# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_L
_database_code_depnum_ccdc_archive 'CCDC 1842662'
_audit_update_record             
;
2018-05-11 deposited with the CCDC.	2019-10-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H16 N6'
_chemical_formula_weight         388.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.252(6)
_cell_length_b                   10.732(7)
_cell_length_c                   9.599(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.160(11)
_cell_angle_gamma                90
_cell_volume                     950.5(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_F_000             404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.085
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5816
_diffrn_reflns_av_unetI/netI     0.0592
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.851
_diffrn_reflns_theta_max         28.352
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2318
_reflns_number_gt                1459
_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-2016/6 (Sheldrick, 2016)'
_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)+(0.0581P)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         2318
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1248
_refine_ls_wR_factor_gt          0.1075
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_restrained_S_all      0.987
_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
N1 N 0.14272(14) 0.88868(12) 0.03777(14) 0.0305(3) Uani 1 1 d . . . . .
C3 C 0.17248(17) 0.79016(15) 0.12083(16) 0.0298(4) Uani 1 1 d . . . . .
N2 N 0.39588(14) 0.74697(12) 0.00230(14) 0.0343(4) Uani 1 1 d . . . . .
H2 H 0.372970 0.789717 -0.071818 0.041 Uiso 1 1 calc R U . . .
C2 C 0.01342(17) 0.94426(14) 0.04535(17) 0.0301(4) Uani 1 1 d . . . . .
N3 N 0.37978(15) 0.66415(13) 0.21372(14) 0.0345(4) Uani 1 1 d . . . . .
C1 C -0.08856(18) 0.90277(16) 0.13330(19) 0.0386(4) Uani 1 1 d . . . . .
H1 H -0.176975 0.943508 0.136536 0.046 Uiso 1 1 calc R U . . .
C7 C 0.52054(18) 0.67951(15) 0.02968(18) 0.0325(4) Uani 1 1 d . . . . .
C6 C 0.31576(17) 0.73372(15) 0.11358(16) 0.0309(4) Uani 1 1 d . . . . .
C8 C 0.63741(19) 0.65501(17) -0.04934(19) 0.0416(5) Uani 1 1 d . . . . .
H8 H 0.642603 0.687734 -0.138551 0.050 Uiso 1 1 calc R U . . .
C4 C 0.07599(19) 0.74286(16) 0.21095(18) 0.0384(4) Uani 1 1 d . . . . .
H4 H 0.100244 0.674091 0.266790 0.046 Uiso 1 1 calc R U . . .
C11 C 0.62120(19) 0.55399(16) 0.22209(19) 0.0417(5) Uani 1 1 d . . . . .
H11 H 0.617023 0.521030 0.311316 0.050 Uiso 1 1 calc R U . . .
C5 C -0.0567(2) 0.79998(17) 0.2160(2) 0.0426(5) Uani 1 1 d . . . . .
H5 H -0.124192 0.769523 0.274626 0.051 Uiso 1 1 calc R U . . .
C12 C 0.50994(18) 0.62818(15) 0.16236(18) 0.0327(4) Uani 1 1 d . . . . .
C10 C 0.7374(2) 0.53122(18) 0.1445(2) 0.0462(5) Uani 1 1 d . . . . .
H10 H 0.813133 0.481899 0.182190 0.055 Uiso 1 1 calc R U . . .
C9 C 0.74471(19) 0.58012(18) 0.0109(2) 0.0451(5) Uani 1 1 d . . . . .
H9 H 0.824516 0.561524 -0.038902 0.054 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
N1 C3 1.341(2) . ?
N1 C2 1.343(2) . ?
C3 C4 1.384(2) . ?
C3 C6 1.464(2) . ?
N2 C6 1.351(2) . ?
N2 C7 1.371(2) . ?
C2 C1 1.384(2) . ?
C2 C2 1.490(3) 3_575 ?
N3 C6 1.323(2) . ?
N3 C12 1.389(2) . ?
C1 C5 1.378(2) . ?
C7 C8 1.390(2) . ?
C7 C12 1.398(2) . ?
C8 C9 1.372(2) . ?
C4 C5 1.376(2) . ?
C11 C10 1.374(3) . ?
C11 C12 1.392(2) . ?
C10 C9 1.392(3) . ?

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
C3 N1 C2 117.59(14) . . ?
N1 C3 C4 123.17(15) . . ?
N1 C3 C6 116.47(14) . . ?
C4 C3 C6 120.36(16) . . ?
C6 N2 C7 107.16(14) . . ?
N1 C2 C1 122.63(15) . . ?
N1 C2 C2 115.86(17) . 3_575 ?
C1 C2 C2 121.51(18) . 3_575 ?
C6 N3 C12 104.66(14) . . ?
C5 C1 C2 118.79(16) . . ?
N2 C7 C8 132.23(16) . . ?
N2 C7 C12 105.62(14) . . ?
C8 C7 C12 122.10(16) . . ?
N3 C6 N2 113.04(15) . . ?
N3 C6 C3 123.95(15) . . ?
N2 C6 C3 123.00(15) . . ?
C9 C8 C7 116.64(17) . . ?
C5 C4 C3 118.43(17) . . ?
C10 C11 C12 117.59(17) . . ?
C4 C5 C1 119.38(16) . . ?
N3 C12 C11 130.35(16) . . ?
N3 C12 C7 109.51(15) . . ?
C11 C12 C7 120.15(16) . . ?
C11 C10 C9 121.64(17) . . ?
C8 C9 C10 121.83(17) . . ?

_refine_diff_density_max         0.166
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_CdL
_database_code_depnum_ccdc_archive 'CCDC 1842664'
_audit_update_record             
;
2018-05-11 deposited with the CCDC.	2019-10-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H20 Cd N6 O3'
_chemical_formula_weight         576.88

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'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.2364(14)
_cell_length_b                   14.349(3)
_cell_length_c                   21.720(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.449(4)
_cell_angle_gamma                90
_cell_volume                     2241.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.710
_exptl_crystal_F_000             1160
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.019
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13956
_diffrn_reflns_av_unetI/netI     0.1165
_diffrn_reflns_av_R_equivalents  0.0829
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.704
_diffrn_reflns_theta_max         28.380
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5435
_reflns_number_gt                3060
_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-2016/6 (Sheldrick, 2016)'
_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)+(0.0411P)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         5435
_refine_ls_number_parameters     326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1150
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1186
_refine_ls_wR_factor_gt          0.0972
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_restrained_S_all      0.939
_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
Cd1 Cd 0.46806(5) 0.59299(3) 0.21901(2) 0.02947(13) Uani 1 1 d . . . . .
N5 N 0.4519(6) 0.9005(3) 0.2501(2) 0.0329(10) Uani 1 1 d . . . . .
C20 C 0.4928(7) 0.9105(4) 0.1897(2) 0.0317(12) Uani 1 1 d . . . . .
O2 O 0.1206(5) 0.5621(2) 0.18534(18) 0.0405(10) Uani 1 1 d . . . . .
C18 C 0.3911(7) 0.7633(4) 0.3170(2) 0.0311(13) Uani 1 1 d . . . . .
O1 O 0.3055(5) 0.6039(3) 0.11652(17) 0.0430(10) Uani 1 1 d . . . . .
C2 C 0.5847(7) 0.3968(4) 0.1412(2) 0.0307(12) Uani 1 1 d . . . . .
N1 N 0.4087(6) 0.6695(3) 0.3170(2) 0.0301(10) Uani 1 1 d . . . . .
C19 C 0.4278(7) 0.8067(4) 0.2581(2) 0.0286(12) Uani 1 1 d . . . . .
C1 C 0.1494(8) 0.5820(3) 0.1312(3) 0.0326(13) Uani 1 1 d . . . . .
C25 C 0.4903(7) 0.8194(4) 0.1638(3) 0.0319(13) Uani 1 1 d . . . . .
N6 N 0.4494(6) 0.7570(3) 0.20862(19) 0.0291(10) Uani 1 1 d . . . . .
N2 N 0.4672(6) 0.4908(3) 0.30856(19) 0.0282(10) Uani 1 1 d . . . . .
N3 N 0.6012(6) 0.2932(3) 0.2197(2) 0.0336(11) Uani 1 1 d . . . . .
H3 H 0.615577 0.243449 0.241795 0.040 Uiso 1 1 calc R U . . .
C9 C 0.5073(7) 0.4008(4) 0.2994(2) 0.0301(12) Uani 1 1 d . . . . .
N4 N 0.5388(6) 0.4442(3) 0.19227(19) 0.0298(10) Uani 1 1 d . . . . .
C14 C 0.3871(7) 0.6218(3) 0.3682(2) 0.0287(12) Uani 1 1 d . . . . .
C13 C 0.4234(7) 0.5196(4) 0.3635(2) 0.0287(12) Uani 1 1 d . . . . .
C7 C 0.6239(7) 0.3041(4) 0.1585(2) 0.0301(12) Uani 1 1 d . . . . .
C11 C 0.4506(8) 0.3644(4) 0.4025(3) 0.0417(15) Uani 1 1 d . . . . .
H11 H 0.443473 0.321470 0.434252 0.050 Uiso 1 1 calc R U . . .
C21 C 0.5321(8) 0.9879(4) 0.1554(3) 0.0408(15) Uani 1 1 d . . . . .
H21 H 0.536392 1.047326 0.172537 0.049 Uiso 1 1 calc R U . . .
O3 O 0.7837(5) 0.6291(2) 0.22272(19) 0.0475(11) Uani 1 1 d . . . . .
H3A H 0.799077 0.686956 0.230103 0.071 Uiso 1 1 d R U . . .
H3B H 0.817927 0.621646 0.186883 0.071 Uiso 1 1 d R U . . .
C12 C 0.4139(7) 0.4575(4) 0.4124(3) 0.0363(14) Uani 1 1 d . . . . .
H12 H 0.383707 0.478086 0.450670 0.044 Uiso 1 1 calc R U . . .
C8 C 0.5508(7) 0.3789(3) 0.2375(2) 0.0281(12) Uani 1 1 d . . . . .
C15 C 0.3405(8) 0.6656(4) 0.4215(3) 0.0370(14) Uani 1 1 d . . . . .
H15 H 0.325455 0.631371 0.456926 0.044 Uiso 1 1 calc R U . . .
C6 C 0.6738(7) 0.2395(4) 0.1145(3) 0.0360(14) Uani 1 1 d . . . . .
H6 H 0.702199 0.178092 0.125487 0.043 Uiso 1 1 calc R U . . .
C4 C 0.6383(8) 0.3626(4) 0.0378(3) 0.0464(16) Uani 1 1 d . . . . .
H4 H 0.644110 0.380959 -0.002957 0.056 Uiso 1 1 calc R U . . .
C17 C 0.3442(8) 0.8121(4) 0.3682(3) 0.0378(14) Uani 1 1 d . . . . .
H17 H 0.331416 0.876633 0.367341 0.045 Uiso 1 1 calc R U . . .
C10 C 0.4973(8) 0.3353(4) 0.3466(3) 0.0356(14) Uani 1 1 d . . . . .
H10 H 0.522031 0.272723 0.339833 0.043 Uiso 1 1 calc R U . . .
C16 C 0.3171(8) 0.7613(4) 0.4203(3) 0.0427(15) Uani 1 1 d . . . . .
H16 H 0.282791 0.791691 0.455130 0.051 Uiso 1 1 calc R U . . .
C5 C 0.6794(8) 0.2697(4) 0.0549(3) 0.0430(15) Uani 1 1 d . . . . .
H5 H 0.711172 0.227903 0.025140 0.052 Uiso 1 1 calc R U . . .
C24 C 0.5224(7) 0.8063(4) 0.1028(2) 0.0370(14) Uani 1 1 d . . . . .
H24 H 0.519068 0.747001 0.085400 0.044 Uiso 1 1 calc R U . . .
C23 C 0.5595(8) 0.8834(4) 0.0688(3) 0.0419(15) Uani 1 1 d . . . . .
H23 H 0.581737 0.876039 0.027700 0.050 Uiso 1 1 calc R U . . .
C22 C 0.5646(8) 0.9731(4) 0.0948(3) 0.0436(15) Uani 1 1 d . . . . .
H22 H 0.590513 1.023897 0.070612 0.052 Uiso 1 1 calc R U . . .
C3 C 0.5893(8) 0.4269(4) 0.0804(3) 0.0399(14) Uani 1 1 d . . . . .
H3C H 0.560508 0.488115 0.068853 0.048 Uiso 1 1 calc R U . . .
C26 C -0.0117(9) 0.5817(5) 0.0805(3) 0.069(2) Uani 1 1 d . . . . .
H26A H -0.092335 0.633336 0.086218 0.103 Uiso 1 1 calc R U . . .
H26B H -0.079823 0.524493 0.082026 0.103 Uiso 1 1 calc R U . . .
H26C H 0.034713 0.587084 0.040906 0.103 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
Cd1 N4 2.285(4) . ?
Cd1 O3 2.334(4) . ?
Cd1 N6 2.366(4) . ?
Cd1 O1 2.403(4) . ?
Cd1 N2 2.437(4) . ?
Cd1 N1 2.475(4) . ?
Cd1 O2 2.577(4) . ?
N5 C19 1.370(6) . ?
N5 C20 1.384(6) . ?
C20 C21 1.384(7) . ?
C20 C25 1.423(7) . ?
O2 C1 1.250(6) . ?
C18 N1 1.353(6) . ?
C18 C17 1.387(7) . ?
C18 C19 1.474(7) . ?
O1 C1 1.248(6) . ?
C2 N4 1.373(6) . ?
C2 C3 1.395(7) . ?
C2 C7 1.403(7) . ?
N1 C14 1.330(6) . ?
C19 N6 1.315(6) . ?
C1 C26 1.512(8) . ?
C25 N6 1.379(6) . ?
C25 C24 1.382(7) . ?
N2 C13 1.334(6) . ?
N2 C9 1.343(6) . ?
N3 C8 1.351(6) . ?
N3 C7 1.367(6) . ?
C9 C10 1.399(7) . ?
C9 C8 1.449(7) . ?
N4 C8 1.354(6) . ?
C14 C15 1.390(7) . ?
C14 C13 1.496(7) . ?
C13 C12 1.395(7) . ?
C7 C6 1.408(7) . ?
C11 C10 1.364(7) . ?
C11 C12 1.383(7) . ?
C21 C22 1.378(8) . ?
C15 C16 1.384(7) . ?
C6 C5 1.368(7) . ?
C4 C3 1.380(7) . ?
C4 C5 1.406(8) . ?
C17 C16 1.380(7) . ?
C24 C23 1.374(7) . ?
C23 C22 1.406(8) . ?

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
N4 Cd1 O3 88.29(14) . . ?
N4 Cd1 N6 156.44(15) . . ?
O3 Cd1 N6 80.08(13) . . ?
N4 Cd1 O1 85.76(14) . . ?
O3 Cd1 O1 113.13(14) . . ?
N6 Cd1 O1 80.20(13) . . ?
N4 Cd1 N2 70.21(15) . . ?
O3 Cd1 N2 101.32(14) . . ?
N6 Cd1 N2 132.02(14) . . ?
O1 Cd1 N2 137.22(13) . . ?
N4 Cd1 N1 134.28(14) . . ?
O3 Cd1 N1 97.79(13) . . ?
N6 Cd1 N1 68.13(14) . . ?
O1 Cd1 N1 130.80(13) . . ?
N2 Cd1 N1 64.16(14) . . ?
N4 Cd1 O2 90.38(14) . . ?
O3 Cd1 O2 165.38(13) . . ?
N6 Cd1 O2 95.75(13) . . ?
O1 Cd1 O2 52.25(12) . . ?
N2 Cd1 O2 91.91(13) . . ?
N1 Cd1 O2 93.56(13) . . ?
C19 N5 C20 105.4(4) . . ?
N5 C20 C21 132.2(5) . . ?
N5 C20 C25 106.6(5) . . ?
C21 C20 C25 121.2(5) . . ?
C1 O2 Cd1 88.1(3) . . ?
N1 C18 C17 122.3(5) . . ?
N1 C18 C19 113.2(5) . . ?
C17 C18 C19 124.5(5) . . ?
C1 O1 Cd1 96.3(3) . . ?
N4 C2 C3 130.2(5) . . ?
N4 C2 C7 108.3(5) . . ?
C3 C2 C7 121.5(5) . . ?
C14 N1 C18 119.4(4) . . ?
C14 N1 Cd1 122.7(3) . . ?
C18 N1 Cd1 117.9(3) . . ?
N6 C19 N5 113.6(5) . . ?
N6 C19 C18 122.0(5) . . ?
N5 C19 C18 124.3(5) . . ?
O1 C1 O2 123.3(5) . . ?
O1 C1 C26 117.4(5) . . ?
O2 C1 C26 119.3(6) . . ?
N6 C25 C24 131.3(5) . . ?
N6 C25 C20 108.1(5) . . ?
C24 C25 C20 120.5(5) . . ?
C19 N6 C25 106.2(4) . . ?
C19 N6 Cd1 118.2(3) . . ?
C25 N6 Cd1 134.3(3) . . ?
C13 N2 C9 120.5(4) . . ?
C13 N2 Cd1 123.3(3) . . ?
C9 N2 Cd1 116.1(3) . . ?
C8 N3 C7 103.9(4) . . ?
N2 C9 C10 120.5(5) . . ?
N2 C9 C8 114.8(4) . . ?
C10 C9 C8 124.6(5) . . ?
C8 N4 C2 104.0(4) . . ?
C8 N4 Cd1 117.4(3) . . ?
C2 N4 Cd1 138.5(3) . . ?
N1 C14 C15 121.7(5) . . ?
N1 C14 C13 114.1(4) . . ?
C15 C14 C13 124.1(5) . . ?
N2 C13 C12 121.4(5) . . ?
N2 C13 C14 115.3(4) . . ?
C12 C13 C14 123.4(5) . . ?
N3 C7 C2 109.0(5) . . ?
N3 C7 C6 130.9(5) . . ?
C2 C7 C6 120.1(5) . . ?
C10 C11 C12 120.4(5) . . ?
C22 C21 C20 117.3(5) . . ?
C11 C12 C13 118.1(5) . . ?
N3 C8 N4 114.8(5) . . ?
N3 C8 C9 123.8(5) . . ?
N4 C8 C9 121.3(4) . . ?
C16 C15 C14 118.3(5) . . ?
C5 C6 C7 118.1(5) . . ?
C3 C4 C5 121.3(6) . . ?
C16 C17 C18 117.4(5) . . ?
C11 C10 C9 119.0(5) . . ?
C17 C16 C15 120.7(5) . . ?
C6 C5 C4 121.5(5) . . ?
C23 C24 C25 118.0(5) . . ?
C24 C23 C22 121.2(6) . . ?
C21 C22 C23 121.7(6) . . ?
C4 C3 C2 117.5(5) . . ?

_refine_diff_density_max         0.682
_refine_diff_density_min         -0.622
_refine_diff_density_rms         0.124

####################################################################### 
# 
# 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_NiL
_database_code_depnum_ccdc_archive 'CCDC 1842665'
_audit_update_record             
;
2018-05-11 deposited with the CCDC.	2019-10-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 N8 Ni O8'
_chemical_formula_weight         607.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3390 1.1120 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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                   14.948(10)
_cell_length_b                   10.773(8)
_cell_length_c                   15.691(11)
_cell_angle_alpha                90
_cell_angle_beta                 98.987(12)
_cell_angle_gamma                90
_cell_volume                     2496(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.845
_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      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10658
_diffrn_reflns_av_unetI/netI     0.0967
_diffrn_reflns_av_R_equivalents  0.0706
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.379
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.960
_reflns_number_total             4469
_reflns_number_gt                3093
_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 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.1230P)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         4469
_refine_ls_number_parameters     372
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1189
_refine_ls_R_factor_gt           0.0879
_refine_ls_wR_factor_ref         0.2441
_refine_ls_wR_factor_gt          0.2225
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_restrained_S_all      1.140
_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
Ni1 Ni 0.25289(5) 0.58736(6) 0.24148(5) 0.0262(3) Uani 1 1 d . . . . .
O1 O 0.1329(3) 0.6223(4) 0.2894(3) 0.0388(10) Uani 1 1 d . . . . .
H1A H 0.126108 0.704041 0.296709 0.058 Uiso 1 1 d R U . . .
H1B H 0.135061 0.592366 0.342963 0.058 Uiso 1 1 d R U . . .
O2 O 0.3705(3) 0.5303(4) 0.1948(3) 0.0368(10) Uani 1 1 d . . . . .
H2A H 0.408291 0.479531 0.233174 0.055 Uiso 1 1 d R U . . .
H2B H 0.409509 0.596250 0.188652 0.055 Uiso 1 1 d R U . . .
N1 N 0.3107(3) 0.5149(4) 0.3649(3) 0.0299(11) Uani 1 1 d . . . . .
N3 N 0.3136(3) 0.7414(4) 0.3022(3) 0.0281(10) Uani 1 1 d . . . . .
N4 N 0.2316(3) 0.7242(4) 0.1505(3) 0.0299(11) Uani 1 1 d . . . . .
N5 N 0.1750(3) 0.4914(4) 0.1342(3) 0.0302(11) Uani 1 1 d . . . . .
N2 N 0.3966(3) 0.5587(5) 0.4908(3) 0.0374(13) Uani 1 1 d . . . . .
H2 H 0.431110 0.601149 0.531260 0.045 Uiso 1 1 calc R U . . .
N6 N 0.1215(3) 0.5059(5) -0.0066(3) 0.0329(11) Uani 1 1 d . . . . .
H6 H 0.108169 0.538588 -0.058409 0.039 Uiso 1 1 calc R U . . .
C1 C 0.3561(4) 0.6021(5) 0.4129(4) 0.0281(12) Uani 1 1 d . . . . .
C12 C 0.1636(4) 0.5655(5) 0.0654(4) 0.0300(13) Uani 1 1 d . . . . .
C10 C 0.2582(4) 0.8385(5) 0.1721(4) 0.0273(12) Uani 1 1 d . . . . .
C11 C 0.1858(4) 0.6950(5) 0.0709(4) 0.0283(13) Uani 1 1 d . . . . .
C9 C 0.3100(4) 0.8478(5) 0.2601(4) 0.0289(13) Uani 1 1 d . . . . .
C3 C 0.3204(4) 0.4061(5) 0.4145(4) 0.0335(14) Uani 1 1 d . . . . .
C8 C 0.3610(4) 0.7292(5) 0.3821(4) 0.0316(13) Uani 1 1 d . . . . .
C2 C 0.3733(4) 0.4366(6) 0.4940(4) 0.0324(14) Uani 1 1 d . . . . .
C19 C 0.1678(4) 0.7850(5) 0.0091(4) 0.0337(14) Uani 1 1 d . . . . .
H19 H 0.138781 0.765073 -0.047498 0.040 Uiso 1 1 calc R U . . .
C14 C 0.1034(4) 0.3860(6) 0.0155(4) 0.0328(14) Uani 1 1 d . . . . .
C13 C 0.1365(4) 0.3790(6) 0.1052(4) 0.0341(14) Uani 1 1 d . . . . .
C21 C 0.2374(4) 0.9362(5) 0.1121(4) 0.0328(14) Uani 1 1 d . . . . .
H21 H 0.253848 1.019363 0.127560 0.039 Uiso 1 1 calc R U . . .
C22 C 0.3530(4) 0.9534(6) 0.2982(4) 0.0403(16) Uani 1 1 d . . . . .
H22 H 0.349244 1.030609 0.268628 0.048 Uiso 1 1 calc R U . . .
C24 C 0.4058(4) 0.8289(6) 0.4241(4) 0.0403(15) Uani 1 1 d . . . . .
H24 H 0.438661 0.820869 0.480769 0.048 Uiso 1 1 calc R U . . .
C4 C 0.2857(4) 0.2901(5) 0.3965(4) 0.0390(15) Uani 1 1 d . . . . .
H4 H 0.250482 0.270466 0.342440 0.047 Uiso 1 1 calc R U . . .
C20 C 0.1933(4) 0.9085(5) 0.0317(4) 0.0361(15) Uani 1 1 d . . . . .
H20 H 0.179592 0.972901 -0.009625 0.043 Uiso 1 1 calc R U . . .
C18 C 0.1248(5) 0.2705(6) 0.1502(4) 0.0422(16) Uani 1 1 d . . . . .
H18 H 0.143465 0.265483 0.210864 0.051 Uiso 1 1 calc R U . . .
C23 C 0.4012(5) 0.9422(6) 0.3802(5) 0.0454(17) Uani 1 1 d . . . . .
H23 H 0.431773 1.012464 0.407348 0.054 Uiso 1 1 calc R U . . .
C17 C 0.0853(5) 0.1705(7) 0.1043(5) 0.0513(18) Uani 1 1 d . . . . .
H17 H 0.079353 0.094113 0.133093 0.062 Uiso 1 1 calc R U . . .
C16 C 0.0534(4) 0.1799(6) 0.0143(5) 0.0439(16) Uani 1 1 d . . . . .
H16 H 0.024608 0.110617 -0.015876 0.053 Uiso 1 1 calc R U . . .
C7 C 0.3910(5) 0.3443(6) 0.5589(5) 0.0439(17) Uani 1 1 d . . . . .
H7 H 0.426424 0.361999 0.613243 0.053 Uiso 1 1 calc R U . . .
C15 C 0.0638(4) 0.2873(6) -0.0292(5) 0.0433(16) Uani 1 1 d . . . . .
H15 H 0.043709 0.292921 -0.089629 0.052 Uiso 1 1 calc R U . . .
C5 C 0.3049(5) 0.2016(7) 0.4625(5) 0.0504(18) Uani 1 1 d . . . . .
H5 H 0.282033 0.119702 0.452830 0.061 Uiso 1 1 calc R U . . .
C6 C 0.3555(5) 0.2300(7) 0.5403(5) 0.052(2) Uani 1 1 d . . . . .
H6A H 0.366281 0.167050 0.583111 0.062 Uiso 1 1 calc R U . . .
O3 O -0.1127(3) 0.3695(4) 0.1708(3) 0.0510(13) Uani 1 1 d . . . . .
O4 O -0.0263(4) 0.5276(5) 0.2004(4) 0.0665(16) Uani 1 1 d . . . . .
O5 O -0.0250(5) 0.3830(6) 0.2940(4) 0.0759(18) Uani 1 1 d . . . . .
N7 N -0.0537(4) 0.4253(5) 0.2240(4) 0.0403(13) Uani 1 1 d . . . . .
O6 O 0.4961(4) 0.4108(4) 0.3299(4) 0.0561(14) Uani 1 1 d . . . . .
O7 O 0.5470(4) 0.2335(5) 0.3747(3) 0.0604(14) Uani 1 1 d . . . . .
O8 O 0.4571(5) 0.2488(6) 0.2546(3) 0.090(2) Uani 1 1 d . . . . .
N8 N 0.4979(3) 0.2989(5) 0.3188(3) 0.0404(13) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 N4 2.042(5) . ?
Ni1 N3 2.053(5) . ?
Ni1 O1 2.084(4) . ?
Ni1 O2 2.099(4) . ?
Ni1 N1 2.141(5) . ?
Ni1 N5 2.155(5) . ?
N1 C1 1.322(7) . ?
N1 C3 1.402(7) . ?
N3 C9 1.320(7) . ?
N3 C8 1.347(7) . ?
N4 C10 1.323(7) . ?
N4 C11 1.363(7) . ?
N5 C12 1.332(8) . ?
N5 C13 1.386(8) . ?
N2 C1 1.360(8) . ?
N2 C2 1.364(8) . ?
N6 C12 1.365(8) . ?
N6 C14 1.375(8) . ?
C1 C8 1.459(8) . ?
C12 C11 1.434(8) . ?
C10 C21 1.414(8) . ?
C10 C9 1.476(8) . ?
C11 C19 1.368(8) . ?
C9 C22 1.395(9) . ?
C3 C4 1.365(9) . ?
C3 C2 1.408(9) . ?
C8 C24 1.378(8) . ?
C2 C7 1.418(9) . ?
C19 C20 1.414(8) . ?
C14 C15 1.358(9) . ?
C14 C13 1.418(9) . ?
C13 C18 1.392(8) . ?
C21 C20 1.362(9) . ?
C22 C23 1.378(10) . ?
C24 C23 1.397(10) . ?
C4 C5 1.404(9) . ?
C18 C17 1.377(10) . ?
C17 C16 1.422(10) . ?
C16 C15 1.365(10) . ?
C7 C6 1.355(10) . ?
C5 C6 1.367(10) . ?
O3 N7 1.268(7) . ?
O4 N7 1.252(7) . ?
O5 N7 1.204(8) . ?
O6 N8 1.218(7) . ?
O7 N8 1.266(7) . ?
O8 N8 1.219(7) . ?

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
N4 Ni1 N3 75.54(19) . . ?
N4 Ni1 O1 94.17(19) . . ?
N3 Ni1 O1 91.69(18) . . ?
N4 Ni1 O2 90.87(18) . . ?
N3 Ni1 O2 93.72(18) . . ?
O1 Ni1 O2 173.38(17) . . ?
N4 Ni1 N1 153.18(19) . . ?
N3 Ni1 N1 77.78(19) . . ?
O1 Ni1 N1 89.30(18) . . ?
O2 Ni1 N1 88.12(18) . . ?
N4 Ni1 N5 78.10(19) . . ?
N3 Ni1 N5 153.60(19) . . ?
O1 Ni1 N5 88.76(18) . . ?
O2 Ni1 N5 88.08(18) . . ?
N1 Ni1 N5 128.62(19) . . ?
C1 N1 C3 106.2(5) . . ?
C1 N1 Ni1 110.8(4) . . ?
C3 N1 Ni1 143.0(4) . . ?
C9 N3 C8 121.7(5) . . ?
C9 N3 Ni1 119.3(4) . . ?
C8 N3 Ni1 118.9(4) . . ?
C10 N4 C11 122.5(5) . . ?
C10 N4 Ni1 119.0(4) . . ?
C11 N4 Ni1 118.4(4) . . ?
C12 N5 C13 105.3(5) . . ?
C12 N5 Ni1 109.3(4) . . ?
C13 N5 Ni1 145.2(4) . . ?
C1 N2 C2 106.5(5) . . ?
C12 N6 C14 108.5(5) . . ?
N1 C1 N2 112.6(5) . . ?
N1 C1 C8 121.8(5) . . ?
N2 C1 C8 125.6(5) . . ?
N5 C12 N6 111.9(5) . . ?
N5 C12 C11 122.4(5) . . ?
N6 C12 C11 125.5(5) . . ?
N4 C10 C21 119.8(6) . . ?
N4 C10 C9 113.3(5) . . ?
C21 C10 C9 126.9(5) . . ?
N4 C11 C19 120.1(5) . . ?
N4 C11 C12 110.9(5) . . ?
C19 C11 C12 129.0(6) . . ?
N3 C9 C22 120.9(6) . . ?
N3 C9 C10 112.6(5) . . ?
C22 C9 C10 126.6(5) . . ?
C4 C3 N1 130.4(6) . . ?
C4 C3 C2 122.7(6) . . ?
N1 C3 C2 106.9(5) . . ?
N3 C8 C24 121.1(6) . . ?
N3 C8 C1 110.7(5) . . ?
C24 C8 C1 128.2(6) . . ?
N2 C2 C3 107.7(5) . . ?
N2 C2 C7 133.0(6) . . ?
C3 C2 C7 119.2(6) . . ?
C11 C19 C20 118.2(6) . . ?
C15 C14 N6 133.7(6) . . ?
C15 C14 C13 121.9(6) . . ?
N6 C14 C13 104.4(5) . . ?
N5 C13 C18 130.2(6) . . ?
N5 C13 C14 110.0(5) . . ?
C18 C13 C14 119.7(6) . . ?
C20 C21 C10 118.5(5) . . ?
C23 C22 C9 117.9(6) . . ?
C8 C24 C23 117.5(6) . . ?
C3 C4 C5 116.2(6) . . ?
C21 C20 C19 120.7(6) . . ?
C17 C18 C13 117.9(6) . . ?
C22 C23 C24 121.0(6) . . ?
C18 C17 C16 121.0(6) . . ?
C15 C16 C17 120.7(6) . . ?
C6 C7 C2 117.4(7) . . ?
C14 C15 C16 118.6(7) . . ?
C6 C5 C4 121.9(7) . . ?
C7 C6 C5 122.6(7) . . ?
O5 N7 O4 121.1(6) . . ?
O5 N7 O3 122.2(6) . . ?
O4 N7 O3 116.7(6) . . ?
O6 N8 O8 122.5(7) . . ?
O6 N8 O7 118.3(6) . . ?
O8 N8 O7 119.1(6) . . ?

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
C3 N1 C1 N2 0.9(6) . . . . ?
Ni1 N1 C1 N2 -177.8(4) . . . . ?
C3 N1 C1 C8 -179.9(5) . . . . ?
Ni1 N1 C1 C8 1.4(7) . . . . ?
C2 N2 C1 N1 -2.0(7) . . . . ?
C2 N2 C1 C8 178.8(5) . . . . ?
C13 N5 C12 N6 -1.3(7) . . . . ?
Ni1 N5 C12 N6 174.6(4) . . . . ?
C13 N5 C12 C11 173.2(5) . . . . ?
Ni1 N5 C12 C11 -10.9(7) . . . . ?
C14 N6 C12 N5 0.5(7) . . . . ?
C14 N6 C12 C11 -173.8(5) . . . . ?
C11 N4 C10 C21 1.5(8) . . . . ?
Ni1 N4 C10 C21 -174.8(4) . . . . ?
C11 N4 C10 C9 -177.5(5) . . . . ?
Ni1 N4 C10 C9 6.2(6) . . . . ?
C10 N4 C11 C19 1.6(8) . . . . ?
Ni1 N4 C11 C19 177.9(4) . . . . ?
C10 N4 C11 C12 -178.8(5) . . . . ?
Ni1 N4 C11 C12 -2.4(6) . . . . ?
N5 C12 C11 N4 9.3(8) . . . . ?
N6 C12 C11 N4 -176.9(5) . . . . ?
N5 C12 C11 C19 -171.1(6) . . . . ?
N6 C12 C11 C19 2.7(10) . . . . ?
C8 N3 C9 C22 -2.1(8) . . . . ?
Ni1 N3 C9 C22 -177.8(4) . . . . ?
C8 N3 C9 C10 177.1(5) . . . . ?
Ni1 N3 C9 C10 1.3(6) . . . . ?
N4 C10 C9 N3 -4.7(7) . . . . ?
C21 C10 C9 N3 176.3(5) . . . . ?
N4 C10 C9 C22 174.4(6) . . . . ?
C21 C10 C9 C22 -4.6(9) . . . . ?
C1 N1 C3 C4 178.4(6) . . . . ?
Ni1 N1 C3 C4 -3.6(11) . . . . ?
C1 N1 C3 C2 0.5(6) . . . . ?
Ni1 N1 C3 C2 178.5(5) . . . . ?
C9 N3 C8 C24 1.7(9) . . . . ?
Ni1 N3 C8 C24 177.5(5) . . . . ?
C9 N3 C8 C1 -178.4(5) . . . . ?
Ni1 N3 C8 C1 -2.7(6) . . . . ?
N1 C1 C8 N3 0.7(8) . . . . ?
N2 C1 C8 N3 179.8(5) . . . . ?
N1 C1 C8 C24 -179.5(6) . . . . ?
N2 C1 C8 C24 -0.4(10) . . . . ?
C1 N2 C2 C3 2.2(6) . . . . ?
C1 N2 C2 C7 -176.8(6) . . . . ?
C4 C3 C2 N2 -179.8(6) . . . . ?
N1 C3 C2 N2 -1.7(6) . . . . ?
C4 C3 C2 C7 -0.6(9) . . . . ?
N1 C3 C2 C7 177.5(5) . . . . ?
N4 C11 C19 C20 -3.4(8) . . . . ?
C12 C11 C19 C20 177.1(6) . . . . ?
C12 N6 C14 C15 -179.7(7) . . . . ?
C12 N6 C14 C13 0.6(6) . . . . ?
C12 N5 C13 C18 -176.1(7) . . . . ?
Ni1 N5 C13 C18 10.6(11) . . . . ?
C12 N5 C13 C14 1.7(6) . . . . ?
Ni1 N5 C13 C14 -171.6(5) . . . . ?
C15 C14 C13 N5 178.8(5) . . . . ?
N6 C14 C13 N5 -1.4(6) . . . . ?
C15 C14 C13 C18 -3.1(9) . . . . ?
N6 C14 C13 C18 176.7(5) . . . . ?
N4 C10 C21 C20 -2.7(8) . . . . ?
C9 C10 C21 C20 176.2(5) . . . . ?
N3 C9 C22 C23 1.6(9) . . . . ?
C10 C9 C22 C23 -177.4(6) . . . . ?
N3 C8 C24 C23 -0.9(9) . . . . ?
C1 C8 C24 C23 179.3(6) . . . . ?
N1 C3 C4 C5 -177.0(6) . . . . ?
C2 C3 C4 C5 0.6(9) . . . . ?
C10 C21 C20 C19 0.9(9) . . . . ?
C11 C19 C20 C21 2.1(9) . . . . ?
N5 C13 C18 C17 -178.8(6) . . . . ?
C14 C13 C18 C17 3.6(9) . . . . ?
C9 C22 C23 C24 -0.8(10) . . . . ?
C8 C24 C23 C22 0.4(10) . . . . ?
C13 C18 C17 C16 -3.1(10) . . . . ?
C18 C17 C16 C15 2.1(11) . . . . ?
N2 C2 C7 C6 179.0(6) . . . . ?
C3 C2 C7 C6 0.1(9) . . . . ?
N6 C14 C15 C16 -177.7(6) . . . . ?
C13 C14 C15 C16 2.0(9) . . . . ?
C17 C16 C15 C14 -1.5(10) . . . . ?
C3 C4 C5 C6 0.0(10) . . . . ?
C2 C7 C6 C5 0.4(10) . . . . ?
C4 C5 C6 C7 -0.5(11) . . . . ?

_refine_diff_density_max         1.122
_refine_diff_density_min         -0.729
_refine_diff_density_rms         0.168

####################################################################### 
# 
# 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_CoL
_database_code_depnum_ccdc_archive 'CCDC 1842663'
_audit_update_record             
;
2018-05-11 deposited with the CCDC.	2019-10-01 downloaded from the CCDC.
;
_audit_creation_date             2018-04-04
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.07.08 svn.r3312 for OlexSys, GUI svn.r5203)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H18 Co N6 O3'
_chemical_formula_sum            'C25 H18 Co N6 O3'
_chemical_formula_weight         509.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.3490 0.9720 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1558(8)
_cell_length_b                   11.4155(13)
_cell_length_c                   13.8516(15)
_cell_angle_alpha                70.245(2)
_cell_angle_beta                 81.521(2)
_cell_angle_gamma                82.789(2)
_cell_volume                     1049.8(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1200
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.788
_cell_measurement_theta_min      2.836
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.862
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  0.679947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.0368 before and 0.0252 after correction.
The Ratio of minimum to maximum transmission is 0.6799.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             522
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0789
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6611
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.172
_diffrn_reflns_theta_min         1.902
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3194
_reflns_number_total             4795
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.34A (Bruker, 200?)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.34A (Bruker, 200?)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.500
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4795
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0541
_refine_ls_restrained_S_all      0.974
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0652P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1402
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Riding coordinates:
 O3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C5(H5), C6(H6), C7(H7), C8(H8), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.75668(6) 0.53610(4) 0.73913(3) 0.02846(16) Uani 1 1 d . . . . .
O1 O 0.4636(3) 0.5955(2) 0.75935(18) 0.0392(6) Uani 1 1 d . . . . .
O3 O 1.0534(3) 0.4963(2) 0.73053(17) 0.0338(6) Uani 1 1 d . . . . .
H3A H 1.112261 0.569915 0.724473 0.051 Uiso 1 1 d R . . . .
H3B H 1.096921 0.470815 0.671143 0.051 Uiso 1 1 d R . . . .
O2 O 0.2124(4) 0.7158(3) 0.7057(2) 0.0519(7) Uani 1 1 d . . . . .
N1 N 0.7834(4) 0.5872(2) 0.8769(2) 0.0283(6) Uani 1 1 d . . . . .
N2 N 0.7480(4) 0.5270(2) 1.0496(2) 0.0280(6) Uani 1 1 d . . . . .
H2 H 0.725812 0.480388 1.112807 0.034 Uiso 1 1 calc R . . . .
N3 N 0.7041(4) 0.3702(3) 0.8679(2) 0.0280(6) Uani 1 1 d . . . . .
N4 N 0.7234(4) 0.3946(3) 0.6784(2) 0.0293(6) Uani 1 1 d . . . . .
N5 N 0.7724(4) 0.6307(3) 0.5784(2) 0.0317(7) Uani 1 1 d . . . . .
N6 N 0.7867(4) 0.6095(3) 0.4184(2) 0.0327(7) Uani 1 1 d . . . . .
C1 C 0.3842(5) 0.6884(4) 0.7069(3) 0.0375(9) Uani 1 1 d . . . . .
H1 H 0.461836 0.747469 0.661273 0.045 Uiso 1 1 calc R . . . .
C2 C 0.7449(4) 0.4945(3) 0.9642(2) 0.0256(7) Uani 1 1 d . . . . .
C3 C 0.7936(4) 0.6493(3) 1.0155(2) 0.0267(7) Uani 1 1 d . . . . .
C4 C 0.8152(4) 0.6854(3) 0.9079(2) 0.0270(7) Uani 1 1 d . . . . .
C5 C 0.8621(5) 0.8067(3) 0.8491(3) 0.0336(8) Uani 1 1 d . . . . .
H5 H 0.878292 0.832365 0.777362 0.040 Uiso 1 1 calc R . . . .
C6 C 0.8831(5) 0.8861(3) 0.9015(3) 0.0387(9) Uani 1 1 d . . . . .
H6 H 0.912908 0.967353 0.864378 0.046 Uiso 1 1 calc R . . . .
C7 C 0.8608(5) 0.8475(3) 1.0105(3) 0.0365(8) Uani 1 1 d . . . . .
H7 H 0.876232 0.904027 1.043275 0.044 Uiso 1 1 calc R . . . .
C8 C 0.8167(5) 0.7287(3) 1.0693(3) 0.0341(8) Uani 1 1 d . . . . .
H8 H 0.803101 0.702753 1.141057 0.041 Uiso 1 1 calc R . . . .
C9 C 0.7041(4) 0.3719(3) 0.9646(3) 0.0272(7) Uani 1 1 d . . . . .
C10 C 0.6745(4) 0.2655(3) 0.8519(3) 0.0289(7) Uani 1 1 d . . . . .
C11 C 0.6858(5) 0.2795(3) 0.7407(3) 0.0309(8) Uani 1 1 d . . . . .
C12 C 0.7379(5) 0.4228(3) 0.5757(3) 0.0303(8) Uani 1 1 d . . . . .
C13 C 0.7688(5) 0.5562(3) 0.5212(2) 0.0284(7) Uani 1 1 d . . . . .
C14 C 0.7915(5) 0.7461(3) 0.5052(3) 0.0311(8) Uani 1 1 d . . . . .
C15 C 0.7996(5) 0.7334(3) 0.4073(3) 0.0309(8) Uani 1 1 d . . . . .
C16 C 0.8134(5) 0.8378(4) 0.3189(3) 0.0415(9) Uani 1 1 d . . . . .
H16 H 0.821059 0.830020 0.253660 0.050 Uiso 1 1 calc R . . . .
C17 C 0.8153(6) 0.9521(4) 0.3303(3) 0.0464(10) Uani 1 1 d . . . . .
H17 H 0.820545 1.022705 0.271811 0.056 Uiso 1 1 calc R . . . .
C18 C 0.8096(6) 0.9658(4) 0.4271(3) 0.0481(10) Uani 1 1 d . . . . .
H18 H 0.812210 1.044823 0.432091 0.058 Uiso 1 1 calc R . . . .
C19 C 0.8001(6) 0.8627(4) 0.5159(3) 0.0431(9) Uani 1 1 d . . . . .
H19 H 0.799351 0.870753 0.580527 0.052 Uiso 1 1 calc R . . . .
C20 C 0.7180(5) 0.3343(4) 0.5314(3) 0.0390(9) Uani 1 1 d . . . . .
H20 H 0.729583 0.354609 0.459944 0.047 Uiso 1 1 calc R . . . .
C21 C 0.6811(6) 0.2165(4) 0.5937(3) 0.0428(9) Uani 1 1 d . . . . .
H21 H 0.667818 0.155654 0.564957 0.051 Uiso 1 1 calc R . . . .
C22 C 0.6634(5) 0.1877(3) 0.7003(3) 0.0378(9) Uani 1 1 d . . . . .
H22 H 0.636976 0.107970 0.743574 0.045 Uiso 1 1 calc R . . . .
C23 C 0.6392(5) 0.1570(3) 0.9338(3) 0.0339(8) Uani 1 1 d . . . . .
H23 H 0.617148 0.084494 0.922355 0.041 Uiso 1 1 calc R . . . .
C24 C 0.6379(5) 0.1602(3) 1.0332(3) 0.0357(8) Uani 1 1 d . . . . .
H24 H 0.613258 0.089018 1.089346 0.043 Uiso 1 1 calc R . . . .
C25 C 0.6731(5) 0.2684(3) 1.0495(3) 0.0344(8) Uani 1 1 d . . . . .
H25 H 0.675617 0.270575 1.115829 0.041 Uiso 1 1 calc R . . . .


_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 2.129(3) . ?
Co1 O3 2.109(2) . ?
Co1 N1 2.216(3) . ?
Co1 N3 2.147(3) . ?
Co1 N4 2.108(3) . ?
Co1 N5 2.114(3) . ?
O1 C1 1.194(4) . ?
O3 H3A 0.9600 . ?
O3 H3B 0.9600 . ?
O2 C1 1.231(4) . ?
N1 C2 1.330(4) . ?
N1 C4 1.382(4) . ?
N2 H2 0.8600 . ?
N2 C2 1.359(4) . ?
N2 C3 1.379(4) . ?
N3 C9 1.347(4) . ?
N3 C10 1.333(4) . ?
N4 C11 1.341(4) . ?
N4 C12 1.340(4) . ?
N5 C13 1.348(4) . ?
N5 C14 1.373(4) . ?
N6 C13 1.340(4) . ?
N6 C15 1.384(4) . ?
C1 H1 0.9300 . ?
C2 C9 1.462(5) . ?
C3 C4 1.395(4) . ?
C3 C8 1.391(5) . ?
C4 C5 1.403(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.372(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.412(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.374(5) . ?
C8 H8 0.9300 . ?
C9 C25 1.371(5) . ?
C10 C11 1.486(5) . ?
C10 C23 1.389(5) . ?
C11 C22 1.378(5) . ?
C12 C13 1.481(5) . ?
C12 C20 1.378(5) . ?
C14 C15 1.403(5) . ?
C14 C19 1.398(5) . ?
C15 C16 1.392(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.368(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.397(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.385(5) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.364(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.389(5) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C23 C24 1.388(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.387(5) . ?
C25 H25 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 N1 86.33(10) . . ?
O1 Co1 N3 88.32(10) . . ?
O3 Co1 O1 171.32(10) . . ?
O3 Co1 N1 85.88(9) . . ?
O3 Co1 N3 93.38(10) . . ?
O3 Co1 N4 91.97(10) . . ?
O3 Co1 N5 91.36(10) . . ?
N3 Co1 N1 75.03(10) . . ?
N4 Co1 O1 96.67(10) . . ?
N4 Co1 N1 147.67(10) . . ?
N4 Co1 N3 72.90(10) . . ?
N4 Co1 N5 76.77(11) . . ?
N5 Co1 O1 91.50(10) . . ?
N5 Co1 N1 135.47(11) . . ?
N5 Co1 N3 149.44(11) . . ?
C1 O1 Co1 126.6(2) . . ?
Co1 O3 H3A 109.2 . . ?
Co1 O3 H3B 109.3 . . ?
H3A O3 H3B 109.5 . . ?
C2 N1 Co1 112.0(2) . . ?
C2 N1 C4 104.9(3) . . ?
C4 N1 Co1 142.9(2) . . ?
C2 N2 H2 126.6 . . ?
C2 N2 C3 106.7(3) . . ?
C3 N2 H2 126.6 . . ?
C9 N3 Co1 119.7(2) . . ?
C10 N3 Co1 120.0(2) . . ?
C10 N3 C9 120.3(3) . . ?
C11 N4 Co1 121.2(2) . . ?
C11 N4 C12 120.4(3) . . ?
C12 N4 Co1 118.4(2) . . ?
C13 N5 Co1 114.3(2) . . ?
C13 N5 C14 102.9(3) . . ?
C14 N5 Co1 142.8(2) . . ?
C13 N6 C15 102.0(3) . . ?
O1 C1 O2 128.1(4) . . ?
O1 C1 H1 116.0 . . ?
O2 C1 H1 116.0 . . ?
N1 C2 N2 112.8(3) . . ?
N1 C2 C9 122.0(3) . . ?
N2 C2 C9 125.2(3) . . ?
N2 C3 C4 105.8(3) . . ?
N2 C3 C8 131.2(3) . . ?
C8 C3 C4 123.1(3) . . ?
N1 C4 C3 109.8(3) . . ?
N1 C4 C5 130.2(3) . . ?
C3 C4 C5 119.9(3) . . ?
C4 C5 H5 121.3 . . ?
C6 C5 C4 117.5(3) . . ?
C6 C5 H5 121.3 . . ?
C5 C6 H6 119.2 . . ?
C5 C6 C7 121.6(3) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 H7 119.2 . . ?
C8 C7 C6 121.7(3) . . ?
C8 C7 H7 119.2 . . ?
C3 C8 H8 121.9 . . ?
C7 C8 C3 116.3(3) . . ?
C7 C8 H8 121.9 . . ?
N3 C9 C2 111.2(3) . . ?
N3 C9 C25 122.1(3) . . ?
C25 C9 C2 126.7(3) . . ?
N3 C10 C11 113.0(3) . . ?
N3 C10 C23 121.3(3) . . ?
C23 C10 C11 125.7(3) . . ?
N4 C11 C10 112.9(3) . . ?
N4 C11 C22 120.8(3) . . ?
C22 C11 C10 126.4(3) . . ?
N4 C12 C13 112.0(3) . . ?
N4 C12 C20 121.1(3) . . ?
C20 C12 C13 126.9(3) . . ?
N5 C13 C12 118.3(3) . . ?
N6 C13 N5 117.3(3) . . ?
N6 C13 C12 124.4(3) . . ?
N5 C14 C15 108.4(3) . . ?
N5 C14 C19 130.6(3) . . ?
C19 C14 C15 121.0(3) . . ?
N6 C15 C14 109.3(3) . . ?
N6 C15 C16 130.3(3) . . ?
C16 C15 C14 120.3(3) . . ?
C15 C16 H16 120.8 . . ?
C17 C16 C15 118.3(4) . . ?
C17 C16 H16 120.8 . . ?
C16 C17 H17 119.0 . . ?
C16 C17 C18 122.0(4) . . ?
C18 C17 H17 119.0 . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.5(4) . . ?
C19 C18 H18 119.7 . . ?
C14 C19 H19 121.1 . . ?
C18 C19 C14 117.9(4) . . ?
C18 C19 H19 121.1 . . ?
C12 C20 H20 120.5 . . ?
C21 C20 C12 119.1(3) . . ?
C21 C20 H20 120.5 . . ?
C20 C21 H21 120.1 . . ?
C20 C21 C22 119.8(3) . . ?
C22 C21 H21 120.1 . . ?
C11 C22 C21 118.8(3) . . ?
C11 C22 H22 120.6 . . ?
C21 C22 H22 120.6 . . ?
C10 C23 H23 121.0 . . ?
C10 C23 C24 118.0(3) . . ?
C24 C23 H23 121.0 . . ?
C23 C24 H24 119.7 . . ?
C25 C24 C23 120.7(3) . . ?
C25 C24 H24 119.7 . . ?
C9 C25 C24 117.7(3) . . ?
C9 C25 H25 121.1 . . ?
C24 C25 H25 121.1 . . ?

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
Co1 O1 C1 O2 167.1(3) . . . . ?
Co1 N1 C2 N2 -175.8(2) . . . . ?
Co1 N1 C2 C9 4.1(4) . . . . ?
Co1 N1 C4 C3 174.1(3) . . . . ?
Co1 N1 C4 C5 -5.8(6) . . . . ?
Co1 N3 C9 C2 -0.7(4) . . . . ?
Co1 N3 C9 C25 -179.4(2) . . . . ?
Co1 N3 C10 C11 0.9(4) . . . . ?
Co1 N3 C10 C23 -179.7(2) . . . . ?
Co1 N4 C11 C10 -0.9(4) . . . . ?
Co1 N4 C11 C22 179.7(2) . . . . ?
Co1 N4 C12 C13 -2.3(4) . . . . ?
Co1 N4 C12 C20 179.8(3) . . . . ?
Co1 N5 C13 N6 -177.2(2) . . . . ?
Co1 N5 C13 C12 5.2(4) . . . . ?
Co1 N5 C14 C15 177.0(3) . . . . ?
Co1 N5 C14 C19 -4.0(7) . . . . ?
N1 C2 C9 N3 -2.4(4) . . . . ?
N1 C2 C9 C25 176.1(3) . . . . ?
N1 C4 C5 C6 179.2(3) . . . . ?
N2 C2 C9 N3 177.5(3) . . . . ?
N2 C2 C9 C25 -4.0(5) . . . . ?
N2 C3 C4 N1 0.0(4) . . . . ?
N2 C3 C4 C5 179.9(3) . . . . ?
N2 C3 C8 C7 -179.2(3) . . . . ?
N3 C9 C25 C24 -1.1(5) . . . . ?
N3 C10 C11 N4 0.0(4) . . . . ?
N3 C10 C11 C22 179.3(3) . . . . ?
N3 C10 C23 C24 -0.8(5) . . . . ?
N4 C11 C22 C21 0.2(5) . . . . ?
N4 C12 C13 N5 -2.0(4) . . . . ?
N4 C12 C13 N6 -179.4(3) . . . . ?
N4 C12 C20 C21 0.6(5) . . . . ?
N5 C14 C15 N6 -0.4(4) . . . . ?
N5 C14 C15 C16 178.1(3) . . . . ?
N5 C14 C19 C18 -176.5(4) . . . . ?
N6 C15 C16 C17 177.0(3) . . . . ?
C2 N1 C4 C3 -0.4(4) . . . . ?
C2 N1 C4 C5 179.8(3) . . . . ?
C2 N2 C3 C4 0.4(3) . . . . ?
C2 N2 C3 C8 -179.7(3) . . . . ?
C2 C9 C25 C24 -179.5(3) . . . . ?
C3 N2 C2 N1 -0.6(4) . . . . ?
C3 N2 C2 C9 179.5(3) . . . . ?
C3 C4 C5 C6 -0.6(5) . . . . ?
C4 N1 C2 N2 0.6(4) . . . . ?
C4 N1 C2 C9 -179.5(3) . . . . ?
C4 C3 C8 C7 0.7(5) . . . . ?
C4 C5 C6 C7 0.7(5) . . . . ?
C5 C6 C7 C8 0.0(6) . . . . ?
C6 C7 C8 C3 -0.6(5) . . . . ?
C8 C3 C4 N1 -179.9(3) . . . . ?
C8 C3 C4 C5 0.0(5) . . . . ?
C9 N3 C10 C11 -178.0(3) . . . . ?
C9 N3 C10 C23 1.4(5) . . . . ?
C10 N3 C9 C2 178.3(3) . . . . ?
C10 N3 C9 C25 -0.4(5) . . . . ?
C10 C11 C22 C21 -179.1(3) . . . . ?
C10 C23 C24 C25 -0.7(5) . . . . ?
C11 N4 C12 C13 176.7(3) . . . . ?
C11 N4 C12 C20 -1.2(5) . . . . ?
C11 C10 C23 C24 178.5(3) . . . . ?
C12 N4 C11 C10 -179.9(3) . . . . ?
C12 N4 C11 C22 0.7(5) . . . . ?
C12 C20 C21 C22 0.3(6) . . . . ?
C13 N5 C14 C15 -0.4(4) . . . . ?
C13 N5 C14 C19 178.6(4) . . . . ?
C13 N6 C15 C14 0.9(4) . . . . ?
C13 N6 C15 C16 -177.3(4) . . . . ?
C13 C12 C20 C21 -176.8(3) . . . . ?
C14 N5 C13 N6 1.1(4) . . . . ?
C14 N5 C13 C12 -176.5(3) . . . . ?
C14 C15 C16 C17 -1.2(5) . . . . ?
C15 N6 C13 N5 -1.3(4) . . . . ?
C15 N6 C13 C12 176.1(3) . . . . ?
C15 C14 C19 C18 2.4(6) . . . . ?
C15 C16 C17 C18 1.9(6) . . . . ?
C16 C17 C18 C19 -0.6(6) . . . . ?
C17 C18 C19 C14 -1.6(6) . . . . ?
C19 C14 C15 N6 -179.5(3) . . . . ?
C19 C14 C15 C16 -1.0(5) . . . . ?
C20 C12 C13 N5 175.7(3) . . . . ?
C20 C12 C13 N6 -1.8(6) . . . . ?
C20 C21 C22 C11 -0.7(6) . . . . ?
C23 C10 C11 N4 -179.4(3) . . . . ?
C23 C10 C11 C22 0.0(6) . . . . ?
C23 C24 C25 C9 1.6(5) . . . . ?

