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1.  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.
doi:10.1107/S1600536811011615
PMCID: PMC3089319  PMID: 21754278
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].
doi:10.1107/S1600536808034715
PMCID: PMC2959496  PMID: 21581071
3.  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.
doi:10.1107/S1600536811028170
PMCID: PMC3213526  PMID: 22091105
4.  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.
doi:10.1107/S160053681104757X
PMCID: PMC3239011  PMID: 22199860
5.  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)°.
doi:10.1107/S1600536812028711
PMCID: PMC3394047  PMID: 22798912
6.  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.
doi:10.1107/S1600536812020831
PMCID: PMC3379295  PMID: 22719493
7.  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.
doi:10.1107/S1600536812001249
PMCID: PMC3275192  PMID: 22347048
8.  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.
doi:10.1107/S160053681004328X
PMCID: PMC3009166  PMID: 21588904
9.  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.
doi:10.1107/S1600536809029729
PMCID: PMC2977261  PMID: 21583715
10.  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.
doi:10.1107/S1600536809045425
PMCID: PMC2972051  PMID: 21578727
11.  Ethyl 4-oxo-8-trifluoro­methyl-1,4-dihydro­quinoline-3-carboxyl­ate 
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
12.  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.
doi:10.1107/S1600536807060825
PMCID: PMC2914913  PMID: 21200557
13.  (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.
doi:10.1107/S1600536808034818
PMCID: PMC2959890  PMID: 21581235
14.  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.
doi:10.1107/S160053681203632X
PMCID: PMC3435823  PMID: 22969669
15.  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.
doi:10.1107/S1600536814001548
PMCID: PMC3998350  PMID: 24764911
16.  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.
doi:10.1107/S1600536807068298
PMCID: PMC2960459  PMID: 21201277
17.  Tetra­aqua­bis(2-oxo-1,2-dihydro­quinoline-4-carboxyl­ato-κO 4)nickel(II) 
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
18.  (1R*,3′S*,4′R*)-4′-(4-Chloro­phen­yl)-3′-[(4-hy­droxy-2-oxo-1,2-dihydro­quinolin-3-yl)carbon­yl]-1′-methyl­spiro­[ace­naphthyl­ene-1,2′-pyrrolidin]-2-one 
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
19.  6-(2-Chloro­benz­yl)-1-(4-chloro­phen­yl)-7-hy­droxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one 
The title compound, C19H15Cl2N3O2, was obtained by a one-step cyclo­condensation of 2-amino-1-(4-chloro­phen­yl)imidazoline with diethyl (2-chloro­benz­yl)malonate under basic conditions. In the crystalline state, the mol­ecule exists as the 7-hy­droxy-5-oxo tautomer. The dihedral angles between the fused imidazopyrimidine and aromatic chloro­phenyl and chloro­benzyl rings are 14.2 (1) and 70.7 (1)°, respectively. The conformation of the mol­ecule is influenced by the intra­molecular C—H⋯O and C—H⋯N hydrogen bonds, giving a nearly planar five-ring fused system [maximum deviation from the mean plane = 0.296 (2) Å]. In the crystal structure, strong inter­molecular O—H⋯O hydrogen bonds link the mol­ecules into chains along the c axis. These chains are further stabilized by weak C—H⋯Cl and π–π inter­actions [centroid–centroid distance = 3.6707 (12) Å].
doi:10.1107/S160053681003919X
PMCID: PMC3009369  PMID: 21588948
20.  2-(4-Methyl­phen­yl)-1-phenyl­sulfonyl-3-nitro-1,2-dihydro­quinoline 
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
21.  2-Amino-4-(4-chloro­phen­yl)-5,6-dihydro­benzo[h]quinoline-3-carbonitrile–3-amino-1-(4-chloro­phen­yl)-9,10-dihydro­phenanthrene-2,4-dicarbonitrile (1/4) 
The asymmetric unit of the 1:4 title co-crystal of 2-amino-4-(4-chloro­phen­yl)-5,6-dihydro­benzo[h]quinoline-3-carbonitrile and 3-amino-1-(4-chloro­phen­yl)-9,10-dihydro­phenanthrene-2,4-dicarbonitrile, 0.2C20H14ClN3·0.8C22H14ClN3, has the atoms of the fused-ring system and those of the amino, cyano and chloro­phenyl substitutents overlapped. The fused-ring system is buckled owing to the ethyl­ene linkage in the central ring. There are two independent overlapped mol­ecules in the asymmetric unit. In one independent mol­ecule, the two flanking aromatic rings are twisted by 24.4 (1)° and the ring of the chloro­phenyl substituent is twisted by 87.3 (1)° relative to the amino- and cyano-bearing aromatic ring. In the second mol­ecule, the respective dihedral angles are 26.1 (1) and 57.8 (1)°. The two independent mol­ecules are linked by N—H⋯N hydrogen bonds into dimers.
doi:10.1107/S1600536811040529
PMCID: PMC3247609  PMID: 22219914
22.  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.
doi:10.1107/S160053681303448X
PMCID: PMC3998275  PMID: 24764836
23.  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.
doi:10.1107/S1600536814006059
PMCID: PMC3998605  PMID: 24826167
24.  (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)°.
doi:10.1107/S1600536812022118
PMCID: PMC3379402  PMID: 22719600
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)°.
doi:10.1107/S160053681301965X
PMCID: PMC3793697  PMID: 24109284

Results 1-25 (190088)