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, C19H17ClN2O2, the pyrazole ring is almost planar with a maximum deviation of 0.009 (3) Å and makes a dihedral angle of 8.96 (9)° with the oxazine ring. The dihedral angles between the pyrazole ring and the chlorine- and methoxy-substituted benzene rings are 50.95 (8) and 13.24 (9)°, respectively. An intermolecular C—H⋯N hydrogen bond links the molecules into infinite chains along the a axis. The crystal structure is further stabilized by C—H⋯π interactions.
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].
In the title compound, C18H11ClN6, the pyrrole, pyrimidine and tetrazole rings form a nearly planar fused trihetrocyclic system with an r.m.s. deviation of 0.0387 (13) Å, to which the 4-chlorophenyl group and the phenyl group are substituted at the 7 and 9 positions, respectively. The dihedral angles between the pyrrole ring and the 4-chlorophenyl and phenyl rings are 32.1 (4) and 7.87 (7)°, respectively. In the crystal, weak intermolecular C—H⋯N and C—H⋯Cl hydrogen bonds link the molecules into a layer parallel to the (001) plane. The layers are further connected by π–π stacking interactions [centroid–centroid distances: 3.8413 (8) and 3.5352 (8) Å]. Intramolecular C—H⋯N hydrogen bonds are also present.
In the title compound, C16H11ClN2O, the chloro-substituted phenyl ring is disordered over two positions with refined site occupancies of 0.503 (2) and 0.497 (2). The dihedral angle between the pyrazole and phenyl rings is 7.93 (7)°. The pyrazole ring also forms dihedral angles of 24.43 (9)° and 28.67 (9)° with the disordered chloro-substituted benzene ring. In the crystal, molecules are linked by intermolecular C—H⋯O hydrogen bonds, generating R
1(7) and R
2(10) ring motifs. π–π interactions between the pyrazole and phenyl rings [centroid–centroid distance = 3.758 (1) Å] further stabilize the crystal structure.
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 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.
In the title compound, C15H10ClNO3, a substituted chalcone, the 2-chlorophenyl and 4-nitrophenyl rings make a dihedral angle of 26.48 (6)°. The nitro group makes a dihedral angle of 11.64 (7)° with the plane of the benzene ring to which it is bound. Weak intramolecular C—H⋯O and C—H⋯Cl interactions involving the enone groups generate S(5) ring motifs, which help to stabilize the planarity of the 3-(2-chlorophenyl)prop-2-en-1-one segment of the molecule. In the crystal structure, adjacent molecules are stacked in a head-to-tail fashion into columns along the a axis by π–π interactions [centroid–centroid distance = 3.6955 (8) Å]. Neighbouring columns are linked by weak C—H⋯O 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.
The title compound, C15H10Cl2O, is a chalcone with 3-chlorophenyl and 4-chlorophenyl substituents bonded at the opposite ends of a propenone group, the biologically active region. The dihedral angle between mean planes of these two chloro-substituted benzene rings is 46.7 (7)° compared to 46.0 (1) and 32.4 (1)° in similar published sructures. The angles between the mean plane of the prop-2-en-1-one group and the mean planes of the 3-chlorophenyl and 4-chlorophenyl rings are 24.1 (2) and 29.63°, respectively. While no classical hydrogen bonds are present, weak intermolecular C—H⋯π-ring interactions are observed, which contribute to the stability of crystal packing.
In the title compound, C16H14ClN3O2, the 2,3-dihydro-1,3,4-oxadiazole ring [maximum deviation = 0.030 (1) Å] and the pyridine ring [maximum deviation = 0.012 (1) Å] are inclined slightly to one another, making a dihedral angle of 11.91 (5)°. The chloro-substituted phenyl ring is almost perpendicular to the 2,3-dihydro-1,3,4-oxadiazole and pyridine rings at dihedral angles of 86.86 (5) and 75.26 (5)°, respectively. In the crystal, π–π [centroid–centroid distance = 3.7311 (6) Å] and C—H⋯π interactions are observed.
In the title compound, C29H27ClN4O2, the six-membered ring of the pyridazine group is nearly planar [maximum deviation = −0.062 (2) Å] and its mean plane makes dihedral angles of 43.05 (9), 44.71 (10) and 72.57 (9)°, respectively, with the two phenyl and benzene rings. The piperazine ring has a chair conformation and its mean plane is almost perpendicular to the attached benzene ring, with a dihedral angle of 83.20 (16)°. In the crystal, molecules are linked via two pairs of C—H⋯O interactions, which result in the formation of chains propagating along [10-1]. Neighbouring chains are linked via C—H⋯π interactions.
In the title compound, C11H10ClN3S, the dihedral angle between the benzene and pyrimidine rings is 3.99 (4)°. In the crystal, intermolecular N—H⋯N hydrogen bonds link the molecules into ribbons of R
2(8) rings parallel to . Weak C—H⋯S contacts connect adjacent ribbons into a two-dimensional undulating layer-like structure extending parallel to (110). The benzene and pyrimidine rings of adjacent molecules have the offset face-to-face π–π stacking interactions in a zigzag fashion along the c axis, with perpendicular ring distances of 3.463 and 3.639 Å, and a dihedral angle between the planes of 3.99 (2)°. The distance between the ring centroids is 4.420 (2) Å.
In the title compound, C32H26Cl2N2O3, the piperidone ring adopts a chair conformation and the proline and pyrrolidine rings adopt envelope conformations. The indane ring system is essentially planar with an r.m.s. deviation of 0.011 Å for the non-H atoms. The dihedral angle between the two chloro-substituted benzene rings is 63.69 (10)°. Intramolecular C—H⋯O and N—H⋯O hydrogen bonds may influence the molecular conformation. In the crystal structure, molecules are connected into layers by weak intermolecular C—H⋯O hydrogen bonds.
In the title molecule, C24H21ClN4OS2, the central 1,2,4-triazole ring forms dihedral angles of 89.05 (9), 86.66 (9) and 82.70 (10)° with the chloro-substituted benzene ring, the methylsulfanyl-substituted benzene ring and the phenyl ring, respectively. In the crystal, molecules are linked into sheets parallel to (100) by intermolecular N—H⋯N and weak C—H⋯O hydrogen bonds.
In the title resonance conformer, C15H12ClNO4, the central C–N bond [1.297 (2) Å] has considerable double-bond character and the N–O bond [1.3215 (18) Å] indicates formal negative charge on the oxygen atom. Considerable deviations from co-planarity are evident in the molecule, with both benzene rings twisted out of the central C–C–N–C plane [the dihedral angle formed between the rings = 81.99 (8)°]. Similarly, the carboxylic acid residue occupies a position almost normal to the plane of the benzene ring to which it is connected [C—C—O—C torsion angle = −78.42 (17)°]. The most prominent intermolecular interactions involve the carboxylic acid the N+–O− residues with the O—H⋯O hydrogen bonds leading to helical supramolecular chains along the b axis. These chains are connected into layers via C–H⋯Ocarbonyl interactions and the layers are consolidated into the crystal structure by C–H⋯Cl contacts.
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.
The β-lactam ring of the title compound, C26H25ClN2O4, is nearly planar (r.m.s. deviation = 0.025 Å) and the morpholine ring adopts a chair conformation. The mean plane of the β-lactam ring makes dihedral angles of 21.6 (4), 84.4 (4) and 33.7 (4)° with the two benzene rings and the phenyl ring, respectively. The conformation of the title compound is stabilized by intramolecular C—H⋯O and O—H⋯N interactions. The crystal structure features C—H⋯π and aromatic π–π stacking interactions [centroid–centroid distances = 3.684 (4) and 3.883 (4) Å].
In the molecular structure of the title compound, C13H9Cl2NO, the amide N—C=O plane makes dihedral angles of 31.53 (8) and 36.23 (8)°, respectively, with the 4-chloro- and 2-chlorophenyl rings. The dihedral angle between the two benzene rings is 6.25 (8)°. The molecules are stacked in columns along the b axis through intermolecular N—H⋯O hydrogen bonds. The columns are further connected by weak C—H⋯O hydrogen bonds. The compound is not isomorphous with the fluoro analogue.
The asymmetric unit of the title compound, C21H13ClFNO2S, contains two independent molecules with similar conformations. In the molecules, the thiazole ring is essentially planar [maximum atomic deviations = 0.014 (4) and 0.023 (5) Å] and is oriented with respect to the fluorophenyl ring and chlorophenyl rings at 9.96 (18) and 70.39 (18)° in one molecule and at 7.50 (18) and 68.43 (18)° in the other; the dihedral angles between the fluorophenyl and chlorophenyl rings are 64.9 (2) and 64.6 (2)°, respectively. Intermolecular C—H⋯O and C—H⋯F hydrogen bonds stabilize the three-dimensional supramolecular architecture. Weak C—H⋯π and π–π interactions [centroid–centroid distance = 3.877 (3) Å] lead to a criss-cross molecular packing along the c axis.
In the title compound, C18H12Cl2N2O, the pyrazole ring is almost planar [r.m.s. deviation = 0.002 Å] while the two chlorophenyl rings are twisted out from the plane of the pyrazole ring, making dihedral angles of 5.3 (1) and 65.34 (4)°. In the crystal, centrosymmetric R
2(24) dimers are formed about crystallographic inversion centres through a pair of C—H⋯Cl interactions. These dimers are further linked through a C—H⋯O hydrogen bond, forming a C(8) chain extending along the a axis. C—H⋯π interactions are also observed.
In the title compound, C11H8ClN3O2, the presence of intramolecular N—H⋯O and C—H⋯N interactions help to establish an almost planar molecule [dihedral angle between the pyridine and benzene rings = 9.89 (8)° and r.m.s. deviation for all 17 non-H atoms = 0.120 Å]. Supramolecular tapes feature in the crystal packing whereby dimeric aggregates sustained by pairs of C—H⋯O interactions are connected by π–π interactions occurring between translationally related pyridine rings and between translationally related benzene rings along the b axis [centroid–centroid distance = length of b axis = 3.8032 (4) Å].
In the title compound, C14H9ClN2O, the quinazoline unit is essentially planar, with a mean deviation from the least-squares plane defined by the ten constituent ring atoms of 0.027 (2) Å. The dihedral angle between the mean plane of the quinazoline ring system and the 4-chlorophenyl ring is 44.63 (5)°. In the crystal, molecules are linked by intermolecular C—H⋯N and C—H⋯O hydrogen bonds, forming infinite chains of alternating R22(6) dimers and R22(14) ring motifs.
In the title molecule, C22H14ClN3, the triazoloisoquinoline ring system is approximately planar, with an r.m.s. deviation of 0.033 (2) Å and a maximum departure from the mean plane of 0.062 (1) Å for the triazole ring C atom, bonded to the benzene ring. The benzene and phenyl rings are twisted by 57.02 (6) and 62.16 (6)°, respectively, to the mean plane of the triazoloisoquinoline ring system. The molecule is stabilized by a weak intramolecular π–π interaction [centroid–centroid distance = 3.7089 (10) Å] between the benzene and phenyl rings. In the crystal structure, weak intermolecular C—H⋯N hydrogen bonds and C—H⋯π interactions link the molecules.
In the title compound, C26H22ClFO2, the cyclopropane ring makes dihedral angles of 45.7 (2), 49.0 (2) and 65.2 (2)° with the fluoro-substituted phenyl ring, the benzene ring and the chloro-substituted phenyl ring, respectively. The F and Cl atoms deviate by 0.0307 (11) and 0.0652 (6) Å, respectively, from the planes of the phenyl rings to which they are attached. In the crystal, molecules are linked by C—H⋯F hydrogen bonds, forming chains along the b axis.