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

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ABSTRACT

In the title compound, C16H10Cl2N2O2S, the dihedral angles formed by the chloro-substituted benzene rings with the central oxa­diazole ring are 6.54 (9) and 6.94 (8)°. In the crystal, C—H⋯N hydrogen bonding links the mol­ecules into undulating ribbons running parallel to the b axis. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are the H⋯C (18%), H⋯H (17%), H⋯Cl (16.6%), H⋯O (10.4%), H⋯N (8.9%) and H⋯S (5.9%) inter­actions.

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Partial crystal packing of the title compound showing the formation of a undulating ribbon parallel to the b axis through C—H⋯N hydrogen bonds (dashed lines).
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fig2: Partial crystal packing of the title compound showing the formation of a undulating ribbon parallel to the b axis through C—H⋯N hydrogen bonds (dashed lines).

Mentions: In the crystal, mol­ecules are connected by C—H⋯N hydrogen inter­actions, forming undulating ribbons parallel to the b axis (Table 1 ▸, Fig. 2 ▸). The importance of these inter­actions in stabilizing the crystal structure may be determined by comparison with those found in similar related compounds. For instance, in the crystal structure of 2-{5-[(1H-1,2,4-triazol-1-yl)meth­yl]-1,3,4-oxa­diazol-2-yl­thio}-1-(2,4-di­chloro­phen­yl)ethanone (Xu et al., 2005 ▸) mol­ecules are linked into chains via C—H⋯N hydrogen bonds having H⋯N separations of 2.48 Å. and C—H⋯C inter­actions having H⋯N distances of 2.41 Å. Similarly, in the crystal structure of 1,3-bis{[5-(pyridin-2-yl)-1,3,4-oxa­diazol-2-yl]sulfan­yl}propan-2-one (Xia et al., 2011 ▸), two oxa­diazole rings are present and form inter­molecular hydrogen bonds of the type C—H⋯N with distances of 2.51 and 2.54 Å, respectively. Moreover, in the structure of the latter compound, further stabilization of the crystal structure is provided by π–π inter­actions involving the pyridyl and oxa­diazole rings with centroid-to-centroid distances of 3.883 Å.


Crystal structure and Hirshfeld surface analysis of 1-(4-chloro ­ phen ­ yl)-2-{[5-(4-chloro ­ phen ­ yl)-1,3,4-oxa ­ diazol-2-yl]sulfan ­ yl}ethanone
Partial crystal packing of the title compound showing the formation of a undulating ribbon parallel to the b axis through C—H⋯N hydrogen bonds (dashed lines).
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC5382613&req=5

fig2: Partial crystal packing of the title compound showing the formation of a undulating ribbon parallel to the b axis through C—H⋯N hydrogen bonds (dashed lines).
Mentions: In the crystal, mol­ecules are connected by C—H⋯N hydrogen inter­actions, forming undulating ribbons parallel to the b axis (Table 1 ▸, Fig. 2 ▸). The importance of these inter­actions in stabilizing the crystal structure may be determined by comparison with those found in similar related compounds. For instance, in the crystal structure of 2-{5-[(1H-1,2,4-triazol-1-yl)meth­yl]-1,3,4-oxa­diazol-2-yl­thio}-1-(2,4-di­chloro­phen­yl)ethanone (Xu et al., 2005 ▸) mol­ecules are linked into chains via C—H⋯N hydrogen bonds having H⋯N separations of 2.48 Å. and C—H⋯C inter­actions having H⋯N distances of 2.41 Å. Similarly, in the crystal structure of 1,3-bis{[5-(pyridin-2-yl)-1,3,4-oxa­diazol-2-yl]sulfan­yl}propan-2-one (Xia et al., 2011 ▸), two oxa­diazole rings are present and form inter­molecular hydrogen bonds of the type C—H⋯N with distances of 2.51 and 2.54 Å, respectively. Moreover, in the structure of the latter compound, further stabilization of the crystal structure is provided by π–π inter­actions involving the pyridyl and oxa­diazole rings with centroid-to-centroid distances of 3.883 Å.

View Article: PubMed Central - HTML - PubMed

ABSTRACT

In the title compound, C16H10Cl2N2O2S, the dihedral angles formed by the chloro-substituted benzene rings with the central oxa­diazole ring are 6.54 (9) and 6.94 (8)°. In the crystal, C—H⋯N hydrogen bonding links the mol­ecules into undulating ribbons running parallel to the b axis. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are the H⋯C (18%), H⋯H (17%), H⋯Cl (16.6%), H⋯O (10.4%), H⋯N (8.9%) and H⋯S (5.9%) inter­actions.

No MeSH data available.


Related in: MedlinePlus