{6,6′-Dimeth­oxy-2,2′-[4,5-dimethyl-o-phenyl­enebis(nitrilo­methyl­idyne)]diphenolato}nickel(II)

Kargar, H.; Kia, R.; Tahir, M.N.; Sahraei, A.

doi:10.1107/S1600536810035890

{6,6′-Dimethoxy-2,2′-[4,5-dimethyl-o-phenylenebis(nitrilomethylidyne)]diphenolato}nickel(II)

H. Kargar, R. Kia, M. N. Tahir and A. Sahraei

In the title Schiff base complex, [Ni(C₂₄H₂₂N₂O₄)], 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 intermolecular C—H

O hydrogen bonds and π–π interactions with a centroid–centroid distance of 3.8218 (19) Å.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810035890/su2210sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536810035890/su2210Isup2.hkl Contains datablock I

CCDC reference: 797627

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.005 Å
R factor = 0.047
wR factor = 0.124
Data-to-parameter ratio = 18.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.08 Ratio
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         14

Alert level G
PLAT128_ALERT_4_G Alternate Setting of Space-group P21/c   .......      P21/n

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

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

Comment top

Schiff base complexes are one of the most important stereochemical models in transition metal coordination chemistry, with ease of preparation and structural variations (Granovski et al., 1993). Metal derivatives of the Schiff bases have been studied extensively, and nickel(II) and copper(II) complexes play a major role in both synthetic and structurel research (Elmali et al., 2000; Blower et al., 1998).

The molecular structure of the title molecule is illustrated in Fig. 1. The bond lengths (Allen et al., 1987) and angles are within normal ranges. The geometry around the Ni^II atom is square-planar being coordinated by the N₂O₂ donor atoms of the tetradenate Schiff base ligand. The dihedral angle between the mean planes of the central aromatic ring (C9-C14) with the two outer rings (C1-C6 and C18-C23) are 7.62 (16) and 9.78 (17)°, respectively.

The crystal structure is stabilized by intermolecular C—H···O hydrogen bonds (Table 1) and π–π interactions [Cg1···Cg2ⁱ = 3.8218 (19)Å; Cg1 and Cg2 are the centroids of the C1-C6 and C9-C14 rings, respectively; symmetry code (i) -x, 2-y, -z].

Related literature top

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 top

The title compound was synthesized by adding bis(6-methoxysalicylidene)-4,5-dimethyl phenylenediamine (2 mmol) to a solution of NiCl₂^.6H₂O (2 mmol) in ethanol (30 ml). The mixture was refluxed with stirring for 30 min. The resultant red solution was filtered. Dark-red plate-like single crystals of the title compound, suitable for X-ray structure analysis, were obtained by slow evaporation at RT of a solution in ethanol over a period of several days.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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).

Figures top

	Fig. 1. The molecular structure of the title molecule, showing 40% probability displacement ellipsoids and the atom numbering scheme.
	Fig. 2. The crystal packing diagram of the title compound viewed down the c-axis showing intermolecular interactions as dashed lines.

{6,6'-Dimethoxy-2,2'-[4,5-dimethyl-o- phenylenebis(nitrilomethylidyne)]diphenolato}nickel(II) top

Crystal data top

[Ni(C₂₄H₂₂N₂O₄)]	F(000) = 960
M_r = 461.15	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0484P)² + 1.1318P] where P = (F_o² + 2F_c²)/3
5146 reflections	(Δ/σ)_max < 0.001
284 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

[Ni(C₂₄H₂₂N₂O₄)]	V = 2066.32 (16) Å³
M_r = 461.15	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.8057 (6) Å	µ = 0.97 mm⁻¹
b = 12.6514 (5) Å	T = 296 K
c = 13.0263 (6) Å	0.24 × 0.14 × 0.08 mm
β = 101.730 (2)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5146 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3179 reflections with I > 2σ(I)
T_min = 0.800, T_max = 0.926	R_int = 0.068
36150 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.03	Δρ_max = 0.48 e Å⁻³
5146 reflections	Δρ_min = −0.34 e Å⁻³
284 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1/2, y+1/2, −z+1/2; (ii) x−1/2, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	[Ni(C₂₄H₂₂N₂O₄)]
M_r	461.15
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	12.8057 (6), 12.6514 (5), 13.0263 (6)
β (°)	101.730 (2)
V (Å³)	2066.32 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.97
Crystal size (mm)	0.24 × 0.14 × 0.08

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.800, 0.926
No. of measured, independent and observed [I > 2σ(I)] reflections	36150, 5146, 3179
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.124, 1.03
No. of reflections	5146
No. of parameters	284
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.34

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXTL and PLATON (Spek, 2009).