(1Z,2E)-N′-{1-[2-(4-Bromophenyl)hydrazin-1-ylidene]-1-chloropropan-2-ylidene}thiophene-2-carbohydrazide

In the title compound, C14H12BrClN4OS, the thienyl ring is disordered over two orientations with a site-occupancy ratio of 0.853 (2):0.147 (2). The molecule is roughly planar, with the dihedral angles between the thienyl and benzene rings being 6.24 (16) and 9.7 (11)° for the major and minor components, respectively. The central fragment is almost planar [r.m.s. deviation = 0.0275 (2) Å for the ten non-H atoms]. The mean plane through this middle unit makes a dihedral angle of 2.71 (7)° with the benzene ring, whereas these values are 4.46 (15) and 7.7 (11)° for the major and minor components of the thienyl ring, respectively. In the crystal, molecules are linked into dimers by pairs of N—H⋯O hydrogen bonds, forming R 2 2(8) ring motifs. These dimers are arranged into sheets parallel to the ac plane.

In the title compound, C 14 H 12 BrClN 4 OS, the thienyl ring is disordered over two orientations with a site-occupancy ratio of 0.853 (2):0.147 (2). The molecule is roughly planar, with the dihedral angles between the thienyl and benzene rings being 6.24 (16) and 9.7 (11) for the major and minor components, respectively. The central fragment is almost planar [r.m.s. deviation = 0.0275 (2) Å for the ten non-H atoms]. The mean plane through this middle unit makes a dihedral angle of 2.71 (7) with the benzene ring, whereas these values are 4.46 (15) and 7.7 (11) for the major and minor components of the thienyl ring, respectively. In the crystal, molecules are linked into dimers by pairs of N-HÁ Á ÁO hydrogen bonds, forming R 2 2 (8) ring motifs. These dimers are arranged into sheets parallel to the ac plane.
In the crystal packing ( Fig. 2), the molecules are linked into dimers by pairs of N-H···O hydrogen bonds forming the R 2 2 (8) ring motifs (Bernstein et al., 1995) and these dimers arranged into sheets parallel to the ac plane.

Experimental
A mixture of thiophene-2-carbohydrazide (1.42 g, 10 mmol) and (Z)-N′-(4-bromophenyl)-2-oxopropanehydrazonoyl chloride (2.76 g, 10 mmol) in absolute ethanol (50 ml) was refluxed for 6 h. The reaction was then left to cool at room temperature. The solid formed was filtered off, washed with ethanol and recrystallized twice from EtOH to afford yellow needle-shaped title compound.

Refinement
Amide H atom was located in Fourier difference maps and refined isotrpically. The remainning H atoms were positioned geometrically and allowed to ride on their parent atoms, with d(C-H) = 0.93 Å for aromatic and 0.96 Å for CH 3 atoms.
The U iso values were constrained to be 1.5U eq of the carrier atom for methyl H atoms and 1.2U eq for the remaining H atoms. A rotating group model was used for the methyl groups. The thiophene ring is disordered over two sites in a 0.853 (2): 0.147 (2) occupancy ratio. Similarity restraint were used for the disordered thienyl ring. The thermal ellipsoids of each of the two pairs of atoms [C12X and C14X as well as S1X and C13X] were restrained to be the same.

Figure 1
The molecular structure of the title compound with 50% probability displacement ellipsoids and the atom-numbering scheme. Open bonds show the minor component. The crystal packing of the title compound viewed along the b axis. Hydrogen bonds were shown as dash lines.  (Cosier & Glazer, 1986) operating at 100.0 (1) K. Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. 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 > 2sigma(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq Occ. (