[2,7-Dibutoxy-8-(4-fluorobenzoyl)naphthalen-1-yl](4-fluorophenyl)methanone

Hijikata, Daichi; Sasagawa, Kosuke; Yoshiwaka, Sayaka; Okamoto, Akiko; Yonezawa, Noriyuki

doi:10.1107/s1600536812044923

Acta Cryst E

2012

DOI: 10.1107/s1600536812044923

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[2,7-Dibutoxy-8-(4-fluorobenzoyl)naphthalen-1-yl](4-fluorophenyl)methanone

Daichi Hijikata¹,

Kosuke Sasagawa²,

Sayaka Yoshiwaka³

et al.

Abstract: In the title compound, C32H30F2O4, the benzene rings of the benzoyl groups make dihedral angles of 74.55 (6) and 74.39 (7)° with the naphthalene ring system. In the crystal, intra- and intermolecular C—H⋯π interactions are observed between the butoxy group and the aromatic rings. There are also C—H⋯F hydrogen bonds present that link the molecules into chains propagating along [010].

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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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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

CSTA

Self Cite

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[2,7-Dibutoxy-8-(4-fluorobenzoyl)naphthalen-1-yl](4-fluorophenyl)methanone

Cited by 1 publication

References 7 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

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[2,7-Dibutoxy-8-(4-fluorobenzoyl)naphthalen-1-yl](4-fluorophenyl)methanone

Cited by 1 publication

References 7 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

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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