# 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_20211206chhcono3h_0m
_database_code_depnum_ccdc_archive 'CCDC 2226213'
_audit_update_record             
;
2022-12-13 deposited with the CCDC.	2023-05-08 downloaded from the CCDC.
;
_audit_creation_date             2022-03-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6394)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H12 Co N6 O6'
_chemical_formula_sum            'C16 H12 Co N6 O6'
_chemical_formula_weight         443.25
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   14.7033(7)
_cell_length_b                   9.1448(4)
_cell_length_c                   15.3254(8)
_cell_angle_alpha                90
_cell_angle_beta                 119.853(2)
_cell_angle_gamma                90
_cell_volume                     1787.20(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8065
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.72
_shelx_estimated_absorpt_T_max   0.924
_shelx_estimated_absorpt_T_min   0.888
_exptl_absorpt_coefficient_mu    1.010
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1009 before and 0.0427 after correction.
The Ratio of minimum to maximum transmission is 0.6576.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             900
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13966
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.672
_diffrn_reflns_theta_min         2.741
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1740
_reflns_number_total             2086
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.429
_refine_diff_density_min         -1.235
_refine_diff_density_rms         0.170
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.190
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         2086
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0480
_refine_ls_restrained_S_all      1.190
_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)+(0.0865P)²+1.6160P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1348
_refine_ls_wR_factor_ref         0.1632
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C6(H6), C7(H7), C8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.500000 0.30142(5) 0.250000 0.0593(3) Uani 1 2 d S T P . .
O1 O 0.49413(16) 0.1267(2) 0.14820(18) 0.0645(6) Uani 1 1 d . . . . .
O2 O 0.64325(17) 0.2062(2) 0.26051(17) 0.0609(5) Uani 1 1 d . . . . .
O3 O 0.63507(18) 0.0397(2) 0.15605(19) 0.0714(6) Uani 1 1 d . . . . .
N1 N 0.47942(19) 0.4738(3) 0.33106(16) 0.0528(5) Uani 1 1 d . . . . .
N2 N 0.6526(2) 0.4190(3) 0.4235(2) 0.0611(6) Uani 1 1 d . . . . .
N3 N 0.59264(17) 0.1207(2) 0.18794(17) 0.0503(5) Uani 1 1 d . . . . .
C1 C 0.3982(2) 0.5562(3) 0.3116(2) 0.0590(7) Uani 1 1 d . . . . .
H1 H 0.332842 0.529975 0.258572 0.071 Uiso 1 1 calc R U . . .
C2 C 0.4057(2) 0.6823(3) 0.3674(2) 0.0605(7) Uani 1 1 d . . . . .
H2 H 0.346586 0.739086 0.350081 0.073 Uiso 1 1 calc R U . . .
C3 C 0.4997(2) 0.7204(3) 0.4466(2) 0.0557(7) Uani 1 1 d . . . . .
H3 H 0.506047 0.803817 0.483964 0.067 Uiso 1 1 calc R U . . .
C4 C 0.58787(19) 0.6313(3) 0.47174(17) 0.0438(5) Uani 1 1 d . . . . .
C5 C 0.5738(2) 0.5098(3) 0.41068(17) 0.0452(5) Uani 1 1 d . . . . .
C6 C 0.7459(2) 0.4459(3) 0.4993(3) 0.0637(7) Uani 1 1 d . . . . .
H6 H 0.800798 0.385254 0.508716 0.076 Uiso 1 1 calc R U . . .
C7 C 0.7676(2) 0.5601(3) 0.5668(2) 0.0612(7) Uani 1 1 d . . . . .
H7 H 0.835118 0.572556 0.620833 0.073 Uiso 1 1 calc R U . . .
C8 C 0.6898(2) 0.6535(3) 0.5534(2) 0.0519(6) Uani 1 1 d . . . . .
H8 H 0.703584 0.731026 0.597525 0.062 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 O1 2.205(2) . ?
Co1 O1 2.205(2) 2_655 ?
Co1 O2 2.210(2) 2_655 ?
Co1 O2 2.210(2) . ?
Co1 N1 2.120(2) 2_655 ?
Co1 N1 2.120(2) . ?
O1 N3 1.262(3) . ?
O2 N3 1.256(3) . ?
O3 N3 1.217(3) . ?
N1 C1 1.315(4) . ?
N1 C5 1.356(3) . ?
N2 C5 1.358(4) . ?
N2 C6 1.306(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.407(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.354(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.413(4) . ?
C4 C5 1.400(3) . ?
C4 C8 1.409(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.391(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.359(4) . ?
C8 H8 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 87.11(12) . 2_655 ?
O1 Co1 O2 57.74(8) 2_655 2_655 ?
O1 Co1 O2 57.74(8) . . ?
O1 Co1 O2 87.87(8) 2_655 . ?
O1 Co1 O2 87.86(8) . 2_655 ?
O2 Co1 O2 133.59(11) 2_655 . ?
N1 Co1 O1 95.22(9) 2_655 . ?
N1 Co1 O1 95.22(9) . 2_655 ?
N1 Co1 O1 170.71(8) . . ?
N1 Co1 O1 170.71(8) 2_655 2_655 ?
N1 Co1 O2 131.24(8) 2_655 2_655 ?
N1 Co1 O2 131.24(8) . . ?
N1 Co1 O2 85.80(9) . 2_655 ?
N1 Co1 O2 85.80(8) 2_655 . ?
N1 Co1 N1 83.92(12) 2_655 . ?
N3 O1 Co1 93.37(16) . . ?
N3 O2 Co1 93.31(15) . . ?
C1 N1 Co1 132.23(19) . . ?
C1 N1 C5 118.2(2) . . ?
C5 N1 Co1 109.10(18) . . ?
C6 N2 C5 117.1(2) . . ?
O2 N3 O1 115.6(2) . . ?
O3 N3 O1 121.8(2) . . ?
O3 N3 O2 122.6(2) . . ?
N1 C1 H1 118.5 . . ?
N1 C1 C2 123.0(3) . . ?
C2 C1 H1 118.5 . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.4(3) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 120.5 . . ?
C2 C3 C4 119.0(3) . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 117.7(2) . . ?
C5 C4 C8 116.5(2) . . ?
C8 C4 C3 125.8(2) . . ?
N1 C5 N2 113.5(2) . . ?
N1 C5 C4 122.6(2) . . ?
N2 C5 C4 123.9(2) . . ?
N2 C6 H6 118.2 . . ?
N2 C6 C7 123.7(3) . . ?
C7 C6 H6 118.2 . . ?
C6 C7 H7 120.2 . . ?
C8 C7 C6 119.6(3) . . ?
C8 C7 H7 120.2 . . ?
C4 C8 H8 120.4 . . ?
C7 C8 C4 119.1(3) . . ?
C7 C8 H8 120.4 . . ?

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 N3 O2 1.0(2) . . . . ?
Co1 O1 N3 O3 -177.3(2) . . . . ?
Co1 O2 N3 O1 -1.0(2) . . . . ?
Co1 O2 N3 O3 177.2(2) . . . . ?
Co1 N1 C1 C2 -168.6(2) . . . . ?
Co1 N1 C5 N2 -6.4(3) . . . . ?
Co1 N1 C5 C4 172.26(18) . . . . ?
N1 C1 C2 C3 -1.7(5) . . . . ?
N2 C6 C7 C8 -2.0(5) . . . . ?
C1 N1 C5 N2 -179.2(2) . . . . ?
C1 N1 C5 C4 -0.6(4) . . . . ?
C1 C2 C3 C4 -0.5(5) . . . . ?
C2 C3 C4 C5 2.0(4) . . . . ?
C2 C3 C4 C8 -178.0(3) . . . . ?
C3 C4 C5 N1 -1.5(4) . . . . ?
C3 C4 C5 N2 177.0(2) . . . . ?
C3 C4 C8 C7 -178.5(3) . . . . ?
C5 N1 C1 C2 2.3(4) . . . . ?
C5 N2 C6 C7 0.6(4) . . . . ?
C5 C4 C8 C7 1.5(4) . . . . ?
C6 N2 C5 N1 -179.4(2) . . . . ?
C6 N2 C5 C4 2.0(4) . . . . ?
C6 C7 C8 C4 0.8(4) . . . . ?
C8 C4 C5 N1 178.5(2) . . . . ?
C8 C4 C5 N2 -3.0(4) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.248 0.070 0.247 15.0 1.7 ?
2 0.252 0.430 0.753 15.0 1.8 ?
3 0.748 0.570 0.247 15.0 1.7 ?
4 0.752 -0.070 0.753 15.0 1.8 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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_1
_database_code_depnum_ccdc_archive 'CCDC 2226214'
_audit_update_record             
;
2022-12-13 deposited with the CCDC.	2023-05-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H12 Co N6 O6'
_chemical_formula_sum            'C16 H12 Co N6 O6'
_chemical_formula_weight         443.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   14.509(3)
_cell_length_b                   9.1423(18)
_cell_length_c                   14.924(3)
_cell_angle_alpha                90
_cell_angle_beta                 119.08
_cell_angle_gamma                90
_cell_volume                     1729.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    155(2)
_cell_measurement_reflns_used    5766
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      25.17

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_F_000             900
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    1.044
_shelx_estimated_absorpt_T_min   0.759
_shelx_estimated_absorpt_T_max   0.826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5488
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      155(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12477
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.606
_diffrn_reflns_theta_max         25.265
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             3078
_reflns_number_gt                2783
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0319P)²+0.7523P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3078
_refine_ls_number_parameters     262
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0249
_refine_ls_wR_factor_ref         0.0679
_refine_ls_wR_factor_gt          0.0650
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_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
C1 C 0.63392(13) 0.68447(19) 0.81399(13) 0.0200(4) Uani 1 1 d . . . . .
H1 H 0.5655 0.7089 0.7604 0.024 Uiso 1 1 calc R U . . .
C2 C 0.64612(14) 0.55891(19) 0.87338(14) 0.0212(4) Uani 1 1 d . . . . .
H2 H 0.5869 0.4991 0.8587 0.025 Uiso 1 1 calc R U . . .
C3 C 0.74355(14) 0.52317(19) 0.95234(14) 0.0202(4) Uani 1 1 d . . . . .
H3 H 0.7525 0.4382 0.9924 0.024 Uiso 1 1 calc R U . . .
C4 C 0.83078(13) 0.61432(18) 0.97366(12) 0.0167(4) Uani 1 1 d . . . . .
C5 C 0.81093(13) 0.73422(18) 0.90844(12) 0.0166(4) Uani 1 1 d . . . . .
C6 C 0.98400(14) 0.80594(19) 0.98764(13) 0.0210(4) Uani 1 1 d . . . . .
H6 H 1.0379 0.8694 0.9921 0.025 Uiso 1 1 calc R U . . .
C7 C 1.01162(14) 0.69252(19) 1.05967(13) 0.0206(4) Uani 1 1 d . . . . .
H7 H 1.0825 0.6827 1.1130 0.025 Uiso 1 1 calc R U . . .
C8 C 0.93669(13) 0.59650(19) 1.05308(13) 0.0192(4) Uani 1 1 d . . . . .
H8 H 0.9550 0.5187 1.1009 0.023 Uiso 1 1 calc R U . . .
C9 C 0.84355(13) 0.70127(19) 0.69080(13) 0.0193(4) Uani 1 1 d . . . . .
H9 H 0.9103 0.7307 0.7451 0.023 Uiso 1 1 calc R U . . .
C10 C 0.83785(14) 0.57065(19) 0.63957(14) 0.0211(4) Uani 1 1 d . . . . .
H10 H 0.8989 0.5118 0.6605 0.025 Uiso 1 1 calc R U . . .
C11 C 0.74337(14) 0.52871(19) 0.55904(14) 0.0200(4) Uani 1 1 d . . . . .
H11 H 0.7376 0.4393 0.5242 0.024 Uiso 1 1 calc R U . . .
C12 C 0.65428(13) 0.62021(18) 0.52816(12) 0.0163(4) Uani 1 1 d . . . . .
C13 C 0.66559(12) 0.74734(18) 0.58608(12) 0.0156(3) Uani 1 1 d . . . . .
C14 C 0.49213(13) 0.80833(18) 0.48724(13) 0.0198(4) Uani 1 1 d . . . . .
H14 H 0.4347 0.8718 0.4729 0.024 Uiso 1 1 calc R U . . .
C15 C 0.47286(13) 0.68708(19) 0.42224(13) 0.0201(4) Uani 1 1 d . . . . .
H15 H 0.4050 0.6717 0.3649 0.024 Uiso 1 1 calc R U . . .
C16 C 0.55327(14) 0.59225(19) 0.44298(13) 0.0192(4) Uani 1 1 d . . . . .
H16 H 0.5419 0.5086 0.4011 0.023 Uiso 1 1 calc R U . . .
Co1 Co 0.76562(2) 0.95094(2) 0.76958(2) 0.01574(10) Uani 1 1 d . U . . .
N1 N 0.71395(11) 0.76932(15) 0.83010(11) 0.0184(3) Uani 1 1 d . . . . .
N2 N 0.88616(11) 0.82824(15) 0.91382(11) 0.0191(3) Uani 1 1 d . . . . .
N3 N 0.76087(11) 0.78652(15) 0.66780(10) 0.0165(3) Uani 1 1 d . . . . .
N4 N 0.58450(11) 0.83974(15) 0.56676(11) 0.0187(3) Uani 1 1 d . . . . .
N5 N 0.66899(11) 1.13303(15) 0.82559(11) 0.0179(3) Uani 1 1 d . U . . .
N6 N 0.85322(11) 1.13005(15) 0.69650(11) 0.0185(3) Uani 1 1 d . . . . .
O1 O 0.61863(9) 1.05026(12) 0.74895(9) 0.0194(3) Uani 1 1 d . U . . .
O2 O 0.76974(9) 1.12265(13) 0.87000(9) 0.0202(3) Uani 1 1 d . U . . .
O3 O 0.62505(10) 1.21601(13) 0.85703(10) 0.0242(3) Uani 1 1 d . . . . .
O4 O 0.90651(9) 1.03931(13) 0.76762(10) 0.0227(3) Uani 1 1 d . . . . .
O5 O 0.75477(9) 1.13142(13) 0.66438(9) 0.0220(3) Uani 1 1 d . U . . .
O6 O 0.89441(10) 1.21019(13) 0.66035(10) 0.0251(3) 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
C1 N1 1.318(2) . ?
C1 C2 1.408(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.369(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.416(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.400(2) . ?
C4 C8 1.422(2) . ?
C5 N1 1.360(2) . ?
C5 N2 1.361(2) . ?
C6 N2 1.323(2) . ?
C6 C7 1.405(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.363(2) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 N3 1.328(2) . ?
C9 C10 1.399(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.367(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.416(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.410(2) . ?
C12 C16 1.421(2) . ?
C13 N4 1.361(2) . ?
C13 N3 1.374(2) . ?
C14 N4 1.319(2) . ?
C14 C15 1.409(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.363(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
Co1 N3 2.1141(14) . ?
Co1 O2 2.1510(12) . ?
Co1 N1 2.1893(15) . ?
Co1 O1 2.1975(13) . ?
Co1 O4 2.2114(13) . ?
Co1 O5 2.2297(13) . ?
Co1 N2 2.3001(15) . ?
N5 O3 1.2219(18) . ?
N5 O1 1.2657(19) . ?
N5 O2 1.2819(18) . ?
N6 O6 1.2242(18) . ?
N6 O5 1.2667(18) . ?
N6 O4 1.2707(19) . ?

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
N1 C1 C2 122.35(16) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C3 C2 C1 119.86(16) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 119.27(16) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 116.44(16) . . ?
C5 C4 C8 116.30(16) . . ?
C3 C4 C8 127.26(16) . . ?
N1 C5 N2 111.51(15) . . ?
N1 C5 C4 124.03(16) . . ?
N2 C5 C4 124.45(15) . . ?
N2 C6 C7 122.86(16) . . ?
N2 C6 H6 118.6 . . ?
C7 C6 H6 118.6 . . ?
C8 C7 C6 119.96(16) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C4 119.16(16) . . ?
C7 C8 H8 120.4 . . ?
C4 C8 H8 120.4 . . ?
N3 C9 C10 123.63(16) . . ?
N3 C9 H9 118.2 . . ?
C10 C9 H9 118.2 . . ?
C11 C10 C9 119.18(16) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C12 119.16(16) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C13 C12 C11 118.16(15) . . ?
C13 C12 C16 117.33(15) . . ?
C11 C12 C16 124.51(16) . . ?
N4 C13 N3 114.81(15) . . ?
N4 C13 C12 123.44(15) . . ?
N3 C13 C12 121.75(15) . . ?
N4 C14 C15 124.43(16) . . ?
N4 C14 H14 117.8 . . ?
C15 C14 H14 117.8 . . ?
C16 C15 C14 118.87(16) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C15 C16 C12 119.05(16) . . ?
C15 C16 H16 120.5 . . ?
C12 C16 H16 120.5 . . ?
N3 Co1 O2 178.43(5) . . ?
N3 Co1 N1 81.90(6) . . ?
O2 Co1 N1 99.51(5) . . ?
N3 Co1 O1 120.18(5) . . ?
O2 Co1 O1 59.50(4) . . ?
N1 Co1 O1 82.39(5) . . ?
N3 Co1 O4 87.58(5) . . ?
O2 Co1 O4 91.71(5) . . ?
N1 Co1 O4 141.87(5) . . ?
O1 Co1 O4 133.44(5) . . ?
N3 Co1 O5 93.09(5) . . ?
O2 Co1 O5 85.36(5) . . ?
N1 Co1 O5 158.52(5) . . ?
O1 Co1 O5 82.19(4) . . ?
O4 Co1 O5 57.97(4) . . ?
N3 Co1 N2 94.01(5) . . ?
O2 Co1 N2 87.30(5) . . ?
N1 Co1 N2 60.07(5) . . ?
O1 Co1 N2 125.26(5) . . ?
O4 Co1 N2 84.45(5) . . ?
O5 Co1 N2 141.36(5) . . ?
C1 N1 C5 118.00(15) . . ?
C1 N1 Co1 145.01(12) . . ?
C5 N1 Co1 96.60(11) . . ?
C6 N2 C5 117.20(15) . . ?
C6 N2 Co1 150.99(12) . . ?
C5 N2 Co1 91.70(10) . . ?
C9 N3 C13 117.98(15) . . ?
C9 N3 Co1 121.44(11) . . ?
C13 N3 Co1 119.37(11) . . ?
C14 N4 C13 116.82(15) . . ?
O3 N5 O1 122.58(14) . . ?
O3 N5 O2 121.61(14) . . ?
O1 N5 O2 115.80(13) . . ?
O6 N6 O5 121.98(14) . . ?
O6 N6 O4 121.98(14) . . ?
O5 N6 O4 116.03(13) . . ?
N5 O1 Co1 91.48(9) . . ?
N5 O2 Co1 93.17(9) . . ?
N6 O4 Co1 93.35(9) . . ?
N6 O5 Co1 92.61(9) . . ?

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.083



