metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

aCollege of Environmental and Chemical Engineering, Xi'an Polytechnic University, Xi'an, Shaanxi 710048, People's Republic of China, bSchool of Chemistry & Pharmaceutical Engineering, Sichuan University of Science & Engineering, Zigong, Sichuan 643000, People's Republic of China, and cLiaoning Key Laboratory of Applied Chemistry, Institute of Superfine Chemicals, Bohai University, Jinzhou 121000, People's Republic of China
*Correspondence e-mail: jichangyou789456@126.com

(Received 18 May 2009; accepted 17 July 2009; online 22 July 2009)

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[Ali, H. M., Khamis, N. A. & Yamin, B. M. (2004). Acta Cryst. E60, m1708-m1709.]); Carcelli et al. (1995[Carcelli, M., Mazza, P., Pelizzi, G. & Zani, F. (1995). J. Inorg. Biochem. 57, 43-62.]); Salem (1998[Salem, A. A. (1998). Microchem. J. 60, 51-66.]); Singh et al. (1982[Singh, R. B., Jain, P. & Singh, R. P. (1982). Talanta, 29, 77-84.]).

[Scheme 1]

Experimental

Crystal data
  • [Ni(C20H13BrN2O2)(C5H5N)]

  • Mr = 531.01

  • Monoclinic, P 21 /c

  • 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[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.670, Tmax = 0.812

  • 22758 measured reflections

  • 7792 independent reflections

  • 4790 reflections with I > 2σ(I)

  • Rint = 0.054

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 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[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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.

Related literature top

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

Experimental top

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%).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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
[Figure 1] 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.
{N'-[(E)-(5-Bromo-2- oxidophenyl)(phenyl)methylene]benzohydrazidato}pyridinenickel(II) top
Crystal data top
[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 top
Bruker APEXII CCD area-detector
diffractometer
7792 independent reflections
Radiation source: fine–focus sealed tube4790 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
ϕ and ω scansθmax = 25.1°, θmin = 1.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 2626
Tmin = 0.670, Tmax = 0.812k = 1112
22758 measured reflectionsl = 2222
Refinement top
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 = 1.01 w = 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
Crystal data top
[Ni(C20H13BrN2O2)(C5H5N)]V = 4401.5 (16) Å3
Mr = 531.01Z = 8
Monoclinic, P21/cMo Kα radiation
a = 22.638 (5) ŵ = 2.73 mm1
b = 10.628 (2) ÅT = 295 K
c = 19.302 (4) Å0.16 × 0.12 × 0.08 mm
β = 108.597 (4)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
7792 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
4790 reflections with I > 2σ(I)
Tmin = 0.670, Tmax = 0.812Rint = 0.054
22758 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.120H-atom parameters constrained
S = 1.01Δρmax = 0.98 e Å3
7792 reflectionsΔρmin = 0.64 e Å3
577 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R–factor wR and goodness of fit S are based on F2, conventional R–factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 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) top
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)
H230.33760.04500.28450.088*
C240.4199 (3)0.0412 (5)0.3230 (3)0.0665 (17)
H240.44440.03080.32920.080*
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)
H270.00020.84260.13480.062*
C280.0335 (2)1.0006 (5)0.1624 (3)0.0550 (14)
H280.01340.99460.21240.066*
C290.0727 (2)1.1011 (5)0.1327 (3)0.0485 (13)
C300.1021 (2)1.1097 (5)0.0600 (3)0.0458 (12)
H300.12831.17770.04210.055*
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*
C480.0532 (3)0.4483 (5)0.0768 (3)0.0689 (17)
H480.07830.37760.07310.083*
C490.0696 (3)0.5409 (5)0.0261 (3)0.0593 (15)
H490.10640.53460.01300.071*
C500.0321 (3)0.6433 (5)0.0323 (3)0.0525 (14)
H500.04350.70450.00400.063*
Atomic displacement parameters (Å2) top
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, º) top
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—C201.6 (9)
N5—Ni1—O2—C14171.9 (3)C18—C19—C20—C151.5 (8)
N4—Ni2—O3—C261.4 (4)C16—C15—C20—C190.2 (7)
N6—Ni2—O3—C26177.5 (4)C14—C15—C20—C19178.6 (5)
N4—Ni2—O4—C390.4 (3)C25—N5—C21—C221.5 (8)
N6—Ni2—O4—C39178.4 (3)Ni1—N5—C21—C22179.4 (4)
C14—N1—N2—C7178.1 (4)N5—C21—C22—C230.3 (9)
C14—N1—N2—Ni11.6 (5)C21—C22—C23—C241.1 (9)
O1—Ni1—N2—C70.2 (4)C22—C23—C24—C250.1 (9)
O2—Ni1—N2—C7176.9 (4)C21—N5—C25—C242.5 (8)
O1—Ni1—N2—N1179.9 (3)Ni1—N5—C25—C24179.6 (4)
O2—Ni1—N2—N12.7 (3)C23—C24—C25—N51.8 (9)
C39—N3—N4—C32177.2 (4)Ni2—O3—C26—C313.0 (7)
C39—N3—N4—Ni21.1 (5)Ni2—O3—C26—C27177.2 (3)
O3—Ni2—N4—C321.0 (4)O3—C26—C27—C28178.8 (5)
O4—Ni2—N4—C32177.1 (4)C31—C26—C27—C281.3 (8)
O3—Ni2—N4—N3178.9 (3)C26—C27—C28—C290.9 (8)
O4—Ni2—N4—N30.8 (3)C27—C28—C29—C300.2 (8)
O1—Ni1—N5—C21150.0 (4)C27—C28—C29—Br2179.4 (4)
O2—Ni1—N5—C2127.2 (4)C28—C29—C30—C310.8 (8)
O1—Ni1—N5—C2532.2 (4)Br2—C29—C30—C31178.8 (4)
O2—Ni1—N5—C25150.7 (4)O3—C26—C31—C30179.5 (4)
O3—Ni2—N6—C5029.6 (4)C27—C26—C31—C300.7 (7)
O4—Ni2—N6—C50152.3 (4)O3—C26—C31—C322.0 (8)
O3—Ni2—N6—C46152.2 (4)C27—C26—C31—C32178.1 (5)
O4—Ni2—N6—C4625.9 (4)C29—C30—C31—C260.3 (7)
Ni1—O1—C1—C2177.6 (3)C29—C30—C31—C32177.2 (5)
Ni1—O1—C1—C62.5 (7)N3—N4—C32—C31179.8 (4)
O1—C1—C2—C3176.3 (4)Ni2—N4—C32—C311.9 (7)
C6—C1—C2—C33.6 (7)N3—N4—C32—C330.8 (6)
C1—C2—C3—C40.9 (8)Ni2—N4—C32—C33178.6 (3)
C2—C3—C4—C51.5 (7)C26—C31—C32—N40.4 (7)
C2—C3—C4—Br1177.8 (4)C30—C31—C32—N4176.9 (4)
C3—C4—C5—C61.1 (7)C26—C31—C32—C33179.9 (4)
Br1—C4—C5—C6178.2 (3)C30—C31—C32—C332.6 (7)
C4—C5—C6—C11.6 (7)N4—C32—C33—C38118.7 (5)
C4—C5—C6—C7179.4 (4)C31—C32—C33—C3861.9 (6)
O1—C1—C6—C5176.1 (4)N4—C32—C33—C3464.9 (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—C7177.2 (4)C32—C33—C34—C35176.3 (5)
N1—N2—C7—C6179.7 (4)C33—C34—C35—C360.3 (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—C8179.2 (3)C36—C37—C38—C330.0 (9)
C5—C6—C7—N2177.0 (4)C34—C33—C38—C370.1 (8)
C1—C6—C7—N21.9 (7)C32—C33—C38—C37176.4 (5)
C5—C6—C7—C83.1 (6)Ni2—O4—C39—N30.1 (6)
C1—C6—C7—C8178.0 (4)Ni2—O4—C39—C40178.9 (3)
N2—C7—C8—C974.7 (6)N4—N3—C39—O40.8 (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—C1372.5 (6)N3—C39—C40—C41166.6 (5)
C13—C8—C9—C101.9 (7)O4—C39—C40—C45169.5 (5)
C7—C8—C9—C10176.1 (5)N3—C39—C40—C4511.5 (8)
C8—C9—C10—C111.0 (8)C45—C40—C41—C420.8 (8)
C9—C10—C11—C120.4 (9)C39—C40—C41—C42177.3 (5)
C10—C11—C12—C130.9 (9)C40—C41—C42—C430.6 (10)
C9—C8—C13—C121.3 (8)C41—C42—C43—C440.5 (11)
C7—C8—C13—C12176.6 (5)C42—C43—C44—C451.2 (10)
C11—C12—C13—C80.1 (9)C43—C44—C45—C400.9 (10)
Ni1—O2—C14—N13.5 (6)C41—C40—C45—C440.1 (9)
Ni1—O2—C14—C15175.5 (3)C39—C40—C45—C44178.0 (5)
N2—N1—C14—O21.3 (6)C50—N6—C46—C470.9 (7)
N2—N1—C14—C15177.7 (4)Ni2—N6—C46—C47177.4 (4)
O2—C14—C15—C16141.4 (5)N6—C46—C47—C480.8 (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—C20144.1 (5)C46—N6—C50—C492.3 (7)
C20—C15—C16—C171.0 (7)Ni2—N6—C50—C49176.0 (4)
C14—C15—C16—C17177.4 (5)C48—C49—C50—N62.1 (8)

Experimental details

Crystal data
Chemical formula[Ni(C20H13BrN2O2)(C5H5N)]
Mr531.01
Crystal system, space groupMonoclinic, P21/c
Temperature (K)295
a, b, c (Å)22.638 (5), 10.628 (2), 19.302 (4)
β (°) 108.597 (4)
V3)4401.5 (16)
Z8
Radiation typeMo Kα
µ (mm1)2.73
Crystal size (mm)0.16 × 0.12 × 0.08
Data collection
DiffractometerBruker APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.670, 0.812
No. of measured, independent and
observed [I > 2σ(I)] reflections
22758, 7792, 4790
Rint0.054
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.120, 1.01
No. of reflections7792
No. of parameters577
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.98, 0.64

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

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

References

First citationAli, H. M., Khamis, N. A. & Yamin, B. M. (2004). Acta Cryst. E60, m1708–m1709.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationCarcelli, M., Mazza, P., Pelizzi, G. & Zani, F. (1995). J. Inorg. Biochem. 57, 43–62.  CrossRef CAS PubMed Web of Science Google Scholar
First citationSalem, A. A. (1998). Microchem. J. 60, 51–66.  Web of Science CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSingh, R. B., Jain, P. & Singh, R. P. (1982). Talanta, 29, 77–84.  CrossRef PubMed CAS Web of Science Google Scholar

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