# Supplementary Information (SI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_test_pl_sq
_audit_block_doi                 10.5517/ccdc.csd.cc2jfywt
_database_code_depnum_ccdc_archive 'CCDC 2337117'
_audit_update_record             
;
2024-03-03 deposited with the CCDC.	2024-11-12 downloaded from the CCDC.
;
_audit_creation_date             2024-03-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
dingwyzzz@163.com
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C44 H26 Co3 N4 O13, 4[C3H7NO], 5[CH4O]'
_chemical_formula_sum            'C61 H73.97 Co3 N8 O22'
_chemical_formula_weight         1448.04
_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      hexagonal
_space_group_IT_number           194
_space_group_name_H-M_alt        'P 63/m m c'
_space_group_name_Hall           '-P 6c 2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x-y, x, z+1/2'
'-y, x-y, z'
'-x, -y, z+1/2'
'-x+y, -x, z'
'y, -x+y, z+1/2'
'-y, -x, -z+1/2'
'x-y, -y, -z'
'x, x-y, -z+1/2'
'y, x, -z'
'-x+y, y, -z+1/2'
'-x, -x+y, -z'
'-x, -y, -z'
'-x+y, -x, -z-1/2'
'y, -x+y, -z'
'x, y, -z-1/2'
'x-y, x, -z'
'-y, x-y, -z-1/2'
'y, x, z-1/2'
'-x+y, y, z'
'-x, -x+y, z-1/2'
'-y, -x, z'
'x-y, -y, z-1/2'
'x, x-y, z'

_cell_length_a                   17.0841(8)
_cell_length_b                   17.0841(8)
_cell_length_c                   14.9800(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3786.4(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2891
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      22.17
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.721
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6507
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0685 before and 0.0615 after correction.
The Ratio of minimum to maximum transmission is 0.8726.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1506
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0977
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            26348
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.391
_diffrn_reflns_theta_min         2.384
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1423
_reflns_number_total             1803
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     65
_refine_ls_number_reflns         1803
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.023
_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)+(0.0604P)²+0.9342P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1062
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Shared sites
{C1, N2}
3. Uiso/Uaniso restraints and constraints
Uanis(C1) = Uanis(N2)
4. Others
 Fixed Sof: C1(0.16665) H1(0.16665) N2(0.083333)
5.a Riding coordinates:
 C8(H8)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 -0.26463(2) 0.47074(3) -0.250000 0.02125(15) Uani 1 4 d S T P . .
O1 O -0.333333 0.333333 -0.250000 0.0116(6) Uani 1 12 d S T P . .
O2 O -0.34765(11) 0.47668(10) -0.34739(12) 0.0574(5) Uani 1 1 d . . . . .
N1 N -0.19154(10) 0.6169(2) -0.250000 0.0359(7) Uani 1 4 d S T P . .
C6 C -0.42636(9) 0.42636(9) -0.37177(18) 0.0354(6) Uani 1 2 d S T P . .
C7 C -0.46467(10) 0.46467(10) -0.43803(19) 0.0403(7) Uani 1 2 d S T P . .
C3 C -0.09653(13) 0.8069(3) -0.250000 0.0435(10) Uani 1 4 d S T P . .
C1 C 0.04624(12) 0.95376(12) -0.250000 0.0488(11) Uani 0.6666 4 d S T P . .
H1 H 0.077666 0.922334 -0.250000 0.059 Uiso 0.6666 4 calc R U P . .
C2 C -0.04618(13) 0.9076(3) -0.250000 0.0440(10) Uani 1 4 d S T P . .
C8 C -0.41337(17) 0.55141(17) -0.4698(2) 0.0767(10) Uani 1 1 d . . . . .
H8 H -0.355324 0.587911 -0.447582 0.092 Uiso 1 1 d R U . . .
C5 C -0.2335(2) 0.6646(2) -0.250000 0.0747(13) Uani 1 2 d S T P . .
H5 H -0.296406 0.633318 -0.250000 0.090 Uiso 1 2 calc R U P . .
C4 C -0.1891(2) 0.7587(2) -0.250000 0.0849(16) Uani 1 2 d S T P . .
H4 H -0.221996 0.788572 -0.250000 0.102 Uiso 1 2 calc R U P . .
N2 N 0.04624(12) 0.95376(12) -0.250000 0.0488(11) Uani 0.3333 4 d S T P . .


_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 2.0330(4) . ?
Co1 O2 2.0722(13) . ?
Co1 O2 2.0722(13) 16 ?
Co1 O2 2.0723(13) 20_455 ?
Co1 O2 2.0723(13) 11_454 ?
Co1 N1 2.163(3) . ?
O2 C6 1.2347(18) . ?
N1 C5 1.328(4) 20_455 ?
N1 C5 1.328(4) . ?
C6 C7 1.507(3) . ?
C7 C8 1.375(3) 22 ?
C7 C8 1.375(3) . ?
C3 C2 1.490(5) . ?
C3 C4 1.369(4) 20_455 ?
C3 C4 1.369(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.367(3) 3_675 ?
C1 C2 1.367(3) . ?
C8 C8 1.381(4) 10_464 ?
C8 H8 0.9298 . ?
C5 H5 0.9300 . ?
C5 C4 1.393(4) . ?
C4 H4 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
O1 Co1 O2 92.43(4) . 16 ?
O1 Co1 O2 92.43(4) . 20_455 ?
O1 Co1 O2 92.43(4) . . ?
O1 Co1 O2 92.43(4) . 11_454 ?
O1 Co1 N1 180.0 . . ?
O2 Co1 O2 175.14(8) . 11_454 ?
O2 Co1 O2 175.14(8) 16 20_455 ?
O2 Co1 O2 89.50(11) 16 . ?
O2 Co1 O2 90.30(11) 16 11_454 ?
O2 Co1 O2 90.30(11) . 20_455 ?
O2 Co1 O2 89.50(11) 11_454 20_455 ?
O2 Co1 N1 87.57(4) . . ?
O2 Co1 N1 87.57(4) 11_454 . ?
O2 Co1 N1 87.57(4) 16 . ?
O2 Co1 N1 87.57(4) 20_455 . ?
Co1 O1 Co1 120.0 14_455 . ?
Co1 O1 Co1 120.0 14_455 3_565 ?
Co1 O1 Co1 120.0 . 3_565 ?
C6 O2 Co1 135.06(14) . . ?
C5 N1 Co1 122.09(18) 20_455 . ?
C5 N1 Co1 122.09(18) . . ?
C5 N1 C5 115.8(4) 20_455 . ?
O2 C6 O2 126.4(2) . 22 ?
O2 C6 C7 116.79(12) . . ?
O2 C6 C7 116.79(12) 22 . ?
C8 C7 C6 120.98(13) . . ?
C8 C7 C6 120.98(13) 22 . ?
C8 C7 C8 118.0(3) 22 . ?
C4 C3 C2 121.43(19) 20_455 . ?
C4 C3 C2 121.43(19) . . ?
C4 C3 C4 117.1(4) 20_455 . ?
C2 C1 H1 120.1 3_675 . ?
C2 C1 H1 120.1 . . ?
C2 C1 C2 119.9(4) . 3_675 ?
C1 C2 C3 119.9(2) . . ?
C1 C2 C3 119.9(2) 14_465 . ?
C1 C2 C1 120.1(4) . 14_465 ?
C7 C8 C8 120.97(13) . 10_464 ?
C7 C8 H8 119.4 . . ?
C8 C8 H8 119.6 10_464 . ?
N1 C5 H5 118.1 . . ?
N1 C5 C4 123.9(3) . . ?
C4 C5 H5 118.1 . . ?
C3 C4 C5 119.6(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?

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 O2 C6 O2 -9.3(5) . . . 22 ?
Co1 O2 C6 C7 170.89(19) . . . . ?
Co1 N1 C5 C4 180.0 . . . . ?
O2 C6 C7 C8 -0.5(4) 22 . . 22 ?
O2 C6 C7 C8 -179.3(3) 22 . . . ?
O2 C6 C7 C8 179.3(3) . . . 22 ?
O2 C6 C7 C8 0.5(4) . . . . ?
N1 C5 C4 C3 0.0 . . . . ?
C6 C7 C8 C8 -179.8(4) . . . 10_464 ?
C2 C3 C4 C5 180.0 . . . . ?
C2 C1 C2 C3 180.0 3_675 . . . ?
C2 C1 C2 C1 0.0 3_675 . . 14_465 ?
C8 C7 C8 C8 1.4(7) 22 . . 10_464 ?
C5 N1 C5 C4 0.0 20_455 . . . ?
C4 C3 C2 C1 180.0 . . . . ?
C4 C3 C2 C1 180.0 20_455 . . 14_465 ?
C4 C3 C2 C1 0.0 20_455 . . . ?
C4 C3 C2 C1 0.0 . . . 14_465 ?
C4 C3 C4 C5 0.0 20_455 . . . ?

_platon_squeeze_details          ?
_platon_squeeze_special_details  
;
A solvent mask was calculated and 469 electrons were 
found in a volume of 2203Å³ in 1 void per unit cell. 
This is consistent with the presence of 
4[C3H7NO], 5[CH4O] per Asymmetric Unit 
which account for 500 electrons 
per unit cell.
;
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 -0.016 -0.012 -0.004 2203 469 '8 C3H7NO,9.984 CH4O'

_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'
