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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

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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

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

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

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

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