The structure of the title compound, C40H44O8, differs from previously determined structures of triptyceno-crown ether molecules as its longer crown ether chain does not congest a triptycene cavity.
Supporting information
CCDC reference: 180782
Key indicators
- Single-crystal X-ray study
- T = 233 K
- Mean (C-C) = 0.004 Å
- R factor = 0.048
- wR factor = 0.134
- Data-to-parameter ratio = 12.4
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Data collection: CAD-4-PC (Enraf-Nonius, 1993); cell refinement: CAD-4-PC; data reduction: XCAD4 (Harms, 1995); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2001).
Crystal data top
C40H44O8 | F(000) = 1392 |
Mr = 652.8 | Dx = 1.255 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 9.3198 (17) Å | θ = 10.1–12.2° |
b = 23.416 (2) Å | µ = 0.09 mm−1 |
c = 15.838 (3) Å | T = 233 K |
β = 91.333 (9)° | Plate, colourless |
V = 3455.4 (10) Å3 | 0.63 × 0.50 × 0.04 mm |
Z = 4 | |
Data collection top
Enraf-Nonius CAD-4 diffractometer | Rint = 0.029 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 2.1° |
Graphite monochromator | h = 0→11 |
ω scans | k = −16→27 |
7830 measured reflections | l = −18→18 |
6061 independent reflections | 3 standard reflections every 120 min |
3227 reflections with I > 2σ(I) | intensity decay: 2% |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.134 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.061P)2] where P = (Fo2 + 2Fc2)/3 |
6061 reflections | (Δ/σ)max = 0.001 |
487 parameters | Δρmax = 0.27 e Å−3 |
51 restraints | Δρmin = −0.28 e Å−3 |
0 constraints | |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All e.s.d.'s are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR
and all goodnesses of fit S are based on F2,
conventional R-factors R are based on F, with F
set to zero for negative F2. The observed criterion of F2 >
σ(F2) is used only for calculating -R-factor-obs
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 | 0.37625 (17) | 0.33879 (7) | 0.93471 (10) | 0.0460 (6) | |
O2 | 0.35324 (16) | 0.44710 (7) | 1.02445 (11) | 0.0432 (6) | |
O3 | 0.09346 (17) | 0.47780 (7) | 1.11586 (11) | 0.0521 (6) | |
O4 | −0.15915 (17) | 0.46637 (7) | 1.22264 (11) | 0.0503 (7) | |
O5 | −0.27604 (19) | 0.36083 (8) | 1.21919 (12) | 0.0588 (7) | |
O6 | −0.2829 (5) | 0.20700 (18) | 1.2127 (3) | 0.0683 (18) | 0.670 |
O7 | −0.2302 (14) | 0.0953 (7) | 1.1290 (10) | 0.065 (3) | 0.670 |
O8 | −0.04470 (17) | 0.10844 (7) | 0.97597 (11) | 0.0491 (6) | |
C1 | 0.2581 (2) | 0.25965 (9) | 0.86861 (14) | 0.0338 (8) | |
C2 | 0.0917 (2) | 0.16957 (9) | 0.88582 (14) | 0.0335 (8) | |
C3 | 0.3200 (2) | 0.21455 (9) | 0.92888 (14) | 0.0342 (8) | |
C4 | 0.2311 (2) | 0.16699 (9) | 0.93923 (14) | 0.0336 (8) | |
C5 | 0.2738 (3) | 0.12337 (11) | 0.99269 (16) | 0.0475 (9) | |
C6 | 0.4060 (3) | 0.12654 (13) | 1.03509 (18) | 0.0619 (11) | |
C7 | 0.4944 (3) | 0.17296 (13) | 1.02375 (18) | 0.0608 (11) | |
C8 | 0.4521 (2) | 0.21679 (11) | 0.97091 (16) | 0.0463 (9) | |
C9 | 0.1084 (2) | 0.27397 (9) | 0.90228 (13) | 0.0329 (8) | |
C10 | 0.0208 (2) | 0.22618 (10) | 0.91074 (14) | 0.0338 (8) | |
C11 | −0.1184 (2) | 0.23286 (11) | 0.93884 (15) | 0.0431 (9) | |
C12 | −0.1665 (3) | 0.28674 (12) | 0.95888 (17) | 0.0538 (10) | |
C13 | −0.0801 (3) | 0.33350 (11) | 0.95136 (17) | 0.0523 (10) | |
C14 | 0.0582 (3) | 0.32737 (10) | 0.92256 (15) | 0.0415 (8) | |
C15 | 0.2276 (2) | 0.22756 (10) | 0.78553 (14) | 0.0350 (8) | |
C16 | 0.1410 (2) | 0.17933 (10) | 0.79466 (14) | 0.0349 (8) | |
C17 | 0.1071 (3) | 0.14583 (11) | 0.72545 (15) | 0.0432 (8) | |
C18 | 0.1578 (3) | 0.16074 (12) | 0.64672 (16) | 0.0520 (10) | |
C19 | 0.2403 (3) | 0.20888 (12) | 0.63757 (16) | 0.0537 (10) | |
C20 | 0.2763 (3) | 0.24264 (11) | 0.70678 (16) | 0.0450 (9) | |
C21 | 0.3529 (3) | 0.31110 (10) | 0.85650 (15) | 0.0436 (9) | |
C22 | 0.4724 (2) | 0.38521 (10) | 0.93055 (16) | 0.0438 (9) | |
C23 | 0.4787 (2) | 0.41374 (10) | 1.01457 (17) | 0.0440 (9) | |
C24 | 0.3470 (3) | 0.46971 (11) | 1.10691 (17) | 0.0476 (9) | |
C25 | 0.2223 (3) | 0.50943 (11) | 1.11353 (18) | 0.0529 (10) | |
C26 | −0.0295 (3) | 0.51328 (11) | 1.11440 (18) | 0.0516 (10) | |
C27 | −0.1588 (3) | 0.47855 (12) | 1.13442 (17) | 0.0527 (10) | |
C28 | −0.2952 (3) | 0.45759 (11) | 1.25329 (16) | 0.0438 (9) | |
C29 | −0.3558 (3) | 0.40339 (11) | 1.25328 (16) | 0.0456 (9) | |
C30 | −0.4905 (3) | 0.39617 (12) | 1.28762 (18) | 0.0565 (10) | |
C31 | −0.5631 (3) | 0.44256 (15) | 1.31848 (19) | 0.0678 (11) | |
C32 | −0.5047 (3) | 0.49599 (14) | 1.31690 (19) | 0.0702 (11) | |
C33 | −0.3686 (3) | 0.50313 (13) | 1.28521 (18) | 0.0590 (11) | |
C34 | −0.3401 (14) | 0.3036 (5) | 1.2278 (9) | 0.050 (3) | 0.670 |
C35 | −0.2262 (10) | 0.2626 (3) | 1.2034 (7) | 0.065 (3) | 0.670 |
C36 | −0.1791 (6) | 0.1658 (2) | 1.2317 (3) | 0.0711 (19) | 0.670 |
C37 | −0.1211 (7) | 0.1344 (3) | 1.1594 (5) | 0.060 (3) | 0.670 |
C38 | −0.1757 (4) | 0.05180 (12) | 1.0711 (2) | 0.0701 (13) | |
C39 | −0.1582 (3) | 0.06820 (11) | 0.98109 (18) | 0.0598 (10) | |
C40 | −0.0043 (3) | 0.11774 (10) | 0.89102 (15) | 0.0441 (9) | |
C34A | −0.302 (3) | 0.3040 (11) | 1.219 (2) | 0.067 (7) | 0.330 |
C35A | −0.1826 (19) | 0.2696 (5) | 1.1853 (12) | 0.049 (5) | 0.330 |
C36A | −0.1056 (11) | 0.1749 (5) | 1.1706 (8) | 0.074 (4) | 0.330 |
C37A | −0.150 (2) | 0.1140 (6) | 1.1858 (10) | 0.094 (7) | 0.330 |
O7A | −0.229 (2) | 0.0963 (13) | 1.1122 (19) | 0.041 (4) | 0.330 |
O6A | −0.2251 (9) | 0.2120 (4) | 1.1810 (6) | 0.062 (3) | 0.330 |
H12 | −0.26050 | 0.29140 | 0.97810 | 0.0650* | |
H11 | −0.17900 | 0.20100 | 0.94410 | 0.0520* | |
H17 | 0.04990 | 0.11310 | 0.73150 | 0.0520* | |
H18 | 0.13560 | 0.13780 | 0.59950 | 0.0620* | |
H19 | 0.27260 | 0.21900 | 0.58380 | 0.0640* | |
H20 | 0.33330 | 0.27540 | 0.70030 | 0.0540* | |
H21A | 0.44490 | 0.29910 | 0.83360 | 0.0520* | |
H13 | −0.11450 | 0.36990 | 0.96580 | 0.0630* | |
H14 | 0.11760 | 0.35950 | 0.91690 | 0.0500* | |
H5 | 0.21380 | 0.09160 | 1.00050 | 0.0570* | |
H6 | 0.43510 | 0.09690 | 1.07160 | 0.0740* | |
H7 | 0.58400 | 0.17470 | 1.05220 | 0.0730* | |
H8 | 0.51280 | 0.24830 | 0.96330 | 0.0560* | |
H24B | 0.33740 | 0.43850 | 1.14760 | 0.0570* | |
H25A | 0.23300 | 0.53250 | 1.16490 | 0.0640* | |
H25B | 0.21940 | 0.53530 | 1.06490 | 0.0640* | |
H26A | −0.04210 | 0.53070 | 1.05840 | 0.0620* | |
H26B | −0.01730 | 0.54400 | 1.15600 | 0.0620* | |
H27A | −0.24600 | 0.49960 | 1.11820 | 0.0630* | |
H27B | −0.15780 | 0.44280 | 1.10230 | 0.0630* | |
H30 | −0.53200 | 0.35960 | 1.28970 | 0.0680* | |
H31 | −0.65460 | 0.43740 | 1.34110 | 0.0810* | |
H32 | −0.55620 | 0.52750 | 1.33700 | 0.0840* | |
H33 | −0.32620 | 0.53960 | 1.28560 | 0.0710* | |
H34A | −0.42480 | 0.29970 | 1.19040 | 0.0600* | 0.670 |
H34B | −0.36880 | 0.29690 | 1.28610 | 0.0600* | 0.670 |
H35A | −0.19910 | 0.26900 | 1.14480 | 0.0780* | 0.670 |
H35B | −0.14080 | 0.26740 | 1.24000 | 0.0780* | 0.670 |
H36A | −0.22070 | 0.13800 | 1.27040 | 0.0850* | 0.670 |
H36B | −0.09910 | 0.18440 | 1.26190 | 0.0850* | 0.670 |
H37A | −0.09570 | 0.16110 | 1.11460 | 0.0720* | 0.670 |
H37B | −0.03470 | 0.11330 | 1.17700 | 0.0720* | 0.670 |
H38A | −0.08210 | 0.03890 | 1.09330 | 0.0500* | |
H38B | −0.24070 | 0.01890 | 1.07250 | 0.0840* | |
H39A | −0.13620 | 0.03430 | 0.94750 | 0.0720* | |
H39B | −0.24750 | 0.08500 | 0.95860 | 0.0720* | |
H40A | −0.09030 | 0.12350 | 0.85530 | 0.0530* | |
H40B | 0.04660 | 0.08410 | 0.87020 | 0.0530* | |
H21B | 0.30700 | 0.33750 | 0.81620 | 0.0520* | |
H22A | 0.43940 | 0.41230 | 0.88710 | 0.0530* | |
H22B | 0.56800 | 0.37160 | 0.91580 | 0.0530* | |
H23A | 0.48550 | 0.38490 | 1.05940 | 0.0530* | |
H23B | 0.56380 | 0.43820 | 1.01890 | 0.0530* | |
H24A | 0.43610 | 0.49030 | 1.12060 | 0.0570* | |
H34C | −0.38840 | 0.29650 | 1.18440 | 0.0800* | 0.330 |
H34D | −0.32000 | 0.29150 | 1.27640 | 0.0800* | 0.330 |
H35C | −0.15820 | 0.28320 | 1.12890 | 0.0590* | 0.330 |
H35D | −0.09750 | 0.27340 | 1.22230 | 0.0590* | 0.330 |
H36C | −0.02820 | 0.18550 | 1.21050 | 0.0880* | 0.330 |
H36D | −0.06970 | 0.17880 | 1.11320 | 0.0880* | 0.330 |
H37C | −0.06550 | 0.08970 | 1.19480 | 0.1130* | 0.330 |
H37D | −0.20990 | 0.11150 | 1.23580 | 0.1130* | 0.330 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0457 (10) | 0.0412 (10) | 0.0516 (11) | −0.0180 (8) | 0.0091 (8) | −0.0071 (8) |
O2 | 0.0334 (9) | 0.0426 (10) | 0.0537 (12) | 0.0032 (8) | 0.0006 (8) | −0.0028 (8) |
O3 | 0.0390 (10) | 0.0427 (10) | 0.0754 (13) | 0.0036 (9) | 0.0166 (9) | 0.0100 (9) |
O4 | 0.0347 (10) | 0.0620 (12) | 0.0546 (12) | 0.0006 (8) | 0.0094 (8) | 0.0143 (9) |
O5 | 0.0552 (12) | 0.0454 (11) | 0.0761 (14) | 0.0009 (10) | 0.0096 (10) | 0.0033 (10) |
O6 | 0.072 (3) | 0.045 (2) | 0.088 (4) | −0.002 (2) | 0.001 (2) | −0.011 (2) |
O7 | 0.077 (5) | 0.046 (4) | 0.073 (8) | −0.002 (3) | 0.029 (4) | −0.008 (4) |
O8 | 0.0511 (11) | 0.0478 (10) | 0.0491 (12) | −0.0176 (9) | 0.0137 (9) | 0.0043 (8) |
C1 | 0.0290 (12) | 0.0331 (13) | 0.0395 (15) | −0.0044 (10) | 0.0068 (10) | 0.0012 (11) |
C2 | 0.0329 (13) | 0.0327 (13) | 0.0351 (14) | −0.0036 (11) | 0.0022 (11) | 0.0008 (10) |
C3 | 0.0302 (13) | 0.0382 (14) | 0.0343 (14) | 0.0054 (11) | 0.0042 (10) | −0.0048 (11) |
C4 | 0.0328 (13) | 0.0331 (13) | 0.0352 (14) | 0.0040 (11) | 0.0060 (11) | 0.0025 (11) |
C5 | 0.0509 (16) | 0.0423 (16) | 0.0496 (17) | 0.0045 (13) | 0.0068 (14) | 0.0086 (13) |
C6 | 0.0581 (19) | 0.070 (2) | 0.0572 (19) | 0.0229 (17) | −0.0044 (15) | 0.0177 (15) |
C7 | 0.0410 (16) | 0.079 (2) | 0.062 (2) | 0.0127 (16) | −0.0087 (14) | 0.0020 (17) |
C8 | 0.0305 (14) | 0.0552 (17) | 0.0532 (17) | 0.0017 (12) | 0.0020 (12) | −0.0025 (14) |
C9 | 0.0322 (13) | 0.0344 (13) | 0.0319 (14) | 0.0008 (11) | −0.0007 (10) | 0.0027 (10) |
C10 | 0.0320 (13) | 0.0388 (14) | 0.0306 (13) | −0.0003 (11) | −0.0010 (10) | 0.0015 (10) |
C11 | 0.0306 (13) | 0.0484 (16) | 0.0503 (17) | −0.0025 (12) | 0.0012 (12) | 0.0023 (12) |
C12 | 0.0291 (14) | 0.0625 (19) | 0.070 (2) | 0.0100 (14) | 0.0073 (13) | 0.0026 (15) |
C13 | 0.0460 (16) | 0.0422 (16) | 0.069 (2) | 0.0131 (14) | 0.0066 (14) | 0.0014 (14) |
C14 | 0.0381 (14) | 0.0370 (14) | 0.0492 (16) | 0.0021 (12) | −0.0004 (12) | 0.0043 (12) |
C15 | 0.0330 (13) | 0.0362 (13) | 0.0360 (14) | 0.0024 (11) | 0.0035 (11) | 0.0020 (11) |
C16 | 0.0327 (13) | 0.0346 (14) | 0.0375 (15) | 0.0003 (11) | 0.0020 (11) | −0.0008 (11) |
C17 | 0.0453 (14) | 0.0424 (14) | 0.0418 (16) | −0.0057 (12) | 0.0018 (12) | −0.0070 (12) |
C18 | 0.0600 (17) | 0.0574 (18) | 0.0385 (16) | −0.0020 (15) | 0.0005 (13) | −0.0092 (13) |
C19 | 0.0653 (18) | 0.0600 (18) | 0.0364 (16) | 0.0005 (15) | 0.0114 (14) | 0.0022 (14) |
C20 | 0.0477 (15) | 0.0426 (15) | 0.0451 (16) | −0.0049 (12) | 0.0113 (13) | 0.0041 (13) |
C21 | 0.0415 (14) | 0.0433 (15) | 0.0462 (16) | −0.0061 (12) | 0.0064 (12) | −0.0019 (12) |
C22 | 0.0311 (13) | 0.0380 (14) | 0.0625 (18) | −0.0111 (11) | 0.0073 (12) | −0.0024 (13) |
C23 | 0.0270 (13) | 0.0413 (15) | 0.0638 (19) | −0.0043 (11) | 0.0004 (12) | −0.0011 (13) |
C24 | 0.0413 (15) | 0.0457 (16) | 0.0560 (18) | −0.0037 (12) | 0.0050 (13) | −0.0011 (13) |
C25 | 0.0450 (16) | 0.0463 (16) | 0.068 (2) | −0.0052 (14) | 0.0121 (14) | −0.0052 (14) |
C26 | 0.0469 (15) | 0.0458 (16) | 0.0629 (19) | 0.0092 (13) | 0.0167 (13) | 0.0135 (13) |
C27 | 0.0383 (15) | 0.0695 (19) | 0.0507 (18) | 0.0072 (14) | 0.0072 (13) | 0.0069 (14) |
C28 | 0.0333 (14) | 0.0506 (17) | 0.0478 (16) | −0.0027 (13) | 0.0082 (12) | 0.0042 (13) |
C29 | 0.0430 (15) | 0.0483 (16) | 0.0455 (16) | 0.0000 (14) | 0.0009 (13) | 0.0045 (13) |
C30 | 0.0518 (17) | 0.0584 (18) | 0.0596 (19) | −0.0187 (15) | 0.0109 (14) | 0.0075 (15) |
C31 | 0.0555 (19) | 0.085 (2) | 0.064 (2) | −0.0134 (18) | 0.0254 (16) | −0.0118 (18) |
C32 | 0.0555 (19) | 0.077 (2) | 0.079 (2) | −0.0050 (17) | 0.0233 (17) | −0.0232 (17) |
C33 | 0.0504 (17) | 0.0569 (19) | 0.070 (2) | −0.0066 (15) | 0.0095 (15) | −0.0105 (15) |
C34 | 0.040 (6) | 0.047 (3) | 0.064 (5) | −0.004 (3) | −0.004 (4) | −0.004 (3) |
C35 | 0.069 (6) | 0.062 (4) | 0.065 (6) | 0.002 (3) | 0.018 (3) | 0.004 (3) |
C36 | 0.097 (4) | 0.055 (3) | 0.061 (3) | 0.005 (3) | −0.007 (3) | 0.003 (3) |
C37 | 0.055 (3) | 0.056 (5) | 0.069 (5) | 0.009 (3) | 0.001 (3) | 0.001 (4) |
C38 | 0.082 (2) | 0.0376 (16) | 0.093 (3) | −0.0010 (16) | 0.0491 (19) | 0.0011 (16) |
C39 | 0.0637 (18) | 0.0431 (16) | 0.074 (2) | −0.0194 (14) | 0.0296 (16) | −0.0080 (15) |
C40 | 0.0484 (15) | 0.0408 (15) | 0.0435 (16) | −0.0078 (12) | 0.0092 (13) | 0.0011 (12) |
C34A | 0.032 (12) | 0.052 (8) | 0.117 (16) | −0.012 (7) | −0.002 (8) | 0.009 (8) |
C35A | 0.075 (11) | 0.036 (5) | 0.036 (8) | −0.007 (5) | −0.005 (7) | −0.009 (5) |
C36A | 0.087 (8) | 0.052 (6) | 0.080 (8) | 0.007 (5) | −0.038 (7) | −0.011 (6) |
C37A | 0.143 (15) | 0.057 (7) | 0.080 (12) | 0.003 (8) | −0.037 (10) | 0.005 (8) |
O7A | 0.031 (6) | 0.054 (7) | 0.039 (7) | −0.002 (5) | 0.016 (4) | −0.005 (5) |
O6A | 0.067 (6) | 0.045 (4) | 0.074 (7) | −0.013 (4) | 0.004 (4) | −0.010 (4) |
Geometric parameters (Å, º) top
O1—C21 | 1.411 (3) | C34A—C35A | 1.48 (3) |
O1—C22 | 1.411 (3) | C36—C37 | 1.474 (9) |
O2—C23 | 1.418 (3) | C36A—C37A | 1.506 (19) |
O2—C24 | 1.412 (3) | C38—C39 | 1.489 (4) |
O3—C25 | 1.412 (3) | C5—H5 | 0.94 |
O3—C26 | 1.415 (3) | C6—H6 | 0.94 |
O4—C27 | 1.426 (3) | C7—H7 | 0.94 |
O4—C28 | 1.384 (3) | C8—H8 | 0.94 |
O5—C29 | 1.362 (3) | C11—H11 | 0.94 |
O5—C34 | 1.475 (12) | C12—H12 | 0.94 |
O5—C34A | 1.35 (3) | C13—H13 | 0.94 |
O6—C35 | 1.414 (9) | C14—H14 | 0.94 |
O6—C36 | 1.394 (7) | C17—H17 | 0.94 |
O6A—C35A | 1.407 (15) | C18—H18 | 0.94 |
O6A—C36A | 1.425 (14) | C19—H19 | 0.94 |
O7—C37 | 1.443 (16) | C20—H20 | 0.94 |
O7—C38 | 1.469 (16) | C21—H21A | 0.98 |
O7A—C38 | 1.33 (3) | C21—H21B | 0.98 |
O7A—C37A | 1.43 (3) | C22—H22A | 0.98 |
O8—C39 | 1.420 (3) | C22—H22B | 0.98 |
O8—C40 | 1.422 (3) | C23—H23A | 0.98 |
C1—C3 | 1.528 (3) | C23—H23B | 0.98 |
C1—C9 | 1.542 (3) | C24—H24A | 0.98 |
C1—C15 | 1.536 (3) | C24—H24B | 0.98 |
C1—C21 | 1.509 (3) | C25—H25A | 0.98 |
C2—C10 | 1.537 (3) | C25—H25B | 0.98 |
C2—C16 | 1.542 (3) | C26—H26A | 0.98 |
C2—C4 | 1.535 (3) | C26—H26B | 0.98 |
C2—C40 | 1.511 (3) | C27—H27A | 0.98 |
C3—C8 | 1.387 (3) | C27—H27B | 0.98 |
C3—C4 | 1.400 (3) | C30—H30 | 0.94 |
C4—C5 | 1.379 (3) | C31—H31 | 0.94 |
C5—C6 | 1.391 (4) | C32—H32 | 0.94 |
C6—C7 | 1.378 (4) | C33—H33 | 0.94 |
C7—C8 | 1.376 (4) | C34—H34A | 0.98 |
C9—C10 | 1.394 (3) | C34—H34B | 0.98 |
C9—C14 | 1.376 (3) | C34A—H34D | 0.97 |
C10—C11 | 1.390 (3) | C34A—H34C | 0.98 |
C11—C12 | 1.378 (4) | C35—H35B | 0.98 |
C12—C13 | 1.366 (4) | C35—H35A | 0.98 |
C13—C14 | 1.385 (4) | C35A—H35C | 0.98 |
C15—C20 | 1.383 (3) | C35A—H35D | 0.98 |
C15—C16 | 1.398 (3) | C36—H36B | 0.98 |
C16—C17 | 1.379 (3) | C36—H36A | 0.98 |
C17—C18 | 1.388 (4) | C36A—H36D | 0.98 |
C18—C19 | 1.374 (4) | C36A—H36C | 0.98 |
C19—C20 | 1.386 (4) | C37—H37A | 0.98 |
C22—C23 | 1.489 (4) | C37—H37B | 0.98 |
C24—C25 | 1.494 (4) | C37A—H37C | 0.98 |
C26—C27 | 1.494 (4) | C37A—H37D | 0.98 |
C28—C29 | 1.389 (4) | C38—H38B | 0.98 |
C28—C33 | 1.370 (4) | C38—H38A | 0.98 |
C29—C30 | 1.390 (4) | C39—H39A | 0.98 |
C30—C31 | 1.376 (4) | C39—H39B | 0.98 |
C31—C32 | 1.365 (5) | C40—H40A | 0.98 |
C32—C33 | 1.385 (4) | C40—H40B | 0.98 |
C34—C35 | 1.489 (15) | | |
| | | |
C21—O1—C22 | 113.47 (18) | C20—C19—H19 | 120 |
C23—O2—C24 | 111.13 (19) | C15—C20—H20 | 120 |
C25—O3—C26 | 112.36 (19) | C19—C20—H20 | 120 |
C27—O4—C28 | 113.36 (19) | O1—C21—H21A | 110 |
C29—O5—C34 | 113.7 (5) | O1—C21—H21B | 110 |
C29—O5—C34A | 128.4 (12) | C1—C21—H21A | 110 |
C35—O6—C36 | 113.6 (5) | C1—C21—H21B | 110 |
C35A—O6A—C36A | 111.7 (10) | H21A—C21—H21B | 108 |
C37—O7—C38 | 113.4 (9) | O1—C22—H22A | 110 |
C37A—O7A—C38 | 115.8 (18) | O1—C22—H22B | 110 |
C39—O8—C40 | 111.68 (19) | C23—C22—H22A | 110 |
C3—C1—C9 | 105.41 (17) | C23—C22—H22B | 110 |
C9—C1—C15 | 104.58 (15) | H22A—C22—H22B | 108 |
C3—C1—C15 | 104.88 (17) | O2—C23—H23A | 110 |
C3—C1—C21 | 114.69 (17) | O2—C23—H23B | 110 |
C15—C1—C21 | 112.27 (18) | C22—C23—H23A | 110 |
C9—C1—C21 | 114.05 (18) | C22—C23—H23B | 110 |
C4—C2—C40 | 115.66 (18) | H23A—C23—H23B | 108 |
C10—C2—C16 | 104.59 (17) | O2—C24—H24A | 110 |
C10—C2—C40 | 114.84 (17) | O2—C24—H24B | 110 |
C16—C2—C40 | 111.08 (18) | C25—C24—H24A | 110 |
C4—C2—C10 | 104.83 (17) | C25—C24—H24B | 110 |
C4—C2—C16 | 104.77 (15) | H24A—C24—H24B | 108 |
C1—C3—C8 | 126.29 (19) | O3—C25—H25A | 110 |
C1—C3—C4 | 114.03 (17) | O3—C25—H25B | 110 |
C4—C3—C8 | 119.7 (2) | C24—C25—H25A | 110 |
C2—C4—C5 | 126.6 (2) | C24—C25—H25B | 110 |
C3—C4—C5 | 119.9 (2) | H25A—C25—H25B | 108 |
C2—C4—C3 | 113.57 (18) | O3—C26—H26A | 110 |
C4—C5—C6 | 119.8 (2) | O3—C26—H26B | 110 |
C5—C6—C7 | 120.3 (3) | C27—C26—H26A | 110 |
C6—C7—C8 | 120.3 (3) | C27—C26—H26B | 110 |
C3—C8—C7 | 120.1 (2) | H26A—C26—H26B | 108 |
C10—C9—C14 | 120.3 (2) | O4—C27—H27A | 110 |
C1—C9—C14 | 126.4 (2) | O4—C27—H27B | 110 |
C1—C9—C10 | 113.29 (18) | C26—C27—H27A | 110 |
C2—C10—C9 | 114.31 (17) | C26—C27—H27B | 110 |
C2—C10—C11 | 126.1 (2) | H27A—C27—H27B | 108 |
C9—C10—C11 | 119.6 (2) | C29—C30—H30 | 120 |
C10—C11—C12 | 119.2 (2) | C31—C30—H30 | 120 |
C11—C12—C13 | 121.2 (2) | C30—C31—H31 | 119 |
C12—C13—C14 | 120.1 (2) | C32—C31—H31 | 119 |
C9—C14—C13 | 119.7 (2) | C31—C32—H32 | 120 |
C1—C15—C16 | 113.73 (19) | C33—C32—H32 | 120 |
C1—C15—C20 | 126.1 (2) | C28—C33—H33 | 120 |
C16—C15—C20 | 120.1 (2) | C32—C33—H33 | 120 |
C2—C16—C15 | 113.70 (19) | O5—C34—H34A | 111 |
C15—C16—C17 | 120.0 (2) | O5—C34—H34B | 111 |
C2—C16—C17 | 126.3 (2) | C35—C34—H34A | 111 |
C16—C17—C18 | 119.6 (2) | C35—C34—H34B | 111 |
C17—C18—C19 | 120.3 (2) | H34A—C34—H34B | 109 |
C18—C19—C20 | 120.7 (2) | C35A—C34A—H34C | 108 |
C15—C20—C19 | 119.3 (2) | O5—C34A—H34C | 109 |
O1—C21—C1 | 109.53 (19) | O5—C34A—H34D | 109 |
O1—C22—C23 | 108.41 (19) | C35A—C34A—H34D | 109 |
O2—C23—C22 | 109.29 (18) | H34C—C34A—H34D | 108 |
O2—C24—C25 | 110.3 (2) | O6—C35—H35A | 110 |
O3—C25—C24 | 109.8 (2) | H35A—C35—H35B | 109 |
O3—C26—C27 | 109.5 (2) | O6—C35—H35B | 110 |
O4—C27—C26 | 109.7 (2) | C34—C35—H35A | 110 |
C29—C28—C33 | 120.3 (3) | C34—C35—H35B | 110 |
O4—C28—C29 | 120.8 (2) | O6A—C35A—H35D | 110 |
O4—C28—C33 | 118.9 (2) | C34A—C35A—H35C | 110 |
C28—C29—C30 | 118.8 (2) | C34A—C35A—H35D | 110 |
O5—C29—C30 | 124.9 (2) | O6A—C35A—H35C | 110 |
O5—C29—C28 | 116.3 (2) | H35C—C35A—H35D | 108 |
C29—C30—C31 | 119.9 (3) | O6—C36—H36B | 108 |
C30—C31—C32 | 121.2 (3) | C37—C36—H36A | 108 |
C31—C32—C33 | 119.1 (3) | O6—C36—H36A | 108 |
C28—C33—C32 | 120.6 (3) | H36A—C36—H36B | 107 |
O5—C34—C35 | 105.6 (9) | C37—C36—H36B | 108 |
O5—C34A—C35A | 114 (2) | O6A—C36A—H36D | 110 |
O6—C35—C34 | 107.2 (8) | C37A—C36A—H36C | 110 |
O6A—C35A—C34A | 109.0 (15) | H36C—C36A—H36D | 108 |
O6—C36—C37 | 116.3 (5) | C37A—C36A—H36D | 110 |
O6A—C36A—C37A | 109.9 (10) | O6A—C36A—H36C | 110 |
O7—C37—C36 | 107.9 (8) | H37A—C37—H37B | 109 |
O7A—C37A—C36A | 106.5 (16) | O7—C37—H37A | 110 |
O7—C38—C39 | 117.8 (7) | O7—C37—H37B | 110 |
O7A—C38—C39 | 108.5 (13) | C36—C37—H37A | 110 |
O8—C39—C38 | 108.9 (2) | C36—C37—H37B | 110 |
O8—C40—C2 | 110.16 (19) | O7A—C37A—H37C | 110 |
C4—C5—H5 | 120 | C36A—C37A—H37D | 110 |
C6—C5—H5 | 120 | O7A—C37A—H37D | 110 |
C5—C6—H6 | 120 | C36A—C37A—H37C | 111 |
C7—C6—H6 | 120 | H37C—C37A—H37D | 109 |
C6—C7—H7 | 120 | O7—C38—H38A | 108 |
C8—C7—H7 | 120 | O7A—C38—H38B | 111 |
C3—C8—H8 | 120 | O7A—C38—H38A | 114 |
C7—C8—H8 | 120 | C39—C38—H38A | 108 |
C10—C11—H11 | 120 | C39—C38—H38B | 108 |
C12—C11—H11 | 120 | O7—C38—H38B | 108 |
C11—C12—H12 | 119 | H38A—C38—H38B | 107 |
C13—C12—H12 | 119 | O8—C39—H39B | 110 |
C12—C13—H13 | 120 | C38—C39—H39A | 110 |
C14—C13—H13 | 120 | O8—C39—H39A | 110 |
C9—C14—H14 | 120 | H39A—C39—H39B | 108 |
C13—C14—H14 | 120 | C38—C39—H39B | 110 |
C16—C17—H17 | 120 | H40A—C40—H40B | 108 |
C18—C17—H17 | 120 | C2—C40—H40B | 110 |
C17—C18—H18 | 120 | O8—C40—H40A | 110 |
C19—C18—H18 | 120 | O8—C40—H40B | 110 |
C18—C19—H19 | 120 | C2—C40—H40A | 110 |
| | | |
C22—O1—C21—C1 | 175.73 (17) | C4—C2—C16—C15 | −55.8 (2) |
C21—O1—C22—C23 | 175.31 (18) | C40—C2—C16—C15 | 178.60 (19) |
C24—O2—C23—C22 | 173.31 (19) | C40—C2—C16—C17 | −1.2 (3) |
C23—O2—C24—C25 | 174.2 (2) | C10—C2—C16—C17 | −125.6 (2) |
C26—O3—C25—C24 | −174.6 (2) | C4—C2—C40—O8 | 58.9 (3) |
C25—O3—C26—C27 | −168.7 (2) | C1—C3—C4—C2 | 1.5 (3) |
C28—O4—C27—C26 | 153.3 (2) | C1—C3—C4—C5 | −179.4 (2) |
C27—O4—C28—C29 | 89.3 (3) | C4—C3—C8—C7 | −1.2 (4) |
C27—O4—C28—C33 | −91.9 (3) | C8—C3—C4—C2 | −177.5 (2) |
C34—O5—C29—C28 | 174.9 (6) | C8—C3—C4—C5 | 1.6 (3) |
C34—O5—C29—C30 | −4.8 (7) | C1—C3—C8—C7 | 179.9 (2) |
C29—O5—C34—C35 | −168.9 (7) | C2—C4—C5—C6 | 178.1 (2) |
C36—O6—C35—C34 | −151.2 (8) | C3—C4—C5—C6 | −0.9 (4) |
C35—O6—C36—C37 | −93.9 (7) | C4—C5—C6—C7 | −0.1 (4) |
C38—O7—C37—C36 | −165.9 (8) | C5—C6—C7—C8 | 0.5 (4) |
C37—O7—C38—C39 | −81.4 (11) | C6—C7—C8—C3 | 0.1 (4) |
C40—O8—C39—C38 | 168.9 (2) | C1—C9—C14—C13 | 179.3 (2) |
C39—O8—C40—C2 | 167.38 (19) | C1—C9—C10—C2 | 0.6 (3) |
C3—C1—C15—C16 | 54.3 (2) | C10—C9—C14—C13 | −0.1 (3) |
C21—C1—C9—C10 | 178.22 (19) | C14—C9—C10—C11 | 0.8 (3) |
C21—C1—C9—C14 | −1.2 (3) | C1—C9—C10—C11 | −178.7 (2) |
C9—C1—C3—C4 | 53.9 (2) | C14—C9—C10—C2 | −179.9 (2) |
C9—C1—C3—C8 | −127.1 (2) | C9—C10—C11—C12 | −0.8 (3) |
C15—C1—C3—C4 | −56.2 (2) | C2—C10—C11—C12 | 180.0 (2) |
C15—C1—C3—C8 | 122.8 (2) | C10—C11—C12—C13 | 0.2 (4) |
C21—C1—C3—C4 | −179.77 (19) | C11—C12—C13—C14 | 0.5 (4) |
C21—C1—C3—C8 | −0.8 (3) | C12—C13—C14—C9 | −0.5 (4) |
C3—C1—C9—C10 | −55.1 (2) | C1—C15—C16—C17 | −178.8 (2) |
C3—C1—C9—C14 | 125.5 (2) | C20—C15—C16—C2 | −178.1 (2) |
C15—C1—C9—C10 | 55.2 (2) | C20—C15—C16—C17 | 1.7 (3) |
C15—C1—C9—C14 | −124.2 (2) | C1—C15—C16—C2 | 1.4 (2) |
C21—C1—C15—C20 | −1.1 (3) | C1—C15—C20—C19 | 179.5 (2) |
C3—C1—C21—O1 | −60.7 (3) | C16—C15—C20—C19 | −1.1 (4) |
C9—C1—C21—O1 | 61.0 (2) | C2—C16—C17—C18 | 178.9 (2) |
C3—C1—C15—C20 | −126.2 (2) | C15—C16—C17—C18 | −0.9 (4) |
C9—C1—C15—C16 | −56.4 (2) | C16—C17—C18—C19 | −0.6 (4) |
C9—C1—C15—C20 | 123.1 (2) | C17—C18—C19—C20 | 1.2 (4) |
C21—C1—C15—C16 | 179.47 (19) | C18—C19—C20—C15 | −0.3 (4) |
C15—C1—C21—O1 | 179.71 (17) | O1—C22—C23—O2 | −76.4 (2) |
C4—C2—C10—C9 | 54.5 (2) | O2—C24—C25—O3 | 74.4 (3) |
C4—C2—C10—C11 | −126.2 (2) | O3—C26—C27—O4 | 75.3 (3) |
C40—C2—C4—C5 | −2.3 (3) | O4—C28—C33—C32 | −179.6 (2) |
C10—C2—C4—C3 | −55.7 (2) | C33—C28—C29—O5 | 179.1 (2) |
C10—C2—C4—C5 | 125.3 (2) | C33—C28—C29—C30 | −1.2 (4) |
C16—C2—C4—C3 | 54.1 (2) | O4—C28—C29—O5 | −2.1 (4) |
C16—C2—C4—C5 | −124.9 (2) | O4—C28—C29—C30 | 177.6 (2) |
C40—C2—C4—C3 | 176.76 (19) | C29—C28—C33—C32 | −0.8 (4) |
C10—C2—C40—O8 | −63.5 (3) | O5—C29—C30—C31 | −178.4 (3) |
C16—C2—C40—O8 | 178.11 (17) | C28—C29—C30—C31 | 2.0 (4) |
C4—C2—C16—C17 | 124.4 (2) | C29—C30—C31—C32 | −0.7 (4) |
C10—C2—C16—C15 | 54.2 (2) | C30—C31—C32—C33 | −1.4 (5) |
C16—C2—C10—C9 | −55.4 (2) | C31—C32—C33—C28 | 2.1 (4) |
C16—C2—C10—C11 | 123.8 (2) | O5—C34—C35—O6 | 178.7 (8) |
C40—C2—C10—C9 | −177.42 (19) | O6—C36—C37—O7 | −73.0 (9) |
C40—C2—C10—C11 | 1.8 (3) | O7—C38—C39—O8 | 68.5 (7) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O8 | 0.94 | 2.46 | 2.994 (3) | 116 |
C8—H8···O1 | 0.94 | 2.51 | 2.995 (3) | 113 |
C11—H11···O8 | 0.94 | 2.55 | 3.047 (3) | 114 |
C14—H14···O1 | 0.94 | 2.47 | 2.978 (3) | 114 |
C37—H37A···O8 | 0.98 | 2.57 | 3.068 (8) | 111 |