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In the title compound, C(9)H(6)FNO(2), all the non-H atoms are approximately coplanar, the carb-oxy O atoms deviating by 0.0809 and -0.1279 Å from the indole plane. In the crystal, O-H⋯O hydrogen bonds link the mol-ecules into dimers which are linked via N-H⋯O hydrogen bonds and π-π inter-actions [centroid-centroid distance = 3.680 (2) Å].

The title compound, C(16)H(13)N, is essentially planar [maximum deviation from the least-squares plane = 0.081 (3) Å], with a dihedral angle of 1.65 (13)° between the planes of the indole and benzene rings. In the crystal, there are no significant inter-molecular π-π inter-actions [minimum ring centroid-centroid separation = 4.217 (5) Å].

The title compound, C(10)H(7)ClN(2), contains two approximately planar mol-ecules, A and B (r.m.s. deviations = 0.039 and 0.064 Å, respectively) in the asymmetric unit. In the crystal, N-H⋯N hydrogen bonds link the mol-ecules into C(7) chains of alternating A and B mol-ecules propagating along the a-axis direction. The crystal used for the data collection was found to be a racemic twin.

In the title compound, C(10)H(7)ClN(2), the carbonitrile group is twisted away from the plane of the indole ring system [C(cy)-C(me)-C(ar)-C(ar) = -44.7 (8)°; cy = cyanide, me = methyl-ene and ar = aromatic]. In the crystal, N-H⋯N hydrogen bonds link the mol-ecules into C(7) chains propagating in [010]. Aromatic π-π stacking inter-actions [minimum centroid-centroid separation = 3.663 (3) Å] are also observed.

In the title compound, C(9)H(6)FNO(2), the carboxyl group is twisted slightly away from the indole-ring plane [dihedral angle = 7.39 (10)°]. In the crystal, carboxyl inversion dimers linked by pairs of O-H⋯O hydrogen bonds generate R(2) (2)(8) loops and N-H⋯O hydrogen bonds connect the dimers into (10[Formula: see text]) sheets.

In the title compound, C(11)H(10)N(2)O, the O atom and the C atom of the methyl-ene group deviate only slightly [0.029 (3) and 0.055 (3) Å, respectively] from the approximately planar ring system (r.m.s. deviation = 0.013 Å). In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into zigzag chains running along the b axis.

In the title compound, C(17)H(12)N(2), the inter-planar angle between the indole mean plane [max.deviation 0.030 (1) Å] and the phenyl ring is 24.32 (7)°. In the crystal, inter-molecular N-H⋯N C hydrogen bonds form zigzag chains in the a-axis direction augmented by weak C-H⋯N C contacts.

In the title compound, C(11)H(10)N(2)O, the cyanide group is twisted away from the indole-ring plane [C(cy)-C(me)-C(ar)-C(ar) = 70.7 (2)°; cy = cyanide, me = methyl-ene, ar = aromatic], whereas the meth-oxy C atom is almost coplanar with the ring system [displacement = 0.014 (5) Å]. In the crystal, N-H⋯N hydrogen bonds link the mol-ecules into C(7) chains propagating in [100].

In the title compound, C(11)H(10)N(2), the carbonitrile group is twisted away from the indole plane [C(cy)-C(me)-C(ar)-C(ar) = 66.6 (2)°; cy = cyanide, me = methyl-ene and ar = aromatic]. In the crystal, N-H⋯N hydrogen bonds link the mol-ecules into C(7) chains propagating in the [001] direction.

In the title compound, C(9)H(6)ClNO, the Cl atom deviates by 0.142 (1) Å from the quinoline ring mean plane (r.m.s. deviation = 0.013 Å). In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into [010] C(4) chains. Aromatic π-π stacking inter-actions [shortest centroid⋯centroid distance = 3.685 (3) Å] are also observed.

In the title compound, C(9)H(6)ClNO(2), the carboxyl group is twisted from the indole ring system by 9.00 (8)°. In the crystal, inversion dimers linked by pairs of O-H⋯O hydrogen bonds generate R(2) (2)(8) loops and N-H⋯O hydrogen bonds link the dimers into (001) sheets. Aromatic π-π stacking inter-actions [centroid-centroid distance = 3.7185 (12) A °] are also observed.

In the crystal structure of the title compound, C(8)H(5)NO(6), both carboxyl groups are involved in inter-molecular centrosymmetric cyclic O-H⋯O hydrogen-bonding associations, which give a zigzag chain structure extending along (2[Formula: see text]1). Weak π-π stacking inter-actions are also present [minimum ring centroid separation = 3.893 (4) Å].

In the crystal structure of the title compound, C(5)H(5)NO(3), all the non-H atoms are approximately coplanar: the carb-oxy O atoms deviating by 0.013 (2) and -0.075 (2) Å from the isoxazole ring plane. In the crystal, the molecules form inversion dimers linked by pairs of O-H⋯O hydrogen bonds and the dimers stack via π-π inter-actions [centroid-centroid distance = 3.234 (2) Å].

All non-H atoms of the title compound, C(7)H(7)NO(2), are nearly coplaner, the r.m.s. deviation being 0.0087 Å. In the crystal, the partially overlapped arrangement and the face-to-face distance of 3.466 (17) Å between parallel pyridine rings of neighboring mol-ecules indicates the existence of π-π stacking. Inter-molecular O-H⋯N hydrogen bonding and weak C-H⋯O hydrogen bonding are present in the crystal structure.

In the title compound, [CoCl(2)(C(13)H(20)N(4))]·H(2)O, the Co(II) atom lies on a mirror plane and is four-coordinated by two N atoms of the imidazole ligand and two Cl atoms in a distorted tetra-hedral arrangement. The water mol-ecule participates in the formation of hydrogen bonds, resulting in a three dimensional network involving the Cl atoms and the NH groups. The terminal C atom of the ethyl group is disordered over two sites of equal occupancy.

In the title compound, [Ni(NO(3))(C(13)H(20)N(4))(2)]NO(3), the Ni(II) ion shows a distorted octa-hedral geometry formed by four N atoms from two bis-(2-ethyl-5-methyl-1H-imidazol-4-yl)methane ligands and two O atoms from a chelating nitrate anion. Three ethyl groups in the complex cation and the O atoms of the uncoordinated nitrate anion are disordered over two sets of positions [occupancy ratios of 0.52 (3):0.48 (3) and 0.63 (3):0.37 (3), respectively]. In the crystal, inter-molecular N-H⋯O hydrogen bonds connect the complex cations into a zigzag chain along [010] and further N-H⋯O hydrogen bonds between the chains and the uncoordinated nitrate anions lead to layers parallel to (100).

In the title compound, [Cu(C(2)O(4))(C(13)H(20)N(4))(H(2)O)]·2H(2)O, the Cu(II) atom exhibits a distorted square-pyramidal geometry with the two N atoms of the imidazole ligand and the two O atoms of the oxalate ligand forming the basal plane, while the O atom of the coordinated water mol-ecule is in an apical position. The Cu(II) atom is shifted 0.232 (2) Å out of the basal plane toward the water mol-ecule. The asymmetric unit is completed by two solvent water mol-ecules. These water mol-ecules participate in the formation of an intricate three-dimensionnal network of hydrogen bonds involving the coordinated water mol-ecule and the NH groups.