metal-organic compounds
Aquabis(2,2′-bipyridine-κ2N,N′)chloridonickel(II) chloride chloroform monosolvate hemihydrate
aDepartment of Chemistry and Biochemistry, Florida International University, 11200 SW 8th Street, Miami, FL 33199, USA, and bDepartment of Chemistry, Aristotle University of Thessaloniki, University Campus, Thessaloniki, 54124, Greece
*Correspondence e-mail: logesh.mathivathanan@fiu.edu
The title solvated salt, [NiCl(C10H8N2)2(H2O)]Cl·CHCl3·0.5H2O, contains a mononuclear NiII complex cation with 2,2′-bipyridine, chloride and aqua ligands forming a slightly distorted ClN4O octahedral coordination set. The charge of the cation is balanced by a chloride anion. In the crystal, half a water molecule and a chloroform solvent molecule are present per formula unit. Individual components are held together by O—H⋯Cl hydrogen bonding and π–π interactions.
CCDC reference: 1517485
Structure description
The NiII cation has a distorted octahedral coordination environment with the chlorido and aqua ligands in a cis configuration relative to each other (Fig. 1). The two N,N′-bipyridine ligands are almost perpendicular to each other [dihedral angle 88.73 (16)°]. The Ni—N distances range between 2.059 (3) and 2.102 (3) Å, while the Ni—O(water) and Ni—Cl distances are 2.084 (3) and 2.418 (1) Å, respectively. Similar cis-[MIICl(2,2′-bipy)2(H2O)]+ cations are known for M = Mn (Chen et al., 1995) and Cd (Lei & Li, 2011). A few [NiLL′)2Cl(OHR)]+ complexes are known in the literature where LL′ is a bidentate chelating N-donor ligand such as 2,2′-bipyridine or 1,10-phenanthroline. Examples with R = H or methyl were given by Brewer et al. (2003) and Chesnut et al. (1999). Interestingly, all except one adopt the cis-configuration. The trans-configuration between Cl and H2O is known for a tetradentate bis-phenanthroline ligand, viz., 2,2′-bis-(1,10-phenanthroline) (Rice & Anderson, 2000), where presumably prevents a cis configuration. In one case, [Ni(2,2′-bipy)2Cl(OH2)]+ has been formed in situ by reacting [Ni(2,2′-bipy)3]2+ with Cl− and H2O. The reaction was concentration-sensitive and the [Ni(2,2′-bipy)Cl(OH2)]+ cation forms a three-dimensional hydrogen-bonded network with deprotonated benzene tetracarboxylic acid moieties (Sun et al., 2010).
The 3 solvent molecule and a lattice water molecule located on a twofold rotation axis. The Ni-bound water (O1) molecule forms weak hydrogen bonds with the Cl− counter-anion (Cl5) and the coordinating Cl (Cl1) atom from an adjacent molecule (Table 1, Fig. 2). Although the H atoms of the lattice water molecule could not be located, O⋯Cl distances of 3.231 (3) Å to the counter-anion indicate likewise weak hydrogen bonding. π–π interactions between the pyridyl rings of parallel-stacked 2,2-bipy molecules [C11—C13 = 3.465 (6) Å] are also present in the (Fig. 3). It is worth noting that similar Cl-bridged hetero- and homo-binuclear compounds dominate NiCl2(LL')2-chemistry. One example of such heterobinuclear compound, [Ni(2,2′-bipy)2(μ-Cl)2CdI2], has been reported (Chesnut et al., 1999).
of the title compound also contains a CHClSynthesis and crystallization
The title compound was isolated when 2,2′-bipyridine was used as an auxiliary ligand for the intended preparation of a Ni-sulfonamide complex. A solution of NiCl2·6H2O (34.2 mg, 0.144 mmol) in 10 ml MeOH was added slowly to a solution of N,N-diphenyl-1,2-benzenesulfonamide (60 mg, 0.144 mmol) and 2,2′-bipyridine (25.5 mg, 0.163 mmol) in 8 ml MeOH and 2.2 eq. of NHEt2, at room temperature. A precipitate formed after 10 min and the reaction was stirred for an additional three hours. The precipitate was filtered off the methanol solution; the yellow–green precipitate was collected and crystals were obtained by diffusion of diethyl ether vapor into a chloroform solution of the compound.
Refinement
Crystal data, data collection and structure . The hydrogen atoms of the lattice water molecule could not be modelled satisfactorily and were omitted from the but are included in the formula.
details are summarized in Table 2Structural data
CCDC reference: 1517485
https://doi.org/10.1107/S2414314616018344/wm5333sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616018344/wm5333Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314616018344/wm5333Isup3.cdx
Data collection: APEX3 (Bruker, 2015); cell
SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015); program(s) used to refine structure: ShelXle (Hübschle et al., 2011) and OLEX2 (Dolomanov et al., 2009); molecular graphics: ShelXle (Hübschle et al., 2011); software used to prepare material for publication: publCIF (Westrip et al., 2010).[NiCl(C10H8N2)2(H2O)]Cl·CHCl3·0.5H2O | F(000) = 2392 |
Mr = 588.36 | Dx = 1.572 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 29.1709 (14) Å | Cell parameters from 9884 reflections |
b = 11.2898 (5) Å | θ = 2.8–26.3° |
c = 20.0517 (10) Å | µ = 1.34 mm−1 |
β = 131.163 (1)° | T = 300 K |
V = 4971.5 (4) Å3 | Trapezoid, blue |
Z = 8 | 0.14 × 0.07 × 0.06 mm |
Bruker D8 Quest CMOS diffractometer | 3870 reflections with I > 2σ(I) |
ω and φ scans | Rint = 0.048 |
Absorption correction: multi-scan (SADABS; Bruker, 2015) | θmax = 26.5°, θmin = 2.8° |
Tmin = 0.692, Tmax = 0.745 | h = −36→36 |
42949 measured reflections | k = −14→14 |
5141 independent reflections | l = −25→25 |
Refinement on F2 | 2 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.052 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.140 | w = 1/[σ2(Fo2) + (0.0585P)2 + 19.6746P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
5141 reflections | Δρmax = 0.56 e Å−3 |
300 parameters | Δρmin = −0.71 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 | ||
Ni1 | 0.41761 (2) | 0.23752 (4) | 0.55719 (3) | 0.02914 (15) | |
Cl1 | 0.52576 (4) | 0.27540 (10) | 0.66856 (6) | 0.0436 (3) | |
O1 | 0.42085 (15) | 0.1520 (3) | 0.65230 (19) | 0.0481 (8) | |
N1 | 0.32221 (14) | 0.2227 (3) | 0.4674 (2) | 0.0329 (7) | |
N2 | 0.39253 (14) | 0.3961 (3) | 0.5772 (2) | 0.0329 (7) | |
N3 | 0.41843 (14) | 0.3077 (3) | 0.4617 (2) | 0.0372 (8) | |
N4 | 0.42689 (14) | 0.0861 (3) | 0.5098 (2) | 0.0387 (8) | |
C1 | 0.33271 (17) | 0.4149 (3) | 0.5258 (2) | 0.0315 (8) | |
C2 | 0.3104 (2) | 0.5186 (4) | 0.5327 (3) | 0.0444 (10) | |
H2 | 0.2687 | 0.5299 | 0.4980 | 0.053* | |
C3 | 0.3508 (2) | 0.6044 (4) | 0.5916 (3) | 0.0532 (12) | |
H3 | 0.3367 | 0.6746 | 0.5968 | 0.064* | |
C4 | 0.4116 (2) | 0.5858 (4) | 0.6421 (3) | 0.0494 (11) | |
H4 | 0.4395 | 0.6435 | 0.6816 | 0.059* | |
C5 | 0.4311 (2) | 0.4808 (4) | 0.6340 (3) | 0.0437 (10) | |
H5 | 0.4727 | 0.4678 | 0.6694 | 0.052* | |
C6 | 0.29276 (16) | 0.3194 (3) | 0.4628 (2) | 0.0313 (8) | |
C7 | 0.23009 (18) | 0.3261 (4) | 0.4031 (3) | 0.0443 (10) | |
H7 | 0.2106 | 0.3939 | 0.3997 | 0.053* | |
C8 | 0.1965 (2) | 0.2306 (4) | 0.3481 (3) | 0.0497 (11) | |
H8 | 0.1542 | 0.2334 | 0.3077 | 0.060* | |
C9 | 0.22615 (19) | 0.1322 (4) | 0.3538 (3) | 0.0482 (11) | |
H9 | 0.2044 | 0.0667 | 0.3180 | 0.058* | |
C10 | 0.28837 (18) | 0.1316 (4) | 0.4131 (3) | 0.0427 (10) | |
H10 | 0.3083 | 0.0648 | 0.4159 | 0.051* | |
C11 | 0.42223 (18) | 0.1021 (4) | 0.4384 (3) | 0.0451 (11) | |
C12 | 0.4180 (2) | 0.0055 (6) | 0.3914 (4) | 0.0672 (15) | |
H12 | 0.4138 | 0.0173 | 0.3417 | 0.081* | |
C13 | 0.4201 (3) | −0.1054 (6) | 0.4185 (5) | 0.0789 (18) | |
H13 | 0.4173 | −0.1702 | 0.3874 | 0.095* | |
C14 | 0.4263 (2) | −0.1229 (5) | 0.4919 (4) | 0.0718 (16) | |
H14 | 0.4281 | −0.1989 | 0.5113 | 0.086* | |
C15 | 0.4298 (2) | −0.0244 (4) | 0.5363 (3) | 0.0520 (11) | |
H15 | 0.4343 | −0.0355 | 0.5863 | 0.062* | |
C16 | 0.42170 (18) | 0.2267 (4) | 0.4160 (3) | 0.0450 (11) | |
C17 | 0.4276 (2) | 0.2633 (6) | 0.3550 (3) | 0.0692 (16) | |
H17 | 0.4304 | 0.2072 | 0.3237 | 0.083* | |
C18 | 0.4294 (3) | 0.3796 (7) | 0.3418 (4) | 0.0792 (19) | |
H18 | 0.4330 | 0.4040 | 0.3012 | 0.095* | |
C19 | 0.4259 (2) | 0.4610 (6) | 0.3881 (3) | 0.0709 (16) | |
H19 | 0.4274 | 0.5415 | 0.3800 | 0.085* | |
C20 | 0.4200 (2) | 0.4220 (4) | 0.4472 (3) | 0.0516 (11) | |
H20 | 0.4170 | 0.4779 | 0.4783 | 0.062* | |
H1A | 0.402 (2) | 0.088 (3) | 0.646 (3) | 0.062* | |
H1B | 0.4432 (19) | 0.182 (4) | 0.7055 (18) | 0.062* | |
Cl2 | 0.28738 (15) | 0.61538 (18) | 0.34457 (16) | 0.1420 (10) | |
Cl3 | 0.23219 (9) | 0.83353 (17) | 0.25316 (11) | 0.1017 (6) | |
Cl4 | 0.28069 (7) | 0.80694 (13) | 0.43133 (10) | 0.0766 (4) | |
C21 | 0.2434 (3) | 0.7354 (5) | 0.3311 (4) | 0.0801 (17) | |
H21 | 0.2039 | 0.7064 | 0.3091 | 0.096* | |
Cl5 | 0.36460 (5) | −0.08254 (10) | 0.65231 (8) | 0.0556 (3) | |
O2 | 0.5000 | 0.8219 (5) | 0.7500 | 0.127 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0288 (3) | 0.0340 (3) | 0.0255 (2) | 0.0032 (2) | 0.0182 (2) | 0.0000 (2) |
Cl1 | 0.0293 (5) | 0.0628 (7) | 0.0319 (5) | 0.0040 (4) | 0.0172 (4) | 0.0056 (5) |
O1 | 0.064 (2) | 0.0492 (18) | 0.0373 (16) | −0.0183 (15) | 0.0359 (16) | −0.0078 (14) |
N1 | 0.0319 (16) | 0.0323 (17) | 0.0328 (16) | 0.0022 (13) | 0.0206 (15) | 0.0001 (13) |
N2 | 0.0335 (17) | 0.0348 (17) | 0.0306 (16) | −0.0012 (14) | 0.0212 (15) | −0.0038 (13) |
N3 | 0.0319 (17) | 0.051 (2) | 0.0259 (16) | −0.0028 (15) | 0.0178 (15) | 0.0018 (15) |
N4 | 0.0329 (18) | 0.044 (2) | 0.0405 (19) | 0.0055 (14) | 0.0249 (16) | −0.0013 (15) |
C1 | 0.038 (2) | 0.0300 (19) | 0.0320 (19) | 0.0023 (16) | 0.0256 (18) | 0.0021 (15) |
C2 | 0.047 (2) | 0.041 (2) | 0.046 (2) | 0.0100 (19) | 0.031 (2) | 0.0027 (19) |
C3 | 0.075 (3) | 0.036 (2) | 0.058 (3) | 0.004 (2) | 0.048 (3) | −0.005 (2) |
C4 | 0.063 (3) | 0.041 (2) | 0.046 (3) | −0.013 (2) | 0.037 (2) | −0.014 (2) |
C5 | 0.043 (2) | 0.046 (2) | 0.040 (2) | −0.0075 (19) | 0.026 (2) | −0.0091 (19) |
C6 | 0.034 (2) | 0.034 (2) | 0.0308 (19) | 0.0052 (16) | 0.0230 (17) | 0.0041 (15) |
C7 | 0.034 (2) | 0.048 (3) | 0.046 (2) | 0.0063 (19) | 0.024 (2) | 0.002 (2) |
C8 | 0.029 (2) | 0.063 (3) | 0.045 (2) | −0.002 (2) | 0.019 (2) | −0.003 (2) |
C9 | 0.038 (2) | 0.048 (3) | 0.045 (2) | −0.012 (2) | 0.022 (2) | −0.013 (2) |
C10 | 0.039 (2) | 0.037 (2) | 0.047 (2) | −0.0012 (18) | 0.026 (2) | −0.0074 (19) |
C11 | 0.033 (2) | 0.068 (3) | 0.038 (2) | 0.001 (2) | 0.025 (2) | −0.010 (2) |
C12 | 0.063 (3) | 0.085 (4) | 0.070 (3) | −0.007 (3) | 0.051 (3) | −0.031 (3) |
C13 | 0.075 (4) | 0.075 (4) | 0.104 (5) | −0.002 (3) | 0.066 (4) | −0.036 (4) |
C14 | 0.064 (3) | 0.049 (3) | 0.108 (5) | 0.011 (2) | 0.059 (4) | −0.008 (3) |
C15 | 0.050 (3) | 0.051 (3) | 0.061 (3) | 0.011 (2) | 0.039 (2) | 0.000 (2) |
C16 | 0.032 (2) | 0.075 (3) | 0.028 (2) | 0.000 (2) | 0.0200 (18) | −0.002 (2) |
C17 | 0.066 (3) | 0.112 (5) | 0.044 (3) | −0.004 (3) | 0.043 (3) | −0.006 (3) |
C18 | 0.076 (4) | 0.123 (6) | 0.049 (3) | −0.010 (4) | 0.045 (3) | 0.017 (3) |
C19 | 0.065 (3) | 0.086 (4) | 0.048 (3) | −0.017 (3) | 0.032 (3) | 0.015 (3) |
C20 | 0.051 (3) | 0.061 (3) | 0.037 (2) | −0.008 (2) | 0.027 (2) | 0.004 (2) |
Cl2 | 0.261 (3) | 0.0811 (13) | 0.1370 (18) | 0.0660 (16) | 0.154 (2) | 0.0285 (12) |
Cl3 | 0.1164 (14) | 0.0971 (13) | 0.0744 (10) | 0.0275 (11) | 0.0554 (11) | 0.0225 (9) |
Cl4 | 0.0888 (10) | 0.0663 (9) | 0.0773 (9) | 0.0039 (8) | 0.0557 (9) | −0.0023 (7) |
C21 | 0.079 (4) | 0.073 (4) | 0.082 (4) | 0.000 (3) | 0.050 (4) | −0.003 (3) |
Cl5 | 0.0589 (7) | 0.0393 (6) | 0.0658 (7) | 0.0008 (5) | 0.0398 (6) | 0.0006 (5) |
O2 | 0.064 (4) | 0.053 (4) | 0.170 (7) | 0.000 | 0.036 (4) | 0.000 |
Ni1—N4 | 2.059 (3) | C7—H7 | 0.9300 |
Ni1—N2 | 2.071 (3) | C8—C9 | 1.365 (6) |
Ni1—O1 | 2.084 (3) | C8—H8 | 0.9300 |
Ni1—N3 | 2.087 (3) | C9—C10 | 1.366 (6) |
Ni1—N1 | 2.102 (3) | C9—H9 | 0.9300 |
Ni1—Cl1 | 2.4183 (11) | C10—H10 | 0.9300 |
O1—H1A | 0.872 (19) | C11—C12 | 1.393 (6) |
O1—H1B | 0.874 (19) | C11—C16 | 1.473 (7) |
N1—C10 | 1.343 (5) | C12—C13 | 1.351 (9) |
N1—C6 | 1.355 (5) | C12—H12 | 0.9300 |
N2—C1 | 1.336 (5) | C13—C14 | 1.374 (8) |
N2—C5 | 1.338 (5) | C13—H13 | 0.9300 |
N3—C20 | 1.330 (6) | C14—C15 | 1.385 (7) |
N3—C16 | 1.341 (5) | C14—H14 | 0.9300 |
N4—C15 | 1.337 (6) | C15—H15 | 0.9300 |
N4—C11 | 1.357 (5) | C16—C17 | 1.407 (6) |
C1—C2 | 1.390 (5) | C17—C18 | 1.347 (8) |
C1—C6 | 1.476 (5) | C17—H17 | 0.9300 |
C2—C3 | 1.374 (6) | C18—C19 | 1.356 (9) |
C2—H2 | 0.9300 | C18—H18 | 0.9300 |
C3—C4 | 1.361 (7) | C19—C20 | 1.378 (7) |
C3—H3 | 0.9300 | C19—H19 | 0.9300 |
C4—C5 | 1.370 (6) | C20—H20 | 0.9300 |
C4—H4 | 0.9300 | Cl2—C21 | 1.760 (6) |
C5—H5 | 0.9300 | Cl3—C21 | 1.761 (7) |
C6—C7 | 1.378 (5) | Cl4—C21 | 1.731 (6) |
C7—C8 | 1.384 (6) | C21—H21 | 0.9800 |
N4—Ni1—N2 | 167.95 (13) | C6—C7—C8 | 119.2 (4) |
N4—Ni1—O1 | 95.59 (13) | C6—C7—H7 | 120.4 |
N2—Ni1—O1 | 91.87 (12) | C8—C7—H7 | 120.4 |
N4—Ni1—N3 | 78.85 (14) | C9—C8—C7 | 119.4 (4) |
N2—Ni1—N3 | 93.92 (13) | C9—C8—H8 | 120.3 |
O1—Ni1—N3 | 174.13 (13) | C7—C8—H8 | 120.3 |
N4—Ni1—N1 | 92.32 (12) | C8—C9—C10 | 118.8 (4) |
N2—Ni1—N1 | 78.32 (12) | C8—C9—H9 | 120.6 |
O1—Ni1—N1 | 89.09 (12) | C10—C9—H9 | 120.6 |
N3—Ni1—N1 | 93.00 (12) | N1—C10—C9 | 123.2 (4) |
N4—Ni1—Cl1 | 94.88 (9) | N1—C10—H10 | 118.4 |
N2—Ni1—Cl1 | 94.63 (9) | C9—C10—H10 | 118.4 |
O1—Ni1—Cl1 | 89.50 (9) | N4—C11—C12 | 120.8 (5) |
N3—Ni1—Cl1 | 89.10 (9) | N4—C11—C16 | 114.9 (4) |
N1—Ni1—Cl1 | 172.76 (9) | C12—C11—C16 | 124.2 (4) |
Ni1—O1—H1A | 127 (3) | C13—C12—C11 | 119.5 (5) |
Ni1—O1—H1B | 119 (3) | C13—C12—H12 | 120.2 |
H1A—O1—H1B | 114 (5) | C11—C12—H12 | 120.2 |
C10—N1—C6 | 117.9 (3) | C12—C13—C14 | 120.2 (5) |
C10—N1—Ni1 | 127.4 (3) | C12—C13—H13 | 119.9 |
C6—N1—Ni1 | 114.6 (2) | C14—C13—H13 | 119.9 |
C1—N2—C5 | 118.9 (3) | C13—C14—C15 | 118.4 (6) |
C1—N2—Ni1 | 115.9 (2) | C13—C14—H14 | 120.8 |
C5—N2—Ni1 | 125.2 (3) | C15—C14—H14 | 120.8 |
C20—N3—C16 | 119.0 (4) | N4—C15—C14 | 122.3 (5) |
C20—N3—Ni1 | 126.2 (3) | N4—C15—H15 | 118.8 |
C16—N3—Ni1 | 114.6 (3) | C14—C15—H15 | 118.8 |
C15—N4—C11 | 118.7 (4) | N3—C16—C17 | 119.9 (5) |
C15—N4—Ni1 | 125.7 (3) | N3—C16—C11 | 115.7 (4) |
C11—N4—Ni1 | 115.1 (3) | C17—C16—C11 | 124.3 (4) |
N2—C1—C2 | 121.1 (4) | C18—C17—C16 | 120.0 (5) |
N2—C1—C6 | 116.0 (3) | C18—C17—H17 | 120.0 |
C2—C1—C6 | 122.9 (3) | C16—C17—H17 | 120.0 |
C3—C2—C1 | 119.1 (4) | C17—C18—C19 | 119.8 (5) |
C3—C2—H2 | 120.4 | C17—C18—H18 | 120.1 |
C1—C2—H2 | 120.4 | C19—C18—H18 | 120.1 |
C4—C3—C2 | 119.4 (4) | C18—C19—C20 | 118.7 (6) |
C4—C3—H3 | 120.3 | C18—C19—H19 | 120.6 |
C2—C3—H3 | 120.3 | C20—C19—H19 | 120.6 |
C3—C4—C5 | 119.0 (4) | N3—C20—C19 | 122.6 (5) |
C3—C4—H4 | 120.5 | N3—C20—H20 | 118.7 |
C5—C4—H4 | 120.5 | C19—C20—H20 | 118.7 |
N2—C5—C4 | 122.5 (4) | Cl4—C21—Cl2 | 110.1 (4) |
N2—C5—H5 | 118.7 | Cl4—C21—Cl3 | 110.2 (3) |
C4—C5—H5 | 118.7 | Cl2—C21—Cl3 | 108.2 (4) |
N1—C6—C7 | 121.5 (4) | Cl4—C21—H21 | 109.5 |
N1—C6—C1 | 115.0 (3) | Cl2—C21—H21 | 109.5 |
C7—C6—C1 | 123.5 (3) | Cl3—C21—H21 | 109.5 |
C5—N2—C1—C2 | −2.0 (5) | C15—N4—C11—C12 | 2.6 (6) |
Ni1—N2—C1—C2 | −179.4 (3) | Ni1—N4—C11—C12 | −169.8 (3) |
C5—N2—C1—C6 | 178.2 (3) | C15—N4—C11—C16 | −177.7 (4) |
Ni1—N2—C1—C6 | 0.8 (4) | Ni1—N4—C11—C16 | 9.9 (4) |
N2—C1—C2—C3 | 2.0 (6) | N4—C11—C12—C13 | −1.7 (7) |
C6—C1—C2—C3 | −178.3 (4) | C16—C11—C12—C13 | 178.7 (5) |
C1—C2—C3—C4 | −0.4 (7) | C11—C12—C13—C14 | 0.1 (8) |
C2—C3—C4—C5 | −1.1 (7) | C12—C13—C14—C15 | 0.5 (8) |
C1—N2—C5—C4 | 0.5 (6) | C11—N4—C15—C14 | −2.1 (6) |
Ni1—N2—C5—C4 | 177.7 (3) | Ni1—N4—C15—C14 | 169.5 (4) |
C3—C4—C5—N2 | 1.1 (7) | C13—C14—C15—N4 | 0.5 (8) |
C10—N1—C6—C7 | −1.6 (5) | C20—N3—C16—C17 | 1.0 (6) |
Ni1—N1—C6—C7 | 175.9 (3) | Ni1—N3—C16—C17 | −174.8 (3) |
C10—N1—C6—C1 | 178.5 (3) | C20—N3—C16—C11 | 177.6 (4) |
Ni1—N1—C6—C1 | −4.0 (4) | Ni1—N3—C16—C11 | 1.8 (4) |
N2—C1—C6—N1 | 2.2 (5) | N4—C11—C16—N3 | −7.7 (5) |
C2—C1—C6—N1 | −177.6 (4) | C12—C11—C16—N3 | 171.9 (4) |
N2—C1—C6—C7 | −177.7 (4) | N4—C11—C16—C17 | 168.7 (4) |
C2—C1—C6—C7 | 2.5 (6) | C12—C11—C16—C17 | −11.7 (7) |
N1—C6—C7—C8 | 1.7 (6) | N3—C16—C17—C18 | −0.7 (8) |
C1—C6—C7—C8 | −178.4 (4) | C11—C16—C17—C18 | −177.0 (5) |
C6—C7—C8—C9 | −0.4 (7) | C16—C17—C18—C19 | 0.5 (9) |
C7—C8—C9—C10 | −0.9 (7) | C17—C18—C19—C20 | −0.6 (9) |
C6—N1—C10—C9 | 0.2 (6) | C16—N3—C20—C19 | −1.1 (6) |
Ni1—N1—C10—C9 | −177.0 (3) | Ni1—N3—C20—C19 | 174.1 (3) |
C8—C9—C10—N1 | 1.1 (7) | C18—C19—C20—N3 | 0.9 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···Cl5 | 0.87 (2) | 2.25 (2) | 3.115 (3) | 171 (5) |
O1—H1B···Cl1i | 0.87 (2) | 2.30 (2) | 3.148 (3) | 163 (4) |
Symmetry code: (i) −x+1, y, −z+3/2. |
Acknowledgements
REU participant EV was supported by the NSF–REU Site Grant CHE1560375 to FIU.
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