Crystal structure and Hirshfeld surface analysis of ethyl 2-{4-[(3-methyl-2-oxo-1,2-di-hydro-quinoxalin-1-yl)meth-yl]-1H-1,2,3-triazol-1-yl}acetate.

Nada Kheira Sebbar,Nadeem Abad,Tuncer Hökelek,El Mokhtar Essassi,Youssef Ramli,Joel T Mague

doi:10.1107/s2056989018014561

Nada Kheira Sebbar, Nadeem Abad + Show 4 more

Open Access

https://doi.org/10.1107/s2056989018014561

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Abstract

The mol-ecule of the title compound, C16H17N5O3, is build up from two fused six-membered rings linked to a 1,2,3-triazole ring, which is attached to an ethyl azido-acetate group. The di-hydro-qinoxalinone portion is planar to within 0.0512 (12) Å and is oriented at a dihedral angle of 87.83 (5)° with respect to the pendant triazole ring. In the crystal, a combination of inter-molecular C-H⋯O and C-H⋯N hydrogen bonds together with slipped π-stacking [centroid-centroid distance = 3.7772 (12) Å] and C-H⋯π (ring) inter-actions lead to the formation of chains extending along the c-axis direction. Additional C-H⋯O hydrogen bonds link these chains into layers parallel to the bc plane and the layers are tied together by complementary π-stacking [centroid-centroid distance = 3.5444 (12) Å] inter-actions. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (44.5%), H⋯O/O⋯H (18.8%), H⋯N/N⋯H (17.0%) and H⋯C/C⋯H (10.4%) inter-actions.

Highlights

Nadeem Abad,a* Youssef Ramli,b Tuncer Hokelek,c Nada Kheira Sebbar,d Joel T
The molecule of the title compound, C16H17N5O3, is build up from two fused sixmembered rings linked to a 1,2,3-triazole ring, which is attached to an ethyl azido-acetate group
A combination of intermolecular C—HÁ Á ÁO and C—HÁ Á ÁN hydrogen bonds together with slipped -stacking [centroid– centroid distance = 3.7772 (12) A ] and C—HÁ Á Á interactions lead to the formation of chains extending along the c-axis direction

Summary

Chemical context

Quinoxaline derivatives, especially quinoxalinone, are of great importance in medicinal chemistry (Ramli & Essassi, 2015; Ramli et al, 2017) and can be used for the synthesis of numerous heterocyclic compounds with various biological activities such as antibacterial (Griffith et al, 1992), HIV (Loriga et al, 1997), antimicrobial (Badran et al, 2003), antiinflammatory (Wagle et al, 2008), antiprotozoal (Hui et al, 2006), and anticancer (Carta et al, 2006). In a continuation of our research work devoted to the study of cycloaddition reactions involving quinoxaline derivatives (Ramli et al, 2011, 2013; Abad et al, 2018; Sebbar et al, 2016), we report in this work the synthesis, using 3-methyl-1-(prop-2-ynyl)-3,4-dihydroquinoxalin-2(1H)-one as dipolarophile and ethyl azido acetate as 1,3-dipole, and crystal structure of ethyl 2-{4-[(3methyl-2-oxo-1,2-dihydroquinoxalin-1-yl)methyl]-1H-1,2,3triazol-1-yl}acetate, C16H17N5O3 (Fig. 1)

Structural commentary

Supramolecular features

Synthesis and crystallization

Findings

Refinement