#------------------------------------------------------------------------------ #$Date: 2025-08-19 12:52:15 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301804 $ #$URL: svn://www.crystallography.net/cod/cif/2/21/45/2214553.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_2214553 loop_ _publ_author_name 'Sema \"Ozt\"urk Y\?ild\?ir\?im' 'Mehmet Akkurt' 'Ali Asghar Jarrahpour' 'Shadab Rezaei' 'Frank W. Heinemann' _publ_section_title N-(2-{[(1E)-1-(2-Hydroxyphenyl)ethylidene]amino}phenyl)-2-methoxyacetamide _journal_coeditor_code BT2432 _journal_issue 8 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3478 _journal_page_last o3479 _journal_paper_doi 10.1107/S1600536807033673 _journal_volume 63 _journal_year 2007 _chemical_formula_iupac 'C17 H18 N2 O3' _chemical_formula_moiety 'C17 H18 N2 O3' _chemical_formula_sum 'C17 H18 N2 O3' _chemical_formula_weight 298.33 _chemical_name_systematic ; N-(2-{[(1E)-1-(2-Hydroxyphenyl)ethylidene]amino}phenyl)-2-methoxyacetamide ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 98.988(8) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.4061(8) _cell_length_b 11.2568(5) _cell_length_c 16.4145(16) _cell_measurement_reflns_used 117 _cell_measurement_temperature 200 _cell_measurement_theta_max 20 _cell_measurement_theta_min 6 _cell_volume 1534.2(2) _computing_cell_refinement 'EVALCCD (Duisenberg et al., 2003)' _computing_data_collection 'COLLECT (Nonius, 1999)' _computing_data_reduction 'SADABS (Sheldrick, 2002)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'PLATON (Spek, 2003)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994) or SIR97 (Altomare et al., 1999)' _diffrn_ambient_temperature 200 _diffrn_detector_area_resol_mean 9 _diffrn_measured_fraction_theta_full 0.984 _diffrn_measured_fraction_theta_max 0.984 _diffrn_measurement_device_type 'Bruker--Nonius KappaCCD' _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 0.0519 _diffrn_reflns_av_sigmaI/netI 0.0294 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 35768 _diffrn_reflns_reduction_process ; ; _diffrn_reflns_theta_full 28.50 _diffrn_reflns_theta_max 28.50 _diffrn_reflns_theta_min 3.62 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_correction_T_min 0.981 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2002)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_description prism _exptl_crystal_F_000 632 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.13 _refine_diff_density_max 0.195 _refine_diff_density_min -0.214 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 209 _refine_ls_number_reflns 3829 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.010 _refine_ls_R_factor_all 0.0676 _refine_ls_R_factor_gt 0.0410 _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^)+(0.043P)^2^+0.3845P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0869 _refine_ls_wR_factor_ref 0.0985 _reflns_number_gt 2752 _reflns_number_total 3829 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bt2432.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2214553 _cod_database_fobs_code 2214553 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2+y,1/2-z 3 -x,-y,-z 4 1/2+x,1/2-y,1/2+z 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 O1 0.0692(7) 0.0355(5) 0.0276(5) 0.0188(5) 0.0114(5) 0.0043(4) O2 0.0296(5) 0.0552(6) 0.0349(5) 0.0067(4) 0.0116(4) -0.0097(5) O3 0.0303(5) 0.0412(5) 0.0378(5) 0.0025(4) 0.0030(4) -0.0139(4) N1 0.0239(5) 0.0313(6) 0.0255(5) 0.0042(4) 0.0076(4) -0.0011(4) N2 0.0235(5) 0.0273(5) 0.0239(5) 0.0010(4) 0.0071(4) -0.0042(4) C1 0.0280(6) 0.0275(6) 0.0292(6) 0.0000(5) 0.0077(5) 0.0014(5) C2 0.0374(7) 0.0363(7) 0.0258(6) -0.0045(6) 0.0076(5) -0.0015(5) C3 0.0500(8) 0.0310(7) 0.0386(8) -0.0077(6) 0.0199(6) -0.0099(6) C4 0.0867(13) 0.0264(7) 0.0508(9) 0.0102(7) 0.0275(9) 0.0020(7) C5 0.0708(11) 0.0308(7) 0.0354(8) 0.0116(7) 0.0176(7) 0.0069(6) C6 0.0283(6) 0.0279(6) 0.0282(6) 0.0009(5) 0.0089(5) 0.0017(5) C7 0.0252(6) 0.0308(6) 0.0265(6) 0.0016(5) 0.0076(5) 0.0025(5) C8 0.0662(10) 0.0382(8) 0.0279(7) 0.0095(7) 0.0105(7) 0.0051(6) C9 0.0274(6) 0.0271(6) 0.0219(6) 0.0012(5) 0.0079(5) 0.0022(5) C10 0.0242(6) 0.0405(7) 0.0329(7) 0.0016(5) 0.0058(5) 0.0022(6) C11 0.0319(7) 0.0410(7) 0.0295(7) -0.0069(6) 0.0008(5) -0.0009(6) C12 0.0412(7) 0.0298(6) 0.0242(6) -0.0034(6) 0.0055(5) -0.0030(5) C13 0.0317(6) 0.0261(6) 0.0241(6) 0.0021(5) 0.0092(5) 0.0008(5) C14 0.0253(6) 0.0238(6) 0.0207(5) -0.0009(5) 0.0065(4) 0.0033(4) C15 0.0247(6) 0.0267(6) 0.0287(6) 0.0029(5) 0.0072(5) 0.0028(5) C16 0.0247(6) 0.0364(7) 0.0363(7) 0.0004(5) 0.0061(5) -0.0041(6) C17 0.0466(9) 0.0687(12) 0.0525(10) 0.0002(8) -0.0036(8) -0.0286(9) 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_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy O O1 0.38697(14) 0.26077(9) 0.65758(6) 0.0437(3) Uani . . 1.000 O O2 0.86553(11) 0.07956(9) 0.42532(6) 0.0392(3) Uani . . 1.000 O O3 0.83793(11) 0.24633(9) 0.60472(6) 0.0367(3) Uani . . 1.000 N N1 0.36411(12) 0.24204(9) 0.50114(6) 0.0265(3) Uani . . 1.000 N N2 0.65482(12) 0.14390(9) 0.48630(6) 0.0245(3) Uani . . 1.000 C C1 0.33574(15) 0.37372(11) 0.64393(8) 0.0279(3) Uani . . 1.000 C C2 0.31560(16) 0.44167(12) 0.71259(8) 0.0329(4) Uani . . 1.000 C C3 0.26040(18) 0.55646(12) 0.70294(9) 0.0385(4) Uani . . 1.000 C C4 0.2252(2) 0.60576(14) 0.62526(10) 0.0528(6) Uani . . 1.000 C C5 0.2461(2) 0.53965(13) 0.55684(9) 0.0447(5) Uani . . 1.000 C C6 0.30137(15) 0.42201(11) 0.56370(7) 0.0277(3) Uani . . 1.000 C C7 0.31783(15) 0.35103(11) 0.48987(7) 0.0271(3) Uani . . 1.000 C C8 0.2818(2) 0.40854(13) 0.40636(8) 0.0438(5) Uani . . 1.000 C C9 0.37200(14) 0.16073(11) 0.43574(7) 0.0250(3) Uani . . 1.000 C C10 0.23477(15) 0.12373(12) 0.38351(8) 0.0324(4) Uani . . 1.000 C C11 0.24396(16) 0.03598(13) 0.32547(8) 0.0346(4) Uani . . 1.000 C C12 0.39076(17) -0.01639(12) 0.31929(8) 0.0317(4) Uani . . 1.000 C C13 0.52882(15) 0.01923(11) 0.37099(7) 0.0268(3) Uani . . 1.000 C C14 0.52055(14) 0.10719(10) 0.42966(7) 0.0230(3) Uani . . 1.000 C C15 0.81256(14) 0.12812(11) 0.48183(8) 0.0264(3) Uani . . 1.000 C C16 0.92509(15) 0.17935(12) 0.55424(8) 0.0323(4) Uani . . 1.000 C C17 0.9274(2) 0.27786(17) 0.68146(11) 0.0571(6) Uani . . 1.000 H HO1 0.386(2) 0.2308(16) 0.6071(12) 0.061(5) Uiso . . 1.000 H H2 0.33960 0.40910 0.76520 0.0390 Uiso calc R 1.000 H HN1 0.6372(17) 0.1835(13) 0.5286(9) 0.030(4) Uiso . . 1.000 H H3 0.24670 0.60120 0.74900 0.0460 Uiso calc R 1.000 H H4 0.18740 0.68340 0.61900 0.0630 Uiso calc R 1.000 H H5 0.22290 0.57410 0.50480 0.0540 Uiso calc R 1.000 H H8A 0.31510 0.35680 0.36570 0.0660 Uiso calc R 1.000 H H8B 0.33900 0.48240 0.40700 0.0660 Uiso calc R 1.000 H H8C 0.16820 0.42320 0.39300 0.0660 Uiso calc R 1.000 H H10 0.13580 0.15830 0.38760 0.0390 Uiso calc R 1.000 H H11 0.15160 0.01210 0.29060 0.0410 Uiso calc R 1.000 H H12 0.39660 -0.07560 0.28030 0.0380 Uiso calc R 1.000 H H13 0.62730 -0.01580 0.36640 0.0320 Uiso calc R 1.000 H H16A 0.98160 0.11540 0.58620 0.0390 Uiso calc R 1.000 H H16B 1.00440 0.22960 0.53420 0.0390 Uiso calc R 1.000 H H17A 0.97260 0.20770 0.70920 0.0860 Uiso calc R 1.000 H H17B 0.85800 0.31640 0.71450 0.0860 Uiso calc R 1.000 H H17C 1.01260 0.33100 0.67300 0.0860 Uiso calc R 1.000 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 '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 C16 O3 C17 114.03(11) no C1 O1 HO1 104.2(12) no C7 N1 C9 123.54(10) no C14 N2 C15 128.17(10) no C15 N2 HN1 114.1(10) no C14 N2 HN1 117.7(10) no O1 C1 C6 122.06(11) no O1 C1 C2 117.29(12) no C2 C1 C6 120.64(12) no C1 C2 C3 120.29(12) no C2 C3 C4 120.31(13) no C3 C4 C5 119.91(14) no C4 C5 C6 121.75(13) no C1 C6 C7 121.70(11) no C1 C6 C5 117.09(11) no C5 C6 C7 121.18(11) no N1 C7 C6 117.48(10) no N1 C7 C8 123.57(11) no C6 C7 C8 118.96(11) no C10 C9 C14 119.30(11) no N1 C9 C14 118.52(10) no N1 C9 C10 121.83(11) no C9 C10 C11 120.59(12) no C10 C11 C12 120.04(12) no C11 C12 C13 120.16(12) no C12 C13 C14 120.17(12) no C9 C14 C13 119.74(11) no N2 C14 C9 117.21(10) no N2 C14 C13 123.01(11) no O2 C15 N2 125.34(12) no O2 C15 C16 120.72(11) no N2 C15 C16 113.94(11) no O3 C16 C15 110.34(10) no C1 C2 H2 120.00 no C3 C2 H2 120.00 no C2 C3 H3 120.00 no C4 C3 H3 120.00 no C3 C4 H4 120.00 no C5 C4 H4 120.00 no C4 C5 H5 119.00 no C6 C5 H5 119.00 no C7 C8 H8A 109.00 no C7 C8 H8B 110.00 no C7 C8 H8C 109.00 no H8A C8 H8B 109.00 no H8A C8 H8C 109.00 no H8B C8 H8C 109.00 no C9 C10 H10 120.00 no C11 C10 H10 120.00 no C10 C11 H11 120.00 no C12 C11 H11 120.00 no C11 C12 H12 120.00 no C13 C12 H12 120.00 no C12 C13 H13 120.00 no C14 C13 H13 120.00 no O3 C16 H16A 110.00 no O3 C16 H16B 110.00 no C15 C16 H16A 110.00 no C15 C16 H16B 110.00 no H16A C16 H16B 108.00 no O3 C17 H17A 109.00 no O3 C17 H17B 109.00 no O3 C17 H17C 110.00 no H17A C17 H17B 110.00 no H17A C17 H17C 109.00 no H17B C17 H17C 109.00 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 1.3499(16) no O2 C15 1.2192(16) no O3 C16 1.4077(16) no O3 C17 1.408(2) no O1 HO1 0.894(19) no N1 C7 1.2916(16) no N1 C9 1.4202(15) no N2 C14 1.4076(15) no N2 C15 1.3511(16) no N2 HN1 0.857(15) no C1 C6 1.4122(17) no C1 C2 1.3941(18) no C2 C3 1.3737(19) no C3 C4 1.380(2) no C4 C5 1.381(2) no C5 C6 1.4021(19) no C6 C7 1.4760(17) no C7 C8 1.5034(18) no C9 C14 1.4041(17) no C9 C10 1.3893(18) no C10 C11 1.3829(19) no C11 C12 1.386(2) no C12 C13 1.3857(19) no C13 C14 1.3905(16) no C15 C16 1.5129(18) no C2 H2 0.9300 no C3 H3 0.9300 no C4 H4 0.9300 no C5 H5 0.9300 no C8 H8A 0.9600 no C8 H8B 0.9600 no C8 H8C 0.9600 no C10 H10 0.9300 no C11 H11 0.9300 no C12 H12 0.9300 no C13 H13 0.9300 no C16 H16A 0.9700 no C16 H16B 0.9700 no C17 H17A 0.9600 no C17 H17B 0.9600 no C17 H17C 0.9600 no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 N1 2.5537(14) . no O1 C12 3.3138(18) 3_656 no O1 C13 3.2801(16) 3_656 no O2 C13 2.9119(16) . no O2 C16 3.3941(17) 3_756 no O2 C10 3.3193(16) 1_655 no O3 N2 2.5578(14) . no O1 H3 2.7200 2_546 no O1 H13 2.7900 3_656 no O1 H12 2.8500 3_656 no O2 H13 2.3400 . no O2 H10 2.6000 1_655 no O2 H16A 2.5700 3_756 no O2 H2 2.6100 4_554 no O2 H4 2.7800 3_666 no O3 HN1 2.062(15) . no O3 H5 2.7000 3_666 no N1 O1 2.5537(14) . no N1 N2 2.7272(15) . no N2 N1 2.7272(15) . no N2 O3 2.5578(14) . no N1 HN1 2.363(15) . no N1 HO1 1.725(19) . no C4 C15 3.463(2) 3_666 no C8 C10 3.245(2) . no C10 C8 3.245(2) . no C10 O2 3.3193(16) 1_455 no C11 C16 3.5595(19) 3_656 no C12 O1 3.3138(18) 3_656 no C12 C17 3.555(2) 4_454 no C13 O2 2.9119(16) . no C13 O1 3.2801(16) 3_656 no C14 C14 3.3948(16) 3_656 no C15 C4 3.463(2) 3_666 no C16 O2 3.3941(17) 3_756 no C16 C11 3.5595(19) 3_656 no C17 C12 3.555(2) 4_555 no C1 H17C 2.8700 1_455 no C2 H17C 2.8200 1_455 no C2 H11 2.9600 4_555 no C3 H17A 3.0000 2_656 no C3 H13 3.1000 4_455 no C5 H8C 2.9700 . no C5 H8B 2.7700 . no C7 HO1 2.349(19) . no C7 H10 3.0100 . no C8 H10 3.0700 . no C8 H5 2.5700 . no C9 HO1 2.906(19) . no C9 H8A 2.5000 . no C10 H8A 2.7400 . no C11 H17B 2.7500 4_454 no C11 H16A 3.0800 3_656 no C12 H17B 2.8200 4_454 no C13 HO1 2.913(18) 3_656 no C15 H13 2.7800 . no C15 H4 2.6900 3_666 no HO1 N1 1.725(19) . no HO1 C7 2.349(19) . no HO1 C9 2.906(19) . no HO1 C13 2.913(18) 3_656 no HO1 H13 2.4600 3_656 no H2 O2 2.6100 4_455 no HN1 O3 2.062(15) . no HN1 N1 2.363(15) . no H3 O1 2.7200 2_556 no H3 H13 2.5000 4_455 no H4 O2 2.7800 3_666 no H4 C15 2.6900 3_666 no H5 C8 2.5700 . no H5 H8B 2.2500 . no H5 H8C 2.4900 . no H5 O3 2.7000 3_666 no H8A C9 2.5000 . no H8A C10 2.7400 . no H8B C5 2.7700 . no H8B H5 2.2500 . no H8C C5 2.9700 . no H8C H5 2.4900 . no H10 O2 2.6000 1_455 no H10 C7 3.0100 . no H10 C8 3.0700 . no H11 C2 2.9600 4_454 no H12 O1 2.8500 3_656 no H13 O2 2.3400 . no H13 C15 2.7800 . no H13 O1 2.7900 3_656 no H13 HO1 2.4600 3_656 no H13 C3 3.1000 4_554 no H13 H3 2.5000 4_554 no H16A H17A 2.2800 . no H16A O2 2.5700 3_756 no H16A C11 3.0800 3_656 no H16B H17C 2.5400 . no H17A H16A 2.2800 . no H17A C3 3.0000 2_646 no H17B C11 2.7500 4_555 no H17B C12 2.8200 4_555 no H17C C1 2.8700 1_655 no H17C C2 2.8200 1_655 no H17C H16B 2.5400 . 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 O1 HO1 N1 . 0.894(19) 1.725(19) 2.5537(14) 153.1(17) yes N2 HN1 O3 . 0.857(15) 2.062(15) 2.5578(14) 116.2(12) yes N2 HN1 N1 . 0.857(15) 2.363(15) 2.7272(15) 106.0(11) yes C13 H13 O2 . 0.93 2.34 2.9119(16) 119 yes C16 H16A O2 3_756 0.97 2.57 3.3941(17) 143 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 C17 O3 C16 C15 168.27(12) no C9 N1 C7 C6 174.48(11) no C9 N1 C7 C8 -6.1(2) no C7 N1 C9 C14 121.72(13) no C7 N1 C9 C10 -65.16(17) no C14 N2 C15 C16 -179.91(11) no C14 N2 C15 O2 1.3(2) no C15 N2 C14 C9 -163.09(12) no C15 N2 C14 C13 18.93(19) no C2 C1 C6 C7 -178.46(12) no C2 C1 C6 C5 -0.31(19) no O1 C1 C6 C7 0.7(2) no O1 C1 C6 C5 178.85(13) no O1 C1 C2 C3 -178.57(13) no C6 C1 C2 C3 0.6(2) no C1 C2 C3 C4 -0.3(2) no C2 C3 C4 C5 -0.3(2) no C3 C4 C5 C6 0.6(3) no C4 C5 C6 C1 -0.3(2) no C4 C5 C6 C7 177.87(14) no C5 C6 C7 N1 -177.62(13) no C1 C6 C7 C8 -179.04(13) no C1 C6 C7 N1 0.45(18) no C5 C6 C7 C8 2.9(2) no C14 C9 C10 C11 -0.65(19) no N1 C9 C14 C13 174.11(11) no N1 C9 C10 C11 -173.72(12) no C10 C9 C14 N2 -177.24(11) no C10 C9 C14 C13 0.81(18) no N1 C9 C14 N2 -3.95(16) no C9 C10 C11 C12 0.4(2) no C10 C11 C12 C13 -0.2(2) no C11 C12 C13 C14 0.39(19) no C12 C13 C14 N2 177.25(11) no C12 C13 C14 C9 -0.69(18) no O2 C15 C16 O3 170.90(12) no N2 C15 C16 O3 -7.92(15) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21184634 2 PubChem 139072633