# Electronic Supplementary Material (ESI) for ChemComm.
# 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_1_sq_d
_database_code_depnum_ccdc_archive 'CCDC 1843727'
_audit_update_record             
;
2018-05-17 deposited with the CCDC.
2018-07-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        Co-DBPY
_chemical_name_common            Co-DBPY
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H18 Co N4 O7'
_chemical_formula_weight         581.39

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           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

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

_cell_length_a                   11.386(2)
_cell_length_b                   23.961(5)
_cell_length_c                   14.850(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.161(15)
_cell_angle_gamma                90.00
_cell_volume                     3928.5(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2632
_cell_measurement_theta_min      2.5085
_cell_measurement_theta_max      17.592

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.983
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1188
_exptl_absorpt_coefficient_mu    0.473
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.8989
_exptl_absorpt_correction_T_max  0.9113
_exptl_absorpt_process_details   ?

_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            29508
_diffrn_reflns_av_R_equivalents  0.0876
_diffrn_reflns_av_sigmaI/netI    0.1434
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6925
_reflns_number_gt                2609
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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)+(0.0868P)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         6925
_refine_ls_number_parameters     361
_refine_ls_number_restraints     28
_refine_ls_R_factor_all          0.1620
_refine_ls_R_factor_gt           0.0764
_refine_ls_wR_factor_ref         0.2148
_refine_ls_wR_factor_gt          0.1984
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.003
_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
Co1 Co 0.50683(5) 0.41982(3) 0.95140(5) 0.0617(2) Uani 1 1 d U . .
N2 N 0.6946(3) 0.41888(17) 0.9499(3) 0.0679(12) Uani 1 1 d . . .
N1 N 1.3160(3) 0.42267(17) 0.9505(3) 0.0706(13) Uani 1 1 d . . .
C2 C 0.9421(4) 0.4190(2) 0.9495(4) 0.0632(14) Uani 1 1 d . . .
C1 C 1.0713(4) 0.4200(2) 0.9507(4) 0.0673(15) Uani 1 1 d . . .
O1 O 0.4928(3) 0.00968(14) 1.3807(2) 0.0757(10) Uani 1 1 d U . .
O4 O 0.4422(3) -0.07717(14) 1.4092(2) 0.0730(10) Uani 1 1 d . . .
O3 O 0.4938(3) 0.33188(15) 0.9536(3) 0.0926(13) Uani 1 1 d U . .
O2 O 0.4549(4) 0.37053(15) 0.8167(3) 0.0921(11) Uani 1 1 d U . .
C4 C 0.8575(4) 0.4442(3) 0.8832(4) 0.097(2) Uani 1 1 d . . .
H4A H 0.8799 0.4624 0.8347 0.116 Uiso 1 1 calc R . .
N4 N 0.3798(4) 0.03047(19) 1.0361(3) 0.0926(16) Uani 1 1 d . . .
H4B H 0.4210 0.0590 1.0613 0.111 Uiso 1 1 calc R . .
C6 C 1.1585(5) 0.4010(3) 1.0205(4) 0.091(2) Uani 1 1 d . . .
H6A H 1.1375 0.3860 1.0721 0.109 Uiso 1 1 calc R . .
C7 C 1.2777(5) 0.4026(3) 1.0191(4) 0.095(2) Uani 1 1 d . . .
H7A H 1.3345 0.3886 1.0701 0.114 Uiso 1 1 calc R . .
C8 C 0.3753(5) -0.0151(3) 1.0970(4) 0.0815(17) Uani 1 1 d . . .
C9 C 0.7352(5) 0.4433(3) 0.8865(4) 0.096(2) Uani 1 1 d . . .
H9A H 0.6796 0.4617 0.8395 0.116 Uiso 1 1 calc R . .
C10 C 0.3241(6) 0.0800(3) 0.8866(4) 0.097(2) Uani 1 1 d . . .
N3 N 0.3748(5) 0.1321(2) 0.9058(3) 0.1016(17) Uani 1 1 d . . .
H3A H 0.4097 0.1386 0.9630 0.122 Uiso 1 1 calc R . .
C12 C 0.4105(4) -0.0485(2) 1.2534(4) 0.0678(15) Uani 1 1 d . . .
C14 C 0.4130(4) -0.0058(2) 1.1916(4) 0.0719(16) Uani 1 1 d . . .
H14A H 0.4401 0.0294 1.2136 0.086 Uiso 1 1 calc R . .
C15 C 0.7756(5) 0.3929(3) 1.0122(5) 0.136(3) Uani 1 1 d . . .
H15A H 0.7494 0.3752 1.0595 0.164 Uiso 1 1 calc R . .
O5 O 0.2137(7) -0.0448(2) 0.8585(3) 0.194(3) Uani 1 1 d . . .
C18 C 0.4513(4) -0.0377(3) 1.3554(4) 0.0639(15) Uani 1 1 d U . .
C19 C 0.8986(5) 0.3891(4) 1.0146(5) 0.148(3) Uani 1 1 d . . .
H19A H 0.9502 0.3671 1.0588 0.178 Uiso 1 1 calc R . .
C22 C 0.4593(5) 0.3292(3) 0.8651(5) 0.0903(18) Uani 1 1 d U . .
C23 C 1.1114(5) 0.4423(3) 0.8803(5) 0.146(3) Uani 1 1 d U . .
H23A H 1.0559 0.4584 0.8306 0.175 Uiso 1 1 calc R . .
C24 C 0.4148(5) 0.2284(2) 0.8817(4) 0.0913(19) Uani 1 1 d . . .
H24A H 0.4365 0.2327 0.9459 0.110 Uiso 1 1 calc R . .
C25 C 0.3766(7) 0.1764(3) 0.8430(5) 0.108(2) Uani 1 1 d . . .
C26 C 0.3695(6) -0.1010(3) 1.2189(5) 0.110(2) Uani 1 1 d . . .
H26A H 0.3655 -0.1303 1.2591 0.133 Uiso 1 1 calc R . .
C28 C 1.2331(5) 0.4419(3) 0.8802(5) 0.131(3) Uani 1 1 d . . .
H28A H 1.2565 0.4556 0.8286 0.157 Uiso 1 1 calc R . .
C29 C 0.2549(8) 0.0014(3) 0.8691(5) 0.126(3) Uani 1 1 d . . .
C30 C 0.4203(6) 0.2723(3) 0.8263(5) 0.101(2) Uani 1 1 d . . .
C31 C 0.3290(6) 0.0348(2) 0.9459(5) 0.0893(19) Uani 1 1 d . . .
C35 C 0.3479(10) 0.2130(3) 0.6976(6) 0.198(5) Uani 1 1 d . . .
H35A H 0.3236 0.2087 0.6335 0.238 Uiso 1 1 calc R . .
C36 C 0.3444(9) 0.1689(3) 0.7521(6) 0.169(4) Uani 1 1 d . . .
H36A H 0.3201 0.1341 0.7267 0.202 Uiso 1 1 calc R . .
C37 C 0.3316(7) -0.0668(3) 1.0619(5) 0.123(3) Uani 1 1 d . . .
H37A H 0.3014 -0.0724 0.9985 0.148 Uiso 1 1 calc R . .
C39 C 0.3347(7) -0.1086(3) 1.1236(5) 0.130(3) Uani 1 1 d . . .
H39A H 0.3124 -0.1443 1.1010 0.156 Uiso 1 1 calc R . .
C40 C 0.3874(8) 0.2659(3) 0.7345(6) 0.144(3) Uani 1 1 d . . .
H40A H 0.3903 0.2959 0.6952 0.173 Uiso 1 1 calc R . .
O6 O 0.1984(8) 0.0621(2) 0.7296(4) 0.218(4) Uani 1 1 d . . .
C60 C 0.2497(8) 0.0511(3) 0.8073(6) 0.128(3) Uani 1 1 d . . .
O1W O 0.4694(6) 0.86551(19) 0.8848(4) 0.202(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 O1 1.974(3) 4_565 ?
Co1 O4 2.010(4) 2_657 ?
Co1 O3 2.113(4) . ?
Co1 N2 2.144(4) . ?
Co1 N1 2.171(4) 1_455 ?
Co1 O2 2.273(4) . ?
Co1 C22 2.512(7) . ?
N2 C9 1.286(6) . ?
N2 C15 1.295(7) . ?
N1 C7 1.294(6) . ?
N1 C28 1.308(6) . ?
N1 Co1 2.171(4) 1_655 ?
C2 C4 1.340(7) . ?
C2 C19 1.389(8) . ?
C2 C1 1.467(6) . ?
C1 C6 1.329(7) . ?
C1 C23 1.348(8) . ?
O1 C18 1.252(6) . ?
O1 Co1 1.974(3) 4_566 ?
O4 C18 1.258(6) . ?
O4 Co1 2.010(4) 2_647 ?
O3 C22 1.279(7) . ?
O2 C22 1.218(7) . ?
C4 C9 1.406(7) . ?
N4 C31 1.327(7) . ?
N4 C8 1.426(7) . ?
C6 C7 1.362(7) . ?
C8 C14 1.382(7) . ?
C8 C37 1.388(8) . ?
C10 N3 1.376(7) . ?
C10 C31 1.389(8) . ?
C10 C60 1.448(9) . ?
C10 C29 2.032(9) . ?
N3 C25 1.415(7) . ?
C12 C14 1.378(7) . ?
C12 C26 1.396(7) . ?
C12 C18 1.494(7) . ?
C15 C19 1.395(8) . ?
O5 C29 1.199(7) . ?
C22 C30 1.504(8) . ?
C23 C28 1.386(8) . ?
C24 C30 1.347(8) . ?
C24 C25 1.396(8) . ?
C25 C36 1.323(8) . ?
C26 C39 1.385(8) . ?
C29 C31 1.477(8) . ?
C29 C60 1.496(9) . ?
C30 C40 1.332(8) . ?
C35 C36 1.336(9) . ?
C35 C40 1.410(9) . ?
C37 C39 1.353(8) . ?
O6 C60 1.188(8) . ?

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 O4 118.83(14) 4_565 2_657 ?
O1 Co1 O3 149.83(16) 4_565 . ?
O4 Co1 O3 91.34(16) 2_657 . ?
O1 Co1 N2 87.40(15) 4_565 . ?
O4 Co1 N2 88.49(15) 2_657 . ?
O3 Co1 N2 93.64(15) . . ?
O1 Co1 N1 91.11(15) 4_565 1_455 ?
O4 Co1 N1 92.37(15) 2_657 1_455 ?
O3 Co1 N1 87.57(15) . 1_455 ?
N2 Co1 N1 178.50(18) . 1_455 ?
O1 Co1 O2 90.39(15) 4_565 . ?
O4 Co1 O2 150.75(14) 2_657 . ?
O3 Co1 O2 59.44(15) . . ?
N2 Co1 O2 91.74(15) . . ?
N1 Co1 O2 88.11(15) 1_455 . ?
O1 Co1 C22 119.3(2) 4_565 . ?
O4 Co1 C22 121.9(2) 2_657 . ?
O3 Co1 C22 30.57(17) . . ?
N2 Co1 C22 94.39(17) . . ?
N1 Co1 C22 86.20(18) 1_455 . ?
O2 Co1 C22 28.93(17) . . ?
C9 N2 C15 114.9(5) . . ?
C9 N2 Co1 122.7(4) . . ?
C15 N2 Co1 122.4(4) . . ?
C7 N1 C28 116.3(5) . . ?
C7 N1 Co1 120.9(4) . 1_655 ?
C28 N1 Co1 122.8(4) . 1_655 ?
C4 C2 C19 115.4(5) . . ?
C4 C2 C1 122.7(5) . . ?
C19 C2 C1 121.9(5) . . ?
C6 C1 C23 114.2(5) . . ?
C6 C1 C2 124.0(5) . . ?
C23 C1 C2 121.7(5) . . ?
C18 O1 Co1 155.7(3) . 4_566 ?
C18 O4 Co1 129.3(4) . 2_647 ?
C22 O3 Co1 92.2(4) . . ?
C22 O2 Co1 86.5(4) . . ?
C2 C4 C9 120.6(5) . . ?
C31 N4 C8 128.7(5) . . ?
C1 C6 C7 122.4(5) . . ?
N1 C7 C6 123.4(5) . . ?
C14 C8 C37 121.3(6) . . ?
C14 C8 N4 118.1(5) . . ?
C37 C8 N4 120.7(6) . . ?
N2 C9 C4 124.6(5) . . ?
N3 C10 C31 128.8(6) . . ?
N3 C10 C60 137.3(6) . . ?
C31 C10 C60 93.9(6) . . ?
N3 C10 C29 175.4(5) . . ?
C31 C10 C29 46.6(4) . . ?
C60 C10 C29 47.3(4) . . ?
C10 N3 C25 128.1(5) . . ?
C14 C12 C26 119.0(5) . . ?
C14 C12 C18 119.7(5) . . ?
C26 C12 C18 121.3(5) . . ?
C12 C14 C8 120.3(5) . . ?
N2 C15 C19 125.8(6) . . ?
O1 C18 O4 125.1(5) . . ?
O1 C18 C12 117.5(5) . . ?
O4 C18 C12 117.5(5) . . ?
C2 C19 C15 118.4(6) . . ?
O2 C22 O3 121.6(6) . . ?
O2 C22 C30 123.1(7) . . ?
O3 C22 C30 115.3(6) . . ?
O2 C22 Co1 64.6(3) . . ?
O3 C22 Co1 57.2(3) . . ?
C30 C22 Co1 170.2(5) . . ?
C1 C23 C28 121.7(6) . . ?
C30 C24 C25 120.2(6) . . ?
C36 C25 C24 121.4(6) . . ?
C36 C25 N3 121.8(6) . . ?
C24 C25 N3 116.8(6) . . ?
C39 C26 C12 118.7(6) . . ?
N1 C28 C23 121.8(6) . . ?
O5 C29 C31 137.2(7) . . ?
O5 C29 C60 134.4(7) . . ?
C31 C29 C60 88.5(5) . . ?
O5 C29 C10 179.7(8) . . ?
C31 C29 C10 43.1(3) . . ?
C60 C29 C10 45.4(4) . . ?
C40 C30 C24 119.5(6) . . ?
C40 C30 C22 118.6(7) . . ?
C24 C30 C22 121.9(6) . . ?
N4 C31 C10 129.9(6) . . ?
N4 C31 C29 139.7(6) . . ?
C10 C31 C29 90.3(5) . . ?
C36 C35 C40 122.0(8) . . ?
C25 C36 C35 118.0(7) . . ?
C39 C37 C8 117.3(6) . . ?
C37 C39 C26 123.2(7) . . ?
C30 C40 C35 118.9(7) . . ?
O6 C60 C10 137.3(7) . . ?
O6 C60 C29 135.2(7) . . ?
C10 C60 C29 87.3(6) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.647
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.135
# 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 -0.001 -0.007 1718 545 ' '
_platon_squeeze_details          ?
