Crystal structure of 1-(4-hydroxybenzoyl)-2,7-dimethoxynaphthalene: Contribution of classical and non-classical hydrogen bonding interactions to the molecular packing structure

Okamoto, Akiko; Muto, Toyokazu; Gaowa, Siqin; Takahara, Genta; Yonezawa, Noriyuki

doi:10.5155/eurjchem.8.1.33-41.1529

Cited by 5 publications

(1 citation statement)

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“…The authors' recent work has focused on peri-aroylnaphthalene compounds and the homologous/analogous substances. [11][12][13][14][15][16][17][18][19][20] According to the X-ray crystal structural analyses of ninety peri-aroylnaphthalene compounds, the two aroyl groups are non-coplanarly situated to the naphthalene ring and ordinary oriented in an opposite direction (anti-orientation). The molecular packing of peri-aroylnaphthalene compounds are mainly stabilized by cooperation of several kinds of weak non-covalent-bonding interactions, i.e., four kinds of nonclassical hydrogen bonds, (sp 2 )C-H···O=C hydrogen bond, (sp 3 )C-H···O=C hydrogen bond, (sp 3 )C-H···OR hydrogen bond, and C-H···π hydrogen-bonding interaction, and π···π stacking interaction are observed in decreasing order of frequency.…”

Section: Introductionmentioning

confidence: 99%

Crystal Structure of (1r,2s)-1,2-Bis(4-Chlorophenyl)-3,8-Dimethoxyacenaphthene-1,2-Diol: Tetrameric String of Four Conformers Connected by Classical Hydrogen Bonds and Molecular Accumulation Alignment by Linking of the Tetramers With the Aid of Non-Classi

Mido

Iitsuka

Yokoyama

et al. 2017

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Keywords: S-shaped tetramer composed of four conformers, pseudo-centrosymmetricity, classical hydrogen bonds, non-classical hydrogen bondsCrystal structure of (1R,2S)-1,2-bis(4-chlorophenyl)-3,8-dimethoxyacenaphthene-1,2-diol, C26H20O4Cl2, is reported and discussed from the viewpoints of characteristics in spatial organization, i.e., single molecular structures of four conformers, tetrameric aggregates, and higher ordered structures, with clarification of a classical and two non-classical hydrogen bonding interactions as the structure determining interactions. The title compound crystallizes with four independent molecules (conformers G, B, R, and Y) in the asymmetric unit. Furthermore, each independent molecule displays a meso configuration, with one 4-chlorophenyl group R and the other S. The four molecules are related by inversion center in the asymmetric unit of P-1 space group, exhibiting the number of molecules is eight, Z = 8. Single molecular structure of each conformer shows that the two benzene rings are bonded with large dihedral angles against the naphthalene plane and the two phenyl rings are oriented in the same direction with respect to the naphthalene ring plane (syn-orientation). The four conformers are classified into two groups according to overlapping feature of phenyl rings, i.e., conformers G and Y have larger slippage of the phenyl rings than conformers B and R. In the molecular packing, four conformers Y, B, R, and G are connected by classical O-H…O(H) hydrogen bonds in head-to-head fashion forming S-shaped tetramer. Tetramers composed of four conformers are stacked into columnar structure along a-axis through non-classical C-H…Cl hydrogen bonds between conformers G. The columns are linked into a sheet structure by non-classical C-H…Cl hydrogen bonds between conformers G and Y along ab-diagonal. The waved sheets are interlocked by two types of non-classical C-H… hydrogen bonds forming the stripe structure along c-axis, i.e., non-classical C-H… hydrogen bonds between conformers R and Y, and those between conformers B and G.

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Section: Introductionmentioning

confidence: 99%

Crystal Structure of (1r,2s)-1,2-Bis(4-Chlorophenyl)-3,8-Dimethoxyacenaphthene-1,2-Diol: Tetrameric String of Four Conformers Connected by Classical Hydrogen Bonds and Molecular Accumulation Alignment by Linking of the Tetramers With the Aid of Non-Classi

Mido

Iitsuka

Yokoyama

et al. 2017

ECB

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Ketone-hybridized Cyclic Water Hexamer with Chair-conformation in Crystal of Macrocyclic peri-Aroylnaphthalene Compound

et al. 2019

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Fluoro Group Pivoting Dual Hydrogen Bonding Intramolecular Bridge for 1,2-Bis(2-fluorophenyl)acenaphthenediol Molecule in Solution: NMR Spectrometrical Confirmation of Simultaneous Participation of F–C(sp²) Group to Through-space-couplings with Aromatic and Hydroxy Hydrogen Atoms

et al. 2020

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Crystal structure of 1-(4-hydroxybenzoyl)-2,7-dimethoxynaphthalene: Contribution of classical and non-classical hydrogen bonding interactions to the molecular packing structure

Cited by 5 publications

References 21 publications

Crystal Structure of (1r,2s)-1,2-Bis(4-Chlorophenyl)-3,8-Dimethoxyacenaphthene-1,2-Diol: Tetrameric String of Four Conformers Connected by Classical Hydrogen Bonds and Molecular Accumulation Alignment by Linking of the Tetramers With the Aid of Non-Classi

Crystal Structure of (1r,2s)-1,2-Bis(4-Chlorophenyl)-3,8-Dimethoxyacenaphthene-1,2-Diol: Tetrameric String of Four Conformers Connected by Classical Hydrogen Bonds and Molecular Accumulation Alignment by Linking of the Tetramers With the Aid of Non-Classi

Ketone-hybridized Cyclic Water Hexamer with Chair-conformation in Crystal of Macrocyclic peri-Aroylnaphthalene Compound

Fluoro Group Pivoting Dual Hydrogen Bonding Intramolecular Bridge for 1,2-Bis(2-fluorophenyl)acenaphthenediol Molecule in Solution: NMR Spectrometrical Confirmation of Simultaneous Participation of F–C(sp²) Group to Through-space-couplings with Aromatic and Hydroxy Hydrogen Atoms

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Crystal structure of 1-(4-hydroxybenzoyl)-2,7-dimethoxynaphthalene: Contribution of classical and non-classical hydrogen bonding interactions to the molecular packing structure

Cited by 5 publications

References 21 publications

Crystal Structure of (1r,2s)-1,2-Bis(4-Chlorophenyl)-3,8-Dimethoxyacenaphthene-1,2-Diol: Tetrameric String of Four Conformers Connected by Classical Hydrogen Bonds and Molecular Accumulation Alignment by Linking of the Tetramers With the Aid of Non-Classi

Crystal Structure of (1r,2s)-1,2-Bis(4-Chlorophenyl)-3,8-Dimethoxyacenaphthene-1,2-Diol: Tetrameric String of Four Conformers Connected by Classical Hydrogen Bonds and Molecular Accumulation Alignment by Linking of the Tetramers With the Aid of Non-Classi

Ketone-hybridized Cyclic Water Hexamer with Chair-conformation in Crystal of Macrocyclic peri-Aroylnaphthalene Compound

Fluoro Group Pivoting Dual Hydrogen Bonding Intramolecular Bridge for 1,2-Bis(2-fluorophenyl)acenaphthenediol Molecule in Solution: NMR Spectrometrical Confirmation of Simultaneous Participation of F–C(sp2) Group to Through-space-couplings with Aromatic and Hydroxy Hydrogen Atoms

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Fluoro Group Pivoting Dual Hydrogen Bonding Intramolecular Bridge for 1,2-Bis(2-fluorophenyl)acenaphthenediol Molecule in Solution: NMR Spectrometrical Confirmation of Simultaneous Participation of F–C(sp²) Group to Through-space-couplings with Aromatic and Hydroxy Hydrogen Atoms