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Acta Crystallographica Section E: Crystallographic Communications logoLink to Acta Crystallographica Section E: Crystallographic Communications
. 2015 Feb 18;71(Pt 3):275–277. doi: 10.1107/S2056989015001747

Crystal structure of (S)-2-[(3S,8S,9S,10R,13S,14S,17R)-3-hy­droxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetra­deca­hydro-1H-cyclo­penta[a]phenanthren-17-yl]-N-meth­oxy-N-methyl­pro­pan­amide (Fernholz Weinreb amide)

Elvar Ørn Viktorsson a, Ove Alexander Høgmoen Åstrand a, Rasha Sabah Haseeb a, Carl Henrik Görbitz b, Pål Rongved a,*
PMCID: PMC4350737  PMID: 25844186

In research towards new antagonists against the Liver X receptor, the important inter­mediate Fernholz acid Weinreb amide has been synthesized and characterized.

Keywords: crystal structure, Liver X receptor, obesity, steroid

Abstract

The literature compound 3β-hy­droxy-bis­nor-5-cholenic aldehyde is an important inter­mediate for the synthesis of new modulators of the nuclear oxysterol receptor Liver X. As part of our ongoing search for new LXR antagonists, the title compound, C24H39NO3, has proven to be an important inter­mediate in our new synthetic pathway, giving the corresponding aldehyde in high yield and in only three steps from the commercially available 3β-hy­droxy-bis­nor-5-cholenic acid. The title amide crystallized with two mol­ecules in the asymmetric unit, linked into helices by O—H⋯O hydrogen bonds involving the hy­droxy and carbonyl groups.

Chemical context  

In the nuclear receptor (NR) family, the two isoforms of the nuclear oxysterol receptor Liver X (LXRα and LXRβ) are emerging new drug targets. They are key players for a number of important processes related to disease, such as metabolic and cardiovascular diseases, lipid metabolism, inflammation and cancer (Steffensen & Gustafsson, 2006 ▸; Laffitte et al., 2003 ▸). LXR modulators have been investigated as potential drugs in the therapy of cardiovascular diseases, metabolic syndrome, regulation of inflammatory response and immunity, skin diseases and are effective in the treatment of murine models of atherosclerosis, diabetes and Alzheimer’s disease (Viennois et al., 2011 ▸, 2012 ▸; Jakobsson et al., 2012 ▸). Further, such agents have been shown to affect anti-inflammatory activity (Zhu & Bakovic, 2008 ▸; Zhu et al., 2012 ▸; Solan et al., 2011 ▸) and cell proliferation in a number of major cancer forms such as LNCaP human prostate cancer cells. (Viennois et al., 2012 ▸; Jakobsson et al., 2012 ▸). The ligand-binding pocket (LBP) of LXR allows binding of side-chain-oxygenated sterols (OHCs).

Recently, OHCs with a specific stereochemistry at the 23-hy­droxy­ated side-chain carbon have also been shown to regulate the Hedgehog signalling pathway (Hh), a key developmental pathway playing multiple roles in embryonic development, including stem-cell differentiation (Corman et al., 2012 ▸). In our drug-design programme, our retrosynthetic analysis for the establishment of synthetic routes to the pharmacophores in different OHCs revealed that the aldehyde analogue of the title compound [Fernholz aldehyde, (II)] is a key compound leading to a number of new library candidates for biological testing (Åstrand et al., 2014a ▸,b ▸). We have now identified the title compound, Fernholz Weinreb amide (I), as a new key inter­mediate to the Fernholz aldehyde, reducing the number of steps in the stereoselective synthesis. The O-TBDMS-protected Weinreb amide (I) may be used to prepare (II) using DIBALH, transferred to ketones with Grignard reagents or used for other synthetic transformations (Sivaraman et al., 2009 ▸; Davies et al., 2013 ▸). graphic file with name e-71-00275-scheme1.jpg

Structural commentary  

The asymmetric unit of (I), with two independent mol­ecules A and B, is depicted in Fig. 1 ▸ a. The macrocyclic part of (I) is also found in the naturally occurring hormone cholesterol and in close to 250 other steroids in the Cambridge Structural Database (CSD; Version 5.35 of November 2013; Groom & Allen, 2014 ▸). The mol­ecular conformation of this part of the mol­ecule is rigid, as shown from the overlay between A and B in Fig. 1 ▸ b. If the substituent at C17 is not included, the fit improves from 0.300 to 0.173 Å. Compound (I) also shares the hy­droxy group at C3 with cholesterol, but the N-meth­oxy-N-methyl­propanamide functionality has not previously been introduced into steroids; only the structure of the parent carb­oxy­lic acid has been reported previously (CSD refcode HAHSAL; Kurek-Tyrlik et al., 2004 ▸).

Figure 1.

Figure 1

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(a) The asymmetric unit of (I), showing the two mol­ecules A (light grey C atoms and atomic labels included) and B (dark C atoms). (b) An overlay between mol­ecules A (blue) and B (red), with an r.m.s. value of 0.300 Å. H atoms have been omitted in (b).

Supra­molecular features  

The unit-cell and the mol­ecular packing of (I) are shown in Fig. 2 ▸. As a class, steroids display a pronounced tendency to form crystal structures with more than one mol­ecule in the asymmetric unit; e.g. for about 35% of the 250 compounds mentioned above. The maximum Z′ value of 16 is reached for the high-temperature polymorph of cholesterol itself (CHOEST21: Hsu et al., 2002 ▸). Compound (I) has a Z′ value of 2, the two mol­ecules differing in the way the hy­droxy groups make inter­molecular hydrogen bonds (Table 1 ▸). Only the carbonyl group of mol­ecule A is an acceptor, while the hy­droxy groups of the B mol­ecules are both donors and acceptors and thus serve to link adjacent A mol­ecules along the a axis. In this process, stacks of either A or B mol­ecules along the a axis expose all the methyl groups on the outside, giving distinct regions with meth­yl–methyl inter­actions (Fig. 2 ▸ a). This is not a common mol­ecular aggregation pattern for steroids, but some related Z′ = 2 structures were found in the CSD, all hydrates without additional hydrogen-bond donors or acceptors in their C17 substituents (KESNAX: Sheng-Zhi et al., 1990 ▸; ZZZNVG01: Jiang et al., 2001 ▸; XOSLOH: Subash-Babu et al., 2009 ▸).

Figure 2.

Figure 2

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(a) Unit-cell and crystal packing viewed along the a axis. The colour coding is as in Fig. 1 ▸. The orange circles highlight a series of methyl groups; the blue area shades a hydrogen-bonded chain in shape of a flat helix. The chain, as a pink shape, is shown in more detail in (b) (the view is along the b axis).

Table 1. Hydrogen-bond geometry (, ).

DHA DH HA D A DHA
O3AH3AO3B i 0.86(4) 1.93(4) 2.782(4) 180(5)
O3BH3BO1A ii 0.83(4) 1.95(4) 2.768(3) 169(4)
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Symmetry codes: (i) Inline graphic; (ii) Inline graphic.

Synthesis and crystallization  

Compound (I) (348 mg) was dissolved in a minimum amount of boiling EtOAc (40 ml). The flask containing the solution was wrapped in aluminium foil and left overnight at room temperature to afford colourless crystalline needles.

Refinement  

Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. Coordinates were refined for hydroxyic H atoms; other H atoms were positioned with idealized geometry with fixed C—H = 0.95 (aromatic), 0.98 (meth­yl), 0.99 (methyl­ene) or 1.00 Å (methine) Å. U iso values were set to 1.2U eq of the carrier atom, or 1.5U eq for methyl and hy­droxy groups.

Table 2. Experimental details.

Crystal data
Chemical formula C24H39NO3
M r 389.56
Crystal system, space group Orthorhombic, P212121
Temperature (K) 105
a, b, c () 7.7256(4), 19.0030(9), 29.8162(15)
V (3) 4377.3(4)
Z 8
Radiation type Mo K
(mm1) 0.08
Crystal size (mm) 0.65 0.21 0.10
 
Data collection
Diffractometer Bruker D8 Vantage single-crystal CCD
Absorption correction Multi-scan (SADABS; Bruker, 2013 ▸)
T min, T max 0.852, 1.000
No. of measured, independent and observed [I > 2(I)] reflections 44800, 7739, 5760
R int 0.089
(sin /)max (1) 0.596
 
Refinement
R[F 2 > 2(F 2)], wR(F 2), S 0.048, 0.098, 1.04
No. of reflections 7739
No. of parameters 511
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
max, min (e 3) 0.21, 0.19
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Computer programs: APEX2 and SAINT-Plus (Bruker, 2013 ▸), SHELXS2013 (Sheldrick, 2008 ▸), SHELXL2013 (Sheldrick, 2015 ▸) and Mercury (Macrae et al., 2008 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989015001747/hb7343sup1.cif

e-71-00275-sup1.cif (1.3MB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015001747/hb7343Isup2.hkl

e-71-00275-Isup2.hkl (424KB, hkl)
Click here for additional data file. (9.7KB, cml)

Supporting information file. DOI: 10.1107/S2056989015001747/hb7343Isup3.cml

CCDC reference: 1045692

Additional supporting information: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Crystal data

C24H39NO3 Dx = 1.182 Mg m−3
Mr = 389.56 Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121 Cell parameters from 9981 reflections
a = 7.7256 (4) Å θ = 2.3–24.9°
b = 19.0030 (9) Å µ = 0.08 mm−1
c = 29.8162 (15) Å T = 105 K
V = 4377.3 (4) Å3 Flat needle, colourless
Z = 8 0.65 × 0.21 × 0.10 mm
F(000) = 1712
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Data collection

Bruker D8 Vantage single-crystal CCD diffractometer 7739 independent reflections
Radiation source: fine-focus sealed tube 5760 reflections with I > 2σ(I)
Graphite monochromator Rint = 0.089
Detector resolution: 8.3 pixels mm-1 θmax = 25.1°, θmin = 2.3°
Sets of exposures each taken over 0.5° ω rotation scans h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2013) k = −22→22
Tmin = 0.852, Tmax = 1.000 l = −35→35
44800 measured reflections
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Refinement

Refinement on F2 0 restraints
Least-squares matrix: full Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048 H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.098 w = 1/[σ2(Fo2) + (0.0448P)2 + 0.1501P] where P = (Fo2 + 2Fc2)/3
S = 1.04 (Δ/σ)max < 0.001
7739 reflections Δρmax = 0.21 e Å−3
511 parameters Δρmin = −0.19 e Å−3
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Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. No constraints or restraints applied
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
O1A 0.8266 (3) 0.67664 (11) 0.71479 (7) 0.0314 (6)
O2A 0.7377 (3) 0.50014 (11) 0.73658 (6) 0.0268 (6)
O3A 0.7896 (3) 0.69062 (13) 0.28850 (7) 0.0321 (6)
H3A 0.893 (6) 0.697 (2) 0.2790 (13) 0.048*
N1A 0.8127 (4) 0.56722 (14) 0.74205 (8) 0.0262 (7)
C1A 0.6249 (5) 0.67785 (17) 0.40586 (10) 0.0234 (8)
H1A 0.5099 0.6633 0.4171 0.028*
H2A 0.6438 0.7272 0.4153 0.028*
C2A 0.6223 (5) 0.67502 (18) 0.35440 (10) 0.0254 (8)
H4A 0.5928 0.6268 0.3444 0.030*
H5A 0.5327 0.7075 0.3428 0.030*
C3A 0.7964 (5) 0.69551 (17) 0.33605 (10) 0.0250 (8)
H31A 0.8210 0.7454 0.3446 0.030*
C4A 0.9375 (5) 0.64851 (17) 0.35544 (10) 0.0256 (8)
H41A 0.9215 0.6001 0.3440 0.031*
H42A 1.0515 0.6655 0.3449 0.031*
C5A 0.9374 (5) 0.64668 (16) 0.40622 (10) 0.0202 (8)
C6A 1.0815 (5) 0.65764 (16) 0.42912 (11) 0.0243 (8)
H61A 1.1832 0.6685 0.4126 0.029*
C7A 1.0964 (4) 0.65414 (17) 0.47918 (10) 0.0233 (8)
H71A 1.1122 0.7023 0.4911 0.028*
H72A 1.2005 0.6264 0.4872 0.028*
C8A 0.9385 (4) 0.62097 (16) 0.50128 (10) 0.0172 (7)
H81A 0.9438 0.5689 0.4968 0.021*
C9A 0.7721 (4) 0.64902 (16) 0.47901 (10) 0.0195 (7)
H91A 0.7785 0.7015 0.4811 0.023*
C10A 0.7637 (4) 0.63144 (15) 0.42821 (10) 0.0190 (7)
C11A 0.6082 (4) 0.62733 (18) 0.50481 (10) 0.0242 (8)
H11A 0.5089 0.6543 0.4928 0.029*
H11C 0.5855 0.5769 0.4990 0.029*
C12A 0.6168 (4) 0.63881 (17) 0.55576 (10) 0.0230 (8)
H12A 0.6176 0.6899 0.5621 0.028*
H12C 0.5122 0.6184 0.5699 0.028*
C13A 0.7778 (4) 0.60512 (15) 0.57639 (10) 0.0183 (7)
C14A 0.9350 (4) 0.63605 (16) 0.55146 (10) 0.0181 (8)
H14A 0.9255 0.6883 0.5545 0.022*
C15A 1.0903 (4) 0.61434 (16) 0.57969 (10) 0.0224 (8)
H15A 1.1881 0.6473 0.5754 0.027*
H15C 1.1289 0.5662 0.5719 0.027*
C16A 1.0214 (4) 0.61751 (17) 0.62834 (11) 0.0229 (8)
H16A 1.0735 0.6578 0.6445 0.027*
H16C 1.0508 0.5737 0.6446 0.027*
C17A 0.8214 (4) 0.62640 (16) 0.62533 (10) 0.0202 (8)
H17A 0.7948 0.6776 0.6287 0.024*
C18A 0.7693 (5) 0.52436 (15) 0.57226 (10) 0.0219 (8)
H18A 0.7630 0.5112 0.5405 0.033*
H18C 0.6664 0.5069 0.5879 0.033*
H18D 0.8732 0.5036 0.5857 0.033*
C19A 0.7198 (5) 0.55331 (16) 0.42009 (10) 0.0277 (9)
H19A 0.7365 0.5420 0.3883 0.042*
H19C 0.5991 0.5445 0.4284 0.042*
H19D 0.7961 0.5237 0.4384 0.042*
C20A 0.7291 (4) 0.58734 (16) 0.66317 (10) 0.0223 (8)
H20A 0.7572 0.5361 0.6608 0.027*
C21A 0.5318 (4) 0.59589 (18) 0.66345 (11) 0.0285 (9)
H21A 0.4833 0.5750 0.6362 0.043*
H21C 0.5025 0.6460 0.6645 0.043*
H21D 0.4836 0.5721 0.6898 0.043*
C22A 0.7925 (4) 0.61417 (17) 0.70820 (10) 0.0234 (8)
C23A 0.8338 (5) 0.58740 (19) 0.78883 (11) 0.0340 (9)
H23A 0.9119 0.5541 0.8037 0.051*
H23C 0.7209 0.5868 0.8038 0.051*
H23D 0.8829 0.6349 0.7905 0.051*
C24A 0.8716 (5) 0.44840 (17) 0.73243 (12) 0.0329 (9)
H24A 0.8205 0.4012 0.7337 0.049*
H24C 0.9545 0.4540 0.7570 0.049*
H24D 0.9314 0.4546 0.7037 0.049*
O1B 0.3248 (3) 0.29218 (11) 0.34061 (7) 0.0241 (6)
O2B 0.1000 (3) 0.43877 (11) 0.30237 (7) 0.0244 (6)
O3B 0.3740 (3) 0.28938 (12) 0.75771 (7) 0.0275 (6)
H3B 0.308 (5) 0.2590 (19) 0.7683 (11) 0.041*
N1B 0.2268 (4) 0.38484 (12) 0.30187 (8) 0.0212 (6)
C1B 0.1604 (4) 0.30886 (16) 0.64465 (9) 0.0203 (8)
H1B 0.0411 0.3224 0.6362 0.024*
H2B 0.1808 0.2606 0.6333 0.024*
C2B 0.1737 (4) 0.30804 (17) 0.69563 (10) 0.0222 (8)
H4B 0.1448 0.3552 0.7076 0.027*
H5B 0.0897 0.2739 0.7080 0.027*
C3B 0.3537 (4) 0.28808 (16) 0.70983 (10) 0.0204 (8)
H31B 0.3798 0.2396 0.6987 0.024*
C4B 0.4852 (4) 0.33881 (16) 0.69055 (10) 0.0216 (8)
H41B 0.6031 0.3220 0.6980 0.026*
H42B 0.4695 0.3855 0.7047 0.026*
C5B 0.4690 (4) 0.34639 (16) 0.63992 (10) 0.0167 (8)
C6B 0.6090 (4) 0.34157 (15) 0.61433 (10) 0.0190 (8)
H61B 0.7165 0.3331 0.6288 0.023*
C7B 0.6103 (4) 0.34850 (16) 0.56420 (10) 0.0181 (7)
H71B 0.6346 0.3018 0.5508 0.022*
H72B 0.7053 0.3806 0.5554 0.022*
C8B 0.4407 (4) 0.37637 (15) 0.54505 (10) 0.0148 (7)
H81B 0.4377 0.4287 0.5487 0.018*
C9B 0.2861 (4) 0.34433 (15) 0.56994 (9) 0.0148 (7)
H91B 0.2973 0.2922 0.5666 0.018*
C10B 0.2883 (4) 0.35925 (15) 0.62135 (9) 0.0164 (7)
C11B 0.1142 (4) 0.36437 (16) 0.54751 (9) 0.0186 (8)
H11B 0.0926 0.4151 0.5525 0.022*
H11E 0.0194 0.3379 0.5622 0.022*
C12B 0.1090 (4) 0.34958 (17) 0.49675 (10) 0.0195 (8)
H12B 0.1125 0.2981 0.4917 0.023*
H12E −0.0013 0.3675 0.4843 0.023*
C13B 0.2603 (4) 0.38405 (15) 0.47190 (10) 0.0159 (7)
C14B 0.4271 (4) 0.35862 (16) 0.49529 (10) 0.0159 (7)
H14B 0.4238 0.3061 0.4937 0.019*
C15B 0.5736 (4) 0.38110 (16) 0.46425 (10) 0.0185 (8)
H15B 0.6739 0.3489 0.4670 0.022*
H15E 0.6119 0.4296 0.4711 0.022*
C16B 0.4928 (4) 0.37679 (17) 0.41675 (10) 0.0190 (8)
H16B 0.5038 0.4225 0.4011 0.023*
H16E 0.5516 0.3402 0.3987 0.023*
C17B 0.2998 (4) 0.35775 (15) 0.42354 (9) 0.0163 (7)
H17B 0.2924 0.3052 0.4242 0.020*
C18B 0.2422 (5) 0.46448 (14) 0.47231 (10) 0.0205 (8)
H18B 0.2399 0.4813 0.5034 0.031*
H18E 0.1344 0.4779 0.4572 0.031*
H18F 0.3407 0.4856 0.4566 0.031*
C19B 0.2362 (5) 0.43602 (15) 0.63154 (10) 0.0238 (8)
H19B 0.1118 0.4420 0.6264 0.036*
H19E 0.3007 0.4679 0.6118 0.036*
H19F 0.2632 0.4470 0.6629 0.036*
C20B 0.1861 (4) 0.38264 (15) 0.38456 (10) 0.0171 (7)
H20B 0.1963 0.4349 0.3819 0.021*
C21B −0.0056 (4) 0.36319 (18) 0.38993 (10) 0.0241 (8)
H21B −0.0159 0.3127 0.3961 0.036*
H21E −0.0680 0.3745 0.3622 0.036*
H21F −0.0554 0.3899 0.4149 0.036*
C22B 0.2502 (4) 0.34904 (16) 0.34128 (10) 0.0180 (7)
C23B 0.2346 (5) 0.34870 (17) 0.25866 (10) 0.0297 (9)
H23B 0.3161 0.3093 0.2606 0.045*
H23E 0.2735 0.3817 0.2355 0.045*
H23F 0.1194 0.3309 0.2509 0.045*
C24B 0.1771 (5) 0.50416 (17) 0.28946 (11) 0.0323 (9)
H24B 0.2626 0.5182 0.3120 0.048*
H24E 0.0872 0.5404 0.2872 0.048*
H24F 0.2342 0.4987 0.2603 0.048*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
O1A 0.0366 (16) 0.0248 (14) 0.0329 (14) 0.0014 (12) −0.0019 (12) −0.0128 (10)
O2A 0.0243 (14) 0.0266 (13) 0.0295 (13) −0.0025 (12) 0.0005 (11) −0.0031 (10)
O3A 0.0298 (16) 0.0442 (15) 0.0224 (14) −0.0058 (13) 0.0051 (12) 0.0016 (11)
N1A 0.0296 (19) 0.0282 (16) 0.0207 (16) −0.0023 (14) 0.0012 (14) −0.0059 (13)
C1A 0.018 (2) 0.027 (2) 0.025 (2) 0.0001 (16) 0.0036 (16) 0.0005 (14)
C2A 0.021 (2) 0.028 (2) 0.027 (2) −0.0012 (17) 0.0015 (16) 0.0008 (15)
C3A 0.030 (2) 0.0219 (18) 0.0228 (19) −0.0021 (16) 0.0047 (17) −0.0006 (14)
C4A 0.024 (2) 0.0242 (19) 0.028 (2) −0.0035 (17) 0.0075 (16) −0.0017 (15)
C5A 0.020 (2) 0.0133 (17) 0.028 (2) 0.0011 (16) 0.0059 (17) −0.0014 (14)
C6A 0.016 (2) 0.0227 (19) 0.034 (2) 0.0007 (16) 0.0084 (18) 0.0027 (15)
C7A 0.0145 (19) 0.0252 (18) 0.030 (2) −0.0010 (16) 0.0016 (16) 0.0002 (15)
C8A 0.0149 (18) 0.0132 (16) 0.0235 (19) 0.0002 (15) 0.0008 (15) −0.0028 (13)
C9A 0.0172 (19) 0.0161 (16) 0.0253 (18) 0.0005 (15) 0.0024 (16) −0.0020 (14)
C10A 0.0140 (18) 0.0156 (16) 0.0274 (18) −0.0007 (15) 0.0015 (16) −0.0008 (13)
C11A 0.016 (2) 0.033 (2) 0.024 (2) −0.0011 (17) −0.0005 (16) 0.0009 (15)
C12A 0.015 (2) 0.0266 (19) 0.027 (2) 0.0000 (16) 0.0030 (16) −0.0003 (15)
C13A 0.0190 (19) 0.0149 (16) 0.0210 (18) 0.0003 (15) 0.0005 (16) −0.0040 (13)
C14A 0.0151 (19) 0.0112 (17) 0.0279 (19) −0.0008 (15) 0.0012 (16) −0.0009 (14)
C15A 0.019 (2) 0.0187 (18) 0.030 (2) 0.0024 (16) 0.0004 (16) 0.0000 (14)
C16A 0.021 (2) 0.0176 (18) 0.030 (2) 0.0004 (15) −0.0036 (16) −0.0021 (14)
C17A 0.022 (2) 0.0126 (16) 0.0259 (19) 0.0026 (15) −0.0009 (16) −0.0042 (13)
C18A 0.024 (2) 0.0205 (17) 0.0214 (18) −0.0060 (16) 0.0004 (16) −0.0035 (13)
C19A 0.033 (2) 0.0234 (18) 0.0266 (19) −0.0068 (17) 0.0025 (18) −0.0024 (14)
C20A 0.023 (2) 0.0185 (17) 0.0254 (19) 0.0032 (16) 0.0014 (17) −0.0062 (14)
C21A 0.026 (2) 0.031 (2) 0.028 (2) −0.0026 (17) 0.0015 (17) −0.0005 (16)
C22A 0.018 (2) 0.026 (2) 0.026 (2) 0.0031 (16) 0.0052 (16) −0.0074 (15)
C23A 0.028 (2) 0.050 (2) 0.024 (2) 0.0018 (19) 0.0016 (18) −0.0092 (17)
C24A 0.029 (2) 0.028 (2) 0.042 (2) 0.0008 (18) 0.0009 (18) 0.0000 (16)
O1B 0.0315 (15) 0.0202 (12) 0.0206 (12) 0.0058 (11) −0.0002 (11) −0.0011 (9)
O2B 0.0215 (14) 0.0249 (12) 0.0269 (13) 0.0064 (11) 0.0017 (11) 0.0063 (10)
O3B 0.0290 (16) 0.0349 (15) 0.0184 (14) −0.0094 (12) −0.0034 (11) 0.0058 (10)
N1B 0.0221 (17) 0.0238 (14) 0.0177 (15) 0.0091 (14) 0.0002 (13) 0.0021 (11)
C1B 0.0157 (19) 0.0251 (18) 0.0199 (18) 0.0001 (16) −0.0014 (15) 0.0018 (14)
C2B 0.021 (2) 0.0228 (18) 0.0226 (19) −0.0033 (15) 0.0003 (16) 0.0018 (14)
C3B 0.026 (2) 0.0195 (17) 0.0153 (18) −0.0002 (16) −0.0022 (15) 0.0001 (14)
C4B 0.021 (2) 0.0216 (19) 0.0224 (19) −0.0043 (15) −0.0039 (16) −0.0014 (14)
C5B 0.019 (2) 0.0121 (17) 0.0191 (18) −0.0028 (15) −0.0009 (15) 0.0001 (13)
C6B 0.016 (2) 0.0168 (17) 0.025 (2) −0.0021 (15) −0.0064 (16) 0.0027 (14)
C7B 0.0160 (19) 0.0149 (16) 0.0233 (19) 0.0013 (15) −0.0013 (15) −0.0015 (13)
C8B 0.0138 (18) 0.0111 (16) 0.0196 (18) 0.0002 (15) −0.0015 (14) −0.0002 (13)
C9B 0.0146 (19) 0.0116 (15) 0.0183 (17) 0.0006 (14) −0.0006 (14) −0.0002 (12)
C10B 0.0142 (19) 0.0160 (16) 0.0189 (17) −0.0010 (14) −0.0013 (15) −0.0006 (13)
C11B 0.0130 (19) 0.0255 (19) 0.0173 (18) −0.0004 (15) 0.0012 (15) −0.0004 (14)
C12B 0.0125 (19) 0.0246 (18) 0.0213 (19) −0.0004 (16) −0.0011 (15) −0.0006 (14)
C13B 0.0136 (18) 0.0156 (16) 0.0184 (17) 0.0006 (15) −0.0038 (14) −0.0019 (13)
C14B 0.0148 (18) 0.0118 (16) 0.0210 (18) −0.0003 (15) −0.0011 (15) −0.0009 (13)
C15B 0.0156 (19) 0.0181 (17) 0.0217 (19) −0.0012 (16) 0.0017 (15) 0.0015 (13)
C16B 0.0165 (19) 0.0193 (18) 0.0214 (18) −0.0002 (15) 0.0005 (15) −0.0013 (14)
C17B 0.0161 (19) 0.0133 (16) 0.0195 (17) 0.0013 (14) −0.0010 (15) 0.0005 (13)
C18B 0.022 (2) 0.0203 (17) 0.0193 (17) 0.0061 (17) −0.0020 (16) −0.0027 (13)
C19B 0.028 (2) 0.0229 (17) 0.0202 (18) 0.0055 (18) 0.0004 (16) −0.0013 (13)
C20B 0.0175 (19) 0.0151 (16) 0.0188 (18) −0.0015 (14) 0.0012 (15) 0.0011 (13)
C21B 0.019 (2) 0.033 (2) 0.0197 (18) 0.0022 (16) −0.0010 (15) 0.0005 (15)
C22B 0.0123 (18) 0.0189 (17) 0.0229 (18) −0.0049 (17) −0.0040 (15) −0.0017 (14)
C23B 0.034 (2) 0.036 (2) 0.0190 (18) 0.0055 (19) −0.0005 (17) −0.0012 (15)
C24B 0.038 (2) 0.0243 (19) 0.035 (2) 0.0023 (17) 0.0045 (18) 0.0064 (16)
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Geometric parameters (Å, º)

O1A—C22A 1.232 (4) O1B—C22B 1.225 (4)
O2A—N1A 1.410 (3) O2B—N1B 1.418 (3)
O2A—C24A 1.433 (4) O2B—C24B 1.431 (4)
O3A—C3A 1.422 (4) O3B—C3B 1.436 (4)
O3A—H3A 0.86 (4) O3B—H3B 0.83 (4)
N1A—C22A 1.356 (4) N1B—C22B 1.370 (4)
N1A—C23A 1.456 (4) N1B—C23B 1.461 (4)
C1A—C2A 1.535 (4) C1B—C2B 1.523 (4)
C1A—C10A 1.540 (4) C1B—C10B 1.541 (4)
C1A—H1A 0.9900 C1B—H1B 0.9900
C1A—H2A 0.9900 C1B—H2B 0.9900
C2A—C3A 1.503 (5) C2B—C3B 1.503 (4)
C2A—H4A 0.9900 C2B—H4B 0.9900
C2A—H5A 0.9900 C2B—H5B 0.9900
C3A—C4A 1.523 (5) C3B—C4B 1.513 (4)
C3A—H31A 1.0000 C3B—H31B 1.0000
C4A—C5A 1.514 (4) C4B—C5B 1.522 (4)
C4A—H41A 0.9900 C4B—H41B 0.9900
C4A—H42A 0.9900 C4B—H42B 0.9900
C5A—C6A 1.322 (5) C5B—C6B 1.327 (4)
C5A—C10A 1.521 (5) C5B—C10B 1.522 (4)
C6A—C7A 1.499 (4) C6B—C7B 1.501 (4)
C6A—H61A 0.9500 C6B—H61B 0.9500
C7A—C8A 1.523 (5) C7B—C8B 1.524 (4)
C7A—H71A 0.9900 C7B—H71B 0.9900
C7A—H72A 0.9900 C7B—H72B 0.9900
C8A—C14A 1.524 (4) C8B—C14B 1.525 (4)
C8A—C9A 1.542 (4) C8B—C9B 1.532 (4)
C8A—H81A 1.0000 C8B—H81B 1.0000
C9A—C11A 1.538 (4) C9B—C11B 1.535 (4)
C9A—C10A 1.552 (4) C9B—C10B 1.559 (4)
C9A—H91A 1.0000 C9B—H91B 1.0000
C10A—C19A 1.542 (4) C10B—C19B 1.544 (4)
C11A—C12A 1.536 (4) C11B—C12B 1.540 (4)
C11A—H11A 0.9900 C11B—H11B 0.9900
C11A—H11C 0.9900 C11B—H11E 0.9900
C12A—C13A 1.528 (4) C12B—C13B 1.531 (4)
C12A—H12A 0.9900 C12B—H12B 0.9900
C12A—H12C 0.9900 C12B—H12E 0.9900
C13A—C14A 1.541 (4) C13B—C18B 1.535 (4)
C13A—C18A 1.541 (4) C13B—C14B 1.543 (4)
C13A—C17A 1.551 (4) C13B—C17B 1.556 (4)
C14A—C15A 1.522 (4) C14B—C15B 1.523 (4)
C14A—H14A 1.0000 C14B—H14B 1.0000
C15A—C16A 1.546 (4) C15B—C16B 1.550 (4)
C15A—H15A 0.9900 C15B—H15B 0.9900
C15A—H15C 0.9900 C15B—H15E 0.9900
C16A—C17A 1.557 (5) C16B—C17B 1.548 (4)
C16A—H16A 0.9900 C16B—H16B 0.9900
C16A—H16C 0.9900 C16B—H16E 0.9900
C17A—C20A 1.527 (4) C17B—C20B 1.531 (4)
C17A—H17A 1.0000 C17B—H17B 1.0000
C18A—H18A 0.9800 C18B—H18B 0.9800
C18A—H18C 0.9800 C18B—H18E 0.9800
C18A—H18D 0.9800 C18B—H18F 0.9800
C19A—H19A 0.9800 C19B—H19B 0.9800
C19A—H19C 0.9800 C19B—H19E 0.9800
C19A—H19D 0.9800 C19B—H19F 0.9800
C20A—C22A 1.517 (4) C20B—C22B 1.523 (4)
C20A—C21A 1.533 (5) C20B—C21B 1.535 (4)
C20A—H20A 1.0000 C20B—H20B 1.0000
C21A—H21A 0.9800 C21B—H21B 0.9800
C21A—H21C 0.9800 C21B—H21E 0.9800
C21A—H21D 0.9800 C21B—H21F 0.9800
C23A—H23A 0.9800 C23B—H23B 0.9800
C23A—H23C 0.9800 C23B—H23E 0.9800
C23A—H23D 0.9800 C23B—H23F 0.9800
C24A—H24A 0.9800 C24B—H24B 0.9800
C24A—H24C 0.9800 C24B—H24E 0.9800
C24A—H24D 0.9800 C24B—H24F 0.9800
N1A—O2A—C24A 109.5 (2) N1B—O2B—C24B 109.7 (2)
C3A—O3A—H3A 107 (3) C3B—O3B—H3B 107 (2)
C22A—N1A—O2A 117.5 (2) C22B—N1B—O2B 116.2 (2)
C22A—N1A—C23A 123.6 (3) C22B—N1B—C23B 121.2 (2)
O2A—N1A—C23A 113.3 (2) O2B—N1B—C23B 112.2 (2)
C2A—C1A—C10A 114.9 (3) C2B—C1B—C10B 114.4 (3)
C2A—C1A—H1A 108.5 C2B—C1B—H1B 108.7
C10A—C1A—H1A 108.5 C10B—C1B—H1B 108.7
C2A—C1A—H2A 108.5 C2B—C1B—H2B 108.7
C10A—C1A—H2A 108.5 C10B—C1B—H2B 108.7
H1A—C1A—H2A 107.5 H1B—C1B—H2B 107.6
C3A—C2A—C1A 110.0 (3) C3B—C2B—C1B 110.3 (3)
C3A—C2A—H4A 109.7 C3B—C2B—H4B 109.6
C1A—C2A—H4A 109.7 C1B—C2B—H4B 109.6
C3A—C2A—H5A 109.7 C3B—C2B—H5B 109.6
C1A—C2A—H5A 109.7 C1B—C2B—H5B 109.6
H4A—C2A—H5A 108.2 H4B—C2B—H5B 108.1
O3A—C3A—C2A 108.2 (3) O3B—C3B—C2B 112.1 (3)
O3A—C3A—C4A 111.5 (3) O3B—C3B—C4B 107.1 (2)
C2A—C3A—C4A 110.5 (3) C2B—C3B—C4B 110.7 (2)
O3A—C3A—H31A 108.9 O3B—C3B—H31B 109.0
C2A—C3A—H31A 108.9 C2B—C3B—H31B 109.0
C4A—C3A—H31A 108.9 C4B—C3B—H31B 109.0
C5A—C4A—C3A 113.1 (3) C3B—C4B—C5B 112.5 (3)
C5A—C4A—H41A 109.0 C3B—C4B—H41B 109.1
C3A—C4A—H41A 109.0 C5B—C4B—H41B 109.1
C5A—C4A—H42A 109.0 C3B—C4B—H42B 109.1
C3A—C4A—H42A 109.0 C5B—C4B—H42B 109.1
H41A—C4A—H42A 107.8 H41B—C4B—H42B 107.8
C6A—C5A—C4A 120.8 (3) C6B—C5B—C4B 119.8 (3)
C6A—C5A—C10A 123.3 (3) C6B—C5B—C10B 123.4 (3)
C4A—C5A—C10A 115.8 (3) C4B—C5B—C10B 116.8 (3)
C5A—C6A—C7A 124.9 (3) C5B—C6B—C7B 124.9 (3)
C5A—C6A—H61A 117.5 C5B—C6B—H61B 117.6
C7A—C6A—H61A 117.5 C7B—C6B—H61B 117.6
C6A—C7A—C8A 112.8 (3) C6B—C7B—C8B 113.5 (3)
C6A—C7A—H71A 109.0 C6B—C7B—H71B 108.9
C8A—C7A—H71A 109.0 C8B—C7B—H71B 108.9
C6A—C7A—H72A 109.0 C6B—C7B—H72B 108.9
C8A—C7A—H72A 109.0 C8B—C7B—H72B 108.9
H71A—C7A—H72A 107.8 H71B—C7B—H72B 107.7
C7A—C8A—C14A 111.2 (3) C7B—C8B—C14B 110.3 (3)
C7A—C8A—C9A 109.8 (2) C7B—C8B—C9B 110.5 (2)
C14A—C8A—C9A 110.1 (3) C14B—C8B—C9B 109.3 (2)
C7A—C8A—H81A 108.6 C7B—C8B—H81B 108.9
C14A—C8A—H81A 108.6 C14B—C8B—H81B 108.9
C9A—C8A—H81A 108.6 C9B—C8B—H81B 108.9
C11A—C9A—C8A 112.2 (2) C8B—C9B—C11B 111.4 (2)
C11A—C9A—C10A 113.3 (3) C8B—C9B—C10B 113.3 (2)
C8A—C9A—C10A 112.4 (2) C11B—C9B—C10B 113.1 (2)
C11A—C9A—H91A 106.1 C8B—C9B—H91B 106.1
C8A—C9A—H91A 106.1 C11B—C9B—H91B 106.1
C10A—C9A—H91A 106.1 C10B—C9B—H91B 106.1
C5A—C10A—C1A 108.6 (2) C5B—C10B—C1B 108.9 (2)
C5A—C10A—C19A 108.0 (3) C5B—C10B—C19B 108.6 (3)
C1A—C10A—C19A 109.3 (3) C1B—C10B—C19B 109.4 (3)
C5A—C10A—C9A 110.1 (3) C5B—C10B—C9B 109.8 (3)
C1A—C10A—C9A 109.1 (2) C1B—C10B—C9B 108.9 (2)
C19A—C10A—C9A 111.7 (2) C19B—C10B—C9B 111.3 (2)
C12A—C11A—C9A 114.9 (3) C9B—C11B—C12B 113.9 (3)
C12A—C11A—H11A 108.5 C9B—C11B—H11B 108.8
C9A—C11A—H11A 108.5 C12B—C11B—H11B 108.8
C12A—C11A—H11C 108.5 C9B—C11B—H11E 108.8
C9A—C11A—H11C 108.5 C12B—C11B—H11E 108.8
H11A—C11A—H11C 107.5 H11B—C11B—H11E 107.7
C13A—C12A—C11A 112.0 (3) C13B—C12B—C11B 112.2 (3)
C13A—C12A—H12A 109.2 C13B—C12B—H12B 109.2
C11A—C12A—H12A 109.2 C11B—C12B—H12B 109.2
C13A—C12A—H12C 109.2 C13B—C12B—H12E 109.2
C11A—C12A—H12C 109.2 C11B—C12B—H12E 109.2
H12A—C12A—H12C 107.9 H12B—C12B—H12E 107.9
C12A—C13A—C14A 106.7 (2) C12B—C13B—C18B 110.6 (3)
C12A—C13A—C18A 110.5 (3) C12B—C13B—C14B 106.6 (2)
C14A—C13A—C18A 112.0 (3) C18B—C13B—C14B 112.6 (3)
C12A—C13A—C17A 116.5 (3) C12B—C13B—C17B 117.4 (2)
C14A—C13A—C17A 100.5 (3) C18B—C13B—C17B 110.2 (2)
C18A—C13A—C17A 110.1 (2) C14B—C13B—C17B 98.9 (2)
C15A—C14A—C8A 118.6 (3) C15B—C14B—C8B 118.5 (3)
C15A—C14A—C13A 104.6 (2) C15B—C14B—C13B 105.0 (2)
C8A—C14A—C13A 114.6 (3) C8B—C14B—C13B 115.3 (3)
C15A—C14A—H14A 106.1 C15B—C14B—H14B 105.6
C8A—C14A—H14A 106.1 C8B—C14B—H14B 105.6
C13A—C14A—H14A 106.1 C13B—C14B—H14B 105.6
C14A—C15A—C16A 103.7 (3) C14B—C15B—C16B 103.9 (3)
C14A—C15A—H15A 111.0 C14B—C15B—H15B 111.0
C16A—C15A—H15A 111.0 C16B—C15B—H15B 111.0
C14A—C15A—H15C 111.0 C14B—C15B—H15E 111.0
C16A—C15A—H15C 111.0 C16B—C15B—H15E 111.0
H15A—C15A—H15C 109.0 H15B—C15B—H15E 109.0
C15A—C16A—C17A 107.0 (3) C17B—C16B—C15B 106.3 (2)
C15A—C16A—H16A 110.3 C17B—C16B—H16B 110.5
C17A—C16A—H16A 110.3 C15B—C16B—H16B 110.5
C15A—C16A—H16C 110.3 C17B—C16B—H16E 110.5
C17A—C16A—H16C 110.3 C15B—C16B—H16E 110.5
H16A—C16A—H16C 108.6 H16B—C16B—H16E 108.7
C20A—C17A—C13A 117.8 (3) C20B—C17B—C16B 112.4 (2)
C20A—C17A—C16A 111.6 (3) C20B—C17B—C13B 119.5 (2)
C13A—C17A—C16A 104.0 (3) C16B—C17B—C13B 103.6 (2)
C20A—C17A—H17A 107.7 C20B—C17B—H17B 106.9
C13A—C17A—H17A 107.7 C16B—C17B—H17B 106.9
C16A—C17A—H17A 107.7 C13B—C17B—H17B 106.9
C13A—C18A—H18A 109.5 C13B—C18B—H18B 109.5
C13A—C18A—H18C 109.5 C13B—C18B—H18E 109.5
H18A—C18A—H18C 109.5 H18B—C18B—H18E 109.5
C13A—C18A—H18D 109.5 C13B—C18B—H18F 109.5
H18A—C18A—H18D 109.5 H18B—C18B—H18F 109.5
H18C—C18A—H18D 109.5 H18E—C18B—H18F 109.5
C10A—C19A—H19A 109.5 C10B—C19B—H19B 109.5
C10A—C19A—H19C 109.5 C10B—C19B—H19E 109.5
H19A—C19A—H19C 109.5 H19B—C19B—H19E 109.5
C10A—C19A—H19D 109.5 C10B—C19B—H19F 109.5
H19A—C19A—H19D 109.5 H19B—C19B—H19F 109.5
H19C—C19A—H19D 109.5 H19E—C19B—H19F 109.5
C22A—C20A—C17A 109.9 (3) C22B—C20B—C17B 109.1 (3)
C22A—C20A—C21A 106.3 (3) C22B—C20B—C21B 107.5 (3)
C17A—C20A—C21A 114.6 (3) C17B—C20B—C21B 113.6 (2)
C22A—C20A—H20A 108.6 C22B—C20B—H20B 108.8
C17A—C20A—H20A 108.6 C17B—C20B—H20B 108.8
C21A—C20A—H20A 108.6 C21B—C20B—H20B 108.8
C20A—C21A—H21A 109.5 C20B—C21B—H21B 109.5
C20A—C21A—H21C 109.5 C20B—C21B—H21E 109.5
H21A—C21A—H21C 109.5 H21B—C21B—H21E 109.5
C20A—C21A—H21D 109.5 C20B—C21B—H21F 109.5
H21A—C21A—H21D 109.5 H21B—C21B—H21F 109.5
H21C—C21A—H21D 109.5 H21E—C21B—H21F 109.5
O1A—C22A—N1A 119.4 (3) O1B—C22B—N1B 119.1 (3)
O1A—C22A—C20A 122.3 (3) O1B—C22B—C20B 122.5 (3)
N1A—C22A—C20A 118.3 (3) N1B—C22B—C20B 118.4 (3)
N1A—C23A—H23A 109.5 N1B—C23B—H23B 109.5
N1A—C23A—H23C 109.5 N1B—C23B—H23E 109.5
H23A—C23A—H23C 109.5 H23B—C23B—H23E 109.5
N1A—C23A—H23D 109.5 N1B—C23B—H23F 109.5
H23A—C23A—H23D 109.5 H23B—C23B—H23F 109.5
H23C—C23A—H23D 109.5 H23E—C23B—H23F 109.5
O2A—C24A—H24A 109.5 O2B—C24B—H24B 109.5
O2A—C24A—H24C 109.5 O2B—C24B—H24E 109.5
H24A—C24A—H24C 109.5 H24B—C24B—H24E 109.5
O2A—C24A—H24D 109.5 O2B—C24B—H24F 109.5
H24A—C24A—H24D 109.5 H24B—C24B—H24F 109.5
H24C—C24A—H24D 109.5 H24E—C24B—H24F 109.5
C24A—O2A—N1A—C22A 112.3 (3) C24B—O2B—N1B—C22B 122.9 (3)
C24A—O2A—N1A—C23A −93.4 (3) C24B—O2B—N1B—C23B −91.7 (3)
C10A—C1A—C2A—C3A −57.2 (4) C10B—C1B—C2B—C3B −58.0 (3)
C1A—C2A—C3A—O3A 178.6 (3) C1B—C2B—C3B—O3B 177.7 (2)
C1A—C2A—C3A—C4A 56.3 (4) C1B—C2B—C3B—C4B 58.2 (3)
O3A—C3A—C4A—C5A −174.3 (3) O3B—C3B—C4B—C5B −176.0 (3)
C2A—C3A—C4A—C5A −53.9 (4) C2B—C3B—C4B—C5B −53.5 (4)
C3A—C4A—C5A—C6A −129.7 (3) C3B—C4B—C5B—C6B −131.5 (3)
C3A—C4A—C5A—C10A 50.5 (4) C3B—C4B—C5B—C10B 48.4 (4)
C4A—C5A—C6A—C7A −177.5 (3) C4B—C5B—C6B—C7B −179.6 (3)
C10A—C5A—C6A—C7A 2.3 (5) C10B—C5B—C6B—C7B 0.5 (5)
C5A—C6A—C7A—C8A 12.6 (5) C5B—C6B—C7B—C8B 11.6 (4)
C6A—C7A—C8A—C14A −164.5 (3) C6B—C7B—C8B—C14B −160.5 (2)
C6A—C7A—C8A—C9A −42.5 (3) C6B—C7B—C8B—C9B −39.6 (3)
C7A—C8A—C9A—C11A −170.4 (3) C7B—C8B—C9B—C11B −172.9 (3)
C14A—C8A—C9A—C11A −47.7 (3) C14B—C8B—C9B—C11B −51.4 (3)
C7A—C8A—C9A—C10A 60.5 (3) C7B—C8B—C9B—C10B 58.2 (3)
C14A—C8A—C9A—C10A −176.8 (2) C14B—C8B—C9B—C10B 179.7 (2)
C6A—C5A—C10A—C1A 133.4 (3) C6B—C5B—C10B—C1B 135.2 (3)
C4A—C5A—C10A—C1A −46.8 (4) C4B—C5B—C10B—C1B −44.7 (3)
C6A—C5A—C10A—C19A −108.2 (3) C6B—C5B—C10B—C19B −105.8 (3)
C4A—C5A—C10A—C19A 71.6 (3) C4B—C5B—C10B—C19B 74.3 (3)
C6A—C5A—C10A—C9A 14.0 (4) C6B—C5B—C10B—C9B 16.1 (4)
C4A—C5A—C10A—C9A −166.2 (3) C4B—C5B—C10B—C9B −163.8 (2)
C2A—C1A—C10A—C5A 50.5 (4) C2B—C1B—C10B—C5B 49.4 (3)
C2A—C1A—C10A—C19A −67.1 (4) C2B—C1B—C10B—C19B −69.1 (3)
C2A—C1A—C10A—C9A 170.5 (3) C2B—C1B—C10B—C9B 169.1 (3)
C11A—C9A—C10A—C5A −173.5 (2) C8B—C9B—C10B—C5B −45.2 (3)
C8A—C9A—C10A—C5A −45.0 (3) C11B—C9B—C10B—C5B −173.2 (2)
C11A—C9A—C10A—C1A 67.4 (3) C8B—C9B—C10B—C1B −164.3 (2)
C8A—C9A—C10A—C1A −164.1 (3) C11B—C9B—C10B—C1B 67.7 (3)
C11A—C9A—C10A—C19A −53.5 (4) C8B—C9B—C10B—C19B 75.1 (3)
C8A—C9A—C10A—C19A 75.0 (3) C11B—C9B—C10B—C19B −52.9 (3)
C8A—C9A—C11A—C12A 47.0 (4) C8B—C9B—C11B—C12B 51.4 (3)
C10A—C9A—C11A—C12A 175.6 (3) C10B—C9B—C11B—C12B −179.6 (2)
C9A—C11A—C12A—C13A −52.4 (4) C9B—C11B—C12B—C13B −54.1 (3)
C11A—C12A—C13A—C14A 56.0 (3) C11B—C12B—C13B—C18B −68.3 (3)
C11A—C12A—C13A—C18A −66.0 (3) C11B—C12B—C13B—C14B 54.4 (3)
C11A—C12A—C13A—C17A 167.3 (3) C11B—C12B—C13B—C17B 164.0 (3)
C7A—C8A—C14A—C15A −56.5 (4) C7B—C8B—C14B—C15B −54.4 (4)
C9A—C8A—C14A—C15A −178.3 (3) C9B—C8B—C14B—C15B −176.1 (3)
C7A—C8A—C14A—C13A 179.2 (2) C7B—C8B—C14B—C13B 179.9 (2)
C9A—C8A—C14A—C13A 57.4 (3) C9B—C8B—C14B—C13B 58.3 (3)
C12A—C13A—C14A—C15A 167.5 (2) C12B—C13B—C14B—C15B 168.6 (2)
C18A—C13A—C14A—C15A −71.4 (3) C18B—C13B—C14B—C15B −69.9 (3)
C17A—C13A—C14A—C15A 45.5 (3) C17B—C13B—C14B—C15B 46.4 (3)
C12A—C13A—C14A—C8A −61.0 (3) C12B—C13B—C14B—C8B −59.0 (3)
C18A—C13A—C14A—C8A 60.1 (3) C18B—C13B—C14B—C8B 62.4 (3)
C17A—C13A—C14A—C8A 177.0 (2) C17B—C13B—C14B—C8B 178.8 (2)
C8A—C14A—C15A—C16A −164.3 (3) C8B—C14B—C15B—C16B −162.5 (3)
C13A—C14A—C15A—C16A −35.2 (3) C13B—C14B—C15B—C16B −32.0 (3)
C14A—C15A—C16A—C17A 11.0 (3) C14B—C15B—C16B—C17B 4.4 (3)
C12A—C13A—C17A—C20A 83.7 (3) C15B—C16B—C17B—C20B 154.5 (2)
C14A—C13A—C17A—C20A −161.5 (3) C15B—C16B—C17B—C13B 24.2 (3)
C18A—C13A—C17A—C20A −43.2 (4) C12B—C13B—C17B—C20B 77.7 (3)
C12A—C13A—C17A—C16A −152.3 (3) C18B—C13B—C17B—C20B −50.2 (4)
C14A—C13A—C17A—C16A −37.4 (3) C14B—C13B—C17B—C20B −168.3 (3)
C18A—C13A—C17A—C16A 80.9 (3) C12B—C13B—C17B—C16B −156.4 (3)
C15A—C16A—C17A—C20A 144.9 (2) C18B—C13B—C17B—C16B 75.7 (3)
C15A—C16A—C17A—C13A 16.9 (3) C14B—C13B—C17B—C16B −42.5 (3)
C13A—C17A—C20A—C22A 178.5 (3) C16B—C17B—C20B—C22B 58.9 (3)
C16A—C17A—C20A—C22A 58.3 (3) C13B—C17B—C20B—C22B −179.5 (3)
C13A—C17A—C20A—C21A −62.0 (4) C16B—C17B—C20B—C21B 178.9 (3)
C16A—C17A—C20A—C21A 177.9 (3) C13B—C17B—C20B—C21B −59.5 (4)
O2A—N1A—C22A—O1A 166.4 (3) O2B—N1B—C22B—O1B 162.6 (3)
C23A—N1A—C22A—O1A 14.9 (5) C23B—N1B—C22B—O1B 20.5 (5)
O2A—N1A—C22A—C20A −14.0 (4) O2B—N1B—C22B—C20B −18.9 (4)
C23A—N1A—C22A—C20A −165.5 (3) C23B—N1B—C22B—C20B −161.0 (3)
C17A—C20A—C22A—O1A 37.4 (4) C17B—C20B—C22B—O1B 27.8 (4)
C21A—C20A—C22A—O1A −87.2 (4) C21B—C20B—C22B—O1B −95.8 (4)
C17A—C20A—C22A—N1A −142.2 (3) C17B—C20B—C22B—N1B −150.7 (3)
C21A—C20A—C22A—N1A 93.2 (3) C21B—C20B—C22B—N1B 85.8 (3)
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Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A
O3A—H3A···O3Bi 0.86 (4) 1.93 (4) 2.782 (4) 180 (5)
O3B—H3B···O1Aii 0.83 (4) 1.95 (4) 2.768 (3) 169 (4)
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Symmetry codes: (i) −x+3/2, −y+1, z−1/2; (ii) −x+1, y−1/2, −z+3/2.

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989015001747/hb7343sup1.cif

e-71-00275-sup1.cif (1.3MB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015001747/hb7343Isup2.hkl

e-71-00275-Isup2.hkl (424KB, hkl)
Click here for additional data file. (9.7KB, cml)

Supporting information file. DOI: 10.1107/S2056989015001747/hb7343Isup3.cml

CCDC reference: 1045692

Additional supporting information: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Crystallographic Communications are provided here courtesy of International Union of Crystallography

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