research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

Synthesis and crystal structure of a disubstituted nickel(II) bis­­[(di­methyl­amino­phenyl­imino)­eth­yl]pyridine chloride complex

aDepartment of Chemistry and Physics, Saint Mary's College, Notre Dame, IN 46556, USA, and bDepartment of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556-5670, USA
*Correspondence e-mail: dbabbini@saintmarys.edu

Edited by M. Weil, Vienna University of Technology, Austria (Received 30 June 2017; accepted 6 July 2017; online 13 July 2017)

The solvated title compound, bis­[2,6-bis­(1-{[4-(di­methyl­amino)­phen­yl]imino-κN}eth­yl)pyridine-κN]nickel(II) dichloride–di­chloro­methane–water (1/2/2), [Ni(C25H29N5)2]Cl2·2CH2Cl2·2H2O, represents a nickel(II) bis­(pyridine di­imine) complex with electron-donating di­methyl­amino­phenyl substituents. The complex crystallizes as a water/di­chloro­methane solvate with Z′ = 2, thus the asymmetric unit consists of two NiII complex cations, four chloride anions, four adventitious water and four di­chloro­methane solvent mol­ecules. Around each octa­hedrally coordinated NiII cation, one pendant phenyl group on each of the two ligands has an intra­molecular ππ inter­action with the pyridine ring of the other chelating ligand. In the crystal, pairs of water mol­ecules are hydrogen bonded to pairs of chlorine atoms. The di­chloro­methane solvent mol­ecules are likewise hydrogen bonded to the chloride anions.

1. Chemical context

Non-innocent ligand systems in organometallics can produce secondary reactivity and allow for unique mechanistic and redox properties (Babbini & Iluc, 2015[Babbini, D. C. & Iluc, V. M. (2015). Organometallics, 34, 3141-3151.]; Praneeth et al., 2012[Praneeth, V. K., Ringenberg, M. R. & Ward, T. R. (2012). Angew. Chem. Int. Ed. 51, 10228-10234.]). Redox non-innocence is usually observed with chelate ligands which possess low-lying π-systems that can allow for electron transfer (Lyaskovskyy & de Bruin, 2012[Lyaskovskyy, V. & de Bruin, B. (2012). ACS Catal. 2, 270-279.]). These ligand systems can also allow for multiple-electron redox events to take place on metal cations which are usually relegated to single-electron events (Haneline & Heyduk, 2006[Haneline, M. R. & Heyduk, A. F. (2006). J. Am. Chem. Soc. 128, 8410-8411.]). This can allow for the utilization of benign and economically viable base metal catalysts in lieu of traditional noble-metal catalysts (Chirik & Wieghardt, 2010[Chirik, P. J. & Wieghardt, K. (2010). Science, 327, 794-795.]). The development of new and varied organometallic complexes is essential for understanding the structure–property relationships, which give rise to redox non-innocence properties. With expanding inter­est in redox-active organometallic systems, we report here the synthesis and structural determination of a potentially redox-active nickel(II) complex possessing two pyridine di­imine ligands containing electron-donating substituents.

2. Structural commentary

The title compounds crystallizes with two complex NiII cations, associated chloride anions, adventitious water and di­chloro­methane mol­ecules of solvation in the asymmetric unit (Fig. 1[link]). Although the two cations are crystallographically independent they are chemically identical and the general discussion for one, holds for the second mol­ecule. We inspected the structure for higher and missed symmetry (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]), but there is none.

[Scheme 1]
[Figure 1]
Figure 1
Selective labelling scheme for [Ni(C25H29N5)2]Cl2·2CH2Cl2·2H2O. Atomic displacement ellipsoids are depicted at the 50% probability level and H atoms shown as spheres of arbitrary radius. Hydrogen-bonding inter­actions are denoted as blue, dashed lines.

Each nickel(II) cation is coordinated in a distorted octa­hedral geometry by the imine and pyridine nitro­gen atoms of the two tridentate 2,6-bis­[1-(4-di­methyl­amino­phenyl­imino)­eth­yl]pyridine (PDI-DMA) ligands (Fig. 1[link], Table 1[link] for numerical details). The derived metrics for the mol­ecules are as expected. It should be noted that the Ni—Npy bond lengths are all considerably shorter than the Ni—Nimine bond lengths. However, both inter­actions are typical for these types of bonds/moieties.

Table 1
Selected geometric parameters (Å, °)

Ni1—N2 1.9694 (18) Ni2—N12 1.9658 (18)
Ni1—N5 1.9725 (18) Ni2—N15 1.9711 (18)
Ni1—N3 2.0844 (18) Ni2—N14 2.0909 (19)
Ni1—N4 2.0948 (19) Ni2—N11 2.0977 (19)
Ni1—N1 2.1243 (19) Ni2—N13 2.1188 (19)
Ni1—N6 2.1354 (19) Ni2—N16 2.141 (2)
       
N2—Ni1—N5 167.57 (8) N12—Ni2—N15 167.94 (8)
N2—Ni1—N3 77.92 (7) N12—Ni2—N14 110.67 (7)
N5—Ni1—N3 111.32 (7) N15—Ni2—N14 78.01 (7)
N2—Ni1—N4 110.91 (7) N12—Ni2—N11 77.79 (7)
N5—Ni1—N4 77.83 (8) N15—Ni2—N11 111.03 (7)
N3—Ni1—N4 92.14 (7) N14—Ni2—N11 91.70 (7)
N2—Ni1—N1 76.66 (7) N12—Ni2—N13 76.89 (7)
N5—Ni1—N1 94.65 (7) N15—Ni2—N13 94.86 (7)
N3—Ni1—N1 153.98 (7) N14—Ni2—N13 91.88 (7)
N4—Ni1—N1 91.75 (7) N11—Ni2—N13 154.04 (7)
N2—Ni1—N6 94.89 (7) N12—Ni2—N16 94.74 (7)
N5—Ni1—N6 76.68 (8) N15—Ni2—N16 76.75 (8)
N3—Ni1—N6 93.36 (7) N14—Ni2—N16 154.58 (7)
N4—Ni1—N6 154.19 (7) N11—Ni2—N16 94.50 (7)
N1—Ni1—N6 94.25 (7) N13—Ni2—N16 93.21 (7)

An inter­esting feature of the cations is the orientation of the pendant di­methyl­amino­phenyl rings with respect to the pyridine ring of each ligand. In all cases, one pendant phenyl group is oriented close to perpendicular to the plane of the parent pyridine ring while the other is canted at an angle of around 60° (Fig. 2[link]); numerical details of these features are collated in Table 2[link]. Inspection of the mol­ecules shows that a combination of steric and ππ stacking inter­actions are the cause of these orientations. The phenyl rings that are close to perpendicular to the parent pyridine are sterically constrained by the pyridine rings of the second ligand and include weak intra­molecular ππ inter­actions (Table 2[link]). The second di­methyl­amino­phenyl group is less hindered and adopts a typical tilted orientation.

Table 2
Inter­planar angles and close ππ inter­actions (Å, °)

Phenyl ring Pyridine ring Angle
C19–C24 N2–C7 87.58 (6)
C27–C28 N2–C7 64.85 (7)
C35–C40 N5–C16 54.42 (8)
C43–C48 N5–C16 83.76 (6)
C69–C74 N12–C57 63.47 (7)
C77–C82 N12–C57 87.83 (6)
C85–C90 N15–C66 53.63 (8)
C93–C98 N15–C66 81.53 (7)
     
Phenyl ring Pyridine ring Cg1⋯Cg2
C43–C48 N2–C7 3.487 (1)
C19–C24 N5–C46 3.675 (1)
C93–C98 N12–C57 3.520 (1)
C85–C90 N15–C66 3.696 (1)
Cg1 and Cg2 are the centroids for the named phenyl and pyridine rings.
[Figure 2]
Figure 2
A single cationic unit (Ni1) displaying intra­molecular ππ inter­actions between phenyl and pyridyl rings.

3. Supra­molecular features

Within the inter­molecular packing of the cationic mol­ecules pairs of solvent water mol­ecules form a hydrogen-bonded dimer with pairs of chloride anions (Fig. 1[link], Table 3[link]). Each di­chloro­methane solvent mol­ecule also forms a weak, but directional, hydrogen bond with a chloride anion (Table 3[link]). Surprisingly, the cation does not have any particular directional inter­actions with other species in the structure, aside from a weak C—H⋯N inter­action with one of the di­chloro­methane solvents (Table 3[link]) and typical van der Waals contacts (Fig. 3[link]).

Table 3
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1OA⋯Cl1 0.91 2.33 3.2381 (19) 177
O1—H1OB⋯Cl2 0.88 2.31 3.188 (2) 177
O2—H2OA⋯Cl1 1.01 2.18 3.192 (2) 175
O2—H2OB⋯Cl2 0.95 2.32 3.2691 (19) 177
O3—H3OA⋯Cl4 0.90 2.30 3.198 (2) 178
O3—H3OB⋯Cl3 0.87 2.34 3.201 (2) 174
O4—H4OB⋯Cl3 1.08 2.12 3.180 (2) 168
O4—H4OA⋯Cl4 0.94 2.25 3.192 (2) 177
C1S—H1SB⋯Cl3 0.99 2.47 3.422 (3) 162
C2S—H2SA⋯Cl4 0.99 2.81 3.743 (4) 158
C2S—H2SB⋯Cl1i 0.99 2.66 3.642 (3) 169
C3S—H3SA⋯N17ii 0.99 2.42 3.403 (4) 173
C3S—H3SB⋯Cl2 0.99 2.49 3.447 (3) 163
C4S—H4SA⋯Cl4 0.99 2.54 3.527 (3) 176
Symmetry codes: (i) x, y+1, z; (ii) x-1, y, z.
[Figure 3]
Figure 3
Packing diagram of [Ni(C25H29N5)2]Cl2·2CH2Cl2·2H2O, viewed along the a axis.

4. Database survey

A search of the Cambridge Structure Database (Version 5.38 + three updates; Groom et al., 2016[Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171-179.]) reveals 13 structures that incorporate NiII coordinated by two bis-imino­aryl­pyridyl ligands. Of these, there are only three related structures with the imine carbon atoms methyl­ated (FADFUN, Patel et al., 2010[Patel, R. N., Shukla, K. K., Singh, A., Choudhary, M., Patel, D. K., Niclós-Gutiérrez, J. & Choquesillo-Lazarte, D. (2010). J. Coord. Chem. 63, 3648-3661.]; MEGDUX, de Bruin et al., 2000[Bruin, B. de, Bill, E., Bothe, E., Weyhermüller, T. & Wieghardt, K. (2000). Inorg. Chem. 39, 2936-2947.]; QEZJOV, Trivedi et al., 2007[Trivedi, M., Pandey, D. S. & Xu, Q. (2007). Inorg. Chim. Acta, 360, 2492-2498.]).

5. Synthesis and crystallization

The reagent 2,6-di­acetyl­pyridine was synthesized according to a previously reported method (Su & Feng, 2010[Su, B. & Feng, G. (2010). Polym. Int. 59, 1058-1063.]). The ligand was prepared by a modification of previously reported Schiff-base condensation methods (Small & Brookhart, 1999[Small, B. L. & Brookhart, M. (1999). Macromolecules, 32, 2120-2130.]; Chen et al., 2003[Chen, Y., Chen, R., Qian, C., Dong, X. & Sun, J. (2003). Organometallics, 22, 4312-4321.]). All other reagents and solvents were purchased commercially and used without further purification. 1H NMR data were collected on a Varian 60 MHz NMR. Mass spectra were collected using direct injection on a ThermoScientific TSQ–ESI Mass spectrometer.

Synthesis of 2,6-bis­(1-(4-di­methyl­amino­phenyl­imino)­eth­yl)pyridine (PDI-DMA). A solution of 2,6-di­acetyl­pyridine (1.0 g, 6.10 mmol), 4-(di­methyl­amino)­aniline (1.7 g, 12.5 mmol) and formic acid (1 ml) was prepared in toluene (100 ml) under nitro­gen atmosphere and then stirred for 12 h on mol­ecular sieves. The reaction mixture was filtered and extracted with excess di­chloro­methane, then the amount of solvent was reduced in vacuo. The crude yellow product was then washed with cold methanol, followed by diethyl ether and filtered producing a pure bright-yellow solid (yield 1.8 g, 72.7% yield). 1H NMR (60 MHz, CDCl3, 293 K): δ 8.4–8.2 (m, 2H, Py-H), 7.9–7.8 (m, 1H, Py-H), 6.8 (m, 8H, Ar-H) 3.0 (s, 12H, N-CH3), 2.5 (s, 6H, CH3). MS (ESI): 400.4 m/z [C25H29N5]H+.

Synthesis of [bis-(2,6-bis-(1-(4-di­methyl­amino­phenyl­imino)­eth­yl)pyridine)­nickel(II)] chloride. A solution of the PDI-DMA ligand (300 mg, 0.75 mmol) and nickel(II) chloride (48.7 mg, 0.38 mmol) was prepared in THF (15 ml) under nitro­gen atmosphere, then stirred for 12 h. The solution was filtered and extracted with di­chloro­methane. The solvent was removed in vacuo yielding a dark reddish-brown solid (yield 220 mg, 67.5% yield). X-ray diffraction quality crystals were isolated as red–brown blocks by vapor diffusion of hexa­nes into a saturated solution of the product and di­chloro­methane. The complex was NMR silent (paramagnetic). MS (ESI): m/z 855.5 [C50H57N10Ni]+.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 4[link]. H atoms bonded to carbon were placed in geometric positions with C—H = 0.95, 0.99 and 0.98 Å and Uiso(H) = 1.2 ×, 1.2 × or 1.5 × Ueq(C) for aromatic, methyl­ene and methyl H atoms, successively. Water H atoms were initially located from a difference Fourier map and included in their initially observed positions and allowed to ride with the position of the parent oxygen atom. Displacement parameters of the hydrogen atom were freely refined. Two reflections ([\overline{3}]41 and 0,10,2) were omitted from the refinement for poorly agreeing statistics. It is not clear from the diffraction data why these two reflections agree poorly.

Table 4
Experimental details

Crystal data
Chemical formula [Ni(C25H29N5)2]Cl2·2CH2Cl2·2H2O
Mr 1134.55
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 120
a, b, c (Å) 13.2227 (5), 17.7311 (6), 24.0242 (9)
α, β, γ (°) 79.6276 (12), 81.2551 (12), 89.3481 (12)
V3) 5475.4 (3)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.70
Crystal size (mm) 0.30 × 0.22 × 0.15
 
Data collection
Diffractometer Bruker Kappa X8 APEXII
Absorption correction Numerical (SADABS; Krause et al., 2015[Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3-10.])
Tmin, Tmax 0.823, 0.917
No. of measured, independent and observed [I > 2σ(I)] reflections 69305, 24260, 17532
Rint 0.034
(sin θ/λ)max−1) 0.643
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.115, 1.04
No. of reflections 24260
No. of parameters 1315
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 1.19, −1.00
Computer programs: APEX3 and SAINT (Bruker, 2016[Bruker. (2016). APEX3 and SAINT. Bruker AXS Inc. Madison, Wisconsin, USA.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2014 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]), POV-RAY (Cason, 2003[Cason, C. J. (2003). POV-RAY. Persistence of Vision Raytracer Pty. Ltd, Victoria, Australia.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2006) and POV-RAY (Cason, 2003); software used to prepare material for publication: publCIF (Westrip, 2010).

Bis[2,6-bis(1-{[4-(dimethylamino)phenyl]imino-κN}ethyl)pyridine-κN]nickel dichloride–dichloromethane–water (1/2/2) top
Crystal data top
[Ni(C25H29N5)2]Cl2·2CH2Cl2·2H2OZ = 4
Mr = 1134.55F(000) = 2376
Triclinic, P1Dx = 1.376 Mg m3
a = 13.2227 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 17.7311 (6) ÅCell parameters from 9951 reflections
c = 24.0242 (9) Åθ = 2.3–27.1°
α = 79.6276 (12)°µ = 0.70 mm1
β = 81.2551 (12)°T = 120 K
γ = 89.3481 (12)°Block, red-brown
V = 5475.4 (3) Å30.30 × 0.22 × 0.15 mm
Data collection top
Bruker Kappa X8 APEXII
diffractometer
24260 independent reflections
Radiation source: fine-focus sealed tube17532 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
Detector resolution: 8.33 pixels mm-1θmax = 27.2°, θmin = 0.9°
combination of ω and φ–scansh = 1617
Absorption correction: numerical
(SADABS; Krause et al., 2015)
k = 2217
Tmin = 0.823, Tmax = 0.917l = 3030
69305 measured reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: mixed
wR(F2) = 0.115H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0506P)2 + 2.6902P]
where P = (Fo2 + 2Fc2)/3
24260 reflections(Δ/σ)max = 0.001
1315 parametersΔρmax = 1.19 e Å3
0 restraintsΔρmin = 1.00 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.94318 (2)0.75736 (2)0.49692 (2)0.01340 (7)
N11.05673 (14)0.67220 (11)0.49125 (8)0.0166 (4)
N20.95646 (14)0.71811 (10)0.57750 (8)0.0144 (4)
N30.82707 (14)0.81477 (10)0.54041 (8)0.0144 (4)
N40.83769 (14)0.69100 (11)0.46895 (8)0.0159 (4)
N50.96256 (14)0.79725 (11)0.41383 (8)0.0160 (4)
N61.05128 (14)0.84927 (11)0.48658 (8)0.0175 (4)
N71.1429 (2)0.59662 (16)0.27296 (10)0.0457 (7)
N80.52711 (16)0.97392 (12)0.42701 (9)0.0280 (5)
N90.55000 (15)0.49107 (12)0.61881 (8)0.0227 (5)
N101.15686 (17)0.90581 (13)0.69285 (9)0.0296 (5)
C11.16227 (19)0.57935 (14)0.54579 (11)0.0233 (5)
H1A1.1363170.5394450.5785380.035*
H1B1.2259160.6014820.5525290.035*
H1C1.1755570.5568350.5110470.035*
C21.08458 (17)0.64073 (13)0.53853 (10)0.0168 (5)
C31.03387 (17)0.67150 (13)0.58929 (10)0.0167 (5)
C41.06214 (18)0.65800 (13)0.64315 (10)0.0194 (5)
H41.1160340.6240520.6516820.023*
C51.00967 (19)0.69538 (14)0.68448 (10)0.0228 (5)
H51.0285000.6876380.7216840.027*
C60.93018 (18)0.74383 (13)0.67207 (9)0.0194 (5)
H60.8939020.7694710.7002570.023*
C70.90505 (17)0.75385 (13)0.61731 (9)0.0161 (5)
C80.82490 (17)0.80492 (13)0.59496 (9)0.0173 (5)
C90.7536 (2)0.84156 (15)0.63575 (10)0.0260 (6)
H9A0.7212650.8853800.6146040.039*
H9B0.7916100.8592290.6630710.039*
H9C0.7007070.8042270.6564810.039*
C100.7904 (2)0.65176 (15)0.38197 (10)0.0257 (6)
H10A0.8412030.6326360.3538840.039*
H10B0.7404560.6828010.3621000.039*
H10C0.7552110.6083110.4086340.039*
C110.84277 (17)0.69971 (13)0.41435 (9)0.0168 (5)
C120.91471 (18)0.76121 (13)0.38117 (9)0.0186 (5)
C130.9351 (2)0.78081 (15)0.32215 (10)0.0248 (6)
H130.9001430.7556880.2987390.030*
C141.0075 (2)0.83771 (15)0.29787 (10)0.0289 (6)
H141.0213110.8529800.2574420.035*
C151.05953 (19)0.87230 (14)0.33243 (10)0.0238 (5)
H151.1109140.9102940.3162290.029*
C161.03522 (18)0.85042 (13)0.39117 (10)0.0185 (5)
C171.08515 (17)0.87935 (13)0.43460 (10)0.0184 (5)
C181.17011 (19)0.93686 (15)0.41517 (11)0.0261 (6)
H18A1.2281200.9138480.3940990.039*
H18B1.1914500.9532660.4485130.039*
H18C1.1466900.9813320.3901080.039*
C191.08983 (17)0.64669 (13)0.43826 (10)0.0178 (5)
C201.16176 (18)0.68909 (14)0.39652 (10)0.0230 (5)
H201.1980770.7300990.4055270.028*
C211.18083 (19)0.67215 (15)0.34221 (11)0.0251 (6)
H211.2307420.7013070.3142210.030*
C221.1274 (2)0.61228 (15)0.32767 (10)0.0271 (6)
C231.05641 (19)0.56951 (14)0.37042 (10)0.0225 (5)
H231.0205200.5278330.3620440.027*
C241.03783 (18)0.58720 (13)0.42482 (10)0.0193 (5)
H240.9886370.5579660.4532140.023*
C251.0827 (3)0.53817 (19)0.25846 (13)0.0521 (9)
H25A1.0948870.5405490.2169090.078*
H25B1.0099990.5463800.2709930.078*
H25C1.1020910.4876980.2775960.078*
C261.2234 (3)0.6350 (2)0.23073 (12)0.0498 (9)
H26A1.2207980.6190960.1939610.075*
H26B1.2897510.6215670.2429020.075*
H26C1.2145230.6906100.2265080.075*
C270.74965 (17)0.85605 (13)0.51336 (9)0.0157 (5)
C280.64669 (18)0.83715 (13)0.53030 (10)0.0187 (5)
H280.6267680.7972870.5621450.022*
C290.57299 (18)0.87494 (14)0.50192 (10)0.0203 (5)
H290.5030670.8604250.5140360.024*
C300.59985 (18)0.93470 (13)0.45527 (10)0.0196 (5)
C310.70425 (18)0.95273 (14)0.43811 (10)0.0208 (5)
H310.7248530.9927560.4064810.025*
C320.77730 (18)0.91340 (13)0.46633 (10)0.0189 (5)
H320.8476510.9257890.4533460.023*
C330.42161 (19)0.94824 (15)0.43961 (12)0.0300 (6)
H33A0.3810300.9821070.4149580.045*
H33B0.3952520.9494510.4798270.045*
H33C0.4168740.8957240.4325980.045*
C340.5576 (2)1.03030 (16)0.37651 (12)0.0341 (7)
H34A0.6017311.0066180.3480580.051*
H34B0.5952341.0721500.3863260.051*
H34C0.4967551.0506680.3606550.051*
C350.76478 (17)0.63922 (13)0.50586 (9)0.0166 (5)
C360.79552 (18)0.58544 (13)0.54891 (10)0.0190 (5)
H360.8655800.5832620.5536550.023*
C370.72591 (18)0.53484 (14)0.58508 (10)0.0204 (5)
H370.7492180.4971770.6135130.024*
C380.62107 (18)0.53799 (14)0.58066 (10)0.0195 (5)
C390.59132 (18)0.59409 (14)0.53729 (10)0.0217 (5)
H390.5210860.5979140.5330230.026*
C400.66142 (18)0.64363 (14)0.50083 (10)0.0207 (5)
H400.6390190.6811470.4719840.025*
C410.5864 (2)0.42651 (15)0.65642 (11)0.0318 (6)
H41A0.6213220.3907740.6334830.048*
H41B0.5281450.4001960.6825710.048*
H41C0.6341610.4449380.6786090.048*
C420.4508 (2)0.47877 (16)0.60241 (11)0.0310 (6)
H42A0.4606000.4592910.5663170.047*
H42B0.4143370.5273780.5974680.047*
H42C0.4106400.4413540.6323860.047*
C431.08716 (17)0.87102 (13)0.53470 (10)0.0176 (5)
C441.16933 (18)0.83543 (14)0.55673 (11)0.0223 (5)
H441.2105600.8026410.5358130.027*
C451.19257 (18)0.84671 (14)0.60863 (11)0.0228 (5)
H451.2494120.8212340.6229690.027*
C461.13421 (19)0.89493 (14)0.64076 (10)0.0213 (5)
C471.05252 (19)0.93204 (14)0.61710 (10)0.0221 (5)
H471.0123410.9663450.6370600.026*
C481.02924 (18)0.91978 (13)0.56543 (10)0.0207 (5)
H480.9726960.9451090.5506480.025*
C491.2292 (2)0.85579 (16)0.72049 (11)0.0301 (6)
H49A1.2971610.8636520.6972960.045*
H49B1.2072230.8022560.7243230.045*
H49C1.2320310.8676630.7585180.045*
C501.0876 (3)0.94759 (19)0.72748 (12)0.0452 (8)
H50A1.0840521.0006440.7075310.068*
H50B1.1119210.9471650.7640810.068*
H50C1.0193730.9235090.7345190.068*
Ni20.56947 (2)0.24363 (2)0.00835 (2)0.01385 (7)
N110.68705 (14)0.18659 (10)0.03550 (8)0.0155 (4)
N120.55080 (14)0.27763 (10)0.07190 (8)0.0151 (4)
N130.45280 (14)0.32605 (11)0.01389 (8)0.0171 (4)
N140.67462 (14)0.31505 (11)0.03144 (8)0.0161 (4)
N150.55654 (14)0.20771 (11)0.09172 (8)0.0150 (4)
N160.46245 (14)0.14972 (11)0.02362 (8)0.0182 (4)
N170.99169 (15)0.04118 (12)0.08291 (9)0.0242 (5)
N180.37685 (19)0.41271 (14)0.22925 (9)0.0357 (6)
N190.94578 (16)0.51957 (12)0.12614 (8)0.0237 (5)
N200.31106 (17)0.09062 (12)0.17089 (9)0.0262 (5)
C510.7577 (2)0.15726 (15)0.13050 (10)0.0269 (6)
H51A0.7188180.1370600.1563530.040*
H51B0.7929330.1151880.1092640.040*
H51C0.8082920.1952710.1528670.040*
C520.68663 (17)0.19410 (13)0.08951 (10)0.0171 (5)
C530.60277 (17)0.24198 (13)0.11123 (9)0.0166 (5)
C540.57646 (19)0.24980 (14)0.16545 (10)0.0213 (5)
H540.6135530.2241990.1934120.026*
C550.49485 (19)0.29578 (15)0.17801 (10)0.0238 (5)
H550.4754710.3021400.2150400.029*
C560.44113 (18)0.33270 (14)0.13672 (10)0.0206 (5)
H560.3853700.3648350.1450400.025*
C570.47085 (17)0.32147 (13)0.08330 (10)0.0167 (5)
C580.41979 (17)0.35308 (13)0.03301 (10)0.0166 (5)
C590.33651 (19)0.40976 (14)0.03978 (11)0.0241 (6)
H59A0.3582570.4500450.0730320.036*
H59B0.3216690.4326840.0052890.036*
H59C0.2748250.3838350.0454750.036*
C600.72346 (19)0.36265 (15)0.11472 (10)0.0250 (6)
H60A0.7790310.3360040.1324910.037*
H60B0.6734510.3796280.1442310.037*
H60C0.7514600.4072720.0864720.037*
C610.67234 (17)0.30942 (13)0.08571 (9)0.0172 (5)
C620.60561 (18)0.24702 (13)0.12198 (10)0.0185 (5)
C630.59120 (19)0.22916 (15)0.18118 (10)0.0236 (5)
H630.6264340.2569670.2028460.028*
C640.5243 (2)0.16992 (15)0.20789 (10)0.0275 (6)
H640.5149480.1554670.2483990.033*
C650.47086 (19)0.13146 (15)0.17613 (10)0.0242 (6)
H650.4233950.0914850.1943320.029*
C660.48824 (17)0.15267 (13)0.11720 (10)0.0179 (5)
C670.43353 (17)0.12126 (13)0.07645 (10)0.0176 (5)
C680.34921 (18)0.06396 (14)0.09959 (10)0.0237 (5)
H68A0.2921970.0882990.1204060.036*
H68B0.3741530.0212700.1256540.036*
H68C0.3257860.0446060.0679200.036*
C690.76642 (17)0.14784 (13)0.00836 (9)0.0157 (5)
C700.86890 (18)0.16776 (14)0.02611 (10)0.0197 (5)
H700.8880060.2062120.0590090.024*
C710.94330 (18)0.13256 (14)0.00329 (10)0.0198 (5)
H711.0130150.1471650.0096120.024*
C720.91799 (18)0.07570 (13)0.05183 (10)0.0187 (5)
C730.81430 (17)0.05617 (13)0.06959 (10)0.0186 (5)
H730.7946960.0174900.1022800.022*
C740.74035 (18)0.09244 (13)0.04017 (9)0.0181 (5)
H740.6703210.0791780.0534330.022*
C751.09837 (18)0.04733 (15)0.05675 (12)0.0283 (6)
H75A1.1076470.0222140.0232120.042*
H75B1.1410150.0223760.0844910.042*
H75C1.1184760.1015500.0448750.042*
C760.9646 (2)0.02654 (15)0.12591 (11)0.0296 (6)
H76A0.9048290.0160170.1527820.044*
H76B1.0222310.0406810.1467070.044*
H76C0.9482180.0688580.1074010.044*
C770.42147 (17)0.35379 (13)0.06615 (9)0.0173 (5)
C780.47223 (18)0.41554 (14)0.07687 (10)0.0197 (5)
H780.5184290.4450660.0469390.024*
C790.45709 (19)0.43536 (14)0.13060 (10)0.0228 (5)
H790.4928650.4783650.1370580.027*
C800.3896 (2)0.39279 (15)0.17561 (10)0.0239 (5)
C810.33736 (19)0.33057 (15)0.16367 (11)0.0251 (6)
H810.2901040.3011860.1931120.030*
C820.35333 (18)0.31143 (14)0.11014 (10)0.0213 (5)
H820.3174700.2688290.1031090.026*
C830.4592 (3)0.4527 (2)0.24455 (13)0.0533 (9)
H83A0.5234000.4260660.2358600.080*
H83B0.4457620.4542450.2855870.080*
H83C0.4646360.5051610.2226710.080*
C840.3087 (3)0.3664 (2)0.27473 (12)0.0478 (8)
H84A0.2413380.3631360.2629390.072*
H84B0.3019690.3896750.3091040.072*
H84C0.3364030.3147610.2830870.072*
C850.74349 (17)0.36746 (13)0.00769 (10)0.0172 (5)
C860.84744 (18)0.36710 (14)0.00498 (10)0.0214 (5)
H860.8733010.3314110.0237200.026*
C870.91370 (19)0.41760 (14)0.04322 (10)0.0225 (5)
H870.9845520.4165250.0402520.027*
C880.87861 (18)0.47075 (14)0.08657 (10)0.0196 (5)
C890.77311 (18)0.47017 (14)0.08890 (10)0.0203 (5)
H890.7464540.5060140.1171970.024*
C900.70755 (18)0.41854 (14)0.05086 (10)0.0191 (5)
H900.6369260.4179420.0542580.023*
C911.04661 (19)0.53340 (16)0.11291 (11)0.0295 (6)
H91A1.0857770.5680070.1452050.044*
H91B1.0823410.4846640.1059750.044*
H91C1.0398460.5568600.0786080.044*
C920.9038 (2)0.58500 (16)0.16033 (11)0.0312 (6)
H92A0.9588740.6125160.1883090.047*
H92B0.8721680.6194540.1352920.047*
H92C0.8522040.5671990.1804710.047*
C930.41735 (17)0.12778 (13)0.02151 (9)0.0175 (5)
C940.32708 (18)0.15923 (14)0.03611 (11)0.0237 (5)
H940.2884810.1898380.0121750.028*
C950.29206 (19)0.14689 (14)0.08494 (11)0.0257 (6)
H950.2293220.1689000.0938190.031*
C960.34662 (19)0.10272 (13)0.12180 (10)0.0208 (5)
C970.43628 (19)0.06970 (14)0.10535 (11)0.0236 (5)
H970.4741480.0375870.1283400.028*
C980.47125 (18)0.08247 (13)0.05667 (10)0.0207 (5)
H980.5332450.0598570.0470810.025*
C990.2497 (2)0.15044 (16)0.19891 (11)0.0339 (7)
H99A0.2287280.1345160.2325160.051*
H99B0.2903110.1980640.2109360.051*
H99C0.1887930.1589340.1720990.051*
C1000.3762 (2)0.05017 (18)0.20938 (12)0.0392 (7)
H10D0.3415240.0448900.2417660.059*
H10E0.3907240.0008100.1889090.059*
H10F0.4405480.0790420.2235310.059*
Cl10.32592 (6)0.13439 (4)0.27016 (3)0.03678 (17)
Cl20.20244 (5)0.14063 (4)0.22310 (3)0.02772 (14)
Cl30.78142 (5)0.36539 (4)0.24816 (3)0.02773 (15)
Cl40.68265 (5)0.64160 (4)0.26307 (3)0.02594 (14)
C1S0.5820 (2)0.32718 (17)0.35855 (12)0.0371 (7)
H1SA0.5313640.3682010.3623270.045*
H1SB0.6411930.3489950.3300200.045*
Cl50.52651 (6)0.25141 (5)0.33470 (4)0.0515 (2)
Cl60.62287 (6)0.29465 (5)0.42512 (3)0.04281 (19)
C2S0.5202 (3)0.76821 (19)0.34787 (13)0.0475 (9)
H2SA0.5459270.7248860.3291450.057*
H2SB0.4752150.7991670.3235300.057*
Cl70.44865 (7)0.73200 (5)0.41754 (4)0.0514 (2)
Cl80.62339 (7)0.82496 (5)0.35527 (3)0.0502 (2)
C3S0.0469 (2)0.20879 (16)0.12292 (12)0.0352 (7)
H3SA0.0255190.1595760.1139330.042*
H3SB0.1017000.1979480.1469710.042*
Cl90.09611 (6)0.27075 (4)0.05845 (3)0.04107 (18)
Cl100.05734 (6)0.24757 (5)0.16151 (4)0.0514 (2)
C4S0.9087 (2)0.65869 (17)0.16231 (12)0.0381 (7)
H4SA0.8447610.6515710.1902300.046*
H4SB0.9414600.6081520.1627160.046*
Cl110.87950 (6)0.69424 (4)0.09336 (3)0.04264 (19)
Cl120.99139 (6)0.72231 (5)0.18242 (4)0.0502 (2)
O10.15979 (14)0.03002 (11)0.20668 (7)0.0298 (4)
H1OA0.2084210.0579220.2234740.049 (10)*
H1OB0.1733210.0163780.2119740.061 (11)*
O20.35472 (14)0.03293 (11)0.29766 (7)0.0331 (4)
H2OA0.3495780.0195090.2871100.074 (12)*
H2OB0.3101780.0653910.2771100.082 (13)*
O30.70769 (17)0.52151 (11)0.17747 (8)0.0409 (5)
H3OA0.7021360.5553090.2014150.068 (12)*
H3OB0.7321360.4796890.1948950.087 (14)*
O40.8157 (2)0.50164 (12)0.31347 (10)0.0597 (7)
H4OA0.7747720.5415060.2983670.067 (11)*
H4OB0.7993920.4611760.2874970.16 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.01361 (15)0.01447 (15)0.01276 (14)0.00145 (12)0.00309 (11)0.00332 (11)
N10.0149 (10)0.0183 (10)0.0183 (10)0.0020 (8)0.0039 (8)0.0069 (8)
N20.0146 (10)0.0134 (10)0.0162 (9)0.0004 (8)0.0040 (7)0.0042 (8)
N30.0144 (10)0.0126 (10)0.0163 (10)0.0001 (8)0.0020 (7)0.0027 (8)
N40.0154 (10)0.0153 (10)0.0189 (10)0.0027 (8)0.0056 (8)0.0061 (8)
N50.0150 (10)0.0156 (10)0.0171 (10)0.0045 (8)0.0023 (8)0.0027 (8)
N60.0136 (10)0.0166 (10)0.0228 (10)0.0009 (8)0.0020 (8)0.0053 (8)
N70.0616 (18)0.0553 (18)0.0196 (12)0.0070 (14)0.0054 (11)0.0146 (12)
N80.0188 (11)0.0269 (12)0.0361 (13)0.0039 (9)0.0085 (9)0.0036 (10)
N90.0185 (11)0.0253 (12)0.0244 (11)0.0042 (9)0.0017 (8)0.0054 (9)
N100.0341 (13)0.0290 (13)0.0323 (12)0.0119 (10)0.0155 (10)0.0152 (10)
C10.0219 (13)0.0217 (13)0.0276 (13)0.0070 (11)0.0080 (10)0.0044 (11)
C20.0134 (11)0.0156 (12)0.0227 (12)0.0015 (9)0.0051 (9)0.0049 (9)
C30.0165 (12)0.0135 (12)0.0210 (12)0.0017 (9)0.0066 (9)0.0021 (9)
C40.0214 (13)0.0173 (12)0.0200 (12)0.0027 (10)0.0083 (10)0.0007 (10)
C50.0276 (14)0.0259 (14)0.0152 (12)0.0025 (11)0.0075 (10)0.0005 (10)
C60.0241 (13)0.0195 (13)0.0148 (11)0.0025 (10)0.0023 (9)0.0048 (9)
C70.0173 (12)0.0150 (12)0.0158 (11)0.0027 (9)0.0032 (9)0.0018 (9)
C80.0171 (12)0.0168 (12)0.0190 (12)0.0001 (10)0.0022 (9)0.0060 (9)
C90.0288 (14)0.0313 (15)0.0197 (12)0.0084 (12)0.0045 (10)0.0089 (11)
C100.0263 (14)0.0323 (15)0.0231 (13)0.0001 (12)0.0089 (11)0.0130 (11)
C110.0162 (12)0.0177 (12)0.0185 (12)0.0055 (10)0.0061 (9)0.0059 (9)
C120.0215 (13)0.0194 (12)0.0170 (11)0.0075 (10)0.0059 (9)0.0069 (10)
C130.0325 (15)0.0266 (14)0.0172 (12)0.0061 (12)0.0072 (10)0.0065 (10)
C140.0403 (16)0.0309 (15)0.0133 (12)0.0062 (13)0.0000 (11)0.0016 (11)
C150.0259 (14)0.0217 (13)0.0201 (12)0.0034 (11)0.0039 (10)0.0004 (10)
C160.0173 (12)0.0169 (12)0.0196 (12)0.0059 (10)0.0016 (9)0.0023 (9)
C170.0134 (12)0.0149 (12)0.0251 (13)0.0037 (9)0.0001 (9)0.0020 (10)
C180.0179 (13)0.0268 (14)0.0315 (14)0.0017 (11)0.0002 (11)0.0029 (11)
C190.0167 (12)0.0189 (12)0.0187 (12)0.0073 (10)0.0039 (9)0.0052 (10)
C200.0160 (12)0.0214 (13)0.0315 (14)0.0038 (10)0.0018 (10)0.0063 (11)
C210.0204 (13)0.0248 (14)0.0258 (13)0.0041 (11)0.0043 (10)0.0001 (11)
C220.0315 (15)0.0288 (15)0.0203 (13)0.0084 (12)0.0010 (11)0.0069 (11)
C230.0267 (14)0.0200 (13)0.0228 (13)0.0012 (11)0.0042 (10)0.0089 (10)
C240.0205 (13)0.0160 (12)0.0208 (12)0.0026 (10)0.0020 (10)0.0024 (10)
C250.089 (3)0.045 (2)0.0248 (16)0.0015 (19)0.0071 (16)0.0143 (14)
C260.051 (2)0.069 (2)0.0218 (15)0.0097 (18)0.0086 (14)0.0023 (15)
C270.0177 (12)0.0152 (12)0.0159 (11)0.0033 (9)0.0041 (9)0.0061 (9)
C280.0187 (12)0.0181 (12)0.0184 (12)0.0005 (10)0.0003 (9)0.0027 (9)
C290.0137 (12)0.0223 (13)0.0257 (13)0.0003 (10)0.0014 (10)0.0075 (10)
C300.0166 (12)0.0178 (12)0.0251 (13)0.0025 (10)0.0044 (10)0.0052 (10)
C310.0194 (13)0.0185 (13)0.0228 (12)0.0002 (10)0.0034 (10)0.0006 (10)
C320.0141 (12)0.0184 (12)0.0227 (12)0.0012 (10)0.0002 (9)0.0024 (10)
C330.0181 (13)0.0281 (15)0.0461 (17)0.0025 (11)0.0130 (12)0.0063 (12)
C340.0282 (15)0.0335 (16)0.0377 (16)0.0062 (13)0.0125 (12)0.0069 (13)
C350.0160 (12)0.0174 (12)0.0180 (11)0.0004 (9)0.0039 (9)0.0067 (9)
C360.0150 (12)0.0209 (13)0.0233 (12)0.0023 (10)0.0066 (10)0.0071 (10)
C370.0216 (13)0.0198 (13)0.0200 (12)0.0014 (10)0.0044 (10)0.0035 (10)
C380.0183 (12)0.0208 (13)0.0218 (12)0.0003 (10)0.0021 (10)0.0110 (10)
C390.0142 (12)0.0293 (14)0.0235 (13)0.0013 (10)0.0040 (10)0.0092 (11)
C400.0204 (13)0.0209 (13)0.0227 (12)0.0033 (10)0.0072 (10)0.0059 (10)
C410.0326 (16)0.0252 (15)0.0342 (15)0.0025 (12)0.0014 (12)0.0004 (12)
C420.0250 (14)0.0355 (16)0.0325 (15)0.0094 (12)0.0036 (11)0.0063 (12)
C430.0146 (12)0.0171 (12)0.0212 (12)0.0031 (10)0.0024 (9)0.0038 (9)
C440.0176 (13)0.0209 (13)0.0311 (14)0.0012 (10)0.0041 (10)0.0115 (11)
C450.0165 (12)0.0219 (13)0.0325 (14)0.0037 (10)0.0083 (10)0.0081 (11)
C460.0214 (13)0.0195 (13)0.0249 (13)0.0016 (10)0.0063 (10)0.0069 (10)
C470.0224 (13)0.0183 (13)0.0272 (13)0.0029 (10)0.0043 (10)0.0083 (10)
C480.0181 (12)0.0177 (12)0.0274 (13)0.0008 (10)0.0061 (10)0.0046 (10)
C490.0318 (15)0.0338 (16)0.0254 (14)0.0011 (12)0.0087 (11)0.0034 (12)
C500.057 (2)0.055 (2)0.0333 (16)0.0227 (17)0.0205 (15)0.0239 (15)
Ni20.01312 (15)0.01556 (15)0.01360 (14)0.00094 (12)0.00360 (11)0.00327 (11)
N110.0140 (10)0.0143 (10)0.0187 (10)0.0005 (8)0.0050 (8)0.0027 (8)
N120.0142 (10)0.0142 (10)0.0172 (10)0.0002 (8)0.0041 (8)0.0024 (8)
N130.0147 (10)0.0192 (10)0.0187 (10)0.0014 (8)0.0032 (8)0.0068 (8)
N140.0130 (10)0.0167 (10)0.0196 (10)0.0016 (8)0.0053 (8)0.0035 (8)
N150.0124 (10)0.0175 (10)0.0159 (9)0.0040 (8)0.0032 (7)0.0044 (8)
N160.0159 (10)0.0173 (10)0.0222 (10)0.0014 (8)0.0026 (8)0.0061 (8)
N170.0173 (11)0.0253 (12)0.0309 (12)0.0039 (9)0.0101 (9)0.0022 (9)
N180.0465 (15)0.0418 (15)0.0183 (11)0.0026 (12)0.0030 (10)0.0106 (10)
N190.0212 (11)0.0263 (12)0.0224 (11)0.0051 (9)0.0002 (9)0.0041 (9)
N200.0332 (13)0.0223 (12)0.0254 (11)0.0000 (10)0.0118 (9)0.0038 (9)
C510.0314 (15)0.0311 (15)0.0215 (13)0.0138 (12)0.0076 (11)0.0112 (11)
C520.0172 (12)0.0156 (12)0.0194 (12)0.0002 (10)0.0040 (9)0.0046 (9)
C530.0178 (12)0.0147 (12)0.0181 (11)0.0019 (9)0.0048 (9)0.0033 (9)
C540.0244 (13)0.0229 (13)0.0171 (12)0.0028 (11)0.0044 (10)0.0039 (10)
C550.0278 (14)0.0286 (14)0.0163 (12)0.0024 (11)0.0099 (10)0.0023 (10)
C560.0199 (13)0.0195 (13)0.0236 (13)0.0042 (10)0.0094 (10)0.0022 (10)
C570.0146 (12)0.0144 (12)0.0218 (12)0.0002 (9)0.0051 (9)0.0030 (9)
C580.0132 (11)0.0157 (12)0.0221 (12)0.0005 (9)0.0055 (9)0.0038 (9)
C590.0224 (13)0.0250 (14)0.0263 (13)0.0071 (11)0.0072 (10)0.0057 (11)
C600.0246 (14)0.0296 (14)0.0243 (13)0.0021 (11)0.0082 (10)0.0105 (11)
C610.0133 (12)0.0210 (13)0.0196 (12)0.0026 (10)0.0077 (9)0.0053 (10)
C620.0175 (12)0.0194 (12)0.0199 (12)0.0052 (10)0.0061 (9)0.0044 (10)
C630.0255 (14)0.0281 (14)0.0187 (12)0.0050 (11)0.0085 (10)0.0043 (10)
C640.0323 (15)0.0339 (15)0.0150 (12)0.0057 (12)0.0032 (11)0.0017 (11)
C650.0219 (13)0.0254 (14)0.0219 (13)0.0015 (11)0.0013 (10)0.0007 (10)
C660.0149 (12)0.0174 (12)0.0209 (12)0.0051 (10)0.0014 (9)0.0036 (10)
C670.0125 (11)0.0160 (12)0.0235 (12)0.0023 (9)0.0007 (9)0.0036 (10)
C680.0175 (13)0.0248 (14)0.0265 (13)0.0025 (11)0.0027 (10)0.0036 (11)
C690.0157 (12)0.0174 (12)0.0155 (11)0.0028 (9)0.0042 (9)0.0059 (9)
C700.0191 (12)0.0196 (13)0.0199 (12)0.0006 (10)0.0031 (10)0.0015 (10)
C710.0128 (12)0.0221 (13)0.0246 (13)0.0006 (10)0.0006 (9)0.0064 (10)
C720.0186 (12)0.0182 (12)0.0217 (12)0.0012 (10)0.0059 (10)0.0080 (10)
C730.0169 (12)0.0183 (12)0.0199 (12)0.0001 (10)0.0032 (9)0.0012 (10)
C740.0147 (12)0.0197 (12)0.0196 (12)0.0004 (10)0.0016 (9)0.0036 (10)
C750.0180 (13)0.0260 (14)0.0443 (16)0.0040 (11)0.0097 (12)0.0114 (12)
C760.0277 (15)0.0309 (15)0.0306 (14)0.0078 (12)0.0118 (11)0.0010 (12)
C770.0144 (12)0.0205 (13)0.0183 (11)0.0063 (10)0.0051 (9)0.0057 (10)
C780.0187 (12)0.0189 (13)0.0205 (12)0.0023 (10)0.0018 (10)0.0023 (10)
C790.0259 (14)0.0205 (13)0.0236 (13)0.0008 (11)0.0045 (10)0.0080 (10)
C800.0276 (14)0.0248 (14)0.0192 (12)0.0072 (11)0.0022 (10)0.0057 (10)
C810.0210 (13)0.0257 (14)0.0250 (13)0.0022 (11)0.0047 (10)0.0019 (11)
C820.0142 (12)0.0212 (13)0.0294 (13)0.0007 (10)0.0027 (10)0.0074 (10)
C830.075 (3)0.063 (2)0.0260 (16)0.014 (2)0.0068 (16)0.0183 (15)
C840.061 (2)0.055 (2)0.0230 (15)0.0020 (18)0.0058 (14)0.0063 (14)
C850.0156 (12)0.0180 (12)0.0193 (12)0.0011 (10)0.0029 (9)0.0061 (9)
C860.0200 (13)0.0224 (13)0.0229 (12)0.0021 (10)0.0066 (10)0.0040 (10)
C870.0156 (12)0.0271 (14)0.0255 (13)0.0014 (10)0.0031 (10)0.0066 (11)
C880.0205 (13)0.0217 (13)0.0182 (12)0.0034 (10)0.0006 (9)0.0104 (10)
C890.0216 (13)0.0206 (13)0.0192 (12)0.0001 (10)0.0054 (10)0.0029 (10)
C900.0145 (12)0.0232 (13)0.0218 (12)0.0004 (10)0.0064 (9)0.0069 (10)
C910.0217 (14)0.0330 (16)0.0327 (15)0.0094 (12)0.0023 (11)0.0077 (12)
C920.0334 (16)0.0322 (16)0.0245 (14)0.0057 (13)0.0006 (11)0.0001 (11)
C930.0154 (12)0.0170 (12)0.0196 (12)0.0051 (10)0.0014 (9)0.0029 (9)
C940.0178 (13)0.0235 (14)0.0324 (14)0.0021 (10)0.0033 (10)0.0128 (11)
C950.0180 (13)0.0249 (14)0.0369 (15)0.0049 (11)0.0104 (11)0.0077 (11)
C960.0221 (13)0.0166 (12)0.0230 (12)0.0057 (10)0.0046 (10)0.0009 (10)
C970.0247 (14)0.0196 (13)0.0280 (13)0.0013 (11)0.0025 (11)0.0093 (10)
C980.0176 (12)0.0185 (13)0.0280 (13)0.0036 (10)0.0052 (10)0.0078 (10)
C990.0399 (17)0.0326 (16)0.0302 (15)0.0022 (13)0.0150 (13)0.0001 (12)
C1000.0505 (19)0.0433 (18)0.0288 (15)0.0067 (15)0.0130 (13)0.0142 (13)
Cl10.0372 (4)0.0388 (4)0.0420 (4)0.0156 (3)0.0163 (3)0.0197 (3)
Cl20.0301 (3)0.0307 (4)0.0248 (3)0.0085 (3)0.0075 (3)0.0091 (3)
Cl30.0377 (4)0.0244 (3)0.0230 (3)0.0058 (3)0.0118 (3)0.0037 (3)
Cl40.0318 (3)0.0256 (3)0.0227 (3)0.0056 (3)0.0119 (3)0.0043 (2)
C1S0.0398 (17)0.0360 (17)0.0377 (16)0.0043 (14)0.0036 (13)0.0143 (13)
Cl50.0444 (5)0.0626 (6)0.0497 (5)0.0157 (4)0.0080 (4)0.0278 (4)
Cl60.0417 (4)0.0436 (4)0.0466 (4)0.0194 (4)0.0126 (3)0.0136 (4)
C2S0.065 (2)0.0424 (19)0.0442 (18)0.0049 (17)0.0361 (17)0.0097 (15)
Cl70.0575 (5)0.0495 (5)0.0516 (5)0.0051 (4)0.0162 (4)0.0146 (4)
Cl80.0694 (6)0.0399 (5)0.0447 (5)0.0032 (4)0.0117 (4)0.0145 (4)
C3S0.0442 (18)0.0299 (16)0.0341 (15)0.0086 (13)0.0093 (13)0.0107 (12)
Cl90.0470 (5)0.0439 (4)0.0336 (4)0.0046 (4)0.0058 (3)0.0104 (3)
Cl100.0378 (4)0.0386 (5)0.0687 (6)0.0053 (4)0.0097 (4)0.0011 (4)
C4S0.0419 (18)0.0387 (18)0.0351 (16)0.0035 (14)0.0025 (13)0.0130 (13)
Cl110.0483 (5)0.0393 (4)0.0457 (4)0.0161 (4)0.0162 (4)0.0152 (3)
Cl120.0410 (5)0.0649 (6)0.0500 (5)0.0092 (4)0.0063 (4)0.0249 (4)
O10.0311 (11)0.0299 (11)0.0288 (10)0.0007 (9)0.0081 (8)0.0037 (8)
O20.0390 (12)0.0301 (11)0.0309 (10)0.0060 (9)0.0106 (9)0.0035 (8)
O30.0683 (15)0.0297 (11)0.0323 (11)0.0198 (11)0.0264 (10)0.0110 (9)
O40.0944 (19)0.0404 (13)0.0651 (15)0.0388 (13)0.0599 (15)0.0272 (12)
Geometric parameters (Å, º) top
Ni1—N21.9694 (18)N14—C611.285 (3)
Ni1—N51.9725 (18)N14—C851.422 (3)
Ni1—N32.0844 (18)N15—C621.331 (3)
Ni1—N42.0948 (19)N15—C661.334 (3)
Ni1—N12.1243 (19)N16—C671.280 (3)
Ni1—N62.1354 (19)N16—C931.427 (3)
N1—C21.277 (3)N17—C721.388 (3)
N1—C191.432 (3)N17—C761.445 (3)
N2—C71.338 (3)N17—C751.451 (3)
N2—C31.340 (3)N18—C801.382 (3)
N3—C81.286 (3)N18—C831.434 (4)
N3—C271.421 (3)N18—C841.441 (4)
N4—C111.284 (3)N19—C881.381 (3)
N4—C351.423 (3)N19—C911.450 (3)
N5—C121.328 (3)N19—C921.452 (3)
N5—C161.336 (3)N20—C961.386 (3)
N6—C171.281 (3)N20—C1001.447 (3)
N6—C431.429 (3)N20—C991.458 (3)
N7—C221.376 (3)C51—C521.489 (3)
N7—C251.436 (4)C51—H51A0.9800
N7—C261.437 (4)C51—H51B0.9800
N8—C301.372 (3)C51—H51C0.9800
N8—C341.434 (3)C52—C531.489 (3)
N8—C331.443 (3)C53—C541.382 (3)
N9—C381.377 (3)C54—C551.382 (3)
N9—C411.451 (3)C54—H540.9500
N9—C421.456 (3)C55—C561.388 (3)
N10—C461.376 (3)C55—H550.9500
N10—C501.434 (3)C56—C571.379 (3)
N10—C491.450 (3)C56—H560.9500
C1—C21.494 (3)C57—C581.489 (3)
C1—H1A0.9800C58—C591.490 (3)
C1—H1B0.9800C59—H59A0.9800
C1—H1C0.9800C59—H59B0.9800
C2—C31.489 (3)C59—H59C0.9800
C3—C41.380 (3)C60—C611.493 (3)
C4—C51.387 (3)C60—H60A0.9800
C4—H40.9500C60—H60B0.9800
C5—C61.384 (3)C60—H60C0.9800
C5—H50.9500C61—C621.484 (3)
C6—C71.386 (3)C62—C631.384 (3)
C6—H60.9500C63—C641.379 (4)
C7—C81.486 (3)C63—H630.9500
C8—C91.485 (3)C64—C651.382 (4)
C9—H9A0.9800C64—H640.9500
C9—H9B0.9800C65—C661.382 (3)
C9—H9C0.9800C65—H650.9500
C10—C111.491 (3)C66—C671.488 (3)
C10—H10A0.9800C67—C681.489 (3)
C10—H10B0.9800C68—H68A0.9800
C10—H10C0.9800C68—H68B0.9800
C11—C121.486 (3)C68—H68C0.9800
C12—C131.383 (3)C69—C741.384 (3)
C13—C141.383 (4)C69—C701.387 (3)
C13—H130.9500C70—C711.377 (3)
C14—C151.381 (4)C70—H700.9500
C14—H140.9500C71—C721.398 (3)
C15—C161.383 (3)C71—H710.9500
C15—H150.9500C72—C731.400 (3)
C16—C171.482 (3)C73—C741.379 (3)
C17—C181.488 (3)C73—H730.9500
C18—H18A0.9800C74—H740.9500
C18—H18B0.9800C75—H75A0.9800
C18—H18C0.9800C75—H75B0.9800
C19—C241.377 (3)C75—H75C0.9800
C19—C201.389 (3)C76—H76A0.9800
C20—C211.377 (3)C76—H76B0.9800
C20—H200.9500C76—H76C0.9800
C21—C221.405 (4)C77—C781.373 (3)
C21—H210.9500C77—C821.390 (3)
C22—C231.398 (3)C78—C791.383 (3)
C23—C241.384 (3)C78—H780.9500
C23—H230.9500C79—C801.401 (3)
C24—H240.9500C79—H790.9500
C25—H25A0.9800C80—C811.403 (4)
C25—H25B0.9800C81—C821.373 (3)
C25—H25C0.9800C81—H810.9500
C26—H26A0.9800C82—H820.9500
C26—H26B0.9800C83—H83A0.9800
C26—H26C0.9800C83—H83B0.9800
C27—C321.383 (3)C83—H83C0.9800
C27—C281.387 (3)C84—H84A0.9800
C28—C291.373 (3)C84—H84B0.9800
C28—H280.9500C84—H84C0.9800
C29—C301.402 (3)C85—C861.386 (3)
C29—H290.9500C85—C901.387 (3)
C30—C311.403 (3)C86—C871.375 (3)
C31—C321.376 (3)C86—H860.9500
C31—H310.9500C87—C881.404 (3)
C32—H320.9500C87—H870.9500
C33—H33A0.9800C88—C891.405 (3)
C33—H33B0.9800C89—C901.379 (3)
C33—H33C0.9800C89—H890.9500
C34—H34A0.9800C90—H900.9500
C34—H34B0.9800C91—H91A0.9800
C34—H34C0.9800C91—H91B0.9800
C35—C361.381 (3)C91—H91C0.9800
C35—C401.390 (3)C92—H92A0.9800
C36—C371.379 (3)C92—H92B0.9800
C36—H360.9500C92—H92C0.9800
C37—C381.406 (3)C93—C941.379 (3)
C37—H370.9500C93—C981.384 (3)
C38—C391.404 (3)C94—C951.378 (3)
C39—C401.376 (3)C94—H940.9500
C39—H390.9500C95—C961.400 (3)
C40—H400.9500C95—H950.9500
C41—H41A0.9800C96—C971.396 (3)
C41—H41B0.9800C97—C981.377 (3)
C41—H41C0.9800C97—H970.9500
C42—H42A0.9800C98—H980.9500
C42—H42B0.9800C99—H99A0.9800
C42—H42C0.9800C99—H99B0.9800
C43—C441.378 (3)C99—H99C0.9800
C43—C481.386 (3)C100—H10D0.9800
C44—C451.377 (3)C100—H10E0.9800
C44—H440.9500C100—H10F0.9800
C45—C461.401 (3)C1S—Cl51.761 (3)
C45—H450.9500C1S—Cl61.762 (3)
C46—C471.400 (3)C1S—H1SA0.9900
C47—C481.377 (3)C1S—H1SB0.9900
C47—H470.9500C2S—Cl81.754 (3)
C48—H480.9500C2S—Cl71.804 (3)
C49—H49A0.9800C2S—H2SA0.9900
C49—H49B0.9800C2S—H2SB0.9900
C49—H49C0.9800C3S—Cl101.747 (3)
C50—H50A0.9800C3S—Cl91.768 (3)
C50—H50B0.9800C3S—H3SA0.9900
C50—H50C0.9800C3S—H3SB0.9900
Ni2—N121.9658 (18)C4S—Cl121.757 (3)
Ni2—N151.9711 (18)C4S—Cl111.762 (3)
Ni2—N142.0909 (19)C4S—H4SA0.9900
Ni2—N112.0977 (19)C4S—H4SB0.9900
Ni2—N132.1188 (19)O1—H1OA0.9059
Ni2—N162.141 (2)O1—H1OB0.8792
N11—C521.281 (3)O2—H2OA1.0124
N11—C691.424 (3)O2—H2OB0.9488
N12—C531.331 (3)O3—H3OA0.8977
N12—C571.338 (3)O3—H3OB0.8681
N13—C581.281 (3)O4—H4OA0.9400
N13—C771.432 (3)O4—H4OB1.0754
N2—Ni1—N5167.57 (8)N13—Ni2—N1693.21 (7)
N2—Ni1—N377.92 (7)C52—N11—C69122.23 (19)
N5—Ni1—N3111.32 (7)C52—N11—Ni2114.90 (15)
N2—Ni1—N4110.91 (7)C69—N11—Ni2122.67 (14)
N5—Ni1—N477.83 (8)C53—N12—C57121.22 (19)
N3—Ni1—N492.14 (7)C53—N12—Ni2117.99 (15)
N2—Ni1—N176.66 (7)C57—N12—Ni2118.85 (15)
N5—Ni1—N194.65 (7)C58—N13—C77123.3 (2)
N3—Ni1—N1153.98 (7)C58—N13—Ni2115.75 (15)
N4—Ni1—N191.75 (7)C77—N13—Ni2120.70 (14)
N2—Ni1—N694.89 (7)C61—N14—C85120.50 (19)
N5—Ni1—N676.68 (8)C61—N14—Ni2114.47 (15)
N3—Ni1—N693.36 (7)C85—N14—Ni2125.02 (14)
N4—Ni1—N6154.19 (7)C62—N15—C66121.43 (19)
N1—Ni1—N694.25 (7)C62—N15—Ni2118.25 (16)
C2—N1—C19123.0 (2)C66—N15—Ni2119.56 (15)
C2—N1—Ni1115.82 (15)C67—N16—C93122.8 (2)
C19—N1—Ni1120.76 (14)C67—N16—Ni2114.91 (16)
C7—N2—C3121.08 (19)C93—N16—Ni2121.82 (14)
C7—N2—Ni1117.70 (15)C72—N17—C76119.4 (2)
C3—N2—Ni1118.99 (15)C72—N17—C75119.1 (2)
C8—N3—C27121.54 (19)C76—N17—C75115.2 (2)
C8—N3—Ni1115.05 (15)C80—N18—C83118.1 (2)
C27—N3—Ni1123.16 (14)C80—N18—C84118.2 (2)
C11—N4—C35120.56 (19)C83—N18—C84117.8 (2)
C11—N4—Ni1114.91 (16)C88—N19—C91118.9 (2)
C35—N4—Ni1124.53 (14)C88—N19—C92118.0 (2)
C12—N5—C16121.6 (2)C91—N19—C92114.2 (2)
C12—N5—Ni1118.15 (16)C96—N20—C100118.0 (2)
C16—N5—Ni1119.28 (16)C96—N20—C99117.7 (2)
C17—N6—C43123.4 (2)C100—N20—C99114.8 (2)
C17—N6—Ni1115.06 (16)C52—C51—H51A109.5
C43—N6—Ni1121.40 (14)C52—C51—H51B109.5
C22—N7—C25120.1 (2)H51A—C51—H51B109.5
C22—N7—C26120.6 (3)C52—C51—H51C109.5
C25—N7—C26119.2 (2)H51A—C51—H51C109.5
C30—N8—C34120.0 (2)H51B—C51—H51C109.5
C30—N8—C33120.6 (2)N11—C52—C51126.4 (2)
C34—N8—C33118.1 (2)N11—C52—C53114.9 (2)
C38—N9—C41118.4 (2)C51—C52—C53118.7 (2)
C38—N9—C42118.8 (2)N12—C53—C54121.0 (2)
C41—N9—C42114.8 (2)N12—C53—C52112.90 (19)
C46—N10—C50119.4 (2)C54—C53—C52126.1 (2)
C46—N10—C49119.4 (2)C53—C54—C55118.4 (2)
C50—N10—C49118.1 (2)C53—C54—H54120.8
C2—C1—H1A109.5C55—C54—H54120.8
C2—C1—H1B109.5C54—C55—C56120.2 (2)
H1A—C1—H1B109.5C54—C55—H55119.9
C2—C1—H1C109.5C56—C55—H55119.9
H1A—C1—H1C109.5C57—C56—C55118.2 (2)
H1B—C1—H1C109.5C57—C56—H56120.9
N1—C2—C3114.3 (2)C55—C56—H56120.9
N1—C2—C1125.9 (2)N12—C57—C56121.0 (2)
C3—C2—C1119.8 (2)N12—C57—C58113.09 (19)
N2—C3—C4121.0 (2)C56—C57—C58125.9 (2)
N2—C3—C2112.76 (19)N13—C58—C57114.1 (2)
C4—C3—C2126.2 (2)N13—C58—C59125.8 (2)
C3—C4—C5118.1 (2)C57—C58—C59120.1 (2)
C3—C4—H4120.9C58—C59—H59A109.5
C5—C4—H4120.9C58—C59—H59B109.5
C6—C5—C4120.7 (2)H59A—C59—H59B109.5
C6—C5—H5119.7C58—C59—H59C109.5
C4—C5—H5119.7H59A—C59—H59C109.5
C5—C6—C7118.0 (2)H59B—C59—H59C109.5
C5—C6—H6121.0C61—C60—H60A109.5
C7—C6—H6121.0C61—C60—H60B109.5
N2—C7—C6121.0 (2)H60A—C60—H60B109.5
N2—C7—C8112.55 (19)C61—C60—H60C109.5
C6—C7—C8126.4 (2)H60A—C60—H60C109.5
N3—C8—C9126.2 (2)H60B—C60—H60C109.5
N3—C8—C7115.0 (2)N14—C61—C62115.5 (2)
C9—C8—C7118.7 (2)N14—C61—C60126.2 (2)
C8—C9—H9A109.5C62—C61—C60118.2 (2)
C8—C9—H9B109.5N15—C62—C63120.7 (2)
H9A—C9—H9B109.5N15—C62—C61113.01 (19)
C8—C9—H9C109.5C63—C62—C61126.2 (2)
H9A—C9—H9C109.5C64—C63—C62118.3 (2)
H9B—C9—H9C109.5C64—C63—H63120.9
C11—C10—H10A109.5C62—C63—H63120.9
C11—C10—H10B109.5C63—C64—C65120.5 (2)
H10A—C10—H10B109.5C63—C64—H64119.8
C11—C10—H10C109.5C65—C64—H64119.8
H10A—C10—H10C109.5C64—C65—C66118.3 (2)
H10B—C10—H10C109.5C64—C65—H65120.9
N4—C11—C12114.9 (2)C66—C65—H65120.9
N4—C11—C10126.9 (2)N15—C66—C65120.7 (2)
C12—C11—C10118.1 (2)N15—C66—C67113.43 (19)
N5—C12—C13120.5 (2)C65—C66—C67125.8 (2)
N5—C12—C11113.50 (19)N16—C67—C66114.8 (2)
C13—C12—C11126.0 (2)N16—C67—C68126.2 (2)
C12—C13—C14118.7 (2)C66—C67—C68118.9 (2)
C12—C13—H13120.7C67—C68—H68A109.5
C14—C13—H13120.7C67—C68—H68B109.5
C15—C14—C13120.0 (2)H68A—C68—H68B109.5
C15—C14—H14120.0C67—C68—H68C109.5
C13—C14—H14120.0H68A—C68—H68C109.5
C14—C15—C16118.5 (2)H68B—C68—H68C109.5
C14—C15—H15120.7C74—C69—C70118.5 (2)
C16—C15—H15120.7C74—C69—N11119.0 (2)
N5—C16—C15120.6 (2)C70—C69—N11122.3 (2)
N5—C16—C17113.43 (19)C71—C70—C69120.9 (2)
C15—C16—C17126.0 (2)C71—C70—H70119.6
N6—C17—C16114.8 (2)C69—C70—H70119.6
N6—C17—C18126.1 (2)C70—C71—C72121.1 (2)
C16—C17—C18119.1 (2)C70—C71—H71119.4
C17—C18—H18A109.5C72—C71—H71119.4
C17—C18—H18B109.5N17—C72—C71121.9 (2)
H18A—C18—H18B109.5N17—C72—C73120.5 (2)
C17—C18—H18C109.5C71—C72—C73117.6 (2)
H18A—C18—H18C109.5C74—C73—C72120.8 (2)
H18B—C18—H18C109.5C74—C73—H73119.6
C24—C19—C20119.3 (2)C72—C73—H73119.6
C24—C19—N1119.3 (2)C73—C74—C69121.1 (2)
C20—C19—N1120.5 (2)C73—C74—H74119.4
C21—C20—C19120.5 (2)C69—C74—H74119.4
C21—C20—H20119.7N17—C75—H75A109.5
C19—C20—H20119.7N17—C75—H75B109.5
C20—C21—C22120.8 (2)H75A—C75—H75B109.5
C20—C21—H21119.6N17—C75—H75C109.5
C22—C21—H21119.6H75A—C75—H75C109.5
N7—C22—C23120.7 (2)H75B—C75—H75C109.5
N7—C22—C21121.4 (2)N17—C76—H76A109.5
C23—C22—C21117.9 (2)N17—C76—H76B109.5
C24—C23—C22120.7 (2)H76A—C76—H76B109.5
C24—C23—H23119.6N17—C76—H76C109.5
C22—C23—H23119.6H76A—C76—H76C109.5
C19—C24—C23120.7 (2)H76B—C76—H76C109.5
C19—C24—H24119.6C78—C77—C82119.0 (2)
C23—C24—H24119.6C78—C77—N13119.4 (2)
N7—C25—H25A109.5C82—C77—N13120.6 (2)
N7—C25—H25B109.5C77—C78—C79121.0 (2)
H25A—C25—H25B109.5C77—C78—H78119.5
N7—C25—H25C109.5C79—C78—H78119.5
H25A—C25—H25C109.5C78—C79—C80120.8 (2)
H25B—C25—H25C109.5C78—C79—H79119.6
N7—C26—H26A109.5C80—C79—H79119.6
N7—C26—H26B109.5N18—C80—C79120.0 (2)
H26A—C26—H26B109.5N18—C80—C81122.6 (2)
N7—C26—H26C109.5C79—C80—C81117.4 (2)
H26A—C26—H26C109.5C82—C81—C80121.1 (2)
H26B—C26—H26C109.5C82—C81—H81119.4
C32—C27—C28118.5 (2)C80—C81—H81119.4
C32—C27—N3119.5 (2)C81—C82—C77120.7 (2)
C28—C27—N3121.9 (2)C81—C82—H82119.7
C29—C28—C27121.3 (2)C77—C82—H82119.7
C29—C28—H28119.4N18—C83—H83A109.5
C27—C28—H28119.4N18—C83—H83B109.5
C28—C29—C30120.7 (2)H83A—C83—H83B109.5
C28—C29—H29119.6N18—C83—H83C109.5
C30—C29—H29119.6H83A—C83—H83C109.5
N8—C30—C29121.5 (2)H83B—C83—H83C109.5
N8—C30—C31121.0 (2)N18—C84—H84A109.5
C29—C30—C31117.5 (2)N18—C84—H84B109.5
C32—C31—C30121.1 (2)H84A—C84—H84B109.5
C32—C31—H31119.5N18—C84—H84C109.5
C30—C31—H31119.5H84A—C84—H84C109.5
C31—C32—C27120.8 (2)H84B—C84—H84C109.5
C31—C32—H32119.6C86—C85—C90118.7 (2)
C27—C32—H32119.6C86—C85—N14121.3 (2)
N8—C33—H33A109.5C90—C85—N14120.0 (2)
N8—C33—H33B109.5C87—C86—C85121.0 (2)
H33A—C33—H33B109.5C87—C86—H86119.5
N8—C33—H33C109.5C85—C86—H86119.5
H33A—C33—H33C109.5C86—C87—C88121.2 (2)
H33B—C33—H33C109.5C86—C87—H87119.4
N8—C34—H34A109.5C88—C87—H87119.4
N8—C34—H34B109.5N19—C88—C87121.1 (2)
H34A—C34—H34B109.5N19—C88—C89121.8 (2)
N8—C34—H34C109.5C87—C88—C89117.1 (2)
H34A—C34—H34C109.5C90—C89—C88121.2 (2)
H34B—C34—H34C109.5C90—C89—H89119.4
C36—C35—C40118.9 (2)C88—C89—H89119.4
C36—C35—N4120.1 (2)C89—C90—C85120.8 (2)
C40—C35—N4121.0 (2)C89—C90—H90119.6
C37—C36—C35120.9 (2)C85—C90—H90119.6
C37—C36—H36119.5N19—C91—H91A109.5
C35—C36—H36119.5N19—C91—H91B109.5
C36—C37—C38121.2 (2)H91A—C91—H91B109.5
C36—C37—H37119.4N19—C91—H91C109.5
C38—C37—H37119.4H91A—C91—H91C109.5
N9—C38—C39121.3 (2)H91B—C91—H91C109.5
N9—C38—C37121.7 (2)N19—C92—H92A109.5
C39—C38—C37116.9 (2)N19—C92—H92B109.5
C40—C39—C38121.6 (2)H92A—C92—H92B109.5
C40—C39—H39119.2N19—C92—H92C109.5
C38—C39—H39119.2H92A—C92—H92C109.5
C39—C40—C35120.5 (2)H92B—C92—H92C109.5
C39—C40—H40119.7C94—C93—C98118.3 (2)
C35—C40—H40119.7C94—C93—N16121.3 (2)
N9—C41—H41A109.5C98—C93—N16119.8 (2)
N9—C41—H41B109.5C95—C94—C93120.9 (2)
H41A—C41—H41B109.5C95—C94—H94119.5
N9—C41—H41C109.5C93—C94—H94119.5
H41A—C41—H41C109.5C94—C95—C96121.7 (2)
H41B—C41—H41C109.5C94—C95—H95119.2
N9—C42—H42A109.5C96—C95—H95119.2
N9—C42—H42B109.5N20—C96—C97122.2 (2)
H42A—C42—H42B109.5N20—C96—C95121.4 (2)
N9—C42—H42C109.5C97—C96—C95116.4 (2)
H42A—C42—H42C109.5C98—C97—C96121.7 (2)
H42B—C42—H42C109.5C98—C97—H97119.2
C44—C43—C48118.5 (2)C96—C97—H97119.2
C44—C43—N6121.2 (2)C97—C98—C93120.9 (2)
C48—C43—N6119.5 (2)C97—C98—H98119.5
C45—C44—C43121.0 (2)C93—C98—H98119.5
C45—C44—H44119.5N20—C99—H99A109.5
C43—C44—H44119.5N20—C99—H99B109.5
C44—C45—C46121.4 (2)H99A—C99—H99B109.5
C44—C45—H45119.3N20—C99—H99C109.5
C46—C45—H45119.3H99A—C99—H99C109.5
N10—C46—C47121.7 (2)H99B—C99—H99C109.5
N10—C46—C45121.5 (2)N20—C100—H10D109.5
C47—C46—C45116.8 (2)N20—C100—H10E109.5
C48—C47—C46121.3 (2)H10D—C100—H10E109.5
C48—C47—H47119.4N20—C100—H10F109.5
C46—C47—H47119.4H10D—C100—H10F109.5
C47—C48—C43120.9 (2)H10E—C100—H10F109.5
C47—C48—H48119.5Cl5—C1S—Cl6110.65 (16)
C43—C48—H48119.5Cl5—C1S—H1SA109.5
N10—C49—H49A109.5Cl6—C1S—H1SA109.5
N10—C49—H49B109.5Cl5—C1S—H1SB109.5
H49A—C49—H49B109.5Cl6—C1S—H1SB109.5
N10—C49—H49C109.5H1SA—C1S—H1SB108.1
H49A—C49—H49C109.5Cl8—C2S—Cl7109.50 (16)
H49B—C49—H49C109.5Cl8—C2S—H2SA109.8
N10—C50—H50A109.5Cl7—C2S—H2SA109.8
N10—C50—H50B109.5Cl8—C2S—H2SB109.8
H50A—C50—H50B109.5Cl7—C2S—H2SB109.8
N10—C50—H50C109.5H2SA—C2S—H2SB108.2
H50A—C50—H50C109.5Cl10—C3S—Cl9112.50 (15)
H50B—C50—H50C109.5Cl10—C3S—H3SA109.1
N12—Ni2—N15167.94 (8)Cl9—C3S—H3SA109.1
N12—Ni2—N14110.67 (7)Cl10—C3S—H3SB109.1
N15—Ni2—N1478.01 (7)Cl9—C3S—H3SB109.1
N12—Ni2—N1177.79 (7)H3SA—C3S—H3SB107.8
N15—Ni2—N11111.03 (7)Cl12—C4S—Cl11110.70 (16)
N14—Ni2—N1191.70 (7)Cl12—C4S—H4SA109.5
N12—Ni2—N1376.89 (7)Cl11—C4S—H4SA109.5
N15—Ni2—N1394.86 (7)Cl12—C4S—H4SB109.5
N14—Ni2—N1391.88 (7)Cl11—C4S—H4SB109.5
N11—Ni2—N13154.04 (7)H4SA—C4S—H4SB108.1
N12—Ni2—N1694.74 (7)H1OA—O1—H1OB101.9
N15—Ni2—N1676.75 (8)H2OA—O2—H2OB106.9
N14—Ni2—N16154.58 (7)H3OA—O3—H3OB107.3
N11—Ni2—N1694.50 (7)H4OA—O4—H4OB97.4
C19—N1—C2—C3174.7 (2)C69—N11—C52—C518.0 (4)
Ni1—N1—C2—C31.7 (3)Ni2—N11—C52—C51177.1 (2)
C19—N1—C2—C16.6 (4)C69—N11—C52—C53174.92 (19)
Ni1—N1—C2—C1179.59 (18)Ni2—N11—C52—C530.0 (3)
C7—N2—C3—C40.9 (3)C57—N12—C53—C540.7 (3)
Ni1—N2—C3—C4163.54 (17)Ni2—N12—C53—C54164.72 (18)
C7—N2—C3—C2176.91 (19)C57—N12—C53—C52178.1 (2)
Ni1—N2—C3—C214.3 (2)Ni2—N12—C53—C5214.1 (2)
N1—C2—C3—N29.9 (3)N11—C52—C53—N128.8 (3)
C1—C2—C3—N2171.3 (2)C51—C52—C53—N12173.9 (2)
N1—C2—C3—C4167.8 (2)N11—C52—C53—C54170.0 (2)
C1—C2—C3—C411.0 (4)C51—C52—C53—C547.4 (4)
N2—C3—C4—C51.4 (3)N12—C53—C54—C550.2 (4)
C2—C3—C4—C5176.1 (2)C52—C53—C54—C55178.8 (2)
C3—C4—C5—C61.0 (4)C53—C54—C55—C560.2 (4)
C4—C5—C6—C70.1 (4)C54—C55—C56—C570.6 (4)
C3—N2—C7—C60.0 (3)C53—N12—C57—C561.6 (3)
Ni1—N2—C7—C6162.83 (17)Ni2—N12—C57—C56165.45 (17)
C3—N2—C7—C8177.9 (2)C53—N12—C57—C58177.1 (2)
Ni1—N2—C7—C815.1 (2)Ni2—N12—C57—C5813.2 (3)
C5—C6—C7—N20.4 (3)C55—C56—C57—N121.5 (3)
C5—C6—C7—C8178.0 (2)C55—C56—C57—C58177.0 (2)
C27—N3—C8—C98.4 (4)C77—N13—C58—C57173.8 (2)
Ni1—N3—C8—C9177.17 (19)Ni2—N13—C58—C570.4 (3)
C27—N3—C8—C7173.92 (19)C77—N13—C58—C597.6 (4)
Ni1—N3—C8—C70.5 (3)Ni2—N13—C58—C59178.22 (18)
N2—C7—C8—N39.1 (3)N12—C57—C58—N137.8 (3)
C6—C7—C8—N3168.6 (2)C56—C57—C58—N13170.8 (2)
N2—C7—C8—C9173.1 (2)N12—C57—C58—C59173.4 (2)
C6—C7—C8—C99.2 (4)C56—C57—C58—C598.0 (4)
C35—N4—C11—C12173.98 (19)C85—N14—C61—C62173.63 (19)
Ni1—N4—C11—C126.3 (2)Ni2—N14—C61—C627.3 (2)
C35—N4—C11—C1010.6 (3)C85—N14—C61—C6011.3 (3)
Ni1—N4—C11—C10169.21 (19)Ni2—N14—C61—C60167.74 (19)
C16—N5—C12—C133.5 (3)C66—N15—C62—C633.5 (3)
Ni1—N5—C12—C13172.13 (17)Ni2—N15—C62—C63173.47 (17)
C16—N5—C12—C11175.21 (19)C66—N15—C62—C61175.69 (19)
Ni1—N5—C12—C116.6 (3)Ni2—N15—C62—C615.7 (3)
N4—C11—C12—N50.2 (3)N14—C61—C62—N151.5 (3)
C10—C11—C12—N5175.7 (2)C60—C61—C62—N15174.0 (2)
N4—C11—C12—C13178.8 (2)N14—C61—C62—C63179.4 (2)
C10—C11—C12—C132.9 (3)C60—C61—C62—C635.1 (3)
N5—C12—C13—C141.1 (4)N15—C62—C63—C640.3 (4)
C11—C12—C13—C14177.5 (2)C61—C62—C63—C64178.7 (2)
C12—C13—C14—C151.7 (4)C62—C63—C64—C652.1 (4)
C13—C14—C15—C162.0 (4)C63—C64—C65—C661.6 (4)
C12—N5—C16—C153.1 (3)C62—N15—C66—C654.0 (3)
Ni1—N5—C16—C15171.65 (17)Ni2—N15—C66—C65173.90 (17)
C12—N5—C16—C17175.3 (2)C62—N15—C66—C67173.76 (19)
Ni1—N5—C16—C176.8 (3)Ni2—N15—C66—C673.9 (3)
C14—C15—C16—N50.3 (3)C64—C65—C66—N151.4 (3)
C14—C15—C16—C17177.9 (2)C64—C65—C66—C67176.0 (2)
C43—N6—C17—C16178.06 (19)C93—N16—C67—C66178.7 (2)
Ni1—N6—C17—C166.1 (2)Ni2—N16—C67—C666.6 (2)
C43—N6—C17—C184.2 (4)C93—N16—C67—C681.7 (4)
Ni1—N6—C17—C18171.64 (19)Ni2—N16—C67—C68170.43 (18)
N5—C16—C17—N60.0 (3)N15—C66—C67—N162.2 (3)
C15—C16—C17—N6178.4 (2)C65—C66—C67—N16179.8 (2)
N5—C16—C17—C18177.9 (2)N15—C66—C67—C68175.1 (2)
C15—C16—C17—C180.5 (4)C65—C66—C67—C682.6 (3)
C2—N1—C19—C2484.7 (3)C52—N11—C69—C74130.9 (2)
Ni1—N1—C19—C2487.9 (2)Ni2—N11—C69—C7454.5 (3)
C2—N1—C19—C20106.2 (3)C52—N11—C69—C7054.3 (3)
Ni1—N1—C19—C2081.2 (2)Ni2—N11—C69—C70120.3 (2)
C24—C19—C20—C210.2 (3)C74—C69—C70—C710.9 (3)
N1—C19—C20—C21168.9 (2)N11—C69—C70—C71175.7 (2)
C19—C20—C21—C220.6 (4)C69—C70—C71—C720.1 (4)
C25—N7—C22—C232.9 (4)C76—N17—C72—C71168.5 (2)
C26—N7—C22—C23173.3 (3)C75—N17—C72—C7117.6 (3)
C25—N7—C22—C21176.1 (3)C76—N17—C72—C7313.7 (3)
C26—N7—C22—C217.6 (4)C75—N17—C72—C73164.6 (2)
C20—C21—C22—N7177.5 (3)C70—C71—C72—N17178.1 (2)
C20—C21—C22—C231.5 (4)C70—C71—C72—C730.3 (3)
N7—C22—C23—C24177.4 (2)N17—C72—C73—C74177.4 (2)
C21—C22—C23—C241.7 (4)C71—C72—C73—C740.4 (3)
C20—C19—C24—C230.1 (3)C72—C73—C74—C691.4 (4)
N1—C19—C24—C23169.1 (2)C70—C69—C74—C731.7 (3)
C22—C23—C24—C190.9 (4)N11—C69—C74—C73176.7 (2)
C8—N3—C27—C32130.6 (2)C58—N13—C77—C7886.4 (3)
Ni1—N3—C27—C3255.5 (3)Ni2—N13—C77—C7887.6 (2)
C8—N3—C27—C2853.9 (3)C58—N13—C77—C82105.1 (3)
Ni1—N3—C27—C28120.1 (2)Ni2—N13—C77—C8281.0 (2)
C32—C27—C28—C291.0 (3)C82—C77—C78—C790.6 (3)
N3—C27—C28—C29176.6 (2)N13—C77—C78—C79168.2 (2)
C27—C28—C29—C300.9 (4)C77—C78—C79—C800.2 (4)
C34—N8—C30—C29174.7 (2)C83—N18—C80—C7925.9 (4)
C33—N8—C30—C298.3 (4)C84—N18—C80—C79178.5 (3)
C34—N8—C30—C314.8 (4)C83—N18—C80—C81154.1 (3)
C33—N8—C30—C31171.2 (2)C84—N18—C80—C811.4 (4)
C28—C29—C30—N8178.9 (2)C78—C79—C80—N18178.9 (2)
C28—C29—C30—C311.6 (3)C78—C79—C80—C811.0 (4)
N8—C30—C31—C32179.9 (2)N18—C80—C81—C82178.7 (2)
C29—C30—C31—C320.4 (4)C79—C80—C81—C821.2 (4)
C30—C31—C32—C271.5 (4)C80—C81—C82—C770.5 (4)
C28—C27—C32—C312.2 (3)C78—C77—C82—C810.4 (3)
N3—C27—C32—C31177.9 (2)N13—C77—C82—C81168.2 (2)
C11—N4—C35—C36129.5 (2)C61—N14—C85—C8653.4 (3)
Ni1—N4—C35—C3650.3 (3)Ni2—N14—C85—C86127.7 (2)
C11—N4—C35—C4053.0 (3)C61—N14—C85—C90128.8 (2)
Ni1—N4—C35—C40127.2 (2)Ni2—N14—C85—C9050.1 (3)
C40—C35—C36—C372.4 (3)C90—C85—C86—C871.8 (4)
N4—C35—C36—C37180.0 (2)N14—C85—C86—C87179.5 (2)
C35—C36—C37—C382.2 (4)C85—C86—C87—C880.6 (4)
C41—N9—C38—C39170.1 (2)C91—N19—C88—C8719.4 (3)
C42—N9—C38—C3923.0 (3)C92—N19—C88—C87164.9 (2)
C41—N9—C38—C3713.3 (3)C91—N19—C88—C89162.7 (2)
C42—N9—C38—C37160.4 (2)C92—N19—C88—C8917.2 (3)
C36—C37—C38—N9175.8 (2)C86—C87—C88—N19177.7 (2)
C36—C37—C38—C390.9 (3)C86—C87—C88—C890.3 (3)
N9—C38—C39—C40176.7 (2)N19—C88—C89—C90176.7 (2)
C37—C38—C39—C400.0 (3)C87—C88—C89—C901.2 (3)
C38—C39—C40—C350.3 (4)C88—C89—C90—C852.5 (4)
C36—C35—C40—C391.5 (3)C86—C85—C90—C892.7 (3)
N4—C35—C40—C39179.0 (2)N14—C85—C90—C89179.5 (2)
C17—N6—C43—C4489.2 (3)C67—N16—C93—C9481.9 (3)
Ni1—N6—C43—C4486.4 (2)Ni2—N16—C93—C9489.7 (2)
C17—N6—C43—C48101.2 (3)C67—N16—C93—C98107.3 (3)
Ni1—N6—C43—C4883.2 (2)Ni2—N16—C93—C9881.2 (2)
C48—C43—C44—C451.2 (4)C98—C93—C94—C951.0 (4)
N6—C43—C44—C45168.5 (2)N16—C93—C94—C95170.0 (2)
C43—C44—C45—C460.4 (4)C93—C94—C95—C960.5 (4)
C50—N10—C46—C478.6 (4)C100—N20—C96—C977.7 (4)
C49—N10—C46—C47168.5 (2)C99—N20—C96—C97152.2 (2)
C50—N10—C46—C45172.0 (3)C100—N20—C96—C95174.5 (2)
C49—N10—C46—C4512.1 (4)C99—N20—C96—C9530.0 (3)
C44—C45—C46—N10179.5 (2)C94—C95—C96—N20179.9 (2)
C44—C45—C46—C471.1 (4)C94—C95—C96—C972.2 (4)
N10—C46—C47—C48178.8 (2)N20—C96—C97—C98179.6 (2)
C45—C46—C47—C481.8 (4)C95—C96—C97—C982.5 (4)
C46—C47—C48—C431.0 (4)C96—C97—C98—C931.2 (4)
C44—C43—C48—C470.6 (4)C94—C93—C98—C970.7 (4)
N6—C43—C48—C47169.4 (2)N16—C93—C98—C97170.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1OA···Cl10.912.333.2381 (19)177
O1—H1OB···Cl20.882.313.188 (2)177
O2—H2OA···Cl11.012.183.192 (2)175
O2—H2OB···Cl20.952.323.2691 (19)177
O3—H3OA···Cl40.902.303.198 (2)178
O3—H3OB···Cl30.872.343.201 (2)174
O4—H4OB···Cl31.082.123.180 (2)168
O4—H4OA···Cl40.942.253.192 (2)177
C1S—H1SB···Cl30.992.473.422 (3)162
C2S—H2SA···Cl40.992.813.743 (4)158
C2S—H2SB···Cl1i0.992.663.642 (3)169
C3S—H3SA···N17ii0.992.423.403 (4)173
C3S—H3SB···Cl20.992.493.447 (3)163
C4S—H4SA···Cl40.992.543.527 (3)176
Symmetry codes: (i) x, y+1, z; (ii) x1, y, z.
Interplanar angles and close ππ interactions (Å, °) top
Phenyl ringPyridine ringAngle
C19–C24N2–C787.58 (6)
C27–C28N2–C764.85 (7)
C35–C40N5–C1654.42 (8)
C43–C48N5–C1683.76 (6)
C69–C74N12–C5763.47 (7)
C77–C82N12–C5787.83 (6)
C85–C90N15–C6653.63 (8)
C93–C98N15–C6681.53 (7)
Phenyl ringPyridine ringCg1···Cg2
C43–C48N2–C73.487 (1)
C19–C24N5–C463.675 (1)
C93–C98N12–C573.520 (1)
C85–C90N15–C663.696 (1)
Cg1 and Cg2 are the centroids for the named phenyl and pyridine rings.
 

Acknowledgements

The authors thank Professor Christopher Dunlap and all of the undergraduate students in the Advanced Lab at Saint Mary's College.

References

First citationBabbini, D. C. & Iluc, V. M. (2015). Organometallics, 34, 3141–3151.  Web of Science CSD CrossRef CAS Google Scholar
First citationBruin, B. de, Bill, E., Bothe, E., Weyhermüller, T. & Wieghardt, K. (2000). Inorg. Chem. 39, 2936–2947.  Web of Science PubMed Google Scholar
First citationBruker. (2016). APEX3 and SAINT. Bruker AXS Inc. Madison, Wisconsin, USA.  Google Scholar
First citationCason, C. J. (2003). POV-RAY. Persistence of Vision Raytracer Pty. Ltd, Victoria, Australia.  Google Scholar
First citationChen, Y., Chen, R., Qian, C., Dong, X. & Sun, J. (2003). Organometallics, 22, 4312–4321.  Web of Science CSD CrossRef CAS Google Scholar
First citationChirik, P. J. & Wieghardt, K. (2010). Science, 327, 794–795.  Web of Science CrossRef CAS PubMed Google Scholar
First citationGroom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationHaneline, M. R. & Heyduk, A. F. (2006). J. Am. Chem. Soc. 128, 8410–8411.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationKrause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3–10.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationLyaskovskyy, V. & de Bruin, B. (2012). ACS Catal. 2, 270–279.  CrossRef CAS Google Scholar
First citationMacrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationPatel, R. N., Shukla, K. K., Singh, A., Choudhary, M., Patel, D. K., Niclós-Gutiérrez, J. & Choquesillo-Lazarte, D. (2010). J. Coord. Chem. 63, 3648–3661.  Web of Science CSD CrossRef CAS Google Scholar
First citationPraneeth, V. K., Ringenberg, M. R. & Ward, T. R. (2012). Angew. Chem. Int. Ed. 51, 10228–10234.  Web of Science CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSmall, B. L. & Brookhart, M. (1999). Macromolecules, 32, 2120–2130.  Web of Science CSD CrossRef CAS Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSu, B. & Feng, G. (2010). Polym. Int. 59, 1058–1063.  CAS Google Scholar
First citationTrivedi, M., Pandey, D. S. & Xu, Q. (2007). Inorg. Chim. Acta, 360, 2492–2498.  Web of Science CSD CrossRef CAS Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds