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The title compound, [Ni(C19H20N2O2)], is mononuclear. The NiII atom is four-coordinated in a square-planar configuration by two N atoms and two O atoms of the Schiff base ligand. The mol­ecule possesses crystallographic mirror symmetry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805023470/ci6619sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805023470/ci6619Isup2.hkl
Contains datablock I

CCDC reference: 282297

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.035
  • wR factor = 0.087
  • Data-to-parameter ratio = 17.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT128_ALERT_4_C Non-standard setting of Space group Cmc21 .... A21am
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.49 From the CIF: _reflns_number_total 1960 Count of symmetry unique reflns 1078 Completeness (_total/calc) 181.82% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 882 Fraction of Friedel pairs measured 0.818 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

{6,6'-Dimethyl-2,2'-[propane-1,3- diylbis(nitrilomethylidyne)]diphenolato}nickel(II) top
Crystal data top
[Ni(C19H20N2O2)]F(000) = 768
Mr = 367.08Dx = 1.445 Mg m3
Orthorhombic, A21amMo Kα radiation, λ = 0.71073 Å
Hall symbol: A -2 2aCell parameters from 3072 reflections
a = 7.529 (2) Åθ = 3.4–23.9°
b = 10.399 (2) ŵ = 1.16 mm1
c = 21.555 (3) ÅT = 298 K
V = 1687.6 (6) Å3Plate, green
Z = 40.28 × 0.16 × 0.07 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1960 independent reflections
Radiation source: fine-focus sealed tube1821 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
ω scansθmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.737, Tmax = 0.923k = 1313
9442 measured reflectionsl = 2727
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.087 w = 1/[σ2(Fo2) + (0.0418P)2 + 0.6633P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
1960 reflectionsΔρmax = 0.32 e Å3
113 parametersΔρmin = 0.27 e Å3
1 restraintAbsolute structure: Flack (1983), 884 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.02 (2)
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
Ni10.02552 (6)0.45279 (4)0.50000.04266 (14)
O10.0117 (2)0.32166 (17)0.55633 (10)0.0516 (6)
N10.0720 (3)0.5708 (2)0.56462 (13)0.0531 (7)
C10.0733 (3)0.3056 (3)0.60830 (13)0.0468 (6)
C20.0820 (4)0.1810 (3)0.63460 (15)0.0579 (8)
C30.1782 (6)0.1635 (4)0.68811 (16)0.0738 (10)
H30.18380.08150.70520.089*
C40.2674 (7)0.2629 (4)0.71772 (16)0.0797 (11)
H40.33580.24720.75280.096*
C50.2528 (5)0.3829 (4)0.69447 (16)0.0712 (10)
H50.30620.45080.71540.085*
C60.1593 (4)0.4079 (3)0.63959 (14)0.0525 (7)
C70.0075 (6)0.0721 (3)0.6010 (2)0.0790 (13)
H7A0.02650.00810.61960.118*
H7B0.02780.07270.55820.118*
H7C0.13400.08210.60370.118*
C80.1381 (4)0.5359 (3)0.61724 (16)0.0565 (8)
H80.17600.60140.64340.068*
C90.0447 (7)0.7111 (3)0.55775 (17)0.0733 (10)
H9A0.15950.75350.55790.088*
H9B0.02160.74240.59330.088*
C100.0521 (7)0.7473 (5)0.50000.0764 (16)
H10A0.07190.83950.50000.092*
H10B0.16730.70550.50000.092*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0337 (2)0.02763 (19)0.0666 (3)0.0021 (2)0.0000.000
O10.0449 (15)0.0396 (10)0.0704 (13)0.0076 (8)0.0060 (9)0.0043 (8)
N10.0483 (18)0.0303 (11)0.0807 (17)0.0023 (8)0.0095 (12)0.0092 (10)
C10.0389 (15)0.0464 (14)0.0550 (15)0.0018 (10)0.0094 (10)0.0039 (12)
C20.0567 (18)0.0545 (17)0.0625 (17)0.0039 (12)0.0099 (13)0.0074 (14)
C30.082 (3)0.080 (2)0.0590 (19)0.0112 (19)0.0055 (18)0.0161 (17)
C40.086 (3)0.102 (3)0.0508 (18)0.006 (2)0.0022 (17)0.008 (2)
C50.069 (2)0.093 (3)0.0513 (18)0.010 (2)0.0058 (16)0.0173 (18)
C60.0495 (15)0.0542 (17)0.0538 (15)0.0014 (13)0.0113 (12)0.0103 (13)
C70.087 (4)0.0422 (15)0.108 (3)0.0046 (18)0.014 (2)0.0185 (16)
C80.0511 (18)0.0493 (17)0.0692 (19)0.0060 (13)0.0094 (15)0.0199 (14)
C90.070 (2)0.0332 (13)0.117 (3)0.0022 (18)0.002 (2)0.0102 (14)
C100.044 (2)0.042 (2)0.143 (5)0.0014 (19)0.0000.000
Geometric parameters (Å, º) top
Ni1—O1i1.847 (2)C4—H40.93
Ni1—O11.847 (2)C5—C61.401 (5)
Ni1—N11.889 (2)C5—H50.93
Ni1—N1i1.889 (2)C6—C81.424 (4)
O1—C11.301 (3)C7—H7A0.96
N1—C81.291 (4)C7—H7B0.96
N1—C91.481 (4)C7—H7C0.96
C1—C21.416 (4)C8—H80.93
C1—C61.417 (4)C9—C101.491 (5)
C2—C31.374 (5)C9—H9A0.97
C2—C71.504 (5)C9—H9B0.97
C3—C41.389 (6)C10—C9i1.491 (5)
C3—H30.93C10—H10A0.97
C4—C51.349 (6)C10—H10B0.97
O1i—Ni1—O182.18 (12)C5—C6—C1119.5 (3)
O1i—Ni1—N1172.88 (10)C5—C6—C8121.1 (3)
O1—Ni1—N191.31 (10)C1—C6—C8119.3 (3)
O1i—Ni1—N1i91.31 (10)C2—C7—H7A109.5
O1—Ni1—N1i172.88 (10)C2—C7—H7B109.5
N1—Ni1—N1i95.03 (16)H7A—C7—H7B109.5
C1—O1—Ni1125.88 (18)C2—C7—H7C109.5
C8—N1—C9114.7 (3)H7A—C7—H7C109.5
C8—N1—Ni1122.5 (2)H7B—C7—H7C109.5
C9—N1—Ni1122.7 (2)N1—C8—C6127.1 (3)
O1—C1—C2119.0 (3)N1—C8—H8116.4
O1—C1—C6122.6 (3)C6—C8—H8116.4
C2—C1—C6118.4 (3)N1—C9—C10113.6 (3)
C3—C2—C1118.8 (3)N1—C9—H9A108.9
C3—C2—C7122.7 (3)C10—C9—H9A108.9
C1—C2—C7118.4 (3)N1—C9—H9B108.9
C2—C3—C4122.8 (4)C10—C9—H9B108.9
C2—C3—H3118.6H9A—C9—H9B107.7
C4—C3—H3118.6C9—C10—C9i113.2 (5)
C5—C4—C3118.6 (4)C9—C10—H10A108.9
C5—C4—H4120.7C9i—C10—H10A108.9
C3—C4—H4120.7C9—C10—H10B108.9
C4—C5—C6121.8 (4)C9i—C10—H10B108.9
C4—C5—H5119.1H10A—C10—H10B107.7
C6—C5—H5119.1
O1i—Ni1—O1—C1141.21 (18)C3—C4—C5—C63.9 (6)
N1—Ni1—O1—C135.9 (2)C4—C5—C6—C11.8 (5)
O1—Ni1—N1—C828.8 (3)C4—C5—C6—C8177.0 (4)
N1i—Ni1—N1—C8147.9 (2)O1—C1—C6—C5178.1 (3)
O1—Ni1—N1—C9154.6 (3)C2—C1—C6—C51.3 (4)
N1i—Ni1—N1—C928.7 (3)O1—C1—C6—C86.5 (4)
Ni1—O1—C1—C2156.1 (2)C2—C1—C6—C8174.0 (3)
Ni1—O1—C1—C623.4 (3)C9—N1—C8—C6172.1 (3)
O1—C1—C2—C3177.3 (3)Ni1—N1—C8—C611.0 (5)
C6—C1—C2—C32.2 (4)C5—C6—C8—N1172.2 (3)
O1—C1—C2—C70.2 (4)C1—C6—C8—N112.6 (5)
C6—C1—C2—C7179.3 (3)C8—N1—C9—C10172.8 (3)
C1—C2—C3—C40.1 (5)Ni1—N1—C9—C1010.3 (5)
C7—C2—C3—C4177.1 (4)N1—C9—C10—C9i62.4 (6)
C2—C3—C4—C52.9 (6)
Symmetry code: (i) x, y, z+1.
 

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