# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

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

data_416a
_database_code_depnum_ccdc_archive 'CCDC 1864421'
_audit_update_record             
;
2018-08-29 deposited with the CCDC.
2018-10-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H25 Co1.50 N2 O11'
_chemical_formula_weight         569.83

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.1175(2)
_cell_length_b                   10.6294(3)
_cell_length_c                   12.5269(4)
_cell_angle_alpha                69.693(3)
_cell_angle_beta                 75.801(2)
_cell_angle_gamma                82.165(2)
_cell_volume                     1222.91(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    15978
_cell_measurement_theta_min      3.37
_cell_measurement_theta_max      29.07

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             587
_exptl_absorpt_coefficient_mu    1.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.778
_exptl_absorpt_correction_T_max  0.822
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15978
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.37
_diffrn_reflns_theta_max         29.07
_reflns_number_total             5713
_reflns_number_gt                4837
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1997)'
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL-PLUS (Sheldrick, 1990)'
_computing_publication_material  SHELXL-97

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5713
_refine_ls_number_parameters     352
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1512
_refine_ls_wR_factor_gt          0.1403
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          1.337
_refine_ls_shift/su_mean         0.100

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 1.0000 0.5000 0.5000 0.02432(15) Uani 1 2 d S . .
Co2 Co 1.62563(3) 1.27041(3) 0.27945(3) 0.02149(13) Uani 1 1 d . . .
O7 O 1.55743(19) 1.3055(2) 0.43770(15) 0.0311(4) Uani 1 1 d D . .
O3 O 1.48019(17) 1.13643(18) 0.30877(17) 0.0300(4) Uani 1 1 d . . .
O6 O 1.26280(18) 0.69265(18) 0.43139(17) 0.0292(4) Uani 1 1 d . . .
N1 N 1.7008(2) 1.2545(2) 0.10843(19) 0.0293(5) Uani 1 1 d . . .
O4 O 1.34576(19) 1.31877(18) 0.30319(16) 0.0285(4) Uani 1 1 d . . .
O5 O 1.04364(18) 0.70021(17) 0.42609(17) 0.0307(4) Uani 1 1 d . . .
O9 O 1.2066(2) 0.4383(2) 0.46266(19) 0.0360(5) Uani 1 1 d D . .
O8 O 0.9673(2) 0.5037(2) 0.33614(18) 0.0373(5) Uani 1 1 d D . .
N2 N 1.6154(2) 1.4702(2) 0.16940(18) 0.0267(5) Uani 1 1 d . . .
C9 C 1.1516(2) 0.7545(2) 0.4172(2) 0.0211(5) Uani 1 1 d . . .
C4 C 1.0159(2) 0.9748(2) 0.3687(2) 0.0214(5) Uani 1 1 d . . .
H4A H 0.9400 0.9273 0.3804 0.026 Uiso 1 1 calc R . .
C1 C 1.2419(2) 1.1172(2) 0.33558(19) 0.0190(5) Uani 1 1 d . . .
C19 C 1.5678(3) 1.5755(3) 0.2067(2) 0.0313(6) Uani 1 1 d . . .
H19A H 1.5391 1.5595 0.2865 0.038 Uiso 1 1 calc R . .
C7 C 1.3628(2) 1.1967(2) 0.31556(19) 0.0203(5) Uani 1 1 d . . .
C15 C 1.6568(3) 1.4914(3) 0.0545(2) 0.0291(6) Uani 1 1 d . . .
C10 C 1.7431(3) 1.1402(3) 0.0840(3) 0.0363(6) Uani 1 1 d . . .
H10A H 1.7360 1.0595 0.1455 0.044 Uiso 1 1 calc R . .
C18 C 1.5592(3) 1.7064(3) 0.1327(3) 0.0377(7) Uani 1 1 d . . .
C14 C 1.7088(3) 1.3721(3) 0.0195(2) 0.0304(6) Uani 1 1 d . . .
C5 C 1.1412(2) 0.9053(2) 0.3834(2) 0.0205(5) Uani 1 1 d . . .
C11 C 1.7965(3) 1.1360(3) -0.0274(3) 0.0394(7) Uani 1 1 d . . .
C2 C 1.1158(2) 1.1847(2) 0.3217(2) 0.0209(5) Uani 1 1 d . . .
H2A H 1.1069 1.2778 0.3022 0.025 Uiso 1 1 calc R . .
C6 C 1.2531(2) 0.9773(2) 0.3664(2) 0.0211(5) Uani 1 1 d . . .
H6A H 1.3370 0.9318 0.3757 0.025 Uiso 1 1 calc R . .
C13 C 1.7607(4) 1.3760(3) -0.0940(3) 0.0465(8) Uani 1 1 d . . .
H13A H 1.7646 1.4575 -0.1545 0.056 Uiso 1 1 calc R . .
C12 C 1.8065(4) 1.2586(4) -0.1169(3) 0.0500(9) Uani 1 1 d . . .
H12A H 1.8447 1.2611 -0.1931 0.060 Uiso 1 1 calc R . .
C17 C 1.6003(4) 1.7257(3) 0.0148(3) 0.0470(8) Uani 1 1 d . . .
H17A H 1.5943 1.8117 -0.0383 0.056 Uiso 1 1 calc R . .
C16 C 1.6497(4) 1.6202(3) -0.0245(3) 0.0442(8) Uani 1 1 d . . .
H16A H 1.6784 1.6345 -0.1040 0.053 Uiso 1 1 calc R . .
C21 C 1.8426(4) 1.0048(4) -0.0494(3) 0.0588(10) Uani 1 1 d . . .
H21A H 1.8774 1.0216 -0.1313 0.088 Uiso 1 1 calc R . .
H21B H 1.7667 0.9484 -0.0231 0.088 Uiso 1 1 calc R . .
H21C H 1.9132 0.9607 -0.0079 0.088 Uiso 1 1 calc R . .
C20 C 1.5051(4) 1.8208(3) 0.1794(3) 0.0503(8) Uani 1 1 d . . .
H20A H 1.5075 1.9037 0.1157 0.076 Uiso 1 1 calc R . .
H20B H 1.5606 1.8254 0.2299 0.076 Uiso 1 1 calc R . .
H20C H 1.4127 1.8062 0.2223 0.076 Uiso 1 1 calc R . .
O1W O 1.6187(3) 0.8866(3) 0.4014(3) 0.0658(8) Uani 1 1 d D . .
O2W O 0.8535(4) 0.7688(4) 0.2652(4) 0.0984(11) Uani 1 1 d D . .
C3 C 1.0034(2) 1.1135(2) 0.3370(2) 0.0215(5) Uani 1 1 d . . .
C8 C 0.8672(2) 1.1860(3) 0.3206(2) 0.0239(5) Uani 1 1 d . . .
O1 O 0.76892(18) 1.11515(19) 0.33444(17) 0.0324(4) Uani 1 1 d . . .
O2 O 0.85107(19) 1.31003(18) 0.29407(18) 0.0333(4) Uani 1 1 d . . .
H7 H 1.677(2) 0.8149(19) 0.405(3) 0.040 Uiso 1 1 d D . .
H1 H 1.620(2) 1.302(3) 0.472(2) 0.040 Uiso 1 1 d D . .
H5 H 1.249(3) 0.509(2) 0.444(2) 0.040 Uiso 1 1 d D . .
H2 H 1.499(2) 1.251(3) 0.484(2) 0.040 Uiso 1 1 d D . .
H6 H 1.240(3) 0.402(2) 0.4105(19) 0.040 Uiso 1 1 d D . .
H3 H 0.931(3) 0.5807(13) 0.308(3) 0.040 Uiso 1 1 d D . .
H4 H 0.927(3) 0.4472(19) 0.326(3) 0.040 Uiso 1 1 d D . .
H8 H 1.666(3) 0.937(2) 0.417(3) 0.040 Uiso 1 1 d D . .
H9 H 0.836(3) 0.723(3) 0.226(3) 0.040 Uiso 1 1 d D . .
H10 H 0.7761(17) 0.798(3) 0.297(3) 0.040 Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O5 2.0662(17) 2_766 ?
Co1 O5 2.0662(17) . ?
Co1 O9 2.092(2) 2_766 ?
Co1 O9 2.092(2) . ?
Co1 O8 2.144(2) 2_766 ?
Co1 O8 2.144(2) . ?
Co2 O3 2.0668(17) . ?
Co2 O7 2.0776(19) . ?
Co2 O1 2.0852(19) 1_655 ?
Co2 N2 2.098(2) . ?
Co2 N1 2.148(2) . ?
O3 C7 1.269(3) . ?
O6 C9 1.243(3) . ?
N1 C10 1.343(4) . ?
N1 C14 1.351(3) . ?
O4 C7 1.245(3) . ?
O5 C9 1.268(3) . ?
N2 C15 1.343(3) . ?
N2 C19 1.345(3) . ?
C9 C5 1.505(3) . ?
C4 C3 1.384(4) . ?
C4 C5 1.398(3) . ?
C1 C6 1.396(3) . ?
C1 C2 1.395(3) . ?
C1 C7 1.502(3) . ?
C19 C18 1.383(4) . ?
C15 C16 1.388(4) . ?
C15 C14 1.473(4) . ?
C10 C11 1.381(4) . ?
C18 C17 1.381(4) . ?
C18 C20 1.510(4) . ?
C14 C13 1.377(4) . ?
C5 C6 1.384(3) . ?
C11 C12 1.390(5) . ?
C11 C21 1.505(5) . ?
C2 C3 1.389(3) . ?
C13 C12 1.371(5) . ?
C17 C16 1.364(5) . ?
C3 C8 1.508(3) . ?
C8 O2 1.241(3) . ?
C8 O1 1.271(3) . ?
O1 Co2 2.0852(19) 1_455 ?

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
O5 Co1 O5 180.00(12) 2_766 . ?
O5 Co1 O9 91.76(8) 2_766 2_766 ?
O5 Co1 O9 88.24(8) . 2_766 ?
O5 Co1 O9 88.24(8) 2_766 . ?
O5 Co1 O9 91.76(8) . . ?
O9 Co1 O9 180.000(1) 2_766 . ?
O5 Co1 O8 89.10(8) 2_766 2_766 ?
O5 Co1 O8 90.90(8) . 2_766 ?
O9 Co1 O8 93.45(9) 2_766 2_766 ?
O9 Co1 O8 86.55(9) . 2_766 ?
O5 Co1 O8 90.90(8) 2_766 . ?
O5 Co1 O8 89.10(8) . . ?
O9 Co1 O8 86.55(9) 2_766 . ?
O9 Co1 O8 93.45(9) . . ?
O8 Co1 O8 180.0 2_766 . ?
O3 Co2 O7 95.85(8) . . ?
O3 Co2 O1 91.99(7) . 1_655 ?
O7 Co2 O1 96.35(8) . 1_655 ?
O3 Co2 N2 122.74(8) . . ?
O7 Co2 N2 98.04(8) . . ?
O1 Co2 N2 140.43(8) 1_655 . ?
O3 Co2 N1 88.70(8) . . ?
O7 Co2 N1 174.38(8) . . ?
O1 Co2 N1 86.75(8) 1_655 . ?
N2 Co2 N1 76.68(9) . . ?
C7 O3 Co2 109.42(15) . . ?
C10 N1 C14 118.6(2) . . ?
C10 N1 Co2 125.82(19) . . ?
C14 N1 Co2 115.53(19) . . ?
C9 O5 Co1 128.72(16) . . ?
C15 N2 C19 119.1(2) . . ?
C15 N2 Co2 116.67(18) . . ?
C19 N2 Co2 124.25(18) . . ?
O6 C9 O5 124.7(2) . . ?
O6 C9 C5 119.4(2) . . ?
O5 C9 C5 115.8(2) . . ?
C3 C4 C5 120.7(2) . . ?
C6 C1 C2 119.2(2) . . ?
C6 C1 C7 121.5(2) . . ?
C2 C1 C7 119.3(2) . . ?
N2 C19 C18 123.5(3) . . ?
O4 C7 O3 122.2(2) . . ?
O4 C7 C1 119.7(2) . . ?
O3 C7 C1 118.0(2) . . ?
N2 C15 C16 120.4(3) . . ?
N2 C15 C14 116.3(2) . . ?
C16 C15 C14 123.3(3) . . ?
N1 C10 C11 123.6(3) . . ?
C17 C18 C19 116.6(3) . . ?
C17 C18 C20 122.2(3) . . ?
C19 C18 C20 121.2(3) . . ?
N1 C14 C13 121.2(3) . . ?
N1 C14 C15 114.7(2) . . ?
C13 C14 C15 124.1(3) . . ?
C6 C5 C4 119.0(2) . . ?
C6 C5 C9 121.6(2) . . ?
C4 C5 C9 119.4(2) . . ?
C12 C11 C10 116.6(3) . . ?
C12 C11 C21 122.2(3) . . ?
C10 C11 C21 121.2(3) . . ?
C3 C2 C1 120.3(2) . . ?
C5 C6 C1 121.0(2) . . ?
C14 C13 C12 119.3(3) . . ?
C11 C12 C13 120.6(3) . . ?
C16 C17 C18 120.8(3) . . ?
C17 C16 C15 119.8(3) . . ?
C2 C3 C4 119.9(2) . . ?
C2 C3 C8 120.6(2) . . ?
C4 C3 C8 119.5(2) . . ?
O2 C8 O1 120.9(2) . . ?
O2 C8 C3 121.6(2) . . ?
O1 C8 C3 117.5(2) . . ?
C8 O1 Co2 98.49(16) . 1_455 ?

_diffrn_measured_fraction_theta_max 0.871
_diffrn_reflns_theta_full        29.07
_diffrn_measured_fraction_theta_full 0.871
_refine_diff_density_max         0.664
_refine_diff_density_min         -0.567
_refine_diff_density_rms         0.074
