# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1579331'
_audit_update_record             
;
2017-10-11 deposited with the CCDC.
2017-12-20 downloaded from the CCDC.
;
_audit_creation_date             2017-10-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H8 Cu2 F3 N O10'
_chemical_formula_sum            'C23 H8 Cu2 F3 N O10'
_chemical_formula_weight         642.40
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_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'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x-y, x, z+1/2'
'-y, x-y, z'
'-x, -y, z+1/2'
'-x+y, -x, z'
'y, -x+y, z+1/2'
'x-y, -y, -z'
'-x, -x+y, -z'
'y, x, -z'
'-y, -x, -z+1/2'
'-x+y, y, -z+1/2'
'x, x-y, -z+1/2'
'-x, -y, -z'
'-x+y, -x, -z-1/2'
'y, -x+y, -z'
'x, y, -z-1/2'
'x-y, x, -z'
'-y, x-y, -z-1/2'
'-x+y, y, z'
'x, x-y, z'
'-y, -x, z'
'y, x, z-1/2'
'x-y, -y, z-1/2'
'-x, -x+y, z-1/2'

_cell_length_a                   18.5000(13)
_cell_length_b                   18.5000(13)
_cell_length_c                   23.582(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     6989.8(12)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    678
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.103
_cell_measurement_theta_min      2.145
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.955
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABAS 2.10 (Bruker 2003)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Blue
_exptl_crystal_density_diffrn    0.916
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1908.0
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   0.850
_exptl_transmission_factor_min   0.786
_diffrn_reflns_av_R_equivalents  0.2225
_diffrn_reflns_av_unetI/netI     0.0743
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            54657
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.103
_diffrn_reflns_theta_max         25.103
_diffrn_reflns_theta_min         2.145
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       /w-scans
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1355
_reflns_number_total             2354
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.799
_refine_diff_density_rms         0.133
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         2349
_refine_ls_number_restraints     41
_refine_ls_R_factor_all          0.1194
_refine_ls_R_factor_gt           0.0801
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1601P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2460
_refine_ls_wR_factor_ref         0.2696
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C22) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
4. Others
 Fixed Sof: N6(0.25) C9(0.5) H9(0.5) C10(0.25) C22(0.25)
5.a Ternary CH refined with riding coordinates:
 C9(H9)
5.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.52364(3) 0.04728(6) 0.54627(5) 0.0455(5) Uani 1 2 d S TU P . .
C1 C 0.6414(4) 0.0893(4) 0.4584(3) 0.0530(17) Uani 1 1 d . U . . .
O2 O 0.6282(3) 0.1093(2) 0.5070(2) 0.0584(13) Uani 1 1 d . U . . .
C5 C 0.7785(3) 0.2215(3) 0.4567(4) 0.045(2) Uani 1 2 d S TU P . .
H5 H 0.764025 0.235974 0.490849 0.055 Uiso 1 2 calc RS T P . .
O6 O 0.5595(3) -0.0302(3) 0.57131(19) 0.0563(13) Uani 1 1 d . U . . .
C7 C 0.7487(4) 0.1244(4) 0.3813(3) 0.0545(17) Uani 1 1 d . U . . .
H7 H 0.712429 0.073912 0.363928 0.065 Uiso 1 1 calc R . . . .
C8 C 0.7247(4) 0.1459(4) 0.4312(3) 0.0491(16) Uani 1 1 d . U . . .
C11 C 0.8244(3) 0.1756(3) 0.3572(4) 0.054(2) Uani 1 2 d S TU P . .
O13 O 0.5583(3) 0.1167(6) 0.6223(3) 0.099(3) Uani 1 2 d S TU P . .
C0AA C 0.8261(4) 0.1739(4) 0.250000 0.048(3) Uani 1 4 d S TU P . .
C2 C 0.8469(3) 0.1531(3) 0.2991(5) 0.069(3) Uani 1 2 d S TU P . .
N6 N 0.7573(8) 0.1869(8) 0.250000 0.053(4) Uani 0.5 2 d S TU P . .
C9 C 0.9288(8) 0.1570(8) 0.3011(6) 0.061(3) Uani 0.5 1 d . U . . .
H9 H 0.963679 0.176462 0.335132 0.073 Uiso 0.5 1 calc R . . . .
F1 F 1.0589(4) 0.1179(8) 0.2912(4) 0.163(4) Uani 1 2 d S TU P . .
F3 F 1.1121(5) 0.2241(9) 0.250000 0.223(9) Uani 1 4 d S TU P . .
C10 C 0.9614(13) 0.1522(13) 0.250000 0.062(4) Uani 0.5 2 d S TU P . .
C22 C 1.0413(16) 0.1541(18) 0.250000 0.093(6) Uani 0.5 2 d S TU 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 Cu1 2.657(2) 13_656 ?
Cu1 O2 1.922(4) . ?
Cu1 O2 1.922(4) 19_655 ?
Cu1 O6 1.948(5) . ?
Cu1 O6 1.948(5) 19_655 ?
Cu1 O13 2.110(7) . ?
C1 O2 1.267(8) . ?
C1 O6 1.247(8) 7_556 ?
C1 C8 1.505(9) . ?
C5 C8 1.384(7) 21_665 ?
C5 C8 1.384(7) . ?
O6 C1 1.247(8) 7_556 ?
C7 C8 1.384(9) . ?
C7 C11 1.361(8) . ?
C11 C7 1.361(8) 21_665 ?
C11 C2 1.550(14) . ?
C0AA C2 1.334(13) 16_556 ?
C0AA C2 1.334(13) . ?
C0AA N6 1.410(19) . ?
C0AA N6 1.410(19) 21_665 ?
C2 C9 1.482(15) . ?
C2 C9 1.482(15) 21_665 ?
N6 N6 1.03(3) 21_665 ?
C9 C9 1.59(3) 21_665 ?
C9 C10 1.369(16) . ?
F1 C22 1.311(19) 19_755 ?
F1 C22 1.311(19) . ?
F3 C22 1.30(3) 19_755 ?
F3 C22 1.30(3) . ?
C10 C9 1.369(16) 16_556 ?
C10 C22 1.46(3) . ?
C22 F1 1.311(19) 16_556 ?
C22 C22 1.32(5) 19_755 ?

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 Cu1 84.22(14) 19_655 13_656 ?
O2 Cu1 Cu1 84.22(14) . 13_656 ?
O2 Cu1 O2 90.1(3) . 19_655 ?
O2 Cu1 O6 88.5(2) . . ?
O2 Cu1 O6 88.5(2) 19_655 19_655 ?
O2 Cu1 O6 167.66(19) 19_655 . ?
O2 Cu1 O6 167.66(19) . 19_655 ?
O2 Cu1 O13 97.9(2) . . ?
O2 Cu1 O13 97.9(2) 19_655 . ?
O6 Cu1 Cu1 83.44(14) 19_655 13_656 ?
O6 Cu1 Cu1 83.44(14) . 13_656 ?
O6 Cu1 O6 90.3(3) . 19_655 ?
O6 Cu1 O13 94.5(2) . . ?
O6 Cu1 O13 94.5(2) 19_655 . ?
O13 Cu1 Cu1 177.0(3) . 13_656 ?
O2 C1 C8 117.5(6) . . ?
O6 C1 O2 126.1(7) 7_556 . ?
O6 C1 C8 116.2(6) 7_556 . ?
C1 O2 Cu1 123.1(4) . . ?
C8 C5 C8 119.8(9) 21_665 . ?
C1 O6 Cu1 123.2(5) 7_556 . ?
C11 C7 C8 121.4(7) . . ?
C5 C8 C1 119.2(6) . . ?
C5 C8 C7 119.1(7) . . ?
C7 C8 C1 121.7(6) . . ?
C7 C11 C7 119.1(9) . 21_665 ?
C7 C11 C2 120.2(5) 21_665 . ?
C7 C11 C2 120.2(5) . . ?
C2 C0AA C2 120.3(14) . 16_556 ?
C2 C0AA N6 117.6(6) 16_556 . ?
C2 C0AA N6 117.6(6) 16_556 21_665 ?
C2 C0AA N6 117.6(6) . 21_665 ?
C2 C0AA N6 117.6(6) . . ?
N6 C0AA N6 42.9(11) . 21_665 ?
C0AA C2 C11 122.4(10) . . ?
C0AA C2 C9 116.6(10) . . ?
C0AA C2 C9 116.6(10) . 21_665 ?
C9 C2 C11 111.4(9) 21_665 . ?
C9 C2 C11 111.4(9) . . ?
C9 C2 C9 64.7(11) . 21_665 ?
N6 N6 C0AA 68.6(6) 21_665 . ?
C2 C9 C9 57.7(6) . 21_665 ?
C10 C9 C2 116.3(14) . . ?
C10 C9 C9 100.9(11) . 21_665 ?
C22 F1 C22 61(2) . 19_755 ?
C22 F3 C22 61(3) 19_755 . ?
C9 C10 C9 123(2) . 16_556 ?
C9 C10 C22 118.2(10) 16_556 . ?
C9 C10 C22 118.2(10) . . ?
F1 C22 F1 96(2) . 16_556 ?
F1 C22 C10 119.7(14) 16_556 . ?
F1 C22 C10 119.7(14) . . ?
F1 C22 C22 59.7(11) . 19_755 ?
F1 C22 C22 59.7(11) 16_556 19_755 ?
F3 C22 F1 97.1(16) . . ?
F3 C22 F1 97.1(16) . 16_556 ?
F3 C22 C10 122(2) . . ?
F3 C22 C22 59.5(13) . 19_755 ?
C22 C22 C10 178.8(14) 19_755 . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.769 -0.725 -0.831 4193.5 1491.6 ?

_olex2_submission_special_instructions 'No special instructions were received'
