# 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_CoDMOX
_database_code_depnum_ccdc_archive 'CCDC 1535898'
_audit_update_record             
;
2017-03-03 deposited with the CCDC.
2017-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 Co F6 N2 O4'
_chemical_formula_sum            'C16 H14 Co F6 N2 O4'
_chemical_formula_weight         471.22

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'
Co Co 0.3494 0.9721 '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'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   8.500
_cell_length_b                   11.800
_cell_length_c                   19.500
_cell_angle_alpha                90.00
_cell_angle_beta                 97.20
_cell_angle_gamma                90.00
_cell_volume                     1940.4
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8175
_cell_measurement_theta_min      2.02
_cell_measurement_theta_max      26.74

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             948
_exptl_absorpt_coefficient_mu    0.965
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7904
_exptl_absorpt_correction_T_max  0.9256
_exptl_absorpt_process_details   
;
The absorption correlation (X-RED; Stoe & Cie, 2001)
was performed after optimizing the crystal shape 
using X-SHAPE (Stoe & Cie, 1999)
;
_exptl_special_details           
; 
 
;

_diffrn_ambient_temperature      293(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  'IPDS II'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 'not measured'
_diffrn_standards_number         'not measured'
_diffrn_standards_interval_count 'not measured'
_diffrn_standards_interval_time  'not measured'
_diffrn_standards_decay_%        'not measured'
_diffrn_reflns_number            17769
_diffrn_reflns_av_R_equivalents  0.0738
_diffrn_reflns_av_sigmaI/netI    0.0470
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         26.74
_reflns_number_total             4075
_reflns_number_gt                2521
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area (Stoe & CIE, 2001)'
_computing_cell_refinement       'X-Area (Stoe & CIE, 2001)'
_computing_data_reduction        'X-Area (Stoe & CIE, 2001)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0591P)²+0.0664P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       'not measured'
_refine_ls_number_reflns         4075
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1222
_refine_ls_wR_factor_gt          0.1033
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co -0.00274(5) 0.07858(4) 0.23581(2) 0.05753(16) Uani 1 1 d . . .
F1 F -0.5331(4) 0.0744(4) 0.0667(2) 0.185(2) Uani 1 1 d . . .
F2 F -0.4452(3) 0.2305(3) 0.1075(2) 0.1402(13) Uani 1 1 d . . .
F3 F -0.5419(3) 0.1161(3) 0.1694(2) 0.1369(12) Uani 1 1 d . . .
F4 F 0.3103(4) -0.0460(3) 0.43079(14) 0.1133(9) Uani 1 1 d . . .
F5 F 0.1299(3) 0.0446(3) 0.47117(12) 0.1061(9) Uani 1 1 d . . .
F6 F 0.3588(4) 0.1182(3) 0.47245(14) 0.1372(13) Uani 1 1 d . . .
O1 O -0.2213(3) 0.1092(2) 0.19804(12) 0.0664(6) Uani 1 1 d . . .
O2 O -0.0282(3) -0.1339(2) 0.06986(12) 0.0707(6) Uani 1 1 d . . .
O3 O 0.0811(3) 0.0503(2) 0.33079(12) 0.0666(6) Uani 1 1 d . . .
O4 O 0.3184(3) 0.33978(19) 0.26033(12) 0.0628(6) Uani 1 1 d . . .
N1 N 0.0220(3) -0.0466(2) 0.17025(14) 0.0567(6) Uani 1 1 d . . .
N2 N 0.1311(3) 0.2144(2) 0.22721(12) 0.0541(6) Uani 1 1 d . . .
C1 C -0.4513(5) 0.1209(4) 0.1189(3) 0.0838(12) Uani 1 1 d . . .
C2 C -0.2890(4) 0.0704(3) 0.13966(19) 0.0639(9) Uani 1 1 d . . .
C3 C -0.2309(4) -0.0049(3) 0.09753(19) 0.0662(9) Uani 1 1 d . . .
H3 H -0.2913 -0.0227 0.0558 0.079 Uiso 1 1 calc R . .
C4 C -0.0806(4) -0.0584(3) 0.11412(18) 0.0604(8) Uani 1 1 d . . .
C5 C 0.1184(4) -0.1731(3) 0.1022(2) 0.0685(9) Uani 1 1 d . . .
C6 C 0.2047(6) -0.2573(4) 0.0635(2) 0.1007(15) Uani 1 1 d . . .
H6A H 0.2290 -0.2240 0.0212 0.151 Uiso 1 1 calc R . .
H6B H 0.1393 -0.3230 0.0533 0.151 Uiso 1 1 calc R . .
H6C H 0.3013 -0.2791 0.0913 0.151 Uiso 1 1 calc R . .
C7 C 0.1481(4) -0.1209(3) 0.16248(18) 0.0609(8) Uani 1 1 d . . .
C8 C 0.2843(4) -0.1318(4) 0.2187(2) 0.0825(11) Uani 1 1 d . . .
H8A H 0.2469 -0.1615 0.2595 0.124 Uiso 1 1 calc R . .
H8B H 0.3311 -0.0587 0.2286 0.124 Uiso 1 1 calc R . .
H8C H 0.3621 -0.1822 0.2039 0.124 Uiso 1 1 calc R . .
C9 C 0.2508(5) 0.0578(4) 0.4350(2) 0.0748(10) Uani 1 1 d . . .
C10 C 0.1981(4) 0.1064(3) 0.36428(16) 0.0565(8) Uani 1 1 d . . .
C11 C 0.2753(4) 0.1979(3) 0.34394(17) 0.0628(8) Uani 1 1 d . . .
H11 H 0.3562 0.2295 0.3745 0.075 Uiso 1 1 calc R . .
C12 C 0.2379(4) 0.2478(3) 0.27767(16) 0.0545(7) Uani 1 1 d . . .
C13 C 0.2565(4) 0.3661(3) 0.19330(18) 0.0605(8) Uani 1 1 d . . .
C14 C 0.1427(4) 0.2908(3) 0.17282(16) 0.0593(8) Uani 1 1 d . . .
C15 C 0.3275(5) 0.4638(4) 0.1602(2) 0.0813(11) Uani 1 1 d . . .
H15A H 0.3438 0.5253 0.1925 0.122 Uiso 1 1 calc R . .
H15B H 0.2573 0.4877 0.1204 0.122 Uiso 1 1 calc R . .
H15C H 0.4274 0.4416 0.1462 0.122 Uiso 1 1 calc R . .
C16 C 0.0390(5) 0.2786(4) 0.1060(2) 0.0881(12) Uani 1 1 d . . .
H16A H -0.0699 0.2764 0.1142 0.132 Uiso 1 1 calc R . .
H16B H 0.0649 0.2096 0.0838 0.132 Uiso 1 1 calc R . .
H16C H 0.0551 0.3418 0.0767 0.132 Uiso 1 1 calc R . .


_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 O3 1.928(2) . ?
Co1 O1 1.944(2) . ?
Co1 N1 1.982(3) . ?
Co1 N2 1.985(3) . ?
F1 C1 1.282(5) . ?
F2 C1 1.315(5) . ?
F3 C1 1.325(5) . ?
F4 C9 1.331(5) . ?
F5 C9 1.327(4) . ?
F6 C9 1.310(5) . ?
O1 C2 1.293(4) . ?
O2 C4 1.354(4) . ?
O2 C5 1.402(4) . ?
O3 C10 1.300(4) . ?
O4 C12 1.349(4) . ?
O4 C13 1.382(4) . ?
N1 C4 1.319(4) . ?
N1 C7 1.407(4) . ?
N2 C12 1.313(4) . ?
N2 C14 1.404(4) . ?
C1 C2 1.511(5) . ?
C2 C3 1.345(5) . ?
C3 C4 1.426(5) . ?
C3 H3 0.9300 . ?
C5 C7 1.323(5) . ?
C5 C6 1.495(5) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.496(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.509(5) . ?
C10 C11 1.349(5) . ?
C11 C12 1.419(4) . ?
C11 H11 0.9300 . ?
C13 C14 1.338(5) . ?
C13 C15 1.486(5) . ?
C14 C16 1.486(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
O3 Co1 O1 128.06(10) . . ?
O3 Co1 N1 115.75(11) . . ?
O1 Co1 N1 93.87(10) . . ?
O3 Co1 N2 94.25(10) . . ?
O1 Co1 N2 110.40(11) . . ?
N1 Co1 N2 116.04(10) . . ?
C2 O1 Co1 124.5(2) . . ?
C4 O2 C5 106.0(3) . . ?
C10 O3 Co1 124.2(2) . . ?
C12 O4 C13 105.9(2) . . ?
C4 N1 C7 106.2(3) . . ?
C4 N1 Co1 120.1(2) . . ?
C7 N1 Co1 132.6(2) . . ?
C12 N2 C14 105.5(3) . . ?
C12 N2 Co1 121.9(2) . . ?
C14 N2 Co1 132.6(2) . . ?
F1 C1 F2 108.4(5) . . ?
F1 C1 F3 105.3(4) . . ?
F2 C1 F3 102.0(4) . . ?
F1 C1 C2 115.5(4) . . ?
F2 C1 C2 112.3(4) . . ?
F3 C1 C2 112.4(4) . . ?
O1 C2 C3 127.9(3) . . ?
O1 C2 C1 112.8(3) . . ?
C3 C2 C1 119.3(3) . . ?
C2 C3 C4 122.8(3) . . ?
C2 C3 H3 118.6 . . ?
C4 C3 H3 118.6 . . ?
N1 C4 O2 111.2(3) . . ?
N1 C4 C3 128.5(3) . . ?
O2 C4 C3 120.3(3) . . ?
C7 C5 O2 107.8(3) . . ?
C7 C5 C6 135.0(4) . . ?
O2 C5 C6 117.2(3) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 N1 108.8(3) . . ?
C5 C7 C8 130.9(3) . . ?
N1 C7 C8 120.3(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
F6 C9 F5 107.6(4) . . ?
F6 C9 F4 106.9(4) . . ?
F5 C9 F4 104.5(3) . . ?
F6 C9 C10 114.2(3) . . ?
F5 C9 C10 111.7(3) . . ?
F4 C9 C10 111.4(3) . . ?
O3 C10 C11 129.0(3) . . ?
O3 C10 C9 112.8(3) . . ?
C11 C10 C9 118.2(3) . . ?
C10 C11 C12 122.6(3) . . ?
C10 C11 H11 118.7 . . ?
C12 C11 H11 118.7 . . ?
N2 C12 O4 112.2(3) . . ?
N2 C12 C11 127.8(3) . . ?
O4 C12 C11 120.0(3) . . ?
C14 C13 O4 107.9(3) . . ?
C14 C13 C15 134.7(3) . . ?
O4 C13 C15 117.3(3) . . ?
C13 C14 N2 108.5(3) . . ?
C13 C14 C16 130.8(3) . . ?
N2 C14 C16 120.7(3) . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
O3 Co1 O1 C2 -141.1(3) . . . . ?
N1 Co1 O1 C2 -13.8(3) . . . . ?
N2 Co1 O1 C2 105.8(3) . . . . ?
O1 Co1 O3 C10 -126.1(3) . . . . ?
N1 Co1 O3 C10 115.7(3) . . . . ?
N2 Co1 O3 C10 -6.0(3) . . . . ?
O3 Co1 N1 C4 151.9(2) . . . . ?
O1 Co1 N1 C4 16.0(3) . . . . ?
N2 Co1 N1 C4 -99.0(3) . . . . ?
O3 Co1 N1 C7 -41.9(3) . . . . ?
O1 Co1 N1 C7 -177.8(3) . . . . ?
N2 Co1 N1 C7 67.2(3) . . . . ?
O3 Co1 N2 C12 3.6(3) . . . . ?
O1 Co1 N2 C12 137.0(2) . . . . ?
N1 Co1 N2 C12 -117.8(2) . . . . ?
O3 Co1 N2 C14 -178.5(3) . . . . ?
O1 Co1 N2 C14 -45.1(3) . . . . ?
N1 Co1 N2 C14 60.1(3) . . . . ?
Co1 O1 C2 C3 6.8(5) . . . . ?
Co1 O1 C2 C1 -172.0(3) . . . . ?
F1 C1 C2 O1 -170.7(4) . . . . ?
F2 C1 C2 O1 64.4(5) . . . . ?
F3 C1 C2 O1 -49.8(5) . . . . ?
F1 C1 C2 C3 10.4(7) . . . . ?
F2 C1 C2 C3 -114.5(4) . . . . ?
F3 C1 C2 C3 131.2(4) . . . . ?
O1 C2 C3 C4 2.8(6) . . . . ?
C1 C2 C3 C4 -178.4(4) . . . . ?
C7 N1 C4 O2 -1.1(4) . . . . ?
Co1 N1 C4 O2 168.3(2) . . . . ?
C7 N1 C4 C3 177.8(3) . . . . ?
Co1 N1 C4 C3 -12.7(5) . . . . ?
C5 O2 C4 N1 1.0(4) . . . . ?
C5 O2 C4 C3 -178.0(3) . . . . ?
C2 C3 C4 N1 0.9(6) . . . . ?
C2 C3 C4 O2 179.8(3) . . . . ?
C4 O2 C5 C7 -0.4(4) . . . . ?
C4 O2 C5 C6 -179.2(3) . . . . ?
O2 C5 C7 N1 -0.3(4) . . . . ?
C6 C5 C7 N1 178.1(4) . . . . ?
O2 C5 C7 C8 178.4(4) . . . . ?
C6 C5 C7 C8 -3.2(8) . . . . ?
C4 N1 C7 C5 0.9(4) . . . . ?
Co1 N1 C7 C5 -166.7(3) . . . . ?
C4 N1 C7 C8 -177.9(3) . . . . ?
Co1 N1 C7 C8 14.5(5) . . . . ?
Co1 O3 C10 C11 5.8(5) . . . . ?
Co1 O3 C10 C9 -173.5(2) . . . . ?
F6 C9 C10 O3 -174.2(4) . . . . ?
F5 C9 C10 O3 -51.8(4) . . . . ?
F4 C9 C10 O3 64.7(4) . . . . ?
F6 C9 C10 C11 6.5(5) . . . . ?
F5 C9 C10 C11 128.8(4) . . . . ?
F4 C9 C10 C11 -114.7(4) . . . . ?
O3 C10 C11 C12 -1.2(6) . . . . ?
C9 C10 C11 C12 178.1(3) . . . . ?
C14 N2 C12 O4 -0.2(3) . . . . ?
Co1 N2 C12 O4 178.27(19) . . . . ?
C14 N2 C12 C11 -179.1(3) . . . . ?
Co1 N2 C12 C11 -0.7(5) . . . . ?
C13 O4 C12 N2 0.0(3) . . . . ?
C13 O4 C12 C11 179.0(3) . . . . ?
C10 C11 C12 N2 -1.6(5) . . . . ?
C10 C11 C12 O4 179.5(3) . . . . ?
C12 O4 C13 C14 0.1(4) . . . . ?
C12 O4 C13 C15 -178.5(3) . . . . ?
O4 C13 C14 N2 -0.2(4) . . . . ?
C15 C13 C14 N2 178.0(4) . . . . ?
O4 C13 C14 C16 -179.4(4) . . . . ?
C15 C13 C14 C16 -1.2(7) . . . . ?
C12 N2 C14 C13 0.2(4) . . . . ?
Co1 N2 C14 C13 -178.0(2) . . . . ?
C12 N2 C14 C16 179.5(3) . . . . ?
Co1 N2 C14 C16 1.4(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        26.74
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.050
