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Crystal structure and Hirshfeld surface analysis of 4-allyl-6-bromo-2-(4-chlorophenyl)-4H-imidazo[4,5-b]pyridine

Abstract : The title compound, C15H11BrClN3, is built up from a planar imidazo[4,5-b]pyridine unit linked to phenyl and allyl substituents. The allyl substituent is rotated significantly out of the imidazo[4,5-b]pyridine plane, while the benzene ring is inclined by 3.84 (6)° to the ring system. In the crystal, mol­ecules are linked via a pair of weak inter­molecular C—H...N hydrogen bonds, forming an inversion dimer with an R22(20) ring motif. The dimers are further connected by π–π stacking inter­actions between the imidazo[4,5-b]pyridine ring systems [centroid–centroid distances = 3.7161 (13) and 3.8478 (13) Å]. The important contributions to the Hirshfeld surface are H...H (35.9%), H...Cl/Cl...H (15.0%), H...C/C...H (12.4%), H...Br/Br...H (10.8%), H...N/N...H (7.5%), C...Br/Br...C (5.9%), C...C (5.5%) and C...N/N...C (4.0%) contacts.
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https://hal.univ-lille.fr/hal-03038104
Contributeur : Lilloa Université de Lille <>
Soumis le : jeudi 3 décembre 2020 - 12:11:16
Dernière modification le : mercredi 17 février 2021 - 09:56:08

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Selma Bourichi, Youssef Kandri Rodi, Tuncer Hökelek, Amal Haoudi, Catherine Renard, et al.. Crystal structure and Hirshfeld surface analysis of 4-allyl-6-bromo-2-(4-chlorophenyl)-4H-imidazo[4,5-b]pyridine. Acta crystallographica. Section E, Crystallographic communications, International Union of Crystallography, 2019, 75, pp.43-48. ⟨10.1107/S2056989018017322⟩. ⟨hal-03038104⟩

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