Crystal structure and Hirshfeld surface analysis of 4-bromo-6-(4-chlorophenyl)-6,7-dihydro-5 <i>H</i> -furo[2,3- <i>f</i> ]isoindol-5-one

The mol-ecule of the title compound, C<sub>16</sub>H<sub>9</sub>BrClNO<sub>2</sub>, contains furan and phenyl rings and an iso-indole ring system. The phenyl ring subtends a dihedral angle of 10.3 (2)° with the fused ring system. In the crystal, C-H⋯O hydrogen bonds link the mol-ecules into a two-dimensional network nearly parallel to the <i>ab</i> plane, enclosing <i>R</i> <sup>2</sup> <sub>2</sub>(6), <i>R</i> <sup>4</sup> <sub>4</sub>(12), <i>R</i> <sup>4</sup> <sub>4</sub>(14), <i>R</i> <sup>4</sup> <sub>4</sub>(18) and <i>R</i> <sup>4</sup> <sub>4</sub>(20) ring motifs. π-π stacking between the centroids of parallel rings [centroid-centroid distances = 3.919 (3)-3.695 (3) Å] helps to consolidate the packing. Hirshfeld surface analysis revealed that the most important contributions for the crystal packing are from H⋯H (21.2%), H⋯Cl/Cl⋯H (14.7%), H⋯O/O⋯H (13.9%), H⋯C/C⋯H (13.1%), H⋯Br/Br⋯H (12.3%) and C⋯C (11.6%) inter-actions.

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Publication Details

Journal
Acta Crystallographica Section E Crystallographic Communications
Published
2025-10-02
DOI
https://doi.org/10.1107/s2056989025008606
Primary Topic
Synthesis and pharmacology of benzodiazepine derivatives
Type
article
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article

Crystal structure and Hirshfeld surface analysis of 4-bromo-6-(4-chlorophenyl)-6,7-dihydro-5 H -furo[2,3- f ]isoindol-5-one

И. А. Колесник, Mohammed Hadi Al–Douh, Atash V. Gurbanov, Елена А. Сорокина et al.
Acta Crystallographica Section E Crystallographic Communications
Synthesis and pharmacology of benzodiazepine derivatives
article

Crystal structure and Hirshfeld surface analysis of 4-bromo-6-(4-chlorophenyl)-6,7-dihydro-5 H -furo[2,3- f ]isoindol-5-one

И. А. Колесник, Mohammed Hadi Al–Douh, Atash V. Gurbanov, Елена А. Сорокина, Tuncer Hökelek, Kseniia A. Alekseeva, Mikhail S. Grigoriev, Khudayar I. Hasanov
article en

Abstract

The mol-ecule of the title compound, C<sub>16</sub>H<sub>9</sub>BrClNO<sub>2</sub>, contains furan and phenyl rings and an iso-indole ring system. The phenyl ring subtends a dihedral angle of 10.3 (2)° with the fused ring system. In the crystal, C-H⋯O hydrogen bonds link the mol-ecules into a two-dimensional network nearly parallel to the <i>ab</i> plane, enclosing <i>R</i> <sup>2</sup> <sub>2</sub>(6), <i>R</i> <sup>4</sup> <sub>4</sub>(12), <i>R</i> <sup>4</sup> <sub>4</sub>(14), <i>R</i> <sup>4</sup> <sub>4</sub>(18) and <i>R</i> <sup>4</sup> <sub>4</sub>(20) ring motifs. π-π stacking between the centroids of parallel rings [centroid-centroid distances = 3.919 (3)-3.695 (3) Å] helps to consolidate the packing. Hirshfeld surface analysis revealed that the most important contributions for the crystal packing are from H⋯H (21.2%), H⋯Cl/Cl⋯H (14.7%), H⋯O/O⋯H (13.9%), H⋯C/C⋯H (13.1%), H⋯Br/Br⋯H (12.3%) and C⋯C (11.6%) inter-actions.

Acta Crystallographica Section E Crystallographic CommunicationsVol. 81(11)
Peoples' Friendship University of Russia (RU), National Academy of Sciences of Belarus (BY), Azerbaijan Medical University (AZ), Baku State University (AZ), Russian New University (RU), Hadhramout University (YE), Frumkin Institute of Physical Chemistry and Electrochemistry Russian Academy of Sciences (RU), Hacettepe University (TR)
Openalex Percentile: Top 79%
Synthesis and pharmacology of benzodiazepine derivatives
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