data_2014721 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2005 _journal_volume 61 _journal_page_first o41 _journal_page_last o44 _publ_section_title ; Two carbamoyl-substituted dihydropyrimidines: potential mimics of dihydropyridine calcium channel blockers ; loop_ _publ_author_name 'K. Ravikumar' 'B. Sridhar' _chemical_formula_moiety 'C13 H14 Cl N3 O S, H2 O' _chemical_formula_sum 'C13 H16 Cl N3 O2 S' _chemical_formula_iupac 'C13 H14 Cl N3 O S, H2 O' _chemical_formula_weight 313.8 _symmetry_cell_setting 'triclinic' _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.8853(3) _cell_length_b 9.7093(7) _cell_length_c 16.0343(11) _cell_angle_alpha 79.5060(10) _cell_angle_beta 84.7920(10) _cell_angle_gamma 82.8340(10) _cell_volume 740.18(9) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _exptl_crystal_density_diffrn 1.408 _diffrn_ambient_temperature 273(2) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Cl1 0.75794(19) 0.41129(8) 0.11627(6) 0.0814(3) Uani d . 1 . . Cl S1 0.25270(16) 0.81350(8) 0.53336(4) 0.0596(2) Uani d . 1 . . S N1 0.3387(4) 0.9822(2) 0.38652(11) 0.0434(4) Uani d . 1 . . N H1 0.4623 1.0126 0.4112 0.052 Uiso calc R 1 . . H C2 0.2788(4) 1.0501(2) 0.30423(12) 0.0366(4) Uani d . 1 . . C C3 0.1422(4) 0.9851(2) 0.25714(12) 0.0341(4) Uani d . 1 . . C C4 0.0499(4) 0.8417(2) 0.29214(12) 0.0381(4) Uani d . 1 . . C H4 -0.1418 0.8435 0.2782 0.046 Uiso calc R 1 . . H N5 0.0548(4) 0.8141(2) 0.38475(11) 0.0436(4) Uani d . 1 . . N H5 -0.0528 0.7557 0.4130 0.052 Uiso calc R 1 . . H C6 0.2132(4) 0.8724(2) 0.42864(13) 0.0416(5) Uani d . 1 . . C C7 0.2244(4) 0.7272(2) 0.25137(13) 0.0381(4) Uani d . 1 . . C C8 0.4407(5) 0.6419(2) 0.29067(15) 0.0469(5) Uani d . 1 . . C H8 0.4764 0.6505 0.3454 0.056 Uiso calc R 1 . . H C9 0.6045(6) 0.5440(3) 0.25009(18) 0.0561(6) Uani d . 1 . . C H9 0.7493 0.4870 0.2771 0.067 Uiso calc R 1 . . H C10 0.5499(6) 0.5322(2) 0.16902(16) 0.0530(6) Uani d . 1 . . C C11 0.3337(6) 0.6135(3) 0.12904(15) 0.0552(6) Uani d . 1 . . C H11 0.2972 0.6034 0.0747 0.066 Uiso calc R 1 . . H C12 0.1715(5) 0.7100(3) 0.17028(14) 0.0494(5) Uani d . 1 . . C H12 0.0238 0.7648 0.1435 0.059 Uiso calc R 1 . . H C21 0.3697(5) 1.1941(2) 0.28217(14) 0.0482(5) Uani d . 1 . . C H21A 0.2982 1.2410 0.2293 0.072 Uiso calc R 1 . . H H21B 0.5681 1.1870 0.2768 0.072 Uiso calc R 1 . . H H21C 0.3014 1.2471 0.3262 0.072 Uiso calc R 1 . . H C31 0.0694(4) 1.0440(2) 0.16846(12) 0.0347(4) Uani d . 1 . . C O32 -0.1642(3) 1.03907(19) 0.14632(10) 0.0500(4) Uani d . 1 . . O N33 0.2700(3) 1.0941(2) 0.11453(10) 0.0406(4) Uani d . 1 . . N H33 0.4316 1.0905 0.1326 0.049 Uiso calc R 1 . . H C34 0.2285(5) 1.1544(3) 0.02662(14) 0.0537(6) Uani d . 1 . . C H34A 0.0875 1.1101 0.0070 0.081 Uiso calc R 1 . . H H34B 0.3982 1.1395 -0.0074 0.081 Uiso calc R 1 . . H H34C 0.1724 1.2537 0.0219 0.081 Uiso calc R 1 . . H O1W 0.7517(6) 0.5760(3) 0.4771(2) 0.1086(9) Uani d . 1 . . O H1W 0.6269 0.6372 0.4936 0.080 Uiso d . 1 . . H H2W 0.8231 0.5560 0.5254 0.080 Uiso d . 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl1 0.0999(6) 0.0593(4) 0.0844(6) -0.0026(4) 0.0235(4) -0.0298(4) S1 0.0812(5) 0.0698(4) 0.0302(3) -0.0246(3) -0.0066(3) -0.0026(3) N1 0.0492(10) 0.0541(11) 0.0311(8) -0.0182(8) -0.0069(7) -0.0082(7) C2 0.0361(10) 0.0436(11) 0.0312(9) -0.0061(8) -0.0010(7) -0.0084(8) C21 0.0615(14) 0.0475(12) 0.0396(11) -0.0174(11) -0.0039(10) -0.0106(9) C3 0.0287(9) 0.0421(10) 0.0327(9) -0.0047(7) -0.0013(7) -0.0089(8) C31 0.0288(9) 0.0406(10) 0.0358(10) 0.0007(7) -0.0062(7) -0.0106(8) O32 0.0291(7) 0.0704(11) 0.0519(9) -0.0047(7) -0.0112(6) -0.0104(8) N33 0.0304(8) 0.0590(11) 0.0318(8) -0.0046(7) -0.0066(6) -0.0048(7) C34 0.0542(14) 0.0693(16) 0.0349(11) -0.0045(12) -0.0057(10) -0.0022(10) C4 0.0351(10) 0.0494(12) 0.0327(10) -0.0128(8) -0.0032(7) -0.0084(8) N5 0.0491(10) 0.0528(11) 0.0320(9) -0.0206(8) 0.0034(7) -0.0082(7) C6 0.0447(11) 0.0488(12) 0.0322(10) -0.0072(9) 0.0000(8) -0.0090(8) C7 0.0436(11) 0.0378(10) 0.0348(10) -0.0140(8) -0.0014(8) -0.0057(8) C8 0.0530(13) 0.0487(12) 0.0417(11) -0.0096(10) -0.0086(9) -0.0098(9) C9 0.0604(15) 0.0463(13) 0.0613(15) -0.0025(11) -0.0077(12) -0.0091(11) C10 0.0678(15) 0.0386(11) 0.0539(14) -0.0149(11) 0.0129(12) -0.0136(10) C11 0.0780(17) 0.0532(14) 0.0380(11) -0.0148(12) 0.0003(11) -0.0143(10) C12 0.0606(14) 0.0516(13) 0.0380(11) -0.0058(11) -0.0101(10) -0.0100(9) O1W 0.0989(19) 0.0979(19) 0.120(2) -0.0142(15) -0.0207(17) 0.0125(17) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C10 . 1.742(2) y S1 C6 . 1.693(2) ? N1 C6 . 1.340(3) y N1 C2 . 1.402(3) y N1 H1 . 0.8600 ? C2 C3 . 1.336(3) y C2 C21 . 1.491(3) ? C21 H21A . 0.9600 ? C21 H21B . 0.9600 ? C21 H21C . 0.9600 ? C3 C31 . 1.490(3) ? C3 C4 . 1.510(3) y C31 O32 . 1.235(2) Y C31 N33 . 1.325(3) Y N33 C34 . 1.447(3) ? N33 H33 . 0.8600 ? C34 H34A . 0.9600 ? C34 H34B . 0.9600 ? C34 H34C . 0.9600 ? C4 N5 . 1.462(2) y C4 C7 . 1.522(3) ? C4 H4 . 0.9800 ? N5 C6 . 1.329(3) ? N5 H5 . 0.8600 ? C7 C8 . 1.383(3) ? C7 C12 . 1.392(3) ? C8 C9 . 1.381(3) ? C8 H8 . 0.9300 ? C9 C10 . 1.378(4) ? C9 H9 . 0.9300 ? C10 C11 . 1.371(4) ? C11 C12 . 1.375(3) ? C11 H11 . 0.9300 ? C12 H12 . 0.9300 ? O1W H1W . 0.86 ? O1W H2W . 0.86 ?