# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

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

data_NTU-40
_database_code_depnum_ccdc_archive 'CCDC 1827234'
_audit_update_record             
;
2018-03-03 deposited with the CCDC.
2018-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H8 Co N2 O4'
_chemical_formula_weight         303.13

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

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

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

_cell_length_a                   12.9362(19)
_cell_length_b                   14.560(2)
_cell_length_c                   20.181(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3801.1(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3191
_cell_measurement_theta_min      2.333
_cell_measurement_theta_max      24.067

_exptl_crystal_description       block
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.059
_exptl_crystal_F_000             1224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.910
_shelx_estimated_absorpt_T_min   0.876
_shelx_estimated_absorpt_T_max   0.915
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker smart CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25701
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_av_R_equivalents  0.0740
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.018
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3527
_reflns_number_gt                2406
_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-2013 (Sheldrick, 2013)'
_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)+(0.1025P)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         3527
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1671
_refine_ls_wR_factor_gt          0.1546
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
C1 C 0.1173(3) 1.0163(3) 0.30324(19) 0.0276(9) Uani 1 1 d . . . . .
C2 C 0.1829(3) 0.9470(3) 0.33899(19) 0.0274(9) Uani 1 1 d . . . . .
C3 C 0.1756(3) 0.9394(3) 0.4068(2) 0.0328(10) Uani 1 1 d . . . . .
H3 H 0.1307 0.9776 0.4299 0.039 Uiso 1 1 calc R U . . .
C4 C 0.2347(3) 0.8751(3) 0.44118(19) 0.0295(10) Uani 1 1 d . . . . .
C5 C 0.3030(3) 0.8200(3) 0.4075(2) 0.0326(10) Uani 1 1 d . . . . .
H5 H 0.3449 0.7792 0.4306 0.039 Uiso 1 1 calc R U . . .
C6 C 0.3096(3) 0.8253(3) 0.33928(19) 0.0300(9) Uani 1 1 d . . . . .
C7 C 0.2494(3) 0.8886(2) 0.30430(19) 0.0294(9) Uani 1 1 d . . . . .
H7 H 0.2535 0.8918 0.2584 0.035 Uiso 1 1 calc R U . . .
C8 C 0.3801(3) 0.7613(3) 0.30289(19) 0.0252(9) Uani 1 1 d . . . . .
C9 C 0.0312(4) 0.8586(4) 0.5212(2) 0.0485(13) Uani 1 1 d . . . . .
H9A H 0.0003 0.8010 0.5331 0.073 Uiso 1 1 calc R U . . .
H9B H 0.0338 0.8639 0.4738 0.073 Uiso 1 1 calc R U . . .
H9C H -0.0092 0.9080 0.5390 0.073 Uiso 1 1 calc R U . . .
C10 C 0.1371(3) 0.8632(3) 0.54824(19) 0.0274(9) Uani 1 1 d . . . . .
C11 C 0.2661(3) 0.8640(3) 0.6156(2) 0.0399(11) Uani 1 1 d . . . . .
H11 H 0.3036 0.8637 0.6549 0.048 Uiso 1 1 calc R U . . .
C12 C 0.3084(3) 0.8684(3) 0.5547(2) 0.0396(11) Uani 1 1 d . . . . .
H12 H 0.3783 0.8707 0.5441 0.048 Uiso 1 1 calc R U . . .
Co1 Co -0.06718(4) 1.13907(3) 0.30646(2) 0.0194(2) Uani 1 1 d . . . . .
N1 N 0.2262(2) 0.8690(2) 0.51149(15) 0.0282(8) Uani 1 1 d . . . . .
N2 N 0.1612(2) 0.8599(2) 0.61201(15) 0.0260(7) Uani 1 1 d . . . . .
O1 O 0.0364(2) 1.0415(2) 0.33266(15) 0.0423(8) Uani 1 1 d . . . . .
O2 O 0.1458(2) 1.0422(2) 0.24709(14) 0.0387(8) Uani 1 1 d . . . . .
O3 O 0.3583(2) 0.7406(2) 0.24469(14) 0.0376(7) Uani 1 1 d . . . . .
O4 O 0.4567(2) 0.7316(2) 0.33513(14) 0.0392(8) 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
C1 O2 1.250(5) . ?
C1 O1 1.258(5) . ?
C1 C2 1.503(5) . ?
C2 C3 1.376(5) . ?
C2 C7 1.397(5) . ?
C3 C4 1.395(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(5) . ?
C4 N1 1.426(5) . ?
C5 C6 1.381(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.398(5) . ?
C6 C8 1.496(5) . ?
C7 H7 0.9300 . ?
C8 O3 1.245(4) . ?
C8 O4 1.263(5) . ?
C9 C10 1.477(6) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 N2 1.325(5) . ?
C10 N1 1.373(5) . ?
C11 C12 1.348(6) . ?
C11 N2 1.359(5) . ?
C11 H11 0.9300 . ?
C12 N1 1.374(5) . ?
C12 H12 0.9300 . ?
Co1 O1 2.023(3) . ?
Co1 O3 2.044(3) 6_566 ?
Co1 N2 2.046(3) 5_576 ?
Co1 O2 2.047(3) 3 ?
Co1 O4 2.047(3) 8_665 ?
Co1 Co1 2.8661(10) 3 ?
N2 Co1 2.046(3) 5_576 ?
O2 Co1 2.046(3) 3 ?
O3 Co1 2.044(3) 6_656 ?
O4 Co1 2.047(3) 8_655 ?

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 C1 O1 125.8(4) . . ?
O2 C1 C2 118.1(3) . . ?
O1 C1 C2 116.1(3) . . ?
C3 C2 C7 119.5(3) . . ?
C3 C2 C1 119.5(3) . . ?
C7 C2 C1 121.0(3) . . ?
C2 C3 C4 120.7(4) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 119.9(4) . . ?
C5 C4 N1 120.4(3) . . ?
C3 C4 N1 119.7(3) . . ?
C4 C5 C6 120.0(4) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C7 120.4(4) . . ?
C5 C6 C8 119.5(4) . . ?
C7 C6 C8 120.1(3) . . ?
C2 C7 C6 119.4(3) . . ?
C2 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
O3 C8 O4 125.5(4) . . ?
O3 C8 C6 118.5(3) . . ?
O4 C8 C6 116.1(3) . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 N1 109.2(3) . . ?
N2 C10 C9 125.2(4) . . ?
N1 C10 C9 125.6(3) . . ?
C12 C11 N2 111.0(4) . . ?
C12 C11 H11 124.5 . . ?
N2 C11 H11 124.5 . . ?
C11 C12 N1 105.4(4) . . ?
C11 C12 H12 127.3 . . ?
N1 C12 H12 127.3 . . ?
O1 Co1 O3 162.16(12) . 6_566 ?
O1 Co1 N2 100.87(13) . 5_576 ?
O3 Co1 N2 96.92(12) 6_566 5_576 ?
O1 Co1 O2 89.03(13) . 3 ?
O3 Co1 O2 89.83(12) 6_566 3 ?
N2 Co1 O2 97.72(13) 5_576 3 ?
O1 Co1 O4 85.75(14) . 8_665 ?
O3 Co1 O4 89.79(12) 6_566 8_665 ?
N2 Co1 O4 100.54(13) 5_576 8_665 ?
O2 Co1 O4 161.65(12) 3 8_665 ?
O1 Co1 Co1 78.83(9) . 3 ?
O3 Co1 Co1 83.37(8) 6_566 3 ?
N2 Co1 Co1 179.05(10) 5_576 3 ?
O2 Co1 Co1 83.18(8) 3 3 ?
O4 Co1 Co1 78.55(9) 8_665 3 ?
C10 N1 C12 107.8(3) . . ?
C10 N1 C4 127.3(3) . . ?
C12 N1 C4 124.9(3) . . ?
C10 N2 C11 106.6(3) . . ?
C10 N2 Co1 129.9(3) . 5_576 ?
C11 N2 Co1 123.3(3) . 5_576 ?
C1 O1 Co1 129.2(3) . . ?
C1 O2 Co1 122.7(3) . 3 ?
C8 O3 Co1 123.1(3) . 6_656 ?
C8 O4 Co1 128.9(3) . 8_655 ?

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
O2 C1 C2 C3 158.4(4) . . . . ?
O1 C1 C2 C3 -23.0(6) . . . . ?
O2 C1 C2 C7 -23.3(6) . . . . ?
O1 C1 C2 C7 155.3(4) . . . . ?
C7 C2 C3 C4 0.9(6) . . . . ?
C1 C2 C3 C4 179.3(4) . . . . ?
C2 C3 C4 C5 1.6(6) . . . . ?
C2 C3 C4 N1 179.5(4) . . . . ?
C3 C4 C5 C6 -3.1(6) . . . . ?
N1 C4 C5 C6 178.9(4) . . . . ?
C4 C5 C6 C7 2.1(7) . . . . ?
C4 C5 C6 C8 -176.7(4) . . . . ?
C3 C2 C7 C6 -1.9(6) . . . . ?
C1 C2 C7 C6 179.8(4) . . . . ?
C5 C6 C7 C2 0.4(6) . . . . ?
C8 C6 C7 C2 179.2(4) . . . . ?
C5 C6 C8 O3 152.4(4) . . . . ?
C7 C6 C8 O3 -26.4(6) . . . . ?
C5 C6 C8 O4 -26.3(6) . . . . ?
C7 C6 C8 O4 154.9(4) . . . . ?
N2 C11 C12 N1 1.2(5) . . . . ?
N2 C10 N1 C12 0.5(5) . . . . ?
C9 C10 N1 C12 -177.8(4) . . . . ?
N2 C10 N1 C4 -179.2(3) . . . . ?
C9 C10 N1 C4 2.4(7) . . . . ?
C11 C12 N1 C10 -1.0(5) . . . . ?
C11 C12 N1 C4 178.7(4) . . . . ?
C5 C4 N1 C10 -132.6(4) . . . . ?
C3 C4 N1 C10 49.4(6) . . . . ?
C5 C4 N1 C12 47.7(6) . . . . ?
C3 C4 N1 C12 -130.3(4) . . . . ?
N1 C10 N2 C11 0.2(5) . . . . ?
C9 C10 N2 C11 178.6(4) . . . . ?
N1 C10 N2 Co1 174.7(2) . . . 5_576 ?
C9 C10 N2 Co1 -6.9(6) . . . 5_576 ?
C12 C11 N2 C10 -0.9(5) . . . . ?
C12 C11 N2 Co1 -175.8(3) . . . 5_576 ?
O2 C1 O1 Co1 -6.7(6) . . . . ?
C2 C1 O1 Co1 174.8(3) . . . . ?
O1 C1 O2 Co1 3.6(6) . . . 3 ?
C2 C1 O2 Co1 -178.0(3) . . . 3 ?
O4 C8 O3 Co1 8.7(6) . . . 6_656 ?
C6 C8 O3 Co1 -169.9(3) . . . 6_656 ?
O3 C8 O4 Co1 -1.9(6) . . . 8_655 ?
C6 C8 O4 Co1 176.7(3) . . . 8_655 ?


loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.018 0.278 0.754 1897 439 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?


_refine_diff_density_max         0.486
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.088

_shelxl_version_number           2013-2



####################################################################### 
# 
# 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_a_sqd
_database_code_depnum_ccdc_archive 'CCDC 1827235'
_audit_update_record             
;
2018-03-03 deposited with the CCDC.
2018-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H8 Co N2 O4'
_chemical_formula_weight         303.13

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/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                   10.9005(10)
_cell_length_b                   11.3760(12)
_cell_length_c                   14.8416(15)
_cell_angle_alpha                90
_cell_angle_beta                 109.352(3)
_cell_angle_gamma                90
_cell_volume                     1736.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9993
_cell_measurement_theta_min      2.306
_cell_measurement_theta_max      26.354

_exptl_crystal_description       block
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_F_000             612
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.996
_shelx_estimated_absorpt_T_min   0.890
_shelx_estimated_absorpt_T_max   0.916
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71076
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker smart ccd'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36353
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_av_R_equivalents  0.0984
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.307
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_full        25.243
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             3074
_reflns_number_gt                2519
_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-2013 (Sheldrick, 2013)'
_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)+(0.1700P)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         3074
_refine_ls_number_parameters     170
_refine_ls_number_restraints     145
_refine_ls_R_factor_all          0.1046
_refine_ls_R_factor_gt           0.0823
_refine_ls_wR_factor_ref         0.2306
_refine_ls_wR_factor_gt          0.2124
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.039
_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
C1 C 0.1280(5) 0.1110(5) 0.1529(4) 0.0196(13) Uani 1 1 d . U . . .
C2 C 0.2044(5) 0.1807(5) 0.2395(4) 0.0211(12) Uani 1 1 d . U . . .
C3 C 0.1390(5) 0.2511(5) 0.2837(4) 0.0173(12) Uani 1 1 d . U . . .
H3 H 0.0486 0.2543 0.2604 0.021 Uiso 1 1 calc R U . . .
C4 C 0.2069(5) 0.3167(5) 0.3623(4) 0.0203(12) Uani 1 1 d . U . . .
C5 C 0.3422(5) 0.3154(5) 0.3943(4) 0.0226(13) Uani 1 1 d . U . . .
H5 H 0.3891 0.3621 0.4456 0.027 Uiso 1 1 calc R U . . .
C6 C 0.4054(5) 0.2443(5) 0.3491(4) 0.0179(12) Uani 1 1 d . U . . .
C7 C 0.3389(5) 0.1765(5) 0.2722(4) 0.0236(13) Uani 1 1 d . U . . .
H7 H 0.3832 0.1286 0.2426 0.028 Uiso 1 1 calc R U . . .
C8 C 0.1337(5) 0.3903(5) 0.4128(4) 0.0193(13) Uani 1 1 d . U . . .
C9 C 0.6264(5) 0.3318(5) 0.4110(4) 0.0215(13) Uani 1 1 d . U . . .
H9 H 0.6002 0.4094 0.4119 0.026 Uiso 1 1 calc R U . . .
C10 C 0.7470(6) 0.1771(5) 0.4237(5) 0.0321(16) Uani 1 1 d . U . . .
C11 C 0.6212(6) 0.1415(6) 0.3902(6) 0.0369(17) Uani 1 1 d . U . . .
H11 H 0.5915 0.0651 0.3745 0.044 Uiso 1 1 calc R U . . .
Co1 Co -0.09801(6) 0.08964(6) -0.02270(5) 0.0128(3) Uani 1 1 d . . . . .
N1 N 0.5465(4) 0.2401(4) 0.3837(4) 0.0187(11) Uani 1 1 d . . . . .
N2 N 0.7497(4) 0.2952(4) 0.4370(3) 0.0181(11) Uani 1 1 d . . . . .
O1 O 0.0210(4) 0.1505(4) 0.1038(3) 0.0314(11) Uani 1 1 d . . . . .
O2 O 0.1805(4) 0.0194(4) 0.1364(3) 0.0324(11) Uani 1 1 d . . . . .
O3 O 0.0259(4) 0.3522(4) 0.4112(3) 0.0288(10) Uani 1 1 d . . . . .
O4 O 0.1861(3) 0.4824(3) 0.4525(3) 0.0290(11) Uani 1 1 d . . . . .
C12 C 0.8812(3) 0.1000(3) 0.4516(3) 0.0369(17) Uani 1 1 d R U . . .
H12A H 0.8977 0.0648 0.5132 0.055 Uiso 1 1 calc R U . . .
H12B H 0.9524 0.1506 0.4531 0.055 Uiso 1 1 calc R U . . .
H12C H 0.8723 0.0396 0.4047 0.055 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
C1 O1 1.237(7) . ?
C1 O2 1.252(7) . ?
C1 C2 1.505(8) . ?
C2 C3 1.374(8) . ?
C2 C7 1.384(8) . ?
C3 C4 1.377(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(8) . ?
C4 C8 1.515(8) . ?
C5 C6 1.374(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.369(8) . ?
C6 N1 1.452(7) . ?
C7 H7 0.9300 . ?
C8 O4 1.245(7) . ?
C8 O3 1.246(7) . ?
C9 N1 1.332(7) . ?
C9 N2 1.336(7) . ?
C9 H9 0.9300 . ?
C10 N2 1.357(8) . ?
C10 C11 1.356(9) . ?
C10 C12 1.637(7) . ?
C11 N1 1.371(8) . ?
C11 H11 0.9300 . ?
Co1 O3 2.026(4) 4_565 ?
Co1 O1 2.018(4) . ?
Co1 O4 2.039(4) 2_545 ?
Co1 O2 2.046(4) 3 ?
Co1 N2 2.042(4) 4_465 ?
Co1 Co1 2.8679(13) 3 ?
N2 Co1 2.042(4) 4_666 ?
O2 Co1 2.046(4) 3 ?
O3 Co1 2.026(4) 4_566 ?
O4 Co1 2.039(4) 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
O1 C1 O2 126.2(5) . . ?
O1 C1 C2 117.3(5) . . ?
O2 C1 C2 116.5(5) . . ?
C3 C2 C7 120.6(5) . . ?
C3 C2 C1 119.1(5) . . ?
C7 C2 C1 120.2(5) . . ?
C2 C3 C4 120.1(5) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 119.7(5) . . ?
C5 C4 C8 120.6(5) . . ?
C3 C4 C8 119.7(5) . . ?
C6 C5 C4 119.1(5) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C7 C6 C5 121.7(5) . . ?
C7 C6 N1 118.9(5) . . ?
C5 C6 N1 119.4(5) . . ?
C6 C7 C2 118.7(5) . . ?
C6 C7 H7 120.7 . . ?
C2 C7 H7 120.7 . . ?
O4 C8 O3 125.7(5) . . ?
O4 C8 C4 117.8(5) . . ?
O3 C8 C4 116.6(5) . . ?
N1 C9 N2 109.7(5) . . ?
N1 C9 H9 125.1 . . ?
N2 C9 H9 125.1 . . ?
N2 C10 C11 108.6(5) . . ?
N2 C10 C12 121.3(5) . . ?
C11 C10 C12 130.0(5) . . ?
N1 C11 C10 106.6(5) . . ?
N1 C11 H11 126.7 . . ?
C10 C11 H11 126.7 . . ?
O3 Co1 O1 90.70(18) 4_565 . ?
O3 Co1 O4 160.96(16) 4_565 2_545 ?
O1 Co1 O4 89.82(18) . 2_545 ?
O3 Co1 O2 88.83(18) 4_565 3 ?
O1 Co1 O2 161.15(18) . 3 ?
O4 Co1 O2 84.61(17) 2_545 3 ?
O3 Co1 N2 104.85(18) 4_565 4_465 ?
O1 Co1 N2 105.19(19) . 4_465 ?
O4 Co1 N2 93.36(16) 2_545 4_465 ?
O2 Co1 N2 93.13(18) 3 4_465 ?
O3 Co1 Co1 77.38(12) 4_565 3 ?
O1 Co1 Co1 80.00(13) . 3 ?
O4 Co1 Co1 83.97(10) 2_545 3 ?
O2 Co1 Co1 81.51(13) 3 3 ?
N2 Co1 Co1 174.20(14) 4_465 3 ?
C11 N1 C9 107.8(5) . . ?
C11 N1 C6 125.9(5) . . ?
C9 N1 C6 126.2(4) . . ?
C10 N2 C9 107.2(5) . . ?
C10 N2 Co1 130.8(4) . 4_666 ?
C9 N2 Co1 121.8(4) . 4_666 ?
C1 O1 Co1 127.8(4) . . ?
C1 O2 Co1 124.2(4) . 3 ?
C8 O3 Co1 130.8(4) . 4_566 ?
C8 O4 Co1 121.8(4) . 2 ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 27.1(8) . . . . ?
O2 C1 C2 C3 -154.2(6) . . . . ?
O1 C1 C2 C7 -150.9(6) . . . . ?
O2 C1 C2 C7 27.8(8) . . . . ?
C7 C2 C3 C4 -1.2(9) . . . . ?
C1 C2 C3 C4 -179.2(5) . . . . ?
C2 C3 C4 C5 2.8(9) . . . . ?
C2 C3 C4 C8 -177.6(5) . . . . ?
C3 C4 C5 C6 -2.8(9) . . . . ?
C8 C4 C5 C6 177.6(5) . . . . ?
C4 C5 C6 C7 1.3(9) . . . . ?
C4 C5 C6 N1 -178.4(5) . . . . ?
C5 C6 C7 C2 0.2(9) . . . . ?
N1 C6 C7 C2 180.0(5) . . . . ?
C3 C2 C7 C6 -0.3(9) . . . . ?
C1 C2 C7 C6 177.6(6) . . . . ?
C5 C4 C8 O4 30.2(8) . . . . ?
C3 C4 C8 O4 -149.3(6) . . . . ?
C5 C4 C8 O3 -149.3(6) . . . . ?
C3 C4 C8 O3 31.1(8) . . . . ?
N2 C10 C11 N1 -0.4(8) . . . . ?
C12 C10 C11 N1 176.6(6) . . . . ?
C10 C11 N1 C9 1.2(8) . . . . ?
C10 C11 N1 C6 178.6(6) . . . . ?
N2 C9 N1 C11 -1.5(7) . . . . ?
N2 C9 N1 C6 -178.9(5) . . . . ?
C7 C6 N1 C11 -39.4(9) . . . . ?
C5 C6 N1 C11 140.3(7) . . . . ?
C7 C6 N1 C9 137.5(6) . . . . ?
C5 C6 N1 C9 -42.7(8) . . . . ?
C11 C10 N2 C9 -0.4(8) . . . . ?
C12 C10 N2 C9 -177.8(5) . . . . ?
C11 C10 N2 Co1 -175.6(5) . . . 4_666 ?
C12 C10 N2 Co1 7.0(9) . . . 4_666 ?
N1 C9 N2 C10 1.2(7) . . . . ?
N1 C9 N2 Co1 176.9(4) . . . 4_666 ?
O2 C1 O1 Co1 -5.1(9) . . . . ?
C2 C1 O1 Co1 173.4(4) . . . . ?
O1 C1 O2 Co1 -0.8(9) . . . 3 ?
C2 C1 O2 Co1 -179.4(4) . . . 3 ?
O4 C8 O3 Co1 -5.8(9) . . . 4_566 ?
C4 C8 O3 Co1 173.7(4) . . . 4_566 ?
O3 C8 O4 Co1 -0.6(8) . . . 2 ?
C4 C8 O4 Co1 179.9(4) . . . 2 ?

_refine_diff_density_max         2.467
_refine_diff_density_min         -0.845
_refine_diff_density_rms         0.144

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.034 0.147 0.347 828 108 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?


_shelxl_version_number           2013-2



