Abstract
C16H20N4NiO14, orthorhombic, Pnma (No. 62), a = 7.1945(2) Å, b = 16.1805(4) Å, c = 17.7912(5) Å, V = 2071.08(10) Å3, Z = 4, Rgt(F) = 0.0353, wRref(F2) = 0.0997, T = 293(2) K.
The title complex is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Data collection and handling.
Crystal: | Blue block |
Size: | 0.21 × 0.19 × 0.15 mm |
Wavelength: | Mo Kα radiation (0.71073 Å) |
μ: | 1.02 mm−1 |
Diffractometer, scan mode: | Bruker D8 VENTURE PHOTON, φ and ω |
θmax, completeness: | 27.5°, >99% |
N(hkl)measured, N(hkl)unique, Rint: | 19,289, 2457, 0.044 |
Criterion for Iobs, N(hkl)gt: | Iobs > 2σ(Iobs), 2071 |
N(param)refined: | 173 |
Programs: | SHELX [1], Bruker [2, 3] |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).
Atom | x | y | z | Uiso*/Ueq |
---|---|---|---|---|
Ni1 | 0.85106 (6) | 0.750000 | −0.02377 (2) | 0.02858 (14) |
O1 | 0.8891 (3) | 0.64733 (10) | −0.09459 (9) | 0.0380 (4) |
O2 | 0.8422 (3) | 0.51153 (10) | −0.09723 (9) | 0.0417 (4) |
O3 | 0.7149 (3) | 0.40744 (10) | −0.01041 (10) | 0.0411 (4) |
H3 | 0.761797 | 0.443422 | −0.036739 | 0.062* |
O4 | 0.5869 (3) | 0.40029 (10) | 0.10246 (10) | 0.0462 (5) |
O5 | 0.5726 (4) | 0.750000 | −0.05902 (15) | 0.0439 (6) |
H5 | 0.525959 | 0.789800 | −0.083862 | 0.066* |
O6 | 1.1317 (4) | 0.750000 | −0.00514 (17) | 0.0472 (6) |
H6 | 1.190801 | 0.795420 | −0.007356 | 0.071* |
O7 | 0.5062 (3) | 0.49183 (12) | 0.24964 (10) | 0.0512 (5) |
H7A | 0.568851 | 0.484683 | 0.289612 | 0.077* |
H7B | 0.477481 | 0.441742 | 0.241101 | 0.077* |
N1 | 0.7931 (3) | 0.65986 (11) | 0.05063 (10) | 0.0276 (4) |
N2 | 0.6759 (3) | 0.56915 (11) | 0.12886 (10) | 0.0288 (4) |
H2 | 0.629388 | 0.548025 | 0.169032 | 0.035* |
C1 | 0.8400 (3) | 0.58154 (14) | −0.06440 (13) | 0.0316 (5) |
C2 | 0.7783 (3) | 0.58545 (13) | 0.01493 (12) | 0.0283 (4) |
C3 | 0.7058 (3) | 0.52823 (13) | 0.06308 (12) | 0.0286 (4) |
C4 | 0.6643 (3) | 0.43920 (14) | 0.05327 (14) | 0.0328 (5) |
C5 | 0.7319 (3) | 0.64909 (13) | 0.12055 (12) | 0.0272 (4) |
C6 | 0.7391 (3) | 0.70621 (13) | 0.18527 (11) | 0.0270 (4) |
C7 | 0.7506 (3) | 0.66589 (14) | 0.25481 (12) | 0.0350 (5) |
H7 | 0.755439 | 0.608457 | 0.255346 | 0.042* |
C8 | 0.7550 (4) | 0.70717 (15) | 0.32219 (12) | 0.0381 (5) |
H8 | 0.757917 | 0.678048 | 0.367237 | 0.046* |
O8a | 0.451 (3) | 0.3117 (7) | 0.2578 (7) | 0.252 (10) |
O8′a | 0.3126 (16) | 0.3409 (5) | 0.2470 (6) | 0.129 (3) |
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aOccupancy: 0.5.
Source of material
The reagents used in this paper are purchased from commercial sources without further purification. An aqueous solution (2 mL) of NiCl2·4H2O (0.02 mmol) was added dropwise to a methanol solution (2 mL) of 2,2′-(1,2-phenylene)bis(1H-imidazole-4,5-dicarboxylic acid) (H6Phbidc, 0.02 mmol). A clear solution was obtained after filtration and placed in a closed container at room temperature. Light blue crystals can be obtained after four weeks (yield 51%, based H6Phbidc).
Experimental details
Hydrogen atoms bound to C and N atoms were positioned geometrically and refined as riding atoms, with C–H = 0.93 Å and N–H = 0.86 Å. H atoms of the nondeprotonated carboxylic acid groups were refined as riding atoms, with O–H = 0.82 Å. H atoms on O5, O6, O7 were found according to the residual electron-density peaks around each water O atom and the directions of hydrogen bonds, and were then locked in position and included with O–H = 0.85 Å. All H atoms were refined with Uiso(H) = 1.2 Ueq(C, N) and 1.5 UeqO. One guest water molecule (O8) is disordered and the hydrogen atoms of this water molecule could not be located in the difference Fourier map.
Comment
1H-Imidazole-4,5-dicarboxylic acid and its derivatives, such as 2-(hydroxymethyl)-1H-imidazole-4,5-dicarboxylic acid, 2-(pyridin-4-yl)-1H-imidazole-4,5-dicarboxylic acid, 2,2′-(1,2-phenylene)bis(1H-imidazole-4,5-dicarboxylic acid), 2-phenyl-1H-imidazole-4,5-dicarboxylic acid, 2-(1H-tetrazol-1-yl)-1H-imidazole-4,5-dicarboxylic acid, 2,2′-(ethane-1,2-diyl)bis(1H-imidazole-4,5-dicarboxylic acid), are good linkers and have been widely used in the synthesis of new coordination complexes (CPs) since they contain not only N-donors but also O-donors, which have abundant coordination modes and can lead to CPs with various structures and interesting properties [4], [5], [6], [7], [8], [9], [10], [11], [12]. Among the reported ligands, 2,2′-(1,2-phenylene)bis(1H-imidazole-4,5-dicarboxylic acid) (H6Phbidc), and corresponding deprotonated anions are excellent ligands as there are four potential N-donors and eight potential O-donors and can coordinate to almost all soft and hard metal ions with various coordination modes. Up to now, only a small number of CPs based on H6Phbidc have been reported [8, 13, 14]. In order to further enrich the categories and numbers of CPs based on this ligand, we synthesized the title compound.
The asymmetric unit of the title structure consists of one half of Ni(II) ion, one half of 2,2′-(1,2-phenylene)bis(1H-imidazole-4,5-dicarboxylate anion (H4Phbidc2−), two halfs of coordination water molecules and two uncoordinated water molecules. Each Ni1 ion is six-coordinated and located in a distorted octahedral NiN2O4 coordination environment formed by two N atoms (N1 and N1#1) and two O atoms (O1 and O1#1) from one H4Phbidc2− anion and by two water molecules (O5 and O6). The Ni–N bond lengths is 2.0133(18) Å and the Ni–O bond lengths are 2.046(3), 2.099(3), 2.1028(16) and 2.1029(16) Å, respectively; these values are within the normal ranges and close to those reported in other Ni(II) complexes [15], [16], [17]. The bond angles of O6–Ni1–O5, N1–Ni1–O1#1 and N1#1–Ni1–O1 are 171.94(12)°, 173.30(7)° and 173.30(7)°, respectively. The other bond angles around the Ni1 ion are more or less deviated from the ideal values (81.29(7)°–95.63(8)°). There are O–H⋯O intramolecular hydrogen bonds between carboxyl and carboxylate groups, N–H⋯O intermolecular hydrogen bonds between imidazole units and solvent water molecules and O–H⋯O intermolecular hydrogen bonds involving coordination water molecules, solvent water molecules and carboxylate groups. Furthermore, there are π–π stacking interactions between C6/C7/C8/C6#1/C7#1/C8#1 benzene rings with a centroid-centroid distance of 3.6002(1) Å, which are in the range for common π-π interactions [9, 18, 19]. [Ni(H4Phbidc)(H2O)2] molecules are linked by the above hydrogen bonds and π–π interactions, resulting in a three-dimensional supramolecular architecture in the solid state.
Funding source: National Natural Science Foundation
Award Identifier / Grant number: 202010459001
Acknowledgements
This work was financially supported by the National Natural Science Foundation (no. 202010459001).
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Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
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Research funding: National Natural Science Foundation (no. 202010459001).
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Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
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© 2021 Xu Liu and Xiang-Ru Meng, published by De Gruyter, Berlin/Boston
This work is licensed under the Creative Commons Attribution 4.0 International License.
Artikel in diesem Heft
- Frontmatter
- New Crystal Structures
- Crystal structure of {2,2′-{cyclohexane-1,2-diylbis[(azanylylidene)methylylidene]}bis(2,4-dibromophenolato)-κ4 N,N′,O,O′}copper(II) ─ diethylformamide (1/1), C23H23Br4CuN3O3
- The crystal structure of 2-(2-methyl-6-phenyl-4H-pyran-4-ylidene)-1H-indene-1,3(2H)-dione, C21H14O3
- Crystal structure of bis((1-methylbenzimidazol-2-yl)methyl)amine, C18H19N5
- Crystal structure of (E)-N′-(1-(2-hydroxy-4-methoxyphenyl)ethylidene) isonicotinohydrazide, C15H15N3O3
- Crystal structure of 2-((4-phenyl-5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl)thio)acetonitrile, C15H11N5S
- The crystal structure of 2,2′-((1E,1′E)-hydrazine-1,2-diylidenebis(methaneylylidene))bis(4-chlorophenol), C14H10Cl2N2O2
- Dichlorido-{2,6-bis(4,5-dihydro-1H-pyrazol-3-yl)pyridine-κ3 N,N′,N″}zinc(II), C11H9C12N5Zn
- The crystal structure of dichlorido-(2-((4-phenyl-2H-1,2,3-triazol-2-yl)methyl)pyridine-κ2N,N′)palladium(II), C14H12Cl2N4Pd
- The crystal structure of 1-(N1-benzyl-2-methyl-4-nitro-imidazol-5-yl)-4-(prop-2-yn-1-yl) piperazine, C18H21N5O2
- Crystal structure of (μ4-(1,2,4,5-tetra(1,2,4-triazol-1-ylmethyl)-benzene-κ4N:N1:N2:N3)disilver(I) diperchlorate
- The crystal structure of 1-(2-bromoethane)-4-amine-3,5-dinitropyrazole, C5H6Br1N5O4
- Crystal structure of (E)-1-(4-benzyl-3,5-dioxomorpholin-2-ylidene)ethyl acetate, C15H15N1O5
- The crystal structure of poly[diaqua-(μ2-1,2,4,5-tetrakis(1,2,4-triazol-1-ylmethyl)-benzene-κ2N:N′)-bis(μ3-terephthalato-κ3O:O′:O′′)dicadmium(II)], C17H15N6O5Cd
- Crystal structure of (E)-N′-(1-(5-chloro-2-hydroxyphenyl) ethylidene)thiophene-2-carbohydrazide, C13H11ClN2O2S
- The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylato-k2 N,O)cobalt(II)]-monohydrate, C36H26N4O5Co
- Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-3-hydroxybenzo-hydrazide monohydrate, C14H13ClN2O4
- Crystal structure of 1,1′-(methylene)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2S:S)nickel(II), C42H30N14Ni2S8
- Crystal structure of 1,1′-(1,2-ethanediyl)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2 S:S)nickel(II), C20H14N6NiS4
- The crystal structure of 1-methyl-1H-pyrazol-2-ium nitrate, C4H7O3N3
- The crystal structure of 4,4′-diselanediylbis(8-(hexyloxy)-3,6-dimethyl-1-(piperidin-1-yl)isoquinoline-7-carbonitrile), C46H60N6O2Se2
- The crystal structure of tris(6-methylpyridin-2-yl)phosphine selenide, C18H18N3PSe
- The crystal structure of 1,2-bis(2,4-dinitro-1H-imidazol-1-yl)ethane ─ acetone (1/1), C11H12N8O9
- Crystal structure of [diaqua[2,2′-(1,2-phenylene)bis(1H-imidazole-4-carboxylato-5-carboxy)-κ4N,N′,O,O′]nickel(II)] tetrahydrate, C16H12N4NiO10·4H2O
- The crystal structure of tris(4-methyl-1H-pyrazol-1-yl)methane, C13H16N6
- The crystal structure of 5,6-dichloro-2-(quinolin-8-yl)isoindoline-1,3-dione, C17H8Cl2N2O2
- Crystal structure of (E)-(2-methoxy-benzylidene)-(4-[1,2,4]triazol-1-yl-phenyl)-amine, C16H14N4O
- The crystal structure of (Z)-2-(4-(4-bromophenyl)thiazol-2-yl)-4-(3-hydroxybut-2-enoyl)-5-methyl -1,2-dihydro-3H-pyrazol-3-one – methanol (1/1), C18H18N3O4S
- Crystal structure of tetraaqua-tris(nitrato-κ2 O,O′) erbium(III) monohydrate, Er(NO3)3·5H2O, H10ErN3O14
- The crystal structure of 1-methyl-2-nitro-1H-imidazole 3-oxide, C4H5N3O3
- The crystal structure of 1-methyl-2-nitroimidazole, C4H5N3O2
- The crystal structure of 2-carboxyl-4-nitroimidazole monohydrate, C4H5N3O5
- Crystal structure of bis[hydrido-hexaphenylcarbodiphosphoran][tetra-trifluoromethyl-(μ-diiodo)-diplatinat]
- The crystal structure of poly[μ2-aqua- aqua-(μ3-(E)-2-(4-((2-carbamothioylhydrazineylidene)methyl)phenoxy)acetato-κ3 O:S:S)sodium(I)], C10H14N3O5SNa
- The twinned crystal structure of [4,4′-bipyridine]-1,1′-diium hexachloridostannate(IV), C10H10N2SnCl6
- The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylate-k2 N,O)copper(II)], C34H24N4O4Cu
- Crystal structure of trans-1,2-bis(pyridinium-4-yl) ethylene bis(2-carboxy-4-bromobenzoate) – water (1/4), C14H14BrNO6
- Crystal structure of poly[diaqua-(μ3-fumarato)-(μ3-maleato)-(μ4-1,2,4,5-tetrakis((1H-1,2,4-triazol-1-yl)methyl)benzene)tetracadmium(II)] dihydrate, C34H32N12O9Cd4
- Crystal structure of a second modification of Pachypodol, C18H16O7
- Crystal structure of methyl 2-(4-(2-(cyclopentyl-amino)-1-(N-(4-methoxyphenyl)-1-methyl-5-phenyl-1-H-pyrazole-3-carboxamido)-2-oxoethyl)phenyl)acetate, C34H36N4O5
- The crystal structure of catena-poly[(m2-4,4′-bipyridine-κ2 N:N)-bis(6-phenylpyridine-2-carboxylato-κ2 N,O) zinc(II)], C34H24N4O4Zn
- The crystal structure of hexaquamagnesium(II) (2,4-bis(nitroimino)-6-oxo-1,3,5-triazinane-1,3-diide), C3H15MgN7O12
- The crystal structure of 7-Bromo-2-(4-chloro-phenyl)-quinoxaline, C14H9BrClN2
- Crystal structure of methyl 4-{[4-(4-cyanobenzamido)phenyl]amino}benzofuro[2,3-d]pyrimidine-6-carboxylate, C26H17N5O4
- The crystal structure of (4SR)-7-(3,4-dichlorobenzyl)-4,8,8-trimethyl-7,8-dihydroimidazo[5,1c][1,2,4]triazine-3,6(2H,4H)-dione, C15H16Cl2N4O2
- Crystal structure of catena-poly[{μ2-3-carboxy-2,3-bis((4-methylbenzoyl)oxy)propanoato-κ2 O:O′}tris(methanol-κ1 O)lanthanum(III)], C63H63LaO27
Artikel in diesem Heft
- Frontmatter
- New Crystal Structures
- Crystal structure of {2,2′-{cyclohexane-1,2-diylbis[(azanylylidene)methylylidene]}bis(2,4-dibromophenolato)-κ4 N,N′,O,O′}copper(II) ─ diethylformamide (1/1), C23H23Br4CuN3O3
- The crystal structure of 2-(2-methyl-6-phenyl-4H-pyran-4-ylidene)-1H-indene-1,3(2H)-dione, C21H14O3
- Crystal structure of bis((1-methylbenzimidazol-2-yl)methyl)amine, C18H19N5
- Crystal structure of (E)-N′-(1-(2-hydroxy-4-methoxyphenyl)ethylidene) isonicotinohydrazide, C15H15N3O3
- Crystal structure of 2-((4-phenyl-5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl)thio)acetonitrile, C15H11N5S
- The crystal structure of 2,2′-((1E,1′E)-hydrazine-1,2-diylidenebis(methaneylylidene))bis(4-chlorophenol), C14H10Cl2N2O2
- Dichlorido-{2,6-bis(4,5-dihydro-1H-pyrazol-3-yl)pyridine-κ3 N,N′,N″}zinc(II), C11H9C12N5Zn
- The crystal structure of dichlorido-(2-((4-phenyl-2H-1,2,3-triazol-2-yl)methyl)pyridine-κ2N,N′)palladium(II), C14H12Cl2N4Pd
- The crystal structure of 1-(N1-benzyl-2-methyl-4-nitro-imidazol-5-yl)-4-(prop-2-yn-1-yl) piperazine, C18H21N5O2
- Crystal structure of (μ4-(1,2,4,5-tetra(1,2,4-triazol-1-ylmethyl)-benzene-κ4N:N1:N2:N3)disilver(I) diperchlorate
- The crystal structure of 1-(2-bromoethane)-4-amine-3,5-dinitropyrazole, C5H6Br1N5O4
- Crystal structure of (E)-1-(4-benzyl-3,5-dioxomorpholin-2-ylidene)ethyl acetate, C15H15N1O5
- The crystal structure of poly[diaqua-(μ2-1,2,4,5-tetrakis(1,2,4-triazol-1-ylmethyl)-benzene-κ2N:N′)-bis(μ3-terephthalato-κ3O:O′:O′′)dicadmium(II)], C17H15N6O5Cd
- Crystal structure of (E)-N′-(1-(5-chloro-2-hydroxyphenyl) ethylidene)thiophene-2-carbohydrazide, C13H11ClN2O2S
- The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylato-k2 N,O)cobalt(II)]-monohydrate, C36H26N4O5Co
- Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-3-hydroxybenzo-hydrazide monohydrate, C14H13ClN2O4
- Crystal structure of 1,1′-(methylene)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2S:S)nickel(II), C42H30N14Ni2S8
- Crystal structure of 1,1′-(1,2-ethanediyl)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2 S:S)nickel(II), C20H14N6NiS4
- The crystal structure of 1-methyl-1H-pyrazol-2-ium nitrate, C4H7O3N3
- The crystal structure of 4,4′-diselanediylbis(8-(hexyloxy)-3,6-dimethyl-1-(piperidin-1-yl)isoquinoline-7-carbonitrile), C46H60N6O2Se2
- The crystal structure of tris(6-methylpyridin-2-yl)phosphine selenide, C18H18N3PSe
- The crystal structure of 1,2-bis(2,4-dinitro-1H-imidazol-1-yl)ethane ─ acetone (1/1), C11H12N8O9
- Crystal structure of [diaqua[2,2′-(1,2-phenylene)bis(1H-imidazole-4-carboxylato-5-carboxy)-κ4N,N′,O,O′]nickel(II)] tetrahydrate, C16H12N4NiO10·4H2O
- The crystal structure of tris(4-methyl-1H-pyrazol-1-yl)methane, C13H16N6
- The crystal structure of 5,6-dichloro-2-(quinolin-8-yl)isoindoline-1,3-dione, C17H8Cl2N2O2
- Crystal structure of (E)-(2-methoxy-benzylidene)-(4-[1,2,4]triazol-1-yl-phenyl)-amine, C16H14N4O
- The crystal structure of (Z)-2-(4-(4-bromophenyl)thiazol-2-yl)-4-(3-hydroxybut-2-enoyl)-5-methyl -1,2-dihydro-3H-pyrazol-3-one – methanol (1/1), C18H18N3O4S
- Crystal structure of tetraaqua-tris(nitrato-κ2 O,O′) erbium(III) monohydrate, Er(NO3)3·5H2O, H10ErN3O14
- The crystal structure of 1-methyl-2-nitro-1H-imidazole 3-oxide, C4H5N3O3
- The crystal structure of 1-methyl-2-nitroimidazole, C4H5N3O2
- The crystal structure of 2-carboxyl-4-nitroimidazole monohydrate, C4H5N3O5
- Crystal structure of bis[hydrido-hexaphenylcarbodiphosphoran][tetra-trifluoromethyl-(μ-diiodo)-diplatinat]
- The crystal structure of poly[μ2-aqua- aqua-(μ3-(E)-2-(4-((2-carbamothioylhydrazineylidene)methyl)phenoxy)acetato-κ3 O:S:S)sodium(I)], C10H14N3O5SNa
- The twinned crystal structure of [4,4′-bipyridine]-1,1′-diium hexachloridostannate(IV), C10H10N2SnCl6
- The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylate-k2 N,O)copper(II)], C34H24N4O4Cu
- Crystal structure of trans-1,2-bis(pyridinium-4-yl) ethylene bis(2-carboxy-4-bromobenzoate) – water (1/4), C14H14BrNO6
- Crystal structure of poly[diaqua-(μ3-fumarato)-(μ3-maleato)-(μ4-1,2,4,5-tetrakis((1H-1,2,4-triazol-1-yl)methyl)benzene)tetracadmium(II)] dihydrate, C34H32N12O9Cd4
- Crystal structure of a second modification of Pachypodol, C18H16O7
- Crystal structure of methyl 2-(4-(2-(cyclopentyl-amino)-1-(N-(4-methoxyphenyl)-1-methyl-5-phenyl-1-H-pyrazole-3-carboxamido)-2-oxoethyl)phenyl)acetate, C34H36N4O5
- The crystal structure of catena-poly[(m2-4,4′-bipyridine-κ2 N:N)-bis(6-phenylpyridine-2-carboxylato-κ2 N,O) zinc(II)], C34H24N4O4Zn
- The crystal structure of hexaquamagnesium(II) (2,4-bis(nitroimino)-6-oxo-1,3,5-triazinane-1,3-diide), C3H15MgN7O12
- The crystal structure of 7-Bromo-2-(4-chloro-phenyl)-quinoxaline, C14H9BrClN2
- Crystal structure of methyl 4-{[4-(4-cyanobenzamido)phenyl]amino}benzofuro[2,3-d]pyrimidine-6-carboxylate, C26H17N5O4
- The crystal structure of (4SR)-7-(3,4-dichlorobenzyl)-4,8,8-trimethyl-7,8-dihydroimidazo[5,1c][1,2,4]triazine-3,6(2H,4H)-dione, C15H16Cl2N4O2
- Crystal structure of catena-poly[{μ2-3-carboxy-2,3-bis((4-methylbenzoyl)oxy)propanoato-κ2 O:O′}tris(methanol-κ1 O)lanthanum(III)], C63H63LaO27