Retracted: Bis[6-(cyclo­pentyl­imino­meth­yl)-2-meth­oxyphenolato]nickel(II)

The mol­ecule of the title mononuclear compound, [Ni(C₁₃H₁₆NO₂)₂], possesses crystallographic inversion symmetry. The Ni atom, lying on the inversion centre, is four-coordinated in a square-planar geometry by two Schiff base ligands.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.028
• wR factor = 0.075
• Data-to-parameter ratio = 17.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   O1      ..       8.44 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   N1      ..       8.35 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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: SHELXL97.

Bis[2-methoxy-6-(cyclopentyliminomethyl)phenolato]nickel(II)

Crystal data

[Ni(C13H16NO2)2]	Dx = 1.410 Mg m^−3
Mr = 495.25	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 4451 reflections
a = 12.062 (1) Å	θ = 2.3–27.8°
b = 10.811 (1) Å	µ = 0.87 mm^−1
c = 17.887 (2) Å	T = 298 K
V = 2332.5 (4) Å^3	Block, red
Z = 4	0.23 × 0.22 × 0.18 mm
F(000) = 1048

Data collection

Bruker SMART CCD area-detector diffractometer	2675 independent reflections
Radiation source: fine-focus sealed tube	2037 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
ω scans	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→14
Tmin = 0.825, Tmax = 0.860	k = −8→14
13173 measured reflections	l = −22→23

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.075	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0329P)^2 + 0.6139P] where P = (Fo^2 + 2Fc^2)/3
2675 reflections	(Δ/σ)max < 0.001
152 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Ni1	0.5000	1.0000	0.5000	0.03071 (9)
O1	0.51912 (10)	1.06076 (13)	0.40254 (7)	0.0516 (3)
O2	0.52117 (11)	1.21280 (13)	0.28885 (7)	0.0577 (4)
N1	0.62810 (11)	0.88123 (11)	0.48663 (7)	0.0346 (3)
C1	0.69875 (13)	0.98096 (14)	0.37351 (9)	0.0379 (4)
C2	0.60761 (13)	1.05903 (14)	0.36073 (8)	0.0371 (3)
C3	0.61227 (14)	1.13842 (15)	0.29728 (9)	0.0419 (4)
C4	0.70261 (16)	1.13772 (17)	0.25062 (10)	0.0517 (4)
H4	0.7038	1.1897	0.2092	0.062*
C5	0.79286 (16)	1.05977 (19)	0.26462 (11)	0.0558 (5)
H5	0.8539	1.0606	0.2329	0.067*
C6	0.79092 (15)	0.98296 (17)	0.32468 (10)	0.0494 (4)
H6	0.8509	0.9311	0.3338	0.059*
C7	0.50876 (18)	1.2772 (2)	0.21991 (13)	0.0724 (7)
H7A	0.5685	1.3351	0.2141	0.109*
H7B	0.4394	1.3209	0.2198	0.109*
H7C	0.5100	1.2192	0.1793	0.109*
C8	0.69986 (13)	0.89331 (14)	0.43407 (9)	0.0385 (4)
H8	0.7596	0.8390	0.4353	0.046*
C9	0.64305 (12)	0.78001 (13)	0.54143 (8)	0.0356 (3)
H9	0.6301	0.8151	0.5912	0.043*
C10	0.55838 (16)	0.67680 (17)	0.53016 (12)	0.0575 (5)
H10A	0.5488	0.6589	0.4774	0.069*
H10B	0.4872	0.6998	0.5512	0.069*
C11	0.60655 (17)	0.56522 (17)	0.57113 (13)	0.0650 (6)
H11A	0.5610	0.5441	0.6140	0.078*
H11B	0.6102	0.4942	0.5381	0.078*
C12	0.72244 (15)	0.60290 (15)	0.59623 (10)	0.0486 (4)
H12A	0.7222	0.6292	0.6481	0.058*
H12B	0.7742	0.5349	0.5905	0.058*
C13	0.75259 (14)	0.70978 (16)	0.54470 (10)	0.0441 (4)
H13A	0.7749	0.6806	0.4957	0.053*
H13B	0.8113	0.7603	0.5657	0.053*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.03133 (15)	0.03053 (15)	0.03026 (15)	0.00370 (11)	0.00270 (10)	0.00398 (10)
O1	0.0482 (7)	0.0625 (8)	0.0441 (7)	0.0187 (6)	0.0117 (5)	0.0185 (6)
O2	0.0607 (8)	0.0614 (9)	0.0510 (7)	0.0078 (6)	−0.0018 (6)	0.0220 (7)
N1	0.0362 (7)	0.0315 (6)	0.0362 (7)	0.0012 (5)	−0.0011 (5)	0.0001 (5)
C1	0.0386 (8)	0.0376 (9)	0.0376 (8)	−0.0024 (6)	0.0025 (7)	−0.0020 (6)
C2	0.0411 (9)	0.0375 (8)	0.0327 (7)	−0.0032 (7)	0.0023 (7)	−0.0017 (6)
C3	0.0484 (9)	0.0394 (9)	0.0378 (8)	−0.0042 (7)	−0.0027 (7)	0.0020 (7)
C4	0.0634 (12)	0.0513 (10)	0.0403 (9)	−0.0113 (9)	0.0065 (8)	0.0088 (8)
C5	0.0529 (11)	0.0645 (12)	0.0500 (11)	−0.0082 (10)	0.0166 (8)	0.0035 (9)
C6	0.0437 (10)	0.0547 (11)	0.0497 (10)	0.0011 (8)	0.0091 (8)	−0.0001 (8)
C7	0.0797 (15)	0.0747 (15)	0.0627 (13)	−0.0032 (11)	−0.0147 (11)	0.0327 (12)
C8	0.0367 (8)	0.0380 (8)	0.0408 (8)	0.0041 (6)	0.0001 (7)	−0.0021 (7)
C9	0.0376 (8)	0.0314 (8)	0.0378 (8)	0.0030 (6)	−0.0018 (7)	0.0016 (6)
C10	0.0527 (11)	0.0451 (10)	0.0747 (13)	−0.0097 (8)	−0.0191 (10)	0.0105 (9)
C11	0.0659 (13)	0.0391 (10)	0.0899 (15)	−0.0063 (9)	−0.0109 (12)	0.0103 (10)
C12	0.0576 (11)	0.0372 (9)	0.0509 (10)	0.0110 (8)	−0.0027 (8)	0.0020 (8)
C13	0.0430 (9)	0.0417 (9)	0.0474 (9)	0.0057 (7)	−0.0016 (8)	0.0020 (7)

Geometric parameters (Å, º)

Ni1—O1	1.8772 (12)	C7—H7A	0.960
Ni1—O1^i	1.8772 (12)	C7—H7B	0.960
Ni1—N1	2.0232 (13)	C7—H7C	0.960
Ni1—N1^i	2.0232 (13)	C8—H8	0.930
O1—C2	1.3035 (18)	C9—C13	1.525 (2)
O2—C3	1.370 (2)	C9—C10	1.526 (2)
O2—C7	1.424 (2)	C9—H9	0.980
N1—C8	1.2846 (19)	C10—C11	1.526 (3)
N1—C9	1.4801 (19)	C10—H10A	0.970
C1—C2	1.405 (2)	C10—H10B	0.970
C1—C6	1.414 (2)	C11—C12	1.524 (3)
C1—C8	1.439 (2)	C11—H11A	0.970
C2—C3	1.424 (2)	C11—H11B	0.970
C3—C4	1.373 (2)	C12—C13	1.522 (2)
C4—C5	1.399 (3)	C12—H12A	0.970
C4—H4	0.930	C12—H12B	0.970
C5—C6	1.358 (3)	C13—H13A	0.970
C5—H5	0.930	C13—H13B	0.970
C6—H6	0.930
O1—Ni1—O1^i	180	H7B—C7—H7C	109.5
O1—Ni1—N1	91.06 (5)	N1—C8—C1	127.70 (15)
O1^i—Ni1—N1	88.94 (5)	N1—C8—H8	116.1
O1—Ni1—N1^i	88.94 (5)	C1—C8—H8	116.1
O1^i—Ni1—N1^i	91.06 (5)	N1—C9—C13	119.94 (13)
N1—Ni1—N1^i	180	N1—C9—C10	111.82 (13)
C2—O1—Ni1	128.93 (10)	C13—C9—C10	102.76 (13)
C3—O2—C7	117.82 (15)	N1—C9—H9	107.2
C8—N1—C9	118.54 (13)	C13—C9—H9	107.2
C8—N1—Ni1	122.45 (11)	C10—C9—H9	107.2
C9—N1—Ni1	118.95 (9)	C9—C10—C11	105.06 (14)
C2—C1—C6	120.37 (15)	C9—C10—H10A	110.7
C2—C1—C8	121.69 (14)	C11—C10—H10A	110.7
C6—C1—C8	117.89 (15)	C9—C10—H10B	110.7
O1—C2—C1	123.79 (14)	C11—C10—H10B	110.7
O1—C2—C3	118.74 (14)	H10A—C10—H10B	108.8
C1—C2—C3	117.46 (14)	C12—C11—C10	106.23 (15)
O2—C3—C4	124.96 (15)	C12—C11—H11A	110.5
O2—C3—C2	114.20 (14)	C10—C11—H11A	110.5
C4—C3—C2	120.84 (16)	C12—C11—H11B	110.5
C3—C4—C5	120.81 (16)	C10—C11—H11B	110.5
C3—C4—H4	119.6	H11A—C11—H11B	108.7
C5—C4—H4	119.6	C13—C12—C11	104.10 (14)
C6—C5—C4	119.76 (17)	C13—C12—H12A	110.9
C6—C5—H5	120.1	C11—C12—H12A	110.9
C4—C5—H5	120.1	C13—C12—H12B	110.9
C5—C6—C1	120.77 (17)	C11—C12—H12B	110.9
C5—C6—H6	119.6	H12A—C12—H12B	109.0
C1—C6—H6	119.6	C12—C13—C9	101.20 (13)
O2—C7—H7A	109.5	C12—C13—H13A	111.5
O2—C7—H7B	109.5	C9—C13—H13A	111.5
H7A—C7—H7B	109.5	C12—C13—H13B	111.5
O2—C7—H7C	109.5	C9—C13—H13B	111.5
H7A—C7—H7C	109.5	H13A—C13—H13B	109.3

Symmetry code: (i) −x+1, −y+2, −z+1.