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Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): m1060.
Published online 2009 August 12. doi:  10.1107/S1600536809030943
PMCID: PMC2969971

{N′-[(E)-(5-Bromo-2-oxidophen­yl)(phenyl)­methyl­ene]-4-chloro­benzo­hydrazidato}pyridine­nickel(II)

Abstract

The asymmetric unit of title complex, [Ni(C20H12BrClN2O2)(C5H5N)], contains one complex with the central Ni atom in a slightly distorted square–planar environment, formed by the tridentate hydrazone and the monodentate pyridine ligands, with N atoms in a trans arrangement about the Ni 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]); Chang et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1060-scheme1.jpg

Experimental

Crystal data

  • [Ni(C20H12BrClN2O2)(C5H5N)]
  • M r = 565.49
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1060-efi1.jpg
  • a = 9.854 (3) Å
  • b = 21.981 (8) Å
  • c = 10.857 (4) Å
  • β = 102.705 (6)°
  • V = 2294.0 (14) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 2.73 mm−1
  • T = 298 K
  • 0.21 × 0.16 × 0.12 mm

Data collection

  • Siemens SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.586, T max = 0.720
  • 11902 measured reflections
  • 4065 independent reflections
  • 3109 reflections with I > 2σ(I)
  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.030
  • wR(F 2) = 0.073
  • S = 1.02
  • 4065 reflections
  • 298 parameters
  • H-atom parameters constrained
  • Δρmax = 0.37 e Å−3
  • Δρmin = −0.40 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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809030943/bh2240sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030943/bh2240Isup2.hkl

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

Acknowledgments

This project was supported by the Postgraduate Foundation of Xi’an Polytechnic University (grant 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 our work on the structural characterization of aroylhydrazone derivatives, the title compound was synthesized and its crystal structure is reported here. The geometric features compare well with those observed in a closely related NiII complex including a methyl group in place of the phenyl group in the hydrazone ligand (Chang et al., 2009).

Experimental

A DMF solution (5 ml) of N'-[(E)-(5-bromo-2-hydroxyphenyl)-(phenyl)methylene]-4-chlorobenzohydrazide (0.25 mmol, 0.108 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 days. A pyridine amount (5 ml) was used to dissolve the precipitate at 330 K. Red block-shaped crystals of the title complex were obtained after one month (yield 30%).

Refinement

H atoms were placed in calculated positions, with C—H bond lengths fixed to 0.93 Å and isotropic displacement parameters computed as Uiso(H) = 1.2Ueq(carrier C).

Figures

Fig. 1.
The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted.

Crystal data

[Ni(C20H12BrClN2O2)(C5H5N)]F(000) = 1136
Mr = 565.49Dx = 1.637 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3944 reflections
a = 9.854 (3) Åθ = 2.3–25.5°
b = 21.981 (8) ŵ = 2.73 mm1
c = 10.857 (4) ÅT = 298 K
β = 102.705 (6)°Block, red
V = 2294.0 (14) Å30.21 × 0.16 × 0.12 mm
Z = 4

Data collection

Siemens SMART CCD area-detector diffractometer4065 independent reflections
Radiation source: fine-focus sealed tube3109 reflections with I > 2σ(I)
graphiteRint = 0.024
[var phi] and ω scansθmax = 25.1°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→11
Tmin = 0.586, Tmax = 0.720k = −26→25
11902 measured reflectionsl = −12→5

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)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0311P)2 + 0.9549P] where P = (Fo2 + 2Fc2)/3
4065 reflections(Δ/σ)max = 0.002
298 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = −0.40 e Å3
0 constraints

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

xyzUiso*/Ueq
Ni10.26454 (3)0.532600 (15)1.11149 (3)0.04069 (11)
Br1−0.09024 (4)0.248039 (14)0.90729 (4)0.07783 (14)
Cl10.75673 (10)0.74454 (4)0.73128 (10)0.0848 (3)
O10.14617 (18)0.47902 (8)1.15713 (16)0.0472 (5)
O20.37690 (18)0.59030 (8)1.06354 (16)0.0458 (4)
N10.2572 (2)0.50057 (9)0.95458 (19)0.0383 (5)
N20.3321 (2)0.53375 (10)0.8816 (2)0.0430 (5)
N30.2890 (2)0.56951 (10)1.2752 (2)0.0448 (5)
C10.0919 (3)0.43111 (12)1.0924 (2)0.0419 (6)
C20.1125 (2)0.41494 (11)0.9716 (2)0.0374 (6)
C30.0546 (3)0.35969 (11)0.9185 (3)0.0431 (6)
H30.06890.34760.84030.052*
C4−0.0217 (3)0.32383 (12)0.9796 (3)0.0492 (7)
C5−0.0490 (3)0.34103 (13)1.0941 (3)0.0545 (7)
H5−0.10420.31691.13350.065*
C60.0061 (3)0.39382 (13)1.1481 (3)0.0521 (7)
H6−0.01350.40571.22460.062*
C70.1913 (2)0.45224 (11)0.9028 (2)0.0367 (6)
C80.1938 (2)0.43598 (11)0.7696 (2)0.0366 (6)
C90.0738 (3)0.44230 (13)0.6775 (3)0.0510 (7)
H9−0.00510.45910.69780.061*
C100.0701 (3)0.42394 (16)0.5556 (3)0.0608 (8)
H10−0.01120.42840.49380.073*
C110.1853 (3)0.39918 (14)0.5251 (3)0.0595 (8)
H110.18190.38570.44330.071*
C120.3056 (3)0.39419 (14)0.6150 (3)0.0571 (8)
H120.38480.37830.59350.069*
C130.3110 (3)0.41244 (12)0.7371 (3)0.0481 (7)
H130.39350.40890.79770.058*
C140.3916 (3)0.57897 (12)0.9492 (2)0.0419 (6)
C150.4824 (3)0.62008 (12)0.8963 (2)0.0428 (6)
C160.5334 (3)0.60263 (13)0.7936 (3)0.0496 (7)
H160.51090.56450.75790.060*
C170.6169 (3)0.64078 (14)0.7431 (3)0.0574 (8)
H170.65020.62870.67310.069*
C180.6507 (3)0.69658 (13)0.7959 (3)0.0551 (8)
C190.6050 (4)0.71440 (15)0.8996 (3)0.0739 (10)
H190.63040.75220.93610.089*
C200.5210 (4)0.67624 (13)0.9501 (3)0.0672 (9)
H200.48980.68831.02120.081*
C210.2964 (3)0.53641 (14)1.3794 (3)0.0527 (7)
H210.29380.49421.37230.063*
C220.3077 (3)0.56172 (16)1.4965 (3)0.0616 (8)
H220.31380.53721.56740.074*
C230.3100 (3)0.62345 (17)1.5074 (3)0.0681 (9)
H230.31580.64181.58560.082*
C240.3034 (3)0.65820 (15)1.4015 (3)0.0662 (9)
H240.30500.70041.40700.079*
C250.2946 (3)0.63000 (13)1.2870 (3)0.0558 (8)
H250.29230.65371.21560.067*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ni10.0429 (2)0.0438 (2)0.03664 (19)−0.00025 (15)0.01135 (14)−0.00238 (15)
Br10.1043 (3)0.0495 (2)0.0882 (3)−0.02548 (18)0.0396 (2)−0.00483 (17)
Cl10.0865 (6)0.0756 (6)0.0996 (7)−0.0186 (5)0.0359 (5)0.0262 (5)
O10.0524 (11)0.0530 (11)0.0399 (10)−0.0067 (9)0.0185 (9)−0.0045 (9)
O20.0524 (11)0.0451 (10)0.0413 (10)−0.0079 (9)0.0134 (8)−0.0051 (8)
N10.0394 (12)0.0400 (12)0.0371 (12)−0.0016 (10)0.0118 (9)0.0003 (10)
N20.0455 (12)0.0440 (12)0.0419 (12)−0.0066 (11)0.0147 (10)−0.0010 (11)
N30.0419 (13)0.0511 (14)0.0429 (14)0.0027 (10)0.0126 (10)−0.0044 (11)
C10.0404 (15)0.0457 (15)0.0405 (16)0.0022 (12)0.0107 (12)0.0083 (13)
C20.0354 (13)0.0393 (14)0.0386 (15)0.0033 (11)0.0101 (11)0.0051 (12)
C30.0475 (16)0.0414 (15)0.0426 (15)0.0019 (12)0.0143 (12)0.0040 (12)
C40.0529 (17)0.0413 (15)0.0549 (18)−0.0066 (13)0.0149 (14)0.0048 (13)
C50.0594 (18)0.0567 (18)0.0509 (18)−0.0104 (15)0.0194 (15)0.0132 (15)
C60.0548 (18)0.0645 (19)0.0399 (16)−0.0045 (15)0.0168 (13)0.0040 (14)
C70.0348 (13)0.0391 (14)0.0374 (14)0.0037 (11)0.0106 (11)0.0023 (11)
C80.0389 (14)0.0355 (13)0.0373 (14)−0.0051 (11)0.0127 (12)−0.0009 (11)
C90.0389 (16)0.0704 (19)0.0456 (17)0.0044 (14)0.0131 (13)−0.0035 (14)
C100.0491 (18)0.094 (2)0.0395 (17)−0.0009 (16)0.0092 (14)−0.0041 (16)
C110.063 (2)0.076 (2)0.0442 (17)−0.0075 (17)0.0231 (15)−0.0117 (15)
C120.0510 (18)0.067 (2)0.0596 (19)0.0080 (15)0.0262 (16)−0.0087 (16)
C130.0399 (15)0.0561 (17)0.0493 (17)0.0040 (13)0.0122 (13)−0.0042 (14)
C140.0420 (15)0.0422 (15)0.0422 (16)0.0016 (12)0.0106 (12)0.0002 (13)
C150.0435 (16)0.0406 (15)0.0433 (16)0.0001 (12)0.0076 (12)0.0027 (12)
C160.0477 (16)0.0490 (16)0.0542 (18)−0.0042 (13)0.0157 (14)−0.0065 (14)
C170.0555 (19)0.064 (2)0.0592 (19)−0.0024 (15)0.0262 (15)0.0005 (16)
C180.0520 (17)0.0527 (18)0.061 (2)−0.0030 (14)0.0141 (15)0.0148 (15)
C190.106 (3)0.0446 (18)0.077 (2)−0.0216 (18)0.033 (2)−0.0047 (17)
C200.098 (3)0.0495 (18)0.064 (2)−0.0193 (17)0.0373 (19)−0.0090 (16)
C210.0522 (17)0.0596 (18)0.0451 (17)0.0029 (15)0.0081 (13)−0.0012 (15)
C220.062 (2)0.079 (2)0.0418 (18)0.0070 (17)0.0070 (15)−0.0043 (16)
C230.064 (2)0.090 (3)0.048 (2)0.0167 (18)0.0085 (16)−0.0215 (19)
C240.071 (2)0.0582 (19)0.070 (2)0.0103 (17)0.0174 (18)−0.0202 (18)
C250.0603 (19)0.0534 (19)0.0555 (19)0.0071 (14)0.0167 (15)−0.0066 (15)

Geometric parameters (Å, °)

Ni1—O11.8020 (18)C10—C111.364 (4)
Ni1—N11.830 (2)C10—H100.9300
Ni1—O21.8327 (18)C11—C121.364 (4)
Ni1—N31.920 (2)C11—H110.9300
Br1—C41.901 (3)C12—C131.374 (4)
Cl1—C181.737 (3)C12—H120.9300
O1—C11.313 (3)C13—H130.9300
O2—C141.305 (3)C14—C151.474 (4)
N1—C71.306 (3)C15—C161.375 (4)
N1—N21.400 (3)C15—C201.383 (4)
N2—C141.297 (3)C16—C171.371 (4)
N3—C211.333 (3)C16—H160.9300
N3—C251.336 (4)C17—C181.364 (4)
C1—C61.406 (4)C17—H170.9300
C1—C21.416 (3)C18—C191.359 (4)
C2—C31.410 (3)C19—C201.375 (4)
C2—C71.446 (3)C19—H190.9300
C3—C41.358 (4)C20—H200.9300
C3—H30.9300C21—C221.370 (4)
C4—C51.381 (4)C21—H210.9300
C5—C61.359 (4)C22—C231.362 (4)
C5—H50.9300C22—H220.9300
C6—H60.9300C23—C241.370 (4)
C7—C81.494 (3)C23—H230.9300
C8—C91.378 (4)C24—C251.375 (4)
C8—C131.381 (3)C24—H240.9300
C9—C101.377 (4)C25—H250.9300
C9—H90.9300
O1—Ni1—N196.26 (9)C10—C11—C12119.9 (3)
O1—Ni1—O2176.73 (8)C10—C11—H11120.1
N1—Ni1—O284.52 (8)C12—C11—H11120.1
O1—Ni1—N388.78 (9)C11—C12—C13120.6 (3)
N1—Ni1—N3174.55 (9)C11—C12—H12119.7
O2—Ni1—N390.56 (9)C13—C12—H12119.7
C1—O1—Ni1126.12 (16)C12—C13—C8119.9 (3)
C14—O2—Ni1109.80 (16)C12—C13—H13120.0
C7—N1—N2117.0 (2)C8—C13—H13120.0
C7—N1—Ni1128.91 (17)N2—C14—O2123.6 (2)
N2—N1—Ni1114.09 (15)N2—C14—C15119.2 (2)
C14—N2—N1108.0 (2)O2—C14—C15117.2 (2)
C21—N3—C25118.0 (2)C16—C15—C20118.4 (3)
C21—N3—Ni1121.80 (19)C16—C15—C14120.4 (2)
C25—N3—Ni1120.2 (2)C20—C15—C14121.1 (3)
O1—C1—C6116.8 (2)C17—C16—C15120.8 (3)
O1—C1—C2124.9 (2)C17—C16—H16119.6
C6—C1—C2118.3 (2)C15—C16—H16119.6
C3—C2—C1117.9 (2)C18—C17—C16119.6 (3)
C3—C2—C7119.5 (2)C18—C17—H17120.2
C1—C2—C7122.6 (2)C16—C17—H17120.2
C4—C3—C2121.2 (2)C19—C18—C17120.8 (3)
C4—C3—H3119.4C19—C18—Cl1119.9 (2)
C2—C3—H3119.4C17—C18—Cl1119.3 (2)
C3—C4—C5121.2 (3)C18—C19—C20119.6 (3)
C3—C4—Br1119.4 (2)C18—C19—H19120.2
C5—C4—Br1119.3 (2)C20—C19—H19120.2
C6—C5—C4118.9 (3)C19—C20—C15120.7 (3)
C6—C5—H5120.5C19—C20—H20119.7
C4—C5—H5120.5C15—C20—H20119.7
C5—C6—C1122.2 (3)N3—C21—C22122.9 (3)
C5—C6—H6118.9N3—C21—H21118.5
C1—C6—H6118.9C22—C21—H21118.5
N1—C7—C2120.8 (2)C23—C22—C21118.8 (3)
N1—C7—C8119.9 (2)C23—C22—H22120.6
C2—C7—C8119.3 (2)C21—C22—H22120.6
C9—C8—C13119.0 (2)C22—C23—C24119.1 (3)
C9—C8—C7118.9 (2)C22—C23—H23120.4
C13—C8—C7122.0 (2)C24—C23—H23120.4
C10—C9—C8120.4 (3)C23—C24—C25119.3 (3)
C10—C9—H9119.8C23—C24—H24120.3
C8—C9—H9119.8C25—C24—H24120.3
C11—C10—C9120.2 (3)N3—C25—C24121.9 (3)
C11—C10—H10119.9N3—C25—H25119.1
C9—C10—H10119.9C24—C25—H25119.1
N1—Ni1—O1—C15.7 (2)C2—C7—C8—C968.7 (3)
N3—Ni1—O1—C1−172.2 (2)N1—C7—C8—C1373.1 (3)
N1—Ni1—O2—C140.11 (17)C2—C7—C8—C13−108.6 (3)
N3—Ni1—O2—C14177.75 (17)C13—C8—C9—C101.6 (4)
O1—Ni1—N1—C7−3.5 (2)C7—C8—C9—C10−175.7 (3)
O2—Ni1—N1—C7179.7 (2)C8—C9—C10—C110.2 (5)
O1—Ni1—N1—N2175.72 (16)C9—C10—C11—C12−1.9 (5)
O2—Ni1—N1—N2−1.09 (16)C10—C11—C12—C131.7 (5)
C7—N1—N2—C14−178.9 (2)C11—C12—C13—C80.1 (4)
Ni1—N1—N2—C141.8 (2)C9—C8—C13—C12−1.8 (4)
O1—Ni1—N3—C2139.0 (2)C7—C8—C13—C12175.5 (2)
O2—Ni1—N3—C21−144.2 (2)N1—N2—C14—O2−1.9 (3)
O1—Ni1—N3—C25−138.8 (2)N1—N2—C14—C15177.5 (2)
O2—Ni1—N3—C2538.0 (2)Ni1—O2—C14—N21.1 (3)
Ni1—O1—C1—C6177.42 (18)Ni1—O2—C14—C15−178.35 (17)
Ni1—O1—C1—C2−3.2 (4)N2—C14—C15—C16−17.2 (4)
O1—C1—C2—C3175.7 (2)O2—C14—C15—C16162.2 (2)
C6—C1—C2—C3−4.9 (4)N2—C14—C15—C20164.3 (3)
O1—C1—C2—C7−3.5 (4)O2—C14—C15—C20−16.3 (4)
C6—C1—C2—C7175.9 (2)C20—C15—C16—C17−2.1 (4)
C1—C2—C3—C41.8 (4)C14—C15—C16—C17179.4 (3)
C7—C2—C3—C4−179.1 (2)C15—C16—C17—C180.5 (5)
C2—C3—C4—C52.0 (4)C16—C17—C18—C191.3 (5)
C2—C3—C4—Br1−177.16 (19)C16—C17—C18—Cl1179.9 (2)
C3—C4—C5—C6−2.4 (4)C17—C18—C19—C20−1.5 (5)
Br1—C4—C5—C6176.8 (2)Cl1—C18—C19—C20179.9 (3)
C4—C5—C6—C1−1.0 (4)C18—C19—C20—C15−0.1 (5)
O1—C1—C6—C5−175.9 (2)C16—C15—C20—C191.9 (5)
C2—C1—C6—C54.7 (4)C14—C15—C20—C19−179.6 (3)
N2—N1—C7—C2179.4 (2)C25—N3—C21—C220.8 (4)
Ni1—N1—C7—C2−1.4 (3)Ni1—N3—C21—C22−177.1 (2)
N2—N1—C7—C8−2.3 (3)N3—C21—C22—C230.8 (5)
Ni1—N1—C7—C8176.90 (17)C21—C22—C23—C24−1.2 (5)
C3—C2—C7—N1−173.4 (2)C22—C23—C24—C250.1 (5)
C1—C2—C7—N15.7 (4)C21—N3—C25—C24−1.9 (4)
C3—C2—C7—C88.3 (3)Ni1—N3—C25—C24176.0 (2)
C1—C2—C7—C8−172.6 (2)C23—C24—C25—N31.5 (5)
N1—C7—C8—C9−109.7 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2240).

References

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