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].
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, C22H18O3, an intramolecular O—H⋯O hydrogen bond stabilizes the molecular structure, forming an S(6) ring motif. The central benzene ring forms a dihedral angle of 64.74 (5)° with the phenyl ring and a dihedral angle of 5.58 (5)° with the terminal benzene ring. In the crystal, molecules are linked into columns along the a axis via intermolecular C—H⋯O hydrogen bonds. C—H⋯π interactions involving the centroid of the hydroxy-substituted benzene ring further stabilize the crystal structure.
The title benzophenone compound, C14H12O6·H2O, was isolated from the bark of Garcinia hombroniana Pierre (Guttiferae). The molecule is twisted, the dihedral angle between the two benzene rings being 59.13 (7)°. The methoxy group is approximately coplanar with the attached benzene ring, with a C—O—C—C torsion angle of 1.91 (18)°. The water molecule is disordered over two positions in a 0.555 (19):0.445 (19) ratio. An intramolecular O—H⋯O hydrogen bond generates an S(6) ring motif. The crystal structure is stabilized by intermolecular O—H⋯O hydrogen bonds. These interactions link the molecules into sheets parallel to the ac plane. The sheets are stacked along the b axis by π–π interactions, with centroid–centroid distances of 3.6219 (7) Å. A weak O—H⋯π interaction was also noted.
In the title compound, C13H11ClO2, the dihedral angle between the mean planes of the 2-chlorophenyl and phenol rings is 87.4 (9)°. The methyl hydroxy group lies nearly perpendicular to the plane of its attached benzene ring [O—C—C—C torsion angle = 84.3 (3)°]. The two hydroxy groups lie on the same side of the molecule and are in a slightly twisted gauche conformation [O—C—C—O torsion angle = 77.1 (8)°] to each other. In the crystal, O—H⋯O hydrogen bonds between nearby methylhydroxy groups form dimers in alternating pairs aligned diagonally along the b axis. A view along the c axis reveals a hexameric aggregate mediated by a ring of six O—H⋯O hydrogen bonds generating an R
6(12) motif loop.
The title compound, C25H34N2O5, was synthesized from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-12-methylen-3, 14-dioxa-tricyclo[9.3.0.02,4]tetradec-7-en-13-one), which in turn was isolated from the chloroform extract of the aerial parts of Anvillea radiata. The molecule comprises a ten-membered ring fused to a five-membered ring with an additional epoxy ring system fused to the ten-membered ring. The five-membered ring also carries a 4-hydroxyphenyl-piperazin-1-ylmethyl substituent. The ten-membered ring adopts an approximate chair–chair conformation, while the piperazine ring displays a chair conformation and the five-membered ring shows an envelope conformation with the C atom closest to the hydroxy group forming the flap. Two C atoms in the phenyl ring and the O atom of the hydroxyl group are disordered over two sites, with an occupancy ratio of 0.53 (5):0.47 (5). An intramolecular O—H⋯N hydrogen-bond stabilizes the molecular conformation. In the crystal, C—H⋯O hydrogen bonds link the molecules into zigzag chains running along the a-axis direction.
In the title molecule, C24H18ClNO6S, the heterocyclic thiazine ring adopts a half chair conformation with the S and N atoms displaced by 0.318 (3) and 0.387 (3) Å, respectively, on the opposite sides from the mean plane formed by the remaining ring atoms. The benzene rings of the benzothiazin unit and methoxybenzoyl group are more or less coplanar, the dihedral angle between the mean planes of these rings being 12.37 (10)° while the chlorophenyl ring is inclined at 81.87 (4) and 73.30 (5)°, respectively, to these rings. The molecular structure is consolidated by intramolecular O—H⋯O and C—H⋯N interactions and the crystal packing is stabilized by weak intermolecular C—H⋯O hydrogen bonds.
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, C17H16O3, the carbonyl group is in an s-cis configuration with respect to the olefinic double bond. The dihedral angle between the two benzene rings is 2.85 (3)°. The prop-2-en-1-one bridge makes dihedral angles of 4.77 (4) and 4.15 (4)°, respectively, with the 2-hydroxyphenyl and 4-ethoxyphenyl rings. The ethoxy group is coplanar with the attached phenyl ring [Car—O—C—C = 179.72 (5)°]. An intramolecular O—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal structure, molecules are stacked in an antiparallel manner to form columns along the b axis. The columnar structure is stabilized by C—H⋯π interactions involving the 2-hydroxyphenyl ring.
The title Schiff base compound, C14H10ClNO4, has been synthesized by the reaction of 5-amino-2-hydroxybenzoic acid and 5-chloro-2-hydroxybenzaldehyde. The molecule is a zwitterion in the crystal, with the phenolic hydroxy group deprotonated and the imine N atom protonated. It adopts an E configuration about the central C=N double bond. The dihedral angle between the two benzene rings is 3.83 (7)°. Intramolecular N—H⋯O and O—H⋯O hydrogen bonding generates S(6) ring motifs. In the crystal, molecules are connected by intermolecular O—H⋯O and C—H⋯Cl hydrogen bonds, forming a supramolecular chain.
The title Schiff base compound, C20H14ClNO2, adopts an E configuration about the azomethine bond. The phenol and chlorobenzene rings form dihedral angles of 84.71 (9) and 80.70 (8)°, respectively, with the phenyl ring and are twisted by 15.32 (8)° with respect to one another. The molecular conformation is stabilized by an intramolecular O—H⋯N hydrogen bond, which forms an S(6) ring motif. In the crystal, molecules are linked by C—H⋯O hydrogen bonds, forming columns parallel to the a axis.
In the title compound, C21H21BrClNO4, the dihydropyridine ring adopts a flattened boat conformation. The 3-bromo-5-chloro-2-hydroxyphenyl ring forms a dihedral angles of 84.44 (7)° with the dihydropyridine mean plane. The molecular conformation is stabilized by an intramolecular O—H⋯O hydrogen bond, with an S(8) ring motif. In the crystal, O—H⋯O and C—H⋯O hydrogen bonds link the molecules, forming a three-dimensional network.
Crystal structure of 9-(3-bromo-5-chloro-2-hydroxyphenyl)-10-(2-hydroxyethyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione
The structure of a hydroacridine with significant pharmaceutical potential is reported. The acridinone ring system is in the shape of a shallow V with the majority of the ring system substituents on its convex surface; a plethora of classical and non-classical hydrogen bonds stack the molecules into interconnected columns.
The title compound C25H29BrClNO4, comprises a 3,3,6,6-tetramethyltetrahydroacridine-1,8-dione ring system that carries a hydroxyethyl substituent on the acridine N atom and a 3-bromo-5-chloro-2-hydroxyphenyl ring on the central methine C atom of the dihydropyridine ring. The benzene ring is inclined to the acridine ring system at an angle of 89.84 (6)° and this conformation is stabilized by an intramolecular O—H⋯O hydrogen bond between the hydroxy substituent on the benzene ring and one of the carbonyl groups of the acridinedione unit. In the crystal, O—H⋯O, C—H⋯O and C—H⋯Br hydrogen bonds combine to stack molecules in interconnected columns propagating along the a-axis direction.
crystal structure; acridine; hydroacridine
In the title compound, C20H21NO4, the two benzene rings are almost perpendicular to each other, making a dihedral angle of 86.1 (7)°. The hydroxyethanimine group is essentially coplanar with the benzene ring, the largest deviation from the mean plane of the hydroxyethanimine [C=N—OH] group being 0.011 (1) Å for the O atom. An intramolecular C—H⋯O hydrogen bond occurs. The molecules are linked into cyclic centrosymmetric R
2(6) dimers via O—H⋯N hydrogen bonds. Intermolecular C—H⋯O hydrogen bonds link the molecules, forming a C(8) chain along the a axis. The crystal packing is further stabilized by C—H⋯π interactions.
The title compound, C13H11NO3, crystallizes in a zwitterionic form and has a trans configuration about the C=N bond. The molecule is almost planar, the dihedral angle between the two benzene rings being 4.32 (8)°. The two hydroxy substituents are coplanar with each of their attached benzene rings [r.m.s. deviations of 0.0053 (2) and 0.0052 (2) Å]. An intramolecular N—H⋯O hydrogen bond formed between the iminium N and the phenolate O atom generates an S(6) ring motif. In the crystal, the molecules are linked through O—H⋯O hydrogen bonds into chains along . Two neighbouring chains are further connected through O—H⋯O hydrogen bonds in an antiparallel manner. π–π interactions are also observed, with centroid–centroid distances of 3.7115 (19) and 3.743 (2) Å.
The title compound, C13H12N4O2, crystallized with two independent molecules (A and B) in the asymmetric unit. Molecule B is planar to within 0.044 (3) Å for all non-H atoms, while molecule A is slightly twisted, with a dihedral angle of 6.29 (4)° between the mean planes of the pyrazine-2-carbohydrazide and 1-(2-hydroxyphenyl)ethanone moieties (r.m.s. deviations = 0.0348 and 0.0428 Å, respectively). S(5) and S(6) ring motifs are formed in both molecules due to the presence of intramolecular O—H⋯N and N—H⋯N hydrogen bonds. In the crystal, molecules A and B are linked by a C—H⋯O hydrogen bond. They stack along the a-axis direction, forming columns with π–π interactions involving inversion-related pyrazine and benzene rings [centroid–centroid distances = 3.5489 (13)–3.8513 (16) Å].
The title compound, C18H16O8, was isolated from the plant Artemisia baldshuanica Krasch et Zarp. The molecule is approximately planar, with the exception of the terminal methyl groups, the C atoms of which devitate from their attached ring planes by 1.243 (5) and 1.168 (5) Å. The dihedral angle between the substituted benzopyran and benzene rings is 5.8 (1)°; this near planarity could be due to conjugation or a packing effect. Intramolecular O—H⋯O and C—H⋯O hydrogen bonds occur. In the crystal, molecules are connected by O—H⋯O hydrogen bonds involving the hydroxy and carbonyl groups, forming hydrogen-bonded chains along  and [1-10]. The chains are linked by C—H⋯O interactions.
The title compound, C15H12BrClN2O2, was synthesized by the condensation of 1-(5-bromo-2-hydroxyphenyl)ethanone with 2-chlorobenzohydrazide in anhydrous ethanol. The Schiff base molecule displays a trans configuration with respect to the C=N double bond. The dihedral angle between the two benzene rings is 13.74 (3)°. The molecular conformation is stabilized by an intramolecular O—H⋯N and the crystal structure by intermolecular N—H⋯O hydrogen bonds.
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, C17H18N4O5·2C3H7NO, two solvent molecules are linked to the main molecule via N—H⋯O and O—H⋯O hydrogen bonds, forming a hydrogen-bonded trimer. Intramolecular O—H⋯N hydrogen bonds influence the molecular conformation of the main molecule, and the two benzene rings form a dihedral angle of 10.55 (18)°. In the crystal, intermolecular O—H⋯O hydrogen bonds link hydrogen-bonded trimers into ribbons extending along the b axis.
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 asymmetric unit of the title compound, C19H16N2O5S, contains four independent molecules (A, B, C and D), with two molecules (B and D) displaying disorder in their methylsulfanyl groups [occupancy ratios of 0.797 (11):0.203 (11) and 0.85 (2):0.15 (2)]. The nitro groups are twisted slightly out of the planes of the 2-pyrroline rings to which they are bonded with dihedral angles of 10.17 (1), 8.01 (1), 9.44 (1) and 8.87 (1)° in molecules A, B, C and D, respectively. The 2-pyrroline rings are almost orthogonal to the attached tolyl rings, forming dihedral angles of 73.44 (1), 81.21 (1), 88.18 (8) and 73.94 (1)° for molecules A, B, C and D, respectively. A weak intramolecular O—H⋯O interaction is observed in molecules B and C. The two hydroxy groups in each molecule are involved in intermolecular O—H⋯O hydrogen bonding. In the crystal, molecules are connected via O—H⋯O and C—H⋯O hydrogen bonds, forming a complex three-dimensional network.
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 title compound, C25H33FN2O4, was synthesized from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-12-methylene-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-13-one), which was isolated from the chloroform extract of the aerial parts of Anvillea radiata. The asymmetric unit contains two independent molecules. In each molecule, the ten-membered ring displays an approximative chair–chair conformation. Each of the piperazine rings adopts a perfect chair conformation, while both lactone rings show an envelope conformation, one with the C atom bearing the piperazin-1-ylmethyl group as the flap, the other with the junction C atom not attached to the ring O atom as the flap. The dihedral angles between the least-squares planes through the ten- and five-membered rings in the two molecules are similar [19.1 (3) and 16.2 (3)°]. An intramolecular O—H⋯N hydrogen bond stabilizes the molecular conformation. The crystal packing is stabilized by C—H⋯O hydrogen bonds.
In the title compound, C19H16O3, an intramolecular O—H⋯O=C hydrogen bond is formed between the hydroxy and carbonyl groups on the naphthalene ring system, resulting in an S(6) ring. The angles between the C=O bond vector and the least-squares planes of the naphthalene ring system and the benzene ring are 27.63 (6) and 47.99 (7)°, respectively. The dihedral angle between the latter planes is 61.39 (5)°. In the crystal, two molecules are connected by pairs of intermolecular O—H⋯O=C hydrogen bonds, forming centrosymmetric dimers with an R
2(4) graph-set motif. The molecular packing features C—H⋯π interactions.