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 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.
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.
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).
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, 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 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 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, C11H10O3, there is an intramolecular O—H⋯O hydrogen bond generating an S(6) ring motif. The O atom of the hydroxy group deviates by 0.0200 (1) Å from the benzene ring to which it is attached. The propyne group is almost linear, the C—C C angle being 177.83 (15)°, and is almost coplanar with the benzene ring; the C—C—O—C torsion angle being only −1.1 (2)°. In the crystal, molecules are linked via C—H⋯O hydrogen bonds, forming infinite C(11) chains running parallel to . These chains are linked by a pair of C—H⋯O hydrogen bonds, enclosing R
2(8) inversion dimers, forming a corrugated two-dimensional network lying parallel to (103).
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.
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 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 title compound, C18H22N2O3, represents a (4S,5R,6S)-stereoisomer, crystallizing as a racemate in a centrosymmetric space group. The six-membered aliphatic ring adopts a half-chair conformation, with the hydroxy- and acetyl-substituted C atoms deviating by 0.458 (2) and −0.366 (2) Å, respectively, from the plane defined by other four ring atoms. The pyrazole ring is essentially planar [r.m.s deviation = 0.004 (2) Å]. In the crystal, the molecules are linked into chains along the b axis by N—H⋯N hydrogen bonds. The chains are linked by O—H⋯N hydrogen bonds into layers parallel to the bc plane.
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, 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 molecule, C20H19N3O4S, the heterocyclic thiazine ring adopts a half-chair conformation with the S and N atoms displaced by 0.492 (6) and 0.199 (6) Å, respectively, on opposite sides from the mean plane formed by the remaining ring atoms. The ethanone group lies at an angle of 9.4 (2)° with respect to the benzene ring, which lies almost perpendicular to the pyrazole ring, with a dihedral between the two planes of 78.07 (9)°. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds.
In the title compound, C19H17Cl2N3O2, there are three molecules (A, B and C) in the asymmetric unit and each differs in the conformation adopted. As a result of steric repulsion, the amide group is rotated with respect to both the dichlorophenyl and 2,3-dihydro-1H-pyrazol-4-yl rings, making dihedral angles of 44.5 (2) and 56.2 (2)°, respectively in A, 51.1 (2) and 54.1 (2)° in B, and 53.8 (2) and 54.6 (2)° in C. The dihedral angles between the dichlorophenyl and 2,3-dihydro-1H-pyrazol-4-yl rings are 54.8 (2), 76.2 (2) and 77.5 (2)° in molecules A, B and C, respectively, while the 2,3-dihydro-1H-pyrazol-4-yl and phenyl rings make dihedral angles of 45.3 (2), 51.2 (2) and 42.8 (2)°, respectively. In the crystal, two of the molecules are linked through N—H⋯O hydrogen bonding to an adjoining molecule, forming dimers of the R
2(10) type, while the third molecule forms such dimers with itself. C—H⋯O interactions link the dimers.
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, C15H17NO3, the mean planes of the pyrrole and benzene rings form a dihedral angle of 81.92 (7)°. The molecule contains an intramolecular O—H⋯O hydrogen bond. In the crystal, weak C—H⋯π interactions link the molecules into chains along .
The title co-crystal, 3-(4-fluorophenyl)-1H-pyrazole–5-(4-fluorophenyl)-1H-pyrazole (1/1), C9H7FN2, crystallizes with four independent molecules (A, B, C and D) in the asymmetric unit exhibiting two tautomeric forms (A and D; B and C) due to N—H proton exchange between the two N atoms of the pyrazole ring. The dihedral angles between the mean planes of the pyrazole and benzene rings are 15.6 (1), 19.8 (9), 14.0 (1) and 10.7 (7)° in molecules A, B, C and D, respectively. In the crystal, N—H⋯N hydrogen bonds link the four molecules in the asymmetric unit into a ring with an R
4(12) motif. Furthermore, weak C—H⋯F interactions link the molecules into a three-dimensional network.
crystal structure; pyrazole derivative; tautomeric forms; hydrogen bonds
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].
The asymmetric unit of the title compound, C23H18N2O3S, contains two molecules with comparable geometries. In one molecule, the pyrazole ring forms dihedral angles of 61.65 (11), 47.88 (11) and 63.20 (14)° with the three benzene rings. The corresponding values for the other molecule are 77.19 (11), 43.55 (11) and 63.56 (15)°. In the crystal, both molecules are linked into inversion dimers by pairs of C—H⋯S hydrogen bonds, generating R
2(14) loops in each case.
In the title compound, C17H18N2O3, the benzene rings form a dihedral angle of 3.34 (2)°. There is a strong intramolecular O—H⋯N hydrogen bonds (which induces planarity of the structure). In the crystal, molecules are linked by pairs of O—H⋯N hydrogen bonds, forming inversion 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
The asymmetric unit of the title compound, 2C13H14N2O3·C3H10NO3
+·Cl−, contains two independent molecules (A and B) of the title pyrimidine derivative and one ion-pair of tris(hydroxymethyl)ammonium chloride. The pyrimidine ring in each pyrimidine derivative has a half-chair conformation. Its mean plane is inclined to the benzene ring by 87.2 (3)° in molecule A and 85.7 (2)° in molecule B. In the crystal, the pyrimidine derivatives are connected to each other by N—H⋯O hydrogen bonds, forming chains propagating along the b-axis direction. The chains are linked via O—H—Cl hydrogen bonds, forming corrugated sheets lying parallel to the bc plane. The sheets are linked via C—H⋯O hydrogen bonds, forming a three-dimensional framework. The tris(hydroxymethyl)ammonium chloride molecules are located in the cages of the framework. There are also further C—H⋯O hydrogen bonds and C—H⋯π interactions present in the three-dimensional framework structure. Both the cation and chloride anion of the tris(hydroxymethyl)ammonium chloride ion pair are disordered over two positions, with a refined occupancy ratio of 0.418 (8):0.582 (8) for the cation and 0.71 (4):0.29 (4) for the anion.