The crystal structure of a peracetylated glucosyl ester of kaurenic acid, (4α)-kaur-16-en-18-carbonyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside, C34H48O11, is reported. The synchrotron X-ray diffraction experiment showed that the glucosyl moiety adopts an α-perpendicular orientation with respect to the plane of the kaurenic acid. This conformation would allow the sugar hydroxyl groups, one unprotected, to interact with solvent or with biological membranes, enhancing its in vitro activity against murine melanoma in mice.
Supporting information
CCDC reference: 236062
Key indicators
- Single-crystal synchrotron study
- T = 173 K
- Mean (C-C) = 0.005 Å
- R factor = 0.046
- wR factor = 0.125
- Data-to-parameter ratio = 5.8
checkCIF/PLATON results
No syntax errors found
Alert level A
REFLT03_ALERT_1_A Reflection count < 85% complete (theta max?)
From the CIF: _diffrn_reflns_theta_max 18.08
From the CIF: _diffrn_reflns_theta_full 0.00
From the CIF: _reflns_number_total 2336
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 3056
Completeness (_total/calc) 76.44%
| Author Response: ...
The compound experienced a first order irreversible
transition at temperatures under 173 K making the collection
of data difficult during the time allocated at beam line
ID11, ESRF. Data was collected from 1 to 19.5 degrees, but
unreliable data were discarded using the SHELX command
SHEL.
|
PLAT022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.76
| Author Response: ...
IDEM
|
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 18.08 Deg.
| Author Response: ...
IDEM
|
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.76
| Author Response: ...
IDEM
|
Alert level B
REFNR01_ALERT_3_B Ratio of reflections to parameters is < 6 for a
non-centrosymmetric structure, where ZMAX < 18
sine(theta)/lambda 0.5814
Proportion of unique data used 1.0000
Ratio reflections to parameters 5.7537
PLAT089_ALERT_3_B Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 5.75
Alert level C
THETM01_ALERT_3_C The value of sine(theta_max)/wavelength is less than 0.590
Calculated sin(theta_max)/wavelength = 0.5814
PLAT023_ALERT_3_C Resolution (too) Low [sin(th)/Lambda < 0.6]..... 18.08 Deg.
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.85 Ratio
PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.97 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.60 Ratio
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C26
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C28
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ...... C27
Alert level G
ABSMU_01 Radiation type not identified. Calculation of
_exptl_absorpt_correction_mu not performed.
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 18.08
From the CIF: _reflns_number_total 2336
Count of symmetry unique reflns 3056
Completeness (_total/calc) 76.44%
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
| Author Response: ...
The compound experienced a first order irreversible
transition at temperatures under 173 K making the collection
of data difficult during the time allocated at beam line
ID11, ESRF. Data was collected from 1 to 19.5 degrees, but
unreliable data were discarded using the SHELX command
SHEL.
|
4 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
9 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 ALERT type 2 Indicator that the structure model may be wrong or deficient
9 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Speck, 2000).
(4
α)-Kaur-16-en-18-carbonyl
2,3,4,6-tetra-
O-acetyl-
α-
D-glucopyranoside
top
Crystal data top
C34H48O11 | F(000) = 680 |
Mr = 632.72 | Dx = 1.236 Mg m−3 |
Monoclinic, P21 | Synchrotron radiation, λ = 0.53378 Å |
Hall symbol: P 2yb | Cell parameters from 1024 reflections |
a = 15.3738 (8) Å | θ = 2.4–19.3° |
b = 7.2254 (2) Å | µ = 0.06 mm−1 |
c = 15.9661 (9) Å | T = 173 K |
β = 106.578 (2)° | Needle, colourless |
V = 1699.82 (14) Å3 | 0.15 × 0.03 × 0.03 mm |
Z = 2 | |
Data collection top
Bruker fixed kappa goniometer diffractometer | 2240 reflections with I > 2σ(I) |
Radiation source: Beamline ID-11 ESRF | Rint = 0.057 |
Double crystal Si monochromator | θmax = 18.1°, θmin = 10.3° |
Detector resolution: 0.70 pixels mm-1 | h = −17→17 |
φ scan 0.1° interval | k = −7→8 |
8193 measured reflections | l = −18→18 |
2336 independent reflections | |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.125 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0866P)2 + 0.2167P] where P = (Fo2 + 2Fc2)/3 |
2336 reflections | (Δ/σ)max < 0.001 |
406 parameters | Δρmax = 0.20 e Å−3 |
1 restraint | Δρmin = −0.18 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 | |
O1 | 0.15717 (15) | 0.4151 (4) | 0.34328 (18) | 0.0517 (7) | |
O2 | 0.11242 (14) | 0.1960 (4) | 0.24137 (13) | 0.0441 (6) | |
O3 | −0.00812 (17) | 0.4872 (4) | 0.14644 (14) | 0.0479 (6) | |
O4 | 0.0774 (3) | 0.4190 (8) | 0.0582 (4) | 0.1058 (18) | |
O5 | −0.18295 (15) | 0.3512 (4) | 0.05705 (13) | 0.0440 (6) | |
O6 | −0.2517 (4) | 0.5713 (10) | 0.1126 (2) | 0.127 (3) | |
O7 | −0.25293 (15) | 0.0944 (4) | 0.16372 (15) | 0.0480 (6) | |
O8 | −0.3051 (2) | −0.0004 (8) | 0.0244 (2) | 0.0836 (12) | |
O9 | −0.05559 (18) | −0.1936 (4) | 0.35920 (15) | 0.0506 (6) | |
O10 | −0.07349 (17) | −0.4984 (4) | 0.34740 (16) | 0.0509 (6) | |
O11 | −0.00857 (14) | 0.0371 (4) | 0.24671 (14) | 0.0428 (6) | |
C1 | 0.2917 (2) | −0.1345 (5) | 0.4280 (2) | 0.0472 (8) | |
H1A | 0.2659 | −0.2257 | 0.4605 | 0.057* | |
H1B | 0.3542 | −0.1746 | 0.4315 | 0.057* | |
C2 | 0.2348 (2) | −0.1359 (5) | 0.3317 (2) | 0.0495 (8) | |
H2A | 0.2388 | −0.2594 | 0.3063 | 0.059* | |
H2B | 0.1704 | −0.1125 | 0.3281 | 0.059* | |
C3 | 0.2675 (2) | 0.0103 (6) | 0.2796 (2) | 0.0457 (8) | |
H3A | 0.2271 | 0.0101 | 0.2190 | 0.055* | |
H3B | 0.3292 | −0.0232 | 0.2773 | 0.055* | |
C4 | 0.27010 (18) | 0.2062 (5) | 0.31713 (19) | 0.0388 (7) | |
C5 | 0.32695 (16) | 0.2014 (5) | 0.41536 (18) | 0.0354 (7) | |
H5A | 0.3881 | 0.1572 | 0.4138 | 0.042* | |
C6 | 0.34584 (19) | 0.3883 (5) | 0.4613 (2) | 0.0398 (7) | |
H6A | 0.3621 | 0.4799 | 0.4221 | 0.048* | |
H6B | 0.2907 | 0.4327 | 0.4752 | 0.048* | |
C7 | 0.4232 (2) | 0.3700 (6) | 0.5449 (2) | 0.0450 (8) | |
H7A | 0.4789 | 0.3326 | 0.5298 | 0.054* | |
H7B | 0.4348 | 0.4923 | 0.5738 | 0.054* | |
C8 | 0.40454 (18) | 0.2304 (5) | 0.60854 (19) | 0.0413 (8) | |
C9 | 0.37266 (18) | 0.0446 (5) | 0.5623 (2) | 0.0407 (7) | |
H9A | 0.4270 | −0.0032 | 0.5465 | 0.049* | |
C10 | 0.29612 (18) | 0.0547 (5) | 0.47248 (19) | 0.0373 (7) | |
C11 | 0.3563 (2) | −0.0994 (6) | 0.6279 (2) | 0.0525 (9) | |
H11A | 0.3162 | −0.1978 | 0.5946 | 0.063* | |
H11B | 0.4151 | −0.1575 | 0.6584 | 0.063* | |
C12 | 0.3135 (3) | −0.0230 (7) | 0.6971 (3) | 0.0594 (11) | |
H12A | 0.2476 | −0.0047 | 0.6703 | 0.071* | |
H12B | 0.3215 | −0.1142 | 0.7450 | 0.071* | |
C13 | 0.3565 (2) | 0.1602 (7) | 0.7346 (2) | 0.0565 (10) | |
H13A | 0.3330 | 0.2048 | 0.7833 | 0.068* | |
C14 | 0.3399 (2) | 0.3006 (6) | 0.6603 (2) | 0.0460 (8) | |
H14A | 0.3559 | 0.4275 | 0.6828 | 0.055* | |
H14B | 0.2758 | 0.2986 | 0.6239 | 0.055* | |
C15 | 0.4914 (2) | 0.2005 (7) | 0.6857 (2) | 0.0549 (9) | |
H15A | 0.5298 | 0.1027 | 0.6712 | 0.066* | |
H15B | 0.5271 | 0.3163 | 0.6989 | 0.066* | |
C16 | 0.4589 (3) | 0.1429 (8) | 0.7628 (3) | 0.0596 (10) | |
C17 | 0.5094 (3) | 0.0892 (10) | 0.8405 (3) | 0.0784 (15) | |
H17A | 0.5736 | 0.0838 | 0.8525 | 0.094* | |
H17B | 0.4816 | 0.0560 | 0.8844 | 0.094* | |
C18 | 0.17505 (19) | 0.2847 (5) | 0.30522 (19) | 0.0369 (7) | |
C19 | 0.3139 (2) | 0.3340 (6) | 0.2638 (2) | 0.0491 (8) | |
H19A | 0.2771 | 0.3343 | 0.2026 | 0.074* | |
H19B | 0.3751 | 0.2894 | 0.2676 | 0.074* | |
H19C | 0.3176 | 0.4600 | 0.2873 | 0.074* | |
C20 | 0.20100 (19) | 0.0949 (5) | 0.4832 (2) | 0.0424 (7) | |
H20A | 0.1563 | 0.0994 | 0.4255 | 0.064* | |
H20B | 0.2019 | 0.2141 | 0.5127 | 0.064* | |
H20C | 0.1845 | −0.0034 | 0.5181 | 0.064* | |
C21 | 0.02061 (19) | 0.2181 (5) | 0.23823 (18) | 0.0385 (7) | |
H21A | 0.0142 | 0.2982 | 0.2872 | 0.046* | |
C22 | −0.0330 (2) | 0.2975 (5) | 0.14946 (19) | 0.0401 (7) | |
H22A | −0.0200 | 0.2262 | 0.1007 | 0.048* | |
C23 | −0.1337 (2) | 0.2897 (5) | 0.14314 (17) | 0.0393 (7) | |
H23A | −0.1465 | 0.3748 | 0.1876 | 0.047* | |
C24 | −0.1613 (2) | 0.0933 (5) | 0.15930 (18) | 0.0401 (7) | |
H24A | −0.1550 | 0.0086 | 0.1118 | 0.048* | |
C25 | −0.10006 (19) | 0.0282 (5) | 0.24883 (18) | 0.0390 (7) | |
H25A | −0.1086 | 0.1121 | 0.2957 | 0.047* | |
C26 | 0.0503 (3) | 0.5329 (8) | 0.1005 (2) | 0.0584 (11) | |
C27 | 0.0771 (4) | 0.7266 (9) | 0.1124 (3) | 0.0729 (13) | |
H27A | 0.1194 | 0.7546 | 0.0784 | 0.109* | |
H27B | 0.1067 | 0.7504 | 0.1744 | 0.109* | |
H27C | 0.0231 | 0.8051 | 0.0924 | 0.109* | |
C28 | −0.2405 (3) | 0.4936 (8) | 0.0504 (2) | 0.0666 (13) | |
C29 | −0.2843 (5) | 0.5410 (12) | −0.0429 (3) | 0.101 (2) | |
H29A | −0.3249 | 0.6471 | −0.0462 | 0.151* | |
H29B | −0.3193 | 0.4347 | −0.0726 | 0.151* | |
H29C | −0.2375 | 0.5726 | −0.0712 | 0.151* | |
C30 | −0.3190 (2) | 0.0444 (7) | 0.0906 (3) | 0.0568 (10) | |
C31 | −0.4111 (3) | 0.0675 (10) | 0.1055 (3) | 0.0777 (15) | |
H31A | −0.4584 | 0.0321 | 0.0524 | 0.116* | |
H31B | −0.4195 | 0.1970 | 0.1196 | 0.116* | |
H31C | −0.4150 | −0.0118 | 0.1541 | 0.116* | |
C32 | −0.1155 (2) | −0.1676 (6) | 0.2710 (2) | 0.0460 (8) | |
H32A | −0.1797 | −0.1874 | 0.2694 | 0.055* | |
H32B | −0.0997 | −0.2543 | 0.2296 | 0.055* | |
C33 | −0.0371 (2) | −0.3666 (5) | 0.3866 (2) | 0.0415 (7) | |
C34 | 0.0355 (3) | −0.3722 (7) | 0.4725 (2) | 0.0580 (9) | |
H34A | 0.0472 | −0.5010 | 0.4917 | 0.087* | |
H34B | 0.0155 | −0.3023 | 0.5162 | 0.087* | |
H34C | 0.0913 | −0.3169 | 0.4656 | 0.087* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0391 (11) | 0.0441 (15) | 0.0674 (14) | 0.0033 (10) | 0.0078 (9) | −0.0113 (12) |
O2 | 0.0344 (10) | 0.0580 (16) | 0.0405 (10) | −0.0010 (10) | 0.0116 (8) | −0.0094 (10) |
O3 | 0.0511 (12) | 0.0528 (16) | 0.0426 (11) | −0.0035 (10) | 0.0179 (9) | 0.0057 (10) |
O4 | 0.112 (3) | 0.119 (4) | 0.119 (3) | −0.055 (3) | 0.086 (3) | −0.042 (3) |
O5 | 0.0469 (11) | 0.0556 (16) | 0.0292 (9) | 0.0080 (10) | 0.0104 (8) | 0.0044 (9) |
O6 | 0.168 (4) | 0.173 (6) | 0.0466 (15) | 0.121 (5) | 0.042 (2) | 0.027 (2) |
O7 | 0.0357 (10) | 0.0640 (17) | 0.0409 (10) | −0.0063 (10) | 0.0052 (8) | 0.0047 (10) |
O8 | 0.0662 (17) | 0.116 (3) | 0.0536 (17) | −0.0047 (19) | −0.0072 (13) | −0.0135 (18) |
O9 | 0.0675 (15) | 0.0424 (15) | 0.0347 (11) | −0.0016 (11) | 0.0029 (9) | 0.0018 (10) |
O10 | 0.0547 (13) | 0.0492 (16) | 0.0517 (12) | −0.0019 (11) | 0.0198 (10) | −0.0001 (11) |
O11 | 0.0372 (10) | 0.0433 (14) | 0.0457 (10) | 0.0026 (9) | 0.0082 (8) | 0.0024 (9) |
C1 | 0.0415 (15) | 0.039 (2) | 0.0588 (18) | 0.0030 (13) | 0.0108 (13) | −0.0002 (15) |
C2 | 0.0503 (16) | 0.0354 (19) | 0.0601 (18) | −0.0028 (14) | 0.0113 (14) | −0.0072 (15) |
C3 | 0.0412 (14) | 0.049 (2) | 0.0495 (16) | 0.0017 (14) | 0.0174 (12) | −0.0094 (15) |
C4 | 0.0336 (13) | 0.0436 (19) | 0.0425 (15) | −0.0031 (13) | 0.0162 (11) | −0.0038 (13) |
C5 | 0.0261 (11) | 0.0400 (18) | 0.0433 (14) | 0.0000 (12) | 0.0152 (10) | −0.0024 (12) |
C6 | 0.0379 (13) | 0.0412 (18) | 0.0432 (14) | −0.0054 (12) | 0.0163 (12) | −0.0002 (13) |
C7 | 0.0355 (13) | 0.055 (2) | 0.0459 (15) | −0.0100 (13) | 0.0131 (11) | −0.0053 (15) |
C8 | 0.0303 (13) | 0.053 (2) | 0.0424 (15) | 0.0038 (13) | 0.0139 (11) | −0.0012 (14) |
C9 | 0.0306 (12) | 0.047 (2) | 0.0467 (15) | 0.0086 (12) | 0.0150 (12) | 0.0047 (13) |
C10 | 0.0286 (12) | 0.0383 (18) | 0.0459 (14) | 0.0012 (11) | 0.0120 (11) | 0.0025 (13) |
C11 | 0.0478 (16) | 0.050 (2) | 0.0583 (18) | 0.0073 (15) | 0.0129 (14) | 0.0125 (16) |
C12 | 0.0509 (17) | 0.076 (3) | 0.0551 (18) | 0.0052 (18) | 0.0210 (14) | 0.023 (2) |
C13 | 0.0468 (17) | 0.082 (3) | 0.0442 (15) | 0.0100 (18) | 0.0183 (13) | 0.0073 (18) |
C14 | 0.0381 (14) | 0.060 (2) | 0.0435 (15) | 0.0070 (15) | 0.0175 (12) | −0.0020 (14) |
C15 | 0.0358 (14) | 0.077 (3) | 0.0508 (17) | 0.0046 (17) | 0.0111 (12) | −0.0004 (18) |
C16 | 0.0510 (18) | 0.078 (3) | 0.0486 (17) | 0.0103 (18) | 0.0128 (14) | 0.0032 (18) |
C17 | 0.067 (2) | 0.108 (4) | 0.054 (2) | 0.018 (3) | 0.0065 (17) | 0.005 (2) |
C18 | 0.0360 (14) | 0.0359 (19) | 0.0392 (14) | −0.0025 (12) | 0.0113 (11) | 0.0020 (12) |
C19 | 0.0485 (16) | 0.056 (2) | 0.0484 (15) | −0.0080 (15) | 0.0224 (12) | −0.0018 (15) |
C20 | 0.0323 (13) | 0.048 (2) | 0.0508 (15) | −0.0002 (12) | 0.0174 (11) | 0.0055 (14) |
C21 | 0.0351 (13) | 0.0449 (19) | 0.0355 (13) | 0.0003 (13) | 0.0099 (10) | −0.0007 (12) |
C22 | 0.0427 (14) | 0.0437 (19) | 0.0353 (13) | 0.0006 (13) | 0.0134 (11) | 0.0008 (12) |
C23 | 0.0400 (14) | 0.051 (2) | 0.0263 (12) | 0.0009 (13) | 0.0078 (10) | 0.0013 (12) |
C24 | 0.0361 (14) | 0.050 (2) | 0.0320 (13) | −0.0015 (13) | 0.0058 (10) | −0.0003 (12) |
C25 | 0.0355 (13) | 0.048 (2) | 0.0322 (12) | −0.0030 (13) | 0.0069 (10) | −0.0002 (12) |
C26 | 0.0554 (18) | 0.087 (3) | 0.0376 (15) | −0.023 (2) | 0.0206 (14) | −0.0106 (18) |
C27 | 0.085 (3) | 0.080 (3) | 0.056 (2) | −0.032 (3) | 0.0235 (18) | 0.003 (2) |
C28 | 0.071 (2) | 0.093 (3) | 0.0394 (17) | 0.035 (2) | 0.0226 (15) | 0.017 (2) |
C29 | 0.123 (4) | 0.135 (6) | 0.0428 (19) | 0.076 (4) | 0.020 (2) | 0.025 (3) |
C30 | 0.0434 (16) | 0.065 (3) | 0.050 (2) | −0.0050 (17) | −0.0055 (14) | 0.0090 (17) |
C31 | 0.0421 (18) | 0.101 (4) | 0.079 (2) | −0.008 (2) | −0.0008 (17) | 0.020 (3) |
C32 | 0.0444 (15) | 0.053 (2) | 0.0363 (14) | −0.0050 (14) | 0.0050 (11) | 0.0008 (14) |
C33 | 0.0440 (15) | 0.044 (2) | 0.0404 (14) | −0.0038 (14) | 0.0182 (12) | 0.0015 (14) |
C34 | 0.066 (2) | 0.057 (3) | 0.0451 (16) | 0.0044 (17) | 0.0067 (14) | 0.0118 (16) |
Geometric parameters (Å, º) top
O1—C18 | 1.195 (4) | C12—C13 | 1.523 (8) |
O2—C18 | 1.348 (4) | C12—H12A | 0.9900 |
O2—C21 | 1.407 (4) | C12—H12B | 0.9900 |
O3—C26 | 1.353 (5) | C13—C16 | 1.513 (5) |
O3—C22 | 1.427 (5) | C13—C14 | 1.527 (6) |
O4—C26 | 1.211 (7) | C13—H13A | 1.0000 |
O5—C28 | 1.341 (6) | C14—H14A | 0.9900 |
O5—C23 | 1.437 (4) | C14—H14B | 0.9900 |
O6—C28 | 1.194 (6) | C15—C16 | 1.513 (5) |
O7—C30 | 1.360 (5) | C15—H15A | 0.9900 |
O7—C24 | 1.431 (4) | C15—H15B | 0.9900 |
O8—C30 | 1.180 (6) | C16—C17 | 1.321 (7) |
O9—C33 | 1.328 (5) | C17—H17A | 0.9500 |
O9—C32 | 1.459 (4) | C17—H17B | 0.9500 |
O10—C33 | 1.189 (5) | C19—H19A | 0.9800 |
O11—C21 | 1.402 (5) | C19—H19B | 0.9800 |
O11—C25 | 1.418 (4) | C19—H19C | 0.9800 |
C1—C10 | 1.533 (5) | C20—H20A | 0.9800 |
C1—C2 | 1.536 (5) | C20—H20B | 0.9800 |
C1—H1A | 0.9900 | C20—H20C | 0.9800 |
C1—H1B | 0.9900 | C21—C22 | 1.533 (4) |
C2—C3 | 1.517 (6) | C21—H21A | 1.0000 |
C2—H2A | 0.9900 | C22—C23 | 1.524 (4) |
C2—H2B | 0.9900 | C22—H22A | 1.0000 |
C3—C4 | 1.533 (5) | C23—C24 | 1.523 (5) |
C3—H3A | 0.9900 | C23—H23A | 1.0000 |
C3—H3B | 0.9900 | C24—C25 | 1.544 (4) |
C4—C18 | 1.528 (4) | C24—H24A | 1.0000 |
C4—C19 | 1.536 (5) | C25—C32 | 1.494 (6) |
C4—C5 | 1.563 (4) | C25—H25A | 1.0000 |
C5—C6 | 1.524 (5) | C26—C27 | 1.456 (8) |
C5—C10 | 1.558 (4) | C27—H27A | 0.9800 |
C5—H5A | 1.0000 | C27—H27B | 0.9800 |
C6—C7 | 1.520 (4) | C27—H27C | 0.9800 |
C6—H6A | 0.9900 | C28—C29 | 1.489 (5) |
C6—H6B | 0.9900 | C29—H29A | 0.9800 |
C7—C8 | 1.516 (5) | C29—H29B | 0.9800 |
C7—H7A | 0.9900 | C29—H29C | 0.9800 |
C7—H7B | 0.9900 | C30—C31 | 1.510 (7) |
C8—C9 | 1.543 (5) | C31—H31A | 0.9800 |
C8—C14 | 1.548 (4) | C31—H31B | 0.9800 |
C8—C15 | 1.552 (4) | C31—H31C | 0.9800 |
C9—C11 | 1.547 (5) | C32—H32A | 0.9900 |
C9—C10 | 1.576 (4) | C32—H32B | 0.9900 |
C9—H9A | 1.0000 | C33—C34 | 1.501 (5) |
C10—C20 | 1.547 (4) | C34—H34A | 0.9800 |
C11—C12 | 1.541 (6) | C34—H34B | 0.9800 |
C11—H11A | 0.9900 | C34—H34C | 0.9800 |
C11—H11B | 0.9900 | | |
| | | |
C18—O2—C21 | 117.8 (2) | H15A—C15—H15B | 108.7 |
C26—O3—C22 | 118.6 (3) | C17—C16—C15 | 127.1 (4) |
C28—O5—C23 | 117.9 (3) | C17—C16—C13 | 125.9 (4) |
C30—O7—C24 | 117.4 (3) | C15—C16—C13 | 107.0 (3) |
C33—O9—C32 | 117.2 (3) | C16—C17—H17A | 120.0 |
C21—O11—C25 | 113.0 (2) | C16—C17—H17B | 120.0 |
C10—C1—C2 | 114.0 (3) | H17A—C17—H17B | 120.0 |
C10—C1—H1A | 108.8 | O1—C18—O2 | 122.8 (3) |
C2—C1—H1A | 108.8 | O1—C18—C4 | 125.5 (3) |
C10—C1—H1B | 108.8 | O2—C18—C4 | 111.6 (3) |
C2—C1—H1B | 108.8 | C4—C19—H19A | 109.5 |
H1A—C1—H1B | 107.6 | C4—C19—H19B | 109.5 |
C3—C2—C1 | 111.1 (3) | H19A—C19—H19B | 109.5 |
C3—C2—H2A | 109.4 | C4—C19—H19C | 109.5 |
C1—C2—H2A | 109.4 | H19A—C19—H19C | 109.5 |
C3—C2—H2B | 109.4 | H19B—C19—H19C | 109.5 |
C1—C2—H2B | 109.4 | C10—C20—H20A | 109.5 |
H2A—C2—H2B | 108.0 | C10—C20—H20B | 109.5 |
C2—C3—C4 | 113.8 (3) | H20A—C20—H20B | 109.5 |
C2—C3—H3A | 108.8 | C10—C20—H20C | 109.5 |
C4—C3—H3A | 108.8 | H20A—C20—H20C | 109.5 |
C2—C3—H3B | 108.8 | H20B—C20—H20C | 109.5 |
C4—C3—H3B | 108.8 | O11—C21—O2 | 103.7 (3) |
H3A—C3—H3B | 107.7 | O11—C21—C22 | 109.6 (3) |
C18—C4—C3 | 112.2 (3) | O2—C21—C22 | 110.1 (2) |
C18—C4—C19 | 105.2 (3) | O11—C21—H21A | 111.1 |
C3—C4—C19 | 107.8 (2) | O2—C21—H21A | 111.1 |
C18—C4—C5 | 112.0 (2) | C22—C21—H21A | 111.1 |
C3—C4—C5 | 108.4 (3) | O3—C22—C23 | 108.1 (3) |
C19—C4—C5 | 111.2 (2) | O3—C22—C21 | 108.2 (3) |
C6—C5—C10 | 111.7 (2) | C23—C22—C21 | 108.4 (2) |
C6—C5—C4 | 116.0 (3) | O3—C22—H22A | 110.7 |
C10—C5—C4 | 115.2 (2) | C23—C22—H22A | 110.7 |
C6—C5—H5A | 104.1 | C21—C22—H22A | 110.7 |
C10—C5—H5A | 104.1 | O5—C23—C24 | 110.7 (3) |
C4—C5—H5A | 104.1 | O5—C23—C22 | 107.4 (2) |
C7—C6—C5 | 109.8 (3) | C24—C23—C22 | 110.5 (3) |
C7—C6—H6A | 109.7 | O5—C23—H23A | 109.4 |
C5—C6—H6A | 109.7 | C24—C23—H23A | 109.4 |
C7—C6—H6B | 109.7 | C22—C23—H23A | 109.4 |
C5—C6—H6B | 109.7 | O7—C24—C23 | 109.2 (3) |
H6A—C6—H6B | 108.2 | O7—C24—C25 | 107.7 (2) |
C8—C7—C6 | 113.3 (2) | C23—C24—C25 | 108.4 (2) |
C8—C7—H7A | 108.9 | O7—C24—H24A | 110.5 |
C6—C7—H7A | 108.9 | C23—C24—H24A | 110.5 |
C8—C7—H7B | 108.9 | C25—C24—H24A | 110.5 |
C6—C7—H7B | 108.9 | O11—C25—C32 | 105.9 (3) |
H7A—C7—H7B | 107.7 | O11—C25—C24 | 108.1 (2) |
C7—C8—C9 | 110.7 (3) | C32—C25—C24 | 114.3 (3) |
C7—C8—C14 | 114.4 (3) | O11—C25—H25A | 109.5 |
C9—C8—C14 | 112.1 (3) | C32—C25—H25A | 109.5 |
C7—C8—C15 | 109.9 (3) | C24—C25—H25A | 109.5 |
C9—C8—C15 | 110.0 (3) | O4—C26—O3 | 121.6 (5) |
C14—C8—C15 | 99.2 (2) | O4—C26—C27 | 126.7 (4) |
C8—C9—C11 | 110.6 (3) | O3—C26—C27 | 111.7 (4) |
C8—C9—C10 | 116.6 (3) | C26—C27—H27A | 109.5 |
C11—C9—C10 | 115.0 (3) | C26—C27—H27B | 109.5 |
C8—C9—H9A | 104.3 | H27A—C27—H27B | 109.5 |
C11—C9—H9A | 104.3 | C26—C27—H27C | 109.5 |
C10—C9—H9A | 104.3 | H27A—C27—H27C | 109.5 |
C1—C10—C20 | 107.5 (3) | H27B—C27—H27C | 109.5 |
C1—C10—C5 | 108.4 (2) | O6—C28—O5 | 122.9 (3) |
C20—C10—C5 | 113.1 (3) | O6—C28—C29 | 126.3 (4) |
C1—C10—C9 | 107.7 (3) | O5—C28—C29 | 110.8 (4) |
C20—C10—C9 | 113.1 (2) | C28—C29—H29A | 109.5 |
C5—C10—C9 | 106.9 (2) | C28—C29—H29B | 109.5 |
C12—C11—C9 | 115.5 (4) | H29A—C29—H29B | 109.5 |
C12—C11—H11A | 108.4 | C28—C29—H29C | 109.5 |
C9—C11—H11A | 108.4 | H29A—C29—H29C | 109.5 |
C12—C11—H11B | 108.4 | H29B—C29—H29C | 109.5 |
C9—C11—H11B | 108.4 | O8—C30—O7 | 124.0 (4) |
H11A—C11—H11B | 107.5 | O8—C30—C31 | 126.0 (3) |
C13—C12—C11 | 111.5 (3) | O7—C30—C31 | 109.8 (4) |
C13—C12—H12A | 109.3 | C30—C31—H31A | 109.5 |
C11—C12—H12A | 109.3 | C30—C31—H31B | 109.5 |
C13—C12—H12B | 109.3 | H31A—C31—H31B | 109.5 |
C11—C12—H12B | 109.3 | C30—C31—H31C | 109.5 |
H12A—C12—H12B | 108.0 | H31A—C31—H31C | 109.5 |
C16—C13—C12 | 110.1 (4) | H31B—C31—H31C | 109.5 |
C16—C13—C14 | 102.4 (3) | O9—C32—C25 | 104.6 (3) |
C12—C13—C14 | 108.3 (3) | O9—C32—H32A | 110.8 |
C16—C13—H13A | 111.9 | C25—C32—H32A | 110.8 |
C12—C13—H13A | 111.9 | O9—C32—H32B | 110.8 |
C14—C13—H13A | 111.9 | C25—C32—H32B | 110.8 |
C13—C14—C8 | 101.9 (3) | H32A—C32—H32B | 108.9 |
C13—C14—H14A | 111.4 | O10—C33—O9 | 123.8 (3) |
C8—C14—H14A | 111.4 | O10—C33—C34 | 125.1 (3) |
C13—C14—H14B | 111.4 | O9—C33—C34 | 111.1 (3) |
C8—C14—H14B | 111.4 | C33—C34—H34A | 109.5 |
H14A—C14—H14B | 109.3 | C33—C34—H34B | 109.5 |
C16—C15—C8 | 106.0 (3) | H34A—C34—H34B | 109.5 |
C16—C15—H15A | 110.5 | C33—C34—H34C | 109.5 |
C8—C15—H15A | 110.5 | H34A—C34—H34C | 109.5 |
C16—C15—H15B | 110.5 | H34B—C34—H34C | 109.5 |
C8—C15—H15B | 110.5 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13A···O6i | 1.00 | 2.54 | 3.348 (5) | 138 |
C21—H21A···O10ii | 1.00 | 2.38 | 3.281 (4) | 150 |
C27—H27C···O4iii | 0.98 | 2.59 | 3.361 (8) | 135 |
Symmetry codes: (i) −x, y−1/2, −z+1; (ii) x, y+1, z; (iii) −x, y+1/2, −z. |