Crystal structure and Hirshfeld surface analysis of (Z)-4-{[4-(3-methyl-3-phenylcyclobutyl)thiazol-2-yl]amino}-4-oxobut-2-enoic acid

The title compound is a cyclobutyl compound that adopts a Z configuration. The molecular structure is stabilized by an N—H⋯O hydrogen bond, forming an (7) ring motif. In the crystal, molecules are linked by pairs of O—H⋯N hydrogen bonds, forming supramolecular ribbons linked via C 1 1(9) ring motifs.


Structural commentary
The title cyclobutyl derivative crystallizes in the orthorhombic P2 1 2 1 2 1 space group with Z 0 = 1. Its molecular structure is ISSN 2056-9890 illustrated in Fig. 1, showing the intramolecular N-HÁ Á ÁO hydrogen bond forming an S 1 1 (7) ring motif. The molecule is non-planar as the thiazole and benzene rings are twisted with respect to each other, subtending a dihedral angle of 88.29 (11) . In addition, the cyclobutyl ring is twisted by 58.1 (2) and 40.2 (2) , with respect to the thiazole, and benzene rings. In the thiazole ring, the C12-N1 bond length is 1.386 (4) Å and classified as a single bond.
The cyclobutane adopts a puckered (butterfly) conformation. The average carbon-carbon (C-C) bond lengths within the ring is 1.5506 Å , with average C-C-C bond angles of 88.89 , while the average torsion angle within the C 4 ring is 15.83 . When these parameters are compared with the recently published cyclobutane derivatives (Gumus et al., 2021), it is seen that there are no considerable differences. The S1-C13 and S1-C14 bond lengths are 1.727 (4) and 1.716 (3)

Figure 1
The molecular structure of the title compound with displacement ellipsoids drawn at the 40% probability level. Dashed lines denote the intramolecular N-HÁ Á ÁO hydrogen bonds forming an S 1 1 (7) ring motif.

Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2. Although the acidic protons from the O-H and N-H bonds could be located in the difference-Fourier map, even very strong distance restraints were not sufficient to obtain proper distances between the parent atom and hydrogen. Therefore, both protons were refined in geometrical positions using the corresponding AFIX instructions with O-H = 0.82 Å and U iso (H) = 1.5U eq (O), and N-H = 0.86 Å and U iso (H) = 1.2U eq (N), respectively. The C-bound H atoms were positioned geometrically (C-H = 0.93, 0.96, 0.97 and 0.98 Å ) and refined using a riding model, with U iso (H) = 1.5U eq (C) for methyl H atoms and 1.2U eq (C) for other H atoms. The synthesis of (Z)-4-{[4-(3-methyl-3-phenylcyclobutyl)thiazol-2yl]amino}-4-oxobut-2-enoic acid.   (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2020).

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.