Startseite The crystal structure of 2,3-di(pyridin-2-yl)-2,3-dihydroquinazolin-4(1H)-one, C18H14N4O
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The crystal structure of 2,3-di(pyridin-2-yl)-2,3-dihydroquinazolin-4(1H)-one, C18H14N4O

  • Sheng-Jie Liu , Ying Zhang , Lin Yuan ORCID logo EMAIL logo und Xiao-Ming Chen EMAIL logo
Veröffentlicht/Copyright: 1. Oktober 2024

Abstract

C18H14N4O, orthorhombic, Pbca (no. 61), a = 7.963(3) Å, b = 12.629(5) Å, c = 30.116(11) Å, V = 3,028.3(19) Å3, Z = 8, R gt (F) = 0.0475, wR ref (F 2) = 0.1444, T = 296(2) K.

CCDC no.: 2384585

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: 0.50 × 0.43 × 0.36 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.09 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θ max, completeness: 25.0°, >99 %
N(hkl)measured, N(hkl)unique, R int: 25,773, 2,670, 0.030
Criterion for I obs, N(hkl)gt: I obs >2 σ(I obs), 2184
N(param) refined: 208
Programs: Bruker 1 , SHELX 2 , 3
Table 2:

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

Atom x y z U iso*/U eq
C1 0.1223 (2) 0.78869 (15) 0.30912 (6) 0.0543 (5)
C2 0.0655 (3) 0.71410 (19) 0.27878 (8) 0.0733 (6)
H2 0.0368 0.6466 0.2885 0.088*
C3 0.0515 (4) 0.7390 (3) 0.23482 (9) 0.0985 (9)
H3 0.0108 0.6894 0.2147 0.118*
C4 0.0981 (4) 0.8386 (3) 0.22044 (9) 0.1065 (11)
H4 0.0926 0.8546 0.1903 0.128*
C5 0.1525 (3) 0.9146 (2) 0.24983 (9) 0.0840 (7)
H5 0.1842 0.9812 0.2397 0.101*
C6 0.1598 (2) 0.89094 (17) 0.29489 (7) 0.0585 (5)
C7 0.1639 (2) 0.75471 (14) 0.35500 (7) 0.0513 (5)
C8 0.2610 (2) 0.81737 (15) 0.42827 (6) 0.0516 (5)
C9 0.3257 (3) 0.72266 (19) 0.44397 (8) 0.0741 (6)
H9 0.3312 0.6632 0.4258 0.089*
C10 0.3818 (4) 0.7191 (2) 0.48725 (9) 0.0882 (8)
H10 0.4251 0.6564 0.4987 0.106*
C11 0.3740 (4) 0.8065 (3) 0.51299 (9) 0.0927 (8)
H11 0.4122 0.8052 0.5422 0.111*
C12 0.3094 (4) 0.8955 (2) 0.49527 (9) 0.0939 (9)
H12 0.3049 0.9557 0.5130 0.113*
C13 0.1542 (2) 0.94176 (13) 0.37130 (6) 0.0458 (4)
H13 0.2131 0.9915 0.3909 0.055*
C14 −0.0339 (2) 0.95845 (13) 0.37785 (5) 0.0457 (4)
C15 −0.1002 (3) 1.05442 (15) 0.36609 (7) 0.0644 (5)
H15 −0.0333 1.1069 0.3535 0.077*
C16 −0.2692 (3) 1.0711 (2) 0.37341 (9) 0.0815 (7)
H16 −0.3178 1.1356 0.3660 0.098*
C17 −0.3647 (3) 0.9927 (2) 0.39158 (8) 0.0800 (7)
H17 −0.4791 1.0026 0.3963 0.096*
C18 −0.2906 (3) 0.9009 (2) 0.40257 (8) 0.0783 (7)
H18 −0.3563 0.8481 0.4153 0.094*
N1 0.2079 (2) 0.96241 (13) 0.32681 (6) 0.0626 (5)
H1 0.2675 1.0171 0.3204 0.075*
N2 0.20569 (19) 0.83406 (11) 0.38396 (5) 0.0477 (4)
N3 0.2513 (3) 0.90276 (14) 0.45360 (6) 0.0722 (5)
N4 −0.1254 (2) 0.88098 (14) 0.39609 (6) 0.0650 (5)
O1 0.1694 (2) 0.66070 (10) 0.36501 (5) 0.0731 (5)

1 Source of material

2-Amino-N-(pyridin-2-yl)benzamide (213.24 mg, 1 mmol) and pyridine-2-carboxaldehyde (107.11 mg, 1 mmol) were dissolved in ethanol (10 mL) and the mixture was refluxed for 4 h. The reaction mixture was concentrated in vacuum, and the title compound was isolated through a silica gel column chromatography (PE: EtOAc = 3:1) as a white solid (120.64 mg, 40 % yield). Single crystals of the product can be obtained by recrystallization in ethanol through slow evaporation within 3 days.

2 Experimental details

All hydrogen atoms were identified in difference Fourier syntheses. The U iso values of all hydrogen atoms were set to 1.2U eq (C).

3 Comment

2,3-Dihydroquinazolin-4(1H)-ones are components of many bioactive molecules with broad-spectrum pharmacological properties, such as anti-malaria, anti-cancer, anti-microbial, anti-hypertension, anti-oxidation, anti-inflammatory and so on. 4 , 5 , 6 , 7 , 8

The crystal structure reveals that the title molecule is non-planar. Plane I (C1–C6) forms a dihedral angle of 35.443(8)° with plane II (C8–N3), and 86.885(7)° with plane III (C14–N4). The dihedral angle between plane II and plane III is 89.799(9). The C(13) atom is sp3 hybridized and R-type chiral carbon. The bond lengths of O(1)–C(7) and C(1)–C(7) are 1.226(2) Å and 1.484(3) Å. The sp3 C(13)–N(1), C(13)–N(2) bond lengths are 1.430(2) Å, 1.471(2) Å, which are longer than the sp2 C(7)–N(2), C(8)–N(2), C(6)–N(1), C(14)–N(4), C(18)–N(4), C(8)–N(3), C(12)–N(3) bond lengths of 1.369(2) Å, 1.421(2) Å, 1.373(3) Å, 1.337(2) Å, 1.354(3) Å, 1.323(3) Å, 1.341(3) Å, respectively. The bond angles of O(1)–C(7)–C(1), O(1)–C(7)–N(2), C(1)–C(7)–N(2), C(6)–N(1)–C(13), C(8)–N(3)–C(12), C(14)–N(4)–C(18), N(2)–C(13)–N(1), N(1)–C(13)–C(14) and N(2)–C(13)–C(14) are 121.13(17)°, 122.92(18)°, 115.82(16)°, 116.92(16)°, 117.6(2)°, 116.91(19)°, 109.16(14)°, 112.91(15)° and 111.59(14)°, respectively. Geometric parameters are all in the expected ranges. 6 , 9


Corresponding authors: Lin Yuan and Xiao-Ming Chen, College of Chemistry and Bioengineering, Hunan University of Science and Engineering, Yongzhou, Hunan, 425199, P.R. China, E-mail: (L. Yuan), (X.-M. Chen)

  1. Research funding: This work was financially supported by Natural Science Foundation of Hunan Province of China (2024JJ7198), the Scientific Research Fund of Hunan Provincial Education Department (21A0518, 23B0751).

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

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

References

1. Bruker. APEX3, SAINT–Plus, XPREP; Bruker AXS Inc.: Madison, Wisconsin, USA, 2016.Suche in Google Scholar

2. Sheldrick, G. M. SHELXT – Integrated Space-Group and Crystal-Structure Determination. Acta Crystallogr. 2015, A71, 3–8; https://doi.org/10.1107/s2053273314026370.Suche in Google Scholar PubMed PubMed Central

3. Sheldrick, G. M. Crystal Structure Refinement with SHELXL. Acta Crystallogr. 2015, C71, 3–8; https://doi.org/10.1107/s2053229614024218.Suche in Google Scholar

4. Shi, D.; Li, Z.; Shi, C.; Zhuang, Q.; Zhang, Y. 3-(4-Bromo-phenyl)-2,2-Di-Methyl-2,3-Di-Hydro-Quinazolin-4(1H)-One. Acta Crystallogr. 2004, E60, 1992–1994; https://doi.org/10.1107/s1600536804025115.Suche in Google Scholar

5. Shi, D.; Wang, J.; Rong, L.; Wang, X.; Hu, H. 2,2-Di-Methyl-3-(4-Methyl-Phenyl)-1,2-Di-Hydro-Quinazolin-4(3H)-One. Acta Crystallogr. 2003, E59, 1689–1690; https://doi.org/10.1107/s1600536803022128.Suche in Google Scholar

6. Lu, Z. S.; Wang, X. S.; Zhu, G. Z.; Li, X. L.; Niu, D. Z. Crystal Structure of 2,3-Dihydro-2-Phenyl-3-[(E)-(1- Phyenylethylidene)amino]-4(1H)-Quinazolinone, C22H19N3O. Z. Kristallogr. N. Cryst. Struct. 2012, 227, 499–500.10.1524/ncrs.2012.0237Suche in Google Scholar

7. Jain, S. C.; Bharadvaja, A.; Kumar, R.; Agarwal, D.; Errington, W. 3-[4-(3,4-Dimethylphenyl)-1,3-Thiazol-2-yl]-2-(2-hydroxyphenyl)-1,2,3,4-Tetrahydroquinazolin-4-One. Acta Crystallogr. 2000, C56, 592–593; https://doi.org/10.1107/s0108768100001816.Suche in Google Scholar

8. Memarian, H. R.; Ebrahimi, S.; Rudbari, H. A.; Sabzyan, H.; Nardo, V. M. Inter- and Intramolecular Interactions in 2,3-Dihydroquinazolin-4(1H)-Ones: Molecular Structure and Conformational Analysis. J. Iran. Chem. Soc. 2016, 13, 1395–1404.10.1007/s13738-016-0854-6Suche in Google Scholar

9. Baykova, S. O.; Geyl, K. K.; Baykov, S. V.; Boyarskiy, V. P. Synthesis of 3-(Pyridin-2-yl)Quinazolin-2,4(1H,3H)-Diones Via Annulation of Anthranilic Esters with N-Pyridyl Ureas. Int. J. Mol. Sci. 2023, 24, 7633.10.3390/ijms24087633Suche in Google Scholar PubMed PubMed Central

Received: 2024-06-22
Accepted: 2024-09-17
Published Online: 2024-10-01
Published in Print: 2024-12-17

© 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. Crystal structure of 3-nitrophenol-2,1,3-benzoselenadiazole (1/1), C12H9N3O3Se
  4. Crystal structure of diaqua-(hydroxido)-{μ-[2-(hydroxy)-5-[(4-nitrophenyl)diazenyl]benzoato]}-{2-hydroxy-5-[(4-nitrophenyl)diazenyl]benzoato}-(1,10-phenanthroline)-diterbium hydrate, C38H27.4N8O12.2Tb
  5. Crystal structure of poly[bis(μ3-3-fluoro-4-(1H-1,2,4-triazol-1-yl)benzoato-κ3 O:O′:N)cadmium(II)] – dimethylformamide (1/1), C21H17CdF2N7O5
  6. The crystal structure of 2-amino-N-(pyridin-2-yl)benzamide, C12H11N3O
  7. The crystal structure of 2,3-di(pyridin-2-yl)-2,3-dihydroquinazolin-4(1H)-one, C18H14N4O
  8. Crystal structure of 2-chloro-4-fluorobenzyl (R)-2-(6-methoxynaphthalen-2-yl)propanoate, C21H18ClFO3
  9. Crystal structure of [1-(4-carboxyphenyl)-4-oxo-1,4-dihydropyridazine-3-carboxylic acid]-(methylsulfinyl)methane, C15H16N2O6S
  10. The crystal structure of 2-ethyl-1,1-dimethyl-1H-benzo[e]indole, C16H17N
  11. The crystal structure of (Z)-5-amino-N -hydroxy-1H-pyrazole-4-carboximidamide, C4H7N5O
  12. The crystal structure of 2,2,5-trimethyl-3-(4-(4-(5-phenyl-4,5-dihydroisoxazol-3-yl)thiazol-2-yl)phenyl)imidazolidin-4-one, C24H24N4O2S
  13. The crystal structure of tetrakis(μ2-acetato-κ2 O:O′)-bis[(4′-phenyl-4,2′:6′,4″-terpyridine-κ1 N)dicopper(II)], C25H21CuN3O4
  14. Crystal structure of poly(3-thiophenecarboxylato-κ 3 O,O′:O′)-(methanol-κO)cadmium(II), C11H10O5S2Cd
  15. The crystal structure of dichloridobis[4′-(p-methoxylphenyl)-4,2′:6′,4″-terpyridine-κN] zinc(II), C44H34Cl2N6O2Zn
  16. The crystal structure of 1-(2-carboxyethyl)-1H-imidazole 3-oxide
  17. Crystal structure of 1,1′,1″-(nitrilotris(ethane-2,1-diyl))tris(3-(4-(((E)-pyridin-2-ylmethylene)amino)phenyl)urea), C45H47N13O4
  18. Crystal structure of a (E)-4-bromo-N-(4-(diethylamino)-2-hydroxybenzylidene) benzenaminium acetate ─ 4-bromoaniline (1/1)
  19. Crystal structure of 2,2′-(iminobis(methylene))bis(benzimidazolium) bis(p-toluenesulfonate), C30H31N5O6S2
  20. The crystal structure of alogliptinium meta-chlorobenzoate
  21. Crystal structure of 4-bromobenzyl 2-(6-methoxy-naphthalen-2-yl)propanoate, C21H19BrO3
  22. The hydrated double salt structure of (E)-4-(2-benzylidenehydrazine-1-carbonyl)pyridin-1-ium cation with 2-hydroxybenzoate and benzoate anions
  23. Crystal structure of (R)(R)-5-chloro-3-((S,1E,3E)-3,5-dimethyl-hepta-1,3-dien-1-yl)-7-methyl-6,8-dioxo-2,6,7,8-tetrahydroisoquinolin-7-yl acetate, C21H24ClNO4
  24. The crystal structure of bis(3-oxo-1,3-diphenylprop-1-en-1-olato-κ 2 O:O′)-bis(1,4-dioxane-κ 1 O)nickel(II), C38H38O8Ni
  25. Crystal structure of poly[aqua-(pyridine-3-carboxylato-κ1 N)(pyridine-3-carboxylato-κ2 O,O′) cadmium(II)] dihydrate, C12H14N2O7Cd
  26. The crystal structure of 4-(4-phenyl-5-(((1-(2,4,6-tribromophenyl)-1H-1,2,3-triazol-4-yl)methyl)thio)-4H-1,2,4-triazol-3-yl)pyridine, C22H14Br3N7S
  27. The crystal structure of N-benzylquinoline-2-carbothioamide, C17H14N2S
  28. Crystal structure of bis(3-isopropylphenyl)-4,4′-bipyridinium dichloride dihydrate, C28H30N2⋅2Cl⋅2H2O
  29. The crystal structure of ethyl 2-amino-4-(cyanophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate, C19H18N2O4
  30. Crystal structure of (4R,10S)-6-hydroxy-7-isopropyl-4,10-dimethyl-1,2,3,5-hexahydro-6,10-epoxyazulen-9-one, C15H22O3
  31. The crystal structure of (E)-(2-(2-hydroxy-3-methoxybenzylidene)aminophenyl)arsonic acid, C14H14AsNO5
  32. The crystal structure of poly[(μ 2-2-aminoisophthalato-κ4O,O′:O″:O″′)-(N-methylpyrrolidone κ1O)-dioxido-uranium(VI)], C13H14N2O7U
  33. The crystal structure of the co-crystal isonicotinamide · terephthalic acid, C8H6O4·2(C6H6N2O)
  34. The crystal structure of (E)-1-phenyl-3-(p-tolylthio)but-2-en-1-one, C17H16OS
  35. The crystal structure of 4,5-bis((Z)-chloro(hydroxyimino)methyl)-1H-imidazol-3-ium chloride monohydrate
  36. The crystal structure of 1,2-bis(4-(dimethylamino)phenyl)ethane-1,2-dione. C18H20N2O2
  37. Crystal structure of 2-chloro-4-fluorobenzyl 2-acetoxybenzoate, C16H12ClFO4
  38. Crystal structure of methyl 1-phenyl-9H-pyrido[3,4-b]indole-3-carboxylate, C19H14N2O2
  39. Crystal structure of (3-(dimethoxymethyl)-5-methoxy-1H-indol-1-yl)(5-fluoro-2-iodophenyl)methanone, C19H17FINO4
  40. Crystal structure of tetrachlorido-bis(1-[(1H-triazole-1-yl)methyl]-1H-benzotriazole-κ2 N:N′)dicopper, C36H32Cu2N24Cl4
  41. Crystal structure of 2-(2,3-bis(4-methoxyphenyl)-1H-pyrrolo[2,3-b]quinoxalin-1-yl)anilin, C30H24N4O2
  42. Crystal structure of 5,7-dihydroxy-2-phenyl-4H-chromen-4-one–N,N-dimethylformamide(1/1), C18H17NO5
  43. The crystal structure of bis(μ 2-biphenyl-2,2′-dicarboxylato)-diaqua-bis(nitrato)-bis(2,2′:6′,2′′-terpyridine)dineodymium(III), C46H32I2N8Nd2O16
  44. Crystal structure of (Z)-4-amino-N -((4-chlorophenyl)(phenyl)methylene)benzohydrazide, C20H16ClN3O
  45. Crystal structure of (E)-6,8-dimethoxy-4-(4-morpholinobenzylidene)-3,4-dihydro-1-benzoxepin-5(2H)-one, C23H25NO5
  46. Crystal structure of (R)-2-((3-(3-aminopiperidin-1-yl)-6-methyl-5-oxo-1,2,4-triazin-4(5H)-yl) methyl)-4-fluorobenzonitrile benzoate monohydrate, C24H27FN6O4
  47. The crystal structure of [triaqua-(8-carboxymethoxy-quinoline-2-carboxylato-κ 3 N,O,O)copper(II)]monohydrate, C12H15NO9Cu
  48. Crystal structure of (((4-chlorophenyl)sulfonyl)glycinato-κ 2 N,O)bis(1,10-phenanthroline-κ 2 N,N′)cobalt(II) tetrahydrate, C32H30ClCoN5O8S
  49. Crystal structure of (((3-nitrophenyl)sulfonyl)-β-alaninato-κO)bis(2,2′-bipyridine-κ 2 N, N′)copper(II) 3-nitrobenzenesulfonate, C35H29CuN7O11S2
  50. Crystal structure of 3-phenoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C27H24O4
  51. 6-(2′,3′-Dihydroxy-3′-methylbutyl)-7-methoxy-8-(3″-methylbut-2″-en-1″-yl)-2H-chromen-2-one, C20H26O5
  52. Crystal structure of bromido-(2,2′:6′,2″-terpyridine-4′-onato-κ3N)palladium(II) methanol solvate
  53. The crystal structure of ethyl 2-amino-(4-nitrophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate, C20H22N2O6
  54. Crystal structure of (1E,3E,5E)-1,6-bis(4-(pentyloxy)phenyl)hexa-1,3,5-triene, C28H36O2
  55. The crystal structure of tris(2-bromo-4-methylphenyl)amine, C21H18Br3N
  56. The crystal structure of 3-(2,5-dimethylanilino)-1-(2,5-dimethylphenyl)-4-methyl-1H-pyrrole-2,5-dione, C21H22N2O2
  57. Crystal structure of dicarbonyl (μ2-indole-2-carboxylato κ2 O:O′)tris(triphenylarsine-κAs)dirhodium(I) acetone solvate, C68H56As3NO5Rh2
  58. The crystal structure of 4-chloro-2-formylphenyl 4-methylbenzenesulfonate, C14H11ClO4S
  59. Crystal structure of 4-iodobenzyl 2-(6-methoxynaphthalen-2-yl) propanoate, C21H19IO3
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