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In the title complex, trans-{2,2′-[cyclo­hexane-1,2-diyl­bis­(ni­t­rilo­methyl­idyne)]­di­phenol­ato-κ4O,N,N′,O′}­nickel(II)–chloro­form (1/1), [Ni(C20H20N2O2)]·CHCl3, the Ni atom has a square-planar geometry, slightly tetrahedrally distorted. The Ni—N and Ni—O bonding distances are within the expected ranges for Ni–Schiff base derivatives. The di­imine bridge has a gauche conformation with the cyclo­hexyl ring almost coplanar with the NiN2O2 plane. The complex mol­ecules pack in dimers with an Ni...Ni distance of 3.59 (1) Å and form a three-dimensional structure displaying a herring-bone configuration. Channels are occupied by solvent mol­ecules, which are involved in C—H...O hydrogen bonds with the ligand O atoms.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100020849/av1056sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100020849/av1056Isup2.hkl
Contains datablock I

CCDC reference: 163886

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: MolEN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (McArdle, 1995); software used to prepare material for publication: SHELXL97.

(I) top
Crystal data top
[Ni(C20H20N2O2)]·CHCl3F(000) = 1024
Mr = 498.46Dx = 1.517 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71069 Å
a = 13.249 (4) ÅCell parameters from 25 reflections
b = 10.086 (9) Åθ = 12–14°
c = 16.695 (5) ŵ = 1.28 mm1
β = 101.99 (2)°T = 293 K
V = 2182 (2) Å3Parallelipedic, orange
Z = 40.2 × 0.04 × 0.03 mm
Data collection top
MACH3-Enraf-Nonius
diffractometer
Rint = 0.033
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 1.8°
Graphite monochromatorh = 1515
ω–2θ scansk = 111
8599 measured reflectionsl = 1919
3839 independent reflections3 standard reflections every 240 reflections
3068 reflections with I > 2σ(I)
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156All H-atom parameters refined
S = 1.06 w = 1/[σ2(Fo2) + (0.079P)2 + 3.473P]
where P = (Fo2 + 2Fc2)/3
3839 reflections(Δ/σ)max = 0.041
346 parametersΔρmax = 0.91 e Å3
0 restraintsΔρmin = 0.78 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.57840 (4)0.87221 (5)0.05649 (3)0.0389 (2)
N10.4614 (3)0.7736 (3)0.05709 (19)0.0431 (7)
N20.5366 (2)0.9797 (3)0.13323 (18)0.0421 (7)
O10.6195 (2)0.7726 (3)0.02338 (17)0.0492 (7)
O20.6996 (2)0.9622 (3)0.05751 (17)0.0540 (7)
C10.4245 (3)0.6807 (4)0.0069 (2)0.0458 (9)
H10.369 (4)0.636 (5)0.011 (3)0.059 (14)*
C110.4675 (3)0.6372 (4)0.0603 (2)0.0424 (8)
C120.4131 (3)0.5442 (4)0.1153 (3)0.0510 (10)
H120.360 (3)0.508 (4)0.103 (2)0.040 (11)*
C130.4488 (4)0.5017 (5)0.1821 (3)0.0595 (11)
H130.406 (4)0.441 (5)0.222 (3)0.065 (14)*
C140.5428 (4)0.5498 (5)0.1934 (3)0.0589 (12)
H140.567 (4)0.518 (5)0.233 (3)0.062 (14)*
C150.5992 (4)0.6379 (4)0.1405 (3)0.0529 (10)
H150.667 (4)0.672 (5)0.148 (3)0.062 (13)*
C160.5628 (3)0.6851 (4)0.0717 (2)0.0432 (9)
C20.5881 (3)1.0763 (4)0.1726 (2)0.0451 (9)
H20.564 (4)1.124 (4)0.215 (3)0.056 (13)*
C210.6878 (3)1.1195 (4)0.1629 (2)0.0454 (9)
C220.7334 (4)1.2289 (4)0.2090 (3)0.0569 (11)
H220.709 (4)1.259 (5)0.245 (3)0.058 (15)*
C230.8222 (4)1.2840 (5)0.1970 (3)0.0664 (13)
H230.844 (4)1.361 (6)0.234 (3)0.082 (17)*
C240.8692 (4)1.2292 (5)0.1380 (3)0.0642 (13)
H240.924 (4)1.271 (6)0.132 (3)0.072 (16)*
C250.8291 (4)1.1215 (5)0.0929 (3)0.0601 (12)
H250.861 (4)1.091 (5)0.051 (3)0.064 (14)*
C260.7364 (3)1.0638 (4)0.1036 (2)0.0468 (9)
C30.4168 (3)0.8033 (4)0.1298 (3)0.0502 (10)
H30.468 (3)0.755 (4)0.185 (2)0.044 (10)*
C80.4302 (3)0.9519 (4)0.1424 (3)0.0508 (10)
H80.381 (3)0.987 (4)0.095 (2)0.043 (10)*
C40.3058 (4)0.7627 (6)0.1256 (3)0.0589 (11)
H410.265 (3)0.803 (5)0.078 (3)0.054 (12)*
H420.302 (5)0.676 (7)0.115 (4)0.10 (2)*
C50.2749 (5)0.8063 (6)0.2053 (4)0.0742 (15)
H510.200 (6)0.802 (8)0.189 (4)0.11 (2)*
H520.327 (4)0.765 (6)0.257 (3)0.078 (16)*
C60.2909 (5)0.9516 (6)0.2213 (4)0.0769 (16)
H610.236 (4)0.988 (6)0.164 (3)0.084 (17)*
H620.273 (5)0.970 (7)0.270 (4)0.10 (2)*
C70.4012 (4)0.9954 (5)0.2214 (3)0.0593 (12)
H710.451 (4)0.962 (5)0.268 (3)0.063 (14)*
H720.404 (5)1.096 (6)0.230 (4)0.090 (18)*
C100.8602 (5)0.7330 (8)0.0288 (4)0.0878 (18)
H100.798 (6)0.773 (7)0.031 (4)0.12 (2)*
Cl10.8514 (3)0.5647 (3)0.0248 (4)0.250 (2)
Cl20.9452 (2)0.7825 (3)0.11647 (16)0.1579 (10)
Cl30.8951 (2)0.8007 (5)0.05408 (15)0.2001 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0433 (3)0.0387 (3)0.0369 (3)0.0015 (2)0.0129 (2)0.00137 (19)
N10.0489 (17)0.0429 (18)0.0399 (16)0.0025 (15)0.0151 (14)0.0008 (14)
N20.0477 (17)0.0401 (17)0.0408 (16)0.0033 (14)0.0144 (13)0.0025 (14)
O10.0490 (15)0.0517 (16)0.0502 (15)0.0065 (13)0.0181 (12)0.0132 (13)
O20.0541 (16)0.0584 (18)0.0524 (16)0.0148 (14)0.0178 (13)0.0155 (14)
C10.044 (2)0.044 (2)0.050 (2)0.0030 (18)0.0109 (17)0.0030 (18)
C110.047 (2)0.037 (2)0.0408 (19)0.0029 (16)0.0040 (16)0.0036 (16)
C120.049 (2)0.044 (2)0.056 (2)0.0013 (19)0.0033 (19)0.0004 (19)
C130.071 (3)0.048 (2)0.054 (2)0.005 (2)0.000 (2)0.012 (2)
C140.077 (3)0.052 (3)0.048 (2)0.009 (2)0.015 (2)0.011 (2)
C150.060 (3)0.052 (2)0.049 (2)0.003 (2)0.018 (2)0.0066 (19)
C160.054 (2)0.0362 (19)0.0401 (19)0.0065 (17)0.0109 (16)0.0001 (16)
C20.056 (2)0.037 (2)0.042 (2)0.0079 (18)0.0094 (17)0.0006 (17)
C210.054 (2)0.035 (2)0.043 (2)0.0061 (17)0.0003 (17)0.0022 (16)
C220.061 (3)0.041 (2)0.063 (3)0.009 (2)0.000 (2)0.006 (2)
C230.066 (3)0.045 (3)0.078 (3)0.003 (2)0.009 (3)0.009 (2)
C240.056 (3)0.058 (3)0.073 (3)0.016 (2)0.001 (2)0.002 (2)
C250.059 (3)0.065 (3)0.057 (3)0.014 (2)0.012 (2)0.002 (2)
C260.051 (2)0.042 (2)0.044 (2)0.0019 (18)0.0026 (17)0.0004 (17)
C30.056 (2)0.050 (2)0.049 (2)0.0016 (19)0.0222 (19)0.0014 (19)
C80.053 (2)0.051 (2)0.053 (2)0.0043 (19)0.021 (2)0.0013 (19)
C40.057 (3)0.066 (3)0.060 (3)0.005 (2)0.026 (2)0.000 (2)
C50.077 (4)0.079 (4)0.081 (4)0.008 (3)0.048 (3)0.003 (3)
C60.081 (4)0.079 (4)0.086 (4)0.003 (3)0.053 (3)0.005 (3)
C70.073 (3)0.054 (3)0.060 (3)0.004 (2)0.034 (2)0.002 (2)
C100.063 (3)0.107 (5)0.096 (4)0.011 (3)0.020 (3)0.002 (4)
Cl10.131 (2)0.1056 (19)0.477 (7)0.0126 (17)0.020 (3)0.024 (3)
Cl20.162 (2)0.166 (2)0.1197 (17)0.0118 (19)0.0312 (15)0.0024 (16)
Cl30.147 (2)0.362 (5)0.1091 (17)0.037 (3)0.0689 (16)0.049 (2)
Geometric parameters (Å, º) top
Ni1—O11.840 (3)C22—H220.80 (5)
Ni1—O21.842 (3)C23—C241.385 (8)
Ni1—N11.844 (3)C23—H231.00 (6)
Ni1—N21.849 (3)C24—C251.364 (7)
N1—C11.284 (5)C24—H240.87 (6)
N1—C31.487 (5)C25—C261.404 (6)
N2—C21.289 (5)C25—H250.95 (5)
N2—C81.475 (5)C3—C41.514 (6)
O1—C161.320 (5)C3—C81.518 (6)
O2—C261.312 (5)C3—H31.14 (4)
C1—C111.429 (6)C8—C71.513 (6)
C1—H10.88 (5)C8—H80.98 (4)
C11—C161.401 (6)C4—C51.536 (7)
C11—C121.402 (6)C4—H410.96 (5)
C12—C131.368 (7)C4—H420.89 (7)
C12—H120.85 (4)C5—C61.497 (9)
C13—C141.386 (7)C5—H510.97 (7)
C13—H130.99 (5)C5—H521.07 (6)
C14—C151.361 (7)C6—C71.526 (7)
C14—H140.86 (5)C6—H611.14 (6)
C15—C161.417 (5)C6—H620.92 (6)
C15—H150.99 (5)C7—H710.97 (5)
C2—C211.432 (6)C7—H721.03 (6)
C2—H20.97 (5)C10—Cl31.690 (7)
C21—C261.405 (6)C10—Cl11.702 (8)
C21—C221.408 (6)C10—Cl21.725 (7)
C22—C231.354 (7)C10—H100.92 (7)
O1—Ni1—O283.53 (13)C23—C24—H24114 (4)
O1—Ni1—N194.87 (13)C24—C25—C26120.7 (5)
O2—Ni1—N1176.78 (14)C24—C25—H25119 (3)
O1—Ni1—N2177.09 (13)C26—C25—H25120 (3)
O2—Ni1—N295.21 (14)O2—C26—C25118.5 (4)
N1—Ni1—N286.52 (14)O2—C26—C21123.8 (4)
C1—N1—C3121.2 (3)C25—C26—C21117.7 (4)
C1—N1—Ni1126.6 (3)N1—C3—C4117.1 (4)
C3—N1—Ni1111.9 (3)N1—C3—C8104.9 (3)
C2—N2—C8120.5 (3)C4—C3—C8111.0 (4)
C2—N2—Ni1126.4 (3)N1—C3—H3108 (2)
C8—N2—Ni1113.0 (3)C4—C3—H3109 (2)
C16—O1—Ni1126.3 (2)C8—C3—H3106 (2)
C26—O2—Ni1127.4 (3)N2—C8—C7117.1 (4)
N1—C1—C11125.2 (4)N2—C8—C3105.1 (3)
N1—C1—H1122 (3)C7—C8—C3111.3 (4)
C11—C1—H1112 (3)N2—C8—H8110 (2)
C16—C11—C12119.8 (4)C7—C8—H8110 (2)
C16—C11—C1121.2 (4)C3—C8—H8102 (3)
C12—C11—C1119.0 (4)C3—C4—C5108.3 (4)
C13—C12—C11121.7 (5)C3—C4—H41108 (3)
C13—C12—H12120 (3)C5—C4—H41113 (3)
C11—C12—H12118 (3)C3—C4—H42106 (4)
C12—C13—C14118.3 (4)C5—C4—H42116 (4)
C12—C13—H13120 (3)H41—C4—H42105 (5)
C14—C13—H13122 (3)C6—C5—C4112.4 (5)
C15—C14—C13121.9 (4)C6—C5—H51101 (5)
C15—C14—H14120 (3)C4—C5—H51101 (4)
C13—C14—H14118 (3)C6—C5—H52101 (3)
C14—C15—C16120.8 (4)C4—C5—H52110 (3)
C14—C15—H15122 (3)H51—C5—H52131 (5)
C16—C15—H15117 (3)C5—C6—C7112.6 (5)
O1—C16—C11124.2 (3)C5—C6—H6197 (3)
O1—C16—C15118.3 (4)C7—C6—H61110 (3)
C11—C16—C15117.5 (4)C5—C6—H62108 (4)
N2—C2—C21125.1 (4)C7—C6—H62111 (4)
N2—C2—H2122 (3)H61—C6—H62117 (5)
C21—C2—H2112 (3)C8—C7—C6109.4 (4)
C26—C21—C22119.5 (4)C8—C7—H71111 (3)
C26—C21—C2121.8 (4)C6—C7—H71113 (3)
C22—C21—C2118.5 (4)C8—C7—H72114 (3)
C23—C22—C21121.9 (5)C6—C7—H72107 (3)
C23—C22—H22117 (4)H71—C7—H72103 (5)
C21—C22—H22121 (4)Cl3—C10—Cl1113.6 (5)
C22—C23—C24118.3 (5)Cl3—C10—Cl2109.7 (4)
C22—C23—H23112 (3)Cl1—C10—Cl2110.4 (4)
C24—C23—H23130 (3)Cl3—C10—H10105 (5)
C25—C24—C23121.9 (5)Cl1—C10—H10113 (5)
C25—C24—H24124 (4)Cl2—C10—H10105 (5)
O1—Ni1—N1—C17.8 (4)Ni1—N2—C2—C210.9 (6)
O2—Ni1—N1—C168 (2)N2—C2—C21—C264.5 (6)
N2—Ni1—N1—C1169.7 (4)N2—C2—C21—C22178.5 (4)
O1—Ni1—N1—C3166.2 (3)C26—C21—C22—C231.2 (6)
O2—Ni1—N1—C3106 (2)C2—C21—C22—C23173.0 (4)
N2—Ni1—N1—C316.4 (3)C21—C22—C23—C240.6 (7)
O1—Ni1—N2—C268 (3)C22—C23—C24—C250.8 (8)
O2—Ni1—N2—C23.8 (3)C23—C24—C25—C261.6 (8)
N1—Ni1—N2—C2173.4 (3)Ni1—O2—C26—C25177.9 (3)
O1—Ni1—N2—C8107 (3)Ni1—O2—C26—C211.6 (6)
O2—Ni1—N2—C8171.6 (3)C24—C25—C26—O2178.4 (4)
N1—Ni1—N2—C811.2 (3)C24—C25—C26—C211.0 (7)
O2—Ni1—O1—C16169.0 (3)C22—C21—C26—O2179.7 (4)
N1—Ni1—O1—C1613.8 (3)C2—C21—C26—O25.8 (6)
N2—Ni1—O1—C16105 (3)C22—C21—C26—C250.3 (6)
O1—Ni1—O2—C26180.0 (4)C2—C21—C26—C25173.6 (4)
N1—Ni1—O2—C26120 (2)C1—N1—C3—C423.7 (6)
N2—Ni1—O2—C262.6 (4)Ni1—N1—C3—C4162.0 (4)
C3—N1—C1—C11174.2 (4)C1—N1—C3—C8147.2 (4)
Ni1—N1—C1—C110.8 (6)Ni1—N1—C3—C838.5 (4)
N1—C1—C11—C167.0 (6)C2—N2—C8—C725.7 (6)
N1—C1—C11—C12173.4 (4)Ni1—N2—C8—C7158.6 (3)
C16—C11—C12—C132.4 (6)C2—N2—C8—C3149.8 (4)
C1—C11—C12—C13178.0 (4)Ni1—N2—C8—C334.5 (4)
C11—C12—C13—C142.0 (7)N1—C3—C8—N244.7 (4)
C12—C13—C14—C150.5 (7)C4—C3—C8—N2172.0 (3)
C13—C14—C15—C160.6 (7)N1—C3—C8—C7172.4 (4)
Ni1—O1—C16—C1111.7 (5)C4—C3—C8—C760.2 (5)
Ni1—O1—C16—C15167.1 (3)N1—C3—C4—C5178.3 (4)
C12—C11—C16—O1180.0 (4)C8—C3—C4—C558.0 (6)
C1—C11—C16—O10.5 (6)C3—C4—C5—C655.8 (7)
C12—C11—C16—C151.2 (6)C4—C5—C6—C754.9 (8)
C1—C11—C16—C15179.3 (4)N2—C8—C7—C6177.0 (4)
C14—C15—C16—O1178.6 (4)C3—C8—C7—C656.0 (6)
C14—C15—C16—C110.3 (6)C5—C6—C7—C853.8 (7)
C8—N2—C2—C21174.2 (4)
Comparison of geometric parameters for similar Schiff base Ni complexes (Å, °) top
Title compound[Ni(-)chxn(sal)2][Ni(-)chxn(hapi)2]Ni[α,α'-Mesalhd)]
D10.044 (2)±0.08±0.0039±0.076
D20.002 (2)0.06-0.0290.018
A16.1 (2)8.9 (3)/10.3 (2)43.5 (1)49.9
A29.9 (2)4.0 (2)/7.3 (2)24.9 (2)21.3
A34.0 (2)4.9 (3)/4.7 (2)19.0 (2)28.7
A4-44.7 (4)-46.3 (6)/-46.1 (6)-39.0 (5)41.8(1.4)
Notes: D1 = maximum deviation from plane N2O2; D2 = deviation of Ni atom from least-squares plane N2O2; A1 = dihedral angle between the two chelating rings; A2 = angle between the N2O2 plane and the N1···O1 plane; A3 = angle between the N2O2 plane and the N2···O2 plane; A4 = N-C-C-N torsion angle.
 

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