2-Nitro-benzyl methane-sulfonate.

In the title compound, C8H9NO5S, the dihedral angle between the benzene ring and the nitro group is 5.86 (15)° and the C-C-O-S group adopts an anti conformation [torsion angle = -168.44 (15)°]. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, generating a three-dimensional network.

Bis(2-bromo-benz-yl) ether.

In the title compound, C14H12Br2O, the dihedral angle between the aromatic rings is 2.7 (3)° and the Br atoms lie on the same side of the mol-ecule. No inter-molecular inter-actions occur in the crystal beyond van der Waals contacts.

1-(3-Oxo-3-phenyl-prop-yl)piperidinium chloride.

In the title salt, C14H20NO(+)·Cl(-), the piperidine ring adopts a chair conformation. In the crystal, the cations and anions are linked by classical N-H⋯Cl hydrogen bond and weak C-H⋯Cl and C-H⋯O hydrogen bonds; the C-H⋯O hydrogen bonds exhibit R 2 (2)(14) ring motifs while the C-H⋯Cl hydrogen bonds link the mol-ecules into chains along the a-axis direction. π-π stacking is observed between parallel phenyl rings of adjacent cations, the centroid-centroid distance being 3.8164 (15) Å.

Methyl 2-{2-[(2-methyl-phen-oxy)meth-yl]phen-yl}-2-oxoacetate.

In the title compound, C17H16O4, the dihedral angle between the benzene rings is 4.4 (2)°. In the crystal, weak C-H⋯O hydrogen bonds connect mol-ecules along [001].

Amicarbazone.

Three independent mol-ecules comprise the asymmetric unit of the title compound, C10H19N5O2, (systematic name: 4-amino-N-tert-butyl-3-isopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazole-1-carboxamide) . In all three mol-ecules, the triazole ring and the carboxamide group are almost coplanar [within 4.0-5.9 (9)°], particularly because of the formation of an intra-molecular N-H⋯O hydrogen bond. On other hand, the orientation of the isopropyl group varies significantly from mol-ecule to mol-ecule. The crystal packing is dominated by N-H⋯O and N-H⋯N hydrogen bonds, which connect the mol-ecules into infinite chains along [010].

Orphenadrinium dihydrogen citrate.

In the title salt, C(18)H(24)NO(+)·C(6)H(7)O(7) (-), the dihedral angle between the benzene rings in the cation is 74.2 (5)°. In the crystal, anion-anion O-H⋯O hydrogen bonds and weak O-H⋯O inter-actions form infinite chains along [100]. Between these chains, cation-anion N-H-O hydrogen bonds are observed, forming an alternate pattern of cation and anion layers and leading to a two-dimensional network parallel to (100).

Tramadolium picrate.

In the title salt {systematic name: [2-hy-droxy-3-(3-meth-oxy-phen-yl)cyclo-hexyl-meth-yl]dimethyl-aza-nium 2,4,6-trinitro-phenol-ate}, C(16)H(26)NO(2) (+)·C(6)H(2)N(3)O(7) (-), the cation is protonated at the N atom. The cyclo-hexane ring adopts a chair conformation with the hy-droxy substituent in an axial position. In the crystal, O-H⋯O and N-H⋯O hydrogen bonds link the cations and anions into supra-molecular chains along [100].

1,3-Bis(biphenyl-4-yl)-2,2-dibromo-3-oxopropyl acetate.

In the title compound, C(29)H(22)Br(2)O(3), the dihedral angles between the mean planes of the benzene rings within each biphenyl group are 26.7 (8) and 30.9 (8)°. The mean planes of the terminal and inner benzene rings of the biphenyl groups bonded through a propan-1-one group in the V-shaped mol-ecule are oriented at angles of 66.1 (7) and 60.0 (8)°, respectively. The two Br atoms are opposite the propen-1-one group. Weak inter-molecular C-H⋯O and C-H⋯π inter-actions are observed in the crystal structure.

(2E)-3-[4-(Dimethyl-amino)-phen-yl]-1-(4-fluoro-phen-yl)prop-2-en-1-one.

The mean planes of the two benzene rings in the title compound, C(17)H(16)FNO, 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 inter-molecular C-H⋯O inter-actions link pairs of mol-ecules, forming centrosymmetric dimers.

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.

(2E)-3-(3-Bromo-4-meth-oxy-phen-yl)-1-(4-fluoro-phen-yl)prop-2-en-1-one.

In the title compound, C(16)H(12)BrFO(2), the dihedral angle between the aromatic rings is 23.75 (12)° and the dihedral angle between the prop-2-en-1-one fragment and the fluorobenzene ring is 20.9 (2)°. In the crystal, only van der Waals interactions occur.

4-(4-Chloro-phen-yl)-4-hy-droxy-piperidinium benzoate.

In the title salt, C(11)H(15)ClNO(+)·C(7)H(5)O(2) (-), the dihedral angle between the mean planes of the chloro-phenyl ring of the cation and the benzene ring of the anion is 74.4 (1)°. In the cation, the six-membered piperazine ring adopts a chair conformation. The crystal packing is stabilized by inter-molecular N-H⋯O and O-H⋯O hydrogen bonds, and weak inter-molecular C-H⋯O, C-H⋯Cl and C-H⋯π inter-actions.

4-(4-Chloro-phen-yl)-4-hy-droxy-piperidinium 2-(2-phenyl-eth-yl)benzoate.

In the title compound, C(11)H(15)ClNO(+)·C(15)H(13)O(2) (-), the piperidinium ring adopts a chair conformation. In the crystal, cations and anions are connected by inter-molecular O-H⋯O and N-H⋯O hydrogen bonds, forming two-dimensional networks parallel to the bc plane. Furthermore, the crystal structure is stabilized by weak C-H⋯π inter-actions.

(2E)-3-(3-Bromo-4-meth-oxy-phen-yl)-1-(4-methyl-phen-yl)prop-2-en-1-one.

The overall shape of the mol-ecule of the title compound, C(17)H(15)BrO(2), can be described by the dihedral angles between three planar fragments: 1-bromo-2-meth-oxy-phenyl ring [maximum deviation = 0.003 (2) Å], the central prop-2-en-1-one chain [maximum deviation = 0.005 (2) Å], and the methyl-phenyl ring [maximum deviation = 0.004 (2) Å]. The terminal planes are twisted by 10.37 (12)°, while the central plane is almost coplanar with the methyl-phenyl ring [3.30 (13)°], but the dihedral angle with the other phenyl ring is significantly larger [8.76 (16)°]. In the crystal, mol-ecules are linked into chains along [001] by three C-H⋯O hydrogen bonds. These chains inter-act with each other by means of weak π-π contacts [centroid-centroid distances = 3.73 (1) and 3.44 (1) Å]. An inter-molecular C-H⋯Br inter-action also occurs.

2-(2-Benzyl-phen-yl)propan-2-ol.

There are two mol-ecules in the asymmetric unit of the title compound, C(16)H(18)O, a tertiary alcohol featuring a 2-benzyl-phenyl substituent. Co-operative O-H⋯O hydrogen bonds connect the mol-ecules into tetra-mers.

Tramadol hydro-chloride-benzoic acid (1/1).

In the cation of the title co-crystal salt {systematic name: [2-hydroxy-2-(3-meth-oxy-phen-yl)cyclo-hexyl-meth-yl]dimethyl-aza-nium chloride-benzoic acid (1/1)}, C(16)H(31)NO(2) (+)·Cl(-)·C(7)H(6)O(2), the N atom is protonated and the six-membered cyclo-hexane ring adopts a slightly distorted chair conformation. The dihedral angle between the mean planes of the benzene rings in the cation and the benzoic acid mol-ecule is 75.5 (9)°. The crystal packing is stabilized by weak inter-molecular O-H⋯Cl, N-H⋯Cl and C-H⋯π inter-actions, forming a two-dimensional chain network along the b axis. The benzoic acid mol-ecule is not involved in the usual head-to-tail dimer bonding, but instead is linked to the ammonium cation through mutual hydrogen-bonding inter-actions with the chloride anion.

9,9-Dimethyl-9,10-dihydroanthracene.

In the title compound, C(16)H(16), the central benzene ring adopts a boat conformation, with a dihedral angle of 34.7 (9)° between the mean planes of the two fused benzene rings. The two methyl groups at the apex of the central benzene ring are in axial and equatorial conformations. The crystal packing is stabilized by weak C-H⋯π inter-molecular inter-actions.

2-Chloro-N-[2-(2-fluoro-benzo-yl)-4-nitro-phen-yl]-N-methyl-acetamide.

The title compound, C(16)H(12)ClFN(2)O(4), crystallizes with two mol-ecules in the asymmetric unit in which the dihedral angles between the mean planes of the two benzene rings are 65.1 (7) and 65.6 (6)°. In each mol-ecule, the nitro group displays rotational disorder over two orientations in a 0.503 (11):0.497 (11) ratio and the Cl atom is disordered in a 0.432 (5):0.568 (5) ratio. In one mol-ecule, the F atoms is statistically disordered over two positions. The crystal packing features weak inter-molecular C-H⋯O and C-H⋯Cl inter-actions, which form a layered network.

Orphenadrinium picrate.

In the title molecular salt {systematic name: N,N-dimethyl-2-[(2-methyl-phen-yl)(phen-yl)meth-oxy]ethanaminium 2,4,6-tri-nitro-phenolate}, C(18)H(24)NO(+)·C(6)H(2)N(3)O(7) (-), the phenyl rings of the orphenadrinum cation are disordered [occupancies = 0.662 (4) and 0.338 (4)]. The N atom in the orphenadrinum cation is protonated. The picrate anion inter-acts with the protonated N atom through a bifurcated N-H⋯O hydrogen bond, forming an R(1) (2)(6) ring motif with an adjacent cation. The mean planes of the two o-NO(2) and single p-NO(2) groups in the picrate anion are twisted by 23.0 (6), 31.3 (3) and 6.3 (2)° with respect to the mean planes of the six-membered ring. Weak inter-molecular C-H⋯O hydrogen bonds, C-H⋯π inter-molecular inter-actions and weak π-π stacking inter-actions [centroid-centroid distances = 3.677 (2) and 3.515 (3) Å} stabilize the crystal packing, creating a three-dimensional network.

Bis[4-(4-chloro-phen-yl)-4-hydroxy-piperidinium] dipicrate dimethyl sulfoxide solvate.

The asymmetric unit of the title salt solvate, 2C(11)H(15)ClNO(+)·2C(6)H(2)N(3)O(7) (-)·C(2)H(6)OS, contains two crystallographically independent 4-(4-chloro-phen-yl)-4-hydroxy-piperidinium cations, two picrate anions and a dimethyl sulfoxide solvent mol-ecule. In each cation, the piperidinium ring adopts a chair conformation. In the crystal structure, the cations, anions and solvent mol-ecules are connected by inter-molecular O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds, forming a three-dimensional network.