# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1554621'
_audit_update_record             
;
2017-06-07 deposited with the CCDC.
2018-01-19 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            'C6 H5 Cu5 I4 N10'
_chemical_formula_weight         1042.55

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   6.9852(2)
_cell_length_b                   17.8187(6)
_cell_length_c                   8.5879(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.313(2)
_cell_angle_gamma                90
_cell_volume                     1044.32(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2083
_cell_measurement_theta_min      2.4226
_cell_measurement_theta_max      28.5129

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    3.316
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    10.933
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.364
_exptl_absorpt_correction_T_max  0.646
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.2083
_diffrn_reflns_number            3551
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.427
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_full        24.992
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measured_fraction_theta_full 0.939
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_Laue_measured_fraction_full 0.939
_diffrn_reflns_point_group_measured_fraction_max 0.701
_diffrn_reflns_point_group_measured_fraction_full 0.701
_reflns_number_total             3551
_reflns_number_gt                2434
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.443
_reflns_Friedel_fraction_max     0.446
_reflns_Friedel_fraction_full    0.446

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0489P)²+0.2292P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 683 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(6)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         2584
_refine_ls_number_parameters     221
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0982
_refine_ls_wR_factor_gt          0.0961
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.108
_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
I4 I 1.55718(15) 0.75110(8) 1.85037(14) 0.0292(4) Uani 1 1 d . . . . .
I1 I 1.48605(17) 0.96434(8) 1.61820(18) 0.0376(4) Uani 1 1 d . . . . .
I3 I 1.99529(16) 0.83805(7) 1.62803(16) 0.0345(4) Uani 1 1 d . . . . .
I2 I 2.05196(16) 1.04882(9) 1.86878(15) 0.0331(4) Uani 1 1 d . . . . .
Cu4 Cu 1.7683(3) 0.71858(16) 1.6455(2) 0.0281(6) Uani 1 1 d . . . . .
Cu2 Cu 1.7321(3) 1.15390(17) 2.0133(3) 0.0249(5) Uani 1 1 d . . . . .
Cu1 Cu 1.2606(3) 1.07882(15) 1.6548(3) 0.0281(6) Uani 1 1 d . . . . .
Cu3 Cu 1.8549(3) 0.97436(17) 1.6098(3) 0.0328(6) Uani 1 1 d . . . . .
Cu5 Cu 1.3582(3) 0.82665(17) 1.5905(3) 0.0341(7) Uani 1 1 d . . . . .
N4 N 1.0492(19) 1.0861(9) 1.4531(16) 0.019(3) Uani 1 1 d . . . . .
N8 N 1.4468(18) 1.1672(10) 1.6803(15) 0.018(3) Uani 1 1 d . U . . .
N7 N 1.596(2) 1.1894(9) 1.7996(16) 0.023(3) Uani 1 1 d . . . . .
N6 N 1.906(2) 1.2427(11) 1.9932(16) 0.034(4) Uani 1 1 d . . . . .
C6 C 1.672(2) 1.2483(12) 1.750(2) 0.028(4) Uani 1 1 d . . . . .
C5 C 1.821(3) 1.2909(13) 1.861(2) 0.047(5) Uani 1 1 d D U . . .
H5 H 1.7432 1.3263 1.9088 0.056 Uiso 1 1 calc R U . . .
N10 N 1.585(2) 1.2660(11) 1.6003(17) 0.029(4) Uani 1 1 d . . . . .
N9 N 1.4410(19) 1.2131(9) 1.5612(16) 0.021(3) Uani 1 1 d . . . . .
C1 C 0.598(3) 0.9439(11) 1.181(3) 0.048(6) Uani 1 1 d . . . . .
H1A H 0.6139 0.9250 1.2881 0.072 Uiso 1 1 calc R U . . .
H1B H 0.4746 0.9271 1.1188 0.072 Uiso 1 1 calc R U . . .
H1C H 0.7023 0.9258 1.1349 0.072 Uiso 1 1 calc R U . . .
N3 N 1.0398(17) 1.1320(10) 1.3353(15) 0.016(3) Uani 1 1 d . U . . .
N5 N 0.8938(19) 1.0393(10) 1.4225(16) 0.020(3) Uani 1 1 d . U . . .
N2 N 0.8796(18) 1.1166(9) 1.2248(15) 0.016(3) Uani 1 1 d . . . . .
C3 C 0.794(2) 1.0597(11) 1.2808(17) 0.017(4) Uani 1 1 d . . . . .
C2 C 0.602(2) 1.0289(9) 1.1851(17) 0.016(3) Uani 1 1 d . U . . .
H2 H 0.4945 1.0468 1.2326 0.020 Uiso 1 1 calc R U . . .
N1 N 0.5776(18) 1.0602(9) 1.0250(16) 0.021(3) Uani 1 1 d . U . . .
C4 C 1.965(5) 1.341(2) 1.806(4) 0.107(12) Uiso 1 1 d 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
I4 Cu4 2.591(2) . ?
I4 Cu5 2.720(3) . ?
I4 Cu2 3.076(3) 2_849 ?
I1 Cu3 2.599(2) . ?
I1 Cu5 2.604(3) . ?
I1 Cu1 2.636(3) . ?
I3 Cu3 2.611(3) . ?
I3 Cu5 2.631(3) 1_655 ?
I3 Cu4 2.678(3) . ?
I2 Cu1 2.632(2) 1_655 ?
I2 Cu3 2.701(3) . ?
Cu4 N3 2.027(16) 2_848 ?
Cu4 N9 2.047(13) 2_848 ?
Cu2 N7 1.982(14) . ?
Cu2 N2 2.001(13) 1_656 ?
Cu2 N1 2.002(15) 1_656 ?
Cu2 N6 2.024(16) . ?
Cu2 I4 3.076(3) 2_859 ?
Cu1 N8 2.025(16) . ?
Cu1 N4 2.027(14) . ?
Cu1 I2 2.632(2) 1_455 ?
Cu3 N5 2.046(15) 1_655 ?
Cu5 N10 2.071(16) 2_848 ?
Cu5 I3 2.631(3) 1_455 ?
N4 N3 1.29(2) . ?
N4 N5 1.349(19) . ?
N8 N9 1.30(2) . ?
N8 N7 1.354(19) . ?
N7 C6 1.29(2) . ?
N6 C5 1.45(3) . ?
C6 N10 1.33(2) . ?
C6 C5 1.47(3) . ?
C5 C4 1.49(2) . ?
N10 N9 1.37(2) . ?
N10 Cu5 2.071(16) 2_858 ?
N9 Cu4 2.047(13) 2_858 ?
C1 C2 1.51(2) . ?
N3 N2 1.332(17) . ?
N3 Cu4 2.027(16) 2_858 ?
N5 C3 1.32(2) . ?
N5 Cu3 2.046(14) 1_455 ?
N2 C3 1.32(2) . ?
N2 Cu2 2.001(13) 1_454 ?
C3 C2 1.521(19) . ?
C2 N1 1.46(2) . ?
N1 Cu2 2.002(15) 1_454 ?

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
Cu4 I4 Cu5 79.56(8) . . ?
Cu4 I4 Cu2 130.37(10) . 2_849 ?
Cu5 I4 Cu2 109.20(8) . 2_849 ?
Cu3 I1 Cu5 112.63(11) . . ?
Cu3 I1 Cu1 124.82(10) . . ?
Cu5 I1 Cu1 122.55(9) . . ?
Cu3 I3 Cu5 115.07(11) . 1_655 ?
Cu3 I3 Cu4 121.58(9) . . ?
Cu5 I3 Cu4 122.89(9) 1_655 . ?
Cu1 I2 Cu3 77.63(8) 1_655 . ?
N3 Cu4 N9 111.8(6) 2_848 2_848 ?
N3 Cu4 I4 125.3(4) 2_848 . ?
N9 Cu4 I4 101.2(4) 2_848 . ?
N3 Cu4 I3 102.7(4) 2_848 . ?
N9 Cu4 I3 108.1(5) 2_848 . ?
I4 Cu4 I3 106.85(10) . . ?
N7 Cu2 N2 177.5(6) . 1_656 ?
N7 Cu2 N1 98.9(6) . 1_656 ?
N2 Cu2 N1 81.7(6) 1_656 1_656 ?
N7 Cu2 N6 81.4(6) . . ?
N2 Cu2 N6 97.8(6) 1_656 . ?
N1 Cu2 N6 174.7(8) 1_656 . ?
N7 Cu2 I4 87.0(4) . 2_859 ?
N2 Cu2 I4 95.4(4) 1_656 2_859 ?
N1 Cu2 I4 92.6(4) 1_656 2_859 ?
N6 Cu2 I4 92.7(5) . 2_859 ?
N8 Cu1 N4 112.1(6) . . ?
N8 Cu1 I2 121.4(4) . 1_455 ?
N4 Cu1 I2 101.5(4) . 1_455 ?
N8 Cu1 I1 103.2(4) . . ?
N4 Cu1 I1 107.0(5) . . ?
I2 Cu1 I1 111.09(11) 1_455 . ?
N5 Cu3 I1 111.0(4) 1_655 . ?
N5 Cu3 I3 117.5(5) 1_655 . ?
I1 Cu3 I3 107.23(11) . . ?
N5 Cu3 I2 103.9(5) 1_655 . ?
I1 Cu3 I2 110.18(10) . . ?
I3 Cu3 I2 106.78(10) . . ?
N10 Cu5 I1 116.4(5) 2_848 . ?
N10 Cu5 I3 119.3(4) 2_848 1_455 ?
I1 Cu5 I3 103.68(10) . 1_455 ?
N10 Cu5 I4 103.9(5) 2_848 . ?
I1 Cu5 I4 106.62(9) . . ?
I3 Cu5 I4 105.95(10) 1_455 . ?
N3 N4 N5 109.5(13) . . ?
N3 N4 Cu1 128.0(11) . . ?
N5 N4 Cu1 122.5(11) . . ?
N9 N8 N7 107.6(14) . . ?
N9 N8 Cu1 119.5(10) . . ?
N7 N8 Cu1 132.9(11) . . ?
C6 N7 N8 106.7(14) . . ?
C6 N7 Cu2 114.7(12) . . ?
N8 N7 Cu2 138.4(12) . . ?
C5 N6 Cu2 112.3(11) . . ?
N7 C6 N10 112.2(17) . . ?
N7 C6 C5 119.3(16) . . ?
N10 C6 C5 128.2(19) . . ?
N6 C5 C6 108.7(17) . . ?
N6 C5 C4 114(2) . . ?
C6 C5 C4 122(2) . . ?
C6 N10 N9 103.5(16) . . ?
C6 N10 Cu5 139.4(13) . 2_858 ?
N9 N10 Cu5 114.9(10) . 2_858 ?
N8 N9 N10 110.0(13) . . ?
N8 N9 Cu4 127.4(11) . 2_858 ?
N10 N9 Cu4 122.2(11) . 2_858 ?
N4 N3 N2 108.8(14) . . ?
N4 N3 Cu4 119.7(10) . 2_858 ?
N2 N3 Cu4 131.0(12) . 2_858 ?
C3 N5 N4 104.7(14) . . ?
C3 N5 Cu3 138.6(12) . 1_455 ?
N4 N5 Cu3 115.6(10) . 1_455 ?
C3 N2 N3 106.0(13) . . ?
C3 N2 Cu2 113.6(10) . 1_454 ?
N3 N2 Cu2 140.3(12) . 1_454 ?
N2 C3 N5 111.0(14) . . ?
N2 C3 C2 119.9(14) . . ?
N5 C3 C2 129.1(15) . . ?
N1 C2 C1 111.4(15) . . ?
N1 C2 C3 106.4(12) . . ?
C1 C2 C3 112.5(14) . . ?
C2 N1 Cu2 114.3(10) . 1_454 ?

_refine_diff_density_max         1.100
_refine_diff_density_min         -0.923
_refine_diff_density_rms         0.224

####################################################################### 
# 
# 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 1554622'
_audit_update_record             
;
2017-06-07 deposited with the CCDC.
2018-01-19 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            'C12 H16 Cu6 I4 N20'
_chemical_formula_weight         1329.35

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   9.0012(6)
_cell_length_b                   14.3269(10)
_cell_length_c                   12.5315(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.300(6)
_cell_angle_gamma                90
_cell_volume                     1611.50(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2572
_cell_measurement_theta_min      0.410
_cell_measurement_theta_max      0.678

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.740
_exptl_crystal_F_000             1228
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    7.762
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.83049
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.2083
_diffrn_reflns_number            6201
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.678
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.725
_diffrn_reflns_point_group_measured_fraction_full 0.725
_reflns_number_total             4113
_reflns_number_gt                3605
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.390
_reflns_Friedel_fraction_max     0.425
_reflns_Friedel_fraction_full    0.425

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0798P)²+4.2052P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 920 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(5)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         4113
_refine_ls_number_parameters     355
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1364
_refine_ls_wR_factor_gt          0.1304
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.053
_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
I4 I 0.10108(14) 0.02207(13) 1.12068(10) 0.0310(4) Uani 1 1 d . . . . .
I1 I 0.88833(13) 0.13036(12) 0.38241(10) 0.0309(4) Uani 1 1 d . . . . .
I2 I 0.66336(17) 0.00002(11) 0.63932(12) 0.0387(5) Uani 1 1 d . . . . .
I3 I 0.34226(15) 0.15059(10) 0.86713(11) 0.0290(4) Uani 1 1 d . . . . .
Cu3 Cu 0.5323(3) 0.1659(2) 0.7270(2) 0.0295(7) Uani 1 1 d . . . . .
Cu1 Cu 0.1017(2) 0.3146(2) 0.36995(19) 0.0234(6) Uani 1 1 d . . . . .
Cu6 Cu 1.1181(2) 0.3259(2) 0.86836(19) 0.0243(6) Uani 1 1 d . . . . .
Cu4 Cu 0.4704(2) -0.0058(2) 0.77659(19) 0.0261(7) Uani 1 1 d . . . . .
Cu2 Cu 0.6792(3) 0.1410(3) 0.4981(2) 0.0659(13) Uani 1 1 d . . . . .
Cu5 Cu 0.2920(3) -0.0134(2) 0.9923(2) 0.0326(7) Uani 1 1 d . . . . .
N5 N 0.4771(16) 0.1966(13) 0.4910(13) 0.022(4) Uani 1 1 d . U . . .
N15 N 0.5101(17) -0.0497(13) 1.0093(13) 0.021(4) Uani 1 1 d . U . . .
N16 N 1.0080(17) 0.2516(14) 0.9772(12) 0.024(5) Uani 1 1 d . . . . .
N1 N 0.2181(17) 0.2497(14) 0.2548(13) 0.026(4) Uani 1 1 d . . . . .
N20 N 0.7322(17) 0.2288(13) 0.7466(12) 0.0223(19) Uani 1 1 d . . . . .
N10 N 0.2684(16) -0.0626(12) 0.7592(13) 0.023(4) Uani 1 1 d . . . . .
N17 N 0.9557(17) 0.2815(14) 0.7719(11) 0.0223(19) Uani 1 1 d . . . . .
N2 N 0.2629(16) 0.2639(13) 0.4669(12) 0.023(4) Uani 1 1 d . . . . .
N4 N 0.4249(16) 0.2184(14) 0.5843(12) 0.023(4) Uani 1 1 d . . . . .
C9 C 0.6092(18) -0.0877(15) 1.0814(16) 0.019(4) Uani 1 1 d . . . . .
N14 N 0.5689(16) -0.0626(13) 0.9138(12) 0.022(4) Uani 1 1 d . . . . .
C3 C 0.3683(18) 0.2177(15) 0.4183(15) 0.019(4) Uani 1 1 d . . . . .
N9 N 0.2057(16) -0.0833(12) 0.8537(11) 0.0223(19) Uani 1 1 d . . . . .
N19 N 0.7757(18) 0.2617(19) 0.6563(13) 0.063(8) Uani 1 1 d . . . . .
N13 N 0.7021(18) -0.1001(14) 0.9284(12) 0.028(4) Uani 1 1 d . . . . .
N3 N 0.2976(16) 0.2611(13) 0.5710(12) 0.020(4) Uani 1 1 d . U . . .
C2 C 0.3547(18) 0.2038(15) 0.3028(12) 0.0223(19) Uani 1 1 d . . . . .
H2 H 0.3442 0.1366 0.2896 0.027 Uiso 1 1 calc R U . . .
C6 C 0.1669(18) -0.0948(13) 0.6836(14) 0.015(4) Uani 1 1 d . . . . .
C12 C 0.849(2) 0.2338(17) 0.8166(15) 0.0223(19) Uani 1 1 d . . . . .
C8 C 0.6056(16) -0.0965(14) 1.2011(12) 0.017(4) Uani 1 1 d . . . . .
H8 H 0.5505 -0.1538 1.2144 0.020 Uiso 1 1 calc R U . . .
N8 N 0.0755(18) -0.1229(14) 0.8362(12) 0.030(4) Uani 1 1 d . . . . .
N18 N 0.9106(19) 0.295(2) 0.6710(14) 0.062(8) Uani 1 1 d . . . . .
C1 C 0.4954(19) 0.2386(16) 0.2445(14) 0.031(5) Uani 1 1 d . . . . .
H1A H 0.4792 0.2274 0.1690 0.047 Uiso 1 1 calc R U . . .
H1B H 0.5096 0.3042 0.2571 0.047 Uiso 1 1 calc R U . . .
H1C H 0.5823 0.2051 0.2723 0.047 Uiso 1 1 calc R U . . .
C11 C 0.8759(17) 0.2004(14) 0.9293(13) 0.019(4) Uani 1 1 d . . . . .
H11 H 0.9033 0.1343 0.9263 0.022 Uiso 1 1 calc R U . . .
C5 C 0.1660(18) -0.0951(15) 0.5665(14) 0.025(4) Uani 1 1 d . . . . .
H5 H 0.2269 -0.1479 0.5458 0.030 Uiso 1 1 calc R U . . .
C10 C 0.744(2) 0.207(2) 0.9949(15) 0.058(9) Uani 1 1 d . . . . .
H10A H 0.7700 0.1847 1.0659 0.087 Uiso 1 1 calc R U . . .
H10B H 0.7127 0.2714 0.9984 0.087 Uiso 1 1 calc R U . . .
H10C H 0.6634 0.1705 0.9624 0.087 Uiso 1 1 calc R U . . .
C4 C 0.233(2) -0.0060(17) 0.5231(16) 0.041(6) Uani 1 1 d . . . . .
H4A H 0.2306 -0.0093 0.4465 0.062 Uiso 1 1 calc R U . . .
H4B H 0.1772 0.0470 0.5438 0.062 Uiso 1 1 calc R U . . .
H4C H 0.3349 0.0000 0.5519 0.062 Uiso 1 1 calc R U . . .
C7 C 0.530(2) -0.0200(17) 1.2547(17) 0.044(5) Uani 1 1 d . U . . .
H7A H 0.4297 -0.0143 1.2241 0.065 Uiso 1 1 calc R U . . .
H7B H 0.5296 -0.0334 1.3297 0.065 Uiso 1 1 calc R U . . .
H7C H 0.5825 0.0374 1.2451 0.065 Uiso 1 1 calc R U . . .
N12 N 0.7285(17) -0.1152(13) 1.0363(11) 0.022(4) Uani 1 1 d . . . . .
N6 N 0.0102(16) -0.1127(13) 0.5236(11) 0.016(4) Uani 1 1 d . . . . .
N11 N 0.7637(15) -0.1136(14) 1.2407(12) 0.018(4) Uani 1 1 d . U . . .
N7 N 0.0515(17) -0.1297(15) 0.7292(11) 0.026(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
I4 Cu5 2.493(3) . ?
I1 Cu2 2.466(3) . ?
I2 Cu4 2.536(3) . ?
I2 Cu2 2.695(4) . ?
I2 Cu3 2.905(4) . ?
I3 Cu3 2.551(3) . ?
I3 Cu4 2.799(3) . ?
I3 Cu5 2.880(3) . ?
Cu3 N20 2.011(16) . ?
Cu3 N4 2.107(15) . ?
Cu3 Cu4 2.608(3) . ?
Cu1 N2 1.962(14) . ?
Cu1 N7 1.955(15) 2_556 ?
Cu1 N6 2.020(15) 2_556 ?
Cu1 N1 2.067(18) . ?
Cu6 N17 1.933(15) . ?
Cu6 N12 1.949(15) 2_757 ?
Cu6 N11 1.991(16) 2_757 ?
Cu6 N16 2.045(18) . ?
Cu4 N10 1.989(15) . ?
Cu4 N14 2.043(15) . ?
Cu2 N5 1.981(15) . ?
Cu5 N15 2.026(15) . ?
Cu5 N9 2.102(16) . ?
N5 N4 1.33(2) . ?
N5 C3 1.32(2) . ?
N15 C9 1.34(2) . ?
N15 N14 1.36(2) . ?
N16 C11 1.49(2) . ?
N1 C2 1.48(2) . ?
N20 N19 1.31(2) . ?
N20 C12 1.32(2) . ?
N10 C6 1.35(2) . ?
N10 N9 1.38(2) . ?
N17 N18 1.31(2) . ?
N17 C12 1.34(2) . ?
N2 N3 1.32(2) . ?
N2 C3 1.34(2) . ?
N4 N3 1.30(2) . ?
C9 N12 1.31(2) . ?
C9 C8 1.51(2) . ?
N14 N13 1.31(2) . ?
C3 C2 1.46(2) . ?
N9 N8 1.31(2) . ?
N19 N18 1.31(2) . ?
N13 N12 1.37(2) . ?
C2 C1 1.59(2) . ?
C6 N7 1.32(2) . ?
C6 C5 1.47(2) . ?
C12 C11 1.49(2) . ?
C8 C7 1.48(3) . ?
C8 N11 1.492(19) . ?
N8 N7 1.35(2) . ?
C11 C10 1.50(3) . ?
C5 N6 1.49(2) . ?
C5 C4 1.53(3) . ?
N12 Cu6 1.949(15) 2_747 ?
N6 Cu1 2.020(15) 2_546 ?
N11 Cu6 1.991(16) 2_747 ?
N7 Cu1 1.956(15) 2_546 ?

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
Cu4 I2 Cu2 122.86(11) . . ?
Cu4 I2 Cu3 56.80(8) . . ?
Cu2 I2 Cu3 71.23(10) . . ?
Cu3 I3 Cu4 58.13(8) . . ?
Cu3 I3 Cu5 125.87(10) . . ?
Cu4 I3 Cu5 69.74(9) . . ?
N20 Cu3 N4 107.1(7) . . ?
N20 Cu3 I3 126.5(5) . . ?
N4 Cu3 I3 109.1(4) . . ?
N20 Cu3 Cu4 126.8(5) . . ?
N4 Cu3 Cu4 116.5(5) . . ?
I3 Cu3 Cu4 65.70(9) . . ?
N20 Cu3 I2 91.6(5) . . ?
N4 Cu3 I2 98.3(5) . . ?
I3 Cu3 I2 120.14(13) . . ?
Cu4 Cu3 I2 54.44(8) . . ?
N2 Cu1 N7 176.9(8) . 2_556 ?
N2 Cu1 N6 99.5(6) . 2_556 ?
N7 Cu1 N6 81.2(6) 2_556 2_556 ?
N2 Cu1 N1 82.8(6) . . ?
N7 Cu1 N1 96.3(7) 2_556 . ?
N6 Cu1 N1 175.6(8) 2_556 . ?
N17 Cu6 N12 173.4(9) . 2_757 ?
N17 Cu6 N11 97.6(6) . 2_757 ?
N12 Cu6 N11 80.9(7) 2_757 2_757 ?
N17 Cu6 N16 82.2(6) . . ?
N12 Cu6 N16 100.0(6) 2_757 . ?
N11 Cu6 N16 174.2(9) 2_757 . ?
N10 Cu4 N14 105.4(7) . . ?
N10 Cu4 I2 127.3(5) . . ?
N14 Cu4 I2 107.9(4) . . ?
N10 Cu4 Cu3 124.7(5) . . ?
N14 Cu4 Cu3 119.3(5) . . ?
I2 Cu4 Cu3 68.76(9) . . ?
N10 Cu4 I3 88.3(5) . . ?
N14 Cu4 I3 98.3(5) . . ?
I2 Cu4 I3 124.92(12) . . ?
Cu3 Cu4 I3 56.17(8) . . ?
N5 Cu2 I1 137.5(5) . . ?
N5 Cu2 I2 103.7(5) . . ?
I1 Cu2 I2 114.84(14) . . ?
N15 Cu5 N9 105.1(6) . . ?
N15 Cu5 I4 133.9(5) . . ?
N9 Cu5 I4 113.6(4) . . ?
N15 Cu5 I3 94.4(5) . . ?
N9 Cu5 I3 90.1(5) . . ?
I4 Cu5 I3 109.21(12) . . ?
N4 N5 C3 105.0(15) . . ?
N4 N5 Cu2 116.1(11) . . ?
C3 N5 Cu2 138.8(14) . . ?
C9 N15 N14 104.9(15) . . ?
C9 N15 Cu5 140.1(14) . . ?
N14 N15 Cu5 112.4(11) . . ?
C11 N16 Cu6 113.6(11) . . ?
C2 N1 Cu1 111.4(11) . . ?
N19 N20 C12 106.2(16) . . ?
N19 N20 Cu3 112.2(12) . . ?
C12 N20 Cu3 140.0(14) . . ?
C6 N10 N9 103.3(14) . . ?
C6 N10 Cu4 141.6(13) . . ?
N9 N10 Cu4 115.0(11) . . ?
N18 N17 C12 107.4(16) . . ?
N18 N17 Cu6 135.9(14) . . ?
C12 N17 Cu6 116.1(12) . . ?
N3 N2 C3 108.1(14) . . ?
N3 N2 Cu1 137.2(13) . . ?
C3 N2 Cu1 114.7(12) . . ?
N3 N4 N5 111.4(14) . . ?
N3 N4 Cu3 128.4(12) . . ?
N5 N4 Cu3 119.5(12) . . ?
N12 C9 N15 110.9(17) . . ?
N12 C9 C8 118.9(15) . . ?
N15 C9 C8 130.1(17) . . ?
N13 N14 N15 110.1(14) . . ?
N13 N14 Cu4 127.9(12) . . ?
N15 N14 Cu4 121.0(12) . . ?
N5 C3 N2 108.2(17) . . ?
N5 C3 C2 131.0(17) . . ?
N2 C3 C2 120.6(16) . . ?
N8 N9 N10 111.6(14) . . ?
N8 N9 Cu5 128.1(12) . . ?
N10 N9 Cu5 117.2(11) . . ?
N18 N19 N20 110.2(16) . . ?
N14 N13 N12 106.9(15) . . ?
N4 N3 N2 106.4(15) . . ?
C3 C2 N1 110.4(15) . . ?
C3 C2 C1 113.8(14) . . ?
N1 C2 C1 109.9(15) . . ?
N7 C6 N10 109.9(15) . . ?
N7 C6 C5 119.0(16) . . ?
N10 C6 C5 131.1(16) . . ?
N20 C12 N17 108.1(16) . . ?
N20 C12 C11 132.6(17) . . ?
N17 C12 C11 119.3(16) . . ?
C7 C8 N11 115.5(15) . . ?
C7 C8 C9 115.8(16) . . ?
N11 C8 C9 104.7(13) . . ?
N9 N8 N7 105.9(15) . . ?
N19 N18 N17 107.4(17) . . ?
C12 C11 N16 107.0(15) . . ?
C12 C11 C10 114.7(16) . . ?
N16 C11 C10 112.9(16) . . ?
C6 C5 N6 107.3(14) . . ?
C6 C5 C4 112.3(17) . . ?
N6 C5 C4 113.7(15) . . ?
C9 N12 N13 106.9(15) . . ?
C9 N12 Cu6 115.6(12) . 2_747 ?
N13 N12 Cu6 137.2(13) . 2_747 ?
C5 N6 Cu1 110.6(10) . 2_546 ?
C8 N11 Cu6 112.9(11) . 2_747 ?
C6 N7 N8 109.3(15) . . ?
C6 N7 Cu1 114.9(12) . 2_546 ?
N8 N7 Cu1 135.7(14) . 2_546 ?

_refine_diff_density_max         3.814
_refine_diff_density_min         -0.978
_refine_diff_density_rms         0.271

