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In the title compound, C20H25NO2, the cyclohexyl ring adopts a slightly disordered chair conformation. The dihedral angle between the mean planes of the quinoline ring and the carboxylate group is 22.2 (6)°. In the crystal, weak C—HN interactions make chains along [010].
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In the title compound, C9H10N4OS, the dihedral angle between the benzene and 1H-1,2,4-triazole-5(4H)-thione rings is 67.51 (16)°. In the crystal, molecules are liked via N—HO hydrogen bonds, forming chains along the c-axis direction. The chains are linked via O—HS hydrogen bonds, forming corrugated layers lying parallel to the bc plane. The layers are linked via N—HN and N—HS hydrogen bonds, forming a three-dimensional network.
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In the title compound, C10H9ClN4S, the dihedral angle between the mean planes of the phenyl and 1H-1,2,4-triazole-5(4H)-thione rings is 25.3 (9)°. The latter ring is essentially planar, with maximum deviations of 0.010 and −0.010 Å for the ring N atom in the 4-position and ring C atom bearing the methyl group, respectively. An intramolecular C—HS contact occurs. In the crystal, pairs of weak N—HS interactions link the molecules into inversion dimers in the ac plane, forming R22(8) graph-set motifs. In addition, weak π–π interactions [centroid–centroid distances = 3.3463 (14) and 3.6127 (13)Å] are observed.
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The title salt, 2C19H23FN3O3+·C2O42− {systematic name: bis-[4-(3-carboxy-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)-1-ethylpiperazin-1-ium] oxalate}, crystallizes with two independent monocations (A and B) and an oxalate dianion (C) in the asymmetric unit. The piperazinium ring in both the cations adopts a slightly disordered chair conformation. The dihedral angles between the mean planes of the cyclopropyl ring and the 10-membered quinoline ring are 50.6 (5)° (A) and 62.2 (5)° (B). In each of the cations, a single O—HO intramolecular hydrogen bond is observed. In the crystal, the oxalate anions interact with the cations through N—HO hydrogen bonds and weak C—HO interactions, forming R22(8) graph-set ring motifs. Weak C—HF interactions along with further C—HO interactions are observed between the cations, forming zigzag chains along [001]. In addition, π–π stacking interactions are observed with centroid–centroid distances of 3.5089 (13), 3.5583 (13), 3.7900 (13) and 3.7991 (13) Å.
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The title salts, C8H13N4+·Cl−, (I), and C8H13N4+·NO3−, (II), contain linked pyridinium–piperazine heterocycles. In the crystal of (I), weak N—HCl interactions lead to zigzag chains along [100] while in the crystal of (II), bifurcated N—H(O,O) hydrogen bonds and weak C—HO interactions collectively link the components into infinite chains along [100].
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In the title salt, C23H26F3N2OS+·C4H5O6− [systematic name: 1-(2-hydroxyethyl)-4-[3-(2-(trifluoromethyl)thioxanthen-9-ylidene)propyl]piperazin-1-ium 3-carboxy-2,3-dihydroxypropionate], the monoprotonated piperazine ring in the cation adopts a chair conformation, while the thiopyran ring of the thioxanthene group has a boat conformation. The dihedral angle between the mean planes of the two outer aromatic rings of the thioxanthene groups is 31.6 (2)°. In the crystal, the cations and anions are linked via O—HO, N—HO, O—HN and C—HO hydrogen bonds, forming chains propagating along [100]. In addition, R22(7), R22(11), R22(10) and R22(12) graph-set ring motifs involving the anions, and R22(9) graph-set ring motifs involving both the cations and anions are observed. The three F atoms of the trifluoromethyl group are disordered over two sets of sites and the individual atoms were refined with occupancy ratios of 0.54 (6):0.46 (6), 0.72 (2):0.28 (2) and 0.67 (3):0.33 (3).
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In the cation of the title salt [systematic name: 4-(2H-1,3-benzodioxol-5-ylmethyl)piperazin-1-ium 2,4,6-trinitrophenolate], C12H17N2O2+·C6H2N3O7−, the piperazine ring adopts a slightly disordered chair conformation. The piperonyl ring system and the piperazine ring are twisted with respect to each other with an N—C—C—C torsion angle of 40.7 (2)°. In the anion, the dihedral angles between the mean planes of the nitro substituents ortho to the phenolate O atom and the mean plane of the phenyl ring are 28.8 (9) and 32.2 (8)°. In contrast, the nitro group in the para position lies much closer to the aromatic ring plane, subtending a dihedral angle of 3.0 (1)°. In the crystal, the cations and anions interact through N—HO hydrogen bonds and a weak C—HO interaction. Weak C—HO interactions are also observed between the anions, forming R22(10) graph-set ring motifs. In addition, a weak centroid–centroid π–π stacking interaction between the aromatic rings of the cation and the anion, with an intercentroid distance of 3.7471 (9) Å, contributes to the crystal packing, resulting in a two-dimensional network along (10-1).
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In the cation of the title salt, C3H6N3+·C4H5O4−, the protonated pyrazolium ring is planar (r.m.s. deviation = 0.012 Å). An intramolecular C—HO hydrogen bond occurs in the anion. In the crystal, N—HO hydrogen bonds and a weak C—HO interaction between the cations and anions form two sets of R22(8) graph-set ring motifs. Intermolecular O—HO hydrogen bonds between these lead to a criss-cross pattern along the b axis. In addition to the classical hydrogen bonds, a weak C—Hπ(pyrazolium) interaction is observed and contributes to crystal packing. All of these interactions link the molecules into a two-dimensional supramolecular framework parallel to (10-1).
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In the title hydrated salt [systematic name: 1-(1,3-benzodioxol-5-ylmethyl)piperazin-1-ium 4-nitrobenzoate monohydrate], C12H17N2O2+·C7H4NO4−·H2O, the piperazinium ring of the cation adopts a slightly distorted chair conformation. The piperonyl and piperazine rings are rotated with respect to each other with an N—C—C—C torsion angle of 45.6 (2)°. In the anion, the nitro group is almost coplanar with the adjacent benzene ring, forming a dihedral angle of only 3.9 (4)°. In the crystal, the cations, anions and water molecules are linked through N—HO and O—HO hydrogen bonds into chains along the a axis. In addition, weaker intermolecular C—HO interactions are also observed within the chains. The anions form centrosymmetric couples through π-stacking interactions, with an intercentroid distance of 3.681 (4) Å between the benzene rings.
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In the title salt {systematic name: 1-[(1,3-benzodioxol-5-yl)methyl]piperazin-1-ium 4-chlorobenzoate}, C12H17N2O2+·C7H4ClO2−, the piperazine ring adopts a slightly disordered chair conformation. The dioxole ring is in a flattened envelope conformation with the methylene C atom forming the flap. The relative orientation of the piperonyl ring system and the piperazine rings is reflected in the N—C—CC torsion angle of 132.3 (1)°. In the anion, the mean plane of the carboxylate group is twisted from that of the benzene ring by 14.8 (9)°. In the crystal, the components are linked by N—HO and weak C—HO hydrogen bonds, forming chains along [010].
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In the title salt, C6H12N3+·C7H3N2O7−, the imidazole ring is planar, with a maximum deviation of 0.0013 (14) Å for the N attached to the propanaminium group. In the anion, a single intramolecular O—HO hydrogen bond is observed. The mean planes of the nitro groups in the anion are twisted from the benzene ring mean plane making dihedral angles of 24.7 (9) and 3.9 (6)°. In the crystal, the ammonium H atoms form N—HN and N—HO hydrogen bonds, resulting in an infinite chain along [111]. In addition to the classical hydrogen bonds, weak C—HO and π–π [centroid–centroid distance = 3.7124 (9) Å] interactions are also observed, which lead to the formation a three-dimensional supramolecular structure that links the chains into layers along the bc plane.
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The title salt, C9H8FN2+·C2F3O2−, crystallizes with two independent cations (A and B) and two independent anions (C and D) in the asymmetric unit. In the cations, the dihedral angles between the benzene and pyrazolium rings are 23.7 (3)° in cation A and 1.8 (8)° in cation B. In the crystal, each anion links to the two cations via N—HO hydrogen bonds, forming a U-shaped unit with an R44(14) ring motif. These U-shaped units stack along the a axis and are linked via C—HO and C—HF hydrogen bonds, forming slabs lying parallel to (100). Within the slabs there are π–π interactions between the pyrazolium rings [inter-centroid distance = 3.6326 (15) Å] and between the benzene rings [inter-centroid distance = 3.7244 (16) Å]. In the anions, the F atoms of the trifluoromethyl groups are disordered over two sets of sites, with refined occupancy ratios of 0.58 (3):0.42, 0.540 (14):0.46 (14), and 0.55 (2):0.45 (2) for anion C, and 0.73 (5):0.27 (5), 0.63 (5):0.37 (5), and 0.57 (8):0.43 (8) for anion D.
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In the title compound, C15H17N3OS, the dihedral angle between the mean planes of the 2-hydroxynapthyl ring system and the hydrazinecarbothioamide group is 73.7 (3)°. In the crystal, weak O—HS and C—HO interactions and π–π stacking interactions involving one of the hydroxynapthyl rings with a centroid–centroid distance of 3.6648 (14) Å are observed, forming infinite chains along [010]. In addition, N—HS interactions occur.
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The title compound, C12H17N3OS, crystallizes with two independent molecules (A and B) in the asymmetric unit. The dihedral angle between the mean planes of the benzene ring and the hydrazinecarbothioamide group are 6.9 (4) and 37.2 (5)° in molecules A and B, respectively. An intramolecular O—HN hydrogen bond is observed in each molecule. This serves to maintain an approximately planar conformation for molecule A, but leaves a significant twist between these two groups in molecule B. In the crystal, a weak N—HS interaction is observed, forming inversion dimers among the B molecules and resulting in an R22(8) motif. These dimers are further interconnected by weak N—HO and C—HO intermolecular interactions, forming chains along [011].
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The title co-crystal, 3-(4-fluorophenyl)-1H-pyrazole–5-(4-fluorophenyl)-1H-pyrazole (1/1), C9H7FN2, crystallizes with four independent molecules (A, B, C and D) in the asymmetric unit exhibiting two tautomeric forms (A and D; B and C) due to N—H proton exchange between the two N atoms of the pyrazole ring. The dihedral angles between the mean planes of the pyrazole and benzene rings are 15.6 (1), 19.8 (9), 14.0 (1) and 10.7 (7)° in molecules A, B, C and D, respectively. In the crystal, N—HN hydrogen bonds link the four molecules in the asymmetric unit into a ring with an R44(12) motif. Furthermore, weak C—HF interactions link the molecules into a three-dimensional network.
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The title compound, C12H18N4O2, crystallizes in the zwitterionic form with protonation at the N atom of the piperazine ring bearing the carboxylate group. The piperazine ring adopts a slightly distorted chair conformation. In the crystal, N—HO hydrogen bonds are observed, forming chains along [010]. The packing is consolidated by C—HO interactions, which generate a three-dimensional network.
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The title salt {systematic name: bis[1-(3-chlorophenyl)piperazinium 2,4,6-trinitrophenolate]–picric acid (2/1)}, 2C10H14ClN2+·2C6H5N3O7−·C6H6N3O7, crystallized with two independent 1-(3-chlorophenyl)piperazinium cations, two picrate anions and a picric acid molecule in the asymmetric unit. The six-membered piperazine ring in each cation adopts a slightly distorted chair conformation and contains a protonated N atom. In the picric acid molecule, the mean planes of the nitro groups in the ortho-, meta-, and para-positions are twisted from the benzene ring by 31.5 (3), 7.7 (1), and 3.8 (2)°, respectively. In the anions, the dihedral angles between the benzene ring and the ortho-, meta-, and para-nitro groups are 36.7 (1), 5.0 (6), 4.8 (2)°, and 34.4 (9), 15.3 (8), 4.5 (1)°, respectively. The nitro group in one anion is disordered and was modeled with two sites for one O atom with an occupancy ratio of 0.627 (7):0.373 (7). In the crystal, the picric acid molecule interacts with the picrate anion through a trifurcated O—HO four-centre hydrogen bond involving an intramolecular O—HO hydrogen bond and a weak C—HO interaction. Weak intermolecular C—HO interactions are responsible for the formation of cation–anion–cation trimers resulting in a chain along [010]. In addition, weak C—HCl and weak π–π interactions [centroid–centroid distances of 3.532 (3), 3.756 (4) and 3.705 (3) Å] are observed and contribute to the stability of the crystal packing.