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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): m965.
Published online 2009 July 22. doi:  10.1107/S1600536809028207
PMCID: PMC2977364

{N′-[(E)-(5-Bromo-2-oxidophen­yl)(phen­yl)methyl­ene]benzohydrazidato}pyridine­nickel(II)

Abstract

The asymmetric unit of title complex, [Ni(C20H13BrN2O2)(C5H5N)], contains two independent mol­ecules. In each mol­ecule, the central NiII atom has a square-planar environment, formed by the tridentate hydrazone and the monodentate pyridine ligands, with the N atoms in a trans arrangement about the NiII atom.

Related literature

For the coordination properties of aroylhydrazones, see: Ali et al. (2004 [triangle]); Carcelli et al. (1995 [triangle]); Salem (1998 [triangle]); Singh et al. (1982 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m965-scheme1.jpg

Experimental

Crystal data

  • [Ni(C20H13BrN2O2)(C5H5N)]
  • M r = 531.01
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m965-efi1.jpg
  • a = 22.638 (5) Å
  • b = 10.628 (2) Å
  • c = 19.302 (4) Å
  • β = 108.597 (4)°
  • V = 4401.5 (16) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 2.73 mm−1
  • T = 295 K
  • 0.16 × 0.12 × 0.08 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.670, T max = 0.812
  • 22758 measured reflections
  • 7792 independent reflections
  • 4790 reflections with I > 2σ(I)
  • R int = 0.054

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.120
  • S = 1.01
  • 7792 reflections
  • 577 parameters
  • H-atom parameters constrained
  • Δρmax = 0.98 e Å−3
  • Δρmin = −0.64 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809028207/rk2149sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028207/rk2149Isup2.hkl

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

Acknowledgments

This project was supported by the Postgraduate Foundation of Xi’an Polytechnic University (No. Y05–2–09).

supplementary crystallographic information

Comment

The chemistry of aroylhydrazones continues to attract much attention due to their coordination ability to metal ions (Singh et al., 1982; Salem, 1998; Ali et al., 2004.) and their biological activity (Singh et al., 1982; Carcelli et al., 1995.) As an extension of work on the structural characterisation of aroylhydrazone derivatives, the title compound, {N–[(E)–(5-bromo–2–hydroxyphenyl)– (phenyl)methylene]benzohydrazide}pyridinenickel(II) (Fig. 1) was synthesized and its crystal structure is reported here.

Experimental

A DMF solution (5 ml) of N–[(E)–(5–bromo–2–hydroxyphenyl)– (phenyl)methylene]benzohydrazide (0.25 mmol, 0.099 g) was mixed with a methanol solution(5 ml) of NiCl2.6H2O (0.25 mmol, 0.059 g). The mixture was stirred at 298 K for 4 h and then filtered. A red precipitate was produced after about 10 d. A pyridine mixture (5 ml) was used to dissolve the precipitate at 330 K. A red block–shaped crystals were obtained after one month (yield 30%).

Figures

Fig. 1.
The asymmetric unit of title compound, showing the atom–numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius.

Crystal data

[Ni(C20H13BrN2O2)(C5H5N)]F(000) = 2144
Mr = 531.01Dx = 1.603 Mg m3
Monoclinic, P21/cMelting point: 330 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 22.638 (5) ÅCell parameters from 3249 reflections
b = 10.628 (2) Åθ = 2.7–20.5°
c = 19.302 (4) ŵ = 2.73 mm1
β = 108.597 (4)°T = 295 K
V = 4401.5 (16) Å3Block, red
Z = 80.16 × 0.12 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer7792 independent reflections
Radiation source: fine–focus sealed tube4790 reflections with I > 2σ(I)
graphiteRint = 0.054
[var phi] and ω scansθmax = 25.1°, θmin = 1.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −26→26
Tmin = 0.670, Tmax = 0.812k = −11→12
22758 measured reflectionsl = −22→22

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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.0499P)2 + 2.599P] where P = (Fo2 + 2Fc2)/3
7792 reflections(Δ/σ)max = 0.001
577 parametersΔρmax = 0.98 e Å3
0 restraintsΔρmin = −0.64 e Å3

Special details

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 > 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*/Ueq
Ni10.45264 (3)0.42546 (5)0.35981 (3)0.04172 (18)
Ni20.06865 (3)0.81105 (6)0.09736 (3)0.04584 (19)
Br10.75838 (3)0.56368 (6)0.62155 (3)0.0690 (2)
Br20.08512 (3)1.22986 (6)−0.19492 (3)0.0750 (2)
O10.51622 (15)0.3521 (3)0.42990 (17)0.0482 (9)
O20.38672 (15)0.5023 (3)0.29245 (16)0.0459 (8)
O30.04179 (16)0.8259 (3)−0.00067 (17)0.0531 (9)
O40.09816 (16)0.7926 (3)0.19701 (17)0.0528 (9)
N10.45027 (19)0.6751 (4)0.3254 (2)0.0454 (10)
N20.48688 (19)0.5832 (3)0.3720 (2)0.0424 (10)
N30.14700 (19)0.9788 (4)0.1884 (2)0.0481 (10)
N40.11546 (18)0.9555 (4)0.1141 (2)0.0445 (10)
N50.4137 (2)0.2629 (4)0.3344 (2)0.0451 (10)
N60.0205 (2)0.6599 (4)0.0883 (2)0.0479 (10)
C10.5666 (2)0.4064 (4)0.4720 (2)0.0407 (12)
C20.6088 (2)0.3323 (5)0.5247 (3)0.0487 (13)
H20.59830.24900.52960.058*
C30.6643 (3)0.3755 (5)0.5691 (3)0.0525 (14)
H30.69130.32260.60310.063*
C40.6800 (2)0.5010 (5)0.5629 (3)0.0465 (13)
C50.6392 (2)0.5776 (5)0.5140 (3)0.0441 (12)
H50.65010.66130.51120.053*
C60.5815 (2)0.5355 (4)0.4681 (2)0.0381 (11)
C70.5394 (2)0.6220 (4)0.4173 (2)0.0382 (11)
C80.5575 (2)0.7570 (4)0.4182 (2)0.0397 (11)
C90.5777 (2)0.8056 (5)0.3638 (3)0.0524 (13)
H90.57780.75550.32440.063*
C100.5978 (3)0.9289 (5)0.3675 (3)0.0611 (15)
H100.61210.96090.33090.073*
C110.5970 (3)1.0040 (5)0.4246 (3)0.0625 (16)
H110.61081.08680.42710.075*
C120.5758 (3)0.9569 (5)0.4778 (3)0.0674 (17)
H120.57461.00810.51640.081*
C130.5561 (3)0.8340 (5)0.4747 (3)0.0547 (14)
H130.54180.80270.51130.066*
C140.3990 (2)0.6205 (5)0.2858 (3)0.0439 (12)
C150.3525 (2)0.6938 (4)0.2296 (2)0.0439 (12)
C160.3697 (3)0.7823 (5)0.1885 (3)0.0534 (14)
H160.41170.79970.19720.064*
C170.3247 (3)0.8469 (5)0.1335 (3)0.0658 (17)
H170.33670.90640.10530.079*
C180.2630 (3)0.8227 (6)0.1214 (3)0.0649 (16)
H180.23280.86500.08460.078*
C190.2459 (3)0.7356 (5)0.1637 (3)0.0662 (16)
H190.20380.72040.15630.079*
C200.2902 (3)0.6707 (5)0.2168 (3)0.0528 (14)
H200.27810.61040.24440.063*
C210.3517 (3)0.2521 (5)0.3074 (3)0.0586 (15)
H210.32760.32460.30160.070*
C220.3222 (3)0.1399 (6)0.2881 (3)0.0726 (17)
H220.27900.13630.26940.087*
C230.3569 (3)0.0329 (6)0.2967 (3)0.0733 (18)
H230.3376−0.04500.28450.088*
C240.4199 (3)0.0412 (5)0.3230 (3)0.0665 (17)
H240.4444−0.03080.32920.080*
C250.4470 (3)0.1572 (5)0.3405 (3)0.0575 (15)
H250.49030.16270.35730.069*
C260.0544 (2)0.9173 (5)−0.0393 (3)0.0445 (12)
C270.0255 (2)0.9109 (5)−0.1155 (3)0.0513 (13)
H27−0.00020.8426−0.13480.062*
C280.0335 (2)1.0006 (5)−0.1624 (3)0.0550 (14)
H280.01340.9946−0.21240.066*
C290.0727 (2)1.1011 (5)−0.1327 (3)0.0485 (13)
C300.1021 (2)1.1097 (5)−0.0600 (3)0.0458 (12)
H300.12831.1777−0.04210.055*
C310.0942 (2)1.0188 (4)−0.0103 (2)0.0421 (12)
C320.1244 (2)1.0355 (4)0.0670 (3)0.0423 (12)
C330.1665 (2)1.1473 (5)0.0940 (3)0.0466 (13)
C340.1508 (3)1.2401 (5)0.1358 (3)0.0575 (14)
H340.11541.23130.14970.069*
C350.1880 (3)1.3452 (6)0.1565 (3)0.0710 (17)
H350.17761.40780.18430.085*
C360.2398 (3)1.3567 (6)0.1360 (4)0.0786 (19)
H360.26491.42750.15010.094*
C370.2558 (3)1.2651 (6)0.0947 (3)0.0729 (18)
H370.29141.27420.08100.087*
C380.2193 (3)1.1616 (5)0.0740 (3)0.0556 (14)
H380.23011.09980.04610.067*
C390.1347 (2)0.8865 (5)0.2267 (3)0.0479 (13)
C400.1637 (2)0.8869 (5)0.3062 (3)0.0511 (14)
C410.1625 (3)0.7808 (6)0.3465 (3)0.0635 (16)
H410.14160.70940.32350.076*
C420.1923 (3)0.7798 (7)0.4212 (3)0.0754 (18)
H420.19150.70740.44800.090*
C430.2224 (3)0.8831 (8)0.4554 (3)0.086 (2)
H430.24240.88060.50560.103*
C440.2240 (3)0.9913 (7)0.4179 (3)0.084 (2)
H440.24421.06260.44200.100*
C450.1948 (3)0.9922 (6)0.3428 (3)0.0655 (16)
H450.19611.06480.31640.079*
C460.0367 (3)0.5674 (5)0.1383 (3)0.0603 (15)
H460.07330.57570.17750.072*
C470.0011 (3)0.4611 (5)0.1337 (3)0.0710 (18)
H470.01380.39830.16880.085*
C48−0.0532 (3)0.4483 (5)0.0768 (3)0.0689 (17)
H48−0.07830.37760.07310.083*
C49−0.0696 (3)0.5409 (5)0.0261 (3)0.0593 (15)
H49−0.10640.5346−0.01300.071*
C50−0.0321 (3)0.6433 (5)0.0323 (3)0.0525 (14)
H50−0.04350.7045−0.00400.063*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ni10.0482 (4)0.0334 (3)0.0423 (4)0.0018 (3)0.0126 (3)0.0002 (3)
Ni20.0512 (4)0.0451 (4)0.0404 (4)−0.0004 (3)0.0134 (3)0.0040 (3)
Br10.0527 (4)0.0775 (4)0.0669 (4)0.0002 (3)0.0053 (3)0.0001 (3)
Br20.0966 (5)0.0765 (4)0.0472 (3)−0.0218 (4)0.0162 (3)0.0117 (3)
O10.054 (2)0.0325 (19)0.053 (2)−0.0032 (16)0.0097 (18)0.0049 (16)
O20.052 (2)0.035 (2)0.045 (2)−0.0031 (16)0.0067 (16)−0.0012 (16)
O30.067 (2)0.048 (2)0.0408 (19)−0.0117 (18)0.0115 (17)0.0047 (17)
O40.056 (2)0.058 (2)0.043 (2)−0.0069 (19)0.0137 (17)0.0020 (18)
N10.053 (3)0.034 (2)0.046 (2)0.006 (2)0.012 (2)0.006 (2)
N20.052 (3)0.036 (2)0.039 (2)0.003 (2)0.013 (2)0.0034 (19)
N30.051 (3)0.052 (3)0.037 (2)0.002 (2)0.009 (2)0.003 (2)
N40.043 (3)0.053 (3)0.035 (2)0.004 (2)0.0089 (19)0.003 (2)
N50.053 (3)0.038 (2)0.044 (2)0.000 (2)0.015 (2)−0.0012 (19)
N60.056 (3)0.044 (3)0.045 (2)0.001 (2)0.018 (2)0.005 (2)
C10.046 (3)0.039 (3)0.039 (3)0.005 (2)0.016 (2)−0.001 (2)
C20.060 (4)0.035 (3)0.048 (3)0.007 (3)0.014 (3)0.003 (2)
C30.057 (4)0.053 (4)0.045 (3)0.012 (3)0.013 (3)0.004 (3)
C40.043 (3)0.056 (4)0.039 (3)0.002 (3)0.012 (2)−0.004 (3)
C50.049 (3)0.042 (3)0.046 (3)−0.003 (3)0.020 (3)−0.001 (2)
C60.040 (3)0.040 (3)0.035 (3)0.000 (2)0.013 (2)−0.001 (2)
C70.044 (3)0.034 (3)0.040 (3)0.003 (2)0.017 (2)−0.002 (2)
C80.037 (3)0.040 (3)0.041 (3)0.002 (2)0.010 (2)0.008 (2)
C90.059 (4)0.051 (3)0.050 (3)0.000 (3)0.021 (3)0.005 (3)
C100.066 (4)0.055 (4)0.070 (4)−0.001 (3)0.033 (3)0.023 (3)
C110.060 (4)0.041 (3)0.081 (4)−0.006 (3)0.015 (3)0.009 (3)
C120.099 (5)0.046 (4)0.062 (4)−0.010 (3)0.032 (4)−0.004 (3)
C130.079 (4)0.040 (3)0.052 (3)−0.009 (3)0.030 (3)0.002 (3)
C140.048 (3)0.046 (3)0.038 (3)0.003 (3)0.014 (3)−0.002 (2)
C150.059 (4)0.033 (3)0.038 (3)0.006 (3)0.012 (2)−0.006 (2)
C160.056 (4)0.052 (3)0.053 (3)0.004 (3)0.017 (3)0.002 (3)
C170.088 (5)0.058 (4)0.056 (4)0.016 (4)0.030 (3)0.016 (3)
C180.070 (5)0.063 (4)0.053 (4)0.017 (3)0.008 (3)0.004 (3)
C190.049 (4)0.060 (4)0.079 (4)0.011 (3)0.007 (3)−0.007 (3)
C200.058 (4)0.041 (3)0.055 (3)0.006 (3)0.012 (3)−0.001 (3)
C210.058 (4)0.046 (3)0.073 (4)−0.001 (3)0.023 (3)−0.004 (3)
C220.058 (4)0.062 (4)0.096 (5)−0.010 (4)0.022 (4)−0.008 (4)
C230.088 (5)0.049 (4)0.081 (4)−0.020 (4)0.025 (4)−0.020 (3)
C240.079 (5)0.037 (3)0.077 (4)0.007 (3)0.015 (4)−0.008 (3)
C250.065 (4)0.044 (3)0.058 (3)0.008 (3)0.012 (3)−0.005 (3)
C260.052 (3)0.041 (3)0.042 (3)0.002 (3)0.018 (2)−0.002 (2)
C270.061 (4)0.046 (3)0.045 (3)−0.015 (3)0.015 (3)−0.008 (3)
C280.063 (4)0.062 (4)0.039 (3)−0.004 (3)0.014 (3)0.001 (3)
C290.056 (3)0.050 (3)0.042 (3)0.000 (3)0.019 (3)0.003 (3)
C300.050 (3)0.044 (3)0.041 (3)−0.005 (2)0.012 (2)−0.004 (2)
C310.046 (3)0.043 (3)0.040 (3)0.004 (2)0.018 (2)0.000 (2)
C320.044 (3)0.041 (3)0.043 (3)0.003 (2)0.016 (2)0.001 (2)
C330.051 (3)0.042 (3)0.040 (3)−0.002 (3)0.005 (2)0.003 (2)
C340.058 (4)0.057 (4)0.052 (3)0.001 (3)0.009 (3)−0.008 (3)
C350.087 (5)0.053 (4)0.064 (4)0.002 (4)0.012 (4)−0.019 (3)
C360.080 (5)0.061 (4)0.078 (5)−0.021 (4)0.001 (4)−0.014 (4)
C370.067 (4)0.076 (4)0.072 (4)−0.023 (4)0.017 (3)−0.006 (4)
C380.056 (4)0.052 (3)0.058 (3)−0.004 (3)0.017 (3)−0.007 (3)
C390.048 (3)0.056 (4)0.039 (3)0.011 (3)0.013 (3)0.000 (3)
C400.051 (3)0.061 (4)0.044 (3)0.010 (3)0.018 (3)0.004 (3)
C410.071 (4)0.067 (4)0.050 (3)0.010 (3)0.015 (3)0.005 (3)
C420.086 (5)0.082 (5)0.054 (4)0.015 (4)0.016 (4)0.016 (4)
C430.082 (5)0.118 (6)0.047 (4)0.010 (5)0.006 (3)0.005 (4)
C440.091 (5)0.094 (5)0.062 (4)−0.009 (4)0.019 (4)0.008 (4)
C450.070 (4)0.070 (4)0.052 (4)−0.004 (3)0.013 (3)0.006 (3)
C460.082 (4)0.053 (4)0.047 (3)0.002 (3)0.022 (3)0.002 (3)
C470.116 (6)0.048 (4)0.050 (4)−0.003 (4)0.028 (4)0.006 (3)
C480.095 (5)0.056 (4)0.064 (4)−0.016 (3)0.037 (4)−0.001 (3)
C490.062 (4)0.058 (4)0.059 (4)−0.006 (3)0.020 (3)0.001 (3)
C500.059 (4)0.050 (3)0.053 (3)0.002 (3)0.023 (3)0.005 (3)

Geometric parameters (Å, °)

Ni1—O11.808 (3)C19—C201.371 (7)
Ni1—O21.829 (3)C19—H190.9300
Ni1—N21.831 (4)C20—H200.9300
Ni1—N51.930 (4)C21—C221.359 (7)
Ni2—O31.800 (3)C21—H210.9300
Ni2—N41.834 (4)C22—C231.361 (8)
Ni2—O41.834 (3)C22—H220.9300
Ni2—N61.917 (4)C23—C241.357 (8)
Br1—C41.896 (5)C23—H230.9300
Br2—C291.899 (5)C24—C251.371 (7)
O1—C11.305 (5)C24—H240.9300
O2—C141.302 (6)C25—H250.9300
O3—C261.310 (5)C26—C311.402 (6)
O4—C391.305 (6)C26—C271.408 (7)
N1—C141.305 (6)C27—C281.365 (6)
N1—N21.404 (5)C27—H270.9300
N2—C71.298 (6)C28—C291.390 (7)
N3—C391.311 (6)C28—H280.9300
N3—N41.405 (5)C29—C301.351 (6)
N4—C321.307 (6)C30—C311.413 (6)
N5—C211.337 (6)C30—H300.9300
N5—C251.338 (6)C31—C321.440 (6)
N6—C501.341 (6)C32—C331.508 (7)
N6—C461.344 (6)C33—C381.377 (7)
C1—C21.395 (6)C33—C341.389 (7)
C1—C61.421 (6)C34—C351.379 (8)
C2—C31.354 (7)C34—H340.9300
C2—H20.9300C35—C361.357 (8)
C3—C41.396 (7)C35—H350.9300
C3—H30.9300C36—C371.379 (8)
C4—C51.359 (6)C36—H360.9300
C5—C61.397 (6)C37—C381.356 (7)
C5—H50.9300C37—H370.9300
C6—C71.455 (6)C38—H380.9300
C7—C81.491 (6)C39—C401.465 (7)
C8—C91.371 (6)C40—C411.375 (7)
C8—C131.372 (6)C40—C451.389 (7)
C9—C101.381 (7)C41—C421.383 (8)
C9—H90.9300C41—H410.9300
C10—C111.366 (7)C42—C431.348 (9)
C10—H100.9300C42—H420.9300
C11—C121.359 (7)C43—C441.367 (9)
C11—H110.9300C43—H430.9300
C12—C131.376 (7)C44—C451.388 (8)
C12—H120.9300C44—H440.9300
C13—H130.9300C45—H450.9300
C14—C151.470 (7)C46—C471.374 (7)
C15—C161.364 (7)C46—H460.9300
C15—C201.374 (7)C47—C481.370 (8)
C16—C171.395 (7)C47—H470.9300
C16—H160.9300C48—C491.354 (7)
C17—C181.364 (8)C48—H480.9300
C17—H170.9300C49—C501.362 (7)
C18—C191.370 (8)C49—H490.9300
C18—H180.9300C50—H500.9300
O1—Ni1—O2177.13 (15)N5—C21—C22123.0 (5)
O1—Ni1—N295.47 (16)N5—C21—H21118.5
O2—Ni1—N284.18 (16)C22—C21—H21118.5
O1—Ni1—N589.70 (16)C21—C22—C23119.1 (6)
O2—Ni1—N590.88 (16)C21—C22—H22120.4
N2—Ni1—N5173.05 (16)C23—C22—H22120.4
O3—Ni2—N495.41 (16)C24—C23—C22119.1 (6)
O3—Ni2—O4178.09 (17)C24—C23—H23120.4
N4—Ni2—O484.71 (16)C22—C23—H23120.4
O3—Ni2—N689.21 (16)C23—C24—C25119.1 (5)
N4—Ni2—N6175.27 (17)C23—C24—H24120.5
O4—Ni2—N690.72 (16)C25—C24—H24120.5
C1—O1—Ni1127.2 (3)N5—C25—C24122.5 (5)
C14—O2—Ni1110.5 (3)N5—C25—H25118.7
C26—O3—Ni2127.0 (3)C24—C25—H25118.7
C39—O4—Ni2110.3 (3)O3—C26—C31124.8 (4)
C14—N1—N2107.4 (4)O3—C26—C27116.5 (4)
C7—N2—N1116.0 (4)C31—C26—C27118.7 (4)
C7—N2—Ni1129.5 (3)C28—C27—C26122.9 (5)
N1—N2—Ni1114.5 (3)C28—C27—H27118.6
C39—N3—N4108.2 (4)C26—C27—H27118.6
C32—N4—N3117.0 (4)C27—C28—C29117.8 (5)
C32—N4—Ni2129.1 (3)C27—C28—H28121.1
N3—N4—Ni2113.9 (3)C29—C28—H28121.1
C21—N5—C25117.1 (5)C30—C29—C28121.2 (5)
C21—N5—Ni1120.9 (4)C30—C29—Br2119.0 (4)
C25—N5—Ni1122.0 (4)C28—C29—Br2119.8 (4)
C50—N6—C46116.9 (5)C29—C30—C31122.2 (5)
C50—N6—Ni2121.1 (3)C29—C30—H30118.9
C46—N6—Ni2122.0 (4)C31—C30—H30118.9
O1—C1—C2117.7 (4)C26—C31—C30117.3 (4)
O1—C1—C6124.7 (4)C26—C31—C32122.8 (4)
C2—C1—C6117.7 (5)C30—C31—C32119.9 (4)
C3—C2—C1123.5 (5)N4—C32—C31120.8 (4)
C3—C2—H2118.3N4—C32—C33119.5 (4)
C1—C2—H2118.3C31—C32—C33119.6 (4)
C2—C3—C4118.6 (5)C38—C33—C34119.3 (5)
C2—C3—H3120.7C38—C33—C32119.9 (5)
C4—C3—H3120.7C34—C33—C32120.7 (5)
C5—C4—C3119.8 (5)C35—C34—C33120.0 (6)
C5—C4—Br1120.2 (4)C35—C34—H34120.0
C3—C4—Br1120.0 (4)C33—C34—H34120.0
C4—C5—C6122.6 (5)C36—C35—C34119.4 (6)
C4—C5—H5118.7C36—C35—H35120.3
C6—C5—H5118.7C34—C35—H35120.3
C5—C6—C1117.7 (4)C35—C36—C37121.1 (6)
C5—C6—C7120.3 (4)C35—C36—H36119.5
C1—C6—C7122.0 (4)C37—C36—H36119.5
N2—C7—C6121.1 (4)C38—C37—C36119.7 (6)
N2—C7—C8120.1 (4)C38—C37—H37120.2
C6—C7—C8118.8 (4)C36—C37—H37120.2
C9—C8—C13118.7 (5)C37—C38—C33120.6 (5)
C9—C8—C7120.8 (4)C37—C38—H38119.7
C13—C8—C7120.4 (4)C33—C38—H38119.7
C8—C9—C10120.2 (5)O4—C39—N3123.0 (4)
C8—C9—H9119.9O4—C39—C40118.2 (5)
C10—C9—H9119.9N3—C39—C40118.9 (5)
C11—C10—C9120.4 (5)C41—C40—C45118.1 (5)
C11—C10—H10119.8C41—C40—C39120.5 (5)
C9—C10—H10119.8C45—C40—C39121.4 (5)
C12—C11—C10119.5 (5)C40—C41—C42120.4 (6)
C12—C11—H11120.2C40—C41—H41119.8
C10—C11—H11120.2C42—C41—H41119.8
C11—C12—C13120.3 (5)C43—C42—C41120.4 (6)
C11—C12—H12119.9C43—C42—H42119.8
C13—C12—H12119.9C41—C42—H42119.8
C8—C13—C12120.8 (5)C42—C43—C44121.4 (6)
C8—C13—H13119.6C42—C43—H43119.3
C12—C13—H13119.6C44—C43—H43119.3
O2—C14—N1123.2 (4)C43—C44—C45118.3 (7)
O2—C14—C15117.4 (4)C43—C44—H44120.8
N1—C14—C15119.4 (5)C45—C44—H44120.8
C16—C15—C20119.0 (5)C44—C45—C40121.4 (6)
C16—C15—C14121.6 (5)C44—C45—H45119.3
C20—C15—C14119.3 (5)C40—C45—H45119.3
C15—C16—C17120.4 (5)N6—C46—C47122.3 (6)
C15—C16—H16119.8N6—C46—H46118.9
C17—C16—H16119.8C47—C46—H46118.9
C18—C17—C16119.8 (5)C48—C47—C46119.5 (6)
C18—C17—H17120.1C48—C47—H47120.2
C16—C17—H17120.1C46—C47—H47120.2
C17—C18—C19119.6 (5)C49—C48—C47118.4 (6)
C17—C18—H18120.2C49—C48—H48120.8
C19—C18—H18120.2C47—C48—H48120.8
C18—C19—C20120.4 (6)C48—C49—C50119.9 (6)
C18—C19—H19119.8C48—C49—H49120.1
C20—C19—H19119.8C50—C49—H49120.1
C19—C20—C15120.6 (5)N6—C50—C49123.0 (5)
C19—C20—H20119.7N6—C50—H50118.5
C15—C20—H20119.7C49—C50—H50118.5
N2—Ni1—O1—C11.1 (4)C15—C16—C17—C180.8 (8)
N5—Ni1—O1—C1176.4 (4)C16—C17—C18—C190.5 (8)
N2—Ni1—O2—C143.2 (3)C17—C18—C19—C20−1.6 (9)
N5—Ni1—O2—C14−171.9 (3)C18—C19—C20—C151.5 (8)
N4—Ni2—O3—C26−1.4 (4)C16—C15—C20—C19−0.2 (7)
N6—Ni2—O3—C26177.5 (4)C14—C15—C20—C19−178.6 (5)
N4—Ni2—O4—C390.4 (3)C25—N5—C21—C221.5 (8)
N6—Ni2—O4—C39−178.4 (3)Ni1—N5—C21—C22179.4 (4)
C14—N1—N2—C7−178.1 (4)N5—C21—C22—C230.3 (9)
C14—N1—N2—Ni11.6 (5)C21—C22—C23—C24−1.1 (9)
O1—Ni1—N2—C7−0.2 (4)C22—C23—C24—C250.1 (9)
O2—Ni1—N2—C7176.9 (4)C21—N5—C25—C24−2.5 (8)
O1—Ni1—N2—N1−179.9 (3)Ni1—N5—C25—C24179.6 (4)
O2—Ni1—N2—N1−2.7 (3)C23—C24—C25—N51.8 (9)
C39—N3—N4—C32−177.2 (4)Ni2—O3—C26—C313.0 (7)
C39—N3—N4—Ni21.1 (5)Ni2—O3—C26—C27−177.2 (3)
O3—Ni2—N4—C32−1.0 (4)O3—C26—C27—C28178.8 (5)
O4—Ni2—N4—C32177.1 (4)C31—C26—C27—C28−1.3 (8)
O3—Ni2—N4—N3−178.9 (3)C26—C27—C28—C290.9 (8)
O4—Ni2—N4—N3−0.8 (3)C27—C28—C29—C300.2 (8)
O1—Ni1—N5—C21150.0 (4)C27—C28—C29—Br2−179.4 (4)
O2—Ni1—N5—C21−27.2 (4)C28—C29—C30—C31−0.8 (8)
O1—Ni1—N5—C25−32.2 (4)Br2—C29—C30—C31178.8 (4)
O2—Ni1—N5—C25150.7 (4)O3—C26—C31—C30−179.5 (4)
O3—Ni2—N6—C50−29.6 (4)C27—C26—C31—C300.7 (7)
O4—Ni2—N6—C50152.3 (4)O3—C26—C31—C32−2.0 (8)
O3—Ni2—N6—C46152.2 (4)C27—C26—C31—C32178.1 (5)
O4—Ni2—N6—C46−25.9 (4)C29—C30—C31—C260.3 (7)
Ni1—O1—C1—C2177.6 (3)C29—C30—C31—C32−177.2 (5)
Ni1—O1—C1—C6−2.5 (7)N3—N4—C32—C31179.8 (4)
O1—C1—C2—C3176.3 (4)Ni2—N4—C32—C311.9 (7)
C6—C1—C2—C3−3.6 (7)N3—N4—C32—C33−0.8 (6)
C1—C2—C3—C40.9 (8)Ni2—N4—C32—C33−178.6 (3)
C2—C3—C4—C51.5 (7)C26—C31—C32—N4−0.4 (7)
C2—C3—C4—Br1−177.8 (4)C30—C31—C32—N4176.9 (4)
C3—C4—C5—C6−1.1 (7)C26—C31—C32—C33−179.9 (4)
Br1—C4—C5—C6178.2 (3)C30—C31—C32—C33−2.6 (7)
C4—C5—C6—C1−1.6 (7)N4—C32—C33—C38118.7 (5)
C4—C5—C6—C7179.4 (4)C31—C32—C33—C38−61.9 (6)
O1—C1—C6—C5−176.1 (4)N4—C32—C33—C34−64.9 (6)
C2—C1—C6—C53.8 (6)C31—C32—C33—C34114.6 (5)
O1—C1—C6—C72.9 (7)C38—C33—C34—C350.2 (8)
C2—C1—C6—C7−177.2 (4)C32—C33—C34—C35−176.3 (5)
N1—N2—C7—C6−179.7 (4)C33—C34—C35—C36−0.3 (9)
Ni1—N2—C7—C60.7 (7)C34—C35—C36—C370.2 (10)
N1—N2—C7—C80.5 (6)C35—C36—C37—C380.0 (10)
Ni1—N2—C7—C8−179.2 (3)C36—C37—C38—C330.0 (9)
C5—C6—C7—N2177.0 (4)C34—C33—C38—C37−0.1 (8)
C1—C6—C7—N2−1.9 (7)C32—C33—C38—C37176.4 (5)
C5—C6—C7—C8−3.1 (6)Ni2—O4—C39—N30.1 (6)
C1—C6—C7—C8178.0 (4)Ni2—O4—C39—C40−178.9 (3)
N2—C7—C8—C9−74.7 (6)N4—N3—C39—O4−0.8 (6)
C6—C7—C8—C9105.4 (5)N4—N3—C39—C40178.2 (4)
N2—C7—C8—C13107.3 (5)O4—C39—C40—C4112.4 (7)
C6—C7—C8—C13−72.5 (6)N3—C39—C40—C41−166.6 (5)
C13—C8—C9—C101.9 (7)O4—C39—C40—C45−169.5 (5)
C7—C8—C9—C10−176.1 (5)N3—C39—C40—C4511.5 (8)
C8—C9—C10—C11−1.0 (8)C45—C40—C41—C42−0.8 (8)
C9—C10—C11—C12−0.4 (9)C39—C40—C41—C42177.3 (5)
C10—C11—C12—C130.9 (9)C40—C41—C42—C430.6 (10)
C9—C8—C13—C12−1.3 (8)C41—C42—C43—C440.5 (11)
C7—C8—C13—C12176.6 (5)C42—C43—C44—C45−1.2 (10)
C11—C12—C13—C8−0.1 (9)C43—C44—C45—C400.9 (10)
Ni1—O2—C14—N1−3.5 (6)C41—C40—C45—C440.1 (9)
Ni1—O2—C14—C15175.5 (3)C39—C40—C45—C44−178.0 (5)
N2—N1—C14—O21.3 (6)C50—N6—C46—C47−0.9 (7)
N2—N1—C14—C15−177.7 (4)Ni2—N6—C46—C47177.4 (4)
O2—C14—C15—C16−141.4 (5)N6—C46—C47—C48−0.8 (9)
N1—C14—C15—C1637.6 (7)C46—C47—C48—C491.0 (9)
O2—C14—C15—C2036.9 (6)C47—C48—C49—C500.3 (9)
N1—C14—C15—C20−144.1 (5)C46—N6—C50—C492.3 (7)
C20—C15—C16—C17−1.0 (7)Ni2—N6—C50—C49−176.0 (4)
C14—C15—C16—C17177.4 (5)C48—C49—C50—N6−2.1 (8)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2149).

References

  • Ali, H. M., Khamis, N. A. & Yamin, B. M. (2004). Acta Cryst. E60, m1708–m1709.
  • Bruker (2005). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Carcelli, M., Mazza, P., Pelizzi, G. & Zani, F. (1995). J. Inorg. Biochem.57, 43–62. [PubMed]
  • Salem, A. A. (1998). Microchem. J.60, 51–66.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Singh, R. B., Jain, P. & Singh, R. P. (1982). Talanta, 29, 77–84. [PubMed]

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