(±)-1,2-Bis( N ′-benzoylthioureido)cyclohexane (original) (raw)

2011, Acta Crystallographica Section E Structure Reports Online

The title compound, (I) is similar to 1,2-bis[N'-(2,2-dimethylpropionyl) thioureido]cyclohexane (Yusof et al., 2008) except the two side arms are benzoylthioureido (Fig. 1) groups instead of 2,2-dimethylpropionylthioureido.The bond lengths and angles are in normal ranges (Allen et al., 1987) and comparable to those in 1,2-bis[N'-(2,2dimethylpropionyl)thioureido]cycylohexane and 1,2-bis (N'-benzoylthioureido)benzene (Thiam et al., 2008). However, the dihedral angle between the thiourea groups of 73.09 (9)° is slightly smaller compare to 78.55 (7)° in the propionylthioureido analog. Both thiourea moieties, S1/N2/C7/C8/C9 and S2/N3/N4/C14/C15 are planar with maximum deviation of 0.017 (3)Å for C9 atom from the least square plane. There are two intramolecular hydrogen bonds N2-H2A..O1 and N3-H3A•••O2 forming two pseudo-six membered rings S(6) (Etter et al., 1990; Bernstein et al., 1995) O1•••H2A-N2-C8-N1-C7 and O2..H3A-N3-C15-N4-C16 respectively (Table 1). In the crystal structure, the molecules are linked by intermolecular hydrogen bonds N1-H1A•••O2 forming a R 4 2 (18) graph set motif and N4-H4A•••S2 forming a R 2 2 (8) motif (Etter et al., 1990; Bernstein et al., 1995). These intermolecular interactions result in the formation of chains extending along the b axis (Fig.2; Table 1). Experimental A solution of benzoylisothiocyanate (3.26 g, 0.02 mol) in 30 ml acetone was added into a flask containing 30 ml acetone solution of 1,2-diamino cyclohexane (1.14 g, 0.01 mol).The mixture was refluxed for 1 h. Then, the solution was filtered-off and left to evaporate at room temperature. The colourless solid was obtained after one day of evaporation(yield 81%, m.p 495.3-497.3 K) Refinement H atoms on the parent carbon atoms were positioned geometrically with C-H= 0.96-0.98 Å and constrained to ride on their parent atoms with U iso (H)= xU eq (parent atom) where x=1.5 for CH 3 group and 1.2 for CH 2 and CH groups.