# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_Co1
_database_code_depnum_ccdc_archive 'CCDC 2374155'
_audit_update_record             
;
2024-07-28 deposited with the CCDC.	2024-09-25 downloaded from the CCDC.
;
_audit_creation_date             2024-07-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H10 Co N2 O7, 2(H2 O)'
_chemical_formula_sum            'C9 H14 Co N2 O9'
_chemical_formula_weight         353.15
_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      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                   7.4824(3)
_cell_length_b                   8.4218(4)
_cell_length_c                   11.4038(6)
_cell_angle_alpha                80.323(2)
_cell_angle_beta                 73.083(2)
_cell_angle_gamma                67.581(2)
_cell_volume                     634.23(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9929
_cell_measurement_temperature    253.00
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      3.15
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.405
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.849
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             362
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            28114
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.513
_diffrn_reflns_theta_min         3.041
_diffrn_ambient_temperature      253.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.987
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2771
_reflns_number_total             2879
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         1.366
_refine_diff_density_min         -0.844
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2879
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0361
_refine_ls_restrained_S_all      1.092
_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)+(0.0521P)²+1.2063P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1069
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H9A,H9B} of O9
 At 1.5 times of:
  {H3A,H3B} of O3, {H2A,H2B} of O2, {H5A,H5B} of O5, {H4A,H4B} of O4
2. Restrained distances
 Co1-H2A \\sim Co1-H2B
 with sigma of 0.02
 Co1-H4A \\sim Co1-H4B
 with sigma of 0.02
 Co1-H3A \\sim Co1-H3B
 with sigma of 0.02
3.a Riding coordinates:
 O9(H9A,H9B)
3.b Free rotating group:
 O2(H2A,H2B), O3(H3A,H3B), O4(H4A,H4B), O5(H5A,H5B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C7(H7)
;
_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 0.27591(5) 0.71838(4) 0.82879(3) 0.01769(13) Uani 1 1 d D . . . .
O1 O 0.2095(3) 0.6454(2) 0.68861(16) 0.0212(4) Uani 1 1 d . . . . .
O2 O 0.0014(3) 0.7138(3) 0.94303(17) 0.0251(4) Uani 1 1 d G . . . .
H2A H -0.011300 0.684113 1.020097 0.038 Uiso 1 1 d DG U . . .
H2B H -0.063888 0.664771 0.920233 0.038 Uiso 1 1 d DG U . . .
O3 O 0.1260(4) 0.9743(2) 0.7801(2) 0.0355(5) Uani 1 1 d G . . . .
H3A H 0.070080 1.001965 0.719912 0.053 Uiso 1 1 d DG U . . .
H3B H 0.151355 1.063500 0.786195 0.053 Uiso 1 1 d DG U . . .
O4 O 0.5350(3) 0.7514(3) 0.7266(2) 0.0393(5) Uani 1 1 d G . . . .
H4A H 0.644101 0.703672 0.749964 0.059 Uiso 1 1 d DG U . . .
H4B H 0.538640 0.849842 0.692962 0.059 Uiso 1 1 d DG U . . .
O6 O -0.0090(4) 0.8834(3) 0.6206(2) 0.0374(5) Uani 1 1 d . . . . .
O7 O 0.1597(3) 0.4330(2) 0.17547(16) 0.0218(4) Uani 1 1 d . . . . .
O8 O -0.0642(3) 0.6983(2) 0.19090(17) 0.0278(4) Uani 1 1 d . . . . .
N1 N 0.3632(3) 0.7272(3) 0.99142(19) 0.0191(4) Uani 1 1 d . . . . .
N2 N 0.5566(3) 0.5496(3) 1.12832(19) 0.0194(4) Uani 1 1 d . . . . .
C1 C 0.4780(3) 0.5765(3) 1.0329(2) 0.0164(4) Uani 1 1 d . . . . .
C2 C 0.3233(4) 0.8648(3) 1.0518(3) 0.0256(5) Uani 1 1 d . . . . .
H2 H 0.242458 0.973516 1.025649 0.031 Uiso 1 1 calc R U . . .
C3 C 0.3989(4) 0.8501(4) 1.1518(3) 0.0301(6) Uani 1 1 d . . . . .
H3 H 0.370833 0.947110 1.193817 0.036 Uiso 1 1 calc R U . . .
C4 C 0.5167(4) 0.6887(3) 1.1881(2) 0.0257(5) Uani 1 1 d . . . . .
H4 H 0.570015 0.675828 1.255785 0.031 Uiso 1 1 calc R U . . .
C5 C 0.0784(4) 0.7250(3) 0.6287(2) 0.0192(5) Uani 1 1 d . . . . .
C6 C 0.0310(4) 0.6115(3) 0.5626(2) 0.0176(4) Uani 1 1 d . . . . .
C7 C 0.0382(4) 0.6454(3) 0.4379(2) 0.0185(5) Uani 1 1 d . . . . .
H7 H 0.063328 0.743886 0.396256 0.022 Uiso 1 1 calc R U . . .
C8 C 0.0085(4) 0.5336(3) 0.3747(2) 0.0175(4) Uani 1 1 d . . . . .
C9 C 0.0345(4) 0.5587(3) 0.2369(2) 0.0183(4) Uani 1 1 d . . . . .
O5 O 0.3942(5) 0.9756(4) 0.4191(3) 0.0624(8) Uani 1 1 d G . . . .
H5A H 0.267201 1.006859 0.429527 0.094 Uiso 1 1 d G U . . .
H5B H 0.447920 0.866211 0.412133 0.094 Uiso 1 1 d G U . . .
O9 O 0.5076(14) 0.6392(12) 0.4688(8) 0.208(4) Uiso 1 1 d . . . . .
H9A H 0.442751 0.657150 0.413895 0.249 Uiso 1 1 d R U . . .
H9B H 0.575731 0.530709 0.468995 0.249 Uiso 1 1 d 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 O1 2.0508(17) . ?
Co1 O2 2.0985(19) . ?
Co1 O3 2.0802(19) . ?
Co1 O4 2.045(2) . ?
Co1 N1 2.159(2) . ?
Co1 N2 2.175(2) 2_667 ?
O1 C5 1.270(3) . ?
O2 H2A 0.8600 . ?
O2 H2B 0.8605 . ?
O3 H3A 0.8596 . ?
O3 H3B 0.8602 . ?
O4 H4A 0.8598 . ?
O4 H4B 0.8599 . ?
O6 C5 1.243(3) . ?
O7 C9 1.265(3) . ?
O8 C9 1.249(3) . ?
N1 C1 1.333(3) . ?
N1 C2 1.338(3) . ?
N2 C1 1.330(3) . ?
N2 C4 1.346(3) . ?
C1 C1 1.479(4) 2_667 ?
C2 H2 0.9400 . ?
C2 C3 1.382(4) . ?
C3 H3 0.9400 . ?
C3 C4 1.381(4) . ?
C4 H4 0.9400 . ?
C5 C6 1.504(3) . ?
C6 C7 1.392(3) . ?
C6 C8 1.397(3) 2_566 ?
C7 H7 0.9400 . ?
C7 C8 1.391(3) . ?
C8 C9 1.514(3) . ?
O5 H5A 0.8601 . ?
O5 H5B 0.8600 . ?
O9 H9A 0.8599 . ?
O9 H9B 0.8600 . ?

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 O2 88.75(7) . . ?
O1 Co1 O3 89.25(7) . . ?
O1 Co1 N1 165.48(8) . . ?
O1 Co1 N2 89.76(7) . 2_667 ?
O2 Co1 N1 88.13(8) . . ?
O2 Co1 N2 95.21(8) . 2_667 ?
O3 Co1 O2 87.27(9) . . ?
O3 Co1 N1 104.76(8) . . ?
O3 Co1 N2 177.31(9) . 2_667 ?
O4 Co1 O1 96.37(9) . . ?
O4 Co1 O2 172.82(9) . . ?
O4 Co1 O3 87.78(10) . . ?
O4 Co1 N1 88.11(9) . . ?
O4 Co1 N2 89.85(9) . 2_667 ?
N1 Co1 N2 76.41(8) . 2_667 ?
C5 O1 Co1 131.23(16) . . ?
Co1 O2 H2A 120.9 . . ?
Co1 O2 H2B 119.6 . . ?
H2A O2 H2B 104.5 . . ?
Co1 O3 H3A 121.4 . . ?
Co1 O3 H3B 128.1 . . ?
H3A O3 H3B 104.5 . . ?
Co1 O4 H4A 121.3 . . ?
Co1 O4 H4B 122.3 . . ?
H4A O4 H4B 104.5 . . ?
C1 N1 Co1 115.00(15) . . ?
C1 N1 C2 116.7(2) . . ?
C2 N1 Co1 128.23(17) . . ?
C1 N2 Co1 114.84(16) . 2_667 ?
C1 N2 C4 116.6(2) . . ?
C4 N2 Co1 128.55(17) . 2_667 ?
N1 C1 C1 117.1(3) . 2_667 ?
N2 C1 N1 126.4(2) . . ?
N2 C1 C1 116.5(3) . 2_667 ?
N1 C2 H2 119.4 . . ?
N1 C2 C3 121.2(2) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 121.0 . . ?
C4 C3 C2 118.0(2) . . ?
C4 C3 H3 121.0 . . ?
N2 C4 C3 121.1(2) . . ?
N2 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
O1 C5 C6 114.8(2) . . ?
O6 C5 O1 125.9(2) . . ?
O6 C5 C6 119.4(2) . . ?
C7 C6 C5 120.1(2) . . ?
C7 C6 C8 120.2(2) . 2_566 ?
C8 C6 C5 119.6(2) 2_566 . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.2(2) . . ?
C8 C7 H7 119.9 . . ?
C6 C8 C9 119.1(2) 2_566 . ?
C7 C8 C6 119.6(2) . 2_566 ?
C7 C8 C9 121.1(2) . . ?
O7 C9 C8 116.1(2) . . ?
O8 C9 O7 124.2(2) . . ?
O8 C9 C8 119.6(2) . . ?
H5A O5 H5B 109.5 . . ?
H9A O9 H9B 104.5 . . ?

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
Co1 O1 C5 O6 19.6(4) . . . . ?
Co1 O1 C5 C6 -160.80(16) . . . . ?
Co1 N1 C1 N2 177.42(19) . . . . ?
Co1 N1 C1 C1 -3.0(3) . . . 2_667 ?
Co1 N1 C2 C3 -176.7(2) . . . . ?
Co1 N2 C1 N1 177.19(19) 2_667 . . . ?
Co1 N2 C1 C1 -2.4(3) 2_667 . . 2_667 ?
Co1 N2 C4 C3 -176.8(2) 2_667 . . . ?
O1 C5 C6 C7 -127.6(2) . . . . ?
O1 C5 C6 C8 48.5(3) . . . 2_566 ?
O6 C5 C6 C7 52.0(4) . . . . ?
O6 C5 C6 C8 -131.8(3) . . . 2_566 ?
N1 C2 C3 C4 -0.2(4) . . . . ?
C1 N1 C2 C3 0.2(4) . . . . ?
C1 N2 C4 C3 0.4(4) . . . . ?
C2 N1 C1 N2 0.1(4) . . . . ?
C2 N1 C1 C1 179.7(3) . . . 2_667 ?
C2 C3 C4 N2 -0.2(4) . . . . ?
C4 N2 C1 N1 -0.4(4) . . . . ?
C4 N2 C1 C1 180.0(3) . . . 2_667 ?
C5 C6 C7 C8 175.4(2) . . . . ?
C6 C7 C8 C6 0.7(4) . . . 2_566 ?
C6 C7 C8 C9 -174.3(2) . . . . ?
C6 C8 C9 O7 -52.2(3) 2_566 . . . ?
C6 C8 C9 O8 128.4(3) 2_566 . . . ?
C7 C8 C9 O7 122.8(3) . . . . ?
C7 C8 C9 O8 -56.6(3) . . . . ?
C8 C6 C7 C8 -0.7(4) 2_566 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT415_Co1                 
;
PROBLEM: Short Inter D-H..H-X       H4       ..H9A      .       1.79 Ang.  
RESPONSE: It is very difficult to locate hydrogen atoms accurately using X-ray
data because these atoms have low scattering power.
;
_vrf_PLAT417_Co1                 
;
PROBLEM: Short Inter D-H..H-D       H5B      ..H9A      .       1.77 Ang.  
RESPONSE: It is very difficult to locate hydrogen atoms accurately using X-ray
data because these atoms have low scattering power.
;
_vrf_PLAT420_Co1                 
;
PROBLEM: D-H Bond Without Acceptor  O9       --H9A      .     Please Check 
RESPONSE: It is very difficult to locate hydrogen atoms accurately using X-ray
data because these atoms have low scattering power.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_Co3
_database_code_depnum_ccdc_archive 'CCDC 2374157'
_audit_update_record             
;
2024-07-28 deposited with the CCDC.	2024-09-25 downloaded from the CCDC.
;
_audit_creation_date             2024-07-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H9 Co N4 O8'
_chemical_formula_sum            'C18 H9 Co N4 O8'
_chemical_formula_weight         468.22
_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      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                   8.5279(8)
_cell_length_b                   9.8241(9)
_cell_length_c                   11.5691(8)
_cell_angle_alpha                110.011(3)
_cell_angle_beta                 94.217(3)
_cell_angle_gamma                107.725(3)
_cell_volume                     850.22(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2551
_cell_measurement_temperature    190.00
_cell_measurement_theta_max      26.23
_cell_measurement_theta_min      2.36
_shelx_estimated_absorpt_T_max   0.938
_shelx_estimated_absorpt_T_min   0.873
_exptl_absorpt_coefficient_mu    1.073
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.829
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0914
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_Laue_measured_fraction_full 1.000
_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       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19142
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.409
_diffrn_reflns_theta_min         2.357
_diffrn_ambient_temperature      190.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2834
_reflns_number_total             3490
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.725
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3490
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.082
_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)+(0.0350P)²+0.5717P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0973
_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) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C15(H15), C17(H17)
2.b Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_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 0.89423(5) 0.67304(4) 0.87704(4) 0.01442(12) Uani 1 1 d . . . . .
O1 O 0.0858(3) 0.4534(2) 0.29929(19) 0.0214(5) Uani 1 1 d . . . . .
O2 O 0.6577(3) 0.9012(2) 0.9020(2) 0.0234(5) Uani 1 1 d . . . . .
O3 O 0.3962(3) 0.3326(3) 0.5850(2) 0.0304(6) Uani 1 1 d . . . . .
H3 H 0.392123 0.259426 0.608048 0.046 Uiso 1 1 calc R U . . .
O4 O 0.6607(3) 0.6601(2) 0.8155(2) 0.0207(5) Uani 1 1 d . . . . .
O5 O 0.4172(3) 1.0887(2) 0.6315(2) 0.0250(5) Uani 1 1 d . . . . .
O6 O 0.3226(3) 0.4321(2) 0.7692(2) 0.0221(5) Uani 1 1 d . . . . .
O7 O 0.1047(3) 0.6877(3) 0.3119(2) 0.0318(6) Uani 1 1 d . . . . .
O8 O 0.2251(3) 0.9491(3) 0.4596(2) 0.0278(5) Uani 1 1 d . . . . .
N1 N 0.9982(3) 0.8781(3) 0.8431(2) 0.0155(5) Uani 1 1 d . . . . .
N2 N 0.7963(3) 0.4840(3) 0.9314(2) 0.0162(5) Uani 1 1 d . . . . .
N3 N 1.0668(3) 1.1500(3) 0.9404(2) 0.0152(5) Uani 1 1 d . . . . .
N4 N 0.8799(3) 0.3410(3) 1.0372(2) 0.0148(5) Uani 1 1 d . . . . .
C1 C 0.4677(4) 0.7274(3) 0.7106(3) 0.0159(6) Uani 1 1 d . . . . .
C2 C 0.6063(4) 0.7698(3) 0.8206(3) 0.0159(6) Uani 1 1 d . . . . .
C3 C 0.1366(4) 0.5971(3) 0.3583(3) 0.0181(6) Uani 1 1 d . . . . .
C4 C 0.3673(4) 0.5749(3) 0.6374(3) 0.0152(6) Uani 1 1 d . . . . .
C5 C 0.2610(4) 0.5440(3) 0.5277(3) 0.0174(6) Uani 1 1 d . . . . .
H5 H 0.196199 0.439316 0.476644 0.021 Uiso 1 1 calc R U . . .
C6 C 0.7190(4) 0.2504(3) 1.0167(3) 0.0191(6) Uani 1 1 d . . . . .
H6 H 0.691819 0.169451 1.047182 0.023 Uiso 1 1 calc R U . . .
C7 C 0.6357(4) 0.3933(3) 0.9123(3) 0.0194(6) Uani 1 1 d . . . . .
H7 H 0.550213 0.412744 0.870114 0.023 Uiso 1 1 calc R U . . .
C8 C 1.0181(3) 1.0075(3) 0.9408(3) 0.0135(6) Uani 1 1 d . . . . .
C9 C 0.2451(4) 0.6601(3) 0.4890(3) 0.0157(6) Uani 1 1 d . . . . .
C10 C 0.3373(4) 0.8156(3) 0.5681(3) 0.0164(6) Uani 1 1 d . . . . .
C11 C 1.0206(4) 0.8921(4) 0.7340(3) 0.0195(6) Uani 1 1 d . . . . .
H11 H 1.007850 0.802376 0.662499 0.023 Uiso 1 1 calc R U . . .
C12 C 0.4479(4) 0.8443(3) 0.6756(3) 0.0166(6) Uani 1 1 d . . . . .
H12 H 0.513059 0.948649 0.727388 0.020 Uiso 1 1 calc R U . . .
C13 C 1.0618(4) 1.0335(4) 0.7225(3) 0.0202(7) Uani 1 1 d . . . . .
H13 H 1.072256 1.042029 0.643895 0.024 Uiso 1 1 calc R U . . .
C14 C 0.9111(4) 0.4523(3) 0.9914(3) 0.0145(6) Uani 1 1 d . . . . .
C15 C 1.0873(4) 1.1621(4) 0.8302(3) 0.0196(6) Uani 1 1 d . . . . .
H15 H 1.120229 1.261511 0.825984 0.023 Uiso 1 1 calc R U . . .
C16 C 0.3296(4) 0.9613(3) 0.5526(3) 0.0175(6) Uani 1 1 d . . . . .
C17 C 0.5918(4) 0.2721(4) 0.9524(3) 0.0203(6) Uani 1 1 d . . . . .
H17 H 0.478193 0.205955 0.936335 0.024 Uiso 1 1 calc R U . . .
C18 C 0.3624(4) 0.4404(3) 0.6732(3) 0.0180(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O1 2.044(2) 2_666 ?
Co1 O4 2.016(2) . ?
Co1 N1 2.122(2) . ?
Co1 N2 2.115(2) . ?
Co1 N3 2.151(2) 2_777 ?
Co1 N4 2.165(2) 2_767 ?
O1 C3 1.253(4) . ?
O2 C2 1.228(4) . ?
O3 H3 0.8400 . ?
O3 C18 1.317(4) . ?
O4 C2 1.283(3) . ?
O5 C16 1.227(4) . ?
O6 C18 1.207(4) . ?
O7 C3 1.267(4) . ?
O8 C16 1.292(4) . ?
N1 C8 1.333(4) . ?
N1 C11 1.337(4) . ?
N2 C7 1.340(4) . ?
N2 C14 1.331(4) . ?
N3 C8 1.335(4) . ?
N3 C15 1.339(4) . ?
N4 C6 1.340(4) . ?
N4 C14 1.337(4) . ?
C1 C2 1.518(4) . ?
C1 C4 1.392(4) . ?
C1 C12 1.393(4) . ?
C3 C9 1.527(4) . ?
C4 C5 1.386(4) . ?
C4 C18 1.505(4) . ?
C5 H5 0.9500 . ?
C5 C9 1.398(4) . ?
C6 H6 0.9500 . ?
C6 C17 1.380(4) . ?
C7 H7 0.9500 . ?
C7 C17 1.381(4) . ?
C8 C8 1.472(5) 2_777 ?
C9 C10 1.413(4) . ?
C10 C12 1.393(4) . ?
C10 C16 1.522(4) . ?
C11 H11 0.9500 . ?
C11 C13 1.381(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C13 C15 1.383(4) . ?
C14 C14 1.477(6) 2_767 ?
C15 H15 0.9500 . ?
C17 H17 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 N1 89.26(9) 2_666 . ?
O1 Co1 N2 96.65(9) 2_666 . ?
O1 Co1 N3 164.72(9) 2_666 2_777 ?
O1 Co1 N4 92.40(9) 2_666 2_767 ?
O4 Co1 O1 92.20(9) . 2_666 ?
O4 Co1 N1 90.33(9) . . ?
O4 Co1 N2 91.10(9) . . ?
O4 Co1 N3 96.31(9) . 2_777 ?
O4 Co1 N4 168.54(9) . 2_767 ?
N1 Co1 N3 78.05(9) . 2_777 ?
N1 Co1 N4 100.22(9) . 2_767 ?
N2 Co1 N1 173.86(9) . . ?
N2 Co1 N3 95.86(9) . 2_777 ?
N2 Co1 N4 77.94(9) . 2_767 ?
N3 Co1 N4 81.66(9) 2_777 2_767 ?
C3 O1 Co1 130.07(19) . 2_666 ?
C18 O3 H3 109.5 . . ?
C2 O4 Co1 129.05(19) . . ?
C8 N1 Co1 113.86(18) . . ?
C8 N1 C11 116.8(2) . . ?
C11 N1 Co1 128.4(2) . . ?
C7 N2 Co1 128.4(2) . . ?
C14 N2 Co1 114.72(19) . . ?
C14 N2 C7 116.9(2) . . ?
C8 N3 Co1 113.10(18) . 2_777 ?
C8 N3 C15 116.8(3) . . ?
C15 N3 Co1 130.1(2) . 2_777 ?
C6 N4 Co1 130.07(19) . 2_767 ?
C14 N4 Co1 113.10(19) . 2_767 ?
C14 N4 C6 116.7(3) . . ?
C4 C1 C2 122.6(2) . . ?
C4 C1 C12 118.3(3) . . ?
C12 C1 C2 118.8(3) . . ?
O2 C2 O4 126.6(3) . . ?
O2 C2 C1 119.4(3) . . ?
O4 C2 C1 114.0(3) . . ?
O1 C3 O7 122.5(3) . . ?
O1 C3 C9 116.6(2) . . ?
O7 C3 C9 120.8(3) . . ?
C1 C4 C18 123.4(3) . . ?
C5 C4 C1 119.1(3) . . ?
C5 C4 C18 117.5(3) . . ?
C4 C5 H5 118.6 . . ?
C4 C5 C9 122.9(3) . . ?
C9 C5 H5 118.6 . . ?
N4 C6 H6 119.2 . . ?
N4 C6 C17 121.6(3) . . ?
C17 C6 H6 119.2 . . ?
N2 C7 H7 119.3 . . ?
N2 C7 C17 121.5(3) . . ?
C17 C7 H7 119.3 . . ?
N1 C8 N3 125.7(3) . . ?
N1 C8 C8 117.4(3) . 2_777 ?
N3 C8 C8 116.9(3) . 2_777 ?
C5 C9 C3 113.2(3) . . ?
C5 C9 C10 118.0(3) . . ?
C10 C9 C3 128.5(3) . . ?
C9 C10 C16 127.8(3) . . ?
C12 C10 C9 118.2(3) . . ?
C12 C10 C16 113.9(3) . . ?
N1 C11 H11 119.1 . . ?
N1 C11 C13 121.7(3) . . ?
C13 C11 H11 119.1 . . ?
C1 C12 C10 123.2(3) . . ?
C1 C12 H12 118.4 . . ?
C10 C12 H12 118.4 . . ?
C11 C13 H13 121.4 . . ?
C11 C13 C15 117.3(3) . . ?
C15 C13 H13 121.4 . . ?
N2 C14 N4 125.8(3) . . ?
N2 C14 C14 117.3(3) . 2_767 ?
N4 C14 C14 116.8(3) . 2_767 ?
N3 C15 C13 121.6(3) . . ?
N3 C15 H15 119.2 . . ?
C13 C15 H15 119.2 . . ?
O5 C16 O8 120.9(3) . . ?
O5 C16 C10 119.6(3) . . ?
O8 C16 C10 119.5(3) . . ?
C6 C17 C7 117.5(3) . . ?
C6 C17 H17 121.2 . . ?
C7 C17 H17 121.2 . . ?
O3 C18 C4 112.1(2) . . ?
O6 C18 O3 125.4(3) . . ?
O6 C18 C4 122.4(3) . . ?

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 O1 C3 O7 51.1(4) 2_666 . . . ?
Co1 O1 C3 C9 -126.9(2) 2_666 . . . ?
Co1 O4 C2 O2 -31.2(4) . . . . ?
Co1 O4 C2 C1 147.2(2) . . . . ?
Co1 N1 C8 N3 -173.8(2) . . . . ?
Co1 N1 C8 C8 5.6(4) . . . 2_777 ?
Co1 N1 C11 C13 168.2(2) . . . . ?
Co1 N2 C7 C17 179.1(2) . . . . ?
Co1 N2 C14 N4 178.4(2) . . . . ?
Co1 N2 C14 C14 -1.8(4) . . . 2_767 ?
Co1 N3 C8 N1 -174.3(2) 2_777 . . . ?
Co1 N3 C8 C8 6.2(4) 2_777 . . 2_777 ?
Co1 N3 C15 C13 177.4(2) 2_777 . . . ?
Co1 N4 C6 C17 -175.5(2) 2_767 . . . ?
Co1 N4 C14 N2 178.3(2) 2_767 . . . ?
Co1 N4 C14 C14 -1.4(4) 2_767 . . 2_767 ?
O1 C3 C9 C5 -4.7(4) . . . . ?
O1 C3 C9 C10 170.4(3) . . . . ?
O7 C3 C9 C5 177.2(3) . . . . ?
O7 C3 C9 C10 -7.7(5) . . . . ?
N1 C11 C13 C15 3.1(4) . . . . ?
N2 C7 C17 C6 2.0(5) . . . . ?
N4 C6 C17 C7 -1.5(5) . . . . ?
C1 C4 C5 C9 -2.4(4) . . . . ?
C1 C4 C18 O3 -124.5(3) . . . . ?
C1 C4 C18 O6 59.3(4) . . . . ?
C2 C1 C4 C5 -170.3(3) . . . . ?
C2 C1 C4 C18 12.1(4) . . . . ?
C2 C1 C12 C10 172.7(3) . . . . ?
C3 C9 C10 C12 -170.3(3) . . . . ?
C3 C9 C10 C16 10.9(5) . . . . ?
C4 C1 C2 O2 -159.4(3) . . . . ?
C4 C1 C2 O4 22.1(4) . . . . ?
C4 C1 C12 C10 -2.6(4) . . . . ?
C4 C5 C9 C3 173.3(3) . . . . ?
C4 C5 C9 C10 -2.4(4) . . . . ?
C5 C4 C18 O3 57.9(4) . . . . ?
C5 C4 C18 O6 -118.4(3) . . . . ?
C5 C9 C10 C12 4.6(4) . . . . ?
C5 C9 C10 C16 -174.2(3) . . . . ?
C6 N4 C14 N2 2.5(4) . . . . ?
C6 N4 C14 C14 -177.2(3) . . . 2_767 ?
C7 N2 C14 N4 -2.1(4) . . . . ?
C7 N2 C14 C14 177.7(3) . . . 2_767 ?
C8 N1 C11 C13 -0.2(4) . . . . ?
C8 N3 C15 C13 -1.0(4) . . . . ?
C9 C10 C12 C1 -2.2(4) . . . . ?
C9 C10 C16 O5 179.0(3) . . . . ?
C9 C10 C16 O8 2.3(5) . . . . ?
C11 N1 C8 N3 -3.8(4) . . . . ?
C11 N1 C8 C8 175.7(3) . . . 2_777 ?
C11 C13 C15 N3 -2.5(4) . . . . ?
C12 C1 C2 O2 25.6(4) . . . . ?
C12 C1 C2 O4 -152.9(3) . . . . ?
C12 C1 C4 C5 4.8(4) . . . . ?
C12 C1 C4 C18 -172.8(3) . . . . ?
C12 C10 C16 O5 0.1(4) . . . . ?
C12 C10 C16 O8 -176.6(3) . . . . ?
C14 N2 C7 C17 -0.3(4) . . . . ?
C14 N4 C6 C17 -0.6(4) . . . . ?
C15 N3 C8 N1 4.3(4) . . . . ?
C15 N3 C8 C8 -175.1(3) . . . 2_777 ?
C16 C10 C12 C1 176.8(3) . . . . ?
C18 C4 C5 C9 175.3(3) . . . . ?

_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_Co2
_database_code_depnum_ccdc_archive 'CCDC 2374156'
_audit_update_record             
;
2024-07-28 deposited with the CCDC.	2024-09-25 downloaded from the CCDC.
;
_audit_creation_date             2024-07-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H8 Co N2 O6, C3 H7 N O, H2 O'
_chemical_formula_sum            'C12 H17 Co N3 O8'
_chemical_formula_weight         390.21
_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.0964(5)
_cell_length_b                   15.9359(6)
_cell_length_c                   7.9797(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.6700(10)
_cell_angle_gamma                90
_cell_volume                     1511.63(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9248
_cell_measurement_temperature    250.00
_cell_measurement_theta_max      26.86
_cell_measurement_theta_min      2.90
_shelx_estimated_absorpt_T_max   0.871
_shelx_estimated_absorpt_T_min   0.689
_exptl_absorpt_coefficient_mu    1.185
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0767
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            37574
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.522
_diffrn_reflns_theta_min         2.137
_diffrn_ambient_temperature      250.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2819
_reflns_number_total             3480
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.462
_refine_diff_density_min         -0.811
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3480
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0452
_refine_ls_restrained_S_all      1.044
_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)+(0.0645P)²+2.9936P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1300
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O8(H8A,H8B)
2.b Rotating group:
 O2(H2A,H2B), O3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8), C9(H9)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C)
;
_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 0.31756(3) 0.40262(2) 0.59184(5) 0.01728(14) Uani 1 1 d . . . . .
O1 O 0.20829(19) 0.44643(13) 0.3783(3) 0.0230(5) Uani 1 1 d . . . . .
O2 O 0.2740(2) 0.27807(13) 0.5287(3) 0.0254(5) Uani 1 1 d . . . . .
H2A H 0.226571 0.276706 0.433829 0.038 Uiso 1 1 d R U . . .
H2B H 0.237539 0.257657 0.602318 0.038 Uiso 1 1 d R U . . .
O3 O 0.42499(19) 0.36096(14) 0.8133(3) 0.0233(5) Uani 1 1 d . . . . .
H3A H 0.399388 0.377469 0.901381 0.035 Uiso 1 1 d R U . . .
H3B H 0.489047 0.385585 0.821948 0.035 Uiso 1 1 d R U . . .
O4 O -0.19314(19) 0.57471(16) 0.2678(3) 0.0274(5) Uani 1 1 d . . . . .
O5 O -0.2889(2) 0.56776(17) 0.0014(3) 0.0327(6) Uani 1 1 d . . . . .
O6 O 0.1692(2) 0.32976(14) 0.2242(3) 0.0308(5) Uani 1 1 d . . . . .
N1 N 0.4489(2) 0.39701(15) 0.4402(3) 0.0192(5) Uani 1 1 d . . . . .
N2 N 0.5995(2) 0.47575(15) 0.3659(3) 0.0201(5) Uani 1 1 d . . . . .
C1 C -0.0954(3) 0.53308(19) 0.0519(4) 0.0194(6) Uani 1 1 d . . . . .
C2 C 0.5584(3) 0.3402(2) 0.2495(5) 0.0319(8) Uani 1 1 d . . . . .
H2 H 0.573853 0.296339 0.178589 0.038 Uiso 1 1 calc R U . . .
C3 C 0.4724(3) 0.3339(2) 0.3395(4) 0.0271(7) Uani 1 1 d . . . . .
H3 H 0.428892 0.284694 0.330723 0.033 Uiso 1 1 calc R U . . .
C4 C 0.5134(3) 0.46475(17) 0.4464(4) 0.0178(6) Uani 1 1 d . . . . .
C6 C 0.0816(3) 0.45721(18) 0.1176(4) 0.0199(6) Uani 1 1 d . . . . .
C7 C 0.6213(3) 0.4129(2) 0.2664(4) 0.0275(7) Uani 1 1 d . . . . .
H7 H 0.680981 0.418331 0.206536 0.033 Uiso 1 1 calc R U . . .
C8 C -0.0135(3) 0.49118(19) 0.1662(4) 0.0208(6) Uani 1 1 d . . . . .
H8 H -0.022578 0.485601 0.280115 0.025 Uiso 1 1 calc R U . . .
C10 C -0.2005(3) 0.56200(19) 0.1106(4) 0.0204(6) Uani 1 1 d . . . . .
C12 C 0.1615(3) 0.40695(19) 0.2483(4) 0.0198(6) Uani 1 1 d . . . . .
O7 O 0.2816(6) 0.6768(4) 0.3595(9) 0.129(2) Uani 1 1 d . . . . .
N3 N 0.1220(5) 0.7079(4) 0.4475(8) 0.0841(16) Uani 1 1 d . . . . .
C9 C 0.1961(5) 0.6428(5) 0.3973(7) 0.0785(19) Uani 1 1 d . . . . .
H9 H 0.181477 0.584856 0.394050 0.094 Uiso 1 1 calc R U . . .
C11 C 0.0106(7) 0.6847(5) 0.4672(15) 0.128(4) Uani 1 1 d . . . . .
H11A H -0.041330 0.694373 0.360856 0.192 Uiso 1 1 calc R U . . .
H11B H -0.011654 0.718323 0.556700 0.192 Uiso 1 1 calc R U . . .
H11C H 0.009521 0.625810 0.497264 0.192 Uiso 1 1 calc R U . . .
C13 C 0.1543(10) 0.7977(8) 0.4501(16) 0.166(5) Uiso 1 1 d . . . . .
H13A H 0.232265 0.802434 0.437626 0.249 Uiso 1 1 calc R U . . .
H13B H 0.144941 0.822520 0.557590 0.249 Uiso 1 1 calc R U . . .
H13C H 0.106727 0.826759 0.356887 0.249 Uiso 1 1 calc R U . . .
O8 O 0.3687(3) 0.5775(3) 0.1644(5) 0.0630(9) Uani 1 1 d G . . . .
H8A H 0.329707 0.599231 0.233204 0.094 Uiso 1 1 d G U . . .
H8B H 0.332888 0.532644 0.127616 0.094 Uiso 1 1 d G 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 O1 2.074(2) . ?
Co1 O2 2.091(2) . ?
Co1 O3 2.098(2) . ?
Co1 O4 2.067(2) 3_566 ?
Co1 N1 2.170(3) . ?
Co1 N2 2.180(3) 3_666 ?
O1 C12 1.255(4) . ?
O2 H2A 0.8609 . ?
O2 H2B 0.8608 . ?
O3 H3A 0.8600 . ?
O3 H3B 0.8599 . ?
O4 C10 1.257(4) . ?
O5 C10 1.251(4) . ?
O6 C12 1.251(4) . ?
N1 C3 1.350(4) . ?
N1 C4 1.328(4) . ?
N2 C4 1.332(4) . ?
N2 C7 1.334(4) . ?
C1 C6 1.401(4) 3_565 ?
C1 C8 1.387(4) . ?
C1 C10 1.507(4) . ?
C2 H2 0.9400 . ?
C2 C3 1.373(5) . ?
C2 C7 1.380(5) . ?
C3 H3 0.9400 . ?
C4 C4 1.484(6) 3_666 ?
C6 C8 1.390(4) . ?
C6 C12 1.514(4) . ?
C7 H7 0.9400 . ?
C8 H8 0.9400 . ?
O7 C9 1.252(8) . ?
N3 C9 1.475(9) . ?
N3 C11 1.433(8) . ?
N3 C13 1.481(14) . ?
C9 H9 0.9400 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
O8 H8A 0.8600 . ?
O8 H8B 0.8597 . ?

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 O2 91.58(9) . . ?
O1 Co1 O3 177.93(9) . . ?
O1 Co1 N1 88.68(9) . . ?
O1 Co1 N2 91.89(9) . 3_666 ?
O2 Co1 O3 89.54(9) . . ?
O2 Co1 N1 90.26(9) . . ?
O2 Co1 N2 165.82(9) . 3_666 ?
O3 Co1 N1 93.06(9) . . ?
O3 Co1 N2 87.44(9) . 3_666 ?
O4 Co1 O1 88.22(9) 3_566 . ?
O4 Co1 O2 96.89(10) 3_566 . ?
O4 Co1 O3 89.91(9) 3_566 . ?
O4 Co1 N1 172.28(10) 3_566 . ?
O4 Co1 N2 96.96(10) 3_566 3_666 ?
N1 Co1 N2 76.08(9) . 3_666 ?
C12 O1 Co1 129.2(2) . . ?
Co1 O2 H2A 109.4 . . ?
Co1 O2 H2B 109.4 . . ?
H2A O2 H2B 104.4 . . ?
Co1 O3 H3A 109.3 . . ?
Co1 O3 H3B 109.4 . . ?
H3A O3 H3B 104.5 . . ?
C10 O4 Co1 130.1(2) . 3_566 ?
C3 N1 Co1 128.3(2) . . ?
C4 N1 Co1 115.58(19) . . ?
C4 N1 C3 116.2(3) . . ?
C4 N2 Co1 114.89(19) . 3_666 ?
C4 N2 C7 116.5(3) . . ?
C7 N2 Co1 128.5(2) . 3_666 ?
C6 C1 C10 121.6(3) 3_565 . ?
C8 C1 C6 119.3(3) . 3_565 ?
C8 C1 C10 118.9(3) . . ?
C3 C2 H2 121.0 . . ?
C3 C2 C7 117.9(3) . . ?
C7 C2 H2 121.0 . . ?
N1 C3 C2 121.4(3) . . ?
N1 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
N1 C4 N2 126.6(3) . . ?
N1 C4 C4 116.6(3) . 3_666 ?
N2 C4 C4 116.9(3) . 3_666 ?
C1 C6 C12 123.3(3) 3_565 . ?
C8 C6 C1 118.6(3) . 3_565 ?
C8 C6 C12 118.0(3) . . ?
N2 C7 C2 121.4(3) . . ?
N2 C7 H7 119.3 . . ?
C2 C7 H7 119.3 . . ?
C1 C8 C6 122.1(3) . . ?
C1 C8 H8 119.0 . . ?
C6 C8 H8 119.0 . . ?
O4 C10 C1 116.8(3) . . ?
O5 C10 O4 125.2(3) . . ?
O5 C10 C1 117.9(3) . . ?
O1 C12 C6 115.9(3) . . ?
O6 C12 O1 125.8(3) . . ?
O6 C12 C6 118.1(3) . . ?
C9 N3 C13 120.7(7) . . ?
C11 N3 C9 118.6(6) . . ?
C11 N3 C13 119.9(7) . . ?
O7 C9 N3 109.4(7) . . ?
O7 C9 H9 125.3 . . ?
N3 C9 H9 125.3 . . ?
N3 C11 H11A 109.5 . . ?
N3 C11 H11B 109.5 . . ?
N3 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
H8A O8 H8B 104.5 . . ?

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
Co1 O1 C12 O6 2.7(5) . . . . ?
Co1 O1 C12 C6 177.33(19) . . . . ?
Co1 O4 C10 O5 6.5(5) 3_566 . . . ?
Co1 O4 C10 C1 -170.0(2) 3_566 . . . ?
Co1 N1 C3 C2 179.4(3) . . . . ?
Co1 N1 C4 N2 179.4(2) . . . . ?
Co1 N1 C4 C4 -0.7(4) . . . 3_666 ?
Co1 N2 C4 N1 179.3(2) 3_666 . . . ?
Co1 N2 C4 C4 -0.5(4) 3_666 . . 3_666 ?
Co1 N2 C7 C2 -178.0(3) 3_666 . . . ?
C1 C6 C8 C1 1.0(5) 3_565 . . . ?
C1 C6 C12 O1 120.9(3) 3_565 . . . ?
C1 C6 C12 O6 -64.0(4) 3_565 . . . ?
C3 N1 C4 N2 -1.3(5) . . . . ?
C3 N1 C4 C4 178.6(3) . . . 3_666 ?
C3 C2 C7 N2 -0.5(5) . . . . ?
C4 N1 C3 C2 0.1(5) . . . . ?
C4 N2 C7 C2 -0.5(5) . . . . ?
C6 C1 C8 C6 -1.0(5) 3_565 . . . ?
C6 C1 C10 O4 -158.9(3) 3_565 . . . ?
C6 C1 C10 O5 24.3(4) 3_565 . . . ?
C7 N2 C4 N1 1.5(5) . . . . ?
C7 N2 C4 C4 -178.4(3) . . . 3_666 ?
C7 C2 C3 N1 0.7(5) . . . . ?
C8 C1 C10 O4 25.1(4) . . . . ?
C8 C1 C10 O5 -151.7(3) . . . . ?
C8 C6 C12 O1 -62.9(4) . . . . ?
C8 C6 C12 O6 112.2(3) . . . . ?
C10 C1 C8 C6 175.1(3) . . . . ?
C12 C6 C8 C1 -175.4(3) . . . . ?
C11 N3 C9 O7 169.3(8) . . . . ?
C13 N3 C9 O7 -0.8(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
