Crystal structure and Hirshfeld surface analysis of a new polymorph of (E)-2-(4-bromophenyl)-1-[2,2-dibromo-1-(3-nitrophenyl)ethenyl]diazene


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Atioglu Z., AKKURT M., Shikhaliyev N. Q., Mammadova N. A., Babayeva G., Khrustalev V. N., ...More

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, vol.78, pp.804-812, 2022 (ESCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 78
  • Publication Date: 2022
  • Doi Number: 10.1107/s2056989022007113
  • Journal Name: ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
  • Journal Indexes: Emerging Sources Citation Index (ESCI), Scopus
  • Page Numbers: pp.804-812
  • Keywords: crystal structure, azo compounds, polymorphism, C-H center dot center dot center dot O interactions, Hirshfeld surface analysis, HYDROGEN-BONDS, HALOGEN
  • Erciyes University Affiliated: Yes

Abstract

A new polymorph of the title compound, C14H8Br3N3O2, (form-2) was obtained in the same manner as the previously reported form-1 [Akkurt et al. (2022). Acta Cryst. E78, 732-736]. The structure of the new polymorph is stabilized by a C-H center dot center dot center dot O hydrogen bond that links molecules into chains. These chains are linked by face-to-face pi-pi stacking interactions, resulting in a layered structure. Short inter-molecular Br center dot center dot center dot O contacts and van der Waals interactions between the layers aid in the cohesion of the crystal packing. In the previously reported form-1, C-H center dot center dot center dot Br interactions connect molecules into zigzag chains, which are linked by C-Br center dot center dot center dot pi interactions into layers, whereas the van der Waals interactions between the layers stabilize the crystal packing of form-2. Hirshfeld molecular surface analysis was used to compare the intermolecular interactions of the polymorphs.