The title compound, C12H13ClN2O2, crystallizes with two independent but very similar molecules (A and B) in the asymmetric unit. The pyrazole ring in each molecule has an envelope conformation. The dihedral angle between the pyrazole ring mean plane and the benzene ring is 86.07 (14)° in A and 85.99 (14)° in B. In the crystal, the A and B molecules are linked via a pair of O—H⋯O hydrogen bonds, forming dimers. These dimers are further linked via C—H⋯O interactions to form –A–B–A–B– chains propagating along the c-axis direction.
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.
In the title compound, C22H19ClN2O3S, the dihedral angle between the mean planes of the thiophene ring and the chlorophenyl and hydroxyphenyl rings are 70.1 (1) and 40.2 (4)°, respectively. The benzene rings are twisted with respect to each other by 88.9 (3)°. The imine bond lies in an E conformation. Intramolecular O—H⋯N and N—H⋯O hydrogen bonds each generate S(6) ring motifs. In the crystal, weak C—H⋯O interactions link the molecules, forming chains along the c axis and zigzag chains along the b axis, generating sheets lying parallel to (100).
crystal structure; thiophene derivatives; Schiff bases; hydrogen bonding
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 R
2(16) loops. Weak π–π stacking interactions [centroid–centroid distance = 3.8490 (11) Å] are also observed.
The asymmetric unit of the title compound, C18H18ClN3OS·C2H5OH, comprises a pyrazoline derivative and an ethanol solvent molecule. In the molecule of the pyrazoline derivative, the pyrazole ring adopts an envelope conformation with the C atom bearing the ethoxyphenyl substituent as the flap. The dihedral angle between the benzene rings is 74.22 (7)°. The ethoxy group is coplanar with the attached benzene ring [C—O—C—Cmethyl = 175.50 (11)° and r.m.s. deviation = 0.0459 (1) Å for the nine non-H atoms]. In the crystal, the pyrazoline molecules are linked by N—H⋯Oethoxy hydrogen bonds into chains along the c axis and are further linked with the solvent ethanol molecules by N—H⋯Oethanol and Oethanol—H⋯S hydrogen bonds. C—H⋯π interactions are also present.
In the title compound, C16H11ClN2O2, the pyrazole ring makes dihedral angles of 11.88 (13) and 22.33 (13)° with the 3-chloro-2-hydroxybenzene group and phenyl rings, respectively. The phenolic hydroxy group forms an intramolecular O—H⋯N hydrogen bond with the imine N atom of the pyrazole unit. The formyl group is virtually coplanar with the pyrazole ring [dihedral angle = 4.5 (19)°] and acts as an acceptor in an intramolecular C—H⋯O hydrogen bond closing seven-membered ring. In the crystal, adjacent molecules are linked through C—H⋯O hydrogen bonds into infinite chains along the b axis.
In the title compound, C15H11ClO2, the dihedral angle between the mean planes of the chlorobenzene and hydroxybenzene rings is 6.5 (6)°. The mean plane of the prop-2-en-1-one group makes an angle of 18.0 (1)° with the hydroxyphenyl ring and 11.5 (1)° with the chlorophenyl ring. The crystal packing is stabilized by intermolecular O—H⋯O hydrogen bonds, weak C—H⋯O, C—H⋯π and π–π stacking interactions [centroid–centroid distances = 3.7771 (7) and 3.6917 (7) 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].
In the title compound, C20H21ClN2O2, the benzene rings form dihedral angles of 6.35 (5) and 81.82 (5)° with the mean plane of the 4,5-dihydro-1H-pyrazole ring (r.m.s. deviation = 0.145 Å). This latter ring adopts an envelope conformation with the CH grouping as the flap. The dihedral angle between the benzene rings is 75.63 (4)°. In the crystal, molecules are linked by C—H⋯Cl and C—H⋯O hydrogen bonds into chains along [-201]. The crystal structure also features C—H⋯π interactions.
In the title molecule, C24H18ClNO6S, the heterocyclic thiazine ring adopts a half-chair conformation with the S and N atoms displaced by 0.406 (5) and 0.444 (5) Å, respectively, on opposite sides of the mean plane formed by the remaining ring atoms. The methoxybenzoyl and the chlorophenyl rings lie roughly parallel to each other, with a dihedral angle between the mean planes of these rings of 8.86 (10)°. The molecular structure is consolidated by intramolecular O—H⋯O and C—H⋯O interactions and the crystal packing is stabilized by intermolecular O—H⋯O and C—H⋯Cl hydrogen bonds.
In the title compound, C20H13ClN2O2S, the chlorophenyl, phenyl and thienoyl rings are oriented at dihedral angles 17.84 (7), 53.13 (8) and 34.03 (8)°, respectively, to the central pyrazole ring. An intramolecular O—H⋯O hydrogen bond occurs. In the crystal, pairs of bifurcated O—H⋯O hydrogen bonds link molecules into inversion dimers with R
2(12) graph-set motifs.
In the title pyrazoline derivative, C14H12ClN3S2, the thiophene ring is disordered over two orientations with a refined site-occupancy ratio of 0.832 (4):0.168 (4). The pyrazoline ring adopts an envelope conformation with the C atom linking the thiophene ring at the flap. The dihedral angles between the benzene ring and the major and minor components of the thiophene ring are 88.6 (3) and 85.6 (15)°, respectively while the dihedral angle between the disorder components of the ring is 3.1 (16)°. The mean plane of the pyrazoline ring makes dihedral angles of 11.86 (13), 80.1 (3) and 83.0 (15)°, respectively, with the benzene ring, and the major and minor components of the thiophene ring. An intramolecular N(amide)—H⋯N(pyrazoline) hydrogen bond generates an S(5) ring motif. In the crystal, molecules are linked by weak C—H⋯S and N(amide)—H⋯S interactions into a tape along . C—H⋯π interactions are also observed.
In the title compound, C19H15ClN2O2, the pyrazole ring is almost planar (r.m.s. deviation = 0.002 Å) and subtends dihedral angles of 5.31 (16) and 1.86 (16)° with the phenyl and chlorobenzene rings, respectively. An intramolecular O—H⋯O hydrogen bond closes an S(6) ring and a short C—H⋯O contact is also observed. In the crystal, molecules are linked by weak C—H⋯O interactions to generate (001) sheets. Weak aromatic π–π interactions between the chlorobenzene and pyrazole rings, with a centroid–centroid distance of 3.7956 (17) Å are also observed.
crystal structure; pyrazole; hydrogen bonding; π–π interactions
In the title molecule, C17H14BrFN2O, the benzene rings form dihedral angles of 6.58 (6) and 85.31 (6)° with the mean plane of the 4,5-dihydro-1H-pyrazole ring (r.m.s. deviation = 0.0231 Å). The latter ring is planar with a maximum deviation of 0.032 (1) Å The dihedral angle between the benzene rings is 78.75 (6)°. In the crystal, weak C—H⋯O and C—H⋯F hydrogen bonds link the molecules into corrugated layers parallel to the ab plane.
The structure of the title compound, C27H32ClN5O, consists of two crystallographically independent conformers differing slightly in all geometric parameters. Both contain nearly planar purine and benzene ring systems [maximum deviations of 0.046 (3) and 0.005 (2) Å, respectively], the dihedral angles between them being 76.44 (6) and 82.39 (6)°, and an adamantane cage consisting of three fused cyclohexane rings in almost ideal chair conformations, with C—C—C angles in the range 108.7 (2)–110.6 (2)°. The carbonyl plane and the benzene ring are almost coplanar [dihedral angles of 6.43 (9) and 0.64 (8)° in the two conformers]. The crystal structure is stabilized by intermolecular N—H⋯N interactions that link adjacent molecules into dimers and by some non-bonding contacts of the C—H⋯Cl type.
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.
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].
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 title compound, C17H14Cl2N2O, the dihedral angles between the pyrazole ring and the mean planes of the benzene and chloro-substituted benzene rings are 75.97 (1) and 16.63 (1)° respectively. In the crystal, two weak C—H⋯O intermolecular hydrogen bonds and π–π stacking interactions [centroid–centroid distances = 3.774 (4) and 3.716 (7) Å] are observed.
In the title compound, C9H10ClN3O, the semicarbazone group is approximately planar, with an r.m.s. deviation from the mean plane of 0.054 (1) Å. The dihedral angle between the least-squares planes through the semicarbazone group and the benzene ring is 30.46 (5)°. In the solid state, molecules are linked via intermolecular N—H⋯O and N—H⋯N hydrogen bonds, generating R
2(9) ring motifs which, together with R
2(8) ring motifs formed by pairs of intermolecular N—H⋯O hydrogen bonds, lead to the formation of a seldom-observed molecular trimer. Furthermore, N—H⋯O hydrogen bonds form R
1(7) ring motifs with C—H⋯O hydrogen bonds, further consolidating the crystal structure. Molecules are linked by these intermolecular interactions, forming two-dimensional networks parallel to (100).
In the title compound, C16H13ClN4S, the thienopyridine fused-ring system is nearly planar (r.m.s. deviation = 0.0333 Å) and forms a dihedral angle of 4.4 (3)° with the attached dihydroimidazole ring (r.m.s. deviation = 0.0429 Å) allowing for the formation of an intramolecular (exocyclic amine)N—H⋯N(imine) hydrogen bond. The benzene rings of the disordered (50:50) –N(H)—C6H4Cl residue form dihedral angles of 59.1 (3) and 50.59 (15)° with the fused ring system. In the crystal, (imidazole amine)N—H⋯N(pyridine) hydrogen bonds lead to a supramolecular helical chain along the b axis. The chains assemble into layers (ab plane) with inter-digitation of the chlorobenzene rings which results in weak C—H⋯Cl interactions in the c-axis direction.
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.
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, C12H16N2O2, the piperazine ring has a chair conformation. The dihedral angle between the mean planes of the benzene ring and the acetyl group is 48.7 (1)°. In the crystal, molecules are linked via O—H⋯O hydrogen bonds, forming chains propagating along .
The title compound, C18H14Cl2N2O2, crystallizes with two molecules, A and B, in the asymmetric unit. In molecule A, the dihedral angles between the central pyrazole ring and pendant dichlorobenzene and p-tolyl rings are 2.18 (16) and 46.78 (16)°, respectively. In molecule B, the equivalent angles are 27.45 (16) and 40.45 (18)°, respectively. Each molecule features an intramolecular O—H⋯O hydrogen bond, which closes an S(6) ring and molecule A also features a C—H⋯O interaction. In the crystal, weak C—H⋯π interactions and aromatic π–π stacking [shortest centroid–centroid separation = 3.707 (2) Å] generate a three-dimensional network.
crystal structure; Schiff-base pyrazole derivative; hydrogen bonding; C—H⋯π interactions; aromatic π–π stacking