A second crystalline modification of 2-{3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}-hydrazinecarbothioamide

Abstract

A second crystalline modification of the title compound, C₁₂H₁₉N₃S [common name: <em>cis</em>-jasmone thiosemicarbazone] was crystallized from tetrahydrofurane at room temperature. There is one crystallographic independent molecule in the asymmetric unit, showing disorder in the <em>cis</em>-jasmone chain [site-occupancy ratio = 0.590 (14):0.410 (14)]. The thiosemicarbazone entity is approximately planar, with the maximum deviation from the mean plane through the N/N/C/S/N atoms being 0.0463 (14) Å [r.m.s.d. = 0.0324 Å], while for the five-membered ring of the jasmone fragment, the maximum deviation from the mean plane through the carbon atoms amounts to 0.0465 (15) Å [r.m.s.d. = 0.0338 Å]. The molecule is not planar due to the dihedral angle between these two fragments, which is 8.93 (1)°, and due to the <em>sp</em>³-hybridized carbon atoms in the jasmone fragment chain. In the crystal, the molecules are connected by N—H&sdot;&sdot;&sdot;S and C—H&sdot;&sdot;&sdot;S interactions, with graph-set motifs <em>R</em>₂²(8) and <em>R</em>₂¹(7), building mono-periodic hydrogen-bonded ribbons along [010]. A Hirshfeld surface analysis indicates that the major contributions for the crystal cohesion are H&sdot;&sdot;&sdot;H (67.8%), H&sdot;&sdot;&sdot;S/S&sdot;&sdot;&sdot;H (15.0%), H&sdot;&sdot;&sdot;C/C&sdot;&sdot;&sdot;H (8.5%) and H&sdot;&sdot;&sdot;N/N&sdot;&sdot;&sdot;H (5.6%) [only non-disordered atoms and those with the highest s.o.f. were considered]. This work reports the second crystalline modification of the <em>cis</em>-jasmone thiosemicarbazone structure, the first one being published recently [Orsoni <em>et al</em>. (2020). <em>Int. J. Mol. Sci.</em> 21, 8681–8697] with the crystals obtained in ethanol at 273 K.