#------------------------------------------------------------------------------ #$Date: 2025-08-19 12:01:59 +0200 (Tue, 19 Aug 2025) $ #$Revision: 301802 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/05/2100558.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_2100558 loop_ _publ_author_name 'C. D. Antoniadis' 'A. J. Blake' 'S. K. Hadjikakou' 'N. Hadjiliadis' 'P. Hubberstey' 'M. Schr\"oder' 'C. Wilson' _publ_section_title ; Structural characterization of selenium and selenium-diiodine analogues of the antithyroid drug 6-n-propyl-2-thiouracil and its alkyl derivatives ; _journal_coeditor_code SO5003 _journal_date_accepted 2006-03-29 _journal_date_recd_electronic 2006-03-08 _journal_issue 4 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 580 _journal_page_last 591 _journal_paper_category FA _journal_paper_doi 10.1107/S0108768106011426 _journal_volume 62 _journal_year 2006 _chemical_formula_moiety 'C24 H26 N8 O4 Se2, 2(H2 O)' _chemical_formula_sum 'C24 H30 N8 O6 Se2' _chemical_formula_weight 684.48 _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method 'enCIFer editing of SHELXL97 CIF output' _cell_angle_alpha 83.490(3) _cell_angle_beta 84.431(3) _cell_angle_gamma 89.353(3) _cell_formula_units_Z 1 _cell_length_a 4.8330(2) _cell_length_b 9.7970(5) _cell_length_c 14.1796(8) _cell_measurement_reflns_used 2951 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 2.9 _cell_volume 663.91(6) _computing_cell_refinement 'DIRAX (Duisenberg, 1992)' _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_data_reduction 'HKL (Otwinowski & Minor, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'enCIFer (Allen et al., 2004); PLATON' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 120(2) _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.980 _diffrn_measurement_device_type 'Bruker Nonius kappaCCD area detector' _diffrn_measurement_method 'omega and phi' _diffrn_radiation_source 'FR591 rotating anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.060 _diffrn_reflns_av_sigmaI/netI 0.091 _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 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 13298 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.71 _diffrn_reflns_theta_min 3.38 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 2.842 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.679 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2003)' _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.712 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 346 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _refine_diff_density_max 3.35 _refine_diff_density_min -2.06 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.04 _refine_ls_hydrogen_treatment 'riding model' _refine_ls_matrix_type full _refine_ls_number_parameters 182 _refine_ls_number_reflns 13281 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.04 _refine_ls_R_factor_all 0.0939 _refine_ls_R_factor_gt 0.0840 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.098P)^2^+8.436P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.214 _refine_ls_wR_factor_ref 0.221 _reflns_number_gt 12058 _reflns_number_total 13281 _reflns_threshold_expression >2sigma(I) _cod_data_source_file so5003.cif _cod_data_source_block 9 _cod_depositor_comments ; Marking attached hydrogen atoms. Antanas Vaitkus, 2017-11-23 The following automatic conversions were performed: '_atom_sites_solution_hydrogens' value 'placed geometrically' was changed to 'geom'. Automatic conversion script Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius ; _cod_database_code 2100558 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_type_symbol _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_attached_hydrogens N N1 0.6706(7) 0.1491(4) 0.6086(3) 0.0261(8) Uani d . 1 0 C C2 0.7861(8) 0.1716(4) 0.5228(3) 0.0213(9) Uani d . 1 0 Se Se2 0.64806(8) 0.05982(4) 0.43430(3) 0.01942(13) Uani d . 1 0 N N3 0.9985(7) 0.2698(4) 0.4937(3) 0.0237(8) Uani d . 1 0 C C4 1.0998(8) 0.3449(4) 0.5642(3) 0.0228(8) Uani d . 1 0 O O4 1.2814(7) 0.4333(4) 0.5408(2) 0.0368(8) Uani d . 1 0 C C5 0.9727(8) 0.3122(5) 0.6585(3) 0.0264(9) Uani d . 1 0 H H5A 1.0339 0.3578 0.7084 0.032 Uiso calc R 1 0 C C6 0.7679(8) 0.2185(4) 0.6795(3) 0.0250(9) Uani d . 1 0 C C7 0.6138(9) 0.1823(5) 0.7756(3) 0.0296(10) Uani d . 1 0 H H7A 0.5975 0.0810 0.7879 0.035 Uiso calc R 1 0 H H7B 0.4233 0.2203 0.7747 0.035 Uiso calc R 1 0 C C8 0.7477(10) 0.2343(5) 0.8576(3) 0.0360(11) Uani d . 1 0 H H8A 0.6346 0.2063 0.9177 0.054 Uiso calc R 1 0 H H8B 0.7601 0.3347 0.8473 0.054 Uiso calc R 1 0 H H8C 0.9347 0.1953 0.8605 0.054 Uiso calc R 1 0 N N11 0.9880(7) 0.2203(4) 0.3389(3) 0.0267(8) Uani d . 1 0 C C12 1.1022(9) 0.2925(5) 0.3959(3) 0.0258(9) Uani d . 1 0 N N13 1.3078(7) 0.3826(4) 0.3670(3) 0.0281(8) Uani d . 1 0 H H13A 1.3749 0.4291 0.4093 0.034 Uiso calc R 1 0 C C14 1.4195(9) 0.4051(4) 0.2715(3) 0.0230(9) Uani d . 1 0 O O14 1.6106(6) 0.4878(3) 0.2466(2) 0.0305(7) Uani d . 1 0 C C15 1.2867(9) 0.3226(5) 0.2087(3) 0.0300(10) Uani d . 1 0 H H15A 1.3446 0.3320 0.1424 0.036 Uiso calc R 1 0 C C16 1.0852(9) 0.2345(5) 0.2442(3) 0.0269(10) Uani d . 1 0 C C17 0.9424(9) 0.1403(5) 0.1876(3) 0.0298(10) Uani d . 1 0 H H17A 0.7429 0.1651 0.1898 0.036 Uiso calc R 1 0 H H17B 0.9554 0.0452 0.2188 0.036 Uiso calc R 1 0 C C18 1.0575(13) 0.1433(6) 0.0841(4) 0.0494(15) Uani d . 1 0 H H18A 0.9521 0.0793 0.0529 0.074 Uiso calc R 1 0 H H18B 1.2535 0.1159 0.0807 0.074 Uiso calc R 1 0 H H18C 1.0411 0.2364 0.0517 0.074 Uiso calc R 1 0 O O1 0.7388(8) 0.5170(5) 0.0441(3) 0.0554(11) Uani d . 1 2 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 N1 0.0294(19) 0.0249(19) 0.025(2) 0.0052(15) -0.0022(15) -0.0069(16) C2 0.022(2) 0.0173(19) 0.025(2) -0.0039(16) 0.0020(17) -0.0099(17) Se2 0.01854(19) 0.01570(19) 0.0238(2) -0.00081(13) -0.00164(15) -0.00138(16) N3 0.0214(17) 0.0253(19) 0.025(2) 0.0008(14) -0.0017(14) -0.0047(16) C4 0.028(2) 0.0216(19) 0.021(2) -0.0046(16) -0.0062(17) -0.0063(18) O4 0.0381(18) 0.043(2) 0.0282(19) -0.0176(16) 0.0025(14) -0.0013(16) C5 0.022(2) 0.032(2) 0.025(2) 0.0013(18) -0.0018(17) -0.0016(19) C6 0.023(2) 0.026(2) 0.026(2) 0.0051(17) -0.0062(17) -0.0043(18) C7 0.028(2) 0.028(2) 0.031(3) -0.0036(19) 0.0029(18) 0.001(2) C8 0.038(3) 0.044(3) 0.024(3) 0.005(2) 0.002(2) 0.001(2) N11 0.0289(19) 0.0242(19) 0.029(2) -0.0042(15) -0.0023(16) -0.0111(16) C12 0.024(2) 0.027(2) 0.025(2) 0.0049(18) -0.0006(17) 0.0030(19) N13 0.030(2) 0.028(2) 0.026(2) 0.0003(16) 0.0026(16) -0.0046(17) C14 0.023(2) 0.022(2) 0.023(2) 0.0028(16) 0.0000(17) -0.0016(18) O14 0.0297(16) 0.0353(18) 0.0252(18) -0.0085(14) 0.0038(13) -0.0031(14) C15 0.030(2) 0.032(2) 0.026(3) 0.0037(19) 0.0032(18) 0.001(2) C16 0.024(2) 0.027(2) 0.031(3) -0.0015(18) -0.0012(18) -0.012(2) C17 0.029(2) 0.029(2) 0.033(3) -0.0024(19) -0.0063(19) -0.006(2) C18 0.085(4) 0.038(3) 0.028(3) -0.010(3) -0.013(3) -0.010(2) O1 0.052(2) 0.078(3) 0.034(2) 0.004(2) 0.0036(17) -0.001(2) 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 0.0000 0.0000 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0929 2.2259 '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_site_symmetry_3 _geom_angle C2 N1 C6 . 119.2(4) N1 C2 N3 . 123.7(4) N1 C2 Se2 . 114.7(3) N3 C2 Se2 . 121.5(3) C2 Se2 Se2 2_656 88.97(13) C2 N3 C12 . 119.4(4) C2 N3 C4 . 118.5(4) C12 N3 C4 . 122.0(4) O4 C4 C5 . 124.5(4) O4 C4 N3 . 120.1(4) C5 C4 N3 . 115.4(4) C6 C5 C4 . 122.1(4) C6 C5 H5A . 119.0 C4 C5 H5A . 119.0 C5 C6 N1 . 121.0(4) C5 C6 C7 . 125.6(4) N1 C6 C7 . 113.3(4) C6 C7 C8 . 114.6(4) C6 C7 H7A . 108.6 C8 C7 H7A . 108.6 C6 C7 H7B . 108.6 C8 C7 H7B . 108.6 H7A C7 H7B . 107.6 C7 C8 H8A . 109.5 C7 C8 H8B . 109.5 H8A C8 H8B . 109.5 C7 C8 H8C . 109.5 H8A C8 H8C . 109.5 H8B C8 H8C . 109.5 C12 N11 C16 . 118.7(4) N11 C12 N13 . 123.6(4) N11 C12 N3 . 116.0(4) N13 C12 N3 . 120.5(4) C12 N13 C14 . 122.0(4) C12 N13 H13A . 119.0 C14 N13 H13A . 119.0 O14 C14 N13 . 120.9(4) O14 C14 C15 . 125.7(4) N13 C14 C15 . 113.3(4) C16 C15 C14 . 120.3(4) C16 C15 H15A . 119.8 C14 C15 H15A . 119.8 C15 C16 N11 . 122.1(4) C15 C16 C17 . 125.1(4) N11 C16 C17 . 112.8(4) C16 C17 C18 . 115.1(4) C16 C17 H17A . 108.5 C18 C17 H17A . 108.5 C16 C17 H17B . 108.5 C18 C17 H17B . 108.5 H17A C17 H17B . 107.5 C17 C18 H18A . 109.5 C17 C18 H18B . 109.5 H18A C18 H18B . 109.5 C17 C18 H18C . 109.5 H18A C18 H18C . 109.5 H18B C18 H18C . 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance N1 C2 . 1.284(5) N1 C6 . 1.396(6) C2 N3 . 1.414(5) C2 Se2 . 1.926(4) Se2 Se2 2_656 2.4328(9) N3 C12 . 1.423(6) N3 C4 . 1.433(5) C4 O4 . 1.235(5) C4 C5 . 1.420(6) C5 C6 . 1.346(6) C5 H5A . 0.9500 C6 C7 . 1.496(6) C7 C8 . 1.522(7) C7 H7A . 0.9900 C7 H7B . 0.9900 C8 H8A . 0.9800 C8 H8B . 0.9800 C8 H8C . 0.9800 N11 C12 . 1.296(6) N11 C16 . 1.371(6) C12 N13 . 1.339(5) N13 C14 . 1.402(5) N13 H13A . 0.8800 C14 O14 . 1.234(5) C14 C15 . 1.464(6) C15 C16 . 1.331(6) C15 H15A . 0.9500 C16 C17 . 1.504(6) C17 C18 . 1.515(7) C17 H17A . 0.9900 C17 H17B . 0.9900 C18 H18A . 0.9800 C18 H18B . 0.9800 C18 H18C . 0.9800 loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139063088