High-<i>Z</i>′ Crystal Structure of Tricyclic Imidazonaphthyridine Derivatives and the Thermal Profiles of Their Polymorphs
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- Shota Matsumoto
- Faculty of Pharmaceutical Sciences, Showa Pharmaceutical University, 3-3165 Higashi-Tamagawagakuen, Machida, Tokyo 194-8543, Japan
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- Tomohiro Umeno
- Faculty of Pharmaceutical Sciences, Showa Pharmaceutical University, 3-3165 Higashi-Tamagawagakuen, Machida, Tokyo 194-8543, Japan
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- Kazuteru Usui
- Faculty of Pharmaceutical Sciences, Showa Pharmaceutical University, 3-3165 Higashi-Tamagawagakuen, Machida, Tokyo 194-8543, Japan
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- Satoru Karasawa
- Faculty of Pharmaceutical Sciences, Showa Pharmaceutical University, 3-3165 Higashi-Tamagawagakuen, Machida, Tokyo 194-8543, Japan
Description
The crystal structures and thermal profiles of three crystal polymorphs of tricyclic imidazonaphthyridine derivatives ( INA ) were investigated. The aniline derivative INA–AN , in which a 4-anilino moiety was introduced at position 9 of the imidazonaphthyridine framework, yielded a nonplanar curved structure between imidazonaphthyridine and aniline. Three crystals ( INA–AN-α ( I 4 1 / a with Z ′ = 1) as an emissive polymorph, as well as INA–AN-β1 and INA–AN-β2 ( Pc with Z ′ = 4) as nonemissive polymorphs) were obtained. The polymorphs comprised multiple-hydrogen-bond networks. INA–AN-β1 and -β2 crystallized into different polymorphs via recrystallization: INA–AN-β1 and -β2 were obtained from the solvent, as well as via melting and recrystallization processes. Notably, the crystal structures and parameters of INA–AN-β1 and -β2 largely corresponded, although their thermal behaviors were significantly different: INA–AN-β1 underwent a thermal crystal transformation, yielding INA–AN-α at ∼185 °C, while INA–AN-β2 readily melted at ∼190 °C. These distinct profiles indicated that the subtle distinct molecular arrangements, as well as crystal packings, might account for the different thermal profiles of INA–INA-β polymorphs. Interestingly, in addition to INA–AN-β polymorphs, an imidazonaphthyridine framework bearing an N , N -dimethylamine moiety, INA–DMA , crystallized in the P 1̅ space group with Z ′ = 4, indicating that the INA framework containing an aromatic ring afforded high- Z ′ crystal structures.
Journal
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- Crystal Growth & Design
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Crystal Growth & Design 21 (9), 5251-5260, 2021-07-31
American Chemical Society (ACS)
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Details 詳細情報について
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- CRID
- 1360857593734176128
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- ISSN
- 15287505
- 15287483
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- Data Source
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- Crossref
- KAKEN
- OpenAIRE
