Browse
Submit Data
Databases
API
Help

Dataset Information

5 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthesis, crystal structure and Hirshfeld surface analysis of (4-methylphenyl)[1-(pentafluorophenyl)-5-(trifluoromethyl)-1H-1,2,3-triazol-4-yl]methanone

ABSTRACT: The title compound was obtained via the reaction of 1-azido-2,3,4,5,6-pentafluorobenzene with 4,4,4-trifluoro-1-(p-tolyl)butane-1,3-dione using triethylamine as a base catalyst and solvent. In the crystal, the molecules are linked by C—H⋯F and C—H⋯O hydrogen bonds as well as by aromatic π–π stacking interactions into a three-dimensional network. The title compound, C17H7F8N3O, was obtained via the reaction of 1-azido-2,3,4,5,6-pentafluorobenzene with 4,4,4-trifluoro-1-(p-tolyl)butane-1,3-dione using triethylamine as a base catalyst and solvent. The dihedral angles between the pentafluorophenyl (A), triazole (B) and p-tolyl (C) rings are A/B = 62.3 (2), B/C = 43.9 (3) and A/C = 19.1 (3)°. In the crystal, the molecules are linked by C—H⋯F and C—H⋯O hydrogen bonds as well as by aromatic π–π stacking interactions into a three-dimensional network. To further analyse the intermolecular interactions, a Hirshfeld surface analysis was performed.

SUBMITTER: Pokhodylo N

PROVIDER: S-EPMC8587975 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

[4-(4-Meth-oxy-phen-yl)-2-(pyridin-3-yl)-1,3-thia-zol-5-yl][4-(tri-fluoro-meth-yl)phen-yl]methanone.

Project description:In the title compound, C23H15F3N2O2S, the thia-zole ring makes dihedral angles of 12.98?(13), 49.30?(11) and 49.83?(12)° with the pyridine ring, the meth-oxy-phenyl ring and the (tri-fluoro-meth-yl)phenyl ring, respectively. In the crystal, mol-ecules are connected via C-H?O hydrogen bonds, forming chains along [010]. There are also C-H?? and C-F?? inter-actions present, forming a three-dimensional structure.

| S-EPMC3884424 | biostudies-literature

Crystal structure of (4-hy-droxy-piperidin-1-yl)[4-(tri-fluoro-meth-yl)phen-yl]methanone.

Project description:The title compound, C13H14NO2F3, crystallises with two mol-ecules, A and B, in the asymmetric unit, with similar conformations. The dihedral angles between the piperidine and phenyl rings are 83.76 (2) and 75.23 (2)° in mol-ecules A and B, respectively. The bond-angle sums around the N atoms [359.1 and 359.7° for mol-ecules A and B, respectively] indicate sp (2) hybridization for these atoms. In the crystal, O-H⋯O hydrogen bonds link the mol-ecules into separate [100] chains of A and B mol-ecules. The chains are cross-linked by C-H⋯O inter-actions, generating alternating (001) sheets of A and B mol-ecules.

| S-EPMC4647357 | biostudies-literature

Crystal structure analysis of [5-(4-meth-oxy-phen-yl)-2-methyl-2H-1,2,3-triazol-4-yl](thio-phen-2-yl)methanone.

Project description:The title compound, C15H13N3O2S, crystallizes in the monoclinic space group P21/n and its mol-ecular conformation is stabilized via intra-molecular C-H?O and C-H?N contacts. The supra-molecular structure is mainly governed by C-H?N hydrogen-bonded centrosymmetric dimers, C-H?O and C-H?S hydrogen bonds and S?? and ?-? stacking inter-actions which, together, lead to the formation of a layered crystal packing. The inter-molecular inter-actions were further evaluated through the mol-ecular electrostatic potential map and Hirshfeld fingerprint analysis.

| S-EPMC6073004 | biostudies-literature

Crystal structures of 3-fluoro-N-[2-(tri-fluoro-meth-yl)phen-yl]benzamide, 3-bromo-N-[2-(tri-fluoro-meth-yl)phen-yl]benzamide and 3-iodo-N-[2-(tri-fluoro-meth-yl)phen-yl]benzamide.

Project description:In the title compounds, C14H9F4NO, (I), C14H9BrF3NO, (II), and C14H9F3INO, (III), the two benzene rings are inclined to one another by 43.94 (8)° in mol-ecule A and 55.66 (7)° in mol-ecule B of compound (I), which crystallizes with two independent mol-ecules in the asymmetric unit, but by only 10.40 (12)° in compound (II) and 12.5 (2)° in compound (III). In the crystals of all three compounds, N-H⋯O hydrogen bonds link the mol-ecules to form chains propagating along the a-axis direction for (I), and along the b-axis direction for (II) and (III). In the crystal of (I), -A-B-A-B- chains are linked by C-H⋯O hydrogen bonds, forming layers parallel to (010). Within the layers there are weak offset π-π inter-actions present [inter-centroid distances = 3.868 (1) and 3.855 (1) Å]. In the crystals of (II) and (III), the chains are linked via short halogen-halogen contacts [Br⋯Br = 3.6141 (4) Å in (II) and I⋯I = 3.7797 (5) Å in (III)], resulting in the formation of ribbons propagating along the b-axis direction.

| S-EPMC4908555 | biostudies-literature

<i>N</i>-[2-(Tri-fluoro-meth-yl)phen-yl]maleamic acid: crystal structure and Hirshfeld surface analysis.

Project description:The title mol-ecule, C11H8F3NO3, adopts a cis configuration across the -C=C- double bond in the side chain and the dihedral angle between the phenyl ring and side chain is 47.35 (1)°. The -COOH group adopts a syn conformation (O=C-O-H = 0°), unlike the anti conformation observed in related maleamic acids. In the crystal, inversion dimers linked by pairs of O-H⋯O hydrogen bonds are connected via N-H⋯O hydrogen bonds and C-H⋯O inter-actions into (100) sheets, which are cross-linked by another C-H⋯O inter-action to result in a three-dimensional network. The Hirshfeld surface fingerprint plots show that the highest contribution to surface contacts arises from O⋯H/H⋯O contacts (26.5%) followed by H⋯F/F⋯H (23.4%) and H⋯H (17.3%).

| S-EPMC6658960 | biostudies-literature

2-[4-(Tri-fluoro-meth-yl)phen-yl]-1H-benzimidazole.

Project description:In the title compound, C14H9F3N2, the mean planes of the benzimidazole ring system and the tri-fluoro-methyl-substituted benzene ring form a dihedral angle of 30.1?(1)°. In the crystal, mol-ecules are linked by N-H?N hydrogen bonds into chains along [010]. Weak C-H?F hydrogen bonds and a weak C-H?? inter-action connect the chains into a two-dimensional network parallel to (001).

| S-EPMC4120605 | biostudies-literature

Crystal structure, Hirshfeld surface analysis and DFT studies of 4-methyl-2-({[4-(tri-fluoro-meth-yl)phen-yl]imino}-meth-yl)phenol.

Project description:The title compound, C15H12F3NO, crystallizes with one mol-ecule in the asymmetric unit. The configuration of the C=N bond is E and there is an intra-molecular O-H⋯N hydrogen bond present, forming an S(6) ring motif. The dihedral angle between the mean planes of the phenol and the 4-tri-fluoro-methyl-phenyl rings is 44.77 (3)°. In the crystal, mol-ecules are linked by C-H⋯O inter-actions, forming polymeric chains extending along the a-axis direction. The Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from C⋯H/H⋯C (29.2%), H⋯H (28.6%), F⋯H/H⋯F (25.6%), O⋯H/H⋯O (5.7%) and F⋯F (4.6%) inter-actions. The density functional theory (DFT) optimized structure at the B3LYP/6-311 G(d,p) level is compared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap. The crystal studied was refined as an inversion twin.

| S-EPMC7405564 | biostudies-literature

{5-Methyl-1-[8-(trifluoro-meth-yl)quinolin-4-yl]-1H-1,2,3-triazol-4-yl}(morpholino)methanone.

Project description:In the title mol-ecule, C(18)H(16)F(3)N(5)O(2), the dihedral angle between the pyridine ring and the fused benzene ring is 4.50 (10)°. The triazole ring makes dihedral angles of 54.48 (12) and 57.91 (11)° with the pyridine and benzene rings, respectively. The morpholine ring atoms are disordered over two positions; the site-occupancy factors are ca 0.53 and 0.47. Inter-molecular C-H⋯F hydrogen bonding is found in the crystal structure. Furthermore, C-H⋯O and C-H⋯N intra-molecular contacts are also present.

| S-EPMC2959961 | biostudies-literature

1-(4-Meth-oxy-phen-yl)-2-[4-(tri-fluoro-meth-yl)phen-yl]-1H-phenanthro[9,10-d]imidazole.

Project description:In the title compound, C29H19F3N2O, a phenanthroline-fused imidazole tetra-cyclic system, the fused benzene rings deviate slightly from the central ring and make dihedral angles with this ring of 3.47 (8) and 3.05 (8)°. The tri-fluoro-methyl-phenyl ring is roughly coplanar with the phenanthroline-fused imidazole tetra-cyclic system [dihedral angle = 11.02 (6)°], while the meth-oxy-phenyl ring is almost perpendicular [dihedral angle = 87.65 (6)°]. There are intra-molecular C-H ⋯π inter-actions involving the meth-oxy-phenyl ring and the central phenanthroline ring, as well as an inter-molecular C-H⋯π inter-action involving the phenanthroline ring. In addition, there is an inter-molecular π-π inter-action involving the central phenanthroline ring and the tri-fluoro-methyl-phenyl ring [centroid-centroid distance = 3.685 (2) Å], as well as C-H⋯N inter-actions linking the mol-ecules into dimers.

| S-EPMC3793785 | biostudies-literature

{2-[(1,3-Benzo-thia-zol-2-yl)meth-oxy]-5-fluoro-phen-yl}(4-chloro-phen-yl)methanone.

Project description:The asymmetric unit of the title compound, C21H13ClFNO2S, contains two independent mol-ecules with similar conformations. In the mol-ecules, the thia-zole ring is essentially planar [maximum atomic deviations = 0.014 (4) and 0.023 (5) Å] and is oriented with respect to the fluoro-phenyl ring and chloro-phenyl rings at 9.96 (18) and 70.39 (18)° in one mol-ecule and at 7.50 (18) and 68.43 (18)° in the other; the dihedral angles between the fluoro-phenyl and chloro-phenyl rings are 64.9 (2) and 64.6 (2)°, respectively. Inter-molecular C-H⋯O and C-H⋯F hydrogen bonds stabilize the three-dimensional supra-molecular architecture. Weak C-H⋯π and π-π inter-actions [centroid-centroid distance = 3.877 (3) Å] lead to a criss-cross mol-ecular packing along the c axis.

| S-EPMC3772451 | biostudies-literature