Abstract
The title compound, C12H11N3O2S, was synthesized by a condensation reaction of 2-acetylindan-1,3-dione and thiosemicarbazide in ethanol in the presence of glacial acetic acid. The molecule adopts a thioketone form. The dihedral angle between the mean planes of 1H-inden-1,3(2H)-dione and hydrazinecarbothioamide units is 86.32 (7)°. Weak intramolecular N—H...O and C—H...O hydrogen bonds are observed. In the crystal, molecules are linked via pairs of weak intermolecular N—H...O hydrogen bonds, forming inversion dimers. The dimers are further linked into a three-dimensional network through N—H...S and N—H...O hydrogen bonds, and π–π interactions [centroid–centroid distances = 3.5619 (10)–3.9712 (9) Å].
Highlights
The title compound, C12H11N3O2S, was synthesized by a condensation reaction of 2-acetylindan-1,3-dione and thiosemicarbazide in ethanol in the presence of glacial acetic acid
Molecules are linked via pairs of weak intermolecular N—HÁ Á ÁO hydrogen bonds, forming inversion dimers
The dimers are further linked into a three-dimensional network through N—HÁ Á ÁS and N—HÁ Á ÁO hydrogen bonds, and – interactions [centroid–centroid distances = 3.5619 (10)–3.9712 (9) A ]
Summary
Derivatives obtained from the reaction of 2-acetylindan-1,3-dione and thiosemicarbazide are not widely known in the literature (Sawhney & Lemke, 1983; Kumar et al, 2014). The title compound is completely in a thioketone form and weak intramolecular N— HÁ Á ÁO and C—HÁ Á ÁO hydrogen bonds (N3—HN4Á Á ÁO2 and C12—H12BÁ Á ÁO1; Table 1) are observed (Fig. 1). The length of the C1—S1 bond [1.705 (2) A ] is intermediate between a single bond C—S (1.82 A ) and a double bond C S (1.67 A ) (Allen et al, 1987), which implies that it possesses partial doublebond character indicative of possible delocalization over atoms S1, C1 and N1 This notion is supported by the C1—N1 bond length [1.318 (2) A ], which is shorter than C1—. Two molecules are bound by a pair of N— HÁ Á ÁO hydrogen bonds (N3—HN4Á Á ÁO2iv; Table 1), forming a centrosymmetric dimeric structure (Fig. 2). The centroid–centroid distances are 3.8487 (10), 3.6271 (11), 3.5619 (10), 3.8614 (11) and 3.9712 (9) A , respectively, for Cg1Á Á ÁCg1v, Cg1Á Á ÁCg2vi,
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