Crystal structure of 2-[2-(2,5-di-chloro-benz-yloxy)-2-(furan-2-yl)eth-yl]-2H-indazole.

In the title compound, C20H16Cl2N2O2, the indazole ring system is approximately planar [maximum deviation = 0.033 (1) Å], its mean plane is oriented at dihedral angles of 25.04 (4) and 5.10 (4)° to the furan and benzene rings, respectively. In the crystal, pairs of C-Hind⋯Obo (ind = indazole and bo = benz-yloxy) hydrogen bonds link the mol-ecules into centrosymmetric dimers with graph-set motif R22(12). Weak C-H⋯π inter-actions is also observed. Aromatic π-π stacking between the benzene and the pyrazole rings from neighbouring mol-ecules [centroid-centroid distance = 3.8894 (7) Å] further consolidates the crystal packing.

2-[2-(2,6-Di-chloro-benz-yloxy)-2-phenyl-eth-yl]-2H-indazole.

In the title compound, C22H18Cl2N2O, the indazole ring system is approximately planar [maximum deviation = 0.031 (2) Å], its mean plane is oriented at 3.17 (4) and 19.34 (4)° with respect to the phenyl and benzene rings. In the crystal, weak C-H⋯π inter-actions link the mol-ecules into supra-molecular chains running along the b-axis direction.

1-(Furan-2-yl)-2-(2H-indazol-2-yl)ethanone.

The asymmetric unit of the title compound, C13H10N2O2, contains two crystallographically independent mol-ecules (A and B). The indazole ring systems are approximately planar [maximum deviations = 0.0037 (15) and -0.0198 (15) Å], and their mean planes are oriented at 80.10 (5) and 65.97 (4)° with respect to the furan rings in mol-ecules A and B, respectively. In the crystal, pairs of C-H⋯N hydrogen bonds link the B mol-ecules, forming inversion dimers. These dimers are bridged by the A mol-ecules via C-H⋯O hydrogen bonds, forming sheets parallel to (011). There are also C-H⋯π inter-actions present, and π-π inter-actions between neighbouring furan and the indazole rings [centroid-centroid distance = 3.8708 (9) Å] of inversion-related mol-ecules, forming a three-dimensional structure.

1-{2-Benz-yloxy-2-[4-(morpholin-4-yl)phen-yl]eth-yl}-1H-benzimidazole.

In the title compound, C26H27N3O2, the morpholine ring adopts a chair conformation. The benzene and phenyl rings are inclined to the benzimidazole mean plane by 7.28 (6) and 61.45 (4)°, respectively. In the crystal, pairs of weak C-H⋯O hydrogen bonds link the mol-ecules into inversion dimers. These dimers are further connected via weak C-H⋯N hydrogen bonds. A weak C-H⋯π inter-action is also observed.

2-(2H-Indazol-2-yl)-1-phenyl-ethanone.

The asymmetric unit of the title compound, C(15)H(12)N(2)O, contains two independent mol-ecules with different conformations, the phenyl ring and indazole mean plane in the two mol-ecules forming dihedral angles of 50.82 (5) and 89.29 (6)°. In the crystal, weak C-H⋯O and C-H⋯N hydrogen bonds and C-H⋯π inter-actions consolidate the packing.

1-{2-(4-Chloro-benz-yloxy)-2-[4-(mor-pho-lin-4-yl)phen-yl]eth-yl}-1H-benzimidazole propan-2-ol monosolvate.

In the title compound, C26H26ClN3O2·C3H7OH, the benzimid-azole ring system is essentially planar [maximum deviation = -0.018 (2) Å] and its mean plane is oriented with respect to the two benzene rings at dihedral angles of 4.51 (6) and 56.16 (6)°, and the dihedral angle between the two benzene rings is 59.11 (7)°. The morpholine ring displays a chair conformation. The propan-2-ol solvent mol-ecule links with the benzimidazole ring via an O-H⋯N hydrogen bond. In the crystal, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into inversion dimers with an R 2 (2)(28) motif. π-π stacking occurs between the parallel chloro-benzene rings [centroid-centroid distance = 3.792 (1) Å]. Weak C-H⋯π inter-actions and short Cl⋯Cl [3.2037 (10) Å] contacts are also observed.

1-[2-(2,4-Dichloro-benz-yloxy)-2-(furan-2-yl)eth-yl]-1H-benzotriazole.

In the title compound, C(19)H(15)Cl(2)N(3)O(2), the benzotriazole ring system is approximately planar [maximum deviation = 0.018 (2) Å] and its mean plane is oriented at dihedral angles of 30.70 (5) and 87.38 (4)°, respectively, to the furan and benzene rings while the dihedral angle between furan and benzene rings is 74.46 (6)°. In the crystal, weak C-H⋯N hydrogen bonds link the mol-ecules into chains along the b axis. π-π stacking inter-actions between the parallel dichloro-benzene rings of adjacent mol-ecules [centroid-centroid distance = 3.6847 (9) Å] and weak C-H⋯π inter-actions are also observed.

2-(1H-Benzotriazol-1-yl)-1-(furan-2-yl)ethanol.

In the title compound, C(12)H(11)N(3)O(2), the benzotriazole ring system is approximately planar [maximum deviation = 0.008 (1) Å] and its mean plane is oriented at a dihedral angle of 24.05 (4)° with respect to the furan ring. In the crystal, O-H⋯N hydrogen bonds link the mol-ecules into chains along the ac diagonal. π-π stacking between the furan rings, between the triazole and benzene rings, and between the benzene rings [centroid-centroid distances = 3.724 (1), 3.786 (1) and 3.8623 (9) Å] are also observed.

1-[2-(2,5-Dichloro-benz-yloxy)-2-phenyl-eth-yl]-1H-benzotriazole.

In the title mol-ecule, C(21)H(17)Cl(2)N(3)O, the benzotriazole ring is oriented at dihedral angles of 48.72 (6) and 62.94 (5)°, respectively, to the phenyl and benzene rings and the dihedral angle between the phenyl and benzene rings is 88.95 (6)°. In the crystal, weak C-H⋯N hydrogen bonds link the mol-ecules into chains. π-π contacts between the triazole and benzene rings [centroid-centroid distance = 3.678 (1) Å] and a weak C-H⋯π inter-action are also observed.

2-(1H-Benzotriazol-1-yl)-3-(2,6-dichloro-phen-yl)-1-phenyl-propan-1-ol.

The asymmetric unit of the title compound, C(21)H(17)Cl(2)N(3)O, contains two crystallographically independent mol-ecules with similar conformations. The benzotriazole ring is oriented at dihedral angles of 30.61 (5) and 43.36 (5)°, respectively, to the phenyl and dichloro-phenyl rings in one mol-ecule, and 32.25 (5) and 41.04 (5)° in the other. The dihedral angles between the phenyl and dichloro-phenyl rings are 66.38 (7) and 66.14 (6)° in the two mol-ecules. An intra-molecular O-H⋯N hydrogen bond links the benzotriazole ring and phenyl-propanol unit in each mol-ecule. In the crystal, weak inter-molecular C-H⋯N hydrogen bonds link the mol-ecules into chains along the a axis. π-π stacking between the dichloro-phenyl rings [centroid-centroid distances = 3.809 (1) and 3.735 (1) Å] may further stabilize the crystal structure.

1-[2-(4-Chloro-benz-yloxy)-2-phenyl-ethyl]-1H-benzotriazole.

The asymmetric unit of the title compound, C(21)H(18)ClN(3)O, contains two crystallographically independent mol-ecules which differ slightly in the orientations of chloro-benz-yloxy units. In one of the mol-ecules, the phenyl and chloro-phenyl rings are oriented at dihedral angles of 38.09 (6) and 42.15 (6)°, respectively, with respect to the benzotriazole ring [43.23 (6) and 29.80 (6)° in the other mol-ecule]. The dihedral angle between the phenyl and chloro-phenyl rings is 77.63 (6)° in one of the mol-ecules and 72.97 (6)° in the other. The crystal structure is stabilized by weak C-H⋯π inter-actions.

2-(1H-Benzotriazol-1-yl)-1-phenyl-ethanol.

In the title compound, C(14)H(13)N(3)O, the benzotriazole ring is oriented at a dihedral angle of 13.43 (4)° with respect to the phenyl ring. In the crystal structure, inter-molecular O-H⋯N hydrogen bonds link the mol-ecules into chains along the b axis. Aromatic π-π contacts between benzene rings and between triazole and benzene rings [centroid-centroid distances = 3.8133 (8) and 3.7810 (8) Å, respectively], as well as a weak C-H⋯π inter-action involving the phenyl ring, are also observed.

1-[2-(2,4-Dichloro-benz-yloxy)-2-(2-fur-yl)eth-yl]-1H-1,2,4-triazole.

In the mol-ecule of the title compound, C(15)H(13)Cl(2)N(3)O(2), the triazole ring is oriented at dihedral angles of 14.8 (2) and 81.5 (1)° to the furan and dichloro-benzene rings, respectively. The dihedral angle between the dichloro-benzene and furan rings is 86.3 (2)°. An intra-molecular C-H⋯O hydrogen bond results in the formation of a planar [maximum deviation 0.012 (2) Å] five-membered ring, which is oriented at a dihedral angle of 0.90 (7)° with respect to the dichloro-benzene ring. There is an inter-molecular C-H⋯π contact between the methyl-ene group and the dichloro-benzene ring.

1-[2-(2,6-Dichloro-benz-yloxy)-2-(2-fur-yl)eth-yl]-1H-1,2,4-triazole.

In the mol-ecule of the title compound, C(15)H(13)Cl(2)N(3)O(2), the triazole ring is oriented at dihedral angles of 2.54 (13) and 44.43 (12)°, respectively with respect to the furan and dichloro-benzene rings. The dihedral angle between the dichloro-benzene and furan rings is 46.75 (12)°. In the crystal structure, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric dimers and π-π contacts between dichloro-benzene rings [centroid-centroid distance = 3.583 (2) Å] may further stabilize the structure. Inter-molecular C-H⋯π contacts between the triazole and furan rings also occur.

2-(1H-Benzimidazol-1-yl)-1-(2-furyl)ethanone O-propyloxime.

In the mol-ecule of the title compound, C(16)H(17)N(3)O(2), the planar benzimidazole ring system [maximum deviation = 0.013 (1) Å] is oriented at a dihedral angle of 75.32 (4)° with respect to the furan ring. An intra-molecular C-H⋯O inter-action results in the formation of a planar six-membered ring [maximum deviation = 0.019 (15) Å], which is oriented at a dihedral angle of 1.91 (3)° with respect to the adjacent furan ring. In the crystal structure, inter-molecular C-H⋯N inter-actions link the mol-ecules into centrosymmetric R(2) (2)(18) dimers. In addition, the structure is stabilized by π-π contacts between the imidazole rings [centroid-centroid distance = 3.5307 (8) Å] and weak C-H⋯π inter-actions.

2-(1H-Benzimidazol-1-yl)-1-(2-fur-yl)ethanone O-isopropyl-oxime.

In the mol-ecule of the title compound, C(16)H(17)N(3)O(2), the planar benzimidazole ring system [maximum deviation = 0.015 (2) Å] is oriented at a dihedral angle of 72.17 (4)° with respect to the furan ring. An intra-molecular C-H⋯O inter-action results in the formation of a six-membered ring having an envelope conformation. In the crystal structure, inter-molecular C-H⋯N inter-actions link the mol-ecules into centrosymmetric R(2) (2)(18) dimers.

2-(1H-Benzimidazol-1-yl)-1-(2-fur-yl)ethanone O-ethyl-oxime.

In the mol-ecule of the title compound, C(15)H(15)N(3)O(2), the planar benzimidazole ring system [maximum deviation = 0.023 (2) Å] is oriented at a dihedral angle of 74.21 (5)° with respect to the furan ring. In the crystal structure, inter-molecular C-H⋯N inter-actions link the mol-ecules into centrosymmetric R(2) (2)(18) dimers. In addition, the structure is stabilized by π-π contacts between parallel imidazole rings [centroid-centroid distance = 3.726 (1) Å] and a weak C-H⋯π inter-action.

1-[2-(4-Bromo-benz-yloxy)-2-phenyl-ethyl]-1H-1,2,4-triazole.

In the mol-ecule of the title compound, C(17)H(16)BrN(3)O, the triazole ring is oriented at dihedral angles of 6.14 (9)° and 82.08 (9)°, respectively, with respect to the phenyl and bromo-benzene rings. The dihedral angle between the bromo-benzene and phenyl rings is 87.28 (7)°. The intra-molecular C-H⋯O hydrogen bond results in the formation of a planar five-membered ring, which is oriented at a dihedral angle of 0.13 (6)° with respect to the bromo-benzene ring. There is an inter-molecular C-H⋯π contact between a methyl-ene group and the bromo-benzene ring.

1-Phenyl-2-(1H-1,2,4-triazol-1-yl)ethanol.

In the title compound, C(10)H(11)N(3)O, the planar five- and six-membered rings are nearly parallel to each other, making a dihedral angle of 2.52 (5)°. Weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric dimers and strong inter-molecular O-H⋯N hydrogen bonds link the dimers into infinite chains along the b axis.

2-(1H-Benzimidazol-1-yl)-1-phenyl-ethanone.

In the mol-ecule of the title compound, C(15)H(12)N(2)O, the planar benzimidazole system is oriented at a dihedral angle of 80.43 (5)° with respect to the phenyl ring. In the crystal structure, non-classical inter-molecular C-H⋯N and C-H⋯O hydrogen bonds link the mol-ecules into layers parallel to the ab plane.