# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 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_bjp428m
_database_code_depnum_ccdc_archive 'CCDC 1864042'
_audit_update_record             
;
2018-08-27 deposited with the CCDC.
2019-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H18 Co N4 O6'
_chemical_formula_weight         541.37

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/c'
_space_group_name_Hall           '-P 2yc'

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

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

_cell_length_a                   12.625(4)
_cell_length_b                   9.350(3)
_cell_length_c                   26.835(7)
_cell_angle_alpha                90
_cell_angle_beta                 107.011(12)
_cell_angle_gamma                90
_cell_volume                     3029.1(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3165
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      28.13

_exptl_crystal_description       PLATES
_exptl_crystal_colour            RED
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_F_000             1108
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.607
_shelx_estimated_absorpt_T_min   0.888
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.8883
_exptl_absorpt_correction_T_max  0.9645
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11097
_diffrn_reflns_av_unetI/netI     0.0740
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.587
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             5260
_reflns_number_gt                4077
_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       'BRUKER SMART'
_computing_cell_refinement       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 -0.009 0.033 0.114 25.7 -0.2
2 1.009 0.033 0.386 25.9 -0.3
3 -0.009 -0.033 0.614 26.0 -0.1
4 1.009 -0.033 0.886 26.2 -0.1
5 0.498 0.456 0.750 400.5 94.5
6 0.870 0.195 0.165 8.6 -0.1
7 0.130 0.195 0.335 8.1 -0.2
8 0.503 0.546 0.250 399.4 98.3
9 0.876 0.822 0.663 7.6 0.2
10 0.124 0.822 0.837 7.2 0.0
_platon_squeeze_details          
; ?
;
_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     
'w=1/[σ²(Fo²)+(0.0870P)²+0.8391P] 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         5260
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0716
_refine_ls_wR_factor_ref         0.1699
_refine_ls_wR_factor_gt          0.1630
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_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
Co1 Co 0.09061(4) 0.39322(6) -0.03893(2) 0.01523(19) Uani 1 1 d . . . . .
O1 O 0.1342(2) 0.3704(3) 0.03837(12) 0.0246(7) Uani 1 1 d . . . . .
O2 O 0.0008(2) 0.4354(3) 0.07235(12) 0.0257(7) Uani 1 1 d . . . . .
O3 O 0.3173(3) 0.0761(5) 0.25674(15) 0.0584(12) Uani 1 1 d . . . . .
O4 O 0.1938(2) -0.1995(3) 0.44965(12) 0.0238(7) Uani 1 1 d . . . . .
O5 O 0.0913(2) -0.3258(3) 0.38550(12) 0.0264(7) Uani 1 1 d . . . . .
O6 O 0.5592(3) 1.0805(4) -0.09994(16) 0.0525(12) Uani 1 1 d . . . . .
N1 N 0.2368(3) 0.5223(4) -0.02682(14) 0.0207(8) Uani 1 1 d . . . . .
N2 N 0.5343(3) 0.8659(4) -0.03935(16) 0.0284(10) Uani 1 1 d . . . . .
N3 N 0.6332(3) 0.9371(4) -0.03081(15) 0.0235(9) Uani 1 1 d . . . . .
H3C H 0.690880 0.914781 -0.004399 0.028 Uiso 1 1 calc R U . . .
N4 N 0.9467(3) 1.2612(4) -0.04679(14) 0.0195(8) Uani 1 1 d . . . . .
C1 C 0.0889(3) 0.3719(4) 0.07438(18) 0.0214(10) Uani 1 1 d . . . . .
C2 C 0.1454(3) 0.2903(4) 0.12212(17) 0.0228(10) Uani 1 1 d . . . . .
C3 C 0.2448(4) 0.2223(5) 0.12704(18) 0.0298(11) Uani 1 1 d . . . . .
H3 H 0.276855 0.227269 0.099170 0.036 Uiso 1 1 calc R U . . .
C4 C 0.2989(4) 0.1472(5) 0.1714(2) 0.0356(12) Uani 1 1 d . . . . .
H4 H 0.366499 0.099166 0.173768 0.043 Uiso 1 1 calc R U . . .
C5 C 0.2539(4) 0.1426(6) 0.2121(2) 0.0379(13) Uani 1 1 d . . . . .
C6 C 0.1553(4) 0.2105(7) 0.2089(2) 0.0514(16) Uani 1 1 d . . . . .
H6 H 0.124918 0.207750 0.237386 0.062 Uiso 1 1 calc R U . . .
C7 C 0.1009(4) 0.2831(6) 0.1635(2) 0.0415(14) Uani 1 1 d . . . . .
H7 H 0.032117 0.328509 0.160772 0.050 Uiso 1 1 calc R U . . .
C8 C 0.2686(4) 0.0104(6) 0.2904(2) 0.0398(13) Uani 1 1 d . . . . .
C9 C 0.3245(4) 0.0230(5) 0.34252(19) 0.0291(11) Uani 1 1 d . . . . .
H9 H 0.388988 0.080973 0.353621 0.035 Uiso 1 1 calc R U . . .
C10 C 0.2858(3) -0.0498(5) 0.37857(18) 0.0260(11) Uani 1 1 d . . . . .
H10 H 0.323522 -0.039875 0.414647 0.031 Uiso 1 1 calc R U . . .
C11 C 0.1934(4) -0.1367(5) 0.36311(18) 0.0261(11) Uani 1 1 d . . . . .
C12 C 0.1374(4) -0.1465(6) 0.3101(2) 0.0423(14) Uani 1 1 d . . . . .
H12 H 0.072531 -0.203508 0.298765 0.051 Uiso 1 1 calc R U . . .
C13 C 0.1758(5) -0.0739(7) 0.2742(2) 0.0577(18) Uani 1 1 d . . . . .
H13 H 0.137906 -0.082176 0.238058 0.069 Uiso 1 1 calc R U . . .
C14 C 0.1567(3) -0.2235(4) 0.40113(18) 0.0208(10) Uani 1 1 d . . . . .
C15 C 0.2500(4) 0.6065(5) -0.0644(2) 0.0341(12) Uani 1 1 d . . . . .
H15 H 0.192535 0.609037 -0.096524 0.041 Uiso 1 1 calc R U . . .
C16 C 0.3424(4) 0.6907(5) -0.0596(2) 0.0334(12) Uani 1 1 d . . . . .
H16 H 0.347700 0.749188 -0.087704 0.040 Uiso 1 1 calc R U . . .
C17 C 0.4279(3) 0.6887(4) -0.01288(18) 0.0219(10) Uani 1 1 d . . . . .
C18 C 0.4143(3) 0.6025(5) 0.02590(18) 0.0286(11) Uani 1 1 d . . . . .
H18 H 0.470496 0.597689 0.058371 0.034 Uiso 1 1 calc R U . . .
C19 C 0.3184(3) 0.5222(5) 0.01779(18) 0.0256(11) Uani 1 1 d . . . . .
H19 H 0.310622 0.463917 0.045505 0.031 Uiso 1 1 calc R U . . .
C20 C 0.5294(3) 0.7737(5) -0.00540(19) 0.0253(11) Uani 1 1 d . . . . .
H20 H 0.590823 0.759676 0.024638 0.030 Uiso 1 1 calc R U . . .
C21 C 0.6387(4) 1.0428(5) -0.06444(19) 0.0282(11) Uani 1 1 d . . . . .
C22 C 0.7501(3) 1.1129(5) -0.05627(19) 0.0248(10) Uani 1 1 d . . . . .
C23 C 0.7598(4) 1.2062(5) -0.0945(2) 0.0323(12) Uani 1 1 d . . . . .
H23 H 0.698972 1.222071 -0.124680 0.039 Uiso 1 1 calc R U . . .
C24 C 0.8586(4) 1.2760(5) -0.08852(19) 0.0300(11) Uani 1 1 d . . . . .
H24 H 0.864497 1.338210 -0.115569 0.036 Uiso 1 1 calc R U . . .
C25 C 0.9369(3) 1.1690(5) -0.01090(18) 0.0227(10) Uani 1 1 d . . . . .
H25 H 0.999423 1.153825 0.018529 0.027 Uiso 1 1 calc R U . . .
C26 C 0.8408(3) 1.0932(5) -0.01369(18) 0.0253(10) Uani 1 1 d . . . . .
H26 H 0.837790 1.028971 0.013304 0.030 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O1 1.996(3) . ?
Co1 O2 2.024(3) 3_565 ?
Co1 O5 2.126(3) 4 ?
Co1 N1 2.149(3) . ?
Co1 N4 2.155(3) 1_445 ?
Co1 O4 2.303(3) 4 ?
O1 C1 1.258(5) . ?
O2 C1 1.248(5) . ?
O3 C8 1.378(6) . ?
O3 C5 1.379(6) . ?
O4 C14 1.268(5) . ?
O5 C14 1.253(5) . ?
O6 C21 1.217(5) . ?
N1 C15 1.329(6) . ?
N1 C19 1.332(5) . ?
N2 C20 1.269(6) . ?
N2 N3 1.374(5) . ?
N3 C21 1.354(6) . ?
N4 C25 1.326(5) . ?
N4 C24 1.335(5) . ?
C1 C2 1.483(6) . ?
C2 C3 1.379(6) . ?
C2 C7 1.385(6) . ?
C3 C4 1.379(7) . ?
C4 C5 1.370(7) . ?
C5 C6 1.378(7) . ?
C6 C7 1.388(7) . ?
C8 C13 1.373(7) . ?
C8 C9 1.374(7) . ?
C9 C10 1.384(6) . ?
C10 C11 1.382(6) . ?
C11 C12 1.393(6) . ?
C11 C14 1.480(6) . ?
C12 C13 1.379(7) . ?
C15 C16 1.382(6) . ?
C16 C17 1.394(6) . ?
C17 C18 1.366(6) . ?
C17 C20 1.471(5) . ?
C18 C19 1.387(6) . ?
C21 C22 1.508(6) . ?
C22 C26 1.373(6) . ?
C22 C23 1.380(6) . ?
C23 C24 1.374(6) . ?
C25 C26 1.388(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Co1 O2 119.56(13) . 3_565 ?
O1 Co1 O5 151.98(12) . 4 ?
O2 Co1 O5 88.45(12) 3_565 4 ?
O1 Co1 N1 86.54(13) . . ?
O2 Co1 N1 88.58(12) 3_565 . ?
O5 Co1 N1 93.90(13) 4 . ?
O1 Co1 N4 90.49(13) . 1_445 ?
O2 Co1 N4 93.15(12) 3_565 1_445 ?
O5 Co1 N4 88.59(13) 4 1_445 ?
N1 Co1 N4 177.02(14) . 1_445 ?
O1 Co1 O4 93.41(12) . 4 ?
O2 Co1 O4 146.58(12) 3_565 4 ?
O5 Co1 O4 58.64(11) 4 4 ?
N1 Co1 O4 88.16(12) . 4 ?
N4 Co1 O4 91.72(12) 1_445 4 ?
C1 O1 Co1 138.4(3) . . ?
C1 O2 Co1 141.3(3) . 3_565 ?
C8 O3 C5 121.0(4) . . ?
C14 O4 Co1 86.8(2) . 4_556 ?
C14 O5 Co1 95.4(3) . 4_556 ?
C15 N1 C19 116.6(4) . . ?
C15 N1 Co1 120.7(3) . . ?
C19 N1 Co1 122.7(3) . . ?
C20 N2 N3 116.2(4) . . ?
C21 N3 N2 117.7(4) . . ?
C25 N4 C24 116.4(3) . . ?
C25 N4 Co1 123.8(3) . 1_665 ?
C24 N4 Co1 119.7(3) . 1_665 ?
O2 C1 O1 124.8(4) . . ?
O2 C1 C2 118.6(4) . . ?
O1 C1 C2 116.5(4) . . ?
C3 C2 C7 118.2(4) . . ?
C3 C2 C1 120.9(4) . . ?
C7 C2 C1 120.9(4) . . ?
C2 C3 C4 121.6(4) . . ?
C5 C4 C3 119.2(5) . . ?
C4 C5 C6 120.9(5) . . ?
C4 C5 O3 115.8(5) . . ?
C6 C5 O3 123.0(5) . . ?
C5 C6 C7 119.0(5) . . ?
C2 C7 C6 121.0(5) . . ?
C13 C8 C9 120.7(5) . . ?
C13 C8 O3 123.4(5) . . ?
C9 C8 O3 115.7(5) . . ?
C8 C9 C10 119.1(5) . . ?
C11 C10 C9 121.3(5) . . ?
C10 C11 C12 118.5(4) . . ?
C10 C11 C14 121.5(4) . . ?
C12 C11 C14 120.0(4) . . ?
C13 C12 C11 120.3(5) . . ?
C8 C13 C12 120.1(5) . . ?
O5 C14 O4 119.2(4) . . ?
O5 C14 C11 119.8(4) . . ?
O4 C14 C11 121.0(4) . . ?
N1 C15 C16 123.8(4) . . ?
C15 C16 C17 119.2(4) . . ?
C18 C17 C16 117.2(4) . . ?
C18 C17 C20 120.9(4) . . ?
C16 C17 C20 122.0(4) . . ?
C17 C18 C19 119.9(4) . . ?
N1 C19 C18 123.4(4) . . ?
N2 C20 C17 119.5(4) . . ?
O6 C21 N3 122.8(4) . . ?
O6 C21 C22 120.6(4) . . ?
N3 C21 C22 116.6(4) . . ?
C26 C22 C23 118.1(4) . . ?
C26 C22 C21 125.3(4) . . ?
C23 C22 C21 116.7(4) . . ?
C24 C23 C22 119.2(4) . . ?
N4 C24 C23 123.7(4) . . ?
N4 C25 C26 124.0(4) . . ?
C22 C26 C25 118.6(4) . . ?

_refine_diff_density_max         0.929
_refine_diff_density_min         -0.849
_refine_diff_density_rms         0.097



