metal-organic compounds
The NiII atom in the title complex, [Ni(C11H14NO4)2]·C5H5N, is chelated by a terdentate Schiff base anion in a slightly disotorted octahedral geometry. One of the two coordinated hydroxyl groups forms a hydrogen bond to the pyridine solvent while other hydroxyl groups are engaged in intermolecular hydrogen bonding, forming a two-dimensional layer.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806038712/lh2190sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806038712/lh2190Isup2.hkl |
CCDC reference: 624924
Computing details top
Data collection: APEXII (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.
Bis[1,3-dihydroxy-2-hydroxymethyl-2-(salicylidimino)propane-
κ3N,O,O']nickel(II) pyridine solvate top
Crystal data top
[Ni(C11H14NO4)2]·C5H5N | F(000) = 1232 |
Mr = 586.27 | Dx = 1.496 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 8970 reflections |
a = 11.1164 (2) Å | θ = 2.6–34.0° |
b = 11.5298 (2) Å | µ = 0.80 mm−1 |
c = 21.1733 (3) Å | T = 173 K |
β = 106.390 (1)° | Prism, green |
V = 2603.50 (7) Å3 | 0.35 × 0.30 × 0.20 mm |
Z = 4 |
Data collection top
Bruker APEXII area-detector diffractometer | 5978 independent reflections |
Radiation source: fine-focus sealed tube | 4697 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.058 |
φ and ω scans | θmax = 27.5°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −14→14 |
Tmin = 0.650, Tmax = 0.856 | k = −14→14 |
38368 measured reflections | l = −27→27 |
Refinement top
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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.108 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0533P)2 + 1.3685P] where P = (Fo2 + 2Fc2)/3 |
5978 reflections | (Δ/σ)max = 0.001 |
376 parameters | Δρmax = 0.77 e Å−3 |
6 restraints | Δρmin = −0.81 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Ni1 | 0.46931 (3) | 0.37950 (2) | 0.740615 (14) | 0.00882 (9) | |
O1 | 0.49288 (14) | 0.48112 (13) | 0.81994 (8) | 0.0125 (3) | |
O2 | 0.46963 (15) | 0.25602 (14) | 0.66972 (8) | 0.0138 (3) | |
H2O | 0.431 (3) | 0.261 (3) | 0.6289 (6) | 0.043 (10)* | |
O3 | 0.81226 (15) | 0.12857 (14) | 0.78907 (8) | 0.0144 (3) | |
H3O | 0.8810 (17) | 0.092 (2) | 0.8001 (15) | 0.035 (9)* | |
O4 | 0.81615 (15) | 0.44448 (14) | 0.69200 (8) | 0.0157 (4) | |
H4O | 0.784 (3) | 0.5054 (18) | 0.7024 (16) | 0.042 (10)* | |
O5 | 0.47733 (14) | 0.51597 (13) | 0.68170 (8) | 0.0131 (3) | |
O6 | 0.41994 (14) | 0.23602 (13) | 0.79388 (8) | 0.0120 (3) | |
H6O | 0.404 (3) | 0.1778 (18) | 0.7688 (12) | 0.034 (9)* | |
O7 | 0.06341 (16) | 0.49956 (14) | 0.74492 (9) | 0.0190 (4) | |
H7O | −0.0102 (17) | 0.471 (3) | 0.7312 (18) | 0.058 (12)* | |
O8 | 0.17953 (16) | 0.15501 (14) | 0.69602 (9) | 0.0175 (4) | |
H8O | 0.130 (2) | 0.0975 (19) | 0.6905 (16) | 0.036 (9)* | |
N1 | 0.65578 (17) | 0.34210 (16) | 0.76434 (9) | 0.0095 (4) | |
N2 | 0.27935 (17) | 0.39446 (15) | 0.71492 (9) | 0.0102 (4) | |
N3 | 0.32652 (19) | 0.27660 (18) | 0.54980 (10) | 0.0171 (4) | |
C1 | 0.5940 (2) | 0.48868 (19) | 0.87003 (11) | 0.0120 (4) | |
C2 | 0.5875 (2) | 0.5497 (2) | 0.92716 (12) | 0.0178 (5) | |
H2 | 0.5101 | 0.5837 | 0.9278 | 0.021* | |
C3 | 0.6892 (2) | 0.5612 (2) | 0.98152 (12) | 0.0211 (5) | |
H3 | 0.6807 | 0.6020 | 1.0190 | 0.025* | |
C4 | 0.8056 (2) | 0.5131 (2) | 0.98209 (12) | 0.0209 (5) | |
H4 | 0.8763 | 0.5216 | 1.0194 | 0.025* | |
C5 | 0.8149 (2) | 0.4538 (2) | 0.92776 (12) | 0.0165 (5) | |
H5 | 0.8935 | 0.4210 | 0.9282 | 0.020* | |
C6 | 0.7123 (2) | 0.43944 (19) | 0.87096 (11) | 0.0121 (4) | |
C7 | 0.7363 (2) | 0.37205 (18) | 0.81811 (11) | 0.0120 (4) | |
H7 | 0.8203 | 0.3475 | 0.8239 | 0.014* | |
C8 | 0.6955 (2) | 0.27740 (19) | 0.71332 (11) | 0.0108 (4) | |
C9 | 0.5862 (2) | 0.19723 (19) | 0.67899 (11) | 0.0130 (5) | |
H9A | 0.5954 | 0.1726 | 0.6358 | 0.016* | |
H9B | 0.5878 | 0.1270 | 0.7061 | 0.016* | |
C10 | 0.8155 (2) | 0.20684 (19) | 0.73759 (11) | 0.0127 (4) | |
H10A | 0.8293 | 0.1623 | 0.7003 | 0.015* | |
H10B | 0.8872 | 0.2605 | 0.7536 | 0.015* | |
C11 | 0.7184 (2) | 0.36500 (19) | 0.66312 (11) | 0.0136 (5) | |
H11A | 0.7402 | 0.3224 | 0.6273 | 0.016* | |
H11B | 0.6401 | 0.4087 | 0.6435 | 0.016* | |
C12 | 0.3870 (2) | 0.55045 (18) | 0.63027 (11) | 0.0115 (4) | |
C13 | 0.4145 (2) | 0.6317 (2) | 0.58617 (12) | 0.0159 (5) | |
H13 | 0.4974 | 0.6611 | 0.5948 | 0.019* | |
C14 | 0.3238 (2) | 0.6693 (2) | 0.53082 (12) | 0.0190 (5) | |
H14 | 0.3456 | 0.7232 | 0.5020 | 0.023* | |
C15 | 0.2011 (2) | 0.6290 (2) | 0.51687 (12) | 0.0184 (5) | |
H15 | 0.1391 | 0.6541 | 0.4785 | 0.022* | |
C16 | 0.1714 (2) | 0.55211 (19) | 0.55976 (11) | 0.0146 (5) | |
H16 | 0.0874 | 0.5252 | 0.5506 | 0.018* | |
C17 | 0.2608 (2) | 0.51181 (18) | 0.61672 (11) | 0.0116 (4) | |
C18 | 0.2140 (2) | 0.43931 (18) | 0.66052 (11) | 0.0113 (4) | |
H18 | 0.1266 | 0.4235 | 0.6478 | 0.014* | |
C19 | 0.2135 (2) | 0.33486 (19) | 0.75744 (11) | 0.0119 (4) | |
C20 | 0.3142 (2) | 0.2765 (2) | 0.81415 (11) | 0.0140 (5) | |
H20A | 0.3436 | 0.3328 | 0.8506 | 0.017* | |
H20B | 0.2760 | 0.2101 | 0.8311 | 0.017* | |
C21 | 0.1473 (2) | 0.4255 (2) | 0.79006 (12) | 0.0148 (5) | |
H21A | 0.1004 | 0.3841 | 0.8166 | 0.018* | |
H21B | 0.2120 | 0.4737 | 0.8206 | 0.018* | |
C22 | 0.1184 (2) | 0.24409 (19) | 0.72160 (12) | 0.0141 (5) | |
H22A | 0.0758 | 0.2101 | 0.7525 | 0.017* | |
H22B | 0.0541 | 0.2814 | 0.6852 | 0.017* | |
C23 | 0.3500 (2) | 0.3429 (2) | 0.50287 (12) | 0.0194 (5) | |
H23 | 0.4314 | 0.3752 | 0.5103 | 0.023* | |
C24 | 0.2610 (3) | 0.3664 (2) | 0.44413 (13) | 0.0241 (6) | |
H24 | 0.2807 | 0.4142 | 0.4119 | 0.029* | |
C25 | 0.1429 (3) | 0.3192 (2) | 0.43324 (13) | 0.0271 (6) | |
H25 | 0.0801 | 0.3330 | 0.3930 | 0.033* | |
C26 | 0.1177 (2) | 0.2518 (2) | 0.48158 (13) | 0.0261 (6) | |
H26 | 0.0368 | 0.2190 | 0.4755 | 0.031* | |
C27 | 0.2117 (2) | 0.2323 (2) | 0.53912 (13) | 0.0207 (5) | |
H27 | 0.1939 | 0.1857 | 0.5723 | 0.025* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.00519 (14) | 0.00846 (14) | 0.01264 (15) | 0.00028 (10) | 0.00226 (10) | 0.00040 (11) |
O1 | 0.0082 (8) | 0.0120 (8) | 0.0163 (8) | 0.0013 (6) | 0.0021 (6) | −0.0012 (6) |
O2 | 0.0078 (8) | 0.0171 (8) | 0.0148 (8) | 0.0020 (6) | 0.0005 (6) | −0.0019 (7) |
O3 | 0.0089 (8) | 0.0126 (8) | 0.0216 (9) | 0.0042 (6) | 0.0040 (7) | 0.0048 (6) |
O4 | 0.0109 (8) | 0.0115 (8) | 0.0257 (9) | −0.0014 (6) | 0.0068 (7) | 0.0004 (7) |
O5 | 0.0084 (8) | 0.0131 (8) | 0.0165 (8) | −0.0007 (6) | 0.0013 (6) | 0.0034 (6) |
O6 | 0.0083 (8) | 0.0099 (7) | 0.0178 (8) | 0.0011 (6) | 0.0036 (6) | 0.0007 (6) |
O7 | 0.0114 (9) | 0.0125 (8) | 0.0334 (10) | 0.0028 (7) | 0.0069 (8) | 0.0004 (7) |
O8 | 0.0134 (9) | 0.0108 (8) | 0.0301 (10) | −0.0025 (7) | 0.0089 (7) | −0.0044 (7) |
N1 | 0.0084 (9) | 0.0086 (8) | 0.0120 (9) | 0.0007 (7) | 0.0034 (7) | 0.0012 (7) |
N2 | 0.0079 (9) | 0.0077 (9) | 0.0155 (9) | −0.0004 (7) | 0.0042 (7) | −0.0005 (7) |
N3 | 0.0159 (10) | 0.0191 (10) | 0.0153 (10) | 0.0024 (8) | 0.0028 (8) | −0.0023 (8) |
C1 | 0.0114 (11) | 0.0081 (10) | 0.0162 (11) | −0.0015 (8) | 0.0036 (9) | 0.0012 (8) |
C2 | 0.0177 (12) | 0.0155 (11) | 0.0209 (12) | 0.0028 (9) | 0.0066 (10) | −0.0034 (9) |
C3 | 0.0256 (14) | 0.0200 (13) | 0.0169 (12) | −0.0017 (10) | 0.0046 (10) | −0.0056 (10) |
C4 | 0.0175 (13) | 0.0232 (13) | 0.0173 (12) | −0.0030 (10) | −0.0025 (10) | −0.0035 (10) |
C5 | 0.0108 (11) | 0.0165 (11) | 0.0201 (12) | −0.0014 (9) | 0.0012 (9) | 0.0001 (9) |
C6 | 0.0120 (11) | 0.0104 (10) | 0.0134 (11) | −0.0015 (8) | 0.0025 (9) | 0.0003 (8) |
C7 | 0.0079 (10) | 0.0105 (10) | 0.0173 (11) | 0.0001 (8) | 0.0033 (8) | 0.0019 (9) |
C8 | 0.0071 (10) | 0.0102 (10) | 0.0153 (11) | 0.0013 (8) | 0.0038 (8) | 0.0002 (8) |
C9 | 0.0105 (11) | 0.0098 (10) | 0.0187 (11) | 0.0011 (8) | 0.0039 (9) | −0.0020 (9) |
C10 | 0.0101 (11) | 0.0105 (10) | 0.0190 (11) | 0.0012 (9) | 0.0067 (9) | −0.0005 (9) |
C11 | 0.0108 (11) | 0.0147 (11) | 0.0164 (11) | −0.0006 (9) | 0.0056 (9) | 0.0001 (9) |
C12 | 0.0126 (11) | 0.0084 (10) | 0.0140 (11) | 0.0010 (8) | 0.0043 (9) | −0.0019 (8) |
C13 | 0.0151 (11) | 0.0146 (11) | 0.0188 (12) | −0.0009 (9) | 0.0060 (9) | 0.0014 (9) |
C14 | 0.0219 (13) | 0.0183 (12) | 0.0188 (12) | 0.0011 (10) | 0.0092 (10) | 0.0061 (10) |
C15 | 0.0165 (12) | 0.0209 (12) | 0.0148 (11) | 0.0059 (10) | −0.0001 (9) | 0.0036 (9) |
C16 | 0.0112 (11) | 0.0139 (11) | 0.0173 (11) | 0.0009 (9) | 0.0018 (9) | −0.0023 (9) |
C17 | 0.0107 (11) | 0.0086 (10) | 0.0148 (11) | 0.0008 (8) | 0.0022 (9) | −0.0014 (8) |
C18 | 0.0081 (10) | 0.0084 (10) | 0.0172 (11) | −0.0003 (8) | 0.0029 (9) | −0.0021 (8) |
C19 | 0.0080 (10) | 0.0110 (10) | 0.0174 (11) | −0.0004 (8) | 0.0051 (9) | 0.0018 (9) |
C20 | 0.0104 (11) | 0.0156 (11) | 0.0174 (11) | 0.0006 (9) | 0.0064 (9) | 0.0029 (9) |
C21 | 0.0116 (11) | 0.0139 (11) | 0.0207 (12) | 0.0010 (9) | 0.0076 (9) | 0.0001 (9) |
C22 | 0.0081 (11) | 0.0111 (11) | 0.0242 (12) | −0.0002 (8) | 0.0066 (9) | 0.0011 (9) |
C23 | 0.0172 (12) | 0.0198 (12) | 0.0222 (13) | 0.0000 (10) | 0.0072 (10) | −0.0027 (10) |
C24 | 0.0314 (15) | 0.0257 (14) | 0.0168 (12) | 0.0075 (12) | 0.0094 (11) | 0.0027 (10) |
C25 | 0.0258 (15) | 0.0317 (15) | 0.0180 (13) | 0.0113 (12) | −0.0034 (11) | −0.0070 (11) |
C26 | 0.0146 (13) | 0.0284 (14) | 0.0328 (15) | 0.0004 (11) | 0.0027 (11) | −0.0113 (12) |
C27 | 0.0224 (13) | 0.0188 (12) | 0.0240 (13) | −0.0006 (10) | 0.0120 (11) | −0.0011 (10) |
Geometric parameters (Å, º) top
Ni1—O1 | 2.004 (2) | C8—C9 | 1.537 (3) |
Ni1—O2 | 2.070 (2) | C8—C11 | 1.539 (3) |
Ni1—O5 | 2.025 (2) | C9—H9A | 0.9900 |
Ni1—O6 | 2.159 (2) | C9—H9B | 0.9900 |
Ni1—N1 | 2.037 (2) | C10—H10A | 0.9900 |
Ni1—N2 | 2.034 (2) | C10—H10B | 0.9900 |
O1—C1 | 1.312 (3) | C11—H11A | 0.9900 |
O2—C9 | 1.426 (3) | C11—H11B | 0.9900 |
O2—H2O | 0.852 (10) | C12—C13 | 1.415 (3) |
O3—C10 | 1.423 (3) | C12—C17 | 1.422 (3) |
O3—H3O | 0.847 (10) | C13—C14 | 1.382 (3) |
O4—C11 | 1.421 (3) | C13—H13 | 0.9500 |
O4—H4O | 0.847 (10) | C14—C15 | 1.392 (4) |
O5—C12 | 1.317 (3) | C14—H14 | 0.9500 |
O6—C20 | 1.438 (3) | C15—C16 | 1.374 (3) |
O6—H6O | 0.843 (10) | C15—H15 | 0.9500 |
O7—C21 | 1.418 (3) | C16—C17 | 1.408 (3) |
O7—H7O | 0.851 (10) | C16—H16 | 0.9500 |
O8—C22 | 1.420 (3) | C17—C18 | 1.450 (3) |
O8—H8O | 0.851 (10) | C18—H18 | 0.9500 |
N1—C7 | 1.281 (3) | C19—C22 | 1.528 (3) |
N1—C8 | 1.479 (3) | C19—C20 | 1.546 (3) |
N2—C18 | 1.284 (3) | C19—C21 | 1.549 (3) |
N2—C19 | 1.480 (3) | C20—H20A | 0.9900 |
N3—C27 | 1.333 (3) | C20—H20B | 0.9900 |
N3—C23 | 1.336 (3) | C21—H21A | 0.9900 |
C1—C2 | 1.418 (3) | C21—H21B | 0.9900 |
C1—C6 | 1.428 (3) | C22—H22A | 0.9900 |
C2—C3 | 1.373 (3) | C22—H22B | 0.9900 |
C2—H2 | 0.9500 | C23—C24 | 1.380 (4) |
C3—C4 | 1.405 (4) | C23—H23 | 0.9500 |
C3—H3 | 0.9500 | C24—C25 | 1.379 (4) |
C4—C5 | 1.367 (3) | C24—H24 | 0.9500 |
C4—H4 | 0.9500 | C25—C26 | 1.376 (4) |
C5—C6 | 1.415 (3) | C25—H25 | 0.9500 |
C5—H5 | 0.9500 | C26—C27 | 1.382 (4) |
C6—C7 | 1.448 (3) | C26—H26 | 0.9500 |
C7—H7 | 0.9500 | C27—H27 | 0.9500 |
C8—C10 | 1.522 (3) | ||
O1—Ni1—O2 | 169.66 (6) | O3—C10—H10B | 109.0 |
O1—Ni1—O5 | 92.51 (6) | C8—C10—H10B | 109.0 |
O1—Ni1—O6 | 90.15 (6) | H10A—C10—H10B | 107.8 |
O1—Ni1—N1 | 91.94 (7) | O4—C11—C8 | 112.43 (18) |
O1—Ni1—N2 | 93.15 (7) | O4—C11—H11A | 109.1 |
O2—Ni1—O5 | 94.49 (7) | C8—C11—H11A | 109.1 |
O2—Ni1—O6 | 84.52 (6) | O4—C11—H11B | 109.1 |
O2—Ni1—N1 | 79.82 (7) | C8—C11—H11B | 109.1 |
O2—Ni1—N2 | 94.50 (7) | H11A—C11—H11B | 107.8 |
O5—Ni1—N1 | 95.61 (7) | O5—C12—C13 | 119.3 (2) |
O5—Ni1—N2 | 89.55 (7) | O5—C12—C17 | 123.4 (2) |
O5—Ni1—O6 | 168.25 (6) | C13—C12—C17 | 117.3 (2) |
O6—Ni1—N1 | 95.74 (7) | C14—C13—C12 | 121.7 (2) |
O6—Ni1—N2 | 78.87 (7) | C14—C13—H13 | 119.1 |
N1—Ni1—N2 | 172.59 (7) | C12—C13—H13 | 119.1 |
C1—O1—Ni1 | 126.58 (14) | C13—C14—C15 | 120.8 (2) |
C9—O2—Ni1 | 114.49 (13) | C13—C14—H14 | 119.6 |
C9—O2—H2O | 111 (2) | C15—C14—H14 | 119.6 |
Ni1—O2—H2O | 126 (2) | C16—C15—C14 | 118.6 (2) |
C10—O3—H3O | 108 (2) | C16—C15—H15 | 120.7 |
C11—O4—H4O | 108 (2) | C14—C15—H15 | 120.7 |
C12—O5—Ni1 | 126.01 (14) | C15—C16—C17 | 122.4 (2) |
C20—O6—Ni1 | 104.88 (12) | C15—C16—H16 | 118.8 |
C20—O6—H6O | 114 (2) | C17—C16—H16 | 118.8 |
Ni1—O6—H6O | 109 (2) | C16—C17—C12 | 119.2 (2) |
C21—O7—H7O | 113 (3) | C16—C17—C18 | 116.3 (2) |
C22—O8—H8O | 105 (2) | C12—C17—C18 | 124.3 (2) |
C7—N1—C8 | 120.47 (19) | N2—C18—C17 | 126.2 (2) |
C7—N1—Ni1 | 124.71 (16) | N2—C18—H18 | 116.9 |
C8—N1—Ni1 | 114.81 (13) | C17—C18—H18 | 116.9 |
C18—N2—C19 | 118.74 (19) | N2—C19—C22 | 114.03 (19) |
C18—N2—Ni1 | 123.78 (16) | N2—C19—C20 | 107.51 (18) |
C19—N2—Ni1 | 116.88 (14) | C22—C19—C20 | 109.60 (19) |
C27—N3—C23 | 118.1 (2) | N2—C19—C21 | 109.68 (18) |
O1—C1—C2 | 119.0 (2) | C22—C19—C21 | 109.54 (18) |
O1—C1—C6 | 124.1 (2) | C20—C19—C21 | 106.16 (18) |
C2—C1—C6 | 117.0 (2) | O6—C20—C19 | 112.53 (18) |
C3—C2—C1 | 122.4 (2) | O6—C20—H20A | 109.1 |
C3—C2—H2 | 118.8 | C19—C20—H20A | 109.1 |
C1—C2—H2 | 118.8 | O6—C20—H20B | 109.1 |
C2—C3—C4 | 120.5 (2) | C19—C20—H20B | 109.1 |
C2—C3—H3 | 119.8 | H20A—C20—H20B | 107.8 |
C4—C3—H3 | 119.8 | O7—C21—C19 | 114.26 (19) |
C5—C4—C3 | 118.6 (2) | O7—C21—H21A | 108.7 |
C5—C4—H4 | 120.7 | C19—C21—H21A | 108.7 |
C3—C4—H4 | 120.7 | O7—C21—H21B | 108.7 |
C4—C5—C6 | 122.6 (2) | C19—C21—H21B | 108.7 |
C4—C5—H5 | 118.7 | H21A—C21—H21B | 107.6 |
C6—C5—H5 | 118.7 | O8—C22—C19 | 110.27 (18) |
C5—C6—C1 | 118.9 (2) | O8—C22—H22A | 109.6 |
C5—C6—C7 | 116.1 (2) | C19—C22—H22A | 109.6 |
C1—C6—C7 | 125.0 (2) | O8—C22—H22B | 109.6 |
N1—C7—C6 | 126.6 (2) | C19—C22—H22B | 109.6 |
N1—C7—H7 | 116.7 | H22A—C22—H22B | 108.1 |
C6—C7—H7 | 116.7 | N3—C23—C24 | 122.8 (2) |
N1—C8—C10 | 115.90 (18) | N3—C23—H23 | 118.6 |
N1—C8—C9 | 106.83 (17) | C24—C23—H23 | 118.6 |
C10—C8—C9 | 109.80 (18) | C25—C24—C23 | 118.6 (3) |
N1—C8—C11 | 108.37 (17) | C25—C24—H24 | 120.7 |
C10—C8—C11 | 106.50 (18) | C23—C24—H24 | 120.7 |
C9—C8—C11 | 109.33 (18) | C26—C25—C24 | 118.9 (2) |
O2—C9—C8 | 110.23 (17) | C26—C25—H25 | 120.6 |
O2—C9—H9A | 109.6 | C24—C25—H25 | 120.6 |
C8—C9—H9A | 109.6 | C25—C26—C27 | 119.0 (2) |
O2—C9—H9B | 109.6 | C25—C26—H26 | 120.5 |
C8—C9—H9B | 109.6 | C27—C26—H26 | 120.5 |
H9A—C9—H9B | 108.1 | N3—C27—C26 | 122.5 (2) |
O3—C10—C8 | 112.85 (18) | N3—C27—H27 | 118.7 |
O3—C10—H10A | 109.0 | C26—C27—H27 | 118.7 |
C8—C10—H10A | 109.0 | ||
O5—Ni1—O1—C1 | −107.67 (17) | Ni1—N1—C8—C10 | −156.16 (15) |
N2—Ni1—O1—C1 | 162.64 (18) | C7—N1—C8—C9 | 147.6 (2) |
N1—Ni1—O1—C1 | −11.97 (18) | Ni1—N1—C8—C9 | −33.5 (2) |
O2—Ni1—O1—C1 | 25.0 (5) | C7—N1—C8—C11 | −94.7 (2) |
O6—Ni1—O1—C1 | 83.78 (17) | Ni1—N1—C8—C11 | 84.24 (18) |
O1—Ni1—O2—C9 | −28.1 (4) | Ni1—O2—C9—C8 | −30.3 (2) |
O5—Ni1—O2—C9 | 104.39 (14) | N1—C8—C9—O2 | 40.2 (2) |
N2—Ni1—O2—C9 | −165.71 (15) | C10—C8—C9—O2 | 166.60 (18) |
N1—Ni1—O2—C9 | 9.48 (14) | C11—C8—C9—O2 | −76.9 (2) |
O6—Ni1—O2—C9 | −87.37 (14) | N1—C8—C10—O3 | 54.1 (3) |
O1—Ni1—O5—C12 | −118.02 (17) | C9—C8—C10—O3 | −67.0 (2) |
N2—Ni1—O5—C12 | −24.88 (18) | C11—C8—C10—O3 | 174.68 (18) |
N1—Ni1—O5—C12 | 149.79 (17) | N1—C8—C11—O4 | 62.1 (2) |
O2—Ni1—O5—C12 | 69.60 (18) | C10—C8—C11—O4 | −63.2 (2) |
O6—Ni1—O5—C12 | −15.1 (4) | C9—C8—C11—O4 | 178.23 (17) |
O1—Ni1—O6—C20 | 57.73 (13) | Ni1—O5—C12—C13 | −167.18 (15) |
O5—Ni1—O6—C20 | −45.4 (4) | Ni1—O5—C12—C17 | 13.9 (3) |
N2—Ni1—O6—C20 | −35.46 (13) | O5—C12—C13—C14 | 178.8 (2) |
N1—Ni1—O6—C20 | 149.69 (13) | C17—C12—C13—C14 | −2.2 (3) |
O2—Ni1—O6—C20 | −131.15 (13) | C12—C13—C14—C15 | 0.7 (4) |
O1—Ni1—N1—C7 | 7.21 (19) | C13—C14—C15—C16 | 0.8 (4) |
O5—Ni1—N1—C7 | 99.93 (18) | C14—C15—C16—C17 | −0.7 (4) |
O2—Ni1—N1—C7 | −166.50 (19) | C15—C16—C17—C12 | −0.8 (3) |
O6—Ni1—N1—C7 | −83.13 (19) | C15—C16—C17—C18 | 174.6 (2) |
O1—Ni1—N1—C8 | −171.67 (14) | O5—C12—C17—C16 | −178.8 (2) |
O5—Ni1—N1—C8 | −78.95 (15) | C13—C12—C17—C16 | 2.3 (3) |
O2—Ni1—N1—C8 | 14.62 (14) | O5—C12—C17—C18 | 6.1 (3) |
O6—Ni1—N1—C8 | 97.98 (14) | C13—C12—C17—C18 | −172.8 (2) |
O1—Ni1—N2—C18 | 118.25 (18) | C19—N2—C18—C17 | 172.4 (2) |
O5—Ni1—N2—C18 | 25.75 (18) | Ni1—N2—C18—C17 | −16.8 (3) |
O2—Ni1—N2—C18 | −68.72 (18) | C16—C17—C18—N2 | −179.6 (2) |
O6—Ni1—N2—C18 | −152.22 (18) | C12—C17—C18—N2 | −4.4 (4) |
O1—Ni1—N2—C19 | −70.78 (15) | C18—N2—C19—C22 | 51.1 (3) |
O5—Ni1—N2—C19 | −163.28 (15) | Ni1—N2—C19—C22 | −120.30 (17) |
O2—Ni1—N2—C19 | 102.25 (15) | C18—N2—C19—C20 | 172.87 (19) |
O6—Ni1—N2—C19 | 18.75 (15) | Ni1—N2—C19—C20 | 1.4 (2) |
Ni1—O1—C1—C2 | −169.19 (16) | C18—N2—C19—C21 | −72.1 (2) |
Ni1—O1—C1—C6 | 11.1 (3) | Ni1—N2—C19—C21 | 116.44 (16) |
O1—C1—C2—C3 | 180.0 (2) | Ni1—O6—C20—C19 | 47.5 (2) |
C6—C1—C2—C3 | −0.4 (3) | N2—C19—C20—O6 | −33.8 (2) |
C1—C2—C3—C4 | 0.7 (4) | C22—C19—C20—O6 | 90.7 (2) |
C2—C3—C4—C5 | −0.6 (4) | C21—C19—C20—O6 | −151.12 (18) |
C3—C4—C5—C6 | 0.3 (4) | N2—C19—C21—O7 | 55.7 (2) |
C4—C5—C6—C1 | 0.0 (4) | C22—C19—C21—O7 | −70.2 (2) |
C4—C5—C6—C7 | −178.5 (2) | C20—C19—C21—O7 | 171.55 (18) |
O1—C1—C6—C5 | 179.7 (2) | N2—C19—C22—O8 | 61.5 (2) |
C2—C1—C6—C5 | 0.0 (3) | C20—C19—C22—O8 | −59.1 (2) |
O1—C1—C6—C7 | −1.9 (4) | C21—C19—C22—O8 | −175.18 (18) |
C2—C1—C6—C7 | 178.4 (2) | C27—N3—C23—C24 | −0.4 (4) |
C8—N1—C7—C6 | 177.2 (2) | N3—C23—C24—C25 | −0.2 (4) |
Ni1—N1—C7—C6 | −1.6 (3) | C23—C24—C25—C26 | 0.8 (4) |
C5—C6—C7—N1 | 175.3 (2) | C24—C25—C26—C27 | −0.7 (4) |
C1—C6—C7—N1 | −3.2 (4) | C23—N3—C27—C26 | 0.5 (4) |
C7—N1—C8—C10 | 24.9 (3) | C25—C26—C27—N3 | 0.1 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2o···N3 | 0.85 (1) | 1.76 (1) | 2.599 (2) | 169 (3) |
O3—H3o···O5i | 0.85 (1) | 1.75 (1) | 2.593 (2) | 177 (3) |
O4—H4o···O3ii | 0.85 (1) | 1.82 (1) | 2.651 (2) | 169 (3) |
O6—H6o···O7iii | 0.84 (1) | 2.12 (2) | 2.868 (2) | 148 (3) |
O7—H7o···O4iv | 0.85 (1) | 1.90 (1) | 2.734 (2) | 166 (4) |
O8—H8o···O1iii | 0.85 (1) | 1.88 (1) | 2.728 (2) | 174 (3) |
Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) −x+3/2, y+1/2, −z+3/2; (iii) −x+1/2, y−1/2, −z+3/2; (iv) x−1, y, z. |