Crystal structure and Hirshfeld surface analysis of N-{[5-(4-methylphenyl)-1,2-oxazol-3-yl]methyl}-1-phenyl-N-(prop-2-en-1-yl)methanesulfonamide

Molecules in the crystal are joined together by C—H—O hydrogen bonds, forming a three-dimensional network


Chemical context
Sulfonamide antibiotics are readily available drugs that are gradually losing their importance due to the development of bacterial resistance (Skö ld, 2000). Along with the use of much less accessible antibiotics of other classes, the design of new sulfonamides to overcome this problem seems to be reasonable (Nadirova et al., 2021;Naghiyev et al., 2020). One of the possible methods for structural modification is the synthesis of drug analogues containing heterocycles. From this point of view, isothiazole (Kletskov et al., 2020;Khalilov et al., 2021) and isoxazole (Zhu et al., 2018;Abdelhamid et al., 2011) rings are of great interest. In particular, isoxazole derivatives possess a wide range of biological activity, so this heterocycle is considered to be one of the most privileged scaffolds in pharmaceutical chemistry (Altug et al., 2017;Safavora et al., 2019). Moreover, a lot of isoxazoles exhibit antibacterial properties on their own (Agrawal & Mishra, 2018;Yadigarov et al., 2009), and the widely used sulfonamide antibiotic sulfamethoxazole contains an isoxazole ring. A preliminary assessment of the biological activity of newly designed isoxazole-containing structures can be carried out in silico using molecular docking. Data on the structural parameters of promising molecules is therefore required (Gurbanov et al., 2020a,b;Ma et al., 2020Ma et al., ,2021. All this was our motive for the synthesis and accurate structure establishment of N-allyl-N-[(5-tolylisoxazol-3-yl)methyl]benzylsulfonamide (1), which has not previously been characterized. It was obtained from isoxazolylallylamine (2) and benzyl sulfonyl chloride using the 'green chemistry' procedure developed earlier by one of us (Kolesnik et al., 2022).
Allyl derivatives structurally similar to sulfonamide 1 are widely used as starting materials in organic synthesis for the construction of polyheterocyclic systems through intramolecular [4 + 2] cycloaddition reactions (Zubkov et al., 2014;Krishna et al., 2022).

Supramolecular features and Hirshfeld surface analysis
Molecules in the crystal are joined together by C-HÁ Á ÁO hydrogen bonds, forming a three-dimensional network (Table 1; Figs. 2, 3 and 4).

Figure 2
A view along the a axis of the C-HÁ Á ÁO interactions in the title compound.

Figure 1
The title molecule with the labelling scheme and 50% probability ellipsoids.
In the crystal of CEGKAC, molecules are linked by N-HÁ Á ÁO hydrogen bonds, generating C(10) chains propagating in [001]. The packing is consolidated by C-HÁ Á ÁO, C-HÁ Á Á and very weak aromaticstacking interactions [centroidcentroid separation = 4.085 (2) Å ]. In the crystal of CICPIO, the molecules are packed into a layer structure along the aaxis direction via N-HÁ Á ÁO hydrogen bonds [HÁ Á ÁO = 2.08 (2), NÁ Á ÁO = 2.911 (6) Å and N-HÁ Á ÁO = 164 (6) ]. In the crystal of WIHGUQ, the amide H atom is available to a receptor molecule as it lies on one side of the plane of the benzene ring, while the methanesulfonyl group is on the opposite side of the plane, similar to the arrangement in other methanesulfonanilides. The molecules are packed into chains through N-HÁ Á ÁO and N-HÁ Á ÁCl hydrogen bonding. In the crystal of VIDKOJ, the molecules are linked into chains along the c-axis direction through N-HÁ Á ÁO hydrogen bonds.   Table 2 Summary of short interatomic contacts (Å ) in the title compound.

Contact
Distance Symmetry operation

Figure 4
A view along the c axis of the C-HÁ Á ÁO interactions in the title compound.

Figure 5
View of the three-dimensional Hirshfeld surface of the title compound plotted over d norm in the range À0.1677 to +1.4857 a.u.

Synthesis and crystallization
A mixture of 1,2-oxazolylallylamine 2 (1 mmol), benzyl sulfonyl chloride (1.2 mmol) and Na 2 CO 3 (1.2 mmol) in water (15 mL) was refluxed for 4 h. After cooling, the reaction mixture was extracted with CH 2 Cl 2 (3 Â 10 mL). The combined organic fractions were washed with water (2 Â 10 mL) and dried over Na 2 SO 4 . The solvent was evaporated under reduced pressure. The resulting oil was purified by flash chromatography (eluent CH 2 Cl 2 ) and crystallized from MeOH as colourless crystals, yield 0.

Refinement details
Crystal data, data collection and structure refinement details are summarized in Table 3. The C-bound H atoms were positioned with idealized geometry and refined using a riding model with C-H = 0.95 Å (CH aromatic), 0.99 Å (CH 2 ) and 0.98 Å (CH 3 ). Isotropic displacement parameters for all H atoms were set equal to 1.2 or 1.5U eq (parent atom). The crystal studied was refined as an inversion twin.   (Farrugia, 2012) and PLATON (Spek, 2020).