{4,4′-Dimeth­oxy-2,2′-[2,2-dimethyl­propane-1,3-diylbis(nitrilo­methyl­idyne)]diphenolato}nickel(II)

Montazerozohori, M.; Habibi, M.H.; Mokhtari, R.; Yamane, Y.; Suzuki, T.

doi:10.1107/S1600536809019965

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page m703

doi:10.1107/S1600536809019965

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{4,4′-Dimethoxy-2,2′-[2,2-dimethylpropane-1,3-diylbis(nitrilomethylidyne)]diphenolato}nickel(II)

Morteza Montazerozohori,^a Mohammad Hossein Habibi,^b ^* Reza Mokhtari,^b Yuki Yamane ^c and Takayoshi Suzuki ^c

^aDepartment of Chemistry, Yasouj University, Yasouj 75914-353, Iran, ^bCatalysis Division, Department of Chemistry, University of Isfahan, Isfahan 81746-73441, Iran, and ^cDepartment of Chemistry, Faculty of Science, Okayama University, Tsushima-naka 3-1-1, Okayama 700-8530, Japan
^*Correspondence e-mail: mhhabibi@yahoo.com

(Received 24 May 2009; accepted 26 May 2009; online 6 June 2009)

In the title complex, [Ni(C₂₁H₂₄N₂O₄)], the Ni^II ion has a slightly distorted square-planar geometry, coordinated by the two N and two O atoms of a new tetradentate Schiff base ligand. The dihedral angle between the planes of the two NiNC₃O 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_r = 427.13
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.026
wR(F²) = 0.071
S = 1.05
4362 reflections
258 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −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.

Supporting information

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

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

checkCIF report

Comment top

Schiff bases and their biologically active complexes have been studied extensively over the past decade. Although numerous transition metal complexes of Schiff bases have been structurally characterized, relatively few free Schiff bases have been similarly characterized (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).

Recently we reported the structure of a copper(II) and nickel(II) complexes with the N,N'-bis(6-methoxysalicylidene)-1,3-diaminopropane ligand (Habibi et al., 2007a,b). The title compound is isostructural with its Cu^II and Ni^II analogues.

In the title compound (Figure 1), the Ni—O and Ni—N distances are larger than the comparable mean distances of 1.829 and 1.859 Å (Table 1), respectively, in N,N'-ethylenebis(salicylideneiminato)nickel(II) (Shkolnikova et al., 1970) and 1.849 (2) and 1.840 (2) Å, respectively, in N,N'-ethylenebis[(2-hydroxy-1-naphthyl)methaniminato]nickel(II) (Akhtar, 1981).

Related literature top

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 top

A mixture of 6-methoxysalicylaldehyde (2.0 mmol, 304 mg) and 2,2-dimethylpropane-1,3-diamine (1.0 mmol, 102 mg) was dissolved in methanol (10 ml) with stirring for 15 min at room temperature, to give a clear yellow solution. A methanol solution (10 ml) of Ni(OAc)₂.4H₂O (1.0 mmol, 249 mg) was then added. The mixture was refluxed for a further 45 min and then filtered. After keeping the filtrate in air for 5 d, dark green block-shaped crystals were formed at the bottom of the vessel on slow evaporation of the solvent, in about 85% yield.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); 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 (Sheldrick, 2008).

Figures top

Fig. 1. A view of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.

{4,4'-Dimethoxy-2,2'-[2,2-dimethylpropane-1,3- diylbis(nitrilomethylidyne)]diphenolato}nickel(II) top

Crystal data top

[Ni(C₂₁H₂₄N₂O₄)]	D_x = 1.487 Mg m⁻³
M_r = 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

Data collection top

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

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.071	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0413P)² + 1.3733P] where P = (F_o² + 2F_c²)/3
4362 reflections	(Δ/σ)_max = 0.001
258 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

[Ni(C₂₁H₂₄N₂O₄)]	V = 3815.5 (3) Å³
M_r = 427.13	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 15.6110 (7) Å	µ = 1.05 mm⁻¹
b = 9.1151 (5) Å	T = 193 K
c = 26.8142 (12) Å	0.30 × 0.20 × 0.20 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	4362 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3946 reflections with I > 2σ(I)
T_min = 0.744, T_max = 0.818	R_int = 0.020
35644 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	0 restraints
wR(F²) = 0.071	H-atom parameters constrained
S = 1.05	Δρ_max = 0.43 e Å⁻³
4362 reflections	Δρ_min = −0.18 e Å⁻³
258 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	[Ni(C₂₁H₂₄N₂O₄)]
M_r	427.13
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	193
a, b, c (Å)	15.6110 (7), 9.1151 (5), 26.8142 (12)
V (Å³)	3815.5 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.05
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.744, 0.818
No. of measured, independent and observed [I > 2σ(I)] reflections	35644, 4362, 3946
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.071, 1.05
No. of reflections	4362
No. of parameters	258
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.18

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Acknowledgements

We thank Yasouj University and the University of Isfahan for partial support of this work.

References

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