research communications
E,1′E)-[4,4′-(9H-fluorene-9,9-diyl)bis(4,1-phenylene)]bis(azanylylidene)bis(methanylylidene)}bis(naphthalen-2-ol) dichlorobenzene monosolvate
of 1,1′-{(1aCollege of Natural and Computational Sciences, University of Gondar, 196 Gondar, Ethiopia, bN. N. Semenov Federal Research Center for Chemical Physics, Russian Academy of Sciences, Ul. Kosygina 4, Moscow, Russian Federation, cPeoples Friendship University of Russia, 6 Miklukho-Maklaya Street, Moscow, 117198, Russian Federation, dFaculty of Chemistry, VNU University of Science, 334 Nguyen Trai, Thanh Xuan, Hanoi, Vietnam, and eKurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninsky Prosp. 31, Moscow, Russian Federation
*Correspondence e-mail: alexander.tskhovrebov@gmail.com
The bis(anil) molecule of the title compound, C47H32N2O2·C6H4Cl2, contains two anil fragments in the enol–enol form, exhibiting intramolecular O—H⋯N hydrogen bonds. The two hydroxynaphthalene ring systems are approximately parallel to each other with a dihedral angle of 4.67 (8)° between them, and each ring system makes a large dihedral angle [55.11 (11) and 48.50 (10)°] with the adjacent benzene ring. In the crystal, the bis(anil) molecules form an inversion dimer by a pair of weak C—H⋯O interactions. The dimers arrange in a one-dimensional column along the b axis via another C—H⋯O interaction and a π–π stacking interaction between the hydroxynaphthalene ring system with a centroid–centroid distance of 3.6562 (16) Å. The solvent 1,2-dichlorobenzene molecules are located between the dimers and bind neighbouring columns by weak C—H⋯Cl interactions. Theoretical prediction of potential biological activities was performed, which suggested that the title anil compound can exhibit histone deacetylase SIRT2, histone deacetylase class III and histone deacetylase SIRT1 activities, and will act as inhibitor to aspulvinone dimethylallyltransferase, dehydro-L-gulonate decarboxylase and glutathione thiolesterase.
Keywords: azomethines; imines; hydrogen bonding; weak interactions; excited-state intramolecular proton transfer; crystal structure.
CCDC reference: 2019265
1. Chemical context
). In addition, they are an important class of ligands, which are widely used in inorganic and coordination chemistry (Devi et al., 2019). Non-coordinating undergo excited-state intramolecular proton transfer (ESIPT), which make them attractive objects for photophysical investigations (Minkin et al., 2011; Cohen & Schmidt, 1962). Their colours and proton-transfer equilibrium is greatly dependent on the substituents in the core (Sliwa et al., 2009, 2010). Here we describe a of the title compound, which was synthesized by the condensation between 4,4′-(9H-fluorene-9,9-diyl)dianiline and two equivalents of 2-hydroxy-1-naphthaldehyde. According to the PASS program – computer prediction of biological activities (Filimonov et al., 2014), the title compound will exhibit histone deacetylase SIRT2, histone deacetylase class III and histone deacetylase SIRT1 (91, 86 and 73%, respectively), and will act inhibitor of enzymes, such as aspulvinone dimethylallyltransferase (81% probability), dehydro-L-gulonate decarboxylase (75%) and glutathione thiolesterase (71%).
formed by the condensation of salicylaldehydes with are also known as They often exhibit potent antibacterial, antiproliferative and antitoxic properties (Williams, 19722. Structural commentary
In the title bis(anil) molecule, two hydroxynaphthalene ring systems are approximately parallel to each other with a dihedral angle of 4.67 (8)° between them (Fig. 1). The 9H-fluorene ring system (C1–C13) forms large dihedral angles of 78.80 (10) and 61.41 (9)°, respectively, with the benzene C14–C19 and C31–C36 rings. Each hydroxynaphthalene ring system also forms a large dihedral angle with the adjacent benzene ring [55.11 (11)° between the C21–C30 ring system and the C14–C19 ring, and 48.50 (10)° between the C38–C47 ring system and the C31–C36 ring]. Both fragments of the hydroxynaphthalene are in the enol form, forming intramolecular O—H⋯N hydrogen bonds (Table 1).
3. Supramolecular features
In the crystal, the bis(anil) molecules form an inversion dimer via a pair of weak C—H⋯O interactions (C3—H3⋯O1i; symmetry code given in Table 1). The dimers form a 1D column along the b axis through a C—H⋯O (C35—H35⋯O1ii; Table 1) and a π–π stacking interaction between the hydroxyl naphthalene ring systems with a centroid-centroid distance of 3.6562 (16) Å (Cg1⋯Cg2ii; Cg1 and Cg2 are the centroids of C21–C30 and C38–C47 ring systems, respectively). Dichlorobenzene molecules are located between the dimers and bind the neighboring columns by weak C—H⋯Cl interactions (Table 1 and Fig. 2).
4. Database survey
A search of the Cambridge Structural Database (CSD version 5.41, update of March, 2020; Groom et al., 2016) revealed the existence of several structurally similar bis-hydroxyimines derivatives. All of them were prepared via the condensation of the corresponding diamine and an appropriate hydroxyaldehyde (Elmali et al., 1995; Blagus & Kaitner, 2011; Popović et al., 2001; Meng et al., 2008; Wang et al., 2016; Han et al., 2015). Interestingly, although keto–enol tautamerization is a well-established phenomenon for such systems, the majority of known bis-hydroxyimines exist in enol-enol forms, except the one reported by Popović et al. (2001).
5. Synthesis and crystallization
The compound was obtained by the condensation between 2-hydroxy-1-naphthaldehyde and 4,4′-(9H-fluorene-9,9-diyl)dianiline according to the literature (Elhusseiny et al., 2015; Kundu et al., 2015). Single crystals suitable for the X-ray analysis were obtained by the slow evaporation of a saturated 1,2-dichlorobenzene solution.
6. Refinement
Crystal data, details of data collection, and results of structure . All C-bound H atoms were placed in calculated positions (C—H = 0.95 Å) and refined using a riding model [Uiso(H) = 1.2Ueq(C)], while the H atoms of the OH groups were localized in a difference-Fourier map and refined with Uiso(H) = 1.5Ueq(O).
are summarized in Table 2
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Supporting information
CCDC reference: 2019265
https://doi.org/10.1107/S2056989020012104/is5554sup1.cif
contains datablocks general, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989020012104/is5554Isup2.hkl
Data collection: APEX3 (Bruker, 2018); cell
SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).C47H32N2O2·C6H4Cl2 | F(000) = 1672 |
Mr = 803.74 | Dx = 1.378 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.3070 (6) Å | Cell parameters from 6276 reflections |
b = 9.1782 (4) Å | θ = 2.6–29.6° |
c = 32.2298 (16) Å | µ = 0.22 mm−1 |
β = 100.251 (2)° | T = 100 K |
V = 3873.5 (3) Å3 | Plate, yellow |
Z = 4 | 0.8 × 0.4 × 0.1 mm |
Bruker APEXII CCD diffractometer | 5542 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.036 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | θmax = 26.0°, θmin = 1.8° |
Tmin = 0.596, Tmax = 0.746 | h = −16→16 |
18958 measured reflections | k = −10→11 |
7377 independent reflections | l = −33→39 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.053 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.140 | w = 1/[σ2(Fo2) + (0.0606P)2 + 3.6798P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
7377 reflections | Δρmax = 0.33 e Å−3 |
538 parameters | Δρmin = −0.41 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 | ||
Cl1 | 0.86399 (5) | 0.50325 (8) | 0.48868 (2) | 0.03159 (18) | |
Cl2 | 0.67342 (7) | 0.49018 (11) | 0.53468 (2) | 0.0506 (2) | |
C48 | 0.7535 (2) | 0.4140 (3) | 0.46574 (8) | 0.0240 (6) | |
C49 | 0.6694 (2) | 0.4093 (3) | 0.48571 (8) | 0.0293 (6) | |
C50 | 0.5823 (2) | 0.3367 (3) | 0.46676 (10) | 0.0363 (7) | |
H50 | 0.524224 | 0.334047 | 0.480129 | 0.044* | |
C51 | 0.5794 (2) | 0.2680 (3) | 0.42838 (10) | 0.0374 (7) | |
H51 | 0.519534 | 0.217721 | 0.415533 | 0.045* | |
C52 | 0.6634 (2) | 0.2723 (3) | 0.40872 (10) | 0.0341 (7) | |
H52 | 0.661665 | 0.223847 | 0.382545 | 0.041* | |
C53 | 0.7503 (2) | 0.3472 (3) | 0.42716 (8) | 0.0275 (6) | |
H53 | 0.807552 | 0.352531 | 0.413313 | 0.033* | |
O1 | 0.67650 (15) | 0.8293 (2) | 0.59900 (6) | 0.0254 (4) | |
H1 | 0.655 (2) | 0.836 (3) | 0.5719 (10) | 0.038* | |
O2 | 0.00869 (17) | 0.3629 (2) | 0.27222 (6) | 0.0346 (5) | |
H2 | 0.071 (3) | 0.422 (4) | 0.2835 (11) | 0.052* | |
N1 | 0.67572 (17) | 0.9057 (2) | 0.52365 (6) | 0.0218 (5) | |
N2 | 0.15609 (16) | 0.4833 (2) | 0.32226 (7) | 0.0224 (5) | |
C1 | 0.54205 (19) | 0.7866 (3) | 0.34681 (7) | 0.0185 (5) | |
C2 | 0.53815 (19) | 0.9371 (3) | 0.32573 (7) | 0.0178 (5) | |
C3 | 0.4827 (2) | 1.0591 (3) | 0.33307 (8) | 0.0217 (6) | |
H3 | 0.439149 | 1.056724 | 0.353428 | 0.026* | |
C4 | 0.4920 (2) | 1.1856 (3) | 0.31005 (8) | 0.0255 (6) | |
H4 | 0.454262 | 1.270090 | 0.314727 | 0.031* | |
C5 | 0.5559 (2) | 1.1893 (3) | 0.28034 (8) | 0.0285 (6) | |
H5 | 0.561040 | 1.275926 | 0.264729 | 0.034* | |
C6 | 0.6123 (2) | 1.0679 (3) | 0.27327 (8) | 0.0261 (6) | |
H6 | 0.656020 | 1.070707 | 0.252987 | 0.031* | |
C7 | 0.60383 (19) | 0.9421 (3) | 0.29627 (7) | 0.0208 (5) | |
C8 | 0.65444 (19) | 0.8007 (3) | 0.29556 (8) | 0.0213 (5) | |
C9 | 0.7264 (2) | 0.7520 (3) | 0.27193 (8) | 0.0274 (6) | |
H9 | 0.750623 | 0.815367 | 0.252576 | 0.033* | |
C10 | 0.7617 (2) | 0.6106 (3) | 0.27713 (9) | 0.0316 (7) | |
H10 | 0.810846 | 0.576477 | 0.261388 | 0.038* | |
C11 | 0.7257 (2) | 0.5180 (3) | 0.30522 (9) | 0.0300 (6) | |
H11 | 0.750040 | 0.420553 | 0.308222 | 0.036* | |
C12 | 0.6548 (2) | 0.5654 (3) | 0.32899 (8) | 0.0245 (6) | |
H12 | 0.630758 | 0.501280 | 0.348205 | 0.029* | |
C13 | 0.61944 (19) | 0.7073 (3) | 0.32437 (7) | 0.0202 (5) | |
C14 | 0.58069 (19) | 0.8082 (3) | 0.39440 (7) | 0.0187 (5) | |
C15 | 0.5104 (2) | 0.8411 (3) | 0.42059 (8) | 0.0219 (6) | |
H15 | 0.439472 | 0.842256 | 0.409218 | 0.026* | |
C16 | 0.5432 (2) | 0.8722 (3) | 0.46297 (8) | 0.0215 (5) | |
H16 | 0.494462 | 0.891713 | 0.480497 | 0.026* | |
C17 | 0.64629 (19) | 0.8750 (3) | 0.47993 (8) | 0.0194 (5) | |
C18 | 0.71678 (19) | 0.8396 (3) | 0.45441 (8) | 0.0206 (5) | |
H18 | 0.787676 | 0.838484 | 0.465863 | 0.025* | |
C19 | 0.6834 (2) | 0.8059 (3) | 0.41211 (8) | 0.0212 (5) | |
H19 | 0.732035 | 0.780775 | 0.395037 | 0.025* | |
C20 | 0.75022 (19) | 0.9948 (3) | 0.53695 (8) | 0.0206 (5) | |
H20 | 0.780899 | 1.046811 | 0.516987 | 0.025* | |
C21 | 0.78777 (19) | 1.0168 (3) | 0.58159 (8) | 0.0199 (5) | |
C22 | 0.75129 (19) | 0.9278 (3) | 0.61090 (8) | 0.0201 (5) | |
C23 | 0.7938 (2) | 0.9344 (3) | 0.65415 (8) | 0.0233 (6) | |
H23 | 0.767240 | 0.874321 | 0.673656 | 0.028* | |
C24 | 0.8724 (2) | 1.0262 (3) | 0.66798 (8) | 0.0240 (6) | |
H24 | 0.901129 | 1.027626 | 0.697156 | 0.029* | |
C25 | 0.9131 (2) | 1.1202 (3) | 0.64022 (8) | 0.0227 (6) | |
C26 | 0.9951 (2) | 1.2152 (3) | 0.65491 (9) | 0.0273 (6) | |
H26 | 1.024204 | 1.215786 | 0.684048 | 0.033* | |
C27 | 1.0332 (2) | 1.3061 (3) | 0.62817 (9) | 0.0300 (6) | |
H27 | 1.089811 | 1.367247 | 0.638394 | 0.036* | |
C28 | 0.9882 (2) | 1.3087 (3) | 0.58537 (9) | 0.0311 (7) | |
H28 | 1.013243 | 1.374462 | 0.566853 | 0.037* | |
C29 | 0.9088 (2) | 1.2179 (3) | 0.56990 (8) | 0.0254 (6) | |
H29 | 0.879911 | 1.221614 | 0.540761 | 0.031* | |
C30 | 0.86878 (19) | 1.1184 (3) | 0.59640 (8) | 0.0203 (5) | |
C31 | 0.43890 (19) | 0.7081 (3) | 0.33971 (7) | 0.0179 (5) | |
C32 | 0.35105 (19) | 0.7645 (3) | 0.31484 (7) | 0.0190 (5) | |
H32 | 0.354567 | 0.855460 | 0.301084 | 0.023* | |
C33 | 0.2587 (2) | 0.6909 (3) | 0.30973 (7) | 0.0201 (5) | |
H33 | 0.200010 | 0.731800 | 0.292563 | 0.024* | |
C34 | 0.2513 (2) | 0.5582 (3) | 0.32948 (7) | 0.0204 (5) | |
C35 | 0.3380 (2) | 0.4996 (3) | 0.35461 (8) | 0.0222 (6) | |
H35 | 0.334273 | 0.408341 | 0.368175 | 0.027* | |
C36 | 0.4297 (2) | 0.5747 (3) | 0.35972 (8) | 0.0210 (5) | |
H36 | 0.487955 | 0.534482 | 0.377314 | 0.025* | |
C37 | 0.1256 (2) | 0.4184 (3) | 0.35336 (8) | 0.0213 (5) | |
H37 | 0.163220 | 0.431205 | 0.381049 | 0.026* | |
C38 | 0.03563 (19) | 0.3267 (3) | 0.34722 (8) | 0.0206 (5) | |
C39 | −0.0164 (2) | 0.2972 (3) | 0.30650 (8) | 0.0251 (6) | |
C40 | −0.0959 (2) | 0.1940 (3) | 0.29929 (9) | 0.0313 (7) | |
H40 | −0.130203 | 0.175740 | 0.271316 | 0.038* | |
C41 | −0.1241 (2) | 0.1202 (3) | 0.33190 (9) | 0.0291 (6) | |
H41 | −0.177120 | 0.049838 | 0.326410 | 0.035* | |
C42 | −0.07517 (19) | 0.1470 (3) | 0.37423 (8) | 0.0226 (6) | |
C43 | −0.1041 (2) | 0.0681 (3) | 0.40780 (9) | 0.0261 (6) | |
H43 | −0.155966 | −0.003853 | 0.402031 | 0.031* | |
C44 | −0.0582 (2) | 0.0942 (3) | 0.44851 (9) | 0.0270 (6) | |
H44 | −0.077970 | 0.040511 | 0.470940 | 0.032* | |
C45 | 0.0181 (2) | 0.2004 (3) | 0.45698 (8) | 0.0251 (6) | |
H45 | 0.049100 | 0.219549 | 0.485344 | 0.030* | |
C46 | 0.04883 (19) | 0.2774 (3) | 0.42492 (8) | 0.0224 (6) | |
H46 | 0.101119 | 0.348534 | 0.431445 | 0.027* | |
C47 | 0.00390 (19) | 0.2526 (3) | 0.38229 (8) | 0.0197 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0293 (4) | 0.0315 (4) | 0.0332 (4) | −0.0064 (3) | 0.0033 (3) | −0.0046 (3) |
Cl2 | 0.0444 (5) | 0.0794 (6) | 0.0306 (4) | 0.0072 (5) | 0.0134 (3) | −0.0107 (4) |
C48 | 0.0236 (14) | 0.0201 (13) | 0.0271 (14) | 0.0005 (11) | 0.0013 (11) | 0.0024 (11) |
C49 | 0.0308 (16) | 0.0329 (15) | 0.0242 (14) | 0.0011 (13) | 0.0055 (12) | 0.0021 (12) |
C50 | 0.0237 (16) | 0.0461 (18) | 0.0400 (17) | −0.0019 (14) | 0.0084 (13) | 0.0111 (15) |
C51 | 0.0247 (16) | 0.0341 (16) | 0.0491 (19) | −0.0065 (13) | −0.0049 (14) | 0.0022 (14) |
C52 | 0.0336 (17) | 0.0318 (16) | 0.0348 (16) | 0.0027 (14) | 0.0001 (13) | −0.0051 (13) |
C53 | 0.0285 (15) | 0.0280 (15) | 0.0261 (14) | 0.0018 (12) | 0.0050 (12) | 0.0011 (12) |
O1 | 0.0310 (11) | 0.0256 (10) | 0.0199 (9) | −0.0065 (8) | 0.0056 (8) | 0.0014 (8) |
O2 | 0.0384 (12) | 0.0408 (12) | 0.0223 (10) | −0.0112 (10) | −0.0008 (9) | 0.0044 (9) |
N1 | 0.0253 (12) | 0.0217 (11) | 0.0183 (11) | −0.0013 (10) | 0.0034 (9) | −0.0008 (9) |
N2 | 0.0234 (12) | 0.0219 (11) | 0.0229 (11) | −0.0033 (9) | 0.0070 (9) | −0.0010 (9) |
C1 | 0.0205 (13) | 0.0176 (12) | 0.0180 (12) | −0.0020 (10) | 0.0051 (10) | −0.0012 (10) |
C2 | 0.0178 (13) | 0.0199 (12) | 0.0145 (11) | −0.0048 (10) | −0.0005 (10) | 0.0005 (10) |
C3 | 0.0250 (14) | 0.0224 (13) | 0.0174 (12) | −0.0040 (11) | 0.0029 (11) | −0.0021 (10) |
C4 | 0.0277 (15) | 0.0210 (13) | 0.0254 (14) | −0.0003 (12) | −0.0022 (11) | 0.0007 (11) |
C5 | 0.0307 (16) | 0.0274 (14) | 0.0243 (14) | −0.0057 (13) | −0.0037 (12) | 0.0096 (11) |
C6 | 0.0235 (15) | 0.0335 (15) | 0.0215 (13) | −0.0043 (12) | 0.0049 (11) | 0.0082 (12) |
C7 | 0.0179 (13) | 0.0279 (14) | 0.0157 (12) | −0.0054 (11) | 0.0007 (10) | 0.0010 (10) |
C8 | 0.0165 (13) | 0.0296 (14) | 0.0171 (12) | −0.0036 (11) | 0.0010 (10) | −0.0032 (11) |
C9 | 0.0220 (14) | 0.0409 (16) | 0.0201 (13) | −0.0004 (13) | 0.0058 (11) | 0.0009 (12) |
C10 | 0.0266 (15) | 0.0431 (17) | 0.0260 (14) | 0.0038 (13) | 0.0075 (12) | −0.0091 (13) |
C11 | 0.0270 (15) | 0.0269 (15) | 0.0356 (15) | 0.0006 (12) | 0.0044 (13) | −0.0106 (12) |
C12 | 0.0242 (14) | 0.0223 (13) | 0.0274 (14) | −0.0034 (11) | 0.0055 (11) | −0.0043 (11) |
C13 | 0.0187 (13) | 0.0242 (13) | 0.0171 (12) | −0.0058 (11) | 0.0015 (10) | −0.0049 (10) |
C14 | 0.0252 (14) | 0.0128 (11) | 0.0185 (12) | −0.0045 (10) | 0.0047 (10) | 0.0014 (10) |
C15 | 0.0203 (14) | 0.0215 (13) | 0.0238 (13) | −0.0022 (11) | 0.0037 (11) | −0.0011 (11) |
C16 | 0.0220 (14) | 0.0228 (13) | 0.0213 (13) | −0.0001 (11) | 0.0080 (11) | −0.0011 (10) |
C17 | 0.0213 (14) | 0.0178 (12) | 0.0187 (12) | −0.0014 (11) | 0.0021 (10) | 0.0018 (10) |
C18 | 0.0151 (13) | 0.0229 (13) | 0.0225 (13) | −0.0024 (11) | −0.0004 (10) | 0.0001 (10) |
C19 | 0.0233 (14) | 0.0200 (13) | 0.0212 (13) | −0.0021 (11) | 0.0067 (11) | 0.0003 (10) |
C20 | 0.0215 (14) | 0.0197 (12) | 0.0214 (12) | 0.0023 (11) | 0.0060 (10) | 0.0018 (10) |
C21 | 0.0211 (13) | 0.0192 (12) | 0.0193 (12) | 0.0022 (11) | 0.0037 (10) | −0.0015 (10) |
C22 | 0.0210 (14) | 0.0171 (12) | 0.0225 (13) | 0.0032 (11) | 0.0046 (11) | −0.0020 (10) |
C23 | 0.0295 (15) | 0.0212 (13) | 0.0207 (13) | 0.0042 (12) | 0.0091 (11) | −0.0003 (10) |
C24 | 0.0279 (15) | 0.0263 (14) | 0.0175 (12) | 0.0076 (12) | 0.0034 (11) | −0.0037 (11) |
C25 | 0.0220 (14) | 0.0221 (13) | 0.0240 (13) | 0.0047 (11) | 0.0042 (11) | −0.0051 (11) |
C26 | 0.0247 (15) | 0.0276 (14) | 0.0272 (14) | 0.0028 (12) | −0.0016 (12) | −0.0082 (12) |
C27 | 0.0224 (15) | 0.0267 (14) | 0.0387 (16) | −0.0046 (12) | −0.0001 (12) | −0.0099 (13) |
C28 | 0.0336 (17) | 0.0250 (14) | 0.0368 (16) | −0.0035 (13) | 0.0120 (13) | −0.0006 (12) |
C29 | 0.0285 (15) | 0.0240 (14) | 0.0239 (13) | −0.0012 (12) | 0.0050 (11) | 0.0002 (11) |
C30 | 0.0179 (13) | 0.0189 (12) | 0.0240 (13) | 0.0034 (11) | 0.0037 (10) | −0.0028 (10) |
C31 | 0.0210 (13) | 0.0174 (12) | 0.0156 (12) | 0.0007 (10) | 0.0044 (10) | −0.0041 (10) |
C32 | 0.0255 (14) | 0.0177 (12) | 0.0145 (11) | −0.0022 (11) | 0.0056 (10) | −0.0029 (10) |
C33 | 0.0208 (13) | 0.0226 (13) | 0.0169 (12) | 0.0014 (11) | 0.0034 (10) | −0.0038 (10) |
C34 | 0.0229 (14) | 0.0242 (13) | 0.0157 (12) | −0.0050 (11) | 0.0081 (10) | −0.0055 (10) |
C35 | 0.0262 (14) | 0.0197 (13) | 0.0224 (13) | −0.0015 (11) | 0.0086 (11) | −0.0003 (11) |
C36 | 0.0210 (14) | 0.0218 (13) | 0.0204 (13) | −0.0003 (11) | 0.0041 (10) | 0.0013 (10) |
C37 | 0.0217 (14) | 0.0218 (13) | 0.0209 (13) | 0.0007 (11) | 0.0047 (11) | −0.0031 (10) |
C38 | 0.0190 (13) | 0.0171 (12) | 0.0256 (13) | 0.0008 (11) | 0.0040 (10) | −0.0011 (10) |
C39 | 0.0236 (14) | 0.0264 (14) | 0.0241 (13) | −0.0006 (12) | 0.0012 (11) | 0.0029 (11) |
C40 | 0.0294 (16) | 0.0337 (16) | 0.0267 (14) | −0.0056 (13) | −0.0061 (12) | 0.0005 (12) |
C41 | 0.0228 (15) | 0.0262 (14) | 0.0358 (16) | −0.0067 (12) | −0.0020 (12) | −0.0009 (12) |
C42 | 0.0186 (13) | 0.0202 (13) | 0.0287 (14) | 0.0032 (11) | 0.0035 (11) | −0.0007 (11) |
C43 | 0.0200 (14) | 0.0207 (13) | 0.0384 (16) | −0.0029 (11) | 0.0071 (12) | 0.0008 (12) |
C44 | 0.0282 (15) | 0.0239 (14) | 0.0312 (15) | 0.0008 (12) | 0.0116 (12) | 0.0045 (12) |
C45 | 0.0244 (14) | 0.0265 (14) | 0.0247 (14) | 0.0032 (12) | 0.0051 (11) | −0.0003 (11) |
C46 | 0.0178 (13) | 0.0215 (13) | 0.0285 (14) | −0.0008 (11) | 0.0057 (11) | −0.0027 (11) |
C47 | 0.0150 (13) | 0.0190 (12) | 0.0254 (13) | 0.0017 (10) | 0.0044 (10) | −0.0021 (10) |
Cl1—C48 | 1.730 (3) | C18—H18 | 0.9500 |
Cl2—C49 | 1.736 (3) | C18—C19 | 1.392 (4) |
C48—C49 | 1.387 (4) | C19—H19 | 0.9500 |
C48—C53 | 1.380 (4) | C20—H20 | 0.9500 |
C49—C50 | 1.382 (4) | C20—C21 | 1.451 (3) |
C50—H50 | 0.9500 | C21—C22 | 1.399 (3) |
C50—C51 | 1.383 (4) | C21—C30 | 1.441 (4) |
C51—H51 | 0.9500 | C22—C23 | 1.409 (4) |
C51—C52 | 1.380 (4) | C23—H23 | 0.9500 |
C52—H52 | 0.9500 | C23—C24 | 1.356 (4) |
C52—C53 | 1.385 (4) | C24—H24 | 0.9500 |
C53—H53 | 0.9500 | C24—C25 | 1.418 (4) |
O1—H1 | 0.87 (3) | C25—C26 | 1.411 (4) |
O1—C22 | 1.349 (3) | C25—C30 | 1.430 (4) |
O2—H2 | 1.00 (4) | C26—H26 | 0.9500 |
O2—C39 | 1.351 (3) | C26—C27 | 1.361 (4) |
N1—C17 | 1.422 (3) | C27—H27 | 0.9500 |
N1—C20 | 1.298 (3) | C27—C28 | 1.403 (4) |
N2—C34 | 1.424 (3) | C28—H28 | 0.9500 |
N2—C37 | 1.292 (3) | C28—C29 | 1.368 (4) |
C1—C2 | 1.537 (3) | C29—H29 | 0.9500 |
C1—C13 | 1.542 (3) | C29—C30 | 1.418 (4) |
C1—C14 | 1.541 (3) | C31—C32 | 1.394 (4) |
C1—C31 | 1.531 (3) | C31—C36 | 1.400 (3) |
C2—C3 | 1.384 (4) | C32—H32 | 0.9500 |
C2—C7 | 1.401 (3) | C32—C33 | 1.386 (4) |
C3—H3 | 0.9500 | C33—H33 | 0.9500 |
C3—C4 | 1.395 (4) | C33—C34 | 1.386 (4) |
C4—H4 | 0.9500 | C34—C35 | 1.395 (4) |
C4—C5 | 1.390 (4) | C35—H35 | 0.9500 |
C5—H5 | 0.9500 | C35—C36 | 1.385 (4) |
C5—C6 | 1.384 (4) | C36—H36 | 0.9500 |
C6—H6 | 0.9500 | C37—H37 | 0.9500 |
C6—C7 | 1.388 (4) | C37—C38 | 1.447 (4) |
C7—C8 | 1.464 (4) | C38—C39 | 1.397 (4) |
C8—C9 | 1.399 (4) | C38—C47 | 1.445 (4) |
C8—C13 | 1.403 (4) | C39—C40 | 1.409 (4) |
C9—H9 | 0.9500 | C40—H40 | 0.9500 |
C9—C10 | 1.380 (4) | C40—C41 | 1.358 (4) |
C10—H10 | 0.9500 | C41—H41 | 0.9500 |
C10—C11 | 1.388 (4) | C41—C42 | 1.425 (4) |
C11—H11 | 0.9500 | C42—C43 | 1.411 (4) |
C11—C12 | 1.387 (4) | C42—C47 | 1.420 (4) |
C12—H12 | 0.9500 | C43—H43 | 0.9500 |
C12—C13 | 1.383 (4) | C43—C44 | 1.366 (4) |
C14—C15 | 1.400 (3) | C44—H44 | 0.9500 |
C14—C19 | 1.384 (4) | C44—C45 | 1.399 (4) |
C15—H15 | 0.9500 | C45—H45 | 0.9500 |
C15—C16 | 1.388 (4) | C45—C46 | 1.373 (4) |
C16—H16 | 0.9500 | C46—H46 | 0.9500 |
C16—C17 | 1.383 (4) | C46—C47 | 1.416 (4) |
C17—C18 | 1.392 (4) | ||
C49—C48—Cl1 | 120.7 (2) | N1—C20—C21 | 121.6 (2) |
C53—C48—Cl1 | 118.9 (2) | C21—C20—H20 | 119.2 |
C53—C48—C49 | 120.4 (3) | C22—C21—C20 | 119.2 (2) |
C48—C49—Cl2 | 120.8 (2) | C22—C21—C30 | 118.9 (2) |
C50—C49—Cl2 | 119.7 (2) | C30—C21—C20 | 121.6 (2) |
C50—C49—C48 | 119.5 (3) | O1—C22—C21 | 121.8 (2) |
C49—C50—H50 | 119.9 | O1—C22—C23 | 117.1 (2) |
C49—C50—C51 | 120.2 (3) | C21—C22—C23 | 121.1 (2) |
C51—C50—H50 | 119.9 | C22—C23—H23 | 119.9 |
C50—C51—H51 | 119.9 | C24—C23—C22 | 120.1 (2) |
C52—C51—C50 | 120.1 (3) | C24—C23—H23 | 119.9 |
C52—C51—H51 | 119.9 | C23—C24—H24 | 119.0 |
C51—C52—H52 | 120.0 | C23—C24—C25 | 122.0 (2) |
C51—C52—C53 | 120.0 (3) | C25—C24—H24 | 119.0 |
C53—C52—H52 | 120.0 | C24—C25—C30 | 118.6 (2) |
C48—C53—C52 | 119.8 (3) | C26—C25—C24 | 121.6 (2) |
C48—C53—H53 | 120.1 | C26—C25—C30 | 119.8 (2) |
C52—C53—H53 | 120.1 | C25—C26—H26 | 119.4 |
C22—O1—H1 | 109 (2) | C27—C26—C25 | 121.3 (3) |
C39—O2—H2 | 104.5 (19) | C27—C26—H26 | 119.4 |
C20—N1—C17 | 120.8 (2) | C26—C27—H27 | 120.3 |
C37—N2—C34 | 119.3 (2) | C26—C27—C28 | 119.4 (3) |
C2—C1—C13 | 100.94 (19) | C28—C27—H27 | 120.3 |
C2—C1—C14 | 107.63 (19) | C27—C28—H28 | 119.5 |
C14—C1—C13 | 113.3 (2) | C29—C28—C27 | 121.0 (3) |
C31—C1—C2 | 113.5 (2) | C29—C28—H28 | 119.5 |
C31—C1—C13 | 111.35 (19) | C28—C29—H29 | 119.3 |
C31—C1—C14 | 109.93 (19) | C28—C29—C30 | 121.4 (3) |
C3—C2—C1 | 129.0 (2) | C30—C29—H29 | 119.3 |
C3—C2—C7 | 120.4 (2) | C25—C30—C21 | 119.2 (2) |
C7—C2—C1 | 110.6 (2) | C29—C30—C21 | 123.8 (2) |
C2—C3—H3 | 120.6 | C29—C30—C25 | 117.0 (2) |
C2—C3—C4 | 118.8 (2) | C32—C31—C1 | 123.3 (2) |
C4—C3—H3 | 120.6 | C32—C31—C36 | 117.2 (2) |
C3—C4—H4 | 119.7 | C36—C31—C1 | 119.5 (2) |
C5—C4—C3 | 120.6 (3) | C31—C32—H32 | 119.3 |
C5—C4—H4 | 119.7 | C33—C32—C31 | 121.5 (2) |
C4—C5—H5 | 119.7 | C33—C32—H32 | 119.3 |
C6—C5—C4 | 120.7 (2) | C32—C33—H33 | 119.8 |
C6—C5—H5 | 119.7 | C34—C33—C32 | 120.5 (2) |
C5—C6—H6 | 120.5 | C34—C33—H33 | 119.8 |
C5—C6—C7 | 119.0 (2) | C33—C34—N2 | 118.9 (2) |
C7—C6—H6 | 120.5 | C33—C34—C35 | 119.1 (2) |
C2—C7—C8 | 109.0 (2) | C35—C34—N2 | 121.9 (2) |
C6—C7—C2 | 120.6 (2) | C34—C35—H35 | 120.1 |
C6—C7—C8 | 130.4 (2) | C36—C35—C34 | 119.8 (2) |
C9—C8—C7 | 130.8 (2) | C36—C35—H35 | 120.1 |
C9—C8—C13 | 120.3 (2) | C31—C36—H36 | 119.1 |
C13—C8—C7 | 108.9 (2) | C35—C36—C31 | 121.9 (2) |
C8—C9—H9 | 120.5 | C35—C36—H36 | 119.1 |
C10—C9—C8 | 119.0 (3) | N2—C37—H37 | 119.0 |
C10—C9—H9 | 120.5 | N2—C37—C38 | 121.9 (2) |
C9—C10—H10 | 119.8 | C38—C37—H37 | 119.0 |
C9—C10—C11 | 120.4 (3) | C39—C38—C37 | 120.0 (2) |
C11—C10—H10 | 119.8 | C39—C38—C47 | 118.6 (2) |
C10—C11—H11 | 119.5 | C47—C38—C37 | 121.1 (2) |
C10—C11—C12 | 121.0 (3) | O2—C39—C38 | 121.9 (2) |
C12—C11—H11 | 119.5 | O2—C39—C40 | 116.9 (2) |
C11—C12—H12 | 120.4 | C38—C39—C40 | 121.1 (2) |
C13—C12—C11 | 119.2 (3) | C39—C40—H40 | 119.7 |
C13—C12—H12 | 120.4 | C41—C40—C39 | 120.7 (2) |
C8—C13—C1 | 110.5 (2) | C41—C40—H40 | 119.7 |
C12—C13—C1 | 129.5 (2) | C40—C41—H41 | 119.6 |
C12—C13—C8 | 120.0 (2) | C40—C41—C42 | 120.9 (3) |
C15—C14—C1 | 119.2 (2) | C42—C41—H41 | 119.6 |
C19—C14—C1 | 122.6 (2) | C43—C42—C41 | 120.4 (2) |
C19—C14—C15 | 118.1 (2) | C43—C42—C47 | 120.3 (2) |
C14—C15—H15 | 119.6 | C47—C42—C41 | 119.4 (2) |
C16—C15—C14 | 120.7 (2) | C42—C43—H43 | 119.7 |
C16—C15—H15 | 119.6 | C44—C43—C42 | 120.7 (2) |
C15—C16—H16 | 119.7 | C44—C43—H43 | 119.7 |
C17—C16—C15 | 120.6 (2) | C43—C44—H44 | 120.2 |
C17—C16—H16 | 119.7 | C43—C44—C45 | 119.6 (2) |
C16—C17—N1 | 118.3 (2) | C45—C44—H44 | 120.2 |
C16—C17—C18 | 119.2 (2) | C44—C45—H45 | 119.5 |
C18—C17—N1 | 122.4 (2) | C46—C45—C44 | 121.0 (2) |
C17—C18—H18 | 120.0 | C46—C45—H45 | 119.5 |
C17—C18—C19 | 120.0 (2) | C45—C46—H46 | 119.4 |
C19—C18—H18 | 120.0 | C45—C46—C47 | 121.1 (2) |
C14—C19—C18 | 121.4 (2) | C47—C46—H46 | 119.4 |
C14—C19—H19 | 119.3 | C42—C47—C38 | 119.2 (2) |
C18—C19—H19 | 119.3 | C46—C47—C38 | 123.5 (2) |
N1—C20—H20 | 119.2 | C46—C47—C42 | 117.3 (2) |
Cl1—C48—C49—Cl2 | −1.1 (3) | C15—C16—C17—C18 | −3.0 (4) |
Cl1—C48—C49—C50 | −179.7 (2) | C16—C17—C18—C19 | 1.8 (4) |
Cl1—C48—C53—C52 | 178.5 (2) | C17—N1—C20—C21 | −174.0 (2) |
Cl2—C49—C50—C51 | −177.9 (2) | C17—C18—C19—C14 | 0.7 (4) |
C48—C49—C50—C51 | 0.7 (5) | C19—C14—C15—C16 | 0.7 (4) |
C49—C48—C53—C52 | −1.4 (4) | C20—N1—C17—C16 | −136.1 (3) |
C49—C50—C51—C52 | −0.4 (5) | C20—N1—C17—C18 | 47.7 (3) |
C50—C51—C52—C53 | −0.9 (5) | C20—C21—C22—O1 | −5.1 (4) |
C51—C52—C53—C48 | 1.7 (4) | C20—C21—C22—C23 | 172.9 (2) |
C53—C48—C49—Cl2 | 178.8 (2) | C20—C21—C30—C25 | −170.8 (2) |
C53—C48—C49—C50 | 0.2 (4) | C20—C21—C30—C29 | 8.7 (4) |
O1—C22—C23—C24 | 177.0 (2) | C21—C22—C23—C24 | −1.1 (4) |
O2—C39—C40—C41 | 178.3 (3) | C22—C21—C30—C25 | 3.2 (4) |
N1—C17—C18—C19 | 177.9 (2) | C22—C21—C30—C29 | −177.3 (2) |
N1—C20—C21—C22 | 7.6 (4) | C22—C23—C24—C25 | 1.4 (4) |
N1—C20—C21—C30 | −178.4 (2) | C23—C24—C25—C26 | −179.9 (2) |
N2—C34—C35—C36 | 178.1 (2) | C23—C24—C25—C30 | 0.6 (4) |
N2—C37—C38—C39 | 5.0 (4) | C24—C25—C26—C27 | −179.4 (3) |
N2—C37—C38—C47 | 178.7 (2) | C24—C25—C30—C21 | −2.9 (4) |
C1—C2—C3—C4 | 179.5 (2) | C24—C25—C30—C29 | 177.6 (2) |
C1—C2—C7—C6 | 179.8 (2) | C25—C26—C27—C28 | 2.0 (4) |
C1—C2—C7—C8 | 0.0 (3) | C26—C25—C30—C21 | 177.6 (2) |
C1—C14—C15—C16 | −175.1 (2) | C26—C25—C30—C29 | −1.9 (4) |
C1—C14—C19—C18 | 173.7 (2) | C26—C27—C28—C29 | −2.2 (4) |
C1—C31—C32—C33 | −179.0 (2) | C27—C28—C29—C30 | 0.2 (4) |
C1—C31—C36—C35 | 179.6 (2) | C28—C29—C30—C21 | −177.7 (2) |
C2—C1—C13—C8 | 0.7 (3) | C28—C29—C30—C25 | 1.8 (4) |
C2—C1—C13—C12 | −178.8 (3) | C30—C21—C22—O1 | −179.2 (2) |
C2—C1—C14—C15 | 86.6 (3) | C30—C21—C22—C23 | −1.2 (4) |
C2—C1—C14—C19 | −89.0 (3) | C30—C25—C26—C27 | 0.1 (4) |
C2—C1—C31—C32 | 3.0 (3) | C31—C1—C2—C3 | 61.9 (3) |
C2—C1—C31—C36 | −175.3 (2) | C31—C1—C2—C7 | −119.6 (2) |
C2—C3—C4—C5 | −0.2 (4) | C31—C1—C13—C8 | 121.5 (2) |
C2—C7—C8—C9 | −179.5 (3) | C31—C1—C13—C12 | −58.1 (3) |
C2—C7—C8—C13 | 0.5 (3) | C31—C1—C14—C15 | −37.4 (3) |
C3—C2—C7—C6 | −1.7 (4) | C31—C1—C14—C19 | 147.0 (2) |
C3—C2—C7—C8 | 178.5 (2) | C31—C32—C33—C34 | 0.1 (4) |
C3—C4—C5—C6 | −0.5 (4) | C32—C31—C36—C35 | 1.2 (3) |
C4—C5—C6—C7 | 0.1 (4) | C32—C33—C34—N2 | −177.7 (2) |
C5—C6—C7—C2 | 1.0 (4) | C32—C33—C34—C35 | 0.0 (3) |
C5—C6—C7—C8 | −179.3 (3) | C33—C34—C35—C36 | 0.5 (4) |
C6—C7—C8—C9 | 0.7 (5) | C34—N2—C37—C38 | −172.8 (2) |
C6—C7—C8—C13 | −179.2 (3) | C34—C35—C36—C31 | −1.1 (4) |
C7—C2—C3—C4 | 1.2 (4) | C36—C31—C32—C33 | −0.7 (3) |
C7—C8—C9—C10 | −179.4 (3) | C37—N2—C34—C33 | −139.8 (2) |
C7—C8—C13—C1 | −0.8 (3) | C37—N2—C34—C35 | 42.6 (3) |
C7—C8—C13—C12 | 178.8 (2) | C37—C38—C39—O2 | −6.4 (4) |
C8—C9—C10—C11 | 0.4 (4) | C37—C38—C39—C40 | 171.8 (2) |
C9—C8—C13—C1 | 179.2 (2) | C37—C38—C47—C42 | −170.6 (2) |
C9—C8—C13—C12 | −1.1 (4) | C37—C38—C47—C46 | 8.2 (4) |
C9—C10—C11—C12 | −0.8 (4) | C38—C39—C40—C41 | 0.0 (4) |
C10—C11—C12—C13 | 0.2 (4) | C39—C38—C47—C42 | 3.3 (4) |
C11—C12—C13—C1 | −179.7 (2) | C39—C38—C47—C46 | −177.9 (2) |
C11—C12—C13—C8 | 0.8 (4) | C39—C40—C41—C42 | 1.0 (4) |
C13—C1—C2—C3 | −178.8 (2) | C40—C41—C42—C43 | −179.0 (3) |
C13—C1—C2—C7 | −0.4 (3) | C40—C41—C42—C47 | 0.2 (4) |
C13—C1—C14—C15 | −162.7 (2) | C41—C42—C43—C44 | −179.4 (3) |
C13—C1—C14—C19 | 21.7 (3) | C41—C42—C47—C38 | −2.3 (4) |
C13—C1—C31—C32 | −110.1 (3) | C41—C42—C47—C46 | 178.8 (2) |
C13—C1—C31—C36 | 71.6 (3) | C42—C43—C44—C45 | 0.1 (4) |
C13—C8—C9—C10 | 0.5 (4) | C43—C42—C47—C38 | 176.9 (2) |
C14—C1—C2—C3 | −59.9 (3) | C43—C42—C47—C46 | −2.0 (4) |
C14—C1—C2—C7 | 118.5 (2) | C43—C44—C45—C46 | −1.1 (4) |
C14—C1—C13—C8 | −114.0 (2) | C44—C45—C46—C47 | 0.4 (4) |
C14—C1—C13—C12 | 66.4 (3) | C45—C46—C47—C38 | −177.8 (2) |
C14—C1—C31—C32 | 123.5 (2) | C45—C46—C47—C42 | 1.1 (4) |
C14—C1—C31—C36 | −54.7 (3) | C47—C38—C39—O2 | 179.7 (2) |
C14—C15—C16—C17 | 1.7 (4) | C47—C38—C39—C40 | −2.1 (4) |
C15—C14—C19—C18 | −2.0 (4) | C47—C42—C43—C44 | 1.4 (4) |
C15—C16—C17—N1 | −179.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.87 (3) | 1.75 (3) | 2.526 (3) | 148 (3) |
O2—H2···N2 | 1.00 (4) | 1.63 (4) | 2.558 (3) | 152 (3) |
C3—H3···O1i | 0.95 | 2.58 | 3.461 (3) | 155 |
C35—H35···O1ii | 0.95 | 2.44 | 3.389 (3) | 178 |
C28—H28···Cl1iii | 0.95 | 2.86 | 3.770 (3) | 161 |
C45—H45···Cl1ii | 0.95 | 2.86 | 3.457 (3) | 122 |
C46—H46···Cl1ii | 0.95 | 2.88 | 3.465 (3) | 121 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+2, −y+2, −z+1. |
Acknowledgements
The X-ray diffraction studies were performed at the Shared Equipment Center of the Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences.
Funding information
This work was performed under the support of the FRCCP RAS State task AAAA-A19–119012990175-9. We acknowledge the RUDN University Program 5–100 and the Ministry of Science and Higher Education of the Russian Federation [grant No. 075–03-2020–223 (FSSF-2020–0017)].
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