# 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_AO3B_A
_database_code_depnum_ccdc_archive 'CCDC 2213808'
loop_
_audit_author_name
_audit_author_address
'Atash Gurbanov'
;Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2022-10-18 deposited with the CCDC.	2023-04-21 downloaded from the CCDC.
;

_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 Cl4 Cu2 N2 O2 Se2'
_chemical_formula_sum            'C24 H22 Cl4 Cu2 N2 O2 Se2'
_chemical_formula_weight         797.23

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'
O O 0.0106 0.0060 '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'
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'

_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                   7.7872(2)
_cell_length_b                   13.1414(4)
_cell_length_c                   14.2735(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.9450(10)
_cell_angle_gamma                90
_cell_volume                     1434.10(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7501
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      26.37

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.846
_exptl_crystal_F_000             780
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    4.419
_shelx_estimated_absorpt_T_min   0.443
_shelx_estimated_absorpt_T_max   0.457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.425
_exptl_absorpt_correction_T_max  0.432
_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            21647
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.782
_diffrn_reflns_theta_max         26.374
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2903
_reflns_number_gt                2529
_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)+(0.0148P)²+0.8313P] 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         2903
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0252
_refine_ls_R_factor_gt           0.0184
_refine_ls_wR_factor_ref         0.0411
_refine_ls_wR_factor_gt          0.0391
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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 0.42516(3) 0.39810(2) 0.45215(2) 0.01620(7) Uani 1 1 d . . . . .
Cl1 Cl 0.15286(6) 0.49358(4) 0.37640(4) 0.02321(12) Uani 1 1 d . . . . .
Cl2 Cl 0.36237(8) 0.25567(4) 0.52431(4) 0.02931(13) Uani 1 1 d . . . . .
Se1 Se 0.76988(3) 0.51628(2) 0.39276(2) 0.01491(6) Uani 1 1 d . . . . .
O1 O 0.42859(17) 0.48004(11) 0.56899(10) 0.0173(3) Uani 1 1 d . . . . .
N1 N 0.4673(2) 0.33193(13) 0.33450(12) 0.0179(4) Uani 1 1 d . . . . .
C1 C 0.6271(3) 0.32748(15) 0.31098(14) 0.0167(4) Uani 1 1 d . . . . .
C2 C 0.3281(3) 0.29779(17) 0.27150(16) 0.0243(5) Uani 1 1 d . . . . .
H2 H 0.215881 0.300460 0.288343 0.029 Uiso 1 1 calc R U . . .
C3 C 0.3423(3) 0.25906(18) 0.18335(16) 0.0275(5) Uani 1 1 d . . . . .
H3 H 0.242203 0.234703 0.140573 0.033 Uiso 1 1 calc R U . . .
C4 C 0.5056(3) 0.25657(16) 0.15885(15) 0.0254(5) Uani 1 1 d . . . . .
H4 H 0.518933 0.230965 0.098406 0.031 Uiso 1 1 calc R U . . .
C5 C 0.6493(3) 0.29157(16) 0.22283(15) 0.0215(4) Uani 1 1 d . . . . .
H5 H 0.762046 0.291004 0.206521 0.026 Uiso 1 1 calc R U . . .
C6 C 0.7781(3) 0.36634(16) 0.38238(15) 0.0191(4) Uani 1 1 d . . . . .
H6B H 0.888760 0.345958 0.363139 0.023 Uiso 1 1 calc R U . . .
H6A H 0.775646 0.335560 0.445421 0.023 Uiso 1 1 calc R U . . .
C7 C 0.6837(3) 0.54666(15) 0.25923(14) 0.0184(4) Uani 1 1 d . . . . .
C8 C 0.8005(3) 0.54870(18) 0.19642(16) 0.0269(5) Uani 1 1 d . . . . .
H8 H 0.920460 0.532473 0.217592 0.032 Uiso 1 1 calc R U . . .
C9 C 0.7364(4) 0.5752(2) 0.10155(16) 0.0369(6) Uani 1 1 d . . . . .
H9 H 0.812874 0.576745 0.057033 0.044 Uiso 1 1 calc R U . . .
C10 C 0.5623(4) 0.5993(2) 0.07248(17) 0.0398(7) Uani 1 1 d . . . . .
H10 H 0.519660 0.617339 0.007811 0.048 Uiso 1 1 calc R U . . .
C11 C 0.4488(4) 0.5974(2) 0.13599(18) 0.0371(6) Uani 1 1 d . . . . .
H11 H 0.329208 0.614600 0.114864 0.045 Uiso 1 1 calc R U . . .
C12 C 0.5093(3) 0.57050(17) 0.23105(17) 0.0272(5) Uani 1 1 d . . . . .
H12 H 0.432148 0.568641 0.275216 0.033 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 1.9730(17) . ?
Cu1 O1 1.9811(14) . ?
Cu1 O1 2.0206(14) 3_666 ?
Cu1 Cl2 2.2349(6) . ?
Cu1 Cl1 2.5237(6) . ?
Se1 O1 1.7347(13) 3_666 ?
Se1 C7 1.938(2) . ?
Se1 C6 1.978(2) . ?
N1 C2 1.347(3) . ?
N1 C1 1.350(3) . ?
C1 C5 1.385(3) . ?
C1 C6 1.492(3) . ?
C2 C3 1.381(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.381(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 H6B 0.9900 . ?
C6 H6A 0.9900 . ?
C7 C12 1.378(3) . ?
C7 C8 1.393(3) . ?
C8 C9 1.396(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.377(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.381(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.395(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?

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 168.02(6) . . ?
N1 Cu1 O1 91.88(6) . 3_666 ?
O1 Cu1 O1 77.12(6) . 3_666 ?
N1 Cu1 Cl2 96.28(5) . . ?
O1 Cu1 Cl2 92.08(4) . . ?
O1 Cu1 Cl2 155.70(4) 3_666 . ?
N1 Cu1 Cl1 96.69(5) . . ?
O1 Cu1 Cl1 88.07(4) . . ?
O1 Cu1 Cl1 89.63(4) 3_666 . ?
Cl2 Cu1 Cl1 111.98(2) . . ?
O1 Se1 C7 98.10(8) 3_666 . ?
O1 Se1 C6 95.43(8) 3_666 . ?
C7 Se1 C6 98.14(8) . . ?
Se1 O1 Cu1 114.19(7) 3_666 . ?
Se1 O1 Cu1 125.87(8) 3_666 3_666 ?
Cu1 O1 Cu1 102.88(6) . 3_666 ?
C2 N1 C1 118.84(18) . . ?
C2 N1 Cu1 118.18(14) . . ?
C1 N1 Cu1 122.72(14) . . ?
N1 C1 C5 121.36(19) . . ?
N1 C1 C6 117.33(17) . . ?
C5 C1 C6 121.27(19) . . ?
N1 C2 C3 122.5(2) . . ?
N1 C2 H2 118.7 . . ?
C3 C2 H2 118.7 . . ?
C2 C3 C4 118.4(2) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C3 C4 C5 119.6(2) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C1 119.2(2) . . ?
C4 C5 H5 120.4 . . ?
C1 C5 H5 120.4 . . ?
C1 C6 Se1 111.08(14) . . ?
C1 C6 H6B 109.4 . . ?
Se1 C6 H6B 109.4 . . ?
C1 C6 H6A 109.4 . . ?
Se1 C6 H6A 109.4 . . ?
H6B C6 H6A 108.0 . . ?
C12 C7 C8 122.4(2) . . ?
C12 C7 Se1 118.16(16) . . ?
C8 C7 Se1 119.37(16) . . ?
C7 C8 C9 118.2(2) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 H8 120.9 . . ?
C10 C9 C8 120.0(2) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 121.0(2) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C10 C11 C12 120.2(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C7 C12 C11 118.3(2) . . ?
C7 C12 H12 120.9 . . ?
C11 C12 H12 120.9 . . ?

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
C2 N1 C1 C5 1.9(3) . . . . ?
Cu1 N1 C1 C5 -172.12(15) . . . . ?
C2 N1 C1 C6 179.77(18) . . . . ?
Cu1 N1 C1 C6 5.7(2) . . . . ?
C1 N1 C2 C3 -0.5(3) . . . . ?
Cu1 N1 C2 C3 173.85(18) . . . . ?
N1 C2 C3 C4 -0.8(3) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C3 C4 C5 C1 0.7(3) . . . . ?
N1 C1 C5 C4 -2.1(3) . . . . ?
C6 C1 C5 C4 -179.82(19) . . . . ?
N1 C1 C6 Se1 -70.9(2) . . . . ?
C5 C1 C6 Se1 106.92(19) . . . . ?
C12 C7 C8 C9 -0.5(3) . . . . ?
Se1 C7 C8 C9 -177.17(18) . . . . ?
C7 C8 C9 C10 0.5(4) . . . . ?
C8 C9 C10 C11 -0.1(4) . . . . ?
C9 C10 C11 C12 -0.4(4) . . . . ?
C8 C7 C12 C11 0.1(3) . . . . ?
Se1 C7 C12 C11 176.79(18) . . . . ?
C10 C11 C12 C7 0.4(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C12 H12 O1 0.95 2.37 2.880(3) 113.3 3_666 yes

_refine_diff_density_max         0.323
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.062

