# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_8_sq
_database_code_depnum_ccdc_archive 'CCDC 1406816'
_audit_update_record             
;
2015-06-15 deposited with the CCDC.
2015-09-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ZJU-8
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H8 Cu2 N O10'
_chemical_formula_weight         573.37

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      trigonal
_space_group_IT_number           166
_space_group_name_H-M_alt        'R -3 m :H'
_space_group_name_Hall           '-R 3 2"'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z'
'-x, -x+y, -z'
'x-y, -y, -z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+1/3'
'-x+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, -y+1/3, -z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+2/3'
'-x+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, -y+2/3, -z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z'
'x, x-y, z'
'-x+y, y, z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z+1/3'
'x+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, y+1/3, z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+2/3'
'x+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, y+2/3, z+2/3'

_cell_length_a                   18.639(4)
_cell_length_b                   18.639(4)
_cell_length_c                   38.614(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     11618(5)
_cell_formula_units_Z            9
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.738
_exptl_crystal_F_000             2565
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.849
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42594
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_av_R_equivalents  0.1285
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_theta_min         2.185
_diffrn_reflns_theta_max         25.948
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2777
_reflns_number_gt                1927
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0737P)²+9.8750P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2777
_refine_ls_number_parameters     103
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1374
_refine_ls_wR_factor_gt          0.1222
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.52351(2) 0.47649(2) -0.02814(2) 0.0394(2) Uani 1 2 d S T P . .
O1 O 0.48144(16) 0.37127(14) -0.00330(6) 0.0589(6) Uani 1 1 d . . . . .
O1C O 0.55994(15) 0.44006(15) -0.07532(12) 0.1081(16) Uani 1 2 d S T P . .
O2B O 0.44153(16) 0.41089(14) 0.04401(6) 0.0600(7) Uani 1 1 d . . . . .
C4 C 0.4521(2) 0.3599(2) 0.02694(8) 0.0499(8) Uani 1 1 d . . . . .
C4B C 0.2679(7) 0.1791(5) 0.17738(19) 0.084(3) Uani 0.5 1 d . . P . .
C5 C 0.3866(4) 0.19330(18) 0.09515(13) 0.0637(14) Uani 1 2 d S T P . .
C6 C 0.4458(3) 0.22292(15) 0.02717(12) 0.0503(11) Uani 1 2 d S T P . .
H6 H 0.4655 0.2328 0.0045 0.060 Uiso 1 2 calc R U P . .
C8B C 0.4018(2) 0.2650(2) 0.07756(9) 0.0616(10) Uani 1 1 d . . . . .
H8B H 0.3919 0.3034 0.0887 0.074 Uiso 1 1 calc R U . . .
C10 C 0.4312(2) 0.2799(2) 0.04398(8) 0.0505(8) Uani 1 1 d . . . . .
N10 N 0.2434(12) 0.2117(12) 0.1193(5) 0.135(7) Uani 0.25 1 d . . P . .
H10A H 0.2526 0.2171 0.0973 0.162 Uiso 0.25 1 calc R U P . .
H10B H 0.2044 0.2180 0.1279 0.162 Uiso 0.25 1 calc R U P . .
C11 C 0.3590(4) 0.1795(2) 0.13207(14) 0.0697(16) Uani 1 2 d S T P . .
C6C C 0.2956(7) 0.1911(6) 0.1425(2) 0.083(3) Uani 0.5 1 d . . P . .


_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 O2B 1.959(2) 4 ?
Cu1 O2B 1.959(2) 19_665 ?
Cu1 O1 1.960(2) 22_665 ?
Cu1 O1 1.960(2) . ?
Cu1 O1C 2.169(4) . ?
Cu1 Cu1 2.6508(10) 19_665 ?
O1 C4 1.262(4) . ?
O2B C4 1.251(4) . ?
O2B Cu1 1.959(2) 19_665 ?
C4 C10 1.492(4) . ?
C4B C11 1.403(10) 25 ?
C4B C6C 1.418(10) . ?
C4B C4B 1.681(15) 23 ?
C4B C6C 1.744(14) 11 ?
C5 C8B 1.396(4) . ?
C5 C8B 1.396(4) 23 ?
C5 C11 1.494(7) . ?
C6 C10 1.383(4) . ?
C6 C10 1.383(4) 23 ?
C6 H6 0.9300 . ?
C8B C10 1.381(4) . ?
C8B H8B 0.9300 . ?
N10 C6C 1.51(2) . ?
N10 H10A 0.8600 . ?
N10 H10B 0.8600 . ?
C11 C6C 1.365(10) 23 ?
C11 C6C 1.365(10) . ?
C11 C4B 1.403(10) 25 ?
C11 C4B 1.403(10) 11 ?
C6C C6C 1.614(17) 23 ?
C6C C4B 1.744(14) 11 ?

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
O2B Cu1 O2B 89.17(16) 4 19_665 ?
O2B Cu1 O1 167.76(9) 4 22_665 ?
O2B Cu1 O1 89.67(11) 19_665 22_665 ?
O2B Cu1 O1 89.67(11) 4 . ?
O2B Cu1 O1 167.76(9) 19_665 . ?
O1 Cu1 O1 88.89(15) 22_665 . ?
O2B Cu1 O1C 94.82(12) 4 . ?
O2B Cu1 O1C 94.82(12) 19_665 . ?
O1 Cu1 O1C 97.42(12) 22_665 . ?
O1 Cu1 O1C 97.42(12) . . ?
O2B Cu1 Cu1 83.69(7) 4 19_665 ?
O2B Cu1 Cu1 83.69(7) 19_665 19_665 ?
O1 Cu1 Cu1 84.08(7) 22_665 19_665 ?
O1 Cu1 Cu1 84.08(7) . 19_665 ?
O1C Cu1 Cu1 177.89(15) . 19_665 ?
C4 O1 Cu1 122.9(2) . . ?
C4 O2B Cu1 123.7(2) . 19_665 ?
O2B C4 O1 125.5(3) . . ?
O2B C4 C10 117.7(3) . . ?
O1 C4 C10 116.8(3) . . ?
C11 C4B C6C 117.8(8) 25 . ?
C11 C4B C4B 53.2(4) 25 23 ?
C6C C4B C4B 88.7(5) . 23 ?
C11 C4B C6C 50.0(5) 25 11 ?
C6C C4B C6C 88.9(8) . 11 ?
C4B C4B C6C 88.9(4) 23 11 ?
C8B C5 C8B 117.7(4) . 23 ?
C8B C5 C11 121.1(2) . . ?
C8B C5 C11 121.1(2) 23 . ?
C10 C6 C10 120.1(4) . 23 ?
C10 C6 H6 120.0 . . ?
C10 C6 H6 120.0 23 . ?
C10 C8B C5 121.3(3) . . ?
C10 C8B H8B 119.3 . . ?
C5 C8B H8B 119.3 . . ?
C8B C10 C6 119.8(3) . . ?
C8B C10 C4 119.6(3) . . ?
C6 C10 C4 120.5(3) . . ?
C6C N10 H10A 120.0 . . ?
C6C N10 H10B 120.0 . . ?
H10A N10 H10B 120.0 . . ?
C6C C11 C6C 72.5(8) 23 . ?
C6C C11 C4B 78.1(6) 23 25 ?
C6C C11 C4B 120.2(6) . 25 ?
C6C C11 C4B 120.2(6) 23 11 ?
C6C C11 C4B 78.1(6) . 11 ?
C4B C11 C4B 73.6(8) 25 11 ?
C6C C11 C5 120.4(5) 23 . ?
C6C C11 C5 120.4(5) . . ?
C4B C11 C5 119.4(5) 25 . ?
C4B C11 C5 119.4(5) 11 . ?
C11 C6C C4B 122.0(8) . . ?
C11 C6C N10 125.8(10) . . ?
C4B C6C N10 112.1(11) . . ?
C11 C6C C6C 53.7(4) . 23 ?
C4B C6C C6C 91.4(5) . 23 ?
N10 C6C C6C 125.3(9) . 23 ?
C11 C6C C4B 51.9(5) . 11 ?
C4B C6C C4B 91.0(8) . 11 ?
N10 C6C C4B 134.4(10) . 11 ?
C6C C6C C4B 91.1(4) 23 11 ?

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
Cu1 O2B C4 O1 -4.7(5) 19_665 . . . ?
Cu1 O2B C4 C10 173.1(2) 19_665 . . . ?
Cu1 O1 C4 O2B 4.4(5) . . . . ?
Cu1 O1 C4 C10 -173.4(2) . . . . ?
C8B C5 C8B C10 -0.4(8) 23 . . . ?
C11 C5 C8B C10 176.8(5) . . . . ?
C5 C8B C10 C6 0.3(7) . . . . ?
C5 C8B C10 C4 -175.8(4) . . . . ?
C10 C6 C10 C8B -0.2(7) 23 . . . ?
C10 C6 C10 C4 175.9(3) 23 . . . ?
O2B C4 C10 C8B -0.4(5) . . . . ?
O1 C4 C10 C8B 177.6(3) . . . . ?
O2B C4 C10 C6 -176.4(4) . . . . ?
O1 C4 C10 C6 1.5(5) . . . . ?
C8B C5 C11 C6C 134.8(7) . . . 23 ?
C8B C5 C11 C6C -48.2(9) 23 . . 23 ?
C8B C5 C11 C6C 48.2(9) . . . . ?
C8B C5 C11 C6C -134.8(7) 23 . . . ?
C8B C5 C11 C4B -132.0(6) . . . 25 ?
C8B C5 C11 C4B 45.0(9) 23 . . 25 ?
C8B C5 C11 C4B -45.0(9) . . . 11 ?
C8B C5 C11 C4B 132.0(6) 23 . . 11 ?
C6C C11 C6C C4B 64.9(12) 23 . . . ?
C4B C11 C6C C4B 0.5(15) 25 . . . ?
C4B C11 C6C C4B -62.3(9) 11 . . . ?
C5 C11 C6C C4B -179.6(8) . . . . ?
C6C C11 C6C N10 -110.7(12) 23 . . . ?
C4B C11 C6C N10 -175.1(12) 25 . . . ?
C4B C11 C6C N10 122.0(13) 11 . . . ?
C5 C11 C6C N10 4.8(15) . . . . ?
C4B C11 C6C C6C -64.4(6) 25 . . 23 ?
C4B C11 C6C C6C -127.2(5) 11 . . 23 ?
C5 C11 C6C C6C 115.5(7) . . . 23 ?
C6C C11 C6C C4B 127.2(5) 23 . . 11 ?
C4B C11 C6C C4B 62.9(8) 25 . . 11 ?
C5 C11 C6C C4B -117.3(5) . . . 11 ?
C11 C4B C6C C11 -0.5(15) 25 . . . ?
C4B C4B C6C C11 -46.9(8) 23 . . . ?
C6C C4B C6C C11 42.0(11) 11 . . . ?
C11 C4B C6C N10 175.6(10) 25 . . . ?
C4B C4B C6C N10 129.2(11) 23 . . . ?
C6C C4B C6C N10 -141.8(10) 11 . . . ?
C11 C4B C6C C6C 46.4(8) 25 . . 23 ?
C4B C4B C6C C6C 0.006(2) 23 . . 23 ?
C6C C4B C6C C6C 88.9(4) 11 . . 23 ?
C11 C4B C6C C4B -44.7(10) 25 . . 11 ?
C4B C4B C6C C4B -91.1(4) 23 . . 11 ?
C6C C4B C6C C4B -2.2(8) 11 . . 11 ?

_refine_diff_density_max         0.554
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.060

_shelxl_version_number           2014/6




