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Crystal structure, Hirshfeld surface analysis and DFT study of N-(2-amino-5-methyl-phen-yl)-2-(5-methyl-1H-pyrazol-3-yl)acetamide.

ABSTRACT: The title mol-ecule, C₁₃H₁₆N₄O, adopts an angular conformation. In the crystal a layer structure is generated by N-H⋯O and N-H⋯N hydrogen bonds together with C-H⋯π(ring) inter-actions. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (53.8%), H⋯C/C⋯H (21.7%), H⋯N/N⋯H (13.6%), and H⋯O/O⋯H (10.8%) inter-actions. The optimized structure calculated using density functional theory (DFT) at the B3LYP/ 6-311 G(d,p) level is compared with the experimentally determined structure in the solid state. The calculated HOMO-LUMO energy gap is 5.0452 eV.

SUBMITTER: Al Ati G

PROVIDER: S-EPMC8183437 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Crystal structure and Hirshfeld surface analysis of N-{2-[(E)-(4-methyl-benzyl-idene)amino]-phen-yl}-2-(5-methyl-1-H-pyrazol-3-yl)acetamide hemihydrate.

Project description:The asymmetric unit of the title compound, C20H20N4O·0.5H2O, contains two independent organic mol-ecules (1 and 2) and a water mol-ecule of crystallization. The two mol-ecules differ primarily in the dihedral angles between the aromatic rings, which are 7.79?(7) and 29.89?(7)° in mol-ecules 1 and 2, respectively. In each mol-ecule there is intra-molecular C-H?O hydrogen bond forming an S(6) ring motif. In mol-ecule 1 there is an intra-molecular N-H??(pyrazole) inter-action and an intra-molecular C-H??(pyrazole) inter-action present. Mol-ecule 1 is linked to mol-ecule 2 by a C-H??(benzene ring) inter-action. An intra-molecular N-H?N hydrogen bond and an intra-molecular C-H?N hydrogen bond are also present in mol-ecule 2. In the crystal, the three components are linked by Owater-H?N, N-H?Owater and N-H?N hydrogen bonds, forming chains along the [100] direction. The chains are linked by C-H?O and C-H?N hydrogen bonds, forming layers parallel to the ab plane. Finally, the layers are linked by C-H?? inter-actions, forming a three-dimensional structure.

| S-EPMC6362653 | biostudies-literature

Crystal structure, Hirshfeld surface analysis and computational study of 2-chloro-N-[4-(methyl-sulfan-yl)phen-yl]acetamide.

Project description:In the title compound, C9H10ClNOS, the amide functional group -C(=O)NH- adopts a trans conformation with the four atoms nearly coplanar. This conformation promotes the formation of a C(4) hydrogen-bonded chain propagating along the [010] direction. The central part of the mol-ecule, including the six-membered ring, the S and N atoms, is fairly planar (r.m.s. deviation of 0.014). The terminal methyl group and the C(=O)CH2 group are slightly deviating out-of-plane while the terminal Cl atom is almost in-plane. Hirshfeld surface analysis of the title compound suggests that the most significant contacts in the crystal are H⋯H, H⋯Cl/Cl⋯H, H⋯C/C⋯H, H⋯O/O⋯H and H⋯S/S⋯H. π-π inter-actions between inversion-related mol-ecules also contribute to the crystal packing. DFT calculations have been performed to optimize the structure of the title compound using the CAM-B3LYP functional and the 6-311 G(d,p) basis set. The theoretical absorption spectrum of the title compound was calculated using the TD-DFT method. The analysis of frontier orbitals revealed that the π-π* electronic transition was the major contributor to the absorption peak in the electronic spectrum.

| S-EPMC7133040 | 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, DFT calculations and Hirshfeld surface analysis of 3-(4-methyl-phen-yl)-6-nitro-1H-indazole.

Project description:The asymmetric unit of the title compound, C14H11N3O3, consists of two independent mol-ecules having very similar conformations in which the indazole moieties are planar. The independent mol-ecules are distinguished by small differences in the rotational orientations of the nitro groups. In the crystal, N-H?O and C-H?O hydrogen bonds form zigzag chains along the b-axis direction. Additional C-H?O hydrogen bonds link the chains into layers parallel to (10). These are connected by slipped ?-stacking and C-H??(ring) inter-actions.

| S-EPMC6281119 | biostudies-literature

Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-2-{[(3-chloro-4-methyl-phen-yl)imino]-meth-yl}-4-methyl-phenol.

Project description:The title compound, C15H14ClNO, was synthesized by condensation reaction of 2-hy-droxy-5-methyl-benzaldehyde and 3-chloro-4-methyl-aniline, and crystallizes in the monoclinic space group P21/c. The 3-chloro-benzene ring is inclined to the phenol ring by 9.38?(11)°. The configuration about the C=N bond is E and an intra-molecular O-H?N hydrogen bond forms an S(6) ring motif. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the packing arrangement are from H?H (43.8%) and C?H/H?C (26.7%) 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.

| S-EPMC7405573 | biostudies-literature

Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-4-methyl-2-{[(2-methyl-3-nitro-phen-yl)imino]-meth-yl}phenol.

Project description:The title compound, C15H14N2O3, was prepared by condensation of 2-hy-droxy-5-methyl-benzaldehyde and 2-methyl-3-nitro-phenyl-amine in ethanol. The configuration of the C=N bond is E. An intra-molecular O-H?N hydrogen bond is present, forming an S(6) ring motif and inducing the phenol ring and the Schiff base to be nearly coplanar [C-C-N-C torsion angle of 178.53?(13)°]. In the crystal, mol-ecules are linked by C-H?O inter-actions, forming chains along the b-axis direction. The Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H?H (37.2%), C?H (30.7%) and O?H (24.9%) inter-actions. The gas phase density functional theory (DFT) optimized structure at the B3LYP/ 6-311?G(d,p) level is compared to the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.

| S-EPMC7534237 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of N-[(2-hy-droxy-naphthalen-1-yl)(3-methyl-phen-yl)meth-yl]acetamide.

Project description:The title compound, C20H19NO2, is of inter-est as a precursor to biologically active substituted quinolines and related compounds. This compound crystallizes with two independent mol-ecules (A and B) in the asymmetric unit. The dihedral angles between mean planes of the methyl-phenyl ring and the naphthalene ring system are 78.32?(6) and 84.70?(6)° in mol-ecules A and B, respectively. In the crystal, the anti-ferroelectric packing of mol-ecules A and B is of an ABBAABB type along the b-axis direction. The crystal structure features N-H?O, O-H?O and weak C-H?O hydrogen bonds, which link the mol-ecules into infinite chains propagating along the b-axis direction.

| S-EPMC6038626 | 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

Crystal structure, Hirshfeld surface analysis and DFT study of 6-bromo-3-(5-bromo-hex-yl)-2-[4-(di-methyl-amino)-phen-yl]-3H-imidazo[4,5-b]pyridine.

Project description:In the title mol-ecule, C20H24Br2N4, the imidazo-pyridine moiety is not planar as indicated by the dihedral angle of 2.0?(2)° between the constituent rings; the 4-di-methyl-amino-phenyl ring is inclined to the mean plane of the imidazole ring by 27.4?(1)°. In the crystal, two sets of C-H??(ring) inter-actions form stacks of mol-ecules extending parallel to the a-axis direction. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H?H (42.2%), H?C/C?H (23.1%) and H?Br/Br?H (22.3%) inter-actions. The optimized structure calculated using density functional theory (DFT) at the B3LYP/ 6-311?G(d,p) level is compared with the experimentally determined structure in the solid state. The calculated HOMO-LUMO energy gap is 2.3591?eV.

| S-EPMC7405593 | biostudies-literature

Hirshfeld surface analysis and crystal structure of N-(2-meth-oxy-phen-yl)acetamide.

Project description:The title compound, C9H11NO2, was obtained as unexpected product from the reaction of (4-{2-benz-yloxy-5-[(E)-(3-chloro-4-methyl-phen-yl)diazen-yl]benzyl-idene}-2-phenyl-oxazol-5(4H)-one) with 2-meth-oxy-aniline in the presence of acetic acid as solvent. The amide group is not coplanar with the benzene ring, as shown by the C-N-C-O and C-N-C-C torsion angles of -2.5 (3) and 176.54 (19)°, respectively. Hirshfeld surface analysis and two-dimensional fingerprint plots indicate that the most important contributions to the crystal packing are from H⋯H (53.9%), C⋯H/H⋯C (21.4%), O⋯H/H⋯O (21.4%) and N⋯H/H⋯N (1.7%) inter-actions.

| S-EPMC6658953 | biostudies-literature

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