# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_Co9YEtO_0m
_database_code_depnum_ccdc_archive 'CCDC 1871823'
_audit_update_record             
;
2018-10-07 deposited with the CCDC.
2018-11-28 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         'C20 H22 Co N4 O2'
_chemical_formula_sum            'C20 H22 Co N4 O2'
_chemical_formula_weight         409.34

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   13.789(3)
_cell_length_b                   11.399(3)
_cell_length_c                   12.212(3)
_cell_angle_alpha                90
_cell_angle_beta                 116.361(4)
_cell_angle_gamma                90
_cell_volume                     1720.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    1170
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      27.01

_exptl_crystal_description       platelet
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_F_000             852
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.023
_shelx_estimated_absorpt_T_min   0.749
_shelx_estimated_absorpt_T_max   0.822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.749
_exptl_absorpt_correction_T_max  0.822
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5566
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.431
_diffrn_reflns_theta_max         28.546
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2101
_reflns_number_gt                1772
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2101
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1231
_refine_ls_wR_factor_gt          0.1127
_refine_ls_goodness_of_fit_ref   0.879
_refine_ls_restrained_S_all      0.879
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.5000 0.42213(4) 0.7500 0.00997(16) Uani 1 2 d S T P . .
O1 O 0.62433(13) 0.52005(14) 0.78995(15) 0.0131(4) Uani 1 1 d . . . . .
C1 C 0.68978(19) 0.51109(19) 0.7384(2) 0.0114(5) Uani 1 1 d . . . . .
C2 C 0.7829(2) 0.58314(19) 0.7855(2) 0.0135(5) Uani 1 1 d . . . . .
H2 H 0.7927 0.6368 0.8491 0.016 Uiso 1 1 calc R U . . .
C3 C 0.8598(2) 0.57861(19) 0.7427(2) 0.0141(5) Uani 1 1 d . . . . .
H3 H 0.9206 0.6295 0.7755 0.017 Uiso 1 1 calc R U . . .
C4 C 0.84825(19) 0.4993(2) 0.6512(2) 0.0149(5) Uani 1 1 d . . . . .
H4 H 0.9026 0.4927 0.6238 0.018 Uiso 1 1 calc R U . . .
C5 C 0.7575(2) 0.43075(19) 0.6012(2) 0.0131(5) Uani 1 1 d . . . . .
H5 H 0.7503 0.3769 0.5387 0.016 Uiso 1 1 calc R U . . .
C6 C 0.67390(19) 0.43620(19) 0.6382(2) 0.0106(4) Uani 1 1 d . . . . .
C7 C 0.57350(19) 0.36802(19) 0.5665(2) 0.0107(4) Uani 1 1 d . . . . .
N1 N 0.55872(17) 0.33127(17) 0.45472(18) 0.0145(4) Uani 1 1 d . . . . .
H1N H 0.593(2) 0.368(2) 0.427(3) 0.012(7) Uiso 1 1 d . . . . .
C8 C 0.4760(2) 0.2481(2) 0.3787(2) 0.0136(5) Uani 1 1 d . . . . .
H8 H 0.5088 0.1880 0.3469 0.016 Uiso 1 1 calc R U . . .
H8A H 0.4193 0.2896 0.3082 0.016 Uiso 1 1 calc R U . . .
C9 C 0.4259(2) 0.1893(2) 0.4522(2) 0.0152(5) Uani 1 1 d . . . . .
H9 H 0.4760 0.1295 0.5071 0.018 Uiso 1 1 calc R U . . .
H9A H 0.3577 0.1497 0.3967 0.018 Uiso 1 1 calc R U . . .
C10 C 0.40304(19) 0.2823(2) 0.5268(2) 0.0131(5) Uani 1 1 d . . . . .
H10 H 0.3503 0.3396 0.4710 0.016 Uiso 1 1 calc R U . . .
H10A H 0.3706 0.2449 0.5758 0.016 Uiso 1 1 calc R U . . .
N2 N 0.50328(16) 0.34426(16) 0.60905(17) 0.0109(4) 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 1.9184(17) . ?
Co1 O1 1.9184(17) 2_656 ?
Co1 N2 1.9551(19) . ?
Co1 N2 1.9552(19) 2_656 ?
O1 C1 1.314(3) . ?
C1 C2 1.413(3) . ?
C1 C6 1.427(3) . ?
C2 C3 1.376(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.367(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.414(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.487(3) . ?
C7 N2 1.315(3) . ?
C7 N1 1.354(3) . ?
N1 C8 1.457(3) . ?
N1 H1N 0.81(3) . ?
C8 C9 1.511(3) . ?
C8 H8 0.9900 . ?
C8 H8A 0.9900 . ?
C9 C10 1.519(3) . ?
C9 H9 0.9900 . ?
C9 H9A 0.9900 . ?
C10 N2 1.478(3) . ?
C10 H10 0.9900 . ?
C10 H10A 0.9900 . ?

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 108.84(10) . 2_656 ?
O1 Co1 N2 96.93(7) . . ?
O1 Co1 N2 114.06(8) 2_656 . ?
O1 Co1 N2 114.06(8) . 2_656 ?
O1 Co1 N2 96.93(7) 2_656 2_656 ?
N2 Co1 N2 125.99(11) . 2_656 ?
C1 O1 Co1 124.01(15) . . ?
O1 C1 C2 116.9(2) . . ?
O1 C1 C6 125.5(2) . . ?
C2 C1 C6 117.5(2) . . ?
C3 C2 C1 122.5(2) . . ?
C3 C2 H2 118.7 . . ?
C1 C2 H2 118.7 . . ?
C2 C3 C4 119.8(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 119.1(2) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 123.1(2) . . ?
C4 C5 H5 118.4 . . ?
C6 C5 H5 118.4 . . ?
C5 C6 C1 117.6(2) . . ?
C5 C6 C7 117.9(2) . . ?
C1 C6 C7 124.5(2) . . ?
N2 C7 N1 121.8(2) . . ?
N2 C7 C6 122.1(2) . . ?
N1 C7 C6 116.1(2) . . ?
C7 N1 C8 124.7(2) . . ?
C7 N1 H1N 114(2) . . ?
C8 N1 H1N 120(2) . . ?
N1 C8 C9 110.22(19) . . ?
N1 C8 H8 109.6 . . ?
C9 C8 H8 109.6 . . ?
N1 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
H8 C8 H8A 108.1 . . ?
C8 C9 C10 108.53(18) . . ?
C8 C9 H9 110.0 . . ?
C10 C9 H9 110.0 . . ?
C8 C9 H9A 110.0 . . ?
C10 C9 H9A 110.0 . . ?
H9 C9 H9A 108.4 . . ?
N2 C10 C9 111.15(19) . . ?
N2 C10 H10 109.4 . . ?
C9 C10 H10 109.4 . . ?
N2 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
H10 C10 H10A 108.0 . . ?
C7 N2 C10 117.40(19) . . ?
C7 N2 Co1 124.31(16) . . ?
C10 N2 Co1 115.79(14) . . ?

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 C1 C2 -174.73(14) . . . . ?
Co1 O1 C1 C6 6.2(3) . . . . ?
O1 C1 C2 C3 177.4(2) . . . . ?
C6 C1 C2 C3 -3.5(3) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
C2 C3 C4 C5 3.1(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C1 -4.6(3) . . . . ?
C4 C5 C6 C7 172.6(2) . . . . ?
O1 C1 C6 C5 -174.7(2) . . . . ?
C2 C1 C6 C5 6.2(3) . . . . ?
O1 C1 C6 C7 8.2(4) . . . . ?
C2 C1 C6 C7 -170.8(2) . . . . ?
C5 C6 C7 N2 163.2(2) . . . . ?
C1 C6 C7 N2 -19.8(3) . . . . ?
C5 C6 C7 N1 -16.5(3) . . . . ?
C1 C6 C7 N1 160.5(2) . . . . ?
N2 C7 N1 C8 -10.2(4) . . . . ?
C6 C7 N1 C8 169.5(2) . . . . ?
C7 N1 C8 C9 -12.3(3) . . . . ?
N1 C8 C9 C10 44.5(3) . . . . ?
C8 C9 C10 N2 -58.7(2) . . . . ?
N1 C7 N2 C10 -4.0(3) . . . . ?
C6 C7 N2 C10 176.25(19) . . . . ?
N1 C7 N2 Co1 -165.32(16) . . . . ?
C6 C7 N2 Co1 15.0(3) . . . . ?
C9 C10 N2 C7 38.9(3) . . . . ?
C9 C10 N2 Co1 -158.23(15) . . . . ?

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
N1 H1N O1 0.81(3) 2.29(3) 3.059(3) 158(3) 6_565

_refine_diff_density_max         0.522
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.093

####################################################################### 
# 
# 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_0302161m_0m
_database_code_depnum_ccdc_archive 'CCDC 1871825'
_audit_update_record             
;
2018-10-07 deposited with the CCDC.
2018-11-28 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         'C18 H14 Co N4 O2, (C H4 O)'
_chemical_formula_sum            'C19 H18 Co N4 O3'
_chemical_formula_weight         409.30

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   9.6795(11)
_cell_length_b                   14.4187(16)
_cell_length_c                   25.494(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3558.1(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    4677
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      27.45

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_F_000             1688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.993
_shelx_estimated_absorpt_T_min   0.716
_shelx_estimated_absorpt_T_max   0.890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.716
_exptl_absorpt_correction_T_max  0.890
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22177
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.642
_diffrn_reflns_theta_max         28.490
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4417
_reflns_number_gt                3600
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0509P)²+1.3669P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4417
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0946
_refine_ls_wR_factor_gt          0.0905
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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
Co1 Co 0.35864(2) 0.51660(2) 0.62663(2) 0.01498(9) Uani 1 1 d . . . . .
O1 O 0.24899(13) 0.40559(9) 0.62369(5) 0.0195(3) Uani 1 1 d . . . . .
C1 C 0.13950(17) 0.38331(13) 0.65247(7) 0.0159(4) Uani 1 1 d . . . . .
C2 C 0.05427(19) 0.31114(13) 0.63444(7) 0.0186(4) Uani 1 1 d . . . . .
H2 H 0.0760 0.2811 0.6023 0.022 Uiso 1 1 calc R U . . .
C3 C -0.06032(19) 0.28306(13) 0.66243(7) 0.0205(4) Uani 1 1 d . . . . .
H3 H -0.1168 0.2345 0.6493 0.025 Uiso 1 1 calc R U . . .
C4 C -0.09386(19) 0.32533(13) 0.70982(8) 0.0205(4) Uani 1 1 d . . . . .
H4 H -0.1722 0.3055 0.7293 0.025 Uiso 1 1 calc R U . . .
C5 C -0.01155(19) 0.39664(13) 0.72820(7) 0.0184(4) Uani 1 1 d . . . . .
H5 H -0.0343 0.4255 0.7606 0.022 Uiso 1 1 calc R U . . .
C6 C 0.10480(18) 0.42754(12) 0.70030(7) 0.0148(3) Uani 1 1 d . . . . .
C7 C 0.18751(18) 0.50392(12) 0.72138(7) 0.0141(3) Uani 1 1 d . . . . .
N1 N 0.17875(16) 0.53562(11) 0.77107(6) 0.0164(3) Uani 1 1 d . . . . .
H1 H 0.129(2) 0.5134(15) 0.7963(11) 0.025(6) Uiso 1 1 d . . . . .
C8 C 0.26984(19) 0.60810(13) 0.77676(7) 0.0187(4) Uani 1 1 d . . . . .
H8 H 0.2859 0.6433 0.8077 0.022 Uiso 1 1 calc R U . . .
C9 C 0.33216(19) 0.61955(13) 0.72973(7) 0.0184(4) Uani 1 1 d . . . . .
H9 H 0.4000 0.6650 0.7218 0.022 Uiso 1 1 calc R U . . .
N2 N 0.28112(15) 0.55438(10) 0.69515(6) 0.0155(3) Uani 1 1 d . . . . .
O2 O 0.55681(13) 0.50508(9) 0.63236(5) 0.0170(3) Uani 1 1 d . . . . .
C10 C 0.65073(17) 0.52853(12) 0.59625(7) 0.0143(3) Uani 1 1 d . . . . .
C11 C 0.78913(19) 0.50266(13) 0.60528(7) 0.0177(4) Uani 1 1 d . . . . .
H11 H 0.8108 0.4678 0.6358 0.021 Uiso 1 1 calc R U . . .
C12 C 0.89392(19) 0.52622(13) 0.57130(8) 0.0189(4) Uani 1 1 d . . . . .
H12 H 0.9863 0.5084 0.5788 0.023 Uiso 1 1 calc R U . . .
C13 C 0.86426(19) 0.57629(13) 0.52592(7) 0.0194(4) Uani 1 1 d . . . . .
H13 H 0.9361 0.5935 0.5025 0.023 Uiso 1 1 calc R U . . .
C14 C 0.72968(18) 0.60055(12) 0.51550(7) 0.0160(4) Uani 1 1 d . . . . .
H14 H 0.7098 0.6333 0.4841 0.019 Uiso 1 1 calc R U . . .
C15 C 0.62033(17) 0.57858(12) 0.54969(7) 0.0136(3) Uani 1 1 d . . . . .
C16 C 0.48051(18) 0.60685(12) 0.53541(7) 0.0140(3) Uani 1 1 d . . . . .
N3 N 0.44783(16) 0.65373(11) 0.49111(6) 0.0167(3) Uani 1 1 d . . . . .
C17 C 0.30745(19) 0.66703(13) 0.48990(8) 0.0199(4) Uani 1 1 d . . . . .
H17 H 0.2561 0.6974 0.4632 0.024 Uiso 1 1 calc R U . . .
C18 C 0.25675(19) 0.62842(13) 0.53411(7) 0.0191(4) Uani 1 1 d . . . . .
H18 H 0.1622 0.6271 0.5441 0.023 Uiso 1 1 calc R U . . .
N4 N 0.36452(15) 0.59110(11) 0.56252(6) 0.0160(3) Uani 1 1 d . . . . .
O3 O 0.42458(14) 0.27342(10) 0.59613(5) 0.0222(3) Uani 1 1 d . . . . .
H3M H 0.3649 0.3114 0.6067 0.033 Uiso 1 1 calc R U . . .
C19 C 0.5204(3) 0.25540(18) 0.63699(9) 0.0376(6) Uani 1 1 d . . . . .
H19 H 0.5656 0.3134 0.6473 0.056 Uiso 1 1 calc R U . . .
H19A H 0.5901 0.2112 0.6246 0.056 Uiso 1 1 calc R U . . .
H19B H 0.4716 0.2291 0.6672 0.056 Uiso 1 1 calc R U . . .
H3A H 0.501(2) 0.6751(16) 0.4683(10) 0.031(6) Uiso 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 1.9220(13) . ?
Co1 O2 1.9309(13) . ?
Co1 N4 1.9566(16) . ?
Co1 N2 1.9776(15) . ?
O1 C1 1.328(2) . ?
C1 C2 1.405(3) . ?
C1 C6 1.417(3) . ?
C2 C3 1.380(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.405(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.464(3) . ?
C7 N2 1.341(2) . ?
C7 N1 1.349(2) . ?
N1 C8 1.375(2) . ?
N1 H1 0.86(3) . ?
C8 C9 1.352(3) . ?
C8 H8 0.9500 . ?
C9 N2 1.380(2) . ?
C9 H9 0.9500 . ?
O2 C10 1.337(2) . ?
C10 C11 1.410(2) . ?
C10 C15 1.420(2) . ?
C11 C12 1.377(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.393(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.375(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.407(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.460(2) . ?
C16 N4 1.338(2) . ?
C16 N3 1.354(2) . ?
N3 C17 1.373(2) . ?
N3 H3A 0.83(3) . ?
C17 C18 1.349(3) . ?
C17 H17 0.9500 . ?
C18 N4 1.379(2) . ?
C18 H18 0.9500 . ?
O3 C19 1.419(2) . ?
O3 H3M 0.8400 . ?
C19 H19 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?

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 118.68(6) . . ?
O1 Co1 N4 116.15(6) . . ?
O2 Co1 N4 94.67(6) . . ?
O1 Co1 N2 93.11(6) . . ?
O2 Co1 N2 109.50(6) . . ?
N4 Co1 N2 126.70(6) . . ?
C1 O1 Co1 128.34(12) . . ?
O1 C1 C2 117.82(16) . . ?
O1 C1 C6 123.76(16) . . ?
C2 C1 C6 118.42(16) . . ?
C3 C2 C1 121.33(17) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 120.54(17) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 119.05(17) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.75(18) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 118.90(17) . . ?
C5 C6 C7 119.43(16) . . ?
C1 C6 C7 121.67(16) . . ?
N2 C7 N1 109.09(15) . . ?
N2 C7 C6 126.50(16) . . ?
N1 C7 C6 124.41(16) . . ?
C7 N1 C8 108.43(15) . . ?
C7 N1 H1 127.4(16) . . ?
C8 N1 H1 124.0(16) . . ?
C9 C8 N1 106.58(16) . . ?
C9 C8 H8 126.7 . . ?
N1 C8 H8 126.7 . . ?
C8 C9 N2 108.88(16) . . ?
C8 C9 H9 125.6 . . ?
N2 C9 H9 125.6 . . ?
C7 N2 C9 107.02(15) . . ?
C7 N2 Co1 123.20(12) . . ?
C9 N2 Co1 128.02(12) . . ?
C10 O2 Co1 126.98(11) . . ?
O2 C10 C11 117.82(16) . . ?
O2 C10 C15 124.27(15) . . ?
C11 C10 C15 117.90(16) . . ?
C12 C11 C10 122.15(18) . . ?
C12 C11 H11 118.9 . . ?
C10 C11 H11 118.9 . . ?
C11 C12 C13 119.91(17) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 119.18(17) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C15 122.39(16) . . ?
C13 C14 H14 118.8 . . ?
C15 C14 H14 118.8 . . ?
C14 C15 C10 118.44(15) . . ?
C14 C15 C16 118.69(16) . . ?
C10 C15 C16 122.86(15) . . ?
N4 C16 N3 108.64(15) . . ?
N4 C16 C15 127.01(16) . . ?
N3 C16 C15 124.35(16) . . ?
C16 N3 C17 108.65(15) . . ?
C16 N3 H3A 128.6(17) . . ?
C17 N3 H3A 122.6(16) . . ?
C18 C17 N3 106.47(16) . . ?
C18 C17 H17 126.8 . . ?
N3 C17 H17 126.8 . . ?
C17 C18 N4 108.94(16) . . ?
C17 C18 H18 125.5 . . ?
N4 C18 H18 125.5 . . ?
C16 N4 C18 107.29(15) . . ?
C16 N4 Co1 123.31(12) . . ?
C18 N4 Co1 129.11(12) . . ?
C19 O3 H3M 109.5 . . ?
O3 C19 H19 109.5 . . ?
O3 C19 H19A 109.5 . . ?
H19 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?

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 C1 C2 163.21(13) . . . . ?
Co1 O1 C1 C6 -17.3(2) . . . . ?
O1 C1 C2 C3 179.12(17) . . . . ?
C6 C1 C2 C3 -0.4(3) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C4 C5 C6 C1 -1.0(3) . . . . ?
C4 C5 C6 C7 179.42(17) . . . . ?
O1 C1 C6 C5 -178.35(17) . . . . ?
C2 C1 C6 C5 1.1(3) . . . . ?
O1 C1 C6 C7 1.3(3) . . . . ?
C2 C1 C6 C7 -179.30(16) . . . . ?
C5 C6 C7 N2 -164.41(17) . . . . ?
C1 C6 C7 N2 16.0(3) . . . . ?
C5 C6 C7 N1 14.4(3) . . . . ?
C1 C6 C7 N1 -165.19(17) . . . . ?
N2 C7 N1 C8 -0.3(2) . . . . ?
C6 C7 N1 C8 -179.27(16) . . . . ?
C7 N1 C8 C9 0.4(2) . . . . ?
N1 C8 C9 N2 -0.4(2) . . . . ?
N1 C7 N2 C9 0.0(2) . . . . ?
C6 C7 N2 C9 178.98(17) . . . . ?
N1 C7 N2 Co1 166.01(11) . . . . ?
C6 C7 N2 Co1 -15.0(2) . . . . ?
C8 C9 N2 C7 0.3(2) . . . . ?
C8 C9 N2 Co1 -164.84(13) . . . . ?
Co1 O2 C10 C11 -171.38(12) . . . . ?
Co1 O2 C10 C15 9.3(2) . . . . ?
O2 C10 C11 C12 -177.85(17) . . . . ?
C15 C10 C11 C12 1.5(3) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
C11 C12 C13 C14 -0.8(3) . . . . ?
C12 C13 C14 C15 1.6(3) . . . . ?
C13 C14 C15 C10 -0.8(3) . . . . ?
C13 C14 C15 C16 -179.83(17) . . . . ?
O2 C10 C15 C14 178.60(16) . . . . ?
C11 C10 C15 C14 -0.7(2) . . . . ?
O2 C10 C15 C16 -2.4(3) . . . . ?
C11 C10 C15 C16 178.26(16) . . . . ?
C14 C15 C16 N4 179.10(17) . . . . ?
C10 C15 C16 N4 0.1(3) . . . . ?
C14 C15 C16 N3 -0.3(3) . . . . ?
C10 C15 C16 N3 -179.30(17) . . . . ?
N4 C16 N3 C17 -0.7(2) . . . . ?
C15 C16 N3 C17 178.80(16) . . . . ?
C16 N3 C17 C18 0.6(2) . . . . ?
N3 C17 C18 N4 -0.2(2) . . . . ?
N3 C16 N4 C18 0.6(2) . . . . ?
C15 C16 N4 C18 -178.92(17) . . . . ?
N3 C16 N4 Co1 174.87(11) . . . . ?
C15 C16 N4 Co1 -4.6(2) . . . . ?
C17 C18 N4 C16 -0.2(2) . . . . ?
C17 C18 N4 Co1 -174.08(13) . . . . ?

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
N1 H1 O2 0.86(3) 1.95(3) 2.766(2) 156(2) 6_557
O3 H3M O1 0.84 1.81 2.6483(19) 171.7 .
N3 H3A O3 0.83(3) 1.94(3) 2.752(2) 164(2) 5_666

_refine_diff_density_max         0.676
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_Co201m_0m
_database_code_depnum_ccdc_archive 'CCDC 1871824'
_audit_update_record             
;
2018-10-07 deposited with the CCDC.
2018-11-28 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         'C18 H18 Co N4 O2'
_chemical_formula_sum            'C18 H18 Co N4 O2'
_chemical_formula_weight         381.29

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   11.9830(19)
_cell_length_b                   7.6704(13)
_cell_length_c                   18.692(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.227(2)
_cell_angle_gamma                90
_cell_volume                     1657.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    2090
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      26.78

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_F_000             788
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.055
_shelx_estimated_absorpt_T_min   0.648
_shelx_estimated_absorpt_T_max   0.817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.648
_exptl_absorpt_correction_T_max  0.817
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10425
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.329
_diffrn_reflns_theta_max         28.486
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3976
_reflns_number_gt                3155
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0513P)²+0.1025P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3976
_refine_ls_number_parameters     234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1006
_refine_ls_wR_factor_gt          0.0953
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
Co1 Co 0.26338(3) 0.57454(4) 0.52189(2) 0.01467(11) Uani 1 1 d . . . . .
O1 O 0.26782(13) 0.3484(2) 0.56888(9) 0.0169(3) Uani 1 1 d . . . . .
C1 C 0.20990(19) 0.2999(3) 0.61673(12) 0.0148(5) Uani 1 1 d . . . . .
C2 C 0.23711(19) 0.1370(3) 0.65209(13) 0.0179(5) Uani 1 1 d . . . . .
H2 H 0.2957 0.0678 0.6405 0.021 Uiso 1 1 calc R U . . .
C3 C 0.1817(2) 0.0746(3) 0.70294(13) 0.0196(5) Uani 1 1 d . . . . .
H3 H 0.2015 -0.0364 0.7252 0.024 Uiso 1 1 calc R U . . .
C4 C 0.0966(2) 0.1752(3) 0.72140(13) 0.0206(5) Uani 1 1 d . . . . .
H4 H 0.0593 0.1348 0.7573 0.025 Uiso 1 1 calc R U . . .
C5 C 0.0671(2) 0.3326(3) 0.68738(13) 0.0190(5) Uani 1 1 d . . . . .
H5 H 0.0084 0.3998 0.7000 0.023 Uiso 1 1 calc R U . . .
C6 C 0.12057(19) 0.3991(3) 0.63415(12) 0.0139(4) Uani 1 1 d . . . . .
C7 C 0.08105(19) 0.5657(3) 0.59876(12) 0.0138(4) Uani 1 1 d . . . . .
N1 N -0.01565(17) 0.6429(3) 0.60949(11) 0.0162(4) Uani 1 1 d . . . . .
H1 H -0.074(2) 0.584(3) 0.6116(15) 0.025(7) Uiso 1 1 d . . . . .
C8 C -0.0382(2) 0.8062(3) 0.56712(13) 0.0185(5) Uani 1 1 d . . . . .
H8 H -0.0365 0.9077 0.6001 0.022 Uiso 1 1 calc R U . . .
H8A H -0.1138 0.8027 0.5296 0.022 Uiso 1 1 calc R U . . .
C9 C 0.06268(19) 0.8124(3) 0.53037(13) 0.0160(5) Uani 1 1 d . . . . .
H9 H 0.0334 0.8097 0.4757 0.019 Uiso 1 1 calc R U . . .
H9A H 0.1091 0.9196 0.5449 0.019 Uiso 1 1 calc R U . . .
N2 N 0.13254(16) 0.6563(2) 0.55742(10) 0.0144(4) Uani 1 1 d . . . . .
O2 O 0.22631(13) 0.5471(2) 0.41530(9) 0.0175(3) Uani 1 1 d . . . . .
C10 C 0.29312(19) 0.5869(3) 0.37147(12) 0.0136(4) Uani 1 1 d . . . . .
C11 C 0.2550(2) 0.5353(3) 0.29641(13) 0.0175(5) Uani 1 1 d . . . . .
H11 H 0.1832 0.4762 0.2798 0.021 Uiso 1 1 calc R U . . .
C12 C 0.3196(2) 0.5686(3) 0.24638(13) 0.0191(5) Uani 1 1 d . . . . .
H12 H 0.2931 0.5292 0.1966 0.023 Uiso 1 1 calc R U . . .
C13 C 0.4234(2) 0.6598(3) 0.26912(12) 0.0184(5) Uani 1 1 d . . . . .
H13 H 0.4669 0.6862 0.2347 0.022 Uiso 1 1 calc R U . . .
C14 C 0.46191(19) 0.7108(3) 0.34156(12) 0.0151(5) Uani 1 1 d . . . . .
H14 H 0.5324 0.7739 0.3566 0.018 Uiso 1 1 calc R U . . .
C15 C 0.40037(19) 0.6729(3) 0.39511(12) 0.0131(4) Uani 1 1 d . . . . .
C16 C 0.45368(18) 0.7229(3) 0.47237(12) 0.0125(4) Uani 1 1 d . . . . .
N3 N 0.55945(16) 0.8008(2) 0.49144(11) 0.0148(4) Uani 1 1 d . . . . .
H3A H 0.609(2) 0.775(3) 0.4696(15) 0.023(7) Uiso 1 1 d . . . . .
C17 C 0.59730(19) 0.8251(3) 0.57189(12) 0.0154(5) Uani 1 1 d . . . . .
H17 H 0.6167 0.9486 0.5849 0.019 Uiso 1 1 calc R U . . .
H17A H 0.6651 0.7513 0.5945 0.019 Uiso 1 1 calc R U . . .
N4 N 0.40732(15) 0.7017(2) 0.52795(10) 0.0138(4) Uani 1 1 d . . . . .
C18 C 0.48997(19) 0.7670(3) 0.59635(12) 0.0172(5) Uani 1 1 d . . . . .
H18 H 0.5102 0.6737 0.6341 0.021 Uiso 1 1 calc R U . . .
H18A H 0.4564 0.8664 0.6174 0.021 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O2 1.9357(16) . ?
Co1 O1 1.9389(16) . ?
Co1 N4 1.9586(18) . ?
Co1 N2 1.9593(18) . ?
O1 C1 1.321(2) . ?
C1 C2 1.411(3) . ?
C1 C6 1.419(3) . ?
C2 C3 1.380(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.393(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.367(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.413(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.460(3) . ?
C7 N2 1.308(3) . ?
C7 N1 1.362(3) . ?
N1 C8 1.469(3) . ?
N1 H1 0.84(3) . ?
C8 C9 1.540(3) . ?
C8 H8 0.9900 . ?
C8 H8A 0.9900 . ?
C9 N2 1.472(3) . ?
C9 H9 0.9900 . ?
C9 H9A 0.9900 . ?
O2 C10 1.323(2) . ?
C10 C15 1.408(3) . ?
C10 C11 1.413(3) . ?
C11 C12 1.384(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.393(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.368(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.421(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.468(3) . ?
C16 N4 1.311(3) . ?
C16 N3 1.361(3) . ?
N3 C17 1.464(3) . ?
N3 H3A 0.83(3) . ?
C17 C18 1.540(3) . ?
C17 H17 0.9900 . ?
C17 H17A 0.9900 . ?
N4 C18 1.484(3) . ?
C18 H18 0.9900 . ?
C18 H18A 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Co1 O1 109.91(7) . . ?
O2 Co1 N4 94.25(7) . . ?
O1 Co1 N4 120.02(7) . . ?
O2 Co1 N2 113.33(7) . . ?
O1 Co1 N2 93.56(7) . . ?
N4 Co1 N2 126.30(8) . . ?
C1 O1 Co1 126.97(14) . . ?
O1 C1 C2 117.92(19) . . ?
O1 C1 C6 124.5(2) . . ?
C2 C1 C6 117.55(19) . . ?
C3 C2 C1 122.4(2) . . ?
C3 C2 H2 118.8 . . ?
C1 C2 H2 118.8 . . ?
C2 C3 C4 119.6(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 119.4(2) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 122.5(2) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C5 C6 C1 118.5(2) . . ?
C5 C6 C7 118.8(2) . . ?
C1 C6 C7 122.66(19) . . ?
N2 C7 N1 114.0(2) . . ?
N2 C7 C6 125.9(2) . . ?
N1 C7 C6 120.08(19) . . ?
C7 N1 C8 109.54(17) . . ?
C7 N1 H1 121.4(17) . . ?
C8 N1 H1 116.5(19) . . ?
N1 C8 C9 102.24(17) . . ?
N1 C8 H8 111.3 . . ?
C9 C8 H8 111.3 . . ?
N1 C8 H8A 111.3 . . ?
C9 C8 H8A 111.3 . . ?
H8 C8 H8A 109.2 . . ?
N2 C9 C8 105.31(17) . . ?
N2 C9 H9 110.7 . . ?
C8 C9 H9 110.7 . . ?
N2 C9 H9A 110.7 . . ?
C8 C9 H9A 110.7 . . ?
H9 C9 H9A 108.8 . . ?
C7 N2 C9 108.73(17) . . ?
C7 N2 Co1 125.00(15) . . ?
C9 N2 Co1 125.27(13) . . ?
C10 O2 Co1 126.85(15) . . ?
O2 C10 C15 124.4(2) . . ?
O2 C10 C11 117.4(2) . . ?
C15 C10 C11 118.21(19) . . ?
C12 C11 C10 121.8(2) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 119.9(2) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 119.2(2) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C15 122.4(2) . . ?
C13 C14 H14 118.8 . . ?
C15 C14 H14 118.8 . . ?
C10 C15 C14 118.3(2) . . ?
C10 C15 C16 123.81(18) . . ?
C14 C15 C16 117.9(2) . . ?
N4 C16 N3 114.0(2) . . ?
N4 C16 C15 125.6(2) . . ?
N3 C16 C15 120.46(18) . . ?
C16 N3 C17 109.94(18) . . ?
C16 N3 H3A 120.5(19) . . ?
C17 N3 H3A 117.7(19) . . ?
N3 C17 C18 102.14(17) . . ?
N3 C17 H17 111.3 . . ?
C18 C17 H17 111.3 . . ?
N3 C17 H17A 111.3 . . ?
C18 C17 H17A 111.3 . . ?
H17 C17 H17A 109.2 . . ?
C16 N4 C18 108.36(17) . . ?
C16 N4 Co1 124.50(16) . . ?
C18 N4 Co1 126.61(13) . . ?
N4 C18 C17 105.22(16) . . ?
N4 C18 H18 110.7 . . ?
C17 C18 H18 110.7 . . ?
N4 C18 H18A 110.7 . . ?
C17 C18 H18A 110.7 . . ?
H18 C18 H18A 108.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Co1 O1 C1 C2 -171.59(15) . . . . ?
Co1 O1 C1 C6 9.6(3) . . . . ?
O1 C1 C2 C3 180.0(2) . . . . ?
C6 C1 C2 C3 -1.1(3) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
C2 C3 C4 C5 1.7(4) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
C4 C5 C6 C1 -1.4(3) . . . . ?
C4 C5 C6 C7 178.0(2) . . . . ?
O1 C1 C6 C5 -179.0(2) . . . . ?
C2 C1 C6 C5 2.2(3) . . . . ?
O1 C1 C6 C7 1.7(3) . . . . ?
C2 C1 C6 C7 -177.2(2) . . . . ?
C5 C6 C7 N2 169.0(2) . . . . ?
C1 C6 C7 N2 -11.7(4) . . . . ?
C5 C6 C7 N1 -8.9(3) . . . . ?
C1 C6 C7 N1 170.5(2) . . . . ?
N2 C7 N1 C8 3.0(3) . . . . ?
C6 C7 N1 C8 -178.92(19) . . . . ?
C7 N1 C8 C9 -0.6(2) . . . . ?
N1 C8 C9 N2 -1.6(2) . . . . ?
N1 C7 N2 C9 -4.1(3) . . . . ?
C6 C7 N2 C9 178.0(2) . . . . ?
N1 C7 N2 Co1 -173.11(15) . . . . ?
C6 C7 N2 Co1 8.9(3) . . . . ?
C8 C9 N2 C7 3.4(2) . . . . ?
C8 C9 N2 Co1 172.41(15) . . . . ?
Co1 O2 C10 C15 -6.4(3) . . . . ?
Co1 O2 C10 C11 171.96(14) . . . . ?
O2 C10 C11 C12 -179.0(2) . . . . ?
C15 C10 C11 C12 -0.6(3) . . . . ?
C10 C11 C12 C13 -2.0(3) . . . . ?
C11 C12 C13 C14 2.0(3) . . . . ?
C12 C13 C14 C15 0.6(3) . . . . ?
O2 C10 C15 C14 -178.67(19) . . . . ?
C11 C10 C15 C14 3.0(3) . . . . ?
O2 C10 C15 C16 2.6(3) . . . . ?
C11 C10 C15 C16 -175.7(2) . . . . ?
C13 C14 C15 C10 -3.1(3) . . . . ?
C13 C14 C15 C16 175.7(2) . . . . ?
C10 C15 C16 N4 -3.2(3) . . . . ?
C14 C15 C16 N4 178.1(2) . . . . ?
C10 C15 C16 N3 177.9(2) . . . . ?
C14 C15 C16 N3 -0.9(3) . . . . ?
N4 C16 N3 C17 5.3(3) . . . . ?
C15 C16 N3 C17 -175.64(19) . . . . ?
C16 N3 C17 C18 -6.1(2) . . . . ?
N3 C16 N4 C18 -1.7(3) . . . . ?
C15 C16 N4 C18 179.21(19) . . . . ?
N3 C16 N4 Co1 -173.85(14) . . . . ?
C15 C16 N4 Co1 7.1(3) . . . . ?
C16 N4 C18 C17 -2.2(2) . . . . ?
Co1 N4 C18 C17 169.68(14) . . . . ?
N3 C17 C18 N4 4.9(2) . . . . ?

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
N1 H1 O2 0.84(3) 2.03(3) 2.845(3) 164(3) 3_566
N3 H3A O1 0.83(3) 2.03(3) 2.844(2) 165(2) 3_666

_refine_diff_density_max         0.736
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.086

