The title compound, (+)-10,13-dioxo-2α,4aβ,6aα,6bβ,9,9,12aβ-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8aα,9,10,11,12,12a,12bα,13,14bα-eicosahydropicene-2β-carboxylic acid, C
30H
44O
4, aggregates as carboxyl-to-ketone hydrogen-bonding catemers. Hydrogen bonds progress from the carboxyl group of one molecule to the remote-ring ketone group of a translationally related neighbor in an adjoining cell connected by a common
a cell-edge [O
O = 2.766 (3) Å and O—H
O = 163°], yielding chains that extend in the [011] direction. In the crystal structure, there are also four C—H
O close contacts.
Supporting information
CCDC reference: 630050
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.004 Å
- R factor = 0.046
- wR factor = 0.113
- Data-to-parameter ratio = 11.8
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.91
| Author Response: _diffrn_measured_fraction_theta_full Low .......0.91.
(Alert level A). Even though we collected data out to 0.83 \%A,
the crystal diffracted poorly beyond 0.88 \%A resolution, where
more than 40% of the missing data lie. Larger
crystals were not obtainable, and since the crystals of this
compound are no longer available, we can only rely on the current
data set.
|
Alert level B
PLAT024_ALERT_4_B Merging of Friedel Pairs is STRONGLY Indicated . !
PLAT230_ALERT_2_B Hirshfeld Test Diff for C2 - C16 .. 7.94 su
Alert level C
PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ... 0.30
PLAT230_ALERT_2_C Hirshfeld Test Diff for C6A - C18 .. 5.35 su
PLAT412_ALERT_2_C Short Intra XH3 .. XHn H7A .. H18B .. 1.88 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7A .. O2 .. 2.66 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H17C .. O3 .. 2.64 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H21B .. O4 .. 2.69 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 1
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 67.71
From the CIF: _reflns_number_total 3702
Count of symmetry unique reflns 2259
Completeness (_total/calc) 163.88%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1443
Fraction of Friedel pairs measured 0.639
Are heavy atom types Z>Si present no
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4A = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6B = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8A = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12A = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12B = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14B = . S
1 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
8 ALERT level G = General alerts; check
7 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
7 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.
(+)-10,13-dioxo-2
α,4a
β,6a
α,6 b
β,9,9,12
aβ-heptamethyl-
1,2,3,4,4a,5,6,6a,6 b,7,8,8a
α,9,10,11,12,12
a,12
bα,13,14
bα-
eicosahydropicene-2
β-carboxylic acid
top
Crystal data top
C30H44O4 | Z = 1 |
Mr = 468.65 | F(000) = 256 |
Triclinic, P1 | Dx = 1.238 Mg m−3 |
Hall symbol: P 1 | Melting point: 598 K |
a = 6.6054 (2) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 7.2228 (2) Å | Cell parameters from 8622 reflections |
c = 14.5495 (3) Å | θ = 3.1–67.7° |
α = 90.085 (2)° | µ = 0.63 mm−1 |
β = 96.287 (2)° | T = 100 K |
γ = 114.225 (2)° | Parallelepiped, colourless |
V = 628.39 (3) Å3 | 0.28 × 0.14 × 0.09 mm |
Data collection top
Bruker SMART CCD APEX-II area-detector diffractometer | 3702 independent reflections |
Radiation source: fine-focus sealed tube | 3345 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
φ and ω scans | θmax = 67.7°, θmin = 3.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | h = −7→7 |
Tmin = 0.843, Tmax = 0.945 | k = −8→8 |
8622 measured reflections | l = −17→17 |
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)] = 0.046 | H-atom parameters constrained |
wR(F2) = 0.113 | w = 1/[σ2(Fo2) + (0.0454P)2 + 0.3681P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
3702 reflections | Δρmax = 0.29 e Å−3 |
315 parameters | Δρmin = −0.20 e Å−3 |
3 restraints | Absolute structure: Flack (1983), 1651 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.2 (3) |
Special details top
Experimental. 'crystal mounted on cryoloop using Paratone-N' |
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 | 1.0963 (6) | 0.3181 (5) | 0.8084 (2) | 0.0384 (8) | |
H1A | 0.9926 | 0.3822 | 0.7892 | 0.046* | |
H1B | 1.2383 | 0.3957 | 0.7827 | 0.046* | |
O1 | 1.2654 (4) | −0.0900 (3) | 0.13736 (15) | 0.0420 (6) | |
C2 | 1.1424 (5) | 0.3330 (5) | 0.9151 (2) | 0.0362 (8) | |
O2 | 1.0843 (4) | 0.4036 (3) | 0.47008 (14) | 0.0369 (5) | |
C3 | 0.9278 (6) | 0.1925 (5) | 0.9563 (2) | 0.0447 (9) | |
H3A | 0.9648 | 0.1871 | 1.0238 | 0.054* | |
H3B | 0.8165 | 0.2519 | 0.9472 | 0.054* | |
O3 | 1.1774 (4) | 0.6796 (4) | 0.90149 (16) | 0.0544 (7) | |
C4 | 0.8252 (6) | −0.0202 (5) | 0.9135 (2) | 0.0485 (10) | |
H4A | 0.6841 | −0.0981 | 0.9398 | 0.058* | |
H4B | 0.9279 | −0.0863 | 0.9305 | 0.058* | |
C4A | 0.7751 (5) | −0.0307 (5) | 0.8073 (2) | 0.0396 (8) | |
O4 | 1.2512 (4) | 0.5752 (4) | 1.03971 (15) | 0.0505 (7) | |
H4 | 1.2475 | 0.6838 | 1.0582 | 0.076* | |
C5 | 0.7100 (6) | −0.2479 (5) | 0.7720 (2) | 0.0445 (9) | |
H5A | 0.5730 | −0.3384 | 0.7980 | 0.053* | |
H5B | 0.8309 | −0.2902 | 0.7943 | 0.053* | |
C6 | 0.6679 (6) | −0.2742 (5) | 0.6663 (2) | 0.0414 (9) | |
H6A | 0.5336 | −0.2503 | 0.6448 | 0.050* | |
H6B | 0.6358 | −0.4164 | 0.6478 | 0.050* | |
C6A | 0.8666 (5) | −0.1293 (4) | 0.61690 (19) | 0.0277 (6) | |
C6B | 0.7869 (5) | −0.1274 (4) | 0.51001 (19) | 0.0274 (6) | |
C7 | 0.7242 (5) | −0.3363 (4) | 0.46163 (19) | 0.0289 (7) | |
H7A | 0.8391 | −0.3863 | 0.4836 | 0.035* | |
H7B | 0.5800 | −0.4330 | 0.4803 | 0.035* | |
C8 | 0.7034 (5) | −0.3363 (4) | 0.3564 (2) | 0.0313 (7) | |
H8A | 0.5794 | −0.2989 | 0.3331 | 0.038* | |
H8B | 0.6683 | −0.4745 | 0.3306 | 0.038* | |
C8A | 0.9209 (5) | −0.1856 (4) | 0.32446 (19) | 0.0287 (7) | |
H8A1 | 1.0413 | −0.2154 | 0.3603 | 0.034* | |
C9 | 0.9426 (5) | −0.2203 (4) | 0.21993 (19) | 0.0323 (7) | |
C10 | 1.1550 (5) | −0.0550 (4) | 0.19087 (18) | 0.0315 (7) | |
C11 | 1.2240 (5) | 0.1602 (4) | 0.2279 (2) | 0.0318 (7) | |
H11A | 1.1304 | 0.2196 | 0.1925 | 0.038* | |
H11B | 1.3814 | 0.2419 | 0.2180 | 0.038* | |
C12 | 1.2017 (5) | 0.1746 (4) | 0.33116 (18) | 0.0286 (7) | |
H12A | 1.2337 | 0.3170 | 0.3492 | 0.034* | |
H12B | 1.3152 | 0.1387 | 0.3673 | 0.034* | |
C12A | 0.9688 (5) | 0.0350 (4) | 0.35646 (19) | 0.0268 (7) | |
C12B | 0.9836 (5) | 0.0391 (4) | 0.46472 (18) | 0.0249 (6) | |
H12C | 1.1173 | 0.0110 | 0.4854 | 0.030* | |
C13 | 1.0356 (5) | 0.2455 (4) | 0.51112 (19) | 0.0291 (7) | |
C14 | 1.0400 (5) | 0.2501 (4) | 0.61213 (19) | 0.0308 (7) | |
H14 | 1.1003 | 0.3796 | 0.6442 | 0.037* | |
C14A | 0.9656 (5) | 0.0860 (4) | 0.66254 (19) | 0.0297 (7) | |
C14B | 0.9965 (5) | 0.1019 (5) | 0.7674 (2) | 0.0344 (7) | |
H14B | 1.1057 | 0.0426 | 0.7880 | 0.041* | |
C15 | 1.1923 (5) | 0.5472 (5) | 0.9484 (2) | 0.0373 (8) | |
C16 | 1.3405 (6) | 0.2824 (5) | 0.9505 (2) | 0.0421 (8) | |
H16A | 1.4762 | 0.3787 | 0.9270 | 0.063* | |
H16B | 1.3098 | 0.1439 | 0.9288 | 0.063* | |
H16C | 1.3620 | 0.2924 | 1.0184 | 0.063* | |
C17 | 0.5905 (6) | 0.0420 (6) | 0.7776 (2) | 0.0468 (9) | |
H17A | 0.5717 | 0.0469 | 0.7100 | 0.070* | |
H17B | 0.6323 | 0.1780 | 0.8058 | 0.070* | |
H17C | 0.4496 | −0.0525 | 0.7980 | 0.070* | |
C18 | 1.0542 (6) | −0.2055 (5) | 0.6326 (2) | 0.0417 (8) | |
H18A | 1.1874 | −0.1104 | 0.6070 | 0.062* | |
H18B | 1.0033 | −0.3402 | 0.6016 | 0.062* | |
H18C | 1.0908 | −0.2141 | 0.6991 | 0.062* | |
C19 | 0.5797 (5) | −0.0779 (5) | 0.4975 (2) | 0.0322 (7) | |
H19A | 0.5491 | −0.0520 | 0.4325 | 0.048* | |
H19B | 0.6081 | 0.0430 | 0.5365 | 0.048* | |
H19C | 0.4502 | −0.1933 | 0.5156 | 0.048* | |
C20 | 0.9524 (7) | −0.4273 (5) | 0.2079 (2) | 0.0520 (10) | |
H20A | 0.9722 | −0.4493 | 0.1436 | 0.078* | |
H20B | 0.8129 | −0.5350 | 0.2231 | 0.078* | |
H20C | 1.0785 | −0.4299 | 0.2494 | 0.078* | |
C21 | 0.7467 (6) | −0.2230 (5) | 0.1517 (2) | 0.0408 (8) | |
H21A | 0.7460 | −0.0876 | 0.1521 | 0.061* | |
H21B | 0.6056 | −0.3220 | 0.1701 | 0.061* | |
H21C | 0.7634 | −0.2611 | 0.0892 | 0.061* | |
C22 | 0.7943 (5) | 0.1076 (5) | 0.3114 (2) | 0.0315 (7) | |
H22A | 0.6464 | −0.0064 | 0.3038 | 0.047* | |
H22B | 0.8338 | 0.1591 | 0.2506 | 0.047* | |
H22C | 0.7914 | 0.2163 | 0.3509 | 0.047* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0376 (19) | 0.0403 (18) | 0.0318 (17) | 0.0094 (15) | 0.0095 (14) | −0.0001 (13) |
O1 | 0.0504 (14) | 0.0424 (12) | 0.0333 (12) | 0.0170 (11) | 0.0138 (10) | −0.0023 (9) |
C2 | 0.0300 (17) | 0.0441 (18) | 0.0280 (16) | 0.0089 (14) | 0.0041 (13) | −0.0020 (13) |
O2 | 0.0513 (14) | 0.0302 (11) | 0.0290 (10) | 0.0151 (10) | 0.0101 (10) | 0.0041 (8) |
C3 | 0.0382 (19) | 0.058 (2) | 0.0262 (15) | 0.0077 (16) | 0.0061 (14) | −0.0012 (14) |
O3 | 0.0674 (19) | 0.0524 (15) | 0.0367 (13) | 0.0191 (13) | 0.0018 (12) | 0.0014 (11) |
C4 | 0.040 (2) | 0.056 (2) | 0.0310 (17) | −0.0005 (16) | 0.0103 (15) | 0.0067 (15) |
C4A | 0.0261 (17) | 0.055 (2) | 0.0250 (15) | 0.0031 (15) | 0.0072 (13) | 0.0039 (13) |
O4 | 0.0661 (18) | 0.0614 (16) | 0.0320 (12) | 0.0359 (14) | −0.0007 (11) | −0.0104 (10) |
C5 | 0.039 (2) | 0.049 (2) | 0.0306 (17) | 0.0018 (16) | 0.0064 (15) | 0.0132 (14) |
C6 | 0.046 (2) | 0.0367 (17) | 0.0288 (16) | 0.0035 (15) | 0.0063 (15) | 0.0054 (12) |
C6A | 0.0239 (15) | 0.0341 (15) | 0.0259 (14) | 0.0130 (13) | 0.0014 (12) | 0.0038 (11) |
C6B | 0.0245 (16) | 0.0340 (14) | 0.0232 (13) | 0.0107 (12) | 0.0062 (12) | 0.0031 (11) |
C7 | 0.0259 (16) | 0.0282 (15) | 0.0303 (15) | 0.0082 (12) | 0.0059 (12) | 0.0060 (11) |
C8 | 0.0312 (17) | 0.0282 (14) | 0.0306 (15) | 0.0088 (13) | 0.0025 (12) | −0.0003 (11) |
C8A | 0.0311 (17) | 0.0271 (14) | 0.0259 (14) | 0.0102 (12) | 0.0030 (12) | 0.0023 (11) |
C9 | 0.043 (2) | 0.0281 (15) | 0.0258 (15) | 0.0134 (13) | 0.0070 (13) | −0.0006 (11) |
C10 | 0.0399 (19) | 0.0363 (16) | 0.0198 (14) | 0.0173 (14) | 0.0030 (13) | 0.0032 (11) |
C11 | 0.0366 (18) | 0.0293 (14) | 0.0265 (14) | 0.0090 (13) | 0.0100 (13) | 0.0045 (11) |
C12 | 0.0346 (17) | 0.0274 (14) | 0.0233 (14) | 0.0121 (13) | 0.0049 (13) | 0.0031 (11) |
C12A | 0.0275 (17) | 0.0296 (15) | 0.0257 (14) | 0.0136 (13) | 0.0057 (12) | 0.0017 (11) |
C12B | 0.0215 (16) | 0.0277 (14) | 0.0224 (13) | 0.0075 (12) | 0.0003 (11) | 0.0036 (11) |
C13 | 0.0261 (17) | 0.0306 (15) | 0.0294 (15) | 0.0099 (13) | 0.0056 (12) | 0.0023 (12) |
C14 | 0.0263 (17) | 0.0338 (15) | 0.0288 (15) | 0.0085 (13) | 0.0050 (12) | −0.0030 (11) |
C14A | 0.0207 (16) | 0.0407 (16) | 0.0242 (14) | 0.0088 (13) | 0.0043 (12) | 0.0027 (12) |
C14B | 0.0287 (17) | 0.0423 (17) | 0.0264 (15) | 0.0087 (14) | 0.0046 (12) | 0.0035 (12) |
C15 | 0.0293 (18) | 0.0515 (19) | 0.0287 (16) | 0.0138 (15) | 0.0047 (13) | −0.0014 (14) |
C16 | 0.057 (2) | 0.0363 (17) | 0.0324 (16) | 0.0162 (16) | 0.0149 (15) | −0.0006 (13) |
C17 | 0.0316 (18) | 0.065 (2) | 0.0332 (17) | 0.0074 (16) | 0.0126 (14) | −0.0052 (15) |
C18 | 0.054 (2) | 0.0477 (19) | 0.0301 (16) | 0.0304 (17) | −0.0035 (15) | 0.0009 (13) |
C19 | 0.0274 (16) | 0.0432 (17) | 0.0258 (14) | 0.0139 (14) | 0.0047 (12) | 0.0046 (12) |
C20 | 0.077 (3) | 0.0356 (18) | 0.045 (2) | 0.0201 (18) | 0.0277 (19) | 0.0044 (15) |
C21 | 0.0410 (19) | 0.0430 (18) | 0.0253 (15) | 0.0045 (15) | 0.0026 (13) | 0.0007 (12) |
C22 | 0.0371 (17) | 0.0339 (15) | 0.0262 (14) | 0.0173 (13) | 0.0040 (12) | 0.0052 (11) |
Geometric parameters (Å, º) top
C1—C14B | 1.515 (4) | C8A—H8A1 | 1.0000 |
C1—C2 | 1.544 (4) | C9—C10 | 1.527 (4) |
C1—H1A | 0.9900 | C9—C20 | 1.534 (4) |
C1—H1B | 0.9900 | C9—C21 | 1.536 (5) |
O1—C10 | 1.215 (3) | C10—C11 | 1.508 (4) |
C2—C15 | 1.510 (4) | C11—C12 | 1.533 (4) |
C2—C16 | 1.535 (5) | C11—H11A | 0.9900 |
C2—C3 | 1.551 (4) | C11—H11B | 0.9900 |
O2—C13 | 1.227 (3) | C12—C12A | 1.540 (4) |
C3—C4 | 1.502 (5) | C12—H12A | 0.9900 |
C3—H3A | 0.9900 | C12—H12B | 0.9900 |
C3—H3B | 0.9900 | C12A—C22 | 1.538 (4) |
O3—C15 | 1.206 (4) | C12A—C12B | 1.567 (4) |
C4—C4A | 1.540 (4) | C12B—C13 | 1.524 (4) |
C4—H4A | 0.9900 | C12B—H12C | 1.0000 |
C4—H4B | 0.9900 | C13—C14 | 1.467 (4) |
C4A—C5 | 1.519 (5) | C14—C14A | 1.337 (4) |
C4A—C17 | 1.536 (5) | C14—H14 | 0.9500 |
C4A—C14B | 1.558 (4) | C14A—C14B | 1.515 (4) |
O4—C15 | 1.334 (4) | C14B—H14B | 1.0000 |
O4—H4 | 0.8400 | C16—H16A | 0.9800 |
C5—C6 | 1.529 (4) | C16—H16B | 0.9800 |
C5—H5A | 0.9900 | C16—H16C | 0.9800 |
C5—H5B | 0.9900 | C17—H17A | 0.9800 |
C6—C6A | 1.555 (4) | C17—H17B | 0.9800 |
C6—H6A | 0.9900 | C17—H17C | 0.9800 |
C6—H6B | 0.9900 | C18—H18A | 0.9800 |
C6A—C14A | 1.534 (4) | C18—H18B | 0.9800 |
C6A—C18 | 1.545 (5) | C18—H18C | 0.9800 |
C6A—C6B | 1.588 (4) | C19—H19A | 0.9800 |
C6B—C7 | 1.538 (4) | C19—H19B | 0.9800 |
C6B—C19 | 1.543 (5) | C19—H19C | 0.9800 |
C6B—C12B | 1.574 (3) | C20—H20A | 0.9800 |
C7—C8 | 1.522 (4) | C20—H20B | 0.9800 |
C7—H7A | 0.9900 | C20—H20C | 0.9800 |
C7—H7B | 0.9900 | C21—H21A | 0.9800 |
C8—C8A | 1.526 (4) | C21—H21B | 0.9800 |
C8—H8A | 0.9900 | C21—H21C | 0.9800 |
C8—H8B | 0.9900 | C22—H22A | 0.9800 |
C8A—C12A | 1.552 (4) | C22—H22B | 0.9800 |
C8A—C9 | 1.572 (4) | C22—H22C | 0.9800 |
| | | |
C14B—C1—C2 | 113.5 (3) | C10—C11—H11A | 108.9 |
C14B—C1—H1A | 108.9 | C12—C11—H11A | 108.9 |
C2—C1—H1A | 108.9 | C10—C11—H11B | 108.9 |
C14B—C1—H1B | 108.9 | C12—C11—H11B | 108.9 |
C2—C1—H1B | 108.9 | H11A—C11—H11B | 107.8 |
H1A—C1—H1B | 107.7 | C11—C12—C12A | 113.5 (2) |
C15—C2—C16 | 109.0 (3) | C11—C12—H12A | 108.9 |
C15—C2—C1 | 108.3 (3) | C12A—C12—H12A | 108.9 |
C16—C2—C1 | 112.5 (3) | C11—C12—H12B | 108.9 |
C15—C2—C3 | 106.3 (3) | C12A—C12—H12B | 108.9 |
C16—C2—C3 | 110.9 (3) | H12A—C12—H12B | 107.7 |
C1—C2—C3 | 109.6 (3) | C22—C12A—C12 | 109.5 (2) |
C4—C3—C2 | 113.2 (3) | C22—C12A—C8A | 113.0 (2) |
C4—C3—H3A | 108.9 | C12—C12A—C8A | 107.5 (2) |
C2—C3—H3A | 108.9 | C22—C12A—C12B | 112.8 (2) |
C4—C3—H3B | 108.9 | C12—C12A—C12B | 107.4 (2) |
C2—C3—H3B | 108.9 | C8A—C12A—C12B | 106.2 (2) |
H3A—C3—H3B | 107.7 | C13—C12B—C12A | 114.9 (2) |
C3—C4—C4A | 113.8 (3) | C13—C12B—C6B | 108.4 (2) |
C3—C4—H4A | 108.8 | C12A—C12B—C6B | 118.0 (2) |
C4A—C4—H4A | 108.8 | C13—C12B—H12C | 104.6 |
C3—C4—H4B | 108.8 | C12A—C12B—H12C | 104.6 |
C4A—C4—H4B | 108.8 | C6B—C12B—H12C | 104.6 |
H4A—C4—H4B | 107.7 | O2—C13—C14 | 120.0 (3) |
C5—C4A—C17 | 111.6 (3) | O2—C13—C12B | 124.2 (2) |
C5—C4A—C4 | 108.3 (3) | C14—C13—C12B | 115.7 (2) |
C17—C4A—C4 | 110.9 (3) | C14A—C14—C13 | 125.0 (3) |
C5—C4A—C14B | 106.4 (3) | C14A—C14—H14 | 117.5 |
C17—C4A—C14B | 111.4 (3) | C13—C14—H14 | 117.5 |
C4—C4A—C14B | 108.1 (2) | C14—C14A—C14B | 122.0 (3) |
C15—O4—H4 | 109.5 | C14—C14A—C6A | 121.2 (2) |
C4A—C5—C6 | 112.9 (3) | C14B—C14A—C6A | 116.5 (2) |
C4A—C5—H5A | 109.0 | C1—C14B—C14A | 114.0 (2) |
C6—C5—H5A | 109.0 | C1—C14B—C4A | 111.5 (3) |
C4A—C5—H5B | 109.0 | C14A—C14B—C4A | 111.3 (2) |
C6—C5—H5B | 109.0 | C1—C14B—H14B | 106.5 |
H5A—C5—H5B | 107.8 | C14A—C14B—H14B | 106.5 |
C5—C6—C6A | 113.9 (3) | C4A—C14B—H14B | 106.5 |
C5—C6—H6A | 108.8 | O3—C15—O4 | 122.1 (3) |
C6A—C6—H6A | 108.8 | O3—C15—C2 | 126.4 (3) |
C5—C6—H6B | 108.8 | O4—C15—C2 | 111.5 (3) |
C6A—C6—H6B | 108.8 | C2—C16—H16A | 109.5 |
H6A—C6—H6B | 107.7 | C2—C16—H16B | 109.5 |
C14A—C6A—C18 | 105.8 (2) | H16A—C16—H16B | 109.5 |
C14A—C6A—C6 | 110.8 (2) | C2—C16—H16C | 109.5 |
C18—C6A—C6 | 107.3 (3) | H16A—C16—H16C | 109.5 |
C14A—C6A—C6B | 110.9 (2) | H16B—C16—H16C | 109.5 |
C18—C6A—C6B | 112.0 (2) | C4A—C17—H17A | 109.5 |
C6—C6A—C6B | 110.0 (2) | C4A—C17—H17B | 109.5 |
C7—C6B—C19 | 108.3 (2) | H17A—C17—H17B | 109.5 |
C7—C6B—C12B | 109.6 (2) | C4A—C17—H17C | 109.5 |
C19—C6B—C12B | 109.6 (2) | H17A—C17—H17C | 109.5 |
C7—C6B—C6A | 110.5 (2) | H17B—C17—H17C | 109.5 |
C19—C6B—C6A | 110.3 (2) | C6A—C18—H18A | 109.5 |
C12B—C6B—C6A | 108.6 (2) | C6A—C18—H18B | 109.5 |
C8—C7—C6B | 114.4 (2) | H18A—C18—H18B | 109.5 |
C8—C7—H7A | 108.7 | C6A—C18—H18C | 109.5 |
C6B—C7—H7A | 108.7 | H18A—C18—H18C | 109.5 |
C8—C7—H7B | 108.7 | H18B—C18—H18C | 109.5 |
C6B—C7—H7B | 108.7 | C6B—C19—H19A | 109.5 |
H7A—C7—H7B | 107.6 | C6B—C19—H19B | 109.5 |
C7—C8—C8A | 110.5 (2) | H19A—C19—H19B | 109.5 |
C7—C8—H8A | 109.6 | C6B—C19—H19C | 109.5 |
C8A—C8—H8A | 109.6 | H19A—C19—H19C | 109.5 |
C7—C8—H8B | 109.6 | H19B—C19—H19C | 109.5 |
C8A—C8—H8B | 109.6 | C9—C20—H20A | 109.5 |
H8A—C8—H8B | 108.1 | C9—C20—H20B | 109.5 |
C8—C8A—C12A | 110.7 (2) | H20A—C20—H20B | 109.5 |
C8—C8A—C9 | 113.9 (2) | C9—C20—H20C | 109.5 |
C12A—C8A—C9 | 116.1 (2) | H20A—C20—H20C | 109.5 |
C8—C8A—H8A1 | 105.0 | H20B—C20—H20C | 109.5 |
C12A—C8A—H8A1 | 105.0 | C9—C21—H21A | 109.5 |
C9—C8A—H8A1 | 105.0 | C9—C21—H21B | 109.5 |
C10—C9—C20 | 109.0 (3) | H21A—C21—H21B | 109.5 |
C10—C9—C21 | 106.8 (2) | C9—C21—H21C | 109.5 |
C20—C9—C21 | 107.2 (3) | H21A—C21—H21C | 109.5 |
C10—C9—C8A | 111.0 (2) | H21B—C21—H21C | 109.5 |
C20—C9—C8A | 108.2 (2) | C12A—C22—H22A | 109.5 |
C21—C9—C8A | 114.4 (3) | C12A—C22—H22B | 109.5 |
O1—C10—C11 | 119.4 (3) | H22A—C22—H22B | 109.5 |
O1—C10—C9 | 122.4 (3) | C12A—C22—H22C | 109.5 |
C11—C10—C9 | 118.2 (2) | H22A—C22—H22C | 109.5 |
C10—C11—C12 | 113.1 (2) | H22B—C22—H22C | 109.5 |
| | | |
C14B—C1—C2—C15 | −167.8 (3) | C8—C8A—C12A—C22 | −65.1 (3) |
C14B—C1—C2—C16 | 71.6 (3) | C9—C8A—C12A—C22 | 66.8 (3) |
C14B—C1—C2—C3 | −52.2 (4) | C8—C8A—C12A—C12 | 173.9 (2) |
C15—C2—C3—C4 | 167.1 (3) | C9—C8A—C12A—C12 | −54.2 (3) |
C16—C2—C3—C4 | −74.5 (4) | C8—C8A—C12A—C12B | 59.1 (3) |
C1—C2—C3—C4 | 50.3 (4) | C9—C8A—C12A—C12B | −169.0 (2) |
C2—C3—C4—C4A | −54.6 (4) | C22—C12A—C12B—C13 | −57.0 (3) |
C3—C4—C4A—C5 | 170.5 (3) | C12—C12A—C12B—C13 | 63.8 (3) |
C3—C4—C4A—C17 | −66.7 (4) | C8A—C12A—C12B—C13 | 178.7 (3) |
C3—C4—C4A—C14B | 55.7 (4) | C22—C12A—C12B—C6B | 73.0 (3) |
C17—C4A—C5—C6 | 60.6 (3) | C12—C12A—C12B—C6B | −166.2 (2) |
C4—C4A—C5—C6 | −177.1 (3) | C8A—C12A—C12B—C6B | −51.3 (3) |
C14B—C4A—C5—C6 | −61.1 (4) | C7—C6B—C12B—C13 | 177.6 (2) |
C4A—C5—C6—C6A | 55.0 (4) | C19—C6B—C12B—C13 | 58.9 (3) |
C5—C6—C6A—C14A | −42.7 (4) | C6A—C6B—C12B—C13 | −61.7 (3) |
C5—C6—C6A—C18 | 72.3 (3) | C7—C6B—C12B—C12A | 44.7 (3) |
C5—C6—C6A—C6B | −165.7 (3) | C19—C6B—C12B—C12A | −74.0 (3) |
C14A—C6A—C6B—C7 | 170.7 (3) | C6A—C6B—C12B—C12A | 165.4 (2) |
C18—C6A—C6B—C7 | 52.8 (3) | C12A—C12B—C13—O2 | −6.8 (4) |
C6—C6A—C6B—C7 | −66.3 (3) | C6B—C12B—C13—O2 | −141.4 (3) |
C14A—C6A—C6B—C19 | −69.6 (3) | C12A—C12B—C13—C14 | 177.3 (2) |
C18—C6A—C6B—C19 | 172.5 (3) | C6B—C12B—C13—C14 | 42.8 (3) |
C6—C6A—C6B—C19 | 53.4 (3) | O2—C13—C14—C14A | 171.8 (3) |
C14A—C6A—C6B—C12B | 50.6 (3) | C12B—C13—C14—C14A | −12.2 (4) |
C18—C6A—C6B—C12B | −67.3 (3) | C13—C14—C14A—C14B | 173.8 (3) |
C6—C6A—C6B—C12B | 173.5 (3) | C13—C14—C14A—C6A | 0.3 (5) |
C19—C6B—C7—C8 | 74.0 (3) | C18—C6A—C14A—C14 | 101.0 (3) |
C12B—C6B—C7—C8 | −45.5 (3) | C6—C6A—C14A—C14 | −143.0 (3) |
C6A—C6B—C7—C8 | −165.1 (2) | C6B—C6A—C14A—C14 | −20.6 (4) |
C6B—C7—C8—C8A | 57.2 (3) | C18—C6A—C14A—C14B | −72.7 (3) |
C7—C8—C8A—C12A | −64.4 (3) | C6—C6A—C14A—C14B | 43.2 (4) |
C7—C8—C8A—C9 | 162.6 (2) | C6B—C6A—C14A—C14B | 165.7 (2) |
C8—C8A—C9—C10 | 175.7 (3) | C2—C1—C14B—C14A | −175.9 (3) |
C12A—C8A—C9—C10 | 45.4 (4) | C2—C1—C14B—C4A | 57.0 (4) |
C8—C8A—C9—C20 | −64.7 (4) | C14—C14A—C14B—C1 | 5.9 (4) |
C12A—C8A—C9—C20 | 165.0 (3) | C6A—C14A—C14B—C1 | 179.6 (3) |
C8—C8A—C9—C21 | 54.7 (3) | C14—C14A—C14B—C4A | 133.0 (3) |
C12A—C8A—C9—C21 | −75.7 (3) | C6A—C14A—C14B—C4A | −53.3 (4) |
C20—C9—C10—O1 | 24.1 (4) | C5—C4A—C14B—C1 | −172.1 (3) |
C21—C9—C10—O1 | −91.3 (3) | C17—C4A—C14B—C1 | 66.0 (3) |
C8A—C9—C10—O1 | 143.3 (3) | C4—C4A—C14B—C1 | −56.0 (4) |
C20—C9—C10—C11 | −158.0 (3) | C5—C4A—C14B—C14A | 59.3 (4) |
C21—C9—C10—C11 | 86.5 (3) | C17—C4A—C14B—C14A | −62.5 (3) |
C8A—C9—C10—C11 | −38.9 (4) | C4—C4A—C14B—C14A | 175.4 (3) |
O1—C10—C11—C12 | −138.8 (3) | C16—C2—C15—O3 | 129.6 (4) |
C9—C10—C11—C12 | 43.3 (4) | C1—C2—C15—O3 | 6.8 (5) |
C10—C11—C12—C12A | −52.6 (4) | C3—C2—C15—O3 | −110.8 (4) |
C11—C12—C12A—C22 | −66.4 (3) | C16—C2—C15—O4 | −52.3 (3) |
C11—C12—C12A—C8A | 56.8 (3) | C1—C2—C15—O4 | −175.0 (3) |
C11—C12—C12A—C12B | 170.8 (2) | C3—C2—C15—O4 | 67.3 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O1i | 0.84 | 1.95 | 2.766 (3) | 163 |
C7—H7A···O2ii | 0.99 | 2.66 | 3.579 (4) | 155 |
C17—H17C···O3iii | 0.98 | 2.64 | 3.575 (4) | 159 |
C20—H20A···O4iv | 0.98 | 2.46 | 3.304 (4) | 144 |
C21—H21B···O4v | 0.98 | 2.69 | 3.225 (4) | 115 |
Symmetry codes: (i) x, y+1, z+1; (ii) x, y−1, z; (iii) x−1, y−1, z; (iv) x, y−1, z−1; (v) x−1, y−1, z−1. |