{5,5'-Dimeth-oxy-2,2'-[4,5-dimethyl-o-phenyl-enebis(nitrilo-methyl-idyne)]diphenolato}nickel(II).

In the title Schiff base complex, [Ni(C(24)H(22)N(2)O(4))], the Ni(II) atom shows a square-planar geometry. The dihedral angles between the central benzene ring and the two outer rings are 4.79 (15) and 7.54 (15)°. In the crystal, mol-ecules are connected through inter-molecular C-H⋯O hydrogen bond, resulting in chains extending along the c axis. The crystal structure is further stabilized by inter-molecular π-π inter-actions, with centroid-centroid distances in the range 3.3760 (15)-3.7196 (17) Å.

Related literature

For background to Schiff base–metal complexes, see: Granovski et al. (1993 ▶); Blower et al. (1998 ▶). For related structures, see: Elmali et al. (2000 ▶); Kargar et al. (2010 ▶).

Experimental

Crystal data

[Ni(C24H22N2O4)]

M = 461.15

Monoclinic,

a = 11.3244 (10) Å

b = 16.5528 (19) Å

c = 12.1622 (11) Å

β = 113.261 (6)°

V = 2094.5 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.96 mm−1

T = 296 K

0.24 × 0.12 × 0.08 mm

Data collection

Stoe IPDS II Image Plate diffractometer

Absorption correction: multi-scan (MULABS in PLATON; Spek, 2009 ▶) T min = 0.872, T max = 1.000

13361 measured reflections

4799 independent reflections

3241 reflections with I > 2σ(I)

R int = 0.070

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.092

S = 0.98

4799 reflections

284 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.37 e Å−3

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810051834/pv2367sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051834/pv2367Isup2.hkl

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

[Ni(C24H22N2O4)]	F(000) = 960
Mr = 461.15	Dx = 1.462 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2525 reflections
a = 11.3244 (10) Å	θ = 2.5–29.5°
b = 16.5528 (19) Å	µ = 0.96 mm−1
c = 12.1622 (11) Å	T = 296 K
β = 113.261 (6)°	Block, red
V = 2094.5 (4) Å3	0.24 × 0.12 × 0.08 mm
Z = 4

Stoe IPDS II Image Plate diffractometer	4799 independent reflections
Radiation source: fine-focus sealed tube	3241 reflections with I > 2σ(I)
graphite	Rint = 0.070
Detector resolution: 0.15 mm pixels mm-1	θmax = 27.5°, θmin = 2.0°
ω scans	h = −14→14
Absorption correction: multi-scan (MULABS in PLATON; Spek, 2009)	k = −21→20
Tmin = 0.872, Tmax = 1.000	l = −15→11
13361 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.035P)2] where P = (Fo2 + 2Fc2)/3
4799 reflections	(Δ/σ)max < 0.001
284 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.37 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 > 2sigma(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	0.52301 (3)	0.15530 (2)	0.57365 (3)	0.03266 (10)
O1	0.67263 (16)	0.20767 (13)	0.58815 (17)	0.0422 (5)
O2	0.52566 (17)	0.11985 (13)	0.43077 (16)	0.0418 (5)
O3	1.05950 (18)	0.35630 (16)	0.7684 (2)	0.0597 (7)
O4	0.4090 (3)	−0.00753 (17)	0.0642 (2)	0.0735 (8)
N1	0.51974 (18)	0.19646 (15)	0.7148 (2)	0.0344 (5)
N2	0.37394 (18)	0.10034 (14)	0.5568 (2)	0.0346 (5)
C1	0.7477 (2)	0.25092 (18)	0.6784 (2)	0.0334 (6)
C2	0.8639 (2)	0.27954 (18)	0.6749 (2)	0.0387 (7)
H2A	0.8848	0.2664	0.6104	0.046*
C3	0.9458 (2)	0.32637 (19)	0.7655 (3)	0.0430 (7)
C4	0.9165 (3)	0.3470 (2)	0.8639 (3)	0.0519 (8)
H4A	0.9732	0.3785	0.9254	0.062*
C5	0.8052 (3)	0.3209 (2)	0.8688 (3)	0.0453 (8)
H5A	0.7853	0.3360	0.9331	0.054*
C6	0.7184 (2)	0.27109 (18)	0.7778 (2)	0.0338 (6)
C7	0.6055 (2)	0.24385 (18)	0.7899 (2)	0.0357 (6)
H7A	0.5917	0.2612	0.8566	0.043*
C8	0.4111 (2)	0.16962 (18)	0.7365 (2)	0.0357 (7)
C9	0.3808 (3)	0.1909 (2)	0.8325 (3)	0.0446 (7)
H9A	0.4343	0.2264	0.8899	0.053*
C10	0.2727 (3)	0.1607 (2)	0.8449 (3)	0.0483 (7)
C11	0.1927 (3)	0.1070 (2)	0.7575 (3)	0.0482 (8)
C12	0.2238 (2)	0.0857 (2)	0.6625 (3)	0.0453 (7)
H12A	0.1707	0.0501	0.6051	0.054*
C13	0.3324 (2)	0.11598 (18)	0.6505 (3)	0.0363 (6)
C14	0.3126 (2)	0.04987 (18)	0.4708 (3)	0.0400 (7)
H14A	0.2437	0.0221	0.4762	0.048*
C15	0.3415 (2)	0.03359 (18)	0.3702 (3)	0.0371 (6)
C16	0.2637 (3)	−0.0209 (2)	0.2821 (3)	0.0495 (8)
H16A	0.1975	−0.0472	0.2946	0.059*
C17	0.2811 (3)	−0.0367 (2)	0.1799 (3)	0.0498 (8)
H17A	0.2278	−0.0728	0.1234	0.060*
C18	0.3811 (3)	0.0025 (2)	0.1622 (3)	0.0475 (8)
C19	0.4612 (3)	0.0550 (2)	0.2466 (3)	0.0462 (7)
H19A	0.5277	0.0800	0.2331	0.055*
C20	0.4444 (2)	0.07135 (18)	0.3526 (2)	0.0354 (6)
C21	1.0950 (3)	0.3371 (3)	0.6713 (3)	0.0656 (10)
H21A	1.1776	0.3601	0.6857	0.098*
H21B	1.0322	0.3587	0.5985	0.098*
H21C	1.0990	0.2795	0.6644	0.098*
C22	0.3392 (4)	−0.0663 (3)	−0.0224 (3)	0.0770 (12)
H22A	0.3711	−0.0680	−0.0847	0.116*
H22B	0.2497	−0.0522	−0.0560	0.116*
H22C	0.3499	−0.1184	0.0151	0.116*
C23	0.2426 (3)	0.1856 (3)	0.9503 (3)	0.0672 (11)
H23A	0.3058	0.2237	0.9984	0.101*
H23B	0.2439	0.1388	0.9975	0.101*
H23C	0.1590	0.2100	0.9221	0.101*
C24	0.0704 (3)	0.0742 (3)	0.7637 (4)	0.0730 (12)
H24A	0.0351	0.0330	0.7041	0.110*
H24B	0.0092	0.1172	0.7493	0.110*
H24C	0.0895	0.0517	0.8416	0.110*

	U11	U22	U33	U12	U13	U23
Ni1	0.03026 (15)	0.0399 (2)	0.03049 (16)	−0.00596 (16)	0.01484 (12)	−0.00084 (19)
O1	0.0399 (9)	0.0571 (14)	0.0355 (11)	−0.0172 (9)	0.0211 (9)	−0.0088 (10)
O2	0.0435 (10)	0.0532 (13)	0.0317 (10)	−0.0148 (9)	0.0181 (9)	−0.0081 (10)
O3	0.0461 (11)	0.0767 (19)	0.0631 (14)	−0.0283 (11)	0.0289 (10)	−0.0166 (13)
O4	0.0989 (18)	0.078 (2)	0.0524 (15)	−0.0325 (15)	0.0394 (14)	−0.0308 (14)
N1	0.0332 (10)	0.0406 (14)	0.0335 (12)	−0.0018 (10)	0.0177 (10)	−0.0010 (11)
N2	0.0293 (10)	0.0376 (14)	0.0384 (13)	−0.0007 (9)	0.0150 (10)	0.0018 (11)
C1	0.0312 (12)	0.0367 (17)	0.0318 (14)	−0.0023 (11)	0.0122 (11)	0.0044 (12)
C2	0.0369 (13)	0.0477 (19)	0.0356 (15)	−0.0073 (12)	0.0185 (12)	−0.0032 (14)
C3	0.0364 (13)	0.047 (2)	0.0480 (17)	−0.0099 (12)	0.0192 (13)	−0.0003 (14)
C4	0.0483 (15)	0.064 (2)	0.0419 (16)	−0.0203 (16)	0.0158 (13)	−0.0151 (18)
C5	0.0468 (15)	0.056 (2)	0.0392 (16)	−0.0082 (13)	0.0231 (13)	−0.0091 (15)
C6	0.0329 (12)	0.0392 (17)	0.0305 (14)	−0.0028 (11)	0.0138 (11)	0.0018 (13)
C7	0.0395 (13)	0.0392 (17)	0.0344 (14)	0.0010 (12)	0.0209 (12)	−0.0004 (13)
C8	0.0338 (12)	0.0397 (19)	0.0392 (15)	−0.0021 (11)	0.0203 (12)	0.0029 (13)
C9	0.0430 (15)	0.0514 (19)	0.0482 (18)	−0.0059 (13)	0.0274 (14)	−0.0064 (15)
C10	0.0500 (15)	0.050 (2)	0.0586 (19)	0.0025 (15)	0.0364 (15)	0.0001 (18)
C11	0.0424 (15)	0.047 (2)	0.069 (2)	0.0002 (13)	0.0370 (16)	0.0050 (17)
C12	0.0353 (13)	0.0456 (19)	0.060 (2)	−0.0073 (13)	0.0243 (14)	−0.0015 (16)
C13	0.0322 (12)	0.0386 (17)	0.0430 (16)	0.0018 (11)	0.0201 (12)	0.0054 (14)
C14	0.0300 (12)	0.0404 (18)	0.0510 (17)	−0.0052 (12)	0.0176 (12)	−0.0004 (15)
C15	0.0337 (13)	0.0353 (17)	0.0409 (16)	0.0015 (11)	0.0135 (12)	−0.0026 (13)
C16	0.0381 (14)	0.048 (2)	0.060 (2)	−0.0085 (13)	0.0173 (15)	−0.0112 (17)
C17	0.0460 (16)	0.046 (2)	0.0474 (19)	−0.0041 (14)	0.0079 (14)	−0.0147 (16)
C18	0.0559 (17)	0.045 (2)	0.0410 (18)	−0.0002 (15)	0.0185 (15)	−0.0089 (15)
C19	0.0530 (16)	0.048 (2)	0.0401 (16)	−0.0102 (15)	0.0214 (14)	−0.0059 (15)
C20	0.0377 (13)	0.0348 (17)	0.0302 (14)	0.0000 (11)	0.0097 (12)	−0.0008 (12)
C21	0.0509 (16)	0.086 (3)	0.071 (2)	−0.0267 (19)	0.0368 (17)	−0.017 (2)
C22	0.094 (3)	0.081 (3)	0.053 (2)	−0.019 (2)	0.026 (2)	−0.029 (2)
C23	0.069 (2)	0.082 (3)	0.075 (3)	−0.0068 (19)	0.054 (2)	−0.009 (2)
C24	0.0556 (19)	0.082 (3)	0.103 (3)	−0.0189 (19)	0.055 (2)	−0.010 (2)

Ni1—O2	1.8456 (19)	C10—C11	1.407 (5)
Ni1—O1	1.8485 (17)	C10—C23	1.508 (4)
Ni1—N2	1.856 (2)	C11—C12	1.380 (4)
Ni1—N1	1.861 (2)	C11—C24	1.517 (4)
O1—C1	1.305 (3)	C12—C13	1.388 (3)
O2—C20	1.306 (3)	C12—H12A	0.9300
O3—C3	1.367 (3)	C14—C15	1.411 (4)
O3—C21	1.425 (4)	C14—H14A	0.9300
O4—C18	1.358 (4)	C15—C20	1.411 (4)
O4—C22	1.422 (4)	C15—C16	1.412 (4)
N1—C7	1.301 (3)	C16—C17	1.358 (4)
N1—C8	1.428 (3)	C16—H16A	0.9300
N2—C14	1.304 (4)	C17—C18	1.395 (4)
N2—C13	1.417 (3)	C17—H17A	0.9300
C1—C6	1.414 (4)	C18—C19	1.376 (4)
C1—C2	1.416 (3)	C19—C20	1.402 (4)
C2—C3	1.367 (4)	C19—H19A	0.9300
C2—H2A	0.9300	C21—H21A	0.9600
C3—C4	1.404 (4)	C21—H21B	0.9600
C4—C5	1.356 (4)	C21—H21C	0.9600
C4—H4A	0.9300	C22—H22A	0.9600
C5—C6	1.417 (4)	C22—H22B	0.9600
C5—H5A	0.9300	C22—H22C	0.9600
C6—C7	1.417 (3)	C23—H23A	0.9600
C7—H7A	0.9300	C23—H23B	0.9600
C8—C9	1.386 (4)	C23—H23C	0.9600
C8—C13	1.393 (4)	C24—H24A	0.9600
C9—C10	1.384 (4)	C24—H24B	0.9600
C9—H9A	0.9300	C24—H24C	0.9600
Cg1···Cg2i	3.4737 (17)	Cg3···Cg3i	3.3760 (15)
Cg2···Cg3i	3.7196 (17)
O2—Ni1—O1	83.33 (8)	C11—C12—H12A	119.1
O2—Ni1—N2	95.32 (9)	C13—C12—H12A	119.1
O1—Ni1—N2	178.38 (10)	C12—C13—C8	118.8 (3)
O2—Ni1—N1	177.06 (10)	C12—C13—N2	127.4 (3)
O1—Ni1—N1	95.26 (9)	C8—C13—N2	113.8 (2)
N2—Ni1—N1	86.13 (10)	N2—C14—C15	125.9 (2)
C1—O1—Ni1	127.25 (17)	N2—C14—H14A	117.1
C20—O2—Ni1	127.75 (17)	C15—C14—H14A	117.1
C3—O3—C21	117.9 (2)	C14—C15—C20	122.3 (2)
C18—O4—C22	118.7 (3)	C14—C15—C16	119.4 (3)
C7—N1—C8	121.1 (2)	C20—C15—C16	118.2 (3)
C7—N1—Ni1	125.95 (18)	C17—C16—C15	123.1 (3)
C8—N1—Ni1	112.92 (17)	C17—C16—H16A	118.5
C14—N2—C13	121.4 (2)	C15—C16—H16A	118.5
C14—N2—Ni1	125.10 (19)	C16—C17—C18	118.1 (3)
C13—N2—Ni1	113.45 (18)	C16—C17—H17A	121.0
O1—C1—C6	123.7 (2)	C18—C17—H17A	121.0
O1—C1—C2	117.5 (2)	O4—C18—C19	114.7 (3)
C6—C1—C2	118.8 (2)	O4—C18—C17	124.2 (3)
C3—C2—C1	120.5 (3)	C19—C18—C17	121.0 (3)
C3—C2—H2A	119.7	C18—C19—C20	121.2 (3)
C1—C2—H2A	119.7	C18—C19—H19A	119.4
C2—C3—O3	123.9 (3)	C20—C19—H19A	119.4
C2—C3—C4	120.8 (2)	O2—C20—C19	118.4 (3)
O3—C3—C4	115.3 (3)	O2—C20—C15	123.3 (2)
C5—C4—C3	119.8 (3)	C19—C20—C15	118.3 (3)
C5—C4—H4A	120.1	O3—C21—H21A	109.5
C3—C4—H4A	120.1	O3—C21—H21B	109.5
C4—C5—C6	121.4 (3)	H21A—C21—H21B	109.5
C4—C5—H5A	119.3	O3—C21—H21C	109.5
C6—C5—H5A	119.3	H21A—C21—H21C	109.5
C1—C6—C7	122.6 (2)	H21B—C21—H21C	109.5
C1—C6—C5	118.7 (2)	O4—C22—H22A	109.5
C7—C6—C5	118.7 (3)	O4—C22—H22B	109.5
N1—C7—C6	125.0 (3)	H22A—C22—H22B	109.5
N1—C7—H7A	117.5	O4—C22—H22C	109.5
C6—C7—H7A	117.5	H22A—C22—H22C	109.5
C9—C8—C13	119.8 (2)	H22B—C22—H22C	109.5
C9—C8—N1	126.5 (3)	C10—C23—H23A	109.5
C13—C8—N1	113.7 (2)	C10—C23—H23B	109.5
C10—C9—C8	121.6 (3)	H23A—C23—H23B	109.5
C10—C9—H9A	119.2	C10—C23—H23C	109.5
C8—C9—H9A	119.2	H23A—C23—H23C	109.5
C9—C10—C11	118.6 (3)	H23B—C23—H23C	109.5
C9—C10—C23	120.0 (3)	C11—C24—H24A	109.5
C11—C10—C23	121.3 (3)	C11—C24—H24B	109.5
C12—C11—C10	119.5 (3)	H24A—C24—H24B	109.5
C12—C11—C24	119.3 (3)	C11—C24—H24C	109.5
C10—C11—C24	121.1 (3)	H24A—C24—H24C	109.5
C11—C12—C13	121.7 (3)	H24B—C24—H24C	109.5
O2—Ni1—O1—C1	−177.0 (3)	C8—C9—C10—C11	0.1 (5)
N1—Ni1—O1—C1	5.6 (3)	C8—C9—C10—C23	−179.7 (3)
O1—Ni1—O2—C20	178.4 (2)	C9—C10—C11—C12	0.2 (5)
N2—Ni1—O2—C20	−0.7 (2)	C23—C10—C11—C12	−179.9 (3)
O1—Ni1—N1—C7	−1.8 (3)	C9—C10—C11—C24	−177.7 (3)
N2—Ni1—N1—C7	177.3 (3)	C23—C10—C11—C24	2.1 (5)
O1—Ni1—N1—C8	179.12 (19)	C10—C11—C12—C13	−0.1 (5)
N2—Ni1—N1—C8	−1.71 (19)	C24—C11—C12—C13	177.9 (3)
O2—Ni1—N2—C14	5.4 (2)	C11—C12—C13—C8	−0.4 (5)
N1—Ni1—N2—C14	−177.1 (2)	C11—C12—C13—N2	−178.7 (3)
O2—Ni1—N2—C13	−176.57 (19)	C9—C8—C13—C12	0.7 (4)
N1—Ni1—N2—C13	0.86 (19)	N1—C8—C13—C12	179.9 (2)
Ni1—O1—C1—C6	−6.3 (4)	C9—C8—C13—N2	179.3 (3)
Ni1—O1—C1—C2	174.40 (19)	N1—C8—C13—N2	−1.6 (4)
O1—C1—C2—C3	178.8 (3)	C14—N2—C13—C12	−3.3 (5)
C6—C1—C2—C3	−0.5 (4)	Ni1—N2—C13—C12	178.6 (2)
C1—C2—C3—O3	−179.9 (3)	C14—N2—C13—C8	178.3 (3)
C1—C2—C3—C4	0.0 (5)	Ni1—N2—C13—C8	0.2 (3)
C21—O3—C3—C2	−0.3 (5)	C13—N2—C14—C15	176.1 (3)
C21—O3—C3—C4	179.7 (3)	Ni1—N2—C14—C15	−6.0 (4)
C2—C3—C4—C5	−0.6 (5)	N2—C14—C15—C20	0.5 (5)
O3—C3—C4—C5	179.4 (3)	N2—C14—C15—C16	−178.0 (3)
C3—C4—C5—C6	1.7 (5)	C14—C15—C16—C17	176.6 (3)
O1—C1—C6—C7	1.9 (5)	C20—C15—C16—C17	−2.0 (5)
C2—C1—C6—C7	−178.8 (3)	C15—C16—C17—C18	0.4 (5)
O1—C1—C6—C5	−177.8 (3)	C22—O4—C18—C19	174.1 (3)
C2—C1—C6—C5	1.6 (4)	C22—O4—C18—C17	−5.2 (5)
C4—C5—C6—C1	−2.2 (5)	C16—C17—C18—O4	−179.8 (3)
C4—C5—C6—C7	178.2 (3)	C16—C17—C18—C19	1.0 (5)
C8—N1—C7—C6	177.6 (3)	O4—C18—C19—C20	−179.9 (3)
Ni1—N1—C7—C6	−1.4 (4)	C17—C18—C19—C20	−0.7 (5)
C1—C6—C7—N1	2.1 (5)	Ni1—O2—C20—C19	177.2 (2)
C5—C6—C7—N1	−178.3 (3)	Ni1—O2—C20—C15	−3.8 (4)
C7—N1—C8—C9	2.2 (5)	C18—C19—C20—O2	178.1 (3)
Ni1—N1—C8—C9	−178.7 (3)	C18—C19—C20—C15	−1.0 (5)
C7—N1—C8—C13	−176.9 (3)	C14—C15—C20—O2	4.7 (4)
Ni1—N1—C8—C13	2.2 (3)	C16—C15—C20—O2	−176.8 (3)
C13—C8—C9—C10	−0.6 (5)	C14—C15—C20—C19	−176.3 (3)
N1—C8—C9—C10	−179.6 (3)	C16—C15—C20—C19	2.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O2ii	0.93	2.41	3.173 (3)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯O2i	0.93	2.41	3.173 (3)	140

Symmetry code: (i) .