.0104 (12) |
O6 | 0.0698 (16) | 0.0986 (19) | 0.0339 (10) | 0.0142 (15) | 0.0006 (11) | −0.0016 (11) |
O7 | 0.0688 (15) | 0.0424 (10) | 0.0555 (12) | 0.0164 (10) | 0.0041 (12) | −0.0073 (9) |
O8 | 0.112 (2) | 0.0469 (13) | 0.0914 (19) | −0.0160 (14) | 0.0294 (19) | −0.0041 (13) |
O9 | 0.0636 (15) | 0.1070 (19) | 0.0285 (9) | 0.0038 (14) | −0.0113 (10) | −0.0090 (11) |
Geometric parameters (Å, º) top
C1—O9 | 1.201 (3) | C17—O1 | 1.465 (3) |
C1—C2 | 1.505 (4) | C17—C20 | 1.492 (4) |
C1—C10 | 1.519 (4) | C17—H17 | 0.9800 |
C2—C30 | 1.514 (4) | C18—H18A | 0.9600 |
C2—C3 | 1.550 (5) | C18—H18B | 0.9600 |
C2—H2 | 0.9800 | C18—H18C | 0.9600 |
C3—O2 | 1.442 (3) | C19—H19A | 0.9600 |
C3—C4 | 1.542 (4) | C19—H19B | 0.9600 |
C3—H3 | 0.9800 | C19—H19C | 0.9600 |
C4—C29 | 1.542 (4) | C20—C21 | 1.349 (4) |
C4—C28 | 1.553 (3) | C20—C22 | 1.422 (4) |
C4—C5 | 1.554 (4) | C21—O6 | 1.353 (4) |
C5—C6 | 1.542 (3) | C21—H21 | 0.9300 |
C5—C10 | 1.577 (3) | C22—C23 | 1.335 (5) |
C5—H5 | 0.9800 | C22—H22 | 0.9300 |
C6—O7 | 1.418 (3) | C23—O6 | 1.348 (5) |
C6—C7 | 1.521 (4) | C23—H23 | 0.9300 |
C6—H6 | 0.9800 | C24—O4 | 1.191 (4) |
C7—O5 | 1.200 (4) | C24—O2 | 1.323 (4) |
C7—O3 | 1.325 (3) | C24—C25 | 1.489 (5) |
C8—C30 | 1.326 (4) | C25—C26 | 1.334 (5) |
C8—C9 | 1.519 (4) | C25—C32 | 1.497 (5) |
C8—C14 | 1.532 (4) | C26—C27 | 1.497 (5) |
C9—C11 | 1.530 (4) | C26—H26 | 0.9300 |
C9—C10 | 1.574 (4) | C27—H27A | 0.9600 |
C9—H9 | 0.9800 | C27—H27B | 0.9600 |
C10—C19 | 1.534 (4) | C27—H27C | 0.9600 |
C11—C12 | 1.522 (4) | C28—H28A | 0.9600 |
C11—H11A | 0.9700 | C28—H28B | 0.9600 |
C11—H11B | 0.9700 | C28—H28C | 0.9600 |
C12—C13 | 1.531 (4) | C29—H29A | 0.9600 |
C12—H12A | 0.9700 | C29—H29B | 0.9600 |
C12—H12B | 0.9700 | C29—H29C | 0.9600 |
C13—C18 | 1.542 (4) | C30—H30 | 0.9300 |
C13—C17 | 1.537 (4) | C31—O3 | 1.449 (4) |
C13—C14 | 1.539 (4) | C31—H31A | 0.9600 |
C14—C15 | 1.535 (4) | C31—H31B | 0.9600 |
C14—H14 | 0.9800 | C31—H31C | 0.9600 |
C15—C16 | 1.488 (5) | C32—H32A | 0.9600 |
C15—H15A | 0.9700 | C32—H32B | 0.9600 |
C15—H15B | 0.9700 | C32—H32C | 0.9600 |
C16—O8 | 1.198 (4) | O7—H7 | 0.8200 |
C16—O1 | 1.343 (4) | | |
| | | |
O9—C1—C2 | 123.3 (3) | O8—C16—O1 | 116.7 (4) |
O9—C1—C10 | 124.7 (3) | O8—C16—C15 | 123.5 (3) |
C2—C1—C10 | 111.7 (2) | O1—C16—C15 | 119.5 (3) |
C1—C2—C30 | 106.0 (2) | O1—C17—C20 | 106.2 (2) |
C1—C2—C3 | 110.5 (2) | O1—C17—C13 | 111.8 (2) |
C30—C2—C3 | 114.4 (2) | C20—C17—C13 | 115.0 (2) |
C1—C2—H2 | 108.6 | O1—C17—H17 | 107.8 |
C30—C2—H2 | 108.6 | C20—C17—H17 | 107.8 |
C3—C2—H2 | 108.6 | C13—C17—H17 | 107.8 |
O2—C3—C4 | 107.1 (2) | C13—C18—H18A | 109.5 |
O2—C3—C2 | 109.6 (2) | C13—C18—H18B | 109.5 |
C4—C3—C2 | 112.8 (2) | H18A—C18—H18B | 109.5 |
O2—C3—H3 | 109.1 | C13—C18—H18C | 109.5 |
C4—C3—H3 | 109.1 | H18A—C18—H18C | 109.5 |
C2—C3—H3 | 109.1 | H18B—C18—H18C | 109.5 |
C3—C4—C29 | 108.5 (2) | C10—C19—H19A | 109.5 |
C3—C4—C28 | 108.2 (2) | C10—C19—H19B | 109.5 |
C29—C4—C28 | 107.0 (2) | H19A—C19—H19B | 109.5 |
C3—C4—C5 | 106.4 (2) | C10—C19—H19C | 109.5 |
C29—C4—C5 | 112.0 (2) | H19A—C19—H19C | 109.5 |
C28—C4—C5 | 114.6 (2) | H19B—C19—H19C | 109.5 |
C6—C5—C4 | 115.3 (2) | C21—C20—C22 | 105.2 (3) |
C6—C5—C10 | 113.3 (2) | C21—C20—C17 | 127.8 (3) |
C4—C5—C10 | 112.14 (19) | C22—C20—C17 | 127.0 (3) |
C6—C5—H5 | 104.9 | O6—C21—C20 | 111.1 (3) |
C4—C5—H5 | 104.9 | O6—C21—H21 | 124.4 |
C10—C5—H5 | 104.9 | C20—C21—H21 | 124.4 |
O7—C6—C7 | 108.4 (2) | C23—C22—C20 | 106.5 (3) |
O7—C6—C5 | 113.3 (2) | C23—C22—H22 | 126.7 |
C7—C6—C5 | 113.8 (2) | C20—C22—H22 | 126.7 |
O7—C6—H6 | 107.0 | C22—C23—O6 | 111.1 (3) |
C7—C6—H6 | 107.0 | C22—C23—H23 | 124.4 |
C5—C6—H6 | 107.0 | O6—C23—H23 | 124.4 |
O5—C7—O3 | 124.8 (3) | O4—C24—O2 | 122.2 (3) |
O5—C7—C6 | 122.3 (3) | O4—C24—C25 | 124.9 (3) |
O3—C7—C6 | 112.8 (2) | O2—C24—C25 | 112.9 (3) |
C30—C8—C9 | 122.1 (2) | C26—C25—C24 | 119.6 (3) |
C30—C8—C14 | 122.5 (2) | C26—C25—C32 | 125.7 (3) |
C9—C8—C14 | 115.0 (2) | C24—C25—C32 | 114.7 (3) |
C8—C9—C11 | 112.1 (2) | C25—C26—C27 | 127.0 (4) |
C8—C9—C10 | 112.3 (2) | C25—C26—H26 | 116.5 |
C11—C9—C10 | 113.2 (2) | C27—C26—H26 | 116.5 |
C8—C9—H9 | 106.2 | C26—C27—H27A | 109.5 |
C11—C9—H9 | 106.2 | C26—C27—H27B | 109.5 |
C10—C9—H9 | 106.2 | H27A—C27—H27B | 109.5 |
C19—C10—C1 | 110.2 (2) | C26—C27—H27C | 109.5 |
C19—C10—C9 | 110.2 (2) | H27A—C27—H27C | 109.5 |
C1—C10—C9 | 101.9 (2) | H27B—C27—H27C | 109.5 |
C19—C10—C5 | 114.4 (2) | C4—C28—H28A | 109.5 |
C1—C10—C5 | 109.0 (2) | C4—C28—H28B | 109.5 |
C9—C10—C5 | 110.48 (18) | H28A—C28—H28B | 109.5 |
C12—C11—C9 | 112.3 (2) | C4—C28—H28C | 109.5 |
C12—C11—H11A | 109.2 | H28A—C28—H28C | 109.5 |
C9—C11—H11A | 109.2 | H28B—C28—H28C | 109.5 |
C12—C11—H11B | 109.2 | C4—C29—H29A | 109.5 |
C9—C11—H11B | 109.2 | C4—C29—H29B | 109.5 |
H11A—C11—H11B | 107.9 | H29A—C29—H29B | 109.5 |
C11—C12—C13 | 113.5 (2) | C4—C29—H29C | 109.5 |
C11—C12—H12A | 108.9 | H29A—C29—H29C | 109.5 |
C13—C12—H12A | 108.9 | H29B—C29—H29C | 109.5 |
C11—C12—H12B | 108.9 | C8—C30—C2 | 124.3 (3) |
C13—C12—H12B | 108.9 | C8—C30—H30 | 117.9 |
H12A—C12—H12B | 107.7 | C2—C30—H30 | 117.9 |
C12—C13—C18 | 108.1 (2) | O3—C31—H31A | 109.5 |
C12—C13—C17 | 110.4 (2) | O3—C31—H31B | 109.5 |
C18—C13—C17 | 110.6 (2) | H31A—C31—H31B | 109.5 |
C12—C13—C14 | 108.9 (2) | O3—C31—H31C | 109.5 |
C18—C13—C14 | 111.1 (2) | H31A—C31—H31C | 109.5 |
C17—C13—C14 | 107.7 (2) | H31B—C31—H31C | 109.5 |
C15—C14—C8 | 114.7 (3) | C25—C32—H32A | 109.5 |
C15—C14—C13 | 108.5 (2) | C25—C32—H32B | 109.5 |
C8—C14—C13 | 113.5 (2) | H32A—C32—H32B | 109.5 |
C15—C14—H14 | 106.5 | C25—C32—H32C | 109.5 |
C8—C14—H14 | 106.5 | H32A—C32—H32C | 109.5 |
C13—C14—H14 | 106.5 | H32B—C32—H32C | 109.5 |
C16—C15—C14 | 115.6 (3) | C16—O1—C17 | 122.7 (2) |
C16—C15—H15A | 108.4 | C24—O2—C3 | 118.9 (2) |
C14—C15—H15A | 108.4 | C7—O3—C31 | 116.1 (3) |
C16—C15—H15B | 108.4 | C23—O6—C21 | 105.9 (2) |
C14—C15—H15B | 108.4 | C6—O7—H7 | 109.5 |
H15A—C15—H15B | 107.4 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O7—H7···O5 | 0.82 | 2.15 | 2.640 (3) | 119 |
C18—H18B···O9i | 0.96 | 2.59 | 3.435 (4) | 147 |
C21—H21···O7ii | 0.93 | 2.58 | 3.510 (4) | 174 |
C22—H22···O8iii | 0.93 | 2.38 | 3.276 (4) | 162 |
Symmetry codes: (i) −x+1/2, −y, z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+1, y−1/2, −z+1/2. |