research communications
N′-[(1E,4E)-1,5-bis(4-methoxyphenyl)penta-1,4-dien-3-ylidene]hydrazine-1-carbodithioate
of benzylaDepartment of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor Darul Ehsan, Malaysia, and bDepartment of Chemistry, College of Education for Women, University of Anbar, Iraq
*Correspondence e-mail: ibra@upm.edu.my
In the title hydrazinecarbodithioate derivative, C27H26N2O2S2, the is comprised of four molecules (Z = 8 and Z′ = 4). The 4-methoxyphenyl rings are slightly twisted away from their attached olefinic double bonds [torsion angles = 5.9 (4)–19.6 (4)°]. The azomethine double bond has an s-trans configuration relative to one of the C=C bonds and an s-cis configuration relative to the other [C=C—C= N = 147.4 (6)–175.7 (2) and 15.3 (3)–37.4 (7)°, respectively]. The torsion angles between the azomethine C=N double bond and hydrazine-1-carbodithioate moiety indicate only small deviations from planarity, with torsion angles ranging from 0.9 (3) to 6.9 (3)° and from 174.9 (3) to 179.7 (2)°, respectively. The benzyl ring and the methylenesulfanyl moiety are almost perpendicular to each other, as indicated by their torsion angles [range 93.7 (3)–114.6 (2)°]. In the crystal, molecules are linked by C—H⋯O, N—H⋯S and C—H⋯π(ring) hydrogen-bonding interactions into a three-dimensional network. Structural details of related benzyl hydrazine-1-carbodithioate are surveyed and compared with those of the title compound.
1. Chemical context
S-benzyl and S-alkyl dithiocarbazates are interesting ligands in coordination chemistry because they can act as N,S-chelating agents because of the presence of soft sulfur and hard nitrogen donor atoms (Takjoo et al., 2016). These types of ligands can form stable metal complexes with five-membered chelate rings, and with transition metals in different stable oxidation states (Centore et al., 2013). Dithiocarbazate and their metal complexes show a wide range of biological activities such as anti-malarial, anti-bacterial, anti-viral and anti-tumour (Low et al., 2016; Nanjundan et al., 2016; Islam et al., 2016a). S-benzyldithiocarbazate and S-alkyldithiocarbazate Schiff base derivatives formed with aromatic and as well as their metal complexes have attracted attention due to their cytotoxicity against many types of cancer cell lines (Yusof et al., 2016; 2017a,b; Vijayan et al., 2015; Basha et al., 2012), whereby S-methyl and S-benzyl dithiocarbazate with 2-acetylpyridine show better cytotoxicity against a breast cancer cell line (MDA-MB-231) than their transition-metal complexes (Hamid et al., 2016). Furthermore, synthesized from the reaction of S-benzyldithiocarbazate and m-hydroxyacetophenone as well as their metal complexes exhibit moderate analgesic and good anti-inflammatory activities in comparison with standard drugs diclofenac sodium and indomethacin (Mahapatra et al., 2017).
Encouraged by previous findings on various properties of related Schiff base derivatives, we report herein the synthesis and I). Structural details of (I) are compared with other hydrazinecarbodithioates.
of the title compound (2. Structural commentary
The I) consists of four molecules, denoted as A, B, C and D. Orientational disorder of the 1,5-bis(phenyl)penta-1,4-dien-3-ylidenyl amine moiety in molecule B and of the phenylmethyl moiety in molecule D were observed. The molecules are composed of a 1,5-bis(4-methoxyphenyl)penta-1,4-dien-3-ylidenyl moiety, connected to a benzyl ring by a hydrazine-1-carbodithioate (–C=N—(NH)—(C=S)—S—C–) bridge (Fig. 1). Conformational details of the 1,5-bis(4-methoxyphenyl)penta-1,4-dien-3-ylidenyl moiety can be described by the torsion angles between the 4-methoxy moiety and the phenyl ring [τ1 (C2—C3—O1—C26); τ6 (C16—C15—O2—C27)], between the 4-methoxyphenyl ring and the olefinic double bond [τ2 (C5—C6-C7—C8); τ5 (C17—C12—C11—C10)], and between the olefinic double bond and the azomethine double bond [τ3 (N1—C9—C8—C7); τ4 (N1—C9—C10—C11)]. Torsion angles τ1 and τ6 are approximately 0° or ±180° in the majority of the four molecules, except molecule C which has a τ1 of 20.9 (3)° (Table 1). The 4-methoxyphenyl rings in the 1,5-bis(4-methoxyphenyl)penta-1,4-dien-3-ylidenyl moiety are twisted away from their attached olefinic double bonds [τ2 = 5.9 (4)–16.4 (13)°; τ5 = 7.5 (3)–19.6 (4)°]. The orientations of the the azomethine double bond with its neighbouring olefinic double bonds relative to the intermediate C—C bond (C8—C9; C9—C10) are different: one is in s-trans [τ3 = 147.4 (6)–175.7 (2)°] conformation and the other in s-cis [τ4 = 15.3 (3)–37.4 (7)°] conformation. The dihedral angles between two 4-methoxyphenyl rings in an individual molecule are in the range 23.59 (12)–89.6 (5)° (Table 2). Conformational details of the benzyl hydrazine-1-carbodithioate moiety can be outlined by torsion angles τ7 (C9—N1—N2—C18), τ8 (N1—N2—C18—S1), τ9 (N2—C18—S1—C19), τ10 (C18—S1—C19—C20) and τ11 (S1—C19—C20—C21). In all molecules of (I), the hydrazine-1-carbothioate bridges are more or less planar (ideal values τ7, τ8 and τ9 = 0 or ±180°; experimental values: 0.9 (3)–6.9 (3)° and 174.9 (3)–179.7 (2)°, respectively). The torsion angles between the sulfane moiety and the methylene moiety indicate a slight twist [τ10 = 160.53 (17)–163.36 (16)°]. These contortions are more severe between the benzyl ring and the methylene sulfane moiety where τ11 is considerably smaller [τ11 = 93.7 (3)–114.6 (2)°]. The dihedral angles between the benzyl ring and the two 4-methoxyphenyl rings are in the range 31.6 (5)–89.9 (8)° (Table 2). An overlay of the four molecules in the was created with OLEX2 (Dolomanov et al., 2009) and is shown in Fig. 2.
of (
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3. Supramolecular features
In the crystal, molecule A is interconnected to molecule B and molecule C through weak C24A—H24A⋯O2B and C21A—H21A⋯O1C hydrogen-bonding interactions. Molecules B and C each form inversion-related dimers via C21B—H21B⋯O1B and N2C—H3N2⋯S2C interactions, respectively (Fig. 3a). In addition, molecule C and molecule D are connected through C17C—H17C⋯O1D hydrogen bonds (Fig. 3b). The four molecules are linked into an endless chain parallel to [021] through the combination of these hydrogen bonds (Fig. 4). Further interactions, namely N2A—H1N2⋯S2A, N2B—H2N2⋯S2D and N2D—H4N2⋯S2B, link the chains into a three-dimensional network, as shown in Fig. 5. Additional C—H⋯π interactions (Table 3) consolidate the packing.
4. Database survey
A search of the Cambridge Structural Database (CSD, version 5.40, last update May 2019; Groom et al., 2016) using benzyl 2-(λ2-methylene)hydrazine-1-carbodithioate as reference moiety resulted in 45 structures with different substituents. The reference moiety and relevant torsion angles are illustrated in Fig. 6. Details regarding different substituents (R1) together with the torsion angles for the benzyl hydrazine-1-carbothioate moiety in these structures are collated in Table 4. In analogy with the title molecules, the planarity of the hydrazine-1-carbodithioate bridge for these structures is indicated by the τ7, τ8 and τ9; torsion angles τ7 and τ9 range from 165.1 to 180.0° and indicate an anti-periplanar conformation whereas torsion angle τ8 is indicative of a syn-periplanar conformation (0.0– 9.1°). With respect to torsion angle τ10, most of the structures adopt an anti-periplanar conformation ranging from 159.5 to 180.0°, but there are nine structures that adopt either a syn-clinal or an anti-clinal conformation (77.6–110.4°). In most of the structures, the benzyl ring and the methylene sulfane moiety are orientated almost perpendicular to each other, as indicated by torsion angle τ11. Here, either a syn-clinal (68.1–88.4°) or an anti-clinal (92.2–141.1°) conformation is adopted. However, there is one outlier (WADGAK; Chan et al., 2003) where the benzyl hydrazine-1-carbodithioate moiety is substituted with a 1-(thiophen-2-yl)ethylidenyl moiety. In contrast to most of the structures, torsion angle τ11 = 17.1° for WADGAK indicates a syn-periplanar conformation.
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5. Synthesis and crystallization
Compound (I) was synthesized following a well-described literature protocol (Ali & Tarafder, 1977; Ravoof et al., 2010; Omar et al., 2014). S-benzyldithiocarbazate (1.98 g, 0.01 mol) was dissolved in absolute ethanol (50 ml) under heating and stirring. The resulting solution was slowly added to a hot solution of di-p-methoxybenzalacetone (2.94 g, 0.01 mol) dissolved in absolute ethanol (50 ml). 3-5 drops of concentrated hydrochloric acid were added to the mixture, which was subsequently heated and stirred for 5 h (Fig. 7). The acidified mixture was allowed to stand overnight, resulting in the formation of red crystals. They were filtered off and recrystallized using the slow evaporation technique from absolute ethanol as solvent.
Yield: 57.3%. m.p.: 375-376 K. Analysis calculated for C27H26N2O2S2: C, 49.71; H, 5.52; N, 5.90; S, 13.51% found: C, 49.68; H, 5.48; N, 5.97; S, 13.55%. FT-IR (cm−1): 3145, ν(N—H); 1630, ν(C=N); 1244, ν(N—N); 1059, ν(C=S); 3145. 1H NMR (CDCl3) δ (p.p.m.)= 6.55–7.68 (aromatic H); 3.85 (OCH3); 4.55 (–CH2 benzyl); 10.20 (N—H). 13C NMR (CDCl3) δ(p.p.m.)= 114.35–142.88 (aromatic C); 55.55 (OCH3); 39.34 (–CH2 benzyl); 161.22 (C=N); 206.91 (C=S). m/z calculated for C27H26N2O2S2: 474, found 474.
6. Refinement
Crystal data, data collection and structure . The labelling of atoms is the same in each molecule, with the molecule indicated by the suffix A, B, C or D. The N-bound H atoms were located in difference-Fourier maps and were refined freely [N—H = 0.81 (3)–0.91 (4) Å]. The C-bound H atoms were positioned geometrically (C—H = 0.93–0.97 Å) and refined using a riding model, with Uiso(H) = 1.2 or 1.5Ueq(C). A rotating-group model was applied to the methyl groups. The 1,5-bis(phenyl)penta-1,4-dien-3-ylidenyl amine moiety in molecule B and the phenylmethyl moiety in molecule D display positional disorder, with refined site occupancy ratios of 0.667 (7):0.333 (7) and 0.653 (15):0.347 (15), respectively (SIMU, DELU and SAME restraints were used).
details are summarized in Table 5
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Supporting information
https://doi.org/10.1107/S2056989019013458/wm5520sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019013458/wm5520Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989019013458/wm5520Isup3.cml
Data collection: CrysAlis PRO (Rigaku OD, 2018); cell
CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: SHELXL2013 (Sheldrick, 2015), Mercury (Macrae et al., 2006) and OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2015) and PLATON (Spek, 2009).C27H26N2O2S2 | Z = 8 |
Mr = 474.62 | F(000) = 2000 |
Triclinic, P1 | Dx = 1.310 Mg m−3 |
a = 10.2010 (1) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 20.0260 (3) Å | Cell parameters from 39902 reflections |
c = 25.2349 (4) Å | θ = 3.7–76.4° |
α = 70.535 (1)° | µ = 2.22 mm−1 |
β = 86.852 (1)° | T = 100 K |
γ = 82.147 (1)° | Plate, clear intense red |
V = 4814.65 (12) Å3 | 0.14 × 0.08 × 0.05 mm |
XtaLAB Synergy, Dualflex, AtlasS2 diffractometer | 17182 independent reflections |
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source | 14177 reflections with I > 2σ(I) |
Detector resolution: 5.2558 pixels mm-1 | Rint = 0.046 |
ω scans | θmax = 67.1°, θmin = 3.5° |
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2018) | h = −12→12 |
Tmin = 0.681, Tmax = 1.000 | k = −23→22 |
114750 measured reflections | l = −30→30 |
Refinement on F2 | 80 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.048 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.130 | w = 1/[σ2(Fo2) + (0.0653P)2 + 3.3132P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
17182 reflections | Δρmax = 1.16 e Å−3 |
1449 parameters | Δρmin = −0.62 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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1A | 0.38286 (5) | 0.22017 (3) | 0.45386 (2) | 0.02996 (13) | |
S2A | 0.33363 (5) | 0.06508 (3) | 0.50610 (2) | 0.02843 (12) | |
N1A | 0.59006 (18) | 0.16709 (9) | 0.40187 (8) | 0.0289 (4) | |
N2A | 0.52876 (18) | 0.11192 (10) | 0.43731 (8) | 0.0273 (4) | |
H1N2 | 0.553 (3) | 0.0696 (15) | 0.4436 (11) | 0.035 (7)* | |
O1A | 1.10882 (18) | −0.19587 (9) | 0.33832 (8) | 0.0455 (4) | |
O2A | 0.78919 (19) | 0.52640 (9) | 0.13693 (8) | 0.0502 (5) | |
C1A | 1.0517 (2) | −0.00371 (12) | 0.31844 (10) | 0.0327 (5) | |
H1AA | 1.090814 | 0.037742 | 0.301784 | 0.039* | |
C2A | 1.1166 (2) | −0.06786 (13) | 0.31486 (11) | 0.0360 (5) | |
H2AA | 1.197486 | −0.069235 | 0.296124 | 0.043* | |
C3A | 1.0584 (2) | −0.12966 (12) | 0.33974 (10) | 0.0344 (5) | |
C4A | 0.9379 (2) | −0.12664 (12) | 0.36779 (10) | 0.0354 (5) | |
H4AA | 0.899450 | −0.168273 | 0.384749 | 0.043* | |
C5A | 0.8748 (2) | −0.06274 (12) | 0.37073 (10) | 0.0315 (5) | |
H5AA | 0.793795 | −0.061597 | 0.389444 | 0.038* | |
C6A | 0.9311 (2) | 0.00086 (11) | 0.34583 (9) | 0.0275 (4) | |
C7A | 0.8665 (2) | 0.07035 (11) | 0.34688 (9) | 0.0283 (4) | |
H7AA | 0.907514 | 0.109891 | 0.326213 | 0.034* | |
C8A | 0.7556 (2) | 0.08318 (11) | 0.37416 (9) | 0.0288 (4) | |
H8AA | 0.714877 | 0.044069 | 0.395916 | 0.035* | |
C9A | 0.6929 (2) | 0.15396 (11) | 0.37257 (9) | 0.0281 (4) | |
C10A | 0.7424 (2) | 0.21836 (11) | 0.33310 (9) | 0.0299 (5) | |
H10A | 0.833252 | 0.218739 | 0.327660 | 0.036* | |
C11A | 0.6612 (2) | 0.27617 (11) | 0.30489 (10) | 0.0326 (5) | |
H11A | 0.571218 | 0.274950 | 0.312663 | 0.039* | |
C12A | 0.6996 (2) | 0.34134 (11) | 0.26292 (10) | 0.0320 (5) | |
C13A | 0.6064 (2) | 0.38630 (12) | 0.22410 (11) | 0.0375 (5) | |
H13A | 0.520152 | 0.375220 | 0.226469 | 0.045* | |
C14A | 0.6390 (3) | 0.44668 (12) | 0.18239 (11) | 0.0404 (6) | |
H14A | 0.575534 | 0.475249 | 0.156663 | 0.048* | |
C15A | 0.7669 (2) | 0.46478 (12) | 0.17885 (11) | 0.0379 (5) | |
C16A | 0.8617 (2) | 0.42146 (12) | 0.21703 (11) | 0.0375 (5) | |
H16A | 0.947445 | 0.433161 | 0.214852 | 0.045* | |
C17A | 0.8274 (2) | 0.36054 (11) | 0.25847 (10) | 0.0337 (5) | |
H17A | 0.891163 | 0.331773 | 0.283925 | 0.040* | |
C18A | 0.4203 (2) | 0.12795 (11) | 0.46564 (9) | 0.0264 (4) | |
C19A | 0.2365 (2) | 0.22242 (13) | 0.49776 (13) | 0.0448 (7) | |
H19A | 0.159869 | 0.217668 | 0.478795 | 0.054* | |
H19B | 0.247377 | 0.182943 | 0.532824 | 0.054* | |
C20A | 0.2159 (2) | 0.29220 (11) | 0.50951 (10) | 0.0309 (5) | |
C21A | 0.2611 (2) | 0.29552 (13) | 0.55912 (11) | 0.0399 (6) | |
H21A | 0.307545 | 0.255074 | 0.584080 | 0.048* | |
C22A | 0.2387 (3) | 0.35777 (14) | 0.57229 (11) | 0.0419 (6) | |
H22A | 0.268796 | 0.358855 | 0.606080 | 0.050* | |
C23A | 0.1716 (2) | 0.41825 (12) | 0.53528 (11) | 0.0371 (5) | |
H23A | 0.156331 | 0.460290 | 0.543993 | 0.044* | |
C24A | 0.1273 (2) | 0.41627 (12) | 0.48555 (11) | 0.0387 (5) | |
H24A | 0.082566 | 0.457230 | 0.460470 | 0.046* | |
C25A | 0.1486 (2) | 0.35363 (12) | 0.47231 (10) | 0.0342 (5) | |
H25A | 0.117832 | 0.352740 | 0.438563 | 0.041* | |
C26A | 1.2328 (3) | −0.20308 (17) | 0.31144 (17) | 0.0622 (9) | |
H26A | 1.257882 | −0.252198 | 0.314525 | 0.093* | |
H26B | 1.298221 | −0.187579 | 0.329079 | 0.093* | |
H26C | 1.226313 | −0.174351 | 0.272485 | 0.093* | |
C27A | 0.9199 (3) | 0.54696 (15) | 0.13175 (14) | 0.0591 (8) | |
H27A | 0.923718 | 0.589567 | 0.100000 | 0.089* | |
H27B | 0.982668 | 0.509279 | 0.126530 | 0.089* | |
H27C | 0.940797 | 0.555781 | 0.165270 | 0.089* | |
S1B | 0.39730 (6) | 0.76943 (3) | 0.04835 (2) | 0.03568 (14) | |
S2B | 0.43703 (5) | 0.92506 (3) | −0.00786 (2) | 0.03000 (13) | |
N2B | 0.2514 (2) | 0.87613 (11) | 0.06618 (9) | 0.0382 (5) | |
H2N2 | 0.227 (3) | 0.9186 (15) | 0.0605 (12) | 0.035 (7)* | |
O1B | −0.31580 (19) | 1.19059 (12) | 0.15074 (8) | 0.0544 (5) | |
O2B | −0.05549 (17) | 0.47568 (8) | 0.37333 (7) | 0.0382 (4) | |
C18B | 0.3579 (2) | 0.86140 (11) | 0.03607 (9) | 0.0309 (5) | |
C19B | 0.5367 (2) | 0.76729 (12) | 0.00149 (13) | 0.0442 (6) | |
H19C | 0.521337 | 0.805729 | −0.033959 | 0.053* | |
H19D | 0.616236 | 0.773125 | 0.017978 | 0.053* | |
C20B | 0.5526 (2) | 0.69606 (12) | −0.00798 (11) | 0.0359 (5) | |
C21B | 0.4943 (3) | 0.68917 (15) | −0.05345 (12) | 0.0488 (6) | |
H21B | 0.442817 | 0.728294 | −0.077543 | 0.059* | |
C22B | 0.5111 (3) | 0.62506 (18) | −0.06389 (13) | 0.0573 (8) | |
H22B | 0.471649 | 0.621575 | −0.095064 | 0.069* | |
C23B | 0.5855 (3) | 0.56663 (15) | −0.02866 (13) | 0.0524 (7) | |
H23B | 0.598908 | 0.523844 | −0.036292 | 0.063* | |
C24B | 0.6400 (3) | 0.57196 (13) | 0.01807 (12) | 0.0516 (7) | |
H24B | 0.688022 | 0.532036 | 0.042923 | 0.062* | |
C25B | 0.6243 (3) | 0.63638 (13) | 0.02859 (12) | 0.0440 (6) | |
H25B | 0.661956 | 0.639434 | 0.060301 | 0.053* | |
C26B | −0.3399 (3) | 1.21002 (18) | 0.20007 (13) | 0.0585 (8) | |
H26D | −0.383061 | 1.258173 | 0.190106 | 0.088* | |
H26E | −0.257378 | 1.206576 | 0.217922 | 0.088* | |
H26F | −0.395555 | 1.178403 | 0.225470 | 0.088* | |
C27B | −0.1821 (3) | 0.45199 (14) | 0.37586 (12) | 0.0464 (6) | |
H27D | −0.185034 | 0.408726 | 0.407067 | 0.070* | |
H27E | −0.196837 | 0.443262 | 0.341629 | 0.070* | |
H27F | −0.249514 | 0.488044 | 0.380591 | 0.070* | |
S1C | 1.11763 (6) | −0.22107 (3) | 0.54167 (2) | 0.03300 (13) | |
S2C | 1.13700 (7) | −0.06552 (3) | 0.47861 (3) | 0.04438 (16) | |
N1C | 0.92728 (19) | −0.16897 (9) | 0.60427 (8) | 0.0310 (4) | |
N2C | 0.96835 (19) | −0.11438 (10) | 0.56067 (8) | 0.0308 (4) | |
H3N2 | 0.941 (3) | −0.0668 (18) | 0.5497 (14) | 0.062 (9)* | |
O1C | 0.38467 (17) | 0.18373 (9) | 0.67618 (8) | 0.0424 (4) | |
O2C | 0.7281 (2) | −0.53080 (10) | 0.86542 (9) | 0.0595 (5) | |
C1C | 0.4978 (2) | −0.00762 (13) | 0.71071 (10) | 0.0383 (5) | |
H1CA | 0.489065 | −0.050567 | 0.739130 | 0.046* | |
C2C | 0.4318 (2) | 0.05467 (13) | 0.71624 (10) | 0.0375 (5) | |
H2CA | 0.380330 | 0.053488 | 0.748040 | 0.045* | |
C3C | 0.4429 (2) | 0.11881 (12) | 0.67410 (10) | 0.0324 (5) | |
C4C | 0.5178 (2) | 0.11903 (13) | 0.62654 (11) | 0.0402 (6) | |
H4CA | 0.523531 | 0.161930 | 0.597630 | 0.048* | |
C5C | 0.5838 (2) | 0.05681 (12) | 0.62143 (10) | 0.0377 (5) | |
H5CA | 0.633646 | 0.058137 | 0.589190 | 0.045* | |
C6C | 0.5768 (2) | −0.00852 (12) | 0.66427 (10) | 0.0316 (5) | |
C7C | 0.6511 (2) | −0.07643 (12) | 0.66400 (10) | 0.0339 (5) | |
H7CA | 0.622182 | −0.117503 | 0.689193 | 0.041* | |
C8C | 0.7550 (2) | −0.08630 (11) | 0.63195 (9) | 0.0306 (5) | |
H8CA | 0.782189 | −0.046291 | 0.604652 | 0.037* | |
C9C | 0.8293 (2) | −0.15577 (11) | 0.63682 (9) | 0.0297 (5) | |
C10C | 0.7988 (2) | −0.21889 (12) | 0.68407 (10) | 0.0318 (5) | |
H10C | 0.760475 | −0.211209 | 0.716178 | 0.038* | |
C11C | 0.8219 (2) | −0.28565 (12) | 0.68419 (10) | 0.0319 (5) | |
H11C | 0.856297 | −0.292752 | 0.651316 | 0.038* | |
C12C | 0.7979 (2) | −0.34955 (12) | 0.73162 (10) | 0.0321 (5) | |
C13C | 0.8149 (3) | −0.41598 (12) | 0.72411 (11) | 0.0399 (6) | |
H13C | 0.841893 | −0.419045 | 0.689104 | 0.048* | |
C14C | 0.7926 (3) | −0.47799 (13) | 0.76760 (12) | 0.0451 (6) | |
H14C | 0.803828 | −0.521705 | 0.761452 | 0.054* | |
C15C | 0.7540 (3) | −0.47420 (13) | 0.81963 (11) | 0.0430 (6) | |
C16C | 0.7396 (2) | −0.40854 (13) | 0.82858 (11) | 0.0411 (6) | |
H16C | 0.715610 | −0.406011 | 0.864018 | 0.049* | |
C17C | 0.7607 (2) | −0.34747 (12) | 0.78525 (10) | 0.0343 (5) | |
H17C | 0.750003 | −0.303980 | 0.791764 | 0.041* | |
C18C | 1.0683 (2) | −0.12894 (13) | 0.52717 (10) | 0.0342 (5) | |
C19C | 1.2426 (2) | −0.21912 (12) | 0.48679 (11) | 0.0356 (5) | |
H19E | 1.211522 | −0.184086 | 0.451463 | 0.043* | |
H19F | 1.323596 | −0.205913 | 0.496674 | 0.043* | |
C20C | 1.2686 (2) | −0.29216 (11) | 0.48084 (9) | 0.0304 (5) | |
C21C | 1.3916 (2) | −0.33277 (13) | 0.49416 (12) | 0.0403 (6) | |
H21C | 1.457608 | −0.315225 | 0.507770 | 0.048* | |
C22C | 1.4165 (3) | −0.39910 (14) | 0.48731 (14) | 0.0518 (7) | |
H22C | 1.498957 | −0.425961 | 0.496461 | 0.062* | |
C23C | 1.3198 (3) | −0.42546 (13) | 0.46702 (13) | 0.0470 (7) | |
H23C | 1.337010 | −0.469916 | 0.462221 | 0.056* | |
C24C | 1.1982 (3) | −0.38611 (14) | 0.45391 (12) | 0.0437 (6) | |
H24C | 1.132802 | −0.404143 | 0.440387 | 0.052* | |
C25C | 1.1717 (2) | −0.31965 (13) | 0.46060 (11) | 0.0378 (5) | |
H25C | 1.088770 | −0.293331 | 0.451523 | 0.045* | |
C26C | 0.2749 (2) | 0.18433 (14) | 0.71364 (12) | 0.0421 (6) | |
H26G | 0.235743 | 0.232671 | 0.707503 | 0.063* | |
H26H | 0.304629 | 0.163257 | 0.751748 | 0.063* | |
H26I | 0.210361 | 0.157478 | 0.706877 | 0.063* | |
C27C | 0.7472 (4) | −0.59989 (16) | 0.85860 (16) | 0.0765 (11) | |
H27G | 0.720411 | −0.634840 | 0.892439 | 0.115* | |
H27H | 0.838932 | −0.612035 | 0.851000 | 0.115* | |
H27I | 0.694871 | −0.598980 | 0.827822 | 0.115* | |
S2D | 0.87082 (7) | 0.94461 (4) | −0.02823 (3) | 0.05084 (18) | |
N1D | 0.67804 (19) | 0.84475 (11) | 0.10430 (9) | 0.0368 (4) | |
N2D | 0.71944 (19) | 0.89845 (11) | 0.06061 (9) | 0.0353 (4) | |
H4N2 | 0.680 (3) | 0.9447 (19) | 0.0493 (15) | 0.066 (10)* | |
O1D | 0.17094 (18) | 1.21299 (9) | 0.17203 (9) | 0.0464 (4) | |
O2D | 0.4571 (2) | 0.49382 (9) | 0.36916 (8) | 0.0481 (4) | |
C1D | 0.2135 (2) | 1.02822 (12) | 0.17183 (11) | 0.0360 (5) | |
H1DA | 0.165625 | 0.989735 | 0.179164 | 0.043* | |
C2D | 0.1496 (2) | 1.09145 (13) | 0.17662 (11) | 0.0389 (5) | |
H2DA | 0.060380 | 1.095586 | 0.186367 | 0.047* | |
C3D | 0.2215 (2) | 1.14876 (12) | 0.16658 (10) | 0.0352 (5) | |
C4D | 0.3540 (2) | 1.14194 (13) | 0.15068 (11) | 0.0391 (6) | |
H4DA | 0.401831 | 1.180437 | 0.143535 | 0.047* | |
C5D | 0.4150 (2) | 1.07893 (12) | 0.14542 (10) | 0.0359 (5) | |
H5DA | 0.503412 | 1.075558 | 0.134304 | 0.043* | |
C6D | 0.3464 (2) | 1.01957 (12) | 0.15651 (9) | 0.0308 (5) | |
C7D | 0.4073 (2) | 0.95049 (11) | 0.15394 (9) | 0.0297 (5) | |
H7DA | 0.356137 | 0.913176 | 0.167502 | 0.036* | |
C8D | 0.5280 (2) | 0.93413 (12) | 0.13443 (9) | 0.0311 (5) | |
H8DA | 0.579507 | 0.970872 | 0.118385 | 0.037* | |
C9D | 0.5835 (2) | 0.86182 (12) | 0.13692 (10) | 0.0310 (5) | |
C10D | 0.5399 (2) | 0.80078 (12) | 0.18230 (10) | 0.0333 (5) | |
H10D | 0.490036 | 0.810412 | 0.211485 | 0.040* | |
C11D | 0.5664 (2) | 0.73254 (12) | 0.18488 (10) | 0.0358 (5) | |
H11D | 0.606774 | 0.723634 | 0.153544 | 0.043* | |
C12D | 0.5375 (2) | 0.67071 (12) | 0.23253 (10) | 0.0363 (5) | |
C13D | 0.5449 (3) | 0.60356 (14) | 0.22646 (12) | 0.0479 (6) | |
H13D | 0.567937 | 0.599002 | 0.191540 | 0.058* | |
C14D | 0.5193 (3) | 0.54365 (14) | 0.27040 (12) | 0.0489 (7) | |
H14D | 0.524588 | 0.499738 | 0.264807 | 0.059* | |
C15D | 0.4856 (3) | 0.54910 (13) | 0.32285 (11) | 0.0409 (6) | |
C16D | 0.4824 (2) | 0.61498 (13) | 0.33092 (11) | 0.0386 (5) | |
H16D | 0.463280 | 0.618790 | 0.366341 | 0.046* | |
C17D | 0.5073 (2) | 0.67434 (12) | 0.28650 (11) | 0.0354 (5) | |
H17D | 0.504116 | 0.717948 | 0.292432 | 0.043* | |
C18D | 0.8177 (2) | 0.88359 (15) | 0.02564 (13) | 0.0453 (6) | |
C26D | 0.0331 (3) | 1.22342 (15) | 0.18465 (15) | 0.0539 (7) | |
H26J | 0.009561 | 1.270676 | 0.186504 | 0.081* | |
H26K | 0.014110 | 1.188981 | 0.220161 | 0.081* | |
H26L | −0.017203 | 1.217610 | 0.155763 | 0.081* | |
C27D | 0.4637 (3) | 0.42460 (14) | 0.36333 (13) | 0.0554 (7) | |
H27J | 0.436668 | 0.391242 | 0.397991 | 0.083* | |
H27K | 0.552803 | 0.409205 | 0.354291 | 0.083* | |
H27L | 0.405868 | 0.427030 | 0.333790 | 0.083* | |
C1B | −0.1596 (13) | 1.0124 (6) | 0.2057 (4) | 0.029 (2) | 0.667 (7) |
H1BA | −0.139365 | 0.976700 | 0.239899 | 0.035* | 0.667 (7) |
C2B | −0.2170 (17) | 1.0787 (6) | 0.2066 (4) | 0.030 (2) | 0.667 (7) |
H2BA | −0.231049 | 1.088033 | 0.240317 | 0.036* | 0.667 (7) |
C3B | −0.2530 (12) | 1.1308 (4) | 0.1560 (3) | 0.0299 (19) | 0.667 (7) |
C4B | −0.2285 (12) | 1.1158 (4) | 0.1058 (3) | 0.0291 (17) | 0.667 (7) |
H4BA | −0.253074 | 1.150920 | 0.071809 | 0.035* | 0.667 (7) |
C5B | −0.1684 (9) | 1.0497 (5) | 0.1060 (4) | 0.0258 (17) | 0.667 (7) |
H5BA | −0.153061 | 1.040639 | 0.072191 | 0.031* | 0.667 (7) |
C6B | −0.1304 (8) | 0.9961 (5) | 0.1564 (3) | 0.0209 (16) | 0.667 (7) |
C7B | −0.0605 (7) | 0.9261 (4) | 0.1610 (3) | 0.0268 (14) | 0.667 (7) |
H7BA | −0.060254 | 0.890582 | 0.195945 | 0.032* | 0.667 (7) |
C8B | 0.0037 (6) | 0.9091 (4) | 0.1185 (2) | 0.0276 (12) | 0.667 (7) |
H8BA | 0.002944 | 0.942997 | 0.082753 | 0.033* | 0.667 (7) |
N1B | 0.1817 (5) | 0.8225 (2) | 0.10207 (19) | 0.0291 (10) | 0.667 (7) |
C9B | 0.0749 (6) | 0.8374 (3) | 0.12805 (19) | 0.0269 (10) | 0.667 (7) |
C10B | 0.0237 (4) | 0.77673 (17) | 0.17134 (15) | 0.0293 (10) | 0.667 (7) |
H10B | −0.067534 | 0.776853 | 0.174888 | 0.035* | 0.667 (7) |
C11B | 0.0995 (4) | 0.7220 (2) | 0.20555 (17) | 0.0310 (10) | 0.667 (7) |
H11B | 0.190427 | 0.723056 | 0.201807 | 0.037* | 0.667 (7) |
C12B | 0.0539 (6) | 0.6597 (2) | 0.24877 (17) | 0.0291 (10) | 0.667 (7) |
C13B | 0.1395 (5) | 0.6162 (3) | 0.2913 (2) | 0.0331 (11) | 0.667 (7) |
H13B | 0.224929 | 0.627323 | 0.291609 | 0.040* | 0.667 (7) |
C14B | 0.1013 (8) | 0.5567 (4) | 0.3331 (4) | 0.0309 (17) | 0.667 (7) |
H14B | 0.159726 | 0.528900 | 0.361364 | 0.037* | 0.667 (7) |
C15B | −0.0261 (14) | 0.5392 (7) | 0.3321 (7) | 0.0276 (18) | 0.667 (7) |
C16B | −0.1120 (6) | 0.5806 (4) | 0.2896 (3) | 0.0311 (15) | 0.667 (7) |
H16B | −0.195961 | 0.568073 | 0.288374 | 0.037* | 0.667 (7) |
C17B | −0.0728 (6) | 0.6407 (3) | 0.2489 (2) | 0.0304 (10) | 0.667 (7) |
H17B | −0.132224 | 0.668952 | 0.221220 | 0.036* | 0.667 (7) |
C1X | −0.139 (3) | 0.9949 (10) | 0.2158 (6) | 0.021 (3) | 0.333 (7) |
H1XB | −0.111834 | 0.963916 | 0.251090 | 0.025* | 0.333 (7) |
C2X | −0.212 (4) | 1.0607 (11) | 0.2108 (9) | 0.029 (4) | 0.333 (7) |
H2XB | −0.233806 | 1.072327 | 0.243153 | 0.035* | 0.333 (7) |
C3X | −0.253 (2) | 1.1094 (8) | 0.1593 (8) | 0.029 (4) | 0.333 (7) |
C4X | −0.221 (2) | 1.0902 (8) | 0.1111 (6) | 0.026 (4) | 0.333 (7) |
H4XB | −0.247986 | 1.121596 | 0.075905 | 0.031* | 0.333 (7) |
C5X | −0.1507 (19) | 1.0247 (8) | 0.1159 (7) | 0.026 (4) | 0.333 (7) |
H5XB | −0.131880 | 1.012595 | 0.083493 | 0.032* | 0.333 (7) |
C6X | −0.1057 (17) | 0.9753 (8) | 0.1680 (7) | 0.023 (4) | 0.333 (7) |
C7X | −0.0213 (13) | 0.9091 (8) | 0.1718 (6) | 0.030 (3) | 0.333 (7) |
H7XB | −0.010847 | 0.875995 | 0.207777 | 0.036* | 0.333 (7) |
C8X | 0.0432 (11) | 0.8893 (6) | 0.1309 (4) | 0.022 (2) | 0.333 (7) |
H8XB | 0.029093 | 0.918740 | 0.093893 | 0.027* | 0.333 (7) |
N1X | 0.2384 (10) | 0.8148 (5) | 0.1119 (4) | 0.0275 (19) | 0.333 (7) |
C9X | 0.1350 (11) | 0.8235 (4) | 0.1415 (4) | 0.0262 (19) | 0.333 (7) |
C10X | 0.1172 (8) | 0.7579 (5) | 0.1892 (3) | 0.030 (2) | 0.333 (7) |
H10E | 0.192881 | 0.727915 | 0.205173 | 0.036* | 0.333 (7) |
C11X | 0.0016 (7) | 0.7388 (3) | 0.2107 (3) | 0.032 (2) | 0.333 (7) |
H11E | −0.073871 | 0.770751 | 0.197430 | 0.039* | 0.333 (7) |
C12X | −0.0153 (12) | 0.6696 (4) | 0.2549 (3) | 0.0274 (18) | 0.333 (7) |
C13X | 0.0832 (11) | 0.6316 (5) | 0.2930 (4) | 0.031 (2) | 0.333 (7) |
H13E | 0.162299 | 0.649756 | 0.293077 | 0.038* | 0.333 (7) |
C14X | 0.0608 (17) | 0.5656 (9) | 0.3311 (9) | 0.040 (5) | 0.333 (7) |
H14E | 0.126458 | 0.540056 | 0.356782 | 0.048* | 0.333 (7) |
C15X | −0.055 (3) | 0.5364 (16) | 0.3323 (16) | 0.039 (6) | 0.333 (7) |
C16X | −0.1558 (12) | 0.5768 (7) | 0.2966 (7) | 0.028 (3) | 0.333 (7) |
H16E | −0.237504 | 0.560458 | 0.298540 | 0.033* | 0.333 (7) |
C17X | −0.1335 (12) | 0.6423 (5) | 0.2579 (4) | 0.034 (2) | 0.333 (7) |
H17E | −0.200591 | 0.668545 | 0.233116 | 0.040* | 0.333 (7) |
S1D | 0.8699 (3) | 0.79428 (15) | 0.04235 (14) | 0.0365 (7) | 0.653 (15) |
C19D | 0.9873 (8) | 0.7925 (4) | −0.0153 (4) | 0.051 (2) | 0.653 (15) |
H19I | 0.950782 | 0.825342 | −0.050551 | 0.061* | 0.653 (15) |
H19J | 1.069360 | 0.808008 | −0.008995 | 0.061* | 0.653 (15) |
C20D | 1.0154 (10) | 0.7177 (4) | −0.0193 (5) | 0.044 (4) | 0.653 (15) |
C21D | 1.1364 (9) | 0.6760 (6) | −0.0038 (8) | 0.061 (4) | 0.653 (15) |
H21E | 1.200316 | 0.692883 | 0.011566 | 0.073* | 0.653 (15) |
C22D | 1.1633 (10) | 0.6110 (5) | −0.0105 (6) | 0.085 (4) | 0.653 (15) |
H22E | 1.246292 | 0.584690 | −0.001506 | 0.102* | 0.653 (15) |
C23D | 1.0684 (8) | 0.5845 (4) | −0.0306 (5) | 0.074 (3) | 0.653 (15) |
H23E | 1.087546 | 0.539982 | −0.035108 | 0.088* | 0.653 (15) |
C24D | 0.9478 (9) | 0.6212 (6) | −0.0441 (5) | 0.071 (3) | 0.653 (15) |
H24E | 0.883543 | 0.602240 | −0.057484 | 0.085* | 0.653 (15) |
C25D | 0.9208 (10) | 0.6879 (6) | −0.0376 (7) | 0.054 (3) | 0.653 (15) |
H25E | 0.836706 | 0.713090 | −0.045780 | 0.065* | 0.653 (15) |
S1Y | 0.8920 (8) | 0.7789 (5) | 0.0574 (5) | 0.0813 (19) | 0.347 (15) |
C19Y | 1.0241 (12) | 0.7814 (8) | 0.0076 (8) | 0.054 (4) | 0.347 (15) |
H19G | 1.013928 | 0.826836 | −0.022623 | 0.065* | 0.347 (15) |
H19H | 1.108093 | 0.776286 | 0.025658 | 0.065* | 0.347 (15) |
C20Y | 1.0216 (16) | 0.7214 (10) | −0.0157 (9) | 0.044 (8) | 0.347 (15) |
C21Y | 1.1406 (16) | 0.6813 (10) | −0.0196 (13) | 0.056 (6) | 0.347 (15) |
H21D | 1.217987 | 0.693653 | −0.009528 | 0.067* | 0.347 (15) |
C22Y | 1.1474 (18) | 0.6241 (9) | −0.0378 (9) | 0.077 (6) | 0.347 (15) |
H22D | 1.226880 | 0.594744 | −0.036620 | 0.092* | 0.347 (15) |
C23Y | 1.036 (2) | 0.6105 (11) | −0.0579 (9) | 0.090 (7) | 0.347 (15) |
H23D | 1.038945 | 0.571969 | −0.070840 | 0.109* | 0.347 (15) |
C24Y | 0.9215 (19) | 0.6529 (12) | −0.0588 (9) | 0.068 (5) | 0.347 (15) |
H24D | 0.845672 | 0.642475 | −0.071739 | 0.082* | 0.347 (15) |
C25Y | 0.913 (2) | 0.7121 (10) | −0.0411 (12) | 0.051 (4) | 0.347 (15) |
H25D | 0.836440 | 0.744372 | −0.046356 | 0.061* | 0.347 (15) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1A | 0.0301 (3) | 0.0200 (2) | 0.0393 (3) | −0.00488 (19) | 0.0081 (2) | −0.0098 (2) |
S2A | 0.0309 (3) | 0.0217 (2) | 0.0313 (3) | −0.00635 (19) | 0.0073 (2) | −0.0069 (2) |
N1A | 0.0334 (9) | 0.0227 (8) | 0.0307 (10) | −0.0076 (7) | 0.0069 (8) | −0.0084 (7) |
N2A | 0.0315 (9) | 0.0186 (9) | 0.0308 (10) | −0.0053 (7) | 0.0080 (8) | −0.0071 (7) |
O1A | 0.0435 (10) | 0.0347 (9) | 0.0599 (12) | 0.0027 (7) | 0.0104 (9) | −0.0222 (8) |
O2A | 0.0482 (10) | 0.0340 (9) | 0.0518 (12) | −0.0091 (8) | −0.0051 (9) | 0.0102 (8) |
C1A | 0.0329 (11) | 0.0358 (12) | 0.0340 (12) | −0.0105 (9) | 0.0066 (9) | −0.0164 (10) |
C2A | 0.0289 (11) | 0.0418 (13) | 0.0427 (14) | −0.0057 (9) | 0.0079 (10) | −0.0220 (11) |
C3A | 0.0355 (12) | 0.0335 (12) | 0.0360 (13) | 0.0008 (9) | 0.0002 (10) | −0.0160 (10) |
C4A | 0.0425 (13) | 0.0291 (11) | 0.0336 (13) | −0.0061 (9) | 0.0085 (10) | −0.0096 (10) |
C5A | 0.0345 (11) | 0.0310 (11) | 0.0292 (12) | −0.0043 (9) | 0.0079 (9) | −0.0114 (9) |
C6A | 0.0308 (11) | 0.0302 (11) | 0.0236 (11) | −0.0048 (8) | 0.0012 (9) | −0.0115 (9) |
C7A | 0.0345 (11) | 0.0278 (11) | 0.0247 (11) | −0.0080 (9) | 0.0037 (9) | −0.0105 (9) |
C8A | 0.0357 (11) | 0.0243 (10) | 0.0255 (11) | −0.0065 (8) | 0.0054 (9) | −0.0066 (9) |
C9A | 0.0334 (11) | 0.0264 (10) | 0.0248 (11) | −0.0044 (8) | 0.0031 (9) | −0.0091 (9) |
C10A | 0.0355 (11) | 0.0252 (10) | 0.0288 (11) | −0.0063 (9) | 0.0078 (9) | −0.0088 (9) |
C11A | 0.0356 (12) | 0.0279 (11) | 0.0344 (12) | −0.0074 (9) | 0.0069 (10) | −0.0100 (9) |
C12A | 0.0370 (12) | 0.0236 (10) | 0.0344 (12) | −0.0033 (9) | 0.0035 (10) | −0.0089 (9) |
C13A | 0.0355 (12) | 0.0296 (11) | 0.0458 (15) | −0.0045 (9) | −0.0003 (11) | −0.0102 (10) |
C14A | 0.0423 (13) | 0.0287 (12) | 0.0438 (15) | 0.0006 (10) | −0.0083 (11) | −0.0043 (10) |
C15A | 0.0448 (13) | 0.0235 (11) | 0.0390 (14) | −0.0051 (9) | 0.0014 (11) | −0.0015 (10) |
C16A | 0.0364 (12) | 0.0304 (12) | 0.0414 (14) | −0.0062 (9) | −0.0001 (10) | −0.0056 (10) |
C17A | 0.0369 (12) | 0.0258 (11) | 0.0335 (12) | −0.0035 (9) | −0.0018 (10) | −0.0036 (9) |
C18A | 0.0306 (11) | 0.0233 (10) | 0.0258 (11) | −0.0038 (8) | 0.0009 (9) | −0.0090 (8) |
C19A | 0.0344 (12) | 0.0324 (12) | 0.0737 (19) | −0.0117 (10) | 0.0225 (12) | −0.0260 (13) |
C20A | 0.0254 (10) | 0.0238 (10) | 0.0436 (13) | −0.0058 (8) | 0.0105 (9) | −0.0119 (9) |
C21A | 0.0333 (12) | 0.0342 (12) | 0.0445 (15) | 0.0024 (9) | −0.0027 (11) | −0.0050 (11) |
C22A | 0.0421 (13) | 0.0490 (15) | 0.0387 (14) | −0.0095 (11) | −0.0008 (11) | −0.0183 (12) |
C23A | 0.0412 (13) | 0.0300 (12) | 0.0452 (14) | −0.0088 (10) | 0.0116 (11) | −0.0193 (11) |
C24A | 0.0448 (13) | 0.0256 (11) | 0.0402 (14) | 0.0024 (10) | 0.0022 (11) | −0.0064 (10) |
C25A | 0.0358 (12) | 0.0361 (12) | 0.0320 (12) | −0.0030 (9) | 0.0021 (10) | −0.0138 (10) |
C26A | 0.0396 (15) | 0.0581 (18) | 0.103 (3) | −0.0019 (13) | 0.0169 (16) | −0.0499 (19) |
C27A | 0.0535 (17) | 0.0412 (15) | 0.0609 (19) | −0.0163 (12) | −0.0006 (14) | 0.0159 (13) |
S1B | 0.0543 (3) | 0.0217 (3) | 0.0302 (3) | −0.0108 (2) | 0.0017 (3) | −0.0054 (2) |
S2B | 0.0332 (3) | 0.0219 (2) | 0.0328 (3) | −0.0084 (2) | −0.0018 (2) | −0.0040 (2) |
N2B | 0.0628 (14) | 0.0239 (10) | 0.0314 (11) | −0.0189 (9) | 0.0156 (10) | −0.0112 (8) |
O1B | 0.0473 (11) | 0.0752 (14) | 0.0357 (10) | 0.0109 (10) | −0.0045 (8) | −0.0181 (9) |
O2B | 0.0474 (10) | 0.0287 (8) | 0.0323 (9) | −0.0060 (7) | −0.0001 (7) | −0.0015 (7) |
C18B | 0.0459 (13) | 0.0242 (10) | 0.0245 (11) | −0.0113 (9) | −0.0045 (10) | −0.0072 (9) |
C19B | 0.0366 (13) | 0.0252 (12) | 0.0653 (18) | −0.0047 (9) | 0.0082 (12) | −0.0087 (11) |
C20B | 0.0368 (12) | 0.0258 (11) | 0.0392 (13) | −0.0058 (9) | 0.0057 (10) | −0.0032 (10) |
C21B | 0.0485 (15) | 0.0496 (15) | 0.0412 (15) | −0.0040 (12) | 0.0010 (12) | −0.0063 (12) |
C22B | 0.0634 (19) | 0.073 (2) | 0.0441 (17) | −0.0195 (16) | 0.0089 (14) | −0.0273 (15) |
C23B | 0.075 (2) | 0.0416 (15) | 0.0479 (17) | −0.0237 (14) | 0.0275 (15) | −0.0219 (13) |
C24B | 0.0726 (19) | 0.0271 (12) | 0.0473 (16) | 0.0031 (12) | 0.0079 (14) | −0.0067 (11) |
C25B | 0.0520 (15) | 0.0334 (13) | 0.0436 (15) | 0.0029 (11) | −0.0059 (12) | −0.0111 (11) |
C26B | 0.0617 (18) | 0.070 (2) | 0.0434 (17) | 0.0083 (15) | −0.0038 (14) | −0.0234 (15) |
C27B | 0.0524 (15) | 0.0433 (14) | 0.0417 (15) | −0.0127 (12) | 0.0022 (12) | −0.0095 (12) |
S1C | 0.0381 (3) | 0.0262 (3) | 0.0332 (3) | −0.0085 (2) | 0.0095 (2) | −0.0076 (2) |
S2C | 0.0535 (4) | 0.0247 (3) | 0.0479 (4) | −0.0063 (2) | 0.0203 (3) | −0.0055 (3) |
N1C | 0.0368 (10) | 0.0285 (9) | 0.0274 (10) | −0.0124 (8) | 0.0036 (8) | −0.0062 (8) |
N2C | 0.0369 (10) | 0.0225 (9) | 0.0307 (10) | −0.0068 (7) | 0.0037 (8) | −0.0051 (8) |
O1C | 0.0427 (9) | 0.0333 (9) | 0.0479 (11) | −0.0034 (7) | 0.0099 (8) | −0.0113 (8) |
O2C | 0.0723 (14) | 0.0424 (11) | 0.0485 (12) | −0.0232 (10) | 0.0037 (10) | 0.0108 (9) |
C1C | 0.0398 (13) | 0.0328 (12) | 0.0324 (13) | −0.0032 (10) | 0.0070 (10) | 0.0007 (10) |
C2C | 0.0378 (12) | 0.0419 (13) | 0.0269 (12) | −0.0038 (10) | 0.0039 (10) | −0.0047 (10) |
C3C | 0.0304 (11) | 0.0306 (11) | 0.0341 (12) | −0.0024 (9) | −0.0026 (9) | −0.0081 (9) |
C4C | 0.0413 (13) | 0.0323 (12) | 0.0354 (13) | −0.0034 (10) | 0.0087 (11) | 0.0022 (10) |
C5C | 0.0380 (12) | 0.0365 (12) | 0.0293 (12) | −0.0009 (10) | 0.0068 (10) | −0.0014 (10) |
C6C | 0.0299 (11) | 0.0331 (11) | 0.0290 (12) | −0.0068 (9) | 0.0004 (9) | −0.0056 (9) |
C7C | 0.0364 (12) | 0.0270 (11) | 0.0339 (12) | −0.0079 (9) | 0.0025 (10) | −0.0032 (9) |
C8C | 0.0389 (12) | 0.0277 (11) | 0.0235 (11) | −0.0112 (9) | 0.0031 (9) | −0.0039 (9) |
C9C | 0.0327 (11) | 0.0291 (11) | 0.0280 (11) | −0.0077 (9) | 0.0017 (9) | −0.0092 (9) |
C10C | 0.0339 (11) | 0.0321 (12) | 0.0265 (11) | −0.0062 (9) | 0.0078 (9) | −0.0063 (9) |
C11C | 0.0356 (12) | 0.0317 (12) | 0.0271 (12) | −0.0077 (9) | 0.0042 (9) | −0.0071 (9) |
C12C | 0.0311 (11) | 0.0310 (11) | 0.0316 (12) | −0.0081 (9) | 0.0002 (9) | −0.0052 (9) |
C13C | 0.0532 (15) | 0.0320 (12) | 0.0350 (13) | −0.0111 (11) | −0.0006 (11) | −0.0093 (10) |
C14C | 0.0563 (16) | 0.0306 (12) | 0.0463 (16) | −0.0123 (11) | −0.0056 (12) | −0.0066 (11) |
C15C | 0.0431 (14) | 0.0374 (13) | 0.0394 (14) | −0.0152 (11) | −0.0012 (11) | 0.0034 (11) |
C16C | 0.0387 (13) | 0.0445 (14) | 0.0328 (13) | −0.0083 (10) | 0.0061 (10) | −0.0030 (11) |
C17C | 0.0333 (11) | 0.0330 (12) | 0.0331 (13) | −0.0055 (9) | 0.0036 (10) | −0.0065 (10) |
C18C | 0.0307 (11) | 0.0403 (13) | 0.0373 (13) | −0.0051 (9) | −0.0026 (10) | −0.0196 (10) |
C19C | 0.0370 (12) | 0.0304 (11) | 0.0377 (13) | −0.0084 (9) | 0.0116 (10) | −0.0090 (10) |
C20C | 0.0329 (11) | 0.0272 (11) | 0.0285 (11) | −0.0073 (9) | 0.0076 (9) | −0.0057 (9) |
C21C | 0.0338 (12) | 0.0352 (13) | 0.0499 (15) | −0.0066 (10) | −0.0005 (11) | −0.0106 (11) |
C22C | 0.0405 (14) | 0.0351 (14) | 0.072 (2) | 0.0016 (11) | 0.0072 (13) | −0.0111 (13) |
C23C | 0.0533 (16) | 0.0315 (13) | 0.0578 (17) | −0.0107 (11) | 0.0216 (13) | −0.0182 (12) |
C24C | 0.0499 (15) | 0.0432 (14) | 0.0460 (15) | −0.0161 (11) | 0.0081 (12) | −0.0226 (12) |
C25C | 0.0337 (12) | 0.0391 (13) | 0.0386 (14) | −0.0047 (10) | 0.0020 (10) | −0.0106 (11) |
C26C | 0.0379 (13) | 0.0456 (14) | 0.0449 (15) | −0.0023 (11) | 0.0025 (11) | −0.0192 (12) |
C27C | 0.105 (3) | 0.0408 (17) | 0.071 (2) | −0.0374 (18) | −0.011 (2) | 0.0111 (15) |
S2D | 0.0492 (4) | 0.0477 (4) | 0.0563 (4) | −0.0066 (3) | 0.0186 (3) | −0.0207 (3) |
N1D | 0.0320 (10) | 0.0413 (11) | 0.0354 (11) | −0.0110 (8) | −0.0014 (8) | −0.0079 (9) |
N2D | 0.0332 (10) | 0.0341 (11) | 0.0376 (11) | −0.0052 (8) | 0.0027 (8) | −0.0106 (9) |
O1D | 0.0450 (10) | 0.0380 (9) | 0.0616 (12) | −0.0128 (8) | 0.0166 (9) | −0.0233 (9) |
O2D | 0.0618 (12) | 0.0322 (9) | 0.0441 (11) | −0.0108 (8) | 0.0040 (9) | −0.0033 (8) |
C1D | 0.0349 (12) | 0.0310 (12) | 0.0423 (14) | −0.0131 (9) | 0.0062 (10) | −0.0098 (10) |
C2D | 0.0347 (12) | 0.0392 (13) | 0.0432 (14) | −0.0128 (10) | 0.0095 (11) | −0.0124 (11) |
C3D | 0.0416 (13) | 0.0306 (11) | 0.0343 (13) | −0.0102 (10) | 0.0081 (10) | −0.0109 (10) |
C4D | 0.0401 (13) | 0.0372 (13) | 0.0425 (14) | −0.0190 (10) | 0.0108 (11) | −0.0129 (11) |
C5D | 0.0349 (12) | 0.0365 (12) | 0.0361 (13) | −0.0130 (10) | 0.0101 (10) | −0.0098 (10) |
C6D | 0.0341 (11) | 0.0335 (11) | 0.0232 (11) | −0.0119 (9) | 0.0021 (9) | −0.0045 (9) |
C7D | 0.0321 (11) | 0.0299 (11) | 0.0253 (11) | −0.0101 (9) | 0.0016 (9) | −0.0044 (9) |
C8D | 0.0339 (11) | 0.0347 (12) | 0.0224 (11) | −0.0112 (9) | 0.0008 (9) | −0.0039 (9) |
C9D | 0.0268 (11) | 0.0372 (12) | 0.0291 (12) | −0.0045 (9) | −0.0015 (9) | −0.0107 (10) |
C10D | 0.0300 (11) | 0.0374 (12) | 0.0298 (12) | −0.0061 (9) | −0.0007 (9) | −0.0069 (10) |
C11D | 0.0400 (13) | 0.0374 (12) | 0.0301 (12) | −0.0033 (10) | −0.0059 (10) | −0.0109 (10) |
C12D | 0.0401 (13) | 0.0345 (12) | 0.0321 (13) | −0.0044 (10) | −0.0061 (10) | −0.0071 (10) |
C13D | 0.0727 (19) | 0.0376 (13) | 0.0355 (14) | −0.0083 (12) | −0.0067 (13) | −0.0132 (11) |
C14D | 0.0716 (19) | 0.0338 (13) | 0.0421 (15) | −0.0105 (12) | −0.0076 (13) | −0.0111 (11) |
C15D | 0.0424 (13) | 0.0351 (13) | 0.0419 (14) | −0.0062 (10) | −0.0050 (11) | −0.0072 (11) |
C16D | 0.0382 (13) | 0.0396 (13) | 0.0360 (13) | −0.0058 (10) | 0.0048 (10) | −0.0101 (11) |
C17D | 0.0334 (12) | 0.0319 (12) | 0.0401 (13) | −0.0034 (9) | 0.0005 (10) | −0.0111 (10) |
C18D | 0.0307 (12) | 0.0566 (16) | 0.0632 (18) | 0.0055 (11) | −0.0055 (12) | −0.0428 (14) |
C26D | 0.0476 (15) | 0.0446 (15) | 0.073 (2) | −0.0082 (12) | 0.0203 (14) | −0.0268 (14) |
C27D | 0.073 (2) | 0.0348 (14) | 0.0557 (18) | −0.0164 (13) | −0.0096 (15) | −0.0062 (12) |
C1B | 0.034 (4) | 0.028 (5) | 0.017 (3) | −0.006 (3) | −0.003 (3) | 0.003 (3) |
C2B | 0.031 (3) | 0.036 (6) | 0.028 (4) | −0.006 (5) | 0.003 (3) | −0.017 (4) |
C3B | 0.031 (3) | 0.038 (5) | 0.026 (3) | −0.013 (4) | 0.0024 (18) | −0.013 (3) |
C4B | 0.029 (2) | 0.029 (4) | 0.028 (3) | −0.005 (4) | 0.0014 (18) | −0.007 (3) |
C5B | 0.025 (3) | 0.032 (5) | 0.018 (3) | −0.004 (4) | 0.001 (2) | −0.005 (3) |
C6B | 0.023 (3) | 0.023 (4) | 0.014 (4) | −0.005 (2) | −0.002 (3) | −0.001 (3) |
C7B | 0.026 (3) | 0.028 (4) | 0.027 (3) | −0.010 (2) | 0.006 (2) | −0.008 (2) |
C8B | 0.032 (3) | 0.024 (3) | 0.026 (3) | −0.007 (2) | −0.0022 (19) | −0.006 (2) |
N1B | 0.034 (2) | 0.0267 (18) | 0.028 (2) | −0.0109 (19) | 0.0058 (19) | −0.0091 (15) |
C9B | 0.028 (2) | 0.028 (2) | 0.029 (2) | −0.009 (2) | 0.0063 (18) | −0.0129 (17) |
C10B | 0.034 (2) | 0.0270 (18) | 0.029 (2) | −0.0110 (15) | 0.0112 (16) | −0.0103 (16) |
C11B | 0.032 (2) | 0.026 (2) | 0.037 (2) | −0.0098 (19) | 0.0076 (16) | −0.0130 (19) |
C12B | 0.031 (3) | 0.0264 (19) | 0.031 (2) | −0.0069 (18) | 0.0028 (19) | −0.0100 (17) |
C13B | 0.029 (3) | 0.032 (2) | 0.040 (2) | −0.004 (2) | 0.000 (2) | −0.0135 (18) |
C14B | 0.032 (4) | 0.026 (3) | 0.034 (3) | −0.004 (3) | −0.009 (3) | −0.007 (2) |
C15B | 0.036 (5) | 0.020 (3) | 0.026 (3) | −0.007 (3) | −0.005 (3) | −0.005 (2) |
C16B | 0.025 (3) | 0.035 (3) | 0.035 (3) | −0.011 (2) | 0.003 (3) | −0.012 (2) |
C17B | 0.031 (3) | 0.027 (2) | 0.030 (2) | −0.005 (2) | −0.003 (2) | −0.0031 (16) |
C1X | 0.028 (7) | 0.021 (8) | 0.009 (5) | 0.000 (5) | −0.003 (4) | 0.000 (5) |
C2X | 0.047 (8) | 0.016 (9) | 0.022 (6) | −0.011 (7) | 0.003 (4) | −0.001 (4) |
C3X | 0.019 (4) | 0.019 (7) | 0.053 (8) | −0.005 (5) | 0.004 (4) | −0.017 (5) |
C4X | 0.031 (6) | 0.027 (10) | 0.021 (5) | −0.011 (9) | −0.001 (4) | −0.005 (6) |
C5X | 0.027 (6) | 0.019 (8) | 0.028 (9) | −0.001 (6) | −0.004 (5) | −0.003 (7) |
C6X | 0.027 (7) | 0.018 (8) | 0.014 (6) | −0.006 (5) | −0.010 (4) | 0.011 (5) |
C7X | 0.030 (7) | 0.025 (6) | 0.044 (7) | −0.007 (4) | −0.001 (5) | −0.020 (5) |
C8X | 0.025 (6) | 0.022 (7) | 0.016 (5) | −0.010 (4) | 0.004 (4) | 0.001 (4) |
N1X | 0.032 (5) | 0.023 (3) | 0.030 (4) | −0.009 (4) | 0.008 (4) | −0.012 (3) |
C9X | 0.027 (5) | 0.025 (4) | 0.033 (5) | −0.010 (4) | 0.006 (4) | −0.017 (3) |
C10X | 0.032 (5) | 0.027 (5) | 0.035 (5) | −0.002 (3) | 0.000 (3) | −0.014 (4) |
C11X | 0.035 (5) | 0.027 (4) | 0.035 (5) | 0.003 (3) | 0.001 (3) | −0.013 (3) |
C12X | 0.031 (5) | 0.026 (4) | 0.026 (4) | −0.008 (4) | 0.010 (4) | −0.010 (3) |
C13X | 0.034 (6) | 0.025 (5) | 0.037 (5) | −0.011 (4) | 0.007 (5) | −0.011 (4) |
C14X | 0.043 (11) | 0.041 (7) | 0.028 (5) | 0.010 (7) | −0.018 (7) | −0.006 (4) |
C15X | 0.047 (12) | 0.034 (8) | 0.044 (9) | −0.015 (7) | 0.007 (8) | −0.020 (7) |
C16X | 0.028 (6) | 0.015 (4) | 0.034 (5) | −0.006 (4) | 0.008 (5) | 0.000 (3) |
C17X | 0.034 (6) | 0.028 (4) | 0.036 (5) | 0.000 (4) | 0.002 (4) | −0.008 (3) |
S1D | 0.0330 (8) | 0.0158 (8) | 0.0538 (12) | 0.0001 (6) | 0.0177 (7) | −0.0066 (7) |
C19D | 0.046 (4) | 0.040 (3) | 0.061 (4) | −0.007 (3) | 0.028 (3) | −0.012 (3) |
C20D | 0.041 (7) | 0.025 (4) | 0.055 (6) | 0.000 (4) | 0.004 (4) | −0.001 (4) |
C21D | 0.043 (4) | 0.054 (5) | 0.088 (10) | 0.013 (4) | −0.018 (4) | −0.034 (6) |
C22D | 0.057 (4) | 0.044 (4) | 0.149 (11) | 0.006 (3) | −0.009 (5) | −0.029 (5) |
C23D | 0.070 (4) | 0.052 (4) | 0.110 (7) | −0.029 (3) | 0.043 (5) | −0.039 (4) |
C24D | 0.071 (6) | 0.087 (7) | 0.069 (6) | −0.054 (5) | 0.016 (4) | −0.030 (5) |
C25D | 0.036 (3) | 0.046 (6) | 0.066 (5) | −0.007 (4) | −0.001 (3) | 0.001 (6) |
S1Y | 0.040 (2) | 0.055 (3) | 0.114 (4) | −0.0129 (18) | 0.018 (2) | 0.020 (3) |
C19Y | 0.028 (5) | 0.041 (6) | 0.098 (12) | −0.013 (4) | 0.019 (6) | −0.030 (8) |
C20Y | 0.029 (11) | 0.061 (13) | 0.053 (11) | −0.025 (8) | 0.028 (8) | −0.032 (9) |
C21Y | 0.050 (8) | 0.041 (7) | 0.075 (14) | −0.031 (7) | −0.004 (6) | −0.006 (6) |
C22Y | 0.070 (9) | 0.039 (7) | 0.120 (16) | 0.013 (6) | −0.013 (9) | −0.030 (9) |
C23Y | 0.133 (19) | 0.078 (12) | 0.088 (13) | −0.067 (13) | 0.035 (12) | −0.048 (10) |
C24Y | 0.082 (10) | 0.080 (13) | 0.059 (10) | −0.054 (10) | 0.020 (7) | −0.028 (10) |
C25Y | 0.043 (7) | 0.041 (10) | 0.055 (7) | −0.007 (6) | −0.007 (5) | 0.003 (9) |
S1A—C18A | 1.760 (2) | C24C—H24C | 0.9300 |
S1A—C19A | 1.814 (2) | C25C—H25C | 0.9300 |
S2A—C18A | 1.661 (2) | C26C—H26G | 0.9600 |
N1A—C9A | 1.298 (3) | C26C—H26H | 0.9600 |
N1A—N2A | 1.371 (3) | C26C—H26I | 0.9600 |
N2A—C18A | 1.344 (3) | C27C—H27G | 0.9600 |
N2A—H1N2 | 0.81 (3) | C27C—H27H | 0.9600 |
O1A—C3A | 1.367 (3) | C27C—H27I | 0.9600 |
O1A—C26A | 1.414 (3) | S2D—C18D | 1.621 (3) |
O2A—C15A | 1.369 (3) | N1D—C9D | 1.317 (3) |
O2A—C27A | 1.435 (3) | N1D—N2D | 1.354 (3) |
C1A—C6A | 1.384 (3) | N2D—C18D | 1.367 (3) |
C1A—C2A | 1.391 (3) | N2D—H4N2 | 0.91 (4) |
C1A—H1AA | 0.9300 | O1D—C3D | 1.367 (3) |
C2A—C3A | 1.386 (3) | O1D—C26D | 1.428 (3) |
C2A—H2AA | 0.9300 | O2D—C15D | 1.366 (3) |
C3A—C4A | 1.389 (3) | O2D—C27D | 1.434 (3) |
C4A—C5A | 1.375 (3) | C1D—C2D | 1.382 (3) |
C4A—H4AA | 0.9300 | C1D—C6D | 1.393 (3) |
C5A—C6A | 1.405 (3) | C1D—H1DA | 0.9300 |
C5A—H5AA | 0.9300 | C2D—C3D | 1.391 (3) |
C6A—C7A | 1.464 (3) | C2D—H2DA | 0.9300 |
C7A—C8A | 1.332 (3) | C3D—C4D | 1.391 (3) |
C7A—H7AA | 0.9300 | C4D—C5D | 1.373 (3) |
C8A—C9A | 1.462 (3) | C4D—H4DA | 0.9300 |
C8A—H8AA | 0.9300 | C5D—C6D | 1.402 (3) |
C9A—C10A | 1.476 (3) | C5D—H5DA | 0.9300 |
C10A—C11A | 1.337 (3) | C6D—C7D | 1.458 (3) |
C10A—H10A | 0.9300 | C7D—C8D | 1.340 (3) |
C11A—C12A | 1.467 (3) | C7D—H7DA | 0.9300 |
C11A—H11A | 0.9300 | C8D—C9D | 1.463 (3) |
C12A—C17A | 1.397 (3) | C8D—H8DA | 0.9300 |
C12A—C13A | 1.398 (3) | C9D—C10D | 1.471 (3) |
C13A—C14A | 1.380 (3) | C10D—C11D | 1.337 (3) |
C13A—H13A | 0.9300 | C10D—H10D | 0.9300 |
C14A—C15A | 1.392 (4) | C11D—C12D | 1.461 (3) |
C14A—H14A | 0.9300 | C11D—H11D | 0.9300 |
C15A—C16A | 1.390 (3) | C12D—C13D | 1.395 (3) |
C16A—C17A | 1.390 (3) | C12D—C17D | 1.403 (4) |
C16A—H16A | 0.9300 | C13D—C14D | 1.380 (4) |
C17A—H17A | 0.9300 | C13D—H13D | 0.9300 |
C19A—C20A | 1.508 (3) | C14D—C15D | 1.385 (4) |
C19A—H19A | 0.9700 | C14D—H14D | 0.9300 |
C19A—H19B | 0.9700 | C15D—C16D | 1.396 (4) |
C20A—C21A | 1.383 (4) | C16D—C17D | 1.378 (3) |
C20A—C25A | 1.391 (3) | C16D—H16D | 0.9300 |
C21A—C22A | 1.381 (4) | C17D—H17D | 0.9300 |
C21A—H21A | 0.9300 | C18D—S1D | 1.709 (4) |
C22A—C23A | 1.378 (4) | C18D—S1Y | 2.032 (11) |
C22A—H22A | 0.9300 | C26D—H26J | 0.9600 |
C23A—C24A | 1.372 (4) | C26D—H26K | 0.9600 |
C23A—H23A | 0.9300 | C26D—H26L | 0.9600 |
C24A—C25A | 1.389 (3) | C27D—H27J | 0.9600 |
C24A—H24A | 0.9300 | C27D—H27K | 0.9600 |
C25A—H25A | 0.9300 | C27D—H27L | 0.9600 |
C26A—H26A | 0.9600 | C1B—C2B | 1.382 (9) |
C26A—H26B | 0.9600 | C1B—C6B | 1.396 (7) |
C26A—H26C | 0.9600 | C1B—H1BA | 0.9300 |
C27A—H27A | 0.9600 | C2B—C3B | 1.384 (8) |
C27A—H27B | 0.9600 | C2B—H2BA | 0.9300 |
C27A—H27C | 0.9600 | C3B—C4B | 1.397 (8) |
S1B—C18B | 1.755 (2) | C4B—C5B | 1.381 (7) |
S1B—C19B | 1.804 (3) | C4B—H4BA | 0.9300 |
S2B—C18B | 1.657 (2) | C5B—C6B | 1.396 (7) |
N2B—C18B | 1.348 (3) | C5B—H5BA | 0.9300 |
N2B—N1X | 1.393 (9) | C6B—C7B | 1.454 (7) |
N2B—N1B | 1.402 (5) | C7B—C8B | 1.342 (7) |
N2B—H2N2 | 0.82 (3) | C7B—H7BA | 0.9300 |
O1B—C3B | 1.248 (9) | C8B—C9B | 1.466 (6) |
O1B—C26B | 1.423 (3) | C8B—H8BA | 0.9300 |
O1B—C3X | 1.613 (16) | N1B—C9B | 1.292 (6) |
O2B—C15X | 1.309 (19) | C9B—C10B | 1.473 (5) |
O2B—C15B | 1.406 (9) | C10B—C11B | 1.325 (6) |
O2B—C27B | 1.426 (3) | C10B—H10B | 0.9300 |
C19B—C20B | 1.509 (3) | C11B—C12B | 1.468 (6) |
C19B—H19C | 0.9700 | C11B—H11B | 0.9300 |
C19B—H19D | 0.9700 | C12B—C13B | 1.394 (7) |
C20B—C21B | 1.375 (4) | C12B—C17B | 1.396 (6) |
C20B—C25B | 1.384 (3) | C13B—C14B | 1.390 (7) |
C21B—C22B | 1.381 (4) | C13B—H13B | 0.9300 |
C21B—H21B | 0.9300 | C14B—C15B | 1.395 (9) |
C22B—C23B | 1.369 (5) | C14B—H14B | 0.9300 |
C22B—H22B | 0.9300 | C15B—C16B | 1.384 (8) |
C23B—C24B | 1.372 (4) | C16B—C17B | 1.389 (7) |
C23B—H23B | 0.9300 | C16B—H16B | 0.9300 |
C24B—C25B | 1.388 (4) | C17B—H17B | 0.9300 |
C24B—H24B | 0.9300 | C1X—C2X | 1.390 (14) |
C25B—H25B | 0.9300 | C1X—C6X | 1.400 (13) |
C26B—H26D | 0.9600 | C1X—H1XB | 0.9300 |
C26B—H26E | 0.9600 | C2X—C3X | 1.385 (14) |
C26B—H26F | 0.9600 | C2X—H2XB | 0.9300 |
C27B—H27D | 0.9600 | C3X—C4X | 1.403 (14) |
C27B—H27E | 0.9600 | C4X—C5X | 1.377 (12) |
C27B—H27F | 0.9600 | C4X—H4XB | 0.9300 |
S1C—C18C | 1.763 (2) | C5X—C6X | 1.412 (12) |
S1C—C19C | 1.825 (2) | C5X—H5XB | 0.9300 |
S2C—C18C | 1.648 (3) | C6X—C7X | 1.456 (12) |
N1C—C9C | 1.314 (3) | C7X—C8X | 1.336 (12) |
N1C—N2C | 1.362 (3) | C7X—H7XB | 0.9300 |
N2C—C18C | 1.352 (3) | C8X—C9X | 1.463 (11) |
N2C—H3N2 | 0.91 (3) | C8X—H8XB | 0.9300 |
O1C—C3C | 1.370 (3) | N1X—C9X | 1.284 (11) |
O1C—C26C | 1.427 (3) | C9X—C10X | 1.482 (11) |
O2C—C15C | 1.366 (3) | C10X—C11X | 1.321 (10) |
O2C—C27C | 1.436 (4) | C10X—H10E | 0.9300 |
C1C—C2C | 1.380 (3) | C11X—C12X | 1.486 (9) |
C1C—C6C | 1.389 (3) | C11X—H11E | 0.9300 |
C1C—H1CA | 0.9300 | C12X—C17X | 1.379 (11) |
C2C—C3C | 1.382 (3) | C12X—C13X | 1.387 (12) |
C2C—H2CA | 0.9300 | C13X—C14X | 1.390 (13) |
C3C—C4C | 1.386 (3) | C13X—H13E | 0.9300 |
C4C—C5C | 1.375 (3) | C14X—C15X | 1.387 (15) |
C4C—H4CA | 0.9300 | C14X—H14E | 0.9300 |
C5C—C6C | 1.400 (3) | C15X—C16X | 1.378 (14) |
C5C—H5CA | 0.9300 | C16X—C17X | 1.388 (13) |
C6C—C7C | 1.466 (3) | C16X—H16E | 0.9300 |
C7C—C8C | 1.331 (3) | C17X—H17E | 0.9300 |
C7C—H7CA | 0.9300 | S1D—C19D | 1.841 (6) |
C8C—C9C | 1.460 (3) | C19D—C20D | 1.520 (8) |
C8C—H8CA | 0.9300 | C19D—H19I | 0.9700 |
C9C—C10C | 1.476 (3) | C19D—H19J | 0.9700 |
C10C—C11C | 1.324 (3) | C20D—C25D | 1.375 (10) |
C10C—H10C | 0.9300 | C20D—C21D | 1.388 (8) |
C11C—C12C | 1.471 (3) | C21D—C22D | 1.358 (9) |
C11C—H11C | 0.9300 | C21D—H21E | 0.9300 |
C12C—C13C | 1.392 (3) | C22D—C23D | 1.359 (11) |
C12C—C17C | 1.398 (3) | C22D—H22E | 0.9300 |
C13C—C14C | 1.393 (4) | C23D—C24D | 1.342 (13) |
C13C—H13C | 0.9300 | C23D—H23E | 0.9300 |
C14C—C15C | 1.373 (4) | C24D—C25D | 1.390 (11) |
C14C—H14C | 0.9300 | C24D—H24E | 0.9300 |
C15C—C16C | 1.394 (4) | C25D—H25E | 0.9300 |
C16C—C17C | 1.376 (3) | S1Y—C19Y | 1.785 (12) |
C16C—H16C | 0.9300 | C19Y—C20Y | 1.508 (13) |
C17C—H17C | 0.9300 | C19Y—H19G | 0.9700 |
C19C—C20C | 1.506 (3) | C19Y—H19H | 0.9700 |
C19C—H19E | 0.9700 | C20Y—C25Y | 1.373 (14) |
C19C—H19F | 0.9700 | C20Y—C21Y | 1.378 (13) |
C20C—C25C | 1.390 (3) | C21Y—C22Y | 1.362 (13) |
C20C—C21C | 1.391 (3) | C21Y—H21D | 0.9300 |
C21C—C22C | 1.384 (4) | C22Y—C23Y | 1.367 (16) |
C21C—H21C | 0.9300 | C22Y—H22D | 0.9300 |
C22C—C23C | 1.375 (4) | C23Y—C24Y | 1.341 (18) |
C22C—H22C | 0.9300 | C23Y—H23D | 0.9300 |
C23C—C24C | 1.369 (4) | C24Y—C25Y | 1.389 (15) |
C23C—H23C | 0.9300 | C24Y—H24D | 0.9300 |
C24C—C25C | 1.385 (3) | C25Y—H25D | 0.9300 |
C18A—S1A—C19A | 101.27 (10) | H26H—C26C—H26I | 109.5 |
C9A—N1A—N2A | 120.07 (17) | O2C—C27C—H27G | 109.5 |
C18A—N2A—N1A | 118.15 (17) | O2C—C27C—H27H | 109.5 |
C18A—N2A—H1N2 | 115.8 (19) | H27G—C27C—H27H | 109.5 |
N1A—N2A—H1N2 | 126.1 (19) | O2C—C27C—H27I | 109.5 |
C3A—O1A—C26A | 118.0 (2) | H27G—C27C—H27I | 109.5 |
C15A—O2A—C27A | 117.6 (2) | H27H—C27C—H27I | 109.5 |
C6A—C1A—C2A | 122.6 (2) | C9D—N1D—N2D | 117.5 (2) |
C6A—C1A—H1AA | 118.7 | N1D—N2D—C18D | 119.7 (2) |
C2A—C1A—H1AA | 118.7 | N1D—N2D—H4N2 | 125 (2) |
C3A—C2A—C1A | 118.7 (2) | C18D—N2D—H4N2 | 115 (2) |
C3A—C2A—H2AA | 120.6 | C3D—O1D—C26D | 117.54 (19) |
C1A—C2A—H2AA | 120.6 | C15D—O2D—C27D | 117.7 (2) |
O1A—C3A—C2A | 125.1 (2) | C2D—C1D—C6D | 122.9 (2) |
O1A—C3A—C4A | 115.0 (2) | C2D—C1D—H1DA | 118.5 |
C2A—C3A—C4A | 119.8 (2) | C6D—C1D—H1DA | 118.5 |
C5A—C4A—C3A | 120.7 (2) | C1D—C2D—C3D | 118.7 (2) |
C5A—C4A—H4AA | 119.7 | C1D—C2D—H2DA | 120.7 |
C3A—C4A—H4AA | 119.7 | C3D—C2D—H2DA | 120.7 |
C4A—C5A—C6A | 120.8 (2) | O1D—C3D—C4D | 116.1 (2) |
C4A—C5A—H5AA | 119.6 | O1D—C3D—C2D | 124.2 (2) |
C6A—C5A—H5AA | 119.6 | C4D—C3D—C2D | 119.7 (2) |
C1A—C6A—C5A | 117.3 (2) | C5D—C4D—C3D | 120.6 (2) |
C1A—C6A—C7A | 119.8 (2) | C5D—C4D—H4DA | 119.7 |
C5A—C6A—C7A | 122.84 (19) | C3D—C4D—H4DA | 119.7 |
C8A—C7A—C6A | 127.2 (2) | C4D—C5D—C6D | 121.2 (2) |
C8A—C7A—H7AA | 116.4 | C4D—C5D—H5DA | 119.4 |
C6A—C7A—H7AA | 116.4 | C6D—C5D—H5DA | 119.4 |
C7A—C8A—C9A | 125.1 (2) | C1D—C6D—C5D | 116.8 (2) |
C7A—C8A—H8AA | 117.5 | C1D—C6D—C7D | 119.51 (19) |
C9A—C8A—H8AA | 117.5 | C5D—C6D—C7D | 123.6 (2) |
N1A—C9A—C8A | 125.80 (19) | C8D—C7D—C6D | 128.0 (2) |
N1A—C9A—C10A | 114.22 (18) | C8D—C7D—H7DA | 116.0 |
C8A—C9A—C10A | 119.91 (19) | C6D—C7D—H7DA | 116.0 |
C11A—C10A—C9A | 122.3 (2) | C7D—C8D—C9D | 123.8 (2) |
C11A—C10A—H10A | 118.9 | C7D—C8D—H8DA | 118.1 |
C9A—C10A—H10A | 118.9 | C9D—C8D—H8DA | 118.1 |
C10A—C11A—C12A | 126.6 (2) | N1D—C9D—C8D | 126.3 (2) |
C10A—C11A—H11A | 116.7 | N1D—C9D—C10D | 114.7 (2) |
C12A—C11A—H11A | 116.7 | C8D—C9D—C10D | 118.9 (2) |
C17A—C12A—C13A | 117.3 (2) | C11D—C10D—C9D | 125.1 (2) |
C17A—C12A—C11A | 123.2 (2) | C11D—C10D—H10D | 117.5 |
C13A—C12A—C11A | 119.5 (2) | C9D—C10D—H10D | 117.5 |
C14A—C13A—C12A | 121.7 (2) | C10D—C11D—C12D | 125.8 (2) |
C14A—C13A—H13A | 119.2 | C10D—C11D—H11D | 117.1 |
C12A—C13A—H13A | 119.2 | C12D—C11D—H11D | 117.1 |
C13A—C14A—C15A | 119.9 (2) | C13D—C12D—C17D | 116.7 (2) |
C13A—C14A—H14A | 120.0 | C13D—C12D—C11D | 120.4 (2) |
C15A—C14A—H14A | 120.0 | C17D—C12D—C11D | 122.9 (2) |
O2A—C15A—C16A | 124.4 (2) | C14D—C13D—C12D | 122.4 (3) |
O2A—C15A—C14A | 115.8 (2) | C14D—C13D—H13D | 118.8 |
C16A—C15A—C14A | 119.8 (2) | C12D—C13D—H13D | 118.8 |
C17A—C16A—C15A | 119.5 (2) | C13D—C14D—C15D | 119.8 (2) |
C17A—C16A—H16A | 120.3 | C13D—C14D—H14D | 120.1 |
C15A—C16A—H16A | 120.3 | C15D—C14D—H14D | 120.1 |
C16A—C17A—C12A | 121.8 (2) | O2D—C15D—C14D | 125.0 (2) |
C16A—C17A—H17A | 119.1 | O2D—C15D—C16D | 115.7 (2) |
C12A—C17A—H17A | 119.1 | C14D—C15D—C16D | 119.3 (2) |
N2A—C18A—S2A | 121.55 (15) | C17D—C16D—C15D | 120.1 (2) |
N2A—C18A—S1A | 112.85 (15) | C17D—C16D—H16D | 120.0 |
S2A—C18A—S1A | 125.60 (13) | C15D—C16D—H16D | 120.0 |
C20A—C19A—S1A | 109.27 (15) | C16D—C17D—C12D | 121.7 (2) |
C20A—C19A—H19A | 109.8 | C16D—C17D—H17D | 119.1 |
S1A—C19A—H19A | 109.8 | C12D—C17D—H17D | 119.1 |
C20A—C19A—H19B | 109.8 | N2D—C18D—S2D | 122.8 (2) |
S1A—C19A—H19B | 109.8 | N2D—C18D—S1D | 112.9 (2) |
H19A—C19A—H19B | 108.3 | S2D—C18D—S1D | 124.23 (17) |
C21A—C20A—C25A | 118.5 (2) | N2D—C18D—S1Y | 109.0 (3) |
C21A—C20A—C19A | 119.8 (2) | S2D—C18D—S1Y | 128.0 (2) |
C25A—C20A—C19A | 121.7 (2) | O1D—C26D—H26J | 109.5 |
C22A—C21A—C20A | 121.2 (2) | O1D—C26D—H26K | 109.5 |
C22A—C21A—H21A | 119.4 | H26J—C26D—H26K | 109.5 |
C20A—C21A—H21A | 119.4 | O1D—C26D—H26L | 109.5 |
C23A—C22A—C21A | 119.9 (2) | H26J—C26D—H26L | 109.5 |
C23A—C22A—H22A | 120.1 | H26K—C26D—H26L | 109.5 |
C21A—C22A—H22A | 120.1 | O2D—C27D—H27J | 109.5 |
C24A—C23A—C22A | 119.8 (2) | O2D—C27D—H27K | 109.5 |
C24A—C23A—H23A | 120.1 | H27J—C27D—H27K | 109.5 |
C22A—C23A—H23A | 120.1 | O2D—C27D—H27L | 109.5 |
C23A—C24A—C25A | 120.6 (2) | H27J—C27D—H27L | 109.5 |
C23A—C24A—H24A | 119.7 | H27K—C27D—H27L | 109.5 |
C25A—C24A—H24A | 119.7 | C2B—C1B—C6B | 123.5 (7) |
C24A—C25A—C20A | 120.0 (2) | C2B—C1B—H1BA | 118.2 |
C24A—C25A—H25A | 120.0 | C6B—C1B—H1BA | 118.2 |
C20A—C25A—H25A | 120.0 | C1B—C2B—C3B | 118.2 (7) |
O1A—C26A—H26A | 109.5 | C1B—C2B—H2BA | 120.9 |
O1A—C26A—H26B | 109.5 | C3B—C2B—H2BA | 120.9 |
H26A—C26A—H26B | 109.5 | O1B—C3B—C2B | 125.1 (7) |
O1A—C26A—H26C | 109.5 | O1B—C3B—C4B | 114.9 (7) |
H26A—C26A—H26C | 109.5 | C2B—C3B—C4B | 119.8 (7) |
H26B—C26A—H26C | 109.5 | C5B—C4B—C3B | 120.8 (7) |
O2A—C27A—H27A | 109.5 | C5B—C4B—H4BA | 119.6 |
O2A—C27A—H27B | 109.5 | C3B—C4B—H4BA | 119.6 |
H27A—C27A—H27B | 109.5 | C4B—C5B—C6B | 120.7 (7) |
O2A—C27A—H27C | 109.5 | C4B—C5B—H5BA | 119.6 |
H27A—C27A—H27C | 109.5 | C6B—C5B—H5BA | 119.6 |
H27B—C27A—H27C | 109.5 | C5B—C6B—C1B | 116.8 (7) |
C18B—S1B—C19B | 101.73 (11) | C5B—C6B—C7B | 125.0 (6) |
C18B—N2B—N1X | 107.4 (4) | C1B—C6B—C7B | 118.1 (7) |
C18B—N2B—N1B | 122.2 (3) | C8B—C7B—C6B | 124.7 (6) |
C18B—N2B—H2N2 | 115.3 (19) | C8B—C7B—H7BA | 117.7 |
N1X—N2B—H2N2 | 133 (2) | C6B—C7B—H7BA | 117.7 |
N1B—N2B—H2N2 | 122.3 (19) | C7B—C8B—C9B | 120.4 (5) |
C3B—O1B—C26B | 117.6 (4) | C7B—C8B—H8BA | 119.8 |
C26B—O1B—C3X | 116.9 (7) | C9B—C8B—H8BA | 119.8 |
C15X—O2B—C27B | 108.6 (9) | C9B—N1B—N2B | 121.8 (4) |
C15B—O2B—C27B | 121.0 (4) | N1B—C9B—C8B | 125.4 (4) |
N2B—C18B—S2B | 122.09 (17) | N1B—C9B—C10B | 116.2 (4) |
N2B—C18B—S1B | 112.17 (16) | C8B—C9B—C10B | 118.4 (4) |
S2B—C18B—S1B | 125.72 (14) | C11B—C10B—C9B | 124.1 (4) |
C20B—C19B—S1B | 107.82 (16) | C11B—C10B—H10B | 117.9 |
C20B—C19B—H19C | 110.1 | C9B—C10B—H10B | 117.9 |
S1B—C19B—H19C | 110.1 | C10B—C11B—C12B | 126.4 (4) |
C20B—C19B—H19D | 110.1 | C10B—C11B—H11B | 116.8 |
S1B—C19B—H19D | 110.1 | C12B—C11B—H11B | 116.8 |
H19C—C19B—H19D | 108.5 | C13B—C12B—C17B | 117.4 (4) |
C21B—C20B—C25B | 118.5 (2) | C13B—C12B—C11B | 119.9 (4) |
C21B—C20B—C19B | 120.1 (2) | C17B—C12B—C11B | 122.7 (4) |
C25B—C20B—C19B | 121.4 (2) | C14B—C13B—C12B | 122.1 (5) |
C20B—C21B—C22B | 121.0 (3) | C14B—C13B—H13B | 118.9 |
C20B—C21B—H21B | 119.5 | C12B—C13B—H13B | 118.9 |
C22B—C21B—H21B | 119.5 | C13B—C14B—C15B | 119.0 (7) |
C23B—C22B—C21B | 120.4 (3) | C13B—C14B—H14B | 120.5 |
C23B—C22B—H22B | 119.8 | C15B—C14B—H14B | 120.5 |
C21B—C22B—H22B | 119.8 | C16B—C15B—C14B | 120.0 (7) |
C22B—C23B—C24B | 119.2 (3) | C16B—C15B—O2B | 123.7 (8) |
C22B—C23B—H23B | 120.4 | C14B—C15B—O2B | 116.1 (6) |
C24B—C23B—H23B | 120.4 | C15B—C16B—C17B | 120.1 (6) |
C23B—C24B—C25B | 120.6 (3) | C15B—C16B—H16B | 120.0 |
C23B—C24B—H24B | 119.7 | C17B—C16B—H16B | 120.0 |
C25B—C24B—H24B | 119.7 | C16B—C17B—C12B | 121.3 (4) |
C20B—C25B—C24B | 120.2 (3) | C16B—C17B—H17B | 119.3 |
C20B—C25B—H25B | 119.9 | C12B—C17B—H17B | 119.3 |
C24B—C25B—H25B | 119.9 | C2X—C1X—C6X | 120.2 (13) |
O1B—C26B—H26D | 109.5 | C2X—C1X—H1XB | 119.9 |
O1B—C26B—H26E | 109.5 | C6X—C1X—H1XB | 119.9 |
H26D—C26B—H26E | 109.5 | C3X—C2X—C1X | 122.4 (15) |
O1B—C26B—H26F | 109.5 | C3X—C2X—H2XB | 118.8 |
H26D—C26B—H26F | 109.5 | C1X—C2X—H2XB | 118.8 |
H26E—C26B—H26F | 109.5 | C2X—C3X—C4X | 118.0 (14) |
O2B—C27B—H27D | 109.5 | C2X—C3X—O1B | 123.5 (13) |
O2B—C27B—H27E | 109.5 | C4X—C3X—O1B | 117.8 (13) |
H27D—C27B—H27E | 109.5 | C5X—C4X—C3X | 119.9 (13) |
O2B—C27B—H27F | 109.5 | C5X—C4X—H4XB | 120.1 |
H27D—C27B—H27F | 109.5 | C3X—C4X—H4XB | 120.1 |
H27E—C27B—H27F | 109.5 | C4X—C5X—C6X | 122.6 (14) |
C18C—S1C—C19C | 100.52 (11) | C4X—C5X—H5XB | 118.7 |
C9C—N1C—N2C | 119.70 (18) | C6X—C5X—H5XB | 118.7 |
C18C—N2C—N1C | 118.99 (19) | C1X—C6X—C5X | 116.9 (12) |
C18C—N2C—H3N2 | 110 (2) | C1X—C6X—C7X | 121.1 (13) |
N1C—N2C—H3N2 | 131 (2) | C5X—C6X—C7X | 121.9 (13) |
C3C—O1C—C26C | 117.62 (18) | C8X—C7X—C6X | 129.0 (13) |
C15C—O2C—C27C | 116.8 (3) | C8X—C7X—H7XB | 115.5 |
C2C—C1C—C6C | 122.4 (2) | C6X—C7X—H7XB | 115.5 |
C2C—C1C—H1CA | 118.8 | C7X—C8X—C9X | 123.2 (10) |
C6C—C1C—H1CA | 118.8 | C7X—C8X—H8XB | 118.4 |
C1C—C2C—C3C | 119.4 (2) | C9X—C8X—H8XB | 118.4 |
C1C—C2C—H2CA | 120.3 | C9X—N1X—N2B | 111.3 (7) |
C3C—C2C—H2CA | 120.3 | N1X—C9X—C8X | 125.6 (8) |
O1C—C3C—C2C | 124.0 (2) | N1X—C9X—C10X | 112.0 (8) |
O1C—C3C—C4C | 116.7 (2) | C8X—C9X—C10X | 122.3 (8) |
C2C—C3C—C4C | 119.2 (2) | C11X—C10X—C9X | 124.8 (8) |
C5C—C4C—C3C | 121.0 (2) | C11X—C10X—H10E | 117.6 |
C5C—C4C—H4CA | 119.5 | C9X—C10X—H10E | 117.6 |
C3C—C4C—H4CA | 119.5 | C10X—C11X—C12X | 124.1 (8) |
C4C—C5C—C6C | 120.7 (2) | C10X—C11X—H11E | 118.0 |
C4C—C5C—H5CA | 119.7 | C12X—C11X—H11E | 118.0 |
C6C—C5C—H5CA | 119.7 | C17X—C12X—C13X | 119.0 (7) |
C1C—C6C—C5C | 117.2 (2) | C17X—C12X—C11X | 118.6 (8) |
C1C—C6C—C7C | 118.6 (2) | C13X—C12X—C11X | 122.5 (9) |
C5C—C6C—C7C | 124.2 (2) | C12X—C13X—C14X | 118.4 (10) |
C8C—C7C—C6C | 127.7 (2) | C12X—C13X—H13E | 120.8 |
C8C—C7C—H7CA | 116.2 | C14X—C13X—H13E | 120.8 |
C6C—C7C—H7CA | 116.2 | C15X—C14X—C13X | 122.7 (13) |
C7C—C8C—C9C | 124.3 (2) | C15X—C14X—H14E | 118.6 |
C7C—C8C—H8CA | 117.8 | C13X—C14X—H14E | 118.6 |
C9C—C8C—H8CA | 117.8 | O2B—C15X—C16X | 130.1 (16) |
N1C—C9C—C8C | 126.8 (2) | O2B—C15X—C14X | 111.3 (13) |
N1C—C9C—C10C | 114.27 (19) | C16X—C15X—C14X | 118.2 (15) |
C8C—C9C—C10C | 118.89 (19) | C15X—C16X—C17X | 119.3 (12) |
C11C—C10C—C9C | 124.9 (2) | C15X—C16X—H16E | 120.3 |
C11C—C10C—H10C | 117.5 | C17X—C16X—H16E | 120.3 |
C9C—C10C—H10C | 117.5 | C12X—C17X—C16X | 122.2 (9) |
C10C—C11C—C12C | 125.9 (2) | C12X—C17X—H17E | 118.9 |
C10C—C11C—H11C | 117.1 | C16X—C17X—H17E | 118.9 |
C12C—C11C—H11C | 117.1 | C18D—S1D—C19D | 101.7 (3) |
C13C—C12C—C17C | 117.3 (2) | C20D—C19D—S1D | 110.8 (6) |
C13C—C12C—C11C | 119.6 (2) | C20D—C19D—H19I | 109.5 |
C17C—C12C—C11C | 123.0 (2) | S1D—C19D—H19I | 109.5 |
C12C—C13C—C14C | 121.8 (2) | C20D—C19D—H19J | 109.5 |
C12C—C13C—H13C | 119.1 | S1D—C19D—H19J | 109.5 |
C14C—C13C—H13C | 119.1 | H19I—C19D—H19J | 108.1 |
C15C—C14C—C13C | 119.6 (2) | C25D—C20D—C21D | 116.9 (7) |
C15C—C14C—H14C | 120.2 | C25D—C20D—C19D | 121.2 (7) |
C13C—C14C—H14C | 120.2 | C21D—C20D—C19D | 121.9 (8) |
O2C—C15C—C14C | 125.2 (2) | C22D—C21D—C20D | 121.4 (9) |
O2C—C15C—C16C | 115.1 (2) | C22D—C21D—H21E | 119.3 |
C14C—C15C—C16C | 119.7 (2) | C20D—C21D—H21E | 119.3 |
C17C—C16C—C15C | 120.3 (2) | C21D—C22D—C23D | 119.7 (8) |
C17C—C16C—H16C | 119.8 | C21D—C22D—H22E | 120.2 |
C15C—C16C—H16C | 119.8 | C23D—C22D—H22E | 120.2 |
C16C—C17C—C12C | 121.2 (2) | C24D—C23D—C22D | 121.6 (7) |
C16C—C17C—H17C | 119.4 | C24D—C23D—H23E | 119.2 |
C12C—C17C—H17C | 119.4 | C22D—C23D—H23E | 119.2 |
N2C—C18C—S2C | 122.25 (18) | C23D—C24D—C25D | 118.6 (8) |
N2C—C18C—S1C | 113.37 (18) | C23D—C24D—H24E | 120.7 |
S2C—C18C—S1C | 124.37 (14) | C25D—C24D—H24E | 120.7 |
C20C—C19C—S1C | 108.63 (15) | C20D—C25D—C24D | 121.6 (8) |
C20C—C19C—H19E | 110.0 | C20D—C25D—H25E | 119.2 |
S1C—C19C—H19E | 110.0 | C24D—C25D—H25E | 119.2 |
C20C—C19C—H19F | 110.0 | C19Y—S1Y—C18D | 96.7 (5) |
S1C—C19C—H19F | 110.0 | C20Y—C19Y—S1Y | 109.0 (9) |
H19E—C19C—H19F | 108.3 | C20Y—C19Y—H19G | 109.9 |
C25C—C20C—C21C | 118.6 (2) | S1Y—C19Y—H19G | 109.9 |
C25C—C20C—C19C | 120.9 (2) | C20Y—C19Y—H19H | 109.9 |
C21C—C20C—C19C | 120.5 (2) | S1Y—C19Y—H19H | 109.9 |
C22C—C21C—C20C | 120.5 (2) | H19G—C19Y—H19H | 108.3 |
C22C—C21C—H21C | 119.8 | C25Y—C20Y—C21Y | 118.4 (14) |
C20C—C21C—H21C | 119.8 | C25Y—C20Y—C19Y | 123.5 (14) |
C23C—C22C—C21C | 120.3 (2) | C21Y—C20Y—C19Y | 117.3 (13) |
C23C—C22C—H22C | 119.9 | C22Y—C21Y—C20Y | 121.4 (13) |
C21C—C22C—H22C | 119.9 | C22Y—C21Y—H21D | 119.3 |
C24C—C23C—C22C | 119.8 (2) | C20Y—C21Y—H21D | 119.3 |
C24C—C23C—H23C | 120.1 | C21Y—C22Y—C23Y | 119.0 (14) |
C22C—C23C—H23C | 120.1 | C21Y—C22Y—H22D | 120.5 |
C23C—C24C—C25C | 120.6 (2) | C23Y—C22Y—H22D | 120.5 |
C23C—C24C—H24C | 119.7 | C24Y—C23Y—C22Y | 119.9 (13) |
C25C—C24C—H24C | 119.7 | C24Y—C23Y—H23D | 120.1 |
C24C—C25C—C20C | 120.2 (2) | C22Y—C23Y—H23D | 120.1 |
C24C—C25C—H25C | 119.9 | C23Y—C24Y—C25Y | 121.8 (15) |
C20C—C25C—H25C | 119.9 | C23Y—C24Y—H24D | 119.1 |
O1C—C26C—H26G | 109.5 | C25Y—C24Y—H24D | 119.1 |
O1C—C26C—H26H | 109.5 | C20Y—C25Y—C24Y | 118.0 (15) |
H26G—C26C—H26H | 109.5 | C20Y—C25Y—H25D | 121.0 |
O1C—C26C—H26I | 109.5 | C24Y—C25Y—H25D | 121.0 |
H26G—C26C—H26I | 109.5 | ||
C9A—N1A—N2A—C18A | −178.1 (2) | C2D—C1D—C6D—C5D | −0.4 (4) |
C6A—C1A—C2A—C3A | −0.1 (4) | C2D—C1D—C6D—C7D | 178.3 (2) |
C26A—O1A—C3A—C2A | 2.8 (4) | C4D—C5D—C6D—C1D | 1.3 (4) |
C26A—O1A—C3A—C4A | −178.7 (3) | C4D—C5D—C6D—C7D | −177.3 (2) |
C1A—C2A—C3A—O1A | 178.2 (2) | C1D—C6D—C7D—C8D | 172.1 (2) |
C1A—C2A—C3A—C4A | −0.3 (4) | C5D—C6D—C7D—C8D | −9.3 (4) |
O1A—C3A—C4A—C5A | −178.0 (2) | C6D—C7D—C8D—C9D | 176.0 (2) |
C2A—C3A—C4A—C5A | 0.6 (4) | N2D—N1D—C9D—C8D | −7.2 (3) |
C3A—C4A—C5A—C6A | −0.5 (4) | N2D—N1D—C9D—C10D | 177.91 (19) |
C2A—C1A—C6A—C5A | 0.2 (3) | C7D—C8D—C9D—N1D | 156.8 (2) |
C2A—C1A—C6A—C7A | −178.5 (2) | C7D—C8D—C9D—C10D | −28.4 (3) |
C4A—C5A—C6A—C1A | 0.1 (3) | N1D—C9D—C10D—C11D | −15.4 (3) |
C4A—C5A—C6A—C7A | 178.8 (2) | C8D—C9D—C10D—C11D | 169.3 (2) |
C1A—C6A—C7A—C8A | −175.4 (2) | C9D—C10D—C11D—C12D | 172.4 (2) |
C5A—C6A—C7A—C8A | 5.9 (4) | C10D—C11D—C12D—C13D | 167.0 (3) |
C6A—C7A—C8A—C9A | −178.1 (2) | C10D—C11D—C12D—C17D | −15.9 (4) |
N2A—N1A—C9A—C8A | −1.5 (3) | C17D—C12D—C13D—C14D | 2.3 (4) |
N2A—N1A—C9A—C10A | 175.53 (19) | C11D—C12D—C13D—C14D | 179.6 (3) |
C7A—C8A—C9A—N1A | −175.0 (2) | C12D—C13D—C14D—C15D | −0.4 (5) |
C7A—C8A—C9A—C10A | 8.1 (3) | C27D—O2D—C15D—C14D | 0.7 (4) |
N1A—C9A—C10A—C11A | −37.5 (3) | C27D—O2D—C15D—C16D | −177.9 (2) |
C8A—C9A—C10A—C11A | 139.7 (2) | C13D—C14D—C15D—O2D | 179.4 (3) |
C9A—C10A—C11A—C12A | −176.9 (2) | C13D—C14D—C15D—C16D | −2.1 (4) |
C10A—C11A—C12A—C17A | −19.6 (4) | O2D—C15D—C16D—C17D | −178.8 (2) |
C10A—C11A—C12A—C13A | 158.7 (2) | C14D—C15D—C16D—C17D | 2.5 (4) |
C17A—C12A—C13A—C14A | 1.0 (4) | C15D—C16D—C17D—C12D | −0.5 (4) |
C11A—C12A—C13A—C14A | −177.3 (2) | C13D—C12D—C17D—C16D | −1.9 (4) |
C12A—C13A—C14A—C15A | −1.2 (4) | C11D—C12D—C17D—C16D | −179.1 (2) |
C27A—O2A—C15A—C16A | 0.9 (4) | N1D—N2D—C18D—S2D | 178.81 (18) |
C27A—O2A—C15A—C14A | −179.9 (3) | N1D—N2D—C18D—S1D | 2.6 (3) |
C13A—C14A—C15A—O2A | −178.6 (2) | N1D—N2D—C18D—S1Y | −6.9 (4) |
C13A—C14A—C15A—C16A | 0.7 (4) | C6B—C1B—C2B—C3B | 3 (2) |
O2A—C15A—C16A—C17A | 179.0 (2) | C26B—O1B—C3B—C2B | 7.3 (15) |
C14A—C15A—C16A—C17A | −0.2 (4) | C26B—O1B—C3B—C4B | −177.9 (7) |
C15A—C16A—C17A—C12A | 0.1 (4) | C1B—C2B—C3B—O1B | 173.4 (13) |
C13A—C12A—C17A—C16A | −0.5 (3) | C1B—C2B—C3B—C4B | −1 (2) |
C11A—C12A—C17A—C16A | 177.8 (2) | O1B—C3B—C4B—C5B | −175.3 (10) |
N1A—N2A—C18A—S2A | 175.75 (15) | C2B—C3B—C4B—C5B | −0.2 (18) |
N1A—N2A—C18A—S1A | −3.4 (3) | C3B—C4B—C5B—C6B | −0.1 (16) |
C19A—S1A—C18A—N2A | −179.45 (18) | C4B—C5B—C6B—C1B | 1.7 (15) |
C19A—S1A—C18A—S2A | 1.47 (19) | C4B—C5B—C6B—C7B | −176.6 (9) |
C18A—S1A—C19A—C20A | 160.53 (19) | C2B—C1B—C6B—C5B | −3 (2) |
S1A—C19A—C20A—C21A | −96.9 (2) | C2B—C1B—C6B—C7B | 175.2 (13) |
S1A—C19A—C20A—C25A | 85.0 (2) | C5B—C6B—C7B—C8B | 16.4 (14) |
C25A—C20A—C21A—C22A | 1.1 (4) | C1B—C6B—C7B—C8B | −162.0 (9) |
C19A—C20A—C21A—C22A | −177.1 (2) | C6B—C7B—C8B—C9B | 178.0 (7) |
C20A—C21A—C22A—C23A | −0.9 (4) | C18B—N2B—N1B—C9B | −175.6 (4) |
C21A—C22A—C23A—C24A | 0.1 (4) | N2B—N1B—C9B—C8B | 8.6 (7) |
C22A—C23A—C24A—C25A | 0.5 (4) | N2B—N1B—C9B—C10B | −170.3 (4) |
C23A—C24A—C25A—C20A | −0.3 (4) | C7B—C8B—C9B—N1B | −147.3 (6) |
C21A—C20A—C25A—C24A | −0.5 (3) | C7B—C8B—C9B—C10B | 31.5 (8) |
C19A—C20A—C25A—C24A | 177.6 (2) | N1B—C9B—C10B—C11B | 37.3 (6) |
N1X—N2B—C18B—S2B | −158.8 (4) | C8B—C9B—C10B—C11B | −141.6 (4) |
N1B—N2B—C18B—S2B | 178.0 (3) | C9B—C10B—C11B—C12B | −179.1 (4) |
N1X—N2B—C18B—S1B | 22.3 (5) | C10B—C11B—C12B—C13B | −162.8 (4) |
N1B—N2B—C18B—S1B | −0.9 (4) | C10B—C11B—C12B—C17B | 18.4 (6) |
C19B—S1B—C18B—N2B | 178.15 (18) | C17B—C12B—C13B—C14B | −1.1 (9) |
C19B—S1B—C18B—S2B | −0.70 (19) | C11B—C12B—C13B—C14B | −180.0 (7) |
C18B—S1B—C19B—C20B | −160.74 (18) | C12B—C13B—C14B—C15B | 1.1 (18) |
S1B—C19B—C20B—C21B | 93.7 (3) | C13B—C14B—C15B—C16B | 0 (3) |
S1B—C19B—C20B—C25B | −85.7 (3) | C13B—C14B—C15B—O2B | 175.8 (12) |
C25B—C20B—C21B—C22B | −2.6 (4) | C27B—O2B—C15B—C16B | −4 (3) |
C19B—C20B—C21B—C22B | 177.9 (2) | C27B—O2B—C15B—C14B | −179.1 (12) |
C20B—C21B—C22B—C23B | 0.6 (4) | C14B—C15B—C16B—C17B | −2 (3) |
C21B—C22B—C23B—C24B | 1.9 (4) | O2B—C15B—C16B—C17B | −176.8 (14) |
C22B—C23B—C24B—C25B | −2.3 (4) | C15B—C16B—C17B—C12B | 1.9 (15) |
C21B—C20B—C25B—C24B | 2.2 (4) | C13B—C12B—C17B—C16B | −0.4 (8) |
C19B—C20B—C25B—C24B | −178.4 (2) | C11B—C12B—C17B—C16B | 178.4 (6) |
C23B—C24B—C25B—C20B | 0.3 (4) | C6X—C1X—C2X—C3X | −1 (5) |
C9C—N1C—N2C—C18C | −179.3 (2) | C1X—C2X—C3X—C4X | 1 (5) |
C6C—C1C—C2C—C3C | 0.6 (4) | C1X—C2X—C3X—O1B | −169 (3) |
C26C—O1C—C3C—C2C | −20.9 (3) | C26B—O1B—C3X—C2X | −6 (3) |
C26C—O1C—C3C—C4C | 159.7 (2) | C26B—O1B—C3X—C4X | −176.5 (14) |
C1C—C2C—C3C—O1C | −178.0 (2) | C2X—C3X—C4X—C5X | 0 (4) |
C1C—C2C—C3C—C4C | 1.4 (4) | O1B—C3X—C4X—C5X | 170.9 (18) |
O1C—C3C—C4C—C5C | 177.7 (2) | C3X—C4X—C5X—C6X | −1 (3) |
C2C—C3C—C4C—C5C | −1.8 (4) | C2X—C1X—C6X—C5X | 0 (4) |
C3C—C4C—C5C—C6C | 0.1 (4) | C2X—C1X—C6X—C7X | 175 (3) |
C2C—C1C—C6C—C5C | −2.2 (4) | C4X—C5X—C6X—C1X | 1 (3) |
C2C—C1C—C6C—C7C | 175.4 (2) | C4X—C5X—C6X—C7X | −174.5 (18) |
C4C—C5C—C6C—C1C | 1.9 (4) | C1X—C6X—C7X—C8X | −163.8 (19) |
C4C—C5C—C6C—C7C | −175.6 (2) | C5X—C6X—C7X—C8X | 12 (3) |
C1C—C6C—C7C—C8C | −161.5 (3) | C6X—C7X—C8X—C9X | 174.1 (14) |
C5C—C6C—C7C—C8C | 16.0 (4) | C18B—N2B—N1X—C9X | −177.1 (6) |
C6C—C7C—C8C—C9C | 175.7 (2) | N2B—N1X—C9X—C8X | −2.0 (13) |
N2C—N1C—C9C—C8C | −0.1 (3) | N2B—N1X—C9X—C10X | 178.1 (7) |
N2C—N1C—C9C—C10C | −177.19 (19) | C7X—C8X—C9X—N1X | −147.7 (13) |
C7C—C8C—C9C—N1C | 175.7 (2) | C7X—C8X—C9X—C10X | 32.3 (16) |
C7C—C8C—C9C—C10C | −7.4 (3) | N1X—C9X—C10X—C11X | −148.7 (8) |
N1C—C9C—C10C—C11C | −26.9 (3) | C8X—C9X—C10X—C11X | 31.4 (13) |
C8C—C9C—C10C—C11C | 155.8 (2) | C9X—C10X—C11X—C12X | 173.8 (7) |
C9C—C10C—C11C—C12C | 177.1 (2) | C10X—C11X—C12X—C17X | −153.4 (8) |
C10C—C11C—C12C—C13C | 173.9 (2) | C10X—C11X—C12X—C13X | 26.5 (12) |
C10C—C11C—C12C—C17C | −7.4 (4) | C17X—C12X—C13X—C14X | 3.0 (18) |
C17C—C12C—C13C—C14C | 1.7 (4) | C11X—C12X—C13X—C14X | −176.9 (14) |
C11C—C12C—C13C—C14C | −179.6 (2) | C12X—C13X—C14X—C15X | 0 (4) |
C12C—C13C—C14C—C15C | −0.6 (4) | C27B—O2B—C15X—C16X | 3 (6) |
C27C—O2C—C15C—C14C | 2.1 (4) | C27B—O2B—C15X—C14X | 174 (3) |
C27C—O2C—C15C—C16C | −177.4 (3) | C13X—C14X—C15X—O2B | −177 (2) |
C13C—C14C—C15C—O2C | 179.5 (3) | C13X—C14X—C15X—C16X | −4 (6) |
C13C—C14C—C15C—C16C | −1.1 (4) | O2B—C15X—C16X—C17X | 176 (4) |
O2C—C15C—C16C—C17C | −178.8 (2) | C14X—C15X—C16X—C17X | 5 (6) |
C14C—C15C—C16C—C17C | 1.6 (4) | C13X—C12X—C17X—C16X | −2.1 (15) |
C15C—C16C—C17C—C12C | −0.5 (4) | C11X—C12X—C17X—C16X | 177.8 (11) |
C13C—C12C—C17C—C16C | −1.1 (3) | C15X—C16X—C17X—C12X | −2 (3) |
C11C—C12C—C17C—C16C | −179.8 (2) | N2D—C18D—S1D—C19D | 174.9 (3) |
N1C—N2C—C18C—S2C | −172.08 (16) | S2D—C18D—S1D—C19D | −1.3 (3) |
N1C—N2C—C18C—S1C | 7.0 (3) | C18D—S1D—C19D—C20D | −162.9 (6) |
C19C—S1C—C18C—N2C | 176.62 (17) | S1D—C19D—C20D—C25D | 70.4 (13) |
C19C—S1C—C18C—S2C | −4.35 (19) | S1D—C19D—C20D—C21D | −108.5 (13) |
C18C—S1C—C19C—C20C | −163.37 (17) | C25D—C20D—C21D—C22D | 5 (2) |
S1C—C19C—C20C—C25C | 67.0 (3) | C19D—C20D—C21D—C22D | −176.0 (12) |
S1C—C19C—C20C—C21C | −114.6 (2) | C20D—C21D—C22D—C23D | −3 (2) |
C25C—C20C—C21C—C22C | 0.0 (4) | C21D—C22D—C23D—C24D | 0.0 (17) |
C19C—C20C—C21C—C22C | −178.3 (2) | C22D—C23D—C24D—C25D | 0.5 (15) |
C20C—C21C—C22C—C23C | 0.2 (4) | C21D—C20D—C25D—C24D | −4 (2) |
C21C—C22C—C23C—C24C | −0.4 (4) | C19D—C20D—C25D—C24D | 176.6 (11) |
C22C—C23C—C24C—C25C | 0.3 (4) | C23D—C24D—C25D—C20D | 1.8 (19) |
C23C—C24C—C25C—C20C | −0.1 (4) | C18D—S1Y—C19Y—C20Y | −130.3 (13) |
C21C—C20C—C25C—C24C | −0.1 (4) | S1Y—C19Y—C20Y—C25Y | 56 (3) |
C19C—C20C—C25C—C24C | 178.2 (2) | S1Y—C19Y—C20Y—C21Y | −135 (2) |
C9D—N1D—N2D—C18D | 179.8 (2) | C25Y—C20Y—C21Y—C22Y | −13 (4) |
C6D—C1D—C2D—C3D | −1.0 (4) | C19Y—C20Y—C21Y—C22Y | 177 (2) |
C26D—O1D—C3D—C4D | 175.9 (3) | C20Y—C21Y—C22Y—C23Y | 7 (4) |
C26D—O1D—C3D—C2D | −5.0 (4) | C21Y—C22Y—C23Y—C24Y | −1 (3) |
C1D—C2D—C3D—O1D | −177.4 (2) | C22Y—C23Y—C24Y—C25Y | 2 (3) |
C1D—C2D—C3D—C4D | 1.6 (4) | C21Y—C20Y—C25Y—C24Y | 14 (4) |
O1D—C3D—C4D—C5D | 178.4 (2) | C19Y—C20Y—C25Y—C24Y | −177 (2) |
C2D—C3D—C4D—C5D | −0.8 (4) | C23Y—C24Y—C25Y—C20Y | −8 (4) |
C3D—C4D—C5D—C6D | −0.8 (4) |
Cg1, Cg2 and Cg3 are the centroids of the C12B–C17B, C12C–C17C and C1B–C6B rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C24A—H24A···O2B | 0.93 | 2.57 | 3.262 (3) | 131 |
C21A—H21A···O1C | 0.93 | 2.40 | 3.249 (3) | 152 |
C21B—H21B···O1Bi | 0.93 | 2.33 | 3.240 (4) | 167 |
N2C—H3N2···S2Cii | 0.91 (4) | 2.53 (4) | 3.435 (2) | 179 (3) |
C17C—H17C···O1Diii | 0.93 | 2.53 | 3.381 (3) | 152 |
N2A—H1N2···S2Aiv | 0.81 (3) | 2.69 (3) | 3.473 (2) | 161 (2) |
N2B—H2N2···S2Dv | 0.82 (3) | 2.65 (3) | 3.461 (2) | 171 (3) |
N2D—H4N2···S2Bv | 0.91 (4) | 2.61 (4) | 3.517 (2) | 174 (3) |
C14C—H14C···Cg1iv | 0.93 | 2.80 | 3.558 (5) | 139 |
C16A—H16A···Cg2ii | 0.93 | 2.80 | 3.680 (2) | 158 |
C2D—H2DA···Cg3 | 0.93 | 2.94 | 3.700 (5) | 140 |
Symmetry codes: (i) −x, −y+2, −z; (ii) −x+2, −y, −z+1; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y, −z+1; (v) −x+1, −y+2, −z. |
Torsion angles for the minor disorder component were omitted. |
Molecule | τ | A | B | C | D |
C2—C3—O1—C26 | τ1 | -2.8 (4) | -7.3 (15) | 20.9 (3) | 5.0 (4) |
C9—N1—N2—C18 | τ7 | -178.1 (2) | -175.6 (4) | -179.3 (2) | 179.7 (2) |
C5—C6—C7—C8 | τ2 | 5.9 (4) | 16.4 (13) | 15.9 (4) | -9.3 (4) |
N1—N2—C18—S1 | τ8 | 175.76 (16) | -0.9 (3) | 6.9 (3) | 2.6 (3) |
N1—C9—C8—C7 | τ3 | 175.0 (2) | 147.4 (6) | -175.7 (2) | -156.8 (2) |
N2—C18—S1—C19 | τ9 | 179.43 (17) | -178.15 (17) | -176.64 (17) | -174.9 (3) |
N1—C9—C10—C11 | τ4 | -37.5 (3) | -37.4 (7) | -26.9 (3) | -15.3 (3) |
S1—C19—C20—C21 | τ10 | 160.53 (17) | -160.75 (17) | -163.36 (16) | -162.9 (6) |
C17—C12—C11—C10 | τ5 | 19.6 (4) | -18.4 (7) | 7.5 (3) | 15.9 (3) |
S1—C19—C20—C21 | τ11 | -97.0 (2) | 93.7 (3) | -114.6 (2) | -108.6 (12) |
C16—C15—O2—C27 | τ6 | -0.9 (4) | 4.1 (16) | 177.5 (3) | 177.9 (2) |
Dihedral angle 1 is the dihedral angle between the mean planes of the 4-methoxyphenyl rings; dihedral angle 2 is the dihedral angle between the mean planes of the benzyl (C20–C25) and 4-methoxyphenyl (C1–C6) rings; dihedral angle 3 is the dihedral angle between the mean planes of the benzyl (C20–C25) and the 4-methoxyphenyl (C12–C17) rings. |
Molecule | Dihedral angle 1 | Dihedral angle 2 | Dihedral angle 3 |
A | 56.72 (11) | 85.02 (11) | 72.11 (2) |
B | 89.6 (5) | 31.6 (5) | 64.9 (3) |
C | 23.59 (12) | 84.46 (12) | 86.00 (13) |
D | 60.82 (12) | 36.6 (8) | 89.9 (8) |
Two sets of torsion angles are stated for compounds EXINAB, QORJAK, SIMMUX, VOJGUX and WUPGIX because there are two molecules in their asymmetric units. The molecule with disorder in the structure of compound ZENLIN was omitted from this table. |
Compound | R1 | τ7 | τ8 | τ9 | τ10 | τ11 |
ABOROA (Manan et al., 2011) | 5-fluoro-2-oxo-1,2-dihydro-3H-indol-3-ylidenyl | 175.1 | 5.0 | -176.8 | 168.2 | -98.3 |
ABORUG (Manan et al., 2011) | 5-bromo-2-oxo-1,2-dihydro-3H-indol-3-ylidenyl | -178.5 | -9.1 | 176.9 | -108.0 | -84.1 |
ABOSAN (Manan et al., 2011) | 5-chloro-2-oxo-1,2-dihydro-3H-indol-3-ylidenyl | -178.8 | -7.7 | 177.5 | -110.4 | -81.8 |
BAHWIT (Md Yusof et al., 2015) | 2-methoxybenzylidenyl | -179.1 | 2.6 | -178.0 | -177.7 | -85.7 |
BAHWOZ (Md Yusof et al., 2015) | 3-methoxybenzylidenyl | -178.0 | -1.2 | -178.1 | 173.8 | -80.1 |
CEFBIB (Islam et al., 2016a) | 2,4,5-trimethoxybenzylidenyl | 179.6 | -5.2 | -177.9 | 173.4 | -79.7 |
COBQUH (Mirza et al., 2014) | pyridin-2-ylmethylenyl | -177.2 | -5.3 | -177.2 | -176.0 | -68.7 |
DATFEK (Khoo et al., 2005) | furan-2-yl)ethylidenyl | 178.6 | 1.7 | 180.0 | 180.0 | -72.5 |
EDETUD (How et al., 2007) | 1-(3-pyridyl)ethylidenyl | -179.2 | 4.9 | -179.8 | -165.8 | -87.5 |
EHIXUQ (Yusof et al., 2016) | 2-hydroxy-3-methoxybenzylidenyl | 177.4 | 1.8 | 179.9 | -173.3 | -101.2 |
EMEBAA (Ravoof et al., 2011) | bis(pyridin-2-yl)methylenyl | -165.7 | 1.4 | 175.4 | 176.2 | -83.4 |
EPOFAR (Ali et al., 2011) | 2-oxo-1,2-dihydro-3H-indol-3-ylidenyl | 176.5 | -4.5 | -176.2 | 165.0 | -95.5 |
EVITUZ (Shan et al., 2011a) | 2-nitrobenzylidenyl | 170.6 | 3.6 | 179.4 | -80.1 | 132.1 |
EXINAB (Shan et al., 2011b) | 2-methylbenzylidenyl | -174.0, -176.9 | -2.7, -4.9 | -178.7, -177.4 | 174.2, 175.6 | -68.2, -68.7 |
GUMJUV (Break et al., 2013) | 4-chlorophenyl)ethylidenyl | -172.7 | -0.3 | -179.3 | 86.8 | 68.1 |
HELZIK (Omar et al., 2018) | 1-(6-methylpyridin-2-yl)ethylidenyl | -177.7 | -1.6 | -176.0 | 171.6 | -108.0 |
IFUTUZ (Khaledi et al., 2008a) | 1H-indol-3-ylmethylidenyl | -172.7 | 2.6 | 179.0 | 103.7 | -68.2 |
JAMMOA (Ali et al., 2004) | quinolinyl-2-methylenyl | 177.9 | 0.8 | 177.5 | -171.0 | 101.8 |
KAGZOK (Ravoof et al., 2015) | 1-(5-methylpyridin-2-yl)ethylidenyl | -176.9 | -5.6 | -173.2 | 164.7 | -77.8 |
KUCRAC (Hamid et al., 2009) | 1-(pyrazin-2-yl)ethylidenyl | 178.4 | 0.6 | 178.8 | 174.7 | -70.0 |
KUCZUD (Xu et al., 1991) | pyridine-N-oxide-2-yl)methylidenyl | -171.4 | -2.0 | 176.5 | -161.7 | -92.2 |
LOBSEB (Shan et al., 2008b) | furan-2-ylmethylenyl | 173.8 | -0.5 | 179.7 | 177.1 | -93.0 |
LOBVOO (Tarafder et al., 2008) | (E)-3-phenylallylidenyl | -177.4 | 3.0 | 177.6 | -175.3 | -102.7 |
LOJBUI (Khaledi et al., 2008b) | 1-methyl-1H-indol-2-ylmethylenyl | 179.1 | -2.3 | -179.1 | 172.9 | -78.9 |
LOJLIG (Khaledi et al., 2008b) | diphenylmethylenyl | 170.5 | -1.2 | -175.2 | 164.8 | -83.8 |
LUBNIH (Zangrando et al., 2015) | 1-(3-hydroxyphenyl)ethylidenyl | -177.5 | -0.8 | 173.7 | 180.0 | -71.1 |
NIZBUV (Omar et al., 2014) | 1-(4-methylpyridin-2-yl)ethylidenyl | -178.4 | 0.0 | -175.8 | -95.9 | -141.1 |
OQOWOH (Akbar Ali et al., 2011) | bis(pyridin-2-yl)methylenyl | 165.1 | 1.9 | -177.2 | -180.0 | -83.8 |
PEWLEL (Li et al., 2012) | phenyl(pyridin-2-yl)methylenyl | -177.0 | 4.6 | -173.1 | 87.6 | -119.2 |
QORJAK (Tan et al., 2015) | 3,4-dimethoxybenzylidenyl | 169.2, -170.4 | -3.1, 3.7 | -179.5, 175.1 | 169.5, -168.8 | -118.8, -105.7 |
QUCLIL (Biswal et al., 2015) | 1-(2-hydroxyphenyl)ethylidene2-hydroxyphenyl)ethylidenyl | 176.7 | 0.6 | -173.3 | 171.2 | -115.5 |
RIYZOP (Shan et al., 2008a) | benzylidenyl | 177.1 | 0.1 | 178.5 | 171.8 | -80.0 |
RUGLAH (Li et al., 2009) | 3-nitrobenzylidenyl | 178.3 | -2.9 | -177.5 | 173.1 | -85.5 |
SALSEE (Zhang et al., 2004) | 4-((2-hydroxyethyl)methylamino)benzylidenyl | -166.4 | 0.9 | -176.8 | 170.4 | -88.4 |
SIMMUX (Qiu & Luo, 2007) | 2-bromobenzylidenyl | 175.6, -173.9 | 2.6, -5.6 | 178.8, -176.3 | -170.6, 173.6 | -115.6, 75.2 |
TADVEC (Islam et al., 2016b) | 3,4,5-trimethoxybenzylidenyl | -179.4 | -5.1 | -177.1 | 174.9 | -73.3 |
TIFSEH (Roy et al., 2007) | 2-methylthio-6-methyl-4-pyrimidyl)methylenyl | -177.8 | 0.6 | -178.4 | 164.9 | -76.6 |
UWATOD (Flörke & Boshaala, 2016) | 1-phenylethylidenyl | 172.4 | -4.0 | -173.3 | 159.5 | -102.0 |
VOJCUT (Khaledi et al., 2008c) | 1-methyl-1H-indol-3-ylmethylidenyl | -177.2 | -1.7 | -176.0 | -101.3 | -129.4 |
VOJGUX (Shi et al., 2008) | 2-chlorobenzylidenyl | -174.7, 178.3 | -2.0, 0.3 | -179.3, 176.9 | -174.0, -174.1 | -80.3, -110.1 |
WADGAK (Chan et al., 2003) | 1-(thiophen-2-yl)ethylidenyl | 174.8 | -5.8 | 177.8 | 77.6 | 17.1 |
WUPGIX (Tarafder et al., 2002) | 5-methylfuran-2-yl)methylenyl | -169.2, 179.8 | -0.2, 1.5 | 179.7, -176.3 | -173.6, -171.7 | -100.8, -77.9 |
YAHDAO (Fan et al., 2011a) | 4-methoxybenzylidenyl | -175.8 | 1.4 | -179.5 | -178.9 | -87.9 |
YAHDUI (Fan et al., 2011b) | 2-bromo-5-methoxybenzylidenyl | 177.8 | -3.6 | -176.0 | 174.9 | 119.2 |
ZENLIN (Fun et al., 1995) | 4-(dimethylamino)benzylidenyl | -180.0 | 1.3 | 179.9 | -178.0 | -97.1 |
Funding information
We thank the Universiti Putra Malaysia for the use of their facilities and the University of Anbar, Ministry of Higher Education, in Iraq for a scholarship (NAT). This research was funded by the UPM under the Research University Grant Scheme (RUGS No. 05–01-11–1234RU).
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