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Crystal structure and Hirshfeld surface analysis of 5-methyl-1,2,4-triazolo[1,5-a]pyrimidine.

ABSTRACT: The nine-membered ring system of the title compound, C6H6N4, is essentially planar. In the crystal, molecules are linked via C—HTrz?NTrz and C—HPyrm?NTrz (Trz = triazole and Pyrm = pyrimidine) hydrogen bonds together with weaker C—HPyrm?NPyrm hydrogen bonds to form layers parallel to (02). The layers are further connected by ?–?-stacking interactions between the nine-membered ring system [centroid–centroid = 3.7910?(8)?Å], forming oblique stacks along the a-axis direction. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H?N/N?H (40.1%), H?H (35.3%), H?C/C?H (9.5%), N?C/C?N (9.0%), N?N (3.1%) and C?C (3.0%) interactions and that hydrogen-bonding and van der Waals interactions are the dominant interactions in the crystal packing. No significant C—H?? interactions are observed.

SUBMITTER: Lahmidi S

PROVIDER: S-EPMC6281126 | biostudies-other | 2018 Dec

REPOSITORIES: biostudies-other

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Hirshfeld surface analysis and crystal structure of 7-meth-oxy-5-methyl-2-phenyl-11,12-di-hydro-5,11-methano-1,2,4-triazolo[1,5-c][1,3,5]benzoxadiazo-cine.

Project description:The title compound, C19H18N4O2, crystallizes with two independent mol-ecules in the asymmetric unit. The triazole ring is inclined to the benzene rings by 9.63 (13) and 87.37 (12)° in one mol-ecule, and by 4.46 (13) and 86.15 (11)° in the other. In the crystal, classical N-H⋯N hydrogen bonds, weak C-H⋯O hydrogen bonds and weak C-H⋯π inter-actions link the mol-ecules into a three-dimensional supra-molecular network. Hirshfeld surface analysis and two-dimensional fingerprint plots were used to investigate the inter-molecular inter-actions present in the crystal, indicating that the most important contributions for the crystal packing are from H⋯H (51.4%), H⋯C/C⋯H (26.7%), H⋯O/O⋯H (8.9%) and H⋯N/N⋯H (8%) inter-actions.

| S-EPMC6127710 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of two 5,11-methano-benzo[g][1,2,4]triazolo[1,5-c][1,3,5]oxa-diazo-cine derivatives.

Project description:In the title compounds, 9-bromo-2,5-dimethyl-11,12-di-hydro-5H-5,11-methano-benzo[g][1,2,4]triazolo[1,5-c][1,3,5]oxa-diazo-cine, C13H13BrN4O (I), and 7-meth-oxy-5-methyl-2-(pyridin-4-yl)-11,12-di-hydro-5H-5,11-methano-benzo[g][1,2,4]tri-azolo[1,5-c][1,3,5]oxa-diazo-cine, C18H17N5O2 (II), the triazole ring is inclined to the benzene ring by 85.15 (9) and 76.98 (5)° in compounds I and II, respectively. In II, the pyridine ring is almost coplanar with the triazole ring, having a dihedral angle of 4.19 (8)°. In the crystal of I, pairs of N-H⋯N hydrogen bonds link the mol-ecules to form inversion dimers with an R 2 2(8) ring motif. The dimers are linked by C-H⋯π and C-Br⋯π inter-actions forming layers parallel to the bc plane. In the crystal of II, mol-ecules are linked by N-H⋯N and C-H⋯O hydrogen bonds forming chains propagating along the b-axis direction. The inter-molecular inter-actions were investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots, and the mol-ecular electrostatic potential surface was also analysed. The Hirshfeld surface analysis of I suggests that the most significant contributions to the crystal packing are H⋯H (42.4%) and O⋯H/H⋯O (17.9%) contacts. For compound II, the H⋯H (48.5%), C⋯H/H⋯C (19.6%) and N⋯H/H⋯N (16.9%) inter-actions are the most important contributions.

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Crystal structure and Hirshfeld surface analysis of 7-eth-oxy-5-methyl-2-(pyridin-3-yl)-11,12-di-hydro-5,11-methano-[1,2,4]triazolo[1,5-c][1,3,5]benzoxadiazo-cine.

Project description:The title compound, C19H19N5O2, was prepared by the reaction of 3-amino-5-(pyridin-3-yl)-1,2,4-triazole with acetone and 2-hy-droxy-3-eth-oxy-benzaldehyde. It crystallizes from ethanol in a tetra-gonal space group, with one mol-ecule in the asymmetric unit. The 1,2,4-triazole five-membered ring is planar (maximum deviation = 0.0028?Å). The pyridine and phenyl rings are also planar with maximum deviations of 0.0091 and 0.0094?Å, respectively. In the crystal, N-H?N hydrogen bonds link the mol-ecules into supra-molecular chains propagating along the c-axis direction. Hirshfeld surface analysis and two-dimensional fingerprint plots have been used to analyse the inter-molecular inter-actions present in the crystal.

| S-EPMC5947805 | biostudies-other

Crystal structure and Hirshfeld surface analysis of 1,2,4-triazolium hydrogen oxalate.

Project description:The asymmetric unit of the title 1:1 salt 1,2,4-triazolium hydrogen oxalate, C2H4N3 +·C2HO4 - (I), comprises one 1,2,4-triazolium cation and one hydrogen oxalate anion. In the crystal, the hydrogen oxalate anions are linked by O-H⋯O hydrogen bonds into chains running parallel to [100]. In turn, the anionic chains are linked through the 1,2,4-triazolium cations by charge-assisted +N-H⋯O- hydrogen bonds into sheets aligned parallel to (01). The sheets are further stacked through π-π inter-actions between the 1,2,4-triazolium rings [centroid-to-centroid distance = 3.642 (3) Å, normal distance = 3.225 (3) Å, slippage 1.691 Å], resulting in the formation of a three-dimensional supra-molecular network. Hirshfeld surface analysis of the title salt suggests that the most significant contributions to the crystal packing are by H⋯O/O⋯H and H⋯N/N⋯H contacts involving the hydrogen bonds.

| S-EPMC7001815 | biostudies-literature

Ethyl 5-chloro-methyl-2-methyl-sulfanyl-7-phenyl-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidine-6-carboxyl-ate.

Project description:In the title compound, C(16)H(17)ClN(4)O(2)S, the bicyclic triazolopyrimidine ring system is nearly planar and oriented with respect to the benzene ring at a dihedral angle of 87.24?(3)°. In the crystal structure, inter-molecular N-H?N hydrogen bonds link the mol-ecules into centrosymmetric dimers; an intra-molecular C-H?O hydrogen bond is also present.

| S-EPMC2915003 | biostudies-literature

Bis(cyanato-κN)bis-(5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-κN)zinc.

Project description:In the title complex, [Zn(NCO)(2)(C(7)H(8)N(4))(2)], the Zn(II) ion exhibits a distorted tetra-hedral coordination geometry. The coordination environment is formed by two 5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine (dmtp) ligands, coordinated through the N atom in position 3, and two cyanate anions inter-acting by their N atoms. Supra-molecular dimers are generated by stacking inter-actions between the pyrimidine rings of two ligands related by an inversion center [centroid-centroid distance = 3.5444 (18) Å].

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2-Methyl-sulfanyl-1,2,4-triazolo[1,5-a]quinazolin-5(4H)-one.

Project description:The non-H atoms of the title compound, C(10)H(8)N(4)OS, lie approximately in a common plane (r.m.s. deviation = 0.058?Å). In the crystal, two mol-ecules are linked across a center of inversion by a pair of N-H?N hydrogen bonds, forming a a dimer.

| S-EPMC3379379 | biostudies-literature

2-Methyl-sulfonyl-1,2,4-triazolo[1,5-a]quinazolin-5(4H)-one.

Project description:The triazoloquinazoline fused-ring system of the title compound, C(10)H(8)N(4)O(3)S, is essentially planar (r.m.s. deviation = 0.027?Å). In the crystal, adjacent mol-ecules are linked by N-H?O(sulfon-yl) hydrogen bonds, generating a helical chain running along the b axis.

| S-EPMC3379380 | biostudies-literature

2-Methyl-sulfanyl-1,2,4-triazolo[1,5-a]quinazoline-5(4H)-thione.

Project description:In the title compound, C10H8N4S2, comprising fused six-, six- and five-membered rings, the mol-ecule is close to being planar (r.m.s. deviation of the non-H atoms = 0.041?Å). The S-bound methyl group is folded away from the single N atom of the triazole ring and the NH group of the six-membered ring, allowing for the formation of centrosymmetric eight-membered {?HNCN}2 synthons in the crystal. The resulting inversion dimers are connected into supra-molecular stacks aligned along the b-axis direction by ?-? inter-actions [centroid-centroid distances = 3.6531?(12) and 3.7182?(12)?Å].

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Ethyl 2-benzyl-sulfanyl-7-(2-chloro-phen-yl)-5-methyl-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidine-6-carboxyl-ate.

Project description:In the title compound, C(22)H(21)ClN(4)O(2)S, the bicyclic triazolopyrimidine ring system is nearly planar, and oriented at dihedral angles of 89.45?(3)° with respect to the chlorobenzene ring and 87.03?(3)° with respect to the terminal phenyl ring. In the crystal structure, mol-ecules are linked by ?-? stacking inter-actions between the triazolopyrimidine rings [centroid-centroid distances of 3.88?(1) and 3.63?(1)?Å].

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