Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680301585X/lh6086sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680301585X/lh6086Isup2.hkl |
CCDC reference: 222796
To a solution of Ni(O2CC5H5)2·4H2O (0.5 mmol) and benzoic acid (1 mmol) in ethanol (25 ml) was added a solid sample of PPN (1 mmol). The solution was stirred for 30 min, after which a small quantity of green solid precipitated. After filtration, the clear solution, kept in the dark, was slowly evaporated at room temperature over a period of one month, yielding green crystals suitable for analysis.
The C—H atoms were included in the riding-model approximation, with C—H distances of 0.94 Å (0.97 Å for methyl), Uiso(phenyl-H) = 1.2Ueq(C) and Uiso(methyl-H) = 1.5Ueq(C). The water H atoms were located from a difference map and refined, subject to O—H 0.85±0.01 Å, H···H 1.39±0.01 Å and Uiso(H) = 1.5Ueq(O).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SHELXTL (Bruker, 2000); program(s) used to solve structure: PATTY in DIRDIF92 (Beurskens et al., 1992); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHEXLTL.
[Ni(C7H5O2)2(C12H16N3O2)2(H2O)2] | Z = 1 |
Mr = 805.52 | F(000) = 424 |
Triclinic, P1 | Dx = 1.395 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71069 Å |
a = 6.7001 (3) Å | Cell parameters from 2446 reflections |
b = 11.3354 (6) Å | θ = 2.4–28.9° |
c = 12.8740 (6) Å | µ = 0.57 mm−1 |
α = 86.319 (2)° | T = 223 K |
β = 87.290 (2)° | Irregular block, green |
γ = 79.486 (2)° | 0.28 × 0.14 × 0.10 mm |
V = 958.73 (8) Å3 |
Bruker AXS SMART CCD diffractometer | 5468 independent reflections |
Radiation source: fine-focus sealed tube | 4462 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
ω scans | θmax = 30.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2000; Blessing, 1995) | h = −8→9 |
Tmin = 0.725, Tmax = 0.944 | k = −15→14 |
8055 measured reflections | l = −16→18 |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0644P)2] where P = (Fo2 + 2Fc2)/3 |
5468 reflections | (Δ/σ)max < 0.001 |
256 parameters | Δρmax = 0.61 e Å−3 |
3 restraints | Δρmin = −0.25 e Å−3 |
[Ni(C7H5O2)2(C12H16N3O2)2(H2O)2] | γ = 79.486 (2)° |
Mr = 805.52 | V = 958.73 (8) Å3 |
Triclinic, P1 | Z = 1 |
a = 6.7001 (3) Å | Mo Kα radiation |
b = 11.3354 (6) Å | µ = 0.57 mm−1 |
c = 12.8740 (6) Å | T = 223 K |
α = 86.319 (2)° | 0.28 × 0.14 × 0.10 mm |
β = 87.290 (2)° |
Bruker AXS SMART CCD diffractometer | 5468 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000; Blessing, 1995) | 4462 reflections with I > 2σ(I) |
Tmin = 0.725, Tmax = 0.944 | Rint = 0.022 |
8055 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 3 restraints |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.61 e Å−3 |
5468 reflections | Δρmin = −0.25 e Å−3 |
256 parameters |
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 | ||
Ni | 0.0000 | 0.0000 | 0.0000 | 0.02173 (10) | |
O1 | −0.01610 (18) | −0.16791 (11) | −0.04550 (10) | 0.0278 (3) | |
O2 | −0.3471 (2) | −0.17010 (13) | −0.02102 (13) | 0.0405 (4) | |
O3 | 0.6300 (2) | −0.38082 (13) | 0.36734 (12) | 0.0432 (4) | |
O4 | 0.2517 (2) | −0.06243 (13) | 0.53705 (11) | 0.0396 (4) | |
O5 | 0.28606 (18) | −0.01457 (12) | −0.07767 (10) | 0.0281 (3) | |
H5A | 0.380 (3) | −0.0741 (12) | −0.0744 (18) | 0.041* | |
H5B | 0.318 (3) | 0.0442 (13) | −0.0495 (18) | 0.041* | |
N1 | 0.1245 (2) | −0.07638 (13) | 0.14092 (12) | 0.0242 (3) | |
N2 | 0.5626 (2) | −0.30567 (14) | 0.43553 (12) | 0.0280 (3) | |
N3 | 0.3782 (2) | −0.15731 (14) | 0.51694 (12) | 0.0262 (3) | |
C1 | −0.1699 (3) | −0.21662 (16) | −0.04950 (14) | 0.0260 (4) | |
C2 | −0.1390 (3) | −0.33964 (16) | −0.09127 (14) | 0.0263 (4) | |
C3 | 0.0508 (3) | −0.39467 (18) | −0.12632 (16) | 0.0333 (4) | |
H3 | 0.1616 | −0.3547 | −0.1241 | 0.040* | |
C4 | 0.0800 (4) | −0.5083 (2) | −0.16472 (18) | 0.0416 (5) | |
H4 | 0.2094 | −0.5442 | −0.1897 | 0.050* | |
C5 | −0.0810 (4) | −0.5687 (2) | −0.16633 (19) | 0.0439 (5) | |
H5 | −0.0612 | −0.6460 | −0.1918 | 0.053* | |
C6 | −0.2715 (4) | −0.5149 (2) | −0.13041 (19) | 0.0431 (5) | |
H6 | −0.3812 | −0.5560 | −0.1312 | 0.052* | |
C7 | −0.3014 (3) | −0.40071 (19) | −0.09323 (17) | 0.0357 (4) | |
H7 | −0.4314 | −0.3644 | −0.0693 | 0.043* | |
C8 | 0.2922 (3) | −0.16078 (17) | 0.14235 (15) | 0.0287 (4) | |
H8 | 0.3470 | −0.1907 | 0.0787 | 0.034* | |
C9 | 0.3890 (3) | −0.20618 (17) | 0.23221 (15) | 0.0289 (4) | |
H9 | 0.5087 | −0.2641 | 0.2288 | 0.035* | |
C10 | 0.3092 (3) | −0.16600 (15) | 0.32811 (14) | 0.0231 (3) | |
C11 | 0.1299 (3) | −0.08011 (17) | 0.32730 (14) | 0.0269 (4) | |
H11 | 0.0676 | −0.0514 | 0.3900 | 0.032* | |
C12 | 0.0463 (3) | −0.03839 (17) | 0.23302 (14) | 0.0277 (4) | |
H12 | −0.0727 | 0.0202 | 0.2335 | 0.033* | |
C13 | 0.4110 (3) | −0.20883 (16) | 0.42441 (14) | 0.0247 (4) | |
C14 | 0.6664 (3) | −0.30747 (17) | 0.53683 (15) | 0.0292 (4) | |
C15 | 0.4976 (3) | −0.23102 (17) | 0.60175 (15) | 0.0291 (4) | |
C16 | 0.8510 (3) | −0.2476 (2) | 0.5093 (2) | 0.0472 (6) | |
H16A | 0.8054 | −0.1655 | 0.4830 | 0.071* | |
H16B | 0.9359 | −0.2917 | 0.4565 | 0.071* | |
H16C | 0.9284 | −0.2478 | 0.5711 | 0.071* | |
C17 | 0.7337 (3) | −0.43630 (19) | 0.57829 (18) | 0.0421 (5) | |
H17A | 0.6152 | −0.4728 | 0.5953 | 0.063* | |
H17B | 0.8106 | −0.4372 | 0.6404 | 0.063* | |
H17C | 0.8182 | −0.4812 | 0.5257 | 0.063* | |
C18 | 0.5709 (4) | −0.1479 (2) | 0.67438 (18) | 0.0449 (5) | |
H18A | 0.6627 | −0.1026 | 0.6360 | 0.067* | |
H18B | 0.6413 | −0.1955 | 0.7314 | 0.067* | |
H18C | 0.4552 | −0.0929 | 0.7019 | 0.067* | |
C19 | 0.3535 (3) | −0.3029 (2) | 0.66032 (17) | 0.0393 (5) | |
H19A | 0.3081 | −0.3553 | 0.6133 | 0.059* | |
H19B | 0.2371 | −0.2484 | 0.6878 | 0.059* | |
H19C | 0.4232 | −0.3510 | 0.7173 | 0.059* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni | 0.01822 (16) | 0.02606 (18) | 0.02039 (16) | −0.00221 (12) | −0.00125 (11) | −0.00219 (12) |
O1 | 0.0225 (6) | 0.0292 (7) | 0.0316 (7) | −0.0034 (5) | −0.0001 (5) | −0.0056 (5) |
O2 | 0.0226 (6) | 0.0387 (8) | 0.0605 (10) | −0.0031 (6) | 0.0019 (7) | −0.0153 (7) |
O3 | 0.0507 (9) | 0.0355 (8) | 0.0352 (8) | 0.0153 (7) | 0.0005 (7) | −0.0066 (6) |
O4 | 0.0430 (8) | 0.0371 (8) | 0.0314 (7) | 0.0160 (6) | −0.0054 (6) | −0.0106 (6) |
O5 | 0.0211 (6) | 0.0333 (7) | 0.0292 (7) | −0.0021 (5) | −0.0012 (5) | −0.0036 (6) |
N1 | 0.0215 (7) | 0.0274 (7) | 0.0236 (7) | −0.0035 (6) | −0.0019 (6) | −0.0027 (6) |
N2 | 0.0260 (7) | 0.0270 (8) | 0.0273 (8) | 0.0040 (6) | −0.0002 (6) | 0.0011 (6) |
N3 | 0.0253 (7) | 0.0265 (8) | 0.0245 (7) | 0.0020 (6) | −0.0038 (6) | −0.0011 (6) |
C1 | 0.0253 (8) | 0.0286 (9) | 0.0234 (8) | −0.0025 (7) | −0.0041 (7) | −0.0005 (7) |
C2 | 0.0299 (9) | 0.0265 (9) | 0.0228 (8) | −0.0050 (7) | −0.0045 (7) | 0.0002 (7) |
C3 | 0.0332 (10) | 0.0336 (10) | 0.0331 (10) | −0.0062 (8) | 0.0018 (8) | −0.0025 (8) |
C4 | 0.0429 (12) | 0.0358 (11) | 0.0433 (12) | 0.0010 (9) | 0.0034 (10) | −0.0080 (9) |
C5 | 0.0613 (14) | 0.0294 (10) | 0.0419 (12) | −0.0076 (10) | −0.0078 (11) | −0.0064 (9) |
C6 | 0.0490 (13) | 0.0383 (12) | 0.0466 (13) | −0.0174 (10) | −0.0089 (11) | −0.0043 (10) |
C7 | 0.0328 (10) | 0.0369 (11) | 0.0387 (11) | −0.0092 (8) | −0.0039 (9) | −0.0024 (9) |
C8 | 0.0308 (9) | 0.0304 (9) | 0.0226 (9) | 0.0002 (7) | 0.0028 (7) | −0.0028 (7) |
C9 | 0.0267 (9) | 0.0288 (9) | 0.0271 (9) | 0.0062 (7) | −0.0006 (7) | −0.0018 (7) |
C10 | 0.0217 (8) | 0.0229 (8) | 0.0239 (8) | −0.0027 (6) | −0.0011 (6) | −0.0002 (6) |
C11 | 0.0233 (8) | 0.0318 (9) | 0.0238 (9) | 0.0011 (7) | 0.0003 (7) | −0.0049 (7) |
C12 | 0.0213 (8) | 0.0323 (10) | 0.0269 (9) | 0.0036 (7) | −0.0029 (7) | −0.0040 (7) |
C13 | 0.0232 (8) | 0.0242 (8) | 0.0248 (8) | 0.0005 (7) | −0.0001 (7) | −0.0006 (7) |
C14 | 0.0225 (8) | 0.0318 (10) | 0.0316 (10) | −0.0013 (7) | −0.0045 (7) | 0.0039 (8) |
C15 | 0.0281 (9) | 0.0319 (10) | 0.0261 (9) | −0.0019 (7) | −0.0071 (7) | 0.0019 (7) |
C16 | 0.0252 (10) | 0.0538 (14) | 0.0618 (16) | −0.0081 (9) | −0.0010 (10) | 0.0055 (12) |
C17 | 0.0398 (11) | 0.0380 (12) | 0.0421 (12) | 0.0070 (9) | −0.0078 (10) | 0.0103 (9) |
C18 | 0.0480 (13) | 0.0478 (13) | 0.0395 (12) | −0.0047 (10) | −0.0185 (10) | −0.0071 (10) |
C19 | 0.0343 (10) | 0.0476 (12) | 0.0322 (11) | −0.0022 (9) | 0.0017 (8) | 0.0090 (9) |
Ni—O1 | 2.0497 (13) | C6—H6 | 0.9400 |
Ni—O5 | 2.1036 (13) | C7—H7 | 0.9400 |
Ni—N1 | 2.1011 (15) | C8—C9 | 1.377 (3) |
Ni—O1i | 2.0497 (13) | C8—H8 | 0.9400 |
Ni—N1i | 2.1011 (15) | C9—C10 | 1.393 (3) |
Ni—O5i | 2.1036 (13) | C9—H9 | 0.9400 |
O1—C1 | 1.260 (2) | C10—C11 | 1.401 (2) |
O2—C1 | 1.256 (2) | C10—C13 | 1.456 (2) |
O3—N2 | 1.272 (2) | C11—C12 | 1.380 (2) |
O4—N3 | 1.274 (2) | C11—H11 | 0.9400 |
O5—H5A | 0.836 (9) | C12—H12 | 0.9400 |
O5—H5B | 0.844 (9) | C14—C17 | 1.518 (3) |
N1—C8 | 1.336 (2) | C14—C16 | 1.532 (3) |
N1—C12 | 1.338 (2) | C14—C15 | 1.541 (3) |
N2—C13 | 1.358 (2) | C15—C19 | 1.518 (3) |
N2—C14 | 1.504 (2) | C15—C18 | 1.526 (3) |
N3—C13 | 1.351 (2) | C16—H16A | 0.9700 |
N3—C15 | 1.501 (2) | C16—H16B | 0.9700 |
C1—C2 | 1.502 (3) | C16—H16C | 0.9700 |
C2—C3 | 1.379 (3) | C17—H17A | 0.9700 |
C2—C7 | 1.394 (3) | C17—H17B | 0.9700 |
C3—C4 | 1.386 (3) | C17—H17C | 0.9700 |
C3—H3 | 0.9400 | C18—H18A | 0.9700 |
C4—C5 | 1.381 (3) | C18—H18B | 0.9700 |
C4—H4 | 0.9400 | C18—H18C | 0.9700 |
C5—C6 | 1.382 (3) | C19—H19A | 0.9700 |
C5—H5 | 0.9400 | C19—H19B | 0.9700 |
C6—C7 | 1.386 (3) | C19—H19C | 0.9700 |
O1—Ni—O5 | 88.52 (5) | C8—C9—C10 | 119.78 (16) |
O1—Ni—N1 | 89.99 (5) | C8—C9—H9 | 120.1 |
O1—Ni—O5i | 91.48 (5) | C10—C9—H9 | 120.1 |
O1—Ni—N1i | 90.01 (5) | C9—C10—C11 | 116.99 (16) |
O5—Ni—N1 | 93.10 (5) | C9—C10—C13 | 121.35 (15) |
O5—Ni—N1i | 86.90 (5) | C11—C10—C13 | 121.64 (16) |
O1i—Ni—O1 | 180.00 (7) | C12—C11—C10 | 118.94 (17) |
O1i—Ni—N1 | 90.01 (5) | C12—C11—H11 | 120.5 |
O1i—Ni—N1i | 89.99 (5) | C10—C11—H11 | 120.5 |
N1—Ni—N1i | 180.00 (9) | N1—C12—C11 | 123.89 (16) |
O1i—Ni—O5i | 88.52 (5) | N1—C12—H12 | 118.1 |
N1—Ni—O5i | 86.90 (5) | C11—C12—H12 | 118.1 |
N1i—Ni—O5i | 93.10 (5) | N3—C13—N2 | 107.91 (15) |
O1i—Ni—O5 | 91.48 (5) | N3—C13—C10 | 126.50 (15) |
O5i—Ni—O5 | 180.00 (10) | N2—C13—C10 | 125.53 (16) |
C1—O1—Ni | 128.78 (12) | N2—C14—C17 | 109.83 (16) |
Ni—O5—H5A | 126.3 (17) | N2—C14—C16 | 104.79 (17) |
Ni—O5—H5B | 94.6 (16) | C17—C14—C16 | 110.55 (16) |
H5A—O5—H5B | 110.8 (14) | N2—C14—C15 | 100.65 (13) |
C8—N1—C12 | 116.91 (15) | C17—C14—C15 | 115.74 (17) |
C8—N1—Ni | 121.35 (12) | C16—C14—C15 | 114.17 (18) |
C12—N1—Ni | 121.65 (12) | N3—C15—C19 | 106.35 (15) |
O3—N2—C13 | 126.79 (16) | N3—C15—C18 | 109.55 (16) |
O3—N2—C14 | 121.32 (14) | C19—C15—C18 | 110.31 (18) |
C13—N2—C14 | 111.48 (15) | N3—C15—C14 | 100.68 (14) |
O4—N3—C13 | 126.77 (15) | C19—C15—C14 | 114.00 (17) |
O4—N3—C15 | 120.83 (15) | C18—C15—C14 | 115.09 (17) |
C13—N3—C15 | 112.21 (14) | C14—C16—H16A | 109.5 |
O2—C1—O1 | 124.87 (17) | C14—C16—H16B | 109.5 |
O2—C1—C2 | 117.59 (16) | H16A—C16—H16B | 109.5 |
O1—C1—C2 | 117.53 (16) | C14—C16—H16C | 109.5 |
C3—C2—C7 | 119.08 (18) | H16A—C16—H16C | 109.5 |
C3—C2—C1 | 120.58 (17) | H16B—C16—H16C | 109.5 |
C7—C2—C1 | 120.33 (17) | C14—C17—H17A | 109.5 |
C2—C3—C4 | 120.7 (2) | C14—C17—H17B | 109.5 |
C2—C3—H3 | 119.6 | H17A—C17—H17B | 109.5 |
C4—C3—H3 | 119.6 | C14—C17—H17C | 109.5 |
C5—C4—C3 | 120.1 (2) | H17A—C17—H17C | 109.5 |
C5—C4—H4 | 120.0 | H17B—C17—H17C | 109.5 |
C3—C4—H4 | 120.0 | C15—C18—H18A | 109.5 |
C4—C5—C6 | 119.7 (2) | C15—C18—H18B | 109.5 |
C4—C5—H5 | 120.1 | H18A—C18—H18B | 109.5 |
C6—C5—H5 | 120.1 | C15—C18—H18C | 109.5 |
C5—C6—C7 | 120.3 (2) | H18A—C18—H18C | 109.5 |
C5—C6—H6 | 119.9 | H18B—C18—H18C | 109.5 |
C7—C6—H6 | 119.9 | C15—C19—H19A | 109.5 |
C6—C7—C2 | 120.1 (2) | C15—C19—H19B | 109.5 |
C6—C7—H7 | 119.9 | H19A—C19—H19B | 109.5 |
C2—C7—H7 | 119.9 | C15—C19—H19C | 109.5 |
N1—C8—C9 | 123.44 (17) | H19A—C19—H19C | 109.5 |
N1—C8—H8 | 118.3 | H19B—C19—H19C | 109.5 |
C9—C8—H8 | 118.3 |
Symmetry code: (i) −x, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | [Ni(C7H5O2)2(C12H16N3O2)2(H2O)2] |
Mr | 805.52 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 223 |
a, b, c (Å) | 6.7001 (3), 11.3354 (6), 12.8740 (6) |
α, β, γ (°) | 86.319 (2), 87.290 (2), 79.486 (2) |
V (Å3) | 958.73 (8) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.57 |
Crystal size (mm) | 0.28 × 0.14 × 0.10 |
Data collection | |
Diffractometer | Bruker AXS SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2000; Blessing, 1995) |
Tmin, Tmax | 0.725, 0.944 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8055, 5468, 4462 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.704 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.123, 1.05 |
No. of reflections | 5468 |
No. of parameters | 256 |
No. of restraints | 3 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.61, −0.25 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Bruker, 2000), PATTY in DIRDIF92 (Beurskens et al., 1992), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHEXLTL.
Ni—O1 | 2.0497 (13) | O2—C1 | 1.256 (2) |
Ni—O5 | 2.1036 (13) | O3—N2 | 1.272 (2) |
Ni—N1 | 2.1011 (15) | O4—N3 | 1.274 (2) |
O1—C1 | 1.260 (2) | ||
O1—Ni—O5 | 88.52 (5) | O1—Ni—N1i | 90.01 (5) |
O1—Ni—N1 | 89.99 (5) | O5—Ni—N1 | 93.10 (5) |
O1—Ni—O5i | 91.48 (5) | O5—Ni—N1i | 86.90 (5) |
Symmetry code: (i) −x, −y, −z. |
The title compound, (I), is isomorphous with the MnII species that was investigated for novel magnetic characterisitics owing to the presence of the radical ligand, PPN, i.e. 2-(p-pyridyl)-4,4,5,5-tetramethylimidazoline-1-oxyl 3-oxide (Fettouhi et al., 1999). The Ni atom is situated on a centre of inversion and exists in a distorted octahedral geometry defined by an all trans-N2O4 donor set (Fig. 1 and Table 1). The benzoate ligand is effectively mondentate as the Ni···O2 distance is 3.3110 (14) Å. There are both intra- and intermolecular hydrogen-bonding interactions involving the coordinated water molecules and the O2 atoms. The parameters associated with the intramolecular interaction are H···O2 = 1.78 Å, O2···O5 = 2.620 (2) Å and angle at H = 171°. The intermolecular interactions occur between translationally related molecules, along the a direction, and are characterized by H···O2i = 2.07 Å, O5···O2i = 2.8468 (19) Å and the angle at H = 154 [symmetry code: (i) 1 + x, y, z]. These interactions lead to the formation of 12-membered [–Ni—O—H···O—C—O–]2 rings and the chains that are thereby formed are separated by regions occupied by the PPN ligands (Fig. 2). Links between the chains are facilitated by C11—H···O4ii contacts so that H···O4ii = 2.47 Å, C11···O4ii = 3.260 (2) Å and the angle subtended at H being 142° [symmetry code: (ii) −x, −y, 1 − z]. Links between the PPN ligands also occur via C—H···O interactions so that C17—H···O3iii = 2.55 Å, C17····O3iii = 3.496 (3) Å and the angle at H = 165° and C16—H···O4iv = 2.54 Å, C16···O4iv = 3.474 (3) Å and the angle at H = 162° [symmetry codes: (iii) 1 − x, −1 − y, 1 − z; (iv) 1 − x, −y, 1 − z].