#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/61/2006106.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_2006106 loop_ _publ_author_name 'Jones, Peter G.' 'Ernst, Ludger' 'Dix, Ina' 'Wittkowski, Lars' _publ_section_title ; A Diastereomeric Pair of Cyclophane Derivatives: Planar--Chiral and meso-Dimethylbis([2.2]paracyclophan-4-yl)silane ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 612 _journal_page_last 615 _journal_paper_doi 10.1107/S0108270197000085 _journal_volume 53 _journal_year 1997 _chemical_formula_sum 'C34 H36 Si' _chemical_formula_weight 472.72 _chemical_name_systematic ; chiral dimethyl-bis([2.2]paracyclophan-4-yl)silane ; _chemical_temperature_decomposition 180 _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' _audit_creation_method SHELXL _cell_angle_alpha 90 _cell_angle_beta 93.089(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.941(2) _cell_length_b 17.694(2) _cell_length_c 10.4379(14) _cell_measurement_reflns_used 63 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 12.5 _cell_measurement_theta_min 4.7 _cell_volume 2571.0(6) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1991)' _computing_data_reduction XSCANS _computing_molecular_graphics 'XP (Siemens, 1994)' _computing_publication_material SHELXL93 _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 173(2) _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method \w _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 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0641 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 4837 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_min 3.02 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 247 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.221 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 1016 _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.26 _refine_diff_density_max 0.676 _refine_diff_density_min -0.206 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 0.920 _refine_ls_goodness_of_fit_obs 1.059 _refine_ls_hydrogen_treatment 'H atoms: methyl H atoms rigid, others riding' _refine_ls_matrix_type full _refine_ls_number_parameters 318 _refine_ls_number_reflns 4527 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.933 _refine_ls_restrained_S_obs 1.059 _refine_ls_R_factor_all 0.0780 _refine_ls_R_factor_obs .0457 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0599P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1144 _refine_ls_wR_factor_obs .1034 _reflns_number_observed 2972 _reflns_number_total 4530 _reflns_observed_criterion >2sigma(I) _cod_data_source_file fg1229.cif _cod_data_source_block deneb _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' tag was changed to '_chemical_temperature_decomposition' since the value had been '180 (dec.)'. The value '180 (dec.)' was changed to '180'. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' tag was changed to '_chemical_temperature_decomposition' since the value had been '180 (dec.)'. The value '180 (dec.)' was changed to '180'. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0599P)^2^] where P = (Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0599P)^2^] where P = (Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2006106 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_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 Si .0355(4) .0214(3) .0231(3) -.0008(3) -.0026(3) -.0013(3) C1 .044(2) .049(2) .045(2) .0154(14) .0092(13) .0088(13) C2 .0343(14) .0394(15) .0372(14) .0001(12) -.0023(11) .0100(12) C3 .0369(14) .0276(12) .0214(11) -.0036(11) -.0044(10) -.0010(10) C4 .0360(14) .0245(12) .0177(10) -.0022(10) -.0034(10) -.0051(9) C5 .0397(15) .0257(12) .0224(12) .0040(11) .0024(10) -.0042(10) C6 .043(2) .0298(13) .0219(12) .0004(12) .0095(11) -.0032(10) C7 .057(2) .0294(13) .0164(11) -.0020(12) .0047(11) .0000(10) C8 .043(2) .0311(13) .0227(12) .0007(12) -.0098(11) -.0002(10) C9 .043(2) .041(2) .0408(15) -.0003(13) .0145(12) .0071(12) C10 .045(2) .045(2) .055(2) -.0117(14) .0003(14) .0025(14) C11 .046(2) .0276(13) .0299(13) -.0033(11) -.0050(12) -.0055(11) C12 .059(2) .0239(13) .0231(12) -.0023(12) .0015(12) -.0023(10) C13 .054(2) .0273(13) .0274(13) .0154(13) -.0036(12) -.0013(11) C14 .043(2) .0323(14) .0258(12) .0115(12) .0059(11) -.0039(11) C15 .056(2) .0241(13) .0174(11) .0036(12) .0017(11) -.0012(10) C16 .049(2) .0259(13) .0268(12) .0031(12) -.0096(12) -.0054(10) C17 .053(2) .0313(14) .0323(14) .0052(12) .0030(12) -.0011(11) C18 .053(2) .0318(14) .0338(14) -.0102(12) -.0069(12) -.0031(11) C1' .045(2) .0301(14) .054(2) -.0077(12) -.0037(13) .0097(12) C2' .0321(14) .0381(14) .0351(13) -.0016(12) -.0001(11) .0086(11) C3' .0296(13) .0244(12) .0272(12) .0055(10) -.0022(10) .0075(10) C4' .0312(13) .0166(11) .0266(12) .0019(10) -.0018(10) .0040(9) C5' .0331(14) .0211(11) .0262(12) -.0018(10) .0028(10) .0036(10) C6' .044(2) .0182(11) .0263(12) -.0013(11) -.0044(11) .0007(10) C7' .046(2) .0307(13) .0253(12) .0089(12) .0000(11) -.0027(11) C8' .0363(15) .0360(14) .0291(13) .0113(12) .0037(11) .0039(11) C9' .045(2) .0364(14) .0303(13) -.0044(12) -.0038(12) -.0048(11) C10' .039(2) .044(2) .0350(14) .0041(12) -.0086(12) -.0005(12) C11' .0359(14) .0351(14) .0314(13) .0091(11) -.0051(11) .0081(11) C12' .042(2) .048(2) .0289(13) .0069(13) -.0028(12) .0128(12) C13' .040(2) .045(2) .0397(15) -.0023(13) .0036(13) .0209(13) C14' .045(2) .0217(12) .0433(15) -.0007(11) -.0032(13) .0130(11) C15' .045(2) .0218(12) .0392(14) .0064(11) -.0042(12) .0041(11) C16' .037(2) .0315(14) .0400(14) .0101(12) -.0010(12) .0074(12) 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_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol Si .27173(5) .56860(3) .79170(6) .0268(2) Uani d . 1 . Si C1 .4387(2) .34671(15) .7966(3) .0455(7) Uani d . 1 . C H1A .4658(2) .35096(15) .7111(3) .055 Uiso calc R 1 . H H1B .4839(2) .31643(15) .8520(3) .055 Uiso calc R 1 . H C2 .4298(2) .42868(15) .8563(2) .0371(6) Uani d . 1 . C H2A .4878(2) .43951(15) .9121(2) .045 Uiso calc R 1 . H H2B .4265(2) .46648(15) .7862(2) .045 Uiso calc R 1 . H C3 .3414(2) .43613(13) .9340(2) .0288(5) Uani d . 1 . C C4 .2618(2) .48144(12) .8940(2) .0262(5) Uani d . 1 . C C5 .1716(2) .45895(12) .9329(2) .0293(6) Uani d . 1 . C H5 .1170(2) .48846(12) .9070(2) .035 Uiso calc R 1 . H C6 .1586(2) .39453(13) 1.0085(2) .0313(6) Uani d . 1 . C C7 .2405(2) .36454(13) 1.0703(2) .0343(6) Uani d . 1 . C H7 .2347(2) .32944(13) 1.1383(2) .041 Uiso calc R 1 . H C8 .3306(2) .38529(13) 1.0338(2) .0327(6) Uani d . 1 . C H8 .3860(2) .36451(13) 1.0776(2) .039 Uiso calc R 1 . H C9 .0650(2) .35141(15) 1.0044(2) .0410(7) Uani d . 1 . C H9A .0114(2) .38720(15) .9857(2) .049 Uiso calc R 1 . H H9B .0562(2) .32922(15) 1.0901(2) .049 Uiso calc R 1 . H C10 .0593(2) .2861(2) .9010(3) .0486(7) Uani d . 1 . C H10A .0429(2) .2381(2) .9433(3) .058 Uiso calc R 1 . H H10B .0071(2) .2977(2) .8358(3) .058 Uiso calc R 1 . H C11 .1519(2) .27604(13) .8350(2) .0348(6) Uani d . 1 . C C12 .2258(2) .23146(13) .8867(2) .0355(6) Uani d . 1 . C H12 .2113(2) .19005(13) .9403(2) .043 Uiso calc R 1 . H C13 .3207(2) .24608(13) .8619(2) .0366(6) Uani d . 1 . C H13 .3703(2) .21499(13) .8990(2) .044 Uiso calc R 1 . H C14 .3437(2) .30610(13) .7828(2) .0335(6) Uani d . 1 . C C15 .2681(2) .33848(13) .7093(2) .0324(6) Uani d . 1 . C H15 .2816(2) .37114(13) .6404(2) .039 Uiso calc R 1 . H C16 .1743(2) .32395(13) .7350(2) .0343(6) Uani d . 1 . C H16 .1240(2) .34689(13) .6838(2) .041 Uiso calc R 1 . H C17 .1610(2) .62642(14) .8080(2) .0388(6) Uani d . 1 . C H17A .1693(4) .6759(3) .7678(12) .047 Uiso calc R 1 . H H17B .1496(6) .6333(7) .8991(2) .047 Uiso calc R 1 . H H17C .1059(2) .6004(4) .7655(12) .047 Uiso calc R 1 . H C18 .3750(2) .62484(14) .8620(2) .0400(6) Uani d . 1 . C H18A .4345(2) .5959(4) .8558(13) .048 Uiso calc R 1 . H H18B .3648(5) .6357(7) .9524(4) .048 Uiso calc R 1 . H H18C .3799(7) .6724(4) .8148(9) .048 Uiso calc R 1 . H C1' .3805(2) .69193(14) .5048(3) .0431(7) Uani d . 1 . C H1'1 .3626(2) .72138(14) .5806(3) .052 Uiso calc R 1 . H H1'2 .4279(2) .72198(14) .4593(3) .052 Uiso calc R 1 . H C2' .4291(2) .61538(13) .5521(2) .0352(6) Uani d . 1 . C H2'1 .4852(2) .60493(13) .5006(2) .042 Uiso calc R 1 . H H2'2 .4525(2) .62088(13) .6428(2) .042 Uiso calc R 1 . H C3' .3602(2) .54932(12) .5404(2) .0272(5) Uani d . 1 . C C4' .2817(2) .53918(11) .6189(2) .0249(5) Uani d . 1 . C C5' .2007(2) .50283(12) .5630(2) .0268(5) Uani d . 1 . C H5' .1462(2) .49710(12) .6129(2) .032 Uiso calc R 1 . H C6' .1954(2) .47463(12) .4385(2) .0298(6) Uani d . 1 . C C7' .2814(2) .46850(13) .3793(2) .0340(6) Uani d . 1 . C H7' .2852(2) .43835(13) .3044(2) .041 Uiso calc R 1 . H C8' .3615(2) .50595(13) .4286(2) .0337(6) Uani d . 1 . C H8' .4196(2) .50224(13) .3854(2) .040 Uiso calc R 1 . H C9' .1008(2) .46465(14) .3640(2) .0373(6) Uani d . 1 . C H9'1 .0493(2) .45926(14) .4250(2) .045 Uiso calc R 1 . H H9'2 .1029(2) .41738(14) .3135(2) .045 Uiso calc R 1 . H C10' .0750(2) .53267(14) .2699(2) .0396(6) Uani d . 1 . C H10C .0835(2) .51638(14) .1805(2) .048 Uiso calc R 1 . H H10D .0067(2) .54649(14) .2770(2) .048 Uiso calc R 1 . H C11' .1369(2) .60102(14) .2993(2) .0344(6) Uani d . 1 . C C12' .2206(2) .61319(15) .2353(2) .0398(6) Uani d . 1 . C H12' .2253(2) .59421(15) .1507(2) .048 Uiso calc R 1 . H C13' .2966(2) .65239(15) .2929(2) .0415(7) Uani d . 1 . C H13' .3529(2) .66029(15) .2473(2) .050 Uiso calc R 1 . H C14' .2923(2) .68062(13) .4171(2) .0369(6) Uani d . 1 . C C15' .2016(2) .68358(13) .4669(2) .0354(6) Uani d . 1 . C H15' .1923(2) .71278(13) .5415(2) .043 Uiso calc R 1 . H C16' .1246(2) .64442(13) .4088(2) .0362(6) Uani d . 1 . C H16' .0633(2) .64720(13) .4439(2) .043 Uiso calc R 1 . H 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' Si Si 0.0817 0.0704 '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 C17 Si C18 107.22(12) C17 Si C4 108.10(11) C18 Si C4 106.95(11) C17 Si C4' 109.96(10) C18 Si C4' 115.29(11) C4 Si C4' 109.07(9) C14 C1 C2 112.7(2) C3 C2 C1 111.9(2) C8 C3 C4 118.2(2) C8 C3 C2 118.0(2) C4 C3 C2 122.6(2) C5 C4 C3 117.2(2) C5 C4 Si 119.4(2) C3 C4 Si 123.5(2) C4 C5 C6 122.6(2) C7 C6 C5 116.4(2) C7 C6 C9 120.6(2) C5 C6 C9 122.1(2) C8 C7 C6 120.5(2) C7 C8 C3 121.1(2) C6 C9 C10 113.6(2) C11 C10 C9 112.7(2) C12 C11 C16 116.5(2) C12 C11 C10 121.9(2) C16 C11 C10 120.2(2) C11 C12 C13 121.2(2) C12 C13 C14 120.4(2) C15 C14 C13 116.6(2) C15 C14 C1 119.4(2) C13 C14 C1 122.4(2) C16 C15 C14 121.0(2) C15 C16 C11 121.0(2) C14' C1' C2' 113.4(2) C3' C2' C1' 112.2(2) C8' C3' C4' 117.4(2) C8' C3' C2' 117.0(2) C4' C3' C2' 124.0(2) C5' C4' C3' 116.7(2) C5' C4' Si 115.2(2) C3' C4' Si 128.1(2) C6' C5' C4' 123.8(2) C7' C6' C5' 116.3(2) C7' C6' C9' 121.1(2) C5' C6' C9' 121.7(2) C8' C7' C6' 120.1(2) C7' C8' C3' 122.0(2) C6' C9' C10' 113.3(2) C11' C10' C9' 112.1(2) C12' C11' C16' 116.8(2) C12' C11' C10' 120.8(2) C16' C11' C10' 120.9(2) C13' C12' C11' 120.9(2) C12' C13' C14' 121.1(2) C13' C14' C15' 116.5(2) C13' C14' C1' 122.6(2) C15' C14' C1' 119.7(2) C16' C15' C14' 120.9(2) C15' C16' C11' 120.4(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Si C17 . 1.868(2) ? Si C18 . 1.868(2) ? Si C4 . 1.885(2) ? Si C4' . 1.889(2) ? C1 C14 . 1.507(4) ? C1 C2 . 1.586(4) ? C2 C3 . 1.517(3) ? C3 C8 . 1.391(3) ? C3 C4 . 1.414(3) ? C4 C5 . 1.400(3) ? C5 C6 . 1.404(3) ? C6 C7 . 1.387(3) ? C6 C9 . 1.511(3) ? C7 C8 . 1.381(3) ? C9 C10 . 1.580(4) ? C10 C11 . 1.507(3) ? C11 C12 . 1.384(3) ? C11 C16 . 1.393(3) ? C12 C13 . 1.385(3) ? C13 C14 . 1.393(3) ? C14 C15 . 1.393(3) ? C15 C16 . 1.373(3) ? C1' C14' . 1.506(3) ? C1' C2' . 1.582(3) ? C2' C3' . 1.513(3) ? C3' C8' . 1.397(3) ? C3' C4' . 1.414(3) ? C4' C5' . 1.400(3) ? C5' C6' . 1.390(3) ? C6' C7' . 1.382(3) ? C6' C9' . 1.505(3) ? C7' C8' . 1.375(3) ? C9' C10' . 1.582(3) ? C10' C11' . 1.508(3) ? C11' C12' . 1.392(3) ? C11' C16' . 1.395(3) ? C12' C13' . 1.377(3) ? C13' C14' . 1.393(3) ? C14' C15' . 1.394(3) ? C15' C16' . 1.389(3) ? 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 C14 C1 C2 C3 23.2(3) C1 C2 C3 C8 56.0(3) C1 C2 C3 C4 -110.9(2) C8 C3 C4 C5 -16.4(3) C2 C3 C4 C5 150.5(2) C8 C3 C4 Si 164.1(2) C2 C3 C4 Si -29.0(3) C17 Si C4 C5 18.9(2) C18 Si C4 C5 134.1(2) C4' Si C4 C5 -100.6(2) C17 Si C4 C3 -161.5(2) C18 Si C4 C3 -46.4(2) C4' Si C4 C3 79.0(2) C3 C4 C5 C6 0.1(3) Si C4 C5 C6 179.7(2) C4 C5 C6 C7 15.8(3) C4 C5 C6 C9 -153.3(2) C5 C6 C7 C8 -15.5(3) C9 C6 C7 C8 153.8(2) C6 C7 C8 C3 -0.5(3) C4 C3 C8 C7 16.9(3) C2 C3 C8 C7 -150.5(2) C7 C6 C9 C10 -78.7(3) C5 C6 C9 C10 90.0(3) C6 C9 C10 C11 4.8(3) C9 C10 C11 C12 85.4(3) C9 C10 C11 C16 -80.5(3) C16 C11 C12 C13 14.6(3) C10 C11 C12 C13 -151.8(2) C11 C12 C13 C14 -0.6(3) C12 C13 C14 C15 -13.9(3) C12 C13 C14 C1 152.0(2) C2 C1 C14 C15 58.2(3) C2 C1 C14 C13 -107.3(3) C13 C14 C15 C16 14.4(3) C1 C14 C15 C16 -152.0(2) C14 C15 C16 C11 -0.3(3) C12 C11 C16 C15 -14.2(3) C10 C11 C16 C15 152.5(2) C14' C1' C2' C3' -20.7(3) C1' C2' C3' C8' 94.4(3) C1' C2' C3' C4' -70.7(3) C8' C3' C4' C5' -16.6(3) C2' C3' C4' C5' 148.5(2) C8' C3' C4' Si 163.4(2) C2' C3' C4' Si -31.6(3) C17 Si C4' C5' -53.3(2) C18 Si C4' C5' -174.6(2) C4 Si C4' C5' 65.1(2) C17 Si C4' C3' 126.7(2) C18 Si C4' C3' 5.4(2) C4 Si C4' C3' -114.9(2) C3' C4' C5' C6' 2.3(3) Si C4' C5' C6' -177.6(2) C4' C5' C6' C7' 14.1(3) C4' C5' C6' C9' -155.2(2) C5' C6' C7' C8' -15.9(3) C9' C6' C7' C8' 153.5(2) C6' C7' C8' C3' 1.7(3) C4' C3' C8' C7' 15.1(3) C2' C3' C8' C7' -151.0(2) C7' C6' C9' C10' -71.6(3) C5' C6' C9' C10' 97.2(3) C6' C9' C10' C11' -14.7(3) C9' C10' C11' C12' 94.0(3) C9' C10' C11' C16' -71.7(3) C16' C11' C12' C13' 14.7(3) C10' C11' C12' C13' -151.6(2) C11' C12' C13' C14' 0.4(4) C12' C13' C14' C15' -15.0(3) C12' C13' C14' C1' 152.1(2) C2' C1' C14' C13' -69.5(3) C2' C1' C14' C15' 97.3(3) C13' C14' C15' C16' 14.7(3) C1' C14' C15' C16' -152.9(2) C14' C15' C16' C11' 0.2(3) C12' C11' C16' C15' -14.9(3) C10' C11' C16' C15' 151.3(2) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 9013501 2 PubChem 10838202