#------------------------------------------------------------------------------
#$Date: 2026-03-07 02:10:42 +0100 (Sat 07 de Mar de 2026) $
#$Revision: 304988 $
#$URL: svn://www.crystallography.net/cod/cif/7/72/05/7720589.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_7720589
loop_
_publ_author_name
'Pariyacheri Padikkal, Hrudya'
'Jeannin, Olivier'
'Rouzières, Mathieu'
'Clérac, Rodolphe'
'Jeon, Ie-Rang'
'Fourmigué, Marc'
_publ_section_title
;
 Chalcogen bond activation in cation radical salts of naphthalene
 peri-diselenides with S = 5/2 magnetic anions
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D6DT00277C
_journal_year                    2026
_chemical_formula_moiety         'C12 H10 O2 Se2, Br4 Fe'
_chemical_formula_sum            'C12 H10 Br4 Fe O2 Se2'
_chemical_formula_weight         719.61
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2025-01-22T14:13:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2025-10-23 deposited with the CCDC.	2026-03-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.701(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.9157(5)
_cell_length_b                   24.6933(19)
_cell_length_c                   10.9028(7)
_cell_measurement_reflns_used    9888
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.13
_cell_measurement_wavelength     0.71073
_cell_volume                     1816.3(2)
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean 7.39
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_orient_matrix_UB_11      -0.060744
_diffrn_orient_matrix_UB_12      -0.03694
_diffrn_orient_matrix_UB_13      -0.00829
_diffrn_orient_matrix_UB_21      -0.134954
_diffrn_orient_matrix_UB_22      0.016559
_diffrn_orient_matrix_UB_23      -0.024514
_diffrn_orient_matrix_UB_31      0.008275
_diffrn_orient_matrix_UB_32      -0.001103
_diffrn_orient_matrix_UB_33      -0.090388
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            20229
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         3.129
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    13.636
_exptl_absorpt_correction_T_max  0.761
_exptl_absorpt_correction_T_min  0.446
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    2.632
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.686
_refine_diff_density_min         -1.033
_refine_diff_density_rms         0.145
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     192
_refine_ls_number_reflns         4144
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0307
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0207P)²+5.3018P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0661
_refine_ls_wR_factor_ref         0.0682
_reflns_Friedel_coverage         0
_reflns_number_gt                3613
_reflns_number_total             4144
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d6dt00277c2.cif
_cod_data_source_block           shelx_CCDC4
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7720589
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2474(5) 0.45412(17) 0.4996(3) 0.0178(8) Uani 1 1 d . . . . .
C2 C 0.2122(5) 0.40675(17) 0.4264(4) 0.0190(8) Uani 1 1 d . . . . .
C3 C 0.1234(5) 0.41076(17) 0.2983(4) 0.0214(8) Uani 1 1 d . . . . .
H3 H 0.103312 0.378942 0.248132 0.026 Uiso 1 1 calc R U . . .
C4 C 0.0641(6) 0.46069(18) 0.2433(4) 0.0226(8) Uani 1 1 d . . . . .
H4 H -0.003894 0.462393 0.157627 0.027 Uiso 1 1 calc R U . . .
C5 C 0.1047(5) 0.50909(17) 0.3148(4) 0.0193(8) Uani 1 1 d . . . . .
C6 C 0.1972(5) 0.50507(16) 0.4455(3) 0.0148(7) Uani 1 1 d . . . . .
C7 C 0.2373(5) 0.55213(16) 0.5187(3) 0.0162(7) Uani 1 1 d . . . . .
C8 C 0.1900(5) 0.60342(17) 0.4651(4) 0.0197(8) Uani 1 1 d . . . . .
C9 C 0.0978(5) 0.60719(18) 0.3375(4) 0.0218(8) Uani 1 1 d . . . . .
H9 H 0.067217 0.641846 0.300423 0.026 Uiso 1 1 calc R U . . .
C10 C 0.0502(6) 0.56091(17) 0.2640(4) 0.0226(8) Uani 1 1 d . . . . .
H10 H -0.019552 0.56423 0.178923 0.027 Uiso 1 1 calc R U . . .
C11 C 0.2552(7) 0.31117(18) 0.4160(5) 0.0318(10) Uani 1 1 d . . . . .
H11A H 0.116112 0.305163 0.374602 0.048 Uiso 1 1 calc R U . . .
H11B H 0.302959 0.280685 0.472102 0.048 Uiso 1 1 calc R U . . .
H11C H 0.33504 0.314084 0.352362 0.048 Uiso 1 1 calc R U . . .
C12 C 0.2087(7) 0.69945(18) 0.4906(5) 0.0319(10) Uani 1 1 d . . . . .
H12A H 0.289256 0.704488 0.427862 0.048 Uiso 1 1 calc R U . . .
H12B H 0.24723 0.726256 0.557788 0.048 Uiso 1 1 calc R U . . .
H12C H 0.068336 0.704129 0.450501 0.048 Uiso 1 1 calc R U . . .
Br1 Br 1.01298(6) 0.33162(2) 0.98439(4) 0.03079(11) Uani 1 1 d . . . . .
Br2 Br 0.47846(7) 0.31444(2) 0.79188(4) 0.03029(11) Uani 1 1 d . . . . .
Br3 Br 0.59479(8) 0.31708(2) 1.15394(4) 0.03852(13) Uani 1 1 d . . . . .
Br4 Br 0.64083(6) 0.44539(2) 0.96851(4) 0.02908(11) Uani 1 1 d . . . . .
Fe1 Fe 0.67904(8) 0.35085(2) 0.97349(5) 0.02161(13) Uani 1 1 d . . . . .
O1 O 0.2722(4) 0.36062(12) 0.4883(3) 0.0260(6) Uani 1 1 d . . . . .
O2 O 0.2404(4) 0.64539(12) 0.5432(3) 0.0249(6) Uani 1 1 d . . . . .
Se1 Se 0.37329(5) 0.45072(2) 0.66967(3) 0.01866(9) Uani 1 1 d . . . . .
Se2 Se 0.36155(5) 0.54425(2) 0.68864(3) 0.01857(9) 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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 '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
C6 C1 C2 120.8(3) . . ?
C6 C1 Se1 118.5(3) . . ?
C2 C1 Se1 120.7(3) . . ?
O1 C2 C3 125.5(4) . . ?
O1 C2 C1 115.1(3) . . ?
C3 C2 C1 119.4(4) . . ?
C4 C3 C2 121.0(4) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 120.3(4) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C10 C5 C4 122.9(4) . . ?
C10 C5 C6 118.4(4) . . ?
C4 C5 C6 118.6(4) . . ?
C1 C6 C7 120.3(3) . . ?
C1 C6 C5 119.8(4) . . ?
C7 C6 C5 119.9(4) . . ?
C6 C7 C8 120.8(3) . . ?
C6 C7 Se2 117.9(3) . . ?
C8 C7 Se2 121.3(3) . . ?
O2 C8 C9 125.3(4) . . ?
O2 C8 C7 115.5(3) . . ?
C9 C8 C7 119.1(4) . . ?
C10 C9 C8 121.0(4) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C5 120.6(4) . . ?
C9 C10 H10 119.7 . . ?
C5 C10 H10 119.7 . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
Br3 Fe1 Br2 111.52(3) . . ?
Br3 Fe1 Br1 108.23(3) . . ?
Br2 Fe1 Br1 111.19(3) . . ?
Br3 Fe1 Br4 109.16(3) . . ?
Br2 Fe1 Br4 108.69(3) . . ?
Br1 Fe1 Br4 107.96(3) . . ?
C2 O1 C11 117.6(3) . . ?
C8 O2 C12 117.8(3) . . ?
C1 Se1 Se2 91.48(13) . . ?
C7 Se2 Se1 91.87(12) . . ?
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
C1 C6 1.401(5) . ?
C1 C2 1.407(6) . ?
C1 Se1 1.869(4) . ?
C2 O1 1.343(5) . ?
C2 C3 1.400(5) . ?
C3 C4 1.393(6) . ?
C3 H3 0.95 . ?
C4 C5 1.421(6) . ?
C4 H4 0.95 . ?
C5 C10 1.412(6) . ?
C5 C6 1.431(5) . ?
C6 C7 1.402(5) . ?
C7 C8 1.403(6) . ?
C7 Se2 1.874(4) . ?
C8 O2 1.338(5) . ?
C8 C9 1.401(5) . ?
C9 C10 1.393(6) . ?
C9 H9 0.95 . ?
C10 H10 0.95 . ?
C11 O1 1.444(5) . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C12 O2 1.450(5) . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
Br1 Fe1 2.3351(7) . ?
Br2 Fe1 2.3336(7) . ?
Br3 Fe1 2.3259(7) . ?
Br4 Fe1 2.3487(8) . ?
Se1 Se2 2.3219(6) . ?
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
C6 C1 C2 O1 178.1(3) . . . . ?
Se1 C1 C2 O1 1.1(4) . . . . ?
C6 C1 C2 C3 -0.9(5) . . . . ?
Se1 C1 C2 C3 -177.9(3) . . . . ?
O1 C2 C3 C4 179.2(4) . . . . ?
C1 C2 C3 C4 -2.0(5) . . . . ?
C2 C3 C4 C5 4.2(6) . . . . ?
C3 C4 C5 C10 179.3(4) . . . . ?
C3 C4 C5 C6 -3.5(5) . . . . ?
C2 C1 C6 C7 -178.4(3) . . . . ?
Se1 C1 C6 C7 -1.3(4) . . . . ?
C2 C1 C6 C5 1.5(5) . . . . ?
Se1 C1 C6 C5 178.6(2) . . . . ?
C10 C5 C6 C1 178.0(3) . . . . ?
C4 C5 C6 C1 0.7(5) . . . . ?
C10 C5 C6 C7 -2.1(5) . . . . ?
C4 C5 C6 C7 -179.4(3) . . . . ?
C1 C6 C7 C8 179.2(3) . . . . ?
C5 C6 C7 C8 -0.8(5) . . . . ?
C1 C6 C7 Se2 0.7(4) . . . . ?
C5 C6 C7 Se2 -179.2(2) . . . . ?
C6 C7 C8 O2 -178.1(3) . . . . ?
Se2 C7 C8 O2 0.3(5) . . . . ?
C6 C7 C8 C9 1.4(5) . . . . ?
Se2 C7 C8 C9 179.7(3) . . . . ?
O2 C8 C9 C10 -179.7(3) . . . . ?
C7 C8 C9 C10 0.9(6) . . . . ?
C8 C9 C10 C5 -3.8(6) . . . . ?
C4 C5 C10 C9 -178.5(4) . . . . ?
C6 C5 C10 C9 4.3(5) . . . . ?
C3 C2 O1 C11 4.0(5) . . . . ?
C1 C2 O1 C11 -175.0(3) . . . . ?
C9 C8 O2 C12 -4.0(5) . . . . ?
C7 C8 O2 C12 175.4(3) . . . . ?
C6 C1 Se1 Se2 1.1(3) . . . . ?
C2 C1 Se1 Se2 178.2(3) . . . . ?
C6 C7 Se2 Se1 0.1(3) . . . . ?
C8 C7 Se2 Se1 -178.4(3) . . . . ?
