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5-(1-Benzyl-1H-1,2,3-triazol-4-yl)-2,1,3-benzoxadiazole.

ABSTRACT: In the title compound, C(15)H(11)N(5)O, which was prepared as part of a study to identify fluoro-genic substrates for the Cu-catalysed azide-alkyne cyclo-addition (CuAAC) reaction, the benzoxa-diazole unit and the triazole ring are much more closely coplanar [dihedral angle = 10.92?(7)°] than either is to the benzyl group [dihedral angles = 69.13?(3)° and 78.20?(4)°, respectively]. The crystal structure features two different sets of weak inter-molecular C-H?N inter-actions between adjacent benzoxadiazole and triazole rings, forming a chain that propagates in the [-110] direction parallel to the ab plane.

SUBMITTER: Key JA

PROVIDER: S-EPMC3515234 | biostudies-literature | 2012 Nov

REPOSITORIES: biostudies-literature

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5-(1-Benzyl-1H-1,2,3-triazol-4-yl)-2,1,3-benzoxadiazole.

Key Jessie A JA Cairo Christopher W CW McDonald Robert R

Acta crystallographica. Section E, Structure reports online 20121013 Pt 11

In the title compound, C(15)H(11)N(5)O, which was prepared as part of a study to identify fluoro-genic substrates for the Cu-catalysed azide-alkyne cyclo-addition (CuAAC) reaction, the benzoxa-diazole unit and the triazole ring are much more closely coplanar [dihedral angle = 10.92 (7)°] than either is to the benzyl group [dihedral angles = 69.13 (3)° and 78.20 (4)°, respectively]. The crystal structure features two different sets of weak inter-molecular C-H⋯N inter-actions between adjacent benz ...[more]

PMID: 23284454

Similar Datasets

5-(4-Hexyl-1H-1,2,3-triazol-1-yl)-2,1,3-benzoxadiazole.

Project description:The title compound, C(14)H(17)N(5)O, a 1,2,3-triazole derivative of benzoxadiazole (C(14)H(17)N(5)O), was synthesized via Cu-catal-ysed azide-alkyne cyclo-addition (CuAAC) from the corres-ponding n-octyne and 4-azido-benzoxadiazole. The benz-oxa-diazole and triazole rings show a roughly planar orientation [dihedral angle between the ring planes = 12.18?(5)°]. The alkane chain adopts a zigzag conformation, which deviates from the central triazole ring by 20.89?(6)°. These two torsion angles result in an overall twist to the structure, with a dihedral angle of 32.86?(7)° between the benzoxadiazole group and the hexyl chain. The crystal structure features C-H?N hydrogen bonds leading to chains propagating along [2-10] and offset parallel stacking inter-actions of the triazole and benzoxadiazole rings. The centroid of the extended ?-system formed by the benzoxadiazole and triazole rings (14 atoms total) was calculated; the centroid-centroid distance was 4.179?Å, interplanar separation was 3.243?Å, and the resulting offset was 2.636?Å.

| S-EPMC3515233 | biostudies-literature

1-[1-(2,1,3-Benzoxadiazol-5-ylmeth-yl)-1H-1,2,3-triazol-4-yl]hexan-1-one.

Project description:The title compound, C(15)H(17)N(5)O(2), was synthesized as part of a series of benzoxadiazole analogs which were examined for fluorescent properties by Cu-catalysed azide-alkyne cyclo-addition (CuAAC) of a 4-azido-methyl-benzoxadiazole substrate. The structure shows a nearly coplanar orientation of the hexa-none keto group and the 1,2,3-triazole ring [dihedral angle = 4.3?(3)°], while the benzoxadiazole and triazole groups are much more severely inclined [dihedral angle = 70.87?(4)°]. In the crystal, weak C-H?N inter-actions connect translationally-related triazole rings, while another set of C-H?N inter-actions is formed between inversion-related benzoxadiazole units, forming a three-dimensional network. The crystal studied was a non-merohedral twin with refined value of the twin fraction of 0.2289?(16).

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5-[(4-Benzyl-1H-1,2,3-triazol-1-yl)meth-yl]-5H-dibenzo[b,f]azepine.

Project description:In the title compound, C24H20N4, the azepine ring adopts a boat conformation and the dihedral angle between the benzene rings fused to it is 57.95?(8)°. The bond-angle sum at the azepine N atom is 346.6°, indicating a significant deviation from planarity. The triazole ring subtends a dihedral angle of 71.45?(10)° with the terminal phenyl group. A weak intra-molecular C-H?Na (a = azepine) inter-action occurs, which closes an S(6) ring.

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3-Benzyl-sulfanyl-5-(4-phenyl-1H-1,2,3-triazol-1-ylmeth-yl)-4H-1,2,4-triazol-4-amine.

Project description:The mol-ecule of the title compound, C(18)H(17)N(7)S, is non-planar, with a dihedral angle of 71.4?(4)° between the two triazole rings, and an angle of 15.5?(3)° between the two phenyl rings. An intra-molecular N-H?S hydrogen bond forms a five-membered ring.

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3-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methyl]-1,5-dimethyl-1,5-benzodiazepine-2,4-dione.

Project description:The title compound, C(21)H(21)N(5)O(2), is a 1,4-dimethyl-1,2,3-triazole having dimethyl-benzodiazepindione and phenyl substituents on each methyl group; the substituents are positioned on opposite sides of the five-membered ring. The seven-membered fused-ring of the larger substituent adopts a boat-shaped conformation (with the methine C atom as the prow).

| S-EPMC2983517 | biostudies-literature

3-[(1-Benzyl-1H-1,2,3-triazol-5-yl)methyl]-1,5-dimethyl-1,5-benzodiazepine-2,4-dione monohydrate.

Project description:In the title compound, C(21)H(21)N(5)O(2)·H(2)O, the seven-membered ring adopts a boat-shaped conformation with the methine C atom as the prow. In the crystal, the water mol-ecule links adjacent mol-ecules by O-H?O and O-H?N hydrogen bonds into a zigzag chain running along the c axis of the monoclinic cell.

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(E)-Benz-yl(4-{[1-(prop-2-en-1-yl)-1H-1,2,3-triazol-4-yl]meth-oxy}benzyl-idene)amine.

Project description:The triazole ring of the title compound, C20H20N4O, is normal to the central benzene ring, making a dihedral angle of 90.0?(3)°, and forms a dihedral angle of 69.2?(3)° with the terminal phenyl ring. The dihedral angle between the phenyl and benzene rings is 88.2?(3)°. The atoms of the terminal propenyl group are disordered over two sets of sites, with a site-occupancy ratio of 0.663?(13):0.337?(13). In the crystal, C-H?N contacts lead to the formation of a layer structure extending parallel to (011). Two weak C-H?? inter-actions are also observed.

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3-[(1-Benzyl-1H-1,2,3-triazol-5-yl)meth-yl]-6-bromo-2-phenyl-3H-imidazo[4,5-b]pyridine.

Project description:There are two crystallographically independent mol-ecules in the asymmetric unit of the title compound, C(22)H(17)BrN(6). The dihedral angles between the imidazo[4,5-b]pyridine mean plane and the phenyl rings are 20.4 (2) and 24.0 (2)° in the two mol-ecules. The orientation of triazoles compared to the imidazo[4,5-b]pyridine system is almost the same in both mol-ecules, with dihedral angles of 64.2 (2) and 65.1 (2)°. However, the main difference between the two mol-ecules lies in the arrangement of the phenyl groups compared to imidazo[4,5-b]pyridine in each mol-ecule. Indeed, in the first mol-ecule the dihedral angle between the plane of the phenyl ring and that of the imidazo[4,5-b]pyridine system is 67.7 (2)°, while in the second mol-ecule the plane of the phenyl ring is almost perpendicular to that of the imidazo[4,5-b]pyridine system with a dihedral angle of 86.0 (2)°.

| S-EPMC3099998 | biostudies-literature

[1-(3-Chloro-phen-yl)-1H-1,2,3-triazol-4-yl]methanol hemihydrate.

Project description:The asymmetric unit of the title hydrate, C(9)H(8)ClN(3)O·0.5H(2)O, comprises two independent 1,2,3-triazole mol-ecules and a water mol-ecule of crystallization. The dihedral angles between the six- and five-membered rings in the 1,2,3-triazole mol-ecules are 12.71?(19) and 17.3?(2)°. The most significant different between them is found in the relative orientations of the terminal CH(2)OH groups with one being close to perpendicular to the five-membered ring [N-C-C-O torsion angle = 82.2?(5)°], while in the other mol-ecule, a notable deviation from a perpendicular disposition is found [torsion angle = -60.3?(5)°]. Supra-molecular chains feature in the crystal packing sustained by O-H?(O,N) inter-actions along the a-axis direction. The chains are connected via C-H?N inter-actions and the resultant layers stack along the b axis.

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