# Electronic Supplementary Material (ESI) for ChemComm.
# 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 1851345'
_audit_update_record             
;
2018-06-25 deposited with the CCDC.
2018-08-17 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            'C7 H8 Cu4 I4 N5'
_chemical_formula_weight         923.94

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      orthorhombic
_space_group_IT_number           52
_space_group_name_H-M_alt        'P n n a'
_space_group_name_Hall           '-P 2a 2bc'

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

_cell_length_a                   14.8153(12)
_cell_length_b                   14.3340(12)
_cell_length_c                   11.4471(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2430.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5760
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      27.45

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.525
_exptl_crystal_F_000             1652
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    8.527
_shelx_estimated_absorpt_T_min   0.361
_shelx_estimated_absorpt_T_max   0.483
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19213
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.277
_diffrn_reflns_theta_max         28.708
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3084
_reflns_number_gt                2392
_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       ?
_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)+(0.0481P)²+10.5824P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3084
_refine_ls_number_parameters     120
_refine_ls_number_restraints     41
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.1094
_refine_ls_wR_factor_gt          0.1005
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.009
_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
C1 C 0.0637(3) 0.2096(4) 0.7179(5) 0.0351(12) Uani 1 1 d . . . . .
C2 C 0.4882(4) 0.1570(4) 0.3216(6) 0.0425(14) Uani 1 1 d . . . . .
C3 C 0.2000(5) 0.2500 0.7500 0.043(2) Uani 1 2 d S T P . .
H3 H 0.2627 0.2500 0.7500 0.051 Uiso 1 2 calc R U P . .
C4A C 0.105(7) 0.102(8) 0.060(18) 0.32(2) Uani 0.191(18) 1 d D U P A 1
H4A1 H 0.0774 0.1454 0.0066 0.480 Uiso 0.191(18) 1 d R U P A 1
H4A2 H 0.0661 0.0490 0.0696 0.480 Uiso 0.191(18) 1 d R U P A 1
H4A3 H 0.1138 0.1319 0.1341 0.480 Uiso 0.191(18) 1 d R U P A 1
C5A C 0.197(7) 0.072(10) 0.009(14) 0.330(19) Uani 0.191(18) 1 d D U P A 1
H5A1 H 0.1863 0.0444 -0.0670 0.396 Uiso 0.191(18) 1 d R U P A 1
H5A2 H 0.2339 0.1271 -0.0027 0.396 Uiso 0.191(18) 1 d R U P A 1
C5B C 0.266(7) 0.093(4) 0.020(10) 0.329(19) Uani 0.309(18) 1 d D U P A 2
H5B1 H 0.2111 0.1295 0.0268 0.395 Uiso 0.309(18) 1 d R U P A 2
H5B2 H 0.2730 0.0777 -0.0625 0.395 Uiso 0.309(18) 1 d R U P A 2
C4B C 0.347(6) 0.151(5) 0.059(11) 0.31(2) Uani 0.309(18) 1 d D U P A 2
H4B1 H 0.3485 0.2054 0.0108 0.459 Uiso 0.309(18) 1 d R U P A 2
H4B2 H 0.3408 0.1691 0.1396 0.459 Uiso 0.309(18) 1 d R U P A 2
H4B3 H 0.4029 0.1170 0.0500 0.459 Uiso 0.309(18) 1 d R U P A 2
Cu3 Cu 0.20295(5) 0.07769(5) 0.60480(8) 0.0473(2) Uani 1 1 d . . . . .
Cu4 Cu 0.32897(6) 0.05036(6) 0.43745(9) 0.0543(2) Uani 1 1 d . . . . .
I1 I 0.38080(3) 0.07951(3) 0.66170(5) 0.05011(15) Uani 1 1 d . . . . .
I2 I 0.17156(3) 0.13026(3) 0.37833(5) 0.05635(16) Uani 1 1 d . . . . .
N1 N 0.4263(4) 0.1168(4) 0.3530(6) 0.0553(15) Uani 1 1 d . . . . .
N2 N 0.1515(3) 0.1833(3) 0.6983(5) 0.0390(11) Uani 1 1 d . . . . .
N3 N 0.2500 0.0000 0.068(4) 0.334(19) Uani 1 2 d DS TU P . .
H3A H 0.2882 0.0302 0.1144 0.401 Uiso 0.191(18) 1 calc R U P A 1
H3B H 0.2118 -0.0302 0.1144 0.401 Uiso 0.191(18) 1 calc R U P A 1
H3C H 0.2970 -0.0086 0.1150 0.401 Uiso 0.309(18) 1 calc R U P A 2
H3D H 0.2030 0.0086 0.1150 0.401 Uiso 0.309(18) 1 calc R U P A 2


_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
C1 C1 1.370(10) 4_556 ?
C1 N2 1.373(7) . ?
C1 C2 1.423(8) 6_556 ?
C2 N1 1.142(8) . ?
C2 C1 1.423(8) 6_656 ?
C3 N2 1.334(6) 4_556 ?
C3 N2 1.334(6) . ?
C4A C5A 1.54(2) . ?
C5A N3 1.47(2) . ?
C5B N3 1.46(2) . ?
C5B C4B 1.53(2) . ?
Cu3 N2 2.005(5) . ?
Cu3 Cu3 2.6274(15) 2 ?
Cu3 I1 2.6535(10) 2 ?
Cu3 Cu4 2.6948(12) 2 ?
Cu3 Cu4 2.7035(12) . ?
Cu3 I1 2.7144(9) . ?
Cu3 I2 2.7395(11) . ?
Cu4 N1 1.980(5) . ?
Cu4 I2 2.6760(11) 2 ?
Cu4 I2 2.6849(10) . ?
Cu4 Cu3 2.6948(12) 2 ?
Cu4 I1 2.7118(12) . ?
Cu4 Cu4 2.7496(16) 2 ?
I1 Cu3 2.6535(10) 2 ?
I2 Cu4 2.6759(11) 2 ?
N3 C5B 1.46(2) 2 ?
N3 C5A 1.47(2) 2 ?

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
C1 C1 N2 108.7(3) 4_556 . ?
C1 C1 C2 128.2(3) 4_556 6_556 ?
N2 C1 C2 123.1(5) . 6_556 ?
N1 C2 C1 178.2(6) . 6_656 ?
N2 C3 N2 114.9(7) 4_556 . ?
N3 C5A C4A 120(6) . . ?
N3 C5B C4B 121(6) . . ?
N2 Cu3 Cu3 147.33(16) . 2 ?
N2 Cu3 I1 109.40(15) . 2 ?
Cu3 Cu3 I1 61.86(3) 2 2 ?
N2 Cu3 Cu4 145.80(15) . 2 ?
Cu3 Cu3 Cu4 61.04(3) 2 2 ?
I1 Cu3 Cu4 60.93(3) 2 2 ?
N2 Cu3 Cu4 138.64(16) . . ?
Cu3 Cu3 Cu4 60.71(3) 2 . ?
I1 Cu3 Cu4 111.95(3) 2 . ?
Cu4 Cu3 Cu4 61.24(4) 2 . ?
N2 Cu3 I1 103.52(14) . . ?
Cu3 Cu3 I1 59.54(3) 2 . ?
I1 Cu3 I1 113.78(3) 2 . ?
Cu4 Cu3 I1 110.34(3) 2 . ?
Cu4 Cu3 I1 60.07(3) . . ?
N2 Cu3 I2 103.48(17) . . ?
Cu3 Cu3 I2 108.860(19) 2 . ?
I1 Cu3 I2 112.74(3) 2 . ?
Cu4 Cu3 I2 58.99(3) 2 . ?
Cu4 Cu3 I2 59.11(3) . . ?
I1 Cu3 I2 112.91(3) . . ?
N1 Cu4 I2 110.1(2) . 2 ?
N1 Cu4 I2 107.71(17) . . ?
I2 Cu4 I2 110.27(4) 2 . ?
N1 Cu4 Cu3 143.37(17) . 2 ?
I2 Cu4 Cu3 61.34(3) 2 2 ?
I2 Cu4 Cu3 108.50(3) . 2 ?
N1 Cu4 Cu3 141.2(2) . . ?
I2 Cu4 Cu3 108.50(3) 2 . ?
I2 Cu4 Cu3 61.11(3) . . ?
Cu3 Cu4 Cu3 58.25(4) 2 . ?
N1 Cu4 I1 100.5(2) . . ?
I2 Cu4 I1 112.91(4) 2 . ?
I2 Cu4 I1 114.76(4) . . ?
Cu3 Cu4 I1 58.78(3) 2 . ?
Cu3 Cu4 I1 60.16(3) . . ?
N1 Cu4 Cu4 150.7(2) . 2 ?
I2 Cu4 Cu4 59.30(3) 2 2 ?
I2 Cu4 Cu4 58.98(3) . 2 ?
Cu3 Cu4 Cu4 59.54(3) 2 2 ?
Cu3 Cu4 Cu4 59.22(3) . 2 ?
I1 Cu4 Cu4 108.776(19) . 2 ?
Cu3 I1 Cu4 60.29(3) 2 . ?
Cu3 I1 Cu3 58.60(3) 2 . ?
Cu4 I1 Cu3 59.77(3) . . ?
Cu4 I2 Cu4 61.71(3) 2 . ?
Cu4 I2 Cu3 59.67(3) 2 . ?
Cu4 I2 Cu3 59.78(3) . . ?
C2 N1 Cu4 169.1(7) . . ?
C3 N2 C1 103.9(5) . . ?
C3 N2 Cu3 125.0(4) . . ?
C1 N2 Cu3 131.0(4) . . ?
C5B N3 C5B 136(10) 2 . ?
C5A N3 C5A 125(10) 2 . ?

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
N2 C3 N2 C1 0.3(3) 4_556 . . . ?
N2 C3 N2 Cu3 176.0(5) 4_556 . . . ?
C1 C1 N2 C3 -0.9(8) 4_556 . . . ?
C2 C1 N2 C3 -179.3(6) 6_556 . . . ?
C1 C1 N2 Cu3 -176.2(5) 4_556 . . . ?
C2 C1 N2 Cu3 5.4(10) 6_556 . . . ?
C4B C5B N3 C5B -128(12) . . . 2 ?
C4A C5A N3 C5A 142(19) . . . 2 ?

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
C3 H3 I1 0.93 3.17 3.765(6) 123.5 .
C3 H3 I1 0.93 3.17 3.765(6) 123.5 4_556
C4A H4A3 I2 0.96 2.92 3.8(2) 152.0 .

_refine_diff_density_max         1.322
_refine_diff_density_min         -0.798
_refine_diff_density_rms         0.197
####################################################################### 
# 
# 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_sq
_database_code_depnum_ccdc_archive 'CCDC 1851347'
_audit_update_record             
;
2018-06-25 deposited with the CCDC.
2018-08-17 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            'C40 H56 Cu16 I16 N20 O'
_chemical_formula_weight         3880.08

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      orthorhombic
_space_group_IT_number           59
_space_group_name_H-M_alt        'P m m n'
_space_group_name_Hall           '-P 2ab 2a'

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

_cell_length_a                   17.840(2)
_cell_length_b                   31.000(4)
_cell_length_c                   8.4707(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4684.6(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7374
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      25.04

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.751
_exptl_crystal_F_000             3512
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    8.858
_shelx_estimated_absorpt_T_min   0.246
_shelx_estimated_absorpt_T_max   0.299
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29028
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.314
_diffrn_reflns_theta_max         25.135
_diffrn_reflns_theta_full        25.135
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4402
_reflns_number_gt                3723
_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       ?
_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)+(0.0349P)²+21.4821P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4402
_refine_ls_number_parameters     230
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.0880
_refine_ls_wR_factor_gt          0.0842
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.002
_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
C4 C 0.4780(7) 0.7500 0.4657(11) 0.047(3) Uani 1 2 d S T P . .
H4 H 0.4785 0.7500 0.5755 0.056 Uiso 1 2 calc R U P . .
C5 C 0.4756(4) 0.7279(2) 0.2281(8) 0.0346(15) Uani 1 1 d . . . . .
C6 C 0.7500 0.5937(3) 0.6215(12) 0.039(2) Uani 1 2 d S T P . .
H6 H 0.7500 0.6221 0.6563 0.046 Uiso 1 2 calc R U P . .
C7 C 0.3194(9) 0.6037(5) 1.1704(18) 0.135(5) Uani 1 1 d . U . . .
H7A H 0.3291 0.6325 1.2063 0.203 Uiso 1 1 calc R U . . .
H7B H 0.3595 0.5944 1.1027 0.203 Uiso 1 1 calc R U . . .
H7C H 0.3161 0.5847 1.2596 0.203 Uiso 1 1 calc R U . . .
C9 C 0.2500 0.5675(6) 0.964(2) 0.106(6) Uani 1 2 d S T P . .
H9A H 0.2062 0.5709 0.8976 0.127 Uiso 0.5 1 calc R U P . .
H9B H 0.2938 0.5709 0.8976 0.127 Uiso 0.5 1 calc R U P . .
C10 C 0.2500 0.5230(6) 1.028(2) 0.124(7) Uani 1 2 d S T P . .
H10A H 0.2061 0.5192 1.0936 0.148 Uiso 0.5 1 calc R U P . .
H10B H 0.2939 0.5192 1.0936 0.148 Uiso 0.5 1 calc R U P . .
C11 C 0.2500 0.4897(7) 0.904(2) 0.126(8) Uani 1 2 d S T P . .
H11A H 0.2060 0.4933 0.8375 0.151 Uiso 0.5 1 calc R U P . .
H11B H 0.2940 0.4933 0.8375 0.151 Uiso 0.5 1 calc R U P . .
C12 C 0.2500 0.4461(7) 0.970(2) 0.113(6) Uani 1 2 d S T P . .
H12A H 0.2062 0.4432 1.0370 0.136 Uiso 0.5 1 calc R U P . .
H12B H 0.2938 0.4432 1.0370 0.136 Uiso 0.5 1 calc R U P . .
C13 C 0.2500 0.4095(7) 0.857(2) 0.104(6) Uani 1 2 d S T P . .
H13A H 0.2940 0.4114 0.7899 0.125 Uiso 0.5 1 calc R U P . .
H13B H 0.2060 0.4114 0.7899 0.125 Uiso 0.5 1 calc R U P . .
C14 C 0.2500 0.3670(7) 0.940(4) 0.182(9) Uani 1 2 d S TU P . .
H14A H 0.2936 0.3670 1.0088 0.218 Uiso 0.5 1 calc R U P . .
H14B H 0.2064 0.3670 1.0088 0.218 Uiso 0.5 1 calc R U P . .
C16 C 0.3116(12) 0.3243(8) 0.758(3) 0.209(8) Uani 1 1 d . U . . .
H16A H 0.3040 0.3034 0.6759 0.313 Uiso 1 1 d R U . . .
H16B H 0.3507 0.3146 0.8272 0.313 Uiso 1 1 d R U . . .
H16C H 0.3258 0.3514 0.7118 0.313 Uiso 1 1 d R U . . .
Cu5 Cu 0.48834(6) 0.63905(3) 0.80485(11) 0.0483(3) Uani 1 1 d . . . . .
Cu6 Cu 0.58309(5) 0.59617(3) 0.61618(11) 0.0413(2) Uani 1 1 d . . . . .
Cu7 Cu 0.44135(5) 0.57813(3) 0.58905(12) 0.0459(2) Uani 1 1 d . . . . .
Cu8 Cu 0.48892(6) 0.65556(3) 0.48441(11) 0.0455(2) Uani 1 1 d . . . . .
I1 I 0.52524(3) 0.58794(2) 0.32290(5) 0.04190(14) Uani 1 1 d . . . . .
I2 I 0.61096(3) 0.68009(2) 0.68840(7) 0.04819(15) Uani 1 1 d . . . . .
I3 I 0.35927(3) 0.64945(2) 0.64646(7) 0.05111(16) Uani 1 1 d . . . . .
I4 I 0.51267(3) 0.55549(2) 0.85163(6) 0.04835(15) Uani 1 1 d . . . . .
N3 N 0.4776(4) 0.71377(17) 0.3817(7) 0.0432(15) Uani 1 1 d . . . . .
N4 N 0.6862(3) 0.57167(17) 0.5947(7) 0.0345(13) Uani 1 1 d . . . . .
N5 N 0.2500 0.6028(4) 1.084(2) 0.104(4) Uani 1 2 d S TU P . .
H5 H 0.2500 0.6295 1.0225 0.125 Uiso 1 2 calc R U P . .
N6 N 0.2500 0.3271(9) 0.863(3) 0.189(7) Uani 1 2 d S TU P . .
O1 O 0.2500 0.2500 0.075(2) 0.108(5) Uani 1 4 d DS T P . .
H1W H 0.2500 0.269(5) 0.003(16) 0.162 Uiso 1 2 d DS U P . .
C3 C 0.4738(4) 0.6987(2) 0.1000(8) 0.0399(17) Uani 1 1 d . . . . .
N2 N 0.4742(4) 0.6750(2) -0.0033(8) 0.0539(17) Uani 1 1 d . . . . .
C2 C 0.7111(3) 0.53184(19) 0.5481(8) 0.0305(14) Uani 1 1 d . . . . .
C1 C 0.6629(4) 0.4979(2) 0.5056(8) 0.0363(16) Uani 1 1 d . . . . .
N1 N 0.6267(3) 0.46917(19) 0.4723(8) 0.0472(16) 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
C4 N3 1.330(8) . ?
C4 N3 1.330(8) 7_575 ?
C5 C5 1.371(13) 7_575 ?
C5 N3 1.373(9) . ?
C5 C3 1.414(10) . ?
C6 N4 1.346(7) 8_755 ?
C6 N4 1.346(7) . ?
C7 N5 1.438(15) . ?
C9 C10 1.48(2) . ?
C9 N5 1.50(2) . ?
C10 C11 1.47(3) . ?
C11 C12 1.46(3) . ?
C12 C13 1.48(2) . ?
C13 C14 1.50(3) . ?
C14 N6 1.40(3) . ?
C16 N6 1.42(2) . ?
Cu5 N2 1.986(7) 1_556 ?
Cu5 I4 2.6563(11) . ?
Cu5 Cu6 2.6793(13) . ?
Cu5 I3 2.6844(12) . ?
Cu5 I2 2.7162(12) . ?
Cu5 Cu7 2.7587(13) . ?
Cu5 Cu8 2.7622(14) . ?
Cu6 N4 1.999(5) . ?
Cu6 Cu7 2.6000(13) . ?
Cu6 I4 2.6734(11) . ?
Cu6 I1 2.7022(11) . ?
Cu6 I2 2.7183(10) . ?
Cu6 Cu8 2.7308(13) . ?
Cu7 N1 1.974(6) 5_666 ?
Cu7 I4 2.6569(11) . ?
Cu7 I3 2.6961(11) . ?
Cu7 Cu8 2.6957(13) . ?
Cu7 I1 2.7230(11) . ?
Cu8 N3 2.013(6) . ?
Cu8 I1 2.5856(10) . ?
Cu8 I3 2.6963(11) . ?
Cu8 I2 2.8818(11) . ?
N4 C2 1.370(8) . ?
N5 C7 1.438(15) 8_655 ?
N6 C16 1.42(2) 8_655 ?
C3 N2 1.142(9) . ?
N2 Cu5 1.986(7) 1_554 ?
C2 C2 1.387(12) 8_755 ?
C2 C1 1.405(9) . ?
C1 N1 1.136(8) . ?
N1 Cu7 1.974(6) 5_666 ?

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
N3 C4 N3 115.3(9) . 7_575 ?
C5 C5 N3 108.6(4) 7_575 . ?
C5 C5 C3 129.8(4) 7_575 . ?
N3 C5 C3 121.6(6) . . ?
N4 C6 N4 115.5(8) 8_755 . ?
C10 C9 N5 115.8(16) . . ?
C9 C10 C11 113.2(16) . . ?
C12 C11 C10 112.0(16) . . ?
C11 C12 C13 117.3(18) . . ?
C12 C13 C14 111.6(19) . . ?
N6 C14 C13 124(3) . . ?
N2 Cu5 I4 116.4(2) 1_556 . ?
N2 Cu5 Cu6 147.8(2) 1_556 . ?
I4 Cu5 Cu6 60.14(3) . . ?
N2 Cu5 I3 103.4(2) 1_556 . ?
I4 Cu5 I3 109.38(4) . . ?
Cu6 Cu5 I3 107.62(4) . . ?
N2 Cu5 I2 97.9(2) 1_556 . ?
I4 Cu5 I2 112.29(4) . . ?
Cu6 Cu5 I2 60.50(3) . . ?
I3 Cu5 I2 116.94(4) . . ?
N2 Cu5 Cu7 152.5(2) 1_556 . ?
I4 Cu5 Cu7 58.73(3) . . ?
Cu6 Cu5 Cu7 57.10(3) . . ?
I3 Cu5 Cu7 59.36(3) . . ?
I2 Cu5 Cu7 108.95(4) . . ?
N2 Cu5 Cu8 134.5(2) 1_556 . ?
I4 Cu5 Cu8 109.07(4) . . ?
Cu6 Cu5 Cu8 60.22(3) . . ?
I3 Cu5 Cu8 59.32(3) . . ?
I2 Cu5 Cu8 63.47(3) . . ?
Cu7 Cu5 Cu8 58.45(3) . . ?
N4 Cu6 Cu7 143.65(16) . . ?
N4 Cu6 I4 108.74(17) . . ?
Cu7 Cu6 I4 60.49(3) . . ?
N4 Cu6 Cu5 145.46(17) . . ?
Cu7 Cu6 Cu5 62.99(4) . . ?
I4 Cu6 Cu5 59.51(3) . . ?
N4 Cu6 I1 103.41(17) . . ?
Cu7 Cu6 I1 61.77(3) . . ?
I4 Cu6 I1 117.50(4) . . ?
Cu5 Cu6 I1 110.75(4) . . ?
N4 Cu6 I2 102.47(15) . . ?
Cu7 Cu6 I2 113.81(4) . . ?
I4 Cu6 I2 111.69(4) . . ?
Cu5 Cu6 I2 60.42(3) . . ?
I1 Cu6 I2 111.54(4) . . ?
N4 Cu6 Cu8 141.74(17) . . ?
Cu7 Cu6 Cu8 60.69(4) . . ?
I4 Cu6 Cu8 109.50(4) . . ?
Cu5 Cu6 Cu8 61.39(4) . . ?
I1 Cu6 Cu8 56.83(3) . . ?
I2 Cu6 Cu8 63.85(3) . . ?
N1 Cu7 Cu6 141.40(18) 5_666 . ?
N1 Cu7 I4 108.6(2) 5_666 . ?
Cu6 Cu7 I4 61.12(3) . . ?
N1 Cu7 I3 108.82(18) 5_666 . ?
Cu6 Cu7 I3 109.63(4) . . ?
I4 Cu7 I3 109.01(4) . . ?
N1 Cu7 Cu8 140.2(2) 5_666 . ?
Cu6 Cu7 Cu8 62.05(3) . . ?
I4 Cu7 Cu8 111.08(4) . . ?
I3 Cu7 Cu8 60.01(3) . . ?
N1 Cu7 I1 101.7(2) 5_666 . ?
Cu6 Cu7 I1 60.96(3) . . ?
I4 Cu7 I1 117.35(4) . . ?
I3 Cu7 I1 110.87(4) . . ?
Cu8 Cu7 I1 57.00(3) . . ?
N1 Cu7 Cu5 150.5(2) 5_666 . ?
Cu6 Cu7 Cu5 59.91(3) . . ?
I4 Cu7 Cu5 58.71(3) . . ?
I3 Cu7 Cu5 58.95(3) . . ?
Cu8 Cu7 Cu5 60.84(4) . . ?
I1 Cu7 Cu5 107.77(4) . . ?
N3 Cu8 I1 121.53(17) . . ?
N3 Cu8 I3 101.36(19) . . ?
I1 Cu8 I3 115.30(4) . . ?
N3 Cu8 Cu7 155.3(2) . . ?
I1 Cu8 Cu7 62.03(3) . . ?
I3 Cu8 Cu7 60.00(3) . . ?
N3 Cu8 Cu6 147.4(2) . . ?
I1 Cu8 Cu6 61.03(3) . . ?
I3 Cu8 Cu6 105.81(4) . . ?
Cu7 Cu8 Cu6 57.25(3) . . ?
N3 Cu8 Cu5 126.18(17) . . ?
I1 Cu8 Cu5 111.76(4) . . ?
I3 Cu8 Cu5 58.90(3) . . ?
Cu7 Cu8 Cu5 60.71(3) . . ?
Cu6 Cu8 Cu5 58.39(3) . . ?
N3 Cu8 I2 95.64(18) . . ?
I1 Cu8 I2 109.99(4) . . ?
I3 Cu8 I2 111.19(4) . . ?
Cu7 Cu8 I2 106.00(4) . . ?
Cu6 Cu8 I2 57.86(3) . . ?
Cu5 Cu8 I2 57.49(3) . . ?
Cu8 I1 Cu6 62.14(3) . . ?
Cu8 I1 Cu7 60.97(3) . . ?
Cu6 I1 Cu7 57.27(3) . . ?
Cu5 I2 Cu6 59.08(3) . . ?
Cu5 I2 Cu8 59.04(3) . . ?
Cu6 I2 Cu8 58.28(3) . . ?
Cu5 I3 Cu7 61.69(3) . . ?
Cu5 I3 Cu8 61.77(3) . . ?
Cu7 I3 Cu8 59.99(3) . . ?
Cu5 I4 Cu7 62.56(3) . . ?
Cu5 I4 Cu6 60.36(3) . . ?
Cu7 I4 Cu6 58.39(3) . . ?
C4 N3 C5 103.8(6) . . ?
C4 N3 Cu8 121.7(5) . . ?
C5 N3 Cu8 134.2(5) . . ?
C6 N4 C2 103.3(6) . . ?
C6 N4 Cu6 124.8(5) . . ?
C2 N4 Cu6 131.8(4) . . ?
C7 N5 C7 119.0(18) . 8_655 ?
C7 N5 C9 111.1(9) . . ?
C7 N5 C9 111.1(9) 8_655 . ?
C16 N6 C16 102(3) 8_655 . ?
C16 N6 C14 110.4(19) 8_655 . ?
C16 N6 C14 110.4(19) . . ?
N2 C3 C5 178.4(9) . . ?
C3 N2 Cu5 171.0(7) . 1_554 ?
N4 C2 C2 108.9(3) . 8_755 ?
N4 C2 C1 123.3(6) . . ?
C2 C2 C1 127.8(4) 8_755 . ?
N1 C1 C2 176.7(7) . . ?
C1 N1 Cu7 176.3(6) . 5_666 ?

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
N5 C9 C10 C11 180.000(12) . . . . ?
C9 C10 C11 C12 180.000(11) . . . . ?
C10 C11 C12 C13 180.000(10) . . . . ?
C11 C12 C13 C14 180.000(13) . . . . ?
C12 C13 C14 N6 180.000(12) . . . . ?
N3 C4 N3 C5 -1.0(13) 7_575 . . . ?
N3 C4 N3 Cu8 173.5(5) 7_575 . . . ?
C5 C5 N3 C4 0.6(8) 7_575 . . . ?
C3 C5 N3 C4 -179.4(8) . . . . ?
C5 C5 N3 Cu8 -172.9(5) 7_575 . . . ?
C3 C5 N3 Cu8 7.1(11) . . . . ?
N4 C6 N4 C2 0.7(12) 8_755 . . . ?
N4 C6 N4 Cu6 -177.6(4) 8_755 . . . ?
C10 C9 N5 C7 67.4(11) . . . . ?
C10 C9 N5 C7 -67.4(11) . . . 8_655 ?
C13 C14 N6 C16 -55.9(18) . . . 8_655 ?
C13 C14 N6 C16 55.9(18) . . . . ?
C6 N4 C2 C2 -0.4(7) . . . 8_755 ?
Cu6 N4 C2 C2 177.8(4) . . . 8_755 ?
C6 N4 C2 C1 -179.3(8) . . . . ?
Cu6 N4 C2 C1 -1.1(11) . . . . ?

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
C6 H6 I2 0.93 3.08 3.695(7) 125.6 .
C6 H6 I2 0.93 3.08 3.695(7) 125.6 8_755
C16 H16C I1 0.96 3.27 4.04(2) 138.8 5_666
O1 H1W N6 0.84(2) 2.17(6) 2.99(3) 167(19) 1_554

_refine_diff_density_max         1.709
_refine_diff_density_min         -0.934
_refine_diff_density_rms         0.153
####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1851346'
_audit_update_record             
;
2018-06-25 deposited with the CCDC.
2018-08-17 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            'C14 H23 Cu4 I4 N5'
_chemical_formula_weight         1023.13

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           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                   11.3646(11)
_cell_length_b                   14.8491(12)
_cell_length_c                   14.7153(13)
_cell_angle_alpha                90
_cell_angle_beta                 98.850(2)
_cell_angle_gamma                90
_cell_volume                     2453.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6947
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      25.21

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.770
_exptl_crystal_F_000             1880
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    8.463
_shelx_estimated_absorpt_T_min   0.258
_shelx_estimated_absorpt_T_max   0.311
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15126
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.960
_diffrn_reflns_theta_max         25.267
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             4369
_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.
 
 _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)+(0.0256P)²+28.7936P] 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_number_reflns         4369
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0849
_refine_ls_wR_factor_gt          0.0830
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
C1 C 0.7613(6) 0.7477(5) 0.6971(5) 0.0249(16) Uani 1 1 d . . . . .
H1 H 0.7544 0.7414 0.7589 0.030 Uiso 1 1 calc R U . . .
C2 C 0.2816(7) 1.1376(5) 0.5127(5) 0.0264(16) Uani 1 1 d . . . . .
C3 C 0.2515(6) 1.1965(5) 0.4374(5) 0.0226(15) Uani 1 1 d . . . . .
C4 C 0.3500(6) 0.8250(5) 0.9924(5) 0.0226(15) Uani 1 1 d . . . . .
C5 C 0.3069(6) 0.7791(5) 1.0657(5) 0.0209(15) Uani 1 1 d . . . . .
C6 C 0.5115(8) 0.5939(6) 0.6901(6) 0.039(2) Uani 1 1 d . . . . .
H6A H 0.5830 0.5579 0.6915 0.046 Uiso 1 1 calc R U . . .
H6B H 0.5357 0.6549 0.7074 0.046 Uiso 1 1 calc R U . . .
C7 C 0.4438(9) 0.5944(7) 0.5932(7) 0.051(3) Uani 1 1 d . . . . .
H7A H 0.4294 0.5330 0.5720 0.061 Uiso 1 1 calc R U . . .
H7B H 0.3673 0.6236 0.5927 0.061 Uiso 1 1 calc R U . . .
C8 C 0.5128(10) 0.6432(8) 0.5299(7) 0.058(3) Uani 1 1 d . . . . .
H8A H 0.5334 0.7022 0.5540 0.087 Uiso 1 1 calc R U . . .
H8B H 0.4653 0.6485 0.4703 0.087 Uiso 1 1 calc R U . . .
H8C H 0.5842 0.6103 0.5248 0.087 Uiso 1 1 calc R U . . .
C9 C 0.5027(9) 0.5630(7) 0.8576(7) 0.050(2) Uani 1 1 d . . . . .
H9A H 0.4549 0.5331 0.8978 0.060 Uiso 1 1 calc R U . . .
H9B H 0.5783 0.5316 0.8626 0.060 Uiso 1 1 calc R U . . .
C10 C 0.5246(10) 0.6575(7) 0.8891(7) 0.055(3) Uani 1 1 d . . . . .
H10A H 0.4508 0.6913 0.8772 0.066 Uiso 1 1 calc R U . . .
H10B H 0.5812 0.6853 0.8547 0.066 Uiso 1 1 calc R U . . .
C11 C 0.5735(10) 0.6608(8) 0.9919(7) 0.061(3) Uani 1 1 d . . . . .
H11A H 0.5122 0.6434 1.0266 0.092 Uiso 1 1 calc R U . . .
H11B H 0.5993 0.7210 1.0086 0.092 Uiso 1 1 calc R U . . .
H11C H 0.6397 0.6203 1.0051 0.092 Uiso 1 1 calc R U . . .
C12 C 0.3958(8) 0.4612(6) 0.7375(8) 0.049(2) Uani 1 1 d . . . . .
H12A H 0.3463 0.4434 0.7826 0.059 Uiso 1 1 calc R U . . .
H12B H 0.3458 0.4613 0.6778 0.059 Uiso 1 1 calc R U . . .
C13 C 0.4899(9) 0.3925(7) 0.7364(7) 0.050(2) Uani 1 1 d . . . . .
H13A H 0.5335 0.3844 0.7979 0.059 Uiso 1 1 calc R U . . .
H13B H 0.5455 0.4118 0.6965 0.059 Uiso 1 1 calc R U . . .
C14 C 0.4308(11) 0.3039(6) 0.7013(9) 0.064(3) Uani 1 1 d . . . . .
H14A H 0.3766 0.2850 0.7416 0.096 Uiso 1 1 calc R U . . .
H14B H 0.4907 0.2586 0.6998 0.096 Uiso 1 1 calc R U . . .
H14C H 0.3878 0.3126 0.6405 0.096 Uiso 1 1 calc R U . . .
Cu1 Cu 0.61820(10) 0.91612(7) 0.69700(7) 0.0374(3) Uani 1 1 d . . . . .
Cu2 Cu 0.41722(10) 1.02571(7) 0.67300(7) 0.0361(2) Uani 1 1 d . . . . .
Cu3 Cu 0.60821(10) 1.07051(6) 0.79602(7) 0.0336(2) Uani 1 1 d . . . . .
Cu4 Cu 0.45932(10) 0.92570(7) 0.83694(7) 0.0386(3) Uani 1 1 d . . . . .
I1 I 0.62746(5) 1.07354(3) 0.61735(3) 0.03169(14) Uani 1 1 d . . . . .
I2 I 0.69505(5) 0.92192(4) 0.88243(3) 0.03150(14) Uani 1 1 d . . . . .
I3 I 0.37969(4) 1.09533(3) 0.83426(3) 0.02810(13) Uani 1 1 d . . . . .
I4 I 0.38967(5) 0.84789(3) 0.67332(4) 0.03039(13) Uani 1 1 d . . . . .
N1 N 0.3086(7) 1.0911(4) 0.5749(5) 0.0372(17) Uani 1 1 d . . . . .
N2 N 0.3852(6) 0.8596(4) 0.9319(4) 0.0293(14) Uani 1 1 d . . . . .
N3 N 0.7190(5) 0.8193(4) 0.6483(4) 0.0216(13) Uani 1 1 d . . . . .
N4 N 0.6860(5) 1.1856(4) 0.8481(4) 0.0219(13) Uani 1 1 d . . . . .
N5 N 0.4395(6) 0.5569(5) 0.7592(5) 0.0373(17) Uani 1 1 d . . . . .
H5 H 0.3683 0.5948 0.7555 0.045 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
C1 N3 1.331(9) . ?
C1 N4 1.332(9) 2_646 ?
C2 N1 1.150(10) . ?
C2 C3 1.412(10) . ?
C3 N3 1.374(9) 3_676 ?
C3 C5 1.391(10) 2_556 ?
C4 N2 1.153(9) . ?
C4 C5 1.425(10) . ?
C5 N4 1.363(9) 3_677 ?
C5 C3 1.391(10) 2_546 ?
C6 N5 1.504(11) . ?
C6 C7 1.513(13) . ?
C7 C8 1.494(14) . ?
C9 C10 1.485(14) . ?
C9 N5 1.518(12) . ?
C10 C11 1.531(14) . ?
C12 C13 1.480(12) . ?
C12 N5 1.523(11) . ?
C13 C14 1.531(14) . ?
Cu1 N3 2.036(6) . ?
Cu1 I1 2.6243(11) . ?
Cu1 Cu3 2.7282(14) . ?
Cu1 I2 2.7355(12) . ?
Cu1 I4 2.7595(13) . ?
Cu1 Cu2 2.7824(15) . ?
Cu1 Cu4 2.9438(15) . ?
Cu2 N1 2.001(7) . ?
Cu2 I4 2.6590(12) . ?
Cu2 I3 2.6820(12) . ?
Cu2 Cu3 2.6874(15) . ?
Cu2 I1 2.7360(12) . ?
Cu2 Cu4 2.8105(14) . ?
Cu3 N4 2.021(6) . ?
Cu3 I2 2.6594(12) . ?
Cu3 I1 2.6720(11) . ?
Cu3 I3 2.7653(12) . ?
Cu3 Cu4 2.8571(14) . ?
Cu4 N2 1.996(6) . ?
Cu4 I2 2.6602(13) . ?
Cu4 I3 2.6747(12) . ?
Cu4 I4 2.6782(12) . ?
N3 C3 1.374(9) 3_676 ?
N4 C1 1.332(9) 2_656 ?
N4 C5 1.363(9) 3_677 ?

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
N3 C1 N4 115.9(6) . 2_646 ?
N1 C2 C3 178.2(9) . . ?
N3 C3 C5 107.6(6) 3_676 2_556 ?
N3 C3 C2 123.4(7) 3_676 . ?
C5 C3 C2 128.9(7) 2_556 . ?
N2 C4 C5 177.9(8) . . ?
N4 C5 C3 109.2(6) 3_677 2_546 ?
N4 C5 C4 122.8(6) 3_677 . ?
C3 C5 C4 127.9(6) 2_546 . ?
N5 C6 C7 112.9(7) . . ?
C8 C7 C6 110.5(8) . . ?
C10 C9 N5 112.7(8) . . ?
C9 C10 C11 110.9(9) . . ?
C13 C12 N5 115.6(8) . . ?
C12 C13 C14 108.4(9) . . ?
N3 Cu1 I1 114.10(17) . . ?
N3 Cu1 Cu3 148.59(18) . . ?
I1 Cu1 Cu3 59.86(3) . . ?
N3 Cu1 I2 105.25(17) . . ?
I1 Cu1 I2 112.88(4) . . ?
Cu3 Cu1 I2 58.25(3) . . ?
N3 Cu1 I4 105.40(18) . . ?
I1 Cu1 I4 111.86(4) . . ?
Cu3 Cu1 I4 105.09(4) . . ?
I2 Cu1 I4 106.70(4) . . ?
N3 Cu1 Cu2 149.71(18) . . ?
I1 Cu1 Cu2 60.72(3) . . ?
Cu3 Cu1 Cu2 58.37(4) . . ?
I2 Cu1 Cu2 103.77(4) . . ?
I4 Cu1 Cu2 57.34(3) . . ?
N3 Cu1 Cu4 135.99(17) . . ?
I1 Cu1 Cu4 109.90(4) . . ?
Cu3 Cu1 Cu4 60.35(4) . . ?
I2 Cu1 Cu4 55.72(3) . . ?
I4 Cu1 Cu4 55.90(3) . . ?
Cu2 Cu1 Cu4 58.71(4) . . ?
N1 Cu2 I4 115.1(2) . . ?
N1 Cu2 I3 106.67(19) . . ?
I4 Cu2 I3 110.27(4) . . ?
N1 Cu2 Cu3 135.3(2) . . ?
I4 Cu2 Cu3 109.13(4) . . ?
I3 Cu2 Cu3 62.00(3) . . ?
N1 Cu2 I1 97.4(2) . . ?
I4 Cu2 I1 111.52(4) . . ?
I3 Cu2 I1 115.45(4) . . ?
Cu3 Cu2 I1 59.02(3) . . ?
N1 Cu2 Cu1 141.1(2) . . ?
I4 Cu2 Cu1 60.89(3) . . ?
I3 Cu2 Cu1 110.63(4) . . ?
Cu3 Cu2 Cu1 59.81(4) . . ?
I1 Cu2 Cu1 56.78(3) . . ?
N1 Cu2 Cu4 151.7(2) . . ?
I4 Cu2 Cu4 58.56(3) . . ?
I3 Cu2 Cu4 58.23(3) . . ?
Cu3 Cu2 Cu4 62.57(4) . . ?
I1 Cu2 Cu4 110.66(4) . . ?
Cu1 Cu2 Cu4 63.51(4) . . ?
N4 Cu3 I2 114.32(18) . . ?
N4 Cu3 I1 105.19(17) . . ?
I2 Cu3 I1 113.82(4) . . ?
N4 Cu3 Cu2 136.55(18) . . ?
I2 Cu3 Cu2 108.58(4) . . ?
I1 Cu3 Cu2 61.40(3) . . ?
N4 Cu3 Cu1 149.53(18) . . ?
I2 Cu3 Cu1 61.01(3) . . ?
I1 Cu3 Cu1 58.14(3) . . ?
Cu2 Cu3 Cu1 61.83(4) . . ?
N4 Cu3 I3 100.35(17) . . ?
I2 Cu3 I3 107.72(4) . . ?
I1 Cu3 I3 114.81(4) . . ?
Cu2 Cu3 I3 58.91(3) . . ?
Cu1 Cu3 I3 109.77(4) . . ?
N4 Cu3 Cu4 142.69(17) . . ?
I2 Cu3 Cu4 57.53(3) . . ?
I1 Cu3 Cu4 111.15(4) . . ?
Cu2 Cu3 Cu4 60.82(4) . . ?
Cu1 Cu3 Cu4 63.57(4) . . ?
I3 Cu3 Cu4 56.78(3) . . ?
N2 Cu4 I2 109.3(2) . . ?
N2 Cu4 I3 107.14(19) . . ?
I2 Cu4 I3 110.42(4) . . ?
N2 Cu4 I4 108.60(19) . . ?
I2 Cu4 I4 111.35(4) . . ?
I3 Cu4 I4 109.91(4) . . ?
N2 Cu4 Cu2 145.7(2) . . ?
I2 Cu4 Cu2 105.01(4) . . ?
I3 Cu4 Cu2 58.48(3) . . ?
I4 Cu4 Cu2 57.89(3) . . ?
N2 Cu4 Cu3 147.6(2) . . ?
I2 Cu4 Cu3 57.50(3) . . ?
I3 Cu4 Cu3 59.88(3) . . ?
I4 Cu4 Cu3 103.76(4) . . ?
Cu2 Cu4 Cu3 56.60(4) . . ?
N2 Cu4 Cu1 146.73(19) . . ?
I2 Cu4 Cu1 58.17(3) . . ?
I3 Cu4 Cu1 106.13(4) . . ?
I4 Cu4 Cu1 58.56(3) . . ?
Cu2 Cu4 Cu1 57.78(4) . . ?
Cu3 Cu4 Cu1 56.08(3) . . ?
Cu1 I1 Cu3 62.00(3) . . ?
Cu1 I1 Cu2 62.50(3) . . ?
Cu3 I1 Cu2 59.58(3) . . ?
Cu3 I2 Cu4 64.97(3) . . ?
Cu3 I2 Cu1 60.74(3) . . ?
Cu4 I2 Cu1 66.11(3) . . ?
Cu4 I3 Cu2 63.29(3) . . ?
Cu4 I3 Cu3 63.34(3) . . ?
Cu2 I3 Cu3 59.10(3) . . ?
Cu2 I4 Cu4 63.55(3) . . ?
Cu2 I4 Cu1 61.76(3) . . ?
Cu4 I4 Cu1 65.53(3) . . ?
C2 N1 Cu2 157.7(8) . . ?
C4 N2 Cu4 173.9(6) . . ?
C1 N3 C3 103.9(6) . 3_676 ?
C1 N3 Cu1 123.4(5) . . ?
C3 N3 Cu1 132.4(5) 3_676 . ?
C1 N4 C5 103.4(6) 2_656 3_677 ?
C1 N4 Cu3 126.9(5) 2_656 . ?
C5 N4 Cu3 129.7(5) 3_677 . ?
C6 N5 C9 113.4(7) . . ?
C6 N5 C12 113.1(7) . . ?
C9 N5 C12 110.3(7) . . ?

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
N5 C6 C7 C8 172.2(8) . . . . ?
N5 C9 C10 C11 172.6(9) . . . . ?
N5 C12 C13 C14 -172.6(9) . . . . ?
N4 C1 N3 C3 -1.0(9) 2_646 . . 3_676 ?
N4 C1 N3 Cu1 172.7(5) 2_646 . . . ?
C7 C6 N5 C9 -175.3(8) . . . . ?
C7 C6 N5 C12 58.1(10) . . . . ?
C10 C9 N5 C6 64.1(10) . . . . ?
C10 C9 N5 C12 -167.9(8) . . . . ?
C13 C12 N5 C6 61.6(12) . . . . ?
C13 C12 N5 C9 -66.6(11) . . . . ?

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
C1 H1 I1 0.93 3.25 3.832(7) 122.4 2_646
C6 H6B I4 0.97 3.31 4.012(9) 130.8 .
C7 H7B I3 0.97 3.18 3.983(10) 140.7 2_546
C12 H12A I4 0.97 3.19 4.048(9) 148.7 2_546
C12 H12B I3 0.97 3.23 3.724(9) 113.6 2_546
N5 H5 I3 0.98 2.92 3.720(7) 139.2 2_546

_refine_diff_density_max         1.390
_refine_diff_density_min         -0.848
_refine_diff_density_rms         0.169
