#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/54/4025401.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4025401
loop_
_publ_author_name
'Maialen Aginagalde'
'Yosu Vara'
'Ana Arrieta'
'Ronen Zangi'
'Vicente L. Cebolla'
'Arantzazu Delgado-Camón'
'Fernando P. Cossío'
_publ_section_title
;
 Tandem [8 + 2] Cycloaddition-[2 + 6 + 2] Dehydrogenation Reactions
 Involving Imidazo[1,2-a]pyridines and Imidazo[1,2-a]pyrimidines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2776
_journal_page_last               2784
_journal_paper_doi               10.1021/jo9022815
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration unk
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C20 H14 N2 O1'
_chemical_formula_sum            'C20 H14 N2 O'
_chemical_formula_weight         298.33
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2008-07-17T12:17:35-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;

2008-07-17 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2180(2)
_cell_length_b                   13.0241(4)
_cell_length_c                   18.1587(6)
_cell_measurement_reflns_used    4749
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.5043
_cell_measurement_theta_min      3.1252
_cell_measurement_wavelength     0.71073
_cell_volume                     1470.56(8)
_computing_cell_refinement
;

        CrysAlis RED, Oxford Diffraction Ltd.,

        Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)

        (compiled Jan 10 2008,16:37:18)

;
_computing_data_collection
;

        CrysAlis CCD, Oxford Diffraction Ltd.,

        Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)

        (compiled Jan 10 2008,16:37:18)

;
_computing_data_reduction
;

        CrysAlis RED, Oxford Diffraction Ltd.,

        Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)

        (compiled Jan 10 2008,16:37:18)

;
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 (Giacovazzo et al, 2004)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 8.3504
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;


  1 omega  -29.00   23.00   1.0000   30.0000

omega____ theta____ kappa____ phi______ omega'___ theta'___ frames

    -      -26.3472   45.0000  300.0000    0.0000    0.0000 52




  2 omega  -75.00  -25.00   1.0000   30.0000

omega____ theta____ kappa____ phi______ omega'___ theta'___ frames

    -      -26.3472   45.0000  210.0000    0.0000    0.0000 50




  3 omega  -22.00   75.00   1.0000   30.0000

omega____ theta____ kappa____ phi______ omega'___ theta'___ frames

    -       26.8159   45.0000  330.0000    0.0000    0.0000 97




  4 omega  -55.00   73.00   1.0000   30.0000

omega____ theta____ kappa____ phi______ omega'___ theta'___ frames

    -       26.8159  -45.0000  150.0000    0.0000    0.0000 128




  5 omega  -20.00    6.00   1.0000   30.0000

omega____ theta____ kappa____ phi______ omega'___ theta'___ frames

    -       26.8159   77.0000  210.0000    0.0000    0.0000 26




  6 omega  -75.00  -23.00   1.0000   30.0000

omega____ theta____ kappa____ phi______ omega'___ theta'___ frames

    -       26.8159  -77.0000  270.0000    0.0000    0.0000 52




  7 omega   27.00   75.00   1.0000   30.0000

omega____ theta____ kappa____ phi______ omega'___ theta'___ frames

    -       26.8159  -45.0000  240.0000    0.0000    0.0000 48




  8 omega  -67.00  -17.00   1.0000   30.0000

omega____ theta____ kappa____ phi______ omega'___ theta'___ frames

    -       26.8159  -45.0000  300.0000    0.0000    0.0000 50




  9 omega  -67.00  -42.00   1.0000   30.0000

omega____ theta____ kappa____ phi______ omega'___ theta'___ frames

    -       26.8159  -45.0000  120.0000    0.0000    0.0000 25




 10 omega   50.00  108.00   1.0000   30.0000

omega____ theta____ kappa____ phi______ omega'___ theta'___ frames

    -       26.8159   45.0000  180.0000    0.0000    0.0000 58



;
_diffrn_orient_matrix_UB_11      0.0722774103
_diffrn_orient_matrix_UB_12      -0.0249061836
_diffrn_orient_matrix_UB_13      0.0242618958
_diffrn_orient_matrix_UB_21      -0.0522623831
_diffrn_orient_matrix_UB_22      0.0230784493
_diffrn_orient_matrix_UB_23      0.0304406592
_diffrn_orient_matrix_UB_31      -0.0708222913
_diffrn_orient_matrix_UB_32      -0.0424546074
_diffrn_orient_matrix_UB_33      0.0023087852
_diffrn_radiation_collimation    '1.0 mm diameter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.035
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12841
_diffrn_reflns_theta_full        26.5
_diffrn_reflns_theta_max         26.5
_diffrn_reflns_theta_min         3.13
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;

        CrysAlis RED, Oxford Diffraction Ltd.,

        Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)

        (compiled Jan 10 2008,16:37:18)

Analytical numeric absorption correction using a multifaceted crystal

                        model based on expressions derived by R.C. Clark & J.S.

        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)

;
_exptl_crystal_colour            'dark orange'
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.8088
_exptl_crystal_size_mid          0.1875
_exptl_crystal_size_min          0.1008
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         1777
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.972
_refine_ls_R_factor_all          0.066
_refine_ls_R_factor_gt           0.0479
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0842P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1212
_reflns_number_gt                1306
_reflns_number_total             1777
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9022815_si_001.cif
_cod_data_source_block           macro11
_cod_original_formula_sum        'C20 H14 N2 O1'
_cod_database_code               4025401
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'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.0437(4) 0.5276(2) 0.39450(14) 0.0460(7) Uani 1 1 d . . .
C3 C -0.1011(4) 0.5419(2) 0.45408(14) 0.0415(6) Uani 1 1 d . . .
C4 C -0.1831(5) 0.52447(19) 0.52746(14) 0.0443(7) Uani 1 1 d . . .
C5 C -0.3801(5) 0.5807(2) 0.53456(15) 0.0490(7) Uani 1 1 d . . .
C6 C -0.4175(4) 0.6356(2) 0.46645(16) 0.0458(7) Uani 1 1 d . . .
C7 C -0.5555(5) 0.7034(2) 0.43421(18) 0.0578(8) Uani 1 1 d . . .
H7 H -0.6766 0.7263 0.4594 0.069 Uiso 1 1 calc R . .
C8 C -0.5128(5) 0.7380(2) 0.36290(18) 0.0592(8) Uani 1 1 d . . .
H8 H -0.6074 0.7847 0.3417 0.071 Uiso 1 1 calc R . .
C9 C -0.3370(5) 0.7064(2) 0.32228(17) 0.0558(8) Uani 1 1 d . . .
H9 H -0.3148 0.7308 0.2747 0.067 Uiso 1 1 calc R . .
C10 C -0.1944(5) 0.6375(2) 0.35395(15) 0.0457(7) Uani 1 1 d . . .
C11 C -0.1078(6) 0.4685(2) 0.58757(15) 0.0561(8) Uani 1 1 d . . .
H11 H 0.0203 0.4319 0.5846 0.067 Uiso 1 1 calc R . .
C12 C -0.2273(6) 0.4688(2) 0.65146(16) 0.0664(9) Uani 1 1 d . . .
H12 H -0.178 0.4316 0.6918 0.08 Uiso 1 1 calc R . .
C13 C -0.4173(6) 0.5224(2) 0.65762(19) 0.0704(10) Uani 1 1 d . . .
H13 H -0.4938 0.5201 0.7016 0.085 Uiso 1 1 calc R . .
C14 C -0.4952(6) 0.5787(2) 0.60008(17) 0.0606(9) Uani 1 1 d . . .
H14 H -0.6231 0.6151 0.6047 0.073 Uiso 1 1 calc R . .
C15 C 0.2316(4) 0.46013(18) 0.39028(15) 0.0423(6) Uani 1 1 d . . .
C16 C 0.2786(5) 0.3935(2) 0.44781(16) 0.0618(9) Uani 1 1 d . . .
H16 H 0.1908 0.3929 0.4893 0.074 Uiso 1 1 calc R . .
C17 C 0.4534(6) 0.3280(3) 0.44468(18) 0.0672(9) Uani 1 1 d . . .
H17 H 0.4827 0.2842 0.4839 0.081 Uiso 1 1 calc R . .
C18 C 0.5829(5) 0.3276(2) 0.38411(18) 0.0520(7) Uani 1 1 d . . .
C19 C 0.5405(5) 0.3926(2) 0.32717(16) 0.0524(7) Uani 1 1 d . . .
H19 H 0.6289 0.3926 0.2859 0.063 Uiso 1 1 calc R . .
C20 C 0.3665(4) 0.4585(2) 0.33058(15) 0.0488(7) Uani 1 1 d . . .
H20 H 0.3402 0.5027 0.2914 0.059 Uiso 1 1 calc R . .
C21 C 0.8838(5) 0.2516(3) 0.32353(19) 0.0751(10) Uani 1 1 d . . .
H21A H 0.9323 0.3186 0.309 0.113 Uiso 1 1 calc R . .
H21B H 0.8035 0.2211 0.284 0.113 Uiso 1 1 calc R . .
H21C H 1.0057 0.2092 0.3349 0.113 Uiso 1 1 calc R . .
N1 N -0.0131(4) 0.58635(18) 0.33468(12) 0.0522(6) Uani 1 1 d . . .
N2 N -0.2443(4) 0.60921(16) 0.42400(12) 0.0449(6) Uani 1 1 d . . .
O1 O 0.7519(4) 0.26015(17) 0.38609(13) 0.0778(7) Uani 1 1 d . . .
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 0 '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 0.006 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C2 C3 111.5(2) . . ?
N1 C2 C15 119.9(2) . . ?
C3 C2 C15 128.7(2) . . ?
N2 C3 C2 101.2(2) . . ?
N2 C3 C4 103.9(2) . . ?
C2 C3 C4 154.9(3) . . ?
C11 C4 C5 118.9(3) . . ?
C11 C4 C3 133.3(3) . . ?
C5 C4 C3 107.7(2) . . ?
C14 C5 C4 120.5(3) . . ?
C14 C5 C6 131.2(3) . . ?
C4 C5 C6 108.2(2) . . ?
C7 C6 N2 114.6(3) . . ?
C7 C6 C5 142.0(3) . . ?
N2 C6 C5 103.4(2) . . ?
C6 C7 C8 119.2(3) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C9 C8 C7 123.3(3) . . ?
C9 C8 H8 118.3 . . ?
C7 C8 H8 118.3 . . ?
C8 C9 C10 118.5(3) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 H9 120.7 . . ?
N1 C10 N2 107.3(2) . . ?
N1 C10 C9 138.0(3) . . ?
N2 C10 C9 114.7(3) . . ?
C12 C11 C4 118.5(3) . . ?
C12 C11 H11 120.8 . . ?
C4 C11 H11 120.8 . . ?
C13 C12 C11 122.2(3) . . ?
C13 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
C14 C13 C12 121.0(3) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C5 118.9(3) . . ?
C13 C14 H14 120.6 . . ?
C5 C14 H14 120.6 . . ?
C20 C15 C16 117.1(2) . . ?
C20 C15 C2 122.6(2) . . ?
C16 C15 C2 120.2(2) . . ?
C17 C16 C15 121.3(3) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C18 C17 C16 120.0(3) . . ?
C18 C17 H17 120 . . ?
C16 C17 H17 120 . . ?
C19 C18 C17 119.8(3) . . ?
C19 C18 O1 124.5(3) . . ?
C17 C18 O1 115.7(3) . . ?
C18 C19 C20 120.2(3) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C15 C20 C19 121.6(3) . . ?
C15 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
O1 C21 H21A 109.5 . . ?
O1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C10 N1 C2 106.5(2) . . ?
C10 N2 C3 113.6(2) . . ?
C10 N2 C6 129.7(3) . . ?
C3 N2 C6 116.7(2) . . ?
C18 O1 C21 118.5(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 N1 1.375(3) . ?
C2 C3 1.420(4) . ?
C2 C15 1.464(4) . ?
C3 N2 1.363(3) . ?
C3 C4 1.445(4) . ?
C4 C11 1.393(4) . ?
C4 C5 1.433(4) . ?
C5 C14 1.389(4) . ?
C5 C6 1.447(4) . ?
C6 C7 1.363(4) . ?
C6 N2 1.368(3) . ?
C7 C8 1.397(4) . ?
C7 H7 0.93 . ?
C8 C9 1.381(4) . ?
C8 H8 0.93 . ?
C9 C10 1.386(4) . ?
C9 H9 0.93 . ?
C10 N1 1.355(4) . ?
C10 N2 1.360(3) . ?
C11 C12 1.378(4) . ?
C11 H11 0.93 . ?
C12 C13 1.377(5) . ?
C12 H12 0.93 . ?
C13 C14 1.366(5) . ?
C13 H13 0.93 . ?
C14 H14 0.93 . ?
C15 C20 1.371(4) . ?
C15 C16 1.390(4) . ?
C16 C17 1.383(4) . ?
C16 H16 0.93 . ?
C17 C18 1.363(4) . ?
C17 H17 0.93 . ?
C18 C19 1.362(4) . ?
C18 O1 1.370(3) . ?
C19 C20 1.382(4) . ?
C19 H19 0.93 . ?
C20 H20 0.93 . ?
C21 O1 1.406(4) . ?
C21 H21A 0.96 . ?
C21 H21B 0.96 . ?
C21 H21C 0.96 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C20 H20 N1 0.9300 2.5700 2.890(4) 100.00 . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 N2 1.6(3) . . . . ?
C15 C2 C3 N2 -177.4(3) . . . . ?
N1 C2 C3 C4 179.7(5) . . . . ?
C15 C2 C3 C4 0.8(7) . . . . ?
N2 C3 C4 C11 -176.1(3) . . . . ?
C2 C3 C4 C11 5.7(8) . . . . ?
N2 C3 C4 C5 2.7(3) . . . . ?
C2 C3 C4 C5 -175.5(5) . . . . ?
C11 C4 C5 C14 -0.6(4) . . . . ?
C3 C4 C5 C14 -179.6(2) . . . . ?
C11 C4 C5 C6 177.3(2) . . . . ?
C3 C4 C5 C6 -1.7(3) . . . . ?
C14 C5 C6 C7 1.0(6) . . . . ?
C4 C5 C6 C7 -176.7(3) . . . . ?
C14 C5 C6 N2 177.6(3) . . . . ?
C4 C5 C6 N2 0.0(3) . . . . ?
N2 C6 C7 C8 0.9(4) . . . . ?
C5 C6 C7 C8 177.4(3) . . . . ?
C6 C7 C8 C9 0.6(4) . . . . ?
C7 C8 C9 C10 -0.6(4) . . . . ?
C8 C9 C10 N1 177.8(3) . . . . ?
C8 C9 C10 N2 -0.9(4) . . . . ?
C5 C4 C11 C12 0.6(4) . . . . ?
C3 C4 C11 C12 179.3(3) . . . . ?
C4 C11 C12 C13 -0.1(5) . . . . ?
C11 C12 C13 C14 -0.5(5) . . . . ?
C12 C13 C14 C5 0.5(5) . . . . ?
C4 C5 C14 C13 0.1(4) . . . . ?
C6 C5 C14 C13 -177.3(3) . . . . ?
N1 C2 C15 C20 5.4(4) . . . . ?
C3 C2 C15 C20 -175.8(3) . . . . ?
N1 C2 C15 C16 -174.0(3) . . . . ?
C3 C2 C15 C16 4.9(4) . . . . ?
C20 C15 C16 C17 -0.3(4) . . . . ?
C2 C15 C16 C17 179.1(3) . . . . ?
C15 C16 C17 C18 -0.4(5) . . . . ?
C16 C17 C18 C19 0.6(5) . . . . ?
C16 C17 C18 O1 180.0(3) . . . . ?
C17 C18 C19 C20 -0.2(4) . . . . ?
O1 C18 C19 C20 -179.5(3) . . . . ?
C16 C15 C20 C19 0.7(4) . . . . ?
C2 C15 C20 C19 -178.7(3) . . . . ?
C18 C19 C20 C15 -0.5(4) . . . . ?
N2 C10 N1 C2 -0.2(3) . . . . ?
C9 C10 N1 C2 -178.9(3) . . . . ?
C3 C2 N1 C10 -0.9(3) . . . . ?
C15 C2 N1 C10 178.1(2) . . . . ?
N1 C10 N2 C3 1.3(3) . . . . ?
C9 C10 N2 C3 -179.6(2) . . . . ?
N1 C10 N2 C6 -176.4(2) . . . . ?
C9 C10 N2 C6 2.7(4) . . . . ?
C2 C3 N2 C10 -1.7(3) . . . . ?
C4 C3 N2 C10 179.1(2) . . . . ?
C2 C3 N2 C6 176.2(2) . . . . ?
C4 C3 N2 C6 -2.9(3) . . . . ?
C7 C6 N2 C10 -2.8(4) . . . . ?
C5 C6 N2 C10 179.5(2) . . . . ?
C7 C6 N2 C3 179.7(2) . . . . ?
C5 C6 N2 C3 1.9(3) . . . . ?
C19 C18 O1 C21 -4.4(4) . . . . ?
C17 C18 O1 C21 176.2(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659190
2 PubChem 46217510
