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, C17H15ClN2O2, the benzene rings form dihedral angles of 89.56 (5) and 5.87 (5)° with the mean plane of the pyrazoline ring (r.m.s. deviation = 0.084 Å). The dihedral angle between the two benzene rings is 87.57 (5)°. In the crystal, molecules are linked by O—H⋯O and C—H⋯O hydrogen bonds into a helical chain along the c axis. Between the chains weak C—H⋯N and C—H⋯O interactions are present. The crystal studied was an inversion twin with a domain ratio of 0.72 (4):0.28 (4).
The asymmetric unit of the title compound, C26H25ClN2O3, contains two independent molecules (A and B). The conformation of the two molecules differs essentially in the dihedral angle involving the two benzene rings. They are inclined to one another by 52.47 (10) in A and by 31.75 (11)° in B. In both molecules, the six-membered piperidin-3-one rings have chair conformations. In molecule A, all four five-membered rings have twist conformations. In molecule B, only three of the four five-membered rings have twist conformations. The fourth, of the inden-1-one moiety, has an envelope conformation with the spiro C atom, bonded to the N atom of the pyrrolidine ring, as the flap. A weak intramolecular O—H⋯N hydrogen bond occurs in each independent molecule while a C—H⋯O interaction is also observed in molecule A. In the crystal, pairs of O—H⋯O hydrogen bonds link the molecules, forming inversion dimers with graph-set motif R
2(12). These dimers are further interconnected by C—H⋯O and C—H⋯π interactions, forming a three-dimensional network.
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, C22H24ClN3O4, intramolecular C—H⋯O and C—H⋯N hydrogen bonds form S(9) and S(7) ring motifs, respectively. The 1,4-dihydropyridine ring adopts a flattened boat conformation. The benzene ring makes a dihedral angle of 33.36 (6)° with the pyrazole ring. In the crystal, pairs of N—H⋯N hydrogen bonds link the molecules into inversion dimers. The dimers are stacked in column along the a axis through N—H⋯O and C—H⋯N hydrogen bonds. The crystal packing also features C—H⋯π interactions involving the pyrazole ring.
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, 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 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 R
2(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 .
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.
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 molecule, C11H10ClN5OS, an intramolecular N—H⋯O hydrogen forms an S(6) ring motif. The dihedral angle between the pyrazole ring and the benzene ring is 3.77 (8)°. In the crystal, molecules are linked by N—H⋯S and N—H⋯O hydrogen bonds into layers parallel to the bc plane.
The title compound, C32H23ClN2O4, has a quinoline, a chlorophenyl and an acenaphthalene ring system attached to a central pyrrolidine ring, which has three stereogenic centers. Nevertheless, the compound crystallizes as a racemate with two molecules of identical chirality in the asymmetric unit. They differ in the conformation of the five-membered pyrrolidine ring; in one molecule it has an envelope conformation, while in the other molecule it has a twisted conformation. In each molecule there is an intramolecular O—H⋯O hydrogen bond making an S(6) ring motif. In the crystal, pairs of N—H⋯O hydrogen bonds produce inversion dimers with R
2(8) motifs. There are also C—H⋯O interactions present. The crystal structure contains voids (60 Å3) within which there is no evidence of solvent molecules.
In the title compound, C24H17ClFN3S, the pyrazole ring is almost planar (r.m.s. deviation = 0.030 Å). With the exception of the methine-bound benzene ring, which forms a dihedral angle of 85.77 (13)° with the pyrazole ring, the remaining non-C atoms lie in an approximate plane (r.m.s. deviation = 0.084 Å) so that overall the molecule has a T-shape. In the crystal, centrosymmetrically related molecules are connected via π–π interactions between pyrazole rings [centroid–centroid distance = 3.5370 (15) Å] and these stack along the a axis with no specific interactions between them.
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.
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 synthesis of 3-[5-(4-chlorophenyl)-1-(4-methoxyphenyl)-1H-pyrazol-3-yl]propionic acid, C19H17ClN2O3, (I), and its corresponding methyl ester, methyl 3-[5-(4-chlorophenyl)-1-(4-methoxyphenyl)-1H-pyrazol-3-yl]propionate, C20H19ClN2O3, (II), is regiospecific. However, correct identification of the regioisomer formed by spectroscopic techniques is not trivial and single-crystal X-ray analysis provided the only means of unambiguous structure determination. Compound (I) crystallizes with Z′ = 2. The propionic acid groups of the two crystallographically unique molecules form a hydrogen-bonded dimer, as is typical of carboxylic acid groups in the solid state. Conformational differences between the methoxybenzene and pyrazole rings give rise to two unique molecules. The structure of (II) features just one molecule in the asymmetric unit and the crystal packing makes greater use than (I) of weak C—H⋯A interactions, despite the lack of any functional groups for classical hydrogen bonding.
The asymmetric unit of the title compound, C25H14ClFN4S, contains two independent molecules (A and B). Each molecule consists of five rings, namely chlorophenyl, fluorophenyl, 1H-pyrazole, thiazole and benzonitrile. In molecule A, the 1H-pyrazole ring makes dihedral angles of 52.54 (8), 35.96 (8) and 15.43 (8)° with respect to the attached chlorophenyl, fluorophenyl and thiazole rings. The corresponding values in molecule B are 51.65 (8), 37.26 (8) and 8.32 (8)°. In the crystal, molecules are linked into dimers by C—H⋯N hydrogen bonds, generating R
2(10) ring motifs. These dimers are further linked into two-dimensional arrays parallel to the ab plane via intermolecular weak C—H⋯N and C—H⋯F hydrogen bonds. The crystal structure is further stabilized by weak π-π interactions [with centroid–centroid distances of 3.4303 (9) and 3.6826 (9) Å] and weak C—H⋯π interactions.
The title compound is a 1,4-diaroyl pyrazole derivative and has three aromatic rings. In the crystal, molecules are linked through stacking interactions between the pyrazole rings and between the naphthalene and phenyl rings, and through intermolecular C—H⋯O hydrogen bonds to form inversion dimers.
The title compound, C21H12Cl2N2O3, is a 1,4-diaroyl pyrazole derivative and has three aromatic rings. The dihedral angles between the naphthalene ring system and the pyrazole ring, the pyrazole and phenyl rings and the naphthalene ring system and the phenyl ring are 49.44 (13), 49.87 (16) and 0.58 (11)°, respectively. The phenolic proton forms an intramolecular O—H⋯O hydrogen bond with an adjacent carbonyl O atom. In the crystal, the molecules are linked through stacking interactions between the pyrazole rings [centroid–centroid distances = 3.546 (3)] and between the naphthalene ring system and the phenyl ring [centroid–centroid distances = 3.609 (4) Å] along the a-axis direction. The molecules are further connected through C—H⋯O hydrogen bonds, forming inversion dimers.
crystal structure; diaroyl pyrazole; cyclization; stacking interaction; C—H⋯O hydrogen bonding
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 R
2(16) graph-set motif. C—H⋯π interactions link the dimers into columns propagating in .
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 compound, C28H21ClN2O3, the quinoline ring system is essentially planar with a maximum deviation of 0.0436 (17) Å. The isoxazole and cyclohexane rings adopt envelope conformations. The isoxazole ring is almost orthogonal to both the quinoline ring system and the cyclohexane ring, making dihedral angles of 85.75 (8) and 81.46 (9) °, respectively. The O atom deviates signifigantly from the six-membered carbocyclic ring by 0.3947 (16) Å. In the crystal, molecules are linked into inversion dimers via pairs of C—H⋯O interactions, resulting in R
2(24) ring motifs.
In the title molecule, C24H21ClN4OS, the 1,2,4-triazole ring forms dihedral angles of 37.2 (2), 71.9 (2) and 84.9 (2) ° with the three benzene rings. In the crystal, weak intermolecular N—H⋯S hydrogen bonds link the molecules into centrosymmetric dimers.
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
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.
The title compound, C19H15Cl2N3O2, was obtained by a one-step cyclocondensation of 2-amino-1-(4-chlorophenyl)imidazoline with diethyl (2-chlorobenzyl)malonate under basic conditions. In the crystalline state, the molecule exists as the 7-hydroxy-5-oxo tautomer. The dihedral angles between the fused imidazopyrimidine and aromatic chlorophenyl and chlorobenzyl rings are 14.2 (1) and 70.7 (1)°, respectively. The conformation of the molecule is influenced by the intramolecular C—H⋯O and C—H⋯N hydrogen bonds, giving a nearly planar five-ring fused system [maximum deviation from the mean plane = 0.296 (2) Å]. In the crystal structure, strong intermolecular O—H⋯O hydrogen bonds link the molecules into chains along the c axis. These chains are further stabilized by weak C—H⋯Cl and π–π interactions [centroid–centroid distance = 3.6707 (12) Å].