The need in safe and highly effective analgesic medications to prevent and treat acute and chronic pains is accompanied by search of antidepressants and anxiolytics to suppress the convoyed depression, anxiety and insomnia. Among the 3-substituted 1,4-benzodiazepine-2-ones analgesic activity exhibit antagonists of bradykinin, a powerful natural algogen [1,2].We have synthesized 1-methoxycarbonylmethyl-3-arylamino-1,2-dihydro-3Н-1,4-benzdiazepine-2-ones IVI and disclosed their high analgesic activity.schemeThe structures of I, III, IV and VI were confirmed by single crystal X-ray diffraction. In the molecules with o-position of NO2 (I) or COOCH3 (IV) group in arylamino fragment only the intramolecular H-bond was found, while in the cases with p-position of these groups (III, VI) the molecules associate in centrosym metric dimers via a couple of N-H···O (III) and N-H···N(VI) hydrogen bonds. The further aggregation of molecules in crystals is achieved via stacking interactions and weak hydrogen bonds including CH···Br, and CH···O contacts acting through the different association patterns and combining the molecules in different packing motifs.