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The crystal structures of four acylhydrazonyl derivatives of thiophene, 2-(ArCH = N–NHCO)- thiophene, ( 1a),  2-(ArCH = N–NMeCO)-thiophene, ( 2a ), 2-(ArCH = N–NHCOCH 2 )-thiophene, ( 3a ) and 2-(ArCH =  N–NMeCOCH 2 )-thiophene, ( 4a ) [in each case Ar =  5-nitrothien-2-yl] are reported. The molecular conformations of  1a  and  2a  are near planar, while those of  3a  and  4a  exhibit bends at the methylene carbon. Methylations at the hydrazonyl groups in  1a  and  3a , to give  2a  and  4a,  do not result in any significant changes in the molecular conformations. Each of the four molecular conformations possesses a  Z  C(O)NR / E   (C  =  N)   arrangement about the C(O)–NR–N = C(H, aryl) fragment (R = H or Me). The dominant intermolecular interactions in  1a  and  3a  are N–H···O(carbonyl) hydrogen bonds, with other intermolecular interactions being weaker interactions: C–H···O and N–O···π in  1a  and C–H···X (X = O, S, π) and π–π interactions in  3a . In the  N -methylated compounds, the intermolecular interactions are restricted to weaker C–H···O hydrogen bonds in  2a  and C–H···X (X = O or π) interactions in  4a .

Crystal structures of 2-[5-nitrothien-2-yl)- CH=N–NR–CO(CH 2 ) n ]thiophene compounds (R = H or Me; n = 0 or 1)