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The title compound, C40H58O4.CH2Cl2, was isolated for the first time from Bruguiera cyl­indrica (Rhizophoraceae), and for the first time from natural product resources. The structure contains five fused six-membered rings, with two rings in chair, two in twist-boat and one in a slightly twisted boat conformation. The D and E rings are cis-fused. The feruloyl substituent group is axially attached to the skeleton. O—H...O hydrogen bonds and C—H...O interactions are observed in the structure. The absolute configuration was established on the basis of anomalous scattering effects of the solvent.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803024838/ci6298sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803024838/ci6298Isup2.hkl
Contains datablock I

CCDC reference: 227781

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • Disorder in solvent or counterion
  • R factor = 0.062
  • wR factor = 0.152
  • Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT214_ALERT_2_C Atom Cl2A (Anion/Solvent) ADP max/min Ratio 4.60 prolat PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.19 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.94 Ratio PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C22 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C20 PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... C41 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 20.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
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 26.00 From the CIF: _reflns_number_total 7198 Count of symmetry unique reflns 4046 Completeness (_total/calc) 177.90% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 3152 Fraction of Friedel pairs measured 0.779 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

3α-feruloyltaraxerol dicholomethane top
Crystal data top
C40H58O4·CH2Cl2F(000) = 744
Mr = 687.79Dx = 1.188 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 4263 reflections
a = 12.5558 (10) Åθ = 2.3–26.0°
b = 8.5131 (7) ŵ = 0.21 mm1
c = 18.6076 (15) ÅT = 293 K
β = 104.834 (1)°Needle, colourless
V = 1922.7 (3) Å30.48 × 0.18 × 0.14 mm
Z = 2
Data collection top
Siemens SMART CCD area-detector
diffractometer
7198 independent reflections
Radiation source: fine-focus sealed tube5897 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
Detector resolution: 8.33 pixels mm-1θmax = 26.0°, θmin = 2.3°
ω scansh = 1515
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 910
Tmin = 0.907, Tmax = 0.972l = 1422
10423 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.062H-atom parameters constrained
wR(F2) = 0.152 w = 1/[σ2(Fo2) + (0.0698P)2 + 0.5197P]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max = 0.002
7198 reflectionsΔρmax = 0.34 e Å3
445 parametersΔρmin = 0.48 e Å3
5 restraintsAbsolute structure: Flack (1983), 3171 Friedel pairs'
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.12 (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
xyzUiso*/UeqOcc. (<1)
O10.35353 (18)0.2592 (3)0.22768 (11)0.0382 (5)
O20.37018 (19)0.4218 (3)0.32612 (12)0.0450 (6)
O30.5202 (2)0.7599 (3)0.51810 (13)0.0522 (7)
O40.7350 (2)0.8035 (4)0.57168 (13)0.0607 (8)
H40.68270.82310.58910.091*
C10.1745 (3)0.1292 (4)0.10527 (17)0.0340 (7)
H1A0.11050.15070.06460.041*
H1B0.23870.17020.09170.041*
C20.1617 (3)0.2137 (4)0.17470 (17)0.0407 (8)
H2A0.09380.17960.18560.049*
H2B0.15580.32570.16490.049*
C30.2569 (2)0.1840 (4)0.24230 (16)0.0346 (7)
H30.24060.23320.28590.042*
C40.2830 (2)0.0088 (4)0.25879 (16)0.0336 (7)
C50.2854 (2)0.0794 (4)0.18556 (16)0.0290 (6)
H50.34950.03620.17160.035*
C60.3094 (3)0.2554 (4)0.19597 (16)0.0353 (7)
H6A0.36890.27190.24020.042*
H6B0.24460.30920.20280.042*
C70.3416 (3)0.3240 (4)0.12843 (16)0.0332 (7)
H7A0.41060.27710.12530.040*
H7B0.35390.43600.13610.040*
C80.2554 (2)0.2984 (3)0.05384 (15)0.0266 (6)
C90.2221 (2)0.1219 (3)0.04805 (16)0.0263 (6)
H90.29010.06610.04730.032*
C100.1871 (2)0.0505 (3)0.11636 (15)0.0278 (6)
C110.1411 (2)0.0815 (4)0.02777 (16)0.0328 (7)
H11A0.15840.02280.04260.039*
H11B0.06700.07820.02120.039*
C120.1430 (2)0.1963 (4)0.09079 (16)0.0299 (7)
H12A0.09170.28100.08980.036*
H12B0.11720.14190.13780.036*
C130.2565 (2)0.2677 (3)0.08733 (16)0.0279 (6)
C140.3061 (2)0.3385 (3)0.01079 (16)0.0280 (6)
C150.3909 (3)0.4357 (4)0.00383 (18)0.0411 (8)
H150.42760.47180.04310.049*
C160.4284 (3)0.4882 (5)0.0698 (2)0.0533 (10)
H16A0.46910.40430.08600.064*
H16B0.47700.57800.05650.064*
C170.3276 (3)0.5333 (4)0.1335 (2)0.0465 (9)
C180.2424 (2)0.3949 (4)0.15068 (16)0.0298 (7)
H180.17030.44320.15470.036*
C190.2360 (3)0.3231 (4)0.22709 (17)0.0388 (8)
H19A0.18150.23970.23580.047*
H19B0.30660.27550.22590.047*
C200.2065 (3)0.4376 (5)0.29293 (19)0.0439 (8)
C210.2732 (4)0.5895 (6)0.2726 (2)0.0744 (14)
H21A0.30260.62030.31390.089*
H21B0.22470.67260.26460.089*
C220.3681 (4)0.5714 (7)0.2030 (2)0.0775 (15)
H22A0.41040.66810.19450.093*
H22B0.41660.48810.21090.093*
C230.3955 (3)0.0039 (4)0.31497 (17)0.0424 (8)
H23A0.45160.03520.29290.064*
H23B0.39520.05710.35830.064*
H23C0.41040.11180.32890.064*
C240.1978 (3)0.0574 (5)0.29771 (18)0.0480 (9)
H24A0.21240.16680.30840.072*
H24B0.20300.00120.34320.072*
H24C0.12500.04530.26570.072*
C250.1580 (3)0.4133 (4)0.05062 (18)0.0384 (7)
H25A0.17950.51770.04060.058*
H25B0.13900.41200.09740.058*
H25C0.09550.38130.01180.058*
C260.0757 (3)0.1179 (4)0.12368 (18)0.0383 (8)
H26A0.03060.14430.07530.057*
H26B0.08890.21040.15420.057*
H26C0.03870.04070.14610.057*
C270.3332 (3)0.1314 (4)0.09778 (18)0.0355 (7)
H27A0.33990.05670.05820.053*
H27B0.40470.17250.09700.053*
H27C0.30260.08060.14460.053*
C280.2731 (5)0.6777 (5)0.1092 (3)0.0795 (15)
H28A0.21040.70790.14830.119*
H28B0.32510.76270.09890.119*
H28C0.24980.65310.06520.119*
C290.0843 (3)0.4737 (7)0.3137 (3)0.0842 (17)
H29A0.06740.54490.35500.126*
H29B0.06450.52100.27200.126*
H29C0.04340.37820.32700.126*
C300.2361 (5)0.3619 (6)0.3595 (2)0.0795 (15)
H30A0.31320.33670.34670.119*
H30B0.21990.43370.40060.119*
H30C0.19370.26760.37300.119*
C310.4049 (3)0.3703 (4)0.27585 (17)0.0341 (7)
C320.5073 (3)0.4164 (4)0.25695 (17)0.0362 (7)
H320.51200.38630.20980.043*
C330.5938 (3)0.4943 (4)0.29666 (17)0.0376 (8)
H330.64930.50260.27200.045*
C340.6243 (3)0.5710 (4)0.36997 (17)0.0349 (7)
C350.7353 (3)0.5997 (4)0.40096 (19)0.0445 (8)
H350.78620.56820.37530.053*
C360.7722 (3)0.6734 (5)0.46841 (19)0.0505 (9)
H360.84740.68720.48870.061*
C370.6985 (3)0.7267 (4)0.50606 (18)0.0433 (8)
C380.5856 (3)0.6998 (4)0.47619 (17)0.0388 (8)
C390.5490 (3)0.6232 (4)0.40924 (17)0.0372 (7)
H390.47400.60580.38980.045*
C400.4073 (3)0.7209 (5)0.4989 (2)0.0575 (11)
H40A0.37220.76890.53350.086*
H40B0.37350.75840.44960.086*
H40C0.39920.60890.50030.086*
Cl10.00947 (18)0.4337 (3)0.27051 (12)0.1425 (7)
Cl2A0.0589 (19)0.449 (3)0.4384 (5)0.27 (2)0.216 (4)
Cl2B0.0808 (7)0.3423 (8)0.4237 (3)0.159 (3)0.529 (11)
Cl2C0.0216 (11)0.481 (4)0.4253 (5)0.194 (11)0.255 (12)
C410.0800 (6)0.4714 (10)0.3480 (5)0.155 (3)
H41A0.10150.58010.34470.186*0.216 (4)
H41B0.14430.40860.34760.186*0.216 (4)
H41C0.06590.57400.36490.186*0.529 (11)
H41D0.15150.47360.33840.186*0.529 (11)
H41E0.12250.56080.34050.186*0.255 (12)
H41F0.12930.38360.36050.186*0.255 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0467 (13)0.0375 (13)0.0336 (11)0.0013 (10)0.0162 (10)0.0088 (10)
O20.0572 (14)0.0483 (14)0.0362 (12)0.0027 (12)0.0242 (11)0.0074 (11)
O30.0522 (15)0.0652 (17)0.0427 (14)0.0070 (13)0.0183 (12)0.0202 (13)
O40.0567 (16)0.089 (2)0.0383 (14)0.0168 (15)0.0154 (12)0.0181 (14)
C10.0339 (16)0.0370 (19)0.0294 (16)0.0116 (14)0.0050 (13)0.0033 (13)
C20.0471 (19)0.0376 (19)0.0380 (17)0.0115 (16)0.0118 (15)0.0045 (15)
C30.0397 (17)0.0418 (19)0.0253 (15)0.0027 (15)0.0134 (13)0.0032 (14)
C40.0327 (16)0.0405 (19)0.0277 (15)0.0027 (14)0.0079 (13)0.0008 (14)
C50.0289 (15)0.0286 (16)0.0315 (15)0.0025 (13)0.0113 (12)0.0023 (13)
C60.0381 (17)0.0357 (19)0.0286 (15)0.0060 (14)0.0021 (13)0.0106 (14)
C70.0380 (16)0.0254 (16)0.0344 (16)0.0083 (13)0.0058 (13)0.0047 (13)
C80.0278 (14)0.0218 (15)0.0299 (15)0.0000 (12)0.0069 (12)0.0038 (12)
C90.0207 (13)0.0258 (15)0.0329 (15)0.0002 (12)0.0076 (12)0.0055 (12)
C100.0266 (14)0.0286 (16)0.0287 (15)0.0050 (12)0.0082 (12)0.0030 (12)
C110.0331 (16)0.0324 (17)0.0314 (15)0.0076 (14)0.0054 (12)0.0000 (13)
C120.0290 (15)0.0323 (17)0.0261 (15)0.0021 (13)0.0027 (12)0.0017 (13)
C130.0247 (14)0.0269 (16)0.0319 (15)0.0019 (12)0.0071 (12)0.0032 (13)
C140.0253 (14)0.0216 (15)0.0361 (16)0.0032 (12)0.0064 (12)0.0023 (12)
C150.0385 (18)0.045 (2)0.0362 (17)0.0130 (16)0.0036 (14)0.0015 (15)
C160.0427 (19)0.063 (3)0.053 (2)0.0276 (19)0.0086 (17)0.0049 (19)
C170.050 (2)0.037 (2)0.051 (2)0.0089 (16)0.0103 (16)0.0133 (16)
C180.0279 (15)0.0275 (16)0.0362 (16)0.0060 (12)0.0123 (13)0.0030 (13)
C190.0433 (18)0.0399 (19)0.0364 (17)0.0078 (15)0.0160 (14)0.0072 (15)
C200.0414 (18)0.053 (2)0.0400 (18)0.0120 (17)0.0157 (15)0.0134 (17)
C210.097 (3)0.066 (3)0.057 (2)0.020 (3)0.012 (2)0.026 (2)
C220.075 (3)0.095 (4)0.059 (3)0.041 (3)0.012 (2)0.024 (3)
C230.049 (2)0.047 (2)0.0296 (16)0.0062 (16)0.0080 (15)0.0012 (15)
C240.060 (2)0.058 (2)0.0317 (17)0.0014 (19)0.0220 (16)0.0057 (17)
C250.0464 (19)0.0293 (17)0.0406 (18)0.0078 (15)0.0129 (15)0.0033 (14)
C260.0341 (17)0.044 (2)0.0373 (17)0.0018 (15)0.0103 (14)0.0008 (15)
C270.0400 (18)0.0312 (17)0.0361 (17)0.0085 (14)0.0114 (14)0.0068 (14)
C280.105 (4)0.029 (2)0.091 (3)0.007 (2)0.001 (3)0.003 (2)
C290.055 (3)0.134 (5)0.062 (3)0.022 (3)0.012 (2)0.042 (3)
C300.123 (4)0.083 (4)0.038 (2)0.033 (3)0.031 (2)0.019 (2)
C310.0453 (18)0.0307 (17)0.0279 (16)0.0103 (14)0.0121 (14)0.0101 (14)
C320.0437 (18)0.0347 (18)0.0312 (16)0.0097 (15)0.0117 (14)0.0004 (14)
C330.0415 (18)0.0403 (19)0.0352 (17)0.0094 (15)0.0175 (15)0.0054 (15)
C340.0431 (18)0.0328 (17)0.0299 (16)0.0011 (14)0.0114 (13)0.0074 (14)
C350.046 (2)0.050 (2)0.0435 (19)0.0004 (16)0.0213 (16)0.0013 (17)
C360.0413 (18)0.069 (3)0.041 (2)0.0067 (18)0.0097 (16)0.0016 (18)
C370.053 (2)0.049 (2)0.0284 (16)0.0073 (17)0.0108 (15)0.0029 (15)
C380.0500 (19)0.0383 (19)0.0300 (16)0.0016 (15)0.0135 (14)0.0017 (14)
C390.0393 (17)0.0345 (18)0.0382 (18)0.0029 (14)0.0105 (14)0.0046 (14)
C400.057 (2)0.070 (3)0.055 (2)0.005 (2)0.0318 (19)0.018 (2)
Cl10.1454 (16)0.1149 (14)0.1460 (16)0.0114 (13)0.0015 (13)0.0218 (13)
Cl2A0.21 (2)0.41 (4)0.115 (10)0.25 (3)0.104 (13)0.148 (17)
Cl2B0.133 (5)0.251 (8)0.101 (3)0.057 (5)0.042 (3)0.057 (4)
Cl2C0.075 (6)0.39 (3)0.101 (8)0.099 (11)0.001 (7)0.028 (12)
C410.125 (6)0.128 (7)0.221 (10)0.037 (5)0.061 (7)0.065 (7)
Geometric parameters (Å, º) top
O1—C311.349 (4)C20—C211.535 (6)
O1—C31.457 (4)C21—C221.527 (6)
O2—C311.211 (4)C21—H21A0.97
O3—C381.369 (4)C21—H21B0.97
O3—C401.410 (4)C22—H22A0.97
O4—C371.357 (4)C22—H22B0.97
O4—H40.82C23—H23A0.96
C1—C21.523 (4)C23—H23B0.96
C1—C101.546 (4)C23—H23C0.96
C1—H1A0.97C24—H24A0.96
C1—H1B0.97C24—H24B0.96
C2—C31.518 (4)C24—H24C0.96
C2—H2A0.97C25—H25A0.96
C2—H2B0.97C25—H25B0.96
C3—C41.542 (5)C25—H25C0.96
C3—H30.98C26—H26A0.96
C4—C231.531 (4)C26—H26B0.96
C4—C241.543 (4)C26—H26C0.96
C4—C51.563 (4)C27—H27A0.96
C5—C61.530 (4)C27—H27B0.96
C5—C101.558 (4)C27—H27C0.96
C5—H50.98C28—H28A0.96
C6—C71.531 (4)C28—H28B0.96
C6—H6A0.97C28—H28C0.96
C6—H6B0.97C29—H29A0.96
C7—C81.541 (4)C29—H29B0.96
C7—H7A0.97C29—H29C0.96
C7—H7B0.97C30—H30A0.96
C8—C141.536 (4)C30—H30B0.96
C8—C251.555 (4)C30—H30C0.96
C8—C91.556 (4)C31—C321.470 (4)
C9—C111.552 (4)C32—C331.324 (5)
C9—C101.570 (4)C32—H320.93
C9—H90.98C33—C341.472 (5)
C10—C261.549 (4)C33—H330.93
C11—C121.532 (4)C34—C351.386 (5)
C11—H11A0.97C34—C391.407 (4)
C11—H11B0.97C35—C361.373 (5)
C12—C131.535 (4)C35—H350.93
C12—H12A0.97C36—C371.373 (5)
C12—H12B0.97C36—H360.93
C13—C141.525 (4)C37—C381.403 (5)
C13—C271.552 (4)C38—C391.377 (5)
C13—C181.577 (4)C39—H390.93
C14—C151.328 (4)C40—H40A0.96
C15—C161.491 (5)C40—H40B0.96
C15—H150.93C40—H40C0.96
C16—C171.545 (5)Cl1—C411.617 (9)
C16—H16A0.97Cl2A—C411.780 (12)
C16—H16B0.97Cl2A—H41C1.7526
C17—C281.530 (6)Cl2B—C411.785 (10)
C17—C221.541 (5)Cl2B—H41F1.4974
C17—C181.568 (4)Cl2C—C411.777 (11)
C18—C191.531 (4)Cl2C—H41C1.5866
C18—H180.98C41—H41A0.97
C19—C201.535 (5)C41—H41B0.97
C19—H19A0.97C41—H41C0.96
C19—H19B0.97C41—H41D0.96
C20—C291.515 (5)C41—H41E0.96
C20—C301.524 (5)C41—H41F0.96
C31—O1—C3117.6 (2)C29—C20—C19110.7 (3)
C38—O3—C40118.6 (3)C30—C20—C19108.7 (3)
C37—O4—H4109.5C21—C20—C19109.5 (3)
C2—C1—C10112.6 (3)C22—C21—C20112.5 (3)
C2—C1—H1A109.1C22—C21—H21A109.1
C10—C1—H1A109.1C20—C21—H21A109.1
C2—C1—H1B109.1C22—C21—H21B109.1
C10—C1—H1B109.1C20—C21—H21B109.1
H1A—C1—H1B107.8H21A—C21—H21B107.8
C3—C2—C1113.1 (3)C21—C22—C17112.3 (3)
C3—C2—H2A109.0C21—C22—H22A109.1
C1—C2—H2A109.0C17—C22—H22A109.1
C3—C2—H2B109.0C21—C22—H22B109.1
C1—C2—H2B109.0C17—C22—H22B109.1
H2A—C2—H2B107.8H22A—C22—H22B107.9
O1—C3—C2106.8 (2)C4—C23—H23A109.5
O1—C3—C4108.5 (2)C4—C23—H23B109.5
C2—C3—C4114.1 (3)H23A—C23—H23B109.5
O1—C3—H3109.1C4—C23—H23C109.5
C2—C3—H3109.1H23A—C23—H23C109.5
C4—C3—H3109.1H23B—C23—H23C109.5
C23—C4—C3108.4 (3)C4—C24—H24A109.5
C23—C4—C24106.5 (3)C4—C24—H24B109.5
C3—C4—C24108.0 (3)H24A—C24—H24B109.5
C23—C4—C5109.9 (2)C4—C24—H24C109.5
C3—C4—C5110.0 (2)H24A—C24—H24C109.5
C24—C4—C5113.8 (3)H24B—C24—H24C109.5
C6—C5—C10110.4 (2)C8—C25—H25A109.5
C6—C5—C4114.0 (2)C8—C25—H25B109.5
C10—C5—C4117.2 (2)H25A—C25—H25B109.5
C6—C5—H5104.6C8—C25—H25C109.5
C10—C5—H5104.6H25A—C25—H25C109.5
C4—C5—H5104.6H25B—C25—H25C109.5
C5—C6—C7110.8 (2)C10—C26—H26A109.5
C5—C6—H6A109.5C10—C26—H26B109.5
C7—C6—H6A109.5H26A—C26—H26B109.5
C5—C6—H6B109.5C10—C26—H26C109.5
C7—C6—H6B109.5H26A—C26—H26C109.5
H6A—C6—H6B108.1H26B—C26—H26C109.5
C6—C7—C8114.4 (2)C13—C27—H27A109.5
C6—C7—H7A108.7C13—C27—H27B109.5
C8—C7—H7A108.7H27A—C27—H27B109.5
C6—C7—H7B108.7C13—C27—H27C109.5
C8—C7—H7B108.7H27A—C27—H27C109.5
H7A—C7—H7B107.6H27B—C27—H27C109.5
C14—C8—C7109.7 (2)C17—C28—H28A109.5
C14—C8—C25108.0 (2)C17—C28—H28B109.5
C7—C8—C25108.0 (2)H28A—C28—H28B109.5
C14—C8—C9108.5 (2)C17—C28—H28C109.5
C7—C8—C9108.3 (2)H28A—C28—H28C109.5
C25—C8—C9114.2 (2)H28B—C28—H28C109.5
C11—C9—C8112.3 (2)C20—C29—H29A109.5
C11—C9—C10113.3 (2)C20—C29—H29B109.5
C8—C9—C10116.3 (2)H29A—C29—H29B109.5
C11—C9—H9104.5C20—C29—H29C109.5
C8—C9—H9104.5H29A—C29—H29C109.5
C10—C9—H9104.5H29B—C29—H29C109.5
C1—C10—C26108.3 (2)C20—C30—H30A109.5
C1—C10—C5107.4 (2)C20—C30—H30B109.5
C26—C10—C5114.2 (2)H30A—C30—H30B109.5
C1—C10—C9108.4 (2)C20—C30—H30C109.5
C26—C10—C9112.0 (2)H30A—C30—H30C109.5
C5—C10—C9106.3 (2)H30B—C30—H30C109.5
C12—C11—C9114.8 (2)O2—C31—O1124.2 (3)
C12—C11—H11A108.6O2—C31—C32126.7 (3)
C9—C11—H11A108.6O1—C31—C32109.1 (3)
C12—C11—H11B108.6C33—C32—C31130.0 (3)
C9—C11—H11B108.6C33—C32—H32115.0
H11A—C11—H11B107.5C31—C32—H32115.0
C11—C12—C13114.6 (2)C32—C33—C34136.1 (3)
C11—C12—H12A108.6C32—C33—H33111.9
C13—C12—H12A108.6C34—C33—H33111.9
C11—C12—H12B108.6C35—C34—C39117.8 (3)
C13—C12—H12B108.6C35—C34—C33117.4 (3)
H12A—C12—H12B107.6C39—C34—C33124.8 (3)
C14—C13—C12110.4 (2)C36—C35—C34122.0 (3)
C14—C13—C27107.1 (2)C36—C35—H35119.0
C12—C13—C27107.3 (2)C34—C35—H35119.0
C14—C13—C18111.6 (2)C37—C36—C35120.2 (3)
C12—C13—C18108.4 (2)C37—C36—H36119.9
C27—C13—C18112.0 (2)C35—C36—H36119.9
C15—C14—C13117.5 (3)O4—C37—C36120.2 (3)
C15—C14—C8123.0 (3)O4—C37—C38120.6 (3)
C13—C14—C8119.5 (2)C36—C37—C38119.2 (3)
C14—C15—C16121.4 (3)O3—C38—C39125.7 (3)
C14—C15—H15119.3O3—C38—C37114.0 (3)
C16—C15—H15119.3C39—C38—C37120.4 (3)
C15—C16—C17109.6 (3)C38—C39—C34120.4 (3)
C15—C16—H16A109.7C38—C39—H39119.8
C17—C16—H16A109.7C34—C39—H39119.8
C15—C16—H16B109.7O3—C40—H40A109.5
C17—C16—H16B109.7O3—C40—H40B109.5
H16A—C16—H16B108.2H40A—C40—H40B109.5
C28—C17—C22110.3 (4)O3—C40—H40C109.5
C28—C17—C16108.2 (3)H40A—C40—H40C109.5
C22—C17—C16108.3 (3)H40B—C40—H40C109.5
C28—C17—C18109.3 (3)Cl1—C41—Cl2A125.8 (7)
C22—C17—C18110.0 (3)Cl1—C41—Cl2B116.3 (5)
C16—C17—C18110.6 (3)Cl1—C41—Cl2C113.3 (6)
C19—C18—C17111.1 (3)Cl1—C41—H41A105.9
C19—C18—C13112.9 (3)Cl1—C41—H41B105.9
C17—C18—C13115.1 (2)Cl1—C41—H41C109.2
C19—C18—H18105.6Cl1—C41—H41D107.9
C17—C18—H18105.6Cl1—C41—H41E108.3
C13—C18—H18105.6Cl1—C41—H41F108.6
C18—C19—C20115.6 (3)Cl2A—C41—H41A105.9
C18—C19—H19A108.4Cl2A—C41—H41B105.9
C20—C19—H19A108.4H41A—C41—H41B106.2
C18—C19—H19B108.4Cl2B—C41—H41C105.4
C20—C19—H19B108.4Cl2B—C41—H41D110.1
H19A—C19—H19B107.4H41C—C41—H41D107.7
C29—C20—C30108.7 (4)Cl2C—C41—H41E116.1
C29—C20—C21110.2 (4)Cl2C—C41—H41F102.3
C30—C20—C21109.0 (3)H41E—C41—H41F107.8
C10—C1—C2—C357.4 (4)C25—C8—C14—C1593.3 (3)
C31—O1—C3—C2121.4 (3)C9—C8—C14—C15142.4 (3)
C31—O1—C3—C4115.2 (3)C7—C8—C14—C13157.2 (2)
C1—C2—C3—O167.4 (3)C25—C8—C14—C1385.3 (3)
C1—C2—C3—C452.5 (4)C9—C8—C14—C1339.1 (3)
O1—C3—C4—C2347.4 (3)C13—C14—C15—C166.7 (5)
C2—C3—C4—C23166.3 (2)C8—C14—C15—C16171.9 (3)
O1—C3—C4—C24162.4 (2)C14—C15—C16—C1744.5 (5)
C2—C3—C4—C2478.7 (3)C15—C16—C17—C2865.8 (4)
O1—C3—C4—C572.8 (3)C15—C16—C17—C22174.6 (4)
C2—C3—C4—C546.1 (3)C15—C16—C17—C1854.0 (4)
C23—C4—C5—C661.4 (3)C28—C17—C18—C19129.1 (3)
C3—C4—C5—C6179.4 (2)C22—C17—C18—C197.8 (4)
C24—C4—C5—C658.0 (3)C16—C17—C18—C19111.8 (3)
C23—C4—C5—C10167.6 (3)C28—C17—C18—C13101.0 (3)
C3—C4—C5—C1048.3 (3)C22—C17—C18—C13137.7 (3)
C24—C4—C5—C1073.1 (3)C16—C17—C18—C1318.1 (4)
C10—C5—C6—C761.2 (3)C14—C13—C18—C19158.0 (2)
C4—C5—C6—C7164.4 (2)C12—C13—C18—C1980.3 (3)
C5—C6—C7—C856.6 (3)C27—C13—C18—C1937.9 (3)
C6—C7—C8—C14167.6 (3)C14—C13—C18—C1729.0 (3)
C6—C7—C8—C2574.9 (3)C12—C13—C18—C17150.7 (3)
C6—C7—C8—C949.3 (3)C27—C13—C18—C1791.1 (3)
C14—C8—C9—C1157.1 (3)C17—C18—C19—C2057.0 (4)
C7—C8—C9—C11176.1 (2)C13—C18—C19—C20172.0 (3)
C25—C8—C9—C1163.5 (3)C18—C19—C20—C2977.1 (4)
C14—C8—C9—C10170.0 (2)C18—C19—C20—C30163.5 (3)
C7—C8—C9—C1051.0 (3)C18—C19—C20—C2144.6 (4)
C25—C8—C9—C1069.4 (3)C29—C20—C21—C22136.0 (4)
C2—C1—C10—C2669.0 (3)C30—C20—C21—C22104.8 (4)
C2—C1—C10—C554.8 (3)C19—C20—C21—C2214.0 (5)
C2—C1—C10—C9169.3 (2)C20—C21—C22—C1762.6 (6)
C6—C5—C10—C1175.0 (2)C28—C17—C22—C2171.7 (5)
C4—C5—C10—C152.3 (3)C16—C17—C22—C21170.0 (4)
C6—C5—C10—C2664.8 (3)C18—C17—C22—C2149.0 (5)
C4—C5—C10—C2667.9 (3)C3—O1—C31—O27.3 (4)
C6—C5—C10—C959.1 (3)C3—O1—C31—C32172.8 (2)
C4—C5—C10—C9168.1 (2)O2—C31—C32—C3316.1 (6)
C11—C9—C10—C156.1 (3)O1—C31—C32—C33164.0 (3)
C8—C9—C10—C1171.5 (2)C31—C32—C33—C343.2 (7)
C11—C9—C10—C2663.4 (3)C32—C33—C34—C35161.1 (4)
C8—C9—C10—C2669.0 (3)C32—C33—C34—C3921.8 (6)
C11—C9—C10—C5171.3 (2)C39—C34—C35—C361.4 (5)
C8—C9—C10—C556.3 (3)C33—C34—C35—C36178.7 (3)
C8—C9—C11—C1222.0 (3)C34—C35—C36—C372.6 (6)
C10—C9—C11—C12156.3 (2)C35—C36—C37—O4178.1 (4)
C9—C11—C12—C1333.8 (4)C35—C36—C37—C382.4 (6)
C11—C12—C13—C1452.0 (3)C40—O3—C38—C3910.8 (5)
C11—C12—C13—C2764.5 (3)C40—O3—C38—C37171.3 (3)
C11—C12—C13—C18174.4 (2)O4—C37—C38—O31.3 (5)
C12—C13—C14—C15164.7 (3)C36—C37—C38—O3179.2 (3)
C27—C13—C14—C1578.7 (3)O4—C37—C38—C39179.4 (3)
C18—C13—C14—C1544.2 (4)C36—C37—C38—C391.2 (5)
C12—C13—C14—C813.9 (4)O3—C38—C39—C34177.9 (3)
C27—C13—C14—C8102.6 (3)C37—C38—C39—C340.0 (5)
C18—C13—C14—C8134.5 (3)C35—C34—C39—C380.1 (5)
C7—C8—C14—C1524.2 (4)C33—C34—C39—C38177.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O30.822.192.651 (4)115
O4—H4···O2i0.822.042.768 (4)147
C3—H3···O20.982.272.724 (4)107
C39—H39···O20.932.182.932 (4)137
Symmetry code: (i) x+1, y1/2, z+1.
 

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