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The absolute configuration of the title compound, C38H44O8, and in particular of its chiral cyclo­phane moiety, was determined by reference to the internal standard, (1S)-camphanoate. Molecules are associated into columns parallel to the b axis by a series of C—H...O interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802022328/bt6213sup1.cif
Contains datablocks 3, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802022328/bt62133sup2.hkl
Contains datablock 3

CCDC reference: 202987

Key indicators

  • Single-crystal X-ray study
  • T = 178 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.037
  • wR factor = 0.095
  • Data-to-parameter ratio = 9.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Red Alert Alert Level A:
DIFF_012 Alert A _diffrn_reflns_av_R_equivalents is missing R factor for symmetry-equivalent intensities. The following tests will not be performed RINTA PLAT_728 Alert A D-H..A Calc 166.66, Rep 1667.00, Dev. 1500.34 Deg. C9 -H9A -O30 1.555 1.555 1.455 General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 4034 Count of symmetry unique reflns 3728 Completeness (_total/calc) 108.21% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 306 Fraction of Friedel pairs measured 0.082 Are heavy atom types Z>Si present no ALERT: MoKa measured Friedel data cannot be used to determine absolute structure in a light-atom study EXCEPT under VERY special conditions. It is preferred that Friedel data is merged in such cases.
2 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
0 Alert Level C = Please check

Computing details top

Data collection: P3 (Nicolet, 1987); cell refinement: P3; data reduction: XDISK (1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.

(S)-4,16-Dihydroxymethyl-[2.2]paracyclophane bis-(1S)-camphanoate top
Crystal data top
C38H44O8Z = 1
Mr = 628.73F(000) = 336
Triclinic, P1Dx = 1.292 Mg m3
a = 6.740 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.295 (3) ÅCell parameters from 49 reflections
c = 11.647 (3) Åθ = 10–11.5°
α = 67.18 (2)°µ = 0.09 mm1
β = 81.59 (2)°T = 178 K
γ = 85.49 (2)°Prism, colourless
V = 808.2 (4) Å30.70 × 0.35 × 0.20 mm
Data collection top
Nicolet R3
diffractometer
θmax = 27.5°, θmin = 3.1°
Radiation source: fine-focus sealed tubeh = 80
Graphite monochromatork = 1414
ωn scansl = 1514
4034 measured reflections3 standard reflections every 147 reflections
4034 independent reflections intensity decay: none
3519 reflections with I > 2σ(I)
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0482P)2 + 0.1873P]
where P = (Fo2 + 2Fc2)/3
4034 reflections(Δ/σ)max < 0.001
421 parametersΔρmax = 0.19 e Å3
453 restraintsΔρmin = 0.22 e Å3
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
xyzUiso*/Ueq
C10.5265 (5)0.9990 (3)0.3334 (3)0.0424 (7)
H1A0.62930.97290.27720.051*
H1B0.56101.08510.32700.051*
C20.3163 (4)1.0089 (2)0.2861 (2)0.0360 (6)
H2A0.27611.10060.24690.043*
H2B0.32860.97190.22080.043*
C30.1544 (4)0.9398 (2)0.3904 (2)0.0258 (5)
C40.0925 (3)0.8158 (2)0.4130 (2)0.0242 (4)
C50.0213 (3)0.7341 (2)0.5351 (2)0.0241 (4)
H50.01700.64970.55020.029*
C60.0056 (3)0.7745 (2)0.6352 (2)0.0287 (5)
C70.0185 (4)0.9056 (2)0.6046 (2)0.0302 (5)
H70.02440.94010.66690.036*
C80.0926 (4)0.9865 (2)0.4851 (2)0.0305 (5)
H80.10191.07560.46690.037*
C90.0097 (4)0.6810 (3)0.7692 (2)0.0367 (6)
H9A0.03460.59630.77710.044*
H9B0.08710.71130.82500.044*
C100.2261 (5)0.6637 (3)0.8150 (2)0.0388 (6)
H10A0.22060.69750.88210.047*
H10B0.26190.57100.85110.047*
C110.3881 (4)0.7324 (2)0.7091 (2)0.0298 (5)
C120.4381 (4)0.8573 (2)0.6881 (2)0.0339 (5)
H120.42240.88460.75650.041*
C130.5105 (4)0.9426 (2)0.5687 (3)0.0355 (6)
H130.54321.02730.55630.043*
C140.5352 (4)0.9045 (2)0.4677 (2)0.0318 (5)
C150.5296 (3)0.7732 (2)0.4950 (2)0.0280 (5)
H150.57650.74180.43090.034*
C160.4573 (3)0.6874 (2)0.6137 (2)0.0260 (5)
C170.1057 (4)0.7661 (2)0.3094 (2)0.0287 (5)
H17A0.00410.70570.32720.034*
H17B0.09060.83850.22880.034*
O170.3001 (3)0.70012 (15)0.29985 (15)0.0292 (4)
C180.4348 (4)0.5498 (2)0.6300 (2)0.0312 (5)
H18A0.31000.51450.68570.037*
H18B0.42920.54420.54770.037*
O180.6117 (3)0.47748 (15)0.68636 (15)0.0308 (4)
C190.3429 (4)0.6714 (2)0.1981 (2)0.0280 (5)
O190.2371 (3)0.69805 (19)0.11642 (17)0.0426 (5)
C200.5391 (4)0.5977 (2)0.1960 (2)0.0251 (4)
O200.6523 (3)0.59661 (15)0.29415 (15)0.0295 (4)
C210.6824 (4)0.6478 (2)0.0727 (2)0.0324 (5)
H21A0.74730.72760.06230.039*
H21B0.61190.66380.00090.039*
C220.8361 (4)0.5346 (2)0.0924 (2)0.0326 (5)
H22A0.97220.56160.09280.039*
H22B0.84050.50010.02580.039*
C230.7561 (3)0.4330 (2)0.2231 (2)0.0255 (4)
C240.7848 (4)0.4952 (2)0.3137 (2)0.0281 (5)
O240.9019 (3)0.47038 (18)0.38927 (17)0.0361 (4)
C250.5244 (3)0.4519 (2)0.2238 (2)0.0244 (4)
C260.4405 (4)0.4232 (2)0.1227 (2)0.0331 (5)
H26A0.44420.33020.14430.040*
H26B0.52180.46540.04160.040*
H26C0.30160.45570.11740.040*
C270.4054 (4)0.3782 (2)0.3523 (2)0.0310 (5)
H27A0.26550.40920.35240.037*
H27B0.46420.39210.41800.037*
H27C0.41070.28620.36840.037*
C280.8493 (4)0.2998 (2)0.2557 (2)0.0334 (5)
H28A0.99430.30390.25440.040*
H28B0.82360.26520.19420.040*
H28C0.79040.24380.33970.040*
C290.6389 (4)0.3607 (2)0.6834 (2)0.0265 (5)
O290.5302 (3)0.31145 (16)0.64158 (16)0.0348 (4)
C300.8202 (4)0.2893 (2)0.7412 (2)0.0253 (4)
O300.9363 (3)0.36855 (15)0.77927 (17)0.0353 (4)
C310.9723 (4)0.2382 (3)0.6579 (2)0.0354 (6)
H31A1.05310.30820.59270.042*
H31B0.90470.19300.61720.042*
C321.1021 (4)0.1445 (2)0.7552 (2)0.0333 (5)
H32A1.24310.17210.73580.040*
H32B1.09870.05620.75730.040*
C331.0038 (4)0.1513 (2)0.8822 (2)0.0272 (5)
C341.0475 (4)0.2860 (2)0.8676 (2)0.0321 (5)
O341.1590 (3)0.32332 (19)0.9172 (2)0.0485 (5)
C350.7768 (3)0.1699 (2)0.8656 (2)0.0254 (4)
C360.6482 (4)0.2045 (3)0.9675 (2)0.0419 (6)
H36A0.51300.23020.94380.050*
H36B0.70830.27590.97710.050*
H36C0.64040.12981.04710.050*
C370.6854 (4)0.0579 (2)0.8514 (3)0.0382 (6)
H37A0.68580.01800.92970.046*
H37B0.76440.03900.78270.046*
H37C0.54710.08070.83270.046*
C381.0673 (4)0.0461 (3)0.9999 (3)0.0400 (6)
H38A1.21200.04980.99990.048*
H38B1.03530.03781.00170.048*
H38C0.99540.05831.07410.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0368 (14)0.0362 (14)0.0410 (14)0.0119 (12)0.0027 (12)0.0008 (11)
C20.0408 (15)0.0293 (12)0.0300 (12)0.0043 (11)0.0053 (11)0.0017 (10)
C30.0263 (11)0.0230 (10)0.0267 (11)0.0040 (9)0.0076 (9)0.0072 (8)
C40.0209 (10)0.0267 (10)0.0264 (11)0.0050 (9)0.0047 (9)0.0120 (9)
C50.0225 (11)0.0218 (10)0.0285 (11)0.0006 (8)0.0034 (9)0.0102 (9)
C60.0203 (11)0.0370 (12)0.0299 (11)0.0003 (9)0.0019 (9)0.0157 (10)
C70.0284 (12)0.0357 (12)0.0332 (12)0.0061 (10)0.0033 (10)0.0218 (10)
C80.0318 (13)0.0232 (10)0.0393 (13)0.0039 (10)0.0097 (11)0.0140 (9)
C90.0394 (14)0.0421 (14)0.0264 (12)0.0051 (12)0.0052 (11)0.0133 (10)
C100.0498 (16)0.0412 (14)0.0228 (11)0.0002 (12)0.0049 (11)0.0095 (10)
C110.0341 (13)0.0313 (12)0.0248 (11)0.0061 (10)0.0103 (10)0.0105 (9)
C120.0371 (14)0.0355 (13)0.0363 (13)0.0070 (11)0.0111 (11)0.0207 (11)
C130.0322 (13)0.0280 (12)0.0499 (15)0.0009 (10)0.0113 (12)0.0167 (11)
C140.0235 (12)0.0325 (12)0.0338 (12)0.0051 (10)0.0023 (10)0.0064 (10)
C150.0235 (11)0.0335 (12)0.0308 (12)0.0026 (9)0.0044 (9)0.0166 (10)
C160.0256 (11)0.0235 (10)0.0310 (11)0.0057 (9)0.0109 (9)0.0112 (9)
C170.0297 (12)0.0311 (11)0.0288 (11)0.0061 (10)0.0073 (10)0.0152 (9)
O170.0314 (9)0.0337 (9)0.0254 (8)0.0098 (7)0.0074 (7)0.0152 (7)
C180.0325 (13)0.0247 (11)0.0390 (13)0.0067 (10)0.0148 (11)0.0127 (10)
O180.0337 (9)0.0242 (8)0.0361 (9)0.0076 (7)0.0142 (8)0.0114 (7)
C190.0327 (12)0.0283 (11)0.0242 (10)0.0048 (9)0.0062 (9)0.0115 (9)
O190.0480 (11)0.0551 (12)0.0352 (9)0.0209 (10)0.0187 (9)0.0280 (9)
C200.0302 (12)0.0246 (10)0.0224 (10)0.0011 (9)0.0057 (9)0.0105 (8)
O200.0298 (9)0.0314 (8)0.0320 (8)0.0038 (7)0.0092 (7)0.0162 (7)
C210.0351 (13)0.0289 (11)0.0282 (11)0.0008 (10)0.0002 (10)0.0070 (9)
C220.0312 (12)0.0328 (12)0.0296 (12)0.0011 (10)0.0058 (10)0.0106 (10)
C230.0244 (11)0.0246 (10)0.0272 (11)0.0020 (9)0.0012 (9)0.0107 (9)
C240.0255 (11)0.0280 (11)0.0296 (11)0.0011 (9)0.0016 (9)0.0102 (9)
O240.0336 (9)0.0415 (10)0.0354 (9)0.0025 (8)0.0111 (8)0.0154 (8)
C250.0247 (11)0.0244 (10)0.0252 (11)0.0016 (9)0.0023 (9)0.0112 (8)
C260.0337 (13)0.0369 (13)0.0358 (12)0.0026 (11)0.0063 (11)0.0215 (11)
C270.0283 (12)0.0316 (12)0.0301 (11)0.0035 (10)0.0017 (10)0.0099 (9)
C280.0307 (13)0.0277 (11)0.0426 (14)0.0034 (10)0.0041 (11)0.0153 (10)
C290.0316 (12)0.0211 (10)0.0252 (10)0.0014 (9)0.0054 (9)0.0070 (8)
O290.0377 (10)0.0285 (8)0.0413 (10)0.0036 (7)0.0158 (8)0.0136 (8)
C300.0282 (11)0.0210 (10)0.0267 (11)0.0014 (9)0.0068 (9)0.0085 (8)
O300.0375 (10)0.0231 (8)0.0475 (10)0.0002 (7)0.0170 (8)0.0120 (7)
C310.0299 (13)0.0453 (14)0.0283 (12)0.0051 (11)0.0011 (10)0.0132 (11)
C320.0296 (12)0.0346 (12)0.0376 (13)0.0069 (10)0.0029 (10)0.0177 (10)
C330.0283 (12)0.0224 (10)0.0298 (11)0.0033 (9)0.0078 (9)0.0079 (9)
C340.0294 (12)0.0294 (12)0.0405 (13)0.0039 (10)0.0117 (11)0.0150 (10)
O340.0480 (12)0.0417 (11)0.0691 (14)0.0060 (9)0.0308 (11)0.0288 (10)
C350.0272 (11)0.0236 (10)0.0238 (10)0.0019 (9)0.0050 (9)0.0070 (8)
C360.0374 (14)0.0552 (17)0.0305 (13)0.0071 (13)0.0028 (11)0.0155 (12)
C370.0363 (14)0.0258 (12)0.0495 (15)0.0032 (11)0.0103 (12)0.0089 (11)
C380.0417 (15)0.0345 (13)0.0378 (14)0.0070 (12)0.0164 (12)0.0049 (11)
Geometric parameters (Å, º) top
C1—C141.520 (3)C21—C221.548 (4)
C1—C21.575 (4)C21—H21A0.9900
C1—H1A0.9900C21—H21B0.9900
C1—H1B0.9900C22—C231.558 (3)
C2—C31.512 (3)C22—H22A0.9900
C2—H2A0.9900C22—H22B0.9900
C2—H2B0.9900C23—C281.510 (3)
C3—C81.397 (3)C23—C241.518 (3)
C3—C41.407 (3)C23—C251.559 (3)
C4—C51.399 (3)C24—O241.205 (3)
C4—C171.505 (3)C25—C261.526 (3)
C5—C61.395 (3)C25—C271.538 (3)
C5—H50.9500C26—H26A0.9800
C6—C71.388 (3)C26—H26B0.9800
C6—C91.511 (3)C26—H26C0.9800
C7—C81.380 (4)C27—H27A0.9800
C7—H70.9500C27—H27B0.9800
C8—H80.9500C27—H27C0.9800
C9—C101.598 (4)C28—H28A0.9800
C9—H9A0.9900C28—H28B0.9800
C9—H9B0.9900C28—H28C0.9800
C10—C111.521 (4)C29—O291.210 (3)
C10—H10A0.9900C29—C301.504 (3)
C10—H10B0.9900C30—O301.459 (3)
C11—C121.394 (3)C30—C311.541 (3)
C11—C161.401 (3)C30—C351.557 (3)
C12—C131.392 (4)O30—C341.364 (3)
C12—H120.9500C31—C321.544 (3)
C13—C141.386 (4)C31—H31A0.9900
C13—H130.9500C31—H31B0.9900
C14—C151.392 (3)C32—C331.558 (3)
C15—C161.388 (3)C32—H32A0.9900
C15—H150.9500C32—H32B0.9900
C16—C181.508 (3)C33—C341.511 (3)
C17—O171.467 (3)C33—C381.517 (3)
C17—H17A0.9900C33—C351.558 (3)
C17—H17B0.9900C34—O341.201 (3)
O17—C191.333 (3)C35—C361.522 (3)
C18—O181.477 (3)C35—C371.524 (3)
C18—H18A0.9900C36—H36A0.9800
C18—H18B0.9900C36—H36B0.9800
O18—C291.330 (3)C36—H36C0.9800
C19—O191.202 (3)C37—H37A0.9800
C19—C201.509 (3)C37—H37B0.9800
C20—O201.460 (3)C37—H37C0.9800
C20—C211.538 (3)C38—H38A0.9800
C20—C251.559 (3)C38—H38B0.9800
O20—C241.363 (3)C38—H38C0.9800
C14—C1—C2114.1 (2)C23—C22—H22A111.0
C14—C1—H1A108.7C21—C22—H22B111.0
C2—C1—H1A108.7C23—C22—H22B111.0
C14—C1—H1B108.7H22A—C22—H22B109.0
C2—C1—H1B108.7C28—C23—C24113.9 (2)
H1A—C1—H1B107.6C28—C23—C22115.87 (19)
C3—C2—C1112.8 (2)C24—C23—C22103.53 (19)
C3—C2—H2A109.0C28—C23—C25119.6 (2)
C1—C2—H2A109.0C24—C23—C2599.17 (18)
C3—C2—H2B109.0C22—C23—C25102.27 (19)
C1—C2—H2B109.0O24—C24—O20121.6 (2)
H2A—C2—H2B107.8O24—C24—C23130.8 (2)
C8—C3—C4116.4 (2)O20—C24—C23107.52 (19)
C8—C3—C2119.1 (2)C26—C25—C27109.3 (2)
C4—C3—C2123.0 (2)C26—C25—C23114.97 (19)
C5—C4—C3119.8 (2)C27—C25—C23113.48 (19)
C5—C4—C17118.4 (2)C26—C25—C20114.46 (18)
C3—C4—C17121.8 (2)C27—C25—C20112.70 (18)
C6—C5—C4121.1 (2)C23—C25—C2091.09 (17)
C6—C5—H5119.4C25—C26—H26A109.5
C4—C5—H5119.4C25—C26—H26B109.5
C7—C6—C5116.6 (2)H26A—C26—H26B109.5
C7—C6—C9120.4 (2)C25—C26—H26C109.5
C5—C6—C9122.2 (2)H26A—C26—H26C109.5
C8—C7—C6121.0 (2)H26B—C26—H26C109.5
C8—C7—H7119.5C25—C27—H27A109.5
C6—C7—H7119.5C25—C27—H27B109.5
C7—C8—C3121.2 (2)H27A—C27—H27B109.5
C7—C8—H8119.4C25—C27—H27C109.5
C3—C8—H8119.4H27A—C27—H27C109.5
C6—C9—C10113.3 (2)H27B—C27—H27C109.5
C6—C9—H9A108.9C23—C28—H28A109.5
C10—C9—H9A108.9C23—C28—H28B109.5
C6—C9—H9B108.9H28A—C28—H28B109.5
C10—C9—H9B108.9C23—C28—H28C109.5
H9A—C9—H9B107.7H28A—C28—H28C109.5
C11—C10—C9112.5 (2)H28B—C28—H28C109.5
C11—C10—H10A109.1O29—C29—O18125.3 (2)
C9—C10—H10A109.1O29—C29—C30120.9 (2)
C11—C10—H10B109.1O18—C29—C30113.7 (2)
C9—C10—H10B109.1O30—C30—C29111.95 (18)
H10A—C10—H10B107.8O30—C30—C31105.2 (2)
C12—C11—C16116.8 (2)C29—C30—C31116.25 (19)
C12—C11—C10120.0 (2)O30—C30—C35102.18 (17)
C16—C11—C10121.6 (2)C29—C30—C35115.79 (19)
C13—C12—C11121.2 (2)C31—C30—C35104.00 (18)
C13—C12—H12119.4C34—O30—C30106.50 (17)
C11—C12—H12119.4C30—C31—C32101.49 (18)
C14—C13—C12120.3 (2)C30—C31—H31A111.5
C14—C13—H13119.8C32—C31—H31A111.5
C12—C13—H13119.8C30—C31—H31B111.5
C13—C14—C15117.0 (2)C32—C31—H31B111.5
C13—C14—C1122.5 (2)H31A—C31—H31B109.3
C15—C14—C1119.3 (2)C31—C32—C33104.00 (19)
C16—C15—C14121.5 (2)C31—C32—H32A111.0
C16—C15—H15119.2C33—C32—H32A111.0
C14—C15—H15119.2C31—C32—H32B111.0
C15—C16—C11119.9 (2)C33—C32—H32B111.0
C15—C16—C18117.5 (2)H32A—C32—H32B109.0
C11—C16—C18122.3 (2)C34—C33—C38114.7 (2)
O17—C17—C4109.78 (18)C34—C33—C32103.25 (19)
O17—C17—H17A109.7C38—C33—C32116.0 (2)
C4—C17—H17A109.7C34—C33—C3599.14 (18)
O17—C17—H17B109.7C38—C33—C35118.8 (2)
C4—C17—H17B109.7C32—C33—C35102.52 (19)
H17A—C17—H17B108.2O34—C34—O30122.0 (2)
C19—O17—C17115.01 (18)O34—C34—C33130.7 (2)
O18—C18—C16106.69 (19)O30—C34—C33107.3 (2)
O18—C18—H18A110.4C36—C35—C37109.7 (2)
C16—C18—H18A110.4C36—C35—C30112.1 (2)
O18—C18—H18B110.4C37—C35—C30114.73 (19)
C16—C18—H18B110.4C36—C35—C33113.5 (2)
H18A—C18—H18B108.6C37—C35—C33114.6 (2)
C29—O18—C18114.83 (18)C30—C35—C3391.31 (17)
O19—C19—O17124.7 (2)C35—C36—H36A109.5
O19—C19—C20122.3 (2)C35—C36—H36B109.5
O17—C19—C20112.93 (19)H36A—C36—H36B109.5
O20—C20—C19111.00 (18)C35—C36—H36C109.5
O20—C20—C21106.02 (19)H36A—C36—H36C109.5
C19—C20—C21115.87 (19)H36B—C36—H36C109.5
O20—C20—C25102.61 (16)C35—C37—H37A109.5
C19—C20—C25116.3 (2)C35—C37—H37B109.5
C21—C20—C25103.71 (18)H37A—C37—H37B109.5
C24—O20—C20106.11 (17)C35—C37—H37C109.5
C20—C21—C22101.45 (18)H37A—C37—H37C109.5
C20—C21—H21A111.5H37B—C37—H37C109.5
C22—C21—H21A111.5C33—C38—H38A109.5
C20—C21—H21B111.5C33—C38—H38B109.5
C22—C21—H21B111.5H38A—C38—H38B109.5
H21A—C21—H21B109.3C33—C38—H38C109.5
C21—C22—C23103.79 (18)H38A—C38—H38C109.5
C21—C22—H22A111.0H38B—C38—H38C109.5
C14—C1—C2—C39.9 (3)C28—C23—C24—O20164.18 (19)
C1—C2—C3—C866.9 (3)C22—C23—C24—O2069.1 (2)
C1—C2—C3—C498.9 (3)C25—C23—C24—O2036.0 (2)
C8—C3—C4—C516.3 (3)C28—C23—C25—C2666.8 (3)
C2—C3—C4—C5149.8 (2)C24—C23—C25—C26168.89 (19)
C8—C3—C4—C17165.4 (2)C22—C23—C25—C2662.8 (2)
C2—C3—C4—C1728.5 (3)C28—C23—C25—C2760.0 (3)
C3—C4—C5—C61.7 (3)C24—C23—C25—C2764.3 (2)
C17—C4—C5—C6180.0 (2)C22—C23—C25—C27170.39 (19)
C4—C5—C6—C714.4 (3)C28—C23—C25—C20175.4 (2)
C4—C5—C6—C9155.5 (2)C24—C23—C25—C2051.13 (18)
C5—C6—C7—C815.8 (4)C22—C23—C25—C2054.98 (19)
C9—C6—C7—C8154.3 (2)O20—C20—C25—C26170.92 (19)
C6—C7—C8—C31.0 (4)C19—C20—C25—C2667.7 (3)
C4—C3—C8—C715.2 (4)C21—C20—C25—C2660.7 (2)
C2—C3—C8—C7151.5 (2)O20—C20—C25—C2763.4 (2)
C7—C6—C9—C1072.6 (3)C19—C20—C25—C2758.0 (3)
C5—C6—C9—C1096.9 (3)C21—C20—C25—C27173.6 (2)
C6—C9—C10—C117.1 (3)O20—C20—C25—C2352.72 (18)
C9—C10—C11—C1293.2 (3)C19—C20—C25—C23174.06 (19)
C9—C10—C11—C1671.8 (3)C21—C20—C25—C2357.5 (2)
C16—C11—C12—C1314.7 (4)C18—O18—C29—O291.5 (3)
C10—C11—C12—C13151.0 (3)C18—O18—C29—C30179.89 (19)
C11—C12—C13—C140.3 (4)O29—C29—C30—O30176.8 (2)
C12—C13—C14—C1514.3 (4)O18—C29—C30—O304.5 (3)
C12—C13—C14—C1153.5 (3)O29—C29—C30—C3155.9 (3)
C2—C1—C14—C1397.1 (3)O18—C29—C30—C31125.4 (2)
C2—C1—C14—C1570.5 (3)O29—C29—C30—C3566.6 (3)
C13—C14—C15—C1614.6 (4)O18—C29—C30—C35112.0 (2)
C1—C14—C15—C16153.6 (2)C29—C30—O30—C34158.5 (2)
C14—C15—C16—C110.1 (4)C31—C30—O30—C3474.4 (2)
C14—C15—C16—C18173.0 (2)C35—C30—O30—C3434.0 (2)
C12—C11—C16—C1514.4 (3)O30—C30—C31—C3269.3 (2)
C10—C11—C16—C15151.0 (2)C29—C30—C31—C32166.2 (2)
C12—C11—C16—C18172.8 (2)C35—C30—C31—C3237.7 (2)
C10—C11—C16—C1821.8 (4)C30—C31—C32—C331.5 (2)
C5—C4—C17—O1787.5 (3)C31—C32—C33—C3467.9 (2)
C3—C4—C17—O1790.7 (3)C31—C32—C33—C38165.8 (2)
C4—C17—O17—C19169.00 (19)C31—C32—C33—C3534.8 (2)
C15—C16—C18—O1899.8 (2)C30—O30—C34—O34179.8 (3)
C11—C16—C18—O1887.3 (3)C30—O30—C34—C331.7 (3)
C16—C18—O18—C29166.57 (19)C38—C33—C34—O3417.8 (4)
C17—O17—C19—O191.6 (3)C32—C33—C34—O34109.4 (3)
C17—O17—C19—C20177.01 (19)C35—C33—C34—O34145.3 (3)
O19—C19—C20—O20170.7 (2)C38—C33—C34—O30163.9 (2)
O17—C19—C20—O2010.7 (3)C32—C33—C34—O3069.0 (2)
O19—C19—C20—C2149.7 (3)C35—C33—C34—O3036.3 (2)
O17—C19—C20—C21131.7 (2)O30—C30—C35—C3663.6 (2)
O19—C19—C20—C2572.5 (3)C29—C30—C35—C3658.4 (3)
O17—C19—C20—C25106.1 (2)C31—C30—C35—C36172.8 (2)
C19—C20—O20—C24159.30 (18)O30—C30—C35—C37170.41 (19)
C21—C20—O20—C2474.1 (2)C29—C30—C35—C3767.7 (3)
C25—C20—O20—C2434.4 (2)C31—C30—C35—C3761.1 (3)
O20—C20—C21—C2269.5 (2)O30—C30—C35—C3352.50 (19)
C19—C20—C21—C22166.9 (2)C29—C30—C35—C33174.43 (19)
C25—C20—C21—C2238.2 (2)C31—C30—C35—C3356.8 (2)
C20—C21—C22—C231.6 (2)C34—C33—C35—C3663.3 (2)
C21—C22—C23—C28167.0 (2)C38—C33—C35—C3661.4 (3)
C21—C22—C23—C2467.6 (2)C32—C33—C35—C36169.2 (2)
C21—C22—C23—C2535.1 (2)C34—C33—C35—C37169.6 (2)
C20—O20—C24—O24179.1 (2)C38—C33—C35—C3765.6 (3)
C20—O20—C24—C231.2 (2)C32—C33—C35—C3763.7 (2)
C28—C23—C24—O2418.2 (4)C34—C33—C35—C3051.53 (19)
C22—C23—C24—O24108.5 (3)C38—C33—C35—C30176.3 (2)
C25—C23—C24—O24146.5 (3)C32—C33—C35—C3054.34 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C22—H22A···O19i0.992.563.493 (4)157
C32—H32A···O29i0.992.443.381 (3)159
C17—H17A···O24ii0.992.583.442 (3)146
C27—H27A···O24ii0.982.513.486 (3)171
C9—H9A···O30ii0.992.593.556 (3)167
C36—H36A···O34ii0.982.543.503 (4)167
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z.
 

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