Startseite Naturwissenschaften The crystal structure of 2-(3,4–dichlorobenzyl)-1H-benzimidazole, C14H10Cl2N2
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The crystal structure of 2-(3,4–dichlorobenzyl)-1H-benzimidazole, C14H10Cl2N2

  • Shu-Fen Hou ORCID logo EMAIL logo , Ailing Zhang , Chunling Xin und Mengran Fan
Veröffentlicht/Copyright: 15. Januar 2024

Abstract

C14H10Cl2N2, monoclinic, P21/n (no. 14), a = 9.4145(9) Å, b = 14.8530(15) Å, c = 10.0405(11) Å, β = 116.714(5)°, V = 1254.1(2) Å3, Z = 4, Rgt(F) = 0.0653, wRref(F2) = 0.1901, T = 293 K.

CCDC no.: 2307842

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: 0.32 × 0.14 × 0.06 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.50 mm−1
Diffractometer, scan mode: φ and ω
θmax, completeness: 25.0°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 5922, 2198, 0.081
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 1284
N(param)refined: 163
Programs: Bruker [1], Olex2 [2], SHELX [3]
Table 2:

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

Atom x y z Uiso*/Ueq
Cl1 1.60722 (14) 0.07615 (10) 0.70612 (16) 0.0807 (5)
Cl2 1.30413 (16) −0.03238 (10) 0.67010 (15) 0.0782 (5)
N1 0.9358 (4) 0.2666 (2) 0.3802 (4) 0.0431 (9)
H1 1.033704 0.264851 0.446187 0.052*
N2 0.7183 (4) 0.2377 (2) 0.1699 (4) 0.0416 (9)
C1 0.8715 (5) 0.2208 (3) 0.2487 (4) 0.0385 (10)
C2 0.6823 (4) 0.2977 (3) 0.2569 (4) 0.0403 (10)
C3 0.8176 (4) 0.3160 (3) 0.3893 (4) 0.0384 (9)
C4 0.8163 (5) 0.3729 (3) 0.4974 (5) 0.0529 (12)
H4 0.908079 0.384136 0.584985 0.063*
C5 0.6731 (6) 0.4123 (3) 0.4701 (5) 0.0580 (13)
H5 0.667753 0.450952 0.540517 0.070*
C6 0.5362 (5) 0.3950 (3) 0.3381 (5) 0.0568 (12)
H6 0.441316 0.422585 0.322560 0.068*
C7 0.5375 (5) 0.3381 (3) 0.2302 (5) 0.0510 (12)
H7 0.445531 0.326935 0.142780 0.061*
C8 0.9642 (5) 0.1583 (3) 0.2010 (5) 0.0469 (11)
H8A 0.975925 0.185512 0.118618 0.056*
H8B 0.904384 0.102982 0.164837 0.056*
C9 1.1279 (5) 0.1355 (3) 0.3236 (5) 0.0430 (10)
C10 1.1430 (5) 0.0706 (3) 0.4288 (5) 0.0458 (11)
H10 1.053365 0.040091 0.420999 0.055*
C11 1.2898 (5) 0.0511 (3) 0.5446 (5) 0.0485 (11)
C12 1.4234 (5) 0.0967 (3) 0.5565 (5) 0.0517 (11)
C13 1.4102 (5) 0.1588 (3) 0.4512 (6) 0.0562 (12)
H13 1.500251 0.188258 0.457714 0.067*
C14 1.2634 (5) 0.1778 (3) 0.3355 (5) 0.0502 (11)
H14 1.255515 0.220020 0.264104 0.060*

1 Source of material

All chemicals were purchased from commercial sources and used as received. The 2-(3,4–dichlorobenzyl)-1H-benzimidazole was synthesized according to reported method by direct condensation of carboxylic acids with benzene-1,2-diamine catalyst by boron acid [4, 5]. To a stirred solution of benzene-1,2-diamine (216 mg, 2.0 mmol) in 10 mL xylenes was added 2-(3,4-dichlorophenyl) acetic acid (612 mg, 3 mmol) and boric acid B(OH)3 (12 mg, 0.2 mmol). After refluxing for 16 h, the volatile in the solution was removed under vacuum, and the residue was extracted with EtOAc (50 mL). The resulting solution was washed with saturated NaHCO3 solution twice, dried over anhydrous Na2SO4 and then concentrated under reduced pressure. The residue was purified by silica gel flash column chromatography (ethyl acetate:hexane = 1:10) to afford the title compound 365 mg (yield 65 %). Crystals were obtained by recrystallization the product from methanol.

2 Experimental details

Coordinates of hydrogen atoms were included using constraints or restraints. Their Uiso values were set to 1.2Ueq of the parent atoms.

3 Comment

Nitrogen-containing heterocyclic compounds are very common organic compounds widely used in pesticides and medicine [6, 7]. N–Arylated imidazoles are compounds of particular significance owing to their excellent applications in plant growth regulator, therapeutic agent, herbicide, etc. [8], [9], [10]. Due to its potential applications in pharmaceutical activities, the synthesis of imidazoles has attracted wide interests among scientists [11], [12], [13]. As displayed in the Figure, there is one molecule in the asymmetric unit of the title compound. The C1–N2 bond length of 1.320(5) Å is shorter than the C1–N1, with 1.362(5) Å, which suggests that the C1–N2 bond is the double bond. In the crystal, the benzoimidazole parts exhibit a planar structure. The average length of the C–Cl bond is 1.732 Å. Bond lengths and angles are as expected [14, 15].


Corresponding author: Shu-Fen Hou, College of Chemical Engineering and Environmental Chemistry, Weifang University, Weifang 261061, China, E-mail:

Award Identifier / Grant number: ZR2022QB107

Funding source: Doctoral Research Foundation of Weifang University University–Industry

Award Identifier / Grant number: 2022BS08

Funding source: University–Industry Collaborative Education Program

Award Identifier / Grant number: 220605042195002 and 220605042234119

Funding source: Weifang Science and Technology Development Plan

Award Identifier / Grant number: 2021GX004

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

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

  3. Research funding: This work was supported by Natural Science Foundation of Shandong Province (No. ZR2022QB107); Doctoral Research Foundation of Weifang University University–Industry (2022BS08); University–Industry Collaborative Education Program (No. 220605042195002 and No. 220605042234119); Weifang Science and Technology Development Plan (Grant No. 2021GX004).

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Received: 2023-11-21
Accepted: 2023-12-28
Published Online: 2024-01-15
Published in Print: 2024-04-25

© 2023 the author(s), published by De Gruyter, Berlin/Boston

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

Artikel in diesem Heft

  1. Frontmatter
  2. New Crystal Structures
  3. Solvothermal synthesis and crystal structure of aqua-tris(p-acetamidobenzoate-κ2O,O′)-(2,2′-bipyridine-κ2N,N′)terbium(III) - water - methanol (1/1/1)
  4. Crystal structure of hexaaquazinc(II) catena-poly[bis(1-(3-carboxyphenyl)-5-methyl-4-oxo-1,4-dihydropyridazine-3-carboxylato-κ2O,O′)-bis(μ2-1-(3-carboxyphenyl)-5-methyl-4-oxo-1,4-dihydropyridazine-3-carboxylato-κ2O:O′)trizinc(II)] hexahydrate C26H36N4O20Zn2
  5. The crystal structure of valinyl-N-ium-4-(5-(thiophen-2-yl)isoxazol-3-yl)phenyl trifluoroacetate
  6. Crystal structure of bis(3,5-diisopropyl-1H-pyrazol-4-ammonium) tetrafluoroterephthalate, 2[C9H18N3][C8F4O4]
  7. Crystal structure of aqua-octakis(μ3-salicylato)-(1,10-phenanthroline)-(acetonitrile)-dicobalt(II)-trititanium(IV), C70H45N3O25Co2Ti3
  8. Crystal structure of catena-poly[aqua-(μ2-4,4′-diimidazole diphenyl ether-κ2N:N′)-(sulfato-κ1O)-cobalt(II)] – dimethylformamide (2/1), C39H37CoN9O8S
  9. Crystal structure of (5R,8R,9R,10R,12R, 13R,14R,17S)-2-(E-3-fluorobenzylidene)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl) hexadecahydro-3H-cyclopenta[a]phenanthren-3-one, C37H53FO3
  10. Crystal structure of (Z)-4-((4,5,6-trimethoxy-3-oxobenzofuran-2(3H)-ylidene)methyl)phenyl diphenylphosphinate, C30H25O7P
  11. Crystal structure of 3-((5-methylpyridin-2-yl)amino)-1-phenylpropan-1-one, C15H16N2O
  12. The crystal structure of (R)-9-(5-methoxy-2-methyl-2,3-dihydro-1H-cyclopenta[a]naphthalen-1-ylidene)-9H-thioxanthene, C28H22OS
  13. Crystal structure of diaqua-bis[1-(1-(hydroxymethyl)-1H-pyrazol-3-yl)-5-methyl-1H-1,2,3-triazole-4-carboxylato-κ2N,O)] manganese(II), C16H20MnN10O8
  14. The crystal structure of t-butyl 7-[4-(4-fluorophenyl)-2-[(methanesulfonyl)(methyl)amino]-6-(propan-2-yl)pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoate, C26H36FN3O6S
  15. The crystal structure of samarium sulfate pentahydrate, Sm2(SO4)3(H2O)5
  16. The crystal structure of [triaqua-(8-carboxymethoxy-quinoline-2-carboxylate-κ 4 N,O,O,O)-zinc(II)] monohydrate, C12H15NO9Zn
  17. The crystal structure of 2,3-difluoro-11H-benzo-[4,5]imidazo[2,1-a]isoindol-11-one, C14H6F2N2O
  18. The crystal structure of 2,3-di(9H-carbazol-9-yl)-9H-fluoren-9-one, C37H22N2O
  19. The crystal structure of 5-(2-chloro-3-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)-10,11-dihydro-5H-dibenzo[b,f]azepine, C40H39ClN2
  20. Crystal structure of 2-bromo-1-hydroxy-3-(3-methylbut-2-enyloxy)-9H-xanthen-9-one, C18H15BrO4
  21. Crystal structure of bis(μ2-benzenesulfonato-κ2O:O′)-bis(μ2-6,6′-((ethane-1,2-diylbis(azaneylylidene))bis(methaneylylidene))-bis(2-methoxyphenolato-κ6O,O′:O′,N,N′,O′′:O′′,O′′′))disodium(I)dicopper(II)
  22. The crystal structure of (E)-1,2-bis(benzo[e][1,2]azaborinin-2(1H)-yl)ethene, C18H16B2N2
  23. Crystal structure of 3-oxo-urs-12-en-28-benzyl ester, C37H52O3
  24. The crystal structure of ethyl (E)-1-chloro-3-(4-chloro-1-methyl-1H-indole-2-carbonyl)-4-oxo-2-phenylcyclooct-2-ene-1-carboxylate, C27H25Cl2NO4
  25. The crystal structure of 4,4′-((5-bromo-2-iodo-1,3-phenylene)bis(oxy))bis(tert-butylbenzene) ─ ethanol (2/1), C26H28BrIO2
  26. Crystal structure of (E)-1-(4-(benzyloxy)-2-hydroxyphenyl)-3-(dimethylamino)prop-2-en-1-one, C18H19NO3
  27. The crystal structure of N1,N3-bis(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)\ propanediamide hydrate, C25H26N6O4, 2(H2O)
  28. The crystal structure of 2,5-bis[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)amino]cyclohexa-2,5-diene-1,4-dione, C28H26N6O4
  29. Crystal structure of 3,4-bis[2-(hydroxymethyl)-pyrrolidin-1-yl] cyclobut-3-ene-1,2-dione hydrate, C14H22N2O5
  30. The crystal structure of 2-(3,4–dichlorobenzyl)-1H-benzimidazole, C14H10Cl2N2
  31. The crystal structure of 2-(2-((4,6-dimethoxypyrimidin-2-yl)oxy)phenyl)-4-(piperidin-1-yl)-5H-chromeno[2,3-d]pyrimidine, C28H27N5O4
  32. The crystal structure of 6-(benzofuran-2-yl)-2-oxo-4,5-diphenyl-3,4-dihydro-2H-pyran-3-carbonitrile, C26H17NO3
  33. Crystal structure of N-(4-bromobenzyl)-3-(difluoromethyl)-1-methyl-N-(pyridin-2-yl)-1H-pyrazole-4-carboxamide, C18H15BrF2N4O
  34. The crystal structure of the host-guest complex: N-{5-[2-(2,6-dimethylphenoxy)acetamido]-4-hydroxy-1,6-diphenylhexan-2-yl}-3-methyl-2-(2-oxo-1,3-diazinan-1-yl)butanamide-diethyl ether (2/1)
  35. The crystal structure of (Z)-4-amino-N-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H17N3O2
  36. The crystal structure of diethyl 1,4-dihydro-2,6-dimethyl-4-(3-cyanophenyl)-3,5-pyridinedicarboxylate, C20H22N2O4
  37. Crystal structure of 3-(5-((4-(difluoromethoxy)phenyl) sulfonyl)-3,4,5,6-tetrahydropyrrolo[3,4-c]pyrrol-2(1H)-yl) oxetane-3-carboxamide, C17H19F2N3O5S
  38. Crystal structure of 2-((2,6-dichloro-4-(3,5-dimethylisoxazol-4-yl)phenyl)amino)-N-(2-(4-methylpiperazin-1-yl)ethyl)benzamide hydrate, C25H37Cl2N5O6
  39. Crystal structure of 3-(benzo[d]thiazol-2-yl)-5-bromo-2-hydroxybenzaldehyde, C14H8BrNO2S
  40. Crystal structure of 3-(difluoromethyl)-1-methyl-N-(pyridin-2-yl)-1H-pyrazole-4-carboxamide, C11H10F2N4O
  41. Crystal structure of 3-(2-ethoxy-2-oxoethyl)-1-isopropyl-1H-imidazol-3-ium hexafluoridophosphate(V), C20H34F12N4P2
  42. Crystal structure of ethyl 5,6-dichloro-2-methyl-2,3-dihydro-1 H-benzo[d]imidazole-2-carboxylate, C11H12Cl2N2O2
  43. The crystal of structure of (OC-6-22)-pentakis(acetonitrile)bromidoruthenium(II)bromide monohydrate, C10H15Br2N5Ru
  44. Crystal structure of (2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(((4aS,5R,6S)-1-oxo-5-vinyl-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-6-yl)oxy)tetrahydro-2H-pyran-3-yl 2,3-dihydroxybenzoate hydrate, C23H26O12·H2O
  45. The crystal structure of (E)-4-amino-N′-(1-(4-fluorophenyl)propylidene)benzohydrazide, C16H16FN3O
  46. The crystal structure of 2′-(9H-carbazol-9-yl)-[1,1′-binaphthalen]-2-amine, C32H22N2
  47. Crystal structure of poly[μ3-diiodido-[μ2-di(1H-pyrazol-1-yl)methane-κ2N,N′)]dicopper(I)], C7H8Cu2I2N4
  48. Crystal structure of 3-amino-N′-hydroxy-1H-pyrazole-4-carboximidamide, C4H7N5O
  49. The crystal structure of 1,3-diacetyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, C8H10O4N4
  50. Crystal structure of catena-poly[aqua-(μ2-1,4-diazabicyclo[2.2.2]octane-k2N: N′)-bis(sorbato-κ1O)-copper(II), C18H28CuN2O5
  51. Crystal structure of catena-poly[triaqua-(μ2 -1-(4-carboxylatophenyl)-4-oxo-1,4-dihydropyridazine-3-carboxylato-κ3O,O′:O′′)manganese(II)], C12H12N2O8Mn
  52. The crystal structure of [hexaaquamagnesium(II)] 4-[(pyridine-4-carbonyl)-amino]-phthalate trihydrate, C14H26N2O14Mg
  53. Crystal structure of 1-(p-tolylphenyl)-4-(2-furoyl)-3-methyl-1H-pyrazol-5-ol, C16H14N2O3
  54. The crystal structure of bis(1,4,7,10,13-pentaoxacyclopentadecane)-potassium(I) dichloridocopper(I), C20H40Cl2CuKO10
  55. The crystal structure of tris(tetra-n-butylammonium) hexanitrato-κ2O,O′-lanthanium(III) C48H108N9O18La
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