Literature DB >> 35974826

Synthesis, characterization, crystal structure and Hirshfeld surface analysis of a hexa-hydro-quinoline derivative: tert-butyl 4-([1,1'-biphen-yl]-4-yl)-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexa-hydro-quinoline-3-carboxyl-ate.

Sema Öztürk Yıldırım1,2, Mehmet Akkurt2, Gökalp Çetin3,4, Rahime Şimşek4, Ray J Butcher5, Ajaya Bhattarai6.   

Abstract

The title compound, C29H33NO3, crystallizes with three mol-ecules (A, B and C) in the asymmetric unit. They differ in the twist of the phenyl and benzene rings of the 1,1'-biphenyl ring with respect to the plane of the 1,4-di-hydro-pyridine ring. In all three mol-ecules, the 1,4-di-hydro-pyridine ring adopts a distorted boat conformation. The cyclo-hexene ring has an envelope conformation in mol-ecules A and B, while it exhibits a distorted half-chair conformation for both the major and minor components in the disordered mol-ecule C. In the crystal, mol-ecules are linked by C-H⋯O and N-H⋯O hydrogen bonds, forming layers parallel to (100) defining R 1 4(6) and C(7) graph-set motifs. Additional C-H⋯π inter-actions consolidate the layered structure. Between the layers, van der Waals inter-actions stabilize the packing, as revealed by Hirshfeld surface analysis. The greatest contributions to the crystal packing are from H⋯H (69.6% in A, 69.9% in B, 70.1% in C), C⋯H/H⋯C (20.3% in A, 20.6% in B, 20.3% in C) and O⋯H/H⋯O (8.6% in A, 8.6% in B, 8.4% in C) inter-actions. © Yıldırım et al. 2022.

Entities:  

Keywords:  1,4-di­hydro­pyridine ring; Hirshfeld surface analysis; crystal structure; cyclo­hexene ring; disorder; quinoline ring system; van der Waals inter­actions

Year:  2022        PMID： 35974826      PMCID： PMC9361379          DOI： 10.1107/S2056989022007022

Source DB:  PubMed          Journal:  Acta Crystallogr E Crystallogr Commun


Chemical context

Chronic diseases are among the most common causes of death in the world, accompanied by difficulties and costs in treatment and health care. Therefore, preventing or treating chronic diseases is of paramount importance (Raghupathi & Raghupathi, 2018 ▸). Recent advances have shown that many diseases such as cancer, atherosclerosis or neurodegenerative diseases are triggered by inflammation (Furman et al., 2019 ▸). Based on these findings, regulating inflammatory mediators and pathways has been suggested as a treatment strategy (Kany et al., 2019 ▸). Inflammatory stimuli that cause chronic inflammation initiate the production of inflammatory mediators such as inter­leukin-1β (IL-1β), inter­leukin-6 (IL-6) and tumor necrosis factor-α (TNF-α) as a result of the activation of signaling pathways. Receptors activated by inflammatory mediators induce chronic inflammation by various signaling pathways (nuclear factor κ-B (NF-KB), Janus kinase (JAK), signal transducer and activator of transcription (STAT). Inhibiting these pathways may be a promising approach for the treatment of chronic diseases associated with inflammation (Chen et al., 2018 ▸). Nifedipine, the first drug with a 1,4-di­hydro­pyridine (1,4-DHP) ring, was introduced as a therapeutic agent as a result of intensive studies. The success of nifedipine as an anti­hypertensive drug has led to further studies and the discovery of other 1,4-DHP derivatives (De Luca et al., 2019 ▸). Numerous compounds were obtained through modifications with respect to the 1,4-DHP ring. These studies also uncovered the idea of obtaining hexa­hydro­quinoline derivatives by condensation of the 1,4-DHP scaffold with the cyclo­hexane ring system (Bladen et al., 2014 ▸). In recent years, it has been found that 1,4-DHP and quinoline analogs have the potential to inhibit inflammation mediators and pathways, along with various other pharmacological activities (Costa et al., 2010 ▸; Längle et al., 2015 ▸; Kim et al., 2018 ▸; Çetin et al., 2022 ▸). In the current study, tert-butyl 4-[(1,1′-biphen­yl)-4-yl]-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexa­hydro­quinoline-3-carboxyl­ate was obtained by condensation of the 1,4-DHP ring with a substituted cyclo­hexane ring using a modified Hantzsch method. The mol­ecular structure of the compound was confirmed by spectroscopic methods such as IR, 1H NMR, 13C NMR, and its composition by elemental analysis. In addition, single-crystal X-ray analysis was performed to elucidate the crystal structure of the compound. Independent of the current study, biological activity studies of the title compound are ongoing.

Structural commentary

The asymmetric unit of the title compound (Fig. 1 ▸) contains three independent mol­ecules (denoted with suffixes A, B and C). They mainly differ in the twist of the phenyl (C24–C29) and benzene (C18–C23) rings of the 1,1′-biphenyl ring with respect to the plane of the 1,4-di­hydro­pyridine ring (N1/C1–C4/C9). The corresponding dihedral angles amount to 89.26 (16) and 75.83 (19)° in mol­ecule A, 88.34 (17) and 71.7 (2)° in mol­ecule B, and 89.38 (17) and 83.6 (3)° in mol­ecule C. The phenyl and benzene rings of the 1,1′-biphenyl ring make dihedral angles of 39.05 (19)° in A, 46.9 (2)° in B, and 33.5 (2)° in C. Fig. 2 ▸ shows an overlay plot of mol­ecules A, B and C, with an r.m.s. deviation of 0.725 Å. Except for the atoms of the minor part of the disordered mol­ecule C and the phenyl ring of the biphenyl group, the other atoms of mol­ecule C and all atoms of mol­ecules A and B are quite compatible and coincide with each other.
Figure 1

Views from the same direction of the three mol­ecules in the asymmetric unit of the title compound, with displacement ellipsoids for the non-hydrogen atoms drawn at the 30% probability level. (a) Mol­ecule A, (b) mol­ecule B, and (c) mol­ecule C (only the major component of the disorder is shown).

Figure 2

Overlay image of the three independent mol­ecules of the title compound. While the terminal phenyl rings of mol­ecules A and B coincide well, that of mol­ecule C is not in the same plane with them, and is approximately normal to them. Only the major component of the disorder in mol­ecule C is shown.

In all three mol­ecules, the 1,4-di­hydro­pyridine ring adopts a distorted boat conformation with puckering parameters (Cremer & Pople, 1975 ▸) Q T = 0.269 (4) Å, θ = 104.5 (9)° and φ = 357.4 (9)° in A, Q T = 0.257 (4) Å, θ = 73.1 (9)° and φ = 176.0 (9)° in B, and Q T = 0.303 (4) Å, θ = 106.9 (8)° and φ = 356.2 (8)° in C. The cyclo­hexene ring (C4–C9) has an envelope conformation in mol­ecules A and B [the puckering parameters are Q T = 0.430 (4) Å, θ = 49.3 (5)° and φ = 182.3 (7)° in A, and Q T = 0.439 (4) Å, θ = 58.8 (5)° and φ = 179.9 (6)° in B], while the major and minor components of the disordered cyclo­hexene rings in C exhibit a distorted half-chair conformation, with puckering parameters of Q T = 0.451 (9) Å, θ = 44.7 (12)° and φ = 161 (2)° for the major component, and of Q T = 0.44 (2) Å, θ = 50 (3)° and φ = 206 (5)° for the minor component. Bond lengths and angles in the three mol­ecules of the title compound are comparable with those of closely related structures detailed in section 5 (Database survey).

Supra­molecular features

In the crystal, mol­ecules are linked by C—H⋯O and N—H⋯O hydrogen bonds (Table 1 ▸, Fig. 3 ▸), forming layers parallel to (100), defining (6) and C(7) graph-set motifs (Bernstein et al., 1995 ▸). Additional C—H⋯π inter­actions consolidate the layered arrangement (Table 1 ▸; Fig. 4 ▸). Between the layers, van der Waals inter­actions stabilize the packing, as revealed by Hirshfeld surface analysis.
Table 1

Hydrogen-bond geometry (Å, °)

Cg4, Cg8, Cg12 and Cg13 are the centroids of the C18C–C23C, C18A–C23A, C18B–C23B, and C18B–C29B rings, respectively.

D—H⋯A D—HH⋯A D⋯A D—H⋯A
N1C—H1NC⋯O1B i 0.92 (5)1.94 (5)2.843 (4)165 (5)
N1B—H1NB⋯O1C 0.95 (4)1.88 (4)2.811 (4)168 (3)
N1A—H1NA⋯O1A ii 0.93 (5)1.92 (5)2.842 (4)174 (4)
C10A—H10B⋯O1A ii 0.982.603.443 (5)145
C10B—H10F⋯O1C 0.982.473.302 (5)143
C13A—H13A⋯O2A 0.982.452.978 (7)113
C13B—H13D⋯O2B 0.982.473.023 (6)115
C15A—H15A⋯O2A 0.982.412.999 (7)118
C15B—H15D⋯O2B 0.982.412.965 (6)116
C15C—H15G⋯O2C 0.982.493.022 (5)114
C23A—H23A⋯O2A ii 0.952.573.403 (4)147
C23B—H23B⋯O2C 0.952.553.389 (5)147
C23C—H23C⋯O2B i 0.952.603.407 (4)144
C15A—H15B⋯Cg130.982.823.771 (6)165
C27A—H27A⋯Cg4ii 0.952.753.578 (4)146
C27B—H27B⋯Cg80.952.633.493 (5)150
C27C—H27C⋯Cg12iii 0.952.843.632 (7)142

Symmetry codes: (i) ; (ii) ; (iii) .

Figure 3

A view of the inter­molecular N—H⋯O and C—H⋯O inter­actions in the crystal structure of the title compound projected along [100]. Only the major component of the disordered mol­ecule C is shown.

Figure 4

A general view of a part of the mol­ecular packing formed by C—H⋯π inter­actions in the crystal structure of the title compound. Only the major component of the disordered mol­ecule C is shown.

Hirshfeld surface analysis

Crystal Explorer 17.5 (Spackman et al., 2021 ▸) was used to construct Hirshfeld surfaces for the three independent mol­ecules; the disorder of mol­ecule C was included in the calculations. The d norm mappings for mol­ecule A were performed in the range −0.5982 to +2.4710 a.u., for mol­ecule B in the range −0.6131 to +2.5190 a.u., and for mol­ecule C in the range −0.6097 to +2.4293 a.u.. On the d norm surfaces, bright-red spots show the locations of N—H⋯O and C—H⋯O inter­actions (Fig. 5 ▸ a for mol­ecule A, Fig. 5 ▸ b for mol­ecule B, and Fig. 5 ▸ c for mol­ecule C).
Figure 5

(a) View of the three-dimensional Hirshfeld surface for mol­ecule A; (b) view of the three-dimensional Hirshfeld surface for mol­ecule B; (c) view of the three-dimensional Hirshfeld surface for mol­ecule C. Some inter­molecular N—H⋯O and C—H⋯O inter­actions are shown as dashed lines.

Fingerprint plots (Fig. 6 ▸) reveal that H⋯H inter­actions make the largest contributions (69.6% for mol­ecule A, 69.9% for mol­ecule B, and 70.1% for mol­ecule C) to the overall surface (Table 2 ▸). C⋯H/H⋯C (20.3% for A, 20.6% for B, and 20.3% for C) contacts are also significant. Table 3 ▸ lists the contributions of additional, less notable inter­actions. As seen in Table 3 ▸, the relevant contacts around mol­ecules A, B, and C are quite similar.
Figure 6

The two-dimensional fingerprint plots for mol­ecules A, B and C showing (a) all inter­actions, and delineated into (b) H⋯H, (c) C⋯H/H⋯C and (d) O⋯H/H⋯O inter­actions. The d i and d e values are the closest inter­nal and external distances (in Å) from given points on the Hirshfeld surface.

Table 2

Summary of short inter­atomic contacts (Å) in the title compound

ContactDistanceSymmetry operation
O1C⋯H1NB 1.88 x, y, z
H1NC⋯O1B 1.94 x, y, −1 + z
H10I⋯H14B 2.401 − x, 1 − y, −  + z
C8C⋯H16K 3.071 − x, −y, −  + z
H10G⋯H13H 2.431 − x, 1 − y, −  + z
C19C⋯H27A 2.86  − x, y, −  + z
H26C⋯C20B 2.90  − x, y, −  + z
H17K⋯H10E 2.071 − x, −y, −  + z
H16G⋯H17A 2.52  − x, −1 + y, −  + z
H20C⋯H28C 2.56  − x, y, −  + z
O1A⋯H1NA 1.92  − x, y, −  + z
H7AA⋯H15E 2.49 x, 1 + y, z
H10B⋯H17D 2.511 − x, 1 − y,  + z
H16A⋯H17F 2.47−  + x, 1 − y, z
C19A⋯H27B 2.89 x, y, z
H16B⋯C10B 2.97  − x, y, −  + z
H28A⋯H20B 2.42  − x, y, −  + z
Table 3

Percentage contributions of inter­atomic contacts to the Hirshfeld surfaces for the mol­ecules A, B and C of the title compound

Contact% for A % for B % for C
H⋯H69.669.970.1
C⋯H/H⋯C20.320.620.3
O⋯H/H⋯O8.68.68.4
N⋯H/H⋯N1.10.80.9
C⋯C0.50.10.4

Database survey

A search of the Cambridge Structural Database (CSD, Version 5.42, update of September 2021; Groom et al., 2016 ▸) for similar structures with the 1,4,5,6,7,8-hexa­hydro­quinoline unit revealed seven closely related entries: ethyl 4-(4-bromo­phen­yl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexa­hydro­quinoline-3-carboxyl­ate [CSD refcode LOQCAX (I); Steiger et al., 2014 ▸], ethyl 4-(3-hy­droxy­phen­yl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexa­hydro­quinoline-3-carboxyl­ate [PUGCIE (II); Mookiah et al., 2009 ▸], (RR,SS)-methyl 4-(2,4-chloro­phen­yl)-2,7-dimethyl-5-oxo-1,4,5,6,7,8-hexa­hydro­quinoline-3-carb­oxy­l­ate (RS,SR)-methyl 4-(2,4-chloro­phen­yl)-2,7-dimethyl-5-oxo-1,4,5,6,7,8-hexa­hydro­quinoline-3-carboxyl­ate [UCOLOO (III); Linden et al., 2006 ▸], ethyl 2,7,7-trimethyl-4-(1-methyl-1H-indol-3-yl)-5-oxo-1,4,5,6,7,8-hexa­hydro­quinoline-3-carb­oxyl­ate [NEQMON (IV); Öztürk Yildirim et al., 2013 ▸], (+/−)-methyl 4-(2,3-di­fluoro­phen­yl)-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexa­hydro­quinoline-3-carboxyl­ate [DAYJET (V); Linden et al., 2005 ▸], benzyl 4-(3-chloro-2-fluoro­phen­yl)-2-methyl-5-oxo-4,5,6,7-tetra­hydro-1H-cyclo­penta­[b]pyridine-3-carboxyl­ate [IMEJOA (VI); Linden et al., 2011 ▸], and ethyl 4-(5-bromo-1H-indol-3-yl)-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexa­hydro­quinoline-3-carboxyl­ate [PECPUK (VII); Gündüz et al., 2012 ▸]. In (I), hydrogen bonds are formed between the N—H group of one mol­ecule and the carbonyl O atom in the cyclo­hexa­none ring of an adjacent mol­ecule. These hydrogen bonds link the mol­ecules into extended chains running along [001]. In the crystal of (II), mol­ecules are linked by N—H⋯O and O—H⋯O hydrogen bonds into layers parallel to (101). The network includes (30) and (34) graph-set motifs. In (III), an inter­molecular N—H⋯O hydrogen bond between the amine group and the carbonyl O atom of the cyclo­hexenone ring of a neighboring mol­ecule links the mol­ecules into extended chains parallel to [101]. These inter­actions can be described by graph-set motif C(6). In the crystal of (IV), N—H⋯O hydrogen bonds connect the mol­ecules into C(6) chains parallel to [010], and pairs of weak C—H⋯O hydrogen bonds link inversion-related chains into a ladder motif through (18) rings. A weak intra­molecular C—H⋯O hydrogen bond is also observed. In (V), the crystal structure exhibits an inter­molecular N—H⋯O hydrogen-bonding inter­action involving the carbonyl O atom of the oxo­cyclo­hexene ring, whereby the mol­ecules are linked into C(6) chains parallel to [100]. In (VI), the frequently observed inter­molecular N—H⋯O hydrogen bond between the amine group and the carbonyl O atom of the oxo­cyclo­pentene ring of a neighboring mol­ecule links the mol­ecules into extended C(6) chains parallel to [010]; there are no other significant inter­molecular inter­actions. In the crystal of (VII), mol­ecules are linked by pairs of N—H⋯O hydrogen bonds, forming dimers with (6) ring motifs. These dimers are connected by N—H⋯O hydrogen bonds, generating chains along [110]. A C—H⋯O contact occurs between the independent mol­ecules.

Synthesis and crystallization

The title compound was synthesized via a Hantzsch reaction. 4,4-Di­methyl­cyclo­hexane-1,3-dione (1 mmol), [1,1′-biphen­yl]-4-carbaldehyde (1 mmol), tert-butyl aceto­acetate (1 mmol), and ammonium acetate (5 mmol) were refluxed for 8 h in absolute methanol (10 ml). The reaction mixture was monitored by TLC, and after completion of the reaction was cooled to room temperature. The obtained precipitate was filtered and recrystallized from ethanol for further purification. The synthetic route is shown in Fig. 7 ▸.
Figure 7

Schematic synthetic route for the title compound.

Yellowish solid, m.p. 520-522 K; yield: 41%. IR (ν, cm−1) 3284 (N—H, stretching), 3067 (C—H stretching, aromatic), 2966 (C—H stretching, aliphatic) 1671 (C=O stretching, ester), 1597 (C=O stretching, ketone). 1H NMR (DMSO-d 6) δ: 0.88 (3H; s; 6-CH3), 0.97 (3H; s; 6-CH3), 1.32 [9H, s, C(CH3)3], 1.70–1.71 (2H; m; quinoline H7), 2.23 (3H; s; 2-CH3), 2.47–2.50 (2H; m; quinoline H8), 4.82 (1H; s; quinoline H4), 7.19–7.21 (2H, m, Ar-H), 7.27–7.31 (H, m, Ar-H), 7.38–7.48 (4H, m, Ar-H), 7.57–7.59 (2H, m, Ar-H), 8.98 (1H, s; NH). 13C NMR (DMSO-d 6) δ: 18.2, 22.9, 24.1, 25.1, 27.9, 34.1, 36.0, 40.0, 78.7, 104.6, 108.8, 126.0, 126.3, 127.0, 127.9, 128.7, 137.3, 140.1, 143.8, 147.1, 149.8, 166.4, 199.3. Analysis calculated for C29H33NO3: C 78.52, H 7.5, N 3.16. Found: C 78.30, H 7.602, N 3.19.

Refinement details

Crystal data, data collection and structure refinement details are summarized in Table 4 ▸. All C-bound H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.95 Å for aryl-H atoms, C—H = 0.99 Å for methyl­ene groups, C—H = 1.00 Å for methine groups and C—H = 0.98 Å for methyl groups, with U iso(H) = 1.5U eq(C) for methyl groups and U iso(H) = 1.2U eq(C) for other hydrogen atoms. The H atoms of the NH groups were found in a difference-Fourier map and refined freely (see Table 1 ▸).
Table 4

Experimental details

Crystal data
Chemical formulaC29H33NO3
M r 443.56
Crystal system, space groupOrthorhombic, P c a21
Temperature (K)100
a, b, c (Å)33.2247 (14), 19.0904 (7), 12.0370 (3)
V (Å3)7634.7 (5)
Z 12
Radiation typeMo Kα
μ (mm−1)0.07
Crystal size (mm)0.29 × 0.17 × 0.04
 
Data collection
DiffractometerSuperNova, Dual, Cu at zero, Atlas
Absorption correctionGaussian (CrysAlis PRO; Rigaku OD, 2015 ▸)
T min, T max 0.984, 0.997
No. of measured, independent and observed [I > 2σ(I)] reflections69430, 26062, 13388
R int 0.091
(sin θ/λ)max (Å−1)0.815
 
Refinement
R[F 2 > 2σ(F 2)], wR(F 2), S 0.077, 0.212, 1.02
No. of reflections26062
No. of parameters943
No. of restraints13
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.58, −0.37

Computer programs: CrysAlis PRO (Rigaku OD, 2015 ▸), SHELXT (Sheldrick, 2015a ▸), SHELXL (Sheldrick, 2015b ▸), ORTEP-3 for Windows (Farrugia, 2012 ▸), and PLATON (Spek, 2020 ▸).

In mol­ecule C, except the fused carbon atoms (C4C and C9C) and the carbonyl oxygen atom (O1C) of the 6,6-di­methyl­cyclo­hex-2-en-1-one group (C4 –C5C/C5F–C6C/C6F–C7C/C7F–C8C/C8F–C9 –O1 –C16C/C16F–C17C/C17F), the other C atoms are disordered over two sets of sites with a refined occupancy ratio of 0.716 (4):0.284 (4). For the disordered components, the EADP instruction was used in the final cycles of the refinement. Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989022007022/wm5652sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989022007022/wm5652Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S2056989022007022/wm5652Isup3.cml CCDC reference: 2185278 Additional supporting information: crystallographic information; 3D view; checkCIF report
C29H33NO3Dx = 1.158 Mg m−3
Mr = 443.56Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21Cell parameters from 9135 reflections
a = 33.2247 (14) Åθ = 3.7–29.8°
b = 19.0904 (7) ŵ = 0.07 mm−1
c = 12.0370 (3) ÅT = 100 K
V = 7634.7 (5) Å3Plate, colorless
Z = 120.28 × 0.17 × 0.04 mm
F(000) = 2856
SuperNova, Dual, Cu at zero, Atlas diffractometer26062 independent reflections
Radiation source: micro-focus sealed X-ray tube13388 reflections with I > 2σ(I)
Detector resolution: 10.6501 pixels mm-1Rint = 0.091
ω scansθmax = 35.4°, θmin = 3.4°
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2015\bbr021)h = −52→45
Tmin = 0.984, Tmax = 0.997k = −30→18
69430 measured reflectionsl = −12→19
Refinement on F213 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.077H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.212w = 1/[σ2(Fo2) + (0.0858P)2 + 0.3289P] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
26062 reflectionsΔρmax = 0.58 e Å−3
943 parametersΔρmin = −0.37 e Å−3
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.
xyzUiso*/UeqOcc. (<1)
O1C0.46360 (9)0.08706 (13)0.3497 (2)0.0319 (6)
O2C0.45841 (11)0.33966 (14)0.4075 (2)0.0401 (8)
O3C0.48150 (10)0.41061 (13)0.2723 (2)0.0333 (7)
N1C0.48126 (9)0.24320 (15)0.0522 (2)0.0210 (6)
H1NC0.4898 (17)0.253 (3)−0.019 (4)0.054 (15)*
C1C0.47707 (11)0.30241 (18)0.1187 (3)0.0217 (7)
C2C0.46516 (11)0.29472 (18)0.2253 (3)0.0215 (7)
C3C0.44911 (11)0.22483 (17)0.2661 (3)0.0195 (6)
H3CA0.4571160.2193900.3457660.023*
C4C0.46876 (12)0.16588 (18)0.2003 (3)0.0223 (7)
C9C0.48166 (11)0.17716 (18)0.0953 (3)0.0216 (7)
C10C0.48761 (13)0.36843 (19)0.0585 (3)0.0280 (8)
H10G0.4697790.4062700.0830770.042*
H10H0.4843580.361273−0.0216310.042*
H10I0.5156060.3810250.0745730.042*
C11C0.46732 (13)0.34996 (18)0.3106 (3)0.0252 (8)
C12C0.48964 (15)0.4703 (2)0.3458 (3)0.0363 (10)
C13C0.52017 (17)0.4500 (3)0.4339 (4)0.0531 (14)
H13G0.5064160.4261220.4951790.080*
H13H0.5335420.4921490.4619510.080*
H13I0.5402530.4184570.4013440.080*
C14C0.5076 (2)0.5231 (2)0.2654 (4)0.0633 (17)
H14G0.4891800.5299800.2027940.095*
H14H0.5334720.5056060.2379400.095*
H14I0.5117330.5678450.3037600.095*
C15C0.45081 (16)0.4972 (2)0.3945 (4)0.0455 (12)
H15G0.4405970.4634920.4490290.068*
H15H0.4309400.5032720.3350770.068*
H15I0.4556340.5423140.4309750.068*
C5C0.4736 (4)0.0987 (5)0.2485 (11)0.0182 (16)0.716 (4)
C6C0.4829 (2)0.0353 (4)0.1732 (5)0.0231 (13)0.716 (4)
C7C0.51262 (18)0.0589 (3)0.0831 (4)0.0254 (10)0.716 (4)
H7CA0.5384590.0717200.1186450.030*0.716 (4)
H7CB0.5178370.0191370.0322860.030*0.716 (4)
C8C0.4976 (7)0.1206 (6)0.0158 (11)0.0219 (16)0.716 (4)
H8CA0.4758840.105316−0.0349220.026*0.716 (4)
H8CB0.5198480.139966−0.0296170.026*0.716 (4)
C16C0.44347 (19)0.0096 (3)0.1220 (5)0.0347 (12)0.716 (4)
H16G0.425520−0.0069790.1810010.052*0.716 (4)
H16H0.449072−0.0287830.0703020.052*0.716 (4)
H16I0.4305240.0482340.0819180.052*0.716 (4)
C17C0.5016 (2)−0.0234 (3)0.2432 (5)0.0392 (14)0.716 (4)
H17G0.483035−0.0363710.3030370.059*0.716 (4)
H17H0.527040−0.0071180.2752770.059*0.716 (4)
H17I0.506661−0.0642980.1959790.059*0.716 (4)
C5F0.4673 (10)0.0923 (15)0.258 (3)0.0182 (16)0.284 (4)
C6F0.4902 (6)0.0350 (11)0.1928 (15)0.0231 (13)0.284 (4)
C7F0.4842 (5)0.0458 (6)0.0679 (10)0.0254 (10)0.284 (4)
H7FA0.5009500.0117190.0267450.030*0.284 (4)
H7FB0.4556770.0369070.0487340.030*0.284 (4)
C8F0.495 (2)0.1197 (14)0.032 (3)0.0219 (16)0.284 (4)
H8FA0.5252390.1223020.0301510.026*0.284 (4)
H8FB0.4858320.126208−0.0447620.026*0.284 (4)
C16F0.4713 (5)−0.0345 (7)0.2282 (12)0.0347 (12)0.284 (4)
H16J0.442582−0.0342220.2101250.052*0.284 (4)
H16K0.474775−0.0406810.3084850.052*0.284 (4)
H16L0.484577−0.0730230.1888480.052*0.284 (4)
C17F0.5351 (5)0.0358 (8)0.2264 (11)0.0392 (14)0.284 (4)
H17J0.5457850.0833780.2182020.059*0.284 (4)
H17K0.5501990.0037520.1784580.059*0.284 (4)
H17L0.5377490.0208800.3039860.059*0.284 (4)
C18C0.40349 (11)0.22258 (16)0.2602 (3)0.0205 (7)
C19C0.37983 (13)0.23298 (19)0.3550 (3)0.0287 (8)
H19C0.3924330.2383120.4252950.034*
C20C0.33815 (13)0.2356 (2)0.3474 (3)0.0334 (9)
H20C0.3226490.2415510.4130310.040*
C21C0.31872 (13)0.22971 (19)0.2458 (3)0.0314 (8)
C22C0.34244 (13)0.2192 (2)0.1517 (3)0.0307 (8)
H22C0.3297900.2148370.0812960.037*
C23C0.38374 (12)0.21487 (19)0.1584 (3)0.0255 (7)
H23C0.3990050.2065660.0929690.031*
C24C0.27417 (14)0.2351 (2)0.2377 (4)0.0413 (10)
C25C0.25248 (19)0.2794 (3)0.3068 (6)0.0682 (17)
H25C0.2663390.3057370.3617700.082*
C26C0.2112 (2)0.2862 (4)0.2975 (7)0.082 (2)
H26C0.1970010.3162920.3466520.098*
C27C0.19067 (19)0.2494 (4)0.2174 (6)0.075 (2)
H27C0.1623810.2550190.2101790.090*
C28C0.21126 (18)0.2037 (3)0.1465 (6)0.0662 (17)
H28C0.1970130.1778390.0916650.079*
C29C0.25298 (16)0.1963 (3)0.1569 (5)0.0510 (12)
H29C0.2671070.1651410.1093220.061*
C1B0.42485 (12)0.13678 (18)0.6165 (3)0.0226 (7)
O1B0.52165 (8)0.27146 (15)0.8489 (2)0.0301 (6)
O2B0.39953 (9)0.13889 (15)0.9060 (2)0.0337 (7)
O3B0.36660 (9)0.08654 (15)0.7645 (2)0.0352 (7)
N1B0.45666 (10)0.16087 (16)0.5509 (2)0.0238 (6)
H1NB0.4580 (11)0.1419 (18)0.478 (3)0.015 (9)*
C2B0.42144 (11)0.15947 (18)0.7226 (3)0.0215 (7)
C3B0.44784 (11)0.21896 (17)0.7645 (3)0.0192 (6)
H3BA0.4551380.2085520.8434200.023*
C4B0.48650 (11)0.22308 (17)0.6980 (3)0.0202 (7)
C5B0.52170 (11)0.25356 (17)0.7503 (3)0.0214 (7)
C6B0.56081 (13)0.2624 (2)0.6833 (3)0.0283 (8)
C7B0.55222 (14)0.2632 (2)0.5602 (3)0.0353 (9)
H7BA0.5780690.2608240.5194840.042*
H7BB0.5391920.3082430.5409510.042*
C8B0.52497 (12)0.2027 (2)0.5206 (3)0.0274 (8)
H8BA0.5165170.2111700.4429310.033*
H8BB0.5402040.1581210.5228270.033*
C9B0.48827 (12)0.19693 (18)0.5940 (3)0.0217 (7)
C10B0.39848 (14)0.0853 (2)0.5569 (3)0.0327 (9)
H10D0.3702420.0991900.5651370.049*
H10E0.4023630.0385140.5886960.049*
H10F0.4055930.0844980.4778900.049*
C11B0.39505 (12)0.12824 (19)0.8071 (3)0.0249 (7)
C12B0.34032 (15)0.0438 (2)0.8350 (4)0.0408 (11)
C13B0.36627 (19)−0.0084 (3)0.8969 (5)0.0636 (16)
H13D0.3825590.0162530.9523720.095*
H13E0.384013−0.0325060.8442980.095*
H13F0.349019−0.0428100.9341820.095*
C14B0.31430 (18)0.0074 (3)0.7477 (4)0.0605 (16)
H14D0.3000550.0427090.7036070.091*
H14E0.294700−0.0230520.7847230.091*
H14F0.331456−0.0207870.6988740.091*
C15B0.31514 (17)0.0884 (3)0.9105 (4)0.0538 (14)
H15D0.3324460.1106150.9662850.081*
H15E0.2950270.0591340.9477830.081*
H15F0.3015160.1246680.8668330.081*
C16B0.58283 (17)0.3280 (3)0.7172 (5)0.0588 (15)
H16D0.5673360.3691130.6938580.088*
H16E0.6093640.3288810.6817090.088*
H16F0.5861010.3286340.7981260.088*
C17B0.58741 (17)0.1989 (3)0.7168 (4)0.0548 (14)
H17D0.6141250.2038790.6832440.082*
H17E0.5748620.1555390.6905420.082*
H17F0.5900320.1973480.7979010.082*
C18B0.42474 (11)0.28796 (17)0.7628 (3)0.0201 (6)
C19B0.40710 (11)0.31303 (19)0.8600 (3)0.0236 (7)
H19B0.4110610.2885120.9277880.028*
C20B0.38374 (12)0.37360 (19)0.8589 (3)0.0278 (8)
H20B0.3720960.3900380.9261440.033*
C21B0.37724 (12)0.41026 (19)0.7609 (3)0.0271 (8)
C22B0.39484 (12)0.38486 (19)0.6634 (3)0.0270 (8)
H22B0.3906340.4088710.5952680.032*
C23B0.41843 (12)0.32481 (18)0.6654 (3)0.0243 (7)
H23B0.4304700.3087220.5984700.029*
C24B0.35100 (13)0.4735 (2)0.7599 (3)0.0306 (8)
C25B0.32067 (16)0.4813 (3)0.6810 (4)0.0496 (12)
H25B0.3174200.4466610.6249960.059*
C26B0.29521 (18)0.5386 (3)0.6827 (5)0.0590 (15)
H26B0.2748370.5433580.6278130.071*
C27B0.29953 (17)0.5892 (2)0.7652 (4)0.0494 (12)
H27B0.2817950.6282570.7674200.059*
C28B0.32936 (16)0.5828 (2)0.8431 (4)0.0449 (11)
H28B0.3325750.6174970.8990390.054*
C29B0.35499 (15)0.5249 (2)0.8398 (4)0.0392 (10)
H29B0.3756870.5207360.8938770.047*
O1A0.19045 (8)0.90494 (14)0.6522 (2)0.0291 (6)
O2A0.31575 (10)0.77814 (17)0.5886 (2)0.0413 (8)
O3A0.35749 (9)0.75149 (15)0.7299 (2)0.0327 (6)
N1A0.27887 (10)0.85463 (16)0.9468 (2)0.0225 (6)
H1NA0.2869 (14)0.872 (2)1.015 (4)0.034 (12)*
C1A0.30583 (12)0.81797 (19)0.8791 (3)0.0234 (7)
C2A0.29537 (11)0.80338 (18)0.7730 (3)0.0217 (7)
C3A0.25278 (11)0.81758 (17)0.7316 (3)0.0216 (7)
H3AA0.2545550.8336560.6527170.026*
C4A0.23328 (11)0.87495 (17)0.7985 (3)0.0201 (7)
C5A0.20096 (11)0.91507 (18)0.7502 (3)0.0225 (7)
C6A0.17859 (12)0.96972 (19)0.8190 (3)0.0248 (7)
C7A0.20552 (13)0.9979 (2)0.9126 (3)0.0334 (9)
H7AA0.2266181.0281710.8798710.040*
H7AB0.1890381.0272780.9628940.040*
C8A0.22563 (12)0.9401 (2)0.9804 (3)0.0258 (8)
H8AA0.2456700.9609791.0315080.031*
H8AB0.2051420.9155491.0256650.031*
C9A0.24611 (12)0.88866 (17)0.9046 (3)0.0213 (7)
C10A0.34394 (12)0.8005 (2)0.9392 (3)0.0280 (8)
H10A0.3488280.7499830.9348350.042*
H10B0.3415180.8145131.0172660.042*
H10C0.3664550.8256800.9049070.042*
C11A0.32364 (12)0.77620 (19)0.6876 (3)0.0244 (7)
C12A0.39117 (12)0.7288 (2)0.6574 (3)0.0343 (9)
C13A0.4052 (2)0.7882 (3)0.5884 (6)0.082 (2)
H13A0.3854390.7975940.5298050.123*
H13B0.4311600.7763950.5546940.123*
H13C0.4082380.8299310.6350930.123*
C14A0.42246 (17)0.7077 (5)0.7437 (5)0.086 (2)
H14A0.4345320.7498340.7761520.128*
H14B0.4434690.6795050.7081350.128*
H14C0.4094930.6801560.8023710.128*
C15A0.37950 (17)0.6669 (3)0.5897 (5)0.0580 (15)
H15A0.3575150.6797470.5394310.087*
H15B0.3705860.6290610.6389920.087*
H15C0.4026980.6510170.5462180.087*
C16A0.14186 (14)0.9325 (2)0.8690 (4)0.0414 (11)
H16A0.1236190.9181080.8092040.062*
H16B0.1277710.9644960.9193510.062*
H16C0.1507500.8910410.9103240.062*
C17A0.16505 (16)1.0306 (2)0.7470 (4)0.0450 (11)
H17A0.1494661.0128120.6839090.068*
H17B0.1886881.0559730.7195450.068*
H17C0.1482571.0623660.7910920.068*
C18A0.22898 (11)0.74917 (18)0.7339 (3)0.0211 (7)
C19A0.22517 (12)0.70862 (19)0.6374 (3)0.0255 (8)
H19A0.2356320.7255140.5690050.031*
C20A0.20609 (13)0.64357 (19)0.6413 (3)0.0281 (8)
H20A0.2033710.6170120.5750070.034*
C21A0.19106 (12)0.61693 (18)0.7399 (3)0.0262 (7)
C22A0.19480 (12)0.6574 (2)0.8352 (3)0.0296 (8)
H22A0.1845860.6401520.9036340.035*
C23A0.21326 (12)0.7228 (2)0.8321 (3)0.0262 (8)
H23A0.2151200.7498050.8982610.031*
C24A0.17181 (13)0.5460 (2)0.7452 (3)0.0318 (9)
C25A0.17811 (16)0.5014 (2)0.8345 (4)0.0472 (12)
H25A0.1943310.5164140.8950400.057*
C26A0.16085 (19)0.4349 (3)0.8364 (5)0.0583 (15)
H26A0.1657980.4045380.8973850.070*
C27A0.13681 (17)0.4132 (2)0.7507 (5)0.0480 (12)
H27A0.1251110.3677710.7521730.058*
C28A0.12964 (17)0.4572 (2)0.6627 (4)0.0490 (13)
H28A0.1125010.4423350.6040530.059*
C29A0.14713 (15)0.5229 (2)0.6584 (4)0.0415 (11)
H29A0.1423600.5524670.5963350.050*
U11U22U33U12U13U23
O1C0.051 (2)0.0247 (13)0.0196 (12)0.0041 (12)0.0034 (12)0.0022 (10)
O2C0.069 (2)0.0285 (14)0.0226 (13)−0.0081 (15)0.0078 (13)−0.0045 (11)
O3C0.052 (2)0.0240 (13)0.0240 (13)−0.0068 (12)0.0055 (12)−0.0046 (10)
N1C0.0224 (16)0.0256 (14)0.0149 (12)−0.0024 (12)0.0018 (11)−0.0009 (11)
C1C0.0212 (19)0.0229 (16)0.0210 (15)0.0036 (14)−0.0036 (12)0.0010 (12)
C2C0.0246 (19)0.0239 (16)0.0161 (14)0.0031 (14)−0.0019 (12)−0.0019 (12)
C3C0.0234 (18)0.0215 (15)0.0136 (13)0.0037 (13)−0.0006 (12)−0.0008 (12)
C4C0.023 (2)0.0247 (16)0.0187 (15)0.0021 (14)−0.0022 (12)−0.0013 (12)
C9C0.0209 (19)0.0270 (17)0.0168 (14)0.0012 (14)−0.0027 (12)−0.0021 (12)
C10C0.035 (2)0.0270 (17)0.0223 (16)−0.0047 (16)0.0009 (15)0.0011 (14)
C11C0.034 (2)0.0207 (16)0.0205 (16)0.0028 (15)0.0010 (14)−0.0016 (12)
C12C0.053 (3)0.0259 (19)0.0297 (19)−0.0027 (19)0.0014 (19)−0.0097 (16)
C13C0.053 (4)0.045 (3)0.061 (3)0.006 (2)−0.017 (3)−0.021 (2)
C14C0.110 (5)0.035 (2)0.045 (3)−0.030 (3)0.015 (3)−0.012 (2)
C15C0.051 (3)0.034 (2)0.052 (3)0.000 (2)−0.004 (2)−0.017 (2)
C5C0.017 (5)0.021 (3)0.017 (3)−0.002 (2)0.005 (2)0.001 (2)
C6C0.028 (4)0.0228 (17)0.019 (3)0.004 (2)−0.002 (2)−0.002 (2)
C7C0.029 (3)0.022 (2)0.026 (2)0.003 (2)0.001 (2)−0.0031 (17)
C8C0.028 (4)0.0290 (18)0.009 (5)0.0022 (17)0.005 (4)−0.0020 (19)
C16C0.042 (4)0.030 (3)0.032 (3)0.001 (2)0.002 (2)−0.009 (2)
C17C0.058 (4)0.033 (3)0.027 (3)0.020 (3)−0.002 (2)−0.003 (2)
C5F0.017 (5)0.021 (3)0.017 (3)−0.002 (2)0.005 (2)0.001 (2)
C6F0.028 (4)0.0228 (17)0.019 (3)0.004 (2)−0.002 (2)−0.002 (2)
C7F0.029 (3)0.022 (2)0.026 (2)0.003 (2)0.001 (2)−0.0031 (17)
C8F0.028 (4)0.0290 (18)0.009 (5)0.0022 (17)0.005 (4)−0.0020 (19)
C16F0.042 (4)0.030 (3)0.032 (3)0.001 (2)0.002 (2)−0.009 (2)
C17F0.058 (4)0.033 (3)0.027 (3)0.020 (3)−0.002 (2)−0.003 (2)
C18C0.0265 (19)0.0162 (13)0.0189 (14)0.0028 (13)0.0046 (13)0.0023 (12)
C19C0.033 (2)0.0301 (19)0.0229 (17)0.0065 (17)0.0063 (15)0.0023 (14)
C20C0.031 (2)0.037 (2)0.032 (2)0.0077 (18)0.0126 (17)0.0007 (17)
C21C0.026 (2)0.0271 (18)0.041 (2)0.0035 (16)0.0062 (17)0.0057 (16)
C22C0.024 (2)0.035 (2)0.032 (2)−0.0013 (17)−0.0020 (16)0.0040 (16)
C23C0.025 (2)0.0289 (18)0.0231 (16)−0.0002 (15)0.0003 (14)0.0007 (14)
C24C0.026 (2)0.044 (2)0.054 (3)0.0030 (19)0.0069 (19)0.012 (2)
C25C0.034 (3)0.071 (4)0.099 (5)0.014 (3)0.014 (3)−0.007 (3)
C26C0.035 (4)0.084 (5)0.126 (6)0.016 (3)0.021 (4)0.003 (4)
C27C0.024 (3)0.084 (4)0.116 (6)0.011 (3)0.006 (3)0.031 (4)
C28C0.035 (3)0.082 (4)0.082 (4)−0.003 (3)−0.005 (3)0.031 (3)
C29C0.031 (3)0.059 (3)0.063 (3)−0.003 (2)−0.001 (2)0.017 (3)
C1B0.026 (2)0.0222 (16)0.0201 (15)0.0013 (14)−0.0041 (13)0.0027 (12)
O1B0.0243 (15)0.0471 (16)0.0189 (12)−0.0089 (12)0.0020 (10)−0.0034 (11)
O2B0.0331 (18)0.0481 (17)0.0200 (12)−0.0136 (13)0.0004 (11)−0.0024 (11)
O3B0.0350 (18)0.0450 (16)0.0257 (13)−0.0183 (13)0.0066 (12)−0.0055 (12)
N1B0.0297 (18)0.0278 (15)0.0139 (12)0.0022 (13)−0.0001 (11)−0.0024 (11)
C2B0.0207 (18)0.0262 (16)0.0176 (15)0.0014 (14)−0.0003 (12)0.0002 (12)
C3B0.0215 (17)0.0222 (15)0.0140 (13)−0.0005 (13)−0.0007 (12)0.0008 (12)
C4B0.0200 (18)0.0220 (16)0.0187 (15)0.0037 (13)0.0012 (12)0.0027 (12)
C5B0.0205 (18)0.0240 (16)0.0198 (16)0.0010 (13)0.0025 (12)0.0043 (12)
C6B0.030 (2)0.0313 (19)0.0232 (17)−0.0034 (17)0.0063 (14)−0.0010 (14)
C7B0.032 (2)0.042 (2)0.031 (2)−0.0033 (19)0.0056 (17)0.0034 (17)
C8B0.025 (2)0.038 (2)0.0189 (15)0.0042 (17)0.0052 (13)−0.0001 (14)
C9B0.026 (2)0.0226 (16)0.0160 (14)0.0043 (14)0.0009 (13)0.0024 (12)
C10B0.035 (2)0.036 (2)0.0268 (18)−0.0076 (18)−0.0038 (16)−0.0062 (16)
C11B0.022 (2)0.0288 (18)0.0237 (16)−0.0002 (15)0.0001 (13)−0.0028 (13)
C12B0.044 (3)0.043 (2)0.035 (2)−0.025 (2)0.0019 (19)0.0035 (18)
C13B0.065 (4)0.048 (3)0.078 (4)−0.016 (3)0.009 (3)0.020 (3)
C14B0.059 (4)0.073 (3)0.050 (3)−0.044 (3)0.014 (2)−0.018 (3)
C15B0.044 (3)0.072 (3)0.046 (3)−0.023 (3)0.020 (2)−0.005 (2)
C16B0.038 (3)0.082 (4)0.056 (3)−0.022 (3)0.014 (2)−0.004 (3)
C17B0.045 (3)0.083 (4)0.036 (3)0.020 (3)0.002 (2)0.009 (2)
C18B0.0179 (17)0.0232 (15)0.0190 (14)0.0008 (13)−0.0030 (12)−0.0010 (12)
C19B0.023 (2)0.0314 (18)0.0169 (15)0.0025 (15)−0.0006 (12)−0.0004 (13)
C20B0.026 (2)0.0313 (19)0.0254 (17)0.0046 (16)0.0028 (14)−0.0054 (14)
C21B0.0221 (19)0.0273 (18)0.0318 (18)0.0031 (14)0.0003 (15)0.0012 (15)
C22B0.027 (2)0.0312 (19)0.0225 (16)0.0056 (16)−0.0022 (14)0.0012 (14)
C23B0.026 (2)0.0274 (17)0.0193 (16)0.0041 (15)0.0021 (13)−0.0009 (13)
C24B0.029 (2)0.0309 (19)0.0322 (19)0.0077 (16)0.0048 (16)0.0023 (16)
C25B0.040 (3)0.048 (3)0.061 (3)0.011 (2)−0.007 (2)−0.001 (2)
C26B0.040 (3)0.056 (3)0.081 (4)0.021 (3)−0.009 (3)0.001 (3)
C27B0.043 (3)0.043 (2)0.063 (3)0.017 (2)0.008 (2)0.001 (2)
C28B0.052 (3)0.035 (2)0.047 (3)0.008 (2)0.015 (2)−0.0005 (19)
C29B0.040 (3)0.035 (2)0.043 (2)0.0089 (19)0.009 (2)0.0032 (18)
O1A0.0263 (15)0.0419 (15)0.0191 (12)0.0097 (12)−0.0028 (10)−0.0048 (11)
O2A0.0344 (18)0.071 (2)0.0184 (13)0.0237 (16)0.0006 (11)−0.0042 (13)
O3A0.0216 (15)0.0526 (17)0.0237 (13)0.0112 (13)0.0013 (10)−0.0044 (12)
N1A0.0264 (17)0.0281 (15)0.0130 (12)−0.0003 (13)−0.0024 (11)−0.0015 (11)
C1A0.024 (2)0.0279 (17)0.0187 (15)−0.0025 (15)−0.0002 (12)0.0023 (12)
C2A0.0217 (19)0.0252 (16)0.0181 (15)0.0023 (14)0.0000 (12)−0.0027 (13)
C3A0.0218 (18)0.0272 (17)0.0158 (13)0.0028 (14)0.0011 (12)−0.0007 (12)
C4A0.0225 (19)0.0212 (15)0.0167 (14)0.0018 (14)0.0018 (12)−0.0013 (12)
C5A0.0261 (19)0.0263 (16)0.0150 (15)0.0004 (14)0.0015 (13)−0.0008 (12)
C6A0.025 (2)0.0272 (17)0.0223 (16)0.0063 (15)0.0007 (13)−0.0014 (13)
C7A0.031 (2)0.037 (2)0.0323 (19)0.0028 (18)0.0019 (16)−0.0064 (16)
C8A0.026 (2)0.0319 (19)0.0198 (15)0.0006 (16)0.0022 (13)−0.0072 (14)
C9A0.0247 (19)0.0229 (15)0.0162 (14)−0.0021 (14)0.0027 (12)−0.0017 (12)
C10A0.023 (2)0.040 (2)0.0214 (16)0.0038 (16)−0.0018 (14)−0.0011 (15)
C11A0.0205 (19)0.0312 (18)0.0217 (16)0.0027 (15)−0.0003 (13)−0.0020 (13)
C12A0.0164 (19)0.058 (3)0.0289 (19)0.0097 (18)0.0023 (14)−0.0045 (18)
C13A0.058 (4)0.076 (4)0.111 (5)0.008 (3)0.055 (4)0.021 (4)
C14A0.030 (3)0.178 (7)0.049 (3)0.045 (4)−0.011 (2)−0.028 (4)
C15A0.035 (3)0.076 (4)0.063 (3)0.013 (3)0.010 (2)−0.025 (3)
C16A0.036 (3)0.046 (2)0.043 (2)0.000 (2)0.0089 (19)−0.0111 (19)
C17A0.052 (3)0.039 (2)0.044 (3)0.014 (2)−0.002 (2)−0.003 (2)
C18A0.0194 (18)0.0256 (16)0.0184 (15)0.0031 (14)−0.0036 (12)−0.0006 (12)
C19A0.029 (2)0.0271 (17)0.0209 (16)0.0026 (15)−0.0019 (14)−0.0017 (13)
C20A0.033 (2)0.0278 (18)0.0240 (17)0.0047 (16)−0.0043 (15)−0.0067 (14)
C21A0.024 (2)0.0237 (16)0.0306 (19)0.0052 (14)−0.0006 (14)−0.0020 (14)
C22A0.029 (2)0.035 (2)0.0247 (18)−0.0005 (17)0.0003 (15)0.0006 (15)
C23A0.027 (2)0.0324 (19)0.0188 (16)0.0003 (16)−0.0011 (13)−0.0038 (13)
C24A0.029 (2)0.0309 (19)0.035 (2)0.0008 (16)0.0068 (16)−0.0031 (16)
C25A0.048 (3)0.037 (2)0.056 (3)−0.007 (2)−0.003 (2)0.005 (2)
C26A0.068 (4)0.035 (2)0.072 (4)−0.005 (3)0.010 (3)0.012 (2)
C27A0.050 (3)0.033 (2)0.061 (3)−0.008 (2)0.012 (2)−0.006 (2)
C28A0.049 (3)0.041 (3)0.057 (3)−0.011 (2)0.013 (2)−0.016 (2)
C29A0.044 (3)0.035 (2)0.045 (2)−0.006 (2)0.006 (2)−0.0079 (19)
O1C—C5F1.11 (4)C10B—H10D0.9800
O1C—C5C1.282 (12)C10B—H10E0.9800
O2C—C11C1.219 (4)C10B—H10F0.9800
O3C—C11C1.332 (4)C12B—C15B1.501 (7)
O3C—C12C1.468 (4)C12B—C13B1.514 (7)
N1C—C9C1.363 (4)C12B—C14B1.528 (6)
N1C—C1C1.392 (4)C13B—H13D0.9800
N1C—H1NC0.92 (5)C13B—H13E0.9800
C1C—C2C1.351 (5)C13B—H13F0.9800
C1C—C10C1.495 (5)C14B—H14D0.9800
C2C—C11C1.474 (5)C14B—H14E0.9800
C2C—C3C1.519 (5)C14B—H14F0.9800
C3C—C18C1.518 (5)C15B—H15D0.9800
C3C—C4C1.523 (5)C15B—H15E0.9800
C3C—H3CA1.0000C15B—H15F0.9800
C4C—C9C1.352 (5)C16B—H16D0.9800
C4C—C5C1.416 (13)C16B—H16E0.9800
C4C—C5F1.57 (3)C16B—H16F0.9800
C9C—C8F1.41 (4)C17B—H17D0.9800
C9C—C8C1.537 (15)C17B—H17E0.9800
C10C—H10G0.9800C17B—H17F0.9800
C10C—H10H0.9800C18B—C23B1.384 (5)
C10C—H10I0.9800C18B—C19B1.393 (5)
C12C—C15C1.507 (6)C19B—C20B1.393 (5)
C12C—C13C1.518 (7)C19B—H19B0.9500
C12C—C14C1.519 (6)C20B—C21B1.389 (5)
C13C—H13G0.9800C20B—H20B0.9500
C13C—H13H0.9800C21B—C22B1.398 (5)
C13C—H13I0.9800C21B—C24B1.488 (5)
C14C—H14G0.9800C22B—C23B1.389 (5)
C14C—H14H0.9800C22B—H22B0.9500
C14C—H14I0.9800C23B—H23B0.9500
C15C—H15G0.9800C24B—C29B1.381 (6)
C15C—H15H0.9800C24B—C25B1.393 (6)
C15C—H15I0.9800C25B—C26B1.383 (7)
C5C—C6C1.543 (8)C25B—H25B0.9500
C6C—C16C1.529 (8)C26B—C27B1.394 (7)
C6C—C17C1.534 (8)C26B—H26B0.9500
C6C—C7C1.534 (9)C27B—C28B1.370 (7)
C7C—C8C1.514 (13)C27B—H27B0.9500
C7C—H7CA0.9900C28B—C29B1.396 (6)
C7C—H7CB0.9900C28B—H28B0.9500
C8C—H8CA0.9900C29B—H29B0.9500
C8C—H8CB0.9900O1A—C5A1.246 (4)
C16C—H16G0.9800O2A—C11A1.221 (4)
C16C—H16H0.9800O3A—C11A1.322 (5)
C16C—H16I0.9800O3A—C12A1.483 (5)
C17C—H17G0.9800N1A—C9A1.365 (5)
C17C—H17H0.9800N1A—C1A1.398 (5)
C17C—H17I0.9800N1A—H1NA0.92 (4)
C5F—C6F1.548 (18)C1A—C2A1.353 (5)
C6F—C16F1.526 (19)C1A—C10A1.496 (5)
C6F—C7F1.530 (17)C2A—C11A1.486 (5)
C6F—C17F1.547 (19)C2A—C3A1.525 (5)
C7F—C8F1.52 (2)C3A—C4A1.506 (5)
C7F—H7FA0.9900C3A—C18A1.527 (5)
C7F—H7FB0.9900C3A—H3AA1.0000
C8F—H8FA0.9900C4A—C9A1.372 (5)
C8F—H8FB0.9900C4A—C5A1.442 (5)
C16F—H16J0.9800C5A—C6A1.525 (5)
C16F—H16K0.9800C6A—C17A1.518 (6)
C16F—H16L0.9800C6A—C16A1.535 (6)
C17F—H17J0.9800C6A—C7A1.537 (5)
C17F—H17K0.9800C7A—C8A1.527 (6)
C17F—H17L0.9800C7A—H7AA0.9900
C18C—C23C1.398 (5)C7A—H7AB0.9900
C18C—C19C1.399 (5)C8A—C9A1.503 (5)
C19C—C20C1.389 (6)C8A—H8AA0.9900
C19C—H19C0.9500C8A—H8AB0.9900
C20C—C21C1.387 (6)C10A—H10A0.9800
C20C—H20C0.9500C10A—H10B0.9800
C21C—C22C1.394 (6)C10A—H10C0.9800
C21C—C24C1.487 (6)C12A—C13A1.480 (7)
C22C—C23C1.377 (6)C12A—C15A1.488 (7)
C22C—H22C0.9500C12A—C14A1.524 (7)
C23C—H23C0.9500C13A—H13A0.9800
C24C—C25C1.387 (7)C13A—H13B0.9800
C24C—C29C1.411 (7)C13A—H13C0.9800
C25C—C26C1.382 (9)C14A—H14A0.9800
C25C—H25C0.9500C14A—H14B0.9800
C26C—C27C1.374 (10)C14A—H14C0.9800
C26C—H26C0.9500C15A—H15A0.9800
C27C—C28C1.400 (9)C15A—H15B0.9800
C27C—H27C0.9500C15A—H15C0.9800
C28C—C29C1.399 (8)C16A—H16A0.9800
C28C—H28C0.9500C16A—H16B0.9800
C29C—H29C0.9500C16A—H16C0.9800
C1B—C2B1.354 (5)C17A—H17A0.9800
C1B—N1B1.397 (5)C17A—H17B0.9800
C1B—C10B1.500 (5)C17A—H17C0.9800
O1B—C5B1.235 (4)C18A—C23A1.387 (5)
O2B—C11B1.216 (4)C18A—C19A1.402 (5)
O3B—C11B1.338 (5)C19A—C20A1.395 (5)
O3B—C12B1.466 (5)C19A—H19A0.9500
N1B—C9B1.358 (5)C20A—C21A1.384 (5)
N1B—H1NB0.95 (4)C20A—H20A0.9500
C2B—C11B1.469 (5)C21A—C22A1.389 (5)
C2B—C3B1.521 (5)C21A—C24A1.499 (5)
C3B—C4B1.515 (5)C22A—C23A1.392 (5)
C3B—C18B1.525 (5)C22A—H22A0.9500
C3B—H3BA1.0000C23A—H23A0.9500
C4B—C9B1.350 (5)C24A—C25A1.387 (6)
C4B—C5B1.450 (5)C24A—C29A1.399 (6)
C5B—C6B1.538 (5)C25A—C26A1.393 (7)
C6B—C16B1.507 (7)C25A—H25A0.9500
C6B—C7B1.510 (5)C26A—C27A1.369 (8)
C6B—C17B1.553 (7)C26A—H26A0.9500
C7B—C8B1.543 (6)C27A—C28A1.373 (7)
C7B—H7BA0.9900C27A—H27A0.9500
C7B—H7BB0.9900C28A—C29A1.384 (6)
C8B—C9B1.509 (5)C28A—H28A0.9500
C8B—H8BA0.9900C29A—H29A0.9500
C8B—H8BB0.9900
C11C—O3C—C12C122.1 (3)C1B—C10B—H10E109.5
C9C—N1C—C1C122.2 (3)H10D—C10B—H10E109.5
C9C—N1C—H1NC123 (3)C1B—C10B—H10F109.5
C1C—N1C—H1NC113 (3)H10D—C10B—H10F109.5
C2C—C1C—N1C119.1 (3)H10E—C10B—H10F109.5
C2C—C1C—C10C128.3 (3)O2B—C11B—O3B124.1 (4)
N1C—C1C—C10C112.5 (3)O2B—C11B—C2B122.4 (4)
C1C—C2C—C11C124.7 (3)O3B—C11B—C2B113.4 (3)
C1C—C2C—C3C120.4 (3)O3B—C12B—C15B111.5 (4)
C11C—C2C—C3C114.9 (3)O3B—C12B—C13B108.2 (4)
C18C—C3C—C2C111.1 (3)C15B—C12B—C13B113.1 (4)
C18C—C3C—C4C112.5 (3)O3B—C12B—C14B101.1 (3)
C2C—C3C—C4C109.3 (3)C15B—C12B—C14B111.1 (4)
C18C—C3C—H3CA107.9C13B—C12B—C14B111.2 (4)
C2C—C3C—H3CA107.9C12B—C13B—H13D109.5
C4C—C3C—H3CA107.9C12B—C13B—H13E109.5
C9C—C4C—C5C119.4 (5)H13D—C13B—H13E109.5
C9C—C4C—C3C120.3 (3)C12B—C13B—H13F109.5
C5C—C4C—C3C120.3 (4)H13D—C13B—H13F109.5
C9C—C4C—C5F124.6 (9)H13E—C13B—H13F109.5
C3C—C4C—C5F114.6 (9)C12B—C14B—H14D109.5
C4C—C9C—N1C120.0 (3)C12B—C14B—H14E109.5
C4C—C9C—C8F118.8 (10)H14D—C14B—H14E109.5
N1C—C9C—C8F121.2 (10)C12B—C14B—H14F109.5
C4C—C9C—C8C125.4 (4)H14D—C14B—H14F109.5
N1C—C9C—C8C114.5 (4)H14E—C14B—H14F109.5
C1C—C10C—H10G109.5C12B—C15B—H15D109.5
C1C—C10C—H10H109.5C12B—C15B—H15E109.5
H10G—C10C—H10H109.5H15D—C15B—H15E109.5
C1C—C10C—H10I109.5C12B—C15B—H15F109.5
H10G—C10C—H10I109.5H15D—C15B—H15F109.5
H10H—C10C—H10I109.5H15E—C15B—H15F109.5
O2C—C11C—O3C123.9 (3)C6B—C16B—H16D109.5
O2C—C11C—C2C122.6 (3)C6B—C16B—H16E109.5
O3C—C11C—C2C113.5 (3)H16D—C16B—H16E109.5
O3C—C12C—C15C109.9 (4)C6B—C16B—H16F109.5
O3C—C12C—C13C110.2 (3)H16D—C16B—H16F109.5
C15C—C12C—C13C112.8 (4)H16E—C16B—H16F109.5
O3C—C12C—C14C101.7 (3)C6B—C17B—H17D109.5
C15C—C12C—C14C111.0 (4)C6B—C17B—H17E109.5
C13C—C12C—C14C110.6 (5)H17D—C17B—H17E109.5
C12C—C13C—H13G109.5C6B—C17B—H17F109.5
C12C—C13C—H13H109.5H17D—C17B—H17F109.5
H13G—C13C—H13H109.5H17E—C17B—H17F109.5
C12C—C13C—H13I109.5C23B—C18B—C19B118.3 (3)
H13G—C13C—H13I109.5C23B—C18B—C3B121.8 (3)
H13H—C13C—H13I109.5C19B—C18B—C3B119.8 (3)
C12C—C14C—H14G109.5C18B—C19B—C20B120.8 (3)
C12C—C14C—H14H109.5C18B—C19B—H19B119.6
H14G—C14C—H14H109.5C20B—C19B—H19B119.6
C12C—C14C—H14I109.5C21B—C20B—C19B120.9 (3)
H14G—C14C—H14I109.5C21B—C20B—H20B119.6
H14H—C14C—H14I109.5C19B—C20B—H20B119.6
C12C—C15C—H15G109.5C20B—C21B—C22B118.2 (3)
C12C—C15C—H15H109.5C20B—C21B—C24B120.5 (3)
H15G—C15C—H15H109.5C22B—C21B—C24B121.2 (3)
C12C—C15C—H15I109.5C23B—C22B—C21B120.5 (3)
H15G—C15C—H15I109.5C23B—C22B—H22B119.7
H15H—C15C—H15I109.5C21B—C22B—H22B119.7
O1C—C5C—C4C121.1 (6)C18B—C23B—C22B121.3 (3)
O1C—C5C—C6C118.3 (8)C18B—C23B—H23B119.4
C4C—C5C—C6C119.5 (9)C22B—C23B—H23B119.4
C16C—C6C—C17C109.5 (6)C29B—C24B—C25B117.9 (4)
C16C—C6C—C7C111.1 (5)C29B—C24B—C21B120.9 (4)
C17C—C6C—C7C110.0 (6)C25B—C24B—C21B121.1 (4)
C16C—C6C—C5C108.4 (7)C26B—C25B—C24B121.2 (5)
C17C—C6C—C5C109.4 (7)C26B—C25B—H25B119.4
C7C—C6C—C5C108.4 (6)C24B—C25B—H25B119.4
C8C—C7C—C6C113.2 (8)C25B—C26B—C27B119.8 (5)
C8C—C7C—H7CA108.9C25B—C26B—H26B120.1
C6C—C7C—H7CA108.9C27B—C26B—H26B120.1
C8C—C7C—H7CB108.9C28B—C27B—C26B120.0 (4)
C6C—C7C—H7CB108.9C28B—C27B—H27B120.0
H7CA—C7C—H7CB107.7C26B—C27B—H27B120.0
C7C—C8C—C9C109.1 (8)C27B—C28B—C29B119.5 (5)
C7C—C8C—H8CA109.9C27B—C28B—H28B120.2
C9C—C8C—H8CA109.9C29B—C28B—H28B120.2
C7C—C8C—H8CB109.9C24B—C29B—C28B121.6 (5)
C9C—C8C—H8CB109.9C24B—C29B—H29B119.2
H8CA—C8C—H8CB108.3C28B—C29B—H29B119.2
C6C—C16C—H16G109.5C11A—O3A—C12A121.3 (3)
C6C—C16C—H16H109.5C9A—N1A—C1A122.2 (3)
H16G—C16C—H16H109.5C9A—N1A—H1NA113 (3)
C6C—C16C—H16I109.5C1A—N1A—H1NA121 (3)
H16G—C16C—H16I109.5C2A—C1A—N1A119.2 (3)
H16H—C16C—H16I109.5C2A—C1A—C10A128.9 (3)
C6C—C17C—H17G109.5N1A—C1A—C10A111.8 (3)
C6C—C17C—H17H109.5C1A—C2A—C11A124.3 (3)
H17G—C17C—H17H109.5C1A—C2A—C3A120.7 (3)
C6C—C17C—H17I109.5C11A—C2A—C3A115.0 (3)
H17G—C17C—H17I109.5C4A—C3A—C2A110.7 (3)
H17H—C17C—H17I109.5C4A—C3A—C18A112.9 (3)
O1C—C5F—C6F120 (3)C2A—C3A—C18A108.8 (3)
O1C—C5F—C4C121.6 (19)C4A—C3A—H3AA108.1
C6F—C5F—C4C113 (2)C2A—C3A—H3AA108.1
C16F—C6F—C7F109.8 (14)C18A—C3A—H3AA108.1
C16F—C6F—C17F109.4 (14)C9A—C4A—C5A120.4 (3)
C7F—C6F—C17F112.4 (14)C9A—C4A—C3A120.2 (3)
C16F—C6F—C5F105.7 (17)C5A—C4A—C3A119.4 (3)
C7F—C6F—C5F109.8 (19)O1A—C5A—C4A120.6 (3)
C17F—C6F—C5F109.5 (19)O1A—C5A—C6A118.9 (3)
C8F—C7F—C6F112 (2)C4A—C5A—C6A120.5 (3)
C8F—C7F—H7FA109.3C17A—C6A—C5A111.0 (3)
C6F—C7F—H7FA109.3C17A—C6A—C16A110.1 (4)
C8F—C7F—H7FB109.3C5A—C6A—C16A106.5 (3)
C6F—C7F—H7FB109.3C17A—C6A—C7A108.8 (3)
H7FA—C7F—H7FB107.9C5A—C6A—C7A110.7 (3)
C9C—C8F—C7F119 (3)C16A—C6A—C7A109.7 (3)
C9C—C8F—H8FA107.5C8A—C7A—C6A113.2 (3)
C7F—C8F—H8FA107.5C8A—C7A—H7AA108.9
C9C—C8F—H8FB107.5C6A—C7A—H7AA108.9
C7F—C8F—H8FB107.5C8A—C7A—H7AB108.9
H8FA—C8F—H8FB107.0C6A—C7A—H7AB108.9
C6F—C16F—H16J109.5H7AA—C7A—H7AB107.8
C6F—C16F—H16K109.5C9A—C8A—C7A110.3 (3)
H16J—C16F—H16K109.5C9A—C8A—H8AA109.6
C6F—C16F—H16L109.5C7A—C8A—H8AA109.6
H16J—C16F—H16L109.5C9A—C8A—H8AB109.6
H16K—C16F—H16L109.5C7A—C8A—H8AB109.6
C6F—C17F—H17J109.5H8AA—C8A—H8AB108.1
C6F—C17F—H17K109.5N1A—C9A—C4A120.2 (3)
H17J—C17F—H17K109.5N1A—C9A—C8A116.5 (3)
C6F—C17F—H17L109.5C4A—C9A—C8A123.3 (3)
H17J—C17F—H17L109.5C1A—C10A—H10A109.5
H17K—C17F—H17L109.5C1A—C10A—H10B109.5
C23C—C18C—C19C117.8 (3)H10A—C10A—H10B109.5
C23C—C18C—C3C120.9 (3)C1A—C10A—H10C109.5
C19C—C18C—C3C121.2 (3)H10A—C10A—H10C109.5
C20C—C19C—C18C120.8 (4)H10B—C10A—H10C109.5
C20C—C19C—H19C119.6O2A—C11A—O3A124.7 (3)
C18C—C19C—H19C119.6O2A—C11A—C2A122.0 (3)
C21C—C20C—C19C121.3 (4)O3A—C11A—C2A113.3 (3)
C21C—C20C—H20C119.4C13A—C12A—O3A110.1 (4)
C19C—C20C—H20C119.4C13A—C12A—C15A112.6 (5)
C20C—C21C—C22C117.7 (4)O3A—C12A—C15A110.9 (4)
C20C—C21C—C24C121.0 (4)C13A—C12A—C14A111.8 (5)
C22C—C21C—C24C121.3 (4)O3A—C12A—C14A101.0 (3)
C23C—C22C—C21C121.6 (4)C15A—C12A—C14A109.9 (5)
C23C—C22C—H22C119.2C12A—C13A—H13A109.5
C21C—C22C—H22C119.2C12A—C13A—H13B109.5
C22C—C23C—C18C120.8 (4)H13A—C13A—H13B109.5
C22C—C23C—H23C119.6C12A—C13A—H13C109.5
C18C—C23C—H23C119.6H13A—C13A—H13C109.5
C25C—C24C—C29C118.3 (5)H13B—C13A—H13C109.5
C25C—C24C—C21C121.4 (5)C12A—C14A—H14A109.5
C29C—C24C—C21C120.3 (4)C12A—C14A—H14B109.5
C26C—C25C—C24C121.6 (7)H14A—C14A—H14B109.5
C26C—C25C—H25C119.2C12A—C14A—H14C109.5
C24C—C25C—H25C119.2H14A—C14A—H14C109.5
C27C—C26C—C25C120.1 (6)H14B—C14A—H14C109.5
C27C—C26C—H26C120.0C12A—C15A—H15A109.5
C25C—C26C—H26C120.0C12A—C15A—H15B109.5
C26C—C27C—C28C120.3 (6)H15A—C15A—H15B109.5
C26C—C27C—H27C119.9C12A—C15A—H15C109.5
C28C—C27C—H27C119.9H15A—C15A—H15C109.5
C29C—C28C—C27C119.5 (6)H15B—C15A—H15C109.5
C29C—C28C—H28C120.3C6A—C16A—H16A109.5
C27C—C28C—H28C120.3C6A—C16A—H16B109.5
C28C—C29C—C24C120.2 (6)H16A—C16A—H16B109.5
C28C—C29C—H29C119.9C6A—C16A—H16C109.5
C24C—C29C—H29C119.9H16A—C16A—H16C109.5
C2B—C1B—N1B119.4 (3)H16B—C16A—H16C109.5
C2B—C1B—C10B127.8 (4)C6A—C17A—H17A109.5
N1B—C1B—C10B112.8 (3)C6A—C17A—H17B109.5
C11B—O3B—C12B122.0 (3)H17A—C17A—H17B109.5
C9B—N1B—C1B122.4 (3)C6A—C17A—H17C109.5
C9B—N1B—H1NB121 (2)H17A—C17A—H17C109.5
C1B—N1B—H1NB115 (2)H17B—C17A—H17C109.5
C1B—C2B—C11B125.0 (3)C23A—C18A—C19A118.2 (3)
C1B—C2B—C3B120.2 (3)C23A—C18A—C3A121.4 (3)
C11B—C2B—C3B114.7 (3)C19A—C18A—C3A120.3 (3)
C4B—C3B—C2B110.6 (3)C20A—C19A—C18A120.3 (3)
C4B—C3B—C18B112.0 (3)C20A—C19A—H19A119.9
C2B—C3B—C18B110.5 (3)C18A—C19A—H19A119.9
C4B—C3B—H3BA107.8C21A—C20A—C19A121.3 (3)
C2B—C3B—H3BA107.8C21A—C20A—H20A119.3
C18B—C3B—H3BA107.8C19A—C20A—H20A119.3
C9B—C4B—C5B121.0 (3)C20A—C21A—C22A118.1 (3)
C9B—C4B—C3B120.5 (3)C20A—C21A—C24A121.5 (3)
C5B—C4B—C3B118.4 (3)C22A—C21A—C24A120.3 (3)
O1B—C5B—C4B121.8 (3)C21A—C22A—C23A121.1 (3)
O1B—C5B—C6B118.3 (3)C21A—C22A—H22A119.4
C4B—C5B—C6B119.9 (3)C23A—C22A—H22A119.4
C16B—C6B—C7B110.4 (4)C18A—C23A—C22A120.9 (3)
C16B—C6B—C5B111.1 (3)C18A—C23A—H23A119.5
C7B—C6B—C5B110.8 (3)C22A—C23A—H23A119.5
C16B—C6B—C17B107.6 (4)C25A—C24A—C29A118.3 (4)
C7B—C6B—C17B111.8 (3)C25A—C24A—C21A121.5 (4)
C5B—C6B—C17B105.0 (3)C29A—C24A—C21A120.2 (4)
C6B—C7B—C8B114.0 (3)C24A—C25A—C26A120.6 (5)
C6B—C7B—H7BA108.8C24A—C25A—H25A119.7
C8B—C7B—H7BA108.8C26A—C25A—H25A119.7
C6B—C7B—H7BB108.8C27A—C26A—C25A120.3 (5)
C8B—C7B—H7BB108.8C27A—C26A—H26A119.9
H7BA—C7B—H7BB107.7C25A—C26A—H26A119.9
C9B—C8B—C7B110.4 (3)C26A—C27A—C28A119.8 (4)
C9B—C8B—H8BA109.6C26A—C27A—H27A120.1
C7B—C8B—H8BA109.6C28A—C27A—H27A120.1
C9B—C8B—H8BB109.6C27A—C28A—C29A120.7 (5)
C7B—C8B—H8BB109.6C27A—C28A—H28A119.7
H8BA—C8B—H8BB108.1C29A—C28A—H28A119.7
C4B—C9B—N1B120.5 (3)C28A—C29A—C24A120.3 (5)
C4B—C9B—C8B123.4 (3)C28A—C29A—H29A119.9
N1B—C9B—C8B116.0 (3)C24A—C29A—H29A119.9
C1B—C10B—H10D109.5
C9C—N1C—C1C—C2C−13.3 (5)C5B—C6B—C7B—C8B−49.0 (5)
C9C—N1C—C1C—C10C165.7 (3)C17B—C6B—C7B—C8B67.8 (5)
N1C—C1C—C2C—C11C167.0 (3)C6B—C7B—C8B—C9B48.9 (5)
C10C—C1C—C2C—C11C−11.9 (6)C5B—C4B—C9B—N1B171.9 (3)
N1C—C1C—C2C—C3C−11.3 (5)C3B—C4B—C9B—N1B−6.1 (5)
C10C—C1C—C2C—C3C169.8 (4)C5B—C4B—C9B—C8B−5.5 (5)
C1C—C2C—C3C—C18C−94.9 (4)C3B—C4B—C9B—C8B176.5 (3)
C11C—C2C—C3C—C18C86.6 (4)C1B—N1B—C9B—C4B−13.2 (5)
C1C—C2C—C3C—C4C29.8 (4)C1B—N1B—C9B—C8B164.3 (3)
C11C—C2C—C3C—C4C−148.6 (3)C7B—C8B—C9B—C4B−21.2 (5)
C18C—C3C—C4C—C9C96.0 (4)C7B—C8B—C9B—N1B161.3 (3)
C2C—C3C—C4C—C9C−27.9 (5)C12B—O3B—C11B—O2B−6.2 (6)
C18C—C3C—C4C—C5C−83.8 (7)C12B—O3B—C11B—C2B172.5 (4)
C2C—C3C—C4C—C5C152.3 (7)C1B—C2B—C11B—O2B162.4 (4)
C18C—C3C—C4C—C5F−76.5 (17)C3B—C2B—C11B—O2B−14.1 (5)
C2C—C3C—C4C—C5F159.6 (16)C1B—C2B—C11B—O3B−16.4 (6)
C5C—C4C—C9C—N1C−172.9 (7)C3B—C2B—C11B—O3B167.1 (3)
C3C—C4C—C9C—N1C7.3 (5)C11B—O3B—C12B—C15B62.0 (6)
C5F—C4C—C9C—N1C179.1 (18)C11B—O3B—C12B—C13B−63.1 (5)
C3C—C4C—C9C—C8F−173 (3)C11B—O3B—C12B—C14B−179.9 (4)
C5F—C4C—C9C—C8F−1 (4)C4B—C3B—C18B—C23B46.4 (4)
C5C—C4C—C9C—C8C6.9 (14)C2B—C3B—C18B—C23B−77.4 (4)
C3C—C4C—C9C—C8C−172.9 (11)C4B—C3B—C18B—C19B−137.8 (3)
C1C—N1C—C9C—C4C15.4 (5)C2B—C3B—C18B—C19B98.3 (4)
C1C—N1C—C9C—C8F−164 (3)C23B—C18B—C19B—C20B0.0 (5)
C1C—N1C—C9C—C8C−164.4 (10)C3B—C18B—C19B—C20B−175.9 (3)
C12C—O3C—C11C—O2C3.1 (6)C18B—C19B—C20B—C21B0.4 (6)
C12C—O3C—C11C—C2C−174.1 (4)C19B—C20B—C21B—C22B−0.1 (6)
C1C—C2C—C11C—O2C−175.7 (4)C19B—C20B—C21B—C24B177.7 (4)
C3C—C2C—C11C—O2C2.7 (6)C20B—C21B—C22B—C23B−0.5 (6)
C1C—C2C—C11C—O3C1.6 (6)C24B—C21B—C22B—C23B−178.4 (4)
C3C—C2C—C11C—O3C−180.0 (3)C19B—C18B—C23B—C22B−0.7 (6)
C11C—O3C—C12C—C15C−66.1 (5)C3B—C18B—C23B—C22B175.2 (3)
C11C—O3C—C12C—C13C58.8 (5)C21B—C22B—C23B—C18B0.9 (6)
C11C—O3C—C12C—C14C176.2 (4)C20B—C21B—C24B—C29B46.5 (6)
C9C—C4C—C5C—O1C176.3 (8)C22B—C21B—C24B—C29B−135.7 (4)
C3C—C4C—C5C—O1C−3.9 (14)C20B—C21B—C24B—C25B−131.0 (5)
C9C—C4C—C5C—C6C−15.8 (12)C22B—C21B—C24B—C25B46.9 (6)
C3C—C4C—C5C—C6C164.0 (6)C29B—C24B—C25B—C26B−0.2 (8)
O1C—C5C—C6C—C16C87.0 (11)C21B—C24B—C25B—C26B177.3 (5)
C4C—C5C—C6C—C16C−81.2 (9)C24B—C25B—C26B—C27B−0.6 (9)
O1C—C5C—C6C—C17C−32.3 (12)C25B—C26B—C27B—C28B1.1 (9)
C4C—C5C—C6C—C17C159.4 (8)C26B—C27B—C28B—C29B−0.7 (8)
O1C—C5C—C6C—C7C−152.3 (9)C25B—C24B—C29B—C28B0.7 (7)
C4C—C5C—C6C—C7C39.5 (11)C21B—C24B—C29B—C28B−176.9 (4)
C16C—C6C—C7C—C8C62.9 (10)C27B—C28B—C29B—C24B−0.2 (7)
C17C—C6C—C7C—C8C−175.6 (9)C9A—N1A—C1A—C2A−13.7 (5)
C5C—C6C—C7C—C8C−56.1 (11)C9A—N1A—C1A—C10A166.0 (3)
C6C—C7C—C8C—C9C47.6 (15)N1A—C1A—C2A—C11A168.8 (3)
C4C—C9C—C8C—C7C−22.9 (18)C10A—C1A—C2A—C11A−10.8 (6)
N1C—C9C—C8C—C7C156.9 (8)N1A—C1A—C2A—C3A−8.3 (5)
C9C—C4C—C5F—O1C165 (2)C10A—C1A—C2A—C3A172.1 (3)
C3C—C4C—C5F—O1C−23 (4)C1A—C2A—C3A—C4A25.7 (4)
C9C—C4C—C5F—C6F12 (3)C11A—C2A—C3A—C4A−151.7 (3)
C3C—C4C—C5F—C6F−175.9 (17)C1A—C2A—C3A—C18A−99.0 (4)
O1C—C5F—C6F—C16F50 (3)C11A—C2A—C3A—C18A83.6 (4)
C4C—C5F—C6F—C16F−156 (2)C2A—C3A—C4A—C9A−24.3 (4)
O1C—C5F—C6F—C7F169 (3)C18A—C3A—C4A—C9A98.0 (4)
C4C—C5F—C6F—C7F−37 (3)C2A—C3A—C4A—C5A155.9 (3)
O1C—C5F—C6F—C17F−67 (3)C18A—C3A—C4A—C5A−81.7 (4)
C4C—C5F—C6F—C17F86 (3)C9A—C4A—C5A—O1A176.7 (3)
C16F—C6F—C7F—C8F170 (3)C3A—C4A—C5A—O1A−3.5 (5)
C17F—C6F—C7F—C8F−68 (3)C9A—C4A—C5A—C6A−4.4 (5)
C5F—C6F—C7F—C8F54 (3)C3A—C4A—C5A—C6A175.4 (3)
C4C—C9C—C8F—C7F18 (6)O1A—C5A—C6A—C17A−33.9 (5)
N1C—C9C—C8F—C7F−162 (3)C4A—C5A—C6A—C17A147.2 (4)
C6F—C7F—C8F—C9C−46 (5)O1A—C5A—C6A—C16A85.9 (4)
C2C—C3C—C18C—C23C74.7 (4)C4A—C5A—C6A—C16A−93.1 (4)
C4C—C3C—C18C—C23C−48.2 (4)O1A—C5A—C6A—C7A−154.9 (3)
C2C—C3C—C18C—C19C−100.8 (4)C4A—C5A—C6A—C7A26.2 (5)
C4C—C3C—C18C—C19C136.3 (3)C17A—C6A—C7A—C8A−171.9 (3)
C23C—C18C—C19C—C20C−0.1 (5)C5A—C6A—C7A—C8A−49.6 (4)
C3C—C18C—C19C—C20C175.6 (3)C16A—C6A—C7A—C8A67.6 (4)
C18C—C19C—C20C—C21C−1.6 (6)C6A—C7A—C8A—C9A50.7 (4)
C19C—C20C—C21C—C22C1.7 (6)C1A—N1A—C9A—C4A15.1 (5)
C19C—C20C—C21C—C24C−177.8 (4)C1A—N1A—C9A—C8A−165.3 (3)
C20C—C21C—C22C—C23C−0.2 (6)C5A—C4A—C9A—N1A−174.5 (3)
C24C—C21C—C22C—C23C179.3 (4)C3A—C4A—C9A—N1A5.7 (5)
C21C—C22C—C23C—C18C−1.5 (6)C5A—C4A—C9A—C8A5.9 (5)
C19C—C18C—C23C—C22C1.6 (5)C3A—C4A—C9A—C8A−173.9 (3)
C3C—C18C—C23C—C22C−174.1 (3)C7A—C8A—C9A—N1A151.4 (3)
C20C—C21C—C24C—C25C34.4 (6)C7A—C8A—C9A—C4A−29.0 (5)
C22C—C21C—C24C—C25C−145.0 (5)C12A—O3A—C11A—O2A5.4 (6)
C20C—C21C—C24C—C29C−147.3 (4)C12A—O3A—C11A—C2A−173.6 (3)
C22C—C21C—C24C—C29C33.3 (6)C1A—C2A—C11A—O2A−163.6 (4)
C29C—C24C—C25C—C26C−0.2 (9)C3A—C2A—C11A—O2A13.6 (5)
C21C—C24C—C25C—C26C178.1 (5)C1A—C2A—C11A—O3A15.4 (5)
C24C—C25C—C26C—C27C−1.0 (10)C3A—C2A—C11A—O3A−167.3 (3)
C25C—C26C—C27C—C28C1.5 (10)C11A—O3A—C12A—C13A60.1 (6)
C26C—C27C—C28C—C29C−0.8 (9)C11A—O3A—C12A—C15A−65.2 (5)
C27C—C28C—C29C—C24C−0.5 (8)C11A—O3A—C12A—C14A178.3 (5)
C25C—C24C—C29C—C28C0.9 (7)C4A—C3A—C18A—C23A−44.9 (5)
C21C—C24C—C29C—C28C−177.4 (4)C2A—C3A—C18A—C23A78.5 (4)
C2B—C1B—N1B—C9B11.4 (5)C4A—C3A—C18A—C19A140.0 (3)
C10B—C1B—N1B—C9B−167.1 (3)C2A—C3A—C18A—C19A−96.6 (4)
N1B—C1B—C2B—C11B−166.7 (3)C23A—C18A—C19A—C20A−0.1 (5)
C10B—C1B—C2B—C11B11.5 (6)C3A—C18A—C19A—C20A175.1 (3)
N1B—C1B—C2B—C3B9.6 (5)C18A—C19A—C20A—C21A−1.0 (6)
C10B—C1B—C2B—C3B−172.2 (4)C19A—C20A—C21A—C22A1.1 (6)
C1B—C2B—C3B—C4B−25.4 (4)C19A—C20A—C21A—C24A−177.8 (4)
C11B—C2B—C3B—C4B151.2 (3)C20A—C21A—C22A—C23A−0.2 (6)
C1B—C2B—C3B—C18B99.2 (4)C24A—C21A—C22A—C23A178.8 (4)
C11B—C2B—C3B—C18B−84.1 (4)C19A—C18A—C23A—C22A1.0 (6)
C2B—C3B—C4B—C9B23.8 (4)C3A—C18A—C23A—C22A−174.1 (4)
C18B—C3B—C4B—C9B−100.0 (4)C21A—C22A—C23A—C18A−0.9 (6)
C2B—C3B—C4B—C5B−154.2 (3)C20A—C21A—C24A—C25A140.7 (4)
C18B—C3B—C4B—C5B82.0 (4)C22A—C21A—C24A—C25A−38.3 (6)
C9B—C4B—C5B—O1B−172.8 (3)C20A—C21A—C24A—C29A−38.7 (6)
C3B—C4B—C5B—O1B5.1 (5)C22A—C21A—C24A—C29A142.3 (4)
C9B—C4B—C5B—C6B5.4 (5)C29A—C24A—C25A—C26A1.2 (7)
C3B—C4B—C5B—C6B−176.6 (3)C21A—C24A—C25A—C26A−178.2 (5)
O1B—C5B—C6B—C16B−36.6 (5)C24A—C25A—C26A—C27A−1.2 (8)
C4B—C5B—C6B—C16B145.1 (4)C25A—C26A—C27A—C28A−0.1 (9)
O1B—C5B—C6B—C7B−159.7 (3)C26A—C27A—C28A—C29A1.3 (8)
C4B—C5B—C6B—C7B22.0 (5)C27A—C28A—C29A—C24A−1.3 (7)
O1B—C5B—C6B—C17B79.4 (4)C25A—C24A—C29A—C28A0.0 (7)
C4B—C5B—C6B—C17B−98.9 (4)C21A—C24A—C29A—C28A179.4 (4)
C16B—C6B—C7B—C8B−172.5 (4)
D—H···AD—HH···AD···AD—H···A
N1C—H1NC···O1Bi0.92 (5)1.94 (5)2.843 (4)165 (5)
N1B—H1NB···O1C0.95 (4)1.88 (4)2.811 (4)168 (3)
N1A—H1NA···O1Aii0.93 (5)1.92 (5)2.842 (4)174 (4)
C3C—H3CA···O2C1.002.412.793 (4)102
C10A—H10B···O1Aii0.982.603.443 (5)145
C10B—H10F···O1C0.982.473.302 (5)143
C10C—H10G···O3C0.982.312.704 (4)103
C3B—H3BA···O2B1.002.402.795 (4)103
C13A—H13A···O2A0.982.452.978 (7)113
C13B—H13D···O2B0.982.473.023 (6)115
C13C—H13G···O2C0.982.532.958 (7)106
C15A—H15A···O2A0.982.412.999 (7)118
C15B—H15D···O2B0.982.412.965 (6)116
C15C—H15G···O2C0.982.493.022 (5)114
C3A—H3AA···O2A1.002.422.812 (5)103
C23A—H23A···O2Aii0.952.573.403 (4)147
C23B—H23B···O2C0.952.553.389 (5)147
C23C—H23C···O2Bi0.952.603.407 (4)144
C15A—H15B···Cg130.982.823.771 (6)165
C27A—H27A···Cg4ii0.952.753.578 (4)146
C27B—H27B···Cg80.952.633.493 (5)150
C27C—H27C···Cg12iii0.952.843.632 (7)142
  21 in total

1.  Two 1,4-dihydropyridine derivatives with potential calcium-channel antagonist activity.

Authors:  Anthony Linden; Cihat Safak; Rahime Simşek; Miyase G Gündüz
Journal:  Acta Crystallogr C       Date:  2011-01-27       Impact factor: 1.172

2.  Design, synthesis and 3D-QSAR studies of novel 1,4-dihydropyridines as TGFβ/Smad inhibitors.

Authors:  Daniel Längle; Viktoria Marquardt; Elena Heider; Brigita Vigante; Gunars Duburs; Iveta Luntena; Dirk Flötgen; Christopher Golz; Carsten Strohmann; Oliver Koch; Dennis Schade
Journal:  Eur J Med Chem       Date:  2015-03-14       Impact factor: 6.514

3.  The effect of bromine scanning around the phenyl group of 4-phenylquinolone derivatives.

Authors:  Scott A Steiger; Anthony J Monacelli; Chun Li; Janet L Hunting; Nicholas R Natale
Journal:  Acta Crystallogr C Struct Chem       Date:  2014-07-31       Impact factor: 1.172

4.  Synthesis and evaluation of 1,4-dihydropyridine derivatives with calcium channel blocking activity.

Authors:  Chris Bladen; Miyase Gözde Gündüz; Rahime Şimşek; Cihat Şafak; Gerald W Zamponi
Journal:  Pflugers Arch       Date:  2013-10-23       Impact factor: 3.657

Review 5.  Chronic inflammation in the etiology of disease across the life span.

Authors:  David Furman; Judith Campisi; Eric Verdin; Pedro Carrera-Bastos; Sasha Targ; Claudio Franceschi; Luigi Ferrucci; Derek W Gilroy; Alessio Fasano; Gary W Miller; Andrew H Miller; Alberto Mantovani; Cornelia M Weyand; Nir Barzilai; Jorg J Goronzy; Thomas A Rando; Rita B Effros; Alejandro Lucia; Nicole Kleinstreuer; George M Slavich
Journal:  Nat Med       Date:  2019-12-05       Impact factor: 53.440

6.  CrystalExplorer: a program for Hirshfeld surface analysis, visualization and quantitative analysis of molecular crystals.

Authors:  Peter R Spackman; Michael J Turner; Joshua J McKinnon; Stephen K Wolff; Daniel J Grimwood; Dylan Jayatilaka; Mark A Spackman
Journal:  J Appl Crystallogr       Date:  2021-04-27       Impact factor: 3.304

7.  SHELXT - integrated space-group and crystal-structure determination.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A Found Adv       Date:  2015-01-01       Impact factor: 2.290

Review 8.  Inflammatory responses and inflammation-associated diseases in organs.

Authors:  Linlin Chen; Huidan Deng; Hengmin Cui; Jing Fang; Zhicai Zuo; Junliang Deng; Yinglun Li; Xun Wang; Ling Zhao
Journal:  Oncotarget       Date:  2017-12-14

9.  The Cambridge Structural Database.

Authors:  Colin R Groom; Ian J Bruno; Matthew P Lightfoot; Suzanna C Ward
Journal:  Acta Crystallogr B Struct Sci Cryst Eng Mater       Date:  2016-04-01

Review 10.  Cytokines in Inflammatory Disease.

Authors:  Shinwan Kany; Jan Tilmann Vollrath; Borna Relja
Journal:  Int J Mol Sci       Date:  2019-11-28       Impact factor: 5.923
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