research communications
μ-2-methoxy-6-[(methylimino)methyl]phenolato}bis({2-methoxy-6-[(methylimino)methyl]phenolato}nickel(II)) involving different coordination modes of the same Schiff base ligand
of bis{aDepartment of Chemistry, Taras Shevchenko National University of Kyiv, 64/13 Volodymyrska Street, Kyiv 01601, Ukraine, and bSchool of Molecular Sciences, M310, University of Western Australia, Perth, WA 6009, Australia
*Correspondence e-mail: vassilyeva@univ.kiev.ua
The structure of the title compound, [Ni2(C9H10NO2)4], is built up by discrete centrosymmetric dimers. Two nitrogen and three oxygen atoms of two Schiff base ligands singly deprotonated at the phenolate site form a square-pyramidal environment for each metal atom. The ligands are bonded differently to the metal centre: one of the phenolic O atoms is bound to one nickel atom, whereas another bridges the two metal atoms to form the dimer. The Ni—N/O distances fall in the range 1.8965 (13)–1.9926 (15) Å, with the Ni—N bonds being slightly longer; the fifth contact of the metal to the bridging phenolate oxygen atom is substantially elongated [2.533 (1) Å]. A similar coordination geometry was observed in the isomorphous Cu analogue previously reported by us [Sydoruk et al. (2013). Acta Cryst. E69, m551–m552]. In the crystal, the [Ni2L4] molecules form sheets parallel to the ab plane with the polar methoxy groups protruding into the intersheet space and keeping the sheets apart. Within a sheet, the molecules are stacked relative to each other in such a way that the Ni2O2 planes of neighbouring molecules are orthogonal.
Keywords: crystal structure; NiII dimer; Schiff base ligand; o-vanillin; methylamine.
CCDC reference: 1908788
1. Chemical context
The title compound, [Ni2(C9H10NO2)4], 1, has been synthesized as part of our long-term research on Schiff base metal complexes aimed at the preparation of mono- and heterometallic compounds of various compositions and structures, and the investigation of their potential applications. In these studies, we use direct synthesis of coordination compounds based on a spontaneous self-assembly in solution, in which the metal (or one of the metals in the case of heterometallic complexes) is introduced as a fine powder (zerovalent state) and oxidized by aerial dioxygen during the synthesis (Buvaylo et al., 2005, 2012; Kokozay et al., 2018).
The multidentate ligand 2-methoxy-6-[(methylimino)methyl]phenol, HL, derived from 2-hydroxy-3-methoxy-benzaldehyde (o-vanillin) and methylamine shows various connectivity fashions and can generate mono- and polymetallic complexes. The methoxy group plays an essential role in the coordination abilities of the Schiff base (Andruh, 2015). The singly deprotonated HL ligand has been shown to act as a multidentate linker between seven metal centres affording [M7] assemblies, where M is a divalent Ni, Zn, Co or Mn ion (Meally et al., 2010, 2012; Zhang et al., 2010). The octahedral metal atoms in the heptanuclear cores are additionally supported by μ3-bridging OH− or MeO− groups that link the central metal atom to the six peripheral ones. Of heterometallic examples with HL, only four 1s–3d structures of Na/M (M = Fe, Ni) complexes have been reported (Meally et al., 2013).
Our research efforts in the field have yielded novel heterometallic dinuclear CoIII/Cd and CoIII/Zn complexes bearing HL along with the `parent' mononuclear complex CoL3·DMF (DMF = N,N-dimethylformamide; Nesterova et al., 2018, 2019; Vassilyeva et al., 2018). Their in stereospecific oxidation with m-chloroperbenzoic acid as an oxidant has been studied in detail. A comparison of the catalytic behaviours of the hetero- and monometallic analogues provided further insight into the origin of stereoselectivity of the oxidation of C—H bonds. In the syntheses, the condensation reaction between o-vanillin and CH3NH2·HCl was utilized without isolation of the resulting Schiff base. In the present work, the title compound was isolated in an attempt to prepare a heterometallic Ni/Sn complex with HL in the reaction of nickel powder and SnCl2·2H2O, with the Schiff base formed in situ in a methanol/DMF mixture in a 1:1:2 molar ratio. Similarly to the synthesis of CoL3·DMF (Nesterova et al., 2018), HL does not enable the formation of a heterometallic Sn-containing species, in contrast to its compartmental analogues 3-R-salicylaldehyde-ethylenediamine (R = methoxy-, ethoxy-), HL′, that afford heterometallic, diphenoxido-bridged, dinuclear CuIISnII cations [CuL′SnCl]+ (Hazra et al., 2016).
2. Structural commentary
The molecular structure of 1 exists as a centrosymmetric dimer [Ni2L4] (Fig. 1). The nickel atom is five-coordinate with two nitrogen and three oxygen atoms of two, singly deprotonated at the phenolate site Schiff base ligands. The ligands are bonded differently to the metal atoms: the phenolic oxygen atom O21 is bound to one nickel atom, whereas O11 bridges the two metal centres and forms the dimer.
The Ni—N bonds are somewhat longer than the shortest Ni—O distances (Table 1) while the fifth contact of the metal to the bridging oxygen atom is substantially elongated. The cis angles at the nickel atom are in the range 87.57 (6)–91.09 (6)°, with the two trans angles being 170.92 (6) and 175.66 (6)° (Table 1). The angular structural index parameter, τ = (β – α)/60, evaluated from the two largest angles (α < β) in the five-coordinate geometry is 0.08 compared with ideal values of 1 for an equilateral bipyramid and 0 for a square pyramid. Hence, the nickel in 1 is a square pyramid with minimal distortion. The apical position of the coordination sphere is occupied by the bridging phenolate oxygen O11(1 − x, 1 − y, 1 − z) with a bridging angle of 101.44 (2)°.
We reported a similar coordination geometry for the isomorphous Cu analogue [Cu2L4; Sydoruk et al., 2013]. The main difference between the two structures is the proximity of the metal centres in the dimers, which are further apart in the Ni complex compared to the Cu compound. The Ni⋯Ni distance is 3.4638 (4) compared to the Cu⋯Cu separation of 3.3737 (2) Å. In addition, the Cu—O11(1 − x, 1 − y, 1 − z) contact in [Cu2L4] is shorter [2.4329 (7) Å].
3. Supramolecular features
There are no significant intermolecular interactions between the dimers in the 1. The molecules form sheets parallel to the ab plane with the non-coordinating polar methoxy groups protruding into the intersheet space and keeping the sheets apart (Fig. 2). Within a sheet, the molecules pack relative to each other in such a way that neighbouring Ni2O2 planes are orthogonal (Fig. 3). The minimum Ni⋯Ni separations inside a sheet and between adjacent sheets are about 7.099 and 11.374 Å, respectively. The C—H⋯O interaction between C28—H28A and O22(x + , −y + , −z + 1) [C28—H28A = 0.98 Å, H28A⋯O22 = 2.57 Å, C28⋯O22 = 3.449 (2) Å and C28—H28A⋯O22 = 150°] is very weak.
Classical hydrogen-bonding interactions are absent in4. Database survey
A search in the Cambridge Structural Database (CSD; Groom et al., 2016) for HL and its complexes via the WebCSD interface in March 2019 reveals that 39 original crystal structures, including the structure of the ligand itself, have been reported. Polynuclear complexes constitute the majority of the structures with 17 examples of [MII7] (M = Mn, Co, Ni, Zn) assemblies featuring planar hexagonal disc-like cores and three examples of dimeric (Cu2) and tetrameric complexes with the cubane- (Mn4) or open-cubane type cores (Co4). The singly deprotonated HL ligand evidently encourages the formation of polynuclear metal complexes only with assistance from other bridging ligands. The integrity of the hepta- [MII7L6] and tetranuclear [Mn4L3], [Co4L2] polymetallics is secured by μ3-bridging OH−/MeO− groups and other ligands, respectively. A higher metal-to-ligand ratio (1:2 and 1:3) in the absence of bridging ligands stimulates the formation of mononuclear complexes, as evidenced by the 10 structures with molecular (Mn, Co and Pt) or polymeric (Mn) arrangements in the The four heterometallic examples with HL published by others are limited to Na/M (M = Fe, Ni) complexes whose formation was induced by the use of sodium salts and/or NaOH in the synthesis. The 3d–3d/4d heterometallics recently reported by our group are based on the neutral CoIIIL3 species with the metal centre in a mer configuration that acts as a metalloligand to Zn2+/Cd2+ ions, generating [CoML3Cl2]·Solv (Solv = H2O, CH3OH) complexes.
5. Synthesis and crystallization
o-Vanillin (0.3 g, 2.0 mmol) in 10 mL of methanol was stirred with CH3NH2·HCl (0.14 g, 2.0 mmol) in the presence of dimethylaminoethanol (0.1 mL) in a 50 mL conical flask at 333 K for half an hour. SnCl2·2H2O (0.23 g, 1.0 mmol) dissolved in 10 mL of DMF and Ni powder (0.06 g, 1.0 mmol) were added to the resulting yellow solution of the preformed Schiff base. The mixture gradually turned brown while it was magnetically stirred at 333 K to achieve dissolution of the nickel (2 h; adhesion of a small fraction of the metal particles to the stirring bar precluded complete dissolution of the metal powder). The resultant brown solution was filtered and left to stand at room temperature. Dark-brown, almost black, prisms of 1 formed in two weeks. They were filtered off, washed with dry PriOH and dried in air. Yield (based on Ni): 31%. Analysis calculated for C36H40N4Ni2O8 (774.14): C 55.86, H 5.21, N 7.24%. Found: C 55.62, H 5.33, N 7.11%.
A broad band centered at about 3440 cm−1 in the IR spectrum of 1 may be due to adsorbed water molecules (Fig. 4). Several bands arising above and below 3000 cm−1 are assigned to aromatic =CH and alkyl –CH stretching, respectively. The characteristic ν(C=N) absorption of the Schiff base which appears at 1634 cm−1 as a strong intense band in the IR spectrum of HL (Nesterova et al., 2018) is detected at 1630 cm−1 in the spectrum of 1. A number of sharp and intense bands are observed in the aromatic ring stretching (1600–1400 cm−1) and C—H out-of-plane bending regions (800–700 cm−1).
6. Refinement
Crystal data, data collection and structure . Hydrogen atoms were placed at idealized positions and refined using a riding model: C—H = 0.95 Å with Uiso(H) = 1.2Ueq(C) for CH, 0.98 Å and 1.5Ueq(C) for CH3.
details are summarized in Table 2
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Supporting information
CCDC reference: 1908788
https://doi.org/10.1107/S2056989019004766/lh5898sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019004766/lh5898Isup2.hkl
Data collection: CrysAlis PRO (Rigaku OD, 2015); cell
CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg, 1999) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 2012).[Ni2(C9H10NO2)4] | F(000) = 1616 |
Mr = 774.14 | Dx = 1.53 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 6602 reflections |
a = 10.2301 (2) Å | θ = 2.6–31.7° |
b = 15.2456 (3) Å | µ = 1.18 mm−1 |
c = 21.5426 (5) Å | T = 100 K |
V = 3359.87 (12) Å3 | Prism, black |
Z = 4 | 0.37 × 0.27 × 0.23 mm |
Oxford Diffraction Xcalibur diffractometer | 5548 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 4332 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
Detector resolution: 16.0009 pixels mm-1 | θmax = 32.1°, θmin = 2.6° |
ω scans | h = −15→12 |
Absorption correction: analytical (CrysAlis PRO; Rigaku OD, 2015) | k = −22→22 |
Tmin = 0.816, Tmax = 0.87 | l = −29→32 |
20556 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.088 | w = 1/[σ2(Fo2) + (0.0253P)2 + 2.4148P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.002 |
5548 reflections | Δρmax = 0.89 e Å−3 |
230 parameters | Δρmin = −0.61 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. Three low theta reflections, considered to be partly hidden by the beam stop were omitted from the refnement. |
x | y | z | Uiso*/Ueq | ||
Ni1 | 0.40070 (2) | 0.58979 (2) | 0.51420 (2) | 0.01932 (7) | |
C11 | 0.32402 (17) | 0.46376 (12) | 0.42138 (9) | 0.0242 (4) | |
O11 | 0.41820 (12) | 0.50907 (10) | 0.44669 (6) | 0.0315 (3) | |
C12 | 0.33944 (18) | 0.43535 (12) | 0.35897 (9) | 0.0250 (4) | |
O12 | 0.45143 (13) | 0.46517 (10) | 0.33106 (6) | 0.0330 (3) | |
C121 | 0.4805 (2) | 0.43159 (15) | 0.27123 (9) | 0.0363 (5) | |
H12A | 0.4893 | 0.3677 | 0.2735 | 0.054* | |
H12B | 0.5626 | 0.4572 | 0.2563 | 0.054* | |
H12C | 0.4097 | 0.4467 | 0.2425 | 0.054* | |
C13 | 0.2460 (2) | 0.38443 (12) | 0.33055 (9) | 0.0292 (4) | |
H13 | 0.2578 | 0.3661 | 0.2888 | 0.035* | |
C14 | 0.1331 (2) | 0.35947 (13) | 0.36323 (10) | 0.0331 (4) | |
H14 | 0.0691 | 0.3238 | 0.3436 | 0.04* | |
C15 | 0.11502 (19) | 0.38630 (13) | 0.42312 (10) | 0.0295 (4) | |
H15 | 0.0384 | 0.3692 | 0.4449 | 0.035* | |
C16 | 0.20898 (17) | 0.43913 (12) | 0.45289 (9) | 0.0243 (4) | |
C17 | 0.18436 (17) | 0.46528 (12) | 0.51630 (9) | 0.0253 (4) | |
H17 | 0.1124 | 0.4384 | 0.5366 | 0.03* | |
N17 | 0.25052 (14) | 0.52145 (10) | 0.54782 (7) | 0.0252 (3) | |
C18 | 0.21030 (18) | 0.53585 (14) | 0.61258 (9) | 0.0292 (4) | |
H18A | 0.1355 | 0.4981 | 0.6223 | 0.044* | |
H18B | 0.1854 | 0.5974 | 0.6182 | 0.044* | |
H18C | 0.2832 | 0.5216 | 0.6404 | 0.044* | |
C21 | 0.44702 (17) | 0.73584 (11) | 0.59655 (9) | 0.0231 (3) | |
O21 | 0.37097 (12) | 0.67232 (8) | 0.57853 (6) | 0.0262 (3) | |
C22 | 0.41501 (17) | 0.78091 (12) | 0.65278 (9) | 0.0247 (4) | |
O22 | 0.30458 (13) | 0.75045 (9) | 0.68192 (6) | 0.0277 (3) | |
C221 | 0.2536 (2) | 0.80316 (14) | 0.73071 (10) | 0.0360 (5) | |
H22A | 0.3158 | 0.8041 | 0.7653 | 0.054* | |
H22B | 0.1703 | 0.7786 | 0.7449 | 0.054* | |
H22C | 0.2398 | 0.8631 | 0.7156 | 0.054* | |
C23 | 0.49076 (19) | 0.84910 (12) | 0.67430 (9) | 0.0296 (4) | |
H23 | 0.4677 | 0.878 | 0.7118 | 0.036* | |
C24 | 0.6015 (2) | 0.87618 (14) | 0.64127 (10) | 0.0337 (4) | |
H24 | 0.6537 | 0.9231 | 0.6564 | 0.04* | |
C25 | 0.63413 (19) | 0.83488 (13) | 0.58706 (10) | 0.0311 (4) | |
H25 | 0.7094 | 0.8534 | 0.5648 | 0.037* | |
C26 | 0.55760 (17) | 0.76490 (12) | 0.56357 (9) | 0.0246 (4) | |
C27 | 0.58830 (17) | 0.73171 (12) | 0.50282 (9) | 0.0257 (4) | |
H27 | 0.6594 | 0.7585 | 0.4817 | 0.031* | |
N27 | 0.52852 (14) | 0.66906 (10) | 0.47419 (7) | 0.0249 (3) | |
C28 | 0.5641 (2) | 0.65577 (14) | 0.40857 (9) | 0.0334 (4) | |
H28A | 0.6369 | 0.6946 | 0.3977 | 0.05* | |
H28B | 0.4887 | 0.6692 | 0.3822 | 0.05* | |
H28C | 0.5903 | 0.5946 | 0.4022 | 0.05* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.01748 (10) | 0.02415 (12) | 0.01631 (11) | −0.00316 (8) | 0.00124 (8) | 0.00016 (9) |
C11 | 0.0218 (8) | 0.0283 (9) | 0.0225 (9) | 0.0008 (7) | −0.0043 (7) | 0.0013 (7) |
O11 | 0.0250 (6) | 0.0462 (8) | 0.0233 (7) | −0.0070 (6) | 0.0005 (5) | −0.0058 (6) |
C12 | 0.0260 (8) | 0.0253 (8) | 0.0235 (9) | 0.0055 (7) | −0.0028 (7) | 0.0005 (7) |
O12 | 0.0292 (7) | 0.0466 (9) | 0.0232 (7) | 0.0010 (6) | 0.0023 (6) | −0.0065 (6) |
C121 | 0.0437 (12) | 0.0427 (12) | 0.0225 (9) | 0.0090 (9) | 0.0033 (9) | −0.0015 (9) |
C13 | 0.0371 (10) | 0.0243 (9) | 0.0263 (10) | 0.0040 (7) | −0.0050 (8) | −0.0022 (8) |
C14 | 0.0391 (11) | 0.0263 (9) | 0.0340 (11) | −0.0055 (8) | −0.0094 (9) | −0.0005 (8) |
C15 | 0.0298 (9) | 0.0275 (9) | 0.0311 (10) | −0.0062 (7) | −0.0043 (8) | 0.0032 (8) |
C16 | 0.0254 (8) | 0.0239 (8) | 0.0235 (9) | −0.0002 (7) | −0.0036 (7) | 0.0021 (7) |
C17 | 0.0222 (8) | 0.0292 (9) | 0.0246 (9) | −0.0029 (7) | −0.0016 (7) | 0.0057 (8) |
N17 | 0.0221 (7) | 0.0320 (8) | 0.0215 (7) | −0.0002 (6) | 0.0008 (6) | 0.0027 (7) |
C18 | 0.0282 (9) | 0.0369 (10) | 0.0226 (9) | −0.0044 (8) | 0.0052 (8) | 0.0008 (8) |
C21 | 0.0227 (8) | 0.0196 (8) | 0.0270 (9) | 0.0020 (6) | −0.0019 (7) | 0.0053 (7) |
O21 | 0.0263 (6) | 0.0241 (6) | 0.0283 (7) | −0.0038 (5) | 0.0065 (5) | −0.0033 (6) |
C22 | 0.0272 (9) | 0.0218 (8) | 0.0252 (9) | 0.0022 (7) | −0.0024 (7) | 0.0041 (7) |
O22 | 0.0313 (7) | 0.0264 (6) | 0.0254 (7) | 0.0015 (5) | 0.0054 (6) | −0.0020 (6) |
C221 | 0.0481 (12) | 0.0317 (10) | 0.0282 (10) | 0.0063 (9) | 0.0075 (10) | −0.0017 (9) |
C23 | 0.0392 (10) | 0.0225 (9) | 0.0272 (10) | 0.0011 (8) | −0.0074 (8) | 0.0022 (8) |
C24 | 0.0386 (11) | 0.0272 (9) | 0.0353 (11) | −0.0077 (8) | −0.0101 (9) | 0.0045 (9) |
C25 | 0.0279 (9) | 0.0288 (9) | 0.0367 (11) | −0.0065 (7) | −0.0041 (8) | 0.0099 (9) |
C26 | 0.0236 (8) | 0.0211 (8) | 0.0293 (9) | 0.0004 (6) | −0.0025 (7) | 0.0065 (7) |
C27 | 0.0209 (8) | 0.0231 (8) | 0.0331 (10) | 0.0026 (6) | 0.0033 (7) | 0.0060 (8) |
N27 | 0.0245 (7) | 0.0233 (7) | 0.0270 (8) | 0.0044 (6) | 0.0039 (6) | 0.0055 (6) |
C28 | 0.0402 (11) | 0.0292 (10) | 0.0307 (10) | 0.0035 (8) | 0.0129 (9) | 0.0047 (8) |
Ni1—O21 | 1.8965 (13) | C18—H18B | 0.98 |
Ni1—O11 | 1.9135 (14) | C18—H18C | 0.98 |
Ni1—N27 | 1.9783 (15) | C21—O21 | 1.302 (2) |
Ni1—N17 | 1.9926 (15) | C21—C26 | 1.407 (2) |
Ni1—O11i | 2.5326 (14) | C21—C22 | 1.431 (3) |
C11—O11 | 1.305 (2) | C22—O22 | 1.373 (2) |
C11—C16 | 1.410 (3) | C22—C23 | 1.377 (3) |
C11—C12 | 1.421 (3) | O22—C221 | 1.422 (2) |
C12—O12 | 1.371 (2) | C221—H22A | 0.98 |
C12—C13 | 1.375 (3) | C221—H22B | 0.98 |
O12—C121 | 1.418 (2) | C221—H22C | 0.98 |
C121—H12A | 0.98 | C23—C24 | 1.400 (3) |
C121—H12B | 0.98 | C23—H23 | 0.95 |
C121—H12C | 0.98 | C24—C25 | 1.368 (3) |
C13—C14 | 1.405 (3) | C24—H24 | 0.95 |
C13—H13 | 0.95 | C25—C26 | 1.417 (3) |
C14—C15 | 1.366 (3) | C25—H25 | 0.95 |
C14—H14 | 0.95 | C26—C27 | 1.438 (3) |
C15—C16 | 1.409 (3) | C27—N27 | 1.291 (2) |
C15—H15 | 0.95 | C27—H27 | 0.95 |
C16—C17 | 1.445 (3) | N27—C28 | 1.474 (2) |
C17—N17 | 1.286 (2) | C28—H28A | 0.98 |
C17—H17 | 0.95 | C28—H28B | 0.98 |
N17—C18 | 1.471 (2) | C28—H28C | 0.98 |
C18—H18A | 0.98 | ||
O21—Ni1—O11 | 175.66 (6) | N17—C18—H18C | 109.5 |
O21—Ni1—N27 | 91.09 (6) | H18A—C18—H18C | 109.5 |
O11—Ni1—N27 | 90.00 (6) | H18B—C18—H18C | 109.5 |
O21—Ni1—N17 | 87.57 (6) | O21—C21—C26 | 124.35 (17) |
O11—Ni1—N17 | 90.70 (6) | O21—C21—C22 | 118.23 (16) |
N27—Ni1—N17 | 170.92 (6) | C26—C21—C22 | 117.40 (17) |
Ni1—O11—Ni1i | 101.44 (2) | C21—O21—Ni1 | 128.01 (12) |
O11—C11—C16 | 123.79 (17) | O22—C22—C23 | 124.36 (18) |
O11—C11—C12 | 118.34 (16) | O22—C22—C21 | 114.39 (16) |
C16—C11—C12 | 117.84 (17) | C23—C22—C21 | 121.25 (17) |
C11—O11—Ni1 | 126.08 (12) | C22—O22—C221 | 116.62 (15) |
O12—C12—C13 | 124.95 (18) | O22—C221—H22A | 109.5 |
O12—C12—C11 | 113.97 (16) | O22—C221—H22B | 109.5 |
C13—C12—C11 | 121.06 (18) | H22A—C221—H22B | 109.5 |
C12—O12—C121 | 116.98 (16) | O22—C221—H22C | 109.5 |
O12—C121—H12A | 109.5 | H22A—C221—H22C | 109.5 |
O12—C121—H12B | 109.5 | H22B—C221—H22C | 109.5 |
H12A—C121—H12B | 109.5 | C22—C23—C24 | 120.45 (19) |
O12—C121—H12C | 109.5 | C22—C23—H23 | 119.8 |
H12A—C121—H12C | 109.5 | C24—C23—H23 | 119.8 |
H12B—C121—H12C | 109.5 | C25—C24—C23 | 119.73 (19) |
C12—C13—C14 | 120.08 (18) | C25—C24—H24 | 120.1 |
C12—C13—H13 | 120 | C23—C24—H24 | 120.1 |
C14—C13—H13 | 120 | C24—C25—C26 | 121.09 (19) |
C15—C14—C13 | 120.23 (18) | C24—C25—H25 | 119.5 |
C15—C14—H14 | 119.9 | C26—C25—H25 | 119.5 |
C13—C14—H14 | 119.9 | C21—C26—C25 | 120.06 (18) |
C14—C15—C16 | 120.59 (19) | C21—C26—C27 | 121.62 (17) |
C14—C15—H15 | 119.7 | C25—C26—C27 | 118.00 (17) |
C16—C15—H15 | 119.7 | N27—C27—C26 | 126.29 (17) |
C15—C16—C11 | 120.18 (18) | N27—C27—H27 | 116.9 |
C15—C16—C17 | 117.99 (17) | C26—C27—H27 | 116.9 |
C11—C16—C17 | 121.82 (16) | C27—N27—C28 | 116.31 (16) |
N17—C17—C16 | 126.25 (17) | C27—N27—Ni1 | 123.84 (13) |
N17—C17—H17 | 116.9 | C28—N27—Ni1 | 119.81 (13) |
C16—C17—H17 | 116.9 | N27—C28—H28A | 109.5 |
C17—N17—C18 | 116.94 (16) | N27—C28—H28B | 109.5 |
C17—N17—Ni1 | 124.21 (13) | H28A—C28—H28B | 109.5 |
C18—N17—Ni1 | 118.85 (12) | N27—C28—H28C | 109.5 |
N17—C18—H18A | 109.5 | H28A—C28—H28C | 109.5 |
N17—C18—H18B | 109.5 | H28B—C28—H28C | 109.5 |
H18A—C18—H18B | 109.5 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C28—H28A···O22ii | 0.98 | 2.57 | 3.449 (2) | 150 |
C28—H28A···O22ii | 0.98 | 2.57 | 3.449 (2) | 150 |
C28—H28C···N17i | 0.98 | 2.63 | 3.432 (3) | 139 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1/2, −y+3/2, −z+1. |
Funding information
Funding for this research was provided by: Ministry of Education and Science of Ukraine (project No. 19BF037-05).
References
Andruh, M. (2015). Dalton Trans. 44, 16633–16653. Web of Science CrossRef CAS PubMed Google Scholar
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Buvaylo, E. A., Kokozay, V. N., Vassilyeva, O. Y., Skelton, B. W., Jezierska, J., Brunel, L. C. & Ozarowski, A. (2005). Chem. Commun. pp. 4976–4978. CSD CrossRef Google Scholar
Buvaylo, E. A., Nesterova, O. V., Kokozay, V. N., Vassilyeva, O. Y., Skelton, B. W., Boča, R. & Nesterov, D. S. (2012). Cryst. Growth Des. 12, 3200–3208. CSD CrossRef CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CrossRef IUCr Journals Google Scholar
Hazra, S., Chakraborty, P. & Mohanta, S. (2016). Cryst. Growth Des. 16, 3777–3790. CSD CrossRef CAS Google Scholar
Kokozay, V. N., Vassilyeva, O. Y. & Makhankova, V. G. (2018). Direct Synthesis of Metal Complexes, edited by B. Kharisov, pp. 183–237. Amsterdam: Elsevier. Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Meally, S. T., McDonald, C., Karotsis, G., Papaefstathiou, G. S., Brechin, E. K., Dunne, P. W., McArdle, P., Power, N. P. & Jones, L. F. (2010). Dalton Trans. 39, 4809–4816. Web of Science CSD CrossRef CAS PubMed Google Scholar
Meally, S. T., McDonald, C., Kealy, P., Taylor, S. M., Brechin, E. K. & Jones, L. F. (2012). Dalton Trans. 41, 5610–5616. Web of Science CSD CrossRef CAS PubMed Google Scholar
Meally, S. T., Taylor, S. M., Brechin, E. K., Piligkos, S. & Jones, L. F. (2013). Dalton Trans. 42, 10315–10325. CSD CrossRef CAS PubMed Google Scholar
Nesterova, O. V., Kasyanova, K. V., Buvaylo, E. A., Vassilyeva, O. Y., Skelton, B. W., Nesterov, D. S. & Pombeiro, A. J. (2019). Catalysts, 9, 209. CrossRef Google Scholar
Nesterova, O. V., Kasyanova, K. V., Makhankova, V. G., Kokozay, V. N., Vassilyeva, O. Y., Skelton, B. W., Nesterov, D. S. & Pombeiro, A. J. L. (2018). Appl. Catal. A Gen. 560, 171–184. CSD CrossRef CAS Google Scholar
Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sydoruk, T. V., Buvaylo, E. A., Kokozay, V. N., Vassilyeva, O. Y. & Skelton, B. W. (2013). Acta Cryst. E69, m551–m552. CSD CrossRef IUCr Journals Google Scholar
Vassilyeva, O. Y., Kasyanova, K. V., Kokozay, V. N. & Skelton, B. W. (2018). Acta Cryst. E74, 1532–1535. CSD CrossRef IUCr Journals Google Scholar
Zhang, S.-H. & Feng, C. (2010). J. Mol. Struct. 977, 62–66. Web of Science CSD CrossRef CAS Google Scholar
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