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

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

data_2
_database_code_depnum_ccdc_archive 'CCDC 1560005'
_audit_update_record             
;
2017-07-03 deposited with the CCDC.
2017-09-13 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            'C23 H41 Co2 N16 O2'
_chemical_formula_weight         691.58

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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 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'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   8.6745(14)
_cell_length_b                   13.701(2)
_cell_length_c                   26.368(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3133.9(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5452
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      23.24

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            Brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_F_000             1444
_exptl_transmission_factor_min   0.843
_exptl_transmission_factor_max   0.878
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.109
_shelx_estimated_absorpt_T_min   0.843
_shelx_estimated_absorpt_T_max   0.878
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21853
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.545
_diffrn_reflns_theta_max         25.159
_diffrn_reflns_theta_full        25.159
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5592
_reflns_number_gt                4785
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.995

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-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)+(0.0900P)²+0.3000P] 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 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.51(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5592
_refine_ls_number_parameters     384
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1387
_refine_ls_wR_factor_gt          0.1308
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.028
_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 0.2809(8) -0.0034(5) 0.2505(2) 0.0371(14) Uani 1 1 d . . . . .
C2 C 0.3890(8) -0.0736(5) 0.2674(2) 0.0404(15) Uani 1 1 d . . . . .
C3 C 0.4102(9) -0.0886(6) 0.3191(3) 0.0488(18) Uani 1 1 d . . . . .
H3 H 0.4796 -0.1363 0.3295 0.059 Uiso 1 1 calc R U . . .
C4 C 0.3324(10) -0.0357(6) 0.3559(2) 0.0537(17) Uani 1 1 d . . . . .
C5 C 0.2311(8) 0.0343(5) 0.3390(2) 0.0456(16) Uani 1 1 d . . . . .
H5 H 0.1791 0.0719 0.3629 0.055 Uiso 1 1 calc R U . . .
C6 C 0.2030(7) 0.0513(5) 0.2873(2) 0.0392(15) Uani 1 1 d . . . . .
C7 C 0.3594(12) -0.0583(8) 0.4120(3) 0.076(3) Uani 1 1 d D . . . .
H7A H 0.2668 -0.0433 0.4311 0.091 Uiso 1 1 calc R U . . .
H7B H 0.3812 -0.1273 0.4161 0.091 Uiso 1 1 calc R U . . .
C8 C 0.4899(14) -0.0003(9) 0.4320(4) 0.106(4) Uani 1 1 d D . . . .
H8A H 0.5842 -0.0225 0.4168 0.160 Uiso 1 1 calc R U . . .
H8B H 0.4958 -0.0083 0.4681 0.160 Uiso 1 1 calc R U . . .
H8C H 0.4744 0.0673 0.4241 0.160 Uiso 1 1 calc R U . . .
C9 C 0.0951(8) 0.1294(5) 0.2747(3) 0.0446(16) Uani 1 1 d . . . . .
H9 H 0.0443 0.1597 0.3015 0.053 Uiso 1 1 calc R U . . .
C10 C -0.0472(9) 0.2377(5) 0.2226(3) 0.0538(19) Uani 1 1 d . . . . .
H10A H -0.0592 0.2756 0.2534 0.065 Uiso 1 1 calc R U . . .
H10B H -0.1468 0.2111 0.2131 0.065 Uiso 1 1 calc R U . . .
C11 C 0.0158(10) 0.3001(5) 0.1808(3) 0.0544(19) Uani 1 1 d . . . . .
H11A H 0.1071 0.3340 0.1926 0.065 Uiso 1 1 calc R U . . .
H11B H -0.0602 0.3487 0.1713 0.065 Uiso 1 1 calc R U . . .
C12 C 0.1578(10) 0.2947(5) 0.1030(3) 0.0569(18) Uani 1 1 d . . . . .
H12A H 0.1905 0.2523 0.0755 0.068 Uiso 1 1 calc R U . . .
H12B H 0.2490 0.3108 0.1225 0.068 Uiso 1 1 calc R U . . .
C13 C 0.0964(12) 0.3900(7) 0.0792(4) 0.078(3) Uani 1 1 d . . . . .
H13A H 0.0136 0.3751 0.0563 0.118 Uiso 1 1 calc R U . . .
H13B H 0.1780 0.4218 0.0609 0.118 Uiso 1 1 calc R U . . .
H13C H 0.0595 0.4324 0.1055 0.118 Uiso 1 1 calc R U . . .
C14 C -0.0939(10) 0.2150(7) 0.1086(4) 0.065(2) Uani 1 1 d . . . . .
H14A H -0.1573 0.1761 0.1312 0.078 Uiso 1 1 calc R U . . .
H14B H -0.1487 0.2754 0.1020 0.078 Uiso 1 1 calc R U . . .
C15 C -0.0757(13) 0.1610(8) 0.0595(4) 0.084(3) Uani 1 1 d . . . . .
H15A H -0.0167 0.1999 0.0363 0.126 Uiso 1 1 calc R U . . .
H15B H -0.1755 0.1481 0.0453 0.126 Uiso 1 1 calc R U . . .
H15C H -0.0233 0.1004 0.0655 0.126 Uiso 1 1 calc R U . . .
C16 C 0.4904(9) -0.1292(6) 0.2342(3) 0.0494(17) Uani 1 1 d . . . . .
H16 H 0.5634 -0.1686 0.2500 0.059 Uiso 1 1 calc R U . . .
C17 C 0.6115(10) -0.1876(7) 0.1606(3) 0.066(2) Uani 1 1 d . . . . .
H17A H 0.6387 -0.2433 0.1815 0.080 Uiso 1 1 calc R U . . .
H17B H 0.7030 -0.1479 0.1560 0.080 Uiso 1 1 calc R U . . .
C18 C 0.5535(10) -0.2220(6) 0.1100(3) 0.057(2) Uani 1 1 d . . . . .
H18A H 0.6380 -0.2500 0.0908 0.068 Uiso 1 1 calc R U . . .
H18B H 0.4764 -0.2724 0.1150 0.068 Uiso 1 1 calc R U . . .
C19 C 0.4024(15) -0.1843(7) 0.0366(4) 0.092(4) Uani 1 1 d . . . . .
H19A H 0.4779 -0.2137 0.0142 0.111 Uiso 1 1 calc R U . . .
H19B H 0.3357 -0.2360 0.0489 0.111 Uiso 1 1 calc R U . . .
C20 C 0.309(2) -0.1149(9) 0.0073(4) 0.140(6) Uani 1 1 d . . . . .
H20A H 0.2086 -0.1097 0.0222 0.210 Uiso 1 1 calc R U . . .
H20B H 0.2999 -0.1375 -0.0270 0.210 Uiso 1 1 calc R U . . .
H20C H 0.3582 -0.0521 0.0075 0.210 Uiso 1 1 calc R U . . .
C21 C 0.5978(13) -0.0661(7) 0.0671(4) 0.083(3) Uani 1 1 d . . . . .
H21A H 0.6419 -0.0392 0.0978 0.099 Uiso 1 1 calc R U . . .
H21B H 0.5444 -0.0135 0.0498 0.099 Uiso 1 1 calc R U . . .
C22 C 0.7281(17) -0.1009(9) 0.0334(6) 0.138(6) Uani 1 1 d . . . . .
H22A H 0.7996 -0.1385 0.0532 0.207 Uiso 1 1 calc R U . . .
H22B H 0.7802 -0.0456 0.0191 0.207 Uiso 1 1 calc R U . . .
H22C H 0.6872 -0.1408 0.0067 0.207 Uiso 1 1 calc R U . . .
C23 C 0.7612(16) 0.0140(11) 0.3122(5) 0.117(4) Uani 1 1 d . . . . .
H23A H 0.8332 0.0132 0.3398 0.175 Uiso 1 1 calc R U . . .
H23B H 0.8158 0.0075 0.2807 0.175 Uiso 1 1 calc R U . . .
H23C H 0.6902 -0.0393 0.3158 0.175 Uiso 1 1 calc R U . . .
Co1 Co 0.15920(10) 0.11831(6) 0.16941(3) 0.0366(2) Uani 1 1 d . . . . .
Co2 Co 0.32712(11) -0.07643(6) 0.13861(3) 0.0418(3) Uani 1 1 d . . . . .
N1 N 0.0646(6) 0.1594(4) 0.2301(2) 0.0404(13) Uani 1 1 d . . . . .
N2 N 0.0559(7) 0.2389(4) 0.1354(2) 0.0479(14) Uani 1 1 d . . . . .
N3 N 0.4898(7) -0.1297(5) 0.1859(2) 0.0477(14) Uani 1 1 d . . . . .
N4 N 0.4852(9) -0.1400(4) 0.0811(2) 0.0540(16) Uani 1 1 d . . . . .
N5 N 0.3378(7) 0.1988(4) 0.1855(2) 0.0461(13) Uani 1 1 d . . . . .
N6 N 0.4625(7) 0.1626(5) 0.1825(3) 0.0572(17) Uani 1 1 d . . . . .
N7 N 0.5822(9) 0.1272(8) 0.1798(5) 0.116(4) Uani 1 1 d . . . . .
N8 N -0.0198(7) 0.0355(5) 0.1553(2) 0.0513(15) Uani 1 1 d . . . . .
N9 N -0.0679(7) -0.0138(5) 0.1887(3) 0.0527(16) Uani 1 1 d . . . . .
N10 N -0.1178(10) -0.0623(6) 0.2201(3) 0.081(2) Uani 1 1 d . . . . .
N11 N 0.2668(7) 0.0581(4) 0.1096(2) 0.0472(14) Uani 1 1 d . . . . .
N12 N 0.3281(17) 0.1009(7) 0.0753(4) 0.132(4) Uani 1 1 d . . . . .
N13 N 0.3760(17) 0.1367(7) 0.0408(3) 0.132(4) Uani 1 1 d . . . . .
N14 N 0.1626(12) -0.1769(6) 0.1383(4) 0.089(2) Uani 1 1 d . . . . .
N15 N 0.0780(13) -0.2201(9) 0.1190(4) 0.111(3) Uani 1 1 d . . . . .
N16 N -0.0090(13) -0.2716(8) 0.1010(3) 0.111(3) Uani 1 1 d . . . . .
O1 O 0.2539(5) 0.0088(3) 0.20161(16) 0.0402(10) Uani 1 1 d . . . . .
O2 O 0.683(2) 0.0989(11) 0.3124(10) 0.261(11) Uani 1 1 d . . . . .
H2 H 0.7435 0.1444 0.3095 0.392 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 1.322(7) . ?
C1 C6 1.400(9) . ?
C1 C2 1.415(9) . ?
C2 C3 1.392(9) . ?
C2 C16 1.456(10) . ?
C3 C4 1.385(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(11) . ?
C4 C7 1.530(10) . ?
C5 C6 1.404(9) . ?
C5 H5 0.9300 . ?
C6 C9 1.460(10) . ?
C7 C8 1.480(10) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 N1 1.274(9) . ?
C9 H9 0.9300 . ?
C10 N1 1.460(9) . ?
C10 C11 1.498(11) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N2 1.501(9) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N2 1.448(10) . ?
C12 C13 1.544(11) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.500(13) . ?
C14 N2 1.515(10) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 N3 1.273(8) . ?
C16 H16 0.9300 . ?
C17 N3 1.480(10) . ?
C17 C18 1.503(11) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 N4 1.481(10) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.468(15) . ?
C19 N4 1.503(11) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 N4 1.455(12) . ?
C21 C22 1.514(13) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 O2 1.347(19) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
Co1 N1 1.885(6) . ?
Co1 O1 1.910(4) . ?
Co1 N5 1.948(6) . ?
Co1 N8 1.959(6) . ?
Co1 N11 2.009(6) . ?
Co1 N2 2.082(6) . ?
Co2 N14 1.983(9) . ?
Co2 N3 2.020(6) . ?
Co2 N11 2.063(6) . ?
Co2 O1 2.127(4) . ?
Co2 N4 2.222(6) . ?
N5 N6 1.193(9) . ?
N6 N7 1.148(10) . ?
N8 N9 1.186(9) . ?
N9 N10 1.145(10) . ?
N11 N12 1.202(10) . ?
N12 N13 1.114(11) . ?
N14 N15 1.071(11) . ?
N15 N16 1.137(13) . ?
O2 H2 0.8200 . ?

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 C6 121.6(6) . . ?
O1 C1 C2 120.6(6) . . ?
C6 C1 C2 117.8(5) . . ?
C3 C2 C1 119.7(6) . . ?
C3 C2 C16 115.6(6) . . ?
C1 C2 C16 124.6(6) . . ?
C4 C3 C2 123.0(7) . . ?
C4 C3 H3 118.5 . . ?
C2 C3 H3 118.5 . . ?
C5 C4 C3 116.7(6) . . ?
C5 C4 C7 123.4(8) . . ?
C3 C4 C7 119.8(8) . . ?
C4 C5 C6 122.7(6) . . ?
C4 C5 H5 118.6 . . ?
C6 C5 H5 118.6 . . ?
C1 C6 C5 120.0(6) . . ?
C1 C6 C9 123.0(6) . . ?
C5 C6 C9 117.0(6) . . ?
C8 C7 C4 110.7(8) . . ?
C8 C7 H7A 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C6 125.4(6) . . ?
N1 C9 H9 117.3 . . ?
C6 C9 H9 117.3 . . ?
N1 C10 C11 106.1(6) . . ?
N1 C10 H10A 110.5 . . ?
C11 C10 H10A 110.5 . . ?
N1 C10 H10B 110.5 . . ?
C11 C10 H10B 110.5 . . ?
H10A C10 H10B 108.7 . . ?
C10 C11 N2 110.6(6) . . ?
C10 C11 H11A 109.5 . . ?
N2 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
N2 C12 C13 118.4(7) . . ?
N2 C12 H12A 107.7 . . ?
C13 C12 H12A 107.7 . . ?
N2 C12 H12B 107.7 . . ?
C13 C12 H12B 107.7 . . ?
H12A C12 H12B 107.1 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 N2 114.8(7) . . ?
C15 C14 H14A 108.6 . . ?
N2 C14 H14A 108.6 . . ?
C15 C14 H14B 108.6 . . ?
N2 C14 H14B 108.6 . . ?
H14A C14 H14B 107.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 C2 126.9(7) . . ?
N3 C16 H16 116.5 . . ?
C2 C16 H16 116.5 . . ?
N3 C17 C18 109.2(7) . . ?
N3 C17 H17A 109.8 . . ?
C18 C17 H17A 109.8 . . ?
N3 C17 H17B 109.8 . . ?
C18 C17 H17B 109.8 . . ?
H17A C17 H17B 108.3 . . ?
N4 C18 C17 110.7(6) . . ?
N4 C18 H18A 109.5 . . ?
C17 C18 H18A 109.5 . . ?
N4 C18 H18B 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
C20 C19 N4 114.4(8) . . ?
C20 C19 H19A 108.7 . . ?
N4 C19 H19A 108.7 . . ?
C20 C19 H19B 108.7 . . ?
N4 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N4 C21 C22 115.5(8) . . ?
N4 C21 H21A 108.4 . . ?
C22 C21 H21A 108.4 . . ?
N4 C21 H21B 108.4 . . ?
C22 C21 H21B 108.4 . . ?
H21A C21 H21B 107.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N1 Co1 O1 92.5(2) . . ?
N1 Co1 N5 89.5(2) . . ?
O1 Co1 N5 90.3(2) . . ?
N1 Co1 N8 89.4(3) . . ?
O1 Co1 N8 88.3(2) . . ?
N5 Co1 N8 178.2(3) . . ?
N1 Co1 N11 172.4(2) . . ?
O1 Co1 N11 80.0(2) . . ?
N5 Co1 N11 92.0(3) . . ?
N8 Co1 N11 88.9(3) . . ?
N1 Co1 N2 86.6(2) . . ?
O1 Co1 N2 179.1(2) . . ?
N5 Co1 N2 89.2(2) . . ?
N8 Co1 N2 92.1(2) . . ?
N11 Co1 N2 100.9(2) . . ?
N14 Co2 N3 104.7(3) . . ?
N14 Co2 N11 115.9(3) . . ?
N3 Co2 N11 136.8(3) . . ?
N14 Co2 O1 99.7(3) . . ?
N3 Co2 O1 85.7(2) . . ?
N11 Co2 O1 73.9(2) . . ?
N14 Co2 N4 99.8(3) . . ?
N3 Co2 N4 81.3(2) . . ?
N11 Co2 N4 104.7(2) . . ?
O1 Co2 N4 158.8(2) . . ?
C9 N1 C10 120.0(6) . . ?
C9 N1 Co1 126.7(5) . . ?
C10 N1 Co1 113.2(5) . . ?
C12 N2 C11 108.5(6) . . ?
C12 N2 C14 111.2(6) . . ?
C11 N2 C14 107.1(6) . . ?
C12 N2 Co1 114.2(4) . . ?
C11 N2 Co1 101.5(4) . . ?
C14 N2 Co1 113.4(5) . . ?
C16 N3 C17 116.8(6) . . ?
C16 N3 Co2 128.2(5) . . ?
C17 N3 Co2 114.5(4) . . ?
C21 N4 C18 113.0(7) . . ?
C21 N4 C19 113.8(8) . . ?
C18 N4 C19 106.6(6) . . ?
C21 N4 Co2 108.4(4) . . ?
C18 N4 Co2 101.2(4) . . ?
C19 N4 Co2 113.3(6) . . ?
N6 N5 Co1 118.1(5) . . ?
N7 N6 N5 179.4(11) . . ?
N9 N8 Co1 117.9(5) . . ?
N10 N9 N8 178.0(8) . . ?
N12 N11 Co1 126.6(6) . . ?
N12 N11 Co2 127.1(6) . . ?
Co1 N11 Co2 101.2(3) . . ?
N13 N12 N11 174.0(17) . . ?
N15 N14 Co2 151.5(9) . . ?
N14 N15 N16 174.8(14) . . ?
C1 O1 Co1 127.5(4) . . ?
C1 O1 Co2 129.8(4) . . ?
Co1 O1 Co2 102.27(19) . . ?
C23 O2 H2 109.5 . . ?

_refine_diff_density_max         0.951
_refine_diff_density_min         -0.864
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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 1560004'
_audit_update_record             
;
2017-07-03 deposited with the CCDC.
2017-09-13 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            'C22 H39 Co2 N16 O2'
_chemical_formula_weight         677.55

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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 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'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   8.424(6)
_cell_length_b                   13.764(9)
_cell_length_c                   25.759(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2987(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1419
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      17.74

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            Brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_F_000             1412
_exptl_transmission_factor_min   0.836
_exptl_transmission_factor_max   0.873
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.162
_shelx_estimated_absorpt_T_min   0.836
_shelx_estimated_absorpt_T_max   0.873
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14078
_diffrn_reflns_av_unetI/netI     0.1580
_diffrn_reflns_av_R_equivalents  0.1148
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.581
_diffrn_reflns_theta_max         25.597
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5331
_reflns_number_gt                2668
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.997

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-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)+(0.0900P)²+0.6696P] 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 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.43(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5331
_refine_ls_number_parameters     375
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1673
_refine_ls_R_factor_gt           0.0797
_refine_ls_wR_factor_ref         0.2173
_refine_ls_wR_factor_gt          0.1745
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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 0.7139(17) -0.0083(10) 0.2497(6) 0.054(4) Uani 1 1 d . . . . .
C2 C 0.6058(16) -0.0786(10) 0.2342(6) 0.054(4) Uani 1 1 d . . . . .
C3 C 0.5797(17) -0.0942(10) 0.1818(6) 0.058(4) Uani 1 1 d . . . . .
H3 H 0.5093 -0.1429 0.1721 0.070 Uiso 1 1 calc R U . . .
C4 C 0.653(2) -0.0413(11) 0.1435(6) 0.065(4) Uani 1 1 d . . . . .
C5 C 0.7616(17) 0.0308(11) 0.1595(6) 0.062(4) Uani 1 1 d . . . . .
H5 H 0.8139 0.0683 0.1348 0.074 Uiso 1 1 calc R U . . .
C6 C 0.7903(15) 0.0455(10) 0.2110(6) 0.051(4) Uani 1 1 d . . . . .
C7 C 0.620(2) -0.0560(15) 0.0875(7) 0.096(6) Uani 1 1 d . . . . .
H7A H 0.5720 -0.1187 0.0824 0.143 Uiso 1 1 calc R U . . .
H7B H 0.7174 -0.0526 0.0684 0.143 Uiso 1 1 calc R U . . .
H7C H 0.5487 -0.0064 0.0755 0.143 Uiso 1 1 calc R U . . .
C8 C 0.9027(16) 0.1252(12) 0.2247(7) 0.064(4) Uani 1 1 d . . . . .
H8 H 0.9560 0.1551 0.1975 0.077 Uiso 1 1 calc R U . . .
C9 C 1.0442(18) 0.2329(11) 0.2774(7) 0.069(5) Uani 1 1 d . . . . .
H9A H 1.1451 0.2066 0.2888 0.083 Uiso 1 1 calc R U . . .
H9B H 1.0613 0.2691 0.2455 0.083 Uiso 1 1 calc R U . . .
C10 C 0.978(2) 0.2956(11) 0.3169(7) 0.070(5) Uani 1 1 d . . . . .
H10A H 0.8839 0.3275 0.3038 0.085 Uiso 1 1 calc R U . . .
H10B H 1.0551 0.3453 0.3262 0.085 Uiso 1 1 calc R U . . .
C11 C 1.0900(19) 0.2136(13) 0.3943(8) 0.085(6) Uani 1 1 d . . . . .
H11A H 1.1587 0.1748 0.3723 0.102 Uiso 1 1 calc R U . . .
H11B H 1.1439 0.2747 0.4008 0.102 Uiso 1 1 calc R U . . .
C12 C 1.070(3) 0.1618(14) 0.4451(8) 0.102(7) Uani 1 1 d . . . . .
H12A H 1.0210 0.2046 0.4698 0.153 Uiso 1 1 calc R U . . .
H12B H 1.1722 0.1420 0.4579 0.153 Uiso 1 1 calc R U . . .
H12C H 1.0044 0.1055 0.4402 0.153 Uiso 1 1 calc R U . . .
C13 C 0.831(2) 0.2915(10) 0.3968(6) 0.075(5) Uani 1 1 d . . . . .
H13A H 0.8028 0.2519 0.4265 0.090 Uiso 1 1 calc R U . . .
H13B H 0.7345 0.3030 0.3772 0.090 Uiso 1 1 calc R U . . .
C14 C 0.891(2) 0.3901(12) 0.4172(8) 0.098(6) Uani 1 1 d . . . . .
H14A H 0.9718 0.3796 0.4428 0.147 Uiso 1 1 calc R U . . .
H14B H 0.8040 0.4250 0.4325 0.147 Uiso 1 1 calc R U . . .
H14C H 0.9337 0.4272 0.3889 0.147 Uiso 1 1 calc R U . . .
C15 C 0.505(2) -0.1357(11) 0.2685(6) 0.065(4) Uani 1 1 d . . . . .
H15 H 0.4315 -0.1767 0.2529 0.078 Uiso 1 1 calc R U . . .
C16 C 0.384(2) -0.1944(12) 0.3428(6) 0.079(5) Uani 1 1 d . . . . .
H16A H 0.3620 -0.2518 0.3223 0.094 Uiso 1 1 calc R U . . .
H16B H 0.2872 -0.1572 0.3464 0.094 Uiso 1 1 calc R U . . .
C17 C 0.446(2) -0.2230(12) 0.3954(7) 0.083(6) Uani 1 1 d . . . . .
H17A H 0.3603 -0.2507 0.4157 0.100 Uiso 1 1 calc R U . . .
H17B H 0.5275 -0.2722 0.3914 0.100 Uiso 1 1 calc R U . . .
C18 C 0.596(3) -0.1750(15) 0.4687(8) 0.119(8) Uani 1 1 d . . . . .
H18A H 0.5199 -0.2053 0.4917 0.143 Uiso 1 1 calc R U . . .
H18B H 0.6702 -0.2250 0.4577 0.143 Uiso 1 1 calc R U . . .
C19 C 0.683(4) -0.1029(15) 0.4979(9) 0.143(10) Uani 1 1 d . . . . .
H19A H 0.7730 -0.0815 0.4780 0.215 Uiso 1 1 calc R U . . .
H19B H 0.7193 -0.1308 0.5299 0.215 Uiso 1 1 calc R U . . .
H19C H 0.6153 -0.0486 0.5051 0.215 Uiso 1 1 calc R U . . .
C20 C 0.386(3) -0.0678(13) 0.4342(8) 0.101(7) Uani 1 1 d . . . . .
H20A H 0.3419 -0.0465 0.4014 0.121 Uiso 1 1 calc R U . . .
H20B H 0.4346 -0.0116 0.4505 0.121 Uiso 1 1 calc R U . . .
C21 C 0.249(3) -0.1024(16) 0.4690(10) 0.143(10) Uani 1 1 d . . . . .
H21A H 0.1934 -0.1547 0.4522 0.215 Uiso 1 1 calc R U . . .
H21B H 0.1764 -0.0495 0.4748 0.215 Uiso 1 1 calc R U . . .
H21C H 0.2899 -0.1245 0.5017 0.215 Uiso 1 1 calc R U . . .
C22 C 0.244(3) 0.023(2) 0.1860(11) 0.167(12) Uani 1 1 d . . . . .
H22A H 0.2453 0.0136 0.2229 0.251 Uiso 1 1 calc R U . . .
H22B H 0.2944 -0.0308 0.1692 0.251 Uiso 1 1 calc R U . . .
H22C H 0.1362 0.0284 0.1743 0.251 Uiso 1 1 calc R U . . .
Co1 Co 0.8366(2) 0.11556(13) 0.33091(8) 0.0557(6) Uani 1 1 d . . . . .
Co2 Co 0.6695(3) -0.07688(13) 0.36413(8) 0.0642(7) Uani 1 1 d . . . . .
N1 N 0.9315(13) 0.1550(9) 0.2686(5) 0.053(3) Uani 1 1 d . . . . .
N2 N 0.9373(13) 0.2351(9) 0.3643(6) 0.064(3) Uani 1 1 d . . . . .
N3 N 0.5087(14) -0.1345(9) 0.3170(6) 0.066(3) Uani 1 1 d . . . . .
N4 N 0.5126(18) -0.1389(9) 0.4232(5) 0.070(4) Uani 1 1 d . . . . .
N5 N 0.6488(17) 0.1926(8) 0.3142(5) 0.062(3) Uani 1 1 d . . . . .
N6 N 0.5268(19) 0.1543(11) 0.3134(7) 0.102(4) Uani 1 1 d . . . . .
N7 N 0.4036(16) 0.1193(12) 0.3128(7) 0.102(4) Uani 1 1 d . . . . .
N8 N 1.0219(15) 0.0353(9) 0.3462(5) 0.067(4) Uani 1 1 d . . . . .
N9 N 1.0720(15) -0.0144(11) 0.3124(7) 0.072(4) Uani 1 1 d . . . . .
N10 N 1.1192(19) -0.0627(13) 0.2807(8) 0.108(6) Uani 1 1 d . . . . .
N11 N 0.7258(15) 0.0584(11) 0.3905(6) 0.068(4) Uani 1 1 d . . . . .
N12 N 0.656(3) 0.1011(13) 0.4233(8) 0.108(6) Uani 1 1 d . . . . .
N13 N 0.597(4) 0.1419(16) 0.4565(10) 0.199(15) Uani 1 1 d . . . . .
N14 N 0.850(2) -0.1709(11) 0.3678(7) 0.107(4) Uani 1 1 d . . . . .
N15 N 0.920(2) -0.2250(15) 0.3844(8) 0.107(4) Uani 1 1 d . . . . .
N16 N 1.002(3) -0.2827(19) 0.3983(9) 0.173(10) Uani 1 1 d . . . . .
O1 O 0.7434(11) 0.0038(6) 0.2993(4) 0.055(2) Uani 1 1 d . . . . .
O2 O 0.322(3) 0.1044(17) 0.174(2) 0.39(3) Uani 1 1 d . . . . .
H2 H 0.2583 0.1493 0.1715 0.590 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 1.313(16) . ?
C1 C2 1.386(19) . ?
C1 C6 1.399(19) . ?
C2 C3 1.384(19) . ?
C2 C15 1.45(2) . ?
C3 C4 1.37(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.41(2) . ?
C4 C7 1.48(2) . ?
C5 C6 1.364(19) . ?
C5 H5 0.9300 . ?
C6 C8 1.49(2) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 N1 1.226(18) . ?
C8 H8 0.9300 . ?
C9 C10 1.45(2) . ?
C9 N1 1.449(18) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N2 1.519(19) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.50(2) . ?
C11 N2 1.529(19) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 N2 1.450(19) . ?
C13 C14 1.54(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 N3 1.250(16) . ?
C15 H15 0.9300 . ?
C16 N3 1.490(19) . ?
C16 C17 1.50(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 N4 1.47(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.44(2) . ?
C18 N4 1.46(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 N4 1.47(2) . ?
C20 C21 1.54(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 O2 1.33(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
Co1 N1 1.874(12) . ?
Co1 O1 1.910(9) . ?
Co1 N8 1.952(12) . ?
Co1 N5 1.952(13) . ?
Co1 N11 1.962(15) . ?
Co1 N2 2.041(12) . ?
Co2 N3 1.984(13) . ?
Co2 N14 1.998(17) . ?
Co2 N11 2.039(15) . ?
Co2 O1 2.099(10) . ?
Co2 N4 2.188(14) . ?
N5 N6 1.155(18) . ?
N6 N7 1.145(19) . ?
N8 N9 1.185(18) . ?
N9 N10 1.127(19) . ?
N11 N12 1.19(2) . ?
N12 N13 1.14(2) . ?
N14 N15 1.05(2) . ?
N15 N16 1.11(2) . ?
O2 H2 0.8200 . ?

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 C2 119.5(14) . . ?
O1 C1 C6 122.6(13) . . ?
C2 C1 C6 117.8(14) . . ?
C3 C2 C1 119.5(14) . . ?
C3 C2 C15 114.6(13) . . ?
C1 C2 C15 125.8(14) . . ?
C4 C3 C2 123.3(14) . . ?
C4 C3 H3 118.4 . . ?
C2 C3 H3 118.4 . . ?
C3 C4 C5 117.0(14) . . ?
C3 C4 C7 123.0(15) . . ?
C5 C4 C7 120.0(15) . . ?
C6 C5 C4 120.2(14) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 122.2(14) . . ?
C5 C6 C8 116.9(13) . . ?
C1 C6 C8 120.8(14) . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C6 126.2(15) . . ?
N1 C8 H8 116.9 . . ?
C6 C8 H8 116.9 . . ?
C10 C9 N1 107.5(13) . . ?
C10 C9 H9A 110.2 . . ?
N1 C9 H9A 110.2 . . ?
C10 C9 H9B 110.2 . . ?
N1 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
C9 C10 N2 109.0(12) . . ?
C9 C10 H10A 109.9 . . ?
N2 C10 H10A 109.9 . . ?
C9 C10 H10B 109.9 . . ?
N2 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
C12 C11 N2 116.0(15) . . ?
C12 C11 H11A 108.3 . . ?
N2 C11 H11A 108.3 . . ?
C12 C11 H11B 108.3 . . ?
N2 C11 H11B 108.3 . . ?
H11A C11 H11B 107.4 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 C14 117.9(16) . . ?
N2 C13 H13A 107.8 . . ?
C14 C13 H13A 107.8 . . ?
N2 C13 H13B 107.8 . . ?
C14 C13 H13B 107.8 . . ?
H13A C13 H13B 107.2 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C15 C2 125.9(15) . . ?
N3 C15 H15 117.1 . . ?
C2 C15 H15 117.1 . . ?
N3 C16 C17 107.8(14) . . ?
N3 C16 H16A 110.1 . . ?
C17 C16 H16A 110.1 . . ?
N3 C16 H16B 110.1 . . ?
C17 C16 H16B 110.1 . . ?
H16A C16 H16B 108.5 . . ?
N4 C17 C16 111.3(13) . . ?
N4 C17 H17A 109.4 . . ?
C16 C17 H17A 109.4 . . ?
N4 C17 H17B 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C19 C18 N4 115.5(16) . . ?
C19 C18 H18A 108.4 . . ?
N4 C18 H18A 108.4 . . ?
C19 C18 H18B 108.4 . . ?
N4 C18 H18B 108.4 . . ?
H18A C18 H18B 107.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N4 C20 C21 116.8(15) . . ?
N4 C20 H20A 108.1 . . ?
C21 C20 H20A 108.1 . . ?
N4 C20 H20B 108.1 . . ?
C21 C20 H20B 108.1 . . ?
H20A C20 H20B 107.3 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N1 Co1 O1 92.5(5) . . ?
N1 Co1 N8 89.8(6) . . ?
O1 Co1 N8 87.6(4) . . ?
N1 Co1 N5 89.9(5) . . ?
O1 Co1 N5 90.6(5) . . ?
N8 Co1 N5 178.2(5) . . ?
N1 Co1 N11 171.9(6) . . ?
O1 Co1 N11 79.3(5) . . ?
N8 Co1 N11 89.7(6) . . ?
N5 Co1 N11 90.3(6) . . ?
N1 Co1 N2 87.1(6) . . ?
O1 Co1 N2 179.6(5) . . ?
N8 Co1 N2 92.2(5) . . ?
N5 Co1 N2 89.5(5) . . ?
N11 Co1 N2 101.0(6) . . ?
N3 Co2 N14 106.8(6) . . ?
N3 Co2 N11 136.7(5) . . ?
N14 Co2 N11 113.5(6) . . ?
N3 Co2 O1 85.8(5) . . ?
N14 Co2 O1 98.9(6) . . ?
N11 Co2 O1 73.3(5) . . ?
N3 Co2 N4 81.8(5) . . ?
N14 Co2 N4 100.0(7) . . ?
N11 Co2 N4 105.4(6) . . ?
O1 Co2 N4 159.7(5) . . ?
C8 N1 C9 121.4(14) . . ?
C8 N1 Co1 127.4(11) . . ?
C9 N1 Co1 111.1(11) . . ?
C13 N2 C10 108.1(11) . . ?
C13 N2 C11 109.3(13) . . ?
C10 N2 C11 108.6(13) . . ?
C13 N2 Co1 114.8(9) . . ?
C10 N2 Co1 101.4(9) . . ?
C11 N2 Co1 114.0(9) . . ?
C15 N3 C16 115.0(13) . . ?
C15 N3 Co2 129.3(11) . . ?
C16 N3 Co2 115.3(10) . . ?
C18 N4 C17 107.9(13) . . ?
C18 N4 C20 114.9(16) . . ?
C17 N4 C20 109.9(14) . . ?
C18 N4 Co2 113.6(13) . . ?
C17 N4 Co2 101.5(10) . . ?
C20 N4 Co2 108.2(9) . . ?
N6 N5 Co1 118.5(11) . . ?
N7 N6 N5 177.8(19) . . ?
N9 N8 Co1 117.6(10) . . ?
N10 N9 N8 179(2) . . ?
N12 N11 Co1 126.5(13) . . ?
N12 N11 Co2 125.0(12) . . ?
Co1 N11 Co2 102.5(7) . . ?
N13 N12 N11 175(3) . . ?
N15 N14 Co2 156(2) . . ?
N14 N15 N16 174(3) . . ?
C1 O1 Co1 126.5(9) . . ?
C1 O1 Co2 130.6(9) . . ?
Co1 O1 Co2 102.1(5) . . ?
C22 O2 H2 109.5 . . ?

_refine_diff_density_max         0.660
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.124

