There are two independent molecules in the asymmetric unit of the title compound, C12H9ClN2OS, a Schiff base derived from hydrazide, in which the dihedral angles between the thiophene and benzene rings are 3.6 (3) and 7.3 (3)°. In the crystal, the two independent molecules are arranged about an approximate non-crystallographic inversion center and are connected by two N—H⋯O hydrogen bonds. Weak C—H⋯Cl contacts are also present. Conversely, there are neither significant aromatic stacking interactions nor contacts involving S atoms.
The title compound, C16H11ClN2O2·H2O, exists in an E conformation with respect to the N=C bond. The benzofuran ring system forms a dihedral angle of 1.26 (4)° with the benzene ring. In the crystal, molecules are linked via (N,C)—H⋯O bifurcated acceptor hydrogen bonds and (O,O,C)—H⋯O trifurcated acceptor hydrogen bonds, forming layers parallel to the bc plane.
In the Schiff base molecule of the title compound, C20H14ClN3O3·CH3COOH·H2O, the central benzene ring makes dihedral angles of 36.26 (7) and 27.59 (8)°, respectively, with the terminal chlorophenyl and pyridine rings. In the crystal, the three components are linked by O—H⋯O, N—H⋯O, O—H⋯N and C—H⋯O hydrogen bonds into a double-tape structure along the a axis.
The title arylsulfonyl glycinyl hydrazone Schiff base compound crystallizes as a monohydrate. In the crystal, a series of O—H⋯O and N—H⋯O hydrogen bonds leads to the formation of corrugated sheets lying parallel to (100).
The molecule of the title compound, C16H16ClN3O3S·H2O, is L-shaped being bent at the S atom; the S—N—C—C torsion angle is 132.0 (3)°. The central part of the molecule, C—C—N—N=C, is almost linear, with the C—C—N—N and C—N—N=C torsion angles being −174.1 (2) and 176.0 (2)°, respectively. The dihedral angle between the p-toluenesulfonyl ring and the S—N—C—C(=O) segment is 67.5 (4)°, while that between the two aromatic rings is 52.17 (11)°. In the crystal, the water H atom is involved in O—H⋯O hydrogen bonds with a sulfonamide O atom and the carbonyl O atom. The water O atom is itself hydrogen bonded to both NH hydrogen atoms. These four hydrogen bonds lead to the formation of corrugated sheets lying parallel to (100). There are also weak C—H⋯O contacts present within the sheets.
crystal structure; synthesis; arylsulfonyl glycinyl hydrazone; hydrogen bonding
In the title compound, C14H12ClN3O2·H2O, the benzene ring and the pyridine rings are oriented at a dihedral angle of 57.73 (12)° and an intramolecular O—H⋯N hydrogen bond generates an S(6) ring. In the crystal, the water molecule forms O—H⋯O and O—H⋯N hydrogen bonds to the organic molecule, leading to chains containing R
4(16) loops. In addition, weak aromatic π–π stacking interactions between the centroids of pyridine rings [at distance of 3.864 (2) and 4.013 (2) Å] and C—H⋯π interactions occur.
The crystal of the title Schiff base compound, C20H18ClN3O3·H2O, was twinned by a twofold rotation about (100). The asymmetric unit contains two crystallographically independent molecules with similar conformations, and two water molecules. The C=N—N angles of 115.7 (6) and 116.2 (6)° are significantly smaller than the ideal value of 120° expected for sp
2-hybridized N atoms and the dihedral angles between the benzene ring and quinoline ring system in the two molecules are 52.5 (7) and 53.9 (7)°. The molecules aggregate via C—Cl⋯π and π–π interactions [centroid–centroid distances = 3.696 (5)–3.892 (5) Å] and weak C—H⋯O interactions as parallel sheets, which are further linked by water molecules through N—H⋯O and O—H⋯O hydrogen bonds into a supramolecular two-dimensional network.
Single crystals of the title compound, C16H14N2O5·H2O, were obtained from a condensation reaction of 1,3-benzodioxole-5-carbohydrazide and 3-methoxysalicylaldehyde in a 95% ethanol solution. The asymmetric unit consists of a Schiff base molecule, which assumes an E configuration with respect to the C=N bond, and a water molecule of crystallization. The dihedral angle between the two substituted benzene rings is 12.7 (2)°. In the crystal structure, molecules are linked through intermolecular N—H⋯O and O—H⋯O hydrogen bonds, forming layers parallel to the bc plane.
In the asymmetric unit of the title compound, C19H27ClN4O·0.5C2H6O·1.5H2O, there are two molecules of the Schiff base, which has a rigid adamantyl cage at one end of the C(= O)NH–N=CH– chain and an almost planar [torsion angles = 1.3 (1) and 7.9 (2)° imidazolyl ring at the other end, three molecules of water and one molecule of ethanol. In both independent molecules of the Schiff base, this chain displays an extended zigzag configuration. All their amino groups function as hydrogen-bond donors to water molecules; these are linked to other acceptor atoms, generating a layer structure. O—H⋯O and O—H⋯N interactions involving the water molecules also occur.
In the title compound, C13H11ClN4O3, the phenyl and pyrrolyl ring are linked by an acyl–hydrazone (R
2C=N—N—CO—R) group, forming a slightly bent molecule: the dihedral angle subtended by the the phenyl and pyrrolyl rings is 8.46 (12)°. In the crystal, the three-dimensional supramolecular structure is assembled by N—H⋯O hydrogen bonding. Molecular sheets are formed parallel to (101) in a herringbone arrangement by weak van der Waals interactions; weak π–π [centroid–centroid phenyl–phenyl and pyrrolyl–pyrrolyl distances of 3.7816 (3) and 3.8946 (2) Å, respectively] interactions occur between neighbouring sheets.
In the title compound, C13H12ClN3·H2O, the organic molecule is almost planar, with a dihedral angle of 3.22 (10)° between the benzene and pyridine rings. The crystal structure is stabilized by O—H⋯N and C—H⋯O hydrogen bonding and π–π stacking interactions [centroid–centroid distances = 3.630 (1) and 3.701 (1) Å].
The asymmetric unit of the title compound, C14H13ClN2O2S·0.15H2O, a novel sulfonamide derivative, comprises two crystallographically independent molecules (A and B) and a water molecule of crystallization, which is partially occupied. One of the molecules (B) is disordered over two positions (B and C) with refined site occupancies of 0.605 (10) and 0.395 (10). The dihedral angles between the two benzene rings in molecules A, B and C are 67.8 (3), 74.6 (5) and 84.96 (11)°, respectively. In the crystal structure, intermolecular N—H⋯O and C—H⋯O hydrogen bonds link the components of the asymmetric unit. The crystal structure is further stabilized by intermolecular π–π interactions [centroid–centroid distances = 3.4518 (10)–3.5859 (10) Å].
The conformation about each of the imine and ethene bonds in the title hydrazide hydrate, C16H13ClN2O·H2O, is E. The hydrazide molecule is approximately planar (r.m.s. deviation of the 20 non-H atoms = 0.172 Å). The most significant twist occurs about the ethene bond [C—C=C—C = 164.1 (5)°] and the dihedral angle formed between the benzene rings is 5.3 (2)°]. In the crystal, the presence of N—H⋯Ow and O—H⋯Oc (× 2; w = water and c = carbonyl) hydrogen bonds leads to a supramolecular array in the bc plane.
The planar pyrazolidine ring occurs in the betaine form with a Z conformation of the exocyclic C=N bond. In the crystal, C—H⋯O and C—H⋯π interactions result in the formation of ribbons of molecules along .
The title molecule, C17H15ClN2O2, is L-shaped with the 4-chlorobenzylidene ring almost coplanar with the planar pyrazolidine ring (r.m.s. deviation = 0.020 Å), making a dihedral angle of 4.83 (17)°. The 4-methoxyphenyl ring is almost normal to the mean plane of the pyrazolidine ring and the 4-chlorobenzylidene ring, with dihedral angles of 87.36 (17) and 89.23 (16)°, respectively. The pyrazolidine ring occurs in the betaine form with a Z configuration for the exocyclic C=N bond. In the crystal, C—H⋯O and C—H⋯π interactions generate ribbons of molecules along [1-10].
crystal structure; pyrazolidinium ylide; betaine structure
The asymmetric unit of the title compound, C20H16ClN3S, contains two independent molecules, A and B. In molecule A, the dihedral angles between the central benzene ring and the pendant chlorobenzene and phenyl rings are 6.37 (15) and 64.79 (15)°, respectively. The corresponding values in molecule B are 28.21 (14) and 82.11 (16)°, respectively. Each molecule features an intramolecular N—H⋯N hydrogen bond, which generates an S(5) ring. In the crystal, molecules A and B form dimers, being linked by two N—H⋯S hydrogen bonds with graph-set notation R
The organic molecule of the title monohydrate, C12H9IN2O3·H2O, features a disordered furyl ring with the major component [site occupancy = 0.575 (18)] having the carbonyl O and furyl O atoms syn, and the other conformation having these atoms anti. The molecule is slightly twisted with the dihedral angle between the benzene and furyl rings being 10.3 (6)° (major component). An intramolecular O—H⋯N(imine) hydrogen bond is formed. In the crystal, the water molecule accepts a hydrogen bond from an amine H atom, and forms two O—H⋯O(carbonyl) hydrogen bonds, thereby linking three different carbohydrazide molecules. The result is a supramolecular layer parallel to (001). The closest contacts between layers are of the type I⋯I, at a distance of 3.6986 (6) Å.
The title compound, C12H10N4O2·H2O, was synthesized by the reaction of pyrazine-2-carboxylic acid hydrazide and 3-hydroxybenzaldehyde in ethanol. In the crystal structure, the organic molecules are linked into extended chains by intermolecular N(amide)—H⋯O(hydroxy) hydrogen bonds. Additional hydrogen bonds between the water molecule and three adjacent organic molecules, as well as face-to-face π–π stacking interactions between the benzene and pyrazine rings [centroid-to-centroid separation = 3.669 (2) Å and offset = 1.362 Å], link the molecules into a three-dimensional framework.
The asymmetric unit of the title compound, C16H12ClN3S, contains two independent molecules whose conformations differ primarily in the orientations of the phenyl and chlorobenzene rings with respect to the thiazole ring. In the first molecule, the dihedral angles are 3.0 (1) and 9.2 (1)°, respectively, for the phenyl ring and the chlorobenzene ring, while in the second molecule, the corresponding angles are 18.6 (1) and 23.4 (1)°. In the crystal, the two independent molecules are associated via complementary N—H⋯N hydrogen bonds into a dimer. These dimers are associated through weak C—H⋯Cl and C—H⋯S interactions into supramolecular chains propagating along the a-axis direction.
crystal structure; 1,3-thiazole; hydrogen bonding; hydrogen-bonded dimers
The asymmetric unit of the title compound, 2C15H9F6N3O·H2O, contains two independent Schiff base molecules and one water molecule. Both Schiff base molecules exist in an E configuration with respect to the C=N double bonds and the dihedral angles between the benzene and the pyridine rings in the two molecules are 17.53 (12) and 20.62 (12)°. In the crystal structure, molecules are linked by intermolecular N—H⋯O and C—H⋯O hydrogen bonds into infinite one-dimensional chains along the a axis. In addition, intermolecular O—H⋯N, O—H⋯F, C—H⋯F and C—H⋯O hydrogen bonds further link these chains into a three-dimensional network. Weak π–π interactions with centroid–centroid distances in the range 3.6495 (17)–3.7092 (16) Å are also observed.
The asymmetric unit of the title compound, C14H11ClN2O, contains two independent molecules. In one molecule, the two aromatic rings form a dihedral angle of 45.94 (16)°, while in the second molecule this angle is 58.48 (16)°. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules into two crystallographically independent sets of chains propagating along .
In the crystal structure of the title compound, 2C10H7NO4·C14H13N3O2, the two independent acid molecules are connected through strong O—H⋯N and O—H⋯O hydrogen bonds to the central molecule of the antitubercular drug N′-[(E)-4-methoxybenzylidene]pyridine-4-carbohydrazide. Two such trimolecular units related by an inversion centre interact through a pair of N—H⋯O hydrogen bonds, forming a 3 + 3 molecular aggregate. The dihedral angle between the aromatic rings of the hydrazone molecule is 1.99 (12)°. The crystal packing features weak C—H⋯O and π–π stacking interactions, with centroid–centroid distances of 3.8460 (19) and 3.8703 (13) Å.
In the title compound, C12H11N3O3·2H2O, the dihedral angle formed by the planes of the pyridine and the furan rings of the organic carbohydrazide molecule is 4.66 (7)°. In the crystal, these molecules form stacks along the b-axis direction, neighbouring molecules within each stack being related by inversion and the shortest distance between the centroids of the pyridine and furan rings being 3.714 (1) Å. Molecules from neighboring stacks are linked by pairs of N—H⋯O hydrogen bonds. The water molecules fill the channels between the stacks being linked by O—H⋯O hydrogen bonds into helices along . Besides this, water molecules are involved in O—H⋯N and O—H⋯O hydrogen bonds with the carbohydrazide molecules, thus forming a three-dimensional network, augmented by weak C—H⋯O interactions.
In the title compound, C12H9ClN2O2·H2O, the dihedral angle between the aromatic rings is 13.9 (2)° and an intramolecular N—H⋯O hydrogen bond occurs. In the crystal structure, the components are linked by N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds.
The title compound, C14H10ClN3O4·CH4O, was synthesized from the reaction of 5-chlorosalicylaldehyde with 4-nitrobenzohydrazide in methanol. The Schiff base molecule is nearly planar, with a dihedral angle of 9.1 (3)° between the two benzene rings. The methanol solvent molecules are linked to the Schiff base molecules by N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds, forming chains running parallel to the a axis.
In the Schiff base molecule of the title compound, C14H11ClN2O3·2H2O, the benzene rings form a dihedral angle of 20.6 (1)°. The water molecules of crystallization are involved in the formation of a three-dimensional hydrogen-bonding network via O—H⋯O and N—H⋯O hydrogen bonds.
In the title compound, C13H9ClN4O4, there are two crystallographically independent molecules in the asymmetric unit, which have very similar conformations. The C=N—N angles in each independent molecule are 115.0 (2) and 116.6 (2)°, which are significantly smaller than the ideal value of 120° expected for sp
2-hybridized N atoms. This is probably a consequence of repulsion between the nitrogen lone pairs and the adjacent N—N bonds. Two bifurcated intramolecular N—H⋯O hydrogen bonds help to establish the molecular conformation and consolidate the crystal packing.