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Crystal structure and Hirshfeld surface analysis of 1-(4-bromo ­ phen ­ yl)-2-{[5-(pyridin-3-yl)-1,3,4-oxa ­ diazol-2-yl]sulfan ­ yl}ethan-1-one

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ABSTRACT

In the title compound, C15H10BrN3O2S, the dihedral angles between the 1,3,4-oxa­diazole ring and the 3-pyridinyl and bromo­benzene rings are 12.17 (15) and 18.74 (15)°, respectively. In the crystal, the mol­ecules are linked into [100] chains by way of C—H⋯O, C—H⋯N, C—H⋯S hydrogen bonds. The Hirshfeld surface analysis indicates that the most important contributions to the packing are H⋯H (19.5%), N⋯H (17.3%), C⋯H (15.5%), Br⋯H (11.7%), and O⋯H (11.0%) inter­actions.

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The crystal packing of the title compound (I). Only hydrogen atoms involved in hydrogen bonding (dashed lines) are shown.
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fig2: The crystal packing of the title compound (I). Only hydrogen atoms involved in hydrogen bonding (dashed lines) are shown.

Mentions: The packing of (I) is consolidated by C1—H1B⋯O1, C1—H2B⋯S2 and C4—H4A⋯N2 hydrogen bonds, which form chains running along a-axis direction (Fig. 2 ▸, Table 1 ▸). The Hirshfeld surface analysis (Hirshfeld, 1977 ▸) of the crystal structure indicates that the contribution of the H⋯H inter­molecular inter­actions to the crystal packing amounts to 19.5%, N⋯H = 17.3%, Br⋯H = 11.7% and O⋯H = 11.0%. Minor inter­molecular contacts for the cohesion of the structure are: C⋯O = 4.7%, C⋯C = 3.6% and others (Br⋯C, C⋯S, C⋯N, Br⋯S, N⋯N, Br⋯N, O⋯N)= 10.4%. These contacts are represented by conventional mapping of dnorm on the mol­ecular Hirshfeld surface, as shown in Fig. 3 ▸. The H⋯H contribution to the crystal packing is shown as a Hirshfeld surface two-dimensional fingerprint plot with red dots (Wolff et al., 2012 ▸). The de (y axis) and di (x axis) values are the closest external and inter­nal distances (Å) from given points on the Hirshfeld surface (Fig. 4 ▸).


Crystal structure and Hirshfeld surface analysis of 1-(4-bromo ­ phen ­ yl)-2-{[5-(pyridin-3-yl)-1,3,4-oxa ­ diazol-2-yl]sulfan ­ yl}ethan-1-one
The crystal packing of the title compound (I). Only hydrogen atoms involved in hydrogen bonding (dashed lines) are shown.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC5382636&req=5

fig2: The crystal packing of the title compound (I). Only hydrogen atoms involved in hydrogen bonding (dashed lines) are shown.
Mentions: The packing of (I) is consolidated by C1—H1B⋯O1, C1—H2B⋯S2 and C4—H4A⋯N2 hydrogen bonds, which form chains running along a-axis direction (Fig. 2 ▸, Table 1 ▸). The Hirshfeld surface analysis (Hirshfeld, 1977 ▸) of the crystal structure indicates that the contribution of the H⋯H inter­molecular inter­actions to the crystal packing amounts to 19.5%, N⋯H = 17.3%, Br⋯H = 11.7% and O⋯H = 11.0%. Minor inter­molecular contacts for the cohesion of the structure are: C⋯O = 4.7%, C⋯C = 3.6% and others (Br⋯C, C⋯S, C⋯N, Br⋯S, N⋯N, Br⋯N, O⋯N)= 10.4%. These contacts are represented by conventional mapping of dnorm on the mol­ecular Hirshfeld surface, as shown in Fig. 3 ▸. The H⋯H contribution to the crystal packing is shown as a Hirshfeld surface two-dimensional fingerprint plot with red dots (Wolff et al., 2012 ▸). The de (y axis) and di (x axis) values are the closest external and inter­nal distances (Å) from given points on the Hirshfeld surface (Fig. 4 ▸).

View Article: PubMed Central - HTML - PubMed

ABSTRACT

In the title compound, C15H10BrN3O2S, the dihedral angles between the 1,3,4-oxa­diazole ring and the 3-pyridinyl and bromo­benzene rings are 12.17 (15) and 18.74 (15)°, respectively. In the crystal, the mol­ecules are linked into [100] chains by way of C—H⋯O, C—H⋯N, C—H⋯S hydrogen bonds. The Hirshfeld surface analysis indicates that the most important contributions to the packing are H⋯H (19.5%), N⋯H (17.3%), C⋯H (15.5%), Br⋯H (11.7%), and O⋯H (11.0%) inter­actions.

No MeSH data available.