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Naltrexone [systematic name: (4R,4aS,7aR,12bS)-3-cyclo­propyl­methyl-4a,9-di­hy­droxy-2,4,5,6,7a,13-hexa­hydro-1H-4,12-methano­benzofuro[3,2-e]iso­quino­lin-7-one] is an important morphine-related drug used for combating alcoholism and opioid dependence. Of the eight crystal forms of naltrexone known thus far, only one exists in the neutral form and it crystallizes as a monohydrate. We have isolated the naltrexone free base as two new solvate forms, i.e. the ethyl acetate 0.33-solvate, C20H23NO4·0.33C4H8O2, (I), and the diethyl ether hemisolvate, C20H23NO4·0.5C4H10O, (II). While just one solvent mol­ecule is present in the asymmetric unit of each solvate, there are three drug mol­ecules (Z′ = 3) in ethyl acetate solvate (I) and two (Z′ = 2) in diethyl ether solvate (II). In (I), one of the three crystallographically independent drug mol­ecules is present with its cyclo­propyl group disordered over two sets of positions, as is the whole diethyl ether solvent mol­ecule in (II). In all known forms, including the title forms, the naltrexone molecule exhibits the same conformation of the fused rings. The only conformational variability of naltrexone is in the cyclo­propyl­methyl group. Two conformations can be found around the bond connecting this group to the N-heterocycle, which is directly related to drug protonation. We have calculated, at the B3LYP/6-31G** level of theory, the minimum energy conformations of protonated and neutral naltrexone mol­ecules for a chosen torsion angle about this bond. The lowest energy conformers depend on the protonation state and are in agreement with those found in the solid state. Within the cyclopropylmethyl group, the bond joining the methylene C atom to the cyclopropyl fragment also evidences conformational variability. In the literature, there are two well defined conformations around this bond. A third cyclo­propyl conformation around this second bond is observed in the title solvates. Concerning the supra­molecular features of the previously reported crystal structures, only one classical hydrogen bond between naltrexone mol­ecules and one C(8) homosynthon is known, pointing to the robustness of this synthon and the difficulty in disrupting it. New R22(7) and C22(10) homo­synthons are found in both (I) and (II), suggesting that their occurrence derives from crystallization of the neutral drug from nonpolar solvents.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618001791/cu3125sup1.cif
Contains datablocks global, naltrexone_AcOEt, naltrexone_Et2O

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618001791/cu3125naltrexone_AcOEtsup2.hkl
Contains datablock naltrexone_AcOEt

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618001791/cu3125naltrexone_Et2Osup3.hkl
Contains datablock naltrexone_Et2O

CCDC references: 1820437; 1820436

Computing details top

For both structures, data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012).

(4R,4aS,7aR,12bS)-3-Cyclopropylmethyl-4a,9-dihydroxy-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one ethyl acetate 0.33-solvate (naltrexone_AcOEt) top
Crystal data top
3C20H23NO4·C4H8O2Dx = 1.282 Mg m3
Mr = 1112.29Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, P212121Cell parameters from 2253 reflections
a = 13.0034 (4) Åθ = 4.2–52.1°
b = 14.0829 (4) ŵ = 0.73 mm1
c = 31.479 (1) ÅT = 296 K
V = 5764.6 (3) Å3Prism, colourless
Z = 40.22 × 0.18 × 0.10 mm
F(000) = 2376
Data collection top
Bruker APEXII CCD
diffractometer
7082 reflections with I > 2σ(I)
CCD scansRint = 0.034
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
θmax = 66.6°, θmin = 2.8°
Tmin = 0.793, Tmax = 0.929h = 1515
20908 measured reflectionsk = 1613
9344 independent reflectionsl = 3632
Refinement top
Refinement on F2Hydrogen site location: constr
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.052 w = 1/[σ2(Fo2) + (0.0843P)2 + 0.2244P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.146(Δ/σ)max < 0.001
S = 1.01Δρmax = 0.30 e Å3
9344 reflectionsΔρmin = 0.23 e Å3
756 parametersAbsolute structure: Flack x determined using 2489 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraintAbsolute structure parameter: 0.00 (12)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C19B0.2678 (6)0.1762 (8)0.8426 (3)0.142 (3)
H19A0.2810.21170.81670.17*0.737 (19)
H19B0.22750.11880.83880.17*0.737 (19)
H19'0.19860.1950.83470.17*0.264 (19)
H19"0.31160.15640.81920.17*0.264 (19)
O1A0.2025 (2)0.7568 (3)0.93957 (12)0.0812 (11)
H1OA0.18950.7160.95740.122*
O2A0.0051 (2)0.7342 (2)0.98561 (10)0.0608 (8)
O4A0.3103 (2)0.8762 (2)0.99844 (9)0.0553 (7)
H4OA0.34860.84620.98270.083*
O3A0.0254 (3)0.8428 (3)1.05550 (13)0.0871 (11)
O1C0.6456 (3)0.4318 (3)0.76068 (15)0.0893 (12)
H1OC0.58690.42460.76960.134*
O2C0.5389 (2)0.2450 (2)0.76809 (10)0.0683 (8)
O3C0.3814 (3)0.2488 (4)0.71285 (15)0.1202 (17)
O4C0.5455 (3)0.0538 (2)0.70877 (12)0.0725 (9)
H4OC0.58390.09020.72150.109*
O1B1.0266 (2)0.1769 (3)0.94123 (12)0.0721 (9)
H1OB1.01890.16730.96670.108*
O2B0.8399 (2)0.2305 (2)0.99131 (9)0.0574 (7)
O4B0.5216 (2)0.3676 (2)0.97445 (11)0.0615 (8)
H4OB0.47760.32990.96640.092*
C13A0.1511 (3)0.8133 (2)0.96721 (13)0.0433 (8)
N1A0.3210 (3)0.8650 (3)0.91451 (11)0.0549 (9)
O3B0.8752 (3)0.4114 (3)1.01275 (15)0.0932 (12)
C3B0.9370 (3)0.2094 (3)0.92437 (15)0.0544 (10)
C4B0.8505 (3)0.2325 (3)0.94734 (14)0.0520 (10)
O2S0.9737 (5)0.5073 (5)0.8661 (2)0.154 (2)
C3A0.1145 (3)0.8063 (4)0.93004 (15)0.0607 (11)
C4A0.0226 (3)0.7927 (3)0.95091 (14)0.0526 (10)
C12A0.0630 (3)0.8430 (3)0.93933 (13)0.0485 (9)
C15A0.2167 (3)0.7368 (3)0.94539 (14)0.0512 (9)
H15A0.17350.68330.93770.061*
H15B0.2690.71430.9650.061*
C16A0.2678 (3)0.7760 (3)0.90588 (14)0.0575 (11)
H16A0.21610.78640.88420.069*
H16B0.31670.72990.89510.069*
C17A0.3821 (4)0.8986 (4)0.87857 (16)0.0725 (14)
H17A0.34660.88330.85240.087*
H17B0.38830.96720.88020.087*
C18A0.4869 (5)0.8560 (6)0.8775 (2)0.099 (2)
H18A0.48960.78690.8740.118*
C20A0.5681 (5)0.8971 (5)0.9023 (2)0.0923 (18)
H20A0.55140.95190.91970.111*
H20B0.61830.85430.91470.111*
C5A0.0878 (3)0.7736 (3)1.00491 (13)0.0498 (10)
H5A0.12650.72311.01910.06*
C19A0.5703 (4)0.9101 (6)0.8565 (2)0.100 (2)
H19C0.55410.97250.84540.12*
H19D0.62110.87480.84040.12*
C9A0.2510 (3)0.9383 (3)0.93151 (13)0.0502 (9)
H9A0.29280.99520.93640.06*
C10A0.1607 (4)0.9689 (3)0.90250 (16)0.0626 (12)
H10A0.18220.96280.87310.075*
H10B0.14591.03540.90770.075*
C11A0.0634 (3)0.9128 (3)0.90868 (14)0.0552 (10)
C1A0.0303 (4)0.9277 (4)0.88838 (16)0.0671 (12)
H1A0.03520.97430.86750.081*
C2A0.1160 (4)0.8751 (4)0.89854 (16)0.0724 (14)
H2A0.17690.8860.88380.087*
C14A0.2181 (3)0.9013 (3)0.97572 (13)0.0474 (9)
C8A0.1625 (3)0.9739 (3)1.00238 (14)0.0561 (10)
H8A10.20771.02731.0080.067*
H8A20.10290.99730.9870.067*
C7A0.1281 (4)0.9296 (3)1.04439 (15)0.0613 (11)
H7A10.09410.97741.06160.074*
H7A20.18790.90741.05990.074*
C6A0.0567 (3)0.8489 (3)1.03714 (15)0.0583 (11)
C3C0.6808 (4)0.3474 (3)0.74384 (16)0.0666 (12)
C4C0.6321 (3)0.2625 (3)0.74720 (14)0.0584 (11)
C12C0.6687 (3)0.1829 (3)0.72790 (13)0.0546 (10)
C11C0.7550 (4)0.1825 (3)0.70277 (14)0.0616 (11)
C10C0.7785 (4)0.0947 (4)0.67797 (17)0.0753 (14)
H10C0.84990.07780.68260.09*
H10D0.770.10840.6480.09*
C9C0.7108 (4)0.0093 (4)0.68949 (15)0.0667 (13)
H9C0.70910.03170.66430.08*
N1C0.7455 (3)0.0510 (3)0.72529 (13)0.0687 (10)
C17C0.8397 (4)0.1039 (4)0.7160 (2)0.0844 (16)
H17C0.89780.06080.71730.101*
H17D0.83580.12880.68730.101*
C18C0.8575 (4)0.1833 (5)0.7458 (2)0.0902 (17)
H18C0.79870.22540.75090.108*
C5C0.5031 (3)0.1548 (3)0.75016 (15)0.0590 (11)
H5C0.46430.11960.77170.071*
C6C0.4331 (4)0.1769 (4)0.71210 (18)0.0739 (14)
C7C0.4324 (4)0.1082 (4)0.67640 (19)0.0788 (15)
H7C10.3970.13620.65230.095*
H7C20.39480.05180.68480.095*
C8C0.5409 (4)0.0804 (4)0.66312 (16)0.0722 (14)
H8C10.57790.13640.65380.087*
H8C20.53740.03650.63940.087*
C14C0.5989 (4)0.0338 (3)0.69998 (15)0.0600 (11)
C13C0.6021 (3)0.0998 (3)0.73867 (13)0.0537 (10)
C15C0.6466 (4)0.0453 (4)0.77683 (15)0.0645 (12)
H15C0.65530.08840.80060.077*
H15D0.5990.00420.78530.077*
C16C0.7497 (4)0.0012 (4)0.76547 (15)0.0716 (13)
H16C0.80110.05090.76330.086*
H16D0.77060.04170.7880.086*
C1C0.8063 (4)0.2696 (4)0.69948 (17)0.0728 (14)
H1C0.86540.27370.6830.087*
C2C0.7713 (4)0.3484 (4)0.72000 (18)0.0749 (14)
H2C0.80870.40450.71810.09*
O1S0.8152 (6)0.5506 (6)0.8733 (3)0.195 (3)
C3S0.8890 (7)0.5358 (7)0.8508 (4)0.134 (3)
C12B0.7620 (3)0.2642 (3)0.92768 (13)0.0501 (9)
C11B0.7538 (4)0.2797 (3)0.88508 (15)0.0627 (11)
C10B0.6571 (4)0.3260 (4)0.86809 (16)0.0741 (14)
H10E0.63070.28820.84470.089*
H10F0.67430.38830.8570.089*
C9B0.5720 (3)0.3368 (4)0.90204 (16)0.0645 (12)
H9B0.52880.39020.89310.077*
N1B0.5027 (3)0.2541 (3)0.90770 (12)0.0664 (10)
C17B0.4412 (4)0.2335 (6)0.86913 (18)0.097 (2)
H17E0.42040.29330.85650.116*
H17F0.48490.20110.84880.116*
C2B0.9294 (4)0.2221 (4)0.88102 (16)0.0667 (12)
H2B0.98590.20690.86430.08*
C1B0.8415 (4)0.2565 (4)0.86108 (16)0.0719 (13)
H1B0.84070.26430.83170.086*
C13B0.6788 (3)0.2771 (3)0.96057 (13)0.0486 (9)
C5B0.7505 (3)0.2913 (3)0.99952 (14)0.0528 (10)
H5B0.71550.27051.02550.063*
C6B0.7875 (4)0.3936 (3)1.00463 (16)0.0639 (12)
C7B0.7086 (4)0.4689 (3)0.9956 (2)0.0754 (15)
H7B10.73990.53130.99790.09*
H7B20.65330.46491.01620.09*
C8B0.6659 (4)0.4547 (3)0.95070 (18)0.0689 (14)
H8B10.61850.50570.9440.083*
H8B20.72180.45680.93030.083*
C14B0.6109 (3)0.3605 (3)0.94730 (15)0.0549 (11)
C16B0.5579 (4)0.1688 (3)0.92226 (15)0.0622 (11)
H16E0.60740.14970.90080.075*
H16F0.50940.11720.92610.075*
C15B0.6131 (3)0.1876 (3)0.96354 (14)0.0526 (10)
H15E0.65650.13380.97040.063*
H15F0.5630.1950.98620.063*
C18B0.3494 (9)0.1758 (11)0.8761 (3)0.096 (4)0.737 (19)
H18B0.35740.11770.89290.115*0.737 (19)
C20C0.9296 (6)0.1704 (8)0.7824 (3)0.143 (3)
H20C0.91360.20280.80880.171*
H20D0.96230.10890.78580.171*
C19C0.9607 (5)0.2300 (6)0.7450 (3)0.123 (3)
H19E1.01210.20440.72580.148*
H19F0.96340.29830.74880.148*
C20B0.2542 (11)0.2284 (13)0.8810 (3)0.132 (6)0.737 (19)
H20E0.20440.20440.90130.159*0.737 (19)
H20F0.25780.29710.87930.159*0.737 (19)
C1S1.0791 (8)0.4552 (8)0.9214 (3)0.167 (4)
H1S11.08820.45510.95160.25*
H1S21.0730.3910.91140.25*
H1S31.13740.48490.90820.25*
C2S0.9886 (11)0.5064 (9)0.9109 (3)0.189 (6)
H2S10.99430.5710.92130.227*
H2S20.92980.4770.92450.227*
C4S0.8745 (8)0.5306 (11)0.8066 (3)0.199 (6)
H4S10.93930.51860.7930.298*
H4S20.82750.480.80010.298*
H4S30.84680.58960.79650.298*
C18'0.322 (2)0.229 (2)0.8825 (9)0.072 (8)0.264 (19)
H18'0.28790.28140.89770.086*0.264 (19)
C20'0.279 (2)0.128 (2)0.8834 (8)0.091 (10)0.264 (19)
H20G0.32880.07630.88480.109*0.264 (19)
H20H0.21710.11660.89970.109*0.264 (19)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C19B0.089 (5)0.231 (10)0.106 (6)0.028 (6)0.037 (5)0.010 (7)
O1A0.0384 (16)0.123 (3)0.082 (2)0.0106 (18)0.0099 (16)0.024 (2)
O2A0.0372 (14)0.0721 (17)0.073 (2)0.0105 (13)0.0087 (14)0.0224 (16)
O4A0.0353 (14)0.0659 (17)0.0647 (18)0.0005 (12)0.0001 (13)0.0081 (15)
O3A0.066 (2)0.094 (2)0.101 (3)0.0097 (19)0.042 (2)0.013 (2)
O1C0.090 (3)0.077 (2)0.101 (3)0.014 (2)0.010 (2)0.020 (2)
O2C0.0618 (19)0.0739 (19)0.069 (2)0.0022 (16)0.0188 (16)0.0022 (17)
O3C0.102 (3)0.149 (4)0.110 (3)0.061 (3)0.002 (3)0.024 (3)
O4C0.073 (2)0.0601 (18)0.085 (2)0.0041 (16)0.0078 (19)0.0161 (17)
O1B0.0467 (17)0.084 (2)0.086 (2)0.0119 (16)0.0080 (17)0.005 (2)
O2B0.0511 (16)0.0654 (16)0.0556 (18)0.0155 (14)0.0000 (14)0.0011 (14)
O4B0.0425 (15)0.0562 (17)0.086 (2)0.0093 (12)0.0102 (16)0.0051 (16)
C13A0.0342 (19)0.0417 (18)0.054 (2)0.0012 (15)0.0007 (17)0.0013 (17)
N1A0.0459 (19)0.063 (2)0.056 (2)0.0008 (16)0.0147 (16)0.0043 (17)
O3B0.067 (2)0.091 (2)0.121 (3)0.0063 (19)0.021 (2)0.015 (2)
C3B0.043 (2)0.054 (2)0.067 (3)0.0023 (17)0.007 (2)0.004 (2)
C4B0.049 (2)0.049 (2)0.058 (3)0.0092 (18)0.003 (2)0.0006 (19)
O2S0.104 (4)0.212 (7)0.145 (6)0.007 (5)0.005 (4)0.006 (5)
C3A0.039 (2)0.084 (3)0.059 (3)0.000 (2)0.001 (2)0.003 (2)
C4A0.042 (2)0.064 (2)0.052 (2)0.0007 (18)0.0036 (19)0.004 (2)
C12A0.040 (2)0.056 (2)0.049 (2)0.0081 (17)0.0002 (18)0.0049 (19)
C15A0.043 (2)0.046 (2)0.064 (3)0.0038 (16)0.0008 (19)0.0048 (19)
C16A0.051 (2)0.059 (2)0.063 (3)0.0089 (19)0.008 (2)0.016 (2)
C17A0.058 (3)0.096 (4)0.064 (3)0.002 (3)0.018 (2)0.002 (3)
C18A0.067 (4)0.135 (5)0.094 (4)0.008 (4)0.027 (3)0.015 (4)
C20A0.081 (4)0.112 (5)0.084 (4)0.015 (3)0.000 (3)0.021 (4)
C5A0.0342 (19)0.059 (2)0.057 (2)0.0001 (17)0.0021 (18)0.012 (2)
C19A0.068 (4)0.147 (6)0.086 (4)0.006 (4)0.031 (3)0.014 (4)
C9A0.044 (2)0.049 (2)0.058 (2)0.0010 (17)0.007 (2)0.0014 (18)
C10A0.058 (3)0.060 (2)0.069 (3)0.004 (2)0.012 (2)0.015 (2)
C11A0.051 (2)0.062 (2)0.052 (2)0.0102 (19)0.005 (2)0.008 (2)
C1A0.057 (3)0.088 (3)0.056 (3)0.013 (2)0.001 (2)0.013 (2)
C2A0.051 (3)0.108 (4)0.058 (3)0.012 (3)0.011 (2)0.012 (3)
C14A0.038 (2)0.048 (2)0.056 (2)0.0027 (16)0.0030 (18)0.0032 (18)
C8A0.054 (2)0.052 (2)0.062 (3)0.0022 (19)0.007 (2)0.009 (2)
C7A0.052 (2)0.077 (3)0.055 (3)0.011 (2)0.006 (2)0.010 (2)
C6A0.043 (2)0.071 (3)0.060 (3)0.0152 (19)0.011 (2)0.017 (2)
C3C0.065 (3)0.073 (3)0.062 (3)0.007 (2)0.004 (2)0.009 (2)
C4C0.050 (2)0.075 (3)0.050 (2)0.005 (2)0.004 (2)0.002 (2)
C12C0.050 (2)0.070 (3)0.044 (2)0.007 (2)0.004 (2)0.000 (2)
C11C0.053 (3)0.079 (3)0.053 (3)0.006 (2)0.010 (2)0.003 (2)
C10C0.073 (3)0.087 (3)0.066 (3)0.002 (3)0.022 (3)0.002 (3)
C9C0.073 (3)0.078 (3)0.049 (3)0.001 (2)0.012 (2)0.003 (2)
N1C0.062 (2)0.078 (2)0.066 (2)0.012 (2)0.011 (2)0.005 (2)
C17C0.071 (3)0.087 (3)0.095 (4)0.011 (3)0.015 (3)0.001 (3)
C18C0.063 (3)0.104 (4)0.104 (4)0.022 (3)0.000 (3)0.003 (4)
C5C0.050 (2)0.066 (3)0.060 (3)0.000 (2)0.008 (2)0.013 (2)
C6C0.052 (3)0.087 (3)0.083 (4)0.002 (3)0.006 (3)0.025 (3)
C7C0.078 (3)0.073 (3)0.085 (4)0.014 (3)0.027 (3)0.026 (3)
C8C0.096 (4)0.068 (3)0.053 (3)0.009 (3)0.014 (3)0.004 (2)
C14C0.065 (3)0.060 (3)0.055 (3)0.000 (2)0.000 (2)0.005 (2)
C13C0.050 (2)0.070 (3)0.041 (2)0.001 (2)0.0041 (19)0.005 (2)
C15C0.055 (3)0.089 (3)0.049 (3)0.011 (2)0.006 (2)0.010 (2)
C16C0.062 (3)0.096 (3)0.056 (3)0.016 (3)0.001 (3)0.005 (3)
C1C0.053 (3)0.092 (4)0.073 (3)0.014 (3)0.010 (2)0.003 (3)
C2C0.060 (3)0.082 (3)0.083 (4)0.022 (3)0.004 (3)0.001 (3)
O1S0.146 (6)0.215 (7)0.222 (8)0.021 (6)0.019 (6)0.047 (7)
C3S0.096 (6)0.152 (7)0.153 (9)0.030 (5)0.052 (6)0.001 (6)
C12B0.046 (2)0.052 (2)0.052 (2)0.0058 (18)0.0089 (19)0.0028 (19)
C11B0.052 (2)0.075 (3)0.061 (3)0.002 (2)0.003 (2)0.012 (2)
C10B0.063 (3)0.096 (3)0.063 (3)0.006 (3)0.002 (2)0.030 (3)
C9B0.051 (2)0.074 (3)0.069 (3)0.009 (2)0.000 (2)0.024 (2)
N1B0.056 (2)0.084 (3)0.059 (2)0.002 (2)0.0060 (19)0.010 (2)
C17B0.071 (4)0.153 (6)0.065 (3)0.010 (4)0.011 (3)0.014 (4)
C2B0.050 (3)0.078 (3)0.071 (3)0.002 (2)0.016 (2)0.004 (3)
C1B0.065 (3)0.095 (3)0.055 (3)0.001 (3)0.016 (2)0.006 (3)
C13B0.045 (2)0.048 (2)0.053 (2)0.0065 (17)0.0048 (19)0.0074 (18)
C5B0.046 (2)0.057 (2)0.055 (2)0.0102 (18)0.004 (2)0.001 (2)
C6B0.056 (3)0.068 (3)0.068 (3)0.002 (2)0.002 (2)0.008 (2)
C7B0.064 (3)0.049 (2)0.113 (4)0.000 (2)0.015 (3)0.007 (3)
C8B0.055 (3)0.050 (2)0.102 (4)0.0072 (19)0.013 (3)0.017 (3)
C14B0.043 (2)0.053 (2)0.069 (3)0.0095 (17)0.009 (2)0.012 (2)
C16B0.062 (3)0.061 (3)0.064 (3)0.003 (2)0.004 (2)0.000 (2)
C15B0.055 (2)0.047 (2)0.056 (2)0.0060 (18)0.006 (2)0.0039 (19)
C18B0.062 (7)0.156 (11)0.070 (6)0.013 (7)0.017 (5)0.005 (7)
C20C0.097 (5)0.208 (9)0.123 (6)0.071 (6)0.015 (5)0.020 (6)
C19C0.091 (5)0.138 (6)0.141 (6)0.041 (5)0.005 (4)0.004 (6)
C20B0.077 (8)0.235 (17)0.086 (7)0.007 (10)0.005 (6)0.013 (8)
C1S0.164 (9)0.178 (9)0.158 (9)0.038 (8)0.053 (8)0.033 (8)
C2S0.237 (14)0.232 (13)0.099 (7)0.080 (12)0.026 (8)0.008 (8)
C4S0.137 (9)0.339 (17)0.121 (8)0.032 (11)0.002 (7)0.009 (10)
C18'0.036 (13)0.092 (17)0.087 (16)0.016 (11)0.012 (11)0.010 (13)
C20'0.058 (15)0.12 (2)0.092 (18)0.010 (13)0.020 (12)0.016 (15)
Geometric parameters (Å, º) top
C19B—C20B1.427 (15)C9C—C14C1.532 (7)
C19B—C20'1.46 (3)C9C—H9C0.98
C19B—C18B1.496 (12)N1C—C17C1.463 (6)
C19B—C18'1.62 (3)N1C—C16C1.464 (6)
C19B—H19A0.97C17C—C18C1.478 (8)
C19B—H19B0.97C17C—H17C0.97
C19B—H19'0.97C17C—H17D0.97
C19B—H19"0.97C18C—C19C1.494 (8)
O1A—C3A1.373 (5)C18C—C20C1.497 (10)
O1A—H1OA0.82C18C—H18C0.98
O2A—C4A1.387 (5)C5C—C6C1.536 (7)
O2A—C5A1.461 (5)C5C—C13C1.546 (6)
O4A—C14A1.439 (5)C5C—H5C0.98
O4A—H4OA0.82C6C—C7C1.483 (8)
O3A—C6A1.217 (5)C7C—C8C1.523 (8)
O1C—C3C1.380 (6)C7C—H7C10.97
O1C—H1OC0.82C7C—H7C20.97
O2C—C4C1.400 (5)C8C—C14C1.531 (6)
O2C—C5C1.465 (6)C8C—H8C10.97
O3C—C6C1.215 (6)C8C—H8C20.97
O4C—C14C1.443 (5)C14C—C13C1.533 (6)
O4C—H4OC0.82C13C—C15C1.538 (6)
O1B—C3B1.359 (5)C15C—C16C1.520 (7)
O1B—H1OB0.82C15C—H15C0.97
O2B—C4B1.391 (5)C15C—H15D0.97
O2B—C5B1.467 (4)C16C—H16C0.97
O4B—C14B1.446 (5)C16C—H16D0.97
O4B—H4OB0.82C1C—C2C1.363 (7)
C13A—C12A1.503 (5)C1C—H1C0.93
C13A—C15A1.536 (5)C2C—H2C0.93
C13A—C14A1.539 (5)O1S—C3S1.210 (10)
C13A—C5A1.549 (5)C3S—C4S1.406 (13)
N1A—C16A1.457 (5)C12B—C11B1.363 (6)
N1A—C17A1.462 (6)C12B—C13B1.508 (5)
N1A—C9A1.477 (5)C11B—C1B1.406 (7)
O3B—C6B1.195 (6)C11B—C10B1.515 (7)
C3B—C4B1.376 (6)C10B—C9B1.545 (7)
C3B—C2B1.380 (7)C10B—H10E0.97
C4B—C12B1.381 (6)C10B—H10F0.97
O2S—C3S1.268 (11)C9B—N1B1.484 (6)
O2S—C2S1.424 (11)C9B—C14B1.548 (7)
C3A—C4A1.376 (6)C9B—H9B0.98
C3A—C2A1.386 (7)N1B—C16B1.473 (6)
C4A—C12A1.369 (6)N1B—C17B1.483 (7)
C12A—C11A1.378 (6)C17B—C18B1.460 (13)
C15A—C16A1.514 (6)C17B—C18'1.61 (3)
C15A—H15A0.97C17B—H17E0.97
C15A—H15B0.97C17B—H17F0.97
C16A—H16A0.97C2B—C1B1.391 (7)
C16A—H16B0.97C2B—H2B0.93
C17A—C18A1.489 (8)C1B—H1B0.93
C17A—H17A0.97C13B—C15B1.526 (6)
C17A—H17B0.97C13B—C14B1.528 (5)
C18A—C20A1.436 (8)C13B—C5B1.553 (6)
C18A—C19A1.480 (8)C5B—C6B1.527 (6)
C18A—H18A0.98C5B—H5B0.98
C20A—C19A1.454 (8)C6B—C7B1.503 (7)
C20A—H20A0.97C7B—C8B1.532 (8)
C20A—H20B0.97C7B—H7B10.97
C5A—C6A1.522 (6)C7B—H7B20.97
C5A—H5A0.98C8B—C14B1.511 (6)
C19A—H19C0.97C8B—H8B10.97
C19A—H19D0.97C8B—H8B20.97
C9A—C14A1.546 (6)C16B—C15B1.508 (6)
C9A—C10A1.549 (6)C16B—H16E0.97
C9A—H9A0.98C16B—H16F0.97
C10A—C11A1.504 (6)C15B—H15E0.97
C10A—H10A0.97C15B—H15F0.97
C10A—H10B0.97C18B—C20B1.45 (2)
C11A—C1A1.392 (6)C18B—H18B0.98
C1A—C2A1.376 (7)C20C—C19C1.502 (11)
C1A—H1A0.93C20C—H20C0.97
C2A—H2A0.93C20C—H20D0.97
C14A—C8A1.508 (5)C19C—H19E0.97
C8A—C7A1.529 (6)C19C—H19F0.97
C8A—H8A10.97C20B—H20E0.97
C8A—H8A20.97C20B—H20F0.97
C7A—C6A1.484 (7)C1S—C2S1.419 (14)
C7A—H7A10.97C1S—H1S10.96
C7A—H7A20.97C1S—H1S20.96
C3C—C4C1.357 (6)C1S—H1S30.96
C3C—C2C1.396 (7)C2S—H2S10.97
C4C—C12C1.362 (6)C2S—H2S20.97
C12C—C11C1.373 (6)C4S—H4S10.96
C12C—C13C1.494 (6)C4S—H4S20.96
C11C—C1C1.400 (7)C4S—H4S30.96
C11C—C10C1.494 (7)C18'—C20'1.53 (5)
C10C—C9C1.534 (7)C18'—H18'0.98
C10C—H10C0.97C20'—H20G0.97
C10C—H10D0.97C20'—H20H0.97
C9C—N1C1.482 (6)
C20B—C19B—C18B59.5 (9)C6C—C7C—C8C111.7 (4)
C20'—C19B—C18'59.4 (17)C6C—C7C—H7C1109.3
C20B—C19B—H19A117.8C8C—C7C—H7C1109.3
C18B—C19B—H19A117.8C6C—C7C—H7C2109.3
C20B—C19B—H19B117.8C8C—C7C—H7C2109.3
C18B—C19B—H19B117.8H7C1—C7C—H7C2107.9
H19A—C19B—H19B115C7C—C8C—C14C111.0 (4)
C20'—C19B—H19'116.5C7C—C8C—H8C1109.4
C18'—C19B—H19'118.2C14C—C8C—H8C1109.4
C20'—C19B—H19"118.1C7C—C8C—H8C2109.4
C18'—C19B—H19"117.8C14C—C8C—H8C2109.4
H19'—C19B—H19"115.4H8C1—C8C—H8C2108
C3A—O1A—H1OA109.5O4C—C14C—C8C105.9 (4)
C4A—O2A—C5A103.8 (3)O4C—C14C—C9C107.8 (4)
C14A—O4A—H4OA109.5C8C—C14C—C9C113.7 (4)
C3C—O1C—H1OC109.5O4C—C14C—C13C112.3 (4)
C4C—O2C—C5C104.3 (3)C8C—C14C—C13C110.9 (4)
C14C—O4C—H4OC109.5C9C—C14C—C13C106.4 (4)
C3B—O1B—H1OB109.5C12C—C13C—C14C108.1 (3)
C4B—O2B—C5B104.0 (3)C12C—C13C—C15C110.5 (4)
C14B—O4B—H4OB109.5C14C—C13C—C15C109.2 (4)
C12A—C13A—C15A110.9 (3)C12C—C13C—C5C98.2 (3)
C12A—C13A—C14A108.0 (3)C14C—C13C—C5C117.8 (4)
C15A—C13A—C14A109.2 (3)C15C—C13C—C5C112.4 (4)
C12A—C13A—C5A98.2 (3)C16C—C15C—C13C110.6 (4)
C15A—C13A—C5A112.7 (3)C16C—C15C—H15C109.5
C14A—C13A—C5A117.3 (3)C13C—C15C—H15C109.5
C16A—N1A—C17A113.1 (4)C16C—C15C—H15D109.5
C16A—N1A—C9A112.1 (3)C13C—C15C—H15D109.5
C17A—N1A—C9A112.9 (3)H15C—C15C—H15D108.1
O1B—C3B—C4B125.1 (4)N1C—C16C—C15C112.1 (4)
O1B—C3B—C2B119.4 (4)N1C—C16C—H16C109.2
C4B—C3B—C2B115.5 (4)C15C—C16C—H16C109.2
C3B—C4B—C12B121.5 (4)N1C—C16C—H16D109.2
C3B—C4B—O2B126.8 (4)C15C—C16C—H16D109.2
C12B—C4B—O2B111.7 (3)H16C—C16C—H16D107.9
C3S—O2S—C2S119.8 (9)C2C—C1C—C11C121.3 (4)
O1A—C3A—C4A123.2 (4)C2C—C1C—H1C119.4
O1A—C3A—C2A119.9 (4)C11C—C1C—H1C119.4
C4A—C3A—C2A116.8 (4)C1C—C2C—C3C121.9 (5)
C12A—C4A—C3A120.4 (4)C1C—C2C—H2C119.1
C12A—C4A—O2A112.5 (3)C3C—C2C—H2C119.1
C3A—C4A—O2A127.0 (4)O1S—C3S—O2S121.4 (11)
C4A—C12A—C11A124.0 (4)O1S—C3S—C4S118.8 (11)
C4A—C12A—C13A108.7 (3)O2S—C3S—C4S118.4 (9)
C11A—C12A—C13A127.2 (4)C11B—C12B—C4B123.9 (4)
C16A—C15A—C13A110.8 (3)C11B—C12B—C13B126.9 (4)
C16A—C15A—H15A109.5C4B—C12B—C13B109.2 (3)
C13A—C15A—H15A109.5C12B—C11B—C1B115.4 (4)
C16A—C15A—H15B109.5C12B—C11B—C10B118.8 (4)
C13A—C15A—H15B109.5C1B—C11B—C10B125.7 (4)
H15A—C15A—H15B108.1C11B—C10B—C9B113.1 (4)
N1A—C16A—C15A111.6 (4)C11B—C10B—H10E109
N1A—C16A—H16A109.3C9B—C10B—H10E109
C15A—C16A—H16A109.3C11B—C10B—H10F109
N1A—C16A—H16B109.3C9B—C10B—H10F109
C15A—C16A—H16B109.3H10E—C10B—H10F107.8
H16A—C16A—H16B108N1B—C9B—C10B116.1 (4)
N1A—C17A—C18A112.6 (5)N1B—C9B—C14B104.9 (3)
N1A—C17A—H17A109.1C10B—C9B—C14B115.1 (4)
C18A—C17A—H17A109.1N1B—C9B—H9B106.7
N1A—C17A—H17B109.1C10B—C9B—H9B106.7
C18A—C17A—H17B109.1C14B—C9B—H9B106.7
H17A—C17A—H17B107.8C16B—N1B—C17B111.0 (5)
C20A—C18A—C19A59.8 (4)C16B—N1B—C9B112.4 (3)
C20A—C18A—C17A119.8 (6)C17B—N1B—C9B112.5 (4)
C19A—C18A—C17A118.2 (6)C18B—C17B—N1B115.3 (6)
C20A—C18A—H18A115.8N1B—C17B—C18'108.3 (11)
C19A—C18A—H18A115.8C18B—C17B—H17E108.4
C17A—C18A—H18A115.8N1B—C17B—H17E108.4
C18A—C20A—C19A61.6 (4)C18B—C17B—H17F108.4
C18A—C20A—H20A117.6N1B—C17B—H17F108.4
C19A—C20A—H20A117.6H17E—C17B—H17F107.5
C18A—C20A—H20B117.6C3B—C2B—C1B123.4 (4)
C19A—C20A—H20B117.6C3B—C2B—H2B118.3
H20A—C20A—H20B114.7C1B—C2B—H2B118.3
O2A—C5A—C6A108.8 (3)C2B—C1B—C11B120.3 (4)
O2A—C5A—C13A104.9 (3)C2B—C1B—H1B119.9
C6A—C5A—C13A113.6 (3)C11B—C1B—H1B119.9
O2A—C5A—H5A109.8C12B—C13B—C15B110.2 (3)
C6A—C5A—H5A109.8C12B—C13B—C14B108.6 (3)
C13A—C5A—H5A109.8C15B—C13B—C14B109.1 (3)
C20A—C19A—C18A58.6 (4)C12B—C13B—C5B97.3 (3)
C20A—C19A—H19C117.9C15B—C13B—C5B113.2 (3)
C18A—C19A—H19C117.9C14B—C13B—C5B117.6 (3)
C20A—C19A—H19D117.9O2B—C5B—C6B108.6 (3)
C18A—C19A—H19D117.9O2B—C5B—C13B105.2 (3)
H19C—C19A—H19D115.1C6B—C5B—C13B113.2 (4)
N1A—C9A—C14A105.1 (3)O2B—C5B—H5B109.9
N1A—C9A—C10A116.6 (4)C6B—C5B—H5B109.9
C14A—C9A—C10A114.5 (3)C13B—C5B—H5B109.9
N1A—C9A—H9A106.7O3B—C6B—C7B122.9 (5)
C14A—C9A—H9A106.7O3B—C6B—C5B121.5 (4)
C10A—C9A—H9A106.7C7B—C6B—C5B115.5 (4)
C11A—C10A—C9A114.6 (3)C6B—C7B—C8B109.3 (4)
C11A—C10A—H10A108.6C6B—C7B—H7B1109.8
C9A—C10A—H10A108.6C8B—C7B—H7B1109.8
C11A—C10A—H10B108.6C6B—C7B—H7B2109.8
C9A—C10A—H10B108.6C8B—C7B—H7B2109.8
H10A—C10A—H10B107.6H7B1—C7B—H7B2108.3
C12A—C11A—C1A115.2 (4)C14B—C8B—C7B110.6 (4)
C12A—C11A—C10A117.9 (4)C14B—C8B—H8B1109.5
C1A—C11A—C10A126.7 (4)C7B—C8B—H8B1109.5
C2A—C1A—C11A121.4 (5)C14B—C8B—H8B2109.5
C2A—C1A—H1A119.3C7B—C8B—H8B2109.5
C11A—C1A—H1A119.3H8B1—C8B—H8B2108.1
C1A—C2A—C3A122.1 (4)O4B—C14B—C8B106.1 (4)
C1A—C2A—H2A119O4B—C14B—C13B110.9 (3)
C3A—C2A—H2A119C8B—C14B—C13B112.5 (4)
O4A—C14A—C8A106.8 (3)O4B—C14B—C9B107.2 (3)
O4A—C14A—C13A111.1 (3)C8B—C14B—C9B114.1 (4)
C8A—C14A—C13A111.8 (3)C13B—C14B—C9B106.0 (4)
O4A—C14A—C9A107.5 (3)N1B—C16B—C15B110.9 (4)
C8A—C14A—C9A113.9 (3)N1B—C16B—H16E109.5
C13A—C14A—C9A105.7 (3)C15B—C16B—H16E109.5
C14A—C8A—C7A110.2 (3)N1B—C16B—H16F109.5
C14A—C8A—H8A1109.6C15B—C16B—H16F109.5
C7A—C8A—H8A1109.6H16E—C16B—H16F108
C14A—C8A—H8A2109.6C16B—C15B—C13B111.0 (4)
C7A—C8A—H8A2109.6C16B—C15B—H15E109.4
H8A1—C8A—H8A2108.1C13B—C15B—H15E109.4
C6A—C7A—C8A111.2 (4)C16B—C15B—H15F109.4
C6A—C7A—H7A1109.4C13B—C15B—H15F109.4
C8A—C7A—H7A1109.4H15E—C15B—H15F108
C6A—C7A—H7A2109.4C20B—C18B—C17B115.5 (14)
C8A—C7A—H7A2109.4C20B—C18B—C19B57.9 (7)
H7A1—C7A—H7A2108C17B—C18B—C19B118.2 (9)
O3A—C6A—C7A122.0 (5)C20B—C18B—H18B117.3
O3A—C6A—C5A120.0 (4)C17B—C18B—H18B117.3
C7A—C6A—C5A118.0 (4)C19B—C18B—H18B117.3
C4C—C3C—O1C125.1 (4)C18C—C20C—C19C59.8 (5)
C4C—C3C—C2C116.4 (5)C18C—C20C—H20C117.8
O1C—C3C—C2C118.5 (5)C19C—C20C—H20C117.8
C3C—C4C—C12C121.9 (4)C18C—C20C—H20D117.8
C3C—C4C—O2C126.6 (4)C19C—C20C—H20D117.8
C12C—C4C—O2C111.5 (4)H20C—C20C—H20D114.9
C4C—C12C—C11C123.1 (4)C18C—C19C—C20C60.0 (5)
C4C—C12C—C13C110.0 (4)C18C—C19C—H19E117.8
C11C—C12C—C13C127.0 (4)C20C—C19C—H19E117.8
C12C—C11C—C1C115.4 (4)C18C—C19C—H19F117.8
C12C—C11C—C10C118.1 (4)C20C—C19C—H19F117.8
C1C—C11C—C10C126.1 (4)H19E—C19C—H19F114.9
C11C—C10C—C9C114.1 (4)C19B—C20B—C18B62.6 (8)
C11C—C10C—H10C108.7C19B—C20B—H20E117.5
C9C—C10C—H10C108.7C18B—C20B—H20E117.5
C11C—C10C—H10D108.7C19B—C20B—H20F117.5
C9C—C10C—H10D108.7C18B—C20B—H20F117.5
H10C—C10C—H10D107.6H20E—C20B—H20F114.6
N1C—C9C—C14C104.7 (4)C2S—C1S—H1S1109.5
N1C—C9C—C10C117.1 (5)C2S—C1S—H1S2109.5
C14C—C9C—C10C114.7 (4)H1S1—C1S—H1S2109.5
N1C—C9C—H9C106.5C2S—C1S—H1S3109.5
C14C—C9C—H9C106.5H1S1—C1S—H1S3109.5
C10C—C9C—H9C106.5H1S2—C1S—H1S3109.5
C17C—N1C—C16C113.4 (4)C1S—C2S—O2S110.4 (9)
C17C—N1C—C9C113.2 (4)C1S—C2S—H2S1109.6
C16C—N1C—C9C112.4 (4)O2S—C2S—H2S1109.6
N1C—C17C—C18C112.9 (5)C1S—C2S—H2S2109.6
N1C—C17C—H17C109O2S—C2S—H2S2109.6
C18C—C17C—H17C109H2S1—C2S—H2S2108.1
N1C—C17C—H17D109C3S—C4S—H4S1109.5
C18C—C17C—H17D109C3S—C4S—H4S2109.5
H17C—C17C—H17D107.8H4S1—C4S—H4S2109.5
C17C—C18C—C19C117.5 (6)C3S—C4S—H4S3109.5
C17C—C18C—C20C119.6 (7)H4S1—C4S—H4S3109.5
C19C—C18C—C20C60.3 (5)H4S2—C4S—H4S3109.5
C17C—C18C—H18C116C20'—C18'—C17B113 (2)
C19C—C18C—H18C116C20'—C18'—C19B55.2 (14)
C20C—C18C—H18C116C17B—C18'—C19B103.3 (15)
O2C—C5C—C6C108.3 (4)C20'—C18'—H18'122.1
O2C—C5C—C13C105.0 (3)C17B—C18'—H18'122.1
C6C—C5C—C13C114.3 (4)C19B—C18'—H18'122.1
O2C—C5C—H5C109.7C19B—C20'—C18'65.5 (16)
C6C—C5C—H5C109.7C19B—C20'—H20G117.2
C13C—C5C—H5C109.7C18'—C20'—H20G117.2
O3C—C6C—C7C123.7 (5)C19B—C20'—H20H117.2
O3C—C6C—C5C118.7 (6)C18'—C20'—H20H117.2
C7C—C6C—C5C117.6 (4)H20G—C20'—H20H114.2
O1B—C3B—C4B—C12B179.4 (4)C4C—C12C—C13C—C15C94.8 (4)
C2B—C3B—C4B—C12B1.3 (7)C11C—C12C—C13C—C15C84.6 (5)
O1B—C3B—C4B—O2B2.7 (7)C4C—C12C—C13C—C5C22.8 (5)
C2B—C3B—C4B—O2B176.6 (4)C11C—C12C—C13C—C5C157.7 (4)
C5B—O2B—C4B—C3B160.7 (4)O4C—C14C—C13C—C12C173.7 (4)
C5B—O2B—C4B—C12B17.4 (4)C8C—C14C—C13C—C12C68.0 (5)
O1A—C3A—C4A—C12A178.6 (4)C9C—C14C—C13C—C12C56.0 (4)
C2A—C3A—C4A—C12A2.5 (7)O4C—C14C—C13C—C15C53.5 (5)
O1A—C3A—C4A—O2A4.8 (8)C8C—C14C—C13C—C15C171.7 (4)
C2A—C3A—C4A—O2A174.1 (4)C9C—C14C—C13C—C15C64.3 (5)
C5A—O2A—C4A—C12A18.9 (4)O4C—C14C—C13C—C5C76.2 (5)
C5A—O2A—C4A—C3A158.0 (5)C8C—C14C—C13C—C5C42.0 (5)
C3A—C4A—C12A—C11A3.8 (7)C9C—C14C—C13C—C5C166.0 (4)
O2A—C4A—C12A—C11A173.3 (4)O2C—C5C—C13C—C12C31.8 (4)
C3A—C4A—C12A—C13A179.7 (4)C6C—C5C—C13C—C12C86.7 (4)
O2A—C4A—C12A—C13A3.2 (5)O2C—C5C—C13C—C14C147.3 (4)
C15A—C13A—C12A—C4A96.1 (4)C6C—C5C—C13C—C14C28.8 (5)
C14A—C13A—C12A—C4A144.3 (4)O2C—C5C—C13C—C15C84.4 (4)
C5A—C13A—C12A—C4A22.1 (4)C6C—C5C—C13C—C15C157.0 (4)
C15A—C13A—C12A—C11A87.6 (5)C12C—C13C—C15C—C16C65.2 (5)
C14A—C13A—C12A—C11A32.0 (5)C14C—C13C—C15C—C16C53.5 (5)
C5A—C13A—C12A—C11A154.2 (4)C5C—C13C—C15C—C16C173.8 (4)
C12A—C13A—C15A—C16A64.7 (4)C17C—N1C—C16C—C15C173.0 (4)
C14A—C13A—C15A—C16A54.3 (4)C9C—N1C—C16C—C15C57.1 (6)
C5A—C13A—C15A—C16A173.6 (3)C13C—C15C—C16C—N1C49.0 (6)
C17A—N1A—C16A—C15A172.6 (4)C12C—C11C—C1C—C2C0.2 (7)
C9A—N1A—C16A—C15A58.4 (5)C10C—C11C—C1C—C2C172.3 (5)
C13A—C15A—C16A—N1A50.4 (5)C11C—C1C—C2C—C3C2.6 (8)
C16A—N1A—C17A—C18A85.4 (6)C4C—C3C—C2C—C1C3.1 (8)
C9A—N1A—C17A—C18A146.0 (5)O1C—C3C—C2C—C1C174.5 (5)
N1A—C17A—C18A—C20A84.1 (7)C2S—O2S—C3S—O1S9.8 (17)
N1A—C17A—C18A—C19A153.6 (5)C2S—O2S—C3S—C4S176.3 (12)
C17A—C18A—C20A—C19A107.3 (7)C3B—C4B—C12B—C11B3.3 (7)
C4A—O2A—C5A—C6A89.4 (4)O2B—C4B—C12B—C11B174.9 (4)
C4A—O2A—C5A—C13A32.5 (4)C3B—C4B—C12B—C13B176.1 (4)
C12A—C13A—C5A—O2A32.8 (4)O2B—C4B—C12B—C13B5.6 (5)
C15A—C13A—C5A—O2A84.1 (4)C4B—C12B—C11B—C1B3.1 (7)
C14A—C13A—C5A—O2A148.0 (3)C13B—C12B—C11B—C1B176.2 (4)
C12A—C13A—C5A—C6A86.0 (4)C4B—C12B—C11B—C10B172.5 (4)
C15A—C13A—C5A—C6A157.2 (3)C13B—C12B—C11B—C10B8.2 (7)
C14A—C13A—C5A—C6A29.2 (5)C12B—C11B—C10B—C9B8.3 (7)
C17A—C18A—C19A—C20A109.9 (7)C1B—C11B—C10B—C9B176.6 (5)
C16A—N1A—C9A—C14A66.9 (4)C11B—C10B—C9B—N1B86.6 (5)
C17A—N1A—C9A—C14A164.0 (4)C11B—C10B—C9B—C14B36.5 (6)
C16A—N1A—C9A—C10A61.2 (5)C10B—C9B—N1B—C16B62.6 (5)
C17A—N1A—C9A—C10A68.0 (5)C14B—C9B—N1B—C16B65.7 (4)
N1A—C9A—C10A—C11A90.8 (5)C10B—C9B—N1B—C17B63.6 (6)
C14A—C9A—C10A—C11A32.5 (5)C14B—C9B—N1B—C17B168.1 (4)
C4A—C12A—C11A—C1A2.2 (7)C16B—N1B—C17B—C18B72.4 (9)
C13A—C12A—C11A—C1A178.0 (4)C9B—N1B—C17B—C18B160.6 (8)
C4A—C12A—C11A—C10A173.8 (4)C16B—N1B—C17B—C18'106.1 (13)
C13A—C12A—C11A—C10A2.0 (6)C9B—N1B—C17B—C18'126.9 (12)
C9A—C10A—C11A—C12A1.4 (6)O1B—C3B—C2B—C1B178.8 (5)
C9A—C10A—C11A—C1A176.9 (5)C4B—C3B—C2B—C1B0.5 (7)
C12A—C11A—C1A—C2A0.5 (7)C3B—C2B—C1B—C11B0.6 (8)
C10A—C11A—C1A—C2A176.1 (5)C12B—C11B—C1B—C2B1.2 (7)
C11A—C1A—C2A—C3A1.6 (8)C10B—C11B—C1B—C2B174.0 (5)
O1A—C3A—C2A—C1A178.8 (5)C11B—C12B—C13B—C15B85.6 (5)
C4A—C3A—C2A—C1A0.1 (7)C4B—C12B—C13B—C15B93.8 (4)
C12A—C13A—C14A—O4A173.7 (3)C11B—C12B—C13B—C14B33.9 (6)
C15A—C13A—C14A—O4A53.0 (4)C4B—C12B—C13B—C14B146.7 (4)
C5A—C13A—C14A—O4A76.7 (4)C11B—C12B—C13B—C5B156.3 (4)
C12A—C13A—C14A—C8A67.0 (4)C4B—C12B—C13B—C5B24.3 (4)
C15A—C13A—C14A—C8A172.2 (3)C4B—O2B—C5B—C6B88.6 (4)
C5A—C13A—C14A—C8A42.6 (5)C4B—O2B—C5B—C13B32.8 (4)
C12A—C13A—C14A—C9A57.4 (4)C12B—C13B—C5B—O2B34.1 (4)
C15A—C13A—C14A—C9A63.3 (4)C15B—C13B—C5B—O2B81.6 (4)
C5A—C13A—C14A—C9A167.1 (3)C14B—C13B—C5B—O2B149.6 (3)
N1A—C9A—C14A—O4A50.7 (4)C12B—C13B—C5B—C6B84.3 (4)
C10A—C9A—C14A—O4A180.0 (3)C15B—C13B—C5B—C6B160.0 (4)
N1A—C9A—C14A—C8A168.8 (3)C14B—C13B—C5B—C6B31.2 (5)
C10A—C9A—C14A—C8A61.9 (5)O2B—C5B—C6B—O3B19.5 (7)
N1A—C9A—C14A—C13A68.0 (4)C13B—C5B—C6B—O3B135.9 (5)
C10A—C9A—C14A—C13A61.3 (4)O2B—C5B—C6B—C7B156.1 (4)
O4A—C14A—C8A—C7A64.5 (4)C13B—C5B—C6B—C7B39.8 (6)
C13A—C14A—C8A—C7A57.2 (5)O3B—C6B—C7B—C8B119.6 (6)
C9A—C14A—C8A—C7A177.0 (4)C5B—C6B—C7B—C8B55.9 (6)
C14A—C8A—C7A—C6A60.6 (5)C6B—C7B—C8B—C14B63.1 (5)
C8A—C7A—C6A—O3A129.6 (5)C7B—C8B—C14B—O4B66.4 (5)
C8A—C7A—C6A—C5A49.0 (5)C7B—C8B—C14B—C13B55.0 (5)
O2A—C5A—C6A—O3A29.3 (5)C7B—C8B—C14B—C9B175.8 (4)
C13A—C5A—C6A—O3A145.7 (4)C12B—C13B—C14B—O4B171.9 (3)
O2A—C5A—C6A—C7A149.5 (4)C15B—C13B—C14B—O4B51.8 (5)
C13A—C5A—C6A—C7A33.0 (5)C5B—C13B—C14B—O4B78.9 (4)
O1C—C3C—C4C—C12C176.6 (5)C12B—C13B—C14B—C8B69.5 (5)
C2C—C3C—C4C—C12C0.9 (7)C15B—C13B—C14B—C8B170.4 (4)
O1C—C3C—C4C—O2C0.2 (8)C5B—C13B—C14B—C8B39.7 (5)
C2C—C3C—C4C—O2C177.6 (4)C12B—C13B—C14B—C9B55.9 (4)
C5C—O2C—C4C—C3C160.7 (5)C15B—C13B—C14B—C9B64.3 (4)
C5C—O2C—C4C—C12C16.4 (5)C5B—C13B—C14B—C9B165.0 (4)
C3C—C4C—C12C—C11C2.0 (7)N1B—C9B—C14B—O4B51.0 (4)
O2C—C4C—C12C—C11C175.3 (4)C10B—C9B—C14B—O4B179.9 (4)
C3C—C4C—C12C—C13C177.5 (4)N1B—C9B—C14B—C8B168.2 (3)
O2C—C4C—C12C—C13C5.2 (5)C10B—C9B—C14B—C8B62.9 (5)
C4C—C12C—C11C—C1C2.4 (7)N1B—C9B—C14B—C13B67.5 (4)
C13C—C12C—C11C—C1C177.0 (4)C10B—C9B—C14B—C13B61.4 (5)
C4C—C12C—C11C—C10C170.7 (5)C17B—N1B—C16B—C15B175.1 (4)
C13C—C12C—C11C—C10C9.9 (7)C9B—N1B—C16B—C15B57.9 (5)
C12C—C11C—C10C—C9C9.3 (7)N1B—C16B—C15B—C13B51.1 (5)
C1C—C11C—C10C—C9C178.3 (5)C12B—C13B—C15B—C16B63.2 (4)
C11C—C10C—C9C—N1C86.7 (6)C14B—C13B—C15B—C16B56.0 (5)
C11C—C10C—C9C—C14C36.7 (6)C5B—C13B—C15B—C16B170.9 (4)
C14C—C9C—N1C—C17C163.7 (4)N1B—C17B—C18B—C20B96.2 (9)
C10C—C9C—N1C—C17C67.9 (5)C18'—C17B—C18B—C20B12 (2)
C14C—C9C—N1C—C16C66.2 (5)N1B—C17B—C18B—C19B161.9 (10)
C10C—C9C—N1C—C16C62.1 (5)C18'—C17B—C18B—C19B78 (2)
C16C—N1C—C17C—C18C67.2 (6)C20'—C19B—C18B—C20B77.1 (18)
C9C—N1C—C17C—C18C163.3 (5)C18'—C19B—C18B—C20B25 (2)
N1C—C17C—C18C—C19C168.1 (6)C20B—C19B—C18B—C17B103.8 (16)
N1C—C17C—C18C—C20C98.4 (7)C20'—C19B—C18B—C17B179 (3)
C4C—O2C—C5C—C6C92.0 (4)C18'—C19B—C18B—C17B79 (3)
C4C—O2C—C5C—C13C30.5 (4)C17C—C18C—C20C—C19C106.7 (7)
O2C—C5C—C6C—O3C32.3 (6)C17C—C18C—C19C—C20C110.1 (8)
C13C—C5C—C6C—O3C149.0 (5)C20'—C19B—C20B—C18B53.8 (12)
O2C—C5C—C6C—C7C148.0 (4)C18'—C19B—C20B—C18B24 (2)
C13C—C5C—C6C—C7C31.3 (6)C17B—C18B—C20B—C19B108.6 (10)
O3C—C6C—C7C—C8C133.0 (5)C3S—O2S—C2S—C1S168.5 (10)
C5C—C6C—C7C—C8C47.3 (6)C18B—C17B—C18'—C20'2.8 (12)
C6C—C7C—C8C—C14C60.2 (5)N1B—C17B—C18'—C20'106.0 (18)
C7C—C8C—C14C—O4C65.2 (5)C18B—C17B—C18'—C19B54.7 (18)
C7C—C8C—C14C—C9C176.6 (4)N1B—C17B—C18'—C19B163.5 (11)
C7C—C8C—C14C—C13C56.9 (5)C20B—C19B—C18'—C20'82 (2)
N1C—C9C—C14C—O4C51.9 (5)C18B—C19B—C18'—C20'55 (2)
C10C—C9C—C14C—O4C178.3 (4)C20B—C19B—C18'—C17B169 (3)
N1C—C9C—C14C—C8C169.0 (4)C20'—C19B—C18'—C17B109 (2)
C10C—C9C—C14C—C8C61.2 (6)C18B—C19B—C18'—C17B53.5 (17)
N1C—C9C—C14C—C13C68.7 (4)C20B—C19B—C20'—C18'37.9 (11)
C10C—C9C—C14C—C13C61.1 (5)C18B—C19B—C20'—C18'36.6 (13)
C4C—C12C—C13C—C14C145.8 (4)C17B—C18'—C20'—C19B90.8 (18)
C11C—C12C—C13C—C14C34.8 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1OA···O4Ai0.821.902.710 (5)168
O4A—H4OA···O2Aii0.822.432.904 (4)118
O1B—H1OB···O4Biii0.821.922.728 (5)170
O4B—H4OB···O2Biv0.822.392.942 (4)126
O1C—H1OC···O4Cv0.821.882.672 (6)164
O4C—H4OC···O2Cvi0.822.843.125 (4)103
C8B—H8B2···O1S0.972.543.395 (10)147
C20B—H20E···O1Bvii0.972.663.589 (15)160
C18C—H18C···O3Cvi0.982.633.501 (7)148
C19A—H19D···Cg(A)Cviii0.972.843.772 (7)163
Symmetry codes: (i) x+1/2, y+3/2, z+2; (ii) x1/2, y+3/2, z+2; (iii) x+1/2, y+1/2, z+2; (iv) x1/2, y+1/2, z+2; (v) x+1, y+1/2, z+3/2; (vi) x+1, y1/2, z+3/2; (vii) x1, y, z; (viii) x, y+1/2, z+3/2.
(4R,4aS,7aR,12bS)-3-Cyclopropylmethyl-4a,9-dihydroxy-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one diethyl ether hemisolvate (naltrexone_Et2O) top
Crystal data top
2C20H23NO4·C4H10ODx = 1.142 Mg m3
Mr = 756.91Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, P212121Cell parameters from 2455 reflections
a = 12.5992 (2) Åθ = 3.8–50.1°
b = 13.1093 (3) ŵ = 0.64 mm1
c = 26.6586 (6) ÅT = 296 K
V = 4403.11 (16) Å3Needle, colourless
Z = 40.20 × 0.10 × 0.08 mm
F(000) = 1624
Data collection top
Bruker APEXII CCD
diffractometer
5222 reflections with I > 2σ(I)
CCD scansRint = 0.059
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
θmax = 66.5°, θmin = 3.3°
Tmin = 0.843, Tmax = 0.950h = 1414
22971 measured reflectionsk = 1315
7390 independent reflectionsl = 3131
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.065 w = 1/[σ2(Fo2) + (0.113P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.193(Δ/σ)max = 0.002
S = 1.10Δρmax = 0.53 e Å3
7390 reflectionsΔρmin = 0.26 e Å3
545 parametersAbsolute structure: Flack x determined using 1854 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
8 restraintsAbsolute structure parameter: 0.12 (17)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O1B0.2546 (3)0.9044 (3)0.00091 (17)0.0801 (11)
H1OB0.2670.85790.02060.12*
O2B0.4526 (3)0.7815 (3)0.00546 (13)0.0670 (10)
O3B0.4107 (4)0.6226 (4)0.0546 (2)0.1042 (16)
O4B0.7683 (2)0.7362 (3)0.07619 (14)0.0669 (9)
H4OB0.8140.77620.06660.1*
O1A0.8534 (3)0.8191 (3)0.77682 (17)0.0758 (10)
H1OA0.91540.82960.78450.114*
O2A0.9696 (3)1.0156 (3)0.76596 (15)0.0672 (9)
O4A0.9420 (3)1.3257 (3)0.68883 (15)0.0705 (10)
H4OA0.9111.36910.70540.106*
O3A1.0897 (5)0.9936 (5)0.6846 (2)0.1146 (17)
C12A0.8182 (4)1.0822 (4)0.73229 (19)0.0557 (11)
N1A0.7502 (4)1.3378 (3)0.72979 (18)0.0708 (12)
C19B1.0429 (5)1.0706 (7)0.1035 (4)0.109 (3)
H19A1.0371.06960.13980.13*
H19B1.08841.12360.090.13*
C18B0.9463 (7)1.0394 (7)0.0730 (4)0.119 (3)
H18B0.93881.07460.04080.142*
C17B0.8476 (5)1.0179 (6)0.0984 (3)0.097 (2)
H17A0.86341.00020.1330.116*
H17B0.80541.07970.09890.116*
N1B0.7834 (4)0.9358 (4)0.07652 (19)0.0750 (13)
C9B0.7061 (4)0.8938 (5)0.1122 (2)0.0686 (14)
H9B0.74510.87780.1430.082*
C10B0.6132 (4)0.9638 (6)0.1273 (2)0.0789 (17)
H10A0.63821.03380.12770.095*
H10B0.59150.94660.16120.095*
C11B0.5170 (4)0.9576 (5)0.0934 (2)0.0647 (13)
C12B0.5182 (4)0.8850 (4)0.05664 (19)0.0605 (12)
C4B0.4323 (4)0.8633 (4)0.02585 (19)0.0588 (12)
C3B0.3410 (4)0.9198 (5)0.0292 (2)0.0676 (14)
C5B0.5429 (4)0.7298 (4)0.01796 (18)0.0622 (12)
H5B0.58510.69390.00740.075*
C6B0.5002 (4)0.6551 (5)0.0567 (2)0.0701 (14)
C7B0.5751 (5)0.6276 (5)0.0984 (2)0.0784 (16)
H7B10.53970.58310.12210.094*
H7B20.63590.59150.08480.094*
C8B0.6122 (5)0.7241 (5)0.1250 (2)0.0762 (16)
H8B10.65760.70590.1530.091*
H8B20.55130.76060.13810.091*
C14B0.6727 (4)0.7921 (4)0.08904 (18)0.0615 (13)
C20B1.0388 (6)0.9724 (7)0.0768 (4)0.106 (2)
H20A1.03170.9110.09690.128*
H20B1.08290.96490.04720.128*
C16B0.7337 (5)0.9643 (5)0.0285 (2)0.0738 (15)
H16A0.68131.01720.03420.089*
H16B0.78730.99130.00590.089*
C15B0.6805 (4)0.8719 (5)0.00433 (19)0.0663 (13)
H15A0.63820.89390.02410.08*
H15B0.73440.82530.00790.08*
C13B0.6087 (4)0.8161 (4)0.04238 (17)0.0572 (12)
C1B0.4239 (4)1.0143 (5)0.0972 (2)0.0757 (16)
H1B0.41831.06460.12170.091*
C2B0.3389 (4)0.9965 (5)0.0648 (2)0.0752 (16)
H2B0.27891.03750.06730.09*
C3A0.8106 (4)0.9058 (4)0.75699 (19)0.0611 (12)
C4A0.8653 (4)0.9970 (4)0.75256 (19)0.0567 (12)
C11A0.7171 (4)1.0823 (4)0.7127 (2)0.0615 (12)
C10A0.6817 (5)1.1772 (4)0.6849 (2)0.0736 (15)
H10C0.61461.19970.69890.088*
H10D0.66931.15940.650.088*
C9A0.7610 (4)1.2671 (4)0.6868 (2)0.0687 (14)
H9A0.74921.30750.65630.082*
C17A0.6514 (5)1.3991 (5)0.7290 (3)0.0891 (19)
H17C0.59481.36010.74450.107*
H17D0.63141.41190.69440.107*
C18A0.6627 (6)1.4996 (6)0.7559 (3)0.099 (2)
H18A0.67871.4960.79180.118*
C19A0.5942 (5)1.5845 (5)0.7396 (3)0.0902 (19)
H19C0.54571.57220.71210.108*
H19D0.56811.63090.76520.108*
C5A0.9985 (4)1.1077 (4)0.7380 (2)0.0609 (12)
H5A1.05181.14670.75670.073*
C13A0.8951 (4)1.1696 (4)0.73411 (19)0.0566 (11)
C1A0.6618 (4)0.9901 (4)0.7174 (2)0.0716 (14)
H1A0.59260.98580.70550.086*
C2A0.7072 (4)0.9063 (4)0.7391 (2)0.0676 (14)
H2A0.66710.8470.7420.081*
C20A0.7084 (6)1.5861 (6)0.7285 (5)0.127 (3)
H20C0.73011.57490.6940.153*
H20D0.75251.63350.7470.153*
C16A0.7654 (5)1.2877 (5)0.7778 (2)0.0714 (14)
H16C0.71011.23710.78270.086*
H16D0.75971.33760.80450.086*
C15A0.8740 (4)1.2360 (4)0.78032 (19)0.0636 (12)
H15C0.87751.19390.81020.076*
H15D0.92881.28770.78280.076*
C14A0.8783 (4)1.2349 (4)0.6864 (2)0.0615 (12)
C8A0.9115 (5)1.1791 (5)0.6400 (2)0.0744 (15)
H8A10.90361.22350.61120.089*
H8A20.86591.12030.63520.089*
C7A1.0276 (6)1.1436 (5)0.6439 (2)0.0846 (19)
H7A11.04731.10870.61320.101*
H7A21.07331.20270.64750.101*
C6A1.0445 (5)1.0739 (5)0.6873 (2)0.0734 (15)
C5S0.965 (4)0.343 (2)0.9437 (12)0.24 (3)0.5
H5S11.01480.36270.91840.364*0.5
H5S20.97160.38640.97230.364*0.5
H5S30.97860.27330.95350.364*0.5
C7S0.664 (3)0.314 (2)0.9142 (10)0.184 (14)0.5
H7S10.67220.24650.90010.221*0.5
H7S20.67170.36140.88630.221*0.5
O2S0.755 (4)0.3299 (18)0.9445 (11)0.263 (17)0.5
C3S1.153 (3)0.343 (2)0.9293 (10)0.198 (17)0.5
H3S11.17590.40070.94960.238*0.5
H3S21.15140.28420.95110.238*0.5
C6S0.856 (4)0.350 (2)0.9234 (10)0.185 (16)0.5
H6S10.85110.42020.91180.222*0.5
H6S20.8580.30880.89330.222*0.5
C1S1.447 (4)0.320 (2)0.9016 (12)0.22 (2)0.5
H1S11.49110.33580.930.334*0.5
H1S21.45870.25110.89140.334*0.5
H1S31.46490.36540.87440.334*0.5
C2S1.334 (4)0.335 (3)0.9153 (15)0.29 (4)0.5
H2S11.32660.29180.94480.353*0.5
H2S21.33270.40390.92810.353*0.5
C8S0.555 (4)0.322 (2)0.9300 (13)0.221 (19)0.5
H8S10.50930.30780.9020.332*0.5
H8S20.54190.27340.95620.332*0.5
H8S30.54140.38950.94220.332*0.5
O1S1.233 (4)0.326 (2)0.8929 (11)0.38 (3)0.5
C4S1.043 (4)0.364 (2)0.9125 (16)0.32 (4)0.5
H4S10.99840.3740.94130.487*0.5
H4S21.04190.4240.8920.487*0.5
H4S31.01730.30680.89350.487*0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1B0.0473 (18)0.094 (3)0.099 (3)0.0078 (19)0.016 (2)0.016 (2)
O2B0.0496 (17)0.083 (3)0.068 (2)0.0083 (17)0.0125 (16)0.0143 (19)
O3B0.070 (3)0.120 (4)0.123 (4)0.033 (3)0.011 (3)0.011 (3)
O4B0.0438 (17)0.090 (3)0.066 (2)0.0082 (17)0.0036 (15)0.0003 (19)
O1A0.078 (2)0.0539 (19)0.095 (3)0.0006 (18)0.002 (2)0.013 (2)
O2A0.0568 (19)0.0612 (19)0.084 (2)0.0008 (16)0.0116 (17)0.0110 (18)
O4A0.080 (2)0.0555 (19)0.076 (2)0.0135 (19)0.0015 (19)0.0051 (18)
O3A0.117 (4)0.114 (4)0.113 (4)0.046 (3)0.009 (3)0.018 (3)
C12A0.052 (3)0.054 (3)0.061 (3)0.003 (2)0.003 (2)0.002 (2)
N1A0.072 (3)0.060 (2)0.080 (3)0.010 (2)0.016 (2)0.000 (2)
C19B0.065 (4)0.121 (6)0.140 (7)0.027 (4)0.001 (4)0.029 (5)
C18B0.086 (5)0.121 (7)0.149 (8)0.017 (5)0.007 (5)0.016 (6)
C17B0.057 (3)0.108 (5)0.126 (6)0.004 (3)0.006 (3)0.036 (5)
N1B0.057 (2)0.090 (3)0.078 (3)0.007 (2)0.006 (2)0.012 (3)
C9B0.052 (3)0.094 (4)0.060 (3)0.002 (3)0.007 (2)0.009 (3)
C10B0.058 (3)0.110 (5)0.069 (3)0.001 (3)0.005 (3)0.021 (3)
C11B0.052 (3)0.084 (4)0.058 (3)0.002 (2)0.002 (2)0.014 (3)
C12B0.044 (2)0.078 (3)0.059 (3)0.003 (2)0.003 (2)0.004 (3)
C4B0.046 (2)0.072 (3)0.059 (3)0.001 (2)0.003 (2)0.007 (2)
C3B0.042 (3)0.087 (4)0.074 (3)0.003 (3)0.005 (2)0.004 (3)
C5B0.045 (2)0.080 (3)0.061 (3)0.009 (2)0.003 (2)0.009 (3)
C6B0.060 (3)0.073 (3)0.078 (3)0.001 (3)0.003 (3)0.006 (3)
C7B0.063 (3)0.091 (4)0.082 (4)0.002 (3)0.010 (3)0.019 (3)
C8B0.065 (3)0.101 (4)0.062 (3)0.003 (3)0.000 (2)0.013 (3)
C14B0.042 (2)0.086 (4)0.056 (3)0.005 (2)0.002 (2)0.001 (3)
C20B0.077 (4)0.106 (5)0.136 (6)0.004 (4)0.022 (4)0.029 (5)
C16B0.058 (3)0.081 (4)0.082 (4)0.002 (3)0.009 (3)0.004 (3)
C15B0.054 (3)0.089 (4)0.057 (3)0.002 (3)0.004 (2)0.000 (3)
C13B0.044 (2)0.075 (3)0.053 (2)0.004 (2)0.0015 (19)0.004 (2)
C1B0.059 (3)0.090 (4)0.078 (3)0.011 (3)0.006 (3)0.016 (3)
C2B0.050 (3)0.089 (4)0.087 (4)0.012 (3)0.002 (3)0.013 (3)
C3A0.064 (3)0.058 (3)0.062 (3)0.000 (2)0.005 (2)0.003 (2)
C4A0.052 (3)0.055 (3)0.063 (3)0.003 (2)0.002 (2)0.002 (2)
C11A0.056 (3)0.062 (3)0.066 (3)0.003 (2)0.009 (2)0.001 (2)
C10A0.065 (3)0.072 (3)0.084 (4)0.004 (3)0.025 (3)0.006 (3)
C9A0.072 (3)0.062 (3)0.072 (3)0.000 (3)0.019 (3)0.006 (3)
C17A0.077 (4)0.069 (4)0.121 (5)0.012 (3)0.018 (4)0.001 (4)
C18A0.084 (4)0.084 (5)0.128 (6)0.017 (4)0.024 (4)0.002 (4)
C19A0.072 (4)0.081 (4)0.118 (5)0.017 (3)0.014 (4)0.017 (4)
C5A0.054 (3)0.056 (3)0.072 (3)0.007 (2)0.004 (2)0.001 (2)
C13A0.056 (3)0.054 (3)0.060 (3)0.003 (2)0.007 (2)0.005 (2)
C1A0.057 (3)0.074 (3)0.084 (4)0.007 (3)0.010 (3)0.005 (3)
C2A0.063 (3)0.056 (3)0.083 (3)0.012 (3)0.006 (3)0.001 (3)
C20A0.079 (5)0.094 (5)0.209 (11)0.010 (4)0.021 (6)0.018 (6)
C16A0.068 (3)0.072 (3)0.074 (3)0.003 (3)0.001 (3)0.002 (3)
C15A0.068 (3)0.064 (3)0.059 (3)0.002 (2)0.005 (2)0.002 (2)
C14A0.071 (3)0.052 (3)0.061 (3)0.008 (2)0.004 (2)0.003 (2)
C8A0.095 (4)0.071 (3)0.057 (3)0.012 (3)0.002 (3)0.002 (3)
C7A0.099 (5)0.070 (4)0.085 (4)0.019 (3)0.031 (4)0.012 (3)
C6A0.059 (3)0.073 (4)0.088 (4)0.002 (3)0.005 (3)0.011 (3)
C5S0.51 (8)0.081 (15)0.14 (2)0.05 (3)0.00 (4)0.043 (15)
C7S0.31 (4)0.13 (2)0.111 (17)0.03 (3)0.06 (3)0.009 (15)
O2S0.48 (6)0.127 (15)0.18 (2)0.00 (3)0.01 (3)0.003 (15)
C3S0.37 (5)0.123 (18)0.104 (15)0.10 (3)0.05 (3)0.008 (14)
C6S0.32 (5)0.115 (18)0.124 (18)0.07 (2)0.05 (2)0.058 (15)
C1S0.41 (7)0.110 (17)0.15 (2)0.08 (3)0.05 (3)0.049 (17)
C2S0.52 (9)0.14 (2)0.23 (4)0.14 (5)0.20 (6)0.06 (3)
C8S0.39 (6)0.105 (17)0.17 (3)0.06 (3)0.06 (4)0.041 (19)
O1S0.76 (10)0.24 (3)0.15 (2)0.21 (5)0.06 (4)0.11 (2)
C4S0.61 (10)0.090 (16)0.27 (5)0.09 (3)0.26 (6)0.12 (2)
Geometric parameters (Å, º) top
O1B—C3B1.367 (6)C3A—C2A1.388 (8)
O1B—H1OB0.82C11A—C1A1.401 (8)
O2B—C4B1.382 (6)C11A—C10A1.515 (8)
O2B—C5B1.464 (6)C10A—C9A1.545 (8)
O3B—C6B1.207 (7)C10A—H10C0.97
O4B—C14B1.451 (6)C10A—H10D0.97
O4B—H4OB0.82C9A—C14A1.537 (8)
O1A—C3A1.364 (6)C9A—H9A0.98
O1A—H1OA0.82C17A—C18A1.507 (10)
O2A—C4A1.384 (6)C17A—H17C0.97
O2A—C5A1.466 (6)C17A—H17D0.97
O4A—C14A1.438 (6)C18A—C20A1.467 (12)
O4A—H4OA0.82C18A—C19A1.474 (9)
O3A—C6A1.199 (8)C18A—H18A0.98
C12A—C4A1.375 (7)C19A—C20A1.469 (11)
C12A—C11A1.377 (7)C19A—H19C0.97
C12A—C13A1.501 (7)C19A—H19D0.97
N1A—C16A1.451 (7)C5A—C6A1.536 (8)
N1A—C9A1.481 (8)C5A—C13A1.537 (7)
N1A—C17A1.481 (8)C5A—H5A0.98
C19B—C20B1.471 (11)C13A—C15A1.532 (8)
C19B—C18B1.519 (11)C13A—C14A1.548 (7)
C19B—H19A0.97C1A—C2A1.367 (8)
C19B—H19B0.97C1A—H1A0.93
C18B—C17B1.443 (11)C2A—H2A0.93
C18B—C20B1.463 (12)C20A—H20C0.97
C18B—H18B0.98C20A—H20D0.97
C17B—N1B1.468 (8)C16A—C15A1.529 (8)
C17B—H17A0.97C16A—H16C0.97
C17B—H17B0.97C16A—H16D0.97
N1B—C9B1.468 (7)C15A—H15C0.97
N1B—C16B1.474 (8)C15A—H15D0.97
C9B—C14B1.529 (8)C14A—C8A1.496 (8)
C9B—C10B1.541 (8)C8A—C7A1.538 (10)
C9B—H9B0.98C8A—H8A10.97
C10B—C11B1.514 (7)C8A—H8A20.97
C10B—H10A0.97C7A—C6A1.490 (10)
C10B—H10B0.97C7A—H7A10.97
C11B—C12B1.366 (8)C7A—H7A20.97
C11B—C1B1.393 (8)C5S—C6S1.47 (3)
C12B—C4B1.388 (7)C5S—H5S10.96
C12B—C13B1.504 (7)C5S—H5S20.96
C4B—C3B1.372 (7)C5S—H5S30.96
C3B—C2B1.385 (8)C7S—O2S1.42 (2)
C5B—C6B1.521 (8)C7S—C8S1.44 (2)
C5B—C13B1.546 (7)C7S—H7S10.97
C5B—H5B0.98C7S—H7S20.97
C6B—C7B1.501 (9)O2S—C6S1.42 (2)
C7B—C8B1.523 (10)C3S—O1S1.42 (3)
C7B—H7B10.97C3S—C4S1.49 (3)
C7B—H7B20.97C3S—H3S10.97
C8B—C14B1.514 (8)C3S—H3S20.97
C8B—H8B10.97C6S—H6S10.97
C8B—H8B20.97C6S—H6S20.97
C14B—C13B1.515 (7)C1S—C2S1.49 (3)
C20B—H20A0.97C1S—H1S10.96
C20B—H20B0.97C1S—H1S20.96
C16B—C15B1.527 (8)C1S—H1S30.96
C16B—H16A0.97C2S—O1S1.40 (3)
C16B—H16B0.97C2S—H2S10.97
C15B—C13B1.543 (7)C2S—H2S20.97
C15B—H15A0.97C8S—H8S10.96
C15B—H15B0.97C8S—H8S20.96
C1B—C2B1.395 (8)C8S—H8S30.96
C1B—H1B0.93C4S—H4S10.96
C2B—H2B0.93C4S—H4S20.96
C3A—C4A1.385 (7)C4S—H4S30.96
C3B—O1B—H1OB109.5N1A—C9A—C10A116.3 (5)
C4B—O2B—C5B104.2 (4)C14A—C9A—C10A114.3 (5)
C14B—O4B—H4OB109.5N1A—C9A—H9A106.7
C3A—O1A—H1OA109.5C14A—C9A—H9A106.7
C4A—O2A—C5A104.4 (4)C10A—C9A—H9A106.7
C14A—O4A—H4OA109.5N1A—C17A—C18A112.8 (5)
C4A—C12A—C11A123.3 (5)N1A—C17A—H17C109
C4A—C12A—C13A109.2 (4)C18A—C17A—H17C109
C11A—C12A—C13A127.5 (4)N1A—C17A—H17D109
C16A—N1A—C9A112.8 (4)C18A—C17A—H17D109
C16A—N1A—C17A111.7 (5)H17C—C17A—H17D107.8
C9A—N1A—C17A113.9 (5)C20A—C18A—C19A59.9 (5)
C20B—C19B—C18B58.5 (5)C20A—C18A—C17A118.4 (8)
C20B—C19B—H19A117.9C19A—C18A—C17A117.7 (6)
C18B—C19B—H19A117.9C20A—C18A—H18A116.3
C20B—C19B—H19B117.9C19A—C18A—H18A116.3
C18B—C19B—H19B117.9C17A—C18A—H18A116.3
H19A—C19B—H19B115.1C20A—C19A—C18A59.8 (5)
C17B—C18B—C20B122.5 (9)C20A—C19A—H19C117.8
C17B—C18B—C19B119.5 (9)C18A—C19A—H19C117.8
C20B—C18B—C19B59.1 (6)C20A—C19A—H19D117.8
C17B—C18B—H18B114.8C18A—C19A—H19D117.8
C20B—C18B—H18B114.8H19C—C19A—H19D114.9
C19B—C18B—H18B114.8O2A—C5A—C6A107.6 (4)
C18B—C17B—N1B115.6 (7)O2A—C5A—C13A105.0 (4)
C18B—C17B—H17A108.4C6A—C5A—C13A114.4 (5)
N1B—C17B—H17A108.4O2A—C5A—H5A109.9
C18B—C17B—H17B108.4C6A—C5A—H5A109.9
N1B—C17B—H17B108.4C13A—C5A—H5A109.9
H17A—C17B—H17B107.4C12A—C13A—C15A110.3 (4)
C17B—N1B—C9B112.5 (5)C12A—C13A—C5A98.4 (4)
C17B—N1B—C16B113.2 (6)C15A—C13A—C5A113.1 (4)
C9B—N1B—C16B112.1 (4)C12A—C13A—C14A107.9 (4)
N1B—C9B—C14B104.4 (4)C15A—C13A—C14A108.8 (4)
N1B—C9B—C10B116.8 (5)C5A—C13A—C14A117.5 (4)
C14B—C9B—C10B114.6 (4)C2A—C1A—C11A121.6 (5)
N1B—C9B—H9B106.8C2A—C1A—H1A119.2
C14B—C9B—H9B106.8C11A—C1A—H1A119.2
C10B—C9B—H9B106.8C1A—C2A—C3A122.8 (5)
C11B—C10B—C9B114.8 (5)C1A—C2A—H2A118.6
C11B—C10B—H10A108.6C3A—C2A—H2A118.6
C9B—C10B—H10A108.6C18A—C20A—C19A60.3 (6)
C11B—C10B—H10B108.6C18A—C20A—H20C117.7
C9B—C10B—H10B108.6C19A—C20A—H20C117.7
H10A—C10B—H10B107.5C18A—C20A—H20D117.7
C12B—C11B—C1B115.7 (5)C19A—C20A—H20D117.7
C12B—C11B—C10B117.2 (5)H20C—C20A—H20D114.9
C1B—C11B—C10B127.0 (5)N1A—C16A—C15A110.9 (5)
C11B—C12B—C4B124.0 (5)N1A—C16A—H16C109.4
C11B—C12B—C13B127.5 (4)C15A—C16A—H16C109.4
C4B—C12B—C13B108.5 (4)N1A—C16A—H16D109.4
C3B—C4B—O2B127.8 (4)C15A—C16A—H16D109.4
C3B—C4B—C12B120.3 (5)H16C—C16A—H16D108
O2B—C4B—C12B111.9 (4)C16A—C15A—C13A111.8 (4)
O1B—C3B—C4B123.4 (5)C16A—C15A—H15C109.2
O1B—C3B—C2B119.7 (5)C13A—C15A—H15C109.2
C4B—C3B—C2B116.9 (5)C16A—C15A—H15D109.2
O2B—C5B—C6B108.3 (4)C13A—C15A—H15D109.2
O2B—C5B—C13B104.9 (4)H15C—C15A—H15D107.9
C6B—C5B—C13B112.0 (4)O4A—C14A—C8A106.6 (4)
O2B—C5B—H5B110.5O4A—C14A—C9A108.0 (4)
C6B—C5B—H5B110.5C8A—C14A—C9A114.1 (5)
C13B—C5B—H5B110.5O4A—C14A—C13A110.1 (4)
O3B—C6B—C7B122.5 (6)C8A—C14A—C13A111.7 (4)
O3B—C6B—C5B121.7 (6)C9A—C14A—C13A106.1 (4)
C7B—C6B—C5B115.8 (5)C14A—C8A—C7A111.0 (5)
C6B—C7B—C8B109.8 (5)C14A—C8A—H8A1109.4
C6B—C7B—H7B1109.7C7A—C8A—H8A1109.4
C8B—C7B—H7B1109.7C14A—C8A—H8A2109.4
C6B—C7B—H7B2109.7C7A—C8A—H8A2109.4
C8B—C7B—H7B2109.7H8A1—C8A—H8A2108
H7B1—C7B—H7B2108.2C6A—C7A—C8A111.9 (5)
C14B—C8B—C7B110.4 (5)C6A—C7A—H7A1109.2
C14B—C8B—H8B1109.6C8A—C7A—H7A1109.2
C7B—C8B—H8B1109.6C6A—C7A—H7A2109.2
C14B—C8B—H8B2109.6C8A—C7A—H7A2109.2
C7B—C8B—H8B2109.6H7A1—C7A—H7A2107.9
H8B1—C8B—H8B2108.1O3A—C6A—C7A124.0 (6)
O4B—C14B—C8B105.6 (5)O3A—C6A—C5A119.1 (6)
O4B—C14B—C13B110.7 (4)C7A—C6A—C5A116.9 (5)
C8B—C14B—C13B111.9 (4)C6S—C5S—H5S1109.5
O4B—C14B—C9B107.9 (4)C6S—C5S—H5S2109.5
C8B—C14B—C9B113.4 (5)H5S1—C5S—H5S2109.5
C13B—C14B—C9B107.3 (5)C6S—C5S—H5S3109.5
C18B—C20B—C19B62.3 (6)H5S1—C5S—H5S3109.5
C18B—C20B—H20A117.5H5S2—C5S—H5S3109.5
C19B—C20B—H20A117.5O2S—C7S—C8S126 (3)
C18B—C20B—H20B117.5O2S—C7S—H7S1105.7
C19B—C20B—H20B117.5C8S—C7S—H7S1105.7
H20A—C20B—H20B114.6O2S—C7S—H7S2105.7
N1B—C16B—C15B110.5 (5)C8S—C7S—H7S2105.7
N1B—C16B—H16A109.5H7S1—C7S—H7S2106.1
C15B—C16B—H16A109.5C6S—O2S—C7S122 (3)
N1B—C16B—H16B109.5O1S—C3S—C4S119 (3)
C15B—C16B—H16B109.5O1S—C3S—H3S1107.5
H16A—C16B—H16B108.1C4S—C3S—H3S1107.5
C16B—C15B—C13B110.9 (4)O1S—C3S—H3S2107.5
C16B—C15B—H15A109.5C4S—C3S—H3S2107.5
C13B—C15B—H15A109.5H3S1—C3S—H3S2107
C16B—C15B—H15B109.5O2S—C6S—C5S132 (3)
C13B—C15B—H15B109.5O2S—C6S—H6S1104.1
H15A—C15B—H15B108C5S—C6S—H6S1104.1
C12B—C13B—C14B108.7 (4)O2S—C6S—H6S2104.1
C12B—C13B—C15B109.0 (5)C5S—C6S—H6S2104.1
C14B—C13B—C15B109.0 (4)H6S1—C6S—H6S2105.5
C12B—C13B—C5B98.0 (4)C2S—C1S—H1S1109.5
C14B—C13B—C5B118.6 (5)C2S—C1S—H1S2109.5
C15B—C13B—C5B112.6 (4)H1S1—C1S—H1S2109.5
C11B—C1B—C2B120.8 (5)C2S—C1S—H1S3109.5
C11B—C1B—H1B119.6H1S1—C1S—H1S3109.5
C2B—C1B—H1B119.6H1S2—C1S—H1S3109.5
C3B—C2B—C1B122.1 (5)O1S—C2S—C1S139 (4)
C3B—C2B—H2B118.9O1S—C2S—H2S1102.4
C1B—C2B—H2B118.9C1S—C2S—H2S1102.4
O1A—C3A—C4A123.8 (5)O1S—C2S—H2S2102.4
O1A—C3A—C2A120.5 (5)C1S—C2S—H2S2102.4
C4A—C3A—C2A115.7 (5)H2S1—C2S—H2S2104.9
C12A—C4A—O2A111.6 (4)C7S—C8S—H8S1109.5
C12A—C4A—C3A121.3 (4)C7S—C8S—H8S2109.5
O2A—C4A—C3A127.0 (5)H8S1—C8S—H8S2109.5
C12A—C11A—C1A115.1 (5)C7S—C8S—H8S3109.5
C12A—C11A—C10A117.3 (5)H8S1—C8S—H8S3109.5
C1A—C11A—C10A127.3 (5)H8S2—C8S—H8S3109.5
C11A—C10A—C9A114.8 (4)C2S—O1S—C3S110 (3)
C11A—C10A—H10C108.6C3S—C4S—H4S1109.5
C9A—C10A—H10C108.6C3S—C4S—H4S2109.5
C11A—C10A—H10D108.6H4S1—C4S—H4S2109.5
C9A—C10A—H10D108.6C3S—C4S—H4S3109.5
H10C—C10A—H10D107.5H4S1—C4S—H4S3109.5
N1A—C9A—C14A105.4 (4)H4S2—C4S—H4S3109.5
C20B—C19B—C18B—C17B112.3 (10)C11A—C12A—C4A—C3A3.6 (8)
C20B—C18B—C17B—N1B74.3 (11)C13A—C12A—C4A—C3A178.0 (5)
N1B—C17B—C18B—C19B144.5 (8)C5A—O2A—C4A—C12A18.4 (5)
C9B—N1B—C17B—C18B160.0 (7)C5A—O2A—C4A—C3A160.4 (5)
C18B—C17B—N1B—C16B71.6 (8)O1A—C3A—C4A—C12A179.9 (5)
C17B—N1B—C9B—C14B163.3 (5)C2A—C3A—C4A—C12A0.9 (7)
C16B—N1B—C9B—C14B67.8 (6)O1A—C3A—C4A—O2A1.4 (8)
C17B—N1B—C9B—C10B69.1 (6)C2A—C3A—C4A—O2A177.8 (5)
C16B—N1B—C9B—C10B59.9 (6)C4A—C12A—C11A—C1A3.6 (8)
N1B—C9B—C10B—C11B88.3 (7)C13A—C12A—C11A—C1A178.3 (5)
C14B—C9B—C10B—C11B34.2 (8)C4A—C12A—C11A—C10A171.3 (5)
C9B—C10B—C11B—C12B6.2 (9)C13A—C12A—C11A—C10A6.8 (8)
C9B—C10B—C11B—C1B177.8 (6)C12A—C11A—C10A—C9A5.9 (8)
C1B—C11B—C12B—C4B3.0 (9)C1A—C11A—C10A—C9A179.9 (6)
C10B—C11B—C12B—C4B173.5 (6)C16A—N1A—C9A—C14A67.0 (6)
C1B—C11B—C12B—C13B177.2 (5)C17A—N1A—C9A—C14A164.4 (5)
C10B—C11B—C12B—C13B6.3 (9)C16A—N1A—C9A—C10A60.8 (6)
C5B—O2B—C4B—C3B161.0 (6)C17A—N1A—C9A—C10A67.8 (6)
C5B—O2B—C4B—C12B18.3 (6)C11A—C10A—C9A—N1A88.3 (6)
C11B—C12B—C4B—C3B3.9 (9)C11A—C10A—C9A—C14A34.9 (8)
C13B—C12B—C4B—C3B176.2 (5)C16A—N1A—C17A—C18A77.9 (7)
C11B—C12B—C4B—O2B175.5 (5)C9A—N1A—C17A—C18A152.9 (6)
C13B—C12B—C4B—O2B4.4 (6)N1A—C17A—C18A—C20A83.8 (8)
O2B—C4B—C3B—O1B2.6 (9)N1A—C17A—C18A—C19A152.8 (7)
C12B—C4B—C3B—O1B178.1 (5)C17A—C18A—C19A—C20A108.4 (9)
O2B—C4B—C3B—C2B178.0 (5)C4A—O2A—C5A—C6A90.3 (5)
C12B—C4B—C3B—C2B1.3 (8)C4A—O2A—C5A—C13A32.0 (5)
C4B—O2B—C5B—C6B86.7 (5)C4A—C12A—C13A—C15A96.9 (5)
C4B—O2B—C5B—C13B33.0 (5)C11A—C12A—C13A—C15A84.8 (6)
O2B—C5B—C6B—O3B22.4 (8)C4A—C12A—C13A—C5A21.7 (5)
C13B—C5B—C6B—O3B137.5 (6)C11A—C12A—C13A—C5A156.6 (5)
O2B—C5B—C6B—C7B155.6 (5)C4A—C12A—C13A—C14A144.3 (4)
C13B—C5B—C6B—C7B40.4 (7)C11A—C12A—C13A—C14A34.0 (7)
O3B—C6B—C7B—C8B121.9 (7)O2A—C5A—C13A—C12A32.0 (5)
C5B—C6B—C7B—C8B56.0 (7)C6A—C5A—C13A—C12A85.8 (5)
C6B—C7B—C8B—C14B62.2 (6)O2A—C5A—C13A—C15A84.5 (5)
C7B—C8B—C14B—O4B65.9 (5)C6A—C5A—C13A—C15A157.8 (5)
C7B—C8B—C14B—C13B54.6 (6)O2A—C5A—C13A—C14A147.3 (4)
C7B—C8B—C14B—C9B176.1 (4)C6A—C5A—C13A—C14A29.5 (6)
N1B—C9B—C14B—O4B50.1 (5)C12A—C11A—C1A—C2A1.3 (9)
C10B—C9B—C14B—O4B179.1 (5)C10A—C11A—C1A—C2A173.0 (6)
N1B—C9B—C14B—C8B166.8 (4)C11A—C1A—C2A—C3A1.2 (10)
C10B—C9B—C14B—C8B64.3 (6)O1A—C3A—C2A—C1A177.8 (5)
N1B—C9B—C14B—C13B69.1 (5)C4A—C3A—C2A—C1A1.3 (8)
C10B—C9B—C14B—C13B59.9 (6)C17A—C18A—C20A—C19A107.4 (7)
C17B—C18B—C20B—C19B107.4 (10)C9A—N1A—C16A—C15A57.4 (6)
C17B—N1B—C16B—C15B172.5 (5)C17A—N1A—C16A—C15A172.9 (5)
C9B—N1B—C16B—C15B58.9 (6)N1A—C16A—C15A—C13A49.6 (6)
N1B—C16B—C15B—C13B49.5 (6)C12A—C13A—C15A—C16A64.8 (6)
C11B—C12B—C13B—C14B32.5 (8)C5A—C13A—C15A—C16A174.0 (4)
C4B—C12B—C13B—C14B147.3 (5)C14A—C13A—C15A—C16A53.4 (6)
C11B—C12B—C13B—C15B86.2 (7)N1A—C9A—C14A—O4A50.4 (5)
C4B—C12B—C13B—C15B94.0 (5)C10A—C9A—C14A—O4A179.4 (5)
C11B—C12B—C13B—C5B156.5 (6)N1A—C9A—C14A—C8A168.8 (4)
C4B—C12B—C13B—C5B23.4 (5)C10A—C9A—C14A—C8A62.3 (7)
O4B—C14B—C13B—C12B172.9 (4)N1A—C9A—C14A—C13A67.7 (5)
C8B—C14B—C13B—C12B69.6 (6)C10A—C9A—C14A—C13A61.3 (6)
C9B—C14B—C13B—C12B55.4 (5)C12A—C13A—C14A—O4A173.8 (4)
O4B—C14B—C13B—C15B54.2 (6)C15A—C13A—C14A—O4A54.1 (5)
C8B—C14B—C13B—C15B171.8 (5)C5A—C13A—C14A—O4A76.2 (6)
C9B—C14B—C13B—C15B63.2 (5)C12A—C13A—C14A—C8A67.9 (5)
O4B—C14B—C13B—C5B76.4 (5)C15A—C13A—C14A—C8A172.4 (5)
C8B—C14B—C13B—C5B41.1 (6)C5A—C13A—C14A—C8A42.1 (6)
C9B—C14B—C13B—C5B166.1 (4)C12A—C13A—C14A—C9A57.1 (5)
C16B—C15B—C13B—C12B65.5 (5)C15A—C13A—C14A—C9A62.6 (5)
C16B—C15B—C13B—C14B53.0 (6)C5A—C13A—C14A—C9A167.1 (4)
C16B—C15B—C13B—C5B173.1 (4)O4A—C14A—C8A—C7A64.4 (6)
O2B—C5B—C13B—C12B33.8 (5)C9A—C14A—C8A—C7A176.4 (5)
C6B—C5B—C13B—C12B83.5 (5)C13A—C14A—C8A—C7A56.0 (6)
O2B—C5B—C13B—C14B150.2 (4)C14A—C8A—C7A—C6A59.8 (7)
C6B—C5B—C13B—C14B33.0 (6)C8A—C7A—C6A—O3A131.0 (7)
O2B—C5B—C13B—C15B80.8 (5)C8A—C7A—C6A—C5A47.8 (7)
C6B—C5B—C13B—C15B162.0 (4)O2A—C5A—C6A—O3A29.9 (7)
C12B—C11B—C1B—C2B0.3 (9)C13A—C5A—C6A—O3A146.1 (6)
C10B—C11B—C1B—C2B176.4 (6)O2A—C5A—C6A—C7A149.1 (5)
O1B—C3B—C2B—C1B178.6 (6)C13A—C5A—C6A—C7A32.8 (7)
C4B—C3B—C2B—C1B1.9 (9)C8S—C7S—O2S—C6S161 (3)
C11B—C1B—C2B—C3B2.8 (10)C7S—O2S—C6S—C5S161 (4)
C11A—C12A—C4A—O2A175.3 (5)C1S—C2S—O1S—C3S175 (4)
C13A—C12A—C4A—O2A3.1 (6)C4S—C3S—O1S—C2S165 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1OA···O4Ai0.821.932.737 (5)167
O4A—H4OA···O2Aii0.822.562.982 (6)114
O1B—H1OB···O4Biii0.821.932.730 (6)166
O4B—H4OB···O2Biv0.822.513.000 (5)120
C20B—H20A···O4Av0.972.713.560 (11)146
C20B—H20B···O1Bvi0.972.643.533 (10)154
Symmetry codes: (i) x+2, y1/2, z+3/2; (ii) x+2, y+1/2, z+3/2; (iii) x1/2, y+3/2, z; (iv) x+1/2, y+3/2, z; (v) x+2, y1/2, z+1/2; (vi) x+1, y, z.
 

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