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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): m75–m76.
Published online 2009 December 19. doi:  10.1107/S160053680905377X
PMCID: PMC2980145

Bis[μ-2-(2,4-difluoro­phen­yl)-1,3-bis­(1,2,4-triazol-1-yl)propan-2-olato-κ4 N 2,O:O,N 2′]bis­[(acetato-κ2 O,O′)nickel(II)] methanol hemisolvate

Abstract

In the title complex, [Ni2(C13H11F2N6O)2(C2H3O2)2]·0.5CH3OH, there are two half-molecules in the asymmetric unit. The two centrosymmetrically related NiII atoms, each attached to an acetate ligand, are linked by two fluconazole ligands. Each NiII 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 [triangle]). For general background to inter­actions between metal ions and drugs, see: Agh-Atabay et al. (2003 [triangle]); Ali et al. (2002 [triangle]); Castilo-Blum & Barba-Behrens (2000 [triangle]); Inoue et al. (2002 [triangle]); Patel et al. (2002 [triangle]); Tavman et al. (2000 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-00m75-scheme1.jpg

Experimental

Crystal data

  • [Ni2(C13H11F2N6O)2(C2H3O2)2]·0.5CH4O
  • M r = 862.08
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-00m75-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.127
  • S = 0.97
  • 6256 reflections
  • 508 parameters
  • H-atom parameters constrained
  • Δρmax = 1.09 e Å−3
  • Δρmin = −0.30 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680905377X/hy2245sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

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 NiII ions, two fluconazole ligands, two bidentate coordinated acetate ligands and a half-occupied solvent methanol molecule. Each fluconazole ligand links the NiII centers via its deprotonated hydroxyl group and two triazole groups. The NiII 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.

Experimental

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 C30.5H30F4N12Ni2O6.5: C 42.48, N 19.50, H 3.48%; found: C 42.61, N 19.41, H 3.53%.

Refinement

H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 (aromatic), 0.97 (CH2) and 0.96 (CH3) Å and with Uiso(H) = 1.2(1.5 for methyl)Ueq(C). H atom bonded to O atom was found in difference Fourier map and refined as riding, with O—H = 0.82 Å and Uiso(H) = 1.5Ueq(O). The highest residual electron density was found 1.09 Å from O7 and the deepest hole 0.30 Å from C31.

Figures

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.

Crystal data

[Ni2(C13H11F2N6O)2(C2H3O2)2]·0.5CH4OZ = 2
Mr = 862.08F(000) = 882
Triclinic, P1Dx = 1.592 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.3898 (12) ÅCell parameters from 3550 reflections
b = 12.4447 (14) Åθ = 2.5–27.9°
c = 14.0012 (16) ŵ = 1.13 mm1
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

Siemens SMART 1000 CCD diffractometer6256 independent reflections
Radiation source: fine-focus sealed tube4649 reflections with I > 2σ(I)
graphiteRint = 0.018
[var phi] and ω scansθmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −13→11
Tmin = 0.648, Tmax = 0.693k = −13→14
9439 measured reflectionsl = −16→16

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H-atom parameters constrained
S = 0.97w = 1/[σ2(Fo2) + (0.058P)2 + 3.8657P] where P = (Fo2 + 2Fc2)/3
6256 reflections(Δ/σ)max = 0.001
508 parametersΔρmax = 1.09 e Å3
0 restraintsΔρmin = −0.30 e Å3

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

xyzUiso*/UeqOcc. (<1)
Ni1−0.01760 (4)−0.09636 (4)0.11391 (4)0.03078 (15)
Ni20.62054 (4)0.55904 (4)0.46306 (4)0.03113 (15)
F10.1595 (3)0.3241 (3)0.1388 (3)0.0802 (10)
F2−0.2181 (4)0.4782 (4)0.1417 (4)0.1098 (14)
F30.3015 (3)0.9504 (3)0.3828 (2)0.0719 (9)
F40.3922 (4)0.9592 (3)0.7008 (3)0.1012 (13)
N10.0516 (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)
N70.4966 (3)0.7223 (3)0.2737 (3)0.0348 (8)
N80.5773 (3)0.6318 (3)0.3051 (3)0.0372 (8)
N90.5101 (4)0.6616 (4)0.1477 (3)0.0507 (10)
O10.0197 (2)0.0766 (2)0.03910 (19)0.0294 (6)
O20.4526 (2)0.6025 (2)0.4913 (2)0.0311 (6)
O3−0.0020 (3)−0.2773 (3)0.1774 (2)0.0446 (7)
O40.1604 (3)−0.1751 (2)0.1378 (2)0.0421 (7)
O50.7026 (3)0.7080 (3)0.4645 (2)0.0421 (7)
O60.6725 (3)0.5479 (2)0.6091 (2)0.0401 (7)
O70.5255 (11)0.7012 (13)0.9308 (7)0.121 (4)0.50
H70.51190.69880.98970.181*0.50
C1−0.0878 (4)−0.1130 (4)0.3437 (3)0.0454 (11)
H1−0.1473−0.16820.36030.054*
C20.0249 (4)0.0102 (4)0.3538 (3)0.0470 (11)
H20.06250.05980.37660.056*
C30.1393 (4)0.0623 (4)0.1802 (3)0.0373 (10)
H3A0.18980.00410.16860.045*
H3B0.18790.10940.20250.045*
C40.0834 (3)0.1436 (3)0.0756 (3)0.0319 (9)
C80.0046 (4)0.2366 (4)0.0923 (3)0.0373 (10)
C90.0427 (4)0.3203 (4)0.1237 (4)0.0502 (12)
C10−0.0297 (5)0.4014 (5)0.1419 (5)0.0709 (17)
H10−0.00050.45590.16370.085*
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)
H12−0.27140.31820.08520.073*
C13−0.1144 (4)0.2385 (4)0.0785 (4)0.0444 (11)
H13−0.14440.18390.05720.053*
C140.1097 (4)−0.2731 (4)0.1687 (3)0.0409 (10)
C150.1762 (5)−0.3857 (4)0.1921 (4)0.0600 (14)
H15A0.1644−0.41230.13820.090*
H15B0.1485−0.44470.25910.090*
H15C0.2584−0.37270.19430.090*
C160.5812 (4)0.5993 (4)0.2270 (3)0.0443 (11)
H160.62930.53770.22640.053*
C170.4589 (4)0.7378 (4)0.1811 (3)0.0426 (10)
H170.40370.79480.14410.051*
C180.4701 (4)0.7880 (3)0.3375 (3)0.0353 (9)
H18A0.42570.85910.29700.042*
H18B0.54300.81180.35530.042*
C190.3983 (3)0.7124 (3)0.4401 (3)0.0325 (9)
C230.3932 (4)0.7800 (4)0.5102 (3)0.0370 (10)
C240.3472 (4)0.8938 (4)0.4802 (4)0.0489 (12)
C250.3445 (5)0.9556 (5)0.5418 (4)0.0638 (15)
H250.31271.03170.51880.077*
C260.3907 (5)0.8997 (5)0.6383 (5)0.0643 (15)
C270.4371 (5)0.7879 (5)0.6747 (4)0.0603 (14)
H270.46770.75200.74120.072*
C280.4374 (4)0.7296 (4)0.6095 (3)0.0461 (11)
H280.46860.65330.63370.055*
C290.7118 (4)0.6521 (4)0.5628 (4)0.0407 (10)
C300.7676 (5)0.7072 (5)0.6254 (4)0.0596 (14)
H30A0.82970.65650.66460.089*
H30B0.70960.71800.67320.089*
H30C0.79940.78270.57860.089*
C310.554 (2)0.585 (2)0.9393 (17)0.160 (9)0.50
H31A0.62790.55980.97160.240*0.50
H31B0.55880.58560.87030.240*0.50
H31C0.49360.53120.98160.240*0.50
N100.1984 (3)0.6289 (3)0.5011 (3)0.0421 (9)
N110.2213 (3)0.5129 (3)0.5628 (3)0.0390 (8)
N120.0551 (4)0.5703 (4)0.6210 (4)0.0704 (14)
C200.2747 (4)0.6961 (4)0.4094 (3)0.0409 (10)
H20A0.23940.77320.37030.049*
H20B0.28140.65520.36360.049*
C210.1330 (4)0.4827 (4)0.6329 (4)0.0519 (12)
H210.12500.40690.68640.062*
H220.06540.73410.50960.062*
C220.0994 (5)0.6589 (5)0.5386 (4)0.0637 (15)
N40.2486 (3)0.1225 (3)−0.0388 (3)0.0332 (8)
N50.1993 (3)0.0854 (3)−0.1060 (3)0.0377 (8)
N60.3799 (3)0.0060 (4)−0.0680 (3)0.0539 (10)
C50.1863 (4)0.2054 (4)−0.0048 (3)0.0359 (9)
H5A0.15560.2707−0.06550.043*
H5B0.24060.23730.02750.043*
C60.2825 (4)0.0161 (4)−0.1201 (4)0.0467 (11)
H60.2737−0.0229−0.16320.056*
C70.3550 (4)0.0744 (4)−0.0177 (4)0.0461 (11)
H7A0.40560.08680.02650.055*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ni10.0273 (3)0.0317 (3)0.0295 (3)−0.0020 (2)−0.0011 (2)−0.0089 (2)
Ni20.0284 (3)0.0302 (3)0.0311 (3)0.0001 (2)0.0014 (2)−0.0095 (2)
F10.056 (2)0.104 (3)0.123 (3)−0.0002 (17)−0.0196 (19)−0.088 (2)
F20.095 (3)0.112 (3)0.165 (4)0.031 (2)0.008 (3)−0.103 (3)
F30.094 (2)0.0541 (18)0.066 (2)0.0376 (17)−0.0221 (17)−0.0239 (16)
F40.161 (4)0.088 (3)0.084 (3)0.006 (2)0.010 (2)−0.067 (2)
N10.0351 (19)0.042 (2)0.0330 (19)−0.0058 (16)−0.0044 (15)−0.0137 (16)
N20.036 (2)0.043 (2)0.0312 (18)−0.0036 (16)−0.0030 (15)−0.0123 (16)
N30.056 (3)0.063 (3)0.039 (2)−0.008 (2)0.0062 (19)−0.022 (2)
N70.0362 (19)0.0324 (18)0.0304 (18)0.0010 (15)0.0033 (15)−0.0085 (15)
N80.037 (2)0.038 (2)0.0330 (19)0.0040 (16)0.0025 (15)−0.0121 (16)
N90.059 (3)0.054 (2)0.039 (2)0.004 (2)−0.0032 (19)−0.0193 (19)
O10.0304 (14)0.0292 (14)0.0286 (14)−0.0036 (11)−0.0009 (11)−0.0118 (11)
O20.0297 (14)0.0263 (14)0.0338 (15)0.0024 (11)0.0009 (11)−0.0094 (12)
O30.0375 (18)0.0379 (17)0.0458 (18)−0.0038 (13)−0.0062 (14)−0.0044 (14)
O40.0372 (17)0.0329 (16)0.0531 (18)−0.0034 (13)−0.0038 (14)−0.0146 (14)
O50.0420 (17)0.0402 (17)0.0379 (17)−0.0049 (13)−0.0026 (13)−0.0099 (14)
O60.0422 (17)0.0387 (17)0.0360 (16)0.0000 (13)−0.0043 (13)−0.0119 (13)
O70.147 (10)0.180 (12)0.052 (5)−0.008 (9)−0.021 (6)−0.062 (7)
C10.044 (3)0.052 (3)0.034 (2)−0.009 (2)0.002 (2)−0.012 (2)
C20.051 (3)0.052 (3)0.040 (3)−0.004 (2)−0.002 (2)−0.021 (2)
C30.029 (2)0.043 (2)0.037 (2)−0.0041 (18)−0.0032 (17)−0.0137 (19)
C40.029 (2)0.034 (2)0.035 (2)−0.0022 (17)−0.0012 (17)−0.0154 (18)
C80.036 (2)0.039 (2)0.039 (2)0.0019 (18)0.0000 (18)−0.018 (2)
C90.046 (3)0.058 (3)0.060 (3)−0.001 (2)−0.001 (2)−0.038 (3)
C100.074 (4)0.070 (4)0.096 (5)−0.001 (3)0.005 (3)−0.062 (4)
C110.067 (4)0.066 (4)0.089 (4)0.017 (3)0.010 (3)−0.050 (3)
C120.045 (3)0.063 (3)0.081 (4)0.010 (2)0.005 (3)−0.039 (3)
C130.037 (3)0.045 (3)0.055 (3)0.001 (2)0.002 (2)−0.026 (2)
C140.043 (3)0.037 (2)0.038 (2)0.006 (2)−0.0127 (19)−0.010 (2)
C150.058 (3)0.042 (3)0.078 (4)0.011 (2)−0.027 (3)−0.021 (3)
C160.052 (3)0.042 (3)0.040 (3)0.006 (2)0.005 (2)−0.019 (2)
C170.044 (3)0.045 (3)0.032 (2)0.006 (2)−0.0033 (19)−0.010 (2)
C180.038 (2)0.031 (2)0.033 (2)0.0030 (18)0.0007 (18)−0.0102 (18)
C190.032 (2)0.028 (2)0.034 (2)0.0037 (16)−0.0014 (17)−0.0104 (17)
C230.037 (2)0.037 (2)0.036 (2)0.0045 (18)0.0030 (18)−0.0158 (19)
C240.057 (3)0.044 (3)0.045 (3)0.012 (2)−0.002 (2)−0.018 (2)
C250.082 (4)0.046 (3)0.066 (4)0.015 (3)0.009 (3)−0.028 (3)
C260.083 (4)0.058 (3)0.065 (4)0.000 (3)0.016 (3)−0.042 (3)
C270.081 (4)0.059 (3)0.046 (3)0.005 (3)0.001 (3)−0.027 (3)
C280.054 (3)0.045 (3)0.040 (3)0.003 (2)0.003 (2)−0.020 (2)
C290.034 (2)0.041 (3)0.049 (3)0.0045 (19)−0.0088 (19)−0.020 (2)
C300.067 (4)0.056 (3)0.062 (3)0.000 (3)−0.018 (3)−0.029 (3)
C310.17 (2)0.19 (2)0.128 (17)−0.004 (18)−0.048 (15)−0.066 (17)
N100.033 (2)0.040 (2)0.045 (2)0.0059 (16)0.0001 (16)−0.0105 (17)
N110.0305 (19)0.037 (2)0.041 (2)0.0028 (15)0.0041 (15)−0.0082 (16)
N120.049 (3)0.065 (3)0.074 (3)0.013 (2)0.019 (2)−0.011 (2)
C200.040 (2)0.036 (2)0.035 (2)0.0034 (19)−0.0007 (19)−0.0040 (19)
C210.039 (3)0.050 (3)0.053 (3)0.001 (2)0.008 (2)−0.009 (2)
C220.045 (3)0.059 (3)0.071 (4)0.020 (3)0.006 (3)−0.013 (3)
N40.0221 (17)0.0383 (19)0.0385 (19)−0.0034 (14)−0.0008 (14)−0.0153 (16)
N50.0255 (18)0.047 (2)0.043 (2)−0.0037 (15)0.0036 (15)−0.0224 (17)
N60.032 (2)0.062 (3)0.072 (3)0.0084 (18)0.0005 (19)−0.033 (2)
C50.032 (2)0.036 (2)0.040 (2)−0.0021 (18)0.0008 (18)−0.0162 (19)
C60.035 (3)0.054 (3)0.057 (3)0.000 (2)0.008 (2)−0.031 (2)
C70.029 (2)0.054 (3)0.054 (3)−0.004 (2)−0.001 (2)−0.021 (2)

Geometric parameters (Å, °)

Ni1—O12.008 (3)C12—H120.9300
Ni1—O1i2.053 (3)C13—H130.9300
Ni1—O32.050 (3)C14—C151.489 (6)
Ni1—O42.202 (3)C15—H15A0.9600
Ni1—N22.085 (3)C15—H15B0.9600
Ni1—N5i2.076 (3)C15—H15C0.9600
Ni2—O22.033 (3)C16—H160.9300
Ni2—O2ii2.030 (3)C17—H170.9300
Ni2—O52.112 (3)C18—C191.552 (5)
Ni2—O62.108 (3)C18—H18A0.9700
Ni2—N82.089 (3)C18—H18B0.9700
Ni2—N11ii2.067 (3)C19—C231.535 (6)
F1—C91.364 (6)C19—C201.538 (6)
F2—C111.360 (6)C23—C281.381 (6)
F3—C241.368 (5)C23—C241.390 (6)
F4—C261.365 (6)C24—C251.375 (7)
N1—C21.335 (5)C25—C261.360 (8)
N1—N21.357 (5)C25—H250.9300
N1—C31.450 (5)C26—C271.365 (7)
N2—C11.325 (5)C27—C281.383 (6)
N3—C21.321 (6)C27—H270.9300
N3—C11.340 (6)C28—H280.9300
N7—C171.323 (5)C29—C301.497 (6)
N7—N81.367 (5)C30—H30A0.9600
N7—C181.457 (5)C30—H30B0.9600
N8—C161.314 (5)C30—H30C0.9600
N9—C171.328 (6)C31—H31A0.9600
N9—C161.351 (6)C31—H31B0.9600
O1—C41.387 (5)C31—H31C0.9600
O1—Ni1i2.053 (3)N10—C221.325 (6)
O2—C191.392 (4)N10—N111.361 (5)
O2—Ni2ii2.030 (3)N10—C201.459 (5)
O3—C141.272 (5)N11—C211.312 (5)
O4—C141.259 (5)N11—Ni2ii2.067 (3)
O5—C291.264 (5)N12—C221.307 (7)
O6—C291.266 (5)N12—C211.342 (6)
O7—C311.43 (2)C20—H20A0.9700
O7—H70.8200C20—H20B0.9700
C1—H10.9300C21—H210.9300
C2—H20.9300C22—H220.9300
C3—C41.547 (6)N4—C71.326 (5)
C3—H3A0.9700N4—N51.363 (5)
C3—H3B0.9700N4—C51.456 (5)
C4—C81.527 (6)N5—C61.322 (5)
C4—C51.556 (5)N5—Ni1i2.076 (3)
C8—C131.378 (6)N6—C71.329 (6)
C8—C91.380 (6)N6—C61.336 (6)
C9—C101.378 (7)C5—H5A0.9700
C10—C111.354 (8)C5—H5B0.9700
C10—H100.9300C6—H60.9300
C11—C121.360 (8)C7—H7A0.9300
C12—C131.389 (6)
O1—Ni1—O3162.20 (11)C14—C15—H15B109.5
O1—Ni1—O1i80.59 (11)H15A—C15—H15B109.5
O3—Ni1—O1i95.01 (11)C14—C15—H15C109.5
O1—Ni1—N5i99.07 (12)H15A—C15—H15C109.5
O3—Ni1—N5i97.64 (13)H15B—C15—H15C109.5
O1i—Ni1—N5i84.42 (12)N8—C16—N9115.2 (4)
O1—Ni1—N288.33 (12)N8—C16—H16122.4
O3—Ni1—N296.80 (13)N9—C16—H16122.4
O1i—Ni1—N2168.17 (12)N7—C17—N9111.2 (4)
N5i—Ni1—N293.32 (14)N7—C17—H17124.4
O1—Ni1—O4101.03 (10)N9—C17—H17124.4
O3—Ni1—O461.87 (11)N7—C18—C19111.4 (3)
O1i—Ni1—O493.99 (11)N7—C18—H18A109.4
N5i—Ni1—O4159.30 (12)C19—C18—H18A109.4
N2—Ni1—O492.17 (13)N7—C18—H18B109.4
O2ii—Ni2—O281.69 (11)C19—C18—H18B109.4
O2ii—Ni2—N11ii88.38 (12)H18A—C18—H18B108.0
O2—Ni2—N11ii169.91 (12)O2—C19—C23110.3 (3)
O2ii—Ni2—N898.46 (12)O2—C19—C20109.8 (3)
O2—Ni2—N885.09 (12)C23—C19—C20111.4 (3)
N11ii—Ni2—N894.62 (14)O2—C19—C18110.0 (3)
O2ii—Ni2—O6100.48 (11)C23—C19—C18107.5 (3)
O2—Ni2—O691.88 (11)C20—C19—C18107.8 (3)
N11ii—Ni2—O691.72 (13)C28—C23—C24115.2 (4)
N8—Ni2—O6160.18 (13)C28—C23—C19120.6 (4)
O2ii—Ni2—O5162.83 (11)C24—C23—C19124.2 (4)
O2—Ni2—O597.31 (11)F3—C24—C25116.6 (4)
N11ii—Ni2—O592.72 (13)F3—C24—C23119.0 (4)
N8—Ni2—O598.53 (12)C25—C24—C23124.4 (5)
O6—Ni2—O562.37 (11)C26—C25—C24116.5 (5)
C2—N1—N2108.4 (3)C26—C25—H25121.7
C2—N1—C3130.6 (4)C24—C25—H25121.7
N2—N1—C3120.9 (3)C25—C26—C27123.2 (5)
C1—N2—N1103.3 (3)C25—C26—F4118.3 (5)
C1—N2—Ni1137.8 (3)C27—C26—F4118.5 (5)
N1—N2—Ni1118.1 (2)C26—C27—C28117.9 (5)
C2—N3—C1103.2 (4)C26—C27—H27121.1
C17—N7—N8109.0 (3)C28—C27—H27121.1
C17—N7—C18130.7 (4)C23—C28—C27122.8 (5)
N8—N7—C18120.2 (3)C23—C28—H28118.6
C16—N8—N7102.5 (3)C27—C28—H28118.6
C16—N8—Ni2137.4 (3)O5—C29—O6119.4 (4)
N7—N8—Ni2117.4 (2)O5—C29—C30121.1 (4)
C17—N9—C16102.1 (4)O6—C29—C30119.5 (4)
C4—O1—Ni1127.5 (2)C29—C30—H30A109.5
C4—O1—Ni1i126.3 (2)C29—C30—H30B109.5
Ni1—O1—Ni1i99.41 (11)H30A—C30—H30B109.5
C19—O2—Ni2ii127.2 (2)C29—C30—H30C109.5
C19—O2—Ni2126.1 (2)H30A—C30—H30C109.5
Ni2ii—O2—Ni298.31 (11)H30B—C30—H30C109.5
C14—O3—Ni192.3 (2)O7—C31—H31A109.5
C14—O4—Ni185.8 (3)O7—C31—H31B109.5
C29—O5—Ni289.0 (3)H31A—C31—H31B109.5
C29—O6—Ni289.2 (2)O7—C31—H31C109.5
C31—O7—H7109.5H31A—C31—H31C109.5
N2—C1—N3114.2 (4)H31B—C31—H31C109.5
N2—C1—H1122.9C22—N10—N11107.8 (4)
N3—C1—H1122.9C22—N10—C20131.2 (4)
N3—C2—N1110.9 (4)N11—N10—C20120.9 (3)
N3—C2—H2124.5C21—N11—N10103.2 (3)
N1—C2—H2124.5C21—N11—Ni2ii138.1 (3)
N1—C3—C4112.3 (3)N10—N11—Ni2ii118.2 (2)
N1—C3—H3A109.2C22—N12—C21102.5 (4)
C4—C3—H3A109.2N10—C20—C19112.2 (3)
N1—C3—H3B109.2N10—C20—H20A109.2
C4—C3—H3B109.2C19—C20—H20A109.2
H3A—C3—H3B107.9N10—C20—H20B109.2
O1—C4—C8110.7 (3)C19—C20—H20B109.2
O1—C4—C3109.9 (3)H20A—C20—H20B107.9
C8—C4—C3109.8 (3)N11—C21—N12114.5 (4)
O1—C4—C5109.7 (3)N11—C21—H21122.7
C8—C4—C5109.8 (3)N12—C21—H21122.7
C3—C4—C5106.8 (3)N12—C22—N10112.0 (4)
C13—C8—C9115.3 (4)N12—C22—H22124.0
C13—C8—C4119.8 (4)N10—C22—H22124.0
C9—C8—C4124.8 (4)C7—N4—N5108.8 (3)
F1—C9—C10116.9 (4)C7—N4—C5130.5 (4)
F1—C9—C8118.7 (4)N5—N4—C5120.7 (3)
C10—C9—C8124.4 (5)C6—N5—N4102.5 (3)
C11—C10—C9116.5 (5)C6—N5—Ni1i135.2 (3)
C11—C10—H10121.7N4—N5—Ni1i117.6 (2)
C9—C10—H10121.7C7—N6—C6102.4 (4)
C10—C11—C12123.4 (5)N4—C5—C4111.0 (3)
C10—C11—F2117.5 (5)N4—C5—H5A109.4
C12—C11—F2119.1 (6)C4—C5—H5A109.4
C11—C12—C13117.5 (5)N4—C5—H5B109.4
C11—C12—H12121.2C4—C5—H5B109.4
C13—C12—H12121.2H5A—C5—H5B108.0
C8—C13—C12122.8 (5)N5—C6—N6115.2 (4)
C8—C13—H13118.6N5—C6—H6122.4
C12—C13—H13118.6N6—C6—H6122.4
O4—C14—O3119.8 (4)N4—C7—N6111.1 (4)
O4—C14—C15122.1 (4)N4—C7—H7A124.5
O3—C14—C15118.1 (4)N6—C7—H7A124.5
C14—C15—H15A109.5
C2—N1—N2—C10.3 (5)C3—C4—C8—C961.4 (5)
C3—N1—N2—C1−179.3 (4)C5—C4—C8—C9−55.8 (6)
C2—N1—N2—Ni1171.8 (3)C13—C8—C9—F1−179.8 (4)
C3—N1—N2—Ni1−7.7 (5)C4—C8—C9—F11.8 (7)
O1—Ni1—N2—C1135.6 (5)C13—C8—C9—C100.6 (8)
O3—Ni1—N2—C1−61.5 (5)C4—C8—C9—C10−177.8 (5)
O1i—Ni1—N2—C1115.2 (6)F1—C9—C10—C11179.7 (5)
N5i—Ni1—N2—C136.6 (5)C8—C9—C10—C11−0.7 (9)
O4—Ni1—N2—C1−123.4 (5)C9—C10—C11—C120.5 (10)
O1—Ni1—N2—N1−32.0 (3)C9—C10—C11—F2−178.8 (5)
O3—Ni1—N2—N1130.9 (3)C10—C11—C12—C13−0.2 (10)
O1i—Ni1—N2—N1−52.5 (7)F2—C11—C12—C13179.1 (5)
N5i—Ni1—N2—N1−131.0 (3)C9—C8—C13—C12−0.2 (7)
O4—Ni1—N2—N168.9 (3)C4—C8—C13—C12178.3 (4)
C17—N7—N8—C16−0.3 (4)C11—C12—C13—C80.0 (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—C15172.7 (4)
C18—N7—N8—Ni218.3 (4)Ni1—O3—C14—O45.3 (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—N90.3 (5)
N11ii—Ni2—N8—C1643.2 (5)Ni2—N8—C16—N9160.0 (3)
O6—Ni2—N8—C16151.4 (4)C17—N9—C16—N8−0.2 (5)
O5—Ni2—N8—C16136.6 (4)N8—N7—C17—N90.2 (5)
O2ii—Ni2—N8—N7111.7 (3)C18—N7—C17—N9176.5 (4)
O2—Ni2—N8—N730.9 (3)C16—N9—C17—N70.0 (5)
N11ii—Ni2—N8—N7−159.3 (3)C17—N7—C18—C19112.1 (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—C23116.3 (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—C4125.0 (3)Ni2—O2—C19—C20134.2 (3)
N2—Ni1—O1—C431.9 (3)Ni2ii—O2—C19—C18−125.3 (3)
O4—Ni1—O1—C4−60.0 (3)Ni2—O2—C19—C1815.7 (4)
O3—Ni1—O1—Ni1i76.9 (4)N7—C18—C19—O250.3 (4)
O1i—Ni1—O1—Ni1i0.0N7—C18—C19—C23170.4 (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—Ni1i92.27 (12)C20—C19—C23—C28121.3 (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—C24178.1 (4)
N8—Ni2—O2—C19−50.3 (3)C20—C19—C23—C24−59.6 (5)
O6—Ni2—O2—C19110.1 (3)C18—C19—C23—C2458.2 (5)
O5—Ni2—O2—C1947.7 (3)C28—C23—C24—F3−180.0 (4)
O2ii—Ni2—O2—Ni2ii0.0C19—C23—C24—F30.9 (7)
N11ii—Ni2—O2—Ni2ii10.5 (7)C28—C23—C24—C250.4 (7)
N8—Ni2—O2—Ni2ii99.31 (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—C260.1 (8)
O1—Ni1—O3—C1414.2 (5)C24—C25—C26—C27−0.5 (9)
O1i—Ni1—O3—C1488.9 (3)C24—C25—C26—F4178.4 (5)
N5i—Ni1—O3—C14173.9 (3)C25—C26—C27—C280.3 (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—C27178.6 (4)
O3—Ni1—O4—C143.0 (2)C26—C27—C28—C230.2 (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—C30179.8 (4)
N2—Ni1—O4—C1499.6 (3)Ni2—O6—C29—O50.6 (4)
O2ii—Ni2—O5—C293.1 (5)Ni2—O6—C29—C30−179.8 (4)
O2—Ni2—O5—C2988.6 (2)C22—N10—N11—C210.0 (5)
N11ii—Ni2—O5—C29−90.2 (3)C20—N10—N11—C21−177.5 (4)
N8—Ni2—O5—C29174.7 (3)C22—N10—N11—Ni2ii−173.4 (4)
O6—Ni2—O5—C290.3 (2)C20—N10—N11—Ni2ii9.0 (5)
O2ii—Ni2—O6—C29−179.5 (2)C22—N10—C20—C19116.9 (6)
O2—Ni2—O6—C29−97.6 (2)N11—N10—C20—C19−66.2 (5)
N11ii—Ni2—O6—C2991.8 (3)O2—C19—C20—N1062.0 (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—N120.1 (6)
Ni1—N2—C1—N3−169.4 (3)Ni2ii—N11—C21—N12171.4 (4)
C2—N3—C1—N20.7 (6)C22—N12—C21—N11−0.1 (7)
C1—N3—C2—N1−0.5 (5)C21—N12—C22—N100.1 (7)
N2—N1—C2—N30.1 (5)N11—N10—C22—N120.0 (7)
C3—N1—C2—N3179.6 (4)C20—N10—C22—N12177.1 (5)
C2—N1—C3—C4−114.6 (5)C7—N4—N5—C60.1 (4)
N2—N1—C3—C464.8 (5)C5—N4—N5—C6178.0 (4)
Ni1—O1—C4—C8−113.7 (3)C7—N4—N5—Ni1i159.5 (3)
Ni1i—O1—C4—C8101.1 (3)C5—N4—N5—Ni1i−22.6 (4)
Ni1—O1—C4—C37.8 (4)C7—N4—C5—C4−109.0 (5)
Ni1i—O1—C4—C3−137.4 (3)N5—N4—C5—C473.5 (4)
Ni1—O1—C4—C5125.0 (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—N472.7 (4)
N1—C3—C4—C859.4 (4)N4—N5—C6—N6−0.1 (5)
N1—C3—C4—C5178.4 (3)Ni1i—N5—C6—N6−153.8 (3)
O1—C4—C8—C134.7 (5)C7—N6—C6—N50.1 (6)
C3—C4—C8—C13−116.9 (4)N5—N4—C7—N60.0 (5)
C5—C4—C8—C13125.9 (4)C5—N4—C7—N6−177.7 (4)
O1—C4—C8—C9−177.0 (4)C6—N6—C7—N40.0 (5)

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

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O7—H7···N9iii0.822.062.861 (11)166

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2245).

References

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