In the title compound, C14H11BrN2O4, the amide segment makes dihedral angles of 23.4 (2) and 20.5 (2)° with the benzene rings, while the dihedral angle between the bezene rings is 2.90 (8)°. The nitro and methoxy groups are almost coplanar with their bound benzene ring, with the r.m.s. deviation for the 11 non-H atoms being 0.0265 (1) Å. An intramolecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, molecules are linked into [2-10] chains by weak C—H⋯O and C—H⋯Br interactions, which form an R
2(8) motif between pairs of molecules in the chain. A Br⋯O [3.2018 (12) Å] short contact also occurs.
In the title compound, C12H10N2O4, the pyridine and benzene rings are almost orthogonal, forming a dihedral angle of 86.63 (6)°. Each of the nitro [O—N—C—C torsion angle = −6.45 (19)°] and methoxy [C—O—C—C torsion angle = 179.69 (11)°] groups is almost coplanar with the ring to which it is connected. Molecules are consolidated in the crystal structure via C—H⋯O interactions, forming a three-dimensional network.
The asymmetric unit of the title compound, C24H21FN2O5S, consists of two crystallographically independent molecules. In each molecule, the central dihydropyrimidine ring is significantly puckered and adopts a conformation which is best described as an intermediate between a boat and a screw boat. The least-squares planes of the dihydropyrimidine rings are almost coplanar with the fluoro-substituted benzene rings, making dihedral angles of 9.04 (7) and 6.68 (7)°, and almost perpendicular to the methoxy-substituted benzene rings with dihedral angles of 89.23 (7) and 88.30 (7)°. In the molecular structure, S(6) ring motifs are formed by C—H⋯O and C—H⋯S hydrogen bonds. In the crystal, molecules are linked into a three-dimensional network by intermolecular C—H⋯O and C—H⋯F hydrogen bonds. The crystal structure is further stabilized by a C—H⋯π interaction.
In the title compound, C14H12ClNO2, the chloro- and methoxy-substituted benzene rings are close to orthogonal [dihedral angle = 79.20 (3)°]. These rings also make angles of 45.9 (3) and 33.5 (3)° with the amide –CONH– unit. The methoxy substituent lies close to the methoxybenzene ring plane, with a maximum deviation of 0.142 (3) Å for the methyl C atom. The N—H bond is anti to the 2-chloro substituent of the aniline ring. In the crystal structure, intermolecular N—H⋯O hydrogen bonds form C(4) chains augmented by a weak C—H⋯O interaction involving an ortho H atom of the methoxy benzene ring that generates an R
1(6) motif. The chains stack the molecules into columns down the b axis. Adjacent columns are linked by additional C—H⋯O and C—H⋯π contacts, generating a three-dimensional network.
The title compound crystallized with two independent molecules in the asymmetric unit. In the crystal, they are linked to one another, forming chains enclosing (10) and (12) ring motifs.
The title compound, C22H17NO4, crystallizes with two independent molecules (A and B) in the asymmetric unit. Each molecule exists as an E isomer with C—C=C—C torsion angles of −175.69 (17) and −178.41 (17)° in A and B, respectively. In molecule A, the planes of the terminal benzene rings are twisted by an angle of 26.67 (10)°, while the biphenyl unit is non-planar, the dihedral angle between the rings being 30.81 (10)°. The dihedral angle between the nitrophenyl ring and the inner phenyl ring is 6.50 (9)°. The corresponding values in molecule B are 60.61 (9), 31.07 (8) and 31.05 (9)°. In the crystal, molecules are arranged in a head-to-head manner, with the 3-nitrophenyl groups nearly parallel to one another. The A and B molecules are linked to one another via C—H⋯O hydrogen bonds, forming chains lying parallel to (-320) and enclosing R
2(10) and R
2(12) ring motifs. The methoxy group in both molecules is positionally disordered with a refined occupancy ratio of 0.979 (4):0.021 (4) for molecule A and 0.55 (4):0.45 (4) for molecule B.
crystal structure; chalcones; C—H⋯O hydrogen bonding; main-residue disorder
Molecules of the title compound, C16H16N4O7, are not planar with a dihedral angle of 5.50 (11)° between the substituted benzene rings. The two meta-methoxy groups of the 3,4,5-trimethoxybenzene moiety lie in the plane of the attached ring [Cmethyl–O–C–C torsion angles −0.1 (4)° and −3.7 (3)°] while the para-methoxy substituent lies out of the plane [Cmethyl—O—C—C, −86.0 (3)°]. An intramolecular N—H⋯O hydrogen bond involving the 2-nitro substituent generates an S(6) ring motif. In the crystal structure, molecules are linked by weak C—H⋯O interactions into screw chains, that are arranged into a sheet parallel to the bc plane. These sheets are connected by π–π stacking interactions between the nitro and methoxy 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 compound, C14H12ClNO4S, crystallizes with two molecules in the asymmetric unit. The dihedral angles between the benzene rings are 89.68 (1) (molecule 1) and 82.9 (1)° (molecule 2). In each molecule, intramolecular N—H⋯O hydrogen bonds between the amide H atom and the methoxy O atom generate S(6) loops. In the crystal, molecule 2 is linked into inversion dimers through pairs of C—H⋯O interactions, forming an R
2(8) ring motif. Molecules 1 and 2 are further linked along the b-axis direction through C—H⋯π interactions. The crystal structure is further stabilized by several π–π stacking interactions [centroid–centroid separations = 3.7793 (1), 3.6697 (1) and 3.6958 (1) Å], thus generating a three-dimensional architecture.
In the title compound, C26H27BrN2O, the piperidine ring has a chair conformation and all ring substituents occupy equatorial positions, apart from the double-bonded N atom, which occupies a bisectional position. The dihedral angle formed between the phenyl rings is 61.18 (19)°, and the phenyl rings form dihedral angles of 49.78 (19) and 69.2 (18)° with the bromobenzene ring. The latter is coplanar with the methoxy(methylidene)amine fragment [N—O—C—C torsion angle = −171.7 (2)°]. Linear supramolecular chains, approximately along , sustained by C—H⋯π interactions, feature in the crystal packing.
In the title compound, C17H14N2O6, the conformation about the C=C double bond [1.345 (2) Å] is E, with the ketone moiety almost coplanar [C—C—C—C torsion angle = 9.5 (2)°] along with the phenyl ring [C—C—C—C = 5.9 (2)°]. The aromatic rings are almost perpendicular to each other [dihedral angle = 86.66 (7)°]. The 4-nitro moiety is approximately coplanar with the benzene ring to which it is attached [O—N—C—C = 4.2 (2)°], whereas the one in the ortho position is twisted [O—N—C—C = 138.28 (13)°]. The molecules associate via C—H⋯O interactions, involving both O atoms from the 2-nitro group, to form a helical supramolecular chain along . Nitro–nitro N⋯O interactions [2.8461 (19) Å] connect the chains into layers that stack along .
crystal structure; hydrogen bonding; N⋯O interactions
In the title moleclue, C16H14O4, the dihedral angle between the benzene rings is 16.1 (3)°. The methoxy group is essentially coplanar with the benzene ring to which it is attached, with a C—O—C C torsion angle of 5.5 (9)°. In the crystal, molecules are linked by O—H⋯O and bifurcated O—H⋯(O,O) hydrogen bonds, forming a three-dimensional network. The structure was refined as a two-component inversion twin.
crystal structure; prop-2-en-1-one; chalcones; biological activity; hydrogen bonding
In the title compound, C14H12ClNO2, the mean plane through the amide group [–N—C=O–] forms dihedral angles of 27.55 (8) and 31.94 (7)° with the methoxy- and chloro-substituted benzene rings, respectively. The dihedral angle between the benzene rings is 59.24 (4)°. In the crystal, N—H⋯O and weak C—H⋯O hydrogen bonds link the molecules into chains along the a axis.
A significant twist is observed in the title molecule, C11H10N2O2, as seen in the dihedral angle between the pyrazine and benzene rings of 72.79 (8)°. The methoxy group is almost coplanar with the benzene ring to which it is attached [C—O—C—C torsion angle = 175.83 (15)°]. Centrosymmetric dimers are formed in the crystal structure which are held together by weak π–π interactions between pyrazine rings [centroid–centroid distance = 3.8534 (10) Å].
In the asymmetric unit of the title compound, C18H20N2O5, there are two crystallographic independent molecules. Both molecules are twisted; the dihedral angle between the two benzene rings is 7.2 (5)° in one molecule, whereas it is 85.9 (4)° in the other. Of the three methoxy groups in the 3,4,5-trimethoxyphenyl unit, two methoxy groups at meta positions are approximately coplanar with the benzene plane [C—O—C—C torsion angles of −2.3 (13)–4.8 (11)°], but the other methoxy, at the para position, is out of the plane [C—O—C—C of 72.8 (9)° in one molecule and −77.5 (9)° in the other]. In the crystal, molecules are linked by N—H⋯O hydrogen bonds and weak C—H⋯O interactions into tapes along the b axis. C—H⋯π interactions are also present.
The title compound, C22H26O9, crystallizes with two independent molecules in the asymmetric unit in which the dihedral angles between the two benzene rings are 21.4 (2) and 5.1 (2)°. An intramolecular O—H⋯O hydrogen bond occurs in each molecule. Intermolecular C—H⋯O hydrogen bonds stabilize the crystal structure.
In the title compound, C21H18O4, the C=C bond of the central enone group adopts an E conformation. The dihedral angle formed by the benzene ring and the naphthalene ring system is 6.60 (2)°. The methoxy groups on the benzene ring are essentially coplanar with the ring; the C—C—O—C torsion angles being 1.6 (2) and −177.1 (1)°. The hydroxy group attached to the naphthalene ring is involved in an intramolecular O—H⋯O hydrogen bond. The relative conformation of the two double bonds in the enone group is s-cisoid. In the crystal, weak C—H⋯O hydrogen bonds link the molecules into chains propagating along .
crystal structure; chalcone; enone; benzochalcone; naphthalene
The title salt crystallized as the monohydrate C15H16NO2
−·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 hydroxy and methoxy 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 [Cmethyl—O—C—C torsion angle = −0.8 (4)°]. In the crystal, the cations and anions are stacked by π–π interactions, with centroid–centroid distances of 3.7818 (19) and 3.9004 (17) Å. The cations, anions and water molecules are linked by O—H⋯O hydrogen bonds and weak C—H⋯O interactions, forming a three-dimensional network.
In the title 3-cyanopyridine derivative, C21H19N3O4, the 3-cyano-substituted pyridine ring forms dihedral angles of 2.35 (5) and 41.60 (5)° with the unsubstituted pyridine and 2,4,5-trimethoxy-substituted benzene rings, respectively. The dihedral angle between the unsubstituted pyridine and benzene rings is 39.84 (5)°. The methoxy groups form Cmethyl—O—C—(C,N) torsion angles in the range 0.80 (15)–11.45 (15)°. In the crystal, molecules related by 21 screw axes are linked by weak C—H⋯N hydrogen bonds along . In addition, weak C—H⋯π interactions and π–π stacking interactions between pyridine rings, with a centroid–centroid distance of 3.6448 (6) Å, are observed.
In the title molecule, C21H19N3O2, the central pyridine ring makes dihedral angles of 14.46 (9) and 34.67 (8)° with the 4-amino- and 4-ethoxy-substituted benzene rings, respectively. The ethoxy group is essentially coplanar with the attached benzene ring [C—O—C—C torsion angle = 178.70 (16)°] as is the methoxy group with the pyridine ring [C—O—C—N torsion angle = −3.0 (3)°]. In the crystal, molecules are linked by N—H⋯N hydrogen bonds into chains along . Weak C—H⋯O hydrogen bonds and C—H⋯π interactions are also present.
The title compound, C15H12N2O2S, is a P21/c polymorph of a previously reported P21/n polymorph [Büyükgüngör et al. (2004 ▶). Acta Cryst. E60, o1414–o1416]. The dihedral angle between the benzothiazole (r.m.s. deviation = 0.010 Å) and the benzene ring of 7.86 (6)° compares with 10.76 (10)° in the literature structure. The methoxy substituent is almost coplanar with the benzene ring to which it is attached [C—O—C—C torsion angle = 178.31 (14)°] and the conformation about the imine bond [1.287 (2) Å] is E. There is an intramolecular O—H⋯N hydrogen bond and the hydroxy O and thioether S atoms are syn. In the crystal, columns are formed along the b axis as centrosymmetric dimeric aggregates, mediated by C—H⋯O interactions and linked by π–π interactions between the thiazole and benzene rings [centroid-to-centroid distance = 3.8256 (10) Å].
In the title compound, C28H24O6·CHCl3, the two 4-methoxybenzoyl groups at the 1- and 8-positions of the naphthalene ring system are aligned almost antiparallel, the benzene rings making a dihedral angle of 25.76 (7)°. The naphthalene ring system makes dihedral angles of 72.51 (7) and 73.33 (7)° with the benzene rings. In the crystal, the naphthalene molecules are linked by C—H⋯O interactions, forming a helical chain along the b-axis direction. A C—H⋯Cl interaction is also observed between the aroylated naphthalene and chloroform molecules. The chloroform molecule is disordered over two positions with site occupancies of 0.478 (5) and 0.522 (5).
In the title compound, C28H18F4O2, the central benzene ring makes dihedral angles of 44.27 (6), 56.33 (5) and 77.27 (6)° with the two adjacent fluorobenzene rings and terminal difluoro-substituted benzene ring, respectively. The dihedral angle between the fluorobenzene rings is 87.81 (6)°. The methoxy and prop-2-en-1-one groups are essentially coplanar with their attached benzene rings, as indicated by their C—O—Car—Car [−0.06 (15)°] and C—C—Car—Car [4.5 (2)°] (ar = aromatic) torsion angles. In the crystal, molecules are linked by C—H⋯F and C—H⋯O hydrogen bonds into sheets lying parallel to the ac plane. The crystal structure also features C—H⋯π interactions.
The title N-benzylphthalimide derivative, C16H13NO3, consists of two planar moieties, viz. the phthalimide system (r.m.s. deviation = 0.007 Å) and the phenyl ring, which make a dihedral angle of 84.7 (6)°. The methoxy group is almost coplanar with the phathalimide ring, as shown by the C—C—O—C torsion angle of −171.5 (2)°. In the crystal, the molecules are self-assembled via non-classical C—H⋯O hydrogen bonds, forming a tape motif along .
In the title compound, C21H19NO6, the isoindole ring system is essentially planar [maximum deviation = 0.019 (2) Å for the N atom] and is oriented at a dihedral angle of 51.3 (1)° with respect to the benzene ring. The two methoxy groups are almost coplanar with the attached benzene ring [C—O—C—C = 3.7 (4) and 4.3 (4)°]. The molecular conformation is stabilized by an intramolecular C—H⋯O hydrogen bond, which generates an S(9) ring motif. In the crystal, molecules are linked through bifurcated C—H⋯(O,O) hydrogen bonds having R
2(5) ring motifs, forming chains along the b-axis direction. The crystal packing is further stabilzed by π–π interactions [centriod–centroid distance = 3.463 (1) Å].
There are two crystallographically independent molecules in the asymmetric unit of the title compound, C15H14N4O5, with different conformations for the methoxy groups. The molecules are both slightly twisted, the dihedral angles between two benzene rings being 8.37 (18)° in one and 7.31 (18)° in the other. In both molecules, the two nitro groups are essentially coplanar with their bound benzene ring, with the r.m.s. deviation of the dinitrobenzene plane being 0.0310 (3) Å in one molecule and 0.0650 (3) Å in the other. In each molecule, an intramolecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, molecules are linked by weak C—H⋯O interactions and stacked along the a axis through π–π interactions, with centroid–centroid distances of 3.651 (2) and 3.721 (2) Å. The crystal studied was a non-merohedral twin with a refined minor component of 20.1 (3)%.
The title compound crystallizes as a hemihydrate, C18H20N2O5·0.5H2O. The molecule exists in an E conformation with respect to the C=N imine bond. The 4-methoxyphenyl 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-methoxy-substituted ring. All methoxy substituents lie close to the plane of the attached benzene rings [the Cmethyl—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  via N—H⋯O and O—H⋯O hydrogen bonds and weak C—H⋯O interactions.