# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1492970'
_audit_update_record             
;
2016-07-25 deposited with the CCDC.
2016-09-20 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         'C39 H25 Cu3 N6 O13'
_chemical_formula_sum            'C39 H25 Cu3 N6 O13'
_chemical_formula_weight         976.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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        'I 2/m'
_space_group_name_Hall           '-I 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+1/2'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   13.657(5)
_cell_length_b                   18.686(5)
_cell_length_c                   31.503(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 101.532(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     7877(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7804
_cell_measurement_theta_min      6.4580
_cell_measurement_theta_max      71.8460

_exptl_crystal_description       Polyhedral
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.823
_exptl_crystal_F_000             1968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    1.266
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.85582
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
'Empirical absorption correction (CrysAlis RED, Oxford Diffraction)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4223
_diffrn_reflns_number            27001
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         3.327
_diffrn_reflns_theta_max         66.991
_diffrn_reflns_theta_full        66.991
_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             7255
_reflns_number_gt                5213
_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)+(0.1545P)²] 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         7255
_refine_ls_number_parameters     292
_refine_ls_number_restraints     162
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0765
_refine_ls_wR_factor_ref         0.2505
_refine_ls_wR_factor_gt          0.2362
_refine_ls_goodness_of_fit_ref   1.189
_refine_ls_restrained_S_all      1.315
_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 0.90308(5) 0.0000 0.48305(2) 0.0541(3) Uani 1 2 d S T P . .
Cu2 Cu 0.80976(4) 0.28179(3) 0.22732(2) 0.0611(2) Uani 1 1 d . . . . .
O1 O 0.94660(19) 0.07294(17) 0.44649(8) 0.0721(8) Uani 1 1 d . . . . .
O2 O 0.8888(2) 0.07172(17) 0.52632(9) 0.0700(7) Uani 1 1 d . . . . .
O3 O 0.9126(2) 0.24880(18) 0.27533(10) 0.0807(9) Uani 1 1 d . . . . .
O4 O 0.8129(2) 0.19547(17) 0.31376(10) 0.0772(8) Uani 1 1 d . . . . .
O5 O 0.7903(2) 0.36838(14) 0.25983(10) 0.0759(8) Uani 1 1 d . . . . .
O6 O 0.8066(3) 0.18622(15) 0.20053(12) 0.0884(10) Uani 1 1 d . U . . .
O7 O 0.7554(4) 0.0000 0.4435(2) 0.1130(18) Uani 1 2 d S T P . .
N1 N 1.5806(3) 0.1827(2) 0.30805(13) 0.0830(10) Uani 1 1 d D U . . .
N2 N 1.2615(4) 0.1914(4) 0.3564(2) 0.169(2) Uani 1 1 d D U . . .
N3 N 0.6426(10) 0.5000 0.4118(4) 0.192(4) Uani 1 2 d S TU P . .
N4 N 0.6845(6) 0.0000 0.3704(2) 0.115(2) Uani 1 2 d S TU P . .
C1 C 1.5852(5) 0.2054(3) 0.34850(17) 0.1170(16) Uani 1 1 d D U . . .
H1 H 1.6457 0.2261 0.3616 0.140 Uiso 1 1 calc R U . . .
C2 C 1.5132(5) 0.2030(4) 0.3742(2) 0.158(3) Uani 1 1 d D U . . .
H2 H 1.5243 0.2183 0.4028 0.189 Uiso 1 1 calc R U . . .
C3 C 1.4222(5) 0.1749(5) 0.3520(3) 0.178(2) Uani 1 1 d D U . . .
C4 C 1.4151(5) 0.1478(5) 0.3099(3) 0.166(2) Uani 1 1 d D U . . .
H4 H 1.3551 0.1278 0.2957 0.200 Uiso 1 1 calc R U . . .
C5 C 1.4966(4) 0.1500(4) 0.2885(2) 0.136(2) Uani 1 1 d D U . . .
H5 H 1.4918 0.1292 0.2614 0.163 Uiso 1 1 calc R U . . .
C6 C 1.3450(5) 0.1719(6) 0.3787(3) 0.189(2) Uani 1 1 d D U . . .
C7 C 1.1639(4) 0.1823(4) 0.36616(19) 0.109(2) Uani 1 1 d . . . . .
C8 C 1.1480(3) 0.1485(3) 0.40326(16) 0.0905(16) Uani 1 1 d . . . . .
H8 H 1.2022 0.1352 0.4247 0.109 Uiso 1 1 calc R U . . .
C9 C 1.0516(3) 0.1345(2) 0.40859(14) 0.0697(11) Uani 1 1 d . . . . .
C10 C 0.9719(3) 0.1567(2) 0.37820(13) 0.0641(10) Uani 1 1 d . . . . .
H10 H 0.9075 0.1476 0.3823 0.077 Uiso 1 1 calc R U . . .
C11 C 0.9853(3) 0.1925(2) 0.34136(15) 0.0733(12) Uani 1 1 d . . . . .
C12 C 1.0804(4) 0.2061(3) 0.33518(19) 0.1015(19) Uani 1 1 d . . . . .
H12 H 1.0898 0.2308 0.3107 0.122 Uiso 1 1 calc R U . . .
C13 C 1.0350(3) 0.0899(2) 0.44624(13) 0.0659(10) Uani 1 1 d . . . . .
C14 C 0.8967(3) 0.2147(2) 0.30833(14) 0.0673(11) Uani 1 1 d . . . . .
C15 C 0.6656(9) 0.5000 0.3661(3) 0.129(2) Uani 1 2 d S TU P . .
C16 C 0.6853(5) 0.4361(3) 0.34800(19) 0.1112(17) Uani 1 1 d . U . . .
H16 H 0.6720 0.3932 0.3607 0.133 Uiso 1 1 calc R U . . .
C17 C 0.7250(4) 0.4353(2) 0.31075(16) 0.0786(12) Uani 1 1 d . . . . .
C18 C 0.7447(4) 0.5000 0.2920(2) 0.0697(15) Uani 1 2 d S T P . .
H18 H 0.7709 0.5000 0.2669 0.084 Uiso 1 2 calc R U P . .
C19 C 0.7382(3) 0.3677(2) 0.28863(15) 0.0712(11) Uani 1 1 d . . . . .
C20 C 0.7583(8) 0.0000 0.4002(3) 0.126(3) Uani 1 2 d S TU P . .
C21 C 0.5828(7) 0.0000 0.3826(4) 0.149(4) Uani 1 2 d S TU P . .
H21A H 0.5317 0.0000 0.3568 0.224 Uiso 1 2 calc R U P . .
H21B H 0.5761 -0.0419 0.3994 0.224 Uiso 0.5 1 calc R U P . .
H21C H 0.5761 0.0419 0.3994 0.224 Uiso 0.5 1 calc R U P . .
C22 C 0.7032(8) 0.0000 0.3264(3) 0.130(3) Uani 1 2 d S TU P . .
H22A H 0.6407 0.0000 0.3060 0.195 Uiso 1 2 calc R U P . .
H22B H 0.7406 0.0419 0.3221 0.195 Uiso 0.5 1 calc R U P . .
H22C H 0.7406 -0.0419 0.3221 0.195 Uiso 0.5 1 calc R U P . .
H6 H 1.3723(8) 0.177(3) 0.4075(2) 0.156 Uiso 1 1 d D 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
Cu1 O1 1.952(3) 6 ?
Cu1 O1 1.952(3) . ?
Cu1 O2 1.949(3) . ?
Cu1 O2 1.949(3) 6 ?
Cu1 O7 2.148(5) . ?
Cu1 Cu1 2.6492(16) 5_756 ?
Cu2 O3 1.947(3) . ?
Cu2 O4 1.948(3) 7_655 ?
Cu2 O5 1.961(3) . ?
Cu2 O6 1.972(3) . ?
Cu2 N1 2.142(3) 7_755 ?
Cu2 Cu2 2.6554(11) 7_655 ?
O1 C13 1.250(5) . ?
O2 C13 1.259(5) 2_756 ?
O3 C14 1.275(5) . ?
O4 C14 1.244(5) . ?
O4 Cu2 1.948(3) 7_655 ?
O5 C19 1.260(5) . ?
O6 C19 1.260(5) 7_655 ?
O7 C20 1.372(10) . ?
N1 C1 1.333(4) . ?
N1 C5 1.337(4) . ?
N1 Cu2 2.142(3) 7_755 ?
N2 C6 1.267(9) . ?
N2 C7 1.436(7) . ?
N3 C15 1.534(13) . ?
N4 C20 1.233(10) . ?
N4 C22 1.459(12) . ?
N4 C21 1.513(13) . ?
C1 C2 1.393(4) . ?
C2 C3 1.399(5) . ?
C3 C4 1.406(5) . ?
C3 C6 1.475(5) . ?
C4 C5 1.410(5) . ?
C7 C8 1.383(7) . ?
C7 C12 1.416(7) . ?
C8 C9 1.385(6) . ?
C9 C10 1.362(6) . ?
C9 C13 1.503(5) . ?
C10 C11 1.383(5) . ?
C11 C12 1.375(7) . ?
C11 C14 1.488(6) . ?
C13 O2 1.259(5) 2_756 ?
C15 C16 1.373(7) 6_565 ?
C15 C16 1.373(7) . ?
C16 C17 1.388(7) . ?
C17 C18 1.395(5) . ?
C17 C19 1.472(6) . ?
C18 C17 1.395(5) 6_565 ?
C19 O6 1.260(5) 7_655 ?

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 88.56(19) 6 . ?
O1 Cu1 O2 167.83(11) 6 . ?
O1 Cu1 O2 90.99(14) . . ?
O1 Cu1 O2 90.99(14) 6 6 ?
O1 Cu1 O2 167.83(11) . 6 ?
O2 Cu1 O2 86.89(19) . 6 ?
O1 Cu1 O7 91.09(15) 6 . ?
O1 Cu1 O7 91.09(15) . . ?
O2 Cu1 O7 101.08(16) . . ?
O2 Cu1 O7 101.08(16) 6 . ?
O1 Cu1 Cu1 80.81(8) 6 5_756 ?
O1 Cu1 Cu1 80.81(8) . 5_756 ?
O2 Cu1 Cu1 87.11(8) . 5_756 ?
O2 Cu1 Cu1 87.11(8) 6 5_756 ?
O7 Cu1 Cu1 168.63(19) . 5_756 ?
O3 Cu2 O4 167.44(11) . 7_655 ?
O3 Cu2 O5 90.44(14) . . ?
O4 Cu2 O5 88.77(15) 7_655 . ?
O3 Cu2 O6 89.80(16) . . ?
O4 Cu2 O6 88.32(16) 7_655 . ?
O5 Cu2 O6 167.65(12) . . ?
O3 Cu2 N1 91.80(13) . 7_755 ?
O4 Cu2 N1 100.64(13) 7_655 7_755 ?
O5 Cu2 N1 101.43(14) . 7_755 ?
O6 Cu2 N1 90.90(14) . 7_755 ?
O3 Cu2 Cu2 82.29(8) . 7_655 ?
O4 Cu2 Cu2 85.16(9) 7_655 7_655 ?
O5 Cu2 Cu2 85.75(8) . 7_655 ?
O6 Cu2 Cu2 82.05(9) . 7_655 ?
N1 Cu2 Cu2 170.78(11) 7_755 7_655 ?
C13 O1 Cu1 126.1(3) . . ?
C13 O2 Cu1 118.8(2) 2_756 . ?
C14 O3 Cu2 125.3(3) . . ?
C14 O4 Cu2 122.6(3) . 7_655 ?
C19 O5 Cu2 121.5(3) . . ?
C19 O6 Cu2 125.3(3) 7_655 . ?
C20 O7 Cu1 111.5(6) . . ?
C1 N1 C5 117.2(5) . . ?
C1 N1 Cu2 119.6(3) . 7_755 ?
C5 N1 Cu2 121.8(3) . 7_755 ?
C6 N2 C7 128.2(6) . . ?
C20 N4 C22 116.9(9) . . ?
C20 N4 C21 117.3(9) . . ?
C22 N4 C21 125.8(8) . . ?
N1 C1 C2 129.9(6) . . ?
C1 C2 C3 112.5(6) . . ?
C4 C3 C2 119.5(6) . . ?
C4 C3 C6 127.0(7) . . ?
C2 C3 C6 113.2(6) . . ?
C3 C4 C5 121.8(7) . . ?
N1 C5 C4 118.7(6) . . ?
N2 C6 C3 109.9(7) . . ?
C8 C7 N2 122.9(5) . . ?
C8 C7 C12 119.0(4) . . ?
N2 C7 C12 118.0(5) . . ?
C7 C8 C9 120.1(4) . . ?
C10 C9 C8 120.2(4) . . ?
C10 C9 C13 119.8(4) . . ?
C8 C9 C13 119.8(4) . . ?
C9 C10 C11 121.0(4) . . ?
C12 C11 C10 119.7(4) . . ?
C12 C11 C14 120.5(4) . . ?
C10 C11 C14 119.7(4) . . ?
C11 C12 C7 119.9(4) . . ?
O1 C13 O2 126.4(4) . 2_756 ?
O1 C13 C9 116.4(4) . . ?
O2 C13 C9 117.2(3) 2_756 . ?
O4 C14 O3 124.6(4) . . ?
O4 C14 C11 117.7(3) . . ?
O3 C14 C11 117.5(4) . . ?
C16 C15 C16 120.8(8) 6_565 . ?
C16 C15 N3 119.0(4) 6_565 . ?
C16 C15 N3 119.0(4) . . ?
C15 C16 C17 120.2(6) . . ?
C16 C17 C18 119.4(4) . . ?
C16 C17 C19 121.0(4) . . ?
C18 C17 C19 119.4(4) . . ?
C17 C18 C17 120.0(6) 6_565 . ?
O5 C19 O6 125.3(4) . 7_655 ?
O5 C19 C17 118.2(4) . . ?
O6 C19 C17 116.5(4) 7_655 . ?
N4 C20 O7 125.1(10) . . ?

_refine_diff_density_max         1.278
_refine_diff_density_min         -0.770
_refine_diff_density_rms         0.082



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
_platon_squeeze_void_content
1 -0.015 -0.015 -0.013 4736 1044 ' '
_platon_squeeze_details          
;
;


