metal-organic compounds
In the title complex {systematic name: aqua[p-phenylenebis(dioxyacetato)-κO]tetrakis(1H-imidazole-κN3)nickel(II) monohydrate}, [Ni(C10H8O6)(C3H4N2)4(H2O)]·H2O, the NiII atom shows a distorted octahedral configuration, defined by one carboxyl O atom of the benzene-1,3-dioxyacetate group, four N atoms from four imidazole ligands and one water molecule. A three-dimensional supramolecular network is constructed by hydrogen-bonding and π–π stacking interactions.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804027709/er6004sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804027709/er6004Isup2.hkl |
CCDC reference: 258631
Computing details top
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Crystal data top
[Ni(C10H8O6)(C3H4N2)4(H2O)]·H2O | Z = 2 |
Mr = 591.21 | F(000) = 616 |
Triclinic, P1 | Dx = 1.494 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.3099 (17) Å | Cell parameters from 12270 reflections |
b = 9.896 (2) Å | θ = 3.2–27.5° |
c = 16.986 (3) Å | µ = 0.80 mm−1 |
α = 75.95 (3)° | T = 293 K |
β = 75.93 (3)° | Prism, green |
γ = 87.62 (3)° | 0.38 × 0.27 × 0.19 mm |
V = 1314.2 (5) Å3 |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 5980 independent reflections |
Radiation source: fine-focus sealed tube | 4469 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
Detector resolution: 10 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −12→12 |
Tmin = 0.751, Tmax = 0.863 | l = −22→21 |
12870 measured reflections |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.112 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0575P)2 + 0.4263P] where P = (Fo2 + 2Fc2)/3 |
5980 reflections | (Δ/σ)max = 0.001 |
364 parameters | Δρmax = 0.60 e Å−3 |
6 restraints | Δρmin = −0.32 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Ni1 | 0.59626 (4) | 0.59054 (4) | 0.218253 (18) | 0.0287 (1) | |
N1 | 0.4526 (3) | 0.7454 (2) | 0.16209 (13) | 0.0373 (5) | |
N2 | 0.2720 (3) | 0.9163 (3) | 0.15821 (17) | 0.0511 (6) | |
N3 | 0.8003 (3) | 0.6357 (2) | 0.11502 (13) | 0.0361 (5) | |
N4 | 0.9456 (3) | 0.6640 (3) | −0.01503 (14) | 0.0471 (6) | |
N5 | 0.5243 (3) | 0.4307 (2) | 0.17245 (13) | 0.0358 (5) | |
N6 | 0.5322 (3) | 0.2232 (3) | 0.14655 (15) | 0.0444 (6) | |
N7 | 0.3959 (3) | 0.5335 (2) | 0.32312 (12) | 0.0331 (5) | |
N8 | 0.2507 (3) | 0.4467 (2) | 0.45168 (13) | 0.0388 (5) | |
O1 | 0.6737 (2) | 0.7510 (2) | 0.26680 (10) | 0.0365 (4) | |
O2 | 0.7643 (2) | 0.6333 (2) | 0.37733 (11) | 0.0406 (5) | |
O3 | 0.7282 (3) | 0.8444 (2) | 0.44665 (11) | 0.0493 (5) | |
O4 | 0.8743 (3) | 0.9737 (2) | 0.67201 (11) | 0.0420 (5) | |
O5 | 0.9852 (3) | 0.9095 (2) | 0.81121 (12) | 0.0446 (5) | |
O6 | 1.0163 (2) | 0.6874 (2) | 0.80822 (11) | 0.0402 (4) | |
O1W | 0.7461 (2) | 0.4500 (2) | 0.28594 (11) | 0.0369 (4) | |
O2W | 0.7404 (3) | 1.0025 (2) | 0.13848 (16) | 0.0569 (6) | |
C1 | 0.3517 (4) | 0.8261 (3) | 0.20569 (19) | 0.0496 (7) | |
C2 | 0.3236 (5) | 0.8980 (4) | 0.0782 (2) | 0.0620 (9) | |
C3 | 0.4340 (4) | 0.7925 (4) | 0.08350 (19) | 0.0561 (9) | |
C4 | 0.8085 (4) | 0.6116 (3) | 0.04066 (16) | 0.0394 (6) | |
C5 | 1.0350 (5) | 0.7233 (4) | 0.0252 (2) | 0.0658 (10) | |
C6 | 0.9448 (4) | 0.7042 (4) | 0.1050 (2) | 0.0574 (9) | |
C7 | 0.5994 (4) | 0.3112 (4) | 0.1782 (2) | 0.0521 (8) | |
C8 | 0.4014 (4) | 0.2890 (3) | 0.11986 (18) | 0.0445 (7) | |
C9 | 0.3984 (4) | 0.4162 (3) | 0.13546 (18) | 0.0433 (7) | |
C10 | 0.4001 (3) | 0.4839 (3) | 0.40183 (16) | 0.0386 (6) | |
C11 | 0.1396 (4) | 0.4725 (3) | 0.40270 (17) | 0.0418 (6) | |
C12 | 0.2293 (3) | 0.5261 (3) | 0.32388 (16) | 0.0394 (6) | |
C13 | 0.7148 (3) | 0.7415 (3) | 0.33531 (15) | 0.0316 (5) | |
C14 | 0.7020 (4) | 0.8748 (3) | 0.36465 (15) | 0.0378 (6) | |
C15 | 0.7425 (3) | 0.9517 (3) | 0.48274 (15) | 0.0346 (6) | |
C16 | 0.7107 (4) | 1.0887 (3) | 0.45203 (16) | 0.0386 (6) | |
C17 | 0.7368 (4) | 1.1854 (3) | 0.49523 (17) | 0.0421 (7) | |
C18 | 0.7923 (4) | 1.1466 (3) | 0.56780 (16) | 0.0405 (6) | |
C19 | 0.8196 (3) | 1.0065 (3) | 0.59923 (15) | 0.0349 (6) | |
C20 | 0.7937 (4) | 0.9090 (3) | 0.55745 (15) | 0.0365 (6) | |
C21 | 0.9106 (3) | 0.8310 (3) | 0.70149 (15) | 0.0344 (6) | |
C22 | 0.9761 (3) | 0.8099 (3) | 0.77990 (15) | 0.0322 (6) | |
H1 | 0.3397 | 0.8190 | 0.2624 | 0.059* | |
H2 | 0.2904 | 0.9470 | 0.0309 | 0.074* | |
H3 | 0.4896 | 0.7573 | 0.0384 | 0.067* | |
H4 | 0.7270 | 0.5633 | 0.0290 | 0.047* | |
H5 | 1.1379 | 0.7682 | 0.0024 | 0.079* | |
H6 | 0.9771 | 0.7337 | 0.1470 | 0.069* | |
H7 | 0.6900 | 0.2900 | 0.2018 | 0.062* | |
H8 | 0.3288 | 0.2533 | 0.0957 | 0.053* | |
H9 | 0.3219 | 0.4845 | 0.1230 | 0.052* | |
H10 | 0.4971 | 0.4757 | 0.4206 | 0.046* | |
H11 | 0.0255 | 0.4564 | 0.4199 | 0.050* | |
H12 | 0.1856 | 0.5539 | 0.2771 | 0.047* | |
H14A | 0.7847 | 0.9421 | 0.3271 | 0.045* | |
H14B | 0.5932 | 0.9143 | 0.3648 | 0.045* | |
H16 | 0.6726 | 1.1165 | 0.4035 | 0.046* | |
H17 | 0.7163 | 1.2788 | 0.4747 | 0.051* | |
H18 | 0.8112 | 1.2131 | 0.5951 | 0.049* | |
H20 | 0.8103 | 0.8151 | 0.5789 | 0.044* | |
H21B | 0.9928 | 0.8009 | 0.6582 | 0.041* | |
H21A | 0.8109 | 0.7745 | 0.7138 | 0.041* | |
H22 | 0.2008 | 0.9756 | 0.1744 | 0.061* | |
H23 | 0.9728 | 0.6611 | −0.0668 | 0.056* | |
H24 | 0.5652 | 0.1407 | 0.1436 | 0.053* | |
H25 | 0.2284 | 0.4128 | 0.5049 | 0.047* | |
H1W1 | 0.777 (3) | 0.492 (3) | 0.3177 (16) | 0.055* | |
H1W2 | 0.829 (2) | 0.418 (3) | 0.2563 (16) | 0.055* | |
H2W1 | 0.829 (3) | 1.033 (4) | 0.145 (2) | 0.085* | |
H2W2 | 0.707 (4) | 0.928 (3) | 0.1750 (19) | 0.085* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.03290 (18) | 0.03324 (19) | 0.02119 (15) | 0.00179 (13) | −0.00785 (13) | −0.00789 (12) |
N1 | 0.0426 (13) | 0.0380 (13) | 0.0313 (11) | 0.0054 (10) | −0.0147 (10) | −0.0032 (9) |
N2 | 0.0511 (15) | 0.0396 (15) | 0.0648 (17) | 0.0163 (12) | −0.0159 (14) | −0.0175 (13) |
N3 | 0.0367 (12) | 0.0436 (14) | 0.0281 (10) | 0.0030 (10) | −0.0079 (10) | −0.0090 (10) |
N4 | 0.0521 (15) | 0.0589 (17) | 0.0252 (11) | 0.0085 (12) | −0.0029 (11) | −0.0083 (11) |
N5 | 0.0348 (12) | 0.0411 (14) | 0.0370 (12) | 0.0035 (10) | −0.0109 (10) | −0.0176 (10) |
N6 | 0.0490 (14) | 0.0376 (14) | 0.0533 (14) | 0.0044 (11) | −0.0179 (12) | −0.0185 (11) |
N7 | 0.0362 (12) | 0.0361 (12) | 0.0267 (10) | 0.0051 (9) | −0.0081 (9) | −0.0070 (9) |
N8 | 0.0453 (13) | 0.0419 (14) | 0.0258 (10) | 0.0000 (11) | −0.0058 (10) | −0.0043 (9) |
O1 | 0.0526 (11) | 0.0368 (11) | 0.0249 (8) | −0.0010 (9) | −0.0182 (9) | −0.0074 (7) |
O2 | 0.0569 (12) | 0.0422 (11) | 0.0288 (9) | 0.0088 (9) | −0.0208 (9) | −0.0106 (8) |
O3 | 0.0903 (16) | 0.0364 (11) | 0.0323 (10) | 0.0006 (11) | −0.0328 (11) | −0.0107 (8) |
O4 | 0.0694 (13) | 0.0352 (11) | 0.0309 (9) | 0.0082 (9) | −0.0257 (10) | −0.0131 (8) |
O5 | 0.0580 (13) | 0.0451 (12) | 0.0436 (10) | 0.0128 (10) | −0.0287 (10) | −0.0205 (9) |
O6 | 0.0448 (11) | 0.0434 (12) | 0.0335 (9) | 0.0143 (9) | −0.0120 (9) | −0.0111 (8) |
O1W | 0.0391 (10) | 0.0439 (12) | 0.0320 (9) | 0.0101 (9) | −0.0118 (9) | −0.0156 (8) |
O2W | 0.0636 (15) | 0.0411 (13) | 0.0683 (15) | 0.0012 (11) | −0.0298 (13) | −0.0033 (11) |
C1 | 0.062 (2) | 0.0472 (18) | 0.0405 (15) | 0.0139 (15) | −0.0119 (15) | −0.0147 (13) |
C2 | 0.076 (2) | 0.064 (2) | 0.0522 (18) | 0.0180 (19) | −0.0318 (19) | −0.0112 (17) |
C3 | 0.069 (2) | 0.064 (2) | 0.0372 (15) | 0.0241 (18) | −0.0152 (16) | −0.0164 (15) |
C4 | 0.0418 (15) | 0.0481 (17) | 0.0281 (12) | 0.0057 (13) | −0.0073 (12) | −0.0106 (12) |
C5 | 0.056 (2) | 0.081 (3) | 0.053 (2) | −0.0202 (19) | 0.0081 (17) | −0.0185 (19) |
C6 | 0.0525 (19) | 0.078 (3) | 0.0431 (16) | −0.0166 (18) | −0.0017 (15) | −0.0232 (16) |
C7 | 0.0520 (18) | 0.053 (2) | 0.067 (2) | 0.0077 (15) | −0.0329 (17) | −0.0262 (16) |
C8 | 0.0450 (16) | 0.0528 (19) | 0.0422 (15) | −0.0019 (14) | −0.0164 (14) | −0.0172 (14) |
C9 | 0.0447 (16) | 0.0479 (18) | 0.0451 (15) | 0.0075 (13) | −0.0207 (14) | −0.0172 (13) |
C10 | 0.0383 (15) | 0.0448 (17) | 0.0309 (13) | 0.0024 (12) | −0.0101 (12) | −0.0045 (12) |
C11 | 0.0353 (14) | 0.0499 (18) | 0.0392 (14) | 0.0009 (13) | −0.0046 (13) | −0.0133 (13) |
C12 | 0.0387 (15) | 0.0510 (18) | 0.0300 (13) | 0.0053 (13) | −0.0112 (12) | −0.0105 (12) |
C13 | 0.0322 (13) | 0.0402 (15) | 0.0239 (11) | −0.0025 (11) | −0.0081 (11) | −0.0087 (10) |
C14 | 0.0539 (17) | 0.0374 (15) | 0.0279 (12) | −0.0023 (13) | −0.0182 (12) | −0.0098 (11) |
C15 | 0.0443 (15) | 0.0365 (15) | 0.0276 (12) | 0.0008 (12) | −0.0127 (12) | −0.0121 (11) |
C16 | 0.0489 (16) | 0.0416 (16) | 0.0284 (12) | 0.0051 (13) | −0.0170 (12) | −0.0071 (11) |
C17 | 0.0605 (18) | 0.0301 (15) | 0.0368 (14) | 0.0073 (13) | −0.0154 (14) | −0.0075 (11) |
C18 | 0.0594 (18) | 0.0326 (15) | 0.0344 (13) | 0.0064 (13) | −0.0147 (13) | −0.0149 (11) |
C19 | 0.0443 (15) | 0.0370 (15) | 0.0268 (12) | 0.0042 (12) | −0.0115 (12) | −0.0116 (11) |
C20 | 0.0526 (17) | 0.0302 (14) | 0.0290 (12) | 0.0021 (12) | −0.0138 (12) | −0.0078 (10) |
C21 | 0.0465 (15) | 0.0324 (14) | 0.0274 (12) | 0.0044 (12) | −0.0117 (12) | −0.0110 (10) |
C22 | 0.0274 (12) | 0.0424 (16) | 0.0272 (12) | 0.0049 (11) | −0.0054 (11) | −0.0111 (11) |
Geometric parameters (Å, º) top
Ni1—N1 | 2.092 (2) | O1W—H1W1 | 0.85 (3) |
Ni1—N3 | 2.094 (2) | O1W—H1W2 | 0.85 (3) |
Ni1—N5 | 2.090 (2) | O2W—H2W1 | 0.85 (3) |
Ni1—N7 | 2.101 (2) | O2W—H2W2 | 0.85 (3) |
Ni1—O1 | 2.143 (2) | C1—H1 | 0.9300 |
Ni1—O1W | 2.140 (2) | C2—C3 | 1.362 (5) |
O1—C13 | 1.272 (3) | C2—H2 | 0.9300 |
O2—C13 | 1.249 (3) | C3—H3 | 0.9300 |
O5—C22 | 1.241 (3) | C4—H4 | 0.9300 |
O6—C22 | 1.255 (3) | C5—C6 | 1.352 (5) |
N1—C1 | 1.348 (4) | C5—H5 | 0.9300 |
N1—C3 | 1.348 (4) | C6—H6 | 0.9300 |
N2—C1 | 1.322 (4) | C7—H7 | 0.9300 |
N2—C2 | 1.375 (4) | C8—C9 | 1.346 (4) |
N2—H22 | 0.8600 | C8—H8 | 0.9300 |
N3—C4 | 1.327 (3) | C9—H9 | 0.9300 |
N3—C6 | 1.358 (4) | C10—H10 | 0.9300 |
N4—C4 | 1.323 (4) | C11—C12 | 1.354 (4) |
N4—C5 | 1.357 (4) | C11—H11 | 0.9300 |
N4—H23 | 0.8600 | C12—H12 | 0.9300 |
N5—C7 | 1.307 (4) | C13—C14 | 1.511 (4) |
N5—C9 | 1.374 (3) | C14—H14A | 0.9700 |
N6—C7 | 1.331 (4) | C14—H14B | 0.9700 |
N6—C8 | 1.359 (4) | C15—C16 | 1.369 (4) |
N6—H24 | 0.8600 | C15—C20 | 1.399 (3) |
N7—C10 | 1.316 (3) | C16—C17 | 1.391 (4) |
N7—C12 | 1.385 (3) | C16—H16 | 0.9300 |
N8—C10 | 1.330 (4) | C17—C18 | 1.383 (4) |
N8—C11 | 1.364 (4) | C17—H17 | 0.9300 |
N8—H25 | 0.8600 | C18—C19 | 1.390 (4) |
O3—C15 | 1.371 (3) | C18—H18 | 0.9300 |
O3—C14 | 1.420 (3) | C19—C20 | 1.380 (4) |
O4—C19 | 1.381 (3) | C20—H20 | 0.9300 |
O4—C21 | 1.425 (3) | C21—C22 | 1.524 (3) |
O5—C22 | 1.241 (3) | C21—H21B | 0.9700 |
O6—C22 | 1.255 (3) | C21—H21A | 0.9700 |
N1—Ni1—N3 | 92.89 (9) | C3—C2—N2 | 104.9 (3) |
N1—Ni1—N7 | 89.90 (9) | C3—C2—H2 | 127.5 |
N1—Ni1—O1 | 84.99 (8) | C4—N3—Ni1 | 125.7 (2) |
N1—Ni1—O1W | 172.46 (8) | C4—N4—C5 | 106.8 (2) |
N3—Ni1—N7 | 176.75 (9) | C4—N3—C6 | 104.3 (2) |
N3—Ni1—O1 | 90.55 (8) | C4—N4—H23 | 126.6 |
N3—Ni1—O1W | 89.25 (8) | C5—N4—H23 | 126.6 |
N5—Ni1—N1 | 96.40 (9) | C5—C6—N3 | 110.1 (3) |
N5—Ni1—N3 | 89.41 (9) | C5—C6—H6 | 124.9 |
N5—Ni1—N7 | 88.63 (9) | C6—N3—Ni1 | 129.7 (2) |
N5—Ni1—O1 | 178.62 (8) | C6—C5—N4 | 106.4 (3) |
N5—Ni1—O1W | 90.85 (8) | C6—C5—H5 | 126.8 |
N7—Ni1—O1 | 91.35 (8) | C7—N5—Ni1 | 122.4 (2) |
N7—Ni1—O1W | 88.19 (8) | C7—N5—C9 | 104.2 (2) |
O1W—Ni1—O1 | 87.77 (7) | C7—N6—C8 | 106.8 (3) |
Ni1—O1W—H1W1 | 107 (2) | C7—N6—H24 | 126.6 |
Ni1—O1W—H1W2 | 116 (2) | C8—N6—H24 | 126.6 |
N1—C1—H1 | 124.0 | C8—C9—N5 | 110.2 (3) |
N1—C3—C2 | 111.6 (3) | C8—C9—H9 | 124.9 |
N1—C3—H3 | 124.2 | C9—N5—Ni1 | 133.4 (2) |
N2—C1—N1 | 112.0 (3) | C9—C8—N6 | 106.0 (2) |
N2—C1—H1 | 124.0 | C9—C8—H8 | 127.0 |
N2—C2—H2 | 127.5 | C10—N7—Ni1 | 128.3 (2) |
N3—C4—H4 | 123.8 | C10—N7—C12 | 104.0 (2) |
N3—C6—H6 | 124.9 | C10—N8—C11 | 107.2 (2) |
N4—C4—N3 | 112.4 (3) | C10—N8—H25 | 126.4 |
N4—C4—H4 | 123.8 | C11—N8—H25 | 126.4 |
N4—C5—H5 | 126.8 | C11—C12—N7 | 110.0 (2) |
N5—C7—N6 | 112.8 (3) | C11—C12—H12 | 125.0 |
N5—C7—H7 | 123.6 | C12—N7—Ni1 | 127.4 (2) |
N5—C9—H9 | 124.9 | C12—C11—N8 | 106.0 (2) |
N6—C7—H7 | 123.6 | C12—C11—H11 | 127.0 |
N6—C8—H8 | 127.0 | C13—O1—Ni1 | 129.4 (2) |
N7—C10—N8 | 112.8 (2) | C13—C14—H14A | 109.9 |
N7—C10—H10 | 123.6 | C13—C14—H14B | 109.9 |
N7—C12—H12 | 125.0 | C15—O3—C14 | 119.4 (2) |
N8—C10—H10 | 123.6 | C15—C16—C17 | 118.3 (2) |
N8—C11—H11 | 127.0 | C15—C16—H16 | 120.8 |
O1—C13—C14 | 115.0 (2) | C15—C20—H20 | 120.1 |
O2—C13—O1 | 125.0 (2) | C16—C15—O3 | 125.7 (2) |
O2—C13—C14 | 120.0 (2) | C16—C15—C20 | 120.9 (2) |
O3—C14—C13 | 108.7 (2) | C16—C17—H17 | 119.0 |
O3—C14—H14A | 109.9 | C17—C16—H16 | 120.8 |
O3—C14—H14B | 109.9 | C17—C18—C19 | 118.8 (2) |
O3—C15—C20 | 113.4 (2) | C17—C18—H18 | 120.6 |
O4—C19—C18 | 116.4 (2) | C18—C17—C16 | 121.9 (3) |
O4—C21—C22 | 110.9 (2) | C18—C17—H17 | 119.0 |
O4—C21—H21A | 109.5 | C19—O4—C21 | 116.2 (2) |
O4—C21—H21B | 109.5 | C19—C18—H18 | 120.6 |
O5—C22—O6 | 125.0 (2) | C19—C20—C15 | 119.9 (3) |
O5—C22—C21 | 120.2 (2) | C19—C20—H20 | 120.1 |
O6—C22—C21 | 114.8 (2) | C20—C19—O4 | 123.6 (2) |
C1—N1—Ni1 | 122.0 (2) | C20—C19—C18 | 120.1 (2) |
C1—N2—C2 | 107.5 (3) | C22—C21—H21A | 109.5 |
C1—N2—H22 | 126.3 | C22—C21—H21B | 109.5 |
C2—N2—H22 | 126.3 | H1W1—O1W—H1W2 | 110 (2) |
C2—C3—H3 | 124.2 | H2W1—O2W—H2W2 | 111 (2) |
C3—N1—Ni1 | 134.0 (2) | H14A—C14—H14B | 108.3 |
C3—N1—C1 | 104.0 (2) | H21B—C21—H21A | 108.0 |
Ni1—N1—C1—N2 | −179.6 (2) | O1—C13—C14—O3 | 171.7 (2) |
Ni1—N1—C3—C2 | −179.7 (2) | O2—C13—C14—O3 | −8.9 (4) |
Ni1—N3—C4—N4 | 173.31 (19) | O3—C15—C16—C17 | −177.9 (3) |
Ni1—N3—C6—C5 | −173.4 (3) | O3—C15—C20—C19 | 177.6 (3) |
Ni1—N5—C7—N6 | 178.8 (2) | O4—C19—C20—C15 | −178.2 (3) |
Ni1—N5—C9—C8 | −177.7 (2) | O4—C21—C22—O5 | 2.8 (4) |
Ni1—N7—C10—N8 | −174.32 (18) | O4—C21—C22—O6 | −177.8 (2) |
Ni1—N7—C12—C11 | 174.1 (2) | O1W—Ni1—N3—C4 | 117.9 (2) |
Ni1—O1—C13—O2 | 22.1 (4) | O1W—Ni1—N3—C6 | −68.2 (3) |
Ni1—O1—C13—C14 | −158.57 (18) | O1W—Ni1—N5—C7 | −13.3 (3) |
N1—Ni1—N3—C4 | −69.4 (2) | O1W—Ni1—N5—C9 | 163.9 (3) |
N1—Ni1—N3—C6 | 104.5 (3) | O1W—Ni1—N7—C10 | 24.9 (2) |
N1—Ni1—N5—C7 | 168.8 (3) | O1W—Ni1—N7—C12 | −147.9 (2) |
N1—Ni1—N5—C9 | −14.0 (3) | O1W—Ni1—O1—C13 | −29.4 (2) |
N1—Ni1—N7—C10 | −147.9 (2) | C1—N1—C3—C2 | −0.7 (4) |
N1—Ni1—N7—C12 | 39.4 (2) | C1—N2—C2—C3 | 0.8 (4) |
N1—Ni1—O1—C13 | 148.5 (2) | C2—N2—C1—N1 | −1.3 (4) |
N2—C2—C3—N1 | 0.0 (4) | C3—N1—C1—N2 | 1.2 (4) |
N3—Ni1—N1—C1 | −140.4 (2) | C4—N4—C5—C6 | −0.4 (4) |
N3—Ni1—N1—C3 | 38.4 (3) | C4—N3—C6—C5 | 1.5 (4) |
N3—Ni1—N5—C7 | 76.0 (3) | C5—N4—C4—N3 | 1.5 (4) |
N3—Ni1—N5—C9 | −106.9 (3) | C6—N3—C4—N4 | −1.9 (3) |
N3—Ni1—O1—C13 | −118.7 (2) | C7—N5—C9—C8 | −0.1 (4) |
N4—C5—C6—N3 | −0.7 (5) | C7—N6—C8—C9 | 1.2 (3) |
N5—Ni1—N1—C1 | 129.8 (2) | C8—N6—C7—N5 | −1.4 (4) |
N5—Ni1—N1—C3 | −51.3 (3) | C9—N5—C7—N6 | 0.9 (4) |
N5—Ni1—N3—C4 | 27.0 (2) | C10—N7—C12—C11 | −0.1 (3) |
N5—Ni1—N3—C6 | −159.1 (3) | C10—N8—C11—C12 | −0.4 (3) |
N5—Ni1—N7—C10 | 115.7 (2) | C11—N8—C10—N7 | 0.4 (3) |
N5—Ni1—N7—C12 | −57.0 (2) | C12—N7—C10—N8 | −0.2 (3) |
N6—C8—C9—N5 | −0.7 (3) | C14—O3—C15—C16 | 9.9 (4) |
N7—Ni1—N1—C1 | 41.2 (2) | C14—O3—C15—C20 | −170.5 (2) |
N7—Ni1—N1—C3 | −139.9 (3) | C15—O3—C14—C13 | 172.2 (2) |
N7—Ni1—N5—C7 | −101.5 (3) | C15—C16—C17—C18 | −0.4 (5) |
N7—Ni1—N5—C9 | 75.7 (3) | C16—C15—C20—C19 | −2.8 (4) |
O1—Ni1—N7—C10 | −62.9 (2) | C16—C17—C18—C19 | −1.3 (5) |
N7—Ni1—O1—C13 | 58.7 (2) | C17—C18—C19—O4 | −179.7 (3) |
N8—C11—C12—N7 | 0.3 (3) | C17—C18—C19—C20 | 1.0 (4) |
O1—Ni1—N1—C1 | −50.1 (2) | C18—C19—C20—C15 | 1.0 (4) |
O1—Ni1—N1—C3 | 128.7 (3) | C19—O4—C21—C22 | 177.7 (2) |
O1—Ni1—N3—C4 | −154.4 (2) | C20—C15—C16—C17 | 2.5 (4) |
O1—Ni1—N3—C6 | 19.5 (3) | C21—O4—C19—C18 | −176.7 (2) |
O1—Ni1—N7—C12 | 124.4 (2) | C21—O4—C19—C20 | 2.5 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H22···O5i | 0.86 | 1.88 | 2.720 (3) | 164 |
N4—H23···O6ii | 0.86 | 2.02 | 2.869 (3) | 170 |
N6—H24···O2Wiii | 0.86 | 1.96 | 2.739 (4) | 151 |
N8—H25···O2iv | 0.86 | 1.96 | 2.792 (3) | 163 |
N8—H25···O3iv | 0.86 | 2.52 | 3.001 (3) | 116 |
O1W—H1W1···O2 | 0.85 (3) | 1.90 (3) | 2.688 (3) | 154 (3) |
O1W—H1W2···O6v | 0.85 (3) | 1.92 (3) | 2.758 (3) | 167 (3) |
O2W—H2W1···O5vi | 0.85 (3) | 2.02 (3) | 2.857 (3) | 167 (4) |
O2W—H2W2···O1 | 0.85 (3) | 2.02 (3) | 2.854 (3) | 168 (3) |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x, y, z−1; (iii) x, y−1, z; (iv) −x+1, −y+1, −z+1; (v) −x+2, −y+1, −z+1; (vi) −x+2, −y+2, −z+1. |