Crystal structure of catena-poly[[(N,N-diethyl-3-mesitylsulfonyl-1H-1,2,4-triazole-1-carboxamide-κN 1)silver(I)]-μ-nitrato-κ3 O,O′:O]

The asymmetric unit of the title compound comprises one cafenstrole ligand molecule and one silver nitrate ion. The coordination bonds between silver and oxygen atoms allow a continuous one-dimensional coordination polymer structure along [001]. The three-dimensional architecture is stabilized by C—H⋯O hydrogen bonds and C—H⋯π interactions

The reaction of silver nitrate and cafenstrole (N,N-diethyl-3-mesitylsulfonyl-1H-1,2,4-triazole-1-carboxamide), a triazole herbicide, leads to the title coordination polymer, [Ag(NO 3 )(C 16 H 22 N 4 O 3 S)] n , whose asymmetric unit comprises one cafenstrole ligand molecule, one Ag I atom and one nitrate ion. The Ag I atom, with a distorted trigonal-pyramidal environment, is coordinated by one nitrogen atom of a triazole ring, two oxygen atoms of a nitrate ion and one oxygen atom of a neighboring nitrate ion. The coordination bonds between silver and oxygen atoms give rise to a one-dimensional (1D) coordination polymer structure along [001]. The dihedral angle between the planes of the triazole and benzene rings is 87.13 (11) . In the crystal, the coordination polymer is stabilized by C-HÁ Á ÁO hydrogen bonds and C-HÁ Á Á interactions, resulting in a three-dimensional architecture.

Chemical context
Recently, we have reported the crystal structure of the ligand cafenstrole (L; Kang et al., 2015). Cafenstrole is a triazole herbicide and has been used for rice cultivation as an inhibitor of the germination of grass weeds (Takahashi et al., 2001). Triazole derivatives have been investigated intensively over the years for pharmaceutical and agricultural purposes (Kumar et al., 2013;Zhang et al., 2014). It is very likely that triazole-metal interactions play a major role in the biological actions of triazole-containing drugs and agricultural chemicals. 1,2,4-Triazole and its derivatives have gained great attention as ligands to transition metals (Haasnoot, 2000). To understand the interactions of triazoles with metals, further research on the structures of triazole-metal compounds is of great necessity. Thus, our attention will be focused on the diversity of the coordination geometries of 1,2,4-triazole complexes with transition metal ions. Herein, we report the reaction of silver nitrate and cafenstrole to produce the title compound, which is a 1D silver(I) coordination polymer.
Atom Ag1 lies almost in the plane constituted by atoms O5, N1, and O5 i [deviation = 0.0436 (12) Å ]. The Ag1, O5, N1, and O5 i atoms form a slightly distorted triangular basal plane with bond angles O5-Ag1-O5 i = 106.52 (5), O5-Ag1-N1 = 118.75 (11) and O5 i -Ag1-N1 = 134.63 (11) . The apex atom, O4, deviates considerably from the normal to the basal plane, as indicated by the O4-Ag1-N1 bond angle of 149.66 (10) . Other bond angles are 48.93 (10) and 67.18 (10) for O4-Ag1-O5 and O4-Ag1-O5 i , respectively. One oxygen atom of the nitrate ion (O6) is not bound to the Ag I ion, whereas the other two oxygen atoms of the nitrate ion (O4 and O5) are bound to the Ag I ion. One of the bound O atoms (O5) links neighbouring Ag I ion ions, thus forming a 1D polymer along [001]. The triazole plane is rotated about the S1-C10 axis in the opposite direction in comparison with free cafenstrol (Kang et al., 2015). Thus, the diethyl amino group is located above the phenyl ring in the title compound, while that of free cafenstrol is placed outside the phenyl ring.

Supramolecular features
The O5 atom is bound to both Ag1 and neighboring Ag1 ii [symmetry code: (ii) Àx + 1, Ày + 1, z + 1 2 ], where the neighbouring asymmetric unit is related to the asymmetric unit by 2 1 symmetry, resulting in a 1D chain along [001] (Fig. 3). C-HÁ Á ÁO hydrogen bonds between the 1D chains (yellow dashed lines) lead to the formation of layers parallel to (100). The layers are packed in an ABAB pattern along [010] (Fig. 4). Weak intermolecular C-HÁ Á Á interactions (black dashed lines) between the A and B layers generate a three-dimensional network structure (Fig. 4). Thus the structure of the Ag I coordination polymer is stabilized by C13-H13BÁ Á ÁO2 and The coordination environment of the Ag I atom in the title compound.

Figure 3
The packing of the title compound showing chains along [001].

Figure 1
The asymmetric unit of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius.

Synthesis and crystallization
The title compound was prepared from a mixed solution of the cafenstrole ligand (0.05 g, 0.14 mmol) in acetone (5 mL) and Ag(NO 3 ) (0.06 g, 0.35 mmol) in methanol (5 mL). The ligand was purchased from the Dr Ehrenstorfer GmbH Company. Single crystals suitable for X-ray crystallography were obtained by slow evaporation of the solvent at room temperature after one week.

catena-Poly[[(N,N-diethyl-3-mesitylsulfonyl-1H-1,2,4-triazole-1-carboxamide-κN 1 )silver(I)]-µ-nitrato-κ 3 O,O′:O]
Crystal data Special details Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.