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The crystal structures and Hirshfeld surface analyses of three Schiff bases, namely ( E )- N '-[4-(piperidin-1-yl)benzyl-idene]benzene-sulfono-hydrazide, C 18 H 21 N 3 O 2 S, (I), ( E )-4-methyl- N '-[4-(piperidin-1-yl)benzyl-idene]benzene-sulfono-hydrazide, C 19 H 23 N 3 O 2 S, (II), and ( E )-4-chloro- N '-[4-(piperidin-1-yl)benzyl-idene]benzene-sulfono-hydrazide, C 18 H 20 ClN 3 O 2 S, (III), derived from aryl-sulfono-hydrazides and 4-(piperidin-4-yl)benzaldehyde have been analysed to investigate the effect of substituents on the structural parameters. All three structures crystallize in monoclinic crystal systems, in the space groups P 2 1 / c for (I) and (II), and C 2/ c for (III). Compound (III) contains two independent mol-ecules in the asymmetric unit and sixteen mol-ecules per unit cell, while (I) and (II) both have one and four mol-ecules, respectively, in their asymmetric units and unit cells. In all cases, the central part of the mol-ecule is twisted at the S atom. In the crystals, the mol-ecules are linked via N-H⋯O hydrogen bonds, forming chains. Two-dimensional fingerprint plots of various inter-atomic contacts show that the major contributions are from H⋯H inter-actions.

Two ( E )- N '-( p -substituted benzyl-idene)-4-chloro-benzene-sulfono-hydrazides, namely, ( E )-4-chloro- N '-(4-chloro-benzyl-idene)benzene-sulfono-hydrazide, C 13 H 10 Cl 2 N 2 O 2 S, (I), and ( E )-4-chloro- N '-(4-nitro-benzyl-idene)benzene-sulfono-hydrazide, C 13 H 10 ClN 3 O 4 S, (II), have been synthesized, characterized and their crystal structures studied to explore the effect of the nature of substituents on the structural parameters. Compound (II) crystallized with two independent mol-ecules [(II A ) and II B )] in the asymmetric unit. In both compounds, the configuration around the C=N bond is E . The mol-ecules are twisted at the S atom with C-S-N-N torsion angles of -62.4 (2)° in (I), and -46.8 (2)° and 56.8 (2)° in the mol-ecules A and B of (II). The 4-chloro-phenyl-sulfonyl and 4-substituted benzyl-idene rings form dihedral angles of 81.0 (1)° in (I), 75.9 (1)° in (II A ) and 73.4 (1)° in (II B ). In the crystal of (I), mol-ecules are linked via pairs of N-H⋯O hydrogen bonds, forming inversion dimers with an R 2 2 (8) ring motif. The dimers are linked by C-Cl⋯π inter-actions, forming a three-dimensional structure. In the crystal of (II), mol-ecules are linked by C-H⋯π inter-actions and N-H⋯O hydrogen bonds, forming - A - B - A - B - chains along the c -axis direction. The chains are linked via C-H⋯O and C-H⋯π inter-actions, forming layers parallel to the bc plane. Two-dimensional fingerprint plots show that the most significant contacts contributing to the Hirshfeld surface for (I) are H⋯H contacts (26.6%), followed by Cl⋯H/H⋯Cl (21.3%), O⋯H/H⋯O (15.5%) and Cl⋯C/C⋯Cl (10.7%), while for (II) the O⋯H/H⋯O contacts are dominant, with a contribution of 34.8%, followed by H⋯H (15.2%), C⋯H/H⋯C (14.0%) and Cl⋯H/H⋯Cl (10.0%) contacts.

The crystal structures of ( E )- N '-(2-chloro-benzyl-idene)-4-nitro-benzene-sulfono-hydrazide, C 13 H 10 ClN 3 O 4 S (I), ( E )- N '-(2-methyl-benzyl-idene)-4-nitro-benzene-sulfono-hydrazide, C 14 H 13 N 3 O 4 S (II), and ( E )- N '-(4-methyl-benzyl-idene)-4-nitro-benzene-sulfono-hydrazide monohydrate, C 14 H 13 N 3 O 4 S·H 2 O (III), have been synthesized, characterized and their crystal structures determined to study the effects of the nature and sites of substitutions on the structural parameters and the hydrogen-bonding inter-actions. All three compounds crystallize in the monoclinic crystal system, with space group P 2 1 for (I) and P 2 1 / c for (II) and (III). Compound (III) crystallizes as a monohydrate. All three compounds adopt an E configuration around the C=N bond. The mol-ecules are bent at the S atom with C-S-N-N torsion angles of -59.0 (3), 58.0 (2) and -70.2 (1)° in (I), (II) and (III), respectively. The sulfono-hydrazide parts are also non-linear, as is evident from the S-N-N-C torsional angles of 159.3 (3), -164.2 (1) and 152.3 (1)° in (I), (II) and (III), respectively, while the hydrazide parts are almost planar with the N-N=C-C torsion angles being -179.1 (3)° in (I), 176.7 (2)° in (II) and 175.0 (2)° in (III). The 4-nitro-substituted phenyl-sulfonyl and 2/4-substituted benzyl-idene rings are inclined to each other by 81.1 (1)° in (I), 81.4 (1)° in (II) and 74.4 (1)° in (III). The compounds show differences in hydrogen-bonding inter-actions. In the crystal of (I), mol-ecules are linked via N-H⋯O hydrogen bonds, forming C (4) chains along the a- axis direction that are inter-connected by weak C-H⋯O hydrogen bonds, generating layers parallel to the ac plane. In the crystal of (II), the amino H atom shows bifurcated N-H⋯O(O) hydrogen bonding with both O atoms of the nitro group generating C (9) chains along the b -axis direction. The chains are linked by weak C-H⋯O hydrogen bonds, forming a three-dimensional framework. In the crystal of (III), mol-ecules are linked by O w -H⋯O, N-H⋯O w and C-H⋯O hydrogen bonds, forming layers lying parallel to the bc plane. The fingerprint plots generated for the three compounds show that for (I) and (II) the O⋯H/H⋯O contacts make the largest contributions, while for the para -substituted compound (III), H⋯H contacts are the major contributors to the Hirshfeld surfaces.

( E )- N '-Benzyl-idene-4-chloro-benzene-sulfono-hydrazide, C 13 H 11 ClN 2 O 2 S, (I), and its ortho - and para -methyl-substituted derivatives, C 14 H 13 ClN 2 O 2 S, namely ( E )-4-chloro- N '-(2-methyl-benzyl-idene)benzene-sulfono-hydrazide, (II), and ( E )-4-chloro- N '-(4-methyl-benzyl-idene)benzene-sulfono-hydrazide, (III), have been synthesized, characterized spectroscopically and their crystal structures determined to investigate the effect of the substitution site of the benzyl-idene group on the structural and supra-molecular features in these compounds. Compounds (I) and (II) are isotypic while compound (III) is different. All three mol-ecules are bent at the S atom with C-S-N-N torsion angles of -66.0 (3), -66.0 (3) and -58.4 (2)° for (I), (II) and (III), respectively. The hydrazone portions of the mol-ecules, S-N-N=C, are slightly twisted from planarity, with a torsion angle of 166.5 (3)° in (I), 165.4 (3)° in (II) and 157.9 (2)° in (III). The two aromatic rings present in the compounds are inclined to each other by 78.4 (2), 74.8 (2) and 76.9 (1)° in (I), (II) and (III), respectively. In the crystal structure of the parent compound (I), and of the ortho -methyl derivative (II), an N-H⋯O hydrogen bond links the mol-ecules into chains along [001], which are inter-connected by weak inter-molecular C-H⋯O inter-actions, generating layers lying parallel to the bc plane. In the crystal of the para derivative (III), however, the packing is significantly different. Here mol-ecules are linked by pairs of N-H⋯O hydrogen bonds, forming inversion dimers with an R 2 2 (8) ring motif. The dimers are then linked by C-Cl⋯π inter-actions, forming ribbons propagating along [10]. Hirshfeld surface analyses show that the van der Waals inter-actions constitute the major contribution to the inter-molecular inter-actions in the crystal structures of all three compounds. The fingerprint plots indicate that the H⋯H contacts make the largest contributions to the Hirshfeld surfaces.

The title compound, C17H16ClN3O2·H2O, an acyl-hydrazone derivative, contains a glycine moiety and two substituted benzene rings on either end of the chain. It crystallized as a monohydrate. The mol-ecules adopt an E conformation with respect to the C=N double bond, as indicated by the N-N=C-C torsion angle of 179.38 (14)°. The mol-ecule is twisted in such a way that the almost planar Car-C(=O)-N(H)-C(H2) and C(H2)-C(=O)N(H)-N=C-Car [r.m.s deviations = 0.009 and 0.025 Å, respectively] segments are inclined to on another by 77.36 (8)°, while the benzene rings are normal to one another, making a dihedral angle of 89.69 (9)°. In the crystal, the water mol-ecule links three mol-ecules through two O-H⋯O and one N-H⋯O hydrogen bonds. The mol-ecules are linked via pairs of N-H⋯O hydrogen bonds, forming inversion dimers with an R 2 (2)(14) ring motif. The dimers are linked by O-H⋯O hydrogen bonds, involving two mol-ecules of water, forming chains along [100], enclosing R 2 (2)(14) and R 2 (2)(18) ring motifs. The chains are linked through C-H⋯O inter-actions, forming sheets parallel to (010). Within the sheets, there are C-H⋯π and parallel slipped π-π stacking inter-actions present [inter-centroid distance = 3.6458 (12) Å].

The title acyl-hydrazone derivative, C17H19N3O3S, containing an amino acid moiety and electron-donating substituents attached to both the phenyl rings, crystallized with two independent mol-ecules (A and B) in the asymmetric unit. The mol-ecules are bent at the S atom, with C-SO2-NH-CH2 torsion angles of -67.3 (2) and 67.7 (3)° in mol-ecules A and B, respectively. Further, the dihedral angles between the sulfonyl-glycine segments and the p-toluene-sulfonyl rings are 76.1 (1) and 85.8 (1)° in mol-ecules A and B, respectively. The central hydrazone segments and the toluene rings attached to them are almost co-planar with their mean planes being inclined to one another by 5.2 (2) (mol-ecule A) and 2.9 (2)° (mol-ecule B). The dihedral angles between the benzene rings are 86.83 (12) (mol-ecule A) and 74.00 (14)° (mol-ecule B). In the crystal, the A mol-ecules are linked by a pair of N-H⋯O hydrogen bonds, forming inversion dimers with an R 2 (2)(8) ring motif. The dimers are linked via three N-H⋯O hydrogen bonds involving the B mol-ecules, forming chains along [100] and enclosing R 2 (2)(12) and R 4 (4)(16) ring motifs. The chains are linked via C-H⋯O hydrogen bonds and a C-H⋯π inter-action, forming sheets parallel to (010). There is a further C-H⋯π inter-action and a slipped parallel π-π inter-action [inter-centroid distance = 3.8773 (16) Å] between the sheets, leading to the formation of a three-dimensional framework.

The mol-ecule of the title compound, C16H16ClN3O3S·H2O, is L-shaped being bent at the S atom; the S-N-C-C torsion angle is 132.0 (3)°. The central part of the mol-ecule, C-C-N-N=C, is almost linear, with the C-C-N-N and C-N-N=C torsion angles being -174.1 (2) and 176.0 (2)°, respectively. The dihedral angle between the p-toluene-sulfonyl ring and the S-N-C-C(=O) segment is 67.5 (4)°, while that between the two aromatic rings is 52.17 (11)°. In the crystal, the water H atom is involved in O-H⋯O hydrogen bonds with a sulfonamide O atom and the carbonyl O atom. The water O atom is itself hydrogen bonded to both NH hydrogen atoms. These four hydrogen bonds lead to the formation of corrugated sheets lying parallel to (100). There are also weak C-H⋯O contacts present within the sheets.

In the title compound, [K(C7H6Cl2NO2S)(H2O)] n , the K(+) cation is hepta-coordinated by two water O atoms, a sulfonyl O atom from each of four different N,4-dichloro-2-methyl-benzene-sulfonamidate anions and a Cl atom of one of the anions. Further, K-O-K bridges form extensive polymeric chains along the b axis. In the crystal structure, the anions are linked into layers parallel to (100) by O-H⋯Cl and O-H⋯N hydrogen bonds.

In the title compound, K(+)·C7H6BrClNO2S(-)·H2O, the K(+) cation is hepta-coordinated by two water O atoms, four sulfonyl O atoms of four different N-bromo-4-chloro-2-methyl-benzene-sulfonamidate anions, and one Br atom of one of the anions. The S-N distance of 1.584 (3) Å is consistent with an S=N double bond. In the crystal, the anions are linked into layers by O-H⋯Br and O-H⋯N hydrogen bonds.

In the title compound, C12H9ClN2O4S, the dihedral angle between the benzene rings is 31.4 (2)°. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into C(4) chains running along the a-axis direction.

In the title compound, C12H8Cl2N2O4S, the N-C bond in the C-SO2-NH-C segment has gauche torsions with respect to the S=O bonds. Further, the N-H bond is syn to the ortho-nitro group in the sulfonyl benzene ring and also syn to both the ortho- and meta-Cl atoms in the aniline ring. The mol-ecule is twisted at the S-N bond with a torsion angle of 61.15 (18)°. The dihedral angle between the planes of the benzene rings is 68.00 (6)°. The amide H atom exhibits an intra-molecular bifurcated N-H⋯(O,O) hydrogen bond. In the crystal, pairs of N-H⋯O(S) hydrogen bonds link the mol-ecules into inversion dimers with R2(2)(8) motifs.

In the title compound, C12H8Cl2N2O4S, the C-S-N-C torsion angle is 49.34 (18)° and the dihedral angle between the benzene rings is 71.92 (10)°. The amide H atom exhibits bifurcated hydrogen bonding. The N-H bond is syn to the ortho-nitro group enabling the formation of an S(7) loop. In the crystal, pairs of N-H⋯O(S) hydrogen bonds link the mol-ecules into inversion dimers via R2(2)(8) rings.

In the title compound, C12H9ClN2O4S, the dihedral angle between the benzene rings is 70.60 (11)°. An intra-molecular N-H⋯Cl contact occurs. In the crystal, mol-ecules form inversion dimers via pairs of N-H⋯O hydrogen bonds.

In the crystal structure of the title compound, C14H14N2O4S, the N-H bond is syn to the ortho-nitro group in the sulfonyl benzene ring and anti to the ortho- and syn to the meta-methyl groups in the aniline ring. The mol-ecule is twisted at the S-N bond with a torsion angle of 71.41 (18)°. The dihedral angle between the planes of the benzene rings is 51.07 (8)°. In the crystal, pairs of N-H⋯Osulfonamide hydrogen bonds link the mol-ecules into inversion dimers.

There are two independent mol-ecules in the asymmetric unit of the title compound, C14H14N2O4S, in which the dihedral angles between the benzene rings are 56.22 (15) and 58.16 (14)°. In the crystal, N-H⋯Onitro hydrogen bonds link the mol-ecules into zigzag chains running along the a-axis direction.

There are two independent mol-ecules in the asymmetric unit of the title compound, C12H9ClN2O4S, in which the dihedral angles between the planes of the benzene rings are 46.90 (14) and 44.50 (14)°. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into zigzag chains parallel to the a axis.

In the title compound, K(+)·C(6)H(4)BrN(2)O(4)S(-)·H(2)O, the K(+) ion is hepta-coordinated by two O atoms from two different water mol-ecules, three sulfonyl O atoms from three N-bromo-2-nitro-benzene-sulfonamidate anions and two nitro O atoms from two N-bromo-2-nitro-benzene-sulfonamidate anions. The S-N distance of 1.576 (4) Å is consistent with an S=N double bond. The crystal structure is stabilized by inter-molecular O-H⋯N and O-H⋯Br hydrogen bonds which link the molecules into polymeric layers running parallel to the bc plane.

There are two independent mol-ecules in the asymmetric unit of the title compound, C(14)H(14)N(2)O(4)S. The N-H bonds are syn to the ortho-nitro groups in the sulfonyl benzene rings and anti to the methyl groups in the aniline benzene rings. The mol-ecules are twisted at the S-N bonds with torsion angles of -60.4 (3) and 58.8 (3)° in the two mol-ecules. The dihedral angles between the planes of the sulfonyl and the anilino benzene rings are 53.67 (8) and 56.99 (9)°. The amide H atoms of both mol-ecules are involved in an intra-molecular hydrogen bond, generating an S(7) motif. In the crystal, pairs of N-H⋯O(S) hydrogen bonds link like mol-ecules into inversion dimers.

The asymmetric unit of the title salt, K(+)·C(6)H(3)BrCl(2)NO(2)S(-)·1.5H(2)O, contains one K(+) cation, one N-bromo-2,4-dichlorobenzenesulfonamidate anion, one water molecule in general position and one water molecule located on a twofold rotation axis. The K(+) cation is hepta-coordinated by three water O atoms and four sulfonyl O atoms from three symmetry-related N-bromo-2,4-dichloro-benzene-sulfonamide anions. The S=N distance of 1.575 (3) Å is consistent with that of a double bond. In the crystal, the anions are linked by O-H⋯Br and O-H⋯N hydrogen bonds into layers parallel to the ac plane.

In the title compound, C(12)H(10)N(2)O(4)S, the dihedral angle between the aromatic rings is 36.19 (18)°. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into C(4) chains running along the a axis.

The asymmetric unit of the title compound, C(14)H(14)N(2)O(4)S, consists of two crystallographically independent mol-ecules. The mol-ecules are twisted at the S-N bonds with C-S-N-C torsion angles of 44.2 (3) and -49.3 (3)°. The dihedral angles between the benzene rings in the two mol-ecules are 71.53 (7) and 72.11 (7)°. The amide H atoms exhibit bifurcated intra- and inter-molecular hydrogen bonds; the intra-molecular N-H⋯O(N) hydrogen bonds generate S(7) motifs. In the crystal, the independent mol-ecules are separately connected through the inter-molecular N-H⋯O(S) hydrogen bonds, generating a C(4) motif and a helical chain along the b axis for one mol-ecule and an R(2) (2)(8) motif and an inversion dimer for the other. The crystal studied was a pseudo-merohedral twin with twin law (-100/0-10/001), the refined ratio of the twin domains being 0.7876 (12):0.2124 (12).

In the crystal of the title compound, C(13)H(12)N(2)O(4)S, the conformation of the N-H bond in the -SO(2)-NH- segment is syn to the ortho-nitro group in the sulfonyl benzene ring. The mol-ecule is twisted at the S-N bond with a torsion angle of 76.55 (18)°. The dihedral angle between the planes of the rings is 72.64 (8)°. In the crystal, mol-ecules are linked by pairs of N-H⋯O(S) hydrogen bonds to form inversion dimers.

In the title compound, C(13)H(12)N(2)O(4)S, the dihedral angle between the benzene rings is 53.44 (14)°. The amide H atom exhibits bifurcated hydrogen bonding: an intra-molecular N-H⋯O hydrogen bond generates an S(7) motif while in the crystal, N-H⋯O(S) hydrogen bonds link the mol-ecules into zigzag C(4) chains along the c axis.

In the title compound, C(13)H(12)N(2)O(4)S, the dihedral angle between the planes of the rings is 51.11 (10)°. In the crystal, mol-ecules are linked into inversion dimers through pairs of N-H⋯O(S) hydrogen bonds.

In the title compound, C(13)H(12)N(2)O(4)S, the dihedral angle between the benzene rings is 73.64 (7)°. The amide H atom exhibits bifurcated hydrogen bonding: an intra-molecular N-H⋯O hydrogen bond generates an S(7) motif while in the crystal, N-H⋯O(S) hydrogen bonds link the mol-ecules into zigzag C(4) chains running along the b axis.

In the title compound, C(12)H(10)N(2)O(4)S, the conformation of the N-H bond in the -SO(2)-NH- fragment is syn to the ortho-nitro group in the sulfonyl-benzene ring. The mol-ecule is twisted at the S-N bond, the C-N-S-C torsion angle being -72.83 (15)°. The dihedral angle between the benzene rings is 59.55 (7)°. The amide H atom and the nitro group O atom form an intra-molecular hydrogen bond, generating an S(7) motif. In the crystal, C-H⋯O hydrogen-bond inter-actions link the mol-ecules into S(2) (2)(10) networks.

In the title compound, C(11)H(14)N(2)OS, the thioamide C=S and amide C=O bonds are anti to each other; the N-H bonds are also anti to each other. The mol-ecular conformation is stabilized by an N-H⋯O hydrogen bond. In the crystal, the mol-ecules are linked into inversion dimers by pairs of N-H⋯S hydrogen bonds.

In the title compound, C(11)H(11)NO(5)S, the dihedral angle between the benzene ring and the amide group is 76.88 (6)°. In the crystal, N-H⋯O(S) and O-H⋯O hydrogen bonds connect the mol-ecules into hydrogen-bonded layers perpendicular to the a axis.

In the title compound, C(11)H(14)N(2)OS, the two N-H bonds are anti to each other and one of them is anti to the C=S and the other is syn. Further, the amide C=S and the C=O groups are anti to each other. The dihedral angle between the benzene ring and the side chain is 83.74 (5)°. An intra-molecular N-H⋯O hydrogen bond occurs. In the crystal, mol-ecules are linked into inversion dimers by pairs of N-H⋯S inter-actions.

In the title compound, C(12)H(9)ClN(2)O(4)S, the dihedral angle between the aromatic rings is 73.65 (7)°. The amide H atom shows bifurcated hydrogen bonding, generating an intra-molecular S(7) and an inter-molecular C(4) motif.

In the title compound, C(12)H(9)ClN(2)O(4)S, the dihedral angle between the aromatic rings is 70.27 (8)°. In the crystal, mol-ecules are linked by pairs of N-H⋯O(S) hydrogen bonds, forming inversion dimers.

In the crystal structure of the title compound, C(11)H(14)N(2)OS, the two N-H bonds are anti to each other. There is an intramolecular N-H⋯O hydrogen bond generating an S(6) ring motif.In the crystal, mol-ecules are linked via N-H⋯S hydrogen bonds with an R(2) (2)(8) motif and N-H⋯O hydrogen bonds with an R(2) (2)(12) motif into chains running along [1-10].

In the title compound, C(9)H(8)Cl(2)N(2)OS, the conformation of one of the N-H bonds is anti to the C=S group and the other is anti to the C=O group. Further, the conformations of the amide C=S and the C=O group are anti to each other. The 2,6-dichloro-phenyl ring and the 3-acetyl-thio-urea side chain are inclined to one another at a dihedral angle of 83.44 (5)°. An intra-molecular N-H⋯O hydrogen bond occurs. In the crystal, mol-ecules form inversion dimers through pairs of N-H⋯S hydrogen bonds.

In the title compound, C(12)H(9)ClN(2)O(4)S, the N-H bond in the -SO(2)-NH- segment is syn to both the ortho-nitro group in the sulfonyl-benzene ring and the ortho-Cl atom in the aniline ring. The mol-ecule is twisted at the S-N bond with a torsion angle of 75.0 (2)°. The dihedral angle between the sulfonyl-benzene and aniline rings is 54.97 (11)°. The amide H atom shows bifurcated hydrogen bonding, generating S(7) and C(4) motifs. In the crystal, N-H⋯O(S) hydrogen bonds link the mol-ecules into chains.

In the crystal structure of the title compound, C(10)H(12)N(2)OS, the conformation of the two N-H bonds are anti to each other. The amide C=O and the C=S are are also anti to each other. The N-H bond adjacent to the benzene ring is syn to the m-methyl groups. The dihedral angle between the benzene ring and the side chain [mean plane of atoms C-C(O)N-C-N; maximum deviation 0.029 (2) Å] is 14.30 (7)°. There is an intramolecular N-H⋯O hydrogen bond generating an S(6) ring motif. In the crystal, the molecules are linked via N-H⋯) hydrogen bonds, forming chains propagating along [001]. The S atom is disordered and was refined using a split model [occupancy ratio 0.56 (4):0.44 (4)].

In the crystal structure of the title compound, C(9)H(8)Cl(2)N(2)OS, there are two mol-ecules in the asymmetric unit which are connected by a pair of N-H⋯S hydrogen bonds. An intra-molecular N-H⋯O hydrogen bond stabilizes the mol-ecular conformation of each molecule.

The title compound, C(11)H(12)ClNO(3), crystallizes with two independent mol-ecules in the asymmetric unit in which the dihedral angles between the benzene ring and the amide group are 55.0 (2) and 28.2 (3)°. The two independent mol-ecules are linked by an N-H⋯O hydrogen bond. In the crystal, mol-ecules form inversion dimers via pairs of O-H⋯O hydrogen bonds. These dimers are linked into sheets parallel to (11-3) via N-H⋯O hydrogen bonds.

The asymmetric unit of the title compound, C(10)H(12)N(2)OS, contains two independent mol-ecules. In both mol-ecules, the conformations of the two N-H bonds are anti to each other. Furthermore, the conformations of the amide C=S bonds and the C=O bonds are anti to each other. The dihedral angles between the benzene ring and the side chain are 52.8 (1) and 68.0 (1)° in the two independent mol-ecules. An intra-molecular N-H⋯O hydrogen bond occurs in both independent mol-ecules. In the crystal, mol-ecules are linked into infinite chains along the a axis through a series of N-H⋯O and N-H⋯S hydrogen bonds.

The asymmetric unit of the title compound, C(16)H(14)Cl(2)N(2)O(6)S(2)·2H(2)O, contains one half-mol-ecule of N,N-bis-(4-chloro-phenyl-sulfon-yl)succinamide, with a centre of symmetry at the mid-point of the central C-C bond, and one water mol-ecule. The succinamide mol-ecules are not directly connected via hydrogen bonds, but by hydrogen bonds via the water mol-ecules.

In the crystal structure of the title compound, C(11)H(14)N(2)OS, the conformation of the two N-H bonds is anti. The conformation of the C=S and the C=O bonds is also anti. Furthermore, the N-H bond adjacent to the benzene ring is anti to the ortho- and meta-methyl groups. The dihedral angle between the benzene ring and the side chain [N-C(= S)-N-C(=O)-C; maximum deviation = 0.047 (4) Å] is 81.33 (10)°. The NH hydrogen adjacent to the benzene ring and the amide O atom exhibit bifurcated intra- and inter-molecular hydrogen bonding. In the crystal, mol-ecules form inversion dimers, which are linked into chains via R(2) (2)(12) and R(2) (2)(8) networks.

In the title compound, C(14)H(12)ClNO, the two aromatic rings are almost coplanar, making a dihedral angle of 4.08 (18)°. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into infinite chains running along the a axis.

In the title compound, C(11)H(12)ClNO(3), the dihedral angle between the benzene ring and the amide group is 44.9 (2)°. In the crystal, mol-ecules form inversion dimers via pairs of O-H⋯O hydrogen bonds. These dimers are further linked into sheets parallel to (013) via N-H⋯O hydrogen bonds.

In the crystal structure of the title compound, C(11)H(13)NO(5)S, the amide C=O and the carboxyl C=O groups of the acid segment orient themselves away from each other. The dihedral angle between the benzene ring and the amide group is 69.0 (2)°. In the crystal, N-H⋯O and O-H⋯O hydrogen bonds link the mol-ecules into layers parallel to the bc plane.

In the title compound, C(14)H(12)ClNO(3)S, the C=O bond is syn to the Cl substituent in the adjacent benzene ring. The C-S-N-C torsion angle is -80.6 (6)°. The chloro-benzoyl ring is disordered and was refined using a split model [occupancy ratio 0.537 (3):0.463 (3)]. In the crystal, mol-ecules are linked by pairs of N-H⋯O(S) hydrogen bonds, forming inversion dimers.

In the title compound, C(15)H(14)ClNO, the dihedral angle between the benzoyl and the aniline rings is 3.30 (18)°. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into chains running along the a axis.

The asymmetric unit of the title compound, C(14)H(13)NO(3)S, contains three independent mol-ecules in which the dihedral angles between the sulfonyl and benzoyl benzene rings are 83.3 (2), 84.4 (2) and 87.6 (2)°. In the crystal, mol-ecules are linked into chains running along the a axis via N-H⋯O hydrogen bonds.

In the title compound, C(13)H(10)N(2)O(5)S, the C=O bond in the -SO(2)-NH-CO- segment is anti to the meta-nitro group in the benzoyl ring, while the N-C bond has gauche torsions with respect to the S=O bonds. The molecule is twisted at the N atom with a dihedral angle of 79.9 (2)° between the sulfonyl benzene ring and the -SO(2)-NH-CO- segment. Furthermore, the dihedral angle between the benzeneline rings is 86.9 (2)°. In the structure, the mol-ecules are linked into helical chains along the b axis via N-H⋯O hydrogen bonds.

In the title compound, C(10)H(9)ClN(2)O(5), the nitro group is significantly twisted out of the plane of the benzene ring to which it is attached [dihedral angle = 27.4 (6)°]. In the crystal, mol-ecules are linked into centrosymmetric dimers via pairs of O-H⋯O hydrogen bonds. These dimers are further linked by N-H⋯O hydrogen bonds into double chains running along the a axis.

In the crystal structure of the title compound, C(11)H(12)ClNO(3), the asymmetric unit contains two independent mol-ecules. The N-H bond in the amide segment is anti to the meta-Cl atom in the benzene ring, in both molecules. The amide and carboxyl C=O bonds are also anti to each other and anti to the H atoms on the adjacent -CH(2) groups. Furthermore, the C=O and O-H bonds of the acid group are in syn positions with respect to each other. The dihedral angles between the benzene ring and the amide group are 40.6 (2) and 44.9 (3)° in the two independent molecules. In the crystal, mol-ecules are packed into sheets parallel to the (11-3) plane through O-H⋯O and N-H⋯O hydrogen bonds.

In the structure of the title compound, C(14)H(12)ClNO, the ortho-Cl atom in the benzoyl ring is positioned syn to the C=O bond, while the meta-methyl group in the aniline ring is positioned anti to the N-H bond. The amide group forms dihedral angles of 60.1 (1) and 22.0 (1)°, respectively, with the benzoyl and aniline rings, while the angle between these rings is 38.7 (1)°. The crystal structure is stabilized by N-H⋯O hydrogen bonds, which give rise to infinite chains running along the c axis.