# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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 2014292'
_audit_update_record             
;
2020-07-05 deposited with the CCDC.	2020-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H10 Co N4 O4'
_chemical_formula_weight         381.21

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   7.679(4)
_cell_length_b                   24.128(11)
_cell_length_c                   9.496(4)
_cell_angle_alpha                90
_cell_angle_beta                 113.85
_cell_angle_gamma                90
_cell_volume                     1609.2(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3076
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      27.89

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_F_000             772
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.096
_shelx_estimated_absorpt_T_min   0.827
_shelx_estimated_absorpt_T_max   0.947
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'bruker D8 VENTURE PHOTONII'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6340
_diffrn_reflns_av_unetI/netI     0.1303
_diffrn_reflns_av_R_equivalents  0.0864
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.492
_diffrn_reflns_theta_max         27.112
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.772
_diffrn_measured_fraction_theta_full 0.735
_diffrn_reflns_Laue_measured_fraction_max 0.772
_diffrn_reflns_Laue_measured_fraction_full 0.735
_diffrn_reflns_point_group_measured_fraction_max 0.772
_diffrn_reflns_point_group_measured_fraction_full 0.735
_reflns_number_total             2742
_reflns_number_gt                1729
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0869P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2742
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1155
_refine_ls_R_factor_gt           0.0710
_refine_ls_wR_factor_ref         0.1783
_refine_ls_wR_factor_gt          0.1618
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_restrained_S_all      0.964
_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 0.12926(11) 0.60882(3) 0.31747(9) 0.0211(2) Uani 1 1 d . . . . .
O1 O 0.3774(5) 0.59584(15) 0.4905(4) 0.0252(9) Uani 1 1 d . . . . .
N2 N 0.8177(7) 0.46971(18) 1.0790(6) 0.0245(11) Uani 1 1 d . . . . .
H1N2 H 0.7817 0.4322 1.0463 0.029 Uiso 1 1 d R U . . .
C1 C 0.3722(8) 0.5562(2) 0.5800(6) 0.0251(13) Uani 1 1 d . . . . .
O2 O 0.1668(6) 0.67548(16) 0.2155(5) 0.0307(10) Uani 1 1 d . . . . .
N1 N 0.9689(7) 0.54827(17) 1.1786(5) 0.0206(10) Uani 1 1 d . . . . .
H1N4 H 0.1112 0.8849 -0.0148 0.025 Uiso 1 1 d R U . . .
C2 C 0.5345(8) 0.5563(2) 0.7384(7) 0.0233(12) Uani 1 1 d . . . . .
O3 O 0.2453(6) 0.52166(16) 0.5436(5) 0.0359(11) Uani 1 1 d . . . . .
N4 N 0.2031(7) 0.86656(19) -0.0270(6) 0.0248(11) Uani 1 1 d . . . . .
C3 C 0.6322(8) 0.6061(2) 0.8006(7) 0.0248(12) Uani 1 1 d . . . . .
H3 H 0.5963 0.6390 0.7407 0.030 Uiso 1 1 calc R U . . .
O4 O 0.3219(7) 0.62078(17) 0.1185(6) 0.0383(12) Uani 1 1 d . . . . .
N3 N 0.4450(7) 0.86268(19) -0.0993(6) 0.0258(11) Uani 1 1 d . . . . .
C4 C 0.7787(8) 0.6086(2) 0.9465(6) 0.0257(13) Uani 1 1 d . . . . .
H4 H 0.8424 0.6424 0.9876 0.031 Uiso 1 1 calc R U . . .
C5 C 0.8285(8) 0.5592(2) 1.0300(7) 0.0215(12) Uani 1 1 d . . . . .
C6 C 0.7313(8) 0.5099(2) 0.9683(7) 0.0220(12) Uani 1 1 d . . . . .
C7 C 0.5840(8) 0.5071(2) 0.8218(7) 0.0213(12) Uani 1 1 d . . . . .
H7 H 0.5206 0.4732 0.7809 0.026 Uiso 1 1 calc R U . . .
C8 C 0.9540(8) 0.4946(2) 1.1984(7) 0.0249(12) Uani 1 1 d . . . . .
H8 H 1.0330 0.4755 1.2892 0.030 Uiso 1 1 calc R U . . .
C9 C 0.2667(9) 0.6673(2) 0.1384(7) 0.0297(14) Uani 1 1 d . . . . .
C10 C 0.3179(9) 0.7175(2) 0.0710(7) 0.0297(14) Uani 1 1 d . . . . .
C11 C 0.2164(9) 0.7668(2) 0.0615(7) 0.0283(13) Uani 1 1 d . . . . .
H11 H 0.1161 0.7690 0.0956 0.034 Uiso 1 1 calc R U . . .
C12 C 0.2714(8) 0.8119(2) -0.0003(7) 0.0264(13) Uani 1 1 d . . . . .
C13 C 0.4213(9) 0.8103(2) -0.0453(7) 0.0262(13) Uani 1 1 d . . . . .
C14 C 0.5258(9) 0.7606(2) -0.0335(8) 0.0359(15) Uani 1 1 d . . . . .
H14 H 0.6289 0.7587 -0.0644 0.043 Uiso 1 1 calc R U . . .
C15 C 0.4684(10) 0.7155(2) 0.0255(8) 0.0361(16) Uani 1 1 d . . . . .
H15 H 0.5346 0.6814 0.0354 0.043 Uiso 1 1 calc R U . . .
C16 C 0.3113(9) 0.8938(2) -0.0843(7) 0.0247(12) Uani 1 1 d . . . . .
H16 H 0.2940 0.9319 -0.1117 0.030 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O2 1.958(4) . ?
Co1 O1 1.974(4) . ?
Co1 N3 2.001(5) 4_576 ?
Co1 N1 2.019(4) 1_454 ?
O1 C1 1.290(7) . ?
N2 C8 1.335(7) . ?
N2 C6 1.387(7) . ?
N2 H1N2 0.9600 . ?
C1 O3 1.221(7) . ?
C1 C2 1.517(8) . ?
O2 C9 1.272(8) . ?
N1 C8 1.320(7) . ?
N1 C5 1.411(7) . ?
N1 Co1 2.019(4) 1_656 ?
C2 C7 1.392(7) . ?
C2 C3 1.413(7) . ?
N4 C16 1.334(8) . ?
N4 C12 1.405(7) . ?
N4 H1N4 0.8793 . ?
C3 C4 1.388(7) . ?
C3 H3 0.9500 . ?
O4 C9 1.241(7) . ?
N3 C16 1.325(8) . ?
N3 C13 1.404(7) . ?
N3 Co1 2.001(5) 4_675 ?
C4 C5 1.397(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.400(7) . ?
C6 C7 1.396(8) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.495(8) . ?
C10 C15 1.389(9) . ?
C10 C11 1.405(8) . ?
C11 C12 1.380(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.380(9) . ?
C13 C14 1.421(8) . ?
C14 C15 1.377(8) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Co1 O1 104.87(17) . . ?
O2 Co1 N3 100.48(19) . 4_576 ?
O1 Co1 N3 108.93(19) . 4_576 ?
O2 Co1 N1 116.36(19) . 1_454 ?
O1 Co1 N1 123.88(17) . 1_454 ?
N3 Co1 N1 99.5(2) 4_576 1_454 ?
C1 O1 Co1 112.9(4) . . ?
C8 N2 C6 107.4(5) . . ?
C8 N2 H1N2 136.3 . . ?
C6 N2 H1N2 115.3 . . ?
O3 C1 O1 123.6(5) . . ?
O3 C1 C2 121.5(5) . . ?
O1 C1 C2 114.9(5) . . ?
C9 O2 Co1 113.6(4) . . ?
C8 N1 C5 104.5(4) . . ?
C8 N1 Co1 133.0(4) . 1_656 ?
C5 N1 Co1 122.4(3) . 1_656 ?
C7 C2 C3 120.7(5) . . ?
C7 C2 C1 119.3(5) . . ?
C3 C2 C1 120.0(5) . . ?
C16 N4 C12 106.7(5) . . ?
C16 N4 H1N4 118.2 . . ?
C12 N4 H1N4 135.1 . . ?
C4 C3 C2 122.2(5) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C16 N3 C13 104.4(5) . . ?
C16 N3 Co1 123.4(4) . 4_675 ?
C13 N3 Co1 132.1(4) . 4_675 ?
C3 C4 C5 117.1(5) . . ?
C3 C4 H4 121.5 . . ?
C5 C4 H4 121.5 . . ?
C4 C5 C6 120.6(5) . . ?
C4 C5 N1 130.5(5) . . ?
C6 C5 N1 108.8(4) . . ?
N2 C6 C7 131.9(5) . . ?
N2 C6 C5 105.4(5) . . ?
C7 C6 C5 122.7(5) . . ?
C2 C7 C6 116.7(5) . . ?
C2 C7 H7 121.6 . . ?
C6 C7 H7 121.6 . . ?
N1 C8 N2 113.8(5) . . ?
N1 C8 H8 123.1 . . ?
N2 C8 H8 123.1 . . ?
O4 C9 O2 123.5(6) . . ?
O4 C9 C10 120.1(6) . . ?
O2 C9 C10 116.4(6) . . ?
C15 C10 C11 121.3(6) . . ?
C15 C10 C9 120.0(6) . . ?
C11 C10 C9 118.6(6) . . ?
C12 C11 C10 115.9(6) . . ?
C12 C11 H11 122.0 . . ?
C10 C11 H11 122.0 . . ?
C11 C12 C13 123.1(6) . . ?
C11 C12 N4 131.4(6) . . ?
C13 C12 N4 105.5(5) . . ?
C12 C13 N3 109.6(5) . . ?
C12 C13 C14 121.0(5) . . ?
N3 C13 C14 129.4(6) . . ?
C15 C14 C13 115.8(6) . . ?
C15 C14 H14 122.1 . . ?
C13 C14 H14 122.1 . . ?
C14 C15 C10 122.8(6) . . ?
C14 C15 H15 118.6 . . ?
C10 C15 H15 118.6 . . ?
N3 C16 N4 113.7(5) . . ?
N3 C16 H16 123.1 . . ?
N4 C16 H16 123.1 . . ?

_refine_diff_density_max         1.229
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.105

####################################################################### 
# 
# 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 2014293'
_audit_update_record             
;
2020-07-05 deposited with the CCDC.	2020-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H10 Co N4 O4'
_chemical_formula_weight         381.21

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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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'

_cell_length_a                   14.8116(8)
_cell_length_b                   8.7686(4)
_cell_length_c                   14.8164(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1924.31(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7769
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      36.14

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_F_000             772
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.916
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'bruker D8 VENTURE PHOTONII'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32689
_diffrn_reflns_av_unetI/netI     0.0783
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.323
_diffrn_reflns_theta_max         36.591
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             9809
_reflns_number_gt                7270
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.942
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 4-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Twinning involves inversion, so Flack parameter cannot be determined
;
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         9809
_refine_ls_number_parameters     229
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1428
_refine_ls_wR_factor_gt          0.1149
_refine_ls_goodness_of_fit_ref   0.845
_refine_ls_restrained_S_all      0.845
_refine_ls_shift/su_max          0.010
_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 0.49016(3) 0.87516(17) 0.33801(3) 0.01716(10) Uani 1 1 d . . . . .
N1 N 0.5001(3) 0.1836(6) 0.7046(4) 0.0190(10) Uani 1 1 d . . . . .
C1 C 0.6309(3) 1.0515(5) 0.3455(5) 0.0236(9) Uani 1 1 d . . . . .
O1 O 0.54579(19) 1.0801(3) 0.3543(2) 0.0251(8) Uani 1 1 d . . . . .
O2 O 0.5064(2) 0.6720(5) 0.3965(2) 0.0250(7) Uani 1 1 d . . . . .
N2 N 0.7079(2) 1.6061(3) 0.3506(5) 0.0353(13) Uani 1 1 d . . . . .
H2 H 0.657092 1.653467 0.352961 0.042 Uiso 1 1 calc R U . . .
C2 C 0.6946(2) 1.1839(4) 0.3454(4) 0.0203(9) Uani 1 1 d . . . . .
O4 O 0.4896(4) 0.8315(7) 0.5068(5) 0.0369(14) Uani 1 1 d . . . . .
C4 C 0.7202(2) 1.4496(4) 0.3482(4) 0.0218(9) Uani 1 1 d . . . . .
N4 N 0.4935(3) 0.1462(5) 0.5570(3) 0.0300(11) Uani 1 1 d . . . . .
H4 H 0.491120 0.098871 0.506184 0.036 Uiso 1 1 calc R U . . .
C3 C 0.6592(3) 1.3304(4) 0.3471(4) 0.0219(9) Uani 1 1 d . . . . .
H3 H 0.597271 1.347573 0.347547 0.026 Uiso 1 1 calc R U . . .
O3 O 0.6586(4) 0.9181(5) 0.3387(5) 0.0408(14) Uani 1 1 d . . . . .
N3 N 0.8559(5) 1.5703(6) 0.3448(4) 0.0239(11) Uani 1 1 d . . . . .
C8 C 0.7908(3) 1.6700(4) 0.3485(6) 0.0341(15) Uani 1 1 d . . . . .
H8 H 0.800399 1.774833 0.349576 0.041 Uiso 1 1 calc R U . . .
C7 C 0.7876(3) 1.1602(4) 0.3438(5) 0.0268(10) Uani 1 1 d . . . . .
H7 H 0.809597 1.060864 0.344439 0.032 Uiso 1 1 calc R U . . .
C6 C 0.8482(2) 1.2800(4) 0.3414(6) 0.0254(9) Uani 1 1 d . . . . .
H6 H 0.910053 1.262874 0.337294 0.031 Uiso 1 1 calc R U . . .
C5 C 0.8131(2) 1.4280(4) 0.3454(4) 0.0187(8) Uani 1 1 d . . . . .
C9 C 0.4978(3) 0.6991(6) 0.4801(3) 0.0208(10) Uani 1 1 d . . . . .
C10 C 0.4985(3) 0.5680(6) 0.5429(3) 0.0222(10) Uani 1 1 d . . . . .
C11 C 0.5037(4) 0.5919(6) 0.6375(3) 0.0256(12) Uani 1 1 d . . . . .
H11 H 0.506230 0.690910 0.659777 0.031 Uiso 1 1 calc R U . . .
C12 C 0.5049(4) 0.4709(5) 0.6968(4) 0.0271(11) Uani 1 1 d . . . . .
H12 H 0.509204 0.487246 0.758675 0.032 Uiso 1 1 calc R U . . .
C13 C 0.4997(3) 0.3242(6) 0.6621(3) 0.0197(10) Uani 1 1 d . . . . .
C14 C 0.4951(3) 0.3011(5) 0.5689(3) 0.0209(9) Uani 1 1 d . . . . .
C15 C 0.4930(4) 0.4218(6) 0.5078(3) 0.0226(10) Uani 1 1 d . . . . .
H15 H 0.488048 0.404990 0.446000 0.027 Uiso 1 1 calc R U . . .
C16 C 0.4964(4) 0.0822(6) 0.6389(4) 0.0299(13) Uani 1 1 d . . . . .
H16 H 0.495945 -0.022558 0.648522 0.036 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 1.992(3) . ?
Co1 O2 1.996(4) . ?
Co1 N3 2.048(8) 3_475 ?
Co1 N1 2.048(7) 2_664 ?
N1 C16 1.319(8) . ?
N1 C13 1.384(8) . ?
C1 O3 1.244(6) . ?
C1 O1 1.292(5) . ?
C1 C2 1.496(5) . ?
O2 C9 1.267(6) . ?
N2 C8 1.350(5) . ?
N2 C4 1.384(5) . ?
N2 H2 0.8600 . ?
C2 C3 1.387(5) . ?
C2 C7 1.394(5) . ?
O4 C9 1.233(7) . ?
C4 C3 1.381(5) . ?
C4 C5 1.391(5) . ?
N4 C16 1.338(7) . ?
N4 C14 1.369(6) . ?
N4 H4 0.8600 . ?
C3 H3 0.9300 . ?
N3 C8 1.304(7) . ?
N3 C5 1.400(7) . ?
C8 H8 0.9300 . ?
C7 C6 1.382(5) . ?
C7 H7 0.9300 . ?
C6 C5 1.399(5) . ?
C6 H6 0.9300 . ?
C9 C10 1.479(7) . ?
C10 C15 1.386(8) . ?
C10 C11 1.418(7) . ?
C11 C12 1.378(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.388(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.398(6) . ?
C14 C15 1.393(7) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Co1 O2 134.70(13) . . ?
O1 Co1 N3 100.66(19) . 3_475 ?
O2 Co1 N3 107.70(19) . 3_475 ?
O1 Co1 N1 108.32(17) . 2_664 ?
O2 Co1 N1 100.73(19) . 2_664 ?
N3 Co1 N1 100.1(2) 3_475 2_664 ?
C16 N1 C13 105.3(6) . . ?
C16 N1 Co1 123.1(5) . 2_665 ?
C13 N1 Co1 131.5(4) . 2_665 ?
O3 C1 O1 120.9(5) . . ?
O3 C1 C2 121.5(4) . . ?
O1 C1 C2 117.6(3) . . ?
C1 O1 Co1 102.5(2) . . ?
C9 O2 Co1 104.2(3) . . ?
C8 N2 C4 106.9(3) . . ?
C8 N2 H2 126.5 . . ?
C4 N2 H2 126.5 . . ?
C3 C2 C7 120.7(3) . . ?
C3 C2 C1 118.8(3) . . ?
C7 C2 C1 120.5(3) . . ?
C3 C4 N2 131.6(3) . . ?
C3 C4 C5 122.9(3) . . ?
N2 C4 C5 105.5(3) . . ?
C16 N4 C14 107.3(4) . . ?
C16 N4 H4 126.3 . . ?
C14 N4 H4 126.3 . . ?
C4 C3 C2 117.0(3) . . ?
C4 C3 H3 121.5 . . ?
C2 C3 H3 121.5 . . ?
C8 N3 C5 105.2(6) . . ?
C8 N3 Co1 124.4(5) . 3_575 ?
C5 N3 Co1 130.4(4) . 3_575 ?
N3 C8 N2 113.3(5) . . ?
N3 C8 H8 123.4 . . ?
N2 C8 H8 123.4 . . ?
C6 C7 C2 122.0(3) . . ?
C6 C7 H7 119.0 . . ?
C2 C7 H7 119.0 . . ?
C7 C6 C5 117.6(3) . . ?
C7 C6 H6 121.2 . . ?
C5 C6 H6 121.2 . . ?
C4 C5 C6 119.7(3) . . ?
C4 C5 N3 109.1(4) . . ?
C6 C5 N3 131.2(4) . . ?
O4 C9 O2 120.0(6) . . ?
O4 C9 C10 122.0(5) . . ?
O2 C9 C10 118.0(4) . . ?
C15 C10 C11 120.7(4) . . ?
C15 C10 C9 118.8(4) . . ?
C11 C10 C9 120.5(4) . . ?
C12 C11 C10 121.1(4) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 118.5(5) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 H12 120.8 . . ?
N1 C13 C12 131.1(5) . . ?
N1 C13 C14 108.7(4) . . ?
C12 C13 C14 120.2(4) . . ?
N4 C14 C15 132.0(5) . . ?
N4 C14 C13 105.8(4) . . ?
C15 C14 C13 122.2(4) . . ?
C10 C15 C14 117.2(4) . . ?
C10 C15 H15 121.4 . . ?
C14 C15 H15 121.4 . . ?
N1 C16 N4 112.9(5) . . ?
N1 C16 H16 123.6 . . ?
N4 C16 H16 123.6 . . ?

_refine_diff_density_max         0.806
_refine_diff_density_min         -0.602
_refine_diff_density_rms         0.080



