Acta Cryst. (2010). E66, m360 [ doi:10.1107/S1600536810007373 ]
In the title Schiff base complex, [Ni(C27H24N2O2)], the NiII atom shows a slightly distorted square-planar geometry. The dihedral angle between the mean planes of the two aromatic rings is 6.16 (6)°. In the crystal, pairs of intermolecular weak C-H
O hydrogen bonds link neighboring molecules into a chain along the a axis. The crystal structure is further stabilized by two intermolecular ![[pi]](/logos/entities/pi_rmgif.gif)
- interactions with centroid-centroid distances of 3.7252 (13) and 3.8323 (13) Å.
The title compound was synthesized by adding bis(naphthaldiminato)-2,3- propanediamine (2 mmol) to a solution of NiCl2. 6 H2O (2 mmol) in ethanol (30 ml). The mixture was refluxed with stirring for half an hour. The resultant red solution was filtered. Red single crystals of the title compound suitable for X-ray structure determination were recrystallized from ethanol by slow evaporation of the solvents at room temperature over several days.
All hydrogen atoms were positioned geometrically with C-H = 0.93-0.97 Å and included in a riding model approximation with Uiso (H) = 1.2 Ueq (C).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
![[Figure 1]](./bq2198fig1thm.gif)
| Fig. 1. The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering. |
![[Figure 2]](./bq2198fig2thm.gif)
| Fig. 2. The packing diagram of the title compound, showing a 1-D infinite chain along the a-axis by the intermolecular C—H···O interactions. The intermolecular h-bonds are shown as dashed lines. |
| [Ni(C27H24N2O2)] | Z = 2 |
| Mr = 467.19 | F(000) = 488 |
| Triclinic, P1 | Dx = 1.442 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 7.5016 (2) Å | Cell parameters from 7107 reflections |
| b = 11.3583 (3) Å | θ = 2.4–28.2° |
| c = 13.0173 (3) Å | µ = 0.93 mm−1 |
| α = 87.846 (2)° | T = 296 K |
| β = 89.496 (1)° | Block, red |
| γ = 76.196 (1)° | 0.45 × 0.23 × 0.12 mm |
| V = 1076.35 (5) Å3 |
| Bruker SMART APEXII CCD area-detector diffractometer | 5293 independent reflections |
| Radiation source: fine-focus sealed tube | 3802 reflections with I > 2σ(I) |
| graphite | Rint = 0.034 |
| φ and ω scans | θmax = 28.3°, θmin = 2.5° |
| Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −9→10 |
| Tmin = 0.680, Tmax = 0.897 | k = −15→15 |
| 23454 measured reflections | l = −17→17 |
| 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)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.085 | H-atom parameters constrained |
| S = 1.02 | w = 1/[σ2(Fo2) + (0.0358P)2 + 0.2515P] where P = (Fo2 + 2Fc2)/3 |
| 5293 reflections | (Δ/σ)max = 0.002 |
| 289 parameters | Δρmax = 0.23 e Å−3 |
| 0 restraints | Δρmin = −0.28 e Å−3 |
| [Ni(C27H24N2O2)] | γ = 76.196 (1)° |
| Mr = 467.19 | V = 1076.35 (5) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 7.5016 (2) Å | Mo Kα radiation |
| b = 11.3583 (3) Å | µ = 0.93 mm−1 |
| c = 13.0173 (3) Å | T = 296 K |
| α = 87.846 (2)° | 0.45 × 0.23 × 0.12 mm |
| β = 89.496 (1)° |
| Bruker SMART APEXII CCD area-detector diffractometer | 5293 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2005) | 3802 reflections with I > 2σ(I) |
| Tmin = 0.680, Tmax = 0.897 | Rint = 0.034 |
| 23454 measured reflections | θmax = 28.3° |
| R[F2 > 2σ(F2)] = 0.033 | H-atom parameters constrained |
| wR(F2) = 0.085 | Δρmax = 0.23 e Å−3 |
| S = 1.02 | Δρmin = −0.28 e Å−3 |
| 5293 reflections | Absolute structure: ? |
| 289 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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. |
| x | y | z | Uiso*/Ueq | ||
| Ni1 | 0.25048 (3) | 1.00150 (2) | −0.002820 (16) | 0.03427 (8) | |
| O1 | 0.22183 (18) | 1.16579 (11) | 0.01506 (9) | 0.0429 (3) | |
| O2 | 0.20302 (18) | 1.04717 (11) | −0.13928 (9) | 0.0417 (3) | |
| N1 | 0.30698 (19) | 0.96456 (13) | 0.13543 (11) | 0.0351 (3) | |
| N2 | 0.26661 (19) | 0.83899 (13) | −0.02841 (10) | 0.0337 (3) | |
| C1 | 0.1646 (2) | 1.22188 (16) | 0.09929 (14) | 0.0376 (4) | |
| C2 | 0.1041 (3) | 1.35083 (18) | 0.09098 (15) | 0.0473 (5) | |
| H2A | 0.1129 | 1.3909 | 0.0282 | 0.057* | |
| C3 | 0.0340 (3) | 1.41573 (19) | 0.17329 (17) | 0.0528 (5) | |
| H3A | −0.0049 | 1.4997 | 0.1655 | 0.063* | |
| C4 | 0.0180 (3) | 1.35973 (19) | 0.27082 (15) | 0.0468 (5) | |
| C5 | −0.0599 (3) | 1.4277 (2) | 0.35586 (19) | 0.0611 (6) | |
| H5A | −0.1016 | 1.5114 | 0.3481 | 0.073* | |
| C6 | −0.0747 (3) | 1.3721 (3) | 0.44875 (19) | 0.0672 (7) | |
| H6A | −0.1248 | 1.4179 | 0.5043 | 0.081* | |
| C7 | −0.0150 (3) | 1.2469 (3) | 0.46062 (16) | 0.0607 (6) | |
| H7A | −0.0265 | 1.2091 | 0.5241 | 0.073* | |
| C8 | 0.0610 (3) | 1.1785 (2) | 0.37951 (15) | 0.0503 (5) | |
| H8A | 0.0988 | 1.0947 | 0.3887 | 0.060* | |
| C9 | 0.0826 (2) | 1.23247 (18) | 0.28295 (14) | 0.0410 (4) | |
| C10 | 0.1613 (2) | 1.16358 (17) | 0.19568 (13) | 0.0365 (4) | |
| C11 | 0.2568 (2) | 1.03958 (17) | 0.20838 (13) | 0.0373 (4) | |
| H11A | 0.2857 | 1.0099 | 0.2752 | 0.045* | |
| C12 | 0.4315 (2) | 0.84660 (16) | 0.15985 (14) | 0.0395 (4) | |
| H12A | 0.4724 | 0.8452 | 0.2305 | 0.047* | |
| H12B | 0.5387 | 0.8369 | 0.1159 | 0.047* | |
| C13 | 0.3433 (3) | 0.73967 (16) | 0.14614 (14) | 0.0402 (4) | |
| C14 | 0.2095 (3) | 0.76569 (17) | 0.05547 (13) | 0.0405 (4) | |
| H14A | 0.1980 | 0.6893 | 0.0288 | 0.049* | |
| H14B | 0.0896 | 0.8079 | 0.0798 | 0.049* | |
| C15 | 0.3060 (2) | 0.79094 (16) | −0.11691 (13) | 0.0357 (4) | |
| H15A | 0.3179 | 0.7077 | −0.1198 | 0.043* | |
| C16 | 0.3326 (2) | 0.85414 (16) | −0.21032 (13) | 0.0334 (4) | |
| C17 | 0.4069 (2) | 0.78886 (16) | −0.30034 (13) | 0.0349 (4) | |
| C18 | 0.4910 (3) | 0.66487 (18) | −0.29783 (15) | 0.0467 (5) | |
| H18A | 0.5003 | 0.6210 | −0.2355 | 0.056* | |
| C19 | 0.5602 (3) | 0.6063 (2) | −0.38503 (17) | 0.0543 (5) | |
| H19A | 0.6147 | 0.5236 | −0.3810 | 0.065* | |
| C20 | 0.5499 (3) | 0.6689 (2) | −0.47890 (16) | 0.0553 (6) | |
| H20A | 0.5966 | 0.6284 | −0.5377 | 0.066* | |
| C21 | 0.4713 (3) | 0.7895 (2) | −0.48451 (15) | 0.0490 (5) | |
| H21A | 0.4645 | 0.8314 | −0.5477 | 0.059* | |
| C22 | 0.3996 (2) | 0.85265 (17) | −0.39621 (13) | 0.0385 (4) | |
| C23 | 0.3185 (3) | 0.97905 (18) | −0.40085 (14) | 0.0437 (4) | |
| H23A | 0.3093 | 1.0209 | −0.4641 | 0.052* | |
| C24 | 0.2541 (3) | 1.04042 (17) | −0.31591 (13) | 0.0418 (4) | |
| H24A | 0.2027 | 1.1234 | −0.3219 | 0.050* | |
| C25 | 0.2638 (2) | 0.98001 (16) | −0.21745 (13) | 0.0345 (4) | |
| C26 | 0.2337 (3) | 0.7194 (2) | 0.24235 (16) | 0.0643 (6) | |
| H26A | 0.1385 | 0.7910 | 0.2535 | 0.096* | |
| H26B | 0.3141 | 0.7027 | 0.3008 | 0.096* | |
| H26C | 0.1798 | 0.6519 | 0.2330 | 0.096* | |
| C27 | 0.4978 (3) | 0.6277 (2) | 0.1266 (2) | 0.0680 (7) | |
| H27A | 0.5647 | 0.6425 | 0.0662 | 0.102* | |
| H27B | 0.4465 | 0.5592 | 0.1168 | 0.102* | |
| H27C | 0.5793 | 0.6113 | 0.1846 | 0.102* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Ni1 | 0.04204 (14) | 0.03339 (13) | 0.02735 (13) | −0.00840 (9) | 0.00091 (9) | −0.00494 (9) |
| O1 | 0.0599 (8) | 0.0363 (7) | 0.0329 (7) | −0.0114 (6) | 0.0073 (6) | −0.0074 (5) |
| O2 | 0.0568 (8) | 0.0342 (7) | 0.0299 (6) | −0.0021 (6) | 0.0002 (6) | −0.0039 (5) |
| N1 | 0.0380 (8) | 0.0368 (8) | 0.0313 (8) | −0.0099 (7) | 0.0004 (6) | −0.0037 (6) |
| N2 | 0.0391 (8) | 0.0354 (8) | 0.0276 (7) | −0.0105 (6) | −0.0005 (6) | −0.0014 (6) |
| C1 | 0.0387 (9) | 0.0386 (10) | 0.0374 (10) | −0.0116 (8) | 0.0002 (7) | −0.0094 (8) |
| C2 | 0.0562 (12) | 0.0402 (11) | 0.0469 (11) | −0.0134 (9) | 0.0001 (9) | −0.0071 (9) |
| C3 | 0.0546 (12) | 0.0410 (11) | 0.0629 (14) | −0.0090 (10) | −0.0027 (10) | −0.0165 (10) |
| C4 | 0.0404 (10) | 0.0527 (12) | 0.0483 (12) | −0.0096 (9) | 0.0003 (8) | −0.0236 (10) |
| C5 | 0.0497 (12) | 0.0629 (15) | 0.0685 (16) | −0.0042 (11) | 0.0026 (11) | −0.0362 (13) |
| C6 | 0.0504 (13) | 0.096 (2) | 0.0538 (15) | −0.0083 (13) | 0.0074 (10) | −0.0419 (14) |
| C7 | 0.0506 (12) | 0.091 (2) | 0.0405 (12) | −0.0154 (13) | 0.0052 (9) | −0.0209 (12) |
| C8 | 0.0456 (11) | 0.0685 (14) | 0.0376 (11) | −0.0138 (10) | 0.0017 (8) | −0.0140 (10) |
| C9 | 0.0319 (9) | 0.0539 (12) | 0.0391 (10) | −0.0115 (8) | −0.0010 (7) | −0.0177 (9) |
| C10 | 0.0355 (9) | 0.0435 (10) | 0.0329 (9) | −0.0125 (8) | 0.0004 (7) | −0.0113 (8) |
| C11 | 0.0387 (9) | 0.0454 (11) | 0.0294 (9) | −0.0125 (8) | −0.0002 (7) | −0.0048 (8) |
| C12 | 0.0404 (10) | 0.0402 (10) | 0.0363 (10) | −0.0063 (8) | −0.0045 (8) | −0.0014 (8) |
| C13 | 0.0485 (11) | 0.0368 (10) | 0.0352 (10) | −0.0102 (9) | −0.0012 (8) | 0.0023 (8) |
| C14 | 0.0496 (11) | 0.0424 (10) | 0.0336 (10) | −0.0193 (9) | 0.0020 (8) | −0.0008 (8) |
| C15 | 0.0395 (9) | 0.0326 (9) | 0.0360 (10) | −0.0098 (8) | −0.0021 (7) | −0.0038 (8) |
| C16 | 0.0348 (9) | 0.0371 (10) | 0.0294 (9) | −0.0100 (8) | −0.0010 (7) | −0.0043 (7) |
| C17 | 0.0334 (9) | 0.0414 (10) | 0.0317 (9) | −0.0118 (8) | −0.0014 (7) | −0.0060 (8) |
| C18 | 0.0531 (12) | 0.0439 (11) | 0.0412 (11) | −0.0070 (9) | 0.0023 (9) | −0.0063 (9) |
| C19 | 0.0575 (13) | 0.0458 (12) | 0.0558 (14) | −0.0030 (10) | 0.0071 (10) | −0.0158 (10) |
| C20 | 0.0583 (13) | 0.0654 (15) | 0.0435 (12) | −0.0148 (11) | 0.0142 (10) | −0.0235 (11) |
| C21 | 0.0558 (12) | 0.0631 (14) | 0.0321 (10) | −0.0212 (11) | 0.0073 (9) | −0.0093 (9) |
| C22 | 0.0397 (10) | 0.0471 (11) | 0.0313 (9) | −0.0148 (8) | 0.0004 (7) | −0.0075 (8) |
| C23 | 0.0534 (11) | 0.0492 (12) | 0.0297 (9) | −0.0150 (9) | −0.0035 (8) | 0.0023 (8) |
| C24 | 0.0522 (11) | 0.0379 (10) | 0.0343 (10) | −0.0087 (9) | −0.0045 (8) | −0.0003 (8) |
| C25 | 0.0372 (9) | 0.0373 (10) | 0.0297 (9) | −0.0093 (8) | −0.0022 (7) | −0.0054 (7) |
| C26 | 0.0814 (16) | 0.0800 (17) | 0.0403 (12) | −0.0387 (14) | 0.0001 (11) | 0.0106 (11) |
| C27 | 0.0766 (16) | 0.0431 (13) | 0.0787 (17) | −0.0029 (12) | −0.0123 (13) | −0.0017 (11) |
| Ni1—O2 | 1.8453 (12) | C12—H12B | 0.9700 |
| Ni1—O1 | 1.8501 (12) | C13—C27 | 1.530 (3) |
| Ni1—N1 | 1.8617 (14) | C13—C14 | 1.530 (2) |
| Ni1—N2 | 1.8632 (14) | C13—C26 | 1.532 (3) |
| O1—C1 | 1.306 (2) | C14—H14A | 0.9700 |
| O2—C25 | 1.308 (2) | C14—H14B | 0.9700 |
| N1—C11 | 1.293 (2) | C15—C16 | 1.426 (2) |
| N1—C12 | 1.464 (2) | C15—H15A | 0.9300 |
| N2—C15 | 1.295 (2) | C16—C25 | 1.399 (2) |
| N2—C14 | 1.470 (2) | C16—C17 | 1.446 (2) |
| C1—C10 | 1.399 (3) | C17—C18 | 1.398 (3) |
| C1—C2 | 1.426 (3) | C17—C22 | 1.414 (2) |
| C2—C3 | 1.354 (3) | C18—C19 | 1.372 (3) |
| C2—H2A | 0.9300 | C18—H18A | 0.9300 |
| C3—C4 | 1.416 (3) | C19—C20 | 1.384 (3) |
| C3—H3A | 0.9300 | C19—H19A | 0.9300 |
| C4—C9 | 1.414 (3) | C20—C21 | 1.356 (3) |
| C4—C5 | 1.414 (3) | C20—H20A | 0.9300 |
| C5—C6 | 1.359 (3) | C21—C22 | 1.411 (2) |
| C5—H5A | 0.9300 | C21—H21A | 0.9300 |
| C6—C7 | 1.388 (3) | C22—C23 | 1.419 (3) |
| C6—H6A | 0.9300 | C23—C24 | 1.353 (2) |
| C7—C8 | 1.372 (3) | C23—H23A | 0.9300 |
| C7—H7A | 0.9300 | C24—C25 | 1.425 (2) |
| C8—C9 | 1.403 (3) | C24—H24A | 0.9300 |
| C8—H8A | 0.9300 | C26—H26A | 0.9600 |
| C9—C10 | 1.444 (2) | C26—H26B | 0.9600 |
| C10—C11 | 1.424 (3) | C26—H26C | 0.9600 |
| C11—H11A | 0.9300 | C27—H27A | 0.9600 |
| C12—C13 | 1.532 (2) | C27—H27B | 0.9600 |
| C12—H12A | 0.9700 | C27—H27C | 0.9600 |
| O2—Ni1—O1 | 84.48 (5) | C14—C13—C12 | 110.48 (14) |
| O2—Ni1—N1 | 175.84 (6) | C27—C13—C26 | 110.90 (18) |
| O1—Ni1—N1 | 92.08 (6) | C14—C13—C26 | 107.42 (16) |
| O2—Ni1—N2 | 92.02 (6) | C12—C13—C26 | 110.25 (16) |
| O1—Ni1—N2 | 175.83 (6) | N2—C14—C13 | 113.35 (14) |
| N1—Ni1—N2 | 91.51 (6) | N2—C14—H14A | 108.9 |
| C1—O1—Ni1 | 125.17 (12) | C13—C14—H14A | 108.9 |
| C25—O2—Ni1 | 125.40 (11) | N2—C14—H14B | 108.9 |
| C11—N1—C12 | 118.80 (15) | C13—C14—H14B | 108.9 |
| C11—N1—Ni1 | 124.30 (13) | H14A—C14—H14B | 107.7 |
| C12—N1—Ni1 | 116.62 (11) | N2—C15—C16 | 125.85 (16) |
| C15—N2—C14 | 118.61 (15) | N2—C15—H15A | 117.1 |
| C15—N2—Ni1 | 124.48 (12) | C16—C15—H15A | 117.1 |
| C14—N2—Ni1 | 116.51 (11) | C25—C16—C15 | 118.56 (15) |
| O1—C1—C10 | 124.15 (17) | C25—C16—C17 | 120.04 (16) |
| O1—C1—C2 | 116.95 (17) | C15—C16—C17 | 120.90 (16) |
| C10—C1—C2 | 118.90 (17) | C18—C17—C22 | 117.34 (16) |
| C3—C2—C1 | 120.88 (19) | C18—C17—C16 | 123.42 (16) |
| C3—C2—H2A | 119.6 | C22—C17—C16 | 119.22 (16) |
| C1—C2—H2A | 119.6 | C19—C18—C17 | 121.63 (19) |
| C2—C3—C4 | 122.0 (2) | C19—C18—H18A | 119.2 |
| C2—C3—H3A | 119.0 | C17—C18—H18A | 119.2 |
| C4—C3—H3A | 119.0 | C18—C19—C20 | 120.7 (2) |
| C9—C4—C5 | 119.5 (2) | C18—C19—H19A | 119.6 |
| C9—C4—C3 | 118.73 (17) | C20—C19—H19A | 119.6 |
| C5—C4—C3 | 121.8 (2) | C21—C20—C19 | 119.53 (19) |
| C6—C5—C4 | 120.9 (2) | C21—C20—H20A | 120.2 |
| C6—C5—H5A | 119.6 | C19—C20—H20A | 120.2 |
| C4—C5—H5A | 119.6 | C20—C21—C22 | 121.19 (19) |
| C5—C6—C7 | 119.9 (2) | C20—C21—H21A | 119.4 |
| C5—C6—H6A | 120.0 | C22—C21—H21A | 119.4 |
| C7—C6—H6A | 120.0 | C21—C22—C17 | 119.57 (18) |
| C8—C7—C6 | 120.6 (2) | C21—C22—C23 | 121.76 (18) |
| C8—C7—H7A | 119.7 | C17—C22—C23 | 118.68 (16) |
| C6—C7—H7A | 119.7 | C24—C23—C22 | 121.89 (17) |
| C7—C8—C9 | 121.3 (2) | C24—C23—H23A | 119.1 |
| C7—C8—H8A | 119.3 | C22—C23—H23A | 119.1 |
| C9—C8—H8A | 119.3 | C23—C24—C25 | 121.08 (18) |
| C8—C9—C4 | 117.77 (18) | C23—C24—H24A | 119.5 |
| C8—C9—C10 | 122.98 (19) | C25—C24—H24A | 119.5 |
| C4—C9—C10 | 119.22 (18) | O2—C25—C16 | 124.25 (16) |
| C1—C10—C11 | 118.64 (16) | O2—C25—C24 | 116.85 (16) |
| C1—C10—C9 | 120.05 (18) | C16—C25—C24 | 118.88 (16) |
| C11—C10—C9 | 120.84 (17) | C13—C26—H26A | 109.5 |
| N1—C11—C10 | 125.94 (17) | C13—C26—H26B | 109.5 |
| N1—C11—H11A | 117.0 | H26A—C26—H26B | 109.5 |
| C10—C11—H11A | 117.0 | C13—C26—H26C | 109.5 |
| N1—C12—C13 | 113.23 (14) | H26A—C26—H26C | 109.5 |
| N1—C12—H12A | 108.9 | H26B—C26—H26C | 109.5 |
| C13—C12—H12A | 108.9 | C13—C27—H27A | 109.5 |
| N1—C12—H12B | 108.9 | C13—C27—H27B | 109.5 |
| C13—C12—H12B | 108.9 | H27A—C27—H27B | 109.5 |
| H12A—C12—H12B | 107.7 | C13—C27—H27C | 109.5 |
| C27—C13—C14 | 110.24 (16) | H27A—C27—H27C | 109.5 |
| C27—C13—C12 | 107.57 (17) | H27B—C27—H27C | 109.5 |
| O2—Ni1—O1—C1 | 151.46 (15) | C9—C10—C11—N1 | 168.37 (17) |
| N1—Ni1—O1—C1 | −30.88 (15) | C11—N1—C12—C13 | 114.41 (18) |
| O1—Ni1—O2—C25 | 151.58 (14) | Ni1—N1—C12—C13 | −71.51 (17) |
| N2—Ni1—O2—C25 | −30.68 (14) | N1—C12—C13—C27 | 155.32 (16) |
| O1—Ni1—N1—C11 | 24.19 (15) | N1—C12—C13—C14 | 35.0 (2) |
| N2—Ni1—N1—C11 | −153.69 (15) | N1—C12—C13—C26 | −83.63 (19) |
| O1—Ni1—N1—C12 | −149.53 (12) | C15—N2—C14—C13 | 115.85 (17) |
| N2—Ni1—N1—C12 | 32.58 (12) | Ni1—N2—C14—C13 | −71.04 (18) |
| O2—Ni1—N2—C15 | 23.74 (14) | C27—C13—C14—N2 | −85.4 (2) |
| N1—Ni1—N2—C15 | −154.06 (14) | C12—C13—C14—N2 | 33.4 (2) |
| O2—Ni1—N2—C14 | −148.93 (12) | C26—C13—C14—N2 | 153.68 (16) |
| N1—Ni1—N2—C14 | 33.28 (12) | C14—N2—C15—C16 | 168.55 (16) |
| Ni1—O1—C1—C10 | 17.2 (2) | Ni1—N2—C15—C16 | −4.0 (2) |
| Ni1—O1—C1—C2 | −163.52 (13) | N2—C15—C16—C25 | −18.9 (3) |
| O1—C1—C2—C3 | 176.67 (17) | N2—C15—C16—C17 | 169.17 (16) |
| C10—C1—C2—C3 | −4.0 (3) | C25—C16—C17—C18 | 174.81 (17) |
| C1—C2—C3—C4 | 0.3 (3) | C15—C16—C17—C18 | −13.4 (3) |
| C2—C3—C4—C9 | 2.0 (3) | C25—C16—C17—C22 | −3.5 (2) |
| C2—C3—C4—C5 | −178.28 (19) | C15—C16—C17—C22 | 168.25 (16) |
| C9—C4—C5—C6 | −0.5 (3) | C22—C17—C18—C19 | −1.5 (3) |
| C3—C4—C5—C6 | 179.7 (2) | C16—C17—C18—C19 | −179.85 (18) |
| C4—C5—C6—C7 | −0.8 (3) | C17—C18—C19—C20 | 0.4 (3) |
| C5—C6—C7—C8 | 0.7 (3) | C18—C19—C20—C21 | 0.3 (3) |
| C6—C7—C8—C9 | 0.8 (3) | C19—C20—C21—C22 | 0.0 (3) |
| C7—C8—C9—C4 | −2.0 (3) | C20—C21—C22—C17 | −1.1 (3) |
| C7—C8—C9—C10 | −179.83 (18) | C20—C21—C22—C23 | 179.44 (19) |
| C5—C4—C9—C8 | 1.9 (3) | C18—C17—C22—C21 | 1.8 (2) |
| C3—C4—C9—C8 | −178.36 (18) | C16—C17—C22—C21 | −179.80 (16) |
| C5—C4—C9—C10 | 179.77 (17) | C18—C17—C22—C23 | −178.73 (17) |
| C3—C4—C9—C10 | −0.5 (3) | C16—C17—C22—C23 | −0.3 (2) |
| O1—C1—C10—C11 | 12.5 (3) | C21—C22—C23—C24 | −178.18 (18) |
| C2—C1—C10—C11 | −166.77 (16) | C17—C22—C23—C24 | 2.3 (3) |
| O1—C1—C10—C9 | −175.30 (16) | C22—C23—C24—C25 | −0.5 (3) |
| C2—C1—C10—C9 | 5.5 (2) | Ni1—O2—C25—C16 | 17.6 (2) |
| C8—C9—C10—C1 | 174.51 (17) | Ni1—O2—C25—C24 | −163.95 (12) |
| C4—C9—C10—C1 | −3.3 (2) | C15—C16—C25—O2 | 11.7 (3) |
| C8—C9—C10—C11 | −13.4 (3) | C17—C16—C25—O2 | −176.29 (15) |
| C4—C9—C10—C11 | 168.79 (16) | C15—C16—C25—C24 | −166.67 (16) |
| C12—N1—C11—C10 | 169.46 (16) | C17—C16—C25—C24 | 5.3 (2) |
| Ni1—N1—C11—C10 | −4.1 (2) | C23—C24—C25—O2 | 178.13 (17) |
| C1—C10—C11—N1 | −19.5 (3) | C23—C24—C25—C16 | −3.3 (3) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C12—H12B···O1i | 0.97 | 2.46 | 3.422 (2) | 171 |
| C14—H14B···O2ii | 0.97 | 2.54 | 3.502 (2) | 170 |
| Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x, −y+2, −z. |
| Ni1—O2 | 1.8453 (12) | Ni1—N1 | 1.8617 (14) |
| Ni1—O1 | 1.8501 (12) | Ni1—N2 | 1.8632 (14) |
| O2—Ni1—O1 | 84.48 (5) | O2—Ni1—N2 | 92.02 (6) |
| O1—Ni1—N1 | 92.08 (6) | N1—Ni1—N2 | 91.51 (6) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C12—H12B···O1i | 0.97 | 2.46 | 3.422 (2) | 171 |
| C14—H14B···O2ii | 0.97 | 2.54 | 3.502 (2) | 170 |
| Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x, −y+2, −z. |
HK and RK thank PNU for financial support and RK also thanks Islamic Azad University. IUK thanks GC University of Lahore, Pakistan, for the research facilities.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
Blower, P. J. (1998). Transition Met. Chem. 23, 109–112.
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Elmali, A., Elerman, Y. & Svoboda, I. (2000). Acta Cryst. C56, 423–424.
Granovski, A. D., Nivorozhkin, A. L. & Minkin, V. I. (1993). Coord. Chem. Rev. 126, 1–69.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Spek, A. L. (2009). Acta Cryst. D65, 148–155.
Schiff base complexes are one of the most important stereochemical models in transition metal coordination chemistry, with the ease of preparation and structural variations (Granovski et al., 1993). Metal derivatives of the Schiff bases have been studied extensively, and Ni(II) and Cu(II) complexes play a major role in both synthetic and structural research (Elmali et al., 2000; Blower et al., 1998). The asymmetric unit of the title compound, Fig. 1, comprises one unit of the Schiff base complex. The bond lengths (Allen et al., 1987) and angles are within the normal ranges. The geometry around the Ni(II) atom is a slightly distorted square-planar which is coordinated by the N2O2 donor atoms of the desired potentially tetradenate Schiff base ligand (Table 1). Pairs of weak intermolecular C—H···O hydrogen bonds (Table 2) link neighboring molecules into a chain along the a-axis. The dihedral angle between the mean planes of the two aromatic rings is 6.16 (6)°. The crystal structure is further stabilized by the intermolecular π–π interactions [Cg1···Cg2i = 3.7252 (13) and Cg1···Cg2ii = 3.8323 (13) Å; Cg1 and Cg2 are the centroids of the C4/C5/C6/C7/C8/C9 and C17/C18/C19/C20/C21/C22 benzene rings].