In this study, a novel 4-((4-chlorophenylsulfonamido)methyl)cyclohexanecarboxylic acid(C_(14)H_(18)ClNO_4S) was synthesized by the reaction of tranexamic acid and 4-chlororbenzene sulfonyl chloride in basic medium at room temperature. The molecular structure was determined by FT-IR, NMR, elemental analysis and single-crystal X-ray analysis. The compound crystallizes in the monoclinic system, space group P21/c with a = 12.3120(11), b = 16.5987(19), c = 7.6873(7) ?, β = 90.495(6)o, Z = 4 and V = 1570.9(3) ?~3, crystal size(mm) = 0.38 × 0.16 × 0.14 and Rint = 0.045. In this compound, the carboxylic acid A(O(1)/C(1)/C(2)) and the sulfonyl B(O(3)/S(1)/O(4)) moieties are of course planar. The molecules are dimerized due to the O–H···O type of H-bonding with the R_2~2(8) ring motifs. The dimmers are interlinked through C–H···O and N–H···O types of H-bonding. The synthesized compound was screened against four bacterial and two fungal strains and inactive against all strains. Antioxidant activity was checked against DPPH. Enzyme inhibition activity was carried out using three different enzymes and the title compound was more potent α-chymotrypsin inhibitor. In this study, a novel 4 - (4-chlorophenylsulfonamido) methyl) cyclohexanecarboxylic acid (C_ (14) H_ (18) ClNO_4S) was synthesized by the reaction of tranexamic acid and 4-chlororbenzene sulfonyl chloride in basic medium at room temperature The molecular structure was determined by FT-IR, NMR, elemental analysis and single-crystal X-ray analysis. The compound crystallizes in the monoclinic system, space group P21 / c with a = 12.3120 (11), b = 16.5987 , c = 7.6873 (7), β = 90.495 (6) o, Z = 4 and V = 1570.9 (3) ~ 3, crystal size (mm) = 0.38 × 0.16 × 0.14 and Rint = 0.045. , the carboxylic acid A (O (1) / C (1) / C (2)) and the sulfonyl B (O (3) / S (1) / O (4)) moieties are of course planar. The molecules are dimerized due to the O-H ··· O type of H-bonding with the R_2 ~ 2 (8) ring motifs. The dimmers are interlinked through C-H ··· O and N-H · O types of H -bonding. The synthesized compound was screened against four bacterial and two fungal strains and inactive against all strains. Antioxidant activity was checked against DPPH. Enzyme inhibition activity was carried out using three different enzymes and the title compound was more potent α-chymotrypsin inhibitor.