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 N-(5-iodo-4-phenyl-thia-zol-2-yl)acetamide.

ABSTRACT: Two crystallographically independent mol-ecules (A and B) are present in the asymmetric unit of the title compound, C₁₁H₉IN₂OS, which differ mainly in the dihedral angle between the phenyl and thia-zole rings [38.94 (16) and 32.12 (15)°, respectively]. In the crystal, the mol-ecules form ⋯A⋯B⋯A⋯B⋯ chains along the [001] and [010] directions through moderate N-H⋯O hydrogen bonds and C-H⋯π inter-actions, respectively. The overall three-dimensional network is formed by I⋯I and I⋯S inter-actions. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯C/C⋯H (26.2%), H⋯H (20.9%), H⋯I/I⋯H (19.4%) and H⋯O/O⋯H (6.8%) inter-actions.

SUBMITTER: Herrera-Espana AD

PROVIDER: S-EPMC6658950 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Crystal structure and Hirshfeld surface analysis of N-(5-iodo-4-phenyl-thia-zol-2-yl)acetamide.

Herrera-España Angel D AD Aguilera-González Jesús J Mena-Rejón Gonzalo J GJ Hernández-Ortega Simón S Cáceres-Castillo David D

Acta crystallographica. Section E, Crystallographic communications 20190503 Pt 6

Two crystallographically independent mol-ecules (A and B) are present in the asymmetric unit of the title compound, C11H9IN2OS, which differ mainly in the dihedral angle between the phenyl and thia-zole rings [38.94 (16) and 32.12 (15)°, respectively]. In the crystal, the mol-ecules form ⋯A⋯B⋯A⋯B⋯ chains along the [001] and [010] directions through moderate N-H⋯O hydrogen bonds and C-H⋯π inter-actions, respectively. The o ...[more]

PMID: 31391952

Similar Datasets

N-(Thia-zol-2-yl)acetamide.

Project description:The title compound, C(5)H(6)N(2)OS, was synthesized from acetyl chloride and 2-amino-thia-zole in dry acetone. The asymmetric unit contains two mol-ecules. The crystal structure is stabilized by N-H⋯N and C-H⋯O hydrogen bonds.

| S-EPMC2962142 | biostudies-literature

N'-(1,3-Benzo-thia-zol-2-yl)benzene-sulfono-hydrazide: crystal structure, Hirshfeld surface analysis and computational chemistry.

Project description:The asymmetric unit of the title compound, C13H11N3O2S2, comprises two independent mol-ecules (A and B); the crystal structure was determined by employing synchrotron radiation. The mol-ecules exhibit essentially the same features with an almost planar benzo-thia-zole ring (r.m.s. deviation = 0.026 and 0.009 Å for A and B, respectively), which forms an inclined dihedral angle with the phenyl ring [28.3 (3) and 29.1 (3)°, respectively]. A difference between the mol-ecules is noted in a twist about the N-S bonds [the C-S-N-N torsion angles = -56.2 (5) and -68.8 (5)°, respectively], which leads to a minor difference in orientation of the phenyl rings. In the mol-ecular packing, A and B are linked into a supra-molecular dimer via pairwise hydrazinyl-N-H⋯N(thiazol-yl) hydrogen bonds. Hydrazinyl-N-H⋯O(sulfon-yl) hydrogen bonds between A mol-ecules assemble the dimers into chains along the a-axis direction, while links between centrosymmetrically related B mol-ecules, leading to eight-membered {⋯HNSO}2 synthons, link the mol-ecules along [001]. The result is an undulating supra-molecular layer. Layers stack along the b-axis direction with benzo-thia-zole-C-H⋯O(sulfon-yl) points of contact being evident. The analyses of the calculated Hirshfeld surfaces confirm the relevance of the above inter-molecular inter-actions, but also serve to further differentiate the weaker inter-molecular inter-actions formed by the independent mol-ecules, such as π-π inter-actions. This is also highlighted in distinctive energy frameworks calculated for the individual mol-ecules.

| S-EPMC6509675 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of 1-(2-amino-4-methyl-1,3-thia-zol-5-yl)ethan-1-one.

Project description:In the title compound, C6H8N2OS, all atoms except for the methyl H atoms are coplanar, with a maximum deviation of 0.026 (4) Å. In the crystal, pairs of mol-ecules are linked by N-H⋯N hydrogen bonds, forming R 2 2(8) ring motifs. Dimers are connected by N-H⋯O hydrogen bonds, forming layers parallel to the (102) plane. Consolidating the mol-ecular packing, these layers are connected by C-H⋯π inter-actions between the center of the 1,3-thia-zole ring and the H atom of the methyl group attached to it, as well as C=O⋯π inter-actions between the center of the 1,3-thia-zole ring and the O atom of the carboxyl group. According to a Hirshfeld surface study, H⋯H (37.6%), O⋯H/H⋯O (16.8%), S⋯H/H⋯S (15.4%), N⋯H/H⋯N (13.0%) and C⋯H/H⋯C (7.6%) inter-actions are the most significant contributors to the crystal packing.

| S-EPMC10561208 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of (Z)-4-{[4-(3-methyl-3-phenyl-cyclo-but-yl)thia-zol-2-yl]amino}-4-oxobut-2-enoic acid.

Project description:The title cyclo-butyl compound, C18H18N2O3S, was synthesized by the inter-action of 4-(3-methyl-3-phenyl-cyclo-but-yl)thia-zol-2-amine and maleic anhydride, and crystallizes in the ortho-rhom-bic space group P212121 with Z' = 1. The mol-ecular geometry is partially stabilized by an intra-molecular N-H⋯O hydrogen bond forming an S 1 1(7) ring motif. The mol-ecule is non-planar with a dihedral angle of 88.29 (11)° between the thia-zole and benzene rings. In the crystal, the mol-ecules are linked by O-H⋯N hydrogen bonds, forming supra-molecular ribbons with C 1 1(9) chain motifs. To further analyze the inter-molecular inter-actions, a Hirshfeld surface analysis was performed. The results indicate that the most important contributions to the overall surface are from H⋯H (43%), C⋯H (18%), O⋯H (17%) and N⋯H (6%), inter-actions.

| S-EPMC8819446 | biostudies-literature

N-(1,3-Benzo-thia-zol-2-yl)acetamide.

Project description:The title compound, C9H8N2OS, crystallizes with two mol-ecules (A and B) in the asymmetric unit. The dihedral angles between the mean planes of the 1,3-benzo-thia-zol-2-yl ring system and the acetamide group are 2.7 (4) (mol-ecule A) and 7.2 (2) Å (mol-ecule B). In the crystal, pairs of N-H⋯N hydrogen bonds link the A and B mol-ecules into dimers, generating R 2 (2)(8) loops. The dimers stack along [100].

| S-EPMC3884296 | biostudies-literature

The crystal structures of two isomers of 5-(phenyl-iso-thia-zol-yl)-1,3,4-oxa-thia-zol-2-one.

Project description:The syntheses and crystal structures of two isomers of phenyl iso-thia-zolyl oxa-thia-zolone, C11H6N2O2S2, are described [systematic names: 5-(3-phenyl-iso-thia-zol-5-yl)-1,3,4-oxa-thia-zol-2-one, (I), and 5-(3-phenyl-iso-thia-zol-4-yl)-1,3,4-oxa-thia-zol-2-one, (II)]. There are two almost planar (r.m.s. deviations = 0.032 and 0.063 Å) mol-ecules of isomer (I) in the asymmetric unit, which form centrosymmetric tetra-mers linked by strong S⋯N [3.072 (2) Å] and S⋯O contacts [3.089 (1) Å]. The tetra-mers are π-stacked parallel to the a-axis direction. The single mol-ecule in the asymmetric unit of isomer (II) is twisted into a non-planar conformation by steric repulsion [dihedral angles between the central iso-thia-zolyl ring and the pendant oxa-thia-zolone and phenyl rings are 13.27 (6) and 61.18 (7)°, respectively], which disrupts the π-conjugation between the heteroaromatic iso-thia-zoloyl ring and the non-aromatic oxa-thia-zolone heterocycle. In the crystal of isomer (II), the strong S⋯O [3.020 (1) Å] and S⋯C contacts [3.299 (2) Å] and the non-planar structure of the mol-ecule lead to a form of π-stacking not observed in isomer (I) or other oxa-thia-zolone derivatives.

| S-EPMC5683500 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of 2-(4-chloro-phen-yl)-4-(di-meth-oxy-meth-yl)-5-phenyl-1,3-thia-zole.

Project description:In the title compound, C18H16ClNO2S, the thia-zole ring subtends dihedral angles of 13.12 (14) and 43.79 (14) ° with the attached chloro-phenyl and phenyl rings, respectively. In the crystal, C-H⋯π inter-actions link the mol-ecules, forming a three-dimensional network. The roles of the various inter-molecular inter-actions were clarified by Hirshfeld surface analysis, which reveals that the most important contributions to the crystal packing are from H⋯H (39.2%), H⋯C/C⋯H (25.2%), Cl⋯H/H⋯Cl (11.4%) and O⋯H/H⋯O (8.0%) contacts.

| S-EPMC9431783 | biostudies-literature

2,2-Diphenyl-N-(1,3-thia-zol-2-yl)acetamide.

Project description:In the title mol-ecule, C(17)H(14)N(2)OS, the mean plane of the acetamide group forms dihedral angles of 75.79 (5), 81.85 (6) and 12.32 (5)° with the two phenyl rings and the thia-zole ring, respectively. In the crystal, N-H⋯N hydrogen bonds link pairs of mol-ecules into inversion dimers with R(2) (2)(8) ring motifs. The crystal packing is further stabilized by C-H⋯π inter-actions and by π-π inter-actions with a centroid-centroid distance of 3.6977 (5) Å.

| S-EPMC3344455 | biostudies-literature

2-(Naphthalen-1-yl)-N-(1,3-thia-zol-2-yl)acetamide.

Project description:In the title compound, C(15)H(12)N(2)OS, the naphthalene ring system [maximum deviation = 0.026 (1) Å] forms a dihedral angle of 85.69 (6)° with the thia-zole ring [maximum deviation = 0.010 (1) Å]. In the crystal, inversion dimers linked by pairs of N-H⋯N hydrogen bonds generate R(2) (2)(8) loops. The dimers are linked by C-H⋯O hydrogen bonds into chains propagating along [110].

| S-EPMC3414920 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of 2-{[(4-iodo-phen-yl)imino]-meth-yl}-4-nitro-phenol.

Project description:The title compound, C13H9IN2O3, was synthesized by a condensation reaction between 2-hy-droxy-5-nitro-benzaldehyde and 4-iodo-aniline, and crystallizes in the ortho-rhom-bic space group Pna21. The 4-iodo-benzene ring is inclined to the phenol ring by a dihedral angle of 39.1 (2)°. The configuration about the C=N double bond is E. The crystal structure features C-H⋯O hydrogen-bonding inter-actions. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the packing arrangement are O⋯H/H⋯O (26.9%) and H⋯H (22.0%) inter-actions.

| S-EPMC7336806 | biostudies-literature