Packing in the title keto ester compound is dominated by the formation of inversion dimers by both non-classical hydrogen bonds and offset π–π stacking interactions.
2-(4-Chlorophenyl)-2-oxoethyl 3-bromobenzoate, C15H10BrClO3, was synthesized in a single-step reaction by condensation of 3-bromobenzoic acid with 2-bromo-1-(4-chlorophenyl)ethanone in dimethylformamide in the presence of triethylamine as a catalyst. The structure consists of an aryl ketone moiety linked to an aryl ester unit by a methylene group. Both units are reasonably planar (r.m.s. deviations of 0.119 and 0.010 Å for the aryl ketone and aryl ester units, respectively) and are almost orthogonal, with an angle of 88.60 (3)° between them. In the crystal, molecules form five separate sets of inversion dimers. Three of these are generated by two C—H⋯O interactions and a C—H⋯Br contact, and form chains along c and along the ab cell diagonal. In addition, two inversion-related π–π stacking interactions between like aryl rings again form chains of molecules but in this instance along the bc diagonal. These contacts generate infinite layers of molecules parallel to (011) and stack the molecules along the a-axis direction.
crystal structure; 2-(4-chlorophenyl)-2-oxoethyl 3-bromobenzoate; synthesis; π–π interactions; inversion dimers
The title compound, C15H11ClO4, consists of a chlorobenzene ring and a phenol ring which are linked together by a 1,4-dioxo-2-oxabutane-1,4-diyl group. The dihedral angle between the chlorobenzene and phenol rings is 65.70 (11)°. In the crystal, intermolecular O—H⋯O hydrogen bonds link the molecules into chains along .
The asymmetric unit of the title compound, C15H10ClNO4S, contains two independent conformers wherein the 2-chlorophenyl group in one is rotated by approximately 180° compared to the other molecule. This affects the S—N—C—C(=O) and N—C—C(=O)—C torsion angles giving vlaues of −87.0 (2) and 158.7 (2)° in one molecule and −104.3 (2) and −173.4 (2)° in the other. The benzisothiazole ring systems in the two molecules are essentially planar (r.m.s. deviations = 0.017 and 0.010 Å) and form dihedral angles of 73.53 (7) and 73.26 (6)° with the benzene rings. In the crystal, there are weak π–π interactions between the benzene rings of the benzisothiazole groups and symmetry-related chlorobenzene rings with centroid–centroid distances of 3.6178 (13) and 3.6267 (15) Å. In addition, pairs of weak intermolecular C—H⋯O hydrogen bonds form inversion dimers which are connected by further C—H⋯O hydrogen bonds into a three-dimensional network.
In the title compound, C17H15ClO5, the benzene rings forms a dihedral angle of 74.45 (10)°. In the crystal, molecules are linked into C(13) chains along  via C—H⋯O hydrogen bonds. The crystal packing also features short Cl⋯Cl contacts of 3.1253 (10) Å.
In the title compound, C16H13ClO4, the two benzene rings make a dihedral angle of 86.38 (8)°. In the crystal, intermolecular C—H⋯O hydrogen bonds link the molecules to form columns along the a axis. The molecules are also stabilized by a π–π stacking interaction, with a centroid–centroid distance of 3.7793 (10) Å between the inversion-related benzene rings.
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, C16H13BrO3, the dihedral angle formed between the bromo- and methyl-substituted benzene rings is 66.66 (8)°. In the crystal, molecules are linked by intermolecular C—H⋯O hydrogen bonds, forming a two-dimensional network parallel to the ac plane. The crystal packing is further consolidated by C—H⋯π interactions.
In the title compound, C16H13BrO4, the benzene rings are almost perpendicular to each other, making a dihedral angle of 84.07 (8)°. In the crystal, the molecules are linked into chains along the a axis via intermolecular C—H⋯O hydrogen bonds. A C—H⋯π interaction is also observed.
In the title compound, C23H15BrO3, the anthracene ring system is essentially planar [maximum deviation = 0.29 (2) Å] and makes a dihedral angle of 5.74 (8)° with the mean plane of the bromo-substituted benzene ring. An intramolecular C—H⋯O hydrogen bond generates an S(9) ring motif. In the crystal, molecules are linked by C—H⋯O interactions, forming a two-dimensional network parallel to the ac plane. π–π stacking interactions are observed between benzene rings [centroid–centroid distances = 3.5949 (14) and 3.5960 (13) Å].
The title compound, C16H13BrO3, consists of a toluene ring and a bromobenzene ring which are linked together by a 2-oxopropyl acetate group. The dihedral angle formed between the toluene and bromobenzene rings is 80.70 (7)°. In the crystal, intermolecular C—H⋯O hydrogen bonds link the molecules into a three-dimensional network.
In the title molecule, C16H13BrO4, the dihedral angle between the benzene rings is 85.92 (10)°. In the crystal, molecules are linked into chains along  via weak intermolecular C—H⋯O hydrogen bonds.
The crystal structure of the title compound (4CP4MBA), C14H11ClO2, resembles those of 3-chlorophenyl 4-methylbenzoate (3CP4MBA), 4-methylphenyl 4-methylbenzoate (4MP4MBA), 4-methylphenyl 4-chlorobenzoate (4MP4CBA) and other aryl benzoates with similar bond parameters. The dihedral angle between the benzene rings in 4CP4MBA is 63.89 (8)°, compared with 71.75 (7)° in 3CP4MBA, 63.57 (5)° in 4MP4MBA and 51.86 (4)° in 4MP4CBA. In the crystal structure of the title compound, the molecules are linked into an infinite chain along the a axis via C—H—O hydrogen bonds.
The asymmetric unit of the title compound, C15H10BrNO4S, contains two different conformers in which the benzisothiazole rings are essentially planar, with r.m.s. deviations of 0.012 and 0.017 Å. The mean planes of the benzene rings form dihedral angles 70.49 (13) and 72.79 (11)° with the benzisothiazole rings. The orientation of the Br atoms in the two conformers exhibit the most pronounced difference, with opposing orientations in the two molecules. The crystal structure is stabilized by π–π interactions between the benzene rings of the benzisothiazole moieties of one molecule and bromobenzene rings of the other molecule, with distances between the ring centroids of 3.599 (3) and 3.620 (3) Å, respectively. The crystal packing is further consolidated by pairs of weak intermolecular C—H⋯O hydrogen bonds, which form inversion dimers.
In the title compound, C16H13FO4, the dihedral angle between the benzene rings is 84.28 (8)°. In the crystal, C—H⋯F and C—H⋯O hydrogen bonds link the molecules to form a three-dimensional network. The crystal structure is consolidated by C—H⋯π interactions and short F⋯F contacts [2.7748 (14) Å] also occur.
In the title compound, C16H10ClF3O3, the two benzene rings are slightly twisted from each other, with a dihedral angle of 15.50 (8)° between the planes. In the crystal, intermolecular C—H⋯O hydrogen bonds link the molecules into a layer parallel to the bc plane.
In the title compound, C16H12Cl2O4, the dihedral angle between the benzene rings is 70.11 (6)°. In the crystal, molecules are linked by C—H⋯O hydrogen bonds into a three-dimensional network. A C—H⋯π interaction is also observed.
The asymmetric unit of title compound, C15H9ClF2O3, consists of two crystallographically independent molecules. The dihedral angle between the two terminal benzene rings in one molecule is 7.92 (14)°, while that in the other molecule is 73.50 (16)°. In the crystal, molecules are stacked into columns along the b axis by intermolecular C—H⋯O hydrogen bonds. A π–π interaction with a centroid-to-centroid distance of 3.747 (2) Å further stabilizes the crystal structure.
The title compound, C23H17FN2O3, crystallizes with two independent molecules in the asymmetric unit. The molecules are connected by pairs of N—H⋯O hydrogen bonds and have slightly different conformations, as indicated by the dihedral angles between the central imidazolidine-2,4-dione ring and its three substituents. In one molecule, these are 60.56 (1) and 82.66 (9)° to the phenyl rings and 84.35 (16)° to the 2-(4-fluorophenyl)-2-oxoethyl side chain. In the other molecule, the corresponding angles are 66.35 (10), 84.94 (9) and 86.31 (16)°. In the crystal, weak C—H⋯O interactions leading to a three-dimensional supramolecular architecture.
The asymmetric unit of the title compound, C15H10BrClO3, consists of three crystallographically independent molecules. The dihedral angles between the benzene rings in the three molecules are 68.8 (2), 0.7 (3) and 66.1 (2)°. In the crystal, the three independent molecules are interconnected by C—H⋯O hydrogen bonds, leading to isolated trimers.
The asymmetric unit of the title compound, C15H10Br2O3, consists of three crystallographically independent molecules (A, B and C). The phenyl rings in molecules A, B and C make dihedral angles of 6.1 (3), 3.2 (2) and 54.6 (2)° to each other, respectively. In the crystal, molecules are linked into two-dimensional layers parallel to the ab plane by intermolecular C—H⋯O hydrogen bonds. The crystal structure is further stabilized by C—H⋯π interactions. The studied crystal is an inversion twin, the refined ratio of the twin components being 0.128 (8):0.872 (8).
In the title compound, C15H11BrO4, the dihedral angle between the aromatic rings is 66.77 (8)°. In the crystal, O—H⋯O, C—H⋯Br and C—H⋯O hydrogen bonds link the molecules, forming layers lying parallel to (101). The crystal packing is further consolidated by C—H⋯π interactions and π–π stacking interactions [centroid–centroid distance = 3.5476 (7) Å].
In the title compound, C16H10F4O3, the fluoroform group is disordered over two orientations with an occupancy ratio of 0.834 (4):0.166 (4). The dihedral angle between the two aromatic rings is 20.34 (9)°. In the crystal, C—H⋯O hydrogen bonds link the molecules into layers lying parallel to the bc plane.
In the title compound, C14H16N6O6·C2H6O·H2O, both substituents of the benzene ring are approximately planar with maximum deviations from the mean plane of 0.0561 (12) (an imine N atom) and 0.1419 (11) Å (a methoxy O atom). The substituents are tilted out of the plane of the benzene ring by 64.48 (4) and 70.08 (5)°, respectively. In the crystal, molecules form centrosymmetric dimers associated via pairs of N—H⋯O hydrogen bonds. The dimers are linked via the water and ethanol molecules, forming two-dimensional hydrogen-bond networks lying parallel to (100).
In the title compound, C15H11ClO3, the dihedral angle between the aromatic rings is 84.29 (8)°. In the crystal, molecules are linked by weak C—H⋯π interactions.
In the title compound, C26H28FN5O3, the morpholine ring adopts a chair conformation. The piperazine ring is puckered [Q
T = 0.5437 (15) Å, θ = 8.89 (15) and ϕ = 357.2 (11)°]. The 1,6-dihydropyridazine ring makes dihedral angles of 28.03 (7) and 77.46 (7)° with the phenyl and benzene rings, respectively. In the crystal, molecules are linked along the c axis by C—H⋯O interactions and are flattened parallel to the ac plane. C–H⋯π interactions also contribute to the stability of the structure.