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Reaction of the flexible phenolic carboxylate ligand 2-(3,5-dicarboxylbenzyloxy)benzoic acid (H3L) with nickel salts in the presence of 1,2-bis(pyridin-4-yl)ethylene (bpe) leads to the generation of a mixture of the two complexes under solvolthermal conditions, namely poly[[aqua[μ-1,2-bis(pyridin-4-yl)ethylene-κ2N:N′]{μ-5-[(2-carboxyphenoxy)methyl]benzene-1,3-dicarboxylato-κ3O1,O1′:O3}nickel(II)] dimethylformamide hemisolvate monohydrate], {[Ni(C16H10O7)(C12H10N2)(H2O)]·0.5C3H7NO·H2O}n or {[Ni(HL)(bpe)(H2O)]·0.5DMF·H2O}n, 1, and poly[[diaquatris[μ-1,2-bis(pyridin-4-yl)ethylene-κ2N:N′]bis{μ-5-[(2-carboxyphenoxy)methyl]benzene-1,3-dicarboxylato-κ2O1:O5}nickel(II)] dimethylformamide disolvate hexahydrate], {[Ni2(C16H10O7)2(C12H10N2)3(H2O)2]·2C3H7NO·6H2O}n or {[Ni2(HL)2(bpe)3(H2O)2]·2DMF·6H2O}n, 2. In complex 1, the NiII centres are connected by the carboxylate and bpe ligands to form two-dimensional (2D) 4-connected (4,4) layers, which are extended into a 2D+2D→3D (3D is three-dimensional) supramolecular framework. In complex 2, bpe ligands connect to NiII centres to form 2D layers with Ni6(bpe)6 metallmacrocycles. Interestingly, 2D+2D→3D inclined polycatenation was observed between these layers. The final 5-connected 3D self-penetrating structure was generated through further connection of Ni–carboxylate chains with these inclined motifs. Both complexes were fully characterized by single-crystal analysis, powder X-ray diffraction analysis, FT–IR spectra, elemental analyses, thermal analysis and UV–Vis spectra. Notably, an interesting metal/ligand-induced crystal-to-crystal transformation was observed between the two complexes.
Supporting information
CCDC references: 1901755; 1901754
For both structures, data collection: SMART (Bruker, 2008); cell refinement: SMART (Bruker, 2008). Data reduction: SHELXTL (Bruker, 2008) for 1901754; SAINT (Bruker, 2008) for 1901755. For both structures, program(s) used to solve structure: SHELXS2014 (Sheldrick, 2014); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Bruker, 2008); software used to prepare material for publication: SHELXTL (Bruker, 2008).
Poly[[aqua[µ-1,2-bis(pyridin-4-yl)ethylene-
κ2N:
N']{µ-5-[(2-carboxyphenoxy)methyl]benzene-1,3-dicarboxylato-
κ3O1,
O1':
O3}nickel(II)] dimethylformamide
hemisolvate monohydrate] (1901754)
top
Crystal data top
[Ni(C16H10O7)(C12H10N2)(H2O)]·0.5C3H7NO·H2O | Z = 2 |
Mr = 627.75 | F(000) = 652 |
Triclinic, P1 | Dx = 1.353 Mg m−3 |
a = 10.2700 (8) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.9701 (9) Å | Cell parameters from 1944 reflections |
c = 12.5459 (11) Å | θ = 2.6–22.5° |
α = 90.821 (1)° | µ = 0.69 mm−1 |
β = 91.089 (1)° | T = 298 K |
γ = 92.278 (2)° | Block, green |
V = 1540.6 (2) Å3 | 0.37 × 0.30 × 0.15 mm |
Data collection top
Bruker SMART CCD area detector diffractometer | 3700 reflections with I > 2σ(I) |
phi and ω scans | Rint = 0.046 |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | θmax = 25.0°, θmin = 2.3° |
Tmin = 0.781, Tmax = 0.902 | h = −11→12 |
7884 measured reflections | k = −13→14 |
5367 independent reflections | l = −8→14 |
Refinement top
Refinement on F2 | 110 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.079 | H-atom parameters constrained |
wR(F2) = 0.234 | w = 1/[σ2(Fo2) + (0.1535P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max < 0.001 |
5367 reflections | Δρmax = 1.19 e Å−3 |
410 parameters | Δρmin = −0.47 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Ni1 | 0.06023 (6) | 0.49966 (5) | 0.75087 (5) | 0.0334 (3) | |
N1 | 0.0598 (4) | 0.3376 (4) | 0.8169 (4) | 0.0431 (11) | |
N2 | 0.0506 (4) | 0.6590 (4) | 0.6803 (3) | 0.0374 (10) | |
N3 | 0.3896 (9) | 0.7223 (10) | 0.0255 (9) | 0.065 (3) | 0.5 |
O1 | 0.2650 (3) | 0.5160 (3) | 0.7745 (3) | 0.0416 (9) | |
O2 | 0.1804 (3) | 0.4398 (3) | 0.6261 (3) | 0.0391 (9) | |
O3 | 0.8769 (3) | 0.4651 (3) | 0.6947 (3) | 0.0412 (9) | |
O4 | 0.7594 (4) | 0.5610 (4) | 0.8100 (4) | 0.0614 (12) | |
O5 | 0.6043 (4) | 0.1717 (3) | 0.4660 (3) | 0.0611 (12) | |
O6 | 0.7126 (5) | −0.1189 (5) | 0.5999 (5) | 0.101 (2) | |
O7 | 0.6920 (6) | 0.0615 (5) | 0.6250 (4) | 0.0916 (17) | |
H7A | 0.6779 | 0.1172 | 0.5900 | 0.137* | |
O8 | −0.0023 (3) | 0.5605 (3) | 0.8975 (3) | 0.0445 (9) | |
H8C | −0.0850 | 0.5617 | 0.8966 | 0.067* | |
H8E | 0.0297 | 0.6263 | 0.9080 | 0.067* | |
O9 | 0.7057 (12) | 0.7999 (9) | 0.8072 (7) | 0.241 (6) | |
H9E | 0.7078 | 0.8231 | 0.7436 | 0.290* | |
H9F | 0.7213 | 0.7307 | 0.8066 | 0.290* | |
O10 | 0.1789 (10) | 0.6967 (10) | −0.0150 (9) | 0.088 (3) | 0.5 |
C1 | 0.2789 (5) | 0.4673 (4) | 0.6846 (4) | 0.0328 (11) | |
C2 | 0.4136 (5) | 0.4405 (4) | 0.6495 (4) | 0.0354 (12) | |
C3 | 0.5231 (5) | 0.4806 (4) | 0.7057 (4) | 0.0365 (12) | |
H3 | 0.5142 | 0.5238 | 0.7672 | 0.044* | |
C4 | 0.6484 (5) | 0.4562 (5) | 0.6698 (4) | 0.0395 (13) | |
C5 | 0.7724 (5) | 0.4982 (5) | 0.7311 (4) | 0.0409 (13) | |
C6 | 0.6599 (5) | 0.3914 (5) | 0.5791 (4) | 0.0410 (13) | |
H6 | 0.7423 | 0.3746 | 0.5557 | 0.049* | |
C7 | 0.4267 (5) | 0.3768 (4) | 0.5560 (4) | 0.0384 (12) | |
H7 | 0.3529 | 0.3522 | 0.5169 | 0.046* | |
C8 | 0.5496 (5) | 0.3502 (5) | 0.5216 (4) | 0.0399 (13) | |
C9 | 0.5660 (6) | 0.2761 (5) | 0.4247 (5) | 0.0485 (14) | |
H9A | 0.4848 | 0.2669 | 0.3843 | 0.058* | |
H9B | 0.6325 | 0.3076 | 0.3788 | 0.058* | |
C10 | 0.6238 (6) | 0.0822 (5) | 0.3981 (6) | 0.0551 (16) | |
C11 | 0.6046 (7) | 0.0866 (7) | 0.2894 (6) | 0.072 (2) | |
H11 | 0.5765 | 0.1514 | 0.2578 | 0.086* | |
C12 | 0.6281 (9) | −0.0076 (8) | 0.2275 (7) | 0.095 (3) | |
H12 | 0.6139 | −0.0057 | 0.1541 | 0.114* | |
C13 | 0.6720 (9) | −0.1038 (7) | 0.2731 (9) | 0.098 (3) | |
H13 | 0.6914 | −0.1651 | 0.2307 | 0.117* | |
C14 | 0.6860 (7) | −0.1073 (6) | 0.3791 (8) | 0.083 (2) | |
H14 | 0.7103 | −0.1738 | 0.4097 | 0.099* | |
C15 | 0.6660 (6) | −0.0153 (5) | 0.4460 (6) | 0.0607 (18) | |
C16 | 0.6912 (7) | −0.0278 (7) | 0.5605 (7) | 0.072 (2) | |
C17 | 0.0457 (10) | 0.0408 (8) | 1.0023 (10) | 0.072 (3) | 0.515 (12) |
H17 | 0.1130 | 0.0426 | 1.0530 | 0.086* | 0.515 (12) |
C18 | 0.0331 (9) | 0.1303 (6) | 0.9201 (7) | 0.083 (2) | |
C19 | −0.0374 (9) | 0.1524 (6) | 0.8286 (7) | 0.083 (2) | |
H19 | −0.0955 | 0.0978 | 0.8002 | 0.100* | |
C20 | −0.0230 (7) | 0.2553 (5) | 0.7780 (6) | 0.0639 (18) | |
H20 | −0.0714 | 0.2676 | 0.7161 | 0.077* | |
C21 | 0.1342 (6) | 0.3146 (5) | 0.9013 (5) | 0.0550 (16) | |
H21 | 0.1969 | 0.3676 | 0.9257 | 0.066* | |
C22 | 0.1206 (9) | 0.2135 (7) | 0.9540 (6) | 0.081 (2) | |
H22 | 0.1725 | 0.2020 | 1.0141 | 0.098* | |
C23 | 0.0124 (7) | 0.9858 (7) | 0.5486 (5) | 0.094 (3) | |
H23 | 0.0241 | 1.0436 | 0.5986 | 0.113* | |
C24 | 0.0242 (6) | 0.8693 (6) | 0.5885 (7) | 0.069 (2) | |
C25 | 0.0657 (7) | 0.8576 (6) | 0.6891 (7) | 0.071 (2) | |
H25 | 0.0855 | 0.9213 | 0.7305 | 0.085* | |
C26 | 0.0797 (6) | 0.7567 (5) | 0.7324 (5) | 0.0537 (16) | |
H26 | 0.1113 | 0.7539 | 0.8022 | 0.064* | |
C27 | 0.0067 (6) | 0.6668 (5) | 0.5816 (5) | 0.0528 (16) | |
H27 | −0.0160 | 0.6015 | 0.5434 | 0.063* | |
C28 | −0.0072 (7) | 0.7701 (7) | 0.5320 (6) | 0.074 (2) | |
H28 | −0.0373 | 0.7726 | 0.4617 | 0.088* | |
C29 | 0.2837 (12) | 0.6669 (14) | −0.0078 (12) | 0.078 (3) | 0.5 |
H29 | 0.2948 | 0.5930 | −0.0286 | 0.094* | 0.5 |
C30 | 0.3695 (18) | 0.8181 (14) | 0.0925 (16) | 0.126 (5) | 0.5 |
H30A | 0.3325 | 0.8388 | 0.1593 | 0.188* | 0.5 |
H30B | 0.3224 | 0.8517 | 0.0352 | 0.188* | 0.5 |
H30C | 0.4592 | 0.8436 | 0.0915 | 0.188* | 0.5 |
C31 | 0.5098 (14) | 0.6639 (16) | 0.0264 (16) | 0.115 (5) | 0.5 |
H31A | 0.4969 | 0.5850 | 0.0132 | 0.173* | 0.5 |
H31B | 0.5578 | 0.6763 | 0.0922 | 0.173* | 0.5 |
H31C | 0.5577 | 0.6969 | −0.0310 | 0.173* | 0.5 |
C17' | −0.0188 (14) | 0.0155 (9) | 0.9518 (6) | 0.072 (3) | 0.485 (12) |
H17' | −0.0727 | −0.0295 | 0.9073 | 0.086* | 0.485 (12) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni1 | 0.0222 (4) | 0.0342 (4) | 0.0438 (5) | 0.0003 (3) | 0.0007 (3) | 0.0086 (3) |
N1 | 0.040 (3) | 0.040 (3) | 0.050 (3) | 0.002 (2) | 0.013 (2) | 0.010 (2) |
N2 | 0.028 (2) | 0.040 (3) | 0.045 (3) | 0.0000 (19) | 0.0028 (19) | 0.014 (2) |
N3 | 0.033 (4) | 0.094 (7) | 0.066 (6) | −0.007 (5) | −0.016 (4) | −0.018 (5) |
O1 | 0.0234 (18) | 0.053 (2) | 0.048 (2) | −0.0005 (16) | −0.0012 (16) | 0.0010 (18) |
O2 | 0.0241 (18) | 0.049 (2) | 0.044 (2) | −0.0006 (16) | −0.0011 (15) | 0.0031 (17) |
O3 | 0.0184 (17) | 0.049 (2) | 0.056 (2) | 0.0000 (15) | 0.0005 (16) | −0.0009 (18) |
O4 | 0.030 (2) | 0.081 (3) | 0.073 (3) | 0.011 (2) | −0.011 (2) | −0.026 (3) |
O5 | 0.070 (3) | 0.049 (3) | 0.065 (3) | 0.012 (2) | −0.002 (2) | −0.006 (2) |
O6 | 0.076 (4) | 0.090 (4) | 0.139 (5) | 0.016 (3) | 0.015 (3) | 0.046 (4) |
O7 | 0.105 (5) | 0.090 (4) | 0.080 (4) | 0.011 (3) | −0.007 (3) | 0.012 (3) |
O8 | 0.0328 (19) | 0.051 (2) | 0.050 (2) | 0.0002 (17) | 0.0041 (17) | 0.0007 (18) |
O9 | 0.379 (17) | 0.246 (12) | 0.110 (7) | 0.168 (11) | −0.036 (8) | 0.009 (7) |
O10 | 0.061 (5) | 0.108 (7) | 0.091 (6) | −0.012 (5) | −0.001 (5) | −0.036 (5) |
C1 | 0.025 (3) | 0.034 (3) | 0.039 (3) | −0.003 (2) | 0.000 (2) | 0.008 (2) |
C2 | 0.021 (2) | 0.040 (3) | 0.045 (3) | 0.000 (2) | 0.001 (2) | 0.005 (2) |
C3 | 0.029 (3) | 0.042 (3) | 0.039 (3) | 0.003 (2) | 0.005 (2) | −0.002 (2) |
C4 | 0.018 (2) | 0.046 (3) | 0.054 (3) | 0.002 (2) | −0.003 (2) | 0.002 (3) |
C5 | 0.035 (3) | 0.040 (3) | 0.046 (3) | −0.006 (2) | −0.002 (2) | 0.003 (3) |
C6 | 0.025 (3) | 0.049 (3) | 0.049 (3) | 0.005 (2) | 0.002 (2) | 0.002 (3) |
C7 | 0.028 (3) | 0.042 (3) | 0.045 (3) | −0.004 (2) | −0.001 (2) | 0.004 (2) |
C8 | 0.033 (3) | 0.040 (3) | 0.047 (3) | −0.001 (2) | 0.002 (2) | 0.000 (2) |
C9 | 0.039 (3) | 0.054 (4) | 0.052 (4) | 0.003 (3) | 0.004 (3) | −0.004 (3) |
C10 | 0.040 (3) | 0.052 (4) | 0.073 (5) | −0.006 (3) | 0.000 (3) | −0.010 (3) |
C11 | 0.061 (4) | 0.076 (5) | 0.078 (5) | −0.003 (4) | 0.002 (4) | −0.023 (4) |
C12 | 0.090 (6) | 0.111 (8) | 0.083 (6) | −0.002 (6) | 0.012 (5) | −0.030 (6) |
C13 | 0.104 (7) | 0.066 (6) | 0.123 (8) | 0.012 (5) | 0.006 (6) | −0.038 (6) |
C14 | 0.061 (5) | 0.054 (5) | 0.133 (8) | −0.003 (4) | 0.008 (5) | −0.004 (5) |
C15 | 0.039 (3) | 0.046 (4) | 0.097 (6) | −0.002 (3) | 0.008 (3) | −0.003 (4) |
C16 | 0.044 (4) | 0.063 (5) | 0.109 (7) | 0.001 (3) | 0.010 (4) | 0.019 (5) |
C17 | 0.092 (6) | 0.048 (5) | 0.077 (6) | 0.014 (4) | 0.022 (5) | 0.025 (4) |
C18 | 0.109 (5) | 0.049 (4) | 0.094 (5) | 0.018 (3) | 0.053 (4) | 0.029 (3) |
C19 | 0.101 (5) | 0.046 (4) | 0.104 (5) | 0.004 (3) | 0.041 (4) | 0.015 (3) |
C20 | 0.070 (4) | 0.043 (4) | 0.079 (5) | −0.007 (3) | 0.018 (4) | 0.008 (3) |
C21 | 0.062 (4) | 0.055 (4) | 0.050 (4) | 0.021 (3) | 0.009 (3) | 0.022 (3) |
C22 | 0.104 (5) | 0.068 (4) | 0.077 (4) | 0.037 (4) | 0.027 (4) | 0.031 (3) |
C23 | 0.057 (5) | 0.086 (6) | 0.140 (9) | 0.006 (4) | 0.016 (5) | 0.057 (6) |
C24 | 0.045 (4) | 0.045 (4) | 0.118 (7) | 0.003 (3) | 0.016 (4) | 0.034 (4) |
C25 | 0.068 (5) | 0.040 (4) | 0.106 (6) | 0.002 (3) | −0.001 (4) | 0.019 (4) |
C26 | 0.052 (4) | 0.042 (4) | 0.066 (4) | −0.009 (3) | −0.004 (3) | 0.013 (3) |
C27 | 0.054 (4) | 0.053 (4) | 0.052 (4) | 0.009 (3) | −0.003 (3) | 0.015 (3) |
C28 | 0.057 (4) | 0.096 (6) | 0.071 (5) | 0.024 (4) | 0.013 (4) | 0.041 (4) |
C29 | 0.046 (6) | 0.102 (8) | 0.086 (7) | −0.007 (6) | −0.004 (6) | −0.022 (6) |
C30 | 0.068 (8) | 0.157 (10) | 0.149 (10) | −0.014 (8) | 0.000 (8) | −0.041 (9) |
C31 | 0.076 (8) | 0.151 (10) | 0.117 (9) | −0.007 (8) | 0.006 (8) | −0.015 (9) |
C17' | 0.092 (6) | 0.048 (5) | 0.077 (6) | 0.014 (4) | 0.022 (5) | 0.025 (4) |
Geometric parameters (Å, º) top
Ni1—O3i | 2.023 (3) | C10—C15 | 1.401 (9) |
Ni1—O8 | 2.091 (4) | C11—C12 | 1.391 (11) |
Ni1—N2 | 2.119 (4) | C11—H11 | 0.9300 |
Ni1—O1 | 2.119 (3) | C12—C13 | 1.381 (12) |
Ni1—N1 | 2.120 (4) | C12—H12 | 0.9300 |
Ni1—O2 | 2.144 (4) | C13—C14 | 1.336 (12) |
N1—C21 | 1.333 (7) | C13—H13 | 0.9300 |
N1—C20 | 1.355 (8) | C14—C15 | 1.399 (11) |
N2—C27 | 1.316 (7) | C14—H14 | 0.9300 |
N2—C26 | 1.352 (7) | C15—C16 | 1.466 (11) |
N3—C29 | 1.310 (9) | C17—C17iii | 1.328 (10) |
N3—C30 | 1.436 (9) | C17—C18 | 1.505 (9) |
N3—C31 | 1.442 (9) | C17—H17 | 0.9300 |
O1—C1 | 1.276 (6) | C18—C22 | 1.373 (12) |
O2—C1 | 1.269 (6) | C18—C19 | 1.379 (12) |
O3—C5 | 1.251 (7) | C18—C17' | 1.515 (9) |
O3—Ni1ii | 2.023 (3) | C19—C20 | 1.398 (9) |
O4—C5 | 1.248 (7) | C19—H19 | 0.9300 |
O5—C10 | 1.382 (8) | C20—H20 | 0.9300 |
O5—C9 | 1.426 (7) | C21—C22 | 1.390 (9) |
O6—C16 | 1.230 (8) | C21—H21 | 0.9300 |
O7—C16 | 1.330 (10) | C22—H22 | 0.9300 |
O7—H7A | 0.8200 | C23—C23iv | 1.293 (9) |
O8—H8C | 0.8500 | C23—C24 | 1.498 (10) |
O8—H8E | 0.8498 | C23—H23 | 0.9300 |
O9—H9E | 0.8500 | C24—C25 | 1.336 (10) |
O9—H9F | 0.8501 | C24—C28 | 1.397 (11) |
O10—C29 | 1.149 (16) | C25—C26 | 1.343 (8) |
C1—C2 | 1.506 (7) | C25—H25 | 0.9300 |
C2—C3 | 1.382 (7) | C26—H26 | 0.9300 |
C2—C7 | 1.401 (8) | C27—C28 | 1.404 (9) |
C3—C4 | 1.412 (7) | C27—H27 | 0.9300 |
C3—H3 | 0.9300 | C28—H28 | 0.9300 |
C4—C6 | 1.378 (8) | C29—H29 | 0.9300 |
C4—C5 | 1.537 (7) | C30—H30A | 0.9601 |
C6—C8 | 1.400 (7) | C30—H30B | 0.9600 |
C6—H6 | 0.9300 | C30—H30C | 0.9599 |
C7—C8 | 1.389 (7) | C31—H31A | 0.9600 |
C7—H7 | 0.9300 | C31—H31B | 0.9601 |
C8—C9 | 1.511 (8) | C31—H31C | 0.9600 |
C9—H9A | 0.9700 | C17'—C17'iii | 1.325 (10) |
C9—H9B | 0.9700 | C17'—H17' | 0.9300 |
C10—C11 | 1.377 (9) | | |
| | | |
O3i—Ni1—O8 | 93.65 (14) | C13—C12—H12 | 119.4 |
O3i—Ni1—N2 | 88.08 (15) | C11—C12—H12 | 119.4 |
O8—Ni1—N2 | 92.26 (16) | C14—C13—C12 | 118.8 (8) |
O3i—Ni1—O1 | 165.91 (15) | C14—C13—H13 | 120.6 |
O8—Ni1—O1 | 100.35 (14) | C12—C13—H13 | 120.6 |
N2—Ni1—O1 | 92.89 (15) | C13—C14—C15 | 123.0 (8) |
O3i—Ni1—N1 | 88.72 (16) | C13—C14—H14 | 118.5 |
O8—Ni1—N1 | 88.46 (16) | C15—C14—H14 | 118.5 |
N2—Ni1—N1 | 176.76 (17) | C14—C15—C10 | 117.3 (7) |
O1—Ni1—N1 | 90.10 (16) | C14—C15—C16 | 117.9 (7) |
O3i—Ni1—O2 | 103.49 (14) | C10—C15—C16 | 124.9 (7) |
O8—Ni1—O2 | 162.49 (13) | O6—C16—O7 | 118.2 (8) |
N2—Ni1—O2 | 91.84 (15) | O6—C16—C15 | 122.0 (8) |
O1—Ni1—O2 | 62.44 (14) | O7—C16—C15 | 119.8 (6) |
N1—Ni1—O2 | 88.40 (16) | C17iii—C17—C18 | 115.6 (11) |
C21—N1—C20 | 117.7 (5) | C17iii—C17—H17 | 122.2 |
C21—N1—Ni1 | 121.8 (4) | C18—C17—H17 | 122.2 |
C20—N1—Ni1 | 120.4 (4) | C22—C18—C19 | 115.5 (6) |
C27—N2—C26 | 116.1 (5) | C22—C18—C17 | 104.1 (7) |
C27—N2—Ni1 | 119.6 (4) | C19—C18—C17 | 140.3 (8) |
C26—N2—Ni1 | 124.2 (4) | C22—C18—C17' | 140.6 (8) |
C29—N3—C30 | 115.6 (13) | C19—C18—C17' | 103.8 (7) |
C29—N3—C31 | 117.6 (14) | C18—C19—C20 | 121.2 (8) |
C30—N3—C31 | 122.8 (13) | C18—C19—H19 | 119.4 |
C1—O1—Ni1 | 88.9 (3) | C20—C19—H19 | 119.4 |
C1—O2—Ni1 | 88.0 (3) | N1—C20—C19 | 121.5 (7) |
C5—O3—Ni1ii | 128.0 (4) | N1—C20—H20 | 119.3 |
C10—O5—C9 | 120.5 (5) | C19—C20—H20 | 119.3 |
C16—O7—H7A | 109.5 | N1—C21—C22 | 121.8 (7) |
Ni1—O8—H8C | 109.3 | N1—C21—H21 | 119.1 |
Ni1—O8—H8E | 109.1 | C22—C21—H21 | 119.1 |
H8C—O8—H8E | 109.5 | C18—C22—C21 | 122.1 (8) |
H9E—O9—H9F | 108.4 | C18—C22—H22 | 119.0 |
O2—C1—O1 | 120.6 (5) | C21—C22—H22 | 119.0 |
O2—C1—C2 | 120.2 (5) | C23iv—C23—C24 | 126.5 (11) |
O1—C1—C2 | 119.2 (4) | C23iv—C23—H23 | 116.7 |
C3—C2—C7 | 120.1 (5) | C24—C23—H23 | 116.7 |
C3—C2—C1 | 121.1 (5) | C25—C24—C28 | 115.9 (6) |
C7—C2—C1 | 118.7 (4) | C25—C24—C23 | 117.5 (7) |
C2—C3—C4 | 120.0 (5) | C28—C24—C23 | 126.6 (7) |
C2—C3—H3 | 120.0 | C24—C25—C26 | 122.0 (7) |
C4—C3—H3 | 120.0 | C24—C25—H25 | 119.0 |
C6—C4—C3 | 119.2 (5) | C26—C25—H25 | 119.0 |
C6—C4—C5 | 119.3 (5) | C25—C26—N2 | 123.8 (6) |
C3—C4—C5 | 121.5 (5) | C25—C26—H26 | 118.1 |
O4—C5—O3 | 126.9 (5) | N2—C26—H26 | 118.1 |
O4—C5—C4 | 117.9 (5) | N2—C27—C28 | 122.3 (7) |
O3—C5—C4 | 115.2 (5) | N2—C27—H27 | 118.8 |
C4—C6—C8 | 121.2 (5) | C28—C27—H27 | 118.8 |
C4—C6—H6 | 119.4 | C24—C28—C27 | 119.8 (7) |
C8—C6—H6 | 119.4 | C24—C28—H28 | 120.1 |
C8—C7—C2 | 120.1 (5) | C27—C28—H28 | 120.1 |
C8—C7—H7 | 119.9 | O10—C29—N3 | 129.1 (16) |
C2—C7—H7 | 119.9 | O10—C29—H29 | 115.4 |
C7—C8—C6 | 119.2 (5) | N3—C29—H29 | 115.4 |
C7—C8—C9 | 121.2 (5) | N3—C30—H30A | 141.5 |
C6—C8—C9 | 119.6 (5) | N3—C30—H30B | 89.8 |
O5—C9—C8 | 105.1 (5) | H30A—C30—H30B | 109.5 |
O5—C9—H9A | 110.7 | N3—C30—H30C | 93.8 |
C8—C9—H9A | 110.7 | H30A—C30—H30C | 109.5 |
O5—C9—H9B | 110.7 | H30B—C30—H30C | 109.5 |
C8—C9—H9B | 110.7 | N3—C31—H31A | 113.0 |
H9A—C9—H9B | 108.8 | N3—C31—H31B | 111.6 |
C11—C10—O5 | 123.1 (6) | H31A—C31—H31B | 109.5 |
C11—C10—C15 | 120.8 (7) | N3—C31—H31C | 103.7 |
O5—C10—C15 | 116.1 (6) | H31A—C31—H31C | 109.5 |
C10—C11—C12 | 118.9 (8) | H31B—C31—H31C | 109.5 |
C10—C11—H11 | 120.6 | C17'iii—C17'—C18 | 114.6 (11) |
C12—C11—H11 | 120.6 | C17'iii—C17'—H17' | 122.7 |
C13—C12—C11 | 121.2 (9) | C18—C17'—H17' | 122.7 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) −x, −y, −z+2; (iv) −x, −y+2, −z+1. |
Poly[[diaquatris[µ-1,2-bis(pyridin-4-yl)ethylene-
κ2N:
N']bis{µ-5-[(2-carboxyphenoxy)methyl]benzene-1,3-dicarboxylato-
κ2O1:
O5}nickel(II)] dimethylformamide
disolvate hexahydrate] (1901755)
top
Crystal data top
[Ni2(C16H10O7)2(C12H10N2)3(H2O)2]·2C3H7NO·6H2O | F(000) = 1656 |
Mr = 1582.88 | Dx = 1.382 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.5030 (9) Å | Cell parameters from 5603 reflections |
b = 16.4391 (14) Å | θ = 2.4–26.5° |
c = 20.5549 (18) Å | µ = 0.58 mm−1 |
β = 101.816 (2)° | T = 298 K |
V = 3804.5 (6) Å3 | Lamellar, green |
Z = 2 | 0.45 × 0.40 × 0.37 mm |
Data collection top
Bruker SMART CCD area detector diffractometer | 4884 reflections with I > 2σ(I) |
phi and ω scans | Rint = 0.038 |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | θmax = 25.0°, θmin = 2.4° |
Tmin = 0.76, Tmax = 0.81 | h = −13→11 |
18858 measured reflections | k = −18→19 |
6707 independent reflections | l = −23→24 |
Refinement top
Refinement on F2 | 1259 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.046 | H-atom parameters constrained |
wR(F2) = 0.124 | w = 1/[σ2(Fo2) + (0.0542P)2 + 3.5857P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.002 |
6707 reflections | Δρmax = 1.27 e Å−3 |
491 parameters | Δρmin = −0.62 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Ni1 | 0.70945 (3) | 0.27379 (2) | 0.27495 (2) | 0.02095 (12) | |
O1 | 0.55099 (19) | 0.21412 (13) | 0.27881 (10) | 0.0311 (5) | |
O2 | 0.4249 (2) | 0.18155 (17) | 0.18476 (11) | 0.0485 (7) | |
O3 | 0.2549 (2) | 0.1491 (2) | 0.49681 (12) | 0.0614 (8) | |
H3A | 0.2752 | 0.1619 | 0.5361 | 0.092* | |
O4 | 0.4279 (3) | 0.20547 (17) | 0.49048 (12) | 0.0548 (8) | |
O5 | 0.04955 (19) | −0.01246 (13) | 0.25710 (12) | 0.0377 (6) | |
O7 | 0.12839 (18) | −0.16751 (12) | 0.21716 (10) | 0.0284 (5) | |
O6 | 0.0466 (2) | −0.24188 (15) | 0.28579 (14) | 0.0484 (7) | |
O9 | 1.0802 (4) | 1.0608 (3) | 0.1042 (2) | 0.1123 (14) | |
O8 | 0.7450 (2) | 0.19093 (12) | 0.20530 (10) | 0.0306 (5) | |
H8A | 0.7188 | 0.2094 | 0.1664 | 0.046* | |
H8B | 0.8197 | 0.1838 | 0.2110 | 0.046* | |
O10 | 0.5640 (2) | 0.19666 (16) | 0.09569 (11) | 0.0462 (6) | |
H10C | 0.5082 | 0.1920 | 0.1170 | 0.055* | |
H10A | 0.5572 | 0.2419 | 0.0752 | 0.055* | |
O11 | 0.2631 (3) | 0.2032 (2) | 0.61371 (14) | 0.0812 (11) | |
H11D | 0.1952 | 0.2242 | 0.6126 | 0.097* | |
H11A | 0.3167 | 0.2392 | 0.6239 | 0.097* | |
O12 | 0.9516 (3) | 0.7326 (3) | 0.39609 (17) | 0.0922 (12) | |
H12D | 0.9783 | 0.7422 | 0.3612 | 0.111* | |
H12A | 0.9477 | 0.6817 | 0.4022 | 0.111* | |
N1 | 0.6684 (2) | 0.35426 (15) | 0.34603 (12) | 0.0252 (6) | |
N2 | 0.6361 (2) | 0.35375 (15) | 0.19691 (12) | 0.0265 (6) | |
N3 | 0.7932 (2) | 0.19225 (16) | 0.35020 (13) | 0.0297 (6) | |
N4 | 0.9126 (5) | 0.9872 (4) | 0.0627 (2) | 0.0937 (15) | |
C16 | 0.0453 (3) | −0.18417 (19) | 0.24655 (16) | 0.0291 (7) | |
C15 | −0.0639 (3) | −0.13173 (19) | 0.23218 (16) | 0.0295 (7) | |
C14 | −0.1741 (3) | −0.1696 (2) | 0.21466 (18) | 0.0400 (8) | |
H14A | −0.1776 | −0.2261 | 0.2140 | 0.048* | |
C13 | −0.2781 (3) | −0.1256 (2) | 0.1983 (2) | 0.0500 (10) | |
H13 | −0.3509 | −0.1520 | 0.1867 | 0.060* | |
C12 | −0.2724 (3) | −0.0423 (2) | 0.1994 (2) | 0.0482 (10) | |
H12 | −0.3418 | −0.0120 | 0.1877 | 0.058* | |
C11 | −0.1645 (3) | −0.0031 (2) | 0.21770 (19) | 0.0393 (8) | |
H11 | −0.1621 | 0.0534 | 0.2184 | 0.047* | |
C10 | −0.0598 (3) | −0.04705 (19) | 0.23506 (16) | 0.0300 (7) | |
C9 | 0.0532 (3) | 0.07412 (19) | 0.26154 (18) | 0.0335 (8) | |
H9A | −0.0038 | 0.0928 | 0.2871 | 0.040* | |
H9B | 0.0318 | 0.0975 | 0.2174 | 0.040* | |
C8 | 0.1756 (3) | 0.10167 (18) | 0.29437 (16) | 0.0281 (7) | |
C6 | 0.2022 (3) | 0.11466 (19) | 0.36217 (16) | 0.0314 (7) | |
H6 | 0.1467 | 0.1010 | 0.3875 | 0.038* | |
C4 | 0.3104 (3) | 0.14782 (19) | 0.39299 (16) | 0.0315 (7) | |
C5 | 0.3379 (3) | 0.1702 (2) | 0.46498 (17) | 0.0404 (9) | |
C3 | 0.3929 (3) | 0.16655 (19) | 0.35518 (15) | 0.0295 (7) | |
H3 | 0.4663 | 0.1874 | 0.3759 | 0.035* | |
C2 | 0.3685 (3) | 0.15491 (18) | 0.28712 (15) | 0.0262 (7) | |
C7 | 0.2594 (3) | 0.12174 (18) | 0.25701 (16) | 0.0286 (7) | |
H7 | 0.2423 | 0.1129 | 0.2113 | 0.034* | |
C1 | 0.4558 (3) | 0.18543 (19) | 0.24661 (16) | 0.0284 (7) | |
C21 | 0.7711 (3) | 0.1127 (2) | 0.34664 (19) | 0.0418 (9) | |
H21 | 0.7122 | 0.0932 | 0.3123 | 0.050* | |
C22 | 0.8331 (4) | 0.0574 (3) | 0.3925 (2) | 0.0626 (12) | |
H22 | 0.8173 | 0.0020 | 0.3879 | 0.075* | |
C18 | 0.9199 (4) | 0.0866 (3) | 0.4459 (2) | 0.0645 (13) | |
C19 | 0.9387 (4) | 0.1679 (3) | 0.4493 (2) | 0.0617 (12) | |
H19 | 0.9939 | 0.1904 | 0.4841 | 0.074* | |
C20 | 0.8765 (3) | 0.2152 (2) | 0.40169 (18) | 0.0464 (9) | |
H20 | 0.8935 | 0.2705 | 0.4050 | 0.056* | |
C26 | 0.6684 (3) | 0.43501 (19) | 0.33922 (15) | 0.0306 (7) | |
H26 | 0.7029 | 0.4572 | 0.3061 | 0.037* | |
C25 | 0.6195 (3) | 0.4872 (2) | 0.37911 (16) | 0.0358 (8) | |
H25 | 0.6201 | 0.5431 | 0.3719 | 0.043* | |
C24 | 0.5696 (3) | 0.4561 (2) | 0.42986 (15) | 0.0318 (7) | |
C23 | 0.5175 (3) | 0.5112 (2) | 0.47238 (16) | 0.0376 (8) | |
H23 | 0.5084 | 0.5655 | 0.4598 | 0.045* | |
C28 | 0.5726 (3) | 0.3724 (2) | 0.43773 (16) | 0.0337 (8) | |
H28 | 0.5411 | 0.3487 | 0.4714 | 0.040* | |
C27 | 0.6219 (3) | 0.32474 (19) | 0.39611 (15) | 0.0298 (7) | |
H27 | 0.6234 | 0.2688 | 0.4028 | 0.036* | |
C33 | 0.6981 (3) | 0.3743 (2) | 0.15084 (16) | 0.0368 (8) | |
H33 | 0.7758 | 0.3557 | 0.1560 | 0.044* | |
C34 | 0.6530 (3) | 0.4213 (2) | 0.09656 (17) | 0.0420 (9) | |
H34 | 0.7002 | 0.4340 | 0.0662 | 0.050* | |
C30 | 0.5378 (3) | 0.4498 (2) | 0.08663 (16) | 0.0390 (8) | |
C29 | 0.4813 (3) | 0.4972 (2) | 0.02776 (17) | 0.0443 (9) | |
H29 | 0.4127 | 0.5258 | 0.0305 | 0.053* | |
C31 | 0.4748 (3) | 0.4300 (2) | 0.13521 (17) | 0.0431 (9) | |
H31 | 0.3978 | 0.4492 | 0.1319 | 0.052* | |
C32 | 0.5261 (3) | 0.3822 (2) | 0.18814 (16) | 0.0362 (8) | |
H32 | 0.4812 | 0.3690 | 0.2195 | 0.043* | |
C36 | 0.8548 (7) | 0.9101 (5) | 0.0487 (3) | 0.126 (2) | |
H36A | 0.9079 | 0.8675 | 0.0680 | 0.189* | |
H36B | 0.8331 | 0.9024 | 0.0015 | 0.189* | |
H36C | 0.7848 | 0.9087 | 0.0673 | 0.189* | |
C37 | 0.8452 (7) | 1.0606 (5) | 0.0466 (4) | 0.136 (3) | |
H37A | 0.8977 | 1.1066 | 0.0537 | 0.204* | |
H37B | 0.7879 | 1.0653 | 0.0744 | 0.204* | |
H37C | 0.8049 | 1.0590 | 0.0008 | 0.204* | |
C35 | 1.0257 (6) | 0.9922 (5) | 0.0917 (3) | 0.0974 (19) | |
H35 | 1.0679 | 0.9444 | 0.1037 | 0.117* | |
C17 | 0.9963 (5) | 0.0374 (2) | 0.4992 (3) | 0.0875 (17) | |
H17 | 1.0426 | 0.0658 | 0.5343 | 0.105* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni1 | 0.0219 (2) | 0.0209 (2) | 0.0202 (2) | 0.00201 (16) | 0.00443 (15) | 0.00322 (15) |
O1 | 0.0242 (12) | 0.0383 (13) | 0.0317 (12) | −0.0079 (10) | 0.0075 (10) | 0.0012 (10) |
O2 | 0.0452 (16) | 0.0723 (18) | 0.0288 (13) | −0.0189 (14) | 0.0097 (12) | −0.0009 (12) |
O3 | 0.0547 (19) | 0.099 (2) | 0.0357 (15) | −0.0242 (17) | 0.0206 (14) | −0.0117 (15) |
O4 | 0.0575 (18) | 0.0729 (19) | 0.0341 (14) | −0.0282 (15) | 0.0094 (13) | −0.0100 (13) |
O5 | 0.0243 (12) | 0.0225 (12) | 0.0630 (16) | −0.0041 (9) | 0.0016 (11) | −0.0082 (11) |
O7 | 0.0249 (12) | 0.0283 (12) | 0.0329 (12) | 0.0013 (9) | 0.0083 (10) | −0.0022 (9) |
O6 | 0.0377 (15) | 0.0392 (15) | 0.0747 (19) | 0.0058 (11) | 0.0264 (14) | 0.0213 (13) |
O9 | 0.099 (3) | 0.143 (4) | 0.092 (3) | 0.013 (3) | 0.011 (3) | −0.013 (3) |
O8 | 0.0307 (13) | 0.0287 (12) | 0.0329 (12) | 0.0056 (10) | 0.0080 (10) | −0.0005 (9) |
O10 | 0.0521 (17) | 0.0522 (16) | 0.0347 (13) | −0.0039 (13) | 0.0100 (12) | −0.0032 (11) |
O11 | 0.060 (2) | 0.133 (3) | 0.0540 (18) | −0.002 (2) | 0.0183 (16) | −0.0284 (19) |
O12 | 0.079 (3) | 0.132 (3) | 0.072 (2) | 0.008 (2) | 0.032 (2) | −0.001 (2) |
N1 | 0.0264 (14) | 0.0267 (14) | 0.0236 (13) | 0.0004 (11) | 0.0075 (11) | 0.0001 (11) |
N2 | 0.0295 (15) | 0.0265 (14) | 0.0231 (13) | 0.0041 (11) | 0.0042 (11) | 0.0043 (11) |
N3 | 0.0268 (15) | 0.0321 (15) | 0.0303 (14) | 0.0055 (12) | 0.0061 (12) | 0.0091 (11) |
N4 | 0.077 (3) | 0.136 (5) | 0.064 (3) | 0.002 (3) | 0.006 (2) | 0.003 (3) |
C16 | 0.0259 (17) | 0.0236 (17) | 0.0372 (18) | −0.0040 (13) | 0.0051 (15) | −0.0060 (14) |
C15 | 0.0249 (17) | 0.0281 (17) | 0.0364 (17) | −0.0012 (13) | 0.0088 (14) | −0.0039 (14) |
C14 | 0.0311 (19) | 0.0287 (18) | 0.060 (2) | −0.0055 (15) | 0.0093 (17) | −0.0063 (16) |
C13 | 0.025 (2) | 0.044 (2) | 0.078 (3) | −0.0063 (17) | 0.0054 (19) | −0.010 (2) |
C12 | 0.0239 (19) | 0.043 (2) | 0.075 (3) | 0.0031 (16) | 0.0018 (18) | −0.0062 (19) |
C11 | 0.0289 (18) | 0.0260 (17) | 0.062 (2) | 0.0005 (15) | 0.0062 (17) | −0.0075 (16) |
C10 | 0.0240 (17) | 0.0252 (17) | 0.0408 (18) | −0.0022 (13) | 0.0068 (14) | −0.0038 (14) |
C9 | 0.0279 (18) | 0.0249 (17) | 0.0474 (19) | −0.0026 (14) | 0.0072 (15) | −0.0069 (14) |
C8 | 0.0256 (17) | 0.0193 (15) | 0.0390 (18) | −0.0025 (13) | 0.0059 (14) | −0.0038 (13) |
C6 | 0.0316 (18) | 0.0271 (17) | 0.0390 (18) | −0.0060 (14) | 0.0156 (15) | −0.0022 (14) |
C4 | 0.0302 (18) | 0.0293 (17) | 0.0355 (17) | −0.0047 (14) | 0.0080 (15) | −0.0013 (14) |
C5 | 0.044 (2) | 0.044 (2) | 0.0350 (19) | −0.0083 (18) | 0.0110 (17) | −0.0033 (16) |
C3 | 0.0255 (17) | 0.0284 (17) | 0.0328 (17) | −0.0070 (14) | 0.0021 (14) | −0.0018 (13) |
C2 | 0.0245 (16) | 0.0218 (16) | 0.0327 (17) | −0.0007 (13) | 0.0067 (13) | −0.0025 (13) |
C7 | 0.0296 (18) | 0.0234 (16) | 0.0322 (17) | −0.0019 (13) | 0.0053 (14) | −0.0035 (13) |
C1 | 0.0295 (18) | 0.0264 (17) | 0.0302 (17) | −0.0004 (14) | 0.0081 (14) | 0.0011 (13) |
C21 | 0.038 (2) | 0.034 (2) | 0.054 (2) | 0.0056 (16) | 0.0110 (17) | 0.0160 (17) |
C22 | 0.059 (3) | 0.044 (2) | 0.093 (3) | 0.015 (2) | 0.034 (3) | 0.038 (2) |
C18 | 0.042 (2) | 0.095 (3) | 0.059 (3) | 0.030 (2) | 0.014 (2) | 0.045 (2) |
C19 | 0.051 (3) | 0.081 (3) | 0.047 (2) | 0.016 (2) | −0.005 (2) | 0.026 (2) |
C20 | 0.041 (2) | 0.054 (2) | 0.040 (2) | 0.0080 (18) | −0.0019 (17) | 0.0116 (17) |
C26 | 0.0394 (19) | 0.0268 (17) | 0.0280 (16) | 0.0007 (14) | 0.0125 (14) | 0.0013 (13) |
C25 | 0.050 (2) | 0.0244 (17) | 0.0356 (18) | 0.0033 (15) | 0.0149 (16) | 0.0008 (14) |
C24 | 0.0356 (19) | 0.0323 (18) | 0.0294 (17) | 0.0034 (15) | 0.0110 (14) | −0.0014 (14) |
C23 | 0.048 (2) | 0.0318 (18) | 0.0365 (18) | 0.0078 (16) | 0.0161 (16) | −0.0016 (15) |
C28 | 0.043 (2) | 0.0336 (18) | 0.0289 (17) | 0.0000 (15) | 0.0170 (15) | 0.0021 (14) |
C27 | 0.0365 (19) | 0.0252 (16) | 0.0288 (16) | −0.0039 (14) | 0.0092 (14) | 0.0001 (13) |
C33 | 0.0329 (19) | 0.045 (2) | 0.0315 (18) | 0.0044 (16) | 0.0050 (15) | 0.0135 (15) |
C34 | 0.041 (2) | 0.053 (2) | 0.0315 (18) | 0.0008 (17) | 0.0057 (16) | 0.0179 (16) |
C30 | 0.048 (2) | 0.0340 (19) | 0.0313 (18) | 0.0037 (16) | −0.0012 (16) | 0.0092 (15) |
C29 | 0.047 (2) | 0.043 (2) | 0.0374 (19) | 0.0081 (18) | −0.0030 (17) | 0.0133 (17) |
C31 | 0.037 (2) | 0.052 (2) | 0.0389 (19) | 0.0176 (17) | 0.0045 (16) | 0.0130 (17) |
C32 | 0.0350 (19) | 0.044 (2) | 0.0301 (17) | 0.0058 (16) | 0.0072 (15) | 0.0084 (15) |
C36 | 0.134 (6) | 0.152 (7) | 0.092 (5) | −0.029 (5) | 0.027 (4) | −0.004 (5) |
C37 | 0.111 (6) | 0.171 (7) | 0.116 (5) | 0.049 (5) | −0.003 (4) | 0.013 (5) |
C35 | 0.080 (4) | 0.141 (6) | 0.069 (4) | 0.001 (4) | 0.008 (3) | −0.007 (4) |
C17 | 0.082 (3) | 0.093 (4) | 0.095 (3) | 0.029 (3) | 0.037 (3) | 0.048 (3) |
Geometric parameters (Å, º) top
Ni1—O8 | 2.077 (2) | C6—C4 | 1.387 (4) |
Ni1—O7i | 2.077 (2) | C6—H6 | 0.9300 |
Ni1—O1 | 2.086 (2) | C4—C3 | 1.379 (4) |
Ni1—N1 | 2.095 (2) | C4—C5 | 1.495 (5) |
Ni1—N2 | 2.112 (2) | C3—C2 | 1.382 (4) |
Ni1—N3 | 2.123 (3) | C3—H3 | 0.9300 |
O1—C1 | 1.250 (4) | C2—C7 | 1.392 (4) |
O2—C1 | 1.250 (4) | C2—C1 | 1.515 (4) |
O3—C5 | 1.310 (4) | C7—H7 | 0.9300 |
O3—H3A | 0.8200 | C21—C22 | 1.395 (5) |
O4—C5 | 1.208 (4) | C21—H21 | 0.9300 |
O5—C10 | 1.370 (4) | C22—C18 | 1.407 (7) |
O5—C9 | 1.426 (4) | C22—H22 | 0.9300 |
O7—C16 | 1.261 (4) | C18—C19 | 1.353 (7) |
O7—Ni1ii | 2.077 (2) | C18—C17 | 1.494 (6) |
O6—C16 | 1.243 (4) | C19—C20 | 1.337 (5) |
O9—C35 | 1.290 (7) | C19—H19 | 0.9300 |
O8—H8A | 0.8500 | C20—H20 | 0.9300 |
O8—H8B | 0.8500 | C26—C25 | 1.383 (4) |
O10—H10C | 0.8501 | C26—H26 | 0.9300 |
O10—H10A | 0.8498 | C25—C24 | 1.388 (4) |
O11—H11D | 0.8501 | C25—H25 | 0.9300 |
O11—H11A | 0.8500 | C24—C28 | 1.384 (5) |
O12—H12D | 0.8502 | C24—C23 | 1.469 (4) |
O12—H12A | 0.8499 | C23—C23iii | 1.332 (7) |
N1—C26 | 1.335 (4) | C23—H23 | 0.9300 |
N1—C27 | 1.344 (4) | C28—C27 | 1.366 (4) |
N2—C32 | 1.326 (4) | C28—H28 | 0.9300 |
N2—C33 | 1.340 (4) | C27—H27 | 0.9300 |
N3—C20 | 1.329 (4) | C33—C34 | 1.368 (4) |
N3—C21 | 1.332 (4) | C33—H33 | 0.9300 |
N4—C35 | 1.318 (7) | C34—C30 | 1.381 (5) |
N4—C36 | 1.433 (8) | C34—H34 | 0.9300 |
N4—C37 | 1.436 (8) | C30—C31 | 1.387 (5) |
C16—C15 | 1.502 (4) | C30—C29 | 1.474 (4) |
C15—C14 | 1.392 (5) | C29—C29iv | 1.303 (7) |
C15—C10 | 1.394 (4) | C29—H29 | 0.9300 |
C14—C13 | 1.380 (5) | C31—C32 | 1.374 (5) |
C14—H14A | 0.9300 | C31—H31 | 0.9300 |
C13—C12 | 1.370 (5) | C32—H32 | 0.9300 |
C13—H13 | 0.9300 | C36—H36A | 0.9600 |
C12—C11 | 1.381 (5) | C36—H36B | 0.9600 |
C12—H12 | 0.9300 | C36—H36C | 0.9600 |
C11—C10 | 1.388 (5) | C37—H37A | 0.9600 |
C11—H11 | 0.9300 | C37—H37B | 0.9600 |
C9—C8 | 1.501 (4) | C37—H37C | 0.9600 |
C9—H9A | 0.9700 | C35—H35 | 0.9300 |
C9—H9B | 0.9700 | C17—C17v | 1.231 (7) |
C8—C6 | 1.381 (4) | C17—H17 | 0.9300 |
C8—C7 | 1.389 (4) | | |
| | | |
O8—Ni1—O7i | 93.32 (9) | C3—C2—C7 | 118.8 (3) |
O8—Ni1—O1 | 90.86 (9) | C3—C2—C1 | 119.4 (3) |
O7i—Ni1—O1 | 173.48 (8) | C7—C2—C1 | 121.6 (3) |
O8—Ni1—N1 | 177.74 (9) | C8—C7—C2 | 120.8 (3) |
O7i—Ni1—N1 | 88.82 (9) | C8—C7—H7 | 119.6 |
O1—Ni1—N1 | 86.95 (9) | C2—C7—H7 | 119.6 |
O8—Ni1—N2 | 89.38 (9) | O2—C1—O1 | 126.5 (3) |
O7i—Ni1—N2 | 89.02 (9) | O2—C1—C2 | 117.3 (3) |
O1—Ni1—N2 | 96.04 (9) | O1—C1—C2 | 116.2 (3) |
N1—Ni1—N2 | 91.41 (10) | N3—C21—C22 | 122.5 (4) |
O8—Ni1—N3 | 87.94 (9) | N3—C21—H21 | 118.8 |
O7i—Ni1—N3 | 88.29 (9) | C22—C21—H21 | 118.8 |
O1—Ni1—N3 | 86.85 (9) | C21—C22—C18 | 119.2 (4) |
N1—Ni1—N3 | 91.38 (10) | C21—C22—H22 | 120.4 |
N2—Ni1—N3 | 176.09 (10) | C18—C22—H22 | 120.4 |
C1—O1—Ni1 | 146.6 (2) | C19—C18—C22 | 117.2 (4) |
C5—O3—H3A | 109.5 | C19—C18—C17 | 115.7 (5) |
C10—O5—C9 | 116.6 (2) | C22—C18—C17 | 127.1 (5) |
C16—O7—Ni1ii | 128.2 (2) | C20—C19—C18 | 118.7 (4) |
Ni1—O8—H8A | 109.4 | C20—C19—H19 | 120.6 |
Ni1—O8—H8B | 109.3 | C18—C19—H19 | 120.6 |
H8A—O8—H8B | 109.5 | N3—C20—C19 | 127.5 (4) |
H10C—O10—H10A | 109.3 | N3—C20—H20 | 116.3 |
H11D—O11—H11A | 109.8 | C19—C20—H20 | 116.3 |
H12D—O12—H12A | 110.2 | N1—C26—C25 | 123.1 (3) |
C26—N1—C27 | 116.6 (3) | N1—C26—H26 | 118.5 |
C26—N1—Ni1 | 123.4 (2) | C25—C26—H26 | 118.5 |
C27—N1—Ni1 | 119.2 (2) | C26—C25—C24 | 119.8 (3) |
C32—N2—C33 | 116.5 (3) | C26—C25—H25 | 120.1 |
C32—N2—Ni1 | 123.0 (2) | C24—C25—H25 | 120.1 |
C33—N2—Ni1 | 120.4 (2) | C28—C24—C25 | 116.7 (3) |
C20—N3—C21 | 114.9 (3) | C28—C24—C23 | 123.2 (3) |
C20—N3—Ni1 | 123.1 (2) | C25—C24—C23 | 120.1 (3) |
C21—N3—Ni1 | 121.8 (2) | C23iii—C23—C24 | 124.6 (4) |
C35—N4—C36 | 121.3 (7) | C23iii—C23—H23 | 117.7 |
C35—N4—C37 | 119.2 (7) | C24—C23—H23 | 117.7 |
C36—N4—C37 | 119.4 (6) | C27—C28—C24 | 120.1 (3) |
O6—C16—O7 | 124.5 (3) | C27—C28—H28 | 120.0 |
O6—C16—C15 | 117.7 (3) | C24—C28—H28 | 120.0 |
O7—C16—C15 | 117.8 (3) | N1—C27—C28 | 123.6 (3) |
C14—C15—C10 | 118.6 (3) | N1—C27—H27 | 118.2 |
C14—C15—C16 | 118.3 (3) | C28—C27—H27 | 118.2 |
C10—C15—C16 | 123.0 (3) | N2—C33—C34 | 123.4 (3) |
C13—C14—C15 | 121.8 (3) | N2—C33—H33 | 118.3 |
C13—C14—H14A | 119.1 | C34—C33—H33 | 118.3 |
C15—C14—H14A | 119.1 | C33—C34—C30 | 120.2 (3) |
C12—C13—C14 | 118.9 (3) | C33—C34—H34 | 119.9 |
C12—C13—H13 | 120.6 | C30—C34—H34 | 119.9 |
C14—C13—H13 | 120.6 | C34—C30—C31 | 116.2 (3) |
C13—C12—C11 | 120.6 (3) | C34—C30—C29 | 123.3 (3) |
C13—C12—H12 | 119.7 | C31—C30—C29 | 120.5 (3) |
C11—C12—H12 | 119.7 | C29iv—C29—C30 | 125.9 (5) |
C12—C11—C10 | 120.8 (3) | C29iv—C29—H29 | 117.1 |
C12—C11—H11 | 119.6 | C30—C29—H29 | 117.1 |
C10—C11—H11 | 119.6 | C32—C31—C30 | 120.1 (3) |
O5—C10—C11 | 124.0 (3) | C32—C31—H31 | 119.9 |
O5—C10—C15 | 116.7 (3) | C30—C31—H31 | 119.9 |
C11—C10—C15 | 119.3 (3) | N2—C32—C31 | 123.5 (3) |
O5—C9—C8 | 110.0 (3) | N2—C32—H32 | 118.2 |
O5—C9—H9A | 109.7 | C31—C32—H32 | 118.2 |
C8—C9—H9A | 109.7 | N4—C36—H36A | 109.5 |
O5—C9—H9B | 109.7 | N4—C36—H36B | 109.5 |
C8—C9—H9B | 109.7 | H36A—C36—H36B | 109.5 |
H9A—C9—H9B | 108.2 | N4—C36—H36C | 109.5 |
C6—C8—C7 | 119.1 (3) | H36A—C36—H36C | 109.5 |
C6—C8—C9 | 119.6 (3) | H36B—C36—H36C | 109.5 |
C7—C8—C9 | 121.1 (3) | N4—C37—H37A | 109.5 |
C8—C6—C4 | 120.9 (3) | N4—C37—H37B | 109.5 |
C8—C6—H6 | 119.5 | H37A—C37—H37B | 109.5 |
C4—C6—H6 | 119.5 | N4—C37—H37C | 109.5 |
C3—C4—C6 | 119.1 (3) | H37A—C37—H37C | 109.5 |
C3—C4—C5 | 118.2 (3) | H37B—C37—H37C | 109.5 |
C6—C4—C5 | 122.5 (3) | O9—C35—N4 | 122.6 (7) |
O4—C5—O3 | 123.9 (3) | O9—C35—H35 | 118.7 |
O4—C5—C4 | 122.5 (3) | N4—C35—H35 | 118.7 |
O3—C5—C4 | 113.6 (3) | C17v—C17—C18 | 126.0 (8) |
C4—C3—C2 | 121.3 (3) | C17v—C17—H17 | 117.0 |
C4—C3—H3 | 119.4 | C18—C17—H17 | 117.0 |
C2—C3—H3 | 119.4 | | |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y+1, −z; (v) −x+2, −y, −z+1. |
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