#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/37/2203715.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_2203715 loop_ _publ_author_name 'Graham Smith' 'Urs D. Wermuth' 'Peter C. Healy' _publ_section_title ; The 1/1/1 adduct hydrate of 8-hydroxy-7-iodoquinoline-5-sulfonic acid (ferron) with urea ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1040 _journal_page_last o1042 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C9 H6 I N O4 S, C H4 N2 O, H2 O' _chemical_formula_moiety 'C9 H6 I N O4 S, C H4 N2 O, H2 O' _chemical_formula_sum 'C10 H12 I N3 O6 S' _chemical_formula_weight 429.19 _chemical_melting_point 502.1--503.3 _chemical_name_common ; 7-iodo-8-hydroxquinoline-5-sulfonic acid--urea--water (1/1/1) ; _chemical_name_systematic ; ; _space_group_IT_number 11 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yb' _symmetry_space_group_name_H-M 'P 1 21/m 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method 'SHELXL-97 (Sheldrick, 1997)' _cell_angle_alpha 90.00 _cell_angle_beta 108.05(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 10.025(3) _cell_length_b 7.335(3) _cell_length_c 9.845(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 16.9 _cell_measurement_theta_min 12.5 _cell_volume 688.3(4) _computing_cell_refinement ; MSC/AFC Diffractometer Control Software ; _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1999) ; _computing_data_reduction ; TEXSAN for Windows (Molecular Structure Corporation, 1999) ; _computing_molecular_graphics 'PLATON for Windows (Spek, 1999)' _computing_publication_material 'PLATON for Windows' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Rigaku rotating anode' _diffrn_measurement_method \w--2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Rigaku AFC-7R' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.0292 _diffrn_reflns_av_sigmaI/netI 0.0215 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 1898 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 2.53 _diffrn_standards_decay_% 1.42 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 2.510 _exptl_absorpt_correction_T_max 0.534 _exptl_absorpt_correction_T_min 0.485 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(TEXSAN for Windows; Molecular Structure Corporation, 1999)' _exptl_crystal_colour 'Yellow ' _exptl_crystal_density_diffrn 2.071 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'Block ' _exptl_crystal_F_000 420 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _refine_diff_density_max 1.163 _refine_diff_density_min -1.338 _refine_ls_extinction_coef 0.115(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 0.891 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 140 _refine_ls_number_reflns 1698 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.891 _refine_ls_R_factor_all 0.0286 _refine_ls_R_factor_gt 0.0274 _refine_ls_shift/su_max 0.0121 _refine_ls_shift/su_mean 0.0033 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.1P)^2^+0.4367P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0849 _refine_ls_wR_factor_ref 0.0868 _reflns_number_gt 1637 _reflns_number_total 1698 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bt6462.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/m' _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '502.1--503.3' was changed to '502.7(6)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2203715 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y+1/2, 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' I I -0.4742 1.8119 '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' N N 0.0061 0.0033 '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' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_type_symbol I7 1.18718(2) 0.250000 0.40545(2) 0.03050(10) Uani 1.000 I S5 0.59432(8) 0.250000 0.15406(8) 0.0195(2) Uani 1.000 S O8 1.0727(3) 0.250000 0.6945(3) 0.0383(9) Uani 1.000 O O51 0.6558(3) 0.250000 0.0395(3) 0.0300(7) Uani 1.000 O O52 0.5141(2) 0.4139(3) 0.16091(19) 0.0299(5) Uani 1.000 O N1 0.8145(3) 0.250000 0.7066(3) 0.0236(8) Uani 1.000 N C2 0.6901(4) 0.250000 0.7238(4) 0.0323(10) Uani 1.000 C C3 0.5689(4) 0.250000 0.6052(4) 0.0397(13) Uani 1.000 C C4 0.5820(4) 0.250000 0.4701(4) 0.0319(10) Uani 1.000 C C5 0.7383(3) 0.250000 0.3150(3) 0.0191(8) Uani 1.000 C C6 0.8731(4) 0.250000 0.3091(3) 0.0217(8) Uani 1.000 C C7 0.9898(3) 0.250000 0.4326(3) 0.0200(8) Uani 1.000 C C8 0.9737(3) 0.250000 0.5674(3) 0.0208(8) Uani 1.000 C C9 0.8336(4) 0.250000 0.5746(3) 0.0202(8) Uani 1.000 C C10 0.7151(3) 0.250000 0.4501(3) 0.0205(8) Uani 1.000 C O21 -0.0156(3) 0.250000 -0.0224(3) 0.0254(7) Uani 1.000 O N11 0.1878(2) 0.4068(3) 0.0289(2) 0.0308(6) Uani 1.000 N C21 0.1157(4) 0.250000 0.0098(3) 0.0229(8) Uani 1.000 C O1W 0.3417(3) 0.250000 0.7870(4) 0.0366(9) Uani 1.000 O H1 0.895(4) 0.250000 0.789(3) 0.038(3) Uiso 1.000 H H2 0.682000 0.250000 0.817700 0.0390 Uiso 1.000 H H3 0.478300 0.250000 0.617800 0.0480 Uiso 1.000 H H4 0.500200 0.250000 0.389800 0.0390 Uiso 1.000 H H6 0.887500 0.250000 0.218200 0.0260 Uiso 1.000 H H8 1.163(7) 0.250000 0.675(6) 0.044(10) Uiso 1.000 H H11A 0.277(3) 0.410(3) 0.044(3) 0.039(4) Uiso 1.000 H H11B 0.133(4) 0.517(5) 0.007(3) 0.036(9) Uiso 1.000 H H1W 0.405(4) 0.330(6) 0.824(4) 0.049(11) Uiso 1.000 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 I7 0.0180(2) 0.0458(2) 0.0292(2) 0.0000 0.00950(10) 0.0000 S5 0.0173(4) 0.0257(4) 0.0127(4) 0.0000 0.0006(3) 0.0000 O8 0.0175(12) 0.077(2) 0.0164(11) 0.0000 -0.0008(10) 0.0000 O51 0.0299(13) 0.0468(14) 0.0123(10) 0.0000 0.0049(9) 0.0000 O52 0.0241(8) 0.0323(8) 0.0282(8) 0.0086(7) 0.0005(7) 0.0012(7) N1 0.0199(14) 0.0393(14) 0.0108(11) 0.0000 0.0038(10) 0.0000 C2 0.0266(19) 0.055(2) 0.0158(15) 0.0000 0.0075(14) 0.0000 C3 0.0175(16) 0.081(3) 0.0224(17) 0.0000 0.0088(14) 0.0000 C4 0.0164(17) 0.061(2) 0.0185(15) 0.0000 0.0056(13) 0.0000 C5 0.0172(15) 0.0252(13) 0.0135(13) 0.0000 0.0028(11) 0.0000 C6 0.0175(15) 0.0313(14) 0.0160(12) 0.0000 0.0046(11) 0.0000 C7 0.0122(14) 0.0310(15) 0.0175(13) 0.0000 0.0057(11) 0.0000 C8 0.0180(15) 0.0288(14) 0.0144(13) 0.0000 0.0034(11) 0.0000 C9 0.0181(14) 0.0285(14) 0.0121(13) 0.0000 0.0017(11) 0.0000 C10 0.0161(14) 0.0280(14) 0.0162(13) 0.0000 0.0034(11) 0.0000 O21 0.0178(13) 0.0334(12) 0.0208(11) 0.0000 0.0000(9) 0.0000 N11 0.0206(10) 0.0299(10) 0.0419(12) -0.0040(8) 0.0095(9) -0.0036(9) C21 0.0219(16) 0.0288(14) 0.0160(13) 0.0000 0.0029(11) 0.0000 O1W 0.0205(14) 0.0383(14) 0.0456(17) 0.0000 0.0023(12) 0.0000 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag I7 C7 2.077(3) no S5 O51 1.443(3) no S5 O52 1.460(2) no S5 C5 1.782(3) no O8 C8 1.335(4) no O8 H8 0.98(7) no O21 C21 1.255(5) no O1W H1W 0.86(4) no N1 C2 1.310(5) no N1 C9 1.371(4) no N1 H1 0.95(3) no N11 C21 1.340(3) no N11 H11A 0.86(3) no N11 H11B 0.96(4) no C2 C3 1.400(6) no C3 C4 1.376(5) no C4 C10 1.408(5) no C5 C10 1.419(4) no C5 C6 1.370(5) no C6 C7 1.402(4) no C7 C8 1.386(4) no C8 C9 1.428(5) no C9 C10 1.418(4) no C2 H2 0.95 no C3 H3 0.95 no C4 H4 0.95 no C6 H6 0.95 no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O51 S5 O52 . . 114.27(10) no O51 S5 C5 . . 105.69(16) no O51 S5 O52 . 4_555 114.27(10) no O52 S5 C5 . . 105.37(10) no O52 S5 O52 . 4_555 110.91(13) no O52 S5 C5 4_555 . 105.37(10) no C8 O8 H8 . . 106(3) no H1W O1W H1W . 4_555 86(4) no C2 N1 C9 . . 122.7(3) no C9 N1 H1 . . 119(2) no C2 N1 H1 . . 119(2) no C21 N11 H11B . . 116(2) no C21 N11 H11A . . 122.3(15) no H11A N11 H11B . . 120(3) no N1 C2 C3 . . 120.5(3) no C2 C3 C4 . . 119.2(4) no C3 C4 C10 . . 120.9(3) no C6 C5 C10 . . 119.3(3) no S5 C5 C10 . . 120.7(2) no S5 C5 C6 . . 120.0(2) no C5 C6 C7 . . 122.1(3) no C6 C7 C8 . . 121.1(3) no I7 C7 C8 . . 121.4(2) no I7 C7 C6 . . 117.4(2) no O8 C8 C7 . . 128.6(3) no C7 C8 C9 . . 117.1(3) no O8 C8 C9 . . 114.2(3) no C8 C9 C10 . . 122.0(3) no N1 C9 C10 . . 119.6(3) no N1 C9 C8 . . 118.4(3) no C4 C10 C9 . . 117.1(3) no C5 C10 C9 . . 118.2(3) no C4 C10 C5 . . 124.7(3) no C3 C2 H2 . . 120 no N1 C2 H2 . . 120 no C2 C3 H3 . . 120 no C4 C3 H3 . . 120 no C3 C4 H4 . . 119 no C10 C4 H4 . . 120 no C5 C6 H6 . . 119 no C7 C6 H6 . . 119 no O21 C21 N11 . 4_555 120.89(18) no N11 C21 N11 . 4_555 118.2(3) no O21 C21 N11 . . 120.89(18) no 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 O51 S5 C5 C6 0.00(2) no O51 S5 C5 C10 180.00(2) no O52 S5 C5 C6 -121.32(10) no O52 S5 C5 C10 58.68(10) no C2 N1 C9 C8 180.00(2) no C9 N1 C2 C3 0.00(2) no C2 N1 C9 C10 0.00(2) no N1 C2 C3 C4 0.00(2) no C2 C3 C4 C10 0.00(2) no C3 C4 C10 C9 0.00(2) no C3 C4 C10 C5 180.00(2) no S5 C5 C6 C7 180.00(2) no C10 C5 C6 C7 0.00(2) no C6 C5 C10 C9 0.00(2) no S5 C5 C10 C9 180.00(2) no C6 C5 C10 C4 180.00(2) no S5 C5 C10 C4 0.00(2) no C5 C6 C7 I7 180.00(2) no C5 C6 C7 C8 0.00(2) no C6 C7 C8 C9 0.00(2) no C6 C7 C8 O8 180.00(2) no I7 C7 C8 O8 0.00(2) no I7 C7 C8 C9 180.00(2) no C7 C8 C9 N1 180.00(2) no O8 C8 C9 C10 180.00(2) no C7 C8 C9 C10 0.00(2) no O8 C8 C9 N1 0.00(2) no N1 C9 C10 C4 0.00(2) no N1 C9 C10 C5 180.00(2) no C8 C9 C10 C4 180.00(2) no C8 C9 C10 C5 0.00(2) no 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 _geom_hbond_publ_flag N1 H1 O8 . 0.95(3) 2.25(3) 2.628(5) 103(2) yes N1 H1 O21 1_656 0.95(3) 1.79(3) 2.684(4) 155(4) yes N1 H1 O21 4_656 0.95(3) 1.79(3) 2.684(4) 155(4) yes O1W H1W O52 3_666 0.86(4) 2.03(4) 2.823(3) 153(4) yes O8 H8 I7 . 0.98(7) 2.74(6) 3.382(3) 124(4) yes O8 H8 O1W 1_655 0.98(7) 1.79(7) 2.565(5) 133(5) yes O8 H8 O1W 4_655 0.98(7) 1.79(7) 2.565(5) 133(5) yes N11 H11A O52 . 0.86(3) 2.30(3) 3.124(3) 161(3) yes C2 H2 O51 1_556 0.95 2.28 3.231(5) 178 yes C4 H4 O52 . 0.95 2.60 3.145(4) 117 yes C4 H4 O52 4_555 0.95 2.60 3.145(4) 117 yes C2 H2 O51 4_556 0.95 2.28 3.231(5) 178 yes C3 H3 O1W . 0.95 2.46 3.304(5) 147 yes C6 H6 O51 . 0.95 2.44 2.865(4) 107 yes