{4,4'-Dimeth-oxy-2,2'-[2,2-dimethyl-propane-1,3-diylbis(nitrilo-methyl-idyne)]diphenolato}nickel(II).

In the title complex, [Ni(C(21)H(24)N(2)O(4))], the Ni(II) ion has a slightly distorted square-planar geometry, coordinated by the two N and two O atoms of a new tetra-dentate Schiff base ligand. The dihedral angle between the planes of the two NiNC(3)O chelate rings is 14.37 (12)°.

Related literature

For the structures of free Schiff bases, see: Garnovskii et al. (1993 ▶). Nickel(II) complexes with N2O2 Schiff-base ligands derived from salicylaldehyde have long been used as homogenous catalysts (Gosden et al., 1981 ▶; Healy & Pletcher, 1978 ▶). For related structures, see: Habibi et al. (2007a ▶,b ▶). For Ni—O and Ni—N distances, see: Akhtar (1981 ▶); Shkolnikova et al. (1970 ▶).

Experimental

Crystal data

[Ni(C21H24N2O4)]

M = 427.13

Orthorhombic,

a = 15.6110 (7) Å

b = 9.1151 (5) Å

c = 26.8142 (12) Å

V = 3815.5 (3) Å3

Z = 8

Mo Kα radiation

μ = 1.05 mm−1

T = 193 K

0.30 × 0.20 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.744, T max = 0.818

35644 measured reflections

4362 independent reflections

3946 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.071

S = 1.05

4362 reflections

258 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.18 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809019965/bt2968sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019965/bt2968Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ni(C21H24N2O4)]	Dx = 1.487 Mg m−3
Mr = 427.13	Mo Kα radiation, λ = 0.71075 Å
Orthorhombic, Pbca	Cell parameters from 27241 reflections
a = 15.6110 (7) Å	θ = 3.0–27.5°
b = 9.1151 (5) Å	µ = 1.05 mm−1
c = 26.8142 (12) Å	T = 193 K
V = 3815.5 (3) Å3	Block, dark-green
Z = 8	0.30 × 0.20 × 0.20 mm
F(000) = 1792

Rigaku R-AXIS RAPID diffractometer	4362 independent reflections
Radiation source: fine-focus sealed tube	3946 reflections with I > 2σ(I)
graphite	Rint = 0.020
Detector resolution: 10.00 pixels mm-1	θmax = 27.5°, θmin = 3.0°
ω scans	h = −20→20
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −11→11
Tmin = 0.744, Tmax = 0.818	l = −34→32
35644 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.071	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0413P)2 + 1.3733P] where P = (Fo2 + 2Fc2)/3
4362 reflections	(Δ/σ)max = 0.001
258 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.18 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.

	x	y	z	Uiso*/Ueq
Ni1	0.951753 (10)	0.180679 (18)	0.014687 (6)	0.02025 (7)
O1	0.85263 (6)	0.10007 (11)	0.04139 (3)	0.0281 (2)
O2	0.91005 (6)	0.10714 (11)	−0.04479 (3)	0.0271 (2)
O3	0.75989 (7)	0.00704 (12)	0.23785 (4)	0.0353 (2)
O4	1.01038 (8)	0.20756 (14)	−0.23918 (4)	0.0398 (3)
N1	0.97892 (7)	0.27883 (12)	0.07416 (4)	0.0215 (2)
N2	1.05801 (7)	0.23220 (13)	−0.01347 (4)	0.0209 (2)
C1	0.83516 (8)	0.08183 (15)	0.08876 (5)	0.0234 (3)
C2	0.76375 (9)	−0.00620 (16)	0.10235 (5)	0.0287 (3)
H2	0.7304	−0.0512	0.0770	0.034*
C3	0.74193 (9)	−0.02755 (16)	0.15133 (5)	0.0304 (3)
H3	0.6940	−0.0874	0.1592	0.036*
C4	0.78912 (9)	0.03727 (15)	0.19010 (5)	0.0273 (3)
C5	0.85834 (8)	0.12301 (15)	0.17879 (5)	0.0252 (3)
H5	0.8908	0.1669	0.2048	0.030*
C6	0.88167 (8)	0.14645 (14)	0.12825 (5)	0.0227 (3)
C7	0.94728 (8)	0.25124 (15)	0.11773 (5)	0.0229 (3)
H7	0.9696	0.3053	0.1451	0.028*
C8	0.79861 (12)	0.0897 (2)	0.27678 (6)	0.0436 (4)
H8A	0.7692	0.0693	0.3083	0.052*
H8B	0.7942	0.1946	0.2691	0.052*
H8C	0.8591	0.0623	0.2797	0.052*
C9	1.03568 (8)	0.40646 (14)	0.06956 (5)	0.0231 (3)
H9A	1.0336	0.4635	0.1009	0.028*
H9B	1.0144	0.4704	0.0424	0.028*
C10	1.12843 (8)	0.36428 (15)	0.05867 (5)	0.0238 (3)
C11	0.93847 (8)	0.13593 (15)	−0.08973 (5)	0.0232 (3)
C12	0.88895 (9)	0.08927 (15)	−0.13120 (5)	0.0272 (3)
H12	0.8368	0.0382	−0.1255	0.033*
C13	0.91455 (9)	0.11618 (16)	−0.17925 (5)	0.0290 (3)
H13	0.8794	0.0852	−0.2062	0.035*
C14	0.99180 (10)	0.18878 (15)	−0.18915 (5)	0.0289 (3)
C15	1.04265 (9)	0.23295 (16)	−0.15007 (5)	0.0272 (3)
H15	1.0956	0.2807	−0.1565	0.033*
C16	1.01630 (9)	0.20742 (14)	−0.10023 (5)	0.0228 (3)
C17	1.07511 (8)	0.23987 (14)	−0.06053 (5)	0.0226 (2)
H17	1.1313	0.2695	−0.0697	0.027*
C18	1.08696 (13)	0.2857 (2)	−0.24969 (6)	0.0474 (4)
H18A	1.0940	0.2950	−0.2859	0.057*
H18B	1.1360	0.2325	−0.2357	0.057*
H18C	1.0838	0.3836	−0.2347	0.057*
C19	1.13172 (8)	0.23648 (15)	0.02101 (5)	0.0230 (3)
H19A	1.1851	0.2446	0.0012	0.028*
H19B	1.1341	0.1428	0.0396	0.028*
C20	1.17187 (10)	0.31209 (18)	0.10659 (6)	0.0349 (3)
H20A	1.2295	0.2761	0.0988	0.042*
H20B	1.1381	0.2328	0.1215	0.042*
H20C	1.1759	0.3940	0.1302	0.042*
C21	1.17386 (10)	0.49902 (17)	0.03763 (6)	0.0364 (3)
H21A	1.2348	0.4769	0.0329	0.044*
H21B	1.1678	0.5811	0.0610	0.044*
H21C	1.1482	0.5256	0.0055	0.044*

	U11	U22	U33	U12	U13	U23
Ni1	0.01948 (10)	0.02097 (10)	0.02030 (10)	−0.00186 (6)	0.00049 (6)	−0.00188 (6)
O1	0.0253 (5)	0.0358 (5)	0.0231 (4)	−0.0077 (4)	0.0010 (4)	−0.0026 (4)
O2	0.0279 (5)	0.0305 (5)	0.0229 (4)	−0.0065 (4)	0.0015 (4)	−0.0025 (4)
O3	0.0381 (6)	0.0421 (6)	0.0258 (5)	−0.0117 (5)	0.0024 (5)	0.0073 (4)
O4	0.0459 (7)	0.0524 (7)	0.0211 (5)	−0.0077 (5)	−0.0003 (5)	0.0034 (4)
N1	0.0194 (5)	0.0200 (5)	0.0250 (5)	−0.0007 (4)	0.0011 (4)	−0.0019 (4)
N2	0.0207 (5)	0.0189 (5)	0.0230 (5)	0.0012 (4)	−0.0007 (4)	−0.0017 (4)
C1	0.0212 (6)	0.0239 (6)	0.0253 (6)	0.0006 (5)	0.0014 (5)	−0.0005 (5)
C2	0.0258 (7)	0.0303 (7)	0.0302 (7)	−0.0059 (5)	−0.0019 (6)	−0.0016 (5)
C3	0.0267 (7)	0.0312 (7)	0.0332 (7)	−0.0076 (5)	0.0014 (6)	0.0037 (6)
C4	0.0290 (7)	0.0281 (7)	0.0248 (6)	−0.0009 (5)	0.0019 (5)	0.0047 (5)
C5	0.0245 (6)	0.0275 (7)	0.0236 (6)	−0.0004 (5)	−0.0014 (5)	0.0009 (5)
C6	0.0209 (6)	0.0223 (6)	0.0248 (6)	0.0005 (5)	0.0010 (5)	−0.0006 (5)
C7	0.0217 (6)	0.0235 (7)	0.0236 (6)	0.0005 (5)	−0.0012 (5)	−0.0031 (5)
C8	0.0474 (9)	0.0601 (11)	0.0234 (7)	−0.0133 (8)	−0.0003 (7)	0.0057 (7)
C9	0.0246 (6)	0.0191 (6)	0.0255 (6)	−0.0018 (5)	0.0024 (5)	−0.0028 (5)
C10	0.0213 (6)	0.0239 (6)	0.0262 (6)	−0.0031 (5)	0.0005 (5)	−0.0032 (5)
C11	0.0256 (6)	0.0198 (6)	0.0242 (6)	0.0024 (5)	0.0003 (5)	−0.0024 (5)
C12	0.0257 (6)	0.0267 (7)	0.0292 (7)	−0.0003 (5)	−0.0016 (5)	−0.0041 (5)
C13	0.0321 (7)	0.0295 (7)	0.0254 (6)	0.0030 (6)	−0.0053 (6)	−0.0042 (5)
C14	0.0356 (8)	0.0293 (7)	0.0219 (6)	0.0026 (6)	0.0003 (6)	0.0011 (5)
C15	0.0291 (7)	0.0263 (7)	0.0262 (7)	−0.0006 (5)	0.0019 (5)	0.0007 (5)
C16	0.0256 (6)	0.0200 (6)	0.0230 (6)	0.0016 (5)	−0.0004 (5)	−0.0018 (5)
C17	0.0226 (6)	0.0196 (6)	0.0257 (6)	−0.0004 (5)	0.0019 (5)	−0.0018 (5)
C18	0.0581 (11)	0.0578 (11)	0.0264 (7)	−0.0113 (9)	0.0073 (8)	0.0074 (7)
C19	0.0190 (6)	0.0244 (6)	0.0256 (6)	0.0011 (5)	−0.0022 (5)	−0.0024 (5)
C20	0.0314 (7)	0.0428 (9)	0.0304 (7)	0.0021 (6)	−0.0072 (6)	−0.0077 (6)
C21	0.0331 (8)	0.0281 (7)	0.0480 (9)	−0.0089 (6)	0.0117 (7)	−0.0044 (6)

Ni1—O2	1.8483 (9)	C9—C10	1.5264 (17)
Ni1—O1	1.8566 (9)	C9—H9A	0.9900
Ni1—N1	1.8770 (11)	C9—H9B	0.9900
Ni1—N2	1.8821 (11)	C10—C21	1.5263 (19)
O1—C1	1.3098 (16)	C10—C20	1.529 (2)
O2—C11	1.3107 (16)	C10—C19	1.5425 (18)
O3—C4	1.3869 (16)	C11—C16	1.4072 (18)
O3—C8	1.4222 (19)	C11—C12	1.4196 (19)
O4—C14	1.3833 (17)	C12—C13	1.3710 (19)
O4—C18	1.420 (2)	C12—H12	0.9500
N1—C7	1.2932 (17)	C13—C14	1.401 (2)
N1—C9	1.4676 (16)	C13—H13	0.9500
N2—C17	1.2917 (17)	C14—C15	1.375 (2)
N2—C19	1.4765 (16)	C15—C16	1.4174 (19)
C1—C6	1.4124 (18)	C15—H15	0.9500
C1—C2	1.4211 (18)	C16—C17	1.4368 (18)
C2—C3	1.371 (2)	C17—H17	0.9500
C2—H2	0.9500	C18—H18A	0.9800
C3—C4	1.404 (2)	C18—H18B	0.9800
C3—H3	0.9500	C18—H18C	0.9800
C4—C5	1.3678 (19)	C19—H19A	0.9900
C5—C6	1.4195 (18)	C19—H19B	0.9900
C5—H5	0.9500	C20—H20A	0.9800
C6—C7	1.4286 (18)	C20—H20B	0.9800
C7—H7	0.9500	C20—H20C	0.9800
C8—H8A	0.9800	C21—H21A	0.9800
C8—H8B	0.9800	C21—H21B	0.9800
C8—H8C	0.9800	C21—H21C	0.9800
O2—Ni1—O1	84.02 (4)	C21—C10—C20	110.79 (12)
O2—Ni1—N1	170.21 (5)	C9—C10—C20	109.78 (11)
O1—Ni1—N1	92.82 (4)	C21—C10—C19	110.51 (11)
O2—Ni1—N2	93.14 (4)	C9—C10—C19	110.31 (10)
O1—Ni1—N2	171.13 (5)	C20—C10—C19	107.48 (11)
N1—Ni1—N2	91.30 (5)	O2—C11—C16	124.67 (12)
C1—O1—Ni1	126.72 (8)	O2—C11—C12	118.43 (12)
C11—O2—Ni1	126.98 (9)	C16—C11—C12	116.88 (12)
C4—O3—C8	115.62 (11)	C13—C12—C11	121.59 (13)
C14—O4—C18	115.53 (12)	C13—C12—H12	119.2
C7—N1—C9	117.43 (11)	C11—C12—H12	119.2
C7—N1—Ni1	126.06 (9)	C12—C13—C14	120.89 (13)
C9—N1—Ni1	116.29 (8)	C12—C13—H13	119.6
C17—N2—C19	116.69 (11)	C14—C13—H13	119.6
C17—N2—Ni1	125.98 (9)	C15—C14—O4	125.58 (14)
C19—N2—Ni1	116.25 (8)	C15—C14—C13	119.40 (13)
O1—C1—C6	124.53 (12)	O4—C14—C13	115.01 (13)
O1—C1—C2	118.93 (12)	C14—C15—C16	120.19 (13)
C6—C1—C2	116.53 (12)	C14—C15—H15	119.9
C3—C2—C1	121.38 (13)	C16—C15—H15	119.9
C3—C2—H2	119.3	C11—C16—C15	121.02 (12)
C1—C2—H2	119.3	C11—C16—C17	119.92 (12)
C2—C3—C4	121.28 (13)	C15—C16—C17	118.64 (12)
C2—C3—H3	119.4	N2—C17—C16	125.50 (12)
C4—C3—H3	119.4	N2—C17—H17	117.2
C5—C4—O3	125.32 (13)	C16—C17—H17	117.2
C5—C4—C3	119.38 (13)	O4—C18—H18A	109.5
O3—C4—C3	115.30 (12)	O4—C18—H18B	109.5
C4—C5—C6	120.03 (12)	H18A—C18—H18B	109.5
C4—C5—H5	120.0	O4—C18—H18C	109.5
C6—C5—H5	120.0	H18A—C18—H18C	109.5
C1—C6—C5	121.40 (12)	H18B—C18—H18C	109.5
C1—C6—C7	119.97 (12)	N2—C19—C10	113.82 (11)
C5—C6—C7	118.23 (12)	N2—C19—H19A	108.8
N1—C7—C6	125.60 (12)	C10—C19—H19A	108.8
N1—C7—H7	117.2	N2—C19—H19B	108.8
C6—C7—H7	117.2	C10—C19—H19B	108.8
O3—C8—H8A	109.5	H19A—C19—H19B	107.7
O3—C8—H8B	109.5	C10—C20—H20A	109.5
H8A—C8—H8B	109.5	C10—C20—H20B	109.5
O3—C8—H8C	109.5	H20A—C20—H20B	109.5
H8A—C8—H8C	109.5	C10—C20—H20C	109.5
H8B—C8—H8C	109.5	H20A—C20—H20C	109.5
N1—C9—C10	112.90 (10)	H20B—C20—H20C	109.5
N1—C9—H9A	109.0	C10—C21—H21A	109.5
C10—C9—H9A	109.0	C10—C21—H21B	109.5
N1—C9—H9B	109.0	H21A—C21—H21B	109.5
C10—C9—H9B	109.0	C10—C21—H21C	109.5
H9A—C9—H9B	107.8	H21A—C21—H21C	109.5
C21—C10—C9	107.99 (11)	H21B—C21—H21C	109.5
O2—Ni1—O1—C1	167.96 (12)	C9—N1—C7—C6	170.27 (12)
N1—Ni1—O1—C1	−21.33 (12)	Ni1—N1—C7—C6	−4.06 (19)
N2—Ni1—O1—C1	96.3 (3)	C1—C6—C7—N1	−11.4 (2)
O1—Ni1—O2—C11	168.52 (11)	C5—C6—C7—N1	175.86 (13)
N1—Ni1—O2—C11	97.0 (3)	C7—N1—C9—C10	112.05 (13)
N2—Ni1—O2—C11	−19.91 (11)	Ni1—N1—C9—C10	−73.06 (12)
O2—Ni1—N1—C7	87.7 (3)	N1—C9—C10—C21	161.18 (11)
O1—Ni1—N1—C7	16.86 (11)	N1—C9—C10—C20	−77.94 (14)
N2—Ni1—N1—C7	−155.28 (11)	N1—C9—C10—C19	40.32 (15)
O2—Ni1—N1—C9	−86.7 (3)	Ni1—O2—C11—C16	12.44 (19)
O1—Ni1—N1—C9	−157.53 (9)	Ni1—O2—C11—C12	−169.17 (9)
N2—Ni1—N1—C9	30.33 (9)	O2—C11—C12—C13	179.71 (13)
O2—Ni1—N2—C17	14.38 (12)	C16—C11—C12—C13	−1.8 (2)
O1—Ni1—N2—C17	85.4 (3)	C11—C12—C13—C14	1.2 (2)
N1—Ni1—N2—C17	−156.90 (12)	C18—O4—C14—C15	−3.2 (2)
O2—Ni1—N2—C19	−153.30 (9)	C18—O4—C14—C13	177.78 (14)
O1—Ni1—N2—C19	−82.3 (3)	C12—C13—C14—C15	0.3 (2)
N1—Ni1—N2—C19	35.43 (9)	C12—C13—C14—O4	179.37 (13)
Ni1—O1—C1—C6	13.03 (19)	O4—C14—C15—C16	179.91 (13)
Ni1—O1—C1—C2	−168.29 (10)	C13—C14—C15—C16	−1.1 (2)
O1—C1—C2—C3	−179.21 (13)	O2—C11—C16—C15	179.35 (13)
C6—C1—C2—C3	−0.4 (2)	C12—C11—C16—C15	0.93 (19)
C1—C2—C3—C4	0.3 (2)	O2—C11—C16—C17	6.8 (2)
C8—O3—C4—C5	9.4 (2)	C12—C11—C16—C17	−171.57 (12)
C8—O3—C4—C3	−170.61 (14)	C14—C15—C16—C11	0.5 (2)
C2—C3—C4—C5	−0.2 (2)	C14—C15—C16—C17	173.07 (13)
C2—C3—C4—O3	179.77 (14)	C19—N2—C17—C16	166.28 (12)
O3—C4—C5—C6	−179.65 (13)	Ni1—N2—C17—C16	−1.35 (19)
C3—C4—C5—C6	0.3 (2)	C11—C16—C17—N2	−12.5 (2)
O1—C1—C6—C5	179.26 (13)	C15—C16—C17—N2	174.77 (13)
C2—C1—C6—C5	0.56 (19)	C17—N2—C19—C10	121.25 (13)
O1—C1—C6—C7	6.7 (2)	Ni1—N2—C19—C10	−69.89 (13)
C2—C1—C6—C7	−171.96 (12)	C21—C10—C19—N2	−90.70 (14)
C4—C5—C6—C1	−0.5 (2)	C9—C10—C19—N2	28.64 (15)
C4—C5—C6—C7	172.12 (12)	C20—C10—C19—N2	148.30 (11)