Acta Cryst. (2009). E65, m1060 [ doi:10.1107/S1600536809030943 ]
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.
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%).
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).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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).
![[Figure 1]](./bh2240fig1thm.gif)
| 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. |
| [Ni(C20H12BrClN2O2)(C5H5N)] | F(000) = 1136 |
| Mr = 565.49 | Dx = 1.637 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 3944 reflections |
| a = 9.854 (3) Å | θ = 2.3–25.5° |
| b = 21.981 (8) Å | µ = 2.73 mm−1 |
| c = 10.857 (4) Å | T = 298 K |
| β = 102.705 (6)° | Block, red |
| V = 2294.0 (14) Å3 | 0.21 × 0.16 × 0.12 mm |
| Z = 4 |
| Siemens SMART CCD area-detector diffractometer | 4065 independent reflections |
| Radiation source: fine-focus sealed tube | 3109 reflections with I > 2σ(I) |
| graphite | Rint = 0.024 |
| φ and ω scans | θmax = 25.1°, θmin = 1.9° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
| Tmin = 0.586, Tmax = 0.720 | k = −26→25 |
| 11902 measured reflections | l = −12→5 |
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.073 | H-atom parameters constrained |
| S = 1.02 | w = 1/[σ2(Fo2) + (0.0311P)2 + 0.9549P] where P = (Fo2 + 2Fc2)/3 |
| 4065 reflections | (Δ/σ)max = 0.002 |
| 298 parameters | Δρmax = 0.37 e Å−3 |
| 0 restraints | Δρmin = −0.40 e Å−3 |
| 0 constraints |
| [Ni(C20H12BrClN2O2)(C5H5N)] | V = 2294.0 (14) Å3 |
| Mr = 565.49 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 9.854 (3) Å | µ = 2.73 mm−1 |
| b = 21.981 (8) Å | T = 298 K |
| c = 10.857 (4) Å | 0.21 × 0.16 × 0.12 mm |
| β = 102.705 (6)° |
| Siemens SMART CCD area-detector diffractometer | 4065 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3109 reflections with I > 2σ(I) |
| Tmin = 0.586, Tmax = 0.720 | Rint = 0.024 |
| 11902 measured reflections | θmax = 25.1° |
| R[F2 > 2σ(F2)] = 0.030 | H-atom parameters constrained |
| wR(F2) = 0.073 | Δρmax = 0.37 e Å−3 |
| S = 1.02 | Δρmin = −0.40 e Å−3 |
| 4065 reflections | Absolute structure: ? |
| 298 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
| x | y | z | Uiso*/Ueq | ||
| Ni1 | 0.26454 (3) | 0.532600 (15) | 1.11149 (3) | 0.04069 (11) | |
| Br1 | −0.09024 (4) | 0.248039 (14) | 0.90729 (4) | 0.07783 (14) | |
| Cl1 | 0.75673 (10) | 0.74454 (4) | 0.73128 (10) | 0.0848 (3) | |
| O1 | 0.14617 (18) | 0.47902 (8) | 1.15713 (16) | 0.0472 (5) | |
| O2 | 0.37690 (18) | 0.59030 (8) | 1.06354 (16) | 0.0458 (4) | |
| N1 | 0.2572 (2) | 0.50057 (9) | 0.95458 (19) | 0.0383 (5) | |
| N2 | 0.3321 (2) | 0.53375 (10) | 0.8816 (2) | 0.0430 (5) | |
| N3 | 0.2890 (2) | 0.56951 (10) | 1.2752 (2) | 0.0448 (5) | |
| C1 | 0.0919 (3) | 0.43111 (12) | 1.0924 (2) | 0.0419 (6) | |
| C2 | 0.1125 (2) | 0.41494 (11) | 0.9716 (2) | 0.0374 (6) | |
| C3 | 0.0546 (3) | 0.35969 (11) | 0.9185 (3) | 0.0431 (6) | |
| H3 | 0.0689 | 0.3476 | 0.8403 | 0.052* | |
| 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 | −0.1042 | 0.3169 | 1.1335 | 0.065* | |
| C6 | 0.0061 (3) | 0.39382 (13) | 1.1481 (3) | 0.0521 (7) | |
| H6 | −0.0135 | 0.4057 | 1.2246 | 0.062* | |
| C7 | 0.1913 (2) | 0.45224 (11) | 0.9028 (2) | 0.0367 (6) | |
| C8 | 0.1938 (2) | 0.43598 (11) | 0.7696 (2) | 0.0366 (6) | |
| C9 | 0.0738 (3) | 0.44230 (13) | 0.6775 (3) | 0.0510 (7) | |
| H9 | −0.0051 | 0.4591 | 0.6978 | 0.061* | |
| C10 | 0.0701 (3) | 0.42394 (16) | 0.5556 (3) | 0.0608 (8) | |
| H10 | −0.0112 | 0.4284 | 0.4938 | 0.073* | |
| C11 | 0.1853 (3) | 0.39918 (14) | 0.5251 (3) | 0.0595 (8) | |
| H11 | 0.1819 | 0.3857 | 0.4433 | 0.071* | |
| C12 | 0.3056 (3) | 0.39419 (14) | 0.6150 (3) | 0.0571 (8) | |
| H12 | 0.3848 | 0.3783 | 0.5935 | 0.069* | |
| C13 | 0.3110 (3) | 0.41244 (12) | 0.7371 (3) | 0.0481 (7) | |
| H13 | 0.3935 | 0.4089 | 0.7977 | 0.058* | |
| C14 | 0.3916 (3) | 0.57897 (12) | 0.9492 (2) | 0.0419 (6) | |
| C15 | 0.4824 (3) | 0.62008 (12) | 0.8963 (2) | 0.0428 (6) | |
| C16 | 0.5334 (3) | 0.60263 (13) | 0.7936 (3) | 0.0496 (7) | |
| H16 | 0.5109 | 0.5645 | 0.7579 | 0.060* | |
| C17 | 0.6169 (3) | 0.64078 (14) | 0.7431 (3) | 0.0574 (8) | |
| H17 | 0.6502 | 0.6287 | 0.6731 | 0.069* | |
| C18 | 0.6507 (3) | 0.69658 (13) | 0.7959 (3) | 0.0551 (8) | |
| C19 | 0.6050 (4) | 0.71440 (15) | 0.8996 (3) | 0.0739 (10) | |
| H19 | 0.6304 | 0.7522 | 0.9361 | 0.089* | |
| C20 | 0.5210 (4) | 0.67624 (13) | 0.9501 (3) | 0.0672 (9) | |
| H20 | 0.4898 | 0.6883 | 1.0212 | 0.081* | |
| C21 | 0.2964 (3) | 0.53641 (14) | 1.3794 (3) | 0.0527 (7) | |
| H21 | 0.2938 | 0.4942 | 1.3723 | 0.063* | |
| C22 | 0.3077 (3) | 0.56172 (16) | 1.4965 (3) | 0.0616 (8) | |
| H22 | 0.3138 | 0.5372 | 1.5674 | 0.074* | |
| C23 | 0.3100 (3) | 0.62345 (17) | 1.5074 (3) | 0.0681 (9) | |
| H23 | 0.3158 | 0.6418 | 1.5856 | 0.082* | |
| C24 | 0.3034 (3) | 0.65820 (15) | 1.4015 (3) | 0.0662 (9) | |
| H24 | 0.3050 | 0.7004 | 1.4070 | 0.079* | |
| C25 | 0.2946 (3) | 0.63000 (13) | 1.2870 (3) | 0.0558 (8) | |
| H25 | 0.2923 | 0.6537 | 1.2156 | 0.067* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Ni1 | 0.0429 (2) | 0.0438 (2) | 0.03664 (19) | −0.00025 (15) | 0.01135 (14) | −0.00238 (15) |
| Br1 | 0.1043 (3) | 0.0495 (2) | 0.0882 (3) | −0.02548 (18) | 0.0396 (2) | −0.00483 (17) |
| Cl1 | 0.0865 (6) | 0.0756 (6) | 0.0996 (7) | −0.0186 (5) | 0.0359 (5) | 0.0262 (5) |
| O1 | 0.0524 (11) | 0.0530 (11) | 0.0399 (10) | −0.0067 (9) | 0.0185 (9) | −0.0045 (9) |
| O2 | 0.0524 (11) | 0.0451 (10) | 0.0413 (10) | −0.0079 (9) | 0.0134 (8) | −0.0051 (8) |
| N1 | 0.0394 (12) | 0.0400 (12) | 0.0371 (12) | −0.0016 (10) | 0.0118 (9) | 0.0003 (10) |
| N2 | 0.0455 (12) | 0.0440 (12) | 0.0419 (12) | −0.0066 (11) | 0.0147 (10) | −0.0010 (11) |
| N3 | 0.0419 (13) | 0.0511 (14) | 0.0429 (14) | 0.0027 (10) | 0.0126 (10) | −0.0044 (11) |
| C1 | 0.0404 (15) | 0.0457 (15) | 0.0405 (16) | 0.0022 (12) | 0.0107 (12) | 0.0083 (13) |
| C2 | 0.0354 (13) | 0.0393 (14) | 0.0386 (15) | 0.0033 (11) | 0.0101 (11) | 0.0051 (12) |
| C3 | 0.0475 (16) | 0.0414 (15) | 0.0426 (15) | 0.0019 (12) | 0.0143 (12) | 0.0040 (12) |
| C4 | 0.0529 (17) | 0.0413 (15) | 0.0549 (18) | −0.0066 (13) | 0.0149 (14) | 0.0048 (13) |
| C5 | 0.0594 (18) | 0.0567 (18) | 0.0509 (18) | −0.0104 (15) | 0.0194 (15) | 0.0132 (15) |
| C6 | 0.0548 (18) | 0.0645 (19) | 0.0399 (16) | −0.0045 (15) | 0.0168 (13) | 0.0040 (14) |
| C7 | 0.0348 (13) | 0.0391 (14) | 0.0374 (14) | 0.0037 (11) | 0.0106 (11) | 0.0023 (11) |
| C8 | 0.0389 (14) | 0.0355 (13) | 0.0373 (14) | −0.0051 (11) | 0.0127 (12) | −0.0009 (11) |
| C9 | 0.0389 (16) | 0.0704 (19) | 0.0456 (17) | 0.0044 (14) | 0.0131 (13) | −0.0035 (14) |
| C10 | 0.0491 (18) | 0.094 (2) | 0.0395 (17) | −0.0009 (16) | 0.0092 (14) | −0.0041 (16) |
| C11 | 0.063 (2) | 0.076 (2) | 0.0442 (17) | −0.0075 (17) | 0.0231 (15) | −0.0117 (15) |
| C12 | 0.0510 (18) | 0.067 (2) | 0.0596 (19) | 0.0080 (15) | 0.0262 (16) | −0.0087 (16) |
| C13 | 0.0399 (15) | 0.0561 (17) | 0.0493 (17) | 0.0040 (13) | 0.0122 (13) | −0.0042 (14) |
| C14 | 0.0420 (15) | 0.0422 (15) | 0.0422 (16) | 0.0016 (12) | 0.0106 (12) | 0.0002 (13) |
| C15 | 0.0435 (16) | 0.0406 (15) | 0.0433 (16) | 0.0001 (12) | 0.0076 (12) | 0.0027 (12) |
| C16 | 0.0477 (16) | 0.0490 (16) | 0.0542 (18) | −0.0042 (13) | 0.0157 (14) | −0.0065 (14) |
| C17 | 0.0555 (19) | 0.064 (2) | 0.0592 (19) | −0.0024 (15) | 0.0262 (15) | 0.0005 (16) |
| C18 | 0.0520 (17) | 0.0527 (18) | 0.061 (2) | −0.0030 (14) | 0.0141 (15) | 0.0148 (15) |
| C19 | 0.106 (3) | 0.0446 (18) | 0.077 (2) | −0.0216 (18) | 0.033 (2) | −0.0047 (17) |
| C20 | 0.098 (3) | 0.0495 (18) | 0.064 (2) | −0.0193 (17) | 0.0373 (19) | −0.0090 (16) |
| C21 | 0.0522 (17) | 0.0596 (18) | 0.0451 (17) | 0.0029 (15) | 0.0081 (13) | −0.0012 (15) |
| C22 | 0.062 (2) | 0.079 (2) | 0.0418 (18) | 0.0070 (17) | 0.0070 (15) | −0.0043 (16) |
| C23 | 0.064 (2) | 0.090 (3) | 0.048 (2) | 0.0167 (18) | 0.0085 (16) | −0.0215 (19) |
| C24 | 0.071 (2) | 0.0582 (19) | 0.070 (2) | 0.0103 (17) | 0.0174 (18) | −0.0202 (18) |
| C25 | 0.0603 (19) | 0.0534 (19) | 0.0555 (19) | 0.0071 (14) | 0.0167 (15) | −0.0066 (15) |
| Ni1—O1 | 1.8020 (18) | C10—C11 | 1.364 (4) |
| Ni1—N1 | 1.830 (2) | C10—H10 | 0.9300 |
| Ni1—O2 | 1.8327 (18) | C11—C12 | 1.364 (4) |
| Ni1—N3 | 1.920 (2) | C11—H11 | 0.9300 |
| Br1—C4 | 1.901 (3) | C12—C13 | 1.374 (4) |
| Cl1—C18 | 1.737 (3) | C12—H12 | 0.9300 |
| O1—C1 | 1.313 (3) | C13—H13 | 0.9300 |
| O2—C14 | 1.305 (3) | C14—C15 | 1.474 (4) |
| N1—C7 | 1.306 (3) | C15—C16 | 1.375 (4) |
| N1—N2 | 1.400 (3) | C15—C20 | 1.383 (4) |
| N2—C14 | 1.297 (3) | C16—C17 | 1.371 (4) |
| N3—C21 | 1.333 (3) | C16—H16 | 0.9300 |
| N3—C25 | 1.336 (4) | C17—C18 | 1.364 (4) |
| C1—C6 | 1.406 (4) | C17—H17 | 0.9300 |
| C1—C2 | 1.416 (3) | C18—C19 | 1.359 (4) |
| C2—C3 | 1.410 (3) | C19—C20 | 1.375 (4) |
| C2—C7 | 1.446 (3) | C19—H19 | 0.9300 |
| C3—C4 | 1.358 (4) | C20—H20 | 0.9300 |
| C3—H3 | 0.9300 | C21—C22 | 1.370 (4) |
| C4—C5 | 1.381 (4) | C21—H21 | 0.9300 |
| C5—C6 | 1.359 (4) | C22—C23 | 1.362 (4) |
| C5—H5 | 0.9300 | C22—H22 | 0.9300 |
| C6—H6 | 0.9300 | C23—C24 | 1.370 (4) |
| C7—C8 | 1.494 (3) | C23—H23 | 0.9300 |
| C8—C9 | 1.378 (4) | C24—C25 | 1.375 (4) |
| C8—C13 | 1.381 (3) | C24—H24 | 0.9300 |
| C9—C10 | 1.377 (4) | C25—H25 | 0.9300 |
| C9—H9 | 0.9300 | ||
| O1—Ni1—N1 | 96.26 (9) | C10—C11—C12 | 119.9 (3) |
| O1—Ni1—O2 | 176.73 (8) | C10—C11—H11 | 120.1 |
| N1—Ni1—O2 | 84.52 (8) | C12—C11—H11 | 120.1 |
| O1—Ni1—N3 | 88.78 (9) | C11—C12—C13 | 120.6 (3) |
| N1—Ni1—N3 | 174.55 (9) | C11—C12—H12 | 119.7 |
| O2—Ni1—N3 | 90.56 (9) | C13—C12—H12 | 119.7 |
| C1—O1—Ni1 | 126.12 (16) | C12—C13—C8 | 119.9 (3) |
| C14—O2—Ni1 | 109.80 (16) | C12—C13—H13 | 120.0 |
| C7—N1—N2 | 117.0 (2) | C8—C13—H13 | 120.0 |
| C7—N1—Ni1 | 128.91 (17) | N2—C14—O2 | 123.6 (2) |
| N2—N1—Ni1 | 114.09 (15) | N2—C14—C15 | 119.2 (2) |
| C14—N2—N1 | 108.0 (2) | O2—C14—C15 | 117.2 (2) |
| C21—N3—C25 | 118.0 (2) | C16—C15—C20 | 118.4 (3) |
| C21—N3—Ni1 | 121.80 (19) | C16—C15—C14 | 120.4 (2) |
| C25—N3—Ni1 | 120.2 (2) | C20—C15—C14 | 121.1 (3) |
| O1—C1—C6 | 116.8 (2) | C17—C16—C15 | 120.8 (3) |
| O1—C1—C2 | 124.9 (2) | C17—C16—H16 | 119.6 |
| C6—C1—C2 | 118.3 (2) | C15—C16—H16 | 119.6 |
| C3—C2—C1 | 117.9 (2) | C18—C17—C16 | 119.6 (3) |
| C3—C2—C7 | 119.5 (2) | C18—C17—H17 | 120.2 |
| C1—C2—C7 | 122.6 (2) | C16—C17—H17 | 120.2 |
| C4—C3—C2 | 121.2 (2) | C19—C18—C17 | 120.8 (3) |
| C4—C3—H3 | 119.4 | C19—C18—Cl1 | 119.9 (2) |
| C2—C3—H3 | 119.4 | C17—C18—Cl1 | 119.3 (2) |
| C3—C4—C5 | 121.2 (3) | C18—C19—C20 | 119.6 (3) |
| C3—C4—Br1 | 119.4 (2) | C18—C19—H19 | 120.2 |
| C5—C4—Br1 | 119.3 (2) | C20—C19—H19 | 120.2 |
| C6—C5—C4 | 118.9 (3) | C19—C20—C15 | 120.7 (3) |
| C6—C5—H5 | 120.5 | C19—C20—H20 | 119.7 |
| C4—C5—H5 | 120.5 | C15—C20—H20 | 119.7 |
| C5—C6—C1 | 122.2 (3) | N3—C21—C22 | 122.9 (3) |
| C5—C6—H6 | 118.9 | N3—C21—H21 | 118.5 |
| C1—C6—H6 | 118.9 | C22—C21—H21 | 118.5 |
| N1—C7—C2 | 120.8 (2) | C23—C22—C21 | 118.8 (3) |
| N1—C7—C8 | 119.9 (2) | C23—C22—H22 | 120.6 |
| C2—C7—C8 | 119.3 (2) | C21—C22—H22 | 120.6 |
| C9—C8—C13 | 119.0 (2) | C22—C23—C24 | 119.1 (3) |
| C9—C8—C7 | 118.9 (2) | C22—C23—H23 | 120.4 |
| C13—C8—C7 | 122.0 (2) | C24—C23—H23 | 120.4 |
| C10—C9—C8 | 120.4 (3) | C23—C24—C25 | 119.3 (3) |
| C10—C9—H9 | 119.8 | C23—C24—H24 | 120.3 |
| C8—C9—H9 | 119.8 | C25—C24—H24 | 120.3 |
| C11—C10—C9 | 120.2 (3) | N3—C25—C24 | 121.9 (3) |
| C11—C10—H10 | 119.9 | N3—C25—H25 | 119.1 |
| C9—C10—H10 | 119.9 | C24—C25—H25 | 119.1 |
| N1—Ni1—O1—C1 | 5.7 (2) | C2—C7—C8—C9 | 68.7 (3) |
| N3—Ni1—O1—C1 | −172.2 (2) | N1—C7—C8—C13 | 73.1 (3) |
| N1—Ni1—O2—C14 | 0.11 (17) | C2—C7—C8—C13 | −108.6 (3) |
| N3—Ni1—O2—C14 | 177.75 (17) | C13—C8—C9—C10 | 1.6 (4) |
| O1—Ni1—N1—C7 | −3.5 (2) | C7—C8—C9—C10 | −175.7 (3) |
| O2—Ni1—N1—C7 | 179.7 (2) | C8—C9—C10—C11 | 0.2 (5) |
| O1—Ni1—N1—N2 | 175.72 (16) | C9—C10—C11—C12 | −1.9 (5) |
| O2—Ni1—N1—N2 | −1.09 (16) | C10—C11—C12—C13 | 1.7 (5) |
| C7—N1—N2—C14 | −178.9 (2) | C11—C12—C13—C8 | 0.1 (4) |
| Ni1—N1—N2—C14 | 1.8 (2) | C9—C8—C13—C12 | −1.8 (4) |
| O1—Ni1—N3—C21 | 39.0 (2) | C7—C8—C13—C12 | 175.5 (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—C15 | 177.5 (2) |
| O2—Ni1—N3—C25 | 38.0 (2) | Ni1—O2—C14—N2 | 1.1 (3) |
| Ni1—O1—C1—C6 | 177.42 (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—C3 | 175.7 (2) | O2—C14—C15—C16 | 162.2 (2) |
| C6—C1—C2—C3 | −4.9 (4) | N2—C14—C15—C20 | 164.3 (3) |
| O1—C1—C2—C7 | −3.5 (4) | O2—C14—C15—C20 | −16.3 (4) |
| C6—C1—C2—C7 | 175.9 (2) | C20—C15—C16—C17 | −2.1 (4) |
| C1—C2—C3—C4 | 1.8 (4) | C14—C15—C16—C17 | 179.4 (3) |
| C7—C2—C3—C4 | −179.1 (2) | C15—C16—C17—C18 | 0.5 (5) |
| C2—C3—C4—C5 | 2.0 (4) | C16—C17—C18—C19 | 1.3 (5) |
| C2—C3—C4—Br1 | −177.16 (19) | C16—C17—C18—Cl1 | 179.9 (2) |
| C3—C4—C5—C6 | −2.4 (4) | C17—C18—C19—C20 | −1.5 (5) |
| Br1—C4—C5—C6 | 176.8 (2) | Cl1—C18—C19—C20 | 179.9 (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—C19 | 1.9 (5) |
| C2—C1—C6—C5 | 4.7 (4) | C14—C15—C20—C19 | −179.6 (3) |
| N2—N1—C7—C2 | 179.4 (2) | C25—N3—C21—C22 | 0.8 (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—C23 | 0.8 (5) |
| Ni1—N1—C7—C8 | 176.90 (17) | C21—C22—C23—C24 | −1.2 (5) |
| C3—C2—C7—N1 | −173.4 (2) | C22—C23—C24—C25 | 0.1 (5) |
| C1—C2—C7—N1 | 5.7 (4) | C21—N3—C25—C24 | −1.9 (4) |
| C3—C2—C7—C8 | 8.3 (3) | Ni1—N3—C25—C24 | 176.0 (2) |
| C1—C2—C7—C8 | −172.6 (2) | C23—C24—C25—N3 | 1.5 (5) |
| N1—C7—C8—C9 | −109.7 (3) |
This project was supported by the Postgraduate Foundation of Xi'an Polytechnic University (grant No. Y05–2–09).
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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).