# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1491604'
_audit_update_record             
;
2016-07-08 deposited with the CCDC.
2016-08-26 downloaded from the CCDC.
;

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
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 0.000 0.000 -0.052 1425 281 ' '
_platon_squeeze_details          
;
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H25 Cu N3 O8'
_chemical_formula_weight         559.02

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'

_symmetry_cell_setting           trigonal
_symmetry_space_group_name_H-M   P3121

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

_cell_length_a                   22.4258(16)
_cell_length_b                   22.4258(16)
_cell_length_c                   10.9190(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     4755.6(8)
_cell_formula_units_Z            6
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7478
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      25.30

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1734
_exptl_absorpt_coefficient_mu    0.732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8857
_exptl_absorpt_correction_T_max  0.9304
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25299
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         25.99
_reflns_number_total             6211
_reflns_number_gt                5382
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1668P)²+3.0415P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.12(3)
_refine_ls_number_reflns         6211
_refine_ls_number_parameters     336
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.0875
_refine_ls_R_factor_gt           0.0803
_refine_ls_wR_factor_ref         0.2286
_refine_ls_wR_factor_gt          0.2218
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.052
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.33696(4) 0.0000 0.3333 0.0347(2) Uani 1 2 d S . .
Cu2 Cu 0.33679(4) 0.33679(4) 0.0000 0.0368(2) Uani 1 2 d S . .
C1 C 0.4427(3) 0.3260(3) 0.0799(6) 0.0442(13) Uani 1 1 d . . .
C2 C 0.4808(3) 0.2899(3) 0.1231(6) 0.0471(13) Uani 1 1 d . . .
C3 C 0.4441(3) 0.2225(3) 0.1638(5) 0.0402(10) Uani 1 1 d . . .
H3 H 0.3962 0.1993 0.1669 0.048 Uiso 1 1 calc R . .
C4 C 0.4816(3) 0.1894(3) 0.2011(5) 0.0469(13) Uani 1 1 d . . .
C5 C 0.5505(4) 0.2221(4) 0.1851(9) 0.071(2) Uani 1 1 d . . .
H5 H 0.5741 0.1995 0.2079 0.085 Uiso 1 1 calc R . .
C6 C 0.5859(5) 0.2849(6) 0.1384(11) 0.089(3) Uani 1 1 d . . .
C7 C 0.5515(4) 0.3230(4) 0.1125(9) 0.067(2) Uani 1 1 d . . .
H7 H 0.5763 0.3690 0.0891 0.081 Uiso 1 1 calc R . .
C8 C 0.4408(3) 0.1169(3) 0.2461(6) 0.0456(13) Uani 1 1 d . . .
C9 C 0.6629(4) 0.3215(5) 0.1110(6) 0.068(2) Uani 1 1 d . . .
C10 C 0.7069(4) 0.3915(5) 0.1125(8) 0.074(2) Uani 1 1 d . . .
H10 H 0.6883 0.4199 0.1246 0.089 Uiso 1 1 calc R . .
C11 C 0.7715(5) 0.4194(5) 0.0983(10) 0.086(3) Uani 1 1 d . . .
H11 H 0.7988 0.4672 0.0986 0.103 Uiso 1 1 calc R . .
C12 C 0.8019(5) 0.3780(5) 0.0819(9) 0.081(2) Uani 1 1 d . . .
H12 H 0.8493 0.3970 0.0746 0.097 Uiso 1 1 calc R . .
C13 C 0.7576(4) 0.3078(5) 0.0774(8) 0.070(2) Uani 1 1 d . . .
C14 C 0.7825(4) 0.2585(5) 0.0500(8) 0.072(2) Uani 1 1 d . . .
C15 C 0.7538(5) 0.1944(5) 0.1054(11) 0.092(3) Uani 1 1 d . . .
H15 H 0.7187 0.1820 0.1624 0.111 Uiso 1 1 calc R . .
C16 C 0.7766(4) 0.1477(4) 0.0774(7) 0.0615(19) Uani 1 1 d . . .
C17 C 0.8340(4) 0.1679(4) 0.0006(6) 0.0553(14) Uani 1 1 d . . .
H17 H 0.8537 0.1402 -0.0076 0.066 Uiso 1 1 calc R . .
C18 C 0.8603(4) 0.2286(4) -0.0618(7) 0.0646(19) Uani 1 1 d U . .
C19 C 0.8363(5) 0.2769(5) -0.0306(9) 0.078(2) Uani 1 1 d U . .
H19 H 0.8577 0.3205 -0.0658 0.094 Uiso 1 1 calc R . .
C20 C 0.7482(4) 0.0813(4) 0.1494(7) 0.0567(17) Uani 1 1 d . . .
C21 C 0.9194(4) 0.2515(4) -0.1481(7) 0.0547(16) Uani 1 1 d . . .
O8 O 0.9493(2) 0.3152(3) -0.1802(4) 0.0577(11) Uani 1 1 d . . .
N1 N 0.6893(3) 0.2789(4) 0.0978(6) 0.0660(17) Uani 1 1 d . . .
O1 O 0.3759(2) 0.2896(3) 0.0870(4) 0.0533(11) Uani 1 1 d . . .
O2 O 0.4723(3) 0.3845(3) 0.0427(6) 0.0803(18) Uani 1 1 d . . .
O3 O 0.3760(2) 0.0887(2) 0.2465(5) 0.0534(10) Uani 1 1 d . . .
O4 O 0.4714(3) 0.0860(3) 0.2819(6) 0.0759(17) Uani 1 1 d . . .
O5 O 0.6870(3) 0.0535(2) 0.1832(4) 0.0622(12) Uani 1 1 d . . .
O6 O 0.7867(4) 0.0585(4) 0.1802(7) 0.098(2) Uani 1 1 d . . .
O7 O 0.9352(4) 0.2084(4) -0.1818(7) 0.097(2) Uani 1 1 d . . .
N2 N 0.5398(8) 0.0342(8) 0.1487(14) 0.155(5) Uani 1 1 d DU . .
H2A H 0.5339 0.0609 0.2031 0.186 Uiso 1 1 calc R . .
H2B H 0.5684 0.0214 0.1820 0.186 Uiso 1 1 calc R . .
C22 C 0.4697(9) -0.0303(8) 0.1203(17) 0.168(6) Uani 1 1 d DU . .
H22A H 0.4546 -0.0602 0.1902 0.253 Uiso 1 1 calc R . .
H22B H 0.4745 -0.0541 0.0514 0.253 Uiso 1 1 calc R . .
H22C H 0.4364 -0.0166 0.1016 0.253 Uiso 1 1 calc R . .
C23 C 0.5710(11) 0.0742(13) 0.033(2) 0.235(10) Uani 1 1 d DU . .
H23A H 0.6150 0.1135 0.0517 0.352 Uiso 1 1 calc R . .
H23B H 0.5412 0.0892 -0.0003 0.352 Uiso 1 1 calc R . .
H23C H 0.5768 0.0454 -0.0248 0.352 Uiso 1 1 calc R . .
C24 C 0.9240(12) 0.1628(9) 0.5520(19) 0.196(9) Uani 1 1 d DU . .
H24A H 0.9674 0.2050 0.5524 0.294 Uiso 1 1 calc R . .
H24B H 0.9279 0.1284 0.5980 0.294 Uiso 1 1 calc R . .
H24C H 0.8895 0.1706 0.5884 0.294 Uiso 1 1 calc R . .
C25 C 0.8383(11) 0.0657(10) 0.427(2) 0.205(9) Uani 1 1 d DU . .
H25A H 0.8229 0.0513 0.3442 0.308 Uiso 1 1 calc R . .
H25B H 0.8026 0.0673 0.4724 0.308 Uiso 1 1 calc R . .
H25C H 0.8490 0.0335 0.4643 0.308 Uiso 1 1 calc R . .
N3 N 0.9044(13) 0.1391(10) 0.425(2) 0.255(9) Uani 1 1 d DU . .
H3A H 0.9390 0.1372 0.3871 0.306 Uiso 1 1 calc R . .
H3B H 0.8957 0.1687 0.3837 0.306 Uiso 1 1 calc R . .


_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 O8 1.942(4) 4_545 ?
Cu1 O8 1.942(4) 3_665 ?
Cu1 O3 1.970(4) . ?
Cu1 O3 1.970(4) 6 ?
Cu2 O1 1.930(4) 4 ?
Cu2 O1 1.930(4) . ?
Cu2 O5 1.942(4) 3_664 ?
Cu2 O5 1.942(4) 5_665 ?
C1 O2 1.208(8) . ?
C1 O1 1.301(8) . ?
C1 C2 1.517(8) . ?
C2 C7 1.378(10) . ?
C2 C3 1.384(8) . ?
C3 C4 1.431(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.350(11) . ?
C4 C8 1.495(9) . ?
C5 C6 1.326(13) . ?
C5 H5 0.9300 . ?
C6 C7 1.438(12) . ?
C6 C9 1.525(12) . ?
C7 H7 0.9300 . ?
C8 O4 1.256(8) . ?
C8 O3 1.262(8) . ?
C9 N1 1.361(12) . ?
C9 C10 1.373(13) . ?
C10 C11 1.268(13) . ?
C10 H10 0.9300 . ?
C11 C12 1.413(14) . ?
C11 H11 0.9300 . ?
C12 C13 1.380(13) . ?
C12 H12 0.9300 . ?
C13 N1 1.350(11) . ?
C13 C14 1.497(13) . ?
C14 C19 1.379(12) . ?
C14 C15 1.385(12) . ?
C15 C16 1.410(12) . ?
C15 H15 0.9300 . ?
C16 C17 1.407(9) . ?
C16 C20 1.515(9) . ?
C17 C18 1.365(10) . ?
C17 H17 0.9300 . ?
C18 C19 1.468(13) . ?
C18 C21 1.494(9) . ?
C19 H19 0.9300 . ?
C20 O5 1.246(9) . ?
C20 O6 1.249(10) . ?
C21 O7 1.239(10) . ?
C21 O8 1.286(9) . ?
O8 Cu1 1.942(4) 2_654 ?
O5 Cu2 1.942(4) 2_655 ?
N2 C23 1.499(19) . ?
N2 C22 1.545(16) . ?
N2 H2A 0.9000 . ?
N2 H2B 0.9000 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 N3 1.47(2) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 N3 1.571(19) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
N3 H3A 0.9000 . ?
N3 H3B 0.9000 . ?

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
O8 Cu1 O8 175.3(3) 4_545 3_665 ?
O8 Cu1 O3 91.8(2) 4_545 . ?
O8 Cu1 O3 88.5(2) 3_665 . ?
O8 Cu1 O3 88.5(2) 4_545 6 ?
O8 Cu1 O3 91.8(2) 3_665 6 ?
O3 Cu1 O3 173.1(3) . 6 ?
O1 Cu2 O1 174.6(3) 4 . ?
O1 Cu2 O5 92.9(2) 4 3_664 ?
O1 Cu2 O5 87.3(2) . 3_664 ?
O1 Cu2 O5 87.3(2) 4 5_665 ?
O1 Cu2 O5 92.9(2) . 5_665 ?
O5 Cu2 O5 176.0(4) 3_664 5_665 ?
O2 C1 O1 122.4(6) . . ?
O2 C1 C2 122.3(6) . . ?
O1 C1 C2 115.2(5) . . ?
C7 C2 C3 120.8(5) . . ?
C7 C2 C1 119.3(5) . . ?
C3 C2 C1 119.7(5) . . ?
C2 C3 C4 118.3(5) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C5 C4 C3 119.5(6) . . ?
C5 C4 C8 122.9(5) . . ?
C3 C4 C8 117.3(5) . . ?
C6 C5 C4 122.7(7) . . ?
C6 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
C5 C6 C7 119.6(8) . . ?
C5 C6 C9 124.3(8) . . ?
C7 C6 C9 116.2(9) . . ?
C2 C7 C6 118.5(7) . . ?
C2 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
O4 C8 O3 122.1(6) . . ?
O4 C8 C4 119.8(6) . . ?
O3 C8 C4 118.1(5) . . ?
N1 C9 C10 119.1(8) . . ?
N1 C9 C6 114.6(8) . . ?
C10 C9 C6 125.9(9) . . ?
C11 C10 C9 123.7(10) . . ?
C11 C10 H10 118.2 . . ?
C9 C10 H10 118.2 . . ?
C10 C11 C12 119.9(10) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C13 C12 C11 116.5(9) . . ?
C13 C12 H12 121.7 . . ?
C11 C12 H12 121.7 . . ?
N1 C13 C12 122.6(8) . . ?
N1 C13 C14 115.6(7) . . ?
C12 C13 C14 121.8(8) . . ?
C19 C14 C15 118.2(8) . . ?
C19 C14 C13 120.0(8) . . ?
C15 C14 C13 121.8(7) . . ?
C14 C15 C16 121.5(8) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C17 C16 C15 120.2(6) . . ?
C17 C16 C20 119.6(6) . . ?
C15 C16 C20 119.2(6) . . ?
C18 C17 C16 119.2(6) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C17 C18 C19 119.0(6) . . ?
C17 C18 C21 121.6(7) . . ?
C19 C18 C21 118.8(6) . . ?
C14 C19 C18 121.0(7) . . ?
C14 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
O5 C20 O6 122.0(6) . . ?
O5 C20 C16 117.5(6) . . ?
O6 C20 C16 120.2(7) . . ?
O7 C21 O8 126.2(6) . . ?
O7 C21 C18 118.1(7) . . ?
O8 C21 C18 115.7(6) . . ?
C21 O8 Cu1 115.4(4) . 2_654 ?
C13 N1 C9 118.0(7) . . ?
C1 O1 Cu2 108.8(4) . . ?
C8 O3 Cu1 109.1(4) . . ?
C20 O5 Cu2 116.9(5) . 2_655 ?
C23 N2 C22 110.1(12) . . ?
C23 N2 H2A 109.6 . . ?
C22 N2 H2A 109.6 . . ?
C23 N2 H2B 109.6 . . ?
C22 N2 H2B 109.6 . . ?
H2A N2 H2B 108.2 . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N2 C23 H23A 109.5 . . ?
N2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N3 C24 H24A 109.5 . . ?
N3 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N3 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N3 C25 H25A 109.5 . . ?
N3 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N3 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 N3 C25 108.9(16) . . ?
C24 N3 H3A 109.9 . . ?
C25 N3 H3A 109.9 . . ?
C24 N3 H3B 109.9 . . ?
C25 N3 H3B 109.9 . . ?
H3A N3 H3B 108.3 . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         1.082
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.117
