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.
Authors
- И. А. Колесник (ORCID: https://orcid.org/0000-0003-4921-4299)
- Mohammed Hadi Al–Douh (ORCID: https://orcid.org/0000-0001-9777-2653)
- Atash V. Gurbanov (ORCID: https://orcid.org/0000-0003-1415-8012)
- Елена А. Сорокина (ORCID: https://orcid.org/0000-0001-8867-7988)
- Tuncer Hökelek (ORCID: https://orcid.org/0000-0002-8602-4382)
- Kseniia A. Alekseeva (ORCID: https://orcid.org/0000-0001-6414-7122)
- Mikhail S. Grigoriev (ORCID: https://orcid.org/0000-0002-6363-5535)
- Khudayar I. Hasanov
Institutions
- 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)
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
- Field-Weighted Citation Impact
- 0.00