# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1548132'
_audit_update_record             
;
2018-05-26 deposited with the CCDC.
2018-07-17 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 H21 Co N10 O2'
_chemical_formula_sum            'C18 H21 Co N10 O2'
_chemical_formula_weight         468.38

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                   7.9648(3)
_cell_length_b                   7.9932(3)
_cell_length_c                   31.0201(11)
_cell_angle_alpha                90
_cell_angle_beta                 96.409(2)
_cell_angle_gamma                90
_cell_volume                     1962.53(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3998
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      26.38

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_F_000             968.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.295
_exptl_absorpt_coefficient_mu    0.915
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.711
_exptl_absorpt_correction_T_max  0.767
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25838
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.573
_diffrn_reflns_theta_max         25.068
_diffrn_reflns_theta_full        25.068
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3491
_reflns_number_gt                3158
_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 APEX II'
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_reduction        'BRUKER APEX II'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP 3v2'
_computing_publication_material  SHELXL
_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)+(0.0370P)²+4.4055P] 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         3469
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_ref         0.1219
_refine_ls_wR_factor_gt          0.1194
_refine_ls_goodness_of_fit_ref   1.185
_refine_ls_restrained_S_all      1.185
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.001

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 0.38250(6) 0.34205(6) 0.39932(2) 0.02773(16) Uani 1 1 d . . . . .
O1 O 0.1871(3) 0.3866(3) 0.36175(8) 0.0338(6) Uani 1 1 d . . . . .
O2 O 0.0163(4) 0.5036(4) 0.29121(9) 0.0459(8) Uani 1 1 d . . . . .
N2 N 0.2766(4) 0.4103(4) 0.44879(9) 0.0315(7) Uani 1 1 d . . . . .
N3 N 0.6055(4) 0.2799(4) 0.42754(9) 0.0308(7) Uani 1 1 d . . . . .
N4 N 0.6910(4) 0.2769(5) 0.46742(10) 0.0385(8) Uani 1 1 d . . . . .
N6 N 0.8685(4) 0.2076(4) 0.42129(11) 0.0392(8) Uani 1 1 d . . . . .
N7 N 0.4942(4) 0.2825(4) 0.34746(10) 0.0312(7) Uani 1 1 d . . . . .
N1Z N 0.4686(4) 0.5694(4) 0.39516(10) 0.0359(8) Uani 1 1 d . . . . .
N5 N 0.8470(4) 0.2337(5) 0.46323(11) 0.0435(9) Uani 1 1 d . . . . .
C18 C 0.7173(5) 0.2373(5) 0.40050(12) 0.0315(8) Uani 1 1 d . . . . .
C17 C 0.6580(5) 0.2363(5) 0.35450(12) 0.0335(9) Uani 1 1 d . . . . .
C13 C 0.4241(5) 0.2947(6) 0.30600(12) 0.0397(10) Uani 1 1 d . . . . .
H13 H 0.3124 0.3297 0.3004 0.048 Uiso 1 1 calc R U . . .
C14 C 0.5132(6) 0.2569(6) 0.27184(13) 0.0472(11) Uani 1 1 d . . . . .
H14 H 0.4619 0.2669 0.2435 0.057 Uiso 1 1 calc R U . . .
C15 C 0.6784(6) 0.2043(6) 0.27941(14) 0.0512(12) Uani 1 1 d . . . . .
H15 H 0.7380 0.1738 0.2565 0.061 Uiso 1 1 calc R U . . .
C16 C 0.7538(6) 0.1975(6) 0.32150(13) 0.0448(11) Uani 1 1 d . . . . .
H16 H 0.8668 0.1674 0.3275 0.054 Uiso 1 1 calc R U . . .
C7 C 0.0887(4) 0.5150(5) 0.36686(12) 0.0318(8) Uani 1 1 d . . . . .
C8 C -0.0101(5) 0.5801(5) 0.32949(13) 0.0365(9) Uani 1 1 d . . . . .
C12 C -0.0869(6) 0.5546(7) 0.25333(14) 0.0558(13) Uani 1 1 d . . . . .
H12A H -0.0566 0.4926 0.2289 0.084 Uiso 1 1 calc R U . . .
H12B H -0.2033 0.5340 0.2569 0.084 Uiso 1 1 calc R U . . .
H12C H -0.0708 0.6719 0.2486 0.084 Uiso 1 1 calc R U . . .
C9 C -0.1208(6) 0.7093(6) 0.33377(16) 0.0497(12) Uani 1 1 d . . . . .
H9 H -0.1855 0.7508 0.3093 0.060 Uiso 1 1 calc R U . . .
C10 C -0.1374(6) 0.7789(6) 0.37426(17) 0.0549(12) Uani 1 1 d . . . . .
H10 H -0.2121 0.8670 0.3766 0.066 Uiso 1 1 calc R U . . .
C11 C -0.0444(5) 0.7182(6) 0.41034(15) 0.0449(10) Uani 1 1 d . . . . .
H11 H -0.0561 0.7645 0.4373 0.054 Uiso 1 1 calc R U . . .
C6 C 0.0692(5) 0.5858(5) 0.40694(13) 0.0329(8) Uani 1 1 d . . . . .
C5 C 0.1540(5) 0.5151(5) 0.44609(13) 0.0364(9) Uani 1 1 d . . . . .
H5 H 0.1162 0.5487 0.4720 0.044 Uiso 1 1 calc R U . . .
C4 C 0.3248(5) 0.3273(6) 0.49075(13) 0.0438(11) Uani 1 1 d . . . . .
H4A H 0.2754 0.3864 0.5136 0.053 Uiso 1 1 calc R U . . .
H4B H 0.4467 0.3291 0.4975 0.053 Uiso 1 1 calc R U . . .
C3 C 0.2625(5) 0.1480(6) 0.48839(14) 0.0477(11) Uani 1 1 d . . . . .
H3A H 0.2978 0.0940 0.5159 0.057 Uiso 1 1 calc R U . . .
H3B H 0.1400 0.1491 0.4845 0.057 Uiso 1 1 calc R U . . .
C2 C 0.3234(5) 0.0449(5) 0.45279(14) 0.0453(11) Uani 1 1 d . . . . .
H2A H 0.4451 0.0326 0.4583 0.054 Uiso 1 1 calc R U . . .
H2B H 0.2740 -0.0659 0.4534 0.054 Uiso 1 1 calc R U . . .
N1 N 0.2809(4) 0.1178(4) 0.40879(11) 0.0406(8) Uani 1 1 d . . . . .
H1 H 0.1593 0.1399 0.4070 0.049 Uiso 1 1 calc R U . . .
C1 C 0.2956(7) -0.0050(6) 0.37606(17) 0.0642(14) Uani 1 1 d . . . . .
H1A H 0.2677 0.0445 0.3480 0.096 Uiso 1 1 calc R U . . .
H1B H 0.4094 -0.0463 0.3785 0.096 Uiso 1 1 calc R U . . .
H1C H 0.2196 -0.0958 0.3797 0.096 Uiso 1 1 calc R U . . .
N2Z N 0.4529(4) 0.6319(4) 0.35988(12) 0.0425(8) Uani 1 1 d . . . . .
N3Z N 0.4399(6) 0.6986(6) 0.32687(14) 0.0719(13) 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 1.872(2) . ?
Co1 N2 1.911(3) . ?
Co1 N1Z 1.952(3) . ?
Co1 N3 1.955(3) . ?
Co1 N7 1.981(3) . ?
Co1 N1 2.002(3) . ?
O1 C7 1.311(4) . ?
O2 C8 1.373(5) . ?
O2 C12 1.417(5) . ?
N2 C5 1.282(5) . ?
N2 C4 1.473(5) . ?
N3 C18 1.334(5) . ?
N3 N4 1.344(4) . ?
N4 N5 1.310(5) . ?
N6 C18 1.323(5) . ?
N6 N5 1.347(5) . ?
N7 C13 1.347(5) . ?
N7 C17 1.351(5) . ?
N1Z N2Z 1.196(5) . ?
C18 C17 1.452(5) . ?
C17 C16 1.379(6) . ?
C13 C14 1.373(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.376(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.376(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C7 C6 1.391(5) . ?
C7 C8 1.425(5) . ?
C8 C9 1.373(6) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C9 C10 1.394(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.361(6) . ?
C10 H10 0.9300 . ?
C11 C6 1.403(6) . ?
C11 H11 0.9300 . ?
C6 C5 1.438(5) . ?
C5 H5 0.9300 . ?
C4 C3 1.515(7) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C3 C2 1.501(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C2 N1 1.488(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
N1 C1 1.426(6) . ?
N1 H1 0.9800 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
N2Z N3Z 1.149(5) . ?

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 N2 92.00(12) . . ?
O1 Co1 N1Z 93.18(13) . . ?
N2 Co1 N1Z 88.69(14) . . ?
O1 Co1 N3 168.01(12) . . ?
N2 Co1 N3 99.98(13) . . ?
N1Z Co1 N3 87.58(14) . . ?
O1 Co1 N7 87.57(12) . . ?
N2 Co1 N7 177.31(14) . . ?
N1Z Co1 N7 88.68(14) . . ?
N3 Co1 N7 80.49(12) . . ?
O1 Co1 N1 86.57(13) . . ?
N2 Co1 N1 85.19(15) . . ?
N1Z Co1 N1 173.86(15) . . ?
N3 Co1 N1 93.93(14) . . ?
N7 Co1 N1 97.43(14) . . ?
C7 O1 Co1 122.7(2) . . ?
C8 O2 C12 117.3(3) . . ?
C5 N2 C4 118.2(3) . . ?
C5 N2 Co1 122.4(3) . . ?
C4 N2 Co1 119.1(3) . . ?
C18 N3 N4 105.6(3) . . ?
C18 N3 Co1 114.9(2) . . ?
N4 N3 Co1 139.3(3) . . ?
N5 N4 N3 107.6(3) . . ?
C18 N6 N5 103.6(3) . . ?
C13 N7 C17 117.7(3) . . ?
C13 N7 Co1 125.6(3) . . ?
C17 N7 Co1 116.6(2) . . ?
N2Z N1Z Co1 116.6(3) . . ?
N4 N5 N6 111.2(3) . . ?
N6 C18 N3 112.0(3) . . ?
N6 C18 C17 131.0(4) . . ?
N3 C18 C17 116.9(3) . . ?
N7 C17 C16 123.1(4) . . ?
N7 C17 C18 111.1(3) . . ?
C16 C17 C18 125.8(4) . . ?
N7 C13 C14 121.7(4) . . ?
N7 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C13 C14 C15 120.2(4) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C16 118.8(4) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C15 C16 C17 118.5(4) . . ?
C15 C16 H16 120.8 . . ?
C17 C16 H16 120.8 . . ?
O1 C7 C6 123.7(3) . . ?
O1 C7 C8 118.1(3) . . ?
C6 C7 C8 118.1(3) . . ?
O2 C8 C9 125.5(4) . . ?
O2 C8 C7 114.6(3) . . ?
C9 C8 C7 119.9(4) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C9 C10 120.9(4) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C11 C10 C9 120.1(4) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C6 120.2(4) . . ?
C10 C11 H11 119.9 . . ?
C6 C11 H11 119.9 . . ?
C7 C6 C11 120.8(4) . . ?
C7 C6 C5 120.4(4) . . ?
C11 C6 C5 118.6(4) . . ?
N2 C5 C6 126.5(4) . . ?
N2 C5 H5 116.8 . . ?
C6 C5 H5 116.8 . . ?
N2 C4 C3 109.4(3) . . ?
N2 C4 H4A 109.8 . . ?
C3 C4 H4A 109.8 . . ?
N2 C4 H4B 109.8 . . ?
C3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.2 . . ?
C2 C3 C4 115.1(4) . . ?
C2 C3 H3A 108.5 . . ?
C4 C3 H3A 108.5 . . ?
C2 C3 H3B 108.5 . . ?
C4 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
N1 C2 C3 113.6(4) . . ?
N1 C2 H2A 108.8 . . ?
C3 C2 H2A 108.8 . . ?
N1 C2 H2B 108.8 . . ?
C3 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C1 N1 C2 110.8(4) . . ?
C1 N1 Co1 116.4(3) . . ?
C2 N1 Co1 115.5(2) . . ?
C1 N1 H1 104.1 . . ?
C2 N1 H1 104.1 . . ?
Co1 N1 H1 104.1 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N3Z N2Z N1Z 176.9(5) . . ?

_refine_diff_density_max         0.683
_refine_diff_density_min         -0.919
_refine_diff_density_rms         0.070

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1548133'
_audit_update_record             
;
2018-05-26 deposited with the CCDC.
2018-07-17 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 H25 Co N10 O2'
_chemical_formula_sum            'C20 H25 Co N10 O2'
_chemical_formula_weight         496.43

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                   16.1282(4)
_cell_length_b                   7.7871(2)
_cell_length_c                   18.6891(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.1330(10)
_cell_angle_gamma                90
_cell_volume                     2276.15(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3982
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      25.0

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_F_000             1032.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    0.794
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.768
_exptl_absorpt_correction_T_max  0.828
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31148
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.247
_diffrn_reflns_theta_max         24.962
_diffrn_reflns_theta_full        24.962
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3995
_reflns_number_gt                3493
_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 APEX II'
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_reduction        'BRUKER APEX II'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP 3v2'
_computing_publication_material  SHELXL
_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)+(0.0387P)²+0.7168P] 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         3982
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0745
_refine_ls_wR_factor_gt          0.0714
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001

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 0.29747(2) 0.63413(3) 0.32784(2) 0.03019(9) Uani 1 1 d . . . . .
C2 C 0.28168(14) 1.0101(2) 0.34502(12) 0.0534(5) Uani 1 1 d . . . . .
H2A H 0.2809 1.0157 0.2936 0.080 Uiso 1 1 calc R U . . .
H2B H 0.2246 0.9920 0.3504 0.080 Uiso 1 1 calc R U . . .
H2C H 0.3036 1.1159 0.3686 0.080 Uiso 1 1 calc R U . . .
O1 O 0.18744(8) 0.72150(16) 0.29220(7) 0.0386(3) Uani 1 1 d . . . . .
N3 N 0.40175(9) 0.51698(17) 0.37807(8) 0.0339(3) Uani 1 1 d . . . . .
N4 N 0.47829(10) 0.4766(2) 0.36602(9) 0.0434(4) Uani 1 1 d . . . . .
N5 N 0.51429(11) 0.3627(2) 0.41572(10) 0.0471(4) Uani 1 1 d . . . . .
N7 N 0.25680(9) 0.53098(18) 0.41062(8) 0.0342(3) Uani 1 1 d . . . . .
O2 O 0.02295(8) 0.6901(2) 0.26530(8) 0.0551(4) Uani 1 1 d . . . . .
N1Z N 0.26015(10) 0.4177(2) 0.27752(9) 0.0402(4) Uani 1 1 d . . . . .
N2Z N 0.29724(11) 0.3627(2) 0.23426(9) 0.0441(4) Uani 1 1 d . . . . .
N6 N 0.46249(11) 0.3254(2) 0.46065(9) 0.0437(4) Uani 1 1 d . . . . .
C20 C 0.39476(12) 0.4230(2) 0.43583(10) 0.0343(4) Uani 1 1 d . . . . .
C19 C 0.31448(12) 0.4325(2) 0.45748(10) 0.0363(4) Uani 1 1 d . . . . .
C15 C 0.17735(13) 0.5417(3) 0.42011(11) 0.0455(5) Uani 1 1 d . . . . .
H15 H 0.1369 0.6077 0.3876 0.055 Uiso 1 1 calc R U . . .
C16 C 0.15428(15) 0.4569(3) 0.47713(12) 0.0590(6) Uani 1 1 d . . . . .
H16 H 0.0986 0.4647 0.4826 0.071 Uiso 1 1 calc R U . . .
C17 C 0.21406(17) 0.3608(3) 0.52568(13) 0.0640(7) Uani 1 1 d . . . . .
H17 H 0.1993 0.3047 0.5647 0.077 Uiso 1 1 calc R U . . .
C18 C 0.29579(16) 0.3479(3) 0.51640(12) 0.0527(5) Uani 1 1 d . . . . .
H18 H 0.3372 0.2841 0.5489 0.063 Uiso 1 1 calc R U . . .
N2 N 0.33161(10) 0.7190(2) 0.24365(9) 0.0405(4) Uani 1 1 d . . . . .
C5 C 0.42122(13) 0.7705(3) 0.25199(13) 0.0536(6) Uani 1 1 d . . . . .
H5A H 0.4306 0.7976 0.2039 0.064 Uiso 1 1 calc R U . . .
H5B H 0.4585 0.6757 0.2725 0.064 Uiso 1 1 calc R U . . .
C4 C 0.44307(14) 0.9249(3) 0.30187(14) 0.0620(6) Uani 1 1 d . . . . .
H4A H 0.5028 0.9529 0.3070 0.074 Uiso 1 1 calc R U . . .
H4B H 0.4095 1.0217 0.2781 0.074 Uiso 1 1 calc R U . . .
C3 C 0.42801(13) 0.9034(3) 0.37783(13) 0.0519(5) Uani 1 1 d . . . . .
H3A H 0.4642 0.8110 0.4026 0.062 Uiso 1 1 calc R U . . .
H3B H 0.4459 1.0078 0.4056 0.062 Uiso 1 1 calc R U . . .
N1 N 0.33737(10) 0.86509(18) 0.38002(9) 0.0392(4) Uani 1 1 d . . . . .
C1 C 0.33602(14) 0.8629(3) 0.45903(11) 0.0501(5) Uani 1 1 d . . . . .
H1A H 0.3713 0.7708 0.4836 0.075 Uiso 1 1 calc R U . . .
H1B H 0.3574 0.9702 0.4814 0.075 Uiso 1 1 calc R U . . .
H1C H 0.2784 0.8464 0.4632 0.075 Uiso 1 1 calc R U . . .
C6 C 0.27903(14) 0.7344(3) 0.18042(12) 0.0495(5) Uani 1 1 d . . . . .
H6 H 0.3016 0.7663 0.1411 0.059 Uiso 1 1 calc R U . . .
C7 C 0.18821(14) 0.7069(3) 0.16479(11) 0.0469(5) Uani 1 1 d . . . . .
C8 C 0.14691(12) 0.7042(2) 0.22265(10) 0.0397(4) Uani 1 1 d . . . . .
C9 C 0.05642(13) 0.6891(3) 0.20536(11) 0.0469(5) Uani 1 1 d . . . . .
C13 C -0.06731(13) 0.6718(4) 0.25413(14) 0.0656(7) Uani 1 1 d . . . . .
H13A H -0.0862 0.5646 0.2290 0.079 Uiso 1 1 calc R U . . .
H13B H -0.0966 0.7657 0.2242 0.079 Uiso 1 1 calc R U . . .
C14 C -0.08647(16) 0.6735(4) 0.32778(15) 0.0748(8) Uani 1 1 d . . . . .
H14A H -0.1470 0.6613 0.3221 0.112 Uiso 1 1 calc R U . . .
H14B H -0.0572 0.5800 0.3568 0.112 Uiso 1 1 calc R U . . .
H14C H -0.0676 0.7801 0.3521 0.112 Uiso 1 1 calc R U . . .
C10 C 0.01110(16) 0.6735(3) 0.13318(13) 0.0622(6) Uani 1 1 d . . . . .
H10 H -0.0481 0.6618 0.1222 0.075 Uiso 1 1 calc R U . . .
C11 C 0.05315(19) 0.6752(4) 0.07649(14) 0.0725(7) Uani 1 1 d . . . . .
H11 H 0.0218 0.6649 0.0278 0.087 Uiso 1 1 calc R U . . .
C12 C 0.13919(18) 0.6917(3) 0.09144(12) 0.0654(7) Uani 1 1 d . . . . .
H12 H 0.1663 0.6930 0.0529 0.079 Uiso 1 1 calc R U . . .
N3Z N 0.32870(15) 0.3031(3) 0.19143(12) 0.0786(7) 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 1.8650(12) . ?
Co1 N2 1.9076(15) . ?
Co1 N3 1.9420(14) . ?
Co1 N1Z 1.9520(15) . ?
Co1 N7 1.9911(14) . ?
Co1 N1 2.0721(14) . ?
C2 N1 1.491(2) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
O1 C8 1.312(2) . ?
N3 C20 1.332(2) . ?
N3 N4 1.345(2) . ?
N4 N5 1.313(2) . ?
N5 N6 1.353(2) . ?
N7 C15 1.338(2) . ?
N7 C19 1.350(2) . ?
O2 C9 1.357(2) . ?
O2 C13 1.426(2) . ?
N1Z N2Z 1.196(2) . ?
N2Z N3Z 1.145(2) . ?
N6 C20 1.319(2) . ?
C20 C19 1.450(3) . ?
C19 C18 1.378(3) . ?
C15 C16 1.380(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.373(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.374(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
N2 C6 1.281(3) . ?
N2 C5 1.471(2) . ?
C5 C4 1.509(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C4 C3 1.507(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C3 N1 1.502(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
N1 C1 1.482(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C6 C7 1.438(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.402(3) . ?
C7 C12 1.410(3) . ?
C8 C9 1.421(3) . ?
C9 C10 1.374(3) . ?
C13 C14 1.483(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C10 C11 1.391(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.353(4) . ?
C11 H11 0.9300 . ?
C12 H12 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 N2 91.16(6) . . ?
O1 Co1 N3 168.58(6) . . ?
N2 Co1 N3 99.86(6) . . ?
O1 Co1 N1Z 89.33(6) . . ?
N2 Co1 N1Z 91.08(7) . . ?
N3 Co1 N1Z 87.48(6) . . ?
O1 Co1 N7 87.67(6) . . ?
N2 Co1 N7 175.47(6) . . ?
N3 Co1 N7 81.12(6) . . ?
N1Z Co1 N7 84.53(6) . . ?
O1 Co1 N1 90.60(6) . . ?
N2 Co1 N1 88.19(7) . . ?
N3 Co1 N1 92.72(6) . . ?
N1Z Co1 N1 179.27(6) . . ?
N7 Co1 N1 96.19(6) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C8 O1 Co1 121.13(11) . . ?
C20 N3 N4 105.68(14) . . ?
C20 N3 Co1 114.54(12) . . ?
N4 N3 Co1 138.65(12) . . ?
N5 N4 N3 107.74(15) . . ?
N4 N5 N6 110.56(15) . . ?
C15 N7 C19 118.67(16) . . ?
C15 N7 Co1 125.83(13) . . ?
C19 N7 Co1 115.33(11) . . ?
C9 O2 C13 118.43(16) . . ?
N2Z N1Z Co1 119.23(13) . . ?
N3Z N2Z N1Z 175.8(2) . . ?
C20 N6 N5 103.99(15) . . ?
N6 C20 N3 112.03(16) . . ?
N6 C20 C19 130.62(17) . . ?
N3 C20 C19 117.15(15) . . ?
N7 C19 C18 122.64(18) . . ?
N7 C19 C20 111.64(15) . . ?
C18 C19 C20 125.68(18) . . ?
N7 C15 C16 121.3(2) . . ?
N7 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C17 C16 C15 119.5(2) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 119.8(2) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C19 118.0(2) . . ?
C17 C18 H18 121.0 . . ?
C19 C18 H18 121.0 . . ?
C6 N2 C5 118.97(17) . . ?
C6 N2 Co1 122.28(14) . . ?
C5 N2 Co1 118.75(13) . . ?
N2 C5 C4 110.96(17) . . ?
N2 C5 H5A 109.4 . . ?
C4 C5 H5A 109.4 . . ?
N2 C5 H5B 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C3 C4 C5 115.24(17) . . ?
C3 C4 H4A 108.5 . . ?
C5 C4 H4A 108.5 . . ?
C3 C4 H4B 108.5 . . ?
C5 C4 H4B 108.5 . . ?
H4A C4 H4B 107.5 . . ?
N1 C3 C4 115.44(18) . . ?
N1 C3 H3A 108.4 . . ?
C4 C3 H3A 108.4 . . ?
N1 C3 H3B 108.4 . . ?
C4 C3 H3B 108.4 . . ?
H3A C3 H3B 107.5 . . ?
C1 N1 C2 106.97(15) . . ?
C1 N1 C3 106.30(16) . . ?
C2 N1 C3 108.89(15) . . ?
C1 N1 Co1 112.37(11) . . ?
C2 N1 Co1 111.48(12) . . ?
C3 N1 Co1 110.60(12) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N2 C6 C7 125.85(18) . . ?
N2 C6 H6 117.1 . . ?
C7 C6 H6 117.1 . . ?
C8 C7 C12 119.3(2) . . ?
C8 C7 C6 119.85(18) . . ?
C12 C7 C6 120.8(2) . . ?
O1 C8 C7 123.18(18) . . ?
O1 C8 C9 118.01(17) . . ?
C7 C8 C9 118.75(18) . . ?
O2 C9 C10 126.0(2) . . ?
O2 C9 C8 113.91(17) . . ?
C10 C9 C8 120.1(2) . . ?
O2 C13 C14 107.45(19) . . ?
O2 C13 H13A 110.2 . . ?
C14 C13 H13A 110.2 . . ?
O2 C13 H13B 110.2 . . ?
C14 C13 H13B 110.2 . . ?
H13A C13 H13B 108.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C9 C10 C11 120.4(2) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 120.7(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 120.8(2) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?

_refine_diff_density_max         0.199
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.041

