Crystal structure of a 1:1 co-crystal of quabodepistat (OPC-167832) with 2,5-dihydroxybenzoic acid using microcrystal electron diffraction
Quabodepistat [(5-{[(3R,4R)-1-(4-chloro-2,6-difluorophenyl)-3,4-dihydroxypiperidin-4-yl]methoxy}-8-fluoro-3,4-dihydroquinolin-2(1H)-one); C21H20ClF3N2O4] and 2,5-dihydroxybenzoic acid (2,5DHBA; C7H6O4) were successfully co-crystallized. Given the small size of the crystals (1 × 0.2 × 0.2 µm) the str...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2023-10-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989023006047 |
| _version_ | 1827774562214871040 |
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| author | Nasa Sakamoto Katsuhiko Gato |
| author_facet | Nasa Sakamoto Katsuhiko Gato |
| author_sort | Nasa Sakamoto |
| collection | DOAJ |
| description | Quabodepistat [(5-{[(3R,4R)-1-(4-chloro-2,6-difluorophenyl)-3,4-dihydroxypiperidin-4-yl]methoxy}-8-fluoro-3,4-dihydroquinolin-2(1H)-one); C21H20ClF3N2O4] and 2,5-dihydroxybenzoic acid (2,5DHBA; C7H6O4) were successfully co-crystallized. Given the small size of the crystals (1 × 0.2 × 0.2 µm) the structure was solved via microcrystal electron diffraction (MicroED). The C—O and C=O bond-length ratio of the carboxylic group in 2,5DHBA is 1.08 (1.34 Å/1.24 Å), suggesting that 2,5DHBA remains protonated. Therefore, the material is a co-crystal rather than a salt. The amide group of quabodepistat participates in a cyclic hydrogen bond with the carboxylic group of the 2,5DHBA. Additional hydrogen bonds involving the quabodepistat amide and hydroxyl groups result in a three-dimensional network. |
| first_indexed | 2024-03-11T13:40:07Z |
| format | Article |
| id | doaj.art-3048a425765a46c5b8a25ee11de7ba09 |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-03-11T13:40:07Z |
| publishDate | 2023-10-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-3048a425765a46c5b8a25ee11de7ba092023-11-02T13:44:32ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902023-10-01791092092210.1107/S2056989023006047dj2052Crystal structure of a 1:1 co-crystal of quabodepistat (OPC-167832) with 2,5-dihydroxybenzoic acid using microcrystal electron diffractionNasa Sakamoto0Katsuhiko Gato1Preformulation Research Laboratory, CMC Headquarters, Otsuka Pharmaceutical Co., Ltd., Tokushima, 771-0182, JapanPreformulation Research Laboratory, CMC Headquarters, Otsuka Pharmaceutical Co., Ltd., Tokushima, 771-0182, JapanQuabodepistat [(5-{[(3R,4R)-1-(4-chloro-2,6-difluorophenyl)-3,4-dihydroxypiperidin-4-yl]methoxy}-8-fluoro-3,4-dihydroquinolin-2(1H)-one); C21H20ClF3N2O4] and 2,5-dihydroxybenzoic acid (2,5DHBA; C7H6O4) were successfully co-crystallized. Given the small size of the crystals (1 × 0.2 × 0.2 µm) the structure was solved via microcrystal electron diffraction (MicroED). The C—O and C=O bond-length ratio of the carboxylic group in 2,5DHBA is 1.08 (1.34 Å/1.24 Å), suggesting that 2,5DHBA remains protonated. Therefore, the material is a co-crystal rather than a salt. The amide group of quabodepistat participates in a cyclic hydrogen bond with the carboxylic group of the 2,5DHBA. Additional hydrogen bonds involving the quabodepistat amide and hydroxyl groups result in a three-dimensional network.http://scripts.iucr.org/cgi-bin/paper?S2056989023006047crystal structureco-crystalquabodepistat2,5-dihydroxybenzoic acidmicrocrystal electron diffraction |
| spellingShingle | Nasa Sakamoto Katsuhiko Gato Crystal structure of a 1:1 co-crystal of quabodepistat (OPC-167832) with 2,5-dihydroxybenzoic acid using microcrystal electron diffraction Acta Crystallographica Section E: Crystallographic Communications crystal structure co-crystal quabodepistat 2,5-dihydroxybenzoic acid microcrystal electron diffraction |
| title | Crystal structure of a 1:1 co-crystal of quabodepistat (OPC-167832) with 2,5-dihydroxybenzoic acid using microcrystal electron diffraction |
| title_full | Crystal structure of a 1:1 co-crystal of quabodepistat (OPC-167832) with 2,5-dihydroxybenzoic acid using microcrystal electron diffraction |
| title_fullStr | Crystal structure of a 1:1 co-crystal of quabodepistat (OPC-167832) with 2,5-dihydroxybenzoic acid using microcrystal electron diffraction |
| title_full_unstemmed | Crystal structure of a 1:1 co-crystal of quabodepistat (OPC-167832) with 2,5-dihydroxybenzoic acid using microcrystal electron diffraction |
| title_short | Crystal structure of a 1:1 co-crystal of quabodepistat (OPC-167832) with 2,5-dihydroxybenzoic acid using microcrystal electron diffraction |
| title_sort | crystal structure of a 1 1 co crystal of quabodepistat opc 167832 with 2 5 dihydroxybenzoic acid using microcrystal electron diffraction |
| topic | crystal structure co-crystal quabodepistat 2,5-dihydroxybenzoic acid microcrystal electron diffraction |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989023006047 |
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