(2E)-2-(4-ethoxybenzylidene)-3,4-dihydro-2H-naphthalen-1-one single crystal: Synthesis, growth, crystal structure, spectral characterization, biological evaluation and binding interactions with SARS-CoV-2 main protease.

A new α-Tetralone based chalcone compound, (2E)-2-(4-ethoxybenzylidene)-3,4-dihydro-2H-naphthalen-1-one (EBDN) has been synthesized by Claisen-Schmidt condensation reaction of α-Tetralone (1) with 4-Ethoxybenzaldehyde (2) in basic medium. Then it was allowed to grow through slow evaporation solution growth technique. The molecular structure of grown EBDN has been systematically characterized by SCXRD, FT-IR, 1H NMR and 13C NMR spectroscopic studies. The micro-hardness, thermal (TGA & DTA) and photoluminence studies of the synthesized EBDN were also examined. The EBDN was screened for its anti-inflammatory, antidiabetic and anti-oxidant activity. It has shown admirable anti-inflammatory and antidiabetic activity. Protein-Ligand interactions of EBDN with SARS-CoV-2 main protease (PDB code: 6yb7) also performed.

Crystal structure of (4-chloro-phen-yl)(4-methyl-piperidin-1-yl)methanone.

The title compound, C13H16ClNO, contains a methyl-piperidine ring in the stable chair conformation. The mean plane of the twisted piperidine ring subtends a dihedral angle of 39.89 (7)° with that of the benzene ring. In the crystal, weak C-H⋯O inter-actions link the mol-ecules along the a-axis direction to form infinite mol-ecular chains. H⋯H inter-atomic inter-actions, C-H⋯O inter-molecular inter-actions and weak dispersive forces stabilize mol-ecular packing and form a supra-molecular network, as established by Hirshfeld surface analysis.

Crystal structure of [4-(chloro-meth-yl)phen-yl](4-hy-droxy-piperidin-1-yl)methanone.

The title compound, C13H16ClNO2, crystallized with two independent mol-ecules in the asymmetric unit (A and B). The piperidinol ring in mol-ecule B is disordered over two positions with a site occupancy ratio of 0.667 (5):0.333 (5). In both mol-ecules these rings have a chair conformation, including the minor component in mol-ecule B. Their mean planes are inclined to the benzene ring by 45.57 (13)° in mol-ecule A, and by 50.5 (4)° for the major component of the piperidine ring in mol-ecule B. In the crystal, the individual mol-ecules are linked by O-H⋯O hydrogen bonds, forming chains of A and B mol-ecules along the [100] direction. The chains are inter-linked by C-H⋯O hydrogen bonds, forming ribbons.

Crystal structure of (4-hy-droxy-piperidin-1-yl)[4-(tri-fluoro-meth-yl)phen-yl]methanone.

The title compound, C13H14NO2F3, crystallises with two mol-ecules, A and B, in the asymmetric unit, with similar conformations. The dihedral angles between the piperidine and phenyl rings are 83.76 (2) and 75.23 (2)° in mol-ecules A and B, respectively. The bond-angle sums around the N atoms [359.1 and 359.7° for mol-ecules A and B, respectively] indicate sp (2) hybridization for these atoms. In the crystal, O-H⋯O hydrogen bonds link the mol-ecules into separate [100] chains of A and B mol-ecules. The chains are cross-linked by C-H⋯O inter-actions, generating alternating (001) sheets of A and B mol-ecules.

Crystal structure of (4-hy-droxy-piperidin-1-yl)(4-methyl-phen-yl)methanone.

In the title compound, C13H17NO2, the dihedral angle between the planes of the piperidine and benzene rings is 51.7 (2)°. The bond-angle sum around the N atom [359.8 (3)°] indicates sp (2) hybridization of the atom. In the crystal, O-H⋯O hydrogen bonds link the mol-ecules, forming chains along [001].

Crystal structure of the adduct (4-chloro-phen-yl)(4-hy-droxy-piperidin-1-yl)methanone-(4-chloro-phen-yl)(piperidin-1-yl)methanone (0.75/0.25).

In the title compound, 0.75C12H14ClNO2·0.25C12H14ClNO, which is an adduct comprising 0.75 4-hy-droxy-piperidin-1-yl or 0.25 4-piperidin-1-yl substituents on a common (4-chloro-phen-yl)methanone component; the dihedral angles between the benzene ring and the two piperidine rings are 51.6 (3) and 89.5 (7)°, respectively. The hy-droxy-piperidine ring is in a bis-ectional oriention (bi) with the phenyl ring. In the crystal, inter-molecular O-H⋯O hydrogen bonds between the hy-droxy-piperidine group and the keto O atom lead to the formation of chains extending along the c- axis direction.

Crystal structure of 2,2,4-trimethyl-2,3,4,5-tetra-hydro-1H-benzo[b][1,4]diazepine hemihydrate.

The title compound, C12H18N2·0.5H2O, crystallizes with two independent organic mol-ecules (A and B) in the asymmetric unit, together with a water mol-ecule of crystallization. The diazepine rings in each mol-ecule have a chair conformation. The dihedral angle between benzene ring and the mean plane of the diazepine ring is 21.15 (12)° in mol-ecule A and 17.42 (11)° in mol-ecule B. In the crystal, mol-ecules are linked by N-H⋯O and O-H⋯N hydrogen bonds, forming zigzag chains propagating along [001].

Crystal structure of (E)-1-(1-hy-droxy-naphthalen-2-yl)-3-(2,3,4-tri-meth-oxy-phen-yl)prop-2-en-1-one.

The title compound, C22H20O5, is composed of a hy-droxy-naphthyl ring and a tri-meth-oxy-phenyl ring [the planes of which are inclined to one another by 21.61 (10)°] bridged by an unsaturated prop-2-en-1-one group. The mean plane of the prop-2-en-1-one group [-C(=O)-C=C-] is inclined to that of the naphthyl system and benzene rings by 3.77 (14) and 18.01 (16)°, respectively. There is an intra-molecular O-H⋯O hydrogen bond present forming an S(6) ring motif. In the crystal, inversion-related mol-ecules are linked by a slipped-parallel π-π inter-action [inter-centroid distance = 3.8942 (13) Å, inter-planar distance = 3.478 (9) Šand slippage = 1.751 Å], and stack along the [101] direction. There are no other significant inter-molecular inter-actions present.

Crystal structure of bis-(prop-2-yn-1-yl) 5-nitro-isophthalate.

The whole mol-ecule of the title compound, C14H9NO6, is generated by twofold rotation symmetry; the twofold axis bis-ects the nitro group and the benzene ring. The nitro group is inclined to the benzene ring by 14.42 (9)°. The prop-2-yn-1-yl groups are inclined to the benzene ring by 13 (2)° and to each other by 24 (3)°; one directed above the plane of the benzene ring and the other below. In the crystal, mol-ecules are linked via pairs of C-H⋯O hydrogen bonds, forming inversion dimers with an R 2 (2)(18) ring motif. The dimers are linked by further C-H⋯O hydrogen bonds, forming sheets lying parallel to (100).

Crystal structure of 3-(4-meth-oxy-phen-yl)-2,3-di-hydro-1H-naphtho-[2,1-b]pyran-1-one.

In the title compound, C20H16O3, the hydro-pyran ring adopts a distorted half-chair conformation with the methine C atom and the ring O atom displaced by -0.554 (2) and 0.158 (1) Å, respectively, from the plane of the other four atoms (r.m.s. deviation = 0.020 Å). Its mean plane (all atoms) is inclined to the naphthalene ring system at a dihedral angle of 11.67 (1)°. The dihedral angle between the napthalene ring system and the phenyl ring is 71.84 (1)°. In the crystal, no diectional inter-actions beyond van der Waals contacts could be identified.

Crystal structure of 4-methyl-N-[2-(piperidin-1-yl)eth-yl]benzamide monohydrate.

In the title compound, C15H22N2O·H2O, the dihedral angle between the planes of the piperidine and benzene rings is 31.63 (1)°. The piperidine ring adopts a chair conformation. The water solvent mol-ecule is involved in inter-species O-H⋯O, O-H⋯N, N-H⋯O and weak C-H⋯O hydrogen-bonding inter-actions, giving rise to chains extending along [010].

Crystal structure of (E)-3-(3,4-di-meth-oxy-phen-yl)-1-(1-hy-droxy-naphthalen-2-yl)prop-2-en-1-one.

The mol-ecular structure of the title compound, C21H18O4, consists of a 3,4-di-meth-oxy-phenyl ring and a naphthalene ring system linked via a prop-2-en-1-one spacer. The mol-ecule is almost planar, with a dihedral angle between the benzene ring and the naphthalene ring system of 2.68 (12)°. There is an intra-molecular O-H⋯O hydrogen bond involving the adjacent hy-droxy and carbonyl groups. The mol-ecule has an E conformation about the C=C bond and the carbonyl group is syn with respect to the C=C bond. In the crystal, mol-ecules are linked by bifurcated C-H⋯(O,O) hydrogen bonds, enclosing an R 2 (1)(6) ring motif, and by a further C-H⋯O hydrogen bond, forming undulating sheets extending in b- and c-axis directions. There are π-π inter-actions between the sheets, involving inversion-related naphthalene and benzene rings [inter-centroid distance = 3.7452 (17) Å], forming a three-dimensional structure.

Crystal structure of 2-chloro-1-(3-ethyl-2,6-di-phenyl-piperidin-1-yl)ethanone.

In the racemic title compound, C21H24ClNO, the dihedral angle between the planes of the benzene rings is 86.52 (14)° and those between the benzene rings and the piperidine ring are 61.66 (14) and 86.39 (14)°. The piperidine ring adopts a twisted boat conformation. No directional inter-actions could be detected in the crystal.

Crystal structure of 4-chloro-N-[2-(piperidin-1-yl)eth-yl]benzamide monohydrate.

In the title compound, C14H19ClN2O2·H2O, the piperdine ring adopts a chair conformation. The dihedral angle between the mean plane of the piperidine ring and that of the phenyl ring is 41.64 (1)°. In the crystal, mol-ecules are linked by O-H⋯N, N-H⋯O and C-H⋯O hydrogen bonds involving the water mol-ecule, forming double-stranded chains propagating along [010].

Crystal structure of (2E)-3-(3-eth-oxy-4-hy-droxy-phen-yl)-1-(4-hy-droxy-phen-yl)prop-2-en-1-one.

In the title compound, C17H16O4, the dihedral angle between the benzene rings is 21.22 (1)° and the mean plane of the prop-2-en-1-one group makes dihedral angles of 10.60 (1) and 11.28 (1)°, respectively, with those of the hy-droxy-phenyl and eth-oxy-phenyl rings. The eth-oxy substituent forms a dihedral angle of 88.79 (2)° with the the prop-2-en-1-one group, which is found to be slightly twisted. In the crystal, phenolic O-H⋯O hydrogen bonds to the carbonyl O atom form a two-dimensional supra-molecular network structure lying parallel to (010).

Methyl 4'-(4-fluoro-phen-yl)-1'-methyl-3'-nitro-methyl-2-oxospiro-[indoline-3,2'-pyrrolidine]-3'-carboxyl-ate.

In the title compound, C(21)H(20)FN(3)O(5), the the pyrrolidine ring makes dihedral angles of 84.91 (6) and 62.38 (7)° with the oxindole unit and the fluoro-phenyl ring, respectively. The pyrrolidine ring assumes an envelope conformation with the spiro C atom as the flap. The crystal packing features weak N-H⋯N and C-H⋯O hydrogen bonds.

2-Chloro-1-(3,3-dimethyl-2,6-di-phenyl-piperidin-1-yl)ethanone.

In the title compound, C21H24ClNO, the piperidine ring adopts a chair conformation. The two phenyl rings are inclined to one another by 20.7 (1)°, and are inclined to the mean plane of the four planar atoms of the piperidine ring by 87.64 (10) and 70.8 (1)°. The mol-ecular structure features short intra-molecular C-H⋯Cl and C-H⋯O contacts. In the crystal, there are no significant inter-molecular inter-actions present.