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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): m967.
Published online 2010 July 17. doi:  10.1107/S160053681002773X
PMCID: PMC3007574

Bis[2,6-bis­(1H-benzimidazol-2-yl)pyridine]­nickel(II) dipicrate dimethyl­formamide disolvate

Abstract

In the title compound, [Ni(C19H13N5)2](C6H2N3O7)2·2C3H7NO, the NiII ion is coordinated by two tridentate 2,6-bis­(1H-benzimidazol-2-yl)pyridine ligands in a distorted octa­hedral geometry. In the crystal structure, the picrate anions and solvent dimethyl­formamide (DMF) mol­ecules are connected to the cation via inter­molecular N—H(...)O hydrogen bonds. Further stabilization is provided by weak inter­molecular C—H(...)O hydrogen bonds. One of the DMF moleclues is disordered over two sites with refined occupancies of 0.737 (3) and 0.263 (3).

Related literature

For a related structure, see: Freire et al. (2003 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m967-scheme1.jpg

Experimental

Crystal data

  • [Ni(C19H13N5)2](C6H2N3O7)2·2C3H7NO
  • M r = 1283.80
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m967-efi1.jpg
  • a = 14.2087 (3) Å
  • b = 26.5215 (5) Å
  • c = 14.6989 (3) Å
  • β = 93.775 (1)°
  • V = 5527.06 (19) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.44 mm−1
  • T = 153 K
  • 0.36 × 0.25 × 0.19 mm

Data collection

  • Rigaku R-AXIS Spider diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.857, T max = 0.921
  • 52251 measured reflections
  • 12544 independent reflections
  • 9403 reflections with I > 2σ(I)
  • R int = 0.038

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.106
  • S = 1.11
  • 12544 reflections
  • 814 parameters
  • 16 restraints
  • H-atom parameters constrained
  • Δρmax = 0.72 e Å−3
  • Δρmin = −0.60 e Å−3

Data collection: RAPID-AUTO (Rigaku/MSC (2004 [triangle]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681002773X/lh5079sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681002773X/lh5079Isup2.hkl

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

Acknowledgments

The authors acknowledge financial support and a grant from the ‘Qing Lan’ Talent Engineering Funds and Students’ Science and Technology Innovation Funds (grant No. DXS2010–040) of Lanzhou Jiaotong University. A grant from the Middle-Young Age Science Foundation (grant No. 3YS061-A25–023) and Long Yuan ‘Qing Nian’ of Gansu Province is also acknowledged.

supplementary crystallographic information

Comment

The asymmetric unit of the title complex (Fig. 1) consists of a [NiII(bbp)2] cations (bbp = 2,6-bis(1H-benzimidazol-2-yl)pyridine) two picrate anions, and two DMF solvate molecules. The NiII ion is coordinated by two tridentate bbp ligands in a distorted octahedral geometry. The Ni-N bond distances are comparable to those in a related structure Freire et al. (2003).

In the crystal structure, the picrate anions and solvent dimethylformamide (DMF) molecules are connected to the cation via intermolecular N-H···O hydrogen bonds (Fig. 2). One of the DMF moleclues is disordered over two sites with refined occupancies of 0.737 (3) and 0.263 (3).

Experimental

To a stirred solution of 2,6-bis(2-benzimidazolyl)pyridine (0.1557 g, 0.50 mmol) in hot MeOH (10 ml), Ni(picrate)2 (0.1287 g, 0.25 mmol) solution dissolved in MeOH (5 ml) was added. Owing to the formation of [NiII(bbp)2] complex, the pale yellow precipitate was generated immediately. The sediment was filtered, washed with MeOH and absolute Et2O, and dried in vacuo. The dried precipitate was dissolved in DMF to form a yellow solution that was allowed to evaporate at room temperature. The dried precipitate was dissolved in DMF and yellow crystals suitable for X-ray diffraction studies were obtained by ether diffusion into this solution after several days at room temperature (found: C, 52.25; H, 2.74; N, 20.15. Calcd. for C56 H44 N18 O16 Ni: C, 52.79; H, 2.64; N, 19.70).

Refinement

All H atoms were found in difference Fourier maps and were subsequently refined in a riding-model approximation with C—H = 0.95-0.98; N-H = 0.88Å and Uiso(H) = 1.2 Ueq(C,N) or 1.5 Ueq(Cmethyl).

Figures

Fig. 1.
The cation of the title compound with displacement ellipsoids drawn at the 30% probability level. H atoms bonded to C atoms have been omitted for clarity.
Fig. 2.
Part of the crystal structure of the title compound with hydrogen bonds drawn as dashed lines. The disorder is not shown.

Crystal data

[Ni(C19H13N5)2](C6H2N3O7)2·2C3H7NOF(000) = 2648
Mr = 1283.80Dx = 1.543 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 12544 reflections
a = 14.2087 (3) Åθ = 3.0–27.5°
b = 26.5215 (5) ŵ = 0.44 mm1
c = 14.6989 (3) ÅT = 153 K
β = 93.775 (1)°Block, yellow
V = 5527.06 (19) Å30.36 × 0.25 × 0.19 mm
Z = 4

Data collection

Rigaku R-AXIS Spider diffractometer12544 independent reflections
Radiation source: fine-focus sealed tube9403 reflections with I > 2σ(I)
graphiteRint = 0.038
ω scansθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −18→18
Tmin = 0.857, Tmax = 0.921k = −34→32
52251 measured reflectionsl = −18→19

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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.11w = 1/[σ2(Fo2) + (0.0471P)2 + 2.435P] where P = (Fo2 + 2Fc2)/3
12544 reflections(Δ/σ)max = 0.002
814 parametersΔρmax = 0.72 e Å3
16 restraintsΔρmin = −0.60 e Å3

Special details

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)

xyzUiso*/UeqOcc. (<1)
Ni0.952407 (18)0.808293 (9)0.021698 (16)0.01830 (7)
N10.81300 (12)0.82406 (6)−0.02938 (11)0.0216 (3)
N20.68026 (13)0.86678 (7)−0.00986 (12)0.0297 (4)
H2B0.63860.88530.01670.036*
N30.90743 (12)0.86064 (6)0.11151 (10)0.0198 (3)
N41.07615 (12)0.82338 (6)0.10559 (10)0.0196 (3)
N51.14391 (12)0.87962 (6)0.20267 (11)0.0237 (4)
H5B1.14950.90360.24400.028*
N60.91013 (12)0.74464 (6)0.09522 (10)0.0192 (3)
N70.90002 (12)0.66063 (6)0.10016 (10)0.0196 (3)
H7A0.90420.62890.08330.024*
N80.98180 (12)0.74986 (6)−0.06205 (10)0.0192 (3)
N91.01771 (12)0.84446 (6)−0.08505 (11)0.0222 (4)
N101.08396 (13)0.83546 (7)−0.21762 (11)0.0266 (4)
H10B1.10240.8212−0.26750.032*
C10.75258 (15)0.81827 (8)−0.10674 (13)0.0235 (4)
C20.76573 (15)0.79269 (8)−0.18759 (14)0.0266 (4)
H2A0.82090.7733−0.19490.032*
C30.69571 (17)0.79652 (9)−0.25670 (14)0.0323 (5)
H3A0.70300.7796−0.31280.039*
C40.61400 (17)0.82489 (10)−0.24579 (15)0.0377 (6)
H4A0.56760.8271−0.29520.045*
C50.59884 (17)0.84959 (10)−0.16568 (16)0.0393 (6)
H5A0.54290.8684−0.15830.047*
C60.66955 (16)0.84560 (9)−0.09641 (14)0.0286 (5)
C70.76675 (14)0.85343 (8)0.02569 (13)0.0225 (4)
C80.81559 (15)0.87180 (7)0.11020 (13)0.0217 (4)
C90.77778 (15)0.89747 (8)0.18153 (13)0.0241 (4)
H9A0.71230.90480.18080.029*
C100.83956 (15)0.91218 (7)0.25447 (13)0.0242 (4)
H10A0.81550.92900.30510.029*
C110.93499 (15)0.90269 (7)0.25414 (13)0.0233 (4)
H11A0.97750.91390.30250.028*
C120.96725 (14)0.87593 (7)0.18021 (12)0.0200 (4)
C131.06310 (14)0.85976 (7)0.16579 (12)0.0200 (4)
C141.21635 (15)0.85501 (7)0.16295 (13)0.0228 (4)
C151.31347 (16)0.86088 (8)0.17293 (14)0.0294 (5)
H15A1.34230.88530.21310.035*
C161.36581 (16)0.82949 (9)0.12155 (14)0.0293 (5)
H16A1.43260.83250.12610.035*
C171.32360 (16)0.79310 (8)0.06248 (13)0.0260 (4)
H17A1.36260.77180.02920.031*
C181.22709 (15)0.78752 (7)0.05159 (13)0.0229 (4)
H18A1.19880.76300.01140.027*
C191.17274 (14)0.81968 (7)0.10238 (12)0.0202 (4)
C200.87517 (14)0.73085 (7)0.17740 (12)0.0202 (4)
C210.84671 (15)0.76066 (8)0.24916 (13)0.0242 (4)
H21A0.85050.79640.24700.029*
C220.81314 (16)0.73620 (8)0.32282 (13)0.0258 (4)
H22A0.79280.75550.37230.031*
C230.80823 (15)0.68362 (8)0.32654 (13)0.0258 (4)
H23A0.78500.66810.37880.031*
C240.83610 (15)0.65352 (8)0.25659 (13)0.0238 (4)
H24A0.83300.61780.25960.029*
C250.86886 (14)0.67821 (7)0.18163 (12)0.0195 (4)
C260.92275 (14)0.70159 (7)0.05158 (12)0.0190 (4)
C270.95905 (14)0.70291 (7)−0.03946 (12)0.0198 (4)
C280.97005 (15)0.66250 (7)−0.09852 (13)0.0223 (4)
H28A0.95250.6292−0.08260.027*
C291.00753 (15)0.67264 (8)−0.18119 (13)0.0256 (4)
H29A1.01660.6458−0.22250.031*
C301.03200 (15)0.72131 (8)−0.20469 (13)0.0258 (4)
H30A1.05790.7283−0.26130.031*
C311.01730 (14)0.75933 (7)−0.14277 (12)0.0212 (4)
C321.03792 (14)0.81305 (8)−0.15124 (12)0.0222 (4)
C331.09654 (15)0.88502 (8)−0.19215 (15)0.0278 (5)
C341.14196 (19)0.92483 (9)−0.23244 (19)0.0431 (6)
H34A1.16750.9217−0.29030.052*
C351.1477 (2)0.96901 (9)−0.1837 (2)0.0539 (8)
H35A1.17970.9968−0.20810.065*
C361.10840 (19)0.97476 (9)−0.0996 (2)0.0457 (7)
H36A1.11471.0061−0.06850.055*
C371.06076 (16)0.93587 (8)−0.06091 (16)0.0321 (5)
H37A1.03280.9399−0.00440.038*
C381.05538 (15)0.89021 (8)−0.10836 (14)0.0253 (4)
O10.65289 (12)0.54468 (5)0.82415 (10)0.0306 (3)
O20.62027 (14)0.51404 (6)0.64861 (10)0.0410 (4)
O30.67343 (13)0.43908 (6)0.62613 (10)0.0400 (4)
O40.59111 (12)0.31139 (6)0.84018 (11)0.0351 (4)
O50.59714 (13)0.33068 (6)0.98397 (11)0.0403 (4)
O60.64921 (15)0.50176 (7)1.07987 (11)0.0502 (5)
O70.58363 (14)0.55750 (6)0.98960 (12)0.0450 (4)
N110.64320 (14)0.47168 (7)0.67589 (12)0.0294 (4)
N120.59939 (13)0.34216 (7)0.90252 (13)0.0292 (4)
N130.61788 (13)0.51554 (7)1.00389 (12)0.0306 (4)
C390.63458 (15)0.49941 (8)0.83836 (14)0.0240 (4)
C400.63181 (15)0.45938 (8)0.77095 (13)0.0241 (4)
C410.62234 (15)0.40924 (8)0.79094 (14)0.0251 (4)
H41A0.62320.38460.74410.030*
C420.61151 (15)0.39492 (8)0.88062 (14)0.0251 (4)
C430.61092 (15)0.43016 (8)0.94946 (14)0.0259 (4)
H43A0.60430.41991.01060.031*
C440.62006 (14)0.48017 (8)0.92860 (13)0.0240 (4)
O80.88901 (12)0.57028 (5)0.00568 (9)0.0300 (3)
O90.92480 (11)0.55055 (5)−0.16937 (10)0.0294 (3)
O100.84170 (12)0.48845 (6)−0.22604 (10)0.0347 (4)
O110.82471 (14)0.33880 (6)−0.04445 (12)0.0456 (5)
O120.79563 (12)0.34836 (6)0.09758 (11)0.0395 (4)
O130.86025 (13)0.50378 (7)0.24763 (10)0.0408 (4)
O140.94923 (12)0.55764 (6)0.18430 (10)0.0336 (4)
N140.87920 (12)0.51166 (6)−0.16065 (11)0.0234 (4)
N150.81975 (14)0.36483 (7)0.02401 (13)0.0314 (4)
N160.89668 (13)0.52102 (7)0.18029 (11)0.0259 (4)
C450.88191 (14)0.52360 (7)0.00939 (13)0.0210 (4)
C460.87130 (14)0.49064 (7)−0.06978 (13)0.0207 (4)
C470.85235 (14)0.44015 (8)−0.06581 (14)0.0231 (4)
H47A0.84540.4207−0.12010.028*
C480.84342 (15)0.41773 (7)0.01854 (14)0.0244 (4)
C490.85692 (14)0.44525 (8)0.09820 (14)0.0234 (4)
H49A0.85150.42940.15560.028*
C500.87808 (14)0.49524 (7)0.09376 (13)0.0211 (4)
O161.05337 (12)0.58190 (7)0.59231 (12)0.0446 (4)
N180.91649 (14)0.54522 (7)0.53721 (12)0.0309 (4)
C540.9070 (3)0.57566 (11)0.45561 (18)0.0589 (9)
H54A0.94700.60560.46350.088*
H54B0.84110.58600.44430.088*
H54C0.92650.55600.40370.088*
C550.8405 (2)0.50987 (11)0.55095 (17)0.0467 (7)
H55A0.85610.48990.60600.070*
H55B0.83220.48740.49810.070*
H55C0.78190.52850.55800.070*
C560.98743 (17)0.55163 (9)0.59809 (15)0.0341 (5)
H560.98830.53130.65130.041*
O150.6423 (2)0.71003 (13)1.12342 (16)0.0494 (4)0.737 (3)
N170.6175 (3)0.70137 (18)0.97022 (17)0.0494 (4)0.737 (3)
C510.6925 (2)0.66572 (14)0.9597 (2)0.0494 (4)0.737 (3)
H51A0.72820.66101.01840.074*0.737 (3)
H51B0.73460.67850.91490.074*0.737 (3)
H51C0.66570.63340.93870.074*0.737 (3)
C520.5575 (3)0.71317 (16)0.8899 (2)0.0494 (4)0.737 (3)
H52A0.51010.73800.90540.074*0.737 (3)
H52B0.52590.68240.86690.074*0.737 (3)
H52C0.59580.72710.84280.074*0.737 (3)
C530.5989 (2)0.71974 (15)1.0503 (2)0.0494 (4)0.737 (3)
H530.54730.74251.05180.059*0.737 (3)
O15'0.6142 (6)0.7010 (4)1.1271 (4)0.0494 (4)0.263 (3)
N17'0.6367 (8)0.6933 (4)0.9769 (3)0.0494 (4)0.263 (3)
C51'0.6808 (7)0.6646 (4)0.9079 (5)0.0494 (4)0.263 (3)
H51D0.71960.63780.93710.074*0.263 (3)
H51E0.72080.68690.87380.074*0.263 (3)
H51F0.63210.64960.86610.074*0.263 (3)
C52'0.5766 (6)0.7345 (3)0.9489 (5)0.0494 (4)0.263 (3)
H52D0.55080.74991.00260.074*0.263 (3)
H52E0.52480.72220.90750.074*0.263 (3)
H52F0.61300.75980.91740.074*0.263 (3)
C53'0.6509 (6)0.6804 (3)1.0640 (4)0.0494 (4)0.263 (3)
H53'0.69250.65311.07820.059*0.263 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ni0.02219 (14)0.01680 (13)0.01589 (12)−0.00195 (10)0.00117 (9)−0.00103 (9)
N10.0220 (9)0.0225 (8)0.0201 (8)0.0003 (7)0.0004 (6)−0.0026 (7)
N20.0236 (10)0.0395 (11)0.0256 (9)0.0061 (8)−0.0004 (7)−0.0083 (8)
N30.0248 (9)0.0162 (8)0.0183 (8)−0.0010 (7)0.0005 (6)−0.0004 (6)
N40.0239 (9)0.0162 (8)0.0184 (8)−0.0018 (7)−0.0016 (6)−0.0010 (6)
N50.0253 (10)0.0207 (9)0.0246 (9)0.0006 (7)−0.0030 (7)−0.0077 (7)
N60.0230 (9)0.0182 (8)0.0165 (8)−0.0023 (7)0.0027 (6)−0.0008 (6)
N70.0248 (9)0.0163 (8)0.0180 (8)−0.0013 (7)0.0035 (6)−0.0023 (6)
N80.0220 (9)0.0202 (8)0.0156 (7)−0.0029 (7)0.0014 (6)−0.0013 (6)
N90.0251 (9)0.0206 (8)0.0206 (8)−0.0026 (7)0.0000 (7)0.0022 (7)
N100.0286 (10)0.0312 (10)0.0205 (8)−0.0002 (8)0.0047 (7)0.0069 (7)
C10.0228 (11)0.0266 (11)0.0210 (9)−0.0021 (8)−0.0006 (8)−0.0032 (8)
C20.0249 (11)0.0306 (11)0.0243 (10)0.0008 (9)0.0007 (8)−0.0033 (9)
C30.0325 (13)0.0413 (13)0.0227 (10)−0.0031 (10)−0.0012 (9)−0.0092 (9)
C40.0284 (13)0.0565 (16)0.0270 (11)0.0029 (11)−0.0071 (9)−0.0090 (11)
C50.0255 (12)0.0571 (16)0.0346 (12)0.0092 (11)−0.0039 (10)−0.0099 (11)
C60.0249 (11)0.0366 (12)0.0239 (10)0.0005 (9)−0.0012 (8)−0.0076 (9)
C70.0216 (11)0.0240 (10)0.0219 (10)−0.0005 (8)0.0018 (8)−0.0005 (8)
C80.0251 (11)0.0189 (10)0.0211 (9)−0.0008 (8)0.0021 (8)0.0011 (8)
C90.0240 (11)0.0235 (10)0.0252 (10)−0.0009 (8)0.0033 (8)−0.0010 (8)
C100.0311 (12)0.0217 (10)0.0201 (9)−0.0003 (9)0.0046 (8)−0.0029 (8)
C110.0290 (12)0.0208 (10)0.0200 (9)−0.0010 (8)−0.0005 (8)−0.0021 (8)
C120.0247 (11)0.0164 (9)0.0188 (9)−0.0005 (8)−0.0008 (7)0.0004 (7)
C130.0258 (11)0.0169 (9)0.0169 (9)0.0003 (8)−0.0015 (7)−0.0007 (7)
C140.0261 (11)0.0191 (10)0.0226 (10)−0.0002 (8)−0.0025 (8)−0.0012 (8)
C150.0278 (12)0.0302 (11)0.0294 (11)−0.0014 (9)−0.0051 (9)−0.0067 (9)
C160.0226 (11)0.0379 (12)0.0268 (11)0.0017 (9)−0.0026 (8)0.0019 (9)
C170.0301 (12)0.0280 (11)0.0202 (10)0.0045 (9)0.0034 (8)0.0021 (8)
C180.0308 (12)0.0210 (10)0.0169 (9)−0.0007 (8)0.0015 (8)0.0005 (8)
C190.0250 (11)0.0170 (9)0.0184 (9)−0.0002 (8)−0.0012 (7)0.0018 (7)
C200.0209 (10)0.0205 (10)0.0192 (9)−0.0020 (8)0.0014 (7)0.0006 (8)
C210.0330 (12)0.0205 (10)0.0191 (9)−0.0010 (9)0.0021 (8)−0.0028 (8)
C220.0325 (12)0.0262 (11)0.0192 (10)0.0029 (9)0.0053 (8)−0.0012 (8)
C230.0306 (12)0.0270 (11)0.0204 (10)−0.0005 (9)0.0055 (8)0.0029 (8)
C240.0281 (11)0.0207 (10)0.0229 (10)−0.0018 (8)0.0043 (8)0.0023 (8)
C250.0208 (10)0.0204 (9)0.0170 (9)−0.0005 (8)−0.0003 (7)−0.0018 (7)
C260.0204 (10)0.0187 (9)0.0177 (9)−0.0017 (7)0.0002 (7)−0.0011 (7)
C270.0195 (10)0.0219 (10)0.0180 (9)−0.0034 (8)0.0012 (7)−0.0013 (7)
C280.0257 (11)0.0195 (10)0.0216 (9)−0.0027 (8)0.0011 (8)−0.0021 (8)
C290.0308 (12)0.0267 (11)0.0190 (9)0.0003 (9)0.0005 (8)−0.0061 (8)
C300.0283 (12)0.0313 (11)0.0178 (9)−0.0015 (9)0.0024 (8)−0.0016 (8)
C310.0225 (11)0.0243 (10)0.0167 (9)−0.0016 (8)0.0008 (7)0.0010 (8)
C320.0220 (10)0.0294 (11)0.0150 (9)−0.0035 (8)−0.0005 (7)0.0034 (8)
C330.0245 (12)0.0260 (11)0.0329 (11)0.0019 (9)0.0027 (9)0.0109 (9)
C340.0414 (15)0.0315 (13)0.0588 (16)0.0066 (11)0.0223 (12)0.0217 (12)
C350.0474 (17)0.0239 (13)0.094 (2)0.0018 (11)0.0305 (16)0.0186 (14)
C360.0399 (15)0.0204 (12)0.0781 (19)0.0024 (10)0.0140 (13)0.0025 (12)
C370.0293 (13)0.0219 (11)0.0451 (13)0.0000 (9)0.0026 (10)0.0033 (9)
C380.0218 (11)0.0227 (10)0.0308 (11)0.0013 (8)−0.0016 (8)0.0092 (8)
O10.0415 (10)0.0212 (8)0.0284 (8)−0.0015 (7)−0.0020 (7)0.0066 (6)
O20.0639 (13)0.0310 (9)0.0270 (8)−0.0065 (8)−0.0049 (8)0.0090 (7)
O30.0555 (12)0.0365 (9)0.0293 (8)−0.0049 (8)0.0113 (8)−0.0024 (7)
O40.0396 (10)0.0256 (8)0.0398 (9)−0.0052 (7)0.0011 (7)0.0010 (7)
O50.0525 (12)0.0335 (9)0.0349 (9)−0.0056 (8)0.0030 (8)0.0141 (7)
O60.0740 (15)0.0495 (11)0.0258 (9)0.0124 (10)−0.0063 (8)−0.0024 (8)
O70.0587 (12)0.0321 (9)0.0459 (10)0.0147 (8)0.0166 (9)0.0028 (8)
N110.0336 (11)0.0282 (10)0.0261 (9)−0.0085 (8)−0.0004 (8)0.0037 (8)
N120.0258 (10)0.0268 (10)0.0350 (10)−0.0025 (8)0.0017 (8)0.0096 (8)
N130.0301 (11)0.0321 (10)0.0304 (10)0.0032 (8)0.0066 (8)0.0009 (8)
C390.0198 (11)0.0252 (11)0.0269 (10)0.0019 (8)−0.0003 (8)0.0061 (8)
C400.0240 (11)0.0263 (11)0.0218 (10)−0.0032 (8)0.0001 (8)0.0055 (8)
C410.0219 (11)0.0269 (11)0.0264 (10)−0.0028 (8)−0.0003 (8)0.0013 (9)
C420.0225 (11)0.0230 (10)0.0297 (11)−0.0027 (8)0.0007 (8)0.0071 (8)
C430.0218 (11)0.0300 (11)0.0260 (10)0.0001 (9)0.0025 (8)0.0088 (9)
C440.0214 (11)0.0260 (11)0.0246 (10)0.0020 (8)0.0026 (8)0.0021 (8)
O80.0454 (10)0.0187 (7)0.0262 (8)−0.0029 (7)0.0034 (7)−0.0021 (6)
O90.0354 (9)0.0271 (8)0.0260 (7)−0.0073 (7)0.0045 (6)0.0026 (6)
O100.0389 (10)0.0425 (9)0.0220 (7)−0.0096 (7)−0.0042 (6)−0.0048 (7)
O110.0667 (13)0.0230 (8)0.0463 (10)−0.0078 (8)−0.0019 (9)−0.0069 (8)
O120.0429 (11)0.0315 (9)0.0438 (10)−0.0112 (8)0.0002 (8)0.0125 (7)
O130.0507 (11)0.0512 (11)0.0217 (8)−0.0048 (8)0.0104 (7)−0.0016 (7)
O140.0414 (10)0.0280 (8)0.0311 (8)−0.0033 (7)−0.0014 (7)−0.0070 (6)
N140.0222 (9)0.0250 (9)0.0228 (8)−0.0004 (7)0.0006 (7)−0.0006 (7)
N150.0299 (11)0.0218 (9)0.0416 (11)−0.0046 (8)−0.0046 (8)0.0022 (8)
N160.0279 (10)0.0278 (9)0.0219 (8)0.0071 (8)0.0020 (7)−0.0008 (7)
C450.0194 (10)0.0198 (10)0.0239 (10)−0.0011 (8)0.0029 (8)−0.0015 (8)
C460.0210 (10)0.0210 (10)0.0203 (9)−0.0003 (8)0.0019 (7)0.0010 (8)
C470.0197 (10)0.0239 (10)0.0253 (10)−0.0004 (8)−0.0005 (8)−0.0046 (8)
C480.0222 (11)0.0182 (10)0.0327 (11)−0.0013 (8)0.0004 (8)0.0021 (8)
C490.0210 (11)0.0255 (10)0.0239 (10)0.0019 (8)0.0033 (8)0.0036 (8)
C500.0210 (11)0.0229 (10)0.0194 (9)−0.0002 (8)0.0010 (7)−0.0029 (8)
O160.0338 (10)0.0559 (11)0.0443 (10)−0.0117 (8)0.0048 (8)0.0139 (8)
N180.0356 (11)0.0314 (10)0.0258 (9)−0.0022 (8)0.0030 (8)0.0036 (8)
C540.088 (2)0.0507 (17)0.0353 (14)−0.0159 (16)−0.0174 (14)0.0164 (13)
C550.0409 (16)0.0618 (18)0.0374 (13)−0.0176 (13)0.0032 (11)0.0024 (12)
C560.0298 (13)0.0406 (13)0.0325 (12)0.0006 (10)0.0074 (10)0.0092 (10)
O150.0400 (10)0.0783 (11)0.0301 (6)−0.0152 (7)0.0030 (6)0.0053 (6)
N170.0400 (10)0.0783 (11)0.0301 (6)−0.0152 (7)0.0030 (6)0.0053 (6)
C510.0400 (10)0.0783 (11)0.0301 (6)−0.0152 (7)0.0030 (6)0.0053 (6)
C520.0400 (10)0.0783 (11)0.0301 (6)−0.0152 (7)0.0030 (6)0.0053 (6)
C530.0400 (10)0.0783 (11)0.0301 (6)−0.0152 (7)0.0030 (6)0.0053 (6)
O15'0.0400 (10)0.0783 (11)0.0301 (6)−0.0152 (7)0.0030 (6)0.0053 (6)
N17'0.0400 (10)0.0783 (11)0.0301 (6)−0.0152 (7)0.0030 (6)0.0053 (6)
C51'0.0400 (10)0.0783 (11)0.0301 (6)−0.0152 (7)0.0030 (6)0.0053 (6)
C52'0.0400 (10)0.0783 (11)0.0301 (6)−0.0152 (7)0.0030 (6)0.0053 (6)
C53'0.0400 (10)0.0783 (11)0.0301 (6)−0.0152 (7)0.0030 (6)0.0053 (6)

Geometric parameters (Å, °)

Ni—N82.0393 (16)C33—C381.405 (3)
Ni—N32.0469 (16)C34—C351.373 (4)
Ni—N92.1059 (16)C34—H34A0.9500
Ni—N62.1128 (16)C35—C361.398 (4)
Ni—N12.1134 (17)C35—H35A0.9500
Ni—N42.1182 (16)C36—C371.377 (3)
N1—C71.328 (3)C36—H36A0.9500
N1—C11.387 (2)C37—C381.397 (3)
N2—C71.351 (3)C37—H37A0.9500
N2—C61.390 (3)O1—C391.249 (2)
N2—H2B0.8800O2—N111.230 (2)
N3—C81.337 (3)O3—N111.228 (2)
N3—C121.339 (2)O4—N121.227 (2)
N4—C131.330 (2)O5—N121.238 (2)
N4—C191.380 (3)O6—N131.230 (2)
N5—C131.345 (3)O7—N131.227 (2)
N5—C141.380 (3)N11—C401.454 (3)
N5—H5B0.8800N12—C421.449 (3)
N6—C261.327 (2)N13—C441.453 (3)
N6—C201.385 (2)C39—C441.449 (3)
N7—C261.351 (2)C39—C401.451 (3)
N7—C251.385 (2)C40—C411.370 (3)
N7—H7A0.8800C41—C421.390 (3)
N8—C271.334 (2)C41—H41A0.9500
N8—C311.343 (2)C42—C431.378 (3)
N9—C321.327 (3)C43—C441.369 (3)
N9—C381.378 (3)C43—H43A0.9500
N10—C321.348 (2)O8—C451.243 (2)
N10—C331.375 (3)O9—N141.229 (2)
N10—H10B0.8800O10—N141.233 (2)
C1—C21.392 (3)O11—N151.226 (2)
C1—C61.401 (3)O12—N151.235 (2)
C2—C31.378 (3)O13—N161.235 (2)
C2—H2A0.9500O14—N161.224 (2)
C3—C41.402 (3)N14—C461.459 (2)
C3—H3A0.9500N15—C481.446 (3)
C4—C51.377 (3)N16—C501.453 (2)
C4—H4A0.9500C45—C501.455 (3)
C5—C61.387 (3)C45—C461.455 (3)
C5—H5A0.9500C46—C471.368 (3)
C7—C81.466 (3)C47—C481.388 (3)
C8—C91.387 (3)C47—H47A0.9500
C9—C101.396 (3)C48—C491.382 (3)
C9—H9A0.9500C49—C501.362 (3)
C10—C111.380 (3)C49—H49A0.9500
C10—H10A0.9500O16—C561.241 (3)
C11—C121.400 (3)N18—C561.314 (3)
C11—H11A0.9500N18—C541.445 (3)
C12—C131.457 (3)N18—C551.454 (3)
C14—C151.387 (3)C54—H54A0.9800
C14—C191.408 (3)C54—H54B0.9800
C15—C161.375 (3)C54—H54C0.9800
C15—H15A0.9500C55—H55A0.9800
C16—C171.406 (3)C55—H55B0.9800
C16—H16A0.9500C55—H55C0.9800
C17—C181.378 (3)C56—H560.9500
C17—H17A0.9500O15—C531.230 (4)
C18—C191.399 (3)N17—C531.317 (4)
C18—H18A0.9500N17—C511.440 (4)
C20—C211.399 (3)N17—C521.445 (3)
C20—C251.400 (3)C51—H51A0.9800
C21—C221.374 (3)C51—H51B0.9800
C21—H21A0.9500C51—H51C0.9800
C22—C231.398 (3)C52—H52A0.9800
C22—H22A0.9500C52—H52B0.9800
C23—C241.380 (3)C52—H52C0.9800
C23—H23A0.9500C53—H530.9500
C24—C251.388 (3)O15'—C53'1.223 (6)
C24—H24A0.9500N17'—C53'1.327 (5)
C26—C271.466 (3)N17'—C52'1.431 (4)
C27—C281.394 (3)N17'—C51'1.444 (4)
C28—C291.385 (3)C51'—H51D0.9800
C28—H28A0.9500C51'—H51E0.9800
C29—C301.386 (3)C51'—H51F0.9800
C29—H29A0.9500C52'—H52D0.9800
C30—C311.384 (3)C52'—H52E0.9800
C30—H30A0.9500C52'—H52F0.9800
C31—C321.461 (3)C53'—H53'0.9500
C33—C341.390 (3)
N8—Ni—N3171.79 (7)C29—C30—H30A121.2
N8—Ni—N977.21 (6)N8—C31—C30121.77 (18)
N3—Ni—N9110.07 (6)N8—C31—C32110.29 (17)
N8—Ni—N677.17 (6)C30—C31—C32127.93 (18)
N3—Ni—N695.78 (6)N9—C32—N10113.13 (18)
N9—Ni—N6154.04 (6)N9—C32—C31119.69 (17)
N8—Ni—N199.23 (6)N10—C32—C31126.95 (18)
N3—Ni—N176.69 (6)N10—C33—C34131.7 (2)
N9—Ni—N195.38 (6)N10—C33—C38106.15 (18)
N6—Ni—N192.78 (6)C34—C33—C38122.1 (2)
N8—Ni—N4107.44 (6)C35—C34—C33116.0 (2)
N3—Ni—N477.22 (6)C35—C34—H34A122.0
N9—Ni—N487.60 (6)C33—C34—H34A122.0
N6—Ni—N496.09 (6)C34—C35—C36122.8 (2)
N1—Ni—N4153.14 (6)C34—C35—H35A118.6
C7—N1—C1105.07 (17)C36—C35—H35A118.6
C7—N1—Ni112.91 (13)C37—C36—C35121.3 (2)
C1—N1—Ni141.64 (14)C37—C36—H36A119.4
C7—N2—C6106.87 (17)C35—C36—H36A119.4
C7—N2—H2B126.6C36—C37—C38117.1 (2)
C6—N2—H2B126.6C36—C37—H37A121.5
C8—N3—C12120.94 (17)C38—C37—H37A121.5
C8—N3—Ni119.13 (13)N9—C38—C37130.4 (2)
C12—N3—Ni118.83 (13)N9—C38—C33108.83 (18)
C13—N4—C19104.88 (16)C37—C38—C33120.7 (2)
C13—N4—Ni112.17 (13)O3—N11—O2123.00 (18)
C19—N4—Ni139.12 (13)O3—N11—C40118.66 (18)
C13—N5—C14106.56 (16)O2—N11—C40118.32 (18)
C13—N5—H5B126.7O4—N12—O5123.48 (18)
C14—N5—H5B126.7O4—N12—C42118.91 (17)
C26—N6—C20105.18 (15)O5—N12—C42117.61 (18)
C26—N6—Ni112.83 (12)O7—N13—O6122.71 (19)
C20—N6—Ni141.95 (13)O7—N13—C44118.90 (18)
C26—N7—C25106.70 (15)O6—N13—C44118.38 (18)
C26—N7—H7A126.6O1—C39—C44122.38 (19)
C25—N7—H7A126.6O1—C39—C40125.86 (19)
C27—N8—C31120.38 (16)C44—C39—C40111.62 (18)
C27—N8—Ni119.77 (13)C41—C40—C39124.21 (18)
C31—N8—Ni119.65 (13)C41—C40—N11116.26 (18)
C32—N9—C38105.31 (17)C39—C40—N11119.48 (17)
C32—N9—Ni112.81 (13)C40—C41—C42119.15 (19)
C38—N9—Ni141.58 (14)C40—C41—H41A120.4
C32—N10—C33106.56 (17)C42—C41—H41A120.4
C32—N10—H10B126.7C43—C42—C41121.16 (19)
C33—N10—H10B126.7C43—C42—N12119.05 (18)
N1—C1—C2130.0 (2)C41—C42—N12119.79 (19)
N1—C1—C6109.50 (17)C44—C43—C42119.17 (19)
C2—C1—C6120.40 (19)C44—C43—H43A120.4
C3—C2—C1117.6 (2)C42—C43—H43A120.4
C3—C2—H2A121.2C43—C44—C39124.58 (19)
C1—C2—H2A121.2C43—C44—N13116.60 (18)
C2—C3—C4121.2 (2)C39—C44—N13118.79 (18)
C2—C3—H3A119.4O9—N14—O10122.78 (17)
C4—C3—H3A119.4O9—N14—C46119.29 (16)
C5—C4—C3122.1 (2)O10—N14—C46117.90 (17)
C5—C4—H4A119.0O11—N15—O12123.62 (18)
C3—C4—H4A119.0O11—N15—C48118.32 (19)
C4—C5—C6116.4 (2)O12—N15—C48118.06 (18)
C4—C5—H5A121.8O14—N16—O13122.81 (18)
C6—C5—H5A121.8O14—N16—C50119.39 (17)
C5—C6—N2132.2 (2)O13—N16—C50117.77 (18)
C5—C6—C1122.3 (2)O8—C45—C50124.05 (18)
N2—C6—C1105.43 (18)O8—C45—C46124.57 (18)
N1—C7—N2113.08 (17)C50—C45—C46111.30 (17)
N1—C7—C8119.06 (18)C47—C46—C45124.36 (18)
N2—C7—C8127.50 (18)C47—C46—N14116.13 (17)
N3—C8—C9121.59 (18)C45—C46—N14119.50 (17)
N3—C8—C7110.23 (17)C46—C47—C48119.14 (18)
C9—C8—C7128.18 (19)C46—C47—H47A120.4
C8—C9—C10117.5 (2)C48—C47—H47A120.4
C8—C9—H9A121.2C49—C48—C47120.98 (18)
C10—C9—H9A121.2C49—C48—N15119.00 (18)
C11—C10—C9120.99 (19)C47—C48—N15120.02 (18)
C11—C10—H10A119.5C50—C49—C48119.48 (18)
C9—C10—H10A119.5C50—C49—H49A120.3
C10—C11—C12117.86 (18)C48—C49—H49A120.3
C10—C11—H11A121.1C49—C50—N16116.37 (17)
C12—C11—H11A121.1C49—C50—C45124.41 (18)
N3—C12—C11120.99 (19)N16—C50—C45119.22 (17)
N3—C12—C13110.74 (16)C56—N18—C54121.2 (2)
C11—C12—C13128.26 (18)C56—N18—C55122.2 (2)
N4—C13—N5113.55 (18)C54—N18—C55116.5 (2)
N4—C13—C12118.88 (17)N18—C54—H54A109.5
N5—C13—C12127.42 (17)N18—C54—H54B109.5
N5—C14—C15131.81 (18)H54A—C54—H54B109.5
N5—C14—C19105.83 (18)N18—C54—H54C109.5
C15—C14—C19122.36 (19)H54A—C54—H54C109.5
C16—C15—C14116.38 (19)H54B—C54—H54C109.5
C16—C15—H15A121.8N18—C55—H55A109.5
C14—C15—H15A121.8N18—C55—H55B109.5
C15—C16—C17122.1 (2)H55A—C55—H55B109.5
C15—C16—H16A119.0N18—C55—H55C109.5
C17—C16—H16A119.0H55A—C55—H55C109.5
C18—C17—C16121.7 (2)H55B—C55—H55C109.5
C18—C17—H17A119.1O16—C56—N18125.9 (2)
C16—C17—H17A119.1O16—C56—H56117.1
C17—C18—C19116.92 (18)N18—C56—H56117.1
C17—C18—H18A121.5C53—N17—C51122.2 (2)
C19—C18—H18A121.5C53—N17—C52120.5 (3)
N4—C19—C18130.30 (18)C51—N17—C52117.1 (3)
N4—C19—C14109.18 (17)N17—C51—H51A109.5
C18—C19—C14120.52 (19)N17—C51—H51B109.5
N6—C20—C21130.26 (18)H51A—C51—H51B109.5
N6—C20—C25109.25 (16)N17—C51—H51C109.5
C21—C20—C25120.49 (17)H51A—C51—H51C109.5
C22—C21—C20117.37 (19)H51B—C51—H51C109.5
C22—C21—H21A121.3N17—C52—H52A109.5
C20—C21—H21A121.3N17—C52—H52B109.5
C21—C22—C23121.50 (19)H52A—C52—H52B109.5
C21—C22—H22A119.2N17—C52—H52C109.5
C23—C22—H22A119.2H52A—C52—H52C109.5
C24—C23—C22122.05 (19)H52B—C52—H52C109.5
C24—C23—H23A119.0O15—C53—N17125.7 (3)
C22—C23—H23A119.0O15—C53—H53117.1
C23—C24—C25116.48 (19)N17—C53—H53117.1
C23—C24—H24A121.8C53'—N17'—C52'121.7 (3)
C25—C24—H24A121.8C53'—N17'—C51'119.6 (4)
N7—C25—C24132.11 (18)C52'—N17'—C51'118.7 (4)
N7—C25—C20105.80 (16)N17'—C51'—H51D109.5
C24—C25—C20122.09 (18)N17'—C51'—H51E109.5
N6—C26—N7113.06 (16)H51D—C51'—H51E109.5
N6—C26—C27119.17 (17)N17'—C51'—H51F109.5
N7—C26—C27127.76 (17)H51D—C51'—H51F109.5
N8—C27—C28121.57 (17)H51E—C51'—H51F109.5
N8—C27—C26110.80 (16)N17'—C52'—H52D109.5
C28—C27—C26127.63 (18)N17'—C52'—H52E109.5
C29—C28—C27117.55 (18)H52D—C52'—H52E109.5
C29—C28—H28A121.2N17'—C52'—H52F109.5
C27—C28—H28A121.2H52D—C52'—H52F109.5
C28—C29—C30121.10 (19)H52E—C52'—H52F109.5
C28—C29—H29A119.4O15'—C53'—N17'124.8 (6)
C30—C29—H29A119.4O15'—C53'—H53'117.6
C31—C30—C29117.62 (18)N17'—C53'—H53'117.6
C31—C30—H30A121.2
N8—Ni—N1—C7165.53 (14)Ni—N6—C20—C214.8 (4)
N3—Ni—N1—C7−7.21 (13)C26—N6—C20—C250.9 (2)
N9—Ni—N1—C7−116.59 (14)Ni—N6—C20—C25−176.29 (16)
N6—Ni—N1—C788.08 (14)N6—C20—C21—C22179.0 (2)
N4—Ni—N1—C7−21.3 (2)C25—C20—C21—C220.2 (3)
N8—Ni—N1—C1−22.9 (2)C20—C21—C22—C230.5 (3)
N3—Ni—N1—C1164.4 (2)C21—C22—C23—C24−0.4 (3)
N9—Ni—N1—C155.0 (2)C22—C23—C24—C25−0.4 (3)
N6—Ni—N1—C1−100.3 (2)C26—N7—C25—C24179.4 (2)
N4—Ni—N1—C1150.32 (19)C26—N7—C25—C20−0.2 (2)
N8—Ni—N3—C8−47.8 (5)C23—C24—C25—N7−178.4 (2)
N9—Ni—N3—C8104.03 (14)C23—C24—C25—C201.1 (3)
N6—Ni—N3—C8−78.39 (14)N6—C20—C25—N7−0.4 (2)
N1—Ni—N3—C813.11 (14)C21—C20—C25—N7178.61 (18)
N4—Ni—N3—C8−173.35 (15)N6—C20—C25—C24179.88 (18)
N8—Ni—N3—C12120.3 (4)C21—C20—C25—C24−1.1 (3)
N9—Ni—N3—C12−87.88 (15)C20—N6—C26—N7−1.1 (2)
N6—Ni—N3—C1289.70 (14)Ni—N6—C26—N7177.05 (13)
N1—Ni—N3—C12−178.81 (15)C20—N6—C26—C27179.55 (17)
N4—Ni—N3—C12−5.26 (14)Ni—N6—C26—C27−2.3 (2)
N8—Ni—N4—C13−177.33 (13)C25—N7—C26—N60.8 (2)
N3—Ni—N4—C13−4.33 (13)C25—N7—C26—C27−179.87 (19)
N9—Ni—N4—C13106.88 (14)C31—N8—C27—C28−0.8 (3)
N6—Ni—N4—C13−98.90 (13)Ni—N8—C27—C28174.11 (15)
N1—Ni—N4—C139.7 (2)C31—N8—C27—C26179.45 (17)
N8—Ni—N4—C1929.2 (2)Ni—N8—C27—C26−5.6 (2)
N3—Ni—N4—C19−157.8 (2)N6—C26—C27—N85.1 (3)
N9—Ni—N4—C19−46.57 (19)N7—C26—C27—N8−174.14 (19)
N6—Ni—N4—C19107.65 (19)N6—C26—C27—C28−174.60 (19)
N1—Ni—N4—C19−143.76 (18)N7—C26—C27—C286.1 (3)
N8—Ni—N6—C26−0.53 (13)N8—C27—C28—C291.4 (3)
N3—Ni—N6—C26175.20 (14)C26—C27—C28—C29−178.93 (19)
N9—Ni—N6—C26−10.0 (2)C27—C28—C29—C30−0.8 (3)
N1—Ni—N6—C2698.31 (14)C28—C29—C30—C31−0.2 (3)
N4—Ni—N6—C26−107.08 (14)C27—N8—C31—C30−0.3 (3)
N8—Ni—N6—C20176.5 (2)Ni—N8—C31—C30−175.26 (15)
N3—Ni—N6—C20−7.7 (2)C27—N8—C31—C32−179.12 (17)
N9—Ni—N6—C20167.07 (19)Ni—N8—C31—C326.0 (2)
N1—Ni—N6—C20−84.6 (2)C29—C30—C31—N80.8 (3)
N4—Ni—N6—C2070.0 (2)C29—C30—C31—C32179.4 (2)
N3—Ni—N8—C27−27.6 (5)C38—N9—C32—N10−1.8 (2)
N9—Ni—N8—C27179.42 (16)Ni—N9—C32—N10−176.88 (13)
N6—Ni—N8—C273.66 (14)C38—N9—C32—C31173.06 (18)
N1—Ni—N8—C27−87.11 (15)Ni—N9—C32—C31−2.1 (2)
N4—Ni—N8—C2796.10 (15)C33—N10—C32—N91.3 (2)
N3—Ni—N8—C31147.3 (4)C33—N10—C32—C31−173.1 (2)
N9—Ni—N8—C31−5.64 (14)N8—C31—C32—N9−2.3 (3)
N6—Ni—N8—C31178.60 (16)C30—C31—C32—N9179.0 (2)
N1—Ni—N8—C3187.83 (15)N8—C31—C32—N10171.71 (19)
N4—Ni—N8—C31−88.96 (15)C30—C31—C32—N10−7.0 (3)
N8—Ni—N9—C323.86 (14)C32—N10—C33—C34177.4 (2)
N3—Ni—N9—C32−172.18 (13)C32—N10—C33—C38−0.2 (2)
N6—Ni—N9—C3213.3 (2)N10—C33—C34—C35−174.7 (2)
N1—Ni—N9—C32−94.40 (14)C38—C33—C34—C352.6 (4)
N4—Ni—N9—C32112.35 (14)C33—C34—C35—C36−1.7 (4)
N8—Ni—N9—C38−168.6 (2)C34—C35—C36—C37−0.3 (5)
N3—Ni—N9—C3815.4 (2)C35—C36—C37—C381.4 (4)
N6—Ni—N9—C38−159.09 (19)C32—N9—C38—C37−175.3 (2)
N1—Ni—N9—C3893.2 (2)Ni—N9—C38—C37−2.5 (4)
N4—Ni—N9—C38−60.1 (2)C32—N9—C38—C331.5 (2)
C7—N1—C1—C2177.6 (2)Ni—N9—C38—C33174.30 (17)
Ni—N1—C1—C25.7 (4)C36—C37—C38—N9176.0 (2)
C7—N1—C1—C60.7 (2)C36—C37—C38—C33−0.5 (3)
Ni—N1—C1—C6−171.22 (17)N10—C33—C38—N9−0.8 (2)
N1—C1—C2—C3−174.9 (2)C34—C33—C38—N9−178.8 (2)
C6—C1—C2—C31.7 (3)N10—C33—C38—C37176.37 (19)
C1—C2—C3—C4−0.4 (3)C34—C33—C38—C37−1.6 (3)
C2—C3—C4—C5−1.0 (4)O1—C39—C40—C41172.0 (2)
C3—C4—C5—C61.0 (4)C44—C39—C40—C41−3.7 (3)
C4—C5—C6—N2176.8 (2)O1—C39—C40—N11−5.5 (3)
C4—C5—C6—C10.4 (4)C44—C39—C40—N11178.80 (18)
C7—N2—C6—C5−174.8 (3)O3—N11—C40—C41−23.0 (3)
C7—N2—C6—C12.0 (2)O2—N11—C40—C41155.6 (2)
N1—C1—C6—C5175.5 (2)O3—N11—C40—C39154.8 (2)
C2—C1—C6—C5−1.7 (3)O2—N11—C40—C39−26.7 (3)
N1—C1—C6—N2−1.7 (2)C39—C40—C41—C422.2 (3)
C2—C1—C6—N2−178.97 (19)N11—C40—C41—C42179.79 (19)
C1—N1—C7—N20.6 (2)C40—C41—C42—C43−0.5 (3)
Ni—N1—C7—N2175.19 (14)C40—C41—C42—N12178.68 (19)
C1—N1—C7—C8−173.09 (17)O4—N12—C42—C43173.3 (2)
Ni—N1—C7—C81.5 (2)O5—N12—C42—C43−6.1 (3)
C6—N2—C7—N1−1.7 (2)O4—N12—C42—C41−6.0 (3)
C6—N2—C7—C8171.3 (2)O5—N12—C42—C41174.7 (2)
C12—N3—C8—C9−3.1 (3)C41—C42—C43—C440.8 (3)
Ni—N3—C8—C9164.76 (15)N12—C42—C43—C44−178.42 (19)
C12—N3—C8—C7176.67 (17)C42—C43—C44—C39−2.8 (3)
Ni—N3—C8—C7−15.5 (2)C42—C43—C44—N13179.34 (19)
N1—C7—C8—N38.7 (3)O1—C39—C44—C43−171.9 (2)
N2—C7—C8—N3−164.0 (2)C40—C39—C44—C434.0 (3)
N1—C7—C8—C9−171.6 (2)O1—C39—C44—N136.0 (3)
N2—C7—C8—C915.8 (3)C40—C39—C44—N13−178.16 (18)
N3—C8—C9—C101.2 (3)O7—N13—C44—C43−147.2 (2)
C7—C8—C9—C10−178.52 (19)O6—N13—C44—C4331.6 (3)
C8—C9—C10—C111.7 (3)O7—N13—C44—C3934.8 (3)
C9—C10—C11—C12−2.7 (3)O6—N13—C44—C39−146.4 (2)
C8—N3—C12—C112.0 (3)O8—C45—C46—C47−171.9 (2)
Ni—N3—C12—C11−165.83 (14)C50—C45—C46—C475.0 (3)
C8—N3—C12—C13−179.33 (16)O8—C45—C46—N146.9 (3)
Ni—N3—C12—C1312.8 (2)C50—C45—C46—N14−176.16 (17)
C10—C11—C12—N30.8 (3)O9—N14—C46—C47−156.30 (19)
C10—C11—C12—C13−177.54 (19)O10—N14—C46—C4721.6 (3)
C19—N4—C13—N5−0.7 (2)O9—N14—C46—C4524.8 (3)
Ni—N4—C13—N5−163.04 (13)O10—N14—C46—C45−157.34 (19)
C19—N4—C13—C12175.34 (16)C45—C46—C47—C48−0.8 (3)
Ni—N4—C13—C1213.0 (2)N14—C46—C47—C48−179.66 (18)
C14—N5—C13—N40.9 (2)C46—C47—C48—C49−2.5 (3)
C14—N5—C13—C12−174.71 (18)C46—C47—C48—N15177.57 (19)
N3—C12—C13—N4−17.1 (2)O11—N15—C48—C49−167.0 (2)
C11—C12—C13—N4161.46 (19)O12—N15—C48—C4913.0 (3)
N3—C12—C13—N5158.31 (19)O11—N15—C48—C4713.0 (3)
C11—C12—C13—N5−23.2 (3)O12—N15—C48—C47−167.0 (2)
C13—N5—C14—C15178.0 (2)C47—C48—C49—C500.9 (3)
C13—N5—C14—C19−0.7 (2)N15—C48—C49—C50−179.18 (19)
N5—C14—C15—C16−179.7 (2)C48—C49—C50—N16−176.54 (18)
C19—C14—C15—C16−1.2 (3)C48—C49—C50—C454.2 (3)
C14—C15—C16—C17−0.5 (3)O14—N16—C50—C49151.78 (19)
C15—C16—C17—C181.2 (3)O13—N16—C50—C49−26.2 (3)
C16—C17—C18—C19−0.2 (3)O14—N16—C50—C45−28.9 (3)
C13—N4—C19—C18179.4 (2)O13—N16—C50—C45153.13 (19)
Ni—N4—C19—C18−26.0 (3)O8—C45—C50—C49170.2 (2)
C13—N4—C19—C140.2 (2)C46—C45—C50—C49−6.8 (3)
Ni—N4—C19—C14154.82 (15)O8—C45—C50—N16−9.1 (3)
C17—C18—C19—N4179.49 (19)C46—C45—C50—N16173.97 (17)
C17—C18—C19—C14−1.4 (3)C54—N18—C56—O16−2.3 (4)
N5—C14—C19—N40.3 (2)C55—N18—C56—O16−178.0 (2)
C15—C14—C19—N4−178.50 (18)C51—N17—C53—O151.4 (7)
N5—C14—C19—C18−178.95 (17)C52—N17—C53—O15176.0 (4)
C15—C14—C19—C182.2 (3)C52'—N17'—C53'—O15'1(2)
C26—N6—C20—C21−178.0 (2)C51'—N17'—C53'—O15'−177.2 (11)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N7—H7A···O80.881.932.769 (2)158
C24—H24A···O140.952.603.226 (3)124
C28—H28A···O80.952.263.144 (2)155
C51—H51A···O150.982.412.812 (4)104
C51—H51C···O70.982.473.304 (4)143
C54—H54A···O160.982.432.800 (3)102
N2—H2B···O16i0.881.912.777 (2)170
C9—H9A···O16i0.952.553.411 (3)150
N5—H5B···O1ii0.881.812.684 (2)175
N10—H10B···O15iii0.881.922.803 (3)180
C10—H10A···O6iv0.952.593.398 (3)143
C55—H55A···O10v0.982.493.326 (3)143

Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) x+1/2, −y+3/2, z−1/2; (iii) x+1/2, −y+3/2, z−3/2; (iv) −x+3/2, y+1/2, −z+3/2; (v) x, y, z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5079).

References

  • Freire, E., Baggio, S., Muñoz, J. C. & Baggio, R. (2003). Acta Cryst. C59, m299–m301. [PubMed]
  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Rigaku/MSC (2004). RAPID-AUTO Rigaku/MSC, The Woodlans, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

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