# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_1p
_database_code_depnum_ccdc_archive 'CCDC 1527492'
_audit_update_record             
;
2017-01-14 deposited with the CCDC.
2017-06-02 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            'C28 H18 Co N4 O4'
_chemical_formula_weight         533.39

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'

_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                   17.7907(17)
_cell_length_b                   15.7390(12)
_cell_length_c                   14.5480(12)
_cell_angle_alpha                90
_cell_angle_beta                 125.091(9)
_cell_angle_gamma                90
_cell_volume                     3333.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2525
_cell_measurement_theta_min      3.1290
_cell_measurement_theta_max      27.7420

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.063
_exptl_crystal_F_000             1092
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.546
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.84963
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8095
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.921
_diffrn_reflns_theta_max         28.875
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.861
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.861
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3778
_reflns_number_gt                2756
_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.
;
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 0.500 0.000 0.073 647 127 ' '
2 0.000 0.500 -0.021 647 127 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0695P)²] 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         3778
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1317
_refine_ls_wR_factor_gt          0.1233
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_restrained_S_all      0.977
_refine_ls_shift/su_max          0.001
_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
O2 O 0.85834(10) 0.16431(11) 0.65719(13) 0.0517(4) Uani 1 1 d . . . . .
O1 O 0.95253(11) 0.23676(10) 0.81104(14) 0.0539(4) Uani 1 1 d . . . . .
C14 C 0.87322(14) 0.22283(14) 0.72532(19) 0.0425(5) Uani 1 1 d . . . . .
C11 C 0.79414(15) 0.27670(14) 0.70218(19) 0.0456(5) Uani 1 1 d . . . . .
C10 C 0.70986(15) 0.27097(16) 0.59961(19) 0.0510(6) Uani 1 1 d . . . . .
H10 H 0.7020 0.2331 0.5457 0.061 Uiso 1 1 calc R U . . .
C12 C 0.80527(17) 0.33298(16) 0.7819(2) 0.0540(6) Uani 1 1 d . . . . .
H12 H 0.8624 0.3382 0.8501 0.065 Uiso 1 1 calc R U . . .
Co1 Co 0.5000 0.63711(2) 0.7500 0.04057(17) Uani 1 2 d S T P . .
N1 N 0.50608(12) 0.54028(12) 0.65387(16) 0.0449(4) Uani 1 1 d . . . . .
N2 N 0.57425(12) 0.42809(12) 0.63716(15) 0.0467(5) Uani 1 1 d . . . . .
C8 C 0.64911(15) 0.37613(14) 0.65843(19) 0.0450(5) Uani 1 1 d . . . . .
C13 C 0.73273(17) 0.38146(16) 0.7614(2) 0.0542(6) Uani 1 1 d . . . . .
H13 H 0.7400 0.4175 0.8167 0.065 Uiso 1 1 calc R U . . .
C1 C 0.58332(15) 0.50816(14) 0.67782(19) 0.0464(5) Uani 1 1 d . . . . .
H1 H 0.6389 0.5372 0.7186 0.056 Uiso 1 1 calc R U . . .
C2 C 0.44082(15) 0.47725(14) 0.59346(19) 0.0456(5) Uani 1 1 d . . . . .
C7 C 0.48184(16) 0.40636(15) 0.5821(2) 0.0520(6) Uani 1 1 d . . . . .
C6 C 0.4325(2) 0.3336(2) 0.5273(3) 0.0824(10) Uani 1 1 d . . . . .
H6 H 0.4603 0.2862 0.5205 0.099 Uiso 1 1 calc R U . . .
C3 C 0.34778(17) 0.47717(18) 0.5488(2) 0.0662(7) Uani 1 1 d . . . . .
H3 H 0.3195 0.5241 0.5555 0.079 Uiso 1 1 calc R U . . .
C4 C 0.2993(2) 0.4047(2) 0.4944(3) 0.0975(12) Uani 1 1 d . . . . .
H4 H 0.2369 0.4026 0.4641 0.117 Uiso 1 1 calc R U . . .
C5 C 0.3404(2) 0.3349(2) 0.4832(3) 0.1127(15) Uani 1 1 d . . . . .
H5 H 0.3048 0.2874 0.4449 0.135 Uiso 1 1 calc R U . . .
C9 C 0.63690(15) 0.32132(16) 0.5764(2) 0.0540(6) Uani 1 1 d . . . . .
H9 H 0.5806 0.3183 0.5068 0.065 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
O2 C14 1.265(3) . ?
O2 Co1 2.1085(15) 3_545 ?
O1 C14 1.253(3) . ?
O1 Co1 2.1964(15) 3_545 ?
C14 C11 1.506(3) . ?
C14 Co1 2.471(2) 3_545 ?
C11 C12 1.380(3) . ?
C11 C10 1.382(3) . ?
C10 C9 1.387(3) . ?
C12 C13 1.377(3) . ?
Co1 O2 2.1084(15) 4_656 ?
Co1 O2 2.1084(15) 3_455 ?
Co1 N1 2.1128(18) . ?
Co1 N1 2.1129(18) 2_656 ?
Co1 O1 2.1964(15) 3_455 ?
Co1 O1 2.1964(16) 4_656 ?
Co1 C14 2.471(2) 4_656 ?
Co1 C14 2.471(2) 3_455 ?
N1 C1 1.309(3) . ?
N1 C2 1.390(3) . ?
N2 C1 1.362(3) . ?
N2 C7 1.396(3) . ?
N2 C8 1.437(3) . ?
C8 C9 1.384(3) . ?
C8 C13 1.379(3) . ?
C2 C3 1.388(3) . ?
C2 C7 1.394(3) . ?
C7 C6 1.383(4) . ?
C6 C5 1.375(4) . ?
C3 C4 1.374(4) . ?
C4 C5 1.379(4) . ?

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
C14 O2 Co1 90.66(13) . 3_545 ?
C14 O1 Co1 86.99(13) . 3_545 ?
O1 C14 O2 121.1(2) . . ?
O1 C14 C11 119.8(2) . . ?
O2 C14 C11 119.2(2) . . ?
O1 C14 Co1 62.58(11) . 3_545 ?
O2 C14 Co1 58.57(11) . 3_545 ?
C11 C14 Co1 175.97(16) . 3_545 ?
C12 C11 C10 119.4(2) . . ?
C12 C11 C14 120.6(2) . . ?
C10 C11 C14 119.9(2) . . ?
C9 C10 C11 120.5(2) . . ?
C13 C12 C11 120.7(2) . . ?
O2 Co1 O2 156.57(10) 4_656 3_455 ?
O2 Co1 N1 94.19(7) 4_656 . ?
O2 Co1 N1 102.70(7) 3_455 . ?
O2 Co1 N1 102.70(7) 4_656 2_656 ?
O2 Co1 N1 94.19(7) 3_455 2_656 ?
N1 Co1 N1 87.68(10) . 2_656 ?
O2 Co1 O1 101.06(6) 4_656 3_455 ?
O2 Co1 O1 61.19(6) 3_455 3_455 ?
N1 Co1 O1 163.87(7) . 3_455 ?
N1 Co1 O1 93.99(7) 2_656 3_455 ?
O2 Co1 O1 61.19(6) 4_656 4_656 ?
O2 Co1 O1 101.06(6) 3_455 4_656 ?
N1 Co1 O1 93.99(7) . 4_656 ?
N1 Co1 O1 163.87(7) 2_656 4_656 ?
O1 Co1 O1 88.86(9) 3_455 4_656 ?
O2 Co1 C14 30.78(6) 4_656 4_656 ?
O2 Co1 C14 129.59(7) 3_455 4_656 ?
N1 Co1 C14 95.76(7) . 4_656 ?
N1 Co1 C14 133.43(7) 2_656 4_656 ?
O1 Co1 C14 94.72(6) 3_455 4_656 ?
O1 Co1 C14 30.44(6) 4_656 4_656 ?
O2 Co1 C14 129.59(7) 4_656 3_455 ?
O2 Co1 C14 30.78(6) 3_455 3_455 ?
N1 Co1 C14 133.43(7) . 3_455 ?
N1 Co1 C14 95.75(7) 2_656 3_455 ?
O1 Co1 C14 30.44(6) 3_455 3_455 ?
O1 Co1 C14 94.72(6) 4_656 3_455 ?
C14 Co1 C14 113.80(10) 4_656 3_455 ?
C1 N1 C2 105.07(18) . . ?
C1 N1 Co1 123.20(16) . . ?
C2 N1 Co1 126.26(13) . . ?
C1 N2 C7 106.40(18) . . ?
C1 N2 C8 124.72(19) . . ?
C7 N2 C8 128.6(2) . . ?
C9 C8 C13 120.7(2) . . ?
C9 C8 N2 120.1(2) . . ?
C13 C8 N2 119.12(19) . . ?
C12 C13 C8 119.5(2) . . ?
N1 C1 N2 113.4(2) . . ?
N1 C2 C3 129.4(2) . . ?
N1 C2 C7 110.02(19) . . ?
C3 C2 C7 120.6(2) . . ?
C6 C7 C2 122.0(2) . . ?
C6 C7 N2 132.9(2) . . ?
C2 C7 N2 105.1(2) . . ?
C5 C6 C7 116.5(3) . . ?
C4 C3 C2 117.1(2) . . ?
C5 C4 C3 122.0(3) . . ?
C6 C5 C4 121.9(3) . . ?
C8 C9 C10 119.0(2) . . ?

_refine_diff_density_max         0.355
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.052

