Diphenyl-methyl benzoate.

In the title mol-ecule, C20H16O2, the dihedral angle between the phenyl rings of the diphenyl-methyl group is 68.3 (2)°. The benzoate group is essentially planar, with a maximum deviation of 0.017 (2) Šfor the carbonyl O atom, and the two phenyl rings are twisted by 27.5 (4) and 85.6 (9)° from this plane. In the crystal, weak C-H⋯O hydrogen bonds link mol-ecules along [100].

3,3-Dimethyl-2-benzofuran-1(3H)-one.

In the title compound, C(10)H(10)O(2), all the non-H atoms except the methyl C atoms lie on a crystallographic mirror plane. In the crystal, C-H⋯O hydrogen bonds link the mol-ecules into zigzag chains running parallel to [100]. Weak π-π stacking inter-actions between the benzene rings [centroid-centroid distance = 3.9817 (5) Å] link the chains in the [010] direction.

Cyclo-benzaprinium salicylate.

In the title mol-ecular salt [systematic name: 3-(5H-di-benzo[a,d]cyclo-hepten-5-yl-idene)-N,N-dimethyl-1-propanaminium 2-hy-droxy-benzoate], C(20)H(22)N(+)·C(7)H(5)O(3) (-), the benzene rings of the cyclo-benzaprinium cation are inclined with a dihedral angle of 61.66 (7)°. An intra-molecular O-H⋯O hydrogen bond occurs within the salicylate anion, generating an S(6) ring. In the crystal, the cation and anion are linked by an N-H⋯O inter-action.

Opipramol.

IN THE TITLE COMPOUND (SYSTEMATIC NAME: 2-{4-[3-(5H-dibenz[b,f]azepin-5-yl)prop-yl]piperazin-1-yl}ethanol), C(23)H(29)N(3)O, the 5H-dibenz[b,f]azepine and piperazine rings adopt boat and chair conformations, respectively, and the overall shape of the fused ring part of the molecule is a butterfly. In the crystal, O-H⋯N and C-H⋯O hydrogen bonds link the mol-ecules into a layer parallel to the bc plane.

2-(4-Methyl-phen-yl)benzonitrile.

In the title compound, C(14)H(11)N, the dihedral angle between the mean planes of the two benzene rings is 44.6 (7)°. The crystal packing is stabilized by weak inter-molecular π-π stacking inter-actions, the centroid-centroid distances being 3.8172 (12) and 3.9349 (12) Å.

1-(5,5-Dioxido-10H-phenothia-zin-10-yl)ethanone.

In the title compound, C(14)H(11)NO(3)S, the six-membered thia-zine ring fused to two benzene rings adopts a distorted boat conformation. The dihedral angle between the mean planes of the two benzene rings is 45.8 (1)°. The crystal packing is stabilized by weak inter-molecular C-H⋯O inter-actions.

Melitracenium chloride.

IN THE TITLE COMPOUND [SYSTEMATIC NAME: 3-(10,10-dimethyl-anthracen-9-yl-idene)-N,N,N-trimethyl-propanaminium chlor-ide], C(21)H(26)N(+)·Cl(-), the cyclo-hexane ring adopts a chair conformation. The dihedral angle between the terminal benzene rings is 40.43 (12)°. In the crystal, ions are linked through inter-molecular N-H⋯Cl and C-H⋯Cl hydrogen bonds, forming supra-molecular layers parallel to the bc plane.

2,2-Diphenyl-4-(piperidin-1-yl)butanamide.

In the title compound, C(21)H(26)N(2)O, the dihedral angle between the mean planes of the two benzene rings is 81.1 (9)°. The piperidine ring is in a chair conformation. The crystal packing is stabilized by N-H⋯N and N-H⋯O hydrogen bonds and weak inter-molecular C-H⋯O inter-actions.

Cyclo-benzaprinium chloride.

In the title mol-ecular salt [systematic name: 3-(5H-dibenzo[a,d]cyclo-hepten-5-yl-idene)-N,N-dimethyl-propan-aminium chloride], C(20)H(22)N(+)·Cl(-), two cation-anion pairs make up the asymmetric unit. The dihedral angles between the mean planes of the two fused benzene rings of the cation are 49.5 (1) and 50.9 (1)°. The cystal packing is stabilized by N-H⋯Cl hydrogen bonds and weak C-H⋯Cl inter-actions.

Oxomemazine hydro-chloride.

IN THE TITLE COMPOUND [SYSTEMATIC NAME: 3-(5,5-dioxo-phen-othia-zin-10-yl)-N,N,2-trimethyl-propanaminium chloride], C(18)H(23)N(2)O(2)S(+)·Cl(-), the dihedral angle between the two outer aromatic rings of the phenothia-zine unit is 30.5 (2)°. In the crystal, the components are linked by N-H⋯Cl and C-H⋯Cl hydrogen bonds and C-H⋯π inter-actions.

9-[3-(Dimethyl-amino)-prop-yl]-2-trifluoro-meth-yl-9H-thioxanthen-9-ol.

In the title compound, C(19)H(20)F(3)NOS, the dihedral angle between the mean planes of the two benzene rings attached to the thioxanthene ring is 41.8 (7)°; the latter has a slightly distorted boat conformation. The F atoms are disordered over three sets of sites [occupancy ratio = 0.564 (10):0.287 (10):0.148 (5)] and the methyl groups are disordered over two sets of sites [occupancy ratio = 0.72 (4):0.28 (4)]. The crystal packing is stabilized by O-H⋯N and C-H⋯S hydrogen bonds and weak C-H⋯Cg inter-actions.

2,2-Diphenyl-acetamide.

In the title compound, C(14)H(13)NO, which has two mol-ecules in the asymmetric unit, the dihedral angles between the mean planes of the benzene rings are 84.6 (7) and 85.0 (6)°. N-H⋯O hydrogen bonds [forming R(2) (2)(8) ring motifs] and C-H⋯O hydrogen bonds dominate the crystal packing, forming zigzag chains parallel to the a axis. In addition, weak inter-molecular C-H⋯π inter-actions are observed.

Methyl 2-(4-hy-droxy-benzo-yl)benzoate.

In the title compound, C(15)H(12)O(4), the dihedral angle between the benzene rings is 64.0 (6)°. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds, forming C(8) chains propagating in [10[Formula: see text]] and the packing is reinforced by weak C-H⋯O inter-actions.

1-(2-Hy-droxy-eth-yl)-4-{3-[(E)-2-(trifluoro-meth-yl)-9H-thioxanthen-9-yl-idene]prop-yl}piperazine-1,4-diium bis-(3-carb-oxy-prop-2-enoate).

In the title salt, C(23)H(27)F(3)N(2)OS(+)·2C(4)H(3)O(4) (-), a non-merohedral twin [ratio of the twin components = 0.402 (1):0.598 (1)], the -CF(3) group is disordered over two sets of sites with occupancy factors in the ratio 0.873 (2):0.127 (2). The dihedral angle between the two outer aromatic rings of the 9H-thioxanthene unit, whose thio-pyran ring has a screw-boat conformation, is 33.01 (9)°. The diprotonated piperazine ring adopts a chair conformation. In the crystal, inter-molecular O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds between neighboring mol-ecules form zigzag chains along the a axis and contribute to the stabilization of the packing.

1-(2-Hy-droxy-eth-yl)-4-[3-(2-trifluoro-methyl-9H-thioxanthen-9-yl-idene)prop-yl]piperazine-1,4-diium dichloride: the dihydro-chloride salt of flupentixol.

In the title compound, C(23)H(27)F(3)N(2)OS(+)·2Cl(-), the piperazinediium ring adopts a chair conformation. The dihedral angle between the two outer aromatic rings of the 9H-thioxanthene unit is 40.35 (18)°. The F atoms in the trifluoro-methyl group are disordered over two sets of sites with occupancies of 0.803 (6) and 0.197 (6). In the crystal, mol-ecules are connected by N-H⋯Cl, O-H⋯Cl C-H⋯O and C-H⋯Cl hydrogen bonds, forming chains propagating along [001]. There are also C-H⋯π inter-actions present in the crystal structure.

Opipramolium fumarate.

In the crystal structure of the title salt {systematic name: 4-[3-(5H-dibenz[b,f]azepin-5-yl)prop-yl]-1-(2-hy-droxy-eth-yl)piperazin-1-ium (2Z)-3-carb-oxy-prop-2-enoate}, C(23)H(30)N(3)O(+)·C(4)H(3)O(4) (-), the piperazine group in the opipramol cation is protonated at only one of the N atoms. In the cation, the dihedral angle between the two benzene rings is 53.5 (6)°. An extensive array of inter-molecular O-H⋯O, O-H⋯N and N-H⋯O hydrogen bonds and weak inter-molecular N-H⋯O, C-H⋯O and C-H⋯π inter-actions dominate the crystal packing.

[3-(5-Hy-droxy-5H-dibenzo[a,d]cyclo-hepten-5-yl)prop-yl]dimethyl-ammonium 3-carboxyprop-2-enoate.

In the cation of the title salt, C(20)H(24)NO(+)·C(4)H(3)O(4) (-), the N atom in the dimethyl-ammonium group is protonated. The dihedral angle between the mean planes of the two six-membered rings fused to the cyclo-hepten-5-yl ring is 54.4 (1)°. An intra-molecular O-H⋯O hydrogen bond occurs in the anion. The crystal packing is stabilized by inter-molecular O-H⋯O and N-H⋯(O,O) hydrogen bonds and weak C-H⋯O inter-actions, forming a two-dimensional network.

Enrofloxacinium picrate.

There is one cation-anion pair in the asymmetric unit of the title compound [systematic name: 4-(3-carb-oxy-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)-1-ethyl-piperazin-1-ium 2,4,6-tri-nitro-phenolate], C(19)H(23)FN(3)O(3) (+)·C(6)H(2)N(3)O(7) (-). The six-membered piperazine group in the cation adopts a slightly distorted chair conformation and contains a protonated N atom. The dihedral angles between the mean planes of the cyclo-propyl and piperazine rings in the cation with the 10-atom ring system of the quinolone group are 48.1 (1) and 69.9 (5)°, respectively. The picrate anion inter-acts with the protonated N atom of an adjacent cation through a bifurcated N-H⋯O three-center hydrogen bond, forming an R(1) (2)(6) ring motif. Furthermore, there is an intra-molecular O-H⋯O hydrogen bond. The dihedral angle between the mean planes of the anion benzene and cation piperizine, quinoline and cyclo-propyl rings are 61.3 (6), 31.1 (4) and 70.4 (9)°, respectively. The mean planes of the two o-NO(2) and single p-NO(2) groups in the picrate anion are twisted by 6.7 (6), 38.3 (9) and 12.8 (7)° with respect to the mean plane of the benzene ring. Strong N-H⋯O and weak inter-molecular C-H⋯O hydrogen bonds in concert with weak π-π stacking inter-actions [centroid-centroid distances = 3.5785 (13), 3.7451 (12) and 3.6587 (13) Å] dominate the crystal packing.

Lomefloxacinium picrate.

IN THE CATION OF THE TITLE COMPOUND [SYSTEMATIC NAME: (RS)-4-(3-carb-oxy-1-ethyl-6,8-difluoro-4-oxo-1,4-dihydro-quinolin-7-yl)-2-methyl-piperazin-1-ium 2,4,6-trinitro-phenolate], C(17)H(20)F(2)N(3)O(3) (+)·C(6)H(2)N(3)O(7) (-), the piper-azine ring adopts a slightly distorted chair conformation and contains a protonated N atom. An intra-molecular O-H⋯O hydrogen bond occurs in the cation. The dihedral angles between the mean planes of the six-atom piperazine ring and the 10-atom fused ring system is 43.3 (5)°. The picrate anion inter-acts with the protonated N atom of an adjacent cation through a bifurcated N-H⋯(O,O) three-center hydrogen bond. Strong N-H⋯O hydrogen bonds in concert with weak π-π stacking inter-actions [centroid-centroid distance = 3.6460 (14) Å] dominate the crystal packing, creating a two-dimensional network structure along [011].

Cinnarizinium dipicrate.

In the cinnarizinium dication of the title compound {systematic name: 1-diphenyl-methyl-4-[(2E)-3-phenyl-prop-2-en-1-yl]piperazine-1,4-diium bis-(2,4,6-trinitro-phenolate)}, C(26)H(30)N(2) (2+)·2C(6)H(2)N(3)O(7) (-), the piperazine group is protonated at both N atoms and adopts a slightly distorted chair conformation. Strong N-H⋯O(hy-droxy) cation-anion hydrogen bonds link the dication and two anions. In the cation, the (2E)-3-phenyl-prop-2-en-1-yl fragment is disordered over two positions in a ratio of 0.586 (4): 0.414 (4). Two nitro groups in one anion and three in the other one demonstrate rotational disorder. The crystal packing is stabilized by weak inter-molecular π-π [centroid-centroid distances = 3.844 (7), 3.677 (9), 3.825 (5), 3.634 (2) and 3.729 (7) Å], C-H⋯π and C-H⋯O inter-actions.