# Supplementary Information (SI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2497447'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University Rennes
France
;
_audit_update_record             
;
2025-10-23 deposited with the CCDC.	2026-03-05 downloaded from the CCDC.
;

_audit_creation_date             2023-04-26T17:26:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C12 H10 O2 Se2, Cl4 Fe'
_chemical_formula_sum            'C12 H10 Cl4 Fe O2 Se2'
_chemical_formula_weight         541.77

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
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'

_cell_length_a                   6.8876(6)
_cell_length_b                   24.250(2)
_cell_length_c                   10.5956(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.284(3)
_cell_angle_gamma                90
_cell_volume                     1729.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9899
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      27.51
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    2.081
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1040

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    5.698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.718
_exptl_absorpt_correction_T_max  0.843

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.5855  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
# Ratio of Min/Max transmission:               0.7853                          #
#------------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean 7.39
_diffrn_orient_matrix_ub_11      0.114031
_diffrn_orient_matrix_ub_12      -0.01357
_diffrn_orient_matrix_ub_13      0.067703
_diffrn_orient_matrix_ub_21      0.040127
_diffrn_orient_matrix_ub_22      -0.025258
_diffrn_orient_matrix_ub_23      -0.064566
_diffrn_orient_matrix_ub_31      0.086407
_diffrn_orient_matrix_ub_32      0.029638
_diffrn_orient_matrix_ub_33      -0.024025
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_number            23280
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.587
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_coverage         0
_reflns_number_total             3961
_reflns_number_gt                3487
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0071P)²+2.0156P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3961
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0242
_refine_ls_wR_factor_ref         0.0479
_refine_ls_wR_factor_gt          0.0463
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.076

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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'
Cl Cl 0.1484 0.1585 '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'
Se Se -0.0929 2.2259 '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_
_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 0.7531(3) 0.54671(9) 0.5010(2) 0.0156(4) Uani 1 1 d . . . . .
C2 C 0.7886(3) 0.59499(9) 0.5749(2) 0.0185(5) Uani 1 1 d . . . . .
C3 C 0.8767(4) 0.59131(10) 0.7062(2) 0.0207(5) Uani 1 1 d . . . . .
H3 H 0.899437 0.623796 0.757288 0.025 Uiso 1 1 calc R U . . .
C4 C 0.9311(4) 0.54041(10) 0.7620(2) 0.0202(5) Uani 1 1 d . . . . .
H4 H 0.994904 0.538781 0.850743 0.024 Uiso 1 1 calc R U . . .
C5 C 0.8944(3) 0.49097(9) 0.6909(2) 0.0169(5) Uani 1 1 d . . . . .
C6 C 0.8027(3) 0.49474(9) 0.5570(2) 0.0151(4) Uani 1 1 d . . . . .
C7 C 0.7615(3) 0.44669(9) 0.4825(2) 0.0154(4) Uani 1 1 d . . . . .
C8 C 0.8078(3) 0.39447(10) 0.5385(2) 0.0179(5) Uani 1 1 d . . . . .
C9 C 0.8991(4) 0.39082(10) 0.6689(2) 0.0209(5) Uani 1 1 d . . . . .
H9 H 0.930342 0.355666 0.707458 0.025 Uiso 1 1 calc R U . . .
C10 C 0.9444(4) 0.43803(10) 0.7426(2) 0.0195(5) Uani 1 1 d . . . . .
H10 H 1.011005 0.434665 0.83052 0.023 Uiso 1 1 calc R U . . .
C11 C 0.7471(4) 0.69254(10) 0.5825(3) 0.0325(6) Uani 1 1 d . . . . .
H11A H 0.665482 0.690346 0.647681 0.049 Uiso 1 1 calc R U . . .
H11B H 0.7012 0.723308 0.523755 0.049 Uiso 1 1 calc R U . . .
H11C H 0.886259 0.698472 0.625276 0.049 Uiso 1 1 calc R U . . .
C12 C 0.7837(5) 0.29655(10) 0.5130(3) 0.0318(6) Uani 1 1 d . . . . .
H12A H 0.922985 0.291564 0.556721 0.048 Uiso 1 1 calc R U . . .
H12B H 0.748118 0.269164 0.443947 0.048 Uiso 1 1 calc R U . . .
H12C H 0.698469 0.291769 0.575433 0.048 Uiso 1 1 calc R U . . .
Cl1 Cl 0.52178(11) 0.68253(3) 0.19843(6) 0.03240(16) Uani 1 1 d . . . . .
Cl2 Cl 0.02277(10) 0.66724(3) 0.01112(6) 0.03151(15) Uani 1 1 d . . . . .
Cl3 Cl 0.42450(13) 0.67942(3) -0.15025(7) 0.04263(19) Uani 1 1 d . . . . .
Cl4 Cl 0.36906(10) 0.55674(2) 0.02769(6) 0.02807(14) Uani 1 1 d . . . . .
Fe1 Fe 0.33769(6) 0.64742(2) 0.02252(3) 0.02242(9) Uani 1 1 d . . . . .
Se1 Se 0.62816(3) 0.54962(2) 0.32586(2) 0.01752(6) Uani 1 1 d . . . . .
Se2 Se 0.63853(3) 0.45428(2) 0.30793(2) 0.01728(6) Uani 1 1 d . . . . .
O1 O 0.7298(3) 0.64184(7) 0.51025(16) 0.0247(4) Uani 1 1 d . . . . .
O2 O 0.7564(3) 0.35143(7) 0.45832(16) 0.0236(4) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C2 1.400(3) . ?
C1 C6 1.404(3) . ?
C1 Se1 1.874(2) . ?
C2 O1 1.344(3) . ?
C2 C3 1.397(3) . ?
C3 C4 1.385(3) . ?
C3 H3 0.95 . ?
C4 C5 1.410(3) . ?
C4 H4 0.95 . ?
C5 C10 1.409(3) . ?
C5 C6 1.428(3) . ?
C6 C7 1.402(3) . ?
C7 C8 1.406(3) . ?
C7 Se2 1.872(2) . ?
C8 O2 1.345(3) . ?
C8 C9 1.394(3) . ?
C9 C10 1.384(3) . ?
C9 H9 0.95 . ?
C10 H10 0.95 . ?
C11 O1 1.440(3) . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C12 O2 1.448(3) . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
Cl1 Fe1 2.1912(7) . ?
Cl2 Fe1 2.1997(8) . ?
Cl3 Fe1 2.1855(8) . ?
Cl4 Fe1 2.2090(7) . ?
Se1 Se2 2.3222(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
C2 C1 C6 121.1(2) . . ?
C2 C1 Se1 120.73(17) . . ?
C6 C1 Se1 118.15(16) . . ?
O1 C2 C3 125.6(2) . . ?
O1 C2 C1 115.1(2) . . ?
C3 C2 C1 119.4(2) . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 121.9(2) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C10 C5 C4 124.5(2) . . ?
C10 C5 C6 117.7(2) . . ?
C4 C5 C6 117.9(2) . . ?
C7 C6 C1 120.4(2) . . ?
C7 C6 C5 120.0(2) . . ?
C1 C6 C5 119.6(2) . . ?
C6 C7 C8 120.7(2) . . ?
C6 C7 Se2 118.01(16) . . ?
C8 C7 Se2 121.32(17) . . ?
O2 C8 C9 125.4(2) . . ?
O2 C8 C7 115.3(2) . . ?
C9 C8 C7 119.3(2) . . ?
C10 C9 C8 120.5(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C5 121.8(2) . . ?
C9 C10 H10 119.1 . . ?
C5 C10 H10 119.1 . . ?
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 . . ?
Cl3 Fe1 Cl1 111.26(3) . . ?
Cl3 Fe1 Cl2 108.59(3) . . ?
Cl1 Fe1 Cl2 110.31(3) . . ?
Cl3 Fe1 Cl4 109.36(3) . . ?
Cl1 Fe1 Cl4 109.26(3) . . ?
Cl2 Fe1 Cl4 108.00(3) . . ?
C1 Se1 Se2 91.60(7) . . ?
C7 Se2 Se1 91.86(7) . . ?
C2 O1 C11 117.97(19) . . ?
C8 O2 C12 117.80(19) . . ?

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 -178.4(2) . . . . ?
Se1 C1 C2 O1 -0.9(3) . . . . ?
C6 C1 C2 C3 0.6(3) . . . . ?
Se1 C1 C2 C3 178.12(17) . . . . ?
O1 C2 C3 C4 180.0(2) . . . . ?
C1 C2 C3 C4 1.0(4) . . . . ?
C2 C3 C4 C5 -2.1(4) . . . . ?
C3 C4 C5 C10 -179.3(2) . . . . ?
C3 C4 C5 C6 1.5(3) . . . . ?
C2 C1 C6 C7 178.4(2) . . . . ?
Se1 C1 C6 C7 0.8(3) . . . . ?
C2 C1 C6 C5 -1.2(3) . . . . ?
Se1 C1 C6 C5 -178.76(16) . . . . ?
C10 C5 C6 C7 1.4(3) . . . . ?
C4 C5 C6 C7 -179.4(2) . . . . ?
C10 C5 C6 C1 -179.1(2) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C1 C6 C7 C8 -178.9(2) . . . . ?
C5 C6 C7 C8 0.6(3) . . . . ?
C1 C6 C7 Se2 -0.2(3) . . . . ?
C5 C6 C7 Se2 179.33(16) . . . . ?
C6 C7 C8 O2 178.2(2) . . . . ?
Se2 C7 C8 O2 -0.4(3) . . . . ?
C6 C7 C8 C9 -1.2(3) . . . . ?
Se2 C7 C8 C9 -179.89(17) . . . . ?
O2 C8 C9 C10 -179.6(2) . . . . ?
C7 C8 C9 C10 -0.2(4) . . . . ?
C8 C9 C10 C5 2.3(4) . . . . ?
C4 C5 C10 C9 178.0(2) . . . . ?
C6 C5 C10 C9 -2.8(3) . . . . ?
C2 C1 Se1 Se2 -178.39(18) . . . . ?
C6 C1 Se1 Se2 -0.80(18) . . . . ?
C6 C7 Se2 Se1 -0.30(18) . . . . ?
C8 C7 Se2 Se1 178.38(18) . . . . ?
C3 C2 O1 C11 -3.9(4) . . . . ?
C1 C2 O1 C11 175.1(2) . . . . ?
C9 C8 O2 C12 4.9(3) . . . . ?
C7 C8 O2 C12 -174.5(2) . . . . ?



# END of CIF
_chemical_name_systematic        
'(2,7-dimethoxynaphtalene peri-diselenide) tetrachloroferrate'
_exptl_crystal_recrystallization_method Electrocrystallization
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2497448'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University Rennes
France
;
_audit_update_record             
;
2025-10-23 deposited with the CCDC.	2026-03-05 downloaded from the CCDC.
;

_audit_creation_date             2024-04-18T09:10:20-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C12 H10 Cl4 Ga O2 Se2'
_chemical_formula_sum            'C12 H10 Cl4 Ga O2 Se2'
_chemical_formula_weight         555.64

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8755(12)
_cell_length_b                   10.5581(18)
_cell_length_c                   13.307(2)
_cell_angle_alpha                109.147(5)
_cell_angle_beta                 99.047(5)
_cell_angle_gamma                101.950(6)
_cell_volume                     865.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8346
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      27.48
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    2.131
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             530

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    6.408
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.688
_exptl_absorpt_correction_T_max  0.825

#------------------------------- Remark -------------------------------------#
# SADABS output:                                                             #
# Estimated minimum and maximum transmission:  0.4784  0.7456                #
# The ratio of these values is more reliable than their absolute values!     #
#----------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean 7.39
_diffrn_orient_matrix_ub_11      0.042748
_diffrn_orient_matrix_ub_12      0.091312
_diffrn_orient_matrix_ub_13      -0.009029
_diffrn_orient_matrix_ub_21      -0.12715
_diffrn_orient_matrix_ub_22      0.02227
_diffrn_orient_matrix_ub_23      0.019106
_diffrn_orient_matrix_ub_31      0.074174
_diffrn_orient_matrix_ub_32      0.045336
_diffrn_orient_matrix_ub_33      0.079251
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0842
_diffrn_reflns_av_unetI/netI     0.0646
_diffrn_reflns_number            18599
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.158
_diffrn_reflns_theta_max         27.651
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_reflns_Friedel_coverage         0
_reflns_number_total             3973
_reflns_number_gt                3290
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0610P)²+48.6661P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3973
_refine_ls_number_parameters     208
_refine_ls_number_restraints     10
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1255
_refine_ls_R_factor_gt           0.1093
_refine_ls_wR_factor_ref         0.2799
_refine_ls_wR_factor_gt          0.2712
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_restrained_S_all      1.152
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         4.05
_refine_diff_density_min         -2.5
_refine_diff_density_rms         0.339

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ga Ga 0.2307 1.6083 '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_
_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 0.292(2) 0.5559(14) 0.5922(12) 0.021(3) Uani 1 1 d . . . . .
C2 C 0.308(2) 0.5503(15) 0.6967(12) 0.024(3) Uani 1 1 d . . . . .
C3 C 0.223(2) 0.4252(16) 0.7082(12) 0.024(3) Uani 1 1 d . . . . .
H3 H 0.233275 0.420632 0.778897 0.029 Uiso 1 1 calc R U . . .
C4 C 0.124(2) 0.3073(15) 0.6143(13) 0.027(3) Uani 1 1 d . . . . .
H4 H 0.063935 0.22232 0.621769 0.032 Uiso 1 1 calc R U . . .
C5 C 0.1103(19) 0.3106(14) 0.5106(11) 0.020(3) Uani 1 1 d . . . . .
C6 C 0.017(2) 0.1942(14) 0.4102(13) 0.028(3) Uani 1 1 d . . . . .
H6 H -0.046445 0.107127 0.413385 0.034 Uiso 1 1 calc R U . . .
C7 C 0.015(2) 0.2020(16) 0.3098(14) 0.032(3) Uani 1 1 d . . . . .
H7 H -0.040207 0.119464 0.245876 0.039 Uiso 1 1 calc R U . . .
C8 C 0.092(2) 0.3303(15) 0.2989(12) 0.025(3) Uani 1 1 d . . . . .
C9 C 0.181(2) 0.4444(14) 0.3933(11) 0.020(3) Uani 1 1 d . . . . .
C10 C 0.1976(19) 0.4382(13) 0.4993(11) 0.018(2) Uani 1 1 d . . . . .
C11 C 0.454(3) 0.671(2) 0.8894(13) 0.044(4) Uani 1 1 d . . . . .
H11A H 0.32975 0.670739 0.916784 0.066 Uiso 1 1 calc R U . . .
H11B H 0.563827 0.754575 0.937366 0.066 Uiso 1 1 calc R U . . .
H11C H 0.496414 0.58758 0.888507 0.066 Uiso 1 1 calc R U . . .
C12 C 0.012(3) 0.228(2) 0.1025(14) 0.046(5) Uani 1 1 d . . . . .
H12A H 0.119124 0.181944 0.085442 0.07 Uiso 1 1 calc R U . . .
H12B H -0.035125 0.258665 0.043357 0.07 Uiso 1 1 calc R U . . .
H12C H -0.10361 0.162238 0.109748 0.07 Uiso 1 1 calc R U . . .
O1 O 0.4132(18) 0.6708(11) 0.7810(8) 0.032(2) Uani 1 1 d . . . . .
O2 O 0.0931(17) 0.3473(12) 0.2043(9) 0.031(2) Uani 1 1 d . . . . .
Se1 Se 0.4071(2) 0.72427(14) 0.57571(12) 0.0227(4) Uani 1 1 d . . . . .
Se2 Se 0.3028(2) 0.61797(15) 0.38624(12) 0.0234(4) Uani 1 1 d . . . . .
Ga1 Ga 0.4874(3) 0.83962(19) 0.20057(15) 0.0328(5) Uani 0.914(4) 1 d D . P A 1
Cl1 Cl 0.7812(8) 0.8233(5) 0.1611(4) 0.0419(11) Uani 0.914(4) 1 d D . P A 1
Cl2 Cl 0.5400(9) 0.9142(5) 0.3787(4) 0.0433(12) Uani 0.914(4) 1 d D . P A 1
Cl3 Cl 0.2640(9) 0.6382(4) 0.1266(4) 0.0399(11) Uani 0.914(4) 1 d D . P A 1
Cl4 Cl 0.3884(10) 0.9899(5) 0.1427(5) 0.0490(13) Uani 0.914(4) 1 d D . P A 1
Ga1B Ga 0.347(3) 0.8522(18) 0.2058(14) 0.0328(5) Uani 0.086(4) 1 d D . P A 2
Cl1B Cl 0.661(5) 0.839(5) 0.195(4) 0.0419(11) Uani 0.086(4) 1 d D . P A 2
Cl2B Cl 0.354(8) 0.940(4) 0.378(2) 0.0433(12) Uani 0.086(4) 1 d D . P A 2
Cl3B Cl 0.137(7) 0.648(3) 0.125(3) 0.0399(11) Uani 0.086(4) 1 d D . P A 2
Cl4B Cl 0.292(8) 0.993(4) 0.125(4) 0.0490(13) Uani 0.086(4) 1 d D . P A 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C10 1.378(19) . ?
C1 C2 1.40(2) . ?
C1 Se1 1.887(14) . ?
C2 O1 1.352(18) . ?
C2 C3 1.40(2) . ?
C3 C4 1.39(2) . ?
C3 H3 0.95 . ?
C4 C5 1.38(2) . ?
C4 H4 0.95 . ?
C5 C10 1.423(18) . ?
C5 C6 1.43(2) . ?
C6 C7 1.36(2) . ?
C6 H6 0.95 . ?
C7 C8 1.41(2) . ?
C7 H7 0.95 . ?
C8 O2 1.330(18) . ?
C8 C9 1.37(2) . ?
C9 C10 1.420(19) . ?
C9 Se2 1.890(14) . ?
C11 O1 1.425(19) . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C12 O2 1.44(2) . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
Se1 Se2 2.318(2) . ?
Ga1 Cl3 2.156(5) . ?
Ga1 Cl4 2.158(6) . ?
Ga1 Cl2 2.181(5) . ?
Ga1 Cl1 2.192(6) . ?
Ga1B Cl3B 2.142(18) . ?
Ga1B Cl4B 2.156(19) . ?
Ga1B Cl2B 2.164(18) . ?
Ga1B Cl1B 2.218(19) . ?

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
C10 C1 C2 120.9(13) . . ?
C10 C1 Se1 118.6(11) . . ?
C2 C1 Se1 120.4(11) . . ?
O1 C2 C3 124.5(13) . . ?
O1 C2 C1 115.3(12) . . ?
C3 C2 C1 120.1(13) . . ?
C4 C3 C2 118.8(13) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C5 C4 C3 121.7(13) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C10 119.2(13) . . ?
C4 C5 C6 125.4(13) . . ?
C10 C5 C6 115.3(13) . . ?
C7 C6 C5 123.0(14) . . ?
C7 C6 H6 118.5 . . ?
C5 C6 H6 118.5 . . ?
C6 C7 C8 121.4(14) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
O2 C8 C9 117.6(13) . . ?
O2 C8 C7 125.2(14) . . ?
C9 C8 C7 117.1(14) . . ?
C8 C9 C10 122.9(13) . . ?
C8 C9 Se2 119.9(11) . . ?
C10 C9 Se2 117.1(10) . . ?
C1 C10 C9 120.8(12) . . ?
C1 C10 C5 119.2(12) . . ?
C9 C10 C5 120.0(12) . . ?
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 . . ?
C2 O1 C11 119.0(13) . . ?
C8 O2 C12 119.5(13) . . ?
C1 Se1 Se2 91.5(4) . . ?
C9 Se2 Se1 92.0(4) . . ?
Cl3 Ga1 Cl4 111.2(2) . . ?
Cl3 Ga1 Cl2 110.12(19) . . ?
Cl4 Ga1 Cl2 109.4(2) . . ?
Cl3 Ga1 Cl1 110.1(2) . . ?
Cl4 Ga1 Cl1 108.7(2) . . ?
Cl2 Ga1 Cl1 107.3(2) . . ?
Cl3B Ga1B Cl4B 112.6(16) . . ?
Cl3B Ga1B Cl2B 112.4(14) . . ?
Cl4B Ga1B Cl2B 111.2(15) . . ?
Cl3B Ga1B Cl1B 109.2(15) . . ?
Cl4B Ga1B Cl1B 104.2(15) . . ?
Cl2B Ga1B Cl1B 106.8(15) . . ?

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
C10 C1 C2 O1 176.6(13) . . . . ?
Se1 C1 C2 O1 -1.3(18) . . . . ?
C10 C1 C2 C3 -2(2) . . . . ?
Se1 C1 C2 C3 -179.7(11) . . . . ?
O1 C2 C3 C4 -178.0(14) . . . . ?
C1 C2 C3 C4 0(2) . . . . ?
C2 C3 C4 C5 1(2) . . . . ?
C3 C4 C5 C10 -1(2) . . . . ?
C3 C4 C5 C6 178.1(14) . . . . ?
C4 C5 C6 C7 -177.4(15) . . . . ?
C10 C5 C6 C7 2(2) . . . . ?
C5 C6 C7 C8 -5(2) . . . . ?
C6 C7 C8 O2 -179.2(14) . . . . ?
C6 C7 C8 C9 4(2) . . . . ?
O2 C8 C9 C10 -177.0(12) . . . . ?
C7 C8 C9 C10 0(2) . . . . ?
O2 C8 C9 Se2 -0.7(18) . . . . ?
C7 C8 C9 Se2 176.2(11) . . . . ?
C2 C1 C10 C9 179.8(13) . . . . ?
Se1 C1 C10 C9 -2.3(17) . . . . ?
C2 C1 C10 C5 2(2) . . . . ?
Se1 C1 C10 C5 179.9(10) . . . . ?
C8 C9 C10 C1 179.0(13) . . . . ?
Se2 C9 C10 C1 2.6(17) . . . . ?
C8 C9 C10 C5 -3(2) . . . . ?
Se2 C9 C10 C5 -179.6(10) . . . . ?
C4 C5 C10 C1 -0.7(19) . . . . ?
C6 C5 C10 C1 -179.7(12) . . . . ?
C4 C5 C10 C9 -178.5(12) . . . . ?
C6 C5 C10 C9 2.5(19) . . . . ?
C3 C2 O1 C11 4(2) . . . . ?
C1 C2 O1 C11 -174.0(14) . . . . ?
C9 C8 O2 C12 176.3(14) . . . . ?
C7 C8 O2 C12 0(2) . . . . ?
C10 C1 Se1 Se2 0.9(10) . . . . ?
C2 C1 Se1 Se2 178.8(11) . . . . ?
C8 C9 Se2 Se1 -178.0(11) . . . . ?
C10 C9 Se2 Se1 -1.5(10) . . . . ?



# END of CIF
_chemical_name_systematic        
'(2,7-dimethoxynaphtalene peri-diselenide) tetrachlorogallate'
_exptl_crystal_recrystallization_method Electrocrystallization
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2497449'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University Rennes
France
;
_audit_update_record             
;
2025-10-23 deposited with the CCDC.	2026-03-05 downloaded from the CCDC.
;

_audit_creation_date             2024-04-16T16:18:48-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C12 H10 Cl4 Ga O2 Se2'
_chemical_formula_sum            'C12 H10 Cl4 Ga O2 Se2'
_chemical_formula_weight         555.64

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8366(8)
_cell_length_b                   13.2303(15)
_cell_length_c                   19.885(2)
_cell_angle_alpha                72.788(4)
_cell_angle_beta                 87.095(4)
_cell_angle_gamma                84.530(4)
_cell_volume                     1709.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9315
_cell_measurement_theta_min      3.15
_cell_measurement_theta_max      27.47
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_exptl_crystal_density_diffrn    2.159
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1060

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    6.49
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.586
_exptl_absorpt_correction_T_max  0.937

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.4586  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
# Ratio of Min/Max transmission:               0.6151                          #
#------------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean 7.39
_diffrn_orient_matrix_ub_11      0.095608
_diffrn_orient_matrix_ub_12      -0.048084
_diffrn_orient_matrix_ub_13      -0.018398
_diffrn_orient_matrix_ub_21      -0.102618
_diffrn_orient_matrix_ub_22      -0.008388
_diffrn_orient_matrix_ub_23      -0.031595
_diffrn_orient_matrix_ub_31      0.043961
_diffrn_orient_matrix_ub_32      0.062638
_diffrn_orient_matrix_ub_33      -0.037902
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_number            42546
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.277
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_coverage         0
_reflns_number_total             7807
_reflns_number_gt                6670
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0393P)²+4.3901P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7807
_refine_ls_number_parameters     415
_refine_ls_number_restraints     20
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.0926
_refine_ls_wR_factor_gt          0.0888
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.09
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         2.41
_refine_diff_density_min         -1.079
_refine_diff_density_rms         0.128

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ga Ga 0.2307 1.6083 '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_
_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 0.2064(5) 0.0798(3) 0.52876(19) 0.0160(7) Uani 1 1 d . . . . .
C2 C 0.1569(5) 0.1152(3) 0.5876(2) 0.0210(8) Uani 1 1 d . . . . .
C3 C 0.1132(6) 0.0415(3) 0.6524(2) 0.0255(9) Uani 1 1 d . . . . .
H3 H 0.080917 0.06461 0.692779 0.031 Uiso 1 1 calc R U . . .
C4 C 0.1176(6) -0.0651(3) 0.6567(2) 0.0247(9) Uani 1 1 d . . . . .
H4 H 0.084152 -0.113985 0.70047 0.03 Uiso 1 1 calc R U . . .
C5 C 0.1692(5) -0.1040(3) 0.5993(2) 0.0206(8) Uani 1 1 d . . . . .
C6 C 0.1781(5) -0.2114(3) 0.6017(2) 0.0220(8) Uani 1 1 d . . . . .
H6 H 0.145005 -0.262434 0.64451 0.026 Uiso 1 1 calc R U . . .
C7 C 0.2339(6) -0.2452(3) 0.5431(2) 0.0230(8) Uani 1 1 d . . . . .
H7 H 0.240688 -0.318618 0.546634 0.028 Uiso 1 1 calc R U . . .
C8 C 0.2803(5) -0.1714(3) 0.4789(2) 0.0206(8) Uani 1 1 d . . . . .
C9 C 0.2668(5) -0.0628(3) 0.4747(2) 0.0163(7) Uani 1 1 d . . . . .
C10 C 0.2134(5) -0.0285(3) 0.53371(19) 0.0168(7) Uani 1 1 d . . . . .
C11 C 0.1213(8) 0.2612(4) 0.6367(3) 0.0399(12) Uani 1 1 d . . . . .
H11A H -0.008591 0.243144 0.65736 0.06 Uiso 1 1 calc R U . . .
H11B H 0.12502 0.338557 0.621194 0.06 Uiso 1 1 calc R U . . .
H11C H 0.221875 0.229594 0.671992 0.06 Uiso 1 1 calc R U . . .
C12 C 0.3771(7) -0.3047(4) 0.4227(3) 0.0372(11) Uani 1 1 d . . . . .
H12A H 0.47983 -0.338583 0.45668 0.056 Uiso 1 1 calc R U . . .
H12B H 0.420406 -0.309832 0.375966 0.056 Uiso 1 1 calc R U . . .
H12C H 0.256306 -0.34067 0.437165 0.056 Uiso 1 1 calc R U . . .
C13 C 0.2114(5) 0.5783(3) 0.02753(19) 0.0163(7) Uani 1 1 d . . . . .
C14 C 0.1658(5) 0.6872(3) 0.0199(2) 0.0214(8) Uani 1 1 d . . . . .
C15 C 0.1138(6) 0.7552(3) -0.0463(2) 0.0249(8) Uani 1 1 d . . . . .
H15 H 0.082075 0.828708 -0.052187 0.03 Uiso 1 1 calc R U . . .
C16 C 0.1082(6) 0.7160(3) -0.1033(2) 0.0244(8) Uani 1 1 d . . . . .
H16 H 0.06785 0.763203 -0.147417 0.029 Uiso 1 1 calc R U . . .
C17 C 0.1600(5) 0.6088(3) -0.0983(2) 0.0203(8) Uani 1 1 d . . . . .
C18 C 0.1618(6) 0.5651(3) -0.1548(2) 0.0230(8) Uani 1 1 d . . . . .
H18 H 0.124763 0.609902 -0.200032 0.028 Uiso 1 1 calc R U . . .
C19 C 0.2159(6) 0.4587(4) -0.1466(2) 0.0250(9) Uani 1 1 d . . . . .
H19 H 0.218095 0.432108 -0.18605 0.03 Uiso 1 1 calc R U . . .
C20 C 0.2673(5) 0.3904(3) -0.0807(2) 0.0202(8) Uani 1 1 d . . . . .
C21 C 0.2624(5) 0.4310(3) -0.0225(2) 0.0177(7) Uani 1 1 d . . . . .
C22 C 0.2111(5) 0.5385(3) -0.03043(19) 0.0159(7) Uani 1 1 d . . . . .
C23 C 0.1512(7) 0.8279(4) 0.0733(3) 0.0362(11) Uani 1 1 d . . . . .
H23A H 0.245381 0.866233 0.038528 0.054 Uiso 1 1 calc R U . . .
H23B H 0.173189 0.837574 0.119284 0.054 Uiso 1 1 calc R U . . .
H23C H 0.017075 0.855661 0.05865 0.054 Uiso 1 1 calc R U . . .
C24 C 0.3549(7) 0.2431(4) -0.1254(3) 0.0374(11) Uani 1 1 d . . . . .
H24A H 0.232747 0.254004 -0.151292 0.056 Uiso 1 1 calc R U . . .
H24B H 0.394086 0.166844 -0.107682 0.056 Uiso 1 1 calc R U . . .
H24C H 0.458711 0.278539 -0.156877 0.056 Uiso 1 1 calc R U . . .
O1 O 0.1593(4) 0.2203(2) 0.57694(16) 0.0273(6) Uani 1 1 d . . . . .
O2 O 0.3399(4) -0.1948(2) 0.42005(15) 0.0253(6) Uani 1 1 d . . . . .
O3 O 0.1777(4) 0.7160(2) 0.07860(15) 0.0253(6) Uani 1 1 d . . . . .
O4 O 0.3243(4) 0.2870(2) -0.06680(16) 0.0270(6) Uani 1 1 d . . . . .
Se1 Se 0.26847(5) 0.17494(3) 0.44207(2) 0.02001(9) Uani 1 1 d . . . . .
Se2 Se 0.32949(5) 0.03880(3) 0.39025(2) 0.01967(9) Uani 1 1 d . . . . .
Se3 Se 0.28453(5) 0.48368(3) 0.11442(2) 0.01995(9) Uani 1 1 d . . . . .
Se4 Se 0.33485(5) 0.34275(3) 0.06654(2) 0.01999(9) Uani 1 1 d . . . . .
Ga1 Ga 0.31307(11) 0.47931(4) 0.32606(2) 0.02832(16) Uani 0.9754(16) 1 d D . P
A 1
Cl1 Cl 0.2895(3) 0.34328(10) 0.28626(7) 0.0566(5) Uani 0.9754(16) 1 d D . P A 1
Cl2 Cl 0.6213(2) 0.50202(11) 0.33268(7) 0.0462(3) Uani 0.9754(16) 1 d D . P A 1
Cl3 Cl 0.1710(2) 0.61823(9) 0.25223(6) 0.0360(3) Uani 0.9754(16) 1 d D . P A 1
Cl4 Cl 0.1729(2) 0.44639(9) 0.42981(6) 0.0376(3) Uani 0.9754(16) 1 d D . P A 1
Ga1A Ga 0.433(4) 0.4748(14) 0.3258(9) 0.02832(16) Uani 0.0246(16) 1 d D . P A 2
Cl1A Cl 0.428(10) 0.340(3) 0.285(2) 0.0566(5) Uani 0.0246(16) 1 d D . P A 2
Cl2A Cl 0.730(5) 0.509(4) 0.333(3) 0.0462(3) Uani 0.0246(16) 1 d D . P A 2
Cl3A Cl 0.265(7) 0.608(3) 0.253(2) 0.0360(3) Uani 0.0246(16) 1 d D . P A 2
Cl4A Cl 0.277(8) 0.440(4) 0.4273(16) 0.0376(3) Uani 0.0246(16) 1 d D . P A 2
Ga2 Ga 0.52813(7) 0.02572(4) 0.17408(2) 0.02501(12) Uani 0.9872(9) 1 d D . P B
3
Cl5 Cl 0.48967(19) 0.16085(9) 0.21677(6) 0.0350(3) Uani 0.9872(9) 1 d D . P B 3
Cl6 Cl 0.84200(17) -0.01520(9) 0.16390(6) 0.0334(2) Uani 0.9872(9) 1 d D . P B
3
Cl7 Cl 0.3920(2) -0.10780(10) 0.24534(7) 0.0423(3) Uani 0.9872(9) 1 d D . P B 3
Cl8 Cl 0.39778(19) 0.06956(9) 0.07102(6) 0.0358(3) Uani 0.9872(9) 1 d D . P B 3
Ga2B Ga 0.695(5) 0.019(2) 0.1729(15) 0.02501(12) Uani 0.0128(9) 1 d D . P B 4
Cl5B Cl 0.422(7) 0.112(5) 0.185(3) 0.0350(3) Uani 0.0128(9) 1 d D . P B 4
Cl6B Cl 0.904(8) 0.038(6) 0.247(3) 0.0334(2) Uani 0.0128(9) 1 d D . P B 4
Cl7B Cl 0.643(11) -0.148(3) 0.200(4) 0.0423(3) Uani 0.0128(9) 1 d D . P B 4
Cl8B Cl 0.805(10) 0.072(5) 0.0652(19) 0.0358(3) Uani 0.0128(9) 1 d D . P B 4



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C2 1.399(5) . ?
C1 C10 1.402(5) . ?
C1 Se1 1.865(4) . ?
C2 O1 1.346(5) . ?
C2 C3 1.403(6) . ?
C3 C4 1.386(6) . ?
C3 Cl6B 1.97(6) 2_656 ?
C3 H3 0.95 . ?
C4 C5 1.402(6) . ?
C4 Cl6B 2.05(5) 2_656 ?
C4 H4 0.95 . ?
C5 C6 1.403(6) . ?
C5 C10 1.427(5) . ?
C6 C7 1.390(6) . ?
C6 H6 0.95 . ?
C7 C8 1.401(6) . ?
C7 H7 0.95 . ?
C8 O2 1.333(5) . ?
C8 C9 1.408(5) . ?
C9 C10 1.399(5) . ?
C9 Se2 1.874(4) . ?
C11 O1 1.447(5) . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C12 O2 1.438(5) . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 C22 1.402(5) . ?
C13 C14 1.409(5) . ?
C13 Se3 1.868(4) . ?
C14 O3 1.338(5) . ?
C14 C15 1.399(6) . ?
C15 C16 1.383(6) . ?
C15 H15 0.95 . ?
C16 C17 1.403(6) . ?
C16 H16 0.95 . ?
C17 C18 1.407(6) . ?
C17 C22 1.433(5) . ?
C18 C19 1.383(6) . ?
C18 H18 0.95 . ?
C19 C20 1.393(6) . ?
C19 H19 0.95 . ?
C20 O4 1.336(5) . ?
C20 C21 1.409(5) . ?
C21 C22 1.396(5) . ?
C21 Se4 1.871(4) . ?
C23 O3 1.447(5) . ?
C23 H23A 0.98 . ?
C23 H23B 0.98 . ?
C23 H23C 0.98 . ?
C24 O4 1.447(5) . ?
C24 Cl7B 2.20(6) 2_655 ?
C24 H24A 0.98 . ?
C24 H24B 0.98 . ?
C24 H24C 0.98 . ?
Se1 Se2 2.3220(6) . ?
Se3 Se4 2.3230(6) . ?
Ga1 Cl3 2.1643(13) . ?
Ga1 Cl4 2.1705(13) . ?
Ga1 Cl2 2.1724(16) . ?
Ga1 Cl1 2.1913(13) . ?
Ga1A Cl2A 2.142(18) . ?
Ga1A Cl4A 2.177(18) . ?
Ga1A Cl1A 2.181(18) . ?
Ga1A Cl3A 2.187(18) . ?
Ga2 Cl7 2.1661(13) . ?
Ga2 Cl8 2.1710(12) . ?
Ga2 Cl6 2.1766(12) . ?
Ga2 Cl5 2.1845(12) . ?
Ga2B Cl8B 2.168(19) . ?
Ga2B Cl6B 2.178(19) . ?
Ga2B Cl5B 2.180(19) . ?
Ga2B Cl7B 2.180(19) . ?

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
C2 C1 C10 120.8(3) . . ?
C2 C1 Se1 120.9(3) . . ?
C10 C1 Se1 118.3(3) . . ?
O1 C2 C1 115.5(4) . . ?
O1 C2 C3 124.9(4) . . ?
C1 C2 C3 119.6(4) . . ?
C4 C3 C2 119.4(4) . . ?
C4 C3 Cl6B 72.9(18) . 2_656 ?
C2 C3 Cl6B 164.1(15) . 2_656 ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
Cl6B C3 H3 48.5 2_656 . ?
C3 C4 C5 122.8(4) . . ?
C3 C4 Cl6B 67(2) . 2_656 ?
C5 C4 Cl6B 165.2(18) . 2_656 ?
C3 C4 H4 118.6 . . ?
C5 C4 H4 118.6 . . ?
Cl6B C4 H4 53.2 2_656 . ?
C4 C5 C6 124.6(4) . . ?
C4 C5 C10 117.4(4) . . ?
C6 C5 C10 118.0(4) . . ?
C7 C6 C5 121.9(4) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C6 C7 C8 120.3(4) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
O2 C8 C7 125.4(4) . . ?
O2 C8 C9 115.7(4) . . ?
C7 C8 C9 118.9(4) . . ?
C10 C9 C8 121.1(4) . . ?
C10 C9 Se2 118.4(3) . . ?
C8 C9 Se2 120.5(3) . . ?
C9 C10 C1 120.1(3) . . ?
C9 C10 C5 119.8(4) . . ?
C1 C10 C5 120.1(4) . . ?
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 . . ?
C22 C13 C14 121.0(3) . . ?
C22 C13 Se3 118.0(3) . . ?
C14 C13 Se3 120.9(3) . . ?
O3 C14 C15 125.7(4) . . ?
O3 C14 C13 115.4(4) . . ?
C15 C14 C13 118.9(4) . . ?
C16 C15 C14 120.4(4) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 122.3(4) . . ?
C15 C16 H16 118.9 . . ?
C17 C16 H16 118.9 . . ?
C16 C17 C18 124.8(4) . . ?
C16 C17 C22 117.6(4) . . ?
C18 C17 C22 117.6(4) . . ?
C19 C18 C17 122.0(4) . . ?
C19 C18 H18 119 . . ?
C17 C18 H18 119 . . ?
C18 C19 C20 120.4(4) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
O4 C20 C19 125.6(4) . . ?
O4 C20 C21 115.3(4) . . ?
C19 C20 C21 119.2(4) . . ?
C22 C21 C20 120.9(4) . . ?
C22 C21 Se4 118.4(3) . . ?
C20 C21 Se4 120.6(3) . . ?
C21 C22 C13 120.4(3) . . ?
C21 C22 C17 119.8(3) . . ?
C13 C22 C17 119.7(3) . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O4 C24 Cl7B 166.6(14) . 2_655 ?
O4 C24 H24A 109.5 . . ?
Cl7B C24 H24A 66.6 2_655 . ?
O4 C24 H24B 109.5 . . ?
Cl7B C24 H24B 62.2 2_655 . ?
H24A C24 H24B 109.5 . . ?
O4 C24 H24C 109.5 . . ?
Cl7B C24 H24C 83.7 2_655 . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C2 O1 C11 118.2(4) . . ?
C8 O2 C12 118.5(4) . . ?
C14 O3 C23 118.4(4) . . ?
C20 O4 C24 118.1(4) . . ?
C1 Se1 Se2 91.84(12) . . ?
C9 Se2 Se1 91.38(12) . . ?
C13 Se3 Se4 91.80(12) . . ?
C21 Se4 Se3 91.43(12) . . ?
Cl3 Ga1 Cl4 111.81(6) . . ?
Cl3 Ga1 Cl2 109.48(6) . . ?
Cl4 Ga1 Cl2 109.99(6) . . ?
Cl3 Ga1 Cl1 107.78(6) . . ?
Cl4 Ga1 Cl1 108.36(5) . . ?
Cl2 Ga1 Cl1 109.35(7) . . ?
Cl2A Ga1A Cl4A 111.9(15) . . ?
Cl2A Ga1A Cl1A 110.2(16) . . ?
Cl4A Ga1A Cl1A 108.9(15) . . ?
Cl2A Ga1A Cl3A 111.7(15) . . ?
Cl4A Ga1A Cl3A 107.5(15) . . ?
Cl1A Ga1A Cl3A 106.5(15) . . ?
Cl7 Ga2 Cl8 110.59(5) . . ?
Cl7 Ga2 Cl6 109.81(5) . . ?
Cl8 Ga2 Cl6 109.37(5) . . ?
Cl7 Ga2 Cl5 109.48(5) . . ?
Cl8 Ga2 Cl5 109.51(5) . . ?
Cl6 Ga2 Cl5 108.04(5) . . ?
Cl8B Ga2B Cl6B 111.6(17) . . ?
Cl8B Ga2B Cl5B 110.1(17) . . ?
Cl6B Ga2B Cl5B 107.7(16) . . ?
Cl8B Ga2B Cl7B 109.3(17) . . ?
Cl6B Ga2B Cl7B 108.5(17) . . ?
Cl5B Ga2B Cl7B 109.6(17) . . ?
C3 Cl6B C4 40.2(11) 2_656 2_656 ?
C3 Cl6B Ga2B 121(3) 2_656 . ?
C4 Cl6B Ga2B 135(3) 2_656 . ?

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
C10 C1 C2 O1 178.6(3) . . . . ?
Se1 C1 C2 O1 -0.5(5) . . . . ?
C10 C1 C2 C3 -0.2(5) . . . . ?
Se1 C1 C2 C3 -179.3(3) . . . . ?
O1 C2 C3 C4 -179.4(4) . . . . ?
C1 C2 C3 C4 -0.7(6) . . . . ?
O1 C2 C3 Cl6B -41(7) . . . 2_656 ?
C1 C2 C3 Cl6B 138(7) . . . 2_656 ?
C2 C3 C4 C5 1.7(6) . . . . ?
Cl6B C3 C4 C5 -167.3(17) 2_656 . . . ?
C2 C3 C4 Cl6B 169.0(17) . . . 2_656 ?
C3 C4 C5 C6 179.1(4) . . . . ?
Cl6B C4 C5 C6 51(7) 2_656 . . . ?
C3 C4 C5 C10 -1.7(6) . . . . ?
Cl6B C4 C5 C10 -129(7) 2_656 . . . ?
C4 C5 C6 C7 -178.8(4) . . . . ?
C10 C5 C6 C7 2.0(5) . . . . ?
C5 C6 C7 C8 -1.1(6) . . . . ?
C6 C7 C8 O2 178.3(4) . . . . ?
C6 C7 C8 C9 -0.8(5) . . . . ?
O2 C8 C9 C10 -177.5(3) . . . . ?
C7 C8 C9 C10 1.7(5) . . . . ?
O2 C8 C9 Se2 0.2(5) . . . . ?
C7 C8 C9 Se2 179.5(3) . . . . ?
C8 C9 C10 C1 178.1(3) . . . . ?
Se2 C9 C10 C1 0.4(5) . . . . ?
C8 C9 C10 C5 -0.7(5) . . . . ?
Se2 C9 C10 C5 -178.5(3) . . . . ?
C2 C1 C10 C9 -178.7(3) . . . . ?
Se1 C1 C10 C9 0.4(5) . . . . ?
C2 C1 C10 C5 0.1(5) . . . . ?
Se1 C1 C10 C5 179.3(3) . . . . ?
C4 C5 C10 C9 179.7(3) . . . . ?
C6 C5 C10 C9 -1.1(5) . . . . ?
C4 C5 C10 C1 0.8(5) . . . . ?
C6 C5 C10 C1 -180.0(3) . . . . ?
C22 C13 C14 O3 -177.8(3) . . . . ?
Se3 C13 C14 O3 -0.4(5) . . . . ?
C22 C13 C14 C15 2.0(5) . . . . ?
Se3 C13 C14 C15 179.4(3) . . . . ?
O3 C14 C15 C16 179.5(4) . . . . ?
C13 C14 C15 C16 -0.3(6) . . . . ?
C14 C15 C16 C17 -2.2(6) . . . . ?
C15 C16 C17 C18 -178.3(4) . . . . ?
C15 C16 C17 C22 2.9(6) . . . . ?
C16 C17 C18 C19 179.5(4) . . . . ?
C22 C17 C18 C19 -1.8(5) . . . . ?
C17 C18 C19 C20 1.3(6) . . . . ?
C18 C19 C20 O4 -179.0(4) . . . . ?
C18 C19 C20 C21 0.3(6) . . . . ?
O4 C20 C21 C22 178.1(3) . . . . ?
C19 C20 C21 C22 -1.3(5) . . . . ?
O4 C20 C21 Se4 0.6(5) . . . . ?
C19 C20 C21 Se4 -178.8(3) . . . . ?
C20 C21 C22 C13 -178.4(3) . . . . ?
Se4 C21 C22 C13 -0.9(5) . . . . ?
C20 C21 C22 C17 0.8(5) . . . . ?
Se4 C21 C22 C17 178.3(3) . . . . ?
C14 C13 C22 C21 178.0(3) . . . . ?
Se3 C13 C22 C21 0.6(5) . . . . ?
C14 C13 C22 C17 -1.2(5) . . . . ?
Se3 C13 C22 C17 -178.7(3) . . . . ?
C16 C17 C22 C21 179.6(3) . . . . ?
C18 C17 C22 C21 0.8(5) . . . . ?
C16 C17 C22 C13 -1.2(5) . . . . ?
C18 C17 C22 C13 180.0(3) . . . . ?
C1 C2 O1 C11 -176.3(3) . . . . ?
C3 C2 O1 C11 2.4(6) . . . . ?
C7 C8 O2 C12 -5.7(6) . . . . ?
C9 C8 O2 C12 173.4(3) . . . . ?
C15 C14 O3 C23 -5.6(6) . . . . ?
C13 C14 O3 C23 174.2(3) . . . . ?
C19 C20 O4 C24 6.6(6) . . . . ?
C21 C20 O4 C24 -172.8(3) . . . . ?
Cl7B C24 O4 C20 -130(8) 2_655 . . . ?
C2 C1 Se1 Se2 178.4(3) . . . . ?
C10 C1 Se1 Se2 -0.7(3) . . . . ?
C10 C9 Se2 Se1 -0.7(3) . . . . ?
C8 C9 Se2 Se1 -178.5(3) . . . . ?
C22 C13 Se3 Se4 0.0(3) . . . . ?
C14 C13 Se3 Se4 -177.5(3) . . . . ?
C22 C21 Se4 Se3 0.7(3) . . . . ?
C20 C21 Se4 Se3 178.2(3) . . . . ?



# END of CIF
_chemical_name_systematic        
'(2,7-dimethoxynaphtalene peri-diselenide) tetrachlorogallate'
_exptl_crystal_recrystallization_method Electrocrystallization
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2497451'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University Rennes
France
;
_audit_update_record             
;
2025-10-23 deposited with the CCDC.	2026-03-05 downloaded from the CCDC.
;

_audit_creation_date             2025-02-14T17:32:24-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C12 H10 O2 Se2, Br4 Ga'
_chemical_formula_sum            'C12 H10 Br4 Ga O2 Se2'
_chemical_formula_weight         733.48

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
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'

_cell_length_a                   6.9210(9)
_cell_length_b                   24.702(3)
_cell_length_c                   10.9454(11)
_cell_angle_alpha                90
_cell_angle_beta                 102.557(5)
_cell_angle_gamma                90
_cell_volume                     1826.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3906
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      27.43
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    2.667
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1348

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    14.241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2012). TWINABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.430
_exptl_absorpt_correction_T_max  0.752

#-------------------------------- Remark --------------------------------------#
# TWINABS output:                                                              #
# Minimum and maximum apparent transmission:  0.339565  0.745553               #
# The ratio of these values is more reliable than their absolute values!       #
# Ratio of Min/Max transmission:               0.4555                          #
#------------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean 7.39
_diffrn_orient_matrix_ub_11      0.11523
_diffrn_orient_matrix_ub_12      0.022289
_diffrn_orient_matrix_ub_13      0.043388
_diffrn_orient_matrix_ub_21      -0.086777
_diffrn_orient_matrix_ub_22      0.032765
_diffrn_orient_matrix_ub_23      -0.008683
_diffrn_orient_matrix_ub_31      -0.033227
_diffrn_orient_matrix_ub_32      -0.008275
_diffrn_orient_matrix_ub_33      0.082482
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_number            4155
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.077
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.989
_reflns_Friedel_coverage         0
_reflns_number_total             4155
_reflns_number_gt                3767
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0128P)²+8.1822P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4155
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.045
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.0756
_refine_ls_wR_factor_gt          0.0739
_refine_ls_goodness_of_fit_ref   1.189
_refine_ls_restrained_S_all      1.189
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.847
_refine_diff_density_min         -0.772
_refine_diff_density_rms         0.166

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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'
Ga Ga 0.2307 1.6083 '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'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.7515(7) 0.5460(2) 0.5000(5) 0.0151(11) Uani 1 1 d . . . . .
C2 C 0.7869(8) 0.5934(2) 0.5730(5) 0.0175(11) Uani 1 1 d . . . . .
C3 C 0.8743(8) 0.5897(2) 0.7005(5) 0.0198(12) Uani 1 1 d . . . . .
H3 H 0.895692 0.621464 0.750651 0.024 Uiso 1 1 calc R U . . .
C4 C 0.9300(8) 0.5393(2) 0.7539(5) 0.0192(12) Uani 1 1 d . . . . .
H4 H 0.994338 0.537485 0.839769 0.023 Uiso 1 1 calc R U . . .
C5 C 0.8939(7) 0.4910(2) 0.6843(5) 0.0160(11) Uani 1 1 d . . . . .
C6 C 0.9435(8) 0.4392(2) 0.7341(5) 0.0182(12) Uani 1 1 d . . . . .
H6 H 1.009019 0.435956 0.819591 0.022 Uiso 1 1 calc R U . . .
C7 C 0.9002(8) 0.3931(2) 0.6632(5) 0.0191(11) Uani 1 1 d . . . . .
H7 H 0.932438 0.35867 0.700763 0.023 Uiso 1 1 calc R U . . .
C8 C 0.8089(8) 0.3964(2) 0.5359(5) 0.0170(11) Uani 1 1 d . . . . .
C9 C 0.7624(8) 0.4482(2) 0.4819(5) 0.0155(11) Uani 1 1 d . . . . .
C10 C 0.8021(7) 0.4949(2) 0.5548(5) 0.0148(11) Uani 1 1 d . . . . .
C11 C 0.7420(11) 0.6895(2) 0.5809(6) 0.0301(15) Uani 1 1 d . . . . .
H11A H 0.659917 0.687021 0.643202 0.045 Uiso 1 1 calc R U . . .
H11B H 0.695768 0.719651 0.523772 0.045 Uiso 1 1 calc R U . . .
H11C H 0.880163 0.695722 0.623343 0.045 Uiso 1 1 calc R U . . .
C12 C 0.7919(11) 0.3011(2) 0.5102(6) 0.0285(14) Uani 1 1 d . . . . .
H12A H 0.930777 0.297407 0.553848 0.043 Uiso 1 1 calc R U . . .
H12B H 0.761031 0.274272 0.442903 0.043 Uiso 1 1 calc R U . . .
H12C H 0.706326 0.295278 0.56951 0.043 Uiso 1 1 calc R U . . .
Br1 Br 0.40324(11) 0.68357(3) -0.15361(6) 0.03452(17) Uani 1 1 d . . . . .
Br2 Br -0.01367(9) 0.66724(3) 0.01546(6) 0.02768(15) Uani 1 1 d . . . . .
Br3 Br 0.36355(9) 0.55535(2) 0.02851(5) 0.02588(14) Uani 1 1 d . . . . .
Br4 Br 0.51807(10) 0.68574(3) 0.20533(5) 0.02712(15) Uani 1 1 d . . . . .
Ga1 Ga 0.31976(10) 0.64920(3) 0.02545(6) 0.01894(14) Uani 1 1 d . . . . .
Se1 Se 0.62770(8) 0.54914(2) 0.33023(5) 0.01648(12) Uani 1 1 d . . . . .
Se2 Se 0.63967(8) 0.45561(2) 0.31216(5) 0.01649(12) Uani 1 1 d . . . . .
O1 O 0.7275(6) 0.63949(16) 0.5105(4) 0.0235(9) Uani 1 1 d . . . . .
O2 O 0.7592(6) 0.35458(16) 0.4580(4) 0.0231(9) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C2 1.409(8) . ?
C1 C10 1.409(7) . ?
C1 Se1 1.871(5) . ?
C2 O1 1.346(7) . ?
C2 C3 1.398(8) . ?
C3 C4 1.393(8) . ?
C3 H3 0.95 . ?
C4 C5 1.408(8) . ?
C4 H4 0.95 . ?
C5 C6 1.403(8) . ?
C5 C10 1.425(7) . ?
C6 C7 1.375(8) . ?
C6 H6 0.95 . ?
C7 C8 1.401(8) . ?
C7 H7 0.95 . ?
C8 O2 1.336(7) . ?
C8 C9 1.417(8) . ?
C9 C10 1.396(7) . ?
C9 Se2 1.877(5) . ?
C11 O1 1.448(7) . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C12 O2 1.437(7) . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
Br1 Ga1 2.3212(9) . ?
Br2 Ga1 2.3295(9) . ?
Br3 Ga1 2.3374(9) . ?
Br4 Ga1 2.3238(9) . ?
Se1 Se2 2.3219(8) . ?

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
C2 C1 C10 120.5(5) . . ?
C2 C1 Se1 121.0(4) . . ?
C10 C1 Se1 118.5(4) . . ?
O1 C2 C3 125.5(5) . . ?
O1 C2 C1 114.7(5) . . ?
C3 C2 C1 119.8(5) . . ?
C4 C3 C2 119.8(5) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 122.0(5) . . ?
C3 C4 H4 119 . . ?
C5 C4 H4 119 . . ?
C6 C5 C4 124.2(5) . . ?
C6 C5 C10 117.8(5) . . ?
C4 C5 C10 117.9(5) . . ?
C7 C6 C5 122.1(5) . . ?
C7 C6 H6 119 . . ?
C5 C6 H6 119 . . ?
C6 C7 C8 120.6(5) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
O2 C8 C7 126.0(5) . . ?
O2 C8 C9 115.3(5) . . ?
C7 C8 C9 118.6(5) . . ?
C10 C9 C8 120.6(5) . . ?
C10 C9 Se2 118.4(4) . . ?
C8 C9 Se2 120.9(4) . . ?
C9 C10 C1 119.9(5) . . ?
C9 C10 C5 120.2(5) . . ?
C1 C10 C5 120.0(5) . . ?
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 . . ?
Br1 Ga1 Br4 111.33(4) . . ?
Br1 Ga1 Br2 108.44(4) . . ?
Br4 Ga1 Br2 111.23(4) . . ?
Br1 Ga1 Br3 108.64(4) . . ?
Br4 Ga1 Br3 108.80(3) . . ?
Br2 Ga1 Br3 108.33(3) . . ?
C1 Se1 Se2 91.51(17) . . ?
C9 Se2 Se1 91.71(17) . . ?
C2 O1 C11 118.2(5) . . ?
C8 O2 C12 117.4(5) . . ?

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
C10 C1 C2 O1 -178.4(5) . . . . ?
Se1 C1 C2 O1 -0.9(7) . . . . ?
C10 C1 C2 C3 0.6(8) . . . . ?
Se1 C1 C2 C3 178.1(4) . . . . ?
O1 C2 C3 C4 -179.7(5) . . . . ?
C1 C2 C3 C4 1.5(8) . . . . ?
C2 C3 C4 C5 -2.6(9) . . . . ?
C3 C4 C5 C6 -178.7(5) . . . . ?
C3 C4 C5 C10 1.7(8) . . . . ?
C4 C5 C6 C7 178.1(5) . . . . ?
C10 C5 C6 C7 -2.2(8) . . . . ?
C5 C6 C7 C8 1.9(9) . . . . ?
C6 C7 C8 O2 -179.7(5) . . . . ?
C6 C7 C8 C9 0.1(8) . . . . ?
O2 C8 C9 C10 178.2(5) . . . . ?
C7 C8 C9 C10 -1.6(8) . . . . ?
O2 C8 C9 Se2 -0.1(7) . . . . ?
C7 C8 C9 Se2 -179.9(4) . . . . ?
C8 C9 C10 C1 -178.8(5) . . . . ?
Se2 C9 C10 C1 -0.5(7) . . . . ?
C8 C9 C10 C5 1.3(8) . . . . ?
Se2 C9 C10 C5 179.6(4) . . . . ?
C2 C1 C10 C9 178.6(5) . . . . ?
Se1 C1 C10 C9 1.0(7) . . . . ?
C2 C1 C10 C5 -1.5(8) . . . . ?
Se1 C1 C10 C5 -179.1(4) . . . . ?
C6 C5 C10 C9 0.6(8) . . . . ?
C4 C5 C10 C9 -179.7(5) . . . . ?
C6 C5 C10 C1 -179.3(5) . . . . ?
C4 C5 C10 C1 0.4(8) . . . . ?
C2 C1 Se1 Se2 -178.4(4) . . . . ?
C10 C1 Se1 Se2 -0.9(4) . . . . ?
C10 C9 Se2 Se1 -0.1(4) . . . . ?
C8 C9 Se2 Se1 178.2(4) . . . . ?
C3 C2 O1 C11 -4.4(8) . . . . ?
C1 C2 O1 C11 174.5(5) . . . . ?
C7 C8 O2 C12 3.6(8) . . . . ?
C9 C8 O2 C12 -176.2(5) . . . . ?



# END of CIF
_chemical_name_systematic        
'(2,7-dimethoxynaphtalene peri-diselenide) tetrachlorogallate'
_exptl_crystal_recrystallization_method Electrocrystallization
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2497450'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University Rennes
France
;
_audit_update_record             
;
2025-10-23 deposited with the CCDC.	2026-03-05 downloaded from the CCDC.
;

_audit_creation_date             2025-01-22T14:13:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C12 H10 Br4 Fe O2 Se2'
_chemical_formula_moiety         'C12 H10 O2 Se2, Br4 Fe'
_chemical_formula_weight         719.61

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
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'

_cell_length_a                   6.9157(5)
_cell_length_b                   24.6933(19)
_cell_length_c                   10.9028(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.701(3)
_cell_angle_gamma                90
_cell_volume                     1816.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9888
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      27.47
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    2.632
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1328

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    13.636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.446
_exptl_absorpt_correction_T_max  0.761

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.4727  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
# Ratio of Min/Max transmission:               0.6340                          #
#------------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean 7.39
_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_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_number            20229
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.129
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_coverage         0
_reflns_number_total             4144
_reflns_number_gt                3613
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0207P)²+5.3018P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4144
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.0682
_refine_ls_wR_factor_gt          0.0661
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.686
_refine_diff_density_min         -1.033
_refine_diff_density_rms         0.145

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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_
_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 . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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_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_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) . . . . ?



# END of CIF
