N-(4-Chloro-phen-yl)-N'-(3-methyl-phen-yl)succinamide monohydrate.

In the title hydrate, C(17)H(17)ClN(2)O(2)·H(2)O, the dihedral angles formed by the aromatic rings of the chloro-benzene and methyl-benzene groups with the mean planes of their attached NH-C(O)-CH(2) fragments are 16.6 (2) and 22.8 (2)°, respectively. In the crystal, O-H⋯O and N-H⋯O hydrogen bonds link the components into a two-dimensional network parallel to the ab plane.

N-(4-Chloro-phenyl)-N'-(4-methyl-phen-yl)succinamide.

The asymmetric unit of the title compound, C(17)H(17)ClN(2)O(2), contains one half-mol-ecule with a center of symmetry at the mid-point of the central C-C bond. The dihedral angle between the benzene ring and the adjacent NH-C(O)-CH(2) group is 39.9 (1)°. The methyl and Cl groups are disordered with respect to the para-positions of the benzene ring, with site-occupation factors of 0.5 each. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into chains parallel to the baxis.

N-(2,6-Dichloro-phen-yl)succinamic acid.

In the crystal of the title compound, C(10)H(9)Cl(2)NO(3), the conformations of the amide O atom and the carbonyl O atom of the acid segment are anti to each other and to the H atoms on the adjacent -CH(2) groups. The C=O and O-H bonds of the acid group are syn to one another. In the crystal, mol-ecules are packed into infinite chains through inter-molecular O-H⋯O and N-H⋯O hydrogen bonds.

N-(2,5-Dimethyl-phen-yl)succinamic acid monohydrate.

In the title compound, C(12)H(15)NO(3)·H(2)O, the conformation of the N-H bond in the amide segment is syn to the ortho-methyl group and anti to the meta-methyl group in the benzene ring. Further, the conformations of the amide O and the carbonyl O atom of the acid segment are anti to the adjacent methyl-ene H atoms. The C=O and O-H bonds of the acid group are syn to one another. The structure shows an inter-esting hydrogen-bonding pattern with the water mol-ecule forming hydrogen bonds with three different mol-ecules of the compound. In the crystal, mol-ecules are packed into infinite chains through inter-molecular O-H⋯O and N-H⋯O hydrogen bonds.

N-(3-Chloro-phen-yl)succinimide.

In the title compound, C(10)H(8)ClNO(2), the chloro-benzene and the essentially planar (r.m.s. deviation = 0.030 Å) pyrrolidine ring are tilted by 59.5 (1)° with respect to one another.

N-(3-Chloro-phen-yl)-N'-(3-methyl-phen-yl)succinamide.

The asymmetric unit of the title compound, C(17)H(17)ClN(2)O(2), contains one half-mol-ecule with a center of inversion at the mid-point of the central C-C bond. The amide N-H group is anti to the meta-chloro/methyl groups in the adjacent benzene rings. The dihedral angle between the benzene ring and the NH-C(O)-CH(2) segment is 43.5 (1)°. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into chains along the a axis. The methyl group and the Cl atom occupy the same position and were treated in a disorder model with site-occupation factors of 0.5 each.

N-(2,5-Dichloro-phen-yl)succinamic acid.

In the title compound, C(10)H(9)Cl(2)NO(3), the conformation of the N-H bond in the amide segment is syn with respect to the ortho-Cl atom and anti to the meta-Cl atom of the benzene ring. In the crystal, inter-molecular O-H⋯O and N-H⋯O hydrogen bonds pack the mol-ecules into two types of chains along the a and b axes, respectively, leading to an overall sheet structure. The acid group in the side chain is disordered and was refined using a split model with site-occupation factors of 0.60:0.40.

N-(2-Chloro-phen-yl)-N'-(2-methyl-phen-yl)succinamide.

In the title compound, C(17)H(17)ClN(2)O(2), the asymmetric unit contains half a mol-ecule with a centre of symmetry at the mid-point of the central C-C bond. The conformations of the amide O atoms are anti to the methyl-ene atoms. Further, the N-H bonds in the amide fragments are anti to the ortho-chloro/methyl groups in the adjacent benzene rings. The dihedral angle between the benzene ring and the NH-C(O)-CH(2) segment in the two halves of the mol-ecule is 62.0 (2)°. In the crystal, a series of N-H⋯O inter-molecular hydrogen bonds link the mol-ecules into column-like infinite chains along the a axis. The methyl and Cl groups are disordered with respect to the ortho positions of the benzene ring, with site-occupation factors of 0.5 each.

N,N'-Bis(3-methyl-phen-yl)succinamide dihydrate.

The asymmetric unit of the title compound, C(18)H(20)N(2)O(2)·2H(2)O, contains half a mol-ecule with a center of symmetry at the mid-point of the central C-C bond. The N-H bonds in the amide fragments are anti to the meta-methyl groups in the adjacent benzene rings. The dihedral angle between the benzene ring and the NH-C(O)-CH(2) segment in the two halves of the mol-ecule is 5.6 (4)°. In the crystal, the packing of mol-ecules through O-H⋯O and N-H⋯O hydrogen-bonding inter-actions leads to the formation of layers parallel to the bc plane. The methyl group is disordered with respect to the 3- and 5-positions of the benzene ring, with site-occupation factors of 0.910 (8) and 0.090 (8).

N-(4-Methyl-phen-yl)-N'-phenyl-butane-diamide monohydrate.

In the title hydrate, C(17)H(18)N(2)O(2)·H(2)O, the dihedral angles formed by the aromatic rings of the benzene and methyl-benzene groups with the mean planes of the attached NH-C(O)-CH(2) fragments are 12.6 (4) and 23.3 (3)°, respectively, while that between the two aromatic rings is 73.7 (2)°. In the crystal, the water mol-ecule accepts two and makes two hydrogen bonds. The mol-ecules are packed into layers parallel to (101) by O-H⋯O and N-H⋯O hydrogen-bonding inter-actions.

N,N'-Bis(3-chloro-phen-yl)succinamide.

The complete molecule of the title compound, C(16)H(14)Cl(2)N(2)O(2), is generated by crystallographic inversion symmetry. The dihedral angle between the benzene ring and the NH-C(O)-C fragment is 32.8 (1)°. In the crystal, the molecules are linked by N-H⋯O hydrogen bonds into [100] chains.

N,N'-Bis(2-chloro-phen-yl)succinamide.

There is one half-mol-ecule in the asymmetric unit of the title compound, C(16)H(14)Cl(2)N(2)O(2), with a center of symmetry at the mid-point of the central C-C bond. The N-H and C=O bonds in the C-NH-C(O)-C fragment are anti to each other and the amide O atom is anti to the H atoms attached to the adjacent C atoms. However, the conformation of the N-H bond in the amide fragments is syn to the ortho-chloro groups in the adjacent benzene rings. The dihedral angle between the benzene ring and the NH-C(O)-CH(2) fragment is 47.0 (2)°. In the crystal, a series of N-H⋯O inter-molecular hydrogen bonds link the mol-ecules into chains along the b axis.

N-(3-Chloro-phen-yl)-N'-(2-methyl-phenyl)succinamide monohydrate.

In the title compound, C(17)H(17)ClN(2)O(2)·H(2)O, the dihedral angles formed by the aromatic rings of the chloro-benzene and methyl-benzene groups with the mean planes of the attached NH-C(O)-CH(2) fragments are 9.4 (4) and 62.9 (2)°, respectively. In the crystal, mol-ecules are packed into layers parallel to the bc plane by O-H⋯O and N-H⋯O hydrogen-bond inter-actions.

N,N'-Bis(2-methyl-phen-yl)succinamide.

In the title compound, C(18)H(20)N(2)O(2), the conformations of the N-H and C=O bonds in the C-NH-C(O)-C segments are anti to each other and the amide O atom is anti to the H atoms attached to the adjacent C atoms. Further, the conformations of the N-H bonds in the amide fragments are anti to the ortho-methyl groups in the adjacent benzene rings. The complete molecule is generated by inversion symmetry. The dihedral angle between the benzene ring and the NH-C(O)-CH(2) segment in the two halves of the mol-ecule is 62.1 (2)°. In the crystal, N-H⋯O inter-molecular hydrogen bonds link the mol-ecules into sheet-like infinite chains along the a axis.

N-Phenyl-succinamic acid.

In the crystal structure of the title compound, C(10)H(11)NO(3), the conformations of N-H and C=O bonds in the amide segment are anti to each other. Further, the conformations of the amide O atom and the carbonyl O atom of the acid segment are anti to each other and to the adjacent -CH(2) groups. The C=O and O-H bonds of the acid group are in syn positions with respect to each other. In the crystal, the mol-ecules are packed into infinite chains along the a axis through inter-molecular N-H⋯O and O-H⋯O hydrogen bonds.

Methyl N-(2,3-dichloro-phen-yl)succinamate.

The asymmetric unit of the title compound, C(11)H(11)Cl(2)NO(3), contains two independent mol-ecules. In both the molecules, the H atoms of the adjacent -CH(2) groups of the acid segments orient themselves away from the amide O and the carbonyl O atoms. The C=O and O-CH(3) bonds of the ester group are in syn positions with respect to each other. In the crystal, the mol-ecules are linked into infinite chains through inter-molecular N-H⋯O hydrogen bonds.

N-(3-Methyl-phen-yl)succinimide.

In the title compound, C(11)H(11)NO(2), the dihedral angle between the ring planes is 52.5 (1)°.

N-(2,6-Dimethyl-phen-yl)succinimide.

The mol-ecule of the title compound, C(12)H(13)NO(2), lies on a twofold rotation axis that passes through the N and C(para) atoms as well as through the mid-point of the bond between the methyl-ene C atoms. The dihedral angle between the aromatic ring and the amide segment is 75.9 (1)°.

Methyl 3-[(3,5-dichloro-anilino)carbon-yl]propionate.

In the title compound, C(11)H(11)Cl(2)NO(3), the amide O atom and the carbonyl O atom of the ester segment are anti to each other and anti to the H atoms of the adjacent -CH(2) groups. In the crystal structure, mol-ecules are packed into centrosymmetric dimers through inter-molecular N-H⋯O hydrogen bonds. The dimers are linked into a layer structure extending parallel to (02) by C-H⋯O hydrogen bonds.

N-(4-Methyl-phen-yl)succinimide.

In the mol-ecule of the title compound, C(11)H(11)NO(2), the dihedral angle between the aromatic ring and the amide segment is 57.3 (1)°.