organic compounds
Z)-2-{(5Z)-5-[3-fluoro-2-(4-phenylpiperidin-1-yl)benzylidene]-4-oxo-3-(p-tolyl)-1,3-thiazolidin-2-ylidene}-N-(p-tolyl)ethanethioamide dimethyl sulfoxide monosolvate
of (2aUral Federal University, 19 Mira Str., Ekaterinburg 620002, Russian Federation, and bI. Ya. Postovsky Institute of Organic Synthesis, 22 S. Kovalevskoy Str., Ekaterinburg 620990, Russian Federation
*Correspondence e-mail: lili.khamidullina@gmail.com
The title compound, C37H34FN3OS2·C2H6OS, was obtained by the Knoevenagel condensation. The thiazolidine ring is essentially planar (r.m.s. deviation = 0.025 Å) and forms dihedral angles of 4.2 (3), 68.60 (14) and 39.57 (15)° with the attached thioamide group, p-tolyl group benzene ring and fluoro-substituted benzene ring, respectively. The exocyclic double bonds are in a Z configuration. In the crystal, the dimethyl sulfoxide solvent molecule is connected to the main molecule via an N—H⋯O hydrogen bond. Weak C—H⋯O hydrogen bonds link the components of the structure into a two-dimensional network parallel to (10-1). Weak intramolecular C—H⋯S hydrogen bonds are also observed. The crystal is an with a ratio of twin components 0.78 (2):0.22 (6).
CCDC reference: 1423184
1. Related literature
For non-covalent interactions, see: Minkin & Minyaev (2001); Bjernemose et al. (2003). For the biological activity of thiazolidines, see: Nazreen et al. (2015); Tripathi et al. (2014). For docking investigations of thiazolidines, see: Sharma et al. (2015); Miyata et al. (2013). For materials applications of thiazolidines, see: Matsui et al. (2010). For the synthesis of related compounds, see: Obydennov et al. (2014).
2. Experimental
2.1. Crystal data
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Data collection: CrysAlis PRO (Agilent, 2013); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007) and PLATON (Spek, 2009); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009) and publCIF (Westrip, 2010); software used to prepare material for publication: OLEX2 and publCIF.
Supporting information
CCDC reference: 1423184
10.1107/S2056989015016850/lh5784sup1.cif
contains datablocks I, exp_300. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989015016850/lh5784Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989015016850/lh5784Isup3.cml
Thiazolidines are an important class of heteroaromatic compounds and have widespread applications from ranging from pharmaceuticals (Tripathi et al., 2014; Nazreen et al., 2015) to materials (Matsui et al., 2010). The structure determined using X-ray crystallography is useful to perform a docking screen, which is frequently used to predict the binding orientation of potential ligands to their targets in order to in turn predict the affinity and activity of the ligands (Miyata et al., 2013; Sharma et al., 2015). Consequently, we have synthesized the title compound and its
is presented herein.The molecular structure of the title compound is shown in Fig. 1. The thioamide group is approximately in the plane of the thiazolidine ring forming a short S1···S2 contact (Minkin & Minyaev, 2001) with a distance of 2.972 (1) Å. This contact is observed for similar compounds containing a five-membered quasi-ring involving S···S interactions (Bjernemose et al., 2003; Obydennov et al., 2014). The p-tolyl group benzene ring and thiazolidine ring form a dihedral angle of 68.60 (14)°. The piperidine ring is in a chair conformation and both the aryl substituents are in equatorial positions. The sum of the bond angles around the thiazolidine ring N3 atom (360.0°) indicates sp2 1). Weak intramolecular C—H···S hydrogen bonds are also observed.
The exocyclic double bonds are in a Z-configuration. In the crystal, the dimethylsulfoxide solvent molecule is connected to the main molecule via an N—H···O hydrogen bond. Weak C—H···O hydrogen bonds link the components of the structure into a two-dimensional network parallel to (10\ (2Z)-2-[(5Z)-5-(3-fluoro-2-(4-phenylpiperidin-1-yl)benzylidene)-\ 4-oxo-3-(p-tolyl)-1,3-thiazolidin-2-ylidene]-N-(p-\ tolyl)ethanethioamide was prepared from (2Z)-N-(4-methylphenyl)-2-[3-(4-methylphenyl)-4-oxo-1,3-\ thiazolidin-2-ylidene]ethanethioamide by the Knoevenagel condensation. To a suspension of (2Z)-N-(4-methylphenyl)-2-[3-(4-methylphenyl)-4-oxo-1,3-\ thiazolidin-2-ylidene]ethanethioamide (248 mg, 0.7 mmol) in n-butanol (10 ml) were added 3-fluoro-2-(4-phenylpiperidin-1-yl)benzaldehyde (397 mg, 1.4 mmol) and piperidine (0.06 ml, 0.7 mmol) at room temperature. The mixture was stirred at refluxe for 12 h. After cooling to 255K the crude product was filtered off, recrystallized from ethanol, washed by cooled ethanol and dried in vacuo. Yield: 126 mg (29%). 1H NMR (400 MHz, DMSO-d6, δ, p.p.m.): 1.68–1.92 (4H, br.m., CH2), 2.26 (1H, s., Me), 2.43 (1H, s., Me), 2.70 (1H, br.m., CH), 3.02–3.20 (2H, br.m., CH2), 3.20–3.32 (2H, br.m., CH2), 6.19 (1H, s., CH=), 7.04–7.66 (15H, m., ArH + CH=), 8.04 (1H, s., ArH), 11.17 (1H, s., NH). Needle-like orange single crystals suitable for X-ray diffraction studies were obtained by slow evaporation of a dimethyl sulfoxide solution of the title compound at room temperature. M.p. 431-433 K.
Data collection: CrysAlis PRO (Agilent, 2013); cell
CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007) and PLATON (Spek, 2009); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009) and publCIF (Westrip, 2010); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) and publCIF (Westrip, 2010).Fig. 1. The molecular structure of the title compound showing 50% probability displacement ellipsoids. |
C37H34FN3OS2·C2H6OS | Dx = 1.335 Mg m−3 |
Mr = 697.92 | Melting point = 160–158 K |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.8539 (5) Å | Cell parameters from 2519 reflections |
b = 9.8671 (5) Å | θ = 2.3–30.2° |
c = 18.1633 (8) Å | µ = 0.26 mm−1 |
β = 100.578 (5)° | T = 150 K |
V = 1736.01 (14) Å3 | Block, orange |
Z = 2 | 0.2 × 0.14 × 0.08 mm |
F(000) = 736 |
Agilent Xcalibur Eos diffractometer | 7519 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 5344 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
Detector resolution: 15.9555 pixels mm-1 | θmax = 30.8°, θmin = 2.1° |
ω scans | h = −13→12 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | k = −14→14 |
Tmin = 0.942, Tmax = 1.000 | l = −25→25 |
9751 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.046 | H-atom parameters constrained |
wR(F2) = 0.089 | w = 1/[σ2(Fo2) + (0.021P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
4992 reflections | Δρmax = 0.63 e Å−3 |
437 parameters | Δρmin = −0.48 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 2527 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.22 (6) |
C37H34FN3OS2·C2H6OS | V = 1736.01 (14) Å3 |
Mr = 697.92 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 9.8539 (5) Å | µ = 0.26 mm−1 |
b = 9.8671 (5) Å | T = 150 K |
c = 18.1633 (8) Å | 0.2 × 0.14 × 0.08 mm |
β = 100.578 (5)° |
Agilent Xcalibur Eos diffractometer | 7519 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | 5344 reflections with I > 2σ(I) |
Tmin = 0.942, Tmax = 1.000 | Rint = 0.029 |
9751 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | H-atom parameters constrained |
wR(F2) = 0.089 | Δρmax = 0.63 e Å−3 |
S = 1.00 | Δρmin = −0.48 e Å−3 |
4992 reflections | Absolute structure: Flack (1983), 2527 Friedel pairs |
437 parameters | Absolute structure parameter: 0.22 (6) |
1 restraint |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.53305 (8) | 0.25119 (8) | 0.25856 (4) | 0.02326 (18) | |
S3 | 0.80859 (11) | 0.72542 (12) | 0.55377 (5) | 0.0473 (3) | |
O2 | 0.5650 (2) | 0.5633 (2) | 0.13469 (12) | 0.0293 (5) | |
F1 | 0.15403 (19) | −0.03590 (19) | −0.04379 (10) | 0.0352 (5) | |
C7 | 0.4153 (3) | 0.1509 (3) | 0.08448 (17) | 0.0211 (7) | |
N2 | 0.2325 (2) | 0.2421 (3) | −0.01238 (13) | 0.0214 (5) | |
N1 | 0.6889 (3) | 0.3429 (3) | 0.50937 (15) | 0.0294 (7) | |
H1 | 0.7187 | 0.4250 | 0.5119 | 0.035* | |
C20 | 0.0297 (3) | 0.5866 (3) | −0.13326 (17) | 0.0220 (7) | |
C2 | 0.6082 (3) | 0.3936 (3) | 0.30804 (18) | 0.0201 (7) | |
C34 | 0.6393 (3) | 0.3019 (3) | 0.43872 (18) | 0.0268 (8) | |
C39 | 0.7442 (3) | 0.1644 (4) | 0.72440 (18) | 0.0252 (8) | |
C29 | 0.8222 (3) | 0.8738 (3) | 0.31806 (17) | 0.0245 (8) | |
C11 | 0.2678 (3) | −0.0075 (3) | 0.00875 (17) | 0.0245 (7) | |
C21 | −0.1030 (3) | 0.6112 (3) | −0.17432 (18) | 0.0278 (8) | |
H21 | −0.1743 | 0.5523 | −0.1692 | 0.033* | |
C12 | 0.3016 (3) | 0.1303 (3) | 0.02578 (17) | 0.0219 (7) | |
C19 | 0.1557 (3) | 0.2225 (3) | −0.08942 (16) | 0.0252 (7) | |
H19A | 0.0671 | 0.1808 | −0.0878 | 0.030* | |
H19B | 0.2070 | 0.1621 | −0.1164 | 0.030* | |
C26 | 0.6885 (3) | 0.6261 (3) | 0.28185 (16) | 0.0192 (7) | |
C10 | 0.3402 (3) | −0.1149 (3) | 0.04386 (18) | 0.0284 (8) | |
H10 | 0.3145 | −0.2032 | 0.0296 | 0.034* | |
C31 | 0.8311 (3) | 0.6293 (3) | 0.30665 (17) | 0.0255 (8) | |
H31 | 0.8822 | 0.5495 | 0.3109 | 0.031* | |
C33 | 0.6496 (3) | 0.4047 (3) | 0.38338 (18) | 0.0243 (7) | |
H33 | 0.6886 | 0.4870 | 0.4012 | 0.029* | |
C24 | 0.1034 (4) | 0.7911 (3) | −0.1875 (2) | 0.0329 (9) | |
H24 | 0.1724 | 0.8537 | −0.1911 | 0.040* | |
O3 | 0.8366 (3) | 0.5875 (3) | 0.52409 (16) | 0.0588 (8) | |
C38 | 0.7181 (4) | 0.0861 (4) | 0.6629 (2) | 0.0407 (10) | |
H38 | 0.7130 | −0.0073 | 0.6689 | 0.049* | |
C17 | 0.0588 (3) | 0.4582 (3) | −0.08805 (17) | 0.0234 (7) | |
H17 | −0.0305 | 0.4185 | −0.0835 | 0.028* | |
C30 | 0.8959 (3) | 0.7534 (4) | 0.32496 (16) | 0.0267 (7) | |
H30 | 0.9908 | 0.7555 | 0.3422 | 0.032* | |
C28 | 0.6801 (3) | 0.8663 (3) | 0.29401 (17) | 0.0245 (7) | |
H28 | 0.6283 | 0.9457 | 0.2897 | 0.029* | |
C18 | 0.1332 (3) | 0.3556 (3) | −0.12984 (17) | 0.0260 (7) | |
H18A | 0.0791 | 0.3408 | −0.1794 | 0.031* | |
H18B | 0.2218 | 0.3926 | −0.1357 | 0.031* | |
C15 | 0.1606 (3) | 0.3354 (3) | 0.02973 (17) | 0.0237 (7) | |
H15A | 0.2128 | 0.3455 | 0.0802 | 0.028* | |
H15B | 0.0706 | 0.2987 | 0.0331 | 0.028* | |
C6 | 0.4630 (3) | 0.2886 (3) | 0.10419 (17) | 0.0209 (7) | |
H6 | 0.4554 | 0.3498 | 0.0647 | 0.025* | |
N3 | 0.6215 (3) | 0.5000 (2) | 0.25863 (14) | 0.0207 (6) | |
C36 | 0.7022 (3) | 0.2793 (3) | 0.58018 (18) | 0.0248 (8) | |
C23 | −0.0257 (4) | 0.8094 (3) | −0.22808 (19) | 0.0303 (8) | |
H23 | −0.0436 | 0.8830 | −0.2604 | 0.036* | |
C22 | −0.1303 (3) | 0.7198 (4) | −0.22178 (18) | 0.0334 (8) | |
H22 | −0.2185 | 0.7329 | −0.2495 | 0.040* | |
C9 | 0.4511 (3) | −0.0914 (3) | 0.10031 (18) | 0.0282 (8) | |
H9 | 0.5014 | −0.1635 | 0.1245 | 0.034* | |
C25 | 0.1329 (3) | 0.6792 (3) | −0.14067 (17) | 0.0285 (8) | |
H25 | 0.2220 | 0.6662 | −0.1142 | 0.034* | |
C16 | 0.1431 (3) | 0.4732 (3) | −0.00841 (17) | 0.0249 (7) | |
H16A | 0.2330 | 0.5112 | −0.0107 | 0.030* | |
H16B | 0.0961 | 0.5344 | 0.0203 | 0.030* | |
C27 | 0.6140 (3) | 0.7448 (4) | 0.27641 (16) | 0.0236 (7) | |
H27 | 0.5187 | 0.7427 | 0.2608 | 0.028* | |
C4 | 0.5671 (3) | 0.4781 (3) | 0.18329 (17) | 0.0212 (7) | |
C41 | 0.7255 (3) | 0.3600 (3) | 0.64298 (18) | 0.0289 (8) | |
H41 | 0.7270 | 0.4537 | 0.6378 | 0.035* | |
C42 | 0.7674 (3) | 0.1067 (4) | 0.80330 (18) | 0.0376 (9) | |
H42A | 0.7368 | 0.0142 | 0.8016 | 0.056* | |
H42B | 0.7162 | 0.1588 | 0.8335 | 0.056* | |
H42C | 0.8639 | 0.1106 | 0.8247 | 0.056* | |
C5 | 0.5160 (3) | 0.3375 (3) | 0.17185 (17) | 0.0191 (7) | |
C37 | 0.6984 (4) | 0.1388 (4) | 0.5902 (2) | 0.0493 (11) | |
H37 | 0.6829 | 0.0811 | 0.5490 | 0.059* | |
C8 | 0.4869 (3) | 0.0401 (3) | 0.12070 (18) | 0.0273 (8) | |
H8 | 0.5607 | 0.0556 | 0.1597 | 0.033* | |
C40 | 0.7468 (4) | 0.3030 (4) | 0.71362 (19) | 0.0304 (8) | |
H40 | 0.7634 | 0.3596 | 0.7552 | 0.036* | |
C43 | 0.6849 (4) | 0.7983 (4) | 0.4815 (2) | 0.0515 (11) | |
H43A | 0.7139 | 0.7859 | 0.4343 | 0.077* | |
H43B | 0.6768 | 0.8934 | 0.4910 | 0.077* | |
H43C | 0.5972 | 0.7552 | 0.4802 | 0.077* | |
C32 | 0.8930 (4) | 1.0061 (3) | 0.33599 (19) | 0.0376 (9) | |
H32A | 0.9678 | 0.9949 | 0.3776 | 0.056* | |
H32B | 0.8285 | 1.0710 | 0.3487 | 0.056* | |
H32C | 0.9284 | 1.0377 | 0.2932 | 0.056* | |
S2 | 0.56650 (10) | 0.15033 (9) | 0.41505 (5) | 0.0337 (2) | |
C44 | 0.9535 (4) | 0.8225 (4) | 0.5416 (3) | 0.0622 (13) | |
H44A | 1.0315 | 0.7976 | 0.5790 | 0.093* | |
H44B | 0.9337 | 0.9170 | 0.5464 | 0.093* | |
H44C | 0.9738 | 0.8056 | 0.4927 | 0.093* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0272 (4) | 0.0181 (4) | 0.0226 (4) | −0.0025 (4) | −0.0007 (3) | 0.0005 (4) |
S3 | 0.0589 (7) | 0.0459 (7) | 0.0323 (5) | −0.0111 (6) | −0.0045 (4) | 0.0061 (5) |
O2 | 0.0355 (14) | 0.0227 (13) | 0.0269 (13) | −0.0079 (11) | −0.0017 (10) | 0.0060 (11) |
F1 | 0.0356 (12) | 0.0279 (11) | 0.0369 (12) | −0.0098 (9) | −0.0068 (9) | −0.0063 (10) |
C7 | 0.0237 (16) | 0.0191 (16) | 0.0204 (16) | 0.0005 (15) | 0.0037 (13) | −0.0021 (15) |
N2 | 0.0234 (13) | 0.0218 (14) | 0.0178 (13) | 0.0016 (13) | 0.0006 (10) | −0.0025 (13) |
N1 | 0.0438 (18) | 0.0172 (15) | 0.0239 (15) | −0.0033 (13) | −0.0025 (13) | −0.0005 (13) |
C20 | 0.0260 (17) | 0.0236 (18) | 0.0174 (16) | 0.0007 (15) | 0.0063 (13) | −0.0060 (15) |
C2 | 0.0161 (15) | 0.0152 (16) | 0.0278 (18) | 0.0022 (13) | 0.0010 (13) | −0.0025 (15) |
C34 | 0.0283 (18) | 0.0236 (17) | 0.0261 (19) | 0.0015 (15) | −0.0019 (14) | 0.0015 (16) |
C39 | 0.0192 (16) | 0.030 (2) | 0.0256 (18) | 0.0035 (16) | 0.0018 (13) | 0.0053 (17) |
C29 | 0.0332 (19) | 0.0246 (19) | 0.0156 (16) | −0.0063 (15) | 0.0038 (14) | −0.0011 (16) |
C11 | 0.0261 (18) | 0.0248 (19) | 0.0214 (17) | −0.0067 (15) | 0.0009 (14) | −0.0031 (16) |
C21 | 0.0260 (18) | 0.028 (2) | 0.0291 (19) | −0.0013 (15) | 0.0045 (14) | −0.0018 (16) |
C12 | 0.0230 (16) | 0.0230 (18) | 0.0202 (16) | 0.0000 (14) | 0.0056 (13) | −0.0017 (15) |
C19 | 0.0303 (17) | 0.0243 (19) | 0.0187 (16) | 0.0038 (15) | −0.0013 (13) | −0.0080 (16) |
C26 | 0.0219 (16) | 0.0203 (18) | 0.0142 (15) | −0.0052 (14) | 0.0000 (12) | 0.0002 (14) |
C10 | 0.039 (2) | 0.0132 (16) | 0.033 (2) | −0.0067 (15) | 0.0070 (16) | −0.0013 (16) |
C31 | 0.0233 (17) | 0.0248 (19) | 0.0282 (18) | 0.0055 (15) | 0.0043 (14) | 0.0000 (16) |
C33 | 0.0238 (18) | 0.0196 (17) | 0.0277 (18) | −0.0025 (14) | 0.0001 (14) | −0.0026 (15) |
C24 | 0.034 (2) | 0.027 (2) | 0.039 (2) | −0.0075 (16) | 0.0115 (17) | 0.0002 (18) |
O3 | 0.0551 (18) | 0.0225 (15) | 0.086 (2) | −0.0061 (13) | −0.0216 (15) | −0.0003 (15) |
C38 | 0.058 (3) | 0.0203 (19) | 0.036 (2) | 0.0052 (18) | −0.0114 (18) | 0.0069 (18) |
C17 | 0.0219 (17) | 0.0264 (18) | 0.0206 (17) | 0.0001 (15) | 0.0007 (13) | −0.0021 (16) |
C30 | 0.0173 (15) | 0.033 (2) | 0.0284 (17) | −0.0060 (16) | 0.0008 (12) | −0.0008 (18) |
C28 | 0.0293 (19) | 0.0207 (18) | 0.0222 (17) | −0.0009 (15) | 0.0011 (14) | 0.0017 (15) |
C18 | 0.0311 (18) | 0.0282 (19) | 0.0170 (16) | 0.0015 (15) | −0.0004 (14) | −0.0032 (15) |
C15 | 0.0258 (18) | 0.0267 (19) | 0.0183 (16) | 0.0031 (15) | 0.0035 (13) | −0.0015 (15) |
C6 | 0.0193 (16) | 0.0212 (18) | 0.0224 (17) | 0.0007 (13) | 0.0038 (13) | 0.0057 (15) |
N3 | 0.0210 (13) | 0.0174 (14) | 0.0221 (14) | −0.0006 (11) | −0.0004 (11) | 0.0001 (12) |
C36 | 0.0294 (18) | 0.0213 (19) | 0.0208 (17) | −0.0012 (14) | −0.0025 (13) | 0.0010 (15) |
C23 | 0.033 (2) | 0.0235 (18) | 0.035 (2) | 0.0049 (16) | 0.0070 (16) | 0.0063 (16) |
C22 | 0.0300 (18) | 0.039 (2) | 0.0292 (18) | 0.0072 (17) | 0.0002 (14) | 0.0059 (19) |
C9 | 0.033 (2) | 0.0239 (19) | 0.0266 (19) | −0.0006 (16) | 0.0029 (15) | 0.0031 (16) |
C25 | 0.0259 (18) | 0.030 (2) | 0.0282 (18) | 0.0019 (15) | 0.0018 (14) | −0.0015 (17) |
C16 | 0.0289 (18) | 0.0191 (17) | 0.0261 (18) | 0.0022 (15) | 0.0034 (14) | −0.0020 (15) |
C27 | 0.0194 (15) | 0.0254 (17) | 0.0245 (16) | −0.0014 (16) | 0.0002 (12) | 0.0009 (17) |
C4 | 0.0154 (15) | 0.0242 (18) | 0.0226 (17) | −0.0004 (14) | 0.0000 (13) | 0.0011 (16) |
C41 | 0.039 (2) | 0.0189 (18) | 0.0287 (19) | −0.0034 (16) | 0.0064 (16) | −0.0031 (16) |
C42 | 0.035 (2) | 0.042 (2) | 0.036 (2) | 0.0032 (17) | 0.0043 (17) | 0.009 (2) |
C5 | 0.0170 (15) | 0.0185 (17) | 0.0212 (17) | 0.0024 (13) | 0.0022 (12) | 0.0019 (14) |
C37 | 0.082 (3) | 0.030 (2) | 0.029 (2) | 0.011 (2) | −0.009 (2) | −0.008 (2) |
C8 | 0.0299 (19) | 0.0206 (18) | 0.0283 (19) | −0.0017 (15) | −0.0030 (15) | 0.0034 (16) |
C40 | 0.040 (2) | 0.0290 (19) | 0.0216 (18) | −0.0070 (17) | 0.0050 (15) | −0.0071 (17) |
C43 | 0.064 (3) | 0.041 (3) | 0.047 (3) | 0.011 (2) | 0.001 (2) | 0.008 (2) |
C32 | 0.048 (2) | 0.029 (2) | 0.035 (2) | −0.0099 (17) | 0.0035 (18) | −0.0025 (18) |
S2 | 0.0512 (6) | 0.0236 (5) | 0.0245 (5) | −0.0075 (5) | 0.0020 (4) | −0.0012 (4) |
C44 | 0.060 (3) | 0.044 (3) | 0.075 (3) | −0.020 (2) | −0.006 (2) | 0.002 (3) |
S1—C2 | 1.757 (3) | C24—H24 | 0.9300 |
S1—C5 | 1.771 (3) | C38—C37 | 1.399 (5) |
S3—O3 | 1.508 (3) | C38—H38 | 0.9300 |
S3—C44 | 1.766 (4) | C17—C18 | 1.531 (4) |
S3—C43 | 1.771 (4) | C17—C16 | 1.537 (4) |
O2—C4 | 1.217 (3) | C17—H17 | 0.9800 |
F1—C11 | 1.361 (3) | C30—H30 | 0.9300 |
C7—C8 | 1.398 (4) | C28—C27 | 1.374 (4) |
C7—C12 | 1.413 (4) | C28—H28 | 0.9300 |
C7—C6 | 1.460 (4) | C18—H18A | 0.9700 |
N2—C12 | 1.410 (4) | C18—H18B | 0.9700 |
N2—C15 | 1.461 (4) | C15—C16 | 1.521 (4) |
N2—C19 | 1.476 (3) | C15—H15A | 0.9700 |
N1—C34 | 1.349 (4) | C15—H15B | 0.9700 |
N1—C36 | 1.416 (4) | C6—C5 | 1.334 (4) |
N1—H1 | 0.8600 | C6—H6 | 0.9300 |
C20—C25 | 1.392 (4) | N3—C4 | 1.392 (4) |
C20—C21 | 1.402 (4) | C36—C41 | 1.376 (4) |
C20—C17 | 1.509 (4) | C36—C37 | 1.400 (5) |
C2—C33 | 1.358 (4) | C23—C22 | 1.378 (4) |
C2—N3 | 1.402 (4) | C23—H23 | 0.9300 |
C34—C33 | 1.444 (4) | C22—H22 | 0.9300 |
C34—S2 | 1.680 (3) | C9—C8 | 1.377 (4) |
C39—C38 | 1.344 (5) | C9—H9 | 0.9300 |
C39—C40 | 1.382 (4) | C25—H25 | 0.9300 |
C39—C42 | 1.520 (4) | C16—H16A | 0.9700 |
C29—C30 | 1.387 (4) | C16—H16B | 0.9700 |
C29—C28 | 1.390 (4) | C27—H27 | 0.9300 |
C29—C32 | 1.487 (4) | C4—C5 | 1.477 (4) |
C11—C10 | 1.368 (4) | C41—C40 | 1.381 (4) |
C11—C12 | 1.420 (4) | C41—H41 | 0.9300 |
C21—C22 | 1.370 (4) | C42—H42A | 0.9600 |
C21—H21 | 0.9300 | C42—H42B | 0.9600 |
C19—C18 | 1.501 (4) | C42—H42C | 0.9600 |
C19—H19A | 0.9700 | C37—H37 | 0.9300 |
C19—H19B | 0.9700 | C8—H8 | 0.9300 |
C26—C27 | 1.376 (4) | C40—H40 | 0.9300 |
C26—C31 | 1.395 (4) | C43—H43A | 0.9600 |
C26—N3 | 1.436 (4) | C43—H43B | 0.9600 |
C10—C9 | 1.374 (4) | C43—H43C | 0.9600 |
C10—H10 | 0.9300 | C32—H32A | 0.9600 |
C31—C30 | 1.393 (5) | C32—H32B | 0.9600 |
C31—H31 | 0.9300 | C32—H32C | 0.9600 |
C33—H33 | 0.9300 | C44—H44A | 0.9600 |
C24—C23 | 1.361 (5) | C44—H44B | 0.9600 |
C24—C25 | 1.391 (4) | C44—H44C | 0.9600 |
C2—S1—C5 | 91.86 (15) | C19—C18—C17 | 112.1 (2) |
O3—S3—C44 | 103.86 (19) | C19—C18—H18A | 109.2 |
O3—S3—C43 | 104.35 (17) | C17—C18—H18A | 109.2 |
C44—S3—C43 | 98.6 (2) | C19—C18—H18B | 109.2 |
C8—C7—C12 | 120.3 (3) | C17—C18—H18B | 109.2 |
C8—C7—C6 | 120.0 (3) | H18A—C18—H18B | 107.9 |
C12—C7—C6 | 119.6 (3) | N2—C15—C16 | 110.5 (2) |
C12—N2—C15 | 118.2 (2) | N2—C15—H15A | 109.6 |
C12—N2—C19 | 118.7 (3) | C16—C15—H15A | 109.6 |
C15—N2—C19 | 111.4 (2) | N2—C15—H15B | 109.6 |
C34—N1—C36 | 133.5 (3) | C16—C15—H15B | 109.6 |
C34—N1—H1 | 113.3 | H15A—C15—H15B | 108.1 |
C36—N1—H1 | 113.3 | C5—C6—C7 | 128.0 (3) |
C25—C20—C21 | 117.5 (3) | C5—C6—H6 | 116.0 |
C25—C20—C17 | 122.3 (3) | C7—C6—H6 | 116.0 |
C21—C20—C17 | 120.0 (3) | C4—N3—C2 | 116.7 (3) |
C33—C2—N3 | 122.6 (3) | C4—N3—C26 | 119.8 (3) |
C33—C2—S1 | 126.9 (2) | C2—N3—C26 | 123.5 (3) |
N3—C2—S1 | 110.6 (2) | C41—C36—C37 | 118.0 (3) |
N1—C34—C33 | 113.1 (3) | C41—C36—N1 | 118.0 (3) |
N1—C34—S2 | 125.0 (2) | C37—C36—N1 | 123.9 (3) |
C33—C34—S2 | 121.9 (3) | C24—C23—C22 | 120.6 (3) |
C38—C39—C40 | 117.2 (3) | C24—C23—H23 | 119.7 |
C38—C39—C42 | 122.7 (3) | C22—C23—H23 | 119.7 |
C40—C39—C42 | 120.0 (3) | C21—C22—C23 | 119.3 (3) |
C30—C29—C28 | 117.6 (3) | C21—C22—H22 | 120.3 |
C30—C29—C32 | 121.0 (3) | C23—C22—H22 | 120.3 |
C28—C29—C32 | 121.4 (3) | C10—C9—C8 | 119.3 (3) |
F1—C11—C10 | 117.3 (3) | C10—C9—H9 | 120.4 |
F1—C11—C12 | 118.7 (3) | C8—C9—H9 | 120.4 |
C10—C11—C12 | 124.0 (3) | C24—C25—C20 | 120.4 (3) |
C22—C21—C20 | 121.8 (3) | C24—C25—H25 | 119.8 |
C22—C21—H21 | 119.1 | C20—C25—H25 | 119.8 |
C20—C21—H21 | 119.1 | C15—C16—C17 | 109.8 (3) |
N2—C12—C7 | 120.2 (3) | C15—C16—H16A | 109.7 |
N2—C12—C11 | 124.7 (3) | C17—C16—H16A | 109.7 |
C7—C12—C11 | 115.1 (3) | C15—C16—H16B | 109.7 |
N2—C19—C18 | 110.7 (3) | C17—C16—H16B | 109.7 |
N2—C19—H19A | 109.5 | H16A—C16—H16B | 108.2 |
C18—C19—H19A | 109.5 | C28—C27—C26 | 120.1 (3) |
N2—C19—H19B | 109.5 | C28—C27—H27 | 119.9 |
C18—C19—H19B | 109.5 | C26—C27—H27 | 119.9 |
H19A—C19—H19B | 108.1 | O2—C4—N3 | 123.9 (3) |
C27—C26—C31 | 119.8 (3) | O2—C4—C5 | 125.9 (3) |
C27—C26—N3 | 120.4 (3) | N3—C4—C5 | 110.1 (3) |
C31—C26—N3 | 119.7 (3) | C36—C41—C40 | 120.5 (3) |
C11—C10—C9 | 119.5 (3) | C36—C41—H41 | 119.7 |
C11—C10—H10 | 120.3 | C40—C41—H41 | 119.7 |
C9—C10—H10 | 120.3 | C39—C42—H42A | 109.5 |
C30—C31—C26 | 119.2 (3) | C39—C42—H42B | 109.5 |
C30—C31—H31 | 120.4 | H42A—C42—H42B | 109.5 |
C26—C31—H31 | 120.4 | C39—C42—H42C | 109.5 |
C2—C33—C34 | 126.7 (3) | H42A—C42—H42C | 109.5 |
C2—C33—H33 | 116.6 | H42B—C42—H42C | 109.5 |
C34—C33—H33 | 116.6 | C6—C5—C4 | 122.3 (3) |
C23—C24—C25 | 120.4 (3) | C6—C5—S1 | 127.0 (2) |
C23—C24—H24 | 119.8 | C4—C5—S1 | 110.6 (2) |
C25—C24—H24 | 119.8 | C38—C37—C36 | 119.3 (3) |
C39—C38—C37 | 122.9 (3) | C38—C37—H37 | 120.4 |
C39—C38—H38 | 118.6 | C36—C37—H37 | 120.4 |
C37—C38—H38 | 118.6 | C9—C8—C7 | 121.9 (3) |
C20—C17—C18 | 110.3 (2) | C9—C8—H8 | 119.1 |
C20—C17—C16 | 116.6 (3) | C7—C8—H8 | 119.1 |
C18—C17—C16 | 107.7 (2) | C41—C40—C39 | 122.1 (3) |
C20—C17—H17 | 107.3 | C41—C40—H40 | 119.0 |
C18—C17—H17 | 107.3 | C39—C40—H40 | 119.0 |
C16—C17—H17 | 107.3 | C29—C32—H32A | 109.5 |
C29—C30—C31 | 121.5 (3) | C29—C32—H32B | 109.5 |
C29—C30—H30 | 119.3 | H32A—C32—H32B | 109.5 |
C31—C30—H30 | 119.3 | C29—C32—H32C | 109.5 |
C27—C28—C29 | 121.8 (3) | H32A—C32—H32C | 109.5 |
C27—C28—H28 | 119.1 | H32B—C32—H32C | 109.5 |
C29—C28—H28 | 119.1 | ||
C5—S1—C2—C33 | 178.6 (3) | C33—C2—N3—C4 | −176.1 (3) |
C5—S1—C2—N3 | −1.4 (2) | S1—C2—N3—C4 | 3.9 (3) |
C36—N1—C34—C33 | −179.1 (3) | C33—C2—N3—C26 | 4.7 (4) |
C36—N1—C34—S2 | 3.2 (5) | S1—C2—N3—C26 | −175.3 (2) |
C25—C20—C21—C22 | 1.8 (4) | C27—C26—N3—C4 | 66.9 (4) |
C17—C20—C21—C22 | −173.5 (3) | C31—C26—N3—C4 | −110.0 (3) |
C15—N2—C12—C7 | −64.4 (4) | C27—C26—N3—C2 | −113.9 (3) |
C19—N2—C12—C7 | 155.6 (3) | C31—C26—N3—C2 | 69.2 (4) |
C15—N2—C12—C11 | 117.2 (3) | C34—N1—C36—C41 | −164.0 (3) |
C19—N2—C12—C11 | −22.8 (4) | C34—N1—C36—C37 | 18.6 (6) |
C8—C7—C12—N2 | −177.8 (3) | C25—C24—C23—C22 | 2.0 (5) |
C6—C7—C12—N2 | −1.4 (4) | C20—C21—C22—C23 | −1.6 (5) |
C8—C7—C12—C11 | 0.7 (4) | C24—C23—C22—C21 | −0.3 (5) |
C6—C7—C12—C11 | 177.1 (3) | C11—C10—C9—C8 | 0.3 (5) |
F1—C11—C12—N2 | −5.7 (4) | C23—C24—C25—C20 | −1.8 (5) |
C10—C11—C12—N2 | 176.6 (3) | C21—C20—C25—C24 | −0.1 (4) |
F1—C11—C12—C7 | 175.8 (2) | C17—C20—C25—C24 | 175.1 (3) |
C10—C11—C12—C7 | −1.9 (5) | N2—C15—C16—C17 | 59.9 (3) |
C12—N2—C19—C18 | −159.8 (2) | C20—C17—C16—C15 | 178.9 (2) |
C15—N2—C19—C18 | 57.7 (3) | C18—C17—C16—C15 | −56.6 (3) |
F1—C11—C10—C9 | −176.3 (3) | C29—C28—C27—C26 | −0.5 (4) |
C12—C11—C10—C9 | 1.4 (5) | C31—C26—C27—C28 | 1.2 (4) |
C27—C26—C31—C30 | −0.5 (4) | N3—C26—C27—C28 | −175.7 (3) |
N3—C26—C31—C30 | 176.4 (3) | C2—N3—C4—O2 | 176.2 (3) |
N3—C2—C33—C34 | 179.5 (3) | C26—N3—C4—O2 | −4.6 (4) |
S1—C2—C33—C34 | −0.6 (5) | C2—N3—C4—C5 | −4.8 (3) |
N1—C34—C33—C2 | −179.8 (3) | C26—N3—C4—C5 | 174.5 (2) |
S2—C34—C33—C2 | −2.0 (4) | C37—C36—C41—C40 | 1.1 (5) |
C40—C39—C38—C37 | 2.0 (5) | N1—C36—C41—C40 | −176.5 (3) |
C42—C39—C38—C37 | −179.2 (3) | C7—C6—C5—C4 | 176.7 (3) |
C25—C20—C17—C18 | −73.6 (4) | C7—C6—C5—S1 | −4.7 (5) |
C21—C20—C17—C18 | 101.5 (3) | O2—C4—C5—C6 | 1.3 (5) |
C25—C20—C17—C16 | 49.6 (4) | N3—C4—C5—C6 | −177.7 (3) |
C21—C20—C17—C16 | −135.3 (3) | O2—C4—C5—S1 | −177.6 (2) |
C28—C29—C30—C31 | 1.7 (4) | N3—C4—C5—S1 | 3.5 (3) |
C32—C29—C30—C31 | −178.5 (3) | C2—S1—C5—C6 | −179.9 (3) |
C26—C31—C30—C29 | −0.9 (4) | C2—S1—C5—C4 | −1.2 (2) |
C30—C29—C28—C27 | −1.0 (4) | C39—C38—C37—C36 | −1.7 (6) |
C32—C29—C28—C27 | 179.2 (3) | C41—C36—C37—C38 | 0.0 (6) |
N2—C19—C18—C17 | −56.4 (3) | N1—C36—C37—C38 | 177.4 (3) |
C20—C17—C18—C19 | −176.0 (3) | C10—C9—C8—C7 | −1.4 (5) |
C16—C17—C18—C19 | 55.8 (3) | C12—C7—C8—C9 | 0.9 (5) |
C12—N2—C15—C16 | 157.4 (3) | C6—C7—C8—C9 | −175.5 (3) |
C19—N2—C15—C16 | −59.9 (3) | C36—C41—C40—C39 | −0.7 (6) |
C8—C7—C6—C5 | −38.0 (5) | C38—C39—C40—C41 | −0.8 (5) |
C12—C7—C6—C5 | 145.6 (3) | C42—C39—C40—C41 | −179.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3 | 0.86 | 1.97 | 2.806 (4) | 164 |
C8—H8···S1 | 0.93 | 2.68 | 3.224 (3) | 118 |
C19—H19B···O2i | 0.97 | 2.53 | 3.398 (4) | 149 |
C32—H32A···O3ii | 0.96 | 2.54 | 3.423 (5) | 152 |
C37—H37···S2 | 0.93 | 2.58 | 3.210 (4) | 125 |
Symmetry codes: (i) −x+1, y−1/2, −z; (ii) −x+2, y+1/2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3 | 0.86 | 1.97 | 2.806 (4) | 164 |
C8—H8···S1 | 0.93 | 2.68 | 3.224 (3) | 118 |
C19—H19B···O2i | 0.97 | 2.53 | 3.398 (4) | 149 |
C32—H32A···O3ii | 0.96 | 2.54 | 3.423 (5) | 152 |
C37—H37···S2 | 0.93 | 2.58 | 3.210 (4) | 125 |
Symmetry codes: (i) −x+1, y−1/2, −z; (ii) −x+2, y+1/2, −z+1. |
Acknowledgements
We thank State task Ministry of Education and Science of the Russian Federation No. 4.560.2014-K
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