Bis[μ-2-(2,4-difluoro­phen­yl)-1,3-bis­(1,2,4-triazol-1-yl)propan-2-olato-κ4N2,O:O,N2′]bis­[(acetato-κ2O,O′)nickel(II)] methanol hemisolvate

Zhang, F.; Hu, F.-L.; Huang, Z.-J.; Zhuang, J.-C.; Zhuang, Y.

doi:10.1107/S160053680905377X

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Pages m75-m76

doi:10.1107/S160053680905377X

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Bis[μ-2-(2,4-difluorophenyl)-1,3-bis(1,2,4-triazol-1-yl)propan-2-olato-κ⁴N²,O:O,N^2′]bis[(acetato-κ²O,O′)nickel(II)] methanol hemisolvate

Feng Zhang,^a Fei-Long Hu,^a Zhong-Jing Huang,^a ^* Ji-Chang Zhuang ^a and Yue Zhuang ^a

^aDepartment of Chemistry, Guangxi University for Nationalities, Nanning 530006, People's Republic of China
^*Correspondence e-mail: zhongjinghuang@yahoo.cn

(Received 17 October 2009; accepted 14 December 2009; online 19 December 2009)

In the title complex, [Ni₂(C₁₃H₁₁F₂N₆O)₂(C₂H₃O₂)₂]·0.5CH₃OH, there are two half-molecules in the asymmetric unit. The two centrosymmetrically related Ni^II atoms, each attached to an acetate ligand, are linked by two fluconazole ligands. Each Ni^II atom is six-coordinated in a distorted octahedral geometry by two N atoms of the triazole groups and two bridging O atoms from two different fluconazole ligands and two O atoms from a chelating acetate ligand. In the crystal structure, the half-occupied methanol solvent molecule is linked to a triazole group via an O—H⋯N hydrogen bond.

Related literature

Fluconazole, 2-(2,4-difluorophenyl)-1,3-bis(1,2,4-triazol-1-yl)-propan-2-ol, is used to treat invasive infections and is an effective agent in preventing invasive infections in patients undergoing bone marrow transplantation, see: Goodman et al. (1992 ). For general background to interactions between metal ions and drugs, see: Agh-Atabay et al. (2003 ); Ali et al. (2002 ); Castilo-Blum & Barba-Behrens (2000 ); Inoue et al. (2002 ); Patel et al. (2002 ); Tavman et al. (2000 ).

Experimental

Crystal data

[Ni₂(C₁₃H₁₁F₂N₆O)₂(C₂H₃O₂)₂]·0.5CH₄O
M_r = 862.08
Triclinic, $[P \overline 1]$
a = 11.3898 (12) Å
b = 12.4447 (14) Å
c = 14.0012 (16) Å
α = 65.211 (1)°
β = 86.815 (2)°
γ = 88.100 (2)°
V = 1798.8 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.13 mm⁻¹
T = 298 K
0.42 × 0.37 × 0.35 mm

Data collection

Siemens SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.648, T_max = 0.693
9439 measured reflections
6256 independent reflections
4649 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.127
S = 0.97
6256 reflections
508 parameters
H-atom parameters constrained
Δρ_max = 1.09 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Selected bond lengths (Å)

Ni1—O1	2.008 (3)
Ni1—O1ⁱ	2.053 (3)
Ni1—O3	2.050 (3)
Ni1—O4	2.202 (3)
Ni1—N2	2.085 (3)
Ni1—N5ⁱ	2.076 (3)
Ni2—O2	2.033 (3)
Ni2—O2ⁱⁱ	2.030 (3)
Ni2—O5	2.112 (3)
Ni2—O6	2.108 (3)
Ni2—N8	2.089 (3)
Ni2—N11ⁱⁱ	2.067 (3)
Symmetry codes: (i) -x, -y, -z; (ii) -x+1, -y+1, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7⋯N9ⁱⁱⁱ	0.82	2.06	2.861 (11)	166
Symmetry code: (iii) x, y, z+1.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); 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/S160053680905377X/hy2245sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680905377X/hy2245Isup2.hkl

checkCIF report

Comment top

Fluconazole, 2-(2,4-difluorophenyl)-1,3-bis(1,2,4-triazol-1-yl)-propan-2-ol, is one of the first-line popular drugs used to treat invasive infections and is an effective way in preventing invasive infections in patients undergoing bone marrow transplantation (Goodman et al., 1992). With two symmetrical 1,2,4-triazole groups, fluconazole shows structural flexibility and can form stable complexes with various transition metal ions. Recent years, interactions between metal ions and drugs have become of great interesting (Ali et al., 2002). In some ways, the highest activity of a drug is associated with the existence of a metal ion (Agh-Atabay et al., 2003; Castilo-Blum & Barba-Behrens, 2000; Inoue et al., 2002; Patel et al., 2002; Tavman et al., 2000). We report here the structure of the title compound.

The molecular structure of the complex is shown in Fig. 1. The asymmetric unit contains two Ni^II ions, two fluconazole ligands, two bidentate coordinated acetate ligands and a half-occupied solvent methanol molecule. Each fluconazole ligand links the Ni^II centers via its deprotonated hydroxyl group and two triazole groups. The Ni^II center exhibits a distorted octahedral geometry, defined by two N atoms of the triazole ligands and two O atoms of the deprotonated hydroxyl groups from two different fluconazole ligands, and two O atoms from the acetate ligand (Table 1). The Ni1···Ni1ⁱ and Ni2···Ni2ⁱⁱ distances are 3.0974 (7) and 3.0735 (7) Å, respectively [symmetry codes: (i) -x, -y, -z; (ii) 1-x, 1-y, 1-z]. The dihedral angles between the two triazole planes in the same fluconazole ligand are 65.6 (2) and 64.5 (2)°. The two opposite triazole planes in different ligands are parallel. As shown in Fig. 2 and Table 2, hydrogen bond is observed between the triazole group and the methanol molecule.

Related literature top

Fluconazole, 2-(2,4-difluorophenyl)-1,3-bis(1,2,4-triazol-1-yl)-propan-2-ol, is used to treat invasive infections and is an effective way in preventing invasive infections in patients undergoing bone marrow transplantation, see: Goodman et al. (1992). For general background to interactions between metal ions and drugs, see: Agh-Atabay et al. (2003); Ali et al. (2002); Castilo-Blum & Barba-Behrens (2000); Inoue et al. (2002); Patel et al. (2002); Tavman et al. (2000).

Experimental top

A mixture of Ni(CH₃CO₂)₂.4H₂O (0.125 g, 0.5 mmol), fluconazole (0.153 g, 0.5 mmol) and methanol (15 ml) was heated in a Teflon-lined steel bomb at 423K for 3 d. The green crystals were collected, washed with DMF and dried in air. Analysis, calculated for C_30.5H₃₀F₄N₁₂Ni₂O_6.5: C 42.48, N 19.50, H 3.48%; found: C 42.61, N 19.41, H 3.53%.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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. Molecular structure of the title compound. [Symmetry codes: (i) -x, -y, -z; (ii) 1-x, 1-y, 1-z.]
	Fig. 2. Crystal packing of the title compound, viewed down the a axis. Dashed lines indicate hydrongen bonds. H atoms have been omitted.

Bis[µ-2-(2,4-difluorophenyl)-1,3-bis(1,2,4-triazol-1-yl)propan-2-olato- κ⁴N²,O:O,N^2']bis[(acetato- κ²O,O')nickel(II)] methanol hemisolvate top

Crystal data top

[Ni₂(C₁₃H₁₁F₂N₆O)₂(C₂H₃O₂)₂]·0.5CH₄O	Z = 2
M_r = 862.08	F(000) = 882
Triclinic, P1	D_x = 1.592 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.3898 (12) Å	Cell parameters from 3550 reflections
b = 12.4447 (14) Å	θ = 2.5–27.9°
c = 14.0012 (16) Å	µ = 1.13 mm⁻¹
α = 65.211 (1)°	T = 298 K
β = 86.815 (2)°	Block, green
γ = 88.100 (2)°	0.42 × 0.37 × 0.35 mm
V = 1798.8 (3) Å³

Data collection top

Siemens SMART 1000 CCD diffractometer	6256 independent reflections
Radiation source: fine-focus sealed tube	4649 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→11
T_min = 0.648, T_max = 0.693	k = −13→14
9439 measured reflections	l = −16→16

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.058P)² + 3.8657P] where P = (F_o² + 2F_c²)/3
6256 reflections	(Δ/σ)_max = 0.001
508 parameters	Δρ_max = 1.09 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

[Ni₂(C₁₃H₁₁F₂N₆O)₂(C₂H₃O₂)₂]·0.5CH₄O	γ = 88.100 (2)°
M_r = 862.08	V = 1798.8 (3) Å³
Triclinic, P1	Z = 2
a = 11.3898 (12) Å	Mo Kα radiation
b = 12.4447 (14) Å	µ = 1.13 mm⁻¹
c = 14.0012 (16) Å	T = 298 K
α = 65.211 (1)°	0.42 × 0.37 × 0.35 mm
β = 86.815 (2)°

Data collection top

Siemens SMART 1000 CCD diffractometer	6256 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4649 reflections with I > 2σ(I)
T_min = 0.648, T_max = 0.693	R_int = 0.018
9439 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 0.97	Δρ_max = 1.09 e Å⁻³
6256 reflections	Δρ_min = −0.30 e Å⁻³
508 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ni1	−0.01760 (4)	−0.09636 (4)	0.11391 (4)	0.03078 (15)
Ni2	0.62054 (4)	0.55904 (4)	0.46306 (4)	0.03113 (15)
F1	0.1595 (3)	0.3241 (3)	0.1388 (3)	0.0802 (10)
F2	−0.2181 (4)	0.4782 (4)	0.1417 (4)	0.1098 (14)
F3	0.3015 (3)	0.9504 (3)	0.3828 (2)	0.0719 (9)
F4	0.3922 (4)	0.9592 (3)	0.7008 (3)	0.1012 (13)
N1	0.0516 (3)	0.0015 (3)	0.2632 (3)	0.0373 (8)
N2	−0.0209 (3)	−0.0787 (3)	0.2557 (3)	0.0377 (8)
N3	−0.0622 (4)	−0.0612 (4)	0.4067 (3)	0.0528 (10)
N7	0.4966 (3)	0.7223 (3)	0.2737 (3)	0.0348 (8)
N8	0.5773 (3)	0.6318 (3)	0.3051 (3)	0.0372 (8)
N9	0.5101 (4)	0.6616 (4)	0.1477 (3)	0.0507 (10)
O1	0.0197 (2)	0.0766 (2)	0.03910 (19)	0.0294 (6)
O2	0.4526 (2)	0.6025 (2)	0.4913 (2)	0.0311 (6)
O3	−0.0020 (3)	−0.2773 (3)	0.1774 (2)	0.0446 (7)
O4	0.1604 (3)	−0.1751 (2)	0.1378 (2)	0.0421 (7)
O5	0.7026 (3)	0.7080 (3)	0.4645 (2)	0.0421 (7)
O6	0.6725 (3)	0.5479 (2)	0.6091 (2)	0.0401 (7)
O7	0.5255 (11)	0.7012 (13)	0.9308 (7)	0.121 (4)	0.50
H7	0.5119	0.6988	0.9897	0.181*	0.50
C1	−0.0878 (4)	−0.1130 (4)	0.3437 (3)	0.0454 (11)
H1	−0.1473	−0.1682	0.3603	0.054*
C2	0.0249 (4)	0.0102 (4)	0.3538 (3)	0.0470 (11)
H2	0.0625	0.0598	0.3766	0.056*
C3	0.1393 (4)	0.0623 (4)	0.1802 (3)	0.0373 (10)
H3A	0.1898	0.0041	0.1686	0.045*
H3B	0.1879	0.1094	0.2025	0.045*
C4	0.0834 (3)	0.1436 (3)	0.0756 (3)	0.0319 (9)
C8	0.0046 (4)	0.2366 (4)	0.0923 (3)	0.0373 (10)
C9	0.0427 (4)	0.3203 (4)	0.1237 (4)	0.0502 (12)
C10	−0.0297 (5)	0.4014 (5)	0.1419 (5)	0.0709 (17)
H10	−0.0005	0.4559	0.1637	0.085*
C11	−0.1454 (5)	0.3975 (5)	0.1262 (5)	0.0693 (16)
C12	−0.1914 (5)	0.3185 (5)	0.0951 (5)	0.0607 (14)
H12	−0.2714	0.3182	0.0852	0.073*
C13	−0.1144 (4)	0.2385 (4)	0.0785 (4)	0.0444 (11)
H13	−0.1444	0.1839	0.0572	0.053*
C14	0.1097 (4)	−0.2731 (4)	0.1687 (3)	0.0409 (10)
C15	0.1762 (5)	−0.3857 (4)	0.1921 (4)	0.0600 (14)
H15A	0.1644	−0.4123	0.1382	0.090*
H15B	0.1485	−0.4447	0.2591	0.090*
H15C	0.2584	−0.3727	0.1943	0.090*
C16	0.5812 (4)	0.5993 (4)	0.2270 (3)	0.0443 (11)
H16	0.6293	0.5377	0.2264	0.053*
C17	0.4589 (4)	0.7378 (4)	0.1811 (3)	0.0426 (10)
H17	0.4037	0.7948	0.1441	0.051*
C18	0.4701 (4)	0.7880 (3)	0.3375 (3)	0.0353 (9)
H18A	0.4257	0.8591	0.2970	0.042*
H18B	0.5430	0.8118	0.3553	0.042*
C19	0.3983 (3)	0.7124 (3)	0.4401 (3)	0.0325 (9)
C23	0.3932 (4)	0.7800 (4)	0.5102 (3)	0.0370 (10)
C24	0.3472 (4)	0.8938 (4)	0.4802 (4)	0.0489 (12)
C25	0.3445 (5)	0.9556 (5)	0.5418 (4)	0.0638 (15)
H25	0.3127	1.0317	0.5188	0.077*
C26	0.3907 (5)	0.8997 (5)	0.6383 (5)	0.0643 (15)
C27	0.4371 (5)	0.7879 (5)	0.6747 (4)	0.0603 (14)
H27	0.4677	0.7520	0.7412	0.072*
C28	0.4374 (4)	0.7296 (4)	0.6095 (3)	0.0461 (11)
H28	0.4686	0.6533	0.6337	0.055*
C29	0.7118 (4)	0.6521 (4)	0.5628 (4)	0.0407 (10)
C30	0.7676 (5)	0.7072 (5)	0.6254 (4)	0.0596 (14)
H30A	0.8297	0.6565	0.6646	0.089*
H30B	0.7096	0.7180	0.6732	0.089*
H30C	0.7994	0.7827	0.5786	0.089*
C31	0.554 (2)	0.585 (2)	0.9393 (17)	0.160 (9)	0.50
H31A	0.6279	0.5598	0.9716	0.240*	0.50
H31B	0.5588	0.5856	0.8703	0.240*	0.50
H31C	0.4936	0.5312	0.9816	0.240*	0.50
N10	0.1984 (3)	0.6289 (3)	0.5011 (3)	0.0421 (9)
N11	0.2213 (3)	0.5129 (3)	0.5628 (3)	0.0390 (8)
N12	0.0551 (4)	0.5703 (4)	0.6210 (4)	0.0704 (14)
C20	0.2747 (4)	0.6961 (4)	0.4094 (3)	0.0409 (10)
H20A	0.2394	0.7732	0.3703	0.049*
H20B	0.2814	0.6552	0.3636	0.049*
C21	0.1330 (4)	0.4827 (4)	0.6329 (4)	0.0519 (12)
H21	0.1250	0.4069	0.6864	0.062*
H22	0.0654	0.7341	0.5096	0.062*
C22	0.0994 (5)	0.6589 (5)	0.5386 (4)	0.0637 (15)
N4	0.2486 (3)	0.1225 (3)	−0.0388 (3)	0.0332 (8)
N5	0.1993 (3)	0.0854 (3)	−0.1060 (3)	0.0377 (8)
N6	0.3799 (3)	0.0060 (4)	−0.0680 (3)	0.0539 (10)
C5	0.1863 (4)	0.2054 (4)	−0.0048 (3)	0.0359 (9)
H5A	0.1556	0.2707	−0.0655	0.043*
H5B	0.2406	0.2373	0.0275	0.043*
C6	0.2825 (4)	0.0161 (4)	−0.1201 (4)	0.0467 (11)
H6	0.2737	−0.0229	−0.1632	0.056*
C7	0.3550 (4)	0.0744 (4)	−0.0177 (4)	0.0461 (11)
H7A	0.4056	0.0868	0.0265	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0273 (3)	0.0317 (3)	0.0295 (3)	−0.0020 (2)	−0.0011 (2)	−0.0089 (2)
Ni2	0.0284 (3)	0.0302 (3)	0.0311 (3)	0.0001 (2)	0.0014 (2)	−0.0095 (2)
F1	0.056 (2)	0.104 (3)	0.123 (3)	−0.0002 (17)	−0.0196 (19)	−0.088 (2)
F2	0.095 (3)	0.112 (3)	0.165 (4)	0.031 (2)	0.008 (3)	−0.103 (3)
F3	0.094 (2)	0.0541 (18)	0.066 (2)	0.0376 (17)	−0.0221 (17)	−0.0239 (16)
F4	0.161 (4)	0.088 (3)	0.084 (3)	0.006 (2)	0.010 (2)	−0.067 (2)
N1	0.0351 (19)	0.042 (2)	0.0330 (19)	−0.0058 (16)	−0.0044 (15)	−0.0137 (16)
N2	0.036 (2)	0.043 (2)	0.0312 (18)	−0.0036 (16)	−0.0030 (15)	−0.0123 (16)
N3	0.056 (3)	0.063 (3)	0.039 (2)	−0.008 (2)	0.0062 (19)	−0.022 (2)
N7	0.0362 (19)	0.0324 (18)	0.0304 (18)	0.0010 (15)	0.0033 (15)	−0.0085 (15)
N8	0.037 (2)	0.038 (2)	0.0330 (19)	0.0040 (16)	0.0025 (15)	−0.0121 (16)
N9	0.059 (3)	0.054 (2)	0.039 (2)	0.004 (2)	−0.0032 (19)	−0.0193 (19)
O1	0.0304 (14)	0.0292 (14)	0.0286 (14)	−0.0036 (11)	−0.0009 (11)	−0.0118 (11)
O2	0.0297 (14)	0.0263 (14)	0.0338 (15)	0.0024 (11)	0.0009 (11)	−0.0094 (12)
O3	0.0375 (18)	0.0379 (17)	0.0458 (18)	−0.0038 (13)	−0.0062 (14)	−0.0044 (14)
O4	0.0372 (17)	0.0329 (16)	0.0531 (18)	−0.0034 (13)	−0.0038 (14)	−0.0146 (14)
O5	0.0420 (17)	0.0402 (17)	0.0379 (17)	−0.0049 (13)	−0.0026 (13)	−0.0099 (14)
O6	0.0422 (17)	0.0387 (17)	0.0360 (16)	0.0000 (13)	−0.0043 (13)	−0.0119 (13)
O7	0.147 (10)	0.180 (12)	0.052 (5)	−0.008 (9)	−0.021 (6)	−0.062 (7)
C1	0.044 (3)	0.052 (3)	0.034 (2)	−0.009 (2)	0.002 (2)	−0.012 (2)
C2	0.051 (3)	0.052 (3)	0.040 (3)	−0.004 (2)	−0.002 (2)	−0.021 (2)
C3	0.029 (2)	0.043 (2)	0.037 (2)	−0.0041 (18)	−0.0032 (17)	−0.0137 (19)
C4	0.029 (2)	0.034 (2)	0.035 (2)	−0.0022 (17)	−0.0012 (17)	−0.0154 (18)
C8	0.036 (2)	0.039 (2)	0.039 (2)	0.0019 (18)	0.0000 (18)	−0.018 (2)
C9	0.046 (3)	0.058 (3)	0.060 (3)	−0.001 (2)	−0.001 (2)	−0.038 (3)
C10	0.074 (4)	0.070 (4)	0.096 (5)	−0.001 (3)	0.005 (3)	−0.062 (4)
C11	0.067 (4)	0.066 (4)	0.089 (4)	0.017 (3)	0.010 (3)	−0.050 (3)
C12	0.045 (3)	0.063 (3)	0.081 (4)	0.010 (2)	0.005 (3)	−0.039 (3)
C13	0.037 (3)	0.045 (3)	0.055 (3)	0.001 (2)	0.002 (2)	−0.026 (2)
C14	0.043 (3)	0.037 (2)	0.038 (2)	0.006 (2)	−0.0127 (19)	−0.010 (2)
C15	0.058 (3)	0.042 (3)	0.078 (4)	0.011 (2)	−0.027 (3)	−0.021 (3)
C16	0.052 (3)	0.042 (3)	0.040 (3)	0.006 (2)	0.005 (2)	−0.019 (2)
C17	0.044 (3)	0.045 (3)	0.032 (2)	0.006 (2)	−0.0033 (19)	−0.010 (2)
C18	0.038 (2)	0.031 (2)	0.033 (2)	0.0030 (18)	0.0007 (18)	−0.0102 (18)
C19	0.032 (2)	0.028 (2)	0.034 (2)	0.0037 (16)	−0.0014 (17)	−0.0104 (17)
C23	0.037 (2)	0.037 (2)	0.036 (2)	0.0045 (18)	0.0030 (18)	−0.0158 (19)
C24	0.057 (3)	0.044 (3)	0.045 (3)	0.012 (2)	−0.002 (2)	−0.018 (2)
C25	0.082 (4)	0.046 (3)	0.066 (4)	0.015 (3)	0.009 (3)	−0.028 (3)
C26	0.083 (4)	0.058 (3)	0.065 (4)	0.000 (3)	0.016 (3)	−0.042 (3)
C27	0.081 (4)	0.059 (3)	0.046 (3)	0.005 (3)	0.001 (3)	−0.027 (3)
C28	0.054 (3)	0.045 (3)	0.040 (3)	0.003 (2)	0.003 (2)	−0.020 (2)
C29	0.034 (2)	0.041 (3)	0.049 (3)	0.0045 (19)	−0.0088 (19)	−0.020 (2)
C30	0.067 (4)	0.056 (3)	0.062 (3)	0.000 (3)	−0.018 (3)	−0.029 (3)
C31	0.17 (2)	0.19 (2)	0.128 (17)	−0.004 (18)	−0.048 (15)	−0.066 (17)
N10	0.033 (2)	0.040 (2)	0.045 (2)	0.0059 (16)	0.0001 (16)	−0.0105 (17)
N11	0.0305 (19)	0.037 (2)	0.041 (2)	0.0028 (15)	0.0041 (15)	−0.0082 (16)
N12	0.049 (3)	0.065 (3)	0.074 (3)	0.013 (2)	0.019 (2)	−0.011 (2)
C20	0.040 (2)	0.036 (2)	0.035 (2)	0.0034 (19)	−0.0007 (19)	−0.0040 (19)
C21	0.039 (3)	0.050 (3)	0.053 (3)	0.001 (2)	0.008 (2)	−0.009 (2)
C22	0.045 (3)	0.059 (3)	0.071 (4)	0.020 (3)	0.006 (3)	−0.013 (3)
N4	0.0221 (17)	0.0383 (19)	0.0385 (19)	−0.0034 (14)	−0.0008 (14)	−0.0153 (16)
N5	0.0255 (18)	0.047 (2)	0.043 (2)	−0.0037 (15)	0.0036 (15)	−0.0224 (17)
N6	0.032 (2)	0.062 (3)	0.072 (3)	0.0084 (18)	0.0005 (19)	−0.033 (2)
C5	0.032 (2)	0.036 (2)	0.040 (2)	−0.0021 (18)	0.0008 (18)	−0.0162 (19)
C6	0.035 (3)	0.054 (3)	0.057 (3)	0.000 (2)	0.008 (2)	−0.031 (2)
C7	0.029 (2)	0.054 (3)	0.054 (3)	−0.004 (2)	−0.001 (2)	−0.021 (2)

Geometric parameters (Å, º) top

Ni1—O1	2.008 (3)	C12—H12	0.9300
Ni1—O1ⁱ	2.053 (3)	C13—H13	0.9300
Ni1—O3	2.050 (3)	C14—C15	1.489 (6)
Ni1—O4	2.202 (3)	C15—H15A	0.9600
Ni1—N2	2.085 (3)	C15—H15B	0.9600
Ni1—N5ⁱ	2.076 (3)	C15—H15C	0.9600
Ni2—O2	2.033 (3)	C16—H16	0.9300
Ni2—O2ⁱⁱ	2.030 (3)	C17—H17	0.9300
Ni2—O5	2.112 (3)	C18—C19	1.552 (5)
Ni2—O6	2.108 (3)	C18—H18A	0.9700
Ni2—N8	2.089 (3)	C18—H18B	0.9700
Ni2—N11ⁱⁱ	2.067 (3)	C19—C23	1.535 (6)
F1—C9	1.364 (6)	C19—C20	1.538 (6)
F2—C11	1.360 (6)	C23—C28	1.381 (6)
F3—C24	1.368 (5)	C23—C24	1.390 (6)
F4—C26	1.365 (6)	C24—C25	1.375 (7)
N1—C2	1.335 (5)	C25—C26	1.360 (8)
N1—N2	1.357 (5)	C25—H25	0.9300
N1—C3	1.450 (5)	C26—C27	1.365 (7)
N2—C1	1.325 (5)	C27—C28	1.383 (6)
N3—C2	1.321 (6)	C27—H27	0.9300
N3—C1	1.340 (6)	C28—H28	0.9300
N7—C17	1.323 (5)	C29—C30	1.497 (6)
N7—N8	1.367 (5)	C30—H30A	0.9600
N7—C18	1.457 (5)	C30—H30B	0.9600
N8—C16	1.314 (5)	C30—H30C	0.9600
N9—C17	1.328 (6)	C31—H31A	0.9600
N9—C16	1.351 (6)	C31—H31B	0.9600
O1—C4	1.387 (5)	C31—H31C	0.9600
O1—Ni1ⁱ	2.053 (3)	N10—C22	1.325 (6)
O2—C19	1.392 (4)	N10—N11	1.361 (5)
O2—Ni2ⁱⁱ	2.030 (3)	N10—C20	1.459 (5)
O3—C14	1.272 (5)	N11—C21	1.312 (5)
O4—C14	1.259 (5)	N11—Ni2ⁱⁱ	2.067 (3)
O5—C29	1.264 (5)	N12—C22	1.307 (7)
O6—C29	1.266 (5)	N12—C21	1.342 (6)
O7—C31	1.43 (2)	C20—H20A	0.9700
O7—H7	0.8200	C20—H20B	0.9700
C1—H1	0.9300	C21—H21	0.9300
C2—H2	0.9300	C22—H22	0.9300
C3—C4	1.547 (6)	N4—C7	1.326 (5)
C3—H3A	0.9700	N4—N5	1.363 (5)
C3—H3B	0.9700	N4—C5	1.456 (5)
C4—C8	1.527 (6)	N5—C6	1.322 (5)
C4—C5	1.556 (5)	N5—Ni1ⁱ	2.076 (3)
C8—C13	1.378 (6)	N6—C7	1.329 (6)
C8—C9	1.380 (6)	N6—C6	1.336 (6)
C9—C10	1.378 (7)	C5—H5A	0.9700
C10—C11	1.354 (8)	C5—H5B	0.9700
C10—H10	0.9300	C6—H6	0.9300
C11—C12	1.360 (8)	C7—H7A	0.9300
C12—C13	1.389 (6)

O1—Ni1—O3	162.20 (11)	C14—C15—H15B	109.5
O1—Ni1—O1ⁱ	80.59 (11)	H15A—C15—H15B	109.5
O3—Ni1—O1ⁱ	95.01 (11)	C14—C15—H15C	109.5
O1—Ni1—N5ⁱ	99.07 (12)	H15A—C15—H15C	109.5
O3—Ni1—N5ⁱ	97.64 (13)	H15B—C15—H15C	109.5
O1ⁱ—Ni1—N5ⁱ	84.42 (12)	N8—C16—N9	115.2 (4)
O1—Ni1—N2	88.33 (12)	N8—C16—H16	122.4
O3—Ni1—N2	96.80 (13)	N9—C16—H16	122.4
O1ⁱ—Ni1—N2	168.17 (12)	N7—C17—N9	111.2 (4)
N5ⁱ—Ni1—N2	93.32 (14)	N7—C17—H17	124.4
O1—Ni1—O4	101.03 (10)	N9—C17—H17	124.4
O3—Ni1—O4	61.87 (11)	N7—C18—C19	111.4 (3)
O1ⁱ—Ni1—O4	93.99 (11)	N7—C18—H18A	109.4
N5ⁱ—Ni1—O4	159.30 (12)	C19—C18—H18A	109.4
N2—Ni1—O4	92.17 (13)	N7—C18—H18B	109.4
O2ⁱⁱ—Ni2—O2	81.69 (11)	C19—C18—H18B	109.4
O2ⁱⁱ—Ni2—N11ⁱⁱ	88.38 (12)	H18A—C18—H18B	108.0
O2—Ni2—N11ⁱⁱ	169.91 (12)	O2—C19—C23	110.3 (3)
O2ⁱⁱ—Ni2—N8	98.46 (12)	O2—C19—C20	109.8 (3)
O2—Ni2—N8	85.09 (12)	C23—C19—C20	111.4 (3)
N11ⁱⁱ—Ni2—N8	94.62 (14)	O2—C19—C18	110.0 (3)
O2ⁱⁱ—Ni2—O6	100.48 (11)	C23—C19—C18	107.5 (3)
O2—Ni2—O6	91.88 (11)	C20—C19—C18	107.8 (3)
N11ⁱⁱ—Ni2—O6	91.72 (13)	C28—C23—C24	115.2 (4)
N8—Ni2—O6	160.18 (13)	C28—C23—C19	120.6 (4)
O2ⁱⁱ—Ni2—O5	162.83 (11)	C24—C23—C19	124.2 (4)
O2—Ni2—O5	97.31 (11)	F3—C24—C25	116.6 (4)
N11ⁱⁱ—Ni2—O5	92.72 (13)	F3—C24—C23	119.0 (4)
N8—Ni2—O5	98.53 (12)	C25—C24—C23	124.4 (5)
O6—Ni2—O5	62.37 (11)	C26—C25—C24	116.5 (5)
C2—N1—N2	108.4 (3)	C26—C25—H25	121.7
C2—N1—C3	130.6 (4)	C24—C25—H25	121.7
N2—N1—C3	120.9 (3)	C25—C26—C27	123.2 (5)
C1—N2—N1	103.3 (3)	C25—C26—F4	118.3 (5)
C1—N2—Ni1	137.8 (3)	C27—C26—F4	118.5 (5)
N1—N2—Ni1	118.1 (2)	C26—C27—C28	117.9 (5)
C2—N3—C1	103.2 (4)	C26—C27—H27	121.1
C17—N7—N8	109.0 (3)	C28—C27—H27	121.1
C17—N7—C18	130.7 (4)	C23—C28—C27	122.8 (5)
N8—N7—C18	120.2 (3)	C23—C28—H28	118.6
C16—N8—N7	102.5 (3)	C27—C28—H28	118.6
C16—N8—Ni2	137.4 (3)	O5—C29—O6	119.4 (4)
N7—N8—Ni2	117.4 (2)	O5—C29—C30	121.1 (4)
C17—N9—C16	102.1 (4)	O6—C29—C30	119.5 (4)
C4—O1—Ni1	127.5 (2)	C29—C30—H30A	109.5
C4—O1—Ni1ⁱ	126.3 (2)	C29—C30—H30B	109.5
Ni1—O1—Ni1ⁱ	99.41 (11)	H30A—C30—H30B	109.5
C19—O2—Ni2ⁱⁱ	127.2 (2)	C29—C30—H30C	109.5
C19—O2—Ni2	126.1 (2)	H30A—C30—H30C	109.5
Ni2ⁱⁱ—O2—Ni2	98.31 (11)	H30B—C30—H30C	109.5
C14—O3—Ni1	92.3 (2)	O7—C31—H31A	109.5
C14—O4—Ni1	85.8 (3)	O7—C31—H31B	109.5
C29—O5—Ni2	89.0 (3)	H31A—C31—H31B	109.5
C29—O6—Ni2	89.2 (2)	O7—C31—H31C	109.5
C31—O7—H7	109.5	H31A—C31—H31C	109.5
N2—C1—N3	114.2 (4)	H31B—C31—H31C	109.5
N2—C1—H1	122.9	C22—N10—N11	107.8 (4)
N3—C1—H1	122.9	C22—N10—C20	131.2 (4)
N3—C2—N1	110.9 (4)	N11—N10—C20	120.9 (3)
N3—C2—H2	124.5	C21—N11—N10	103.2 (3)
N1—C2—H2	124.5	C21—N11—Ni2ⁱⁱ	138.1 (3)
N1—C3—C4	112.3 (3)	N10—N11—Ni2ⁱⁱ	118.2 (2)
N1—C3—H3A	109.2	C22—N12—C21	102.5 (4)
C4—C3—H3A	109.2	N10—C20—C19	112.2 (3)
N1—C3—H3B	109.2	N10—C20—H20A	109.2
C4—C3—H3B	109.2	C19—C20—H20A	109.2
H3A—C3—H3B	107.9	N10—C20—H20B	109.2
O1—C4—C8	110.7 (3)	C19—C20—H20B	109.2
O1—C4—C3	109.9 (3)	H20A—C20—H20B	107.9
C8—C4—C3	109.8 (3)	N11—C21—N12	114.5 (4)
O1—C4—C5	109.7 (3)	N11—C21—H21	122.7
C8—C4—C5	109.8 (3)	N12—C21—H21	122.7
C3—C4—C5	106.8 (3)	N12—C22—N10	112.0 (4)
C13—C8—C9	115.3 (4)	N12—C22—H22	124.0
C13—C8—C4	119.8 (4)	N10—C22—H22	124.0
C9—C8—C4	124.8 (4)	C7—N4—N5	108.8 (3)
F1—C9—C10	116.9 (4)	C7—N4—C5	130.5 (4)
F1—C9—C8	118.7 (4)	N5—N4—C5	120.7 (3)
C10—C9—C8	124.4 (5)	C6—N5—N4	102.5 (3)
C11—C10—C9	116.5 (5)	C6—N5—Ni1ⁱ	135.2 (3)
C11—C10—H10	121.7	N4—N5—Ni1ⁱ	117.6 (2)
C9—C10—H10	121.7	C7—N6—C6	102.4 (4)
C10—C11—C12	123.4 (5)	N4—C5—C4	111.0 (3)
C10—C11—F2	117.5 (5)	N4—C5—H5A	109.4
C12—C11—F2	119.1 (6)	C4—C5—H5A	109.4
C11—C12—C13	117.5 (5)	N4—C5—H5B	109.4
C11—C12—H12	121.2	C4—C5—H5B	109.4
C13—C12—H12	121.2	H5A—C5—H5B	108.0
C8—C13—C12	122.8 (5)	N5—C6—N6	115.2 (4)
C8—C13—H13	118.6	N5—C6—H6	122.4
C12—C13—H13	118.6	N6—C6—H6	122.4
O4—C14—O3	119.8 (4)	N4—C7—N6	111.1 (4)
O4—C14—C15	122.1 (4)	N4—C7—H7A	124.5
O3—C14—C15	118.1 (4)	N6—C7—H7A	124.5
C14—C15—H15A	109.5

C2—N1—N2—C1	0.3 (5)	C3—C4—C8—C9	61.4 (5)
C3—N1—N2—C1	−179.3 (4)	C5—C4—C8—C9	−55.8 (6)
C2—N1—N2—Ni1	171.8 (3)	C13—C8—C9—F1	−179.8 (4)
C3—N1—N2—Ni1	−7.7 (5)	C4—C8—C9—F1	1.8 (7)
O1—Ni1—N2—C1	135.6 (5)	C13—C8—C9—C10	0.6 (8)
O3—Ni1—N2—C1	−61.5 (5)	C4—C8—C9—C10	−177.8 (5)
O1ⁱ—Ni1—N2—C1	115.2 (6)	F1—C9—C10—C11	179.7 (5)
N5ⁱ—Ni1—N2—C1	36.6 (5)	C8—C9—C10—C11	−0.7 (9)
O4—Ni1—N2—C1	−123.4 (5)	C9—C10—C11—C12	0.5 (10)
O1—Ni1—N2—N1	−32.0 (3)	C9—C10—C11—F2	−178.8 (5)
O3—Ni1—N2—N1	130.9 (3)	C10—C11—C12—C13	−0.2 (10)
O1ⁱ—Ni1—N2—N1	−52.5 (7)	F2—C11—C12—C13	179.1 (5)
N5ⁱ—Ni1—N2—N1	−131.0 (3)	C9—C8—C13—C12	−0.2 (7)
O4—Ni1—N2—N1	68.9 (3)	C4—C8—C13—C12	178.3 (4)
C17—N7—N8—C16	−0.3 (4)	C11—C12—C13—C8	0.0 (8)
C18—N7—N8—C16	−177.1 (3)	Ni1—O4—C14—O3	−5.0 (4)
C17—N7—N8—Ni2	−165.0 (3)	Ni1—O4—C14—C15	172.7 (4)
C18—N7—N8—Ni2	18.3 (4)	Ni1—O3—C14—O4	5.3 (4)
O2ⁱⁱ—Ni2—N8—C16	−45.9 (5)	Ni1—O3—C14—C15	−172.4 (4)
O2—Ni2—N8—C16	−126.7 (5)	N7—N8—C16—N9	0.3 (5)
N11ⁱⁱ—Ni2—N8—C16	43.2 (5)	Ni2—N8—C16—N9	160.0 (3)
O6—Ni2—N8—C16	151.4 (4)	C17—N9—C16—N8	−0.2 (5)
O5—Ni2—N8—C16	136.6 (4)	N8—N7—C17—N9	0.2 (5)
O2ⁱⁱ—Ni2—N8—N7	111.7 (3)	C18—N7—C17—N9	176.5 (4)
O2—Ni2—N8—N7	30.9 (3)	C16—N9—C17—N7	0.0 (5)
N11ⁱⁱ—Ni2—N8—N7	−159.3 (3)	C17—N7—C18—C19	112.1 (5)
O6—Ni2—N8—N7	−51.0 (5)	N8—N7—C18—C19	−71.9 (4)
O5—Ni2—N8—N7	−65.8 (3)	Ni2ⁱⁱ—O2—C19—C23	116.3 (3)
O3—Ni1—O1—C4	−75.3 (5)	Ni2—O2—C19—C23	−102.6 (3)
O1ⁱ—Ni1—O1—C4	−152.2 (3)	Ni2ⁱⁱ—O2—C19—C20	−6.9 (4)
N5ⁱ—Ni1—O1—C4	125.0 (3)	Ni2—O2—C19—C20	134.2 (3)
N2—Ni1—O1—C4	31.9 (3)	Ni2ⁱⁱ—O2—C19—C18	−125.3 (3)
O4—Ni1—O1—C4	−60.0 (3)	Ni2—O2—C19—C18	15.7 (4)
O3—Ni1—O1—Ni1ⁱ	76.9 (4)	N7—C18—C19—O2	50.3 (4)
O1ⁱ—Ni1—O1—Ni1ⁱ	0.0	N7—C18—C19—C23	170.4 (3)
N5ⁱ—Ni1—O1—Ni1ⁱ	−82.74 (13)	N7—C18—C19—C20	−69.4 (4)
N2—Ni1—O1—Ni1ⁱ	−175.84 (13)	O2—C19—C23—C28	−0.9 (5)
O4—Ni1—O1—Ni1ⁱ	92.27 (12)	C20—C19—C23—C28	121.3 (4)
O2ⁱⁱ—Ni2—O2—C19	−149.6 (3)	C18—C19—C23—C28	−120.8 (4)
N11ⁱⁱ—Ni2—O2—C19	−139.0 (7)	O2—C19—C23—C24	178.1 (4)
N8—Ni2—O2—C19	−50.3 (3)	C20—C19—C23—C24	−59.6 (5)
O6—Ni2—O2—C19	110.1 (3)	C18—C19—C23—C24	58.2 (5)
O5—Ni2—O2—C19	47.7 (3)	C28—C23—C24—F3	−180.0 (4)
O2ⁱⁱ—Ni2—O2—Ni2ⁱⁱ	0.0	C19—C23—C24—F3	0.9 (7)
N11ⁱⁱ—Ni2—O2—Ni2ⁱⁱ	10.5 (7)	C28—C23—C24—C25	0.4 (7)
N8—Ni2—O2—Ni2ⁱⁱ	99.31 (13)	C19—C23—C24—C25	−178.7 (5)
O6—Ni2—O2—Ni2ⁱⁱ	−100.31 (12)	F3—C24—C25—C26	−179.5 (5)
O5—Ni2—O2—Ni2ⁱⁱ	−162.69 (11)	C23—C24—C25—C26	0.1 (8)
O1—Ni1—O3—C14	14.2 (5)	C24—C25—C26—C27	−0.5 (9)
O1ⁱ—Ni1—O3—C14	88.9 (3)	C24—C25—C26—F4	178.4 (5)
N5ⁱ—Ni1—O3—C14	173.9 (3)	C25—C26—C27—C28	0.3 (9)
N2—Ni1—O3—C14	−91.8 (3)	F4—C26—C27—C28	−178.6 (5)
O4—Ni1—O3—C14	−3.0 (2)	C24—C23—C28—C27	−0.5 (7)
O1—Ni1—O4—C14	−171.7 (2)	C19—C23—C28—C27	178.6 (4)
O3—Ni1—O4—C14	3.0 (2)	C26—C27—C28—C23	0.2 (8)
O1ⁱ—Ni1—O4—C14	−90.5 (3)	Ni2—O5—C29—O6	−0.6 (4)
N5ⁱ—Ni1—O4—C14	−5.7 (5)	Ni2—O5—C29—C30	179.8 (4)
N2—Ni1—O4—C14	99.6 (3)	Ni2—O6—C29—O5	0.6 (4)
O2ⁱⁱ—Ni2—O5—C29	3.1 (5)	Ni2—O6—C29—C30	−179.8 (4)
O2—Ni2—O5—C29	88.6 (2)	C22—N10—N11—C21	0.0 (5)
N11ⁱⁱ—Ni2—O5—C29	−90.2 (3)	C20—N10—N11—C21	−177.5 (4)
N8—Ni2—O5—C29	174.7 (3)	C22—N10—N11—Ni2ⁱⁱ	−173.4 (4)
O6—Ni2—O5—C29	0.3 (2)	C20—N10—N11—Ni2ⁱⁱ	9.0 (5)
O2ⁱⁱ—Ni2—O6—C29	−179.5 (2)	C22—N10—C20—C19	116.9 (6)
O2—Ni2—O6—C29	−97.6 (2)	N11—N10—C20—C19	−66.2 (5)
N11ⁱⁱ—Ni2—O6—C29	91.8 (3)	O2—C19—C20—N10	62.0 (4)
N8—Ni2—O6—C29	−16.9 (5)	C23—C19—C20—N10	−60.5 (4)
O5—Ni2—O6—C29	−0.3 (2)	C18—C19—C20—N10	−178.2 (3)
N1—N2—C1—N3	−0.6 (5)	N10—N11—C21—N12	0.1 (6)
Ni1—N2—C1—N3	−169.4 (3)	Ni2ⁱⁱ—N11—C21—N12	171.4 (4)
C2—N3—C1—N2	0.7 (6)	C22—N12—C21—N11	−0.1 (7)
C1—N3—C2—N1	−0.5 (5)	C21—N12—C22—N10	0.1 (7)
N2—N1—C2—N3	0.1 (5)	N11—N10—C22—N12	0.0 (7)
C3—N1—C2—N3	179.6 (4)	C20—N10—C22—N12	177.1 (5)
C2—N1—C3—C4	−114.6 (5)	C7—N4—N5—C6	0.1 (4)
N2—N1—C3—C4	64.8 (5)	C5—N4—N5—C6	178.0 (4)
Ni1—O1—C4—C8	−113.7 (3)	C7—N4—N5—Ni1ⁱ	159.5 (3)
Ni1ⁱ—O1—C4—C8	101.1 (3)	C5—N4—N5—Ni1ⁱ	−22.6 (4)
Ni1—O1—C4—C3	7.8 (4)	C7—N4—C5—C4	−109.0 (5)
Ni1ⁱ—O1—C4—C3	−137.4 (3)	N5—N4—C5—C4	73.5 (4)
Ni1—O1—C4—C5	125.0 (3)	O1—C4—C5—N4	−46.4 (4)
Ni1ⁱ—O1—C4—C5	−20.2 (4)	C8—C4—C5—N4	−168.3 (3)
N1—C3—C4—O1	−62.6 (4)	C3—C4—C5—N4	72.7 (4)
N1—C3—C4—C8	59.4 (4)	N4—N5—C6—N6	−0.1 (5)
N1—C3—C4—C5	178.4 (3)	Ni1ⁱ—N5—C6—N6	−153.8 (3)
O1—C4—C8—C13	4.7 (5)	C7—N6—C6—N5	0.1 (6)
C3—C4—C8—C13	−116.9 (4)	N5—N4—C7—N6	0.0 (5)
C5—C4—C8—C13	125.9 (4)	C5—N4—C7—N6	−177.7 (4)
O1—C4—C8—C9	−177.0 (4)	C6—N6—C7—N4	0.0 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7···N9ⁱⁱⁱ	0.82	2.06	2.861 (11)	166

Symmetry code: (iii) x, y, z+1.

Experimental details

Crystal data
Chemical formula	[Ni₂(C₁₃H₁₁F₂N₆O)₂(C₂H₃O₂)₂]·0.5CH₄O
M_r	862.08
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	11.3898 (12), 12.4447 (14), 14.0012 (16)
α, β, γ (°)	65.211 (1), 86.815 (2), 88.100 (2)
V (Å³)	1798.8 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.13
Crystal size (mm)	0.42 × 0.37 × 0.35

Data collection
Diffractometer	Siemens SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.648, 0.693
No. of measured, independent and observed [I > 2σ(I)] reflections	9439, 6256, 4649
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.127, 0.97
No. of reflections	6256
No. of parameters	508
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.09, −0.30

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Ni1—O1	2.008 (3)	Ni2—O2	2.033 (3)
Ni1—O1ⁱ	2.053 (3)	Ni2—O2ⁱⁱ	2.030 (3)
Ni1—O3	2.050 (3)	Ni2—O5	2.112 (3)
Ni1—O4	2.202 (3)	Ni2—O6	2.108 (3)
Ni1—N2	2.085 (3)	Ni2—N8	2.089 (3)
Ni1—N5ⁱ	2.076 (3)	Ni2—N11ⁱⁱ	2.067 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7···N9ⁱⁱⁱ	0.82	2.06	2.861 (11)	166

Symmetry code: (iii) x, y, z+1.

Acknowledgements

This work was supported by the Innovation Project (gxun-chx2009080) of Guangxi University for Nationalities.

References

Agh-Atabay, N. M., Dulger, B. & Gucin, F. (2003). Eur. J. Med. Chem. 38, 875–881. Web of Science CrossRef PubMed CAS Google Scholar
Ali, M. A., Mirza, A. H., Nazimuddin, M., Dhar, P. K. & Butcher, R. J. (2002). Transition Met. Chem. 27, 27–33. Web of Science CSD CrossRef CAS Google Scholar
Castilo-Blum, S. E. & Barba-Behrens, N. (2000). Coord. Chem. Rev. 196, 3–30. Web of Science CrossRef Google Scholar
Goodman, J. L., Winston, D. J., Greenfield, R. A., Chandrasekar, P. H., Fox, B., Kaizer, H., Shadduck, R. K., Shea, T. C., Stiff, P. & Friedman, D. J. (1992). N. Engl. J. Med. 326, 845–851. CrossRef PubMed CAS Web of Science Google Scholar
Inoue, Y., Hoshino, M., Takahashi, H., Noguchi, T., Murata, T., Kanzaki, Y., Hamashima, H. & Sasatsu, M. (2002). J. Inorg. Biochem. 92, 37–42. Web of Science CrossRef PubMed CAS Google Scholar
Patel, R. N., Kumar, S. & Pandeya, K. B. (2002). J. Inorg. Biochem. 89, 61–68. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Tavman, A., Ülküseven, B. & Agh-Atabay, N. M. (2000). Transition Met. Chem. 25, 324–328. Web of Science CrossRef CAS Google Scholar

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