# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_C:\Users\MATTEO1_LUS\Desktop\work\mo_40_0m_sqd
_database_code_depnum_ccdc_archive 'CCDC 1966192'
loop_
_audit_author_name
_audit_author_address
'THIRUMURUGAN PRAKASAM'
;NYUAD
United Arab Emirates
;
_audit_update_record             
;
2019-11-17 deposited with the CCDC.	2020-04-28 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            'C18 H12 Co N2 O4'
_chemical_formula_weight         379.23

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   7.3164(10)
_cell_length_b                   23.412(3)
_cell_length_c                   12.3254(17)
_cell_angle_alpha                90
_cell_angle_beta                 94.770(2)
_cell_angle_gamma                90
_cell_volume                     2103.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    634
_cell_measurement_theta_min      2
_cell_measurement_theta_max      20

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_F_000             772
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.835
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6298
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker d8 quest'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16361
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.740
_diffrn_reflns_theta_max         28.288
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5203
_reflns_number_gt                4101
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0428P)²+1.0660P] 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         5203
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.0982
_refine_ls_wR_factor_gt          0.0945
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
Co1 Co 0.73750(3) 0.36724(2) 0.45951(2) 0.01289(8) Uani 1 1 d . . . . .
C1 C 0.7759(3) 0.49097(10) 0.4357(2) 0.0282(5) Uani 1 1 d . . . . .
N2 N 0.7859(2) 0.44260(8) 0.37657(15) 0.0213(4) Uani 1 1 d . . . . .
C3 C 0.8301(3) 0.44567(12) 0.2737(2) 0.0326(6) Uani 1 1 d . . . . .
H3 H 0.835600 0.412185 0.233519 0.039 Uiso 1 1 calc R U . . .
C4 C 0.8680(3) 0.49729(15) 0.2250(3) 0.0478(8) Uani 1 1 d . . . . .
H4 H 0.899176 0.498718 0.153444 0.057 Uiso 1 1 calc R U . . .
C5 C 0.8580(4) 0.54663(13) 0.2863(3) 0.0584(11) Uani 1 1 d . . . . .
H5 H 0.882996 0.581796 0.255678 0.070 Uiso 1 1 calc R U . . .
C6 C 0.8114(4) 0.54398(11) 0.3919(3) 0.0458(8) Uani 1 1 d . . . . .
H6 H 0.803982 0.577028 0.433201 0.055 Uiso 1 1 calc R U . . .
C7 C 0.7253(3) 0.48330(10) 0.5482(2) 0.0278(5) Uani 1 1 d . . . . .
N8 N 0.6997(2) 0.42885(8) 0.57879(15) 0.0223(4) Uani 1 1 d . . . . .
C9 C 0.6521(3) 0.41786(13) 0.67979(19) 0.0337(6) Uani 1 1 d . . . . .
H9 H 0.634708 0.380116 0.700074 0.040 Uiso 1 1 calc R U . . .
C10 C 0.6279(3) 0.46079(16) 0.7547(2) 0.0506(9) Uani 1 1 d . . . . .
H10 H 0.594809 0.452116 0.824061 0.061 Uiso 1 1 calc R U . . .
C11 C 0.6538(4) 0.51624(17) 0.7243(3) 0.0597(11) Uani 1 1 d . . . . .
H11 H 0.638101 0.545749 0.773164 0.072 Uiso 1 1 calc R U . . .
C12 C 0.7032(3) 0.52833(12) 0.6215(3) 0.0486(9) Uani 1 1 d . . . . .
H12 H 0.721761 0.565927 0.600675 0.058 Uiso 1 1 calc R U . . .
O13 O 0.68052(18) 0.31348(6) 0.31649(12) 0.0204(3) Uani 1 1 d . . . . .
O14 O 0.46363(17) 0.34975(6) 0.40879(11) 0.0153(3) Uani 1 1 d . . . . .
C15 C 0.5128(2) 0.31872(8) 0.33163(15) 0.0134(4) Uani 1 1 d . . . . .
C16 C 0.3698(2) 0.28791(8) 0.26021(16) 0.0143(4) Uani 1 1 d . . . . .
C17 C 0.1840(3) 0.29723(9) 0.27186(16) 0.0170(4) Uani 1 1 d . . . . .
H17 H 0.148698 0.323628 0.322506 0.020 Uiso 1 1 calc R U . . .
C18 C 0.0515(2) 0.26706(9) 0.20772(17) 0.0198(4) Uani 1 1 d . . . . .
H18 H -0.072296 0.273880 0.214251 0.024 Uiso 1 1 calc R U . . .
C19 C 0.1047(2) 0.22668(9) 0.13384(16) 0.0160(4) Uani 1 1 d . . . . .
C20 C 0.2908(3) 0.21716(9) 0.12106(17) 0.0192(4) Uani 1 1 d . . . . .
H20 H 0.325845 0.190541 0.070772 0.023 Uiso 1 1 calc R U . . .
C21 C 0.4226(3) 0.24805(9) 0.18456(17) 0.0195(4) Uani 1 1 d . . . . .
H21 H 0.546434 0.242086 0.176542 0.023 Uiso 1 1 calc R U . . .
C22 C -0.0376(2) 0.19255(9) 0.06752(16) 0.0157(4) Uani 1 1 d . . . . .
O23 O 0.01239(17) 0.15504(6) 0.00183(11) 0.0164(3) Uani 1 1 d . . . . .
O24 O -0.20626(18) 0.20019(7) 0.07811(12) 0.0220(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 N2 2.0840(18) . ?
Co1 O14 2.0893(13) . ?
Co1 N8 2.0942(18) . ?
Co1 O23 2.1011(13) 4_666 ?
Co1 O24 2.1675(15) 4_666 ?
Co1 O13 2.1779(14) . ?
Co1 C22 2.4647(19) 4_666 ?
C1 N2 1.352(3) . ?
C1 C6 1.386(3) . ?
C1 C7 1.475(4) . ?
N2 C3 1.336(3) . ?
C3 C4 1.388(4) . ?
C4 C5 1.385(5) . ?
C5 C6 1.375(5) . ?
C7 N8 1.347(3) . ?
C7 C12 1.407(4) . ?
N8 C9 1.345(3) . ?
C9 C10 1.386(4) . ?
C10 C11 1.369(5) . ?
C11 C12 1.375(5) . ?
O13 C15 1.262(2) . ?
O14 C15 1.272(2) . ?
C15 C16 1.496(2) . ?
C16 C17 1.396(3) . ?
C16 C21 1.396(3) . ?
C17 C18 1.391(3) . ?
C18 C19 1.390(3) . ?
C19 C20 1.401(3) . ?
C19 C22 1.500(3) . ?
C20 C21 1.393(3) . ?
C22 O24 1.264(2) . ?
C22 O23 1.269(2) . ?

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
N2 Co1 O14 102.53(6) . . ?
N2 Co1 N8 78.41(8) . . ?
O14 Co1 N8 99.54(6) . . ?
N2 Co1 O23 97.69(6) . 4_666 ?
O14 Co1 O23 154.16(6) . 4_666 ?
N8 Co1 O23 100.15(6) . 4_666 ?
N2 Co1 O24 156.48(6) . 4_666 ?
O14 Co1 O24 100.52(5) . 4_666 ?
N8 Co1 O24 93.26(7) . 4_666 ?
O23 Co1 O24 61.81(5) 4_666 4_666 ?
N2 Co1 O13 96.96(7) . . ?
O14 Co1 O13 61.98(5) . . ?
N8 Co1 O13 159.83(6) . . ?
O23 Co1 O13 99.92(5) 4_666 . ?
O24 Co1 O13 97.92(6) 4_666 . ?
N2 Co1 C22 127.79(6) . 4_666 ?
O14 Co1 C22 129.11(6) . 4_666 ?
N8 Co1 C22 97.65(7) . 4_666 ?
O23 Co1 C22 30.98(6) 4_666 4_666 ?
O24 Co1 C22 30.83(6) 4_666 4_666 ?
O13 Co1 C22 100.55(6) . 4_666 ?
N2 C1 C6 121.3(3) . . ?
N2 C1 C7 115.7(2) . . ?
C6 C1 C7 123.0(3) . . ?
C3 N2 C1 119.6(2) . . ?
C3 N2 Co1 125.12(17) . . ?
C1 N2 Co1 115.20(16) . . ?
N2 C3 C4 122.0(3) . . ?
C5 C4 C3 118.0(3) . . ?
C6 C5 C4 120.5(2) . . ?
C5 C6 C1 118.6(3) . . ?
N8 C7 C12 120.2(3) . . ?
N8 C7 C1 115.47(19) . . ?
C12 C7 C1 124.3(3) . . ?
C9 N8 C7 119.5(2) . . ?
C9 N8 Co1 125.27(17) . . ?
C7 N8 Co1 115.19(16) . . ?
N8 C9 C10 122.3(3) . . ?
C11 C10 C9 118.5(3) . . ?
C10 C11 C12 120.0(3) . . ?
C11 C12 C7 119.4(3) . . ?
C15 O13 Co1 86.97(11) . . ?
C15 O14 Co1 90.67(11) . . ?
O13 C15 O14 120.32(17) . . ?
O13 C15 C16 120.48(17) . . ?
O14 C15 C16 119.19(16) . . ?
C17 C16 C21 119.95(17) . . ?
C17 C16 C15 120.24(17) . . ?
C21 C16 C15 119.76(16) . . ?
C18 C17 C16 120.02(18) . . ?
C19 C18 C17 119.86(17) . . ?
C18 C19 C20 120.60(18) . . ?
C18 C19 C22 120.00(16) . . ?
C20 C19 C22 119.40(17) . . ?
C21 C20 C19 119.22(18) . . ?
C20 C21 C16 120.33(17) . . ?
O24 C22 O23 119.96(17) . . ?
O24 C22 C19 120.51(17) . . ?
O23 C22 C19 119.52(16) . . ?
O24 C22 Co1 61.49(10) . 4_465 ?
O23 C22 Co1 58.47(9) . 4_465 ?
C19 C22 Co1 177.47(14) . 4_465 ?
C22 O23 Co1 90.54(11) . 4_465 ?
C22 O24 Co1 87.68(12) . 4_465 ?

_refine_diff_density_max         0.446
_refine_diff_density_min         -0.696
_refine_diff_density_rms         0.069

