Home Crystal structure of 2-(5-phenyl-1-(quinolin-2-yl)-4,5-dihydro-1H-pyrazol-3-yl)phenol, C24H19N3O
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Crystal structure of 2-(5-phenyl-1-(quinolin-2-yl)-4,5-dihydro-1H-pyrazol-3-yl)phenol, C24H19N3O

  • Dai Zeng , Kai Tan , Ziyan Fang and Aiping Xing ORCID logo EMAIL logo
Published/Copyright: September 15, 2023
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 238 Issue 6

Abstract

C24H19N3O, monoclinic, P21/c (no. 14), a = 10.4783(5) Å, b = 11.7171(5) Å, c = 14.9194(6) Å, β = 93.991(2)°, Z = 4, V = 1827.29(14) Å3, Rgt(F) = 0.0521, wR ref (F2) = 0.1508, T = 150(2) K.

CCDC no.: 2288022

The asymmetric unit of 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: Yellow block
Size: 0.21 × 0.21 × 0.20 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.08 mm−1
Diffractometer, scan mode: Bruker APEX II, ω
θmax, completeness: 27.5°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 16,737, 4165, 0.058
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 3391
N(param)refined: 254
Programs: Bruker [1], SHELX [2], [3], [4]
Table 2:

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

Atom x y z Uiso*/Ueq
C1 0.03398 (15) −0.07204 (13) 0.67616 (9) 0.0363 (3)
H1 0.062716 −0.148579 0.683588 0.044*
C2 −0.06060 (15) −0.03185 (15) 0.72672 (10) 0.0413 (4)
H2 −0.096828 −0.080328 0.769236 0.050*
C3 −0.10401 (15) 0.08103 (15) 0.71570 (10) 0.0404 (4)
H3 −0.170155 0.108159 0.750592 0.049*
C4 −0.05199 (14) 0.15283 (14) 0.65503 (9) 0.0340 (3)
H4 −0.082184 0.229043 0.648630 0.041*
C5 0.04618 (13) 0.11395 (12) 0.60210 (8) 0.0274 (3)
C6 0.08931 (13) −0.00042 (12) 0.61288 (8) 0.0287 (3)
C7 0.18571 (13) −0.03735 (11) 0.55713 (9) 0.0294 (3)
H7 0.216026 −0.113715 0.561185 0.035*
C8 0.23475 (13) 0.03607 (11) 0.49802 (9) 0.0272 (3)
H8 0.299106 0.012112 0.460326 0.033*
C9 0.18704 (12) 0.15010 (11) 0.49406 (8) 0.0248 (3)
C10 0.17755 (13) 0.33883 (11) 0.41141 (8) 0.0273 (3)
H10 0.082264 0.331514 0.405260 0.033*
C11 0.22931 (13) 0.35856 (12) 0.31828 (9) 0.0303 (3)
H11A 0.162265 0.344883 0.269386 0.036*
H11B 0.263078 0.436977 0.312805 0.036*
C12 0.33452 (12) 0.27128 (11) 0.31697 (8) 0.0248 (3)
C13 0.42898 (12) 0.26678 (11) 0.25005 (9) 0.0261 (3)
C14 0.53215 (13) 0.18893 (12) 0.25635 (10) 0.0329 (3)
C15 0.62124 (14) 0.18941 (13) 0.19190 (12) 0.0409 (4)
H15 0.691157 0.137646 0.196868 0.049*
C16 0.60912 (14) 0.26466 (13) 0.12044 (11) 0.0386 (4)
H16 0.670182 0.263616 0.076270 0.046*
C17 0.50872 (14) 0.34143 (13) 0.11281 (10) 0.0350 (3)
H17 0.500725 0.392986 0.063596 0.042*
C18 0.41994 (13) 0.34274 (12) 0.17732 (9) 0.0299 (3)
H18 0.351585 0.396124 0.172185 0.036*
C19 0.21608 (12) 0.43379 (11) 0.47688 (8) 0.0259 (3)
C20 0.32214 (15) 0.42667 (13) 0.53781 (10) 0.0370 (3)
H20 0.370847 0.358272 0.542364 0.044*
C21 0.35727 (16) 0.51964 (14) 0.59228 (11) 0.0426 (4)
H21 0.430532 0.514630 0.633336 0.051*
C22 0.28623 (15) 0.61915 (13) 0.58699 (10) 0.0367 (3)
H22 0.310240 0.682138 0.624555 0.044*
C23 0.17973 (14) 0.62663 (12) 0.52661 (10) 0.0330 (3)
H23 0.130452 0.694733 0.522873 0.040*
C24 0.14526 (13) 0.53458 (11) 0.47169 (9) 0.0287 (3)
H24 0.072643 0.540280 0.430111 0.034*
N1 0.09585 (10) 0.18889 (9) 0.54289 (7) 0.0268 (3)
N2 0.23597 (11) 0.22764 (9) 0.43640 (7) 0.0279 (3)
N3 0.33205 (10) 0.19781 (9) 0.38185 (7) 0.0263 (3)
O1 0.54848 (11) 0.11343 (10) 0.32507 (9) 0.0489 (3)
H1A 0.486348 0.117934 0.357564 0.073*

1 Source of materials

All chemicals were of reagent grade and used without further purification. The title compound was prepared following a literature procedure [5].

The intermediate is synthesized through aldol condensation reaction. 2-Hydroxy acetophenone (5.25 mmol) and benzaldehyde (5 mmol) were added to a 100 mL round-bottom flask along with 20 mL ethanol (EtOH). The mixture was stirred at room temperature for 10 min. An aqueous solution (2 mL) of NaOH (5 mmol) was then added drop wise. Subsequently, the mixture was agitated and allowed to stand at room temperature for additional 10 h. After completion, the reaction mixture was poured into ice cold water and neutralized with diluted HCl. Finally, the precipitated solid was filtered, washed with excess of cold water, dried and then recrystallized from ethanol to obtain the 2′-hydroxychalcone as yellow crystals. Yield: ca. 86 %.

The second step of synthetic procedure is as follows: A mixture of 2′-hydroxychalcone (10 mmol) and 2-hydrazinoquinoline (10 mmol) was dissolved in ethanol (30 ml) containing sodium hydroxide (30 mmol) and then refluxed for 4 h on an oil-bath. Completion of the reaction was confirmed by TLC. Five milliliter H2O were added and the reaction mixture was further stirred for 5 min. The above mixture was neutralized with diluted HCl. The orange yellow precipitates were isolated by filtration and recrystallized from ethanol. Yield: ca. 81 %. Suitable crystals of the title compound were grown from the mixed solution of ethanol and DMF by slow evaporation at room temperature.

2 Experimental details

The H atoms were added using riding models. Their Uiso values were set to 1.2Ueq of the parent atoms.

3 Comment

The construction of 1,3,5-trisubstituted pyrazolines has attracted great attention in recent years due to their wide applications in pharmaceuticals, fluorescent probes and electroluminescent materials [6], [7], [8], [9], [10]. In view of the structural diversity and important significance of 1,3,5-trisubstituted pyrazolines, research involving single crystal structures is of great significance to reveal the structure-activity relationship. The title compound 2-(5-phenyl-1-(quinolin-2-yl)-4,5-dihydro-1H-pyrazol-3-yl)phenol bearing both pyrazoline and quinoline moieties belongs to an important kind of 1, 3, 5-trisubstituted pyrazoline compounds.

The title compound crystallizes in the monoclinic space group P21/c with one molecule in the asymmetric unit (see the Figure). Bond lengths and angles are all in the normal range. A pyrazoline group as the five-membered core ring is formed by addition cyclization reaction of chalcone and hydrazine. The bond length of C12–N3 (1.2970 Å) indicates the existence of C=N in the pyrazoline ring, which is typical for similar compounds [11], [12], [13]. The pyrazoline ring is close to being planar with the largest deviation from the mean plane being 0.0883° for atom C10. In addition to the pyrazoline ring, it is substituted by a quinoline group, and a phenyl group and a phenol-2-yl group. The pyrazoline ring makes dihedral angles of 9.9° and 19.2° with the phenol and quinoline rings, respectively. Due to the steric hindrance effect, the benzene ring is almost perpendicular to the attached pyrazoline ring, showing a dihedral angle of approximately 103.9°. Phenolic hydroxyl group forms an intramolecular hydrogen bond to the pyrazoline N3 atom [O1⋯N3: 2.6656(16) Å]. π⋯π interactions are observed for parallel quinoline rings with the centroid-centroid distance between the two pyridine moieties of 3.66 Å.

Corresponding author: Aiping Xing, Henan University of Chinese Medicine, Zhengzhou 450046, P.R. China, E-mail:

Funding source: Zhongjing Scholars Research Funding of Henan University of Chinese Medicine

Award Identifier / Grant number: 00104311–2023–50

  1. Research ethics: This study did not involve any animal experiments.

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

  3. Competing interests: The authors declare no conflicts of interest regarding this article.

  4. Research funding: This work was supported by the Zhongjing Scholars Research Funding of Henan University of Chinese Medicine (00104311–2023–50).

  5. Data availability: All relevent data are within the paper.

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Received: 2023-08-16
Accepted: 2023-08-30
Published Online: 2023-09-15
Published in Print: 2023-12-15

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

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

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https://doi.org/10.1515/ncrs-2023-0372
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of bis(dimethylammonium) poly[(μ4-1,1′-(1,4-phenylenebis(methylene))bis(1H-pyrazole-3,5-dicarboxylato))-κ6O1, N2:O2:O3:O1′,N2′]nickel (II)], C22H26N6NiO8
  4. Hydrothermal synthesis and crystal structure of catena-poly[diaqua-bis(μ2-4-((pyridin-4-ylmethyl)amino)benzoato-κ2N:O)cobalt(II)] – 4,4′-bipyridine – water (1/2/2)
  5. Crystal structure of (2S,3S,4S,5S, Z)-2,3,5,6-tetrakis(benzyloxy)-4-hydroxyhexanal oxime, C34H37NO6
  6. The crystal structure of hexakis(3-thiophenecarboxylato-κ2O,O″)-bis(1,10-phenanthroline-κ2N,N′) trimanganese(II), C54H34N4O12S6Mn3
  7. Crystal structure of catena-poly[(μ2-1,4-di(pyridin-4-yl)benzene-κ2N:N′)-(4-bromobenzoate-κ2O:O′)-(μ-2-bromobenzoate-κ2O,O′)nickel(II)] – water (2/1), C30H21Br2N2NiO4.5
  8. The crystal structure of poly[(μ3-1,3-phenylenedioxydiacetate-κ5O,O,O′,O″,O‴)-bis(4′-(4-(1H-imidazol-1-yl)phenyl)-4,2′:6′,4″-terpyridine-kN) cadmium(II)], C58H42CdN10O6
  9. The crystal structure of 5-chloro-6′-methyl-3-(4-(methylsulfonyl)phenyl)-[2,3′-bipyridin]-1′-ium 4-methylbenzenesulfonate
  10. Crystal structure of poly[(μ-benzoato)-(μ-cis-4–hydroxy-D-proline)lithium], C12H14LiNO5
  11. The crystal structure of catena-poly[aqua-(4-iodopyridine-2,6-dicarboxylato-κ3N,O,O′)-copper(II)] monohydrate, C7H6NO6ICu
  12. The crystal structure of catena-[diaqua-(4-acetylphenoxyacetato-κ2O,O)-bis(4-acetylphenoxyacetato-κ3O,O:O)-dihydrate-lanthanum(III)]–4,4′-bipyridine (2/1), C35H35NO14La
  13. The crystal structure of catena-poly[(4-iodopyridine-2,6-dicarboxylato-κ4 O,N,O′,O′′)(4-imidazol-1-yl-pyridine-κN)copper(II)], C15H9N4O4ICu
  14. Crystal structure of polybis(μ 4-3,5-dicarboxylatopyrazol-1-yl)-bis(N,N-dimethylformamide)tri-copper(II)–acetonitrile (1/2), C20H22Cu3N8O10
  15. Crystal structure of poly[(μ2-5-hydroxy-isophthalato-κ4O,O′:O″,O‴)-(μ2-1,5-bis(imidazol-2-methyl)pentane-κ2N:N′)cadmium(II)], C21H24CdN4O5
  16. The crystal structure of poly[bis(μ2-1,4-bi(1-imidazolyl)benzene-κ2N:N′)bis(μ2-4,4′-methylenebis(3-hydroxy-2-naphthoate)-κ2O:O′)cobalt(II)], C35H24CoN4O6
  17. The crystal structure of a cobalt-vanadium-oxido hydrate
  18. The crystal structure of catena-poly[(μ 2-2H-1,2,3-triazole-4,5-dicarboxylato-κ 2 O, O′)-(μ 2-1,3-bis((1H-imidazol-1-yl)methyl)benzene-κ 2 N,N′) zinc(II)], C18H15N7O4Zn
  19. Crystal structure of poly[diaqua-(bis(m2-1,4-bis(imidazol-1-ylmethyl)benzene)-κ2N,N′-manganese] dichloride, C28H32MnN8O2Cl2
  20. The crystal structure of 9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino [3,2-a]isoquinolin-7-ium (E)-3-(4-nitrophenyl)acrylate pentahydrate, C29H34N2O13
  21. Crystal structure of poly[(μ6-ammoniotris(methylene))tris(hydrogen phosphonato)cadmium(II)], C3H10CdNO9P3
  22. Crystal structure of Zn2[(1,1′-(hexane-1,6-diyl)bis(3-(pyridin-3-yl)urea))·(H2O)2·(DMF)2·(SO4)2], C24H50N8O18S2Zn2
  23. The crystal structure of 2-anilino-1,4-naphthoquinone, C10H11NO2
  24. Crystal structure of (E)-2-(2-(4-(diethylamino)styryl)-1-ethyl-1,4-dihydroquinolin-4-yl) malononitrile, C26H26N4
  25. Crystal structure of ethyl 2-((2,6-dichloro-4-(cyanomethyl)phenyl) amino)benzoate, C17H14Cl2N2O2
  26. Synthesis and crystal structure of 2-(3-oxo-3-phenylpropyl)isoindoline-1,3-dione, C17H13NO3
  27. The crystal structure of bis(acetonitrile-κ1N)tetrakis(μ2-2,6-difluorobenzoato-κ2O:O′)rhodium(II) (Rh–Rh), C32H18F8O8N2Rh2
  28. The crystal structure of a new polymorph of 6-hydroxy-2-naphthoic acid, C11H8O3
  29. The crystal structure of [(8-carboxymethoxy-quinoline-2-carboxylate-κ4N,O,O,O)-2,2′-bipyridine-κ2N-copper(II)] tetrahydrate, C22H23N3O9Cu
  30. The crystal structure of ethyl 4-hydroxy-2-(4-methoxyphenyl)-5-oxo-1-(2-oxo-2H-chromen-6-yl)-2,5-dihydro-1H-pyrrole-3-carboxylate, C23H19NO7
  31. Crystal structure of 7-hydroxy-3,4-dihydronaphthalen-1(2H)-one, C10H10O2
  32. Crystal structure of bis(tetrapropylammonium) dodecacarbonyltetratelluridotetraferrate(2-), (Pr4N)2[Fe4Te4(CO)12]
  33. The crystal structure of poly[bis(μ2−3−aminopyridine−4−carboxylato−κ2N:O)Zinc(II)], [Zn(C6H5N2O2)2] n
  34. The crystal structure of methyl 5-nitro-2-(tosyloxy)benzoate, C15H13NO7S
  35. The crystal structure of 18-crown-6 ― tetraaqua-dichlorido-di-μ2-chloridodicopper(II) (2/1), C12H32O10Cu2Cl4
  36. Crystal structure of 6,6a,7,8,9,10-hexahydro-5H-pyrazino [2,3-e]pyrido[1,2-a]pyrazine, C10H14N4
  37. Crystal structure of catena-poly-{diaqua-bis[μ-(((4-chlorophenyl)sulfonyl)glycinato-κO)](μ2-4, 4′-bipyridine-κ2N:N′)cobalt(II)} dihydrate, C26H30Cl2CoN4O12S2
  38. Crystal structure of bis{N′-[1,3-diphenylprop-2-en-1-ylidene]-N-phenylcarbamohydrazonothioato}zinc(II), C44H36N6S2Zn
  39. Crystal structure of tetraaqua-bis(((4-chlorophenyl)sulfonyl)glycinato-κO)cobalt(II) dihydrate, C16H26Cl2CoN2O14S2
  40. Crystal structure of 2-(5-phenyl-1-(quinolin-2-yl)-4,5-dihydro-1H-pyrazol-3-yl)phenol, C24H19N3O
  41. Crystal structure of 2-((2-fluoro-4-(trifluoromethyl)phenyl)(hydroxy)methyl)-7-methoxy-3,4-dihydronaphthalen-1((2H))-one, C19H16F4O3
  42. Crystal structure of 2-amino-4-(2-fluoro-3-(trifluoromethyl)phenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[h]quinazolin-3-ium chloride, C20H18ClF4N3O
  43. Crystal structure of (2-phenylimino methylquinoline-κ 2 N,N′)-bis(1–phenylpyrazole-κ 2 C,N)-iridium(III) hexafluorophosphate, C34H26F6IrN6P
  44. Crystal structure of (3-hydroxy-4-methoxyphenyl)(pyrrolidin-1-yl)methanone, C12H15NO3
  45. The crystal structure of bis(trimethylsulfoxonium) catena-poly[µ2-hexabromido-indium(III)sodium(I)] C6H18O2S2NaInBr6
  46. Crystal structure of N-cyclopropyl-3-hydroxy-4-methoxybenzamide, C11H13NO3
  47. The crystal structure of (bis(benzimidazol-2-yl-methyl)amine-κ3N,N′,N″ )-(dihydrogen L-malate-κ2O,O ′)copper(II) perchlorate dihydrate, CuC20H24ClN5O12
  48. Crystal structure of (1E,1′E)-4,4′-(9,9-diethyl-9H-fluorene-2,7-diyl)dibenzaldehyde dioxime, C31H28N2O2
  49. Crystal structure of diethyl 1,9-bis(4-fluorophenyl)-4,6-diphenylhexahydro-3H-2,7,3,5-(epimethanetriyliminomethanetriyl)cyclopenta [b]pyridine-3,7(2H)-dicarboxylate, C40H36F2N2O4
  50. Crystal structure of bis(benzene-1 carboxylato-O 3,5-carboxyl-κ1O)-[(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) ─ benzene-1,3,5-tricarboxylic acid ─ water (1/2/4), C52H66N4NiO28
  51. Crystal structure of 1,4-dibromo-2,5-bis(2-methoxyethoxy)benzene-1,4-diol, C12H16Br2O4
  52. Crystal structure of dicarbonyl[N,N′-(1,2-dimethyl-1,2-ethanediylidene)bis[2,6-bis(1-methylethyl)benzenamine]-N,N′]nickel(0), C30H40N2NiO2
  53. Crystal structure of 1,4-dibromo-2,5-bis(prop-2-yn-1-yloxy)benzene, C12H8Br2O2
  54. Crystal structure of O-(3-(benzo[d]thiazol-2-yl)naphthalen-2-yl) O-phenyl carbonothioate, C24H15NO2S2
  55. The crystal structure of (E)-4-fluoro-N′-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H15FN2O2
  56. Crystal structure of (E)-1-(benzo[d]thiazol-2-yl)-N-(4,5-dihydropyren-2-yl)methanimine, C24H16N2S
  57. Crystal structure of 3-((4-bromophenyl)thio)-1H-indole, C14H10BrNS
  58. Synthesis and crystal structure of 1-((7-hydroxy-3-(4-hydroxy-3-nitrophenyl)-4-oxo-4H-chromen-8-yl)methyl)piperidin-1-ium-4-carboxylate monohydrate, C22H22N2O9
  59. Synthesis and crystal structure of (3E,5S,10S,13S,14S,17Z)-17-ethylidene-10,13-dimethylhexadecahydro-3H-cyclopenta[α]phenanthren-3-one O-(methacryloyl) oxime, C50H74N2O4
  60. Crystal structure of the hydrogen storage active phase La12Mg46LiMn
  61. The crystal structure of the salt: 4-((1,3-dioxoisoindolin-2-yl)carbamoyl)pyridine-1-ium 2-carboxybenzoate, C14H10N3O3·C8H5O4
  62. Crystal structure of (2-(2-pyridine)-benzimidazole-κ2 N,N′)-bis(1-phenylpyrazole-κ2 C,N)iridium(III) hexafluorophosphate, C30H22F6IrN7P
  63. Crystal structure of dichlorido-bis[2-(2,4-difluorophenyl)pyridine-κ1N]platinum(II), C22H14Cl2F4N2Pt
  64. Crystal structure of (5R,8R,9R,10R,12R,13R,14R, 17S,17Z)-2-((3-fluoropyridin-4-yl)methylene)-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, C36H52FNO3
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