[N,N′-(1,2-Diphenyl­ethane-1,2-di­yl)bis­(pyridine-2-carboxamidato)]nickel(II) diethyl ether hemisolvate

Yang, L.; Deng, D.-Y.; Li, M.; Zhou, X.-G.

doi:10.1107/S1600536808002882

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Page m439

doi:10.1107/S1600536808002882

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[N,N′-(1,2-Diphenylethane-1,2-diyl)bis(pyridine-2-carboxamidato)]nickel(II) diethyl ether hemisolvate

Li Yang,^a Dong-Yan Deng,^a Mei Li ^a and Xiang-Ge Zhou ^a ^*

^aInstitute of Homogeneous Catalysis, Department of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China
^*Correspondence e-mail: scuzhouxg@163.com

(Received 19 November 2007; accepted 25 January 2008; online 6 February 2008)

In the title compound, [Ni(C₂₆H₂₀N₄O₂)]·0.5C₄H₁₀O, the central metal ion is coordinated by four atoms of the tetradentate picolinamide ligand, forming a slightly distorted square-planar configuration, with an average Ni—N(pyridine) distance of 1.94 Å and an average Ni—N(amide) distance of 1.83 Å. The asymmetric unit contains one half-molecule of diethyl ether; this solvent molecule is disordered across a twofold rotation axis..

Related literature

For related literature, see: Barnes et al. (1981 ); Doukov et al. (2002 ); Fenton et al. (1991 ); Halcrow et al. (1994 ); Mulqi et al. (1981 ); Yang et al. (2007 ).

Experimental

Crystal data

[Ni(C₂₆H₂₀N₄O₂)]·0.5C₄H₁₀O
M_r = 516.23
Monoclinic, C 2
a = 21.838 (3) Å
b = 11.1675 (15) Å
c = 11.0443 (15) Å
β = 100.949 (3)°
V = 2644.5 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.77 mm⁻¹
T = 294 (2) K
0.38 × 0.14 × 0.06 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.879, T_max = 0.956
12577 measured reflections
6078 independent reflections
3405 reflections with I > 2σ(I)
R_int = 0.067

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.162
S = 1.01
6078 reflections
325 parameters
17 restraints
H-atom parameters constrained
Δρ_max = 0.82 e Å⁻³
Δρ_min = −0.43 e Å⁻³
Absolute structure: Flack (1983 ), 2840 Friedel pairs
Flack parameter: 0.03 (2)

Table 1
Selected bond lengths (Å)

Ni1—N3	1.8227 (13)
Ni1—N1	1.8349 (17)
Ni1—N2	1.9410 (17)
Ni1—N4	1.9527 (17)

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808002882/av2001sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808002882/av2001Isup2.hkl

checkCIF report

Comment top

Nickel exists in organism as a trace element and it often acts as component or secondary factor of enzyme (Doukov et al., 2002). In the latest two decades, the coordination chemistry of nickel has made a great progress (Halcrow et al., 1994). On the other hand, pyridine carboxamides, being a burgeoning class of multidentate ligands, are available easily from condensation reactions of pyridine carboxylic acid and amine. Continuing of our study in the synthesis and application of complexes containing picolinamide ligands in catalysis (Yang et al., 2007), herein is reported the crystal structure of Ni(II) with chiral pyridine carboxamide ligand, 1,2-bis(2-pyridinecarboxamido)-1,2-diphenylethane(s,s-bpdpeH₂).

Selected bond lengths and angles in the title compound are listed in Table 1. Figure 1 shows a perspective drawing of the molecule with atom labeling. In the title compound, there is one solvent ether molecules per two complex molecules. X-Ray crystallography revealed that the nickel ion coordinates with the four nitrogen atoms of picolinamide ligand with Ni–N bond distances ranging from 1.8227 (13) to 1.9527 (17) Å. The sum of the four N—Ni—N angles is 360.48°. The dihedral angle between the two pyridyl rings is less than 2°, the Ni(II) ion seems to form a slightly distorted square plane configuration. Furthermore, the Ni—N(amide) distances are shorter than the Ni—N(pyridine) distances, which is similar with the reported complex such as [Ni(bcph)](H₂bpch=1, 2-bis(2-pyridinecarboxamido)-1, 2- cyclohexane) with Ni—N(amide)=1.87 Å and Ni—N(pyridine)=1.94 Å (Mulqi et al., 1981).

Related literature top

For related literature, see: Barnes et al. (1981); Doukov et al. (2002); Fenton et al. (1991); Halcrow et al. (1994); Mulqi et al. (1981); Yang et al. (2007).

Experimental top

The ligand was prepared by a previously described method (Fenton et al., 1991). The title complex was obtained analogous to (Barnes et al., 1981). Single crystals suitable for X-ray analysis were obtained by slow diffusion of diethyl ether into a DMF solution of the complex. Selected IR data (KBr, cm^-1): 2980 (m), 1650 (amide I band, s), 1610(amide II band, s), 1470 (s), 1360 (s), 1120(s), 1020 (m), 870 (m). Analysis calculated for C₂₆H₂₀N₄NiO₂: C 65.17, H 4.21, N 11.69%; found: C 65.23, H 4.43, N 11.54%. MS (FAB): 479([Ni(bpdpe)]⁺).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 (Sheldrick, 2008).

Figures top

Fig. 1. 1 A view of [Ni(C₂₆H₂₀N₄O₂)].1/2(C₂H₅OC₂H₅), with displacement ellipsoids drawn at the 30% propability level.

[N,N'-(1,2-Diphenylethane-1,2-diyl)bis(pyridine-2-carboxamidato)]nickel(II) diethyl ether hemisolvate top

Crystal data top

[Ni(C₂₆H₂₀N₄O₂)]·0.5C₄H₁₀O	F(000) = 1076
M_r = 516.23	D_x = 1.297 Mg m⁻³
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
a = 21.838 (3) Å	Cell parameters from 4983 reflections
b = 11.1675 (15) Å	θ = 1–27.5°
c = 11.0443 (15) Å	µ = 0.77 mm⁻¹
β = 100.949 (3)°	T = 294 K
V = 2644.5 (6) Å³	Needle, green
Z = 4	0.38 × 0.14 × 0.06 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	6078 independent reflections
Radiation source: fine-focus sealed tube	3405 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.067
ϕ and ω scans	θ_max = 27.6°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −28→28
T_min = 0.879, T_max = 0.956	k = −14→14
12577 measured reflections	l = −14→13

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.058	H-atom parameters constrained
wR(F²) = 0.162	w = 1/[σ²(F_o²) + (0.067P)²] and P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.007
6078 reflections	Δρ_max = 0.82 e Å⁻³
325 parameters	Δρ_min = −0.43 e Å⁻³
17 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.03 (2)

Crystal data top

[Ni(C₂₆H₂₀N₄O₂)]·0.5C₄H₁₀O	V = 2644.5 (6) Å³
M_r = 516.23	Z = 4
Monoclinic, C2	Mo Kα radiation
a = 21.838 (3) Å	µ = 0.77 mm⁻¹
b = 11.1675 (15) Å	T = 294 K
c = 11.0443 (15) Å	0.38 × 0.14 × 0.06 mm
β = 100.949 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	6078 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3405 reflections with I > 2σ(I)
T_min = 0.879, T_max = 0.956	R_int = 0.067
12577 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	H-atom parameters constrained
wR(F²) = 0.162	Δρ_max = 0.82 e Å⁻³
S = 1.01	Δρ_min = −0.43 e Å⁻³
6078 reflections	Absolute structure: Flack (1983)
325 parameters	Absolute structure parameter: 0.03 (2)
17 restraints

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	Occ. (<1)
Ni1	0.685445 (11)	0.41062 (2)	0.575362 (19)	0.03992 (6)
O1	0.68109 (9)	0.75302 (12)	0.48680 (13)	0.0649 (6)
O2	0.71735 (10)	0.29814 (15)	0.91975 (14)	0.0807 (7)
N1	0.69128 (8)	0.57385 (15)	0.59271 (15)	0.0448 (6)
N2	0.67548 (8)	0.44546 (14)	0.40053 (15)	0.0463 (6)
N3	0.70417 (7)	0.41280 (19)	0.74336 (12)	0.0404 (4)
N4	0.67459 (9)	0.23904 (15)	0.59807 (15)	0.0472 (6)
C1	0.73171 (10)	0.52214 (17)	0.80298 (19)	0.0427 (6)
H1	0.7199	0.5305	0.8839	0.051*
C2	0.70105 (11)	0.62494 (17)	0.71610 (18)	0.0437 (7)
H2	0.7313	0.6904	0.7202	0.052*
C3	0.68186 (11)	0.64212 (19)	0.49332 (19)	0.0501 (7)
C4	0.67389 (11)	0.56614 (19)	0.37879 (19)	0.0455 (7)
C5	0.66656 (13)	0.6111 (2)	0.2626 (2)	0.0642 (9)
H5	0.6622	0.6933	0.2506	0.077*
C6	0.66545 (15)	0.5382 (2)	0.1635 (2)	0.0763 (10)
H6	0.6618	0.5691	0.0843	0.092*
C7	0.66992 (12)	0.4171 (3)	0.18509 (18)	0.0763 (8)
H7	0.6700	0.3642	0.1201	0.092*
C8	0.67431 (12)	0.37406 (18)	0.30362 (19)	0.0579 (8)
H8	0.6765	0.2917	0.3163	0.069*
C9	0.70290 (12)	0.3139 (2)	0.8047 (2)	0.0528 (8)
C10	0.68154 (12)	0.21015 (19)	0.7192 (2)	0.0480 (7)
C11	0.67415 (14)	0.0961 (2)	0.7604 (2)	0.0704 (9)
H11	0.6793	0.0798	0.8443	0.084*
C12	0.65897 (14)	0.0069 (2)	0.6752 (2)	0.0777 (10)
H12	0.6520	−0.0704	0.7008	0.093*
C13	0.65399 (16)	0.0315 (2)	0.5531 (3)	0.0847 (11)
H13	0.6464	−0.0294	0.4947	0.102*
C14	0.66052 (14)	0.1488 (2)	0.5177 (2)	0.0718 (10)
H14	0.6549	0.1660	0.4339	0.086*
C15	0.80143 (10)	0.52376 (17)	0.81812 (17)	0.0390 (6)
C16	0.83346 (10)	0.45226 (18)	0.74753 (19)	0.0507 (7)
H16	0.8115	0.4001	0.6894	0.061*
C17	0.89797 (11)	0.4584 (2)	0.7635 (2)	0.0614 (8)
H17	0.9189	0.4098	0.7163	0.074*
C18	0.93127 (12)	0.5359 (2)	0.8487 (2)	0.0700 (10)
H18	0.9745	0.5400	0.8592	0.084*
C19	0.90017 (11)	0.6058 (2)	0.9169 (2)	0.0680 (9)
H19	0.9224	0.6580	0.9747	0.082*
C20	0.83604 (11)	0.60110 (19)	0.9019 (2)	0.0579 (8)
H20	0.8157	0.6509	0.9492	0.070*
C21	0.64296 (11)	0.67357 (18)	0.7536 (2)	0.0484 (7)
C22	0.64900 (12)	0.7353 (2)	0.86491 (19)	0.0651 (9)
H22	0.6886	0.7457	0.9124	0.078*
C23	0.59732 (12)	0.7826 (3)	0.9082 (2)	0.0837 (10)
H23	0.6023	0.8222	0.9835	0.100*
C24	0.54060 (14)	0.7686 (3)	0.8374 (2)	0.1052 (12)
H24	0.5060	0.7988	0.8649	0.126*
C25	0.53215 (14)	0.7107 (3)	0.7252 (3)	0.1189 (15)
H25	0.4926	0.7042	0.6766	0.143*
C26	0.58374 (12)	0.6620 (3)	0.6855 (3)	0.0820 (11)
H26	0.5779	0.6207	0.6110	0.098*
C28	0.5081 (3)	0.3730 (6)	0.7884 (4)	0.364 (3)
H28A	0.5451	0.3351	0.7625	0.545*
H28B	0.4932	0.4332	0.7310	0.545*
H28C	0.4779	0.3102	0.7870	0.545*
C27	0.5289 (3)	0.4225 (3)	0.9168 (4)	0.251 (3)
H27A	0.5430	0.3517	0.9655	0.301*
H27B	0.5654	0.4671	0.9113	0.301*
O3	0.5000	0.4919 (6)	1.0000	0.219 (6)	0.50
O3'	0.5000	0.3518 (7)	1.0000	0.380 (6)	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.06559 (13)	0.02383 (9)	0.03095 (10)	0.00039 (17)	0.01070 (9)	0.00210 (15)
O1	0.1240 (13)	0.0250 (8)	0.0457 (9)	0.0052 (9)	0.0160 (9)	0.0088 (7)
O2	0.1566 (16)	0.0453 (9)	0.0339 (8)	−0.0197 (11)	0.0019 (10)	0.0124 (8)
N1	0.0760 (12)	0.0243 (8)	0.0353 (9)	0.0007 (9)	0.0135 (9)	0.0004 (7)
N2	0.0710 (11)	0.0316 (10)	0.0374 (9)	0.0087 (8)	0.0134 (8)	0.0049 (7)
N3	0.0659 (9)	0.0242 (6)	0.0322 (7)	0.0023 (13)	0.0121 (6)	0.0067 (11)
N4	0.0769 (13)	0.0262 (9)	0.0393 (9)	−0.0040 (9)	0.0135 (9)	−0.0007 (8)
C1	0.0740 (14)	0.0244 (9)	0.0277 (10)	−0.0028 (10)	0.0046 (10)	−0.0016 (8)
C2	0.0765 (14)	0.0247 (10)	0.0303 (10)	−0.0015 (10)	0.0116 (10)	−0.0004 (9)
C3	0.0876 (16)	0.0279 (10)	0.0345 (11)	−0.0060 (11)	0.0106 (11)	0.0093 (9)
C4	0.0681 (14)	0.0292 (10)	0.0391 (11)	0.0008 (10)	0.0100 (11)	0.0042 (9)
C5	0.1020 (19)	0.0462 (14)	0.0438 (13)	0.0003 (14)	0.0126 (13)	0.0142 (11)
C6	0.155 (2)	0.0498 (14)	0.0255 (11)	−0.0059 (16)	0.0196 (14)	0.0090 (11)
C7	0.1395 (19)	0.0557 (13)	0.0351 (10)	0.003 (2)	0.0202 (12)	−0.0076 (17)
C8	0.1057 (18)	0.0313 (12)	0.0371 (11)	0.0017 (11)	0.0143 (12)	−0.0059 (9)
C9	0.0805 (16)	0.0366 (11)	0.0392 (12)	−0.0092 (12)	0.0064 (12)	0.0019 (11)
C10	0.0764 (15)	0.0277 (10)	0.0385 (11)	−0.0036 (11)	0.0071 (11)	0.0032 (10)
C11	0.126 (2)	0.0362 (12)	0.0477 (14)	−0.0156 (14)	0.0135 (15)	0.0124 (11)
C12	0.138 (2)	0.0313 (12)	0.0627 (16)	−0.0212 (15)	0.0159 (16)	0.0045 (12)
C13	0.164 (3)	0.0283 (12)	0.0686 (17)	−0.0175 (16)	0.0389 (17)	−0.0009 (12)
C14	0.130 (2)	0.0402 (13)	0.0430 (14)	−0.0073 (16)	0.0109 (15)	−0.0037 (12)
C15	0.0572 (13)	0.0281 (10)	0.0299 (10)	0.0041 (10)	0.0038 (10)	0.0008 (9)
C16	0.0786 (15)	0.0347 (11)	0.0374 (11)	0.0045 (11)	0.0078 (11)	−0.0029 (9)
C17	0.0718 (16)	0.0565 (15)	0.0536 (14)	0.0109 (12)	0.0061 (13)	−0.0005 (12)
C18	0.0674 (16)	0.0630 (16)	0.0749 (18)	0.0069 (15)	0.0016 (15)	0.0033 (15)
C19	0.0727 (17)	0.0471 (14)	0.0736 (18)	−0.0122 (13)	−0.0130 (15)	−0.0155 (13)
C20	0.0940 (18)	0.0326 (11)	0.0450 (12)	−0.0006 (13)	0.0075 (13)	−0.0119 (10)
C21	0.0674 (14)	0.0300 (11)	0.0467 (12)	0.0131 (11)	0.0082 (11)	−0.0017 (10)
C22	0.1067 (19)	0.0447 (14)	0.0461 (13)	0.0150 (14)	0.0198 (13)	−0.0005 (12)
C23	0.134 (2)	0.0629 (16)	0.0640 (15)	0.0292 (17)	0.0439 (14)	0.0049 (14)
C24	0.111 (2)	0.134 (3)	0.0792 (18)	0.0655 (19)	0.0387 (15)	0.0075 (19)
C25	0.081 (2)	0.149 (3)	0.126 (3)	0.053 (2)	0.017 (2)	−0.004 (3)
C26	0.0860 (19)	0.091 (2)	0.0678 (18)	0.0157 (17)	0.0106 (16)	−0.0138 (16)
C28	0.301 (5)	0.388 (7)	0.344 (7)	−0.243 (5)	−0.087 (6)	0.170 (6)
C27	0.293 (6)	0.249 (7)	0.188 (5)	0.067 (7)	−0.011 (5)	−0.015 (6)
O3	0.167 (8)	0.173 (9)	0.306 (14)	0.000	0.022 (9)	0.000
O3'	0.382 (16)	0.400 (3)	0.398 (3)	−0.26 (2)	0.176 (13)	−0.13 (4)

Geometric parameters (Å, º) top

Ni1—N3	1.8227 (13)	C13—C14	1.383 (4)
Ni1—N1	1.8349 (17)	C13—H13	0.9300
Ni1—N2	1.9410 (17)	C14—H14	0.9300
Ni1—N4	1.9527 (17)	C15—C20	1.381 (3)
O1—C3	1.241 (3)	C15—C16	1.394 (3)
O2—C9	1.263 (3)	C16—C17	1.388 (3)
N1—C3	1.320 (3)	C16—H16	0.9300
N1—C2	1.455 (3)	C17—C18	1.380 (3)
N2—C8	1.331 (3)	C17—H17	0.9300
N2—C4	1.368 (3)	C18—C19	1.354 (4)
N3—C9	1.298 (3)	C18—H18	0.9300
N3—C1	1.461 (3)	C19—C20	1.380 (3)
N4—C14	1.339 (3)	C19—H19	0.9300
N4—C10	1.357 (3)	C20—H20	0.9300
C1—C15	1.500 (3)	C21—C26	1.373 (3)
C1—C2	1.563 (3)	C21—C22	1.393 (3)
C1—H1	0.9800	C22—C23	1.409 (4)
C2—C21	1.509 (3)	C22—H22	0.9300
C2—H2	0.9800	C23—C24	1.342 (4)
C3—C4	1.506 (3)	C23—H23	0.9300
C4—C5	1.359 (3)	C24—C25	1.378 (4)
C5—C6	1.361 (3)	C24—H24	0.9300
C5—H5	0.9300	C25—C26	1.395 (4)
C6—C7	1.373 (4)	C25—H25	0.9300
C6—H6	0.9300	C26—H26	0.9300
C7—C8	1.381 (3)	C28—C27	1.510 (6)
C7—H7	0.9300	C28—H28A	1.0002
C8—H8	0.9300	C28—H28B	0.9388
C9—C10	1.511 (3)	C28—H28C	0.9612
C10—C11	1.372 (3)	C27—O3	1.436 (6)
C11—C12	1.366 (3)	C27—H27A	0.9730
C11—H11	0.9300	C27—H27B	0.9523
C12—C13	1.360 (4)	O3—C27ⁱ	1.436 (6)
C12—H12	0.9300

N3—Ni1—N1	83.26 (8)	C13—C12—H12	120.0
N3—Ni1—N2	166.18 (8)	C11—C12—H12	120.0
N1—Ni1—N2	84.10 (7)	C12—C13—C14	118.6 (2)
N3—Ni1—N4	83.78 (8)	C12—C13—H13	120.7
N1—Ni1—N4	165.74 (8)	C14—C13—H13	120.7
N2—Ni1—N4	109.33 (7)	N4—C14—C13	123.3 (2)
C3—N1—C2	121.62 (17)	N4—C14—H14	118.4
C3—N1—Ni1	119.35 (14)	C13—C14—H14	118.4
C2—N1—Ni1	118.83 (13)	C20—C15—C16	117.7 (2)
C8—N2—C4	116.94 (17)	C20—C15—C1	119.79 (19)
C8—N2—Ni1	131.39 (14)	C16—C15—C1	122.51 (17)
C4—N2—Ni1	111.49 (13)	C17—C16—C15	120.40 (19)
C9—N3—C1	121.56 (15)	C17—C16—H16	119.8
C9—N3—Ni1	119.77 (16)	C15—C16—H16	119.8
C1—N3—Ni1	117.61 (14)	C18—C17—C16	120.5 (2)
C14—N4—C10	116.33 (19)	C18—C17—H17	119.7
C14—N4—Ni1	132.16 (16)	C16—C17—H17	119.7
C10—N4—Ni1	111.49 (13)	C19—C18—C17	119.1 (2)
N3—C1—C15	112.49 (17)	C19—C18—H18	120.4
N3—C1—C2	104.21 (15)	C17—C18—H18	120.4
C15—C1—C2	111.53 (18)	C18—C19—C20	121.1 (2)
N3—C1—H1	109.5	C18—C19—H19	119.5
C15—C1—H1	109.5	C20—C19—H19	119.5
C2—C1—H1	109.5	C19—C20—C15	121.2 (2)
N1—C2—C21	114.66 (17)	C19—C20—H20	119.4
N1—C2—C1	104.85 (16)	C15—C20—H20	119.4
C21—C2—C1	112.35 (18)	C26—C21—C22	116.8 (2)
N1—C2—H2	108.2	C26—C21—C2	124.7 (2)
C21—C2—H2	108.2	C22—C21—C2	118.5 (2)
C1—C2—H2	108.2	C21—C22—C23	122.5 (2)
O1—C3—N1	128.5 (2)	C21—C22—H22	118.8
O1—C3—C4	121.05 (19)	C23—C22—H22	118.8
N1—C3—C4	110.37 (18)	C24—C23—C22	118.0 (3)
C5—C4—N2	121.6 (2)	C24—C23—H23	121.0
C5—C4—C3	124.0 (2)	C22—C23—H23	121.0
N2—C4—C3	114.37 (18)	C23—C24—C25	121.9 (3)
C4—C5—C6	121.3 (2)	C23—C24—H24	119.0
C4—C5—H5	119.4	C25—C24—H24	119.0
C6—C5—H5	119.4	C24—C25—C26	119.2 (3)
C5—C6—C7	117.4 (2)	C24—C25—H25	120.4
C5—C6—H6	121.3	C26—C25—H25	120.4
C7—C6—H6	121.3	C21—C26—C25	121.6 (3)
C6—C7—C8	119.8 (2)	C21—C26—H26	119.2
C6—C7—H7	120.1	C25—C26—H26	119.2
C8—C7—H7	120.1	C27—C28—H28A	108.0
N2—C8—C7	122.8 (2)	C27—C28—H28B	112.0
N2—C8—H8	118.6	H28A—C28—H28B	107.9
C7—C8—H8	118.6	C27—C28—H28C	111.4
O2—C9—N3	128.2 (2)	H28A—C28—H28C	106.1
O2—C9—C10	120.6 (2)	H28B—C28—H28C	111.2
N3—C9—C10	111.19 (18)	O3—C27—C28	135.1 (5)
N4—C10—C11	123.3 (2)	O3—C27—H27A	102.5
N4—C10—C9	113.38 (19)	C28—C27—H27A	103.2
C11—C10—C9	123.2 (2)	O3—C27—H27B	103.6
C12—C11—C10	118.5 (2)	C28—C27—H27B	103.7
C12—C11—H11	120.7	H27A—C27—H27B	106.1
C10—C11—H11	120.7	C27—O3—C27ⁱ	114.7 (6)
C13—C12—C11	119.9 (2)

N3—Ni1—N1—C3	−179.99 (19)	C4—C5—C6—C7	2.1 (4)
N2—Ni1—N1—C3	5.60 (18)	C5—C6—C7—C8	1.0 (4)
N4—Ni1—N1—C3	−155.1 (3)	C4—N2—C8—C7	−1.8 (4)
N3—Ni1—N1—C2	−5.08 (16)	Ni1—N2—C8—C7	−176.47 (19)
N2—Ni1—N1—C2	−179.49 (17)	C6—C7—C8—N2	−1.2 (4)
N4—Ni1—N1—C2	19.8 (4)	C1—N3—C9—O2	8.3 (4)
N3—Ni1—N2—C8	147.3 (3)	Ni1—N3—C9—O2	176.2 (2)
N1—Ni1—N2—C8	171.2 (2)	C1—N3—C9—C10	−171.00 (19)
N4—Ni1—N2—C8	−13.7 (2)	Ni1—N3—C9—C10	−3.1 (3)
N3—Ni1—N2—C4	−27.6 (4)	C14—N4—C10—C11	−0.8 (4)
N1—Ni1—N2—C4	−3.66 (15)	Ni1—N4—C10—C11	177.7 (2)
N4—Ni1—N2—C4	171.40 (15)	C14—N4—C10—C9	174.9 (2)
N1—Ni1—N3—C9	173.64 (18)	Ni1—N4—C10—C9	−6.6 (3)
N2—Ni1—N3—C9	−162.4 (3)	O2—C9—C10—N4	−173.0 (2)
N4—Ni1—N3—C9	−0.38 (18)	N3—C9—C10—N4	6.4 (3)
N1—Ni1—N3—C1	−17.93 (15)	O2—C9—C10—C11	2.8 (4)
N2—Ni1—N3—C1	6.0 (4)	N3—C9—C10—C11	−177.9 (2)
N4—Ni1—N3—C1	168.04 (15)	N4—C10—C11—C12	−0.1 (4)
N3—Ni1—N4—C14	−177.7 (3)	C9—C10—C11—C12	−175.3 (3)
N1—Ni1—N4—C14	157.5 (3)	C10—C11—C12—C13	2.6 (5)
N2—Ni1—N4—C14	−2.2 (3)	C11—C12—C13—C14	−4.2 (5)
N3—Ni1—N4—C10	4.10 (16)	C10—N4—C14—C13	−0.9 (4)
N1—Ni1—N4—C10	−20.7 (4)	Ni1—N4—C14—C13	−179.0 (2)
N2—Ni1—N4—C10	179.62 (16)	C12—C13—C14—N4	3.4 (5)
C9—N3—C1—C15	80.8 (2)	N3—C1—C15—C20	−161.45 (18)
Ni1—N3—C1—C15	−87.42 (17)	C2—C1—C15—C20	81.9 (2)
C9—N3—C1—C2	−158.3 (2)	N3—C1—C15—C16	20.7 (3)
Ni1—N3—C1—C2	33.5 (2)	C2—C1—C15—C16	−96.0 (2)
C3—N1—C2—C21	74.7 (3)	C20—C15—C16—C17	1.0 (3)
Ni1—N1—C2—C21	−100.11 (18)	C1—C15—C16—C17	178.9 (2)
C3—N1—C2—C1	−161.6 (2)	C15—C16—C17—C18	−0.5 (3)
Ni1—N1—C2—C1	23.6 (2)	C16—C17—C18—C19	0.1 (4)
N3—C1—C2—N1	−32.9 (2)	C17—C18—C19—C20	−0.3 (4)
C15—C1—C2—N1	88.7 (2)	C18—C19—C20—C15	0.8 (4)
N3—C1—C2—C21	92.29 (19)	C16—C15—C20—C19	−1.2 (3)
C15—C1—C2—C21	−146.11 (17)	C1—C15—C20—C19	−179.2 (2)
C2—N1—C3—O1	1.8 (4)	N1—C2—C21—C26	6.3 (3)
Ni1—N1—C3—O1	176.5 (2)	C1—C2—C21—C26	−113.2 (3)
C2—N1—C3—C4	179.4 (2)	N1—C2—C21—C22	−173.36 (19)
Ni1—N1—C3—C4	−5.8 (3)	C1—C2—C21—C22	67.0 (2)
C8—N2—C4—C5	5.0 (3)	C26—C21—C22—C23	1.1 (4)
Ni1—N2—C4—C5	−179.3 (2)	C2—C21—C22—C23	−179.2 (2)
C8—N2—C4—C3	−174.1 (2)	C21—C22—C23—C24	−1.2 (4)
Ni1—N2—C4—C3	1.6 (2)	C22—C23—C24—C25	−0.4 (5)
O1—C3—C4—C5	1.2 (4)	C23—C24—C25—C26	2.0 (6)
N1—C3—C4—C5	−176.6 (2)	C22—C21—C26—C25	0.6 (4)
O1—C3—C4—N2	−179.7 (2)	C2—C21—C26—C25	−179.2 (3)
N1—C3—C4—N2	2.4 (3)	C24—C25—C26—C21	−2.1 (5)
N2—C4—C5—C6	−5.3 (4)	C28—C27—O3—C27ⁱ	91.6 (7)
C3—C4—C5—C6	173.7 (3)

Symmetry code: (i) −x+1, y, −z+2.

Experimental details

Crystal data
Chemical formula	[Ni(C₂₆H₂₀N₄O₂)]·0.5C₄H₁₀O
M_r	516.23
Crystal system, space group	Monoclinic, C2
Temperature (K)	294
a, b, c (Å)	21.838 (3), 11.1675 (15), 11.0443 (15)
β (°)	100.949 (3)
V (Å³)	2644.5 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.77
Crystal size (mm)	0.38 × 0.14 × 0.06

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.879, 0.956
No. of measured, independent and observed [I > 2σ(I)] reflections	12577, 6078, 3405
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.652

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.162, 1.01
No. of reflections	6078
No. of parameters	325
No. of restraints	17
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.82, −0.43
Absolute structure	Flack (1983)
Absolute structure parameter	0.03 (2)

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Ni1—N3	1.8227 (13)	Ni1—N2	1.9410 (17)
Ni1—N1	1.8349 (17)	Ni1—N4	1.9527 (17)

Acknowledgements

This project was sponsored by the NSFC (grant Nos. 20672075, 20771076) and the Student Innovation Foundation of Sichuan University.

References

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