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(E)-{[(Butyl-sulfan-yl)methane-thio-yl]amino}(4-meth-oxy-benzyl-idene)amine: crystal structure and Hirshfeld surface analysis.

ABSTRACT: The title hydrazine carbodi-thio-ate, C13H18N2OS2, is constructed about a central and almost planar C2N2S2 chromophore (r.m.s. deviation = 0.0263 Å); the terminal meth-oxy-benzene group is close to coplanar with this plane [dihedral angle = 3.92 (11)°]. The n-butyl group has an extended all-trans conformation [torsion angles S-Cm-Cm-Cm = -173.2 (3)° and Cm-Cm-Cm-Cme = 180.0 (4)°; m = methyl-ene and me = meth-yl]. The most prominent feature of the mol-ecular packing is the formation of centrosymmetric eight-membered {⋯HNCS}2 synthons, as a result of thio-amide-N-H⋯S(thio-amide) hydrogen bonds; these are linked via meth-oxy-C-H⋯π(meth-oxy-benzene) inter-actions to form a linear supra-molecular chain propagating along the a-axis direction. An analysis of the calculated Hirshfeld surfaces and two-dimensional fingerprint plots point to the significance of H⋯H (58.4%), S⋯H/H⋯S (17.1%), C⋯H/H⋯C (8.2%) and O⋯H/H⋯O (4.9%) contacts in the packing. The energies of the most significant inter-actions, i.e. the N-H⋯S and C-H⋯π inter-actions have their most significant contributions from electrostatic and dispersive components, respectively. The energies of two other identified close contacts at close to van der Waals distances, i.e. a thione-sulfur and meth-oxy-benzene-hydrogen contact (occurring within the chains along the a axis) and between methyl-ene-H atoms (occurring between chains to consolidate the three-dimensional architecture), are largely dispersive in nature.

SUBMITTER: Rusli AF

PROVIDER: S-EPMC7001837 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

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(E)-{[(Butyl-sulfan-yl)methane-thio-yl]amino}(4-meth-oxy-benzyl-idene)amine: crystal structure and Hirshfeld surface analysis.

Rusli Aqilah Fasihah AF Kwong Huey Chong HC Crouse Karen A KA Jotani Mukesh M MM Tiekink Edward R T ERT

Acta crystallographica. Section E, Crystallographic communications 20200117 Pt 2

The title hydrazine carbodi-thio-ate, C13H18N2OS2, is constructed about a central and almost planar C2N2S2 chromophore (r.m.s. deviation = 0.0263 Å); the terminal meth-oxy-benzene group is close to coplanar with this plane [dihedral angle = 3.92 (11)°]. The n-butyl group has an extended all-trans conformation [torsion angles S-Cm-Cm-Cm = -173.2 (3)° and Cm-C ...[more]

PMID: 32071748

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Project description:The title hydrazine carbodi-thio-ate chloro-form hemisolvate, 2C15H14N2O2S2·CHCl3, comprises two independent hydrazine carbodi-thio-ate mol-ecules, A and B, and a chloro-form mol-ecule; the latter is statistically disordered about its mol-ecular threefold axis. The common features of the organic mol-ecules include an almost planar, central CN2S2 chromophore [r.m.s. deviation = 0.0203 Å (A) and 0.0080 Å (B)], an E configuration about the imine bond and an intra-molecular hydroxyl-O-H⋯N(imine) hydrogen bond. The major conformational difference between the mol-ecules is seen in the relative dispositions of the phenyl rings as indicated by the values of the dihedral angles between the central plane and phenyl ring of 71.21 (6)° (A) and 54.73 (7)° (B). Finally, a difference is seen in the disposition of the outer hydroxyl-H atoms, having opposite relative orientations. In the calculated gas-phase structure, the entire mol-ecule is planar with the exception of the perpendicular phenyl ring. In the mol-ecular packing, the A and B mol-ecules assemble into a two-mol-ecule aggregate via N-H⋯S hydrogen bonds and eight-membered {⋯HNCS}2 synthons. The dimeric assemblies are connected into supra-molecular chains via hydroxyl-O-H⋯O(hydrox-yl) hydrogen bonds and these are linked into a double-chain through hy-droxy-O-H⋯π(phen-yl) inter-actions. The double-chains are connected into a three-dimensional architecture through phenyl-C-H⋯O(hydrox-yl) and phenyl-C-H⋯π(phen-yl) inter-actions. The overall assembly defines columns along the a-axis direction in which reside the chloro-form mol-ecules, which are stabilized by chloro-form-methine-C-H⋯S(thione) and phenyl-C-H⋯Cl contacts. The analysis of the calculated Hirshfeld surfaces, non-covalent inter-action plots and inter-action energies confirm the importance of the above-mentioned inter-actions, but also of cooperative, non-standard inter-actions such as π(benzene)⋯π(hydrogen-bond-mediated-ring) contacts.

Dataset Information

(E)-{[(Butyl-sulfan-yl)methane-thio-yl]amino}(4-meth-oxy-benzyl-idene)amine: crystal structure and Hirshfeld surface analysis.

Publications

(<i>E</i>)-{[(Butyl-sulfan-yl)methane-thio-yl]amino}(4-meth-oxy-benzyl-idene)amine: crystal structure and Hirshfeld surface analysis.

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