# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 2077372'
loop_
_audit_author_name
_audit_author_address
'Guilherme Pereira Guedes'
;Universidade Federal Fluminense
Brazil
;
_audit_update_record             
;
2021-04-13 deposited with the CCDC.	2021-08-16 downloaded from the CCDC.
;
# publcif _publ_body_element loop end
_audit_creation_date             2021-04-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2014/7
_publcif_funding_html            
;
;

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 O4'
_chemical_formula_sum            'C20 H14 O4'
_chemical_formula_weight         318.31
_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'
O O 0.0106 0.0060 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0604(4)
_cell_length_b                   10.6647(7)
_cell_length_c                   11.8334(7)
_cell_angle_alpha                75.773(3)
_cell_angle_beta                 73.159(2)
_cell_angle_gamma                74.351(3)
_cell_volume                     807.50(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9273
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.62
_cell_measurement_theta_min      2.46
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       neddle
_exptl_crystal_F_000             332
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 -1.00 -3.00 0.1030
-3.00 -2.00 0.00 0.0860
0.00 1.00 2.00 0.0830
2.00 3.00 3.00 0.0970
0.00 -3.00 1.00 0.0580
0.00 1.00 0.00 0.0670
0.00 -1.00 -3.00 0.1230
-3.00 -1.00 -3.00 0.1110

_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.254
_exptl_crystal_size_min          0.164
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23446
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.024
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_min         2.464
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8-Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2208
_reflns_number_total             2853
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker Instrument Service vV6.2.6'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.127(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2839
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0553
_refine_ls_restrained_S_all      1.112
_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)+(0.0565P)²+0.5678P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1416
_refine_ls_wR_factor_ref         0.1583
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C12(H12), C13(H13), C17(H17), C18(H18), C19(H19), C20(H20)
1.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     difmap
_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
O1 O 1.5985(2) 0.10212(18) 0.31046(16) 0.0524(5) Uani 1 1 d . . . . .
O2 O -0.4659(2) 0.83910(18) 1.16780(15) 0.0526(5) Uani 1 1 d . . . . .
O3 O -0.5912(3) 0.8538(2) 1.01170(19) 0.0725(7) Uani 1 1 d . . . . .
O4 O 1.7734(3) 0.1535(2) 0.4141(2) 0.0746(7) Uani 1 1 d . . . . .
C1 C 1.7849(4) 0.0339(3) 0.2409(2) 0.0548(7) Uani 1 1 d . . . . .
H1A H 1.8843 0.0875 0.2174 0.082 Uiso 1 1 calc R U . . .
H1B H 1.7604 0.0179 0.1705 0.082 Uiso 1 1 calc R U . . .
H1C H 1.8338 -0.0490 0.2885 0.082 Uiso 1 1 calc R U . . .
C2 C 1.6145(3) 0.1575(2) 0.3953(2) 0.0410(6) Uani 1 1 d . . . . .
C3 C 1.4144(3) 0.2233(2) 0.46240(19) 0.0375(5) Uani 1 1 d . . . . .
C4 C 1.2342(3) 0.2068(2) 0.4505(2) 0.0431(6) Uani 1 1 d . . . . .
H4 H 1.2358 0.1545 0.3977 0.052 Uiso 1 1 calc R U . . .
C5 C 1.0521(3) 0.2672(2) 0.5165(2) 0.0447(6) Uani 1 1 d . . . . .
H5 H 0.9315 0.2555 0.5079 0.054 Uiso 1 1 calc R U . . .
C6 C 1.0472(3) 0.3460(2) 0.59608(19) 0.0394(5) Uani 1 1 d . . . . .
C7 C 0.8563(4) 0.4069(2) 0.6642(2) 0.0425(6) Uani 1 1 d . . . . .
C8 C 0.6910(4) 0.4554(2) 0.7182(2) 0.0444(6) Uani 1 1 d . . . . .
C9 C 0.5025(4) 0.5126(2) 0.7779(2) 0.0447(6) Uani 1 1 d . . . . .
C10 C 0.3352(4) 0.5631(2) 0.8286(2) 0.0447(6) Uani 1 1 d . . . . .
C11 C 0.1376(3) 0.6255(2) 0.8874(2) 0.0407(6) Uani 1 1 d . . . . .
C12 C -0.0271(4) 0.6479(2) 0.8377(2) 0.0482(6) Uani 1 1 d . . . . .
H12 H -0.0093 0.6208 0.7657 0.058 Uiso 1 1 calc R U . . .
C13 C -0.2165(4) 0.7098(2) 0.8945(2) 0.0468(6) Uani 1 1 d . . . . .
H13 H -0.3258 0.7244 0.8606 0.056 Uiso 1 1 calc R U . . .
C14 C -0.2451(3) 0.7505(2) 1.0020(2) 0.0390(5) Uani 1 1 d . . . . .
C15 C -0.4517(4) 0.8191(2) 1.0585(2) 0.0441(6) Uani 1 1 d . . . . .
C16 C -0.6601(4) 0.9090(3) 1.2266(3) 0.0631(8) Uani 1 1 d . . . . .
H16A H -0.6903 0.9968 1.1814 0.095 Uiso 1 1 calc R U . . .
H16B H -0.6570 0.9140 1.3059 0.095 Uiso 1 1 calc R U . . .
H16C H -0.7625 0.8628 1.2318 0.095 Uiso 1 1 calc R U . . .
C17 C 0.1086(3) 0.6663(2) 0.9953(2) 0.0460(6) Uani 1 1 d . . . . .
H17 H 0.2175 0.6516 1.0296 0.055 Uiso 1 1 calc R U . . .
C18 C -0.0819(4) 0.7288(2) 1.0517(2) 0.0444(6) Uani 1 1 d . . . . .
H18 H -0.1002 0.7563 1.1236 0.053 Uiso 1 1 calc R U . . .
C19 C 1.4101(3) 0.3027(2) 0.5407(2) 0.0452(6) Uani 1 1 d . . . . .
H19 H 1.5309 0.3149 0.5487 0.054 Uiso 1 1 calc R U . . .
C20 C 1.2284(4) 0.3635(2) 0.6065(2) 0.0460(6) Uani 1 1 d . . . . .
H20 H 1.2273 0.4168 0.6584 0.055 Uiso 1 1 calc R U . . .


_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
O1 C1 1.445(3) . ?
O1 C2 1.328(3) . ?
O2 C15 1.333(3) . ?
O2 C16 1.439(3) . ?
O3 C15 1.197(3) . ?
O4 C2 1.193(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.486(3) . ?
C3 C4 1.381(3) . ?
C3 C19 1.390(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.377(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.396(3) . ?
C6 C7 1.429(3) . ?
C6 C20 1.386(3) . ?
C7 C8 1.201(3) . ?
C8 C9 1.368(3) . ?
C9 C10 1.204(3) . ?
C10 C11 1.428(3) . ?
C11 C12 1.390(3) . ?
C11 C17 1.392(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.377(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.387(3) . ?
C14 C15 1.486(3) . ?
C14 C18 1.382(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17 0.9300 . ?
C17 C18 1.383(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C19 C20 1.376(3) . ?
C20 H20 0.9300 . ?

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
C2 O1 C1 116.73(19) . . ?
C15 O2 C16 115.9(2) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 112.41(19) . . ?
O4 C2 O1 122.7(2) . . ?
O4 C2 C3 124.9(2) . . ?
C4 C3 C2 122.2(2) . . ?
C4 C3 C19 119.3(2) . . ?
C19 C3 C2 118.44(19) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.3(2) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.5(2) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C7 119.5(2) . . ?
C20 C6 C5 118.9(2) . . ?
C20 C6 C7 121.7(2) . . ?
C8 C7 C6 176.5(3) . . ?
C7 C8 C9 178.9(3) . . ?
C10 C9 C8 178.7(3) . . ?
C9 C10 C11 178.8(3) . . ?
C12 C11 C10 121.0(2) . . ?
C12 C11 C17 119.1(2) . . ?
C17 C11 C10 119.9(2) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.4(2) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C15 118.2(2) . . ?
C18 C14 C13 119.4(2) . . ?
C18 C14 C15 122.3(2) . . ?
O2 C15 C14 112.7(2) . . ?
O3 C15 O2 123.0(2) . . ?
O3 C15 C14 124.3(2) . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C11 C17 H17 119.9 . . ?
C18 C17 C11 120.1(2) . . ?
C18 C17 H17 119.9 . . ?
C14 C18 C17 120.5(2) . . ?
C14 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C3 C19 H19 119.8 . . ?
C20 C19 C3 120.5(2) . . ?
C20 C19 H19 119.8 . . ?
C6 C20 H20 119.8 . . ?
C19 C20 C6 120.5(2) . . ?
C19 C20 H20 119.8 . . ?

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
O1 C2 C3 C4 10.8(3) . . . . ?
O1 C2 C3 C19 -170.1(2) . . . . ?
O4 C2 C3 C4 -169.2(3) . . . . ?
O4 C2 C3 C19 10.0(4) . . . . ?
C1 O1 C2 O4 0.7(4) . . . . ?
C1 O1 C2 C3 -179.27(19) . . . . ?
C2 C3 C4 C5 178.5(2) . . . . ?
C2 C3 C19 C20 -178.7(2) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C3 C19 C20 C6 0.3(4) . . . . ?
C4 C3 C19 C20 0.5(4) . . . . ?
C4 C5 C6 C7 -179.6(2) . . . . ?
C4 C5 C6 C20 0.8(4) . . . . ?
C5 C6 C20 C19 -0.9(4) . . . . ?
C7 C6 C20 C19 179.4(2) . . . . ?
C10 C11 C12 C13 -179.1(2) . . . . ?
C10 C11 C17 C18 179.0(2) . . . . ?
C11 C12 C13 C14 -0.1(4) . . . . ?
C11 C17 C18 C14 0.4(4) . . . . ?
C12 C11 C17 C18 -0.3(4) . . . . ?
C12 C13 C14 C15 178.9(2) . . . . ?
C12 C13 C14 C18 0.2(4) . . . . ?
C13 C14 C15 O2 172.4(2) . . . . ?
C13 C14 C15 O3 -8.0(4) . . . . ?
C13 C14 C18 C17 -0.3(4) . . . . ?
C15 C14 C18 C17 -179.0(2) . . . . ?
C16 O2 C15 O3 -1.6(4) . . . . ?
C16 O2 C15 C14 178.0(2) . . . . ?
C17 C11 C12 C13 0.1(4) . . . . ?
C18 C14 C15 O2 -8.9(3) . . . . ?
C18 C14 C15 O3 170.7(3) . . . . ?
C19 C3 C4 C5 -0.7(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_CoCP
_database_code_depnum_ccdc_archive 'CCDC 2077373'
loop_
_audit_author_name
_audit_author_address
'Guilherme Pereira Guedes'
;Universidade Federal Fluminense
Brazil
;

_audit_update_record             
;
2021-04-14 deposited with the CCDC.	2021-08-16 downloaded from the CCDC.
;
# publcif _publ_body_element loop end
_audit_creation_date             2021-04-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H20 Co N2 O5'
_chemical_formula_sum            'C28 H20 Co N2 O5'
_chemical_formula_weight         523.39
_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'
Co Co 0.3494 0.9721 '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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.6551(3)
_cell_length_b                   17.7754(5)
_cell_length_c                   16.1528(5)
_cell_angle_alpha                90
_cell_angle_beta                 103.4240(10)
_cell_angle_gamma                90
_cell_volume                     2417.18(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9988
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.68
_cell_measurement_theta_min      2.29
_shelx_estimated_absorpt_T_max   0.888
_shelx_estimated_absorpt_T_min   0.799
_exptl_absorpt_coefficient_mu    0.752
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0938 before and 0.0489 after correction.
The Ratio of minimum to maximum transmission is 0.9229.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            pink
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1076
_exptl_crystal_size_max          0.313
_exptl_crystal_size_mid          0.167
_exptl_crystal_size_min          0.162
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            28501
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.023
_diffrn_reflns_theta_max         25.023
_diffrn_reflns_theta_min         2.292
_diffrn_ambient_temperature      298(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 D8-Venture'
_diffrn_measurement_method       'φ and ω 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                3774
_reflns_number_total             4277
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'Bruker Instrument Service vV6.2.6'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0061(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4277
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0281
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0246P)²+1.6586P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0651
_refine_ls_wR_factor_ref         0.0688
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 Co1, O3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(O3) = Uanis(O4)
4.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C24(H24), C13(H13), C3(H3), C16(H16), C23(H23), C17(H17), C21(H21),
 C28(H28), C6(H6), C19(H19), C14(H14), C7(H7), C20(H20), C22(H22), C25(H25),
 C26(H26), C27(H27)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_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
Co1 Co 0.54190(3) 0.63838(2) 0.04257(2) 0.02590(10) Uani 1 1 d . U . . .
OW O 0.37848(17) 0.57229(8) -0.04226(9) 0.0349(3) Uani 1 1 d . . . . .
O3 O 0.65321(16) 0.66969(8) -0.05590(8) 0.0381(2) Uani 1 1 d . U . . .
O4 O 0.74575(16) 0.56494(8) 0.00778(8) 0.0381(2) Uani 1 1 d . . . . .
O1 O 0.43467(17) 0.60360(8) 0.13464(8) 0.0427(3) Uani 1 1 d . . . . .
O2 O 0.5408(2) 0.49101(10) 0.17316(9) 0.0573(4) Uani 1 1 d . . . . .
N1 N 0.37804(18) 0.72955(9) 0.01177(10) 0.0329(4) Uani 1 1 d . . . . .
N2 N 0.71133(19) 0.70131(9) 0.13637(10) 0.0350(4) Uani 1 1 d . . . . .
C15 C 0.8310(2) 0.59963(10) -0.11800(11) 0.0278(4) Uani 1 1 d . . . . .
C4 C 0.2418(3) 0.61081(12) 0.34863(13) 0.0405(5) Uani 1 1 d . . . . .
H4 H 0.1783 0.6508 0.3577 0.049 Uiso 1 1 calc R U . . .
C10 C 1.1183(2) 0.55985(12) -0.37861(12) 0.0374(5) Uani 1 1 d . . . . .
C24 C 0.6749(3) 0.72444(13) 0.20780(13) 0.0452(5) Uani 1 1 d . . . . .
H24 H 0.5808 0.7072 0.2195 0.054 Uiso 1 1 calc R U . . .
C13 C 0.8946(2) 0.63984(12) -0.24825(12) 0.0396(5) Uani 1 1 d . . . . .
H13 H 0.8832 0.6744 -0.2924 0.048 Uiso 1 1 calc R U . . .
C3 C 0.2996(2) 0.60868(12) 0.27568(12) 0.0378(5) Uani 1 1 d . . . . .
H3 H 0.2742 0.6472 0.2359 0.045 Uiso 1 1 calc R U . . .
C5 C 0.2784(2) 0.55331(11) 0.40833(11) 0.0310(4) Uani 1 1 d . . . . .
C11 C 1.0627(2) 0.56445(12) -0.31752(13) 0.0406(5) Uani 1 1 d . . . . .
C2 C 0.3948(2) 0.54986(10) 0.26122(11) 0.0285(4) Uani 1 1 d . . . . .
C12 C 0.9883(2) 0.57592(12) -0.24808(12) 0.0351(4) Uani 1 1 d . . . . .
C16 C 0.9246(2) 0.53680(12) -0.11767(12) 0.0358(4) Uani 1 1 d . . . . .
H16 H 0.9340 0.5018 -0.0740 0.043 Uiso 1 1 calc R U . . .
C23 C 0.4262(3) 0.79448(11) -0.01380(15) 0.0454(5) Uani 1 1 d . . . . .
H23 H 0.5346 0.8018 -0.0081 0.055 Uiso 1 1 calc R U . . .
C17 C 1.0048(2) 0.52496(12) -0.18141(12) 0.0395(5) Uani 1 1 d . . . . .
H17 H 1.0696 0.4830 -0.1796 0.047 Uiso 1 1 calc R U . . .
C21 C 0.1650(3) 0.84163(14) -0.05627(16) 0.0554(6) Uani 1 1 d . . . . .
H21 H 0.0934 0.8795 -0.0789 0.066 Uiso 1 1 calc R U . . .
C28 C 0.8478(3) 0.72620(17) 0.12305(16) 0.0685(8) Uani 1 1 d . . . . .
H28 H 0.8781 0.7104 0.0743 0.082 Uiso 1 1 calc R U . . .
C6 C 0.3724(2) 0.49400(11) 0.39324(12) 0.0349(4) Uani 1 1 d . . . . .
H6 H 0.3968 0.4550 0.4324 0.042 Uiso 1 1 calc R U . . .
C9 C 0.1774(2) 0.55652(11) 0.54980(12) 0.0349(4) Uani 1 1 d . . . . .
C19 C 0.2222(3) 0.72029(13) 0.00353(15) 0.0478(5) Uani 1 1 d . . . . .
H19 H 0.1863 0.6752 0.0214 0.057 Uiso 1 1 calc R U . . .
C8 C 0.2228(2) 0.55529(11) 0.48519(12) 0.0355(4) Uani 1 1 d . . . . .
C14 C 0.8190(2) 0.65186(11) -0.18318(12) 0.0355(4) Uani 1 1 d . . . . .
H14 H 0.7593 0.6953 -0.1829 0.043 Uiso 1 1 calc R U . . .
C7 C 0.4301(2) 0.49256(11) 0.32040(12) 0.0337(4) Uani 1 1 d . . . . .
H7 H 0.4934 0.4526 0.3111 0.040 Uiso 1 1 calc R U . . .
C18 C 0.7391(2) 0.61149(11) -0.05117(11) 0.0303(4) Uani 1 1 d . . . . .
C1 C 0.4628(2) 0.54717(11) 0.18331(11) 0.0335(4) Uani 1 1 d . . . . .
C20 C 0.1124(3) 0.77465(15) -0.03021(16) 0.0563(6) Uani 1 1 d . . . . .
H20 H 0.0046 0.7662 -0.0353 0.068 Uiso 1 1 calc R U . . .
C22 C 0.3246(3) 0.85156(12) -0.04826(18) 0.0587(7) Uani 1 1 d . . . . .
H22 H 0.3634 0.8961 -0.0658 0.070 Uiso 1 1 calc R U . . .
C25 C 0.7681(3) 0.77228(13) 0.26545(14) 0.0497(6) Uani 1 1 d . . . . .
H25 H 0.7370 0.7868 0.3145 0.060 Uiso 1 1 calc R U . . .
C26 C 0.9061(3) 0.79785(15) 0.24957(15) 0.0578(6) Uani 1 1 d . . . . .
H26 H 0.9711 0.8307 0.2870 0.069 Uiso 1 1 calc R U . . .
C27 C 0.9469(3) 0.7741(2) 0.17746(19) 0.0840(10) Uani 1 1 d . . . . .
H27 H 1.0412 0.7903 0.1651 0.101 Uiso 1 1 calc R U . . .
HWA H 0.337(3) 0.5394(15) -0.0209(17) 0.062(9) Uiso 1 1 d . . . . .
HWB H 0.404(3) 0.5544(15) -0.0824(18) 0.062(8) Uiso 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 OW 2.0877(14) . ?
Co1 O3 2.1165(12) . ?
Co1 O4 2.3650(13) . ?
Co1 O1 2.0239(12) . ?
Co1 N1 2.1348(15) . ?
Co1 N2 2.1600(16) . ?
OW HWA 0.81(3) . ?
OW HWB 0.80(3) . ?
O3 C18 1.266(2) . ?
O4 C18 1.253(2) . ?
O1 C1 1.263(2) . ?
O2 C1 1.237(2) . ?
N1 C23 1.325(3) . ?
N1 C19 1.334(3) . ?
N2 C24 1.330(2) . ?
N2 C28 1.325(3) . ?
C15 C16 1.379(3) . ?
C15 C14 1.389(3) . ?
C15 C18 1.497(2) . ?
C4 H4 0.9300 . ?
C4 C3 1.383(3) . ?
C4 C5 1.390(3) . ?
C10 C11 1.197(3) . ?
C10 C9 1.370(3) 1_654 ?
C24 H24 0.9300 . ?
C24 C25 1.375(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.395(3) . ?
C13 C14 1.378(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.384(3) . ?
C5 C6 1.388(3) . ?
C5 C8 1.432(2) . ?
C11 C12 1.432(2) . ?
C2 C7 1.382(3) . ?
C2 C1 1.509(2) . ?
C12 C17 1.389(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.385(3) . ?
C23 H23 0.9300 . ?
C23 C22 1.374(3) . ?
C17 H17 0.9300 . ?
C21 H21 0.9300 . ?
C21 C20 1.375(4) . ?
C21 C22 1.369(4) . ?
C28 H28 0.9300 . ?
C28 C27 1.373(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.381(2) . ?
C9 C10 1.370(3) 1_456 ?
C9 C8 1.197(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.376(3) . ?
C14 H14 0.9300 . ?
C7 H7 0.9300 . ?
C20 H20 0.9300 . ?
C22 H22 0.9300 . ?
C25 H25 0.9300 . ?
C25 C26 1.357(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.360(4) . ?
C27 H27 0.9300 . ?

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
OW Co1 O3 90.68(6) . . ?
OW Co1 O4 87.85(5) . . ?
OW Co1 N1 87.83(6) . . ?
OW Co1 N2 176.36(6) . . ?
O3 Co1 O4 58.11(5) . . ?
O3 Co1 N1 91.09(6) . . ?
O3 Co1 N2 92.16(6) . . ?
O1 Co1 OW 87.36(6) . . ?
O1 Co1 O3 177.39(6) . . ?
O1 Co1 O4 120.04(5) . . ?
O1 Co1 N1 90.57(6) . . ?
O1 Co1 N2 89.73(6) . . ?
N1 Co1 O4 148.82(5) . . ?
N1 Co1 N2 94.39(6) . . ?
N2 Co1 O4 91.72(5) . . ?
Co1 OW HWA 115.4(19) . . ?
Co1 OW HWB 118.8(19) . . ?
HWA OW HWB 107(3) . . ?
C18 O3 Co1 95.93(11) . . ?
C18 O4 Co1 84.90(11) . . ?
C1 O1 Co1 130.18(13) . . ?
C23 N1 Co1 119.57(13) . . ?
C23 N1 C19 117.41(18) . . ?
C19 N1 Co1 122.07(14) . . ?
C24 N2 Co1 120.65(14) . . ?
C28 N2 Co1 123.01(14) . . ?
C28 N2 C24 115.93(18) . . ?
C16 C15 C14 118.99(16) . . ?
C16 C15 C18 121.41(17) . . ?
C14 C15 C18 119.58(17) . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.09(18) . . ?
C5 C4 H4 120.0 . . ?
C11 C10 C9 177.7(2) . 1_654 ?
N2 C24 H24 118.0 . . ?
N2 C24 C25 124.0(2) . . ?
C25 C24 H24 118.0 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C14 C13 C12 120.24(18) . . ?
C4 C3 H3 119.6 . . ?
C4 C3 C2 120.77(18) . . ?
C2 C3 H3 119.6 . . ?
C4 C5 C8 120.99(17) . . ?
C6 C5 C4 119.02(16) . . ?
C6 C5 C8 119.98(17) . . ?
C10 C11 C12 174.7(2) . . ?
C3 C2 C1 121.83(17) . . ?
C7 C2 C3 119.00(16) . . ?
C7 C2 C1 119.16(17) . . ?
C13 C12 C11 118.76(18) . . ?
C17 C12 C13 119.19(17) . . ?
C17 C12 C11 122.04(19) . . ?
C15 C16 H16 119.5 . . ?
C15 C16 C17 121.04(18) . . ?
C17 C16 H16 119.5 . . ?
N1 C23 H23 118.3 . . ?
N1 C23 C22 123.4(2) . . ?
C22 C23 H23 118.3 . . ?
C12 C17 H17 120.1 . . ?
C16 C17 C12 119.88(19) . . ?
C16 C17 H17 120.1 . . ?
C20 C21 H21 120.6 . . ?
C22 C21 H21 120.6 . . ?
C22 C21 C20 118.8(2) . . ?
N2 C28 H28 118.3 . . ?
N2 C28 C27 123.5(2) . . ?
C27 C28 H28 118.3 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.44(17) . . ?
C7 C6 H6 119.8 . . ?
C8 C9 C10 176.9(2) . 1_456 ?
N1 C19 H19 118.6 . . ?
N1 C19 C20 122.8(2) . . ?
C20 C19 H19 118.6 . . ?
C9 C8 C5 179.4(2) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 C15 120.61(19) . . ?
C13 C14 H14 119.7 . . ?
C2 C7 H7 119.7 . . ?
C6 C7 C2 120.67(17) . . ?
C6 C7 H7 119.7 . . ?
O3 C18 C15 118.33(16) . . ?
O4 C18 O3 120.53(16) . . ?
O4 C18 C15 121.14(17) . . ?
O1 C1 C2 115.99(17) . . ?
O2 C1 O1 126.20(17) . . ?
O2 C1 C2 117.81(17) . . ?
C21 C20 C19 118.8(2) . . ?
C21 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
C23 C22 H22 120.6 . . ?
C21 C22 C23 118.7(2) . . ?
C21 C22 H22 120.6 . . ?
C24 C25 H25 120.6 . . ?
C26 C25 C24 118.9(2) . . ?
C26 C25 H25 120.6 . . ?
C25 C26 H26 120.9 . . ?
C25 C26 C27 118.2(2) . . ?
C27 C26 H26 120.9 . . ?
C28 C27 H27 120.2 . . ?
C26 C27 C28 119.5(2) . . ?
C26 C27 H27 120.2 . . ?

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
Co1 O3 C18 O4 -7.68(19) . . . . ?
Co1 O3 C18 C15 171.83(13) . . . . ?
Co1 O4 C18 O3 6.86(17) . . . . ?
Co1 O4 C18 C15 -172.63(16) . . . . ?
Co1 O1 C1 O2 -17.1(3) . . . . ?
Co1 O1 C1 C2 162.45(12) . . . . ?
Co1 N1 C23 C22 168.74(19) . . . . ?
Co1 N1 C19 C20 -168.55(18) . . . . ?
Co1 N2 C24 C25 -171.73(18) . . . . ?
Co1 N2 C28 C27 171.4(3) . . . . ?
N1 C23 C22 C21 0.5(4) . . . . ?
N1 C19 C20 C21 -0.3(4) . . . . ?
N2 C24 C25 C26 -0.1(4) . . . . ?
N2 C28 C27 C26 0.4(5) . . . . ?
C15 C16 C17 C12 -1.6(3) . . . . ?
C4 C3 C2 C7 0.7(3) . . . . ?
C4 C3 C2 C1 -178.42(18) . . . . ?
C4 C5 C6 C7 0.7(3) . . . . ?
C24 N2 C28 C27 -1.3(4) . . . . ?
C24 C25 C26 C27 -0.7(4) . . . . ?
C13 C12 C17 C16 2.1(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C3 C4 C5 C8 178.55(19) . . . . ?
C3 C2 C7 C6 -0.4(3) . . . . ?
C3 C2 C1 O1 3.7(3) . . . . ?
C3 C2 C1 O2 -176.80(19) . . . . ?
C5 C4 C3 C2 -0.3(3) . . . . ?
C5 C6 C7 C2 -0.3(3) . . . . ?
C11 C12 C17 C16 -177.03(19) . . . . ?
C12 C13 C14 C15 -1.9(3) . . . . ?
C16 C15 C14 C13 2.4(3) . . . . ?
C16 C15 C18 O3 -178.77(17) . . . . ?
C16 C15 C18 O4 0.7(3) . . . . ?
C23 N1 C19 C20 0.3(3) . . . . ?
C28 N2 C24 C25 1.1(3) . . . . ?
C19 N1 C23 C22 -0.4(3) . . . . ?
C8 C5 C6 C7 -178.29(18) . . . . ?
C14 C15 C16 C17 -0.6(3) . . . . ?
C14 C15 C18 O3 -0.5(3) . . . . ?
C14 C15 C18 O4 179.04(17) . . . . ?
C14 C13 C12 C11 178.80(19) . . . . ?
C14 C13 C12 C17 -0.3(3) . . . . ?
C7 C2 C1 O1 -175.46(17) . . . . ?
C7 C2 C1 O2 4.1(3) . . . . ?
C18 C15 C16 C17 177.72(18) . . . . ?
C18 C15 C14 C13 -175.99(18) . . . . ?
C1 C2 C7 C6 178.72(17) . . . . ?
C20 C21 C22 C23 -0.6(4) . . . . ?
C22 C21 C20 C19 0.5(4) . . . . ?
C25 C26 C27 C28 0.6(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'



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