European Journal of Chemistry 2021, 12(2), 147-153 | doi: https://doi.org/10.5155/eurjchem.12.2.147-153.2114 | Get rights and content

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Crystal structure of bis(1,8-dibenzoyl-7-methoxynaphthalen-2-yl)terephthalate: Terephthalate phenylene moiety acts as bidentate hydrogen acceptor of bidirectional C-H···π non-classical hydrogen bonds


Kikuko Iida (1) orcid , Rei Sakamoto (2) orcid , Kun Li (3) orcid , Miyuki Kobayashi (4) orcid , Hiroaki Iitsuka (5) orcid , Noriyuki Yonezawa (6) orcid , Akiko Okamoto (7,*) orcid

(1) Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture and Technology, 2-24-16 Nakamachi, Koganei, Tokyo, 184-8588, Japan
(2) Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture and Technology, 2-24-16 Nakamachi, Koganei, Tokyo, 184-8588, Japan
(3) Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture and Technology, 2-24-16 Nakamachi, Koganei, Tokyo, 184-8588, Japan
(4) Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture and Technology, 2-24-16 Nakamachi, Koganei, Tokyo, 184-8588, Japan
(5) Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture and Technology, 2-24-16 Nakamachi, Koganei, Tokyo, 184-8588, Japan
(6) Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture and Technology, 2-24-16 Nakamachi, Koganei, Tokyo, 184-8588, Japan
(7) Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture and Technology, 2-24-16 Nakamachi, Koganei, Tokyo, 184-8588, Japan
(*) Corresponding Author

Received: 01 Mar 2021 | Revised: 16 Apr 2021 | Accepted: 17 Apr 2021 | Published: 30 Jun 2021 | Issue Date: June 2021

Abstract


The title compound lies about a crystallographic inversion centre located at the terephthalate moiety. The two peri-benzoylnaphthalene units having atrope chirality are also situated centrosymmetrically. In the two peri-benzoylnaphthalene moieties, two benzoyl groups are substituted at 1 and 8 carbons of the naphthalene ring in anti-orientation. Then two absolute configurations of peri-benzoylnaphthalene moieties are consequently assigned as complementary to each other, i.e., one unit has R,R-configuration and the other S,S-one, respectively. The two benzoyl groups in peri-benzoylnaphthalene moiety and the terephthalate phenylene ring are non-coplanarly located against the naphthalene ring. The dihedral angles of each benzene ring of two benzoyl groups and terephthalate unit with the naphthalene ring are 73.73 and 75.96, and 71.79°. In molecular packing, several kinds of weak interactions are responsible to induce three-dimensional molecular network. Especially, the synergetic effect realized through the bidentate hydrogen acceptor function in bidirectional C-H···π non-classical hydrogen bonds by the terephthalate phenylene ring moiety plausibly plays the determining role.


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European Journal of Chemistry

Keywords


Aggregation; Weak interactions; Conformation analysis; Aromatic ring structure; Bidentate hydrogen acceptor; Bidirectional C-H···π interactions

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DOI: 10.5155/eurjchem.12.2.147-153.2114

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Funding information


Tokyo Ohka Foundation for The Promotion of Science and Technology and JSPS KAKENHI Grant No. JP20K05473, Japan

Citations

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[1]. M. Kobayashi, R. Sakamoto, P. Zhang, Y. Zhao, K. Li, K. Noguchi, N. Yonezawa, A. Okamoto
Packing structure and non-classical hydrogen bonding interactions of the toluene solvate crystal of 1,8-bis(4-methylbenzoyl)naphthalene-2,7-diyl dibenzoate: Role of toluene molecule in determination of the spatial arrangement of the major constituent molecules
Molecular Crystals and Liquid Crystals  757(1), 107, 2023
DOI: 10.1080/15421406.2022.2141059
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[2]. Hiroaki Iitsuka, Kun Li, Miyuki Kobayashi, Kikuko Iida, Keiichi Noguchi, Noriyuki Yonezawa, Akiko Okamoto
The crystal structure of (1R *,2S *)-1,2-bis(2-fluorophenyl)-3,8-dimethoxyacenaphthene-1,2-diol, C26H20F2O4
Zeitschrift für Kristallographie - New Crystal Structures  236(6), 1301, 2021
DOI: 10.1515/ncrs-2021-0314
/

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Supporting information


The Supplementary Material for this article can be found online at: Supplementary files

How to cite


Iida, K.; Sakamoto, R.; Li, K.; Kobayashi, M.; Iitsuka, H.; Yonezawa, N.; Okamoto, A. Eur. J. Chem. 2021, 12(2), 147-153. doi:10.5155/eurjchem.12.2.147-153.2114
Iida, K.; Sakamoto, R.; Li, K.; Kobayashi, M.; Iitsuka, H.; Yonezawa, N.; Okamoto, A. Crystal structure of bis(1,8-dibenzoyl-7-methoxynaphthalen-2-yl)terephthalate: Terephthalate phenylene moiety acts as bidentate hydrogen acceptor of bidirectional C-H···π non-classical hydrogen bonds. Eur. J. Chem. 2021, 12(2), 147-153. doi:10.5155/eurjchem.12.2.147-153.2114
Iida, K., Sakamoto, R., Li, K., Kobayashi, M., Iitsuka, H., Yonezawa, N., & Okamoto, A. (2021). Crystal structure of bis(1,8-dibenzoyl-7-methoxynaphthalen-2-yl)terephthalate: Terephthalate phenylene moiety acts as bidentate hydrogen acceptor of bidirectional C-H···π non-classical hydrogen bonds. European Journal of Chemistry, 12(2), 147-153. doi:10.5155/eurjchem.12.2.147-153.2114
Iida, Kikuko, Rei Sakamoto, Kun Li, Miyuki Kobayashi, Hiroaki Iitsuka, Noriyuki Yonezawa, & Akiko Okamoto. "Crystal structure of bis(1,8-dibenzoyl-7-methoxynaphthalen-2-yl)terephthalate: Terephthalate phenylene moiety acts as bidentate hydrogen acceptor of bidirectional C-H···π non-classical hydrogen bonds." European Journal of Chemistry [Online], 12.2 (2021): 147-153. Web. 29 May. 2023
Iida, Kikuko, Sakamoto, Rei, Li, Kun, Kobayashi, Miyuki, Iitsuka, Hiroaki, Yonezawa, Noriyuki, AND Okamoto, Akiko. "Crystal structure of bis(1,8-dibenzoyl-7-methoxynaphthalen-2-yl)terephthalate: Terephthalate phenylene moiety acts as bidentate hydrogen acceptor of bidirectional C-H···π non-classical hydrogen bonds" European Journal of Chemistry [Online], Volume 12 Number 2 (30 June 2021)

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