# 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_LIFM-WZ-4
_database_code_depnum_ccdc_archive 'CCDC 1873050'
_audit_update_record             
;
2018-10-12 deposited with the CCDC.
2019-01-28 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            'C48 H28  Co N20'
_chemical_formula_weight         943.83

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co -2.3653 3.6143 '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                   12.9310(11)
_cell_length_b                   13.4843(10)
_cell_length_c                   15.6502(11)
_cell_angle_alpha                90
_cell_angle_beta                 101.310(8)
_cell_angle_gamma                90
_cell_volume                     2675.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1678
_cell_measurement_theta_min      4.3410
_cell_measurement_theta_max      64.0010

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_F_000             966
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    2.929
_shelx_estimated_absorpt_T_min   0.606
_shelx_estimated_absorpt_T_max   0.636
_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      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  bruker-CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4321
_diffrn_reflns_av_unetI/netI     0.0660
_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         4.064
_diffrn_reflns_theta_max         63.685
_diffrn_reflns_theta_full        63.685
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             4321
_reflns_number_gt                2519
_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-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0169P)²+8.7819P] 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         4321
_refine_ls_number_parameters     313
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1358
_refine_ls_R_factor_gt           0.0935
_refine_ls_wR_factor_ref         0.2079
_refine_ls_wR_factor_gt          0.1947
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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 0.0000 0.5000 0.5000 0.0654(5) Uani 1 2 d S . P . .
N1 N -0.0404(4) 0.5488(4) 0.3789(3) 0.0671(15) Uani 1 1 d . . . . .
N2 N 0.1354(4) 0.5694(4) 0.5103(3) 0.0686(15) Uani 1 1 d . . . . .
N3 N 0.3994(7) 0.7353(6) 0.0647(5) 0.140(4) Uani 1 1 d . . . . .
N4 N 0.4536(7) 0.7978(6) 0.0212(5) 0.117(3) Uani 1 1 d . U . . .
N5 N 0.4388(5) 0.8885(5) 0.0433(3) 0.0760(16) Uani 1 1 d . U . . .
N6 N 0.3832(5) 0.8846(5) 0.1058(4) 0.0850(19) Uani 1 1 d . . . . .
H6A H 0.3683 0.9344 0.1356 0.102 Uiso 1 1 calc R U . . .
N7 N 0.6530(8) 0.5063(9) 0.9573(6) 0.156(4) Uani 1 1 d . . . . .
N8 N 0.7242(9) 0.5459(11) 1.0230(7) 0.172(5) Uani 1 1 d . . . . .
N9 N 0.6895(9) 0.6327(10) 1.0443(6) 0.148(4) Uani 1 1 d . . . . .
N10 N 0.5969(6) 0.6498(7) 0.9895(5) 0.112(2) Uani 1 1 d . . . . .
H10 H 0.5573 0.7013 0.9879 0.134 Uiso 1 1 calc R U . . .
C1 C -0.1341(6) 0.5330(6) 0.3221(4) 0.077(2) Uani 1 1 d . . . . .
C2 C -0.1315(7) 0.5802(6) 0.2409(4) 0.089(2) Uani 1 1 d . . . . .
H2 H -0.1859 0.5808 0.1922 0.107 Uiso 1 1 calc R U . . .
C3 C -0.0392(6) 0.6224(6) 0.2469(4) 0.084(2) Uani 1 1 d . . . . .
H3 H -0.0163 0.6588 0.2036 0.101 Uiso 1 1 calc R U . . .
C4 C 0.0205(6) 0.6022(6) 0.3328(4) 0.0693(19) Uani 1 1 d . . . . .
C5 C 0.1223(6) 0.6340(6) 0.3625(4) 0.074(2) Uani 1 1 d . . . . .
C6 C 0.1751(6) 0.6173(6) 0.4468(4) 0.081(2) Uani 1 1 d . . . . .
C7 C 0.2809(6) 0.6515(7) 0.4808(5) 0.103(3) Uani 1 1 d . . . . .
H7 H 0.3240 0.6867 0.4505 0.123 Uiso 1 1 calc R U . . .
C8 C 0.3047(7) 0.6234(7) 0.5630(5) 0.102(3) Uani 1 1 d . . . . .
H8 H 0.3678 0.6357 0.6015 0.123 Uiso 1 1 calc R U . . .
C9 C 0.2163(6) 0.5708(6) 0.5824(5) 0.077(2) Uani 1 1 d . . . . .
C10 C 0.2152(6) 0.5237(6) 0.6609(4) 0.074(2) Uani 1 1 d . . . . .
C11 C 0.1812(6) 0.6796(6) 0.2986(4) 0.078(2) Uani 1 1 d . . . . .
C12 C 0.2037(6) 0.6238(7) 0.2319(5) 0.099(3) Uani 1 1 d . . . . .
H12 H 0.1806 0.5584 0.2260 0.119 Uiso 1 1 calc R U . . .
C13 C 0.2597(7) 0.6619(7) 0.1729(5) 0.099(3) Uani 1 1 d . . . . .
H13 H 0.2740 0.6214 0.1285 0.119 Uiso 1 1 calc R U . . .
C14 C 0.2946(6) 0.7575(6) 0.1783(4) 0.078(2) Uani 1 1 d . . . . .
C15 C 0.2728(8) 0.8129(7) 0.2434(5) 0.115(3) Uani 1 1 d . . . . .
H15 H 0.2955 0.8784 0.2491 0.139 Uiso 1 1 calc R U . . .
C16 C 0.2165(8) 0.7733(7) 0.3028(5) 0.116(3) Uani 1 1 d . . . . .
H16 H 0.2028 0.8138 0.3474 0.139 Uiso 1 1 calc R U . . .
C17 C 0.3550(6) 0.7934(6) 0.1150(4) 0.080(2) Uani 1 1 d . . . . .
C18 C 0.3112(7) 0.5361(7) 0.7324(5) 0.083(2) Uani 1 1 d . . . . .
C19 C 0.3802(8) 0.4576(9) 0.7600(7) 0.122(3) Uani 1 1 d . . . . .
H19 H 0.3681 0.3962 0.7329 0.146 Uiso 1 1 calc R U . . .
C20 C 0.4675(8) 0.4705(9) 0.8281(7) 0.120(3) Uani 1 1 d . . . . .
H20 H 0.5122 0.4174 0.8465 0.143 Uiso 1 1 calc R U . . .
C21 C 0.4868(7) 0.5598(8) 0.8667(5) 0.090(2) Uani 1 1 d . . . . .
C22 C 0.4201(8) 0.6379(8) 0.8431(6) 0.111(3) Uani 1 1 d . . . . .
H22 H 0.4316 0.6983 0.8720 0.133 Uiso 1 1 calc R U . . .
C23 C 0.3338(7) 0.6248(7) 0.7741(5) 0.102(3) Uani 1 1 d . . . . .
H23 H 0.2901 0.6788 0.7560 0.123 Uiso 1 1 calc R U . . .
C24 C 0.5797(8) 0.5690(9) 0.9377(6) 0.103(3) 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
Co1 N5 1.885(6) 4_576 ?
Co1 N5 1.885(6) 2_545 ?
Co1 N2 1.964(5) . ?
Co1 N2 1.964(5) 3_566 ?
Co1 N1 1.977(5) 3_566 ?
Co1 N1 1.977(5) . ?
N1 C1 1.371(9) . ?
N1 C4 1.372(8) . ?
N2 C6 1.366(8) . ?
N2 C9 1.381(9) . ?
N3 C17 1.320(9) . ?
N3 N4 1.361(9) . ?
N4 N5 1.296(9) . ?
N5 N6 1.325(6) . ?
N5 Co1 1.885(6) 2 ?
N6 C17 1.298(9) . ?
N6 H6A 0.8600 . ?
N7 C24 1.263(12) . ?
N7 N8 1.348(13) . ?
N8 N9 1.320(14) . ?
N9 N10 1.349(11) . ?
N10 C24 1.351(11) . ?
N10 H10 0.8600 . ?
C1 C10 1.365(9) 3_566 ?
C1 C2 1.428(9) . ?
C2 C3 1.310(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.439(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(10) . ?
C5 C6 1.380(9) . ?
C5 C11 1.501(9) . ?
C6 C7 1.443(10) . ?
C7 C8 1.319(10) . ?
C7 H7 0.9300 . ?
C8 C9 1.427(10) . ?
C8 H8 0.9300 . ?
C9 C10 1.385(9) . ?
C10 C1 1.365(9) 3_566 ?
C10 C18 1.510(11) . ?
C11 C16 1.342(11) . ?
C11 C12 1.364(9) . ?
C12 C13 1.380(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.363(10) . ?
C13 H13 0.9300 . ?
C14 C15 1.336(9) . ?
C14 C17 1.460(9) . ?
C15 C16 1.394(10) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C18 C23 1.366(11) . ?
C18 C19 1.397(12) . ?
C19 C20 1.403(13) . ?
C19 H19 0.9300 . ?
C20 C21 1.349(12) . ?
C20 H20 0.9300 . ?
C21 C22 1.366(12) . ?
C21 C24 1.472(12) . ?
C22 C23 1.403(12) . ?
C22 H22 0.9300 . ?
C23 H23 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
N5 Co1 N5 180.0(3) 4_576 2_545 ?
N5 Co1 N2 91.2(2) 4_576 . ?
N5 Co1 N2 88.8(2) 2_545 . ?
N5 Co1 N2 88.8(2) 4_576 3_566 ?
N5 Co1 N2 91.2(2) 2_545 3_566 ?
N2 Co1 N2 180.00(16) . 3_566 ?
N5 Co1 N1 88.4(2) 4_576 3_566 ?
N5 Co1 N1 91.6(2) 2_545 3_566 ?
N2 Co1 N1 90.9(2) . 3_566 ?
N2 Co1 N1 89.1(2) 3_566 3_566 ?
N5 Co1 N1 91.6(2) 4_576 . ?
N5 Co1 N1 88.4(2) 2_545 . ?
N2 Co1 N1 89.1(2) . . ?
N2 Co1 N1 90.9(2) 3_566 . ?
N1 Co1 N1 180.0 3_566 . ?
C1 N1 C4 105.4(5) . . ?
C1 N1 Co1 127.1(4) . . ?
C4 N1 Co1 127.4(5) . . ?
C6 N2 C9 104.8(6) . . ?
C6 N2 Co1 128.5(5) . . ?
C9 N2 Co1 126.4(4) . . ?
C17 N3 N4 104.9(7) . . ?
N5 N4 N3 109.5(6) . . ?
N4 N5 N6 106.8(6) . . ?
N4 N5 Co1 124.2(4) . 2 ?
N6 N5 Co1 128.6(5) . 2 ?
C17 N6 N5 108.9(6) . . ?
C17 N6 H6A 125.5 . . ?
N5 N6 H6A 125.5 . . ?
C24 N7 N8 106.8(10) . . ?
N9 N8 N7 109.2(10) . . ?
N8 N9 N10 107.1(10) . . ?
C24 N10 N9 105.4(9) . . ?
C24 N10 H10 127.3 . . ?
N9 N10 H10 127.3 . . ?
C10 C1 N1 125.1(6) 3_566 . ?
C10 C1 C2 125.2(7) 3_566 . ?
N1 C1 C2 109.6(6) . . ?
C3 C2 C1 108.1(7) . . ?
C3 C2 H2 126.0 . . ?
C1 C2 H2 126.0 . . ?
C2 C3 C4 107.4(6) . . ?
C2 C3 H3 126.3 . . ?
C4 C3 H3 126.3 . . ?
N1 C4 C5 126.6(6) . . ?
N1 C4 C3 109.5(6) . . ?
C5 C4 C3 123.9(6) . . ?
C4 C5 C6 122.2(6) . . ?
C4 C5 C11 118.6(6) . . ?
C6 C5 C11 118.9(7) . . ?
N2 C6 C5 125.9(7) . . ?
N2 C6 C7 110.4(6) . . ?
C5 C6 C7 123.7(6) . . ?
C8 C7 C6 106.9(7) . . ?
C8 C7 H7 126.6 . . ?
C6 C7 H7 126.6 . . ?
C7 C8 C9 107.9(8) . . ?
C7 C8 H8 126.1 . . ?
C9 C8 H8 126.1 . . ?
N2 C9 C10 125.5(6) . . ?
N2 C9 C8 110.0(6) . . ?
C10 C9 C8 124.4(7) . . ?
C1 C10 C9 124.9(7) 3_566 . ?
C1 C10 C18 117.9(6) 3_566 . ?
C9 C10 C18 117.2(6) . . ?
C16 C11 C12 115.8(7) . . ?
C16 C11 C5 124.4(7) . . ?
C12 C11 C5 119.8(7) . . ?
C11 C12 C13 121.8(8) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C14 C13 C12 121.4(7) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C15 C14 C13 117.4(7) . . ?
C15 C14 C17 123.5(7) . . ?
C13 C14 C17 119.1(6) . . ?
C14 C15 C16 120.7(8) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C11 C16 C15 123.1(8) . . ?
C11 C16 H16 118.5 . . ?
C15 C16 H16 118.5 . . ?
N6 C17 N3 109.4(6) . . ?
N6 C17 C14 126.1(7) . . ?
N3 C17 C14 124.1(7) . . ?
C23 C18 C19 116.9(9) . . ?
C23 C18 C10 121.2(8) . . ?
C19 C18 C10 121.9(8) . . ?
C18 C19 C20 120.8(10) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C21 C20 C19 120.1(10) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C22 C21 C20 121.0(9) . . ?
C22 C21 C24 121.2(10) . . ?
C20 C21 C24 117.8(10) . . ?
C21 C22 C23 118.5(9) . . ?
C21 C22 H22 120.8 . . ?
C23 C22 H22 120.8 . . ?
C18 C23 C22 122.7(9) . . ?
C18 C23 H23 118.7 . . ?
C22 C23 H23 118.7 . . ?
N7 C24 N10 111.5(9) . . ?
N7 C24 C21 126.1(11) . . ?
N10 C24 C21 122.4(11) . . ?

_refine_diff_density_max         0.510
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.077
# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
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
_platon_squeeze_void_content
1 0.000 0.005 0.000 468 54 ' '
2 0.500 0.247 0.500 468 54 ' '
_platon_squeeze_details          
;
;


