# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_p-1
_database_code_depnum_ccdc_archive 'CCDC 1509051'
_audit_update_record             
;
2016-10-09 deposited with the CCDC.
2017-05-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H11 Cu2 N O9'
_chemical_formula_sum            'C26 H11 Cu2 N O9'
_chemical_formula_weight         608.46

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           Cubic
_symmetry_space_group_name_H-M   'I m -3 m'
_symmetry_space_group_name_Hall  '-I 4 2 3'

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

_cell_length_a                   31.0977(16)
_cell_length_b                   31.0977(16)
_cell_length_c                   31.0977(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     30074(5)
_cell_formula_units_Z            24
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6095
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      19.56

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.806
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             7296
_exptl_absorpt_coefficient_mu    0.876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9
_exptl_absorpt_correction_T_max  0.916
_exptl_absorpt_process_details   'SADABA, (Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            110179
_diffrn_reflns_av_R_equivalents  0.1554
_diffrn_reflns_av_sigmaI/netI    0.0605
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         0.93
_diffrn_reflns_theta_max         28.29
_reflns_number_total             3543
_reflns_number_gt                2192
_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., SQUEEZE
;

_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)+(0.0703P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3543
_refine_ls_number_parameters     107
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1020
_refine_ls_R_factor_gt           0.0539
_refine_ls_wR_factor_ref         0.1491
_refine_ls_wR_factor_gt          0.1382
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.165
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.126 -0.020 -0.009 19311 4673 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?


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
C1 C 0.46325(16) 0.19506(12) 0.19506(12) 0.0502(14) Uani 1 2 d S . .
H1 H 0.4375 0.2058 0.2058 0.060 Uiso 1 2 calc SR . .
C2 C 0.46145(16) 0.16365(11) 0.16365(11) 0.0474(13) Uani 1 2 d S . .
C3 C 0.5000 0.14681(17) 0.14681(17) 0.052(2) Uani 1 4 d S . .
C4 C 0.5000 0.11264(19) 0.11264(19) 0.094(4) Uani 1 4 d S . .
H4A H 0.5184 0.0894 0.1213 0.141 Uiso 0.25 1 calc PR . .
H4B H 0.5103 0.1246 0.0861 0.141 Uiso 0.25 1 calc PR . .
H4C H 0.4713 0.1021 0.1087 0.141 Uiso 0.25 1 calc PR . .
C5 C 0.41966(18) 0.14990(12) 0.14990(12) 0.0533(14) Uani 1 2 d S . .
C6 C 0.38414(19) 0.14125(14) 0.14125(14) 0.0584(16) Uani 1 2 d S . .
C7 C 0.33946(17) 0.13168(13) 0.13168(13) 0.0513(14) Uani 1 2 d S . .
C8 C 0.31792(12) 0.15470(12) 0.09993(12) 0.0526(10) Uani 1 1 d . . .
H8 H 0.3322 0.1764 0.0851 0.063 Uiso 1 1 calc R . .
C9 C 0.27493(11) 0.14549(12) 0.09011(12) 0.0448(9) Uani 1 1 d . . .
C10 C 0.25425(16) 0.11260(12) 0.11260(12) 0.0449(13) Uani 1 2 d S . .
H10 H 0.2261 0.1055 0.1055 0.054 Uiso 1 2 calc SR . .
C11 C 0.25099(12) 0.17014(12) 0.05702(11) 0.0420(9) Uani 1 1 d . . .
Cu1 Cu 0.180588(17) 0.180588(17) 0.0000 0.0317(2) Uani 1 4 d SU . .
Cu2 Cu 0.240619(18) 0.240619(18) 0.0000 0.0343(2) Uani 1 4 d S . .
N1 N 0.5000 0.21081(12) 0.21081(12) 0.0412(15) Uani 1 4 d S . .
O1 O 0.21657(8) 0.15423(8) 0.04423(8) 0.0513(7) Uani 1 1 d U . .
O2 O 0.26765(8) 0.20455(8) 0.04420(8) 0.0522(7) Uani 1 1 d . . .
O1W O 0.13111(13) 0.13111(13) 0.0000 0.1046(19) Uani 1 4 d SU . .


_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 N1 1.336(6) . ?
C1 C2 1.382(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.409(6) . ?
C2 C5 1.433(7) . ?
C3 C2 1.409(6) 53_655 ?
C3 C4 1.503(11) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.169(7) . ?
C6 C7 1.452(7) . ?
C7 C8 1.391(4) . ?
C7 C8 1.391(4) 64 ?
C8 C9 1.401(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.396(4) . ?
C9 C11 1.484(5) . ?
C10 C9 1.396(4) 64 ?
C10 H10 0.9300 . ?
C11 O1 1.244(4) . ?
C11 O2 1.254(4) . ?
Cu1 O1 1.953(2) 56 ?
Cu1 O1 1.953(2) 6 ?
Cu1 O1 1.953(2) . ?
Cu1 O1 1.953(2) 51 ?
Cu1 O1W 2.176(6) . ?
Cu1 Cu2 2.6401(11) . ?
Cu2 O2 1.963(2) 6 ?
Cu2 O2 1.963(2) 56 ?
Cu2 O2 1.963(2) . ?
Cu2 O2 1.963(2) 51 ?
Cu2 N1 2.136(5) 89 ?
N1 C1 1.336(6) 53_655 ?
N1 Cu2 2.136(5) 81 ?

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
N1 C1 C2 123.5(5) . . ?
N1 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?
C1 C2 C3 119.4(5) . . ?
C1 C2 C5 117.3(5) . . ?
C3 C2 C5 123.3(5) . . ?
C2 C3 C2 116.6(7) 53_655 . ?
C2 C3 C4 121.7(3) 53_655 . ?
C2 C3 C4 121.7(3) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C2 174.1(7) . . ?
C5 C6 C7 177.8(7) . . ?
C8 C7 C8 119.9(5) . 64 ?
C8 C7 C6 120.0(2) . . ?
C8 C7 C6 120.0(2) 64 . ?
C7 C8 C9 120.6(4) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C10 C9 C8 118.7(4) . . ?
C10 C9 C11 119.7(3) . . ?
C8 C9 C11 121.6(3) . . ?
C9 C10 C9 121.5(5) . 64 ?
C9 C10 H10 119.3 . . ?
C9 C10 H10 119.3 64 . ?
O1 C11 O2 126.4(3) . . ?
O1 C11 C9 116.6(3) . . ?
O2 C11 C9 117.0(3) . . ?
O1 Cu1 O1 89.51(16) 56 6 ?
O1 Cu1 O1 89.15(16) 56 . ?
O1 Cu1 O1 167.56(15) 6 . ?
O1 Cu1 O1 167.56(15) 56 51 ?
O1 Cu1 O1 89.15(16) 6 51 ?
O1 Cu1 O1 89.51(16) . 51 ?
O1 Cu1 O1W 96.22(7) 56 . ?
O1 Cu1 O1W 96.22(7) 6 . ?
O1 Cu1 O1W 96.22(7) . . ?
O1 Cu1 O1W 96.22(7) 51 . ?
O1 Cu1 Cu2 83.78(7) 56 . ?
O1 Cu1 Cu2 83.78(7) 6 . ?
O1 Cu1 Cu2 83.78(7) . . ?
O1 Cu1 Cu2 83.78(7) 51 . ?
O1W Cu1 Cu2 180.00(15) . . ?
O2 Cu2 O2 88.88(16) 6 56 ?
O2 Cu2 O2 168.38(15) 6 . ?
O2 Cu2 O2 89.95(16) 56 . ?
O2 Cu2 O2 89.95(16) 6 51 ?
O2 Cu2 O2 168.38(15) 56 51 ?
O2 Cu2 O2 88.88(16) . 51 ?
O2 Cu2 N1 95.81(7) 6 89 ?
O2 Cu2 N1 95.81(7) 56 89 ?
O2 Cu2 N1 95.81(7) . 89 ?
O2 Cu2 N1 95.81(7) 51 89 ?
O2 Cu2 Cu1 84.19(7) 6 . ?
O2 Cu2 Cu1 84.19(7) 56 . ?
O2 Cu2 Cu1 84.19(7) . . ?
O2 Cu2 Cu1 84.19(7) 51 . ?
N1 Cu2 Cu1 180.00(15) 89 . ?
C1 N1 C1 117.6(6) . 53_655 ?
C1 N1 Cu2 121.2(3) . 81 ?
C1 N1 Cu2 121.2(3) 53_655 81 ?
C11 O1 Cu1 123.4(2) . . ?
C11 O2 Cu2 122.2(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.0 . . . . ?
N1 C1 C2 C5 180.0 . . . . ?
C1 C2 C3 C2 0.0 . . . 53_655 ?
C5 C2 C3 C2 180.0 . . . 53_655 ?
C1 C2 C3 C4 180.0 . . . . ?
C5 C2 C3 C4 0.0 . . . . ?
C1 C2 C5 C6 0.000(2) . . . . ?
C3 C2 C5 C6 180.0(4) . . . . ?
C2 C5 C6 C7 0.000(10) . . . . ?
C5 C6 C7 C8 89.5(5) . . . . ?
C5 C6 C7 C8 -89.5(5) . . . 64 ?
C8 C7 C8 C9 -1.6(9) 64 . . . ?
C6 C7 C8 C9 179.4(5) . . . . ?
C7 C8 C9 C10 -0.4(7) . . . . ?
C7 C8 C9 C11 178.7(4) . . . . ?
C8 C9 C10 C9 2.5(8) . . . 64 ?
C11 C9 C10 C9 -176.7(3) . . . 64 ?
C10 C9 C11 O1 -15.4(6) . . . . ?
C8 C9 C11 O1 165.4(4) . . . . ?
C10 C9 C11 O2 165.7(4) . . . . ?
C8 C9 C11 O2 -13.5(6) . . . . ?
O1 Cu1 Cu2 O2 -89.82(11) 56 . . 6 ?
O1 Cu1 Cu2 O2 0.36(11) 6 . . 6 ?
O1 Cu1 Cu2 O2 -179.64(11) . . . 6 ?
O1 Cu1 Cu2 O2 90.18(11) 51 . . 6 ?
O1W Cu1 Cu2 O2 135.27(8) . . . 6 ?
O1 Cu1 Cu2 O2 -0.36(11) 56 . . 56 ?
O1 Cu1 Cu2 O2 89.82(11) 6 . . 56 ?
O1 Cu1 Cu2 O2 -90.18(11) . . . 56 ?
O1 Cu1 Cu2 O2 179.64(11) 51 . . 56 ?
O1W Cu1 Cu2 O2 -135.27(8) . . . 56 ?
O1 Cu1 Cu2 O2 90.18(11) 56 . . . ?
O1 Cu1 Cu2 O2 -179.64(11) 6 . . . ?
O1 Cu1 Cu2 O2 0.36(11) . . . . ?
O1 Cu1 Cu2 O2 -89.82(11) 51 . . . ?
O1W Cu1 Cu2 O2 -44.73(8) . . . . ?
O1 Cu1 Cu2 O2 179.64(11) 56 . . 51 ?
O1 Cu1 Cu2 O2 -90.18(11) 6 . . 51 ?
O1 Cu1 Cu2 O2 89.82(11) . . . 51 ?
O1 Cu1 Cu2 O2 -0.36(11) 51 . . 51 ?
O1W Cu1 Cu2 O2 44.73(8) . . . 51 ?
O1 Cu1 Cu2 N1 134.91(8) 56 . . 89 ?
O1 Cu1 Cu2 N1 -134.91(8) 6 . . 89 ?
O1 Cu1 Cu2 N1 45.09(8) . . . 89 ?
O1 Cu1 Cu2 N1 -45.09(8) 51 . . 89 ?
O1W Cu1 Cu2 N1 0(36) . . . 89 ?
C2 C1 N1 C1 0.0 . . . 53_655 ?
C2 C1 N1 Cu2 180.0 . . . 81 ?
O2 C11 O1 Cu1 0.2(6) . . . . ?
C9 C11 O1 Cu1 -178.6(2) . . . . ?
O1 Cu1 O1 C11 -84.2(3) 56 . . . ?
O1 Cu1 O1 C11 -0.4(3) 6 . . . ?
O1 Cu1 O1 C11 83.4(3) 51 . . . ?
O1W Cu1 O1 C11 179.6(3) . . . . ?
Cu2 Cu1 O1 C11 -0.4(3) . . . . ?
O1 C11 O2 Cu2 0.3(6) . . . . ?
C9 C11 O2 Cu2 179.1(2) . . . . ?
O2 Cu2 O2 C11 -0.5(3) 6 . . . ?
O2 Cu2 O2 C11 83.7(3) 56 . . . ?
O2 Cu2 O2 C11 -84.7(3) 51 . . . ?
N1 Cu2 O2 C11 179.5(3) 89 . . . ?
Cu1 Cu2 O2 C11 -0.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        28.29
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.030
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.087
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
