The crystal structure of a biologically active (E)-1-[(2-chloro-1,3-thiazol-5-yl)methyl)]-3-methyl-2-nitroguanidine with molecular formula C6H8N5O2ClS has been investigated based on the molecular conformation and the supramolecular packing in terms of intermolecular interactions involving N–H？O, N–H？N, and C–H？O–N (nitro group), C–H？N (thiazol) hydrogen bonds, offset π–π stacking, C–H？π and N(–NO2)？C=N intermolecular interactions. Furthermore, a short C–Cl？O–N contact is also present which contributes towards the crystal packing. The lattice energy of the title compound has been calculated using the PIXEL approach (the Coulomb-London-Pauli (CLP) model) and compared with periodic calculations performed using CRYSTAL09. In addition, Hirshfeld surface analysis and fingerprint plots provide a platform for the evaluation of the contribution of different intermolecular interactions towards the packing behaviour. 1. Introduction (E)-1-(2-Chloro-1,3-thiazol-5-ylmethyl)-3-methyl-2-nitroguanidine [1] constitutes a new class of neonicotinoid insecticides [2–5], which is useful to rice, leafy vegetables, tomato, and tea to control noxious insects, with excellent systemic action [6]. Clothianidin exhibits excellent control efficacies in small amounts for a wide variety of insect pests such as Hemiptera, Thysanoptera, Coleoptera, Lepidoptera, and Diptera for a long term, with excellent systemic action and by a variety of application methods [7]. The crystal structure of this title compound has been reported in 2003 [8]. It is of interest to investigate the crystal packing of the molecule in the solid state. Furthermore, an investigation of the molecular conformation in the solid state and comparison with the gas phase is also of relevance. In addition, a quantitative estimation of the energetics and nature of weak intermolecular interactions which pack the solid have also been performed. Keeping in mind the above-mentioned viewpoints we have recrystallized the compound and redetermined the crystal structure by single crystal X-ray diffraction at 100(2)K. The previous determination was performed at 153？K [8]. The total lattice energy has also been calculated and this is divided into the corresponding Coulombic, polarization, dispersion, and repulsion energies [9]. The molecular pairs (in the crystal packing) were extracted and their energies were compared with the values obtained from high level DFT + disp calculations at the crystal geometry with BSSE [10] corrections. The lattice energy obtained from the PIXEL has been compared with the value achieved from Crystal
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