Pockets and channels in tennimide solvate structures: Influence of solvent on crystal packing behaviour

Gallagher, John F.; Mocilac, Pavle

doi:10.1016/j.molstruc.2021.130149

Cited by 3 publications

(2 citation statements)

References 32 publications

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“…Examination of the crystal structures of the 17 solvatomorphs shows that the solvents are located in channels (in most cases) or lattice pockets 73 (Fig. 6).…”

Section: Resultsmentioning

confidence: 99%

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Solvatomorphism with polar protic/aprotic and non-polar solvents in a series of complexes derived from the 5-phenylimidazole/tetrafluoroborate/copper(ii) reaction system

Delegkou,

Panagiotou,

Papatriantafyllopoulou

et al. 2024

CrystEngComm

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“…Examination of the crystal structures of the 17 solvatomorphs shows that the solvents are located in channels (in most cases) or lattice pockets 73 (Fig. 6).…”

Section: Resultsmentioning

confidence: 99%

“…As shown in Table 3 and Location and role of the solvents in the crystal structures. Examination of the crystal structures of the 17 solvatomorphs shows that the solvents are located in channels (in most cases) or lattice pockets 73 (Fig. 6).…”

Section: Description Of the Structuresmentioning

confidence: 99%

Solvatomorphism with polar protic/aprotic and non-polar solvents in a series of complexes derived from the 5-phenylimidazole/tetrafluoroborate/copper(ii) reaction system

Delegkou,

Panagiotou,

Papatriantafyllopoulou

et al. 2024

CrystEngComm

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Solvatomorphism in a series of copper(II) complexes with the 5-phenylimidazole/perchlorate system as ligands

Loukopoulos,

Papatriantafyllopoulou,

Moushi

et al. 2024

Acta Crystallogr B Struct Sci Cryst Eng Mater

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In the course of an investigation of the supramolecular behaviour of copper(II) complexes with the 5-phenylimidazole/perchlorate ligand system (`blend') remarkable solvatomorphism has been observed. By employing a variety of crystallization solvents (polar protic, polar/non-polar aprotic), a series of 12 crystalline solvatomorphs with the general formula [Cu(ClO4)2(LH)4]·x(solvent) have been obtained [LH = 5-phenylimidazole, x(solvent) = 3.3(H2O) (1), 2(methanol) (2), 2(ethanol) (3), 2(1-propanol) (4), 2(2-propanol) (5), 2(2-butanol) (6), 2(dimethylformamide) (7), 2(acetone) (8), 2(tetrahydrofurane) (9), 2(1,4-dioxane) (10), 2(ethyl acetate) (11) and 1(diethyl ether) (12)]. The structures have been solved using single-crystal X-ray diffraction and the complexes were characterized by thermal analysis and infrared spectroscopy. The solvatomorphs are isostructural (triclinic, P 1), with the exception of compound 9 (monoclinic, P21/n). The supramolecular structures and the role of the various solvents is discussed. All potential hydrogen-bond functionalities, both of the [Cu(ClO4)2(LH)4] units and of the solvents, are utilized in the course of the crystallization process. The supramolecular assembly in all structures is directed by strong recurring Nimidazole–H...Operchlorate motifs leading to robust scaffolds composed of the [Cu(ClO4)2(LH)4] host complexes. The solvents are located in channels and, with the exception of the disordered waters in 1 and the diethyl ether in 12, participate in hydrogen-bonding formation with the [Cu(ClO4)2(LH)4] complexes, serving as both hydrogen-bond acceptors and donors (for the polar protic solvents in 2–6), or solely as hydrogen-bond acceptors (for the polar/non-polar aprotic solvents in 7–11), linking the complexes and contributing to the stability of the crystalline compounds.

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The unusual (syn-/anti-)₂ conformation of a dimethoxypyrimidyl-based tennimide

Mocilac,

Pohl,

Gallagher

2023

Acta Cryst E

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The tennimide macrocycle, (I) (C52H40N16O16.0.167H2O), was synthesized from 2-amino-4,6-dimethoxypyrimidine and pyridine-2,6-dicarbonyl dichloride. Compound (I) represents the first tennimide incorporating pyridine rings in the macrocycle scaffold. In the macrocycle ring, the carbonyl groups at each successive dicarbonyl(pyridine) moiety adopt the (syn/anti)2 conformation. This contrasts with all previously reported tetraimide macrocycles, which exhibit the (syn)4 conformation. The effect is to close any potential cavity or niche by having two of the central pyridine C5N rings aligned close to each other [with closest pyridine Cg...Cg ring centroid separations of 3.5775 (19) Å; closest C...C = 3.467 (5) Å]. A partial occupancy water molecule (with s.o.f. = 0.167), resides with its oxygen atom on a twofold axis at hydrogen-bonding distances to the carbonyl O atom, in a molecular niche between two pyridine rings. Macrocyles of (I) have all six C=O groups and all eight methoxy O atoms present on the macrocycle surface. However, all twelve N atoms are effectively shielded on steric grounds from any potential intermolecular interactions. The remaining two C=O O atoms interact with the partial occupancy water molecule via two O—H...O=C hydrogen bonds. Macrocycles of (I) stack as one-dimensional chains along the b-axis direction with primary intermolecular interactions involving weak C—H...O=C/OCH3/H2O contacts. Chains interlock weakly via methoxy–methoxy C—H...O interactions into two-dimensional sheets.

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Pockets and channels in tennimide solvate structures: Influence of solvent on crystal packing behaviour

Cited by 3 publications

References 32 publications

Solvatomorphism with polar protic/aprotic and non-polar solvents in a series of complexes derived from the 5-phenylimidazole/tetrafluoroborate/copper(ii) reaction system

Solvatomorphism with polar protic/aprotic and non-polar solvents in a series of complexes derived from the 5-phenylimidazole/tetrafluoroborate/copper(ii) reaction system

Solvatomorphism in a series of copper(II) complexes with the 5-phenylimidazole/perchlorate system as ligands

The unusual (syn-/anti-)₂ conformation of a dimethoxypyrimidyl-based tennimide

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Pockets and channels in tennimide solvate structures: Influence of solvent on crystal packing behaviour

Cited by 3 publications

References 32 publications

Solvatomorphism with polar protic/aprotic and non-polar solvents in a series of complexes derived from the 5-phenylimidazole/tetrafluoroborate/copper(ii) reaction system

Solvatomorphism with polar protic/aprotic and non-polar solvents in a series of complexes derived from the 5-phenylimidazole/tetrafluoroborate/copper(ii) reaction system

Solvatomorphism in a series of copper(II) complexes with the 5-phenylimidazole/perchlorate system as ligands

The unusual (syn-/anti-)2 conformation of a dimethoxypyrimidyl-based tennimide

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The unusual (syn-/anti-)₂ conformation of a dimethoxypyrimidyl-based tennimide