Startseite The crystal structure of 1-(2-chlorophenyl)-3-(p-tolyl)urea, C14H13ClN2O
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The crystal structure of 1-(2-chlorophenyl)-3-(p-tolyl)urea, C14H13ClN2O

  • Lei Han , Mo Du , Xiaohua Li und Wenqiang Tang ORCID logo EMAIL logo
Veröffentlicht/Copyright: 5. Juni 2024

Abstract

C14H13ClN2O, monoclinic, P21/c (no. 14), a = 23.904(2) Å, b = 4.6173(3) Å, c = 11.6906(13) Å, β = 96.895(9)°, V = 1281.0(2) Å3, Z = 4, R gt(F) = 0.0646, wR ref(F 2) = 0.1314, T = 293 K.

CCDC no.: 2357517

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: Colourless block
Size: 0.66 × 0.57 × 0.49 mm
Wavelength: MoKα radiation (0.71073 Å)
μ: 0.29 mm−1
Diffractometer, scan mode: SuperNova, ω
θ max, completeness: 29.1°, >99 %
N(hkl)measured, N(hkl)unique, R int: 5,335, 2,883, 0.028
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 1970
N(param)refined: 164
Programs: Bruker, 1 Shelx, 2 , 3 Olex2 4
Table 2:

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

Atom x y z U iso*/U eq
C1 0.89499 (11) 0.4159 (5) 0.2587 (2) 0.0313 (6)
C2 0.93491 (12) 0.5340 (6) 0.1967 (3) 0.0388 (7)
H2 0.972432 0.478538 0.212578 0.047*
C3 0.91948 (13) 0.7333 (7) 0.1116 (3) 0.0435 (8)
H3 0.946532 0.815051 0.070533 0.052*
C4 0.86368 (13) 0.8116 (7) 0.0873 (3) 0.0449 (8)
H4 0.853135 0.947584 0.030054 0.054*
C5 0.82330 (12) 0.6890 (6) 0.1475 (3) 0.0392 (7)
H5 0.785661 0.740515 0.129457 0.047*
C6 0.83843 (11) 0.4897 (5) 0.2345 (2) 0.0302 (6)
C7 0.75951 (10) 0.5081 (6) 0.3497 (2) 0.0307 (6)
C8 0.68148 (11) 0.4433 (6) 0.4664 (2) 0.0326 (6)
C9 0.64316 (12) 0.6440 (6) 0.4173 (3) 0.0430 (7)
H9 0.647205 0.722767 0.345567 0.052*
C10 0.59882 (12) 0.7276 (7) 0.4751 (3) 0.0507 (9)
H10 0.573630 0.865490 0.441582 0.061*
C11 0.59051 (12) 0.6147 (7) 0.5802 (3) 0.0442 (8)
C12 0.62907 (13) 0.4162 (7) 0.6289 (3) 0.0507 (8)
H12 0.624715 0.337719 0.700507 0.061*
C13 0.67464 (12) 0.3301 (7) 0.5728 (3) 0.0454 (8)
H13 0.700410 0.196201 0.607287 0.055*
C14 0.54082 (14) 0.7063 (9) 0.6415 (3) 0.0708 (11)
H14A 0.539562 0.588884 0.708917 0.106*
H14B 0.506522 0.681794 0.590640 0.106*
H14C 0.544976 0.906049 0.663669 0.106*
Cl1 0.91539 (3) 0.17505 (16) 0.37003 (7) 0.0466 (2)
N1 0.79765 (9) 0.3569 (4) 0.2957 (2) 0.0349 (6)
H1 0.796934 0.170850 0.298935 0.042*
N2 0.72612 (9) 0.3399 (5) 0.4078 (2) 0.0381 (6)
H2A 0.732444 0.156459 0.409335 0.046*
O1 0.75674 (8) 0.7736 (4) 0.34665 (19) 0.0440 (5)

1 Source of materials

Weigh 0.107 g of p-toluidine (1 mmol) and 0.153 g of 1-chloro-2-isocyanatobenzene (1 mmol), and transfer them into a 50 mL flask. Add 15 mL of dichloromethane, stirring until complete dissolution. Heat the mixture to 50 °C and maintain stirring for 2 h until the reaction completes, resulting in the formation of a white precipitate. Cool the mixture to room temperature, then remove the dichloromethane solvent via vacuum drying to obtain the crude product of the target compound. Dissolve 0.05 g of this crude product in 15 mL of ethanol, employing ultrasonication and heating to ensure complete dissolution of the solid. Subsequently, allow the ethanol to evaporate slowly at room temperature, and collect the crystals of the target compound after 1 week.

2 Experimental details

The structure was solved by Direct Methods and further refined using the Shelxl 2 and Shelxt 3 software. The crystallographic analysis, refinement of the structure, and its graphical representation were carried out using the Olex2 4 software.

3 Comment

Urea-based organic compounds are pivotal in the realm of drug discovery and development, owing to their distinctive chemical structures and extensive biological activities. 5 A variety of urea derivatives have been characterized in their crystalline forms, where intermolecular hydrogen bonding predominantly dictates the molecular assembly into crystalline lattices. 6 14 This paper introduces a crystal structure of a urea derivative and delves into the role of intermolecular hydrogen bonds in shaping this structure.

As shown in the figure, the atoms in the title compound form three planes. The dihedral angle between the plane of the tolyl group and the urea group is 46.0°, the dihedral angle between the chlorophenyl group and the urea group is 51.1°, and the dihedral angle between the tolyl group and the chlorophenyl group is 28.6°. All bond lengths and angles are within normal ranges and are consistent with structures similar to this one. 8 16

Intermolecular interactions occur between the molecules through hydrogen bonds in the urea groups. The bond angle of N2–H2A–O1 is 155.40(18)°, and the bond length of H2A–O1 is 2.025(2) Å. The bond angle of N1–H1–O1 is 149.95(17)°, and the bond length of H1–O1 is 2.174(2) Å.


Corresponding author: Wenqiang Tang, Xianyang Key Laboratory of Molecular Imaging and Drug Synthesis, School of Pharmacy, Shaanxi Institute of International Trade & Commerce, Xianyang, Shaanxi, China, E-mail:

  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 was financially supported by the projects of key research and development project of Shaanxi Provincial Science and Technology Department (2022SF-448), Scientific research plan project of Shaanxi Provincial Department of Education (22JK0276), the Xianyang key laboratory of molecular imaging and drug synthesis (2021QXNL-PT-0008), the 2023 key research and development project of the Xianyang Science and Technology Bureau (L2023-ZDYF-SF-030), the key research and development project of Shaanxi Provincial Science and Technology Department (2023-YBSF-036).

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

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Received: 2024-04-28
Accepted: 2024-05-23
Published Online: 2024-06-05
Published in Print: 2024-08-27

© 2024 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. The crystal structure of hexaquazinc(II) poly[hexakis(μ2-4-methylbenzenesulfinato-κ2O:O′) dizinc(II)]
  4. The crystal structure of poly[((2-(4,5-dihydro-1H-pyrazol-4-yl)-1,3-dioxoisoindoline-5-carbonyl)oxy)(1-(dimethylamino)ethoxy)zinc[II]], C16H14ZnN4O5
  5. Crystal structure of bis[(triaqua-4-iodopyridine-2,6-dicarboxylato-κ 3 N,O,O )cobalt(II)] trihydrate, C14H22N2O17I2Co2
  6. Crystal structure of bis(methanol-κO)-bis(nitrato-kO)-bis(1-((2-(2-chloro-4-(4-chlorophenoxy)phenyl)-4-methyl-1,3-dioxolan-2-yl)methyl)-1H-1,2,4-triazole-κN)cadmium(II), C40H42O14N8Cl4Cd
  7. Crystal structure of poly[μ2-dichlorido-(μ2-1-[(2,4-dimethyl-1H-triazole-1-yl)methyl]-1H-benzotriazole-κ2N:N′)cadmium(II)], C11H12CdN6Cl2
  8. The crystal structure of (3aS, 4R, 7S, 7aR)-hexahydro-4, 7-methano-1H-isoindole-1, 3-(2H)-dione, C9H11NO2
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  10. Crystal structure of 3,3′-dimethoxy-4,4′-oxy-di-benzaldehyde, C16H14O5
  11. The crystal structure of tetrakis(μ 2-2-amino-3,5-dibromobenzoate-κ 2 O:O′)-octakis(n-butyl-κ 1 C)-bis(μ 3-oxo)tetratin(II), C60H92Br8N4O10Sn4
  12. Crystal structure of methyl-1-(naphthalen-1-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b] indole-3-carboxylate, C23H20N2O2
  13. Crystal structure of tetrapropylammonium bicarbonate–1-(diaminomethylene)thiourea(1/1)
  14. Crystal structure of 6,6′-((1E,1′E)-((2-phenylpyrimidine-4,6-diyl)bis(hydrazin-2-yl-1-ylidene))bis(methaneylylidene))bis(2-methoxyphenol)monohydrate, C26H26N6O5
  15. Crystal structure of bis(N,N,N-trimethylbutanaminium) tetrathiotungstate(VI), (BuMe3N)2[WS4]
  16. The crystal structure of 2,3,9-triphenyl-9-(2-phenylbenzofuran-3-yl)-9H-9λ 5-benzo[4,5][1,2]oxaphospholo[2,3-b][1,2,5]oxadiphosphole 2-oxide, C40H28O4P2
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  18. Crystal structure of N-(benzo[d]thiazol-2-yl)-2-chloroacetamide, C9H7ClN2OS
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  20. Crystal structure of 3,4-dimethoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C23H24O5
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  24. Crystal structure of diaqua-bis(1-(3-carboxyphenyl)-5-methyl-4-oxo-1,4-dihydropyridazine3-carboxylato-O,O′)-cobalt(ii)dihydrate, C26H36N4O14Co
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  27. Crystal structure of (3R)-1-(3,5-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate chloride, C21H23ClN2O4
  28. Synthesis and crystal structure of 3-(4,5-dihydroisoxazol-3-yl)-2-methyl-4-(methylsulfonyl)benzoic acid, C12H13NO5S
  29. The crystal structure of hexaaquamagnesium(II) bis-3-(1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-α]pyridin-1-yl)benzoate, C36H42N4O10Mg
  30. Crystal structure of 4-formyl-2-methoxyphenyl 2-acetoxybenzoate, C17H14O6
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  32. Crystal structure of 4,8a-bis(4-chlorophenyl)-1,5,6-tris(4-fluorobenzyl)-1,4,4a,4b,5,6,8a,8b-octahydrocyclobuta[1,2-b:3,4-c′]dipyridine-3,8-dicarbonitrile, C45H33Cl2F3N4
  33. Crystal structure of benzo[d][1,3]dioxol-5-ylmethyl 2-(6-methoxynaphthalen-2-yl)propanoate, C22H20O5
  34. Crystal structure of N-benzoyl-N-phenylhydroxylaminato-dicarbonylrhodium(I), [Rh(BNA)CO2]
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  36. The crystal structure of methyl ((4-aminobenzyl)sulfonyl)-d-prolinate, C13H18N2O4S
  37. The crystal structure of dichlorido-(N-isopropyl-N-(pyridin-2-ylmethyl)propan-2-amine-κ 2 N, N′)palladium(II), C12H20N2PdCl2
  38. Crystal structure of poly[(μ 2-5-hydroxyisophthalato-κ4 O,O′:O″,O‴)-(μ 2-1,4-bis(2-methylimidazolyl)-1-butene-N:N′)nickel(II)], C20H20NiN4O5
  39. The crystal structure of {hexakis(1-methyl-1H-imidazole-κ 1 N)cobalt(II)}(μ 2-oxido)-hexaoxido-dimolybdenum(VI)— 1-methyl-1H-imidazole (1/2), C32H48CoMo2N16O7
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  42. Crystal structure of 1-(4-bromophenyl)-3-(diphenylphosphoryl)-3-hydroxypropan-1-one, C21H18BrO3P
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  52. The crystal structure of 1-(2-chlorophenyl)-3-(p-tolyl)urea, C14H13ClN2O
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  56. The crystal structure of 1,4-bis(1H-imidazol-3-ium-1-yl)benzene dinitrate, C12H12N4 2+·2(NO3 )
  57. Crystal structure of tris(hexafluoroacetylacetonato-κ2O,O′) bis(triphenylphosphine oxide-κ1O)samarium(III), C51H33F18O8P2Sm
  58. Crystal structure of 1-(4-(dimethylamino)phenyl)-2,3-bis(diphenylphosphoryl)propan-1-one, C35H33NO3P2
  59. Crystal structure of diaqua[bis(μ 2-pyridine 2,6-dicarboxylato) bismuth(III) potassium(I)], C14H10BiKN2O10
  60. Crystal structure of (R)-N, N -dimethyl-[1, 1′-binaphthalene]-2, 2′-diamine, C22H20N2
  61. Crystal structure of 1-phenyl-4-(2-furoyl)-3-furyl-1H-pyrazol-5-ol, C18H12N2O4
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