# Supplementary Information (SI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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. 
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#######################################################################

data_21octa_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2488614'
loop_
_audit_author_name
_audit_author_address
'Ashwini Kumari Shaw'
;IIT Kanpur
India
;
_audit_update_record             
;
2025-09-16 deposited with the CCDC.	2026-03-19 downloaded from the CCDC.
;
_audit_creation_date             2025-09-16
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2023.11.24 svn.r209d9fb2 for OlexSys, GUI svn.r6869)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        EDTAQUIN
_chemical_formula_moiety         'C28 H28 N6 O6'
_chemical_formula_sum            'C28 H28 N6 O6'
_chemical_formula_weight         544.56
_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'
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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.0077(7)
_cell_length_b                   7.3991(5)
_cell_length_c                   15.8713(11)
_cell_angle_alpha                90
_cell_angle_beta                 106.143(2)
_cell_angle_gamma                90
_cell_volume                     1241.70(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5313
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      2.63
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6819
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1291 before and 0.0653 after correction.
The Ratio of minimum to maximum transmission is 0.9144.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             572
_exptl_crystal_preparation       'Layering DMF:ETHER'
_exptl_crystal_recrystallization_method 'Layering DMF:ETHER'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17658
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.047
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_min         3.060
_diffrn_ambient_temperature      273.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_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                1975
_reflns_number_total             2192
_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       'SAINT V8.41 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.41 (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.224
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0812
_refine_ls_restrained_S_all      1.224
_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)+(0.0316P)²+3.5793P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1530
_refine_ls_wR_factor_ref         0.1570
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2A), C6(H6), C7(H7), C8(H8), C9(H9), C3(H3), C5(H5)
2.c Idealised tetrahedral OH refined as rotating group with stretchable bonds:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O1 O 0.1631(2) 1.0369(3) 0.44484(15) 0.0174(6) Uani 1 1 d . . . . .
O3 O 0.3578(2) 0.4246(3) 0.43067(17) 0.0240(6) Uani 1 1 d . . . . .
O2 O 0.1090(2) 1.2016(3) 0.32175(15) 0.0187(6) Uani 1 1 d . . . . .
H2 H 0.056(4) 1.251(5) 0.3464(17) 0.028 Uiso 1 1 calc R U . . .
N1 N 0.0576(3) 0.6203(4) 0.62282(18) 0.0156(6) Uani 1 1 d . . . . .
N2 N 0.2620(3) 0.6615(4) 0.47961(18) 0.0164(6) Uani 1 1 d . . . . .
H2A H 0.249779 0.776040 0.473220 0.020 Uiso 1 1 calc R U . . .
N3 N 0.3766(3) 0.9093(4) 0.40275(19) 0.0163(6) Uani 1 1 d . . . . .
C2 C 0.1587(3) 0.3302(5) 0.6226(2) 0.0156(7) Uani 1 1 d . . . . .
C1 C 0.0801(3) 0.4467(5) 0.6542(2) 0.0164(8) Uani 1 1 d . . . . .
C6 C 0.0232(3) 0.3858(5) 0.7184(2) 0.0202(8) Uani 1 1 d . . . . .
H6 H -0.029793 0.462343 0.738441 0.024 Uiso 1 1 calc R U . . .
C7 C 0.0458(3) 0.2143(5) 0.7513(2) 0.0208(8) Uani 1 1 d . . . . .
H7 H 0.010183 0.175750 0.794961 0.025 Uiso 1 1 calc R U . . .
C8 C 0.1229(3) 0.0960(5) 0.7192(2) 0.0213(8) Uani 1 1 d . . . . .
H8 H 0.136416 -0.021217 0.740986 0.026 Uiso 1 1 calc R U . . .
C9 C 0.1776(3) 0.1514(5) 0.6570(2) 0.0185(8) Uani 1 1 d . . . . .
H9 H 0.228198 0.071666 0.636467 0.022 Uiso 1 1 calc R U . . .
C3 C 0.2196(3) 0.3966(5) 0.5618(2) 0.0178(8) Uani 1 1 d . . . . .
H3 H 0.271705 0.321706 0.540077 0.021 Uiso 1 1 calc R U . . .
C4 C 0.2011(3) 0.5744(5) 0.5351(2) 0.0161(7) Uani 1 1 d . . . . .
C5 C 0.1148(3) 0.6793(5) 0.5664(2) 0.0162(7) Uani 1 1 d . . . . .
H5 H 0.098041 0.796737 0.545528 0.019 Uiso 1 1 calc R U . . .
C10 C 0.3378(3) 0.5866(5) 0.4350(2) 0.0162(8) Uani 1 1 d . . . . .
C11 C 0.4001(3) 0.7214(5) 0.3882(2) 0.0166(8) Uani 1 1 d . . . . .
H11A H 0.490654 0.700914 0.406642 0.020 Uiso 1 1 calc R U . . .
H11B H 0.370964 0.697542 0.325666 0.020 Uiso 1 1 calc R U . . .
C12 C 0.2799(3) 1.0048(5) 0.3378(2) 0.0191(8) Uani 1 1 d . . . . .
H12A H 0.241006 0.922689 0.290333 0.023 Uiso 1 1 calc R U . . .
H12B H 0.318760 1.102199 0.313656 0.023 Uiso 1 1 calc R U . . .
C13 C 0.1780(3) 1.0827(5) 0.3751(2) 0.0140(7) Uani 1 1 d . . . . .
C14 C 0.4848(3) 1.0157(5) 0.4512(2) 0.0155(7) Uani 1 1 d . . . . .
H14A H 0.466899 1.142947 0.438993 0.019 Uiso 1 1 calc R U . . .
H14B H 0.557805 0.984397 0.431302 0.019 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
O1 C13 1.212(4) . ?
O3 C10 1.225(4) . ?
O2 H2 0.87(4) . ?
O2 C13 1.307(4) . ?
N1 C1 1.375(4) . ?
N1 C5 1.305(4) . ?
N2 H2A 0.8600 . ?
N2 C4 1.403(4) . ?
N2 C10 1.354(4) . ?
N3 C11 1.445(4) . ?
N3 C12 1.444(4) . ?
N3 C14 1.455(4) . ?
C2 C1 1.409(5) . ?
C2 C9 1.424(5) . ?
C2 C3 1.407(5) . ?
C1 C6 1.411(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.368(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.410(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.356(5) . ?
C9 H9 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.380(5) . ?
C4 C5 1.420(5) . ?
C5 H5 0.9300 . ?
C10 C11 1.516(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.519(5) . ?
C14 C14 1.510(6) 3_676 ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?

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
C13 O2 H2 109.5 . . ?
C5 N1 C1 119.2(3) . . ?
C4 N2 H2A 116.1 . . ?
C10 N2 H2A 116.1 . . ?
C10 N2 C4 127.8(3) . . ?
C11 N3 C14 116.7(3) . . ?
C12 N3 C11 119.1(3) . . ?
C12 N3 C14 116.4(3) . . ?
C1 C2 C9 118.1(3) . . ?
C3 C2 C1 119.2(3) . . ?
C3 C2 C9 122.7(3) . . ?
N1 C1 C2 120.6(3) . . ?
N1 C1 C6 119.3(3) . . ?
C2 C1 C6 120.1(3) . . ?
C1 C6 H6 119.9 . . ?
C7 C6 C1 120.1(3) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C8 120.1(3) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.7(3) . . ?
C9 C8 H8 119.7 . . ?
C2 C9 H9 119.6 . . ?
C8 C9 C2 120.9(3) . . ?
C8 C9 H9 119.6 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.0(3) . . ?
C4 C3 H3 120.5 . . ?
N2 C4 C5 116.9(3) . . ?
C3 C4 N2 125.1(3) . . ?
C3 C4 C5 118.0(3) . . ?
N1 C5 C4 123.7(3) . . ?
N1 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
O3 C10 N2 125.2(3) . . ?
O3 C10 C11 120.3(3) . . ?
N2 C10 C11 114.6(3) . . ?
N3 C11 C10 115.4(3) . . ?
N3 C11 H11A 108.4 . . ?
N3 C11 H11B 108.4 . . ?
C10 C11 H11A 108.4 . . ?
C10 C11 H11B 108.4 . . ?
H11A C11 H11B 107.5 . . ?
N3 C12 H12A 109.1 . . ?
N3 C12 H12B 109.1 . . ?
N3 C12 C13 112.7(3) . . ?
H12A C12 H12B 107.8 . . ?
C13 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
O1 C13 O2 125.3(3) . . ?
O1 C13 C12 123.5(3) . . ?
O2 C13 C12 111.3(3) . . ?
N3 C14 C14 112.0(3) . 3_676 ?
N3 C14 H14A 109.2 . . ?
N3 C14 H14B 109.2 . . ?
C14 C14 H14A 109.2 3_676 . ?
C14 C14 H14B 109.2 3_676 . ?
H14A C14 H14B 107.9 . . ?

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
O3 C10 C11 N3 -175.9(3) . . . . ?
N1 C1 C6 C7 -179.1(3) . . . . ?
N2 C4 C5 N1 -175.3(3) . . . . ?
N2 C10 C11 N3 4.1(4) . . . . ?
N3 C12 C13 O1 -15.7(5) . . . . ?
N3 C12 C13 O2 165.3(3) . . . . ?
C2 C1 C6 C7 1.1(5) . . . . ?
C2 C3 C4 N2 175.6(3) . . . . ?
C2 C3 C4 C5 -3.7(5) . . . . ?
C1 N1 C5 C4 -0.4(5) . . . . ?
C1 C2 C9 C8 -0.9(5) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C1 C6 C7 C8 -2.0(5) . . . . ?
C6 C7 C8 C9 1.4(5) . . . . ?
C7 C8 C9 C2 0.1(5) . . . . ?
C9 C2 C1 N1 -179.5(3) . . . . ?
C9 C2 C1 C6 0.3(5) . . . . ?
C9 C2 C3 C4 -176.8(3) . . . . ?
C3 C2 C1 N1 3.5(5) . . . . ?
C3 C2 C1 C6 -176.8(3) . . . . ?
C3 C2 C9 C8 176.1(3) . . . . ?
C3 C4 C5 N1 4.0(5) . . . . ?
C4 N2 C10 O3 6.0(6) . . . . ?
C4 N2 C10 C11 -173.9(3) . . . . ?
C5 N1 C1 C2 -3.4(5) . . . . ?
C5 N1 C1 C6 176.9(3) . . . . ?
C10 N2 C4 C3 7.8(5) . . . . ?
C10 N2 C4 C5 -172.9(3) . . . . ?
C11 N3 C12 C13 121.7(3) . . . . ?
C11 N3 C14 C14 -79.5(4) . . . 3_676 ?
C12 N3 C11 C10 -98.6(4) . . . . ?
C12 N3 C14 C14 131.5(4) . . . 3_676 ?
C14 N3 C11 C10 113.3(3) . . . . ?
C14 N3 C12 C13 -90.1(4) . . . . ?

_olex2_exptl_crystal_mounting_method 'Glass ring'
_olex2_submission_original_sample_id EDTAQUIN
_olex2_submission_special_instructions 'No special instructions were received'
