Abstract
C18H19N5, triclinic,
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.

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] |
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
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].
Funding source: Hubei Minzu University Null
Award Identifier / Grant number: PY21016
Award Identifier / Grant number: PY21016
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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: This work is supported by High Level Scientific Research Achievements In-school Cultivation Project of Hubei Minzu University (PY21016).
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Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
References
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© 2021 Meng Gaoxiang et al., 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