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In the mol­ecular structure of the title compound, C20H26ClNO3S, the six-membered ring of the bornane unit shows a boat conformation, while the five-membered ring of the sultam unit adopts a twist conformation. In the crystal structure, mol­ecules are connected by inter­molecular C—H⋯O hydrogen bonds into a chain running along the b axis. Intramolecular C—H⋯O and C—H⋯N hydrogen bonds are also present.

In the mol­ecular structure of the title compound, C19H24ClNO3S, the six-membered ring of the bornane unit shows a boat form, while the five-membered ring of the sultam unit adopts a twist form. Intra­molecular C—H⋯N and C—H⋯O inter­actions are observed. In the crystal structure, mol­ecules are connected by inter­molecular C—H⋯O hydrogen bonds into a chain running along the b axis. The crystal was a partial inversion twin with a twin ratio of 0.73 (1):0.27 (1).

The title compound, C26H25Cl3N6O4, was prepared by the reaction of (Z)-ethyl 3-amino-3-(4-chloro­phen­yl)-2-cyano­acrylate and 4-chloro-3-ethyl-1-methyl-1H-pyrazole-5-carbonyl chloride. The dihedral angles between the chloro­benzene and the two pyrazole rings are 59.8 (2) and 33.3 (2)°. The two pyrazole rings are oriented to each other at a dihedral angle of 84.7 (2)°. The crystal packing is governed by inter­molecular C—H⋯O inter­actions, resulting in a three-dimensional network. The ethyl groups are disordered over two positions, with site-occupancy factors of 0.71/0.29 and 0.51/0.49.

In the title compound, C21H20N2O4, the naphthalene ring system makes a dihedral angle of 84.5 (3)° with the benzene ring, and the –C(=O)–N(H)–N(H)–C(=O)– torsion angle is 70.7 (7)°, so that the mol­ecule is twisted. An S(6) ring motif is formed via an intra­molecular O—H⋯O hydrogen bond. In the crystal, mol­ecules are linked by N—H⋯O and C–H⋯O hydrogen bonds into supra­molecular layers in the ab plane.

In the title hydroxamic acid derivative, C22H16Cl2N2O5, the nitro-substituted benzene ring forms dihedral angles of 26.95 (15) and 87.06 (15)°, with the 4-chloro- and 2-chloro-substituted benzene rings, respectively. The dihedral angle between the chloro-substituted benzene rings is 68.19 (13)°. The O atoms of the nitro group were refined as disordered over two sets of sites with equal occupancies. In the crystal, weak C—H⋯O(=C) hydrogen bonds link mol­ecules along [100].

The title compound, C10H11N3O4·C2H4O2, was prepared by an electrochemical technique. In the crystal, acetic acid mol­ecules are involved in hydrogen bonding to two separate propano­ylurea mol­ecules, acting as a donor in an O—H⋯O inter­action and as an acceptor in two N—H⋯O inter­actions. The propano­ylurea mol­ecules inter­act with each other via N—H⋯O hydrogen bonds. C—H⋯O inter­actions also stabilize the crystal structure.

The asymmetric unit of the title compound, C27H30N2O2, comprises two independent mol­ecules. The dihedral angles between the phenyl rings in the two mol­ecules are 55.59 (8) and 55.39 (8)°. The piperidine rings adopt chair conformations. The crystal structure is stabilized by weak inter­molecular C—H⋯O and C—H⋯N hydrogen bonds. The crystal studied was a non-merohedral twin with a domian ratio of 0.75 (2):0.25 (2).

In the title compound, C17H11Br3N2O3, the whole mol­ecule is disordered over two positions with a refined occupancy ratio of 0.770 (5):0.230 (5). In the major component, the 1,2,3-oxadiazo­lidine ring is essentially planar [maximum deviation = 0.017 (6) Å] and makes dihedral angles of 22.5 (3) and 70.2 (3)° with the 4-bromo­phenyl and phenyl rings, respectively. In the minor component, the corresponding values are 18.9 (11) and 84.9 (12)°. In the crystal, inter­molecular C—H⋯Br hydrogen bonds link the mol­ecules into ribbons along [010]. There is a short O⋯N contact [2.83 (3) Å] in the minor component. In the major component, the mol­ecular structure is stabilized by an intra­molecular C—H⋯O hydrogen bond, which forms an S(6) ring motif.

In the anion of the title mol­ecular salt, C4H12N2 2+·C11H10O6 2−, the two acetate groups form torsion angles of 74.1 (1) and 7.1 (1)° with the central benzene ring, and the cation exhibits a chair conformation. In the crystal, N—H⋯O hydrogen bonds link the components into a two-dimensional supra­molecular network lying parallel to the ab plane. A number of C—H⋯O inter­actions consolidate the packing.

In the title mol­ecule, C22H17ClN2O5, the nitro-substituted benzene ring makes a dihedral angle of 79.22 (1)° with the benzoyl ring and 53.03 (1)° with the chloro-substituted benzene ring. An intra­molecular C—H⋯O hydrogen bond occurs. The crystal structure features weak C—H⋯Cl and C—H⋯O inter­actions.

In the title compound, C29H34N2O2, the central piperidine ring adopts a half-chair conformation, whereas the terminal one adopts a chair conformation. The mean plane of the central piperidine ring [maximum deviation = 0.384 (2) Å] makes dihedral angles of 64.82 (13) and 17.55 (13)° with the benzene rings. In the crystal, mol­ecules are linked into a tape along the b axis via C—H⋯O inter­actions, generating R 2 2(20) and R 2 1(6) graph-set motifs. C—H⋯π inter­actions are observed between the tapes.

In the title compound, C15H19N3O6, the amide planes are inclined at dihedral angles of 0.8 (6) and 12.1 (3)° with respect to the central pyridine ring. The mean planes of the corresponding methyl acetate groups form dihedral angles of 41.76 (13) and 86.48 (15)°, respectively with the mean plane of pyridine ring. A pair of weak intra­molecular N—H⋯N hydrogen bonds generate an S(5)S(5) ring motif in the mol­ecule. In the crystal, mol­ecules are linked by N—H⋯O hydrogen bonds into [001] chains. The chains are cross-linked by C—H⋯O hydrogen bonds into layers lying parallel to bc plane. The crystal packing also features a C—H⋯π inter­action.

In the title compound, C12H14N2O3S, the propyl acetate group and the benzoyl group adopt a cis–trans conformation, respectively, with respect to the thiono S atom across the C—N bonds. The phenyl ring is twisted relative to the the thio­urea mean plane, forming a dihedral angle of 24.16 (9)°. An intra­molecular N—H⋯O hydrogen bond occurs. The crystal packing is stabilized by inter­molecular N—H⋯O and C—H⋯O hydrogen bonds, forming a chain along the a axis.

In the title compound, C21H25N3O6S, the dihedral angle between the meth­oxy­benzene and indazole rings is 74.96 (5)°. The crystal packing is stabilized by an N—H⋯O hydrogen bond into a two-dimensional network. In addition, C—H⋯π inter­actions and a π–π contact, with a centroid–centroid distance of 3.5333 (6) Å, are observed. The crystal packing is stabilized by N—H⋯O and C—H⋯O hydrogen bonds.

In the title mol­ecular salt, C18H15ClNO+·ClO4 −, the quinolin­ium ring system is approximately planar, with a maximum deviation of 0.027 (1) Å. The dihedral angle formed between the mean planes of the quinolinium ring system and the benzene ring is 78.46 (3)°. In the crystal structure, inter­molecular N—H⋯O and C—H⋯O hydrogen bonds link the cations and anions into a three-dimensional network. The crystal structure is further consolidated by C—H⋯π inter­actions.

The title compound, C6H11N3O3·0.5H2O, has two independent mol­ecules and one mol­ecule of water in the asymmetric unit. The crystal packing is stabilized by inter­molecular N—H⋯N, O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds. These inter­actions form a two-dimensional array in the ab plane with a zigzag motif which has an angle close to 35° between the zigzag planes. The hydrogen bonding can be best described using the graph-set notation as N 1 = C(10)R 2 2(10)R 2 2(8) and N 2 = R 6 4(20)R 2 2(8).

The asymmetric unit of the title compound, C21H25ClN2O, contains four crystallographically independent mol­ecules, which differ mainly in the orientation of the isobutyl groups. The benzene rings are almost orthogonal to each other, forming dihedral angles of 87.40 (6), 88.69 (6), 84.88 (6) and 85.12 (6)° in the four mol­ecules. The crystal structure is stabilized by inter­molecular N—H⋯O and C—H⋯O hydrogen bonds, together with C—H⋯π inter­actions.

In the title compound, C21H26ClN2O4S.Cl, also known as tianeptine hydro­chloride, the seven-membered ring adopts a boat conformation. The dihedral angle between the mean planes of the benzene rings is 44.44 (7)°. There is an intra­molecular hydrogen bond formed via S= O⋯H—N. In the crystal, mol­ecules are connected via pairs of N—H.·O, N—H⋯Cl and O—H⋯Cl hydrogen bonds, forming inversion dimers, which are consolidated by C—H⋯O inter­actions. The dimers are linked by C—H⋯O and C—H⋯Cl inter­actions, forming a two-dimensional network lying parallel to (011).

In the zwitterionic title compound, C18H16N2O4·H2O, the dihedral angle between the planes of the benzene and indole rings is 39.20 (8)°. An intra­molecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, inter­molecular hy­droxy and water O—H⋯O(carboxyl­ate) and N+—H⋯O(carboxyl­ate) and indole N—H⋯O(water) hydrogen bonds give a three-dimensional structure.

In the title compound, C15H10Cl3NO2, an intra­molecular N—H⋯O hydrogen bond forms a six-membered ring and enforces an almost coplanar conformation for the acetamido group, the central benzene ring and the bridging carbonyl C—C(=O)—C group: the dihedral angles between the benzene ring and the acetamide and carbonyl C—C(=O)—C planes are 7.06 (11) and 7.17 (12)°, respectively. The dihedral angle between the two benzene rings is 67.43 (9)°. Because a strong hydrogen-bond donor is involved in the intra­molecular inter­action, the crystal packing is determined by weak C—H⋯O and C—H⋯Cl inter­actions.

In the title mol­ecule, C24H18ClNO6S, the heterocyclic thia­zine ring adopts a half-chair conformation with the S and N atoms displaced by 0.406 (5) and 0.444 (5) Å, respectively, on opposite sides of the mean plane formed by the remaining ring atoms. The meth­oxy­benzoyl and the chloro­phenyl rings lie roughly parallel to each other, with a dihedral angle between the mean planes of these rings of 8.86 (10)°. The mol­ecular structure is consolidated by intra­molecular O—H⋯O and C—H⋯O inter­actions and the crystal packing is stabilized by inter­molecular O—H⋯O and C—H⋯Cl hydrogen bonds.

The title benzamide derivative, C14H12ClNO2, crystallizes with two independent mol­ecules in the asymmetric unit. Both are close to being planar, with dihedral angles between the two benzene rings of 11.92 (6) and 12.80 (7)°. In the crystal structure, N—H⋯O hydrogen bonds link mol­ecules into chains along a. These inter­actions are augmented by C—H⋯O hydrogen bonds to form two-dimensional layers in the ac plane. Additional C—H⋯O inter­actions result in a three-dimensional network consisting of undulating rows along c. The crystal studied was an inversion twin with a 0.59 (3):0.41 (3) domain ratio.

In the title compound, C27H20ClNO, the quinoline ring forms a dihedral angle of 62.53 (5)° with the substituent benzene ring. In the crystal, inter­molecular C—H⋯Cl inter­actions link the mol­ecules into chains along the b axis. Inter­molecular C—H⋯N and C—H⋯O hydrogen bonds further consolidate the structure into a three-dimensional network. The unit cell contains four solvent-accessible voids, each with a volume of 35 Å3, but no significant electron density was found in them.

In the title compound, C12H16N2OS, an intra­molecular N—H⋯O hydrogen bond forms an S(6) ring motif. The propionyl­thio­urea group is approximately planar [with a maximum deviation of 0.135 (2) Å] and forms a dihedral angle of 83.39 (7)° with the benzene ring. In the crystal, mol­ecules are linked by pairs of N—H⋯S hydrogen bonds, forming centrosymmetric dimers and generating R 2 2(8) ring motifs.

In the title benzamide derivative, C11H14ClNO, the chloro­benzene and butyl­amine groups are each planar, with mean deviations from the planes of 0.013 and 0.030 Å, respectively, and a dihedral angle of 2.54 (9)° between the two planes. In the crystal structure, N—H⋯O hydrogen bonds link mol­ecules in rows along a. Short inter­molecular Cl⋯Cl inter­actions [3.4225 (5) Å] link these rows into sheets in the ac plane. Additional weak C—H⋯O and C—H⋯π inter­actions generate a three-dimensional network.