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In the title compouund, C15H10F2O, the mol­ecule exists in an E conformation with respect to the C=C bond [1.3382 (16) Å]. The dihedral angle between the fluoro-substituted benzene rings is 6.80 (6)° and the whole mol­ecule is roughly planar (r.m.s. deviation for the non-H atoms = 0.069 Å). In the crystal, mol­ecules are linked by C—H...F and C—H...O inter­actions into sheets lying parallel to the bc plane.

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The asymmetric unit of the title compound, C22H22O4, consists of two independent mol­ecules (A and B). The cyclo­hexene rings adopt slightly distorted sofa conformations in both mol­ecules. The dihedral angles between the benzene rings are 74.16 (13) and 71.85 (13)° in mol­ecules A and B, respectively. In the crystal, weak C—H...O hydrogen bonds link the mol­ecules into a ribbon-like structure along the b axis. Weak C—H...π inter­actions are also observed.

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The anion of the title salt, C6H9N2+·C6H4NO3, undergoes an enol-to-keto tautomerism during the crystallization. In the crystal structure, the cation and anion are held together by a relatively short N—H...O hydrogen bond, and the two anions are further connected to each other by a pair of N—H...O hydrogen bonds with an R22(8) ring motif, thus forming a centrosymmetric 2 + 2 aggregate. The aggregates are further linked through weak N—H...O and C—H...O hydrogen bonds, resulting a three-dimensional network.

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The 3-chloro­benzoate anion of the title salt, C6H9N2+·C7H4ClO2, is nearly planar with a dihedral angle of 2.44 (13)° between the benzene ring and the carboxyl­ate group. In the crystal, the protonated N atom and the 2-amino group of the cation are hydrogen bonded to the carboxyl­ate O atoms of the anion via a pair of N—H...O hydrogen bonds with an R22(8) ring motif, forming an approximately planar ion pair with a dihedral angle of 7.92 (5)° between the pyridinium and benzene rings. The ion pairs are further connected via N—H...O and C—H...O hydrogen bonds, forming a two-dimensional network parallel to the bc plane.

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In the 2-amino­benzoate anion of the title salt, C6H9N2+·C7H6NO2, an intra­molecular N—H...O hydrogen bond is observed. The dihedral angle between the ring and the CO2 group is 8.41 (13)°. In the crystal, the protonated N atom and the 2-amino group of the cation are hydrogen bonded to the carboxyl­ate O atoms via a pair of N—H...O hydrogen bonds, forming an R22(8) ring motif. The ion pairs are further connected via N—H...O hydrogen bonds, resulting in a donor–donor–acceptor–acceptor (DDAA) array of quadruple hydrogen bonds. The crystal structure also features a weak N—H...O hydrogen bond and a C—H...π inter­action, resulting in a three-dimensional network.

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In the title salt, C6H9N2+·C2F3O2, the F atoms of the anion are disordered over two sets of sites, with refined occupancies in a ratio of 0.505 (17):0.495 (17). In the crystal, cations and anions are linked via N—H...O hydrogen bonds, forming R22(8) ring motifs. The ionic units are linked into a two-dimensional network parallel to (100) by N—H...O and weak C—H...O hydrogen bonds. The crystal structure is further stabilized by weak C—H...F hydrogen bonds, resulting in a three-dimensional network.

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In the title salt, 2C4H6ClN4+·C4H2O42−, the complete fumarate dianion is generated by crystallographic inversion symmetry. The cation is essentially planar, with a maximum deviation of 0.018 (1) Å. In the anion, the carboxyl­ate group is twisted slightly away from the attached plane, the dihedral angle between the carboxyl­ate and (E)-but-2-ene planes being 12.78 (13)°. In the crystal, the protonated N atom and the 2-amino group of the cation are hydrogen bonded to the carboxyl­ate O atoms of the anion via a pair of N—H...O hydrogen bonds, forming an R22(8) ring motif. In addition, another type of R22(8) motif is formed by centrosymmetrically related pyrimidinium cations via N—H...N hydrogen bonds. These two combined motifs form a heterotetra­mer. The crystal structure is further stabilized by stong N—H...O, N—H...Cl and weak C—H...O hydrogen bonds, resulting a three-dimensional network.

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The base mol­ecule of the title co-crystal, C7H10N2O2S·C7H6O3, is essentially planar, with a maximum deviation of 0.0806 (14) Å for all non-H atoms. The acid mol­ecule is also nearly planar, with a dihedral angle of 8.12 (14)° between the benzene ring and the carb­oxy group. In the crystal, the acid mol­ecules form an inversion dimer through a pair of O—H...O hydrogen bonds with an R22(8) ring motif. The pyrimidine mol­ecules are linked on both sides of the dimer into a heterotetra­mer via O—H...N and C—H...O hydrogen bonds with R22(8) ring motifs. The heterotetra­mers are further linked by weak C—H...O hydrogen bonds, forming a tape structure along [1-10].
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