# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_nm226atw08_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 2091526'
loop_
_audit_author_name
_audit_author_address
'Miguel Clemente-Leon' 'Universidad de Valencia'
_audit_update_record             
;
2021-06-23 deposited with the CCDC.	2021-10-19 downloaded from the CCDC.
;
_audit_creation_date             2021-06-23
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C20 H8 Co2 N12 O8)'
_chemical_formula_sum            'C10 H4 Co N6 O4'
_chemical_formula_weight         331.12
_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      orthorhombic
_space_group_IT_number           58
_space_group_name_H-M_alt        'P n n m'
_space_group_name_Hall           '-P 2 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x, y, -z'
'x-1/2, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   9.529(2)
_cell_length_b                   10.157(2)
_cell_length_c                   7.903(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     764.9(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    910
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      22.1290
_cell_measurement_theta_min      3.2050
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.894
_exptl_absorpt_coefficient_mu    1.144
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64465
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             330
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1290
_diffrn_reflns_av_unetI/netI     0.0857
_diffrn_reflns_Laue_measured_fraction_full 0.947
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7555
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.467
_diffrn_reflns_theta_min         3.266
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector_area_resol_mean 16.0267
_diffrn_measured_fraction_theta_full 0.947
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_details      ?
_diffrn_measurement_device_type  
'SuperNova, Single source at offset), Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0798570000
_diffrn_orient_matrix_UB_12      -0.0097059000
_diffrn_orient_matrix_UB_13      -0.0305325000
_diffrn_orient_matrix_UB_21      -0.0396084000
_diffrn_orient_matrix_UB_22      0.0009419000
_diffrn_orient_matrix_UB_23      -0.0625221000
_diffrn_orient_matrix_UB_31      0.0110907000
_diffrn_orient_matrix_UB_32      0.0739228000
_diffrn_orient_matrix_UB_33      -0.0032689000
loop_
_diffrn_oxdiff_twin_id
_diffrn_oxdiff_twin_ratio
_diffrn_oxdiff_twin_reflns_isolated
_diffrn_oxdiff_twin_reflns_overlapped
1 0.5984 4529 4597
2 0.4016 4586 4597

_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                575
_reflns_number_total             800
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         4.490
_refine_diff_density_min         -1.774
_refine_diff_density_rms         0.216
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     59
_refine_ls_number_reflns         800
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1315
_refine_ls_R_factor_gt           0.1076
_refine_ls_restrained_S_all      1.125
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2829
_refine_ls_wR_factor_ref         0.2939
_refine_special_details          'Twin,Solvent Mask from OLEX'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C008-C009
 2.1 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009)
;
_atom_sites_solution_hydrogens   geom
_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
Co01 Co 0.500000 0.500000 0.500000 0.0195(8) Uani 1 4 d S T P . .
O002 O 0.4287(6) 0.6114(5) 0.7045(6) 0.0241(13) Uani 1 1 d . . . . .
N003 N 0.1902(9) 0.8966(7) 1.000000 0.0220(19) Uani 1 2 d S T P . .
N004 N 0.3506(8) 0.7441(8) 1.000000 0.0184(18) Uani 1 2 d S T P . .
C005 C 0.4574(8) 0.5655(7) 0.8481(9) 0.0193(16) Uani 1 1 d . . . . .
C006 C 0.4231(11) 0.6196(9) 1.000000 0.023(2) Uani 1 2 d S T P . .
N007 N 0.4159(11) 0.8597(10) 1.000000 0.062(4) Uani 1 2 d S T P . .
C008 C 0.2148(12) 0.7676(9) 1.000000 0.030(2) Uani 1 2 d DS T P . .
H008 H 0.145576 0.703075 1.000000 0.036 Uiso 1 2 calc RS T P . .
C009 C 0.3207(13) 0.9441(11) 1.000000 0.054(4) Uani 1 2 d DS T P . .
H009 H 0.339405 1.033965 1.000000 0.065 Uiso 1 2 calc RS 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
Co01 O002 2.087(5) 5_666 ?
Co01 O002 2.087(5) 2_665 ?
Co01 O002 2.087(5) 6_556 ?
Co01 O002 2.087(5) . ?
Co01 N003 2.094(8) 7_675 ?
Co01 N003 2.094(8) 3_546 ?
O002 C005 1.257(8) . ?
N003 C008 1.331(13) . ?
N003 C009 1.334(15) . ?
N004 C006 1.440(12) . ?
N004 N007 1.329(12) . ?
N004 C008 1.317(14) . ?
C005 C005 1.559(15) 2_665 ?
C005 C006 1.360(8) . ?
N007 C009 1.248(16) . ?
C008 H008 0.9300 . ?
C009 H009 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
O002 Co01 O002 78.5(3) 5_666 6_556 ?
O002 Co01 O002 101.5(3) 6_556 . ?
O002 Co01 O002 180.0(3) 5_666 . ?
O002 Co01 O002 101.5(3) 5_666 2_665 ?
O002 Co01 O002 180.0 6_556 2_665 ?
O002 Co01 O002 78.5(3) 2_665 . ?
O002 Co01 N003 89.4(2) . 3_546 ?
O002 Co01 N003 89.4(2) 6_556 3_546 ?
O002 Co01 N003 90.6(2) 5_666 3_546 ?
O002 Co01 N003 89.4(2) 2_665 7_675 ?
O002 Co01 N003 90.6(2) 2_665 3_546 ?
O002 Co01 N003 90.6(2) . 7_675 ?
O002 Co01 N003 89.4(2) 5_666 7_675 ?
O002 Co01 N003 90.6(2) 6_556 7_675 ?
N003 Co01 N003 180.0(4) 7_675 3_546 ?
C005 O002 Co01 115.3(5) . . ?
C008 N003 Co01 130.2(8) . 3_556 ?
C008 N003 C009 101.1(9) . . ?
C009 N003 Co01 128.7(7) . 3_556 ?
N007 N004 C006 123.5(8) . . ?
C008 N004 C006 129.1(8) . . ?
C008 N004 N007 107.4(8) . . ?
O002 C005 C005 115.5(4) . 2_665 ?
O002 C005 C006 126.5(7) . . ?
C006 C005 C005 118.1(5) . 2_665 ?
C005 C006 N004 118.0(5) . . ?
C005 C006 N004 118.0(5) 6_557 . ?
C005 C006 C005 123.9(10) 6_557 . ?
C009 N007 N004 105.5(9) . . ?
N003 C008 H008 124.7 . . ?
N004 C008 N003 110.6(9) . . ?
N004 C008 H008 124.7 . . ?
N003 C009 H009 122.3 . . ?
N007 C009 N003 115.4(10) . . ?
N007 C009 H009 122.3 . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.500 0.000 90.4 8.7 ?
2 0.500 1.000 0.500 90.4 8.7 ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method hydrothermal
