# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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. 
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data_CFA-14
_database_code_depnum_ccdc_archive 'CCDC 1811523'
_audit_update_record             
;
2018-07-10 deposited with the CCDC.
2018-08-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H6 Co2 F12 N4 O2'
_chemical_formula_sum            'C16 H6 Co2 F12 N4 O2'
_chemical_formula_weight         632.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0041 0.0020 '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'
F F 0.0215 0.0127 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0078 0.0041 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3468 1.1590 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0135 0.0075 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           142
_space_group_name_H-M_alt        'I 41/a c d'
_space_group_name_Hall           '-I 4bd 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'
'-x+1/2, -y, z+1/2'
'-y+1/4, x+3/4, z+1/4'
'y+1/4, -x+1/4, z+3/4'
'-x+1/2, y, -z'
'x, -y, -z+1/2'
'y+1/4, x+3/4, -z+3/4'
'-y+1/4, -x+1/4, -z+1/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+3/4, x+5/4, z+3/4'
'y+3/4, -x+3/4, z+5/4'
'-x+1, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1'
'y+3/4, x+5/4, -z+5/4'
'-y+3/4, -x+3/4, -z+3/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-1/4, -x-3/4, -z-1/4'
'-y-1/4, x-1/4, -z-3/4'
'x-1/2, -y, z'
'-x, y, z-1/2'
'-y-1/4, -x-3/4, z-3/4'
'y-1/4, x-1/4, z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y+1/4, -x-1/4, -z+1/4'
'-y+1/4, x+1/4, -z-1/4'
'x, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z'
'-y+1/4, -x-1/4, z-1/4'
'y+1/4, x+1/4, z+1/4'

_cell_length_a                   20.3213(11)
_cell_length_b                   20.3213(11)
_cell_length_c                   12.4045(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5122.5(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8073
_cell_measurement_theta_min      1.54
_cell_measurement_theta_max      27.895

_exptl_crystal_description       'block crystal'
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_F_000             2464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.070
_exptl_crystal_size_mid          0.015
_exptl_crystal_size_min          0.007
_exptl_absorpt_coefficient_mu    1.809
_shelx_estimated_absorpt_T_min   0.884
_shelx_estimated_absorpt_T_max   0.987
_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      100(2)
_diffrn_radiation_wavelength     0.78201
_diffrn_radiation_type           Synchrotron
_diffrn_source                   'SPring-8 BL40XU'
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16392
_diffrn_reflns_av_unetI/netI     0.1000
_diffrn_reflns_av_R_equivalents  0.1739
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.370
_diffrn_reflns_theta_max         28.082
_diffrn_reflns_theta_full        27.983
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             1170
_reflns_number_gt                626
_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.
 
 _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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Diamond 4.4'
_computing_publication_material  Word
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1170
_refine_ls_number_parameters     87
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1760
_refine_ls_R_factor_gt           0.1254
_refine_ls_wR_factor_ref         0.3677
_refine_ls_wR_factor_gt          0.3349
_refine_ls_goodness_of_fit_ref   1.210
_refine_ls_restrained_S_all      1.208
_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
Co1 Co 0.250000 0.47284(10) 0.500000 0.0940(12) Uani 1 2 d S T P . .
O1 O 0.2727(4) 0.5227(4) 0.625000 0.112(4) Uani 1 2 d DS T P . .
N1 N 0.1814(4) 0.4163(4) 0.5719(6) 0.090(2) Uani 1 1 d . . . . .
C1 C 0.1402(5) 0.3707(5) 0.5421(8) 0.100(3) Uani 1 1 d . . . . .
C3 C 0.0495(6) 0.2995(6) 0.625000 0.110(5) Uani 1 2 d S T P . .
C2 C 0.1001(5) 0.3501(5) 0.625000 0.102(4) Uani 1 2 d S T P . .
C4 C 0.0680(8) 0.2313(7) 0.62509(16) 0.154(6) Uani 1 1 d . . . . .
H4 H 0.113182 0.219233 0.625277 0.185 Uiso 1 1 calc R U . . .
C5 C 0.1421(9) 0.3438(9) 0.4293(12) 0.145(5) Uani 1 1 d . . . . .
H1 H 0.3049(8) 0.5549(8) 0.625000 0.21(11) Uiso 1 2 d DS . P . .
F1 F 0.1764(6) 0.3801(5) 0.3637(6) 0.204(5) Uani 1 1 d . . . . .
F2 F 0.0893(5) 0.3219(6) 0.3914(6) 0.181(4) Uani 1 1 d . . . . .
F3 F 0.1768(8) 0.2879(7) 0.4249(10) 0.233(6) 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
Co1 O1 1.910(6) 11_544 ?
Co1 O1 1.910(6) . ?
Co1 N1 2.014(7) 5_556 ?
Co1 N1 2.015(7) . ?
O1 H1 0.93(2) . ?
N1 C1 1.302(12) . ?
N1 N1 1.387(15) 15_445 ?
C1 C2 1.379(13) . ?
C1 C5 1.503(18) . ?
C3 C4 1.437(16) 15_445 ?
C3 C4 1.437(16) . ?
C3 C2 1.45(2) . ?
C4 C4 1.42(3) 8_556 ?
C4 H4 0.9500 . ?
C5 F2 1.251(15) . ?
C5 F1 1.301(15) . ?
C5 F3 1.34(2) . ?

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
O1 Co1 O1 115.8(3) 11_544 . ?
O1 Co1 N1 96.4(3) 11_544 5_556 ?
O1 Co1 N1 119.7(2) . 5_556 ?
O1 Co1 N1 119.7(2) 11_544 . ?
O1 Co1 N1 96.4(3) . . ?
N1 Co1 N1 110.5(5) 5_556 . ?
Co1 O1 Co1 113.7(5) . 12_454 ?
Co1 O1 H1 123.1(3) . . ?
Co1 O1 H1 123.1(3) 12_454 . ?
C1 N1 N1 106.6(5) . 15_445 ?
C1 N1 Co1 136.4(6) . . ?
N1 N1 Co1 116.6(2) 15_445 . ?
N1 C1 C2 112.7(9) . . ?
N1 C1 C5 120.5(9) . . ?
C2 C1 C5 126.7(10) . . ?
C4 C3 C4 120.3(19) 15_445 . ?
C4 C3 C2 119.9(10) 15_445 . ?
C4 C3 C2 119.9(10) . . ?
C1 C2 C1 101.3(12) . 15_445 ?
C1 C2 C3 129.4(6) . . ?
C1 C2 C3 129.4(6) 15_445 . ?
C4 C4 C3 119.9(10) 8_556 . ?
C4 C4 H4 120.1 8_556 . ?
C3 C4 H4 120.1 . . ?
F2 C5 F1 115.2(15) . . ?
F2 C5 F3 97.8(13) . . ?
F1 C5 F3 100.0(14) . . ?
F2 C5 C1 117.2(13) . . ?
F1 C5 C1 112.8(11) . . ?
F3 C5 C1 111.1(15) . . ?

_refine_diff_density_max         0.940
_refine_diff_density_min         -0.704
_refine_diff_density_rms         0.129

