# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_100K
_database_code_depnum_ccdc_archive 'CCDC 2211956'
_audit_update_record             
;
2022-10-08 deposited with the CCDC.	2022-11-10 downloaded from the CCDC.
;
_audit_creation_date             2022-10-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Co H12 O6, C10 H4 O8'
_chemical_formula_sum            'C10 H16 Co O14'
_chemical_formula_weight         419.16
_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'
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           10
_space_group_name_H-M_alt        'P 1 2/m 1'
_space_group_name_Hall           '-P 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'-x, -y, -z'
'x, -y, z'

_cell_length_a                   6.3747(5)
_cell_length_b                   9.9302(8)
_cell_length_c                   6.4394(6)
_cell_angle_alpha                90
_cell_angle_beta                 114.467(2)
_cell_angle_gamma                90
_cell_volume                     371.02(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    5044
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      33.14
_cell_measurement_theta_min      3.48
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.237
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_correction_T_min  0.6024
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1231 before and 0.0674 after correction.
The Ratio of minimum to maximum transmission is 0.8067.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.876
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             215
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.943
_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       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6878
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.038
_diffrn_reflns_theta_min         2.051
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                883
_reflns_number_total             912
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.728
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     71
_refine_ls_number_reflns         912
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0323
_refine_ls_restrained_S_all      1.128
_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)+(0.0499P)²+0.2336P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0894
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 Co1-H2A \\sim Co1-H2B
 with sigma of 0.02
3. Others
 Fixed Sof: H1A(0.5) H1B(0.5) H2A(0.5) H2B(0.5) H3A(0.5) H3B(0.5)
4.a Free rotating group:
 O2(H2A,H2B)
4.b Rotating group:
 O1(H1A,H1B), O3(H3A,H3B)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.000000 0.500000 0.500000 0.02024(19) Uani 1 4 d DS T P . .
O1 O -0.1246(5) 0.500000 0.7422(5) 0.0495(7) Uani 1 2 d S T P . .
H1A H -0.166918 0.582146 0.761277 0.074 Uiso 0.5 1 d R U P . .
H1B H -0.254089 0.453330 0.695372 0.074 Uiso 0.5 1 d R U P . .
O2 O 0.000000 0.2868(2) 0.500000 0.0388(5) Uani 1 2 d GS T P . .
H2A H 0.109757 0.238463 0.598956 0.058 Uiso 0.5 1 d DG U P . .
H2B H -0.123262 0.237831 0.463923 0.058 Uiso 0.5 1 d DG U P . .
O3 O 0.3248(4) 0.500000 0.7532(5) 0.0421(6) Uani 1 2 d S T P . .
H3A H 0.386351 0.421090 0.765411 0.063 Uiso 0.5 1 d R U P . .
H3B H 0.411921 0.551969 0.717660 0.063 Uiso 0.5 1 d R U P . .
O4 O 0.3856(2) 0.88009(15) 0.6995(3) 0.0369(4) Uani 1 1 d . . . . .
O5 O 0.6237(3) 0.71135(15) 0.8061(3) 0.0405(4) Uani 1 1 d . . . . .
C1 C 0.5890(3) 0.83296(19) 0.7928(3) 0.0244(4) Uani 1 1 d . . . . .
C2 C 0.7911(3) 0.92889(17) 0.8934(3) 0.0197(4) Uani 1 1 d . . . . .
C3 C 1.000000 0.8635(3) 1.000000 0.0212(5) Uani 1 2 d S T P . .
H3 H 1.000002 0.767869 1.000000 0.025 Uiso 1 2 calc R U P . .
H4 H 0.388(9) 1.000000 0.709(8) 0.060(13) Uiso 1 2 d S . 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
Co1 O1 2.023(2) . ?
Co1 O1 2.023(2) 3_566 ?
Co1 O2 2.117(2) . ?
Co1 O2 2.117(2) 3_566 ?
Co1 O3 2.037(2) . ?
Co1 O3 2.037(2) 3_566 ?
O1 H1A 0.883(17) 4_565 ?
O1 H1A 0.8835 . ?
O1 H1B 0.88(4) 4_565 ?
O1 H1B 0.8835 . ?
O2 H2A 0.87(3) 2_556 ?
O2 H2A 0.8700 . ?
O2 H2B 0.8700 . ?
O2 H2B 0.87(3) 2_556 ?
O3 H3A 0.87(2) 4_565 ?
O3 H3A 0.8652 . ?
O3 H3B 0.8558 . ?
O3 H3B 0.86(5) 4_565 ?
O4 C1 1.271(2) . ?
O4 H4 1.192(3) . ?
O5 C1 1.224(3) . ?
C1 C2 1.515(2) . ?
C2 C2 1.412(3) 4_575 ?
C2 C3 1.381(2) . ?
C3 H3 0.9500 . ?

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 180.0 . 3_566 ?
O1 Co1 O2 90.0 3_566 3_566 ?
O1 Co1 O2 90.0 3_566 . ?
O1 Co1 O2 90.0 . 3_566 ?
O1 Co1 O2 90.000(1) . . ?
O1 Co1 O3 88.65(13) . . ?
O1 Co1 O3 91.35(13) 3_566 . ?
O1 Co1 O3 88.65(13) 3_566 3_566 ?
O1 Co1 O3 91.35(13) . 3_566 ?
O2 Co1 O2 180.0 . 3_566 ?
O3 Co1 O2 90.0 3_566 . ?
O3 Co1 O2 90.0 . . ?
O3 Co1 O2 90.0 3_566 3_566 ?
O3 Co1 O2 90.0 . 3_566 ?
O3 Co1 O3 180.0 . 3_566 ?
Co1 O1 H1A 110.3 . . ?
Co1 O1 H1A 110.3(4) . 4_565 ?
Co1 O1 H1B 110.3(11) . 4_565 ?
Co1 O1 H1B 110.3 . . ?
H1A O1 H1A 134.8 . 4_565 ?
H1A O1 H1B 103.7 4_565 4_565 ?
H1A O1 H1B 42.9 . 4_565 ?
H1A O1 H1B 103.7 . . ?
H1B O1 H1A 42.9 . 4_565 ?
H1B O1 H1B 63.3 . 4_565 ?
Co1 O2 H2A 123.5(7) . 2_556 ?
Co1 O2 H2A 123.5 . . ?
Co1 O2 H2B 124.0(7) . 2_556 ?
Co1 O2 H2B 124.0 . . ?
H2A O2 H2A 113.0 . 2_556 ?
H2A O2 H2B 29.8 . 2_556 ?
H2A O2 H2B 104.5 2_556 2_556 ?
H2A O2 H2B 104.5 . . ?
H2B O2 H2A 29.8 . 2_556 ?
H2B O2 H2B 112.0 . 2_556 ?
Co1 O3 H3A 110.2 . . ?
Co1 O3 H3A 110.2(6) . 4_565 ?
Co1 O3 H3B 110.1(12) . 4_565 ?
Co1 O3 H3B 110.1 . . ?
H3A O3 H3A 129.8 . 4_565 ?
H3A O3 H3B 104.5 . . ?
H3A O3 H3B 32.7 . 4_565 ?
H3A O3 H3B 104.5 4_565 4_565 ?
H3B O3 H3A 32.7 . 4_565 ?
H3B O3 H3B 74.2 . 4_565 ?
C1 O4 H4 111(3) . . ?
O4 C1 C2 119.40(16) . . ?
O5 C1 O4 121.04(17) . . ?
O5 C1 C2 119.55(17) . . ?
C2 C2 C1 128.95(10) 4_575 . ?
C3 C2 C1 113.02(16) . . ?
C3 C2 C2 118.02(11) . 4_575 ?
C2 C3 C2 124.0(2) . 2_757 ?
C2 C3 H3 118.0 . . ?
C2 C3 H3 118.0 2_757 . ?

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
O4 C1 C2 C2 -2.6(2) . . . 4_575 ?
O4 C1 C2 C3 176.60(16) . . . . ?
O5 C1 C2 C2 178.62(14) . . . 4_575 ?
O5 C1 C2 C3 -2.2(3) . . . . ?
C1 C2 C3 C2 -179.31(16) . . . 2_757 ?
C2 C2 C3 C2 0.001(2) 4_575 . . 2_757 ?

_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_300K
_database_code_depnum_ccdc_archive 'CCDC 2211957'
_audit_update_record             
;
2022-10-08 deposited with the CCDC.	2022-11-10 downloaded from the CCDC.
;
_audit_creation_date             2022-09-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Co H12 O6, C10 H4 O8'
_chemical_formula_sum            'C10 H16 Co O14'
_chemical_formula_weight         419.16
_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'
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           10
_space_group_name_H-M_alt        'P 1 2/m 1'
_space_group_name_Hall           '-P 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'-x, -y, -z'
'x, -y, z'

_cell_length_a                   6.4912(5)
_cell_length_b                   9.9169(8)
_cell_length_c                   6.5380(6)
_cell_angle_alpha                90
_cell_angle_beta                 115.401(2)
_cell_angle_gamma                90
_cell_volume                     380.18(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4836
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      3.45
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.207
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6447
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1198 before and 0.0476 after correction.
The Ratio of minimum to maximum transmission is 0.8647.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.831
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             215
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.973
_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       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6878
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.515
_diffrn_reflns_theta_min         2.054
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                883
_reflns_number_total             912
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.738
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     71
_refine_ls_number_reflns         912
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0319
_refine_ls_restrained_S_all      1.126
_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)+(0.0495P)²+0.2256P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.0881
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 Co1-H2A \\sim Co1-H2B
 with sigma of 0.02
3. Others
 Fixed Sof: H1A(0.5) H1B(0.5) H2A(0.5) H2B(0.5) H3A(0.5) H3B(0.5)
4.a Free rotating group:
 O2(H2A,H2B)
4.b Rotating group:
 O1(H1A,H1B), O3(H3A,H3B)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.000000 0.500000 0.500000 0.02075(19) Uani 1 4 d DS T P . .
O1 O -0.1245(5) 0.500000 0.7422(5) 0.0503(7) Uani 1 2 d S T P . .
H1A H -0.165571 0.580401 0.759748 0.075 Uiso 0.5 1 d R U P . .
H1B H -0.249591 0.454167 0.695253 0.075 Uiso 0.5 1 d R U P . .
O2 O 0.000000 0.2868(2) 0.500000 0.0400(6) Uani 1 2 d GS T P . .
H2A H 0.108119 0.239692 0.594853 0.060 Uiso 0.5 1 d DG U P . .
H2B H -0.118669 0.239189 0.468210 0.060 Uiso 0.5 1 d DG U P . .
O3 O 0.3248(3) 0.500000 0.7531(4) 0.0435(6) Uani 1 2 d S T P . .
H3A H 0.385113 0.421320 0.765054 0.065 Uiso 0.5 1 d R U P . .
H3B H 0.410773 0.551490 0.716804 0.065 Uiso 0.5 1 d R U P . .
O4 O 0.3856(2) 0.88008(15) 0.6995(3) 0.0379(4) Uani 1 1 d . . . . .
O5 O 0.6237(3) 0.71134(14) 0.8061(3) 0.0416(4) Uani 1 1 d . . . . .
C1 C 0.5890(3) 0.83297(19) 0.7928(3) 0.0248(4) Uani 1 1 d . . . . .
C2 C 0.7911(3) 0.92890(17) 0.8934(3) 0.0201(4) Uani 1 1 d . . . . .
C3 C 1.000000 0.8636(2) 1.000000 0.0217(5) Uani 1 2 d S T P . .
H3 H 1.000001 0.769779 0.999998 0.026 Uiso 1 2 calc R U P . .
H4 H 0.388(9) 1.000000 0.708(8) 0.064(13) Uiso 1 2 d S . 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
Co1 O1 2.064(2) . ?
Co1 O1 2.064(2) 3_566 ?
Co1 O2 2.114(2) 3_566 ?
Co1 O2 2.114(2) . ?
Co1 O3 2.047(2) . ?
Co1 O3 2.047(2) 3_566 ?
O1 H1A 0.8637 . ?
O1 H1A 0.864(17) 4_565 ?
O1 H1B 0.86(4) 4_565 ?
O1 H1B 0.8638 . ?
O2 H2A 0.8499 . ?
O2 H2A 0.85(3) 2_556 ?
O2 H2B 0.85(3) 2_556 ?
O2 H2B 0.8500 . ?
O3 H3A 0.86(2) 4_565 ?
O3 H3A 0.8614 . ?
O3 H3B 0.86(5) 4_565 ?
O3 H3B 0.8616 . ?
O4 C1 1.282(2) . ?
O4 H4 1.190(3) . ?
O5 C1 1.223(2) . ?
C1 C2 1.523(2) . ?
C2 C2 1.410(3) 4_575 ?
C2 C3 1.390(2) . ?
C3 H3 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
O1 Co1 O1 180.00(18) . 3_566 ?
O1 Co1 O2 90.0 3_566 3_566 ?
O1 Co1 O2 90.000(1) . . ?
O1 Co1 O2 90.0 3_566 . ?
O1 Co1 O2 90.0 . 3_566 ?
O2 Co1 O2 180.0 3_566 . ?
O3 Co1 O1 90.79(12) . 3_566 ?
O3 Co1 O1 89.21(12) 3_566 3_566 ?
O3 Co1 O1 89.21(12) . . ?
O3 Co1 O1 90.79(12) 3_566 . ?
O3 Co1 O2 90.0 . 3_566 ?
O3 Co1 O2 90.0 3_566 . ?
O3 Co1 O2 90.0 . . ?
O3 Co1 O2 90.0 3_566 3_566 ?
O3 Co1 O3 180.0 . 3_566 ?
Co1 O1 H1A 110.3(4) . 4_565 ?
Co1 O1 H1A 110.3 . . ?
Co1 O1 H1B 110.2 . . ?
Co1 O1 H1B 110.2(11) . 4_565 ?
H1A O1 H1A 134.8 . 4_565 ?
H1A O1 H1B 103.7 . . ?
H1A O1 H1B 42.7 . 4_565 ?
H1A O1 H1B 103.7 4_565 4_565 ?
H1B O1 H1A 42.7 . 4_565 ?
H1B O1 H1B 63.5 . 4_565 ?
Co1 O2 H2A 123.4 . . ?
Co1 O2 H2A 123.4(7) . 2_556 ?
Co1 O2 H2B 123.8 . . ?
Co1 O2 H2B 123.8(7) . 2_556 ?
H2A O2 H2A 113.2 . 2_556 ?
H2A O2 H2B 104.5 2_556 2_556 ?
H2A O2 H2B 30.4 . 2_556 ?
H2A O2 H2B 104.5 . . ?
H2B O2 H2A 30.4 . 2_556 ?
H2B O2 H2B 112.4 . 2_556 ?
Co1 O3 H3A 110.1(6) . 4_565 ?
Co1 O3 H3A 110.1 . . ?
Co1 O3 H3B 110.0(11) . 4_565 ?
Co1 O3 H3B 110.0 . . ?
H3A O3 H3A 129.9 . 4_565 ?
H3A O3 H3B 103.8 . . ?
H3A O3 H3B 103.8 4_565 4_565 ?
H3A O3 H3B 33.4 . 4_565 ?
H3B O3 H3A 33.4 . 4_565 ?
H3B O3 H3B 72.7 . 4_565 ?
C1 O4 H4 111(3) . . ?
O4 C1 C2 119.92(16) . . ?
O5 C1 O4 120.94(17) . . ?
O5 C1 C2 119.14(17) . . ?
C2 C2 C1 128.66(10) 4_575 . ?
C3 C2 C1 113.56(16) . . ?
C3 C2 C2 117.78(11) . 4_575 ?
C2 C3 C2 124.4(2) . 2_757 ?
C2 C3 H3 117.8 2_757 . ?
C2 C3 H3 117.8 . . ?

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
O4 C1 C2 C2 -2.7(2) . . . 4_575 ?
O4 C1 C2 C3 176.53(16) . . . . ?
O5 C1 C2 C2 178.60(14) . . . 4_575 ?
O5 C1 C2 C3 -2.2(3) . . . . ?
C1 C2 C3 C2 -179.30(16) . . . 2_757 ?
C2 C2 C3 C2 0.002(0) 4_575 . . 2_757 ?

_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_400K
_database_code_depnum_ccdc_archive 'CCDC 2211958'
_audit_update_record             
;
2022-10-08 deposited with the CCDC.	2022-11-10 downloaded from the CCDC.
;
_audit_creation_date             2022-09-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Co H12 O6, C10 H4 O8'
_chemical_formula_sum            'C10 H16 Co O14'
_chemical_formula_weight         419.16
_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'
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           10
_space_group_name_H-M_alt        'P 1 2/m 1'
_space_group_name_Hall           '-P 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'-x, -y, -z'
'x, -y, z'

_cell_length_a                   6.523(6)
_cell_length_b                   9.909(8)
_cell_length_c                   6.641(7)
_cell_angle_alpha                90
_cell_angle_beta                 115.98(4)
_cell_angle_gamma                90
_cell_volume                     385.9(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1692
_cell_measurement_temperature    400.00
_cell_measurement_theta_max      26.72
_cell_measurement_theta_min      3.66
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.190
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.1988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1839 before and 0.1104 after correction.
The Ratio of minimum to maximum transmission is 0.2666.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.804
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             215
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.963
_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       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6878
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.460
_diffrn_reflns_theta_min         2.055
_diffrn_ambient_temperature      400.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                883
_reflns_number_total             912
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.750
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     71
_refine_ls_number_reflns         912
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0319
_refine_ls_restrained_S_all      1.114
_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)+(0.0525P)²+0.2139P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0893
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 Co1-H2A \\sim Co1-H2B
 with sigma of 0.02
3. Others
 Fixed Sof: H1A(0.5) H1B(0.5) H2A(0.5) H2B(0.5) H3A(0.5) H3B(0.5)
4.a Free rotating group:
 O2(H2A,H2B)
4.b Rotating group:
 O1(H1A,H1B), O3(H3A,H3B)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.000000 0.500000 0.500000 0.02115(19) Uani 1 4 d DS T P . .
O1 O -0.1246(5) 0.500000 0.7422(5) 0.0508(7) Uani 1 2 d S T P . .
H1A H -0.164808 0.580642 0.760655 0.076 Uiso 0.5 1 d R U P . .
H1B H -0.250529 0.454640 0.694903 0.076 Uiso 0.5 1 d R U P . .
O2 O 0.000000 0.2868(2) 0.500000 0.0411(6) Uani 1 2 d GS T P . .
H2A H 0.108320 0.239766 0.594760 0.062 Uiso 0.5 1 d DG U P . .
H2B H -0.118618 0.239273 0.468964 0.062 Uiso 0.5 1 d DG U P . .
O3 O 0.3247(3) 0.500000 0.7530(4) 0.0447(6) Uani 1 2 d S T P . .
H3A H 0.385144 0.421330 0.764962 0.067 Uiso 0.5 1 d R U P . .
H3B H 0.410754 0.551530 0.716792 0.067 Uiso 0.5 1 d R U P . .
O4 O 0.3856(2) 0.88008(15) 0.6995(3) 0.0389(4) Uani 1 1 d . . . . .
O5 O 0.6237(3) 0.71132(14) 0.8060(3) 0.0427(4) Uani 1 1 d . . . . .
C1 C 0.5890(3) 0.83297(19) 0.7927(3) 0.0252(4) Uani 1 1 d . . . . .
C2 C 0.7911(3) 0.92889(17) 0.8933(3) 0.0204(4) Uani 1 1 d . . . . .
C3 C 1.000000 0.8635(2) 1.000000 0.0220(5) Uani 1 2 d S T P . .
H3 H 1.000000 0.769692 1.000000 0.026 Uiso 1 2 calc R U P . .
H4 H 0.388(9) 1.000000 0.707(8) 0.065(14) Uiso 1 2 d S . 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
Co1 O1 2.096(3) . ?
Co1 O1 2.096(3) 3_566 ?
Co1 O2 2.112(3) . ?
Co1 O2 2.112(3) 3_566 ?
Co1 O3 2.047(3) 3_566 ?
Co1 O3 2.047(3) . ?
O1 H1A 0.867(16) 4_565 ?
O1 H1A 0.8665 . ?
O1 H1B 0.87(4) 4_565 ?
O1 H1B 0.8658 . ?
O2 H2A 0.85(3) 2_556 ?
O2 H2A 0.8505 . ?
O2 H2B 0.8506 . ?
O2 H2B 0.85(3) 2_556 ?
O3 H3A 0.86(2) 4_565 ?
O3 H3A 0.8613 . ?
O3 H3B 0.8670 . ?
O3 H3B 0.87(5) 4_565 ?
O4 C1 1.281(3) . ?
O4 H4 1.189(3) . ?
O5 C1 1.223(3) . ?
C1 C2 1.522(3) . ?
C2 C2 1.409(3) 4_575 ?
C2 C3 1.390(2) . ?
C3 H3 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
O1 Co1 O1 180.00(6) . 3_566 ?
O1 Co1 O2 90.0 3_566 3_566 ?
O1 Co1 O2 90.0 3_566 . ?
O1 Co1 O2 90.0 . 3_566 ?
O1 Co1 O2 90.000(1) . . ?
O2 Co1 O2 180.0 . 3_566 ?
O3 Co1 O1 88.84(15) . . ?
O3 Co1 O1 91.16(15) 3_566 . ?
O3 Co1 O1 88.84(15) 3_566 3_566 ?
O3 Co1 O1 91.16(15) . 3_566 ?
O3 Co1 O2 90.0 3_566 . ?
O3 Co1 O2 90.0 3_566 3_566 ?
O3 Co1 O2 90.0 . 3_566 ?
O3 Co1 O2 90.0 . . ?
O3 Co1 O3 180.0 3_566 . ?
Co1 O1 H1A 110.6 . . ?
Co1 O1 H1A 110.6(4) . 4_565 ?
Co1 O1 H1B 110.3(11) . 4_565 ?
Co1 O1 H1B 110.3 . . ?
H1A O1 H1A 134.5 . 4_565 ?
H1A O1 H1B 103.4 4_565 4_565 ?
H1A O1 H1B 43.5 . 4_565 ?
H1A O1 H1B 103.4 . . ?
H1B O1 H1A 43.5 . 4_565 ?
H1B O1 H1B 62.6 . 4_565 ?
Co1 O2 H2A 123.3(8) . 2_556 ?
Co1 O2 H2A 123.3 . . ?
Co1 O2 H2B 123.7(7) . 2_556 ?
Co1 O2 H2B 123.7 . . ?
H2A O2 H2A 113.5 . 2_556 ?
H2A O2 H2B 31.1 . 2_556 ?
H2A O2 H2B 104.4 2_556 2_556 ?
H2A O2 H2B 104.4 . . ?
H2B O2 H2A 31.1 . 2_556 ?
H2B O2 H2B 112.7 . 2_556 ?
Co1 O3 H3A 110.0 . . ?
Co1 O3 H3A 110.0(6) . 4_565 ?
Co1 O3 H3B 109.6(11) . 4_565 ?
Co1 O3 H3B 109.6 . . ?
H3A O3 H3A 129.7 . 4_565 ?
H3A O3 H3B 103.5 . . ?
H3A O3 H3B 33.6 . 4_565 ?
H3A O3 H3B 103.5 4_565 4_565 ?
H3B O3 H3A 33.6 . 4_565 ?
H3B O3 H3B 72.2 . 4_565 ?
C1 O4 H4 111(3) . . ?
O4 C1 C2 119.94(17) . . ?
O5 C1 O4 120.93(17) . . ?
O5 C1 C2 119.11(17) . . ?
C2 C2 C1 128.64(10) 4_575 . ?
C3 C2 C1 113.58(17) . . ?
C3 C2 C2 117.77(12) . 4_575 ?
C2 C3 C2 124.5(2) . 2_757 ?
C2 C3 H3 117.8 . . ?
C2 C3 H3 117.8 2_757 . ?

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
O4 C1 C2 C2 -2.7(2) . . . 4_575 ?
O4 C1 C2 C3 176.47(16) . . . . ?
O5 C1 C2 C2 178.59(15) . . . 4_575 ?
O5 C1 C2 C3 -2.2(3) . . . . ?
C1 C2 C3 C2 -179.29(16) . . . 2_757 ?
C2 C2 C3 C2 0.000(0) 4_575 . . 2_757 ?

_olex2_submission_special_instructions 'No special instructions were received'
