Synthesis, crystal structure and Hirshfeld surface analysis of 2-({5-[(naphthalen-1-yl)methyl]-4-phenyl-4H-1,2,4-triazol-3-yl}sulfanyl)-1-(4-nitrophenyl)ethanone

In the title compound, C27H20N4O3S, the three aromatic rings are oriented almost perpendicular to the plane of the central 1,2,4-triazole ring.

In addition to their bioactivities, naphthalene derivatives are recognized for their antimicrobial, anticancer (Salahuddin et al., 2014), anti-inflammatory (Kaushik et al., 2012), and antidepressant (Kumar et al., 2018) properties.Given the diverse bioactivities associated with both 1,2,4-triazole and naphthalene, we embarked on synthesizing a compound containing both moieties through the S N 2 reaction.Herein we report the crystal structure and Hirshfeld surface analysis of the title compound, C 27 H 20 N 4 O 3 S, obtained during our efforts to synthesize new compounds that contain a 4-phenyl-4H-1,2,4triazole unit.

Structural commentary
The title compound crystallizes in the monoclinic space group P2 1 /n with one molecule in the asymmetric unit (Fig. 1).The

Supramolecular features
The crystal packing of the title compound is characterized by S� � �O interactions between neighboring molecules [O9� � �S6 i = 3.115 (3) A ˚; S6� � �O9 ii = 3.115 (3) A ˚; symmetry codes: (i) , resulting in the formation of chains with a C(4) graph-set motif running in the b-axis direction (Fig. 2).No classical hydrogen bonds are observed.Despite the presence of multiple aromatic rings, the packing shows no strong �-� or C-H� � �� interactions.The shortest distance between aromatic rings is observed for rings C10-C15 and C27-C32, resulting in the formation of inversion dimers.The centroid-centroid distance is 4.105 (2) A ˚, the dihedral angle between the planes is 6.39 (18) � , and the slippage is 1.708A ˚(Fig. 3).

Figure 3
Partial crystal packing of the title compound, showing the �-� stacking.
To visualize the intermolecular interactions in the crystal packing in more detail, a Hirshfeld surface (HS) analysis (Hirshfeld, 1977) was carried out with Crystal Explorer 21.3 (Spackman et al., 2021).In the HS plotted over d norm (Fig. 4), a number of short contacts (shorter than the sum of the van der Waals' radii) are visible as red spots.Further details are given in Table 1.

Database survey
A search of the Cambridge Structural Database (CSD, Version 5.44, update of September 2023; Groom et al., 2016) for the 4-phenyl-4H-1,2,4-triazol-3-ylthio fragment resulted in 70 hits (for refcodes, see supporting information).All 1,2,4triazole rings are planar (maximum deviation from planarity is 0.010 A ˚), with the sulfur atom being nearly in the same plane (maximum deviation of 0.163 A ˚).The dihedral angle between the best planes through the triazole and phenyl ring shows a roughly uniform distribution between 52 and 90 � .For the title compound this angle is 77.14 (18) � .

Synthesis and crystallization
The reaction scheme for the synthesis of the title compound is illustrated in Fig. 6.

Figure 5
The for 5 h, and upon cooling, it was poured into ice-water.The resulting solid was filtered off and recrystallized from a 1:1 mixture of ethanol and water to give the title compound 3 as plate-like yellow crystals (yield: 76.8%, m.p: 454.5 K).

Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2.All hydrogen atoms bound to carbon were placed at idealized positions and refined in riding mode, with U iso (H) values assigned as 1.2U eq of the parent atoms, with C-H distances of 0.93 (aromatic) and 0.97 A (CH 2 ).

Funding information
LVM thanks the Hercules Foundation for supporting the purchase of the diffractometer through project AKUL/09/ 0035.

Figure 6
Reaction scheme for the synthesis of the title compound.Compound 1 was identified as the thione by X-ray crystallography, although IR spectra indicate coexistence of the thione and thiol forms in solution (Le et al., 2023).

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.
Figure 1A view of the molecular structure of the title compound, with atom labels and displacement ellipsoids drawn at the 30% probability level.H atoms are shown as small circles of arbitrary radii.

Figure 4
Figure 4Views of the three-dimensional Hirshfeld surface of the title compound plotted over d norm in the range À 0.1286 to 1.6073 a.u.
full two-dimensional fingerprint plots for the title compound, showing (a) all interactions, and delineated into (b) H� � �H, (c) H� � �O/ O� � �H, (d) H� � �C/ C� � �H, (e) H� � �N/N� � �H, and (f) C� � �C interactions.The d i and d e values are the closest internal and external distances (in A ˚) from given points on the Hirshfeld surface.

Table 2
Experimental details.