Structural, Theoretical Analysis, and Molecular Docking of Two Benzamide Isomers. Halogen Bonding and Its Role in the Diverse Ways of Coupling with Protein Residues.

The crystal structures of two methoxyphenylbenzamide isomers are described, (Ph2Br) and (Ph3Br), with the general formula CHBrNO. This structural study revealed the presence of N-H-O and C-H-O hydrogen bonds, Br-Br halogen bonds, C-H-π, and C-Br-π molecular contacts, showing in both compounds, a central C1-C7(O1)-N1(H1)-C8 amide segment, to be almost linear. The close proximity between the Br1 and O1 in Ph2Br showed that its interatomic distance was less than the sum of their VDW radii, generating an increase in the electrostatic potential in the O1 region, making possible the appearance of the so-called σ and π-holes on bromine.

Synthesis, spectroscopic characterization, structural studies, thermal analysis and molecular docking of N-(2-methyl-5-nitrophenyl)-4-(pyridin-2-yl)pyrimidin-2-amine, a precursor for drug design against chronic myeloid leukemia.

The synthesis, crystal structure and spectroscopic and electronic properties of N-(2-methyl-5-nitrophenyl)-4-(pyridin-2-yl)pyrimidin-2-amine (NPPA), CHNO, a potential template for drug design against chronic myelogenous leukemia (CML), is reported. The design and construction of the target molecule were carried out starting from the guanidinium nitrate salt (previously synthesized) and the corresponding enaminone. X-ray diffraction analysis and a study of the Hirshfeld surfaces revealed important interactions between the nitro-group O atoms and the H atoms of the pyridine and pyrimidine rings.

Synthesis, spectroscopic (FT-IR and UV-Vis), crystallographic and theoretical studies, and a molecular docking simulation of an imatinib-like template.

The aim of the present study was to report the crystal structure and spectroscopic, electronic, supramolecular and electrostatic properties of a new polymorph of 4-(pyridin-2-yl)pyrimidin-2-amine (CHN). The compound was synthesized under microwave irradiation. The single-crystal X-ray structure analysis revealed an angle of 13.

Catalyst- and solvent-free synthesis of 2-fluoro-N-(3-methylsulfanyl-1H-1,2,4-triazol-5-yl)benzamide through a microwave-assisted Fries rearrangement: X-ray structural and theoretical studies.

An efficient approach for the regioselective synthesis of (5-amino-3-methylsulfanyl-1H-1,2,4-triazol-1-yl)(2-fluorophenyl)methanone, CHFNOS, (3), from the N-acylation of 3-amino-5-methylsulfanyl-1H-1,2,4-triazole, (1), with 2-fluorobenzoyl chloride has been developed. Heterocyclic amide (3) was used successfully as a strategic intermediate for the preparation of 2-fluoro-N-(3-methylsulfanyl-1H-1,2,4-triazol-5-yl)benzamide, CHFNOS, (4), through a microwave-assisted Fries rearrangement under catalyst- and solvent-free conditions. Theoretical studies of the prototropy process of (1) and the Fries rearrangement of (3) to provide (4), involving the formation of an intimate ion pair as the key step, were carried out by density functional theory (DFT) calculations.

Crystal structure of N-(2-hy-droxy-5-methyl-phen-yl)benzamide.

In the title compound, C14H13NO2, the mean plane of the non-H atoms of the central amide fragment C-N-C(=O)-C (r.m.s.

Crystal structure of 4-formyl-2-nitro-phenyl 4-chloro-2-nitro-benzoate.

In the title compound, C14H7ClN2O7, the central ester moiety is essentially planar, with an r.m.s.

Crystal structure of 2-fluoro-N-(1,3-thia-zol-2-yl)benzamide.

In the title compound, C10H7FN2OS, the mean plane of the central amide fragment (r.m.s.

Crystal structure of 2-(4-chloro-benzamido)-benzoic acid.

In the title mol-ecule, C14H10ClNO3, the amide C=O bond is anti to the o-carb-oxy substituent in the adjacent benzene ring, a conformation that facilitates the formation of an intra-molecular amide-N-H⋯O(carbon-yl) hydrogen bond that closes an S(6) loop. The central amide segment is twisted away from the carb-oxy- and chloro-substituted benzene rings by 13.93 (17) and 15.

Crystal structure of 3-chloro-N-(2-nitro-phen-yl)benzamide.

In the title compound, C13H9ClN2O3, the mean plane of the central amide fragment (r.m.s.

Crystal structure of 2-methyl-3-nitro-benzoic anhydride.

The title mol-ecule, C16H12N2O7, lies on a twofold rotation axis which bis-ects the central O atom. The dihedral angle between two symmetry-related benzene rings is 48.54 (9)°.

Crystal structure of 2-nitro-N-(2-nitro-phen-yl)benzamide.

In the title compound, C13H9N3O5, the mean plane of the non-H atoms of the central amide fragment C-N-C(=O)-C [r.m.s.

Crystal structure of 2-nitro-N-(5-nitro-1,3-thia-zol-2-yl)benzamide.

In the title compound, C10H6N4O5S, the mean plane of the non-H atoms of the central amide fragment C-N-C(=O)-C [r.m.s.

Crystal structure of (±)-3-[(benzo[d][1,3]dioxol-5-yl)meth-yl]-2-(3,4,5-tri-meth-oxy-phen-yl)-1,3-thia-zolidin-4-one.

In the title thia-zolidine-4-one derivative, C20H21NO6S, the central thia-zolidine ring is essentially planar (r.m.s.

2,4,6-Tri-nitro-phenyl 3-bromo-benzoate.

In the title picryl-substituted ester, C13H6BrN3O8, the mean plane of the central ester C-O-C(=O)-C fragment (r.m.s.

2-[(1-Oxidopyridin-4-yl)sulfan-yl]benzoic acid.

In the title compound, C12H9NO3S, the dihedral angle between the pyridine and benzene rings is 83.93 (7)°. In the crystal, pairs of O-H⋯O hydrogen bonds link the molecules, forming inversion dimers with graph-set notation R 2 (2)(22).

N-(2-Nitro-phen-yl)thio-phene-2-carbox-amide.

The title compound, C11H8N2O3S, shows two mol-ecules per asymmetric unit, with the dihedral angles between the benzene and thio-phene rings of 13.53 (6) and 8.50 (5)° being a notable difference between them.

2,4,6-Tri-nitro-phenyl 4-bromo-benzoate.

In the title benzoate derivative, C13H6BrN3O8, the benzene rings form a dihedral angle of 80.90 (9)°. The ester moiety forms dihedral angles of 3.

3-(Di-phenyl-amino)-isobenzo-furan-1(3H)-one.

In the title isobenzo-furan-one derivative, C20H15NO2, the planar fused-ring system (r.m.s.

4-Bromo-N-(2-nitro-phen-yl)benzamide.

The title nitro-phenyl benzamide, C13H9BrN2O3, with two mol-ecules in the asymmetric unit, has dihedral angles of 16.78 (15) and 18.87 (14)° between the benzene rings.

4-Formyl-2-nitro-phenyl benzoate.

In the title nitroaryl benzoate derivative, C14H9NO5, the aromatic rings form a dihedral angle of 46.37 (8)°. The central ester moiety, -C-(C=O)-O-, is essentially planar (r.

3,4-Di-methyl-phenyl benzoate.

In the title compound, C15H14O2, the terminal rings form a dihedral angle of 52.39 (4)°. The mean plane of the central ester group [r.