3,6,11-trihy-droxy-1,1-dimethyl-2,3-di-hydro-chromeno[2,3-f]chromen-7-one monohydrate), known as pruniflorone N, crystallized as a monohydrate, C18H16O6·H2O. The three ring systems of the xanthone skeleton are approximately coplanar, with an r.m.s. deviation of 0.0270 (1) Å from the plane through the 14 non-H atoms. The O atoms of the two hy-droxy substituents on the benzene rings also lie close to this plane, with deviations of 0.019 (1) and 0.070 (1) Å. The 2'-hy-droxy-4',4'-di-methyl-pyran ring is disordered over two positions with a 0.798 (3):0.202 (3) site-occupancy ratio. An intra-molecular O-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, the xanthone and water mol-ecules are linked into a three-dimensional network by O-H⋯O hydrogen bonds and weak C-H⋯O inter-actions. π-π inter-actions, with centroid-centroid distances of 3.5982 (7), 3.6081 (7) and 3.6456 (7) Å, are also observed.
The asymmetric unit of the title hydrated salt, C22H25N2 (+)·C6H4ClO3S(-)·H2O, comprises two 2-[4-(di-ethyl-amino)-styr-yl]-1-methyl-quinolin-1-ium cations, two 4-chloro-benzene-sul-fon-ate anions and two solvent water mol-ecules. One ethyl group of both cations displays disorder over two positions in a 0.659 (2):0.341 (2) ratio in one mol-ecule and in a 0.501 (2):0.499 (2) ratio in the other. The sulfonate group of one anion is also disordered over two positions in a 0.893 (7):0.107 (7) ratio. The dihedral angle between the mean plane of the quinolinium ring system and that of benzene ring is 10.57 (18)° in one cation and 14.4 (2)° in the other. In the crystal, cations, anions and water mol-ecules are linked into chains along the [010] direction by O-H⋯Osulfonate hydrogen bonds, together with weak C-H⋯Osulfonate and C-H⋯Cl inter-actions. The cations are stacked by π-π inter-actions, with centroid-centroid distances in the range 3.675 (2)-4.162 (3) Å.
The asymmetric unit of the title salt, C36H32N2 (2+)·2C6H4ClO3S(-), consists of one anion and one half-cation, the other half being generated by inversion symmetry. The dihedral angle between the pyridinium ring and the napthalene ring system in the asymmetric unit is 42.86 (6)°. In the crystal, cations and anions are linked by weak C-H⋯O inter-actions into chains along [010]. Adjacent chains are further arranged in an anti-parallel manner into sheets parallel to the bc plane. π-π inter-actions are observed involving the cations, with centroid-centroid distances of 3.7664 (8) and 3.8553 (8) Å.
The title compound crystallizes as a hemihydrate, C18H20N2O5·0.5H2O. The mol-ecule exists in an E conformation with respect to the C=N imine bond. The 4-meth-oxy-phenyl unit is disordered over two sets of sites with a refined occupancy ratio of 0.54 (2):0.46 (2). The dihedral angles between the benzene rings are 29.20 (9) and 26.59 (9)°, respectively, for the major and minor components of the 4-meth-oxy-substituted ring. All meth-oxy substituents lie close to the plane of the attached benzene rings [the Cmeth-yl-O-C-C torsion angles range from -4.0 (12) to 3.9 (2)°]. In the crystal, the components are linked into chains propagating along [001] via N-H⋯O and O-H⋯O hydrogen bonds and weak C-H⋯O inter-actions.
In the title mixed salt, 2C16H15N2 (+)·C6H4ClO3S(-)·NO3 (-), one of the cations shows whole mol-ecule disorder over two sets of sites in a 0.711 (7):0.289 (7) ratio. The 4-chorobenzenesulfon-ate anion is also disordered over two orientations in a 0.503 (6):0.497 (6) ratio. The cations are close to planar, the dihedral angles between the pyridinium and indole rings being 1.48 (3)° in the ordered cation, and 5.62 (3) and 2.45 (3)°, respectively, for the major and minor components of the disordered cation. In the crystal, the cations are stacked in an anti-parallel manner approximately along the a-axis direction and linked with the anions via N-H⋯O hydrogen bonds and C-H⋯O inter-actions, generating a three-dimensional network. Weak C-H⋯π and π-π inter-actions [with centroid-centroid distances of 3.561 (2)-3.969 (7) Å] are also observed.
The title salt crystallized as the monohydrate C15H16NO2 (+)·C6H4BrSO3 (-)·H2O. The cation exists in an E conformation with respect to the ethynyl bond and is essentially planar, with a dihedral angle of 6.52 (14)° between the pyridinium and the benzene rings. The hy-droxy and meth-oxy substituents are coplanar with the benzene ring to which they are attached, with an r.m.s. deviation of 0.0116 (3) Å for the nine non-H atoms [Cmeth-yl-O-C-C torsion angle = -0.8 (4)°]. In the crystal, the cations and anions are stacked by π-π inter-actions, with centroid-centroid distances of 3.7818 (19) and 3.9004 (17) Å. The cations, anions and water mol-ecules are linked by O-H⋯O hydrogen bonds and weak C-H⋯O inter-actions, forming a three-dimensional network.
There are two independent mol-ecules in the asymmetric unit of the title compound, C16H17NO4, with similar conformations but some differences in their bond angles. Each mol-ecule adopts a trans configuration with respect to the methyl-idene C=N bond and is twisted with a dihedral angle between the two substituted benzene rings of 80.52 (7)° in one mol-ecule and 83.53 (7)° in the other. All meth-oxy groups are approximately coplanar with the attached benzene rings, with Cmeth-yl-O-C-C torsion angles ranging from -6.7 (2) to 5.07 (19)°. In the crystal, independent mol-ecules are linked together by O-H⋯N and O-H⋯O hydrogen bonds and a π-π inter-action [centroid-centroid distance of 3.6030 (9) Å], forming a dimer. The dimers are further linked by weak C-H⋯O inter-actions and another π-π inter-action [centroid-centroid distance of 3.9452 (9) Å] into layers lying parallel to the ab plane.
In the title hydrated molecular salt, C22H25N2 (+)·C6H4FO3S(-)·H2O, the cation displays whole mol-ecule disorder over two sets of sites in a 0.780 (5):0.220 (5) ratio. The quinolinium ring system is essentially planar, with r.m.s. deviations of 0.0162 and 0.0381 Å for the major and minor disorder components, respectively. The dihedral angles between the mean plane of the quinolinium ring system and the benzene ring are 5.1 (3) and 7.7 (11)°, respectively, for the major and minor components in the cation. In the crystal, cations, anions and water mol-ecules are linked into chains along [010] by O-H⋯O hydrogen bonds and are further connected into a three-dimensional network by weak C-H⋯O and C-H⋯F inter-actions. In addition, π-π inter-actions with centroid-centroid distances of 3.634 (3), 3.702 (5) and 3.838 (5) Å are observed.
The title compound, C16H16N4O7, is close to being planar, with a dihedral angle of 3.15 (11)° between the benzene rings. The meth-oxy groups at the ortho- and para-positions of the 2,4,5-tri-meth-oxy-phenyl group are almost coplanar with the ring [deviations of the C atoms = 0.017 (2) and -0.025 (2) Å, respectively], whereas the meta-meth-oxy group deviates slightly [C-atom displacement = 0.162 (2) Å]. Both the ortho- and para-nitro groups are close to being coplanar with their attached ring [dihedral angles = 7.81 (12) and 8.56 (11)°, respectively]. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds involving the same H atom as the intra-molecular bond generate R 2 (2)(12) loops. The dimers are linked by weak C-H⋯O inter-actions into sheets parallel to the (10-4) plane and the sheets are stacked by π-π inter-actions, with a centroid-centroid distance of 3.5974 (14) Å.
The asymmetric unit of the title compound, C18H18ClN3OS·C2H5OH, comprises a pyrazoline derivative and an ethanol solvent mol-ecule. In the mol-ecule of the pyrazoline derivative, the pyrazole ring adopts an envelope conformation with the C atom bearing the eth-oxy-phenyl substituent as the flap. The dihedral angle between the benzene rings is 74.22 (7)°. The eth-oxy group is coplanar with the attached benzene ring [C-O-C-Cmeth-yl = 175.50 (11)° and r.m.s. deviation = 0.0459 (1) Å for the nine non-H atoms]. In the crystal, the pyrazoline mol-ecules are linked by N-H⋯Oeth-oxy hydrogen bonds into chains along the c axis and are further linked with the solvent ethanol mol-ecules by N-H⋯Oethanol and Oethanol-H⋯S hydrogen bonds. C-H⋯π inter-actions are also present.
The title compound, C15H14N2O3, crystallizes with two independent mol-ecules (A and B) in the asymmetric unit that differ in the orientation of the 3-meth-oxy-phenyl group with respect to the methyl-idenebenzohydrazide unit. The dihedral angles between the two benzene rings are 24.02 (10) and 29.30 (9)° in mol-ecules A and B, respectively. In mol-ecule A, the meth-oxy group is twisted slightly relative to its bound benzene ring, with a Cmeth-yl-O-C-C torsion angle of 14.2 (3)°, whereas it is almost co-planar in mol-ecule B, where the corresponding angle is -2.4 (3)°. In the crystal, the mol-ecules are linked by N-H⋯O, O-H⋯N and O-H⋯O hydrogen bonds, as well as by weak C-H⋯O inter-actions, forming sheets parallel to the bc plane. The N-H⋯O hydrogen bond and weak C-H⋯O inter-action link different mol-ecules (A⋯B) whereas both O-H⋯N and O-H⋯O hydrogen bonds link like mol-ecules (A⋯A) and (B⋯B). Pairs of inversion-related B mol-ecules are stacked approximately along the a axis by π-π inter-actions in which the distance between the centroids of the 3-meth-oxy-phenyl rings is 3.5388 (12) Å. The B mol-ecules also participate in weak C-H⋯π inter-actions between the 4-hy-droxy-phenyl and the 3-meth-oxy-phenyl rings.
Mol-ecules of the title compound, C16H16N4O7, are not planar with a dihedral angle of 5.50 (11)° between the substituted benzene rings. The two meta-meth-oxy groups of the 3,4,5-tri-meth-oxy-benzene moiety lie in the plane of the attached ring [Cmeth-yl-O-C-C torsion angles -0.1 (4)° and -3.7 (3)°] while the para-meth-oxy substituent lies out of the plane [Cmeth-yl-O-C-C, -86.0 (3)°]. An intra-molecular N-H⋯O hydrogen bond involving the 2-nitro substituent generates an S(6) ring motif. In the crystal structure, mol-ecules are linked by weak C-H⋯O inter-actions into screw chains, that are arranged into a sheet parallel to the bc plane. These sheets are connected by π-π stacking inter-actions between the nitro and meth-oxy substituted aromatic rings with a centroid-centroid separation of 3.9420 (13) Å. C-H⋯π contacts further stabilize the two-dimensional network.
The title aza-stilbene derivative, C14H13NO2 {systematic name: (E)-2-[(4-meth-oxy-benzyl-idene)amino]-phenol}, is a product of the condensation reaction between 4-meth-oxy-benzaldehyde and 2-amino-phenol. The mol-ecule adopts an E conformation with respect to the azomethine C=N bond and is almost planar, the dihedral angle between the two substituted benzene rings being 3.29 (4)°. The meth-oxy group is coplanar with the benzene ring to which it is attached, the Cmeth-yl-O-C-C torsion angle being -1.14 (12)°. There is an intra-molecular O-H⋯N hydrogen bond generating an S(5) ring motif. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds, forming zigzag chains along [10-1]. The chains are linked via C-H⋯π inter-actions, forming a three-dimensional structure.