The asymmetric unit of the title compound, C21H23ClN4S, contains nine crystallographically independent molecules, labelled A to I. The orientation of the 2-[4-(2-methylpropyl)phenyl]ethyl unit with respect to the rest of the molecule is significantly different in molecules E, F, H and I compared to the other independent molecules. The isobutyl group of molecule B is disordered over two orientations, with occupancies of 0.764 (7) and 0.236 (7). The benzene rings of the chlorophenyl and methylpropylphenyl units form dihedral angles of 21.90 (11) and 71.47 (11)°, respectively, with the triazole ring in molecule A [9.15 (11) and 80.37 (11)° in B, 7.14 (11) and 84.06 (11)° in C, 25.76 (11) and 76.59 (11)° in D, 13.68 (11) and 76.82 (10)° in E, 8.38 (11) and 69.77 (10)° in F, 30.34 (11) and 78.12 (11)° in G, 21.20 (11) and 71.58 (10)° in H, and 27.65 (11) and 65.23 (11)° in I]. In each independent molecule, a C—H⋯S hydrogen bond is observed. The crystal packing is stabilized by N—H⋯S and C—H⋯S hydrogen bonds, and by C—H⋯π interactions involving the methylpropylphenyl ring.
The title compound, C24H19ClN2, crystallizes with two independent molecules in the asymmetric unit. The prop-2-enyl substituents on the imidazole rings adopt similar conformations in the two molecules. The 4-and 5-substituted phenyl rings and the benzene ring make dihedral angles of 67.06 (8), 5.61 (8) and 41.09 (8)°, respectively, with the imadazole ring in one molecule and 71.53 (8), 28.85 (8) and 41.87 (8)°, respectively, in the other. The crystal structure features C—H⋯π interactions and weak π–π stacking interactions [centroid–centroid distances = 3.6937 (10) and 4.0232 (10) Å] between the chlorophenyl rings, which form a three-dimensional supramolecular structure.
The molecule in the structure of the title compound, C15H11ClN2OS, displays two planar residues [r.m.s. deviation = 0.014 Å for the benzimidazole residue, and the ketone group is co-planar with the benzene ring to which it is attached forming a O—C—C—C torsion angle of −173.18 (14) °] linked at the S atom. The overall shape is based on a twisted V, the dihedral angle formed between the two planes being 82.4 (2) °. The amine-H atom is bifurcated, forming N—H⋯O and N—H⋯S hydrogen bonds leading to dimeric aggregates. These are linked into a supramolecular chain along the c axis via C—H⋯π hydrogen bonds. Chains form layers in the ab plane being connected along the c axis via weak π–π interactions [3.9578 (8) Å] formed between centrosymmetrically related chloro-substituted benzene rings.
In the crystal structure of the title compound, C11H9ClN4O3, pairs of N—H⋯N(imidazole) hydrogen bonds connect the molecules into centrosymmetric dimers, which are further connected by N—H⋯O(carbamoyl) hydrogen bonds into C(4) chains along . Interplay of these two kinds of hydrogen bonds connect the molecules into layers perpendicular to . The imidazole [maximum deviation 0.0069 (9) Å] and phenyl rings are inclined at a dihedral angle of 58.44 (6)°; the nitro group is almost coplanar [dihedral angle 5.8 (2)°] with the imidazole ring while the carbamoyl group is almost perpendicular [70.15 (13)°] to it.
In the title compound, C15H10BrClO, the molecule adopts an E configuration with respect to the C=C double bond and the dihedral angle between the aromatic ring planes is 3.98 (16)°. In the crystal, inversion dimers linked by pairs of C—H⋯O bonds are seen and weak π–π stacking [centroid–centroid separation = 3.8776 (19) Å] may further consolidate the structure. The crystal studied was a non-merohedral twin with a ratio of the twin components of 0.9093 (13):0.0907 (13). The twin operation is a twofold rotation around c*.
In the structure of the title compound, C18H15ClN4O4S, the dihedral angle between the two benzene rings is 1.4 (3)°. The angle between the phenyl ring and thiadiazole ring is 5.8 (4)°. The conformations of the N—H and C=O bonds are anti with respect to each other. In the crystal structure, molecules are linked by intermolecular O—H⋯N, N—H⋯O and O—H⋯O hydrogen bonds, forming a three-dimensional network.
In the title molecule, C15H11ClO2, the mean planes of the benzene and phenyl rings are inclined at 69.06 (11)° with respect to each other. The crystal structure is stablized by strong intermolecular O—H⋯O hydrogen bonds between the acid groups of pairs of molecules related by inversion centers.
In the title compound, C20H21ClN2O2, the ethyl 1H-benzimidazole-5-carboxylate ring system, excluding the methylene and methyl H atoms, is almost planar, with a maximum deviation of 0.055 (1) Å, and makes a dihedral angle of 40.63 (4)° with the benzene ring. The sec-butyl group is disordered over two positions, with refined site occupancies of 0.855 (4) and 0.145 (4). In the crystal, molecules are linked into chains along  via intermolecular C—H⋯O hydrogen bonds and are further interconnected by C—H⋯Cl interactions into two-dimensional networks parallel to (001). The crystal structure is further consolidated by C—H⋯π interactions.
In the title compound, C26H16ClN3O3, the dihedral angle between the anthracene mean plane and imidazole ring is 64.75 (2)°. In the crystal, π–π interactions between anthracene fragments lead to the formation of stacks of molecules propagating in . The short distance between the carbonyl groups of symmetry-related molecules [C⋯O = 2.985 (2) Å] indicates the existence of dipole–dipole interactions. The crystal packing also exhibits short intermolecular contacts between the nitro groups and Cl atoms [Cl⋯O = 3.181 (2) Å].
Two independent molecules comprise the asymmetric unit of the title compound, C20H16ClNO, which differ in the orientation of the chalcone residue with respect to the quinoline ring [the C—C—C(=O)—C torsion angles are 69.5 (2) and 86.0 (2)°]. The configuration about each of the ethylene bonds [1.342 (2) and 1.338 (2) Å] is E. The three-dimensional crystal structure is stabilized by a combination of C—H⋯O, C—H⋯N, C—H⋯π interactions and π–π contacts between the independent molecules [Cg(C6 of quinoline)⋯Cg(C6 of quinoline) = 3.6719 (11) Å].
In the title molecule, C22H15Cl2NO, the dihedral angles between the central aromatic ring and the N- and C=O-bonded rings are 43.13 (13) and 0.80 (14)°, respectively. The dihedral angle between the terminal rings is 43.15 (14)°. The major twist occurs about the Car—N bond [Car—Car—N=C = 42.3 (4)°; ar is aromatic].
The asymmetric unit of the 1:4 title co-crystal of 2-amino-4-(4-chlorophenyl)-5,6-dihydrobenzo[h]quinoline-3-carbonitrile and 3-amino-1-(4-chlorophenyl)-9,10-dihydrophenanthrene-2,4-dicarbonitrile, 0.2C20H14ClN3·0.8C22H14ClN3, has the atoms of the fused-ring system and those of the amino, cyano and chlorophenyl substitutents overlapped. The fused-ring system is buckled owing to the ethylene linkage in the central ring. There are two independent overlapped molecules in the asymmetric unit. In one independent molecule, the two flanking aromatic rings are twisted by 24.4 (1)° and the ring of the chlorophenyl substituent is twisted by 87.3 (1)° relative to the amino- and cyano-bearing aromatic ring. In the second molecule, the respective dihedral angles are 26.1 (1) and 57.8 (1)°. The two independent molecules are linked by N—H⋯N hydrogen bonds into dimers.
The asymmetric unit of the title compound, C17H10ClF2N3O, contains three independent molecules. In each molecule, the C=C bond has a cis conformation with respect to the triazole and chlorophenyl groups. The dihedral angles formed by the triazole ring with the diflurophenyl and chlorophenyl benzene rings, respectively, are 20.10 (14) and 73.22 (15), 25.31 (15) and 84.44 (15), and 16.44 (13) and 61.72 (14)° in the three molecules while the dihedral angles between the benzene rings are 66.54 (13), 85.82 (12) and 58.37 (12)°.
The title compound, C15H12ClNO, a substituted chalcone, adopts an E configuration with respect to the C=C bond of the enone unit. The molecule is not planar, as can be seen from the dihedral angle of 28.9 (2)° between the two rings which are twisted from each other. The enone segment of the molecule is not coplanar with the chlorophenyl ring, making a dihedral angle of 23.4 (3)° with it. The amino group is also not coplanar with the ring to which it is bound, making a dihedral angle of 35 (4)°. In the crystal structure, adjacent molecules are linked by N—H⋯O interactions into one-dimensional infinite chains along the c axis, and are further stacked as one-dimensional zigzag chains down the b axis, forming two-dimensional extended networks parallel to the bc plane.
The asymmetric unit of the title compound, C21H25ClN2O, contains four crystallographically independent molecules, which differ mainly in the orientation of the isobutyl groups. The benzene rings are almost orthogonal to each other, forming dihedral angles of 87.40 (6), 88.69 (6), 84.88 (6) and 85.12 (6)° in the four molecules. The crystal structure is stabilized by intermolecular N—H⋯O and C—H⋯O hydrogen bonds, together with C—H⋯π interactions.
The title compound, C16H13ClO2, adopts an E configuration with respect to the double bond of the propenone unit. The two benzene rings are twisted slightly from each other, making a dihedral angle of 7.14 (5)°. The molecules are arranged in stacks, in which adjacent molecules are related by inversion symmetry and form π–π interactions with a centroid–centroid distance of 3.7098 (6) Å. C—H⋯O and C—H⋯π interactions are formed between neighbouring molecules.
In the molecule of the title compound, C26H23ClN4O2·C3H7NO·2H2O, the indole and dihydropyridine rings are planar and make a dihedral angle of 89.86 (7)°. The dihydropyridine ring forms a dihedral angle of 79.95 (7)° with the attached benzene ring. In the crystal structure, intermolecular N—H⋯O and O—H⋯O hydrogen bonds link the molecules. Intermolecular C—H⋯N and C—H⋯Cl interactions are also present.
In the title compound, C28H24ClNO3, the dihedral angles between the central benzene ring and the indole ring system and the chlorobenzene ring are 70.81 (5) and 78.62 (5)°, respectively. The molecular structure is stabilized by a weak intramolecular C—H⋯O interaction. In the crystal, pairs of C—H⋯O hydrogen bonds link the molecules into inversion dimers with an R
In the imidazo[2,1-b][1,3]thiazole group of the title compound, C21H17ClN4O2S, the dihedral angle between the thiazole and imidazole rings is 1.9 (2)°. The mean plane of this group makes dihedral angles of 5.5 (2) and 39.9 (2)° with the benzene rings of the chlorophenyl and methoxyphenyl groups, respectively. The dihedral angle between these two benzene rings is 34.4 (2)°. In the crystal, molecules are connected to each other by intermolecular N—H⋯O hydrogen bonds along the b axis, generating a C(4) chain. Weak C—H⋯π interactions also occur.
The title molecule, C16H13ClO2, is trans with respect to the C=C double bond. The dihedral angles between the mean plane of the prop-2-en-1-one unit and those of the 3-chloro- and 4-methoxy-substituted benzene rings are 20.93 (9) and 20.42 (10)°, respectively, and the dihedral angle between the mean planes of the two benzene rings is 40.96 (5)°. The crystal structure is stabilized by weak intermolecular C—H⋯O hydrogen bonds, forming chains along the b axis.
The title compound, C16H13ClO, adopts an E configuration with respect to the C=C double bond of the propenone unit. The dihedral angle between the two benzene rings is 45.9 (2)°. In the crystal structure, molecules are arranged into sheets parallel to the ac plane and the sheets are stacked along the b axis. This arrangement is stabilized by weak intermolecular C—H⋯π interactions involving both aromatic rings.
In the title compound, C18H17ClN2O2, the benzene rings form dihedral angles of 6.69 (6) and 74.88 (5)° with the 4,5-dihydro-1H-pyrazole ring. The benzene rings form a dihedral angle of 76.67 (5)° with each other. In the crystal, molecules are linked via bifurcated (C,C)–H⋯O hydrogen bonds into chains along . The crystal structure is further consolidated by C—H⋯π interactions.
The title molecule, C14H11ClN4O4, is in an E configuration and is twisted with the dihedral angle between the two benzene rings being 38.48 (8)°. The ethylidenehydrazine plane makes dihedral angles of 6.03 (10) and 44.04 (11)°, respectively, with the dinitro- and chloro-substituted benzene rings. The two nitro groups are essentially coplanar with the bound benzene ring, making dihedral angles of 0.9 (2) and 1.65 (18)°. An intramolecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, molecules are linked by a weak C—H⋯O interaction into a chain along the c axis. The chains are further stacked along the b axis by a π–π interaction with a centroid–centroid distance of 3.6088 (10) Å.
In the title compound, C21H14ClN3O5, an intramolecular C—H⋯O hydrogen bond generates an S(7) ring motif and the furan and pyrazole rings are almost coplanar, making a dihedral angle of 1.98 (5)°. The pyrazole ring is inclined at dihedral angles of 47.59 (4) and 7.27 (4)° to the chlorophenyl and methoxyphenyl groups, respectively. The nitro group is almost coplanar to its attached furan ring [dihedral angle = 2.03 (12)°]. In the crystal, intermolecular C—H⋯O hydrogen bonds link the molecules into a three-dimensional network. The crystal structure also features short intermolecular O⋯N [2.8546 (12) Å] and Cl⋯O [3.0844 (9) Å] contacts as well as aromatic π–π stacking interactions [centroid–centroid distance = 3.4367 (6) Å].
In the title compound, C18H18ClN5O3, the hydrazinecarboxamide N—N—C(O)—N unit is nearly planar [maximum deviation = 0.074 (2) Å] and is inclined at a dihedral angle of 57.43 (7)° with respect to the plane of the attached benzene ring. The chlorophenyl group makes dihedral angles of 19.71 (7) and 34.07 (6)° with the pyrazole and benzene rings, respectively. In the crystal, pairs of N—H⋯O hydrogen bonds link the molecules into inversion dimers that are further linked into chains along the a-axis direction by N—H⋯N hydrogen bonds. In addition, π–π stacking interactions are observed between benzene rings [centroid–centroid distance = 3.680 (1) Å].