1-(2-Fluorobenzyl)-1-(2-fluorobenzyloxy)urea

Abstract

In the title hydroxy­urea derivative, C15H14F2N2O2, the dihedral angle between the two benzene rings is 48.64 (19)°. The urea group forms dihedral angles of 48.1 (2) and 79.2 (2)° with the two benzene rings. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds occur, and further N—H⋯O links lead to chains of molecules.

Crystal structure of 1-(benzyloxy)urea, C8H10N2O2

“…In the title crystal structure, the conformations of the N-Oand C=O bonds are anti to each other (figure, top), similar to that observed in 1-(2-fluorobenzyl)-1-(2-fluorobenzyloxy)urea [1], Nhydroxyurea [2][3][4][5], 1-hydroxy-1-methylurea and 1-hydroxy-3-methylurea [6]. The length of the carbonyl bond (C=O) in above hydroxyurea derivates [2][3][4][5][6] is longer (> 1.25 Å), but the values observed in the title compound is in the normal range of 1.19 -1.23 Å and obviously shorter (< 1.25 Å).…”

“…The length of the carbonyl bond (C=O) in above hydroxyurea derivates [2][3][4][5][6] is longer (> 1.25 Å), but the values observed in the title compound is in the normal range of 1.19 -1.23 Å and obviously shorter (< 1.25 Å). This may be related with the hydroxyl group etherification, which suggests that the structure has not an Hatom of hydroxyl group to form intramolecular hydrogen bonding with O2.…”

Crystal structure of 1-(4-chlorobenzyloxy)-3-phenylurea, C14H13ClN2O2

“…In the title crystal structure, the bond length of the carbonyl bond (C=O) is 1.225 Å which is in the normal range of 1.19 -1.23 Å, similar to that observed in our previous papers [2][3][4]. There are three significant atomic planes in the structure, two benzene rings and the urea plane (O1, N1, N2, C1).…”

1-(3-Chlorobenzyloxy)urea

“…For general background to the design and synthesis of hydroxyurea derivatives and their in vitro antitumor activity, see: Mai et al (2009). For related structures, see: Armagan et al (1976); Nielsen et al (1993); Berman & Kim (1967); Howard et al (1967); Larsen & Jerslev (1966); Thiessen et al (1978); Yoshitaka et al (1993).…”

“…Hydroxyurea (HU) is a substance used in cancer chemotherapy for many years, but it has several disadvantages, such as short half-life, extremely polar nature, the rapid development of resistance and so on. To obtain more potent compound, we have designed and synthesized HU derivatives, and evaluated their in vitro antitumor activities in our previous work (Mai et al, 2009). Here we report the crystal structure of the title compound, 3-chlorobenzyloxyurea.…”