organic compounds
(Z)-5-(4-Bromophenyl)-3-{[(3,5-dichlorophenyl)amino]methylidene}furan-2(3H)-one
aInstitute of Biochemistry and Physiology of Plants and Microorganisms, Russian Academy of Sciences, 13 Prospekt Entuziastov, Saratov 410049, Russian Federation, and bInstitute of Chemistry, N. G. Chernyshevsky National Research Saratov State University, Ulitsa Astrakhanskaya, 83, Saratov 410012, Russian Federation
*Correspondence e-mail: grinev@ibppm.ru
The title compound, C17H10BrCl2NO2, crystallizes in the monoclinic C2/c with a large cell volume of 6207 (3) Å3. The of the title compound investigated at 120 K contains two crystallographically independent molecules (Z′ = 2). Each molecule demonstrates slight non-planarity in the solid state and a Z-configuration for the exocyclic C=C bond. The crystal packing reveals the presence of π-π stacking interactions between the substituted benzene rings [centroid–centroid distances of 3.836 (5) Å, shift distances in the range 1.272–1.843 Å].
Keywords: crystal structure; push–pull enamine; arylaminomethylene derivative; furan-2(3H)-one; halogen substituted; π–π stacking interactions.
CCDC reference: 2015222
Structure description
Push–pull H)-ones may be of interest for the creation of molecular switches (Osipov et al., 2017). Both crystallographically independent molecules of the title compound are close to planarity and may be aligned together with an r.m.s.d. of 0.297 Å without and 0.561 Å with inversion. Usually, pronounced non-planar molecules differ much more in their alignment with and without inversion. Actually, both molecules are slightly non-planar (Fig. 1) with the 4-bromophenyl substituent rotated about the mean plane of the furanone ring by approximately 2–5° [C18—C17—C6—O1 = 2.1 (12)° while the corresponding C18A—C17A—C6A—O1A torsion angle = 5.2 (13)°] . The C4=C7 as well as corresponding C4A=C7A bonds adopt a Z configuration. The benzene ring of the 3,5-dichlorophenyl substituent is also out of the plane of the molecule [the dihedral angles between the mean planes of the furanone and 3,5-dichlorophenyl rings are 33.6 (4) and 14.8 (4)°, respectively, for the two molecules], which is a consequence of the repulsion of hydrogen atoms H16/H16A of the aromatic substituent and H7/H7A of the enamine fragment with distances H7⋯H16 = 2.178 Å and H7A⋯H16A = 2.063 Å, which is less than the sum of the van der Waals radii (2.38 Å). This is in agreement with the observation that the interatomic distance is slightly larger in the more twisted molecule than in the more planar one.
based on furan-2(3In contrast to (Z)-3-[(3,5-dichloroanilino)methylidene]-5-(p-tolyl)furan-2(3H)-one (Grinev et al., 2018), which demonstrated only intramolecular hydrogen bond, in crystal of the title molecule there are not only intramolecular, but also intermolecular hydrogen bonds (Table 1, Fig. 2). They are relatively weak but result in dimer formation in the crystal packing. The H8⋯O3 distance in both molecules is significantly longer than the corresponding distance in the p-tolyl-substituted analogue [2.18 (2) Å]. This may be explained by the presence of the bulky electronegative bromine atom as a substituent on the benzene ring instead of a methyl group. The two molecules in the are oriented in a head-to-tail fashion, the bromine atom of one molecule becoming relatively close to the H atoms of CH fragments of both the aromatic and enamine moieties in the neighbouring second crystallographically independent molecule [H⋯Br interatomic distances are in the range 3.26—3.82 Å].
The interplanar distances between identically oriented molecules in the p-tolyl substituted analogue are larger than 7 Å, excluding non-covalent interactions such as π–π stacking. In contrast to this, in the crystal of the title molecule parallel-displaced π–π stacking interactions are present for both crystallographically independent molecules (Fig. 3). The intercentroid distances between the 3,5-dichlorophenyl as well as the 4-bromophenyl rings are 3.836 (5) Å for both molecules, with shift distances of 1.272 and 1.665 Å for the first molecule and 1.539 and 1.843 Å for the second molecule.
Synthesis and crystallization
The synthesis of the title compound was performed according to the method described by Osipov et al. (2017) and Grinev et al. (2018). Briefly, about 7 ml of benzene, 1.78 g of (12.02 mmol) triethyl orthoformate, 0.40 g (1.67 mmol) of 5-(4-bromophenyl)furan-2(3H)-one and 0.27 g (1.67 mmol) of 3,5-dichloroaniline were placed into a round-bottom flask equipped with a Liebig reflux condenser, and the reaction mixture was refluxed for 2 h. The precipitate of 3-[(3,5-dichloroanilino)methylidene]-5-(4-bromophenyl)furan-2(3H)-one was filtered off, washed with benzene and then with chloroform, dried, and recrystallized from DMF. Yield 0.51 g (75%), yellow crystals. A single crystal suitable for X-ray analysis was obtained by slow cooling of a of the title compound in benzene.
Refinement
Crystal data, data collection and structure . The relatively high Rint and R values as well as the low C—C bond precision are due to poor crystal quality because of probable or clustering.
details are summarized in Table 2
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Structural data
CCDC reference: 2015222
https://doi.org/10.1107/S2414314620009372/vm4045sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314620009372/vm4045Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314620009372/vm4045Isup3.cml
Data collection: APEX2 (Bruker, 2013); cell
SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: ShelXT (Sheldrick, 2015b); program(s) used to refine structure: SHELXL (Sheldrick, 2015a); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).C17H10BrCl2NO2 | F(000) = 3264 |
Mr = 411.07 | Dx = 1.760 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 55.051 (17) Å | Cell parameters from 1746 reflections |
b = 3.8355 (11) Å | θ = 2.8–30.7° |
c = 35.979 (12) Å | µ = 3.00 mm−1 |
β = 125.214 (6)° | T = 120 K |
V = 6207 (3) Å3 | Needle, metallic orangish yellow |
Z = 16 | 0.6 × 0.1 × 0.1 mm |
Bruker APEXII CCD diffractometer | 3647 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.136 |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | θmax = 26.0°, θmin = 0.9° |
Tmin = 0.170, Tmax = 0.337 | h = −66→65 |
17633 measured reflections | k = −4→4 |
6123 independent reflections | l = −41→44 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.092 | w = 1/[σ2(Fo2) + (0.0747P)2 + 74.2699P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.220 | (Δ/σ)max = 0.001 |
S = 1.06 | Δρmax = 1.17 e Å−3 |
6123 reflections | Δρmin = −1.30 e Å−3 |
359 parameters | Extinction correction: SHELXL2016/6 (Sheldrick 2016), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.00133 (13) |
Primary atom site location: dual |
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. The structure was solved by the internal phasing method and refined by the least-squares method in the anisotropic full-matrix approximation in accordance with F2hkl. Aromatic and amine H atoms refined with riding coordinates: C5(H5), C7(H7), C10(H10), C13(H13), C16(H16), C18(H18), C19(H19), C21(H21), C22(H22), N8A(H8A), C5A(H5A), C7A(H7A), C10A(H10A), C13A(H13A), C16A(H16A), C18A(H18A), C19A(H19A), C21A(H21A), C22A(H22A). Other H atoms were placed in calculated positions and refined geometrically using a riding model, with fixed thermal parameters Uiso(H) = 1.2Uiso(C). In addition, the following restraints and constraints were applied: Uanis(C6A) = Uanis(C6); Uanis(C16A) = Uanis(C10A) = Uanis(C16) = Uanis(C10); Uanis(C7A) = Uanis(C7); Uanis(C20) = Uanis(C20A); Uanis(C18) = Uanis(C22) = Uanis(C22A) = Uanis(C18A). |
x | y | z | Uiso*/Ueq | ||
Br23 | 0.48087 (2) | 1.1512 (3) | 0.68139 (4) | 0.0309 (3) | |
Cl1 | 0.14526 (6) | −0.0626 (7) | 0.33686 (10) | 0.0340 (7) | |
Cl15 | 0.20333 (6) | 0.2610 (8) | 0.26102 (10) | 0.0399 (7) | |
O1 | 0.32912 (15) | 0.9028 (18) | 0.5536 (2) | 0.0275 (17) | |
O3 | 0.27944 (15) | 0.865 (2) | 0.5197 (2) | 0.0338 (18) | |
N8 | 0.2499 (2) | 0.467 (2) | 0.4316 (3) | 0.029 (2) | |
H8 | 0.247 (2) | 0.48 (3) | 0.453 (4) | 0.035* | |
C2 | 0.3001 (2) | 0.796 (3) | 0.5180 (3) | 0.029 (3) | |
C4 | 0.3023 (2) | 0.614 (3) | 0.4849 (3) | 0.026 (2) | |
C5 | 0.3334 (2) | 0.613 (2) | 0.5017 (3) | 0.022 (2) | |
H5 | 0.341698 | 0.512110 | 0.487258 | 0.027* | |
C6 | 0.3483 (2) | 0.784 (2) | 0.5422 (3) | 0.0199 (15) | |
C7 | 0.2781 (2) | 0.477 (2) | 0.4441 (3) | 0.0236 (16) | |
H7 | 0.281853 | 0.381941 | 0.423527 | 0.028* | |
C9 | 0.2261 (2) | 0.345 (2) | 0.3887 (3) | 0.027 (2) | |
C10 | 0.2008 (2) | 0.216 (2) | 0.3845 (3) | 0.0223 (11) | |
H10 | 0.200137 | 0.208946 | 0.410275 | 0.027* | |
C11 | 0.1767 (2) | 0.097 (3) | 0.3425 (4) | 0.030 (3) | |
C13 | 0.1772 (2) | 0.103 (2) | 0.3038 (4) | 0.027 (2) | |
H13 | 0.160948 | 0.017098 | 0.275366 | 0.033* | |
C14 | 0.2023 (2) | 0.237 (3) | 0.3086 (3) | 0.023 (2) | |
C16 | 0.2270 (2) | 0.363 (2) | 0.3509 (3) | 0.0223 (11) | |
H16 | 0.243784 | 0.458461 | 0.353446 | 0.027* | |
C17 | 0.3802 (2) | 0.867 (2) | 0.5759 (3) | 0.0177 (14) | |
C18 | 0.3893 (2) | 1.041 (2) | 0.6163 (3) | 0.0216 (11) | |
H18 | 0.375138 | 1.102737 | 0.622215 | 0.026* | |
C19 | 0.4198 (2) | 1.123 (3) | 0.6482 (3) | 0.026 (2) | |
H19 | 0.426177 | 1.240856 | 0.675631 | 0.031* | |
C20 | 0.4401 (2) | 1.031 (3) | 0.6389 (4) | 0.0270 (17) | |
C21 | 0.4313 (2) | 0.856 (2) | 0.5991 (3) | 0.022 (2) | |
H21 | 0.445521 | 0.793918 | 0.593232 | 0.026* | |
C22 | 0.4007 (2) | 0.771 (2) | 0.5672 (3) | 0.0216 (11) | |
H22 | 0.394359 | 0.647951 | 0.540107 | 0.026* | |
Br1A | 0.28136 (2) | −0.0323 (3) | 0.32665 (4) | 0.0321 (3) | |
Cl2A | 0.62033 (6) | 1.0959 (7) | 0.68860 (9) | 0.0291 (6) | |
Cl3A | 0.55514 (6) | 0.6764 (7) | 0.74909 (9) | 0.0316 (6) | |
O1A | 0.42611 (14) | 0.5740 (16) | 0.4455 (2) | 0.0212 (15) | |
O3A | 0.47142 (15) | 0.8240 (17) | 0.4752 (2) | 0.0252 (16) | |
N8A | 0.51085 (17) | 0.717 (2) | 0.5780 (3) | 0.0213 (19) | |
H8A | 0.511802 | 0.804501 | 0.556191 | 0.026* | |
C2A | 0.4552 (2) | 0.657 (2) | 0.4813 (3) | 0.020 (2) | |
C4A | 0.4599 (2) | 0.516 (2) | 0.5227 (3) | 0.020 (2) | |
C5A | 0.4325 (2) | 0.348 (2) | 0.5088 (3) | 0.019 (2) | |
H5A | 0.428873 | 0.227865 | 0.528260 | 0.023* | |
C6A | 0.4130 (2) | 0.391 (2) | 0.4639 (3) | 0.0199 (15) | |
C7A | 0.4858 (2) | 0.543 (2) | 0.5660 (3) | 0.0236 (16) | |
H7A | 0.486133 | 0.428201 | 0.589717 | 0.028* | |
C9A | 0.5354 (2) | 0.766 (3) | 0.6235 (3) | 0.021 (2) | |
C10A | 0.5626 (2) | 0.887 (2) | 0.6326 (3) | 0.0223 (11) | |
H10A | 0.564462 | 0.929666 | 0.608312 | 0.027* | |
C11A | 0.5865 (2) | 0.944 (3) | 0.6769 (3) | 0.023 (2) | |
C13A | 0.5849 (2) | 0.882 (3) | 0.7136 (3) | 0.026 (2) | |
H13A | 0.601535 | 0.923528 | 0.743953 | 0.031* | |
C14A | 0.5582 (2) | 0.758 (2) | 0.7044 (3) | 0.023 (2) | |
C16A | 0.5334 (2) | 0.706 (2) | 0.6597 (3) | 0.0223 (11) | |
H16A | 0.515162 | 0.630053 | 0.654176 | 0.027* | |
C17A | 0.3814 (2) | 0.289 (2) | 0.4306 (3) | 0.0177 (14) | |
C18A | 0.3672 (2) | 0.348 (2) | 0.3842 (3) | 0.0216 (11) | |
H18A | 0.377945 | 0.448435 | 0.373662 | 0.026* | |
C19A | 0.3374 (2) | 0.260 (2) | 0.3532 (3) | 0.022 (2) | |
H19A | 0.327384 | 0.310506 | 0.321743 | 0.026* | |
C20A | 0.3224 (2) | 0.097 (3) | 0.3692 (4) | 0.0270 (17) | |
C21A | 0.3361 (2) | 0.038 (2) | 0.4148 (4) | 0.027 (2) | |
H21A | 0.325416 | −0.068515 | 0.425210 | 0.032* | |
C22A | 0.3657 (2) | 0.134 (2) | 0.4456 (3) | 0.0216 (11) | |
H22A | 0.375192 | 0.094617 | 0.477202 | 0.026* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br23 | 0.0239 (6) | 0.0206 (6) | 0.0413 (7) | −0.0040 (4) | 0.0149 (5) | −0.0004 (5) |
Cl1 | 0.0339 (15) | 0.0288 (15) | 0.0475 (17) | −0.0050 (12) | 0.0282 (14) | −0.0047 (12) |
Cl15 | 0.0389 (16) | 0.0507 (19) | 0.0385 (17) | 0.0045 (14) | 0.0273 (14) | 0.0024 (14) |
O1 | 0.025 (4) | 0.036 (4) | 0.030 (4) | −0.010 (3) | 0.021 (3) | −0.007 (3) |
O3 | 0.020 (4) | 0.047 (5) | 0.040 (5) | −0.004 (3) | 0.021 (4) | −0.005 (4) |
N8 | 0.030 (5) | 0.031 (5) | 0.027 (5) | −0.004 (4) | 0.017 (4) | 0.005 (4) |
C2 | 0.018 (5) | 0.041 (7) | 0.020 (5) | −0.014 (5) | 0.007 (4) | 0.007 (5) |
C4 | 0.029 (6) | 0.026 (6) | 0.022 (5) | −0.007 (5) | 0.014 (5) | 0.006 (4) |
C5 | 0.037 (6) | 0.013 (5) | 0.026 (6) | −0.004 (4) | 0.022 (5) | 0.001 (4) |
C6 | 0.023 (4) | 0.011 (3) | 0.033 (4) | −0.004 (3) | 0.021 (3) | −0.003 (3) |
C7 | 0.032 (4) | 0.009 (4) | 0.032 (4) | −0.004 (3) | 0.020 (3) | −0.004 (3) |
C9 | 0.033 (6) | 0.008 (5) | 0.028 (6) | 0.005 (4) | 0.010 (5) | 0.003 (4) |
C10 | 0.026 (3) | 0.013 (3) | 0.032 (3) | 0.002 (2) | 0.020 (2) | 0.001 (2) |
C11 | 0.035 (6) | 0.022 (6) | 0.037 (6) | 0.007 (5) | 0.022 (5) | −0.004 (5) |
C13 | 0.029 (6) | 0.017 (5) | 0.038 (6) | 0.010 (4) | 0.020 (5) | 0.005 (5) |
C14 | 0.022 (5) | 0.019 (5) | 0.027 (6) | 0.007 (4) | 0.014 (5) | 0.005 (4) |
C16 | 0.026 (3) | 0.013 (3) | 0.032 (3) | 0.002 (2) | 0.020 (2) | 0.001 (2) |
C17 | 0.023 (3) | 0.012 (3) | 0.028 (4) | −0.001 (3) | 0.021 (3) | −0.001 (3) |
C18 | 0.027 (3) | 0.017 (3) | 0.030 (3) | −0.001 (2) | 0.022 (2) | 0.000 (2) |
C19 | 0.023 (5) | 0.028 (6) | 0.030 (6) | −0.012 (4) | 0.018 (5) | −0.008 (5) |
C20 | 0.027 (4) | 0.018 (4) | 0.037 (4) | −0.003 (3) | 0.019 (3) | 0.004 (3) |
C21 | 0.021 (5) | 0.017 (5) | 0.030 (6) | −0.004 (4) | 0.017 (5) | −0.006 (4) |
C22 | 0.027 (3) | 0.017 (3) | 0.030 (3) | −0.001 (2) | 0.022 (2) | 0.000 (2) |
Br1A | 0.0217 (5) | 0.0293 (7) | 0.0428 (7) | −0.0055 (5) | 0.0171 (5) | −0.0041 (5) |
Cl2A | 0.0262 (13) | 0.0328 (15) | 0.0328 (14) | −0.0045 (11) | 0.0196 (12) | −0.0021 (12) |
Cl3A | 0.0424 (16) | 0.0316 (15) | 0.0262 (14) | −0.0033 (12) | 0.0228 (13) | 0.0014 (11) |
O1A | 0.020 (3) | 0.019 (4) | 0.024 (4) | −0.004 (3) | 0.013 (3) | −0.001 (3) |
O3A | 0.025 (4) | 0.024 (4) | 0.036 (4) | −0.011 (3) | 0.023 (3) | −0.004 (3) |
N8A | 0.028 (5) | 0.020 (5) | 0.021 (4) | −0.001 (4) | 0.017 (4) | 0.000 (3) |
C2A | 0.019 (5) | 0.015 (5) | 0.030 (6) | −0.003 (4) | 0.015 (4) | −0.009 (4) |
C4A | 0.034 (6) | 0.008 (5) | 0.031 (6) | 0.001 (4) | 0.025 (5) | 0.002 (4) |
C5A | 0.027 (5) | 0.020 (5) | 0.016 (5) | −0.003 (4) | 0.016 (4) | 0.000 (4) |
C6A | 0.023 (4) | 0.011 (3) | 0.033 (4) | −0.004 (3) | 0.021 (3) | −0.003 (3) |
C7A | 0.032 (4) | 0.009 (4) | 0.032 (4) | −0.004 (3) | 0.020 (3) | −0.004 (3) |
C9A | 0.018 (5) | 0.022 (6) | 0.025 (5) | −0.003 (4) | 0.013 (4) | 0.002 (4) |
C10A | 0.026 (3) | 0.013 (3) | 0.032 (3) | 0.002 (2) | 0.020 (2) | 0.001 (2) |
C11A | 0.022 (5) | 0.021 (6) | 0.029 (6) | 0.002 (4) | 0.016 (5) | −0.002 (4) |
C13A | 0.033 (6) | 0.023 (6) | 0.026 (6) | 0.009 (5) | 0.019 (5) | 0.006 (4) |
C14A | 0.034 (6) | 0.008 (5) | 0.031 (6) | 0.002 (4) | 0.021 (5) | 0.006 (4) |
C16A | 0.026 (3) | 0.013 (3) | 0.032 (3) | 0.002 (2) | 0.020 (2) | 0.001 (2) |
C17A | 0.023 (3) | 0.012 (3) | 0.028 (4) | −0.001 (3) | 0.021 (3) | −0.001 (3) |
C18A | 0.027 (3) | 0.017 (3) | 0.030 (3) | −0.001 (2) | 0.022 (2) | 0.000 (2) |
C19A | 0.019 (5) | 0.020 (5) | 0.024 (5) | −0.002 (4) | 0.011 (4) | 0.002 (4) |
C20A | 0.027 (4) | 0.018 (4) | 0.037 (4) | −0.003 (3) | 0.019 (3) | 0.004 (3) |
C21A | 0.032 (6) | 0.014 (5) | 0.046 (7) | 0.002 (4) | 0.029 (6) | 0.006 (5) |
C22A | 0.027 (3) | 0.017 (3) | 0.030 (3) | −0.001 (2) | 0.022 (2) | 0.000 (2) |
Br23—C20 | 1.907 (10) | Br1A—C20A | 1.926 (10) |
Cl1—C11 | 1.732 (11) | Cl2A—C11A | 1.756 (10) |
Cl15—C14 | 1.746 (10) | Cl3A—C14A | 1.740 (10) |
O1—C2 | 1.412 (11) | O1A—C2A | 1.395 (11) |
O1—C6 | 1.409 (11) | O1A—C6A | 1.416 (11) |
O3—C2 | 1.204 (12) | O3A—C2A | 1.220 (11) |
N8—H8 | 0.86 (10) | N8A—H8A | 0.8800 |
N8—C7 | 1.342 (13) | N8A—C7A | 1.361 (12) |
N8—C9 | 1.411 (13) | N8A—C9A | 1.412 (12) |
C2—C4 | 1.445 (15) | C2A—C4A | 1.457 (13) |
C4—C5 | 1.448 (14) | C4A—C5A | 1.440 (13) |
C4—C7 | 1.397 (14) | C4A—C7A | 1.382 (14) |
C5—H5 | 0.9500 | C5A—H5A | 0.9500 |
C5—C6 | 1.360 (13) | C5A—C6A | 1.339 (13) |
C6—C17 | 1.486 (13) | C6A—C17A | 1.487 (13) |
C7—H7 | 0.9500 | C7A—H7A | 0.9500 |
C9—C10 | 1.400 (14) | C9A—C10A | 1.417 (13) |
C9—C16 | 1.389 (14) | C9A—C16A | 1.388 (13) |
C10—H10 | 0.9500 | C10A—H10A | 0.9500 |
C10—C11 | 1.393 (14) | C10A—C11A | 1.378 (14) |
C11—C13 | 1.410 (15) | C11A—C13A | 1.392 (14) |
C13—H13 | 0.9500 | C13A—H13A | 0.9500 |
C13—C14 | 1.390 (14) | C13A—C14A | 1.390 (14) |
C14—C16 | 1.418 (14) | C14A—C16A | 1.400 (14) |
C16—H16 | 0.9500 | C16A—H16A | 0.9500 |
C17—C18 | 1.403 (13) | C17A—C18A | 1.392 (13) |
C17—C22 | 1.380 (12) | C17A—C22A | 1.391 (13) |
C18—H18 | 0.9500 | C18A—H18A | 0.9500 |
C18—C19 | 1.417 (13) | C18A—C19A | 1.394 (13) |
C19—H19 | 0.9500 | C19A—H19A | 0.9500 |
C19—C20 | 1.385 (14) | C19A—C20A | 1.393 (14) |
C20—C21 | 1.391 (14) | C20A—C21A | 1.375 (14) |
C21—H21 | 0.9500 | C21A—H21A | 0.9500 |
C21—C22 | 1.427 (13) | C21A—C22A | 1.392 (14) |
C22—H22 | 0.9500 | C22A—H22A | 0.9500 |
C6—O1—C2 | 106.7 (8) | C2A—O1A—C6A | 107.7 (7) |
C7—N8—H8 | 118 (8) | C7A—N8A—H8A | 118.4 |
C7—N8—C9 | 122.8 (9) | C7A—N8A—C9A | 123.3 (8) |
C9—N8—H8 | 117 (8) | C9A—N8A—H8A | 118.4 |
O1—C2—C4 | 107.4 (9) | O1A—C2A—C4A | 107.1 (8) |
O3—C2—O1 | 119.9 (10) | O3A—C2A—O1A | 121.4 (9) |
O3—C2—C4 | 132.6 (9) | O3A—C2A—C4A | 131.5 (9) |
C2—C4—C5 | 107.3 (9) | C5A—C4A—C2A | 106.1 (8) |
C7—C4—C2 | 124.4 (10) | C7A—C4A—C2A | 125.8 (9) |
C7—C4—C5 | 128.3 (10) | C7A—C4A—C5A | 128.1 (9) |
C4—C5—H5 | 126.8 | C4A—C5A—H5A | 125.8 |
C6—C5—C4 | 106.4 (9) | C6A—C5A—C4A | 108.3 (8) |
C6—C5—H5 | 126.8 | C6A—C5A—H5A | 125.8 |
O1—C6—C17 | 115.2 (8) | O1A—C6A—C17A | 115.4 (8) |
C5—C6—O1 | 112.2 (8) | C5A—C6A—O1A | 110.8 (8) |
C5—C6—C17 | 132.5 (9) | C5A—C6A—C17A | 133.8 (9) |
N8—C7—C4 | 125.5 (10) | N8A—C7A—C4A | 126.2 (9) |
N8—C7—H7 | 117.2 | N8A—C7A—H7A | 116.9 |
C4—C7—H7 | 117.2 | C4A—C7A—H7A | 116.9 |
C10—C9—N8 | 118.4 (9) | N8A—C9A—C10A | 119.3 (8) |
C16—C9—N8 | 121.2 (10) | C16A—C9A—N8A | 121.8 (9) |
C16—C9—C10 | 120.3 (9) | C16A—C9A—C10A | 118.9 (9) |
C9—C10—H10 | 120.0 | C9A—C10A—H10A | 120.2 |
C11—C10—C9 | 120.0 (10) | C11A—C10A—C9A | 119.7 (9) |
C11—C10—H10 | 120.0 | C11A—C10A—H10A | 120.2 |
C10—C11—Cl1 | 120.5 (8) | C10A—C11A—Cl2A | 120.0 (8) |
C10—C11—C13 | 121.0 (10) | C10A—C11A—C13A | 122.1 (10) |
C13—C11—Cl1 | 118.6 (8) | C13A—C11A—Cl2A | 117.9 (8) |
C11—C13—H13 | 121.0 | C11A—C13A—H13A | 121.0 |
C14—C13—C11 | 118.1 (10) | C14A—C13A—C11A | 117.9 (10) |
C14—C13—H13 | 121.0 | C14A—C13A—H13A | 121.0 |
C13—C14—Cl15 | 119.3 (8) | C13A—C14A—Cl3A | 119.7 (8) |
C13—C14—C16 | 121.7 (10) | C13A—C14A—C16A | 121.3 (9) |
C16—C14—Cl15 | 119.0 (8) | C16A—C14A—Cl3A | 119.0 (8) |
C9—C16—C14 | 118.9 (9) | C9A—C16A—C14A | 120.1 (9) |
C9—C16—H16 | 120.6 | C9A—C16A—H16A | 119.9 |
C14—C16—H16 | 120.6 | C14A—C16A—H16A | 119.9 |
C18—C17—C6 | 119.6 (8) | C18A—C17A—C6A | 120.7 (8) |
C22—C17—C6 | 119.6 (8) | C22A—C17A—C6A | 119.9 (9) |
C22—C17—C18 | 120.8 (9) | C22A—C17A—C18A | 119.3 (9) |
C17—C18—H18 | 120.2 | C17A—C18A—H18A | 119.7 |
C17—C18—C19 | 119.5 (9) | C17A—C18A—C19A | 120.5 (9) |
C19—C18—H18 | 120.2 | C19A—C18A—H18A | 119.7 |
C18—C19—H19 | 120.3 | C18A—C19A—H19A | 120.6 |
C20—C19—C18 | 119.3 (9) | C20A—C19A—C18A | 118.7 (9) |
C20—C19—H19 | 120.3 | C20A—C19A—H19A | 120.6 |
C19—C20—Br23 | 119.0 (8) | C19A—C20A—Br1A | 119.3 (8) |
C19—C20—C21 | 121.5 (9) | C21A—C20A—Br1A | 119.2 (8) |
C21—C20—Br23 | 119.4 (8) | C21A—C20A—C19A | 121.5 (10) |
C20—C21—H21 | 120.5 | C20A—C21A—H21A | 120.4 |
C20—C21—C22 | 119.0 (9) | C20A—C21A—C22A | 119.3 (9) |
C22—C21—H21 | 120.5 | C22A—C21A—H21A | 120.4 |
C17—C22—C21 | 119.8 (9) | C17A—C22A—C21A | 120.6 (9) |
C17—C22—H22 | 120.1 | C17A—C22A—H22A | 119.7 |
C21—C22—H22 | 120.1 | C21A—C22A—H22A | 119.7 |
D—H···A | D—H | H···A | D···A | D—H···A |
N8—H8···O3 | 0.87 (13) | 2.49 (11) | 3.013 (11) | 119 (10) |
N8—H8···O3i | 0.87 (13) | 2.26 (13) | 3.059 (15) | 153 (11) |
N8A—H8A···O3A | 0.88 | 2.44 | 3.050 (11) | 126 |
N8A—H8A···O3Aii | 0.88 | 2.32 | 3.142 (12) | 156 |
Symmetry codes: (i) −x+1/2, −y+3/2, −z+1; (ii) −x+1, −y+2, −z+1. |
Funding information
Funding for this research was provided by: Russian Foundation for Basic Research (grant No. 19-33-60038 to O. A. Mayorova).
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