Browse
Submit Data
Databases
API
Help

Dataset Information

18 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

6-Chloro-3-(3-methyl-phen-yl)-1,2,4-triazolo[4,3-b]pyridazine.

ABSTRACT: The title compound, C(12)H(9)ClN(4), was prepared from dichloro-pyridazine and tolyl-tetra-zole in a nucleophilic biaryl coupling followed by thermal ring transformation. The mol-ecule is essentially planar (r.m.s. deviation for all non-H atoms = 0.036?Å) and an intra-molecular C-H?N hydrogen bond occurs. In the crystal, the mol-ecules form dimers connected via ?-? inter-actions [centroid-centroid distance = 3.699?(2)?Å], which are further connected to neighbouring mol-ecules via C-H-N bonds. The bond lengths in the pyridazine ring system indicate a strong localization of the double bonds and there is a weak C-Cl bond [1.732?(3)?Å].

SUBMITTER: Preis J

PROVIDER: S-EPMC3201469 | biostudies-literature | 2011 Oct

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

6-Chloro-3-(3-methyl-phen-yl)-1,2,4-triazolo[4,3-b]pyridazine.

Preis Jasmin J Schollmeyer Dieter D Detert Heiner H

Acta crystallographica. Section E, Structure reports online 20110903 Pt 10

The title compound, C(12)H(9)ClN(4), was prepared from dichloro-pyridazine and tolyl-tetra-zole in a nucleophilic biaryl coupling followed by thermal ring transformation. The mol-ecule is essentially planar (r.m.s. deviation for all non-H atoms = 0.036 Å) and an intra-molecular C-H⋯N hydrogen bond occurs. In the crystal, the mol-ecules form dimers connected via π-π inter-actions [centroid-centroid distance = 3.699 (2) Å], which are further connected to neighbouring mol-ecules via C-H-N bonds. Th ...[more]

PMID: 22058729

Similar Datasets

5-Methyl-3-(3-methyl-phen-yl)-7-phenyl-1,2,4-triazolo[4,3-c]pyrimidine.

Project description:The title compound, C(19)H(16)N(4), is one of the few known 3,7-diaryl-1,2,4-triazolo[4,3-c]pyrimidines. The triazolopyrimidine unit is essentially planar (r.m.s. deviation = 0.048?Å). The phenyl ring and the heterocyclic core subtend a dihedral angle of only 15.09?(6)°, whereas the m-tolyl ring is twisted by 71.80?(6)° out of the plane of the triazole ring. Two C-H?N hydrogen bonds and ?-? stacking inter-actions [centroid-centroid distance = 3.7045?(8)?Å] stabilize the crystal packing.

| S-EPMC3099827 | biostudies-other

Ethyl 8-(2,4-di-chloro-phen-yl)-6-methyl-1,2,4-triazolo[1,5-a]pyridine-7-carboxyl-ate.

Project description:In the title compound, C16H13Cl2N3O2, the carboxyl-ate group and the benzene ring attached to the central 1,2,4-triazolo[1,5-a]pyridine bicycle are twisted from its mean plane by 55.6?(1) and 72.6?(1)°, respectively. In the crystal, weak C-H?O inter-actions link the mol-ecules into zigzag chains propagating in [100].

| S-EPMC3885057 | biostudies-literature

8-Methyl-2-[4-(trifluoro-meth-yl)phen-yl]-8H-pyrazolo-[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine methanol disolvate.

Project description:In the title compound, C(14)H(10)F(3)N(7)·2CH(4)O, the heterocyclic ring system is essentially planar (r.m.s. deviation = 0.009?Å) and makes a dihedral angle of 6.91?(8)° with the attached benzene ring. In the crystal, the main mol-ecules form centrosymmetric R(2) (2)(8) dimers via pairs of N-H?N hydrogen bonds between the amino groups and pyrimidine N atoms. One of the independent methanol mol-ecules and its inversion equivalent are linked to the dimers via O-H?N and N-H?O hydrogen bonds, forming R(4) (4)(16) graph-set motifs. The dimers along with the hydrogen-bonded methanol mol-ecules are stacked along the a axis, with ?-? inter-actions between the pyrazole and triazole rings [centroid-centroid distance = 3.4953?(10)?Å].

| S-EPMC3007048 | biostudies-literature

3-(4-Chloro-phen-yl)-5-phenyl-1,2,4-triazolo[3,4-a]isoquinoline.

Project description:In the title mol-ecule, C(22)H(14)ClN(3), the triazoloisoquinoline ring system is approximately planar, with an r.m.s. deviation of 0.033?(2)?Å and a maximum departure from the mean plane of 0.062?(1)?Å for the triazole ring C atom, bonded to the benzene ring. The benzene and phenyl rings are twisted by 57.02?(6) and 62.16?(6)°, respectively, to the mean plane of the triazoloisoquinoline ring system. The mol-ecule is stabilized by a weak intra-molecular ?-? inter-action [centroid-centroid distance = 3.7089?(10)?Å] between the benzene and phenyl rings. In the crystal structure, weak inter-molecular C-H?N hydrogen bonds and C-H?? inter-actions link the mol-ecules.

| S-EPMC2979237 | biostudies-literature

5-(4-Chloro-phen-yl)-3-(2-fur-yl)-1,2,4-triazolo[3,4-a]isoquinoline.

Project description:In the title mol-ecule, C(20)H(12)ClN(3)O, the triazoloisoquinoline ring system is nearly planar, with an r.m.s. deviation of 0.018?(3)?Å and a maximum deviation of 0.034?(3)?Å from the mean plane for the triazole ring C atom which is bonded to the benzene ring. The furan and benzene rings are twisted by 59.71?(14) and 66.95?(10)°, respectively, with respect to the mean plane of the triazoloisoquinoline ring system. The mol-ecular conformation is stabilized by an intra-molecular ?-? inter-action [centroid-to-centroid distance = 3.5262?(18)?Å]. The crystal packing is stabilized by weak C-H?? inter-actions and weak ?-? inter-actions [centroid-to-centroid distance = 3.9431?(17)?Å].

| S-EPMC2979100 | biostudies-literature

Crystal structure of 11-[4-(hex-yloxy)phen-yl]-1,2,4-triazolo[4,3-a][1,10]phenanthroline.

Project description:The title compound, C25H24N4O, was prepared from 2-chloro-phenanthroline and hexyl-oxyphenyl-tetra-zole. The main difference between the two independent mol-ecules (A and B) in the asymmetric unit is the orientation of the all-anti-configured hex-yloxy chain: in A the C-O-C-C torsion angle is 175.9 (2)° whereas it is -88.3 (3)° in B. The benzene substitution in the bay of the triazolophenanthroline results in a helical distorsion of the heterocyclic core, the dihedral angles between the mean planes formed by quinoline and benzotriazole ring systems are 13.73 (9) for mol-ecule A and 14.87 (8)° for B. The dihedral angles between the triazole ring and the attached benzene ring are 45.87 (15) in A and 53.93 (14)° in B. The angular annulation of four rings and the benzene substituent results in a helical distortion of the aromatic framework. The crystal is formed from layers composed of centrosymmetric pairs of A 2, B 2 mol-ecules with inter-digitating alkyl chains.

| S-EPMC4518990 | biostudies-literature

2-(2-Chloro-pyrimidin-4-yl)-3,5,6,7,8,9-hexahydro-2H-1,2,4-triazolo[4,3-a]azepin-3-one.

Project description:In the title compound, C(11)H(12)ClN(5)O, the triazolone and pyrimidine rings are almost coplanar [dihedral angle = 2.98?(14)°]. The total puckering amplitude Q(T) of the seven-membered lactam ring is 0.706?(3)?Å.

| S-EPMC2959440 | biostudies-literature

6-(4-Methyl-phen-yl)-3-(3,4,5-trimethoxy-phen-yl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole.

Project description:In the mol-ecule of the title compound, C(19)H(18)N(4)O(3)S, the central heterocylic ring system is oriented with respect to the trimethoxy-phenyl and 4-methyl-phenyl rings at dihedral angles of 1.1?(5) and 15.1?(5)°, respectively. The dihedral angle between the two benzene rings is 16.1?(4)°. In the crystal structure, mol-ecules are linked by inter-molecular C-H?O hydrogen bonds, and an intra-molecular C-H?N inter-action also occurs.

| S-EPMC2959370 | biostudies-literature

6-(2-Methyl-phen-yl)-3-(3,4,5-trimethoxy-phen-yl)-1,2,4-triazolo[3,4-b][1,3,4]thia-diazole.

Project description:In the mol-ecule of the title compound, C(19)H(18)N(4)O(3)S, the planar central heterocylic ring system is oriented with respect to the trimethoxy-phenyl and 2-methyl-phenyl rings at dihedral angles of 4.43?(3) and 4.32?(3)°, respectively. The dihedral angle between the two benzene rings is 7.65?(4)°. In the crystal structure, inter-molecular C-H?N hydrogen bonds link the mol-ecules into centrosymmetric R(2) (2)(18) dimers. These dimers are connected via a C-H?? contact between the 2-methyl-phenyl and trimethoxy-phenyl rings, and a ?-? contact between the thia-diazole and trimethoxy-phenyl rings [interplanar distance 3.51?Å, dihedral angles 4.17(4)°]. An intramolecular C-H?N hydrogen bond is also present.

| S-EPMC2962111 | biostudies-literature

5-(4-Chloro-phen-yl)-3-(2,4-dimethyl-thiazol-5-yl)-1,2,4-triazolo[3,4-a]isoquinoline.

Project description:In the title mol-ecule, C(21)H(15)ClN(4)S, the triazoloisoquinoline ring system is approximately planar, with an r.m.s. deviation of 0.054?(2)?Å and a maximum deviation of 0.098?(2)?Å from the mean plane for the triazole ring C atom that is bonded to the thia-zole ring. The thia-zole and benzene rings are twisted by 66.36?(7) and 56.32?(7)°, respectively, with respect to the mean plane of the triazoloisoquinoline ring system. In the crystal structure, mol-ecules are linked by inter-molecular C-H?N inter-actions along the a axis. The mol-ecular conformation is stabilized by a weak intra-molecular ?-? inter-action involving the thia-zole and benzene rings, with a centroid-centroid distance of 3.6546?(11)?Å. In addition, two other intermolecular ?-? stacking inter-actions are observed, between the triazole and benzene rings and between the dihydro-pyridine and benzene rings [centroid-centroid distances = 3.6489?(11) and 3.5967?(10)?Å, respectively].

| S-EPMC2979146 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data