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

ABSTRACT: 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.

SUBMITTER: Mague JT

PROVIDER: S-EPMC4719954 | biostudies-literature | 2015 Dec

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.

Mague Joel T JT Mohamed Shaaban K SK Akkurt Mehmet M Younes Sabry H H SH Albayati Mustafa R MR

Acta crystallographica. Section E, Crystallographic communications 20151206 Pt 12

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. ...[more]

PMID: 26870473

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

Project description: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.

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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].

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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.

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

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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 π-π stacking inter-action is observed; the centroid-to-centroid distance is 3.7260 (7) Å.

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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.

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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.

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2-Amino-4-(4-fluoro-phen-yl)-6-meth-oxy-4H-benzo[h]chromene-3-carbonitrile.

Project description:In the title mol-ecule, C(21)H(15)FN(2)O(2), the dihedral angle between the fluoro-substituted benzene ring and the mean plane of the 4H-benzo[h]chromene ring system [maximum deviation = 0.109?(2)?Å] is 83.35?(7)°. The pyran ring adopts a slight sofa conformation with the tertiary C(H) atom forming the flap. The meth-oxy group is slightly twisted from the attached benzene ring of the 4H-benzo[h]chromene moiety [C-O-C-C = -4.3?(3)°]. In the crystal, mol-ecules are linked by inter-molecular N-H?N hydrogen bonds into infinite wave-like chains along the b axis. The crystal packing is further stabilized by ?-? inter-actions [centroid-centroid distance = 3.7713?(9)?Å].

| S-EPMC3379488 | biostudies-other

2-Amino-4-(4-bromo-phen-yl)-6-meth-oxy-4H-benzo[h]chromene-3-carbonitrile.

Project description:In the title compound, C21H15BrN2O2, the 14 non-H atoms of the 4H-benzo[h]chromene fused-ring system are approximately coplanar (r.m.s. deviation = 0.129?Å). Within this system, the 4H-pyran ring adopts a flattened half-chair conformation with the methine C atom lying 0.281?(4)?Å above the plane of the remaining atoms (r.m.s. deviation = 0.0446?Å). The bromo-benzene ring is almost perpendicular to the fused-ring system [dihedral angle = 85.34?(13)°]. In the crystal, supra-molecular layers parallel to (101) are sustained by amine-cyano N-H?N and amine-meth-oxy N-H?O hydrogen bonds. The layers stack with inter-actions of the type (bromo-benzene)C-H??(outer-C6 ring of the fused-ring system) connecting them.

| S-EPMC3629517 | biostudies-other

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.

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