Acta Cryst. (2009). E65, m20-m21 [ doi:10.1107/S1600536808040476 ]
In the title compound, [Ni(C16H10N3O3)2(C5H5N)2], the NiII cation is in a distorted octahedral NiN4O2 coordination by two independent bidentate 1-[(4-nitrophenyl)diazenyl]-2-naphtholate anions and two pyridine ligands. C-H
O interactions between aromatic rings and the O atoms of the nitro substituents build up a two-dimensional supramolecular arrangement parallel to (100).
To a mixture of 10.0 ml of MeOH and 10.0 ml of pyridine, 0.058 g (0.2 mmol) of 4-nitrophenylazo-2-naphthole was added with continuous stirring at room temperature. After stirring for 20 min, 0.025 g (0.1 mmol) of Ni(II) acetate were added. Stirring was maintained for 24 h. The solution was filtered off and red crystals of (I) with a block habit and up to 0.4 mm maximum size were obtained by slow evaporation of the mixture at room temperature. Melting point: 473 K; C, H, N analysis (%): calc., C, 62.94; H, 3.77; N, 13.98; found, C, 64.11; H, 3.91; N, 12.61.
The H atoms of the naphthyl, pyridine and phenyl rings were fixed geometrically at a distance of 0.93 Å and were refined in the riding model approximation with Uiso(H) = 1.2×Ueq of the parent C atom.
Data collection: COLLECT (Nonius, 1998); cell refinement: PHICHI (Duisenberg et al., 2000); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003) and WinGX (Farrugia, 1999).
![[Figure 1]](./wm2206fig1thm.gif)
| Fig. 1. ORTEP plot of the title molecule, (I). Displacement ellipsoids are drawn at the 50% probability level. |
![[Figure 2]](./wm2206fig2thm.gif)
| Fig. 2. View of the intermolecular H-bonding interactions and the formation of the two-dimensional arrangement. [Symmetry codes: (i) -x + 2, y - 1/2, -z - 1/2; (ii) -x + 1, y - 1/2, -z + 1/2.] |
| [Ni(C16H10N3O3)2(C5H5N)2] | F(000) = 1656 |
| Mr = 801.45 | Dx = 1.423 Mg m−3 |
| Monoclinic, P21/c | Melting point: 473 K |
| Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
| a = 11.719 (2) Å | Cell parameters from 217 reflections |
| b = 18.885 (4) Å | θ = 1.0–27.5° |
| c = 16.922 (3) Å | µ = 0.58 mm−1 |
| β = 93.04 (3)° | T = 295 K |
| V = 3740.0 (13) Å3 | Block, red |
| Z = 4 | 0.37 × 0.18 × 0.15 mm |
| Nonius KappaCCD diffractometer | 6566 independent reflections |
| Radiation source: fine-focus sealed tube | 4859 reflections with I > 2σ(I) |
| graphite | Rint = 0.076 |
| φ and ω scans | θmax = 25.0°, θmin = 2.8° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | h = −13→13 |
| Tmin = 0.814, Tmax = 0.918 | k = −22→22 |
| 64998 measured reflections | l = −20→20 |
| 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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.090 | H-atom parameters constrained |
| S = 1.05 | w = 1/[σ2(Fo2) + (0.0357P)2 + 1.6025P] where P = (Fo2 + 2Fc2)/3 |
| 6566 reflections | (Δ/σ)max < 0.001 |
| 514 parameters | Δρmax = 0.23 e Å−3 |
| 0 restraints | Δρmin = −0.24 e Å−3 |
| [Ni(C16H10N3O3)2(C5H5N)2] | V = 3740.0 (13) Å3 |
| Mr = 801.45 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 11.719 (2) Å | µ = 0.58 mm−1 |
| b = 18.885 (4) Å | T = 295 K |
| c = 16.922 (3) Å | 0.37 × 0.18 × 0.15 mm |
| β = 93.04 (3)° |
| Nonius KappaCCD diffractometer | 6566 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | 4859 reflections with I > 2σ(I) |
| Tmin = 0.814, Tmax = 0.918 | Rint = 0.076 |
| 64998 measured reflections | θmax = 25.0° |
| R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
| wR(F2) = 0.090 | Δρmax = 0.23 e Å−3 |
| S = 1.05 | Δρmin = −0.24 e Å−3 |
| 6566 reflections | Absolute structure: ? |
| 514 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
Experimental. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 5.9841 (0.0107) x + 0.5948 (0.0176) y + 14.0605 (0.0119) z = 4.0378 (0.0057) * 0.0370 (0.0010) N1 * -0.0652 (0.0015) N2 * 0.0496 (0.0015) C1 * -0.0087 (0.0015) C2 * -0.0127 (0.0010) O1 Rms deviation of fitted atoms = 0.0408 - 0.4462 (0.0069) x + 8.8584 (0.0115) y + 14.9440 (0.0093) z = 1.2966 (0.0053) Angle to previous plane (with approximate e.s.d.) = 41.11 (0.07) * 0.0666 (0.0009) O1 * -0.0633 (0.0009) N1 * 0.0616 (0.0008) O4 * -0.0623 (0.0009) N8 * -0.0026 (0.0008) Ni1 Rms deviation of fitted atoms = 0.0568 6.2807 (0.0104) x - 6.1779 (0.0201) y + 12.6704 (0.0108) z = 5.5919 (0.0111) Angle to previous plane (with approximate e.s.d.) = 59.14 (0.06) * -0.0118 (0.0011) O4 * 0.0423 (0.0016) C18 * -0.0623 (0.0015) C17 * 0.0507 (0.0015) N5 * -0.0189 (0.0010) N4 Rms deviation of fitted atoms = 0.0418 - 0.0859 (0.0070) x + 16.1355 (0.0106) y - 8.7731 (0.0106) z = 1.4081 (0.0053) Angle to previous plane (with approximate e.s.d.) = 46.54 (0.09) * 0.0058 (0.0009) O4 * 0.0056 (0.0010) N4 * 0.0063 (0.0009) O1 * 0.0060 (0.0009) N7 * -0.0236 (0.0008) Ni1 Rms deviation of fitted atoms = 0.0118 6.5874 (0.0126) x + 14.2991 (0.0164) y - 6.1291 (0.0186) z = 6.0049 (0.0088) Angle to previous plane (with approximate e.s.d.) = 35.34 (0.09) * 0.0044 (0.0017) N7 * -0.0069 (0.0020) C33 * 0.0029 (0.0023) C34 * 0.0033 (0.0025) C35 * -0.0056 (0.0023) C36 * 0.0019 (0.0019) C37 Rms deviation of fitted atoms = 0.0045 6.8092 (0.0117) x - 4.2913 (0.0191) y - 13.7284 (0.0134) z = 3.6963 (0.0099) Angle to previous plane (with approximate e.s.d.) = 65.50 (0.09) * 0.0087 (0.0016) N8 * -0.0004 (0.0019) C38 * -0.0074 (0.0021) C39 * 0.0071 (0.0020) C40 * 0.0011 (0.0019) C41 * -0.0092 (0.0018) C42 Rms deviation of fitted atoms = 0.0067 7.6103 (0.0099) x - 1.0403 (0.0194) y + 12.2331 (0.0135) z = 7.5132 (0.0060) Angle to previous plane (with approximate e.s.d.) = 78.29 (0.07) * -0.0081 (0.0017) C27 * 0.0104 (0.0018) C28 * -0.0020 (0.0018) C29 * -0.0088 (0.0018) C30 * 0.0109 (0.0019) C31 * -0.0025 (0.0019) C32 Rms deviation of fitted atoms = 0.0079 6.0882 (0.0095) x - 3.0287 (0.0105) y + 13.7154 (0.0112) z = 6.1985 (0.0098) Angle to previous plane (with approximate e.s.d.) = 10.66 (0.13) * 0.0072 (0.0020) C17 * -0.1226 (0.0020) C18 * 0.0188 (0.0022) C19 * 0.0637 (0.0024) C20 * 0.0353 (0.0026) C21 * -0.0368 (0.0028) C22 * -0.0666 (0.0033) C23 * -0.0092 (0.0031) C24 * 0.0452 (0.0026) C25 * 0.0652 (0.0024) C26 Rms deviation of fitted atoms = 0.0574 6.0989 (0.0089) x - 1.3127 (0.0101) y + 13.9139 (0.0107) z = 3.6881 (0.0050) Angle to previous plane (with approximate e.s.d.) = 5.25 (0.11) * -0.0019 (0.0019) C1 * 0.0685 (0.0019) C2 * -0.0202 (0.0021) C3 * -0.0339 (0.0022) C4 * -0.0136 (0.0024) C5 * 0.0221 (0.0025) C6 * 0.0381 (0.0028) C7 * -0.0039 (0.0027) C8 * -0.0255 (0.0024) C9 * -0.0297 (0.0023) C10 Rms deviation of fitted atoms = 0.0315 7.6507 (0.0101) x - 0.7993 (0.0215) y + 12.1938 (0.0139) z = 4.9408 (0.0114) Angle to previous plane (with approximate e.s.d.) = 9.47 (0.13) * 0.0100 (0.0017) C11 * -0.0050 (0.0019) C12 * -0.0055 (0.0021) C13 * 0.0110 (0.0019) C14 * -0.0058 (0.0018) C15 * -0.0048 (0.0018) C16 Rms deviation of fitted atoms = 0.0075 |
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 | 0.73654 (2) | 0.112500 (16) | 0.041889 (18) | 0.03358 (10) | |
| N1 | 0.71063 (15) | 0.21142 (10) | −0.02158 (11) | 0.0336 (4) | |
| N2 | 0.63714 (16) | 0.25763 (10) | 0.00047 (11) | 0.0370 (5) | |
| N3 | 1.0357 (2) | 0.33257 (17) | −0.21680 (16) | 0.0701 (8) | |
| N4 | 0.75644 (16) | 0.17270 (10) | 0.14908 (11) | 0.0379 (5) | |
| N5 | 0.81962 (17) | 0.22968 (11) | 0.15104 (12) | 0.0401 (5) | |
| N6 | 0.4055 (2) | 0.16963 (14) | 0.36697 (13) | 0.0531 (6) | |
| N7 | 0.73012 (17) | 0.05551 (10) | −0.06623 (12) | 0.0406 (5) | |
| N8 | 0.74895 (17) | 0.01201 (10) | 0.09784 (12) | 0.0386 (5) | |
| C1 | 0.54975 (19) | 0.23983 (13) | 0.04658 (13) | 0.0358 (5) | |
| C2 | 0.51196 (19) | 0.16895 (14) | 0.06152 (14) | 0.0373 (6) | |
| C3 | 0.4060 (2) | 0.16159 (16) | 0.10089 (15) | 0.0471 (6) | |
| H3 | 0.3751 | 0.1166 | 0.1067 | 0.056* | |
| C4 | 0.3506 (2) | 0.21795 (17) | 0.12949 (16) | 0.0543 (8) | |
| H4 | 0.2844 | 0.2103 | 0.1561 | 0.065* | |
| C5 | 0.3901 (2) | 0.28914 (16) | 0.12038 (15) | 0.0480 (7) | |
| C6 | 0.3342 (3) | 0.3474 (2) | 0.15296 (18) | 0.0678 (9) | |
| H6 | 0.2696 | 0.3398 | 0.1815 | 0.081* | |
| C7 | 0.3728 (3) | 0.4148 (2) | 0.1435 (2) | 0.0803 (11) | |
| H7 | 0.3356 | 0.4527 | 0.1662 | 0.096* | |
| C8 | 0.4683 (3) | 0.42665 (18) | 0.0997 (2) | 0.0732 (10) | |
| H8 | 0.4937 | 0.4727 | 0.0920 | 0.088* | |
| C9 | 0.5259 (3) | 0.37042 (15) | 0.06765 (18) | 0.0577 (8) | |
| H9 | 0.5904 | 0.3791 | 0.0394 | 0.069* | |
| C10 | 0.4883 (2) | 0.30047 (14) | 0.07722 (14) | 0.0426 (6) | |
| C11 | 0.78929 (19) | 0.24392 (12) | −0.07322 (13) | 0.0340 (5) | |
| C12 | 0.8024 (2) | 0.31680 (14) | −0.07792 (16) | 0.0482 (7) | |
| H12 | 0.7574 | 0.3463 | −0.0485 | 0.058* | |
| C13 | 0.8815 (3) | 0.34579 (15) | −0.12567 (17) | 0.0575 (8) | |
| H13 | 0.8900 | 0.3947 | −0.1287 | 0.069* | |
| C14 | 0.9481 (2) | 0.30173 (15) | −0.16898 (15) | 0.0465 (7) | |
| C15 | 0.9355 (2) | 0.22981 (14) | −0.16720 (15) | 0.0451 (6) | |
| H15 | 0.9798 | 0.2009 | −0.1978 | 0.054* | |
| C16 | 0.8561 (2) | 0.20082 (13) | −0.11915 (15) | 0.0415 (6) | |
| H16 | 0.8470 | 0.1519 | −0.1174 | 0.050* | |
| C17 | 0.9075 (2) | 0.23637 (13) | 0.10183 (14) | 0.0413 (6) | |
| C18 | 0.9558 (2) | 0.17932 (14) | 0.05833 (15) | 0.0425 (6) | |
| C19 | 1.0637 (2) | 0.19248 (16) | 0.02366 (17) | 0.0532 (7) | |
| H19 | 1.1029 | 0.1548 | 0.0024 | 0.064* | |
| C20 | 1.1091 (2) | 0.25816 (18) | 0.02127 (18) | 0.0605 (8) | |
| H20 | 1.1771 | 0.2647 | −0.0037 | 0.073* | |
| C21 | 1.0559 (2) | 0.31780 (17) | 0.05598 (17) | 0.0571 (8) | |
| C22 | 1.0988 (3) | 0.3870 (2) | 0.0470 (2) | 0.0810 (11) | |
| H22 | 1.1630 | 0.3941 | 0.0180 | 0.097* | |
| C23 | 1.0472 (4) | 0.4438 (2) | 0.0802 (3) | 0.0974 (14) | |
| H23 | 1.0756 | 0.4892 | 0.0734 | 0.117* | |
| C24 | 0.9519 (4) | 0.43321 (19) | 0.1244 (3) | 0.0902 (12) | |
| H24 | 0.9180 | 0.4717 | 0.1481 | 0.108* | |
| C25 | 0.9069 (3) | 0.36590 (16) | 0.13346 (19) | 0.0663 (9) | |
| H25 | 0.8424 | 0.3598 | 0.1624 | 0.080* | |
| C26 | 0.9579 (2) | 0.30722 (15) | 0.09933 (16) | 0.0495 (7) | |
| C27 | 0.6742 (2) | 0.17444 (13) | 0.20889 (13) | 0.0376 (6) | |
| C28 | 0.6336 (2) | 0.23743 (13) | 0.24103 (15) | 0.0418 (6) | |
| H28 | 0.6650 | 0.2805 | 0.2268 | 0.050* | |
| C29 | 0.5478 (2) | 0.23611 (14) | 0.29330 (15) | 0.0449 (6) | |
| H29 | 0.5202 | 0.2781 | 0.3138 | 0.054* | |
| C30 | 0.5028 (2) | 0.17145 (14) | 0.31523 (14) | 0.0416 (6) | |
| C31 | 0.5433 (2) | 0.10847 (14) | 0.28627 (14) | 0.0463 (6) | |
| H31 | 0.5140 | 0.0654 | 0.3026 | 0.056* | |
| C32 | 0.6281 (2) | 0.11035 (14) | 0.23263 (15) | 0.0466 (6) | |
| H32 | 0.6547 | 0.0682 | 0.2120 | 0.056* | |
| C33 | 0.6487 (2) | 0.06812 (15) | −0.12249 (16) | 0.0511 (7) | |
| H33 | 0.5897 | 0.0989 | −0.1115 | 0.061* | |
| C34 | 0.6486 (3) | 0.03716 (19) | −0.19646 (19) | 0.0736 (10) | |
| H34 | 0.5913 | 0.0475 | −0.2349 | 0.088* | |
| C35 | 0.7351 (3) | −0.0094 (2) | −0.2122 (2) | 0.0834 (12) | |
| H35 | 0.7370 | −0.0310 | −0.2615 | 0.100* | |
| C36 | 0.8178 (3) | −0.02345 (18) | −0.1546 (2) | 0.0731 (10) | |
| H36 | 0.8763 | −0.0552 | −0.1639 | 0.088* | |
| C37 | 0.8135 (2) | 0.00968 (14) | −0.08311 (17) | 0.0519 (7) | |
| H37 | 0.8707 | 0.0002 | −0.0443 | 0.062* | |
| C38 | 0.8368 (2) | −0.00533 (14) | 0.14751 (16) | 0.0485 (7) | |
| H38 | 0.8893 | 0.0297 | 0.1627 | 0.058* | |
| C39 | 0.8535 (3) | −0.07288 (16) | 0.17741 (18) | 0.0595 (8) | |
| H39 | 0.9154 | −0.0828 | 0.2123 | 0.071* | |
| C40 | 0.7765 (3) | −0.12535 (15) | 0.15457 (18) | 0.0580 (8) | |
| H40 | 0.7864 | −0.1715 | 0.1729 | 0.070* | |
| C41 | 0.6855 (2) | −0.10789 (14) | 0.10441 (17) | 0.0512 (7) | |
| H41 | 0.6321 | −0.1421 | 0.0884 | 0.061* | |
| C42 | 0.6738 (2) | −0.03930 (13) | 0.07789 (16) | 0.0444 (6) | |
| H42 | 0.6107 | −0.0280 | 0.0446 | 0.053* | |
| O1 | 0.56484 (13) | 0.11301 (9) | 0.04110 (10) | 0.0399 (4) | |
| O2 | 1.0358 (3) | 0.39692 (16) | −0.22459 (19) | 0.1256 (12) | |
| O3 | 1.1043 (2) | 0.29343 (15) | −0.24720 (15) | 0.0888 (8) | |
| O4 | 0.90854 (14) | 0.11845 (9) | 0.04779 (10) | 0.0449 (4) | |
| O5 | 0.3680 (2) | 0.11152 (12) | 0.38569 (14) | 0.0799 (7) | |
| O6 | 0.36631 (19) | 0.22562 (12) | 0.38958 (14) | 0.0758 (7) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Ni1 | 0.03349 (16) | 0.03100 (16) | 0.03668 (17) | −0.00179 (13) | 0.00593 (12) | −0.00190 (14) |
| N1 | 0.0334 (10) | 0.0355 (11) | 0.0326 (11) | −0.0007 (9) | 0.0084 (8) | −0.0021 (9) |
| N2 | 0.0360 (11) | 0.0394 (12) | 0.0358 (11) | 0.0018 (9) | 0.0035 (9) | −0.0009 (9) |
| N3 | 0.0730 (18) | 0.082 (2) | 0.0574 (16) | −0.0254 (16) | 0.0229 (14) | 0.0154 (15) |
| N4 | 0.0411 (11) | 0.0361 (11) | 0.0367 (11) | −0.0049 (9) | 0.0021 (9) | 0.0001 (9) |
| N5 | 0.0453 (12) | 0.0389 (12) | 0.0354 (11) | −0.0060 (10) | −0.0040 (9) | 0.0009 (9) |
| N6 | 0.0605 (15) | 0.0575 (16) | 0.0422 (13) | 0.0017 (13) | 0.0103 (11) | −0.0041 (12) |
| N7 | 0.0450 (12) | 0.0345 (11) | 0.0432 (12) | −0.0056 (9) | 0.0103 (10) | −0.0051 (10) |
| N8 | 0.0407 (11) | 0.0347 (11) | 0.0410 (12) | 0.0008 (9) | 0.0063 (9) | −0.0002 (9) |
| C1 | 0.0346 (13) | 0.0434 (14) | 0.0299 (13) | 0.0023 (11) | 0.0045 (10) | −0.0015 (11) |
| C2 | 0.0308 (12) | 0.0500 (15) | 0.0311 (13) | 0.0022 (11) | 0.0005 (10) | −0.0028 (11) |
| C3 | 0.0313 (13) | 0.0617 (18) | 0.0488 (16) | −0.0056 (12) | 0.0077 (11) | 0.0017 (14) |
| C4 | 0.0323 (14) | 0.089 (2) | 0.0428 (16) | 0.0034 (14) | 0.0072 (12) | −0.0034 (15) |
| C5 | 0.0369 (14) | 0.0677 (19) | 0.0392 (15) | 0.0134 (13) | 0.0006 (11) | −0.0089 (13) |
| C6 | 0.0507 (18) | 0.093 (3) | 0.060 (2) | 0.0191 (18) | 0.0077 (15) | −0.0226 (19) |
| C7 | 0.074 (2) | 0.084 (3) | 0.083 (3) | 0.032 (2) | 0.004 (2) | −0.036 (2) |
| C8 | 0.080 (2) | 0.057 (2) | 0.083 (2) | 0.0170 (17) | 0.0030 (19) | −0.0207 (18) |
| C9 | 0.0619 (18) | 0.0523 (18) | 0.0594 (19) | 0.0119 (14) | 0.0090 (15) | −0.0092 (14) |
| C10 | 0.0426 (14) | 0.0510 (16) | 0.0340 (14) | 0.0106 (12) | −0.0011 (11) | −0.0044 (12) |
| C11 | 0.0357 (13) | 0.0371 (13) | 0.0291 (12) | −0.0040 (10) | 0.0005 (10) | 0.0022 (10) |
| C12 | 0.0582 (17) | 0.0404 (15) | 0.0473 (16) | −0.0031 (12) | 0.0155 (13) | −0.0014 (12) |
| C13 | 0.072 (2) | 0.0411 (16) | 0.0603 (19) | −0.0136 (14) | 0.0173 (15) | 0.0090 (14) |
| C14 | 0.0456 (15) | 0.0587 (18) | 0.0358 (14) | −0.0105 (13) | 0.0074 (12) | 0.0098 (13) |
| C15 | 0.0435 (15) | 0.0518 (17) | 0.0413 (15) | 0.0018 (12) | 0.0131 (12) | 0.0049 (12) |
| C16 | 0.0430 (14) | 0.0362 (14) | 0.0464 (15) | −0.0019 (11) | 0.0128 (12) | 0.0032 (12) |
| C17 | 0.0412 (14) | 0.0465 (15) | 0.0353 (14) | −0.0087 (12) | −0.0053 (11) | 0.0041 (12) |
| C18 | 0.0353 (13) | 0.0508 (17) | 0.0409 (14) | −0.0035 (12) | −0.0032 (11) | 0.0084 (12) |
| C19 | 0.0363 (14) | 0.0658 (19) | 0.0575 (18) | −0.0043 (13) | 0.0024 (13) | 0.0042 (15) |
| C20 | 0.0383 (15) | 0.087 (2) | 0.0555 (18) | −0.0191 (16) | −0.0039 (13) | 0.0154 (17) |
| C21 | 0.0522 (17) | 0.066 (2) | 0.0515 (17) | −0.0233 (15) | −0.0131 (14) | 0.0154 (15) |
| C22 | 0.074 (2) | 0.080 (3) | 0.087 (3) | −0.040 (2) | −0.0172 (19) | 0.027 (2) |
| C23 | 0.117 (4) | 0.056 (2) | 0.116 (4) | −0.038 (2) | −0.020 (3) | 0.020 (2) |
| C24 | 0.114 (3) | 0.050 (2) | 0.104 (3) | −0.021 (2) | −0.008 (3) | −0.004 (2) |
| C25 | 0.081 (2) | 0.0481 (18) | 0.069 (2) | −0.0153 (16) | −0.0033 (17) | −0.0007 (15) |
| C26 | 0.0538 (16) | 0.0490 (17) | 0.0442 (16) | −0.0140 (13) | −0.0131 (13) | 0.0053 (13) |
| C27 | 0.0435 (14) | 0.0403 (14) | 0.0287 (12) | −0.0014 (11) | −0.0010 (10) | −0.0031 (11) |
| C28 | 0.0486 (15) | 0.0366 (14) | 0.0399 (15) | −0.0065 (11) | 0.0010 (12) | −0.0024 (11) |
| C29 | 0.0555 (16) | 0.0387 (15) | 0.0405 (15) | 0.0013 (12) | 0.0021 (12) | −0.0106 (12) |
| C30 | 0.0461 (14) | 0.0480 (16) | 0.0310 (13) | 0.0009 (12) | 0.0032 (11) | −0.0040 (12) |
| C31 | 0.0629 (17) | 0.0366 (14) | 0.0404 (14) | −0.0010 (13) | 0.0132 (12) | 0.0038 (12) |
| C32 | 0.0624 (17) | 0.0366 (14) | 0.0420 (14) | 0.0016 (13) | 0.0129 (12) | −0.0015 (12) |
| C33 | 0.0589 (17) | 0.0480 (17) | 0.0466 (16) | −0.0088 (13) | 0.0054 (14) | −0.0072 (13) |
| C34 | 0.080 (2) | 0.090 (3) | 0.0504 (19) | −0.027 (2) | −0.0005 (17) | −0.0147 (18) |
| C35 | 0.099 (3) | 0.091 (3) | 0.064 (2) | −0.031 (2) | 0.037 (2) | −0.042 (2) |
| C36 | 0.072 (2) | 0.069 (2) | 0.082 (2) | −0.0109 (18) | 0.037 (2) | −0.032 (2) |
| C37 | 0.0527 (16) | 0.0437 (16) | 0.0614 (18) | −0.0034 (13) | 0.0233 (14) | −0.0109 (14) |
| C38 | 0.0496 (16) | 0.0451 (16) | 0.0505 (16) | 0.0002 (12) | −0.0006 (13) | −0.0016 (13) |
| C39 | 0.0621 (19) | 0.0571 (19) | 0.0584 (19) | 0.0098 (15) | −0.0056 (15) | 0.0089 (15) |
| C40 | 0.074 (2) | 0.0377 (16) | 0.0638 (19) | 0.0050 (14) | 0.0153 (16) | 0.0099 (14) |
| C41 | 0.0599 (17) | 0.0389 (15) | 0.0557 (17) | −0.0084 (13) | 0.0102 (14) | 0.0021 (13) |
| C42 | 0.0449 (15) | 0.0391 (15) | 0.0495 (16) | −0.0038 (12) | 0.0060 (12) | 0.0010 (12) |
| O1 | 0.0348 (9) | 0.0402 (9) | 0.0453 (10) | −0.0050 (8) | 0.0083 (7) | −0.0032 (8) |
| O2 | 0.157 (3) | 0.083 (2) | 0.145 (3) | −0.0318 (19) | 0.088 (2) | 0.0334 (19) |
| O3 | 0.0725 (16) | 0.114 (2) | 0.0840 (18) | −0.0154 (15) | 0.0420 (14) | 0.0119 (16) |
| O4 | 0.0380 (9) | 0.0412 (10) | 0.0561 (11) | −0.0026 (8) | 0.0067 (8) | −0.0015 (9) |
| O5 | 0.0960 (17) | 0.0644 (15) | 0.0839 (16) | −0.0114 (13) | 0.0483 (13) | −0.0033 (13) |
| O6 | 0.0788 (15) | 0.0641 (14) | 0.0879 (17) | 0.0151 (12) | 0.0367 (13) | −0.0108 (12) |
| Ni1—N1 | 2.168 (2) | C16—H16 | 0.9300 |
| Ni1—N4 | 2.143 (2) | C17—C18 | 1.438 (4) |
| Ni1—N7 | 2.121 (2) | C17—C26 | 1.464 (3) |
| Ni1—N8 | 2.122 (2) | C18—O4 | 1.284 (3) |
| Ni1—O1 | 2.0116 (16) | C18—C19 | 1.443 (3) |
| Ni1—O4 | 2.0161 (17) | C19—C20 | 1.351 (4) |
| N1—N2 | 1.295 (3) | C19—H19 | 0.9300 |
| N1—C11 | 1.441 (3) | C20—C21 | 1.429 (4) |
| N2—C1 | 1.362 (3) | C20—H20 | 0.9300 |
| N3—O2 | 1.222 (4) | C21—C26 | 1.409 (4) |
| N3—O3 | 1.225 (4) | C22—C23 | 1.366 (5) |
| N3—C14 | 1.462 (3) | C22—C21 | 1.412 (4) |
| N4—N5 | 1.306 (3) | C22—H22 | 0.9300 |
| N4—C27 | 1.434 (3) | C23—C24 | 1.390 (6) |
| N5—C17 | 1.364 (3) | C23—H23 | 0.9300 |
| N6—O5 | 1.230 (3) | C24—C25 | 1.388 (4) |
| N6—C30 | 1.474 (3) | C24—H24 | 0.9300 |
| N7—C33 | 1.333 (3) | C25—C26 | 1.398 (4) |
| N7—C37 | 1.348 (3) | C25—H25 | 0.9300 |
| N8—C38 | 1.335 (3) | C27—C32 | 1.394 (3) |
| N8—C42 | 1.341 (3) | C27—C28 | 1.402 (3) |
| C1—C2 | 1.437 (3) | C28—C29 | 1.374 (3) |
| C1—C10 | 1.462 (3) | C28—H28 | 0.9300 |
| C2—O1 | 1.281 (3) | C29—C30 | 1.389 (3) |
| C2—C3 | 1.447 (3) | C29—H29 | 0.9300 |
| C3—C4 | 1.350 (4) | C30—C31 | 1.380 (3) |
| C3—H3 | 0.9300 | C31—C32 | 1.381 (3) |
| C4—C5 | 1.433 (4) | C31—H31 | 0.9300 |
| C4—H4 | 0.9300 | C32—H32 | 0.9300 |
| C5—C6 | 1.409 (4) | C33—C34 | 1.381 (4) |
| C5—C10 | 1.412 (4) | C33—H33 | 0.9300 |
| C6—C7 | 1.363 (5) | C34—C35 | 1.379 (5) |
| C6—H6 | 0.9300 | C34—H34 | 0.9300 |
| C7—H7 | 0.9300 | C35—C36 | 1.363 (5) |
| C8—C9 | 1.384 (4) | C35—H35 | 0.9300 |
| C8—C7 | 1.393 (5) | C36—C37 | 1.365 (4) |
| C8—H8 | 0.9300 | C36—H36 | 0.9300 |
| C9—C10 | 1.405 (4) | C37—H37 | 0.9300 |
| C9—H9 | 0.9300 | C38—C39 | 1.382 (4) |
| C11—C12 | 1.388 (3) | C38—H38 | 0.9300 |
| C11—C16 | 1.394 (3) | C39—C40 | 1.381 (4) |
| C12—C13 | 1.375 (4) | C39—H39 | 0.9300 |
| C12—H12 | 0.9300 | C40—C41 | 1.368 (4) |
| C13—C14 | 1.378 (4) | C40—H40 | 0.9300 |
| C13—H13 | 0.9300 | C41—C42 | 1.375 (4) |
| C14—C15 | 1.367 (4) | C41—H41 | 0.9300 |
| C15—C16 | 1.382 (3) | C42—H42 | 0.9300 |
| C15—H15 | 0.9300 | O6—N6 | 1.222 (3) |
| N1—N2—C1 | 122.0 (2) | C8—C7—H7 | 120.2 |
| N2—C1—C2 | 125.4 (2) | C8—C9—C10 | 120.9 (3) |
| N2—C1—C10 | 114.1 (2) | C8—C9—H9 | 119.5 |
| N2—N1—C11 | 110.14 (18) | C10—C9—H9 | 119.5 |
| N2—N1—Ni1 | 121.05 (14) | C9—C10—C5 | 118.1 (2) |
| N4—Ni1—N1 | 88.18 (7) | C9—C10—C1 | 122.2 (2) |
| N4—N5—C17 | 120.4 (2) | C5—C10—C1 | 119.7 (2) |
| N5—N4—C27 | 111.37 (19) | C12—C11—C16 | 118.7 (2) |
| N5—N4—Ni1 | 119.66 (15) | C12—C11—N1 | 122.3 (2) |
| N5—C17—C18 | 125.0 (2) | C16—C11—N1 | 119.0 (2) |
| N5—C17—C26 | 114.9 (2) | C13—C12—C11 | 120.6 (3) |
| N7—Ni1—N1 | 90.70 (8) | C13—C12—H12 | 119.7 |
| N7—Ni1—N4 | 175.45 (7) | C11—C12—H12 | 119.7 |
| N7—Ni1—N8 | 85.96 (8) | C12—C13—C14 | 119.4 (3) |
| N7—C37—C36 | 122.9 (3) | C12—C13—H13 | 120.3 |
| N7—C37—H37 | 118.5 | C14—C13—H13 | 120.3 |
| N7—C33—C34 | 122.5 (3) | C15—C14—C13 | 121.6 (2) |
| N7—C33—H33 | 118.7 | C15—C14—N3 | 119.2 (3) |
| N8—C42—C41 | 123.1 (3) | C13—C14—N3 | 119.2 (3) |
| N8—C42—H42 | 118.5 | C14—C15—C16 | 118.9 (2) |
| N8—C38—C39 | 123.1 (3) | C14—C15—H15 | 120.5 |
| N8—C38—H38 | 118.5 | C16—C15—H15 | 120.5 |
| N8—Ni1—N1 | 174.80 (8) | C15—C16—C11 | 120.8 (2) |
| N8—Ni1—N4 | 95.45 (8) | C15—C16—H16 | 119.6 |
| O1—Ni1—N4 | 93.84 (7) | C11—C16—H16 | 119.6 |
| O1—Ni1—O4 | 175.75 (7) | C18—C17—C26 | 120.0 (2) |
| O1—Ni1—N7 | 90.40 (8) | C17—C18—C19 | 117.1 (2) |
| O1—Ni1—N8 | 92.99 (7) | C20—C19—C18 | 121.7 (3) |
| O1—Ni1—N1 | 83.04 (7) | C20—C19—H19 | 119.2 |
| O1—C2—C1 | 124.2 (2) | C18—C19—H19 | 119.2 |
| O1—C2—C3 | 119.0 (2) | C19—C20—C21 | 122.0 (3) |
| O2—N3—O3 | 123.4 (3) | C19—C20—H20 | 119.0 |
| O2—N3—C14 | 117.4 (3) | C21—C20—H20 | 119.0 |
| O3—N3—C14 | 119.2 (3) | C26—C21—C22 | 119.5 (3) |
| O4—Ni1—N4 | 82.23 (8) | C26—C21—C20 | 119.2 (3) |
| O4—Ni1—N7 | 93.47 (8) | C22—C21—C20 | 121.3 (3) |
| O4—Ni1—N8 | 89.03 (7) | C25—C26—C21 | 118.7 (3) |
| O4—Ni1—N1 | 95.16 (7) | C25—C26—C17 | 122.0 (3) |
| O4—C18—C17 | 124.3 (2) | C21—C26—C17 | 119.1 (3) |
| O4—C18—C19 | 118.6 (2) | C32—C27—C28 | 118.7 (2) |
| O5—N6—C30 | 118.2 (2) | C32—C27—N4 | 118.0 (2) |
| O6—N6—O5 | 123.1 (2) | C28—C27—N4 | 123.2 (2) |
| O6—N6—C30 | 118.8 (2) | C29—C28—C27 | 120.6 (2) |
| C11—N1—Ni1 | 126.17 (14) | C29—C28—H28 | 119.7 |
| C27—N4—Ni1 | 124.23 (15) | C27—C28—H28 | 119.7 |
| C9—C8—C7 | 120.5 (3) | C28—C29—C30 | 119.3 (2) |
| C9—C8—H8 | 119.7 | C28—C29—H29 | 120.4 |
| C7—C8—H8 | 119.7 | C30—C29—H29 | 120.4 |
| C23—C22—C21 | 120.9 (4) | C31—C30—C29 | 121.3 (2) |
| C23—C22—H22 | 119.5 | C31—C30—N6 | 118.8 (2) |
| C21—C22—H22 | 119.5 | C29—C30—N6 | 119.7 (2) |
| C22—C23—C24 | 119.7 (3) | C30—C31—C32 | 119.0 (2) |
| C22—C23—H23 | 120.2 | C30—C31—H31 | 120.5 |
| C24—C23—H23 | 120.2 | C32—C31—H31 | 120.5 |
| C25—C24—C23 | 120.8 (4) | C31—C32—C27 | 121.0 (2) |
| C25—C24—H24 | 119.6 | C31—C32—H32 | 119.5 |
| C23—C24—H24 | 119.6 | C27—C32—H32 | 119.5 |
| C24—C25—C26 | 120.4 (3) | C34—C33—H33 | 118.7 |
| C24—C25—H25 | 119.8 | C35—C34—C33 | 118.6 (3) |
| C26—C25—H25 | 119.8 | C35—C34—H34 | 120.7 |
| C33—N7—C37 | 117.6 (2) | C33—C34—H34 | 120.7 |
| C33—N7—Ni1 | 121.11 (17) | C36—C35—C34 | 119.2 (3) |
| C37—N7—Ni1 | 121.06 (19) | C36—C35—H35 | 120.4 |
| C38—N8—C42 | 117.1 (2) | C34—C35—H35 | 120.4 |
| C38—N8—Ni1 | 122.17 (17) | C35—C36—C37 | 119.1 (3) |
| C42—N8—Ni1 | 120.36 (17) | C35—C36—H36 | 120.5 |
| C2—C1—C10 | 120.4 (2) | C37—C36—H36 | 120.5 |
| C1—C2—C3 | 116.8 (2) | C36—C37—H37 | 118.5 |
| C4—C3—C2 | 122.0 (3) | C39—C38—H38 | 118.5 |
| C4—C3—H3 | 119.0 | C40—C39—C38 | 118.8 (3) |
| C2—C3—H3 | 119.0 | C40—C39—H39 | 120.6 |
| C3—C4—C5 | 122.5 (2) | C38—C39—H39 | 120.6 |
| C3—C4—H4 | 118.7 | C41—C40—C39 | 118.5 (3) |
| C5—C4—H4 | 118.7 | C41—C40—H40 | 120.8 |
| C6—C5—C10 | 119.5 (3) | C39—C40—H40 | 120.8 |
| C6—C5—C4 | 122.1 (3) | C40—C41—C42 | 119.4 (3) |
| C10—C5—C4 | 118.3 (2) | C40—C41—H41 | 120.3 |
| C7—C6—C5 | 121.3 (3) | C42—C41—H41 | 120.3 |
| C7—C6—H6 | 119.3 | C41—C42—H42 | 118.5 |
| C5—C6—H6 | 119.3 | C2—O1—Ni1 | 120.00 (14) |
| C6—C7—C8 | 119.5 (3) | C18—O4—Ni1 | 118.64 (15) |
| C6—C7—H7 | 120.2 | ||
| C21—C22—C23—C24 | 0.8 (6) | O2—N3—C14—C13 | −9.6 (4) |
| C22—C23—C24—C25 | −1.6 (6) | O3—N3—C14—C13 | 170.8 (3) |
| C23—C24—C25—C26 | 1.1 (6) | C13—C14—C15—C16 | −1.7 (4) |
| O1—Ni1—N1—N2 | 43.27 (17) | N3—C14—C15—C16 | 177.1 (2) |
| O4—Ni1—N1—N2 | −132.86 (17) | C14—C15—C16—C11 | 0.1 (4) |
| N7—Ni1—N1—N2 | 133.59 (17) | C12—C11—C16—C15 | 1.4 (4) |
| N4—Ni1—N1—N2 | −50.82 (17) | N1—C11—C16—C15 | −177.6 (2) |
| O1—Ni1—N1—C11 | −156.98 (18) | N4—N5—C17—C18 | −14.8 (4) |
| O4—Ni1—N1—C11 | 26.89 (18) | N4—N5—C17—C26 | 169.2 (2) |
| N7—Ni1—N1—C11 | −66.66 (18) | N5—C17—C18—O4 | 14.6 (4) |
| N4—Ni1—N1—C11 | 108.92 (18) | C26—C17—C18—O4 | −169.7 (2) |
| C11—N1—N2—C1 | 176.8 (2) | N5—C17—C18—C19 | −166.3 (2) |
| Ni1—N1—N2—C1 | −20.5 (3) | C26—C17—C18—C19 | 9.4 (3) |
| O1—Ni1—N4—N5 | −127.58 (17) | O4—C18—C19—C20 | 169.1 (3) |
| O4—Ni1—N4—N5 | 50.77 (17) | C17—C18—C19—C20 | −10.0 (4) |
| N8—Ni1—N4—N5 | 139.04 (17) | C18—C19—C20—C21 | 2.9 (4) |
| N1—Ni1—N4—N5 | −44.68 (17) | C23—C22—C21—C26 | 0.5 (5) |
| O1—Ni1—N4—C27 | 25.88 (19) | C23—C22—C21—C20 | 179.8 (3) |
| O4—Ni1—N4—C27 | −155.77 (19) | C19—C20—C21—C26 | 5.0 (4) |
| N8—Ni1—N4—C27 | −67.50 (19) | C19—C20—C21—C22 | −174.3 (3) |
| N1—Ni1—N4—C27 | 108.78 (18) | C24—C25—C26—C21 | 0.3 (5) |
| C27—N4—N5—C17 | 176.1 (2) | C24—C25—C26—C17 | −174.7 (3) |
| Ni1—N4—N5—C17 | −27.2 (3) | C22—C21—C26—C25 | −1.1 (4) |
| O1—Ni1—N7—C33 | 36.6 (2) | C20—C21—C26—C25 | 179.6 (3) |
| O4—Ni1—N7—C33 | −141.64 (19) | C22—C21—C26—C17 | 174.0 (3) |
| N8—Ni1—N7—C33 | 129.6 (2) | C20—C21—C26—C17 | −5.3 (4) |
| N1—Ni1—N7—C33 | −46.4 (2) | N5—C17—C26—C25 | −10.9 (4) |
| O1—Ni1—N7—C37 | −149.05 (19) | C18—C17—C26—C25 | 172.9 (3) |
| O4—Ni1—N7—C37 | 32.70 (19) | N5—C17—C26—C21 | 174.1 (2) |
| N8—Ni1—N7—C37 | −56.08 (19) | C18—C17—C26—C21 | −2.0 (4) |
| N1—Ni1—N7—C37 | 127.91 (19) | N5—N4—C27—C32 | −158.6 (2) |
| O1—Ni1—N8—C38 | −147.84 (19) | Ni1—N4—C27—C32 | 46.0 (3) |
| O4—Ni1—N8—C38 | 28.4 (2) | N5—N4—C27—C28 | 25.2 (3) |
| N7—Ni1—N8—C38 | 122.0 (2) | Ni1—N4—C27—C28 | −130.2 (2) |
| N4—Ni1—N8—C38 | −53.7 (2) | C32—C27—C28—C29 | −1.7 (4) |
| O1—Ni1—N8—C42 | 39.14 (19) | N4—C27—C28—C29 | 174.5 (2) |
| O4—Ni1—N8—C42 | −144.60 (19) | C27—C28—C29—C30 | 1.2 (4) |
| N7—Ni1—N8—C42 | −51.05 (19) | C28—C29—C30—C31 | 0.7 (4) |
| N4—Ni1—N8—C42 | 133.29 (18) | C28—C29—C30—N6 | −175.9 (2) |
| N1—N2—C1—C2 | −14.7 (4) | O6—N6—C30—C31 | −176.6 (2) |
| N1—N2—C1—C10 | 169.5 (2) | O5—N6—C30—C31 | 3.7 (4) |
| N2—C1—C2—O1 | 9.0 (4) | O6—N6—C30—C29 | 0.0 (4) |
| C10—C1—C2—O1 | −175.5 (2) | O5—N6—C30—C29 | −179.6 (3) |
| N2—C1—C2—C3 | −169.8 (2) | C29—C30—C31—C32 | −1.9 (4) |
| C10—C1—C2—C3 | 5.7 (3) | N6—C30—C31—C32 | 174.7 (2) |
| O1—C2—C3—C4 | 174.7 (2) | C30—C31—C32—C27 | 1.3 (4) |
| C1—C2—C3—C4 | −6.4 (4) | C28—C27—C32—C31 | 0.5 (4) |
| C2—C3—C4—C5 | 2.4 (4) | N4—C27—C32—C31 | −175.9 (2) |
| C3—C4—C5—C6 | −177.6 (3) | C37—N7—C33—C34 | −1.2 (4) |
| C3—C4—C5—C10 | 2.4 (4) | Ni1—N7—C33—C34 | 173.4 (2) |
| C10—C5—C6—C7 | 0.2 (4) | N7—C33—C34—C35 | 1.0 (5) |
| C4—C5—C6—C7 | −179.9 (3) | C33—C34—C35—C36 | 0.0 (5) |
| C5—C6—C7—C8 | 1.1 (5) | C34—C35—C36—C37 | −0.8 (5) |
| C9—C8—C7—C6 | −1.7 (5) | C33—N7—C37—C36 | 0.3 (4) |
| C7—C8—C9—C10 | 1.1 (5) | Ni1—N7—C37—C36 | −174.2 (2) |
| C8—C9—C10—C5 | 0.1 (4) | C35—C36—C37—N7 | 0.7 (5) |
| C8—C9—C10—C1 | −177.7 (3) | C42—N8—C38—C39 | 1.0 (4) |
| C6—C5—C10—C9 | −0.8 (4) | Ni1—N8—C38—C39 | −172.3 (2) |
| C4—C5—C10—C9 | 179.3 (2) | N8—C38—C39—C40 | 0.6 (4) |
| C6—C5—C10—C1 | 177.1 (2) | C38—C39—C40—C41 | −1.3 (4) |
| C4—C5—C10—C1 | −2.9 (4) | C39—C40—C41—C42 | 0.5 (4) |
| N2—C1—C10—C9 | −7.5 (4) | C38—N8—C42—C41 | −1.8 (4) |
| C2—C1—C10—C9 | 176.5 (2) | Ni1—N8—C42—C41 | 171.5 (2) |
| N2—C1—C10—C5 | 174.8 (2) | C40—C41—C42—N8 | 1.1 (4) |
| C2—C1—C10—C5 | −1.2 (3) | C1—C2—O1—Ni1 | 34.0 (3) |
| N2—N1—C11—C12 | 17.2 (3) | C3—C2—O1—Ni1 | −147.22 (18) |
| Ni1—N1—C11—C12 | −144.4 (2) | N7—Ni1—O1—C2 | −138.84 (17) |
| N2—N1—C11—C16 | −163.9 (2) | N8—Ni1—O1—C2 | 135.18 (17) |
| Ni1—N1—C11—C16 | 34.5 (3) | N4—Ni1—O1—C2 | 39.51 (18) |
| C16—C11—C12—C13 | −1.4 (4) | N1—Ni1—O1—C2 | −48.18 (17) |
| N1—C11—C12—C13 | 177.5 (2) | C17—C18—O4—Ni1 | 30.8 (3) |
| C11—C12—C13—C14 | −0.1 (4) | C19—C18—O4—Ni1 | −148.24 (19) |
| C12—C13—C14—C15 | 1.7 (4) | N7—Ni1—O4—C18 | 128.08 (18) |
| C12—C13—C14—N3 | −177.1 (3) | N8—Ni1—O4—C18 | −146.03 (18) |
| O2—N3—C14—C15 | 171.5 (3) | N4—Ni1—O4—C18 | −50.39 (18) |
| O3—N3—C14—C15 | −8.0 (4) | N1—Ni1—O4—C18 | 37.06 (18) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C36—H36···O2i | 0.93 | 2.38 | 3.124 (5) | 137 |
| C41—H41···O6ii | 0.93 | 2.53 | 3.205 (4) | 130 |
| Symmetry codes: (i) −x+2, y−1/2, −z−1/2; (ii) −x+1, y−1/2, −z+1/2. |
| Ni1—N1 | 2.168 (2) | Ni1—N8 | 2.122 (2) |
| Ni1—N4 | 2.143 (2) | Ni1—O1 | 2.0116 (16) |
| Ni1—N7 | 2.121 (2) | Ni1—O4 | 2.0161 (17) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C36—H36···O2i | 0.93 | 2.38 | 3.124 (5) | 137 |
| C41—H41···O6ii | 0.93 | 2.53 | 3.205 (4) | 130 |
| Symmetry codes: (i) −x+2, y−1/2, −z−1/2; (ii) −x+1, y−1/2, −z+1/2. |
X-ray diffraction measurements were performed in the Laboratório de Difração de Raios X at the Universidade Federal Fluminense (LDRX-UFF), Niterói, Brazil. The authors thank Professor J. A. P. Bonapace for the initial reagents, CAPES, CNPq and FAPERJ for financial support, and the co-editor for his help in the improvement of the manuscript.
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Metal complexes with azo ligands show interesting chemical and physical properties and are of interest as new materials, for example in bioinorganic and coordination chemistry, as well as in biological systems which can lead to the development of new products with specific properties (Carella et al., 2007; Kulikovska et al., 2007; Patnaik et al., 2007; Leng et al., 2001). In this work the structure of the title molecule, [Ni(C16H10N3O3)2(C5H5N)2], (I) is reported.
Fig. 1 shows the molecular structure of compound (I). The NiII cation is octahedrally coordinated by four N and two O atoms with only slight distortion from the ideal coordination geometry. The two independent 1-[(4-nitrophenyl)diazenyl]-2-naphtholate ligands are bidentate and provide each one N atom from the azene moiety and one naphtolate O atom. The coordination is completed by the two pyridine N atoms. The Ni—N and Ni—O distances (Table 1) are in the typical ranges and like all other interatomic distances are in good agreement with literature data (Abildgaard et al., 2006).
The crystal packing is accomplished by two non-classical intermolecular C—H···O hydrogen bonds (Jeffrey & Saenger, 1991), forming a two-dimensional arrangement parallel to (100) (Fig. 2).