The title compound, C42H36O4, belongs to the class of calix[4]arenes. It assumes a cone conformation. The hydroxy groups form intramolecular hydrogen bonds to the ether O atoms.
Supporting information
CCDC reference: 248808
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.003 Å
- R factor = 0.060
- wR factor = 0.134
- Data-to-parameter ratio = 17.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.64
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 64.00 A 3
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 1990).
25,27-Bis(benzyloxy)-26,28-dihydroxycalix[4]arene
top
Crystal data top
C42H36O4 | Z = 2 |
Mr = 604.71 | F(000) = 640 |
Triclinic, P1 | Dx = 1.253 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.3942 (8) Å | Cell parameters from 503 reflections |
b = 12.501 (1) Å | θ = 1–25° |
c = 14.348 (1) Å | µ = 0.08 mm−1 |
α = 74.028 (4)° | T = 173 K |
β = 73.954 (4)° | Block, yellow |
γ = 65.501 (5)° | 0.43 × 0.28 × 0.22 mm |
V = 1602.7 (2) Å3 | |
Data collection top
Siemens CCD three-circle diffractometer | 4900 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.042 |
Graphite monochromator | θmax = 29.0°, θmin = 1.8° |
ω scans | h = −13→12 |
30084 measured reflections | k = −16→16 |
7409 independent reflections | l = −19→18 |
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)] = 0.060 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.134 | w = 1/[σ2(Fo2) + (0.0448P)2 + 0.7201P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
7409 reflections | Δρmax = 0.47 e Å−3 |
424 parameters | Δρmin = −0.18 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: 0.0109 (13) |
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 | −0.0740 (2) | 0.3542 (2) | 0.43585 (15) | 0.0411 (5) | |
H1A | −0.0789 | 0.4327 | 0.3936 | 0.049* | |
H1B | −0.1737 | 0.3589 | 0.4660 | 0.049* | |
C2 | 0.2735 (2) | 0.19922 (18) | 0.13425 (13) | 0.0340 (5) | |
H2A | 0.2620 | 0.2846 | 0.1141 | 0.041* | |
H2B | 0.2553 | 0.1756 | 0.0801 | 0.041* | |
C3 | 0.7125 (2) | 0.13576 (19) | 0.26519 (14) | 0.0371 (5) | |
H3A | 0.8160 | 0.0847 | 0.2557 | 0.045* | |
H3B | 0.7043 | 0.2192 | 0.2350 | 0.045* | |
C4 | 0.3597 (2) | 0.33153 (19) | 0.54873 (15) | 0.0414 (5) | |
H4A | 0.3787 | 0.3427 | 0.6086 | 0.050* | |
H4B | 0.3566 | 0.4039 | 0.4977 | 0.050* | |
C11 | −0.0048 (2) | 0.25878 (18) | 0.37202 (14) | 0.0356 (5) | |
C12 | 0.0845 (2) | 0.27509 (17) | 0.28112 (13) | 0.0318 (4) | |
C13 | 0.1635 (2) | 0.18415 (17) | 0.22636 (13) | 0.0317 (4) | |
C14 | 0.1408 (2) | 0.07655 (18) | 0.26185 (15) | 0.0390 (5) | |
H14 | 0.1911 | 0.0133 | 0.2256 | 0.047* | |
C15 | 0.0465 (2) | 0.0603 (2) | 0.34873 (16) | 0.0433 (5) | |
H15 | 0.0298 | −0.0126 | 0.3704 | 0.052* | |
C16 | −0.0236 (2) | 0.1496 (2) | 0.40413 (15) | 0.0416 (5) | |
H16 | −0.0855 | 0.1364 | 0.4650 | 0.050* | |
C21 | 0.4264 (2) | 0.12483 (17) | 0.14967 (13) | 0.0316 (4) | |
C22 | 0.4965 (2) | 0.16575 (16) | 0.19471 (13) | 0.0301 (4) | |
O22 | 0.42107 (16) | 0.27631 (12) | 0.21816 (11) | 0.0405 (4) | |
H22 | 0.459 (3) | 0.295 (2) | 0.2543 (18) | 0.055 (7)* | |
C23 | 0.6362 (2) | 0.09629 (17) | 0.21204 (13) | 0.0319 (4) | |
C24 | 0.7055 (2) | −0.01243 (18) | 0.17941 (14) | 0.0384 (5) | |
H24 | 0.8017 | −0.0594 | 0.1883 | 0.046* | |
C25 | 0.6385 (2) | −0.05380 (19) | 0.13454 (15) | 0.0430 (5) | |
H25 | 0.6875 | −0.1286 | 0.1134 | 0.052* | |
C26 | 0.4990 (2) | 0.01478 (18) | 0.12064 (13) | 0.0373 (5) | |
H26 | 0.4520 | −0.0142 | 0.0906 | 0.045* | |
C31 | 0.6519 (2) | 0.12868 (18) | 0.37505 (14) | 0.0337 (4) | |
C32 | 0.5506 (2) | 0.22896 (17) | 0.41313 (14) | 0.0328 (4) | |
C33 | 0.4828 (2) | 0.22396 (18) | 0.51196 (14) | 0.0358 (5) | |
C34 | 0.5285 (2) | 0.11428 (19) | 0.57505 (15) | 0.0399 (5) | |
H34 | 0.4867 | 0.1081 | 0.6432 | 0.048* | |
C35 | 0.6337 (2) | 0.0142 (2) | 0.54035 (15) | 0.0412 (5) | |
H35 | 0.6652 | −0.0593 | 0.5849 | 0.049* | |
C36 | 0.6931 (2) | 0.02077 (18) | 0.44092 (15) | 0.0369 (5) | |
H36 | 0.7627 | −0.0490 | 0.4173 | 0.044* | |
C41 | 0.2145 (2) | 0.31945 (18) | 0.57272 (14) | 0.0362 (5) | |
C42 | 0.1400 (2) | 0.34291 (17) | 0.49699 (14) | 0.0355 (5) | |
O42 | 0.20623 (16) | 0.37936 (14) | 0.40453 (10) | 0.0423 (4) | |
H42 | 0.156 (3) | 0.394 (2) | 0.3590 (19) | 0.060 (8)* | |
C43 | 0.0072 (2) | 0.33007 (18) | 0.51708 (14) | 0.0371 (5) | |
C44 | −0.0505 (2) | 0.2945 (2) | 0.61517 (15) | 0.0450 (5) | |
H44 | −0.1400 | 0.2843 | 0.6301 | 0.054* | |
C45 | 0.0195 (2) | 0.2738 (2) | 0.69095 (15) | 0.0477 (6) | |
H45 | −0.0223 | 0.2511 | 0.7574 | 0.057* | |
C46 | 0.1509 (2) | 0.28641 (19) | 0.66921 (14) | 0.0429 (5) | |
H46 | 0.1990 | 0.2722 | 0.7214 | 0.052* | |
O51 | 0.09980 (14) | 0.38603 (11) | 0.24539 (9) | 0.0338 (3) | |
C51 | 0.0037 (2) | 0.46524 (18) | 0.17883 (14) | 0.0365 (5) | |
H51A | −0.0936 | 0.5021 | 0.2170 | 0.044* | |
H51B | −0.0036 | 0.4193 | 0.1354 | 0.044* | |
C52 | 0.0589 (2) | 0.56131 (17) | 0.11717 (13) | 0.0327 (4) | |
C53 | 0.1969 (2) | 0.55341 (19) | 0.11102 (16) | 0.0425 (5) | |
H53 | 0.2603 | 0.4858 | 0.1471 | 0.051* | |
C54 | 0.2438 (3) | 0.6434 (2) | 0.05260 (18) | 0.0520 (6) | |
H54 | 0.3396 | 0.6369 | 0.0483 | 0.062* | |
C55 | 0.1521 (3) | 0.7429 (2) | 0.00040 (17) | 0.0541 (6) | |
H55 | 0.1842 | 0.8049 | −0.0391 | 0.065* | |
C56 | 0.0141 (3) | 0.7513 (2) | 0.00599 (17) | 0.0559 (7) | |
H56 | −0.0494 | 0.8193 | −0.0298 | 0.067* | |
C57 | −0.0322 (3) | 0.6609 (2) | 0.06365 (15) | 0.0455 (5) | |
H57 | −0.1274 | 0.6668 | 0.0667 | 0.055* | |
O61 | 0.51311 (14) | 0.33893 (11) | 0.34770 (10) | 0.0349 (3) | |
C61 | 0.6035 (2) | 0.40398 (19) | 0.34114 (16) | 0.0416 (5) | |
H61A | 0.7061 | 0.3532 | 0.3237 | 0.050* | |
H61B | 0.5884 | 0.4261 | 0.4056 | 0.050* | |
C62 | 0.5656 (2) | 0.51440 (18) | 0.26366 (15) | 0.0369 (5) | |
C63 | 0.4652 (3) | 0.6221 (2) | 0.28798 (17) | 0.0476 (6) | |
H63 | 0.4183 | 0.6261 | 0.3546 | 0.057* | |
C64 | 0.4326 (3) | 0.7239 (2) | 0.2161 (2) | 0.0594 (7) | |
H64 | 0.3640 | 0.7975 | 0.2336 | 0.071* | |
C65 | 0.4987 (3) | 0.7188 (2) | 0.1198 (2) | 0.0608 (7) | |
H65 | 0.4766 | 0.7892 | 0.0707 | 0.073* | |
C66 | 0.5964 (3) | 0.6130 (2) | 0.09386 (19) | 0.0590 (7) | |
H66 | 0.6408 | 0.6095 | 0.0268 | 0.071* | |
C67 | 0.6304 (3) | 0.5115 (2) | 0.16519 (17) | 0.0504 (6) | |
H67 | 0.6992 | 0.4384 | 0.1468 | 0.061* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0268 (11) | 0.0498 (13) | 0.0392 (11) | −0.0085 (10) | −0.0064 (9) | −0.0050 (10) |
C2 | 0.0408 (12) | 0.0347 (11) | 0.0302 (9) | −0.0146 (9) | −0.0140 (8) | −0.0029 (8) |
C3 | 0.0270 (11) | 0.0389 (12) | 0.0429 (11) | −0.0113 (9) | −0.0065 (8) | −0.0048 (9) |
C4 | 0.0492 (14) | 0.0416 (13) | 0.0396 (11) | −0.0148 (11) | −0.0149 (10) | −0.0131 (9) |
C11 | 0.0266 (11) | 0.0412 (12) | 0.0356 (10) | −0.0093 (9) | −0.0124 (8) | 0.0000 (9) |
C12 | 0.0311 (11) | 0.0313 (11) | 0.0344 (10) | −0.0121 (9) | −0.0159 (8) | 0.0027 (8) |
C13 | 0.0328 (11) | 0.0320 (11) | 0.0325 (10) | −0.0116 (9) | −0.0179 (8) | 0.0022 (8) |
C14 | 0.0412 (13) | 0.0331 (11) | 0.0454 (12) | −0.0135 (10) | −0.0188 (10) | −0.0007 (9) |
C15 | 0.0430 (13) | 0.0376 (12) | 0.0534 (13) | −0.0212 (11) | −0.0218 (11) | 0.0086 (10) |
C16 | 0.0336 (12) | 0.0502 (14) | 0.0387 (11) | −0.0192 (11) | −0.0129 (9) | 0.0075 (10) |
C21 | 0.0367 (11) | 0.0327 (11) | 0.0243 (9) | −0.0134 (9) | −0.0068 (8) | −0.0015 (8) |
C22 | 0.0322 (11) | 0.0281 (10) | 0.0275 (9) | −0.0104 (9) | −0.0046 (8) | −0.0032 (8) |
O22 | 0.0391 (9) | 0.0315 (8) | 0.0543 (9) | −0.0042 (7) | −0.0220 (7) | −0.0138 (7) |
C23 | 0.0302 (11) | 0.0319 (11) | 0.0300 (9) | −0.0122 (9) | −0.0039 (8) | −0.0006 (8) |
C24 | 0.0307 (11) | 0.0356 (12) | 0.0388 (11) | −0.0062 (9) | −0.0038 (9) | −0.0032 (9) |
C25 | 0.0472 (14) | 0.0345 (12) | 0.0409 (11) | −0.0082 (10) | −0.0025 (10) | −0.0137 (9) |
C26 | 0.0481 (13) | 0.0370 (12) | 0.0284 (10) | −0.0169 (10) | −0.0063 (9) | −0.0073 (8) |
C31 | 0.0257 (11) | 0.0403 (12) | 0.0411 (11) | −0.0162 (9) | −0.0118 (8) | −0.0045 (9) |
C32 | 0.0313 (11) | 0.0327 (11) | 0.0414 (11) | −0.0143 (9) | −0.0165 (9) | −0.0035 (8) |
C33 | 0.0358 (12) | 0.0394 (12) | 0.0411 (11) | −0.0161 (10) | −0.0154 (9) | −0.0087 (9) |
C34 | 0.0392 (12) | 0.0488 (13) | 0.0368 (11) | −0.0188 (11) | −0.0138 (9) | −0.0044 (9) |
C35 | 0.0382 (12) | 0.0421 (13) | 0.0455 (12) | −0.0161 (10) | −0.0196 (10) | 0.0024 (10) |
C36 | 0.0299 (11) | 0.0366 (12) | 0.0470 (12) | −0.0120 (9) | −0.0138 (9) | −0.0056 (9) |
C41 | 0.0378 (12) | 0.0325 (11) | 0.0361 (10) | −0.0060 (9) | −0.0075 (9) | −0.0131 (8) |
C42 | 0.0369 (12) | 0.0324 (11) | 0.0315 (10) | −0.0062 (9) | −0.0055 (8) | −0.0082 (8) |
O42 | 0.0421 (9) | 0.0562 (10) | 0.0320 (8) | −0.0222 (8) | −0.0099 (7) | −0.0034 (7) |
C43 | 0.0296 (11) | 0.0355 (12) | 0.0377 (11) | −0.0025 (9) | −0.0072 (8) | −0.0081 (9) |
C44 | 0.0336 (12) | 0.0483 (14) | 0.0405 (12) | −0.0062 (10) | −0.0014 (9) | −0.0085 (10) |
C45 | 0.0429 (14) | 0.0498 (14) | 0.0336 (11) | −0.0053 (11) | −0.0004 (10) | −0.0072 (10) |
C46 | 0.0477 (14) | 0.0407 (12) | 0.0327 (11) | −0.0033 (10) | −0.0108 (9) | −0.0120 (9) |
O51 | 0.0367 (8) | 0.0300 (7) | 0.0351 (7) | −0.0117 (6) | −0.0158 (6) | 0.0017 (6) |
C51 | 0.0346 (12) | 0.0341 (11) | 0.0388 (11) | −0.0097 (9) | −0.0169 (9) | 0.0016 (8) |
C52 | 0.0346 (11) | 0.0319 (11) | 0.0307 (10) | −0.0094 (9) | −0.0081 (8) | −0.0064 (8) |
C53 | 0.0403 (13) | 0.0362 (12) | 0.0479 (12) | −0.0120 (10) | −0.0129 (10) | −0.0014 (9) |
C54 | 0.0425 (14) | 0.0548 (15) | 0.0619 (15) | −0.0244 (12) | −0.0095 (11) | −0.0055 (12) |
C55 | 0.0675 (18) | 0.0533 (15) | 0.0443 (13) | −0.0348 (14) | −0.0087 (12) | 0.0055 (11) |
C56 | 0.0619 (17) | 0.0521 (15) | 0.0525 (14) | −0.0252 (13) | −0.0263 (12) | 0.0147 (11) |
C57 | 0.0453 (13) | 0.0462 (13) | 0.0442 (12) | −0.0188 (11) | −0.0193 (10) | 0.0071 (10) |
O61 | 0.0361 (8) | 0.0322 (8) | 0.0439 (8) | −0.0175 (6) | −0.0159 (6) | −0.0023 (6) |
C61 | 0.0376 (12) | 0.0403 (12) | 0.0573 (13) | −0.0203 (10) | −0.0184 (10) | −0.0056 (10) |
C62 | 0.0321 (11) | 0.0358 (12) | 0.0529 (12) | −0.0198 (10) | −0.0124 (9) | −0.0071 (9) |
C63 | 0.0474 (14) | 0.0468 (14) | 0.0504 (13) | −0.0173 (12) | −0.0091 (11) | −0.0118 (11) |
C64 | 0.0668 (18) | 0.0356 (13) | 0.0721 (17) | −0.0104 (12) | −0.0226 (14) | −0.0079 (12) |
C65 | 0.087 (2) | 0.0449 (15) | 0.0626 (16) | −0.0399 (15) | −0.0238 (15) | 0.0064 (12) |
C66 | 0.0727 (18) | 0.0585 (17) | 0.0524 (14) | −0.0413 (15) | 0.0014 (13) | −0.0062 (12) |
C67 | 0.0468 (14) | 0.0465 (14) | 0.0600 (15) | −0.0223 (12) | 0.0002 (11) | −0.0146 (11) |
Geometric parameters (Å, º) top
C1—C43 | 1.517 (3) | C35—C36 | 1.383 (3) |
C1—C11 | 1.518 (3) | C35—H35 | 0.9500 |
C1—H1A | 0.9900 | C36—H36 | 0.9500 |
C1—H1B | 0.9900 | C41—C46 | 1.389 (3) |
C2—C13 | 1.515 (3) | C41—C42 | 1.402 (3) |
C2—C21 | 1.515 (3) | C42—O42 | 1.365 (2) |
C2—H2A | 0.9900 | C42—C43 | 1.397 (3) |
C2—H2B | 0.9900 | O42—H42 | 0.88 (3) |
C3—C31 | 1.520 (3) | C43—C44 | 1.396 (3) |
C3—C23 | 1.523 (3) | C44—C45 | 1.380 (3) |
C3—H3A | 0.9900 | C44—H44 | 0.9500 |
C3—H3B | 0.9900 | C45—C46 | 1.379 (3) |
C4—C41 | 1.515 (3) | C45—H45 | 0.9500 |
C4—C33 | 1.521 (3) | C46—H46 | 0.9500 |
C4—H4A | 0.9900 | O51—C51 | 1.441 (2) |
C4—H4B | 0.9900 | C51—C52 | 1.503 (3) |
C11—C16 | 1.393 (3) | C51—H51A | 0.9900 |
C11—C12 | 1.395 (3) | C51—H51B | 0.9900 |
C12—C13 | 1.395 (3) | C52—C53 | 1.376 (3) |
C12—O51 | 1.399 (2) | C52—C57 | 1.391 (3) |
C13—C14 | 1.395 (3) | C53—C54 | 1.385 (3) |
C14—C15 | 1.381 (3) | C53—H53 | 0.9500 |
C14—H14 | 0.9500 | C54—C55 | 1.384 (3) |
C15—C16 | 1.379 (3) | C54—H54 | 0.9500 |
C15—H15 | 0.9500 | C55—C56 | 1.374 (3) |
C16—H16 | 0.9500 | C55—H55 | 0.9500 |
C21—C26 | 1.384 (3) | C56—C57 | 1.382 (3) |
C21—C22 | 1.401 (3) | C56—H56 | 0.9500 |
C22—O22 | 1.360 (2) | C57—H57 | 0.9500 |
C22—C23 | 1.400 (3) | O61—C61 | 1.448 (2) |
O22—H22 | 0.86 (3) | C61—C62 | 1.498 (3) |
C23—C24 | 1.392 (3) | C61—H61A | 0.9900 |
C24—C25 | 1.378 (3) | C61—H61B | 0.9900 |
C24—H24 | 0.9500 | C62—C63 | 1.384 (3) |
C25—C26 | 1.383 (3) | C62—C67 | 1.390 (3) |
C25—H25 | 0.9500 | C63—C64 | 1.383 (3) |
C26—H26 | 0.9500 | C63—H63 | 0.9500 |
C31—C36 | 1.393 (3) | C64—C65 | 1.369 (4) |
C31—C32 | 1.394 (3) | C64—H64 | 0.9500 |
C32—C33 | 1.395 (3) | C65—C66 | 1.366 (4) |
C32—O61 | 1.404 (2) | C65—H65 | 0.9500 |
C33—C34 | 1.393 (3) | C66—C67 | 1.377 (3) |
C34—C35 | 1.384 (3) | C66—H66 | 0.9500 |
C34—H34 | 0.9500 | C67—H67 | 0.9500 |
| | | |
C43—C1—C11 | 112.90 (16) | C36—C35—H35 | 119.9 |
C43—C1—H1A | 109.0 | C34—C35—H35 | 119.9 |
C11—C1—H1A | 109.0 | C35—C36—C31 | 120.7 (2) |
C43—C1—H1B | 109.0 | C35—C36—H36 | 119.7 |
C11—C1—H1B | 109.0 | C31—C36—H36 | 119.7 |
H1A—C1—H1B | 107.8 | C46—C41—C42 | 118.3 (2) |
C13—C2—C21 | 112.32 (15) | C46—C41—C4 | 121.50 (19) |
C13—C2—H2A | 109.1 | C42—C41—C4 | 120.17 (18) |
C21—C2—H2A | 109.1 | O42—C42—C43 | 123.63 (18) |
C13—C2—H2B | 109.1 | O42—C42—C41 | 115.15 (18) |
C21—C2—H2B | 109.1 | C43—C42—C41 | 121.22 (18) |
H2A—C2—H2B | 107.9 | C42—O42—H42 | 112.5 (16) |
C31—C3—C23 | 113.15 (16) | C44—C43—C42 | 118.05 (19) |
C31—C3—H3A | 108.9 | C44—C43—C1 | 120.15 (19) |
C23—C3—H3A | 108.9 | C42—C43—C1 | 121.80 (18) |
C31—C3—H3B | 108.9 | C45—C44—C43 | 121.6 (2) |
C23—C3—H3B | 108.9 | C45—C44—H44 | 119.2 |
H3A—C3—H3B | 107.8 | C43—C44—H44 | 119.2 |
C41—C4—C33 | 113.33 (17) | C46—C45—C44 | 119.3 (2) |
C41—C4—H4A | 108.9 | C46—C45—H45 | 120.4 |
C33—C4—H4A | 108.9 | C44—C45—H45 | 120.4 |
C41—C4—H4B | 108.9 | C45—C46—C41 | 121.5 (2) |
C33—C4—H4B | 108.9 | C45—C46—H46 | 119.2 |
H4A—C4—H4B | 107.7 | C41—C46—H46 | 119.2 |
C16—C11—C12 | 117.53 (19) | C12—O51—C51 | 113.06 (14) |
C16—C11—C1 | 121.02 (18) | O51—C51—C52 | 109.83 (16) |
C12—C11—C1 | 121.41 (18) | O51—C51—H51A | 109.7 |
C13—C12—C11 | 122.80 (18) | C52—C51—H51A | 109.7 |
C13—C12—O51 | 118.67 (17) | O51—C51—H51B | 109.7 |
C11—C12—O51 | 118.48 (18) | C52—C51—H51B | 109.7 |
C12—C13—C14 | 117.12 (18) | H51A—C51—H51B | 108.2 |
C12—C13—C2 | 121.79 (17) | C53—C52—C57 | 118.91 (19) |
C14—C13—C2 | 121.05 (18) | C53—C52—C51 | 122.24 (18) |
C15—C14—C13 | 121.2 (2) | C57—C52—C51 | 118.84 (18) |
C15—C14—H14 | 119.4 | C52—C53—C54 | 120.4 (2) |
C13—C14—H14 | 119.4 | C52—C53—H53 | 119.8 |
C16—C15—C14 | 120.21 (19) | C54—C53—H53 | 119.8 |
C16—C15—H15 | 119.9 | C55—C54—C53 | 120.4 (2) |
C14—C15—H15 | 119.9 | C55—C54—H54 | 119.8 |
C15—C16—C11 | 120.9 (2) | C53—C54—H54 | 119.8 |
C15—C16—H16 | 119.6 | C56—C55—C54 | 119.6 (2) |
C11—C16—H16 | 119.6 | C56—C55—H55 | 120.2 |
C26—C21—C22 | 118.73 (18) | C54—C55—H55 | 120.2 |
C26—C21—C2 | 120.80 (18) | C55—C56—C57 | 120.0 (2) |
C22—C21—C2 | 120.47 (17) | C55—C56—H56 | 120.0 |
O22—C22—C23 | 123.31 (17) | C57—C56—H56 | 120.0 |
O22—C22—C21 | 115.67 (17) | C56—C57—C52 | 120.8 (2) |
C23—C22—C21 | 121.01 (18) | C56—C57—H57 | 119.6 |
C22—O22—H22 | 114.4 (16) | C52—C57—H57 | 119.6 |
C24—C23—C22 | 117.92 (18) | C32—O61—C61 | 112.10 (14) |
C24—C23—C3 | 119.88 (18) | O61—C61—C62 | 108.81 (16) |
C22—C23—C3 | 122.20 (17) | O61—C61—H61A | 109.9 |
C25—C24—C23 | 121.8 (2) | C62—C61—H61A | 109.9 |
C25—C24—H24 | 119.1 | O61—C61—H61B | 109.9 |
C23—C24—H24 | 119.1 | C62—C61—H61B | 109.9 |
C24—C25—C26 | 119.3 (2) | H61A—C61—H61B | 108.3 |
C24—C25—H25 | 120.4 | C63—C62—C67 | 118.1 (2) |
C26—C25—H25 | 120.4 | C63—C62—C61 | 121.0 (2) |
C25—C26—C21 | 121.20 (19) | C67—C62—C61 | 120.9 (2) |
C25—C26—H26 | 119.4 | C64—C63—C62 | 120.5 (2) |
C21—C26—H26 | 119.4 | C64—C63—H63 | 119.7 |
C36—C31—C32 | 117.66 (18) | C62—C63—H63 | 119.7 |
C36—C31—C3 | 121.00 (19) | C65—C64—C63 | 120.2 (2) |
C32—C31—C3 | 121.32 (18) | C65—C64—H64 | 119.9 |
C31—C32—C33 | 123.03 (18) | C63—C64—H64 | 119.9 |
C31—C32—O61 | 117.89 (17) | C66—C65—C64 | 120.3 (2) |
C33—C32—O61 | 119.06 (17) | C66—C65—H65 | 119.9 |
C34—C33—C32 | 117.01 (19) | C64—C65—H65 | 119.9 |
C34—C33—C4 | 121.17 (18) | C65—C66—C67 | 119.9 (2) |
C32—C33—C4 | 121.76 (18) | C65—C66—H66 | 120.1 |
C35—C34—C33 | 121.27 (19) | C67—C66—H66 | 120.1 |
C35—C34—H34 | 119.4 | C66—C67—C62 | 121.0 (2) |
C33—C34—H34 | 119.4 | C66—C67—H67 | 119.5 |
C36—C35—C34 | 120.17 (19) | C62—C67—H67 | 119.5 |
| | | |
C43—C1—C11—C16 | 78.9 (2) | C4—C33—C34—C35 | 175.46 (18) |
C43—C1—C11—C12 | −98.5 (2) | C33—C34—C35—C36 | −1.7 (3) |
C16—C11—C12—C13 | −5.5 (3) | C34—C35—C36—C31 | 2.3 (3) |
C1—C11—C12—C13 | 171.93 (17) | C32—C31—C36—C35 | 0.6 (3) |
C16—C11—C12—O51 | 177.18 (17) | C3—C31—C36—C35 | −177.70 (18) |
C1—C11—C12—O51 | −5.4 (3) | C33—C4—C41—C46 | 100.5 (2) |
C11—C12—C13—C14 | 5.5 (3) | C33—C4—C41—C42 | −80.2 (2) |
O51—C12—C13—C14 | −177.18 (16) | C46—C41—C42—O42 | 177.57 (18) |
C11—C12—C13—C2 | −172.33 (17) | C4—C41—C42—O42 | −1.8 (3) |
O51—C12—C13—C2 | 5.0 (3) | C46—C41—C42—C43 | −1.9 (3) |
C21—C2—C13—C12 | 108.9 (2) | C4—C41—C42—C43 | 178.71 (18) |
C21—C2—C13—C14 | −68.9 (2) | O42—C42—C43—C44 | −178.67 (19) |
C12—C13—C14—C15 | −1.5 (3) | C41—C42—C43—C44 | 0.8 (3) |
C2—C13—C14—C15 | 176.38 (17) | O42—C42—C43—C1 | 1.0 (3) |
C13—C14—C15—C16 | −2.3 (3) | C41—C42—C43—C1 | −179.53 (19) |
C14—C15—C16—C11 | 2.3 (3) | C11—C1—C43—C44 | −108.3 (2) |
C12—C11—C16—C15 | 1.5 (3) | C11—C1—C43—C42 | 72.0 (3) |
C1—C11—C16—C15 | −176.01 (18) | C42—C43—C44—C45 | 0.8 (3) |
C13—C2—C21—C26 | 97.7 (2) | C1—C43—C44—C45 | −178.9 (2) |
C13—C2—C21—C22 | −81.5 (2) | C43—C44—C45—C46 | −1.2 (3) |
C26—C21—C22—O22 | 177.74 (16) | C44—C45—C46—C41 | 0.0 (3) |
C2—C21—C22—O22 | −3.0 (2) | C42—C41—C46—C45 | 1.6 (3) |
C26—C21—C22—C23 | −1.2 (3) | C4—C41—C46—C45 | −179.1 (2) |
C2—C21—C22—C23 | 178.07 (16) | C13—C12—O51—C51 | 87.4 (2) |
O22—C22—C23—C24 | −176.23 (17) | C11—C12—O51—C51 | −95.22 (19) |
C21—C22—C23—C24 | 2.6 (3) | C12—O51—C51—C52 | −160.16 (16) |
O22—C22—C23—C3 | 4.1 (3) | O51—C51—C52—C53 | 14.4 (3) |
C21—C22—C23—C3 | −177.05 (16) | O51—C51—C52—C57 | −166.37 (18) |
C31—C3—C23—C24 | −107.6 (2) | C57—C52—C53—C54 | 0.2 (3) |
C31—C3—C23—C22 | 72.0 (2) | C51—C52—C53—C54 | 179.4 (2) |
C22—C23—C24—C25 | −2.3 (3) | C52—C53—C54—C55 | 0.6 (4) |
C3—C23—C24—C25 | 177.37 (18) | C53—C54—C55—C56 | −0.7 (4) |
C23—C24—C25—C26 | 0.6 (3) | C54—C55—C56—C57 | 0.1 (4) |
C24—C25—C26—C21 | 1.0 (3) | C55—C56—C57—C52 | 0.6 (4) |
C22—C21—C26—C25 | −0.6 (3) | C53—C52—C57—C56 | −0.7 (3) |
C2—C21—C26—C25 | −179.90 (18) | C51—C52—C57—C56 | −180.0 (2) |
C23—C3—C31—C36 | 81.4 (2) | C31—C32—O61—C61 | −90.5 (2) |
C23—C3—C31—C32 | −96.8 (2) | C33—C32—O61—C61 | 91.2 (2) |
C36—C31—C32—C33 | −4.3 (3) | C32—O61—C61—C62 | 175.00 (17) |
C3—C31—C32—C33 | 173.99 (18) | O61—C61—C62—C63 | 92.9 (2) |
C36—C31—C32—O61 | 177.46 (16) | O61—C61—C62—C67 | −87.1 (2) |
C3—C31—C32—O61 | −4.2 (3) | C67—C62—C63—C64 | −1.0 (3) |
C31—C32—C33—C34 | 4.9 (3) | C61—C62—C63—C64 | 179.0 (2) |
O61—C32—C33—C34 | −176.94 (16) | C62—C63—C64—C65 | 0.5 (4) |
C31—C32—C33—C4 | −172.34 (17) | C63—C64—C65—C66 | 0.6 (4) |
O61—C32—C33—C4 | 5.9 (3) | C64—C65—C66—C67 | −1.2 (4) |
C41—C4—C33—C34 | −70.2 (2) | C65—C66—C67—C62 | 0.7 (4) |
C41—C4—C33—C32 | 106.9 (2) | C63—C62—C67—C66 | 0.4 (3) |
C32—C33—C34—C35 | −1.8 (3) | C61—C62—C67—C66 | −179.7 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O22—H22···O61 | 0.86 (3) | 1.87 (3) | 2.7179 (19) | 170 (2) |
O42—H42···O51 | 0.88 (3) | 1.91 (3) | 2.768 (2) | 162 (2) |