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Crystal structure of 3-amino-1-(4-meth-oxy-phen-yl)-1H-benzo[f]chromene-2-carbo-nitrile.

ABSTRACT: In the title compound, C21H16N2O2, the meth-oxy-benzene ring is almost perpendicular to the mean plane of the naphthalene ring system, making a dihedral angle of 83.62 (5)°. The 4H-pyran ring fused with the naphthalene ring system is almost planar [maximum deviation = 0.033 (1) Å]. In the crystal, mol-ecules are linked into inversion dimers by pairs of N-H⋯N hydrogen bonds. N-H⋯O hydrogen bonds connect the dimers, forming a helical supra-molecular chain along the a-axis direction. The crystal packing also features C-H⋯π inter-actions.

SUBMITTER: Mohamed SK

PROVIDER: S-EPMC4518947 | biostudies-literature |

REPOSITORIES: biostudies-literature

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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

Crystal structure of 3-amino-1-(4-chloro-phen-yl)-1H-benzo[f]chromene-2-carbo-nitrile.

Project description:In the title compound, C20H13ClN2O, the chloro-benzene ring is almost perpendicular to the mean plane of the naphthalene ring system, making a dihedral angle of 81.26 (8)°. The 4H-pyran ring fused with the naphthalene ring system has a flattened boat conformation. In the crystal, N-H⋯N hydrogen bonds generate chains along the b-axis direction. Further N-H⋯N hydrogen bonds link these chains into sheets parallel to (010). The crystal packing also features C-H⋯π inter-actions. The crystal studied was an inversion twin with a 0.557 (16):0.443 (16) domain ratio.

| S-EPMC4518915 | biostudies-literature

Crystal structure of 3-amino-1-(4-hy-droxy-phen-yl)-1H-benzo[f]chromene-2-carbo-nitrile.

Project description:In the title compound, C20H14N2O2, the hy-droxy-benzene ring is almost perpendicular to the mean plane of the naphthalene ring system, making a dihedral angle of 85.56?(4)°. The 4H-pyran ring fused with the naphthalene ring system has a flattened boat conformation. In the crystal, O-H?N and N-H?O hydrogen bonds link the mol-ecules into a supra-molecular layer in the bc plane; N-H?? inter-actions also contribute to this arrangement. The layers are linked by weak by C-H?? and ?-? [inter-centroid separation = 3.8713?(7)?Å] inter-actions.

| S-EPMC4571384 | biostudies-other

Crystal structure of 2-amino-4-phenyl-4H-benzo[h]chromene-3-carbo-nitrile.

Project description:In the title compound, C20H14N2O, the plane of the phenyl ring is almost normal to that of the naphthalene ring system, forming a dihedral angle of 83.15 (8)°. The 4H-pyran ring fused with the naphthalene ring system has a flattened boat conformation. In the crystal, mol-ecules are linked by pairs of N-H⋯N hydrogen bonds, forming inversion dimers with an R 2 (2)(12) ring motif. The dimers are connected by C-H⋯π inter-actions, forming supra-molecular chains along [010].

| S-EPMC4518988 | biostudies-literature

3-Amino-1-(4-fluoro-phen-yl)-7-meth-oxy-1H-benzo[f]chromene-2-carbonitrile.

Project description:In the title compound, C21H15FN2O2, the furan ring has a flattened half-chair conformation [the methine C atom lies 0.136?(2)?Å above the C5 plane which has an r.m.s. deviation of 0.0229?Å]. Overall, the 1H-benzo[f]chromene fused-ring system approximates a plane (r.m.s. deviation of the 14 non-H atoms = 0.049?Å). The fluoro-benzene ring is almost perpendicular to this plane [dihedral angle = 89.58?(8)°]. Zigzag supra-molecular tapes along the b axis are the most notable feature of the crystal packing. This arises through an alternating sequence of 12-membered {?HNC3N}2 and eight-membered {?HNCO}2 synthons. These are connected into a three-dimensional architecture by ?-? [inter-centroid distance for centrosymmetrically related fluoro-benzene rings = 3.5181?(10)?Å] and C-H?? inter-actions.

| S-EPMC3629516 | biostudies-literature

3-Amino-1-(4-fluoro-phen-yl)-8-meth-oxy-1H-benzo[f]chromene-2-carbonitrile.

Project description:The title compound, C21H15FN2O2, features an approximately planar 1H-benzo[f]chromene fused-ring system (r.m.s. deviation for the 14 non-H atoms = 0.052?Å), with the fluoro-benzene ring being almost perpendicular to this [dihedral angle = 85.30?(7) °]. The furan ring has a flattened half-chair conformation, with the methine C atom deviating by 0.132?(2)?Å from the plane of the remaining atoms (r.m.s. deviation = 0.0107?Å). In the crystal, inversion dimers are formed via pairs of amine-cyano N-H?N hydrogen bonds. The dimers are connected into a three-dimensional architecture by C-H?N(cyano), C-H?? and ?-? [inter-centroid distance = 3.6671?(10)?Å] inter-actions.

| S-EPMC3629515 | 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?? inter-actions and ?-? stacking inter-actions between pyridine rings, with a centroid-centroid distance of 3.6448?(6)?Å, are observed.

| S-EPMC3790375 | biostudies-literature

Crystal structure of 2-amino-7-hy-droxy-4-(4-hy-droxy-phen-yl)-4H-chromene-3-carbo-nitrile.

Project description:In the title compound, C16H12N2O3, the chromene ring system is nearly planar [maximum deviation from the mean plane = 0.057?(1)?Å], and is almost perpendicular to the benzene ring, with a dihedral angle of 85.29?(5)°. In the crystal, mol-ecules are linked by classical N-H?O, O-H?O and O-H?N hydrogen bonds, and weak C-H?O hydrogen bonds, forming a three-dimensional supra-molecular network. Furthermore, a weak ?-? stacking inter-action is observed; the centroid-to-centroid distance is 3.7260?(7)?Å.

| S-EPMC4571389 | 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?? and slipped parallel ?-? inter-actions [centroid-centroid distance = 3.6532?(3)?Å] into a three-dimensional structure.

| S-EPMC4257429 | biostudies-literature

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?? inter-actions between inversion-related mol-ecules result in the formation of linear double chains along the b-axis direction.

| S-EPMC4051075 | biostudies-literature

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