# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_2
_database_code_depnum_ccdc_archive 'CCDC 2168446'
_audit_update_record             
;
2022-04-23 deposited with the CCDC.	2023-04-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H34 Cu2 I2 N4 O2'
_chemical_formula_weight         647.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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                   7.2810(4)
_cell_length_b                   14.5330(7)
_cell_length_c                   11.0519(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.619(5)
_cell_angle_gamma                90.00
_cell_volume                     1136.56(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1792
_cell_measurement_theta_min      4.1090
_cell_measurement_theta_max      72.0000

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.891
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             628
_exptl_absorpt_coefficient_mu    23.710
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.18994
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3736
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         5.12
_diffrn_reflns_theta_max         72.11
_reflns_number_total             2170
_reflns_number_gt                1975
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0671P)²+0.0890P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2170
_refine_ls_number_parameters     104
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1120
_refine_ls_wR_factor_gt          0.1069
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.82515(5) 0.13594(3) 0.70400(3) 0.03575(16) Uani 1 1 d . . .
Cu1 Cu 0.62114(11) 0.05447(6) 0.10310(6) 0.0281(2) Uani 1 1 d . . .
N1 N 0.6635(6) 0.0624(4) 0.2900(4) 0.0320(10) Uani 1 1 d . . .
O1 O 0.4268(7) -0.0352(4) 0.0732(3) 0.0551(15) Uani 1 1 d . . .
H1D H 0.3688 -0.0631 0.1302 0.066 Uiso 1 1 calc R . .
N2 N 0.8139(7) 0.1551(4) 0.1167(4) 0.0348(11) Uani 1 1 d . . .
C2 C 0.6990(9) -0.0267(5) 0.3536(6) 0.0456(15) Uani 1 1 d . . .
H2A H 0.5883 -0.0646 0.3299 0.068 Uiso 1 1 calc R . .
H2B H 0.7287 -0.0173 0.4421 0.068 Uiso 1 1 calc R . .
H2C H 0.8032 -0.0566 0.3305 0.068 Uiso 1 1 calc R . .
C6 C 0.7481(11) 0.2345(5) 0.0331(6) 0.0482(16) Uani 1 1 d . . .
H6A H 0.7394 0.2166 -0.0516 0.072 Uiso 1 1 calc R . .
H6B H 0.8362 0.2843 0.0547 0.072 Uiso 1 1 calc R . .
H6C H 0.6261 0.2539 0.0423 0.072 Uiso 1 1 calc R . .
C1 C 0.4979(11) 0.1042(5) 0.3237(6) 0.0483(16) Uani 1 1 d . . .
H1A H 0.5276 0.1173 0.4113 0.072 Uiso 1 1 calc R . .
H1B H 0.3932 0.0623 0.3039 0.072 Uiso 1 1 calc R . .
H1C H 0.4651 0.1603 0.2779 0.072 Uiso 1 1 calc R . .
C5 C 0.9877(9) 0.1177(5) 0.0859(7) 0.0462(15) Uani 1 1 d . . .
H5A H 1.0321 0.0657 0.1383 0.069 Uiso 1 1 calc R . .
H5B H 1.0836 0.1644 0.0994 0.069 Uiso 1 1 calc R . .
H5C H 0.9595 0.0988 0.0003 0.069 Uiso 1 1 calc R . .
C3 C 0.8420(12) 0.1167(7) 0.3331(6) 0.061(2) Uani 1 1 d . . .
H3A H 0.8478 0.1415 0.4154 0.073 Uiso 1 1 calc R . .
H3B H 0.9504 0.0768 0.3382 0.073 Uiso 1 1 calc R . .
C4 C 0.8477(13) 0.1910(6) 0.2473(6) 0.058(2) Uani 1 1 d . . .
H4A H 0.9700 0.2210 0.2697 0.069 Uiso 1 1 calc R . .
H4B H 0.7518 0.2362 0.2524 0.069 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.0420(2) 0.0420(3) 0.0283(2) -0.00320(12) 0.01833(15) -0.00590(13)
Cu1 0.0358(4) 0.0360(5) 0.0136(3) -0.0061(3) 0.0080(3) -0.0167(3)
N1 0.037(2) 0.044(3) 0.0159(18) -0.0034(16) 0.0089(17) -0.0131(19)
O1 0.075(3) 0.078(3) 0.0155(17) -0.0132(19) 0.0163(19) -0.054(3)
N2 0.046(3) 0.040(3) 0.020(2) -0.0051(18) 0.0108(18) -0.022(2)
C2 0.041(3) 0.060(4) 0.037(3) 0.016(3) 0.010(2) 0.009(3)
C6 0.075(5) 0.032(3) 0.043(3) -0.003(3) 0.025(3) -0.007(3)
C1 0.068(4) 0.047(4) 0.036(3) -0.003(3) 0.024(3) 0.008(3)
C5 0.040(3) 0.051(4) 0.045(3) 0.005(3) 0.006(3) -0.009(3)
C3 0.070(5) 0.089(6) 0.021(3) -0.008(3) 0.006(3) -0.046(5)
C4 0.087(5) 0.064(5) 0.023(3) -0.014(3) 0.016(3) -0.048(4)

_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 O1 1.895(4) . ?
Cu1 O1 1.918(4) 3_655 ?
Cu1 N2 2.008(5) . ?
Cu1 N1 2.019(4) . ?
Cu1 Cu1 2.9863(13) 3_655 ?
N1 C2 1.467(8) . ?
N1 C1 1.474(8) . ?
N1 C3 1.499(8) . ?
O1 Cu1 1.918(4) 3_655 ?
N2 C6 1.486(9) . ?
N2 C5 1.488(9) . ?
N2 C4 1.500(7) . ?
C3 C4 1.444(11) . ?

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
O1 Cu1 O1 76.86(18) . 3_655 ?
O1 Cu1 N2 173.8(2) . . ?
O1 Cu1 N2 97.99(17) 3_655 . ?
O1 Cu1 N1 98.35(17) . . ?
O1 Cu1 N1 174.6(2) 3_655 . ?
N2 Cu1 N1 86.93(19) . . ?
O1 Cu1 Cu1 38.71(11) . 3_655 ?
O1 Cu1 Cu1 38.16(12) 3_655 3_655 ?
N2 Cu1 Cu1 136.06(13) . 3_655 ?
N1 Cu1 Cu1 137.00(14) . 3_655 ?
C2 N1 C1 107.8(5) . . ?
C2 N1 C3 105.7(5) . . ?
C1 N1 C3 113.7(6) . . ?
C2 N1 Cu1 114.0(4) . . ?
C1 N1 Cu1 110.2(4) . . ?
C3 N1 Cu1 105.5(3) . . ?
Cu1 O1 Cu1 103.14(18) . 3_655 ?
C6 N2 C5 108.0(5) . . ?
C6 N2 C4 106.5(6) . . ?
C5 N2 C4 113.0(6) . . ?
C6 N2 Cu1 113.7(4) . . ?
C5 N2 Cu1 109.5(4) . . ?
C4 N2 Cu1 106.2(3) . . ?
C4 C3 N1 110.0(6) . . ?
C3 C4 N2 110.3(6) . . ?

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        72.11
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         1.220
_refine_diff_density_min         -1.190
_refine_diff_density_rms         0.172
