Home Crystal structure of (E)-7-bromo-2-(3,5-dimethoxybenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C19H17BrO3
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Crystal structure of (E)-7-bromo-2-(3,5-dimethoxybenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C19H17BrO3

  • Yu-Long Zhang , Shu-Lian Liu , Gui-Ge Hou ORCID logo , Lei Wang ORCID logo and Xiao-Fan Zhang ORCID logo EMAIL logo
Published/Copyright: August 3, 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

C19H17BrO3, triclinic, P 1 ‾ (no. 2), a = 8.2887(7) Å, b = 8.4190(12) Å, c = 13.1164(15) Å, α = 93.634(11)°, β = 90.609(9)°, γ = 118.201(11)°, V = 804.17(18) Å3, Z = 2, R gt (F) = 0.0738, wR ref (F 2) = 0.1614, T = 150 K.

CCDC no.: 2161858

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: 0.15 × 0.12 × 0.10 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 2.57 mm−1
Diffractometer, scan mode: SuperNova
θ max, completeness: 25.5°, >99%
N(hkl)measured , N(hkl)unique, R int: 5429, 2985, 0.069
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 2546
N(param)refined: 211
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 1.06665 (8) 0.74238 (10) 0.21958 (5) 0.0303 (3)
C1 0.8426 (8) 0.5624 (8) 0.3815 (4) 0.0195 (13)
H1 0.771558 0.474543 0.330170 0.023*
C2 0.9975 (8) 0.7158 (8) 0.3582 (4) 0.0206 (13)
C3 1.1045 (8) 0.8522 (8) 0.4327 (5) 0.0231 (13)
H3 1.207276 0.955778 0.415461 0.028*
C4 1.0539 (8) 0.8295 (8) 0.5334 (5) 0.0217 (13)
H4 1.124545 0.919343 0.584029 0.026*
C5 0.8549 (8) 0.6535 (9) 0.6715 (5) 0.0244 (14)
H5A 0.887366 0.771045 0.705500 0.029*
H5B 0.928711 0.607489 0.703575 0.029*
C6 0.6522 (8) 0.5254 (8) 0.6865 (4) 0.0204 (13)
H6A 0.636370 0.496944 0.757402 0.024*
H6B 0.580705 0.585603 0.671510 0.024*
C7 0.5816 (7) 0.3522 (8) 0.6186 (4) 0.0172 (12)
C8 0.6324 (8) 0.3708 (8) 0.5091 (4) 0.0153 (12)
C9 0.7936 (8) 0.5406 (8) 0.4838 (4) 0.0169 (12)
C10 0.9000 (8) 0.6756 (8) 0.5605 (4) 0.0198 (13)
C11 0.4872 (7) 0.1826 (8) 0.6471 (4) 0.0164 (12)
H11 0.462205 0.091826 0.595573 0.020*
C12 0.4174 (7) 0.1188 (7) 0.7476 (4) 0.0158 (12)
C13 0.4095 (7) −0.0439 (8) 0.7722 (4) 0.0168 (12)
H13 0.445886 −0.107472 0.725625 0.020*
C14 0.3474 (7) −0.1101 (8) 0.8657 (4) 0.0171 (12)
C15 0.2896 (8) −0.0191 (8) 0.9355 (4) 0.0179 (12)
H15 0.249605 −0.063302 0.998698 0.021*
C16 0.2926 (8) 0.1385 (8) 0.9093 (4) 0.0187 (12)
C17 0.3555 (8) 0.2097 (8) 0.8166 (4) 0.0171 (12)
H17 0.356464 0.316094 0.800407 0.021*
C18 0.2627 (9) −0.3543 (9) 0.9729 (5) 0.0281 (15)
H18A 0.331427 −0.277078 1.031810 0.042*
H18B 0.262500 −0.468327 0.974168 0.042*
H18C 0.139025 −0.373505 0.973577 0.042*
C19 0.2004 (8) 0.1908 (8) 1.0759 (4) 0.0214 (13)
H19A 0.102114 0.069609 1.077040 0.032*
H19B 0.167062 0.273034 1.112066 0.032*
H19C 0.308928 0.199309 1.108233 0.032*
O1 0.5450 (6) 0.2496 (6) 0.4420 (3) 0.0240 (10)
O2 0.3450 (6) −0.2711 (6) 0.8822 (3) 0.0263 (10)
O3 0.2345 (6) 0.2361 (6) 0.9728 (3) 0.0252 (10)

Source of material

The preparation of the intermediate 7-bromo-3,4-dihydronaphthalen-1(2H)-one was similar to the previous reported method [4, 5], which was used to synthesize the aromatic tetralones in the next step. 7-Bromo-3,4-dihydronaphthalen-1(2H)-one (0.60 g, 2.7 mmol) and 3,5-dimethoxybenzaldehyde (0.67 g, 4.0 mmol) were dissolved in 5 mL of methanol. A NaOH solution (25%, 2 mL) was dropped to the above solution through a constant pressure dropping funnel. The mixture was stirred for 4 h at 298 K, and the progress of the reaction was traced by thin layer chromatography (TLC). After the completion of the reaction, the upper solution was poured off and the remaining solid was washed by the cold methanol and dried. The pure product of the title compound was separated by 200–300 mesh silica gel column (petroleum ether/ethyl acetate/methanol = 10:10:1, v/v/v).

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). The analysis of the F o/F c data and the two difference density peaks point to a twinning with an expected ratio smaller than 4:1. As the constituation of the target molecules is obtained without serious distorsions, a twin refinement was not undertaken.

Comment

Curcumin is a yellow phenolic pigment found mainly in the rhizome of turmeric, a plant of the ginger family. It was found to possess multiple anti-inflammatory, anti-tumour and anti-rheumatic effects without toxicity to humans at higher doses [6]. However, the poor bioavailability and unstable structure limited its clinical application [7]. In order to overcome the shortcoming of curcumin derivatives, a set of curcumin analogues were designed and synthesized in recent years. For example, halogenated bis(methoxybenzyl)-4-piperidone displays significant anti-cancer activity effects [8]. Boc-piperidone chalcones were novel cytotoxic drugs against highly metastatic cancer cells [9]. These results shows that curcumin derivatives have good bioactivity, which can be regarded as anti-inflammatory and anti-tumour agents [10, 11]. Based on the above studies, the target product of (E)-7-bromo-2-(3,5-dimethoxybenzylidene)-3,4-dihydronaphthalen-1(2H)-one was synthesized by the Claisen–Schmidt condensation reaction.

Single-crystal structure analysis reveals that there is one molecule in the asymmetric unit. In the molecule, the bond length of C7=C11 is 1.344(8) Å, other bond lengths and bond angles are similar to the values reported by related articles [12], [13], [14], [15]. As shown in the figure, the methoxybenzene ring and carbonyl group are arranged around the double bond with the torsion of C8–C7–C11–C12 being 180.0(5)°. Thus the title compound adopts the E stereochemistry. The C4 atom is deviated from the least-squares plane of the cyclohexanone ring with the value of 0.480(17) Å, which makes the cyclohexyl ring display an envelope conformation. The two benzene rings are not coplanar with the dihedral angle of 59.70(15)°. Through the further observation, it was found that adjacent molecules were linked to a chain structure along the b axis by the weak C18–H18B⃛O3 hydrogen bond. The chains were further interacted to form the bc plane by C18–H18A⃛Br1 interaction. The neighbouring chains further interact with each other via weak C3–H3⃛O1 hydrogen bond to form a 3D architecture.

Considering the bioactive property of aromatic-tetralones, –Br and –OMe substitutes were selected to modify the structure of curcumin analogue, which can act as the hydrogen-bonding acceptor and enhance interactions with proteins [16].

Corresponding author: Xiao-Fan Zhang, 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, Phone: +86 535 6913406, E-mail:

  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: 2022-08-03
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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  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-2022-0316
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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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