Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Crystal structures of three homologues with increasing ring size: 2-methoxy-4-(thiophen-2-yl)-5,6,7,8-tetrahydroquinoline-3-carbonitrile, 2-methoxy-4-(thiophen-2-yl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carbonitrile and 2-methoxy-4-(thiophen-2-yl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine-3-carbonitrile

ABSTRACT: The title compounds form a homologous but non-isotypic series with appreciable differences in molecular form. In each case, the packing is determined by two C—H⋯N hydrogen bonds. The title compounds, C15H14N2OS (1a), C16H16N2OS (1b), and C17H18N2OS (1c), form a homologous series in which the size of the saturated ring increases from six- to eight-membered (with four, five and six methylene groups respectively). For 1b and 1c, the central (CH2)n moieties are all displaced to the same side of their ring, and the CH2—CH2—CH2 angles are much wider than the standard sp3 value; a database search indicates that these are general features of such ring systems. For 1a, the thiophene ring lies with the sulfur atom on the opposite side of the Cthiophene—Cpyridine bond to the cyano group, in contrast to 1b and 1c. For each compound, the packing may be described in terms of two ‘weak’ C—H⋯N hydrogen bonds, which link the molecules to form one-dimensional (1a, 1c) or three-dimensional (1b) assemblies.

SUBMITTER: Hebishy A

PROVIDER: S-EPMC10088300 | biostudies-literature | 2023 Mar

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

4-(4-Meth-oxy-phen-yl)-2-oxo-1,2,5,6-tetra-hydro-benzo[h]quinoline-3-carbo-nitrile.

Project description:In the mol-ecule of the title compound, C(21)H(16)N(2)O(2), the tetra-hydro-benzo[h]quinoline fused-ring system is buckled owing to the ethyl-ene -CH(2)CH(2)- fragment, the benzene ring and the pyridine ring being twisted by 19.7?(1)°. The 4-substituted aromatic ring is bent away from the pyridine ring by 50.3?(1)° in order to avoid crowding the cyanide substituent. In the crystal, two mol-ecules are linked by a pair of N-H?O hydrogen bonds to form a centrosymmetric dimer.

| S-EPMC3200898 | biostudies-other

2-Meth-oxy-4-(2-meth-oxy-phen-yl)-5,6,7,8,9,10-hexa-hydro-cyclo-octa-[b]pyridine-3-carbo-nitrile.

Project description:In the title compound, C20H22N2O2, the central pyridine ring forms a dihedral angle of 76.32 (8)° with the pseudo-axial benzene ring. The cyclo-octane ring adopts a twisted boat chair conformation. In the crystal, weak inter-molecular C-H⋯π inter-actions between inversion-related mol-ecules result in the formation of linear double chains along the b-axis direction.

| S-EPMC4051075 | biostudies-literature

6-Meth-oxy-4-(2,4,5-tri-meth-oxy-phen-yl)-2,2'-bi-pyridine-5-carbo-nitrile.

Project description:In the title 3-cyano-pyridine derivative, C21H19N3O4, the 3-cyano-substituted pyridine ring forms dihedral angles of 2.35 (5) and 41.60 (5)° with the unsubstituted pyridine and 2,4,5-trimeth-oxy-substituted benzene rings, respectively. The dihedral angle between the unsubstituted pyridine and benzene rings is 39.84 (5)°. The meth-oxy groups form Cmeth-yl-O-C-(C,N) torsion angles in the range 0.80 (15)-11.45 (15)°. In the crystal, mol-ecules related by 21 screw axes are linked by weak C-H⋯N hydrogen bonds along [010]. In addition, weak C-H⋯π inter-actions and π-π stacking inter-actions between pyridine rings, with a centroid-centroid distance of 3.6448 (6) Å, are observed.

| S-EPMC3790375 | biostudies-literature

4-(2-Fluoro-phen-yl)-2-meth-oxy-5,6,7,8,9,10-hexa-hydro-cyclo-octa-[b]pyridine-3-carbo-nitrile.

Project description:In the title compound, C19H19FN2O, the cyclo-octene ring adopts a twisted boat-chair conformation. The dihedral angle between the plane of the fluorophenyl substituent and that of the pyridine ring is 76.39 (8)°. The F and ortho-H atoms of the fluoro-benzene ring are disordered, with occupancy factors of 0.226 (5) and 0.774 (5). In the crystal, no significant inter-actions are observed between the mol-ecules beyond van der Waals contacts.

| S-EPMC4158480 | biostudies-literature

Crystal structure of 2-benzyl-amino-4-(4-meth-oxy-phen-yl)-6,7,8,9-tetra-hydro-5H-cyclo-hepta-[b]pyridine-3-carbo-nitrile.

Project description:The title compound, C25H25N3O, comprises a 2-amino-pyridine ring fused with a cyclo-heptane ring, which adopts a chair conformation. The central pyridine ring (r.m.s. deviation = 0.013 Å) carries three substituents, viz. a benzyl-amino group, a meth-oxy-phenyl ring and a carbo-nitrile group. The N atom of the carbo-nitrile group is significantly displaced [by 0.2247 (1) Å] from the plane of the pyridine ring, probably due to steric crowding involving the adjacent substituents. The phenyl and benzene rings are inclined to one another by 58.91 (7)° and to the pyridine ring by 76.68 (7) and 49.80 (6)°, respectively. In the crystal, inversion dimers linked by pairs of N-H⋯Nnitrile hydrogen bonds generate R 2 (2)(14) loops. The dimers are linked by C-H⋯π and slipped parallel π-π inter-actions [centroid-centroid distance = 3.6532 (3) Å] into a three-dimensional structure.

| S-EPMC4257429 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of 2-amino-4-(4-meth-oxy-phen-yl)-6-oxo-1-phenyl-1,4,5,6-tetra-hydro-pyridine-3-carbo-nitrile.

Project description:The central tetra-hydro-pyridine ring of the title compound, C19H17N3O2, adopts a screw-boat conformation. In the crystal, strong C-H⋯O and N-H⋯N hydrogen bonds form dimers with R 2 2(14) and R 2 2(12) ring motifs, respectively, between consecutive mol-ecules along the c-axis direction. Inter-molecular N-H⋯O and C-H⋯O hydrogen bonds connect these dimers, forming a three-dimensional network. C-H⋯π inter-actions and π-π stacking inter-actions contribute to the stabilization of the mol-ecular packing. A Hirshfeld surface analysis indicates that the contributions from the most prevalent inter-actions are H⋯H (47.1%), C⋯H/H⋯C (20.9%), O⋯H/H⋯O (15.3%) and N⋯H/H⋯N (11.4%).

| S-EPMC8900505 | biostudies-literature

3-(4-Amino-phen-yl)-5-(4-meth-oxy-phen-yl)-4,5-di-hydro-1H-pyrazole-1-carbo-thio-amide.

Project description:In the mol-ecule of title pyrazoline derivative, C17H18N4OS, the pyrazole ring adopts an envelope conformation with the flap atom, which bears the meth-oxy-phenyl substituent, displaced by 0.0750?(12)?Å from the plane through the other ring atoms. The two substituted benzene rings make a dihedral angle of 70.59?(6)°. The meth-oxy group is twisted slightly with respect to the attached benzene ring [Cmeth-yl-O-C-C torsion angle = -8.84?(15)°]. An intra-molecular N-H?N hydrogen bond occurs. In the crystal, the pyrazoline mol-ecules are linked by N-H?O and N-H?S hydrogen bonds into zigzag layers parallel to the bc plane and stacked along the a axis by ?-? inter-actions with centroid-centroid distances of 3.4690?(7) and 3.5792?(7)?Å. C-H?? inter-actions are also present.

| S-EPMC3793732 | biostudies-literature

Crystal structures of 2-benzyl-amino-4-(4-bromo-phen-yl)-6,7,8,9-tetra-hydro-5H-cyclo-hepta-[b]pyridine-3-carbo-nitrile and 2-benzyl-amino-4-(4-chloro-phen-yl)-6,7,8,9-tetra-hydro-5H-cyclo-hepta[b]pyridine-3-carbo-nitrile.

Project description:In the title compounds, C24H22BrN3, (I), and C24H22ClN3, (II), the 2-amino-pyridine ring is fused with a cyclo-heptane ring, which adopts a half-chair conformation. The planes of the phenyl and benzene rings are inclined to that of the central pyridine ring [r.m.s. deviations = 0.0083 (1) and 0.0093 (1) Å for (I) and (II), respectively] by 62.47 (17) and 72.51 (14)°, respectively, in (I), and by 71.44 (9) and 54.90 (8)°, respectively, in (II). The planes of the aromatic rings are inclined to one another by 53.82 (17)° in (I) and by 58.04 (9)° in (II). In the crystals of both (I) and (II), pairs of N-H⋯Nnitrile hydrogen bonds link the mol-ecules, forming inversion dimers with R 2 (2)(12) ring motifs. In (I), the resulting dimers are connected through C-H⋯Br hydrogen bonds, forming sheets parallel to (10-1), and π-π inter-actions [inter-centroid distance = 3.7821 (16) Å] involving inversion-related pyridine rings, forming a three-dimensional network. In (II), the resulting dimers are connected through π-π inter-actions [inter-centroid distance = 3.771 (2) Å] involving inversion-related pyridine rings, forming a two-dimensional network lying parallel to (001).

| S-EPMC4331894 | biostudies-literature

Crystal structure of 4-(1H-indol-3-yl)-2-(4-meth-oxy-phen-yl)-6-phenyl-pyridine-3-carbo-nitrile.

Project description:In the title compound, C27H19N3O, the dihedral angles between the plane of the pyridine ring and those of the indole (r.m.s. deviation = 0.018 Å), phenyl and meth-oxy-benzene substituents are 33.60 (6), 25.28 (7) and 49.31 (7)°, respectively. The N atom of the carbo-nitrile group is significantly displaced [0.288 (2) Å] from the plane of the pyridine ring, perhaps due to steric crowding. In the crystal, inversion dimers linked by pairs of N-H⋯Nn (n = nitrile) hydrogen bonds generate R 2 (2)(16) loops. Aromatic π-π stacking [centroid-centroid separation = 3.6906 (7) Å] and very weak C-H⋯π inter-actions are also observed".

| S-EPMC4257225 | biostudies-literature

2-(4-Bromo-phen-yl)-4-(4-meth-oxy-phen-yl)-6,7,8,9-tetra-hydro-5H-cyclo-hepta-[b]pyridine.

Project description:In the title compound, C23H22BrNO, the cyclo-heptane ring adopts a chair conformation. The pyridine ring makes dihedral angles of 58.63 (15) and 8.27 (16)° with the benzene rings. The dihedral angle between the benzene rings is 56.68 (17)°. The crystal packing features C-Br⋯π inter-actions [Br⋯centroid distances= 3.813 (2) and 3.839 (2) Å; C-Br⋯centroid = 126.25 (10) and 138.31 (10)°, respectively, forming a three dimensional supramolecular architecture.

| S-EPMC3685096 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data