# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_ZJNU-54
_database_code_depnum_ccdc_archive 'CCDC 1480522'
_audit_update_record             
;
2016-05-17 deposited with the CCDC.
2016-07-25 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            'C20 H13 Cu2 N3 O10'
_chemical_formula_weight         582.43

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'
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      hexagonal
_space_group_IT_number           194
_space_group_name_H-M_alt        'P 63/m m c'
_space_group_name_Hall           '-P 6c 2c'

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

_cell_length_a                   18.5653(6)
_cell_length_b                   18.5653(6)
_cell_length_c                   23.9636(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     7153.0(6)
_cell_formula_units_Z            6
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3099
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.6

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.811
_exptl_crystal_F_000             1752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.921
_shelx_estimated_absorpt_T_min   0.809
_shelx_estimated_absorpt_T_max   0.922
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8092
_exptl_absorpt_correction_T_max  0.9217
_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                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            115179
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_av_R_equivalents  0.0866
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.266
_diffrn_reflns_theta_max         27.595
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3099
_reflns_number_gt                2596
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0710P)²+9.8183P] 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         3099
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1025
_refine_ls_R_factor_gt           0.0777
_refine_ls_wR_factor_ref         0.1773
_refine_ls_wR_factor_gt          0.1628
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_restrained_S_all      1.168
_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
Cu1 Cu 0.52377(2) 0.47623(2) -0.04531(2) 0.0380(2) Uani 1 2 d S T P . .
O1 O 0.48134(17) 0.37099(16) -0.00549(11) 0.0508(7) Uani 1 1 d . . . . .
O1W O 0.55958(19) 0.44042(19) -0.1196(2) 0.1029(19) Uani 1 2 d S T P . .
H1WA H 0.5793 0.4820 -0.1422 0.123 Uiso 1 1 d R U . . .
O2 O 0.44018(18) 0.41081(17) 0.07120(11) 0.0502(7) Uani 1 1 d . . . . .
N1 N 0.2389(6) 0.0848(5) 0.2007(3) 0.096(4) Uani 0.5 1 d . . P . .
N2 N 0.4359(8) 0.2577(8) 0.2500 0.091(4) Uani 0.5 2 d S T P . .
H2 H 0.4603 0.2818 0.2181 0.109 Uiso 0.5 1 d R U P . .
C1 C 0.4500(2) 0.3595(2) 0.04287(15) 0.0449(9) Uani 1 1 d . . . . .
C2 C 0.4225(2) 0.2764(2) 0.06923(14) 0.0418(8) Uani 1 1 d . . . . .
C3 C 0.4429(4) 0.22147(18) 0.0435(2) 0.0461(12) Uani 1 2 d S T P . .
H3A H 0.4701 0.2351 0.0092 0.055 Uiso 1 2 calc R U P . .
C4 C 0.3814(3) 0.2556(2) 0.11950(14) 0.0476(9) Uani 1 1 d . . . . .
H4A H 0.3676 0.2921 0.1365 0.057 Uiso 1 1 calc R U . . .
C5 C 0.3603(3) 0.18017(17) 0.1452(2) 0.0467(13) Uani 1 2 d S T P . .
C6 C 0.3167(4) 0.1584(2) 0.2005(2) 0.0556(14) Uani 1 2 d S T P . .
C7 C 0.3576(6) 0.1788(3) 0.2500 0.067(3) Uani 1 4 d S T P . .
C8 C 0.2073(11) 0.0574(11) 0.2500 0.109(7) Uani 0.5 2 d S T P . .
H8A H 0.1540 0.0111 0.2500 0.131 Uiso 0.5 2 d R U P . .


_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 O1 1.952(2) 22_665 ?
Cu1 O1 1.952(2) . ?
Cu1 O2 1.956(3) 10 ?
Cu1 O2 1.956(3) 13_665 ?
Cu1 O1W 2.121(4) . ?
Cu1 Cu1 2.6556(11) 13_665 ?
O1 C1 1.266(4) . ?
O1W H1WA 0.8591 . ?
O2 C1 1.255(4) . ?
O2 Cu1 1.956(3) 13_665 ?
N1 N1 1.286(19) 24 ?
N1 C8 1.304(10) . ?
N1 C6 1.407(10) . ?
N2 C7 1.460(14) . ?
N2 N2 1.48(3) 9 ?
N2 H2 0.8873 . ?
C1 C2 1.501(5) . ?
C2 C4 1.374(5) . ?
C2 C3 1.397(4) . ?
C3 C2 1.397(4) 24 ?
C3 H3A 0.9300 . ?
C4 C5 1.395(5) . ?
C4 H4A 0.9300 . ?
C5 C4 1.395(5) 24 ?
C5 C6 1.500(8) . ?
C6 C7 1.355(7) . ?
C6 N1 1.407(10) 24 ?
C7 C6 1.355(7) 16_556 ?
C7 N2 1.460(14) 9 ?
C8 N1 1.304(10) 16_556 ?
C8 C8 1.72(4) 9 ?
C8 H8A 0.9298 . ?

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
O1 Cu1 O1 89.23(16) 22_665 . ?
O1 Cu1 O2 168.15(11) 22_665 10 ?
O1 Cu1 O2 89.17(12) . 10 ?
O1 Cu1 O2 89.17(12) 22_665 13_665 ?
O1 Cu1 O2 168.15(11) . 13_665 ?
O2 Cu1 O2 89.99(17) 10 13_665 ?
O1 Cu1 O1W 97.45(14) 22_665 . ?
O1 Cu1 O1W 97.45(14) . . ?
O2 Cu1 O1W 94.40(15) 10 . ?
O2 Cu1 O1W 94.40(15) 13_665 . ?
O1 Cu1 Cu1 84.15(8) 22_665 13_665 ?
O1 Cu1 Cu1 84.15(8) . 13_665 ?
O2 Cu1 Cu1 84.00(8) 10 13_665 ?
O2 Cu1 Cu1 84.00(8) 13_665 13_665 ?
O1W Cu1 Cu1 177.74(18) . 13_665 ?
C1 O1 Cu1 122.5(2) . . ?
Cu1 O1W H1WA 107.8 . . ?
C1 O2 Cu1 122.7(2) . 13_665 ?
N1 N1 C8 99.5(10) 24 . ?
N1 N1 C6 62.8(4) 24 . ?
C8 N1 C6 115.2(9) . . ?
C7 N2 N2 59.6(6) . 9 ?
C7 N2 H2 120.4 . . ?
N2 N2 H2 104.4 9 . ?
O2 C1 O1 126.6(3) . . ?
O2 C1 C2 116.7(3) . . ?
O1 C1 C2 116.7(3) . . ?
C4 C2 C3 119.8(4) . . ?
C4 C2 C1 120.9(3) . . ?
C3 C2 C1 119.2(3) . . ?
C2 C3 C2 120.0(5) . 24 ?
C2 C3 H3A 120.0 . . ?
C2 C3 H3A 120.0 24 . ?
C2 C4 C5 120.5(4) . . ?
C2 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C4 C5 C4 119.5(5) . 24 ?
C4 C5 C6 120.3(2) . . ?
C4 C5 C6 120.3(2) 24 . ?
C7 C6 N1 115.4(6) . 24 ?
C7 C6 N1 115.4(6) . . ?
N1 C6 N1 54.4(9) 24 . ?
C7 C6 C5 123.2(6) . . ?
N1 C6 C5 114.7(5) 24 . ?
N1 C6 C5 114.7(5) . . ?
C6 C7 C6 122.0(9) . 16_556 ?
C6 C7 N2 114.7(4) . . ?
C6 C7 N2 114.7(4) 16_556 . ?
C6 C7 N2 114.7(4) . 9 ?
C6 C7 N2 114.7(4) 16_556 9 ?
N2 C7 N2 60.7(12) . 9 ?
N1 C8 N1 129.8(15) . 16_556 ?
N1 C8 C8 80.5(10) . 9 ?
N1 C8 C8 80.5(10) 16_556 9 ?
N1 C8 H8A 115.1 . . ?
N1 C8 H8A 115.1 16_556 . ?
C8 C8 H8A 113.1 9 . ?

# SQUEEZE RESULTS (APPEND TO CIF)
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 -0.046 -0.032 -0.001 4423.7 1229.4
_platon_squeeze_details          
; ?
;

_refine_diff_density_max         0.633
_refine_diff_density_min         -0.717
_refine_diff_density_rms         0.071


_exptl_crystal_recrystallization_method 'solvothermal reaction'
