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1.  2-(2-Chloro-6,7-dimethyl­quinolin-3-yl)-2,3-dihydro­quinolin-4(1H)-one 
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.
PMCID: PMC3213526  PMID: 22091105
2.  Ethyl 1-cyclo­propyl-6,7-difluoro-8-meth­oxy-4-oxo-1,4-dihydro­quinoline-3-carboxyl­ate 
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].
PMCID: PMC2959496  PMID: 21581071
3.  Bis(2-carboxybenzo­ato-κO 1)bis­[1-cyclo­propyl-6-fluoro-4-oxo-7-(piperazin-4-ium-1-yl)-1,4-dihydro­quinoline-3-carboxyl­ato-κ2 O 3,O 4]manganese(II) dihydrate 
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.
PMCID: PMC3089319  PMID: 21754278
4.  7-{4-[(1,3-Benzodioxol-5-yl)meth­yl]piperazin-1-yl}-1-cyclo­propyl-6-fluoro-4-oxo-1,4-dihydro­quinoline-3-carb­oxy­lic acid 
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)°.
PMCID: PMC3394047  PMID: 22798912
5.  Bis[(2R,6S)-4-(5-amino-3-carb­oxy-1-cyclo­propyl-6,8-difluoro-4-oxo-1,4-dihydro­quinolin-7-yl)-2,6-dimethyl­piperazin-1-ium] sulfate penta­hydrate 
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.
PMCID: PMC3239011  PMID: 22199860
6.  Ethyl 6-chloro-2-oxo-4-phenyl-1,2-dihydro­quinoline-3-carboxyl­ate 
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.
PMCID: PMC2972051  PMID: 21578727
7.  1-Cyclo­propyl-6-fluoro-7-(4-nitro­so­piperazin-1-yl)-4-oxo-1,4-dihydro­quinoline-3-carboxylic acid 
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.
PMCID: PMC2977261  PMID: 21583715
8.  (Z)-Ethyl 3-(4-chloro­phen­yl)-2-cyano-3-(2,6-difluoro­benzamido)acrylate 
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.
PMCID: PMC2959890  PMID: 21581235
9.  2-(4-Chloro­phen­yl)-2,3-di­hydro­quinolin-4(1H)-one 
The title mol­ecule, C15H12ClNO, features a di­hydro­quinolin-4(1H)-one moiety attached to a chloro­benzene ring. The heterocyclic ring has a half-chair conformation with the methine C atom lying 0.574 (3) Å above the plane of the five remaining atoms (r.m.s. deviation = 0.0240 Å). The dihedral angles between the terminal benzene rings is 77.53 (9)°, indicating a significant twist in the mol­ecule. In the crystal, supra­molecular zigzag chains along the c-axis direction are sustained by N—H⋯O hydrogen bonds. These are connected into double chains by C—H⋯π inter­actions.
PMCID: PMC3998350  PMID: 24764911
10.  Poly[[[[1-ethyl-6,8-difluoro-7-(3-methyl­piperazin-1-yl)-4-oxo-1,4-dihydro­quinoline-3-carboxyl­ato]cadmium]-μ-benzene-1,4-dicarboxyl­ato] trihydrate] 
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.
PMCID: PMC3009166  PMID: 21588904
11.  Ethyl 1-(2,4-dichloro­benz­yl)-4-oxo-7-trifluoro­meth­yl-1,4-dihydro­quinoline-3-carboxyl­ate 
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.
PMCID: PMC3275192  PMID: 22347048
12.  rac-2-(2-Chloro-6-methyl­quinolin-3-yl)-2,3-dihydro­quinolin-4(1H)-one 
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.
PMCID: PMC3379295  PMID: 22719493
13.  Moxifloxacinium chloride monohydrate 
The title compound {systematic name: 7-[(1S,6S)-8-aza-2-azonia­bicyclo­[4.3.0]non-8-yl]-1-cyclo­propyl-6-fluoro-8-meth­oxy-4-oxo-1,4-dihydro­quinoline-3-carb­oxy­lic acid chloride monohydrate}, C21H25FN3O4 +·Cl−·H2O, crystallizes with two moxi­floxa­cinium cations, two chloride ions and two uncoordinated water mol­ecules in the unit cell. The crystal structure has a pseudo-inversion center except for the chloride ions. In both moxi­floxa­cinium cations, the quinoline rings are approximately planar, the maximum atomic deviations being 0.107 (3) and 0.118 (3) Å. The piperidine rings adopt a chair conformation while the pyrrolidine rings display a half-chair conformation. In the crystal, the carboxyl groups, the protonated piperidyl groups, the uncoordinated water mol­ecule and chloride anions participate in O—H⋯O, O—H⋯Cl and N—H⋯Cl hydrogen bonding; weak inter­molecular C—H⋯O and C—H⋯Cl hydrogen bonding is also present in the crystal structure.
PMCID: PMC3201314  PMID: 22058817
14.  8-{1-[(4′-Fluoro-[1,1′-biphen­yl]-4-yl)meth­yl]piperidin-4-yl}-3,4-di­hydro­quinolin-2(1H)-one chloro­form 0.25-solvate 
In the asymmetric unit of the title compound, C27H27FN2O·0.25CHCl3, there are two independent mol­ecules (A and B) together with a partially disordered chloro­form mol­ecule situated about an inversion center. The conformation of the two mol­ecules is very similar. The bridging piperidine rings each have a chair conformation while the piperidin-2-one rings of the quinoline moiety have screw-boat conformations. The benzene rings of the biphenyl moiety are inclined to one another by 26.37 (4) and 23.75 (15)° in mol­ecules A and B, respectively. The mean plane of the central piperidine ring [r.m.s. deviation = 0.241 (2) Å in both mol­ecules A and B] is inclined to the benzene ring of the quinoline moiety by 80.06 (4) in A and 83.75 (15)° in B, while it is inclined to the adjacent benzene ring of the biphenyl group by 73.623 (15) in A and 75.65 (14)° in B. In the crystal, individual mol­ecules are linked by pairs of N—H⋯O hydrogen bonds, forming A–A and B–B inversion dimers with R 2 2(8) ring motifs. The dimers are stabilized by C—H⋯O hydrogen bonds and linked via C—H⋯F and C—H⋯N hydrogen bonds into a three-dimensional network. Several C—H⋯π inter­actions are also present.
PMCID: PMC3998275  PMID: 24764836
15.  Poly[[[(1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro­quinoline-3-carboxyl­ato)manganese(II)]-μ3-4,4′-oxydibenzoato] monohydrate] 
In the title compound, {[Mn(C16H18N3O3)(C14H8O5)]·H2O}n, the unique MnII ion is coordinated by two O atoms from a chelating 1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro­quinoline-3-carboxyl­ate ligand and three O atoms from three 4,4′-oxydibenzoate ligands, forming a distorted square-pyramidal coordination environment. In the crystal structure, centrosymmetric dinuclear manganese units are linked via 4,4′-oxydibenzoate ligands into one-dimensional chains; these chains are, in turn, connected via inter­molecular N—H⋯O and O—H⋯O hydrogen bonds to form a two-dimensional supra­molecular network. The O atom of the solvent water mol­ecule is disordered over two sites with equal occupancies; the attached H atoms are common to both sites.
PMCID: PMC2914913  PMID: 21200557
16.  7-[(7S)-7-Aza­niumyl-5-aza­spiro­[2.4]hept-5-yl]-8-chloro-6-fluoro-1-[(1S,2R)-2-fluoro­cyclo­prop­yl]-4-oxo-1,4-dihydroquinoline-3-carboxyl­ate methanol monosolvate 
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.
PMCID: PMC3435823  PMID: 22969669
17.  (Z)-3-(4-Chloro­phen­yl)-1-(2,4-difluoro­phen­yl)-2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-one 
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)°.
PMCID: PMC3379402  PMID: 22719600
18.  (4-Chloro-2-fluoro­phen­yl)[1-(2,6-difluoro­phen­yl)but-3-en­yl]amine 
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.
PMCID: PMC2977711  PMID: 21583847
19.  Enrofloxacin hydro­chloride dihydrate 
The asymmetric unit of the title compound, C19H23FN3O3 +·Cl−·2H2O [systematic name: 4-(3-carb­oxy-1-cyclo­propyl-6-fluoro-4-oxo-1,4-di­hydro­quin­o­lin-7-yl)-1-ethyl­piperazin-1-ium chloride dihydrate], consists of two independent monocations of the protonated enrofloxacin, two chloride anions and four water mol­ecules. In the cations, the piperazinium rings adopt chair conformations and the dihedral angles between the cyclo­propyl ring and the 10-membered quinoline ring system are 56.55 (2) and 51.11 (2)°. An intra­molecular O—H⋯O hydrogen bond is observed in each cation. In the crystal, the components are connected via O—H⋯Cl, N—H⋯Cl and O—H⋯O hydrogen bonds, and a π–π inter­action between the benzene rings [centroid–centroid distance = 3.6726 (13) Å], resulting in a three-dimensional array.
PMCID: PMC3998605  PMID: 24826167
20.  1-(4-Chloro-2-fluoro-5-nitro­phen­yl)-4-difluoro­methyl-3-methyl-1H-1,2,4-triazol-5(4H)-one 
In the title compound, C10H6ClF3N4O3, the dihedral angle between the benzene ring and the triazolone ring is 59.9 (1)°, while the nitro substituent subtends an angle of 39.5 (1)° to the benzene ring plane. In the crystal, pairs of mol­ecules form inversion dimers via C—H⋯O hydrogen bonds.
PMCID: PMC3344505  PMID: 22590267
21.  Aqua­bis[1-ethyl-6-fluoro-7-(4-methyl­piperazin-1-yl)-4-oxo-1,4-dihydro­quinoline-3-carboxyl­ato]zinc(II) dihydrate 
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.
PMCID: PMC2960459  PMID: 21201277
22.  4-(3-Chloro­phen­yl)-3-[(2,6-difluoro­benz­yl)sulfan­yl]-5-(3,4,5-trimeth­oxy­phen­yl)-4H-1,2,4-triazole 
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.
PMCID: PMC3239058  PMID: 22199906
23.  1-(4-Chloro-2-fluoro­phen­yl)-4-difluoro­methyl-3-methyl-1H-1,2,4-triazol-5(4H)-one 
In the crystal structure of the title compound, C10H7ClF3N3O, pairs of mol­ecules are connected into dimers via pairs of C—H⋯O hydrogen bonds. The dihedral angle between the benzene ring and attached triazolone ring is 53.2 (1)°.
PMCID: PMC3344009  PMID: 22589918
24.  N-(5-Chloro-1,3-thia­zol-2-yl)-2,4-difluoro­benzamide 
The title compound, C10H5ClF2N2OS, was obtained by linking an amino heterocycle and a substituted benzoyl chloride. The dihedral angle between the two rings is 41.2 (2)° and the equalization of the amide C—N bond lengths reveals the existence of conjugation between the benzene ring and the thia­zole unit. In the crystal, pairs of N—H⋯N hydrogen bonds link mol­ecules into inversion dimers. Non-classical C—H⋯F and C—H⋯O hydrogen bonds stabilize the crystal structure.
PMCID: PMC3379424  PMID: 22719622
25.  catena-Poly[[aqua­bis­(3-chloro­benzoato-κ2 O,O′)cadmium]-μ-N,N-di­ethyl­nico­tin­amide-κ2 N 1:O] 
In the crystal of the title CdII polymeric complex, [Cd(C7H4ClO2)2(C10H14N2O)(H2O)]n, the CdII cation is chelated by two chloro­benzoate anions and coordinated by two N,N-di­­ethyl­nicotinamide (DENA) ligands and one water mol­ecule in a distorted NO6 penta­gonal–bipyramidal geometry. The CdII cations are bridged by the pyridine N atom and carbonyl O atom of the DENA ligand to form a polymeric chain running along the b axis. Inter­molecular O—H⋯O hydrogen bonds between coordinating water mol­ecules and carboxyl­ate groups link adjacent chains into layers parallel to the bc plane. π–π contacts between benzene rings [shortest centroid–centroid distance = 3.912 (2) Å] further stabilizes the crystal structure. In the mol­ecule, weak C—H⋯O hydrogen bonds occur between the pyridine ring and carboxyl­ate groups; the dihedral angles between the carboxyl­ate groups and adjacent benzene rings are 4.6 (3) and 12.8 (3)°, while the benzene rings are oriented at a dihedral angle of 1.89 (13)°.
PMCID: PMC3793697  PMID: 24109284

Results 1-25 (155194)