European Journal of Chemistry

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



Main Article Content

Akiko Okamoto
Toyokazu Muto
Siqin Gaowa
Genta Takahara
Noriyuki Yonezawa

Abstract

Crystal structure of 1-(4-hydroxybenzoyl)-2,7-dimethoxynaphthalene, C19O4H16, is reported from the viewpoint of characteristics in the helical alignments and difference compared to the crystal structure of a structural isomeric compound. The asymmetric unit of title compound contains two conformers A and B. Furthermore, the molecules in crystal exhibit atropisomerism brought about by molecular stereogenic axis of carbon-carbon bond between the carbonyl moiety and the naphthalene ring. Therefore, a pair of R- and S-enantiomeric molecules exists for each conformer. The two pairs of the enantiomeric molecules are related by two-fold helical axis in the asymmetric unit of P21/c space group, exhibiting the number of molecules is eight, Z = 8. Single molecular structure of title compound shows non-coplanarly accumulated aromatic-rings structure. The molecular packing structure is mainly stabilized non-classical hydrogen bonds involving C-H…O hydrogen bonds and C-H…π ones, however O-H…O=C classical hydrogen bonds are solely formed between same configured conformers. Comparison with the spatial alignment of an isomeric homologue, 2-hydroxy-1-(4-methoxy benzoyl)-7-methoxynaphthalene, has clarified that substitution position of hydroxy group determines not only direction of classical hydrogen bonds but also total feature of molecular packing, i.e., the homologous compound, which has hydroxy group at 2-position of naphthalene core forms intramolecular O-H…O=C classical hydrogen bond, and O-H…OMe classical hydrogen bonds between opposite enantiomeric isomers. The presence/absence and direction of the predominantly strong classical hydrogen bonds govern balance of interactions of other less effective classical and non-classical hydrogen bonds in molecular packing. In homologous compound, each of non-classical hydrogen bonds between same signed enantiomeric isomers and those between opposite enantiomeric isomers demonstrates almost same distances. In title compound, both types of non-classical hydrogen bonds formed by conformer A are imbalanced. The imbalanced non-classical hydrogen bonds are adjusted and reinforced by non-classical hydrogen bonds between conformers A and B.


icon graph This Abstract was viewed 1556 times | icon graph Article PDF downloaded 577 times icon graph Article CIF FILE downloaded 0 times

How to Cite
(1)
Okamoto, A.; Muto, T.; Gaowa, S.; Takahara, G.; Yonezawa, N. Crystal Structure of 1-(4-Hydroxybenzoyl)-2,7-Dimethoxynaphthalene: Contribution of Classical and Non-Classical Hydrogen Bonding Interactions to the Molecular Packing Structure. Eur. J. Chem. 2017, 8, 33-41.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. Veguillas, M.; Sola, R.; Fernandez-Ibanez, M. A.; Macia, B. Tetrahedron: Asymmetry 2016, 27(14-15), 643-648.
https://doi.org/10.1016/j.tetasy.2016.06.001

[2]. Kamachi, T.; Yoshizawa, K. Org. Lett. 2014, 16(2), 472-475.
https://doi.org/10.1021/ol4033545

[3]. Goel, A.; Kumar, V.; Hemberger, Y.; Singh, F.; Nag, P.; Knauer, M.; Kant, R.; Raghunandan, R.; Maulik, P. R.; Bringman, G. J. Org. Chem. 2016, 81(22), 10721-10732.
https://doi.org/10.1021/acs.joc.6b01804

[4]. Fer, M. J.; Cinqualbre, J.; Bortoluzzi, J.; Chesse, M.; Leroux, F. R.; Panossian, A. Eur. J. Org. Chem. 2016, 2016(26), 4545-4553.
https://doi.org/10.1002/ejoc.201600727

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

[6]. Okamoto, A.; Mitsui, R.; Yonezawa, N. Chem. Lett. 2011, 40, 1283-1284.
https://doi.org/10.1246/cl.2011.1283

[7]. Tsumuki, T.; Hijikata, D.; Okamoto, A.; Oike, H.; Yonezawa, N. Acta Cryst. 2011, E67, o2095-o2095.

[8]. Narushima, S.; Mohri, S.; Yonezawa, N.; Okamoto, A. Acta Cryst. 2014, E70, 170-173.

[9]. Mohri, S.; Ohisa, S.; Isozaki, K.; Yonezawa, N.; Okamoto, A. Acta Cryst. 2015, C71, 344-350.

[10]. Hijikata, D.; Takada, T.; Nagasawa, A.; Okamoto, A.; Yonezawa, N. Acta Cryst. 2010, E66, o2902-o2903.

[11]. Yoshiwaka, S.; Sasagawa, K.; Noguchi, K.; Yonezawa, N.; Okamoto, A. Acta Cryst. 2014, C70, 1096-1100.

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

[13]. Okamoto, A.; Watanabe, S.; Nakaema, K.; Yonezawa, N. Cryst. Str. Theo. Appl. 2012, 1, 121-127.

[14]. Okamoto, A.; Nagasawa, A.; Yonezawa, N. Eur. Chem. Bull. 2014, 3(1), 13-17.

[15]. Armarego, W. L. F.; Chai, C. L. L. Purification of Laboratory Chemicals, Seventh edition, 2013, Elsevier Inc., Oxford, UK.

[16]. Watanabe, S.; Muto, T.; Nagasawa, A.; Okamoto, A.; Yonezawa, N. Acta Cryst. 2011, E67, o1466-o1466.

[17]. Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.

[18]. Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.

[19]. 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. Cryst. 2007, 40, 609-613.
https://doi.org/10.1107/S0021889807010941

[20]. Sheldrick, G. M. Acta Cryst. 2008, A64, 112-122.
https://doi.org/10.1107/S0108767307043930

[21]. Burnett, M. N.; Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.

[22]. Hisaki, I.; Sasaki, T.; Tohnai, N.; Miyata, M. Chem. Eur. J. 2012, 18(33), 10066-10073.
https://doi.org/10.1002/chem.201200688

[23]. Tanaka, A.; Hisaki, I.; Tohnai, N.; Miyata, M. Chem. Asian J. 2007, 2, 230-238.
https://doi.org/10.1002/asia.200600332

[24]. Hisaki, I.; Tohnai, N.; Miyata, M. Chirality 2008, 20, 330-336.
https://doi.org/10.1002/chir.20443

[25]. Yuge, T.; Sakai, T.; Kai, N.; Hisaki, I.; Miyata, M.; Tohnai, N. Chem. Eur. J. 2008, 14, 2984-2993.
https://doi.org/10.1002/chem.200701709

Supporting Agencies

Prof. Keiichi Noguchi, Instrumentation Analysis Center, Tokyo University of Agriculture and Technology, the Ogasawara Foundation for the Promotion of Science & Engineering, Tokyo, Japan.
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).