Crystal structure and Hirshfeld surface analysis of 2-(4-chlorophenyl)-4-(dimethoxymethyl)-5-phenyl-1,3-thiazole

In the title compound, the dihedral angles between the thiazole ring and its attached chlorophenyl and phenyl rings are 13.12 (14) and 43.79 (14)°, respectively.


Chemical context
Thiazole and its derivatives have attracted much synthetic interest due to their antimicrobial, antiviral, anti-diabetic, diuretic, anticonvulsant, antioxidant, anti-HIV, analgesic, antiinflammatory, neuroprotective and antitumor activities (Dondoni 2010;Grover & Jachak 2015). In fact, the thiazole moiety is a prominent structural feature in a variety of natural products, such as vitamin B and penicillin (Yariv et al., 2015). On the other hand, the thiazole synthon is also useful in coordination chemistry and catalytic transformations due to its coordination ability and non-covalent bond donor or acceptor character (Gurbanov et al., 2020). As part of our studies in this area, we now report the synthesis and structure of the title compound and quantify its intermolecular noncovalent interactions by Hirshfeld surface analysis.

Supramolecular features and Hirshfeld surface analysis
The extended structure features C-HÁ Á Á interactions, forming a three-dimensional network (Table 1, Fig. 2) in which the thiazole ring accepts once such bond and the phenyl ring two, but no significantstacking contacts are observed [shortest centroid-centroid separation = 4.1887 (16) Å ]. A Hirshfeld surface analysis was performed, and two-dimensional fingerprint plots were created with Crystal Explorer17.5 (Turner et al., 2017) to quantify the intermolecular interactions present in the extended structure. Fig. 3 depicts the Hirshfeld surface projected on d norm and the related colours reflecting various interactions. The C-HÁ Á ÁCl interaction is represented by the red spot on the surface. Fig. 4 depicts the two-dimensional fingerprint plots. The weak van der Waals HÁ Á ÁH connections provide the most (39.2%, Fig. 4b) to the Hirshfeld surface. The other principal contributions to the overall surface are from CÁ Á ÁH/HÁ Á ÁC (25.2%, Fig. 4c), ClÁ Á ÁH/HÁ Á ÁCl (11.4%, Fig. 4d) and OÁ Á ÁH/HÁ Á ÁO (8.0%, Fig. 4e) interactions. The contributions of the remaining less important interactions are given in Table 2.

Figure 2
The packing viewed along the a-axis direction with the C-HÁ Á Á interactions indicated by dashed lines.

Figure 3
The three-dimensional Hirshfeld surface for the title compound, plotted over d norm in the range À0.08 to +1.30 a.u.
In the crystal of (I), the thiazolidinyl ring (r.m.s. deviation = 0.024 Å ) forms a dihedral angle of 65.13 (8) with the attached phenyl ring. The molecular packing features C-HÁ Á ÁO and C-HÁ Á Á interactions, forming a three-dimensional network. In (II), molecules form extended chains through O-HÁ Á ÁN hydrogen bonds and in (III), the two independent molecules are associated via complementary N-HÁ Á ÁN hydrogen bonds into a dimer. These dimers are associated through weak C-HÁ Á ÁCl and C-HÁ Á ÁS interactions into supramolecular chains propagating along the a-axis direction. In (IV), the molecules are linked via C-HÁ Á ÁO interactions, which form C(7) chains propagating along [010]. In addition to this, weakinteractions are also observed.

Refinement details
Crystal data, data collection and structure refinement details are summarized in Table 3    CrysAlis PRO (Rigaku OD, 2022); program(s) used to solve structure: SHELXT2016/6 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2020). where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max = 0.001 Δρ max = 0.67 e Å −3 Δρ min = −0.52 e Å −3 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. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > 2sigma(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.