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
CCDC references: 1820437; 1820436
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).
(4
R,4a
S,7a
R,12b
S)-3-Cyclopropylmethyl-4a,9-dihydroxy-2,4,5,6,7a,13-hexahydro-1
H-4,12-methanobenzofuro[3,2-
e]isoquinolin-7-one ethyl acetate 0.33-solvate (naltrexone_AcOEt)
top
Crystal data top
3C20H23NO4·C4H8O2 | Dx = 1.282 Mg m−3 |
Mr = 1112.29 | Cu Kα radiation, λ = 1.54178 Å |
Orthorhombic, P212121 | Cell parameters from 2253 reflections |
a = 13.0034 (4) Å | θ = 4.2–52.1° |
b = 14.0829 (4) Å | µ = 0.73 mm−1 |
c = 31.479 (1) Å | T = 296 K |
V = 5764.6 (3) Å3 | Prism, colourless |
Z = 4 | 0.22 × 0.18 × 0.10 mm |
F(000) = 2376 | |
Data collection top
Bruker APEXII CCD diffractometer | 7082 reflections with I > 2σ(I) |
CCD scans | Rint = 0.034 |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | θmax = 66.6°, θmin = 2.8° |
Tmin = 0.793, Tmax = 0.929 | h = −15→15 |
20908 measured reflections | k = −16→13 |
9344 independent reflections | l = −36→32 |
Refinement top
Refinement on F2 | Hydrogen site location: constr |
Least-squares matrix: full | H-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 = 1.01 | Δρmax = 0.30 e Å−3 |
9344 reflections | Δρmin = −0.23 e Å−3 |
756 parameters | Absolute structure: Flack x determined using 2489 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
1 restraint | Absolute 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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
C19B | 0.2678 (6) | 0.1762 (8) | 0.8426 (3) | 0.142 (3) | |
H19A | 0.281 | 0.2117 | 0.8167 | 0.17* | 0.737 (19) |
H19B | 0.2275 | 0.1188 | 0.8388 | 0.17* | 0.737 (19) |
H19' | 0.1986 | 0.195 | 0.8347 | 0.17* | 0.264 (19) |
H19" | 0.3116 | 0.1564 | 0.8192 | 0.17* | 0.264 (19) |
O1A | 0.2025 (2) | 0.7568 (3) | 0.93957 (12) | 0.0812 (11) | |
H1OA | 0.1895 | 0.716 | 0.9574 | 0.122* | |
O2A | 0.0051 (2) | 0.7342 (2) | 0.98561 (10) | 0.0608 (8) | |
O4A | −0.3103 (2) | 0.8762 (2) | 0.99844 (9) | 0.0553 (7) | |
H4OA | −0.3486 | 0.8462 | 0.9827 | 0.083* | |
O3A | 0.0254 (3) | 0.8428 (3) | 1.05550 (13) | 0.0871 (11) | |
O1C | 0.6456 (3) | 0.4318 (3) | 0.76068 (15) | 0.0893 (12) | |
H1OC | 0.5869 | 0.4246 | 0.7696 | 0.134* | |
O2C | 0.5389 (2) | 0.2450 (2) | 0.76809 (10) | 0.0683 (8) | |
O3C | 0.3814 (3) | 0.2488 (4) | 0.71285 (15) | 0.1202 (17) | |
O4C | 0.5455 (3) | −0.0538 (2) | 0.70877 (12) | 0.0725 (9) | |
H4OC | 0.5839 | −0.0902 | 0.7215 | 0.109* | |
O1B | 1.0266 (2) | 0.1769 (3) | 0.94123 (12) | 0.0721 (9) | |
H1OB | 1.0189 | 0.1673 | 0.9667 | 0.108* | |
O2B | 0.8399 (2) | 0.2305 (2) | 0.99131 (9) | 0.0574 (7) | |
O4B | 0.5216 (2) | 0.3676 (2) | 0.97445 (11) | 0.0615 (8) | |
H4OB | 0.4776 | 0.3299 | 0.9664 | 0.092* | |
C13A | −0.1511 (3) | 0.8133 (2) | 0.96721 (13) | 0.0433 (8) | |
N1A | −0.3210 (3) | 0.8650 (3) | 0.91451 (11) | 0.0549 (9) | |
O3B | 0.8752 (3) | 0.4114 (3) | 1.01275 (15) | 0.0932 (12) | |
C3B | 0.9370 (3) | 0.2094 (3) | 0.92437 (15) | 0.0544 (10) | |
C4B | 0.8505 (3) | 0.2325 (3) | 0.94734 (14) | 0.0520 (10) | |
O2S | 0.9737 (5) | 0.5073 (5) | 0.8661 (2) | 0.154 (2) | |
C3A | 0.1145 (3) | 0.8063 (4) | 0.93004 (15) | 0.0607 (11) | |
C4A | 0.0226 (3) | 0.7927 (3) | 0.95091 (14) | 0.0526 (10) | |
C12A | −0.0630 (3) | 0.8430 (3) | 0.93933 (13) | 0.0485 (9) | |
C15A | −0.2167 (3) | 0.7368 (3) | 0.94539 (14) | 0.0512 (9) | |
H15A | −0.1735 | 0.6833 | 0.9377 | 0.061* | |
H15B | −0.269 | 0.7143 | 0.965 | 0.061* | |
C16A | −0.2678 (3) | 0.7760 (3) | 0.90588 (14) | 0.0575 (11) | |
H16A | −0.2161 | 0.7864 | 0.8842 | 0.069* | |
H16B | −0.3167 | 0.7299 | 0.8951 | 0.069* | |
C17A | −0.3821 (4) | 0.8986 (4) | 0.87857 (16) | 0.0725 (14) | |
H17A | −0.3466 | 0.8833 | 0.8524 | 0.087* | |
H17B | −0.3883 | 0.9672 | 0.8802 | 0.087* | |
C18A | −0.4869 (5) | 0.8560 (6) | 0.8775 (2) | 0.099 (2) | |
H18A | −0.4896 | 0.7869 | 0.874 | 0.118* | |
C20A | −0.5681 (5) | 0.8971 (5) | 0.9023 (2) | 0.0923 (18) | |
H20A | −0.5514 | 0.9519 | 0.9197 | 0.111* | |
H20B | −0.6183 | 0.8543 | 0.9147 | 0.111* | |
C5A | −0.0878 (3) | 0.7736 (3) | 1.00491 (13) | 0.0498 (10) | |
H5A | −0.1265 | 0.7231 | 1.0191 | 0.06* | |
C19A | −0.5703 (4) | 0.9101 (6) | 0.8565 (2) | 0.100 (2) | |
H19C | −0.5541 | 0.9725 | 0.8454 | 0.12* | |
H19D | −0.6211 | 0.8748 | 0.8404 | 0.12* | |
C9A | −0.2510 (3) | 0.9383 (3) | 0.93151 (13) | 0.0502 (9) | |
H9A | −0.2928 | 0.9952 | 0.9364 | 0.06* | |
C10A | −0.1607 (4) | 0.9689 (3) | 0.90250 (16) | 0.0626 (12) | |
H10A | −0.1822 | 0.9628 | 0.8731 | 0.075* | |
H10B | −0.1459 | 1.0354 | 0.9077 | 0.075* | |
C11A | −0.0634 (3) | 0.9128 (3) | 0.90868 (14) | 0.0552 (10) | |
C1A | 0.0303 (4) | 0.9277 (4) | 0.88838 (16) | 0.0671 (12) | |
H1A | 0.0352 | 0.9743 | 0.8675 | 0.081* | |
C2A | 0.1160 (4) | 0.8751 (4) | 0.89854 (16) | 0.0724 (14) | |
H2A | 0.1769 | 0.886 | 0.8838 | 0.087* | |
C14A | −0.2181 (3) | 0.9013 (3) | 0.97572 (13) | 0.0474 (9) | |
C8A | −0.1625 (3) | 0.9739 (3) | 1.00238 (14) | 0.0561 (10) | |
H8A1 | −0.2077 | 1.0273 | 1.008 | 0.067* | |
H8A2 | −0.1029 | 0.9973 | 0.987 | 0.067* | |
C7A | −0.1281 (4) | 0.9296 (3) | 1.04439 (15) | 0.0613 (11) | |
H7A1 | −0.0941 | 0.9774 | 1.0616 | 0.074* | |
H7A2 | −0.1879 | 0.9074 | 1.0599 | 0.074* | |
C6A | −0.0567 (3) | 0.8489 (3) | 1.03714 (15) | 0.0583 (11) | |
C3C | 0.6808 (4) | 0.3474 (3) | 0.74384 (16) | 0.0666 (12) | |
C4C | 0.6321 (3) | 0.2625 (3) | 0.74720 (14) | 0.0584 (11) | |
C12C | 0.6687 (3) | 0.1829 (3) | 0.72790 (13) | 0.0546 (10) | |
C11C | 0.7550 (4) | 0.1825 (3) | 0.70277 (14) | 0.0616 (11) | |
C10C | 0.7785 (4) | 0.0947 (4) | 0.67797 (17) | 0.0753 (14) | |
H10C | 0.8499 | 0.0778 | 0.6826 | 0.09* | |
H10D | 0.77 | 0.1084 | 0.648 | 0.09* | |
C9C | 0.7108 (4) | 0.0093 (4) | 0.68949 (15) | 0.0667 (13) | |
H9C | 0.7091 | −0.0317 | 0.6643 | 0.08* | |
N1C | 0.7455 (3) | −0.0510 (3) | 0.72529 (13) | 0.0687 (10) | |
C17C | 0.8397 (4) | −0.1039 (4) | 0.7160 (2) | 0.0844 (16) | |
H17C | 0.8978 | −0.0608 | 0.7173 | 0.101* | |
H17D | 0.8358 | −0.1288 | 0.6873 | 0.101* | |
C18C | 0.8575 (4) | −0.1833 (5) | 0.7458 (2) | 0.0902 (17) | |
H18C | 0.7987 | −0.2254 | 0.7509 | 0.108* | |
C5C | 0.5031 (3) | 0.1548 (3) | 0.75016 (15) | 0.0590 (11) | |
H5C | 0.4643 | 0.1196 | 0.7717 | 0.071* | |
C6C | 0.4331 (4) | 0.1769 (4) | 0.71210 (18) | 0.0739 (14) | |
C7C | 0.4324 (4) | 0.1082 (4) | 0.67640 (19) | 0.0788 (15) | |
H7C1 | 0.397 | 0.1362 | 0.6523 | 0.095* | |
H7C2 | 0.3948 | 0.0518 | 0.6848 | 0.095* | |
C8C | 0.5409 (4) | 0.0804 (4) | 0.66312 (16) | 0.0722 (14) | |
H8C1 | 0.5779 | 0.1364 | 0.6538 | 0.087* | |
H8C2 | 0.5374 | 0.0365 | 0.6394 | 0.087* | |
C14C | 0.5989 (4) | 0.0338 (3) | 0.69998 (15) | 0.0600 (11) | |
C13C | 0.6021 (3) | 0.0998 (3) | 0.73867 (13) | 0.0537 (10) | |
C15C | 0.6466 (4) | 0.0453 (4) | 0.77683 (15) | 0.0645 (12) | |
H15C | 0.6553 | 0.0884 | 0.8006 | 0.077* | |
H15D | 0.599 | −0.0042 | 0.7853 | 0.077* | |
C16C | 0.7497 (4) | 0.0012 (4) | 0.76547 (15) | 0.0716 (13) | |
H16C | 0.8011 | 0.0509 | 0.7633 | 0.086* | |
H16D | 0.7706 | −0.0417 | 0.788 | 0.086* | |
C1C | 0.8063 (4) | 0.2696 (4) | 0.69948 (17) | 0.0728 (14) | |
H1C | 0.8654 | 0.2737 | 0.683 | 0.087* | |
C2C | 0.7713 (4) | 0.3484 (4) | 0.72000 (18) | 0.0749 (14) | |
H2C | 0.8087 | 0.4045 | 0.7181 | 0.09* | |
O1S | 0.8152 (6) | 0.5506 (6) | 0.8733 (3) | 0.195 (3) | |
C3S | 0.8890 (7) | 0.5358 (7) | 0.8508 (4) | 0.134 (3) | |
C12B | 0.7620 (3) | 0.2642 (3) | 0.92768 (13) | 0.0501 (9) | |
C11B | 0.7538 (4) | 0.2797 (3) | 0.88508 (15) | 0.0627 (11) | |
C10B | 0.6571 (4) | 0.3260 (4) | 0.86809 (16) | 0.0741 (14) | |
H10E | 0.6307 | 0.2882 | 0.8447 | 0.089* | |
H10F | 0.6743 | 0.3883 | 0.857 | 0.089* | |
C9B | 0.5720 (3) | 0.3368 (4) | 0.90204 (16) | 0.0645 (12) | |
H9B | 0.5288 | 0.3902 | 0.8931 | 0.077* | |
N1B | 0.5027 (3) | 0.2541 (3) | 0.90770 (12) | 0.0664 (10) | |
C17B | 0.4412 (4) | 0.2335 (6) | 0.86913 (18) | 0.097 (2) | |
H17E | 0.4204 | 0.2933 | 0.8565 | 0.116* | |
H17F | 0.4849 | 0.2011 | 0.8488 | 0.116* | |
C2B | 0.9294 (4) | 0.2221 (4) | 0.88102 (16) | 0.0667 (12) | |
H2B | 0.9859 | 0.2069 | 0.8643 | 0.08* | |
C1B | 0.8415 (4) | 0.2565 (4) | 0.86108 (16) | 0.0719 (13) | |
H1B | 0.8407 | 0.2643 | 0.8317 | 0.086* | |
C13B | 0.6788 (3) | 0.2771 (3) | 0.96057 (13) | 0.0486 (9) | |
C5B | 0.7505 (3) | 0.2913 (3) | 0.99952 (14) | 0.0528 (10) | |
H5B | 0.7155 | 0.2705 | 1.0255 | 0.063* | |
C6B | 0.7875 (4) | 0.3936 (3) | 1.00463 (16) | 0.0639 (12) | |
C7B | 0.7086 (4) | 0.4689 (3) | 0.9956 (2) | 0.0754 (15) | |
H7B1 | 0.7399 | 0.5313 | 0.9979 | 0.09* | |
H7B2 | 0.6533 | 0.4649 | 1.0162 | 0.09* | |
C8B | 0.6659 (4) | 0.4547 (3) | 0.95070 (18) | 0.0689 (14) | |
H8B1 | 0.6185 | 0.5057 | 0.944 | 0.083* | |
H8B2 | 0.7218 | 0.4568 | 0.9303 | 0.083* | |
C14B | 0.6109 (3) | 0.3605 (3) | 0.94730 (15) | 0.0549 (11) | |
C16B | 0.5579 (4) | 0.1688 (3) | 0.92226 (15) | 0.0622 (11) | |
H16E | 0.6074 | 0.1497 | 0.9008 | 0.075* | |
H16F | 0.5094 | 0.1172 | 0.9261 | 0.075* | |
C15B | 0.6131 (3) | 0.1876 (3) | 0.96354 (14) | 0.0526 (10) | |
H15E | 0.6565 | 0.1338 | 0.9704 | 0.063* | |
H15F | 0.563 | 0.195 | 0.9862 | 0.063* | |
C18B | 0.3494 (9) | 0.1758 (11) | 0.8761 (3) | 0.096 (4) | 0.737 (19) |
H18B | 0.3574 | 0.1177 | 0.8929 | 0.115* | 0.737 (19) |
C20C | 0.9296 (6) | −0.1704 (8) | 0.7824 (3) | 0.143 (3) | |
H20C | 0.9136 | −0.2028 | 0.8088 | 0.171* | |
H20D | 0.9623 | −0.1089 | 0.7858 | 0.171* | |
C19C | 0.9607 (5) | −0.2300 (6) | 0.7450 (3) | 0.123 (3) | |
H19E | 1.0121 | −0.2044 | 0.7258 | 0.148* | |
H19F | 0.9634 | −0.2983 | 0.7488 | 0.148* | |
C20B | 0.2542 (11) | 0.2284 (13) | 0.8810 (3) | 0.132 (6) | 0.737 (19) |
H20E | 0.2044 | 0.2044 | 0.9013 | 0.159* | 0.737 (19) |
H20F | 0.2578 | 0.2971 | 0.8793 | 0.159* | 0.737 (19) |
C1S | 1.0791 (8) | 0.4552 (8) | 0.9214 (3) | 0.167 (4) | |
H1S1 | 1.0882 | 0.4551 | 0.9516 | 0.25* | |
H1S2 | 1.073 | 0.391 | 0.9114 | 0.25* | |
H1S3 | 1.1374 | 0.4849 | 0.9082 | 0.25* | |
C2S | 0.9886 (11) | 0.5064 (9) | 0.9109 (3) | 0.189 (6) | |
H2S1 | 0.9943 | 0.571 | 0.9213 | 0.227* | |
H2S2 | 0.9298 | 0.477 | 0.9245 | 0.227* | |
C4S | 0.8745 (8) | 0.5306 (11) | 0.8066 (3) | 0.199 (6) | |
H4S1 | 0.9393 | 0.5186 | 0.793 | 0.298* | |
H4S2 | 0.8275 | 0.48 | 0.8001 | 0.298* | |
H4S3 | 0.8468 | 0.5896 | 0.7965 | 0.298* | |
C18' | 0.322 (2) | 0.229 (2) | 0.8825 (9) | 0.072 (8) | 0.264 (19) |
H18' | 0.2879 | 0.2814 | 0.8977 | 0.086* | 0.264 (19) |
C20' | 0.279 (2) | 0.128 (2) | 0.8834 (8) | 0.091 (10) | 0.264 (19) |
H20G | 0.3288 | 0.0763 | 0.8848 | 0.109* | 0.264 (19) |
H20H | 0.2171 | 0.1166 | 0.8997 | 0.109* | 0.264 (19) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C19B | 0.089 (5) | 0.231 (10) | 0.106 (6) | −0.028 (6) | −0.037 (5) | 0.010 (7) |
O1A | 0.0384 (16) | 0.123 (3) | 0.082 (2) | 0.0106 (18) | 0.0099 (16) | 0.024 (2) |
O2A | 0.0372 (14) | 0.0721 (17) | 0.073 (2) | 0.0105 (13) | 0.0087 (14) | 0.0224 (16) |
O4A | 0.0353 (14) | 0.0659 (17) | 0.0647 (18) | −0.0005 (12) | −0.0001 (13) | −0.0081 (15) |
O3A | 0.066 (2) | 0.094 (2) | 0.101 (3) | −0.0097 (19) | −0.042 (2) | 0.013 (2) |
O1C | 0.090 (3) | 0.077 (2) | 0.101 (3) | −0.014 (2) | 0.010 (2) | −0.020 (2) |
O2C | 0.0618 (19) | 0.0739 (19) | 0.069 (2) | 0.0022 (16) | 0.0188 (16) | 0.0022 (17) |
O3C | 0.102 (3) | 0.149 (4) | 0.110 (3) | 0.061 (3) | 0.002 (3) | 0.024 (3) |
O4C | 0.073 (2) | 0.0601 (18) | 0.085 (2) | −0.0041 (16) | −0.0078 (19) | 0.0161 (17) |
O1B | 0.0467 (17) | 0.084 (2) | 0.086 (2) | 0.0119 (16) | 0.0080 (17) | −0.005 (2) |
O2B | 0.0511 (16) | 0.0654 (16) | 0.0556 (18) | 0.0155 (14) | 0.0000 (14) | 0.0011 (14) |
O4B | 0.0425 (15) | 0.0562 (17) | 0.086 (2) | 0.0093 (12) | 0.0102 (16) | 0.0051 (16) |
C13A | 0.0342 (19) | 0.0417 (18) | 0.054 (2) | −0.0012 (15) | 0.0007 (17) | 0.0013 (17) |
N1A | 0.0459 (19) | 0.063 (2) | 0.056 (2) | −0.0008 (16) | −0.0147 (16) | −0.0043 (17) |
O3B | 0.067 (2) | 0.091 (2) | 0.121 (3) | −0.0063 (19) | −0.021 (2) | −0.015 (2) |
C3B | 0.043 (2) | 0.054 (2) | 0.067 (3) | 0.0023 (17) | 0.007 (2) | −0.004 (2) |
C4B | 0.049 (2) | 0.049 (2) | 0.058 (3) | 0.0092 (18) | 0.003 (2) | 0.0006 (19) |
O2S | 0.104 (4) | 0.212 (7) | 0.145 (6) | 0.007 (5) | 0.005 (4) | −0.006 (5) |
C3A | 0.039 (2) | 0.084 (3) | 0.059 (3) | 0.000 (2) | 0.001 (2) | 0.003 (2) |
C4A | 0.042 (2) | 0.064 (2) | 0.052 (2) | −0.0007 (18) | 0.0036 (19) | 0.004 (2) |
C12A | 0.040 (2) | 0.056 (2) | 0.049 (2) | −0.0081 (17) | −0.0002 (18) | 0.0049 (19) |
C15A | 0.043 (2) | 0.046 (2) | 0.064 (3) | −0.0038 (16) | 0.0008 (19) | −0.0048 (19) |
C16A | 0.051 (2) | 0.059 (2) | 0.063 (3) | −0.0089 (19) | −0.008 (2) | −0.016 (2) |
C17A | 0.058 (3) | 0.096 (4) | 0.064 (3) | 0.002 (3) | −0.018 (2) | 0.002 (3) |
C18A | 0.067 (4) | 0.135 (5) | 0.094 (4) | 0.008 (4) | −0.027 (3) | −0.015 (4) |
C20A | 0.081 (4) | 0.112 (5) | 0.084 (4) | 0.015 (3) | 0.000 (3) | 0.021 (4) |
C5A | 0.0342 (19) | 0.059 (2) | 0.057 (2) | −0.0001 (17) | 0.0021 (18) | 0.012 (2) |
C19A | 0.068 (4) | 0.147 (6) | 0.086 (4) | 0.006 (4) | −0.031 (3) | 0.014 (4) |
C9A | 0.044 (2) | 0.049 (2) | 0.058 (2) | 0.0010 (17) | −0.007 (2) | −0.0014 (18) |
C10A | 0.058 (3) | 0.060 (2) | 0.069 (3) | −0.004 (2) | −0.012 (2) | 0.015 (2) |
C11A | 0.051 (2) | 0.062 (2) | 0.052 (2) | −0.0102 (19) | −0.005 (2) | 0.008 (2) |
C1A | 0.057 (3) | 0.088 (3) | 0.056 (3) | −0.013 (2) | −0.001 (2) | 0.013 (2) |
C2A | 0.051 (3) | 0.108 (4) | 0.058 (3) | −0.012 (3) | 0.011 (2) | 0.012 (3) |
C14A | 0.038 (2) | 0.048 (2) | 0.056 (2) | −0.0027 (16) | −0.0030 (18) | −0.0032 (18) |
C8A | 0.054 (2) | 0.052 (2) | 0.062 (3) | −0.0022 (19) | −0.007 (2) | −0.009 (2) |
C7A | 0.052 (2) | 0.077 (3) | 0.055 (3) | −0.011 (2) | −0.006 (2) | −0.010 (2) |
C6A | 0.043 (2) | 0.071 (3) | 0.060 (3) | −0.0152 (19) | −0.011 (2) | 0.017 (2) |
C3C | 0.065 (3) | 0.073 (3) | 0.062 (3) | −0.007 (2) | −0.004 (2) | −0.009 (2) |
C4C | 0.050 (2) | 0.075 (3) | 0.050 (2) | −0.005 (2) | 0.004 (2) | 0.002 (2) |
C12C | 0.050 (2) | 0.070 (3) | 0.044 (2) | −0.007 (2) | 0.004 (2) | 0.000 (2) |
C11C | 0.053 (3) | 0.079 (3) | 0.053 (3) | −0.006 (2) | 0.010 (2) | 0.003 (2) |
C10C | 0.073 (3) | 0.087 (3) | 0.066 (3) | 0.002 (3) | 0.022 (3) | −0.002 (3) |
C9C | 0.073 (3) | 0.078 (3) | 0.049 (3) | 0.001 (2) | 0.012 (2) | −0.003 (2) |
N1C | 0.062 (2) | 0.078 (2) | 0.066 (2) | 0.012 (2) | 0.011 (2) | 0.005 (2) |
C17C | 0.071 (3) | 0.087 (3) | 0.095 (4) | 0.011 (3) | 0.015 (3) | 0.001 (3) |
C18C | 0.063 (3) | 0.104 (4) | 0.104 (4) | 0.022 (3) | 0.000 (3) | 0.003 (4) |
C5C | 0.050 (2) | 0.066 (3) | 0.060 (3) | 0.000 (2) | 0.008 (2) | 0.013 (2) |
C6C | 0.052 (3) | 0.087 (3) | 0.083 (4) | 0.002 (3) | 0.006 (3) | 0.025 (3) |
C7C | 0.078 (3) | 0.073 (3) | 0.085 (4) | −0.014 (3) | −0.027 (3) | 0.026 (3) |
C8C | 0.096 (4) | 0.068 (3) | 0.053 (3) | −0.009 (3) | −0.014 (3) | 0.004 (2) |
C14C | 0.065 (3) | 0.060 (3) | 0.055 (3) | 0.000 (2) | 0.000 (2) | 0.005 (2) |
C13C | 0.050 (2) | 0.070 (3) | 0.041 (2) | 0.001 (2) | 0.0041 (19) | 0.005 (2) |
C15C | 0.055 (3) | 0.089 (3) | 0.049 (3) | 0.011 (2) | 0.006 (2) | 0.010 (2) |
C16C | 0.062 (3) | 0.096 (3) | 0.056 (3) | 0.016 (3) | 0.001 (3) | 0.005 (3) |
C1C | 0.053 (3) | 0.092 (4) | 0.073 (3) | −0.014 (3) | 0.010 (2) | 0.003 (3) |
C2C | 0.060 (3) | 0.082 (3) | 0.083 (4) | −0.022 (3) | −0.004 (3) | −0.001 (3) |
O1S | 0.146 (6) | 0.215 (7) | 0.222 (8) | 0.021 (6) | 0.019 (6) | −0.047 (7) |
C3S | 0.096 (6) | 0.152 (7) | 0.153 (9) | 0.030 (5) | 0.052 (6) | 0.001 (6) |
C12B | 0.046 (2) | 0.052 (2) | 0.052 (2) | 0.0058 (18) | 0.0089 (19) | 0.0028 (19) |
C11B | 0.052 (2) | 0.075 (3) | 0.061 (3) | 0.002 (2) | 0.003 (2) | 0.012 (2) |
C10B | 0.063 (3) | 0.096 (3) | 0.063 (3) | 0.006 (3) | 0.002 (2) | 0.030 (3) |
C9B | 0.051 (2) | 0.074 (3) | 0.069 (3) | 0.009 (2) | 0.000 (2) | 0.024 (2) |
N1B | 0.056 (2) | 0.084 (3) | 0.059 (2) | −0.002 (2) | −0.0060 (19) | 0.010 (2) |
C17B | 0.071 (4) | 0.153 (6) | 0.065 (3) | −0.010 (4) | −0.011 (3) | 0.014 (4) |
C2B | 0.050 (3) | 0.078 (3) | 0.071 (3) | −0.002 (2) | 0.016 (2) | −0.004 (3) |
C1B | 0.065 (3) | 0.095 (3) | 0.055 (3) | −0.001 (3) | 0.016 (2) | 0.006 (3) |
C13B | 0.045 (2) | 0.048 (2) | 0.053 (2) | 0.0065 (17) | 0.0048 (19) | 0.0074 (18) |
C5B | 0.046 (2) | 0.057 (2) | 0.055 (2) | 0.0102 (18) | 0.004 (2) | 0.001 (2) |
C6B | 0.056 (3) | 0.068 (3) | 0.068 (3) | 0.002 (2) | 0.002 (2) | −0.008 (2) |
C7B | 0.064 (3) | 0.049 (2) | 0.113 (4) | 0.000 (2) | 0.015 (3) | −0.007 (3) |
C8B | 0.055 (3) | 0.050 (2) | 0.102 (4) | 0.0072 (19) | 0.013 (3) | 0.017 (3) |
C14B | 0.043 (2) | 0.053 (2) | 0.069 (3) | 0.0095 (17) | 0.009 (2) | 0.012 (2) |
C16B | 0.062 (3) | 0.061 (3) | 0.064 (3) | −0.003 (2) | 0.004 (2) | 0.000 (2) |
C15B | 0.055 (2) | 0.047 (2) | 0.056 (2) | 0.0060 (18) | 0.006 (2) | 0.0039 (19) |
C18B | 0.062 (7) | 0.156 (11) | 0.070 (6) | −0.013 (7) | −0.017 (5) | 0.005 (7) |
C20C | 0.097 (5) | 0.208 (9) | 0.123 (6) | 0.071 (6) | −0.015 (5) | −0.020 (6) |
C19C | 0.091 (5) | 0.138 (6) | 0.141 (6) | 0.041 (5) | 0.005 (4) | −0.004 (6) |
C20B | 0.077 (8) | 0.235 (17) | 0.086 (7) | 0.007 (10) | −0.005 (6) | 0.013 (8) |
C1S | 0.164 (9) | 0.178 (9) | 0.158 (9) | −0.038 (8) | −0.053 (8) | 0.033 (8) |
C2S | 0.237 (14) | 0.232 (13) | 0.099 (7) | 0.080 (12) | 0.026 (8) | 0.008 (8) |
C4S | 0.137 (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—C20B | 1.427 (15) | C9C—C14C | 1.532 (7) |
C19B—C20' | 1.46 (3) | C9C—H9C | 0.98 |
C19B—C18B | 1.496 (12) | N1C—C17C | 1.463 (6) |
C19B—C18' | 1.62 (3) | N1C—C16C | 1.464 (6) |
C19B—H19A | 0.97 | C17C—C18C | 1.478 (8) |
C19B—H19B | 0.97 | C17C—H17C | 0.97 |
C19B—H19' | 0.97 | C17C—H17D | 0.97 |
C19B—H19" | 0.97 | C18C—C19C | 1.494 (8) |
O1A—C3A | 1.373 (5) | C18C—C20C | 1.497 (10) |
O1A—H1OA | 0.82 | C18C—H18C | 0.98 |
O2A—C4A | 1.387 (5) | C5C—C6C | 1.536 (7) |
O2A—C5A | 1.461 (5) | C5C—C13C | 1.546 (6) |
O4A—C14A | 1.439 (5) | C5C—H5C | 0.98 |
O4A—H4OA | 0.82 | C6C—C7C | 1.483 (8) |
O3A—C6A | 1.217 (5) | C7C—C8C | 1.523 (8) |
O1C—C3C | 1.380 (6) | C7C—H7C1 | 0.97 |
O1C—H1OC | 0.82 | C7C—H7C2 | 0.97 |
O2C—C4C | 1.400 (5) | C8C—C14C | 1.531 (6) |
O2C—C5C | 1.465 (6) | C8C—H8C1 | 0.97 |
O3C—C6C | 1.215 (6) | C8C—H8C2 | 0.97 |
O4C—C14C | 1.443 (5) | C14C—C13C | 1.533 (6) |
O4C—H4OC | 0.82 | C13C—C15C | 1.538 (6) |
O1B—C3B | 1.359 (5) | C15C—C16C | 1.520 (7) |
O1B—H1OB | 0.82 | C15C—H15C | 0.97 |
O2B—C4B | 1.391 (5) | C15C—H15D | 0.97 |
O2B—C5B | 1.467 (4) | C16C—H16C | 0.97 |
O4B—C14B | 1.446 (5) | C16C—H16D | 0.97 |
O4B—H4OB | 0.82 | C1C—C2C | 1.363 (7) |
C13A—C12A | 1.503 (5) | C1C—H1C | 0.93 |
C13A—C15A | 1.536 (5) | C2C—H2C | 0.93 |
C13A—C14A | 1.539 (5) | O1S—C3S | 1.210 (10) |
C13A—C5A | 1.549 (5) | C3S—C4S | 1.406 (13) |
N1A—C16A | 1.457 (5) | C12B—C11B | 1.363 (6) |
N1A—C17A | 1.462 (6) | C12B—C13B | 1.508 (5) |
N1A—C9A | 1.477 (5) | C11B—C1B | 1.406 (7) |
O3B—C6B | 1.195 (6) | C11B—C10B | 1.515 (7) |
C3B—C4B | 1.376 (6) | C10B—C9B | 1.545 (7) |
C3B—C2B | 1.380 (7) | C10B—H10E | 0.97 |
C4B—C12B | 1.381 (6) | C10B—H10F | 0.97 |
O2S—C3S | 1.268 (11) | C9B—N1B | 1.484 (6) |
O2S—C2S | 1.424 (11) | C9B—C14B | 1.548 (7) |
C3A—C4A | 1.376 (6) | C9B—H9B | 0.98 |
C3A—C2A | 1.386 (7) | N1B—C16B | 1.473 (6) |
C4A—C12A | 1.369 (6) | N1B—C17B | 1.483 (7) |
C12A—C11A | 1.378 (6) | C17B—C18B | 1.460 (13) |
C15A—C16A | 1.514 (6) | C17B—C18' | 1.61 (3) |
C15A—H15A | 0.97 | C17B—H17E | 0.97 |
C15A—H15B | 0.97 | C17B—H17F | 0.97 |
C16A—H16A | 0.97 | C2B—C1B | 1.391 (7) |
C16A—H16B | 0.97 | C2B—H2B | 0.93 |
C17A—C18A | 1.489 (8) | C1B—H1B | 0.93 |
C17A—H17A | 0.97 | C13B—C15B | 1.526 (6) |
C17A—H17B | 0.97 | C13B—C14B | 1.528 (5) |
C18A—C20A | 1.436 (8) | C13B—C5B | 1.553 (6) |
C18A—C19A | 1.480 (8) | C5B—C6B | 1.527 (6) |
C18A—H18A | 0.98 | C5B—H5B | 0.98 |
C20A—C19A | 1.454 (8) | C6B—C7B | 1.503 (7) |
C20A—H20A | 0.97 | C7B—C8B | 1.532 (8) |
C20A—H20B | 0.97 | C7B—H7B1 | 0.97 |
C5A—C6A | 1.522 (6) | C7B—H7B2 | 0.97 |
C5A—H5A | 0.98 | C8B—C14B | 1.511 (6) |
C19A—H19C | 0.97 | C8B—H8B1 | 0.97 |
C19A—H19D | 0.97 | C8B—H8B2 | 0.97 |
C9A—C14A | 1.546 (6) | C16B—C15B | 1.508 (6) |
C9A—C10A | 1.549 (6) | C16B—H16E | 0.97 |
C9A—H9A | 0.98 | C16B—H16F | 0.97 |
C10A—C11A | 1.504 (6) | C15B—H15E | 0.97 |
C10A—H10A | 0.97 | C15B—H15F | 0.97 |
C10A—H10B | 0.97 | C18B—C20B | 1.45 (2) |
C11A—C1A | 1.392 (6) | C18B—H18B | 0.98 |
C1A—C2A | 1.376 (7) | C20C—C19C | 1.502 (11) |
C1A—H1A | 0.93 | C20C—H20C | 0.97 |
C2A—H2A | 0.93 | C20C—H20D | 0.97 |
C14A—C8A | 1.508 (5) | C19C—H19E | 0.97 |
C8A—C7A | 1.529 (6) | C19C—H19F | 0.97 |
C8A—H8A1 | 0.97 | C20B—H20E | 0.97 |
C8A—H8A2 | 0.97 | C20B—H20F | 0.97 |
C7A—C6A | 1.484 (7) | C1S—C2S | 1.419 (14) |
C7A—H7A1 | 0.97 | C1S—H1S1 | 0.96 |
C7A—H7A2 | 0.97 | C1S—H1S2 | 0.96 |
C3C—C4C | 1.357 (6) | C1S—H1S3 | 0.96 |
C3C—C2C | 1.396 (7) | C2S—H2S1 | 0.97 |
C4C—C12C | 1.362 (6) | C2S—H2S2 | 0.97 |
C12C—C11C | 1.373 (6) | C4S—H4S1 | 0.96 |
C12C—C13C | 1.494 (6) | C4S—H4S2 | 0.96 |
C11C—C1C | 1.400 (7) | C4S—H4S3 | 0.96 |
C11C—C10C | 1.494 (7) | C18'—C20' | 1.53 (5) |
C10C—C9C | 1.534 (7) | C18'—H18' | 0.98 |
C10C—H10C | 0.97 | C20'—H20G | 0.97 |
C10C—H10D | 0.97 | C20'—H20H | 0.97 |
C9C—N1C | 1.482 (6) | | |
| | | |
C20B—C19B—C18B | 59.5 (9) | C6C—C7C—C8C | 111.7 (4) |
C20'—C19B—C18' | 59.4 (17) | C6C—C7C—H7C1 | 109.3 |
C20B—C19B—H19A | 117.8 | C8C—C7C—H7C1 | 109.3 |
C18B—C19B—H19A | 117.8 | C6C—C7C—H7C2 | 109.3 |
C20B—C19B—H19B | 117.8 | C8C—C7C—H7C2 | 109.3 |
C18B—C19B—H19B | 117.8 | H7C1—C7C—H7C2 | 107.9 |
H19A—C19B—H19B | 115 | C7C—C8C—C14C | 111.0 (4) |
C20'—C19B—H19' | 116.5 | C7C—C8C—H8C1 | 109.4 |
C18'—C19B—H19' | 118.2 | C14C—C8C—H8C1 | 109.4 |
C20'—C19B—H19" | 118.1 | C7C—C8C—H8C2 | 109.4 |
C18'—C19B—H19" | 117.8 | C14C—C8C—H8C2 | 109.4 |
H19'—C19B—H19" | 115.4 | H8C1—C8C—H8C2 | 108 |
C3A—O1A—H1OA | 109.5 | O4C—C14C—C8C | 105.9 (4) |
C4A—O2A—C5A | 103.8 (3) | O4C—C14C—C9C | 107.8 (4) |
C14A—O4A—H4OA | 109.5 | C8C—C14C—C9C | 113.7 (4) |
C3C—O1C—H1OC | 109.5 | O4C—C14C—C13C | 112.3 (4) |
C4C—O2C—C5C | 104.3 (3) | C8C—C14C—C13C | 110.9 (4) |
C14C—O4C—H4OC | 109.5 | C9C—C14C—C13C | 106.4 (4) |
C3B—O1B—H1OB | 109.5 | C12C—C13C—C14C | 108.1 (3) |
C4B—O2B—C5B | 104.0 (3) | C12C—C13C—C15C | 110.5 (4) |
C14B—O4B—H4OB | 109.5 | C14C—C13C—C15C | 109.2 (4) |
C12A—C13A—C15A | 110.9 (3) | C12C—C13C—C5C | 98.2 (3) |
C12A—C13A—C14A | 108.0 (3) | C14C—C13C—C5C | 117.8 (4) |
C15A—C13A—C14A | 109.2 (3) | C15C—C13C—C5C | 112.4 (4) |
C12A—C13A—C5A | 98.2 (3) | C16C—C15C—C13C | 110.6 (4) |
C15A—C13A—C5A | 112.7 (3) | C16C—C15C—H15C | 109.5 |
C14A—C13A—C5A | 117.3 (3) | C13C—C15C—H15C | 109.5 |
C16A—N1A—C17A | 113.1 (4) | C16C—C15C—H15D | 109.5 |
C16A—N1A—C9A | 112.1 (3) | C13C—C15C—H15D | 109.5 |
C17A—N1A—C9A | 112.9 (3) | H15C—C15C—H15D | 108.1 |
O1B—C3B—C4B | 125.1 (4) | N1C—C16C—C15C | 112.1 (4) |
O1B—C3B—C2B | 119.4 (4) | N1C—C16C—H16C | 109.2 |
C4B—C3B—C2B | 115.5 (4) | C15C—C16C—H16C | 109.2 |
C3B—C4B—C12B | 121.5 (4) | N1C—C16C—H16D | 109.2 |
C3B—C4B—O2B | 126.8 (4) | C15C—C16C—H16D | 109.2 |
C12B—C4B—O2B | 111.7 (3) | H16C—C16C—H16D | 107.9 |
C3S—O2S—C2S | 119.8 (9) | C2C—C1C—C11C | 121.3 (4) |
O1A—C3A—C4A | 123.2 (4) | C2C—C1C—H1C | 119.4 |
O1A—C3A—C2A | 119.9 (4) | C11C—C1C—H1C | 119.4 |
C4A—C3A—C2A | 116.8 (4) | C1C—C2C—C3C | 121.9 (5) |
C12A—C4A—C3A | 120.4 (4) | C1C—C2C—H2C | 119.1 |
C12A—C4A—O2A | 112.5 (3) | C3C—C2C—H2C | 119.1 |
C3A—C4A—O2A | 127.0 (4) | O1S—C3S—O2S | 121.4 (11) |
C4A—C12A—C11A | 124.0 (4) | O1S—C3S—C4S | 118.8 (11) |
C4A—C12A—C13A | 108.7 (3) | O2S—C3S—C4S | 118.4 (9) |
C11A—C12A—C13A | 127.2 (4) | C11B—C12B—C4B | 123.9 (4) |
C16A—C15A—C13A | 110.8 (3) | C11B—C12B—C13B | 126.9 (4) |
C16A—C15A—H15A | 109.5 | C4B—C12B—C13B | 109.2 (3) |
C13A—C15A—H15A | 109.5 | C12B—C11B—C1B | 115.4 (4) |
C16A—C15A—H15B | 109.5 | C12B—C11B—C10B | 118.8 (4) |
C13A—C15A—H15B | 109.5 | C1B—C11B—C10B | 125.7 (4) |
H15A—C15A—H15B | 108.1 | C11B—C10B—C9B | 113.1 (4) |
N1A—C16A—C15A | 111.6 (4) | C11B—C10B—H10E | 109 |
N1A—C16A—H16A | 109.3 | C9B—C10B—H10E | 109 |
C15A—C16A—H16A | 109.3 | C11B—C10B—H10F | 109 |
N1A—C16A—H16B | 109.3 | C9B—C10B—H10F | 109 |
C15A—C16A—H16B | 109.3 | H10E—C10B—H10F | 107.8 |
H16A—C16A—H16B | 108 | N1B—C9B—C10B | 116.1 (4) |
N1A—C17A—C18A | 112.6 (5) | N1B—C9B—C14B | 104.9 (3) |
N1A—C17A—H17A | 109.1 | C10B—C9B—C14B | 115.1 (4) |
C18A—C17A—H17A | 109.1 | N1B—C9B—H9B | 106.7 |
N1A—C17A—H17B | 109.1 | C10B—C9B—H9B | 106.7 |
C18A—C17A—H17B | 109.1 | C14B—C9B—H9B | 106.7 |
H17A—C17A—H17B | 107.8 | C16B—N1B—C17B | 111.0 (5) |
C20A—C18A—C19A | 59.8 (4) | C16B—N1B—C9B | 112.4 (3) |
C20A—C18A—C17A | 119.8 (6) | C17B—N1B—C9B | 112.5 (4) |
C19A—C18A—C17A | 118.2 (6) | C18B—C17B—N1B | 115.3 (6) |
C20A—C18A—H18A | 115.8 | N1B—C17B—C18' | 108.3 (11) |
C19A—C18A—H18A | 115.8 | C18B—C17B—H17E | 108.4 |
C17A—C18A—H18A | 115.8 | N1B—C17B—H17E | 108.4 |
C18A—C20A—C19A | 61.6 (4) | C18B—C17B—H17F | 108.4 |
C18A—C20A—H20A | 117.6 | N1B—C17B—H17F | 108.4 |
C19A—C20A—H20A | 117.6 | H17E—C17B—H17F | 107.5 |
C18A—C20A—H20B | 117.6 | C3B—C2B—C1B | 123.4 (4) |
C19A—C20A—H20B | 117.6 | C3B—C2B—H2B | 118.3 |
H20A—C20A—H20B | 114.7 | C1B—C2B—H2B | 118.3 |
O2A—C5A—C6A | 108.8 (3) | C2B—C1B—C11B | 120.3 (4) |
O2A—C5A—C13A | 104.9 (3) | C2B—C1B—H1B | 119.9 |
C6A—C5A—C13A | 113.6 (3) | C11B—C1B—H1B | 119.9 |
O2A—C5A—H5A | 109.8 | C12B—C13B—C15B | 110.2 (3) |
C6A—C5A—H5A | 109.8 | C12B—C13B—C14B | 108.6 (3) |
C13A—C5A—H5A | 109.8 | C15B—C13B—C14B | 109.1 (3) |
C20A—C19A—C18A | 58.6 (4) | C12B—C13B—C5B | 97.3 (3) |
C20A—C19A—H19C | 117.9 | C15B—C13B—C5B | 113.2 (3) |
C18A—C19A—H19C | 117.9 | C14B—C13B—C5B | 117.6 (3) |
C20A—C19A—H19D | 117.9 | O2B—C5B—C6B | 108.6 (3) |
C18A—C19A—H19D | 117.9 | O2B—C5B—C13B | 105.2 (3) |
H19C—C19A—H19D | 115.1 | C6B—C5B—C13B | 113.2 (4) |
N1A—C9A—C14A | 105.1 (3) | O2B—C5B—H5B | 109.9 |
N1A—C9A—C10A | 116.6 (4) | C6B—C5B—H5B | 109.9 |
C14A—C9A—C10A | 114.5 (3) | C13B—C5B—H5B | 109.9 |
N1A—C9A—H9A | 106.7 | O3B—C6B—C7B | 122.9 (5) |
C14A—C9A—H9A | 106.7 | O3B—C6B—C5B | 121.5 (4) |
C10A—C9A—H9A | 106.7 | C7B—C6B—C5B | 115.5 (4) |
C11A—C10A—C9A | 114.6 (3) | C6B—C7B—C8B | 109.3 (4) |
C11A—C10A—H10A | 108.6 | C6B—C7B—H7B1 | 109.8 |
C9A—C10A—H10A | 108.6 | C8B—C7B—H7B1 | 109.8 |
C11A—C10A—H10B | 108.6 | C6B—C7B—H7B2 | 109.8 |
C9A—C10A—H10B | 108.6 | C8B—C7B—H7B2 | 109.8 |
H10A—C10A—H10B | 107.6 | H7B1—C7B—H7B2 | 108.3 |
C12A—C11A—C1A | 115.2 (4) | C14B—C8B—C7B | 110.6 (4) |
C12A—C11A—C10A | 117.9 (4) | C14B—C8B—H8B1 | 109.5 |
C1A—C11A—C10A | 126.7 (4) | C7B—C8B—H8B1 | 109.5 |
C2A—C1A—C11A | 121.4 (5) | C14B—C8B—H8B2 | 109.5 |
C2A—C1A—H1A | 119.3 | C7B—C8B—H8B2 | 109.5 |
C11A—C1A—H1A | 119.3 | H8B1—C8B—H8B2 | 108.1 |
C1A—C2A—C3A | 122.1 (4) | O4B—C14B—C8B | 106.1 (4) |
C1A—C2A—H2A | 119 | O4B—C14B—C13B | 110.9 (3) |
C3A—C2A—H2A | 119 | C8B—C14B—C13B | 112.5 (4) |
O4A—C14A—C8A | 106.8 (3) | O4B—C14B—C9B | 107.2 (3) |
O4A—C14A—C13A | 111.1 (3) | C8B—C14B—C9B | 114.1 (4) |
C8A—C14A—C13A | 111.8 (3) | C13B—C14B—C9B | 106.0 (4) |
O4A—C14A—C9A | 107.5 (3) | N1B—C16B—C15B | 110.9 (4) |
C8A—C14A—C9A | 113.9 (3) | N1B—C16B—H16E | 109.5 |
C13A—C14A—C9A | 105.7 (3) | C15B—C16B—H16E | 109.5 |
C14A—C8A—C7A | 110.2 (3) | N1B—C16B—H16F | 109.5 |
C14A—C8A—H8A1 | 109.6 | C15B—C16B—H16F | 109.5 |
C7A—C8A—H8A1 | 109.6 | H16E—C16B—H16F | 108 |
C14A—C8A—H8A2 | 109.6 | C16B—C15B—C13B | 111.0 (4) |
C7A—C8A—H8A2 | 109.6 | C16B—C15B—H15E | 109.4 |
H8A1—C8A—H8A2 | 108.1 | C13B—C15B—H15E | 109.4 |
C6A—C7A—C8A | 111.2 (4) | C16B—C15B—H15F | 109.4 |
C6A—C7A—H7A1 | 109.4 | C13B—C15B—H15F | 109.4 |
C8A—C7A—H7A1 | 109.4 | H15E—C15B—H15F | 108 |
C6A—C7A—H7A2 | 109.4 | C20B—C18B—C17B | 115.5 (14) |
C8A—C7A—H7A2 | 109.4 | C20B—C18B—C19B | 57.9 (7) |
H7A1—C7A—H7A2 | 108 | C17B—C18B—C19B | 118.2 (9) |
O3A—C6A—C7A | 122.0 (5) | C20B—C18B—H18B | 117.3 |
O3A—C6A—C5A | 120.0 (4) | C17B—C18B—H18B | 117.3 |
C7A—C6A—C5A | 118.0 (4) | C19B—C18B—H18B | 117.3 |
C4C—C3C—O1C | 125.1 (4) | C18C—C20C—C19C | 59.8 (5) |
C4C—C3C—C2C | 116.4 (5) | C18C—C20C—H20C | 117.8 |
O1C—C3C—C2C | 118.5 (5) | C19C—C20C—H20C | 117.8 |
C3C—C4C—C12C | 121.9 (4) | C18C—C20C—H20D | 117.8 |
C3C—C4C—O2C | 126.6 (4) | C19C—C20C—H20D | 117.8 |
C12C—C4C—O2C | 111.5 (4) | H20C—C20C—H20D | 114.9 |
C4C—C12C—C11C | 123.1 (4) | C18C—C19C—C20C | 60.0 (5) |
C4C—C12C—C13C | 110.0 (4) | C18C—C19C—H19E | 117.8 |
C11C—C12C—C13C | 127.0 (4) | C20C—C19C—H19E | 117.8 |
C12C—C11C—C1C | 115.4 (4) | C18C—C19C—H19F | 117.8 |
C12C—C11C—C10C | 118.1 (4) | C20C—C19C—H19F | 117.8 |
C1C—C11C—C10C | 126.1 (4) | H19E—C19C—H19F | 114.9 |
C11C—C10C—C9C | 114.1 (4) | C19B—C20B—C18B | 62.6 (8) |
C11C—C10C—H10C | 108.7 | C19B—C20B—H20E | 117.5 |
C9C—C10C—H10C | 108.7 | C18B—C20B—H20E | 117.5 |
C11C—C10C—H10D | 108.7 | C19B—C20B—H20F | 117.5 |
C9C—C10C—H10D | 108.7 | C18B—C20B—H20F | 117.5 |
H10C—C10C—H10D | 107.6 | H20E—C20B—H20F | 114.6 |
N1C—C9C—C14C | 104.7 (4) | C2S—C1S—H1S1 | 109.5 |
N1C—C9C—C10C | 117.1 (5) | C2S—C1S—H1S2 | 109.5 |
C14C—C9C—C10C | 114.7 (4) | H1S1—C1S—H1S2 | 109.5 |
N1C—C9C—H9C | 106.5 | C2S—C1S—H1S3 | 109.5 |
C14C—C9C—H9C | 106.5 | H1S1—C1S—H1S3 | 109.5 |
C10C—C9C—H9C | 106.5 | H1S2—C1S—H1S3 | 109.5 |
C17C—N1C—C16C | 113.4 (4) | C1S—C2S—O2S | 110.4 (9) |
C17C—N1C—C9C | 113.2 (4) | C1S—C2S—H2S1 | 109.6 |
C16C—N1C—C9C | 112.4 (4) | O2S—C2S—H2S1 | 109.6 |
N1C—C17C—C18C | 112.9 (5) | C1S—C2S—H2S2 | 109.6 |
N1C—C17C—H17C | 109 | O2S—C2S—H2S2 | 109.6 |
C18C—C17C—H17C | 109 | H2S1—C2S—H2S2 | 108.1 |
N1C—C17C—H17D | 109 | C3S—C4S—H4S1 | 109.5 |
C18C—C17C—H17D | 109 | C3S—C4S—H4S2 | 109.5 |
H17C—C17C—H17D | 107.8 | H4S1—C4S—H4S2 | 109.5 |
C17C—C18C—C19C | 117.5 (6) | C3S—C4S—H4S3 | 109.5 |
C17C—C18C—C20C | 119.6 (7) | H4S1—C4S—H4S3 | 109.5 |
C19C—C18C—C20C | 60.3 (5) | H4S2—C4S—H4S3 | 109.5 |
C17C—C18C—H18C | 116 | C20'—C18'—C17B | 113 (2) |
C19C—C18C—H18C | 116 | C20'—C18'—C19B | 55.2 (14) |
C20C—C18C—H18C | 116 | C17B—C18'—C19B | 103.3 (15) |
O2C—C5C—C6C | 108.3 (4) | C20'—C18'—H18' | 122.1 |
O2C—C5C—C13C | 105.0 (3) | C17B—C18'—H18' | 122.1 |
C6C—C5C—C13C | 114.3 (4) | C19B—C18'—H18' | 122.1 |
O2C—C5C—H5C | 109.7 | C19B—C20'—C18' | 65.5 (16) |
C6C—C5C—H5C | 109.7 | C19B—C20'—H20G | 117.2 |
C13C—C5C—H5C | 109.7 | C18'—C20'—H20G | 117.2 |
O3C—C6C—C7C | 123.7 (5) | C19B—C20'—H20H | 117.2 |
O3C—C6C—C5C | 118.7 (6) | C18'—C20'—H20H | 117.2 |
C7C—C6C—C5C | 117.6 (4) | H20G—C20'—H20H | 114.2 |
| | | |
O1B—C3B—C4B—C12B | −179.4 (4) | C4C—C12C—C13C—C15C | −94.8 (4) |
C2B—C3B—C4B—C12B | 1.3 (7) | C11C—C12C—C13C—C15C | 84.6 (5) |
O1B—C3B—C4B—O2B | 2.7 (7) | C4C—C12C—C13C—C5C | 22.8 (5) |
C2B—C3B—C4B—O2B | −176.6 (4) | C11C—C12C—C13C—C5C | −157.7 (4) |
C5B—O2B—C4B—C3B | 160.7 (4) | O4C—C14C—C13C—C12C | 173.7 (4) |
C5B—O2B—C4B—C12B | −17.4 (4) | C8C—C14C—C13C—C12C | −68.0 (5) |
O1A—C3A—C4A—C12A | −178.6 (4) | C9C—C14C—C13C—C12C | 56.0 (4) |
C2A—C3A—C4A—C12A | 2.5 (7) | O4C—C14C—C13C—C15C | 53.5 (5) |
O1A—C3A—C4A—O2A | 4.8 (8) | C8C—C14C—C13C—C15C | 171.7 (4) |
C2A—C3A—C4A—O2A | −174.1 (4) | C9C—C14C—C13C—C15C | −64.3 (5) |
C5A—O2A—C4A—C12A | −18.9 (4) | O4C—C14C—C13C—C5C | −76.2 (5) |
C5A—O2A—C4A—C3A | 158.0 (5) | C8C—C14C—C13C—C5C | 42.0 (5) |
C3A—C4A—C12A—C11A | −3.8 (7) | C9C—C14C—C13C—C5C | 166.0 (4) |
O2A—C4A—C12A—C11A | 173.3 (4) | O2C—C5C—C13C—C12C | −31.8 (4) |
C3A—C4A—C12A—C13A | 179.7 (4) | C6C—C5C—C13C—C12C | 86.7 (4) |
O2A—C4A—C12A—C13A | −3.2 (5) | O2C—C5C—C13C—C14C | −147.3 (4) |
C15A—C13A—C12A—C4A | −96.1 (4) | C6C—C5C—C13C—C14C | −28.8 (5) |
C14A—C13A—C12A—C4A | 144.3 (4) | O2C—C5C—C13C—C15C | 84.4 (4) |
C5A—C13A—C12A—C4A | 22.1 (4) | C6C—C5C—C13C—C15C | −157.0 (4) |
C15A—C13A—C12A—C11A | 87.6 (5) | C12C—C13C—C15C—C16C | −65.2 (5) |
C14A—C13A—C12A—C11A | −32.0 (5) | C14C—C13C—C15C—C16C | 53.5 (5) |
C5A—C13A—C12A—C11A | −154.2 (4) | C5C—C13C—C15C—C16C | −173.8 (4) |
C12A—C13A—C15A—C16A | −64.7 (4) | C17C—N1C—C16C—C15C | −173.0 (4) |
C14A—C13A—C15A—C16A | 54.3 (4) | C9C—N1C—C16C—C15C | 57.1 (6) |
C5A—C13A—C15A—C16A | −173.6 (3) | C13C—C15C—C16C—N1C | −49.0 (6) |
C17A—N1A—C16A—C15A | −172.6 (4) | C12C—C11C—C1C—C2C | −0.2 (7) |
C9A—N1A—C16A—C15A | 58.4 (5) | C10C—C11C—C1C—C2C | 172.3 (5) |
C13A—C15A—C16A—N1A | −50.4 (5) | C11C—C1C—C2C—C3C | −2.6 (8) |
C16A—N1A—C17A—C18A | 85.4 (6) | C4C—C3C—C2C—C1C | 3.1 (8) |
C9A—N1A—C17A—C18A | −146.0 (5) | O1C—C3C—C2C—C1C | −174.5 (5) |
N1A—C17A—C18A—C20A | 84.1 (7) | C2S—O2S—C3S—O1S | −9.8 (17) |
N1A—C17A—C18A—C19A | 153.6 (5) | C2S—O2S—C3S—C4S | −176.3 (12) |
C17A—C18A—C20A—C19A | 107.3 (7) | C3B—C4B—C12B—C11B | −3.3 (7) |
C4A—O2A—C5A—C6A | −89.4 (4) | O2B—C4B—C12B—C11B | 174.9 (4) |
C4A—O2A—C5A—C13A | 32.5 (4) | C3B—C4B—C12B—C13B | 176.1 (4) |
C12A—C13A—C5A—O2A | −32.8 (4) | O2B—C4B—C12B—C13B | −5.6 (5) |
C15A—C13A—C5A—O2A | 84.1 (4) | C4B—C12B—C11B—C1B | 3.1 (7) |
C14A—C13A—C5A—O2A | −148.0 (3) | C13B—C12B—C11B—C1B | −176.2 (4) |
C12A—C13A—C5A—C6A | 86.0 (4) | C4B—C12B—C11B—C10B | −172.5 (4) |
C15A—C13A—C5A—C6A | −157.2 (3) | C13B—C12B—C11B—C10B | 8.2 (7) |
C14A—C13A—C5A—C6A | −29.2 (5) | C12B—C11B—C10B—C9B | −8.3 (7) |
C17A—C18A—C19A—C20A | −109.9 (7) | C1B—C11B—C10B—C9B | 176.6 (5) |
C16A—N1A—C9A—C14A | −66.9 (4) | C11B—C10B—C9B—N1B | −86.6 (5) |
C17A—N1A—C9A—C14A | 164.0 (4) | C11B—C10B—C9B—C14B | 36.5 (6) |
C16A—N1A—C9A—C10A | 61.2 (5) | C10B—C9B—N1B—C16B | 62.6 (5) |
C17A—N1A—C9A—C10A | −68.0 (5) | C14B—C9B—N1B—C16B | −65.7 (4) |
N1A—C9A—C10A—C11A | −90.8 (5) | C10B—C9B—N1B—C17B | −63.6 (6) |
C14A—C9A—C10A—C11A | 32.5 (5) | C14B—C9B—N1B—C17B | 168.1 (4) |
C4A—C12A—C11A—C1A | 2.2 (7) | C16B—N1B—C17B—C18B | 72.4 (9) |
C13A—C12A—C11A—C1A | 178.0 (4) | C9B—N1B—C17B—C18B | −160.6 (8) |
C4A—C12A—C11A—C10A | −173.8 (4) | C16B—N1B—C17B—C18' | 106.1 (13) |
C13A—C12A—C11A—C10A | 2.0 (6) | C9B—N1B—C17B—C18' | −126.9 (12) |
C9A—C10A—C11A—C12A | −1.4 (6) | O1B—C3B—C2B—C1B | −178.8 (5) |
C9A—C10A—C11A—C1A | −176.9 (5) | C4B—C3B—C2B—C1B | 0.5 (7) |
C12A—C11A—C1A—C2A | 0.5 (7) | C3B—C2B—C1B—C11B | −0.6 (8) |
C10A—C11A—C1A—C2A | 176.1 (5) | C12B—C11B—C1B—C2B | −1.2 (7) |
C11A—C1A—C2A—C3A | −1.6 (8) | C10B—C11B—C1B—C2B | 174.0 (5) |
O1A—C3A—C2A—C1A | −178.8 (5) | C11B—C12B—C13B—C15B | 85.6 (5) |
C4A—C3A—C2A—C1A | 0.1 (7) | C4B—C12B—C13B—C15B | −93.8 (4) |
C12A—C13A—C14A—O4A | 173.7 (3) | C11B—C12B—C13B—C14B | −33.9 (6) |
C15A—C13A—C14A—O4A | 53.0 (4) | C4B—C12B—C13B—C14B | 146.7 (4) |
C5A—C13A—C14A—O4A | −76.7 (4) | C11B—C12B—C13B—C5B | −156.3 (4) |
C12A—C13A—C14A—C8A | −67.0 (4) | C4B—C12B—C13B—C5B | 24.3 (4) |
C15A—C13A—C14A—C8A | 172.2 (3) | C4B—O2B—C5B—C6B | −88.6 (4) |
C5A—C13A—C14A—C8A | 42.6 (5) | C4B—O2B—C5B—C13B | 32.8 (4) |
C12A—C13A—C14A—C9A | 57.4 (4) | C12B—C13B—C5B—O2B | −34.1 (4) |
C15A—C13A—C14A—C9A | −63.3 (4) | C15B—C13B—C5B—O2B | 81.6 (4) |
C5A—C13A—C14A—C9A | 167.1 (3) | C14B—C13B—C5B—O2B | −149.6 (3) |
N1A—C9A—C14A—O4A | −50.7 (4) | C12B—C13B—C5B—C6B | 84.3 (4) |
C10A—C9A—C14A—O4A | −180.0 (3) | C15B—C13B—C5B—C6B | −160.0 (4) |
N1A—C9A—C14A—C8A | −168.8 (3) | C14B—C13B—C5B—C6B | −31.2 (5) |
C10A—C9A—C14A—C8A | 61.9 (5) | O2B—C5B—C6B—O3B | −19.5 (7) |
N1A—C9A—C14A—C13A | 68.0 (4) | C13B—C5B—C6B—O3B | −135.9 (5) |
C10A—C9A—C14A—C13A | −61.3 (4) | O2B—C5B—C6B—C7B | 156.1 (4) |
O4A—C14A—C8A—C7A | 64.5 (4) | C13B—C5B—C6B—C7B | 39.8 (6) |
C13A—C14A—C8A—C7A | −57.2 (5) | O3B—C6B—C7B—C8B | 119.6 (6) |
C9A—C14A—C8A—C7A | −177.0 (4) | C5B—C6B—C7B—C8B | −55.9 (6) |
C14A—C8A—C7A—C6A | 60.6 (5) | C6B—C7B—C8B—C14B | 63.1 (5) |
C8A—C7A—C6A—O3A | 129.6 (5) | C7B—C8B—C14B—O4B | 66.4 (5) |
C8A—C7A—C6A—C5A | −49.0 (5) | C7B—C8B—C14B—C13B | −55.0 (5) |
O2A—C5A—C6A—O3A | −29.3 (5) | C7B—C8B—C14B—C9B | −175.8 (4) |
C13A—C5A—C6A—O3A | −145.7 (4) | C12B—C13B—C14B—O4B | 171.9 (3) |
O2A—C5A—C6A—C7A | 149.5 (4) | C15B—C13B—C14B—O4B | 51.8 (5) |
C13A—C5A—C6A—C7A | 33.0 (5) | C5B—C13B—C14B—O4B | −78.9 (4) |
O1C—C3C—C4C—C12C | 176.6 (5) | C12B—C13B—C14B—C8B | −69.5 (5) |
C2C—C3C—C4C—C12C | −0.9 (7) | C15B—C13B—C14B—C8B | 170.4 (4) |
O1C—C3C—C4C—O2C | −0.2 (8) | C5B—C13B—C14B—C8B | 39.7 (5) |
C2C—C3C—C4C—O2C | −177.6 (4) | C12B—C13B—C14B—C9B | 55.9 (4) |
C5C—O2C—C4C—C3C | 160.7 (5) | C15B—C13B—C14B—C9B | −64.3 (4) |
C5C—O2C—C4C—C12C | −16.4 (5) | C5B—C13B—C14B—C9B | 165.0 (4) |
C3C—C4C—C12C—C11C | −2.0 (7) | N1B—C9B—C14B—O4B | −51.0 (4) |
O2C—C4C—C12C—C11C | 175.3 (4) | C10B—C9B—C14B—O4B | −179.9 (4) |
C3C—C4C—C12C—C13C | 177.5 (4) | N1B—C9B—C14B—C8B | −168.2 (3) |
O2C—C4C—C12C—C13C | −5.2 (5) | C10B—C9B—C14B—C8B | 62.9 (5) |
C4C—C12C—C11C—C1C | 2.4 (7) | N1B—C9B—C14B—C13B | 67.5 (4) |
C13C—C12C—C11C—C1C | −177.0 (4) | C10B—C9B—C14B—C13B | −61.4 (5) |
C4C—C12C—C11C—C10C | −170.7 (5) | C17B—N1B—C16B—C15B | −175.1 (4) |
C13C—C12C—C11C—C10C | 9.9 (7) | C9B—N1B—C16B—C15B | 57.9 (5) |
C12C—C11C—C10C—C9C | −9.3 (7) | N1B—C16B—C15B—C13B | −51.1 (5) |
C1C—C11C—C10C—C9C | 178.3 (5) | C12B—C13B—C15B—C16B | −63.2 (4) |
C11C—C10C—C9C—N1C | −86.7 (6) | C14B—C13B—C15B—C16B | 56.0 (5) |
C11C—C10C—C9C—C14C | 36.7 (6) | C5B—C13B—C15B—C16B | −170.9 (4) |
C14C—C9C—N1C—C17C | 163.7 (4) | N1B—C17B—C18B—C20B | 96.2 (9) |
C10C—C9C—N1C—C17C | −67.9 (5) | C18'—C17B—C18B—C20B | 12 (2) |
C14C—C9C—N1C—C16C | −66.2 (5) | N1B—C17B—C18B—C19B | 161.9 (10) |
C10C—C9C—N1C—C16C | 62.1 (5) | C18'—C17B—C18B—C19B | 78 (2) |
C16C—N1C—C17C—C18C | 67.2 (6) | C20'—C19B—C18B—C20B | −77.1 (18) |
C9C—N1C—C17C—C18C | −163.3 (5) | C18'—C19B—C18B—C20B | 25 (2) |
N1C—C17C—C18C—C19C | −168.1 (6) | C20B—C19B—C18B—C17B | −103.8 (16) |
N1C—C17C—C18C—C20C | −98.4 (7) | C20'—C19B—C18B—C17B | 179 (3) |
C4C—O2C—C5C—C6C | −92.0 (4) | C18'—C19B—C18B—C17B | −79 (3) |
C4C—O2C—C5C—C13C | 30.5 (4) | C17C—C18C—C20C—C19C | −106.7 (7) |
O2C—C5C—C6C—O3C | −32.3 (6) | C17C—C18C—C19C—C20C | 110.1 (8) |
C13C—C5C—C6C—O3C | −149.0 (5) | C20'—C19B—C20B—C18B | 53.8 (12) |
O2C—C5C—C6C—C7C | 148.0 (4) | C18'—C19B—C20B—C18B | −24 (2) |
C13C—C5C—C6C—C7C | 31.3 (6) | C17B—C18B—C20B—C19B | 108.6 (10) |
O3C—C6C—C7C—C8C | 133.0 (5) | C3S—O2S—C2S—C1S | 168.5 (10) |
C5C—C6C—C7C—C8C | −47.3 (6) | C18B—C17B—C18'—C20' | 2.8 (12) |
C6C—C7C—C8C—C14C | 60.2 (5) | N1B—C17B—C18'—C20' | −106.0 (18) |
C7C—C8C—C14C—O4C | 65.2 (5) | C18B—C17B—C18'—C19B | −54.7 (18) |
C7C—C8C—C14C—C9C | −176.6 (4) | N1B—C17B—C18'—C19B | −163.5 (11) |
C7C—C8C—C14C—C13C | −56.9 (5) | C20B—C19B—C18'—C20' | 82 (2) |
N1C—C9C—C14C—O4C | −51.9 (5) | C18B—C19B—C18'—C20' | −55 (2) |
C10C—C9C—C14C—O4C | 178.3 (4) | C20B—C19B—C18'—C17B | −169 (3) |
N1C—C9C—C14C—C8C | −169.0 (4) | C20'—C19B—C18'—C17B | 109 (2) |
C10C—C9C—C14C—C8C | 61.2 (6) | C18B—C19B—C18'—C17B | 53.5 (17) |
N1C—C9C—C14C—C13C | 68.7 (4) | C20B—C19B—C20'—C18' | −37.9 (11) |
C10C—C9C—C14C—C13C | −61.1 (5) | C18B—C19B—C20'—C18' | 36.6 (13) |
C4C—C12C—C13C—C14C | 145.8 (4) | C17B—C18'—C20'—C19B | −90.8 (18) |
C11C—C12C—C13C—C14C | −34.8 (6) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1OA···O4Ai | 0.82 | 1.90 | 2.710 (5) | 168 |
O4A—H4OA···O2Aii | 0.82 | 2.43 | 2.904 (4) | 118 |
O1B—H1OB···O4Biii | 0.82 | 1.92 | 2.728 (5) | 170 |
O4B—H4OB···O2Biv | 0.82 | 2.39 | 2.942 (4) | 126 |
O1C—H1OC···O4Cv | 0.82 | 1.88 | 2.672 (6) | 164 |
O4C—H4OC···O2Cvi | 0.82 | 2.84 | 3.125 (4) | 103 |
C8B—H8B2···O1S | 0.97 | 2.54 | 3.395 (10) | 147 |
C20B—H20E···O1Bvii | 0.97 | 2.66 | 3.589 (15) | 160 |
C18C—H18C···O3Cvi | 0.98 | 2.63 | 3.501 (7) | 148 |
C19A—H19D···Cg(A)Cviii | 0.97 | 2.84 | 3.772 (7) | 163 |
Symmetry codes: (i) x+1/2, −y+3/2, −z+2; (ii) x−1/2, −y+3/2, −z+2; (iii) x+1/2, −y+1/2, −z+2; (iv) x−1/2, −y+1/2, −z+2; (v) −x+1, y+1/2, −z+3/2; (vi) −x+1, y−1/2, −z+3/2; (vii) x−1, y, z; (viii) −x, y+1/2, −z+3/2. |
(4
R,4a
S,7a
R,12b
S)-3-Cyclopropylmethyl-4a,9-dihydroxy-2,4,5,6,7a,13-hexahydro-1
H-4,12-methanobenzofuro[3,2-
e]isoquinolin-7-one diethyl ether hemisolvate (naltrexone_Et2O)
top
Crystal data top
2C20H23NO4·C4H10O | Dx = 1.142 Mg m−3 |
Mr = 756.91 | Cu Kα radiation, λ = 1.54178 Å |
Orthorhombic, P212121 | Cell parameters from 2455 reflections |
a = 12.5992 (2) Å | θ = 3.8–50.1° |
b = 13.1093 (3) Å | µ = 0.64 mm−1 |
c = 26.6586 (6) Å | T = 296 K |
V = 4403.11 (16) Å3 | Needle, colourless |
Z = 4 | 0.20 × 0.10 × 0.08 mm |
F(000) = 1624 | |
Data collection top
Bruker APEXII CCD diffractometer | 5222 reflections with I > 2σ(I) |
CCD scans | Rint = 0.059 |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | θmax = 66.5°, θmin = 3.3° |
Tmin = 0.843, Tmax = 0.950 | h = −14→14 |
22971 measured reflections | k = −13→15 |
7390 independent reflections | l = −31→31 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-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 = 1.10 | Δρmax = 0.53 e Å−3 |
7390 reflections | Δρmin = −0.26 e Å−3 |
545 parameters | Absolute structure: Flack x determined using 1854 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
8 restraints | Absolute 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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1B | 0.2546 (3) | 0.9044 (3) | 0.00091 (17) | 0.0801 (11) | |
H1OB | 0.267 | 0.8579 | 0.0206 | 0.12* | |
O2B | 0.4526 (3) | 0.7815 (3) | 0.00546 (13) | 0.0670 (10) | |
O3B | 0.4107 (4) | 0.6226 (4) | −0.0546 (2) | 0.1042 (16) | |
O4B | 0.7683 (2) | 0.7362 (3) | −0.07619 (14) | 0.0669 (9) | |
H4OB | 0.814 | 0.7762 | −0.0666 | 0.1* | |
O1A | 0.8534 (3) | 0.8191 (3) | 0.77682 (17) | 0.0758 (10) | |
H1OA | 0.9154 | 0.8296 | 0.7845 | 0.114* | |
O2A | 0.9696 (3) | 1.0156 (3) | 0.76596 (15) | 0.0672 (9) | |
O4A | 0.9420 (3) | 1.3257 (3) | 0.68883 (15) | 0.0705 (10) | |
H4OA | 0.911 | 1.3691 | 0.7054 | 0.106* | |
O3A | 1.0897 (5) | 0.9936 (5) | 0.6846 (2) | 0.1146 (17) | |
C12A | 0.8182 (4) | 1.0822 (4) | 0.73229 (19) | 0.0557 (11) | |
N1A | 0.7502 (4) | 1.3378 (3) | 0.72979 (18) | 0.0708 (12) | |
C19B | 1.0429 (5) | 1.0706 (7) | −0.1035 (4) | 0.109 (3) | |
H19A | 1.037 | 1.0696 | −0.1398 | 0.13* | |
H19B | 1.0884 | 1.1236 | −0.09 | 0.13* | |
C18B | 0.9463 (7) | 1.0394 (7) | −0.0730 (4) | 0.119 (3) | |
H18B | 0.9388 | 1.0746 | −0.0408 | 0.142* | |
C17B | 0.8476 (5) | 1.0179 (6) | −0.0984 (3) | 0.097 (2) | |
H17A | 0.8634 | 1.0002 | −0.133 | 0.116* | |
H17B | 0.8054 | 1.0797 | −0.0989 | 0.116* | |
N1B | 0.7834 (4) | 0.9358 (4) | −0.07652 (19) | 0.0750 (13) | |
C9B | 0.7061 (4) | 0.8938 (5) | −0.1122 (2) | 0.0686 (14) | |
H9B | 0.7451 | 0.8778 | −0.143 | 0.082* | |
C10B | 0.6132 (4) | 0.9638 (6) | −0.1273 (2) | 0.0789 (17) | |
H10A | 0.6382 | 1.0338 | −0.1277 | 0.095* | |
H10B | 0.5915 | 0.9466 | −0.1612 | 0.095* | |
C11B | 0.5170 (4) | 0.9576 (5) | −0.0934 (2) | 0.0647 (13) | |
C12B | 0.5182 (4) | 0.8850 (4) | −0.05664 (19) | 0.0605 (12) | |
C4B | 0.4323 (4) | 0.8633 (4) | −0.02585 (19) | 0.0588 (12) | |
C3B | 0.3410 (4) | 0.9198 (5) | −0.0292 (2) | 0.0676 (14) | |
C5B | 0.5429 (4) | 0.7298 (4) | −0.01796 (18) | 0.0622 (12) | |
H5B | 0.5851 | 0.6939 | 0.0074 | 0.075* | |
C6B | 0.5002 (4) | 0.6551 (5) | −0.0567 (2) | 0.0701 (14) | |
C7B | 0.5751 (5) | 0.6276 (5) | −0.0984 (2) | 0.0784 (16) | |
H7B1 | 0.5397 | 0.5831 | −0.1221 | 0.094* | |
H7B2 | 0.6359 | 0.5915 | −0.0848 | 0.094* | |
C8B | 0.6122 (5) | 0.7241 (5) | −0.1250 (2) | 0.0762 (16) | |
H8B1 | 0.6576 | 0.7059 | −0.153 | 0.091* | |
H8B2 | 0.5513 | 0.7606 | −0.1381 | 0.091* | |
C14B | 0.6727 (4) | 0.7921 (4) | −0.08904 (18) | 0.0615 (13) | |
C20B | 1.0388 (6) | 0.9724 (7) | −0.0768 (4) | 0.106 (2) | |
H20A | 1.0317 | 0.911 | −0.0969 | 0.128* | |
H20B | 1.0829 | 0.9649 | −0.0472 | 0.128* | |
C16B | 0.7337 (5) | 0.9643 (5) | −0.0285 (2) | 0.0738 (15) | |
H16A | 0.6813 | 1.0172 | −0.0342 | 0.089* | |
H16B | 0.7873 | 0.9913 | −0.0059 | 0.089* | |
C15B | 0.6805 (4) | 0.8719 (5) | −0.00433 (19) | 0.0663 (13) | |
H15A | 0.6382 | 0.8939 | 0.0241 | 0.08* | |
H15B | 0.7344 | 0.8253 | 0.0079 | 0.08* | |
C13B | 0.6087 (4) | 0.8161 (4) | −0.04238 (17) | 0.0572 (12) | |
C1B | 0.4239 (4) | 1.0143 (5) | −0.0972 (2) | 0.0757 (16) | |
H1B | 0.4183 | 1.0646 | −0.1217 | 0.091* | |
C2B | 0.3389 (4) | 0.9965 (5) | −0.0648 (2) | 0.0752 (16) | |
H2B | 0.2789 | 1.0375 | −0.0673 | 0.09* | |
C3A | 0.8106 (4) | 0.9058 (4) | 0.75699 (19) | 0.0611 (12) | |
C4A | 0.8653 (4) | 0.9970 (4) | 0.75256 (19) | 0.0567 (12) | |
C11A | 0.7171 (4) | 1.0823 (4) | 0.7127 (2) | 0.0615 (12) | |
C10A | 0.6817 (5) | 1.1772 (4) | 0.6849 (2) | 0.0736 (15) | |
H10C | 0.6146 | 1.1997 | 0.6989 | 0.088* | |
H10D | 0.6693 | 1.1594 | 0.65 | 0.088* | |
C9A | 0.7610 (4) | 1.2671 (4) | 0.6868 (2) | 0.0687 (14) | |
H9A | 0.7492 | 1.3075 | 0.6563 | 0.082* | |
C17A | 0.6514 (5) | 1.3991 (5) | 0.7290 (3) | 0.0891 (19) | |
H17C | 0.5948 | 1.3601 | 0.7445 | 0.107* | |
H17D | 0.6314 | 1.4119 | 0.6944 | 0.107* | |
C18A | 0.6627 (6) | 1.4996 (6) | 0.7559 (3) | 0.099 (2) | |
H18A | 0.6787 | 1.496 | 0.7918 | 0.118* | |
C19A | 0.5942 (5) | 1.5845 (5) | 0.7396 (3) | 0.0902 (19) | |
H19C | 0.5457 | 1.5722 | 0.7121 | 0.108* | |
H19D | 0.5681 | 1.6309 | 0.7652 | 0.108* | |
C5A | 0.9985 (4) | 1.1077 (4) | 0.7380 (2) | 0.0609 (12) | |
H5A | 1.0518 | 1.1467 | 0.7567 | 0.073* | |
C13A | 0.8951 (4) | 1.1696 (4) | 0.73411 (19) | 0.0566 (11) | |
C1A | 0.6618 (4) | 0.9901 (4) | 0.7174 (2) | 0.0716 (14) | |
H1A | 0.5926 | 0.9858 | 0.7055 | 0.086* | |
C2A | 0.7072 (4) | 0.9063 (4) | 0.7391 (2) | 0.0676 (14) | |
H2A | 0.6671 | 0.847 | 0.742 | 0.081* | |
C20A | 0.7084 (6) | 1.5861 (6) | 0.7285 (5) | 0.127 (3) | |
H20C | 0.7301 | 1.5749 | 0.694 | 0.153* | |
H20D | 0.7525 | 1.6335 | 0.747 | 0.153* | |
C16A | 0.7654 (5) | 1.2877 (5) | 0.7778 (2) | 0.0714 (14) | |
H16C | 0.7101 | 1.2371 | 0.7827 | 0.086* | |
H16D | 0.7597 | 1.3376 | 0.8045 | 0.086* | |
C15A | 0.8740 (4) | 1.2360 (4) | 0.78032 (19) | 0.0636 (12) | |
H15C | 0.8775 | 1.1939 | 0.8102 | 0.076* | |
H15D | 0.9288 | 1.2877 | 0.7828 | 0.076* | |
C14A | 0.8783 (4) | 1.2349 (4) | 0.6864 (2) | 0.0615 (12) | |
C8A | 0.9115 (5) | 1.1791 (5) | 0.6400 (2) | 0.0744 (15) | |
H8A1 | 0.9036 | 1.2235 | 0.6112 | 0.089* | |
H8A2 | 0.8659 | 1.1203 | 0.6352 | 0.089* | |
C7A | 1.0276 (6) | 1.1436 (5) | 0.6439 (2) | 0.0846 (19) | |
H7A1 | 1.0473 | 1.1087 | 0.6132 | 0.101* | |
H7A2 | 1.0733 | 1.2027 | 0.6475 | 0.101* | |
C6A | 1.0445 (5) | 1.0739 (5) | 0.6873 (2) | 0.0734 (15) | |
C5S | 0.965 (4) | 0.343 (2) | 0.9437 (12) | 0.24 (3) | 0.5 |
H5S1 | 1.0148 | 0.3627 | 0.9184 | 0.364* | 0.5 |
H5S2 | 0.9716 | 0.3864 | 0.9723 | 0.364* | 0.5 |
H5S3 | 0.9786 | 0.2733 | 0.9535 | 0.364* | 0.5 |
C7S | 0.664 (3) | 0.314 (2) | 0.9142 (10) | 0.184 (14) | 0.5 |
H7S1 | 0.6722 | 0.2465 | 0.9001 | 0.221* | 0.5 |
H7S2 | 0.6717 | 0.3614 | 0.8863 | 0.221* | 0.5 |
O2S | 0.755 (4) | 0.3299 (18) | 0.9445 (11) | 0.263 (17) | 0.5 |
C3S | 1.153 (3) | 0.343 (2) | 0.9293 (10) | 0.198 (17) | 0.5 |
H3S1 | 1.1759 | 0.4007 | 0.9496 | 0.238* | 0.5 |
H3S2 | 1.1514 | 0.2842 | 0.9511 | 0.238* | 0.5 |
C6S | 0.856 (4) | 0.350 (2) | 0.9234 (10) | 0.185 (16) | 0.5 |
H6S1 | 0.8511 | 0.4202 | 0.9118 | 0.222* | 0.5 |
H6S2 | 0.858 | 0.3088 | 0.8933 | 0.222* | 0.5 |
C1S | 1.447 (4) | 0.320 (2) | 0.9016 (12) | 0.22 (2) | 0.5 |
H1S1 | 1.4911 | 0.3358 | 0.93 | 0.334* | 0.5 |
H1S2 | 1.4587 | 0.2511 | 0.8914 | 0.334* | 0.5 |
H1S3 | 1.4649 | 0.3654 | 0.8744 | 0.334* | 0.5 |
C2S | 1.334 (4) | 0.335 (3) | 0.9153 (15) | 0.29 (4) | 0.5 |
H2S1 | 1.3266 | 0.2918 | 0.9448 | 0.353* | 0.5 |
H2S2 | 1.3327 | 0.4039 | 0.9281 | 0.353* | 0.5 |
C8S | 0.555 (4) | 0.322 (2) | 0.9300 (13) | 0.221 (19) | 0.5 |
H8S1 | 0.5093 | 0.3078 | 0.902 | 0.332* | 0.5 |
H8S2 | 0.5419 | 0.2734 | 0.9562 | 0.332* | 0.5 |
H8S3 | 0.5414 | 0.3895 | 0.9422 | 0.332* | 0.5 |
O1S | 1.233 (4) | 0.326 (2) | 0.8929 (11) | 0.38 (3) | 0.5 |
C4S | 1.043 (4) | 0.364 (2) | 0.9125 (16) | 0.32 (4) | 0.5 |
H4S1 | 0.9984 | 0.374 | 0.9413 | 0.487* | 0.5 |
H4S2 | 1.0419 | 0.424 | 0.892 | 0.487* | 0.5 |
H4S3 | 1.0173 | 0.3068 | 0.8935 | 0.487* | 0.5 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1B | 0.0473 (18) | 0.094 (3) | 0.099 (3) | 0.0078 (19) | 0.016 (2) | 0.016 (2) |
O2B | 0.0496 (17) | 0.083 (3) | 0.068 (2) | 0.0083 (17) | 0.0125 (16) | 0.0143 (19) |
O3B | 0.070 (3) | 0.120 (4) | 0.123 (4) | −0.033 (3) | 0.011 (3) | −0.011 (3) |
O4B | 0.0438 (17) | 0.090 (3) | 0.066 (2) | 0.0082 (17) | 0.0036 (15) | −0.0003 (19) |
O1A | 0.078 (2) | 0.0539 (19) | 0.095 (3) | 0.0006 (18) | 0.002 (2) | 0.013 (2) |
O2A | 0.0568 (19) | 0.0612 (19) | 0.084 (2) | 0.0008 (16) | −0.0116 (17) | 0.0110 (18) |
O4A | 0.080 (2) | 0.0555 (19) | 0.076 (2) | −0.0135 (19) | −0.0015 (19) | 0.0051 (18) |
O3A | 0.117 (4) | 0.114 (4) | 0.113 (4) | 0.046 (3) | 0.009 (3) | −0.018 (3) |
C12A | 0.052 (3) | 0.054 (3) | 0.061 (3) | −0.003 (2) | −0.003 (2) | 0.002 (2) |
N1A | 0.072 (3) | 0.060 (2) | 0.080 (3) | 0.010 (2) | −0.016 (2) | 0.000 (2) |
C19B | 0.065 (4) | 0.121 (6) | 0.140 (7) | −0.027 (4) | −0.001 (4) | 0.029 (5) |
C18B | 0.086 (5) | 0.121 (7) | 0.149 (8) | −0.017 (5) | 0.007 (5) | 0.016 (6) |
C17B | 0.057 (3) | 0.108 (5) | 0.126 (6) | −0.004 (3) | 0.006 (3) | 0.036 (5) |
N1B | 0.057 (2) | 0.090 (3) | 0.078 (3) | −0.007 (2) | 0.006 (2) | 0.012 (3) |
C9B | 0.052 (3) | 0.094 (4) | 0.060 (3) | 0.002 (3) | 0.007 (2) | 0.009 (3) |
C10B | 0.058 (3) | 0.110 (5) | 0.069 (3) | 0.001 (3) | 0.005 (3) | 0.021 (3) |
C11B | 0.052 (3) | 0.084 (4) | 0.058 (3) | 0.002 (2) | −0.002 (2) | 0.014 (3) |
C12B | 0.044 (2) | 0.078 (3) | 0.059 (3) | 0.003 (2) | −0.003 (2) | 0.004 (3) |
C4B | 0.046 (2) | 0.072 (3) | 0.059 (3) | 0.001 (2) | 0.003 (2) | 0.007 (2) |
C3B | 0.042 (3) | 0.087 (4) | 0.074 (3) | 0.003 (3) | 0.005 (2) | 0.004 (3) |
C5B | 0.045 (2) | 0.080 (3) | 0.061 (3) | 0.009 (2) | 0.003 (2) | 0.009 (3) |
C6B | 0.060 (3) | 0.073 (3) | 0.078 (3) | −0.001 (3) | −0.003 (3) | 0.006 (3) |
C7B | 0.063 (3) | 0.091 (4) | 0.082 (4) | 0.002 (3) | −0.010 (3) | −0.019 (3) |
C8B | 0.065 (3) | 0.101 (4) | 0.062 (3) | 0.003 (3) | 0.000 (2) | −0.013 (3) |
C14B | 0.042 (2) | 0.086 (4) | 0.056 (3) | 0.005 (2) | 0.002 (2) | 0.001 (3) |
C20B | 0.077 (4) | 0.106 (5) | 0.136 (6) | −0.004 (4) | −0.022 (4) | 0.029 (5) |
C16B | 0.058 (3) | 0.081 (4) | 0.082 (4) | −0.002 (3) | −0.009 (3) | 0.004 (3) |
C15B | 0.054 (3) | 0.089 (4) | 0.057 (3) | 0.002 (3) | −0.004 (2) | 0.000 (3) |
C13B | 0.044 (2) | 0.075 (3) | 0.053 (2) | 0.004 (2) | −0.0015 (19) | 0.004 (2) |
C1B | 0.059 (3) | 0.090 (4) | 0.078 (3) | 0.011 (3) | −0.006 (3) | 0.016 (3) |
C2B | 0.050 (3) | 0.089 (4) | 0.087 (4) | 0.012 (3) | −0.002 (3) | 0.013 (3) |
C3A | 0.064 (3) | 0.058 (3) | 0.062 (3) | 0.000 (2) | 0.005 (2) | 0.003 (2) |
C4A | 0.052 (3) | 0.055 (3) | 0.063 (3) | −0.003 (2) | −0.002 (2) | 0.002 (2) |
C11A | 0.056 (3) | 0.062 (3) | 0.066 (3) | −0.003 (2) | −0.009 (2) | 0.001 (2) |
C10A | 0.065 (3) | 0.072 (3) | 0.084 (4) | −0.004 (3) | −0.025 (3) | 0.006 (3) |
C9A | 0.072 (3) | 0.062 (3) | 0.072 (3) | 0.000 (3) | −0.019 (3) | 0.006 (3) |
C17A | 0.077 (4) | 0.069 (4) | 0.121 (5) | 0.012 (3) | −0.018 (4) | −0.001 (4) |
C18A | 0.084 (4) | 0.084 (5) | 0.128 (6) | 0.017 (4) | −0.024 (4) | 0.002 (4) |
C19A | 0.072 (4) | 0.081 (4) | 0.118 (5) | 0.017 (3) | −0.014 (4) | −0.017 (4) |
C5A | 0.054 (3) | 0.056 (3) | 0.072 (3) | −0.007 (2) | −0.004 (2) | 0.001 (2) |
C13A | 0.056 (3) | 0.054 (3) | 0.060 (3) | −0.003 (2) | −0.007 (2) | 0.005 (2) |
C1A | 0.057 (3) | 0.074 (3) | 0.084 (4) | −0.007 (3) | −0.010 (3) | −0.005 (3) |
C2A | 0.063 (3) | 0.056 (3) | 0.083 (3) | −0.012 (3) | 0.006 (3) | 0.001 (3) |
C20A | 0.079 (5) | 0.094 (5) | 0.209 (11) | 0.010 (4) | −0.021 (6) | −0.018 (6) |
C16A | 0.068 (3) | 0.072 (3) | 0.074 (3) | 0.003 (3) | −0.001 (3) | −0.002 (3) |
C15A | 0.068 (3) | 0.064 (3) | 0.059 (3) | 0.002 (2) | −0.005 (2) | −0.002 (2) |
C14A | 0.071 (3) | 0.052 (3) | 0.061 (3) | −0.008 (2) | −0.004 (2) | 0.003 (2) |
C8A | 0.095 (4) | 0.071 (3) | 0.057 (3) | −0.012 (3) | 0.002 (3) | 0.002 (3) |
C7A | 0.099 (5) | 0.070 (4) | 0.085 (4) | −0.019 (3) | 0.031 (4) | −0.012 (3) |
C6A | 0.059 (3) | 0.073 (4) | 0.088 (4) | −0.002 (3) | 0.005 (3) | −0.011 (3) |
C5S | 0.51 (8) | 0.081 (15) | 0.14 (2) | 0.05 (3) | 0.00 (4) | 0.043 (15) |
C7S | 0.31 (4) | 0.13 (2) | 0.111 (17) | −0.03 (3) | 0.06 (3) | 0.009 (15) |
O2S | 0.48 (6) | 0.127 (15) | 0.18 (2) | 0.00 (3) | −0.01 (3) | −0.003 (15) |
C3S | 0.37 (5) | 0.123 (18) | 0.104 (15) | −0.10 (3) | −0.05 (3) | −0.008 (14) |
C6S | 0.32 (5) | 0.115 (18) | 0.124 (18) | −0.07 (2) | −0.05 (2) | 0.058 (15) |
C1S | 0.41 (7) | 0.110 (17) | 0.15 (2) | −0.08 (3) | −0.05 (3) | 0.049 (17) |
C2S | 0.52 (9) | 0.14 (2) | 0.23 (4) | −0.14 (5) | 0.20 (6) | −0.06 (3) |
C8S | 0.39 (6) | 0.105 (17) | 0.17 (3) | 0.06 (3) | 0.06 (4) | 0.041 (19) |
O1S | 0.76 (10) | 0.24 (3) | 0.15 (2) | −0.21 (5) | −0.06 (4) | 0.11 (2) |
C4S | 0.61 (10) | 0.090 (16) | 0.27 (5) | −0.09 (3) | −0.26 (6) | 0.12 (2) |
Geometric parameters (Å, º) top
O1B—C3B | 1.367 (6) | C3A—C2A | 1.388 (8) |
O1B—H1OB | 0.82 | C11A—C1A | 1.401 (8) |
O2B—C4B | 1.382 (6) | C11A—C10A | 1.515 (8) |
O2B—C5B | 1.464 (6) | C10A—C9A | 1.545 (8) |
O3B—C6B | 1.207 (7) | C10A—H10C | 0.97 |
O4B—C14B | 1.451 (6) | C10A—H10D | 0.97 |
O4B—H4OB | 0.82 | C9A—C14A | 1.537 (8) |
O1A—C3A | 1.364 (6) | C9A—H9A | 0.98 |
O1A—H1OA | 0.82 | C17A—C18A | 1.507 (10) |
O2A—C4A | 1.384 (6) | C17A—H17C | 0.97 |
O2A—C5A | 1.466 (6) | C17A—H17D | 0.97 |
O4A—C14A | 1.438 (6) | C18A—C20A | 1.467 (12) |
O4A—H4OA | 0.82 | C18A—C19A | 1.474 (9) |
O3A—C6A | 1.199 (8) | C18A—H18A | 0.98 |
C12A—C4A | 1.375 (7) | C19A—C20A | 1.469 (11) |
C12A—C11A | 1.377 (7) | C19A—H19C | 0.97 |
C12A—C13A | 1.501 (7) | C19A—H19D | 0.97 |
N1A—C16A | 1.451 (7) | C5A—C6A | 1.536 (8) |
N1A—C9A | 1.481 (8) | C5A—C13A | 1.537 (7) |
N1A—C17A | 1.481 (8) | C5A—H5A | 0.98 |
C19B—C20B | 1.471 (11) | C13A—C15A | 1.532 (8) |
C19B—C18B | 1.519 (11) | C13A—C14A | 1.548 (7) |
C19B—H19A | 0.97 | C1A—C2A | 1.367 (8) |
C19B—H19B | 0.97 | C1A—H1A | 0.93 |
C18B—C17B | 1.443 (11) | C2A—H2A | 0.93 |
C18B—C20B | 1.463 (12) | C20A—H20C | 0.97 |
C18B—H18B | 0.98 | C20A—H20D | 0.97 |
C17B—N1B | 1.468 (8) | C16A—C15A | 1.529 (8) |
C17B—H17A | 0.97 | C16A—H16C | 0.97 |
C17B—H17B | 0.97 | C16A—H16D | 0.97 |
N1B—C9B | 1.468 (7) | C15A—H15C | 0.97 |
N1B—C16B | 1.474 (8) | C15A—H15D | 0.97 |
C9B—C14B | 1.529 (8) | C14A—C8A | 1.496 (8) |
C9B—C10B | 1.541 (8) | C8A—C7A | 1.538 (10) |
C9B—H9B | 0.98 | C8A—H8A1 | 0.97 |
C10B—C11B | 1.514 (7) | C8A—H8A2 | 0.97 |
C10B—H10A | 0.97 | C7A—C6A | 1.490 (10) |
C10B—H10B | 0.97 | C7A—H7A1 | 0.97 |
C11B—C12B | 1.366 (8) | C7A—H7A2 | 0.97 |
C11B—C1B | 1.393 (8) | C5S—C6S | 1.47 (3) |
C12B—C4B | 1.388 (7) | C5S—H5S1 | 0.96 |
C12B—C13B | 1.504 (7) | C5S—H5S2 | 0.96 |
C4B—C3B | 1.372 (7) | C5S—H5S3 | 0.96 |
C3B—C2B | 1.385 (8) | C7S—O2S | 1.42 (2) |
C5B—C6B | 1.521 (8) | C7S—C8S | 1.44 (2) |
C5B—C13B | 1.546 (7) | C7S—H7S1 | 0.97 |
C5B—H5B | 0.98 | C7S—H7S2 | 0.97 |
C6B—C7B | 1.501 (9) | O2S—C6S | 1.42 (2) |
C7B—C8B | 1.523 (10) | C3S—O1S | 1.42 (3) |
C7B—H7B1 | 0.97 | C3S—C4S | 1.49 (3) |
C7B—H7B2 | 0.97 | C3S—H3S1 | 0.97 |
C8B—C14B | 1.514 (8) | C3S—H3S2 | 0.97 |
C8B—H8B1 | 0.97 | C6S—H6S1 | 0.97 |
C8B—H8B2 | 0.97 | C6S—H6S2 | 0.97 |
C14B—C13B | 1.515 (7) | C1S—C2S | 1.49 (3) |
C20B—H20A | 0.97 | C1S—H1S1 | 0.96 |
C20B—H20B | 0.97 | C1S—H1S2 | 0.96 |
C16B—C15B | 1.527 (8) | C1S—H1S3 | 0.96 |
C16B—H16A | 0.97 | C2S—O1S | 1.40 (3) |
C16B—H16B | 0.97 | C2S—H2S1 | 0.97 |
C15B—C13B | 1.543 (7) | C2S—H2S2 | 0.97 |
C15B—H15A | 0.97 | C8S—H8S1 | 0.96 |
C15B—H15B | 0.97 | C8S—H8S2 | 0.96 |
C1B—C2B | 1.395 (8) | C8S—H8S3 | 0.96 |
C1B—H1B | 0.93 | C4S—H4S1 | 0.96 |
C2B—H2B | 0.93 | C4S—H4S2 | 0.96 |
C3A—C4A | 1.385 (7) | C4S—H4S3 | 0.96 |
| | | |
C3B—O1B—H1OB | 109.5 | N1A—C9A—C10A | 116.3 (5) |
C4B—O2B—C5B | 104.2 (4) | C14A—C9A—C10A | 114.3 (5) |
C14B—O4B—H4OB | 109.5 | N1A—C9A—H9A | 106.7 |
C3A—O1A—H1OA | 109.5 | C14A—C9A—H9A | 106.7 |
C4A—O2A—C5A | 104.4 (4) | C10A—C9A—H9A | 106.7 |
C14A—O4A—H4OA | 109.5 | N1A—C17A—C18A | 112.8 (5) |
C4A—C12A—C11A | 123.3 (5) | N1A—C17A—H17C | 109 |
C4A—C12A—C13A | 109.2 (4) | C18A—C17A—H17C | 109 |
C11A—C12A—C13A | 127.5 (4) | N1A—C17A—H17D | 109 |
C16A—N1A—C9A | 112.8 (4) | C18A—C17A—H17D | 109 |
C16A—N1A—C17A | 111.7 (5) | H17C—C17A—H17D | 107.8 |
C9A—N1A—C17A | 113.9 (5) | C20A—C18A—C19A | 59.9 (5) |
C20B—C19B—C18B | 58.5 (5) | C20A—C18A—C17A | 118.4 (8) |
C20B—C19B—H19A | 117.9 | C19A—C18A—C17A | 117.7 (6) |
C18B—C19B—H19A | 117.9 | C20A—C18A—H18A | 116.3 |
C20B—C19B—H19B | 117.9 | C19A—C18A—H18A | 116.3 |
C18B—C19B—H19B | 117.9 | C17A—C18A—H18A | 116.3 |
H19A—C19B—H19B | 115.1 | C20A—C19A—C18A | 59.8 (5) |
C17B—C18B—C20B | 122.5 (9) | C20A—C19A—H19C | 117.8 |
C17B—C18B—C19B | 119.5 (9) | C18A—C19A—H19C | 117.8 |
C20B—C18B—C19B | 59.1 (6) | C20A—C19A—H19D | 117.8 |
C17B—C18B—H18B | 114.8 | C18A—C19A—H19D | 117.8 |
C20B—C18B—H18B | 114.8 | H19C—C19A—H19D | 114.9 |
C19B—C18B—H18B | 114.8 | O2A—C5A—C6A | 107.6 (4) |
C18B—C17B—N1B | 115.6 (7) | O2A—C5A—C13A | 105.0 (4) |
C18B—C17B—H17A | 108.4 | C6A—C5A—C13A | 114.4 (5) |
N1B—C17B—H17A | 108.4 | O2A—C5A—H5A | 109.9 |
C18B—C17B—H17B | 108.4 | C6A—C5A—H5A | 109.9 |
N1B—C17B—H17B | 108.4 | C13A—C5A—H5A | 109.9 |
H17A—C17B—H17B | 107.4 | C12A—C13A—C15A | 110.3 (4) |
C17B—N1B—C9B | 112.5 (5) | C12A—C13A—C5A | 98.4 (4) |
C17B—N1B—C16B | 113.2 (6) | C15A—C13A—C5A | 113.1 (4) |
C9B—N1B—C16B | 112.1 (4) | C12A—C13A—C14A | 107.9 (4) |
N1B—C9B—C14B | 104.4 (4) | C15A—C13A—C14A | 108.8 (4) |
N1B—C9B—C10B | 116.8 (5) | C5A—C13A—C14A | 117.5 (4) |
C14B—C9B—C10B | 114.6 (4) | C2A—C1A—C11A | 121.6 (5) |
N1B—C9B—H9B | 106.8 | C2A—C1A—H1A | 119.2 |
C14B—C9B—H9B | 106.8 | C11A—C1A—H1A | 119.2 |
C10B—C9B—H9B | 106.8 | C1A—C2A—C3A | 122.8 (5) |
C11B—C10B—C9B | 114.8 (5) | C1A—C2A—H2A | 118.6 |
C11B—C10B—H10A | 108.6 | C3A—C2A—H2A | 118.6 |
C9B—C10B—H10A | 108.6 | C18A—C20A—C19A | 60.3 (6) |
C11B—C10B—H10B | 108.6 | C18A—C20A—H20C | 117.7 |
C9B—C10B—H10B | 108.6 | C19A—C20A—H20C | 117.7 |
H10A—C10B—H10B | 107.5 | C18A—C20A—H20D | 117.7 |
C12B—C11B—C1B | 115.7 (5) | C19A—C20A—H20D | 117.7 |
C12B—C11B—C10B | 117.2 (5) | H20C—C20A—H20D | 114.9 |
C1B—C11B—C10B | 127.0 (5) | N1A—C16A—C15A | 110.9 (5) |
C11B—C12B—C4B | 124.0 (5) | N1A—C16A—H16C | 109.4 |
C11B—C12B—C13B | 127.5 (4) | C15A—C16A—H16C | 109.4 |
C4B—C12B—C13B | 108.5 (4) | N1A—C16A—H16D | 109.4 |
C3B—C4B—O2B | 127.8 (4) | C15A—C16A—H16D | 109.4 |
C3B—C4B—C12B | 120.3 (5) | H16C—C16A—H16D | 108 |
O2B—C4B—C12B | 111.9 (4) | C16A—C15A—C13A | 111.8 (4) |
O1B—C3B—C4B | 123.4 (5) | C16A—C15A—H15C | 109.2 |
O1B—C3B—C2B | 119.7 (5) | C13A—C15A—H15C | 109.2 |
C4B—C3B—C2B | 116.9 (5) | C16A—C15A—H15D | 109.2 |
O2B—C5B—C6B | 108.3 (4) | C13A—C15A—H15D | 109.2 |
O2B—C5B—C13B | 104.9 (4) | H15C—C15A—H15D | 107.9 |
C6B—C5B—C13B | 112.0 (4) | O4A—C14A—C8A | 106.6 (4) |
O2B—C5B—H5B | 110.5 | O4A—C14A—C9A | 108.0 (4) |
C6B—C5B—H5B | 110.5 | C8A—C14A—C9A | 114.1 (5) |
C13B—C5B—H5B | 110.5 | O4A—C14A—C13A | 110.1 (4) |
O3B—C6B—C7B | 122.5 (6) | C8A—C14A—C13A | 111.7 (4) |
O3B—C6B—C5B | 121.7 (6) | C9A—C14A—C13A | 106.1 (4) |
C7B—C6B—C5B | 115.8 (5) | C14A—C8A—C7A | 111.0 (5) |
C6B—C7B—C8B | 109.8 (5) | C14A—C8A—H8A1 | 109.4 |
C6B—C7B—H7B1 | 109.7 | C7A—C8A—H8A1 | 109.4 |
C8B—C7B—H7B1 | 109.7 | C14A—C8A—H8A2 | 109.4 |
C6B—C7B—H7B2 | 109.7 | C7A—C8A—H8A2 | 109.4 |
C8B—C7B—H7B2 | 109.7 | H8A1—C8A—H8A2 | 108 |
H7B1—C7B—H7B2 | 108.2 | C6A—C7A—C8A | 111.9 (5) |
C14B—C8B—C7B | 110.4 (5) | C6A—C7A—H7A1 | 109.2 |
C14B—C8B—H8B1 | 109.6 | C8A—C7A—H7A1 | 109.2 |
C7B—C8B—H8B1 | 109.6 | C6A—C7A—H7A2 | 109.2 |
C14B—C8B—H8B2 | 109.6 | C8A—C7A—H7A2 | 109.2 |
C7B—C8B—H8B2 | 109.6 | H7A1—C7A—H7A2 | 107.9 |
H8B1—C8B—H8B2 | 108.1 | O3A—C6A—C7A | 124.0 (6) |
O4B—C14B—C8B | 105.6 (5) | O3A—C6A—C5A | 119.1 (6) |
O4B—C14B—C13B | 110.7 (4) | C7A—C6A—C5A | 116.9 (5) |
C8B—C14B—C13B | 111.9 (4) | C6S—C5S—H5S1 | 109.5 |
O4B—C14B—C9B | 107.9 (4) | C6S—C5S—H5S2 | 109.5 |
C8B—C14B—C9B | 113.4 (5) | H5S1—C5S—H5S2 | 109.5 |
C13B—C14B—C9B | 107.3 (5) | C6S—C5S—H5S3 | 109.5 |
C18B—C20B—C19B | 62.3 (6) | H5S1—C5S—H5S3 | 109.5 |
C18B—C20B—H20A | 117.5 | H5S2—C5S—H5S3 | 109.5 |
C19B—C20B—H20A | 117.5 | O2S—C7S—C8S | 126 (3) |
C18B—C20B—H20B | 117.5 | O2S—C7S—H7S1 | 105.7 |
C19B—C20B—H20B | 117.5 | C8S—C7S—H7S1 | 105.7 |
H20A—C20B—H20B | 114.6 | O2S—C7S—H7S2 | 105.7 |
N1B—C16B—C15B | 110.5 (5) | C8S—C7S—H7S2 | 105.7 |
N1B—C16B—H16A | 109.5 | H7S1—C7S—H7S2 | 106.1 |
C15B—C16B—H16A | 109.5 | C6S—O2S—C7S | 122 (3) |
N1B—C16B—H16B | 109.5 | O1S—C3S—C4S | 119 (3) |
C15B—C16B—H16B | 109.5 | O1S—C3S—H3S1 | 107.5 |
H16A—C16B—H16B | 108.1 | C4S—C3S—H3S1 | 107.5 |
C16B—C15B—C13B | 110.9 (4) | O1S—C3S—H3S2 | 107.5 |
C16B—C15B—H15A | 109.5 | C4S—C3S—H3S2 | 107.5 |
C13B—C15B—H15A | 109.5 | H3S1—C3S—H3S2 | 107 |
C16B—C15B—H15B | 109.5 | O2S—C6S—C5S | 132 (3) |
C13B—C15B—H15B | 109.5 | O2S—C6S—H6S1 | 104.1 |
H15A—C15B—H15B | 108 | C5S—C6S—H6S1 | 104.1 |
C12B—C13B—C14B | 108.7 (4) | O2S—C6S—H6S2 | 104.1 |
C12B—C13B—C15B | 109.0 (5) | C5S—C6S—H6S2 | 104.1 |
C14B—C13B—C15B | 109.0 (4) | H6S1—C6S—H6S2 | 105.5 |
C12B—C13B—C5B | 98.0 (4) | C2S—C1S—H1S1 | 109.5 |
C14B—C13B—C5B | 118.6 (5) | C2S—C1S—H1S2 | 109.5 |
C15B—C13B—C5B | 112.6 (4) | H1S1—C1S—H1S2 | 109.5 |
C11B—C1B—C2B | 120.8 (5) | C2S—C1S—H1S3 | 109.5 |
C11B—C1B—H1B | 119.6 | H1S1—C1S—H1S3 | 109.5 |
C2B—C1B—H1B | 119.6 | H1S2—C1S—H1S3 | 109.5 |
C3B—C2B—C1B | 122.1 (5) | O1S—C2S—C1S | 139 (4) |
C3B—C2B—H2B | 118.9 | O1S—C2S—H2S1 | 102.4 |
C1B—C2B—H2B | 118.9 | C1S—C2S—H2S1 | 102.4 |
O1A—C3A—C4A | 123.8 (5) | O1S—C2S—H2S2 | 102.4 |
O1A—C3A—C2A | 120.5 (5) | C1S—C2S—H2S2 | 102.4 |
C4A—C3A—C2A | 115.7 (5) | H2S1—C2S—H2S2 | 104.9 |
C12A—C4A—O2A | 111.6 (4) | C7S—C8S—H8S1 | 109.5 |
C12A—C4A—C3A | 121.3 (4) | C7S—C8S—H8S2 | 109.5 |
O2A—C4A—C3A | 127.0 (5) | H8S1—C8S—H8S2 | 109.5 |
C12A—C11A—C1A | 115.1 (5) | C7S—C8S—H8S3 | 109.5 |
C12A—C11A—C10A | 117.3 (5) | H8S1—C8S—H8S3 | 109.5 |
C1A—C11A—C10A | 127.3 (5) | H8S2—C8S—H8S3 | 109.5 |
C11A—C10A—C9A | 114.8 (4) | C2S—O1S—C3S | 110 (3) |
C11A—C10A—H10C | 108.6 | C3S—C4S—H4S1 | 109.5 |
C9A—C10A—H10C | 108.6 | C3S—C4S—H4S2 | 109.5 |
C11A—C10A—H10D | 108.6 | H4S1—C4S—H4S2 | 109.5 |
C9A—C10A—H10D | 108.6 | C3S—C4S—H4S3 | 109.5 |
H10C—C10A—H10D | 107.5 | H4S1—C4S—H4S3 | 109.5 |
N1A—C9A—C14A | 105.4 (4) | H4S2—C4S—H4S3 | 109.5 |
| | | |
C20B—C19B—C18B—C17B | −112.3 (10) | C11A—C12A—C4A—C3A | −3.6 (8) |
C20B—C18B—C17B—N1B | 74.3 (11) | C13A—C12A—C4A—C3A | 178.0 (5) |
N1B—C17B—C18B—C19B | 144.5 (8) | C5A—O2A—C4A—C12A | −18.4 (5) |
C9B—N1B—C17B—C18B | −160.0 (7) | C5A—O2A—C4A—C3A | 160.4 (5) |
C18B—C17B—N1B—C16B | 71.6 (8) | O1A—C3A—C4A—C12A | −179.9 (5) |
C17B—N1B—C9B—C14B | 163.3 (5) | C2A—C3A—C4A—C12A | 0.9 (7) |
C16B—N1B—C9B—C14B | −67.8 (6) | O1A—C3A—C4A—O2A | 1.4 (8) |
C17B—N1B—C9B—C10B | −69.1 (6) | C2A—C3A—C4A—O2A | −177.8 (5) |
C16B—N1B—C9B—C10B | 59.9 (6) | C4A—C12A—C11A—C1A | 3.6 (8) |
N1B—C9B—C10B—C11B | −88.3 (7) | C13A—C12A—C11A—C1A | −178.3 (5) |
C14B—C9B—C10B—C11B | 34.2 (8) | C4A—C12A—C11A—C10A | −171.3 (5) |
C9B—C10B—C11B—C12B | −6.2 (9) | C13A—C12A—C11A—C10A | 6.8 (8) |
C9B—C10B—C11B—C1B | 177.8 (6) | C12A—C11A—C10A—C9A | −5.9 (8) |
C1B—C11B—C12B—C4B | 3.0 (9) | C1A—C11A—C10A—C9A | 179.9 (6) |
C10B—C11B—C12B—C4B | −173.5 (6) | C16A—N1A—C9A—C14A | −67.0 (6) |
C1B—C11B—C12B—C13B | −177.2 (5) | C17A—N1A—C9A—C14A | 164.4 (5) |
C10B—C11B—C12B—C13B | 6.3 (9) | C16A—N1A—C9A—C10A | 60.8 (6) |
C5B—O2B—C4B—C3B | 161.0 (6) | C17A—N1A—C9A—C10A | −67.8 (6) |
C5B—O2B—C4B—C12B | −18.3 (6) | C11A—C10A—C9A—N1A | −88.3 (6) |
C11B—C12B—C4B—C3B | −3.9 (9) | C11A—C10A—C9A—C14A | 34.9 (8) |
C13B—C12B—C4B—C3B | 176.2 (5) | C16A—N1A—C17A—C18A | 77.9 (7) |
C11B—C12B—C4B—O2B | 175.5 (5) | C9A—N1A—C17A—C18A | −152.9 (6) |
C13B—C12B—C4B—O2B | −4.4 (6) | N1A—C17A—C18A—C20A | 83.8 (8) |
O2B—C4B—C3B—O1B | 2.6 (9) | N1A—C17A—C18A—C19A | 152.8 (7) |
C12B—C4B—C3B—O1B | −178.1 (5) | C17A—C18A—C19A—C20A | −108.4 (9) |
O2B—C4B—C3B—C2B | −178.0 (5) | C4A—O2A—C5A—C6A | −90.3 (5) |
C12B—C4B—C3B—C2B | 1.3 (8) | C4A—O2A—C5A—C13A | 32.0 (5) |
C4B—O2B—C5B—C6B | −86.7 (5) | C4A—C12A—C13A—C15A | −96.9 (5) |
C4B—O2B—C5B—C13B | 33.0 (5) | C11A—C12A—C13A—C15A | 84.8 (6) |
O2B—C5B—C6B—O3B | −22.4 (8) | C4A—C12A—C13A—C5A | 21.7 (5) |
C13B—C5B—C6B—O3B | −137.5 (6) | C11A—C12A—C13A—C5A | −156.6 (5) |
O2B—C5B—C6B—C7B | 155.6 (5) | C4A—C12A—C13A—C14A | 144.3 (4) |
C13B—C5B—C6B—C7B | 40.4 (7) | C11A—C12A—C13A—C14A | −34.0 (7) |
O3B—C6B—C7B—C8B | 121.9 (7) | O2A—C5A—C13A—C12A | −32.0 (5) |
C5B—C6B—C7B—C8B | −56.0 (7) | C6A—C5A—C13A—C12A | 85.8 (5) |
C6B—C7B—C8B—C14B | 62.2 (6) | O2A—C5A—C13A—C15A | 84.5 (5) |
C7B—C8B—C14B—O4B | 65.9 (5) | C6A—C5A—C13A—C15A | −157.8 (5) |
C7B—C8B—C14B—C13B | −54.6 (6) | O2A—C5A—C13A—C14A | −147.3 (4) |
C7B—C8B—C14B—C9B | −176.1 (4) | C6A—C5A—C13A—C14A | −29.5 (6) |
N1B—C9B—C14B—O4B | −50.1 (5) | C12A—C11A—C1A—C2A | −1.3 (9) |
C10B—C9B—C14B—O4B | −179.1 (5) | C10A—C11A—C1A—C2A | 173.0 (6) |
N1B—C9B—C14B—C8B | −166.8 (4) | C11A—C1A—C2A—C3A | −1.2 (10) |
C10B—C9B—C14B—C8B | 64.3 (6) | O1A—C3A—C2A—C1A | −177.8 (5) |
N1B—C9B—C14B—C13B | 69.1 (5) | C4A—C3A—C2A—C1A | 1.3 (8) |
C10B—C9B—C14B—C13B | −59.9 (6) | C17A—C18A—C20A—C19A | 107.4 (7) |
C17B—C18B—C20B—C19B | 107.4 (10) | C9A—N1A—C16A—C15A | 57.4 (6) |
C17B—N1B—C16B—C15B | −172.5 (5) | C17A—N1A—C16A—C15A | −172.9 (5) |
C9B—N1B—C16B—C15B | 58.9 (6) | N1A—C16A—C15A—C13A | −49.6 (6) |
N1B—C16B—C15B—C13B | −49.5 (6) | C12A—C13A—C15A—C16A | −64.8 (6) |
C11B—C12B—C13B—C14B | −32.5 (8) | C5A—C13A—C15A—C16A | −174.0 (4) |
C4B—C12B—C13B—C14B | 147.3 (5) | C14A—C13A—C15A—C16A | 53.4 (6) |
C11B—C12B—C13B—C15B | 86.2 (7) | N1A—C9A—C14A—O4A | −50.4 (5) |
C4B—C12B—C13B—C15B | −94.0 (5) | C10A—C9A—C14A—O4A | −179.4 (5) |
C11B—C12B—C13B—C5B | −156.5 (6) | N1A—C9A—C14A—C8A | −168.8 (4) |
C4B—C12B—C13B—C5B | 23.4 (5) | C10A—C9A—C14A—C8A | 62.3 (7) |
O4B—C14B—C13B—C12B | 172.9 (4) | N1A—C9A—C14A—C13A | 67.7 (5) |
C8B—C14B—C13B—C12B | −69.6 (6) | C10A—C9A—C14A—C13A | −61.3 (6) |
C9B—C14B—C13B—C12B | 55.4 (5) | C12A—C13A—C14A—O4A | 173.8 (4) |
O4B—C14B—C13B—C15B | 54.2 (6) | C15A—C13A—C14A—O4A | 54.1 (5) |
C8B—C14B—C13B—C15B | 171.8 (5) | C5A—C13A—C14A—O4A | −76.2 (6) |
C9B—C14B—C13B—C15B | −63.2 (5) | C12A—C13A—C14A—C8A | −67.9 (5) |
O4B—C14B—C13B—C5B | −76.4 (5) | C15A—C13A—C14A—C8A | 172.4 (5) |
C8B—C14B—C13B—C5B | 41.1 (6) | C5A—C13A—C14A—C8A | 42.1 (6) |
C9B—C14B—C13B—C5B | 166.1 (4) | C12A—C13A—C14A—C9A | 57.1 (5) |
C16B—C15B—C13B—C12B | −65.5 (5) | C15A—C13A—C14A—C9A | −62.6 (5) |
C16B—C15B—C13B—C14B | 53.0 (6) | C5A—C13A—C14A—C9A | 167.1 (4) |
C16B—C15B—C13B—C5B | −173.1 (4) | O4A—C14A—C8A—C7A | 64.4 (6) |
O2B—C5B—C13B—C12B | −33.8 (5) | C9A—C14A—C8A—C7A | −176.4 (5) |
C6B—C5B—C13B—C12B | 83.5 (5) | C13A—C14A—C8A—C7A | −56.0 (6) |
O2B—C5B—C13B—C14B | −150.2 (4) | C14A—C8A—C7A—C6A | 59.8 (7) |
C6B—C5B—C13B—C14B | −33.0 (6) | C8A—C7A—C6A—O3A | 131.0 (7) |
O2B—C5B—C13B—C15B | 80.8 (5) | C8A—C7A—C6A—C5A | −47.8 (7) |
C6B—C5B—C13B—C15B | −162.0 (4) | O2A—C5A—C6A—O3A | −29.9 (7) |
C12B—C11B—C1B—C2B | 0.3 (9) | C13A—C5A—C6A—O3A | −146.1 (6) |
C10B—C11B—C1B—C2B | 176.4 (6) | O2A—C5A—C6A—C7A | 149.1 (5) |
O1B—C3B—C2B—C1B | −178.6 (6) | C13A—C5A—C6A—C7A | 32.8 (7) |
C4B—C3B—C2B—C1B | 1.9 (9) | C8S—C7S—O2S—C6S | −161 (3) |
C11B—C1B—C2B—C3B | −2.8 (10) | C7S—O2S—C6S—C5S | −161 (4) |
C11A—C12A—C4A—O2A | 175.3 (5) | C1S—C2S—O1S—C3S | 175 (4) |
C13A—C12A—C4A—O2A | −3.1 (6) | C4S—C3S—O1S—C2S | 165 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1OA···O4Ai | 0.82 | 1.93 | 2.737 (5) | 167 |
O4A—H4OA···O2Aii | 0.82 | 2.56 | 2.982 (6) | 114 |
O1B—H1OB···O4Biii | 0.82 | 1.93 | 2.730 (6) | 166 |
O4B—H4OB···O2Biv | 0.82 | 2.51 | 3.000 (5) | 120 |
C20B—H20A···O4Av | 0.97 | 2.71 | 3.560 (11) | 146 |
C20B—H20B···O1Bvi | 0.97 | 2.64 | 3.533 (10) | 154 |
Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) −x+2, y+1/2, −z+3/2; (iii) x−1/2, −y+3/2, −z; (iv) x+1/2, −y+3/2, −z; (v) −x+2, y−1/2, −z+1/2; (vi) x+1, y, z. |