Abstract
In the title compound, C23H17ClN2O3, the 2,3-dihydro-1H-indene ring system (r.m.s deviation = 0.004 Å) subtends dihedral angles of 81.12 (16) and 7.56 (14)° with the chlorophenyl and benzene rings, respectively. The molecular conformation features an intramolecular O—H...O hydrogen bond, forming an S(6) ring motif. In the crystal, molecules are linked by N—H...O hydrogen bonds generating [100] chains featuring R 1 2(6) loops. Weak aromatic π–π stacking [centroid–centroid distance = 3.656 (2) Å] is also oberved.
Highlights
In the title compound, C23H17ClN2O3, the 2,3-dihydro-1H-indene ring system (r.m.s deviation = 0.004 A ) subtends dihedral angles of 81.12 (16) and 7.56 (14) with the chlorophenyl and benzene rings, respectively
Molecules are linked by N—HÁ Á ÁO hydrogen bonds generating [100] chains featuring R21(6) loops
The N—(C O)—N plane involving the urea group is oriented at dihedral angles of 54.36 (17), 40.01 (15) and 56.15 (14), respectively, with the chlorophenyl ring, the benzene ring and the 2,3-dihydro-1H-indene ring system, respectively
Summary
Organic compounds containing the phenylurea unit are known to be valuable in terms of biological activity (Jiang et al, 2016; Sikka et al, 2015). As part of our studies in this area, we new report the crystal structure (Fig. 1) of the title compound (Gezegen et al, 2017). The 2,3-dihydro-1H-indene ring system (C15–C23) is essentially planar (r.m.s deviation = 0.004 A ), and is inclined at dihedral angles of 81.12 (16) and 7.56 (14) with the chlorophenyl (C1–C6) and benzene (C8–C13) rings, respectively. The N—(C O)—N plane involving the urea group is oriented at dihedral angles of 54.36 (17), 40.01 (15) and 56.15 (14), respectively, with the chlorophenyl ring, the benzene ring and the 2,3-dihydro-1H-indene ring system, respectively.
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