research communications
3CN)](BF4)2 {bztmpen is N-benzyl-N,N′,N′-tris[(6-methylpyridin-2-yl)methyl]ethane-1,2-diamine}
and electrochemical properties of [Ni(bztmpen)(CHaScience and Technology on Surface Physics and Chemistry Laboratory, Jiangyou 621908, People's Republic of China, and bInstitute of Materials, China Academy of Engineering Physics, Jiangyou 621908, People's Republic of China
*Correspondence e-mail: chenlin101101@aliyun.com
The mononuclear nickel title complex (acetonitrile-κN){N-benzyl-N,N′,N′-tris[(6-methylpyridin-2-yl)methyl]ethane-1,2-diamine}nickel(II) bis(tetrafluoridoborate), [Ni(C30H35N5)(CH3CN)](BF4)2, was prepared from the reaction of Ni(BF4)2·6H2O with N-benzyl-N,N′,N′-tris[(6-methylpyridin-2-yl)methyl]ethane-1,2-diamine (bztmpen) in acetonitrile at room temperature. With an open site occupied by the acetonitrile molecule, the nickel(II) atom is chelated by five N-atom sites from the ligand and one N atom from the ligand, showing an overall octahedral coordination environment. Compared with analogues where the 6–methyl substituent is absent, the bond length around the Ni2+ cation are evidently longer. Upon reductive dissociation of the acetronitrile molecule, the title complex has an open site for a catalytic reaction. The title complex has two redox couples at −1.50 and −1.80 V (versus Fc+/0) based on nickel. The F atoms of the two BF4− counter-anions are split into two groups and the occupancy ratios refined to 0.611 (18):0.389 (18) and 0.71 (2):0.29 (2).
Keywords: crystal structure; nickel; poly-pyridine-diamine; electro-catalyst.
CCDC reference: 1548052
1. Chemical context
Nickel complexes with polypyridine–amine ligands are of great interest in catalytic reactions. For example, nickel complexes containing N5-pentadentate ligands with different amine-to-pyridine ratios have been studied for electrochemical H2 production in water at pH = 7 and the complex with a diamine–tripyridine ligand displays a TON (turn-over number) of up to 308000 over 60 h electrolysis at −1.25 V vs the (SHE), with a Faradaic efficiency of 91% (Zhang et al., 2014). The nickel-based complex Ni–PY5 {PY5 = 2,6-bis[1,1-bis(2-pyridyl)ethyl]pyridine} has been found to act as an electro-catalyst for oxidizing water to dioxygen in aqueous phosphate buffer solutions (Wang et al., 2016). The rate of water oxidation catalyzed by the Ni–PY5 complex is enhanced remarkably by the proton-acceptor base HPO42−, with a of 1820 M−1 s−1. A stable configuration is important for the stability of a catalyst. In the title complex, the Ni2+ cation is chelated by five N-atom sites, so the configuration is stable. With the reductive dissociation of acetonitrile, the title complex would give an open site for a catalytic reaction. Herein, we describe the and electrochemical properties of the title complex.
2. Structural commentary
In the title complex (Fig. 1), the coordination sphere of the nickel(II) atom adopts a normal octahedral geometry. The Ni2+ cation lies almost in the equatorial plane. One pyridine nitrogen atom (N1) and two amino nitrogen atoms (N2, N3) as well as the nitrogen atom of an acetonitrile ligand (N4) form the equatorial plane. The latter can easily be dissociated from nickel. The axial positions are occupied by two pyridine nitrogen atoms (N5, N6). The Ni—N bond lengths for the two axial pyridine–nitrogen atoms [Ni—N5 = 2.209 (3) and Ni—N6 = 2.187 (3) Å] are significantly longer than that for the other four nitrogen atoms [Ni—N1 = 2.151 (3), Ni—N2 = 2.082 (3), Ni—N3 = 2.188 (2), Ni—N4 = 2.061 (3) Å]. The presence of the 6-methyl substituent hinders the approach of the pyridine group to the Ni2+ core. A a result of the from the methyl substituent, the three atoms N5, Ni1 and N6 are not completely linear in the axial direction, with a contact angle of 170.89 (9)°. Two intramolecular C—H⋯N contacts occur (Table 1).
3. Electrochemical commentary
Generally, the reduction of a metal complex is accompanied by the dissociation of the ligand, or the weakest ligand if more than one ligand is present, which could induce the appearance of an open site for a catalytic reaction (Knoll et al., 2014; Johnson et al., 2016). The introduction of o-methyl in the title complex is in favor of the dissociation of acetonitrile. On the cathodic scan under Ar, the title complex features one reversible couple at −1.50 V and one half-reversible couple at −1.80 V (vs Fc+/0) based on nickel, assigned to NiII/I and NiI/0 respectively (Fig. 2). The third couple at −2.15 V could be assigned to the reduction of pyridine. The free ligand bztmpen itself is electrochemically silent in the potential range (Fig. 3). The coordination with nickel leads to a positive shift of the reduction on pyridine. The good reversibility of the couple indicates a negligible change in the configuration of the title complex after one electron reduction. The second reduction might result in a change of the configuration. Analogues in the absence of o-methyl show only one redox couple more negative than −1.50 V (vs Fc+/0; Zhang et al., 2014). The positive shift of the first redox couple for the title complex results from the weaker electron-donating ability of the pyridine ligands, which are farther from the nickel core. The electrochemical properties of these analogues are consistent with the differences shown in the structure.
4. Supramolecular features
In the title crystal, no classical hydrogen bonds have been found. Weak C—H⋯F contacts (Table 1) link the components into a three-dimensional network. The crytal paacking is illustrated in Fig. 4.
5. Database survey
There are three published nickel complexes with poly-pyridine groups (Shi et al., 2015; Zhang et al., 2014; Wang et al., 2016), but to the best of our knowledge, the title compound has not been reported previously. The nickel complex with N,N,N′,N′-tetra(2-pyridylmethyl)ethylenediamine (tpen) adopts a normal octahedral geometry (Shi et al., 2015). In the Ni2+(tpen) complex, the Ni—N1, Ni—N2, Ni—N3, Ni—N4, Ni—N5 and Ni—N6 bonds [2.106 (3), 2.099 (3), 2.114 (3), 2.086 (3), 2.094 (3) and 2.120 (2) Å, respectively] are shorter than the corresponding bond lengths in the title complex. Among the earliest reports, the nickel complex with N-benzyl-N,N′,N′-tris(2-pyridylmethyl)ethylenediamine (bztpen) ligand is most similar to the title complex (Zhang et al., 2014). Under reductive conditions, Ni2+(bztpen) displays a high activity on electro-catalytic water reduction. The title complex possesses a higher than Ni2+(bztpen), which affects evidently the bond lengths, especially in the axial direction. The bonds lengths in the title complex [Ni—N5 = 2.209 (3), Ni—N6 = 2.187 (3) Å] are longer than those in Ni2+(bztpen) [Ni—N5 = 2.149 (3), Ni—N6 = 2.096 (3) Å]. The nickel complex with a PY5 ligand {PY5 = 2,6-bis[1,1-bis(2-pyridyl)ethyl]pyridine} displays a similar configuration to the title complex, but the labile ligand is at the axial site (Wang et al., 2016). Ni2+(PY5) has been found to act as an electro-catalyst for oxidizing water to dioxygen in an aqueous phosphate buffer solution.
6. Synthesis and crystallization
The tripyridine-diamine ligand N-benzyl-N,N′,N′-tris[(6-methylpyridin-2-yl)methyl]ethane-1,2-diamine (bztmpen) was prepared according to literature procedures (Zhang et al., 2013), 1H NMR (CDCl3, 600 MHz): δ 7.44 (m, 4H), 7.25 (m, 6H), 6.96 (m, 4H), 3.74 (s, 6H), 3.58 (s, 2H), 2.75 (d, 4H), 2.49 (s, 9H). ESI–MS: calculated for [M + H]+: m/z 466.63; found: 466.27.
Preparation of [Ni(bztmpen)(CH3CN)](BF4)2. Compound Ni(BF4)2·6H2O (0.16 g, 0.5 mmol) was added to an acetonitrile solution (5 mL) of bztmpen (0.2 g, 0.5 mmol). The mixture was stirred at room temperature for 6 h. The purple solution was then transferred to tubes, which were placed in a flask containing ether. Block-shaped blue crystals were obtained in a yield of 85% (0.25 g). Analysis calculated for C32H38B2F8N6Ni (%): C, 50.01; H, 5.18; N, 11.37; found: 50.01; H, 5.19; N, 11.36; MS (TOF–ES): m/z = 282.6341 {[M−2BF4−]/2}+, 599.3015 [M – 2BF4− + Cl−]+.
7. Refinement
Crystal data, data collection and structure . The F atoms of the two BF4− counter-anions were split into two groups and the occupancies refined to 0.611 (18)/0.389 (18) and 0.71 (2)/0.29 (2). The hydrogen atoms were refined in a riding mode with C—H = 0.93–0.97 Å and Uiso(H) = 1.2Ueq(C).
details are summarized in Table 2
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Supporting information
CCDC reference: 1548052
https://doi.org/10.1107/S2056989017006764/vn2128sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017006764/vn2128Isup4.hkl
Data collection: SMART (Bruker, 2016); cell
SMART (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).[Ni(C30H35N5)(C2H3N)](BF4)2 | F(000) = 1528 |
Mr = 739.01 | Dx = 1.441 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
a = 11.230 (3) Å | Cell parameters from 8509 reflections |
b = 17.204 (5) Å | θ = 2.3–28.4° |
c = 18.110 (6) Å | µ = 0.65 mm−1 |
β = 103.248 (7)° | T = 298 K |
V = 3405.7 (18) Å3 | Block, blue |
Z = 4 | 0.30 × 0.20 × 0.10 mm |
Bruker SMART CCD area detector diffractometer | 6304 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.032 |
phi and ω scans | θmax = 28.4°, θmin = 3.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −14→11 |
Tmin = 0.847, Tmax = 0.955 | k = −22→22 |
14710 measured reflections | l = −24→24 |
6476 independent reflections |
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.060P)2 + 1.7104P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.035 | (Δ/σ)max = 0.001 |
wR(F2) = 0.092 | Δρmax = 0.29 e Å−3 |
S = 1.03 | Δρmin = −0.25 e Å−3 |
6476 reflections | Extinction correction: SHELXL2016 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
520 parameters | Extinction coefficient: 0.0091 (17) |
2 restraints | Absolute structure: Classical Flack method preferred over Parsons because s.u. lower. |
Hydrogen site location: mixed | Absolute structure parameter: −0.017 (12) |
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 | Occ. (<1) | |
Ni1 | 0.73459 (2) | −0.19011 (2) | 0.24468 (2) | 0.02752 (12) | |
N1 | 0.6542 (3) | −0.29110 (15) | 0.18272 (14) | 0.0333 (5) | |
N2 | 0.5812 (3) | −0.20749 (17) | 0.28899 (14) | 0.0331 (5) | |
N3 | 0.7742 (3) | −0.09858 (14) | 0.33073 (13) | 0.0325 (5) | |
N4 | 0.8969 (3) | −0.17465 (19) | 0.21169 (18) | 0.0395 (6) | |
N5 | 0.8531 (3) | −0.25827 (15) | 0.33616 (14) | 0.0361 (5) | |
N6 | 0.6119 (2) | −0.11087 (13) | 0.16863 (13) | 0.0303 (5) | |
C1 | 0.7455 (4) | −0.2798 (2) | 0.0724 (2) | 0.0515 (9) | |
H1A | 0.727964 | −0.299078 | 0.021314 | 0.077* | |
H1B | 0.830687 | −0.287160 | 0.095248 | 0.077* | |
H1C | 0.726121 | −0.225425 | 0.072011 | 0.077* | |
C2 | 0.6698 (3) | −0.32319 (17) | 0.11726 (17) | 0.0354 (6) | |
C3 | 0.6181 (4) | −0.3937 (2) | 0.0906 (2) | 0.0460 (8) | |
H3A | 0.631892 | −0.414716 | 0.045975 | 0.055* | |
C4 | 0.5459 (4) | −0.4324 (2) | 0.1306 (3) | 0.0599 (10) | |
H4A | 0.510311 | −0.479825 | 0.113295 | 0.072* | |
C5 | 0.5270 (5) | −0.3999 (2) | 0.1971 (3) | 0.0569 (10) | |
H5A | 0.478334 | −0.425011 | 0.224961 | 0.068* | |
C6 | 0.5816 (3) | −0.32968 (18) | 0.22115 (19) | 0.0382 (6) | |
C7 | 0.5658 (4) | −0.29254 (19) | 0.29387 (19) | 0.0421 (7) | |
H7A | 0.485006 | −0.304199 | 0.301634 | 0.051* | |
H7B | 0.626011 | −0.313171 | 0.336524 | 0.051* | |
C8 | 0.6011 (3) | −0.1684 (2) | 0.36392 (17) | 0.0405 (7) | |
H8A | 0.653812 | −0.200003 | 0.402342 | 0.049* | |
H8B | 0.523544 | −0.161637 | 0.378152 | 0.049* | |
C9 | 0.6601 (3) | −0.08985 (19) | 0.35846 (17) | 0.0379 (6) | |
H9A | 0.603190 | −0.056630 | 0.324016 | 0.046* | |
H9B | 0.678916 | −0.065285 | 0.407993 | 0.046* | |
C10 | 0.8122 (4) | −0.02283 (16) | 0.30210 (16) | 0.0376 (6) | |
H10A | 0.747853 | −0.006513 | 0.259492 | 0.045* | |
H10B | 0.884650 | −0.032304 | 0.282792 | 0.045* | |
C11 | 0.8397 (3) | 0.04463 (17) | 0.35776 (17) | 0.0387 (6) | |
C12 | 0.9533 (4) | 0.0523 (2) | 0.4080 (2) | 0.0506 (8) | |
H12A | 1.011855 | 0.013546 | 0.410691 | 0.061* | |
C13 | 0.9795 (5) | 0.1177 (3) | 0.4540 (2) | 0.0639 (12) | |
H13A | 1.055817 | 0.122176 | 0.487139 | 0.077* | |
C14 | 0.8960 (6) | 0.1749 (3) | 0.4515 (3) | 0.0665 (15) | |
H14A | 0.915001 | 0.218324 | 0.482537 | 0.080* | |
C15 | 0.7850 (7) | 0.1685 (3) | 0.4038 (4) | 0.0741 (17) | |
H15A | 0.727325 | 0.207599 | 0.402322 | 0.089* | |
C16 | 0.7555 (5) | 0.1034 (2) | 0.3562 (3) | 0.0588 (10) | |
H16A | 0.678691 | 0.099906 | 0.323433 | 0.071* | |
C17 | 0.8769 (5) | −0.3819 (2) | 0.2717 (2) | 0.0618 (11) | |
H17A | 0.947332 | −0.415222 | 0.279414 | 0.093* | |
H17B | 0.877006 | −0.347513 | 0.229995 | 0.093* | |
H17C | 0.803989 | −0.412999 | 0.260617 | 0.093* | |
C18 | 0.8809 (4) | −0.3350 (2) | 0.3424 (2) | 0.0462 (7) | |
C19 | 0.9179 (5) | −0.3706 (2) | 0.4121 (3) | 0.0648 (12) | |
H19A | 0.935934 | −0.423435 | 0.414915 | 0.078* | |
C20 | 0.9283 (6) | −0.3275 (3) | 0.4778 (3) | 0.0703 (14) | |
H20A | 0.946599 | −0.351625 | 0.525012 | 0.084* | |
C21 | 0.9112 (4) | −0.2481 (2) | 0.4721 (2) | 0.0530 (9) | |
H21A | 0.923136 | −0.217195 | 0.515292 | 0.064* | |
C22 | 0.8758 (3) | −0.21540 (18) | 0.40064 (17) | 0.0374 (6) | |
C23 | 0.8742 (3) | −0.12851 (18) | 0.39211 (17) | 0.0391 (6) | |
H23A | 0.866918 | −0.105272 | 0.439683 | 0.047* | |
H23B | 0.951744 | −0.111991 | 0.382379 | 0.047* | |
C24 | 0.4730 (3) | −0.1755 (2) | 0.23570 (19) | 0.0376 (6) | |
H24A | 0.416027 | −0.156355 | 0.264446 | 0.045* | |
H24B | 0.432739 | −0.217051 | 0.203176 | 0.045* | |
C25 | 0.5017 (3) | −0.11045 (16) | 0.18656 (15) | 0.0328 (5) | |
C26 | 0.4120 (4) | −0.0560 (2) | 0.1587 (2) | 0.0485 (8) | |
H26A | 0.338511 | −0.056083 | 0.174092 | 0.058* | |
C27 | 0.4340 (4) | −0.0012 (2) | 0.1072 (3) | 0.0581 (10) | |
H27A | 0.374968 | 0.035766 | 0.087176 | 0.070* | |
C28 | 0.5429 (4) | −0.00225 (18) | 0.0866 (2) | 0.0481 (8) | |
H28A | 0.557883 | 0.033626 | 0.051338 | 0.058* | |
C29 | 0.6327 (3) | −0.05676 (16) | 0.11773 (16) | 0.0356 (6) | |
C30 | 0.7518 (4) | −0.0552 (2) | 0.0947 (2) | 0.0522 (9) | |
H30A | 0.749443 | −0.015746 | 0.056818 | 0.078* | |
H30B | 0.766266 | −0.104850 | 0.074227 | 0.078* | |
H30C | 0.816492 | −0.043836 | 0.138065 | 0.078* | |
C31 | 0.9942 (4) | −0.1705 (3) | 0.2068 (2) | 0.0524 (9) | |
C32 | 1.1190 (6) | −0.1620 (6) | 0.1991 (5) | 0.116 (3) | |
H32A | 1.151132 | −0.112648 | 0.219080 | 0.139* | |
H32B | 1.121102 | −0.165218 | 0.146450 | 0.139* | |
H32C | 1.167603 | −0.203008 | 0.226670 | 0.139* | |
B1 | −0.2984 (7) | 0.1828 (4) | 0.0952 (4) | 0.0668 (16) | |
B2 | 0.2397 (7) | −0.0699 (4) | 0.3807 (4) | 0.0734 (15) | |
F1 | −0.2730 (12) | 0.1428 (8) | 0.1633 (4) | 0.118 (4) | 0.71 (2) |
F2 | −0.4166 (9) | 0.1922 (5) | 0.0757 (8) | 0.124 (5) | 0.71 (2) |
F3 | −0.2264 (10) | 0.2458 (7) | 0.1037 (7) | 0.111 (4) | 0.71 (2) |
F4 | −0.275 (2) | 0.1337 (9) | 0.0395 (8) | 0.093 (5) | 0.71 (2) |
F1A | −0.233 (2) | 0.181 (2) | 0.1638 (17) | 0.138 (11) | 0.29 (2) |
F2A | −0.411 (3) | 0.185 (2) | 0.111 (3) | 0.21 (2) | 0.29 (2) |
F3A | −0.287 (4) | 0.2622 (10) | 0.067 (2) | 0.127 (12) | 0.29 (2) |
F4A | −0.251 (6) | 0.1297 (18) | 0.054 (2) | 0.098 (10) | 0.29 (2) |
F5 | 0.205 (2) | −0.1435 (7) | 0.3810 (10) | 0.208 (10) | 0.611 (18) |
F6 | 0.1540 (9) | −0.0300 (7) | 0.3264 (5) | 0.122 (4) | 0.611 (18) |
F7 | 0.3403 (11) | −0.0688 (7) | 0.3563 (10) | 0.135 (5) | 0.611 (18) |
F8 | 0.2472 (17) | −0.0380 (11) | 0.4477 (6) | 0.137 (6) | 0.611 (18) |
F5A | 0.348 (2) | −0.105 (3) | 0.414 (4) | 0.30 (2) | 0.389 (18) |
F6A | 0.1583 (13) | −0.1213 (13) | 0.3817 (13) | 0.125 (8) | 0.389 (18) |
F7A | 0.246 (7) | −0.0368 (13) | 0.3222 (13) | 0.30 (3) | 0.389 (18) |
F8A | 0.2379 (16) | −0.0186 (17) | 0.4387 (13) | 0.126 (8) | 0.389 (18) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.02251 (17) | 0.03240 (16) | 0.02857 (16) | −0.00093 (15) | 0.00773 (11) | 0.00228 (14) |
N1 | 0.0299 (13) | 0.0365 (11) | 0.0343 (11) | −0.0040 (11) | 0.0090 (10) | 0.0032 (9) |
N2 | 0.0284 (14) | 0.0418 (11) | 0.0315 (11) | −0.0022 (12) | 0.0119 (10) | 0.0037 (10) |
N3 | 0.0326 (14) | 0.0335 (10) | 0.0312 (10) | 0.0008 (10) | 0.0068 (10) | 0.0013 (9) |
N4 | 0.0288 (15) | 0.0488 (13) | 0.0434 (14) | −0.0049 (13) | 0.0132 (12) | −0.0014 (12) |
N5 | 0.0320 (13) | 0.0372 (12) | 0.0362 (11) | 0.0008 (11) | 0.0021 (10) | 0.0009 (10) |
N6 | 0.0281 (12) | 0.0332 (10) | 0.0294 (10) | −0.0016 (9) | 0.0065 (9) | 0.0017 (8) |
C1 | 0.066 (3) | 0.0537 (18) | 0.0417 (15) | −0.0160 (18) | 0.0256 (17) | −0.0068 (14) |
C2 | 0.0337 (16) | 0.0370 (12) | 0.0347 (13) | −0.0021 (12) | 0.0060 (12) | 0.0009 (11) |
C3 | 0.044 (2) | 0.0420 (15) | 0.0517 (18) | −0.0067 (15) | 0.0094 (16) | −0.0100 (14) |
C4 | 0.056 (3) | 0.0379 (16) | 0.088 (3) | −0.0169 (17) | 0.022 (2) | −0.0129 (17) |
C5 | 0.059 (3) | 0.0411 (16) | 0.078 (3) | −0.0205 (17) | 0.031 (2) | −0.0019 (17) |
C6 | 0.0331 (16) | 0.0349 (13) | 0.0491 (16) | −0.0040 (12) | 0.0147 (13) | 0.0065 (12) |
C7 | 0.0426 (19) | 0.0430 (14) | 0.0469 (16) | −0.0064 (14) | 0.0229 (15) | 0.0086 (13) |
C8 | 0.0397 (17) | 0.0529 (16) | 0.0331 (13) | −0.0016 (15) | 0.0171 (13) | 0.0012 (12) |
C9 | 0.0375 (16) | 0.0451 (14) | 0.0323 (12) | 0.0035 (13) | 0.0104 (12) | −0.0047 (11) |
C10 | 0.0492 (19) | 0.0302 (12) | 0.0334 (12) | −0.0008 (12) | 0.0092 (12) | 0.0013 (10) |
C11 | 0.0458 (19) | 0.0350 (12) | 0.0376 (13) | −0.0027 (13) | 0.0143 (13) | −0.0011 (11) |
C12 | 0.055 (2) | 0.0464 (17) | 0.0496 (17) | −0.0074 (17) | 0.0103 (17) | −0.0017 (14) |
C13 | 0.076 (3) | 0.069 (2) | 0.0478 (18) | −0.029 (2) | 0.016 (2) | −0.0131 (17) |
C14 | 0.093 (4) | 0.057 (2) | 0.060 (2) | −0.020 (2) | 0.038 (3) | −0.0246 (19) |
C15 | 0.088 (5) | 0.053 (2) | 0.091 (4) | 0.008 (3) | 0.041 (4) | −0.021 (3) |
C16 | 0.059 (3) | 0.0444 (17) | 0.074 (2) | 0.0061 (18) | 0.016 (2) | −0.0109 (17) |
C17 | 0.067 (3) | 0.0478 (19) | 0.062 (2) | 0.025 (2) | −0.003 (2) | −0.0082 (16) |
C18 | 0.0418 (19) | 0.0396 (14) | 0.0519 (18) | 0.0044 (15) | −0.0004 (15) | −0.0004 (14) |
C19 | 0.077 (3) | 0.0410 (18) | 0.065 (2) | 0.011 (2) | −0.006 (2) | 0.0104 (17) |
C20 | 0.094 (4) | 0.057 (2) | 0.048 (2) | 0.011 (3) | −0.008 (2) | 0.0191 (17) |
C21 | 0.062 (3) | 0.0508 (18) | 0.0377 (15) | 0.0027 (18) | −0.0049 (16) | 0.0066 (13) |
C22 | 0.0342 (16) | 0.0367 (13) | 0.0366 (13) | 0.0000 (13) | −0.0017 (12) | 0.0033 (11) |
C23 | 0.0385 (17) | 0.0373 (13) | 0.0358 (13) | −0.0018 (13) | −0.0031 (12) | −0.0006 (11) |
C24 | 0.0218 (14) | 0.0504 (15) | 0.0420 (15) | −0.0030 (12) | 0.0104 (12) | 0.0007 (12) |
C25 | 0.0257 (14) | 0.0377 (13) | 0.0330 (12) | 0.0018 (11) | 0.0025 (10) | −0.0031 (10) |
C26 | 0.0308 (17) | 0.0517 (17) | 0.0593 (19) | 0.0097 (15) | 0.0027 (15) | 0.0021 (15) |
C27 | 0.048 (2) | 0.0453 (17) | 0.071 (2) | 0.0153 (17) | −0.0058 (18) | 0.0078 (16) |
C28 | 0.060 (2) | 0.0326 (13) | 0.0449 (16) | 0.0005 (15) | −0.0022 (16) | 0.0093 (12) |
C29 | 0.0428 (18) | 0.0313 (12) | 0.0300 (11) | −0.0028 (12) | 0.0030 (12) | 0.0020 (10) |
C30 | 0.055 (2) | 0.0528 (18) | 0.0553 (19) | −0.0033 (17) | 0.0252 (18) | 0.0177 (16) |
C31 | 0.038 (2) | 0.066 (2) | 0.059 (2) | −0.0107 (18) | 0.0219 (17) | −0.0207 (18) |
C32 | 0.047 (3) | 0.176 (7) | 0.139 (6) | −0.035 (4) | 0.050 (4) | −0.083 (6) |
B1 | 0.062 (4) | 0.071 (3) | 0.062 (3) | −0.015 (3) | 0.004 (3) | −0.014 (2) |
B2 | 0.081 (4) | 0.073 (3) | 0.072 (3) | 0.004 (3) | 0.029 (3) | 0.004 (3) |
F1 | 0.127 (8) | 0.174 (9) | 0.049 (3) | 0.013 (6) | 0.014 (3) | 0.000 (4) |
F2 | 0.066 (5) | 0.090 (5) | 0.181 (10) | 0.003 (4) | −0.044 (6) | −0.009 (5) |
F3 | 0.106 (6) | 0.105 (6) | 0.136 (7) | −0.057 (5) | 0.055 (5) | −0.073 (6) |
F4 | 0.157 (13) | 0.077 (5) | 0.052 (3) | −0.032 (6) | 0.036 (6) | −0.014 (3) |
F1A | 0.069 (12) | 0.17 (3) | 0.15 (2) | 0.006 (12) | −0.033 (12) | −0.037 (17) |
F2A | 0.14 (2) | 0.20 (3) | 0.34 (5) | −0.10 (2) | 0.18 (3) | −0.16 (3) |
F3A | 0.20 (3) | 0.060 (6) | 0.17 (2) | 0.013 (11) | 0.14 (2) | 0.025 (10) |
F4A | 0.135 (19) | 0.047 (8) | 0.11 (2) | −0.006 (9) | 0.017 (18) | −0.020 (10) |
F5 | 0.35 (3) | 0.080 (6) | 0.159 (11) | −0.074 (10) | −0.018 (14) | 0.039 (6) |
F6 | 0.125 (7) | 0.170 (9) | 0.071 (4) | 0.085 (7) | 0.020 (4) | 0.029 (4) |
F7 | 0.098 (7) | 0.134 (8) | 0.207 (13) | 0.026 (5) | 0.105 (9) | −0.001 (7) |
F8 | 0.174 (13) | 0.183 (13) | 0.053 (4) | −0.015 (9) | 0.025 (5) | 0.006 (6) |
F5A | 0.087 (14) | 0.37 (5) | 0.44 (6) | 0.09 (2) | 0.06 (3) | −0.03 (5) |
F6A | 0.056 (6) | 0.179 (19) | 0.151 (13) | −0.046 (8) | 0.047 (8) | −0.033 (12) |
F7A | 0.73 (8) | 0.102 (13) | 0.113 (13) | −0.14 (3) | 0.18 (3) | −0.021 (10) |
F8A | 0.061 (7) | 0.163 (15) | 0.155 (17) | −0.008 (8) | 0.029 (9) | −0.090 (13) |
Ni1—N4 | 2.061 (3) | C15—H15A | 0.9300 |
Ni1—N2 | 2.082 (3) | C16—H16A | 0.9300 |
Ni1—N1 | 2.151 (3) | C17—C18 | 1.505 (5) |
Ni1—N6 | 2.187 (3) | C17—H17A | 0.9600 |
Ni1—N3 | 2.188 (2) | C17—H17B | 0.9600 |
Ni1—N5 | 2.209 (3) | C17—H17C | 0.9600 |
N1—C2 | 1.355 (4) | C18—C19 | 1.378 (6) |
N1—C6 | 1.361 (4) | C19—C20 | 1.385 (7) |
N2—C24 | 1.475 (5) | C19—H19A | 0.9300 |
N2—C7 | 1.479 (4) | C20—C21 | 1.381 (6) |
N2—C8 | 1.485 (4) | C20—H20A | 0.9300 |
N3—C23 | 1.480 (4) | C21—C22 | 1.382 (4) |
N3—C9 | 1.488 (4) | C21—H21A | 0.9300 |
N3—C10 | 1.500 (4) | C22—C23 | 1.503 (4) |
N4—C31 | 1.119 (5) | C23—H23A | 0.9700 |
N5—C22 | 1.355 (4) | C23—H23B | 0.9700 |
N5—C18 | 1.356 (4) | C24—C25 | 1.509 (4) |
N6—C25 | 1.350 (4) | C24—H24A | 0.9700 |
N6—C29 | 1.367 (3) | C24—H24B | 0.9700 |
C1—C2 | 1.502 (4) | C25—C26 | 1.384 (5) |
C1—H1A | 0.9600 | C26—C27 | 1.386 (6) |
C1—H1B | 0.9600 | C26—H26A | 0.9300 |
C1—H1C | 0.9600 | C27—C28 | 1.360 (7) |
C2—C3 | 1.383 (4) | C27—H27A | 0.9300 |
C3—C4 | 1.377 (5) | C28—C29 | 1.398 (5) |
C3—H3A | 0.9300 | C28—H28A | 0.9300 |
C4—C5 | 1.388 (6) | C29—C30 | 1.490 (5) |
C4—H4A | 0.9300 | C30—H30A | 0.9600 |
C5—C6 | 1.380 (5) | C30—H30B | 0.9600 |
C5—H5A | 0.9300 | C30—H30C | 0.9600 |
C6—C7 | 1.510 (4) | C31—C32 | 1.448 (6) |
C7—H7A | 0.9700 | C32—H32A | 0.9600 |
C7—H7B | 0.9700 | C32—H32B | 0.9600 |
C8—C9 | 1.519 (5) | C32—H32C | 0.9598 |
C8—H8A | 0.9700 | B1—F1A | 1.29 (3) |
C8—H8B | 0.9700 | B1—F2 | 1.303 (12) |
C9—H9A | 0.9700 | B1—F3 | 1.339 (10) |
C9—H9B | 0.9700 | B1—F4A | 1.36 (4) |
C10—C11 | 1.522 (4) | B1—F2A | 1.36 (2) |
C10—H10A | 0.9700 | B1—F1 | 1.384 (11) |
C10—H10B | 0.9700 | B1—F4 | 1.385 (14) |
C11—C16 | 1.380 (5) | B1—F3A | 1.470 (16) |
C11—C12 | 1.392 (6) | B2—F7A | 1.219 (16) |
C12—C13 | 1.391 (5) | B2—F6A | 1.276 (17) |
C12—H12A | 0.9300 | B2—F7 | 1.305 (10) |
C13—C14 | 1.352 (8) | B2—F8 | 1.317 (14) |
C13—H13A | 0.9300 | B2—F5 | 1.324 (12) |
C14—C15 | 1.349 (9) | B2—F5A | 1.36 (3) |
C14—H14A | 0.9300 | B2—F8A | 1.38 (2) |
C15—C16 | 1.405 (7) | B2—F6 | 1.389 (10) |
N4—Ni1—N2 | 174.24 (13) | C13—C14—H14A | 120.2 |
N4—Ni1—N1 | 104.24 (12) | C14—C15—C16 | 120.7 (5) |
N2—Ni1—N1 | 78.45 (10) | C14—C15—H15A | 119.6 |
N4—Ni1—N6 | 102.02 (11) | C16—C15—H15A | 119.6 |
N2—Ni1—N6 | 82.81 (10) | C11—C16—C15 | 120.5 (5) |
N1—Ni1—N6 | 92.67 (10) | C11—C16—H16A | 119.8 |
N4—Ni1—N3 | 93.70 (11) | C15—C16—H16A | 119.8 |
N2—Ni1—N3 | 83.11 (10) | C18—C17—H17A | 109.5 |
N1—Ni1—N3 | 160.94 (9) | C18—C17—H17B | 109.5 |
N6—Ni1—N3 | 89.77 (9) | H17A—C17—H17B | 109.5 |
N4—Ni1—N5 | 82.24 (12) | C18—C17—H17C | 109.5 |
N2—Ni1—N5 | 92.54 (11) | H17A—C17—H17C | 109.5 |
N1—Ni1—N5 | 94.07 (11) | H17B—C17—H17C | 109.5 |
N6—Ni1—N5 | 170.89 (9) | N5—C18—C19 | 121.6 (3) |
N3—Ni1—N5 | 81.87 (10) | N5—C18—C17 | 119.3 (3) |
C2—N1—C6 | 117.5 (3) | C19—C18—C17 | 119.0 (4) |
C2—N1—Ni1 | 131.5 (2) | C18—C19—C20 | 119.8 (4) |
C6—N1—Ni1 | 110.9 (2) | C18—C19—H19A | 120.1 |
C24—N2—C7 | 108.6 (3) | C20—C19—H19A | 120.1 |
C24—N2—C8 | 111.0 (3) | C21—C20—C19 | 118.8 (4) |
C7—N2—C8 | 112.9 (2) | C21—C20—H20A | 120.6 |
C24—N2—Ni1 | 108.95 (18) | C19—C20—H20A | 120.6 |
C7—N2—Ni1 | 106.5 (2) | C20—C21—C22 | 118.6 (4) |
C8—N2—Ni1 | 108.8 (2) | C20—C21—H21A | 120.7 |
C23—N3—C9 | 110.2 (2) | C22—C21—H21A | 120.7 |
C23—N3—C10 | 109.6 (3) | N5—C22—C21 | 122.8 (3) |
C9—N3—C10 | 111.4 (2) | N5—C22—C23 | 117.2 (3) |
C23—N3—Ni1 | 106.27 (18) | C21—C22—C23 | 119.7 (3) |
C9—N3—Ni1 | 105.24 (19) | N3—C23—C22 | 114.4 (3) |
C10—N3—Ni1 | 113.98 (16) | N3—C23—H23A | 108.7 |
C31—N4—Ni1 | 167.3 (4) | C22—C23—H23A | 108.7 |
C22—N5—C18 | 117.7 (3) | N3—C23—H23B | 108.7 |
C22—N5—Ni1 | 108.6 (2) | C22—C23—H23B | 108.7 |
C18—N5—Ni1 | 131.8 (2) | H23A—C23—H23B | 107.6 |
C25—N6—C29 | 117.8 (3) | N2—C24—C25 | 114.0 (3) |
C25—N6—Ni1 | 109.39 (18) | N2—C24—H24A | 108.7 |
C29—N6—Ni1 | 131.9 (2) | C25—C24—H24A | 108.7 |
C2—C1—H1A | 109.5 | N2—C24—H24B | 108.7 |
C2—C1—H1B | 109.5 | C25—C24—H24B | 108.7 |
H1A—C1—H1B | 109.5 | H24A—C24—H24B | 107.6 |
C2—C1—H1C | 109.5 | N6—C25—C26 | 123.1 (3) |
H1A—C1—H1C | 109.5 | N6—C25—C24 | 118.0 (3) |
H1B—C1—H1C | 109.5 | C26—C25—C24 | 118.8 (3) |
N1—C2—C3 | 122.3 (3) | C25—C26—C27 | 118.6 (4) |
N1—C2—C1 | 118.2 (3) | C25—C26—H26A | 120.7 |
C3—C2—C1 | 119.4 (3) | C27—C26—H26A | 120.7 |
C4—C3—C2 | 119.4 (3) | C28—C27—C26 | 119.1 (3) |
C4—C3—H3A | 120.3 | C28—C27—H27A | 120.5 |
C2—C3—H3A | 120.3 | C26—C27—H27A | 120.5 |
C3—C4—C5 | 119.2 (3) | C27—C28—C29 | 120.6 (3) |
C3—C4—H4A | 120.4 | C27—C28—H28A | 119.7 |
C5—C4—H4A | 120.4 | C29—C28—H28A | 119.7 |
C6—C5—C4 | 118.8 (3) | N6—C29—C28 | 120.7 (3) |
C6—C5—H5A | 120.6 | N6—C29—C30 | 120.3 (3) |
C4—C5—H5A | 120.6 | C28—C29—C30 | 119.0 (3) |
N1—C6—C5 | 122.8 (3) | C29—C30—H30A | 109.5 |
N1—C6—C7 | 116.3 (3) | C29—C30—H30B | 109.5 |
C5—C6—C7 | 120.9 (3) | H30A—C30—H30B | 109.5 |
N2—C7—C6 | 109.1 (2) | C29—C30—H30C | 109.5 |
N2—C7—H7A | 109.9 | H30A—C30—H30C | 109.5 |
C6—C7—H7A | 109.9 | H30B—C30—H30C | 109.5 |
N2—C7—H7B | 109.9 | N4—C31—C32 | 177.5 (7) |
C6—C7—H7B | 109.9 | C31—C32—H32A | 110.0 |
H7A—C7—H7B | 108.3 | C31—C32—H32B | 109.6 |
N2—C8—C9 | 108.6 (2) | H32A—C32—H32B | 109.5 |
N2—C8—H8A | 110.0 | C31—C32—H32C | 108.8 |
C9—C8—H8A | 110.0 | H32A—C32—H32C | 109.5 |
N2—C8—H8B | 110.0 | H32B—C32—H32C | 109.5 |
C9—C8—H8B | 110.0 | F2—B1—F3 | 118.9 (9) |
H8A—C8—H8B | 108.3 | F1A—B1—F4A | 107 (3) |
N3—C9—C8 | 110.8 (2) | F1A—B1—F2A | 99 (2) |
N3—C9—H9A | 109.5 | F4A—B1—F2A | 129 (3) |
C8—C9—H9A | 109.5 | F2—B1—F1 | 107.0 (9) |
N3—C9—H9B | 109.5 | F3—B1—F1 | 107.7 (8) |
C8—C9—H9B | 109.5 | F2—B1—F4 | 103.1 (13) |
H9A—C9—H9B | 108.1 | F3—B1—F4 | 111.7 (10) |
N3—C10—C11 | 117.7 (2) | F1—B1—F4 | 108.1 (9) |
N3—C10—H10A | 107.9 | F1A—B1—F3A | 106.1 (18) |
C11—C10—H10A | 107.9 | F4A—B1—F3A | 111.3 (18) |
N3—C10—H10B | 107.9 | F2A—B1—F3A | 102 (2) |
C11—C10—H10B | 107.9 | F7A—B2—F6A | 122 (3) |
H10A—C10—H10B | 107.2 | F7—B2—F8 | 115.4 (12) |
C16—C11—C12 | 117.7 (3) | F7—B2—F5 | 106.9 (13) |
C16—C11—C10 | 120.7 (4) | F8—B2—F5 | 110.6 (12) |
C12—C11—C10 | 121.4 (3) | F7A—B2—F5A | 111 (3) |
C13—C12—C11 | 120.3 (4) | F6A—B2—F5A | 105 (2) |
C13—C12—H12A | 119.9 | F7A—B2—F8A | 112.3 (16) |
C11—C12—H12A | 119.9 | F6A—B2—F8A | 107.4 (13) |
C14—C13—C12 | 121.2 (5) | F5A—B2—F8A | 97 (2) |
C14—C13—H13A | 119.4 | F7—B2—F6 | 105.5 (9) |
C12—C13—H13A | 119.4 | F8—B2—F6 | 109.6 (10) |
C15—C14—C13 | 119.6 (4) | F5—B2—F6 | 108.6 (12) |
C15—C14—H14A | 120.2 | ||
C6—N1—C2—C3 | −2.1 (5) | C22—N5—C18—C19 | 7.0 (6) |
Ni1—N1—C2—C3 | 173.2 (3) | Ni1—N5—C18—C19 | −155.3 (4) |
C6—N1—C2—C1 | 177.5 (3) | C22—N5—C18—C17 | −170.0 (4) |
Ni1—N1—C2—C1 | −7.2 (5) | Ni1—N5—C18—C17 | 27.7 (6) |
N1—C2—C3—C4 | 1.4 (6) | N5—C18—C19—C20 | −0.4 (8) |
C1—C2—C3—C4 | −178.2 (4) | C17—C18—C19—C20 | 176.6 (5) |
C2—C3—C4—C5 | −0.2 (7) | C18—C19—C20—C21 | −5.4 (9) |
C3—C4—C5—C6 | −0.2 (7) | C19—C20—C21—C22 | 4.5 (8) |
C2—N1—C6—C5 | 1.7 (5) | C18—N5—C22—C21 | −8.1 (6) |
Ni1—N1—C6—C5 | −174.5 (3) | Ni1—N5—C22—C21 | 158.1 (3) |
C2—N1—C6—C7 | −179.9 (3) | C18—N5—C22—C23 | 165.5 (3) |
Ni1—N1—C6—C7 | 3.8 (4) | Ni1—N5—C22—C23 | −28.3 (4) |
C4—C5—C6—N1 | −0.6 (7) | C20—C21—C22—N5 | 2.3 (7) |
C4—C5—C6—C7 | −178.9 (4) | C20—C21—C22—C23 | −171.1 (4) |
C24—N2—C7—C6 | 72.3 (3) | C9—N3—C23—C22 | 84.2 (3) |
C8—N2—C7—C6 | −164.3 (3) | C10—N3—C23—C22 | −152.9 (3) |
Ni1—N2—C7—C6 | −44.9 (3) | Ni1—N3—C23—C22 | −29.3 (3) |
N1—C6—C7—N2 | 27.5 (4) | N5—C22—C23—N3 | 41.5 (4) |
C5—C6—C7—N2 | −154.1 (4) | C21—C22—C23—N3 | −144.7 (4) |
C24—N2—C8—C9 | −78.0 (3) | C7—N2—C24—C25 | −142.1 (3) |
C7—N2—C8—C9 | 159.8 (3) | C8—N2—C24—C25 | 93.4 (3) |
Ni1—N2—C8—C9 | 41.8 (3) | Ni1—N2—C24—C25 | −26.5 (3) |
C23—N3—C9—C8 | −75.9 (3) | C29—N6—C25—C26 | −3.1 (4) |
C10—N3—C9—C8 | 162.3 (3) | Ni1—N6—C25—C26 | 167.6 (3) |
Ni1—N3—C9—C8 | 38.3 (3) | C29—N6—C25—C24 | 173.2 (3) |
N2—C8—C9—N3 | −55.1 (4) | Ni1—N6—C25—C24 | −16.2 (3) |
C23—N3—C10—C11 | −62.0 (4) | N2—C24—C25—N6 | 29.8 (4) |
C9—N3—C10—C11 | 60.2 (4) | N2—C24—C25—C26 | −153.7 (3) |
Ni1—N3—C10—C11 | 179.1 (3) | N6—C25—C26—C27 | 2.9 (5) |
N3—C10—C11—C16 | −102.0 (4) | C24—C25—C26—C27 | −173.3 (3) |
N3—C10—C11—C12 | 82.8 (4) | C25—C26—C27—C28 | −0.7 (6) |
C16—C11—C12—C13 | −0.5 (5) | C26—C27—C28—C29 | −1.3 (6) |
C10—C11—C12—C13 | 174.8 (3) | C25—N6—C29—C28 | 1.0 (4) |
C11—C12—C13—C14 | 0.3 (6) | Ni1—N6—C29—C28 | −167.1 (2) |
C12—C13—C14—C15 | 0.2 (7) | C25—N6—C29—C30 | −179.0 (3) |
C13—C14—C15—C16 | −0.5 (8) | Ni1—N6—C29—C30 | 13.0 (4) |
C12—C11—C16—C15 | 0.2 (6) | C27—C28—C29—N6 | 1.1 (5) |
C10—C11—C16—C15 | −175.1 (4) | C27—C28—C29—C30 | −178.9 (4) |
C14—C15—C16—C11 | 0.2 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1C···N4 | 0.96 | 2.94 | 3.251 (6) | 100 |
C3—H3A···F8i | 0.93 | 2.57 | 3.457 (14) | 159 |
C8—H8B···F7 | 0.97 | 2.57 | 3.371 (13) | 140 |
C8—H8B···F5A | 0.97 | 2.42 | 3.36 (4) | 163 |
C9—H9B···F4ii | 0.97 | 2.61 | 3.291 (16) | 128 |
C10—H10A···N6 | 0.97 | 2.67 | 3.273 (5) | 1213 |
C12—H12A···F8Aiii | 0.93 | 2.53 | 3.35 (2) | 146 |
C17—H17B···N1 | 0.96 | 2.64 | 3.071 (7) | 108 |
C21—H21A···F3ii | 0.93 | 2.62 | 3.122 (10) | 114 |
C23—H23B···F6Aiii | 0.97 | 2.33 | 3.241 (16) | 157 |
C24—H24A···F7 | 0.97 | 2.53 | 3.443 (15) | 156 |
C24—H24B···F3iv | 0.97 | 2.32 | 3.179 (13) | 148 |
C24—H24B···F1Aiv | 0.97 | 2.54 | 3.43 (3) | 153 |
C28—H28A···F4iii | 0.93 | 2.59 | 3.345 (19) | 138 |
C30—H30A···F4iii | 0.96 | 2.60 | 3.390 (17) | 140 |
C30—H30A···F4Aiii | 0.96 | 2.50 | 3.26 (3) | 136 |
C30—H30B···N4 | 0.96 | 2.85 | 3.126 (6) | 98 |
C32—H32A···F6iii | 0.96 | 2.40 | 3.196 (14) | 140 |
C32—H32A···F7Aiii | 0.96 | 2.33 | 3.19 (3) | 150 |
C32—H32B···F3v | 0.96 | 2.55 | 3.145 (15) | 121 |
C32—H32B···F3Av | 0.96 | 2.32 | 3.11 (4) | 140 |
Symmetry codes: (i) x+1/2, −y−1/2, z−1/2; (ii) x+1, −y, z+1/2; (iii) x+1, y, z; (iv) x+1/2, y−1/2, z; (v) x+3/2, y−1/2, z. |
Funding information
Funding for this research was provided by: China Postdoctoral Science Foundationhttps://doi.org/10.13039/501100002858 (award Nos. 2015M582573, Chinese National Natural Science Foundation, 21601164, 21573200, 21573223).
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