#------------------------------------------------------------------------------ #$Date: 2012-02-03 18:16:24 +0100 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/05/2100559.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_2100559 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_volume 62 _journal_year 2006 _chemical_formula_moiety 'C28 H34 N8 O4 Se2' _chemical_formula_sum 'C28 H34 N8 O4 Se2' _chemical_formula_weight 704.55 _chemical_name_systematic ; ? ; _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 83.161(2) _cell_angle_beta 82.785(2) _cell_angle_gamma 84.358(2) _cell_formula_units_Z 1 _cell_length_a 5.0717(6) _cell_length_b 11.8615(14) _cell_length_c 11.9385(14) _cell_measurement_reflns_used 1672 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.03 _cell_measurement_theta_min 2.20 _cell_volume 704.90(14) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'enCIFer (Allen et al., 2004); PLATON' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 120(2) _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.975 _diffrn_measurement_device_type 'Bruker SMART APEXII CCD diffractometer' _diffrn_measurement_method 'fine-slice \w scans' _diffrn_radiation_monochromator 'silicon 111' _diffrn_radiation_source 'Daresbury Laboratory Station 9.8' _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.6775 _diffrn_reflns_av_R_equivalents 0.038 _diffrn_reflns_av_sigmaI/netI 0.067 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 8292 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 28.94 _diffrn_reflns_theta_min 2.21 _diffrn_standards_decay_% 5 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 2.674 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.804 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS version 2.10; Bruker, 2003)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.660 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 358 _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.01 _refine_diff_density_max 0.59 _refine_diff_density_min -0.92 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.98 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 190 _refine_ls_number_reflns 4198 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.98 _refine_ls_R_factor_all 0.0702 _refine_ls_R_factor_gt 0.0415 _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^)+(0.0505P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0859 _refine_ls_wR_factor_ref 0.0968 _reflns_number_gt 3144 _reflns_number_total 4198 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file so5003.cif _[local]_cod_data_source_block 10 _cod_database_code 2100559 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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_ _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 N N1 0.0981(5) -0.0445(2) 0.1979(2) 0.0214(5) Uani d . 1 C C2 0.2181(6) 0.0405(2) 0.1429(3) 0.0210(6) Uani d . 1 Se Se2 0.14052(6) 0.07943(3) -0.01112(3) 0.01897(9) Uani d . 1 N N3 0.3931(5) 0.1001(2) 0.1918(2) 0.0194(5) Uani d . 1 C C4 0.4500(6) 0.0647(3) 0.3048(2) 0.0236(6) Uani d . 1 O O4 0.6093(5) 0.1120(2) 0.34994(19) 0.0314(5) Uani d . 1 C C5 0.3102(6) -0.0281(3) 0.3613(3) 0.0245(6) Uani d . 1 H H5A 0.3359 -0.0544 0.4378 0.029 Uiso calc R 1 C C6 0.1422(5) -0.0795(2) 0.3089(3) 0.0209(6) Uani d . 1 C C7 -0.0107(6) -0.1780(3) 0.3649(3) 0.0236(6) Uani d . 1 H H7A 0.0355 -0.2433 0.3195 0.028 Uiso calc R 1 H H7B -0.2039 -0.1558 0.3640 0.028 Uiso calc R 1 C C8 0.0425(6) -0.2165(3) 0.4867(3) 0.0255(6) Uani d . 1 H H8A -0.0072 -0.1521 0.5329 0.031 Uiso calc R 1 H H8B 0.2357 -0.2381 0.4882 0.031 Uiso calc R 1 C C9 -0.1119(7) -0.3171(3) 0.5394(3) 0.0313(7) Uani d . 1 H H9A -0.0665 -0.3402 0.6167 0.047 Uiso calc R 1 H H9B -0.0650 -0.3810 0.4936 0.047 Uiso calc R 1 H H9C -0.3037 -0.2950 0.5419 0.047 Uiso calc R 1 N N11 0.4481(5) 0.2217(2) 0.0257(2) 0.0227(5) Uani d . 1 C C12 0.5138(6) 0.1946(3) 0.1253(3) 0.0216(6) Uani d . 1 N N13 0.6875(5) 0.2497(2) 0.1721(2) 0.0247(5) Uani d . 1 H H13A 0.7181 0.2278 0.2427 0.030 Uiso calc R 1 C C14 0.8191(6) 0.3401(3) 0.1118(3) 0.0232(6) Uani d . 1 O O14 0.9837(4) 0.3836(2) 0.15667(19) 0.0316(5) Uani d . 1 C C15 0.7378(6) 0.3730(3) 0.0002(3) 0.0241(6) Uani d . 1 H H15A 0.8101 0.4360 -0.0461 0.029 Uiso calc R 1 C C16 0.5581(6) 0.3141(3) -0.0391(3) 0.0232(6) Uani d . 1 C C17 0.4620(6) 0.3411(3) -0.1530(3) 0.0260(6) Uani d . 1 H H17B 0.2678 0.3628 -0.1416 0.031 Uiso calc R 1 H H17A 0.4877 0.2705 -0.1912 0.031 Uiso calc R 1 C C18 0.5926(6) 0.4350(3) -0.2332(3) 0.0265(6) Uani d . 1 H H18A 0.7797 0.4135 -0.2494 0.032 Uiso calc R 1 H H18B 0.5728 0.5040 -0.1973 0.032 Uiso calc R 1 C C19 0.4659(7) 0.4554(3) -0.3430(3) 0.0365(8) Uani d . 1 H H19A 0.5535 0.5152 -0.3938 0.055 Uiso calc R 1 H H19B 0.2758 0.4793 -0.3266 0.055 Uiso calc R 1 H H19C 0.4864 0.3848 -0.3796 0.055 Uiso calc R 1 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 0.0211(12) 0.0241(13) 0.0209(13) -0.0053(9) -0.0078(10) -0.0021(10) C2 0.0197(13) 0.0227(15) 0.0232(15) -0.0029(10) -0.0088(11) -0.0063(12) Se2 0.01838(14) 0.02263(15) 0.01808(14) -0.00510(9) -0.00676(9) -0.00343(10) N3 0.0212(12) 0.0220(12) 0.0175(12) -0.0067(9) -0.0071(9) -0.0033(10) C4 0.0268(15) 0.0265(16) 0.0191(15) -0.0048(12) -0.0062(12) -0.0026(12) O4 0.0373(13) 0.0372(13) 0.0244(12) -0.0172(10) -0.0145(10) 0.0004(10) C5 0.0273(15) 0.0255(15) 0.0219(15) -0.0055(11) -0.0085(12) 0.0008(12) C6 0.0194(13) 0.0223(14) 0.0219(14) -0.0011(10) -0.0057(11) -0.0035(11) C7 0.0246(15) 0.0243(15) 0.0234(15) -0.0061(11) -0.0079(12) -0.0002(12) C8 0.0286(15) 0.0267(15) 0.0225(15) -0.0069(12) -0.0075(12) 0.0011(12) C9 0.0329(17) 0.0331(18) 0.0293(17) -0.0108(13) -0.0082(13) 0.0027(14) N11 0.0263(13) 0.0252(13) 0.0190(12) -0.0076(10) -0.0088(10) -0.0010(10) C12 0.0214(14) 0.0211(14) 0.0241(15) -0.0047(11) -0.0041(11) -0.0053(12) N13 0.0257(13) 0.0307(14) 0.0194(13) -0.0083(10) -0.0068(10) -0.0009(11) C14 0.0236(15) 0.0258(15) 0.0229(15) -0.0075(11) -0.0048(12) -0.0067(12) O14 0.0335(12) 0.0375(13) 0.0282(12) -0.0185(10) -0.0093(10) -0.0026(10) C15 0.0223(14) 0.0232(15) 0.0279(16) -0.0075(11) -0.0032(12) -0.0026(13) C16 0.0201(14) 0.0243(15) 0.0258(15) -0.0036(11) -0.0043(11) -0.0024(12) C17 0.0244(15) 0.0321(17) 0.0229(15) -0.0094(12) -0.0034(12) -0.0017(13) C18 0.0283(16) 0.0278(16) 0.0240(16) -0.0076(12) -0.0043(12) -0.0002(13) C19 0.046(2) 0.039(2) 0.0265(17) -0.0169(16) -0.0099(15) 0.0041(15) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance N1 C2 . 1.296(4) N1 C6 . 1.379(4) C2 N3 . 1.407(3) C2 Se2 . 1.921(3) Se2 Se2 2 2.4427(6) N3 C4 . 1.421(4) N3 C12 . 1.437(4) C4 O4 . 1.236(3) C4 C5 . 1.423(4) C5 C6 . 1.348(4) C5 H5A . 0.9500 C6 C7 . 1.509(4) C7 C8 . 1.520(4) C7 H7A . 0.9900 C7 H7B . 0.9900 C8 C9 . 1.522(4) C8 H8A . 0.9900 C8 H8B . 0.9900 C9 H9A . 0.9800 C9 H9B . 0.9800 C9 H9C . 0.9800 N11 C12 . 1.272(4) N11 C16 . 1.386(4) C12 N13 . 1.356(3) N13 C14 . 1.396(4) N13 H13A . 0.8800 C14 O14 . 1.230(3) C14 C15 . 1.443(4) C15 C16 . 1.360(4) C15 H15A . 0.9500 C16 C17 . 1.491(4) C17 C18 . 1.526(4) C17 H17B . 0.9900 C17 H17A . 0.9900 C18 C19 . 1.515(4) C18 H18A . 0.96 C18 H18B . 0.96 C19 H19A . 0.9800 C19 H19B . 0.9800 C19 H19C . 0.9800 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 . 119.6(2) N1 C2 N3 . 122.6(3) N1 C2 Se2 . 115.2(2) N3 C2 Se2 . 122.2(2) C2 Se2 Se2 2 89.43(9) C2 N3 C4 . 119.6(2) C2 N3 C12 . 119.0(2) C4 N3 C12 . 121.4(2) O4 C4 N3 . 121.9(3) O4 C4 C5 . 123.0(3) N3 C4 C5 . 115.1(2) C6 C5 C4 . 121.6(3) C6 C5 H5A . 119.2 C4 C5 H5A . 119.2 C5 C6 N1 . 121.4(3) C5 C6 C7 . 123.7(3) N1 C6 C7 . 114.9(2) C6 C7 C8 . 114.3(2) C6 C7 H7A . 108.7 C8 C7 H7A . 108.7 C6 C7 H7B . 108.7 C8 C7 H7B . 108.7 H7A C7 H7B . 107.6 C7 C8 C9 . 112.6(2) C7 C8 H8A . 109.1 C9 C8 H8A . 109.1 C7 C8 H8B . 109.1 C9 C8 H8B . 109.1 H8A C8 H8B . 107.8 C8 C9 H9A . 109.5 C8 C9 H9B . 109.5 H9A C9 H9B . 109.5 C8 C9 H9C . 109.5 H9A C9 H9C . 109.5 H9B C9 H9C . 109.5 C12 N11 C16 . 118.2(2) N11 C12 N13 . 124.1(3) N11 C12 N3 . 117.2(2) N13 C12 N3 . 118.6(3) C12 N13 C14 . 122.1(3) C12 N13 H13A . 119.0 C14 N13 H13A . 119.0 O14 C14 N13 . 119.3(3) O14 C14 C15 . 127.1(3) N13 C14 C15 . 113.6(2) C16 C15 C14 . 120.2(3) C16 C15 H15A . 119.9 C14 C15 H15A . 119.9 C15 C16 N11 . 121.7(3) C15 C16 C17 . 124.3(3) N11 C16 C17 . 114.0(2) C16 C17 C18 . 117.0(2) C16 C17 H17B . 108.1 C18 C17 H17B . 108.1 C16 C17 H17A . 108.1 C18 C17 H17A . 108.1 H17B C17 H17A . 107.3 C19 C18 C17 . 110.5(3) C19 C18 H18A . 111 C17 C18 H18A . 110 C19 C18 H18B . 110 C17 C18 H18B . 109 H18A C18 H18B . 108 C18 C19 H19A . 109.5 C18 C19 H19B . 109.5 H19A C19 H19B . 109.5 C18 C19 H19C . 109.5 H19A C19 H19C . 109.5 H19B C19 H19C . 109.5