# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_rwg2021_12_395m
_database_code_depnum_ccdc_archive 'CCDC 2109477'
loop_
_audit_author_name
_audit_author_address
'Gable R.W.'
;The University of Melbourne
Australia
;
_audit_update_record             
;
2021-09-13 deposited with the CCDC.	2023-03-08 downloaded from the CCDC.
;
_audit_creation_date             2021-08-02
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
robertwg@unimelb.edu.au
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H26 Co N4 O2'
_chemical_formula_sum            'C30 H26 Co N4 O2'
_chemical_formula_weight         533.48
_chemical_melting_point          ?
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'
Co Co 0.3494 0.9721 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   19.669(4)
_cell_length_b                   7.3570(15)
_cell_length_c                   17.509(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.87(3)
_cell_angle_gamma                90
_cell_volume                     2448.8(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    610
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      27.06
_cell_measurement_theta_min      3.33
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.930
_exptl_absorpt_coefficient_mu    0.737
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6560
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'XDS (Kabsch, 2010)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1108
_exptl_crystal_recrystallization_method 
'grown by vapour diffusion of ether into methanol'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.015
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            43102
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        25.247
_diffrn_reflns_theta_max         32.074
_diffrn_reflns_theta_min         2.782
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector_area_resol_mean 13.3
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measurement_detector_type 'Dectris Eiger 16M'
_diffrn_measurement_device_type  'MX2 Beamline Australian Synchrotron'
_diffrn_measurement_method       'Omega Scan'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.71087
_diffrn_source                   'MX2 Beamline Australian Synchrotron'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3752
_reflns_number_total             3866
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_collection       'AS QEGUI'
_computing_data_reduction        'XDS (Kabsch, 2010)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         3866
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0315
_refine_ls_restrained_S_all      1.156
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0526P)²+1.1180P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.0966
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.000000 0.65783(3) 0.250000 0.02732(8) Uani 1 2 d S T P . .
O1 O 0.09298(4) 0.77684(14) 0.28431(5) 0.03540(19) Uani 1 1 d . . . . .
N1 N 0.00921(5) 0.68874(14) 0.13253(6) 0.02940(18) Uani 1 1 d . . . . .
N2 N -0.03794(5) 0.39466(15) 0.18300(6) 0.03033(18) Uani 1 1 d . . . . .
C1 C 0.13269(6) 0.85305(15) 0.24450(7) 0.0296(2) Uani 1 1 d . . . . .
C2 C 0.19556(6) 0.93950(17) 0.28790(7) 0.0330(2) Uani 1 1 d . . . . .
H2 H 0.205917 0.941636 0.343959 0.040 Uiso 1 1 calc R U . . .
C3 C 0.24164(6) 1.01987(17) 0.25111(8) 0.0361(2) Uani 1 1 d . . . . .
H3 H 0.282964 1.076594 0.282058 0.043 Uiso 1 1 calc R U . . .
C4 C 0.22858(6) 1.01942(18) 0.16854(8) 0.0380(3) Uani 1 1 d . . . . .
H4 H 0.261030 1.073229 0.143377 0.046 Uiso 1 1 calc R U . . .
C5 C 0.16768(6) 0.93927(17) 0.12459(8) 0.0343(2) Uani 1 1 d . . . . .
H5 H 0.158311 0.939684 0.068589 0.041 Uiso 1 1 calc R U . . .
C6 C 0.11865(6) 0.85629(15) 0.16049(7) 0.0297(2) Uani 1 1 d . . . . .
C7 C 0.05824(6) 0.77106(16) 0.10880(7) 0.0299(2) Uani 1 1 d . . . . .
H7 H 0.054086 0.775532 0.053567 0.036 Uiso 1 1 calc R U . . .
C8 C -0.04869(6) 0.60816(17) 0.07807(7) 0.0302(2) Uani 1 1 d . . . . .
C9 C -0.08284(6) 0.67975(18) 0.00503(7) 0.0339(2) Uani 1 1 d . . . . .
H9 H -0.064199 0.783515 -0.014767 0.041 Uiso 1 1 calc R U . . .
C10 C -0.14462(6) 0.5991(2) -0.03935(7) 0.0376(2) Uani 1 1 d . . . . .
H10 H -0.167969 0.647918 -0.089453 0.045 Uiso 1 1 calc R U . . .
C11 C -0.17202(6) 0.4478(2) -0.01038(8) 0.0387(3) Uani 1 1 d . . . . .
H11 H -0.214537 0.394708 -0.040412 0.046 Uiso 1 1 calc R U . . .
C12 C -0.13761(6) 0.37310(19) 0.06239(8) 0.0358(2) Uani 1 1 d . . . . .
H12 H -0.156112 0.268434 0.081675 0.043 Uiso 1 1 calc R U . . .
C13 C -0.07604(6) 0.45300(16) 0.10650(7) 0.0310(2) Uani 1 1 d . . . . .
C14 C -0.07561(6) 0.29346(19) 0.23126(7) 0.0359(2) Uani 1 1 d . . . . .
H14A H -0.084269 0.166968 0.211923 0.043 Uiso 1 1 calc R U . . .
H14B H -0.121410 0.351771 0.229172 0.043 Uiso 1 1 calc R U . . .
C15 C 0.02805(6) 0.29579(18) 0.18328(7) 0.0343(2) Uani 1 1 d . . . . .
H15A H 0.052636 0.357212 0.147721 0.041 Uiso 1 1 calc R U . . .
H15B H 0.017040 0.169838 0.164191 0.041 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 1.9769(9) . ?
Co1 O1 1.9769(9) 2 ?
Co1 N1 2.1228(11) 2 ?
Co1 N1 2.1228(11) . ?
Co1 N2 2.2874(11) . ?
Co1 N2 2.2874(11) 2 ?
O1 C1 1.2998(14) . ?
N1 C7 1.2942(15) . ?
N1 C8 1.4143(15) . ?
N2 C13 1.4229(15) . ?
N2 C14 1.4623(16) . ?
N2 C15 1.4870(15) . ?
C1 C2 1.4243(16) . ?
C1 C6 1.4254(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.3732(17) . ?
C3 H3 0.9500 . ?
C3 C4 1.402(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.3789(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.4175(16) . ?
C6 C7 1.4395(16) . ?
C7 H7 0.9500 . ?
C8 C9 1.3867(16) . ?
C8 C13 1.4063(17) . ?
C9 H9 0.9500 . ?
C9 C10 1.3954(17) . ?
C10 H10 0.9500 . ?
C10 C11 1.389(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.3929(19) . ?
C12 H12 0.9500 . ?
C12 C13 1.3887(16) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5478(18) 2 ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?

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 O1 127.42(6) . 2 ?
O1 Co1 N1 86.82(5) . . ?
O1 Co1 N1 87.74(4) . 2 ?
O1 Co1 N1 87.74(4) 2 . ?
O1 Co1 N1 86.82(4) 2 2 ?
O1 Co1 N2 93.69(4) 2 . ?
O1 Co1 N2 133.26(4) 2 2 ?
O1 Co1 N2 93.69(4) . 2 ?
O1 Co1 N2 133.26(4) . . ?
N1 Co1 N1 167.70(6) 2 . ?
N1 Co1 N2 72.03(4) 2 2 ?
N1 Co1 N2 72.03(4) . . ?
N1 Co1 N2 119.33(4) . 2 ?
N1 Co1 N2 119.33(4) 2 . ?
N2 Co1 N2 64.35(5) . 2 ?
C1 O1 Co1 131.64(8) . . ?
C7 N1 Co1 128.10(8) . . ?
C7 N1 C8 121.14(10) . . ?
C8 N1 Co1 110.74(8) . . ?
C13 N2 Co1 104.54(8) . . ?
C13 N2 C14 118.36(9) . . ?
C13 N2 C15 113.52(10) . . ?
C14 N2 Co1 106.36(8) . . ?
C14 N2 C15 108.68(10) . . ?
C15 N2 Co1 104.05(7) . . ?
O1 C1 C2 117.73(11) . . ?
O1 C1 C6 125.22(10) . . ?
C2 C1 C6 117.05(11) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 C1 121.95(12) . . ?
C3 C2 H2 119.0 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 120.97(11) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.65(12) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 H5 119.0 . . ?
C4 C5 C6 121.94(12) . . ?
C6 C5 H5 119.0 . . ?
C1 C6 C7 123.47(11) . . ?
C5 C6 C1 119.43(11) . . ?
C5 C6 C7 117.03(11) . . ?
N1 C7 C6 124.39(11) . . ?
N1 C7 H7 117.8 . . ?
C6 C7 H7 117.8 . . ?
C9 C8 N1 125.32(11) . . ?
C9 C8 C13 119.73(11) . . ?
C13 C8 N1 114.62(10) . . ?
C8 C9 H9 120.1 . . ?
C8 C9 C10 119.90(12) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.10(12) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.49(11) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.43(12) . . ?
C13 C12 H12 120.3 . . ?
C8 C13 N2 114.91(10) . . ?
C12 C13 N2 124.70(11) . . ?
C12 C13 C8 120.33(11) . . ?
N2 C14 H14A 110.4 . . ?
N2 C14 H14B 110.4 . . ?
N2 C14 C15 106.44(9) . 2 ?
H14A C14 H14B 108.6 . . ?
C15 C14 H14A 110.4 2 . ?
C15 C14 H14B 110.4 2 . ?
N2 C15 C14 108.60(10) . 2 ?
N2 C15 H15A 110.0 . . ?
N2 C15 H15B 110.0 . . ?
C14 C15 H15A 110.0 2 . ?
C14 C15 H15B 110.0 2 . ?
H15A C15 H15B 108.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Co1 O1 C1 C2 175.48(8) . . . . ?
Co1 O1 C1 C6 -4.95(18) . . . . ?
Co1 N1 C7 C6 1.56(17) . . . . ?
Co1 N1 C8 C9 140.39(10) . . . . ?
Co1 N1 C8 C13 -33.00(12) . . . . ?
Co1 N2 C13 C8 35.43(11) . . . . ?
Co1 N2 C13 C12 -141.60(11) . . . . ?
Co1 N2 C14 C15 -47.52(11) . . . 2 ?
Co1 N2 C15 C14 49.22(11) . . . 2 ?
O1 C1 C2 C3 178.43(11) . . . . ?
O1 C1 C6 C5 -177.94(11) . . . . ?
O1 C1 C6 C7 -1.15(18) . . . . ?
N1 C8 C9 C10 -172.19(12) . . . . ?
N1 C8 C13 N2 -4.43(15) . . . . ?
N1 C8 C13 C12 172.75(11) . . . . ?
C1 C2 C3 C4 -0.22(19) . . . . ?
C1 C6 C7 N1 2.63(18) . . . . ?
C2 C1 C6 C5 1.64(16) . . . . ?
C2 C1 C6 C7 178.43(11) . . . . ?
C2 C3 C4 C5 1.2(2) . . . . ?
C3 C4 C5 C6 -0.7(2) . . . . ?
C4 C5 C6 C1 -0.76(18) . . . . ?
C4 C5 C6 C7 -177.76(11) . . . . ?
C5 C6 C7 N1 179.49(11) . . . . ?
C6 C1 C2 C3 -1.18(17) . . . . ?
C7 N1 C8 C9 -38.27(18) . . . . ?
C7 N1 C8 C13 148.34(11) . . . . ?
C8 N1 C7 C6 179.96(11) . . . . ?
C8 C9 C10 C11 0.2(2) . . . . ?
C9 C8 C13 N2 -178.22(11) . . . . ?
C9 C8 C13 C12 -1.04(18) . . . . ?
C9 C10 C11 C12 -1.1(2) . . . . ?
C10 C11 C12 C13 1.0(2) . . . . ?
C11 C12 C13 N2 177.00(12) . . . . ?
C11 C12 C13 C8 0.12(19) . . . . ?
C13 N2 C14 C15 -164.64(10) . . . 2 ?
C13 N2 C15 C14 162.25(10) . . . 2 ?
C13 C8 C9 C10 0.89(18) . . . . ?
C14 N2 C13 C8 153.51(11) . . . . ?
C14 N2 C13 C12 -23.52(18) . . . . ?
C14 N2 C15 C14 -63.80(11) . . . 2 ?
C15 N2 C13 C8 -77.30(13) . . . . ?
C15 N2 C13 C12 105.67(14) . . . . ?
C15 N2 C14 C15 63.96(12) . . . 2 ?

_olex2_exptl_crystal_mounting_method mounted
_olex2_submission_special_instructions 'No special instructions were received'
