Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

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

ABSTRACT: The title compound, C₁₆H₁₇NO, is a Schiff base that exists in the enol-imine tautomeric form and adopts a Z configuration. The mol-ecule is non-planar, with the twisted rings making a dihedral angle of 39.92 (4)°. The intra-molecular O-H⋯N hydrogen bond forms an S(6) ring motif. In the crystal, mol-ecules are linked by C-H⋯π inter-actions and very weak π-π stacking inter-actions also help to consolidate the crystal packing. A Hirshfeld surface analysis was performed to investigate the contributions of different inter-molecular contacts within the supra-molecular structure. The major contributions are from H⋯H (65%), C⋯H (19.2%) and O⋯H (6.6%) inter-actions.

SUBMITTER: Kansiz S

PROVIDER: S-EPMC8587990 | biostudies-literature | 2021 Nov

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

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

Kansiz Sevgi S Gul Adem A Dege Necmi N Agar Erbil E Saif Eiad E

Acta crystallographica. Section E, Crystallographic communications 20211013 Pt 11

The title compound, C16H17NO, is a Schiff base that exists in the enol-imine tautomeric form and adopts a Z configuration. The mol-ecule is non-planar, with the twisted rings making a dihedral angle of 39.92 (4)°. The intra-molecular O-H⋯N hydrogen bond forms an S(6) ring motif. In the crystal, mol-ecules are linked by C-H⋯π inter-actions and very weak π-π stacking inter-actions also help to consolidate the crystal packing. A Hirshfeld surface analysis was per ...[more]

PMID: 34868641

Similar Datasets

2,4-Di-bromo-6-{[(5-chloro-2-methyl-phen-yl)imino]-meth-yl}phenol.

Project description:In the mol-ecular structure of the title Schiff base, C14H10Br2ClNO, the chloro-phenyl ring and di-bromo-phenol ring are almost coplanar; the dihedral angle between the planes of the two rings is 10.50 (18)°. There is an intra-molecular O-H⋯N hydrogen bond, with an O⋯N distance of 2.576 (4)Å. The crystal structure is stabilized by π-π stacking of neighbouring aromatic rings along the b-axis direction [centroid-centroid distance = 3.6896 (5) Å].

| S-EPMC3770443 | biostudies-literature

2-[(2,4-Dimethyl-phen-yl)imino-meth-yl]-6-methyl-phenol.

Project description:The title compound, C(16)H(17)NO, is a Schiff base which adopts the phenol-imine tautomeric form in the solid state. The mol-ecule is almost planar, with a dihedral angle of 4.61 (4)° between the aromatic rings. The molecular structure is stabilized by an intramolecular O-H⋯N hydrogen bond which generates a six membered ring.

| S-EPMC2969980 | biostudies-literature

Crystal structure of 4-chloro-2-{(E)-[(3,4-di-methyl-phen-yl)imino]-meth-yl}phenol.

Project description:In the title compound, C15H14ClNO, which is isostructural with its bromo analogue [Tahir et al. (2012 ▶). Acta Cryst., E68, o2730], the dihedral angle between the planes of the aromatic rings is 2.71 (7)° and an intra-molecular O-H⋯N hydrogen bond closes an S(6) ring. In the crystal, extremely weak C-H⋯π inter-actions link the mol-ecules into a three-dimensional network.

| S-EPMC4459303 | biostudies-literature

Crystal structure of (E)-5-di-ethyl-amino-2-({[4-(di-methyl-amino)-phen-yl]imino}-meth-yl)phenol.

Project description:The title Schiff base compound, C19H25N3O, is approximately planar, with a dihedral angle of 9.03 (13)° between the planes of the aromatic rings, and has an E conformation about the N=C bond. The mol-ecular structure is stabilized by an intra-molecular O-H⋯N hydrogen bond, with an S(6) ring motif. In the crystal, mol-ecules are linked by C-H⋯π inter-actions, forming sheets parallel to the bc plane.

| S-EPMC4518928 | biostudies-literature

2-[(E)-(2,4-Dimethyl-phen-yl)imino-meth-yl]phenol.

Project description:The asymmetric unit of the title compound, C(15)H(15)NO, contains two independent mol-ecules, both of which exist in trans configurations with respect to the C=N bonds [1.278?(2) and 1.279?(2)?Å]. In each mol-ecule, intra-molecular O-H?N hydrogen bonds generate S(6) ring motifs. In one mol-ecule, the benzene rings form a dihedral angle of 13.38?(9)°, while in the other mol-ecule the dihedral angle is 30.60?(10)°. In the crystal, the two independent mol-ecules are linked via weak inter-molecular C-H?O hydrogen bonds.

| S-EPMC3212320 | 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

2-[(2,4-Dimethyl-phen-yl)imino-meth-yl]-3,5-dimethoxy-phenol.

Project description:X-ray analysis reveals that the title Schiff base compound, C(17)H(19)NO(3), possesses both OH and NH tautomeric character in its mol-ecular structure. The occupancies of the enol and keto tautomers are 0.62?(3) and 0.38?(3), respectively. The presence of the minor keto form could not be confirmed from the IR spectrum. The mol-ecule is approximately planar, the dihedral angle between the planes of the two aromatic rings being 6.97?(8)°. The mol-ecular structure of the major component is stabilized by an intra-molecular O-H?N hydrogen bond, which generates an S(6) ring motif (N-H?O hydrogen bond in the minor component).

| S-EPMC2969358 | biostudies-literature

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

Project description:In the title compound, C15H15NO, the configuration of the C=N bond of the Schiff base is E, and an intra-molecular O-H⋯N hydrogen bond is observed, forming an intra-molecular S(6) ring motif. The phenol ring is inclined by 45.73 (2)° from the plane of the aniline ring. In the crystal, mol-ecules are linked along the b axis by O-H⋯N and C-H⋯O hydrogen bonds, forming polymeric chains. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the packing arrangement are from H⋯H (56.9%) and H⋯C/C⋯H (31.2%) 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, and the HOMO-LUMO energy gap is provided. The crystal studied was refined as an inversion twin.

| S-EPMC7336782 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of (E)-2-{[(2-iodo-phen-yl)imino]-meth-yl}-6-methyl-phenol.

Project description:The title compound, C14H12INO, was synthesized by condensation of 2-hy-droxy-3-methyl-benzaldehyde and 2-iodo-aniline, and crystallizes in the ortho-rhom-bic space group P212121. The 2-iodo-phenyl and benzene rings are twisted with respect to each other, making a dihedral angle of 31.38 (2)°. The mol-ecular structure is stabilized by an O-H⋯N hydrogen bond, forming an S(6) ring motif. In the crystal, mol-ecules are linked by C-H⋯π inter-actions, resulting in the formation of sheets along the a-axis direction. Within the sheets, very weak π-π stacking inter-actions lead to additional stabilization. The Hirshfeld surface analysis and fingerprint plots reveal that the crystal structure is dominated by H⋯H (37.1%) and C⋯H (30.1%) contacts. Hydrogen bonding and van der Waals inter-actions are the dominant inter-actions in the crystal packing. The crystal studied was refined as a two-component inversion twin.

| S-EPMC7534256 | biostudies-literature

4-[(E)-(4-Methyl-phen-yl)imino-meth-yl]phenol.

Project description:In the title compound, C(14)H(13)NO, the two rings show significant deviation from coplanarity, with a dihedral angle between the two planes of 49.40 (5)°. The hy-droxy group is involved in an inter-molecular O-H⋯N hydrogen bond, forming an extended one-dimensional zigzag chain along (001).

| S-EPMC3297943 | biostudies-literature