Hirshfeld surfaces and two-dimensional fingerprint plots are used to study short intermolecular contacts in new organotin(IV)-phosphoramide complexes, (L1)2Cl2Me2Sn (1), (L2)Cl2Me2Sn (2) and (L3)2Cl2Me2Sn (3) [L1 = (C5H9NH)3PO, L2 = [(CH3)3CNH][C6H5CH2N(CH3)]2PO and L3 = (3-F-C6H4C(O)NH)(N(CH3)C6H11)2PO]. The previously reported structure L3 is also analyzed for a comparison with the related complex, 3. While 2 and 3, respectively, contain one independent molecule and one-half of a molecule, the asymmetric unit of 1 is composed of three independent molecules with different conformations of ligands around the tin center but with very similar Hirshfeld surfaces and fingerprint plots. The SnIV coordination geometries are octahedral for 1 and 3 with cis-phosphoramides in each independent molecule of 1 and trans-phosphoramides in 3. For 2, the SnIV adopts a distorted trigonal bipyramidal environment with the axial positions occupied by the ligand phosphoramide and one Cl atom. Two-dimensional fingerprint plots of 1 and 2 show pairs of spikes attributed to the intermolecular H…Cl contacts including N—H…Cl hydrogen bonds. Two spikes found in 3 are much shorter comparing with 1 and 2 due to absence of the intermolecular N—H…Cl hydrogen bond and lower contribution of C—H…Cl contacts. In the ligand L3 the presence of N—H…O═P hydrogen bond is reflected as a deep-red area of Hirshfeld surfaces. Moreover, in fingerprint plot of L3 two intense spikes are observed related to the intermolecular H…O contacts including N—H…O═P hydrogen bond. The more shallow red spots on the Hirshfeld surface of 3 with respect to L3 are caused by absence of N—H…O hydrogen bond and the lower contribution of H…O contacts.

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