research communications
Crystal structures of two (Z)-2-(4-oxo-1,3-thiazolidin-2-ylidene)acetamides
aUral Federal University, Mira 19 Ekaterinburg 620002, Russian Federation, and b22 Sofia Kovalevskaya str., Ekaterinburg, 620990, Russian Federation
*Correspondence e-mail: k.l.obydennov@urfu.ru
The crystal structures of two (oxothiazolidin-2-ylidene)acetamides, namely (Z)-2-[2-(morpholin-4-yl)-2-oxoethylidene]thiazolidin-4-one, C9H12N2O3S, (I), and (Z)-N-(4-methoxyphenyl)-2-(4-oxothiazolidin-2-ylidene)acetamide, C12H12N2O3S, (II), are described and compared with a related structure. The Z conformation was observed for both the compounds. In (I), the morpholin-4-yl ring has a chair conformation and its mean plane is inclined to the thiazolidine ring mean plane by 37.12 (12)°. In (II), the benzene ring is inclined to the mean plane of the thiazolidine ring by 20.34 (14)°. In the crystal of (I), molecules are linked by N—H⋯O hydrogen bonds, forming C(6) chains along the b-axis direction. The edge-to-edge arrangement of the molecules results in short C—H⋯O and C—H⋯S interactions, which consolidate the chain into a ribbon-like structure. In the crystal of (II), two N—H⋯O hydrogen bonds result in the formation of C(8) chains along the b-axis direction and C(6) chains along the c-axis direction. The combination of these interactions leads to the formation of layers parallel to the bc plane, enclosing R44(28) rings involving four molecules.
Keywords: crystal structure; thiazolidine; thiazolidin-4-one; acetamide; hydrogen bonding.
1. Chemical context
Thiazolidine derivatives are of great biological importance due to their antidiabetic (Rizos et al., 2016) and antibacterial (Har & Solensky, 2017) activity. One such compound, namely (Z)-N-(2-chloro-6-methylphenyl)-2-(3-methyl-4-oxo-1,3-thiazolidin-2-ylidene)acetamide (ralitoline), has been found to be effective in a preclinical anticonvulsant evaluation (Löscher & Schmidt, 1994). In view of the importance of 2-(4-oxothiazolidin-2-ylidene)acetamides, the title compounds, (I) and (II), were synthesized and we report herein on their crystal structures. To date, the of only one such compound, viz. (Z)-2-cyano-2-(4-oxo-3-phenyl-1,3-thiazolidin-2-ylidene)-N-phenylacetamide, (III), has been reported (George, 2012).
2. Structural commentary
The molecular structures of the title compounds, (I) and (II), are illustrated in Figs. 1 and 2, respectively. Both compounds crystallize in the monoclinic P21/c. The Z conformation about the C8=C9 bond is observed for both compounds and favours S⋯O contacts of 2.6902 (18) and 2.738 (3) Å in (I) and (II), respectively. The morpholine ring in compound (I) adopts a chair conformation. The twist angle between the thiazolidine (S1/N2/C9–C11) and amide mean planes (O1/N1/C7/C8) is 10.71 (10)° in (I) and 2.36 (14)° in (II). In (II), the benzene ring plane is inclined to the mean plane of the thiazolidine ring by 20.60 (12)°. The bond lengths and angles in both compounds are similar to those observed for compound (III), mentioned above.
3. Supramolecular features
In the crystal of (I), molecules are linked by N—H⋯O hydrogen bonds forming C(6) chains running parallel to the a-axis direction (Table 1 and Fig. 3). The dihedral angle between thiazolidine mean planes is 6.12 (7)°. There are three non-classical C2—H2A⋯S1i, C5—H5B⋯O3ii and C6—H6B⋯O3iii (Table 1) hydrogen bonds present, linking molecules to form ribbons propagating along [100]; Table 1 and Fig. 3.
In crystal of (II), both amide moieties participate in the formation of N—H⋯O hydrogen bonds (see Table 2). These two types of N—H⋯O hydrogen bonds give rise to the formation of two independent C(8) and C(6) chains, running parallel to the b- and c-axes, respectively (see Figs. 4 and 5). Here, the dihedral angle between the thiazolidine mean planes in the N1—H1⋯O3i and N2—H2⋯O2ii motifs is 79.21 (16)°. The combination of these chain motifs generates a two-dimensional network lying parallel to the bc plane. Each molecule acts as both a double donor and a double acceptor of N—H⋯O hydrogen bonds. The molecules of (II) are linked into aggregated R44(28) tetramers, which serve as the building blocks of the layers (see Fig. 6).
4. Database survey
A search of the Cambridge Structural Database (Version 5.38; Groom et al., 2016) for the 2-methylene-1,3-thiazolidin-4-one gave nine hits. The compound that most closely resembles the title compounds is 2-cyano-2-(4-oxo-3-phenyl-1,3-thiazolidin-2-ylidene)-N-phenylacetamide (III) (NEYGUV; George, 2012). Here the amide mean plane [C—C(=O)—N] is inclined to the mean plane of the thiazolidine ring by 5.09 (16)°, compared to 2.36 (14)° in (II). The benzene ring is inclined to the to the mean plane of the thiazolidine ring by 38.10 (15)° compared to 20.34 (14)° in (II). In the crystal of (III), molecules are linked by N—H⋯O hydrogen bonds, forming chains along the [010] direction. It should be noted that no crystal structures of 2-methylene-1,3-thiazolidin-4-one derivatives without a substituent at the N atom in position 3 of the thiazolidine ring were found.
5. Synthesis and crystallization
Thiazolidinones (I) and (II) were prepared from cyanoacetamides (see Fig. 7), by a previously described method (Obydennov et al., 2017). Pyridine was added dropwise with stirring to cyanoacetamide (15 mmol) in a round-bottom flask until complete dissolution of the cyanoacetamide. 4-Dimethylaminopyridine (DMAP) (18 mg, 0.15 mmol) for (I), and mercaptoacetic acid (3.2 ml, 46 mmol) for (II), were added and the mixtures were refluxed for 12 h. They were then cooled to room temperature and diluted with a 0.5 N HCl solution (5 ml). The precipitates formed of the 1,3-thiazolidinones, were filtered off. The crude products were additionally purified by refluxing a suspension of the thiazolidine in MeCN, followed by hot filtration. Colourless crystals of compounds (I) and (II) were obtained by slow evaporation of the respective compound in a solution of DMSO.
(Z)-2-[2-(Morpholin-4-yl)-2-oxoethylidene]-1,3-thiazolidin-4-one (I). Yield 1.54 g (45%), white powder, m.p. 503–505 K. 1H NMR spectrum, δ, p.p.m. (J, Hz): 3.42 (4H, t, 4.8 Hz, CH2); 3.54 (2H, s, CH2); 3.57 (4H, t, 4.8 Hz, CH2); 5.83 (1H, s, CH); 11.25 (1H, s, NH).
(Z)-N-(4-Methoxyphenyl)-2-(4-oxo-1,3-thiazolidin-2-ylidene)acetamide (II). Yield 2.85 g (72%), white powder, m.p. 534–536 K. (Obydennov et al., 2017). Elemental analysis for C12H12N2O3S; found, %: C 54.31; H 4.67; N 10.72; calculated, %: C 54.53; H 4.58; N 10.60.
6. Refinement
Crystal data, data collection and structure . For both compounds, the hydrogen atoms were included in calculated positions and refined using the riding model: C—H = 0.93–0.97 Å with Uiso(H) = 1.5Ueq(C-methyl) and 1.2Ueq(C) for other C-bound H atoms. The NH H atoms were located in difference-Fourier maps and freely refined.
details are summarized in Table 3
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Supporting information
https://doi.org/10.1107/S2056989017016061/su5403sup1.cif
contains datablocks Global, II, I. DOI:Supporting information file. DOI: https://doi.org/10.1107/S2056989017016061/su5403Isup2.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989017016061/su5403IIsup3.cml
Data collection: CrysAlis PRO (Agilent, 2013) for (I); CrysAlis CCD (Oxford Diffraction, 2006) for (II). Cell
CrysAlis PRO (Agilent, 2013) for (I); CrysAlis RED (Oxford Diffraction, 2006) for (II). Data reduction: CrysAlis PRO (Agilent, 2013) for (I); CrysAlis RED (Oxford Diffraction, 2006) for (II). For both structures, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008). Molecular graphics: OLEX (Dolomanov et al., 2009) for (I); SHELXTL (Sheldrick, 2008) for (II). Software used to prepare material for publication: PLATON (Spek, 2009), OLEX (Dolomanov et al., 2009) and publCIF (Westrip, 2010) for (I); SHELXTL (Sheldrick, 2008) for (II).C9H12N2O3S | F(000) = 480 |
Mr = 228.27 | Dx = 1.479 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.7107 Å |
a = 9.9740 (4) Å | Cell parameters from 1828 reflections |
b = 11.2175 (4) Å | θ = 2.8–30.1° |
c = 9.3155 (4) Å | µ = 0.30 mm−1 |
β = 100.389 (4)° | T = 295 K |
V = 1025.16 (7) Å3 | Prism, colourless |
Z = 4 | 0.25 × 0.2 × 0.15 mm |
Agilent Xcalibur Eos diffractometer | 2777 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2161 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
Detector resolution: 15.9555 pixels mm-1 | θmax = 30.9°, θmin = 2.8° |
ω scans | h = −14→8 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | k = −12→15 |
Tmin = 0.924, Tmax = 1.000 | l = −8→12 |
5512 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.154 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.1P)2 + 0.1P] where P = (Fo2 + 2Fc2)/3 |
2777 reflections | (Δ/σ)max = 0.001 |
151 parameters | Δρmax = 0.47 e Å−3 |
0 restraints | Δρmin = −0.24 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. |
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 > 2sigma(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 | 0.41099 (5) | 0.19996 (4) | 0.86944 (5) | 0.04126 (18) | |
O1 | 0.60365 (15) | 0.17462 (13) | 0.70341 (18) | 0.0530 (4) | |
O3 | 0.20314 (15) | 0.45139 (14) | 1.00948 (17) | 0.0587 (4) | |
O2 | 1.01954 (17) | 0.35357 (18) | 0.6141 (3) | 0.0846 (6) | |
N2 | 0.37439 (16) | 0.42790 (15) | 0.87892 (17) | 0.0385 (3) | |
N1 | 0.74687 (16) | 0.31439 (15) | 0.6416 (2) | 0.0475 (4) | |
C9 | 0.45545 (16) | 0.34471 (15) | 0.82632 (17) | 0.0331 (3) | |
C11 | 0.27952 (17) | 0.38781 (17) | 0.95594 (19) | 0.0385 (4) | |
C7 | 0.63595 (18) | 0.28193 (17) | 0.6972 (2) | 0.0394 (4) | |
C8 | 0.55522 (18) | 0.37426 (17) | 0.7520 (2) | 0.0393 (4) | |
H8 | 0.572 (2) | 0.449 (2) | 0.737 (2) | 0.047* | |
C2 | 0.7968 (2) | 0.43485 (19) | 0.6280 (3) | 0.0591 (6) | |
H2A | 0.7513 | 0.4892 | 0.6844 | 0.071* | |
H2B | 0.7764 | 0.4595 | 0.5266 | 0.071* | |
C10 | 0.2832 (2) | 0.25413 (19) | 0.9676 (2) | 0.0441 (4) | |
C6 | 0.8258 (2) | 0.2254 (2) | 0.5779 (3) | 0.0652 (7) | |
H6A | 0.8106 | 0.2352 | 0.4728 | 0.078* | |
H6B | 0.7957 | 0.1461 | 0.5990 | 0.078* | |
C3 | 0.9469 (3) | 0.4400 (3) | 0.6813 (4) | 0.0813 (9) | |
H3A | 0.9797 | 0.5188 | 0.6624 | 0.098* | |
H3B | 0.9652 | 0.4275 | 0.7861 | 0.098* | |
C5 | 0.9720 (2) | 0.2383 (2) | 0.6379 (3) | 0.0647 (6) | |
H5A | 0.9876 | 0.2223 | 0.7419 | 0.078* | |
H5B | 1.0231 | 0.1802 | 0.5925 | 0.078* | |
H10A | 0.302 (3) | 0.224 (3) | 1.070 (3) | 0.075 (8)* | |
H10B | 0.195 (4) | 0.232 (3) | 0.933 (3) | 0.089 (10)* | |
H2 | 0.377 (3) | 0.498 (3) | 0.869 (2) | 0.060 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0494 (3) | 0.0229 (3) | 0.0547 (3) | −0.00327 (18) | 0.0178 (2) | −0.00108 (17) |
O1 | 0.0573 (8) | 0.0254 (7) | 0.0828 (10) | −0.0052 (6) | 0.0301 (7) | −0.0098 (6) |
O3 | 0.0605 (9) | 0.0382 (8) | 0.0881 (10) | 0.0025 (7) | 0.0422 (8) | 0.0000 (7) |
O2 | 0.0595 (10) | 0.0483 (11) | 0.1621 (18) | −0.0058 (8) | 0.0631 (11) | −0.0175 (12) |
N2 | 0.0387 (7) | 0.0234 (8) | 0.0568 (9) | −0.0013 (6) | 0.0173 (6) | −0.0008 (6) |
N1 | 0.0405 (8) | 0.0293 (9) | 0.0774 (11) | −0.0024 (6) | 0.0237 (7) | −0.0110 (7) |
C9 | 0.0346 (8) | 0.0226 (8) | 0.0419 (8) | −0.0024 (6) | 0.0067 (6) | −0.0032 (6) |
C11 | 0.0377 (8) | 0.0302 (9) | 0.0491 (9) | −0.0032 (7) | 0.0119 (7) | −0.0002 (7) |
C7 | 0.0377 (8) | 0.0290 (9) | 0.0531 (10) | −0.0011 (7) | 0.0128 (7) | −0.0052 (7) |
C8 | 0.0392 (8) | 0.0221 (8) | 0.0597 (10) | −0.0015 (7) | 0.0171 (7) | −0.0013 (7) |
C2 | 0.0575 (11) | 0.0298 (10) | 0.1001 (16) | 0.0062 (9) | 0.0408 (11) | 0.0098 (10) |
C10 | 0.0476 (10) | 0.0321 (10) | 0.0562 (11) | −0.0026 (8) | 0.0195 (8) | 0.0039 (8) |
C6 | 0.0599 (13) | 0.0455 (13) | 0.0992 (18) | −0.0064 (11) | 0.0386 (12) | −0.0288 (12) |
C3 | 0.0588 (13) | 0.0460 (15) | 0.151 (3) | −0.0153 (11) | 0.0519 (15) | −0.0309 (16) |
C5 | 0.0581 (13) | 0.0446 (13) | 0.1004 (18) | 0.0148 (11) | 0.0380 (12) | 0.0041 (12) |
S1—C9 | 1.7490 (17) | C7—C8 | 1.459 (2) |
S1—C10 | 1.803 (2) | C8—H8 | 0.87 (3) |
O1—C7 | 1.250 (2) | C2—H2A | 0.9700 |
O3—C11 | 1.214 (2) | C2—H2B | 0.9700 |
O2—C3 | 1.422 (3) | C2—C3 | 1.490 (3) |
O2—C5 | 1.408 (3) | C10—H10A | 0.99 (3) |
N2—C9 | 1.381 (2) | C10—H10B | 0.91 (3) |
N2—C11 | 1.363 (2) | C6—H6A | 0.9700 |
N2—H2 | 0.79 (3) | C6—H6B | 0.9700 |
N1—C7 | 1.353 (2) | C6—C5 | 1.472 (3) |
N1—C2 | 1.454 (3) | C3—H3A | 0.9700 |
N1—C6 | 1.462 (3) | C3—H3B | 0.9700 |
C9—C8 | 1.352 (2) | C5—H5A | 0.9700 |
C11—C10 | 1.503 (3) | C5—H5B | 0.9700 |
C9—S1—C10 | 92.02 (8) | C3—C2—H2B | 109.6 |
C5—O2—C3 | 110.09 (19) | S1—C10—H10A | 109.8 (18) |
C9—N2—H2 | 127 (2) | S1—C10—H10B | 117 (2) |
C11—N2—C9 | 118.05 (16) | C11—C10—S1 | 108.05 (13) |
C11—N2—H2 | 115 (2) | C11—C10—H10A | 114.0 (17) |
C7—N1—C2 | 126.90 (17) | C11—C10—H10B | 104 (2) |
C7—N1—C6 | 120.57 (17) | H10A—C10—H10B | 105 (3) |
C2—N1—C6 | 112.42 (17) | N1—C6—H6A | 109.6 |
N2—C9—S1 | 110.91 (12) | N1—C6—H6B | 109.6 |
C8—C9—S1 | 125.85 (14) | N1—C6—C5 | 110.34 (19) |
C8—C9—N2 | 123.23 (16) | H6A—C6—H6B | 108.1 |
O3—C11—N2 | 124.68 (18) | C5—C6—H6A | 109.6 |
O3—C11—C10 | 124.40 (16) | C5—C6—H6B | 109.6 |
N2—C11—C10 | 110.91 (16) | O2—C3—C2 | 112.8 (2) |
O1—C7—N1 | 120.81 (17) | O2—C3—H3A | 109.0 |
O1—C7—C8 | 120.27 (17) | O2—C3—H3B | 109.0 |
N1—C7—C8 | 118.92 (17) | C2—C3—H3A | 109.0 |
C9—C8—C7 | 120.57 (17) | C2—C3—H3B | 109.0 |
C9—C8—H8 | 119.9 (15) | H3A—C3—H3B | 107.8 |
C7—C8—H8 | 119.5 (16) | O2—C5—C6 | 111.7 (2) |
N1—C2—H2A | 109.6 | O2—C5—H5A | 109.3 |
N1—C2—H2B | 109.6 | O2—C5—H5B | 109.3 |
N1—C2—C3 | 110.2 (2) | C6—C5—H5A | 109.3 |
H2A—C2—H2B | 108.1 | C6—C5—H5B | 109.3 |
C3—C2—H2A | 109.6 | H5A—C5—H5B | 107.9 |
S1—C9—C8—C7 | 1.1 (3) | C7—N1—C2—C3 | 133.5 (2) |
O1—C7—C8—C9 | 8.3 (3) | C7—N1—C6—C5 | −130.8 (2) |
O3—C11—C10—S1 | 179.35 (16) | C2—N1—C7—O1 | −179.8 (2) |
N2—C9—C8—C7 | −179.01 (15) | C2—N1—C7—C8 | −0.6 (3) |
N2—C11—C10—S1 | −1.38 (19) | C2—N1—C6—C5 | 52.9 (3) |
N1—C7—C8—C9 | −170.79 (18) | C10—S1—C9—N2 | −2.10 (14) |
N1—C2—C3—O2 | 53.1 (3) | C10—S1—C9—C8 | 177.80 (17) |
N1—C6—C5—O2 | −57.3 (3) | C6—N1—C7—O1 | 4.4 (3) |
C9—S1—C10—C11 | 1.95 (14) | C6—N1—C7—C8 | −176.4 (2) |
C9—N2—C11—O3 | 179.09 (17) | C6—N1—C2—C3 | −50.5 (3) |
C9—N2—C11—C10 | −0.2 (2) | C3—O2—C5—C6 | 59.6 (3) |
C11—N2—C9—S1 | 1.7 (2) | C5—O2—C3—C2 | −57.7 (3) |
C11—N2—C9—C8 | −178.18 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O1i | 0.79 (3) | 2.11 (3) | 2.891 (2) | 167 (2) |
C2—H2A···S1i | 0.97 | 2.86 | 3.627 (2) | 137 |
C5—H5B···O3ii | 0.97 | 2.55 | 3.503 (3) | 167 |
C6—H6B···O3iii | 0.97 | 2.41 | 3.179 (3) | 136 |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x+1, −y+1/2, z−1/2; (iii) −x+1, y−1/2, −z+3/2. |
C12H12N2O3S | F(000) = 552 |
Mr = 264.30 | Dx = 1.474 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
Hall symbol: -P 2ybc | Cell parameters from 3173 reflections |
a = 11.628 (11) Å | θ = 3.8–65.3° |
b = 9.057 (6) Å | µ = 2.46 mm−1 |
c = 11.525 (12) Å | T = 295 K |
β = 101.13 (8)° | Prism, colourless |
V = 1190.8 (18) Å3 | 0.25 × 0.20 × 0.15 mm |
Z = 4 |
Oxford Diffraction Xcalibur 3 diffractometer | 2040 independent reflections |
Radiation source: fine-focus sealed tube | 1398 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.053 |
ω scans | θmax = 66.2°, θmin = 3.9° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006) | h = −12→13 |
Tmin = 0.742, Tmax = 1.000 | k = −9→10 |
8436 measured reflections | l = −13→13 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.105 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.060P)2] where P = (Fo2 + 2Fc2)/3 |
2040 reflections | (Δ/σ)max < 0.001 |
172 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.33 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. |
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 > 2sigma(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 | 0.12936 (5) | 0.11898 (8) | −0.00103 (5) | 0.0502 (2) | |
N1 | −0.17601 (18) | 0.4274 (3) | −0.04195 (17) | 0.0492 (5) | |
O1 | −0.46385 (19) | 0.6658 (2) | −0.43527 (18) | 0.0749 (6) | |
C1 | −0.2477 (2) | 0.4870 (3) | −0.1432 (2) | 0.0455 (6) | |
O2 | −0.04377 (14) | 0.2965 (2) | −0.12198 (14) | 0.0547 (5) | |
N2 | 0.10328 (18) | 0.1413 (3) | 0.21526 (18) | 0.0512 (6) | |
C2 | −0.3184 (2) | 0.6044 (3) | −0.1284 (2) | 0.0509 (6) | |
H2A | −0.3151 | 0.6431 | −0.0531 | 0.061* | |
O3 | 0.24270 (17) | −0.0064 (2) | 0.31929 (16) | 0.0660 (6) | |
C3 | −0.3939 (2) | 0.6656 (3) | −0.2224 (2) | 0.0575 (7) | |
H3A | −0.4420 | 0.7441 | −0.2108 | 0.069* | |
C4 | −0.3975 (2) | 0.6099 (3) | −0.3341 (2) | 0.0530 (6) | |
C5 | −0.3311 (2) | 0.4883 (3) | −0.3482 (2) | 0.0552 (7) | |
H5A | −0.3376 | 0.4468 | −0.4230 | 0.066* | |
C6 | −0.2555 (2) | 0.4267 (3) | −0.2548 (2) | 0.0510 (6) | |
H6A | −0.2101 | 0.3455 | −0.2663 | 0.061* | |
C7 | −0.0826 (2) | 0.3377 (3) | −0.0346 (2) | 0.0450 (6) | |
C8 | −0.0324 (2) | 0.2893 (3) | 0.0828 (2) | 0.0476 (6) | |
H8A | −0.0631 | 0.3248 | 0.1462 | 0.057* | |
C9 | 0.0570 (2) | 0.1951 (3) | 0.10347 (19) | 0.0443 (6) | |
C10 | 0.2276 (2) | 0.0170 (3) | 0.1101 (2) | 0.0528 (7) | |
H10A | 0.2212 | −0.0879 | 0.0930 | 0.063* | |
H10B | 0.3079 | 0.0473 | 0.1117 | 0.063* | |
C11 | 0.1943 (2) | 0.0481 (3) | 0.2273 (2) | 0.0512 (6) | |
C12 | −0.5271 (3) | 0.7961 (4) | −0.4254 (3) | 0.0815 (10) | |
H12A | −0.5700 | 0.8240 | −0.5019 | 0.122* | |
H12B | −0.4736 | 0.8737 | −0.3945 | 0.122* | |
H12C | −0.5807 | 0.7796 | −0.3730 | 0.122* | |
H1 | −0.198 (2) | 0.461 (3) | 0.029 (2) | 0.058 (7)* | |
H2 | 0.068 (3) | 0.163 (3) | 0.279 (2) | 0.067 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0518 (3) | 0.0662 (4) | 0.0356 (3) | −0.0033 (3) | 0.0159 (2) | −0.0037 (3) |
N1 | 0.0515 (11) | 0.0638 (14) | 0.0335 (11) | 0.0009 (10) | 0.0108 (9) | −0.0024 (10) |
O1 | 0.0742 (13) | 0.0805 (15) | 0.0637 (13) | 0.0219 (11) | −0.0025 (10) | 0.0061 (11) |
C1 | 0.0425 (12) | 0.0557 (15) | 0.0392 (13) | −0.0076 (11) | 0.0106 (10) | −0.0008 (11) |
O2 | 0.0519 (9) | 0.0796 (13) | 0.0353 (9) | 0.0040 (9) | 0.0151 (8) | 0.0008 (9) |
N2 | 0.0537 (12) | 0.0693 (15) | 0.0338 (11) | 0.0037 (11) | 0.0167 (9) | 0.0020 (10) |
C2 | 0.0518 (13) | 0.0555 (16) | 0.0470 (14) | −0.0058 (13) | 0.0136 (11) | −0.0108 (12) |
O3 | 0.0672 (12) | 0.0876 (15) | 0.0454 (12) | 0.0110 (10) | 0.0165 (9) | 0.0173 (10) |
C3 | 0.0524 (14) | 0.0550 (16) | 0.0645 (19) | 0.0025 (12) | 0.0097 (13) | −0.0084 (13) |
C4 | 0.0478 (13) | 0.0605 (16) | 0.0496 (15) | −0.0001 (13) | 0.0068 (11) | 0.0057 (13) |
C5 | 0.0561 (14) | 0.0723 (19) | 0.0381 (14) | 0.0075 (14) | 0.0113 (11) | −0.0013 (12) |
C6 | 0.0526 (13) | 0.0635 (17) | 0.0384 (13) | 0.0071 (13) | 0.0126 (11) | −0.0016 (12) |
C7 | 0.0431 (12) | 0.0559 (15) | 0.0384 (14) | −0.0087 (11) | 0.0138 (10) | −0.0031 (11) |
C8 | 0.0485 (13) | 0.0624 (17) | 0.0342 (13) | −0.0058 (12) | 0.0141 (10) | −0.0036 (11) |
C9 | 0.0471 (12) | 0.0549 (16) | 0.0328 (13) | −0.0093 (12) | 0.0126 (10) | 0.0006 (11) |
C10 | 0.0570 (14) | 0.0615 (17) | 0.0430 (15) | −0.0022 (13) | 0.0179 (11) | −0.0034 (12) |
C11 | 0.0521 (13) | 0.0652 (17) | 0.0383 (14) | −0.0058 (13) | 0.0138 (11) | 0.0053 (13) |
C12 | 0.0685 (19) | 0.079 (2) | 0.094 (3) | 0.0220 (18) | 0.0093 (17) | 0.0164 (19) |
S1—C9 | 1.739 (3) | C3—C4 | 1.375 (4) |
S1—C10 | 1.798 (3) | C3—H3A | 0.9300 |
N1—C7 | 1.346 (3) | C4—C5 | 1.372 (4) |
N1—C1 | 1.405 (3) | C5—C6 | 1.370 (4) |
N1—H1 | 0.96 (3) | C5—H5A | 0.9300 |
O1—C4 | 1.365 (3) | C6—H6A | 0.9300 |
O1—C12 | 1.407 (4) | C7—C8 | 1.435 (4) |
C1—C2 | 1.375 (4) | C8—C9 | 1.330 (4) |
C1—C6 | 1.384 (3) | C8—H8A | 0.9300 |
O2—C7 | 1.238 (3) | C10—C11 | 1.501 (4) |
N2—C11 | 1.339 (4) | C10—H10A | 0.9700 |
N2—C9 | 1.385 (3) | C10—H10B | 0.9700 |
N2—H2 | 0.92 (3) | C12—H12A | 0.9600 |
C2—C3 | 1.373 (4) | C12—H12B | 0.9600 |
C2—H2A | 0.9300 | C12—H12C | 0.9600 |
O3—C11 | 1.206 (3) | ||
C9—S1—C10 | 92.05 (13) | C1—C6—H6A | 120.4 |
C7—N1—C1 | 128.8 (2) | O2—C7—N1 | 123.1 (2) |
C7—N1—H1 | 119.0 (16) | O2—C7—C8 | 122.0 (2) |
C1—N1—H1 | 112.1 (16) | N1—C7—C8 | 114.9 (2) |
C4—O1—C12 | 117.4 (2) | C9—C8—C7 | 121.7 (2) |
C2—C1—C6 | 119.1 (2) | C9—C8—H8A | 119.1 |
C2—C1—N1 | 117.9 (2) | C7—C8—H8A | 119.1 |
C6—C1—N1 | 122.8 (2) | C8—C9—N2 | 122.8 (2) |
C11—N2—C9 | 118.4 (2) | C8—C9—S1 | 126.60 (19) |
C11—N2—H2 | 121.0 (17) | N2—C9—S1 | 110.58 (19) |
C9—N2—H2 | 120.5 (18) | C11—C10—S1 | 107.8 (2) |
C3—C2—C1 | 121.4 (2) | C11—C10—H10A | 110.1 |
C3—C2—H2A | 119.3 | S1—C10—H10A | 110.1 |
C1—C2—H2A | 119.3 | C11—C10—H10B | 110.1 |
C2—C3—C4 | 119.3 (3) | S1—C10—H10B | 110.1 |
C2—C3—H3A | 120.3 | H10A—C10—H10B | 108.5 |
C4—C3—H3A | 120.3 | O3—C11—N2 | 125.1 (2) |
O1—C4—C5 | 115.7 (2) | O3—C11—C10 | 123.8 (3) |
O1—C4—C3 | 125.0 (3) | N2—C11—C10 | 111.1 (2) |
C5—C4—C3 | 119.3 (2) | O1—C12—H12A | 109.5 |
C6—C5—C4 | 121.6 (2) | O1—C12—H12B | 109.5 |
C6—C5—H5A | 119.2 | H12A—C12—H12B | 109.5 |
C4—C5—H5A | 119.2 | O1—C12—H12C | 109.5 |
C5—C6—C1 | 119.1 (3) | H12A—C12—H12C | 109.5 |
C5—C6—H6A | 120.4 | H12B—C12—H12C | 109.5 |
C7—N1—C1—C2 | −163.6 (2) | C1—N1—C7—C8 | −176.5 (2) |
C7—N1—C1—C6 | 20.8 (4) | O2—C7—C8—C9 | −1.5 (4) |
C6—C1—C2—C3 | −2.0 (4) | N1—C7—C8—C9 | 176.9 (2) |
N1—C1—C2—C3 | −177.8 (2) | C7—C8—C9—N2 | −176.8 (2) |
C1—C2—C3—C4 | −1.0 (4) | C7—C8—C9—S1 | 1.6 (4) |
C12—O1—C4—C5 | −175.9 (3) | C11—N2—C9—C8 | −179.2 (2) |
C12—O1—C4—C3 | 4.5 (4) | C11—N2—C9—S1 | 2.2 (3) |
C2—C3—C4—O1 | −176.4 (2) | C10—S1—C9—C8 | 179.6 (2) |
C2—C3—C4—C5 | 4.1 (4) | C10—S1—C9—N2 | −1.85 (19) |
O1—C4—C5—C6 | 176.1 (2) | C9—S1—C10—C11 | 1.19 (19) |
C3—C4—C5—C6 | −4.2 (4) | C9—N2—C11—O3 | 179.9 (2) |
C4—C5—C6—C1 | 1.2 (4) | C9—N2—C11—C10 | −1.2 (3) |
C2—C1—C6—C5 | 1.9 (4) | S1—C10—C11—O3 | 178.6 (2) |
N1—C1—C6—C5 | 177.4 (2) | S1—C10—C11—N2 | −0.2 (3) |
C1—N1—C7—O2 | 1.9 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 0.95 (2) | 1.94 (2) | 2.883 (4) | 170 (2) |
N2—H2···O2ii | 0.93 (3) | 1.92 (3) | 2.828 (4) | 164 (3) |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) x, −y+1/2, z+1/2. |
Funding information
This work was supported by the Russian Science Foundation (grant No. 16–16-04022).
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