#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/51/2205186.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_2205186 loop_ _publ_author_name 'Fan, Sai-Rong' 'Xiao, Hong-Ping' 'Zhu, Long-Guan' _publ_section_title ; A cation--anion complex: 1,10-phenanthrolin-1-ium 5-sulfonatosalicylic acid ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o253 _journal_page_last o255 _journal_paper_doi 10.1107/S1600536804034245 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C12 H9 N2 +, C7 H5 O6 S -' _chemical_formula_moiety 'C12 H9 N2 +, C7 H5 O6 S -' _chemical_formula_sum 'C19 H14 N2 O6 S' _chemical_formula_weight 398.38 _chemical_name_systematic ; 1,10-phenanthrolin-1-ium 5-sulfosalicylate ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 103.426(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 7.0492(9) _cell_length_b 10.6716(14) _cell_length_c 11.7464(15) _cell_measurement_reflns_used 5405 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 28.3 _cell_measurement_theta_min 0.9 _cell_volume 859.49(19) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1997)' _computing_data_reduction 'SAINT and? SHELXTL (Bruker, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 295(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w scans' _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 0.0136 _diffrn_reflns_av_sigmaI/netI 0.0283 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 4555 _diffrn_reflns_theta_full 25.15 _diffrn_reflns_theta_max 25.15 _diffrn_reflns_theta_min 2.61 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.231 _exptl_absorpt_correction_T_max 0.9641 _exptl_absorpt_correction_T_min 0.9255 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.539 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 412 _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.262 _refine_diff_density_min -0.327 _refine_ls_abs_structure_details 'Flack (1983), 1312 Friedel pairs?' _refine_ls_abs_structure_Flack 0.04(9) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.180 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 262 _refine_ls_number_reflns 2938 _refine_ls_number_restraints 4 _refine_ls_restrained_S_all 1.179 _refine_ls_R_factor_all 0.0433 _refine_ls_R_factor_gt 0.0429 _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^)+(0.0565P)^2^+0.1823P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1057 _refine_ls_wR_factor_ref 0.1060 _reflns_number_gt 2910 _reflns_number_total 2938 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ww6336.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 2205186 _cod_database_fobs_code 2205186 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -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_type_symbol S1 0.69901(10) 0.84471(7) 0.22996(5) 0.03425(18) Uani d . 1 S O1 0.9358(4) 0.5001(2) 0.54499(18) 0.0535(6) Uani d D 1 O O2 0.9153(4) 0.3121(2) 0.4606(2) 0.0592(7) Uani d . 1 O O3 0.8106(4) 0.2968(2) 0.2349(2) 0.0567(7) Uani d D 1 O O4 0.5887(3) 0.8750(2) 0.11248(18) 0.0466(6) Uani d . 1 O O5 0.8936(3) 0.9012(2) 0.25274(19) 0.0473(6) Uani d . 1 O O6 0.5978(4) 0.8708(2) 0.32056(19) 0.0552(6) Uani d . 1 O C1 0.8951(4) 0.4252(3) 0.4547(3) 0.0388(7) Uani d . 1 C C2 0.8235(4) 0.4901(3) 0.3418(2) 0.0342(6) Uani d . 1 C C3 0.7858(5) 0.4216(3) 0.2368(3) 0.0389(7) Uani d . 1 C C4 0.7206(4) 0.4844(3) 0.1305(3) 0.0415(7) Uani d . 1 C H4 0.6937 0.4394 0.0609 0.050 Uiso calc R 1 H C5 0.6958(4) 0.6124(3) 0.1280(2) 0.0353(6) Uani d . 1 C H5 0.6537 0.6535 0.0568 0.042 Uiso calc R 1 H C6 0.7336(4) 0.6798(3) 0.2315(2) 0.0305(6) Uani d . 1 C C7 0.7984(4) 0.6201(3) 0.3376(2) 0.0328(6) Uani d . 1 C H7 0.8254 0.6665 0.4065 0.039 Uiso calc R 1 H N1 0.7714(4) 0.9974(3) -0.0418(2) 0.0411(6) Uani d D 1 N N2 0.6916(4) 0.7683(3) -0.1463(2) 0.0487(7) Uani d . 1 N C8 0.8217(5) 1.1032(3) 0.0171(3) 0.0525(9) Uani d . 1 C H8 0.8386 1.1050 0.0980 0.063 Uiso calc R 1 H C9 0.8484(5) 1.2098(3) -0.0425(4) 0.0550(9) Uani d . 1 C H9 0.8898 1.2833 -0.0017 0.066 Uiso calc R 1 H C10 0.8145(5) 1.2079(3) -0.1612(3) 0.0511(9) Uani d . 1 C H10 0.8267 1.2813 -0.2017 0.061 Uiso calc R 1 H C11 0.7615(4) 1.0965(3) -0.2228(3) 0.0416(7) Uani d . 1 C C12 0.7238(5) 1.0863(4) -0.3486(3) 0.0524(10) Uani d . 1 C H12 0.7328 1.1573 -0.3930 0.063 Uiso calc R 1 H C13 0.6761(5) 0.9762(4) -0.4023(3) 0.0538(10) Uani d . 1 C H13 0.6511 0.9723 -0.4835 0.065 Uiso calc R 1 H C14 0.6626(4) 0.8643(4) -0.3373(3) 0.0462(8) Uani d . 1 C C15 0.6202(6) 0.7476(5) -0.3887(3) 0.0615(11) Uani d . 1 C H15 0.5965 0.7395 -0.4696 0.074 Uiso calc R 1 H C16 0.6133(6) 0.6455(5) -0.3216(4) 0.0704(12) Uani d . 1 C H16 0.5851 0.5669 -0.3554 0.084 Uiso calc R 1 H C17 0.6494(6) 0.6608(4) -0.1999(4) 0.0636(10) Uani d . 1 C H17 0.6431 0.5903 -0.1545 0.076 Uiso calc R 1 H C18 0.7442(4) 0.9884(3) -0.1589(2) 0.0356(6) Uani d . 1 C C19 0.6969(4) 0.8694(3) -0.2147(3) 0.0400(7) Uani d . 1 C H1 0.997(6) 0.461(4) 0.605(3) 0.080 Uiso d D 1 H H2 0.751(7) 0.935(3) -0.006(4) 0.080 Uiso d D 1 H H3 0.861(6) 0.269(5) 0.303(2) 0.080 Uiso d 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 S1 0.0470(4) 0.0323(3) 0.0220(3) 0.0063(3) 0.0052(2) 0.0012(3) O1 0.0820(17) 0.0438(13) 0.0286(11) 0.0175(12) 0.0006(11) 0.0067(10) O2 0.0834(18) 0.0345(13) 0.0509(14) 0.0020(12) -0.0022(13) 0.0081(10) O3 0.0787(19) 0.0362(13) 0.0490(15) 0.0031(12) 0.0019(13) -0.0064(11) O4 0.0604(13) 0.0406(13) 0.0340(11) 0.0052(10) 0.0013(9) 0.0045(9) O5 0.0604(14) 0.0413(12) 0.0369(12) -0.0035(10) 0.0046(10) -0.0028(10) O6 0.0821(16) 0.0447(15) 0.0433(12) 0.0176(12) 0.0242(11) 0.0021(10) C1 0.0410(17) 0.0347(16) 0.0394(17) 0.0007(13) 0.0068(13) 0.0029(14) C2 0.0322(14) 0.0396(15) 0.0300(14) -0.0018(12) 0.0057(11) -0.0012(13) C3 0.0374(16) 0.0321(16) 0.0465(18) -0.0020(13) 0.0079(14) -0.0046(14) C4 0.0454(17) 0.0483(18) 0.0271(14) -0.0001(14) 0.0012(12) -0.0080(14) C5 0.0406(16) 0.0400(17) 0.0239(14) 0.0009(13) 0.0046(12) -0.0016(12) C6 0.0310(13) 0.0297(14) 0.0304(14) -0.0003(11) 0.0060(11) -0.0025(11) C7 0.0356(15) 0.0341(15) 0.0274(14) -0.0017(12) 0.0047(11) -0.0004(12) N1 0.0552(16) 0.0357(14) 0.0323(13) -0.0031(12) 0.0097(11) -0.0030(12) N2 0.0666(19) 0.0406(15) 0.0392(15) -0.0052(14) 0.0125(13) -0.0049(12) C8 0.058(2) 0.055(2) 0.0453(18) -0.0014(17) 0.0122(16) -0.0108(17) C9 0.062(2) 0.0372(18) 0.068(2) -0.0033(16) 0.0198(18) -0.0079(17) C10 0.0453(18) 0.0377(18) 0.074(3) 0.0027(15) 0.0217(17) 0.0114(17) C11 0.0314(15) 0.0470(19) 0.0482(18) 0.0054(14) 0.0129(13) 0.0106(15) C12 0.0410(18) 0.072(3) 0.0473(19) 0.0103(17) 0.0165(15) 0.0253(19) C13 0.0441(19) 0.086(3) 0.0321(17) 0.0050(18) 0.0108(14) 0.0026(19) C14 0.0324(14) 0.071(2) 0.0356(15) -0.0010(16) 0.0093(11) -0.0043(16) C15 0.059(2) 0.088(3) 0.040(2) -0.020(2) 0.0163(17) -0.026(2) C16 0.076(3) 0.071(3) 0.068(3) -0.024(2) 0.024(2) -0.034(2) C17 0.085(3) 0.050(2) 0.060(2) -0.017(2) 0.025(2) -0.0078(19) C18 0.0308(14) 0.0409(16) 0.0360(15) 0.0010(13) 0.0095(12) -0.0001(14) C19 0.0372(15) 0.049(2) 0.0336(15) -0.0014(13) 0.0072(11) -0.0036(14) 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' S S 0.1246 0.1234 '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 O6 S1 O4 114.28(14) O6 S1 O5 112.90(14) O4 S1 O5 110.69(14) O6 S1 C6 105.93(13) O4 S1 C6 105.79(13) O5 S1 C6 106.57(13) C1 O1 H1 110(3) C3 O3 H3 111(4) O2 C1 O1 124.1(3) O2 C1 C2 121.9(3) O1 C1 C2 114.0(3) C7 C2 C3 119.3(3) C7 C2 C1 120.8(3) C3 C2 C1 119.9(3) O3 C3 C4 118.6(3) O3 C3 C2 122.1(3) C4 C3 C2 119.3(3) C5 C4 C3 120.6(3) C5 C4 H4 119.7 C3 C4 H4 119.7 C4 C5 C6 119.9(3) C4 C5 H5 120.0 C6 C5 H5 120.0 C7 C6 C5 120.7(3) C7 C6 S1 118.8(2) C5 C6 S1 120.5(2) C6 C7 C2 120.2(3) C6 C7 H7 119.9 C2 C7 H7 119.9 C8 N1 C18 123.3(3) C8 N1 H2 119(3) C18 N1 H2 118(3) C17 N2 C19 116.6(3) N1 C8 C9 119.4(3) N1 C8 H8 120.3 C9 C8 H8 120.3 C10 C9 C8 119.9(3) C10 C9 H9 120.0 C8 C9 H9 120.0 C9 C10 C11 120.4(3) C9 C10 H10 119.8 C11 C10 H10 119.8 C10 C11 C18 118.1(3) C10 C11 C12 123.9(3) C18 C11 C12 118.0(3) C13 C12 C11 121.0(3) C13 C12 H12 119.5 C11 C12 H12 119.5 C12 C13 C14 121.4(3) C12 C13 H13 119.3 C14 C13 H13 119.3 C15 C14 C19 116.7(4) C15 C14 C13 123.5(3) C19 C14 C13 119.8(4) C16 C15 C14 120.2(3) C16 C15 H15 119.9 C14 C15 H15 119.9 C15 C16 C17 118.5(4) C15 C16 H16 120.7 C17 C16 H16 120.7 N2 C17 C16 124.1(4) N2 C17 H17 118.0 C16 C17 H17 118.0 N1 C18 C11 118.7(3) N1 C18 C19 119.5(3) C11 C18 C19 121.8(3) N2 C19 C14 123.8(3) N2 C19 C18 118.2(3) C14 C19 C18 118.0(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S1 O6 1.439(2) yes S1 O4 1.454(2) yes S1 O5 1.465(2) yes S1 C6 1.777(3) yes O1 C1 1.306(4) yes O1 H1 0.85(4) ? O2 C1 1.216(4) yes O3 C3 1.344(4) yes O3 H3 0.85(3) ? C1 C2 1.477(4) ? C2 C7 1.398(4) ? C2 C3 1.406(4) ? C3 C4 1.397(5) ? C4 C5 1.376(5) ? C4 H4 0.9300 ? C5 C6 1.384(4) ? C5 H5 0.9300 ? C6 C7 1.379(4) ? C7 H7 0.9300 ? N1 C8 1.328(4) ? N1 C18 1.348(4) ? N1 H2 0.82(4) ? N2 C17 1.309(5) ? N2 C19 1.351(4) ? C8 C9 1.371(5) ? C8 H8 0.9300 ? C9 C10 1.360(5) ? C9 H9 0.9300 ? C10 C11 1.397(5) ? C10 H10 0.9300 ? C11 C18 1.397(5) ? C11 C12 1.443(5) ? C12 C13 1.339(6) ? C12 H12 0.9300 ? C13 C14 1.432(6) ? C13 H13 0.9300 ? C14 C15 1.385(6) ? C14 C19 1.405(4) ? C15 C16 1.353(7) ? C15 H15 0.9300 ? C16 C17 1.402(6) ? C16 H16 0.9300 ? C17 H17 0.9300 ? C18 C19 1.433(5) ? 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 O1 H1 O5 2_746 0.85(4) 1.79(4) 2.623(3) 168(5) yes O3 H3 O2 . 0.85(3) 1.86(3) 2.587(4) 142(5) yes N1 H2 O4 . 0.82(4) 2.10(3) 2.780(4) 141(4) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21129908 2 PubChem 139067464