# 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_xb7608_0m
_database_code_depnum_ccdc_archive 'CCDC 1015201'
_audit_update_record             
;
2014-07-21 deposited with the CCDC.
2014-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H18 Cu4 N21 Na'
_chemical_formula_weight         733.62

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'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7330(8)
_cell_length_b                   8.9376(8)
_cell_length_c                   16.4561(14)
_cell_angle_alpha                86.8620(10)
_cell_angle_beta                 76.7910(10)
_cell_angle_gamma                80.6080(10)
_cell_volume                     1233.48(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.975
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    3.469
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6152
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_sigmaI/netI    0.0447
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4284
_reflns_number_gt                3580
_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)+(0.0614P)²+0.9455P] 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         4284
_refine_ls_number_parameters     349
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1150
_refine_ls_wR_factor_gt          0.1037
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.001

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
N20 N 0.6408(4) 0.1339(4) -0.0418(2) 0.0196(8) Uani 1 1 d . . .
Cu1 Cu 0.45415(6) -0.00625(7) 0.11582(4) 0.02119(17) Uani 1 1 d . . .
Cu2 Cu 0.74846(7) 0.15682(7) 0.18685(4) 0.02174(17) Uani 1 1 d . . .
Cu4 Cu 0.89868(7) -0.51101(6) 0.23996(4) 0.02323(17) Uani 1 1 d . . .
Cu3 Cu 1.09821(7) -0.17552(7) 0.19238(4) 0.02530(18) Uani 1 1 d . . .
N7 N 0.7427(4) -0.0727(4) 0.1860(3) 0.0211(9) Uani 1 1 d . . .
N12 N 0.6408(5) 0.2828(5) 0.2875(2) 0.0219(9) Uani 1 1 d . . .
N6 N 0.8513(4) -0.1837(4) 0.1991(3) 0.0207(9) Uani 1 1 d . . .
N14 N 0.1075(4) 0.0559(4) 0.1846(3) 0.0205(9) Uani 1 1 d . . .
N15 N -0.0154(4) 0.1664(4) 0.1955(3) 0.0199(9) Uani 1 1 d . . .
N18 N 0.6090(4) 0.1267(4) 0.0398(2) 0.0189(8) Uani 1 1 d . . .
N19 N 0.7153(5) 0.1951(5) 0.0675(2) 0.0209(9) Uani 1 1 d . . .
N21 N 0.7656(5) 0.2060(5) -0.0697(2) 0.0223(9) Uani 1 1 d . . .
N5 N 0.8046(4) -0.3176(4) 0.1903(3) 0.0217(9) Uani 1 1 d . . .
N11 N 0.7076(5) 0.3946(5) 0.3125(2) 0.0225(9) Uani 1 1 d . . .
N8 N 0.6202(4) -0.1314(4) 0.1680(3) 0.0214(9) Uani 1 1 d . . .
N4 N 1.1198(5) -0.3154(4) 0.2908(2) 0.0207(9) Uani 1 1 d . . .
N16 N 0.0404(4) 0.3006(4) 0.1889(3) 0.0220(9) Uani 1 1 d . . .
N13 N 0.2445(4) 0.1154(5) 0.1685(3) 0.0242(9) Uani 1 1 d . . .
N3 N 1.0251(5) -0.4234(5) 0.3139(2) 0.0232(9) Uani 1 1 d . . .
N10 N 0.6266(5) 0.4388(5) 0.3878(3) 0.0278(10) Uani 1 1 d . . .
C4 C 0.6631(5) -0.2818(5) 0.1707(3) 0.0214(10) Uani 1 1 d . . .
N9 N 0.5064(5) 0.3569(5) 0.4129(3) 0.0339(11) Uani 1 1 d . . .
C11 C 0.8082(6) 0.2405(6) -0.0016(3) 0.0250(11) Uani 1 1 d . . .
C6 C 0.1992(5) 0.2650(5) 0.1713(3) 0.0241(11) Uani 1 1 d . . .
N2 N 1.0446(5) -0.4844(6) 0.3854(3) 0.0357(11) Uani 1 1 d . . .
C49 C 0.9436(8) 0.3210(8) -0.0015(4) 0.0533(19) Uani 1 1 d . . .
H49A H 1.0374 0.2483 -0.0010 0.080 Uiso 1 1 calc R . .
H49B H 0.9193 0.3824 0.0472 0.080 Uiso 1 1 calc R . .
H49C H 0.9619 0.3845 -0.0506 0.080 Uiso 1 1 calc R . .
C2 C 1.2004(6) -0.3183(6) 0.3516(3) 0.0288(12) Uani 1 1 d . . .
C8 C 0.5183(6) 0.2647(6) 0.3506(3) 0.0286(12) Uani 1 1 d . . .
N1 N 1.1545(6) -0.4190(6) 0.4107(3) 0.0385(12) Uani 1 1 d . . .
C5 C 0.3091(6) 0.3792(6) 0.1580(4) 0.0448(16) Uani 1 1 d . . .
H5A H 0.2571 0.4735 0.1394 0.067 Uiso 1 1 calc R . .
H5B H 0.4031 0.3437 0.1165 0.067 Uiso 1 1 calc R . .
H5C H 0.3382 0.3940 0.2095 0.067 Uiso 1 1 calc R . .
C1 C 1.3197(8) -0.2188(8) 0.3540(4) 0.0505(17) Uani 1 1 d . . .
H1A H 1.2672 -0.1265 0.3817 0.076 Uiso 1 1 calc R . .
H1B H 1.3730 -0.1957 0.2980 0.076 Uiso 1 1 calc R . .
H1C H 1.3963 -0.2699 0.3838 0.076 Uiso 1 1 calc R . .
C3 C 0.5673(7) -0.3940(6) 0.1527(4) 0.0428(16) Uani 1 1 d . . .
H3A H 0.4573 -0.3634 0.1789 0.064 Uiso 1 1 calc R . .
H3B H 0.6043 -0.4920 0.1741 0.064 Uiso 1 1 calc R . .
H3C H 0.5785 -0.3990 0.0934 0.064 Uiso 1 1 calc R . .
C7 C 0.4134(8) 0.1498(8) 0.3497(4) 0.056(2) Uani 1 1 d . . .
H7A H 0.4381 0.0663 0.3862 0.084 Uiso 1 1 calc R . .
H7B H 0.4302 0.1138 0.2940 0.084 Uiso 1 1 calc R . .
H7C H 0.3041 0.1949 0.3684 0.084 Uiso 1 1 calc R . .
C10 C 0.1549(9) 0.0541(9) 0.5738(4) 0.0563(18) Uani 1 1 d . . .
N17 N 0.2073(10) 0.1611(8) 0.5562(4) 0.082(2) Uani 1 1 d . . .
C9 C 0.0922(10) -0.0852(9) 0.5962(5) 0.072(2) Uani 1 1 d . . .
H9A H 0.1154 -0.1477 0.5479 0.108 Uiso 1 1 calc R . .
H9B H -0.0210 -0.0632 0.6168 0.108 Uiso 1 1 calc R . .
H9C H 0.1403 -0.1377 0.6387 0.108 Uiso 1 1 calc R . .
Na1 Na 0.2546(2) 0.4299(2) 0.52210(12) 0.0325(5) 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
N20 N18 1.307(5) . ?
N20 N21 1.335(5) . ?
N20 Cu1 2.097(4) 2_655 ?
Cu1 N13 2.003(4) . ?
Cu1 N8 2.006(4) . ?
Cu1 N18 2.096(4) . ?
Cu1 N20 2.097(4) 2_655 ?
Cu2 N12 2.011(4) . ?
Cu2 N19 2.052(4) . ?
Cu2 N7 2.061(4) . ?
Cu2 N15 2.115(4) 1_655 ?
Cu4 N5 2.005(4) . ?
Cu4 N16 2.019(4) 1_645 ?
Cu4 N3 2.077(4) . ?
Cu4 N11 2.088(4) 1_545 ?
Cu3 N4 2.016(4) . ?
Cu3 N14 2.079(4) 1_655 ?
Cu3 N21 2.103(4) 2_755 ?
Cu3 N6 2.147(4) . ?
N7 N6 1.301(5) . ?
N7 N8 1.361(5) . ?
N12 C8 1.334(6) . ?
N12 N11 1.361(5) . ?
N6 N5 1.351(5) . ?
N14 N15 1.321(5) . ?
N14 N13 1.354(5) . ?
N14 Cu3 2.079(4) 1_455 ?
N15 N16 1.356(5) . ?
N15 Cu2 2.115(4) 1_455 ?
N18 N19 1.362(5) . ?
N19 C11 1.324(6) . ?
N21 C11 1.325(6) . ?
N21 Cu3 2.103(4) 2_755 ?
N5 C4 1.332(6) . ?
N11 N10 1.324(5) . ?
N11 Cu4 2.088(4) 1_565 ?
N8 C4 1.336(6) . ?
N4 C2 1.345(6) . ?
N4 N3 1.355(5) . ?
N16 C6 1.338(6) . ?
N16 Cu4 2.019(4) 1_465 ?
N13 C6 1.331(6) . ?
N3 N2 1.305(6) . ?
N10 N9 1.352(6) . ?
N10 Na1 2.438(4) 2_666 ?
C4 C3 1.488(7) . ?
N9 C8 1.325(6) . ?
N9 Na1 2.519(5) . ?
C11 C49 1.481(7) . ?
C6 C5 1.486(7) . ?
N2 N1 1.352(6) . ?
N2 Na1 2.688(5) 2_656 ?
C2 N1 1.327(7) . ?
C2 C1 1.485(7) . ?
C8 C7 1.487(7) . ?
N1 Na1 2.454(5) 1_645 ?
C10 N17 1.122(9) . ?
C10 C9 1.437(11) . ?
N17 Na1 2.516(7) . ?
Na1 N10 2.438(4) 2_666 ?
Na1 N1 2.454(5) 1_465 ?
Na1 N2 2.688(5) 2_656 ?

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
N18 N20 N21 109.7(3) . . ?
N18 N20 Cu1 123.9(3) . 2_655 ?
N21 N20 Cu1 124.9(3) . 2_655 ?
N13 Cu1 N8 130.48(17) . . ?
N13 Cu1 N18 112.55(16) . . ?
N8 Cu1 N18 95.80(15) . . ?
N13 Cu1 N20 95.01(16) . 2_655 ?
N8 Cu1 N20 112.87(16) . 2_655 ?
N18 Cu1 N20 110.03(14) . 2_655 ?
N12 Cu2 N19 126.92(16) . . ?
N12 Cu2 N7 121.80(16) . . ?
N19 Cu2 N7 94.38(16) . . ?
N12 Cu2 N15 96.39(15) . 1_655 ?
N19 Cu2 N15 112.74(15) . 1_655 ?
N7 Cu2 N15 103.22(14) . 1_655 ?
N5 Cu4 N16 132.69(16) . 1_645 ?
N5 Cu4 N3 99.61(16) . . ?
N16 Cu4 N3 105.74(16) 1_645 . ?
N5 Cu4 N11 106.42(15) . 1_545 ?
N16 Cu4 N11 100.57(16) 1_645 1_545 ?
N3 Cu4 N11 111.40(16) . 1_545 ?
N4 Cu3 N14 126.83(15) . 1_655 ?
N4 Cu3 N21 125.97(16) . 2_755 ?
N14 Cu3 N21 91.45(16) 1_655 2_755 ?
N4 Cu3 N6 96.70(15) . . ?
N14 Cu3 N6 102.83(14) 1_655 . ?
N21 Cu3 N6 111.53(15) 2_755 . ?
N6 N7 N8 108.9(4) . . ?
N6 N7 Cu2 127.8(3) . . ?
N8 N7 Cu2 123.2(3) . . ?
C8 N12 N11 104.6(4) . . ?
C8 N12 Cu2 131.9(3) . . ?
N11 N12 Cu2 122.3(3) . . ?
N7 N6 N5 109.7(3) . . ?
N7 N6 Cu3 127.5(3) . . ?
N5 N6 Cu3 119.5(3) . . ?
N15 N14 N13 109.6(4) . . ?
N15 N14 Cu3 126.5(3) . 1_455 ?
N13 N14 Cu3 123.9(3) . 1_455 ?
N14 N15 N16 108.3(3) . . ?
N14 N15 Cu2 128.2(3) . 1_455 ?
N16 N15 Cu2 121.0(3) . 1_455 ?
N20 N18 N19 108.9(3) . . ?
N20 N18 Cu1 126.1(3) . . ?
N19 N18 Cu1 123.8(3) . . ?
C11 N19 N18 104.1(4) . . ?
C11 N19 Cu2 131.8(3) . . ?
N18 N19 Cu2 121.0(3) . . ?
C11 N21 N20 104.9(4) . . ?
C11 N21 Cu3 129.7(3) . 2_755 ?
N20 N21 Cu3 120.7(3) . 2_755 ?
C4 N5 N6 105.4(4) . . ?
C4 N5 Cu4 129.2(3) . . ?
N6 N5 Cu4 121.8(3) . . ?
N10 N11 N12 109.1(4) . . ?
N10 N11 Cu4 125.9(3) . 1_565 ?
N12 N11 Cu4 124.9(3) . 1_565 ?
C4 N8 N7 105.2(3) . . ?
C4 N8 Cu1 130.0(3) . . ?
N7 N8 Cu1 122.4(3) . . ?
C2 N4 N3 104.8(4) . . ?
C2 N4 Cu3 133.7(4) . . ?
N3 N4 Cu3 120.9(3) . . ?
C6 N16 N15 105.6(4) . . ?
C6 N16 Cu4 130.2(3) . 1_465 ?
N15 N16 Cu4 120.4(3) . 1_465 ?
C6 N13 N14 105.2(4) . . ?
C6 N13 Cu1 130.1(3) . . ?
N14 N13 Cu1 121.8(3) . . ?
N2 N3 N4 109.7(4) . . ?
N2 N3 Cu4 123.0(3) . . ?
N4 N3 Cu4 126.4(3) . . ?
N11 N10 N9 108.8(4) . . ?
N11 N10 Na1 121.0(3) . 2_666 ?
N9 N10 Na1 126.4(3) . 2_666 ?
N5 C4 N8 110.8(4) . . ?
N5 C4 C3 124.6(4) . . ?
N8 C4 C3 124.6(4) . . ?
C8 N9 N10 105.5(4) . . ?
C8 N9 Na1 123.9(3) . . ?
N10 N9 Na1 126.5(3) . . ?
N19 C11 N21 112.3(4) . . ?
N19 C11 C49 123.1(4) . . ?
N21 C11 C49 124.6(5) . . ?
N13 C6 N16 111.2(4) . . ?
N13 C6 C5 125.0(4) . . ?
N16 C6 C5 123.8(4) . . ?
N3 N2 N1 108.7(4) . . ?
N3 N2 Na1 101.0(3) . 2_656 ?
N1 N2 Na1 116.4(3) . 2_656 ?
N1 C2 N4 110.6(5) . . ?
N1 C2 C1 124.6(5) . . ?
N4 C2 C1 124.9(5) . . ?
N9 C8 N12 112.0(4) . . ?
N9 C8 C7 125.5(5) . . ?
N12 C8 C7 122.4(5) . . ?
C2 N1 N2 106.1(4) . . ?
C2 N1 Na1 139.4(4) . 1_645 ?
N2 N1 Na1 111.2(3) . 1_645 ?
N17 C10 C9 178.4(9) . . ?
C10 N17 Na1 166.0(7) . . ?
N10 Na1 N1 117.03(18) 2_666 1_465 ?
N10 Na1 N17 120.0(2) 2_666 . ?
N1 Na1 N17 122.5(2) 1_465 . ?
N10 Na1 N9 96.45(15) 2_666 . ?
N1 Na1 N9 85.93(18) 1_465 . ?
N17 Na1 N9 94.5(2) . . ?
N10 Na1 N2 96.03(15) 2_666 2_656 ?
N1 Na1 N2 86.86(16) 1_465 2_656 ?
N17 Na1 N2 80.7(2) . 2_656 ?
N9 Na1 N2 167.40(16) . 2_656 ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.691
_refine_diff_density_min         -0.590
_refine_diff_density_rms         0.131
