The mean planes of the two benzene rings in the title compound, C17H16FNO, are twisted slightly, making a dihedral angle of 7.8 (1)°. The prop-2-en-1-one group is also twisted slightly with a C—C—C—O torsion angle of −11.6 (3)°. In the crystal, weak inter­molecular C—H⋯O inter­actions link pairs of mol­ecules, forming centrosymmetric dimers.

The asymmetric unit of the title compound N,N-dimethyl-2-[(2-methyl­phen­yl)phenyl­meth­oxy]ethanaminium picrate picric acid, C18H24NO+·C6H2N3O7 −·C6H3N3O7, contains one orphenadrinium cation, one picrate anion and one picric acid mol­ecule. In the orphenadrine cation, the two aromatic rings form a dihedral angle of 70.30 (7)°. There is an intra­molecular O—H⋯O hydrogen bond in the picric acid mol­ecule, which generates an S(6) ring motif. In the crystal structure, the orphenadrine cations, picrate anions and picric acid mol­ecules are connected by strong inter­molecular N—H⋯O hydrogen bonds, π⋯π inter­actions between the benzene rings of cations and anions [centroid–centroid distance = 3.5603 (9) Å] and weak C—H⋯O hydrogen bonds, forming a three-dimensional network.

In the crystal structure of the title compound, C23H31N3O2+·2C6H2N3O7 −, {systematic name: 1-[3-(5H-dibenz[b,f]azepin-5-yl)prop­yl]-4-(2-hy­droxy­eth­yl)piperazine-1,4-diium bis­(2,4,6-trinitro­phrenolate)} the piperazine group in the opipramol dication is protonated at both N atoms. Each picrate anion inter­acts with the protonated N atom in the cation through a bifurcated N—H⋯O hydrogen bond, forming an R 2 1(6) ring motif. In the cation, the dihedral angle between the mean planes of the two benzene rings is 50.81 (8) Å. Inter­molecular O—H⋯O and weak C—H⋯O hydrogen bonds, and weak π-ring and π–π stacking inter­actions dominate the crystal packing.

The title compound (systematic name: 4-{3-[2-aza­tricyclo­[9.4.0.03,8]penta­deca-1(15),3,5,7,11,13-hexaen-2-yl]prop­yl}-1-(2-hy­droxy­eth­yl)piperazine-1,4-diium dichloride), C23H31N3O+·2Cl−, is the dihydro­chloride of a piperazine derivative bearing a bulky 3-(5H-dibenz[b,f]azepin-5-yl)propyl substituent. Protonation took place on both N atoms of the piperazine unit. The diaza­cyclo­hexane ring adopts a chair conformation. N—H⋯Cl, O—H⋯Cl and C—H⋯Cl hydrogen bonding as well as C—H⋯O contacts connect the components into a three-dimensional network in the crystal. Two C—H⋯π contacts are also observed.

The title compound, C 22 H 28 F 3 N 3 OS 2? 9 2(C 6 H 2 N 3 O 7 -) 9 (CH 3 ) 2 SO-the picrate salt of the potent antipsychotic drug, fluphenazine-crystallizes in the triclinic P-1 space group with unit cell parameters a = 10.6333(12) Å , b = 11.9696(12) Å , c = 17.7036 (15) Å , a = 103.265(9)°, b = 98.414(9)°, c = 102.702 (10)°. The ionic fragments: the fluphenazinium dictation, and two picrate anions, are joined by means of strong N-HÁÁÁO and weak C-HÁÁÁO hydrogen bonds into the chains of alternating cations and anions, expanding along [010] direction. Within the chain, the picrates interact by means of short pÁÁÁp interactions: the mean distance between the planes is 3.366 Å ; additional interaction of the same type between one of the picrates and the phenyl ring of the phenothiazine ring system additionally strengthen the pattern. The phenothiazine ring exists in a typical, ''butterflylike'' conformation, with two terminal rings planar and the central ring in a slightly flattened boat form. This conformation results in the dihedral angle between the terminal rings of 41.76(5)°. The aliphatic chain which substitutes phenothiazine at N-position is not in an extended conformation, the torsion angles along this chain are 75.95(14)°a nd -163.96(10)°. The structure contains also the solvent-dimethylsulphoxide molecules, which are connected with the cation-anion structure by means of strong O-HÁÁÁO hydrogen bonds.Keywords Fluphenazine Á Phenothiazines Á Picrates Á Hydrogen bonds Á Crystal packing Experimental PreparationFluphenazine dihydrochloride (5.6 g, 0.01 mol) was dissolved in 25 mL of methanol and picric acid (2.4 g, 0.01 mol) was dissolved in 25 mL of methanol. Both the solutions were mixed and the mixture was stirred in a beaker at 333 K for 1 h and was kept aside for 3 days at room temperature. The formed salt was filtered and dried in vaccum desiccator over phosphorous pentoxide. It was observed that, regardless of the proportions in which the donor and acceptor were mixed, only the 1:2 complex was formed. X-ray quality crystals were obtained from a solution of dimethylsulphoxide after slow evaporation (m.p.: 501-503 K). CrystallographyYellow transparent prism-like crystal (0.2, 0.2, 0.08 mm) was used for data collection. Diffraction data were collected at 120(1) K by the x-scan technique up to 2h = 56.5°, on an Xcalibur Eos diffractometer [1] with graphite-monochromatized MoK a radiation (k = 0.71073 Å ). The temperature

Key indicators: single-crystal X-ray study; T = 173 K; mean (C-C) = 0.005 Å; R factor = 0.042; wR factor = 0.103; data-to-parameter ratio = 13.2.The geometric parameters of the title molecule, C 15 H 12 BrN 3 O 4 , are in the usual ranges. The dihedral angle between the two benzene rings is 49.69 (10) . In the crystal structure, molecules are connected by intermolecular N-HÁ Á ÁO hydrogen bonds to form a one-dimensional chain in the c-axis direction. ExperimentalCrystal data C 15 H 12 BrN 3 O 4 M r = 378.19 Monoclinic, P2 1 =c a = 7.2604 (8) Å b = 21.8931 (19) Å c = 9.5795 (12) Å = 97.882 (9) V = 1508.3 (3) Å 3 Z = 4 Mo K radiation = 2.75 mm À1 T = 173 (2) K 0.33 Â 0.32 Â 0.30 mm Data collection Stoe IPDS II two-circle diffractometer Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) T min = 0.414, T max = 0.436 9259 measured reflections 2818 independent reflections 2368 reflections with I > 2(I) R int = 0.060

In the title compound, C16H14O, the asymmetric unit consists of three crystallographically independent mol­ecules. The anthracene units are essentially planar, with maximum deviations of 0.165 (1), 0.153 (1) and 0.045 (1) Å in the three mol­ecules. In the crystal structure, mol­ecules are linked via inter­molecular C—H⋯O hydrogen bonds. Further stabilization is provided by C—H⋯π inter­actions.

In the title compound, C14H14O, the two benzene rings are almost orthogonal [dihedral angle = 87.78 (8) °]. The hy­droxy group lies approximately in the plane of its attached benzene ring [O—C—C—C torsion angle = −17.47 (17)°], and the hydroxyl and methyl groups lie to the same side of the mol­ecule and are gauche to each other. In the crystal, a hexa­meric aggregate mediated by a ring of six O—H⋯O hydrogen bonds occurs, generating an R 6 6(12) loop.