# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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 1942943'
loop_
_audit_author_name
_audit_author_address
'Ricardo Baggio'
;CNEA
Argentina
;
#Added by publCIF



_audit_update_record             
;
2019-07-24 deposited with the CCDC.	2020-03-13 downloaded from the CCDC.
;
# publcif _publ_body_element loop end

# SQUEEZE RESULTS (Version = 260918)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.001 -0.046 0.000 759 337 ' '
2 0.853 -0.034 0.500 758 337 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?



_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H32 Cu2 N8 O4'
_chemical_formula_sum            'C42 H32 Cu2 N8 O4'
_chemical_formula_weight         839.83

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   24.5552(17)
_cell_length_b                   9.9210(6)
_cell_length_c                   19.9673(12)
_cell_angle_alpha                90
_cell_angle_beta                 102.042(2)
_cell_angle_gamma                90
_cell_volume                     4757.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1228
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      25.12

_exptl_crystal_description       fragment
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.173
_exptl_crystal_F_000             1720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.937
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_T_max  0.90
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, Oxford Diffraction (2009) '
_diffrn_ambient_temperature      295(2)

_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Gemini CCD S Ultra'
_diffrn_measurement_method       'ω scans, thick slices'

_diffrn_reflns_number            31822
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.221
_diffrn_reflns_theta_max         25.715
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4523
_reflns_number_gt                3905
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'CrysAlisPro (Oxford Diffraction, 2009)'
_computing_cell_refinement       'CrysAlisPro '
_computing_data_reduction        'CrysAlisPro '
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'SHELXTL   (Sheldrick, 2008)'
_computing_publication_material  'SHELXL-2018/1, PLATON (Spek, 2003)'



_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0426P)²+7.6557P] where P=(Fo²+2Fc²)/3'
_atom_site_solution_primary      'Direct method'
_atom_site_solution_secondary    'Fourier Difference Synthesis'


_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4523
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_ref         0.0788
_refine_ls_wR_factor_gt          0.0750
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

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 0.50878(2) 0.88372(2) -0.17097(2) 0.01569(8) Uani 1 1 d . . . . .
N1A N 0.46134(7) 0.71685(16) -0.17854(8) 0.0198(3) Uani 1 1 d . . . . .
N2A N 0.57053(7) 0.74655(16) -0.14743(8) 0.0216(3) Uani 1 1 d . . . . .
C1A C 0.40623(9) 0.7061(2) -0.19325(10) 0.0276(5) Uani 1 1 d . . . . .
H1A H 0.384819 0.784231 -0.199411 0.033 Uiso 1 1 calc R U . . .
C2A C 0.37938(11) 0.5810(3) -0.19976(13) 0.0397(6) Uani 1 1 d . . . . .
H2A H 0.340705 0.576448 -0.209981 0.048 Uiso 1 1 calc R U . . .
C3A C 0.41018(12) 0.4661(2) -0.19104(13) 0.0424(6) Uani 1 1 d . . . . .
H3A H 0.392542 0.382692 -0.196328 0.051 Uiso 1 1 calc R U . . .
C4A C 0.46818(10) 0.4729(2) -0.17419(11) 0.0309(5) Uani 1 1 d . . . . .
C5A C 0.50479(13) 0.3582(2) -0.16179(11) 0.0400(6) Uani 1 1 d . . . . .
H5A H 0.489803 0.271751 -0.166390 0.048 Uiso 1 1 calc R U . . .
C6A C 0.56032(13) 0.3740(2) -0.14366(12) 0.0408(6) Uani 1 1 d . . . . .
H6A H 0.582865 0.298034 -0.134865 0.049 Uiso 1 1 calc R U . . .
C7A C 0.58578(10) 0.5051(2) -0.13751(11) 0.0338(5) Uani 1 1 d . . . . .
C8A C 0.64322(11) 0.5290(3) -0.11912(13) 0.0460(7) Uani 1 1 d . . . . .
H8A H 0.667926 0.457186 -0.109303 0.055 Uiso 1 1 calc R U . . .
C9A C 0.66288(11) 0.6589(3) -0.11566(13) 0.0441(6) Uani 1 1 d . . . . .
H9A H 0.700951 0.675616 -0.103866 0.053 Uiso 1 1 calc R U . . .
C10A C 0.62529(9) 0.7657(2) -0.12997(11) 0.0305(5) Uani 1 1 d . . . . .
H10A H 0.638993 0.853357 -0.127219 0.037 Uiso 1 1 calc R U . . .
C11A C 0.55099(9) 0.61772(19) -0.15085(10) 0.0239(4) Uani 1 1 d . . . . .
C12A C 0.49201(9) 0.60209(19) -0.16836(9) 0.0231(4) Uani 1 1 d . . . . .
O1B O 0.43673(6) 1.02001(13) -0.31854(6) 0.0211(3) Uani 1 1 d . . . . .
O2B O 0.44318(5) 0.99357(14) -0.20567(7) 0.0220(3) Uani 1 1 d . . . . .
N1B N 0.22360(8) 1.3476(2) -0.27734(12) 0.0413(5) Uani 1 1 d . . . . .
H1BA H 0.208904 1.381857 -0.318910 0.073(11) Uiso 1 1 d R . . . .
H1BB H 0.225624 1.381957 -0.235180 0.050(9) Uiso 1 1 d R . . . .
C1B C 0.41891(8) 1.03634(17) -0.26386(9) 0.0166(4) Uani 1 1 d . . . . .
C2B C 0.36575(8) 1.10970(18) -0.26817(10) 0.0186(4) Uani 1 1 d . . . . .
C3B C 0.34760(8) 1.14406(19) -0.20862(10) 0.0210(4) Uani 1 1 d . . . . .
H3B H 0.367674 1.115067 -0.166337 0.025 Uiso 1 1 calc R U . . .
C4B C 0.30036(8) 1.2203(2) -0.21181(11) 0.0258(4) Uani 1 1 d . . . . .
H4B H 0.288687 1.241816 -0.171710 0.031 Uiso 1 1 calc R U . . .
C5B C 0.26978(8) 1.2656(2) -0.27462(12) 0.0279(5) Uani 1 1 d . . . . .
C6B C 0.28559(9) 1.2235(2) -0.33462(11) 0.0303(5) Uani 1 1 d . . . . .
H6B H 0.264038 1.247003 -0.377046 0.036 Uiso 1 1 calc R U . . .
C7B C 0.33283(8) 1.1476(2) -0.33106(11) 0.0257(4) Uani 1 1 d . . . . .
H7B H 0.343109 1.120889 -0.371330 0.031 Uiso 1 1 calc R U . . .
N1C N 0.50397(7) 0.95493(16) -0.06504(8) 0.0194(3) Uani 1 1 d . . . . .
C1C C 0.54742(9) 1.0056(2) -0.02146(10) 0.0271(5) Uani 1 1 d . . . . .
H1C H 0.581448 1.011853 -0.034747 0.033 Uiso 1 1 calc R U . . .
C2C C 0.45643(9) 0.9505(2) -0.04320(10) 0.0289(5) Uani 1 1 d . . . . .
H2C H 0.424756 0.916886 -0.072276 0.035 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 O1B 1.9442(13) 2_654 ?
Cu1 O2B 1.9486(13) . ?
Cu1 N1A 2.0117(16) . ?
Cu1 N2A 2.0186(16) . ?
Cu1 N1C 2.2563(15) . ?
N1A C1A 1.328(3) . ?
N1A C12A 1.357(3) . ?
N2A C10A 1.331(3) . ?
N2A C11A 1.362(3) . ?
C1A C2A 1.399(3) . ?
C1A H1A 0.9300 . ?
C2A C3A 1.359(4) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.395(4) . ?
C3A H3A 0.9300 . ?
C4A C12A 1.403(3) . ?
C4A C5A 1.440(3) . ?
C5A C6A 1.345(4) . ?
C5A H5A 0.9300 . ?
C6A C7A 1.437(3) . ?
C6A H6A 0.9300 . ?
C7A C8A 1.402(4) . ?
C7A C11A 1.398(3) . ?
C8A C9A 1.373(4) . ?
C8A H8A 0.9300 . ?
C9A C10A 1.395(3) . ?
C9A H9A 0.9300 . ?
C10A H10A 0.9300 . ?
C11A C12A 1.426(3) . ?
O1B C1B 1.269(2) . ?
O2B C1B 1.263(2) . ?
N1B C5B 1.387(3) . ?
N1B H1BA 0.9000 . ?
N1B H1BB 0.9001 . ?
C1B C2B 1.481(3) . ?
C2B C7B 1.396(3) . ?
C2B C3B 1.396(3) . ?
C3B C4B 1.375(3) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.395(3) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.398(3) . ?
C6B C7B 1.373(3) . ?
C6B H6B 0.9300 . ?
C7B H7B 0.9300 . ?
N1C C2C 1.329(3) . ?
N1C C1C 1.327(3) . ?
C1C C2C 1.384(3) 5_675 ?
C1C H1C 0.9300 . ?
C2C H2C 0.9300 . ?

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
O1B Cu1 O2B 96.27(6) 2_654 . ?
O1B Cu1 N1A 164.80(6) 2_654 . ?
O2B Cu1 N1A 90.62(6) . . ?
O1B Cu1 N2A 89.63(6) 2_654 . ?
O2B Cu1 N2A 170.05(6) . . ?
N1A Cu1 N2A 81.82(7) . . ?
O1B Cu1 N1C 93.15(6) 2_654 . ?
O2B Cu1 N1C 87.55(6) . . ?
N1A Cu1 N1C 100.69(6) . . ?
N2A Cu1 N1C 100.16(6) . . ?
C1A N1A C12A 118.31(17) . . ?
C1A N1A Cu1 129.04(14) . . ?
C12A N1A Cu1 112.63(13) . . ?
C10A N2A C11A 118.25(18) . . ?
C10A N2A Cu1 129.34(15) . . ?
C11A N2A Cu1 112.42(13) . . ?
N1A C1A C2A 122.0(2) . . ?
N1A C1A H1A 119.0 . . ?
C2A C1A H1A 119.0 . . ?
C3A C2A C1A 119.6(2) . . ?
C3A C2A H2A 120.2 . . ?
C1A C2A H2A 120.2 . . ?
C2A C3A C4A 120.2(2) . . ?
C2A C3A H3A 119.9 . . ?
C4A C3A H3A 119.9 . . ?
C3A C4A C12A 116.8(2) . . ?
C3A C4A C5A 124.9(2) . . ?
C12A C4A C5A 118.2(2) . . ?
C6A C5A C4A 121.0(2) . . ?
C6A C5A H5A 119.5 . . ?
C4A C5A H5A 119.5 . . ?
C5A C6A C7A 121.8(2) . . ?
C5A C6A H6A 119.1 . . ?
C7A C6A H6A 119.1 . . ?
C8A C7A C11A 117.1(2) . . ?
C8A C7A C6A 124.9(2) . . ?
C11A C7A C6A 118.0(2) . . ?
C9A C8A C7A 119.8(2) . . ?
C9A C8A H8A 120.1 . . ?
C7A C8A H8A 120.1 . . ?
C8A C9A C10A 119.5(2) . . ?
C8A C9A H9A 120.3 . . ?
C10A C9A H9A 120.3 . . ?
N2A C10A C9A 122.3(2) . . ?
N2A C10A H10A 118.8 . . ?
C9A C10A H10A 118.8 . . ?
N2A C11A C7A 123.1(2) . . ?
N2A C11A C12A 116.33(17) . . ?
C7A C11A C12A 120.59(19) . . ?
N1A C12A C4A 123.0(2) . . ?
N1A C12A C11A 116.69(17) . . ?
C4A C12A C11A 120.29(19) . . ?
C1B O1B Cu1 123.39(12) . 2_654 ?
C1B O2B Cu1 135.32(12) . . ?
C5B N1B H1BA 115.1 . . ?
C5B N1B H1BB 107.5 . . ?
H1BA N1B H1BB 130.7 . . ?
O2B C1B O1B 124.58(17) . . ?
O2B C1B C2B 117.34(16) . . ?
O1B C1B C2B 118.09(16) . . ?
C7B C2B C3B 118.20(18) . . ?
C7B C2B C1B 121.50(17) . . ?
C3B C2B C1B 120.30(17) . . ?
C4B C3B C2B 120.72(19) . . ?
C4B C3B H3B 119.6 . . ?
C2B C3B H3B 119.6 . . ?
C3B C4B C5B 120.65(19) . . ?
C3B C4B H4B 119.7 . . ?
C5B C4B H4B 119.7 . . ?
N1B C5B C4B 120.4(2) . . ?
N1B C5B C6B 120.8(2) . . ?
C4B C5B C6B 118.70(19) . . ?
C7B C6B C5B 120.17(19) . . ?
C7B C6B H6B 119.9 . . ?
C5B C6B H6B 119.9 . . ?
C6B C7B C2B 121.26(19) . . ?
C6B C7B H7B 119.4 . . ?
C2B C7B H7B 119.4 . . ?
C2C N1C C1C 115.99(17) . . ?
C2C N1C Cu1 121.23(13) . . ?
C1C N1C Cu1 122.77(13) . . ?
N1C C1C C2C 121.92(18) . 5_675 ?
N1C C1C H1C 119.0 . . ?
C2C C1C H1C 119.0 5_675 . ?
N1C C2C C1C 122.08(19) . 5_675 ?
N1C C2C H2C 119.0 . . ?
C1C C2C H2C 119.0 5_675 . ?

_refine_diff_density_max         0.284
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.051



loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



_publcif_funding_html            
;
;
