[C:1]1([C:7]2[S:11][C:10]([O:12][C@@H:13]3[CH:20]4[CH2:21][N:16]5[CH2:17][CH:18]([CH2:22][CH:14]3[CH2:15]5)[CH2:19]4)=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:23]([OH:35])(=[O:34])[CH2:24][C:25]([CH2:30][C:31]([OH:33])=[O:32])([C:27]([OH:29])=[O:28])[OH:26]>CO>[C:23]([OH:35])(=[O:34])[CH2:24][C:25]([CH2:30][C:31]([OH:33])=[O:32])([C:27]([OH:29])=[O:28])[OH:26].[C:1]1([C:7]2[S:11][C:10]([O:12][C@@H:13]3[CH:20]4[CH2:21][N:16]5[CH2:17][CH:18]([CH2:22][CH:14]3[CH2:15]5)[CH2:19]4)=[N:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1(4s)-4-(5-Phenyl-1,3,4-thiadiazol-2-yloxy)-1-azatricyclo[3.3.1.13,7]decane free base (62 mg, 0.2 mmol) was dissolved in 1.5 mL of methanol. Citric acid (19 mg, 0.1 mmol) was dissolved in 0.5 mL of methanol. The citric acid solution was added to the (4s)-4-(5-phenyl-1,3,4-thiadiazol-2-yloxy)-1-azatricyclo[3.3.1.13,7]decane free base solution while stirring. (4s)-4-(5-Phenyl-1,3,4-thiadiazol-2-yloxy)-1-azatricyclo[3.3.1.13,7]decane monohydrogen citrate crystallized over time while stirring.
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