# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_TMC-2_333K
_database_code_depnum_ccdc_archive 'CCDC 2003376'
loop_
_audit_author_name
_audit_author_address
'Wei-Jian Xu'
;Sun Yat Sen university
China
;
_audit_update_record             
;
2020-05-11 deposited with the CCDC.	2020-07-17 downloaded from the CCDC.
;
_audit_creation_date             2020-04-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C12 H4 Co2 N12 Na2 O2), 2(C3 H11 N2)'
_chemical_formula_sum            'C12 H24 Co N10 Na O'
_chemical_formula_weight         406.33
_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'
Na Na 0.0362 0.0249 '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      orthorhombic
_space_group_IT_number           59
_space_group_name_H-M_alt        'P m m n'
_space_group_name_Hall           '-P 2ab 2a'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z'
'x+1/2, -y, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z'
'-x-1/2, y, z'

_cell_length_a                   8.4803(3)
_cell_length_b                   12.4172(9)
_cell_length_c                   9.5901(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1009.85(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2845
_cell_measurement_temperature    333(2)
_cell_measurement_theta_max      30.3020
_cell_measurement_theta_min      2.6750
_shelx_estimated_absorpt_T_max   1.671
_shelx_estimated_absorpt_T_min   0.638
_exptl_absorpt_coefficient_mu    0.893
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41404
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.38.40t (Rigaku Oxford Diffraction, 2015)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4491
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.968
_diffrn_reflns_theta_min         2.684
_diffrn_ambient_temperature      333(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                929
_reflns_number_total             1100
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         1100
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0494
_refine_ls_restrained_S_all      1.031
_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)+(0.1025P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1268
_refine_ls_wR_factor_ref         0.1346
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, All N(H,H) groups, All O(H,H) groups
2. Restrained distances
 N4-C4
 1.481 with sigma of 0.002
 C6-C4
 2.451 with sigma of 0.002
 C4-C5
 2.352 with sigma of 0.002
 C6-C5
 2.455 with sigma of 0.002
 C5-N4
 1.459 with sigma of 0.005
 N4-C6
 1.481 with sigma of 0.002
 N4-N5
 1.481 with sigma of 0.002
 N5-C4
 2.451 with sigma of 0.002
 C6-N5
 2.451 with sigma of 0.002
 C5-N5
 2.352 with sigma of 0.002
3. Others
 Fixed Sof: Na1(0.25) N4(0.5) C5(0.5) H5A(0.5) H5B(0.5) H5C(0.5) N5(0.5)
 H5D(0.5) H5E(0.5) C4(0.5) H4A(0.5) H4B(0.5) H4C(0.5) C6(0.5) H6A(0.5) H6B(0.5)
 H6C(0.5) O1(0.25) H1A(0.25) H1B(0.25)
4.a Riding coordinates:
 C5(H5A,H5B,H5C), N5(H5D,H5E), C4(H4A,H4B,H4C)
4.b Rotating group:
 O1(H1A,H1B)
4.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.7500 0.7500 0.70244(5) 0.0616(3) Uani 1 4 d S T P B .
Na1 Na 0.2500 0.6962(2) 0.3615(3) 0.0706(7) Uani 0.5 2 d S T P . .
N3 N 0.4859(4) 0.7500 0.4885(4) 0.1024(10) Uani 1 2 d S T P B .
C3 C 0.5875(4) 0.7500 0.5664(3) 0.0719(8) Uani 1 2 d S T P . .
C2 C 0.7500 0.5970(4) 0.6999(4) 0.0844(10) Uani 1 2 d S T P . .
C1 C 0.5943(5) 0.7500 0.8434(4) 0.0835(9) Uani 1 2 d S T P . .
N1 N 0.5026(5) 0.7500 0.9299(4) 0.1287(15) Uani 1 2 d S T P B .
N2 N 0.7500 0.5051(4) 0.6928(4) 0.1324(19) Uani 1 2 d S T P B .
N4 N 0.2551(10) 0.4776(3) 0.7831(3) 0.0859(13) Uani 0.5 1 d D . . A -1
C5 C 0.270(2) 0.5609(6) 0.6747(6) 0.237(9) Uani 0.5 1 d D . . A -1
H5A H 0.2050 0.6209 0.7000 0.356 Uiso 0.5 1 d R . . A -1
H5B H 0.3781 0.5842 0.6681 0.356 Uiso 0.5 1 d R . . A -1
H5C H 0.2368 0.5328 0.5863 0.356 Uiso 0.5 1 d R . . A -1
N5 N 0.3072(12) 0.5295(6) 0.9144(5) 0.215(6) Uani 0.5 1 d D . . A -1
H5D H 0.2979 0.4764 0.9867 0.323 Uiso 0.5 1 d R . . A -1
H5E H 0.4145 0.5537 0.9087 0.323 Uiso 0.5 1 d R . . A -1
C4 C 0.3651(12) 0.3905(7) 0.7408(13) 0.192(6) Uani 0.5 1 d D . . A -1
H4A H 0.4565 0.3893 0.7999 0.288 Uiso 0.5 1 d R . . A -1
H4B H 0.3103 0.3231 0.7482 0.288 Uiso 0.5 1 d R . . A -1
H4C H 0.3971 0.4017 0.6459 0.288 Uiso 0.5 1 d R . . A -1
C6 C 0.0912(11) 0.4367(9) 0.7951(13) 0.196(7) Uani 0.5 1 d D . . A -1
H6A H 0.0190 0.4908 0.7630 0.295 Uiso 0.5 1 calc GR . . A -1
H6B H 0.0689 0.4197 0.8907 0.295 Uiso 0.5 1 calc GR . . A -1
H6C H 0.0798 0.3730 0.7391 0.295 Uiso 0.5 1 calc GR . . A -1
O1 O 0.2376(18) 0.7674(12) 0.1451(8) 0.136(5) Uani 0.25 1 d . . . B -1
H1A H 0.1507 0.8398 0.1123 0.204 Uiso 0.25 1 d GR . . B -1
H1B H 0.3429 0.8120 0.0989 0.204 Uiso 0.25 1 d GR . . B -1


_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 C3 1.898(3) . ?
Co1 C3 1.898(3) 2_665 ?
Co1 C2 1.900(5) 2_665 ?
Co1 C2 1.900(5) . ?
Co1 C1 1.890(4) 2_665 ?
Co1 C1 1.890(4) . ?
Na1 Na1 1.337(5) 2_565 ?
Na1 N3 2.435(3) . ?
Na1 N3 2.435(3) 2_565 ?
Na1 N2 2.553(6) 5_666 ?
Na1 O1 2.259(6) . ?
N3 Na1 2.435(3) 2_565 ?
N3 C3 1.141(5) . ?
C2 N2 1.143(7) . ?
C1 N1 1.137(5) . ?
N2 Na1 2.553(6) 5_666 ?
N4 C5 1.473(3) . ?
N4 N5 1.4820(19) . ?
N4 C4 1.4844(19) . ?
N4 C6 1.4843(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
C3 Co1 C3 93.14(18) . 2_665 ?
C3 Co1 C2 89.49(7) . 2_665 ?
C3 Co1 C2 89.49(7) 2_665 2_665 ?
C3 Co1 C2 89.49(7) 2_665 . ?
C3 Co1 C2 89.49(7) . . ?
C2 Co1 C2 178.5(2) . 2_665 ?
C1 Co1 C3 89.12(17) 2_665 2_665 ?
C1 Co1 C3 177.74(13) . 2_665 ?
C1 Co1 C3 177.74(13) 2_665 . ?
C1 Co1 C3 89.12(17) . . ?
C1 Co1 C2 90.53(7) . . ?
C1 Co1 C2 90.53(7) 2_665 2_665 ?
C1 Co1 C2 90.53(7) . 2_665 ?
C1 Co1 C2 90.53(7) 2_665 . ?
C1 Co1 C1 88.6(2) . 2_665 ?
Na1 Na1 N3 74.07(7) 2_565 . ?
Na1 Na1 N3 74.07(7) 2_565 2_565 ?
Na1 Na1 N2 168.23(10) 2_565 5_666 ?
Na1 Na1 O1 67.0(4) 2_565 . ?
N3 Na1 N3 110.45(19) . 2_565 ?
N3 Na1 N2 111.76(9) 2_565 5_666 ?
N3 Na1 N2 111.76(9) . 5_666 ?
O1 Na1 N3 108.3(5) . 2_565 ?
O1 Na1 N3 113.0(4) . . ?
O1 Na1 N2 101.3(4) . 5_666 ?
Na1 N3 Na1 31.86(13) 2_565 . ?
C3 N3 Na1 161.47(17) . . ?
C3 N3 Na1 161.47(17) . 2_565 ?
N3 C3 Co1 177.5(3) . . ?
N2 C2 Co1 177.3(3) . . ?
N1 C1 Co1 178.9(4) . . ?
C2 N2 Na1 171.7(3) . 5_666 ?
C5 N4 N5 105.52(18) . . ?
C5 N4 C4 105.28(18) . . ?
C5 N4 C6 112.2(2) . . ?
N5 N4 C4 111.24(19) . . ?
N5 N4 C6 111.25(19) . . ?
C6 N4 C4 111.11(19) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N5 H5E N1 0.96 2.56 3.204(8) 124.8 .

_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_TMC-2_200K
_database_code_depnum_ccdc_archive 'CCDC 2003377'
loop_
_audit_author_name
_audit_author_address
'Wei-Jian Xu'
;Sun Yat Sen university
China
;
_audit_update_record             
;
2020-05-11 deposited with the CCDC.	2020-07-17 downloaded from the CCDC.
;
_audit_creation_date             2020-02-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H24 Co N10 Na O'
_chemical_formula_sum            'C12 H24 Co N10 Na O'
_chemical_formula_weight         406.33
_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'
Na Na 0.0362 0.0249 '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                   8.3357(2)
_cell_length_b                   12.4689(3)
_cell_length_c                   18.5938(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.564(2)
_cell_angle_gamma                90
_cell_volume                     1932.49(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14863
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      31.8170
_cell_measurement_theta_min      1.9600
_shelx_estimated_absorpt_T_max   1.245
_shelx_estimated_absorpt_T_min   0.816
_exptl_absorpt_coefficient_mu    0.933
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72286
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.38.40t (Rigaku Oxford Diffraction, 2015)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17630
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_min         1.967
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3523
_reflns_number_total             3798
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.997
_refine_diff_density_rms         0.105
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3798
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0276
_refine_ls_restrained_S_all      1.075
_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)+(0.0433P)²+0.6892P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0700
_refine_ls_wR_factor_ref         0.0751
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Rotating group:
 O1(H1A,H1B)
2.b Secondary CH2 refined with riding coordinates:
 N8(H8A,H8B), N10(H10A,H10B)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C8(H8C,H8D,H8E), C9(H9A,H9B,H9C),
 C10(H10C,H10D,H10E), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.78304(2) 0.75380(2) 0.37163(2) 0.01048(8) Uani 1 1 d . . . . .
Na1 Na 0.29694(6) 0.65802(4) 0.20184(3) 0.01751(13) Uani 1 1 d . . . . .
C1 C 0.81039(15) 0.90378(11) 0.35981(7) 0.0139(3) Uani 1 1 d . . . . .
N7 N 0.28849(13) 0.47753(11) 0.37090(6) 0.0177(3) Uani 1 1 d . . . . .
O1 O 0.24923(16) 0.77776(10) 0.11202(7) 0.0323(3) Uani 1 1 d . . . . .
H1A H 0.2384 0.8416 0.1294 0.048 Uiso 1 1 d GR . . . .
H1B H 0.1622 0.7609 0.0891 0.048 Uiso 1 1 d GR . . . .
N1 N 0.81862(15) 0.99514(10) 0.35239(7) 0.0212(3) Uani 1 1 d . . . . .
C4 C 0.75002(16) 0.60433(12) 0.38211(7) 0.0170(3) Uani 1 1 d . . . . .
C2 C 0.62009(16) 0.78507(11) 0.43842(7) 0.0156(3) Uani 1 1 d . . . . .
N4 N 0.72779(16) 0.51382(11) 0.38712(8) 0.0299(3) Uani 1 1 d . . . . .
C5 C 0.95420(16) 0.72623(11) 0.30729(7) 0.0152(3) Uani 1 1 d . . . . .
N5 N 1.06179(14) 0.70851(11) 0.27105(7) 0.0236(3) Uani 1 1 d . . . . .
N8 N 0.38230(14) 0.50528(10) 0.30770(6) 0.0210(3) Uani 1 1 d . . . . .
H8A H 0.3976 0.4440 0.2842 0.025 Uiso 1 1 calc R . . . .
H8B H 0.4782 0.5253 0.3244 0.025 Uiso 1 1 calc R . . . .
N2 N 0.52567(15) 0.80938(11) 0.48012(7) 0.0269(3) Uani 1 1 d . . . . .
N6 N 0.53075(16) 0.75663(10) 0.25210(8) 0.0218(3) Uani 1 1 d . . . . .
N10 N 0.55178(14) 0.54683(11) 0.11449(7) 0.0237(3) Uani 1 1 d . . . . .
H10A H 0.5081 0.4827 0.1069 0.028 Uiso 1 1 calc R . . . .
H10B H 0.5436 0.5804 0.0724 0.028 Uiso 1 1 calc R . . . .
N9 N 0.72256(13) 0.52135(10) 0.11814(7) 0.0184(3) Uani 1 1 d . . . . .
C6 C 0.62817(18) 0.75555(10) 0.29620(8) 0.0145(3) Uani 1 1 d . . . . .
N3 N 1.01689(18) 0.74594(10) 0.49808(8) 0.0276(3) Uani 1 1 d . . . . .
C3 C 0.93047(18) 0.74996(10) 0.44968(8) 0.0159(3) Uani 1 1 d . . . . .
C11 C 0.12878(18) 0.44013(15) 0.34420(10) 0.0311(4) Uani 1 1 d . . . . .
H11A H 0.0793 0.4957 0.3160 0.047 Uiso 1 1 calc GR . . . .
H11B H 0.0618 0.4233 0.3844 0.047 Uiso 1 1 calc GR . . . .
H11C H 0.1424 0.3773 0.3150 0.047 Uiso 1 1 calc GR . . . .
C12 C 0.36729(19) 0.39201(13) 0.41529(9) 0.0261(3) Uani 1 1 d . . . . .
H12A H 0.3875 0.3304 0.3858 0.039 Uiso 1 1 calc GR . . . .
H12B H 0.2980 0.3722 0.4540 0.039 Uiso 1 1 calc GR . . . .
H12C H 0.4669 0.4186 0.4346 0.039 Uiso 1 1 calc GR . . . .
C8 C 0.7851(2) 0.47630(15) 0.04945(10) 0.0347(4) Uani 1 1 d . . . . .
H8C H 0.7305 0.4104 0.0386 0.052 Uiso 1 1 calc GR . . . .
H8D H 0.8980 0.4628 0.0544 0.052 Uiso 1 1 calc GR . . . .
H8E H 0.7670 0.5267 0.0112 0.052 Uiso 1 1 calc GR . . . .
C9 C 0.80943(18) 0.62260(13) 0.13429(10) 0.0282(3) Uani 1 1 d . . . . .
H9A H 0.8012 0.6700 0.0937 0.042 Uiso 1 1 calc GR . . . .
H9B H 0.9203 0.6071 0.1440 0.042 Uiso 1 1 calc GR . . . .
H9C H 0.7629 0.6562 0.1756 0.042 Uiso 1 1 calc GR . . . .
C10 C 0.2719(2) 0.57733(14) 0.41419(9) 0.0340(4) Uani 1 1 d . . . . .
H10C H 0.3763 0.6025 0.4285 0.051 Uiso 1 1 calc GR . . . .
H10D H 0.2097 0.5625 0.4562 0.051 Uiso 1 1 calc GR . . . .
H10E H 0.2190 0.6313 0.3858 0.051 Uiso 1 1 calc GR . . . .
C7 C 0.7455(2) 0.44386(19) 0.17759(13) 0.0524(6) Uani 1 1 d . . . . .
H7A H 0.7084 0.4750 0.2216 0.079 Uiso 1 1 calc GR . . . .
H7B H 0.8573 0.4266 0.1823 0.079 Uiso 1 1 calc GR . . . .
H7C H 0.6857 0.3798 0.1674 0.079 Uiso 1 1 calc GR . . . .


_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 C1 1.8970(14) . ?
Co1 C4 1.8942(15) . ?
Co1 C2 1.8902(14) . ?
Co1 C5 1.9022(14) . ?
Co1 C6 1.8971(16) . ?
Co1 C3 1.8930(16) . ?
Na1 O1 2.2724(13) . ?
Na1 N1 2.4597(13) 2_645 ?
Na1 N5 2.4381(13) 1_455 ?
Na1 N8 2.8250(14) . ?
Na1 N6 2.4795(14) . ?
Na1 N10 3.0233(13) . ?
C1 N1 1.1496(19) . ?
N7 N8 1.4595(16) . ?
N7 C11 1.4911(18) . ?
N7 C12 1.4964(18) . ?
N7 C10 1.489(2) . ?
N1 Na1 2.4597(13) 2_655 ?
C4 N4 1.148(2) . ?
C2 N2 1.1508(19) . ?
C5 N5 1.1485(19) . ?
N5 Na1 2.4381(13) 1_655 ?
N6 C6 1.148(2) . ?
N10 N9 1.4595(16) . ?
N9 C8 1.494(2) . ?
N9 C9 1.4846(19) . ?
N9 C7 1.479(2) . ?
N3 C3 1.148(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Co1 C5 90.78(6) . . ?
C1 Co1 C6 89.12(5) . . ?
C4 Co1 C1 178.38(5) . . ?
C4 Co1 C5 89.86(6) . . ?
C4 Co1 C6 89.36(6) . . ?
C2 Co1 C1 87.75(6) . . ?
C2 Co1 C4 91.68(6) . . ?
C2 Co1 C5 177.19(6) . . ?
C2 Co1 C6 89.72(6) . . ?
C2 Co1 C3 88.10(6) . . ?
C6 Co1 C5 92.65(6) . . ?
C3 Co1 C1 92.06(5) . . ?
C3 Co1 C4 89.44(6) . . ?
C3 Co1 C5 89.56(6) . . ?
C3 Co1 C6 177.48(6) . . ?
O1 Na1 N1 100.15(5) . 2_645 ?
O1 Na1 N5 94.73(5) . 1_455 ?
O1 Na1 N8 174.97(5) . . ?
O1 Na1 N6 94.73(5) . . ?
O1 Na1 N10 91.45(5) . . ?
N1 Na1 N8 79.86(4) 2_645 . ?
N1 Na1 N6 150.13(5) 2_645 . ?
N1 Na1 N10 71.07(4) 2_645 . ?
N5 Na1 N1 96.66(5) 1_455 2_645 ?
N5 Na1 N8 90.26(4) 1_455 . ?
N5 Na1 N6 107.82(5) 1_455 . ?
N5 Na1 N10 167.10(5) 1_455 . ?
N8 Na1 N10 83.78(4) . . ?
N6 Na1 N8 83.11(4) . . ?
N6 Na1 N10 82.88(4) . . ?
N1 C1 Co1 176.51(12) . . ?
N8 N7 C11 106.84(11) . . ?
N8 N7 C12 112.17(11) . . ?
N8 N7 C10 106.89(12) . . ?
C11 N7 C12 110.26(12) . . ?
C10 N7 C11 110.73(13) . . ?
C10 N7 C12 109.87(12) . . ?
C1 N1 Na1 147.54(11) . 2_655 ?
N4 C4 Co1 178.47(14) . . ?
N2 C2 Co1 176.06(13) . . ?
N5 C5 Co1 176.94(12) . . ?
C5 N5 Na1 174.78(12) . 1_655 ?
N7 N8 Na1 125.98(8) . . ?
C6 N6 Na1 144.19(11) . . ?
N9 N10 Na1 139.91(9) . . ?
N10 N9 C8 112.99(11) . . ?
N10 N9 C9 107.33(11) . . ?
N10 N9 C7 107.20(12) . . ?
C9 N9 C8 108.61(12) . . ?
C7 N9 C8 110.47(15) . . ?
C7 N9 C9 110.18(15) . . ?
N6 C6 Co1 177.88(13) . . ?
N3 C3 Co1 178.09(14) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
