# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1483155'
_audit_update_record             
;
2016-08-13 deposited with the CCDC.
2016-08-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H12 Cu2 N0 O10 Si'
_chemical_formula_weight         543.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           194
_space_group_name_H-M_alt        'P 63/m m c'
_space_group_name_Hall           '-P 6c 2c'

_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'
'-x, -y, z+1/2'
'y, -x+y, z+1/2'
'x-y, x, z+1/2'
'y, x, -z'
'x-y, -y, -z'
'-x, -x+y, -z'
'-y, -x, -z+1/2'
'-x+y, y, -z+1/2'
'x, x-y, -z+1/2'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'x, y, -z-1/2'
'-y, x-y, -z-1/2'
'-x+y, -x, -z-1/2'
'-y, -x, z'
'-x+y, y, z'
'x, x-y, z'
'y, x, z-1/2'
'x-y, -y, z-1/2'
'-x, -x+y, z-1/2'

_cell_length_a                   18.5185(5)
_cell_length_b                   18.5185(5)
_cell_length_c                   19.1215(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     5678.9(4)
_cell_formula_units_Z            6
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3954
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      21.82

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.953
_exptl_crystal_F_000             1632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.184
_shelx_estimated_absorpt_T_min   0.815
_shelx_estimated_absorpt_T_max   0.871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6686
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34876
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_av_R_equivalents  0.0735
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.657
_diffrn_reflns_theta_max         26.057
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2125
_reflns_number_gt                1683
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0526P)²+11.7071P] 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         2125
_refine_ls_number_parameters     80
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1278
_refine_ls_wR_factor_gt          0.1199
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_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_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 0.47642(2) -0.04716(3) 0.05626(3) 0.0375(2) Uani 1 2 d S T P . .
Si1 Si 0.26565(13) 0.13282(6) 0.2500 0.0513(5) Uani 1 4 d S T P . .
O1 O 0.43949(16) 0.02918(14) 0.08988(13) 0.0520(6) Uani 1 1 d . . . . .
O2 O 0.48069(16) 0.10963(14) -0.00534(14) 0.0542(7) Uani 1 1 d . . . . .
O3 O 0.43801(17) -0.1240(3) 0.1473(3) 0.1068(18) Uani 1 2 d S T P . .
C3 C 0.3644(2) 0.1179(2) 0.14211(18) 0.0448(8) Uani 1 1 d . . . . .
H3 H 0.3469 0.0646 0.1619 0.054 Uiso 1 1 calc R U . . .
C4 C 0.3360(3) 0.16799(14) 0.1709(3) 0.0437(11) Uani 1 2 d S T P . .
C5 C 0.1992(4) 0.1828(4) 0.2500 0.0750(18) Uani 1 2 d S T P . .
H5A H 0.2349 0.2436 0.2500 0.112 Uiso 1 2 calc R U P . .
H5B H 0.1639 0.1655 0.2082 0.112 Uiso 0.5 1 calc R U P . .
H5C H 0.1639 0.1655 0.2918 0.112 Uiso 0.5 1 calc R U P . .
C2 C 0.4179(2) 0.14437(19) 0.08494(18) 0.0427(8) Uani 1 1 d . . . . .
C6 C 0.4429(3) 0.22143(15) 0.0561(3) 0.0443(11) Uani 1 2 d S T P . .
H6 H 0.4776 0.2388 0.0159 0.053 Uiso 1 2 calc R U P . .
C1 C 0.4485(2) 0.0900(2) 0.05402(18) 0.0440(8) 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 O2 1.959(2) 13_655 ?
Cu1 O2 1.959(2) 8 ?
Cu1 O1 1.961(2) 20_655 ?
Cu1 O1 1.961(2) . ?
Cu1 O3 2.133(4) . ?
Cu1 Cu1 2.6301(10) 13_655 ?
Si1 C5 1.874(6) . ?
Si1 C5 1.874(6) 21 ?
Si1 C4 1.887(5) . ?
Si1 C4 1.887(5) 16_556 ?
O1 C1 1.257(4) . ?
O2 C1 1.249(4) . ?
O2 Cu1 1.959(2) 13_655 ?
C3 C4 1.387(4) . ?
C3 C2 1.390(5) . ?
C3 H3 0.9500 . ?
C4 C3 1.387(4) 21 ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C2 C6 1.377(4) . ?
C2 C1 1.501(5) . ?
C6 C2 1.377(4) 21 ?
C6 H6 0.9500 . ?

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 88.99(15) 13_655 8 ?
O2 Cu1 O1 89.16(11) 13_655 20_655 ?
O2 Cu1 O1 168.31(10) 8 20_655 ?
O2 Cu1 O1 168.32(10) 13_655 . ?
O2 Cu1 O1 89.16(11) 8 . ?
O1 Cu1 O1 90.32(15) 20_655 . ?
O2 Cu1 O3 96.34(14) 13_655 . ?
O2 Cu1 O3 96.34(14) 8 . ?
O1 Cu1 O3 95.33(14) 20_655 . ?
O1 Cu1 O3 95.33(14) . . ?
O2 Cu1 Cu1 83.54(8) 13_655 13_655 ?
O2 Cu1 Cu1 83.54(8) 8 13_655 ?
O1 Cu1 Cu1 84.78(7) 20_655 13_655 ?
O1 Cu1 Cu1 84.79(7) . 13_655 ?
O3 Cu1 Cu1 179.84(15) . 13_655 ?
C5 Si1 C5 110.6(4) . 21 ?
C5 Si1 C4 109.88(13) . . ?
C5 Si1 C4 109.88(13) 21 . ?
C5 Si1 C4 109.88(13) . 16_556 ?
C5 Si1 C4 109.88(13) 21 16_556 ?
C4 Si1 C4 106.6(3) . 16_556 ?
C1 O1 Cu1 122.0(2) . . ?
C1 O2 Cu1 123.8(2) . 13_655 ?
C4 C3 C2 121.2(3) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C3 118.1(5) 21 . ?
C3 C4 Si1 120.9(2) 21 . ?
C3 C4 Si1 120.9(2) . . ?
Si1 C5 H5A 109.5 . . ?
Si1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
Si1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C6 C2 C3 119.4(3) . . ?
C6 C2 C1 119.6(3) . . ?
C3 C2 C1 121.0(3) . . ?
C2 C6 C2 120.6(5) 21 . ?
C2 C6 H6 119.7 21 . ?
C2 C6 H6 119.7 . . ?
O2 C1 O1 125.9(3) . . ?
O2 C1 C2 116.7(3) . . ?
O1 C1 C2 117.4(3) . . ?

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
C2 C3 C4 C3 -1.8(6) . . . 21 ?
C2 C3 C4 Si1 -178.3(3) . . . . ?
C5 Si1 C4 C3 30.8(4) . . . 21 ?
C5 Si1 C4 C3 152.7(4) 21 . . 21 ?
C4 Si1 C4 C3 -88.2(3) 16_556 . . 21 ?
C5 Si1 C4 C3 -152.7(4) . . . . ?
C5 Si1 C4 C3 -30.8(4) 21 . . . ?
C4 Si1 C4 C3 88.2(3) 16_556 . . . ?
C4 C3 C2 C6 -0.3(5) . . . . ?
C4 C3 C2 C1 180.0(3) . . . . ?
C3 C2 C6 C2 2.5(7) . . . 21 ?
C1 C2 C6 C2 -177.8(3) . . . 21 ?
Cu1 O2 C1 O1 0.8(5) 13_655 . . . ?
Cu1 O2 C1 C2 -179.2(2) 13_655 . . . ?
Cu1 O1 C1 O2 0.0(5) . . . . ?
Cu1 O1 C1 C2 180.0(2) . . . . ?
C6 C2 C1 O2 -14.9(5) . . . . ?
C3 C2 C1 O2 164.8(3) . . . . ?
C6 C2 C1 O1 165.1(4) . . . . ?
C3 C2 C1 O1 -15.2(5) . . . . ?

_refine_diff_density_max         0.385
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.061



