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
/


[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
/


References


[1]. Desiraju, G. R. Acc. Chem. Res. 1991, 24 (10), 290-296.
https://doi.org/10.1021/ar00010a002

[2]. Desiraju, G. R. Acc. Chem. Res. 1996, 29 (9), 441-449.
https://doi.org/10.1021/ar950135n

[3]. Steiner, T. Chem. Commun. (Camb.) 1997, No. 8, 727-734.
https://doi.org/10.1039/a603049a

[4]. Dang, L.-L.; Feng, H.-J.; Lin, Y.-J.; Jin, G.-X. J. Am. Chem. Soc. 2020, 142 (44), 18946-18954.
https://doi.org/10.1021/jacs.0c09162

[5]. Gao, Y.; Yin, Q.; Wang, Q.; Li, Z.; Cai, J.; Zhao, T.; Lei, H.; Wang, S.; Zhang, Y.; Shen, B. Adv. Mater. 2020, 32 (48), e2005228.
https://doi.org/10.1002/adma.202005228

[6]. Desiraju, G. R. J. Mol. Struct. 2003, 656 (1-3), 5-15.
https://doi.org/10.1016/S0022-2860(03)00354-5

[7]. Desiraju, G. R. Cryst. Growth Des. 2011, 11 (4), 896-898.
https://doi.org/10.1021/cg200100m

[8]. Aakeröy, C. B.; Seddon, K. R. Chem. Soc. Rev. 1993, 22 (6), 397-407.
https://doi.org/10.1039/CS9932200397

[9]. Desiraju, G. R. C. E. The Design of Organic Solids; Elsevier: Amsterdam, 1989.

[10]. Desiraju, G. R. Angew. Chem. Int. Ed. Engl. 1995, 34 (21), 2311-2327.
https://doi.org/10.1002/anie.199523111

[11]. Hisaki, I.; Nakagawa, S.; Ikenaka, N.; Imamura, Y.; Katouda, M.; Tashiro, M.; Tsuchida, H.; Ogoshi, T.; Sato, H.; Tohnai, N.; Miyata, M. J. Am. Chem. Soc. 2016, 138 (20), 6617-6628.
https://doi.org/10.1021/jacs.6b02968

[12]. Sasaki, T.; Ida, Y.; Hisaki, I.; Tsuzuki, S.; Tohnai, N.; Coquerel, G.; Sato, H.; Miyata, M. Cryst. Growth Des. 2016, 16 (3), 1626-1635.
https://doi.org/10.1021/acs.cgd.5b01724

[13]. Budiman, Y. P.; Jayaraman, A.; Friedrich, A.; Kerner, F.; Radius, U.; Marder, T. B. J. Am. Chem. Soc. 2020, 142 (13), 6036-6050.
https://doi.org/10.1021/jacs.9b11871

[14]. Bondue, C. J.; Koper, M. T. M. J. Am. Chem. Soc. 2019, 141 (30), 12071-12078.
https://doi.org/10.1021/jacs.9b05397

[15]. Elsberg, J. G. D.; Anderson, S. N.; Tierney, D. L.; Reinheimer, E. W.; Berreau, L. M. Dalton Trans. 2021, 50 (5), 1712-1720.
https://doi.org/10.1039/D0DT04074F

[16]. Wozniak, D. I.; Hicks, A. J.; Sabbers, W. A.; Dobereiner, G. E. Dalton Trans. 2019, 48 (37), 14138-14155.
https://doi.org/10.1039/C9DT03511G

[17]. Kang, C.; Zhang, Z.; Wee, V.; Usadi, A. K.; Calabro, D. C.; Baugh, L. S.; Wang, S.; Wang, Y.; Zhao, D. J. Am. Chem. Soc. 2020, 142 (30), 12995-13002.
https://doi.org/10.1021/jacs.0c03691

[18]. Dionne, E. R.; Dip, C.; Toader, V.; Badia, A. J. Am. Chem. Soc. 2018, 140 (32), 10063-10066.
https://doi.org/10.1021/jacs.8b04054

[19]. Tian, X.; Xin, X.; Gao, Y.; Han, Z. CrystEngComm 2018, 20 (11), 1588-1596.
https://doi.org/10.1039/C8CE00026C

[20]. Gargallo, R.; Aviñó, A.; Eritja, R.; Jarosova, P.; Mazzini, S.; Scaglioni, L.; Taborsky, P. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2021, 248 (119185), 119185.
https://doi.org/10.1016/j.saa.2020.119185

[21]. Gomez-Jeria, J. S.; Robles-Navarro, A.; Kpotin, G. A.; Garro-Saez, N.; Gatica-Diaz, N. Chem. Res. J. 2020, 5 (2), 32-52. https://chemrj.org/download/vol-5-iss-2-2020/chemrj-2020-05-02-32-52.pdf (accessed Apr 17, 2021).

[22]. Hahn, R.; Bohle, F.; Fang, W.; Walther, A.; Grimme, S.; Esser, B. J. Am. Chem. Soc. 2018, 140 (51), 17932-17944.
https://doi.org/10.1021/jacs.8b08823

[23]. Zuniga, M. A.; Alderete, J. B.; Jaña, G. A.; Jiménez, V. A. J. Comput. Aided Mol. Des. 2017, 31 (7), 643-652.
https://doi.org/10.1007/s10822-017-0029-2

[24]. Avdeeva, V. V.; Vologzhanina, A. V.; Ugolkova, E. A.; Minin, V. V.; Malinina, E. A.; Kuznetsov, N. T. J. Solid State Chem. 2021, 296 (121989), 121989.
https://doi.org/10.1016/j.jssc.2021.121989

[25]. Kikkawa, S.; Okayasu, M.; Hikawa, H.; Azumaya, I. Cryst. Growth Des. 2021, 21 (2), 1148-1158.
https://doi.org/10.1021/acs.cgd.0c01469

[26]. Kataeva, O.; Nohr, M.; Ivshin, K.; Hampel, S.; Büchner, B.; Knupfer, M. Cryst. Growth Des. 2021, 21 (1), 471-481.
https://doi.org/10.1021/acs.cgd.0c01287

[27]. Awwadi, F. F.; Taher, D.; Kailani, M. H.; Alwahsh, M. I.; Odeh, F.; Rüffer, T.; Schaarschmidt, D.; Lang, H. Cryst. Growth Des. 2020, 20 (2), 543-551.
https://doi.org/10.1021/acs.cgd.9b00408

[28]. Zeng, C.-H.; Wu, H.; Luo, Z.; Yao, J. CrystEngComm 2018, 20 (8), 1123-1129.
https://doi.org/10.1039/C7CE02098H

[29]. Steiner, T.; Desiraju, G. R. Chem. Commun. (Camb.) 1998, No. 8, 891-892.
https://doi.org/10.1039/a708099i

[30]. Desiraju, G. R. Chem. Commun. (Camb.) 2005, No. 24, 2995-3001.
https://doi.org/10.1039/b504372g

[31]. Okamoto, A.; Yonezawa, N. J. Synth. Org. Chem. Japan 2015, 73 (4), 339-360.
https://doi.org/10.5059/yukigoseikyokaishi.73.339

[32]. Okamoto, A.; Yonezawa, N. Chem. Lett. 2009, 38 (9), 914-915.
https://doi.org/10.1246/cl.2009.914

[33]. Okamoto, A.; Mitsui, R.; Oike, H.; Yonezawa, N. Chem. Lett. 2011, 40 (11), 1283-1284.
https://doi.org/10.1246/cl.2011.1283

[34]. Okamoto, A.; Mitsui, R.; Watanabe, S.; Tsubouchi, T.; Yonezawa, N. Int. J. Org. Chem. (Irvine) 2012, 02 (03), 194-201.
https://doi.org/10.4236/ijoc.2012.23029

[35]. Ogata, K.; Mido, T.; Siqingaowa; Noguchi, K.; Yonezawa, N.; Okamoto, A. Chem. Lett. 2019, 48 (12), 1522-1525.
https://doi.org/10.1246/cl.190663

[36]. Mido, T.; Iitsuka, H.; Kobayashi, M.; Noguchi, K.; Yonezawa, N.; Okamoto, A. Chem. Lett. 2020, 49 (3), 295-298.
https://doi.org/10.1246/cl.190903

[37]. Nakaema, K.; Watanabe, S.; Okamoto, A.; Noguchi, K.; Yonezawa, N. Acta Crystallogr. Sect. E Struct. Rep. Online 2008, 64 (Pt 5), o807.
https://doi.org/10.1107/S1600536808007009

[38]. Armarego, W. L. F.; Perrin, D. D. Purification of Laboratory Chemicals, Fourth Edition; Reed Educational and Professional Publishing Ltd: Oxford, 1996.

[39]. Domasevitch, K. V.; Solntsev, P. V.; Krautscheid, H.; Zhylenko, I. S.; Rusanov, E. B.; Chernega, A. N. Chem. Commun. (Camb.) 2012, 48 (47), 5847-5849.
https://doi.org/10.1039/c2cc31770b

[40]. Kato, Y.; Nagasawa, A.; Hijikata, D.; Okamoto, A.; Yonezawa, N. Acta Crystallogr. Sect. E Struct. Rep. Online 2010, 66 (10), o2659-o2659.
https://doi.org/10.1107/S1600536810038195

[41]. Nagasawa, A.; Mitsui, R.; Kato, Y.; Okamoto, A.; Yonezawa, N. Acta Crystallogr. Sect. E Struct. Rep. Online 2010, 66 (10), o2677-o2677.
https://doi.org/10.1107/S1600536810038547

[42]. Rigaku. PROCESS‐AUTO. Rigaku Corporation, Tokyo, Japan, 1998.

[43]. Rigaku. CrystalStructure. Rigaku Corporation, Tokyo, Japan, 2010.

[44]. Burla, M. C.; Caliandro, R.; Camalli, M.; Carrozzini, B.; Cascarano, G. L.; De Caro, L.; Giacovazzo, C.; Polidori, G.; Siliqi, D.; Spagna, R. J. Appl. Crystallogr. 2007, 40 (3), 609-613.
https://doi.org/10.1107/S0021889807010941

[45]. Sheldrick, G. M. Acta Crystallogr. C Struct. Chem. 2015, 71 (1), 3-8.
https://doi.org/10.1107/S2053229614024218


Supporting information


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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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