1-[(4-Chlorophenyl)(phenylimino)methyl]-7-methoxy-2-naphthol–1,4-diazabicyclo[2.2.2]octane (2/1)

Nagasawa, Atsushi; Mitsui, Ryosuke; Kato, Yuichi; Okamoto, Akiko; Yonezawa, Noriyuki

doi:10.1107/s1600536810034690

Cited by 2 publications

(1 citation statement)

References 8 publications

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“…However, the spatial organization of triarylimine 3 based on perpendicular arrangement of aromatic rings is essentially same to that of precursor ketone 1. Figure 2 shows the single molecular structures of methyl ether-cleaved 1-aroylnaphthalene (5) originated triarylimine (6) [30] in crystal. Though preparation of satisfactorily qualified crystal for X-ray crystal analysis of N-(4-methoxyphenoxy)imine compound 4 was unsuccessful, the crystal structure of analogous imine compound (6) was determined.…”

Section: X-ray Crystallographymentioning

confidence: 99%

Crystal Structure Study on Non-Coplanarly Organized Accumulating Aromatic Rings Molecules: Spatial Organization of C,C,N-Triaryl Substituted Imines

Okamoto

Nagasawa²,

nbsp³

et al. 2013

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The X-ray crystal structures of C,C,N-triaryl-substituted imine compounds, which have methoxy or hydroxy group adjacent to the imino moiety, are reported and discussed in comparison with those of the precursor ketone compounds, 1-(4-chlorobenzoyl)-2,7-dimethoxynaphthalene and 1-(4-chlorobenzoyl)-2-hydroxy-7-methoxynaphthalene. In crystals, three aromatic rings in a molecule of the methyl ether-retained imine compound are positioned almost perpendicularly to each other by giving non-coplanar spatial organization of the single molecular structure [dihedral angles: 85.32(18)˚ for Clinked phenyl ring and naphthalene ring; 79.27(17)˚ for N-linked phenyl ring and naphthalene ring; 84.78(17)˚ for Clinked phenyl ring and N-linked phenyl ring]. Spatial organization of the analogous methyl ether-cleaved imine compound has essentially same topology [dihedral angles 80.39(6)˚ for the Clinked phenyl ring and naphthalene ring; 82.35(6)˚ for the N-linked phenyl ring and naphthalene ring; 87.09(7)˚ for C-and N-linked phenyl rings]. These structural features of triarylimines apparently differ from those of the precursor ketones. Two aromatic rings in the methyl ether-cleaved ketone compound make smaller dihedral angle [58.10(6)˚] by intramolecular hydrogen bond between ketonic carbonyl group and hydroxy group [2.5573(16) Å] than that of the methyl ether-retained ketone [72.06(7)˚]. In molecular packing, the methyl ether-retained imine forms tubular molecular alignments composed of R-S dimeric molecular pairs, whereas the methyl ether-retained ketone affords consecutively stacks of one configurated molecules.

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Section: X-ray Crystallographymentioning

confidence: 99%

Crystal Structure Study on Non-Coplanarly Organized Accumulating Aromatic Rings Molecules: Spatial Organization of C,C,N-Triaryl Substituted Imines

Okamoto

Nagasawa²,

nbsp³

et al. 2013

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7-Methoxy-1-{[(Z)-2-nitrophenylimino](phenyl)methyl}-2-naphthol chloroform monosolvate

2010

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In the title compound, C24H18N2O4·CHCl3, the phenyl and benzene rings make a dihedral angle of 38.60 (9)° and connect in an orientation almost perpendicular to the naphthalene ring system at dihedral angles of 78.73 (8) and 81.20 (7)°. The molecule has a Z configuration about the C=N bond. In the crystal, molecules are linked by intermolecular O—H⋯N=C hydrogen bonds between the imino moiety and hydroxy groups. Intermolecular C—Cl⋯C interactions between Cl atoms of the CHCl3 molecule and C atoms of the naphthalene rings are also present [Cl⋯C = 3.353 (2) and 3.326 (19) Å]. The nitro group and the chloroform solvent molecule are disordered over two positions with site occupancies of 0.884 (4) and 0.116 (4).

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1-[(4-Chlorophenyl)(phenylimino)methyl]-7-methoxy-2-naphthol–1,4-diazabicyclo[2.2.2]octane (2/1)

Cited by 2 publications

References 8 publications

Crystal Structure Study on Non-Coplanarly Organized Accumulating Aromatic Rings Molecules: Spatial Organization of <i>C</i>,<i>C</i>,<i>N</i>-Triaryl Substituted Imines

Crystal Structure Study on Non-Coplanarly Organized Accumulating Aromatic Rings Molecules: Spatial Organization of <i>C</i>,<i>C</i>,<i>N</i>-Triaryl Substituted Imines

7-Methoxy-1-{[(Z)-2-nitrophenylimino](phenyl)methyl}-2-naphthol chloroform monosolvate

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1-[(4-Chlorophenyl)(phenylimino)methyl]-7-methoxy-2-naphthol–1,4-diazabicyclo[2.2.2]octane (2/1)

Cited by 2 publications

References 8 publications

Crystal Structure Study on Non-Coplanarly Organized Accumulating Aromatic Rings Molecules: Spatial Organization of &lt;i&gt;C&lt;/i&gt;,&lt;i&gt;C&lt;/i&gt;,&lt;i&gt;N&lt;/i&gt;-Triaryl Substituted Imines

Crystal Structure Study on Non-Coplanarly Organized Accumulating Aromatic Rings Molecules: Spatial Organization of &lt;i&gt;C&lt;/i&gt;,&lt;i&gt;C&lt;/i&gt;,&lt;i&gt;N&lt;/i&gt;-Triaryl Substituted Imines

7-Methoxy-1-{[(Z)-2-nitrophenylimino](phenyl)methyl}-2-naphthol chloroform monosolvate

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Crystal Structure Study on Non-Coplanarly Organized Accumulating Aromatic Rings Molecules: Spatial Organization of <i>C</i>,<i>C</i>,<i>N</i>-Triaryl Substituted Imines

Crystal Structure Study on Non-Coplanarly Organized Accumulating Aromatic Rings Molecules: Spatial Organization of <i>C</i>,<i>C</i>,<i>N</i>-Triaryl Substituted Imines