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In the title compound, C16H15F2NO4, the dihedral angle between the three-membered ring and the quinoline ring system is 64.3 (3)°. In the crystal structure, intermolecular C—H⋯O hydrogen bonds link the molecules, forming a column running along [101].
doi:10.1107/S1600536808034715
PMCID: PMC2959496
PMID: 21581071
In the title molecule, C20H17ClN2O, the dihedral angle between the mean plane of the quinoline ring system and the benzene ring of the dihydroquinolinone moiety is 57.84 (8)°. In the crystal, molecules are linked into centrosymmetric dimers via pairs of intermolecular N—H⋯N hydrogen bonds. These dimers are further stabilized by weak π–π stacking interactions between pyridine rings with a centroid–centroid distance of 3.9414 (12) Å.
doi:10.1107/S1600536811028170
PMCID: PMC3213526
PMID: 22091105
In the title structure, C25H24FN3O5, a strong intramolecular O—H⋯O hydrogen bond is present between the carboxy group at the 3-position and the carbonyl group at the 4-position. In the crystal, molecules are held together by weak C—H⋯O, C—H⋯F and π–π [centroid–centroid distance 3.6080 (8) Å] interactions. The 1,4-dihydroquinoline ring and cyclopropyl group are not in the same plane, making an interplanar angle of 57.52 (8)°.
doi:10.1107/S1600536812028711
PMCID: PMC3394047
PMID: 22798912
In the title compound, C19H15ClN2O, the quinoline ring forms a dihedral angle of 43.24 (1)° with the benzene ring of the dihydroquinolinyl system. In the crystal, molecules are linked through a single weak C—H⋯O hydrogen bond, forming ribbons which extend along (100), giving alternating zigzag molecular layers which stack down the b-axis direction.
doi:10.1107/S1600536812020831
PMCID: PMC3379295
PMID: 22719493
The title compound, C17H17FN4O4, is a derivative of ciprofloxacin [1-cyclopropyl-6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydroquinoline-3-carboxylic acid]. The crystal packing is stabilized by intermolecular C—H⋯O hydrogen bonds together with π–π electron ring interactions [centroid–centroid separations between quinoline rings of 3.5864 (11) and 3.9339 (13) Å]. A strong intramolecular O—H⋯O hydrogen bonds is present as well as an intramolecular C—H⋯F interaction.
doi:10.1107/S1600536809029729
PMCID: PMC2977261
PMID: 21583715
In the title layered coordination polymer, {[Cd(C17H18F2N3O3)(C8H4O4)]·3H2O}n, the CdII atom exhibits a very distorted CdO6 octahedral geometry defined by one O
3,O
4-bidentate 1-ethyl-6,8-difluoro-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate (lome) ligand, one O,O′-bidentate benzene-1,4-dicarboxylate (bdc) dianion and two O-monodentate bdc dianions. Both the bdc species in the asymmetric unit are completed by crystallographic inversion symmetry. The bridging bdc dianions link the cadmium nodes into a rectangular grid lying parallel to (01). A network of N—H⋯O and O—H⋯O hydrogen bonds helps to establish the packing.
doi:10.1107/S160053681004328X
PMCID: PMC3009166
PMID: 21588904
In the title compound, C18H14ClNO3, the dihydroquinolin-2-one ring system is almost planar (r.m.s. deviation = 0.033 Å). The carboxylate plane and the phenyl group are twisted away from the dihydroquinolin-2-one ring system by 50.3 (1) and 64.9 (1)°, respectively. In the crystal structure, inversion-related molecules form R
2
2(8) dimers via pairs of N—H⋯O hydrogen bonds.
doi:10.1107/S1600536809045425
PMCID: PMC2972051
PMID: 21578727
In the title compound, C20H14Cl2F3NO3, the trifluromethyl group is disordered over two sets of sites in a 0.784 (10):0.216 (10) ratio. The quinoline ring system is essentially planar with a maximum deviation of 0.058 (2) Å for the N atom and forms dihedral angles of 89.23 (11) and 8.13 (17)°, respectively with the mean planes of the benzene ring and the carboxylate group. In the crystal, pairs of weak C—H⋯O and C—H⋯F hydrogen bonds link molecules into centrosymmetric dimers. The crystal structure is further stabilized by weak π–π [centroid–centroid distance = 3.624 (2) Å] interactions.
doi:10.1107/S1600536812001249
PMCID: PMC3275192
PMID: 22347048
The title compound, C19H23F2N4O3
+·0.5SO4
2−·2.5H2O, an antibacterial fluoroquinolone, crystallized as a racemic twin (major twin component = 0.633) in the chiral space group P1. The asymmetric unit contains two sparfloxacinium cations, one sulfate anion and five molecules of water of solvation. The bond lengths and angles of both cations are almost identical. The quinoline ring systems in the cations are essentially planar, the mean deviations from the best plane being 0.045 (2) and 0.054 (2) Å and make π–π interactions with each other [centroid–centroid distances of 3.692 (4) Å and 3.744 (4) Å]. The crystal structure features intermolecular O—H⋯O, O—H⋯S, N+—H⋯O, N+—H⋯S and N—H⋯O hydrogen bonds together with intramolecular O—H⋯O and N—H⋯O hydrogen bonds. As a result, a three-dimensional supramolecular structure is observed.
doi:10.1107/S160053681104757X
PMCID: PMC3239011
PMID: 22199860
The asymmetric unit of the title compound, C13H10F3NO3, contains two independent molecules with similar conformations. In the crystal, N—H⋯O hydrogen bonds link alternating independent molecules into chains in [-110]. In the chain, the quinoline planes of the independent molecules are almost perpendicular to each other, forming a dihedral angle of 89.8 (1)°. π–π interactions between the aromatic rings of quinoline bicycles related by inversion centres [for two independent centrosymmetric dimers, the shortest centroid–centroid distances are 3.495 (1) and 3.603 (1) Å] link the hydrogen-bonded chains into layers parallel to (110). Weak C—H⋯F and C—H⋯O interactions further consolidate the crystal packing.
doi:10.1107/S1600536812045321
PMCID: PMC3588845
PMID: 23468810
The title compound, [Mn(C17H18FN3O3)2(C8H5O4)2]·2H2O or [Mn(cfH)2(1,2-Hbdc)2]·2H2O (cfH = ciprofloxacin = 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid, 1,2-bdc = benzene-1,2-dicarboxylate), has been prepared under hydrothermal conditions. The Mn2+ atom, located on an inversion centre, exhibits a distorted octahedral geometry, coordinated by four O atoms from two symmetry-related zwitterionic ciprofloxacin ligands in the equatorial positions and two O atoms of two 1,2-Hbdc ligands in the axial positions. The complex molecules are linked into a two-dimensional network through N—H⋯O and OW—H⋯O hydrogen bonds. A strong intramolecular hydrogen bond between the carboxyl/carboxylate groups of the 1,2-Hbdc anion is also present. The layers are further extended through off-set aromatic π–π stacking interactions of cfH groups [centroid–centroid distance of 3.657 (2) Å] into the final three-dimensional supramolecular arrays.
doi:10.1107/S1600536811011615
PMCID: PMC3089319
PMID: 21754278
In the title compound, [Ni(C10H6NO3)2(H2O)4], the central NiII atom is located on an inversion center and coordinated in a slightly distorted octahedral geometry by two O atoms from two 2-oxo-1,2-dihydroquinoline-4-carboxylate ligands and four water molecules, all of which act as monodentate ligands. The crystal structure features an extensive network of intermolecular hydrogen-bonding interactions (O—H⋯O and N—H⋯O) and offset face-to-face π–π stacking interactions [centroid–centroid distances = 3.525 (3) and 3.281 (5) Å].
doi:10.1107/S1600536807065671
PMCID: PMC2960272
PMID: 21201341
The title compound, [Zn(C17H19FN3O3)2(H2O)]·2H2O or [Zn(pef)2(H2O)]·2H2O, where pef is 1-ethyl-6-fluoro-7-(4-methylpiperazin-4-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate, was synthesized under hydrothermal conditions. The ZnII atom exhibits a distorted ZnO5 square-pyramidal geometry defined by two bidentate O,O-bonded pef anions in the basal plane and one water molecule in the apical position. A network of O—H⋯O and O—H⋯N hydrogen bonds is formed between the ZnII complexes and the uncoordinated water molecules.
doi:10.1107/S1600536807068298
PMCID: PMC2960459
PMID: 21201277
The title compound, C19H13ClF2N2O3, was prepared by the reaction of (Z)-ethyl 3-amino-3-(4-chlorophenyl)-2-cyanoacrylate and 2,6-difluorobenzoyl chloride. The dihedral angle between the chlorobenzene and fluorobenzene rings is 37.0 (1)°. The ethyl group is disordered over two positions [occupancies = 0.52 (2):0.48 (2)]. In addition to intramolecular N—H⋯O and N—H⋯F hydrogen bonds, the crystal packing shows the molecules to be connected by intermolecular C—H⋯O and C—H⋯N hydrogen bonds.
doi:10.1107/S1600536808034818
PMCID: PMC2959890
PMID: 21581235
Sitafloxacin is a newly developed fluoroquinolone antibacterial drug. The crystal studied, C19H18ClF2N3O3·CH3OH, consists of one molecule of sitafloxacin and one methanol solvent molecule. The molecule of sitafloxacin is a zwitterion with a protonated primary amine group and a deprotonated carboxylate group. The cyclopropane ring and the CO2 group make dihedral angles of 79.5 (3) and 35.4 (4)°, respectively, with the fused ring system. The supramolecular structure is defined by N—H⋯O and O—H⋯O hydrogen bonds.
doi:10.1107/S160053681203632X
PMCID: PMC3435823
PMID: 22969669
The title compound, C32H23ClN2O4, has a quinoline, a chlorophenyl and an acenaphthalene ring system attached to a central pyrrolidine ring, which has three stereogenic centers. Nevertheless, the compound crystallizes as a racemate with two molecules of identical chirality in the asymmetric unit. They differ in the conformation of the five-membered pyrrolidine ring; in one molecule it has an envelope conformation, while in the other molecule it has a twisted conformation. In each molecule there is an intramolecular O—H⋯O hydrogen bond making an S(6) ring motif. In the crystal, pairs of N—H⋯O hydrogen bonds produce inversion dimers with R
2
2(8) motifs. There are also C—H⋯O interactions present. The crystal structure contains voids (60 Å3) within which there is no evidence of solvent molecules.
doi:10.1107/S1600536811048896
PMCID: PMC3239020
PMID: 22199868
In the molecule of the title homoallylic amine, C16H13ClF3N, the dihedral angle between the two benzene rings is 84.63 (4)°. Weak intramolecular N—H⋯F hydrogen bonds generate S(6) and S(5) ring motifs. In the crystal structure, weak intermolecuar N—H⋯F hydrogen bonds link molecules into centrosymmetric dimers which are arranged in molecular sheets parallel to the ac plane.
doi:10.1107/S1600536809012896
PMCID: PMC2977711
PMID: 21583847
In the crystal of title compound, C16H19FN3O+·C10H5O8
−·H2O, the water molecule and the ions are connected by intermolecular N—H⋯O and O—H⋯O hydrogen bonds and π–π stacking [centroid–centroid separation = 3.602 (1) Å] between the benzene ring and the pyridine ring, generating a three-dimensional supramolecular structure.
doi:10.1107/S1600536812008392
PMCID: PMC3297959
PMID: 22412762
In the title compound, C22H18N2O4S, the dihedral angle between the phenylsulfonyl ring and the methylphenyl ring is 67.78 (7)°. In the crystal, molecules are linked by weak intermolecular C—H⋯O interactions into a zigzag chain along the [101] direction.
doi:10.1107/S1600536811030455
PMCID: PMC3200724
PMID: 22058902
In the title complex, [Cu(NO3)2(C17H18FN3O3)2], the CuII ion is located on an inversion center. It exhibits a distorted octahedral geometry, being coordinated by six O atoms, four from two ciprofloxacin ligand molecules (L), which act as bidentate ligands, and two from two nitrate anions. In the ligand, the piperazine ring has a chair conformation and the quinoline system is essentially planar [maximum deviation = 0.097 (2) Å]. One of the nitrate O atoms is disordered over two positions [occupancy ratio = 0.51 (6):0.49 (6)]. There is a C—H⋯F interaction in the complex. In the crystal, molecules are linked via N—H⋯O hydrogen bonds generating a two-dimensional network lying parallel to (111). The presence of C—H⋯O interactions leads to the formation of a three-dimensional structure. The title complex was prepared by hydrothermal synthesis, and the hexahydrate form of this complex, synthesized by conventional methods, has been reported previously [Hernandez-Gil et al. (2009 ▶). Polyhedron, 28, 138–144].
doi:10.1107/S1600536812007830
PMCID: PMC3297282
PMID: 22412472
In the title compound, C24H20ClF2N3O3S, the essentially planar triazole ring (r.m.s. deviation = 0.001 Å) forms dihedral angles of 22.35 (10), 68.17 (10) and 42.01 (10)° with the mean planes of the trimethoxyphenyl, chlorophenyl and difluorophenyl rings, respectively. A weak intramolecular C—H⋯π interaction occurs. In the crystal, molecules are linked into sheets lying parallel to the bc plane by C—H⋯O and C—H⋯N hydrogen bonds. The crystal packing also features weak C—H⋯π interactions.
doi:10.1107/S1600536811048653
PMCID: PMC3239058
PMID: 22199906
In the title compound, [Ni(C17H17FN3O3)2]n, the NiII atom exists in a distorted trans-NiN2O4 octahedral geometry defined by two monodentate N-bonded and two bidentate O,O-bonded 1-cyclopropyl-6-fluoro-4-oxido-7-(1-piperazinyl)-1,4-dihydroquinoline-3-carboxylate (ciprofloxacinium) monoanions. The extended two-dimensional structure is a square grid. The Ni atom lies on a center of inversion.
doi:10.1107/S1600536807065555
PMCID: PMC2915111
PMID: 21200524
In the title compound, C25H21F2N3O5, the pyrimidine and difluorobenzyloxy rings are twisted away from the central quinoline ring system, making dihedral angles of 54.6 (1) and 74.1 (1)°, respectively. A weak C—H⋯O interaction links symmetry-related molecules, forming a pseudo-dimer. π–π interactions between the quinoline rings of symmetry-related molecules [centroid–centroid distance = 3.5479 (10) Å] link these dimers into chains parallel to [101]. Weak C—H⋯π interactions join adjacent chains, forming a two-dimensional layer parallel to (101).
doi:10.1107/S1600536809030499
PMCID: PMC2970014
PMID: 21577516
The asymmetric unit of the title compound, C17H10ClF2N3O, contains three independent molecules. In each molecule, the C=C bond has a cis conformation with respect to the triazole and chlorophenyl groups. The dihedral angles formed by the triazole ring with the diflurophenyl and chlorophenyl benzene rings, respectively, are 20.10 (14) and 73.22 (15), 25.31 (15) and 84.44 (15), and 16.44 (13) and 61.72 (14)° in the three molecules while the dihedral angles between the benzene rings are 66.54 (13), 85.82 (12) and 58.37 (12)°.
doi:10.1107/S1600536812022118
PMCID: PMC3379402
PMID: 22719600
In the title compound, C28H21ClN2O3, the quinoline ring system is essentially planar with a maximum deviation of 0.0436 (17) Å. The isoxazole and cyclohexane rings adopt envelope conformations. The isoxazole ring is almost orthogonal to both the quinoline ring system and the cyclohexane ring, making dihedral angles of 85.75 (8) and 81.46 (9) °, respectively. The O atom deviates signifigantly from the six-membered carbocyclic ring by 0.3947 (16) Å. In the crystal, molecules are linked into inversion dimers via pairs of C—H⋯O interactions, resulting in R
2
2(24) ring motifs.
doi:10.1107/S1600536812042523
PMCID: PMC3515270
PMID: 23284490