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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_z_sq
_database_code_depnum_ccdc_archive 'CCDC 1943325'
loop_
_audit_author_name
_audit_author_address
'Kai Shao'
;Zhejiang University
China
;
_audit_update_record             
;
2019-07-26 deposited with the CCDC.	2019-08-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H18 Cu2 N0 O10'
_chemical_formula_weight         737.58

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      trigonal
_space_group_IT_number           166
_space_group_name_H-M_alt        'R -3 m :H'
_space_group_name_Hall           '-R 3 2"'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z'
'x-y, -y, -z'
'-x, -x+y, -z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+1/3'
'x-y+2/3, -y+1/3, -z+1/3'
'-x+2/3, -x+y+1/3, -z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+2/3'
'x-y+1/3, -y+2/3, -z+2/3'
'-x+1/3, -x+y+2/3, -z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z'
'-x+y, y, z'
'x, x-y, z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z+1/3'
'-x+y+2/3, y+1/3, z+1/3'
'x+2/3, x-y+1/3, z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+2/3'
'-x+y+1/3, y+2/3, z+2/3'
'x+1/3, x-y+2/3, z+2/3'

_cell_length_a                   18.6721(4)
_cell_length_b                   18.6721(4)
_cell_length_c                   52.020(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     15706.8(10)
_cell_formula_units_Z            9
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    45987
_cell_measurement_theta_min      2.368
_cell_measurement_theta_max      25.863

_exptl_crystal_description       Bloc
_exptl_crystal_colour            Blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.702
_exptl_crystal_F_000             3348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_absorpt_coefficient_mu    0.637
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18970
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -63
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_theta_min         1.319
_diffrn_reflns_theta_max         25.863
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3701
_reflns_number_gt                2863
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.1324P)²+24.8917P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.00013(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3701
_refine_ls_number_parameters     162
_refine_ls_number_restraints     115
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.2080
_refine_ls_wR_factor_gt          0.1881
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.85669(2) 0.14331(2) 0.14571(2) 0.0556(3) Uani 1 2 d S T P . .
O1 O 0.92268(19) 0.2249(2) 0.19937(5) 0.0814(8) Uani 1 1 d . . . . .
O2 O 0.96161(16) 0.18450(17) 0.16411(4) 0.0718(7) Uani 1 1 d . . . . .
O3 O 0.89290(19) 0.10710(19) 0.11108(10) 0.143(2) Uani 1 2 d S T P . .
C1 C 0.9723(2) 0.2125(2) 0.18673(6) 0.0643(9) Uani 1 1 d . . . . .
C2 C 1.11009(17) 0.2202(3) 0.18697(8) 0.0617(12) Uani 1 2 d S T P . .
H2A H 1.101525 0.203047 0.169905 0.074 Uiso 1 2 calc R U P . .
C3 C 1.0519(3) 0.2326(3) 0.19940(6) 0.0696(10) Uani 1 1 d . . . . .
C4 C 1.0656(3) 0.2581(3) 0.22506(7) 0.0954(15) Uani 1 1 d . . . . .
H4A H 1.026322 0.265887 0.233677 0.114 Uiso 1 1 calc R U . . .
C5 C 1.1360(3) 0.2720(6) 0.23789(12) 0.118(3) Uani 1 2 d DS T P . .
C6 C 1.1488(17) 0.2981(11) 0.26551(16) 0.207(4) Uani 0.5 1 d D U P A -1
C7 C 1.1665(9) 0.2527(10) 0.28252(14) 0.208(4) Uani 0.5 1 d D U P A -1
H7A H 1.171173 0.208137 0.276663 0.249 Uiso 0.5 1 calc R U P A -1
C8 C 1.1773(10) 0.2734(10) 0.30861(16) 0.216(4) Uani 0.5 1 d D U P A -1
H8A H 1.192709 0.244772 0.319862 0.259 Uiso 0.5 1 calc R U P A -1
C9 C 1.165(2) 0.3357(13) 0.31778(16) 0.223(4) Uani 0.5 1 d D U P A -1
C10 C 1.1681(12) 0.3939(9) 0.30013(18) 0.243(5) Uani 0.5 1 d D U P A -1
C11 C 1.1613(11) 0.3755(9) 0.27396(18) 0.238(5) Uani 0.5 1 d D U P A -1
C12 C 1.1570(15) 0.4310(10) 0.2568(2) 0.274(6) Uani 0.5 1 d D U P A -1
H12A H 1.131376 0.412609 0.240875 0.329 Uiso 0.5 1 calc R U P A -1
C13 C 1.1915(16) 0.5146(10) 0.2636(3) 0.297(6) Uani 0.5 1 d D U P A -1
H13A H 1.215393 0.556641 0.251461 0.357 Uiso 0.5 1 calc R U P A -1
C14 C 1.1883(17) 0.5310(10) 0.2893(3) 0.295(6) Uani 0.5 1 d D U P A -1
H14A H 1.191018 0.579982 0.294413 0.354 Uiso 0.5 1 calc R U P A -1
C15 C 1.1808(15) 0.4722(10) 0.3075(3) 0.277(6) Uani 0.5 1 d D U P A -1
H15A H 1.184191 0.485080 0.324909 0.332 Uiso 0.5 1 calc R U P A -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
Cu1 O2 1.959(2) . ?
Cu1 O2 1.959(2) 22_665 ?
Cu1 O1 1.964(3) 25_655 ?
Cu1 O1 1.964(3) 10_545 ?
Cu1 O3 2.149(4) . ?
Cu1 Cu1 2.6525(9) 25_655 ?
O1 C1 1.248(4) . ?
O2 C1 1.263(4) . ?
C1 C3 1.492(5) . ?
C2 C3 1.380(4) . ?
C2 C3 1.381(4) 23_755 ?
C3 C4 1.397(5) . ?
C4 C5 1.379(5) . ?
C5 C6 1.498(8) . ?
C6 C7 1.376(8) . ?
C6 C11 1.413(8) . ?
C7 C8 1.398(8) . ?
C8 C9 1.373(9) . ?
C9 C10 1.405(8) . ?
C10 C11 1.394(8) . ?
C10 C15 1.412(8) . ?
C11 C12 1.402(8) . ?
C12 C13 1.403(9) . ?
C13 C14 1.378(9) . ?
C14 C15 1.404(9) . ?

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
O2 Cu1 O2 88.26(16) . 22_665 ?
O2 Cu1 O1 167.87(10) . 25_655 ?
O2 Cu1 O1 90.04(13) 22_665 25_655 ?
O2 Cu1 O1 90.04(13) . 10_545 ?
O2 Cu1 O1 167.87(10) 22_665 10_545 ?
O1 Cu1 O1 89.12(19) 25_655 10_545 ?
O2 Cu1 O3 97.06(15) . . ?
O2 Cu1 O3 97.06(15) 22_665 . ?
O1 Cu1 O3 95.07(15) 25_655 . ?
O1 Cu1 O3 95.07(15) 10_545 . ?
O2 Cu1 Cu1 84.15(7) . 25_655 ?
O2 Cu1 Cu1 84.15(7) 22_665 25_655 ?
O1 Cu1 Cu1 83.73(7) 25_655 25_655 ?
O1 Cu1 Cu1 83.73(7) 10_545 25_655 ?
O3 Cu1 Cu1 178.30(19) . 25_655 ?
C1 O1 Cu1 123.1(2) . 25_655 ?
C1 O2 Cu1 122.5(2) . . ?
O1 C1 O2 126.1(3) . . ?
O1 C1 C3 117.3(3) . . ?
O2 C1 C3 116.6(3) . . ?
C3 C2 C3 121.2(4) . 23_755 ?
C2 C3 C4 118.7(3) . . ?
C2 C3 C1 121.3(3) . . ?
C4 C3 C1 119.8(3) . . ?
C5 C4 C3 121.4(4) . . ?
C4 C5 C4 118.6(5) 23_755 . ?
C4 C5 C6 120.9(9) 23_755 . ?
C4 C5 C6 120.5(9) . . ?
C7 C6 C11 117.6(8) . . ?
C7 C6 C5 117.7(7) . . ?
C11 C6 C5 123.3(8) . . ?
C6 C7 C8 120.0(8) . . ?
C9 C8 C7 120.6(8) . . ?
C8 C9 C10 118.1(10) . . ?
C11 C10 C9 118.9(8) . . ?
C11 C10 C15 118.0(8) . . ?
C9 C10 C15 123.1(8) . . ?
C10 C11 C12 118.2(8) . . ?
C10 C11 C6 120.3(8) . . ?
C12 C11 C6 121.1(8) . . ?
C11 C12 C13 119.7(11) . . ?
C14 C13 C12 116.5(12) . . ?
C13 C14 C15 118.6(11) . . ?
C14 C15 C10 121.6(10) . . ?

_refine_diff_density_max         0.847
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.072



