# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1590515'
_audit_update_record             
;
2017-12-11 deposited with the CCDC.
2019-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H24 Cu N8 O8'
_chemical_formula_weight         904.29

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'
N N 0.0311 0.0180 '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'

_space_group_crystal_system      tetragonal
_space_group_IT_number           86
_space_group_name_H-M_alt        'P 42/n'
_space_group_name_Hall           '-P 4bc'

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

_cell_length_a                   23.6145(7)
_cell_length_b                   23.6145(7)
_cell_length_c                   6.5579(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3657.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.01(10)
_cell_measurement_reflns_used    2051
_cell_measurement_theta_min      5.3060
_cell_measurement_theta_max      74.5180

_exptl_crystal_description       Prism
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    0.821
_exptl_crystal_F_000             922
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.745
_shelx_estimated_absorpt_T_min   0.807
_shelx_estimated_absorpt_T_max   0.896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.66148
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.01(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3503
_diffrn_reflns_number            6850
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         3.744
_diffrn_reflns_theta_max         74.332
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3597
_reflns_number_gt                2659
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0893P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00069(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3597
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1445
_refine_ls_wR_factor_gt          0.1373
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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 0.2500 0.2500 0.2500 0.03947(18) Uani 1 4 d S T P . .
O2 O 0.08139(8) 0.34208(7) 1.0066(3) 0.0673(5) Uani 1 1 d . . . . .
O1 O 0.10918(8) 0.47229(7) 0.5052(3) 0.0783(6) Uani 1 1 d . . . . .
C1 C -0.04553(10) 0.50137(9) 1.2313(3) 0.0566(6) Uani 1 1 d . . . . .
C2 C -0.03380(12) 0.44892(11) 1.3133(4) 0.0708(8) Uani 1 1 d . . . . .
H2 H -0.0513 0.4379 1.4340 0.085 Uiso 1 1 calc R U . . .
C3 C 0.00397(12) 0.41208(11) 1.2179(4) 0.0683(7) Uani 1 1 d . . . . .
H3 H 0.0116 0.3769 1.2752 0.082 Uiso 1 1 calc R U . . .
C4 C 0.02987(9) 0.42784(9) 1.0392(3) 0.0538(5) Uani 1 1 d . . . . .
C5 C 0.01908(9) 0.48147(9) 0.9510(3) 0.0513(5) Uani 1 1 d . . . . .
C6 C 0.06969(10) 0.38841(9) 0.9393(3) 0.0553(5) Uani 1 1 d . . . . .
C7 C 0.08489(11) 0.46001(10) 0.6639(4) 0.0599(6) Uani 1 1 d . . . . .
C8 C 0.12992(9) 0.36820(9) 0.6488(3) 0.0482(5) Uani 1 1 d . . . . .
C9 C 0.10698(9) 0.32312(8) 0.5464(3) 0.0482(5) Uani 1 1 d . . . . .
H9 H 0.0682 0.3162 0.5491 0.058 Uiso 1 1 calc R U . . .
C10 C 0.14325(8) 0.28842(9) 0.4393(3) 0.0468(5) Uani 1 1 d . . . . .
H10 H 0.1279 0.2578 0.3695 0.056 Uiso 1 1 calc R U . . .
C11 C 0.22091(8) 0.34001(9) 0.5384(3) 0.0493(5) Uani 1 1 d . . . . .
H11 H 0.2599 0.3453 0.5382 0.059 Uiso 1 1 calc R U . . .
C12 C 0.18816(9) 0.37719(9) 0.6494(3) 0.0522(5) Uani 1 1 d . . . . .
H12 H 0.2043 0.4070 0.7216 0.063 Uiso 1 1 calc R U . . .
N1 N 0.09336(8) 0.40720(7) 0.7546(3) 0.0516(4) Uani 1 1 d . . . . .
N2 N 0.19951(6) 0.29624(6) 0.4297(2) 0.0419(4) Uani 1 1 d . . . . .


_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 N2 2.0007(15) . ?
Cu1 N2 2.0008(15) 8_656 ?
Cu1 N2 2.0008(15) 3 ?
Cu1 N2 2.0008(15) 6_566 ?
O2 C6 1.212(3) . ?
O1 C7 1.223(3) . ?
C1 C2 1.379(3) . ?
C1 C5 1.408(3) 5_567 ?
C1 C7 1.472(3) 5_567 ?
C2 C3 1.394(3) . ?
C3 C4 1.373(3) . ?
C4 C5 1.416(3) . ?
C4 C6 1.477(3) . ?
C5 C1 1.408(3) 5_567 ?
C5 C5 1.411(4) 5_567 ?
C6 N1 1.405(3) . ?
C7 N1 1.396(3) . ?
C7 C1 1.472(3) 5_567 ?
C8 C9 1.370(3) . ?
C8 C12 1.392(3) . ?
C8 N1 1.440(2) . ?
C9 C10 1.378(3) . ?
C10 N2 1.343(2) . ?
C11 N2 1.353(3) . ?
C11 C12 1.378(3) . ?

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
N2 Cu1 N2 110.31(5) . 8_656 ?
N2 Cu1 N2 107.81(9) . 3 ?
N2 Cu1 N2 110.31(5) 8_656 3 ?
N2 Cu1 N2 110.31(5) . 6_566 ?
N2 Cu1 N2 107.81(9) 8_656 6_566 ?
N2 Cu1 N2 110.31(5) 3 6_566 ?
C2 C1 C5 120.03(19) . 5_567 ?
C2 C1 C7 120.1(2) . 5_567 ?
C5 C1 C7 119.87(19) 5_567 5_567 ?
C1 C2 C3 120.9(2) . . ?
C4 C3 C2 119.9(2) . . ?
C3 C4 C5 120.7(2) . . ?
C3 C4 C6 119.4(2) . . ?
C5 C4 C6 119.82(19) . . ?
C1 C5 C5 119.4(2) 5_567 5_567 ?
C1 C5 C4 121.63(19) 5_567 . ?
C5 C5 C4 118.9(2) 5_567 . ?
O2 C6 N1 120.54(19) . . ?
O2 C6 C4 123.5(2) . . ?
N1 C6 C4 115.90(18) . . ?
O1 C7 N1 120.5(2) . . ?
O1 C7 C1 123.1(2) . 5_567 ?
N1 C7 C1 116.41(19) . 5_567 ?
C9 C8 C12 120.71(19) . . ?
C9 C8 N1 119.73(19) . . ?
C12 C8 N1 119.56(19) . . ?
C8 C9 C10 117.79(19) . . ?
N2 C10 C9 123.85(18) . . ?
N2 C11 C12 123.73(18) . . ?
C11 C12 C8 117.13(19) . . ?
C7 N1 C6 126.29(17) . . ?
C7 N1 C8 116.85(17) . . ?
C6 N1 C8 116.86(17) . . ?
C10 N2 C11 116.73(16) . . ?
C10 N2 Cu1 122.82(13) . . ?
C11 N2 Cu1 120.31(13) . . ?

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
C5 C1 C2 C3 -0.2(5) 5_567 . . . ?
C7 C1 C2 C3 -179.1(3) 5_567 . . . ?
C1 C2 C3 C4 -0.3(5) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C2 C3 C4 C6 -179.8(3) . . . . ?
C3 C4 C5 C1 179.5(2) . . . 5_567 ?
C6 C4 C5 C1 -0.1(4) . . . 5_567 ?
C3 C4 C5 C5 -0.4(4) . . . 5_567 ?
C6 C4 C5 C5 -180.0(3) . . . 5_567 ?
C3 C4 C6 O2 -0.3(4) . . . . ?
C5 C4 C6 O2 179.3(2) . . . . ?
C3 C4 C6 N1 178.6(2) . . . . ?
C5 C4 C6 N1 -1.9(3) . . . . ?
C12 C8 C9 C10 -2.1(3) . . . . ?
N1 C8 C9 C10 176.99(18) . . . . ?
C8 C9 C10 N2 0.0(3) . . . . ?
N2 C11 C12 C8 0.5(3) . . . . ?
C9 C8 C12 C11 1.9(3) . . . . ?
N1 C8 C12 C11 -177.24(19) . . . . ?
O1 C7 N1 C6 177.8(2) . . . . ?
C1 C7 N1 C6 -2.6(4) 5_567 . . . ?
O1 C7 N1 C8 -2.1(4) . . . . ?
C1 C7 N1 C8 177.4(2) 5_567 . . . ?
O2 C6 N1 C7 -177.8(2) . . . . ?
C4 C6 N1 C7 3.3(4) . . . . ?
O2 C6 N1 C8 2.1(3) . . . . ?
C4 C6 N1 C8 -176.72(19) . . . . ?
C9 C8 N1 C7 -105.3(2) . . . . ?
C12 C8 N1 C7 73.8(3) . . . . ?
C9 C8 N1 C6 74.7(3) . . . . ?
C12 C8 N1 C6 -106.1(2) . . . . ?
C9 C10 N2 C11 2.2(3) . . . . ?
C9 C10 N2 Cu1 -173.48(15) . . . . ?
C12 C11 N2 C10 -2.5(3) . . . . ?
C12 C11 N2 Cu1 173.34(17) . . . . ?

_refine_diff_density_max         0.264
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.045



