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Acta Cryst. (2007). E63, o3222
https://doi.org/10.1107/S1600536807028620
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The oxalate diester of dehydro­epi­androsterone

P. J. Cox, L. Nahar, S. D. Sarker and A. B. Turner
There are two independent mol­ecules of bis­(17-oxoandrost-5-en-3β-yl) oxalate, [or bis­(DHEA) oxalate], C40H54O6, in the asymmetric unit of the title compound. Molecules are held together by C—H...O hydrogen bonding. There is distortion in the central oxalate section of the mol­ecules and a short inter­molecular H...H contact of 2.14 Å is present.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807028620/pk2029sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807028620/pk2029Isup2.hkl
Contains datablock I

CCDC reference: 654964

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.041
  • wR factor = 0.101
  • Data-to-parameter ratio = 9.5

checkCIF/PLATON results

No syntax errors found




Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.767     0.990
            Tmin(prime) and Tmax expected:      0.968     0.990
            RR(prime) =      0.793
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.79
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C20    -   C40    ...       1.54 Ang.
PLAT411_ALERT_2_C Short Inter H...H Contact  H7A    ..  H61A    ..       2.14 Ang.


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           27.54
           From the CIF: _reflns_number_total               7977
           Count of symmetry unique reflns         8025
           Completeness (_total/calc)             99.40%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C23    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C28    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C29    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C30    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C33    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C34    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C43    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C48    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C49    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C50    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C53    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C54    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C63    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C68    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C69    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C70    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C73    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C74    = .          S
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1


   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
  26 ALERT level G = General alerts; check

  24 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
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check
Comment top

Crystal structures of DHEA forms have been published (Cox et al., 1990; Caira et al., 1995; Stahly et al., 2006) and details of the importance, uses, preparation and spectroscopic data of the title compound and related symmetrical steroidal dimers are available (Nahar et al., 2006). The atomic arrangement in the molecules of (I) are shown in Figures 1 & 2. There are no classical hydrogen bonds but weak C—H···O contacts hold the molecules together (Table 1). A short H61A···H7Ai contact of 2.14 Å is also present where C61···C7i=4.019 (4) Å and i indicates coordinates transformed by -1 + x, y, z. The length of the central Csp2—Csp2 bond appears to be different in the two independent molecules with C20—C40=1.542 (4) Å and C60—C80=1.521 (3) Å, but the difference is similar to the accuracy limitation for light atoms caused by the spherical-atom scattering factor approximation (Coppens et al., 1969). Long Csp2—Csp2 bonds are also present in perfluoromethyloxalate (Védova et al., 2004). The oxalate portions of the molecules deviate from planarity, as can be seen by the torsion angles. One oxalate moiety is considerably more non-planar than the other but the overall lengths of the molecules are similar (O3···O6=24.895 (3) Å and O13···O16=24.310 (3) Å). Differences in torsion angles are also evident in the two independent molecules, for example, the C13—C17 ring may be described as a C14 envelope whereas the C53—C57 ring conformation is twisted on C53—C54. The A, B and C ring conformations are chair, half-chair and chair, respectively.

Related literature top

For related literature, see: Caira et al. (1995); Coppens et al. (1969); Cox et al. (1990); Nahar et al. (2006); Stahly et al. (2006); Védova et al. (2004).

Experimental top

Details of the synthesis of (I) have have been published previously (Nahar et al., 2006).

Refinement top

All non-hydrogen atoms were refined by full-matrix least squares calculations with anisotropic displacement parameters. All the hydrogen atoms were allowed to ride on their attached atoms with isotropic displacement parameters 1.2 (non-methyl) or 1.3 (methyl) times those of the Ueq of their attached atoms. The constrained distances C—H distances were 0.95—1.00 Å.

Structure description top

Crystal structures of DHEA forms have been published (Cox et al., 1990; Caira et al., 1995; Stahly et al., 2006) and details of the importance, uses, preparation and spectroscopic data of the title compound and related symmetrical steroidal dimers are available (Nahar et al., 2006). The atomic arrangement in the molecules of (I) are shown in Figures 1 & 2. There are no classical hydrogen bonds but weak C—H···O contacts hold the molecules together (Table 1). A short H61A···H7Ai contact of 2.14 Å is also present where C61···C7i=4.019 (4) Å and i indicates coordinates transformed by -1 + x, y, z. The length of the central Csp2—Csp2 bond appears to be different in the two independent molecules with C20—C40=1.542 (4) Å and C60—C80=1.521 (3) Å, but the difference is similar to the accuracy limitation for light atoms caused by the spherical-atom scattering factor approximation (Coppens et al., 1969). Long Csp2—Csp2 bonds are also present in perfluoromethyloxalate (Védova et al., 2004). The oxalate portions of the molecules deviate from planarity, as can be seen by the torsion angles. One oxalate moiety is considerably more non-planar than the other but the overall lengths of the molecules are similar (O3···O6=24.895 (3) Å and O13···O16=24.310 (3) Å). Differences in torsion angles are also evident in the two independent molecules, for example, the C13—C17 ring may be described as a C14 envelope whereas the C53—C57 ring conformation is twisted on C53—C54. The A, B and C ring conformations are chair, half-chair and chair, respectively.

For related literature, see: Caira et al. (1995); Coppens et al. (1969); Cox et al. (1990); Nahar et al. (2006); Stahly et al. (2006); Védova et al. (2004).

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. View of molecule A (50% probability displacement ellipsoids)
[Figure 2] Fig. 2. View of molecule B (50% probability displacement ellipsoids)
Bis(17-oxoandrost-5-en-3β-yl) oxalate top
Crystal data top
C40H54O6F(000) = 1368
Mr = 630.83Dx = 1.236 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 7932 reflections
a = 10.9843 (2) Åθ = 2.9–27.5°
b = 22.8189 (4) ŵ = 0.08 mm−1
c = 13.5307 (3) ÅT = 120 K
β = 90.4679 (8)°Shard, colourless
V = 3391.35 (11) Å30.4 × 0.18 × 0.12 mm
Z = 4
Data collection top
Bruker Nonius KappaCCD area-detector
diffractometer		7977 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode6961 reflections with I > 2σ(I)
10cm confocal mirrors monochromatorRint = 0.052
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.0°
φ and ω scans to fill Ewald sphereh = −14→14
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		k = −26→29
Tmin = 0.767, Tmax = 0.990l = −17→17
47104 measured reflections
Refinement top
Refinement on F21 restraint
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.041 w = 1/[σ2(Fo2) + (0.04P)2 + 1.0704P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.101(Δ/σ)max = 0.001
S = 1.08Δρmax = 0.24 e Å−3
7977 reflectionsΔρmin = −0.21 e Å−3
837 parameters
Crystal data top
C40H54O6V = 3391.35 (11) Å3
Mr = 630.83Z = 4
Monoclinic, P21Mo Kα radiation
a = 10.9843 (2) ŵ = 0.08 mm−1
b = 22.8189 (4) ÅT = 120 K
c = 13.5307 (3) Å0.4 × 0.18 × 0.12 mm
β = 90.4679 (8)°
Data collection top
Bruker Nonius KappaCCD area-detector
diffractometer		7977 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		6961 reflections with I > 2σ(I)
Tmin = 0.767, Tmax = 0.990Rint = 0.052
47104 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0411 restraint
wR(F2) = 0.101H-atom parameters constrained
S = 1.08Δρmax = 0.24 e Å−3
7977 reflectionsΔρmin = −0.21 e Å−3
837 parameters
Special details top

Experimental. Please note cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su'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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.27654 (16)0.39110 (9)0.36696 (13)0.0268 (6)
O20.28360 (18)0.43998 (10)0.51126 (14)0.0362 (7)
O31.19833 (17)0.51255 (11)0.12127 (16)0.0386 (7)
O40.05853 (17)0.34398 (9)0.43152 (14)0.0327 (6)
O50.04748 (16)0.42369 (9)0.53081 (14)0.0296 (6)
O6−0.86836 (18)0.37757 (10)0.82784 (16)0.0406 (7)
C10.6213 (2)0.40740 (14)0.35944 (19)0.0294 (8)
C20.4984 (2)0.38118 (14)0.3902 (2)0.0316 (9)
C30.3967 (2)0.41569 (13)0.34180 (19)0.0251 (8)
C40.4067 (2)0.41395 (14)0.23054 (18)0.0262 (8)
C50.5293 (2)0.43738 (12)0.19843 (17)0.0221 (7)
C60.5344 (2)0.48089 (13)0.13302 (19)0.0257 (8)
C70.6504 (2)0.50557 (13)0.0928 (2)0.0271 (8)
C80.7619 (2)0.46846 (12)0.11729 (18)0.0219 (7)
C90.7578 (2)0.44600 (12)0.22445 (18)0.0225 (7)
C100.6417 (2)0.40917 (12)0.24610 (19)0.0229 (7)
C110.8770 (2)0.41332 (15)0.2528 (2)0.0318 (9)
C120.9939 (2)0.44914 (15)0.2334 (2)0.0337 (9)
C130.9951 (2)0.46925 (13)0.12583 (19)0.0254 (8)
C140.8782 (2)0.50416 (12)0.10579 (18)0.0238 (7)
C150.9032 (3)0.53751 (14)0.0095 (2)0.0305 (8)
C161.0359 (3)0.55726 (14)0.0245 (2)0.0346 (9)
C171.0928 (2)0.51328 (14)0.0959 (2)0.0292 (8)
C181.0131 (3)0.41725 (13)0.0542 (2)0.0335 (9)
C190.6546 (3)0.34619 (13)0.2067 (2)0.0347 (9)
C200.2320 (2)0.40929 (13)0.45218 (19)0.0256 (8)
C21−0.2313 (2)0.36090 (12)0.6565 (2)0.0261 (8)
C22−0.0959 (2)0.36558 (13)0.6295 (2)0.0278 (8)
C23−0.0816 (2)0.41334 (13)0.5541 (2)0.0265 (8)
C24−0.1270 (2)0.47188 (13)0.5924 (2)0.0286 (8)
C25−0.2568 (2)0.46788 (12)0.63014 (19)0.0243 (8)
C26−0.3393 (2)0.50685 (12)0.6018 (2)0.0261 (8)
C27−0.4682 (2)0.50860 (13)0.6363 (2)0.0269 (8)
C28−0.4901 (2)0.46943 (12)0.72601 (19)0.0228 (7)
C29−0.4245 (2)0.41036 (12)0.71200 (18)0.0210 (7)
C30−0.2845 (2)0.41768 (12)0.70134 (18)0.0220 (7)
C31−0.4610 (2)0.36478 (13)0.7901 (2)0.0272 (8)
C32−0.6000 (2)0.35675 (13)0.7984 (2)0.0270 (8)
C33−0.6596 (2)0.41564 (13)0.82002 (19)0.0250 (8)
C34−0.6263 (2)0.45853 (12)0.73764 (19)0.0239 (8)
C35−0.7150 (2)0.50985 (14)0.7496 (2)0.0312 (8)
C36−0.8352 (3)0.47724 (15)0.7706 (2)0.0363 (9)
C37−0.7986 (2)0.41702 (14)0.8101 (2)0.0302 (9)
C38−0.6304 (3)0.43788 (14)0.9247 (2)0.0320 (9)
C39−0.2229 (2)0.43014 (14)0.8021 (2)0.0310 (9)
C400.1011 (2)0.38720 (13)0.46887 (19)0.0252 (8)
O110.19740 (15)0.69236 (9)0.04788 (13)0.0263 (6)
O120.23972 (17)0.75414 (10)0.17391 (15)0.0359 (7)
O131.09475 (18)0.63291 (10)−0.28203 (18)0.0439 (8)
O14−0.02565 (18)0.75112 (11)0.04883 (15)0.0406 (7)
O15−0.01064 (15)0.73075 (9)0.21241 (13)0.0281 (6)
O16−0.95965 (19)0.62030 (11)0.37227 (19)0.0471 (8)
C410.4750 (2)0.62355 (12)−0.0640 (2)0.0252 (8)
C420.3415 (2)0.63001 (12)−0.0320 (2)0.0266 (8)
C430.3277 (2)0.68548 (12)0.02691 (19)0.0237 (7)
C440.3685 (2)0.73865 (12)−0.03119 (19)0.0248 (8)
C450.4977 (2)0.73165 (12)−0.06773 (18)0.0228 (7)
C460.5797 (2)0.77333 (12)−0.04915 (19)0.0242 (8)
C470.7093 (2)0.77187 (12)−0.08359 (19)0.0241 (8)
C480.7275 (2)0.72659 (12)−0.16549 (18)0.0214 (7)
C490.6651 (2)0.66863 (12)−0.13677 (19)0.0224 (7)
C500.5245 (2)0.67575 (12)−0.12449 (18)0.0215 (7)
C510.6985 (2)0.61734 (12)−0.2063 (2)0.0281 (8)
C520.8356 (2)0.61090 (13)−0.2273 (2)0.0286 (8)
C530.8873 (2)0.66922 (12)−0.26098 (19)0.0241 (7)
C540.8622 (2)0.71563 (12)−0.18203 (19)0.0240 (8)
C550.9464 (3)0.76702 (13)−0.2082 (2)0.0300 (8)
C561.0632 (3)0.73580 (15)−0.2404 (2)0.0368 (10)
C571.0258 (2)0.67288 (14)−0.2651 (2)0.0307 (9)
C580.8387 (2)0.68677 (14)−0.3647 (2)0.0314 (9)
C590.4586 (2)0.67877 (13)−0.22588 (19)0.0278 (8)
C600.1690 (2)0.72963 (13)0.11932 (19)0.0264 (8)
C61−0.3297 (2)0.67005 (14)0.1980 (2)0.0312 (8)
C62−0.1938 (2)0.67426 (14)0.1777 (2)0.0320 (9)
C63−0.1444 (2)0.73038 (13)0.22232 (19)0.0257 (8)
C64−0.1688 (2)0.73280 (14)0.33261 (19)0.0272 (8)
C65−0.3019 (2)0.72253 (12)0.35682 (18)0.0240 (7)
C66−0.3611 (2)0.75799 (12)0.41736 (19)0.0261 (8)
C67−0.4915 (2)0.75037 (13)0.4470 (2)0.0280 (8)
C68−0.5435 (2)0.69030 (12)0.42259 (19)0.0249 (8)
C69−0.5019 (2)0.67017 (12)0.31928 (19)0.0255 (8)
C70−0.3602 (2)0.66861 (12)0.3090 (2)0.0256 (8)
C71−0.5620 (3)0.61208 (14)0.2879 (3)0.0374 (10)
C72−0.7024 (3)0.61239 (14)0.2949 (3)0.0368 (10)
C73−0.7400 (2)0.63190 (13)0.3974 (2)0.0316 (9)
C74−0.6822 (2)0.69156 (12)0.42096 (19)0.0258 (8)
C75−0.7538 (2)0.71445 (15)0.5105 (2)0.0358 (10)
C76−0.8856 (3)0.69720 (17)0.4813 (2)0.0416 (10)
C77−0.8744 (3)0.64574 (14)0.4109 (2)0.0347 (9)
C78−0.7139 (3)0.58473 (16)0.4764 (3)0.0509 (13)
C79−0.3063 (3)0.61348 (13)0.3583 (3)0.0369 (10)
C800.0318 (2)0.73837 (13)0.12178 (19)0.0271 (8)
H1A0.687420.384140.390380.0353*
H1B0.627110.447810.385670.0353*
H2A0.493720.339640.369400.0379*
H2B0.490400.382830.462940.0379*
H30.400910.457330.364620.0302*
H4A0.340930.437890.200550.0314*
H4B0.396880.373110.207120.0314*
H60.459800.497330.110380.0308*
H7A0.662590.545440.119980.0326*
H7B0.642550.509080.020140.0326*
H80.764490.434170.071320.0262*
H90.753720.481430.267790.0270*
H11A0.874240.403020.323870.0381*
H11B0.880960.376300.214840.0381*
H12A0.996600.483650.277730.0404*
H12B1.066480.424680.247360.0404*
H140.875270.534750.158640.0286*
H15A0.847920.571490.001760.0366*
H15B0.894650.51160−0.048840.0366*
H16A1.079670.55719−0.039140.0415*
H16B1.039000.597280.052680.0415*
H18A1.016040.43187−0.013870.0435*
H18B0.945010.389780.060670.0435*
H18C1.089510.397140.070290.0435*
H19A0.575470.326460.208880.0451*
H19B0.713410.324690.247740.0451*
H19C0.683330.347340.138310.0451*
H21A−0.241380.328570.704570.0313*
H21B−0.278520.350690.596360.0313*
H22A−0.046780.374740.689180.0333*
H22B−0.067040.327860.602130.0333*
H23−0.127130.402660.492380.0318*
H24A−0.123590.501210.538530.0342*
H24B−0.072820.485410.646530.0342*
H26−0.314600.535990.556010.0313*
H27A−0.522560.495980.581600.0323*
H27B−0.489650.549470.653420.0323*
H28−0.457660.489180.786720.0275*
H29−0.454250.394560.647220.0252*
H31A−0.427940.377030.855180.0326*
H31B−0.423640.326630.773130.0326*
H32A−0.632980.340590.735790.0324*
H32B−0.618330.328740.852130.0324*
H34−0.652220.438670.675030.0287*
H35A−0.720920.533560.688480.0374*
H35B−0.691030.535470.805520.0374*
H36A−0.883700.498760.820140.0435*
H36B−0.884300.473250.709280.0435*
H38A−0.659350.409370.973340.0416*
H38B−0.671060.475570.935350.0416*
H38C−0.542230.442900.932260.0416*
H39A−0.137400.440550.791840.0403*
H39B−0.227540.395080.843730.0403*
H39C−0.264760.462690.834660.0403*
H41A0.482800.58743−0.103950.0302*
H41B0.526460.61866−0.004100.0302*
H42A0.287750.63139−0.091080.0320*
H42B0.317460.595880.008600.0320*
H430.375110.682550.090130.0285*
H44A0.313030.74449−0.088400.0297*
H44B0.363540.773880.011300.0297*
H460.554400.80625−0.011540.0291*
H47A0.763480.76230−0.027010.0289*
H47B0.732320.81112−0.108400.0289*
H480.689930.74162−0.228110.0257*
H490.698000.65795−0.070040.0269*
H51A0.668870.58037−0.176740.0337*
H51B0.654880.62282−0.269990.0337*
H52A0.878640.59775−0.166710.0344*
H52B0.848000.58101−0.279310.0344*
H540.894490.69916−0.118550.0288*
H55A0.911610.79092−0.262540.0360*
H55B0.961510.79246−0.150080.0360*
H56A1.098200.75524−0.299140.0441*
H56B1.124600.73626−0.186460.0441*
H58A0.859680.65623−0.412580.0408*
H58B0.875670.72397−0.384720.0408*
H58C0.750030.69121−0.362450.0408*
H59A0.374670.69206−0.216560.0362*
H59B0.458190.63982−0.256360.0362*
H59C0.501340.70636−0.268940.0362*
H61A−0.362120.634110.166390.0374*
H61B−0.371250.704050.167270.0374*
H62A−0.151110.640130.207030.0384*
H62B−0.179630.674030.105550.0384*
H63−0.180890.765220.188400.0308*
H64A−0.118580.702740.366430.0327*
H64B−0.143820.771640.358300.0327*
H66−0.317940.790540.443840.0313*
H67A−0.541360.780600.413310.0336*
H67B−0.497910.757010.519090.0336*
H68−0.514890.661390.473230.0299*
H69−0.531860.700500.271590.0306*
H71A−0.529580.580210.330200.0449*
H71B−0.538900.603310.218880.0449*
H72A−0.736960.639420.244780.0442*
H72B−0.734440.572590.281510.0442*
H74−0.705320.717740.364580.0309*
H75A−0.745160.757410.518050.0430*
H75B−0.727640.694940.572510.0430*
H76A−0.932450.685860.540460.0498*
H76B−0.927510.730410.448430.0498*
H78A−0.626720.575480.477120.0659*
H78B−0.760520.549270.460830.0659*
H78C−0.737710.599490.541430.0659*
H79A−0.217270.616240.359260.0480*
H79B−0.331200.578680.320790.0480*
H79C−0.336170.610440.426130.0480*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0197 (9)0.0364 (11)0.0244 (9)−0.0019 (8)0.0038 (7)−0.0033 (8)
O20.0299 (10)0.0544 (14)0.0244 (10)−0.0097 (10)0.0017 (8)−0.0066 (10)
O30.0220 (10)0.0502 (13)0.0435 (12)−0.0050 (10)0.0004 (8)0.0017 (11)
O40.0283 (10)0.0373 (12)0.0325 (10)−0.0045 (9)0.0070 (8)−0.0079 (9)
O50.0213 (9)0.0330 (11)0.0346 (10)−0.0022 (8)0.0063 (7)−0.0072 (9)
O60.0275 (11)0.0478 (14)0.0466 (13)−0.0087 (10)0.0064 (9)−0.0022 (11)
C10.0220 (13)0.0395 (16)0.0267 (13)0.0033 (12)0.0003 (10)0.0087 (12)
C20.0242 (14)0.0409 (17)0.0296 (14)−0.0009 (12)0.0028 (11)0.0080 (13)
C30.0189 (12)0.0326 (15)0.0239 (12)−0.0028 (11)0.0018 (9)0.0005 (11)
C40.0196 (12)0.0370 (16)0.0220 (12)0.0013 (11)0.0007 (9)−0.0013 (11)
C50.0197 (12)0.0269 (14)0.0198 (12)0.0018 (10)−0.0005 (9)−0.0061 (10)
C60.0202 (12)0.0330 (15)0.0238 (13)0.0060 (11)−0.0025 (10)−0.0024 (11)
C70.0250 (13)0.0285 (15)0.0278 (13)0.0023 (12)−0.0032 (10)0.0044 (12)
C80.0203 (12)0.0232 (13)0.0221 (12)−0.0003 (10)0.0000 (9)−0.0006 (10)
C90.0166 (11)0.0281 (14)0.0229 (12)0.0026 (10)0.0002 (9)−0.0027 (11)
C100.0196 (12)0.0248 (14)0.0244 (12)0.0026 (10)0.0013 (9)0.0004 (11)
C110.0202 (12)0.0437 (18)0.0314 (14)0.0030 (12)0.0027 (10)0.0148 (13)
C120.0209 (13)0.0488 (19)0.0313 (15)0.0019 (13)0.0013 (11)0.0088 (13)
C130.0192 (12)0.0293 (14)0.0277 (13)−0.0015 (11)0.0021 (10)0.0006 (12)
C140.0236 (12)0.0251 (14)0.0228 (12)−0.0019 (11)0.0000 (10)−0.0006 (11)
C150.0284 (14)0.0314 (15)0.0316 (15)−0.0022 (12)−0.0003 (11)0.0077 (12)
C160.0290 (15)0.0353 (16)0.0396 (16)−0.0100 (13)0.0022 (12)0.0049 (13)
C170.0253 (13)0.0342 (16)0.0280 (14)−0.0023 (12)0.0036 (10)−0.0048 (12)
C180.0299 (14)0.0283 (16)0.0423 (16)0.0024 (12)0.0095 (12)−0.0015 (13)
C190.0282 (14)0.0264 (15)0.0497 (18)0.0010 (12)0.0081 (13)−0.0022 (14)
C200.0234 (12)0.0313 (15)0.0221 (12)0.0017 (12)0.0006 (10)0.0017 (11)
C210.0264 (13)0.0257 (14)0.0262 (13)0.0011 (11)0.0057 (10)−0.0008 (11)
C220.0252 (13)0.0289 (15)0.0293 (14)0.0056 (11)0.0049 (10)−0.0046 (11)
C230.0181 (12)0.0327 (15)0.0289 (14)−0.0018 (11)0.0052 (10)−0.0048 (12)
C240.0229 (13)0.0270 (15)0.0358 (15)−0.0023 (11)0.0037 (11)−0.0009 (12)
C250.0224 (12)0.0261 (14)0.0245 (13)−0.0013 (11)0.0019 (10)−0.0046 (11)
C260.0250 (13)0.0227 (14)0.0307 (14)−0.0006 (11)0.0011 (10)0.0038 (12)
C270.0217 (12)0.0261 (14)0.0329 (14)0.0033 (11)−0.0007 (10)0.0006 (12)
C280.0183 (12)0.0250 (14)0.0252 (12)0.0022 (10)−0.0011 (9)−0.0017 (11)
C290.0198 (12)0.0238 (13)0.0193 (11)0.0000 (10)−0.0010 (9)−0.0016 (10)
C300.0188 (12)0.0240 (14)0.0231 (12)0.0019 (10)−0.0008 (9)−0.0006 (10)
C310.0257 (13)0.0284 (15)0.0275 (13)0.0031 (11)0.0049 (10)0.0016 (11)
C320.0261 (13)0.0310 (15)0.0240 (13)−0.0030 (12)0.0041 (10)−0.0002 (11)
C330.0213 (12)0.0310 (15)0.0227 (12)−0.0014 (11)−0.0003 (9)−0.0044 (11)
C340.0194 (12)0.0290 (15)0.0233 (12)0.0013 (11)−0.0014 (9)−0.0037 (11)
C350.0246 (13)0.0315 (15)0.0374 (15)0.0035 (12)−0.0008 (11)−0.0013 (13)
C360.0211 (13)0.0431 (18)0.0447 (17)0.0042 (13)0.0035 (12)−0.0025 (14)
C370.0223 (13)0.0395 (17)0.0288 (14)−0.0004 (12)0.0056 (10)−0.0068 (12)
C380.0286 (14)0.0404 (17)0.0271 (14)0.0002 (13)0.0007 (11)−0.0059 (13)
C390.0221 (13)0.0448 (18)0.0262 (13)0.0026 (12)−0.0005 (10)−0.0042 (12)
C400.0225 (12)0.0319 (15)0.0213 (12)0.0036 (11)0.0024 (10)−0.0007 (11)
O110.0170 (8)0.0324 (11)0.0297 (10)−0.0020 (8)0.0053 (7)−0.0057 (8)
O120.0249 (10)0.0471 (13)0.0356 (11)−0.0023 (9)0.0026 (8)−0.0151 (10)
O130.0240 (11)0.0450 (14)0.0627 (15)0.0066 (10)0.0097 (10)0.0021 (11)
O140.0273 (10)0.0658 (16)0.0287 (10)0.0093 (10)0.0020 (8)0.0025 (10)
O150.0182 (9)0.0377 (11)0.0285 (10)0.0021 (8)0.0038 (7)−0.0011 (9)
O160.0244 (11)0.0451 (14)0.0717 (16)−0.0029 (10)−0.0026 (10)0.0037 (12)
C410.0222 (12)0.0206 (13)0.0328 (14)−0.0015 (11)0.0052 (10)−0.0004 (11)
C420.0207 (12)0.0251 (14)0.0342 (15)−0.0032 (11)0.0068 (10)0.0007 (12)
C430.0138 (11)0.0294 (14)0.0280 (13)−0.0010 (10)0.0041 (9)−0.0008 (11)
C440.0220 (12)0.0261 (14)0.0263 (13)0.0007 (11)0.0026 (10)−0.0024 (11)
C450.0213 (12)0.0258 (14)0.0213 (12)0.0012 (11)0.0018 (9)0.0006 (11)
C460.0252 (13)0.0226 (14)0.0249 (13)0.0021 (11)0.0004 (10)−0.0027 (11)
C470.0193 (12)0.0219 (13)0.0311 (14)−0.0026 (10)−0.0004 (10)0.0004 (11)
C480.0174 (11)0.0222 (13)0.0246 (12)−0.0024 (10)0.0008 (9)0.0023 (10)
C490.0194 (12)0.0231 (13)0.0247 (12)−0.0001 (10)0.0027 (9)0.0002 (10)
C500.0188 (11)0.0218 (13)0.0240 (12)−0.0018 (10)0.0015 (9)−0.0003 (10)
C510.0217 (12)0.0225 (14)0.0402 (15)−0.0036 (11)0.0099 (11)−0.0039 (12)
C520.0235 (13)0.0266 (15)0.0359 (15)0.0008 (11)0.0078 (11)−0.0022 (12)
C530.0177 (12)0.0281 (14)0.0266 (12)−0.0010 (11)0.0029 (9)0.0002 (11)
C540.0197 (12)0.0282 (15)0.0242 (13)−0.0017 (11)0.0032 (10)0.0032 (11)
C550.0252 (13)0.0297 (15)0.0352 (15)−0.0063 (12)0.0039 (11)0.0013 (12)
C560.0219 (13)0.0451 (19)0.0435 (17)−0.0101 (13)0.0072 (12)−0.0057 (14)
C570.0213 (13)0.0400 (17)0.0310 (14)−0.0016 (13)0.0057 (10)0.0026 (13)
C580.0250 (13)0.0420 (18)0.0273 (14)−0.0014 (13)0.0031 (10)−0.0007 (13)
C590.0230 (13)0.0326 (15)0.0279 (13)−0.0005 (12)0.0013 (10)−0.0047 (12)
C600.0232 (13)0.0330 (15)0.0229 (12)0.0014 (12)0.0028 (10)−0.0029 (12)
C610.0242 (13)0.0351 (16)0.0343 (15)−0.0017 (12)0.0043 (11)−0.0135 (13)
C620.0256 (14)0.0350 (17)0.0354 (15)0.0012 (12)0.0059 (11)−0.0117 (13)
C630.0167 (12)0.0317 (15)0.0287 (13)0.0023 (11)0.0027 (10)−0.0042 (12)
C640.0187 (12)0.0350 (16)0.0280 (13)0.0007 (11)0.0012 (10)−0.0028 (12)
C650.0212 (12)0.0288 (14)0.0221 (12)0.0012 (11)0.0022 (9)0.0010 (11)
C660.0251 (13)0.0259 (14)0.0273 (13)−0.0022 (11)0.0023 (10)−0.0020 (11)
C670.0243 (13)0.0332 (16)0.0265 (13)0.0014 (12)0.0057 (10)−0.0051 (11)
C680.0217 (12)0.0279 (14)0.0251 (13)0.0011 (11)−0.0002 (10)0.0032 (11)
C690.0204 (12)0.0257 (14)0.0305 (14)0.0010 (11)0.0015 (10)−0.0036 (11)
C700.0180 (12)0.0259 (14)0.0328 (14)0.0023 (11)0.0037 (10)−0.0052 (11)
C710.0270 (14)0.0320 (16)0.0534 (19)−0.0031 (13)0.0057 (13)−0.0102 (14)
C720.0245 (14)0.0333 (17)0.0527 (19)−0.0041 (13)−0.0005 (13)−0.0069 (14)
C730.0196 (13)0.0318 (16)0.0433 (17)−0.0025 (12)0.0014 (11)0.0084 (13)
C740.0219 (12)0.0288 (15)0.0267 (13)0.0015 (11)0.0009 (10)0.0050 (11)
C750.0241 (14)0.050 (2)0.0335 (15)0.0008 (13)0.0073 (11)0.0024 (14)
C760.0250 (14)0.057 (2)0.0430 (18)−0.0021 (15)0.0081 (12)−0.0005 (16)
C770.0240 (14)0.0361 (17)0.0440 (17)−0.0029 (13)0.0014 (12)0.0166 (14)
C780.0335 (17)0.0410 (19)0.078 (3)−0.0010 (15)−0.0039 (16)0.0278 (19)
C790.0264 (14)0.0273 (16)0.057 (2)0.0059 (12)0.0050 (13)0.0053 (14)
C800.0214 (12)0.0349 (16)0.0250 (13)0.0009 (12)0.0045 (10)−0.0039 (12)
Geometric parameters (Å, º) top
O1—C31.477 (3)C36—H36B0.9900
O1—C201.323 (3)C36—H36A0.9900
O2—C201.201 (3)C38—H38B0.9800
O3—C171.206 (3)C38—H38C0.9800
O4—C401.201 (3)C38—H38A0.9800
O5—C231.474 (3)C39—H39B0.9800
O5—C401.323 (3)C39—H39C0.9800
O6—C371.208 (4)C39—H39A0.9800
O11—C601.327 (3)C41—C421.540 (3)
O11—C431.470 (3)C41—C501.547 (4)
O12—C601.205 (3)C42—C431.504 (4)
O13—C571.209 (4)C43—C441.516 (4)
O14—C801.203 (3)C44—C451.515 (3)
O15—C801.327 (3)C45—C461.332 (4)
O15—C631.477 (3)C45—C501.519 (4)
O16—C771.216 (4)C46—C471.502 (3)
C1—C21.537 (3)C47—C481.529 (4)
C1—C101.552 (4)C48—C491.541 (4)
C2—C31.512 (4)C48—C541.519 (3)
C3—C41.511 (4)C49—C501.563 (3)
C4—C51.516 (3)C49—C511.548 (4)
C5—C61.332 (4)C50—C591.547 (3)
C5—C101.530 (3)C51—C521.542 (3)
C6—C71.499 (3)C52—C531.518 (4)
C7—C81.523 (3)C53—C541.531 (4)
C8—C141.524 (3)C53—C571.525 (3)
C8—C91.539 (3)C53—C581.550 (4)
C9—C111.552 (3)C54—C551.537 (4)
C9—C101.557 (3)C55—C561.534 (5)
C10—C191.540 (4)C56—C571.530 (5)
C11—C121.546 (4)C60—C801.521 (3)
C12—C131.526 (4)C61—C621.523 (3)
C13—C141.533 (3)C61—C701.542 (4)
C13—C171.527 (4)C62—C631.514 (4)
C13—C181.546 (4)C63—C641.519 (4)
C14—C151.536 (4)C64—C651.519 (3)
C15—C161.538 (5)C65—C661.326 (4)
C16—C171.524 (4)C65—C701.528 (4)
C20—C401.542 (3)C66—C671.501 (3)
C21—C221.538 (3)C67—C681.520 (4)
C21—C301.547 (4)C68—C691.544 (4)
C22—C231.502 (4)C68—C741.524 (3)
C23—C241.519 (4)C69—C701.564 (3)
C24—C251.521 (3)C69—C711.539 (4)
C25—C301.529 (4)C70—C791.540 (4)
C25—C261.324 (4)C71—C721.546 (5)
C26—C271.495 (3)C72—C731.517 (5)
C27—C281.528 (4)C73—C741.535 (4)
C28—C291.541 (4)C73—C771.522 (4)
C28—C341.526 (3)C73—C781.542 (5)
C29—C301.555 (3)C74—C751.541 (4)
C29—C311.538 (4)C75—C761.548 (4)
C30—C391.544 (4)C76—C771.518 (5)
C31—C321.543 (3)C41—H41A0.9900
C32—C331.524 (4)C41—H41B0.9900
C33—C381.536 (4)C42—H42A0.9900
C33—C341.530 (4)C42—H42B0.9900
C33—C371.532 (3)C43—H431.0000
C34—C351.533 (4)C44—H44A0.9900
C35—C361.544 (4)C44—H44B0.9900
C36—C371.527 (5)C46—H460.9500
C1—H1B0.9900C47—H47A0.9900
C1—H1A0.9900C47—H47B0.9900
C2—H2B0.9900C48—H481.0000
C2—H2A0.9900C49—H491.0000
C3—H31.0000C51—H51A0.9900
C4—H4B0.9900C51—H51B0.9900
C4—H4A0.9900C52—H52A0.9900
C6—H60.9500C52—H52B0.9900
C7—H7A0.9900C54—H541.0000
C7—H7B0.9900C55—H55A0.9900
C8—H81.0000C55—H55B0.9900
C9—H91.0000C56—H56A0.9900
C11—H11A0.9900C56—H56B0.9900
C11—H11B0.9900C58—H58A0.9800
C12—H12A0.9900C58—H58B0.9800
C12—H12B0.9900C58—H58C0.9800
C14—H141.0000C59—H59A0.9800
C15—H15B0.9900C59—H59B0.9800
C15—H15A0.9900C59—H59C0.9800
C16—H16A0.9900C61—H61A0.9900
C16—H16B0.9900C61—H61B0.9900
C18—H18A0.9800C62—H62A0.9900
C18—H18B0.9800C62—H62B0.9900
C18—H18C0.9800C63—H631.0000
C19—H19B0.9800C64—H64A0.9900
C19—H19A0.9800C64—H64B0.9900
C19—H19C0.9800C66—H660.9500
C21—H21B0.9900C67—H67A0.9900
C21—H21A0.9900C67—H67B0.9900
C22—H22B0.9900C68—H681.0000
C22—H22A0.9900C69—H691.0000
C23—H231.0000C71—H71A0.9900
C24—H24B0.9900C71—H71B0.9900
C24—H24A0.9900C72—H72A0.9900
C26—H260.9500C72—H72B0.9900
C27—H27A0.9900C74—H741.0000
C27—H27B0.9900C75—H75A0.9900
C28—H281.0000C75—H75B0.9900
C29—H291.0000C76—H76A0.9900
C31—H31A0.9900C76—H76B0.9900
C31—H31B0.9900C78—H78A0.9800
C32—H32A0.9900C78—H78B0.9800
C32—H32B0.9900C78—H78C0.9800
C34—H341.0000C79—H79A0.9800
C35—H35A0.9900C79—H79B0.9800
C35—H35B0.9900C79—H79C0.9800
O1···O42.773 (3)H19C···C113.0200
O2···C34i3.239 (3)H21A···C312.8100
O2···O52.636 (3)H21A···O12x2.3600
O2···C23.180 (3)H21A···H31B2.2100
O2···C78i3.337 (4)H21A···H39B2.4200
O4···C223.220 (3)H21B···H292.2900
O4···O12.773 (3)H21B···H232.4900
O5···O22.636 (3)H21B···H67Avii2.5500
O11···O142.793 (3)H22A···O6i2.7000
O12···O152.854 (3)H22A···C392.7800
O12···C21ii3.349 (3)H22A···H39A2.2800
O12···C443.145 (3)H22B···C402.9200
O14···C623.095 (3)H22B···H76Bvii2.3300
O14···O112.793 (3)H22B···O42.7200
O15···O122.854 (3)H23···H11Aiii2.2800
O1···H12Biii2.9100H23···O42.5800
O2···H78Bi2.6300H23···H1Aiii2.4900
O2···H2B2.7000H23···H21B2.4900
O2···H27Ai2.6500H24A···H262.2600
O2···H32.4100H24B···H39A2.3300
O2···H34i2.3200H24B···H36Bi2.2500
O3···H42Bi2.7700H24B···C36i3.1000
O3···H6i2.9000H24B···H52Bxi2.5600
O3···H72Biv2.6600H24B···C392.9700
O3···H4Ai2.5500H26···H24A2.2600
O4···H55Av2.6100H26···H79C2.4500
O4···H11Aiii2.8300H27A···H292.5900
O4···H58Bv2.9000H27A···H342.3200
O4···H22B2.7200H27A···H78A2.5600
O4···H232.5800H27A···O2iii2.6500
O5···H36Bi2.7600H27B···H51Bxi2.5200
O6···H18Avi2.7900H27B···H59Bxi2.4700
O6···H22Aiii2.7000H27B···C352.9500
O6···H63vii2.6300H28···H38C2.4300
O11···H16Biii2.7800H28···H39C2.2900
O12···H432.4900H28···H51Axi2.5500
O12···H72Ai2.8000H28···C382.9200
O12···H74i2.7700H28···C392.9200
O12···H44B2.6300H29···H21B2.2900
O12···H21Aii2.3600H29···C262.9200
O12···H31Bii2.7000H29···H2Biii2.5800
O13···H76Aviii2.7000H29···H342.4300
O14···H632.5700H29···H27A2.5900
O14···H55Biii2.8500H31A···C382.7900
O14···H47Aiii2.5400H31A···C392.6600
O14···H62B2.5600H31A···H39B2.2500
O14···H54iii2.7000H31A···H38C2.2200
O16···H79Aiii2.8400H31B···C212.7600
O16···H64Aiii2.5700H31B···O12x2.7000
C2···O23.180 (3)H31B···H21A2.2100
C6···C38ix3.479 (4)H32A···C65vii3.0500
C19···C44v3.423 (4)H32A···H342.3900
C21···O12x3.349 (3)H32A···C66vii2.8000
C22···O43.220 (3)H32B···H46x2.3200
C34···O2iii3.239 (3)H32B···H38A2.5100
C38···C6xi3.479 (4)H32B···C46x2.9800
C44···O123.145 (3)H34···H27A2.3200
C44···C19xii3.423 (4)H34···H292.4300
C62···O143.095 (3)H34···O2iii2.3200
C78···O2iii3.337 (4)H34···H32A2.3900
C1···H11A2.8300H35A···H78C2.5000
C2···H19A2.8900H35A···C272.9300
C2···H67Bx3.0900H35A···C783.1000
C4···H19A2.7400H35B···C382.8300
C6···H93.0100H35B···C42xi3.1000
C6···H38Cix2.9700H35B···H38B2.2400
C7···H15A2.9200H35B···H41Axi2.5500
C8···H18B2.8100H36A···H16Avi2.3600
C8···H19C2.9100H36B···H24Biii2.2500
C11···H19C3.0200H36B···O5iii2.7600
C11···H1A2.8800H36B···C24iii3.0900
C11···H19B2.7100H38A···H32B2.5100
C11···H18B2.7600H38B···C352.6700
C11···H143.0500H38B···C362.8600
C15···H7B2.9400H38B···H35B2.2400
C15···H7A3.0500H38C···C312.7800
C15···H52A2.7600H38C···H31A2.2200
C15···H18A2.7300H38C···C282.9200
C16···H18A2.9200H38C···H282.4300
C18···H15B2.8700H38C···C6xi2.9700
C18···H82.7700H39A···C222.8200
C18···H11B2.7800H39A···H24B2.3300
C19···H4B2.9000H39A···C242.7900
C19···H82.9800H39A···H22A2.2800
C19···H2A2.8400H39B···H31A2.2500
C19···H11B2.5800H39B···H21A2.4200
C19···H44Av2.8400H39B···C312.7500
C20···H2B2.9000H39C···H15Bxi2.6000
C21···H31B2.7600H39C···H282.2900
C22···H39A2.8200H39C···C282.8700
C24···H52Bxi3.0500H41A···C512.8400
C24···H39A2.7900H41A···H35Bix2.5500
C24···H36Bi3.0900H41A···H51A2.2800
C25···H52Bxi3.0800H41A···H59B2.4000
C26···H292.9200H41B···H432.5600
C27···H35A2.9300H41B···H492.2800
C28···H39C2.8700H42A···C592.8400
C28···H38C2.9200H42A···H44A2.6000
C31···H21A2.8100H42A···H59A2.4000
C31···H38C2.7800H42B···O3iii2.7700
C31···H39B2.7500H43···O122.4900
C35···H38B2.6700H43···H41B2.5600
C35···H27B2.9500H44A···C592.8800
C36···H38B2.8600H44A···H42A2.6000
C36···H24Biii3.1000H44A···H56Biii2.4600
C38···H35B2.8300H44A···H59A2.2200
C38···H31A2.7900H44A···C19xii2.8400
C38···H282.9200H44A···H19Cxii2.4400
C38···H6xi3.0200H44B···O122.6300
C39···H15Bxi3.0200H44B···C602.7900
C39···H31A2.6600H44B···H462.2500
C39···H24B2.9700H46···H44B2.2500
C39···H282.9200H46···H32Bii2.3200
C39···H22A2.7800H47A···O14i2.5400
C40···H22B2.9200H47A···H492.5500
C41···H51A2.8100H47A···H542.3900
C42···H35Bix3.1000H47B···C552.9000
C42···H59A2.9000H47B···H4Bxii2.4000
C44···H59A2.7300H48···C453.0500
C44···H19Cxii2.9300H48···C582.7800
C45···H483.0500H48···C592.9200
C45···H19Axii2.9900H48···H58C2.2500
C46···H492.9500H48···H59C2.2900
C46···H32Bii2.9800H49···C462.9500
C46···H19Axii3.0000H49···H41B2.2800
C47···H55B2.9600H49···H47A2.5500
C47···H4Bxii3.0800H49···H542.4500
C48···H59C2.8800H51A···C412.8100
C48···H58C2.8000H51A···H28ix2.5500
C51···H58C2.7700H51A···H41A2.2800
C51···H41A2.8400H51B···C582.8100
C51···H543.0800H51B···C592.5800
C51···H59B2.7700H51B···H27Bix2.5200
C51···H59C3.0800H51B···H58C2.2600
C55···H47B2.9000H51B···H59B2.2000
C55···H58B2.6900H51B···H59C2.5500
C56···H58B2.8400H52A···C152.7600
C57···H76Aviii2.6900H52A···H15A2.3800
C58···H76Aviii2.8300H52A···H15B2.5400
C58···H51B2.8100H52A···H542.4100
C58···H55A2.8600H52B···C24ix3.0500
C58···H482.7800H52B···C25ix3.0800
C59···H42A2.8400H52B···H24Bix2.5600
C59···H482.9200H52B···H58A2.4900
C59···H51B2.5800H54···O14i2.7000
C59···H44A2.8800H54···C513.0800
C60···H72Ai2.8600H54···H47A2.3900
C60···H44B2.7900H54···H492.4500
C61···H7Aiii3.0300H54···H52A2.4100
C61···H71B2.7700H55A···C582.8600
C62···H79A2.8000H55A···H58B2.2800
C64···H79A2.7400H55A···O4xii2.6100
C64···H76Bi3.0700H55B···O14i2.8500
C65···H32Axiii3.0500H55B···C472.9600
C66···H32Axiii2.8000H56B···H44Ai2.4600
C66···H693.0100H58A···H52B2.4900
C67···H75A2.9600H58A···H76Aviii2.4700
C68···H78A2.8700H58B···C552.6900
C68···H79C2.9200H58B···C562.8400
C71···H79C3.0900H58B···H55A2.2800
C71···H743.0700H58B···H76Aviii2.5000
C71···H61A2.8000H58B···O4xii2.9000
C71···H79B2.6800H58C···C482.8000
C71···H78A2.7900H58C···C512.7700
C75···H67B2.9800H58C···H482.2500
C75···H78C2.6600H58C···H51B2.2600
C75···H67A3.0800H59A···C422.9000
C76···H78C2.8700H59A···C442.7300
C76···H64Aiii2.9900H59A···H42A2.4000
C77···H64Aiii3.0400H59A···H44A2.2200
C78···H35A3.1000H59B···C512.7700
C78···H682.8000H59B···H27Bix2.4700
C78···H71A2.8400H59B···H41A2.4000
C78···H75B2.8400H59B···H51B2.2000
C79···H62A2.7400H59C···C482.8800
C79···H64A2.9000H59C···C513.0800
C79···H682.9900H59C···H482.2900
C79···H71A2.5900H59C···H51B2.5500
C80···H62B2.7500H61A···C712.8000
H1A···C112.8800H61A···H7Aiii2.1400
H1A···H11A2.2900H61A···H71B2.1900
H1A···H19B2.3800H61A···H79B2.4600
H1A···H23i2.4900H61B···H632.5300
H1B···H32.5100H61B···H692.2700
H1B···H92.2600H62A···C792.7400
H2A···C192.8400H62A···H14iii2.5100
H2A···H67Bx2.4200H62A···H79A2.2600
H2A···H19A2.3800H62B···O142.5600
H2A···H4B2.5500H62B···C802.7500
H2B···O22.7000H63···O142.5700
H2B···H29i2.5800H63···H61B2.5300
H2B···C202.9000H63···O6xiii2.6300
H3···O22.4100H64A···O16i2.5700
H3···H1B2.5100H64A···C76i2.9900
H4A···O3iii2.5500H64A···C77i3.0400
H4A···H62.2500H64A···C792.9000
H4B···H2A2.5500H64A···H76Bi2.4500
H4B···C192.9000H64A···H79A2.2500
H4B···H47Bv2.4000H64B···H662.2800
H4B···H19A2.2300H66···H64B2.2800
H4B···C47v3.0800H67A···C753.0800
H6···O3iii2.9000H67A···H742.3900
H6···C38ix3.0200H67A···H21Bxiii2.5500
H6···H4A2.2500H67B···C752.9800
H7A···C153.0500H67B···C2ii3.0900
H7A···H61Ai2.1400H67B···H2Aii2.4200
H7A···C61i3.0300H68···C782.8000
H7A···H142.4000H68···C792.9900
H7B···C152.9400H68···H78A2.3100
H8···C192.9800H68···H79C2.3700
H8···H18B2.2300H69···C663.0100
H8···H19C2.3600H69···H61B2.2700
H8···C182.7700H69···H742.3300
H9···H79Bi2.5100H71A···C782.8400
H9···C63.0100H71A···C792.5900
H9···H1B2.2600H71A···H78A2.2700
H9···H142.3400H71A···H79B2.1800
H11A···O4i2.8300H71A···H79C2.5700
H11A···C12.8300H71B···C612.7700
H11A···H1A2.2900H71B···H61A2.1900
H11A···H23i2.2800H72A···O12iii2.8000
H11B···H19C2.4900H72A···C60iii2.8600
H11B···C182.7800H72A···H742.4400
H11B···C192.5800H72B···O3xiv2.6600
H11B···H19B2.2300H72B···H78B2.5000
H11B···H18B2.2300H74···O12iii2.7700
H12A···H142.3900H74···C713.0700
H12B···H18C2.4900H74···H67A2.3900
H12B···O1i2.9100H74···H692.3300
H14···H7A2.4000H74···H72A2.4400
H14···H92.3400H75A···C672.9600
H14···H12A2.3900H75B···C782.8400
H14···H62Ai2.5100H75B···H78C2.2200
H14···C113.0500H76A···O13vi2.7000
H15A···C72.9200H76A···C57vi2.6900
H15A···H52A2.3800H76A···C58vi2.8300
H15B···H18A2.3000H76A···H58Avi2.4700
H15B···H39Cix2.6000H76A···H58Bvi2.5000
H15B···H52A2.5400H76B···C64iii3.0700
H15B···C182.8700H76B···H64Aiii2.4500
H15B···C39ix3.0200H76B···H22Bxiii2.3300
H16A···H36Aviii2.3600H78A···C682.8700
H16B···O11i2.7800H78A···C712.7900
H18A···O6viii2.7900H78A···H27A2.5600
H18A···C162.9200H78A···H682.3100
H18A···H15B2.3000H78A···H71A2.2700
H18A···C152.7300H78B···O2iii2.6300
H18B···C82.8100H78B···H72B2.5000
H18B···H82.2300H78C···C752.6600
H18B···H11B2.2300H78C···C762.8700
H18B···C112.7600H78C···H35A2.5000
H18C···H12B2.4900H78C···H75B2.2200
H19A···C45v2.9900H79A···O16i2.8400
H19A···C46v3.0000H79A···C622.8000
H19A···H4B2.2300H79A···C642.7400
H19A···C22.8900H79A···H62A2.2600
H19A···C42.7400H79A···H64A2.2500
H19A···H2A2.3800H79B···C712.6800
H19B···H1A2.3800H79B···H9iii2.5100
H19B···H11B2.2300H79B···H61A2.4600
H19B···C112.7100H79B···H71A2.1800
H19C···H82.3600H79C···C682.9200
H19C···H11B2.4900H79C···C713.0900
H19C···C44v2.9300H79C···H262.4500
H19C···H44Av2.4400H79C···H682.3700
H19C···C82.9100H79C···H71A2.5700
C3—O1—C20114.8 (2)H39A—C39—H39B109.00
C23—O5—C40117.9 (2)C30—C39—H39A109.00
C43—O11—C60116.38 (19)C42—C41—C50114.5 (2)
C63—O15—C80116.24 (18)C41—C42—C43109.3 (2)
C2—C1—C10114.3 (2)O11—C43—C42107.14 (19)
C1—C2—C3109.1 (2)O11—C43—C44107.9 (2)
O1—C3—C4106.99 (19)C42—C43—C44111.6 (2)
O1—C3—C2111.2 (2)C43—C44—C45111.5 (2)
C2—C3—C4111.0 (2)C44—C45—C46119.8 (2)
C3—C4—C5110.39 (19)C44—C45—C50116.1 (2)
C4—C5—C10116.5 (2)C46—C45—C50124.2 (2)
C4—C5—C6119.7 (2)C45—C46—C47124.5 (2)
C6—C5—C10123.8 (2)C46—C47—C48111.7 (2)
C5—C6—C7124.2 (2)C47—C48—C49109.6 (2)
C6—C7—C8113.4 (2)C47—C48—C54110.6 (2)
C9—C8—C14107.77 (19)C49—C48—C54109.4 (2)
C7—C8—C14110.7 (2)C48—C49—C50112.3 (2)
C7—C8—C9111.1 (2)C48—C49—C51112.8 (2)
C8—C9—C11111.21 (19)C50—C49—C51112.5 (2)
C8—C9—C10112.79 (19)C41—C50—C45108.0 (2)
C10—C9—C11112.6 (2)C41—C50—C49109.2 (2)
C1—C10—C9109.0 (2)C41—C50—C59109.9 (2)
C1—C10—C5107.75 (19)C45—C50—C49109.7 (2)
C5—C10—C19108.8 (2)C45—C50—C59108.6 (2)
C9—C10—C19111.2 (2)C49—C50—C59111.46 (19)
C1—C10—C19109.4 (2)C49—C51—C52114.9 (2)
C5—C10—C9110.7 (2)C51—C52—C53109.9 (2)
C9—C11—C12113.8 (3)C52—C53—C54109.1 (2)
C11—C12—C13109.5 (2)C52—C53—C57115.8 (2)
C12—C13—C14108.1 (2)C52—C53—C58111.8 (2)
C14—C13—C17101.6 (2)C54—C53—C57100.0 (2)
C14—C13—C18113.5 (2)C54—C53—C58113.0 (2)
C17—C13—C18104.2 (2)C57—C53—C58106.8 (2)
C12—C13—C18111.7 (2)C48—C54—C53113.5 (2)
C12—C13—C17117.5 (2)C48—C54—C55119.8 (2)
C8—C14—C15120.5 (2)C53—C54—C55104.8 (2)
C8—C14—C13113.9 (2)C54—C55—C56102.6 (2)
C13—C14—C15104.6 (2)C55—C56—C57105.9 (2)
C14—C15—C16102.1 (2)O13—C57—C53126.3 (3)
C15—C16—C17105.9 (2)O13—C57—C56125.6 (2)
C13—C17—C16108.4 (2)C53—C57—C56108.0 (2)
O3—C17—C13126.2 (3)O11—C60—O12126.2 (2)
O3—C17—C16125.3 (3)O11—C60—C80109.8 (2)
O1—C20—O2125.9 (2)O12—C60—C80124.0 (2)
O1—C20—C40112.2 (2)C62—C61—C70113.5 (2)
O2—C20—C40121.9 (2)C61—C62—C63109.3 (2)
C22—C21—C30113.8 (2)O15—C63—C62108.8 (2)
C21—C22—C23108.6 (2)O15—C63—C64105.82 (18)
C22—C23—C24111.7 (2)C62—C63—C64110.9 (2)
O5—C23—C24104.6 (2)C63—C64—C65112.6 (2)
O5—C23—C22111.6 (2)C64—C65—C66121.1 (2)
C23—C24—C25111.9 (2)C64—C65—C70115.7 (2)
C26—C25—C30123.1 (2)C66—C65—C70123.2 (2)
C24—C25—C26120.2 (2)C65—C66—C67124.7 (2)
C24—C25—C30116.6 (2)C66—C67—C68113.8 (2)
C25—C26—C27125.1 (2)C67—C68—C69110.6 (2)
C26—C27—C28112.8 (2)C67—C68—C74111.1 (2)
C27—C28—C34109.8 (2)C69—C68—C74107.2 (2)
C27—C28—C29109.7 (2)C68—C69—C70112.9 (2)
C29—C28—C34109.3 (2)C68—C69—C71112.1 (2)
C28—C29—C31112.5 (2)C70—C69—C71112.4 (2)
C28—C29—C30112.4 (2)C61—C70—C65107.6 (2)
C30—C29—C31113.6 (2)C61—C70—C69108.09 (19)
C21—C30—C39109.7 (2)C61—C70—C79110.7 (2)
C25—C30—C29109.94 (19)C65—C70—C69111.0 (2)
C25—C30—C39109.3 (2)C65—C70—C79108.4 (2)
C29—C30—C39111.39 (19)C69—C70—C79111.1 (2)
C21—C30—C25107.6 (2)C69—C71—C72113.9 (3)
C21—C30—C29108.9 (2)C71—C72—C73109.7 (3)
C29—C31—C32113.2 (2)C72—C73—C74109.6 (2)
C31—C32—C33109.6 (2)C72—C73—C77116.2 (2)
C32—C33—C38112.4 (2)C72—C73—C78112.2 (3)
C34—C33—C3799.6 (2)C74—C73—C77101.0 (2)
C34—C33—C38114.3 (2)C74—C73—C78113.6 (2)
C37—C33—C38105.9 (2)C77—C73—C78103.7 (2)
C32—C33—C34108.6 (2)C68—C74—C73113.5 (2)
C32—C33—C37115.5 (2)C68—C74—C75120.8 (2)
C28—C34—C33114.8 (2)C73—C74—C75104.5 (2)
C33—C34—C35104.8 (2)C74—C75—C76101.3 (2)
C28—C34—C35120.7 (2)C75—C76—C77106.1 (3)
C34—C35—C36101.3 (2)O16—C77—C73126.4 (3)
C35—C36—C37106.0 (2)O16—C77—C76125.0 (3)
O6—C37—C33126.9 (3)C73—C77—C76108.6 (3)
O6—C37—C36125.1 (2)O14—C80—O15127.2 (2)
C33—C37—C36108.0 (2)O14—C80—C60121.8 (2)
O4—C40—O5127.6 (2)O15—C80—C60111.0 (2)
O5—C40—C20107.9 (2)C42—C41—H41A109.00
O4—C40—C20124.5 (2)C42—C41—H41B109.00
C2—C1—H1B109.00C50—C41—H41A109.00
C2—C1—H1A109.00C50—C41—H41B109.00
H1A—C1—H1B108.00H41A—C41—H41B108.00
C10—C1—H1A109.00C41—C42—H42A110.00
C10—C1—H1B109.00C41—C42—H42B110.00
C3—C2—H2A110.00C43—C42—H42A110.00
C3—C2—H2B110.00C43—C42—H42B110.00
H2A—C2—H2B108.00H42A—C42—H42B108.00
C1—C2—H2B110.00O11—C43—H43110.00
C1—C2—H2A110.00C42—C43—H43110.00
C2—C3—H3109.00C44—C43—H43110.00
C4—C3—H3109.00C43—C44—H44A109.00
O1—C3—H3109.00C43—C44—H44B109.00
C5—C4—H4A110.00C45—C44—H44A109.00
C3—C4—H4A110.00C45—C44—H44B109.00
C3—C4—H4B110.00H44A—C44—H44B108.00
H4A—C4—H4B108.00C45—C46—H46118.00
C5—C4—H4B110.00C47—C46—H46118.00
C7—C6—H6118.00C46—C47—H47A109.00
C5—C6—H6118.00C46—C47—H47B109.00
C8—C7—H7A109.00C48—C47—H47A109.00
C6—C7—H7A109.00C48—C47—H47B109.00
C6—C7—H7B109.00H47A—C47—H47B108.00
H7A—C7—H7B108.00C47—C48—H48109.00
C8—C7—H7B109.00C49—C48—H48109.00
C9—C8—H8109.00C54—C48—H48109.00
C14—C8—H8109.00C48—C49—H49106.00
C7—C8—H8109.00C50—C49—H49106.00
C11—C9—H9107.00C51—C49—H49106.00
C8—C9—H9107.00C49—C51—H51A109.00
C10—C9—H9107.00C49—C51—H51B109.00
C12—C11—H11A109.00C52—C51—H51A109.00
C12—C11—H11B109.00C52—C51—H51B109.00
H11A—C11—H11B108.00H51A—C51—H51B108.00
C9—C11—H11B109.00C51—C52—H52A110.00
C9—C11—H11A109.00C51—C52—H52B110.00
C11—C12—H12B110.00C53—C52—H52A110.00
C11—C12—H12A110.00C53—C52—H52B110.00
H12A—C12—H12B108.00H52A—C52—H52B108.00
C13—C12—H12B110.00C48—C54—H54106.00
C13—C12—H12A110.00C53—C54—H54106.00
C13—C14—H14106.00C55—C54—H54106.00
C15—C14—H14106.00C54—C55—H55A111.00
C8—C14—H14106.00C54—C55—H55B111.00
C16—C15—H15A111.00C56—C55—H55A111.00
C14—C15—H15A111.00C56—C55—H55B111.00
C14—C15—H15B111.00H55A—C55—H55B109.00
H15A—C15—H15B109.00C55—C56—H56A111.00
C16—C15—H15B111.00C55—C56—H56B111.00
C15—C16—H16B111.00C57—C56—H56A111.00
C15—C16—H16A111.00C57—C56—H56B111.00
H16A—C16—H16B109.00H56A—C56—H56B109.00
C17—C16—H16A111.00C53—C58—H58A109.00
C17—C16—H16B111.00C53—C58—H58B109.00
C13—C18—H18C110.00C53—C58—H58C109.00
H18A—C18—H18B109.00H58A—C58—H58B109.00
H18A—C18—H18C109.00H58A—C58—H58C109.00
H18B—C18—H18C109.00H58B—C58—H58C109.00
C13—C18—H18B109.00C50—C59—H59A109.00
C13—C18—H18A109.00C50—C59—H59B109.00
C10—C19—H19B109.00C50—C59—H59C109.00
C10—C19—H19A110.00H59A—C59—H59B110.00
H19A—C19—H19C109.00H59A—C59—H59C109.00
H19B—C19—H19C109.00H59B—C59—H59C109.00
C10—C19—H19C109.00C62—C61—H61A109.00
H19A—C19—H19B109.00C62—C61—H61B109.00
C30—C21—H21A109.00C70—C61—H61A109.00
C22—C21—H21A109.00C70—C61—H61B109.00
C22—C21—H21B109.00H61A—C61—H61B108.00
H21A—C21—H21B108.00C61—C62—H62A110.00
C30—C21—H21B109.00C61—C62—H62B110.00
C23—C22—H22A110.00C63—C62—H62A110.00
C23—C22—H22B110.00C63—C62—H62B110.00
H22A—C22—H22B108.00H62A—C62—H62B108.00
C21—C22—H22B110.00O15—C63—H63110.00
C21—C22—H22A110.00C62—C63—H63110.00
C24—C23—H23110.00C64—C63—H63110.00
O5—C23—H23110.00C63—C64—H64A109.00
C22—C23—H23110.00C63—C64—H64B109.00
C25—C24—H24A109.00C65—C64—H64A109.00
C25—C24—H24B109.00C65—C64—H64B109.00
H24A—C24—H24B108.00H64A—C64—H64B108.00
C23—C24—H24B109.00C65—C66—H66118.00
C23—C24—H24A109.00C67—C66—H66118.00
C27—C26—H26117.00C66—C67—H67A109.00
C25—C26—H26117.00C66—C67—H67B109.00
C28—C27—H27A109.00C68—C67—H67A109.00
C28—C27—H27B109.00C68—C67—H67B109.00
H27A—C27—H27B108.00H67A—C67—H67B108.00
C26—C27—H27A109.00C67—C68—H68109.00
C26—C27—H27B109.00C69—C68—H68109.00
C34—C28—H28109.00C74—C68—H68109.00
C27—C28—H28109.00C68—C69—H69106.00
C29—C28—H28109.00C70—C69—H69106.00
C31—C29—H29106.00C71—C69—H69106.00
C28—C29—H29106.00C69—C71—H71A109.00
C30—C29—H29106.00C69—C71—H71B109.00
C29—C31—H31A109.00C72—C71—H71A109.00
C32—C31—H31B109.00C72—C71—H71B109.00
C29—C31—H31B109.00H71A—C71—H71B108.00
C32—C31—H31A109.00C71—C72—H72A110.00
H31A—C31—H31B108.00C71—C72—H72B110.00
C33—C32—H32A110.00C73—C72—H72A110.00
C33—C32—H32B110.00C73—C72—H72B110.00
H32A—C32—H32B108.00H72A—C72—H72B108.00
C31—C32—H32B110.00C68—C74—H74106.00
C31—C32—H32A110.00C73—C74—H74106.00
C35—C34—H34105.00C75—C74—H74106.00
C28—C34—H34105.00C74—C75—H75A112.00
C33—C34—H34105.00C74—C75—H75B112.00
C36—C35—H35A112.00C76—C75—H75A112.00
C36—C35—H35B111.00C76—C75—H75B111.00
H35A—C35—H35B109.00H75A—C75—H75B109.00
C34—C35—H35B111.00C75—C76—H76A111.00
C34—C35—H35A112.00C75—C76—H76B111.00
C35—C36—H36B111.00C77—C76—H76A111.00
C35—C36—H36A111.00C77—C76—H76B110.00
H36A—C36—H36B109.00H76A—C76—H76B109.00
C37—C36—H36B111.00C73—C78—H78A109.00
C37—C36—H36A111.00C73—C78—H78B109.00
C33—C38—H38B109.00C73—C78—H78C109.00
C33—C38—H38A109.00H78A—C78—H78B109.00
H38A—C38—H38C109.00H78A—C78—H78C109.00
C33—C38—H38C109.00H78B—C78—H78C110.00
H38A—C38—H38B109.00C70—C79—H79A109.00
H38B—C38—H38C109.00C70—C79—H79B109.00
C30—C39—H39B109.00C70—C79—H79C109.00
C30—C39—H39C109.00H79A—C79—H79B109.00
H39A—C39—H39C109.00H79A—C79—H79C110.00
H39B—C39—H39C109.00H79B—C79—H79C109.00
C20—O1—C3—C284.0 (3)C37—C33—C34—C28179.0 (2)
C20—O1—C3—C4−154.6 (2)C37—C33—C34—C3544.2 (2)
C3—O1—C20—O2−5.2 (4)C34—C33—C37—C36−29.3 (3)
C3—O1—C20—C40174.0 (2)C28—C34—C35—C36−173.7 (2)
C40—O5—C23—C2279.6 (3)C33—C34—C35—C36−42.2 (2)
C40—O5—C23—C24−159.6 (2)C34—C35—C36—C3722.6 (3)
C23—O5—C40—O4−3.7 (4)C35—C36—C37—O6−174.2 (3)
C23—O5—C40—C20176.8 (2)C35—C36—C37—C334.3 (3)
C43—O11—C60—C80171.9 (2)C50—C41—C42—C43−57.1 (3)
C60—O11—C43—C42163.3 (2)C42—C41—C50—C4551.4 (3)
C60—O11—C43—C44−76.5 (3)C42—C41—C50—C49170.6 (2)
C43—O11—C60—O12−7.0 (4)C42—C41—C50—C59−66.9 (3)
C63—O15—C80—O148.5 (4)C41—C42—C43—O11175.0 (2)
C80—O15—C63—C64−169.5 (2)C41—C42—C43—C4457.1 (3)
C63—O15—C80—C60−172.3 (2)O11—C43—C44—C45−172.52 (19)
C80—O15—C63—C6271.3 (3)C42—C43—C44—C45−55.1 (3)
C2—C1—C10—C19−67.9 (3)C43—C44—C45—C46−127.7 (3)
C2—C1—C10—C9170.4 (2)C43—C44—C45—C5052.2 (3)
C2—C1—C10—C550.2 (3)C44—C45—C46—C47−178.5 (2)
C10—C1—C2—C3−57.4 (3)C50—C45—C46—C471.6 (4)
C1—C2—C3—C459.5 (3)C44—C45—C50—C41−48.9 (3)
C1—C2—C3—O1178.4 (2)C44—C45—C50—C49−167.8 (2)
O1—C3—C4—C5−178.8 (2)C44—C45—C50—C5970.2 (3)
C2—C3—C4—C5−57.4 (3)C46—C45—C50—C41131.0 (3)
C3—C4—C5—C1053.5 (3)C46—C45—C50—C4912.2 (3)
C3—C4—C5—C6−125.6 (3)C46—C45—C50—C59−109.9 (3)
C4—C5—C6—C7−177.2 (2)C45—C46—C47—C4815.9 (4)
C10—C5—C6—C73.9 (4)C46—C47—C48—C49−46.0 (3)
C4—C5—C10—C1−48.5 (3)C46—C47—C48—C54−166.6 (2)
C4—C5—C10—C9−167.6 (2)C47—C48—C49—C5061.9 (3)
C4—C5—C10—C1970.0 (3)C47—C48—C49—C51−169.67 (19)
C6—C5—C10—C1130.5 (3)C54—C48—C49—C50−176.7 (2)
C6—C5—C10—C911.4 (4)C54—C48—C49—C51−48.3 (3)
C6—C5—C10—C19−111.0 (3)C47—C48—C54—C53178.2 (2)
C5—C6—C7—C811.7 (4)C47—C48—C54—C55−57.2 (3)
C6—C7—C8—C14−161.2 (2)C49—C48—C54—C5357.4 (3)
C6—C7—C8—C9−41.5 (3)C49—C48—C54—C55−178.0 (2)
C7—C8—C9—C1057.9 (3)C48—C49—C50—C41−161.6 (2)
C7—C8—C9—C11−174.5 (2)C48—C49—C50—C45−43.4 (3)
C14—C8—C9—C11−53.0 (3)C48—C49—C50—C5976.9 (3)
C7—C8—C14—C13−178.1 (2)C51—C49—C50—C4169.9 (3)
C14—C8—C9—C10179.4 (2)C51—C49—C50—C45−172.0 (2)
C9—C8—C14—C15−174.2 (2)C51—C49—C50—C59−51.6 (3)
C7—C8—C14—C15−52.5 (3)C48—C49—C51—C5247.5 (3)
C9—C8—C14—C1360.2 (3)C50—C49—C51—C52175.8 (2)
C11—C9—C10—C19−47.5 (3)C49—C51—C52—C53−51.4 (3)
C8—C9—C10—C1−160.0 (2)C51—C52—C53—C5456.7 (3)
C8—C9—C10—C5−41.7 (3)C51—C52—C53—C57168.5 (2)
C8—C9—C10—C1979.4 (3)C51—C52—C53—C58−68.9 (3)
C11—C9—C10—C173.1 (3)C52—C53—C54—C48−62.7 (3)
C8—C9—C11—C1253.0 (3)C52—C53—C54—C55164.8 (2)
C10—C9—C11—C12−179.3 (2)C57—C53—C54—C48175.4 (2)
C11—C9—C10—C5−168.6 (2)C57—C53—C54—C5543.0 (3)
C9—C11—C12—C13−54.4 (3)C58—C53—C54—C4862.3 (3)
C11—C12—C13—C1456.5 (3)C58—C53—C54—C55−70.2 (2)
C11—C12—C13—C18−69.1 (3)C52—C53—C57—O1330.5 (4)
C11—C12—C13—C17170.6 (2)C52—C53—C57—C56−147.6 (2)
C12—C13—C14—C8−62.7 (3)C54—C53—C57—O13147.4 (3)
C14—C13—C17—C16−22.9 (3)C54—C53—C57—C56−30.6 (3)
C18—C13—C17—O3−82.3 (3)C58—C53—C57—O13−94.8 (3)
C18—C13—C17—C1695.3 (3)C58—C53—C57—C5687.2 (3)
C18—C13—C14—C861.8 (3)C48—C54—C55—C56−168.0 (2)
C18—C13—C14—C15−71.8 (3)C53—C54—C55—C56−39.3 (2)
C12—C13—C17—O341.8 (4)C54—C55—C56—C5719.2 (3)
C12—C13—C17—C16−140.6 (2)C55—C56—C57—O13−170.7 (3)
C12—C13—C14—C15163.7 (2)C55—C56—C57—C537.4 (3)
C17—C13—C14—C8173.0 (2)O11—C60—C80—O14−51.6 (4)
C17—C13—C14—C1539.4 (3)O11—C60—C80—O15129.1 (2)
C14—C13—C17—O3159.5 (3)O12—C60—C80—O14127.3 (3)
C8—C14—C15—C16−170.7 (2)O12—C60—C80—O15−52.0 (4)
C13—C14—C15—C16−40.9 (3)C70—C61—C62—C63−60.9 (3)
C14—C15—C16—C1725.8 (3)C62—C61—C70—C6554.9 (3)
C15—C16—C17—O3175.8 (3)C62—C61—C70—C69174.8 (2)
C15—C16—C17—C13−1.8 (3)C62—C61—C70—C79−63.3 (3)
O1—C20—C40—O424.8 (4)C61—C62—C63—O15173.5 (2)
O1—C20—C40—O5−155.7 (2)C61—C62—C63—C6457.5 (3)
O2—C20—C40—O523.5 (4)O15—C63—C64—C65−170.4 (2)
O2—C20—C40—O4−156.0 (3)C62—C63—C64—C65−52.6 (3)
C22—C21—C30—C29172.4 (2)C63—C64—C65—C66−131.3 (3)
C22—C21—C30—C39−65.5 (3)C63—C64—C65—C7050.0 (3)
C30—C21—C22—C23−60.4 (3)C64—C65—C66—C67−178.6 (2)
C22—C21—C30—C2553.3 (3)C70—C65—C66—C670.0 (4)
C21—C22—C23—C2458.6 (3)C64—C65—C70—C61−49.2 (3)
C21—C22—C23—O5175.2 (2)C64—C65—C70—C69−167.2 (2)
C22—C23—C24—C25−53.5 (3)C64—C65—C70—C7970.5 (3)
O5—C23—C24—C25−174.3 (2)C66—C65—C70—C61132.1 (3)
C23—C24—C25—C26−131.4 (3)C66—C65—C70—C6914.1 (4)
C23—C24—C25—C3049.0 (3)C66—C65—C70—C79−108.1 (3)
C24—C25—C26—C27−177.9 (2)C65—C66—C67—C6814.4 (4)
C30—C25—C26—C271.6 (4)C66—C67—C68—C69−41.7 (3)
C24—C25—C30—C21−47.5 (3)C66—C67—C68—C74−160.6 (2)
C24—C25—C30—C29−166.0 (2)C67—C68—C69—C7057.0 (3)
C24—C25—C30—C3971.5 (3)C67—C68—C69—C71−174.8 (2)
C26—C25—C30—C21132.9 (3)C74—C68—C69—C70178.3 (2)
C26—C25—C30—C2914.5 (4)C74—C68—C69—C71−53.6 (3)
C26—C25—C30—C39−108.1 (3)C67—C68—C74—C73−179.6 (2)
C25—C26—C27—C2813.1 (4)C67—C68—C74—C75−54.3 (3)
C26—C27—C28—C34−162.8 (2)C69—C68—C74—C7359.5 (3)
C26—C27—C28—C29−42.7 (3)C69—C68—C74—C75−175.3 (2)
C27—C28—C29—C31−169.71 (19)C68—C69—C70—C61−160.0 (2)
C34—C28—C29—C30−179.0 (2)C68—C69—C70—C65−42.3 (3)
C27—C28—C29—C3060.6 (3)C68—C69—C70—C7978.4 (3)
C27—C28—C34—C33175.2 (2)C71—C69—C70—C6171.9 (3)
C27—C28—C34—C35−57.8 (3)C71—C69—C70—C65−170.4 (2)
C34—C28—C29—C31−49.3 (3)C71—C69—C70—C79−49.7 (3)
C29—C28—C34—C3354.8 (3)C68—C69—C71—C7252.8 (4)
C29—C28—C34—C35−178.1 (2)C70—C69—C71—C72−178.8 (3)
C28—C29—C31—C3252.3 (3)C69—C71—C72—C73−52.7 (4)
C28—C29—C30—C21−162.9 (2)C71—C72—C73—C7455.1 (3)
C28—C29—C30—C25−45.2 (3)C71—C72—C73—C77168.8 (3)
C28—C29—C30—C3976.1 (3)C71—C72—C73—C78−72.1 (3)
C31—C29—C30—C2168.0 (3)C72—C73—C74—C68−62.0 (3)
C31—C29—C30—C25−174.3 (2)C72—C73—C74—C75164.4 (2)
C30—C29—C31—C32−178.6 (2)C77—C73—C74—C68174.8 (2)
C31—C29—C30—C39−53.0 (3)C77—C73—C74—C7541.3 (2)
C29—C31—C32—C33−56.2 (3)C78—C73—C74—C6864.4 (3)
C31—C32—C33—C3457.6 (3)C78—C73—C74—C75−69.1 (3)
C31—C32—C33—C37168.4 (2)C72—C73—C77—O1636.4 (4)
C31—C32—C33—C38−69.9 (3)C72—C73—C77—C76−143.6 (3)
C32—C33—C34—C28−59.8 (3)C74—C73—C77—O16154.9 (3)
C32—C33—C34—C35165.40 (19)C74—C73—C77—C76−25.1 (3)
C38—C33—C37—O6−92.0 (3)C78—C73—C77—O16−87.3 (4)
C38—C33—C37—C3689.6 (3)C78—C73—C77—C7692.8 (3)
C38—C33—C34—C2866.6 (3)C68—C74—C75—C76−170.7 (3)
C38—C33—C34—C35−68.2 (3)C73—C74—C75—C76−41.4 (3)
C32—C33—C37—O633.2 (4)C74—C75—C76—C7725.0 (3)
C32—C33—C37—C36−145.3 (2)C75—C76—C77—O16−180.0 (3)
C34—C33—C37—O6149.2 (3)C75—C76—C77—C730.0 (3)
Symmetry codes: (i) x+1, y, z; (ii) −x, y+1/2, −z+1; (iii) x−1, y, z; (iv) x+2, y, z; (v) −x+1, y−1/2, −z; (vi) x−2, y, z+1; (vii) −x−1, y−1/2, −z+1; (viii) x+2, y, z−1; (ix) x+1, y, z−1; (x) −x, y−1/2, −z+1; (xi) x−1, y, z+1; (xii) −x+1, y+1/2, −z; (xiii) −x−1, y+1/2, −z+1; (xiv) x−2, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4A···O3iii0.99002.55003.526 (3)171.00
C21—H21A···O12x0.99002.36003.349 (3)173.00
C34—H34···O2iii1.00002.32003.239 (3)152.00
C47—H47A···O14i0.99002.54003.439 (3)151.00
C62—H62B···O140.99002.56003.095 (3)114.00
C64—H64A···O16i0.99002.57003.484 (4)154.00
Symmetry codes: (i) x+1, y, z; (iii) x−1, y, z; (x) −x, y−1/2, −z+1.

Experimental details

Crystal data
Chemical formulaC40H54O6
Mr630.83
Crystal system, space groupMonoclinic, P21
Temperature (K)120
a, b, c (Å)10.9843 (2), 22.8189 (4), 13.5307 (3)
β (°) 90.4679 (8)
V (Å3)3391.35 (11)
Z4
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.4 × 0.18 × 0.12
Data collection
DiffractometerBruker Nonius KappaCCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.767, 0.990
No. of measured, independent and
observed [I > 2σ(I)] reflections		47104, 7977, 6961
Rint0.052
(sin θ/λ)max (Å−1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.101, 1.08
No. of reflections7977
No. of parameters837
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.24, −0.21

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998), DENZO and COLLECT, SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4A···O3i0.99002.55003.526 (3)171.00
C21—H21A···O12ii0.99002.36003.349 (3)173.00
C34—H34···O2i1.00002.32003.239 (3)152.00
C47—H47A···O14iii0.99002.54003.439 (3)151.00
C62—H62B···O140.99002.56003.095 (3)114.00
C64—H64A···O16iii0.99002.57003.484 (4)154.00
Symmetry codes: (i) x−1, y, z; (ii) −x, y−1/2, −z+1; (iii) x+1, y, z.
 

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