Startseite Crystal structure of (E)-7-fluoro-2-(4-morpholinobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C21H20FNO2
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Crystal structure of (E)-7-fluoro-2-(4-morpholinobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C21H20FNO2

  • Han-Lin Luo , Wen-Xuan Li , Xian-Yong Bai , Qing-Guo Meng und Yun Hou ORCID logo EMAIL logo
Veröffentlicht/Copyright: 14. März 2023

Abstract

C 21 H 20 F N O 2 , triclinic, P1̄ (no. 2), a = 9.2201(7) Å, b = 9.3195(8) Å, c = 11.4012(9) Å, α =  103.880 ( 7 ) ° , β =  100.987 ( 7 ) ° , γ =  115.090 ( 7 ) ° , V = 1796.31(20)  Å 3 , Z = 2, R g t (F) = 0.0421, w R r e f ( F 2 ) = 0.1136, T = 293 K.

CCDC no.: 2213130

The crystal structure is shown in the Figure. Displacement ellipsoids are drawn at the 30% 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: Mo radiation (0.71073 Å)
μ: 0.10 mm−1
Diffractometer, scan mode: SuperNova
θ max, completeness: 25.5°, >99%
N(hkl)measured , N(hkl)unique, R int: 5331, 3015, 0.025
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 2363
N(param)refined: 227
Programs: CrysAlis PRO [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 0.56397 (17) 1.19487 (19) 0.63909 (14) 0.0264 (3)
C2 0.40275 (17) 1.08726 (18) 0.65534 (14) 0.0268 (3)
C3 0.24048 (17) 1.01839 (19) 0.54719 (15) 0.0295 (4)
H3A 0.145851 0.984535 0.579472 0.035*
H3B 0.222835 0.918155 0.482222 0.035*
C4 0.24340 (17) 1.14812 (19) 0.48648 (15) 0.0310 (4)
H4A 0.146647 1.091689 0.408305 0.037*
H4B 0.231542 1.234177 0.544562 0.037*
C5 0.40381 (18) 1.2947 (2) 0.35557 (15) 0.0335 (4)
H5 0.301791 1.274575 0.302513 0.040*
C6 0.55297 (19) 1.3851 (2) 0.33312 (15) 0.0359 (4)
H6 0.552333 1.425014 0.265812 0.043*
C7 0.70260 (17) 1.41380 (19) 0.41397 (15) 0.0301 (4)
C8 0.70804 (17) 1.35272 (18) 0.51109 (14) 0.0278 (4)
H8 0.810702 1.372226 0.562599 0.033*
C9 0.55638 (16) 1.26018 (17) 0.53188 (14) 0.0246 (3)
C10 0.40287 (17) 1.23331 (18) 0.45558 (14) 0.0272 (3)
C11 0.41659 (18) 1.06564 (19) 0.76909 (15) 0.0290 (4)
H11 0.527895 1.120775 0.824305 0.035*
C12 0.29142 (18) 0.97297 (19) 0.82209 (14) 0.0284 (3)
C13 0.33310 (18) 1.03022 (19) 0.95568 (14) 0.0312 (4)
H13 0.438261 1.124989 1.005246 0.037*
C14 0.22585 (17) 0.95279 (19) 1.01631 (14) 0.0310 (4)
H14 0.257798 0.998772 1.105025 0.037*
C15 0.06777 (17) 0.80456 (18) 0.94679 (14) 0.0265 (3)
C16 0.02699 (18) 0.74408 (18) 0.81312 (14) 0.0295 (4)
H16 −0.075580 0.645934 0.763587 0.035*
C17 0.13453 (17) 0.82593 (19) 0.75324 (14) 0.0299 (4)
H17 0.101848 0.782103 0.664372 0.036*
C18 −0.01093 (18) 0.81091 (19) 1.14081 (14) 0.0315 (4)
H18A −0.050767 0.892291 1.143258 0.038*
H18B 0.109467 0.873045 1.189358 0.038*
C19 −0.10442 (19) 0.6894 (2) 1.20107 (16) 0.0427 (4)
H19A −0.055334 0.616601 1.207199 0.051*
H19B −0.089887 0.753469 1.287273 0.051*
C20 −0.2997 (2) 0.4894 (2) 1.00609 (17) 0.0417 (4)
H20A −0.419576 0.415885 0.957357 0.050*
H20B −0.249243 0.417988 1.013519 0.050*
C21 −0.21681 (18) 0.6007 (2) 0.93542 (16) 0.0386 (4)
H21A −0.227185 0.529976 0.853037 0.046*
H21B −0.275024 0.663445 0.920018 0.046*
F1 0.85045 (10) 1.50772 (11) 0.39625 (10) 0.0426 (3)
N1 −0.03751 (14) 0.71990 (15) 1.00812 (11) 0.0294 (3)
O1 0.70278 (12) 1.23344 (15) 0.71052 (11) 0.0407 (3)
O2 −0.28086 (13) 0.58668 (15) 1.13005 (11) 0.0442 (3)

1 Source of material

The intermediate 7-fluoro-3,4-dihydronaphthalen-1(2H)-one was synthesized in accordance with the literature synthesis approach [4]. In a 50 mL spherical backside flask, 7-fluoro-3,4-dihydronaphthalen-1(2H)-one (1.00 g, 6.09 mmol) and 4-morpholinobenzaldehyde (1.16 g, 6.09 mmol) were dissolved in 10 mL of methanol under an ice-cold salt tub at 268 K. Add 5 mL of 25% NaOH aqueous solution dropwise, and the gadget turns into turbid after 5 min with a white precipitate. The response used to be monitored through thin-layer chromatography (TLC, Dichloromethane:Methanol = 40:1), v/v. At the stop of the reaction, the mixture were once filtered, and the filter residue used to be washed in three instances with 50% aqueous methanol. The title compound, 7-fluoro-2-(4-morpholinobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, was purified with the aid of silica gel column chromatography (Dichloromethane:Methanol = 20:1), v/v to acquire colourless crystals.

2 Experimental details

The H atoms were placed in idealized positions and treated as riding on their parent atoms, with d (C–H) = 0.97 Å (methylene), U i s o (H) = 1.2 U e q (C), and d (C–H) = 0.93 Å (aromatic), U i s o (H) = 1.2 U e q (C).

3 Comment

Recently, 3,4-dihydronaphthalen-1(2H)-one derivatives (DHNs) were reported to improve their toxicity and anti-neuroinflammatory effects [5]. The substituents of some DHNs include halogens, methoxies, substituted phenyl groups, aromatic heterocycles and so on. Therein, methoxy-substituted DHN derivative showed lower toxicity and more potential anti-neuroinflammatory effects through inhibiting the activation of NF-κB signaling pathway [6]. For further structural optimization, a morpholine ring was added to the aromatic ring of DHNs in this experiment, and the title compound was synthesized by the Claisen–Schmidt condensation reaction between 7-fluoro-3,4-dihydronaphthalen-1(2H)-one and 4-morpholinobenzaldehyde.

Single-crystal structure analysis reveals that there is one DHN molecule in the asymmetric unit (cf. the Figure). Bond lengths and angles are all in the expected ranges. The 7 position of 3,4-dihydronaphthalen-1(2H)-one is substituted by electron-withdrawing fluorine substituent. The fluorine atom can act as a hydrogen bonding acceptor [7]. Through the Claisen–Schmidt condensation reaction between 3,4-dihydronaphthalen-1(2H)-one and aromatic aldehydes, the title compound formed α, β– unsaturated ketone structural characteristic. It adopts the E stereochemistry of the olefinic double bond [8, 9]. The bond length of C(2) = C(11) bonds is 1.350(2) Å, which is consistent with the range of bond lengths of olefinic bonds. The torsion angle of C(1)–C(2)–C(11)–C(12) is 179.24 ( 14 ) ° , while the torsion angle of C(3)–C(2)–C(11)–C(12) is 1.6 ( 3 ) ° . In addition, two methylene groups affect the molecular coplanarity resulting in a certain amount of distortion between the 4-morpholinophenyl ring and 3,4-dihydronaphthalen-1(2H)-one. Their dihedral angle is about 45.72 ( 2 ) ° . At the end of the title compound, there is 4-morpholino substituent, which exhibits “chair” conformation [10]. The distance of N(1)–O(2) is 2.857(3) Å. The torsion angle of O(2)–C(19)–C(18)–N(1) is 55.64 ( 17 ) ° , while the torsion angle of O(2)–C(20)–C(21)–N(1) is 56.09 ( 17 ) ° . In general, the entire molecule forms a linear structure [11, 12].


Corresponding author: Yun Hou, School of Basic Medical Sciences, Binzhou Medical University, Yantai, 264003, P. R. China, E-mail:

Funding source: Science and Technology Innovation Development Plan of Yantai

Award Identifier / Grant number: 2022XDRH003

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

  2. Research funding: This work was supported by Science and Technology Innovation Development Plan of Yantai (No. 2022XDRH003) and Key support projects (inheritance and development of traditional Chinese Medicine) of the State Administration of traditional Chinese medicine.

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

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Received: 2023-02-06
Accepted: 2023-02-26
Published Online: 2023-03-14
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
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  19. Redetermination of crystal structure of [bis(pyridin-2-ylmethyl)amine-κ 3 N,,]chloridopalladium(II) chloride monohydrate
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  22. The crystal structure of 2-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)isoindolin-1-one, C17H13F4NOS
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  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
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  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]
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  50. The crystal structure of diaqua-bis(4-bromo-2-formylphenoxy)zinc(II), C14H12Br2O6Zn
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