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

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.

Figure 1

The mol­ecular structure of (I). Hydrogen bonds are shown as dashed lines and displacement ellipsoids are drawn at the 50% probability level. [Symmetry codes: (i) −x + 2, −y + 2, −z + 1; (ii) −x + 1, −y + 2, −z; (iii) −x + 2, −y + 2, −z + 2.]

Figure 2

The mol­ecular structure of (II). The hydrogen bond is shown as a dashed line and displacement ellipsoids are drawn at the 50% probability level. [Symmetry code: (i) −x, −y + 1, −z + 1.]

Figure 3

Systematic two-dimensional sheet structure of fumaric acid in (I) viewed along the ac plane. Inter­molecular O—H⋯O hydrogen bonds are shown as dashed lines. One of the two disorder components has been omitted for clarity.

Figure 4

The layered structure of (I) viewed along the a axis. Inter­molecular O—H⋯O and N—H⋯O hydrogen bonds are shown as dashed lines. All hydrogen atoms and one of the two disordered components of the fumaric acid mol­ecules have been omitted for clarity.

Figure 5

Structural unit in the crystal of (II). Inter­molecular O—H⋯N hydrogen bonds are shown as dashed lines.

Figure 6

One-dimensional ribbon structure of (II). Inter­molecular O—H⋯N and C—H⋯O hydrogen bonds are shown as dashed lines. (a) Enlarged view of hydrogen-bonded ring. (b) Overview of the one-dimensional ribbon structure.

Figure 7

The packing of (II). Each blue and green line represents a one-dimensional ribbon structure. All hydrogen atoms have been removed for clarity.