#------------------------------------------------------------------------------ #$Date: 2013-08-29 18:37:19 +0300 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/47/2014721.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2014721 loop_ _publ_author_name 'K. Ravikumar' 'B. Sridhar' _publ_section_title ; Two carbamoyl-substituted dihydropyrimidines: potential mimics of dihydropyridine calcium channel blockers ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o41 _journal_page_last o44 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C13 H14 Cl N3 O S, H2 O' _chemical_formula_moiety 'C13 H14 Cl N3 O S, H2 O' _chemical_formula_sum 'C13 H16 Cl N3 O2 S' _chemical_formula_weight 313.8 _chemical_name_systematic ; 4-(4-chlorophenyl)-6-methyl-5-(N-methylcarbamoyl)-1,2,3,4-dihydropyrimidine- 2-thione monohydrate ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _cell_angle_alpha 79.5060(10) _cell_angle_beta 84.7920(10) _cell_angle_gamma 82.8340(10) _cell_formula_units_Z 2 _cell_length_a 4.8853(3) _cell_length_b 9.7093(7) _cell_length_c 16.0343(11) _cell_measurement_reflns_used 4058 _cell_measurement_temperature 273(2) _cell_measurement_theta_max 29.43 _cell_measurement_theta_min 2.32 _cell_volume 740.18(9) _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_collection 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT (Bruker, 2001)' _computing_molecular_graphics 'Ortep-3 (Farrugia, 1997) and PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 and PARST (Nardelli, 1995)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _diffrn_ambient_temperature 273(2) _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.95 _diffrn_measurement_device 'Bruker SMART APEX CCD area-detector' _diffrn_measurement_device_type 'CCD Area Detector' _diffrn_measurement_method '\w scan' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0228 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 8550 _diffrn_reflns_theta_full 25 _diffrn_reflns_theta_max 27.98 _diffrn_reflns_theta_min 2.15 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.403 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 328 _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.684 _refine_diff_density_min -0.457 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 183 _refine_ls_number_reflns 3391 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.093 _refine_ls_R_factor_all 0.0614 _refine_ls_R_factor_gt 0.0554 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0789P)^2^+0.4380P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1459 _refine_ls_wR_factor_ref 0.1504 _reflns_number_gt 2988 _reflns_number_total 3391 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sk1782.cif _[local]_cod_data_source_block II _cod_depositor_comments ; The following automatic conversions were performed: '_geom_bond_publ_flag' value 'Y' changed to 'y' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (2 times). Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_geom_bond_publ_flag' value 'Y' changed to 'y' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (2 times). Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2014721 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C6 N1 C2 123.36(18) C6 N1 H1 118.3 C2 N1 H1 118.3 C3 C2 N1 118.88(19) C3 C2 C21 127.93(19) N1 C2 C21 113.13(17) C2 C21 H21A 109.5 C2 C21 H21B 109.5 H21A C21 H21B 109.5 C2 C21 H21C 109.5 H21A C21 H21C 109.5 H21B C21 H21C 109.5 C2 C3 C31 124.41(18) C2 C3 C4 120.74(18) C31 C3 C4 114.85(16) O32 C31 N33 122.35(19) O32 C31 C3 120.64(18) N33 C31 C3 116.91(16) C31 N33 C34 122.80(17) C31 N33 H33 118.6 C34 N33 H33 118.6 N33 C34 H34A 109.5 N33 C34 H34B 109.5 H34A C34 H34B 109.5 N33 C34 H34C 109.5 H34A C34 H34C 109.5 H34B C34 H34C 109.5 N5 C4 C3 109.68(16) N5 C4 C7 112.14(17) C3 C4 C7 111.22(16) N5 C4 H4 107.9 C3 C4 H4 107.9 C7 C4 H4 107.9 C6 N5 C4 124.90(18) C6 N5 H5 117.5 C4 N5 H5 117.5 N5 C6 N1 116.97(18) N5 C6 S1 122.10(17) N1 C6 S1 120.92(16) C8 C7 C12 118.3(2) C8 C7 C4 122.56(18) C12 C7 C4 119.13(19) C9 C8 C7 121.1(2) C9 C8 H8 119.4 C7 C8 H8 119.4 C10 C9 C8 119.0(2) C10 C9 H9 120.5 C8 C9 H9 120.5 C11 C10 C9 121.2(2) C11 C10 Cl1 119.2(2) C9 C10 Cl1 119.6(2) C10 C11 C12 119.2(2) C10 C11 H11 120.4 C12 C11 H11 120.4 C11 C12 C7 121.2(2) C11 C12 H12 119.4 C7 C12 H12 119.4 H1W O1W H2W 93.4 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O1W H1W S1 . 0.86 2.47 3.321(3) 177 O1W H2W O1W 2_766 0.86 2.30 2.764(4) 114 N1 H1 S1 2_676 0.86 2.63 3.457(2) 161 N5 H5 O1W 1_455 0.86 2.14 2.990(4) 167 N33 H33 O32 1_655 0.86 2.00 2.824(2) 161 C8 H8 O1W . 0.93 2.55 3.397(4) 151 C21 H21A N(33) . 0.96 2.55 3.116(3) 118 loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag C6 N1 C2 C3 -16.4(3) y C6 N1 C2 C21 160.8(2) ? N1 C2 C3 C31 -178.96(18) ? C21 C2 C3 C31 4.2(3) ? N1 C2 C3 C4 0.8(3) ? C21 C2 C3 C4 -176.0(2) ? C2 C3 C31 O32 -134.9(2) ? C4 C3 C31 O32 45.3(3) ? C2 C3 C31 N33 48.6(3) ? C4 C3 C31 N33 -131.18(19) ? O32 C31 N33 C34 3.6(3) ? C3 C31 N33 C34 -179.9(2) ? C2 C3 C4 N5 17.3(3) y C31 C3 C4 N5 -162.85(16) ? C2 C3 C4 C7 -107.3(2) ? C31 C3 C4 C7 72.5(2) ? C3 C4 N5 C6 -25.1(3) y C7 C4 N5 C6 99.0(2) ? C4 N5 C6 N1 12.6(3) ? C4 N5 C6 S1 -168.37(17) ? C2 N1 C6 N5 9.9(3) y C2 N1 C6 S1 -169.13(16) ? N5 C4 C7 C8 -23.7(3) ? C3 C4 C7 C8 99.5(2) ? N5 C4 C7 C12 158.35(19) ? C3 C4 C7 C12 -78.4(2) ? C12 C7 C8 C9 1.4(3) ? C4 C7 C8 C9 -176.5(2) ? C7 C8 C9 C10 0.1(4) ? C8 C9 C10 C11 -1.4(4) ? C8 C9 C10 Cl1 178.97(19) ? C9 C10 C11 C12 1.1(4) ? Cl1 C10 C11 C12 -179.26(19) ? C10 C11 C12 C7 0.5(4) ? C8 C7 C12 C11 -1.7(4) ? C4 C7 C12 C11 176.3(2) ? _cod_database_fobs_code 2014721