Poly[[μ-1,4-bis­(imidazol-1-ylmeth­yl)benzene]bis­(μ4-cyclo­hexane-1,4-dicarboxyl­ato)dinickel(II)]

Li, B.-B.; Fang, G.-X.; Ji, X.-N.; Xiao, B.; Tiekink, E.R.T.

doi:10.1107/S1600536809029249

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page m1012

doi:10.1107/S1600536809029249

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Poly[[μ-1,4-bis(imidazol-1-ylmethyl)benzene]bis(μ₄-cyclohexane-1,4-dicarboxylato)dinickel(II)]

Bing-Bing Li,^a,^b ^* Gai-Xia Fang,^a Xiao-Na Ji,^a Bo Xiao ^b and Edward R. T. Tiekink ^c

^aDepartment of Bioengineering, Henan University of Urban Construction, Pingdingshan 467000, People's Republic of China, ^bSchool of Environmental Science and Engineering, Huazhong University of Science and Technology, Wuhan 430074, People's Republic of China, and ^cDepartment of Chemistry, Universidade Federal de São Carlos, 13565-905 São Carlos, SP, Brazil
^*Correspondence e-mail: libingbinghncj@yahoo.com.cn

(Received 21 July 2009; accepted 23 July 2009; online 31 July 2009)

The structure of the polymeric title compound, [Ni₂(C₈H₁₀O₄)₂(C₁₄H₁₄N₄)]_n, features a five-coordinate Ni^II centre defined by four carboxylate O atoms from two different cyclohexane-1,4-dicarboxylate (chdc) ligands and an N atom from one end of a 1,4-bis(imidazol-1-ylmethyl)benzene (1,4-bix) molecule. The NO₄ coordination geometry is distorted square-pyramidal with the N atom in the apical position. Each end of the chdc ligand links pairs of Ni^II atoms into a paddle-wheel assembly, i.e. Ni₂(O₂CR′)₄. These are connected into rows owing to the bridging nature of the chdc ligands, and the rows are connected into a two-dimensional grid via the 1,4-bix ligands. The 1,4-bix ligand, which is disposed about a centre of inversion, is disorderd. Two positions of equal occupancy were discerned for the –H₂C(C₆H₄)CH₂– residue.

Related literature

For background to coordination polymers, see: Batten & Robson (1998 ); Kim & Jung (2002 ); Yang et al. (2008 ). For a related Ni(II) structure, see: Lee et al. (2003 ).

Experimental

Crystal data

[Ni₂(C₈H₁₀O₄)₂(C₁₄H₁₄N₄)]
M_r = 696.03
Triclinic, $[P \overline 1]$
a = 8.4966 (6) Å
b = 8.8076 (6) Å
c = 10.7327 (8) Å
α = 93.567 (6)°
β = 100.608 (6)°
γ = 105.807 (6)°
V = 754.22 (9) Å³
Z = 1
Mo Kα radiation
μ = 1.31 mm⁻¹
T = 293 K
0.31 × 0.22 × 0.18 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.557, T_max = 0.791
6115 measured reflections
2640 independent reflections
2287 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.139
S = 1.11
2640 reflections
224 parameters
36 restraints
H-atom parameters constrained
Δρ_max = 1.30 e Å⁻³
Δρ_min = −1.25 e Å⁻³

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1999 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809029249/ng2618sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809029249/ng2618Isup2.hkl

checkCIF report

Comment top

Metal–organic coordination polymers continue to attract considerable interest owing to their well documented and varied applications (Yang et al., 2008). These coordination polymers can be specially designed by the careful selection of metal cations with preferred coordination geometries, the nature of the anions, the structure of the connecting ligands, and the reaction conditions (Kim & Jung, 2002). The selection of ligand is extremely important because changing their geometries can control the topologies of the resulting coordination frameworks. While the rigid rod-like spacer, 4,4'-bipyridine, is well known in the construction of metal-organic polymers, flexible N-donor ligands such as 1,4-bis(imidazole-1-ylmethyl)benzene (1,4-bix) have not been so well explored. In this work, 1,4-bix assembles with nickel cyclohexane-1,4-dicarboxylate (chdc) to furnish [Ni(chdc)(1,4-bix)_0.5], (I), which exists as a 2-D array.

The asymmetric unit of (I) comprises a Ni atom, a chdc dianion, and half a 1-4-bix molecule which is disposed about a centre of inversion (Fig. 1). Each end of the chdc ligand bridges a pair of Ni atoms to result in the formation of a paddle-wheel assembly, i.e. Ni₂(O₂CR')₄. These are linked into rows which, in turn, are linked via the bridging 1,4-bix ligands into a 2-D array in the bc plane (Fig. 2). The layers are stacked in an ···ABC··· fashion (Fig. 3). The coordination geometry is based on a NO₄ donor set that defines a square pyramid with the N donor atom in the apical position. If the second Ni atom in the paddle-wheel assembly is considered as occupying a coordination site, the Ni···Niⁱ distance is 2.6529 (10) Å, the coordination geometry would be distorted octahedral; symmetry operation i: 2-x, 1-y, 1-z.

Related literature top

For background to coordination polymers, see: Batten & Robson (1998); Kim & Jung (2002); Yang et al. (2008). For a related Ni(II) structure, see: Lee et al. (2003).

Experimental top

Nickel chloride hexahydrate (0.118 g, 0.5 mmol), H₂chdc (0.135 g, 0.5 mmol) and 1,4-bix (0.093 g, 0.5 mmol) were placed in water (12 ml), and triethylamine was added until the pH value of the solution was 5.7. The solution was heated in a 23-ml Teflon-lined stainless-steel autoclave at 440 K for 5 days. The autoclave was allowed to cool to room temperature over several hours. Green blocks were isolated in about 61% yield.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit in the polymeric structure of (I), showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Only one component of the disordered -CH₂(C₆H₄)CH₂- residue is shown.
	Fig. 2. View of the 2-D array in (I). H atoms have been omitted for clarity.
	Fig. 3. View of the stacking of the layers in the crystal structure of (I). H atoms have been omitted for clarity.

Poly[[µ-1,4-bis(imidazol-1-ylmethyl)benzene]bis(µ₄-cyclohexane-1,4- dicarboxylato)dinickel(II)] top

Crystal data top

[Ni₂(C₈H₁₀O₄)₂(C₁₄H₁₄N₄)]	Z = 1
M_r = 696.03	F(000) = 362
Triclinic, P1	D_x = 1.532 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4966 (6) Å	Cell parameters from 3051 reflections
b = 8.8076 (6) Å	θ = 3.0–26.4°
c = 10.7327 (8) Å	µ = 1.31 mm⁻¹
α = 93.567 (6)°	T = 293 K
β = 100.608 (6)°	Block, green
γ = 105.807 (6)°	0.31 × 0.22 × 0.18 mm
V = 754.22 (9) Å³

Data collection top

Bruker SMART APEX diffractometer	2640 independent reflections
Radiation source: fine-focus sealed tube	2287 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 25.0°, θ_min = 4.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.557, T_max = 0.791	k = −10→10
6115 measured reflections	l = −12→12

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.139	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0653P)² + 2.0659P] where P = (F_o² + 2F_c²)/3
2640 reflections	(Δ/σ)_max < 0.001
224 parameters	Δρ_max = 1.30 e Å⁻³
36 restraints	Δρ_min = −1.25 e Å⁻³

Crystal data top

[Ni₂(C₈H₁₀O₄)₂(C₁₄H₁₄N₄)]	γ = 105.807 (6)°
M_r = 696.03	V = 754.22 (9) Å³
Triclinic, P1	Z = 1
a = 8.4966 (6) Å	Mo Kα radiation
b = 8.8076 (6) Å	µ = 1.31 mm⁻¹
c = 10.7327 (8) Å	T = 293 K
α = 93.567 (6)°	0.31 × 0.22 × 0.18 mm
β = 100.608 (6)°

Data collection top

Bruker SMART APEX diffractometer	2640 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2287 reflections with I > 2σ(I)
T_min = 0.557, T_max = 0.791	R_int = 0.025
6115 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	36 restraints
wR(F²) = 0.139	H-atom parameters constrained
S = 1.11	Δρ_max = 1.30 e Å⁻³
2640 reflections	Δρ_min = −1.25 e Å⁻³
224 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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)
Ni	1.02456 (6)	0.46763 (6)	0.61988 (5)	0.0239 (2)
O1	0.9631 (4)	0.6690 (4)	0.6585 (3)	0.0338 (7)
O2	0.9113 (4)	0.7154 (4)	0.4545 (3)	0.0335 (7)
O3	0.2691 (4)	0.5884 (4)	0.6790 (3)	0.0397 (8)
O4	0.2180 (4)	0.6331 (4)	0.4772 (3)	0.0418 (8)
N1	0.9779 (5)	0.3729 (5)	0.7773 (4)	0.0437 (8)
C1	0.9120 (5)	0.7449 (5)	0.5710 (4)	0.0264 (9)
C2	0.8505 (5)	0.8851 (5)	0.6088 (4)	0.0297 (10)
H2	0.9473	0.9801	0.6264	0.036*
C3	0.7810 (5)	0.8673 (6)	0.7302 (4)	0.0358 (11)
H3A	0.8616	0.8425	0.7962	0.043*
H3B	0.7655	0.9675	0.7597	0.043*
C4	0.6153 (5)	0.7376 (6)	0.7096 (4)	0.0323 (10)
H4A	0.5740	0.7329	0.7882	0.039*
H4B	0.6319	0.6356	0.6870	0.039*
C5	0.4869 (5)	0.7705 (5)	0.6037 (4)	0.0245 (9)
H5	0.4763	0.8750	0.6305	0.029*
C6	0.5532 (5)	0.7863 (6)	0.4803 (4)	0.0298 (10)
H6A	0.5667	0.6854	0.4501	0.036*
H6B	0.4726	0.8126	0.4152	0.036*
C7	0.7204 (5)	0.9147 (6)	0.5016 (5)	0.0340 (11)
H7A	0.7040	1.0172	0.5226	0.041*
H7B	0.7620	0.9179	0.4231	0.041*
C8	0.3134 (5)	0.6545 (5)	0.5852 (4)	0.0287 (10)
C9	1.0595 (8)	0.2825 (7)	0.8462 (5)	0.0573 (9)
H9	1.1499	0.2520	0.8274	0.069*
C10	0.9880 (8)	0.2448 (7)	0.9457 (6)	0.0573 (9)
H10	1.0191	0.1824	1.0070	0.069*
C11	0.8601 (8)	0.3888 (7)	0.8366 (5)	0.0573 (9)
H11	0.7842	0.4449	0.8098	0.069*
N2	0.8646 (6)	0.3123 (5)	0.9419 (4)	0.0437 (8)	0.50
C12	0.782 (2)	0.287 (2)	1.0446 (17)	0.047 (4)	0.50
H12A	0.7309	0.3719	1.0558	0.057*	0.50
H12B	0.8638	0.2931	1.1222	0.057*	0.50
C13	0.645 (2)	0.125 (2)	1.025 (2)	0.037 (4)	0.50
C14	0.653 (4)	0.031 (4)	1.109 (3)	0.063 (7)	0.50
H14	0.7448	0.0329	1.1717	0.075*	0.50
C15	0.520 (3)	0.084 (3)	0.916 (2)	0.050 (5)	0.50
H15	0.5460	0.1367	0.8469	0.060*	0.50
N2'	0.8646 (6)	0.3123 (5)	0.9419 (4)	0.0437 (8)	0.50
C12'	0.716 (2)	0.324 (2)	1.0150 (16)	0.059 (5)	0.50
H12C	0.7636	0.3649	1.1041	0.071*	0.50
H12D	0.6598	0.3975	0.9768	0.071*	0.50
C13'	0.594 (3)	0.164 (2)	1.005 (2)	0.045 (5)	0.50
C14'	0.606 (3)	0.063 (4)	1.104 (3)	0.057 (8)	0.50
H14'	0.6670	0.1156	1.1832	0.068*	0.50
C15'	0.464 (3)	0.114 (3)	0.898 (3)	0.055 (5)	0.50
H15'	0.4271	0.1766	0.8397	0.066*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni	0.0223 (3)	0.0278 (3)	0.0238 (3)	0.0071 (2)	0.0085 (2)	0.0080 (2)
O1	0.0353 (17)	0.0345 (18)	0.0354 (17)	0.0157 (14)	0.0079 (14)	0.0050 (14)
O2	0.0375 (18)	0.0329 (18)	0.0368 (18)	0.0149 (14)	0.0161 (14)	0.0087 (14)
O3	0.0254 (16)	0.043 (2)	0.049 (2)	0.0002 (14)	0.0171 (15)	0.0070 (16)
O4	0.0239 (16)	0.044 (2)	0.049 (2)	0.0069 (15)	−0.0055 (15)	−0.0014 (16)
N1	0.0501 (18)	0.0403 (17)	0.0287 (15)	−0.0138 (14)	0.0191 (13)	0.0039 (13)
C1	0.0152 (18)	0.024 (2)	0.039 (3)	0.0019 (16)	0.0096 (17)	0.0062 (19)
C2	0.0181 (19)	0.022 (2)	0.047 (3)	0.0016 (17)	0.0077 (18)	0.0006 (19)
C3	0.024 (2)	0.046 (3)	0.033 (2)	0.010 (2)	−0.0002 (18)	−0.010 (2)
C4	0.024 (2)	0.049 (3)	0.026 (2)	0.012 (2)	0.0081 (18)	0.010 (2)
C5	0.0177 (19)	0.026 (2)	0.031 (2)	0.0065 (17)	0.0069 (17)	0.0043 (17)
C6	0.024 (2)	0.038 (3)	0.030 (2)	0.0124 (19)	0.0068 (17)	0.0096 (19)
C7	0.028 (2)	0.034 (3)	0.050 (3)	0.014 (2)	0.021 (2)	0.017 (2)
C8	0.020 (2)	0.028 (2)	0.041 (3)	0.0090 (18)	0.0101 (19)	0.0035 (19)
C9	0.065 (2)	0.050 (2)	0.0432 (18)	−0.0045 (16)	0.0031 (16)	0.0189 (15)
C10	0.065 (2)	0.050 (2)	0.0432 (18)	−0.0045 (16)	0.0031 (16)	0.0189 (15)
C11	0.065 (2)	0.050 (2)	0.0432 (18)	−0.0045 (16)	0.0031 (16)	0.0189 (15)
N2	0.0501 (18)	0.0403 (17)	0.0287 (15)	−0.0138 (14)	0.0191 (13)	0.0039 (13)
C12	0.048 (10)	0.042 (8)	0.041 (8)	−0.010 (6)	0.020 (7)	0.003 (6)
C13	0.041 (9)	0.033 (10)	0.036 (8)	0.002 (6)	0.021 (7)	−0.006 (6)
C14	0.058 (15)	0.064 (14)	0.065 (11)	−0.004 (10)	0.041 (10)	0.009 (10)
C15	0.057 (14)	0.056 (11)	0.039 (9)	0.008 (9)	0.022 (10)	0.013 (8)
N2'	0.0501 (18)	0.0403 (17)	0.0287 (15)	−0.0138 (14)	0.0191 (13)	0.0039 (13)
C12'	0.070 (13)	0.054 (11)	0.040 (10)	−0.020 (8)	0.044 (9)	−0.016 (7)
C13'	0.064 (13)	0.031 (9)	0.039 (9)	−0.007 (7)	0.042 (10)	−0.001 (7)
C14'	0.050 (13)	0.071 (15)	0.035 (9)	−0.013 (10)	0.030 (9)	−0.026 (9)
C15'	0.047 (12)	0.058 (13)	0.056 (12)	0.001 (8)	0.022 (10)	0.010 (8)

Geometric parameters (Å, º) top

Ni—N1	1.987 (4)	C7—H7A	0.9700
Ni—O2ⁱ	2.003 (3)	C7—H7B	0.9700
Ni—O3ⁱⁱ	2.019 (3)	C9—C10	1.339 (8)
Ni—O1	2.021 (3)	C9—H9	0.9300
Ni—O4ⁱⁱⁱ	2.054 (3)	C10—N2	1.334 (8)
Ni—Niⁱ	2.6529 (10)	C10—N2'	1.334 (8)
O1—C1	1.266 (5)	C10—H10	0.9300
O2—C1	1.260 (5)	C11—N2	1.352 (7)
O2—Niⁱ	2.003 (3)	C11—N2'	1.352 (7)
O3—C8	1.260 (6)	C11—H11	0.9300
O3—Ni^iv	2.019 (3)	N2—C12	1.409 (18)
O4—C8	1.256 (6)	C12—C13	1.55 (3)
O4—Niⁱⁱⁱ	2.054 (3)	C12—H12A	0.9700
N1—C11	1.314 (8)	C12—H12B	0.9700
N1—C9	1.360 (8)	C13—C14	1.27 (5)
C1—C2	1.526 (6)	C13—C15	1.38 (3)
C2—C3	1.526 (6)	C14—C15^v	1.50 (4)
C2—C7	1.530 (6)	C14—H14	0.9300
C2—H2	0.9800	C15—C14^v	1.50 (4)
C3—C4	1.521 (6)	C15—H15	0.9300
C3—H3A	0.9700	N2'—C12'	1.626 (16)
C3—H3B	0.9700	C12'—C13'	1.49 (3)
C4—C5	1.524 (6)	C12'—H12C	0.9700
C4—H4A	0.9700	C12'—H12D	0.9700
C4—H4B	0.9700	C13'—C15'	1.39 (4)
C5—C8	1.517 (6)	C13'—C14'	1.43 (5)
C5—C6	1.531 (6)	C14'—C15'^v	1.50 (5)
C5—H5	0.9800	C14'—H14'	0.9300
C6—C7	1.525 (6)	C15'—C14'^v	1.50 (5)
C6—H6A	0.9700	C15'—H15'	0.9300
C6—H6B	0.9700

N1—Ni—O2ⁱ	95.33 (16)	C6—C7—H7B	109.2
N1—Ni—O3ⁱⁱ	100.50 (16)	C2—C7—H7B	109.2
O2ⁱ—Ni—O3ⁱⁱ	89.68 (14)	H7A—C7—H7B	107.9
N1—Ni—O1	96.72 (16)	O4—C8—O3	122.9 (4)
O2ⁱ—Ni—O1	167.83 (12)	O4—C8—C5	118.1 (4)
O3ⁱⁱ—Ni—O1	89.76 (14)	O3—C8—C5	119.0 (4)
N1—Ni—O4ⁱⁱⁱ	92.29 (16)	C10—C9—N1	108.5 (6)
O2ⁱ—Ni—O4ⁱⁱⁱ	89.74 (14)	C10—C9—H9	125.7
O3ⁱⁱ—Ni—O4ⁱⁱⁱ	167.19 (14)	N1—C9—H9	125.7
O1—Ni—O4ⁱⁱⁱ	88.12 (13)	N2—C10—N2	0.00 (18)
N1—Ni—Niⁱ	159.62 (13)	N2—C10—C9	108.3 (5)
O2ⁱ—Ni—Niⁱ	83.45 (9)	N2'—C10—C9	108.3 (5)
O3ⁱⁱ—Ni—Niⁱ	99.83 (10)	N2—C10—H10	125.9
O1—Ni—Niⁱ	84.67 (9)	N2'—C10—H10	125.9
O4ⁱⁱⁱ—Ni—Niⁱ	67.40 (10)	C9—C10—H10	125.9
C1—O1—Ni	122.0 (3)	N1—C11—N2	110.5 (6)
C1—O2—Niⁱ	124.7 (3)	N1—C11—N2'	110.5 (6)
C8—O3—Ni^iv	106.2 (3)	N2—C11—N2	0.0 (3)
C8—O4—Niⁱⁱⁱ	143.4 (3)	N1—C11—H11	124.7
C11—N1—C9	106.2 (5)	N2—C11—H11	124.7
C11—N1—Ni	125.6 (4)	N2'—C11—H11	124.7
C9—N1—Ni	128.2 (4)	C10—N2—C11	106.4 (5)
O2—C1—O1	124.8 (4)	C10—N2—C12	114.4 (8)
O2—C1—C2	117.1 (4)	C11—N2—C12	139.1 (8)
O1—C1—C2	118.1 (4)	N2—C12—C13	112.9 (15)
C1—C2—C3	112.5 (4)	N2—C12—H12A	109.0
C1—C2—C7	112.5 (4)	C13—C12—H12A	109.0
C3—C2—C7	109.7 (3)	N2'—C12—H12B	109.0
C1—C2—H2	107.3	C13—C12—H12B	109.0
C3—C2—H2	107.3	H12A—C12—H12B	107.8
C7—C2—H2	107.3	C14—C13—C15	121 (2)
C4—C3—C2	112.4 (4)	C14—C13—C12	119 (2)
C4—C3—H3A	109.1	C15—C13—C12	120.2 (18)
C2—C3—H3A	109.1	C13—C14—C15^v	105 (3)
C4—C3—H3B	109.1	C13—C14—H14	127.7
C2—C3—H3B	109.1	C15^v—C14—H14	127.7
H3A—C3—H3B	107.9	C13—C15—C14^v	131 (3)
C3—C4—C5	110.5 (4)	C13—C15—H15	114.6
C3—C4—H4A	109.6	C14^v—C15—H15	114.6
C5—C4—H4A	109.6	C10—N2—C11	106.4 (5)
C3—C4—H4B	109.6	C10—N2—C12'	141.6 (8)
C5—C4—H4B	109.6	C11—N2—C12'	111.8 (9)
H4A—C4—H4B	108.1	C13'—C12'—N2	109.7 (13)
C8—C5—C4	113.8 (4)	C13'—C12'—H12C	109.7
C8—C5—C6	113.3 (4)	N2'—C12'—H12C	109.7
C4—C5—C6	110.4 (3)	C13'—C12'—H12D	109.7
C8—C5—H5	106.2	N2'—C12'—H12D	109.7
C4—C5—H5	106.2	H12C—C12'—H12D	108.2
C6—C5—H5	106.2	C15'—C13'—C14'	119 (2)
C7—C6—C5	111.1 (4)	C15'—C13'—C12'	118.9 (18)
C7—C6—H6A	109.4	C14'—C13'—C12'	122 (2)
C5—C6—H6A	109.4	C13'—C14'—C15'^v	131 (2)
C7—C6—H6B	109.4	C13'—C14'—H14'	114.4
C5—C6—H6B	109.4	C15'^v—C14'—H14'	114.4
H6A—C6—H6B	108.0	C13'—C15'—C14'^v	106 (2)
C6—C7—C2	112.0 (4)	C13'—C15'—H15'	126.8
C6—C7—H7A	109.2	C14'^v—C15'—H15'	126.8
C2—C7—H7A	109.2

N1—Ni—O1—C1	−153.4 (3)	C11—N1—C9—C10	0.4 (6)
O2ⁱ—Ni—O1—C1	18.7 (8)	Ni—N1—C9—C10	179.5 (4)
O3ⁱⁱ—Ni—O1—C1	106.0 (3)	N1—C9—C10—N2	−1.1 (7)
O4ⁱⁱⁱ—Ni—O1—C1	−61.3 (3)	N1—C9—C10—N2'	−1.1 (7)
Niⁱ—Ni—O1—C1	6.1 (3)	C9—N1—C11—N2	0.4 (6)
O2ⁱ—Ni—N1—C11	−144.6 (5)	Ni—N1—C11—N2	−178.7 (3)
O3ⁱⁱ—Ni—N1—C11	124.7 (5)	C9—N1—C11—N2'	0.4 (6)
O1—Ni—N1—C11	33.7 (5)	Ni—N1—C11—N2'	−178.7 (3)
O4ⁱⁱⁱ—Ni—N1—C11	−54.7 (5)	N2—C10—N2—C11	0 (100)
Niⁱ—Ni—N1—C11	−59.1 (7)	C9—C10—N2—C11	1.3 (7)
O2ⁱ—Ni—N1—C9	36.5 (5)	N2—C10—N2'—C12	0 (100)
O3ⁱⁱ—Ni—N1—C9	−54.2 (5)	C9—C10—N2'—C12	−177.6 (9)
O1—Ni—N1—C9	−145.2 (5)	N1—C11—N2—C10	−1.1 (6)
O4ⁱⁱⁱ—Ni—N1—C9	126.4 (5)	N2—C11—N2—C10	0 (100)
Niⁱ—Ni—N1—C9	122.0 (5)	N1—C11—N2'—C12	177.4 (12)
Niⁱ—O2—C1—O1	4.6 (6)	N2—C11—N2'—C12	0 (100)
Niⁱ—O2—C1—C2	−177.0 (3)	C10—N2—C12—C13	−82.7 (13)
Ni—O1—C1—O2	−8.1 (6)	C11—N2—C12—C13	98.9 (15)
Ni—O1—C1—C2	173.4 (3)	N2—C12—C13—C14	124 (2)
O2—C1—C2—C3	153.7 (4)	N2—C12—C13—C15	−55 (2)
O1—C1—C2—C3	−27.8 (5)	C15—C13—C14—C15^v	−19 (3)
O2—C1—C2—C7	29.2 (5)	C12—C13—C14—C15^v	162.1 (17)
O1—C1—C2—C7	−152.3 (4)	C14—C13—C15—C14^v	24 (4)
C1—C2—C3—C4	−70.5 (5)	C12—C13—C15—C14^v	−157 (2)
C7—C2—C3—C4	55.6 (5)	N2—C10—N2—C11	0 (100)
C2—C3—C4—C5	−57.3 (5)	C9—C10—N2—C11	1.3 (7)
C3—C4—C5—C8	−174.8 (4)	N2—C10—N2'—C12'	0 (100)
C3—C4—C5—C6	56.5 (5)	C9—C10—N2'—C12'	176.8 (11)
C8—C5—C6—C7	174.9 (3)	N1—C11—N2—C10	−1.1 (6)
C4—C5—C6—C7	−56.2 (5)	N2—C11—N2—C10	0 (100)
C5—C6—C7—C2	55.8 (5)	N1—C11—N2'—C12'	−178.1 (8)
C1—C2—C7—C6	71.4 (5)	N2—C11—N2'—C12'	0 (100)
C3—C2—C7—C6	−54.6 (5)	C10—N2'—C12'—C13'	−62.7 (19)
Niⁱⁱⁱ—O4—C8—O3	8.4 (8)	C11—N2'—C12'—C13'	112.6 (15)
Niⁱⁱⁱ—O4—C8—C5	−169.0 (3)	N2'—C12'—C13'—C15'	−86 (2)
Ni^iv—O3—C8—O4	−4.3 (5)	N2'—C12'—C13'—C14'	94.8 (19)
Ni^iv—O3—C8—C5	173.0 (3)	C15'—C13'—C14'—C15'^v	22 (4)
C4—C5—C8—O4	−154.6 (4)	C12'—C13'—C14'—C15'^v	−159 (2)
C6—C5—C8—O4	−27.4 (5)	C14'—C13'—C15'—C14'^v	−17 (3)
C4—C5—C8—O3	27.9 (5)	C12'—C13'—C15'—C14'^v	163.9 (16)
C6—C5—C8—O3	155.1 (4)

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x+1, y, z; (iii) −x+1, −y+1, −z+1; (iv) x−1, y, z; (v) −x+1, −y, −z+2.

Experimental details

Crystal data
Chemical formula	[Ni₂(C₈H₁₀O₄)₂(C₁₄H₁₄N₄)]
M_r	696.03
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.4966 (6), 8.8076 (6), 10.7327 (8)
α, β, γ (°)	93.567 (6), 100.608 (6), 105.807 (6)
V (Å³)	754.22 (9)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.31
Crystal size (mm)	0.31 × 0.22 × 0.18

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.557, 0.791
No. of measured, independent and observed [I > 2σ(I)] reflections	6115, 2640, 2287
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.139, 1.11
No. of reflections	2640
No. of parameters	224
No. of restraints	36
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.30, −1.25

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006).

Acknowledgements

The authors thank Henan University of Urban Construction for supporting this work.

References

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