# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1049485'
_audit_update_record             
;
2015-02-14 deposited with the CCDC.
2015-05-05 downloaded from the CCDC.
;
_audit_creation_date             2015-02-05
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.06 svn.r2239, GUI svn.r4109)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H10 Cu4 N6 O12'
_chemical_formula_sum            'C12 H10 Cu4 N6 O12'
_chemical_formula_weight         684.42
_chemical_melting_point          ?
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   8.105(3)
_cell_length_b                   16.969(5)
_cell_length_c                   17.666(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.495(5)
_cell_angle_gamma                90.00
_cell_volume                     2372.0(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_exptl_absorpt_coefficient_mu    3.604
_exptl_absorpt_correction_T_max  0.7145
_exptl_absorpt_correction_T_min  0.6139
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.917
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0673
_diffrn_reflns_av_unetI/netI     0.0777
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11662
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.40
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3016
_reflns_number_total             4175
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         2.067
_refine_diff_density_min         -1.488
_refine_diff_density_rms         0.158
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0560
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0793P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1423
_refine_ls_wR_factor_ref         0.1511
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.00577(10) 0.70429(5) 0.28783(5) 0.0254(3) Uani 1 1 d . . .
Cu2 Cu 0.20535(10) 0.60267(5) 0.17002(5) 0.0192(2) Uani 1 1 d . . .
Cu3 Cu 0.53558(10) 0.66737(5) -0.02707(5) 0.0239(2) Uani 1 1 d . . .
Cu4 Cu 0.40762(11) 0.58083(5) -0.20244(6) 0.0324(3) Uani 1 1 d . . .
C1 C -0.1085(9) 0.6557(5) 0.0586(4) 0.0342(19) Uani 1 1 d . . .
H1 H -0.0739 0.6367 0.0139 0.041 Uiso 1 1 calc R . .
C2 C -0.2579(9) 0.7021(4) 0.1338(4) 0.0281(17) Uani 1 1 d . . .
H2 H -0.3500 0.7228 0.1529 0.034 Uiso 1 1 calc R . .
C3 C -0.2799(9) 0.8275(4) 0.2783(4) 0.0270(17) Uani 1 1 d . . .
H3 H -0.2816 0.8455 0.2273 0.032 Uiso 1 1 calc R . .
C4 C -0.2176(8) 0.7659(4) 0.3839(4) 0.0251(16) Uani 1 1 d . . .
H4 H -0.1654 0.7309 0.4239 0.030 Uiso 1 1 calc R . .
C5 C 0.3047(10) 0.6978(4) 0.3974(4) 0.0265(17) Uani 1 1 d . . .
C6 C 0.3482(10) 0.6543(4) 0.3268(4) 0.0311(18) Uani 1 1 d . . .
H6 H 0.4478 0.6814 0.3134 0.037 Uiso 1 1 calc R . .
C7 C 0.3965(12) 0.5704(5) 0.3462(4) 0.043(2) Uani 1 1 d . . .
H7A H 0.2981 0.5423 0.3581 0.051 Uiso 1 1 calc R . .
H7B H 0.4884 0.5691 0.3933 0.051 Uiso 1 1 calc R . .
C8 C 0.4541(9) 0.5276(5) 0.2820(4) 0.0300(18) Uani 1 1 d . . .
C9 C 0.2884(10) 0.5872(5) 0.0237(4) 0.0329(19) Uani 1 1 d . . .
C10 C 0.2711(12) 0.5553(8) -0.0588(5) 0.070(4) Uani 1 1 d . . .
H10 H 0.3089 0.4991 -0.0571 0.084 Uiso 1 1 calc R . .
C11 C 0.1135(15) 0.5622(9) -0.1050(6) 0.090(4) Uani 1 1 d . . .
H11A H 0.0873 0.6191 -0.1115 0.109 Uiso 1 1 calc R . .
H11B H 0.0321 0.5392 -0.0767 0.109 Uiso 1 1 calc R . .
C12 C 0.0796(10) 0.5248(5) -0.1863(4) 0.0359(19) Uani 1 1 d . . .
N1 N -0.3420(7) 0.8139(3) 0.3898(3) 0.0217(13) Uani 1 1 d . . .
N2 N -0.3820(7) 0.8540(3) 0.3206(3) 0.0224(13) Uani 1 1 d . . .
N3 N -0.1722(7) 0.7720(3) 0.3146(3) 0.0236(13) Uani 1 1 d . . .
N4 N -0.1050(7) 0.6876(3) 0.1778(3) 0.0221(13) Uani 1 1 d . . .
N5 N -0.0103(7) 0.6583(4) 0.1291(3) 0.0264(14) Uani 1 1 d . . .
N6 N -0.2652(7) 0.6837(4) 0.0589(3) 0.0311(15) Uani 1 1 d . . .
O1 O 0.1557(6) 0.7234(3) 0.3897(3) 0.0295(12) Uani 1 1 d . . .
O1W O -0.1144(8) 0.5957(3) 0.3379(3) 0.0470(15) Uani 1 1 d . . .
O2 O 0.4187(6) 0.7065(3) 0.4567(3) 0.0289(12) Uani 1 1 d . . .
O2W O 0.2535(13) 0.6820(6) -0.2832(6) 0.123(3) Uiso 1 1 d . . .
O3 O 0.2099(6) 0.6623(3) 0.2626(3) 0.0244(11) Uani 1 1 d . . .
O4 O 0.4176(6) 0.5512(3) 0.2118(3) 0.0271(11) Uani 1 1 d . . .
O5 O 0.5370(6) 0.4637(3) 0.2994(3) 0.0328(13) Uani 1 1 d . . .
O6 O 0.1947(6) 0.5578(3) 0.0656(3) 0.0306(12) Uani 1 1 d . . .
O7 O 0.4012(6) 0.6378(3) 0.0472(3) 0.0306(12) Uani 1 1 d . . .
O8 O 0.3824(7) 0.6059(4) -0.0989(4) 0.0511(18) Uani 1 1 d . . .
O9 O 0.1979(7) 0.5208(4) -0.2227(4) 0.0543(18) Uani 1 1 d . . .
O10 O -0.0627(7) 0.5044(3) -0.2143(3) 0.0397(14) Uani 1 1 d . . .


_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 N3 1.979(5) . ?
Cu1 N4 1.978(6) . ?
Cu1 O1 1.968(5) . ?
Cu1 O1W 2.345(5) . ?
Cu1 O3 1.939(4) . ?
Cu2 N5 1.980(6) . ?
Cu2 O3 1.917(5) . ?
Cu2 O4 1.928(5) . ?
Cu2 O6 1.980(5) . ?
Cu2 O10 2.375(5) 3_565 ?
Cu3 N1 1.968(5) 4_675 ?
Cu3 N6 1.982(6) 1_655 ?
Cu3 O2 2.333(5) 4_575 ?
Cu3 O7 1.944(5) . ?
Cu3 O8 1.886(6) . ?
Cu4 N2 1.999(6) 4_675 ?
Cu4 O2W 2.402(11) . ?
Cu4 O4 2.675(5) 3_665 ?
Cu4 O5 2.010(5) 3_665 ?
Cu4 O8 1.932(6) . ?
Cu4 O9 1.947(5) . ?
C1 H1 0.9500 . ?
C1 N5 1.325(9) . ?
C1 N6 1.357(9) . ?
C2 H2 0.9500 . ?
C2 N4 1.336(9) . ?
C2 N6 1.348(9) . ?
C3 H3 0.9500 . ?
C3 N2 1.309(9) . ?
C3 N3 1.348(9) . ?
C4 H4 0.9500 . ?
C4 N1 1.318(8) . ?
C4 N3 1.357(9) . ?
C5 C6 1.555(10) . ?
C5 O1 1.262(8) . ?
C5 O2 1.246(9) . ?
C6 H6 1.0000 . ?
C6 C7 1.497(10) . ?
C6 O3 1.418(8) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.502(10) . ?
C8 O4 1.276(9) . ?
C8 O5 1.278(9) . ?
C9 C10 1.533(11) . ?
C9 O6 1.273(9) . ?
C9 O7 1.257(9) . ?
C10 H10 1.0000 . ?
C10 C11 1.364(14) . ?
C10 O8 1.526(12) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.540(12) . ?
C12 O9 1.267(9) . ?
C12 O10 1.203(9) . ?
N1 Cu3 1.968(5) 4_476 ?
N1 N2 1.375(7) . ?
N2 Cu4 1.999(6) 4_476 ?
N4 N5 1.365(7) . ?
N6 Cu3 1.982(6) 1_455 ?
O2 Cu3 2.333(5) 4_576 ?
O5 Cu4 2.010(5) 3_665 ?
O10 Cu2 2.375(5) 3_565 ?

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
N3 Cu1 O1W 89.0(2) . . ?
N4 Cu1 N3 96.8(2) . . ?
N4 Cu1 O1W 97.0(2) . . ?
O1 Cu1 N3 91.4(2) . . ?
O1 Cu1 N4 169.0(2) . . ?
O1 Cu1 O1W 90.5(2) . . ?
O3 Cu1 N3 165.9(2) . . ?
O3 Cu1 N4 87.1(2) . . ?
O3 Cu1 O1 83.22(19) . . ?
O3 Cu1 O1W 104.0(2) . . ?
N5 Cu2 O10 91.8(2) . 3_565 ?
O3 Cu2 N5 85.0(2) . . ?
O3 Cu2 O4 93.55(19) . . ?
O3 Cu2 O6 170.7(2) . . ?
O3 Cu2 O10 92.5(2) . 3_565 ?
O4 Cu2 N5 178.3(2) . . ?
O4 Cu2 O6 92.2(2) . . ?
O4 Cu2 O10 89.1(2) . 3_565 ?
O6 Cu2 N5 89.2(2) . . ?
O6 Cu2 O10 94.95(19) . 3_565 ?
N1 Cu3 N6 95.2(2) 4_675 1_655 ?
N1 Cu3 O2 91.0(2) 4_675 4_575 ?
N6 Cu3 O2 102.0(2) 1_655 4_575 ?
O7 Cu3 N1 172.8(2) . 4_675 ?
O7 Cu3 N6 90.1(2) . 1_655 ?
O7 Cu3 O2 92.7(2) . 4_575 ?
O8 Cu3 N1 87.3(2) . 4_675 ?
O8 Cu3 N6 154.3(3) . 1_655 ?
O8 Cu3 O2 103.6(2) . 4_575 ?
O8 Cu3 O7 85.9(2) . . ?
N2 Cu4 O2W 92.1(3) 4_675 . ?
N2 Cu4 O4 92.0(2) 4_675 3_665 ?
N2 Cu4 O5 92.5(2) 4_675 3_665 ?
O2W Cu4 O4 140.9(3) . 3_665 ?
O5 Cu4 O2W 86.9(3) 3_665 . ?
O5 Cu4 O4 54.10(17) 3_665 3_665 ?
O8 Cu4 N2 86.9(2) . 4_675 ?
O8 Cu4 O2W 104.9(3) . . ?
O8 Cu4 O4 114.1(2) . 3_665 ?
O8 Cu4 O5 168.2(3) . 3_665 ?
O8 Cu4 O9 91.3(2) . . ?
O9 Cu4 N2 177.5(2) . 4_675 ?
O9 Cu4 O2W 86.8(3) . . ?
O9 Cu4 O4 90.2(2) . 3_665 ?
O9 Cu4 O5 89.6(2) . 3_665 ?
N5 C1 H1 124.5 . . ?
N5 C1 N6 111.0(6) . . ?
N6 C1 H1 124.5 . . ?
N4 C2 H2 124.3 . . ?
N4 C2 N6 111.5(6) . . ?
N6 C2 H2 124.3 . . ?
N2 C3 H3 123.4 . . ?
N2 C3 N3 113.2(6) . . ?
N3 C3 H3 123.4 . . ?
N1 C4 H4 123.7 . . ?
N1 C4 N3 112.7(6) . . ?
N3 C4 H4 123.7 . . ?
O1 C5 C6 117.0(6) . . ?
O2 C5 C6 118.4(6) . . ?
O2 C5 O1 124.6(6) . . ?
C5 C6 H6 107.8 . . ?
C7 C6 C5 111.2(6) . . ?
C7 C6 H6 107.8 . . ?
O3 C6 C5 108.6(6) . . ?
O3 C6 H6 107.8 . . ?
O3 C6 C7 113.3(6) . . ?
C6 C7 H7A 108.9 . . ?
C6 C7 H7B 108.9 . . ?
C6 C7 C8 113.3(7) . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
O4 C8 C7 122.5(7) . . ?
O5 C8 C7 117.5(7) . . ?
O5 C8 O4 119.9(7) . . ?
O6 C9 C10 118.1(8) . . ?
O7 C9 C10 117.8(7) . . ?
O7 C9 O6 123.9(7) . . ?
C9 C10 H10 110.1 . . ?
C11 C10 C9 114.8(9) . . ?
C11 C10 H10 110.1 . . ?
C11 C10 O8 104.2(10) . . ?
O8 C10 C9 107.4(8) . . ?
O8 C10 H10 110.1 . . ?
C10 C11 H11A 107.7 . . ?
C10 C11 H11B 107.7 . . ?
C10 C11 C12 118.5(10) . . ?
H11A C11 H11B 107.1 . . ?
C12 C11 H11A 107.7 . . ?
C12 C11 H11B 107.7 . . ?
O9 C12 C11 119.6(8) . . ?
O10 C12 C11 117.6(8) . . ?
O10 C12 O9 122.6(7) . . ?
C4 N1 Cu3 132.6(5) . 4_476 ?
C4 N1 N2 105.9(5) . . ?
N2 N1 Cu3 121.6(4) . 4_476 ?
C3 N2 Cu4 133.7(5) . 4_476 ?
C3 N2 N1 106.3(5) . . ?
N1 N2 Cu4 118.8(4) . 4_476 ?
C3 N3 Cu1 136.3(5) . . ?
C3 N3 C4 102.0(6) . . ?
C4 N3 Cu1 121.7(5) . . ?
C2 N4 Cu1 135.4(5) . . ?
C2 N4 N5 106.2(6) . . ?
N5 N4 Cu1 118.3(4) . . ?
C1 N5 Cu2 129.1(5) . . ?
C1 N5 N4 107.4(5) . . ?
N4 N5 Cu2 121.0(4) . . ?
C1 N6 Cu3 123.8(5) . 1_455 ?
C2 N6 Cu3 129.8(5) . 1_455 ?
C2 N6 C1 104.0(6) . . ?
C5 O1 Cu1 115.4(4) . . ?
C5 O2 Cu3 114.8(4) . 4_576 ?
Cu2 O3 Cu1 122.0(2) . . ?
C6 O3 Cu1 114.7(4) . . ?
C6 O3 Cu2 119.8(4) . . ?
C8 O4 Cu2 120.9(4) . . ?
C8 O5 Cu4 108.5(5) . 3_665 ?
C9 O6 Cu2 118.7(5) . . ?
C9 O7 Cu3 115.2(5) . . ?
Cu3 O8 Cu4 124.7(3) . . ?
C10 O8 Cu3 111.6(5) . . ?
C10 O8 Cu4 120.6(5) . . ?
C12 O9 Cu4 127.2(5) . . ?
C12 O10 Cu2 125.2(6) . 3_565 ?

_platon_squeeze_details          ?
# 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 -0.011 0.000 0.000 211 50 ' '
2 0.001 0.500 0.500 211 50 ' '

