{3,3',5,5'-Tetra-meth-oxy-2,2'-[ethane-1,2-diylbis(nitrilo-methyl-idyne)]diphenolato}nickel(II).

The title square-planar nickel complex, [Ni(C(20)H(22)N(2)O(6))], has Ni-N and Ni-O bond lengths of 1.8448 (14)/1.8478 (14) and 1.8536 (12)/1.8520 (12) Å. There is a slight twist in the two benzene rings at each end of the complex [dihedral angle = 11.11 (5)°]. All the atoms of the meth-oxy substitutents are in the plane of the ring to which they are attached except for one which deviates slightly [0.365 (3) Å]. In the crystal, weak C-H⋯O inter-molecular inter-actions connect the mol-ecules.

Related literature

For nickel–salen complexes with aromatic substituents, see: Bal & Ülküseven (2004 ▶). For their activation of O2, see: Soto-Garrodo & Salas-Reyes (2000 ▶); For their catalytic activity: Silva et al. (2002 ▶); Santos et al. (2000 ▶); Yoon & Burrows (1988 ▶). For the mesogenic properties of substituted complexes, see: Blake et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

[Ni(C20H22N2O6)]

M = 445.11

Monoclinic,

a = 7.41599 (12) Å

b = 15.6945 (2) Å

c = 15.7203 (2) Å

β = 91.9153 (13)°

V = 1828.67 (5) Å3

Z = 4

Cu Kα radiation

μ = 1.91 mm−1

T = 110 K

0.53 × 0.15 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 ▶) T min = 0.602, T max = 1.000

6746 measured reflections

3603 independent reflections

3370 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.098

S = 1.04

3603 reflections

266 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.47 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 I, global. DOI: 10.1107/S1600536810016041/bt5260sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016041/bt5260Isup2.hkl

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

[Ni(C20H22N2O6)]	F(000) = 928
Mr = 445.11	Dx = 1.617 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 5663 reflections
a = 7.41599 (12) Å	θ = 5.6–74.0°
b = 15.6945 (2) Å	µ = 1.91 mm−1
c = 15.7203 (2) Å	T = 110 K
β = 91.9153 (13)°	Needle, red
V = 1828.67 (5) Å3	0.53 × 0.15 × 0.12 mm
Z = 4

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	3603 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3370 reflections with I > 2σ(I)
graphite	Rint = 0.022
Detector resolution: 10.5081 pixels mm-1	θmax = 74.2°, θmin = 5.6°
ω scans	h = −9→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	k = −11→19
Tmin = 0.602, Tmax = 1.000	l = −18→19
6746 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0641P)2 + 1.0294P] where P = (Fo2 + 2Fc2)/3
3603 reflections	(Δ/σ)max < 0.001
266 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.47 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Ni	0.25525 (4)	0.522587 (16)	0.436449 (16)	0.01249 (11)
O1	0.25637 (17)	0.49637 (8)	0.32150 (7)	0.0166 (2)
O2	0.25493 (17)	0.63580 (7)	0.40321 (7)	0.0168 (2)
O3	0.36236 (18)	0.33461 (8)	0.07279 (8)	0.0209 (3)
O4	0.45100 (16)	0.20821 (7)	0.34353 (7)	0.0183 (3)
O5	0.10218 (18)	0.76296 (8)	0.66590 (7)	0.0192 (3)
O6	0.13141 (19)	0.93215 (8)	0.41651 (8)	0.0230 (3)
N1	0.26710 (19)	0.41000 (9)	0.46989 (8)	0.0143 (3)
N2	0.24084 (18)	0.54755 (10)	0.55089 (9)	0.0145 (3)
C1	0.3028 (2)	0.42368 (10)	0.28756 (10)	0.0142 (3)
C2	0.3067 (2)	0.41965 (10)	0.19756 (10)	0.0158 (3)
H2A	0.2743	0.4682	0.1643	0.019*
C3	0.3576 (2)	0.34513 (11)	0.15833 (10)	0.0163 (3)
C4	0.4124 (2)	0.27279 (11)	0.20515 (11)	0.0171 (3)
H4A	0.4539	0.2233	0.1771	0.020*
C5	0.4047 (2)	0.27513 (10)	0.29228 (11)	0.0150 (3)
C6	0.3462 (2)	0.34938 (10)	0.33579 (11)	0.0152 (3)
C7	0.3154 (2)	0.34535 (10)	0.42475 (11)	0.0145 (3)
H7A	0.3313	0.2920	0.4526	0.017*
C8	0.2141 (2)	0.39623 (11)	0.55814 (10)	0.0164 (3)
H8A	0.2732	0.3445	0.5820	0.020*
H8B	0.0818	0.3891	0.5605	0.020*
C9	0.2745 (2)	0.47426 (10)	0.60768 (11)	0.0171 (3)
H9A	0.2051	0.4801	0.6601	0.020*
H9B	0.4044	0.4702	0.6239	0.020*
C10	0.2071 (2)	0.62123 (11)	0.58443 (10)	0.0155 (3)
H10A	0.1973	0.6239	0.6445	0.019*
C11	0.1837 (2)	0.69804 (11)	0.53782 (10)	0.0155 (3)
C12	0.1328 (2)	0.77404 (11)	0.58121 (10)	0.0165 (3)
C13	0.1162 (2)	0.85044 (11)	0.53987 (11)	0.0188 (3)
H13A	0.0831	0.9005	0.5695	0.023*
C14	0.1498 (2)	0.85285 (11)	0.45184 (11)	0.0171 (3)
C15	0.1950 (2)	0.78148 (11)	0.40677 (10)	0.0165 (3)
H15A	0.2138	0.7853	0.3474	0.020*
C16	0.2134 (2)	0.70230 (10)	0.44895 (10)	0.0144 (3)
C17	0.3271 (3)	0.40816 (12)	0.02106 (11)	0.0264 (4)
H17A	0.3333	0.3925	−0.0391	0.040*
H17B	0.4174	0.4521	0.0347	0.040*
H17C	0.2065	0.4302	0.0322	0.040*
C18	0.5069 (3)	0.13184 (11)	0.30218 (12)	0.0213 (4)
H18A	0.5485	0.0903	0.3451	0.032*
H18B	0.6056	0.1450	0.2643	0.032*
H18C	0.4050	0.1080	0.2688	0.032*
C19	0.0109 (2)	0.83006 (11)	0.70858 (11)	0.0203 (4)
H19A	−0.0207	0.8109	0.7655	0.030*
H19B	−0.0992	0.8453	0.6759	0.030*
H19C	0.0901	0.8799	0.7136	0.030*
C20	0.1620 (3)	0.93901 (11)	0.32755 (12)	0.0232 (4)
H20A	0.1452	0.9983	0.3094	0.035*
H20B	0.0763	0.9025	0.2958	0.035*
H20C	0.2855	0.9209	0.3164	0.035*

	U11	U22	U33	U12	U13	U23
Ni	0.01826 (18)	0.00876 (17)	0.01067 (17)	0.00064 (10)	0.00377 (11)	−0.00065 (9)
O1	0.0266 (6)	0.0109 (5)	0.0127 (5)	0.0024 (5)	0.0038 (4)	−0.0009 (4)
O2	0.0253 (6)	0.0111 (5)	0.0144 (6)	0.0006 (5)	0.0071 (4)	−0.0013 (4)
O3	0.0311 (7)	0.0181 (6)	0.0139 (6)	0.0004 (5)	0.0046 (5)	−0.0034 (5)
O4	0.0253 (6)	0.0112 (5)	0.0185 (6)	0.0045 (5)	0.0019 (5)	−0.0026 (4)
O5	0.0298 (7)	0.0148 (6)	0.0135 (6)	0.0034 (5)	0.0054 (5)	−0.0033 (4)
O6	0.0381 (8)	0.0110 (6)	0.0205 (6)	0.0021 (5)	0.0089 (5)	0.0003 (5)
N1	0.0170 (7)	0.0130 (6)	0.0130 (6)	0.0002 (5)	0.0033 (5)	0.0006 (5)
N2	0.0174 (7)	0.0133 (7)	0.0129 (6)	0.0001 (5)	0.0024 (5)	0.0007 (5)
C1	0.0143 (7)	0.0117 (7)	0.0167 (8)	−0.0022 (6)	0.0027 (6)	−0.0022 (6)
C2	0.0188 (8)	0.0128 (8)	0.0158 (8)	−0.0016 (6)	0.0029 (6)	−0.0002 (6)
C3	0.0162 (8)	0.0180 (8)	0.0149 (8)	−0.0035 (6)	0.0045 (6)	−0.0033 (6)
C4	0.0178 (8)	0.0137 (8)	0.0200 (8)	−0.0006 (6)	0.0042 (6)	−0.0061 (6)
C5	0.0138 (7)	0.0118 (7)	0.0195 (8)	−0.0010 (6)	0.0020 (6)	−0.0022 (6)
C6	0.0156 (7)	0.0127 (8)	0.0175 (8)	−0.0012 (6)	0.0023 (6)	−0.0025 (6)
C7	0.0154 (8)	0.0103 (7)	0.0178 (8)	0.0005 (6)	0.0012 (6)	−0.0004 (6)
C8	0.0229 (8)	0.0131 (8)	0.0134 (8)	0.0023 (6)	0.0046 (6)	0.0025 (6)
C9	0.0229 (9)	0.0161 (8)	0.0122 (7)	0.0024 (6)	0.0023 (6)	0.0011 (6)
C10	0.0176 (8)	0.0164 (8)	0.0128 (7)	−0.0002 (6)	0.0031 (6)	−0.0025 (6)
C11	0.0173 (8)	0.0127 (8)	0.0166 (8)	−0.0009 (6)	0.0022 (6)	−0.0030 (6)
C12	0.0192 (8)	0.0159 (8)	0.0145 (7)	−0.0010 (6)	0.0028 (6)	−0.0039 (6)
C13	0.0244 (9)	0.0127 (8)	0.0196 (8)	0.0001 (6)	0.0044 (6)	−0.0051 (6)
C14	0.0202 (8)	0.0109 (7)	0.0204 (8)	−0.0006 (6)	0.0027 (6)	0.0006 (6)
C15	0.0213 (8)	0.0131 (8)	0.0154 (7)	−0.0019 (6)	0.0050 (6)	−0.0012 (6)
C16	0.0148 (7)	0.0118 (7)	0.0169 (8)	−0.0026 (6)	0.0037 (6)	−0.0023 (6)
C17	0.0445 (12)	0.0206 (9)	0.0144 (8)	−0.0075 (8)	0.0067 (7)	0.0003 (7)
C18	0.0266 (9)	0.0127 (8)	0.0249 (9)	0.0053 (7)	0.0051 (7)	−0.0042 (6)
C19	0.0239 (9)	0.0187 (8)	0.0186 (8)	0.0024 (7)	0.0061 (6)	−0.0051 (6)
C20	0.0318 (10)	0.0153 (8)	0.0231 (9)	0.0041 (7)	0.0105 (7)	0.0053 (7)

Ni—N1	1.8448 (14)	C8—C9	1.511 (2)
Ni—N2	1.8478 (14)	C8—H8A	0.9900
Ni—O2	1.8520 (12)	C8—H8B	0.9900
Ni—O1	1.8536 (12)	C9—H9A	0.9900
O1—C1	1.310 (2)	C9—H9B	0.9900
O2—C16	1.310 (2)	C10—C11	1.418 (2)
O3—C3	1.356 (2)	C10—H10A	0.9500
O3—C17	1.431 (2)	C11—C16	1.423 (2)
O4—C5	1.361 (2)	C11—C12	1.431 (2)
O4—C18	1.4316 (19)	C12—C13	1.368 (2)
O5—C12	1.369 (2)	C13—C14	1.415 (2)
O5—C19	1.4311 (19)	C13—H13A	0.9500
O6—C14	1.368 (2)	C14—C15	1.373 (2)
O6—C20	1.428 (2)	C15—C16	1.413 (2)
N1—C7	1.295 (2)	C15—H15A	0.9500
N1—C8	1.4705 (19)	C17—H17A	0.9800
N2—C10	1.299 (2)	C17—H17B	0.9800
N2—C9	1.472 (2)	C17—H17C	0.9800
C1—C2	1.418 (2)	C18—H18A	0.9800
C1—C6	1.422 (2)	C18—H18B	0.9800
C2—C3	1.381 (2)	C18—H18C	0.9800
C2—H2A	0.9500	C19—H19A	0.9800
C3—C4	1.406 (2)	C19—H19B	0.9800
C4—C5	1.373 (2)	C19—H19C	0.9800
C4—H4A	0.9500	C20—H20A	0.9800
C5—C6	1.426 (2)	C20—H20B	0.9800
C6—C7	1.426 (2)	C20—H20C	0.9800
C7—H7A	0.9500
N1—Ni—N2	85.95 (6)	N2—C9—H9B	110.5
N1—Ni—O2	177.34 (6)	C8—C9—H9B	110.5
N2—Ni—O2	94.11 (6)	H9A—C9—H9B	108.7
N1—Ni—O1	93.64 (6)	N2—C10—C11	124.68 (15)
N2—Ni—O1	176.89 (6)	N2—C10—H10A	117.7
O2—Ni—O1	86.44 (5)	C11—C10—H10A	117.7
C1—O1—Ni	126.87 (11)	C10—C11—C16	121.80 (15)
C16—O2—Ni	127.42 (10)	C10—C11—C12	119.46 (15)
C3—O3—C17	117.05 (13)	C16—C11—C12	118.73 (15)
C5—O4—C18	116.65 (13)	C13—C12—O5	123.95 (15)
C12—O5—C19	117.32 (13)	C13—C12—C11	121.68 (15)
C14—O6—C20	116.69 (13)	O5—C12—C11	114.37 (14)
C7—N1—C8	119.28 (14)	C12—C13—C14	118.19 (15)
C7—N1—Ni	127.27 (12)	C12—C13—H13A	120.9
C8—N1—Ni	113.45 (10)	C14—C13—H13A	120.9
C10—N2—C9	118.73 (13)	O6—C14—C15	123.75 (15)
C10—N2—Ni	127.03 (12)	O6—C14—C13	113.77 (15)
C9—N2—Ni	114.24 (11)	C15—C14—C13	122.48 (15)
O1—C1—C2	117.36 (14)	C14—C15—C16	119.78 (15)
O1—C1—C6	123.69 (15)	C14—C15—H15A	120.1
C2—C1—C6	118.94 (14)	C16—C15—H15A	120.1
C3—C2—C1	119.91 (15)	O2—C16—C15	117.64 (14)
C3—C2—H2A	120.0	O2—C16—C11	123.25 (15)
C1—C2—H2A	120.0	C15—C16—C11	119.11 (15)
O3—C3—C2	124.24 (16)	O3—C17—H17A	109.5
O3—C3—C4	113.82 (15)	O3—C17—H17B	109.5
C2—C3—C4	121.94 (15)	H17A—C17—H17B	109.5
C5—C4—C3	118.66 (15)	O3—C17—H17C	109.5
C5—C4—H4A	120.7	H17A—C17—H17C	109.5
C3—C4—H4A	120.7	H17B—C17—H17C	109.5
O4—C5—C4	123.50 (15)	O4—C18—H18A	109.5
O4—C5—C6	114.92 (14)	O4—C18—H18B	109.5
C4—C5—C6	121.58 (15)	H18A—C18—H18B	109.5
C1—C6—C7	121.24 (15)	O4—C18—H18C	109.5
C1—C6—C5	118.77 (15)	H18A—C18—H18C	109.5
C7—C6—C5	119.70 (15)	H18B—C18—H18C	109.5
N1—C7—C6	123.96 (15)	O5—C19—H19A	109.5
N1—C7—H7A	118.0	O5—C19—H19B	109.5
C6—C7—H7A	118.0	H19A—C19—H19B	109.5
N1—C8—C9	106.45 (13)	O5—C19—H19C	109.5
N1—C8—H8A	110.4	H19A—C19—H19C	109.5
C9—C8—H8A	110.4	H19B—C19—H19C	109.5
N1—C8—H8B	110.4	O6—C20—H20A	109.5
C9—C8—H8B	110.4	O6—C20—H20B	109.5
H8A—C8—H8B	108.6	H20A—C20—H20B	109.5
N2—C9—C8	106.22 (13)	O6—C20—H20C	109.5
N2—C9—H9A	110.5	H20A—C20—H20C	109.5
C8—C9—H9A	110.5	H20B—C20—H20C	109.5
N1—Ni—O1—C1	−16.22 (14)	O4—C5—C6—C7	−8.9 (2)
N2—Ni—O1—C1	−98.5 (11)	C4—C5—C6—C7	171.01 (15)
O2—Ni—O1—C1	161.12 (14)	C8—N1—C7—C6	171.34 (15)
N1—Ni—O2—C16	−105.1 (12)	Ni—N1—C7—C6	−8.6 (2)
N2—Ni—O2—C16	−13.82 (14)	C1—C6—C7—N1	−8.2 (3)
O1—Ni—O2—C16	163.11 (14)	C5—C6—C7—N1	177.99 (16)
N2—Ni—N1—C7	−165.37 (15)	C7—N1—C8—C9	146.29 (15)
O2—Ni—N1—C7	−73.9 (12)	Ni—N1—C8—C9	−33.74 (16)
O1—Ni—N1—C7	17.72 (15)	C10—N2—C9—C8	151.31 (15)
N2—Ni—N1—C8	14.66 (12)	Ni—N2—C9—C8	−29.43 (16)
O2—Ni—N1—C8	106.1 (12)	N1—C8—C9—N2	38.49 (17)
O1—Ni—N1—C8	−162.25 (11)	C9—N2—C10—C11	175.76 (15)
N1—Ni—N2—C10	−171.54 (15)	Ni—N2—C10—C11	−3.4 (3)
O2—Ni—N2—C10	11.12 (15)	N2—C10—C11—C16	−6.4 (3)
O1—Ni—N2—C10	−89.0 (11)	N2—C10—C11—C12	175.06 (16)
N1—Ni—N2—C9	9.28 (12)	C19—O5—C12—C13	14.1 (2)
O2—Ni—N2—C9	−168.06 (11)	C19—O5—C12—C11	−165.63 (15)
O1—Ni—N2—C9	91.8 (11)	C10—C11—C12—C13	177.11 (16)
Ni—O1—C1—C2	−175.30 (11)	C16—C11—C12—C13	−1.5 (3)
Ni—O1—C1—C6	5.7 (2)	C10—C11—C12—O5	−3.2 (2)
O1—C1—C2—C3	178.92 (15)	C16—C11—C12—O5	178.18 (14)
C6—C1—C2—C3	−2.0 (2)	O5—C12—C13—C14	−179.25 (16)
C17—O3—C3—C2	5.6 (2)	C11—C12—C13—C14	0.4 (3)
C17—O3—C3—C4	−173.47 (16)	C20—O6—C14—C15	−0.1 (3)
C1—C2—C3—O3	178.78 (15)	C20—O6—C14—C13	−179.51 (15)
C1—C2—C3—C4	−2.2 (3)	C12—C13—C14—O6	−179.43 (16)
O3—C3—C4—C5	−177.02 (15)	C12—C13—C14—C15	1.1 (3)
C2—C3—C4—C5	3.9 (2)	O6—C14—C15—C16	179.13 (16)
C18—O4—C5—C4	−1.1 (2)	C13—C14—C15—C16	−1.5 (3)
C18—O4—C5—C6	178.73 (14)	Ni—O2—C16—C15	−170.27 (11)
C3—C4—C5—O4	178.62 (15)	Ni—O2—C16—C11	8.7 (2)
C3—C4—C5—C6	−1.2 (2)	C14—C15—C16—O2	179.34 (15)
O1—C1—C6—C7	9.7 (3)	C14—C15—C16—C11	0.3 (2)
C2—C1—C6—C7	−169.32 (15)	C10—C11—C16—O2	3.6 (3)
O1—C1—C6—C5	−176.52 (15)	C12—C11—C16—O2	−177.85 (15)
C2—C1—C6—C5	4.5 (2)	C10—C11—C16—C15	−177.45 (15)
O4—C5—C6—C1	177.22 (14)	C12—C11—C16—C15	1.1 (2)
C4—C5—C6—C1	−2.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···O2i	0.99	2.61	3.587 (2)	169
C17—H17A···O4ii	0.98	2.60	3.484 (2)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯O2i	0.99	2.61	3.587 (2)	169
C17—H17A⋯O4ii	0.98	2.60	3.484 (2)	150

Symmetry codes: (i) ; (ii) .