Home Crystal structure of (E)-7-bromo-2-(4-methoxybenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C18H15BrO2
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Crystal structure of (E)-7-bromo-2-(4-methoxybenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C18H15BrO2

  • Yu-Long Zhang , Shu-Lian Liu , Gui-Ge Hou ORCID logo , Xiao-Fan Zhang ORCID logo , Lei Wang ORCID logo and Wen-Yu Xin EMAIL logo
Published/Copyright: August 4, 2022
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 237 Issue 5

Abstract

C18H15BrO2, monoclinic, P21/n (no. 14), a = 9.1704(9) Å, b = 16.5309(13) Å, c = 10.3528(12) Å, β = 112.368(12)°, V = 1451.3(3) Å3, Z = 4, R gt (F) = 0.0405, wR ref (F 2) = 0.0677, T = 149.99(10) K.

CCDC no.: 2161857

The molecular 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: 0.14 × 0.12 × 0.10 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 2.834 mm−1
Diffractometer, scan mode: SuperNova
θ max, completeness: 25.5°, >99%
N(hkl) measured , N(hkl) unique, R int: 6642, 2694, 0.046
Criterion for I obs, N(hkl) gt: I obs > 2 σ(I obs), 1924
N(param) refined: 191
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
Br1 1.14469 (3) 0.10658 (2) 1.01994 (4) 0.02932 (13)
C1 0.8313 (3) 0.09750 (18) 0.8161 (4) 0.0187 (8)
H1 0.807693 0.073498 0.887069 0.022*
C2 0.9838 (3) 0.12313 (19) 0.8398 (4) 0.0200 (8)
C3 1.0195 (3) 0.15912 (19) 0.7355 (4) 0.0208 (8)
H3 1.122135 0.175817 0.753186 0.025*
C4 0.9027 (3) 0.17049 (18) 0.6043 (4) 0.0219 (9)
H4 0.927398 0.195144 0.534404 0.026*
C5 0.6201 (3) 0.1537 (2) 0.4332 (4) 0.0215 (8)
H5A 0.611318 0.103741 0.381547 0.026*
H5B 0.647639 0.196599 0.382756 0.026*
C6 0.4605 (3) 0.17306 (19) 0.4431 (4) 0.0201 (8)
H6A 0.465240 0.226296 0.483907 0.024*
H6B 0.378756 0.173909 0.350024 0.024*
C7 0.4194 (3) 0.11158 (18) 0.5304 (4) 0.0175 (8)
C8 0.5500 (3) 0.07868 (19) 0.6569 (4) 0.0190 (8)
C9 0.7139 (3) 0.10863 (18) 0.6828 (4) 0.0175 (8)
C10 0.7478 (3) 0.14516 (18) 0.5760 (4) 0.0185 (8)
C11 0.2729 (3) 0.08307 (19) 0.5047 (4) 0.0197 (8)
H11 0.266369 0.042066 0.563761 0.024*
C12 0.1223 (3) 0.10820 (18) 0.3957 (4) 0.0168 (8)
C13 0.0890 (3) 0.18799 (18) 0.3462 (4) 0.0189 (8)
H13 0.166563 0.227525 0.379100 0.023*
C14 −0.0590 (3) 0.20823 (19) 0.2486 (4) 0.0200 (8)
H14 −0.080132 0.261313 0.217325 0.024*
C15 −0.1757 (3) 0.1495 (2) 0.1974 (4) 0.0197 (8)
C16 −0.1452 (3) 0.07011 (19) 0.2444 (4) 0.0194 (8)
H16 −0.221899 0.030364 0.208992 0.023*
C17 0.0011 (3) 0.05112 (19) 0.3448 (4) 0.0201 (8)
H17 0.019526 −0.001388 0.379460 0.024*
C18 −0.4403 (3) 0.1179 (2) 0.0440 (4) 0.0307 (10)
H18A −0.406666 0.076397 −0.003329 0.046*
H18B −0.532917 0.143859 −0.020774 0.046*
H18C −0.464033 0.094194 0.118449 0.046*
O1 0.5271 (2) 0.03091 (14) 0.7381 (3) 0.0270 (6)
O2 −0.3167 (2) 0.17663 (13) 0.1006 (3) 0.0279 (6)

Source of material

7-Bromo-3,4-dihydronaphthalene-1(2H)-one (BDHA) was prepared according to the procedures delineated in existing literatures [4, 5]. In the next step, BDHA (0.50 g, 2.20 mmol) and 4-methoxybenzaldehyde (0.30 g, 2.20 mmol) were dissolved in 5 mL of methanol. 25% NaOH solution (2 mL) was added to the above solution and the mixture was stirred for 3.5 h at room temperature (monitored by TLC). The solution was poured to 20 mL water and extracted three times with 10 mL ethyl acetate. The organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure. The crude product was purified to obtain the title compound by silica gel column chromatography (Eluent: Petroleum ether/Ethyl acetate/Methanol = 10:10:1, v/v/v). The product was dissolved in methanol and light yellow crystals suitable for single crystal X-ray diffraction were obtained by slow evaporation.

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

1-Tetralones, a wide collection of aromatic bicyclic compounds containing a moiety of 3,4-dihydronaphthalen-1(2H)-one (DHN), are gaining more attention due to their chemical characteristics and potential application in pharmaceutical industry. Recent researches demonstrated that 1-tetralones had a broad spectrum of biological activity, and acted as anticancer drugs [6], antifungal agents [7], and protein inhibitors [8]. In order to obtain new drugs, it is necessary to modify the structure of existing biologically active matrices. A set of aryliden-1-tetralone derivatives have been designed and investigated [9], [10], [11], [12]. 6-Methoxy-2-phenyl-3,4-dihydronaphthalen-1(2H)-one was found to possess antineoplastic and antiviral properties [13]. As adenosine receptor antagonists, (E)-7-hydroxy-2-(4-hydroxybenzylidene)-3,4-dihydronaphthalen-1(2H)-one was proved to be an optimal drug candidate to treat neurodegenerative disorders [14]. As a part of our aim to design new anti-neuroinflammatory agents, aromatic-1-tetralones with chloro, fluoro, bromo, methyl and methoxy groups were synthesized by the Claisen–Schmidt condensation reaction, the crystals of (E)-7-bromo-2-(4-methoxybenzylidene)-3,4-dihydronaphthalen-1(2H)-one were obtained and its structure is reported here.

X-ray crystallographic analysis reveals that the title compound crystallizies in the monoclinic space group P 21/n with one molecule in the asymmetric unit (cf. the figure). The torsion angle of C8–C7–C11–C12 is 175.2(3)°, meaning that the title compound adopts the E stereochemistry. The length of C7=C8 olifinic bond is 1.351(4) Å, which is similar to those reported in tetralone-containing compounds [15], [16], [17], [18]. Because of the sp3 hybridization of C5 and C6 atoms, the cyclohexanone ring of 3,4-dihydronaphthalen-1(2H)-one displays a chair conformation. Simultaneously, the two benzene rings are turned to each other with a dihedral angle of 51.7(3)°. Though no classic hydrogen bonds were found in the crystal structure, adjacent molecules are connected to form one dimensional structure via the C18–H18A–O1 weak hydrogen bond, wich is further linked to form one layer in the ac plane by the C4–H···4pi interaction (pi represents the center of the methoxylbenzene ring, C4···pi = 3.548(4) Å). Because of the existence of dihydronaphthalenone and methoxy groups, the title compound may establish effectively hydrophobic interactions with some proteins. Additionally, the bromine atom will be able to enhance cell permeability and metabolic stability of the title compound. It is of great importance in the design and optimization of halogenated drugs.

Corresponding author: Wen-Yu Xin, School of Pharmacy, The Key Laboratory of Prescription Effect and Clinical Evaluation of State Administration of Traditional Chinese Medicine of China, Binzhou Medical University, Yantai, 264003, P. R. China, E-mail:

Funding source: Shandong Provincial Natural Science Foundation

Award Identifier / Grant number: ZR2019MB032

Funding source: College Youth Innovation Science and Technology Support Programme of Shandong Province

Award Identifier / Grant number: 2020KJK003

Funding source: Key R&D Programme of Shandong Province

Award Identifier / Grant number: 2019JZZY011104

Funding source: Shandong New Drug Loading & Release Technology and Preparation Engineering Laboratory

  1. Author contributions: 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. ZR2019MB032), College Youth Innovation Science and Technology Support Programme of Shandong Province (No. 2020KJK003), Key R&D Programme of Shandong Province (No. 2019JZZY011104), Shandong New Drug Loading & Release Technology and Preparation Engineering Laboratory.

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

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Received: 2022-06-18
Accepted: 2022-07-15
Published Online: 2022-08-04
Published in Print: 2022-10-26

© 2022 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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  52. Crystal structure of diaqua-diphenanthroline-κ2 N,N′-bis(μ2-2-carboxy-3,4,5,6-tetrafluorobenzoato-κ2 O:O′)-bis(μ2-tetrafluorophthalato-κ3 O,O′:O′)didysprosium(III) – phenanthroline (1/2), C80H38Dy2F16N8O18
  53. Crystal structure of bis(μ2-2-oxido-2-phenylacetato-κ3 O,O′:O′)-bis(N-oxido-benzamide-κ2 O,O′)-bis(propan-2-olato-κ1 O)dititanium(IV), C36H38N2O12Ti2
  54. Crystal structure of poly[diaqua-(μ2-1H-benzo[d][1,2,3]triazole-5-carboxylato-κ2 O:O′)(μ2-oxalato-κ4O,O:O″,O′″)europium(III)] monohydrate, C9H10N3O9Eu
  55. Crystal structure of bis((N-methyl-2-oxyethyl)amine)-bis(μ 2-N,N,N-tris(2-oxoethyl)amine)-bis(isopropoxy)-bis(μ 3-oxo)tetratitanium(IV)– isopropanol (1/2), C34H76N4O16Ti4
  56. Synthesis and crystal structure of ethyl 4-((4-iodobenzyl)amino)benzoate, C16H16INO2
  57. Crystal structure of (Z)-2-(tert-butyl)-5-((5-(tert- butyl)-2H-pyrrol-2-ylidene)(mesityl)methyl)-1H-pyrrole, C26H34N2
  58. Crystal structure of dimethylammonium poly[μ4-1,1′-(1,4- phenylenebis(methylene))bis(1H-pyrazole-3,5-dicarboxylato-κ6 N,O:O′:N′,O″:O‴) manganese(II)], C22H26MnN6O8
https://doi.org/10.1515/ncrs-2022-0315
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of 3-(1-(2-((5-methylthiophen-2-yl)methylene)hydrazinyl)ethylidene)chroman-2,4-dione, C17H14N2O3S
  4. Crystal structure of chlorido-(η 6-toluene)(5,5′-dimethyl-2,2′-bipyridine-κ2 N,N′)ruthenium(II) hexafluoridophosphate(V) ─ acetone (1/1) C22H26ClN2ORuPF6
  5. Crystal structure of 4-(((2-(3-(1-(3-(3-cyanophenyl)-6-oxopyridazin-1(6H)-yl)ethyl)phenyl) pyrimidin-5-yl)oxy)methyl)-1-methylpiperidin-1-ium chloride monohydrate, C30H33N6O2Cl
  6. The crystal structure of 2-chloro-N-((2-chlorophenyl)carbamoyl)nicotinamide, C13H9Cl2N3O2
  7. Crystal structure of 9-(t-butyl)-3,11-dihydro-6H-pyrazolo [1,5-a]pyrrolo[3′,2′:5,6]pyrido[4,3-d]pyrimidin-6-one hemihydrate, C30H32N10O3
  8. Crystal structure of di-μ2-hydroxido-tetrakis(6-methylpyridine-2-carboxylato-k2 N,O) diiron(III) trihydrate C28H32Fe2N4O13
  9. Crystal structure of catena-poly[qua-(μ2-2-aminoisophthalat-κ3 O,O′:O′′)(1,10-phenanthroline-κ2 N,N′)manganese(II)] C20H15MnN3O5
  10. Crystal structure of poly[(bis(isothiocyano)-bis(μ 2-(E)-N′-(pyridin-4-ylmethylene)isonicotinohydrazide))iron(II) – methanol – 1,4-dioxane (1/2/2), C36H44FeN10O8S2
  11. Crystal structure of (E)-N′-(1-(5-chloro-2-hydroxyphenyl)propylidene)-4-hydroxybenzohydrazide, C16H15ClN2O3
  12. Crystal structure of bis(μ2-benzoato-k2O:O′)-bis(μ2-benzoato-k3O,O′:O′)dinitrato-k2O,O′-bis(phenanthroline-k2 N,N′)dierbium(III), C52H36Er2N6O14
  13. Crystal structure of 4-ethyl-2-{[(4-nitrophenyl)methyl]sulfanyl}-6-oxo-1,6-dihydropyrimidine-5-carbonitrile, C14H12N4O3S
  14. Synthesis and crystal structure of 1-((3R,10S,13R,17S)-10,13-dimethyl-3- (phenylamino)hexadecahydro-1H-cyclopenta[α] phenanthren-17-yl)ethan-1-one, C27H39NO
  15. Crystal structre of 1,4-bis(bromomethyl)-2,3,5,6-tetramethylbenzene, C12H16Br2
  16. Crystal structure of 2-(adamantan-1-yl)-5-(3,5-dinitrophenyl)-1,3,4-oxadiazole, C18H18N4O5
  17. Crystal structure of (E)-N′-benzylidene-4-nitrobenzohydrazide – methanol (1/1), C15H15N3O4
  18. The crystal structure of 3-(2-bromophenyl)-1,5-di-p-tolylpentane-1,5-dione, C25H23BrO2
  19. Crystal structure of catena-poly[(μ 2-4,4′-bipyridine-κ2 N:N′)-bis(4-bromobenzoato-κ1 O)zinc(II)], C24H16Br2N2O4Zn
  20. Crystal structure of 1,1′-(1,2-ethanediyl)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2 S:S)zinc(II), C20H14N6ZnS4
  21. Crystal structure of pentacarbonyl-(μ2-propane-1,3-dithiolato-κ4 S:S,S′:S′)-(diphenyl(o-tolyl)phosphine-κ1 P)diiron (Fe-Fe), C27H23Fe2O5PS2
  22. The crystal structure of the cocrystal 4-hydroxy-3,5-dimethoxybenzoic acid–pyrazine-2-carboxamide(1/1), C14H15N3O6
  23. The crystal structure of dichlorido-bis((RS)-2-(4-chlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)hexanenitrile-κ1 N)zinc(II), C30H34Cl4N8Zn
  24. Crystal structure of the cocrystal 2,4,6-triamino-1,3,5-triazine – 1H-isoindole-1,3(2H)-dione – methanol (1/1/1), C12H15N7O3
  25. The crystal structure of methyl 4-((3,5-di-tert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)methyl) benzoate, C23H28O3
  26. Crystal structure of (poly[µ2-(1H-pyrazol-1-yl)methyl]-1H-benzotriazole-κ 2 N:N)-(nitrato-κ 2 O:O′) silver(I), C9H8AgN7O3
  27. Crystal structure of tetraaqua-bis[4-(1H-1,2,4-triazol-1-yl)benzoato-k1 N]cadmium(II), C18H20CdN6O8
  28. The crystal structure of diaqua-bis(pyrazolo[1,5-a]pyrimidine-3-carboxylato-κ2N,O)nickel(II) dihydrate, C14H16N6O8Ni
  29. Crystal structure of poly[μ2-aqua-aqua-(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2 N:N′)-(μ2-4,4′-(1H-1,2,4-triazole-3,5-diyl)dibenzoato-κ2 O:O′)-(μ4-4,4′-(1H-1,2,4-triazole-3,5-diyl)dibenzoato-κ5 O,O′:O″:O′″:O′″)dicobalt(II)] – water – dimethylformamide (1/1/1) C44H43N11O12Co2
  30. Crystal structure of N-((Z)-amino(((E)-amino(phenylamino)methylene) amino)methylene)benzenaminium chloride – benzo[f]isoquinolino[3,4-b][1,8]naphthyridine – tetrahydrofurane (1/2/2), C60H54ClN11O2
  31. The crystal structure of Chrysosplenol D, C18H16O8
  32. Crystal structure of poly[deca aqua-bis(μ 4-2-(triazol-1-yl)-benzene-1,3,5-tricarboxylato)- bis(μ 5-2-(triazol-1-yl)-benzene-1,3-dicarboxylato-5-carboxyl acid) pentamanganese(II)] dihydrate, C44H42Mn5N12O36
  33. Synthesis and crystal structure of (E)-1-(4-(((E)-3-(tert-butyl)-2-hydroxybenzylidene)amino)phenyl)ethan-1-one O-methyl oxime, C20H24N2O2
  34. The crystal structure of 4,4′-dichloro-6,6′-dimethoxy-2,2′,3,3′,5,5′- hexanitroazobenzene, C14H6N8O14Cl2
  35. Crystal structure of N 2,N 4-dimesitylpentane-2,4-diamine, C23H34N2
  36. Crystal structure of (1,4,7,10,13,16-hexaoxacyclooctadecane-κ 6O6)potassium(2-methylphenylamino)ethyl-2-methylphenylamide ammoniate (1/3.5), [K(18-crown-6)](o-CH3C6H4)NH(CH2)2N(o-CH3C6H4) 3.5 NH3, C28H53.5KN5.5O6
  37. The crystal structure of N′,N″,2-tris((E)-5-chloro-2-hydroxybenzylidene)hydrazine-1-carbohydrazonhydrazide hydrochloride – methanol (1/3), C25H30Cl4N6O6
  38. Crystal structure of (E)-7-bromo-2-(3,5-dimethoxybenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C19H17BrO3
  39. Crystal structure of (E)-N′-(1-(5-chloro-2-hydroxyphenyl) ethylidene)-4-hydroxybenzohydrazide, C15H13ClN2O3
  40. {2-(((2-aminoethyl)imino)methyl)-6-bromophenolato-κ3 N,N′,O}iron(III) nitrate, C18H20Br2FeN5O5
  41. Crystal structure of 2-(tert-pentyl)anthracene-9,10-dione, C19H18O2
  42. Crystal structure of 5,5′-(1,4-phenylene)bis(1H-imidazol-3-ium) bis(2-(2-(carboxymethyl)phenyl)acetate), C32H30N4O8
  43. Crystal structure of N 2,N 6-bis(2-(((E)-naphthalen-1-ylmethylene)amino)phenyl)pyridine-2,6-dicarboxamide, C41H29N5O2
  44. The crystal structure of 3-amino-1,2,4-triazolium 2,4,5-trinitroimidazolate, C5H5O6N9
  45. Hydrogen bonded dimers in the crystal structure of 2-chloro-N-(phenylcarbamoyl)nicotinamide, C26H20Cl2N6O4
  46. The crystal structure of 4,4′-bipyridine-5,6,7-trihydroxy-2-phenyl-4H-chromen-4-one-water(1/2/2), C40H32N2O12
  47. Crystal structure of N,N'-bis(4-fluoro-salicylaldehyde)-3,6-dioxa-1,8-diaminooctane, C20H22F2N2O4
  48. Crystal structure of 3-(1,3-dinitropropan-2-yl)-4H-chromen-4-one, C12H10N2O6
  49. The crystal structure of (4-(2-bromoethoxy)-phenyl)(phenyl)methanone, C15H13BrO2
  50. Crystal structure of (E)-7-bromo-2-(4-methoxybenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C18H15BrO2
  51. Crystal structure of dichlorido-tetrakis((E)-(RS)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol-κ 1 N)cadmium(II), C60H68O4N12Cl10Cd
  52. Crystal structure of diaqua-diphenanthroline-κ2 N,N′-bis(μ2-2-carboxy-3,4,5,6-tetrafluorobenzoato-κ2 O:O′)-bis(μ2-tetrafluorophthalato-κ3 O,O′:O′)didysprosium(III) – phenanthroline (1/2), C80H38Dy2F16N8O18
  53. Crystal structure of bis(μ2-2-oxido-2-phenylacetato-κ3 O,O′:O′)-bis(N-oxido-benzamide-κ2 O,O′)-bis(propan-2-olato-κ1 O)dititanium(IV), C36H38N2O12Ti2
  54. Crystal structure of poly[diaqua-(μ2-1H-benzo[d][1,2,3]triazole-5-carboxylato-κ2 O:O′)(μ2-oxalato-κ4O,O:O″,O′″)europium(III)] monohydrate, C9H10N3O9Eu
  55. Crystal structure of bis((N-methyl-2-oxyethyl)amine)-bis(μ 2-N,N,N-tris(2-oxoethyl)amine)-bis(isopropoxy)-bis(μ 3-oxo)tetratitanium(IV)– isopropanol (1/2), C34H76N4O16Ti4
  56. Synthesis and crystal structure of ethyl 4-((4-iodobenzyl)amino)benzoate, C16H16INO2
  57. Crystal structure of (Z)-2-(tert-butyl)-5-((5-(tert- butyl)-2H-pyrrol-2-ylidene)(mesityl)methyl)-1H-pyrrole, C26H34N2
  58. Crystal structure of dimethylammonium poly[μ4-1,1′-(1,4- phenylenebis(methylene))bis(1H-pyrazole-3,5-dicarboxylato-κ6 N,O:O′:N′,O″:O‴) manganese(II)], C22H26MnN6O8
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