In the title analogue of cholesterol, a new chain including an intermediate triazole and a tertiary hydroxyl group in the terminal position has been added at position 20, inducing a change in its stereochemistry.
Keywords: crystal structure, cholesterol, gemini, analogue, hydrogen bonding
Abstract
In the title cholesterol analogue, [systematic name: (3S,8S,9S,10R,13S,14S,17R)-17-{(S)-1-[4-(2-hydroxypropan-2-yl)-1H-1,2,3-triazol-1-yl]-6-methylheptan-2-yl}-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol] C32H53N3O2, a new chain, including an intermediate triazole and a tertiary hydroxyl group in the terminal position, has been added at position 20 inducing a change in its stereochemistry. In the crystal, molecules are linked by O—H⋯O and O—H⋯N hydrogen bonds, forming layers lying parallel to (-201) and enclosing R 4 4(36) ring motifs. The isopropyl group is disordered about two positions with a refined occupancy ratio of 0.763 (5):0.237 (5). A region of disordered electron density was corrected for using the SQUEEZE routine in PLATON (Spek (2015). Acta Cryst. C71, 9–18). The given chemical formula and other crystal data do not take into account the unknown solvent molecule(s).
Chemical context
The nuclear receptors (NRs) are a large family of ligand-regulated transcriptional factors and include the receptors for steroid hormones, thyroid hormones, lipophilic vitamins and cholesterol metabolites (Mangelsdorf & Evans, 1995 ▸; Burris et al., 2013 ▸). Approximately half of NRs are classified as orphan NRs because they do not have well-characterized ligands (Hummasti & Tontonoz, 2008 ▸). Orphan NRs are an active area of research partly due to their potential for clinical agent development for various diseases (Mohan & Heyman, 2003 ▸). Recent studies have demonstrated that retinoic acid receptor-related orphan receptors (RORs) have been implicated in several physiological and pathological processes.
Using the methodology developed in our research group for the synthesis of gemini-type vitamin D analogues (Fall et al., 2011 ▸; Pazos et al., 2016 ▸; Santalla et al., 2017 ▸) (modified with a double side chain), we can access new cholesterol analogues that can be of great interest in interactions with RORs. In this study, we present the structure of a new analogue of cholesterol (2), with eight stereocentres and a double side chain based on the aliphatic chain of cholesterol on the one hand and on the incorporation of a triazole ring on the other, since many azasteroids have proven to be biologically active. For example, some of them act as 5α-reductase inhibitors, antifungal agents and γ-aminobutyric acid (GABA) receptor modulators (Tian et al., 1995 ▸; Burbiel & Bracher, 2003 ▸; Covey et al., 2000 ▸).
Structural commentary
In the title cholesterol gemini-type analogue 2, illustrated in Fig. 1 ▸, the four aliphatic rings are structurally identical to those in the cholesterol hormone, i-cholesteryl methyl ether (Bernal et al., 1940 ▸; Wang et al., 2014 ▸). In the title compound, atom C20 has a different stereochemistry than in the cholesterol molecule, as a result of stereospecific reactions of the synthetic pathway. Furthermore, a new chain, including an intermediate triazole and a tertiary hydroxyl group in the terminal position, has been added at atom C21. Although some steroid analogues with a triazole ring have been synthesized (Seck et al., 2015 ▸), there are no references to any crystallographic analyses of gemini cholesterols with a triazole group at position C21 (Cambridge Structural Database, version 5.39, last update February 2018; Groom et al., 2016 ▸). The terminal OH group (C2′/C3′/O3′) is inclined to the triazole ring (N1′–N3′/C1′/C2′) mean plane by 7.2 (2) °.
Figure 1.
The molecular structure of compound 2, with the atom labelling. Displacement ellipsoids are drawn at the 30% probability level. In this and other figures the minor disorder component atoms (C24B–C27B) of the aliphatic chain at C20 have been omitted for clarity.
Supramolecular features
The molecular association in the title compound 2, is based on hydrogen bonding involving the hydroxyl and triazole groups (Table 1 ▸). These intermolecular links are present in the form of two chains. The first, a C(18) chain (Fig. 2 ▸), is formed by the O3—H3⋯O3’i hydrogen bond with O3—H3 acting as the donor and atom O3′ acting as the acceptor. The second is a C(5) chain, in which the triazole group participates, and is formed by hydrogen bond O3′—H3′⋯N3’ii (Fig. 3 ▸); the alcohol group O3′—H3′ acts as the donor towards the acceptor atom N3′. The combination of these interactions results in the formation of layers lying parallel to the (
01) plane, as shown in Fig. 4 ▸, and encloses 
(36) ring motifs, details of which are illustrated in Fig. 5 ▸.
Table 1. Hydrogen-bond geometry (Å, °).
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| O3—H3⋯O3′i | 0.84 | 2.00 | 2.811 (3) | 162 |
| O3′—H3′⋯N3′ii | 0.84 | 1.97 | 2.810 (2) | 175 |
Symmetry codes: (i) 
; (ii) 
.
Figure 2.
A view of the O—H⋯O hydrogen bonded C(18) chain propagating along the [102] direction (blue dashed lines; see Table 1 ▸).
Figure 3.
A view of the O—H⋯N hydrogen bonded C(5) chain propagating along the [010] direction (blue dashed lines; see Table 1 ▸).
Figure 4.
A view approximately normal to the (01) plane of the crystal packing of compound 2. Hydrogen bonds (see Table 1 ▸) are shown as dashed lines, and only H atoms H3 and H3′ have been included.
Figure 5.
A partial view of the crystal packing of compound 2, showing details of the O—H⋯O and O—H⋯N hydrogen bonds forming an (36) ring motif (blue dashed lines; see Table 1 ▸).
Synthesis and crystallization
Compound 2: details of the synthesis are illustrated in Fig. 6 ▸. To a solution of triazole 1 (12 mg, 0.022 mmol;) in tBuOH (2 ml) and water (1 ml) was added p-TsOH (5 mg) and the mixture was heated to 353 K for 3 h. The reaction mixture was diluted with water and then extracted with CH2Cl2 (3 × 5 ml). The combined organic layers were dried with Na2SO4, filtered, and concentrated. The residue was purified by flash column chromatography (50% EtOAc/hexane) to afford the title diol (11 mg, 99%). Compound 2 was recrystallized as colourless prisms by slow evaporation of a solvent mixture of dichloromethane/diethyl ether (1:1) at room temperature [yield 99%; m.p. 778 K; R f: 0.10 (30% EtOAc/hexane)].
Figure 6.
The synthesis of the title compound 2.
Spectroscopic data for 2: MS–ESI [m/z (%)]: 534.40 (10) [M + + Na], 512.42 (100) [M + + H], 494.41 (31) [M + − OMe]. 1H NMR (CDCl3, δ): 7.36 (1H, s, H-1′), 5.35 (1H, s, H-6), 4.32 (1H, m, H-21), 4.23 (1H, m, H-21), 3.52 (1H, m, H-3), 2.26 (3H, m), 1.94 (5H, m), 1.83 (5H, m), 1.48 (7H, m), 1.27 (4H, m), 1.23 (6H, d, J = 9.2 Hz, CH3-4′/5′), 1.06 (3H, m), 1.00 (3H, s, CH3-18), 0.84 (6H, d, J = 6.6 Hz, CH3-26/27), 0.73 (6H, s, CH3-19) ppm. 13C NMR (CDCl3, δ): 140.74 (C-5), 128.78 (C-2′), 121.51 (CH-6), 112.41 (C-1′), 77.20 (C-3′), 71.73 (CH-3), 56.38 (CH-14), 52.30 (CH2-21), 50.25 (CH), 49.99 (CH), 42.73 (C-13), 42.23 (CH2), 41.66 (CH), 39.20 (CH2), 39.16 (CH2), 37.23 (CH2), 36.48 (C-10), 31.93 (CH), 31.80 (CH2), 31.61 (CH2), 30.50 (CH3-4′/5′), 30.47 (CH3-4′/5′), 29.30 (CH2), 27.85 (CH2), 27.82 (CH), 24.26 (CH2), 22.69 (CH3-26/27), 22.52 (CH3-26/27), 22.38 (CH2), 21.07 (CH2), 19.37 (CH3-18), 12.08 (CH3-19) p.p.m.
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. The O—H and C-bound hydrogen atoms were positioned geometrically (O–H = 0.84 Å, C—H = 0.95–1.00 Å) and refined using a riding model with U iso(H) = 1.5U eq(O-hydroxyl, C-methyl) and 1.2U eq(C) for other H atoms. The isopropyl group is disordered about two positions with a refined occupancy ratio of 0.763 (5):0.237 (5) for atoms C24–C27/C24B–C27B.
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | C32H53N3O |
| M r | 511.77 |
| Crystal system, space group | Monoclinic, C2 |
| Temperature (K) | 100 |
| a, b, c (Å) | 20.1130 (15), 10.3898 (7), 15.5934 (12) |
| β (°) | 97.452 (2) |
| V (Å3) | 3231.0 (4) |
| Z | 4 |
| Radiation type | Mo Kα |
| μ (mm−1) | 0.07 |
| Crystal size (mm) | 0.35 × 0.30 × 0.24 |
| Data collection | |
| Diffractometer | Bruker D8 Venture Photon 100 CMOS |
| Absorption correction | Multi-scan (SADABS; Bruker, 2016 ▸) |
| T min, T max | 0.688, 0.746 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 85013, 8040, 7629 |
| R int | 0.029 |
| (sin θ/λ)max (Å−1) | 0.670 |
| Refinement | |
| R[F 2 > 2σ(F 2)], wR(F 2), S | 0.044, 0.122, 1.02 |
| No. of reflections | 8040 |
| No. of parameters | 363 |
| No. of restraints | 5 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.46, −0.31 |
| Absolute structure | Flack x determined using 3430 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons et al., 2013 ▸) |
| Absolute structure parameter | 0.1 (3) |
A region of disordered electron density was corrected for using the SQUEEZE routine in PLATON (Spek, 2015 ▸): volume ca 269 Å3 for 96 electrons count per unit cell. There is possibly one molecule of diethyl ether per molecule of the title compound 2. The formula mass and unit-cell characteristics were not taken into account during refinement.
Supplementary Material
Crystal structure: contains datablock(s) 2, Global. DOI: 10.1107/S2056989018003286/ex2005sup1.cif
CCDC reference: 1825767
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
The work of the MS and X-ray divisions of the research support service of the University of Vigo (CACTI) is gratefully acknowledged.
supplementary crystallographic information
Crystal data
| C32H53N3O | F(000) = 1128 |
| Mr = 511.77 | Dx = 1.052 Mg m−3 |
| Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
| a = 20.1130 (15) Å | Cell parameters from 9096 reflections |
| b = 10.3898 (7) Å | θ = 2.5–28.4° |
| c = 15.5934 (12) Å | µ = 0.07 mm−1 |
| β = 97.452 (2)° | T = 100 K |
| V = 3231.0 (4) Å3 | Prism, colourless |
| Z = 4 | 0.35 × 0.30 × 0.24 mm |
Data collection
| Bruker D8 Venture Photon 100 CMOS diffractometer | 7629 reflections with I > 2σ(I) |
| φ and ω scans | Rint = 0.029 |
| Absorption correction: multi-scan (SADABS; Bruker, 2016) | θmax = 28.4°, θmin = 2.5° |
| Tmin = 0.688, Tmax = 0.746 | h = −26→26 |
| 85013 measured reflections | k = −13→13 |
| 8040 independent reflections | l = −20→20 |
Refinement
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: mixed |
| R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
| wR(F2) = 0.122 | w = 1/[σ2(Fo2) + (0.0729P)2 + 1.6246P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.02 | (Δ/σ)max = 0.008 |
| 8040 reflections | Δρmax = 0.46 e Å−3 |
| 363 parameters | Δρmin = −0.31 e Å−3 |
| 5 restraints | Absolute structure: Flack x determined using 3430 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
| Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.1 (3) |
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 (Å2)
| x | y | z | Uiso*/Ueq | Occ. (<1) | |
| O3 | 0.35759 (11) | 0.2665 (4) | 0.82807 (13) | 0.0775 (9) | |
| H3 | 0.329808 | 0.292008 | 0.860194 | 0.116* | |
| O3' | −0.21535 (8) | −0.17225 (15) | −0.03536 (11) | 0.0324 (3) | |
| H3' | −0.246827 | −0.224255 | −0.031655 | 0.049* | |
| N1' | −0.07599 (8) | 0.09363 (17) | 0.07066 (10) | 0.0246 (3) | |
| N2' | −0.11583 (9) | 0.19700 (17) | 0.06509 (12) | 0.0296 (4) | |
| N3' | −0.17644 (9) | 0.15741 (18) | 0.03258 (12) | 0.0291 (4) | |
| C1 | 0.21530 (12) | 0.1479 (3) | 0.66464 (13) | 0.0399 (5) | |
| H1A | 0.168814 | 0.121675 | 0.670664 | 0.048* | |
| H1B | 0.238521 | 0.072198 | 0.643980 | 0.048* | |
| C1' | −0.11028 (11) | −0.0135 (2) | 0.04215 (12) | 0.0257 (4) | |
| H1' | −0.093554 | −0.098775 | 0.039622 | 0.031* | |
| C2 | 0.25074 (14) | 0.1869 (4) | 0.75364 (15) | 0.0538 (8) | |
| H2A | 0.226878 | 0.260248 | 0.776283 | 0.065* | |
| H2B | 0.250049 | 0.114006 | 0.794424 | 0.065* | |
| C2' | −0.17475 (10) | 0.02869 (19) | 0.01766 (12) | 0.0254 (4) | |
| C3 | 0.32250 (13) | 0.2246 (3) | 0.74675 (15) | 0.0472 (7) | |
| H3A | 0.346192 | 0.147179 | 0.727638 | 0.057* | |
| C3' | −0.23710 (11) | −0.0443 (2) | −0.01857 (14) | 0.0305 (4) | |
| C4 | 0.32511 (12) | 0.3296 (3) | 0.67895 (15) | 0.0388 (5) | |
| H4A | 0.307741 | 0.410699 | 0.700939 | 0.047* | |
| H4B | 0.372452 | 0.344304 | 0.670450 | 0.047* | |
| C4' | −0.28702 (14) | −0.0460 (3) | 0.0473 (2) | 0.0491 (7) | |
| H4'A | −0.328751 | −0.087103 | 0.021575 | 0.074* | |
| H4'B | −0.296399 | 0.042503 | 0.063909 | 0.074* | |
| H4'C | −0.267970 | −0.094362 | 0.098575 | 0.074* | |
| C5 | 0.28505 (10) | 0.2978 (2) | 0.59230 (13) | 0.0290 (4) | |
| C5' | −0.26936 (15) | 0.0171 (3) | −0.1032 (2) | 0.0484 (7) | |
| H5'A | −0.236719 | 0.019264 | −0.144712 | 0.073* | |
| H5'B | −0.283572 | 0.104994 | −0.091894 | 0.073* | |
| H5'C | −0.308430 | −0.033800 | −0.127195 | 0.073* | |
| C6 | 0.31207 (10) | 0.3053 (2) | 0.51844 (14) | 0.0313 (4) | |
| H6 | 0.358126 | 0.327892 | 0.522258 | 0.038* | |
| C7 | 0.27513 (10) | 0.2807 (2) | 0.43003 (13) | 0.0300 (4) | |
| H7A | 0.289590 | 0.196862 | 0.408602 | 0.036* | |
| H7B | 0.286977 | 0.348379 | 0.389965 | 0.036* | |
| C8 | 0.19900 (9) | 0.27924 (19) | 0.42977 (12) | 0.0231 (4) | |
| H8 | 0.182769 | 0.369334 | 0.435870 | 0.028* | |
| C9 | 0.18246 (9) | 0.1983 (2) | 0.50722 (11) | 0.0223 (3) | |
| H9 | 0.204785 | 0.113112 | 0.502406 | 0.027* | |
| C10 | 0.21297 (10) | 0.2561 (2) | 0.59538 (13) | 0.0275 (4) | |
| C11 | 0.10698 (10) | 0.1703 (2) | 0.50292 (12) | 0.0293 (4) | |
| H11A | 0.100051 | 0.107618 | 0.548748 | 0.035* | |
| H11B | 0.083522 | 0.250810 | 0.514914 | 0.035* | |
| C12 | 0.07549 (9) | 0.1166 (2) | 0.41518 (12) | 0.0257 (4) | |
| H12A | 0.026664 | 0.105256 | 0.415649 | 0.031* | |
| H12B | 0.095091 | 0.031154 | 0.405776 | 0.031* | |
| C13 | 0.08749 (9) | 0.20702 (19) | 0.34066 (11) | 0.0222 (3) | |
| C14 | 0.16431 (9) | 0.2218 (2) | 0.34556 (11) | 0.0237 (4) | |
| H14 | 0.182393 | 0.132477 | 0.342725 | 0.028* | |
| C15 | 0.17510 (11) | 0.2859 (2) | 0.26021 (13) | 0.0320 (4) | |
| H15A | 0.219280 | 0.262394 | 0.243283 | 0.038* | |
| H15B | 0.172312 | 0.380801 | 0.264597 | 0.038* | |
| C16 | 0.11729 (10) | 0.2325 (2) | 0.19454 (13) | 0.0300 (4) | |
| H16A | 0.135361 | 0.177939 | 0.150946 | 0.036* | |
| H16B | 0.091499 | 0.304031 | 0.164280 | 0.036* | |
| C17 | 0.07153 (8) | 0.1516 (2) | 0.24737 (11) | 0.0212 (3) | |
| H17 | 0.088297 | 0.060868 | 0.248789 | 0.025* | |
| C18 | 0.05172 (11) | 0.3366 (2) | 0.34758 (15) | 0.0333 (5) | |
| H18A | 0.056778 | 0.389264 | 0.296676 | 0.050* | |
| H18B | 0.071597 | 0.381738 | 0.399894 | 0.050* | |
| H18C | 0.003982 | 0.321512 | 0.350577 | 0.050* | |
| C19 | 0.17159 (14) | 0.3708 (3) | 0.62128 (19) | 0.0494 (7) | |
| H19A | 0.164581 | 0.432269 | 0.573271 | 0.074* | |
| H19B | 0.195719 | 0.413239 | 0.672214 | 0.074* | |
| H19C | 0.128087 | 0.340122 | 0.634875 | 0.074* | |
| C20 | −0.00253 (9) | 0.1494 (2) | 0.20600 (11) | 0.0231 (3) | |
| H20 | −0.019403 | 0.239995 | 0.205211 | 0.028* | |
| C21 | −0.00603 (9) | 0.1048 (2) | 0.11160 (12) | 0.0265 (4) | |
| H21A | 0.018056 | 0.167241 | 0.078850 | 0.032* | |
| H21B | 0.016486 | 0.020320 | 0.109684 | 0.032* | |
| C22 | −0.04890 (9) | 0.0678 (2) | 0.25508 (12) | 0.0255 (4) | |
| H22A | −0.048827 | 0.105022 | 0.313526 | 0.031* | |
| H22B | −0.095151 | 0.074933 | 0.224772 | 0.031* | |
| C23 | −0.03115 (10) | −0.0746 (2) | 0.26492 (14) | 0.0304 (4) | |
| H23A | 0.016646 | −0.084771 | 0.288671 | 0.036* | |
| H23B | −0.038774 | −0.118011 | 0.207982 | 0.036* | |
| C24 | −0.0767 (2) | −0.1347 (4) | 0.3276 (2) | 0.0389 (7) | 0.763 (5) |
| H24A | −0.066712 | −0.092988 | 0.384918 | 0.047* | 0.763 (5) |
| H24B | −0.124162 | −0.116555 | 0.305481 | 0.047* | 0.763 (5) |
| C25 | −0.06732 (19) | −0.2815 (4) | 0.3385 (3) | 0.0428 (8) | 0.763 (5) |
| H25 | −0.093048 | −0.306183 | 0.386759 | 0.051* | 0.763 (5) |
| C26 | 0.0043 (3) | −0.3176 (4) | 0.3687 (5) | 0.0768 (17) | 0.763 (5) |
| H26A | 0.023690 | −0.255904 | 0.412492 | 0.115* | 0.763 (5) |
| H26B | 0.030030 | −0.316282 | 0.319486 | 0.115* | 0.763 (5) |
| H26C | 0.005819 | −0.404206 | 0.393806 | 0.115* | 0.763 (5) |
| C27 | −0.0969 (3) | −0.3579 (8) | 0.2627 (4) | 0.0667 (14) | 0.763 (5) |
| H27A | −0.069611 | −0.347475 | 0.215460 | 0.100* | 0.763 (5) |
| H27B | −0.142641 | −0.327817 | 0.243705 | 0.100* | 0.763 (5) |
| H27C | −0.098069 | −0.449028 | 0.278740 | 0.100* | 0.763 (5) |
| C24B | −0.0510 (7) | −0.1677 (11) | 0.3327 (8) | 0.0389 (7) | 0.237 (5) |
| H24B | −0.028169 | −0.138464 | 0.389453 | 0.047* | 0.237 (5) |
| H24A | −0.099715 | −0.156564 | 0.334308 | 0.047* | 0.237 (5) |
| C25B | −0.0384 (7) | −0.3100 (11) | 0.3271 (8) | 0.0428 (8) | 0.237 (5) |
| H25 | 0.008894 | −0.317481 | 0.314094 | 0.051* | 0.237 (5) |
| C26B | −0.0377 (6) | −0.3632 (17) | 0.4122 (10) | 0.073 (5) | 0.237 (5) |
| H26A | −0.079316 | −0.340174 | 0.434835 | 0.109* | 0.237 (5) |
| H26B | 0.000683 | −0.328578 | 0.450387 | 0.109* | 0.237 (5) |
| H26C | −0.033923 | −0.457077 | 0.409337 | 0.109* | 0.237 (5) |
| C27B | −0.0815 (13) | −0.359 (3) | 0.2463 (14) | 0.0667 (14) | 0.237 (5) |
| H27A | −0.098369 | −0.285928 | 0.210137 | 0.100* | 0.237 (5) |
| H27B | −0.119378 | −0.408162 | 0.262993 | 0.100* | 0.237 (5) |
| H27C | −0.054504 | −0.414775 | 0.213602 | 0.100* | 0.237 (5) |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O3 | 0.0457 (11) | 0.155 (3) | 0.0296 (9) | −0.0415 (15) | −0.0044 (8) | −0.0143 (13) |
| O3' | 0.0347 (8) | 0.0252 (7) | 0.0361 (8) | −0.0052 (6) | 0.0007 (6) | −0.0033 (6) |
| N1' | 0.0255 (8) | 0.0276 (8) | 0.0197 (7) | 0.0004 (7) | −0.0010 (6) | 0.0009 (6) |
| N2' | 0.0305 (9) | 0.0242 (8) | 0.0308 (8) | 0.0007 (7) | −0.0081 (7) | 0.0003 (7) |
| N3' | 0.0286 (8) | 0.0239 (8) | 0.0315 (8) | 0.0002 (7) | −0.0087 (7) | 0.0007 (7) |
| C1 | 0.0368 (11) | 0.0615 (15) | 0.0200 (9) | −0.0227 (11) | −0.0010 (8) | 0.0035 (10) |
| C1' | 0.0320 (10) | 0.0240 (9) | 0.0206 (8) | 0.0007 (7) | 0.0009 (7) | −0.0010 (7) |
| C2 | 0.0421 (13) | 0.097 (2) | 0.0215 (10) | −0.0329 (14) | −0.0009 (9) | 0.0020 (12) |
| C2' | 0.0296 (10) | 0.0249 (9) | 0.0205 (8) | −0.0011 (7) | −0.0017 (7) | 0.0010 (7) |
| C3 | 0.0368 (12) | 0.079 (2) | 0.0243 (10) | −0.0214 (13) | −0.0031 (9) | −0.0042 (11) |
| C3' | 0.0305 (10) | 0.0242 (10) | 0.0351 (10) | −0.0036 (8) | −0.0025 (8) | −0.0032 (8) |
| C4 | 0.0298 (10) | 0.0524 (14) | 0.0333 (11) | −0.0169 (10) | 0.0006 (8) | −0.0112 (10) |
| C4' | 0.0425 (14) | 0.0390 (13) | 0.0687 (18) | −0.0098 (11) | 0.0181 (13) | −0.0177 (13) |
| C5 | 0.0233 (9) | 0.0337 (11) | 0.0293 (9) | −0.0103 (8) | 0.0010 (7) | −0.0031 (8) |
| C5' | 0.0464 (14) | 0.0374 (13) | 0.0533 (15) | −0.0052 (10) | −0.0250 (12) | 0.0007 (11) |
| C6 | 0.0219 (9) | 0.0403 (12) | 0.0314 (10) | −0.0115 (8) | 0.0020 (7) | −0.0001 (8) |
| C7 | 0.0220 (9) | 0.0415 (11) | 0.0267 (9) | −0.0094 (8) | 0.0042 (7) | 0.0023 (8) |
| C8 | 0.0203 (8) | 0.0254 (9) | 0.0237 (8) | −0.0046 (7) | 0.0032 (6) | 0.0016 (7) |
| C9 | 0.0196 (8) | 0.0296 (9) | 0.0179 (7) | −0.0062 (7) | 0.0032 (6) | −0.0027 (7) |
| C10 | 0.0235 (9) | 0.0367 (11) | 0.0223 (8) | −0.0075 (8) | 0.0032 (7) | −0.0060 (8) |
| C11 | 0.0211 (8) | 0.0483 (13) | 0.0190 (8) | −0.0097 (8) | 0.0048 (6) | −0.0028 (8) |
| C12 | 0.0198 (8) | 0.0396 (11) | 0.0178 (8) | −0.0082 (7) | 0.0029 (6) | 0.0010 (7) |
| C13 | 0.0190 (8) | 0.0292 (9) | 0.0184 (7) | −0.0006 (7) | 0.0026 (6) | 0.0003 (7) |
| C14 | 0.0195 (8) | 0.0331 (10) | 0.0190 (8) | −0.0041 (7) | 0.0041 (6) | 0.0017 (7) |
| C15 | 0.0278 (9) | 0.0457 (12) | 0.0229 (9) | −0.0083 (9) | 0.0040 (7) | 0.0066 (8) |
| C16 | 0.0257 (9) | 0.0430 (12) | 0.0215 (8) | −0.0027 (8) | 0.0042 (7) | 0.0063 (8) |
| C17 | 0.0181 (8) | 0.0287 (9) | 0.0171 (7) | 0.0013 (7) | 0.0032 (6) | 0.0018 (7) |
| C18 | 0.0301 (10) | 0.0339 (11) | 0.0349 (10) | 0.0067 (9) | 0.0007 (8) | −0.0065 (9) |
| C19 | 0.0378 (13) | 0.0621 (17) | 0.0473 (14) | 0.0038 (12) | 0.0023 (11) | −0.0304 (13) |
| C20 | 0.0196 (8) | 0.0314 (9) | 0.0179 (7) | 0.0026 (7) | 0.0008 (6) | 0.0004 (7) |
| C21 | 0.0218 (8) | 0.0377 (10) | 0.0196 (8) | −0.0001 (8) | 0.0015 (6) | −0.0010 (8) |
| C22 | 0.0169 (8) | 0.0391 (11) | 0.0205 (8) | 0.0018 (7) | 0.0026 (6) | −0.0010 (7) |
| C23 | 0.0230 (9) | 0.0369 (11) | 0.0312 (10) | −0.0016 (8) | 0.0031 (7) | 0.0063 (8) |
| C24 | 0.037 (2) | 0.0354 (18) | 0.0487 (16) | 0.0075 (13) | 0.0199 (15) | 0.0068 (13) |
| C25 | 0.0342 (19) | 0.0376 (17) | 0.0599 (19) | −0.0024 (14) | 0.0192 (15) | 0.0051 (14) |
| C26 | 0.057 (3) | 0.043 (2) | 0.129 (5) | 0.0094 (19) | 0.006 (3) | 0.025 (3) |
| C27 | 0.080 (4) | 0.072 (2) | 0.053 (3) | −0.037 (3) | 0.029 (2) | −0.010 (2) |
| C24B | 0.037 (2) | 0.0354 (18) | 0.0487 (16) | 0.0075 (13) | 0.0199 (15) | 0.0068 (13) |
| C25B | 0.0342 (19) | 0.0376 (17) | 0.0599 (19) | −0.0024 (14) | 0.0192 (15) | 0.0051 (14) |
| C26B | 0.027 (5) | 0.086 (11) | 0.103 (12) | 0.012 (6) | −0.003 (6) | −0.044 (10) |
| C27B | 0.080 (4) | 0.072 (2) | 0.053 (3) | −0.037 (3) | 0.029 (2) | −0.010 (2) |
Geometric parameters (Å, º)
| O3—C3 | 1.437 (3) | C13—C17 | 1.559 (2) |
| O3—H3 | 0.8400 | C14—C15 | 1.529 (3) |
| O3'—C3' | 1.434 (3) | C14—H14 | 1.0000 |
| O3'—H3' | 0.8400 | C15—C16 | 1.549 (3) |
| N1'—N2' | 1.336 (2) | C15—H15A | 0.9900 |
| N1'—C1' | 1.354 (3) | C15—H15B | 0.9900 |
| N1'—C21 | 1.472 (2) | C16—C17 | 1.559 (3) |
| N2'—N3' | 1.324 (2) | C16—H16A | 0.9900 |
| N3'—C2' | 1.359 (3) | C16—H16B | 0.9900 |
| C1—C2 | 1.530 (3) | C17—C20 | 1.545 (2) |
| C1—C10 | 1.555 (3) | C17—H17 | 1.0000 |
| C1—H1A | 0.9900 | C18—H18A | 0.9800 |
| C1—H1B | 0.9900 | C18—H18B | 0.9800 |
| C1'—C2' | 1.375 (3) | C18—H18C | 0.9800 |
| C1'—H1' | 0.9500 | C19—H19A | 0.9800 |
| C2—C3 | 1.513 (3) | C19—H19B | 0.9800 |
| C2—H2A | 0.9900 | C19—H19C | 0.9800 |
| C2—H2B | 0.9900 | C20—C21 | 1.536 (3) |
| C2'—C3' | 1.511 (3) | C20—C22 | 1.536 (3) |
| C3—C4 | 1.525 (4) | C20—H20 | 1.0000 |
| C3—H3A | 1.0000 | C21—H21A | 0.9900 |
| C3'—C4' | 1.526 (4) | C21—H21B | 0.9900 |
| C3'—C5' | 1.532 (3) | C22—C23 | 1.525 (3) |
| C4—C5 | 1.517 (3) | C22—H22A | 0.9900 |
| C4—H4A | 0.9900 | C22—H22B | 0.9900 |
| C4—H4B | 0.9900 | C23—C24B | 1.524 (11) |
| C4'—H4'A | 0.9800 | C23—C24 | 1.554 (4) |
| C4'—H4'B | 0.9800 | C23—H23A | 0.9901 |
| C4'—H4'C | 0.9800 | C23—H23B | 0.9899 |
| C5—C6 | 1.338 (3) | C24—C25 | 1.544 (5) |
| C5—C10 | 1.520 (3) | C24—H24A | 0.9900 |
| C5'—H5'A | 0.9800 | C24—H24B | 0.9900 |
| C5'—H5'B | 0.9800 | C25—C27 | 1.484 (7) |
| C5'—H5'C | 0.9800 | C25—C26 | 1.504 (6) |
| C6—C7 | 1.501 (3) | C25—H25 | 1.0000 |
| C6—H6 | 0.9500 | C26—H26A | 0.9800 |
| C7—C8 | 1.531 (3) | C26—H26B | 0.9800 |
| C7—H7A | 0.9900 | C26—H26C | 0.9800 |
| C7—H7B | 0.9900 | C27—H27A | 0.9800 |
| C8—C14 | 1.526 (3) | C27—H27B | 0.9800 |
| C8—C9 | 1.543 (3) | C27—H27C | 0.9800 |
| C8—H8 | 1.0000 | C24B—C25B | 1.504 (15) |
| C9—C11 | 1.539 (3) | C24B—H24B | 0.9900 |
| C9—C10 | 1.552 (2) | C24B—H24A | 0.9900 |
| C9—H9 | 1.0000 | C25B—C26B | 1.436 (19) |
| C10—C19 | 1.538 (3) | C25B—C27B | 1.52 (2) |
| C11—C12 | 1.536 (3) | C25B—H25 | 1.0000 |
| C11—H11A | 0.9900 | C26B—H26A | 0.9800 |
| C11—H11B | 0.9900 | C26B—H26B | 0.9800 |
| C12—C13 | 1.537 (3) | C26B—H26C | 0.9800 |
| C12—H12A | 0.9900 | C27B—H27A | 0.9800 |
| C12—H12B | 0.9900 | C27B—H27B | 0.9800 |
| C13—C18 | 1.537 (3) | C27B—H27C | 0.9800 |
| C13—C14 | 1.545 (2) | ||
| C3—O3—H3 | 109.5 | C15—C14—H14 | 105.8 |
| C3'—O3'—H3' | 109.5 | C13—C14—H14 | 105.8 |
| N2'—N1'—C1' | 111.34 (16) | C14—C15—C16 | 103.90 (16) |
| N2'—N1'—C21 | 119.75 (17) | C14—C15—H15A | 111.0 |
| C1'—N1'—C21 | 128.66 (18) | C16—C15—H15A | 111.0 |
| N3'—N2'—N1' | 106.85 (16) | C14—C15—H15B | 111.0 |
| N2'—N3'—C2' | 109.22 (17) | C16—C15—H15B | 111.0 |
| C2—C1—C10 | 114.0 (2) | H15A—C15—H15B | 109.0 |
| C2—C1—H1A | 108.7 | C15—C16—C17 | 106.74 (15) |
| C10—C1—H1A | 108.7 | C15—C16—H16A | 110.4 |
| C2—C1—H1B | 108.7 | C17—C16—H16A | 110.4 |
| C10—C1—H1B | 108.7 | C15—C16—H16B | 110.4 |
| H1A—C1—H1B | 107.6 | C17—C16—H16B | 110.4 |
| N1'—C1'—C2' | 104.51 (18) | H16A—C16—H16B | 108.6 |
| N1'—C1'—H1' | 127.7 | C20—C17—C16 | 112.98 (15) |
| C2'—C1'—H1' | 127.7 | C20—C17—C13 | 117.75 (14) |
| C3—C2—C1 | 109.9 (2) | C16—C17—C13 | 103.26 (15) |
| C3—C2—H2A | 109.7 | C20—C17—H17 | 107.4 |
| C1—C2—H2A | 109.7 | C16—C17—H17 | 107.4 |
| C3—C2—H2B | 109.7 | C13—C17—H17 | 107.4 |
| C1—C2—H2B | 109.7 | C13—C18—H18A | 109.5 |
| H2A—C2—H2B | 108.2 | C13—C18—H18B | 109.5 |
| N3'—C2'—C1' | 108.07 (18) | H18A—C18—H18B | 109.5 |
| N3'—C2'—C3' | 121.33 (19) | C13—C18—H18C | 109.5 |
| C1'—C2'—C3' | 130.60 (19) | H18A—C18—H18C | 109.5 |
| O3—C3—C2 | 112.3 (2) | H18B—C18—H18C | 109.5 |
| O3—C3—C4 | 109.8 (2) | C10—C19—H19A | 109.5 |
| C2—C3—C4 | 110.7 (2) | C10—C19—H19B | 109.5 |
| O3—C3—H3A | 108.0 | H19A—C19—H19B | 109.5 |
| C2—C3—H3A | 108.0 | C10—C19—H19C | 109.5 |
| C4—C3—H3A | 108.0 | H19A—C19—H19C | 109.5 |
| O3'—C3'—C2' | 105.98 (17) | H19B—C19—H19C | 109.5 |
| O3'—C3'—C4' | 110.79 (19) | C21—C20—C22 | 110.83 (17) |
| C2'—C3'—C4' | 109.92 (19) | C21—C20—C17 | 109.05 (14) |
| O3'—C3'—C5' | 109.48 (19) | C22—C20—C17 | 114.50 (15) |
| C2'—C3'—C5' | 110.59 (19) | C21—C20—H20 | 107.4 |
| C4'—C3'—C5' | 110.0 (2) | C22—C20—H20 | 107.4 |
| C5—C4—C3 | 113.54 (19) | C17—C20—H20 | 107.4 |
| C5—C4—H4A | 108.9 | N1'—C21—C20 | 111.20 (15) |
| C3—C4—H4A | 108.9 | N1'—C21—H21A | 109.4 |
| C5—C4—H4B | 108.9 | C20—C21—H21A | 109.4 |
| C3—C4—H4B | 108.9 | N1'—C21—H21B | 109.4 |
| H4A—C4—H4B | 107.7 | C20—C21—H21B | 109.4 |
| C3'—C4'—H4'A | 109.5 | H21A—C21—H21B | 108.0 |
| C3'—C4'—H4'B | 109.5 | C23—C22—C20 | 115.88 (16) |
| H4'A—C4'—H4'B | 109.5 | C23—C22—H22A | 108.3 |
| C3'—C4'—H4'C | 109.5 | C20—C22—H22A | 108.3 |
| H4'A—C4'—H4'C | 109.5 | C23—C22—H22B | 108.3 |
| H4'B—C4'—H4'C | 109.5 | C20—C22—H22B | 108.3 |
| C6—C5—C4 | 121.72 (18) | H22A—C22—H22B | 107.4 |
| C6—C5—C10 | 122.64 (18) | C24B—C23—C22 | 127.3 (5) |
| C4—C5—C10 | 115.64 (18) | C22—C23—C24 | 107.7 (2) |
| C3'—C5'—H5'A | 109.5 | C24B—C23—H23A | 90.1 |
| C3'—C5'—H5'B | 109.5 | C22—C23—H23A | 110.2 |
| H5'A—C5'—H5'B | 109.5 | C24—C23—H23A | 110.2 |
| C3'—C5'—H5'C | 109.5 | C24B—C23—H23B | 108.0 |
| H5'A—C5'—H5'C | 109.5 | C22—C23—H23B | 110.2 |
| H5'B—C5'—H5'C | 109.5 | C24—C23—H23B | 110.2 |
| C5—C6—C7 | 124.95 (18) | H23A—C23—H23B | 108.5 |
| C5—C6—H6 | 117.5 | C25—C24—C23 | 113.1 (3) |
| C7—C6—H6 | 117.5 | C25—C24—H24A | 109.0 |
| C6—C7—C8 | 112.33 (17) | C23—C24—H24A | 109.0 |
| C6—C7—H7A | 109.1 | C25—C24—H24B | 109.0 |
| C8—C7—H7A | 109.1 | C23—C24—H24B | 109.0 |
| C6—C7—H7B | 109.1 | H24A—C24—H24B | 107.8 |
| C8—C7—H7B | 109.1 | C27—C25—C26 | 112.6 (5) |
| H7A—C7—H7B | 107.9 | C27—C25—C24 | 114.2 (5) |
| C14—C8—C7 | 110.59 (16) | C26—C25—C24 | 112.3 (3) |
| C14—C8—C9 | 109.85 (15) | C27—C25—H25 | 105.6 |
| C7—C8—C9 | 108.69 (16) | C26—C25—H25 | 105.6 |
| C14—C8—H8 | 109.2 | C24—C25—H25 | 105.6 |
| C7—C8—H8 | 109.2 | C25—C26—H26A | 109.5 |
| C9—C8—H8 | 109.2 | C25—C26—H26B | 109.5 |
| C11—C9—C8 | 112.38 (15) | H26A—C26—H26B | 109.5 |
| C11—C9—C10 | 112.73 (15) | C25—C26—H26C | 109.5 |
| C8—C9—C10 | 112.47 (15) | H26A—C26—H26C | 109.5 |
| C11—C9—H9 | 106.2 | H26B—C26—H26C | 109.5 |
| C8—C9—H9 | 106.2 | C25—C27—H27A | 109.5 |
| C10—C9—H9 | 106.2 | C25—C27—H27B | 109.5 |
| C5—C10—C19 | 109.78 (19) | H27A—C27—H27B | 109.5 |
| C5—C10—C9 | 110.59 (15) | C25—C27—H27C | 109.5 |
| C19—C10—C9 | 111.55 (18) | H27A—C27—H27C | 109.5 |
| C5—C10—C1 | 106.57 (17) | H27B—C27—H27C | 109.5 |
| C19—C10—C1 | 110.3 (2) | C25B—C24B—C23 | 121.4 (9) |
| C9—C10—C1 | 107.97 (17) | C25B—C24B—H24B | 107.0 |
| C12—C11—C9 | 113.46 (15) | C23—C24B—H24B | 107.0 |
| C12—C11—H11A | 108.9 | C25B—C24B—H24A | 107.0 |
| C9—C11—H11A | 108.9 | C23—C24B—H24A | 107.0 |
| C12—C11—H11B | 108.9 | H24B—C24B—H24A | 106.7 |
| C9—C11—H11B | 108.9 | C26B—C25B—C24B | 107.8 (12) |
| H11A—C11—H11B | 107.7 | C26B—C25B—C27B | 124.9 (14) |
| C11—C12—C13 | 111.36 (16) | C24B—C25B—C27B | 107.2 (17) |
| C11—C12—H12A | 109.4 | C26B—C25B—H25 | 105.1 |
| C13—C12—H12A | 109.4 | C24B—C25B—H25 | 105.1 |
| C11—C12—H12B | 109.4 | C27B—C25B—H25 | 105.1 |
| C13—C12—H12B | 109.4 | C25B—C26B—H26A | 109.5 |
| H12A—C12—H12B | 108.0 | C25B—C26B—H26B | 109.5 |
| C18—C13—C12 | 111.19 (16) | H26A—C26B—H26B | 109.5 |
| C18—C13—C14 | 112.56 (17) | C25B—C26B—H26C | 109.5 |
| C12—C13—C14 | 106.11 (14) | H26A—C26B—H26C | 109.5 |
| C18—C13—C17 | 110.35 (16) | H26B—C26B—H26C | 109.5 |
| C12—C13—C17 | 116.48 (16) | C25B—C27B—H27A | 109.5 |
| C14—C13—C17 | 99.58 (14) | C25B—C27B—H27B | 109.5 |
| C8—C14—C15 | 118.56 (17) | H27A—C27B—H27B | 109.5 |
| C8—C14—C13 | 115.10 (15) | C25B—C27B—H27C | 109.5 |
| C15—C14—C13 | 104.73 (15) | H27A—C27B—H27C | 109.5 |
| C8—C14—H14 | 105.8 | H27B—C27B—H27C | 109.5 |
| C1'—N1'—N2'—N3' | −0.2 (2) | C8—C9—C11—C12 | 50.0 (2) |
| C21—N1'—N2'—N3' | −174.88 (16) | C10—C9—C11—C12 | 178.37 (18) |
| N1'—N2'—N3'—C2' | 0.0 (2) | C9—C11—C12—C13 | −55.9 (2) |
| N2'—N1'—C1'—C2' | 0.2 (2) | C11—C12—C13—C18 | −64.8 (2) |
| C21—N1'—C1'—C2' | 174.35 (17) | C11—C12—C13—C14 | 57.9 (2) |
| C10—C1—C2—C3 | −59.8 (4) | C11—C12—C13—C17 | 167.62 (16) |
| N2'—N3'—C2'—C1' | 0.1 (2) | C7—C8—C14—C15 | −58.9 (2) |
| N2'—N3'—C2'—C3' | 179.24 (18) | C9—C8—C14—C15 | −178.86 (17) |
| N1'—C1'—C2'—N3' | −0.2 (2) | C7—C8—C14—C13 | 176.05 (17) |
| N1'—C1'—C2'—C3' | −179.2 (2) | C9—C8—C14—C13 | 56.1 (2) |
| C1—C2—C3—O3 | 177.9 (3) | C18—C13—C14—C8 | 61.5 (2) |
| C1—C2—C3—C4 | 54.9 (4) | C12—C13—C14—C8 | −60.4 (2) |
| N3'—C2'—C3'—O3' | 173.26 (18) | C17—C13—C14—C8 | 178.33 (16) |
| C1'—C2'—C3'—O3' | −7.8 (3) | C18—C13—C14—C15 | −70.5 (2) |
| N3'—C2'—C3'—C4' | −67.0 (3) | C12—C13—C14—C15 | 167.64 (17) |
| C1'—C2'—C3'—C4' | 111.9 (3) | C17—C13—C14—C15 | 46.35 (19) |
| N3'—C2'—C3'—C5' | 54.7 (3) | C8—C14—C15—C16 | −162.71 (18) |
| C1'—C2'—C3'—C5' | −126.4 (3) | C13—C14—C15—C16 | −32.7 (2) |
| O3—C3—C4—C5 | −175.9 (2) | C14—C15—C16—C17 | 5.9 (2) |
| C2—C3—C4—C5 | −51.3 (3) | C15—C16—C17—C20 | 150.76 (18) |
| C3—C4—C5—C6 | −128.2 (3) | C15—C16—C17—C13 | 22.5 (2) |
| C3—C4—C5—C10 | 51.2 (3) | C18—C13—C17—C20 | −48.0 (2) |
| C4—C5—C6—C7 | −177.4 (2) | C12—C13—C17—C20 | 80.0 (2) |
| C10—C5—C6—C7 | 3.2 (4) | C14—C13—C17—C20 | −166.57 (17) |
| C5—C6—C7—C8 | 14.6 (3) | C18—C13—C17—C16 | 77.23 (19) |
| C6—C7—C8—C14 | −165.92 (18) | C12—C13—C17—C16 | −154.78 (16) |
| C6—C7—C8—C9 | −45.3 (2) | C14—C13—C17—C16 | −41.30 (18) |
| C14—C8—C9—C11 | −48.2 (2) | C16—C17—C20—C21 | 53.8 (2) |
| C7—C8—C9—C11 | −169.37 (17) | C13—C17—C20—C21 | 174.09 (17) |
| C14—C8—C9—C10 | −176.74 (16) | C16—C17—C20—C22 | 178.58 (17) |
| C7—C8—C9—C10 | 62.1 (2) | C13—C17—C20—C22 | −61.1 (2) |
| C6—C5—C10—C19 | −111.7 (3) | N2'—N1'—C21—C20 | 59.8 (2) |
| C4—C5—C10—C19 | 68.8 (3) | C1'—N1'—C21—C20 | −113.9 (2) |
| C6—C5—C10—C9 | 11.8 (3) | C22—C20—C21—N1' | 49.7 (2) |
| C4—C5—C10—C9 | −167.7 (2) | C17—C20—C21—N1' | 176.60 (17) |
| C6—C5—C10—C1 | 128.9 (2) | C21—C20—C22—C23 | 63.9 (2) |
| C4—C5—C10—C1 | −50.6 (3) | C17—C20—C22—C23 | −60.0 (2) |
| C11—C9—C10—C5 | −172.73 (18) | C20—C22—C23—C24B | 157.7 (7) |
| C8—C9—C10—C5 | −44.4 (2) | C20—C22—C23—C24 | 171.5 (2) |
| C11—C9—C10—C19 | −50.3 (3) | C22—C23—C24—C25 | 176.0 (3) |
| C8—C9—C10—C19 | 78.0 (2) | C23—C24—C25—C27 | −73.4 (4) |
| C11—C9—C10—C1 | 71.0 (2) | C23—C24—C25—C26 | 56.4 (5) |
| C8—C9—C10—C1 | −160.65 (18) | C22—C23—C24B—C25B | 171.1 (8) |
| C2—C1—C10—C5 | 55.4 (3) | C23—C24B—C25B—C26B | 158.2 (11) |
| C2—C1—C10—C19 | −63.7 (3) | C23—C24B—C25B—C27B | −65.1 (15) |
| C2—C1—C10—C9 | 174.2 (2) |
Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| O3—H3···O3′i | 0.84 | 2.00 | 2.811 (3) | 162 |
| O3′—H3′···N3′ii | 0.84 | 1.97 | 2.810 (2) | 175 |
Symmetry codes: (i) x+1/2, y+1/2, z+1; (ii) −x−1/2, y−1/2, −z.
References
- Bernal, J. D., Crowfoot, D. & Fankuchen, I. (1940). Philos. Trans. Roy. Soc. A: Math. Phys. Engineering Sci. 239, 135–182.
- Bruker (2016). APEX3, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
- Burbiel, J. & Bracher, F. (2003). Steroids, 68, 587–594. [DOI] [PubMed]
- Burris, T. P., Solt, L. A., Wang, Y., Crumbley, C., Banerjee, S., Griffett, K., Lundasen, T., Hughes, T. & Kojetin, D. J. (2013). Pharmacol. Rev. 65, 710–778. [DOI] [PMC free article] [PubMed]
- Covey, D. F., Han, M., Kumar, A. S., de la Cruz, M. A. M., Meadows, E. S., Hu, Y., Tonnies, A., Nathan, D., Coleman, M., Benz, A., Evers, A. S., Zorumski, C. F. & Mennerick, S. (2000). J. Med. Chem. 43, 3201–3204. [DOI] [PubMed]
- Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341.
- Fall, Y., Gómez, G., Pérez, M., Gándara, Z., Pérez, X., Pazos, G. & Kurz, G. (2011). PCT Int. Appl. WO2011121152A120111006.
- Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. [DOI] [PMC free article] [PubMed]
- Hummasti, S. & Tontonoz, P. (2008). Mol. Endocrinol. 22, 1743–1753. [DOI] [PMC free article] [PubMed]
- Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.
- Mangelsdorf, D. J. & Evans, R. M. (1995). Cell, 83, 841–850. [DOI] [PubMed]
- Mohan, R. & Heyman, R. A. (2003). Curr. Top. Med. Chem. 3, 1637–1647. [DOI] [PubMed]
- Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249–259. [DOI] [PMC free article] [PubMed]
- Pazos, G., Pérez, M., Gándara, Z., Gómez, G. & Fall, Y. (2016). RSC Adv. 6, 61073–61076.
- Santalla, H., Martínez, A., Garrido, F., Gómez, G. & Fall, Y. (2017). Org. Chem. Front. 4, 1999–2001.
- Seck, I., Fall, A., Lago, C., Sène, M., Gaye, M., Seck, M., Gómez, G. & Fall, Y. (2015). Synthesis, 47, 2826–2830.
- Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.
- Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.
- Spek, A. L. (2009). Acta Cryst. D65, 148–155. [DOI] [PMC free article] [PubMed]
- Spek, A. L. (2015). Acta Cryst. C71, 9–18. [DOI] [PubMed]
- Tian, G., Mook, R., Moss, M. L. & Frye, S. V. (1995). Biochemistry, 34, 13453–13459. [DOI] [PubMed]
- Wang, J.-R., Zhou, C., Yu, X. & Mei, X. (2014). Chem. Commun. 50, 855–858. [DOI] [PubMed]
- Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.
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) 2, Global. DOI: 10.1107/S2056989018003286/ex2005sup1.cif
CCDC reference: 1825767
Additional supporting information: crystallographic information; 3D view; checkCIF report