#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/74/7157479.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_7157479
loop_
_publ_author_name
'Recchi, Ana Maria S.'
'Rosa, Pedro H. P.'
'Back, Davi F.'
'Zeni, Gilson'
_publ_section_title
;
 Selenium-promoted electrophilic cyclization of arylpropiolamides:
 synthesis of 3-organoselenyl spiro[4,5]trienones.
;
_journal_issue                   18
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3544
_journal_page_last               3551
_journal_paper_doi               10.1039/d0ob00609b
_journal_volume                  18
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C22 H17 N O2 Se'
_chemical_formula_sum            'C22 H17 N O2 Se'
_chemical_formula_weight         406.32
_chemical_melting_point          ?
_chemical_name_common            'azaspiro deca trienedione'
_chemical_name_systematic
;
1-methyl-4-phenyl-3-(phenylselanyl)-1-azaspiro[4.5]deca-3,7,9-triene-2,6-dione
;
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_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      2.4
_audit_creation_date             2019-06-14T17:16:50-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2020-03-19 deposited with the CCDC.	2020-04-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.129(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6477(5)
_cell_length_b                   14.9116(8)
_cell_length_c                   13.3181(7)
_cell_measurement_reflns_used    9259
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.547
_cell_measurement_theta_min      2.532
_cell_volume                     1896.73(17)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Diamond (version 3.2i); Crystal Impact GbR'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL-2008 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       '2° φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            78808
_diffrn_reflns_theta_full        28.4
_diffrn_reflns_theta_max         28.4
_diffrn_reflns_theta_min         2.53
_diffrn_source                   'micro-focus tube'
_exptl_absorpt_coefficient_mu    1.995
_exptl_absorpt_correction_T_max  0.6811
_exptl_absorpt_correction_T_min  0.5201
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
        absorption correction based on the indexed faces of the crystal.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.54
_refine_diff_density_min         -0.562
_refine_diff_density_rms         0.18
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.021(7)
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         9479
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0377
_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)+(0.0699P)²+0.0316P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1104
_reflns_number_gt                7599
_reflns_number_total             9479
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            d0ob00609b2.cif
_cod_data_source_block           teste2_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value 'none' was changed to '?'
-- the value is undefined or not given.

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7157478--7157479.cif.

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_Hall     P-2yc
_cod_original_sg_symbol_H-M      P1c1
_cod_original_formula_moiety     'C44 H34 N2 O4 Se2'
_cod_original_formula_sum        'C44 H34 N2 O4 Se2'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     812.65
_cod_database_code               7157479
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, 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
Se37 Se 0.60344(3) 0.25062(2) 0.29067(3) 0.06019(10) Uani 1 1 d . . .
Se11 Se 0.09038(4) 0.26893(3) 0.76587(3) 0.08211(16) Uani 1 1 d . . .
O39 O 0.5804(2) 0.46518(16) 0.36095(17) 0.0632(5) Uani 1 1 d . . .
O52 O 0.9089(3) 0.4933(2) 0.1839(2) 0.0899(8) Uani 1 1 d . . .
O26 O 0.4130(3) 0.0008(2) 0.7514(2) 0.0855(8) Uani 1 1 d . . .
N33 N 0.8184(2) 0.48140(17) 0.37314(19) 0.0553(6) Uani 1 1 d . . .
O13 O 0.1208(3) 0.1010(2) 0.9348(2) 0.0975(10) Uani 1 1 d . . .
C4 C 0.5010(3) 0.0513(2) 0.7919(2) 0.0609(8) Uani 1 1 d . . .
C10 C 0.3664(3) 0.1929(2) 0.79757(18) 0.0483(6) Uani 1 1 d . . .
C42 C 0.5411(3) 0.3667(2) 0.1155(2) 0.0581(7) Uani 1 1 d . . .
H42 H 0.6305 0.3904 0.1329 0.07 Uiso 1 1 calc R . .
C35 C 0.7345(3) 0.34521(19) 0.3205(2) 0.0474(6) Uani 1 1 d . . .
N7 N 0.3555(3) 0.0891(2) 0.92431(18) 0.0675(7) Uani 1 1 d . . .
C34 C 0.6976(3) 0.4356(2) 0.35230(19) 0.0495(6) Uani 1 1 d . . .
C31 C 0.9377(3) 0.4299(2) 0.3512(2) 0.0530(6) Uani 1 1 d . . .
C41 C 0.4927(3) 0.3014(2) 0.1741(2) 0.0496(6) Uani 1 1 d . . .
C5 C 0.4562(3) 0.1244(2) 0.86366(19) 0.0526(6) Uani 1 1 d . . .
C9 C 0.2364(3) 0.1897(2) 0.8187(2) 0.0576(7) Uani 1 1 d . . .
C15 C -0.0141(3) 0.1947(2) 0.6661(2) 0.0590(7) Uani 1 1 d . . .
C36 C 0.8718(3) 0.33850(19) 0.3214(2) 0.0485(6) Uani 1 1 d . . .
C6 C 0.5769(4) 0.1713(3) 0.9277(2) 0.0738(10) Uani 1 1 d . . .
H6 H 0.5594 0.2089 0.9802 0.089 Uiso 1 1 calc R . .
C32 C 1.0466(3) 0.4217(3) 0.4439(3) 0.0731(9) Uani 1 1 d . . .
H32 H 1.0181 0.4128 0.507 0.088 Uiso 1 1 calc R . .
C3 C 0.6457(4) 0.0477(4) 0.7779(3) 0.0867(12) Uani 1 1 d . . .
H3 H 0.6735 0.0095 0.7292 0.104 Uiso 1 1 calc R . .
C16 C 0.0326(4) 0.1145(3) 0.6341(3) 0.0744(9) Uani 1 1 d . . .
H16 H 0.1192 0.0924 0.6631 0.089 Uiso 1 1 calc R . .
C30 C 0.9920(4) 0.4655(3) 0.2551(3) 0.0655(8) Uani 1 1 d . . .
C43 C 0.4541(4) 0.3973(2) 0.0294(2) 0.0723(9) Uani 1 1 d . . .
H43 H 0.4861 0.4414 -0.0111 0.087 Uiso 1 1 calc R . .
C12 C 0.4208(4) 0.2478(2) 0.7196(2) 0.0525(7) Uani 1 1 d . . .
C21 C 0.4978(4) 0.3238(2) 0.7445(3) 0.0680(8) Uani 1 1 d . . .
H21 H 0.5193 0.341 0.812 0.082 Uiso 1 1 calc R . .
C17 C -0.0480(5) 0.0664(3) 0.5590(3) 0.0894(12) Uani 1 1 d . . .
H17 H -0.0152 0.0126 0.5361 0.107 Uiso 1 1 calc R . .
C40 C 0.8298(4) 0.5737(2) 0.4060(3) 0.0724(9) Uani 1 1 d . . .
H40A H 0.9264 0.5914 0.4153 0.109 Uiso 1 1 calc R . .
H40B H 0.793 0.5798 0.4689 0.109 Uiso 1 1 calc R . .
H40C H 0.7776 0.6111 0.3555 0.109 Uiso 1 1 calc R . .
C22 C 0.5437(5) 0.3752(3) 0.6687(4) 0.0866(11) Uani 1 1 d . . .
H22 H 0.5947 0.4273 0.6854 0.104 Uiso 1 1 calc R . .
C8 C 0.2247(4) 0.1217(3) 0.8981(2) 0.0687(9) Uani 1 1 d . . .
C1 C 0.7068(4) 0.1595(3) 0.9099(4) 0.0948(15) Uani 1 1 d . . .
H1 H 0.7782 0.1918 0.9478 0.114 Uiso 1 1 calc R . .
C38 C 0.9538(3) 0.2614(2) 0.2915(3) 0.0568(7) Uani 1 1 d . . .
C27 C 1.1783(4) 0.4269(3) 0.4373(4) 0.0926(14) Uani 1 1 d . . .
H27 H 1.2424 0.42 0.4959 0.111 Uiso 1 1 calc R . .
C23 C 0.5139(5) 0.3492(3) 0.5694(3) 0.0880(13) Uani 1 1 d . . .
H23 H 0.5476 0.3825 0.519 0.106 Uiso 1 1 calc R . .
C46 C 0.3580(4) 0.2675(3) 0.1489(3) 0.0679(9) Uani 1 1 d . . .
H46 H 0.3237 0.2247 0.1899 0.081 Uiso 1 1 calc R . .
C2 C 0.7416(4) 0.0989(4) 0.8346(4) 0.0959(14) Uani 1 1 d . . .
H2 H 0.8346 0.0945 0.8241 0.115 Uiso 1 1 calc R . .
C20 C -0.1427(5) 0.2276(3) 0.6240(3) 0.0813(11) Uani 1 1 d . . .
H20 H -0.1752 0.282 0.6457 0.098 Uiso 1 1 calc R . .
C44 C 0.3237(5) 0.3631(3) 0.0045(3) 0.0775(11) Uani 1 1 d . . .
H44 H 0.2665 0.3842 -0.0528 0.093 Uiso 1 1 calc R . .
C18 C -0.1775(5) 0.0986(4) 0.5182(4) 0.0981(14) Uani 1 1 d . . .
H18 H -0.234 0.0655 0.4693 0.118 Uiso 1 1 calc R . .
C45 C 0.2756(4) 0.2982(3) 0.0625(3) 0.0809(11) Uani 1 1 d . . .
H45 H 0.1866 0.2743 0.0439 0.097 Uiso 1 1 calc R . .
C29 C 1.1433(4) 0.4595(3) 0.2557(5) 0.0925(14) Uani 1 1 d . . .
H29 H 1.1814 0.4673 0.196 0.111 Uiso 1 1 calc R . .
C28 C 1.2286(4) 0.4424(3) 0.3448(6) 0.1080(19) Uani 1 1 d . . .
H28 H 1.3248 0.4411 0.3441 0.13 Uiso 1 1 calc R . .
C19 C -0.2224(5) 0.1785(4) 0.5491(3) 0.1015(16) Uani 1 1 d . . .
H19 H -0.3087 0.2007 0.5195 0.122 Uiso 1 1 calc R . .
C25 C 0.3881(4) 0.2227(3) 0.6186(3) 0.0686(8) Uani 1 1 d . . .
H25 H 0.3352 0.1715 0.6012 0.082 Uiso 1 1 calc R . .
C14 C 0.3915(5) 0.0199(4) 0.9995(3) 0.1053(16) Uani 1 1 d . . .
H14A H 0.49 0.0076 1.0056 0.158 Uiso 1 1 calc R . .
H14B H 0.3397 -0.0336 0.9792 0.158 Uiso 1 1 calc R . .
H14C H 0.3687 0.0399 1.0637 0.158 Uiso 1 1 calc R . .
C47 C 0.9378(5) 0.2370(3) 0.1908(4) 0.0785(11) Uani 1 1 d . . .
H47 H 0.8781 0.2696 0.1433 0.094 Uiso 1 1 calc R . .
C49 C 1.0989(5) 0.1167(3) 0.2319(6) 0.114(2) Uani 1 1 d . . .
H49 H 1.1476 0.0672 0.2126 0.136 Uiso 1 1 calc R . .
C51 C 1.0427(4) 0.2143(3) 0.3603(4) 0.0823(11) Uani 1 1 d . . .
H51 H 1.0553 0.2309 0.4283 0.099 Uiso 1 1 calc R . .
C48 C 1.0104(5) 0.1643(4) 0.1603(5) 0.1062(16) Uani 1 1 d . . .
H48 H 0.9998 0.1476 0.0923 0.127 Uiso 1 1 calc R . .
C24 C 0.4353(5) 0.2749(3) 0.5441(3) 0.0810(11) Uani 1 1 d . . .
H24 H 0.4129 0.2588 0.4763 0.097 Uiso 1 1 calc R . .
C50 C 1.1138(5) 0.1422(3) 0.3289(5) 0.1056(16) Uani 1 1 d . . .
H50 H 1.1741 0.1102 0.3766 0.127 Uiso 1 1 calc R . .
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'
Se Se -0.0929 2.2259 '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
C35 Se37 C41 98.91(12) . . ?
C9 Se11 C15 100.90(13) . . ?
C34 N33 C40 124.9(3) . . ?
C34 N33 C31 112.3(2) . . ?
C40 N33 C31 122.6(2) . . ?
O26 C4 C3 123.7(4) . . ?
O26 C4 C5 118.4(3) . . ?
C3 C4 C5 117.9(3) . . ?
C9 C10 C12 127.7(3) . . ?
C9 C10 C5 109.2(3) . . ?
C12 C10 C5 123.0(2) . . ?
C41 C42 C43 119.0(3) . . ?
C36 C35 C34 110.4(2) . . ?
C36 C35 Se37 125.5(2) . . ?
C34 C35 Se37 124.07(19) . . ?
C8 N7 C14 124.0(3) . . ?
C8 N7 C5 113.7(3) . . ?
C14 N7 C5 122.1(3) . . ?
O39 C34 N33 125.3(3) . . ?
O39 C34 C35 128.0(3) . . ?
N33 C34 C35 106.7(2) . . ?
N33 C31 C32 111.1(3) . . ?
N33 C31 C36 102.3(2) . . ?
C32 C31 C36 110.8(3) . . ?
N33 C31 C30 110.9(3) . . ?
C32 C31 C30 115.3(3) . . ?
C36 C31 C30 105.5(2) . . ?
C42 C41 C46 120.2(3) . . ?
C42 C41 Se37 123.2(2) . . ?
C46 C41 Se37 116.6(2) . . ?
N7 C5 C6 112.2(2) . . ?
N7 C5 C10 101.2(2) . . ?
C6 C5 C10 110.0(3) . . ?
N7 C5 C4 110.8(3) . . ?
C6 C5 C4 114.4(3) . . ?
C10 C5 C4 107.4(2) . . ?
C10 C9 C8 110.3(3) . . ?
C10 C9 Se11 125.1(2) . . ?
C8 C9 Se11 124.3(2) . . ?
C16 C15 C20 120.1(4) . . ?
C16 C15 Se11 124.1(2) . . ?
C20 C15 Se11 115.7(3) . . ?
C35 C36 C38 128.8(3) . . ?
C35 C36 C31 108.2(2) . . ?
C38 C36 C31 122.8(2) . . ?
C1 C6 C5 120.7(4) . . ?
C27 C32 C31 121.3(4) . . ?
C2 C3 C4 120.7(5) . . ?
C15 C16 C17 120.3(3) . . ?
O52 C30 C29 124.7(4) . . ?
O52 C30 C31 119.8(3) . . ?
C29 C30 C31 115.4(4) . . ?
C44 C43 C42 120.5(3) . . ?
C21 C12 C25 119.9(3) . . ?
C21 C12 C10 121.5(3) . . ?
C25 C12 C10 118.5(3) . . ?
C12 C21 C22 119.9(4) . . ?
C18 C17 C16 119.5(4) . . ?
C23 C22 C21 120.1(4) . . ?
O13 C8 N7 126.8(4) . . ?
O13 C8 C9 127.7(4) . . ?
N7 C8 C9 105.5(3) . . ?
C6 C1 C2 122.4(4) . . ?
C51 C38 C47 119.5(3) . . ?
C51 C38 C36 122.0(4) . . ?
C47 C38 C36 118.4(3) . . ?
C32 C27 C28 122.4(4) . . ?
C24 C23 C22 120.3(3) . . ?
C45 C46 C41 119.3(3) . . ?
C3 C2 C1 122.9(4) . . ?
C15 C20 C19 118.9(4) . . ?
C43 C44 C45 120.5(3) . . ?
C19 C18 C17 119.9(4) . . ?
C44 C45 C46 120.4(3) . . ?
C28 C29 C30 119.6(4) . . ?
C29 C28 C27 123.4(3) . . ?
C18 C19 C20 121.2(4) . . ?
C12 C25 C24 119.3(4) . . ?
C38 C47 C48 120.1(5) . . ?
C50 C49 C48 119.5(4) . . ?
C38 C51 C50 119.7(5) . . ?
C47 C48 C49 119.3(5) . . ?
C23 C24 C25 120.6(4) . . ?
C49 C50 C51 121.9(5) . . ?
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
Se37 C35 1.898(3) . ?
Se37 C41 1.912(3) . ?
Se11 C9 1.896(3) . ?
Se11 C15 1.905(3) . ?
O39 C34 1.234(3) . ?
O52 C30 1.224(5) . ?
O26 C4 1.204(4) . ?
N33 C34 1.346(4) . ?
N33 C40 1.443(4) . ?
N33 C31 1.447(4) . ?
O13 C8 1.215(4) . ?
C4 C3 1.435(5) . ?
C4 C5 1.551(5) . ?
C10 C9 1.325(4) . ?
C10 C12 1.476(4) . ?
C10 C5 1.534(4) . ?
C42 C41 1.371(4) . ?
C42 C43 1.399(5) . ?
C35 C36 1.327(4) . ?
C35 C34 1.472(4) . ?
N7 C8 1.351(5) . ?
N7 C14 1.445(5) . ?
N7 C5 1.448(4) . ?
C31 C32 1.509(4) . ?
C31 C36 1.532(4) . ?
C31 C30 1.545(5) . ?
C41 C46 1.390(4) . ?
C5 C6 1.514(4) . ?
C9 C8 1.482(5) . ?
C15 C16 1.367(5) . ?
C15 C20 1.377(5) . ?
C36 C38 1.481(4) . ?
C6 C1 1.320(6) . ?
C32 C27 1.288(5) . ?
C3 C2 1.346(7) . ?
C16 C17 1.378(6) . ?
C30 C29 1.461(5) . ?
C43 C44 1.355(6) . ?
C12 C21 1.370(5) . ?
C12 C25 1.388(5) . ?
C21 C22 1.389(5) . ?
C17 C18 1.377(6) . ?
C22 C23 1.369(7) . ?
C1 C2 1.425(8) . ?
C38 C51 1.358(5) . ?
C38 C47 1.377(6) . ?
C27 C28 1.406(8) . ?
C23 C24 1.358(7) . ?
C46 C45 1.381(6) . ?
C20 C19 1.381(7) . ?
C44 C45 1.361(6) . ?
C18 C19 1.351(7) . ?
C29 C28 1.369(9) . ?
C25 C24 1.387(6) . ?
C47 C48 1.383(6) . ?
C49 C50 1.336(9) . ?
C49 C48 1.383(9) . ?
C51 C50 1.373(6) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168353388
