# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1832729'
_audit_update_record             
;
2018-12-13 deposited with the CCDC.
2018-12-13 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            'C46 H38 Cu N8 O14'
_chemical_formula_weight         990.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/n'
_space_group_name_Hall           '-P 2yac'

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

_cell_length_a                   15.8566(6)
_cell_length_b                   7.8896(3)
_cell_length_c                   17.8929(7)
_cell_angle_alpha                90
_cell_angle_beta                 106.5390(10)
_cell_angle_gamma                90
_cell_volume                     2145.83(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9076
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      26.41

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_F_000             1022
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.23
_exptl_absorpt_coefficient_mu    0.591
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7921
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Photon 100 CMOS detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36526
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.842
_diffrn_reflns_theta_max         26.430
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4403
_reflns_number_gt                3838
_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 D8 Venture'
_computing_cell_refinement       'Bruker D8 Venture'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0789P)²+5.7360P] 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         4403
_refine_ls_number_parameters     309
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0564
_refine_ls_wR_factor_ref         0.1586
_refine_ls_wR_factor_gt          0.1490
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.064
_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
C1 C 0.02678(19) 0.6589(4) 0.15588(17) 0.0215(6) Uani 1 1 d . . . . .
C2 C 0.0594(2) 0.8193(4) 0.1721(2) 0.0272(7) Uani 1 1 d . . . . .
H2 H 0.0318 0.8964 0.1986 0.033 Uiso 1 1 calc R U . . .
C3 C 0.1343(2) 0.8709(4) 0.14951(19) 0.0267(7) Uani 1 1 d . . . . .
H3 H 0.1571 0.9820 0.1616 0.032 Uiso 1 1 calc R U . . .
C4 C 0.1742(2) 0.7610(4) 0.11017(18) 0.0238(6) Uani 1 1 d . . . . .
C5 C 0.13946(19) 0.5960(4) 0.08985(18) 0.0223(6) Uani 1 1 d . . . . .
C6 C 0.1735(2) 0.4827(4) 0.0450(2) 0.0252(7) Uani 1 1 d . . . . .
H6 H 0.2232 0.5150 0.0286 0.030 Uiso 1 1 calc R U . . .
C7 C 0.1362(2) 0.3269(4) 0.0246(2) 0.0285(7) Uani 1 1 d . . . . .
H7 H 0.1591 0.2536 -0.0070 0.034 Uiso 1 1 calc R U . . .
C8 C 0.0641(2) 0.2745(4) 0.05003(19) 0.0261(7) Uani 1 1 d . . . . .
H8 H 0.0393 0.1651 0.0367 0.031 Uiso 1 1 calc R U . . .
C9 C 0.02943(19) 0.3825(4) 0.09438(17) 0.0220(6) Uani 1 1 d . . . . .
C10 C 0.06495(19) 0.5444(4) 0.11399(17) 0.0207(6) Uani 1 1 d . . . . .
C11 C -0.0506(2) 0.6059(4) 0.18205(17) 0.0227(6) Uani 1 1 d . . . . .
C12 C -0.04678(19) 0.3265(4) 0.12003(17) 0.0225(6) Uani 1 1 d . . . . .
C13 C -0.16194(18) 0.3885(4) 0.18291(17) 0.0224(6) Uani 1 1 d . . . . .
H13A H -0.1998 0.3158 0.1417 0.027 Uiso 1 1 calc R U . . .
H13B H -0.1969 0.4881 0.1899 0.027 Uiso 1 1 calc R U . . .
C14 C -0.0668(2) 0.2840(4) 0.39675(18) 0.0222(6) Uani 1 1 d . . . . .
H14 H -0.0452 0.3437 0.4445 0.027 Uiso 1 1 calc R U . . .
C15 C -0.1015(2) 0.3753(4) 0.32902(18) 0.0230(6) Uani 1 1 d . . . . .
H15 H -0.1044 0.4955 0.3307 0.028 Uiso 1 1 calc R U . . .
C16 C -0.13223(18) 0.2901(4) 0.25852(17) 0.0200(6) Uani 1 1 d . . . . .
C17 C -0.1318(2) 0.1145(4) 0.26008(18) 0.0231(6) Uani 1 1 d . . . . .
H17 H -0.1550 0.0520 0.2134 0.028 Uiso 1 1 calc R U . . .
C18 C -0.0972(2) 0.0307(4) 0.33026(18) 0.0225(6) Uani 1 1 d . . . . .
H18 H -0.0980 -0.0896 0.3308 0.027 Uiso 1 1 calc R U . . .
C19 C 0.3178(2) 0.9669(4) 0.00131(18) 0.0216(6) Uani 1 1 d . . . . .
H19 H 0.3105 1.0371 -0.0432 0.026 Uiso 1 1 calc R U . . .
C20 C 0.2442(2) 0.9194(4) 0.02275(19) 0.0239(6) Uani 1 1 d . . . . .
H20 H 0.1876 0.9577 -0.0065 0.029 Uiso 1 1 calc R U . . .
C21 C 0.2531(2) 0.8161(4) 0.08689(18) 0.0232(6) Uani 1 1 d . . . . .
C22 C 0.3373(2) 0.7625(5) 0.12698(19) 0.0297(7) Uani 1 1 d . . . . .
H22 H 0.3462 0.6907 0.1711 0.036 Uiso 1 1 calc R U . . .
C23 C 0.4082(2) 0.8148(4) 0.10206(19) 0.0267(7) Uani 1 1 d . . . . .
H23 H 0.4653 0.7760 0.1296 0.032 Uiso 1 1 calc R U . . .
Cu1 Cu 0.0000 0.0000 0.5000 0.01783(17) Uani 1 2 d S . P . .
N1 N -0.08447(16) 0.4452(3) 0.15899(14) 0.0206(5) Uani 1 1 d . . . . .
N2 N -0.06256(15) 0.1142(3) 0.39752(14) 0.0189(5) Uani 1 1 d . . . . .
N3 N 0.39962(15) 0.9177(3) 0.04082(14) 0.0188(5) Uani 1 1 d . . . . .
N4 N 0.13911(18) 0.3459(3) 0.53404(17) 0.0268(6) Uani 1 1 d D . . . .
O1 O -0.08247(16) 0.6958(3) 0.22180(15) 0.0329(6) Uani 1 1 d . . . . .
O2 O -0.07694(16) 0.1834(3) 0.10789(14) 0.0310(5) Uani 1 1 d . . . . .
O3 O 0.07873(14) 0.2668(3) 0.55222(13) 0.0244(5) Uani 1 1 d . . . . .
O4 O 0.1229(2) 0.4415(5) 0.4776(2) 0.0444(8) Uiso 0.83 1 d . . P A 1
O5 O 0.2161(2) 0.3320(5) 0.57849(19) 0.0371(7) Uiso 0.83 1 d . . P A 1
O4' O 0.2057(12) 0.413(3) 0.5675(11) 0.055(5) Uiso 0.17 1 d D . P A 2
O5' O 0.1227(10) 0.350(2) 0.4575(8) 0.033(3) Uiso 0.17 1 d D . P A 2
O6 O 0.2717(5) 0.3872(10) 0.2341(5) 0.073(2) Uiso 0.5 1 d . . P B -1
O7 O 0.3954(3) 0.3847(6) 0.1911(3) 0.0595(12) Uiso 0.73 1 d . . P C 1
O8 O 0.3978(5) 0.1945(10) 0.2056(4) 0.0598(17) Uiso 0.49 1 d . . P D 1
O9 O 0.3484(9) 0.2454(17) 0.1993(7) 0.060(3) Uiso 0.28 1 d . . P E 1


_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 C2 1.366(5) . ?
C1 C10 1.415(4) . ?
C1 C11 1.492(4) . ?
C2 C3 1.419(4) . ?
C3 C4 1.379(5) . ?
C4 C5 1.420(4) . ?
C4 C21 1.491(4) . ?
C5 C6 1.408(4) . ?
C5 C10 1.428(4) . ?
C6 C7 1.368(5) . ?
C7 C8 1.408(5) . ?
C8 C9 1.381(5) . ?
C9 C10 1.400(4) . ?
C9 C12 1.477(4) . ?
C11 O1 1.212(4) . ?
C11 N1 1.392(4) . ?
C12 O2 1.222(4) . ?
C12 N1 1.399(4) . ?
C13 N1 1.480(3) . ?
C13 C16 1.514(4) . ?
C14 N2 1.341(4) . ?
C14 C15 1.382(4) . ?
C15 C16 1.389(4) . ?
C16 C17 1.385(5) . ?
C17 C18 1.387(4) . ?
C18 N2 1.344(4) . ?
C19 N3 1.345(4) . ?
C19 C20 1.380(4) . ?
C20 C21 1.382(4) . ?
C21 C22 1.389(5) . ?
C22 C23 1.384(4) . ?
C23 N3 1.340(4) . ?
Cu1 N2 2.030(2) 3_556 ?
Cu1 N2 2.030(2) . ?
Cu1 N3 2.037(2) 4_566 ?
Cu1 N3 2.037(2) 2_545 ?
N3 Cu1 2.037(2) 2_565 ?
N4 O4' 1.181(16) . ?
N4 O4 1.228(4) . ?
N4 O5 1.258(4) . ?
N4 O3 1.260(3) . ?
N4 O5' 1.319(13) . ?

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
C2 C1 C10 120.7(3) . . ?
C2 C1 C11 119.2(3) . . ?
C10 C1 C11 120.1(3) . . ?
C1 C2 C3 120.1(3) . . ?
C4 C3 C2 120.6(3) . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 C21 120.2(3) . . ?
C5 C4 C21 119.4(3) . . ?
C6 C5 C4 123.0(3) . . ?
C6 C5 C10 118.4(3) . . ?
C4 C5 C10 118.6(3) . . ?
C7 C6 C5 121.0(3) . . ?
C6 C7 C8 120.5(3) . . ?
C9 C8 C7 119.8(3) . . ?
C8 C9 C10 120.6(3) . . ?
C8 C9 C12 119.3(3) . . ?
C10 C9 C12 120.1(3) . . ?
C9 C10 C1 120.9(3) . . ?
C9 C10 C5 119.5(3) . . ?
C1 C10 C5 119.6(3) . . ?
O1 C11 N1 121.1(3) . . ?
O1 C11 C1 122.5(3) . . ?
N1 C11 C1 116.4(3) . . ?
O2 C12 N1 120.4(3) . . ?
O2 C12 C9 122.3(3) . . ?
N1 C12 C9 117.2(3) . . ?
N1 C13 C16 109.9(2) . . ?
N2 C14 C15 122.4(3) . . ?
C14 C15 C16 119.5(3) . . ?
C17 C16 C15 117.8(3) . . ?
C17 C16 C13 122.0(3) . . ?
C15 C16 C13 120.2(3) . . ?
C16 C17 C18 119.6(3) . . ?
N2 C18 C17 122.2(3) . . ?
N3 C19 C20 122.8(3) . . ?
C19 C20 C21 119.8(3) . . ?
C20 C21 C22 117.6(3) . . ?
C20 C21 C4 120.6(3) . . ?
C22 C21 C4 121.8(3) . . ?
C23 C22 C21 119.5(3) . . ?
N3 C23 C22 122.8(3) . . ?
N2 Cu1 N2 180.00(13) 3_556 . ?
N2 Cu1 N3 92.77(9) 3_556 4_566 ?
N2 Cu1 N3 87.23(9) . 4_566 ?
N2 Cu1 N3 87.23(9) 3_556 2_545 ?
N2 Cu1 N3 92.77(9) . 2_545 ?
N3 Cu1 N3 180.00(11) 4_566 2_545 ?
C11 N1 C12 125.0(2) . . ?
C11 N1 C13 118.1(3) . . ?
C12 N1 C13 116.7(3) . . ?
C14 N2 C18 118.3(3) . . ?
C14 N2 Cu1 117.6(2) . . ?
C18 N2 Cu1 124.1(2) . . ?
C23 N3 C19 117.5(3) . . ?
C23 N3 Cu1 125.4(2) . 2_565 ?
C19 N3 Cu1 117.0(2) . 2_565 ?
O4 N4 O5 120.8(3) . . ?
O4' N4 O3 136.6(11) . . ?
O4 N4 O3 121.3(3) . . ?
O5 N4 O3 117.7(3) . . ?
O4' N4 O5' 113.4(12) . . ?
O3 N4 O5' 109.9(7) . . ?

_refine_diff_density_max         1.066
_refine_diff_density_min         -1.095
_refine_diff_density_rms         0.098

