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

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

data_20150107bhg_0m
_audit_block_doi                 10.5517/cc1j6phx
_database_code_depnum_ccdc_archive 'CCDC 1406609'
_audit_update_record             
;
2015-06-15 deposited with the CCDC.	2020-10-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        EEC-0
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H36 Co2 N4 O22'
_chemical_formula_weight         850.43

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'
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                   9.1263(12)
_cell_length_b                   9.3577(13)
_cell_length_c                   10.6375(14)
_cell_angle_alpha                79.337(2)
_cell_angle_beta                 87.505(2)
_cell_angle_gamma                71.929(2)
_cell_volume                     848.6(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4305
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      28.40

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             438
_exptl_absorpt_coefficient_mu    1.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7677
_exptl_absorpt_correction_T_max  0.8220
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6080
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         28.40
_reflns_number_total             4203
_reflns_number_gt                3821
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0609P)²+0.2275P] 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     SHELXL
_refine_ls_extinction_coef       0.058(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4203
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.1004
_refine_ls_wR_factor_gt          0.0984
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.62994(18) -0.10851(18) 0.15774(15) 0.0199(3) Uani 1 1 d . . .
C2 C 0.51812(18) -0.07220(17) 0.26437(14) 0.0180(3) Uani 1 1 d . . .
C3 C 0.41128(18) 0.07264(17) 0.25732(15) 0.0195(3) Uani 1 1 d . . .
H3 H 0.4092 0.1483 0.1865 0.023 Uiso 1 1 calc R . .
C4 C 0.30719(17) 0.10444(17) 0.35647(15) 0.0183(3) Uani 1 1 d . . .
C5 C 0.30975(17) -0.00988(17) 0.46099(15) 0.0198(3) Uani 1 1 d . . .
H5 H 0.2397 0.0108 0.5264 0.024 Uiso 1 1 calc R . .
C6 C 0.41584(17) -0.15504(17) 0.46903(14) 0.0181(3) Uani 1 1 d . . .
C7 C 0.52040(18) -0.18506(17) 0.37087(15) 0.0192(3) Uani 1 1 d . . .
H7 H 0.5925 -0.2814 0.3763 0.023 Uiso 1 1 calc R . .
C8 C 0.41690(18) -0.27771(18) 0.58317(14) 0.0192(3) Uani 1 1 d . . .
C9 C 0.19271(17) 0.26159(17) 0.35135(15) 0.0200(3) Uani 1 1 d . . .
C10 C 0.0313(3) 0.9155(3) 0.2753(2) 0.0417(5) Uani 1 1 d . . .
H10A H 0.0099 0.8470 0.3432 0.050 Uiso 1 1 calc R . .
C11 C 0.1405(2) 0.8823(3) 0.1864(2) 0.0415(5) Uani 1 1 d . . .
H11A H 0.2091 0.7865 0.1817 0.050 Uiso 1 1 calc R . .
C12 C 0.0199(2) 1.1278(2) 0.1424(2) 0.0348(4) Uani 1 1 d . . .
H12 H -0.0097 1.2300 0.1028 0.042 Uiso 1 1 calc R . .
Co1 Co 0.0000 0.5000 0.5000 0.01916(11) Uani 1 2 d S . .
Co2 Co 0.5000 0.5000 0.0000 0.01968(11) Uani 1 2 d S . .
N1 N 0.13135(18) 1.0161(2) 0.10436(16) 0.0344(4) Uani 1 1 d . . .
H1 H 0.1935 1.0326 0.0431 0.041 Uiso 1 1 d R . .
N2 N -0.04207(19) 1.0696(2) 0.24602(17) 0.0351(4) Uani 1 1 d . . .
H2 H -0.1225 1.1257 0.2839 0.042 Uiso 1 1 d R . .
O1 O 0.17162(16) 0.35428(15) 0.24664(12) 0.0329(3) Uani 1 1 d . . .
O2 O 0.12423(14) 0.28886(13) 0.45366(11) 0.0260(3) Uani 1 1 d . . .
O3 O 0.29727(14) -0.25953(14) 0.65173(11) 0.0271(3) Uani 1 1 d . . .
O4 O 0.53253(14) -0.39312(14) 0.60487(12) 0.0295(3) Uani 1 1 d . . .
O5 O 0.68965(14) -0.24798(13) 0.15062(12) 0.0263(3) Uani 1 1 d . . .
O6 O 0.65824(16) -0.00015(14) 0.08259(13) 0.0333(3) Uani 1 1 d . . .
O7 O 0.04126(17) 0.40605(16) 0.69502(13) 0.0388(3) Uani 1 1 d . . .
H7A H 0.1313 0.3594 0.7399 0.047 Uiso 1 1 d R . .
H7B H -0.0193 0.4739 0.7339 0.047 Uiso 1 1 d R . .
O8 O 0.20002(16) 0.56480(18) 0.48601(17) 0.0399(4) Uani 1 1 d . . .
H8A H 0.2077 0.6153 0.5498 0.048 Uiso 1 1 d R . .
H8B H 0.2941 0.4998 0.4607 0.048 Uiso 1 1 d R . .
O9 O 0.30059(17) 0.43052(17) 0.02514(13) 0.0341(3) Uani 1 1 d . . .
H9A H 0.2683 0.4024 0.1097 0.041 Uiso 1 1 d R . .
H9B H 0.2974 0.3612 -0.0226 0.041 Uiso 1 1 d R . .
O10 O 0.46816(15) 0.58736(13) 0.17249(11) 0.0263(3) Uani 1 1 d . . .
H10C H 0.5300 0.6436 0.1814 0.032 Uiso 1 1 d R . .
H10B H 0.4692 0.5328 0.2454 0.032 Uiso 1 1 d R . .
O11 O 0.36420(16) 0.70730(14) -0.09676(12) 0.0321(3) Uani 1 1 d . . .
H11C H 0.3491 0.7167 -0.1784 0.038 Uiso 1 1 d R . .
H11B H 0.3587 0.7997 -0.0862 0.038 Uiso 1 1 d 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
C1 O6 1.256(2) . ?
C1 O5 1.2641(19) . ?
C1 C2 1.507(2) . ?
C2 C3 1.394(2) . ?
C2 C7 1.395(2) . ?
C3 C4 1.399(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(2) . ?
C4 C9 1.510(2) . ?
C5 C6 1.392(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.391(2) . ?
C6 C8 1.507(2) . ?
C7 H7 0.9300 . ?
C8 O4 1.2470(19) . ?
C8 O3 1.2706(19) . ?
C9 O2 1.2589(19) . ?
C9 O1 1.260(2) . ?
C10 C11 1.349(3) . ?
C10 N2 1.371(3) . ?
C10 H10A 0.9300 . ?
C11 N1 1.369(3) . ?
C11 H11A 0.9300 . ?
C12 N2 1.322(3) . ?
C12 N1 1.323(3) . ?
C12 H12 0.9300 . ?
Co1 O8 2.0861(14) . ?
Co1 O8 2.0861(14) 2_566 ?
Co1 O2 2.0866(11) . ?
Co1 O2 2.0866(11) 2_566 ?
Co1 O7 2.0990(14) 2_566 ?
Co1 O7 2.0990(14) . ?
Co2 O11 2.0589(12) 2_665 ?
Co2 O11 2.0589(12) . ?
Co2 O9 2.1055(14) 2_665 ?
Co2 O9 2.1055(14) . ?
Co2 O10 2.1167(12) 2_665 ?
Co2 O10 2.1167(12) . ?
N1 H1 0.8685 . ?
N2 H2 0.8883 . ?
O7 H7A 0.9101 . ?
O7 H7B 0.8600 . ?
O8 H8A 0.9123 . ?
O8 H8B 0.9468 . ?
O9 H9A 0.9503 . ?
O9 H9B 0.9022 . ?
O10 H10C 0.9010 . ?
O10 H10B 0.8446 . ?
O11 H11C 0.8694 . ?
O11 H11B 0.8778 . ?

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
O6 C1 O5 124.35(14) . . ?
O6 C1 C2 118.69(13) . . ?
O5 C1 C2 116.96(14) . . ?
C3 C2 C7 119.52(14) . . ?
C3 C2 C1 120.75(14) . . ?
C7 C2 C1 119.72(13) . . ?
C2 C3 C4 120.18(14) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 119.52(14) . . ?
C5 C4 C9 119.68(13) . . ?
C3 C4 C9 120.79(14) . . ?
C4 C5 C6 120.81(14) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 119.28(14) . . ?
C7 C6 C8 120.64(13) . . ?
C5 C6 C8 120.08(13) . . ?
C6 C7 C2 120.67(14) . . ?
C6 C7 H7 119.7 . . ?
C2 C7 H7 119.7 . . ?
O4 C8 O3 122.96(14) . . ?
O4 C8 C6 119.15(13) . . ?
O3 C8 C6 117.87(14) . . ?
O2 C9 O1 125.04(14) . . ?
O2 C9 C4 116.46(14) . . ?
O1 C9 C4 118.50(14) . . ?
C11 C10 N2 106.67(19) . . ?
C11 C10 H10A 126.7 . . ?
N2 C10 H10A 126.7 . . ?
C10 C11 N1 107.19(18) . . ?
C10 C11 H11A 126.4 . . ?
N1 C11 H11A 126.4 . . ?
N2 C12 N1 108.48(19) . . ?
N2 C12 H12 125.8 . . ?
N1 C12 H12 125.8 . . ?
O8 Co1 O8 180.00(7) . 2_566 ?
O8 Co1 O2 90.11(5) . . ?
O8 Co1 O2 89.89(5) 2_566 . ?
O8 Co1 O2 89.89(5) . 2_566 ?
O8 Co1 O2 90.11(5) 2_566 2_566 ?
O2 Co1 O2 180.000(1) . 2_566 ?
O8 Co1 O7 87.88(7) . 2_566 ?
O8 Co1 O7 92.12(7) 2_566 2_566 ?
O2 Co1 O7 90.23(5) . 2_566 ?
O2 Co1 O7 89.77(5) 2_566 2_566 ?
O8 Co1 O7 92.12(7) . . ?
O8 Co1 O7 87.88(7) 2_566 . ?
O2 Co1 O7 89.77(5) . . ?
O2 Co1 O7 90.23(5) 2_566 . ?
O7 Co1 O7 180.0 2_566 . ?
O11 Co2 O11 180.00(7) 2_665 . ?
O11 Co2 O9 87.87(6) 2_665 2_665 ?
O11 Co2 O9 92.13(6) . 2_665 ?
O11 Co2 O9 92.13(6) 2_665 . ?
O11 Co2 O9 87.87(6) . . ?
O9 Co2 O9 180.0 2_665 . ?
O11 Co2 O10 90.20(5) 2_665 2_665 ?
O11 Co2 O10 89.80(5) . 2_665 ?
O9 Co2 O10 93.14(5) 2_665 2_665 ?
O9 Co2 O10 86.86(5) . 2_665 ?
O11 Co2 O10 89.80(5) 2_665 . ?
O11 Co2 O10 90.20(5) . . ?
O9 Co2 O10 86.86(5) 2_665 . ?
O9 Co2 O10 93.14(5) . . ?
O10 Co2 O10 180.00(7) 2_665 . ?
C12 N1 C11 108.70(17) . . ?
C12 N1 H1 122.6 . . ?
C11 N1 H1 128.2 . . ?
C12 N2 C10 108.97(17) . . ?
C12 N2 H2 122.3 . . ?
C10 N2 H2 128.7 . . ?
C9 O2 Co1 128.37(11) . . ?
Co1 O7 H7A 130.7 . . ?
Co1 O7 H7B 104.4 . . ?
H7A O7 H7B 110.3 . . ?
Co1 O8 H8A 111.9 . . ?
Co1 O8 H8B 120.9 . . ?
H8A O8 H8B 115.5 . . ?
Co2 O9 H9A 118.7 . . ?
Co2 O9 H9B 114.2 . . ?
H9A O9 H9B 110.0 . . ?
Co2 O10 H10C 113.9 . . ?
Co2 O10 H10B 123.5 . . ?
H10C O10 H10B 104.6 . . ?
Co2 O11 H11C 118.1 . . ?
Co2 O11 H11B 128.8 . . ?
H11C O11 H11B 104.3 . . ?

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
O6 C1 C2 C3 21.0(2) . . . . ?
O5 C1 C2 C3 -159.24(15) . . . . ?
O6 C1 C2 C7 -159.64(16) . . . . ?
O5 C1 C2 C7 20.1(2) . . . . ?
C7 C2 C3 C4 0.0(2) . . . . ?
C1 C2 C3 C4 179.43(14) . . . . ?
C2 C3 C4 C5 -0.9(2) . . . . ?
C2 C3 C4 C9 178.87(14) . . . . ?
C3 C4 C5 C6 0.8(2) . . . . ?
C9 C4 C5 C6 -178.94(14) . . . . ?
C4 C5 C6 C7 0.1(2) . . . . ?
C4 C5 C6 C8 -179.98(14) . . . . ?
C5 C6 C7 C2 -1.0(2) . . . . ?
C8 C6 C7 C2 179.12(14) . . . . ?
C3 C2 C7 C6 0.9(2) . . . . ?
C1 C2 C7 C6 -178.50(14) . . . . ?
C7 C6 C8 O4 17.0(2) . . . . ?
C5 C6 C8 O4 -162.92(15) . . . . ?
C7 C6 C8 O3 -161.58(15) . . . . ?
C5 C6 C8 O3 18.5(2) . . . . ?
C5 C4 C9 O2 12.9(2) . . . . ?
C3 C4 C9 O2 -166.88(15) . . . . ?
C5 C4 C9 O1 -166.51(15) . . . . ?
C3 C4 C9 O1 13.7(2) . . . . ?
N2 C10 C11 N1 -0.3(3) . . . . ?
N2 C12 N1 C11 0.1(2) . . . . ?
C10 C11 N1 C12 0.1(3) . . . . ?
N1 C12 N2 C10 -0.3(2) . . . . ?
C11 C10 N2 C12 0.4(3) . . . . ?
O1 C9 O2 Co1 -16.3(3) . . . . ?
C4 C9 O2 Co1 164.33(11) . . . . ?
O8 Co1 O2 C9 -63.51(15) . . . . ?
O8 Co1 O2 C9 116.49(15) 2_566 . . . ?
O2 Co1 O2 C9 -136(100) 2_566 . . . ?
O7 Co1 O2 C9 24.37(15) 2_566 . . . ?
O7 Co1 O2 C9 -155.63(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        28.40
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.073
