Crystal structures of two different multi-component crystals consisting of 1-(3,4-di-meth-oxy-benz-yl)-6,7-di-meth-oxy-iso-quinoline and fumaric acid

Hiroki Shibata; Aya Sakon; Noriyuki Takata; Hiroshi Takiyama

doi:10.1107/S2056989024009794

Crystal structures of two different multi-component crystals consisting of 1-(3,4-di-meth-oxy-benz-yl)-6,7-di-meth-oxy-iso-quinoline and fumaric acid

Acta Crystallogr E Crystallogr Commun. 2024 Oct 11;80(Pt 11):1146-1150. doi: 10.1107/S2056989024009794. eCollection 2024 Oct 1.

Authors

Hiroki Shibata^{1

2}, Aya Sakon³, Noriyuki Takata⁴, Hiroshi Takiyama²

Affiliations

¹ Pharmaceutical Technology Division, Analytical Development Department, Chugai Pharmaceutical Co. Ltd., 5-5-1 Ukima, Kita-ku, Tokyo 115-8543, Japan.
² Department of Applied Physics and Chemical Engineering Tokyo University of Agriculture and Technology 2-24-16 Naka-cho Koganei Tokyo 184-8588 Japan.
³ Pharmaceutical Technology Division, Formulation Development Department, Chugai Pharmaceutical Co. Ltd., 216 Totsuka-cho, Totsuka-ku, Yokohama, Kanagawa 244-8602, Japan.
⁴ Manufacturing Technology Division, Quality Development Department, Chugai Pharma Manufacturing Co. Ltd., 2500 Takayanagi, Fujieda, Shizuoka 426-0041, Japan.

Abstract

Two different multi-component crystals consisting of papaverine [1-(3,4-di-meth-oxy-benz-yl)-6,7-di-meth-oxy-iso-quinoline, C₂₀H₂₁NO₄] and fumaric acid [C₄H₄O₄] were obtained. Single-crystal X-ray structure analysis revealed that one, C₂₀H₂₁NO₄·1.5C₄H₄O₄ (I), is a salt co-crystal composed of salt-forming and non-salt-forming mol-ecules, and the other, C₂₀H₂₁NO₄·0.5C₄H₄O₄ (II), is a salt-co-crystal inter-mediate (i.e., in an inter-mediate state between a salt and a co-crystal). In this study, one state (crystal structure at 100 K) within the salt-co-crystal continuum is defined as the 'inter-mediate'.

Keywords: crystal structure; fumaric acid; multi-component crystal; papaverine.