Benzotriazole Ring System Research Articles

1H-Benzotriazole–4-hydroxybenzoic acid (1/1)

The asymmetric unit of the title compound, C6H5N3·C7H6O3, comprises independent benzotriazole and 4-hydroxybenzoic acid molecules. The dihedral angle between the benzene ring and the benzotriazole ring system is 15.18 (7)°. The mean plane of the carb­oxyl group is twisted at an angle of 18.55 (1)° with respect to the benzene ring. The crystal structure is stabilized by weak inter­molecular N—H⋯N, O—H⋯N, O—H⋯O and C—H⋯O inter­actions, forming a three-dimensional network.

1-Benzyl-1H-benzotriazole 3-oxide monohydrate.

In the title hydrate, C13H11N3O·H2O, the benzotriazole ring system is planar (r.m.s. deviation = 0.007 Å) and is almost orthogonal to the phenyl ring to which it is linked by a methyl­ene group, forming a dihedral angle of 81.87 (15)°. In the crystal, mol­ecules are linked into chains along [001] by O—H⋯O hydrogen bonds. The chains are consolidated into a three-dimensional architecture by C—H⋯O, C—H⋯π and π–π [centroid–centroid distance between the five- and six-membered rings of the benzotriazole ring system = 3.595 (3) Å] inter­actions.

1-(1H-1,2,3-Benzotriazol-1-yl)-2-(4-methoxyphenyl)ethanone

In the title compound, C15H13N3O2, the dihedral angle between the benzotriazole ring system (r.m.s. deviation = 0.0124 Å) and the benzene ring is 76.21 (3)°. The meth­oxy C atom deviates from its benzene ring plane by 0.063 (2)Å. In the crystal, inversion dimers linked by pairs of C—H⋯O hydrogen bonds generate R 2 2(12) loops.

2-(2H-Benzotriazol-2-yl)-6-[(dicyclohexylamino)methyl]-4-(2,4,4-trimethylpentan-2-yl)phenol

In the title mol­ecule, C33H48N4O, the dihedral angle between the mean planes of the benzotriazole ring system [maximun deviation = 0.038 (2) Å] and the phenol ring is 16.6 (2)°. There is an intra­molecular O—H⋯N hydrogen bond between the phenol and benzotriazole groups.

1-Benzyl-1H-benzotriazole 3-oxide–1-hydroxy-1H-benzotriazole (1/1)

In the title compound, C6H5N3O·C13H11N3O, the benzo­triazole ring system in the 1-benzyl-1H-benzotriazole 3-oxide (A) mol­ecule is close to being planar (r.m.s. deviation = 0.011 Å); its mean plane forms a dihedral angle of 67.56 (7)° with that of the attached phenyl ring. The benzotriazole ring system in the 1-hy­droxy­benzotriazole (B) mol­ecule is also close to being planar (r.m.s. deviation = 0.010 Å). In the crystal, weak C—H⋯O and C—H⋯π inter­actions are present. The A and B molecules are linked by an O—H⋯N hydrogen bond.

1-Benzyloxy-1H-benzotriazole

In the title compound, C13H11N3O, the dihedral angle between the benzotriazole ring system [maximum deviation = 0.027 (16) Å] and the benzene ring is 10.28 (9)°. The C—C—O—N bond adopts an anti conformation [torsion angle = −177.11 (16)°]. In the crystal, the mol­ecules inter­act via weak C—H⋯π inter­actions and aromatic π–π stacking [centroid-to-centroid distance = 3.731 (12) Å].

(1H-1,2,3-Benzotriazol-1-yl)methyl benzoate

In the title compound, C14H11N3O2, the dihedral angle between the phenyl ring and the benzotriazole ring system is 76.80 (19)° and the mol­ecule has an L-shaped conformation. In the crystal, weak aromatic π–π stacking is observed, the closest centroid–centroid distance being 3.754 (2) Å.

1-Benzyl-1H-benzotriazole.

In the title compound, C13H11N3, the benzotriazole ring system is essentially planar, with a maximum deviation of 0.0173 (18) Å, and forms a dihedral angle of 75.08 (8)Å with the phenyl ring. In the crystal, pairs of weak C—H⋯N hydrogen bonds form inversion dimers. In addition, there are weak C—H⋯π(arene) inter­actions and weak π–π stacking inter­actions, with a centroid–centroid distance of 3.673 (11) Å.

Bis(μ-trimethylsilanolato-κ2O:O)bis{[2-(2H-benzotriazol-2-yl)-4,6-di-tert-pentylphenolato-κ2N,O]zinc}

The binuclear title complex, [Zn2(C22H28N3O)2(C3H9OSi)2], has a crystallographic imposed centre of symmetry. The ZnII atom is coordinated by three O and one N atom from one 2-(2H-benzotriazol-2-yl)-4,6-di-tert-pentyl­phenolate ligand and two bridging trimethyl­silanolate anions in a distorted tetra­hedral geometry. The dihedral angle between the benzotriazole ring system and the benzene ring is 19.83 (5)°. The tert-pentyl groups are disordered over two orientations with refined site-occupancy ratios of 0.858 (4):0.142 (4) and 0.665 (6):0.335 (6).

1-[2-(2,4-Dichlorobenzyloxy)-2-(furan-2-yl)ethyl]-1H-benzotriazole

In the title compound, C19H15Cl2N3O2, 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 mol­ecules into chains along the b axis. π–π stacking inter­actions between the parallel dichloro­benzene rings of adjacent mol­ecules [centroid–centroid distance = 3.6847 (9) Å] and weak C—H⋯π inter­actions are also observed.

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

In the title compound, C12H11N3O2, 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 mol­ecules 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.

Ethyl 1-[2-(1H-benzotriazol-1-yl)acetyl]-4-hydroxy-2,6-diphenyl-1,2,5,6-tetrahydropyridine-3-carboxylate

In the title compound, C28H26N4O4, the tetra­hydro­pyridine ring adopts a boat conformation. The two phenyl rings form dihedral angles of 88.64 (8) and 59.28 (10)° with the best plane through the tetra­hydro­pyridine ring. The dihedral angle between the two phenyl rings is 82.55 (10)°. The benzotriazole ring system is essentially planar, with a maximum deviation of 0.009 (1) Å from the least-squares plane. The mol­ecular conformation is stabilized by an intra­molecular O—H⋯O hydrogen bond, generating an S(6) motif.

Discovery of Orally Active, Potent, and Selective Benzotriazole‐Based PTP1B Inhibitors

Discovery of Orally Active, Potent, and Selective Benzotriazole‐Based PTP1B Inhibitors

(E)-2-(2H-Benzotriazol-2-yl)-4-methyl-6-(phenyliminomethyl)phenol

In the title compound, C20H16N4O, the non-H atoms of the benzotriazole ring system and those of the methyl­phenol group are essentially coplanar, with an r.m.s. deviation of 0.004 (2) Å. The mean plane of these atoms forms a dihedral angle of 60.9 (2)° with the phenyl ring. There is an intra­molecular O—H⋯N hydrogen bond between the phenol and benzotriazole groups.

2-(2-Methoxy-5-methylphenyl)-2H-benzotriazole

In the title mol­ecule, C14H13N3O, the dihedral angle between the mean planes of the benzotriazole ring system and the benzene ring is 57.8 (2)°.

3-(2H-Benzotriazol-2-yl)-1-(4-fluorophenyl)propan-1-one

In the title compound, C15H12FN3O, the benzotriazole ring system is essentially planar, with a maximum deviation from the least-squares plane of 0.016 (3) Å. The dihedral angle between this ring system and the fluoro-substituted benzene ring is 67.97 (2)°. The crystal structure is stabilized by weak inter­molecular C—H⋯N inter­actions.

3-(2H-Benzotriazol-2-yl)-2-hydroxy-5-methylbenzaldehyde

In the title compound, C14H11N3O2, the dihedral angle between the mean planes of the benzotriazole ring system and the benzene ring of the salicylaldehyde group is 2.4 (2)°. There is an intra­molecular O—H⋯N hydrogen bond which may influence the mol­ecular conformation.

2-(1H-Benzotriazol-1-yl)-1-(3-methylbenzoyl)ethyl benzoate

In the title mol­ecule, C23H19N3O3, the dihedral angles between the mean plane of the benzotriazole ring system and the benzene and phenyl rings are 9.67 (9) and 86.08 (10)°, respectively. The dihedral angle between the benzene and phenyl rings is 85.89 (11)°. In the crystal structure, weak inter­molecular C—H⋯O hydrogen bonds link mol­ecules into chains along [010].

2-(1H-Benzotriazol-1-yl)-1-(4-bromobenzoyl)ethyl 2-chlorobenzoate

In the title compound, C22H15BrClN3O3, the benzotriazole ring system makes dihedral angles of 2.43 (1) and 71.51 (1)° with the bromo­phenyl and chloro­phenyl rings, respectively; the angle between the latter two rings is 69.26 (1)°. In the crystal structure, mol­ecules are linked into chains by inter­molecular C—H⋯O hydrogen bonds. The crystal packing is further stabilized by π–π (with a centroid-centroid distance of 3.764 Å) and C—H⋯π inter­actions.

3-(1H-Benzotriazol-1-yl)-2-bromo-1-o-tolylpropan-1-one

In the mol­ecule of the title compound, C16H14BrN3O, the benzotriazole ring system makes a dihedral angle of 62.1 (1)° with the benzene ring of the tolyl group. Weak π–π stacking inter­actions are observed between the triazole rings of inversion-related molecules, with a centroid–centroid distance of 3.726 (1) Å.