# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1528877'
_audit_update_record             
;
2017-03-02 deposited with the CCDC.
2017-10-30 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            'C50 H34 Co Fe2 N14 O2'
_chemical_formula_weight         1033.54

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'
Fe Fe 0.3463 0.8444 '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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 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+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   27.352(12)
_cell_length_b                   15.144(7)
_cell_length_c                   13.336(6)
_cell_angle_alpha                90
_cell_angle_beta                 116.222(7)
_cell_angle_gamma                90
_cell_volume                     4956(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    6777
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      27.37

_exptl_crystal_description       rodlike
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_F_000             2108
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.963
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15451
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.578
_diffrn_reflns_theta_max         27.533
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             5571
_reflns_number_gt                4138
_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-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0979P)²+4.1241P] 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         5571
_refine_ls_number_parameters     313
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1695
_refine_ls_wR_factor_gt          0.1533
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.001

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
Fe1 Fe 0.14014(2) 0.06775(3) -0.12308(4) 0.02375(16) Uani 1 1 d . . . . .
Co2 Co 0.0000 0.0000 0.0000 0.02001(17) Uani 1 2 d S . P . .
N6 N 0.01007(11) 0.12782(18) 0.0324(2) 0.0279(6) Uani 1 1 d . . . . .
N2 N 0.19284(11) 0.10460(18) 0.0296(2) 0.0290(6) Uani 1 1 d . . . . .
N4 N 0.04938(11) 0.01011(18) -0.0636(2) 0.0275(6) Uani 1 1 d . . . . .
C12 C 0.08419(13) 0.0324(2) -0.0855(3) 0.0247(6) Uani 1 1 d . . . . .
N1 N 0.20192(11) 0.10167(18) -0.1545(2) 0.0295(6) Uani 1 1 d . . . . .
C11 C 0.11044(13) 0.1874(2) -0.1521(3) 0.0297(7) Uani 1 1 d . . . . .
C13 C 0.09167(13) 0.0382(2) -0.2709(3) 0.0248(6) Uani 1 1 d . . . . .
C14 C 0.16796(15) -0.0525(2) -0.0879(3) 0.0310(7) Uani 1 1 d . . . . .
C6 C 0.24331(13) 0.1258(2) 0.0407(3) 0.0321(7) Uani 1 1 d . . . . .
C8 C 0.27479(16) 0.1538(3) 0.2369(3) 0.0478(10) Uani 1 1 d . . . . .
H8 H 0.3024 0.1699 0.3072 0.057 Uiso 1 1 calc R U . . .
C5 C 0.24858(14) 0.1230(2) -0.0638(3) 0.0334(8) Uani 1 1 d . . . . .
N3 N 0.09346(14) 0.2580(2) -0.1673(3) 0.0451(8) Uani 1 1 d . . . . .
C7 C 0.28516(15) 0.1500(3) 0.1437(3) 0.0444(10) Uani 1 1 d . . . . .
H7 H 0.3200 0.1637 0.1502 0.053 Uiso 1 1 calc R U . . .
C19 C 0.03848(15) 0.3062(2) 0.0794(3) 0.0388(9) Uani 1 1 d . . . . .
C10 C 0.18348(16) 0.1089(2) 0.1197(3) 0.0364(8) Uani 1 1 d . . . . .
H10 H 0.1485 0.0947 0.1119 0.044 Uiso 1 1 calc R U . . .
C16 C 0.02733(16) 0.1594(2) 0.1361(3) 0.0395(9) Uani 1 1 d . . . . .
H16 H 0.0298 0.1210 0.1935 0.047 Uiso 1 1 calc R U . . .
C20 C 0.05504(17) 0.4006(2) 0.1034(4) 0.0439(10) Uani 1 1 d . . . . .
C1 C 0.20237(15) 0.1003(3) -0.2560(3) 0.0352(8) Uani 1 1 d . . . . .
H1 H 0.1700 0.0865 -0.3195 0.042 Uiso 1 1 calc R U . . .
C2 C 0.24837(17) 0.1183(3) -0.2692(3) 0.0467(10) Uani 1 1 d . . . . .
H2 H 0.2474 0.1169 -0.3405 0.056 Uiso 1 1 calc R U . . .
N5 N 0.18463(18) -0.1227(2) -0.0634(3) 0.0579(10) Uani 1 1 d . . . . .
C17 C 0.04170(18) 0.2478(3) 0.1615(3) 0.0454(10) Uani 1 1 d . . . . .
H17 H 0.0537 0.2678 0.2353 0.054 Uiso 1 1 calc R U . . .
C9 C 0.22328(17) 0.1334(3) 0.2243(3) 0.0453(10) Uani 1 1 d . . . . .
H9 H 0.2152 0.1361 0.2858 0.054 Uiso 1 1 calc R U . . .
C15 C 0.00575(16) 0.1845(2) -0.0487(3) 0.0382(9) Uani 1 1 d . . . . .
H15 H -0.0065 0.1631 -0.1220 0.046 Uiso 1 1 calc R U . . .
C18 C 0.01867(18) 0.2728(2) -0.0284(3) 0.0443(10) Uani 1 1 d . . . . .
H18 H 0.0140 0.3106 -0.0879 0.053 Uiso 1 1 calc R U . . .
C4 C 0.29670(15) 0.1420(3) -0.0724(3) 0.0477(10) Uani 1 1 d . . . . .
H4 H 0.3288 0.1568 -0.0087 0.057 Uiso 1 1 calc R U . . .
C23 C 0.0853(2) 0.5782(3) 0.1434(5) 0.0658(15) Uani 1 1 d . . . . .
H23 H 0.0944 0.6383 0.1555 0.079 Uiso 1 1 calc R U . . .
C3 C 0.29596(17) 0.1383(3) -0.1763(4) 0.0548(12) Uani 1 1 d . . . . .
H3 H 0.3280 0.1496 -0.1837 0.066 Uiso 1 1 calc R U . . .
C21 C 0.06878(19) 0.4480(3) 0.0306(4) 0.0517(11) Uani 1 1 d . . . . .
H21 H 0.0674 0.4207 -0.0339 0.062 Uiso 1 1 calc R U . . .
C24 C 0.0723(2) 0.5318(3) 0.2183(5) 0.0785(17) Uani 1 1 d . . . . .
H24 H 0.0740 0.5597 0.2827 0.094 Uiso 1 1 calc R U . . .
C25 C 0.0567(2) 0.4431(3) 0.1966(5) 0.0645(14) Uani 1 1 d . . . . .
H25 H 0.0472 0.4119 0.2464 0.077 Uiso 1 1 calc R U . . .
C22 C 0.0848(2) 0.5372(3) 0.0534(5) 0.0642(14) Uani 1 1 d . . . . .
H22 H 0.0952 0.5684 0.0051 0.077 Uiso 1 1 calc R U . . .
N7 N 0.05941(11) 0.02355(18) -0.3607(2) 0.0264(6) Uani 1 1 d . . . . .
O1 O 0.3114(4) 0.1818(5) 0.5281(9) 0.228(4) 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
Fe1 C13 1.880(3) . ?
Fe1 C12 1.886(3) . ?
Fe1 C14 1.949(4) . ?
Fe1 C11 1.954(4) . ?
Fe1 N1 1.980(3) . ?
Fe1 N2 1.986(3) . ?
Co2 N7 1.885(3) 6_556 ?
Co2 N7 1.885(3) 2_554 ?
Co2 N4 1.892(3) . ?
Co2 N4 1.892(3) 5 ?
Co2 N6 1.976(3) 5 ?
Co2 N6 1.976(3) . ?
N6 C16 1.337(5) . ?
N6 C15 1.344(5) . ?
N2 C10 1.335(4) . ?
N2 C6 1.360(4) . ?
N4 C12 1.163(4) . ?
N1 C5 1.354(4) . ?
N1 C1 1.359(4) . ?
C11 N3 1.148(5) . ?
C13 N7 1.152(4) . ?
C14 N5 1.146(5) . ?
C6 C7 1.393(5) . ?
C6 C5 1.463(5) . ?
C8 C9 1.378(6) . ?
C8 C7 1.394(6) . ?
C5 C4 1.401(5) . ?
C19 C17 1.380(6) . ?
C19 C18 1.388(5) . ?
C19 C20 1.490(5) . ?
C10 C9 1.388(5) . ?
C16 C17 1.393(5) . ?
C20 C25 1.382(6) . ?
C20 C21 1.386(6) . ?
C1 C2 1.373(5) . ?
C2 C3 1.378(6) . ?
C15 C18 1.380(5) . ?
C4 C3 1.378(6) . ?
C23 C22 1.345(8) . ?
C23 C24 1.389(8) . ?
C21 C22 1.411(6) . ?
C24 C25 1.400(7) . ?
N7 Co2 1.885(3) 2_554 ?

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
C13 Fe1 C12 86.12(14) . . ?
C13 Fe1 C14 92.81(14) . . ?
C12 Fe1 C14 87.00(14) . . ?
C13 Fe1 C11 88.54(14) . . ?
C12 Fe1 C11 90.01(14) . . ?
C14 Fe1 C11 176.63(14) . . ?
C13 Fe1 N1 96.43(13) . . ?
C12 Fe1 N1 176.73(12) . . ?
C14 Fe1 N1 90.82(13) . . ?
C11 Fe1 N1 92.10(13) . . ?
C13 Fe1 N2 176.74(12) . . ?
C12 Fe1 N2 96.53(13) . . ?
C14 Fe1 N2 89.23(13) . . ?
C11 Fe1 N2 89.56(13) . . ?
N1 Fe1 N2 81.00(12) . . ?
N7 Co2 N7 180.0(3) 6_556 2_554 ?
N7 Co2 N4 88.96(12) 6_556 . ?
N7 Co2 N4 91.04(12) 2_554 . ?
N7 Co2 N4 91.05(12) 6_556 5 ?
N7 Co2 N4 88.95(12) 2_554 5 ?
N4 Co2 N4 180.0 . 5 ?
N7 Co2 N6 90.36(12) 6_556 5 ?
N7 Co2 N6 89.64(12) 2_554 5 ?
N4 Co2 N6 92.27(11) . 5 ?
N4 Co2 N6 87.73(11) 5 5 ?
N7 Co2 N6 89.64(12) 6_556 . ?
N7 Co2 N6 90.36(12) 2_554 . ?
N4 Co2 N6 87.73(11) . . ?
N4 Co2 N6 92.27(11) 5 . ?
N6 Co2 N6 180.00(3) 5 . ?
C16 N6 C15 117.9(3) . . ?
C16 N6 Co2 121.9(2) . . ?
C15 N6 Co2 119.7(2) . . ?
C10 N2 C6 118.6(3) . . ?
C10 N2 Fe1 126.5(2) . . ?
C6 N2 Fe1 114.8(2) . . ?
C12 N4 Co2 164.2(3) . . ?
N4 C12 Fe1 179.1(3) . . ?
C5 N1 C1 118.3(3) . . ?
C5 N1 Fe1 115.4(2) . . ?
C1 N1 Fe1 126.2(2) . . ?
N3 C11 Fe1 178.9(4) . . ?
N7 C13 Fe1 175.4(3) . . ?
N5 C14 Fe1 177.5(3) . . ?
N2 C6 C7 121.4(3) . . ?
N2 C6 C5 114.3(3) . . ?
C7 C6 C5 124.2(3) . . ?
C9 C8 C7 118.8(3) . . ?
N1 C5 C4 121.6(3) . . ?
N1 C5 C6 114.0(3) . . ?
C4 C5 C6 124.3(3) . . ?
C8 C7 C6 119.2(3) . . ?
C17 C19 C18 116.5(3) . . ?
C17 C19 C20 122.5(4) . . ?
C18 C19 C20 121.0(4) . . ?
N2 C10 C9 122.7(3) . . ?
N6 C16 C17 121.9(4) . . ?
C25 C20 C21 118.5(4) . . ?
C25 C20 C19 121.8(4) . . ?
C21 C20 C19 119.7(4) . . ?
N1 C1 C2 122.5(3) . . ?
C1 C2 C3 118.9(4) . . ?
C19 C17 C16 120.7(4) . . ?
C8 C9 C10 119.2(4) . . ?
N6 C15 C18 122.5(3) . . ?
C15 C18 C19 120.4(4) . . ?
C3 C4 C5 118.5(4) . . ?
C22 C23 C24 120.2(4) . . ?
C4 C3 C2 120.1(4) . . ?
C20 C21 C22 119.9(5) . . ?
C23 C24 C25 119.2(5) . . ?
C20 C25 C24 121.2(5) . . ?
C23 C22 C21 121.0(5) . . ?
C13 N7 Co2 172.6(3) . 2_554 ?

_refine_diff_density_max         1.313
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.108

