Butyl 2-(3-benzoylthioureido)acetate (original) (raw)

2008, Acta Crystallographica Section E Structure Reports Online

The title compound (I) is a thiourea derivative of glycine analogous to ethyl-2-(3-benzoylthioureido)acetate (II) (Hassan et al., 2008a) and propyl-2-(3-benzoylthioureido)acetate (III) (Hassan et al., 2008b), with the shorter alkyl groups replaced by a butyl group. The molecule maintains the same cis-trans configuration with respect to the positions of the butyl acetate and benzoyl groups, relative to the S atom across the C-N bonds (Fig. 1 and Fig. 2), respectively. There is a disorder in the molecules involving the terminal butyl carbon atom. 'Soft' restrains, SIMU and EADP, were applied to the disorder components, C14 and C14', to resolve the overlapping components. In the final refinement the main disorder component, C14, resides in about 80% occupancy whereas the minor component, C14', occupies 20% at a time. The compound was synthesized by a similar procedure to that of reported in (II). The bond lengths and angles in the molecules are in normal ranges (Allen et al., 1987) and comparable to those in II and III. The phenyl ring, (C1-C6), and the central fragment, (C6/C7/C8/C9/N1/N2/S1), are essentially planar and the dihedral angle between them is 27.82 (9)°. In the butyl fragment, (C11/C12/C13/O3), the maximum deviation from the mean plane is 0.017 (3)Å for the atom C12. The dihedral angle between the phenyl ring and the butyl group is 14.5 (3)°. The intramolecular N2-H2•••O1 and C9-H9B•••S1 hydrogen bonds, (Table 1), force the molecule to adopt the present molecular conformation. The intermolecular N1-H1B•••O2 and C2-H4A•••O1 hydrogen bonds, (Table 2), link the molecules into a chain parallel to the c axis (Fig. 3). Experimental Preparation of the compound was carried out according to a previously reported experimental procedures (Hassan et al., 2008a). A yellowish crystal, suitable for X-ray crystallography, was obtained by a slow evaporation from CH 2 Cl 2 solution at room temperature (yield 75%). Refinement All H atoms were positioned geometrically and allowed to ride on their parent atoms, with, U iso =1.2U eq (N) for NH 0.86 Å, U iso =1.2U eq (C) for aromatic 0.93 Å, U iso = 1.2U eq (C) for CH 2 0.97 Å and U iso = 1.5U eq (C) for CH 3 0.96 Å. The disordered component of the butyl group, C14 and C14', was resolved by applying SIMU and EADP constrains and refined anisotropically.