Browse
Submit Data
Databases
API
Help

Dataset Information

14 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Crystal structure of 2-amino-3-cyano-4-(4-meth-oxy-phen-yl)-4H-1-benzo-thieno[3,2-b]pyran.

ABSTRACT: The three fused five- and six-membered rings in the title compound, C19H14N2O2S, are virtually coplanar, with the maximum deviation from the mean plane being 0.060 (1) Å. This benzothieno[3,2-b]pyran ring system is nearly perpendic-ular to the plane of the 4-meth-oxy-phenyl ring, forming a dihedral angle of 83.65 (5)°. In the crystal, mol-ecules are linked by pairs of N-H⋯N hydrogen bonds into inversion dimers. The dimeric units are further connected by an N-H⋯O hydrogen bond into a tape running along the b axis. The tapes are linked together by C-H⋯N and π-π inter-actions [centroid-centroid distance = 3.7743 (8) Å], forming a three-dimensional network.

SUBMITTER: Bakhouch M

PROVIDER: S-EPMC4719970 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Crystal structure of ethyl 2-amino-4-(4-meth-oxy-phen-yl)-4H-1-benzothieno[3,2-b]pyran-3-carboxyl-ate.

Project description:The mol-ecule of the title compound, C21H19NO4S, features a fused ring system whereby a five-membered ring is flanked by two six-membered rings. This is linked to an ethyl 3-carboxyl-ate group and to a meth-oxy-benzene group. The fused-ring system is quasi-planar, with the greatest deviation from the mean plane being 0.131?(1)?Å for the methine C atom. The plane through the meth-oxy-benzene ring is nearly perpendicular to that through the fused-ring system, as indicated by the dihedral angle of 85.72?(6)°. An intra-molecular N-H?O hydrogen bond is noted. In the crystal, mol-ecules are linked by N-H?O hydrogen bonds, forming layers that stack along the a axis.

| S-EPMC4420120 | biostudies-literature

Ethyl 2-amino-4-phenyl-4H-1-benzo-thieno[3,2-b]pyran-3-carboxyl-ate.

Project description:The title heterocyclic compound, C(20)H(17)NO(3)S, was synthesized by condensation of ethyl cyano-acetate with (Z)-2-benzyl-idenebenzo[b]thio-phen-3(2H)-one in the presence of a basic catalyst in ethanol. The phenyl and ester groups make dihedral angles of 77.67?(6) and 8.52?(6)°, respectively, with the benzothienopyran ring system [maximum r.m.s. deviation = 0.1177?(13)?Å]. In the crystal, centrosymmetric dimers are formed through pairs of N-H?O hydrogen bonds between the amine and ester groups. Inter-molecular C-H?N hydrogen bonds and C-H?? inter-actions involving the thio-phene ring are also observed.

| S-EPMC3213548 | biostudies-literature

Crystal structures of two 4H-chromene derivatives: 2-amino-3-cyano-4-(3,4-di-chloro-phen-yl)-7-hy-droxy-4H-benzo[1,2-b]pyran 1,4-dioxane monosolvate and 2-amino-3-cyano-4-(2,6-di-chloro-phen-yl)-7-hy-droxy-4H-benzo[1,2-b]pyran.

Project description:In the title compounds, C16H9Cl2N2O2·C4H8O2 and C16H9Cl2N2O2, the bicyclic 4H-chromene cores are nearly planar with maximum deviations of 0.081?(2) and 0.087?(2)?Å. In both structures, the chromene derivative mol-ecules are linked into centrosymmetric dimers by pairs of N-H?O hydrogen bonds, forming R2 2 (16) motifs. These dimers are further linked in the 3,4-di-chloro-phenyl derivative by N-H?N hydrogen bonds into double layers parallel to (100) and in the 2,6-di-chloro-phenyl derivative by O-H?N hydrogen bonds into ribbons along the [10] direction. In the 3,4-di-chloro-phenyl derivative, the 1,4-dioxane solvent mol-ecules are connected to the chromene mol-ecules via O-H?O hydrogen bonds.

| S-EPMC6775756 | biostudies-literature

N'-[3-Cyano-4-(4-fluoro-phen-yl)-6-meth-oxy-4H-benzo[h]chromen-2-yl]-N,N-dimethyl-methanimidamide.

Project description:In the title compound, C24H20FN3O2, despite the 4H-pyran ring having a flattened half-chair conformation [the methine C atom lies 0.257?(3)?Å above the plane of the remaining atoms with an r.m.s. deviation of 0.0295?Å], the 14 non-H atoms of the 4H-benzo[h]chromene residue are approximately coplanar (r.m.s. deviation = 0.081?Å). The benzene ring is nearly perpendicular to this plane [dihedral angle = 76.18?(10)°], but the planar (r.m.s. deviation = 0.033?Å) dimethyl-methanimidamide substituent is coplanar [dihedral angle = 1.96?(12)°]. In the crystal, centrosymmetric dimeric aggregates arise from C-H?N inter-actions, and these are connected into supra-molecular layers in the ab plane by C-H?? and ?-? [inter-centroid (central C6 ring)?(outer C6 ring)(i) distance = 3.8564?(14)?Å] inter-actions.

| S-EPMC3629518 | biostudies-literature

Crystal structure of 2-amino-4-(4-meth-oxy-phen-yl)-4H-benzo[g]chromene-3-carbo-nitrile.

Project description:In the title compound, C21H16N2O2, the naphthalene fragment is twisted slightly, as indicated by the dihedral angle of 3.2?(2)° between the two six-membered rings. The pendant 4-meth-oxy-phenyl ring makes a dihedral angle of 86.08?(6)° with the central six-membered ring of the 4H-benzo[g]chromene ring system. In the crystal, mol-ecules are linked by pairs of N-H?N hydrogen bonds, forming inversion dimers which are linked into chains propagating in the b-axis direction by N-H?O hydrogen bonds.

| S-EPMC4719954 | biostudies-literature

4-(4-Meth-oxy-phen-yl)-6-methyl-amino-5-nitro-2-phenyl-4H-pyran-3-carbonitrile.

Project description:In the title compound, C20H17N3O4, the central pyran ring adopts a boat conformation with the O atom and diagonally opposite C atoms displaced by 0.1171?(1) and 0.1791?(1)?Å, respectively, from the mean plane defined by the other four atoms. The coplanar atoms of the pyran ring and the meth-oxy-benzene ring are nearly perpendicular, as evidenced by the dihedral angle 87.01?(1)°. The amine H atom forms an intra-molecular N-H?O(nitro) hydrogen bond. In the crystal, mol-ecules are linked into dimeric aggregates by N-H?O(nitro) hydrogen bonds, generating an R2(2)(12) graph-set motif.

| S-EPMC3588539 | biostudies-literature

Crystal structure of ethyl 2-amino-4-(4-chloro-phen-yl)-4H-1-benzothieno[3,2-b]pyran-3-carboxyl-ate.

Project description:The title compound, C20H16ClNO3S, is built up from three fused rings, one five- and two six-membered rings, linked to a 3-eth-oxy-carbonyl group and to a 4-chloro-phenyl ring. The hydropyran ring has a flattened envelope conformation, with the C atom substituted by the 4-chloro-phenyl ring as the flap (displaced by 0.077 (2) Å from the plane through the other atoms). The fused three-ring system is quasi-planar (r.m.s. deviation = 0.057 Å), with the largest deviation from the mean plane being 0.106 (1) Å for the C atom substituted by the 4-chloro-phenyl ring. The 4-chloro-phenyl ring is approximately perpendicular to the mean plane of the fused ring system, as indicated by the dihedral angle of 77.32 (6)° between their mean planes. There is an intra-molecular N-H⋯O hydrogen bond forming an S(6) ring motif. In the crystal, mol-ecules are linked by pairs of N-H⋯O hydrogen bonds, forming inversion dimers with an R 2 (2)(12) ring motif. There are also short inter-molecular Cl⋯O inter-actions present [3.1226 (12) Å] between neighbouring mol-ecules.

| S-EPMC4571428 | biostudies-literature

3-(3-Meth-oxy-phen-yl)benzo[d]thia-zolo[3,2-a]imidazol-9-ium hydrogen sulfate.

Project description:In the title mol-ecular salt, C(16)H(13)N(2)OS(+)·HSO(4) (-), the thia-zolo[3,2-a]benzimidazolium ring system is roughly planar [maximum deviation = 0.046?(3)?Å] and makes a dihedral angle of 58.22?(11)° with the benzene ring. The meth-oxy group is almost coplanar with its attached benzene ring [C(meth-yl)-O-C-C = -1.6?(5)°]. In the crystal, the cation is linked to the anion by a bifurcated N-H?(O,O) hydrogen bond, generating an R(1) (2)(4) ring motif. The ion pairs are then connected by a C-H?O hydrogen bond into inversion dimers and these dimers are further linked by O-H?O hydrogen bonds into an infinite tape along [100]. A ?-? stacking inter-action [centroid-to-centroid distance = 3.5738?(18)?Å] and a short inter-molecular contact [S?O = 2.830?(3)?Å] are also observed.

| S-EPMC3414329 | biostudies-literature

Ethyl 2-amino-4-(4-fluoro-phen-yl)-6-meth-oxy-4H-benzo[h]chromene-3-carboxyl-ate.

Project description:In the title compound, C(23)H(20)FNO(4), the fluoro-substituted benzene ring is approximately perpendicular to the mean plane of the 4H-benzo[h]chromene ring system [maximum deviation = 0.264?(1)?Å], with a dihedral angle of 83.79?(6)°. The pyran ring adopts a flattened boat conformation. The meth-oxy group is slightly twisted from the attached benzene ring of the 4H-benzo[h]chromene moiety [C-O-C-C = -2.1?(2)°]. An intra-molecular N-H?O hydrogen bond generates an S(6) ring motif. In the crystal, mol-ecules are linked by N-H?O and N-H?F hydrogen bonds into a layer parallel to the bc plane. The crystal packing also features C-H?? inter-actions.

| S-EPMC3379378 | biostudies-literature

Ethyl 2-amino-4-(4-bromo-phen-yl)-6-meth-oxy-4H-benzo[h]chromene-3-carboxyl-ate.

Project description:In the title compound, C23H20BrNO4, the pyran ring has a flattened boat conformation with the O and methine C atoms lying to one side of the plane [0.160?(5) and 0.256?(6)?Å, respectively] defined by the remaining atoms. Nevertheless, the 4H-benzo[h]chromene ring system approximates a plane (r.m.s. deviation = 0.116?Å) with the bromo-benzene ring almost perpendicular [dihedral angle = 83.27?(16)°] and the ester group coplanar [C-C-C-O = 3.4?(5)°]; the meth-oxy substituent is also coplanar [C-O-C-C = 174.5?(3)°]. In addition to an intra-molecular N-H?O(ester carbon-yl) hydrogen bond, the ester carbonyl O atom also forms an inter-molecular N-H?O hydrogen bond with the second amine H atom, generating a zigzag supra-molecular chain along the c axis in the crystal packing. The chains are linked into layers in the bc plane by N-H?Br hydrogen bonds, and these layers are consolidated into a three-dimensional architecture by C-H?? inter-actions.

| S-EPMC3588478 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

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