# 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_AO1
_database_code_depnum_ccdc_archive 'CCDC 2213810'
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_AO1                 
;                                                                                       
PROBLEM: Short Inter HL..A Contact Br1 ..Se1     .       3.25 Ang.
                                   2-x,1-y,1-z = 3_766 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-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H22 Br4 Cu2 N2 O2 Se2'
_chemical_formula_sum            'C24 H22 Br4 Cu2 N2 O2 Se2'
_chemical_formula_weight         975.07

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'
Cu Cu 0.3201 1.2651 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.1270(8)
_cell_length_b                   13.0444(15)
_cell_length_c                   14.4480(17)
_cell_angle_alpha                90
_cell_angle_beta                 99.666(4)
_cell_angle_gamma                90
_cell_volume                     1509.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4818
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      26.33

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.145
_exptl_crystal_F_000             924
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    9.136
_shelx_estimated_absorpt_T_min   0.184
_shelx_estimated_absorpt_T_max   0.383
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.132
_exptl_absorpt_correction_T_max  0.336
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(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            22506
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.117
_diffrn_reflns_theta_max         26.386
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3077
_reflns_number_gt                2446
_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    'SHELXT-2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0531P)²+2.4087P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3077
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.1001
_refine_ls_wR_factor_gt          0.0915
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.001
_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 0.56971(8) 0.39735(5) 0.54842(4) 0.02330(17) Uani 1 1 d . . . . .
Br1 Br 0.84857(7) 0.49521(5) 0.62212(4) 0.03039(16) Uani 1 1 d . . . . .
Br2 Br 0.61159(8) 0.24008(5) 0.47248(4) 0.03712(18) Uani 1 1 d . . . . .
Se1 Se 0.75819(6) 0.47926(4) 0.39112(4) 0.02190(14) Uani 1 1 d . . . . .
O1 O 0.5691(4) 0.4767(3) 0.4320(3) 0.0232(8) Uani 1 1 d . . . . .
N1 N 0.5277(6) 0.3341(4) 0.6664(3) 0.0254(10) Uani 1 1 d . . . . .
C1 C 0.6594(7) 0.3012(5) 0.7288(4) 0.0310(13) Uani 1 1 d . . . . .
H1 H 0.767627 0.303875 0.712187 0.037 Uiso 1 1 calc R U . . .
C2 C 0.6420(9) 0.2637(5) 0.8160(5) 0.0385(15) Uani 1 1 d . . . . .
H2 H 0.736358 0.239536 0.858246 0.046 Uiso 1 1 calc R U . . .
C3 C 0.4861(8) 0.2621(5) 0.8408(4) 0.0336(13) Uani 1 1 d . . . . .
H3 H 0.471641 0.238170 0.901034 0.040 Uiso 1 1 calc R U . . .
C4 C 0.3498(8) 0.2957(4) 0.7770(4) 0.0298(12) Uani 1 1 d . . . . .
H4 H 0.240944 0.294351 0.792665 0.036 Uiso 1 1 calc R U . . .
C5 C 0.3748(7) 0.3314(4) 0.6898(4) 0.0245(11) Uani 1 1 d . . . . .
C6 C 0.6773(7) 0.4496(4) 0.2593(4) 0.0260(11) Uani 1 1 d . . . . .
C7 C 0.5106(8) 0.4253(5) 0.2330(5) 0.0397(15) Uani 1 1 d . . . . .
H7 H 0.437032 0.425739 0.277596 0.048 Uiso 1 1 calc R U . . .
C8 C 0.4532(10) 0.4001(6) 0.1395(5) 0.0505(19) Uani 1 1 d . . . . .
H8 H 0.339155 0.383061 0.119236 0.061 Uiso 1 1 calc R U . . .
C9 C 0.5637(11) 0.4002(5) 0.0766(5) 0.0513(19) Uani 1 1 d . . . . .
H9 H 0.524254 0.383836 0.012630 0.062 Uiso 1 1 calc R U . . .
C10 C 0.7297(10) 0.4234(6) 0.1046(4) 0.0460(17) Uani 1 1 d . . . . .
H10 H 0.803734 0.422213 0.060261 0.055 Uiso 1 1 calc R U . . .
C11 C 0.7894(9) 0.4484(5) 0.1976(4) 0.0377(14) Uani 1 1 d . . . . .
H11 H 0.903814 0.464275 0.217936 0.045 Uiso 1 1 calc R U . . .
C12 C 0.2325(6) 0.3700(4) 0.6199(4) 0.0248(11) Uani 1 1 d . . . . .
H12A H 0.126051 0.349917 0.639545 0.030 Uiso 1 1 calc R U . . .
H12B H 0.236332 0.338433 0.558015 0.030 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 1.974(4) . ?
Cu1 O1 1.974(4) . ?
Cu1 O1 2.039(4) 3_666 ?
Cu1 Br2 2.3777(9) . ?
Cu1 Br1 2.6625(9) . ?
Se1 O1 1.737(3) . ?
Se1 C6 1.947(5) . ?
Se1 C12 1.975(5) 3_666 ?
N1 C5 1.342(7) . ?
N1 C1 1.348(7) . ?
C1 C2 1.381(8) . ?
C1 H1 0.9500 . ?
C2 C3 1.374(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(7) . ?
C4 H4 0.9500 . ?
C5 C12 1.489(8) . ?
C6 C11 1.378(8) . ?
C6 C7 1.381(8) . ?
C7 C8 1.392(9) . ?
C7 H7 0.9500 . ?
C8 C9 1.381(11) . ?
C8 H8 0.9500 . ?
C9 C10 1.376(10) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(9) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?

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 O1 168.12(17) . . ?
N1 Cu1 O1 92.14(17) . 3_666 ?
O1 Cu1 O1 76.90(16) . 3_666 ?
N1 Cu1 Br2 95.53(14) . . ?
O1 Cu1 Br2 92.26(11) . . ?
O1 Cu1 Br2 152.18(11) 3_666 . ?
N1 Cu1 Br1 96.56(14) . . ?
O1 Cu1 Br1 88.25(11) . . ?
O1 Cu1 Br1 90.69(11) 3_666 . ?
Br2 Cu1 Br1 114.83(3) . . ?
O1 Se1 C6 99.0(2) . . ?
O1 Se1 C12 95.42(19) . 3_666 ?
C6 Se1 C12 97.5(2) . 3_666 ?
Se1 O1 Cu1 115.09(18) . . ?
Se1 O1 Cu1 125.0(2) . 3_666 ?
Cu1 O1 Cu1 103.10(16) . 3_666 ?
C5 N1 C1 119.2(5) . . ?
C5 N1 Cu1 122.0(4) . . ?
C1 N1 Cu1 118.5(4) . . ?
N1 C1 C2 122.1(5) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C3 C2 C1 118.9(6) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 119.3(6) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 119.1(5) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 121.3(5) . . ?
N1 C5 C12 117.8(5) . . ?
C4 C5 C12 120.8(5) . . ?
C11 C6 C7 123.0(6) . . ?
C11 C6 Se1 119.0(4) . . ?
C7 C6 Se1 118.0(4) . . ?
C6 C7 C8 118.3(6) . . ?
C6 C7 H7 120.8 . . ?
C8 C7 H7 120.8 . . ?
C9 C8 C7 119.3(7) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C10 C9 C8 121.4(6) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C11 120.2(6) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C6 C11 C10 117.9(6) . . ?
C6 C11 H11 121.1 . . ?
C10 C11 H11 121.1 . . ?
C5 C12 Se1 110.8(4) . 3_666 ?
C5 C12 H12A 109.5 . . ?
Se1 C12 H12A 109.5 3_666 . ?
C5 C12 H12B 109.5 . . ?
Se1 C12 H12B 109.5 3_666 . ?
H12A C12 H12B 108.1 . . ?

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 Se1 O1 Cu1 133.4(2) . . . . ?
C12 Se1 O1 Cu1 -128.1(2) 3_666 . . . ?
C6 Se1 O1 Cu1 -97.3(3) . . . 3_666 ?
C12 Se1 O1 Cu1 1.2(3) 3_666 . . 3_666 ?
C5 N1 C1 C2 0.7(9) . . . . ?
Cu1 N1 C1 C2 174.6(5) . . . . ?
N1 C1 C2 C3 -1.5(10) . . . . ?
C1 C2 C3 C4 1.5(9) . . . . ?
C2 C3 C4 C5 -0.7(9) . . . . ?
C1 N1 C5 C4 0.1(8) . . . . ?
Cu1 N1 C5 C4 -173.6(4) . . . . ?
C1 N1 C5 C12 178.9(5) . . . . ?
Cu1 N1 C5 C12 5.2(7) . . . . ?
C3 C4 C5 N1 -0.1(8) . . . . ?
C3 C4 C5 C12 -178.8(5) . . . . ?
C11 C6 C7 C8 -1.0(10) . . . . ?
Se1 C6 C7 C8 -177.6(5) . . . . ?
C6 C7 C8 C9 0.0(10) . . . . ?
C7 C8 C9 C10 0.8(11) . . . . ?
C8 C9 C10 C11 -0.7(11) . . . . ?
C7 C6 C11 C10 1.2(10) . . . . ?
Se1 C6 C11 C10 177.7(5) . . . . ?
C9 C10 C11 C6 -0.3(10) . . . . ?
N1 C5 C12 Se1 -71.5(5) . . . 3_666 ?
C4 C5 C12 Se1 107.2(5) . . . 3_666 ?

_refine_diff_density_max         1.062
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.171



