research communications
Nickel(II) carbonyl, ammonia, and acetonitrile complexes supported by a pyridine dipyrrolide pincer ligand
aDepartment of Chemistry and Biochemistry, The University of Texas at Arlington, Arlington, Texas 76019, USA
*Correspondence e-mail: dias@uta.edu
The synthesis, isolation and crystal structures of nickel(II) carbonyl, acetonitrile and ammonia complexes supported by a dianionic, pyridine dipyrrolide pincer ligand [pyrr2py]2−, namely, carbonyl[2,2′-(pyridine-2,6-diyl)bis(3,5-di-p-tolylpyrrolido-κN)]nickel(II), [Ni(C41H33N3)(CO)], ammine[2,2′-(pyridine-2,6-diyl)bis(3,5-di-p-tolylpyrrolido-κN)]nickel(II), [Ni(C41H33N3)(NH3)], and (acetonitrile-κN)[2,2′-(pyridine-2,6-diyl)bis(3,5-di-p-tolylpyrrolido-κN)]nickel(II), [Ni(C41H33N3)(CH3CN)], as well as the free ligand 2,6-bis(3,5-di-p-tolylpyrrol-2-yl)pyridine, C41H35N3 or [pyrr2py]H2 are reported. The nickel complexes are four-coordinate and adopt a square-planar geometry. The CO stretch of the nickel-bound carbon monoxide ligand of [pyrr2py]Ni(CO) has been observed at 2101 cm−1. The ammonia and acetonitrile complexes, [pyrr2py]Ni(NH3) and [pyrr2py]Ni(NCMe) feature all-nitrogen coordination spheres around nickel consisting of different N-donor ligand types.
Keywords: crystal structure; nickel; pincer ligand; N-donors; carbon monoxide.
1. Chemical context
Pincer ligands were first introduced by Moulton and Shaw in 1976 (Moulton & Shaw, 1976). They are utilized widely as auxiliary ligands to produce transition-metal complexes useful in a range of applications including catalysis (Alig et al., 2019; Peris & Crabtree, 2004, 2018; Piccirilli et al., 2020; Albrecht & van Koten, 2001). There are several pincer-ligand varieties in the literature ranging from those featuring both symmetric and non-symmetric flanking arms, P-, N-, O-, S- and C- donor sites, as well as neutral, mono, di- and trianionic systems. Monoanionic, carbon-centered (e.g., from phenyl) ligands with P- or N-donors at the flanking arms are more common among pincers (Peris & Crabtree, 2018). These tridentate ligands are particularly interesting for their ability to preferentially occupy the meridional coordination sites on a metal ion.
We have been working on tridentate, nitrogen-based ligands such as tris(pyrazolyl)borates with a preference for facial coordination for several years (Dias & Lovely, 2008; Dias et al., 1995, 1996; Dias & Lu, 1995). This paper describes results from our efforts to expand the ligand repertoire to include tridentate ligands with a preference for meridional geometry (Adiraju et al., 2020) at transition-metal ions in our laboratory. In particular, we describe the synthesis and use of a pyridine dipyrrolide pincer ligand bearing tolyl substituents, (Pramanik et al., 2014; Pramanik, 2015) and its chemistry with nickel(II) featuring CO, NH3 and NCMe molecules (Fig. 1). The pyridine dipyrrolide is a particularly attractive ligand framework, as several examples of pyridine dipyrrolide pincers with different substituents on the ligand backbone (e.g., Me, t-Bu, Ph, Mes) are known and have already been successfully used with both early and late transition-metal ions such as Ti (Zhang et al., 2016), Zr (Zhang et al., 2016, 2020), Cr (Gowda et al., 2018), Mo (Gowda et al., 2018), Fe (Sorsche et al., 2020; Hakey et al., 2019), Co (Grant et al., 2016), Pt (Komine et al., 2014), Pd (Yadav et al., 2018) and Zn (Komine et al., 2014) to form well-defined metal complexes.
2. Structural commentary
The free ligand [pyrr2Py]H2 is monomeric and crystallizes with both pyrrole nitrogen atoms facing the center of the coordination pit, well situated for metal-ion coordination (Fig. 2). This is different from the structure observed with the t-butyl substituted pincer analog (VIWSOL; Komine et al., 2014) in which one pyrrole N-H bond is directed outward to form a hydrogen bond with a lattice acetonitrile molecule. The pyrrole and pyridine moieties are essentially coplanar. The nickel(II) carbonyl complex [pyrr2Py]Ni(CO) was synthesized from the in situ-generated potassium salt K2[pyrr2Py] and Ni(OTf)2 in the presence of carbon monoxide. The important CO stretch of this molecule is observed at 2101 cm−1, which is only slightly lower than that of free CO (2143 cm−1), indicating relatively weak Ni→CO π-backbonding. The nickel(I) tris(pyrazolyl)borate complex [HB(3-Ph,5-MePz)3]Ni(CO) for comparison displays its CO stretch at 2003 cm−1 (Abubekerov et al., 2016). The X-ray shows that the pincer complex [pyrr2Py]Ni(CO) is a monomeric, square-planar complex (Fig. 3). The carbonyl moiety sits above the ligand plane, as is evident from the N1—Ni—C22 angle of 160.41 (13)°. The Ni—C22 distance of 1.809 (3) Å is significantly longer than the corresponding distance of 1.766 (4) Å in [HB(3-Ph,5-MePz)3]Ni(CO), which is a tetrahedral nickel complex (ENUROW; Abubekerov et al., 2016). The Ni—N(pyrr) (pyrr = pyrrolide) distances of 1.8667 (18) and 1.8666 (18) Å are not significantly different from the Ni—N(pyridine) separation of 1.853 (3) Å.
Compounds [pyrr2Py]Ni(NH3) and [pyrr2Py]Ni(NCMe) are also four-coordinate nickel(II) complexes with square-planar metal sites (Figs. 4 and 5, respectively). They have all nitrogen coordination spheres at nickel, but with an interesting variety of donor sites ranging from sp to sp3-hybridized nitrogen atoms, as well as neutral and formally anionic N-centers. Both the NH3 and NCMe ligands bend out of the [pyrr2Py] ligand plane as evident from the N2—Ni—N4 angles of 162.16 (5) and 168.09 (10)°, respectively, for the two complexes. The Ni—N1 and Ni—N3 bond distances of [pyrr2Py]Ni(NH3) are 1.8858 (10) and 1.8876 (10) Å, respectively. These values are marginally smaller than the corresponding distances of [pyrr2Py]Ni(NCMe) [1.896 (2) and 1.906 (2) Å]. The Ni—N2 distances (to the pyridine moieties) at 1.8490 (10) and 1.846 (2) Å are similar in the two adducts, but they are both much shorter than the Ni—N(pyrr) distances noted above. The Ni—N bond distance to the NH3 and NCMe ligands in [pyrr2Py]Ni(NH3) and [pyrr2Py]Ni(NCMe) are 1.9291 (11) and 1.861 (2) Å, respectively. These are bonds to sp3 and sp-hybridized nitrogen sites, respectively, and therefore the longer distance for the former is not unusual. Four-coordinate nickel–ammonia complexes are rare and there is one example in the CSD (PEWROZ; Tapper et al., 1993), and that has an Ni—N(H3) distance of 1.912 Å.
3. Supramolecular features
Important intermolecular contacts and a packing diagram of [pyrr2Py]H2 are shown in Fig. 6 and Fig. S1 in the supporting information. Neighboring molecules of [pyrr2Py]H2 show π–π contacts between pyrrole and pyridine groups (the closest separation is 3.21 Å) as well as C(arene)—H⋯arene contacts. The complex [pyrr2Py]Ni(CO) does not show extensive intermolecular interactions apart from NiCO⋯H—C(arene) contacts between the carbonyl moieties and hydrogen atoms of neighboring arene as illustrated in Fig. 7 and Fig. S2. In the structure of [pyrr2Py]Ni(NH3), the arene groups interact with neighboring molecules via the ammonia hydrogen atoms (see Fig. 8 and Fig. S3). In [pyrr2Py]Ni(NCMe), the hexane molecules in the lattice occupy regions surrounded by tolyl substituents. The major intermolecular interactions are between and the hydrogen atoms of the acetonitrile moieties. The resulting packing diagram is shown in Fig. 9 and Fig. S4.
4. Database survey
A search of the Cambridge Structural Database for related pyridine dipyrrolide complexes involving transition-metal ions revealed 38 hits involving ligands with different alkyl or aryl substituents (CSD Version 5.41, Update 2, May 2020; Groom et al., 2016). No nickel pyridine dipyrrolide complexes have been reported thus far. Perhaps the most closely related compounds are the four-coordinate platinum (VIWSIF; Komine et al., 2014), palladium (XIKKIO, XIKKOU; Yadav et al., 2018) and zinc (VIWSIF; Komine et al., 2014) complexes featuring all-nitrogen coordination spheres at the metal. In addition, there are ten hits for related free ligands. Most of them, however, are different solvates of the same ligand system.
5. Synthesis and crystallization
All experiments were done under a purified nitrogen atmosphere with standard Schlenk techniques. Solvents were purchased from commercial sources and purified using an Innovative Technology SPS-400 PureSolv solvent-drying system or distilled over conventional drying agents and degassed by the freeze–pump–thaw method three times prior to use. All other chemicals needed were obtained from commercial vendors. Glassware was oven dried at 150°C overnight. The NMR spectra were recorded at 25°C on JEOL Eclipse 500 and 300 spectrometers (1H: 500.16 MHz or 300.53 MHz). Proton chemical shifts are reported in ppm versus Me4Si. Infrared spectra were taken on a JASCO FT–IR 410 spectrometer.
Synthesis of 2,6-bis(3,5-ditolyl-2-pyrrolyl)pyridine, [pyrr2Py]H2:
1,3-Bis(4-tolyl)-2-propen-1-one (chalcone) was prepared following a literature procedure (Yang et al., 2005) from tolualdehyde and 4-methylacetophenone. Then the chalcone (1.75 g, 7.4 mmol) was reacted with 2,6-pyridinedicarbaldehyde (0.50 g, 3.7 mmol), 3-benzyl-5-(-hydroxyethyl)-4-methylthiazolium chloride (0.20 g, 0.74 mmol) and sodium t-butoxide (0.57 g, 0.74 mmol) in ethanol at reflux for 24 h to form a brown suspension. Water was added and the mixture was extracted with chloroform. The chloroform was removed to obtain 2,6-bis(2,4-ditolyl-1,4-dioxobutyl)pyridine. This was purified further by rinsing with hexane to get an orange solid. The intermediate ketone was reacted with NH4OAc (2.8 g, 37 mmol) in ethanol at reflux for 24 h. Water was added and the yellow solid was filtered and washed with water. Then the crude product was suspended in 10 mL of ethanol and refluxed at 373 K for 7 h to obtain 2,6-bis(3,5-ditolyl-2-pyrrolyl)pyridine, [pyrr2Py]H2 as a yellow solid (yield 64%). 1H NMR (CDCl3, 500.16 MHz, 298 K): δ 2.38 (s, 12H, CH3) 6.57 (m, 2H), 7.02 (d, J = 8.05, 2H), 7.17–7.22 (m, 9H), 7.38 (d, 4H), 7.47 (d, J = 8 Hz, 4H), 9.56 (2H, NH).
Synthesis of [pyrr2Py]Ni(NCCH3):
A solid sample of the ligand 2,6-bis(3,5-ditolyl-2-pyrrolyl)pyridine ([pyrr2Py]H2; 0.10 g, 0.175 mmol) and KH (0.021 g, 0.525 mmol) were placed in a 50 mL Schlenk flask. THF (ca 10 mL) was added to the mixture at room temperature and then refluxed for 1.5 h. It was allowed to cool down to room temperature and filtered through a Celite pad, which was then washed with 5 mL of THF. The filtrate was collected and added to Ni(OTf)2 (0.062 g, 0.175 mmol) in 10 mL of THF and stirred overnight at room temperature. The volatile materials were removed under reduced pressure and the residue was extracted into ether and filtered. Ether was removed under vacuum and 10 mL of acetonitrile were added. After 1 h, it was filtered, and the filtrate was concentrated to 4 mL. Finally, hexane was layered above the acetonitrile and allowed to diffuse slowly into acetonitrile solution at room temperature, producing brown crystals of [pyrr2Py]Ni(CH3CN) (yield 34%). 1H NMR (CDCl3, 500.16 MHz, 298 K): δ 0.738 (s, 3H, CH3) 2.32 (s, 6H, CH3), 2.37 (s, 6H, CH3) 6.06 (s, 2H), 6.60 (d, J = 8 Hz, 2H), 7.04 (t, J = 8 Hz, 1H), 7.15 (m, 8H), 7.36 (d, J = 8 Hz, 4H), 7.62 (d, J = 8.05 Hz, 4H).
Synthesis of [pyrr2Py]Ni(CO):
A solid sample of the ligand 2,6-bis(3,5-ditolyl-2-pyrrolyl)pyridine ([pyrr2Py]H2) (0.10 g, 0.175 mmol) and KH (0.021 g, 0.525 mmol) were placed in a 50 mL Schlenk flask. THF (ca 10 mL) was added to the mixture at room temperature and then refluxed for 1.5 h. It was allowed to cool down to room temperature and filtered through a Celite pad, which was then washed with 5 mL of THF. The filtrate was added to Ni(OTf)2 (0.062 g, 0.175 mmol) in 10 mL of THF and stirred overnight at room temperature. Then THF was removed and the residue was extracted into ether. Then anhydrous carbon monoxide gas was passed through the ether solution for 20 minutes at 273 K. After stirring for 1 h, the solution was filtered, and the volume of the solution was decreased to 4 mL. Red crystals of [pyrr2Py]Ni(CO) were observed after keeping the solution in a 253 K freezer for 3 d (yield 24%). 1H NMR (CDCl3, 500.16 MHz, 298 K): δ 2.37 (s, 6H, CH3), 2.38 (s, 6H, CH3) 6.21 (s, 2H), 6.77 (d, J = 7.45 Hz, 2H), 7.02 (t, J = 8 Hz, 1H), 7.21 (m, 8H), 7.38 (d, J = 7.5 Hz, 4H), 7.47 (d, J = 8.05 Hz, 4H). 13C{1H} NMR (CDCl3, 125.77 MHz, 298 K, selected): δ 174.4 (CO). IR (crystals, ATR, selected band) cm−1: 2101 (CO).
Synthesis of [pyrr2Py]Ni(NH3):
A solid sample of the ligand 2,6-bis(3,5-ditolyl-2-pyrrolyl)pyridine ([pyrr2Py]H2) (0.10 g, 0.175 mmol) and KH (0.021 g, 0.525 mmol) were placed in a 50 mL Schlenk flask. THF (ca 10 mL) was added to the mixture at room temperature and then refluxed for 1.5 h. It was allowed to cool down to room temperature and filtered through a Celite pad, which was then washed with 5 mL of THF. The filtrate was added to Ni(OTf)2 (0.062 g, 0.175 mmol) in 10 mL of THF and stirred overnight at room temperature. Then THF was removed and the residue was extracted into ether. Then anhydrous ammonia gas was passed through the ether solution for 20 minutes at 273 K. After stirring for 1 h, the solution was filtered, and the volume of the solution was decreased to 4 mL. Red crystals of [pyrr2Py]Ni(NH3) were formed after keeping the solution in a 253 K freezer for 3 d (yield 54%). 1H NMR (CDCl3, 500.16 MHz, 298 K): δ 0.49 (s, 3H, NH3) 2.35 (s, 6H, CH3), 2.38 (s, 6H, CH3) 6.08 (s, 2H), 6.63 (d, J = 8 Hz, 2H), 7.05 (t, J = 8.05 Hz, 1H), 7.19 (m, 8H), 7.36 (d, J = 8.05, 4H), 7.62 (d, J = 7.45 Hz, 4H). IR (crystals, ATR, selected bands) cm−1: 3310, 3360 (NH).
6. Refinement
Crystal data, data collection and structure 2Py]H2, [pyrr2Py]Ni(CO), [pyrr2Py]Ni(NH3) and [pyrr2Py]Ni(NCMe)·hexane are summarized in Table 1. Non-H atoms were refined with anisotropic displacement parameters. Hydrogen atoms, except for the N—H hydrogen atoms, were placed in calculated positions using riding models, and refined riding on their parent atoms with C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C) for aromatic hydrogen atoms, C—H = 0.99 Å and Uiso(H) = 1.2Ueq(C) for methylene hydrogen atoms (of hexane), and C—H = 0.98 Å with Uiso(H) = 1.5Ueq(C) for methyl hydrogen atoms. The N—H hydrogen atoms of [pyrr2Py]H2 and [pyrr2Py]Ni(NH3) were obtained from a difference-Fourier map and refined freely. The nickel carbonyl complex [pyrr2Py]Ni(CO) is located on a plane of symmetry containing the Ni–CO moiety but perpendicular to the [pyrr2Py] ligand plane, and consequently only a half is contained in the The complex [pyrr2Py]Ni(NCCH3) crystallizes with a molecule of hexane, which was disordered over two sites [with refined occupancy rates of 77.9 (5)% and 22.1 (5)%]. C—C bond distances were restrained to a target value of 1.53 (2) Å (DFIX restraint of SHELXL), 1,3 C⋯C distances were restrained to be similar to each other (SADI restraint of SHELXL, esd = 0.04 Å), and Uij components of ADPs were restrained to be similar for atoms closer to each other than two Å (SIMU restraint of SHELXL, esd = 0.02 Å2 for terminal atoms and 0.01 Å2 for all others).
details for [pyrrSupporting information
https://doi.org/10.1107/S2056989020013341/zl2799sup1.cif
contains datablocks pyrr2PyH2, pyrr2PyNiCO, pyrr2PyNiNH3, pyrr2PyNiCNMe. DOI:Structure factors: contains datablock pyrr2PyH2. DOI: https://doi.org/10.1107/S2056989020013341/zl2799pyrr2PyH2sup2.hkl
Structure factors: contains datablock pyrr2PyNiCO. DOI: https://doi.org/10.1107/S2056989020013341/zl2799pyrr2PyNiCOsup3.hkl
Structure factors: contains datablock pyrr2PyNiNH3. DOI: https://doi.org/10.1107/S2056989020013341/zl2799pyrr2PyNiNH3sup4.hkl
Structure factors: contains datablock pyrr2PyNiCNMe. DOI: https://doi.org/10.1107/S2056989020013341/zl2799pyrr2PyNiCNMesup5.hkl
For all structures, data collection: APEX3 (Bruker, 2016); cell
SAINT (Bruker, 2016); data reduction: SAINT Bruker, 2016); 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).C41H35N3 | F(000) = 1208 |
Mr = 569.72 | Dx = 1.237 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 14.8940 (15) Å | Cell parameters from 6014 reflections |
b = 35.155 (4) Å | θ = 3.0–28.0° |
c = 5.9513 (6) Å | µ = 0.07 mm−1 |
β = 100.987 (2)° | T = 100 K |
V = 3059.0 (5) Å3 | Plates, yellow |
Z = 4 | 0.28 × 0.18 × 0.12 mm |
Bruker D8 Quest with a Photon 100 CMOS detector diffractometer | 7596 independent reflections |
Radiation source: sealed tube | 5005 reflections with I > 2σ(I) |
Curved-graphite monochromator | Rint = 0.076 |
Detector resolution: 8 pixels mm-1 | θmax = 28.4°, θmin = 2.9° |
φ and ω scans | h = −19→19 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −46→46 |
Tmin = 0.341, Tmax = 0.431 | l = −7→7 |
31843 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.076 | Hydrogen site location: mixed |
wR(F2) = 0.182 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0644P)2 + 2.7619P] where P = (Fo2 + 2Fc2)/3 |
7596 reflections | (Δ/σ)max < 0.001 |
409 parameters | Δρmax = 0.40 e Å−3 |
0 restraints | Δρmin = −0.25 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 | ||
N1 | 0.31778 (13) | 0.41078 (6) | 0.3752 (4) | 0.0269 (5) | |
H1 | 0.3085 (17) | 0.3918 (8) | 0.284 (5) | 0.023 (7)* | |
N2 | 0.15143 (12) | 0.38454 (5) | 0.2069 (3) | 0.0220 (4) | |
N3 | 0.15725 (13) | 0.34057 (6) | −0.1524 (3) | 0.0218 (4) | |
H3 | 0.201 (2) | 0.3567 (8) | −0.090 (5) | 0.035 (8)* | |
C1 | 0.39793 (16) | 0.42861 (7) | 0.4672 (4) | 0.0284 (6) | |
C2 | 0.37801 (16) | 0.45430 (8) | 0.6255 (5) | 0.0309 (6) | |
H2 | 0.420528 | 0.470845 | 0.716611 | 0.037* | |
C3 | 0.28267 (16) | 0.45185 (7) | 0.6295 (4) | 0.0268 (5) | |
C4 | 0.24695 (15) | 0.42390 (7) | 0.4728 (4) | 0.0239 (5) | |
C5 | 0.48235 (16) | 0.41980 (7) | 0.3826 (5) | 0.0298 (6) | |
C6 | 0.47946 (18) | 0.40299 (9) | 0.1714 (5) | 0.0411 (7) | |
H6 | 0.421944 | 0.397431 | 0.077399 | 0.049* | |
C7 | 0.55943 (19) | 0.39409 (9) | 0.0944 (6) | 0.0422 (7) | |
H7 | 0.555510 | 0.382415 | −0.051101 | 0.051* | |
C8 | 0.64462 (17) | 0.40191 (8) | 0.2254 (5) | 0.0339 (6) | |
C9 | 0.64744 (19) | 0.41900 (10) | 0.4340 (6) | 0.0486 (8) | |
H9 | 0.705182 | 0.424893 | 0.525887 | 0.058* | |
C10 | 0.56826 (18) | 0.42799 (9) | 0.5151 (6) | 0.0456 (8) | |
H10 | 0.572601 | 0.439699 | 0.660598 | 0.055* | |
C11 | 0.73140 (18) | 0.39198 (9) | 0.1421 (6) | 0.0419 (7) | |
H11A | 0.778705 | 0.410843 | 0.199197 | 0.063* | |
H11B | 0.719407 | 0.391943 | −0.025612 | 0.063* | |
H11C | 0.752380 | 0.366705 | 0.198732 | 0.063* | |
C12 | 0.23419 (16) | 0.47692 (7) | 0.7652 (4) | 0.0257 (5) | |
C13 | 0.27181 (17) | 0.48578 (7) | 0.9915 (4) | 0.0304 (6) | |
H13 | 0.329417 | 0.475331 | 1.059455 | 0.036* | |
C14 | 0.22680 (19) | 0.50962 (8) | 1.1203 (5) | 0.0327 (6) | |
H14 | 0.253710 | 0.514926 | 1.274969 | 0.039* | |
C15 | 0.14287 (18) | 0.52581 (7) | 1.0254 (5) | 0.0299 (6) | |
C16 | 0.10546 (17) | 0.51734 (7) | 0.7991 (5) | 0.0286 (6) | |
H16 | 0.048060 | 0.528006 | 0.731306 | 0.034* | |
C17 | 0.15026 (16) | 0.49357 (7) | 0.6694 (5) | 0.0265 (5) | |
H17 | 0.123589 | 0.488589 | 0.514138 | 0.032* | |
C18 | 0.0944 (2) | 0.55256 (8) | 1.1610 (5) | 0.0396 (7) | |
H18A | 0.106102 | 0.578898 | 1.120927 | 0.059* | |
H18B | 0.117200 | 0.548580 | 1.324950 | 0.059* | |
H18C | 0.028499 | 0.547566 | 1.125210 | 0.059* | |
C19 | 0.15686 (15) | 0.40612 (7) | 0.3944 (4) | 0.0226 (5) | |
C20 | 0.08401 (16) | 0.40989 (7) | 0.5100 (4) | 0.0247 (5) | |
H20 | 0.090314 | 0.424150 | 0.647765 | 0.030* | |
C21 | 0.00241 (16) | 0.39217 (7) | 0.4173 (4) | 0.0250 (5) | |
H21 | −0.048992 | 0.394936 | 0.489085 | 0.030* | |
C22 | −0.00481 (16) | 0.37054 (7) | 0.2219 (4) | 0.0245 (5) | |
H22 | −0.061207 | 0.358902 | 0.155506 | 0.029* | |
C23 | 0.07227 (15) | 0.36606 (6) | 0.1232 (4) | 0.0205 (5) | |
C24 | 0.07687 (15) | 0.34119 (7) | −0.0706 (4) | 0.0215 (5) | |
C25 | 0.01808 (15) | 0.31582 (7) | −0.2046 (4) | 0.0217 (5) | |
C26 | 0.06570 (15) | 0.30020 (7) | −0.3677 (4) | 0.0235 (5) | |
H26 | 0.042322 | 0.281964 | −0.481713 | 0.028* | |
C27 | 0.15233 (15) | 0.31619 (7) | −0.3319 (4) | 0.0219 (5) | |
C28 | −0.07829 (15) | 0.30748 (7) | −0.1857 (4) | 0.0220 (5) | |
C29 | −0.09980 (16) | 0.28944 (7) | 0.0044 (4) | 0.0258 (5) | |
H29 | −0.051897 | 0.280648 | 0.121771 | 0.031* | |
C30 | −0.18999 (17) | 0.28401 (7) | 0.0264 (4) | 0.0279 (5) | |
H30 | −0.202766 | 0.271797 | 0.159191 | 0.033* | |
C31 | −0.26155 (16) | 0.29607 (7) | −0.1417 (5) | 0.0279 (6) | |
C32 | −0.24067 (16) | 0.31310 (7) | −0.3364 (5) | 0.0300 (6) | |
H32 | −0.288788 | 0.321051 | −0.455786 | 0.036* | |
C33 | −0.15012 (16) | 0.31866 (7) | −0.3587 (4) | 0.0264 (5) | |
H33 | −0.137268 | 0.330214 | −0.493386 | 0.032* | |
C34 | −0.35951 (18) | 0.29081 (9) | −0.1141 (6) | 0.0425 (7) | |
H34A | −0.376282 | 0.311221 | −0.017785 | 0.064* | |
H34B | −0.365963 | 0.266169 | −0.041886 | 0.064* | |
H34C | −0.399856 | 0.291641 | −0.264779 | 0.064* | |
C35 | 0.23013 (15) | 0.31055 (7) | −0.4467 (4) | 0.0224 (5) | |
C36 | 0.21959 (17) | 0.29117 (7) | −0.6546 (4) | 0.0258 (5) | |
H36 | 0.161229 | 0.281478 | −0.722971 | 0.031* | |
C37 | 0.29340 (17) | 0.28587 (7) | −0.7625 (4) | 0.0274 (5) | |
H37 | 0.284801 | 0.272442 | −0.903541 | 0.033* | |
C38 | 0.38005 (16) | 0.29991 (7) | −0.6680 (4) | 0.0287 (6) | |
C39 | 0.39012 (16) | 0.31946 (8) | −0.4625 (5) | 0.0321 (6) | |
H39 | 0.448292 | 0.329511 | −0.395562 | 0.039* | |
C40 | 0.31675 (16) | 0.32462 (8) | −0.3528 (5) | 0.0295 (6) | |
H40 | 0.325632 | 0.337963 | −0.211463 | 0.035* | |
C41 | 0.46052 (19) | 0.29329 (9) | −0.7846 (5) | 0.0396 (7) | |
H41A | 0.505142 | 0.313831 | −0.744108 | 0.059* | |
H41B | 0.439234 | 0.292851 | −0.950850 | 0.059* | |
H41C | 0.489307 | 0.268885 | −0.734267 | 0.059* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0196 (10) | 0.0316 (12) | 0.0297 (12) | 0.0012 (8) | 0.0049 (8) | −0.0087 (10) |
N2 | 0.0167 (9) | 0.0257 (10) | 0.0240 (11) | 0.0030 (8) | 0.0051 (8) | 0.0003 (8) |
N3 | 0.0155 (9) | 0.0277 (11) | 0.0224 (10) | 0.0006 (8) | 0.0041 (8) | −0.0005 (8) |
C1 | 0.0197 (12) | 0.0332 (14) | 0.0315 (14) | 0.0017 (10) | 0.0025 (10) | −0.0049 (11) |
C2 | 0.0203 (12) | 0.0380 (14) | 0.0322 (14) | 0.0016 (10) | −0.0007 (10) | −0.0084 (12) |
C3 | 0.0214 (11) | 0.0311 (13) | 0.0270 (13) | 0.0054 (10) | 0.0023 (10) | −0.0012 (11) |
C4 | 0.0199 (11) | 0.0271 (12) | 0.0254 (13) | 0.0047 (9) | 0.0061 (9) | 0.0001 (10) |
C5 | 0.0203 (12) | 0.0307 (14) | 0.0385 (15) | 0.0021 (10) | 0.0062 (11) | −0.0067 (12) |
C6 | 0.0221 (13) | 0.0505 (18) | 0.0509 (19) | −0.0024 (12) | 0.0074 (12) | −0.0149 (15) |
C7 | 0.0290 (14) | 0.0495 (18) | 0.0504 (19) | −0.0028 (12) | 0.0130 (13) | −0.0179 (15) |
C8 | 0.0218 (12) | 0.0321 (14) | 0.0497 (18) | 0.0006 (10) | 0.0117 (12) | −0.0001 (13) |
C9 | 0.0199 (13) | 0.060 (2) | 0.063 (2) | −0.0009 (13) | 0.0015 (13) | −0.0137 (17) |
C10 | 0.0257 (14) | 0.060 (2) | 0.0500 (19) | −0.0005 (13) | 0.0037 (13) | −0.0205 (16) |
C11 | 0.0251 (14) | 0.0444 (17) | 0.060 (2) | −0.0001 (12) | 0.0179 (13) | 0.0017 (15) |
C12 | 0.0230 (12) | 0.0261 (13) | 0.0282 (13) | 0.0019 (9) | 0.0056 (10) | −0.0037 (10) |
C13 | 0.0276 (13) | 0.0338 (14) | 0.0286 (14) | 0.0050 (10) | 0.0023 (11) | −0.0023 (11) |
C14 | 0.0402 (15) | 0.0322 (14) | 0.0260 (14) | 0.0027 (11) | 0.0071 (11) | −0.0039 (11) |
C15 | 0.0355 (14) | 0.0259 (13) | 0.0317 (14) | 0.0020 (10) | 0.0147 (11) | 0.0011 (11) |
C16 | 0.0247 (12) | 0.0254 (13) | 0.0367 (15) | 0.0031 (10) | 0.0087 (11) | 0.0009 (11) |
C17 | 0.0225 (12) | 0.0258 (13) | 0.0309 (14) | −0.0005 (9) | 0.0042 (10) | −0.0027 (10) |
C18 | 0.0478 (17) | 0.0346 (15) | 0.0415 (17) | 0.0094 (13) | 0.0212 (14) | −0.0009 (13) |
C19 | 0.0213 (11) | 0.0215 (12) | 0.0253 (13) | 0.0028 (9) | 0.0052 (9) | 0.0015 (10) |
C20 | 0.0257 (12) | 0.0241 (12) | 0.0263 (13) | 0.0033 (9) | 0.0098 (10) | −0.0005 (10) |
C21 | 0.0226 (12) | 0.0227 (12) | 0.0333 (14) | 0.0036 (9) | 0.0141 (10) | 0.0010 (10) |
C22 | 0.0201 (11) | 0.0255 (12) | 0.0294 (13) | 0.0007 (9) | 0.0084 (10) | 0.0020 (10) |
C23 | 0.0184 (11) | 0.0225 (11) | 0.0213 (12) | 0.0020 (9) | 0.0054 (9) | 0.0039 (9) |
C24 | 0.0171 (10) | 0.0271 (12) | 0.0212 (12) | 0.0026 (9) | 0.0061 (9) | 0.0018 (10) |
C25 | 0.0185 (11) | 0.0248 (12) | 0.0216 (12) | 0.0003 (9) | 0.0032 (9) | 0.0028 (10) |
C26 | 0.0203 (11) | 0.0276 (13) | 0.0222 (12) | 0.0000 (9) | 0.0027 (9) | 0.0013 (10) |
C27 | 0.0176 (11) | 0.0266 (12) | 0.0211 (12) | 0.0023 (9) | 0.0029 (9) | 0.0024 (10) |
C28 | 0.0191 (11) | 0.0225 (12) | 0.0248 (12) | −0.0005 (9) | 0.0053 (9) | −0.0024 (9) |
C29 | 0.0228 (12) | 0.0309 (13) | 0.0234 (13) | −0.0007 (10) | 0.0037 (10) | 0.0013 (10) |
C30 | 0.0306 (13) | 0.0297 (13) | 0.0259 (13) | −0.0060 (10) | 0.0120 (11) | −0.0011 (10) |
C31 | 0.0202 (12) | 0.0278 (13) | 0.0381 (15) | −0.0033 (9) | 0.0114 (10) | −0.0069 (11) |
C32 | 0.0201 (12) | 0.0331 (14) | 0.0360 (15) | 0.0014 (10) | 0.0034 (10) | 0.0022 (11) |
C33 | 0.0202 (11) | 0.0322 (13) | 0.0276 (13) | −0.0003 (10) | 0.0071 (10) | 0.0039 (11) |
C34 | 0.0243 (14) | 0.0534 (18) | 0.0538 (19) | −0.0074 (12) | 0.0179 (13) | −0.0046 (15) |
C35 | 0.0195 (11) | 0.0249 (12) | 0.0231 (12) | 0.0058 (9) | 0.0048 (9) | 0.0038 (10) |
C36 | 0.0242 (12) | 0.0270 (13) | 0.0258 (13) | 0.0018 (9) | 0.0035 (10) | 0.0027 (10) |
C37 | 0.0302 (13) | 0.0299 (13) | 0.0234 (13) | 0.0052 (10) | 0.0082 (10) | −0.0003 (10) |
C38 | 0.0221 (12) | 0.0351 (14) | 0.0311 (14) | 0.0080 (10) | 0.0110 (10) | 0.0046 (11) |
C39 | 0.0160 (11) | 0.0453 (16) | 0.0359 (15) | 0.0023 (10) | 0.0071 (10) | −0.0037 (12) |
C40 | 0.0222 (12) | 0.0386 (15) | 0.0282 (14) | 0.0013 (10) | 0.0058 (10) | −0.0058 (11) |
C41 | 0.0289 (14) | 0.0569 (19) | 0.0368 (16) | 0.0090 (13) | 0.0158 (12) | 0.0023 (14) |
N1—H1 | 0.86 (3) | C19—C20 | 1.398 (3) |
N1—C1 | 1.367 (3) | C20—H20 | 0.9500 |
N1—C4 | 1.377 (3) | C20—C21 | 1.384 (3) |
N2—C19 | 1.339 (3) | C21—H21 | 0.9500 |
N2—C23 | 1.355 (3) | C21—C22 | 1.377 (3) |
N3—H3 | 0.89 (3) | C22—H22 | 0.9500 |
N3—C24 | 1.376 (3) | C22—C23 | 1.394 (3) |
N3—C27 | 1.360 (3) | C23—C24 | 1.460 (3) |
C1—C2 | 1.378 (4) | C24—C25 | 1.390 (3) |
C1—C5 | 1.474 (3) | C25—C26 | 1.417 (3) |
C2—H2 | 0.9500 | C25—C28 | 1.490 (3) |
C2—C3 | 1.427 (3) | C26—H26 | 0.9500 |
C3—C4 | 1.389 (3) | C26—C27 | 1.386 (3) |
C3—C12 | 1.474 (3) | C27—C35 | 1.466 (3) |
C4—C19 | 1.473 (3) | C28—C29 | 1.387 (3) |
C5—C6 | 1.382 (4) | C28—C33 | 1.393 (3) |
C5—C10 | 1.399 (4) | C29—H29 | 0.9500 |
C6—H6 | 0.9500 | C29—C30 | 1.387 (3) |
C6—C7 | 1.391 (4) | C30—H30 | 0.9500 |
C7—H7 | 0.9500 | C30—C31 | 1.382 (4) |
C7—C8 | 1.384 (4) | C31—C32 | 1.391 (4) |
C8—C9 | 1.372 (4) | C31—C34 | 1.510 (3) |
C8—C11 | 1.511 (4) | C32—H32 | 0.9500 |
C9—H9 | 0.9500 | C32—C33 | 1.394 (3) |
C9—C10 | 1.393 (4) | C33—H33 | 0.9500 |
C10—H10 | 0.9500 | C34—H34A | 0.9800 |
C11—H11A | 0.9800 | C34—H34B | 0.9800 |
C11—H11B | 0.9800 | C34—H34C | 0.9800 |
C11—H11C | 0.9800 | C35—C36 | 1.395 (3) |
C12—C13 | 1.392 (4) | C35—C40 | 1.395 (3) |
C12—C17 | 1.400 (3) | C36—H36 | 0.9500 |
C13—H13 | 0.9500 | C36—C37 | 1.388 (3) |
C13—C14 | 1.391 (4) | C37—H37 | 0.9500 |
C14—H14 | 0.9500 | C37—C38 | 1.396 (4) |
C14—C15 | 1.391 (4) | C38—C39 | 1.386 (4) |
C15—C16 | 1.388 (4) | C38—C41 | 1.513 (3) |
C15—C18 | 1.510 (4) | C39—H39 | 0.9500 |
C16—H16 | 0.9500 | C39—C40 | 1.388 (3) |
C16—C17 | 1.391 (3) | C40—H40 | 0.9500 |
C17—H17 | 0.9500 | C41—H41A | 0.9800 |
C18—H18A | 0.9800 | C41—H41B | 0.9800 |
C18—H18B | 0.9800 | C41—H41C | 0.9800 |
C18—H18C | 0.9800 | ||
C1—N1—H1 | 129.5 (17) | C21—C20—C19 | 117.8 (2) |
C1—N1—C4 | 111.0 (2) | C21—C20—H20 | 121.1 |
C4—N1—H1 | 119.0 (17) | C20—C21—H21 | 119.8 |
C19—N2—C23 | 119.21 (19) | C22—C21—C20 | 120.5 (2) |
C24—N3—H3 | 117.5 (18) | C22—C21—H21 | 119.8 |
C27—N3—H3 | 130.8 (18) | C21—C22—H22 | 120.7 |
C27—N3—C24 | 111.56 (19) | C21—C22—C23 | 118.7 (2) |
N1—C1—C2 | 106.8 (2) | C23—C22—H22 | 120.7 |
N1—C1—C5 | 120.2 (2) | N2—C23—C22 | 121.3 (2) |
C2—C1—C5 | 132.9 (2) | N2—C23—C24 | 114.15 (19) |
C1—C2—H2 | 125.8 | C22—C23—C24 | 124.5 (2) |
C1—C2—C3 | 108.5 (2) | N3—C24—C23 | 117.7 (2) |
C3—C2—H2 | 125.8 | N3—C24—C25 | 106.4 (2) |
C2—C3—C12 | 124.5 (2) | C25—C24—C23 | 135.9 (2) |
C4—C3—C2 | 106.6 (2) | C24—C25—C26 | 107.4 (2) |
C4—C3—C12 | 128.7 (2) | C24—C25—C28 | 126.4 (2) |
N1—C4—C3 | 107.1 (2) | C26—C25—C28 | 126.2 (2) |
N1—C4—C19 | 116.7 (2) | C25—C26—H26 | 126.0 |
C3—C4—C19 | 136.2 (2) | C27—C26—C25 | 108.1 (2) |
C6—C5—C1 | 121.3 (2) | C27—C26—H26 | 126.0 |
C6—C5—C10 | 117.9 (2) | N3—C27—C26 | 106.6 (2) |
C10—C5—C1 | 120.8 (2) | N3—C27—C35 | 121.5 (2) |
C5—C6—H6 | 119.5 | C26—C27—C35 | 131.9 (2) |
C5—C6—C7 | 121.0 (3) | C29—C28—C25 | 121.8 (2) |
C7—C6—H6 | 119.5 | C29—C28—C33 | 117.9 (2) |
C6—C7—H7 | 119.3 | C33—C28—C25 | 120.2 (2) |
C8—C7—C6 | 121.3 (3) | C28—C29—H29 | 119.4 |
C8—C7—H7 | 119.3 | C28—C29—C30 | 121.2 (2) |
C7—C8—C11 | 121.3 (3) | C30—C29—H29 | 119.4 |
C9—C8—C7 | 117.6 (2) | C29—C30—H30 | 119.5 |
C9—C8—C11 | 121.2 (3) | C31—C30—C29 | 121.1 (2) |
C8—C9—H9 | 119.0 | C31—C30—H30 | 119.5 |
C8—C9—C10 | 122.0 (3) | C30—C31—C32 | 118.1 (2) |
C10—C9—H9 | 119.0 | C30—C31—C34 | 120.8 (2) |
C5—C10—H10 | 119.9 | C32—C31—C34 | 121.1 (2) |
C9—C10—C5 | 120.1 (3) | C31—C32—H32 | 119.5 |
C9—C10—H10 | 119.9 | C31—C32—C33 | 120.9 (2) |
C8—C11—H11A | 109.5 | C33—C32—H32 | 119.5 |
C8—C11—H11B | 109.5 | C28—C33—C32 | 120.7 (2) |
C8—C11—H11C | 109.5 | C28—C33—H33 | 119.6 |
H11A—C11—H11B | 109.5 | C32—C33—H33 | 119.6 |
H11A—C11—H11C | 109.5 | C31—C34—H34A | 109.5 |
H11B—C11—H11C | 109.5 | C31—C34—H34B | 109.5 |
C13—C12—C3 | 121.0 (2) | C31—C34—H34C | 109.5 |
C13—C12—C17 | 117.7 (2) | H34A—C34—H34B | 109.5 |
C17—C12—C3 | 121.3 (2) | H34A—C34—H34C | 109.5 |
C12—C13—H13 | 119.3 | H34B—C34—H34C | 109.5 |
C14—C13—C12 | 121.4 (2) | C36—C35—C27 | 120.9 (2) |
C14—C13—H13 | 119.3 | C36—C35—C40 | 117.9 (2) |
C13—C14—H14 | 119.6 | C40—C35—C27 | 121.2 (2) |
C13—C14—C15 | 120.9 (3) | C35—C36—H36 | 119.6 |
C15—C14—H14 | 119.6 | C37—C36—C35 | 120.7 (2) |
C14—C15—C18 | 121.4 (3) | C37—C36—H36 | 119.6 |
C16—C15—C14 | 118.0 (2) | C36—C37—H37 | 119.4 |
C16—C15—C18 | 120.5 (2) | C36—C37—C38 | 121.3 (2) |
C15—C16—H16 | 119.3 | C38—C37—H37 | 119.4 |
C15—C16—C17 | 121.4 (2) | C37—C38—C41 | 120.9 (2) |
C17—C16—H16 | 119.3 | C39—C38—C37 | 117.9 (2) |
C12—C17—H17 | 119.6 | C39—C38—C41 | 121.3 (2) |
C16—C17—C12 | 120.7 (2) | C38—C39—H39 | 119.4 |
C16—C17—H17 | 119.6 | C38—C39—C40 | 121.2 (2) |
C15—C18—H18A | 109.5 | C40—C39—H39 | 119.4 |
C15—C18—H18B | 109.5 | C35—C40—H40 | 119.5 |
C15—C18—H18C | 109.5 | C39—C40—C35 | 121.1 (2) |
H18A—C18—H18B | 109.5 | C39—C40—H40 | 119.5 |
H18A—C18—H18C | 109.5 | C38—C41—H41A | 109.5 |
H18B—C18—H18C | 109.5 | C38—C41—H41B | 109.5 |
N2—C19—C4 | 114.3 (2) | C38—C41—H41C | 109.5 |
N2—C19—C20 | 122.3 (2) | H41A—C41—H41B | 109.5 |
C20—C19—C4 | 123.3 (2) | H41A—C41—H41C | 109.5 |
C19—C20—H20 | 121.1 | H41B—C41—H41C | 109.5 |
N1—C1—C2—C3 | 0.1 (3) | C15—C16—C17—C12 | 1.0 (4) |
N1—C1—C5—C6 | 19.5 (4) | C17—C12—C13—C14 | 1.5 (4) |
N1—C1—C5—C10 | −160.0 (3) | C18—C15—C16—C17 | 178.2 (2) |
N1—C4—C19—N2 | −12.1 (3) | C19—N2—C23—C22 | 3.1 (3) |
N1—C4—C19—C20 | 165.2 (2) | C19—N2—C23—C24 | −175.5 (2) |
N2—C19—C20—C21 | −3.7 (4) | C19—C20—C21—C22 | 2.2 (4) |
N2—C23—C24—N3 | −3.0 (3) | C20—C21—C22—C23 | 1.7 (4) |
N2—C23—C24—C25 | 176.4 (3) | C21—C22—C23—N2 | −4.5 (3) |
N3—C24—C25—C26 | 0.0 (3) | C21—C22—C23—C24 | 174.0 (2) |
N3—C24—C25—C28 | −178.2 (2) | C22—C23—C24—N3 | 178.4 (2) |
N3—C27—C35—C36 | −168.1 (2) | C22—C23—C24—C25 | −2.2 (4) |
N3—C27—C35—C40 | 11.4 (4) | C23—N2—C19—C4 | 178.4 (2) |
C1—N1—C4—C3 | 1.4 (3) | C23—N2—C19—C20 | 1.0 (3) |
C1—N1—C4—C19 | −178.1 (2) | C23—C24—C25—C26 | −179.5 (3) |
C1—C2—C3—C4 | 0.8 (3) | C23—C24—C25—C28 | 2.3 (4) |
C1—C2—C3—C12 | −175.3 (2) | C24—N3—C27—C26 | −0.3 (3) |
C1—C5—C6—C7 | −178.8 (3) | C24—N3—C27—C35 | −179.6 (2) |
C1—C5—C10—C9 | 179.1 (3) | C24—C25—C26—C27 | −0.1 (3) |
C2—C1—C5—C6 | −156.7 (3) | C24—C25—C28—C29 | −66.8 (3) |
C2—C1—C5—C10 | 23.7 (5) | C24—C25—C28—C33 | 111.5 (3) |
C2—C3—C4—N1 | −1.3 (3) | C25—C26—C27—N3 | 0.3 (3) |
C2—C3—C4—C19 | 178.1 (3) | C25—C26—C27—C35 | 179.5 (2) |
C2—C3—C12—C13 | −44.1 (4) | C25—C28—C29—C30 | 175.9 (2) |
C2—C3—C12—C17 | 133.9 (3) | C25—C28—C33—C32 | −176.0 (2) |
C3—C4—C19—N2 | 168.6 (3) | C26—C25—C28—C29 | 115.4 (3) |
C3—C4—C19—C20 | −14.1 (4) | C26—C25—C28—C33 | −66.3 (3) |
C3—C12—C13—C14 | 179.6 (2) | C26—C27—C35—C36 | 12.8 (4) |
C3—C12—C17—C16 | −179.7 (2) | C26—C27—C35—C40 | −167.8 (3) |
C4—N1—C1—C2 | −1.0 (3) | C27—N3—C24—C23 | 179.8 (2) |
C4—N1—C1—C5 | −178.1 (2) | C27—N3—C24—C25 | 0.2 (3) |
C4—C3—C12—C13 | 140.8 (3) | C27—C35—C36—C37 | −180.0 (2) |
C4—C3—C12—C17 | −41.2 (4) | C27—C35—C40—C39 | −179.6 (2) |
C4—C19—C20—C21 | 179.2 (2) | C28—C25—C26—C27 | 178.0 (2) |
C5—C1—C2—C3 | 176.7 (3) | C28—C29—C30—C31 | 0.6 (4) |
C5—C6—C7—C8 | −0.4 (5) | C29—C28—C33—C32 | 2.4 (4) |
C6—C5—C10—C9 | −0.4 (5) | C29—C30—C31—C32 | 1.4 (4) |
C6—C7—C8—C9 | −0.4 (5) | C29—C30—C31—C34 | −178.6 (2) |
C6—C7—C8—C11 | 179.6 (3) | C30—C31—C32—C33 | −1.5 (4) |
C7—C8—C9—C10 | 0.7 (5) | C31—C32—C33—C28 | −0.4 (4) |
C8—C9—C10—C5 | −0.3 (5) | C33—C28—C29—C30 | −2.5 (4) |
C10—C5—C6—C7 | 0.8 (5) | C34—C31—C32—C33 | 178.5 (2) |
C11—C8—C9—C10 | −179.2 (3) | C35—C36—C37—C38 | −0.4 (4) |
C12—C3—C4—N1 | 174.5 (2) | C36—C35—C40—C39 | −0.1 (4) |
C12—C3—C4—C19 | −6.1 (5) | C36—C37—C38—C39 | −0.2 (4) |
C12—C13—C14—C15 | −0.8 (4) | C36—C37—C38—C41 | 178.7 (2) |
C13—C12—C17—C16 | −1.6 (4) | C37—C38—C39—C40 | 0.6 (4) |
C13—C14—C15—C16 | 0.2 (4) | C38—C39—C40—C35 | −0.5 (4) |
C13—C14—C15—C18 | −178.3 (3) | C40—C35—C36—C37 | 0.6 (4) |
C14—C15—C16—C17 | −0.3 (4) | C41—C38—C39—C40 | −178.3 (3) |
[Ni(C41H33N3)(CO)] | F(000) = 684 |
Mr = 654.42 | Dx = 1.342 Mg m−3 |
Monoclinic, P121/m1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.6482 (4) Å | Cell parameters from 5886 reflections |
b = 27.1709 (18) Å | θ = 3.0–30.5° |
c = 9.1322 (6) Å | µ = 0.64 mm−1 |
β = 101.0700 (12)° | T = 100 K |
V = 1618.92 (18) Å3 | Plates, yellow |
Z = 2 | 0.36 × 0.27 × 0.05 mm |
Bruker D8 Quest with a Photon 100 CMOS detector diffractometer | 4080 independent reflections |
Radiation source: sealed tube | 3280 reflections with I > 2σ(I) |
Curved-graphite monochromator | Rint = 0.057 |
Detector resolution: 8 pixels mm-1 | θmax = 28.3°, θmin = 3.0° |
φ and ω scans | h = −8→8 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −36→36 |
Tmin = 0.859, Tmax = 1.000 | l = −12→12 |
18888 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.119 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0592P)2 + 0.9514P] where P = (Fo2 + 2Fc2)/3 |
4080 reflections | (Δ/σ)max < 0.001 |
222 parameters | Δρmax = 0.67 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
Ni | −0.04446 (6) | 0.750000 | 0.86705 (4) | 0.01505 (12) | |
O | −0.2636 (4) | 0.750000 | 0.5582 (3) | 0.0313 (6) | |
N1 | 0.1861 (4) | 0.750000 | 1.0178 (3) | 0.0161 (5) | |
N2 | −0.0255 (3) | 0.81813 (7) | 0.89233 (19) | 0.0169 (4) | |
C1 | 0.5450 (5) | 0.750000 | 1.2176 (4) | 0.0242 (7) | |
H1 | 0.670105 | 0.750000 | 1.288274 | 0.029* | |
C2 | 0.4567 (4) | 0.79465 (9) | 1.1677 (3) | 0.0218 (5) | |
H2 | 0.519973 | 0.824808 | 1.203580 | 0.026* | |
C3 | 0.2721 (3) | 0.79438 (8) | 1.0632 (2) | 0.0170 (4) | |
C4 | 0.1516 (3) | 0.83425 (8) | 0.9875 (2) | 0.0183 (5) | |
C5 | 0.1610 (3) | 0.88577 (8) | 0.9845 (2) | 0.0185 (5) | |
C6 | −0.0168 (3) | 0.90088 (8) | 0.8840 (2) | 0.0205 (5) | |
H6 | −0.055029 | 0.933942 | 0.858799 | 0.025* | |
C7 | −0.1264 (3) | 0.85917 (8) | 0.8283 (2) | 0.0179 (4) | |
C8 | 0.3181 (3) | 0.91905 (8) | 1.0691 (2) | 0.0185 (4) | |
C9 | 0.5277 (4) | 0.91026 (9) | 1.0823 (3) | 0.0221 (5) | |
H9 | 0.572595 | 0.882978 | 1.031925 | 0.027* | |
C10 | 0.6717 (4) | 0.94084 (9) | 1.1680 (3) | 0.0229 (5) | |
H10 | 0.813288 | 0.933585 | 1.176897 | 0.028* | |
C11 | 0.6134 (4) | 0.98169 (9) | 1.2407 (3) | 0.0221 (5) | |
C12 | 0.4036 (4) | 0.99210 (9) | 1.2217 (3) | 0.0233 (5) | |
H12 | 0.359528 | 1.020579 | 1.267031 | 0.028* | |
C13 | 0.2591 (4) | 0.96129 (8) | 1.1373 (3) | 0.0218 (5) | |
H13 | 0.117622 | 0.969085 | 1.125842 | 0.026* | |
C14 | 0.7677 (4) | 1.01476 (10) | 1.3376 (3) | 0.0294 (6) | |
H14A | 0.906304 | 1.002061 | 1.340151 | 0.044* | |
H14B | 0.739580 | 1.015472 | 1.439028 | 0.044* | |
H14C | 0.757029 | 1.048148 | 1.296201 | 0.044* | |
C15 | −0.3239 (3) | 0.85618 (8) | 0.7220 (2) | 0.0174 (4) | |
C16 | −0.3557 (4) | 0.88339 (8) | 0.5890 (3) | 0.0210 (5) | |
H16 | −0.250400 | 0.904361 | 0.568115 | 0.025* | |
C17 | −0.5400 (4) | 0.87994 (9) | 0.4874 (3) | 0.0242 (5) | |
H17 | −0.558525 | 0.898537 | 0.397741 | 0.029* | |
C18 | −0.6980 (4) | 0.84969 (10) | 0.5148 (3) | 0.0246 (5) | |
C19 | −0.6676 (4) | 0.82337 (9) | 0.6479 (3) | 0.0243 (5) | |
H19 | −0.773984 | 0.802848 | 0.669221 | 0.029* | |
C20 | −0.4837 (4) | 0.82661 (9) | 0.7504 (3) | 0.0218 (5) | |
H20 | −0.466766 | 0.808452 | 0.840810 | 0.026* | |
C21 | −0.8980 (4) | 0.84547 (13) | 0.4040 (3) | 0.0388 (7) | |
H21A | −0.898746 | 0.814872 | 0.347097 | 0.058* | |
H21B | −0.912385 | 0.873591 | 0.335568 | 0.058* | |
H21C | −1.012360 | 0.845229 | 0.457559 | 0.058* | |
C22 | −0.2023 (5) | 0.750000 | 0.6821 (4) | 0.0204 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni | 0.0181 (2) | 0.0143 (2) | 0.01106 (19) | 0.000 | −0.00126 (14) | 0.000 |
O | 0.0447 (16) | 0.0315 (14) | 0.0148 (12) | 0.000 | −0.0018 (11) | 0.000 |
N1 | 0.0188 (13) | 0.0167 (13) | 0.0115 (12) | 0.000 | −0.0003 (10) | 0.000 |
N2 | 0.0214 (10) | 0.0150 (9) | 0.0133 (9) | 0.0003 (7) | 0.0003 (7) | −0.0019 (7) |
C1 | 0.0263 (17) | 0.0288 (18) | 0.0135 (15) | 0.000 | −0.0058 (13) | 0.000 |
C2 | 0.0247 (12) | 0.0216 (12) | 0.0166 (11) | −0.0031 (9) | −0.0024 (9) | −0.0031 (9) |
C3 | 0.0239 (11) | 0.0160 (10) | 0.0106 (9) | 0.0006 (8) | 0.0020 (8) | −0.0007 (8) |
C4 | 0.0195 (11) | 0.0190 (11) | 0.0156 (10) | −0.0015 (9) | 0.0012 (8) | −0.0008 (8) |
C5 | 0.0216 (11) | 0.0168 (11) | 0.0169 (10) | −0.0008 (9) | 0.0032 (9) | −0.0010 (8) |
C6 | 0.0242 (12) | 0.0150 (10) | 0.0208 (11) | 0.0002 (9) | 0.0004 (9) | 0.0004 (9) |
C7 | 0.0203 (11) | 0.0179 (11) | 0.0145 (10) | 0.0019 (9) | 0.0009 (8) | 0.0008 (8) |
C8 | 0.0235 (11) | 0.0158 (10) | 0.0153 (10) | −0.0033 (9) | 0.0012 (8) | 0.0011 (8) |
C9 | 0.0252 (12) | 0.0207 (11) | 0.0212 (11) | −0.0025 (9) | 0.0066 (9) | −0.0023 (9) |
C10 | 0.0181 (11) | 0.0267 (12) | 0.0245 (12) | −0.0038 (9) | 0.0053 (9) | 0.0000 (10) |
C11 | 0.0236 (12) | 0.0207 (11) | 0.0209 (11) | −0.0062 (9) | 0.0019 (9) | 0.0033 (9) |
C12 | 0.0263 (12) | 0.0151 (11) | 0.0273 (12) | −0.0009 (9) | 0.0022 (10) | −0.0027 (9) |
C13 | 0.0196 (11) | 0.0164 (11) | 0.0278 (12) | −0.0008 (9) | 0.0001 (9) | 0.0005 (9) |
C14 | 0.0248 (13) | 0.0307 (14) | 0.0307 (13) | −0.0071 (10) | 0.0009 (10) | −0.0061 (11) |
C15 | 0.0198 (11) | 0.0157 (10) | 0.0157 (10) | 0.0025 (8) | 0.0007 (8) | −0.0027 (8) |
C16 | 0.0256 (12) | 0.0166 (11) | 0.0207 (11) | 0.0024 (9) | 0.0039 (9) | 0.0004 (9) |
C17 | 0.0288 (13) | 0.0256 (12) | 0.0171 (11) | 0.0091 (10) | 0.0022 (9) | 0.0021 (9) |
C18 | 0.0214 (12) | 0.0330 (14) | 0.0185 (11) | 0.0066 (10) | 0.0017 (9) | −0.0026 (10) |
C19 | 0.0213 (12) | 0.0306 (13) | 0.0215 (12) | −0.0017 (10) | 0.0051 (9) | −0.0017 (10) |
C20 | 0.0233 (12) | 0.0236 (12) | 0.0183 (11) | 0.0022 (9) | 0.0037 (9) | 0.0012 (9) |
C21 | 0.0231 (13) | 0.067 (2) | 0.0243 (13) | 0.0050 (13) | 0.0001 (10) | 0.0025 (14) |
C22 | 0.0260 (17) | 0.0165 (15) | 0.0185 (16) | 0.000 | 0.0039 (13) | 0.000 |
Ni—N1 | 1.853 (3) | C10—H10 | 0.9500 |
Ni—N2i | 1.8667 (18) | C10—C11 | 1.386 (3) |
Ni—N2 | 1.8666 (18) | C11—C12 | 1.401 (3) |
Ni—C22 | 1.809 (3) | C11—C14 | 1.515 (3) |
O—C22 | 1.126 (4) | C12—H12 | 0.9500 |
N1—C3i | 1.364 (2) | C12—C13 | 1.391 (3) |
N1—C3 | 1.364 (2) | C13—H13 | 0.9500 |
N2—C4 | 1.393 (3) | C14—H14A | 0.9800 |
N2—C7 | 1.373 (3) | C14—H14B | 0.9800 |
C1—H1 | 0.9500 | C14—H14C | 0.9800 |
C1—C2 | 1.386 (3) | C15—C16 | 1.402 (3) |
C1—C2i | 1.386 (3) | C15—C20 | 1.395 (3) |
C2—H2 | 0.9500 | C16—H16 | 0.9500 |
C2—C3 | 1.403 (3) | C16—C17 | 1.391 (3) |
C3—C4 | 1.442 (3) | C17—H17 | 0.9500 |
C4—C5 | 1.402 (3) | C17—C18 | 1.394 (4) |
C5—C6 | 1.411 (3) | C18—C19 | 1.391 (3) |
C5—C8 | 1.482 (3) | C18—C21 | 1.512 (3) |
C6—H6 | 0.9500 | C19—H19 | 0.9500 |
C6—C7 | 1.390 (3) | C19—C20 | 1.392 (3) |
C7—C15 | 1.478 (3) | C20—H20 | 0.9500 |
C8—C9 | 1.396 (3) | C21—H21A | 0.9800 |
C8—C13 | 1.398 (3) | C21—H21B | 0.9800 |
C9—H9 | 0.9500 | C21—H21C | 0.9800 |
C9—C10 | 1.390 (3) | ||
N1—Ni—N2 | 83.20 (6) | C11—C10—H10 | 119.2 |
N1—Ni—N2i | 83.20 (6) | C10—C11—C12 | 117.7 (2) |
N2—Ni—N2i | 165.18 (11) | C10—C11—C14 | 122.3 (2) |
C22—Ni—N1 | 160.41 (13) | C12—C11—C14 | 119.9 (2) |
C22—Ni—N2 | 97.39 (5) | C11—C12—H12 | 119.6 |
C22—Ni—N2i | 97.40 (6) | C13—C12—C11 | 120.8 (2) |
C3i—N1—Ni | 117.66 (13) | C13—C12—H12 | 119.6 |
C3—N1—Ni | 117.66 (13) | C8—C13—H13 | 119.4 |
C3i—N1—C3 | 124.2 (3) | C12—C13—C8 | 121.2 (2) |
C4—N2—Ni | 114.70 (15) | C12—C13—H13 | 119.4 |
C7—N2—Ni | 137.48 (15) | C11—C14—H14A | 109.5 |
C7—N2—C4 | 107.19 (18) | C11—C14—H14B | 109.5 |
C2—C1—H1 | 118.9 | C11—C14—H14C | 109.5 |
C2i—C1—H1 | 118.9 | H14A—C14—H14B | 109.5 |
C2i—C1—C2 | 122.2 (3) | H14A—C14—H14C | 109.5 |
C1—C2—H2 | 120.7 | H14B—C14—H14C | 109.5 |
C1—C2—C3 | 118.6 (2) | C16—C15—C7 | 120.5 (2) |
C3—C2—H2 | 120.7 | C20—C15—C7 | 121.4 (2) |
N1—C3—C2 | 118.2 (2) | C20—C15—C16 | 118.1 (2) |
N1—C3—C4 | 110.88 (19) | C15—C16—H16 | 119.7 |
C2—C3—C4 | 130.9 (2) | C17—C16—C15 | 120.6 (2) |
N2—C4—C3 | 112.82 (19) | C17—C16—H16 | 119.7 |
N2—C4—C5 | 109.72 (19) | C16—C17—H17 | 119.4 |
C5—C4—C3 | 137.4 (2) | C16—C17—C18 | 121.2 (2) |
C4—C5—C6 | 105.6 (2) | C18—C17—H17 | 119.4 |
C4—C5—C8 | 129.0 (2) | C17—C18—C21 | 121.4 (2) |
C6—C5—C8 | 125.5 (2) | C19—C18—C17 | 118.1 (2) |
C5—C6—H6 | 125.8 | C19—C18—C21 | 120.5 (2) |
C7—C6—C5 | 108.4 (2) | C18—C19—H19 | 119.4 |
C7—C6—H6 | 125.8 | C18—C19—C20 | 121.1 (2) |
N2—C7—C6 | 109.10 (19) | C20—C19—H19 | 119.4 |
N2—C7—C15 | 122.3 (2) | C15—C20—H20 | 119.6 |
C6—C7—C15 | 128.5 (2) | C19—C20—C15 | 120.9 (2) |
C9—C8—C5 | 122.2 (2) | C19—C20—H20 | 119.6 |
C9—C8—C13 | 117.6 (2) | C18—C21—H21A | 109.5 |
C13—C8—C5 | 120.2 (2) | C18—C21—H21B | 109.5 |
C8—C9—H9 | 119.5 | C18—C21—H21C | 109.5 |
C10—C9—C8 | 121.0 (2) | H21A—C21—H21B | 109.5 |
C10—C9—H9 | 119.5 | H21A—C21—H21C | 109.5 |
C9—C10—H10 | 119.2 | H21B—C21—H21C | 109.5 |
C11—C10—C9 | 121.5 (2) | O—C22—Ni | 166.1 (3) |
Ni—N1—C3—C2 | −174.47 (18) | C4—C5—C8—C9 | 45.6 (4) |
Ni—N1—C3—C4 | 4.0 (3) | C4—C5—C8—C13 | −135.3 (3) |
Ni—N2—C4—C3 | −7.8 (2) | C5—C6—C7—N2 | 1.1 (3) |
Ni—N2—C4—C5 | 173.14 (15) | C5—C6—C7—C15 | 178.8 (2) |
Ni—N2—C7—C6 | −170.94 (18) | C5—C8—C9—C10 | −177.0 (2) |
Ni—N2—C7—C15 | 11.1 (4) | C5—C8—C13—C12 | 177.7 (2) |
N1—Ni—N2—C4 | 7.95 (17) | C6—C5—C8—C9 | −135.8 (2) |
N1—Ni—N2—C7 | 177.3 (2) | C6—C5—C8—C13 | 43.2 (3) |
N1—Ni—C22—O | 0.000 (5) | C6—C7—C15—C16 | 48.5 (3) |
N1—C3—C4—N2 | 2.5 (3) | C6—C7—C15—C20 | −131.3 (3) |
N1—C3—C4—C5 | −178.9 (3) | C7—N2—C4—C3 | 179.68 (18) |
N2i—Ni—N1—C3i | 6.7 (2) | C7—N2—C4—C5 | 0.7 (3) |
N2i—Ni—N1—C3 | 179.2 (2) | C7—C15—C16—C17 | 178.8 (2) |
N2—Ni—N1—C3 | −6.7 (2) | C7—C15—C20—C19 | −178.7 (2) |
N2—Ni—N1—C3i | −179.2 (2) | C8—C5—C6—C7 | −179.5 (2) |
N2i—Ni—N2—C4 | 31.5 (6) | C8—C9—C10—C11 | −1.4 (4) |
N2i—Ni—N2—C7 | −159.1 (3) | C9—C8—C13—C12 | −3.2 (3) |
N2—Ni—C22—O | 90.49 (6) | C9—C10—C11—C12 | −1.8 (4) |
N2i—Ni—C22—O | −90.49 (6) | C9—C10—C11—C14 | 178.5 (2) |
N2—C4—C5—C6 | 0.0 (3) | C10—C11—C12—C13 | 2.4 (4) |
N2—C4—C5—C8 | 178.8 (2) | C11—C12—C13—C8 | 0.1 (4) |
N2—C7—C15—C16 | −134.0 (2) | C13—C8—C9—C10 | 3.9 (3) |
N2—C7—C15—C20 | 46.2 (3) | C14—C11—C12—C13 | −177.8 (2) |
C1—C2—C3—N1 | 1.2 (4) | C15—C16—C17—C18 | 0.3 (4) |
C1—C2—C3—C4 | −176.9 (3) | C16—C15—C20—C19 | 1.5 (3) |
C2i—C1—C2—C3 | −0.1 (5) | C16—C17—C18—C19 | 0.8 (4) |
C2—C3—C4—N2 | −179.3 (2) | C16—C17—C18—C21 | −179.4 (2) |
C2—C3—C4—C5 | −0.6 (5) | C17—C18—C19—C20 | −0.8 (4) |
C3i—N1—C3—C2 | −2.6 (4) | C18—C19—C20—C15 | −0.4 (4) |
C3i—N1—C3—C4 | 175.9 (2) | C20—C15—C16—C17 | −1.4 (3) |
C3—C4—C5—C6 | −178.7 (3) | C21—C18—C19—C20 | 179.5 (2) |
C3—C4—C5—C8 | 0.1 (5) | C22—Ni—N1—C3i | −86.2 (2) |
C4—N2—C7—C6 | −1.1 (3) | C22—Ni—N1—C3 | 86.2 (2) |
C4—N2—C7—C15 | −179.0 (2) | C22—Ni—N2—C4 | −152.32 (18) |
C4—C5—C6—C7 | −0.7 (3) | C22—Ni—N2—C7 | 17.0 (3) |
Symmetry code: (i) x, −y+3/2, z. |
[Ni(C41H33N3)(NH3)] | F(000) = 1352 |
Mr = 643.45 | Dx = 1.313 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 15.9773 (6) Å | Cell parameters from 9841 reflections |
b = 14.9441 (5) Å | θ = 3.0–39.4° |
c = 14.3238 (5) Å | µ = 0.63 mm−1 |
β = 107.8140 (8)° | T = 100 K |
V = 3256.1 (2) Å3 | Plates, red |
Z = 4 | 0.46 × 0.41 × 0.14 mm |
Bruker D8 Quest with a Photon 100 CMOS detector diffractometer | 8502 reflections with I > 2σ(I) |
Curved-graphite monochromator | Rint = 0.026 |
φ and ω scans | θmax = 30.5°, θmin = 2.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −22→22 |
Tmin = 0.858, Tmax = 0.967 | k = −21→21 |
48278 measured reflections | l = −20→20 |
9931 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.036 | Hydrogen site location: mixed |
wR(F2) = 0.098 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0562P)2 + 1.1192P] where P = (Fo2 + 2Fc2)/3 |
9931 reflections | (Δ/σ)max = 0.002 |
431 parameters | Δρmax = 0.51 e Å−3 |
0 restraints | Δρmin = −0.25 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 | ||
Ni | 0.10799 (2) | 0.41253 (2) | 0.93990 (2) | 0.01428 (5) | |
N1 | 0.21118 (7) | 0.43570 (7) | 0.90627 (7) | 0.01684 (19) | |
N2 | 0.05856 (7) | 0.39854 (7) | 0.80601 (7) | 0.01515 (19) | |
N3 | −0.00188 (7) | 0.36827 (7) | 0.94266 (7) | 0.01631 (19) | |
N4 | 0.14688 (8) | 0.46458 (8) | 1.06929 (8) | 0.0179 (2) | |
H4A | 0.1037 (17) | 0.4707 (17) | 1.0960 (18) | 0.060 (7)* | |
H4B | 0.1871 (18) | 0.4399 (19) | 1.1142 (19) | 0.063 (7)* | |
H4C | 0.1692 (16) | 0.5156 (18) | 1.0630 (17) | 0.056 (7)* | |
C1 | 0.29896 (8) | 0.45061 (9) | 0.94997 (9) | 0.0190 (2) | |
C2 | 0.33888 (8) | 0.47073 (10) | 0.87809 (10) | 0.0227 (3) | |
H2 | 0.399240 | 0.484362 | 0.889319 | 0.027* | |
C3 | 0.27366 (8) | 0.46719 (9) | 0.78618 (9) | 0.0188 (2) | |
C4 | 0.19592 (8) | 0.44495 (9) | 0.80609 (9) | 0.0171 (2) | |
C5 | 0.10722 (8) | 0.42434 (8) | 0.74805 (9) | 0.0162 (2) | |
C6 | 0.06831 (9) | 0.42720 (9) | 0.64636 (9) | 0.0185 (2) | |
H6 | 0.101605 | 0.443252 | 0.604162 | 0.022* | |
C7 | −0.02032 (9) | 0.40596 (9) | 0.60869 (9) | 0.0200 (2) | |
H7 | −0.047903 | 0.408038 | 0.539816 | 0.024* | |
C8 | −0.06959 (8) | 0.38168 (9) | 0.66984 (9) | 0.0190 (2) | |
H8 | −0.130417 | 0.368353 | 0.643358 | 0.023* | |
C9 | −0.02792 (8) | 0.37728 (8) | 0.77075 (9) | 0.0159 (2) | |
C10 | −0.06230 (8) | 0.35450 (8) | 0.85048 (9) | 0.0162 (2) | |
C11 | −0.14162 (8) | 0.32195 (8) | 0.86028 (9) | 0.0170 (2) | |
C12 | −0.12798 (8) | 0.31616 (9) | 0.96247 (9) | 0.0186 (2) | |
H12 | −0.169888 | 0.296952 | 0.993071 | 0.022* | |
C13 | −0.04184 (8) | 0.34373 (8) | 1.01047 (9) | 0.0172 (2) | |
C14 | 0.34369 (8) | 0.43631 (9) | 1.05496 (9) | 0.0196 (2) | |
C15 | 0.32402 (9) | 0.36205 (10) | 1.10428 (10) | 0.0225 (3) | |
H15 | 0.278667 | 0.322055 | 1.070416 | 0.027* | |
C16 | 0.37015 (10) | 0.34625 (10) | 1.20222 (10) | 0.0264 (3) | |
H16 | 0.354631 | 0.296548 | 1.234851 | 0.032* | |
C17 | 0.43869 (9) | 0.40205 (11) | 1.25325 (10) | 0.0273 (3) | |
C18 | 0.45818 (9) | 0.47588 (11) | 1.20459 (11) | 0.0274 (3) | |
H18 | 0.504218 | 0.515165 | 1.238430 | 0.033* | |
C19 | 0.41132 (9) | 0.49320 (10) | 1.10702 (10) | 0.0233 (3) | |
H19 | 0.425507 | 0.544340 | 1.075466 | 0.028* | |
C20 | 0.49213 (12) | 0.38050 (14) | 1.35736 (12) | 0.0393 (4) | |
H20A | 0.458982 | 0.339379 | 1.386063 | 0.059* | |
H20B | 0.504500 | 0.435775 | 1.395978 | 0.059* | |
H20C | 0.547612 | 0.352361 | 1.357653 | 0.059* | |
C21 | 0.28514 (8) | 0.48099 (9) | 0.68838 (9) | 0.0186 (2) | |
C22 | 0.32480 (11) | 0.41602 (10) | 0.64649 (11) | 0.0266 (3) | |
H22 | 0.346065 | 0.362588 | 0.681707 | 0.032* | |
C23 | 0.33372 (12) | 0.42831 (11) | 0.55354 (11) | 0.0308 (3) | |
H23 | 0.360985 | 0.383006 | 0.526433 | 0.037* | |
C24 | 0.30348 (10) | 0.50564 (10) | 0.49969 (10) | 0.0245 (3) | |
C25 | 0.26657 (10) | 0.57145 (10) | 0.54301 (10) | 0.0235 (3) | |
H25 | 0.247296 | 0.625774 | 0.508725 | 0.028* | |
C26 | 0.25718 (9) | 0.55955 (10) | 0.63571 (10) | 0.0231 (3) | |
H26 | 0.231342 | 0.605643 | 0.663410 | 0.028* | |
C27 | 0.31087 (14) | 0.51780 (13) | 0.39833 (12) | 0.0414 (4) | |
H27A | 0.362859 | 0.485913 | 0.393138 | 0.062* | |
H27B | 0.316402 | 0.581651 | 0.385761 | 0.062* | |
H27C | 0.258167 | 0.493772 | 0.350014 | 0.062* | |
C28 | 0.00284 (8) | 0.34193 (8) | 1.11671 (9) | 0.0179 (2) | |
C29 | −0.03979 (9) | 0.37551 (9) | 1.18122 (10) | 0.0215 (2) | |
H29 | −0.096129 | 0.402330 | 1.155903 | 0.026* | |
C30 | −0.00052 (11) | 0.37002 (9) | 1.28201 (10) | 0.0257 (3) | |
H30 | −0.031062 | 0.391957 | 1.324719 | 0.031* | |
C31 | 0.08258 (10) | 0.33305 (9) | 1.32141 (10) | 0.0254 (3) | |
C32 | 0.12548 (10) | 0.29963 (9) | 1.25727 (10) | 0.0238 (3) | |
H32 | 0.182468 | 0.274300 | 1.282871 | 0.029* | |
C33 | 0.08576 (9) | 0.30297 (9) | 1.15627 (9) | 0.0202 (2) | |
H33 | 0.115269 | 0.278520 | 1.113748 | 0.024* | |
C34 | 0.12424 (13) | 0.32882 (12) | 1.43072 (11) | 0.0371 (4) | |
H34A | 0.148744 | 0.387517 | 1.454991 | 0.056* | |
H34B | 0.171345 | 0.284084 | 1.446531 | 0.056* | |
H34C | 0.079770 | 0.312095 | 1.461879 | 0.056* | |
C35 | −0.22326 (8) | 0.29502 (8) | 0.78474 (9) | 0.0181 (2) | |
C36 | −0.22213 (8) | 0.24553 (9) | 0.70235 (10) | 0.0205 (2) | |
H36 | −0.167373 | 0.230297 | 0.693374 | 0.025* | |
C37 | −0.29980 (9) | 0.21818 (10) | 0.63324 (10) | 0.0235 (3) | |
H37 | −0.297210 | 0.184450 | 0.577976 | 0.028* | |
C38 | −0.38148 (9) | 0.23948 (10) | 0.64380 (11) | 0.0250 (3) | |
C39 | −0.38268 (9) | 0.28783 (10) | 0.72610 (11) | 0.0263 (3) | |
H39 | −0.437551 | 0.302475 | 0.735130 | 0.032* | |
C40 | −0.30516 (9) | 0.31540 (10) | 0.79584 (10) | 0.0232 (3) | |
H40 | −0.307994 | 0.348378 | 0.851496 | 0.028* | |
C41 | −0.46521 (10) | 0.20943 (12) | 0.56827 (12) | 0.0343 (3) | |
H41A | −0.480968 | 0.149536 | 0.585162 | 0.051* | |
H41B | −0.456395 | 0.207820 | 0.503525 | 0.051* | |
H41C | −0.512642 | 0.251416 | 0.567071 | 0.051* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni | 0.01402 (8) | 0.01717 (8) | 0.01271 (8) | −0.00050 (5) | 0.00565 (6) | 0.00038 (5) |
N1 | 0.0149 (5) | 0.0218 (5) | 0.0145 (4) | −0.0004 (4) | 0.0055 (4) | 0.0009 (4) |
N2 | 0.0152 (4) | 0.0168 (5) | 0.0146 (4) | 0.0003 (4) | 0.0063 (4) | 0.0006 (3) |
N3 | 0.0164 (5) | 0.0190 (5) | 0.0145 (4) | −0.0014 (4) | 0.0062 (4) | 0.0005 (4) |
N4 | 0.0192 (5) | 0.0189 (5) | 0.0165 (5) | −0.0006 (4) | 0.0070 (4) | −0.0003 (4) |
C1 | 0.0156 (5) | 0.0250 (6) | 0.0168 (5) | −0.0010 (4) | 0.0055 (4) | 0.0006 (5) |
C2 | 0.0157 (5) | 0.0339 (7) | 0.0198 (6) | −0.0026 (5) | 0.0074 (5) | 0.0014 (5) |
C3 | 0.0178 (5) | 0.0237 (6) | 0.0167 (5) | −0.0007 (4) | 0.0079 (4) | 0.0011 (4) |
C4 | 0.0168 (5) | 0.0205 (6) | 0.0151 (5) | −0.0002 (4) | 0.0064 (4) | 0.0011 (4) |
C5 | 0.0169 (5) | 0.0171 (5) | 0.0161 (5) | 0.0006 (4) | 0.0071 (4) | 0.0001 (4) |
C6 | 0.0214 (6) | 0.0206 (6) | 0.0151 (5) | −0.0011 (4) | 0.0080 (4) | −0.0001 (4) |
C7 | 0.0216 (6) | 0.0235 (6) | 0.0144 (5) | −0.0015 (5) | 0.0049 (5) | −0.0003 (4) |
C8 | 0.0172 (5) | 0.0227 (6) | 0.0166 (5) | −0.0015 (4) | 0.0045 (4) | −0.0003 (4) |
C9 | 0.0161 (5) | 0.0158 (5) | 0.0167 (5) | 0.0002 (4) | 0.0065 (4) | −0.0004 (4) |
C10 | 0.0161 (5) | 0.0179 (5) | 0.0154 (5) | −0.0003 (4) | 0.0061 (4) | −0.0003 (4) |
C11 | 0.0165 (5) | 0.0162 (5) | 0.0195 (5) | −0.0009 (4) | 0.0072 (4) | −0.0010 (4) |
C12 | 0.0196 (6) | 0.0191 (6) | 0.0198 (5) | −0.0020 (4) | 0.0099 (5) | 0.0007 (4) |
C13 | 0.0202 (5) | 0.0169 (5) | 0.0168 (5) | −0.0004 (4) | 0.0089 (4) | 0.0006 (4) |
C14 | 0.0145 (5) | 0.0274 (6) | 0.0175 (5) | 0.0028 (5) | 0.0057 (4) | 0.0004 (5) |
C15 | 0.0199 (6) | 0.0261 (7) | 0.0210 (6) | 0.0009 (5) | 0.0056 (5) | 0.0010 (5) |
C16 | 0.0259 (7) | 0.0308 (7) | 0.0224 (6) | 0.0046 (5) | 0.0074 (5) | 0.0052 (5) |
C17 | 0.0211 (6) | 0.0423 (9) | 0.0177 (6) | 0.0060 (6) | 0.0047 (5) | −0.0007 (5) |
C18 | 0.0181 (6) | 0.0398 (8) | 0.0230 (6) | −0.0020 (5) | 0.0044 (5) | −0.0058 (6) |
C19 | 0.0179 (6) | 0.0303 (7) | 0.0222 (6) | −0.0013 (5) | 0.0071 (5) | −0.0014 (5) |
C20 | 0.0319 (8) | 0.0580 (11) | 0.0229 (7) | 0.0069 (8) | 0.0007 (6) | 0.0023 (7) |
C21 | 0.0162 (5) | 0.0238 (6) | 0.0173 (5) | −0.0025 (4) | 0.0075 (4) | 0.0002 (4) |
C22 | 0.0366 (8) | 0.0233 (7) | 0.0228 (6) | 0.0056 (5) | 0.0137 (6) | 0.0039 (5) |
C23 | 0.0443 (9) | 0.0289 (7) | 0.0246 (7) | 0.0100 (6) | 0.0186 (6) | 0.0018 (5) |
C24 | 0.0297 (7) | 0.0277 (7) | 0.0194 (6) | 0.0019 (5) | 0.0122 (5) | 0.0017 (5) |
C25 | 0.0269 (7) | 0.0246 (6) | 0.0199 (6) | 0.0028 (5) | 0.0082 (5) | 0.0038 (5) |
C26 | 0.0253 (6) | 0.0255 (6) | 0.0211 (6) | 0.0049 (5) | 0.0107 (5) | 0.0012 (5) |
C27 | 0.0639 (12) | 0.0437 (10) | 0.0251 (7) | 0.0160 (9) | 0.0263 (8) | 0.0079 (7) |
C28 | 0.0229 (6) | 0.0163 (5) | 0.0165 (5) | −0.0031 (4) | 0.0089 (5) | 0.0011 (4) |
C29 | 0.0277 (6) | 0.0182 (6) | 0.0220 (6) | −0.0020 (5) | 0.0126 (5) | 0.0005 (5) |
C30 | 0.0409 (8) | 0.0204 (6) | 0.0208 (6) | −0.0034 (5) | 0.0169 (6) | −0.0027 (5) |
C31 | 0.0396 (8) | 0.0198 (6) | 0.0168 (6) | −0.0074 (5) | 0.0085 (5) | 0.0002 (5) |
C32 | 0.0269 (6) | 0.0232 (6) | 0.0193 (6) | −0.0029 (5) | 0.0042 (5) | 0.0026 (5) |
C33 | 0.0246 (6) | 0.0194 (6) | 0.0182 (5) | −0.0022 (5) | 0.0091 (5) | 0.0015 (4) |
C34 | 0.0552 (10) | 0.0357 (8) | 0.0172 (6) | −0.0063 (7) | 0.0062 (7) | 0.0004 (6) |
C35 | 0.0162 (5) | 0.0183 (6) | 0.0210 (6) | −0.0011 (4) | 0.0074 (4) | 0.0016 (4) |
C36 | 0.0172 (5) | 0.0216 (6) | 0.0239 (6) | −0.0020 (4) | 0.0080 (5) | −0.0016 (5) |
C37 | 0.0227 (6) | 0.0250 (6) | 0.0228 (6) | −0.0056 (5) | 0.0070 (5) | −0.0015 (5) |
C38 | 0.0183 (6) | 0.0282 (7) | 0.0270 (6) | −0.0067 (5) | 0.0049 (5) | 0.0054 (5) |
C39 | 0.0160 (6) | 0.0327 (7) | 0.0319 (7) | −0.0012 (5) | 0.0099 (5) | 0.0030 (6) |
C40 | 0.0192 (6) | 0.0274 (7) | 0.0264 (6) | −0.0011 (5) | 0.0120 (5) | −0.0003 (5) |
C41 | 0.0215 (7) | 0.0433 (9) | 0.0332 (8) | −0.0101 (6) | 0.0011 (6) | 0.0045 (7) |
Ni—N1 | 1.8858 (10) | C20—H20A | 0.9800 |
Ni—N2 | 1.8490 (10) | C20—H20B | 0.9800 |
Ni—N3 | 1.8876 (10) | C20—H20C | 0.9800 |
Ni—N4 | 1.9291 (11) | C21—C22 | 1.3917 (19) |
N1—C1 | 1.3679 (16) | C21—C26 | 1.3932 (19) |
N1—C4 | 1.3871 (15) | C22—H22 | 0.9500 |
N2—C5 | 1.3554 (15) | C22—C23 | 1.394 (2) |
N2—C9 | 1.3558 (16) | C23—H23 | 0.9500 |
N3—C10 | 1.3920 (15) | C23—C24 | 1.391 (2) |
N3—C13 | 1.3655 (15) | C24—C25 | 1.3871 (19) |
N4—H4A | 0.89 (3) | C24—C27 | 1.5033 (19) |
N4—H4B | 0.84 (3) | C25—H25 | 0.9500 |
N4—H4C | 0.86 (3) | C25—C26 | 1.3925 (18) |
C1—C2 | 1.3996 (17) | C26—H26 | 0.9500 |
C1—C14 | 1.4699 (17) | C27—H27A | 0.9800 |
C2—H2 | 0.9500 | C27—H27B | 0.9800 |
C2—C3 | 1.4080 (18) | C27—H27C | 0.9800 |
C3—C4 | 1.3968 (17) | C28—C29 | 1.3981 (17) |
C3—C21 | 1.4818 (17) | C28—C33 | 1.3986 (19) |
C4—C5 | 1.4400 (17) | C29—H29 | 0.9500 |
C5—C6 | 1.3986 (17) | C29—C30 | 1.3894 (19) |
C6—H6 | 0.9500 | C30—H30 | 0.9500 |
C6—C7 | 1.3891 (18) | C30—C31 | 1.389 (2) |
C7—H7 | 0.9500 | C31—C32 | 1.396 (2) |
C7—C8 | 1.3930 (18) | C31—C34 | 1.5036 (19) |
C8—H8 | 0.9500 | C32—H32 | 0.9500 |
C8—C9 | 1.3957 (17) | C32—C33 | 1.3915 (18) |
C9—C10 | 1.4511 (16) | C33—H33 | 0.9500 |
C10—C11 | 1.4040 (16) | C34—H34A | 0.9800 |
C11—C12 | 1.4151 (17) | C34—H34B | 0.9800 |
C11—C35 | 1.4733 (17) | C34—H34C | 0.9800 |
C12—H12 | 0.9500 | C35—C36 | 1.3976 (18) |
C12—C13 | 1.3992 (17) | C35—C40 | 1.3993 (17) |
C13—C28 | 1.4702 (17) | C36—H36 | 0.9500 |
C14—C15 | 1.4020 (19) | C36—C37 | 1.3912 (18) |
C14—C19 | 1.3976 (19) | C37—H37 | 0.9500 |
C15—H15 | 0.9500 | C37—C38 | 1.396 (2) |
C15—C16 | 1.3907 (19) | C38—C39 | 1.388 (2) |
C16—H16 | 0.9500 | C38—C41 | 1.509 (2) |
C16—C17 | 1.393 (2) | C39—H39 | 0.9500 |
C17—C18 | 1.390 (2) | C39—C40 | 1.3945 (19) |
C17—C20 | 1.509 (2) | C40—H40 | 0.9500 |
C18—H18 | 0.9500 | C41—H41A | 0.9800 |
C18—C19 | 1.3929 (19) | C41—H41B | 0.9800 |
C19—H19 | 0.9500 | C41—H41C | 0.9800 |
N1—Ni—N3 | 163.95 (5) | C17—C20—H20A | 109.5 |
N1—Ni—N4 | 96.98 (5) | C17—C20—H20B | 109.5 |
N2—Ni—N1 | 83.41 (4) | C17—C20—H20C | 109.5 |
N2—Ni—N3 | 82.95 (4) | H20A—C20—H20B | 109.5 |
N2—Ni—N4 | 162.16 (5) | H20A—C20—H20C | 109.5 |
N3—Ni—N4 | 98.59 (5) | H20B—C20—H20C | 109.5 |
C1—N1—Ni | 140.10 (9) | C22—C21—C3 | 120.99 (12) |
C1—N1—C4 | 106.75 (10) | C22—C21—C26 | 117.86 (12) |
C4—N1—Ni | 113.07 (8) | C26—C21—C3 | 121.15 (12) |
C5—N2—Ni | 117.40 (8) | C21—C22—H22 | 119.6 |
C5—N2—C9 | 123.28 (11) | C21—C22—C23 | 120.86 (13) |
C9—N2—Ni | 118.43 (8) | C23—C22—H22 | 119.6 |
C10—N3—Ni | 114.29 (8) | C22—C23—H23 | 119.4 |
C13—N3—Ni | 138.51 (9) | C24—C23—C22 | 121.30 (13) |
C13—N3—C10 | 107.19 (10) | C24—C23—H23 | 119.4 |
Ni—N4—H4A | 113.0 (16) | C23—C24—C27 | 121.29 (13) |
Ni—N4—H4B | 120.3 (18) | C25—C24—C23 | 117.64 (12) |
Ni—N4—H4C | 106.2 (16) | C25—C24—C27 | 121.07 (13) |
H4A—N4—H4B | 103 (2) | C24—C25—H25 | 119.3 |
H4A—N4—H4C | 111 (2) | C24—C25—C26 | 121.37 (13) |
H4B—N4—H4C | 103 (2) | C26—C25—H25 | 119.3 |
N1—C1—C2 | 109.43 (11) | C21—C26—H26 | 119.5 |
N1—C1—C14 | 123.64 (11) | C25—C26—C21 | 120.91 (13) |
C2—C1—C14 | 126.55 (11) | C25—C26—H26 | 119.5 |
C1—C2—H2 | 126.1 | C24—C27—H27A | 109.5 |
C1—C2—C3 | 107.83 (11) | C24—C27—H27B | 109.5 |
C3—C2—H2 | 126.1 | C24—C27—H27C | 109.5 |
C2—C3—C21 | 127.47 (11) | H27A—C27—H27B | 109.5 |
C4—C3—C2 | 105.55 (11) | H27A—C27—H27C | 109.5 |
C4—C3—C21 | 126.95 (11) | H27B—C27—H27C | 109.5 |
N1—C4—C3 | 110.43 (11) | C29—C28—C13 | 119.81 (12) |
N1—C4—C5 | 113.98 (10) | C29—C28—C33 | 118.31 (12) |
C3—C4—C5 | 135.45 (11) | C33—C28—C13 | 121.79 (11) |
N2—C5—C4 | 110.79 (11) | C28—C29—H29 | 119.7 |
N2—C5—C6 | 119.41 (11) | C30—C29—C28 | 120.60 (13) |
C6—C5—C4 | 129.80 (11) | C30—C29—H29 | 119.7 |
C5—C6—H6 | 120.9 | C29—C30—H30 | 119.4 |
C7—C6—C5 | 118.23 (11) | C31—C30—C29 | 121.17 (13) |
C7—C6—H6 | 120.9 | C31—C30—H30 | 119.4 |
C6—C7—H7 | 119.3 | C30—C31—C32 | 118.41 (12) |
C6—C7—C8 | 121.36 (12) | C30—C31—C34 | 120.24 (14) |
C8—C7—H7 | 119.3 | C32—C31—C34 | 121.35 (15) |
C7—C8—H8 | 120.6 | C31—C32—H32 | 119.6 |
C7—C8—C9 | 118.76 (12) | C33—C32—C31 | 120.78 (13) |
C9—C8—H8 | 120.6 | C33—C32—H32 | 119.6 |
N2—C9—C8 | 118.92 (11) | C28—C33—H33 | 119.7 |
N2—C9—C10 | 110.48 (10) | C32—C33—C28 | 120.69 (12) |
C8—C9—C10 | 130.58 (11) | C32—C33—H33 | 119.7 |
N3—C10—C9 | 113.09 (10) | C31—C34—H34A | 109.5 |
N3—C10—C11 | 109.98 (10) | C31—C34—H34B | 109.5 |
C11—C10—C9 | 136.93 (11) | C31—C34—H34C | 109.5 |
C10—C11—C12 | 105.46 (11) | H34A—C34—H34B | 109.5 |
C10—C11—C35 | 130.14 (11) | H34A—C34—H34C | 109.5 |
C12—C11—C35 | 124.37 (11) | H34B—C34—H34C | 109.5 |
C11—C12—H12 | 126.1 | C36—C35—C11 | 121.84 (11) |
C13—C12—C11 | 107.90 (11) | C36—C35—C40 | 117.73 (12) |
C13—C12—H12 | 126.1 | C40—C35—C11 | 120.38 (12) |
N3—C13—C12 | 109.47 (11) | C35—C36—H36 | 119.4 |
N3—C13—C28 | 123.82 (11) | C37—C36—C35 | 121.14 (12) |
C12—C13—C28 | 126.61 (11) | C37—C36—H36 | 119.4 |
C15—C14—C1 | 121.12 (12) | C36—C37—H37 | 119.5 |
C19—C14—C1 | 120.80 (12) | C36—C37—C38 | 121.07 (13) |
C19—C14—C15 | 117.94 (12) | C38—C37—H37 | 119.5 |
C14—C15—H15 | 119.6 | C37—C38—C41 | 120.51 (14) |
C16—C15—C14 | 120.76 (13) | C39—C38—C37 | 117.85 (13) |
C16—C15—H15 | 119.6 | C39—C38—C41 | 121.63 (14) |
C15—C16—H16 | 119.4 | C38—C39—H39 | 119.3 |
C15—C16—C17 | 121.11 (14) | C38—C39—C40 | 121.48 (13) |
C17—C16—H16 | 119.4 | C40—C39—H39 | 119.3 |
C16—C17—C20 | 120.48 (15) | C35—C40—H40 | 119.6 |
C18—C17—C16 | 118.22 (13) | C39—C40—C35 | 120.72 (13) |
C18—C17—C20 | 121.26 (15) | C39—C40—H40 | 119.6 |
C17—C18—H18 | 119.5 | C38—C41—H41A | 109.5 |
C17—C18—C19 | 121.09 (14) | C38—C41—H41B | 109.5 |
C19—C18—H18 | 119.5 | C38—C41—H41C | 109.5 |
C14—C19—H19 | 119.6 | H41A—C41—H41B | 109.5 |
C18—C19—C14 | 120.85 (14) | H41A—C41—H41C | 109.5 |
C18—C19—H19 | 119.6 | H41B—C41—H41C | 109.5 |
Ni—N1—C1—C2 | −175.37 (11) | C5—N2—C9—C10 | −178.59 (11) |
Ni—N1—C1—C14 | 11.3 (2) | C5—C6—C7—C8 | −0.50 (19) |
Ni—N1—C4—C3 | 176.50 (9) | C6—C7—C8—C9 | −1.2 (2) |
Ni—N1—C4—C5 | −7.17 (14) | C7—C8—C9—N2 | 1.34 (18) |
Ni—N2—C5—C4 | 9.41 (13) | C7—C8—C9—C10 | 179.84 (13) |
Ni—N2—C5—C6 | −170.85 (9) | C8—C9—C10—N3 | −172.66 (13) |
Ni—N2—C9—C8 | 169.03 (9) | C8—C9—C10—C11 | 7.1 (3) |
Ni—N2—C9—C10 | −9.75 (14) | C9—N2—C5—C4 | 178.36 (11) |
Ni—N3—C10—C9 | −0.02 (13) | C9—N2—C5—C6 | −1.90 (18) |
Ni—N3—C10—C11 | −179.83 (8) | C9—C10—C11—C12 | −179.68 (14) |
Ni—N3—C13—C12 | 179.52 (10) | C9—C10—C11—C35 | 2.3 (2) |
Ni—N3—C13—C28 | −4.1 (2) | C10—N3—C13—C12 | −1.25 (14) |
N1—Ni—N2—C5 | −10.93 (9) | C10—N3—C13—C28 | 175.14 (11) |
N1—Ni—N2—C9 | 179.57 (10) | C10—C11—C12—C13 | −0.82 (14) |
N1—Ni—N3—C10 | −36.0 (2) | C10—C11—C35—C36 | 41.5 (2) |
N1—Ni—N3—C13 | 143.17 (16) | C10—C11—C35—C40 | −141.21 (14) |
N1—C1—C2—C3 | −0.70 (16) | C11—C12—C13—N3 | 1.30 (15) |
N1—C1—C14—C15 | 40.6 (2) | C11—C12—C13—C28 | −174.95 (12) |
N1—C1—C14—C19 | −143.73 (13) | C11—C35—C36—C37 | 177.93 (12) |
N1—C4—C5—N2 | −1.13 (15) | C11—C35—C40—C39 | −178.08 (13) |
N1—C4—C5—C6 | 179.17 (12) | C12—C11—C35—C36 | −136.15 (14) |
N2—Ni—N1—C1 | −174.10 (15) | C12—C11—C35—C40 | 41.12 (19) |
N2—Ni—N1—C4 | 9.65 (9) | C12—C13—C28—C29 | −47.47 (19) |
N2—Ni—N3—C10 | −4.08 (9) | C12—C13—C28—C33 | 129.04 (14) |
N2—Ni—N3—C13 | 175.12 (14) | C13—N3—C10—C9 | −179.46 (10) |
N2—C5—C6—C7 | 2.00 (18) | C13—N3—C10—C11 | 0.73 (14) |
N2—C9—C10—N3 | 5.93 (15) | C13—C28—C29—C30 | 176.54 (12) |
N2—C9—C10—C11 | −174.33 (14) | C13—C28—C33—C32 | −177.98 (12) |
N3—Ni—N1—C1 | −142.19 (16) | C14—C1—C2—C3 | 172.34 (13) |
N3—Ni—N1—C4 | 41.6 (2) | C14—C15—C16—C17 | −1.9 (2) |
N3—Ni—N2—C5 | 177.54 (10) | C15—C14—C19—C18 | 0.7 (2) |
N3—Ni—N2—C9 | 8.03 (9) | C15—C16—C17—C18 | 2.0 (2) |
N3—C10—C11—C12 | 0.07 (14) | C15—C16—C17—C20 | −175.81 (14) |
N3—C10—C11—C35 | −177.94 (12) | C16—C17—C18—C19 | −0.8 (2) |
N3—C13—C28—C29 | 136.78 (13) | C17—C18—C19—C14 | −0.5 (2) |
N3—C13—C28—C33 | −46.72 (18) | C19—C14—C15—C16 | 0.5 (2) |
N4—Ni—N1—C1 | 23.86 (15) | C20—C17—C18—C19 | 176.98 (14) |
N4—Ni—N1—C4 | −152.39 (9) | C21—C3—C4—N1 | 178.67 (12) |
N4—Ni—N2—C5 | 81.38 (18) | C21—C3—C4—C5 | 3.5 (3) |
N4—Ni—N2—C9 | −88.12 (18) | C21—C22—C23—C24 | 0.0 (3) |
N4—Ni—N3—C10 | 157.98 (9) | C22—C21—C26—C25 | 1.7 (2) |
N4—Ni—N3—C13 | −22.82 (14) | C22—C23—C24—C25 | 2.0 (2) |
C1—N1—C4—C3 | −0.98 (15) | C22—C23—C24—C27 | −178.30 (17) |
C1—N1—C4—C5 | 175.35 (11) | C23—C24—C25—C26 | −2.2 (2) |
C1—C2—C3—C4 | 0.08 (16) | C24—C25—C26—C21 | 0.4 (2) |
C1—C2—C3—C21 | −178.02 (13) | C26—C21—C22—C23 | −1.9 (2) |
C1—C14—C15—C16 | 176.31 (13) | C27—C24—C25—C26 | 178.10 (16) |
C1—C14—C19—C18 | −175.15 (13) | C28—C29—C30—C31 | 1.4 (2) |
C2—C1—C14—C15 | −131.52 (15) | C29—C28—C33—C32 | −1.42 (19) |
C2—C1—C14—C19 | 44.2 (2) | C29—C30—C31—C32 | −1.3 (2) |
C2—C3—C4—N1 | 0.55 (15) | C29—C30—C31—C34 | 179.26 (13) |
C2—C3—C4—C5 | −174.66 (15) | C30—C31—C32—C33 | −0.3 (2) |
C2—C3—C21—C22 | 73.9 (2) | C31—C32—C33—C28 | 1.6 (2) |
C2—C3—C21—C26 | −105.63 (17) | C33—C28—C29—C30 | −0.08 (19) |
C3—C4—C5—N2 | 173.97 (14) | C34—C31—C32—C33 | 179.22 (13) |
C3—C4—C5—C6 | −5.7 (3) | C35—C11—C12—C13 | 177.34 (12) |
C3—C21—C22—C23 | 178.53 (14) | C35—C36—C37—C38 | 0.2 (2) |
C3—C21—C26—C25 | −178.73 (13) | C36—C35—C40—C39 | −0.7 (2) |
C4—N1—C1—C2 | 1.02 (15) | C36—C37—C38—C39 | −0.8 (2) |
C4—N1—C1—C14 | −172.26 (12) | C36—C37—C38—C41 | 179.97 (14) |
C4—C3—C21—C22 | −103.77 (17) | C37—C38—C39—C40 | 0.7 (2) |
C4—C3—C21—C26 | 76.66 (19) | C38—C39—C40—C35 | 0.1 (2) |
C4—C5—C6—C7 | −178.31 (13) | C40—C35—C36—C37 | 0.6 (2) |
C5—N2—C9—C8 | 0.19 (18) | C41—C38—C39—C40 | 179.91 (14) |
[Ni(C41H33N3)(C2H3N)] | Z = 2 |
Mr = 753.64 | F(000) = 800 |
Triclinic, P1 | Dx = 1.240 Mg m−3 |
a = 11.2735 (16) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 14.1802 (19) Å | Cell parameters from 8799 reflections |
c = 14.688 (2) Å | θ = 2.5–32.8° |
α = 67.162 (2)° | µ = 0.52 mm−1 |
β = 68.881 (2)° | T = 100 K |
γ = 80.665 (2)° | Prism, colourless |
V = 2018.0 (5) Å3 | 0.20 × 0.12 × 0.09 mm |
Bruker APEXII CCD diffractometer | 7327 reflections with I > 2σ(I) |
Curved-graphite monochromator | Rint = 0.058 |
φ and ω scans | θmax = 28.3°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −15→15 |
Tmin = 0.686, Tmax = 0.899 | k = −18→18 |
21869 measured reflections | l = −19→19 |
9994 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.068 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.193 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.1214P)2] where P = (Fo2 + 2Fc2)/3 |
9994 reflections | (Δ/σ)max = 0.002 |
551 parameters | Δρmax = 1.75 e Å−3 |
178 restraints | Δρmin = −0.93 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 | Occ. (<1) | |
Ni | 0.71466 (3) | 1.00913 (3) | 0.03328 (2) | 0.02033 (13) | |
N1 | 0.7942 (2) | 1.03447 (17) | −0.11157 (17) | 0.0212 (5) | |
N2 | 0.6207 (2) | 0.91916 (17) | 0.02538 (17) | 0.0210 (5) | |
N3 | 0.6076 (2) | 0.96688 (17) | 0.17567 (17) | 0.0224 (5) | |
N4 | 0.8317 (2) | 1.07621 (18) | 0.04797 (16) | 0.0229 (5) | |
C1 | 0.9005 (2) | 1.0819 (2) | −0.19073 (19) | 0.0223 (5) | |
C2 | 0.9285 (3) | 1.0467 (2) | −0.2735 (2) | 0.0247 (6) | |
H2 | 0.998662 | 1.066023 | −0.336441 | 0.030* | |
C3 | 0.8342 (3) | 0.9777 (2) | −0.2468 (2) | 0.0226 (5) | |
C4 | 0.7529 (3) | 0.9711 (2) | −0.1464 (2) | 0.0222 (5) | |
C5 | 0.9676 (3) | 1.1629 (2) | −0.19148 (19) | 0.0226 (5) | |
C6 | 0.9035 (3) | 1.2478 (2) | −0.1678 (2) | 0.0276 (6) | |
H6 | 0.813506 | 1.253780 | −0.150189 | 0.033* | |
C7 | 0.9693 (3) | 1.3232 (2) | −0.1696 (2) | 0.0333 (7) | |
H7 | 0.923784 | 1.379786 | −0.152441 | 0.040* | |
C8 | 1.1014 (3) | 1.3173 (2) | −0.1963 (2) | 0.0343 (7) | |
C9 | 1.1657 (3) | 1.2342 (2) | −0.2225 (2) | 0.0311 (7) | |
H9 | 1.255844 | 1.229402 | −0.242326 | 0.037* | |
C10 | 1.0997 (3) | 1.1583 (2) | −0.2200 (2) | 0.0266 (6) | |
H10 | 1.145525 | 1.102123 | −0.238019 | 0.032* | |
C11 | 1.1735 (4) | 1.3984 (3) | −0.1962 (3) | 0.0535 (10) | |
H11A | 1.217241 | 1.441655 | −0.268374 | 0.080* | |
H11B | 1.236159 | 1.365374 | −0.160591 | 0.080* | |
H11C | 1.113791 | 1.440597 | −0.159493 | 0.080* | |
C12 | 0.8259 (3) | 0.9241 (2) | −0.31327 (19) | 0.0241 (6) | |
C13 | 0.9345 (3) | 0.8812 (2) | −0.3679 (2) | 0.0290 (6) | |
H13 | 1.014827 | 0.888036 | −0.364089 | 0.035* | |
C14 | 0.9268 (3) | 0.8288 (2) | −0.4276 (2) | 0.0332 (7) | |
H14 | 1.002180 | 0.800355 | −0.464251 | 0.040* | |
C15 | 0.8110 (3) | 0.8167 (2) | −0.4353 (2) | 0.0298 (6) | |
C16 | 0.7029 (3) | 0.8629 (2) | −0.3836 (2) | 0.0296 (6) | |
H16 | 0.622987 | 0.857461 | −0.389079 | 0.036* | |
C17 | 0.7102 (3) | 0.9167 (2) | −0.3242 (2) | 0.0273 (6) | |
H17 | 0.635718 | 0.948668 | −0.290877 | 0.033* | |
C18 | 0.8019 (4) | 0.7559 (3) | −0.4967 (3) | 0.0419 (8) | |
H18A | 0.783106 | 0.684718 | −0.450295 | 0.063* | |
H18B | 0.882819 | 0.758244 | −0.552870 | 0.063* | |
H18C | 0.733704 | 0.785281 | −0.527028 | 0.063* | |
C19 | 0.6536 (3) | 0.9030 (2) | −0.0665 (2) | 0.0229 (6) | |
C20 | 0.5975 (3) | 0.8240 (2) | −0.0690 (2) | 0.0272 (6) | |
H20 | 0.618319 | 0.811856 | −0.132312 | 0.033* | |
C21 | 0.5111 (3) | 0.7634 (2) | 0.0217 (2) | 0.0296 (6) | |
H21 | 0.471606 | 0.710148 | 0.019940 | 0.035* | |
C22 | 0.4807 (3) | 0.7788 (2) | 0.1153 (2) | 0.0278 (6) | |
H22 | 0.421338 | 0.736637 | 0.177326 | 0.033* | |
C23 | 0.5394 (2) | 0.8577 (2) | 0.1162 (2) | 0.0220 (5) | |
C24 | 0.5332 (3) | 0.8847 (2) | 0.2030 (2) | 0.0222 (5) | |
C25 | 0.4838 (3) | 0.8383 (2) | 0.3115 (2) | 0.0231 (6) | |
C26 | 0.5283 (3) | 0.8943 (2) | 0.3523 (2) | 0.0244 (6) | |
H26 | 0.511937 | 0.880844 | 0.424332 | 0.029* | |
C27 | 0.6013 (3) | 0.9739 (2) | 0.2682 (2) | 0.0223 (5) | |
C28 | 0.3986 (3) | 0.7499 (2) | 0.3716 (2) | 0.0224 (5) | |
C29 | 0.2832 (3) | 0.7518 (2) | 0.3561 (2) | 0.0275 (6) | |
H29 | 0.258054 | 0.811361 | 0.307600 | 0.033* | |
C30 | 0.2044 (3) | 0.6683 (2) | 0.4102 (2) | 0.0280 (6) | |
H30 | 0.126830 | 0.671260 | 0.397359 | 0.034* | |
C31 | 0.2374 (3) | 0.5802 (2) | 0.4830 (2) | 0.0290 (6) | |
C32 | 0.3523 (3) | 0.5792 (2) | 0.4990 (2) | 0.0331 (7) | |
H32 | 0.376789 | 0.520100 | 0.548445 | 0.040* | |
C33 | 0.4316 (3) | 0.6622 (2) | 0.4446 (2) | 0.0290 (6) | |
H33 | 0.509344 | 0.659241 | 0.457219 | 0.035* | |
C34 | 0.1504 (3) | 0.4896 (3) | 0.5423 (3) | 0.0412 (8) | |
H34A | 0.198295 | 0.428387 | 0.572026 | 0.062* | |
H34B | 0.116748 | 0.478387 | 0.494491 | 0.062* | |
H34C | 0.079749 | 0.503573 | 0.598715 | 0.062* | |
C35 | 0.6484 (3) | 1.0604 (2) | 0.2766 (2) | 0.0263 (6) | |
C36 | 0.6888 (3) | 1.0435 (3) | 0.3615 (2) | 0.0336 (7) | |
H36 | 0.689473 | 0.976019 | 0.410764 | 0.040* | |
C37 | 0.7279 (3) | 1.1237 (3) | 0.3746 (3) | 0.0408 (8) | |
H37 | 0.752837 | 1.110883 | 0.433680 | 0.049* | |
C38 | 0.7310 (3) | 1.2221 (3) | 0.3028 (3) | 0.0434 (9) | |
C39 | 0.6875 (3) | 1.2401 (3) | 0.2198 (3) | 0.0410 (8) | |
H39 | 0.686475 | 1.307769 | 0.171157 | 0.049* | |
C40 | 0.6455 (3) | 1.1603 (2) | 0.2071 (2) | 0.0306 (6) | |
H40 | 0.614683 | 1.174097 | 0.150804 | 0.037* | |
C41 | 0.7823 (4) | 1.3079 (4) | 0.3137 (4) | 0.0701 (14) | |
H41A | 0.772811 | 1.291198 | 0.387242 | 0.105* | |
H41B | 0.734805 | 1.371589 | 0.289428 | 0.105* | |
H41C | 0.872489 | 1.316474 | 0.271541 | 0.105* | |
C42 | 0.9054 (3) | 1.1128 (2) | 0.0596 (2) | 0.0229 (6) | |
C43 | 0.9938 (3) | 1.1640 (2) | 0.0752 (2) | 0.0301 (6) | |
H43A | 0.962221 | 1.233843 | 0.069903 | 0.045* | |
H43B | 1.077168 | 1.166375 | 0.021547 | 0.045* | |
H43C | 1.001893 | 1.126315 | 0.144527 | 0.045* | |
C1A | 0.5344 (10) | 0.5285 (8) | −0.2757 (10) | 0.090 (3) | 0.779 (5) |
H1AA | 0.557765 | 0.492990 | −0.325469 | 0.136* | 0.779 (5) |
H1AB | 0.524481 | 0.602094 | −0.312423 | 0.136* | 0.779 (5) |
H1AC | 0.453946 | 0.502305 | −0.220821 | 0.136* | 0.779 (5) |
C1B | 0.6389 (7) | 0.5100 (5) | −0.2266 (5) | 0.0786 (19) | 0.779 (5) |
H1BA | 0.648783 | 0.435829 | −0.188773 | 0.094* | 0.779 (5) |
H1BB | 0.720963 | 0.534607 | −0.281865 | 0.094* | 0.779 (5) |
C1C | 0.6032 (7) | 0.5668 (6) | −0.1514 (6) | 0.0899 (19) | 0.779 (5) |
H1CA | 0.594961 | 0.640780 | −0.190716 | 0.108* | 0.779 (5) |
H1CB | 0.518935 | 0.543845 | −0.098965 | 0.108* | 0.779 (5) |
C1D | 0.6971 (6) | 0.5521 (5) | −0.0944 (5) | 0.0818 (18) | 0.779 (5) |
H1DA | 0.715769 | 0.477924 | −0.064400 | 0.098* | 0.779 (5) |
H1DB | 0.656402 | 0.576885 | −0.035486 | 0.098* | 0.779 (5) |
C1E | 0.8225 (6) | 0.6066 (5) | −0.1616 (5) | 0.0698 (17) | 0.779 (5) |
H1EA | 0.806894 | 0.679286 | −0.200932 | 0.084* | 0.779 (5) |
H1EB | 0.874385 | 0.573326 | −0.211928 | 0.084* | 0.779 (5) |
C1F | 0.8895 (11) | 0.5976 (8) | −0.0849 (8) | 0.114 (3) | 0.779 (5) |
H1FA | 0.976978 | 0.620915 | −0.123713 | 0.170* | 0.779 (5) |
H1FB | 0.890856 | 0.526034 | −0.038434 | 0.170* | 0.779 (5) |
H1FC | 0.843881 | 0.640080 | −0.043258 | 0.170* | 0.779 (5) |
C1G | 0.519 (4) | 0.501 (2) | −0.269 (3) | 0.063 (5) | 0.221 (5) |
H1GA | 0.508682 | 0.549644 | −0.335107 | 0.095* | 0.221 (5) |
H1GB | 0.438516 | 0.466834 | −0.223634 | 0.095* | 0.221 (5) |
H1GC | 0.585205 | 0.449655 | −0.284042 | 0.095* | 0.221 (5) |
C1H | 0.5578 (19) | 0.558 (2) | −0.215 (2) | 0.084 (4) | 0.221 (5) |
H1HA | 0.504530 | 0.534871 | −0.140764 | 0.100* | 0.221 (5) |
H1HB | 0.539431 | 0.632029 | −0.246983 | 0.100* | 0.221 (5) |
C1I | 0.6978 (19) | 0.543 (2) | −0.222 (2) | 0.085 (4) | 0.221 (5) |
H1IA | 0.715850 | 0.469931 | −0.187097 | 0.102* | 0.221 (5) |
H1IB | 0.751851 | 0.563699 | −0.296523 | 0.102* | 0.221 (5) |
C1J | 0.732 (2) | 0.6058 (17) | −0.172 (2) | 0.090 (4) | 0.221 (5) |
H1JA | 0.651340 | 0.636442 | −0.137639 | 0.108* | 0.221 (5) |
H1JB | 0.783165 | 0.663231 | −0.229621 | 0.108* | 0.221 (5) |
C1K | 0.802 (3) | 0.5613 (16) | −0.092 (2) | 0.094 (4) | 0.221 (5) |
H1KA | 0.856979 | 0.501915 | −0.103297 | 0.113* | 0.221 (5) |
H1KB | 0.741166 | 0.538388 | −0.020175 | 0.113* | 0.221 (5) |
C1L | 0.884 (4) | 0.647 (2) | −0.108 (3) | 0.078 (5) | 0.221 (5) |
H1LA | 0.941234 | 0.670951 | −0.180777 | 0.116* | 0.221 (5) |
H1LB | 0.934141 | 0.620361 | −0.060830 | 0.116* | 0.221 (5) |
H1LC | 0.828534 | 0.703624 | −0.093759 | 0.116* | 0.221 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni | 0.0217 (2) | 0.0251 (2) | 0.01235 (18) | −0.00525 (13) | −0.00082 (13) | −0.00728 (14) |
N1 | 0.0227 (11) | 0.0236 (11) | 0.0153 (10) | −0.0031 (9) | −0.0035 (9) | −0.0066 (9) |
N2 | 0.0209 (11) | 0.0276 (12) | 0.0133 (10) | −0.0047 (9) | −0.0018 (8) | −0.0079 (9) |
N3 | 0.0225 (11) | 0.0271 (12) | 0.0163 (10) | −0.0034 (9) | −0.0016 (9) | −0.0095 (9) |
N4 | 0.0243 (11) | 0.0282 (12) | 0.0111 (10) | −0.0064 (9) | 0.0010 (8) | −0.0058 (9) |
C1 | 0.0210 (13) | 0.0272 (14) | 0.0125 (11) | −0.0021 (11) | −0.0009 (10) | −0.0043 (10) |
C2 | 0.0250 (13) | 0.0289 (14) | 0.0151 (12) | −0.0008 (11) | −0.0017 (10) | −0.0070 (11) |
C3 | 0.0247 (13) | 0.0273 (14) | 0.0135 (12) | 0.0010 (11) | −0.0042 (10) | −0.0075 (10) |
C4 | 0.0250 (13) | 0.0261 (14) | 0.0148 (12) | −0.0011 (11) | −0.0054 (10) | −0.0075 (10) |
C5 | 0.0245 (13) | 0.0260 (13) | 0.0115 (11) | −0.0038 (11) | −0.0018 (10) | −0.0030 (10) |
C6 | 0.0301 (15) | 0.0299 (15) | 0.0190 (13) | −0.0029 (12) | −0.0058 (11) | −0.0060 (11) |
C7 | 0.0455 (18) | 0.0264 (15) | 0.0245 (15) | −0.0033 (13) | −0.0066 (13) | −0.0090 (12) |
C8 | 0.0450 (18) | 0.0346 (16) | 0.0188 (14) | −0.0156 (14) | −0.0057 (13) | −0.0036 (12) |
C9 | 0.0283 (15) | 0.0400 (17) | 0.0195 (13) | −0.0083 (13) | −0.0047 (11) | −0.0050 (12) |
C10 | 0.0281 (14) | 0.0294 (15) | 0.0156 (12) | −0.0033 (11) | −0.0024 (11) | −0.0047 (11) |
C11 | 0.065 (3) | 0.053 (2) | 0.045 (2) | −0.028 (2) | −0.0103 (19) | −0.0168 (18) |
C12 | 0.0298 (14) | 0.0270 (14) | 0.0106 (11) | −0.0032 (11) | −0.0002 (10) | −0.0066 (10) |
C13 | 0.0274 (14) | 0.0364 (16) | 0.0198 (13) | −0.0018 (12) | −0.0016 (11) | −0.0119 (12) |
C14 | 0.0363 (17) | 0.0378 (17) | 0.0204 (14) | 0.0005 (13) | 0.0010 (12) | −0.0153 (13) |
C15 | 0.0395 (17) | 0.0325 (15) | 0.0142 (12) | −0.0067 (13) | −0.0008 (11) | −0.0100 (11) |
C16 | 0.0325 (15) | 0.0398 (16) | 0.0179 (13) | −0.0049 (13) | −0.0063 (11) | −0.0120 (12) |
C17 | 0.0304 (15) | 0.0353 (15) | 0.0142 (12) | 0.0002 (12) | −0.0030 (11) | −0.0111 (11) |
C18 | 0.055 (2) | 0.0460 (19) | 0.0255 (16) | −0.0127 (16) | −0.0008 (15) | −0.0210 (15) |
C19 | 0.0243 (13) | 0.0290 (14) | 0.0132 (12) | 0.0002 (11) | −0.0030 (10) | −0.0085 (10) |
C20 | 0.0299 (15) | 0.0353 (15) | 0.0169 (13) | −0.0067 (12) | −0.0039 (11) | −0.0110 (12) |
C21 | 0.0316 (15) | 0.0347 (16) | 0.0232 (14) | −0.0116 (12) | −0.0042 (12) | −0.0114 (12) |
C22 | 0.0270 (14) | 0.0328 (15) | 0.0189 (13) | −0.0110 (12) | 0.0000 (11) | −0.0073 (12) |
C23 | 0.0208 (13) | 0.0268 (13) | 0.0137 (12) | −0.0027 (10) | −0.0004 (10) | −0.0065 (10) |
C24 | 0.0217 (13) | 0.0260 (13) | 0.0165 (12) | −0.0038 (10) | −0.0019 (10) | −0.0079 (10) |
C25 | 0.0204 (13) | 0.0289 (14) | 0.0165 (12) | −0.0021 (11) | −0.0014 (10) | −0.0081 (11) |
C26 | 0.0238 (13) | 0.0330 (15) | 0.0148 (12) | −0.0027 (11) | −0.0016 (10) | −0.0105 (11) |
C27 | 0.0222 (13) | 0.0282 (14) | 0.0146 (12) | −0.0020 (11) | −0.0024 (10) | −0.0085 (10) |
C28 | 0.0241 (13) | 0.0243 (13) | 0.0144 (12) | −0.0039 (11) | 0.0001 (10) | −0.0069 (10) |
C29 | 0.0290 (14) | 0.0274 (14) | 0.0186 (13) | −0.0016 (11) | −0.0043 (11) | −0.0033 (11) |
C30 | 0.0250 (14) | 0.0346 (15) | 0.0223 (14) | −0.0048 (12) | −0.0035 (11) | −0.0104 (12) |
C31 | 0.0340 (16) | 0.0301 (15) | 0.0202 (13) | −0.0075 (12) | −0.0019 (12) | −0.0101 (12) |
C32 | 0.0402 (17) | 0.0275 (15) | 0.0252 (15) | −0.0031 (13) | −0.0100 (13) | −0.0024 (12) |
C33 | 0.0275 (14) | 0.0333 (15) | 0.0241 (14) | −0.0036 (12) | −0.0077 (12) | −0.0074 (12) |
C34 | 0.045 (2) | 0.0354 (17) | 0.0371 (18) | −0.0169 (15) | −0.0078 (15) | −0.0053 (14) |
C35 | 0.0221 (13) | 0.0374 (16) | 0.0189 (13) | −0.0037 (12) | 0.0020 (10) | −0.0164 (12) |
C36 | 0.0269 (15) | 0.054 (2) | 0.0222 (14) | −0.0069 (14) | 0.0008 (11) | −0.0220 (14) |
C37 | 0.0291 (16) | 0.066 (2) | 0.0367 (18) | −0.0086 (15) | −0.0001 (13) | −0.0357 (18) |
C38 | 0.0357 (18) | 0.055 (2) | 0.047 (2) | −0.0112 (15) | 0.0054 (15) | −0.0389 (18) |
C39 | 0.0355 (17) | 0.0375 (18) | 0.046 (2) | −0.0045 (14) | 0.0027 (15) | −0.0235 (16) |
C40 | 0.0254 (14) | 0.0332 (16) | 0.0290 (15) | −0.0041 (12) | 0.0008 (12) | −0.0145 (13) |
C41 | 0.064 (3) | 0.081 (3) | 0.084 (3) | −0.019 (2) | 0.000 (2) | −0.064 (3) |
C42 | 0.0268 (14) | 0.0238 (13) | 0.0143 (12) | −0.0032 (11) | −0.0034 (10) | −0.0049 (10) |
C43 | 0.0299 (15) | 0.0332 (16) | 0.0292 (15) | −0.0073 (12) | −0.0112 (12) | −0.0095 (13) |
C1A | 0.094 (6) | 0.093 (6) | 0.098 (5) | −0.016 (5) | −0.010 (5) | −0.061 (5) |
C1B | 0.092 (4) | 0.070 (4) | 0.068 (3) | −0.007 (3) | −0.014 (3) | −0.027 (3) |
C1C | 0.104 (4) | 0.080 (4) | 0.082 (4) | −0.008 (3) | −0.023 (3) | −0.030 (3) |
C1D | 0.087 (4) | 0.070 (3) | 0.082 (4) | −0.006 (3) | −0.020 (3) | −0.027 (3) |
C1E | 0.078 (4) | 0.059 (3) | 0.063 (3) | −0.012 (3) | −0.010 (3) | −0.020 (3) |
C1F | 0.121 (6) | 0.121 (7) | 0.107 (7) | −0.036 (7) | −0.012 (6) | −0.060 (6) |
C1G | 0.084 (10) | 0.062 (10) | 0.076 (9) | −0.002 (9) | −0.048 (8) | −0.038 (8) |
C1H | 0.098 (6) | 0.085 (6) | 0.076 (6) | −0.003 (6) | −0.026 (6) | −0.038 (5) |
C1I | 0.095 (5) | 0.080 (5) | 0.077 (5) | −0.008 (5) | −0.023 (5) | −0.028 (5) |
C1J | 0.094 (5) | 0.081 (5) | 0.079 (5) | −0.006 (5) | −0.017 (5) | −0.020 (5) |
C1K | 0.097 (6) | 0.084 (6) | 0.087 (6) | −0.008 (6) | −0.017 (6) | −0.025 (6) |
C1L | 0.097 (10) | 0.072 (11) | 0.078 (10) | −0.033 (10) | −0.028 (9) | −0.031 (9) |
Ni—N1 | 1.896 (2) | C30—C31 | 1.394 (4) |
Ni—N2 | 1.846 (2) | C31—C32 | 1.394 (4) |
Ni—N3 | 1.906 (2) | C31—C34 | 1.515 (4) |
Ni—N4 | 1.861 (2) | C32—H32 | 0.9500 |
N1—C1 | 1.375 (3) | C32—C33 | 1.386 (4) |
N1—C4 | 1.397 (3) | C33—H33 | 0.9500 |
N2—C19 | 1.365 (3) | C34—H34A | 0.9800 |
N2—C23 | 1.362 (3) | C34—H34B | 0.9800 |
N3—C24 | 1.390 (3) | C34—H34C | 0.9800 |
N3—C27 | 1.376 (3) | C35—C36 | 1.401 (4) |
N4—C42 | 1.140 (3) | C35—C40 | 1.391 (4) |
C1—C2 | 1.404 (4) | C36—H36 | 0.9500 |
C1—C5 | 1.469 (4) | C36—C37 | 1.385 (4) |
C2—H2 | 0.9500 | C37—H37 | 0.9500 |
C2—C3 | 1.407 (4) | C37—C38 | 1.381 (5) |
C3—C4 | 1.403 (4) | C38—C39 | 1.393 (5) |
C3—C12 | 1.485 (4) | C38—C41 | 1.512 (5) |
C4—C19 | 1.445 (4) | C39—H39 | 0.9500 |
C5—C6 | 1.398 (4) | C39—C40 | 1.393 (4) |
C5—C10 | 1.392 (4) | C40—H40 | 0.9500 |
C6—H6 | 0.9500 | C41—H41A | 0.9800 |
C6—C7 | 1.384 (4) | C41—H41B | 0.9800 |
C7—H7 | 0.9500 | C41—H41C | 0.9800 |
C7—C8 | 1.394 (5) | C42—C43 | 1.449 (4) |
C8—C9 | 1.391 (5) | C43—H43A | 0.9800 |
C8—C11 | 1.512 (4) | C43—H43B | 0.9800 |
C9—H9 | 0.9500 | C43—H43C | 0.9800 |
C9—C10 | 1.386 (4) | C1A—H1AA | 0.9800 |
C10—H10 | 0.9500 | C1A—H1AB | 0.9800 |
C11—H11A | 0.9800 | C1A—H1AC | 0.9800 |
C11—H11B | 0.9800 | C1A—C1B | 1.532 (6) |
C11—H11C | 0.9800 | C1B—H1BA | 0.9900 |
C12—C13 | 1.394 (4) | C1B—H1BB | 0.9900 |
C12—C17 | 1.395 (4) | C1B—C1C | 1.515 (5) |
C13—H13 | 0.9500 | C1C—H1CA | 0.9900 |
C13—C14 | 1.382 (4) | C1C—H1CB | 0.9900 |
C14—H14 | 0.9500 | C1C—C1D | 1.515 (5) |
C14—C15 | 1.393 (4) | C1D—H1DA | 0.9900 |
C15—C16 | 1.397 (4) | C1D—H1DB | 0.9900 |
C15—C18 | 1.506 (4) | C1D—C1E | 1.525 (5) |
C16—H16 | 0.9500 | C1E—H1EA | 0.9900 |
C16—C17 | 1.393 (4) | C1E—H1EB | 0.9900 |
C17—H17 | 0.9500 | C1E—C1F | 1.526 (5) |
C18—H18A | 0.9800 | C1F—H1FA | 0.9800 |
C18—H18B | 0.9800 | C1F—H1FB | 0.9800 |
C18—H18C | 0.9800 | C1F—H1FC | 0.9800 |
C19—C20 | 1.391 (4) | C1G—H1GA | 0.9800 |
C20—H20 | 0.9500 | C1G—H1GB | 0.9800 |
C20—C21 | 1.382 (4) | C1G—H1GC | 0.9800 |
C21—H21 | 0.9500 | C1G—C1H | 1.529 (6) |
C21—C22 | 1.387 (4) | C1H—H1HA | 0.9900 |
C22—H22 | 0.9500 | C1H—H1HB | 0.9900 |
C22—C23 | 1.395 (4) | C1H—C1I | 1.530 (6) |
C23—C24 | 1.443 (4) | C1I—H1IA | 0.9900 |
C24—C25 | 1.396 (4) | C1I—H1IB | 0.9900 |
C25—C26 | 1.399 (4) | C1I—C1J | 1.519 (6) |
C25—C28 | 1.481 (4) | C1J—H1JA | 0.9900 |
C26—H26 | 0.9500 | C1J—H1JB | 0.9900 |
C26—C27 | 1.401 (4) | C1J—C1K | 1.526 (6) |
C27—C35 | 1.476 (4) | C1K—H1KA | 0.9900 |
C28—C29 | 1.393 (4) | C1K—H1KB | 0.9900 |
C28—C33 | 1.392 (4) | C1K—C1L | 1.533 (6) |
C29—H29 | 0.9500 | C1L—H1LA | 0.9800 |
C29—C30 | 1.387 (4) | C1L—H1LB | 0.9800 |
C30—H30 | 0.9500 | C1L—H1LC | 0.9800 |
N1—Ni—N3 | 166.68 (9) | C31—C32—H32 | 119.2 |
N2—Ni—N1 | 83.38 (9) | C33—C32—C31 | 121.6 (3) |
N2—Ni—N3 | 83.52 (9) | C33—C32—H32 | 119.2 |
N2—Ni—N4 | 168.06 (10) | C28—C33—H33 | 119.7 |
N4—Ni—N1 | 96.77 (9) | C32—C33—C28 | 120.6 (3) |
N4—Ni—N3 | 96.54 (10) | C32—C33—H33 | 119.7 |
C1—N1—Ni | 138.26 (19) | C31—C34—H34A | 109.5 |
C1—N1—C4 | 106.5 (2) | C31—C34—H34B | 109.5 |
C4—N1—Ni | 113.43 (17) | C31—C34—H34C | 109.5 |
C19—N2—Ni | 118.35 (18) | H34A—C34—H34B | 109.5 |
C23—N2—Ni | 117.87 (18) | H34A—C34—H34C | 109.5 |
C23—N2—C19 | 122.5 (2) | H34B—C34—H34C | 109.5 |
C24—N3—Ni | 112.48 (17) | C36—C35—C27 | 119.3 (3) |
C27—N3—Ni | 138.85 (19) | C40—C35—C27 | 122.2 (3) |
C27—N3—C24 | 106.1 (2) | C40—C35—C36 | 118.3 (3) |
C42—N4—Ni | 176.7 (2) | C35—C36—H36 | 119.6 |
N1—C1—C2 | 109.5 (2) | C37—C36—C35 | 120.9 (3) |
N1—C1—C5 | 124.8 (2) | C37—C36—H36 | 119.6 |
C2—C1—C5 | 125.5 (2) | C36—C37—H37 | 119.6 |
C1—C2—H2 | 126.0 | C38—C37—C36 | 120.8 (3) |
C1—C2—C3 | 107.9 (2) | C38—C37—H37 | 119.6 |
C3—C2—H2 | 126.0 | C37—C38—C39 | 118.6 (3) |
C2—C3—C12 | 125.8 (2) | C37—C38—C41 | 120.4 (4) |
C4—C3—C2 | 105.8 (2) | C39—C38—C41 | 120.9 (4) |
C4—C3—C12 | 128.4 (3) | C38—C39—H39 | 119.5 |
N1—C4—C3 | 110.2 (2) | C38—C39—C40 | 121.0 (3) |
N1—C4—C19 | 113.8 (2) | C40—C39—H39 | 119.5 |
C3—C4—C19 | 134.9 (3) | C35—C40—C39 | 120.3 (3) |
C6—C5—C1 | 122.1 (2) | C35—C40—H40 | 119.9 |
C10—C5—C1 | 119.9 (3) | C39—C40—H40 | 119.9 |
C10—C5—C6 | 117.9 (3) | C38—C41—H41A | 109.5 |
C5—C6—H6 | 119.6 | C38—C41—H41B | 109.5 |
C7—C6—C5 | 120.8 (3) | C38—C41—H41C | 109.5 |
C7—C6—H6 | 119.6 | H41A—C41—H41B | 109.5 |
C6—C7—H7 | 119.5 | H41A—C41—H41C | 109.5 |
C6—C7—C8 | 121.1 (3) | H41B—C41—H41C | 109.5 |
C8—C7—H7 | 119.5 | N4—C42—C43 | 176.7 (3) |
C7—C8—C11 | 121.2 (3) | C42—C43—H43A | 109.5 |
C9—C8—C7 | 118.2 (3) | C42—C43—H43B | 109.5 |
C9—C8—C11 | 120.6 (3) | C42—C43—H43C | 109.5 |
C8—C9—H9 | 119.6 | H43A—C43—H43B | 109.5 |
C10—C9—C8 | 120.8 (3) | H43A—C43—H43C | 109.5 |
C10—C9—H9 | 119.6 | H43B—C43—H43C | 109.5 |
C5—C10—H10 | 119.4 | H1AA—C1A—H1AB | 109.5 |
C9—C10—C5 | 121.2 (3) | H1AA—C1A—H1AC | 109.5 |
C9—C10—H10 | 119.4 | H1AB—C1A—H1AC | 109.5 |
C8—C11—H11A | 109.5 | C1B—C1A—H1AA | 109.5 |
C8—C11—H11B | 109.5 | C1B—C1A—H1AB | 109.5 |
C8—C11—H11C | 109.5 | C1B—C1A—H1AC | 109.5 |
H11A—C11—H11B | 109.5 | C1A—C1B—H1BA | 109.9 |
H11A—C11—H11C | 109.5 | C1A—C1B—H1BB | 109.9 |
H11B—C11—H11C | 109.5 | H1BA—C1B—H1BB | 108.3 |
C13—C12—C3 | 120.6 (3) | C1C—C1B—C1A | 109.1 (7) |
C13—C12—C17 | 118.2 (3) | C1C—C1B—H1BA | 109.9 |
C17—C12—C3 | 121.2 (3) | C1C—C1B—H1BB | 109.9 |
C12—C13—H13 | 119.6 | C1B—C1C—H1CA | 108.6 |
C14—C13—C12 | 120.8 (3) | C1B—C1C—H1CB | 108.6 |
C14—C13—H13 | 119.6 | H1CA—C1C—H1CB | 107.6 |
C13—C14—H14 | 119.2 | C1D—C1C—C1B | 114.6 (6) |
C13—C14—C15 | 121.5 (3) | C1D—C1C—H1CA | 108.6 |
C15—C14—H14 | 119.2 | C1D—C1C—H1CB | 108.6 |
C14—C15—C16 | 117.6 (3) | C1C—C1D—H1DA | 108.5 |
C14—C15—C18 | 121.5 (3) | C1C—C1D—H1DB | 108.5 |
C16—C15—C18 | 120.9 (3) | C1C—C1D—C1E | 114.9 (6) |
C15—C16—H16 | 119.4 | H1DA—C1D—H1DB | 107.5 |
C17—C16—C15 | 121.1 (3) | C1E—C1D—H1DA | 108.5 |
C17—C16—H16 | 119.4 | C1E—C1D—H1DB | 108.5 |
C12—C17—H17 | 119.7 | C1D—C1E—H1EA | 110.7 |
C16—C17—C12 | 120.6 (3) | C1D—C1E—H1EB | 110.7 |
C16—C17—H17 | 119.7 | C1D—C1E—C1F | 105.3 (6) |
C15—C18—H18A | 109.5 | H1EA—C1E—H1EB | 108.8 |
C15—C18—H18B | 109.5 | C1F—C1E—H1EA | 110.7 |
C15—C18—H18C | 109.5 | C1F—C1E—H1EB | 110.7 |
H18A—C18—H18B | 109.5 | C1E—C1F—H1FA | 109.5 |
H18A—C18—H18C | 109.5 | C1E—C1F—H1FB | 109.5 |
H18B—C18—H18C | 109.5 | C1E—C1F—H1FC | 109.5 |
N2—C19—C4 | 110.6 (2) | H1FA—C1F—H1FB | 109.5 |
N2—C19—C20 | 119.0 (2) | H1FA—C1F—H1FC | 109.5 |
C20—C19—C4 | 130.2 (2) | H1FB—C1F—H1FC | 109.5 |
C19—C20—H20 | 120.4 | H1GA—C1G—H1GB | 109.5 |
C21—C20—C19 | 119.1 (3) | H1GA—C1G—H1GC | 109.5 |
C21—C20—H20 | 120.4 | H1GB—C1G—H1GC | 109.5 |
C20—C21—H21 | 119.3 | C1H—C1G—H1GA | 109.5 |
C20—C21—C22 | 121.4 (3) | C1H—C1G—H1GB | 109.5 |
C22—C21—H21 | 119.3 | C1H—C1G—H1GC | 109.5 |
C21—C22—H22 | 120.8 | C1G—C1H—H1HA | 108.6 |
C21—C22—C23 | 118.4 (2) | C1G—C1H—H1HB | 108.6 |
C23—C22—H22 | 120.8 | C1G—C1H—C1I | 114.6 (17) |
N2—C23—C22 | 119.5 (2) | H1HA—C1H—H1HB | 107.6 |
N2—C23—C24 | 110.7 (2) | C1I—C1H—H1HA | 108.6 |
C22—C23—C24 | 129.7 (2) | C1I—C1H—H1HB | 108.6 |
N3—C24—C23 | 114.4 (2) | C1H—C1I—H1IA | 109.2 |
N3—C24—C25 | 110.6 (2) | C1H—C1I—H1IB | 109.2 |
C25—C24—C23 | 134.3 (3) | H1IA—C1I—H1IB | 107.9 |
C24—C25—C26 | 105.9 (2) | C1J—C1I—C1H | 112.2 (15) |
C24—C25—C28 | 127.3 (3) | C1J—C1I—H1IA | 109.2 |
C26—C25—C28 | 126.8 (2) | C1J—C1I—H1IB | 109.2 |
C25—C26—H26 | 126.1 | C1I—C1J—H1JA | 106.4 |
C25—C26—C27 | 107.9 (2) | C1I—C1J—H1JB | 106.4 |
C27—C26—H26 | 126.1 | C1I—C1J—C1K | 123.6 (18) |
N3—C27—C26 | 109.5 (2) | H1JA—C1J—H1JB | 106.5 |
N3—C27—C35 | 124.7 (2) | C1K—C1J—H1JA | 106.4 |
C26—C27—C35 | 125.3 (2) | C1K—C1J—H1JB | 106.4 |
C29—C28—C25 | 120.9 (2) | C1J—C1K—H1KA | 110.4 |
C33—C28—C25 | 121.1 (3) | C1J—C1K—H1KB | 110.4 |
C33—C28—C29 | 118.0 (2) | C1J—C1K—C1L | 106.8 (15) |
C28—C29—H29 | 119.4 | H1KA—C1K—H1KB | 108.6 |
C30—C29—C28 | 121.3 (3) | C1L—C1K—H1KA | 110.4 |
C30—C29—H29 | 119.4 | C1L—C1K—H1KB | 110.4 |
C29—C30—H30 | 119.5 | C1K—C1L—H1LA | 109.5 |
C29—C30—C31 | 120.9 (3) | C1K—C1L—H1LB | 109.5 |
C31—C30—H30 | 119.5 | C1K—C1L—H1LC | 109.5 |
C30—C31—C34 | 120.6 (3) | H1LA—C1L—H1LB | 109.5 |
C32—C31—C30 | 117.6 (3) | H1LA—C1L—H1LC | 109.5 |
C32—C31—C34 | 121.8 (3) | H1LB—C1L—H1LC | 109.5 |
Ni—N1—C1—C2 | 161.2 (2) | C10—C5—C6—C7 | −1.9 (4) |
Ni—N1—C1—C5 | −23.5 (4) | C11—C8—C9—C10 | 178.2 (3) |
Ni—N1—C4—C3 | −166.90 (18) | C12—C3—C4—N1 | −179.7 (3) |
Ni—N1—C4—C19 | 3.1 (3) | C12—C3—C4—C19 | 13.3 (5) |
Ni—N2—C19—C4 | −6.0 (3) | C12—C13—C14—C15 | −0.1 (5) |
Ni—N2—C19—C20 | 169.9 (2) | C13—C12—C17—C16 | 3.5 (4) |
Ni—N2—C23—C22 | −170.8 (2) | C13—C14—C15—C16 | 2.4 (4) |
Ni—N2—C23—C24 | 6.5 (3) | C13—C14—C15—C18 | −177.4 (3) |
Ni—N3—C24—C23 | −7.9 (3) | C14—C15—C16—C17 | −1.7 (4) |
Ni—N3—C24—C25 | 163.61 (19) | C15—C16—C17—C12 | −1.3 (4) |
Ni—N3—C27—C26 | −156.8 (2) | C17—C12—C13—C14 | −2.8 (4) |
Ni—N3—C27—C35 | 31.3 (5) | C18—C15—C16—C17 | 178.1 (3) |
N1—Ni—N2—C19 | 6.3 (2) | C19—N2—C23—C22 | −4.1 (4) |
N1—Ni—N2—C23 | 173.5 (2) | C19—N2—C23—C24 | 173.1 (2) |
N1—C1—C2—C3 | 2.0 (3) | C19—C20—C21—C22 | −1.0 (5) |
N1—C1—C5—C6 | −48.1 (4) | C20—C21—C22—C23 | 0.2 (5) |
N1—C1—C5—C10 | 134.1 (3) | C21—C22—C23—N2 | 2.3 (4) |
N1—C4—C19—N2 | 1.7 (3) | C21—C22—C23—C24 | −174.3 (3) |
N1—C4—C19—C20 | −173.7 (3) | C22—C23—C24—N3 | 178.1 (3) |
N2—Ni—N1—C1 | −167.0 (3) | C22—C23—C24—C25 | 9.2 (5) |
N2—Ni—N1—C4 | −4.96 (19) | C23—N2—C19—C4 | −172.6 (2) |
N2—C19—C20—C21 | −0.7 (4) | C23—N2—C19—C20 | 3.3 (4) |
N2—C23—C24—N3 | 1.3 (3) | C23—C24—C25—C26 | 169.7 (3) |
N2—C23—C24—C25 | −167.6 (3) | C23—C24—C25—C28 | −11.9 (5) |
N3—Ni—N1—C1 | −177.4 (4) | C24—N3—C27—C26 | 2.5 (3) |
N3—Ni—N1—C4 | −15.3 (5) | C24—N3—C27—C35 | −169.4 (3) |
N3—Ni—N2—C19 | −176.1 (2) | C24—C25—C26—C27 | 1.1 (3) |
N3—Ni—N2—C23 | −8.8 (2) | C24—C25—C28—C29 | −55.6 (4) |
N3—C24—C25—C26 | 0.5 (3) | C24—C25—C28—C33 | 123.9 (3) |
N3—C24—C25—C28 | 178.9 (3) | C25—C26—C27—N3 | −2.2 (3) |
N3—C27—C35—C36 | −152.3 (3) | C25—C26—C27—C35 | 169.6 (3) |
N3—C27—C35—C40 | 32.6 (4) | C25—C28—C29—C30 | 178.4 (3) |
N4—Ni—N1—C1 | 1.0 (3) | C25—C28—C33—C32 | −178.8 (3) |
N4—Ni—N1—C4 | 163.01 (19) | C26—C25—C28—C29 | 122.5 (3) |
N4—Ni—N2—C19 | −85.1 (5) | C26—C25—C28—C33 | −58.0 (4) |
N4—Ni—N2—C23 | 82.1 (5) | C26—C27—C35—C36 | 37.1 (4) |
C1—N1—C4—C3 | 0.7 (3) | C26—C27—C35—C40 | −138.0 (3) |
C1—N1—C4—C19 | 170.7 (2) | C27—N3—C24—C23 | −173.4 (2) |
C1—C2—C3—C4 | −1.5 (3) | C27—N3—C24—C25 | −1.8 (3) |
C1—C2—C3—C12 | 178.7 (3) | C27—C35—C36—C37 | −176.9 (3) |
C1—C5—C6—C7 | −179.7 (3) | C27—C35—C40—C39 | 178.1 (3) |
C1—C5—C10—C9 | 179.3 (2) | C28—C25—C26—C27 | −177.3 (3) |
C2—C1—C5—C6 | 126.5 (3) | C28—C29—C30—C31 | 0.9 (4) |
C2—C1—C5—C10 | −51.2 (4) | C29—C28—C33—C32 | 0.7 (4) |
C2—C3—C4—N1 | 0.5 (3) | C29—C30—C31—C32 | −0.2 (4) |
C2—C3—C4—C19 | −166.5 (3) | C29—C30—C31—C34 | 179.5 (3) |
C2—C3—C12—C13 | 43.0 (4) | C30—C31—C32—C33 | −0.3 (5) |
C2—C3—C12—C17 | −135.9 (3) | C31—C32—C33—C28 | 0.0 (5) |
C3—C4—C19—N2 | 168.3 (3) | C33—C28—C29—C30 | −1.1 (4) |
C3—C4—C19—C20 | −7.0 (5) | C34—C31—C32—C33 | −180.0 (3) |
C3—C12—C13—C14 | 178.2 (3) | C35—C36—C37—C38 | −1.6 (5) |
C3—C12—C17—C16 | −177.5 (3) | C36—C35—C40—C39 | 2.9 (4) |
C4—N1—C1—C2 | −1.7 (3) | C36—C37—C38—C39 | 3.4 (5) |
C4—N1—C1—C5 | 173.7 (2) | C36—C37—C38—C41 | −175.8 (3) |
C4—C3—C12—C13 | −136.8 (3) | C37—C38—C39—C40 | −2.0 (5) |
C4—C3—C12—C17 | 44.3 (4) | C38—C39—C40—C35 | −1.1 (5) |
C4—C19—C20—C21 | 174.3 (3) | C40—C35—C36—C37 | −1.6 (4) |
C5—C1—C2—C3 | −173.3 (3) | C41—C38—C39—C40 | 177.1 (3) |
C5—C6—C7—C8 | 0.8 (4) | C1A—C1B—C1C—C1D | 178.1 (7) |
C6—C5—C10—C9 | 1.5 (4) | C1B—C1C—C1D—C1E | 72.3 (8) |
C6—C7—C8—C9 | 0.8 (4) | C1C—C1D—C1E—C1F | 169.8 (7) |
C6—C7—C8—C11 | −178.7 (3) | C1G—C1H—C1I—C1J | 177 (2) |
C7—C8—C9—C10 | −1.3 (4) | C1H—C1I—C1J—C1K | 130 (3) |
C8—C9—C10—C5 | 0.1 (4) | C1I—C1J—C1K—C1L | 148 (3) |
Acknowledgements
We thank Dr Muhammed Yousufuddin for the collection of data for some of the molecules presented in the manuscript.
Funding information
Funding for this research was provided by the Welch Foundation (grant No. Y-1289).
References
Abubekerov, M., Eymann, L. Y. M., Gianetti, T. L. & Arnold, J. (2016). Dalton Trans. 45, 14581–14590. Web of Science CSD CrossRef CAS PubMed Google Scholar
Adiraju, V. A. K., Jin, W., Yousufuddin, M. & Dias, H. V. R. (2020). Z. Anorg. Allg. Chem. 646, 215–219. Web of Science CSD CrossRef CAS Google Scholar
Albrecht, M. & van Koten, G. (2001). Angew. Chem. Int. Ed. 40, 3750–3781. Web of Science CrossRef CAS Google Scholar
Alig, L., Fritz, M. & Schneider, S. (2019). Chem. Rev. 119, 2681–2751. Web of Science CrossRef CAS PubMed Google Scholar
Bruker (2016). APEX2, SAINT and SADABS. Bruker AXS Inc. Madison, Wisconsin, USA. Google Scholar
Dias, H. V. R., Huai, L., Jin, W. & Bott, S. G. (1995). Inorg. Chem. 34, 1973–1974. CSD CrossRef CAS Web of Science Google Scholar
Dias, H. V. R., Jin, W., Kim, H.-J. & Lu, H.-L. (1996). Inorg. Chem. 35, 2317–2328. CSD CrossRef PubMed CAS Web of Science Google Scholar
Dias, H. V. R. & Lovely, C. J. (2008). Chem. Rev. 108, 3223–3238. Web of Science CrossRef PubMed CAS Google Scholar
Dias, H. V. R. & Lu, H.-L. (1995). Inorg. Chem. 34, 5380–5382. CSD CrossRef CAS Web of Science Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gowda, A. S., Petersen, J. L. & Milsmann, C. (2018). Inorg. Chem. 57, 1919–1934. Web of Science CSD CrossRef CAS PubMed Google Scholar
Grant, L. N., Carroll, M. E., Carroll, P. J. & Mindiola, D. J. (2016). Inorg. Chem. 55, 7997–8002. Web of Science CSD CrossRef CAS PubMed 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
Hakey, B. M., Darmon, J. M., Zhang, Y., Petersen, J. L. & Milsmann, C. (2019). Inorg. Chem. 58, 1252–1266. Web of Science CSD CrossRef CAS PubMed Google Scholar
Komine, N., Buell, R. W., Chen, C.-H., Hui, A. K., Pink, M. & Caulton, K. G. (2014). Inorg. Chem. 53, 1361–1369. Web of Science CSD CrossRef CAS PubMed Google Scholar
Moulton, C. J. & Shaw, B. L. (1976). J. Chem. Soc. Dalton Trans. pp. 1020–1024. CrossRef Web of Science Google Scholar
Peris, E. & Crabtree, R. H. (2004). Coord. Chem. Rev. 248, 2239–2246. Web of Science CrossRef CAS Google Scholar
Peris, E. & Crabtree, R. H. (2018). Chem. Soc. Rev. 47, 1959–1968. Web of Science CrossRef CAS PubMed Google Scholar
Piccirilli, L., Pinheiro, D. L. J. & Nielsen, M. (2020). Catalysts 10, 773. CrossRef Google Scholar
Pramanik, A. (2015). MS thesis, The University of Texas at Arlington, Arlington, Texas, USA. Google Scholar
Pramanik, A., Das, A., Yousufuddin, M. & Dias, H. V. R. (2014). Abstracts of Papers, 247th ACS National Meeting & Exposition, Dallas, TX, United States, March 16–20, 2014, INOR-266. Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sorsche, D., Miehlich, M., Searles, K., Gouget, G., Zolnhofer, E. M., Fortier, S., Chen, C.-H., Gau, M. R., Carroll, P. J., Murray, C. B., Caulton, K. G., Khusniyarov, M. M., Meyer, K. & Mindiola, D. J. (2020). J. Am. Chem. Soc. 142, 8147–8159. Web of Science CSD CrossRef PubMed Google Scholar
Tapper, A. E., Billo, E. J. & Golen, J. A. (1993). Inorg. Chim. Acta, 210, 71–75. CAS Google Scholar
Yadav, S., Singh, A., Rashid, N., Ghotia, M., Roy, T. K., Ingole, P. P., Ray, S., Mobin, S. M. & Dash, C. (2018). ChemistrySelect 3, 9469–9475. Web of Science CSD CrossRef CAS Google Scholar
Yang, J.-X., Tao, X.-T., Yuan, C. X., Yan, Y. X., Wang, L., Liu, Z., Ren, Y. & Jiang, M. H. (2005). J. Am. Chem. Soc. 127, 3278–3279. Web of Science CrossRef PubMed CAS Google Scholar
Zhang, Y., Lee, T. S., Favale, J. M., Leary, D. C., Petersen, J. L., Scholes, G. D., Castellano, F. N. & Milsmann, C. (2020). Nat. Chem. 12, 345–352. Web of Science CSD CrossRef CAS PubMed Google Scholar
Zhang, Y., Petersen, J. L. & Milsmann, C. (2016). J. Am. Chem. Soc. 138, 13115–13118. Web of Science CSD CrossRef CAS PubMed Google Scholar
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