# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_New
_database_code_depnum_ccdc_archive 'CCDC 1032156'
_audit_update_record             
;
2014-11-19 deposited with the CCDC.
2014-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H14 Cu2 N4 O9'
_chemical_formula_weight         605.45

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/m

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

_cell_length_a                   17.2044(9)
_cell_length_b                   25.9374(14)
_cell_length_c                   14.6116(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.672(6)
_cell_angle_gamma                90.00
_cell_volume                     6407.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9195
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      58.92

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.628
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1216
_exptl_absorpt_coefficient_mu    1.021
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.775
_exptl_absorpt_correction_T_max  0.876
_exptl_absorpt_process_details   CrysAlisPro

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3592
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9195
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_sigmaI/netI    0.0684
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         58.92
_reflns_number_total             4705
_reflns_number_gt                3258
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Oxford Diffraction Ltd., 2010)'
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction Ltd., 2010)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction Ltd., 2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond 3.1a (Brandenburg, 2005)'
_computing_publication_material  'PLATON (Spek, 2009)'

_refine_special_details          SQUEEZE

# 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 -0.008 -0.008 -0.065 4631 1049 ' '
_platon_squeeze_details          
;

Because the solvent molecules and chlorine ions are highly disordered, 
it is impossible to reasonably map out these guest molecules based on the diffraction. 
Therefore, the SQUEEZE subroutine of the PLATON software suits was used to remove the 
scattering from the highly disordered guest molecules.
About two chlorine ions, two 2DMF and four water lattice guests were removed from the 
formula unit by the SQUEEZE process.
;

_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)+(0.0801P)²+11.3320P] 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_number_reflns         4705
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1055
_refine_ls_R_factor_gt           0.0881
_refine_ls_wR_factor_ref         0.2199
_refine_ls_wR_factor_gt          0.2086
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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 0.07797(5) 0.0000 0.51289(6) 0.0665(3) Uani 1 2 d S . .
Cu2 Cu -0.2500 0.2500 1.0000 0.0907(4) Uani 1 2 d S . .
O1 O -0.0609(2) 0.05292(13) 0.5846(2) 0.0781(9) Uani 1 1 d . . .
O2 O 0.0706(2) 0.05298(14) 0.6065(3) 0.0868(10) Uani 1 1 d . . .
O3 O 0.2219(3) 0.1614(2) 0.8595(4) 0.142(2) Uani 1 1 d . . .
O4 O 0.1588(2) 0.22310(16) 0.9154(3) 0.0916(11) Uani 1 1 d . . .
O5 O 0.2034(5) 0.0000 0.5228(5) 0.139(2) Uani 1 2 d S . .
H5B H 0.2246 0.0000 0.4706 0.167 Uiso 1 2 d S . .
H5C H 0.2356 0.0000 0.5790 0.167 Uiso 1 2 d S . .
N1 N -0.2101(3) 0.21743(18) 0.8951(3) 0.0827(12) Uani 1 1 d . . .
N2 N -0.1296(3) 0.18402(19) 0.8128(3) 0.0881(13) Uani 1 1 d . . .
C1 C -0.2518(5) 0.2049(4) 0.8078(5) 0.132(3) Uani 1 1 d . . .
H1A H -0.3060 0.2094 0.7886 0.158 Uiso 1 1 calc R . .
C2 C -0.2046(4) 0.1859(3) 0.7560(6) 0.132(3) Uani 1 1 d . . .
H2A H -0.2181 0.1757 0.6940 0.159 Uiso 1 1 calc R . .
C3 C -0.1385(3) 0.2031(2) 0.8934(4) 0.0780(13) Uani 1 1 d . . .
H3A H -0.0973 0.2060 0.9442 0.094 Uiso 1 1 calc R . .
C4 C -0.0584(3) 0.1642(2) 0.7881(4) 0.0795(13) Uani 1 1 d . . .
C5 C -0.0617(3) 0.1274(2) 0.7200(4) 0.0805(14) Uani 1 1 d . . .
H5A H -0.1104 0.1152 0.6891 0.097 Uiso 1 1 calc R . .
C6 C 0.0074(3) 0.1086(2) 0.6975(3) 0.0792(13) Uani 1 1 d . . .
C7 C 0.0800(3) 0.1272(2) 0.7447(4) 0.0815(14) Uani 1 1 d . . .
H7A H 0.1267 0.1140 0.7307 0.098 Uiso 1 1 calc R . .
C8 C 0.0834(3) 0.1653(2) 0.8128(4) 0.0822(14) Uani 1 1 d . . .
C9 C 0.0132(3) 0.1838(2) 0.8323(4) 0.0831(14) Uani 1 1 d . . .
H9A H 0.0141 0.2100 0.8760 0.100 Uiso 1 1 calc R . .
C10 C 0.0058(3) 0.0688(2) 0.6236(3) 0.0737(13) Uani 1 1 d . . .
C11 C 0.1621(4) 0.1834(2) 0.8663(4) 0.0864(15) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0727(6) 0.0656(6) 0.0645(6) 0.000 0.0213(4) 0.000
Cu2 0.1000(8) 0.1022(8) 0.0769(7) 0.0188(6) 0.0345(6) 0.0416(6)
O1 0.075(2) 0.081(2) 0.079(2) -0.0105(18) 0.0170(17) 0.0020(17)
O2 0.091(2) 0.082(2) 0.088(2) -0.0131(19) 0.0189(19) 0.0036(19)
O3 0.095(3) 0.164(5) 0.161(5) -0.053(4) 0.005(3) -0.004(3)
O4 0.102(3) 0.097(3) 0.079(2) -0.014(2) 0.0239(19) -0.026(2)
O5 0.181(7) 0.101(5) 0.131(5) 0.000 0.017(5) 0.000
N1 0.081(3) 0.095(3) 0.072(3) -0.003(2) 0.014(2) 0.013(2)
N2 0.080(3) 0.102(3) 0.083(3) -0.016(3) 0.017(2) 0.006(2)
C1 0.105(5) 0.174(8) 0.119(6) -0.033(5) 0.027(4) 0.032(5)
C2 0.111(5) 0.161(7) 0.121(5) -0.033(5) 0.012(5) 0.018(5)
C3 0.076(3) 0.092(4) 0.067(3) -0.007(3) 0.016(2) 0.010(3)
C4 0.079(3) 0.079(3) 0.082(3) -0.007(3) 0.018(3) 0.003(3)
C5 0.082(3) 0.086(3) 0.074(3) -0.015(3) 0.017(3) 0.002(3)
C6 0.084(3) 0.081(3) 0.074(3) -0.011(3) 0.018(3) 0.000(3)
C7 0.071(3) 0.094(4) 0.082(3) -0.014(3) 0.021(3) -0.002(3)
C8 0.082(3) 0.088(4) 0.079(3) -0.013(3) 0.021(3) -0.006(3)
C9 0.079(3) 0.091(4) 0.082(3) -0.020(3) 0.021(3) -0.003(3)
C10 0.075(3) 0.076(3) 0.071(3) -0.012(3) 0.016(3) -0.003(3)
C11 0.084(4) 0.091(4) 0.084(4) -0.013(3) 0.014(3) -0.014(3)

_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 O2 1.959(4) . ?
Cu1 O2 1.959(4) 6 ?
Cu1 O1 1.960(3) 5_556 ?
Cu1 O1 1.960(3) 2_556 ?
Cu1 O5 2.136(9) . ?
Cu1 Cu1 2.6391(18) 5_556 ?
Cu2 O4 1.939(4) 2_557 ?
Cu2 O4 1.939(4) 8_455 ?
Cu2 N1 1.980(4) . ?
Cu2 N1 1.980(4) 7_457 ?
O1 C10 1.253(6) . ?
O1 Cu1 1.960(3) 5_556 ?
O2 C10 1.257(6) . ?
O3 C11 1.195(7) . ?
O4 C11 1.263(7) . ?
O4 Cu2 1.939(4) 2_557 ?
O5 H5B 0.9034 . ?
O5 H5C 0.9012 . ?
N1 C3 1.292(6) . ?
N1 C1 1.382(8) . ?
N2 C3 1.312(6) . ?
N2 C2 1.401(8) . ?
N2 C4 1.434(6) . ?
C1 C2 1.305(9) . ?
C1 H1A 0.9300 . ?
C2 H2A 0.9300 . ?
C3 H3A 0.9300 . ?
C4 C5 1.371(7) . ?
C4 C9 1.378(7) . ?
C5 C6 1.381(7) . ?
C5 H5A 0.9300 . ?
C6 C7 1.396(7) . ?
C6 C10 1.489(7) . ?
C7 C8 1.396(7) . ?
C7 H7A 0.9300 . ?
C8 C9 1.379(7) . ?
C8 C11 1.507(8) . ?
C9 H9A 0.9300 . ?

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
O2 Cu1 O2 89.1(2) . 6 ?
O2 Cu1 O1 167.92(15) . 5_556 ?
O2 Cu1 O1 89.76(15) 6 5_556 ?
O2 Cu1 O1 89.76(15) . 2_556 ?
O2 Cu1 O1 167.92(15) 6 2_556 ?
O1 Cu1 O1 88.9(2) 5_556 2_556 ?
O2 Cu1 O5 98.49(18) . . ?
O2 Cu1 O5 98.49(18) 6 . ?
O1 Cu1 O5 93.57(18) 5_556 . ?
O1 Cu1 O5 93.57(18) 2_556 . ?
O2 Cu1 Cu1 84.52(11) . 5_556 ?
O2 Cu1 Cu1 84.52(11) 6 5_556 ?
O1 Cu1 Cu1 83.40(10) 5_556 5_556 ?
O1 Cu1 Cu1 83.40(10) 2_556 5_556 ?
O5 Cu1 Cu1 175.7(2) . 5_556 ?
O4 Cu2 O4 180.000(1) 2_557 8_455 ?
O4 Cu2 N1 89.11(16) 2_557 . ?
O4 Cu2 N1 90.89(16) 8_455 . ?
O4 Cu2 N1 90.89(16) 2_557 7_457 ?
O4 Cu2 N1 89.11(16) 8_455 7_457 ?
N1 Cu2 N1 180.00(14) . 7_457 ?
C10 O1 Cu1 124.2(3) . 5_556 ?
C10 O2 Cu1 122.8(3) . . ?
C11 O4 Cu2 122.6(4) . 2_557 ?
Cu1 O5 H5B 120.2 . . ?
Cu1 O5 H5C 120.3 . . ?
H5B O5 H5C 119.5 . . ?
C3 N1 C1 104.3(5) . . ?
C3 N1 Cu2 127.4(4) . . ?
C1 N1 Cu2 128.3(4) . . ?
C3 N2 C2 105.7(5) . . ?
C3 N2 C4 127.5(5) . . ?
C2 N2 C4 126.8(5) . . ?
C2 C1 N1 110.6(7) . . ?
C2 C1 H1A 124.7 . . ?
N1 C1 H1A 124.7 . . ?
C1 C2 N2 105.9(7) . . ?
C1 C2 H2A 127.1 . . ?
N2 C2 H2A 127.1 . . ?
N1 C3 N2 113.4(5) . . ?
N1 C3 H3A 123.3 . . ?
N2 C3 H3A 123.3 . . ?
C5 C4 C9 120.7(5) . . ?
C5 C4 N2 120.6(5) . . ?
C9 C4 N2 118.6(5) . . ?
C4 C5 C6 119.8(5) . . ?
C4 C5 H5A 120.1 . . ?
C6 C5 H5A 120.1 . . ?
C5 C6 C7 119.4(5) . . ?
C5 C6 C10 121.0(5) . . ?
C7 C6 C10 119.5(5) . . ?
C8 C7 C6 120.8(5) . . ?
C8 C7 H7A 119.6 . . ?
C6 C7 H7A 119.6 . . ?
C9 C8 C7 118.1(5) . . ?
C9 C8 C11 121.5(5) . . ?
C7 C8 C11 120.3(5) . . ?
C4 C9 C8 121.1(5) . . ?
C4 C9 H9A 119.5 . . ?
C8 C9 H9A 119.5 . . ?
O1 C10 O2 125.0(5) . . ?
O1 C10 C6 116.8(5) . . ?
O2 C10 C6 118.1(5) . . ?
O3 C11 O4 124.5(6) . . ?
O3 C11 C8 120.8(6) . . ?
O4 C11 C8 114.7(6) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        58.92
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         1.365
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.084
