# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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 1566997'
_audit_update_record             
;
2017-09-05 deposited with the CCDC.
2017-09-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H15 Co N4 O2 S2, C2 H4 O'
_chemical_formula_sum            'C15 H19 Co N4 O3 S2'
_chemical_formula_weight         426.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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                   10.088(3)
_cell_length_b                   12.859(3)
_cell_length_c                   14.791(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.505(3)
_cell_angle_gamma                90
_cell_volume                     1912.9(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1362
_cell_measurement_theta_min      2.025
_cell_measurement_theta_max      25.813

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            PINK
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_F_000             880.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    1.136
_shelx_estimated_absorpt_T_min   0.4959
_shelx_estimated_absorpt_T_max   0.7453
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4959
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_absorpt_special_details   SADABS
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Apex II'
_diffrn_measurement_method       'Omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13248
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_av_R_equivalents  0.0923
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.025
_diffrn_reflns_theta_max         25.813
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3626
_reflns_number_gt                2607
_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 Apex II'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Mercury 3.8'
_computing_publication_material  'Shelxl 2016/6'
_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)+(0.0452P)²+1.2877P] 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         3626
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1357
_refine_ls_wR_factor_gt          0.1214
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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 0.38568(5) 0.33403(3) 0.66403(3) 0.05029(18) Uani 1 1 d . . . . .
S1 S 0.03444(13) 0.17468(12) 0.49587(8) 0.0922(4) Uani 1 1 d . . . . .
S2 S 0.70245(14) 0.46374(10) 0.88079(9) 0.0891(4) Uani 1 1 d . . . . .
O1 O 0.3288(3) 0.47096(18) 0.63491(17) 0.0579(6) Uani 1 1 d . . . . .
O3 O 0.6769(3) 0.4759(2) 0.54764(19) 0.0743(8) Uani 1 1 d . . . . .
H3A H 0.651621 0.528813 0.520624 0.111 Uiso 1 1 calc R U . A 2
N1 N 0.2890(3) 0.3177(2) 0.7657(2) 0.0551(7) Uani 1 1 d . . . . .
N2 N 0.4473(3) 0.1930(2) 0.6876(2) 0.0563(8) Uani 1 1 d . . . . .
H2 H 0.382783 0.147053 0.654537 0.068 Uiso 1 1 calc R U . . .
O2 O 0.4997(3) 0.33149(19) 0.56149(18) 0.0601(7) Uani 1 1 d . . . . .
H2A H 0.556(5) 0.377(4) 0.560(3) 0.090 Uiso 1 1 d . U . . .
N4 N 0.5274(3) 0.3881(2) 0.7417(2) 0.0575(8) Uani 1 1 d . . . . .
N3 N 0.2441(4) 0.2793(3) 0.5873(2) 0.0686(9) Uani 1 1 d . . . . .
C1 C 0.2473(4) 0.5253(3) 0.6814(2) 0.0521(8) Uani 1 1 d . . . . .
C2 C 0.2142(4) 0.6271(3) 0.6523(3) 0.0626(10) Uani 1 1 d . . . . .
H2B H 0.250462 0.653336 0.601139 0.075 Uiso 1 1 calc R U . . .
C3 C 0.1300(4) 0.6883(3) 0.6974(3) 0.0711(12) Uani 1 1 d . . . . .
H3 H 0.109760 0.754862 0.676060 0.085 Uiso 1 1 calc R U . . .
C4 C 0.0749(5) 0.6528(4) 0.7737(3) 0.0774(13) Uani 1 1 d . . . . .
H4 H 0.018814 0.695309 0.804359 0.093 Uiso 1 1 calc R U . . .
C5 C 0.1040(4) 0.5534(3) 0.8041(3) 0.0680(11) Uani 1 1 d . . . . .
H5 H 0.065593 0.528715 0.855079 0.082 Uiso 1 1 calc R U . . .
C6 C 0.1901(4) 0.4887(3) 0.7598(2) 0.0547(9) Uani 1 1 d . . . . .
C7 C 0.2151(4) 0.3873(3) 0.7973(3) 0.0588(9) Uani 1 1 d . . . . .
H7 H 0.173874 0.370585 0.849495 0.071 Uiso 1 1 calc R U . . .
C8 C 0.3067(4) 0.2139(3) 0.8075(3) 0.0696(11) Uani 1 1 d . . . . .
H8A H 0.235540 0.167875 0.784794 0.084 Uiso 1 1 calc R U . . .
H8B H 0.305016 0.219082 0.872830 0.084 Uiso 1 1 calc R U . . .
C9 C 0.4377(5) 0.1721(3) 0.7838(3) 0.0675(11) Uani 1 1 d . . . . .
H9A H 0.509671 0.206113 0.819767 0.081 Uiso 1 1 calc R U . . .
H9B H 0.442763 0.097942 0.795502 0.081 Uiso 1 1 calc R U . . .
C10 C 0.5727(5) 0.1794(3) 0.6462(3) 0.0707(11) Uani 1 1 d . . . . .
H10A H 0.592683 0.106019 0.640606 0.085 Uiso 1 1 calc R U . . .
H10B H 0.644585 0.211889 0.683463 0.085 Uiso 1 1 calc R U . . .
C11 C 0.5589(5) 0.2289(3) 0.5550(3) 0.0741(12) Uani 1 1 d . . . . .
H11A H 0.645639 0.234929 0.531422 0.089 Uiso 1 1 calc R U . . .
H11B H 0.503277 0.185930 0.513607 0.089 Uiso 1 1 calc R U . . .
C12 C 0.8632(10) 0.4166(8) 0.6221(8) 0.200(4) Uani 1 1 d . . . . .
H12A H 0.817355 0.440389 0.672676 0.300 Uiso 1 1 calc R U . B 1
H12B H 0.949491 0.391088 0.643366 0.300 Uiso 1 1 calc R U . B 1
H12C H 0.813103 0.361680 0.591564 0.300 Uiso 1 1 calc R U . B 1
C13A C 0.877(3) 0.4982(16) 0.5624(14) 0.115(8) Uiso 0.40(3) 1 d . . P C 1
C13B C 0.8067(15) 0.4873(8) 0.5796(7) 0.084(5) Uiso 0.60(3) 1 d . . P C 2
C14 C 0.5988(4) 0.4188(3) 0.8001(3) 0.0585(9) Uani 1 1 d . . . . .
C15 C 0.1572(4) 0.2362(3) 0.5497(2) 0.0584(9) 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 N1 1.867(3) . ?
Co1 N3 1.889(4) . ?
Co1 O1 1.891(2) . ?
Co1 N4 1.894(4) . ?
Co1 N2 1.940(3) . ?
Co1 O2 1.974(3) . ?
S1 C15 1.624(5) . ?
S2 C14 1.630(5) . ?
O1 C1 1.314(4) . ?
O3 C13B 1.365(14) . ?
O3 H3A 0.8200 . ?
N1 C7 1.276(5) . ?
N1 C8 1.477(5) . ?
N2 C10 1.459(5) . ?
N2 C9 1.460(5) . ?
N2 H2 0.9800 . ?
O2 C11 1.455(4) . ?
O2 H2A 0.82(5) . ?
N4 C14 1.150(5) . ?
N3 C15 1.145(5) . ?
C1 C2 1.409(5) . ?
C1 C6 1.416(5) . ?
C2 C3 1.369(5) . ?
C2 H2B 0.9300 . ?
C3 C4 1.374(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.402(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.432(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.493(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.487(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13B 1.220(12) . ?
C12 C13A 1.39(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Co1 N3 91.35(15) . . ?
N1 Co1 O1 96.87(12) . . ?
N3 Co1 O1 90.48(13) . . ?
N1 Co1 N4 88.31(13) . . ?
N3 Co1 N4 179.57(14) . . ?
O1 Co1 N4 89.83(12) . . ?
N1 Co1 N2 86.04(13) . . ?
N3 Co1 N2 88.62(14) . . ?
O1 Co1 N2 176.98(12) . . ?
N4 Co1 N2 91.09(13) . . ?
N1 Co1 O2 171.65(12) . . ?
N3 Co1 O2 89.48(14) . . ?
O1 Co1 O2 91.43(10) . . ?
N4 Co1 O2 90.82(13) . . ?
N2 Co1 O2 85.67(12) . . ?
C1 O1 Co1 124.5(2) . . ?
C13B O3 H3A 109.5 . . ?
C7 N1 C8 122.3(3) . . ?
C7 N1 Co1 125.0(3) . . ?
C8 N1 Co1 112.6(2) . . ?
C10 N2 C9 120.9(3) . . ?
C10 N2 Co1 108.2(2) . . ?
C9 N2 Co1 107.6(2) . . ?
C10 N2 H2 106.4 . . ?
C9 N2 H2 106.4 . . ?
Co1 N2 H2 106.4 . . ?
C11 O2 Co1 109.4(2) . . ?
C11 O2 H2A 111(3) . . ?
Co1 O2 H2A 117(3) . . ?
C14 N4 Co1 168.4(3) . . ?
C15 N3 Co1 170.8(3) . . ?
O1 C1 C2 118.5(3) . . ?
O1 C1 C6 124.3(3) . . ?
C2 C1 C6 117.2(3) . . ?
C3 C2 C1 121.7(4) . . ?
C3 C2 H2B 119.1 . . ?
C1 C2 H2B 119.1 . . ?
C2 C3 C4 121.1(4) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 119.1(4) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C4 C5 C6 121.4(4) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 119.5(3) . . ?
C5 C6 C7 117.1(3) . . ?
C1 C6 C7 123.3(3) . . ?
N1 C7 C6 125.9(3) . . ?
N1 C7 H7 117.1 . . ?
C6 C7 H7 117.1 . . ?
N1 C8 C9 107.9(3) . . ?
N1 C8 H8A 110.1 . . ?
C9 C8 H8A 110.1 . . ?
N1 C8 H8B 110.1 . . ?
C9 C8 H8B 110.1 . . ?
H8A C8 H8B 108.4 . . ?
N2 C9 C8 106.9(3) . . ?
N2 C9 H9A 110.3 . . ?
C8 C9 H9A 110.3 . . ?
N2 C9 H9B 110.3 . . ?
C8 C9 H9B 110.3 . . ?
H9A C9 H9B 108.6 . . ?
N2 C10 C11 107.9(3) . . ?
N2 C10 H10A 110.1 . . ?
C11 C10 H10A 110.1 . . ?
N2 C10 H10B 110.1 . . ?
C11 C10 H10B 110.1 . . ?
H10A C10 H10B 108.4 . . ?
O2 C11 C10 109.7(3) . . ?
O2 C11 H11A 109.7 . . ?
C10 C11 H11A 109.7 . . ?
O2 C11 H11B 109.7 . . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C13A C12 H12A 109.5 . . ?
C13A C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C13A C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C12 C13B O3 119.7(11) . . ?
N4 C14 S2 178.4(4) . . ?
N3 C15 S1 179.7(4) . . ?

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
C7 H7 S1 0.93 2.74 3.664(4) 175.6 4_566
O2 H2A O3 0.82(5) 1.78(5) 2.597(4) 175(5) .
N2 H2 S2 0.98 2.55 3.428(3) 149.2 2_646
O3 H3A O2 0.82 2.60 3.386(4) 162.1 3_666
O3 H3A O1 0.82 2.32 2.782(4) 115.8 3_666
C7 H7 S1 0.93 2.74 3.664(4) 175.6 4_566
O2 H2A O3 0.82(5) 1.78(5) 2.597(4) 175(5) .
N2 H2 S2 0.98 2.55 3.428(3) 149.2 2_646
O3 H3A O2 0.82 2.60 3.386(4) 162.1 3_666
O3 H3A O1 0.82 2.32 2.782(4) 115.8 3_666
C7 H7 S1 0.93 2.74 3.664(4) 175.6 4_566
O2 H2A O3 0.82(5) 1.78(5) 2.597(4) 175(5) .
N2 H2 S2 0.98 2.55 3.428(3) 149.2 2_646
C7 H7 S1 0.93 2.74 3.664(4) 175.6 4_566
O2 H2A O3 0.82(5) 1.78(5) 2.597(4) 175(5) .
N2 H2 S2 0.98 2.55 3.428(3) 149.2 2_646
O3 H3A O1 0.82 2.32 2.782(4) 115.8 3_666
C7 H7 S1 0.93 2.74 3.664(4) 175.6 4_566
O2 H2A O3 0.82(5) 1.78(5) 2.597(4) 175(5) .
N2 H2 S2 0.98 2.55 3.428(3) 149.2 2_646
O3 H3A O1 0.82 2.32 2.782(4) 115.8 3_666
C7 H7 S1 0.93 2.74 3.664(4) 175.6 4_566
O2 H2A O3 0.82(5) 1.78(5) 2.597(4) 175(5) .
N2 H2 S2 0.98 2.55 3.428(3) 149.2 2_646
C7 H7 S1 0.93 2.74 3.664(4) 175.6 4_566
O2 H2A O3 0.82(5) 1.78(5) 2.597(4) 175(5) .
N2 H2 S2 0.98 2.55 3.428(3) 149.2 2_646
O3 H3A O1 0.82 2.32 2.782(4) 115.8 3_666
C7 H7 S1 0.93 2.74 3.664(4) 175.6 4_566
O2 H2A O3 0.82(5) 1.78(5) 2.597(4) 175(5) .
N2 H2 S2 0.98 2.55 3.428(3) 149.2 2_646
O3 H3A O1 0.82 2.32 2.782(4) 115.8 3_666
O3 H3A O1 0.82 2.32 2.782(4) 115.8 3_666
N2 H2 S2 0.98 2.55 3.428(3) 149.2 2_646
O2 H2A O3 0.82(5) 1.78(5) 2.597(4) 175(5) .
C7 H7 S1 0.93 2.74 3.664(4) 175.6 4_566
O3 H3A O1 0.82 2.32 2.782(4) 115.8 3_666
N2 H2 S2 0.98 2.55 3.428(3) 149.2 2_646
O2 H2A O3 0.82(5) 1.78(5) 2.597(4) 175(5) .
C7 H7 S1 0.93 2.74 3.664(4) 175.6 4_566
O3 H3A O1 0.82 2.32 2.782(4) 115.8 3_666
N2 H2 S2 0.98 2.55 3.428(3) 149.2 2_646
O2 H2A O3 0.82(5) 1.78(5) 2.597(4) 175(5) .
C7 H7 S1 0.93 2.74 3.664(4) 175.6 4_566
O3 H3A O1 0.82 2.32 2.782(4) 115.8 3_666
N2 H2 S2 0.98 2.55 3.428(3) 149.2 2_646
O2 H2A O3 0.82(5) 1.78(5) 2.597(4) 175(5) .
C7 H7 S1 0.93 2.74 3.664(4) 175.6 4_566
O3 H3A O1 0.82 2.32 2.782(4) 115.8 3_666
O3 H3A O2 0.82 2.60 3.386(4) 162.1 3_666
N2 H2 S2 0.98 2.55 3.428(3) 149.2 2_646
O2 H2A O3 0.82(5) 1.78(5) 2.597(4) 175(5) .
C7 H7 S1 0.93 2.74 3.664(4) 175.6 4_566

_refine_diff_density_max         0.545
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.065

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1566999'
_audit_update_record             
;
2017-09-05 deposited with the CCDC.
2017-09-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H17 Co N4 O2 S2, C2 H5 O'
_chemical_formula_sum            'C16 H22 Co N4 O3 S2'
_chemical_formula_weight         441.43

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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.3859(8)
_cell_length_b                   11.4440(11)
_cell_length_c                   11.5557(12)
_cell_angle_alpha                65.724(3)
_cell_angle_beta                 84.537(3)
_cell_angle_gamma                78.011(3)
_cell_volume                     988.81(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    674
_cell_measurement_theta_min      1.933
_cell_measurement_theta_max      25.986

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            PINK
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_F_000             458.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    1.102
_shelx_estimated_absorpt_T_min   0.5856
_shelx_estimated_absorpt_T_max   0.7453
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5856
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_absorpt_special_details   SADABS
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Apex II'
_diffrn_measurement_method       'Omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12248
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.933
_diffrn_reflns_theta_max         25.986
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3832
_reflns_number_gt                3122
_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 Apex II'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Mercury 3.8'
_computing_publication_material  'Shelxl 2016/6'
_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)+(0.0565P)²+0.5017P] 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         3832
_refine_ls_number_parameters     239
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1092
_refine_ls_wR_factor_gt          0.1022
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.038
_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 0.35987(4) 0.24878(4) 0.23799(3) 0.03749(14) Uani 1 1 d D . . . .
S1 S 0.79449(12) -0.03276(10) 0.16584(11) 0.0777(3) Uani 1 1 d . . . . .
S2 S 0.84247(10) 0.32887(10) 0.32072(9) 0.0632(3) Uani 1 1 d . . . . .
O1 O 0.2116(2) 0.34966(18) 0.30402(17) 0.0406(4) Uani 1 1 d . . . . .
O2 O 0.3772(3) 0.1161(2) 0.40934(19) 0.0494(5) Uani 1 1 d D . . . .
H2 H 0.400(3) 0.130(3) 0.4745(14) 0.074 Uiso 1 1 d D U . . .
O3A O 0.4429(10) 0.1848(5) 0.5855(4) 0.060(2) Uiso 0.553(16) 1 d . . P A 1
O3B O 0.3583(16) 0.2136(8) 0.5790(6) 0.077(3) Uiso 0.447(16) 1 d . . P A 2
N1 N 0.3289(3) 0.3786(2) 0.0735(2) 0.0417(5) Uani 1 1 d . . . . .
N2 N 0.1826(3) 0.1740(2) 0.2201(2) 0.0472(6) Uani 1 1 d . . . . .
H2A H 0.081713 0.231087 0.228693 0.057 Uiso 1 1 calc R U . . .
N3 N 0.5365(3) 0.3124(2) 0.2677(2) 0.0465(6) Uani 1 1 d . . . . .
N4 N 0.5137(3) 0.1325(3) 0.1854(2) 0.0513(6) Uani 1 1 d . . . . .
C1 C 0.2034(3) 0.4752(3) 0.2643(3) 0.0413(6) Uani 1 1 d . . . . .
C2 C 0.1364(4) 0.5360(3) 0.3447(3) 0.0588(8) Uani 1 1 d . . . . .
H2B H 0.102089 0.486369 0.425952 0.071 Uiso 1 1 calc R U . . .
C3 C 0.1205(5) 0.6673(4) 0.3059(4) 0.0711(10) Uani 1 1 d . . . . .
H3 H 0.076361 0.705988 0.361468 0.085 Uiso 1 1 calc R U . . .
C4 C 0.1684(5) 0.7436(4) 0.1867(4) 0.0701(10) Uani 1 1 d . . . . .
H4 H 0.158039 0.833122 0.161693 0.084 Uiso 1 1 calc R U . . .
C5 C 0.2308(4) 0.6876(3) 0.1056(3) 0.0575(8) Uani 1 1 d . . . . .
H5 H 0.260842 0.739583 0.023813 0.069 Uiso 1 1 calc R U . . .
C6 C 0.2511(3) 0.5527(3) 0.1425(3) 0.0436(7) Uani 1 1 d . . . . .
C7 C 0.2927(3) 0.4992(3) 0.0512(3) 0.0461(7) Uani 1 1 d . . . . .
H7 H 0.293839 0.557619 -0.033312 0.055 Uiso 1 1 calc R U . . .
C8 C 0.3213(4) 0.3393(4) -0.0312(3) 0.0559(8) Uani 1 1 d . . . . .
H8A H 0.416734 0.274507 -0.030735 0.067 Uiso 1 1 calc R U . . .
H8B H 0.318712 0.414114 -0.111711 0.067 Uiso 1 1 calc R U . . .
C9 C 0.1704(4) 0.2836(4) -0.0146(3) 0.0645(9) Uani 1 1 d . . . . .
H9A H 0.077242 0.347445 -0.009019 0.077 Uiso 1 1 calc R U . . .
H9B H 0.156929 0.268178 -0.089284 0.077 Uiso 1 1 calc R U . . .
C10 C 0.1708(4) 0.1597(4) 0.0996(3) 0.0635(9) Uani 1 1 d . . . . .
H10A H 0.071504 0.128051 0.101232 0.076 Uiso 1 1 calc R U . . .
H10B H 0.262085 0.094766 0.093194 0.076 Uiso 1 1 calc R U . . .
C11 C 0.1875(5) 0.0479(3) 0.3299(3) 0.0638(9) Uani 1 1 d . . . . .
H11A H 0.267674 -0.019054 0.315004 0.077 Uiso 1 1 calc R U . . .
H11B H 0.081892 0.022209 0.342566 0.077 Uiso 1 1 calc R U . . .
C12 C 0.2317(4) 0.0627(3) 0.4444(3) 0.0632(9) Uani 1 1 d D . . . .
H12A H 0.145422 0.121052 0.466676 0.076 Uiso 1 1 calc R U . . .
H12B H 0.250862 -0.021094 0.516132 0.076 Uiso 1 1 calc R U . . .
C13 C 0.6303(4) 0.0642(3) 0.1780(3) 0.0479(7) Uani 1 1 d . . . . .
C14 C 0.6648(3) 0.3161(3) 0.2911(3) 0.0412(6) Uani 1 1 d . . . . .
C15 C 0.4231(8) 0.3547(6) 0.6601(5) 0.125(2) Uani 1 1 d . . . . .
H15A H 0.307877 0.387718 0.651826 0.188 Uiso 1 1 calc R U . . .
H15B H 0.479681 0.425419 0.641127 0.188 Uiso 1 1 calc R U . . .
H15C H 0.446582 0.292094 0.745411 0.188 Uiso 1 1 calc R U . . .
C16 C 0.4724(9) 0.2971(6) 0.5787(6) 0.135(2) Uani 1 1 d . . . . .
H16A H 0.432596 0.361461 0.496347 0.162 Uiso 1 1 calc R U . A 1
H16B H 0.590151 0.288188 0.573988 0.162 Uiso 1 1 calc R U . A 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 O1 1.8463(18) . ?
Co1 N1 1.871(2) . ?
Co1 N3 1.896(2) . ?
Co1 N4 1.899(3) . ?
Co1 N2 1.928(2) . ?
Co1 O2 1.933(2) . ?
S1 C13 1.613(3) . ?
S2 C14 1.609(3) . ?
O1 C1 1.305(3) . ?
O2 C12 1.428(4) . ?
O2 H2 0.873(9) . ?
O3A C16 1.328(7) . ?
O3B C16 1.485(10) . ?
N1 C7 1.270(4) . ?
N1 C8 1.464(4) . ?
N2 C11 1.474(4) . ?
N2 C10 1.483(4) . ?
N2 H2A 0.9800 . ?
N3 C14 1.147(4) . ?
N4 C13 1.138(4) . ?
C1 C2 1.391(4) . ?
C1 C6 1.393(4) . ?
C2 C3 1.361(5) . ?
C2 H2B 0.9300 . ?
C3 C4 1.369(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.350(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.399(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.408(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.494(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.487(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.489(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C15 C16 1.347(7) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Co1 N1 91.47(9) . . ?
O1 Co1 N3 91.86(10) . . ?
N1 Co1 N3 92.84(10) . . ?
O1 Co1 N4 174.68(10) . . ?
N1 Co1 N4 93.83(11) . . ?
N3 Co1 N4 88.33(11) . . ?
O1 Co1 N2 88.11(9) . . ?
N1 Co1 N2 91.39(10) . . ?
N3 Co1 N2 175.77(10) . . ?
N4 Co1 N2 91.31(11) . . ?
O1 Co1 O2 86.07(9) . . ?
N1 Co1 O2 176.39(9) . . ?
N3 Co1 O2 89.89(10) . . ?
N4 Co1 O2 88.61(10) . . ?
N2 Co1 O2 85.89(10) . . ?
C1 O1 Co1 122.33(17) . . ?
C12 O2 Co1 110.00(19) . . ?
C12 O2 H2 105.2(15) . . ?
Co1 O2 H2 123.5(16) . . ?
C7 N1 C8 118.3(3) . . ?
C7 N1 Co1 122.5(2) . . ?
C8 N1 Co1 118.5(2) . . ?
C11 N2 C10 111.0(3) . . ?
C11 N2 Co1 107.32(19) . . ?
C10 N2 Co1 118.1(2) . . ?
C11 N2 H2A 106.6 . . ?
C10 N2 H2A 106.6 . . ?
Co1 N2 H2A 106.6 . . ?
C14 N3 Co1 160.7(3) . . ?
C13 N4 Co1 161.4(3) . . ?
O1 C1 C2 118.7(3) . . ?
O1 C1 C6 123.1(3) . . ?
C2 C1 C6 118.2(3) . . ?
C3 C2 C1 120.8(3) . . ?
C3 C2 H2B 119.6 . . ?
C1 C2 H2B 119.6 . . ?
C2 C3 C4 121.2(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 119.3(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 121.1(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 119.4(3) . . ?
C1 C6 C7 119.9(3) . . ?
C5 C6 C7 119.9(3) . . ?
N1 C7 C6 126.1(3) . . ?
N1 C7 H7 117.0 . . ?
C6 C7 H7 117.0 . . ?
N1 C8 C9 108.3(2) . . ?
N1 C8 H8A 110.0 . . ?
C9 C8 H8A 110.0 . . ?
N1 C8 H8B 110.0 . . ?
C9 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
C10 C9 C8 114.1(3) . . ?
C10 C9 H9A 108.7 . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
N2 C10 C9 113.1(3) . . ?
N2 C10 H10A 109.0 . . ?
C9 C10 H10A 109.0 . . ?
N2 C10 H10B 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
N2 C11 C12 108.4(3) . . ?
N2 C11 H11A 110.0 . . ?
C12 C11 H11A 110.0 . . ?
N2 C11 H11B 110.0 . . ?
C12 C11 H11B 110.0 . . ?
H11A C11 H11B 108.4 . . ?
O2 C12 C11 105.1(3) . . ?
O2 C12 H12A 110.7 . . ?
C11 C12 H12A 110.7 . . ?
O2 C12 H12B 110.7 . . ?
C11 C12 H12B 110.7 . . ?
H12A C12 H12B 108.8 . . ?
N4 C13 S1 179.2(3) . . ?
N3 C14 S2 177.2(3) . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C16 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O3A C16 C15 127.8(6) . . ?
C15 C16 O3B 111.5(6) . . ?
O3A C16 H16A 105.4 . . ?
C15 C16 H16A 105.4 . . ?
O3A C16 H16B 105.4 . . ?
C15 C16 H16B 105.4 . . ?
H16A C16 H16B 106.0 . . ?

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
O2 H2 O3A 0.873(9) 1.739(12) 2.603(5) 170(2) .
O2 H2 O3B 0.873(9) 1.80(2) 2.604(7) 152(3) .
N2 H2A S2 0.98 2.46 3.405(3) 162.0 1_455
C8 H8A N4 0.97 2.46 2.963(4) 112.2 .

_refine_diff_density_max         0.508
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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 1566998'
_audit_update_record             
;
2017-09-25 deposited with the CCDC.
2017-09-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H28 Co2 N10 O4'
_chemical_formula_sum            'C22 H28 Co2 N10 O4'
_chemical_formula_weight         614.02

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.090(7)
_cell_length_b                   6.708(5)
_cell_length_c                   21.311(16)
_cell_angle_alpha                90
_cell_angle_beta                 97.470(7)
_cell_angle_gamma                90
_cell_volume                     1288.4(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    730
_cell_measurement_theta_min      2.339
_cell_measurement_theta_max      25.627

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            PINK
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_F_000             631.2
_exptl_transmission_factor_min   0.5659
_exptl_transmission_factor_max   0.7453
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    1.338
_shelx_estimated_absorpt_T_min   0.5659
_shelx_estimated_absorpt_T_max   0.5659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Apex II'
_diffrn_measurement_method       'Omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7156
_diffrn_reflns_av_unetI/netI     0.0695
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.339
_diffrn_reflns_theta_max         25.627
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2400
_reflns_number_gt                1470
_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 Apex II'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Mercury 3.8'
_computing_publication_material  'Shelxl 2016/6'
_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)+(0.2000P)²] 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         2400
_refine_ls_number_parameters     159
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1647
_refine_ls_R_factor_gt           0.1150
_refine_ls_wR_factor_ref         0.3673
_refine_ls_wR_factor_gt          0.3295
_refine_ls_goodness_of_fit_ref   1.295
_refine_ls_restrained_S_all      1.297
_refine_ls_shift/su_max          0.045
_refine_ls_shift/su_mean         0.011

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 0.52038(16) 0.47990(19) 0.57027(6) 0.0551(6) Uani 1 1 d . . . . .
O1 O 0.3712(8) 0.6668(10) 0.5780(3) 0.0602(18) Uani 1 1 d . . . . .
O2 O 0.5943(10) 0.6406(14) 0.5053(4) 0.081(2) Uani 1 1 d . . . . .
N1 N 0.4584(13) 0.2947(13) 0.6255(4) 0.076(3) Uani 1 1 d . . . . .
N2 N 0.6727(12) 0.2969(17) 0.5583(5) 0.087(3) Uani 1 1 d . . . . .
H2 H 0.640261 0.214273 0.521130 0.105 Uiso 0.81(3) 1 calc R U P A 1
N3 N 0.6463(10) 0.6146(15) 0.6356(5) 0.067(2) Uani 1 1 d . . . . .
N4 N 0.6231(11) 0.6263(15) 0.6890(4) 0.069(3) Uani 1 1 d . . . . .
N5 N 0.6078(19) 0.649(3) 0.7381(6) 0.143(7) Uani 1 1 d . . . . .
C1 C 0.2697(13) 0.645(2) 0.6178(5) 0.070(3) Uani 1 1 d . . . . .
C2 C 0.1709(15) 0.807(2) 0.6216(6) 0.090(4) Uani 1 1 d . . . . .
H2A H 0.180134 0.920531 0.597161 0.109 Uiso 1 1 calc R U . . .
C3 C 0.063(2) 0.801(4) 0.6600(9) 0.133(8) Uani 1 1 d . . . . .
H3 H 0.002927 0.911843 0.662266 0.160 Uiso 1 1 calc R U . . .
C4 C 0.041(2) 0.637(5) 0.6953(8) 0.134(9) Uani 1 1 d . . . . .
H4 H -0.037954 0.633431 0.719027 0.161 Uiso 1 1 calc R U . . .
C5 C 0.136(2) 0.477(4) 0.6957(7) 0.140(9) Uani 1 1 d . . . . .
H5 H 0.126663 0.367363 0.721750 0.169 Uiso 1 1 calc R U . . .
C6 C 0.2535(16) 0.482(3) 0.6543(6) 0.087(4) Uani 1 1 d . . . . .
C7 C 0.3456(16) 0.318(2) 0.6583(6) 0.083(4) Uani 1 1 d . . . . .
H7 H 0.327276 0.216283 0.686016 0.100 Uiso 1 1 calc R U . . .
C8A C 0.564(3) 0.115(4) 0.6306(13) 0.111(9) Uiso 0.81(3) 1 d . . P A 1
H8AA H 0.576546 0.065070 0.673698 0.133 Uiso 0.81(3) 1 calc R U P A 1
H8AB H 0.521664 0.009464 0.602951 0.133 Uiso 0.81(3) 1 calc R U P A 1
C9A C 0.702(3) 0.169(3) 0.6139(11) 0.117(8) Uiso 0.81(3) 1 d . . P A 1
H9AA H 0.756769 0.051289 0.604207 0.141 Uiso 0.81(3) 1 calc R U P A 1
H9AB H 0.759521 0.239972 0.648386 0.141 Uiso 0.81(3) 1 calc R U P A 1
C10 C 0.8163(15) 0.432(2) 0.5443(7) 0.087(3) Uani 1 1 d D . . . .
H10A H 0.874016 0.361433 0.516214 0.105 Uiso 1 1 calc R U . . .
H10B H 0.879729 0.460139 0.583544 0.105 Uiso 1 1 calc R U . . .
C11 C 0.7500(14) 0.6426(19) 0.5110(5) 0.081(2) Uani 1 1 d D . . . .
H11A H 0.788152 0.755227 0.536624 0.097 Uiso 1 1 calc R U . . .
H11B H 0.781804 0.656432 0.469449 0.097 Uiso 1 1 calc R U . . .
C8B C 0.514(7) 0.117(7) 0.629(2) 0.035(13) Uiso 0.19(3) 1 d . . P A 2
H8BA H 0.433397 0.020697 0.622396 0.043 Uiso 0.19(3) 1 calc R U P A 2
H8BB H 0.566941 0.095864 0.670636 0.043 Uiso 0.19(3) 1 calc R U P A 2
C9B C 0.608(5) 0.086(6) 0.584(2) 0.041(15) Uiso 0.19(3) 1 d . . P A 2
H9BA H 0.555562 0.013512 0.549004 0.049 Uiso 0.19(3) 1 calc R U P A 2
H9BB H 0.690324 0.004716 0.602902 0.049 Uiso 0.19(3) 1 calc R U P A 2


_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 N1 1.849(10) . ?
Co1 O1 1.870(7) . ?
Co1 N2 1.892(11) . ?
Co1 N3 1.910(9) . ?
Co1 O2 1.943(8) . ?
Co1 O2 1.973(8) 3_666 ?
Co1 Co1 2.982(3) 3_666 ?
O1 C1 1.340(12) . ?
O2 C11 1.405(15) . ?
N1 C8B 1.29(5) . ?
N1 C7 1.323(16) . ?
N1 C8A 1.54(3) . ?
N2 C9A 1.46(2) . ?
N2 C10 1.648(18) . ?
N2 C9B 1.66(4) . ?
N2 H2 0.9800 . ?
N3 N4 1.189(13) . ?
N4 N5 1.083(13) . ?
C1 C6 1.366(19) . ?
C1 C2 1.418(17) . ?
C2 C3 1.35(2) . ?
C2 H2A 0.9300 . ?
C3 C4 1.36(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.38(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.47(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.38(2) . ?
C7 H7 0.9300 . ?
C8A C9A 1.39(3) . ?
C8A H8AA 0.9700 . ?
C8A H8AB 0.9700 . ?
C9A H9AA 0.9700 . ?
C9A H9AB 0.9700 . ?
C10 C11 1.658(14) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C8B C9B 1.37(7) . ?
C8B H8BA 0.9700 . ?
C8B H8BB 0.9700 . ?
C9B H9BA 0.9700 . ?
C9B H9BB 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Co1 O1 96.3(4) . . ?
N1 Co1 N2 86.5(5) . . ?
O1 Co1 N2 177.0(4) . . ?
N1 Co1 N3 93.3(4) . . ?
O1 Co1 N3 89.5(4) . . ?
N2 Co1 N3 91.5(5) . . ?
N1 Co1 O2 171.5(4) . . ?
O1 Co1 O2 90.7(3) . . ?
N2 Co1 O2 86.4(5) . . ?
N3 Co1 O2 91.5(4) . . ?
N1 Co1 O2 94.1(4) . 3_666 ?
O1 Co1 O2 91.9(4) . 3_666 ?
N2 Co1 O2 86.7(4) . 3_666 ?
N3 Co1 O2 172.2(4) . 3_666 ?
O2 Co1 O2 80.8(4) . 3_666 ?
N1 Co1 Co1 133.8(3) . 3_666 ?
O1 Co1 Co1 91.7(2) . 3_666 ?
N2 Co1 Co1 85.5(4) . 3_666 ?
N3 Co1 Co1 132.3(3) . 3_666 ?
O2 Co1 Co1 40.8(2) . 3_666 ?
O2 Co1 Co1 40.0(2) 3_666 3_666 ?
C1 O1 Co1 123.4(7) . . ?
C11 O2 Co1 112.4(7) . . ?
C11 O2 Co1 119.6(7) . 3_666 ?
Co1 O2 Co1 99.2(4) . 3_666 ?
C8B N1 C7 114(3) . . ?
C7 N1 C8A 125.1(14) . . ?
C8B N1 Co1 120(2) . . ?
C7 N1 Co1 125.4(10) . . ?
C8A N1 Co1 109.4(12) . . ?
C9A N2 C10 113.9(13) . . ?
C10 N2 C9B 148.9(18) . . ?
C9A N2 Co1 109.3(11) . . ?
C10 N2 Co1 106.1(7) . . ?
C9B N2 Co1 102.1(16) . . ?
C9A N2 H2 109.1 . . ?
C10 N2 H2 109.1 . . ?
Co1 N2 H2 109.1 . . ?
N4 N3 Co1 124.4(8) . . ?
N5 N4 N3 175.0(14) . . ?
O1 C1 C6 125.5(12) . . ?
O1 C1 C2 116.6(11) . . ?
C6 C1 C2 117.9(12) . . ?
C3 C2 C1 121.5(17) . . ?
C3 C2 H2A 119.3 . . ?
C1 C2 H2A 119.3 . . ?
C2 C3 C4 122.1(19) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 119.0 . . ?
C3 C4 C5 119.5(19) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 119(2) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C1 C6 C7 124.6(12) . . ?
C1 C6 C5 120.0(18) . . ?
C7 C6 C5 115.2(16) . . ?
N1 C7 C6 124.5(12) . . ?
N1 C7 H7 117.8 . . ?
C6 C7 H7 117.8 . . ?
C9A C8A N1 111(2) . . ?
C9A C8A H8AA 109.5 . . ?
N1 C8A H8AA 109.5 . . ?
C9A C8A H8AB 109.5 . . ?
N1 C8A H8AB 109.5 . . ?
H8AA C8A H8AB 108.1 . . ?
C8A C9A N2 106.6(19) . . ?
C8A C9A H9AA 110.4 . . ?
N2 C9A H9AA 110.4 . . ?
C8A C9A H9AB 110.4 . . ?
N2 C9A H9AB 110.4 . . ?
H9AA C9A H9AB 108.6 . . ?
N2 C10 C11 107.1(9) . . ?
N2 C10 H10A 110.3 . . ?
C11 C10 H10A 110.3 . . ?
N2 C10 H10B 110.3 . . ?
C11 C10 H10B 110.3 . . ?
H10A C10 H10B 108.6 . . ?
O2 C11 C10 109.6(10) . . ?
O2 C11 H11A 109.8 . . ?
C10 C11 H11A 109.8 . . ?
O2 C11 H11B 109.8 . . ?
C10 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?
N1 C8B C9B 112(4) . . ?
N1 C8B H8BA 109.2 . . ?
C9B C8B H8BA 109.2 . . ?
N1 C8B H8BB 109.2 . . ?
C9B C8B H8BB 109.2 . . ?
H8BA C8B H8BB 107.9 . . ?
C8B C9B N2 113(3) . . ?
C8B C9B H9BA 109.0 . . ?
N2 C9B H9BA 109.0 . . ?
C8B C9B H9BB 109.1 . . ?
N2 C9B H9BB 109.1 . . ?
H9BA C9B H9BB 107.8 . . ?

_refine_diff_density_max         1.532
_refine_diff_density_min         -1.194
_refine_diff_density_rms         0.175

#
_vrf_PLAT084_2                   
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.37 Report
RESPONSE: The crystal was poorly diffracting at higher Bragg angles.
;
#
#
_vrf_PLAT201_2                   
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          3 Report
RESPONSE: We did not refine the disordered carbon atoms(C8, C9)
anisotropically.
;
#
_vrf_PLAT341_2                   
;
PROBLEM:  Low Bond Precision on  C-C Bonds ...............      0.02114 Ang.
RESPONSE: Weakly diffracting crystal resulting in relatively high
Rint and poor data to parameter ratio, appears to be responsible for low
bond precision of c-c bond.
;
# end Validation Reply Form

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4
_database_code_depnum_ccdc_archive 'CCDC 1567000'
_audit_update_record             
;
2017-09-05 deposited with the CCDC.
2017-09-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H17 Co N8 O2'
_chemical_formula_sum            'C12 H17 Co N8 O2'
_chemical_formula_weight         364.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.345(4)
_cell_length_b                   9.546(5)
_cell_length_c                   10.597(5)
_cell_angle_alpha                71.366(7)
_cell_angle_beta                 67.949(7)
_cell_angle_gamma                87.576(7)
_cell_volume                     738.5(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    625
_cell_measurement_theta_min      0.6235
_cell_measurement_theta_max      0.7453

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   0.6235
_exptl_transmission_factor_max   0.7453
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    1.186
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_absorpt_special_details   SADABS
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Apex II'
_diffrn_measurement_method       'Omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5570
_diffrn_reflns_av_unetI/netI     0.1038
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.195
_diffrn_reflns_theta_max         26.033
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             2780
_reflns_number_gt                1471
_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 Apex II'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Mercury 3.8'
_computing_publication_material  'Shelxl 2016/6'
_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)+(0.0330P)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         2780
_refine_ls_number_parameters     211
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1134
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1066
_refine_ls_wR_factor_gt          0.0891
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_restrained_S_all      0.959
_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 0.46342(8) 0.38327(7) 0.83267(7) 0.0472(2) Uani 1 1 d D . . . .
O1 O 0.6095(4) 0.5452(3) 0.8021(3) 0.0479(8) Uani 1 1 d . . . . .
O2 O 0.2998(4) 0.4356(3) 0.9932(3) 0.0510(9) Uani 1 1 d D . . . .
H2 H 0.316(3) 0.449(4) 1.065(2) 0.076 Uiso 1 1 d D U . . .
N1 N 0.6258(5) 0.3350(4) 0.6756(4) 0.0473(11) Uani 1 1 d . . . . .
N2 N 0.2828(5) 0.2275(4) 0.8822(5) 0.0569(12) Uani 1 1 d . . . . .
H2A H 0.211784 0.273255 0.826870 0.068 Uiso 1 1 calc R U . . .
N3 N 0.3532(5) 0.5065(5) 0.7095(4) 0.0557(12) Uani 1 1 d . . . . .
N4 N 0.3204(5) 0.6297(5) 0.7146(4) 0.0519(11) Uani 1 1 d . . . . .
N5 N 0.2832(6) 0.7480(5) 0.7129(5) 0.0836(16) Uani 1 1 d . . . . .
N6 N 0.5563(5) 0.2487(4) 0.9639(4) 0.0549(12) Uani 1 1 d . . . . .
N7 N 0.7095(6) 0.2598(4) 0.9357(4) 0.0523(11) Uani 1 1 d . . . . .
N8 N 0.8540(6) 0.2643(5) 0.9145(5) 0.0760(15) Uani 1 1 d . . . . .
C1 C 0.7001(6) 0.6355(5) 0.6703(6) 0.0441(12) Uani 1 1 d . . . . .
C2 C 0.7316(6) 0.7866(5) 0.6469(6) 0.0544(14) Uani 1 1 d . . . . .
H2B H 0.683556 0.824684 0.722358 0.065 Uiso 1 1 calc R U . . .
C3 C 0.8338(7) 0.8781(6) 0.5118(7) 0.0614(15) Uani 1 1 d . . . . .
H3 H 0.851032 0.978598 0.497257 0.074 Uiso 1 1 calc R U . . .
C4 C 0.9115(6) 0.8274(6) 0.3976(6) 0.0632(16) Uani 1 1 d . . . . .
H4 H 0.983323 0.891163 0.308074 0.076 Uiso 1 1 calc R U . . .
C5 C 0.8803(6) 0.6798(6) 0.4192(5) 0.0548(14) Uani 1 1 d . . . . .
H5 H 0.932727 0.643289 0.343114 0.066 Uiso 1 1 calc R U . . .
C6 C 0.7713(6) 0.5833(5) 0.5530(6) 0.0459(12) Uani 1 1 d . . . . .
C7 C 0.7407(7) 0.4298(6) 0.5689(6) 0.0520(13) Uani 1 1 d . . . . .
H7 H 0.811472 0.397066 0.494228 0.062 Uiso 1 1 calc R U . . .
C8 C 0.6282(7) 0.1821(5) 0.6722(6) 0.0660(16) Uani 1 1 d . . . . .
H8A H 0.668980 0.120446 0.744555 0.079 Uiso 1 1 calc R U . . .
H8B H 0.709426 0.181124 0.578728 0.079 Uiso 1 1 calc R U . . .
C9 C 0.4518(7) 0.1171(6) 0.6995(7) 0.0742(18) Uani 1 1 d . . . . .
H9A H 0.404664 0.184942 0.634864 0.089 Uiso 1 1 calc R U . . .
H9B H 0.464279 0.024614 0.678324 0.089 Uiso 1 1 calc R U . . .
C10 C 0.3272(8) 0.0883(5) 0.8524(7) 0.0742(18) Uani 1 1 d . . . . .
H10A H 0.222348 0.032761 0.869146 0.089 Uiso 1 1 calc R U . . .
H10B H 0.379056 0.028868 0.917651 0.089 Uiso 1 1 calc R U . . .
C11 C 0.1684(7) 0.1993(6) 1.0351(6) 0.0664(16) Uani 1 1 d . . . . .
H11A H 0.224003 0.140019 1.097355 0.080 Uiso 1 1 calc R U . . .
H11B H 0.059964 0.145430 1.057169 0.080 Uiso 1 1 calc R U . . .
C12 C 0.1342(6) 0.3454(6) 1.0592(6) 0.0681(16) Uani 1 1 d D . . . .
H12A H 0.054370 0.394446 1.015832 0.082 Uiso 1 1 calc R U . . .
H12B H 0.082950 0.330942 1.161633 0.082 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O1 1.877(3) . ?
Co1 N1 1.887(4) . ?
Co1 O2 1.937(3) . ?
Co1 N3 1.939(4) . ?
Co1 N6 1.942(4) . ?
Co1 N2 1.964(4) . ?
O1 C1 1.326(5) . ?
O2 C12 1.460(5) . ?
O2 H2 0.872(9) . ?
N1 C7 1.274(6) . ?
N1 C8 1.471(5) . ?
N2 C10 1.463(6) . ?
N2 C11 1.480(6) . ?
N2 H2A 0.9800 . ?
N3 N4 1.210(5) . ?
N4 N5 1.155(5) . ?
N6 N7 1.200(5) . ?
N7 N8 1.141(5) . ?
C1 C6 1.400(6) . ?
C1 C2 1.402(6) . ?
C2 C3 1.374(6) . ?
C2 H2B 0.9300 . ?
C3 C4 1.370(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.398(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.443(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.510(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.503(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.494(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Co1 N1 92.53(16) . . ?
O1 Co1 O2 86.42(13) . . ?
N1 Co1 O2 178.95(16) . . ?
O1 Co1 N3 92.05(15) . . ?
N1 Co1 N3 90.83(17) . . ?
O2 Co1 N3 89.26(16) . . ?
O1 Co1 N6 92.29(15) . . ?
N1 Co1 N6 90.94(17) . . ?
O2 Co1 N6 89.04(16) . . ?
N3 Co1 N6 175.23(17) . . ?
O1 Co1 N2 171.44(17) . . ?
N1 Co1 N2 95.64(18) . . ?
O2 Co1 N2 85.40(16) . . ?
N3 Co1 N2 85.33(17) . . ?
N6 Co1 N2 90.09(16) . . ?
C1 O1 Co1 121.2(3) . . ?
C12 O2 Co1 112.2(3) . . ?
C12 O2 H2 104.6(16) . . ?
Co1 O2 H2 128.7(18) . . ?
C7 N1 C8 116.1(4) . . ?
C7 N1 Co1 123.0(4) . . ?
C8 N1 Co1 120.9(3) . . ?
C10 N2 C11 111.1(4) . . ?
C10 N2 Co1 121.3(3) . . ?
C11 N2 Co1 106.9(3) . . ?
C10 N2 H2A 105.4 . . ?
C11 N2 H2A 105.4 . . ?
Co1 N2 H2A 105.4 . . ?
N4 N3 Co1 119.4(3) . . ?
N5 N4 N3 175.1(5) . . ?
N7 N6 Co1 118.8(3) . . ?
N8 N7 N6 176.7(5) . . ?
O1 C1 C6 121.7(4) . . ?
O1 C1 C2 119.8(5) . . ?
C6 C1 C2 118.4(5) . . ?
C3 C2 C1 119.6(5) . . ?
C3 C2 H2B 120.2 . . ?
C1 C2 H2B 120.2 . . ?
C4 C3 C2 122.7(5) . . ?
C4 C3 H3 118.7 . . ?
C2 C3 H3 118.7 . . ?
C3 C4 C5 118.1(5) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C4 C5 C6 121.4(5) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 119.6(5) . . ?
C5 C6 C7 119.1(5) . . ?
C1 C6 C7 121.3(5) . . ?
N1 C7 C6 126.1(5) . . ?
N1 C7 H7 116.9 . . ?
C6 C7 H7 116.9 . . ?
N1 C8 C9 112.5(4) . . ?
N1 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
N1 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
C10 C9 C8 112.3(5) . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
N2 C10 C9 111.1(4) . . ?
N2 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
N2 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
N2 C11 C12 108.3(4) . . ?
N2 C11 H11A 110.0 . . ?
C12 C11 H11A 110.0 . . ?
N2 C11 H11B 110.0 . . ?
C12 C11 H11B 110.0 . . ?
H11A C11 H11B 108.4 . . ?
O2 C12 C11 107.8(4) . . ?
O2 C12 H12A 110.1 . . ?
C11 C12 H12A 110.1 . . ?
O2 C12 H12B 110.1 . . ?
C11 C12 H12B 110.1 . . ?
H12A C12 H12B 108.5 . . ?

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
O2 H2 O1 0.872(9) 1.752(14) 2.610(4) 167(3) 2_667
C10 H10B N6 0.97 2.67 3.498(6) 143.1 2_657
C10 H10B N7 0.97 2.67 3.314(6) 124.2 2_657
C11 H11B N8 0.97 2.69 3.282(7) 120.1 1_455

_refine_diff_density_max         0.376
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.076

