(1R,3S)-1,1′-(1,3-Dihydro-2-benzofuran-1,3-diyl)bis(1,3-dimethylurea)

In the molecule of the title compound, C14H20N4O3, the five-membered ring adopts an envelope conformation with the O atom displaced by 0.207 (3) Å from the plane of the other ring atoms. Intramolecular C—H⋯O hydrogen bonds result in the formation of three five-membered rings having envelope conformations. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link the molecules, forming R 2 2(20) ring motifs, which produce two-dimensional polymeric sheets extending along the b axis. There are also two C—H⋯π interactions. The H atoms of one of the methyl groups are disordered over two positions and were refined with occupancies of 0.50.

In the molecule of the title compound, C 14 H 20 N 4 O 3 , the fivemembered ring adopts an envelope conformation with the O atom displaced by 0.207 (3) Å from the plane of the other ring atoms. Intramolecular C-HÁ Á ÁO hydrogen bonds result in the formation of three five-membered rings having envelope conformations. In the crystal structure, intermolecular N-HÁ Á ÁO hydrogen bonds link the molecules, forming R 2 2 (20) ring motifs, which produce two-dimensional polymeric sheets extending along the b axis. There are also two C-HÁ Á Á interactions. The H atoms of one of the methyl groups are disordered over two positions and were refined with occupancies of 0.50.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2591).  (Veeraraghavan et al., 1996). These compounds have several biological activities, such as antioxidant, antimycotic, cytotoxic, antimicrobial, herbicidal, analgesic and pesticidal activities (Lin et al., 2005, Roy & Sarkar, 2005, Harper et al., 2003. These are known to exhibit hypotensive and vasorelaxant properties (Tsi & Tan, 1997). We report herein the synthesis and crystal structure of the title compound.
This study is in countinuation to the formation of derivatives of O-phthaldehyde with different ureas (Maliha et al., 2007;. The molecule of the title compound is essentially symmetric about the mirror plane passing through the O1 atom of the 2-benzofuran ring system as far as the chemical structure is concerned. But, the intramolecular C-H···O hydrogen bonds (Table 1)  In the crystal structure, intermolecular N-H···O hydrogen bonds (Table 1) link the molecules to form R 2 2 (20) ring motifs (Bernstein et al., 1995), which are joint in such a fashion that the 2-benzofuran rings are in cis and trans positions. They produce two dimensional polymeric sheets extending along the b axis (Fig 2). There also exist two C-H···π interactions (Table 1).

Experimental
For the preparation of the title compound, O-phthaldehyde (200 mmol), N,N-dimethylurea (200 mmol) and a few drops of HCl were refluxed in ethanol. Colorless precipitate obtained was crystallized in the solution of methanol:acetone (9:1) by slow evaporation at room temperature.

Refinement
The hydrogen atoms of the C11 methyl group were disordered over two positions. During the refinement process the disordered atoms were refined with occupancies of 0.50. H1, H8 (for CH) and H2N, H4N (for NH) atoms were located in difference syntheses and refined [C-H = 0.987 (17) and 1.003 (17) Å, U iso (H) = 1.2U eq (C); N-H = 0.806 (19) and 0.858 (18) Å, U iso (H) = 1.5U eq (N). The remaining H atoms were positioned geometrically, with C-H = 0.93 and 0.96 Å for aromatic supplementary materials sup-2 and methyl H, respectively, and constrained to ride on their parent atoms with U iso (H) = xU eq (C), where x = 1.5 for methyl H and x = 1.2 for aromatic H atoms. Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines.