# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_Compound110
_database_code_depnum_ccdc_archive 'CCDC 1517062'
_audit_update_record             
;
2018-12-03 deposited with the CCDC.
2018-12-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H42 Cu3 I6 N6 O8'
_chemical_formula_weight         1662.79

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'
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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

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

_cell_length_a                   14.504(4)
_cell_length_b                   24.027(6)
_cell_length_c                   10.129(3)
_cell_angle_alpha                90
_cell_angle_beta                 133.170(2)
_cell_angle_gamma                90
_cell_volume                     2574.2(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7468
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      28.19

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.145
_exptl_crystal_F_000             1562
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    4.876
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.391
_exptl_absorpt_correction_T_max  0.458
_exptl_absorpt_process_details   'multi-scan absorption correction'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Duo Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19903
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.182
_diffrn_reflns_theta_max         28.490
_diffrn_reflns_theta_full        25.242
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3338
_reflns_number_gt                2353
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3338
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1592
_refine_ls_wR_factor_gt          0.1364
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
I2 I 0.500000 0.15834(2) 0.000000 0.0370(2) Uani 1 2 d S T P . .
I1 I 0.39637(5) 0.16110(2) 0.16599(7) 0.0509(2) Uani 1 1 d . . . . .
Cu1 Cu 0.59530(8) 0.500000 0.23020(11) 0.0180(2) Uani 1 2 d S T P . .
Cu2 Cu 0.500000 0.500000 0.500000 0.0343(4) Uani 1 4 d S T P . .
O4 O 0.7746(4) 0.500000 0.4650(7) 0.0209(11) Uani 1 2 d S T P . .
O1 O 0.4113(5) 0.500000 0.0179(7) 0.0209(10) Uani 1 2 d S T P . .
O2 O 0.3748(5) 0.500000 0.1983(7) 0.0275(12) Uani 1 2 d S T P . .
O3 O 0.6616(5) 0.500000 0.5358(7) 0.0307(13) Uani 1 2 d S T P . .
N2 N 0.500000 0.4066(2) 0.500000 0.0214(13) Uani 1 2 d S T P . .
N1 N 0.6026(4) 0.41426(18) 0.2376(5) 0.0207(9) Uani 1 1 d . . . . .
C1 C 0.5025(5) 0.3819(2) 0.1660(7) 0.0243(11) Uani 1 1 d . . . . .
H1 H 0.424785 0.398913 0.104549 0.029 Uiso 1 1 calc R U . . .
C2 C 0.5089(6) 0.3243(2) 0.1789(8) 0.0306(13) Uani 1 1 d . . . . .
H2 H 0.437168 0.303063 0.125368 0.037 Uiso 1 1 calc R U . . .
C5 C 0.7137(5) 0.3887(2) 0.3251(7) 0.0274(12) Uani 1 1 d . . . . .
H5 H 0.783857 0.410383 0.372998 0.033 Uiso 1 1 calc R U . . .
C9 C 0.3363(7) 0.500000 0.0450(9) 0.0180(14) Uani 1 2 d S T P . .
C6 C 0.3921(5) 0.3783(2) 0.3848(7) 0.0268(12) Uani 1 1 d . . . . .
H6 H 0.316872 0.398143 0.304464 0.032 Uiso 1 1 calc R U . . .
C11 C 0.7675(7) 0.500000 0.5826(10) 0.0194(15) Uani 1 2 d S T P . .
C10 C 0.1976(7) 0.500000 -0.1209(10) 0.0304(18) Uani 1 2 d S T P . .
H10A H 0.164401 0.463145 -0.141846 0.046 Uiso 0.5 1 calc R U P . .
H10B H 0.184597 0.511680 -0.223326 0.046 Uiso 0.5 1 calc R U P . .
H10C H 0.155032 0.525175 -0.104042 0.046 Uiso 0.5 1 calc R U P . .
C3 C 0.6259(6) 0.2995(2) 0.2744(8) 0.0352(14) Uani 1 1 d . . . . .
H3 H 0.633861 0.261068 0.288369 0.042 Uiso 1 1 calc R U . . .
C8 C 0.500000 0.2904(4) 0.500000 0.039(2) Uani 1 2 d S T P . .
H8 H 0.499998 0.251663 0.499999 0.047 Uiso 1 2 calc R U P . .
C12 C 0.8866(7) 0.500000 0.7763(10) 0.0327(19) Uani 1 2 d S T P . .
H12A H 0.914329 0.462367 0.816677 0.049 Uiso 0.5 1 calc R U P . .
H12B H 0.872390 0.517377 0.846362 0.049 Uiso 0.5 1 calc R U P . .
H12C H 0.950307 0.520256 0.791212 0.049 Uiso 0.5 1 calc R U P . .
C7 C 0.3867(6) 0.3200(2) 0.3789(8) 0.0314(13) Uani 1 1 d . . . . .
H7 H 0.309725 0.301496 0.296548 0.038 Uiso 1 1 calc R U . . .
C4 C 0.7284(6) 0.3311(2) 0.3472(9) 0.0363(14) Uani 1 1 d . . . . .
H4 H 0.807024 0.314739 0.410687 0.044 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
I2 I1 2.9236(7) . ?
I2 I1 2.9236(7) 2_655 ?
Cu1 O1 1.973(5) . ?
Cu1 O4 1.989(5) . ?
Cu1 N1 2.062(4) 6_565 ?
Cu1 N1 2.062(4) . ?
Cu2 O3 2.112(5) 5_666 ?
Cu2 O3 2.112(5) . ?
Cu2 N2 2.244(6) 5_666 ?
Cu2 N2 2.244(6) . ?
Cu2 O2 2.246(5) 5_666 ?
Cu2 O2 2.246(5) . ?
O4 C11 1.264(8) . ?
O1 C9 1.292(8) . ?
O2 C9 1.239(9) . ?
O3 C11 1.261(8) . ?
N2 C6 1.332(6) 2_656 ?
N2 C6 1.332(6) . ?
N1 C1 1.341(7) . ?
N1 C5 1.343(6) . ?
C1 C2 1.386(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.387(9) . ?
C2 H2 0.9300 . ?
C5 C4 1.396(8) . ?
C5 H5 0.9300 . ?
C9 C10 1.498(10) . ?
C6 C7 1.403(8) . ?
C6 H6 0.9300 . ?
C11 C12 1.481(10) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C10 H10A 0.96(3) 6_565 ?
C10 H10B 0.96(4) 6_565 ?
C10 H10C 0.96(6) 6_565 ?
C3 C4 1.353(9) . ?
C3 H3 0.9300 . ?
C8 C7 1.398(7) 2_656 ?
C8 C7 1.398(7) . ?
C8 H8 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C12 H12A 0.960(5) 6_565 ?
C12 H12B 0.96(4) 6_565 ?
C12 H12C 0.96(5) 6_565 ?
C7 H7 0.9300 . ?
C4 H4 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
I1 I2 I1 177.41(2) . 2_655 ?
O1 Cu1 O4 172.0(2) . . ?
O1 Cu1 N1 92.14(12) . 6_565 ?
O4 Cu1 N1 87.92(12) . 6_565 ?
O1 Cu1 N1 92.14(12) . . ?
O4 Cu1 N1 87.92(12) . . ?
N1 Cu1 N1 175.7(2) 6_565 . ?
O3 Cu2 O3 180.0(3) 5_666 . ?
O3 Cu2 N2 90.000(1) 5_666 5_666 ?
O3 Cu2 N2 90.000(1) . 5_666 ?
O3 Cu2 N2 90.000(1) 5_666 . ?
O3 Cu2 N2 90.000(1) . . ?
N2 Cu2 N2 180.0 5_666 . ?
O3 Cu2 O2 90.15(19) 5_666 5_666 ?
O3 Cu2 O2 89.85(19) . 5_666 ?
N2 Cu2 O2 90.000(1) 5_666 5_666 ?
N2 Cu2 O2 90.000(1) . 5_666 ?
O3 Cu2 O2 89.85(19) 5_666 . ?
O3 Cu2 O2 90.15(19) . . ?
N2 Cu2 O2 90.000(1) 5_666 . ?
N2 Cu2 O2 90.000(1) . . ?
O2 Cu2 O2 180.0(3) 5_666 . ?
C11 O4 Cu1 104.1(4) . . ?
C9 O1 Cu1 118.4(4) . . ?
C9 O2 Cu2 163.1(5) . . ?
C11 O3 Cu2 171.2(5) . . ?
C6 N2 C6 118.6(7) 2_656 . ?
C6 N2 Cu2 120.7(3) 2_656 . ?
C6 N2 Cu2 120.7(3) . . ?
C1 N1 C5 117.3(5) . . ?
C1 N1 Cu1 123.4(4) . . ?
C5 N1 Cu1 119.3(3) . . ?
N1 C1 C2 123.4(5) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C1 C2 C3 117.7(5) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
N1 C5 C4 122.8(5) . . ?
N1 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
O2 C9 O1 122.9(7) . . ?
O2 C9 C10 121.0(6) . . ?
O1 C9 C10 116.1(6) . . ?
N2 C6 C7 123.0(5) . . ?
N2 C6 H6 118.5 . . ?
C7 C6 H6 118.5 . . ?
O3 C11 O4 120.6(7) . . ?
O3 C11 C12 121.0(7) . . ?
O4 C11 C12 118.3(7) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C10 H10A 109.5(5) . 6_565 ?
H10A C10 H10A 134.6 . 6_565 ?
H10B C10 H10A 78.1 . 6_565 ?
H10C C10 H10A 34.0 . 6_565 ?
C9 C10 H10B 109.5(9) . 6_565 ?
H10A C10 H10B 78.1 . 6_565 ?
H10B C10 H10B 34.0 . 6_565 ?
H10C C10 H10B 134.6 . 6_565 ?
H10A C10 H10B 109.5 6_565 6_565 ?
C9 C10 H10C 109.5(13) . 6_565 ?
H10A C10 H10C 34.0 . 6_565 ?
H10B C10 H10C 134.6 . 6_565 ?
H10C C10 H10C 78.1 . 6_565 ?
H10A C10 H10C 109.5 6_565 6_565 ?
H10B C10 H10C 109.5 6_565 6_565 ?
C4 C3 C2 120.2(5) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C7 C8 C7 118.8(8) 2_656 . ?
C7 C8 H8 120.6 2_656 . ?
C7 C8 H8 120.6 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C12 H12A 109.47(10) . 6_565 ?
H12A C12 H12A 140.7 . 6_565 ?
H12B C12 H12A 60.9 . 6_565 ?
H12C C12 H12A 51.6 . 6_565 ?
C11 C12 H12B 109.5(10) . 6_565 ?
H12A C12 H12B 60.9 . 6_565 ?
H12B C12 H12B 51.6 . 6_565 ?
H12C C12 H12B 140.7 . 6_565 ?
H12A C12 H12B 109.5 6_565 6_565 ?
C11 C12 H12C 109.5(11) . 6_565 ?
H12A C12 H12C 51.6 . 6_565 ?
H12B C12 H12C 140.7 . 6_565 ?
H12C C12 H12C 60.9 . 6_565 ?
H12A C12 H12C 109.5 6_565 6_565 ?
H12B C12 H12C 109.5 6_565 6_565 ?
C8 C7 C6 118.2(6) . . ?
C8 C7 H7 120.9 . . ?
C6 C7 H7 120.9 . . ?
C3 C4 C5 118.6(6) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?

_refine_diff_density_max         0.865
_refine_diff_density_min         -2.561
_refine_diff_density_rms         0.174


_exptl_crystal_preparation       'Magnetic properties,Biological activity'
