Startseite Crystal structure of (E)-7-methoxy-2-(4-methoxy-2-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C20H17F3O3
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Crystal structure of (E)-7-methoxy-2-(4-methoxy-2-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C20H17F3O3

  • Shuai Lai ORCID logo , Yun Hou ORCID logo , Feng-Lan Zhao und Qing-Guo Meng EMAIL logo
Veröffentlicht/Copyright: 22. Februar 2023

Abstract

C20H17F3O3, monoclinic, P21/c (no. 14), a = 9.0684(4) Å, b = 13.1942(6) Å, c = 13.7883(7) Å, β = 96.250(5)°, V = 1639.97(13) Å3, Z = 4, R gt (F) = 0.0415, wR ref (F 2) = 0.1125, T = 100 K.

CCDC no.: 2080454

The crystal structure is shown in the figure. Displacement ellipsoids are drawn at the 40% probability level. 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: 0.15 × 0.13 × 0.12 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.12 mm−1
Diffractometer, scan mode: SuperNova,
θ max, completeness: 25.5°, >99%
N(hkl)measured, N(hkl)unique, R int: 7489, 3045, 0.033
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 2677
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 0.65903 (18) 0.85750 (12) 0.75806 (11) 0.0233 (4)
C2 0.52023 (17) 0.87935 (12) 0.80475 (11) 0.0227 (4)
C3 0.47743 (18) 0.98904 (12) 0.81346 (12) 0.0271 (4)
H3A 0.404935 0.994976 0.859948 0.033*
H3B 0.431623 1.012871 0.750752 0.033*
C4 0.61089 (19) 1.05553 (12) 0.84653 (12) 0.0273 (4)
H4A 0.581050 1.126148 0.842785 0.033*
H4B 0.645118 1.040365 0.914076 0.033*
C5 0.83547 (19) 1.11643 (12) 0.77025 (12) 0.0260 (4)
H5 0.822365 1.179616 0.797941 0.031*
C6 0.95318 (18) 1.10252 (12) 0.71576 (12) 0.0261 (4)
H6 1.018474 1.155375 0.707433 0.031*
C7 0.97262 (18) 1.00806 (12) 0.67346 (11) 0.0240 (4)
C8 0.87565 (18) 0.92996 (12) 0.68672 (11) 0.0234 (4)
H8 0.888982 0.867084 0.658471 0.028*
C9 0.75768 (17) 0.94476 (11) 0.74228 (11) 0.0215 (3)
C10 0.73627 (17) 1.03941 (12) 0.78504 (11) 0.0229 (4)
C11 0.45120 (18) 0.79930 (12) 0.83858 (11) 0.0233 (4)
H11 0.492558 0.736336 0.827811 0.028*
C12 0.31823 (17) 0.79841 (11) 0.89061 (11) 0.0220 (3)
C13 0.30686 (17) 0.73063 (11) 0.96888 (11) 0.0205 (3)
C14 0.18284 (17) 0.72872 (11) 1.01812 (11) 0.0223 (3)
H14 0.177658 0.683316 1.069226 0.027*
C15 0.06522 (17) 0.79426 (11) 0.99190 (11) 0.0227 (4)
C16 0.07080 (18) 0.85976 (12) 0.91389 (12) 0.0247 (4)
H16 −0.008410 0.902745 0.894950 0.030*
C17 0.19630 (18) 0.86046 (12) 0.86423 (12) 0.0250 (4)
H17 0.198868 0.904022 0.811408 0.030*
C18 1.16961 (19) 1.06935 (12) 0.58758 (13) 0.0315 (4)
H18A 1.102901 1.117475 0.554077 0.047*
H18B 1.237668 1.045225 0.544134 0.047*
H18C 1.223877 1.101359 0.642947 0.047*
C19 0.43031 (17) 0.65857 (12) 1.00020 (11) 0.0240 (4)
C20 −0.16949 (19) 0.85596 (13) 1.02981 (15) 0.0336 (4)
H20A −0.131895 0.923978 1.035071 0.050*
H20B −0.238349 0.845630 1.077069 0.050*
H20C −0.218968 0.845282 0.965470 0.050*
F1 0.56347 (10) 0.70360 (7) 1.01402 (7) 0.0332 (3)
F2 0.44254 (11) 0.58498 (7) 0.93359 (7) 0.0335 (3)
F3 0.41204 (11) 0.61127 (7) 1.08397 (7) 0.0306 (3)
O1 1.08689 (13) 0.98608 (8) 0.61966 (9) 0.0311 (3)
O2 0.69183 (14) 0.77092 (8) 0.73599 (9) 0.0321 (3)
O3 −0.04984 (12) 0.78627 (8) 1.04735 (8) 0.0268 (3)

Source of material

7-Methoxy-3,4-dihydronaphthalen-1(2H)-one (0.86 g, 4.90 mmol) and 4-methoxy-2-(trifluoromethyl)benzaldehyde (1.0 g, 4.90 mmol) were dissolved in 10 mL acetic acid. Then dry hydrogen chloride gas was flowed continuously into the solution for 45 min. After gas insertion, the reaction system was stirred at room temperature for 7 days. The response endpoint was detected by thin layer chromatography (TLC). When the reaction was stopped, the precipitate was filtered from the reaction system, then it was dissolved in distilled water and regulated to a neutral pH with saturated aqueous Na2CO3 solution. The precipitate was filtered from the system and dissolved with dichloromethane. The organic phase was washed successively with deionized water and brine, dried over anhydrous sodium sulfate and condensed under vacuum. The crude product was purified by silica-gel column chromatography (petroleum ether: ethyl acetate = 10:1, v:v). Single crystal was obtained under ambient conditions via solvent evaporation in the mixed solvents of dichloromethane and methanol (1:1, v:v) and drying under vacuo at 333 K for 3 h.

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), and d(C–H) = 0.97 Å (methylene), U iso(H) = 1.2U eq(C), and d(C–H) = 0.93 Å (aromatic), U iso(H) = 1.2U eq(C).

Comment

3,4-Dihydronaphthalen-1(2H)-ones (DHNs) derivatives with antitumor and anti-inflammatory activities have been investigated as novel modulators of allergic and inflammatory responses [4, 5]. Our interests lie in developing these derivatives as anti-neuroinflammatory drugs. In this study, we designed and synthesized a new DHNs derivative through Claisen–Schmidt condensation reaction and we obtained a new single crystal by introducing trifluoromethyl.

The title compound contains one drug molecule in the asymmetric unit (cf. the figure). Bond lengths and angles are all in the expected ranges [6]. The title molecule has an approximately linear structure. The parent nucleus is 3,4-dihydronaphthalen-1(2H)-one and the 7 position of the aromatic ring are methoxylated. The third and fourth positions of the parent nucleus are two methylene saturated carbons. The olefinic double bonds between 3,4-dihydronaphthalen-1(2H)-one and 4-methoxy-2-(trifluoromethyl)benzaldehyde groups and carbonyl group form a and b unsaturated ketones. With respect to the C(2) = C(11) olefinic bonds, 4-methoxy-2-(trifluoromethyl)benzaldehyde and carbonyl groups adopt the E stereochemistry [7], [8], [9]. Because of the distorting effect of 3,4-dihydronaphthalen-1(2H)-one, the 7-methoxyphenyl and 4-methoxy-2-(trifluoromethyl)benzaldehyde groups are not coplanar with each other, with a dihedral angle of approximately 60.6° [10]. This twisted configuration may increase the likelihood of interactions with bioactive molecules or the purposes of creating more potent biological activity [11, 12].


Corresponding author: Qing-Guo Meng, School of Pharmacy, Collaborative Innovation Center of Advanced Drug Delivery System and Biotech Drugs in Universities of Shandong, Key Laboratory of Molecular Pharmacology and Drug Evaluation (Yantai University), Ministry of Education, Yantai University, Yantai, P. R. China, E-mail:

Acknowledgements

This work was supported by Science and Technology Innovation Development Plan of Yantai (No. 2020XDRH105) and the National Natural Science Foundation of China (No. 81473104).

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

  2. Research funding: Science and Technology Innovation Development Plan of Yantai (No. 2020XDRH105) and the National Natural Science Foundation of China (No. 81473104).

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

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Received: 2023-01-11
Accepted: 2023-02-06
Published Online: 2023-02-22
Published in Print: 2023-06-27

© 2023 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 phenyl(3,3-dichloro-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one)methanone, C7H4Cl2N2O
  4. Crystal structure of poly[diaqua-bis(μ 2-1,4-diaminobutane-N:N′)cobalt(II)] dichloride, C8H28Cl2CoN4O2
  5. Synthesis and crystal structure of (4aR,7S)-7-hydroxy-7-isopropyl-1,1-dimethyldecahydro-2H,6H-8a,4a-(epoxymethano)phenanthren-12-one, C20H32O3
  6. The crystal structure of 1-(2-chlorobenzyl)-3-(3,5-dichlorophenyl)urea, C14H11Cl3N2O
  7. Crystal structure of tetrapropylammonium-1,3,5-thiadiazole-5-amido-2-carbamate – 1,2,4-thiadiazole-3,5-diamine – water (1/1/1), C17H37N9O3S2
  8. Tetrabutylammonium 1,3,5-thiadiazole-5-amido-2-carbamate—1,2,4-thiadiazole-3,5-diamine— water (1/1/1), C21H45N9O3S2
  9. The crystal structure of ((E)-2,4-dichloro-6-(((2-hydroxy-5-nitrophenyl)imino)methyl)phenolato-κ 3 N,O,O′)tris(pyridine-κN)manganese(II), C28H21Cl2MnN5O4
  10. The crystal structure of aqua-bis{2-bromo-6-((2-(2-phenylacetyl)hydrazineylidene)methyl)phenolato-κ3 N,O,O′}-dimethylformamide-κ1 O-erbium(III) chloride – dimethylformamide – water (1/2/1), C39H49N7O9Br2ClEr
  11. Crystal structure of (diaqua-bis(phenanthroline-K 2 N,N′)-tetrakis(m 2-3,4,5,6-tetrafluorophthalato-K 4 O,O:O′:O″;K 2 O:O′)dierbium (III) phenanthroline (1/2), C80H38Er2F16N8O18
  12. Crystal structure of (E)-7-methoxy-2-(4-methoxy-2-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C20H17F3O3
  13. The crystal structure of 4–(4,4,5,5–tetramethyl–1,3,2–dioxaborolan–2–yl)morpholine, C10H20BNO3
  14. The crystal structure of catena–poly[aqua(1-naphthoato-κ 2 O,O′)-(μ-1-naphthoato-κ 4 O:O,O′:O′)lead(II)], C22H16O5Pb
  15. The crystal structure of 1-(4-chlorophenyl)-3-cycloheptylurea, C14H19ClN2O
  16. The crystal structure of 4-(pyren-1-yl)butyl-4-nitrobenzoate, C27H21NO4
  17. Crystal structure of cyclo-(bis(µ2-3,3′-(1H-imidazole-3-ium-1,3-diyl)dipropionato-κ4 O,O′:O″,O″′)-dinitrato-κ2 O,O′-tetraoxido-diuranium(VI) C18H22N6O18U2
  18. The crystal structure of catena-[nitrato-κ 2 O,O′-(μ 3-3-iodobenzene-1,2-dicarboxylato-κ 4 O:O′:O″,O‴)-(2,2′:6′,2″-terpyridine-κ 3 N,N′,N″)lanthanum(III)], C23H14IN4O7La
  19. Redetermination of crystal structure of [bis(pyridin-2-ylmethyl)amine-κ 3 N,,]chloridopalladium(II) chloride monohydrate
  20. Crystal structure of catena-poly[triaqua-[bis(m2-4-(1H-1,2,4-triazol-1-yl)benzoato-k2O:O')-(4-(1H-1,2,4-triazol-1-yl)benzoato-k1O)-praseodymium (III) monohydrate], C27H26N9O10Pr
  21. Crystal structure of trans-diaqua-bis(methyl methylcarbamohydrazonothioato-κ2 N,N′) nickel(II) iodide semihydrate, C6H22N6O2NiS2I2·0.5H2O
  22. The crystal structure of 2-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)isoindolin-1-one, C17H13F4NOS
  23. The crystal structure of di-μ-1-naphthylacetato-κ 3 O,O′:O;κ 3 O:O,O′-bis[(1-naphthylacetato-κ 2 O,O′)(2,2′-bipyridine-κ 2 N,N′)lead(II)] monohydrate, C68H54N4O9Pb2
  24. Crystal structure of tetrapropylammonium guanidinium 4,4′-sulfonyldibenzoate monohydrate, C27H44N4O7S
  25. Crystal structure of bis(tetrapropylammonium) terephthalate – 1-(diaminomethylene)thiourea – water (1/2/4) C18H40N5O4S
  26. Crystal structure of (E)-7-fluoro-2-(4-morpholinobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C21H20FNO2
  27. The crystal structure of poly[diaqua-bis(μ 3-5-bromobenzene-1,3-dicarboxylato-κ 3 O,O,O′)-(μ 2-1,3-bis-(4-pyridyl)-propane-κ 2 N,N′)-dizinc(II))] – 5-bromobenzene-1,3-dicarboxylic acid [2/1], C37H29Br3N2O14Zn2
  28. The crystal structure of 2-bromo-1,3-phenylene bis(4-methylbenzenesulfonate), C20H17BrO6S2
  29. Crystal structure of europium dichromium icosaaluminum, EuCr2Al20
  30. The crystal structure of N1,N3-di((E)-benzylidene) isophthalohydrazide dihydrate, C 22 H 22 N 4 O 4
  31. Crystal structure of 7α,11α-dihydroxy-15-oxo-ent-kauran-16-en-19,6β-olide, C20H26O5
  32. Crystal structure of 4-chloro-N′-[(1E)-pyridin-3-ylmethylidene]benzohydrazide, C13H10ClN3O
  33. The crystal structure of (Z)-3-(1-(2-((E)-4-isopropylbenzylidene)hydrazinyl)ethylidene) chroman-2,4-dione, C21H20N2O3
  34. Crystal structure of E-7-fluoro-2-(2-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C18H12F4O
  35. Crystal structure of bis(6-aminopyridine-2-carboxylato–k2O,N)-bis(N,N-dimethylformamide-k1 O)zinc(II), C18H24N6O6Zn
  36. Crystal structure of 5-(adamantan-1-yl)-3-[(4-{[2-(trifluoromethyl)phenyl]-methyl}piperazin-1-yl)methyl]-1,3,4-oxadiazole-2(3H)-thione, C25H31F3N4OS
  37. Crystal structure of tetrapropylammonium bicarbonate–1-(diaminomethylene)thiourea – water (2/2/1), C30H72N10O7S2
  38. Crystal structure of tris(2,2′-bipyridine-κ2 N,N′)iron(II) triiodide – dichloromethane (2/1), C61H50Cl2Fe2I12N12
  39. Crystal structure of 2-amino-3-[2-(1,3,3-trimethyl-1,3-dihydro-indol-2-ylidene)-ethylideneamino]-but-2-enedinitrile, C17H17N5
  40. The crystal structure of 1-(2-chlorophenyl)-3-cycloheptylurea, C14H19ClN2O
  41. Crystal structure of potassium bis(pentaselenido-κ 2 Se 1,Se 5)palladate(II), K2[Pd(Se5)2]
  42. The crystal structure of 5,10-bis(2-methoxyethyl)-5,10-dihydro-[1,2,3,4]tetrathiocino[5,6-b:8, 7-b′]diindole, C22H22N2O2S4
  43. The crystal structure of 4-(4-iodophenyl)-5H-1,2,3-dithiazole-5-thione, C8H4INS3
  44. Crystal structure of bis{μ2-(4-acetyl-phenoxy)acetato-κ2 O:O′}-bis{μ2-(4-acetyl-phenoxy)acetato-κ3 O,O′:O)- bis{(4-acetyl-phenoxy)acetato-κ2 O,O′}-bis(phenanthrolin-κ2 N,N′)didysprosium(III) tetrahydrate, C84H78N4O28Dy2
  45. Crystal structure of Eu2Pd3.37(1)Zn13.63(1)
  46. Crystal structure of 2-methoxy-4-(methoxy-carbonyl)phenyl 2-chloro-4-fluorobenzoate, C16H12ClFO5
  47. Crystal structure of catena-poly[bis(μ2-dicyanamide-κ2 N:N′)-bis(4-vinylpyridine-κN)-copper(II)], C18H14CuN8
  48. The crystal structure of iguratimod-dimethylformamide (1/1), C17H14N2O6S·C3H7NO
  49. Synthesis and crystal structure of 1-((3R,10S,13S,17S)-10,13-dimethyl-3-(m-tolylamino)hexadecahydro-1H-cyclopenta[α]phenanthren-17-yl)ethan-1-one, C28H41NO
  50. The crystal structure of diaqua-bis(4-bromo-2-formylphenoxy)zinc(II), C14H12Br2O6Zn
  51. The crystal structure of tetra(1-ethylimidazole-κ 1 N)-[μ 4-imidazole-4,5-dicarboxylato-κ 4 O, N, O′, N′]-trioxido-divanadium, C25H33N10O7V2
  52. The crystal structure of (E)-N′-(1-(4-fluorophenyl)propylidene)-2-hydroxybenzohydrazide, C16H15FN2O2
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