A stereoisomer of bharangin triacetate [systematic name: 6,10-bis(acetyloxy)-8-isopropyl-4,4,11
a-trimethyl-2-oxo-2,3,4,6,11,11a-hexahydrobenzo[5,6]cyclohepta[1,2-
b]pyran-9-yl acetate], C
26H
32O
8, a tricyclic diterpenoid, is reported. There is a 0.56 (3):0.44 (3) disorder in the terminal isopropyl side chain. The title compound and a previously reported stereoisomer, crystallizing in the same space group, exhibit very similar molecular conformations, but differ in the orientation of one of the acetate groups, resulting in a different configuration at the atom to which the acetate group is attached. Consequently, different C—H
O interactions are observed.
Supporting information
CCDC reference: 269376
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.006 Å
- R factor = 0.060
- wR factor = 0.158
- Data-to-parameter ratio = 8.8
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.77 Ratio
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.56 Ratio
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.83 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C12
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C23
PLAT301_ALERT_3_C Main Residue Disorder ......................... 6.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 35.80 Deg.
H20B -C20 -H20A 1.555 1.555 1.555
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 24.99
From the CIF: _reflns_number_total 2719
Count of symmetry unique reflns 2718
Completeness (_total/calc) 100.04%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem
2 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
5 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
6,10-bis(acetyloxy)-8-isopropyl-4,4,11
a-trimethyl-2-oxo-2,3,4,6,11,11
a- hexahydrobenzo[5,6]cyclohepta[1,2-
b]pyran-9-yl acetate
top
Crystal data top
C26H32O8 | F(000) = 1008 |
Mr = 472.52 | Dx = 1.162 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 5772 reflections |
a = 8.1986 (5) Å | θ = 2.5–21.6° |
b = 14.0252 (9) Å | µ = 0.09 mm−1 |
c = 23.482 (1) Å | T = 273 K |
V = 2700.1 (3) Å3 | Needle, colorless |
Z = 4 | 0.27 × 0.15 × 0.10 mm |
Data collection top
CCD Area Detector diffractometer | 2554 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.032 |
Graphite monochromator | θmax = 25.0°, θmin = 1.7° |
ω scans | h = −9→9 |
19633 measured reflections | k = −16→16 |
2719 independent reflections | l = −27→27 |
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)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.158 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0888P)2 + 1.0606P] where P = (Fo2 + 2Fc2)/3 |
2719 reflections | (Δ/σ)max < 0.001 |
308 parameters | Δρmax = 0.29 e Å−3 |
44 restraints | Δρmin = −0.30 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 | Occ. (<1) |
O1 | 0.9218 (4) | 1.04915 (18) | 0.75588 (12) | 0.0521 (7) | |
O2 | 1.1214 (5) | 1.0795 (3) | 0.69701 (18) | 0.0867 (13) | |
O3 | 0.5773 (3) | 0.73497 (16) | 0.85360 (10) | 0.0368 (6) | |
O4 | 0.5227 (5) | 0.6842 (2) | 0.76589 (13) | 0.0678 (10) | |
O5 | 0.4255 (4) | 1.1151 (2) | 0.98604 (13) | 0.0595 (8) | |
O6 | 0.6763 (6) | 1.1290 (4) | 1.0202 (2) | 0.1040 (16) | |
O7 | 0.5563 (3) | 1.16213 (17) | 0.88405 (12) | 0.0466 (7) | |
O8 | 0.2926 (4) | 1.1653 (3) | 0.85900 (18) | 0.0749 (10) | |
C1 | 0.6224 (4) | 0.8274 (2) | 0.83164 (14) | 0.0321 (7) | |
H1 | 0.5567 | 0.8391 | 0.7975 | 0.039* | |
C2 | 0.7983 (4) | 0.8245 (2) | 0.81362 (15) | 0.0350 (8) | |
H2 | 0.8422 | 0.7636 | 0.8102 | 0.042* | |
C3 | 0.9003 (4) | 0.8944 (2) | 0.80185 (14) | 0.0329 (7) | |
C4 | 0.8617 (5) | 1.0004 (2) | 0.80712 (16) | 0.0362 (8) | |
C5 | 0.6791 (5) | 1.0225 (2) | 0.80508 (15) | 0.0374 (8) | |
H5A | 0.6640 | 1.0899 | 0.7976 | 0.045* | |
H5B | 0.6298 | 0.9873 | 0.7740 | 0.045* | |
C6 | 0.5940 (4) | 0.9970 (2) | 0.85961 (15) | 0.0353 (7) | |
C7 | 0.5752 (4) | 0.9014 (2) | 0.87532 (14) | 0.0357 (8) | |
C8 | 0.5082 (5) | 0.8783 (3) | 0.92742 (17) | 0.0477 (10) | |
H8 | 0.4941 | 0.8144 | 0.9366 | 0.057* | |
C9 | 0.4612 (6) | 0.9469 (3) | 0.96636 (18) | 0.0570 (11) | |
C10 | 0.4766 (5) | 1.0414 (3) | 0.94995 (17) | 0.0468 (9) | |
C11 | 0.5401 (5) | 1.0649 (3) | 0.89755 (17) | 0.0427 (9) | |
C12 | 1.0706 (5) | 0.8691 (3) | 0.7793 (2) | 0.0529 (10) | |
C13 | 1.1707 (5) | 0.9602 (3) | 0.7675 (2) | 0.0578 (11) | |
H13A | 1.2090 | 0.9861 | 0.8034 | 0.069* | |
H13B | 1.2654 | 0.9437 | 0.7449 | 0.069* | |
C14 | 1.0750 (6) | 1.0338 (3) | 0.73731 (19) | 0.0549 (11) | |
C15 | 1.1612 (6) | 0.8071 (5) | 0.8217 (4) | 0.120 (3) | |
H15A | 1.1713 | 0.8405 | 0.8572 | 0.144* | |
H15B | 1.2678 | 0.7927 | 0.8071 | 0.144* | |
H15C | 1.1018 | 0.7489 | 0.8275 | 0.144* | |
C16 | 1.0529 (8) | 0.8165 (4) | 0.7221 (3) | 0.096 (2) | |
H16A | 1.1587 | 0.7975 | 0.7087 | 0.115* | |
H16B | 1.0032 | 0.8581 | 0.6947 | 0.115* | |
H16C | 0.9859 | 0.7610 | 0.7272 | 0.115* | |
C17 | 0.9363 (6) | 1.0455 (3) | 0.8599 (2) | 0.0596 (11) | |
H17A | 1.0527 | 1.0383 | 0.8588 | 0.071* | |
H17B | 0.8942 | 1.0146 | 0.8933 | 0.071* | |
H17C | 0.9091 | 1.1120 | 0.8610 | 0.071* | |
C18 | 0.5282 (5) | 0.6696 (3) | 0.81581 (17) | 0.0436 (9) | |
C19 | 0.4798 (7) | 0.5794 (3) | 0.8440 (2) | 0.0677 (14) | |
H19A | 0.4055 | 0.5452 | 0.8199 | 0.081* | |
H19B | 0.4277 | 0.5934 | 0.8796 | 0.081* | |
H19C | 0.5750 | 0.5411 | 0.8507 | 0.081* | |
C20 | 0.3911 (12) | 0.9211 (5) | 1.0237 (3) | 0.118 (2) | |
H20B | 0.3988 | 0.9751 | 1.0501 | 0.142* | 0.56 |
H20A | 0.3316 | 0.9755 | 1.0397 | 0.142* | 0.44 |
C21A | 0.289 (2) | 0.8384 (9) | 1.0268 (5) | 0.118 (2) | 0.56 |
H21A | 0.2514 | 0.8299 | 1.0652 | 0.178* | 0.56 |
H21B | 0.3492 | 0.7833 | 1.0151 | 0.178* | 0.56 |
H21C | 0.1963 | 0.8467 | 1.0021 | 0.178* | 0.56 |
C22A | 0.5460 (18) | 0.8967 (9) | 1.0620 (4) | 0.118 (2) | 0.56 |
H22A | 0.6191 | 0.9501 | 1.0623 | 0.178* | 0.56 |
H22B | 0.6009 | 0.8420 | 1.0467 | 0.178* | 0.56 |
H22C | 0.5111 | 0.8832 | 1.1002 | 0.178* | 0.56 |
C21B | 0.201 (2) | 0.9007 (12) | 1.0098 (6) | 0.118 (2) | 0.44 |
H21D | 0.1543 | 0.9552 | 0.9911 | 0.178* | 0.44 |
H21E | 0.1431 | 0.8888 | 1.0447 | 0.178* | 0.44 |
H21F | 0.1920 | 0.8460 | 0.9854 | 0.178* | 0.44 |
C22B | 0.436 (3) | 0.8315 (11) | 1.0502 (6) | 0.118 (2) | 0.44 |
H22D | 0.3819 | 0.8256 | 1.0862 | 0.178* | 0.44 |
H22E | 0.5523 | 0.8300 | 1.0560 | 0.178* | 0.44 |
H22F | 0.4050 | 0.7797 | 1.0258 | 0.178* | 0.44 |
C23 | 0.5427 (8) | 1.1553 (4) | 1.0197 (2) | 0.0705 (14) | |
C24 | 0.4707 (10) | 1.2372 (5) | 1.0523 (3) | 0.106 (2) | |
H24A | 0.5379 | 1.2510 | 1.0847 | 0.128* | |
H24B | 0.3629 | 1.2207 | 1.0648 | 0.128* | |
H24C | 0.4654 | 1.2924 | 1.0281 | 0.128* | |
C25 | 0.4162 (6) | 1.2058 (3) | 0.86569 (18) | 0.0502 (10) | |
C26 | 0.4456 (8) | 1.3102 (3) | 0.8563 (3) | 0.0751 (15) | |
H26A | 0.3430 | 1.3431 | 0.8547 | 0.090* | |
H26B | 0.5031 | 1.3192 | 0.8211 | 0.090* | |
H26C | 0.5096 | 1.3352 | 0.8871 | 0.090* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0598 (18) | 0.0363 (13) | 0.0603 (16) | 0.0041 (14) | 0.0199 (15) | 0.0112 (12) |
O2 | 0.087 (3) | 0.069 (2) | 0.104 (3) | 0.000 (2) | 0.050 (2) | 0.030 (2) |
O3 | 0.0407 (13) | 0.0292 (11) | 0.0405 (12) | −0.0042 (11) | −0.0016 (11) | −0.0015 (10) |
O4 | 0.092 (2) | 0.0614 (19) | 0.0501 (18) | −0.0311 (19) | −0.0090 (16) | −0.0103 (14) |
O5 | 0.068 (2) | 0.0526 (17) | 0.0573 (16) | 0.0086 (16) | 0.0135 (16) | −0.0184 (14) |
O6 | 0.083 (3) | 0.108 (3) | 0.121 (3) | 0.025 (3) | −0.022 (3) | −0.055 (3) |
O7 | 0.0445 (15) | 0.0285 (12) | 0.0669 (17) | −0.0004 (12) | 0.0092 (13) | −0.0066 (12) |
O8 | 0.0506 (18) | 0.0613 (19) | 0.113 (3) | −0.0035 (17) | −0.003 (2) | 0.014 (2) |
C1 | 0.0353 (17) | 0.0291 (16) | 0.0320 (16) | −0.0021 (14) | −0.0020 (14) | 0.0013 (13) |
C2 | 0.0386 (19) | 0.0261 (16) | 0.0404 (18) | 0.0033 (15) | 0.0009 (15) | −0.0037 (14) |
C3 | 0.0334 (17) | 0.0319 (16) | 0.0336 (16) | 0.0003 (15) | −0.0009 (14) | 0.0014 (14) |
C4 | 0.043 (2) | 0.0250 (16) | 0.0408 (18) | −0.0012 (15) | 0.0050 (16) | 0.0009 (14) |
C5 | 0.047 (2) | 0.0263 (16) | 0.0395 (18) | 0.0062 (15) | 0.0027 (16) | 0.0050 (15) |
C6 | 0.0326 (16) | 0.0331 (17) | 0.0401 (18) | 0.0026 (15) | 0.0004 (15) | 0.0009 (14) |
C7 | 0.0353 (18) | 0.0314 (16) | 0.0405 (18) | 0.0033 (15) | −0.0008 (16) | 0.0017 (14) |
C8 | 0.062 (3) | 0.0331 (18) | 0.048 (2) | −0.0075 (18) | 0.010 (2) | 0.0041 (16) |
C9 | 0.072 (3) | 0.051 (2) | 0.048 (2) | 0.003 (2) | 0.020 (2) | −0.0029 (18) |
C10 | 0.049 (2) | 0.044 (2) | 0.048 (2) | 0.0005 (19) | 0.0091 (18) | −0.0122 (17) |
C11 | 0.043 (2) | 0.0315 (18) | 0.054 (2) | 0.0035 (17) | 0.0015 (18) | −0.0040 (16) |
C12 | 0.037 (2) | 0.0358 (19) | 0.086 (3) | 0.0022 (18) | 0.011 (2) | 0.0053 (19) |
C13 | 0.040 (2) | 0.052 (2) | 0.081 (3) | −0.007 (2) | 0.015 (2) | 0.000 (2) |
C14 | 0.055 (3) | 0.041 (2) | 0.068 (3) | −0.010 (2) | 0.028 (2) | 0.003 (2) |
C15 | 0.033 (2) | 0.111 (5) | 0.218 (9) | 0.013 (3) | 0.010 (4) | 0.091 (6) |
C16 | 0.080 (4) | 0.070 (3) | 0.138 (5) | −0.019 (3) | 0.066 (4) | −0.042 (3) |
C17 | 0.053 (2) | 0.059 (2) | 0.067 (3) | −0.016 (2) | 0.002 (2) | −0.024 (2) |
C18 | 0.0389 (19) | 0.042 (2) | 0.050 (2) | −0.0069 (17) | 0.0011 (17) | −0.0046 (17) |
C19 | 0.090 (4) | 0.044 (2) | 0.070 (3) | −0.026 (2) | 0.012 (3) | −0.010 (2) |
C20 | 0.184 (6) | 0.100 (3) | 0.072 (3) | 0.003 (4) | 0.061 (4) | 0.020 (3) |
C21A | 0.184 (6) | 0.100 (3) | 0.072 (3) | 0.003 (4) | 0.061 (4) | 0.020 (3) |
C22A | 0.184 (6) | 0.100 (3) | 0.072 (3) | 0.003 (4) | 0.061 (4) | 0.020 (3) |
C21B | 0.184 (6) | 0.100 (3) | 0.072 (3) | 0.003 (4) | 0.061 (4) | 0.020 (3) |
C22B | 0.184 (6) | 0.100 (3) | 0.072 (3) | 0.003 (4) | 0.061 (4) | 0.020 (3) |
C23 | 0.083 (4) | 0.064 (3) | 0.064 (3) | 0.007 (3) | 0.002 (3) | −0.021 (2) |
C24 | 0.125 (6) | 0.094 (4) | 0.101 (4) | 0.021 (4) | −0.009 (4) | −0.054 (4) |
C25 | 0.053 (2) | 0.0378 (19) | 0.060 (2) | 0.010 (2) | 0.018 (2) | −0.0033 (18) |
C26 | 0.088 (4) | 0.040 (2) | 0.097 (4) | 0.009 (3) | 0.019 (3) | 0.007 (2) |
Geometric parameters (Å, º) top
O1—C14 | 1.346 (5) | C15—H15B | 0.9600 |
O1—C4 | 1.469 (4) | C15—H15C | 0.9600 |
O2—C14 | 1.205 (5) | C16—H16A | 0.9600 |
O3—C18 | 1.338 (4) | C16—H16B | 0.9600 |
O3—C1 | 1.444 (4) | C16—H16C | 0.9600 |
O4—C18 | 1.191 (5) | C17—H17A | 0.9600 |
O5—C23 | 1.366 (7) | C17—H17B | 0.9600 |
O5—C10 | 1.402 (5) | C17—H17C | 0.9600 |
O6—C23 | 1.156 (7) | C18—C19 | 1.482 (6) |
O7—C25 | 1.372 (5) | C19—H19A | 0.9600 |
O7—C11 | 1.407 (4) | C19—H19B | 0.9600 |
O8—C25 | 1.172 (5) | C19—H19C | 0.9600 |
C1—C2 | 1.504 (5) | C20—C21A | 1.435 (13) |
C1—C7 | 1.509 (5) | C20—C22B | 1.450 (14) |
C1—H1 | 0.9800 | C20—C22A | 1.593 (14) |
C2—C3 | 1.318 (5) | C20—C21B | 1.620 (16) |
C2—H2 | 0.9300 | C20—H20B | 0.9800 |
C3—C4 | 1.524 (5) | C20—H20A | 0.9800 |
C3—C12 | 1.535 (5) | C21A—H21A | 0.9600 |
C4—C17 | 1.520 (5) | C21A—H21B | 0.9600 |
C4—C5 | 1.530 (5) | C21A—H21C | 0.9600 |
C5—C6 | 1.501 (5) | C22A—H22A | 0.9600 |
C5—H5A | 0.9700 | C22A—H22B | 0.9600 |
C5—H5B | 0.9700 | C22A—H22C | 0.9600 |
C6—C11 | 1.377 (5) | C21B—H21D | 0.9600 |
C6—C7 | 1.399 (5) | C21B—H21E | 0.9600 |
C7—C8 | 1.380 (5) | C21B—H21F | 0.9600 |
C8—C9 | 1.382 (6) | C22B—H22D | 0.9600 |
C8—H8 | 0.9300 | C22B—H22E | 0.9600 |
C9—C10 | 1.386 (6) | C22B—H22F | 0.9600 |
C9—C20 | 1.508 (7) | C23—C24 | 1.501 (7) |
C10—C11 | 1.376 (6) | C24—H24A | 0.9600 |
C12—C15 | 1.516 (7) | C24—H24B | 0.9600 |
C12—C16 | 1.539 (7) | C24—H24C | 0.9600 |
C12—C13 | 1.543 (6) | C25—C26 | 1.501 (6) |
C13—C14 | 1.479 (6) | C26—H26A | 0.9600 |
C13—H13A | 0.9700 | C26—H26B | 0.9600 |
C13—H13B | 0.9700 | C26—H26C | 0.9600 |
C15—H15A | 0.9600 | | |
| | | |
C14—O1—C4 | 120.2 (3) | C4—C17—H17C | 109.5 |
C18—O3—C1 | 117.1 (3) | H17A—C17—H17C | 109.5 |
C23—O5—C10 | 116.4 (4) | H17B—C17—H17C | 109.5 |
C25—O7—C11 | 115.1 (3) | O4—C18—O3 | 123.1 (4) |
O3—C1—C2 | 108.8 (3) | O4—C18—C19 | 125.2 (4) |
O3—C1—C7 | 108.0 (3) | O3—C18—C19 | 111.7 (3) |
C2—C1—C7 | 117.1 (3) | C18—C19—H19A | 109.5 |
O3—C1—H1 | 107.5 | C18—C19—H19B | 109.5 |
C2—C1—H1 | 107.5 | H19A—C19—H19B | 109.5 |
C7—C1—H1 | 107.5 | C18—C19—H19C | 109.5 |
C3—C2—C1 | 130.3 (3) | H19A—C19—H19C | 109.5 |
C3—C2—H2 | 114.8 | H19B—C19—H19C | 109.5 |
C1—C2—H2 | 114.8 | C21A—C20—C22B | 55.1 (10) |
C2—C3—C4 | 125.2 (3) | C21A—C20—C9 | 117.5 (7) |
C2—C3—C12 | 118.5 (3) | C22B—C20—C9 | 119.5 (8) |
C4—C3—C12 | 116.3 (3) | C21A—C20—C22A | 105.4 (9) |
O1—C4—C17 | 109.8 (3) | C22B—C20—C22A | 50.8 (10) |
O1—C4—C3 | 108.5 (3) | C9—C20—C22A | 104.6 (7) |
C17—C4—C3 | 112.9 (3) | C21A—C20—C21B | 45.8 (8) |
O1—C4—C5 | 102.0 (3) | C22B—C20—C21B | 100.3 (12) |
C17—C4—C5 | 109.6 (3) | C9—C20—C21B | 103.2 (7) |
C3—C4—C5 | 113.5 (3) | C22A—C20—C21B | 147.5 (8) |
C6—C5—C4 | 112.3 (3) | C21A—C20—H20B | 129.1 |
C6—C5—H5A | 109.1 | C22B—C20—H20B | 112.4 |
C4—C5—H5A | 109.1 | C9—C20—H20B | 110.8 |
C6—C5—H5B | 109.1 | C22A—C20—H20B | 76.0 |
C4—C5—H5B | 109.1 | C21B—C20—H20B | 109.0 |
H5A—C5—H5B | 107.9 | C21A—C20—H20A | 108.5 |
C11—C6—C7 | 117.2 (3) | C22B—C20—H20A | 129.6 |
C11—C6—C5 | 122.5 (3) | C9—C20—H20A | 110.2 |
C7—C6—C5 | 120.3 (3) | C22A—C20—H20A | 110.4 |
C8—C7—C6 | 120.2 (3) | C21B—C20—H20A | 74.6 |
C8—C7—C1 | 122.9 (3) | H20B—C20—H20A | 35.8 |
C6—C7—C1 | 116.8 (3) | C20—C21A—H21A | 109.5 |
C7—C8—C9 | 122.3 (3) | C20—C21A—H21B | 109.5 |
C7—C8—H8 | 118.8 | H21A—C21A—H21B | 109.5 |
C9—C8—H8 | 118.8 | C20—C21A—H21C | 109.5 |
C8—C9—C10 | 117.1 (4) | H21A—C21A—H21C | 109.5 |
C8—C9—C20 | 122.0 (4) | H21B—C21A—H21C | 109.5 |
C10—C9—C20 | 120.8 (4) | C20—C22A—H22A | 109.5 |
C11—C10—C9 | 120.8 (3) | C20—C22A—H22B | 109.5 |
C11—C10—O5 | 118.5 (4) | H22A—C22A—H22B | 109.5 |
C9—C10—O5 | 120.7 (4) | C20—C22A—H22C | 109.5 |
C10—C11—C6 | 122.3 (3) | H22A—C22A—H22C | 109.5 |
C10—C11—O7 | 118.0 (3) | H22B—C22A—H22C | 109.5 |
C6—C11—O7 | 119.6 (3) | C20—C21B—H21D | 109.5 |
C15—C12—C3 | 110.6 (4) | C20—C21B—H21E | 109.5 |
C15—C12—C16 | 110.1 (5) | H21D—C21B—H21E | 109.5 |
C3—C12—C16 | 109.0 (4) | C20—C21B—H21F | 109.5 |
C15—C12—C13 | 109.4 (4) | H21D—C21B—H21F | 109.5 |
C3—C12—C13 | 110.7 (3) | H21E—C21B—H21F | 109.5 |
C16—C12—C13 | 106.9 (4) | C20—C22B—H22D | 109.5 |
C14—C13—C12 | 112.5 (4) | C20—C22B—H22E | 109.5 |
C14—C13—H13A | 109.1 | H22D—C22B—H22E | 109.5 |
C12—C13—H13A | 109.1 | C20—C22B—H22F | 109.5 |
C14—C13—H13B | 109.1 | H22D—C22B—H22F | 109.5 |
C12—C13—H13B | 109.1 | H22E—C22B—H22F | 109.5 |
H13A—C13—H13B | 107.8 | O6—C23—O5 | 122.7 (5) |
O2—C14—O1 | 117.7 (4) | O6—C23—C24 | 127.7 (6) |
O2—C14—C13 | 125.5 (4) | O5—C23—C24 | 109.5 (5) |
O1—C14—C13 | 116.8 (3) | C23—C24—H24A | 109.5 |
C12—C15—H15A | 109.5 | C23—C24—H24B | 109.5 |
C12—C15—H15B | 109.5 | H24A—C24—H24B | 109.5 |
H15A—C15—H15B | 109.5 | C23—C24—H24C | 109.5 |
C12—C15—H15C | 109.5 | H24A—C24—H24C | 109.5 |
H15A—C15—H15C | 109.5 | H24B—C24—H24C | 109.5 |
H15B—C15—H15C | 109.5 | O8—C25—O7 | 123.4 (4) |
C12—C16—H16A | 109.5 | O8—C25—C26 | 126.3 (5) |
C12—C16—H16B | 109.5 | O7—C25—C26 | 110.3 (4) |
H16A—C16—H16B | 109.5 | C25—C26—H26A | 109.5 |
C12—C16—H16C | 109.5 | C25—C26—H26B | 109.5 |
H16A—C16—H16C | 109.5 | H26A—C26—H26B | 109.5 |
H16B—C16—H16C | 109.5 | C25—C26—H26C | 109.5 |
C4—C17—H17A | 109.5 | H26A—C26—H26C | 109.5 |
C4—C17—H17B | 109.5 | H26B—C26—H26C | 109.5 |
H17A—C17—H17B | 109.5 | | |
| | | |
C18—O3—C1—C2 | −85.7 (4) | C9—C10—C11—C6 | −1.4 (7) |
C18—O3—C1—C7 | 146.3 (3) | O5—C10—C11—C6 | 179.6 (4) |
O3—C1—C2—C3 | −165.1 (4) | C9—C10—C11—O7 | −178.4 (4) |
C7—C1—C2—C3 | −42.4 (5) | O5—C10—C11—O7 | 2.6 (6) |
C1—C2—C3—C4 | 3.4 (6) | C7—C6—C11—C10 | 2.8 (6) |
C1—C2—C3—C12 | −174.7 (3) | C5—C6—C11—C10 | −173.5 (4) |
C14—O1—C4—C17 | 74.6 (4) | C7—C6—C11—O7 | 179.8 (3) |
C14—O1—C4—C3 | −49.2 (4) | C5—C6—C11—O7 | 3.5 (6) |
C14—O1—C4—C5 | −169.2 (3) | C25—O7—C11—C10 | −80.8 (5) |
C2—C3—C4—O1 | −135.0 (4) | C25—O7—C11—C6 | 102.1 (4) |
C12—C3—C4—O1 | 43.1 (4) | C2—C3—C12—C15 | −59.2 (6) |
C2—C3—C4—C17 | 103.0 (4) | C4—C3—C12—C15 | 122.6 (5) |
C12—C3—C4—C17 | −78.8 (4) | C2—C3—C12—C16 | 62.1 (5) |
C2—C3—C4—C5 | −22.4 (5) | C4—C3—C12—C16 | −116.2 (4) |
C12—C3—C4—C5 | 155.8 (3) | C2—C3—C12—C13 | 179.4 (4) |
O1—C4—C5—C6 | −168.3 (3) | C4—C3—C12—C13 | 1.1 (5) |
C17—C4—C5—C6 | −52.0 (4) | C15—C12—C13—C14 | −166.9 (5) |
C3—C4—C5—C6 | 75.2 (4) | C3—C12—C13—C14 | −44.7 (5) |
C4—C5—C6—C11 | 107.2 (4) | C16—C12—C13—C14 | 73.9 (5) |
C4—C5—C6—C7 | −69.0 (5) | C4—O1—C14—O2 | −175.9 (4) |
C11—C6—C7—C8 | −1.3 (5) | C4—O1—C14—C13 | 5.5 (5) |
C5—C6—C7—C8 | 175.1 (4) | C12—C13—C14—O2 | −134.5 (5) |
C11—C6—C7—C1 | 175.3 (3) | C12—C13—C14—O1 | 43.9 (6) |
C5—C6—C7—C1 | −8.3 (5) | C1—O3—C18—O4 | 1.0 (6) |
O3—C1—C7—C8 | 2.8 (5) | C1—O3—C18—C19 | −177.9 (4) |
C2—C1—C7—C8 | −120.4 (4) | C8—C9—C20—C21A | −35.7 (13) |
O3—C1—C7—C6 | −173.8 (3) | C10—C9—C20—C21A | 142.5 (10) |
C2—C1—C7—C6 | 63.1 (4) | C8—C9—C20—C22B | 27.8 (16) |
C6—C7—C8—C9 | −1.6 (6) | C10—C9—C20—C22B | −154.1 (13) |
C1—C7—C8—C9 | −178.1 (4) | C8—C9—C20—C22A | 80.7 (8) |
C7—C8—C9—C10 | 3.1 (7) | C10—C9—C20—C22A | −101.1 (8) |
C7—C8—C9—C20 | −178.7 (6) | C8—C9—C20—C21B | −82.4 (9) |
C8—C9—C10—C11 | −1.6 (7) | C10—C9—C20—C21B | 95.7 (9) |
C20—C9—C10—C11 | −179.8 (6) | C10—O5—C23—O6 | −2.2 (8) |
C8—C9—C10—O5 | 177.4 (4) | C10—O5—C23—C24 | 175.9 (5) |
C20—C9—C10—O5 | −0.8 (8) | C11—O7—C25—O8 | −3.3 (6) |
C23—O5—C10—C11 | −85.7 (5) | C11—O7—C25—C26 | 176.3 (3) |
C23—O5—C10—C9 | 95.3 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···O3 | 0.93 | 2.35 | 2.714 (5) | 103 |
C5—H5A···O7 | 0.97 | 2.43 | 2.879 (4) | 108 |
C5—H5A···O4i | 0.97 | 2.51 | 3.265 (4) | 134 |
Symmetry code: (i) −x+1, y+1/2, −z+3/2. |