New solvates of the drug naltrexone: protonation, conformation and inter­play of synthons

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.

Computing details

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)

Crystal data

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) Å^3	Prism, colourless
Z = 4	0.22 × 0.18 × 0.10 mm
F(000) = 2376

Data collection

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

Refinement on F^2	Hydrogen site location: constr
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.052	w = 1/[σ^2(Fo^2) + (0.0843P)^2 + 0.2244P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1OA···O4A^i	0.82	1.90	2.710 (5)	168
O4A—H4OA···O2A^ii	0.82	2.43	2.904 (4)	118
O1B—H1OB···O4B^iii	0.82	1.92	2.728 (5)	170
O4B—H4OB···O2B^iv	0.82	2.39	2.942 (4)	126
O1C—H1OC···O4C^v	0.82	1.88	2.672 (6)	164
O4C—H4OC···O2C^vi	0.82	2.84	3.125 (4)	103
C8B—H8B2···O1S	0.97	2.54	3.395 (10)	147
C20B—H20E···O1B^vii	0.97	2.66	3.589 (15)	160
C18C—H18C···O3C^vi	0.98	2.63	3.501 (7)	148
C19A—H19D···Cg(A)C^viii	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.

(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)

Crystal data

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) Å^3	Needle, colourless
Z = 4	0.20 × 0.10 × 0.08 mm
F(000) = 1624

Data collection

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

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.065	w = 1/[σ^2(Fo^2) + (0.113P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1OA···O4A^i	0.82	1.93	2.737 (5)	167
O4A—H4OA···O2A^ii	0.82	2.56	2.982 (6)	114
O1B—H1OB···O4B^iii	0.82	1.93	2.730 (6)	166
O4B—H4OB···O2B^iv	0.82	2.51	3.000 (5)	120
C20B—H20A···O4A^v	0.97	2.71	3.560 (11)	146
C20B—H20B···O1B^vi	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.