N-(4-Nitrophenyl)-2-{2-[3-(4-chlorophenyl)-5-[4-(propan-2-yl)phenyl]-4,5-dihydro-1H-pyrazol-1-yl]-4-oxo-4,5-dihydro-1,3-thiazol-5-yl}acetamide

In the present investigation, the synthesis and spectroscopic characterization of N-(4-nitrophenyl)-2-{2-[3-(4-chlorophenyl)-5-[4-(propan-2-yl)phenyl]-4,5-dihydro-1H-pyrazol-1-yl]-4-oxo-4,5-dihydro-1,3-thiazol-5-yl}acetamide (2) is performed. The title compound (2) is synthesized by the reaction of 3-(4-chlorophenyl)-5-[4-(propan-2-yl)phenyl]-4,5- dihydro-1H-pyrazole-1-carbothioamide (1) with N-(4-nitrophenyl)maleimide. The cyclization of title compound is evidenced by FT-IR, NMR, and LCMS data

1-{3-(4-Chlorophenyl)-5-[4-(propan-2-yl)phenyl]-4,5-dihydro-1H-pyrazol-1-yl}ethanone

In the title compound, C20H21ClN2O, the dihedral angles between the pyrazole ring (r.m.s. deviation = 0.049 Å) and the benzene and chlorobenzene rings are 84.65 (10) and 3.35 (10)°, respectively. In the crystal, inversion dimers linked by pairs of weak C—H...O interactions generate R22(16) loops. Weak π–π stacking interactions [centroid–centroid distance = 3.8490 (11) Å] are also observed

1-{3-(4-Chlorophenyl)-5-[4-(propan-2-yl)phenyl]-4,5-dihydro-1H-pyrazol-1-yl}butan-1-one

In the title compound, C22H25ClN2O, the pyrazole ring exhibits an envelope conformation with the methine C atom as the flap. The benzene rings are twisted by 3.3 (5) and 84.6 (5)° from the pyrazole mean plane, and are inclined to each other by 81.4 (4)°. In the crystal, pairs of weak C—H...O hydrogen bonds form centrosymmetric dimers with an R22(16) graph-set motif. C—H...π interactions link the dimers into columns propagating in [100]

(2E)-1-(4-Chlorophenyl)-3-[4-(propan-2-yl)phenyl]prop-2-en-1-one

In the title compound, C18H17ClO, the dihedral angle between the benzene rings is 53.5 (1)°. The mean plane of the prop-2-en-1-one group is twisted by 24.5 (8) and 33.5 (3)° from the chloro- and propanyl-substituted rings, respectively

1-{3-(4-Chlorophenyl)-5-[4-(propan-2-yl)phenyl]-4,5-dihydro-1H-pyrazol-1-yl}propan-1-one

In the title compound, C21H23ClN2O, the dihedral angle between the benzene rings is 83.2 (6)°, while the mean plane of the pyrazole ring [r.m.s. deviation = 0.043 (1) Å] makes dihedral angles of 3.4 (3) and 86.2 (1)° with the benzene rings. In the crystal, a pair of weak C—H...O interactions between the benzene ring and the propan-1-one group link the molecules into an inversion dimer with an R22(16) graph-set motif. In addition, a weak π–π stacking interaction [centroid–centroid distance = 3.959 (4) Å] connects the dimers into a tape running along [201]

A chalcone showing positional disorder, two related di­aryl­cyclo­hexenones showing enanti­omeric disorder and a related hy­dr­oxy­terphenyl, all derived from simple carbonyl precursors

Four compounds are reported, all of which lie along a versatile reaction pathway which leads from simple carbonyl compounds to terphenyls. (2E)-1-(2,4-Di­chloro­phen­yl)-3- [4-(prop-1-en-2-yl)phen­yl]prop-2-en-1-one, C18H14Cl2O, (I), prepared from 4-(prop-1-en-2-yl)benzaldehyde and 2,4-di­chloro­aceto­phenone, exhibits disorder over two sets of atomic sites having occupancies of 0.664 (6) and 0.336 (6). The related chalcone (2E)-3-(4-chloro­phen­yl)-1-(4-fluoro­phen­yl)prop-2-en-1-one reacts with acetone to produce (5RS)-3-(4-chloro­phen­yl)-5-[4-(propan-2-yl)phen­yl]cyclo­hex-2-en-1-one, C21H21ClO, (II), which exhibits enanti­omeric disorder with occupancies at the reference site of 0.662 (4) and 0.338 (4) for the (5R) and (5S) forms; the same chalcone reacts with methyl 3-oxo­butano­ate to give methyl (1RS,6SR)-4-(4-chloro­phen­yl)-6-[4-(propan-2-yl)phen­yl]-2-oxo­cyclo­hex-3-ene-1-carboxyl­ate, C23H23ClO3, (III), where the reference site contains both (1R,6S) and (1S,6R) forms with occupancies of 0.923 (3) and 0.077 (3), respectively. Oxidation, using 2,3-di­chloro-5,6-di­cyano-1,4-benzo­quinone, of ethyl (1RS,6SR)-6-(4-bromo­phen­yl)-4-(4-fluoro­phen­yl)-2-oxo­cyclo­hex-3-ene-1-carboxyl­ate, prepared in a similar manner to (II) and (III), produces ethyl 4′′-bromo-4-fluoro-5′-hy­droxy-1,1′:3′,1′′-terphenyl-4′-carboxyl­ate, C21H16BrFO3, (IV), which crystallizes with Z′ = 2 in the space group P[\overline{1}]. There are no significant inter­molecular inter­actions in the structures of compounds (I) and (II), but for the major disorder component of compound (III), the mol­ecules are linked into sheets by a combination of C—H⋯O and C—H⋯π(arene) hydrogen bonds. The two independent mol­ecules of com­pound (IV) form two different centrosymmetric dimers, one built from inversion-related pairs of C—H⋯O hydrogen bonds and the other from inversion-related pairs of C—H⋯π(arene) hydrogen bonds. Comparisons are made with related compounds