#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/36/2203636.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_2203636 loop_ _publ_author_name 'Mazur, Liliana' 'Tokarska, Joanna' 'Koziol, Anna E.' 'Kopacz, Maria' _publ_section_title ; Ammonium quercetin-5'-sulfonate formamide solvate ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o779 _journal_page_last o781 _journal_paper_doi 10.1107/S1600536804008153 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'H4 N1 + , C15 H9 O10 S - , C H3 N O' _chemical_formula_moiety 'H4 N1 + , C15 H9 O10 S - , C H3 N O' _chemical_formula_sum 'C16 H16 N2 O11 S' _chemical_formula_weight 444.37 _chemical_name_common 'ammonium quercetin-5'-sulfonate formamide solvate' _chemical_name_systematic ; ammonium 2,3-dihydroxy-5-(3,5,7-trihydroxy-4-oxo-4H-1-benzopyran-2-yl)benzenesulfonate formamide solvate ; _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 _cell_angle_alpha 68.25(3) _cell_angle_beta 86.54(2) _cell_angle_gamma 84.40(2) _cell_formula_units_Z 2 _cell_length_a 7.878(2) _cell_length_b 10.584(4) _cell_length_c 11.184(4) _cell_measurement_reflns_used 40 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 19 _cell_measurement_theta_min 6 _cell_volume 861.7(5) _computing_cell_refinement 'KM-4 Software' _computing_data_collection 'KM-4 Software (Kuma Diffraction, 1991)' _computing_data_reduction 'KM-4 Software' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1990)' _computing_publication_material 'SHELXL97 and enCIFer (Allen et al., 2004)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.977 _diffrn_measured_fraction_theta_max 0.977 _diffrn_measurement_device_type 'Kuma KM4 four-circle' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0381 _diffrn_reflns_av_sigmaI/netI 0.0945 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3838 _diffrn_reflns_theta_full 80.25 _diffrn_reflns_theta_max 80.25 _diffrn_reflns_theta_min 5.64 _diffrn_standards_decay_% 1.33 _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 2.346 _exptl_absorpt_correction_T_max 0.81 _exptl_absorpt_correction_T_min 0.78 _exptl_absorpt_correction_type cylinder _exptl_absorpt_process_details '(KM-4; Kuma Diffraction, 1991)' _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.713 _exptl_crystal_density_meas ? _exptl_crystal_density_method . _exptl_crystal_description needle _exptl_crystal_F_000 460 _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.09 _refine_diff_density_max 0.422 _refine_diff_density_min -0.423 _refine_ls_extinction_coef 0.0048(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 290 _refine_ls_number_reflns 3666 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.001 _refine_ls_R_factor_all 0.1314 _refine_ls_R_factor_gt 0.0489 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0846P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1156 _refine_ls_wR_factor_ref 0.1425 _reflns_number_gt 1957 _reflns_number_total 3666 _reflns_threshold_expression I>2\s(I) _cod_data_source_file na6313.cif _cod_data_source_block I _cod_database_code 2203636 _cod_database_fobs_code 2203636 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -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 N1 0.2128(5) 1.0432(4) 0.5837(3) 0.0458(7) Uani d . 1 N H1N 0.249(6) 1.119(5) 0.591(4) 0.064 Uiso d . 1 H H2N 0.106(6) 1.038(5) 0.589(5) 0.064 Uiso d . 1 H H3N 0.235(6) 0.972(5) 0.646(5) 0.064 Uiso d . 1 H H4N 0.263(6) 1.036(5) 0.509(5) 0.064 Uiso d . 1 H O1 0.5810(3) 0.5951(2) 0.1374(2) 0.0324(5) Uani d . 1 O C2 0.5031(4) 0.5020(3) 0.2415(3) 0.0293(6) Uani d . 1 C C3 0.5295(4) 0.3664(3) 0.2635(3) 0.0330(7) Uani d . 1 C O3 0.4526(3) 0.2708(2) 0.3628(2) 0.0433(6) Uani d . 1 O H3 0.4892 0.1882 0.3623 0.052 Uiso d R 1 H C4 0.6411(4) 0.3179(3) 0.1805(3) 0.0321(7) Uani d . 1 C O4 0.6666(3) 0.1916(2) 0.2042(2) 0.0424(6) Uani d . 1 O C5 0.8187(4) 0.3837(3) -0.0230(3) 0.0317(6) Uani d . 1 C O5 0.8524(3) 0.2522(2) -0.0092(2) 0.0447(6) Uani d . 1 O H5 0.7864 0.2021 0.0616 0.054 Uiso d R 1 H C6 0.8863(4) 0.4841(3) -0.1268(3) 0.0353(7) Uani d . 1 C H6 0.9539 0.4612 -0.1880 0.042 Uiso calc R 1 H C7 0.8535(4) 0.6201(3) -0.1403(3) 0.0316(6) Uani d . 1 C O7 0.9293(3) 0.7127(2) -0.2430(2) 0.0402(6) Uani d . 1 O H7 0.9065 0.8011 -0.2531 0.048 Uiso d R 1 H C8 0.7488(4) 0.6601(3) -0.0524(3) 0.0304(6) Uani d . 1 C H8 0.7258 0.7514 -0.0632 0.036 Uiso calc R 1 H C9 0.6814(4) 0.5567(3) 0.0515(3) 0.0284(6) Uani d . 1 C C10 0.7140(4) 0.4187(3) 0.0703(3) 0.0296(6) Uani d . 1 C C1' 0.3984(4) 0.5708(3) 0.3171(3) 0.0274(6) Uani d . 1 C C2' 0.3135(4) 0.4970(3) 0.4331(3) 0.0319(6) Uani d . 1 C H2' 0.3197 0.4022 0.4628 0.038 Uiso calc R 1 H C3' 0.2213(4) 0.5655(3) 0.5024(3) 0.0316(6) Uani d . 1 C O3' 0.1364(3) 0.5024(2) 0.6152(2) 0.0415(6) Uani d . 1 O H3' 0.1582 0.4126 0.6362 0.050 Uiso d R 1 H C4' 0.2112(4) 0.7079(3) 0.4599(3) 0.0300(6) Uani d . 1 C O4' 0.1232(3) 0.7743(2) 0.5310(2) 0.0400(6) Uani d . 1 O H4' 0.0654 0.7194 0.6030 0.048 Uiso d R 1 H C5' 0.2930(4) 0.7807(3) 0.3451(3) 0.0306(6) Uani d . 1 C S1 0.29527(11) 0.95979(7) 0.29027(8) 0.0337(2) Uani d . 1 S O1S 0.3692(3) 1.0018(2) 0.1610(2) 0.0431(6) Uani d . 1 O O2S 0.3986(3) 0.9898(2) 0.3791(2) 0.0447(6) Uani d . 1 O O3S 0.1193(3) 1.0168(2) 0.2918(3) 0.0499(7) Uani d . 1 O C6' 0.3862(4) 0.7124(3) 0.2741(3) 0.0302(6) Uani d . 1 C H6' 0.4406 0.7621 0.1972 0.036 Uiso calc R 1 H O1F 0.1998(4) 1.2317(2) -0.2929(2) 0.0500(7) Uani d . 1 O C1F 0.1793(5) 1.1738(4) -0.1751(4) 0.0505(9) Uani d . 1 C H1F 0.0833 1.1973 -0.1277 0.061 Uiso d R 1 H N1F 0.2693(5) 1.0639(4) -0.1041(3) 0.0529(8) Uani d . 1 N H2F 0.237(7) 1.036(5) -0.030(5) 0.074 Uiso d . 1 H H3F 0.360(6) 1.025(5) -0.145(5) 0.074 Uiso 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 N1 0.0495(19) 0.0471(17) 0.0447(18) -0.0080(14) 0.0106(15) -0.0222(14) O1 0.0404(12) 0.0263(9) 0.0295(11) -0.0041(8) 0.0126(9) -0.0107(8) C2 0.0323(15) 0.0290(14) 0.0252(14) -0.0032(11) 0.0079(11) -0.0096(11) C3 0.0387(16) 0.0273(14) 0.0320(16) -0.0047(12) 0.0109(13) -0.0108(12) O3 0.0519(14) 0.0266(10) 0.0444(14) -0.0058(9) 0.0221(11) -0.0078(10) C4 0.0336(16) 0.0280(13) 0.0342(16) -0.0046(11) 0.0086(13) -0.0116(12) O4 0.0506(14) 0.0257(10) 0.0494(14) -0.0031(9) 0.0182(11) -0.0149(10) C5 0.0315(14) 0.0280(13) 0.0368(16) 0.0008(11) 0.0055(12) -0.0150(12) O5 0.0574(15) 0.0285(10) 0.0476(14) -0.0049(10) 0.0229(12) -0.0167(10) C6 0.0356(16) 0.0370(16) 0.0340(16) 0.0018(12) 0.0067(13) -0.0162(13) C7 0.0321(15) 0.0308(14) 0.0287(15) -0.0030(11) 0.0069(12) -0.0081(12) O7 0.0502(14) 0.0298(10) 0.0339(12) -0.0024(9) 0.0194(10) -0.0070(9) C8 0.0326(15) 0.0245(12) 0.0331(15) -0.0013(10) 0.0067(12) -0.0107(11) C9 0.0326(15) 0.0286(13) 0.0244(14) -0.0029(11) 0.0037(11) -0.0108(11) C10 0.0275(14) 0.0313(14) 0.0313(15) -0.0038(11) 0.0049(12) -0.0135(12) C1' 0.0262(13) 0.0270(13) 0.0298(14) -0.0014(10) 0.0052(11) -0.0123(11) C2' 0.0374(15) 0.0254(13) 0.0311(15) -0.0044(11) 0.0060(12) -0.0090(12) C3' 0.0373(16) 0.0301(14) 0.0260(15) -0.0060(12) 0.0092(12) -0.0094(12) O3' 0.0562(15) 0.0285(10) 0.0349(12) -0.0046(10) 0.0216(11) -0.0091(9) C4' 0.0338(15) 0.0280(13) 0.0279(15) -0.0002(11) 0.0070(12) -0.0118(12) O4' 0.0529(14) 0.0299(11) 0.0324(12) -0.0004(9) 0.0197(10) -0.0098(9) C5' 0.0345(15) 0.0266(13) 0.0291(15) -0.0015(11) 0.0069(12) -0.0097(11) S1 0.0411(4) 0.0236(3) 0.0331(4) -0.0014(3) 0.0125(3) -0.0091(3) O1S 0.0613(16) 0.0287(10) 0.0329(12) -0.0050(10) 0.0150(11) -0.0060(9) O2S 0.0559(15) 0.0372(12) 0.0448(14) -0.0119(10) 0.0073(11) -0.0189(10) O3S 0.0431(14) 0.0284(11) 0.0688(18) 0.0029(9) 0.0150(12) -0.0108(11) C6' 0.0334(15) 0.0288(14) 0.0286(15) -0.0002(11) 0.0058(12) -0.0125(11) O1F 0.0739(18) 0.0351(12) 0.0372(13) -0.0014(12) 0.0041(12) -0.0102(10) C1F 0.059(2) 0.046(2) 0.047(2) 0.0003(17) 0.0119(18) -0.0205(17) N1F 0.064(2) 0.0469(17) 0.0407(17) 0.0027(15) 0.0064(16) -0.0107(14) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 '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 _geom_angle_publ_flag H1n N1 H2n 116(5) no H1n N1 H3n 114(5) no H2n N1 H3n 96(4) no H1n N1 H4n 107(4) no H2n N1 H4n 114(4) no H3n N1 H4n 110(4) no C9 O1 C2 122.0(2) yes C3 C2 O1 120.0(2) no C3 C2 C1' 129.0(3) yes O1 C2 C1' 111.0(2) yes O3 C3 C2 122.4(3) no O3 C3 C4 116.6(3) yes C2 C3 C4 121.0(3) no C3 O3 H3 108.8 no O4 C4 C10 123.0(3) no O4 C4 C3 119.9(3) no C10 C4 C3 117.1(3) no O5 C5 C6 119.8(3) no O5 C5 C10 120.1(3) no C6 C5 C10 120.2(3) no C5 O5 H5 106.1 no C5 C6 C7 119.9(3) no C5 C6 H6 120.1 no C7 C6 H6 120.1 no O7 C7 C6 116.3(3) no O7 C7 C8 121.5(3) no C6 C7 C8 122.2(3) no C7 O7 H7 116.6 no C9 C8 C7 116.8(3) no C9 C8 H8 121.6 no C7 C8 H8 121.6 no O1 C9 C8 116.9(2) no O1 C9 C10 120.2(2) no C8 C9 C10 122.8(3) no C9 C10 C5 118.1(3) no C9 C10 C4 119.6(3) no C5 C10 C4 122.3(3) no C6' C1' C2' 119.0(3) no C6' C1' C2 119.0(3) no C2' C1' C2 122.0(2) no C3' C2' C1' 119.9(3) no C3' C2' H2' 120.0 no C1' C2' H2' 120.0 no O3' C3' C2' 123.7(3) no O3' C3' C4' 115.3(3) no C2' C3' C4' 121.0(3) no C3' O3' H3' 107.7 no O4' C4' C5' 120.4(2) no O4' C4' C3' 120.4(2) no C5' C4' C3' 119.1(3) no C4' O4' H4' 115.3 no C4' C5' C6' 120.3(3) no C4' C5' S1 121.5(2) no C6' C5' S1 118.1(2) no O1s S1 O3s 111.92(16) no O1s S1 O2s 112.48(15) no O3s S1 O2s 111.29(16) no O1s S1 C5' 106.08(14) no O3s S1 C5' 107.62(15) no O2s S1 C5' 107.07(15) no C1' C6' C5' 120.7(3) no C1' C6' H6' 119.7 no C5' C6' H6' 119.7 no O1f C1f N1f 124.7(4) no O1f C1f H1f 122.8 no N1f C1f H1f 112.0 no C1f N1f H2f 113(4) no C1f N1f H3f 119(3) no H2f N1f H3f 128(5) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 H1n 0.91(5) no N1 H2n 0.84(5) no N1 H3n 0.83(5) no N1 H4n 0.92(5) no O1 C9 1.359(3) yes O1 C2 1.373(3) yes C2 C3 1.361(4) yes C2 C1' 1.475(4) yes C3 O3 1.352(3) yes C3 C4 1.437(4) yes O3 H3 0.8950 no C4 O4 1.260(3) yes C4 C10 1.430(4) no C5 O5 1.344(3) yes C5 C6 1.371(4) no C5 C10 1.424(4) no O5 H5 0.9335 no C6 C7 1.390(4) no C6 H6 0.9300 no C7 O7 1.354(3) yes C7 C8 1.403(4) no O7 H7 0.9014 no C8 C9 1.388(4) no C8 H8 0.9300 no C9 C10 1.397(4) no C1' C6' 1.389(4) no C1' C2' 1.410(4) no C2' C3' 1.379(4) no C2' H2' 0.9300 no C3' O3' 1.358(3) yes C3' C4' 1.398(4) no O3' H3' 0.8919 no C4' O4' 1.364(3) yes C4' C5' 1.387(4) no O4' H4' 0.9240 no C5' C6' 1.394(4) no C5' S1 1.764(3) yes S1 O1s 1.449(2) yes S1 O2s 1.460(3) yes S1 O3s 1.459(3) yes C6' H6' 0.9300 no O1f C1f 1.238(4) no C1f N1f 1.307(5) no C1f H1f 0.9626 no N1f H2f 0.80(5) no N1f H3f 0.96(5) 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 O5 H5 O4 . 0.93 1.78 2.623(3) 149 yes O3 H3 O4 . 0.90 2.18 2.675(3) 114 yes C2' H2' O3 . 0.93 2.24 2.886(4) 126 yes C6' H6' O1 . 0.93 2.28 2.643(3) 103 yes O7 H7 O3s 2_675 0.90 1.81 2.701(3) 172 yes C8 H8 O1s 2_675 0.93 2.49 3.378(4) 161 yes O4' H4' O7 1_456 0.92 1.96 2.766(3) 146 yes C6 H6 O3' 1_654 0.93 2.48 3.350(4) 157 yes O3 H3 O2s 1_545 0.90 2.22 2.982(3) 143 yes N1 H4n O2s . 0.92(5) 1.94(5) 2.845(4) 168(5) yes N1 H2n O3s 2_576 0.84(5) 2.15(5) 2.901(4) 149(5) yes N1 H2n O4' 2_576 0.84(5) 2.58(5) 3.155(5) 127(5) yes N1 H3n O4 2_666 0.83(5) 2.04(5) 2.855(5) 170(5) yes N1f H2f O1s . 0.80(5) 2.32(5) 2.929(4) 133(5) yes N1f H3f O1s 2_675 0.96(5) 2.14(5) 2.954(5) 142(5) yes O3' H3' O1f 1_546 0.89 1.79 2.668(3) 170 yes C1f H1f O5 1_465 0.96 2.34 3.303(5) 179 yes N1 H1n O1f 1_556 0.91(5) 2.06(5) 2.808(4) 138(5) yes 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 C9 O1 C2 C3 2.0(4) yes C9 O1 C2 C1' -178.5(3) no O1 C2 C3 O3 -178.3(3) no C1' C2 C3 O3 2.4(6) no O1 C2 C3 C4 1.2(5) yes C1' C2 C3 C4 -178.1(3) no O3 C3 C4 O4 -1.9(5) no C2 C3 C4 O4 178.5(3) no O3 C3 C4 C10 175.9(3) no C2 C3 C4 C10 -3.7(5) no O5 C5 C6 C7 -179.2(3) no C10 C5 C6 C7 0.5(5) no C5 C6 C7 O7 177.9(3) no C5 C6 C7 C8 -1.6(5) no O7 C7 C8 C9 -178.2(3) no C6 C7 C8 C9 1.3(5) no C2 O1 C9 C8 177.9(3) yes C2 O1 C9 C10 -2.7(4) no C7 C8 C9 O1 179.5(3) yes C7 C8 C9 C10 0.1(5) no O1 C9 C10 C5 179.5(3) no C8 C9 C10 C5 -1.1(5) no O1 C9 C10 C4 0.0(4) no C8 C9 C10 C4 179.4(3) no O5 C5 C10 C9 -179.5(3) no C6 C5 C10 C9 0.8(5) no O5 C5 C10 C4 0.0(5) no C6 C5 C10 C4 -179.7(3) no O4 C4 C10 C9 -179.2(3) no C3 C4 C10 C9 3.0(5) no O4 C4 C10 C5 1.3(5) no C3 C4 C10 C5 -176.4(3) no C3 C2 C1' C6' -178.2(3) no O1 C2 C1' C6' 2.4(4) yes C3 C2 C1' C2' 3.2(5) no O1 C2 C1' C2' -176.1(3) no C6' C1' C2' C3' -0.5(5) no C2 C1' C2' C3' 178.0(3) no C1' C2' C3' O3' -179.7(3) no C1' C2' C3' C4' -0.5(5) no O3' C3' C4' O4' 1.0(5) no C2' C3' C4' O4' -178.3(3) no O3' C3' C4' C5' -179.5(3) no C2' C3' C4' C5' 1.2(5) no O4' C4' C5' C6' 178.5(3) no C3' C4' C5' C6' -1.0(5) no O4' C4' C5' S1 3.0(4) yes C3' C4' C5' S1 -176.5(2) no C4' C5' S1 O1s -172.0(3) yes C6' C5' S1 O1s 12.4(3) no C4' C5' S1 O3s -52.1(3) no C6' C5' S1 O3s 132.3(3) no C4' C5' S1 O2s 67.7(3) no C6' C5' S1 O2s -107.9(3) no C2' C1' C6' C5' 0.7(5) no C2 C1' C6' C5' -177.9(3) no C4' C5' C6' C1' 0.1(5) no S1 C5' C6' C1' 175.7(2) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21130856 2 PubChem 139066672