(N′,N′′Z,N′,N′′E)-N′,N′′-[1-(4-Chlorophenyl)ethane-1,2-diylidene]bis(3-methyl-1-benzofuran-2-carbohydrazide)

In the title compound, C28H21ClN4O4, the benzofuran ring systems make dihedral angles of 7.43 (8) and 30.92 (9)° with the chloro-substituted benzene ring. The dihedral angle between the two benzofuran ring systems is 27.41 (7)°. The two benzofuran rings are connected to the chloro-substituted benzene ring through C—N—N=C and C—N—N=C—C bridges which are nearly planar [maximum deviations = 0.003 (1) and 0.037 (1) Å]. An intramolecular N—H⋯N hydrogen bond generates an S(6) ring motif. In the crystal, molecules are linked by N—H⋯(O,N) and C—H⋯O hydrogen bonds into a tape along the c axis and these tapes are further connected by another weak C—H⋯O hydrogen bond into a sheet parallel to the bc plane. π–π interactions [centroid-to-centroid distances = 3.4845 (12)–3.6250 (13) Å] are also observed.

In the title compound, C 28 H 21 ClN 4 O 4 , the benzofuran ring systems make dihedral angles of 7.43 (8) and 30.92 (9) with the chloro-substituted benzene ring. The dihedral angle between the two benzofuran ring systems is 27.41 (7) . The two benzofuran rings are connected to the chloro-substituted benzene ring through C-N-N C and C-N-N C-C bridges which are nearly planar [maximum deviations = 0.003 (1) and 0.037 (1) Å ]. An intramolecular N-HÁ Á ÁN hydrogen bond generates an S(6) ring motif. In the crystal, molecules are linked by N-HÁ Á Á(O,N) and C-HÁ Á ÁO hydrogen bonds into a tape along the c axis and these tapes are further connected by another weak C-HÁ Á ÁO hydrogen bond into a sheet parallel to the bc plane.interactions [centroid-to-centroid distances = 3.4845 (12)-3.6250 (13) Å ] are also observed.  (1995). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 Table 1 Hydrogen-bond geometry (Å , ).  Benzofurans are found to be useful as anticonvulsant, anti-inflammatory, antitumor, antifungal, anthelmintic and antihyperglycemic agents (Abdel-Aziz et al., 2009;Abdel-Aziz & Mekawey, 2009;Abdel-Wahab et al., 2009;Bhovi et al., 2010). In view of the biological activities and in continuation to our interest with benzofurans, we report herein the crystal structure of the title compound.

Experimental
The title compound was prepared by the reaction of 3-methylbenzofuran-2-carbohydrazide with 2-chloro-1-(4-chlorophenyl)ethanone in absolute ethanol according to the reported method (Abdel-Aziz et al., 2009). Colourless blocks suitable for an X-ray structural analysis were obtained by slow evaporation from EtOH/DMF.
The remaining H atoms were positioned geometrically (C-H = 0.93 and 0.96 Å) and refined with U iso (H) = 1.2 or 1.5U eq (C). A rotating group model was applied to the methyl groups. An outlier, (011), was omitted in the final refinement.

Figure 1
The molecular structure of the title compound with atom labels and 50% probability displacement ellipsoids. The dashed line represents the intramolecular N-H···N hydrogen bond.  The crystal packing of the title compound. The dashed lines represent the hydrogen bonds. For sake of clarity, hydrogen atoms not involved in hydrogen bonding have been omitted.

(N′,N′′Z,N′,N′′E)-N′,N′′-[1-(4-Chlorophenyl)ethane-1,2-diylidene]bis(3methyl-1-benzofuran-2carbohydrazide)
Crystal data  Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.