#------------------------------------------------------------------------------ #$Date: 2013-12-28 14:58:47 +0100 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/05/2100552.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_2100552 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 'C5 H6 N2 O Se' _chemical_formula_sum 'C5 H6 N2 O Se' _chemical_formula_weight 189.08 _chemical_name_systematic ; ? ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens 'methyl H atoms from delta-F; others placed geometrically' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method 'enCIFer editing of SHELXL97 CIF output' _cell_angle_alpha 90.00 _cell_angle_beta 90.157(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 4.3411(7) _cell_length_b 14.756(2) _cell_length_c 9.690(2) _cell_measurement_reflns_used 4328 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 29.01 _cell_measurement_theta_min 2.63 _cell_volume 620.71(18) _computing_cell_refinement 'Bruker SAINT (Bruker, 2004)' _computing_data_collection 'Bruker APEX2 (Bruker, 2004)' _computing_data_reduction 'Bruker SAINT' _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 0.924 _diffrn_measured_fraction_theta_max 0.930 _diffrn_measurement_device_type 'Bruker SMART APEXII CCD diffractometer' _diffrn_measurement_method 'fine-slice \w scans' _diffrn_radiation_monochromator 'silicone (111)' _diffrn_radiation_source 'Daresbury Laboratory Station 9.8' _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.6775 _diffrn_reflns_av_R_equivalents 0.027 _diffrn_reflns_av_sigmaI/netI 0.027 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 6350 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 29.01 _diffrn_reflns_theta_min 4.01 _diffrn_standards_decay_% 5 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 5.956 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.816 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS version 2.10; Bruker, 2003)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 2.023 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 368 _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _refine_diff_density_max 0.57 _refine_diff_density_min -0.80 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.803 _refine_ls_hydrogen_treatment 'rigid rotating group; riding model' _refine_ls_matrix_type full _refine_ls_number_parameters 83 _refine_ls_number_reflns 1770 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.803 _refine_ls_R_factor_all 0.0264 _refine_ls_R_factor_gt 0.0246 _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^)+(0.079P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0727 _refine_ls_wR_factor_ref 0.0742 _reflns_number_gt 1642 _reflns_number_total 1770 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file so5003.cif _[local]_cod_data_source_block 1 _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_database_code 2100552 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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_ _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 0.2422(3) 0.73923(8) 0.10993(12) 0.0105(2) Uani d . 1 H H1A 0.3737 0.7485 0.1777 0.013 Uiso calc R 1 C C2 0.1605(3) 0.65292(9) 0.08020(14) 0.0104(2) Uani d . 1 Se Se2 0.32333(3) 0.556089(10) 0.173603(14) 0.01181(9) Uani d . 1 N N3 -0.0470(3) 0.64228(8) -0.02297(12) 0.0116(2) Uani d . 1 H H3A -0.1048 0.5866 -0.0428 0.014 Uiso calc R 1 C C4 -0.1767(3) 0.71205(9) -0.10027(15) 0.0119(3) Uani d . 1 O O4 -0.3644(3) 0.69250(9) -0.19136(13) 0.0180(2) Uani d . 1 C C5 -0.0765(3) 0.80120(9) -0.06473(15) 0.0119(2) Uani d . 1 H H5A -0.1540 0.8521 -0.1139 0.014 Uiso calc R 1 C C6 0.1301(3) 0.81340(9) 0.03956(14) 0.0111(2) Uani d . 1 C C7 0.2429(3) 0.90396(9) 0.08536(16) 0.0153(3) Uani d . 1 H H7D 0.2201 0.9475 0.0097 0.023 Uiso calc R 1 H H7A 0.4606 0.8995 0.1116 0.023 Uiso calc R 1 H H7B 0.1223 0.9243 0.1648 0.023 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 0.0136(5) 0.0082(5) 0.0097(5) -0.0003(4) -0.0031(4) -0.0010(4) C2 0.0119(5) 0.0100(6) 0.0093(6) 0.0011(4) -0.0006(4) 0.0007(4) Se2 0.01526(13) 0.00869(12) 0.01146(12) 0.00109(4) -0.00368(7) 0.00126(4) N3 0.0137(5) 0.0089(5) 0.0123(5) -0.0014(4) -0.0043(4) 0.0003(4) C4 0.0126(6) 0.0115(6) 0.0116(6) 0.0009(5) -0.0018(5) 0.0011(5) O4 0.0203(5) 0.0170(6) 0.0165(5) -0.0005(4) -0.0106(4) 0.0005(4) C5 0.0140(6) 0.0100(6) 0.0116(6) 0.0008(5) -0.0032(5) 0.0014(5) C6 0.0135(6) 0.0089(6) 0.0108(6) 0.0005(4) -0.0005(5) -0.0001(4) C7 0.0198(7) 0.0093(6) 0.0169(7) -0.0004(5) -0.0052(5) -0.0013(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C2 1.3528(17) N1 C6 1.3776(17) N1 H1A 0.8800 C2 N3 1.3531(18) C2 Se2 1.8322(14) N3 C4 1.3913(18) N3 H3A 0.8800 C4 O4 1.2338(18) C4 C5 1.427(2) C5 C6 1.361(2) C5 H5A 0.9500 C6 C7 1.4904(19) C7 H7D 0.9800 C7 H7A 0.9800 C7 H7B 0.9800 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 N1 C6 123.40(12) C2 N1 H1A 118.3 C6 N1 H1A 118.3 N1 C2 N3 116.12(12) N1 C2 Se2 121.90(10) N3 C2 Se2 121.98(10) C2 N3 C4 125.41(12) C2 N3 H3A 117.3 C4 N3 H3A 117.3 O4 C4 N3 118.52(13) O4 C4 C5 126.04(14) N3 C4 C5 115.44(13) C6 C5 C4 120.05(13) C6 C5 H5A 120.0 C4 C5 H5A 120.0 C5 C6 N1 119.57(12) C5 C6 C7 123.70(13) N1 C6 C7 116.72(12) C6 C7 H7D 109.5 C6 C7 H7A 109.5 H7D C7 H7A 109.5 C6 C7 H7B 109.5 H7D C7 H7B 109.5 H7A C7 H7B 109.5 _journal_paper_doi 10.1107/S0108768106011426