#------------------------------------------------------------------------------ #$Date: 2025-08-19 15:49:58 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301806 $ #$URL: svn://www.crystallography.net/cod/cif/2/23/89/2238948.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_2238948 loop_ _publ_author_name 'Sahbani, Thameur' 'Smirani Sta, Wajda' 'Rzaigui, Mohamed' _publ_section_title ; Tetraaquabis(piperazin-1-ium)cobalt(II) bis(sulfate) dihydrate ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first m649 _journal_page_last m650 _journal_paper_doi 10.1107/S1600536813030365 _journal_volume 69 _journal_year 2013 _chemical_formula_iupac '[Co (C4 H11 N2)2 (H2 O)4] (S O4)2, 2H2 O' _chemical_formula_moiety 'C8 H30 Co N4 O4 4+, 2(O4 S 2-), 2(H2 O)' _chemical_formula_sum 'C8 H34 Co N4 O14 S2' _chemical_formula_weight 533.46 _chemical_name_systematic ; Tetraaquabis(piperazin-1-ium)cobalt(II) bis(sulfate) dihydrate ; _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _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 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 12.187(2) _cell_length_b 12.980(2) _cell_length_c 13.437(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 11 _cell_measurement_theta_min 9 _cell_volume 2125.6(6) _computing_cell_refinement 'CAD-4 EXPRESS (Enraf--Nonius, 1994)' _computing_data_collection 'CAD-4 EXPRESS (Enraf--Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 2012)' _computing_publication_material 'WinGX (Farrugia, 2012)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 293 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Enraf--Nonius TurboCAD-4' _diffrn_measurement_method 'non-profiled omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type AgK\a _diffrn_radiation_wavelength 0.56085 _diffrn_reflns_av_R_equivalents 0.0228 _diffrn_reflns_av_sigmaI/netI 0.0496 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -2 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -2 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -3 _diffrn_reflns_number 8070 _diffrn_reflns_theta_full 27.96 _diffrn_reflns_theta_max 27.96 _diffrn_reflns_theta_min 2.17 _diffrn_standards_decay_% 5 _diffrn_standards_interval_time 120 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 0.562 _exptl_absorpt_correction_type none _exptl_crystal_colour pink _exptl_crystal_density_diffrn 1.667 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1124 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.725 _refine_diff_density_min -0.345 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 157 _refine_ls_number_reflns 5211 _refine_ls_number_restraints 9 _refine_ls_restrained_S_all 1.037 _refine_ls_R_factor_all 0.0990 _refine_ls_R_factor_gt 0.0450 _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^)+(0.0459P)^2^+0.2397P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0930 _refine_ls_wR_factor_ref 0.1075 _reflns_number_gt 3131 _reflns_number_total 5211 _reflns_threshold_expression I>2sigma(I) _iucr_refine_instructions_details ; TITL cad4 in P b c a CELL 0.56087 12.1866 12.9804 13.4368 90.000 90.000 90.000 ZERR 8.00 0.0020 0.0020 0.0020 0.000 0.000 0.000 LATT 1 SYMM 1/2 - X, - Y, 1/2 + Z SYMM 1/2 + X, 1/2 - Y, - Z SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H CO N O S UNIT 32 136 4 16 56 8 MERG 2 DFIX 0.850 0.020 H1O5 O5 DFIX 0.850 0.020 O5 H2O5 DFIX 1.370 0.020 H1O5 H2O5 DFIX 0.850 0.020 H2O7 O7 DFIX 0.850 0.020 O7 H1O7 DFIX 1.370 0.020 H2O7 H1O7 DFIX 0.850 0.020 H1O6 O6 DFIX 0.850 0.020 O6 H2O6 DFIX 1.370 0.020 H1O6 H2O6 FMAP 2 PLAN 20 SIZE 0.20 0.20 0.20 ACTA BOND $H L.S. 4 TEMP 20.00 WGHT 0.045600 0.246100 FVAR 0.39760 CO1 3 0.500000 0.500000 0.500000 10.50000 0.02119 0.02247 = 0.01973 -0.00212 -0.00085 -0.00208 S 6 0.661582 0.172439 0.583390 11.00000 0.02149 0.02527 = 0.02214 -0.00082 -0.00176 0.00342 N1 4 0.484878 0.556790 0.346322 11.00000 0.02586 0.02702 = 0.02118 -0.00026 0.00073 -0.00133 AFIX 13 H5 2 0.436676 0.610214 0.349772 11.00000 -1.20000 AFIX 0 O5 5 0.665031 0.466568 0.487318 11.00000 0.02426 0.03916 = 0.03969 -0.01339 -0.00041 0.00092 N2 4 0.516885 0.578864 0.133838 11.00000 0.03084 0.03407 = 0.02198 0.00453 0.00070 0.00267 AFIX 23 H9A 2 0.501459 0.611495 0.076419 11.00000 -1.20000 H9B 2 0.565405 0.528466 0.120435 11.00000 -1.20000 AFIX 0 O1 5 0.554778 0.181236 0.532805 11.00000 0.03272 0.04408 = 0.04737 -0.01226 -0.02026 0.01111 O4 5 0.680945 0.063055 0.607677 11.00000 0.03142 0.02821 = 0.04925 0.00868 0.00581 0.00518 O3 5 0.659641 0.234675 0.672764 11.00000 0.06092 0.05038 = 0.03506 -0.01853 -0.01318 0.01375 C4 1 0.436261 0.484095 0.274345 11.00000 0.03295 0.03776 = 0.02276 0.00214 -0.00269 -0.01263 AFIX 23 H4A 2 0.367658 0.458125 0.301004 11.00000 -1.20000 H4B 2 0.485441 0.426001 0.265842 11.00000 -1.20000 AFIX 0 O2 5 0.749587 0.206474 0.517213 11.00000 0.03752 0.05295 = 0.06180 0.02792 0.01921 0.01029 C1 1 0.585588 0.600926 0.303413 11.00000 0.03260 0.04175 = 0.02513 0.00280 -0.00250 -0.01344 AFIX 23 H1A 2 0.639179 0.546402 0.294772 11.00000 -1.20000 H1B 2 0.615934 0.650539 0.349854 11.00000 -1.20000 AFIX 0 C2 1 0.567057 0.653203 0.204745 11.00000 0.04219 0.03179 = 0.02970 0.00676 0.00206 -0.00854 AFIX 23 H2A 2 0.518820 0.711952 0.213486 11.00000 -1.20000 H2B 2 0.636389 0.677825 0.178448 11.00000 -1.20000 AFIX 0 C3 1 0.414965 0.532647 0.174274 11.00000 0.03173 0.05354 = 0.02708 0.00491 -0.00710 -0.00730 AFIX 23 H3A 2 0.387806 0.480794 0.128498 11.00000 -1.20000 H3B 2 0.359210 0.585532 0.180926 11.00000 -1.20000 AFIX 0 O6 5 0.460370 0.350309 0.455715 11.00000 0.03141 0.02531 = 0.03416 -0.00208 -0.00612 -0.00103 O7 5 0.745635 0.333818 0.354040 11.00000 0.06444 0.04048 = 0.03243 -0.00160 0.00143 0.00143 H1O5 2 0.716579 0.494386 0.517549 11.00000 0.04621 H2O5 2 0.690044 0.425263 0.444223 11.00000 0.04457 H1O7 2 0.713888 0.320391 0.301469 11.00000 0.06529 H2O7 2 0.744908 0.286472 0.394328 11.00000 0.06120 H1O6 2 0.393106 0.335368 0.462932 11.00000 0.04908 H2O6 2 0.497474 0.303169 0.483042 11.00000 0.06303 HKLF 4 REM cad4 in P b c a REM R1 = 0.0450 for 3131 Fo > 4sig(Fo) and 0.0990 for all 5211 data REM 157 parameters refined using 9 restraints END WGHT 0.0456 0.2461 REM Highest difference peak 0.725, deepest hole -0.345, 1-sigma level 0.084 Q1 1 0.5016 0.4434 0.5170 11.00000 0.05 0.73 Q2 1 0.6640 0.1126 0.5891 11.00000 0.05 0.68 Q3 1 0.7406 0.1565 0.5039 11.00000 0.05 0.45 Q4 1 0.6567 0.0856 0.6476 11.00000 0.05 0.45 Q5 1 0.5834 0.1980 0.5667 11.00000 0.05 0.43 Q6 1 0.5966 0.2031 0.5029 11.00000 0.05 0.35 Q7 1 0.6593 0.2254 0.6231 11.00000 0.05 0.34 Q8 1 0.4971 0.3082 0.4500 11.00000 0.05 0.32 Q9 1 0.4851 0.3912 0.4865 11.00000 0.05 0.31 Q10 1 0.4147 0.4262 0.2890 11.00000 0.05 0.31 Q11 1 0.7742 0.2229 0.5056 11.00000 0.05 0.31 Q12 1 0.5798 0.7473 0.2022 11.00000 0.05 0.31 Q13 1 0.5743 0.6254 0.2550 11.00000 0.05 0.30 Q14 1 0.6042 0.2053 0.6761 11.00000 0.05 0.30 Q15 1 0.5225 0.6265 0.1680 11.00000 0.05 0.30 Q16 1 0.5400 0.5740 0.3262 11.00000 0.05 0.30 Q17 1 0.5216 0.1787 0.5280 11.00000 0.05 0.29 Q18 1 0.6788 0.0557 0.5618 11.00000 0.05 0.29 Q19 1 0.7138 0.0592 0.6126 11.00000 0.05 0.29 Q20 1 0.5155 0.4020 0.4293 11.00000 0.05 0.28 ; _cod_data_source_file zl2569.cif _cod_data_source_block I _cod_original_cell_volume 2125.5(6) _cod_database_code 2238948 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 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 _atom_site_symmetry_multiplicity Co Co1 0.5000 0.5000 0.5000 0.02113(7) Uani d S 1 2 S S 0.66158(3) 0.17244(3) 0.58339(3) 0.02297(8) Uani d . 1 1 N N1 0.48488(11) 0.55679(11) 0.34632(10) 0.0247(3) Uani d . 1 1 H H5 0.4367 0.6102 0.3498 0.030 Uiso calc R 1 1 O O5 0.66503(11) 0.46657(12) 0.48732(11) 0.0344(3) Uani d D 1 1 N N2 0.51689(12) 0.57886(12) 0.13384(11) 0.0290(3) Uani d . 1 1 H H9A 0.5015 0.6115 0.0764 0.035 Uiso calc R 1 1 H H9B 0.5654 0.5285 0.1204 0.035 Uiso calc R 1 1 O O1 0.55478(12) 0.18124(11) 0.53281(12) 0.0414(4) Uani d . 1 1 O O4 0.68095(11) 0.06305(10) 0.60768(11) 0.0363(3) Uani d . 1 1 O O3 0.65964(14) 0.23468(12) 0.67276(11) 0.0488(4) Uani d . 1 1 C C4 0.43626(16) 0.48409(15) 0.27435(13) 0.0312(4) Uani d . 1 1 H H4A 0.3677 0.4581 0.3010 0.037 Uiso calc R 1 1 H H4B 0.4854 0.4260 0.2658 0.037 Uiso calc R 1 1 O O2 0.74959(13) 0.20647(14) 0.51721(13) 0.0508(4) Uani d . 1 1 C C1 0.58559(16) 0.60093(16) 0.30341(13) 0.0332(4) Uani d . 1 1 H H1A 0.6392 0.5464 0.2948 0.040 Uiso calc R 1 1 H H1B 0.6159 0.6505 0.3499 0.040 Uiso calc R 1 1 C C2 0.56706(18) 0.65320(15) 0.20475(14) 0.0346(4) Uani d . 1 1 H H2A 0.5188 0.7120 0.2135 0.041 Uiso calc R 1 1 H H2B 0.6364 0.6778 0.1784 0.041 Uiso calc R 1 1 C C3 0.41497(16) 0.53265(19) 0.17427(14) 0.0375(4) Uani d . 1 1 H H3A 0.3878 0.4808 0.1285 0.045 Uiso calc R 1 1 H H3B 0.3592 0.5855 0.1809 0.045 Uiso calc R 1 1 O O6 0.46037(12) 0.35031(10) 0.45571(11) 0.0303(3) Uani d D 1 1 O O7 0.74564(16) 0.33382(12) 0.35404(12) 0.0458(4) Uani d D 1 1 H H1O5 0.7166(17) 0.4944(17) 0.5175(17) 0.046(8) Uiso d D 1 1 H H2O5 0.6900(18) 0.4253(16) 0.4442(14) 0.045(7) Uiso d D 1 1 H H1O7 0.714(2) 0.320(2) 0.3015(14) 0.065(9) Uiso d D 1 1 H H2O7 0.745(2) 0.2865(17) 0.3943(15) 0.061(9) Uiso d D 1 1 H H1O6 0.3931(12) 0.3354(18) 0.4629(19) 0.049(7) Uiso d D 1 1 H H2O6 0.4975(17) 0.3032(18) 0.4830(19) 0.063(10) Uiso d D 1 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 Co1 0.02119(12) 0.02247(13) 0.01973(12) -0.00208(12) -0.00085(12) -0.00212(12) S 0.02149(16) 0.02527(17) 0.02214(16) 0.00342(15) -0.00176(15) -0.00082(16) N1 0.0259(7) 0.0270(6) 0.0212(6) -0.0013(5) 0.0007(5) -0.0003(5) O5 0.0243(6) 0.0392(7) 0.0397(7) 0.0009(6) -0.0004(6) -0.0134(6) N2 0.0308(8) 0.0341(7) 0.0220(6) 0.0027(6) 0.0007(6) 0.0045(6) O1 0.0327(7) 0.0441(8) 0.0474(8) 0.0111(7) -0.0203(6) -0.0123(7) O4 0.0314(7) 0.0282(6) 0.0492(8) 0.0052(5) 0.0058(6) 0.0087(6) O3 0.0609(10) 0.0504(9) 0.0351(7) 0.0137(8) -0.0132(7) -0.0185(7) C4 0.0329(8) 0.0378(10) 0.0228(7) -0.0126(8) -0.0027(7) 0.0021(7) O2 0.0375(8) 0.0530(9) 0.0618(10) 0.0103(7) 0.0192(8) 0.0279(8) C1 0.0326(9) 0.0417(10) 0.0251(8) -0.0134(8) -0.0025(7) 0.0028(8) C2 0.0422(10) 0.0318(9) 0.0297(8) -0.0085(8) 0.0021(8) 0.0068(8) C3 0.0317(9) 0.0535(11) 0.0271(8) -0.0073(9) -0.0071(8) 0.0049(9) O6 0.0314(6) 0.0253(6) 0.0342(7) -0.0010(5) -0.0061(6) -0.0021(5) O7 0.0644(10) 0.0405(8) 0.0324(7) 0.0014(8) 0.0014(8) -0.0016(7) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0015 0.0009 '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' Co Co 0.3050 0.6296 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.0826 0.0763 '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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle O5 Co1 O5 . 5_666 180.0 O5 Co1 O6 . . 90.35(6) O5 Co1 O6 5_666 . 89.65(6) O5 Co1 O6 . 5_666 89.65(6) O5 Co1 O6 5_666 5_666 90.35(6) O6 Co1 O6 . 5_666 180.0 O5 Co1 N1 . 5_666 85.72(6) O5 Co1 N1 5_666 5_666 94.28(6) O6 Co1 N1 . 5_666 88.57(5) O6 Co1 N1 5_666 5_666 91.43(5) O5 Co1 N1 . . 94.28(6) O5 Co1 N1 5_666 . 85.72(6) O6 Co1 N1 . . 91.43(5) O6 Co1 N1 5_666 . 88.57(5) N1 Co1 N1 5_666 . 180.0 O3 S O2 . . 110.37(11) O3 S O1 . . 108.98(9) O2 S O1 . . 110.14(10) O3 S O4 . . 110.86(9) O2 S O4 . . 107.94(9) O1 S O4 . . 108.54(8) C1 N1 C4 . . 109.08(14) C1 N1 Co1 . . 115.35(11) C4 N1 Co1 . . 115.76(10) C1 N1 H5 . . 105.2 C4 N1 H5 . . 105.2 Co1 N1 H5 . . 105.2 Co1 O5 H1O5 . . 127.2(16) Co1 O5 H2O5 . . 122.7(16) H1O5 O5 H2O5 . . 109.7(19) C3 N2 C2 . . 111.85(15) C3 N2 H9A . . 109.2 C2 N2 H9A . . 109.2 C3 N2 H9B . . 109.2 C2 N2 H9B . . 109.2 H9A N2 H9B . . 107.9 N1 C4 C3 . . 112.73(15) N1 C4 H4A . . 109.0 C3 C4 H4A . . 109.0 N1 C4 H4B . . 109.0 C3 C4 H4B . . 109.0 H4A C4 H4B . . 107.8 N1 C1 C2 . . 113.27(16) N1 C1 H1A . . 108.9 C2 C1 H1A . . 108.9 N1 C1 H1B . . 108.9 C2 C1 H1B . . 108.9 H1A C1 H1B . . 107.7 N2 C2 C1 . . 109.46(15) N2 C2 H2A . . 109.8 C1 C2 H2A . . 109.8 N2 C2 H2B . . 109.8 C1 C2 H2B . . 109.8 H2A C2 H2B . . 108.2 N2 C3 C4 . . 110.60(15) N2 C3 H3A . . 109.5 C4 C3 H3A . . 109.5 N2 C3 H3B . . 109.5 C4 C3 H3B . . 109.5 H3A C3 H3B . . 108.1 Co1 O6 H1O6 . . 113.8(17) Co1 O6 H2O6 . . 115.2(19) H1O6 O6 H2O6 . . 107.6(19) H1O7 O7 H2O7 . . 114(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance Co1 O5 . 2.0645(14) Co1 O5 5_666 2.0645(14) Co1 O6 . 2.0887(13) Co1 O6 5_666 2.0887(13) Co1 N1 5_666 2.2003(14) Co1 N1 . 2.2003(14) S O3 . 1.4475(15) S O2 . 1.4615(15) S O1 . 1.4728(14) S O4 . 1.4759(13) N1 C1 . 1.472(2) N1 C4 . 1.475(2) N1 H5 . 0.9100 O5 H1O5 . 0.831(15) O5 H2O5 . 0.846(15) N2 C3 . 1.483(2) N2 C2 . 1.488(2) N2 H9A . 0.9000 N2 H9B . 0.9000 C4 C3 . 1.508(2) C4 H4A . 0.9700 C4 H4B . 0.9700 C1 C2 . 1.506(3) C1 H1A . 0.9700 C1 H1B . 0.9700 C2 H2A . 0.9700 C2 H2B . 0.9700 C3 H3A . 0.9700 C3 H3B . 0.9700 O6 H1O6 . 0.848(15) O6 H2O6 . 0.845(16) O7 H1O7 . 0.824(16) O7 H2O7 . 0.819(15) 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 H1O5 O4 7_765 0.83(2) 1.96(2) 2.776(2) 170(2) yes O5 H2O5 O7 1_555 0.85(2) 1.83(2) 2.672(2) 178(2) yes O7 H1O7 O3 8_565 0.82(2) 1.98(2) 2.797(2) 169(2) yes O7 H2O7 O2 1_555 0.82(2) 1.95(2) 2.746(2) 163(2) yes N1 H5 O3 5_666 0.91 2.35 3.240(2) 166 yes O6 H1O6 O2 3_456 0.848(15) 1.851(16) 2.697(2) 176(3) yes O6 H2O6 O1 1_555 0.84(2) 1.86(2) 2.686(2) 168(2) yes N2 H9A O1 4_655 0.90 1.86 2.747(2) 170 yes N2 H9B O4 8_565 0.90 1.85 2.741(2) 170 yes C3 H3A O7 6_556 0.97 2.59 3.326(3) 133 yes C4 H4A O4 3_456 0.97 2.60 3.545(2) 165 yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 168326305