Home Crystal structure of 2-((2-fluoro-4-(trifluoromethyl)phenyl)(hydroxy)methyl)-7-methoxy-3,4-dihydronaphthalen-1((2H))-one, C19H16F4O3
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Crystal structure of 2-((2-fluoro-4-(trifluoromethyl)phenyl)(hydroxy)methyl)-7-methoxy-3,4-dihydronaphthalen-1((2H))-one, C19H16F4O3

  • Yu-Lun Li , Qing-Guo Meng , Gui-Ge Hou ORCID logo and Zi-Kai Geng EMAIL logo
Published/Copyright: October 10, 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

C19H16F4O3, monoclinic, P21/n (no. 14), a = 9.5792(5) Å, b = 9.5542(4) Å, c = 17.6986(9) Å, β = 99.508(5)∘, V = 1597.55(14) Å3, Z = 4, R gt (F) = 0.0481, wR ref (F 2) = 0.1153, T = 293 K.

CCDC no.: 2272259

The crystal structure is shown in the Figure. Displacement ellipsoids are drawn at the 40 % probability level.

Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Colourless block
Size: 0.12 × 0.12 × 0.10 mm
Wavelength:

μ: 		Mo Kα radiation (0.71073 Å)

0.13 mm−1
Diffractometer, scan mode:

θ max, completeness:		 SuperNova,

25.5°, >99 %
N(hkl)measured , N(hkl)unique, R int: 7486, 2984, 0.028
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 2502
N(param)refined: 237
Programs: CrysAlisPRO [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 0.5783 (2) 0.2291 (2) 0.90120 (11) 0.0129 (4)
C2 0.4323 (2) 0.2717 (2) 0.91677 (11) 0.0126 (4)
H2 0.443743 0.361583 0.943790 0.015*
C3 0.3316 (2) 0.2974 (2) 0.84093 (12) 0.0152 (5)
H3A 0.323081 0.212900 0.810155 0.018*
H3B 0.238366 0.322276 0.851173 0.018*
C4 0.3905 (2) 0.4162 (2) 0.79752 (12) 0.0160 (5)
H4A 0.330365 0.428978 0.748260 0.019*
H4B 0.389467 0.502565 0.826261 0.019*
C5 0.5940 (2) 0.4459 (2) 0.72495 (12) 0.0175 (5)
H5 0.536793 0.505706 0.691771 0.021*
C6 0.7316 (2) 0.4195 (2) 0.71239 (12) 0.0171 (5)
H6 0.765118 0.460905 0.671324 0.021*
C7 0.8182 (2) 0.3306 (2) 0.76195 (12) 0.0146 (4)
C8 0.7667 (2) 0.2699 (2) 0.82302 (11) 0.0137 (4)
H8 0.824690 0.211162 0.856419 0.016*
C9 0.6285 (2) 0.2962 (2) 0.83480 (11) 0.0121 (4)
C10 0.5396 (2) 0.3859 (2) 0.78526 (11) 0.0131 (4)
C11 0.3767 (2) 0.1676 (2) 0.97036 (11) 0.0139 (4)
H11 0.451738 0.150908 1.014224 0.017*
C12 0.2467 (2) 0.2205 (2) 1.00053 (11) 0.0126 (4)
C13 0.2563 (2) 0.3275 (2) 1.05421 (12) 0.0155 (4)
C14 0.1444 (2) 0.3740 (2) 1.08781 (12) 0.0178 (5)
H14 0.156028 0.445362 1.124055 0.021*
C15 0.0140 (2) 0.3102 (2) 1.06534 (12) 0.0160 (5)
C16 −0.0024 (2) 0.2048 (2) 1.01059 (12) 0.0168 (5)
H16 −0.090617 0.163869 0.995184 0.020*
C17 0.1134 (2) 0.1609 (2) 0.97897 (12) 0.0159 (5)
H17 0.101724 0.089981 0.942492 0.019*
C18 −0.1117 (2) 0.3531 (2) 1.09992 (13) 0.0217 (5)
C19 1.0140 (2) 0.3652 (3) 0.69570 (12) 0.0216 (5)
H19A 0.955676 0.347368 0.647115 0.032*
H19B 1.107654 0.330063 0.695010 0.032*
H19C 1.018278 0.464145 0.705200 0.032*
F1 0.38489 (13) 0.38979 (13) 1.07585 (7) 0.0224 (3)
F2 −0.21041 (16) 0.41932 (17) 1.05058 (9) 0.0416 (4)
F3 −0.07929 (17) 0.4326 (2) 1.16122 (10) 0.0587 (6)
F4 −0.18188 (16) 0.24189 (16) 1.12227 (9) 0.0406 (4)
O1 0.65304 (15) 0.14541 (15) 0.94221 (8) 0.0171 (3)
O2 0.95477 (16) 0.29652 (16) 0.75505 (8) 0.0194 (4)
O3 0.34839 (16) 0.03904 (15) 0.92984 (8) 0.0167 (3)
H3 0.345647 −0.024889 0.960473 0.025*

1 Source of material

The raw material 7-methoxy-3,4-dihydronaphthalene-1(2H)-one was obtained according to a literature [4]. The raw material (0.53 g, 3.0 mmol) and 2-fluoro-4-(trifluoromethyl)benzaldehyde (0.58 g, 3.0 mmol) were dissolved in 15 mL of methanol. About 5.0 mL of 20 % NaOH solution was added dropwise. The mixture was stirred at room temperature for about 1 h, and detected the reaction process by Thin-Layer Chromatography (TLC). The solvent was then removed by pouring, and the residues were purified on a silica gel by column chromatography using petroleum ether/EtOAc (2:1, v/v) as the eluent to obtain the light yellow solid of the title compound in 82.2 % yield.

2 Experimental details

The H atoms were placed in idealized positions and treated as riding on their parent atoms, with d(C–H) = 0.96 Å(methyl), U iso(H) = 1.5U eq(C); d(C–H) = 0.97 Å(methylene), U iso(H) = 1.2U eq(C); U iso(H) = 1.2U eq(C); d(C–H) = 0.93 Å(aromatic), U iso(H) = 1.2U eq(C); and d(O–H) = 0.82 Å(hydroxyl), U iso(H) = 1.5U eq(O), respectively.

3 Comment

3,4-Dihydronaphthalen-1(2H)-one is an active fragment with potential for the treatment of allergies and inflammatory phenomena among others [5]. In our previous study, we demonstrated that compounds with 3,4-dihydronaphthalen-1(2H)-one fragment could have inhibitory effects on the NF-κB signaling pathway [6], so we introduced electron-withdrawing groups fluorine atoms and trifluoromethyl side chains based on the original compounds with aromatic aldehydes through the Claisen–Schmidt reaction because their lipophilicity could enhance the membrane permeability of the drug, the stabilized C–F bond could improve the metabolic stability and prolong the duration of in vivo action. It is well known that fluorine atoms are the strongly electronegative that can form hydrogen bonds with the target proteins, thus enhancing the inhibitory effect of the drug against NF-κB [7]. Previously, we reported a series of condensation products with electron-donoring and electron-withdrawing groups, which were obtained by Claisen–Schmidt condensation reaction between aromatic aldehydes and 3,4-dihydronaphthalen-1(2H)-one [8], [9], [10], [11]. The common structural features is the formation of α,β-unsaturated ketones. In this study, we still expected the compound containing the α,β-unsaturated ketone, but our structural analysis of the title compound revealed that there is β-hydroxyketone unit [12] but not β-unsaturated ketone unit.

Single-crystal structure analysis reveals that there is only a title molecule in the asymmetric unit (cf. the Figure). The bond lengths and bond angles of the title compound are within the normal range and are in agreement with previous reports [7, 9, 11, 13]. The parent nucleus of this compound is 3,4-dihydronaphthalen-1(2H)-one with a methoxy group attached to C(7), while a 2-fluoro-4-(trifluoromethyl)phenyl substituted β-hydroxyketone attached to C(2). Interestingly, C(11) is a chiral carbon atom. In the solid state, the molecules crystallize in a centrosymmetric space group, P21/n, and the whole does not show chiral properties. In addition, the benzene ring is substituted with electron-withdrawing substituents (–F and –CF3), and the substituted benzene ring is not coplanar with the parent nucleus with a big dihedral angle of about 85.20(2)∘. The C(11)-substituted hydroxyl group and C(1)=O(1) group did not form the intramolecular hydrogen bond, and the torsion angle of C(1)–C(2)–C(1)–O(3) is about −68.3(2)∘, and the torsion angle of O(1)=C(1)–C(2)–C(11) is about −17.7(3)∘, respectively. The C(11)-substituted hydroxyl group and the C(13)-substituted fluorine atom are in the trans structure, so that the torsion angle of O(3)–C(11)–C(12)–C(13) is about 166.92(17)∘, and the torsion angle of C(11)–C(12)–C(13)–F(1) is about 3.8(3)∘, respectively.

Corresponding author: Zi-Kai Geng, School of Pharmacy, Binzhou Medical University, Yantai, 264003, P.R. China, E-mail:

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

  2. Research funding: Shandong Provincial Natural Science Foundation (No. ZR2023MH190).

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

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Received: 2023-08-16
Accepted: 2023-09-27
Published Online: 2023-10-10
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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  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
https://doi.org/10.1515/ncrs-2023-0373
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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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