Synthesis, crystal structure, Hirshfeld surface and crystal void analysis of 4-fluoro-benzo[ c][1,2,5]selena-diazol-1-ium chloride

Atash V Gurbanov; Tuncer Hökelek; Gunay Z Mammadova; Khudayar I Hasanov; Tahir A Javadzade; Alebel N Belay

doi:10.1107/S2056989025001379

Synthesis, crystal structure, Hirshfeld surface and crystal void analysis of 4-fluoro-benzo[ c][1,2,5]selena-diazol-1-ium chloride

Acta Crystallogr E Crystallogr Commun. 2025 Feb 20;81(Pt 3):252-256. doi: 10.1107/S2056989025001379. eCollection 2025 Mar 1.

Authors

Atash V Gurbanov¹, Tuncer Hökelek², Gunay Z Mammadova³, Khudayar I Hasanov⁴, Tahir A Javadzade⁵, Alebel N Belay⁶

Affiliations

¹ Excellence Center, Baku State University, Z. Xalilov Str. 23, Az 1148 Baku, Azerbaijan.
² Hacettepe University, Department of Physics, 06800 Beytepe-Ankara, Türkiye.
³ Department of Chemistry, Baku State University, Z. Khalilov Str. 23, Az 1148 Baku, Azerbaijan.
⁴ Azerbaijan Medical University, Scientific Research Centre (SRC), A. Kasumzade Str. 14, AZ 1022 Baku, Azerbaijan.
⁵ Department of Chemistry and Chemical Engineering, Khazar University, Mahzati Str. 41, AZ 1096 Baku, Azerbaijan.
⁶ Department of Chemistry, Bahir Dar University, PO Box 79, Bahir Dar, Ethiopia.

Abstract

The asymmetric unit of the title salt, C₆H₄FN₂Se⁺·Cl^-, contains one planar 4-fluoro-benzo[c][1,2,5]selena-diazol-1-ium mol-ecular cation and a chloride anion. In the crystal, inter-molecular N-H⋯Cl hydrogen bonds link the 4-fluoro-benzo[c][1,2,5]selena-diazol-1-ium mol-ecules, which are arranged in parallel layers along (104), to the chloride anions. The cationic layers, in turn, are stacked along [001]. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯Cl/Cl⋯H (22.6%), H⋯F/F⋯H (13.9%), H⋯N/N⋯H (11.9%), H⋯C/C⋯H (10.2%) and H⋯H (7.7%) inter-actions. The volume of the crystal voids and the percentage of free space were calculated to be 44.80 Å³ and 5.91%, showing that there is no large cavity in the crystal packing.

Keywords: chalcogen bond; crystal structure; non-covalent interactions; organic–inorganic salt.