{6,6'-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 has a slightly distorted square-planar coordination environment. The dihedral angles between the central benzene ring and the two outer rings are 7.62 (16) and 9.78 (17)°. The crystal structure is stabilized by inter-molecular C-H⋯O hydrogen bonds and π-π inter-actions with a centroid-centroid distance of 3.8218 (19) Å.

Related literature

For background to Schiff base–metal complexes, see: Granovski et al. (1993 ▶); Blower et al. (1998 ▶); Elmali et al. (2000 ▶). For standard values of bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

[Ni(C24H22N2O4)]

M = 461.15

Monoclinic,

a = 12.8057 (6) Å

b = 12.6514 (5) Å

c = 13.0263 (6) Å

β = 101.730 (2)°

V = 2066.32 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.97 mm−1

T = 296 K

0.24 × 0.14 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.800, T max = 0.926

36150 measured reflections

5146 independent reflections

3179 reflections with I > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.124

S = 1.03

5146 reflections

284 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; 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/S1600536810035890/su2210sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035890/su2210Isup2.hkl

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

[Ni(C24H22N2O4)]	F(000) = 960
Mr = 461.15	Dx = 1.482 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2525 reflections
a = 12.8057 (6) Å	θ = 2.5–29.5°
b = 12.6514 (5) Å	µ = 0.97 mm−1
c = 13.0263 (6) Å	T = 296 K
β = 101.730 (2)°	Plate, red
V = 2066.32 (16) Å3	0.24 × 0.14 × 0.08 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	5146 independent reflections
Radiation source: fine-focus sealed tube	3179 reflections with I > 2σ(I)
graphite	Rint = 0.068
φ and ω scans	θmax = 28.4°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −17→17
Tmin = 0.800, Tmax = 0.926	k = −16→16
36150 measured reflections	l = −17→17

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0484P)2 + 1.1318P] where P = (Fo2 + 2Fc2)/3
5146 reflections	(Δ/σ)max < 0.001
284 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.34 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	0.01614 (3)	0.78355 (3)	0.17262 (3)	0.03619 (14)
O1	0.07749 (19)	0.88142 (16)	0.27017 (17)	0.0481 (6)
O2	0.21622 (19)	1.12212 (16)	0.05147 (18)	0.0483 (6)
O3	−0.02481 (18)	0.72048 (16)	0.28477 (17)	0.0453 (5)
O4	−0.2538 (2)	0.4558 (2)	0.1089 (2)	0.0768 (9)
N1	0.06210 (19)	0.84778 (18)	0.06261 (19)	0.0346 (6)
N2	−0.0465 (2)	0.68259 (19)	0.07723 (19)	0.0364 (6)
C1	0.1314 (3)	0.9655 (2)	0.2565 (3)	0.0410 (7)
C2	0.1766 (3)	1.0258 (3)	0.3455 (3)	0.0506 (9)
H2	0.1675	1.0047	0.4115	0.061*
C3	0.2336 (3)	1.1150 (3)	0.3353 (3)	0.0528 (9)
H3	0.2638	1.1528	0.3953	0.063*
C4	0.2480 (3)	1.1515 (3)	0.2381 (3)	0.0506 (9)
H4	0.2863	1.2131	0.2332	0.061*
C5	0.2054 (3)	1.0954 (2)	0.1504 (3)	0.0398 (7)
C6	0.1472 (2)	0.9993 (2)	0.1570 (2)	0.0365 (7)
C7	0.2852 (3)	1.2086 (3)	0.0418 (3)	0.0536 (9)
H7A	0.2584	1.2717	0.0683	0.080*
H7B	0.2880	1.2184	−0.0307	0.080*
H7C	0.3555	1.1939	0.0813	0.080*
C8	0.1120 (2)	0.9388 (2)	0.0659 (2)	0.0367 (7)
H8	0.1252	0.9652	0.0031	0.044*
C9	0.0357 (2)	0.7889 (2)	−0.0328 (2)	0.0349 (7)
C10	0.0623 (3)	0.8146 (2)	−0.1274 (2)	0.0398 (7)
H10	0.1035	0.8743	−0.1319	0.048*
C11	0.0285 (3)	0.7528 (3)	−0.2154 (3)	0.0417 (7)
C12	−0.0325 (3)	0.6620 (2)	−0.2082 (2)	0.0407 (7)
C13	−0.0573 (3)	0.6355 (2)	−0.1132 (3)	0.0421 (8)
H13	−0.0966	0.5746	−0.1080	0.050*
C14	−0.0241 (2)	0.6985 (2)	−0.0250 (2)	0.0347 (7)
C15	0.0579 (3)	0.7840 (3)	−0.3177 (3)	0.0583 (10)
H15A	0.0972	0.8491	−0.3086	0.087*
H15B	−0.0058	0.7932	−0.3703	0.087*
H15C	0.1010	0.7295	−0.3394	0.087*
C16	−0.0759 (3)	0.5964 (3)	−0.3041 (3)	0.0534 (9)
H16A	−0.1054	0.5320	−0.2833	0.080*
H16B	−0.0194	0.5800	−0.3399	0.080*
H16C	−0.1306	0.6353	−0.3501	0.080*
C17	−0.1087 (3)	0.6065 (2)	0.0954 (2)	0.0405 (7)
H17	−0.1382	0.5632	0.0393	0.049*
C18	−0.1353 (3)	0.5845 (2)	0.1932 (3)	0.0406 (7)
C19	−0.2085 (3)	0.5008 (3)	0.2020 (3)	0.0520 (9)
C20	−0.2290 (3)	0.4723 (3)	0.2968 (3)	0.0583 (10)
H20	−0.2767	0.4180	0.3016	0.070*
C21	−0.1776 (3)	0.5255 (3)	0.3863 (3)	0.0554 (10)
H21	−0.1906	0.5049	0.4511	0.067*
C22	−0.1088 (3)	0.6069 (3)	0.3820 (3)	0.0514 (9)
H22	−0.0758	0.6408	0.4435	0.062*
C23	−0.0873 (3)	0.6399 (2)	0.2851 (3)	0.0420 (8)
C24	−0.3272 (5)	0.3705 (4)	0.1122 (4)	0.107 (2)
H24A	−0.2894	0.3109	0.1473	0.161*
H24B	−0.3606	0.3507	0.0420	0.161*
H24C	−0.3808	0.3928	0.1495	0.161*

	U11	U22	U33	U12	U13	U23
Ni1	0.0430 (3)	0.0344 (2)	0.0338 (2)	−0.00055 (18)	0.01401 (17)	−0.00004 (17)
O1	0.0676 (16)	0.0428 (12)	0.0370 (13)	−0.0083 (11)	0.0177 (12)	−0.0029 (10)
O2	0.0570 (15)	0.0408 (12)	0.0511 (15)	−0.0117 (11)	0.0203 (12)	−0.0070 (10)
O3	0.0599 (14)	0.0443 (12)	0.0366 (12)	−0.0058 (11)	0.0210 (11)	0.0005 (10)
O4	0.096 (2)	0.0802 (18)	0.0535 (17)	−0.0504 (17)	0.0144 (16)	0.0106 (15)
N1	0.0350 (14)	0.0370 (13)	0.0337 (14)	−0.0019 (10)	0.0117 (11)	−0.0013 (11)
N2	0.0425 (15)	0.0360 (12)	0.0342 (14)	−0.0006 (11)	0.0158 (12)	0.0034 (11)
C1	0.0447 (19)	0.0377 (16)	0.0426 (19)	0.0038 (14)	0.0134 (15)	−0.0060 (14)
C2	0.066 (2)	0.0485 (19)	0.038 (2)	0.0014 (17)	0.0135 (18)	−0.0058 (15)
C3	0.058 (2)	0.053 (2)	0.045 (2)	−0.0070 (17)	0.0061 (18)	−0.0139 (17)
C4	0.052 (2)	0.0418 (17)	0.058 (2)	−0.0081 (15)	0.0113 (18)	−0.0122 (16)
C5	0.0378 (18)	0.0377 (16)	0.046 (2)	0.0018 (13)	0.0135 (15)	−0.0065 (14)
C6	0.0364 (17)	0.0322 (14)	0.0420 (19)	0.0041 (12)	0.0108 (14)	−0.0040 (13)
C7	0.055 (2)	0.0467 (18)	0.064 (2)	−0.0115 (17)	0.0230 (19)	−0.0006 (17)
C8	0.0363 (17)	0.0362 (15)	0.0401 (18)	0.0016 (13)	0.0140 (14)	0.0005 (13)
C9	0.0370 (17)	0.0349 (14)	0.0345 (16)	−0.0018 (13)	0.0114 (13)	−0.0044 (13)
C10	0.0441 (19)	0.0398 (16)	0.0375 (18)	−0.0058 (14)	0.0129 (15)	−0.0011 (13)
C11	0.0430 (19)	0.0481 (17)	0.0375 (18)	0.0019 (14)	0.0160 (15)	−0.0002 (14)
C12	0.0450 (19)	0.0423 (17)	0.0376 (18)	−0.0009 (14)	0.0148 (15)	−0.0058 (14)
C13	0.045 (2)	0.0382 (16)	0.047 (2)	−0.0091 (14)	0.0181 (16)	−0.0056 (14)
C14	0.0340 (17)	0.0364 (15)	0.0358 (17)	−0.0010 (12)	0.0117 (13)	0.0018 (12)
C15	0.070 (2)	0.065 (2)	0.045 (2)	−0.015 (2)	0.0241 (19)	−0.0027 (18)
C16	0.059 (2)	0.059 (2)	0.045 (2)	−0.0130 (18)	0.0163 (18)	−0.0120 (17)
C17	0.0442 (19)	0.0403 (16)	0.0381 (18)	−0.0054 (14)	0.0107 (15)	0.0023 (14)
C18	0.0422 (19)	0.0401 (16)	0.0425 (19)	0.0005 (14)	0.0156 (15)	0.0092 (14)
C19	0.058 (2)	0.0480 (19)	0.052 (2)	−0.0087 (17)	0.0170 (19)	0.0094 (17)
C20	0.061 (2)	0.055 (2)	0.064 (3)	−0.0059 (18)	0.026 (2)	0.0199 (19)
C21	0.070 (3)	0.052 (2)	0.054 (2)	0.0074 (19)	0.034 (2)	0.0134 (18)
C22	0.068 (2)	0.0470 (19)	0.046 (2)	0.0061 (17)	0.0270 (19)	0.0053 (16)
C23	0.048 (2)	0.0387 (16)	0.0425 (19)	0.0098 (14)	0.0174 (16)	0.0082 (14)
C24	0.139 (5)	0.113 (4)	0.066 (3)	−0.090 (4)	0.013 (3)	0.008 (3)

Ni1—O3	1.832 (2)	C9—C14	1.391 (4)
Ni1—O1	1.833 (2)	C10—C11	1.382 (4)
Ni1—N1	1.845 (2)	C10—H10	0.9300
Ni1—N2	1.848 (2)	C11—C12	1.402 (4)
O1—C1	1.299 (4)	C11—C15	1.509 (4)
O2—C5	1.367 (4)	C12—C13	1.380 (4)
O2—C7	1.428 (4)	C12—C16	1.509 (4)
O3—C23	1.297 (4)	C13—C14	1.392 (4)
O4—C19	1.358 (4)	C13—H13	0.9300
O4—C24	1.438 (4)	C15—H15A	0.9600
N1—C8	1.313 (4)	C15—H15B	0.9600
N1—C9	1.430 (4)	C15—H15C	0.9600
N2—C17	1.302 (4)	C16—H16A	0.9600
N2—C14	1.433 (4)	C16—H16B	0.9600
C1—C2	1.410 (4)	C16—H16C	0.9600
C1—C6	1.419 (4)	C17—C18	1.411 (4)
C2—C3	1.365 (5)	C17—H17	0.9300
C2—H2	0.9300	C18—C23	1.415 (4)
C3—C4	1.395 (5)	C18—C19	1.434 (4)
C3—H3	0.9300	C19—C20	1.363 (5)
C4—C5	1.361 (4)	C20—C21	1.390 (5)
C4—H4	0.9300	C20—H20	0.9300
C5—C6	1.437 (4)	C21—C22	1.364 (5)
C6—C8	1.407 (4)	C21—H21	0.9300
C7—H7A	0.9600	C22—C23	1.409 (4)
C7—H7B	0.9600	C22—H22	0.9300
C7—H7C	0.9600	C24—H24A	0.9600
C8—H8	0.9300	C24—H24B	0.9600
C9—C10	1.382 (4)	C24—H24C	0.9600
O3—Ni1—O1	83.87 (9)	C10—C11—C15	119.5 (3)
O3—Ni1—N1	177.97 (11)	C12—C11—C15	121.0 (3)
O1—Ni1—N1	94.67 (10)	C13—C12—C11	119.4 (3)
O3—Ni1—N2	94.57 (10)	C13—C12—C16	119.7 (3)
O1—Ni1—N2	178.42 (10)	C11—C12—C16	120.8 (3)
N1—Ni1—N2	86.88 (10)	C12—C13—C14	120.9 (3)
C1—O1—Ni1	128.5 (2)	C12—C13—H13	119.6
C5—O2—C7	117.1 (3)	C14—C13—H13	119.6
C23—O3—Ni1	128.4 (2)	C9—C14—C13	119.4 (3)
C19—O4—C24	116.8 (3)	C9—C14—N2	113.6 (3)
C8—N1—C9	120.8 (3)	C13—C14—N2	127.0 (3)
C8—N1—Ni1	126.2 (2)	C11—C15—H15A	109.5
C9—N1—Ni1	112.93 (18)	C11—C15—H15B	109.5
C17—N2—C14	121.3 (3)	H15A—C15—H15B	109.5
C17—N2—Ni1	125.9 (2)	C11—C15—H15C	109.5
C14—N2—Ni1	112.73 (18)	H15A—C15—H15C	109.5
O1—C1—C2	118.1 (3)	H15B—C15—H15C	109.5
O1—C1—C6	123.4 (3)	C12—C16—H16A	109.5
C2—C1—C6	118.5 (3)	C12—C16—H16B	109.5
C3—C2—C1	120.4 (3)	H16A—C16—H16B	109.5
C3—C2—H2	119.8	C12—C16—H16C	109.5
C1—C2—H2	119.8	H16A—C16—H16C	109.5
C2—C3—C4	122.2 (3)	H16B—C16—H16C	109.5
C2—C3—H3	118.9	N2—C17—C18	125.4 (3)
C4—C3—H3	118.9	N2—C17—H17	117.3
C5—C4—C3	119.0 (3)	C18—C17—H17	117.3
C5—C4—H4	120.5	C17—C18—C23	121.5 (3)
C3—C4—H4	120.5	C17—C18—C19	120.0 (3)
C4—C5—O2	124.2 (3)	C23—C18—C19	118.5 (3)
C4—C5—C6	121.0 (3)	O4—C19—C20	124.9 (3)
O2—C5—C6	114.7 (3)	O4—C19—C18	113.9 (3)
C8—C6—C1	121.7 (3)	C20—C19—C18	121.2 (3)
C8—C6—C5	119.4 (3)	C19—C20—C21	119.1 (3)
C1—C6—C5	118.8 (3)	C19—C20—H20	120.4
O2—C7—H7A	109.5	C21—C20—H20	120.4
O2—C7—H7B	109.5	C22—C21—C20	122.1 (3)
H7A—C7—H7B	109.5	C22—C21—H21	119.0
O2—C7—H7C	109.5	C20—C21—H21	119.0
H7A—C7—H7C	109.5	C21—C22—C23	120.4 (4)
H7B—C7—H7C	109.5	C21—C22—H22	119.8
N1—C8—C6	125.1 (3)	C23—C22—H22	119.8
N1—C8—H8	117.5	O3—C23—C22	118.0 (3)
C6—C8—H8	117.5	O3—C23—C18	123.3 (3)
C10—C9—C14	119.8 (3)	C22—C23—C18	118.7 (3)
C10—C9—N1	126.5 (3)	O4—C24—H24A	109.5
C14—C9—N1	113.7 (3)	O4—C24—H24B	109.5
C9—C10—C11	120.9 (3)	H24A—C24—H24B	109.5
C9—C10—H10	119.5	O4—C24—H24C	109.5
C11—C10—H10	119.5	H24A—C24—H24C	109.5
C10—C11—C12	119.5 (3)	H24B—C24—H24C	109.5
O3—Ni1—O1—C1	179.7 (3)	C9—C10—C11—C12	−0.8 (5)
N1—Ni1—O1—C1	1.2 (3)	C9—C10—C11—C15	179.3 (3)
O1—Ni1—O3—C23	173.2 (3)	C10—C11—C12—C13	−0.4 (5)
N2—Ni1—O3—C23	−7.1 (3)	C15—C11—C12—C13	179.5 (3)
O1—Ni1—N1—C8	−5.6 (3)	C10—C11—C12—C16	176.5 (3)
N2—Ni1—N1—C8	174.6 (3)	C15—C11—C12—C16	−3.6 (5)
O1—Ni1—N1—C9	175.77 (19)	C11—C12—C13—C14	1.1 (5)
N2—Ni1—N1—C9	−4.0 (2)	C16—C12—C13—C14	−175.8 (3)
O3—Ni1—N2—C17	8.2 (3)	C10—C9—C14—C13	−0.6 (4)
N1—Ni1—N2—C17	−173.2 (3)	N1—C9—C14—C13	178.5 (3)
O3—Ni1—N2—C14	−174.79 (19)	C10—C9—C14—N2	−179.4 (3)
N1—Ni1—N2—C14	3.8 (2)	N1—C9—C14—N2	−0.3 (4)
Ni1—O1—C1—C2	−176.2 (2)	C12—C13—C14—C9	−0.6 (5)
Ni1—O1—C1—C6	3.6 (5)	C12—C13—C14—N2	177.9 (3)
O1—C1—C2—C3	−179.7 (3)	C17—N2—C14—C9	174.4 (3)
C6—C1—C2—C3	0.4 (5)	Ni1—N2—C14—C9	−2.8 (3)
C1—C2—C3—C4	1.2 (6)	C17—N2—C14—C13	−4.3 (5)
C2—C3—C4—C5	−1.1 (5)	Ni1—N2—C14—C13	178.5 (3)
C3—C4—C5—O2	−178.6 (3)	C14—N2—C17—C18	179.8 (3)
C3—C4—C5—C6	−0.7 (5)	Ni1—N2—C17—C18	−3.4 (5)
C7—O2—C5—C4	6.2 (5)	N2—C17—C18—C23	−5.6 (5)
C7—O2—C5—C6	−171.8 (3)	N2—C17—C18—C19	177.4 (3)
O1—C1—C6—C8	−5.1 (5)	C24—O4—C19—C20	−1.2 (6)
C2—C1—C6—C8	174.8 (3)	C24—O4—C19—C18	179.3 (4)
O1—C1—C6—C5	178.1 (3)	C17—C18—C19—O4	−5.8 (5)
C2—C1—C6—C5	−2.1 (4)	C23—C18—C19—O4	177.2 (3)
C4—C5—C6—C8	−174.6 (3)	C17—C18—C19—C20	174.7 (3)
O2—C5—C6—C8	3.4 (4)	C23—C18—C19—C20	−2.3 (5)
C4—C5—C6—C1	2.3 (5)	O4—C19—C20—C21	−179.5 (4)
O2—C5—C6—C1	−179.7 (3)	C18—C19—C20—C21	−0.1 (6)
C9—N1—C8—C6	−175.9 (3)	C19—C20—C21—C22	1.3 (6)
Ni1—N1—C8—C6	5.6 (4)	C20—C21—C22—C23	−0.1 (5)
C1—C6—C8—N1	0.3 (5)	Ni1—O3—C23—C22	−178.7 (2)
C5—C6—C8—N1	177.1 (3)	Ni1—O3—C23—C18	0.8 (4)
C8—N1—C9—C10	3.6 (5)	C21—C22—C23—O3	177.2 (3)
Ni1—N1—C9—C10	−177.7 (3)	C21—C22—C23—C18	−2.4 (5)
C8—N1—C9—C14	−175.4 (3)	C17—C18—C23—O3	7.0 (5)
Ni1—N1—C9—C14	3.3 (3)	C19—C18—C23—O3	−176.0 (3)
C14—C9—C10—C11	1.3 (5)	C17—C18—C23—C22	−173.5 (3)
N1—C9—C10—C11	−177.6 (3)	C19—C18—C23—C22	3.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7C···O3i	0.96	2.51	3.424 (5)	158
C21—H21···O2ii	0.93	2.52	3.340 (4)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7C⋯O3i	0.96	2.51	3.424 (5)	158
C21—H21⋯O2ii	0.93	2.52	3.340 (4)	147

Symmetry codes: (i) ; (ii) .