# Supplementary Information (SI) for Green Chemistry.
# 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 2470183'
loop_
_audit_author_name
_audit_author_address
'Duo-Zhi Wang'
;Xinjiang University
China
;
_audit_update_record             
;
2025-08-29 deposited with the CCDC.	2026-01-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 Fe2 N6 O13'
_chemical_formula_weight         664.12

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   19.612(16)
_cell_length_b                   10.811(7)
_cell_length_c                   13.532(11)
_cell_angle_alpha                90
_cell_angle_beta                 123.86(3)
_cell_angle_gamma                90
_cell_volume                     2383(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7929
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      24.92

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.851
_exptl_crystal_F_000             1352
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.303
_shelx_estimated_absorpt_T_min   0.859
_shelx_estimated_absorpt_T_max   0.903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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  ccd
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19749
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.261
_diffrn_reflns_theta_max         25.078
_diffrn_reflns_theta_full        25.078
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2104
_reflns_number_gt                1781
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0629P)²+4.1754P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2104
_refine_ls_number_parameters     190
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1284
_refine_ls_wR_factor_gt          0.1074
_refine_ls_goodness_of_fit_ref   1.227
_refine_ls_restrained_S_all      1.421
_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
C1 C 0.5032(2) 0.0007(3) 0.6313(4) 0.0351(9) Uani 1 1 d . . . . .
H1 H 0.4770 -0.0758 0.6117 0.042 Uiso 1 1 calc R U . . .
C2 C 0.5963(2) 0.1345(3) 0.7055(4) 0.0342(9) Uani 1 1 d . . . . .
H2 H 0.6470 0.1740 0.7467 0.041 Uiso 1 1 calc R U . . .
C3 C 0.5072(2) 0.3216(3) 0.6275(3) 0.0205(7) Uani 1 1 d . . . . .
C4 C 0.4280(2) 0.3623(3) 0.5465(3) 0.0225(8) Uani 1 1 d . . . . .
H4 H 0.3856 0.3061 0.5021 0.027 Uiso 1 1 calc R U . . .
C5 C 0.41299(19) 0.4888(3) 0.5329(3) 0.0199(7) Uani 1 1 d . . . . .
C6 C 0.4766(2) 0.5719(3) 0.5987(3) 0.0219(7) Uani 1 1 d . . . . .
H6 H 0.4664 0.6565 0.5878 0.026 Uiso 1 1 calc R U . . .
C7 C 0.5561(2) 0.5293(3) 0.6813(3) 0.0202(7) Uani 1 1 d . . . . .
C8 C 0.5710(2) 0.4031(3) 0.6963(3) 0.0226(7) Uani 1 1 d . . . . .
H8 H 0.6234 0.3735 0.7522 0.027 Uiso 1 1 calc R U . . .
C9 C 0.6252(2) 0.6188(3) 0.7518(3) 0.0255(8) Uani 1 1 d . . . . .
C10 C 0.3277(2) 0.5361(3) 0.4456(3) 0.0261(8) Uani 1 1 d . . . . .
Fe1 Fe 0.68310(3) 0.87994(4) 0.79840(5) 0.0259(2) Uani 1 1 d . . . . .
N1 N 0.52448(17) 0.1914(3) 0.6423(3) 0.0243(7) Uani 1 1 d . . . . .
N2 N 0.4634(2) 0.1056(3) 0.5936(3) 0.0406(9) Uani 1 1 d . . . . .
N3 N 0.58566(18) 0.0136(3) 0.7015(3) 0.0305(7) Uani 1 1 d . . . . .
O1 O 0.26824(15) 0.4620(2) 0.3932(2) 0.0364(7) Uani 1 1 d . . . . .
O2 O 0.31620(15) 0.6503(2) 0.4241(2) 0.0333(6) Uani 1 1 d . . . . .
O3 O 0.60883(17) 0.7314(2) 0.7248(3) 0.0399(7) Uani 1 1 d . . . . .
O4 O 0.69406(16) 0.5773(3) 0.8317(3) 0.0431(7) Uani 1 1 d . . . . .
O5 O 0.67028(16) 0.8622(2) 0.9479(2) 0.0358(7) Uani 1 1 d . . . . .
H5A H 0.7157 0.8799 1.0120 0.054 Uiso 1 1 d R U . . .
H5B H 0.6621 0.7867 0.9559 0.054 Uiso 1 1 d R U . . .
O6 O 0.70345(18) 0.8928(3) 0.6558(3) 0.0479(8) Uani 1 1 d . . . . .
H6A H 0.7335 0.8327 0.6613 0.072 Uiso 1 1 d R U . . .
H6B H 0.7319 0.9570 0.6663 0.072 Uiso 1 1 d R U . . .
O7 O 0.7540(9) 0.7798(9) 0.5366(11) 0.115(4) Uani 0.5 1 d D . P A -1
H7A H 0.7516 0.8279 0.4628 0.173 Uiso 0.5 1 d DR U P A -1
H7B H 0.7366 0.7119 0.4915 0.173 Uiso 0.5 1 d DR U P A -1


_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
C1 N2 1.309(5) . ?
C1 N3 1.352(5) . ?
C1 H1 0.9300 . ?
C2 N3 1.319(5) . ?
C2 N1 1.323(5) . ?
C2 H2 0.9300 . ?
C3 C8 1.381(5) . ?
C3 C4 1.383(5) . ?
C3 N1 1.436(4) . ?
C4 C5 1.390(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(5) . ?
C5 C10 1.501(5) . ?
C6 C7 1.396(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.386(5) . ?
C7 C9 1.498(5) . ?
C8 H8 0.9300 . ?
C9 O4 1.252(4) . ?
C9 O3 1.260(4) . ?
C10 O1 1.259(4) . ?
C10 O2 1.260(4) . ?
Fe1 O3 2.019(3) . ?
Fe1 N3 2.161(3) 1_565 ?
Fe1 O5 2.181(3) . ?
Fe1 O6 2.181(3) . ?
Fe1 O2 2.206(3) 8_566 ?
Fe1 O1 2.229(3) 8_566 ?
N1 N2 1.360(4) . ?
N3 Fe1 2.161(3) 1_545 ?
O1 Fe1 2.229(3) 8_465 ?
O2 Fe1 2.206(3) 8_465 ?
O5 H5A 0.8501 . ?
O5 H5B 0.8501 . ?
O6 H6A 0.8527 . ?
O6 H6B 0.8526 . ?
O7 H7A 1.1030 . ?
O7 H7B 0.8927 . ?

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 C1 N3 113.8(3) . . ?
N2 C1 H1 123.1 . . ?
N3 C1 H1 123.1 . . ?
N3 C2 N1 110.3(3) . . ?
N3 C2 H2 124.8 . . ?
N1 C2 H2 124.8 . . ?
C8 C3 C4 121.8(3) . . ?
C8 C3 N1 118.5(3) . . ?
C4 C3 N1 119.7(3) . . ?
C3 C4 C5 118.7(3) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 C10 119.7(3) . . ?
C4 C5 C10 120.0(3) . . ?
C5 C6 C7 120.3(3) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 119.5(3) . . ?
C8 C7 C9 120.1(3) . . ?
C6 C7 C9 120.4(3) . . ?
C3 C8 C7 119.4(3) . . ?
C3 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
O4 C9 O3 125.1(3) . . ?
O4 C9 C7 118.4(3) . . ?
O3 C9 C7 116.5(3) . . ?
O1 C10 O2 120.2(3) . . ?
O1 C10 C5 120.2(3) . . ?
O2 C10 C5 119.6(3) . . ?
O3 Fe1 N3 94.69(13) . 1_565 ?
O3 Fe1 O5 87.90(12) . . ?
N3 Fe1 O5 95.82(12) 1_565 . ?
O3 Fe1 O6 92.95(12) . . ?
N3 Fe1 O6 87.52(13) 1_565 . ?
O5 Fe1 O6 176.48(10) . . ?
O3 Fe1 O2 118.73(11) . 8_566 ?
N3 Fe1 O2 146.48(11) 1_565 8_566 ?
O5 Fe1 O2 88.30(12) . 8_566 ?
O6 Fe1 O2 88.29(12) . 8_566 ?
O3 Fe1 O1 175.62(11) . 8_566 ?
N3 Fe1 O1 87.82(12) 1_565 8_566 ?
O5 Fe1 O1 88.28(11) . 8_566 ?
O6 Fe1 O1 90.73(12) . 8_566 ?
O2 Fe1 O1 58.99(10) 8_566 8_566 ?
C2 N1 N2 109.2(3) . . ?
C2 N1 C3 129.0(3) . . ?
N2 N1 C3 121.7(3) . . ?
C1 N2 N1 103.3(3) . . ?
C2 N3 C1 103.4(3) . . ?
C2 N3 Fe1 124.9(3) . 1_545 ?
C1 N3 Fe1 131.7(2) . 1_545 ?
C10 O1 Fe1 89.9(2) . 8_465 ?
C10 O2 Fe1 90.9(2) . 8_465 ?
C9 O3 Fe1 128.9(2) . . ?
Fe1 O5 H5A 109.3 . . ?
Fe1 O5 H5B 109.2 . . ?
H5A O5 H5B 104.5 . . ?
Fe1 O6 H6A 109.5 . . ?
Fe1 O6 H6B 109.4 . . ?
H6A O6 H6B 104.4 . . ?
H7A O7 H7B 87.8 . . ?

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
C8 C3 C4 C5 1.4(5) . . . . ?
N1 C3 C4 C5 -179.3(3) . . . . ?
C3 C4 C5 C6 0.5(5) . . . . ?
C3 C4 C5 C10 179.9(3) . . . . ?
C4 C5 C6 C7 -1.5(5) . . . . ?
C10 C5 C6 C7 179.2(3) . . . . ?
C5 C6 C7 C8 0.5(5) . . . . ?
C5 C6 C7 C9 179.4(3) . . . . ?
C4 C3 C8 C7 -2.3(5) . . . . ?
N1 C3 C8 C7 178.4(3) . . . . ?
C6 C7 C8 C3 1.3(5) . . . . ?
C9 C7 C8 C3 -177.6(3) . . . . ?
C8 C7 C9 O4 -6.8(5) . . . . ?
C6 C7 C9 O4 174.3(3) . . . . ?
C8 C7 C9 O3 172.9(3) . . . . ?
C6 C7 C9 O3 -6.0(5) . . . . ?
C6 C5 C10 O1 -173.6(3) . . . . ?
C4 C5 C10 O1 7.1(5) . . . . ?
C6 C5 C10 O2 7.2(5) . . . . ?
C4 C5 C10 O2 -172.1(3) . . . . ?
N3 C2 N1 N2 -0.4(5) . . . . ?
N3 C2 N1 C3 176.4(3) . . . . ?
C8 C3 N1 C2 -7.9(5) . . . . ?
C4 C3 N1 C2 172.8(4) . . . . ?
C8 C3 N1 N2 168.5(3) . . . . ?
C4 C3 N1 N2 -10.8(5) . . . . ?
N3 C1 N2 N1 0.3(5) . . . . ?
C2 N1 N2 C1 0.1(4) . . . . ?
C3 N1 N2 C1 -177.0(3) . . . . ?
N1 C2 N3 C1 0.6(5) . . . . ?
N1 C2 N3 Fe1 -176.2(2) . . . 1_545 ?
N2 C1 N3 C2 -0.5(5) . . . . ?
N2 C1 N3 Fe1 175.8(3) . . . 1_545 ?
O2 C10 O1 Fe1 -1.2(3) . . . 8_465 ?
C5 C10 O1 Fe1 179.6(3) . . . 8_465 ?
O1 C10 O2 Fe1 1.2(3) . . . 8_465 ?
C5 C10 O2 Fe1 -179.6(3) . . . 8_465 ?
O4 C9 O3 Fe1 -1.3(6) . . . . ?
C7 C9 O3 Fe1 179.1(2) . . . . ?

_refine_diff_density_max         0.573
_refine_diff_density_min         -0.647
_refine_diff_density_rms         0.221

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2470184'
loop_
_audit_author_name
_audit_author_address
'Duo-Zhi Wang'
;Xinjiang University
China
;
_audit_update_record             
;
2025-08-29 deposited with the CCDC.	2026-01-09 downloaded from the CCDC.
;
_audit_creation_date             2024-10-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H10 Fe N2 O6'
_chemical_formula_sum            'C11 H10 Fe N2 O6'
_chemical_formula_weight         322.06
_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 0.0181 0.0091 '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'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.758(2)
_cell_length_b                   16.767(4)
_cell_length_c                   7.3771(17)
_cell_angle_alpha                90
_cell_angle_beta                 95.384(14)
_cell_angle_gamma                90
_cell_volume                     1324.8(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    884
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      57.08
_cell_measurement_theta_min      4.12
_shelx_estimated_absorpt_T_max   0.282
_shelx_estimated_absorpt_T_min   0.231
_exptl_absorpt_coefficient_mu    9.410
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.2724
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1708 before and 0.0786 after correction.
The Ratio of minimum to maximum transmission is 0.3618.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   0.864
_exptl_transmission_factor_min   0.864
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.1973
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_number            2327
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        66.857
_diffrn_reflns_theta_max         66.857
_diffrn_reflns_theta_min         4.128
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1409
_reflns_number_total             2327
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         0.761
_refine_diff_density_min         -0.723
_refine_diff_density_rms         0.162
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1593
_refine_ls_R_factor_gt           0.1218
_refine_ls_restrained_S_all      0.954
_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)+(0.0100P)²+10.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2566
_refine_ls_wR_factor_ref         0.2793
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Rotating group:
 O5(H5A,H5B), O6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C7(H7), C9(H9)
;
_atom_sites_solution_hydrogens   mixed
_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
C1 C 0.6132(9) 0.8338(6) 0.2322(15) 0.081(3) Uani 1 1 d . . . . .
H1 H 0.5722 0.8818 0.2474 0.097 Uiso 1 1 calc R U . . .
C2 C 0.7540(11) 0.7480(6) 0.1985(18) 0.094(4) Uani 1 1 d . . . . .
H2 H 0.8316 0.7248 0.1882 0.112 Uiso 1 1 calc R U . . .
C3 C 0.6483(10) 0.7078(6) 0.1981(18) 0.094(4) Uani 1 1 d . . . . .
H3 H 0.6384 0.6530 0.1830 0.113 Uiso 1 1 calc R U . . .
C4 C 0.4279(9) 0.7473(6) 0.2380(14) 0.071(3) Uani 1 1 d . . . . .
C5 C 0.3823(9) 0.6706(6) 0.2497(14) 0.077(3) Uani 1 1 d . . . . .
H5 H 0.4369 0.6276 0.2498 0.093 Uiso 1 1 calc R U . . .
C6 C 0.2574(9) 0.6569(6) 0.2612(14) 0.070(2) Uani 1 1 d . . . . .
C7 C 0.1739(9) 0.7206(6) 0.2653(13) 0.070(2) Uani 1 1 d . . . . .
H7 H 0.0892 0.7116 0.2722 0.084 Uiso 1 1 calc R U . . .
C8 C 0.2200(9) 0.7964(6) 0.2589(13) 0.070(2) Uani 1 1 d . . . . .
C9 C 0.3437(9) 0.8112(6) 0.2454(14) 0.077(3) Uani 1 1 d . . . . .
H9 H 0.3722 0.8635 0.2412 0.092 Uiso 1 1 calc R U . . .
C10 C 0.2075(10) 0.5721(6) 0.2668(14) 0.073(2) Uani 1 1 d . . . . .
C11 C 0.1332(10) 0.8676(7) 0.2640(15) 0.084(3) Uani 1 1 d . . . . .
Fe1 Fe -0.13851(14) 0.92337(9) 0.2330(2) 0.0708(6) Uani 1 1 d . . . . .
N1 N 0.5558(7) 0.7619(5) 0.2243(12) 0.073(2) Uani 1 1 d . . . . .
N2 N 0.7342(7) 0.8280(5) 0.2160(12) 0.074(2) Uani 1 1 d . . . . .
O1 O 0.1776(7) 0.9369(4) 0.2742(13) 0.104(3) Uani 1 1 d . . . . .
O2 O 0.0194(7) 0.8525(4) 0.2517(11) 0.093(2) Uani 1 1 d . . . . .
O3 O 0.0921(6) 0.5608(4) 0.2623(10) 0.081(2) Uani 1 1 d . . . . .
O4 O 0.2836(6) 0.5146(4) 0.2768(11) 0.085(2) Uani 1 1 d . . . . .
O5 O -0.1216(7) 0.9303(4) 0.5145(9) 0.085(2) Uani 1 1 d . . . . .
H5A H -0.1345 0.9781 0.5478 0.127 Uiso 1 1 d R U . . .
H5B H -0.0465 0.9207 0.5569 0.127 Uiso 1 1 d R U . . .
O6 O -0.1233(7) 0.9314(4) -0.0437(9) 0.083(2) Uani 1 1 d . . . . .
H6A H -0.1350 0.9796 -0.0794 0.124 Uiso 1 1 d R U . . .
H6B H -0.0487 0.9209 -0.0676 0.124 Uiso 1 1 d 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
C1 H1 0.9300 . ?
C1 N1 1.352(12) . ?
C1 N2 1.322(12) . ?
C2 H2 0.9300 . ?
C2 C3 1.321(14) . ?
C2 N2 1.367(12) . ?
C3 H3 0.9300 . ?
C3 N1 1.374(13) . ?
C4 C5 1.383(13) . ?
C4 C9 1.408(13) . ?
C4 N1 1.410(12) . ?
C5 H5 0.9300 . ?
C5 C6 1.374(13) . ?
C6 C7 1.397(13) . ?
C6 C10 1.521(13) . ?
C7 H7 0.9300 . ?
C7 C8 1.367(13) . ?
C8 C9 1.365(13) . ?
C8 C11 1.519(14) . ?
C9 H9 0.9300 . ?
C10 O3 1.253(12) . ?
C10 O4 1.262(11) . ?
C11 O1 1.255(13) . ?
C11 O2 1.246(12) . ?
Fe1 N2 2.101(8) 1_455 ?
Fe1 O2 2.067(7) . ?
Fe1 O3 2.357(7) 2 ?
Fe1 O4 2.182(7) 2 ?
Fe1 O5 2.071(7) . ?
Fe1 O6 2.067(7) . ?
N2 Fe1 2.101(8) 1_655 ?
O3 Fe1 2.357(7) 2_545 ?
O4 Fe1 2.182(7) 2_545 ?
O5 H5A 0.8534 . ?
O5 H5B 0.8534 . ?
O6 H6A 0.8565 . ?
O6 H6B 0.8563 . ?

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
N1 C1 H1 123.8 . . ?
N2 C1 H1 123.8 . . ?
N2 C1 N1 112.4(8) . . ?
C3 C2 H2 124.5 . . ?
C3 C2 N2 111.1(10) . . ?
N2 C2 H2 124.5 . . ?
C2 C3 H3 126.4 . . ?
C2 C3 N1 107.3(9) . . ?
N1 C3 H3 126.4 . . ?
C5 C4 C9 118.2(9) . . ?
C5 C4 N1 121.4(9) . . ?
C9 C4 N1 120.4(9) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.0(10) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C7 120.5(9) . . ?
C5 C6 C10 120.5(9) . . ?
C7 C6 C10 119.0(8) . . ?
C6 C7 H7 120.8 . . ?
C8 C7 C6 118.3(9) . . ?
C8 C7 H7 120.8 . . ?
C7 C8 C11 120.3(9) . . ?
C9 C8 C7 122.0(9) . . ?
C9 C8 C11 117.7(9) . . ?
C4 C9 H9 120.0 . . ?
C8 C9 C4 120.0(9) . . ?
C8 C9 H9 120.0 . . ?
O3 C10 C6 119.4(9) . . ?
O3 C10 O4 121.4(9) . . ?
O4 C10 C6 119.1(9) . . ?
O1 C11 C8 119.8(9) . . ?
O2 C11 C8 116.1(10) . . ?
O2 C11 O1 124.0(11) . . ?
N2 Fe1 O3 151.7(3) 1_455 2 ?
N2 Fe1 O4 94.1(3) 1_455 2 ?
O2 Fe1 N2 95.4(3) . 1_455 ?
O2 Fe1 O3 112.9(3) . 2 ?
O2 Fe1 O4 170.5(3) . 2 ?
O2 Fe1 O5 88.3(3) . . ?
O2 Fe1 O6 87.9(3) . . ?
O4 Fe1 O3 57.7(2) 2 2 ?
O5 Fe1 N2 95.6(3) . 1_455 ?
O5 Fe1 O3 86.1(3) . 2 ?
O5 Fe1 O4 89.4(3) . 2 ?
O6 Fe1 N2 95.9(3) . 1_455 ?
O6 Fe1 O3 85.1(3) . 2 ?
O6 Fe1 O4 92.5(3) . 2 ?
O6 Fe1 O5 168.2(3) . . ?
C1 N1 C3 105.1(8) . . ?
C1 N1 C4 126.6(8) . . ?
C3 N1 C4 128.3(8) . . ?
C1 N2 C2 104.1(8) . . ?
C1 N2 Fe1 125.6(7) . 1_655 ?
C2 N2 Fe1 130.3(7) . 1_655 ?
C11 O2 Fe1 133.1(8) . . ?
C10 O3 Fe1 86.5(6) . 2_545 ?
C10 O4 Fe1 94.3(6) . 2_545 ?
Fe1 O5 H5A 109.9 . . ?
Fe1 O5 H5B 110.4 . . ?
H5A O5 H5B 104.3 . . ?
Fe1 O6 H6A 110.0 . . ?
Fe1 O6 H6B 110.7 . . ?
H6A O6 H6B 104.1 . . ?

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
C2 C3 N1 C1 2.2(14) . . . . ?
C2 C3 N1 C4 -178.4(11) . . . . ?
C3 C2 N2 C1 2.0(14) . . . . ?
C3 C2 N2 Fe1 178.2(8) . . . 1_655 ?
C4 C5 C6 C7 -1.4(16) . . . . ?
C4 C5 C6 C10 177.7(9) . . . . ?
C5 C4 C9 C8 -1.7(16) . . . . ?
C5 C4 N1 C1 -172.2(10) . . . . ?
C5 C4 N1 C3 8.7(17) . . . . ?
C5 C6 C7 C8 -0.4(15) . . . . ?
C5 C6 C10 O3 -174.2(10) . . . . ?
C5 C6 C10 O4 6.1(16) . . . . ?
C6 C7 C8 C9 1.2(15) . . . . ?
C6 C7 C8 C11 -179.7(9) . . . . ?
C6 C10 O3 Fe1 178.1(9) . . . 2_545 ?
C6 C10 O4 Fe1 -177.9(8) . . . 2_545 ?
C7 C6 C10 O3 4.9(15) . . . . ?
C7 C6 C10 O4 -174.8(10) . . . . ?
C7 C8 C9 C4 -0.1(16) . . . . ?
C7 C8 C11 O1 173.8(10) . . . . ?
C7 C8 C11 O2 -8.5(15) . . . . ?
C8 C11 O2 Fe1 -175.0(7) . . . . ?
C9 C4 C5 C6 2.5(16) . . . . ?
C9 C4 N1 C1 6.0(16) . . . . ?
C9 C4 N1 C3 -173.2(11) . . . . ?
C9 C8 C11 O1 -7.0(16) . . . . ?
C9 C8 C11 O2 170.7(10) . . . . ?
C10 C6 C7 C8 -179.5(9) . . . . ?
C11 C8 C9 C4 -179.3(9) . . . . ?
N1 C1 N2 C2 -0.5(13) . . . . ?
N1 C1 N2 Fe1 -176.9(7) . . . 1_655 ?
N1 C4 C5 C6 -179.3(10) . . . . ?
N1 C4 C9 C8 -180.0(10) . . . . ?
N2 C1 N1 C3 -1.0(13) . . . . ?
N2 C1 N1 C4 179.6(9) . . . . ?
N2 C2 C3 N1 -2.7(15) . . . . ?
O1 C11 O2 Fe1 2.6(19) . . . . ?
O3 C10 O4 Fe1 2.4(11) . . . 2_545 ?
O4 C10 O3 Fe1 -2.2(10) . . . 2_545 ?

_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 0.500 0.000 -0.929 76.4 35.9 ?
2 0.500 0.500 0.036 76.4 35.9 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
