E-ISSN 2063-5346
 

Research Article 
ECB. 2017; 6(7): 273-280


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 THETETRAMERS WITH THE AID OF NON-CLASSICAL HYDROGEN BONDS

Takahiro Mido, Hiroaki Iitsuka, Takeshi Yokoyama, Genta Takahara, Kazuki Ogata, Noriyuki Yonezawa, Akiko Okamoto.

Abstract
Crystal 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.

Key words: S-shaped tetramer composed of four conformers, pseudo-centrosymmetricity, classical hydrogen bonds, non-classical hydrogen bonds


 
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How to Cite this Article
Pubmed Style

Takahiro Mido, Hiroaki Iitsuka, Takeshi Yokoyama, Genta Takahara, Kazuki Ogata, Noriyuki Yonezawa, Akiko Okamoto. 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 THETETRAMERS WITH THE AID OF NON-CLASSICAL HYDROGEN BONDS . ECB. 2017; 6(7): 273-280.


Web Style

Takahiro Mido, Hiroaki Iitsuka, Takeshi Yokoyama, Genta Takahara, Kazuki Ogata, Noriyuki Yonezawa, Akiko Okamoto. 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 THETETRAMERS WITH THE AID OF NON-CLASSICAL HYDROGEN BONDS . https://www.eurchembull.com/?mno=41364 [Access: August 10, 2022].


AMA (American Medical Association) Style

Takahiro Mido, Hiroaki Iitsuka, Takeshi Yokoyama, Genta Takahara, Kazuki Ogata, Noriyuki Yonezawa, Akiko Okamoto. 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 THETETRAMERS WITH THE AID OF NON-CLASSICAL HYDROGEN BONDS . ECB. 2017; 6(7): 273-280.



Vancouver/ICMJE Style

Takahiro Mido, Hiroaki Iitsuka, Takeshi Yokoyama, Genta Takahara, Kazuki Ogata, Noriyuki Yonezawa, Akiko Okamoto. 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 THETETRAMERS WITH THE AID OF NON-CLASSICAL HYDROGEN BONDS . ECB. (2017), [cited August 10, 2022]; 6(7): 273-280.



Harvard Style

Takahiro Mido, Hiroaki Iitsuka, Takeshi Yokoyama, Genta Takahara, Kazuki Ogata, Noriyuki Yonezawa, Akiko Okamoto (2017) 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 THETETRAMERS WITH THE AID OF NON-CLASSICAL HYDROGEN BONDS . ECB, 6 (7), 273-280.



Turabian Style

Takahiro Mido, Hiroaki Iitsuka, Takeshi Yokoyama, Genta Takahara, Kazuki Ogata, Noriyuki Yonezawa, Akiko Okamoto. 2017. 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 THETETRAMERS WITH THE AID OF NON-CLASSICAL HYDROGEN BONDS . European Chemical Bulletin, 6 (7), 273-280.



Chicago Style

Takahiro Mido, Hiroaki Iitsuka, Takeshi Yokoyama, Genta Takahara, Kazuki Ogata, Noriyuki Yonezawa, Akiko Okamoto. "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 THETETRAMERS WITH THE AID OF NON-CLASSICAL HYDROGEN BONDS ." European Chemical Bulletin 6 (2017), 273-280.



MLA (The Modern Language Association) Style

Takahiro Mido, Hiroaki Iitsuka, Takeshi Yokoyama, Genta Takahara, Kazuki Ogata, Noriyuki Yonezawa, Akiko Okamoto. "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 THETETRAMERS WITH THE AID OF NON-CLASSICAL HYDROGEN BONDS ." European Chemical Bulletin 6.7 (2017), 273-280. Print.



APA (American Psychological Association) Style

Takahiro Mido, Hiroaki Iitsuka, Takeshi Yokoyama, Genta Takahara, Kazuki Ogata, Noriyuki Yonezawa, Akiko Okamoto (2017) 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 THETETRAMERS WITH THE AID OF NON-CLASSICAL HYDROGEN BONDS . European Chemical Bulletin, 6 (7), 273-280.