Acta Cryst. (2008). E64, m1088 [ doi:10.1107/S1600536808023489 ]
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3O2,N,O]tripyridinenickel(II) pyridine solvateIn the title compound, [Ni(C16H8N2O4)(C5H5N)3]·C5H5N, the NiII atom is six-coordinated by two O atoms and one N atom from the Schiff base ligand and by three N atoms from three pyridine molecules, forming a distorted octahedral geometry. The Ni-O(phenolate) bond [1.9750 (16) Å] is shorter than the Ni-O(carbonyl) bond [2.0840 (16) Å] and the Ni-N bonds (mean 2.120 Å).
To a cold solution of 2-hydroxybenzhydrazide (3.04 g, 20 mmol) in absolute ethyl alcohol (25 ml) was added dropwise a solution of triketohydrindene hydrate (3.2 g, 20 mmol) in absolute ethyl alcohol (25 ml). Stirring was continued at room temperature for 10 min, then refluxing at 351 K for 2 h. After filtering, the filtrate was the schiff base (H2L) as yellow solid. To a solution of ligand (0.47 g, 1.6 mmol) in ethyl acetate (15 ml) was added slowly a solution of Ni(ac)2.2H2O (0.34 g, 1.6 mmol) in ethyl acetate (10 ml). The mixture was stirred for 2 h until a brown precipitate appeared. The precipitate was collected and washed three times with ethyl acetate. Further drying in vacuum afforded a brown powder. Brown single crystals of NiL.4(C5H5N) were grown from methanol and pyridine mixed solution (2:1 v/v) with slow evaporation at room temperature.
All H were placed in geometrically idealized positions (C—H = 0.93 Å) and were treated as riding atoms, with Uiso(H) = 1.2Ueq(C).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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: publCIF (Westrip, 2008).
![[Figure 1]](./is2292fig1thm.gif)
| Fig. 1. The molecular structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity. |
![[Figure 2]](./is2292fig2thm.gif)
| Fig. 2. A partial packing diagram of the title compound. |
| [Ni(C16H8N2O4)(C5H5N)3]·C5H5N | F000 = 2768 |
| Mr = 667.35 | Dx = 1.358 Mg m−3 |
| Orthorhombic, Pbca | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -P 2ac 2ab | Cell parameters from 4952 reflections |
| a = 17.1945 (13) Å | θ = 2.2–21.5º |
| b = 17.6887 (13) Å | µ = 0.64 mm−1 |
| c = 21.4633 (16) Å | T = 273 (2) K |
| V = 6528.0 (8) Å3 | Block, brown |
| Z = 8 | 0.19 × 0.18 × 0.15 mm |
| Bruker SMART 1000 CCD area-detector diffractometer | 7115 independent reflections |
| Radiation source: fine-focus sealed tube | 4248 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.058 |
| T = 273(2) K | θmax = 27.0º |
| φ and ω scans | θmin = 1.9º |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −20→21 |
| Tmin = 0.885, Tmax = 0.908 | k = −18→22 |
| 36292 measured reflections | l = −24→27 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
| wR(F2) = 0.093 | w = 1/[σ2(Fo2) + (0.031P)2 + 1.8991P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.00 | (Δ/σ)max = 0.001 |
| 7115 reflections | Δρmax = 0.25 e Å−3 |
| 424 parameters | Δρmin = −0.26 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| [Ni(C16H8N2O4)(C5H5N)3]·C5H5N | V = 6528.0 (8) Å3 |
| Mr = 667.35 | Z = 8 |
| Orthorhombic, Pbca | Mo Kα |
| a = 17.1945 (13) Å | µ = 0.64 mm−1 |
| b = 17.6887 (13) Å | T = 273 (2) K |
| c = 21.4633 (16) Å | 0.19 × 0.18 × 0.15 mm |
| Bruker SMART 1000 CCD area-detector diffractometer | 7115 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4248 reflections with I > 2σ(I) |
| Tmin = 0.885, Tmax = 0.908 | Rint = 0.058 |
| 36292 measured reflections |
| R[F2 > 2σ(F2)] = 0.038 | 424 parameters |
| wR(F2) = 0.093 | H-atom parameters constrained |
| S = 1.00 | Δρmax = 0.25 e Å−3 |
| 7115 reflections | Δρmin = −0.26 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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. |
| x | y | z | Uiso*/Ueq | ||
| Ni1 | 0.836338 (16) | 0.083641 (16) | 0.657583 (13) | 0.04341 (10) | |
| C1 | 0.76080 (12) | 0.18336 (13) | 0.48329 (11) | 0.0453 (6) | |
| C2 | 0.75643 (14) | 0.26298 (14) | 0.47940 (12) | 0.0565 (7) | |
| H2 | 0.7638 | 0.2930 | 0.5145 | 0.068* | |
| C3 | 0.74079 (15) | 0.29530 (16) | 0.42153 (13) | 0.0643 (7) | |
| H3 | 0.7383 | 0.3476 | 0.4174 | 0.077* | |
| C4 | 0.72894 (15) | 0.24950 (17) | 0.37029 (13) | 0.0668 (8) | |
| H4 | 0.7185 | 0.2719 | 0.3320 | 0.080* | |
| C5 | 0.73212 (14) | 0.16902 (15) | 0.37408 (12) | 0.0595 (7) | |
| H5 | 0.7235 | 0.1393 | 0.3390 | 0.071* | |
| C6 | 0.74836 (13) | 0.13645 (14) | 0.43112 (11) | 0.0463 (6) | |
| C7 | 0.75640 (13) | 0.05326 (14) | 0.44978 (11) | 0.0476 (6) | |
| C8 | 0.77700 (13) | 0.05377 (13) | 0.51617 (10) | 0.0431 (5) | |
| C9 | 0.77869 (12) | 0.13320 (13) | 0.53733 (11) | 0.0433 (6) | |
| C10 | 0.80145 (16) | −0.08939 (15) | 0.63042 (12) | 0.0568 (7) | |
| C11 | 0.84936 (14) | −0.11063 (14) | 0.68389 (11) | 0.0489 (6) | |
| C12 | 0.85576 (15) | −0.19104 (15) | 0.69505 (13) | 0.0615 (7) | |
| H12 | 0.8306 | −0.2240 | 0.6680 | 0.074* | |
| C13 | 0.89690 (16) | −0.22044 (16) | 0.74336 (14) | 0.0693 (8) | |
| H13 | 0.9009 | −0.2724 | 0.7493 | 0.083* | |
| C14 | 0.93282 (16) | −0.16944 (17) | 0.78369 (14) | 0.0692 (8) | |
| H14 | 0.9608 | −0.1880 | 0.8175 | 0.083* | |
| C15 | 0.92794 (14) | −0.09100 (15) | 0.77480 (12) | 0.0590 (7) | |
| H15 | 0.9527 | −0.0593 | 0.8031 | 0.071* | |
| C16 | 0.88692 (13) | −0.05805 (14) | 0.72444 (11) | 0.0470 (6) | |
| C17 | 0.72290 (15) | 0.05699 (15) | 0.76300 (11) | 0.0568 (7) | |
| H17 | 0.7682 | 0.0546 | 0.7866 | 0.068* | |
| C18 | 0.65464 (16) | 0.04440 (16) | 0.79189 (12) | 0.0644 (7) | |
| H18 | 0.6528 | 0.0336 | 0.8343 | 0.077* | |
| C19 | 0.58917 (15) | 0.04784 (15) | 0.75774 (12) | 0.0616 (7) | |
| H19 | 0.5409 | 0.0396 | 0.7761 | 0.074* | |
| C20 | 0.59477 (14) | 0.06369 (16) | 0.69538 (13) | 0.0630 (7) | |
| H20 | 0.5502 | 0.0660 | 0.6709 | 0.076* | |
| C21 | 0.66456 (14) | 0.07584 (15) | 0.67011 (11) | 0.0579 (7) | |
| H21 | 0.6675 | 0.0870 | 0.6278 | 0.069* | |
| C22 | 0.84087 (14) | 0.25500 (15) | 0.69829 (12) | 0.0577 (7) | |
| H22 | 0.8132 | 0.2617 | 0.6615 | 0.069* | |
| C23 | 0.85674 (17) | 0.31949 (16) | 0.73437 (14) | 0.0702 (8) | |
| H23 | 0.8403 | 0.3672 | 0.7217 | 0.084* | |
| C24 | 0.89680 (17) | 0.31003 (18) | 0.78832 (15) | 0.0756 (9) | |
| H24 | 0.9084 | 0.3511 | 0.8137 | 0.091* | |
| C25 | 0.92010 (16) | 0.23715 (18) | 0.80478 (14) | 0.0720 (8) | |
| H25 | 0.9478 | 0.2295 | 0.8414 | 0.086* | |
| C26 | 0.90217 (15) | 0.17552 (16) | 0.76671 (12) | 0.0619 (7) | |
| H26 | 0.9180 | 0.1275 | 0.7789 | 0.074* | |
| C27 | 0.96595 (17) | 0.15987 (18) | 0.58237 (15) | 0.0824 (10) | |
| H27 | 0.9369 | 0.2034 | 0.5893 | 0.099* | |
| C28 | 1.0323 (2) | 0.1649 (2) | 0.54845 (18) | 0.1044 (12) | |
| H28 | 1.0491 | 0.2109 | 0.5324 | 0.125* | |
| C29 | 1.07387 (18) | 0.0991 (2) | 0.53864 (16) | 0.0895 (11) | |
| H29 | 1.1197 | 0.1008 | 0.5157 | 0.107* | |
| C30 | 1.04850 (16) | 0.0314 (2) | 0.56227 (13) | 0.0723 (9) | |
| H30 | 1.0762 | −0.0130 | 0.5551 | 0.087* | |
| C31 | 0.98246 (14) | 0.03074 (16) | 0.59608 (11) | 0.0572 (7) | |
| H31 | 0.9652 | −0.0148 | 0.6128 | 0.069* | |
| C32 | 0.4254 (3) | 0.1039 (2) | 0.5441 (2) | 0.1206 (14) | |
| H32 | 0.3875 | 0.0997 | 0.5749 | 0.145* | |
| C33 | 0.4032 (2) | 0.0948 (2) | 0.4840 (2) | 0.1056 (12) | |
| H33 | 0.3512 | 0.0867 | 0.4739 | 0.127* | |
| C34 | 0.4572 (3) | 0.0977 (2) | 0.43937 (19) | 0.1094 (13) | |
| H34 | 0.4443 | 0.0909 | 0.3977 | 0.131* | |
| C35 | 0.5290 (3) | 0.1106 (2) | 0.4563 (2) | 0.1157 (14) | |
| H35 | 0.5682 | 0.1125 | 0.4265 | 0.139* | |
| C36 | 0.5462 (2) | 0.1208 (3) | 0.5161 (2) | 0.1186 (14) | |
| H36 | 0.5977 | 0.1308 | 0.5263 | 0.142* | |
| N1 | 0.78470 (10) | −0.01309 (11) | 0.54711 (9) | 0.0448 (5) | |
| N2 | 0.80692 (10) | −0.01229 (10) | 0.60518 (9) | 0.0441 (5) | |
| N3 | 0.72906 (11) | 0.07276 (11) | 0.70230 (9) | 0.0464 (5) | |
| N4 | 0.86311 (11) | 0.18326 (11) | 0.71342 (9) | 0.0496 (5) | |
| N5 | 0.94071 (11) | 0.09374 (12) | 0.60636 (9) | 0.0538 (5) | |
| N6 | 0.4958 (2) | 0.1180 (2) | 0.56149 (16) | 0.1264 (12) | |
| O1 | 0.79103 (9) | 0.15745 (8) | 0.59117 (7) | 0.0493 (4) | |
| O2 | 0.74742 (11) | −0.00276 (10) | 0.41554 (8) | 0.0645 (5) | |
| O3 | 0.75743 (14) | −0.13547 (12) | 0.60754 (9) | 0.0958 (8) | |
| O4 | 0.88726 (9) | 0.01748 (9) | 0.71947 (7) | 0.0523 (4) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Ni1 | 0.03906 (16) | 0.04585 (18) | 0.04532 (18) | −0.00026 (14) | 0.00063 (14) | −0.00265 (15) |
| C1 | 0.0367 (13) | 0.0499 (16) | 0.0493 (14) | 0.0019 (11) | 0.0044 (10) | 0.0021 (12) |
| C2 | 0.0575 (16) | 0.0531 (17) | 0.0589 (17) | 0.0006 (13) | 0.0035 (13) | −0.0007 (14) |
| C3 | 0.0672 (19) | 0.0513 (17) | 0.074 (2) | 0.0031 (14) | −0.0003 (15) | 0.0094 (16) |
| C4 | 0.0692 (18) | 0.066 (2) | 0.0651 (18) | 0.0006 (15) | −0.0071 (14) | 0.0201 (16) |
| C5 | 0.0590 (17) | 0.069 (2) | 0.0506 (16) | −0.0045 (14) | −0.0020 (12) | 0.0041 (14) |
| C6 | 0.0387 (13) | 0.0524 (15) | 0.0479 (15) | 0.0011 (11) | 0.0044 (11) | 0.0037 (12) |
| C7 | 0.0434 (14) | 0.0521 (15) | 0.0472 (14) | 0.0000 (12) | 0.0034 (11) | −0.0017 (13) |
| C8 | 0.0399 (13) | 0.0467 (14) | 0.0425 (13) | 0.0003 (11) | 0.0029 (10) | 0.0018 (12) |
| C9 | 0.0339 (12) | 0.0486 (15) | 0.0473 (14) | 0.0019 (10) | 0.0059 (10) | 0.0001 (12) |
| C10 | 0.0708 (17) | 0.0490 (16) | 0.0506 (15) | −0.0109 (14) | −0.0028 (13) | 0.0008 (13) |
| C11 | 0.0497 (15) | 0.0473 (15) | 0.0496 (14) | 0.0008 (12) | 0.0025 (12) | 0.0044 (12) |
| C12 | 0.0693 (19) | 0.0509 (17) | 0.0644 (18) | −0.0017 (14) | 0.0060 (14) | 0.0030 (14) |
| C13 | 0.071 (2) | 0.0537 (18) | 0.084 (2) | 0.0101 (15) | 0.0059 (17) | 0.0166 (16) |
| C14 | 0.0566 (18) | 0.075 (2) | 0.076 (2) | 0.0088 (15) | −0.0065 (15) | 0.0199 (17) |
| C15 | 0.0512 (16) | 0.0662 (19) | 0.0596 (16) | 0.0008 (14) | −0.0077 (12) | 0.0094 (14) |
| C16 | 0.0384 (13) | 0.0521 (17) | 0.0506 (15) | 0.0022 (11) | 0.0051 (11) | 0.0052 (12) |
| C17 | 0.0488 (15) | 0.0742 (18) | 0.0472 (15) | −0.0015 (13) | −0.0017 (12) | −0.0037 (14) |
| C18 | 0.0584 (18) | 0.090 (2) | 0.0445 (15) | −0.0034 (15) | 0.0081 (13) | 0.0028 (15) |
| C19 | 0.0471 (16) | 0.0785 (19) | 0.0590 (18) | −0.0057 (14) | 0.0125 (13) | 0.0006 (15) |
| C20 | 0.0393 (15) | 0.090 (2) | 0.0598 (18) | −0.0058 (14) | −0.0023 (13) | −0.0021 (15) |
| C21 | 0.0449 (14) | 0.084 (2) | 0.0444 (14) | −0.0048 (14) | 0.0024 (12) | 0.0023 (13) |
| C22 | 0.0574 (16) | 0.0549 (17) | 0.0607 (16) | 0.0017 (14) | 0.0018 (13) | −0.0073 (14) |
| C23 | 0.079 (2) | 0.0539 (18) | 0.077 (2) | 0.0009 (15) | 0.0049 (17) | −0.0124 (16) |
| C24 | 0.077 (2) | 0.071 (2) | 0.078 (2) | −0.0140 (17) | 0.0031 (17) | −0.0286 (18) |
| C25 | 0.0667 (19) | 0.082 (2) | 0.0669 (19) | −0.0056 (17) | −0.0090 (15) | −0.0162 (17) |
| C26 | 0.0552 (17) | 0.0651 (19) | 0.0653 (18) | −0.0018 (13) | −0.0048 (14) | −0.0078 (15) |
| C27 | 0.068 (2) | 0.067 (2) | 0.111 (3) | −0.0087 (16) | 0.0337 (19) | −0.0041 (18) |
| C28 | 0.088 (3) | 0.089 (3) | 0.135 (3) | −0.029 (2) | 0.051 (2) | −0.010 (2) |
| C29 | 0.0535 (19) | 0.123 (3) | 0.092 (2) | −0.020 (2) | 0.0220 (17) | −0.035 (2) |
| C30 | 0.0428 (16) | 0.103 (3) | 0.071 (2) | 0.0046 (16) | −0.0009 (14) | −0.0283 (18) |
| C31 | 0.0444 (15) | 0.0712 (19) | 0.0559 (16) | 0.0044 (13) | −0.0039 (12) | −0.0083 (14) |
| C32 | 0.090 (3) | 0.160 (4) | 0.112 (4) | 0.017 (3) | 0.015 (3) | −0.011 (3) |
| C33 | 0.074 (3) | 0.103 (3) | 0.140 (4) | 0.010 (2) | −0.021 (3) | −0.026 (3) |
| C34 | 0.114 (4) | 0.126 (3) | 0.088 (3) | 0.008 (3) | −0.011 (3) | −0.011 (2) |
| C35 | 0.096 (3) | 0.156 (4) | 0.095 (3) | 0.007 (3) | 0.012 (2) | 0.022 (3) |
| C36 | 0.071 (3) | 0.166 (4) | 0.118 (4) | 0.012 (3) | −0.012 (3) | 0.030 (3) |
| N1 | 0.0429 (11) | 0.0495 (13) | 0.0420 (12) | −0.0005 (9) | 0.0027 (9) | −0.0022 (10) |
| N2 | 0.0408 (11) | 0.0471 (12) | 0.0444 (12) | −0.0013 (9) | 0.0017 (9) | 0.0015 (9) |
| N3 | 0.0412 (11) | 0.0555 (13) | 0.0424 (11) | −0.0022 (9) | 0.0005 (9) | −0.0039 (10) |
| N4 | 0.0406 (11) | 0.0523 (14) | 0.0559 (13) | −0.0005 (10) | 0.0010 (10) | −0.0066 (10) |
| N5 | 0.0424 (12) | 0.0587 (14) | 0.0601 (13) | −0.0036 (11) | 0.0046 (10) | −0.0075 (11) |
| N6 | 0.094 (3) | 0.190 (4) | 0.096 (2) | 0.019 (3) | −0.019 (2) | 0.000 (2) |
| O1 | 0.0529 (10) | 0.0490 (10) | 0.0462 (10) | 0.0026 (8) | 0.0000 (8) | −0.0047 (8) |
| O2 | 0.0869 (13) | 0.0572 (11) | 0.0494 (10) | 0.0001 (10) | −0.0032 (9) | −0.0066 (9) |
| O3 | 0.145 (2) | 0.0689 (13) | 0.0739 (14) | −0.0529 (14) | −0.0469 (13) | 0.0201 (11) |
| O4 | 0.0517 (10) | 0.0515 (11) | 0.0537 (10) | 0.0002 (8) | −0.0100 (8) | 0.0003 (8) |
| Ni1—O1 | 2.0840 (16) | C18—H18 | 0.9300 |
| Ni1—O4 | 1.9750 (16) | C19—C20 | 1.371 (3) |
| Ni1—N2 | 2.0977 (19) | C19—H19 | 0.9300 |
| Ni1—N3 | 2.0882 (18) | C20—C21 | 1.334 (3) |
| Ni1—N4 | 2.180 (2) | C20—H20 | 0.9300 |
| Ni1—N5 | 2.1122 (19) | C21—N3 | 1.308 (3) |
| C1—C2 | 1.413 (3) | C21—H21 | 0.9300 |
| C1—C6 | 1.410 (3) | C22—N4 | 1.365 (3) |
| C1—C9 | 1.492 (3) | C22—C23 | 1.405 (3) |
| C2—C3 | 1.394 (3) | C22—H22 | 0.9300 |
| C2—H2 | 0.9300 | C23—C24 | 1.358 (4) |
| C3—C4 | 1.381 (4) | C23—H23 | 0.9300 |
| C3—H3 | 0.9300 | C24—C25 | 1.395 (4) |
| C4—C5 | 1.427 (4) | C24—H24 | 0.9300 |
| C4—H4 | 0.9300 | C25—C26 | 1.397 (4) |
| C5—C6 | 1.382 (3) | C25—H25 | 0.9300 |
| C5—H5 | 0.9300 | C26—N4 | 1.333 (3) |
| C6—C7 | 1.531 (3) | C26—H26 | 0.9300 |
| C7—O2 | 1.243 (3) | C27—N5 | 1.350 (3) |
| C7—C8 | 1.468 (3) | C27—C28 | 1.356 (4) |
| C8—N1 | 1.363 (3) | C27—H27 | 0.9300 |
| C8—C9 | 1.477 (3) | C28—C29 | 1.382 (4) |
| C9—O1 | 1.251 (3) | C28—H28 | 0.9300 |
| C10—O3 | 1.216 (3) | C29—C30 | 1.373 (4) |
| C10—C11 | 1.462 (3) | C29—H29 | 0.9300 |
| C10—N2 | 1.471 (3) | C30—C31 | 1.348 (3) |
| C11—C16 | 1.428 (3) | C30—H30 | 0.9300 |
| C11—C12 | 1.447 (3) | C31—N5 | 1.344 (3) |
| C12—C13 | 1.359 (4) | C31—H31 | 0.9300 |
| C12—H12 | 0.9300 | C32—N6 | 1.292 (5) |
| C13—C14 | 1.394 (4) | C32—C33 | 1.357 (5) |
| C13—H13 | 0.9300 | C32—H32 | 0.9300 |
| C14—C15 | 1.403 (4) | C33—C34 | 1.335 (5) |
| C14—H14 | 0.9300 | C33—H33 | 0.9300 |
| C15—C16 | 1.416 (3) | C34—C35 | 1.307 (5) |
| C15—H15 | 0.9300 | C34—H34 | 0.9300 |
| C16—O4 | 1.340 (3) | C35—C36 | 1.329 (5) |
| C17—N3 | 1.337 (3) | C35—H35 | 0.9300 |
| C17—C18 | 1.346 (3) | C36—N6 | 1.303 (5) |
| C17—H17 | 0.9300 | C36—H36 | 0.9300 |
| C18—C19 | 1.345 (3) | N1—N2 | 1.304 (2) |
| O4—Ni1—O1 | 175.52 (7) | C18—C19—H19 | 120.6 |
| O4—Ni1—N3 | 91.60 (7) | C20—C19—H19 | 120.6 |
| O1—Ni1—N3 | 92.40 (7) | C21—C20—C19 | 119.5 (2) |
| O4—Ni1—N2 | 89.32 (7) | C21—C20—H20 | 120.2 |
| O1—Ni1—N2 | 92.86 (7) | C19—C20—H20 | 120.2 |
| N3—Ni1—N2 | 87.64 (7) | N3—C21—C20 | 122.8 (2) |
| O4—Ni1—N5 | 91.34 (7) | N3—C21—H21 | 118.6 |
| O1—Ni1—N5 | 84.76 (7) | C20—C21—H21 | 118.6 |
| N3—Ni1—N5 | 175.99 (8) | N4—C22—C23 | 124.7 (3) |
| N2—Ni1—N5 | 89.67 (7) | N4—C22—H22 | 117.7 |
| O4—Ni1—N4 | 90.90 (7) | C23—C22—H22 | 117.7 |
| O1—Ni1—N4 | 87.05 (7) | C24—C23—C22 | 117.9 (3) |
| N3—Ni1—N4 | 90.48 (7) | C24—C23—H23 | 121.0 |
| N2—Ni1—N4 | 178.12 (7) | C22—C23—H23 | 121.0 |
| N5—Ni1—N4 | 92.20 (7) | C23—C24—C25 | 118.4 (3) |
| C6—C1—C2 | 122.1 (2) | C23—C24—H24 | 120.8 |
| C6—C1—C9 | 107.4 (2) | C25—C24—H24 | 120.8 |
| C2—C1—C9 | 130.5 (2) | C24—C25—C26 | 120.6 (3) |
| C3—C2—C1 | 118.2 (3) | C24—C25—H25 | 119.7 |
| C3—C2—H2 | 120.9 | C26—C25—H25 | 119.7 |
| C1—C2—H2 | 120.9 | N4—C26—C25 | 122.2 (3) |
| C4—C3—C2 | 119.8 (3) | N4—C26—H26 | 118.9 |
| C4—C3—H3 | 120.1 | C25—C26—H26 | 118.9 |
| C2—C3—H3 | 120.1 | N5—C27—C28 | 122.1 (3) |
| C3—C4—C5 | 122.3 (3) | N5—C27—H27 | 118.9 |
| C3—C4—H4 | 118.9 | C28—C27—H27 | 118.9 |
| C5—C4—H4 | 118.9 | C27—C28—C29 | 117.5 (3) |
| C6—C5—C4 | 118.3 (3) | C27—C28—H28 | 121.2 |
| C6—C5—H5 | 120.8 | C29—C28—H28 | 121.2 |
| C4—C5—H5 | 120.8 | C30—C29—C28 | 120.9 (3) |
| C5—C6—C1 | 119.3 (2) | C30—C29—H29 | 119.5 |
| C5—C6—C7 | 130.6 (2) | C28—C29—H29 | 119.5 |
| C1—C6—C7 | 110.1 (2) | C31—C30—C29 | 118.3 (3) |
| O2—C7—C8 | 127.5 (2) | C31—C30—H30 | 120.8 |
| O2—C7—C6 | 126.9 (2) | C29—C30—H30 | 120.8 |
| C8—C7—C6 | 105.6 (2) | N5—C31—C30 | 122.1 (3) |
| N1—C8—C7 | 119.4 (2) | N5—C31—H31 | 118.9 |
| N1—C8—C9 | 132.4 (2) | C30—C31—H31 | 118.9 |
| C7—C8—C9 | 108.0 (2) | N6—C32—C33 | 124.1 (4) |
| O1—C9—C8 | 127.9 (2) | N6—C32—H32 | 117.9 |
| O1—C9—C1 | 123.3 (2) | C33—C32—H32 | 117.9 |
| C8—C9—C1 | 108.82 (19) | C34—C33—C32 | 118.8 (4) |
| O3—C10—C11 | 119.7 (2) | C34—C33—H33 | 120.6 |
| O3—C10—N2 | 120.8 (2) | C32—C33—H33 | 120.6 |
| C11—C10—N2 | 119.4 (2) | C35—C34—C33 | 117.7 (4) |
| C16—C11—C12 | 120.3 (2) | C35—C34—H34 | 121.2 |
| C16—C11—C10 | 124.5 (2) | C33—C34—H34 | 121.2 |
| C12—C11—C10 | 115.2 (2) | C34—C35—C36 | 120.1 (4) |
| C13—C12—C11 | 122.8 (3) | C34—C35—H35 | 119.9 |
| C13—C12—H12 | 118.6 | C36—C35—H35 | 119.9 |
| C11—C12—H12 | 118.6 | N6—C36—C35 | 124.7 (4) |
| C12—C13—C14 | 117.2 (3) | N6—C36—H36 | 117.7 |
| C12—C13—H13 | 121.4 | C35—C36—H36 | 117.7 |
| C14—C13—H13 | 121.4 | N2—N1—C8 | 119.01 (19) |
| C13—C14—C15 | 121.9 (3) | N1—N2—C10 | 108.86 (18) |
| C13—C14—H14 | 119.0 | N1—N2—Ni1 | 126.31 (15) |
| C15—C14—H14 | 119.0 | C10—N2—Ni1 | 124.62 (15) |
| C14—C15—C16 | 122.7 (3) | C21—N3—C17 | 117.2 (2) |
| C14—C15—H15 | 118.6 | C21—N3—Ni1 | 120.16 (16) |
| C16—C15—H15 | 118.6 | C17—N3—Ni1 | 122.50 (16) |
| O4—C16—C15 | 118.0 (2) | C26—N4—C22 | 116.2 (2) |
| O4—C16—C11 | 127.1 (2) | C26—N4—Ni1 | 119.66 (18) |
| C15—C16—C11 | 115.0 (2) | C22—N4—Ni1 | 124.17 (17) |
| N3—C17—C18 | 123.6 (2) | C31—N5—C27 | 119.0 (2) |
| N3—C17—H17 | 118.2 | C31—N5—Ni1 | 117.98 (17) |
| C18—C17—H17 | 118.2 | C27—N5—Ni1 | 123.02 (18) |
| C19—C18—C17 | 118.1 (2) | C32—N6—C36 | 114.5 (4) |
| C19—C18—H18 | 120.9 | C9—O1—Ni1 | 118.72 (15) |
| C17—C18—H18 | 120.9 | C16—O4—Ni1 | 129.97 (15) |
| C18—C19—C20 | 118.9 (2) |
We are grateful to the National Natural Science Foundation of China (grant Nos. 20771048, 20431010, 20621091 and J0630962) for financial support.
Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Qiu, X.-Y., Fang, X.-N., Yang, S.-L., Liu, W.-S. & Zhu, H.-L. (2006). Acta Cryst. E62, o2687–o2688.
Qiu, X.-Y., Liu, W.-S. & Zhu, H.-L. (2007). Z. Anorg. Allg. Chem. 633, 1480-1484.
Qiu, X.-Y., Luo, Z.-G., Yang, S.-L. & Liu, W.-S. (2006). Acta Cryst. E62, o3531–o3532.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Westrip, S. P. (2008). publCIF. In preparation.
As part of an ongoing study on the structural characterization of Schiff-base compounds (Qiu, Fang et al., 2006; Qiu, Luo et al., 2006), the crystal structure of the title compound is reported here. In the molecule (Fig. 1), the NiII ion is six-coordinated by two oxygen atoms and one nitrogen atom from the schiff base ligand and three nitrogen atoms from three pyridine rings. One pyridine solvent molecule is not involved either in coordination to the NiII center or in classic hydrogen bonding to the compound. The Ni–O (phenolate) bond (1.975 Å) is the significantly shorter than other Ni–O (carbonyl) (2.084 Å) and Ni–N bonds (mean 2.120 Å), which suggests that the Ni–O (phenolate) bond is stronger than other bonds. From the crystal structure, the schiff base ligand and pyridine rings wrap around the NiII centre, forming an octahedral coordination (Qiu et al., 2007). A portion of the crystal packing of the compound is illustrated in Fig. 2.