# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
'Jinhee Park'
'Jian-Rong Li'
'Ying-Pin Chen'
'Linbing Sun'
'Hong-Cai Zhou'
_publ_contact_author_name        'Ying-Pin Chen'
_publ_contact_author_email       ying-pin.chen@mail.chem.tamu.edu

data_cubici_sq
_database_code_depnum_ccdc_archive 'CCDC 858820'
#TrackingRef '- cubici_sq_final.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H11 Cu2 N3 O11'
_chemical_formula_sum            'C23 H11 Cu2 N3 O11'
_chemical_formula_weight         632.43

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'
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'
Cu Cu 0.3201 1.2651 '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'

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

_cell_length_a                   30.585(12)
_cell_length_b                   30.585(12)
_cell_length_c                   30.585(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     28611(19)
_cell_formula_units_Z            24
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    9919
_cell_measurement_theta_min      2.307
_cell_measurement_theta_max      21.644

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    0.881
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             7584
_exptl_absorpt_coefficient_mu    0.927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9049
_exptl_absorpt_correction_T_max  0.9380
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      110(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  'Bruker SMART APEX II CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            180466
_diffrn_reflns_av_R_equivalents  0.1305
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         28.70
_reflns_number_total             3484
_reflns_number_gt                2829
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT+ ver. (Bruker, 2001)'
_computing_data_reduction        'SAINT+ ver. (Bruker, 2001)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0520P)^2^+300.0000P] where P=(Fo^2^+2Fc^2^)/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         3484
_refine_ls_number_parameters     93
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1186
_refine_ls_R_factor_gt           0.0914
_refine_ls_wR_factor_ref         0.2125
_refine_ls_wR_factor_gt          0.1966
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_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 0.18402(2) 0.18402(2) 0.0000 0.0381(3) Uani 1 4 d S . .
Cu2 Cu 0.5000 0.25497(2) 0.25497(2) 0.0404(3) Uani 1 4 d S . .
O1 O 0.27236(12) 0.20895(12) 0.04484(13) 0.0604(10) Uani 1 1 d . . .
O1S O 0.13450(19) 0.13450(19) 0.0000 0.116(4) Uani 1 4 d S . .
O2 O 0.22016(11) 0.15729(11) 0.04498(12) 0.0560(9) Uani 1 1 d . . .
O3 O 0.4146(3) 0.1642(4) 0.0813(3) 0.0924(16) Uani 0.50 1 d P . .
N1 N 0.5000 0.2055(3) 0.2055(3) 0.0924(16) Uani 1 4 d SD . .
N2 N 0.3859(2) 0.15190(19) 0.15190(19) 0.0924(16) Uani 1 2 d S . .
H2A H 0.3926 0.1520 0.1805 0.111 Uiso 0.50 1 d PR . .
C1 C 0.25534(17) 0.17408(17) 0.05872(15) 0.0487(11) Uani 1 1 d . . .
C2 C 0.2580(2) 0.11520(16) 0.11520(16) 0.0447(15) Uani 1 2 d S . .
H2B H 0.2297 0.1056 0.1056 0.054 Uiso 1 2 d SR . .
C3 C 0.27847(16) 0.14981(18) 0.09450(17) 0.0524(12) Uani 1 1 d . . .
C4 C 0.3206(2) 0.1621(2) 0.1063(2) 0.0723(17) Uani 1 1 d . . .
H4A H 0.3345 0.1863 0.0921 0.087 Uiso 1 1 d R . .
C5 C 0.3415(3) 0.1394(2) 0.1394(2) 0.077(3) Uani 1 2 d S . .
C6 C 0.4180(4) 0.1629(6) 0.1221(4) 0.0924(16) Uani 0.50 1 d P . .
C7 C 0.4631(3) 0.1965(5) 0.1844(4) 0.0924(16) Uani 0.50 1 d PD . .
H7A H 0.4361 0.2027 0.2027 0.111 Uiso 1 2 d SR . .
C8 C 0.4614(4) 0.1758(5) 0.1435(4) 0.0924(16) Uani 0.50 1 d PD . .
C9 C 0.5000 0.1636(8) 0.1238(6) 0.0924(16) Uani 0.50 2 d SPD . .
H9A H 0.5000 0.1508 0.0951 0.111 Uiso 0.50 2 d SPR . .

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 0.0361(4) 0.0361(4) 0.0421(6) 0.000 0.000 -0.0115(4)
Cu2 0.0423(6) 0.0394(4) 0.0394(4) -0.0139(5) 0.000 0.000
O1 0.057(2) 0.055(2) 0.069(2) 0.0193(18) -0.0112(18) -0.0217(17)
O1S 0.080(5) 0.080(5) 0.187(12) 0.000 0.000 -0.054(6)
O2 0.055(2) 0.051(2) 0.062(2) 0.0164(17) -0.0152(17) -0.0175(17)
O3 0.049(2) 0.159(5) 0.070(3) -0.032(3) -0.011(2) -0.010(3)
N1 0.049(2) 0.159(5) 0.070(3) -0.032(3) -0.011(2) -0.010(3)
N2 0.049(2) 0.159(5) 0.070(3) -0.032(3) -0.011(2) -0.010(3)
C1 0.051(3) 0.053(3) 0.042(2) 0.007(2) -0.002(2) -0.004(2)
C2 0.041(3) 0.047(2) 0.047(2) 0.002(3) -0.006(2) -0.006(2)
C3 0.044(3) 0.060(3) 0.053(3) 0.012(2) -0.009(2) -0.009(2)
C4 0.061(3) 0.072(4) 0.083(4) 0.023(3) -0.022(3) -0.019(3)
C5 0.058(5) 0.087(4) 0.087(4) 0.018(5) -0.022(4) -0.022(4)
C6 0.049(2) 0.159(5) 0.070(3) -0.032(3) -0.011(2) -0.010(3)
C7 0.049(2) 0.159(5) 0.070(3) -0.032(3) -0.011(2) -0.010(3)
C8 0.049(2) 0.159(5) 0.070(3) -0.032(3) -0.011(2) -0.010(3)
C9 0.049(2) 0.159(5) 0.070(3) -0.032(3) -0.011(2) -0.010(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 1.945(3) 62 ?
Cu1 O2 1.945(3) 13 ?
Cu1 O2 1.945(3) 50 ?
Cu1 O2 1.945(3) . ?
Cu1 O1S 2.142(8) . ?
Cu1 Cu2 2.6391(17) 81 ?
Cu2 O1 1.949(4) 95 ?
Cu2 O1 1.949(4) 30 ?
Cu2 O1 1.949(4) 77 ?
Cu2 O1 1.949(4) 48 ?
Cu2 N1 2.139(12) . ?
Cu2 Cu1 2.6390(17) 77 ?
O1 C1 1.261(6) . ?
O1 Cu2 1.949(4) 81 ?
O2 C1 1.264(6) . ?
O3 C6 1.253(15) . ?
N1 C7 1.328(11) 67 ?
N1 C7 1.328(11) 52_655 ?
N1 C7 1.328(11) 18_655 ?
N1 C7 1.328(11) . ?
N2 C6 1.381(14) 67 ?
N2 C6 1.381(14) . ?
N2 C5 1.461(10) . ?
N2 H2A 0.8975 . ?
C1 C3 1.500(7) . ?
C2 C3 1.383(6) 67 ?
C2 C3 1.383(6) . ?
C2 H2B 0.9600 . ?
C3 C4 1.389(7) . ?
C4 C5 1.383(7) . ?
C4 H4A 0.9600 . ?
C5 C4 1.383(7) 67 ?
C6 C8 1.530(16) . ?
C6 C6 1.76(3) 67 ?
C7 C7 0.52(4) 67 ?
C7 C8 1.407(16) . ?
C7 C8 1.646(19) 67 ?
C7 H7A 1.0148 . ?
C8 C9 1.376(16) . ?
C8 C8 1.40(3) 67 ?
C8 C7 1.646(19) 67 ?
C9 C8 1.377(16) 52_655 ?
C9 C9 1.72(4) 18_655 ?
C9 H9A 0.9600 . ?

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 90.0(2) 62 13 ?
O2 Cu1 O2 168.0(2) 62 50 ?
O2 Cu1 O2 88.7(2) 13 50 ?
O2 Cu1 O2 88.7(2) 62 . ?
O2 Cu1 O2 168.0(2) 13 . ?
O2 Cu1 O2 90.0(2) 50 . ?
O2 Cu1 O1S 96.00(10) 62 . ?
O2 Cu1 O1S 96.00(10) 13 . ?
O2 Cu1 O1S 96.00(10) 50 . ?
O2 Cu1 O1S 96.01(10) . . ?
O2 Cu1 Cu2 84.00(10) 62 81 ?
O2 Cu1 Cu2 84.00(10) 13 81 ?
O2 Cu1 Cu2 84.00(10) 50 81 ?
O2 Cu1 Cu2 83.99(10) . 81 ?
O1S Cu1 Cu2 180.0(2) . 81 ?
O1 Cu2 O1 89.5(2) 95 30 ?
O1 Cu2 O1 168.9(2) 95 77 ?
O1 Cu2 O1 89.5(2) 30 77 ?
O1 Cu2 O1 89.5(2) 95 48 ?
O1 Cu2 O1 168.9(2) 30 48 ?
O1 Cu2 O1 89.5(2) 77 48 ?
O1 Cu2 N1 95.57(10) 95 . ?
O1 Cu2 N1 95.57(10) 30 . ?
O1 Cu2 N1 95.57(10) 77 . ?
O1 Cu2 N1 95.57(10) 48 . ?
O1 Cu2 Cu1 84.43(10) 95 77 ?
O1 Cu2 Cu1 84.43(10) 30 77 ?
O1 Cu2 Cu1 84.43(10) 77 77 ?
O1 Cu2 Cu1 84.43(10) 48 77 ?
N1 Cu2 Cu1 180.0(3) . 77 ?
C1 O1 Cu2 122.6(3) . 81 ?
C1 O2 Cu1 123.2(3) . . ?
C7 N1 C7 121.4(14) 67 52_655 ?
C7 N1 C7 116.3(13) 67 18_655 ?
C7 N1 C7 22.7(15) 52_655 18_655 ?
C7 N1 C7 22.7(15) 67 . ?
C7 N1 C7 116.3(13) 52_655 . ?
C7 N1 C7 121.4(14) 18_655 . ?
C7 N1 Cu2 119.3(7) 67 . ?
C7 N1 Cu2 119.3(7) 52_655 . ?
C7 N1 Cu2 119.3(7) 18_655 . ?
C7 N1 Cu2 119.3(7) . . ?
C6 N2 C6 79.4(14) 67 . ?
C6 N2 C5 123.5(7) 67 . ?
C6 N2 C5 123.5(7) . . ?
C6 N2 H2A 66.5 67 . ?
C6 N2 H2A 118.5 . . ?
C5 N2 H2A 117.9 . . ?
O1 C1 O2 125.7(4) . . ?
O1 C1 C3 118.0(4) . . ?
O2 C1 C3 116.3(4) . . ?
C3 C2 C3 119.7(6) 67 . ?
C3 C2 H2B 120.2 67 . ?
C3 C2 H2B 120.2 . . ?
C2 C3 C4 120.5(5) . . ?
C2 C3 C1 119.9(4) . . ?
C4 C3 C1 119.6(5) . . ?
C5 C4 C3 118.9(6) . . ?
C5 C4 H4A 120.9 . . ?
C3 C4 H4A 120.2 . . ?
C4 C5 C4 121.3(8) 67 . ?
C4 C5 N2 119.3(4) 67 . ?
C4 C5 N2 119.3(4) . . ?
O3 C6 N2 127.2(11) . . ?
O3 C6 C8 119.2(12) . . ?
N2 C6 C8 113.5(11) . . ?
O3 C6 C6 136.6(10) . 67 ?
N2 C6 C6 50.3(7) . 67 ?
C8 C6 C6 83.1(8) . 67 ?
C7 C7 N1 78.6(8) 67 . ?
C7 C7 C8 108.1(8) 67 . ?
N1 C7 C8 123.9(11) . . ?
C7 C7 C8 54.3(8) 67 67 ?
N1 C7 C8 108.0(12) . 67 ?
C8 C7 C8 53.8(11) . 67 ?
C7 C7 H7A 75.1 67 . ?
N1 C7 H7A 112.7 . . ?
C8 C7 H7A 123.0 . . ?
C8 C7 H7A 104.3 67 . ?
C9 C8 C8 96.8(11) . 67 ?
C9 C8 C7 118.6(12) . . ?
C8 C8 C7 71.9(8) 67 . ?
C9 C8 C6 119.3(13) . . ?
C8 C8 C6 96.9(8) 67 . ?
C7 C8 C6 121.9(11) . . ?
C9 C8 C7 116.6(12) . 67 ?
C8 C8 C7 54.3(8) 67 67 ?
C7 C8 C7 17.6(12) . 67 ?
C6 C8 C7 119.3(10) . 67 ?
C8 C9 C8 118.2(18) . 52_655 ?
C8 C9 C9 83.2(11) . 18_655 ?
C8 C9 C9 83.2(11) 52_655 18_655 ?
C8 C9 H9A 120.6 . . ?
C8 C9 H9A 120.6 52_655 . ?
C9 C9 H9A 110.9 18_655 . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        28.70
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         1.553
_refine_diff_density_min         -0.813
_refine_diff_density_rms         0.098

# 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 -0.019 -0.039 -0.022 15960 3908 ' '
_platon_squeeze_details          
;
;

_publ_section_references         
;

Bruker (2001). SAINTP+ for NT. Data Reduction and
Correction Program v. 6.2, Bruker
AXS, Madison, Wisconsin, USA.

Bruker (2005). APEX2 software package. Bruker Molecular Analysis Research Tool,
v. 2008.4 Bruker AXS, Madison, Wisconsin, USA.

Sheldrick G.M. (2008). SADABS-2008/1, Bruker/Siemens Area Detector
Absorption Correction Program, Bruker AXS, Madison, Wisconsin, USA.

Sheldrick G.M. (2008). SHELXTL 2008/4, Structure Determination Software
Suite, Bruker AXS, Madison, Wisconsin, USA.

;