# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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 1510109'
_audit_update_record             
;
2016-10-16 deposited with the CCDC.
2016-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H12 Co N4 O8'
_chemical_formula_weight         519.29

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'
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           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                   19.8858(9)
_cell_length_b                   11.4146(5)
_cell_length_c                   9.5384(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.344(2)
_cell_angle_gamma                90
_cell_volume                     2055.08(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8009
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      28.30

_exptl_crystal_description       rod
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_F_000             1052
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.897
_shelx_estimated_absorpt_T_min   0.787
_shelx_estimated_absorpt_T_max   0.900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.761
_exptl_absorpt_correction_T_max  0.892
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13645
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.085
_diffrn_reflns_theta_max         28.311
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2531
_reflns_number_gt                2282
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0505P)²+2.5674P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2531
_refine_ls_number_parameters     161
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0853
_refine_ls_wR_factor_gt          0.0822
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 0.0000 -0.04153(2) 0.2500 0.01223(10) Uani 1 2 d S T P . .
C1 C 0.10001(8) -0.03346(12) 0.05439(17) 0.0143(3) Uani 1 1 d . . . . .
C2 C 0.16030(8) -0.09917(13) 0.02484(16) 0.0170(3) Uani 1 1 d . . . . .
C3 C 0.19597(9) -0.04769(13) -0.06593(18) 0.0192(3) Uani 1 1 d . . . . .
H3A H 0.1852 0.0282 -0.1014 0.023 Uiso 1 1 calc R U . . .
C4 C 0.17877(8) -0.20892(14) 0.08189(17) 0.0186(3) Uani 1 1 d . . . . .
H4A H 0.1558 -0.2414 0.1438 0.022 Uiso 1 1 calc R U . . .
C5 C 0.24656(8) -0.11127(14) -0.10086(18) 0.0198(3) Uani 1 1 d . . . . .
C6 C 0.23257(8) -0.27401(14) 0.04798(17) 0.0182(3) Uani 1 1 d . . . . .
C7 C 0.05052(8) 0.21027(14) 0.21752(19) 0.0208(3) Uani 1 1 d . . . . .
H7A H 0.0858 0.1694 0.1932 0.025 Uiso 1 1 calc R U . . .
C8 C 0.05311(9) 0.33148(13) 0.2183(2) 0.0228(3) Uani 1 1 d . . . . .
H8A H 0.0901 0.3702 0.1977 0.027 Uiso 1 1 calc R U . . .
C9 C 0.0000 0.39474(18) 0.2500 0.0181(4) Uani 1 2 d S T P . .
C10 C 0.0000 0.52450(18) 0.2500 0.0187(4) Uani 1 2 d S T P . .
C11 C -0.06073(9) 0.58744(14) 0.17677(19) 0.0229(3) Uani 1 1 d . . . . .
H11A H -0.1025 0.5485 0.1270 0.027 Uiso 1 1 calc R U . . .
C12 C -0.05831(9) 0.70894(13) 0.17866(19) 0.0215(3) Uani 1 1 d . . . . .
H12A H -0.0991 0.7500 0.1280 0.026 Uiso 1 1 calc R U . . .
N1 N 0.27887(8) -0.05671(13) -0.20396(18) 0.0273(3) Uani 1 1 d . . . . .
N2 N 0.0000 0.14864(15) 0.2500 0.0155(3) Uani 1 2 d S T P . .
N3 N 0.0000 0.77009(15) 0.2500 0.0163(4) Uani 1 2 d S T P . .
O1 O 0.08632(6) -0.06082(9) 0.16980(12) 0.0171(2) Uani 1 1 d . . . . .
O2 O 0.06993(6) 0.04481(9) -0.03609(12) 0.0163(2) Uani 1 1 d . . . . .
O3 O 0.27995(9) -0.11299(14) -0.31253(16) 0.0423(4) Uani 1 1 d . . . . .
O4 O 0.29992(9) 0.04379(13) -0.1782(2) 0.0430(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 O2 2.0766(11) 6_556 ?
Co1 O2 2.0766(11) 5 ?
Co1 O1 2.0992(11) . ?
Co1 O1 2.0992(11) 2 ?
Co1 N3 2.1502(17) 1_545 ?
Co1 N2 2.1707(17) . ?
C1 O1 1.2539(19) . ?
C1 O2 1.2553(18) . ?
C1 C2 1.5141(19) . ?
C2 C4 1.369(2) . ?
C2 C3 1.409(2) . ?
C3 C5 1.364(2) . ?
C3 H3A 0.9300 . ?
C4 C6 1.421(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.418(2) 7_545 ?
C5 N1 1.472(2) . ?
C6 C5 1.418(2) 7_545 ?
C6 C6 1.420(3) 7_545 ?
C7 N2 1.3402(17) . ?
C7 C8 1.384(2) . ?
C7 H7A 0.9300 . ?
C8 C9 1.3893(19) . ?
C8 H8A 0.9300 . ?
C9 C8 1.3892(19) 2 ?
C9 C10 1.481(3) . ?
C10 C11 1.390(2) . ?
C10 C11 1.390(2) 2 ?
C11 C12 1.388(2) . ?
C11 H11A 0.9300 . ?
C12 N3 1.3409(19) . ?
C12 H12A 0.9300 . ?
N1 O4 1.219(2) . ?
N1 O3 1.225(2) . ?
N2 C7 1.3402(17) 2 ?
N3 C12 1.3409(19) 2 ?
N3 Co1 2.1503(17) 1_565 ?
O2 Co1 2.0766(11) 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
O2 Co1 O2 177.93(6) 6_556 5 ?
O2 Co1 O1 89.12(4) 6_556 . ?
O2 Co1 O1 90.67(4) 5 . ?
O2 Co1 O1 90.67(4) 6_556 2 ?
O2 Co1 O1 89.12(4) 5 2 ?
O1 Co1 O1 167.96(6) . 2 ?
O2 Co1 N3 88.97(3) 6_556 1_545 ?
O2 Co1 N3 88.97(3) 5 1_545 ?
O1 Co1 N3 83.98(3) . 1_545 ?
O1 Co1 N3 83.98(3) 2 1_545 ?
O2 Co1 N2 91.03(3) 6_556 . ?
O2 Co1 N2 91.03(3) 5 . ?
O1 Co1 N2 96.02(3) . . ?
O1 Co1 N2 96.02(3) 2 . ?
N3 Co1 N2 180.0 1_545 . ?
O1 C1 O2 126.35(14) . . ?
O1 C1 C2 116.33(13) . . ?
O2 C1 C2 117.29(13) . . ?
C4 C2 C3 120.13(13) . . ?
C4 C2 C1 120.55(13) . . ?
C3 C2 C1 119.29(13) . . ?
C5 C3 C2 118.74(14) . . ?
C5 C3 H3A 120.6 . . ?
C2 C3 H3A 120.6 . . ?
C2 C4 C6 120.99(14) . . ?
C2 C4 H4A 119.5 . . ?
C6 C4 H4A 119.5 . . ?
C3 C5 C6 124.08(14) . 7_545 ?
C3 C5 N1 116.66(14) . . ?
C6 C5 N1 119.22(13) 7_545 . ?
C5 C6 C6 115.99(17) 7_545 7_545 ?
C5 C6 C4 123.99(14) 7_545 . ?
C6 C6 C4 119.99(18) 7_545 . ?
N2 C7 C8 123.56(14) . . ?
N2 C7 H7A 118.2 . . ?
C8 C7 H7A 118.2 . . ?
C7 C8 C9 119.40(15) . . ?
C7 C8 H8A 120.3 . . ?
C9 C8 H8A 120.3 . . ?
C8 C9 C8 117.36(19) 2 . ?
C8 C9 C10 121.32(10) 2 . ?
C8 C9 C10 121.32(10) . . ?
C11 C10 C11 117.8(2) . 2 ?
C11 C10 C9 121.12(10) . . ?
C11 C10 C9 121.12(10) 2 . ?
C12 C11 C10 119.27(15) . . ?
C12 C11 H11A 120.4 . . ?
C10 C11 H11A 120.4 . . ?
N3 C12 C11 123.22(15) . . ?
N3 C12 H12A 118.4 . . ?
C11 C12 H12A 118.4 . . ?
O4 N1 O3 124.59(17) . . ?
O4 N1 C5 117.25(16) . . ?
O3 N1 C5 118.08(16) . . ?
C7 N2 C7 116.68(18) 2 . ?
C7 N2 Co1 121.66(9) 2 . ?
C7 N2 Co1 121.66(9) . . ?
C12 N3 C12 117.26(18) . 2 ?
C12 N3 Co1 121.37(9) . 1_565 ?
C12 N3 Co1 121.37(9) 2 1_565 ?
C1 O1 Co1 136.24(10) . . ?
C1 O2 Co1 133.59(10) . 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
O1 C1 C2 C4 25.4(2) . . . . ?
O2 C1 C2 C4 -156.45(15) . . . . ?
O1 C1 C2 C3 -156.51(14) . . . . ?
O2 C1 C2 C3 21.6(2) . . . . ?
C4 C2 C3 C5 3.0(2) . . . . ?
C1 C2 C3 C5 -175.09(14) . . . . ?
C3 C2 C4 C6 -1.7(2) . . . . ?
C1 C2 C4 C6 176.40(14) . . . . ?
C2 C3 C5 C6 -1.9(3) . . . 7_545 ?
C2 C3 C5 N1 176.00(15) . . . . ?
C2 C4 C6 C5 -178.79(15) . . . 7_545 ?
C2 C4 C6 C6 -0.8(3) . . . 7_545 ?
N2 C7 C8 C9 -1.9(3) . . . . ?
C7 C8 C9 C8 0.87(12) . . . 2 ?
C7 C8 C9 C10 -179.13(12) . . . . ?
C8 C9 C10 C11 -47.88(12) 2 . . . ?
C8 C9 C10 C11 132.12(12) . . . . ?
C8 C9 C10 C11 132.12(12) 2 . . 2 ?
C8 C9 C10 C11 -47.88(12) . . . 2 ?
C11 C10 C11 C12 0.45(11) 2 . . . ?
C9 C10 C11 C12 -179.55(11) . . . . ?
C10 C11 C12 N3 -1.0(2) . . . . ?
C3 C5 N1 O4 48.9(2) . . . . ?
C6 C5 N1 O4 -133.11(17) 7_545 . . . ?
C3 C5 N1 O3 -127.96(17) . . . . ?
C6 C5 N1 O3 50.0(2) 7_545 . . . ?
C8 C7 N2 C7 0.95(13) . . . 2 ?
C8 C7 N2 Co1 -179.05(13) . . . . ?
C11 C12 N3 C12 0.49(12) . . . 2 ?
C11 C12 N3 Co1 -179.51(12) . . . 1_565 ?
O2 C1 O1 Co1 21.2(2) . . . . ?
C2 C1 O1 Co1 -160.89(10) . . . . ?
O1 C1 O2 Co1 -108.61(16) . . . 5 ?
C2 C1 O2 Co1 73.46(18) . . . 5 ?

_refine_diff_density_max         0.672
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.076

_shelxl_version_number           2014-3


_exptl_crystal_preparation       ', Magnetic properties'
####################################################################### 
# 
# 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 1510110'
_audit_update_record             
;
2016-10-16 deposited with the CCDC.
2016-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H12 Co N4 O8'
_chemical_formula_weight         543.31

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           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                   22.3802(6)
_cell_length_b                   10.2363(3)
_cell_length_c                   8.9794(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.4600(10)
_cell_angle_gamma                90
_cell_volume                     2034.71(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9744
_cell_measurement_theta_min      2.192
_cell_measurement_theta_max      28.267

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_F_000             1100
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.911
_shelx_estimated_absorpt_T_min   0.772
_shelx_estimated_absorpt_T_max   0.914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.752
_exptl_absorpt_correction_T_max  0.889
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13498
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.840
_diffrn_reflns_theta_max         28.286
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2503
_reflns_number_gt                2390
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0746P)²+12.2772P] 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         2503
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1518
_refine_ls_wR_factor_gt          0.1499
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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 0.0000 0.07599(5) 0.7500 0.01954(18) Uani 1 2 d S T P . .
C1 C 0.08349(11) 0.0954(3) 0.4964(3) 0.0201(5) Uani 1 1 d . . . . .
C2 C 0.14621(12) 0.1464(3) 0.4800(4) 0.0284(6) Uani 1 1 d . . . . .
C3 C 0.17000(14) 0.1119(3) 0.3448(4) 0.0328(7) Uani 1 1 d . . . . .
H3A H 0.1471 0.0633 0.2695 0.039 Uiso 1 1 calc R U . . .
C4 C 0.22696(15) 0.1520(3) 0.3292(4) 0.0311(6) Uani 1 1 d . . . . .
C5 C 0.26160(15) 0.2315(3) 0.4341(3) 0.0295(6) Uani 1 1 d . . . . .
C6 C 0.17920(14) 0.2188(3) 0.5858(4) 0.0321(7) Uani 1 1 d . . . . .
H6A H 0.1639 0.2378 0.6742 0.039 Uiso 1 1 calc R U . . .
C7 C -0.08770(17) 0.2394(3) 0.5134(4) 0.0396(8) Uani 1 1 d . . . . .
H7A H -0.1007 0.1594 0.4714 0.048 Uiso 1 1 calc R U . . .
C8 C -0.11580(19) 0.3529(4) 0.4523(5) 0.0465(9) Uani 1 1 d . . . . .
H8A H -0.1476 0.3480 0.3732 0.056 Uiso 1 1 calc R U . . .
C9 C -0.09606(18) 0.4705(4) 0.5097(5) 0.0445(9) Uani 1 1 d . . . . .
H9A H -0.1143 0.5470 0.4696 0.053 Uiso 1 1 calc R U . . .
C10 C -0.04820(16) 0.4770(3) 0.6293(4) 0.0353(7) Uani 1 1 d . . . . .
C11 C -0.02389(14) 0.3574(3) 0.6870(3) 0.0271(6) Uani 1 1 d . . . . .
C12 C -0.0235(2) 0.5962(3) 0.6934(5) 0.0461(9) Uani 1 1 d . . . . .
H12A H -0.0399 0.6753 0.6565 0.055 Uiso 1 1 calc R U . . .
N1 N 0.25335(13) 0.1051(3) 0.1957(3) 0.0333(6) Uani 1 1 d . . . . .
N2 N -0.04313(12) 0.2402(3) 0.6289(3) 0.0286(5) Uani 1 1 d . . . . .
O1 O 0.07190(10) 0.0861(2) 0.6269(3) 0.0320(5) Uani 1 1 d . . . . .
O2 O 0.05083(10) 0.0673(2) 0.3766(3) 0.0300(5) Uani 1 1 d . . . . .
O3 O 0.29957(15) 0.0445(4) 0.2127(4) 0.0663(10) Uani 1 1 d . . . . .
O4 O 0.22173(16) 0.1194(5) 0.0777(3) 0.0691(10) 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 2.084(2) 2_556 ?
Co1 O1 2.084(2) . ?
Co1 O2 2.087(2) 5_556 ?
Co1 O2 2.087(2) 6_556 ?
Co1 N2 2.152(3) 2_556 ?
Co1 N2 2.152(3) . ?
C1 O1 1.241(4) . ?
C1 O2 1.242(4) . ?
C1 C2 1.525(4) . ?
C2 C6 1.338(4) . ?
C2 C3 1.440(5) . ?
C3 C4 1.366(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.391(4) . ?
C4 N1 1.492(4) . ?
C5 C5 1.412(6) 7_556 ?
C5 C6 1.455(5) 7_556 ?
C6 C5 1.454(5) 7_556 ?
C6 H6A 0.9300 . ?
C7 N2 1.329(4) . ?
C7 C8 1.394(5) . ?
C7 H7A 0.9300 . ?
C8 C9 1.358(6) . ?
C8 H8A 0.9300 . ?
C9 C10 1.402(5) . ?
C9 H9A 0.9300 . ?
C10 C11 1.407(4) . ?
C10 C12 1.426(5) . ?
C11 N2 1.353(4) . ?
C11 C11 1.437(6) 2_556 ?
C12 C12 1.350(9) 2_556 ?
C12 H12A 0.9300 . ?
N1 O4 1.193(4) . ?
N1 O3 1.196(4) . ?
O2 Co1 2.087(2) 5_556 ?

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 174.32(14) 2_556 . ?
O1 Co1 O2 85.53(9) 2_556 5_556 ?
O1 Co1 O2 98.48(9) . 5_556 ?
O1 Co1 O2 98.48(9) 2_556 6_556 ?
O1 Co1 O2 85.53(9) . 6_556 ?
O2 Co1 O2 90.71(13) 5_556 6_556 ?
O1 Co1 N2 90.99(10) 2_556 2_556 ?
O1 Co1 N2 84.56(10) . 2_556 ?
O2 Co1 N2 172.77(9) 5_556 2_556 ?
O2 Co1 N2 96.08(10) 6_556 2_556 ?
O1 Co1 N2 84.56(10) 2_556 . ?
O1 Co1 N2 90.99(10) . . ?
O2 Co1 N2 96.08(10) 5_556 . ?
O2 Co1 N2 172.77(10) 6_556 . ?
N2 Co1 N2 77.25(14) 2_556 . ?
O1 C1 O2 128.5(3) . . ?
O1 C1 C2 116.2(3) . . ?
O2 C1 C2 115.4(3) . . ?
C6 C2 C3 120.1(3) . . ?
C6 C2 C1 122.7(3) . . ?
C3 C2 C1 117.2(3) . . ?
C4 C3 C2 118.6(3) . . ?
C4 C3 H3A 120.7 . . ?
C2 C3 H3A 120.7 . . ?
C3 C4 C5 122.9(3) . . ?
C3 C4 N1 118.1(3) . . ?
C5 C4 N1 119.0(3) . . ?
C4 C5 C5 119.1(4) . 7_556 ?
C4 C5 C6 123.3(3) . 7_556 ?
C5 C5 C6 117.6(4) 7_556 7_556 ?
C2 C6 C5 121.6(3) . 7_556 ?
C2 C6 H6A 119.2 . . ?
C5 C6 H6A 119.2 7_556 . ?
N2 C7 C8 123.0(3) . . ?
N2 C7 H7A 118.5 . . ?
C8 C7 H7A 118.5 . . ?
C9 C8 C7 119.1(3) . . ?
C9 C8 H8A 120.4 . . ?
C7 C8 H8A 120.4 . . ?
C8 C9 C10 120.1(3) . . ?
C8 C9 H9A 119.9 . . ?
C10 C9 H9A 119.9 . . ?
C9 C10 C11 116.8(3) . . ?
C9 C10 C12 123.9(3) . . ?
C11 C10 C12 119.3(3) . . ?
N2 C11 C10 123.0(3) . . ?
N2 C11 C11 117.45(16) . 2_556 ?
C10 C11 C11 119.5(2) . 2_556 ?
C12 C12 C10 121.1(2) 2_556 . ?
C12 C12 H12A 119.4 2_556 . ?
C10 C12 H12A 119.4 . . ?
O4 N1 O3 124.5(3) . . ?
O4 N1 C4 114.9(3) . . ?
O3 N1 C4 120.1(3) . . ?
C7 N2 C11 117.8(3) . . ?
C7 N2 Co1 128.2(2) . . ?
C11 N2 Co1 113.85(19) . . ?
C1 O1 Co1 142.1(2) . . ?
C1 O2 Co1 147.0(2) . 5_556 ?

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
O1 C1 C2 C6 -22.8(4) . . . . ?
O2 C1 C2 C6 157.9(3) . . . . ?
O1 C1 C2 C3 156.3(3) . . . . ?
O2 C1 C2 C3 -23.0(4) . . . . ?
C6 C2 C3 C4 1.5(5) . . . . ?
C1 C2 C3 C4 -177.6(3) . . . . ?
C2 C3 C4 C5 -4.1(5) . . . . ?
C2 C3 C4 N1 174.3(3) . . . . ?
C3 C4 C5 C5 2.8(6) . . . 7_556 ?
N1 C4 C5 C5 -175.6(4) . . . 7_556 ?
C3 C4 C5 C6 -176.2(3) . . . 7_556 ?
N1 C4 C5 C6 5.5(5) . . . 7_556 ?
C3 C2 C6 C5 2.3(5) . . . 7_556 ?
C1 C2 C6 C5 -178.7(3) . . . 7_556 ?
N2 C7 C8 C9 1.9(7) . . . . ?
C7 C8 C9 C10 -0.3(6) . . . . ?
C8 C9 C10 C11 -1.7(6) . . . . ?
C8 C9 C10 C12 178.1(4) . . . . ?
C9 C10 C11 N2 2.5(5) . . . . ?
C12 C10 C11 N2 -177.3(3) . . . . ?
C9 C10 C11 C11 -177.9(4) . . . 2_556 ?
C12 C10 C11 C11 2.3(6) . . . 2_556 ?
C9 C10 C12 C12 -178.7(5) . . . 2_556 ?
C11 C10 C12 C12 1.1(7) . . . 2_556 ?
C3 C4 N1 O4 50.3(5) . . . . ?
C5 C4 N1 O4 -131.3(4) . . . . ?
C3 C4 N1 O3 -121.4(4) . . . . ?
C5 C4 N1 O3 57.1(5) . . . . ?
C8 C7 N2 C11 -1.2(6) . . . . ?
C8 C7 N2 Co1 174.1(3) . . . . ?
C10 C11 N2 C7 -1.0(5) . . . . ?
C11 C11 N2 C7 179.4(4) 2_556 . . . ?
C10 C11 N2 Co1 -177.0(2) . . . . ?
C11 C11 N2 Co1 3.4(4) 2_556 . . . ?
O2 C1 O1 Co1 -22.0(5) . . . . ?
C2 C1 O1 Co1 158.8(2) . . . . ?
O1 C1 O2 Co1 -56.7(5) . . . 5_556 ?
C2 C1 O2 Co1 122.5(3) . . . 5_556 ?

_refine_diff_density_max         1.771
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.100

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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 1510111'
_audit_update_record             
;
2016-10-16 deposited with the CCDC.
2016-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H14 Co N4 O8'
_chemical_formula_weight         545.32

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'
Co Co 0.3494 0.9721 '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           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                   17.7867(10)
_cell_length_b                   13.6324(7)
_cell_length_c                   9.8647(5)
_cell_angle_alpha                90
_cell_angle_beta                 116.2020(10)
_cell_angle_gamma                90
_cell_volume                     2146.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8989
_cell_measurement_theta_min      2.503
_cell_measurement_theta_max      28.261

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_F_000             1108
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.864
_shelx_estimated_absorpt_T_min   0.782
_shelx_estimated_absorpt_T_max   0.846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.756
_exptl_absorpt_correction_T_max  0.909
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14294
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.965
_diffrn_reflns_theta_max         28.302
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2598
_reflns_number_gt                2397
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0519P)²+1.7109P] 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         2598
_refine_ls_number_parameters     242
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0811
_refine_ls_wR_factor_gt          0.0789
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      1.005
_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 0.0000 -0.02863(2) 0.2500 0.02196(10) Uani 1 2 d S T P B .
O1 O 0.10326(7) -0.05158(8) 0.19173(12) 0.0297(2) Uani 1 1 d . . . . .
O2 O 0.08105(7) 0.02766(7) -0.02033(12) 0.0265(2) Uani 1 1 d . . . . .
C1 C 0.11421(8) -0.03881(9) 0.07657(16) 0.0234(3) Uani 1 1 d D . . . .
C2 C 0.17377(13) -0.10531(14) 0.0475(3) 0.0262(4) Uani 0.877(3) 1 d . . P A 1
C3 C 0.21266(11) -0.06943(13) -0.0399(2) 0.0294(4) Uani 0.877(3) 1 d . . P A 1
H3A H 0.2084 -0.0035 -0.0663 0.035 Uiso 0.877(3) 1 calc R U P A 1
C4 C 0.25658(11) -0.13249(13) -0.0853(2) 0.0319(4) Uani 0.877(3) 1 d . . P A 1
C5 C 0.23206(12) -0.26670(15) 0.0473(2) 0.0286(4) Uani 0.877(3) 1 d . . P A 1
C6 C 0.18443(11) -0.20150(13) 0.0918(2) 0.0285(4) Uani 0.877(3) 1 d . . P A 1
H6A H 0.1602 -0.2247 0.1520 0.034 Uiso 0.877(3) 1 calc R U P A 1
N1 N 0.28517(15) -0.0910(2) -0.1909(3) 0.0500(6) Uani 0.877(3) 1 d . . P A 1
O3 O 0.32046(17) -0.01344(18) -0.1607(3) 0.0775(7) Uani 0.877(3) 1 d . . P A 1
O4 O 0.26498(19) -0.1350(2) -0.3110(3) 0.0736(7) Uani 0.877(3) 1 d . . P A 1
C2' C 0.1672(12) -0.1305(12) 0.068(2) 0.0262(4) Uani 0.123(3) 1 d D . P A 2
C3' C 0.1728(8) -0.2136(9) 0.1539(18) 0.0294(4) Uani 0.123(3) 1 d . . P A 2
H3B H 0.1501 -0.2141 0.2227 0.035 Uiso 0.123(3) 1 calc R U P A 2
C4' C 0.2122(9) -0.2943(9) 0.1347(16) 0.035(3) Uani 0.123(3) 1 d . . P A 2
C5' C 0.2501(10) -0.2038(11) -0.0413(18) 0.0286(4) Uani 0.123(3) 1 d . . P A 2
C6' C 0.2027(8) -0.1213(11) -0.0230(14) 0.0285(4) Uani 0.123(3) 1 d . . P A 2
H6B H 0.1978 -0.0631 -0.0754 0.034 Uiso 0.123(3) 1 calc R U P A 2
N1' N 0.2029(14) -0.3921(18) 0.204(3) 0.0500(6) Uani 0.123(3) 1 d D . P A 2
O3' O 0.1540(13) -0.4555(14) 0.125(2) 0.0775(7) Uani 0.123(3) 1 d D . P A 2
O4' O 0.2237(16) -0.3806(17) 0.340(2) 0.0736(7) Uani 0.123(3) 1 d D . P A 2
C7 C 0.0349(9) 0.1841(6) 0.1835(13) 0.0323(9) Uani 0.5 1 d D . P B -1
H7A H 0.0645 0.1541 0.1372 0.039 Uiso 0.5 1 calc R U P B -1
C8 C 0.0287(3) 0.2864(4) 0.1807(9) 0.0362(12) Uani 0.5 1 d D . P B -1
H8A H 0.0575 0.3233 0.1392 0.043 Uiso 0.5 1 calc R U P B -1
C9 C -0.0480(9) 0.1761(6) 0.3064(13) 0.0323(9) Uani 0.5 1 d D . P B -1
H9A H -0.0746 0.1384 0.3510 0.039 Uiso 0.5 1 calc R U P B -1
C10 C -0.0594(3) 0.2755(4) 0.3013(8) 0.0326(11) Uani 0.5 1 d D . P B -1
H10A H -0.0936 0.3037 0.3396 0.039 Uiso 0.5 1 calc R U P B -1
C11 C -0.01943(17) 0.33323(19) 0.2385(6) 0.0302(8) Uani 0.5 1 d . . P B -1
C12 C -0.0302(2) 0.4408(2) 0.2337(5) 0.0399(8) Uani 0.5 1 d . . P B -1
H12A H -0.0836 0.4652 0.2076 0.048 Uiso 0.5 1 calc R U P B -1
C13 C 0.0299(2) 0.5034(3) 0.2633(5) 0.0436(8) Uani 0.5 1 d . . P B -1
H13A H 0.0829 0.4787 0.2863 0.052 Uiso 0.5 1 calc R U P B -1
C14 C 0.0206(2) 0.6113(2) 0.2633(7) 0.0352(9) Uani 0.5 1 d . . P B -1
C15 C 0.0861(3) 0.6703(5) 0.3602(9) 0.0400(12) Uani 0.5 1 d D . P B -1
H15A H 0.1363 0.6428 0.4291 0.048 Uiso 0.5 1 calc R U P B -1
C16 C 0.0748(6) 0.7721(6) 0.3518(8) 0.0387(6) Uani 0.5 1 d D . P B -1
H16A H 0.1185 0.8120 0.4158 0.046 Uiso 0.5 1 calc R U P B -1
C17 C -0.0537(4) 0.6569(4) 0.1662(8) 0.0384(12) Uani 0.5 1 d D . P B -1
H17A H -0.0993 0.6193 0.1022 0.046 Uiso 0.5 1 calc R U P B -1
C18 C -0.0600(6) 0.7577(6) 0.1649(9) 0.0387(6) Uani 0.5 1 d D . P B -1
H18A H -0.1105 0.7860 0.0986 0.046 Uiso 0.5 1 calc R U P B -1
N2 N 0.0000 0.12869(11) 0.2500 0.0252(3) Uani 1 2 d DS T P . .
N3 N 0.0000 0.81536(12) 0.2500 0.0340(4) Uani 1 2 d DS T P . .


_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 2.0802(11) 6_556 ?
Co1 O2 2.0802(11) 5 ?
Co1 N3 2.1268(17) 1_545 ?
Co1 N2 2.1446(16) . ?
Co1 O1 2.1758(10) . ?
Co1 O1 2.1758(10) 2 ?
O1 C1 1.2466(18) . ?
O2 C1 1.2589(17) . ?
O2 Co1 2.0802(11) 5 ?
C1 C2 1.515(2) . ?
C1 C2' 1.588(15) . ?
C2 C6 1.369(2) . ?
C2 C3 1.410(2) . ?
C3 C4 1.363(2) . ?
C3 H3A 0.9300 . ?
C4 C5 1.415(3) 7_545 ?
C4 N1 1.460(3) . ?
C5 C4 1.415(3) 7_545 ?
C5 C5 1.418(4) 7_545 ?
C5 C6 1.425(3) . ?
C6 H6A 0.9300 . ?
N1 O3 1.198(4) . ?
N1 O4 1.231(4) . ?
C2' C6' 1.32(2) . ?
C2' C3' 1.39(2) . ?
C3' C4' 1.363(17) . ?
C3' H3B 0.9300 . ?
C4' C5' 1.358(19) 7_545 ?
C4' N1' 1.54(3) . ?
C5' C4' 1.358(19) 7_545 ?
C5' C6' 1.463(19) . ?
C5' C5' 1.50(3) 7_545 ?
C6' H6B 0.9300 . ?
N1' O3' 1.233(18) . ?
N1' O4' 1.228(18) . ?
C7 N2 1.321(11) . ?
C7 C8 1.398(9) . ?
C7 H7A 0.9300 . ?
C8 C11 1.378(6) . ?
C8 H8A 0.9300 . ?
C9 N2 1.370(11) . ?
C9 C10 1.367(10) . ?
C9 H9A 0.9300 . ?
C10 C11 1.377(6) . ?
C10 H10A 0.9300 . ?
C11 C12 1.476(4) . ?
C12 C13 1.297(5) . ?
C12 H12A 0.9300 . ?
C13 C14 1.480(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.392(6) . ?
C14 C17 1.390(7) . ?
C15 C16 1.398(10) . ?
C15 H15A 0.9300 . ?
C16 N3 1.396(11) . ?
C16 H16A 0.9300 . ?
C17 C18 1.379(8) . ?
C17 H17A 0.9300 . ?
C18 N3 1.292(12) . ?
C18 H18A 0.9300 . ?
N3 Co1 2.1268(17) 1_565 ?

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 O2 179.27(5) 6_556 5 ?
O2 Co1 N3 90.36(3) 6_556 1_545 ?
O2 Co1 N3 90.36(3) 5 1_545 ?
O2 Co1 N2 89.64(3) 6_556 . ?
O2 Co1 N2 89.64(3) 5 . ?
N3 Co1 N2 180.0 1_545 . ?
O2 Co1 O1 91.65(4) 6_556 . ?
O2 Co1 O1 88.46(4) 5 . ?
N3 Co1 O1 81.73(3) 1_545 . ?
N2 Co1 O1 98.27(3) . . ?
O2 Co1 O1 88.46(4) 6_556 2 ?
O2 Co1 O1 91.65(4) 5 2 ?
N3 Co1 O1 81.73(3) 1_545 2 ?
N2 Co1 O1 98.27(3) . 2 ?
O1 Co1 O1 163.46(6) . 2 ?
C1 O1 Co1 135.27(9) . . ?
C1 O2 Co1 134.31(9) . 5 ?
O1 C1 O2 125.67(12) . . ?
O1 C1 C2 119.51(13) . . ?
O2 C1 C2 114.80(13) . . ?
O1 C1 C2' 105.7(7) . . ?
O2 C1 C2' 128.1(7) . . ?
C6 C2 C3 119.42(17) . . ?
C6 C2 C1 121.53(16) . . ?
C3 C2 C1 118.76(15) . . ?
C4 C3 C2 119.29(17) . . ?
C4 C3 H3A 120.4 . . ?
C2 C3 H3A 120.4 . . ?
C3 C4 C5 124.09(17) . 7_545 ?
C3 C4 N1 114.87(17) . . ?
C5 C4 N1 120.77(17) 7_545 . ?
C4 C5 C5 115.7(2) 7_545 7_545 ?
C4 C5 C6 123.97(17) 7_545 . ?
C5 C5 C6 120.3(2) 7_545 . ?
C2 C6 C5 121.13(17) . . ?
C2 C6 H6A 119.4 . . ?
C5 C6 H6A 119.4 . . ?
O3 N1 O4 124.6(3) . . ?
O3 N1 C4 118.3(2) . . ?
O4 N1 C4 116.9(3) . . ?
C6' C2' C3' 124.5(14) . . ?
C6' C2' C1 115.8(12) . . ?
C3' C2' C1 119.7(13) . . ?
C2' C3' C4' 118.5(15) . . ?
C2' C3' H3B 120.7 . . ?
C4' C3' H3B 120.7 . . ?
C5' C4' C3' 123.3(13) 7_545 . ?
C5' C4' N1' 117.9(13) 7_545 . ?
C3' C4' N1' 118.2(13) . . ?
C4' C5' C6' 125.6(14) 7_545 . ?
C4' C5' C5' 118.2(17) 7_545 7_545 ?
C6' C5' C5' 116.0(16) . 7_545 ?
C2' C6' C5' 119.3(14) . . ?
C2' C6' H6B 120.4 . . ?
C5' C6' H6B 120.4 . . ?
O3' N1' O4' 125(2) . . ?
O3' N1' C4' 120.4(19) . . ?
O4' N1' C4' 109.5(19) . . ?
N2 C7 C8 122.0(6) . . ?
N2 C7 H7A 119.0 . . ?
C8 C7 H7A 119.0 . . ?
C11 C8 C7 120.8(6) . . ?
C11 C8 H8A 119.6 . . ?
C7 C8 H8A 119.6 . . ?
N2 C9 C10 124.1(6) . . ?
N2 C9 H9A 117.9 . . ?
C10 C9 H9A 117.9 . . ?
C11 C10 C9 119.1(6) . . ?
C11 C10 H10A 120.5 . . ?
C9 C10 H10A 120.5 . . ?
C10 C11 C8 117.4(2) . . ?
C10 C11 C12 119.8(4) . . ?
C8 C11 C12 122.8(4) . . ?
C13 C12 C11 124.4(3) . . ?
C13 C12 H12A 117.8 . . ?
C11 C12 H12A 117.8 . . ?
C12 C13 C14 125.0(3) . . ?
C12 C13 H13A 117.5 . . ?
C14 C13 H13A 117.5 . . ?
C15 C14 C17 117.9(3) . . ?
C15 C14 C13 121.0(4) . . ?
C17 C14 C13 121.1(4) . . ?
C14 C15 C16 118.6(6) . . ?
C14 C15 H15A 120.7 . . ?
C16 C15 H15A 120.7 . . ?
N3 C16 C15 121.9(5) . . ?
N3 C16 H16A 119.1 . . ?
C15 C16 H16A 119.1 . . ?
C18 C17 C14 120.0(6) . . ?
C18 C17 H17A 120.0 . . ?
C14 C17 H17A 120.0 . . ?
N3 C18 C17 124.1(6) . . ?
N3 C18 H18A 118.0 . . ?
C17 C18 H18A 118.0 . . ?
C7 N2 C9 116.5(3) . . ?
C7 N2 Co1 124.9(3) . . ?
C9 N2 Co1 118.2(3) . . ?
C18 N3 C16 117.5(3) . . ?
C18 N3 Co1 127.4(2) . 1_565 ?
C16 N3 Co1 115.0(2) . 1_565 ?

_refine_diff_density_max         0.336
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.054

_shelxl_version_number           2014-3

