# Electronic Supplementary Material (ESI) for Faraday Discussions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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 2213815'
loop_
_audit_author_name
_audit_author_address
'Atash Gurbanov'
;Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2023-01-05 deposited with the CCDC.	2023-01-06 downloaded from the CCDC.
;

# start Validation Reply Form                                                                                                           
_vrf_PLAT431_shelx               
;                                                                                                                                       
PROBLEM:  Short Inter HL..A Contact Br1 ..Se1 . 3.28 Ang. 2-x,-y,1-z = 2_756 Check                                                          
          Short Inter HL..A Contact Br1 ..Se1 . 3.33 Ang. -1+x,y,z = 1_455 Check                                                                    
RESPONSE: The B Alert draw attention to the possibility of missed hydrogen bonds as indicated by short Donor - Acceptor atom distances. 
In the structures of the present work placing H atoms on the marked atoms is not reasonable at all and the warnings are just            
indicative of the Non-Covalent Interactions between the involved atoms.                                                                 
;
# end Validation Reply Form                                                                                                             


_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H8 Br2 Cu N8 O2 Se2'
_chemical_formula_sum            'C10 H8 Br2 Cu N8 O2 Se2'
_chemical_formula_weight         653.52

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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.4742(15)
_cell_length_b                   7.767(2)
_cell_length_c                   11.921(4)
_cell_angle_alpha                73.520(8)
_cell_angle_beta                 79.658(8)
_cell_angle_gamma                70.146(7)
_cell_volume                     455.2(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2042
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      23.28

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.384
_exptl_crystal_F_000             307
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    9.609
_shelx_estimated_absorpt_T_min   0.277
_shelx_estimated_absorpt_T_max   0.514
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.152
_exptl_absorpt_correction_T_max  0.695
_exptl_absorpt_process_details   'SADABS (Bruker, 2003)'

_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14092
_diffrn_reflns_av_unetI/netI     0.0662
_diffrn_reflns_av_R_equivalents  0.1352
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.873
_diffrn_reflns_theta_max         25.345
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1681
_reflns_number_gt                1145
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0067P)²+3.8470P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1681
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1013
_refine_ls_wR_factor_gt          0.0894
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Cu1 Cu 0.500000 0.500000 0.500000 0.0348(4) Uani 1 2 d S . P . .
Se1 Se 1.08544(18) 0.02299(14) 0.63271(10) 0.0466(3) Uani 1 1 d . . . . .
Br1 Br 0.35504(18) 0.29431(14) 0.41259(9) 0.0445(3) Uani 1 1 d . . . . .
O1 O 0.2268(13) 0.2437(10) 0.8288(6) 0.0566(19) Uani 1 1 d . . . . .
N1 N 0.2845(14) 0.4414(11) 0.6439(7) 0.0365(19) Uani 1 1 d . . . . .
H1N H 0.150(17) 0.517(13) 0.657(8) 0.044 Uiso 1 1 d . U . . .
N2 N 0.7823(13) 0.2131(10) 0.6272(6) 0.0357(18) Uani 1 1 d . . . . .
N3 N 0.9636(15) -0.1231(11) 0.7575(8) 0.053(2) Uani 1 1 d . . . . .
N4 N 0.463(2) -0.2027(16) 0.9565(10) 0.093(4) Uani 1 1 d . . . . .
C1 C 0.3567(17) 0.2970(14) 0.7261(8) 0.039(2) Uani 1 1 d . . . . .
C2 C 0.6232(18) 0.1613(12) 0.7125(8) 0.038(2) Uani 1 1 d . . . . .
C3 C 0.718(2) -0.0260(14) 0.7829(9) 0.049(3) Uani 1 1 d . . . . .
C4 C 0.568(2) -0.1225(15) 0.8821(11) 0.061(3) Uani 1 1 d . . . . .
C5 C -0.0150(19) 0.3798(15) 0.8602(10) 0.062(3) Uani 1 1 d . . . . .
H5A H -0.082975 0.330093 0.938173 0.092 Uiso 1 1 calc R U . . .
H5B H -0.139457 0.404278 0.805758 0.092 Uiso 1 1 calc R U . . .
H5C H 0.017416 0.494934 0.857349 0.092 Uiso 1 1 calc R U . . .


_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
Cu1 N1 1.933(8) . ?
Cu1 N1 1.933(8) 2_666 ?
Cu1 Br1 2.5240(11) . ?
Cu1 Br1 2.5240(11) 2_666 ?
Se1 N3 1.773(9) . ?
Se1 N2 1.805(7) . ?
O1 C1 1.332(11) . ?
O1 C5 1.451(11) . ?
N1 C1 1.261(11) . ?
N1 H1N 0.79(9) . ?
N2 C2 1.281(11) . ?
N3 C3 1.328(12) . ?
N4 C4 1.118(14) . ?
C1 C2 1.494(12) . ?
C2 C3 1.429(13) . ?
C3 C4 1.484(15) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 N1 180.0 . 2_666 ?
N1 Cu1 Br1 90.3(2) . . ?
N1 Cu1 Br1 89.7(2) 2_666 . ?
N1 Cu1 Br1 89.7(2) . 2_666 ?
N1 Cu1 Br1 90.3(2) 2_666 2_666 ?
Br1 Cu1 Br1 180.0 . 2_666 ?
N3 Se1 N2 92.7(3) . . ?
C1 O1 C5 117.0(8) . . ?
C1 N1 Cu1 123.8(6) . . ?
C1 N1 H1N 116(7) . . ?
Cu1 N1 H1N 120(7) . . ?
C2 N2 Se1 108.0(6) . . ?
C3 N3 Se1 106.4(6) . . ?
N1 C1 O1 128.9(9) . . ?
N1 C1 C2 118.7(8) . . ?
O1 C1 C2 112.3(8) . . ?
N2 C2 C3 115.7(8) . . ?
N2 C2 C1 117.8(8) . . ?
C3 C2 C1 126.4(9) . . ?
N3 C3 C2 117.1(9) . . ?
N3 C3 C4 116.8(9) . . ?
C2 C3 C4 126.1(10) . . ?
N4 C4 C3 176.8(13) . . ?
O1 C5 H5A 109.5 . . ?
O1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?

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
N3 Se1 N2 C2 0.7(7) . . . . ?
N2 Se1 N3 C3 1.1(7) . . . . ?
Cu1 N1 C1 O1 179.3(7) . . . . ?
Cu1 N1 C1 C2 -0.4(12) . . . . ?
C5 O1 C1 N1 -10.0(15) . . . . ?
C5 O1 C1 C2 169.7(8) . . . . ?
Se1 N2 C2 C3 -2.4(10) . . . . ?
Se1 N2 C2 C1 179.9(6) . . . . ?
N1 C1 C2 N2 11.6(13) . . . . ?
O1 C1 C2 N2 -168.1(8) . . . . ?
N1 C1 C2 C3 -165.8(9) . . . . ?
O1 C1 C2 C3 14.5(13) . . . . ?
Se1 N3 C3 C2 -2.7(11) . . . . ?
Se1 N3 C3 C4 177.4(8) . . . . ?
N2 C2 C3 N3 3.6(13) . . . . ?
C1 C2 C3 N3 -178.9(9) . . . . ?
N2 C2 C3 C4 -176.5(10) . . . . ?
C1 C2 C3 C4 1.0(16) . . . . ?

_refine_diff_density_max         0.735
_refine_diff_density_min         -0.645
_refine_diff_density_rms         0.146



