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 1-benzyl-3-(prop-2-yn-1-yl)-2,3-dihydro-1H-1,3-benzodiazol-2-one.

ABSTRACT: The title compound, C17H14N2O, is built up from the planar benzodiazole unit linked to the benzyl and propynyl substituents. The substituents are rotated significantly out of the benzodiazole plane, where the benzyl group is inclined by 68.91?(7)° to the benzodiazole unit. In the crystal, the molecules are linked via intermolecular C—HBnzdzl?O and C—HBnzy?O (Bnzdzl = benzodiazole and Bnzy = benzyl) hydrogen bonds, enclosing R 4 4(27) ring motifs, into a network consisting of rectangular layers parallel to the bc plane which are also stacked along the a-axis direction being associated through C—H?? (ring) interactions. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H?H (43.6%), H?C/C?H (42.0%) and H?O/O?H (8.9%) interactions.

SUBMITTER: Saber A

PROVIDER: S-EPMC6281085 | biostudies-other | 2018 Dec

REPOSITORIES: biostudies-other

ACCESS DATA

Json Xml

Similar Datasets

1,3-Bis(prop-2-yn-yl)-1H-1,3-benzimid-azol-2(3H)-one.

Project description:In the title compound, C(13)H(10)N(2)O, the fused-ring system is essentially planar, the largest deviation from the mean plane being 0.015?(1)?Å. The two propynyl groups are nearly perpendicular to the benzimidazole plane, making dihedral angles of 85?(3) and 80?(2)?°, and point in opposite directions. There are two short inter-molecular C-H?O contacts to the carbonyl O atom, one involving the acetyl-enic H atom and the other a H atom of the methyl-ene group.

| S-EPMC3089259 | biostudies-literature

Crystal structure, Hirshfeld surface analysis and DFT studies of 1-benzyl-3-[(1-benzyl-1H-1,2,3-triazol-5-yl)meth-yl]-2,3-di-hydro-1H-1,3-benzo-diazol-2-one monohydrate.

Project description:In the title mol-ecule, C24H21N5O·H2O, the di-hydro-benzo-diazole moiety is not quite planar, while the whole mol-ecule adopts a U-shaped conformation in which there is a close approach of the two benzyl groups. In the crystal, chains of alternating mol-ecules and lattice water extending along [201] are formed by O-HUncoordW?ODhyr and O-HUncoordW?NTrz (UncoordW = uncoordinated water, Dhyr = di-hydro and Trz = triazole) hydrogen bonds. The chains are connected into layers parallel to (010) by C-HTrz?OUncoordW hydrogen bonds with the di-hydro-benzo-diazole units in adjacent layers inter-calating to form head-to-tail ?-stacking [centroid-to-centroid distance = 3.5694?(11)?Å] inter-actions between them, which generates the overall three-dimensional structure. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from H?H (52.1%), H?C/C?H (23.8%) and O?H/H?O (11.2%) inter-actions. Hydrogen-bonding and van der Waals inter-actions are the dominant inter-actions in the crystal packing. Density functional theory (DFT) optimized structures at the B3LYP/ 6-311?G(d,p) level are compared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.

| S-EPMC6944078 | biostudies-literature

5-Nitro-1,3-bis-(prop-2-yn-yl)-1H-1,3-benzimidazol-2(3H)-one.

Project description:The title compound, C13H9N3O3, crystallizes with two identical but differently oriented mol-ecules in the asymmetric unit, the dihedral angle between the fused-ring systems of the two molecules being 64.39 (7)°. The two prop-2-ynyl chains are located on opposite sides of the mol-ecule and are nearly perpendicular to the fused ring plane, as indicated by the C-N-C-C torsion angles in the range 106.0 (3)-113.4 (3)°. In the crystal, the two mol-ecules are linked through C-H⋯O hydrogen bonds into dimers, which are subsequently linked by further C-H⋯O inter-actions, building a three-dimensional network.

| S-EPMC3770420 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of 1-{[2-oxo-3-(prop-1-en-2-yl)-2,3-dihydro-1H-1,3-benzodiazol-1-yl]methyl}-3-(prop-1-en-2-yl)-2,3-dihydro-1H-1,3-benzodiazol-2-one.

Project description:In the title compound, C21H20N4O2, the intramolecular C—H?O hydrogen-bonded benzodiazolone moieties are planar to within 0.017?(1) and 0.026?(1)?Å, and are oriented at a dihedral angle of 57.35?(3)°. In the crystal, two sets of intermolecular C—H?O hydrogen bonds generate layers parallel to the bc plane. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H?H (51.8%), H?C/C?H (30.7%) and H?O/O?H (11.2%) interactions.

| S-EPMC6281105 | biostudies-other

5-Nitro-1-(prop-2-yn-1-yl)-2,3-dihydro-1H-1,3-benzodiazol-2-one.

Project description:In the two independent mol-ecules of the title compound, C(10)H(7)N(3)O(3), the nitro substitutent is twisted slightly with respect to the benzodiazol fused-ring system [dihedral angles = 4.9?(3) and 8.5?(1)°]. The two independent mol-ecules are disposed about a pseudo inversion center and are held together by N-H?O hydrogen bonds. The supramolecular dimer is essentially planar [dihedral angle between the fused rings = 2.0?(1)°]. Adjacent dimers are linked by acetyl-ene-nitro C-H?O inter-actions, generating a ribbon motif along (110).

| S-EPMC3344170 | biostudies-other

Crystal structure, Hirshfeld surface analysis and inter-action energy and DFT studies of 1-methyl-3-(prop-2-yn-1-yl)-2,3-di-hydro-1<i>H</i>-1,3-benzo-diazol-2-one.

Project description:In the title mol-ecule, C11H10N2O, the di-hydro-benzimidazol-2-one moiety is essentially planar, with the prop-2-yn-1-yl substituent rotated well out of this plane. In the crystal, C-HMthy⋯π(ring) inter-actions and C-HProp⋯ODhyr (Mthy = methyl, Prop = prop-2-yn-1-yl and Dhyr = di-hydro) hydrogen bonds form corrugated layers parallel to (10), which are associated through additional C-HBnz⋯ODhyr (Bnz = benzene) hydrogen bonds and head-to-tail, slipped, π-stacking [centroid-to-centroid distance = 3.7712 (7) Å] inter-actions between di-hydro-benzimidazol-2-one moieties. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H⋯H (44.1%), H⋯C/C⋯H (33.5%) and O⋯H/H⋯O (13.4%) inter-actions. Hydrogen-bonding and van der Waals inter-actions are the dominant inter-actions in the crystal packing. Computational chemistry calculations indicate that in the crystal, C-H⋯O hydrogen-bond energies are 46.8 and 32.5 (for C-HProp⋯ODhyr) and 20.2 (for C-HBnz⋯ODhyr) kJ mol-1. Density functional theory (DFT) optimized structures at the B3LYP/6-311 G(d,p) level are compared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.

| S-EPMC6895944 | biostudies-literature

Crystal structure of 1'-(prop-2-yn-1-yl)-1,4-di-hydro-spiro-[benzo[d][1,3]oxazine-2,3'-indolin]-2'-one.

Project description:In the title compound, C18H14N2O2, the six-membered oxazine ring adopts a half-chair conformation and its mean plane makes a dihedral angle of 83.23 (7)° with the pyrrolidine ring of the indoline ring system. In the crystal, mol-ecules are linked via N-H⋯O hydrogen bonds, forming chains along [100]. The chains are linked by C-H⋯π inter-actions, forming slabs parallel to (001).

| S-EPMC4518956 | biostudies-literature

1-(Prop-2-yn-yl)-1H-benzimidazol-2(3H)-one.

Project description:The benzimidazolone part of the title mol-ecule, C10H8N2O, is almost planar [r.m.s. deviation = 0.014?(1)?Å] and the NCH2C CH group forms a dihedral angle of 67.95?(6)° with its best plane. In the crystal, mol-ecules form inversion dimers via pairs of N-H?O hydrogen bonds. C-H?O inter-actions connect the dimers, forming a two-dimensional polymeric network parallel to (100).

| S-EPMC3588288 | biostudies-literature

Crystal structure, Hirshfeld surface analysis and inter-action energy and DFT studies of 5,5-diphenyl-1,3-bis-(prop-2-yn-1-yl)imidazolidine-2,4-dione.

Project description:The title compound, C21H16N2O2, consists of an imidazolidine unit linked to two phenyl rings and two prop-2-yn-1-yl moieties. The imidazolidine ring is oriented at dihedral angles of 79.10 (5) and 82.61 (5)° with respect to the phenyl rings, while the dihedral angle between the two phenyl rings is 62.06 (5)°. In the crystal, inter-molecular C-HProp⋯OImdzln (Prop = prop-2-yn-1-yl and Imdzln = imidazolidine) hydrogen bonds link the mol-ecules into infinite chains along the b-axis direction. Two weak C-HPhen⋯π inter-actions are also observed. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (43.3%), H⋯C/C⋯H (37.8%) and H⋯O/O⋯H (18.0%) inter-actions. Hydrogen bonding and van der Waals inter-actions are the dominant inter-actions in the crystal packing. Computational chemistry indicates that the C-HProp⋯OImdzln hydrogen-bond energy in the crystal is -40.7 kJ mol-1. Density functional theory (DFT) optimized structures at the B3LYP/6-311G(d,p) level are compared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.

| S-EPMC6659335 | biostudies-literature

Crystal structure, Hirshfeld surface analysis and density functional theory study of benzyl 2-oxo-1-(prop-2-yn-1-yl)-1,2-di-hydro-quinoline-4-carboxyl-ate.

Project description:The title mol-ecule, C20H15NO3, adopts a Z-shaped conformation with the carboxyl group nearly coplanar with the di-hydro-quinoline unit. In the crystal, corrugated layers are formed by C-H⋯O hydrogen bonds and are stacked by C-H⋯π(ring) inter-actions. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (43.3%), H⋯C/C⋯H (26.6%) and H⋯O/O⋯H (16.3%) inter-actions. The optimized structure calculated using density functional theory 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 4.0319 eV.

| S-EPMC8340981 | biostudies-literature