Synthesis and crystal structure of N-phenyl-2-(phenylsulfanyl)acetamide

In the crystal of the title compound, N—H⋯O hydrogen bonds form chains of molecules along the [100] direction. The chains are linked by C—H⋯π interactions, forming a three-dimensional network.

N-Phenyl-2-(phenylsulfanyl)acetamide, C 14 H 13 NOS, was synthesized and structurally characterized.In the crystal, N-H� � �O hydrogen bonding leads to the formation of chains of molecules along the [100] direction.The chains are linked by C-H� � �� interactions, forming a three-dimensional network.The crystal studied was twinned by a twofold rotation around [100].
Additionally, the evolution of the pharmaceutical industry has been greatly aided by the discovery of sulfur-based therapies.Sulfur-derived functional groups can be found in a broad range of natural products and pharmaceuticals.Sulfur remains the dominant heteroatom integrated into a variety of FDA-approved sulfur-containing medications (Feng et al., 2016).
Sulfides have been presented inter alia as precursors for sulfonyl chloride synthesis (Langler et al., 1979).Advanced methods previously reported for the transformation of sulfides include, for example, using sulfate-modified multi-walled carbon nanotubes (S-MWCNT) and mesoporous carbon (S-MC) as heterogenous catalysts to facilitate the synthesis of acetamide derivatives (Minchitha et al., 2018).
Herein, we report the first synthesis of a sulfide from a sulfonyl derivative via an alternative new, direct and efficient approach.Upon reaction of the sulfonylguanidine derivative with 2-chloro-N-phenylacetamide, the title compound Nphenyl-2-(phenylsulfanyl)acetamide ( 3) is formed.Its chemical structure was confirmed by spectroscopic techniques and elemental analysis.The 1 H NMR spectrum has a singlet signal of the methylene group at � 3.84 ppm, the multiplet aromatic protons at � 7.30 ppm, as well as the amine proton at � 9.15 ppm, which is roughly in accordance with previously reported data (Motherwell et al., 2002).Confirmation of the molecular structure is provided by means of single crystal X-ray diffraction structural analysis which provides the first crystal structure and geometric parameters for the title compound.

Supramolecular features
The packing in the crystal structure of 3 is shown in Fig. 2a.In the crystal, the acetamide groups of each set of independent molecules interact through weak N-H� � �O contacts (Table 1), forming chains parallel to [100] (Fig. 2b).
Adjacent chains are linked by weak C-H� � �� contacts between methylene and phenyl groups.

Database survey
A search of the CSD (version 5.44, April 2023;Groom et al., 2016) using the routine ConQuest (Bruno et al., 2002)

Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2.The crystal studied was twinned by a twofold rotation around [100].This problem was addressed using a HKLF5 file for refinement.The N-bound hydrogen atoms were refined with regard to location while the displacement parameters were constrained to those of their parent atoms [U iso (H) = 1.2U eq (N)].All other hydrogen atoms were placed in idealized positions (C-H = 0.93-0.97A ˚) and refined using a riding model with U iso (H) = 1.2U eq (C).The synthesis of compound 3 from sulfonylguanidine.

Special details
Experimental.Single-crystal XRD data were collected at room temperature on an Agilent SuperNova Dual Atlas diffractometer using mirror-monochromated Mo Kα radiation.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.Refinement.Refined as a 2-component twin.

Figure 1
Figure 1The asymmetric unit and molecular structures of the two independent molecules of N-phenyl-2-(phenylsulfanyl)acetamide (3) showing displacement ellipsoids at the 50% probability level.

Figure 2 (
Figure 2 (a) Crystal packing in the crystal structure of N-phenyl-2-(phenylsulfanyl)acetamide (3).(b) A segment of the crystal structure of compound 3 showing the N-H� � �O and C-H� � �� intermolecular contacts as green dotted lines.

Table 2
Experimental details.