Molecular structure, FT-IR, first order hyperpolarizability, NBO analysis, HOMO and LUMO analysis of 2-(4-chlorophenyl)-2-oxoethyl 3-methylbenzoate by HF and density functional methods.

2-(4-Chlorophenyl)-2-oxoethyl 3-methylbenzoate is synthesized by reacting 4-chlorophenacyl bromide with 2-methylbenzoic acid using a slight excess of potassium or sodium carbonate in DMF medium at room temperature. The structure of the compound was confirmed by IR and single-crystal X-ray diffraction studies. FT-IR spectrum of 2-(4-chlorophenyl)-2-oxoethyl-3-nitrobenzoate was recorded and analyzed. The crystal structure is also described. The vibrational wavenumbers were computed using HF and DFT methods and are assigned with the help of potential energy distribution method. The first hyperpolarizability and infrared intensities are also reported. The geometrical parameters of the title compound obtained from XRD studies are in agreement with the calculated (DFT) values. The stability of the molecule arising from hyper-conjugative interaction and charge delocalization has been analyzed using NBO analysis. The HOMO and LUMO analysis are used to determine the charge transfer within the molecule. MEP was performed by the DFT method.

FT-IR, molecular structure, first order hyperpolarizability, HOMO and LUMO analysis, MEP and NBO analysis of 2-(4-chlorophenyl)-2-oxoethyl 3-nitrobenzoate.

2-(4-Chlorophenyl)-2-oxoethyl 3-nitrobenzoate is synthesized by reacting 4-chlorophenacyl bromide with 3-nitrobenzoic acid using a slight excess of potassium or sodium carbonate in DMF medium at room temperature. The structure of the compound was confirmed by IR and single-crystal X-ray diffraction studies. FT-IR spectrum of 2-(4-chlorophenyl)-2-oxoethyl 3-nitrobenzoate was recorded and analyzed. The crystal structure is also described. The vibrational wavenumbers were computed using HF and DFT methods and are assigned with the help of potential energy distribution method. The first hyperpolarizability and infrared intensities are also reported. The geometrical parameters of the title compound obtained from XRD studies are in agreement with the calculated (DFT) values. The stability of the molecule arising from hyper-conjugative interaction and charge delocalization has been analyzed using NBO analysis. The HOMO and LUMO analysis are used to determine the charge transfer within the molecule. MEP was performed by the DFT method.

Synthesis, molecular structure, FT-IR and XRD investigations of 2-(4-chlorophenyl)-2-oxoethyl 2-chlorobenzoate: a comparative DFT study.

2-(4-Chlorophenyl)-2-oxoethyl 2-chlorobenzoate has been synthesized, its structural and vibrational properties have been reported using FT-IR and single-crystal X-ray diffraction (XRD) studies. The conformational analysis, optimized geometric parameters, normal mode frequencies and corresponding vibrational assignments of the synthesized compound (C15H10Cl2O3) have been examined by means of Becke-3-Lee-Yang-Parr (B3LYP) density functional theory (DFT) method together with 6-31++G(d,p) basis set. Furthermore, reliable conformational investigation and vibrational assignments have been made by the potential energy surface (PES) and potential energy distribution (PED) analyses, respectively. Calculations are performed with two possible conformations. The title compound crystallizes in orthorhombic space group Pbca with the unit cell dimensions a=12.312(5) Å, b=8.103(3) Å, c=27.565(11) Å, V=2750.0(19) Å(3). B3LYP method provides satisfactory evidence for the prediction of vibrational wavenumbers and structural parameters.

Heteroaryl chalcones: design, synthesis, X-ray crystal structures and biological evaluation.

Chalcone derivatives have attracted increasing attention due to their numerous pharmacological activities. Changes in their structures have displayed high degree of diversity that has proven to result in a broad spectrum of biological activities. The present study highlights the synthesis of some halogen substituted chalcones 3(a-i) containing the 5-chlorothiophene moiety, their X-ray crystal structures and the evaluation of possible biological activities such as antibacterial, antifungal and reducing power abilities. The results indicate the tested compounds show a varied range of inhibition values against all the tested microbial strains. Compound 3c with a p-fluoro substituent on the phenyl ring exhibits elevated antimicrobial activity, whereas the compounds 3e and 3f displayed the least antimicrobial activities. The compounds 3d, 3e, 3f and 3i showed good ferric and cupric reducing abilities, and the compounds 3b and 3c showed the weakest reducing power in the series.

Structural correlation of some heterocyclic chalcone analogues and evaluation of their antioxidant potential.

A series of six novel heterocyclic chalcone analogues 4(a-f) has been synthesized by condensing 2-acetyl-5-chlorothiophene with benzaldehyde derivatives in methanol at room temperature using a catalytic amount of sodium hydroxide. The newly synthesized compounds are characterized by IR, mass spectra, elemental analysis and melting point. Subsequently; the structures of these compounds were determined using single crystal X-ray diffraction. All the synthesized compounds were screened for their antioxidant potential by employing various in vitro models such as DPPH free radical scavenging assay, ABTS radical scavenging assay, ferric reducing antioxidant power and cupric ion reducing antioxidant capacity. Results reflect the structural impact on the antioxidant ability of the compounds. The IC0 values illustrate the mild to good antioxidant activities of the reported compounds. Among them, 4f with a p-methoxy substituent was found to be more potent as antioxidant agent.

(Z)-N-[2-(N'-Hy-droxy-carbamimido-yl)phen-yl]acetamide.

The asymmetric unit of the title compound, C9H11N3O2, contains two mol-ecules (A and B), which exist in Z conformations with respect to their C=N double bond. The dihedral angles between the benzene ring and the pendant hy-droxy-carbamimidoyl and acetamide groups are 28.58 (7) and 1.30 (5)°, respectively, in mol-ecule A and 25.04 (7) and 27.85 (9)°, respectively, in mol-ecule B. An intra-molecular N-H⋯N hydrogen bond generates an S(6) ring in both mol-ecules. Mol-ecule A also features an intra-molecular C-H⋯O inter-action, which closes an S(6) ring. In the crystal, the mol-ecules are linked by N-H⋯O, N-H⋯N, O-H⋯O, O-H⋯N, C-H⋯O and C-H⋯N hydrogen bonds and C-H⋯π inter-actions, generating a three-dimensional network.

Ethyl 4-{[1-(2,4-dichloro-benz-yl)-1H-1,2,3-triazol-4-yl]meth-oxy}-8-(trifluoro-meth-yl)quinoline-3-carboxyl-ate.

In the title compound, C(23)H(17)Cl(2)F(3)N(4)O(3), the triazole ring makes dihedral angles of 50.27 (6) and 82.78 (7)° with the quinoline ring system and the dichloro-substituted benzene ring. The dihedral angle between the quinoline and dichloro-substituted benzene rings is 38.17 (4)°. In the crystal, mol-ecules are linked via C-H⋯N, C-H⋯F and C-H⋯O hydrogen bonds into a three-dimensional network. The crystal is further consolidated by C-H⋯π contacts to the triazole ring and inversion-related π-π inter-actions between the benzene and pyridine rings of quinoline systems [centroid-centroid distance = 3.7037 (7) Å].

1-[3-(4-Fluoro-phen-yl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl]ethanone.

In the title compound, C(17)H(15)FN(2)O, the pyrazoline ring adopts a flattened envelope conformation. The dihedral angle between the fluoro-substituted benzene ring and the phenyl ring is 69.20 (5)°. In the crystal, a pair of C-H⋯O hydrogen bonds link neighbouring mol-ecules, forming an inversion dimer. The crystal structure is further consolidated by C-H⋯π inter-actions and by a π-π inter-action with a centroid-centroid distance of 3.7379 (6) Å.

10a-Hy-droxy-9-(4-meth-oxy-phen-yl)-3,4,5,6,7,8a,9,10a-octa-hydro-1H-xanthene-1,8(2H)-dione.

In the title compound, C(20)H(22)O(5), the tetra-hydro-pyran, cyclo-hexene and cyclo-hexane rings of the xanthene ring system adopt half-chair, half-boat and chair conformations, respectively. The mean plane of the four roughly planar atoms of the tetra-hydro-pyran ring (r.m.s. deviation = 0.111 Å) forms a dihedral angle of 82.91 (4)° with the meth-oxy-benzene group. In the crystal, mol-ecules are linked via O-H⋯O and C-H⋯O hydrogen bonds into sheets lying parallel to the ac plane. The crystal is further consolidated by weak C-H⋯π inter-actions.

2-(4-Bromo-phen-yl)-N-(5-methyl-pyridin-2-yl)acetamide.

The asymmetric unit of the title compound, C(14)H(13)BrN(2)O, consists of two mol-ecules; the dihedral angles between the pyridine and benzene rings are 87.99 (9) and 84.28 (9)°. An intra-molecular C-H⋯O hydrogen bond generates an S(6) ring in each mol-ecule. In the crystal, mol-ecules are linked via N-H⋯N and C-H⋯O hydrogen bonds into a three-dimensional network. The crystal structure also features weak π-π stacking inter-actrions between the benzene rings [centroid-to-centroid distance = 3.6829 (12) Å].

(Z)-3-Benzyl-2-[(2-phenyl-cyclo-hex-2-en-yl)imino]-1,3-thia-zolidin-4-one.

The title compound, C(22)H(22)N(2)OS, exists in a Z configuration with respect to the N=C bond. The cyclo-hexene ring adopts a distorted sofa conformation. The thia-zolidine ring is essentially planar, with a maximum deviation of 0.030 (2) Å, and forms dihedral angles of 76.66 (6) and 74.55 (6)° with the terminal phenyl rings. The dihedral angle between the phenyl rings is 71.55 (7)°. In the crystal, a C-H⋯π inter-action is observed.

(Z)-3-(4-Bromo-phen-yl)-2-[(2-phenyl-cyclo-hex-2-en-1-yl)imino]-1,3-thia-zol-idin-4-one.

The title compound, C(21)H(19)BrN(2)OS, exists in a cis conformation with respect to the N=C bond [1.2602 (14) Å]. The cyclo-hexene ring adopts a distorted half-chair conformation and the C-N bond lies in an equatorial orientation. The thia-zolidine ring forms dihedral angles of 53.76 (7) and 57.22 (7)° with the benzene and bromo-substituted benzene rings, respectively. The dihedral angle between the benzene and bromo-substituted benzene rings is 76.06 (7)°. In the crystal, inversion dimers linked by pairs of C-H⋯O hydrogen bonds generate R(2) (2)(14) loops. The crystal is further consolidated by weak C-H⋯π inter-actions.

(Z)-3-(4-Chloro-phen-yl)-2-(2-phenyl-cyclo-hex-2-en-1-yl-imino)-thia-zolidin-4-one.

The title compound, C(21)H(19)ClN(2)OS, exists in a cis conformation with respect to the N=C bond [1.2608 (13) Å]. The cyclo-hexene ring adopts a distorted half-chair conformation. The thia-zolidine ring is close to being planar (r.m.s. deviation = 0.057 Å) and makes dihedral angles of 62.92 (6) and 56.32 (6)°, respectively, with the benzene ring and the chloro-substituted benzene ring. The dihedral angle between the benzene ring and the chloro-substituted benzene ring is 72.91 (6)°. In the crystal, mol-ecules are linked by C-H⋯O and C-H⋯N hydrogen bonds into undulating sheets lying parallel to the bc plane. The crystal is further consolidated by C-H⋯π inter-actions.

Dimethyl 4-[3-(4-meth-oxy-phen-yl)-1-phenyl-1H-pyrazol-4-yl]-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxyl-ate dihydrate.

In the title compound, C(27)H(27)N(3)O(5)·2H(2)O, the dihydro-pyridine ring adopts a flattened boat conformation. The central pyrazole ring is essentially planar [maximum deviation of 0.003 (1) Å] and makes dihedral angles of 50.42 (6) and 26.44 (6)° with the benzene rings. In the crystal, mol-ecules are linked via N-H⋯O, O-H⋯O, O-H⋯N and C-H⋯O hydrogen bonds into two-dimensional networks parallel to the bc plane. The crystal structure is further consolidated by weak C-H⋯π inter-actions.

[2,6-Bis(biphenyl-4-yl)-4-hy-droxy-4-(pyridin-2-yl)cyclo-hexane-1,3-di-yl]bis-[(pyridin-2-yl)methanone]-butan-2-one (1/1).

In the title solvate, C(47)H(37)N(3)O(3)·C(4)H(8)O, the cyclo-hexane ring adopts a chair conformation and the plane through its near coplanar atoms forms dihedral angles of 82.58 (7), 89.27 (7), 60.30 (8), 54.54 (7) and 72.03 (7)°, respectively, with the three pyridine rings and the two attached benzene rings. The rings of the biphenyl units are twisted from each other, making dihedral angles of 35.27 (7) and 45.41 (7)°. All the rings are in equatorial orientations in the cyclo-hexane ring, except for the C=O-bonded pyridine ring in position 1, which is axial. Intra-molecular O-H⋯N and C-H⋯O hydrogen bonds form one S(5) and three S(6) ring motifs. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds into a chain along the c axis. The crystal structure also features weak C-H⋯π inter-actions and aromatic π-π stacking [centroid-centroid distances = 3.5856 (10) and 3.7090 (9) Å].

(Z)-3-(4-Methyl-phen-yl)-2-[(2-phenyl-cyclo-hex-2-en-1-yl)imino]-1,3-thia-zol-idin-4-one.

The title compound, C(22)H(22)N(2)OS, exists in a cis conformation with respect to the N=C bond. The cyclo-hexene ring adopts a distorted sofa conformation. The thia-zolidine ring is essentially planar with a maximum deviation of 0.025 (2) Šand forms dihedral angles of 63.50 (7) and 57.52 (6)° with the benzene rings. In the crystal, mol-ecules are linked by C-H⋯O and C-H⋯N hydrogen bonds, generating R(2) (2)(8) ring motifs, and forming infinite chains along the c axis. The crystal is further consolidated by C-H⋯π inter-actions.

3-Chloro-4-methyl-quinolin-2(1H)-one.

The title compound, C(10)H(8)ClNO, is almost planar (r.m.s. deviation for the 13 non-H atoms = 0.023 Å). In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate R(2) (2)(8) rings. Weak aromatic π-π stacking inter-actions [centroid-centroid distance = 3.7622 (12) Å] also occur.

2,2-Diphenyl-N-(1,3-thia-zol-2-yl)acetamide.

In the title mol-ecule, C(17)H(14)N(2)OS, the mean plane of the acetamide group forms dihedral angles of 75.79 (5), 81.85 (6) and 12.32 (5)° with the two phenyl rings and the thia-zole ring, respectively. In the crystal, N-H⋯N hydrogen bonds link pairs of mol-ecules into inversion dimers with R(2) (2)(8) ring motifs. The crystal packing is further stabilized by C-H⋯π inter-actions and by π-π inter-actions with a centroid-centroid distance of 3.6977 (5) Å.

N-(3,4-Difluoro-phen-yl)-2,2-diphenyl-acetamide.

In the title compound, C(20)H(15)F(2)NO, the mean plane of the acetamide group makes dihedral angles of 88.26 (6), 78.30 (7) and 9.83 (6)° with the two terminal benzene rings and difluoro-substituted benzene ring, respectively. One F atom is disordered over two orientations rotated by 180°, with a site-occupancy ratio of 0.557 (2):0.443 (2). An intra-molecular C-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, mol-ecules are linked via N-H⋯O hydrogen bonds into chains along the c axis. The crystal structure is further consolidated by C-H⋯π inter-actions.

4-Methyl-benzoic acid-N'-[(E)-4-methyl-benzyl-idene]pyridine-4-carbohydrazide-water (1/1/1).

In the title hydrated 1:1 adduct, C(8)H(8)O(2)·C(14)H(13)N(3)O·H(2)O, the Schiff base mol-ecule exists in an E conformation with respect to the N=C bond [1.2843 (13) Å] and the dihedral angle between the pyridine ring and the benzene ring is 1.04 (5)°. In the crystal, mol-ecules are linked by N-H⋯O, C-H⋯O, O-H⋯O and O-H⋯N hydrogen bonds into sheets lying parallel to the ab plane. The crystal structure also features π-π inter-actions with centroid-centroid distances of 3.6224 (6) and 3.7121 (6) Å.