Startseite The crystal structure of 1-(4-bromophenyl)-3-(2-chlorobenzyl)urea, C14H12BrClN2O
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The crystal structure of 1-(4-bromophenyl)-3-(2-chlorobenzyl)urea, C14H12BrClN2O

  • Zhihong Zhu ORCID logo EMAIL logo und Lilei Zhang ORCID logo
Veröffentlicht/Copyright: 4. November 2022
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Zeitschrift für Kristallographie - New Crystal Structures
Aus der Zeitschrift Zeitschrift für Kristallographie - New Crystal Structures Band 238 Heft 1

Abstract

C14H12BrClN2O, monoclinic, P21/c (no. 14), a = 13.4072(6) Å, b = 8.6103(5) Å, c = 12.3824(6) Å, β = 100.475(4), V = 1405.60(12) Å3, Z = 4, Rgt (F) = 0.0499, wRref (F 2) = 0.1215, T = 173 K.

CCDC no.: 2212900

The crystal 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 0.27 × 0.25 × 0.22 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 3.11 mm−1
Diffractometer, scan mode: Multiwire proportional, φ and ω-scans
θ max, completeness: 29.3°, >99%
N(hkl)measured, N(hkl)unique, R int: 6337, 3236, 0.026
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 1727
N(param)refined: 173
Programs: CrysAlisPRO [1], OLEX2 [2], SHELX [3, 4]
Table 2:

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

x y z U iso*/U eq
Br1 0.09861(4) 0.47977(6) 0.33688(4) 0.0922(3)
N1 0.5800(2) 0.1958(3) 0.8092(2) 0.0509(8)
H1 0.553621 0.115781 0.838190 0.061*
N2 0.4292(2) 0.2172(3) 0.6905(2) 0.0469(7)
H2A 0.416253 0.125020 0.715289 0.056*
O1 0.54552(17) 0.4131(2) 0.7065(2) 0.0484(6)
C1 0.8128(3) 0.3575(4) 0.9918(3) 0.0606(11)
C2 0.8405(4) 0.4436(5) 1.0867(4) 0.0849(16)
H2 0.910143 0.459597 1.116717 0.102*
C3 0.7666(6) 0.5061(5) 1.1373(4) 0.0912(19)
H3 0.784681 0.568010 1.201334 0.109*
C4 0.6672(5) 0.4782(5) 1.0946(4) 0.0774(14)
H4 0.616078 0.520044 1.130091 0.093*
C5 0.6394(3) 0.3903(4) 1.0005(3) 0.0566(10)
H5 0.569633 0.372965 0.971983 0.068*
C6 0.7124(3) 0.3273(4) 0.9477(3) 0.0453(9)
C7 0.6863(2) 0.2304(4) 0.8440(3) 0.0476(9)
H7A 0.710528 0.286021 0.783700 0.057*
H7B 0.724049 0.131220 0.855849 0.057*
C8 0.5202(3) 0.2830(4) 0.7336(3) 0.0415(8)
C9 0.3539(3) 0.2847(3) 0.6093(3) 0.0402(8)
C10 0.2532(3) 0.2578(4) 0.6135(3) 0.0488(9)
H10 0.236455 0.198390 0.672342 0.059*
C11 0.1765(3) 0.3148(4) 0.5344(3) 0.0583(10)
H11 0.107539 0.294104 0.538007 0.070*
C12 0.2009(3) 0.4016(4) 0.4506(3) 0.0535(10)
C13 0.3001(3) 0.4315(4) 0.4429(3) 0.0558(10)
H13 0.316002 0.492304 0.384316 0.067*
C14 0.3771(3) 0.3706(4) 0.5231(3) 0.0479(9)
H14 0.446081 0.388513 0.518132 0.058*
Cl1 0.90662(8) 0.28220(16) 0.92618(10) 0.0922(4)

Source of materials

The chemical reagents 1-bromo-4-isocyanatobenzene, dichloromethane, and 2-chlorobenzylamine were purchased from Aladdin Biochemical Technology Co., Ltd with no further purification. The 1-bromo-4-isocyanatobenzene (198 mg, 1 mmol), dichloromethane (10 mL), and 2-chlorobenzylamine (142 mg, 1 mmol) were mixed and stirred for 24 h under normal temperature and pressure. Then, the organic solvent was removed by vacuum distillation. The crude product (80 mg) was dissolved in 10 mL ethanol with ultrasonic dispersion. The single crystal product of the title compound was obtained after two days by slow volatilization of the organic solvent.

Experimental details

The structure of the title compound was solved with the ShelXT [4] package and refined with the ShelXL [3] program. All hydrogen atoms were placed in idealized positions and refined as riding atoms. The U iso values were constrained to be 1.2 U eq of the parent atoms.

Comment

The urea group is an important structural fragment of many bioactive compounds, including many drug molecules such as Sorafenib, Donafenib, and Regorafenib [5, 6], which plays a significant role in target interaction drugs and the regulation of drug formation of compounds. Many references showed crystal structures of the derivatives with the urea group [7], [8], [9], [10], [11], [12], [13], [14], [15]. In this work, we report the single crystal structure of 1-(4-bromophenyl)-3-(2-chlorobenzyl)-urea, which provides an essential basis for studying urea derivatives.

As shown in the figure, the title compound adopts trans conformations with respect to the position of the 3-chloropropanoyl and 4-bromophenyl groups, respectively, against the C=O bond across their C–N bonds. The Br and Cl atoms replace H atoms in the two phenyl, and the lengths of C–Br and C–Cl bonds are 1.901(4) Å and 1.742(5) Å, respectively. The two halogenophenyl rings make a dihedral angle of 10.2(4)°. In the crystal, molecules are linked by N–H⃛O hydrogen bonds. The angle of hydrogen bonds N2–H2A⃛O1 is 154.70(18)°, and the length is 2.0856(19) Å. The angle of hydrogen bonds N1–H1⃛O1 is 141.87(17)°, and the length is 2.2025(19) Å. It indicates that the hydrogen bond plays an important role in maintaining the crystal structure. All bond lengths and angles are within a reasonable range [7, 11, 14].

Corresponding author: Zhihong Zhu, School of food and drug, Luoyang Polytechnic, Luoyang 471000, 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: None declared.

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

References

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Received: 2022-09-14
Accepted: 2022-10-14
Published Online: 2022-11-04
Published in Print: 2023-01-27

© 2022 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. Crystal structure of undecacalcium decaarsenide, Ca11As10
  4. Crystal structure of catena-poly[diiodido-(μ2-1,5-dimethyl-2-phenyl-4-((pyridin-4- ylmethylene)amino)-1,2-dihydro-3H -pyrazol-3-one-κ2 N: O)zinc(II)], C17H16I2N4OZn
  5. The crystal structure of 5,10,15,20-tetrakis(4-(tert-butyl)phenyl)porphyrin-21,23-diido-κ4 N 4-naphthalocyanido-κ4 N 4-neodymium(IV) - chloroform (1/6) C114H90N12Cl18Nd
  6. The crystal structure of 1-(4-bromophenyl)-3-(2-chlorobenzyl)urea, C14H12BrClN2O
  7. Crystal structure of bis[benzyl(methyl)carbamodithioato-κ 2 S,S′]-di-n-butyltin(IV), C26H38N2S4Sn
  8. Crystal structure of (E)-3-(2-(4-(diethylamino)-2-hydroxystyryl)-3,3-dimethyl-3H-indol-1-ium-1-yl)propane-1-sulfonate – methanol (1/2), C25H32N2O4S⋅2CH3OH
  9. Synthesis and crystal structure of {(N′,N″-(((ethane-1,2-diylbis(oxy))bis(2,1-phenylene))-bis(methaneylylidene))bis(2-hydroxybenzohydrazonato)-κ6 N 2 O 4}copper(II), C30H24CuN4O6
  10. The crystal structure of ((E)-2,4-dibromo-6-(((5-(nitro)-2-oxidophenyl)imino)methyl)phenolato-κ 3 N,O,O′)tris(pyridine-κN)manganese(II), C28H21Br2MnN5O4
  11. Synthesis and crystal structure of 1-((3R,10S,13R,17S)-10,13-dimethyl-3-(p-tolylamino)hexadecahydro-1H-cyclopenta-[a]phenanthren-17-yl)ethan-1-one, C28H41NO
  12. The crystal structure of 3-nitrobenzene-1,2-dicarboxylic acid—pyrazine-2-carboxamide(1/1), C13H10N4O7
  13. Crystal structure of poly[tetrakis(μ3-2-aminonicotinato-κ3N,O,O′)-(μ2-oxalato-κ4 O,O′:O″,O′″)-(μ4-oxalato-κ6 N:N′:O,O′:O″,O′″)dicopper(I)-disamarium(III)], [SmCu(C6N2H5O2)2(C2O4)] n
  14. The crystal structure of 2,3,4-trihydroxybenzoic- acid—pyrazine-2-carboxamide—water (1/1/1), C12H13N3O7
  15. Crystal structure of N-ethyl-4-[3-(trifluoromethyl)-phenyl]piperazine-1-carbothioamide, C14H18F3N3S
  16. The crystal structure of 3-anilino-1,4-diphenyl-4H-1,2,4-triazol-1-ium iodide, C20H17N4I
  17. The crystal structure of (tris(2-benzimidazolylmethyl)amine)-benzoato-copper(II) perchlorate monohydrate, CuC31H28N7O7Cl
  18. Crystal structure of [2-hydroxy-3-methyl-benzoato-k1 O-triphenyltin(IV)], C26H22O3Sn
  19. Crystal structure of diaqua-bis(4-(hydroxymethyl)-benzoato-k1 O)zinc(II), C16H18O8Zn
  20. The crystal structure of dicarbonyl-(N-nitroso-N-oxido-phenylamine-κ 2 O,O)-rhodium(I), C8H5N2O4Rh
  21. The crystal structure of oxalic acid – 2-ethoxybenzamide (2/1), C20H24N2O8
  22. The crystal structure of ethyl 7-ethyl-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate, C10H15N5O2
  23. Crystal structure of poly[(N,N-dimethylacetamide-κO) (μ4-2-nitroisophthalato-κ 4 O:O′:O″:O′″)manganese(II)], C11H10N2O7Mn
  24. Crystal structure of 14-O-acetyldelcosine, C26H41NO8
  25. The crystal structure of poly[(1,10-phenanthroline-κ2 N,N′)-(μ 4-2-chlorobenzene-1,3-dicarboxylato-κ5 O:O′:O″:O‴) cadmium(II)] monohydrate, C20H13CdClN2O5
  26. Crystal structure of propane-1,3-diylbis(diphenylphosphine sulfide) ethanol solvate, C27H26P2S2
  27. Crystal structure of bis{[(4-diethylamino-2-hydroxy-benzylidene)-hydrazinocarbonylmethyl]-trimethylammonium} tetrabromozincate, C32H54N8O4ZnBr4
  28. Synthesis and crystal structure of dimethyl 2,2′-(2,5-bis(4-hydroxyphenyl)-2,5-dihydrofuran-3,4-diyl)dibenzoate, C34H30O7
  29. Synthesis and crystal structure of 2-(2-oxo-2-phenylethyl)-4H-chromen-4-one, C17H12O3
  30. The crystal structure of tetra(imidazole-κ1 N)zinc(II) μ2-oxido-hexaoxido-divanadium(VI) C12H16N8O6V2Zn
  31. Crystal structure of S-2-(1-(5-methylpyridin-2-ylamino)octyl)-3-hydroxynaphthalene-1,4-dione, C24H28N2O3
  32. Crystal structure of bis(μ2-5-chloro-2-oxido-N-(1-oxido-2-oxo-2-phenylethylidene)-benzohydrazonato-κ5 N,O,O′:N′,O′′)-oktakis(pyridine-κ1 N)trinickel(II) – methanol – pyridine (1/1/1) C76H65N13Cl2Ni3O9
  33. The crystal structure of methyl 3,5-diaminobenzoate, C8H10N2O2
  34. Crystal structure of 10-(9H-carbazol-9-yl)-5H-dibenzo[a,d][7]annelen-5-one, C27H17NO
  35. Crystal structure of ethyl 1-(2-hydroxyethyl)-4-((4-methoxyphenyl)amino)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate, C16H20N2O5
  36. The crystal structure of 1-(4-bromophenyl)-3-cycloheptylurea, C14H19BrN2O
  37. The crystal structure of 1,4-bis(1,2,3,4,5-pentamethylcyclopenta-2,4-dien-1-yl)-3,6-bis ((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methylene)-1,4-dialuminacyclohexane – benzene (1/2), C50H72Al2B2O4
  38. Crystal structure of bis(μ 3-diphenylphosphinato)-tetrakis(μ 2-diphenylphosphinato)-bis(diphenylphosphinato)-bis(μ 2-hydroxo)dicopper(II)-ditin(IV), C104H100O18P8Cu2Sn2
  39. Crystal structure of 3-((3,4-dichloroisothiazol-5-yl)methoxy)benzo[d] isothiazole 1,1-dioxide, C11H6Cl2N2O3S2
  40. Synthesis and crystal structure of 2-(2-(2-fluorophenyl)-2-oxoethyl)-4H-chromen-4-one, C17H11FO3
  41. The crystal structure of tris(carbonyl)-bis(carbonyl)-[μ-propane-1,2- dithiolato]-(benzyldiphenylphosphine)diiron (Fe—Fe), C27H23Fe2O5PS2
  42. Crystal structure of 1-(2-(4-chlorophenethyl)-2-hydroxy-3,3-dimethylbutyl)-1H-1,2,4-triazol-4-ium nitrate, C16H23N4O4Cl
  43. The crystal structure of 3,3′-disulfanediyldi(1H-1,2,4-triazol-5-amine) monohydrate, C4H8N8OS2
  44. The crystal structure of trans-[bis(4-methylpyridine-κN)bis(quinoline-2-carboxylato- κ 2 N,O)cadmium(II)], C32H26CdN4O4
  45. The crystal structure of ethyl 2′-hydroxy-4′,6′-dimethoxy-3-(4-methoxynaphthalen-1-yl)-5-oxo-2,3,4,5-tetrahydro-[1,1′-biphenyl]-4-carboxylate, C28H28O7
https://doi.org/10.1515/ncrs-2022-0456
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Artikel in diesem Heft

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of undecacalcium decaarsenide, Ca11As10
  4. Crystal structure of catena-poly[diiodido-(μ2-1,5-dimethyl-2-phenyl-4-((pyridin-4- ylmethylene)amino)-1,2-dihydro-3H -pyrazol-3-one-κ2 N: O)zinc(II)], C17H16I2N4OZn
  5. The crystal structure of 5,10,15,20-tetrakis(4-(tert-butyl)phenyl)porphyrin-21,23-diido-κ4 N 4-naphthalocyanido-κ4 N 4-neodymium(IV) - chloroform (1/6) C114H90N12Cl18Nd
  6. The crystal structure of 1-(4-bromophenyl)-3-(2-chlorobenzyl)urea, C14H12BrClN2O
  7. Crystal structure of bis[benzyl(methyl)carbamodithioato-κ 2 S,S′]-di-n-butyltin(IV), C26H38N2S4Sn
  8. Crystal structure of (E)-3-(2-(4-(diethylamino)-2-hydroxystyryl)-3,3-dimethyl-3H-indol-1-ium-1-yl)propane-1-sulfonate – methanol (1/2), C25H32N2O4S⋅2CH3OH
  9. Synthesis and crystal structure of {(N′,N″-(((ethane-1,2-diylbis(oxy))bis(2,1-phenylene))-bis(methaneylylidene))bis(2-hydroxybenzohydrazonato)-κ6 N 2 O 4}copper(II), C30H24CuN4O6
  10. The crystal structure of ((E)-2,4-dibromo-6-(((5-(nitro)-2-oxidophenyl)imino)methyl)phenolato-κ 3 N,O,O′)tris(pyridine-κN)manganese(II), C28H21Br2MnN5O4
  11. Synthesis and crystal structure of 1-((3R,10S,13R,17S)-10,13-dimethyl-3-(p-tolylamino)hexadecahydro-1H-cyclopenta-[a]phenanthren-17-yl)ethan-1-one, C28H41NO
  12. The crystal structure of 3-nitrobenzene-1,2-dicarboxylic acid—pyrazine-2-carboxamide(1/1), C13H10N4O7
  13. Crystal structure of poly[tetrakis(μ3-2-aminonicotinato-κ3N,O,O′)-(μ2-oxalato-κ4 O,O′:O″,O′″)-(μ4-oxalato-κ6 N:N′:O,O′:O″,O′″)dicopper(I)-disamarium(III)], [SmCu(C6N2H5O2)2(C2O4)] n
  14. The crystal structure of 2,3,4-trihydroxybenzoic- acid—pyrazine-2-carboxamide—water (1/1/1), C12H13N3O7
  15. Crystal structure of N-ethyl-4-[3-(trifluoromethyl)-phenyl]piperazine-1-carbothioamide, C14H18F3N3S
  16. The crystal structure of 3-anilino-1,4-diphenyl-4H-1,2,4-triazol-1-ium iodide, C20H17N4I
  17. The crystal structure of (tris(2-benzimidazolylmethyl)amine)-benzoato-copper(II) perchlorate monohydrate, CuC31H28N7O7Cl
  18. Crystal structure of [2-hydroxy-3-methyl-benzoato-k1 O-triphenyltin(IV)], C26H22O3Sn
  19. Crystal structure of diaqua-bis(4-(hydroxymethyl)-benzoato-k1 O)zinc(II), C16H18O8Zn
  20. The crystal structure of dicarbonyl-(N-nitroso-N-oxido-phenylamine-κ 2 O,O)-rhodium(I), C8H5N2O4Rh
  21. The crystal structure of oxalic acid – 2-ethoxybenzamide (2/1), C20H24N2O8
  22. The crystal structure of ethyl 7-ethyl-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate, C10H15N5O2
  23. Crystal structure of poly[(N,N-dimethylacetamide-κO) (μ4-2-nitroisophthalato-κ 4 O:O′:O″:O′″)manganese(II)], C11H10N2O7Mn
  24. Crystal structure of 14-O-acetyldelcosine, C26H41NO8
  25. The crystal structure of poly[(1,10-phenanthroline-κ2 N,N′)-(μ 4-2-chlorobenzene-1,3-dicarboxylato-κ5 O:O′:O″:O‴) cadmium(II)] monohydrate, C20H13CdClN2O5
  26. Crystal structure of propane-1,3-diylbis(diphenylphosphine sulfide) ethanol solvate, C27H26P2S2
  27. Crystal structure of bis{[(4-diethylamino-2-hydroxy-benzylidene)-hydrazinocarbonylmethyl]-trimethylammonium} tetrabromozincate, C32H54N8O4ZnBr4
  28. Synthesis and crystal structure of dimethyl 2,2′-(2,5-bis(4-hydroxyphenyl)-2,5-dihydrofuran-3,4-diyl)dibenzoate, C34H30O7
  29. Synthesis and crystal structure of 2-(2-oxo-2-phenylethyl)-4H-chromen-4-one, C17H12O3
  30. The crystal structure of tetra(imidazole-κ1 N)zinc(II) μ2-oxido-hexaoxido-divanadium(VI) C12H16N8O6V2Zn
  31. Crystal structure of S-2-(1-(5-methylpyridin-2-ylamino)octyl)-3-hydroxynaphthalene-1,4-dione, C24H28N2O3
  32. Crystal structure of bis(μ2-5-chloro-2-oxido-N-(1-oxido-2-oxo-2-phenylethylidene)-benzohydrazonato-κ5 N,O,O′:N′,O′′)-oktakis(pyridine-κ1 N)trinickel(II) – methanol – pyridine (1/1/1) C76H65N13Cl2Ni3O9
  33. The crystal structure of methyl 3,5-diaminobenzoate, C8H10N2O2
  34. Crystal structure of 10-(9H-carbazol-9-yl)-5H-dibenzo[a,d][7]annelen-5-one, C27H17NO
  35. Crystal structure of ethyl 1-(2-hydroxyethyl)-4-((4-methoxyphenyl)amino)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate, C16H20N2O5
  36. The crystal structure of 1-(4-bromophenyl)-3-cycloheptylurea, C14H19BrN2O
  37. The crystal structure of 1,4-bis(1,2,3,4,5-pentamethylcyclopenta-2,4-dien-1-yl)-3,6-bis ((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methylene)-1,4-dialuminacyclohexane – benzene (1/2), C50H72Al2B2O4
  38. Crystal structure of bis(μ 3-diphenylphosphinato)-tetrakis(μ 2-diphenylphosphinato)-bis(diphenylphosphinato)-bis(μ 2-hydroxo)dicopper(II)-ditin(IV), C104H100O18P8Cu2Sn2
  39. Crystal structure of 3-((3,4-dichloroisothiazol-5-yl)methoxy)benzo[d] isothiazole 1,1-dioxide, C11H6Cl2N2O3S2
  40. Synthesis and crystal structure of 2-(2-(2-fluorophenyl)-2-oxoethyl)-4H-chromen-4-one, C17H11FO3
  41. The crystal structure of tris(carbonyl)-bis(carbonyl)-[μ-propane-1,2- dithiolato]-(benzyldiphenylphosphine)diiron (Fe—Fe), C27H23Fe2O5PS2
  42. Crystal structure of 1-(2-(4-chlorophenethyl)-2-hydroxy-3,3-dimethylbutyl)-1H-1,2,4-triazol-4-ium nitrate, C16H23N4O4Cl
  43. The crystal structure of 3,3′-disulfanediyldi(1H-1,2,4-triazol-5-amine) monohydrate, C4H8N8OS2
  44. The crystal structure of trans-[bis(4-methylpyridine-κN)bis(quinoline-2-carboxylato- κ 2 N,O)cadmium(II)], C32H26CdN4O4
  45. The crystal structure of ethyl 2′-hydroxy-4′,6′-dimethoxy-3-(4-methoxynaphthalen-1-yl)-5-oxo-2,3,4,5-tetrahydro-[1,1′-biphenyl]-4-carboxylate, C28H28O7
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Heruntergeladen am 22.9.2025 von https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2022-0456/html
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