2-[(1,3-Benzo­thia­zol-2-yl)imino­meth­yl]-6-meth­oxy­phenol: a new monoclinic polymorph

The title compound, C₁₅H₁₂N₂O₂S, is a P2₁/c polymorph of a previously reported P2₁/n polymorph [Büyükgüngör et al. (2004). Acta Cryst. E60, o1414–o1416]. The dihedral angle between the benzo­thia­zole (r.m.s. deviation = 0.010 Å) and the benzene ring of 7.86 (6)° compares with 10.76 (10)° in the literature structure. The meth­oxy substituent is almost coplanar with the benzene ring to which it is attached [C—O—C—C torsion angle = 178.31 (14)°] and the conformation about the imine bond [1.287 (2) Å] is E. There is an intra­molecular O—H...N hydrogen bond and the hy­droxy O and thio­ether S atoms are syn. In the crystal, columns are formed along the b axis as centrosymmetric dimeric aggregates, mediated by C—H...O inter­actions and linked by π–π inter­actions between the thia­zole and benzene rings [centroid-to-centroid distance = 3.8256 (10) Å].

(2E)-3-(6-Chloro-2-meth­oxy­quinolin-3-yl)-1-(2,4-di­methyl­quinolin-3-yl)prop-2-en-1-one

The mol­ecule of the title compound, C₂₄H₁₉ClN₂O₂, is bent, with the dihedral angle between the terminal quinoline ring systems being 63.30 (5)°. The quinolinyl residues are connected by an almost planar prop-2-en-1-one bridge (r.m.s. deviation = 0.022 Å), with the dihedral angles between this plane and the appended quinolinyl residues being 75.86 (7) and 38.54 (7)°. The C atom of the meth­oxy group is close to coplanar with its attached ring [deviation = 0.116 (2) Å]. In the crystal, a three-dimensional architecture is constructed by meth­yl–carbonyl C—H...O inter­actions and π–π inter­actions between centrosymmetrically related quinolinyl residues [centroid-to-centroid separations 3.5341 (10) and 3.8719 (9) Å].

(2E)-3-(2-Chloro-8-methyl­quinolin-3-yl)-1-(2,4-di­methyl­quinolin-3-yl)prop-2-en-1-one

In the mol­ecule of the title compound, C₂₄H₁₉ClN₂O, the terminal quinolinyl residues are close to perpendicular to each other [dihedral angle 83.72 (4)°]. The quinolinyl residues are connected by and inclined to the prop-2-en-1-one bridge, with the C_ar—C_ar—C—C (ar = aromatic) torsion angles being 71.01 (17) and 20.6 (2)°. The crystal structure features phen­yl–carbonyl C—H...O inter­actions and π–π inter­actions between centrosymmetrically related quinolinyl residues [3.5341 (10) and 3.8719 (9) Å], which together lead to a three-dimensional architecture.

(2E)-3-(2-Chloro-8-methyl­quinolin-3-yl)-1-(2-methyl-4-phenyl­quinolin-3-yl)prop-2-en-1-one

In the title compound, C₂₉H₂₁ClN₂O, there is a twist in the bridging prop-2-en-1-one group [C=C—C=O torsion angle = 22.7 (2)°]. The quinolinyl residues form a dihedral angle of 86.92 (4)°, indicating an almost perpendicular relationship. In the crystal, supra­molecular layers in the bc plane are stabilized by C—H...π and π–π inter­actions [centroid–centroid distance = 3.4947 (7) Å].

(2E)-3-(6-Chloro-2-meth­oxy­quinolin-3-yl)-1-(2-methyl-4-phenyl­quinolin-3-yl)prop-2-en-1-one acetone monosolvate

In the title solvate, C₂₉H₂₁ClN₂O₂·C₃H₆O, a prop-2-en-1-one bridge links two quinolinyl residues; the latter are almost perpendicular [dihedral angle = 78.27 (6)°]. The dihedral angle between the quinonyl ring system and its pendant phenyl group is 59.78 (8)°. A small twist in the bridging prop-2-en-1-one group is noted [O=C—C=C torsion angle = −10.6 (3)°]. In the crystal, a three-dimensional architecture arises as a result of C—H...O and π–π stacking [centroid–centroid distances = 3.5504 (12)–3.6623 (12) Å].