# Electronic Supplementary Material (ESI) for Energy 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2285196'
loop_
_audit_author_name
_audit_author_address
'Shaikh M. Mobin'
;IIT INDORE
India
;
_audit_update_record             
;
2023-07-28 deposited with the CCDC.	2023-10-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H13.50 Co0.50 N1.50 O3.50'
_chemical_formula_weight         228.18

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           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'

_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+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   10.3390(4)
_cell_length_b                   7.1811(3)
_cell_length_c                   13.8946(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.287(3)
_cell_angle_gamma                90
_cell_volume                     1031.35(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3804
_cell_measurement_theta_min      3.4270
_cell_measurement_theta_max      27.8940

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_F_000             478
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.877
_shelx_estimated_absorpt_T_min   0.761
_shelx_estimated_absorpt_T_max   0.837
_exptl_absorpt_correction_T_min  0.71696
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.393
_oxdiff_exptl_absorpt_empirical_full_max 2.385
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_reflns_number            10592
_diffrn_reflns_av_unetI/netI     0.0606
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.933
_diffrn_reflns_theta_max         29.058
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.915
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2712
_reflns_number_gt                2123
_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       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Diamond
_computing_publication_material  Shelx97
_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)+(0.0542P)²+1.2760P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2712
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1432
_refine_ls_wR_factor_gt          0.1288
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.000
_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
Co1 Co 0.76818(5) 0.750000 0.83635(4) 0.02135(19) Uani 1 2 d S T P . .
O1 O 0.5848(3) 0.750000 0.7771(2) 0.0261(6) Uani 1 2 d S T P . .
O2 O 0.4610(3) 0.750000 0.9072(2) 0.0378(8) Uani 1 2 d S T P . .
O4 O -0.0228(3) 0.750000 0.8640(2) 0.0301(7) Uani 1 2 d S T P . .
O5 O -0.1063(3) 0.750000 0.7172(2) 0.0292(7) Uani 1 2 d S T P . .
O6 O 0.2669(4) 0.750000 0.4960(3) 0.0694(16) Uani 1 2 d S T P . .
N1 N 0.7670(2) 0.4336(3) 0.83570(17) 0.0226(5) Uani 1 1 d . . . . .
C1 C 0.4760(4) 0.750000 0.8188(3) 0.0246(9) Uani 1 2 d S T P . .
C2 C -0.0085(4) 0.750000 0.7743(3) 0.0245(9) Uani 1 2 d S T P . .
C3 C 0.3577(4) 0.750000 0.7535(3) 0.0248(9) Uani 1 2 d S T P . .
C4 C 0.2331(4) 0.750000 0.7936(3) 0.0232(8) Uani 1 2 d S T P . .
H4 H 0.224009 0.750000 0.859993 0.028 Uiso 1 2 calc R U P . .
C5 C 0.1248(4) 0.750000 0.7332(3) 0.0244(8) Uani 1 2 d S T P . .
C6 C 0.1381(4) 0.750000 0.6337(3) 0.0357(11) Uani 1 2 d S T P . .
H6 H 0.064894 0.750000 0.593502 0.043 Uiso 1 2 calc R U P . .
C7 C 0.2608(5) 0.750000 0.5942(3) 0.0397(12) Uani 1 2 d S T P . .
C8 C 0.3694(4) 0.750000 0.6543(3) 0.0326(10) Uani 1 2 d S T P . .
H8 H 0.451207 0.750000 0.627862 0.039 Uiso 1 2 calc R U P . .
C9 C 0.6445(4) 0.3563(5) 0.8712(4) 0.0758(18) Uani 1 1 d . . . . .
H9A H 0.573218 0.400667 0.830837 0.091 Uiso 1 1 calc R U . . .
H9B H 0.631058 0.400661 0.936164 0.091 Uiso 1 1 calc R U . . .
C10 C 0.8707(5) 0.3558(5) 0.8967(4) 0.0672(15) Uani 1 1 d . . . . .
H10A H 0.860978 0.400023 0.962110 0.081 Uiso 1 1 calc R U . . .
H10B H 0.953356 0.400019 0.874144 0.081 Uiso 1 1 calc R U . . .
C11 C 0.7814(6) 0.3568(5) 0.7386(3) 0.0636(14) Uani 1 1 d . . . . .
H11A H 0.861815 0.401224 0.712265 0.076 Uiso 1 1 calc R U . . .
H11B H 0.710985 0.401226 0.697375 0.076 Uiso 1 1 calc R U . . .
C111 C 0.7357(6) 0.750000 1.0708(4) 0.0539(15) Uani 1 2 d S T P . .
H00A H 0.662065 0.750000 1.111629 0.081 Uiso 1 2 calc R U P . .
H00B H 0.786933 0.640847 1.083409 0.081 Uiso 0.5 1 calc R U P . .
H00C H 0.786933 0.859153 1.083409 0.081 Uiso 0.5 1 calc R U P . .
O111 O 0.6938(3) 0.750000 0.9744(2) 0.0348(7) Uani 1 2 d S T P . .
N111 N 0.7234(4) 0.750000 0.4186(3) 0.0462(11) Uani 1 2 d S T P . .
C222 C 0.8477(7) 0.750000 0.4695(6) 0.085(2) Uani 1 2 d S T P . .
H11C H 0.915938 0.750000 0.423848 0.127 Uiso 1 2 calc R U P . .
H11D H 0.854569 0.859153 0.509212 0.127 Uiso 0.5 1 calc R U P . .
H11E H 0.854569 0.640847 0.509212 0.127 Uiso 0.5 1 calc R U P . .
C333 C 0.7221(7) 0.750000 0.3160(4) 0.0616(17) Uani 1 2 d S T P . .
H22A H 0.809377 0.750000 0.293855 0.092 Uiso 1 2 calc R U P . .
H22B H 0.678037 0.640847 0.292573 0.092 Uiso 0.5 1 calc R U P . .
H22C H 0.678037 0.859153 0.292573 0.092 Uiso 0.5 1 calc R U P . .
C444 C 0.6133(8) 0.750000 0.4644(5) 0.086(3) Uani 1 2 d S T P . .
H444 H 0.617828 0.750000 0.531290 0.103 Uiso 1 2 calc R U P . .
O222 O 0.5051(5) 0.750000 0.4260(4) 0.0946(19) Uani 1 2 d S T P . .
H101 H 0.603(7) 0.750000 0.963(5) 0.08(2) Uiso 1 2 d S . P . .
H6A H 0.331(7) 0.750000 0.476(5) 0.06(2) Uiso 1 2 d S . 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 2.050(3) . ?
Co1 O111 2.083(3) . ?
Co1 O5 2.126(3) 1_655 ?
Co1 O4 2.186(3) 1_655 ?
Co1 N1 2.272(2) . ?
Co1 N1 2.272(2) 4_575 ?
Co1 C2 2.482(4) 1_655 ?
O1 C1 1.277(5) . ?
O2 C1 1.241(5) . ?
O4 C2 1.258(5) . ?
O5 C2 1.271(5) . ?
O6 C7 1.367(6) . ?
O6 H6A 0.72(7) . ?
N1 C10 1.463(4) . ?
N1 C11 1.468(4) . ?
N1 C9 1.478(4) . ?
C1 C3 1.506(6) . ?
C2 C5 1.504(5) . ?
C3 C8 1.386(6) . ?
C3 C4 1.415(5) . ?
C4 C5 1.384(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(6) . ?
C6 C7 1.394(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.385(6) . ?
C8 H8 0.9300 . ?
C9 C9 1.526(7) 4_565 ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C10 1.519(7) 4_565 ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C11 1.534(7) 4_565 ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C111 O111 1.398(6) . ?
C111 H00A 0.9600 . ?
C111 H00B 0.9600 . ?
C111 H00C 0.9600 . ?
O111 H101 0.95(7) . ?
N111 C444 1.316(8) . ?
N111 C333 1.425(7) . ?
N111 C222 1.453(8) . ?
C222 H11C 0.9600 . ?
C222 H11D 0.9600 . ?
C222 H11E 0.9600 . ?
C333 H22A 0.9600 . ?
C333 H22B 0.9600 . ?
C333 H22C 0.9600 . ?
C444 O222 1.228(9) . ?
C444 H444 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 O111 90.71(13) . . ?
O1 Co1 O5 105.21(11) . 1_655 ?
O111 Co1 O5 164.08(12) . 1_655 ?
O1 Co1 O4 166.45(12) . 1_655 ?
O111 Co1 O4 102.84(12) . 1_655 ?
O5 Co1 O4 61.24(11) 1_655 1_655 ?
O1 Co1 N1 89.62(6) . . ?
O111 Co1 N1 90.09(6) . . ?
O5 Co1 N1 90.02(6) 1_655 . ?
O4 Co1 N1 90.35(6) 1_655 . ?
O1 Co1 N1 89.62(6) . 4_575 ?
O111 Co1 N1 90.09(6) . 4_575 ?
O5 Co1 N1 90.02(6) 1_655 4_575 ?
O4 Co1 N1 90.35(6) 1_655 4_575 ?
N1 Co1 N1 179.23(13) . 4_575 ?
O1 Co1 C2 136.02(13) . 1_655 ?
O111 Co1 C2 133.27(14) . 1_655 ?
O5 Co1 C2 30.81(13) 1_655 1_655 ?
O4 Co1 C2 30.43(13) 1_655 1_655 ?
N1 Co1 C2 90.21(6) . 1_655 ?
N1 Co1 C2 90.21(6) 4_575 1_655 ?
C1 O1 Co1 129.4(3) . . ?
C2 O4 Co1 87.9(2) . 1_455 ?
C2 O5 Co1 90.3(2) . 1_455 ?
C7 O6 H6A 117(6) . . ?
C10 N1 C11 107.5(3) . . ?
C10 N1 C9 106.6(3) . . ?
C11 N1 C9 105.7(3) . . ?
C10 N1 Co1 112.06(19) . . ?
C11 N1 Co1 112.24(19) . . ?
C9 N1 Co1 112.28(18) . . ?
O2 C1 O1 125.4(4) . . ?
O2 C1 C3 118.6(4) . . ?
O1 C1 C3 116.0(4) . . ?
O4 C2 O5 120.6(4) . . ?
O4 C2 C5 120.4(4) . . ?
O5 C2 C5 119.1(4) . . ?
O4 C2 Co1 61.7(2) . 1_455 ?
O5 C2 Co1 58.9(2) . 1_455 ?
C5 C2 Co1 178.0(3) . 1_455 ?
C8 C3 C4 119.4(4) . . ?
C8 C3 C1 120.7(4) . . ?
C4 C3 C1 119.8(4) . . ?
C5 C4 C3 119.6(4) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.4(4) . . ?
C4 C5 C2 120.4(4) . . ?
C6 C5 C2 119.3(4) . . ?
C5 C6 C7 120.1(4) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
O6 C7 C8 123.2(4) . . ?
O6 C7 C6 117.1(4) . . ?
C8 C7 C6 119.7(4) . . ?
C7 C8 C3 120.8(4) . . ?
C7 C8 H8 119.6 . . ?
C3 C8 H8 119.6 . . ?
N1 C9 C9 112.07(16) . 4_565 ?
N1 C9 H9A 109.2 . . ?
C9 C9 H9A 109.2 4_565 . ?
N1 C9 H9B 109.2 . . ?
C9 C9 H9B 109.2 4_565 . ?
H9A C9 H9B 107.9 . . ?
N1 C10 C10 112.44(16) . 4_565 ?
N1 C10 H10A 109.1 . . ?
C10 C10 H10A 109.1 4_565 . ?
N1 C10 H10B 109.1 . . ?
C10 C10 H10B 109.1 4_565 . ?
H10A C10 H10B 107.8 . . ?
N1 C11 C11 112.06(16) . 4_565 ?
N1 C11 H11A 109.2 . . ?
C11 C11 H11A 109.2 4_565 . ?
N1 C11 H11B 109.2 . . ?
C11 C11 H11B 109.2 4_565 . ?
H11A C11 H11B 107.9 . . ?
O111 C111 H00A 109.5 . . ?
O111 C111 H00B 109.5 . . ?
H00A C111 H00B 109.5 . . ?
O111 C111 H00C 109.5 . . ?
H00A C111 H00C 109.5 . . ?
H00B C111 H00C 109.5 . . ?
C111 O111 Co1 140.3(3) . . ?
C111 O111 H101 116(4) . . ?
Co1 O111 H101 103(4) . . ?
C444 N111 C333 119.6(6) . . ?
C444 N111 C222 122.0(6) . . ?
C333 N111 C222 118.4(5) . . ?
N111 C222 H11C 109.5 . . ?
N111 C222 H11D 109.5 . . ?
H11C C222 H11D 109.5 . . ?
N111 C222 H11E 109.5 . . ?
H11C C222 H11E 109.5 . . ?
H11D C222 H11E 109.5 . . ?
N111 C333 H22A 109.5 . . ?
N111 C333 H22B 109.5 . . ?
H22A C333 H22B 109.5 . . ?
N111 C333 H22C 109.5 . . ?
H22A C333 H22C 109.5 . . ?
H22B C333 H22C 109.5 . . ?
O222 C444 N111 125.4(7) . . ?
O222 C444 H444 117.3 . . ?
N111 C444 H444 117.3 . . ?

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 O2 0.000(2) . . . . ?
Co1 O1 C1 C3 180.000(1) . . . . ?
Co1 O4 C2 O5 0.000(1) 1_455 . . . ?
Co1 O4 C2 C5 180.000(1) 1_455 . . . ?
Co1 O5 C2 O4 0.000(1) 1_455 . . . ?
Co1 O5 C2 C5 180.000(1) 1_455 . . . ?
O2 C1 C3 C8 180.000(1) . . . . ?
O1 C1 C3 C8 0.000(2) . . . . ?
O2 C1 C3 C4 0.000(2) . . . . ?
O1 C1 C3 C4 180.000(1) . . . . ?
C8 C3 C4 C5 0.000(2) . . . . ?
C1 C3 C4 C5 180.000(1) . . . . ?
C3 C4 C5 C6 0.000(1) . . . . ?
C3 C4 C5 C2 180.000(1) . . . . ?
O4 C2 C5 C4 0.000(2) . . . . ?
O5 C2 C5 C4 180.000(1) . . . . ?
O4 C2 C5 C6 180.000(1) . . . . ?
O5 C2 C5 C6 0.000(2) . . . . ?
C4 C5 C6 C7 0.000(2) . . . . ?
C2 C5 C6 C7 180.000(1) . . . . ?
C5 C6 C7 O6 180.000(1) . . . . ?
C5 C6 C7 C8 0.000(1) . . . . ?
O6 C7 C8 C3 180.000(1) . . . . ?
C6 C7 C8 C3 0.000(1) . . . . ?
C4 C3 C8 C7 0.000(2) . . . . ?
C1 C3 C8 C7 180.000(1) . . . . ?
C10 N1 C9 C9 -56.6(3) . . . 4_565 ?
C11 N1 C9 C9 57.6(3) . . . 4_565 ?
Co1 N1 C9 C9 -179.65(7) . . . 4_565 ?
C11 N1 C10 C10 -56.2(3) . . . 4_565 ?
C9 N1 C10 C10 56.8(3) . . . 4_565 ?
Co1 N1 C10 C10 -179.98(6) . . . 4_565 ?
C10 N1 C11 C11 56.0(3) . . . 4_565 ?
C9 N1 C11 C11 -57.6(3) . . . 4_565 ?
Co1 N1 C11 C11 179.63(6) . . . 4_565 ?
C333 N111 C444 O222 0.000(2) . . . . ?
C222 N111 C444 O222 180.000(1) . . . . ?

_refine_diff_density_max         0.567
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.087



