# Supplementary Information (SI) for RSC Advances.
# 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. 
# 
#######################################################################

data_dbufe_autored
_database_code_depnum_ccdc_archive 'CCDC 2446786'
loop_
_audit_author_name
_audit_author_address
'Houcine Naili'
;Faculty of Sciences of Sfax, Tunisia
Tunisia
;
_audit_update_record             
;
2025-04-25 deposited with the CCDC.	2026-04-08 downloaded from the CCDC.
;
_audit_creation_date             2022-12-30
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
''
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H16 Fe N4 O3, Cl'
_chemical_formula_sum            'C5 H16 Cl Fe N4 O3'
_chemical_formula_weight         271.52
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C5 H16 Cl1 Fe1 N4 O3'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 '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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   10.7188(3)
_cell_length_b                   11.0446(3)
_cell_length_c                   8.5086(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1007.29(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10232
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.9500
_cell_measurement_theta_min      5.4580
_shelx_estimated_absorpt_T_max   0.905
_shelx_estimated_absorpt_T_min   0.823
_exptl_absorpt_coefficient_mu    1.752
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86236
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.77a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.790
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             564
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
15 4 -1 0.0515
-15 -4 1 0.0515
0 1 12 0.0362
0 -1 -12 0.0662
0 16 -1 0.0291
0 -16 1 0.0291
7 14 -1 0.0365
-7 14 0 0.0380
-5 -15 1 0.0323
7 -14 0 0.0326

_exptl_crystal_size_max          0.116
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.058
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
14.6727 3.6297 -0.6075 0.0379 0.0455 0.9982
-14.6727 -3.6297 0.6075 -0.0379 -0.0455 -0.9982
-0.0405 0.5007 11.9820 0.6839 0.7222 -0.1039
0.0405 -0.5007 -11.9820 -0.6839 -0.7222 0.1039
0.0648 15.5555 -0.7040 0.7037 -0.6671 0.2444
-0.0648 -15.5555 0.7040 -0.7037 0.6671 -0.2444
6.5682 13.9471 -1.1647 0.5563 -0.5297 0.6403
-6.9943 13.8180 -0.0475 0.7059 -0.6668 -0.2390
-4.8009 -14.7082 1.0540 -0.6110 0.5809 -0.5377
6.8364 -13.9016 0.0642 -0.7079 0.6687 0.2275

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.898
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12256
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.987
_diffrn_reflns_theta_min         5.478
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.898
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00 -40.00   0.50    5.00    --   -7.98 -19.00-149.00   98
  2  ω     -3.00  73.00   0.50    5.00    --   -7.98  19.00  18.00  152
  3  ω      2.00  50.00   0.50    5.00    --    8.29-108.00  91.00   96
  4  ω    -89.00 -40.00   0.50    5.00    --   -7.98 -19.00  90.00   98
  5  ω    -21.00  32.00   0.50    5.00    --    8.29 -77.00  90.00  106
  6  ω     -7.00  39.00   0.50    5.00    --    8.29  57.00  90.00   92
  7  ω     -7.00  39.00   0.50    5.00    --    8.29  57.00-150.00   92
  8  ω    -89.00 -44.00   0.50    5.00    --   -7.98 -19.00 -60.00   90
  9  ω    -21.00  32.00   0.50    5.00    --    8.29 -77.00-120.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0069487000
_diffrn_orient_matrix_UB_12      0.0477583000
_diffrn_orient_matrix_UB_13      0.0550561000
_diffrn_orient_matrix_UB_21      0.0155965000
_diffrn_orient_matrix_UB_22      -0.0401457000
_diffrn_orient_matrix_UB_23      0.0620006000
_diffrn_orient_matrix_UB_31      0.0639382000
_diffrn_orient_matrix_UB_32      0.0150369000
_diffrn_orient_matrix_UB_33      -0.0090871000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.789
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.807
_reflns_number_gt                2444
_reflns_number_total             2510
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.77a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.77a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.77a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.617
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.21(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2510
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0248
_refine_ls_R_factor_gt           0.0238
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0296P)²+0.3075P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0574
_refine_ls_wR_factor_ref         0.0580
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.79(2)
 0.21(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B), N3(H3A,H3B), N4(H4A,H4B), C2(H2C,H2D), C3(H3C,H3D),
 C4(H4C,H4D), C5(H5A,H5B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Fe1 Fe 0.56977(2) 0.71121(3) 0.50530(5) 0.00532(10) Uani 1 1 d . . . . .
O1 O 0.64326(16) 0.56956(16) 0.5993(2) 0.0122(4) Uani 1 1 d . . . . .
O2 O 0.73710(17) 0.68837(16) 0.4338(3) 0.0122(4) Uani 1 1 d . . . . .
O3 O 0.84658(16) 0.53452(17) 0.5422(2) 0.0156(4) Uani 1 1 d . . . . .
N1 N 0.4095(2) 0.7084(2) 0.6170(3) 0.0113(5) Uani 1 1 d . . . . .
H1A H 0.356098 0.763460 0.574383 0.014 Uiso 1 1 calc R U . . .
H1B H 0.374159 0.633715 0.610117 0.014 Uiso 1 1 calc R U . . .
N2 N 0.6300(2) 0.8102(2) 0.6796(3) 0.0108(4) Uani 1 1 d . . . . .
H2A H 0.685570 0.767213 0.738053 0.013 Uiso 1 1 calc R U . . .
H2B H 0.669335 0.877126 0.641764 0.013 Uiso 1 1 calc R U . . .
N3 N 0.50253(19) 0.6153(2) 0.3319(3) 0.0111(4) Uani 1 1 d . . . . .
H3A H 0.565870 0.579499 0.277901 0.013 Uiso 1 1 calc R U . . .
H3B H 0.451692 0.556143 0.369934 0.013 Uiso 1 1 calc R U . . .
N4 N 0.5308(2) 0.8535(2) 0.3778(3) 0.0110(4) Uani 1 1 d . . . . .
H4A H 0.463155 0.892435 0.418089 0.013 Uiso 1 1 calc R U . . .
H4B H 0.596472 0.905727 0.378430 0.013 Uiso 1 1 calc R U . . .
C1 C 0.7481(2) 0.5928(2) 0.5253(3) 0.0115(5) Uani 1 1 d . . . . .
C2 C 0.4358(3) 0.7391(3) 0.7837(4) 0.0138(6) Uani 1 1 d . . . . .
H2C H 0.476004 0.670095 0.837864 0.017 Uiso 1 1 calc R U . . .
H2D H 0.357589 0.759635 0.839687 0.017 Uiso 1 1 calc R U . . .
C3 C 0.5224(3) 0.8471(3) 0.7793(3) 0.0137(5) Uani 1 1 d . . . . .
H3C H 0.479578 0.918205 0.733391 0.016 Uiso 1 1 calc R U . . .
H3D H 0.550797 0.868072 0.886612 0.016 Uiso 1 1 calc R U . . .
C4 C 0.4311(2) 0.6967(3) 0.2261(5) 0.0130(7) Uani 1 1 d . . . . .
H4C H 0.347024 0.712460 0.269723 0.016 Uiso 1 1 calc R U . . .
H4D H 0.421687 0.659452 0.120956 0.016 Uiso 1 1 calc R U . . .
C5 C 0.5044(3) 0.8134(3) 0.2145(3) 0.0129(6) Uani 1 1 d . . . . .
H5A H 0.583364 0.799761 0.156692 0.016 Uiso 1 1 calc R U . . .
H5B H 0.455383 0.875642 0.158067 0.016 Uiso 1 1 calc R U . . .
Cl1 Cl 0.26083(5) 0.95782(5) 0.49651(11) 0.01463(13) 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
Fe1 O1 1.9257(18) . ?
Fe1 O2 1.9107(18) . ?
Fe1 N1 1.963(2) . ?
Fe1 N2 1.953(2) . ?
Fe1 N3 1.954(2) . ?
Fe1 N4 1.955(2) . ?
Fe1 C1 2.322(2) . ?
O1 C1 1.314(3) . ?
O2 C1 1.317(3) . ?
O3 C1 1.245(3) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 C2 1.485(4) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 C3 1.488(4) . ?
N3 H3A 0.9100 . ?
N3 H3B 0.9100 . ?
N3 C4 1.485(4) . ?
N4 H4A 0.9100 . ?
N4 H4B 0.9100 . ?
N4 C5 1.486(4) . ?
C2 H2C 0.9900 . ?
C2 H2D 0.9900 . ?
C2 C3 1.511(4) . ?
C3 H3C 0.9900 . ?
C3 H3D 0.9900 . ?
C4 H4C 0.9900 . ?
C4 H4D 0.9900 . ?
C4 C5 1.512(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?

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 Fe1 N1 98.29(9) . . ?
O1 Fe1 N2 90.24(9) . . ?
O1 Fe1 N3 91.38(9) . . ?
O1 Fe1 N4 166.20(9) . . ?
O1 Fe1 C1 34.45(8) . . ?
O2 Fe1 O1 68.97(8) . . ?
O2 Fe1 N1 166.75(9) . . ?
O2 Fe1 N2 90.33(9) . . ?
O2 Fe1 N3 91.96(9) . . ?
O2 Fe1 N4 97.47(9) . . ?
O2 Fe1 C1 34.54(9) . . ?
N1 Fe1 C1 132.54(9) . . ?
N2 Fe1 N1 85.99(10) . . ?
N2 Fe1 N3 177.56(9) . . ?
N2 Fe1 N4 92.39(9) . . ?
N2 Fe1 C1 89.30(9) . . ?
N3 Fe1 N1 91.97(9) . . ?
N3 Fe1 N4 86.46(9) . . ?
N3 Fe1 C1 93.07(9) . . ?
N4 Fe1 N1 95.40(9) . . ?
N4 Fe1 C1 132.00(9) . . ?
C1 O1 Fe1 89.53(14) . . ?
C1 O2 Fe1 90.10(15) . . ?
Fe1 N1 H1A 110.3 . . ?
Fe1 N1 H1B 110.3 . . ?
H1A N1 H1B 108.6 . . ?
C2 N1 Fe1 107.03(17) . . ?
C2 N1 H1A 110.3 . . ?
C2 N1 H1B 110.3 . . ?
Fe1 N2 H2A 109.8 . . ?
Fe1 N2 H2B 109.8 . . ?
H2A N2 H2B 108.3 . . ?
C3 N2 Fe1 109.28(17) . . ?
C3 N2 H2A 109.8 . . ?
C3 N2 H2B 109.8 . . ?
Fe1 N3 H3A 110.0 . . ?
Fe1 N3 H3B 110.0 . . ?
H3A N3 H3B 108.3 . . ?
C4 N3 Fe1 108.62(18) . . ?
C4 N3 H3A 110.0 . . ?
C4 N3 H3B 110.0 . . ?
Fe1 N4 H4A 110.0 . . ?
Fe1 N4 H4B 110.0 . . ?
H4A N4 H4B 108.3 . . ?
C5 N4 Fe1 108.65(16) . . ?
C5 N4 H4A 110.0 . . ?
C5 N4 H4B 110.0 . . ?
O1 C1 Fe1 56.02(11) . . ?
O1 C1 O2 111.3(2) . . ?
O2 C1 Fe1 55.36(12) . . ?
O3 C1 Fe1 176.2(2) . . ?
O3 C1 O1 124.7(2) . . ?
O3 C1 O2 124.0(2) . . ?
N1 C2 H2C 110.6 . . ?
N1 C2 H2D 110.6 . . ?
N1 C2 C3 105.8(3) . . ?
H2C C2 H2D 108.7 . . ?
C3 C2 H2C 110.6 . . ?
C3 C2 H2D 110.6 . . ?
N2 C3 C2 105.9(2) . . ?
N2 C3 H3C 110.6 . . ?
N2 C3 H3D 110.6 . . ?
C2 C3 H3C 110.6 . . ?
C2 C3 H3D 110.6 . . ?
H3C C3 H3D 108.7 . . ?
N3 C4 H4C 110.4 . . ?
N3 C4 H4D 110.4 . . ?
N3 C4 C5 106.7(2) . . ?
H4C C4 H4D 108.6 . . ?
C5 C4 H4C 110.4 . . ?
C5 C4 H4D 110.4 . . ?
N4 C5 C4 107.0(3) . . ?
N4 C5 H5A 110.3 . . ?
N4 C5 H5B 110.3 . . ?
C4 C5 H5A 110.3 . . ?
C4 C5 H5B 110.3 . . ?
H5A C5 H5B 108.6 . . ?

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
Fe1 O1 C1 O2 -2.7(2) . . . . ?
Fe1 O1 C1 O3 175.4(3) . . . . ?
Fe1 O2 C1 O1 2.7(2) . . . . ?
Fe1 O2 C1 O3 -175.4(3) . . . . ?
Fe1 N1 C2 C3 45.8(2) . . . . ?
Fe1 N2 C3 C2 37.9(3) . . . . ?
Fe1 N3 C4 C5 39.9(3) . . . . ?
Fe1 N4 C5 C4 39.1(2) . . . . ?
N1 C2 C3 N2 -54.7(3) . . . . ?
N3 C4 C5 N4 -51.7(3) . . . . ?

_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop in perfluoroether oil'
_olex2_submission_original_sample_id DBUFe
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.403
_oxdiff_exptl_absorpt_empirical_full_min 0.724
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.79(2)
2 0.21(2)

