All the compounds were identified by spectral data. In general, mass spectrum showed the molecular
ion peak, which corresponds to the formula weight of the hydrazones. The elemental analyses of the compounds are in consistence with the molecular formula (Table 1). The electronic spectra of the hydrazones A1–A6 were taken in ethanol (10−3 mol−1). In the UV–Visible spectra of all these compounds the first band appeared around 257 nm was due to the π → π* transitions of the heterocyclic ring and the second one appeared around 350 nm was due to the n → π* transition of the >C]N–group. 8 FT-IR spectra showed the C]O peak around 1660 cm−1, C=N around 1560 cm−1 and the NH stretching vibrations around Compound C 3064 cm−1. The 1H NMR spectrum showed the hydrazide (NH) protons as a singlet around 12.1 ppm, the imine protons (N]C–H) around 8.3 ppm, methoxy protons around 3.8 ppm and aromatic protons in the range 6.5–8.8. The 13C NMR spectrum showed the C]O signals around 162.5, C]N signals around 150.6 ppm, Talazoparib research buy OCH3 signals around 55.5 ppm and aromatic carbon in the range 114.7–158.5 ppm. 9 Single crystals suitable for X-ray diffraction study for the hydrazone (A1) was grown from the slow evaporation of an ethanol solution at room
temperature. A pale yellow crystal of (A1) was mounted on a glass fiber and used for data collection. Crystal data was collected using graphite monochromatised Mo-Kα radiation (λ = 0.71073 Å). The structure was solved by direct method using SHELEX-97 and refined by full-matrix least-squares techniques against F2 using SHELEX-97. All the non-hydrogen atoms were refined anisotropically. A summary of pertinent crystal data along with further details of structure determination and refinement are given in Table 2. Selected bond lengths and bond angles are given in Table 3.The hydrazone crystallizes in an orthorhombic, chiral space group pbca. The single crystal
X-ray structure of A1 reveals the presence of two molecules in the unit cell. The C]N azomethine [N(3)–C(7)]-bond length 1.278 (3) Å in A1 has a double bond character. The existence of A1 in keto Linifanib (ABT-869) form in solid state is evident from the [O(1)–C(6)] bond length 1.223 (3) Å and the side chain carbonyl [O(1)-C(6)] show a typical double bond character with bond length 1.223 (3) Å.10 and 11 In this compound, there is also an intermolecular hydrogen bond (Table 4) between the N(2)–H(4) and N(1)′ [N(2)–H(4)…N(1)′, 2.225 Å] and N(2)′–H(5) and N(1) [N(2)′–H(5)…N(1), 2.202 Å], stabilize the crystal structure forming a supramolecular architecture. ORTEP view and unit cell of A1 are given in Fig. 1 and Fig. 2 respectively.