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The solid-state structures of three calcium channel antagonists viz. 1,4-dihydro-6-methyl-5-N-methyl-carbamoyl-4-(3′,4′-dichlorophenyl)-2(3 H)-pyrimidinethione, C 13 H 13 N 3 OSCl 2  ( 1 ); 1,4-dihydro-6-methyl-5-N-methyl-carbamoyl-4-(4′-methoxyphenyl)-2(3 H)-pyrimidinethione, C 14 H 17 N 3 O 2 S ( 2 ) and 1,4-dihydro-6-methyl-5-N-methyl-carbamoyl-4-(2′,4′-dichlorophenyl)-2(3 H)-pyrimidineone monohydrate, C 13 H 13 N 3 O 2 Cl 2 ·H 2 O ( 3 ), are reported here. The structures show that these compounds can adopt the important structural features of 1,4-dihydropyridine calcium channel blockers. In ( 2 ), the compound crystallized with three molecules in the asymmetric unit. The dihydropyrimidine ring adopts a half-chair in ( 1 ) and boat conformation in ( 2 ) and ( 3 ). The 4-aryl substituents occupies a pseudo-axial position approximately orthogonal to the plane of the dihydropyrimidine ring [95.1(2)° ( 1 ); 97.5(3)°, 79.8(2)° &amp; 88.2(2)° ( 2 ) and 78.8(3)° ( 3 )]. The C3 substituent, carbamoyl group, is in an extended conformation and oriented anticlinical in ( 1 ) and ( 3 ), but in ( 2 ) two molecules are anticlinal and the other one is synperiplanar, respectively. Intra- and inter- molecular interactions may be influencing the orientation of the C3 carbamoyl group. The 2-chlorophenyl substituent in ( 3 ) is in the axial synperiplanar orientation.

Crystal and molecular structures of 4-aryl-1,4-dihydropyrimidines: Novel calcium channel antagonists