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Crystal structure of bis((1-methylbenzimidazol-2-yl)methyl)amine, C18H19N5

  • Meng Gaoxiang ORCID logo EMAIL logo , Yongming Yang , Qiang Li and Zhou Li
Published/Copyright: January 4, 2022
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 237 Issue 2

Abstract

C18H19N5, triclinic, P 1 ‾ (no. 2), a = 6.612(4) Å, b = 8.800(5) Å, c = 13.777(8) Å, α = 83.219(7)°, β = 79.329(6)°, γ = 78.744(6)°, V = 769.8(8) Å3, Z = 2, R gt (F) = 0.0394, wR ref (F 2) = 0.0996, T = 100(2) K.

CCDC no.: 2120269

The molecular structure 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.

Table 1:

Data collection and handling.

Crystal: Colorless block
Size: 0.12 × 0.10 × 0.06 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.08 mm−1
Diffractometer, scan mode: Bruker Apex II, φ and ω
θ max, completeness: 26.9°, >99%
N(hkl)measured, N(hkl)unique, R int: 8564, 3284, 0.028
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 2882
N(param)refined: 213
Programs: Bruker [1], SHELX [2], [3], [4], Diamond [5], Olex2 [6]
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

Atom x y z U iso*/U eq
C1 0.6990 (2) 0.87744 (15) 0.38431 (9) 0.0231 (3)
H1A 0.750452 0.809345 0.329364 0.028*
H1B 0.545026 0.905601 0.390128 0.028*
C2 0.7522 (2) 0.78962 (15) 0.47868 (9) 0.0205 (3)
C3 0.9439 (2) 0.65481 (14) 0.58565 (9) 0.0209 (3)
C4 1.0994 (2) 0.57547 (15) 0.63811 (10) 0.0254 (3)
H4 1.243623 0.572320 0.612476 0.030*
C5 1.0325 (2) 0.50132 (16) 0.72976 (10) 0.0283 (3)
H5 1.133474 0.445801 0.767920 0.034*
C6 0.8193 (2) 0.50651 (15) 0.76730 (10) 0.0282 (3)
H6 0.778991 0.454756 0.830416 0.034*
C7 0.6660 (2) 0.58549 (15) 0.71432 (10) 0.0265 (3)
H7 0.521838 0.588559 0.740195 0.032*
C8 0.7301 (2) 0.66057 (14) 0.62154 (9) 0.0215 (3)
C9 1.1454 (2) 0.76232 (17) 0.42700 (10) 0.0272 (3)
H9A 1.131995 0.748151 0.359115 0.041*
H9B 1.263540 0.686814 0.446856 0.041*
H9C 1.169421 0.867948 0.430006 0.041*
C10 0.76723 (19) 1.08687 (14) 0.25882 (9) 0.0199 (3)
H10A 0.810416 1.189947 0.247988 0.024*
H10B 0.618511 1.102050 0.251113 0.024*
C11 0.89728 (19) 0.98427 (14) 0.18280 (9) 0.0179 (3)
C12 0.99944 (19) 0.82134 (14) 0.07210 (9) 0.0184 (3)
C13 1.0174 (2) 0.71265 (15) 0.00300 (9) 0.0230 (3)
H13 0.897240 0.680915 −0.011022 0.028*
C14 1.2158 (2) 0.65314 (15) −0.04409 (10) 0.0253 (3)
H14 1.231487 0.579007 −0.091015 0.030*
C15 1.3946 (2) 0.69955 (15) −0.02430 (10) 0.0250 (3)
H15 1.528120 0.656249 −0.058367 0.030*
C16 1.3814 (2) 0.80672 (15) 0.04355 (9) 0.0227 (3)
H16 1.501975 0.838268 0.057207 0.027*
C17 1.18051 (19) 0.86563 (14) 0.09066 (9) 0.0183 (3)
C18 1.2411 (2) 1.05296 (17) 0.20302 (11) 0.0275 (3)
H18A 1.243686 1.154931 0.166004 0.041*
H18B 1.383646 0.993132 0.197540 0.041*
H18C 1.183862 1.066871 0.272921 0.041*
N1 0.78974 (17) 1.01903 (13) 0.36043 (8) 0.0210 (2)
H1 0.713 (2) 1.0893 (19) 0.4025 (12) 0.025*
N2 0.95392 (16) 0.73860 (12) 0.49388 (8) 0.0208 (2)
N3 0.61208 (17) 0.74629 (13) 0.55304 (8) 0.0231 (2)
N4 1.11084 (16) 0.96983 (12) 0.16239 (8) 0.0190 (2)
N5 0.82334 (16) 0.89714 (12) 0.13125 (8) 0.0196 (2)

Source of material

All the reagents and solvents were used as obtained without further purification. Bis((1-methylbenzimidazol-2-yl)methyl)amine (MeIDB) was prepared according to a slightly modified method described by Adams et al. [7] in which only the raw material o-phenylenediamine was changed to be N,N′-dimethyl-1,2-phenylenediamine. Crystals of MeIDB were obtained three days later by slow evaporation in methanol (95%) at room temperature.

Experimental details

Hydrogen atoms bonded to carbon atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms with C–H = 0.95 Å (aromatic), 0.99 Å (methylene), 0.98 Å (methyl) U iso(H) = 1.2U eq (aromatic and methylene) and 1.5U eq (methyl). The H atom at N1 was found from the difference maps, which was refined freely and the U iso value set to 1.2 times of U eq(N1).

Comment

Multi-benzimidazole ligands have been often used in the synthesis of various metal-organic complexes or modelling the biomimetic coordination environment around the enzymatic active site [7]. For instance, by employing a tripodal bis(benzimidazole) ligand bis((1-methylbenzimidazol-2-yl)methyl)amine(MeIDB) and its derivative as the main ligand, a series of nickel and copper complexes were synthesized which allow a systematic investigation of a biomimetic chemistry [8, 9]. However, up to now the detailed crystallization properties of MeIDB has been not reported which can be helpful for the design of various multifunctional compounds due to its central acyclic –CH2–N–CH2– linkage moiety, making the ligand possess various steric arrangements. We have also synthesized some complexes involving tetrazole ligands, to get fluorescent materials [10, 11].

The titled compound was crystallized as one anhydrous form in the triclinic P 1 ‾ space group with only one MeIDB molecule in its asymmetric unit. The MeIDB molecule adopts a nearly V-shaped conformation which is reflected by the torsion angle of –C2–C1–N1–C10– (169.6(1)°), –C1–N1–C10–C11 (−67.3(1)°) and the dihedral angle between two benzimidazole groups (74.4(1)°) which is apparently distinct from most of its analogs [7]. The single bonds C2–N2 and C11–N4 are respectively about 0.05 Å longer than the neighboring C2–N3 and C11–N5 double bonds, indicating their potentially donating electron ability.

In the crystal packing, the MeIDB molecules are linked mainly by a: one N1–H1⃛N3 hydrogen bond (d N1⃛N3 = 3.164(1) Å), 146.4(1)°, symmetry code: 1−x, 2−y, 1−z); b: one π⃛π stacking between imidazole group (N4/N5/C11/C12/C17) and the symmetry related benzene rings (C12–C17, symmetry code: 2−x, 2−y, −z) with a centroid-to-centroid distance of 3.569(2) Å; c: one C–H⃛π interaction (C6–H6⃛Cg (Cg is the centroid of phenyl C12–C17, symmetry code: 2−x, 1−y, 1−z) connecting molecules into a two-dimensional network parallel to the [111] plane. There are no specific directional intermolecular interactions between these adjacent two dimensional layers PLATON [12]. Finally it should be mentioned that the title molecule has been used as a ligand [13].

Corresponding author: Meng Gaoxiang, School of Advanced Materials and Mechatronic Engineering, Hubei Minzu University , Enshi 445000, Hubei, P. R. China, E-mail:

Funding source: Hubei Minzu University Null

Award Identifier / Grant number: PY21016

Award Identifier / Grant number: PY21016

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: This work is supported by High Level Scientific Research Achievements In-school Cultivation Project of Hubei Minzu University (PY21016).

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Received: 2021-11-04
Accepted: 2021-12-14
Published Online: 2022-01-04
Published in Print: 2022-04-26

© 2021 Meng Gaoxiang et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. 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
  4. The crystal structure of 2-(2-methyl-6-phenyl-4H-pyran-4-ylidene)-1H-indene-1,3(2H)-dione, C21H14O3
  5. Crystal structure of bis((1-methylbenzimidazol-2-yl)methyl)amine, C18H19N5
  6. Crystal structure of (E)-N′-(1-(2-hydroxy-4-methoxyphenyl)ethylidene) isonicotinohydrazide, C15H15N3O3
  7. Crystal structure of 2-((4-phenyl-5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl)thio)acetonitrile, C15H11N5S
  8. The crystal structure of 2,2′-((1E,1′E)-hydrazine-1,2-diylidenebis(methaneylylidene))bis(4-chlorophenol), C14H10Cl2N2O2
  9. Dichlorido-{2,6-bis(4,5-dihydro-1H-pyrazol-3-yl)pyridine-κ3 N,N′,N″}zinc(II), C11H9C12N5Zn
  10. The crystal structure of dichlorido-(2-((4-phenyl-2H-1,2,3-triazol-2-yl)methyl)pyridine-κ2N,N′)palladium(II), C14H12Cl2N4Pd
  11. The crystal structure of 1-(N1-benzyl-2-methyl-4-nitro-imidazol-5-yl)-4-(prop-2-yn-1-yl) piperazine, C18H21N5O2
  12. Crystal structure of (μ4-(1,2,4,5-tetra(1,2,4-triazol-1-ylmethyl)-benzene-κ4N:N1:N2:N3)disilver(I) diperchlorate
  13. The crystal structure of 1-(2-bromoethane)-4-amine-3,5-dinitropyrazole, C5H6Br1N5O4
  14. Crystal structure of (E)-1-(4-benzyl-3,5-dioxomorpholin-2-ylidene)ethyl acetate, C15H15N1O5
  15. 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
  16. Crystal structure of (E)-N′-(1-(5-chloro-2-hydroxyphenyl) ethylidene)thiophene-2-carbohydrazide, C13H11ClN2O2S
  17. The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylato-k2 N,O)cobalt(II)]-monohydrate, C36H26N4O5Co
  18. Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-3-hydroxybenzo-hydrazide monohydrate, C14H13ClN2O4
  19. Crystal structure of 1,1′-(methylene)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2S:S)nickel(II), C42H30N14Ni2S8
  20. 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
  21. The crystal structure of 1-methyl-1H-pyrazol-2-ium nitrate, C4H7O3N3
  22. The crystal structure of 4,4′-diselanediylbis(8-(hexyloxy)-3,6-dimethyl-1-(piperidin-1-yl)isoquinoline-7-carbonitrile), C46H60N6O2Se2
  23. The crystal structure of tris(6-methylpyridin-2-yl)phosphine selenide, C18H18N3PSe
  24. The crystal structure of 1,2-bis(2,4-dinitro-1H-imidazol-1-yl)ethane ─ acetone (1/1), C11H12N8O9
  25. 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
  26. The crystal structure of tris(4-methyl-1H-pyrazol-1-yl)methane, C13H16N6
  27. The crystal structure of 5,6-dichloro-2-(quinolin-8-yl)isoindoline-1,3-dione, C17H8Cl2N2O2
  28. Crystal structure of (E)-(2-methoxy-benzylidene)-(4-[1,2,4]triazol-1-yl-phenyl)-amine, C16H14N4O
  29. 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
  30. Crystal structure of tetraaqua-tris(nitrato-κ2 O,O′) erbium(III) monohydrate, Er(NO3)3·5H2O, H10ErN3O14
  31. The crystal structure of 1-methyl-2-nitro-1H-imidazole 3-oxide, C4H5N3O3
  32. The crystal structure of 1-methyl-2-nitroimidazole, C4H5N3O2
  33. The crystal structure of 2-carboxyl-4-nitroimidazole monohydrate, C4H5N3O5
  34. Crystal structure of bis[hydrido-hexaphenylcarbodiphosphoran][tetra-trifluoromethyl-(μ-diiodo)-diplatinat]
  35. The crystal structure of poly[μ2-aqua- aqua-(μ3-(E)-2-(4-((2-carbamothioylhydrazineylidene)methyl)phenoxy)acetato-κ3 O:S:S)sodium(I)], C10H14N3O5SNa
  36. The twinned crystal structure of [4,4′-bipyridine]-1,1′-diium hexachloridostannate(IV), C10H10N2SnCl6
  37. The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylate-k2 N,O)copper(II)], C34H24N4O4Cu
  38. Crystal structure of trans-1,2-bis(pyridinium-4-yl) ethylene bis(2-carboxy-4-bromobenzoate) – water (1/4), C14H14BrNO6
  39. 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
  40. Crystal structure of a second modification of Pachypodol, C18H16O7
  41. 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
  42. The crystal structure of catena-poly[(m2-4,4′-bipyridine-κ2 N:N)-bis(6-phenylpyridine-2-carboxylato-κ2 N,O) zinc(II)], C34H24N4O4Zn
  43. The crystal structure of hexaquamagnesium(II) (2,4-bis(nitroimino)-6-oxo-1,3,5-triazinane-1,3-diide), C3H15MgN7O12
  44. The crystal structure of 7-Bromo-2-(4-chloro-phenyl)-quinoxaline, C14H9BrClN2
  45. Crystal structure of methyl 4-{[4-(4-cyanobenzamido)phenyl]amino}benzofuro[2,3-d]pyrimidine-6-carboxylate, C26H17N5O4
  46. 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
  47. 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
https://doi.org/10.1515/ncrs-2021-0430
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. 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
  4. The crystal structure of 2-(2-methyl-6-phenyl-4H-pyran-4-ylidene)-1H-indene-1,3(2H)-dione, C21H14O3
  5. Crystal structure of bis((1-methylbenzimidazol-2-yl)methyl)amine, C18H19N5
  6. Crystal structure of (E)-N′-(1-(2-hydroxy-4-methoxyphenyl)ethylidene) isonicotinohydrazide, C15H15N3O3
  7. Crystal structure of 2-((4-phenyl-5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl)thio)acetonitrile, C15H11N5S
  8. The crystal structure of 2,2′-((1E,1′E)-hydrazine-1,2-diylidenebis(methaneylylidene))bis(4-chlorophenol), C14H10Cl2N2O2
  9. Dichlorido-{2,6-bis(4,5-dihydro-1H-pyrazol-3-yl)pyridine-κ3 N,N′,N″}zinc(II), C11H9C12N5Zn
  10. The crystal structure of dichlorido-(2-((4-phenyl-2H-1,2,3-triazol-2-yl)methyl)pyridine-κ2N,N′)palladium(II), C14H12Cl2N4Pd
  11. The crystal structure of 1-(N1-benzyl-2-methyl-4-nitro-imidazol-5-yl)-4-(prop-2-yn-1-yl) piperazine, C18H21N5O2
  12. Crystal structure of (μ4-(1,2,4,5-tetra(1,2,4-triazol-1-ylmethyl)-benzene-κ4N:N1:N2:N3)disilver(I) diperchlorate
  13. The crystal structure of 1-(2-bromoethane)-4-amine-3,5-dinitropyrazole, C5H6Br1N5O4
  14. Crystal structure of (E)-1-(4-benzyl-3,5-dioxomorpholin-2-ylidene)ethyl acetate, C15H15N1O5
  15. 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
  16. Crystal structure of (E)-N′-(1-(5-chloro-2-hydroxyphenyl) ethylidene)thiophene-2-carbohydrazide, C13H11ClN2O2S
  17. The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylato-k2 N,O)cobalt(II)]-monohydrate, C36H26N4O5Co
  18. Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-3-hydroxybenzo-hydrazide monohydrate, C14H13ClN2O4
  19. Crystal structure of 1,1′-(methylene)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2S:S)nickel(II), C42H30N14Ni2S8
  20. 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
  21. The crystal structure of 1-methyl-1H-pyrazol-2-ium nitrate, C4H7O3N3
  22. The crystal structure of 4,4′-diselanediylbis(8-(hexyloxy)-3,6-dimethyl-1-(piperidin-1-yl)isoquinoline-7-carbonitrile), C46H60N6O2Se2
  23. The crystal structure of tris(6-methylpyridin-2-yl)phosphine selenide, C18H18N3PSe
  24. The crystal structure of 1,2-bis(2,4-dinitro-1H-imidazol-1-yl)ethane ─ acetone (1/1), C11H12N8O9
  25. 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
  26. The crystal structure of tris(4-methyl-1H-pyrazol-1-yl)methane, C13H16N6
  27. The crystal structure of 5,6-dichloro-2-(quinolin-8-yl)isoindoline-1,3-dione, C17H8Cl2N2O2
  28. Crystal structure of (E)-(2-methoxy-benzylidene)-(4-[1,2,4]triazol-1-yl-phenyl)-amine, C16H14N4O
  29. 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
  30. Crystal structure of tetraaqua-tris(nitrato-κ2 O,O′) erbium(III) monohydrate, Er(NO3)3·5H2O, H10ErN3O14
  31. The crystal structure of 1-methyl-2-nitro-1H-imidazole 3-oxide, C4H5N3O3
  32. The crystal structure of 1-methyl-2-nitroimidazole, C4H5N3O2
  33. The crystal structure of 2-carboxyl-4-nitroimidazole monohydrate, C4H5N3O5
  34. Crystal structure of bis[hydrido-hexaphenylcarbodiphosphoran][tetra-trifluoromethyl-(μ-diiodo)-diplatinat]
  35. The crystal structure of poly[μ2-aqua- aqua-(μ3-(E)-2-(4-((2-carbamothioylhydrazineylidene)methyl)phenoxy)acetato-κ3 O:S:S)sodium(I)], C10H14N3O5SNa
  36. The twinned crystal structure of [4,4′-bipyridine]-1,1′-diium hexachloridostannate(IV), C10H10N2SnCl6
  37. The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylate-k2 N,O)copper(II)], C34H24N4O4Cu
  38. Crystal structure of trans-1,2-bis(pyridinium-4-yl) ethylene bis(2-carboxy-4-bromobenzoate) – water (1/4), C14H14BrNO6
  39. 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
  40. Crystal structure of a second modification of Pachypodol, C18H16O7
  41. 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
  42. The crystal structure of catena-poly[(m2-4,4′-bipyridine-κ2 N:N)-bis(6-phenylpyridine-2-carboxylato-κ2 N,O) zinc(II)], C34H24N4O4Zn
  43. The crystal structure of hexaquamagnesium(II) (2,4-bis(nitroimino)-6-oxo-1,3,5-triazinane-1,3-diide), C3H15MgN7O12
  44. The crystal structure of 7-Bromo-2-(4-chloro-phenyl)-quinoxaline, C14H9BrClN2
  45. Crystal structure of methyl 4-{[4-(4-cyanobenzamido)phenyl]amino}benzofuro[2,3-d]pyrimidine-6-carboxylate, C26H17N5O4
  46. 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
  47. 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
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