# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_MM-120
_database_code_depnum_ccdc_archive 'CCDC 2225026'
loop_
_audit_author_name
_audit_author_address
'Jean-Claude Daran'
;CNRS
France
;
_audit_update_record             
;
2023-04-20 deposited with the CCDC.	2023-04-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_sum            'C17 H19 Co O6'
_chemical_formula_weight         378.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co -2.3653 3.6143 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   10.8167(9)
_cell_length_b                   12.0499(11)
_cell_length_c                   13.5182(11)
_cell_angle_alpha                90
_cell_angle_beta                 103.533(9)
_cell_angle_gamma                90
_cell_volume                     1713.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    1065
_cell_measurement_theta_min      5.5520
_cell_measurement_theta_max      70.0670

_exptl_crystal_description       flattened
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    8.118
_shelx_estimated_absorpt_T_min   0.268
_shelx_estimated_absorpt_T_max   0.793
_exptl_absorpt_correction_T_min  0.42477
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      130(2)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1978
_diffrn_reflns_number            6407
_diffrn_reflns_av_unetI/netI     0.0885
_diffrn_reflns_av_R_equivalents  0.1133
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         5.583
_diffrn_reflns_theta_max         71.292
_diffrn_reflns_theta_full        67.680
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1655
_reflns_number_gt                975
_reflns_threshold_expression     'I > 2σ(I)'

_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       'CrysAlisPro (Rigaku Oxford-Diffraction, 2021)'
_computing_cell_refinement       'CrysAlisPro '
_computing_data_reduction        'CrysAlisPro '
_computing_structure_solution    'SHELXt (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
ORTEPIII (Burnett & Johnson, 1996); ORTEP-3 for Windows (Farrugia, 1997)
PLATON (Spek et al., 2009)
;
_computing_publication_material  'SHELXL-2018 (Sheldrick, 2018)'

_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     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0009(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1655
_refine_ls_number_parameters     114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2088
_refine_ls_R_factor_gt           0.1552
_refine_ls_wR_factor_ref         0.5302
_refine_ls_wR_factor_gt          0.4498
_refine_ls_goodness_of_fit_ref   1.827
_refine_ls_restrained_S_all      1.827
_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 0.500000 0.5111(2) 0.750000 0.0578(13) Uani 1 2 d S T P . .
O1 O 0.4270(10) 0.3771(8) 0.7918(7) 0.062(3) Uani 1 1 d . . . . .
O2 O 0.3678(11) 0.5036(8) 0.6321(9) 0.065(3) Uani 1 1 d . . . . .
O3 O 0.5982(10) 0.6213(8) 0.7037(8) 0.066(3) Uani 1 1 d . . . . .
C1 C 0.500000 0.3182(16) 0.750000 0.069(7) Uani 1 2 d S T P . .
C2 C 0.500000 0.1989(15) 0.750000 0.060(5) Uani 1 2 d S T P . .
C3 C 0.4087(15) 0.1408(12) 0.7853(11) 0.064(4) Uani 1 1 d . . . . .
H3 H 0.346137 0.180174 0.810159 0.076 Uiso 1 1 calc R U . . .
C4 C 0.4075(17) 0.0258(12) 0.7846(14) 0.074(5) Uani 1 1 d . . . . .
H4 H 0.343303 -0.013075 0.807855 0.089 Uiso 1 1 calc R U . . .
C5 C 0.500000 -0.0331(18) 0.750000 0.082(8) Uani 1 2 d S T P . .
H5 H 0.499999 -0.111920 0.749998 0.098 Uiso 1 2 calc R U P . .
C21 C 0.3608(16) 0.5695(11) 0.5568(11) 0.067(4) Uani 1 1 d . . . . .
C22 C 0.4450(18) 0.6498(12) 0.5480(14) 0.080(5) Uani 1 1 d . . . . .
H22 H 0.425800 0.695407 0.489078 0.096 Uiso 1 1 calc R U . . .
C23 C 0.5590(15) 0.6702(10) 0.6204(12) 0.064(4) Uani 1 1 d . . . . .
C24 C 0.2493(16) 0.5527(13) 0.4681(11) 0.069(4) Uani 1 1 d . . . . .
H24A H 0.273196 0.501758 0.419231 0.103 Uiso 1 1 calc R U . . .
H24B H 0.223966 0.624255 0.435011 0.103 Uiso 1 1 calc R U . . .
H24C H 0.178112 0.521334 0.492194 0.103 Uiso 1 1 calc R U . . .
C25 C 0.6520(18) 0.7571(13) 0.6006(15) 0.085(5) Uani 1 1 d . . . . .
H25A H 0.672410 0.808740 0.658182 0.128 Uiso 1 1 calc R U . . .
H25B H 0.613632 0.798122 0.538391 0.128 Uiso 1 1 calc R U . . .
H25C H 0.730055 0.720681 0.592541 0.128 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
Co1 O2 1.878(11) . ?
Co1 O2 1.878(11) 2_656 ?
Co1 O3 1.896(11) 2_656 ?
Co1 O3 1.896(11) . ?
Co1 O1 1.938(10) 2_656 ?
Co1 O1 1.938(10) . ?
Co1 C1 2.324(19) . ?
O1 C1 1.286(14) . ?
O2 C21 1.279(19) . ?
O3 C23 1.253(18) . ?
C1 C2 1.44(3) . ?
C2 C3 1.383(19) 2_656 ?
C2 C3 1.383(19) . ?
C3 C4 1.39(2) . ?
C4 C5 1.39(2) . ?
C21 C22 1.35(2) . ?
C21 C24 1.502(18) . ?
C22 C23 1.40(2) . ?
C23 C25 1.52(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
O2 Co1 O2 174.5(6) . 2_656 ?
O2 Co1 O3 86.6(4) . 2_656 ?
O2 Co1 O3 97.3(4) 2_656 2_656 ?
O2 Co1 O3 97.3(4) . . ?
O2 Co1 O3 86.6(4) 2_656 . ?
O3 Co1 O3 91.1(7) 2_656 . ?
O2 Co1 O1 89.6(4) . 2_656 ?
O2 Co1 O1 85.8(4) 2_656 2_656 ?
O3 Co1 O1 167.8(5) 2_656 2_656 ?
O3 Co1 O1 100.9(5) . 2_656 ?
O2 Co1 O1 85.8(4) . . ?
O2 Co1 O1 89.6(4) 2_656 . ?
O3 Co1 O1 100.9(5) 2_656 . ?
O3 Co1 O1 167.8(5) . . ?
O1 Co1 O1 67.2(7) 2_656 . ?
O2 Co1 C1 87.2(3) . . ?
O2 Co1 C1 87.2(3) 2_656 . ?
O3 Co1 C1 134.5(4) 2_656 . ?
O3 Co1 C1 134.5(4) . . ?
O1 Co1 C1 33.6(3) 2_656 . ?
O1 Co1 C1 33.6(3) . . ?
C1 O1 Co1 89.9(10) . . ?
C21 O2 Co1 122.5(11) . . ?
C23 O3 Co1 121.9(9) . . ?
O1 C1 O1 113.0(17) 2_656 . ?
O1 C1 C2 123.5(8) 2_656 . ?
O1 C1 C2 123.5(8) . . ?
O1 C1 Co1 56.5(8) 2_656 . ?
O1 C1 Co1 56.5(8) . . ?
C2 C1 Co1 180.0 . . ?
C3 C2 C3 119(2) 2_656 . ?
C3 C2 C1 120.4(10) 2_656 . ?
C3 C2 C1 120.4(10) . . ?
C2 C3 C4 120.7(18) . . ?
C3 C4 C5 120.3(19) . . ?
C4 C5 C4 119(2) 2_656 . ?
O2 C21 C22 126.7(15) . . ?
O2 C21 C24 116.0(15) . . ?
C22 C21 C24 117.2(15) . . ?
C21 C22 C23 124.3(16) . . ?
O3 C23 C22 126.9(15) . . ?
O3 C23 C25 112.6(13) . . ?
C22 C23 C25 120.5(15) . . ?

_refine_diff_density_max         1.366
_refine_diff_density_min         -2.292
_refine_diff_density_rms         0.184


# start Validation Reply Form
_vrf_PLAT084_MM-120              
;
PROBLEM: High wR2 Value (i.e. > 0.25) ................... 0.53 Report
RESPONSE: The crystal was poorly diffracting and the data above 40\% in 
theta are not reliable
;
_vrf_PLAT973_MM-120              
;
PROBLEM: Check Calcd Positive Resid. Density on Co1 2.42 eA-3
RESPONSE: Related to the poor quality of the data
;
_vrf_PLAT082_MM-120              
;
PROBLEM: High R1 Value .................................. 0.16 Report
RESPONSE: Related to the poor quality of the data...
;
_vrf_PLAT341_MM-120              
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.02067 Ang.
RESPONSE: The same reason as above
;
_vrf_PLAT972_MM-120              
;
PROBLEM: Check Calcd Resid. Dens. 0.85Ang From Co1 -2.58 eA-3
RESPONSE: The same as above. The geometry of the structure is certainly correct
but owing to the poor quality of the data, difficult to refine it correctly.
;
# end Validation Reply Form

