Literature DB >> 21582091

{2,2'-[Cyclo-hexane-1,2-diylbis(nitrilo-methyl-idyne)]diphenolato}nickel(II).

Chunbao Tang1.   

Abstract

In the title mononuclear nickel(II) complex, [Ni(C(20)H(20)N(2)O(2))], the Ni atom is four-coordinated in a square-planar geometry by the four donor atoms of the Schiff base ligand. The dihedral angle between the two benzene rings is 9.4 (2)°. The cyclo-hexyl group adopts a C-form chair conformation.

Entities:  

Year:  2009        PMID： 21582091      PMCID： PMC2968678          DOI： 10.1107/S1600536809006084

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For nickel(II) complexes in bio-inorganic chemistry and coordination chemistry, see: Angulo et al. (2001 ▶); Dey et al. (2004 ▶); Edison et al. (2004 ▶); Ramadevi et al. (2005 ▶); Suh et al. (1996 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

[Ni(C20H20N2O2)] M = 379.09 Monoclinic, a = 7.6193 (8) Å b = 19.118 (2) Å c = 11.5459 (12) Å β = 90.907 (1)° V = 1681.6 (3) Å3 Z = 4 Mo Kα radiation μ = 1.17 mm−1 T = 298 K 0.30 × 0.30 × 0.28 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.721, T max = 0.735 9694 measured reflections 3650 independent reflections 3023 reflections with I > 2σ(I) R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.027 wR(F 2) = 0.069 S = 1.05 3650 reflections 226 parameters H-atom parameters constrained Δρmax = 0.29 e Å−3 Δρmin = −0.22 e Å−3 Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006084/bq2125sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006084/bq2125Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Ni(C20H20N2O2)]F(000) = 792
Mr = 379.09Dx = 1.497 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 7.6193 (8) ÅCell parameters from 3779 reflections
b = 19.118 (2) Åθ = 2.6–28.6°
c = 11.5459 (12) ŵ = 1.17 mm−1
β = 90.907 (1)°T = 298 K
V = 1681.6 (3) Å3Block, red
Z = 40.30 × 0.30 × 0.28 mm
Bruker SMART CCD area-detector diffractometer3650 independent reflections
Radiation source: fine-focus sealed tube3023 reflections with I > 2σ(I)
graphiteRint = 0.022
ω scansθmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→9
Tmin = 0.721, Tmax = 0.735k = −24→24
9694 measured reflectionsl = −14→9
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.027Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.069H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.033P)2 + 0.2023P] where P = (Fo2 + 2Fc2)/3
3650 reflections(Δ/σ)max = 0.001
226 parametersΔρmax = 0.28 e Å−3
0 restraintsΔρmin = −0.22 e Å−3
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.
xyzUiso*/Ueq
Ni10.80232 (3)0.468244 (10)0.481224 (17)0.03293 (8)
O10.86946 (19)0.37326 (6)0.49143 (10)0.0477 (3)
O20.89546 (18)0.48282 (6)0.63411 (11)0.0484 (3)
N10.6899 (2)0.45709 (7)0.33007 (12)0.0378 (3)
N20.7259 (2)0.56527 (7)0.46659 (12)0.0386 (3)
C10.8626 (2)0.32645 (9)0.40841 (15)0.0395 (4)
C20.9388 (3)0.26009 (9)0.42918 (17)0.0472 (5)
H20.98990.25080.50120.057*
C30.9392 (3)0.20924 (9)0.34579 (18)0.0500 (5)
H30.99030.16610.36250.060*
C40.8651 (3)0.22058 (10)0.23682 (18)0.0526 (5)
H40.86710.18590.18040.063*
C50.7887 (3)0.28423 (9)0.21422 (17)0.0488 (5)
H50.73830.29230.14150.059*
C60.7842 (2)0.33781 (9)0.29806 (15)0.0386 (4)
C70.6995 (2)0.40218 (9)0.26570 (15)0.0412 (4)
H70.64730.40440.19240.049*
C80.5917 (3)0.52030 (8)0.29253 (16)0.0401 (4)
H80.47670.51850.32920.048*
C90.5592 (3)0.52841 (9)0.16326 (16)0.0482 (5)
H9A0.48940.48950.13460.058*
H9B0.67030.52810.12330.058*
C100.4630 (3)0.59708 (10)0.13887 (18)0.0565 (5)
H10A0.44990.60320.05580.068*
H10B0.34640.59470.17120.068*
C110.5588 (3)0.65940 (10)0.18949 (17)0.0555 (5)
H11A0.49000.70130.17550.067*
H11B0.67030.66490.15120.067*
C120.5911 (3)0.65080 (9)0.31981 (16)0.0488 (5)
H12A0.65900.69010.34900.059*
H12B0.47970.65020.35940.059*
C130.6899 (2)0.58284 (9)0.34426 (15)0.0419 (4)
H130.80320.58600.30560.050*
C140.7157 (2)0.60977 (9)0.54952 (16)0.0423 (4)
H140.67330.65410.53150.051*
C150.7650 (2)0.59611 (9)0.66825 (15)0.0397 (4)
C160.7300 (3)0.64851 (10)0.75078 (17)0.0478 (5)
H160.67260.68900.72680.057*
C170.7777 (3)0.64176 (10)0.86443 (17)0.0551 (5)
H170.75120.67660.91750.066*
C180.8670 (3)0.58153 (11)0.89957 (17)0.0547 (5)
H180.90100.57640.97680.066*
C190.9054 (3)0.52957 (10)0.82153 (16)0.0478 (5)
H190.96630.49020.84690.057*
C200.8544 (2)0.53471 (8)0.70409 (15)0.0398 (4)
U11U22U33U12U13U23
Ni10.03599 (14)0.03109 (12)0.03155 (13)0.00174 (9)−0.00469 (9)−0.00265 (8)
O10.0670 (9)0.0363 (6)0.0396 (7)0.0052 (6)−0.0079 (6)−0.0018 (5)
O20.0549 (9)0.0475 (7)0.0424 (7)0.0133 (6)−0.0129 (6)−0.0091 (6)
N10.0390 (9)0.0359 (7)0.0382 (8)−0.0005 (6)−0.0033 (6)−0.0002 (6)
N20.0408 (9)0.0366 (7)0.0383 (8)0.0000 (6)−0.0041 (6)−0.0020 (6)
C10.0409 (10)0.0362 (9)0.0415 (10)−0.0038 (7)0.0029 (8)0.0004 (7)
C20.0541 (12)0.0384 (9)0.0491 (11)0.0025 (8)−0.0001 (9)0.0025 (8)
C30.0547 (13)0.0345 (9)0.0609 (13)0.0020 (8)0.0081 (10)0.0003 (8)
C40.0640 (14)0.0391 (10)0.0548 (13)−0.0022 (9)0.0059 (10)−0.0113 (9)
C50.0580 (13)0.0442 (10)0.0442 (11)−0.0040 (9)−0.0020 (9)−0.0057 (8)
C60.0406 (10)0.0365 (9)0.0388 (9)−0.0046 (7)0.0013 (8)−0.0021 (7)
C70.0441 (11)0.0425 (9)0.0369 (10)−0.0049 (8)−0.0055 (8)−0.0036 (8)
C80.0400 (10)0.0393 (9)0.0410 (10)0.0001 (7)−0.0040 (8)0.0013 (7)
C90.0525 (12)0.0489 (11)0.0429 (11)0.0013 (9)−0.0084 (9)−0.0008 (8)
C100.0652 (14)0.0527 (11)0.0511 (12)0.0051 (10)−0.0157 (10)0.0055 (9)
C110.0613 (14)0.0498 (11)0.0550 (12)0.0024 (10)−0.0072 (10)0.0114 (9)
C120.0562 (13)0.0391 (10)0.0507 (11)0.0022 (9)−0.0070 (9)0.0029 (8)
C130.0437 (11)0.0412 (9)0.0408 (10)−0.0031 (8)−0.0016 (8)0.0030 (7)
C140.0443 (11)0.0349 (9)0.0476 (11)−0.0004 (8)−0.0023 (8)−0.0030 (8)
C150.0389 (10)0.0396 (9)0.0406 (10)−0.0043 (8)0.0003 (8)−0.0051 (7)
C160.0510 (12)0.0420 (10)0.0506 (12)−0.0018 (9)0.0021 (9)−0.0090 (8)
C170.0660 (14)0.0536 (11)0.0458 (12)−0.0066 (10)0.0056 (10)−0.0159 (9)
C180.0616 (14)0.0647 (13)0.0377 (11)−0.0109 (10)−0.0017 (9)−0.0072 (9)
C190.0515 (12)0.0506 (11)0.0413 (11)−0.0033 (9)−0.0053 (9)−0.0010 (8)
C200.0376 (10)0.0426 (9)0.0391 (10)−0.0050 (8)−0.0010 (8)−0.0047 (8)
Ni1—O11.8897 (12)C9—C101.528 (2)
Ni1—O21.9125 (12)C9—H9A0.9700
Ni1—N11.9435 (15)C9—H9B0.9700
Ni1—N21.9507 (14)C10—C111.510 (3)
O1—C11.312 (2)C10—H10A0.9700
O2—C201.320 (2)C10—H10B0.9700
N1—C71.289 (2)C11—C121.530 (3)
N1—C81.483 (2)C11—H11A0.9700
N2—C141.284 (2)C11—H11B0.9700
N2—C131.473 (2)C12—C131.526 (2)
C1—C21.414 (2)C12—H12A0.9700
C1—C61.415 (2)C12—H12B0.9700
C2—C31.368 (2)C13—H130.9800
C2—H20.9300C14—C151.439 (2)
C3—C41.388 (3)C14—H140.9300
C3—H30.9300C15—C161.411 (2)
C4—C51.372 (3)C15—C201.416 (2)
C4—H40.9300C16—C171.362 (3)
C5—C61.410 (2)C16—H160.9300
C5—H50.9300C17—C181.394 (3)
C6—C71.437 (2)C17—H170.9300
C7—H70.9300C18—C191.376 (3)
C8—C91.517 (2)C18—H180.9300
C8—C131.527 (2)C19—C201.408 (3)
C8—H80.9800C19—H190.9300
O1—Ni1—O289.22 (5)H9A—C9—H9B108.2
O1—Ni1—N193.76 (5)C11—C10—C9112.26 (17)
O2—Ni1—N1175.27 (6)C11—C10—H10A109.2
O1—Ni1—N2177.83 (6)C9—C10—H10A109.2
O2—Ni1—N292.71 (5)C11—C10—H10B109.2
N1—Ni1—N284.25 (6)C9—C10—H10B109.2
C1—O1—Ni1127.04 (11)H10A—C10—H10B107.9
C20—O2—Ni1125.90 (11)C10—C11—C12111.42 (16)
C7—N1—C8121.87 (15)C10—C11—H11A109.3
C7—N1—Ni1125.39 (12)C12—C11—H11A109.3
C8—N1—Ni1112.73 (10)C10—C11—H11B109.3
C14—N2—C13123.45 (15)C12—C11—H11B109.3
C14—N2—Ni1125.94 (13)H11A—C11—H11B108.0
C13—N2—Ni1110.53 (10)C13—C12—C11110.17 (16)
O1—C1—C2118.46 (16)C13—C12—H12A109.6
O1—C1—C6124.38 (16)C11—C12—H12A109.6
C2—C1—C6117.16 (16)C13—C12—H12B109.6
C3—C2—C1121.58 (18)C11—C12—H12B109.6
C3—C2—H2119.2H12A—C12—H12B108.1
C1—C2—H2119.2N2—C13—C12117.09 (15)
C2—C3—C4121.41 (18)N2—C13—C8106.20 (13)
C2—C3—H3119.3C12—C13—C8110.91 (15)
C4—C3—H3119.3N2—C13—H13107.4
C5—C4—C3118.45 (18)C12—C13—H13107.4
C5—C4—H4120.8C8—C13—H13107.4
C3—C4—H4120.8N2—C14—C15124.88 (16)
C4—C5—C6121.89 (19)N2—C14—H14117.6
C4—C5—H5119.1C15—C14—H14117.6
C6—C5—H5119.1C16—C15—C20119.10 (16)
C5—C6—C1119.49 (16)C16—C15—C14117.73 (16)
C5—C6—C7117.35 (16)C20—C15—C14123.08 (15)
C1—C6—C7123.16 (15)C17—C16—C15122.23 (18)
N1—C7—C6125.24 (16)C17—C16—H16118.9
N1—C7—H7117.4C15—C16—H16118.9
C6—C7—H7117.4C16—C17—C18118.67 (18)
N1—C8—C9116.41 (14)C16—C17—H17120.7
N1—C8—C13106.37 (14)C18—C17—H17120.7
C9—C8—C13112.08 (15)C19—C18—C17120.90 (19)
N1—C8—H8107.2C19—C18—H18119.5
C9—C8—H8107.2C17—C18—H18119.5
C13—C8—H8107.2C18—C19—C20121.48 (18)
C8—C9—C10109.85 (15)C18—C19—H19119.3
C8—C9—H9A109.7C20—C19—H19119.3
C10—C9—H9A109.7O2—C20—C19118.21 (16)
C8—C9—H9B109.7O2—C20—C15124.17 (16)
C10—C9—H9B109.7C19—C20—C15117.61 (16)
Ni1—O11.8897 (12)
Ni1—O21.9125 (12)
Ni1—N11.9435 (15)
Ni1—N21.9507 (14)
O1—Ni1—O289.22 (5)
O1—Ni1—N193.76 (5)
O2—Ni1—N1175.27 (6)
O1—Ni1—N2177.83 (6)
O2—Ni1—N292.71 (5)
N1—Ni1—N284.25 (6)
  3 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Autoionization of homogeneous nickel(II) diphosphane hydrogenation catalysts. An NMR study and crystal structures of [Ni(o-MeO-dppe)I2] and [Ni(o-MeO-dppe)I2](PF6)2.

Authors:  I M Angulo; E Bouwman; M Lutz; W P Mul; A L Spek
Journal:  Inorg Chem       Date:  2001-04-23       Impact factor: 5.165

3.  Crystal structure and magnetic interactions in nickel(II) dibridged complexes formed by two azide groups or by both phenolate oxygen-azide, -thiocyanate, -carboxylate, or -cyanate groups.

Authors:  Subrata Kumar Dey; Nijhuma Mondal; M Salah El Fallah; Ramon Vicente; Albert Escuer; Xavier Solans; M Font-Bardía; T Matsushita; V Gramlich; Samiran Mitra
Journal:  Inorg Chem       Date:  2004-04-05       Impact factor: 5.165
  3 in total
  4 in total

1.  Bis(2-imino-methyl-5-methoxy-phenolato)nickel(II).

Authors:  Chunbao Tang
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-10-03

2.  Aqua{5,5'-dimethoxy-2,2-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato}nickel(II).

Authors:  Chunbao Tang
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-10-03

3.  {6,6'-Dimeth-oxy-2,2'-[cyclo-hexane-1,2-diylbis(nitrilo-methanylyl-idene)]diphenolato}copper(II) monohydrate.

Authors:  Chunmei Hu; Shunsheng Zhao; Xingqiang Lü; Rong Lu
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-11-10

4.  {2,2'-[Cyclo-hexane-1,2-diylbis(nitrilo-methanyl-ylidene)]diphenolato}copper(II).

Authors:  Shunsheng Zhao; Xingqiang Lü; Xiangrong Liu
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-08-25
  4 in total

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