# Supplementary Information (SI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_1LTP
_database_code_depnum_ccdc_archive 'CCDC 2470382'
loop_
_audit_author_name
_audit_author_address
'Jiong-Peng Zhao'
;Tianjin University Of Technology
China
;
_audit_update_record             
;
2025-07-07 deposited with the CCDC.	2025-09-15 downloaded from the CCDC.
;
_audit_creation_date             2025-06-02
_audit_creation_method           
;
Olex2 1.5-ac6-020
(compiled 2024.02.14 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6966)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H9 Fe3 O18, C3 H12 N2, H2 O'
_chemical_formula_sum            'C12 H23 Fe3 N2 O19'
_chemical_formula_weight         666.87
_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'
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      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                   14.2657(10)
_cell_length_b                   8.2582(5)
_cell_length_c                   21.5884(12)
_cell_angle_alpha                90
_cell_angle_beta                 102.732(6)
_cell_angle_gamma                90
_cell_volume                     2480.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8565
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      30.0410
_cell_measurement_theta_min      3.2670
_shelx_estimated_absorpt_T_max   0.825
_shelx_estimated_absorpt_T_min   0.712
_exptl_absorpt_coefficient_mu    1.819
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            BLACK
_exptl_crystal_colour_primary    BLACK
_exptl_crystal_density_diffrn    1.786
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1356
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.901
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6438
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.863
_diffrn_reflns_theta_min         3.129
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -29.00   0.00   0.50    3.32    --    0.00 -37.00  60.00   58
  2  ω    -34.00   1.00   0.50    3.32    --    0.00  77.00 -90.00   70
  3  ω     16.00  88.00   0.50    3.32    --    0.00  77.00 -90.00  144
  4  ω    -28.00  49.00   0.50    3.32    --    0.00  57.00 150.00  154
  5  ω    -13.00  12.00   0.50    3.32    --    0.00  57.00   0.00   50
  6  ω     57.00  87.00   0.50    3.32    --    0.00  57.00   0.00   60
  7  ω    -89.00 -50.00   0.50    3.32    --    0.00 -37.00  60.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual offset/far'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0428318000
_diffrn_orient_matrix_UB_12      -0.0393792000
_diffrn_orient_matrix_UB_13      -0.0157186000
_diffrn_orient_matrix_UB_21      -0.0246094000
_diffrn_orient_matrix_UB_22      0.0337035000
_diffrn_orient_matrix_UB_23      0.0221405000
_diffrn_orient_matrix_UB_31      -0.0125798000
_diffrn_orient_matrix_UB_32      0.0684594000
_diffrn_orient_matrix_UB_33      -0.0199545000
_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              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5227
_reflns_number_total             6438
_reflns_special_details          
;
 _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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         2.287
_refine_diff_density_min         -1.323
_refine_diff_density_rms         0.221
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         6438
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0764
_refine_ls_restrained_S_all      1.115
_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)+(0.0921P)²+21.8890P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2293
_refine_ls_wR_factor_ref         0.2352
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.578(5)
 0.422(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
3. Uiso/Uaniso restraints and constraints
O5 \\sim O4 \\sim C5 \\sim C10: within 3.8A with sigma of 0.01 and sigma for
terminal atoms of 0.03 within 3.8A
Uanis(C6) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(O5) \\sim Ueq, Uanis(O9) \\sim
Ueq, Uanis(C4) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(O4)
\\sim Ueq, Uanis(O15) \\sim Ueq: with sigma of 0.001 and sigma for terminal
atoms of 0.002
4.a Riding coordinates:
 O1(H1F,H1G)
4.b Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), C1(H1D,H1E), C2(H2C,H2D)
4.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C5(H5), C10(H10), C7(H7), C8(H8), C6(H6), C12(H12), C11(H11), C4(H4)
4.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C3(H3A,H3B,H3C)
;
_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
Fe3 Fe 0.25035(5) 0.75732(9) 0.49842(3) 0.0046(2) Uani 1 1 d . . . . .
Fe1 Fe 0.63934(7) 0.74795(9) 0.66959(4) 0.0058(2) Uani 1 1 d . . . . .
Fe2 Fe 0.13691(7) 0.26371(10) 0.66240(4) 0.0064(2) Uani 1 1 d . . . . .
O5 O 0.1623(3) 0.6644(5) 0.5496(2) 0.0084(8) Uani 1 1 d . U . . .
O6 O 0.2765(3) 0.9573(5) 0.55382(19) 0.0087(8) Uani 1 1 d . . . . .
O13 O 0.3634(3) 0.6456(5) 0.5548(2) 0.0107(8) Uani 1 1 d . . . . .
O8 O 0.1353(3) 0.8687(5) 0.4449(2) 0.0103(8) Uani 1 1 d . . . . .
O11 O 0.3385(3) 0.8515(5) 0.44756(19) 0.0087(8) Uani 1 1 d . . . . .
O16 O 0.2275(3) 0.5606(6) 0.4426(2) 0.0114(8) Uani 1 1 d . . . . .
O12 O 0.3859(3) 1.0421(5) 0.38952(19) 0.0103(8) Uani 1 1 d . . . . .
O9 O -0.0166(3) 0.8671(5) 0.3896(2) 0.0106(8) Uani 1 1 d . U . . .
O7 O 0.2333(3) 1.1535(5) 0.6114(2) 0.0111(8) Uani 1 1 d . . . . .
O10 O 0.2720(3) 0.3645(6) 0.3856(2) 0.0146(9) Uani 1 1 d . . . . .
O4 O 0.1091(3) 0.4646(5) 0.6007(2) 0.0137(9) Uani 1 1 d . U . . .
O14 O 0.5091(3) 0.6424(5) 0.6183(2) 0.0140(9) Uani 1 1 d . . . . .
O18 O 0.6395(4) 0.5334(6) 0.7241(2) 0.0185(10) Uani 1 1 d . . . . .
O19 O 0.7235(3) 0.3389(6) 0.7822(2) 0.0166(9) Uani 1 1 d . . . . .
O15 O 0.5705(3) 0.8726(6) 0.7328(2) 0.0150(9) Uani 1 1 d . U . . .
O17 O 0.4603(4) 0.8876(6) 0.7905(2) 0.0190(10) Uani 1 1 d . . . . .
C9 C 0.3280(5) 0.9852(7) 0.4189(3) 0.0112(11) Uani 1 1 d . U . . .
H9 H 0.272033 1.046693 0.419941 0.013 Uiso 1 1 calc R U . . .
C5 C 0.1664(5) 0.5216(7) 0.5714(3) 0.0120(11) Uani 1 1 d . U . . .
H5 H 0.217103 0.453812 0.564708 0.014 Uiso 1 1 calc R U . . .
C10 C 0.4462(4) 0.7028(7) 0.5756(3) 0.0085(10) Uani 1 1 d . U . . .
H10 H 0.461809 0.800557 0.557017 0.010 Uiso 1 1 calc R U . . .
C7 C 0.0559(4) 0.7989(7) 0.4212(3) 0.0086(11) Uani 1 1 d . . . . .
H7 H 0.051844 0.685840 0.428252 0.010 Uiso 1 1 calc R U . . .
O3 O 0.1568(4) 0.0816(6) 0.7312(2) 0.0208(11) Uani 1 1 d . . . . .
C8 C 0.2137(5) 1.0275(7) 0.5790(3) 0.0103(11) Uani 1 1 d . U . . .
H8 H 0.150987 0.982713 0.572831 0.012 Uiso 1 1 calc R U . . .
C6 C 0.2917(5) 0.4865(7) 0.4203(3) 0.0095(10) Uani 1 1 d . U . . .
H6 H 0.356013 0.525199 0.430352 0.011 Uiso 1 1 calc R U . . .
O2 O 0.2363(4) -0.1131(6) 0.7903(2) 0.0190(10) Uani 1 1 d . . . . .
C12 C 0.7173(4) 0.4707(7) 0.7528(3) 0.0129(11) Uani 1 1 d . . . . .
H12 H 0.775204 0.526931 0.752231 0.015 Uiso 1 1 calc R U . . .
C11 C 0.5052(5) 0.8138(9) 0.7548(3) 0.0177(14) Uani 1 1 d . . . . .
H11 H 0.487336 0.704848 0.744029 0.021 Uiso 1 1 calc R U . . .
C4 C 0.2324(5) 0.0037(7) 0.7526(3) 0.0137(11) Uani 1 1 d . U . . .
H4 H 0.289371 0.034510 0.739804 0.016 Uiso 1 1 calc R U . . .
N2 N -0.0584(4) -0.3146(7) 0.6685(3) 0.0200(12) Uani 1 1 d . . . . .
H2A H -0.119961 -0.311056 0.673611 0.024 Uiso 1 1 calc R U . . .
H2B H -0.037187 -0.418417 0.675177 0.024 Uiso 1 1 calc R U . . .
N1 N 0.0599(5) -0.1488(7) 0.8312(3) 0.0238(13) Uani 1 1 d . . . . .
H1A H 0.120474 -0.133565 0.825299 0.029 Uiso 1 1 calc R U . . .
H1B H 0.062861 -0.190112 0.870679 0.029 Uiso 1 1 calc R U . . .
H1C H 0.028290 -0.052293 0.827405 0.029 Uiso 1 1 calc R U . . .
C1 C 0.0077(6) -0.2634(8) 0.7828(3) 0.0192(13) Uani 1 1 d . . . . .
H1D H -0.058315 -0.278283 0.789258 0.023 Uiso 1 1 calc R U . . .
H1E H 0.040337 -0.369868 0.788897 0.023 Uiso 1 1 calc R U . . .
O1 O 0.0615(5) -0.3309(9) 0.9369(3) 0.0472(17) Uani 1 1 d . . . . .
H1F H 0.095639 -0.414907 0.931410 0.071 Uiso 1 1 d R U . . .
H1G H 0.008439 -0.380087 0.921330 0.071 Uiso 1 1 d R U . . .
C2 C 0.0022(6) -0.2080(9) 0.7162(3) 0.0249(15) Uani 1 1 d . . . . .
H2C H -0.024301 -0.096783 0.711195 0.030 Uiso 1 1 calc R U . . .
H2D H 0.067848 -0.204357 0.708145 0.030 Uiso 1 1 calc R U . . .
C3 C -0.0568(7) -0.2652(11) 0.6000(4) 0.0334(17) Uani 1 1 d . . . . .
H3A H -0.082139 -0.354054 0.570991 0.050 Uiso 1 1 calc R U . . .
H3B H 0.009421 -0.241579 0.597021 0.050 Uiso 1 1 calc R U . . .
H3C H -0.096615 -0.168583 0.588233 0.050 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
Fe3 O5 1.999(4) . ?
Fe3 O6 2.025(4) . ?
Fe3 O13 2.017(5) . ?
Fe3 O8 2.010(4) . ?
Fe3 O11 2.000(4) . ?
Fe3 O16 2.006(4) . ?
Fe1 O12 2.136(4) 3_676 ?
Fe1 O10 2.132(4) 3_666 ?
Fe1 O14 2.129(5) . ?
Fe1 O18 2.127(5) . ?
Fe1 O19 2.140(5) 2_656 ?
Fe1 O15 2.115(4) . ?
Fe2 O9 2.127(5) 3_566 ?
Fe2 O7 2.145(4) 1_545 ?
Fe2 O4 2.109(5) . ?
Fe2 O17 2.151(4) 2_546 ?
Fe2 O3 2.089(5) . ?
Fe2 O2 2.130(5) 2_556 ?
O5 C5 1.266(7) . ?
O6 C8 1.284(7) . ?
O13 C10 1.260(7) . ?
O8 C7 1.273(7) . ?
O11 C9 1.258(7) . ?
O16 C6 1.281(7) . ?
O12 C9 1.240(7) . ?
O9 C7 1.241(7) . ?
O7 C8 1.251(7) . ?
O10 C6 1.250(7) . ?
O4 C5 1.232(7) . ?
O14 C10 1.241(7) . ?
O18 C12 1.257(8) . ?
O19 C12 1.253(8) . ?
O15 C11 1.236(8) . ?
O17 C11 1.262(8) . ?
C9 H9 0.9500 . ?
C5 H5 0.9500 . ?
C10 H10 0.9500 . ?
C7 H7 0.9500 . ?
O3 C4 1.253(8) . ?
C8 H8 0.9500 . ?
C6 H6 0.9500 . ?
O2 C4 1.253(7) . ?
C12 H12 0.9500 . ?
C11 H11 0.9500 . ?
C4 H4 0.9500 . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 C2 1.479(9) . ?
N2 C3 1.539(9) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N1 C1 1.484(9) . ?
C1 H1D 0.9900 . ?
C1 H1E 0.9900 . ?
C1 C2 1.494(10) . ?
O1 H1F 0.8699 . ?
O1 H1G 0.8599 . ?
C2 H2C 0.9900 . ?
C2 H2D 0.9900 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?

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
O5 Fe3 O6 92.51(16) . . ?
O5 Fe3 O13 90.38(17) . . ?
O5 Fe3 O8 87.73(17) . . ?
O5 Fe3 O11 179.68(17) . . ?
O5 Fe3 O16 88.97(17) . . ?
O13 Fe3 O6 89.86(18) . . ?
O8 Fe3 O6 89.27(18) . . ?
O8 Fe3 O13 177.89(15) . . ?
O11 Fe3 O6 87.17(17) . . ?
O11 Fe3 O13 89.65(17) . . ?
O11 Fe3 O8 92.23(17) . . ?
O11 Fe3 O16 91.36(18) . . ?
O16 Fe3 O6 178.47(16) . . ?
O16 Fe3 O13 89.71(18) . . ?
O16 Fe3 O8 91.21(18) . . ?
O12 Fe1 O19 91.22(19) 3_676 2_656 ?
O10 Fe1 O12 93.59(18) 3_666 3_676 ?
O10 Fe1 O19 80.36(18) 3_666 2_656 ?
O14 Fe1 O12 90.51(17) . 3_676 ?
O14 Fe1 O10 95.10(18) . 3_666 ?
O14 Fe1 O19 175.24(18) . 2_656 ?
O18 Fe1 O12 170.55(18) . 3_676 ?
O18 Fe1 O10 91.01(19) . 3_666 ?
O18 Fe1 O14 80.85(18) . . ?
O18 Fe1 O19 97.7(2) . 2_656 ?
O15 Fe1 O12 87.08(17) . 3_676 ?
O15 Fe1 O10 171.49(19) . 3_666 ?
O15 Fe1 O14 93.37(19) . . ?
O15 Fe1 O18 89.59(19) . . ?
O15 Fe1 O19 91.15(19) . 2_656 ?
O9 Fe2 O7 92.75(16) 3_566 1_545 ?
O9 Fe2 O17 87.79(18) 3_566 2_546 ?
O9 Fe2 O2 175.62(17) 3_566 2_556 ?
O7 Fe2 O17 176.28(18) 1_545 2_546 ?
O4 Fe2 O9 92.80(18) . 3_566 ?
O4 Fe2 O7 93.56(17) . 1_545 ?
O4 Fe2 O17 82.73(18) . 2_546 ?
O4 Fe2 O2 87.07(19) . 2_556 ?
O3 Fe2 O9 88.67(19) . 3_566 ?
O3 Fe2 O7 93.28(18) . 1_545 ?
O3 Fe2 O4 172.93(18) . . ?
O3 Fe2 O17 90.42(19) . 2_546 ?
O3 Fe2 O2 92.0(2) . 2_556 ?
O2 Fe2 O7 82.89(18) 2_556 1_545 ?
O2 Fe2 O17 96.54(19) 2_556 2_546 ?
C5 O5 Fe3 125.5(4) . . ?
C8 O6 Fe3 124.2(4) . . ?
C10 O13 Fe3 127.3(4) . . ?
C7 O8 Fe3 124.4(4) . . ?
C9 O11 Fe3 126.1(4) . . ?
C6 O16 Fe3 125.3(4) . . ?
C9 O12 Fe1 124.7(4) . 3_676 ?
C7 O9 Fe2 122.5(4) . 3_566 ?
C8 O7 Fe2 123.4(4) . 1_565 ?
C6 O10 Fe1 127.0(4) . 3_666 ?
C5 O4 Fe2 124.8(4) . . ?
C10 O14 Fe1 128.9(4) . . ?
C12 O18 Fe1 120.6(4) . . ?
C12 O19 Fe1 120.4(4) . 2_646 ?
C11 O15 Fe1 123.6(4) . . ?
C11 O17 Fe2 121.7(4) . 2_556 ?
O11 C9 H9 117.9 . . ?
O12 C9 O11 124.3(6) . . ?
O12 C9 H9 117.9 . . ?
O5 C5 H5 117.8 . . ?
O4 C5 O5 124.4(6) . . ?
O4 C5 H5 117.8 . . ?
O13 C10 H10 117.2 . . ?
O14 C10 O13 125.6(5) . . ?
O14 C10 H10 117.2 . . ?
O8 C7 H7 117.5 . . ?
O9 C7 O8 125.1(6) . . ?
O9 C7 H7 117.5 . . ?
C4 O3 Fe2 127.1(4) . . ?
O6 C8 H8 119.3 . . ?
O7 C8 O6 121.4(6) . . ?
O7 C8 H8 119.3 . . ?
O16 C6 H6 119.2 . . ?
O10 C6 O16 121.6(6) . . ?
O10 C6 H6 119.2 . . ?
C4 O2 Fe2 126.2(5) . 2_546 ?
O18 C12 H12 117.9 . . ?
O19 C12 O18 124.3(6) . . ?
O19 C12 H12 117.9 . . ?
O15 C11 O17 124.9(7) . . ?
O15 C11 H11 117.5 . . ?
O17 C11 H11 117.5 . . ?
O3 C4 O2 123.1(6) . . ?
O3 C4 H4 118.4 . . ?
O2 C4 H4 118.4 . . ?
H2A N2 H2B 107.9 . . ?
C2 N2 H2A 109.1 . . ?
C2 N2 H2B 109.1 . . ?
C2 N2 C3 112.4(6) . . ?
C3 N2 H2A 109.1 . . ?
C3 N2 H2B 109.1 . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
N1 C1 H1D 108.9 . . ?
N1 C1 H1E 108.9 . . ?
N1 C1 C2 113.3(6) . . ?
H1D C1 H1E 107.7 . . ?
C2 C1 H1D 108.9 . . ?
C2 C1 H1E 108.9 . . ?
H1F O1 H1G 92.4 . . ?
N2 C2 C1 112.7(6) . . ?
N2 C2 H2C 109.0 . . ?
N2 C2 H2D 109.0 . . ?
C1 C2 H2C 109.0 . . ?
C1 C2 H2D 109.0 . . ?
H2C C2 H2D 107.8 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C7 H7 O4 0.95 2.56 3.164(7) 121.4 3_566 yes
C8 H8 O9 0.95 2.56 3.158(7) 121.0 3_576 yes
C12 H12 O19 0.95 2.68 3.288(8) 122.2 2_656 yes
C11 H11 O3 0.95 2.46 3.069(8) 122.1 2_556 yes
N2 H2A O10 0.91 2.30 3.041(8) 137.9 3_556 yes
N2 H2A O19 0.91 2.29 3.065(8) 142.8 2_546 yes
N2 H2B O17 0.91 1.99 2.871(8) 162.6 2_536 yes
N1 H1A O2 0.91 1.97 2.861(8) 165.6 . yes
N1 H1B O1 0.91 1.85 2.728(10) 162.7 . yes
N1 H1C O14 0.91 2.13 2.900(7) 142.3 2_546 yes
N1 H1C O18 0.91 2.51 3.207(8) 133.8 2_546 yes
O1 H1F O6 0.87 2.07 2.868(8) 152.3 2_536 yes
O1 H1G O11 0.86 2.62 3.246(8) 130.6 4_566 yes
O1 H1G O12 0.86 2.19 3.039(8) 170.2 4_566 yes
C2 H2C O18 0.99 2.61 3.298(9) 126.4 2_546 yes

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
Fe3 O5 C5 O4 -177.0(5) . . . . ?
Fe3 O6 C8 O7 -178.0(4) . . . . ?
Fe3 O13 C10 O14 167.2(5) . . . . ?
Fe3 O8 C7 O9 177.8(4) . . . . ?
Fe3 O11 C9 O12 177.5(4) . . . . ?
Fe3 O16 C6 O10 -179.8(4) . . . . ?
Fe1 O12 C9 O11 171.3(4) 3_676 . . . ?
Fe1 O10 C6 O16 167.7(4) 3_666 . . . ?
Fe1 O14 C10 O13 -166.8(4) . . . . ?
Fe1 O18 C12 O19 -174.9(5) . . . . ?
Fe1 O19 C12 O18 -179.0(5) 2_646 . . . ?
Fe1 O15 C11 O17 -177.0(5) . . . . ?
Fe2 O9 C7 O8 168.4(4) 3_566 . . . ?
Fe2 O7 C8 O6 -173.7(4) 1_565 . . . ?
Fe2 O4 C5 O5 -158.8(5) . . . . ?
Fe2 O17 C11 O15 -170.5(5) 2_556 . . . ?
Fe2 O3 C4 O2 -174.0(5) . . . . ?
Fe2 O2 C4 O3 -172.6(5) 2_546 . . . ?
N1 C1 C2 N2 -174.1(5) . . . . ?
C3 N2 C2 C1 -175.1(7) . . . . ?

_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 1.502
_oxdiff_exptl_absorpt_empirical_full_min 0.757
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.578(5)
2 0.422(5)
####################################################################### 
# 
# 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_2LTP
_database_code_depnum_ccdc_archive 'CCDC 2470384'
loop_
_audit_author_name
_audit_author_address
'Jiong-Peng Zhao'
;Tianjin University Of Technology
China
;
_audit_update_record             
;
2025-07-07 deposited with the CCDC.	2025-09-15 downloaded from the CCDC.
;
_audit_creation_date             2025-06-02
_audit_creation_method           
;
Olex2 1.5-ac6-020
(compiled 2024.02.14 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6966)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H9 Fe3 O18, C4 H14 N2'
_chemical_formula_sum            'C13 H23 Fe3 N2 O18'
_chemical_formula_weight         662.88
_chemical_melting_point          ?
_chemical_oxdiff_formula         C13H23Fe3N2O18
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'
Fe Fe 0.3463 0.8444 '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                   14.2147(9)
_cell_length_b                   8.3281(4)
_cell_length_c                   21.3984(13)
_cell_angle_alpha                90
_cell_angle_beta                 102.558(6)
_cell_angle_gamma                90
_cell_volume                     2472.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10852
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.9240
_cell_measurement_theta_min      3.1780
_shelx_estimated_absorpt_T_max   0.463
_shelx_estimated_absorpt_T_min   0.362
_exptl_absorpt_coefficient_mu    1.821
_exptl_absorpt_correction_T_max  0.440
_exptl_absorpt_correction_T_min  0.238
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.144a (Rigaku Oxford Diffraction, 2024)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.781
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1348
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
14 3 -24 0.2367
9 -3 -28 0.1942
7 -5 -27 0.1892
-10 2 28 0.4659
10 10 -1 0.3453
11 -1 -28 0.2058
-12 2 27 0.4694
2 -5 -27 0.2217
15 0 -25 0.2329
15 1 -24 0.2340
11 6 15 0.4636
-11 2 28 0.4537
5 7 -24 0.3069
6 -8 -22 0.1664
10 10 -12 0.3248
-14 0 -16 0.4471
2 12 -2 0.4790
9 8 -20 0.2733
5 -10 -16 0.2275
9 3 22 0.5572
-4 -3 -26 0.2457
-17 -3 -9 0.5496
7 -10 -11 0.2666
-19 3 2 0.6045
9 -2 23 0.5651

_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.5
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
13.8542 3.3174 -24.1032 0.3790 0.2273 0.8971
9.3334 -3.3116 -27.7379 -0.1579 -0.0955 0.9828
7.2350 -5.0703 -26.6918 -0.3089 -0.1862 0.9327
-10.4004 2.2480 27.9189 0.0685 0.0417 -0.9968
9.7387 10.2106 -0.6078 0.8534 0.5130 0.0929
10.6183 -0.5976 -28.3894 0.0726 -0.0304 0.9969
-11.6032 2.2120 27.1389 0.0704 -0.0303 -0.9971
1.5511 -4.6018 -27.4931 -0.2596 -0.4690 0.8442
14.8657 0.4539 -24.5604 0.1387 0.2498 0.9583
15.0242 0.5495 -24.3354 0.1455 0.2622 0.9540
10.9000 6.4917 15.0173 0.4647 0.8389 -0.2832
-10.7874 1.5716 28.0162 0.0114 0.0211 -0.9997
5.4652 7.2228 -23.5797 0.7146 -0.1388 0.6856
5.7752 -7.7248 -22.3640 -0.5516 -0.1904 0.8121
9.6241 9.7287 -11.6368 0.8650 0.2979 0.4037
-14.4300 0.3676 -15.6990 0.1205 -0.9788 0.1654
1.9274 11.6755 -2.0959 0.9922 0.1220 -0.0264
8.8907 7.9760 -20.1291 0.7582 0.0934 0.6453
5.4398 -9.8472 -15.6740 -0.7618 -0.0936 0.6410
9.3221 3.3311 21.6410 0.1686 0.8692 -0.4649
-4.2129 -3.1654 -26.2909 -0.1381 -0.7122 0.6883
-16.8779 -2.9488 -8.5244 -0.1904 -0.9806 -0.0462
7.1544 -10.4127 -10.9780 -0.8335 0.0726 0.5477
-18.9965 3.3312 1.9569 0.2917 -0.8475 -0.4434
9.1777 -2.0877 22.6548 -0.2929 0.8490 -0.4398

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            27803
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.701
_diffrn_reflns_theta_min         3.117
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.909
_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 -60.00   0.50    1.92    --    0.00 -57.00 -60.00   58
  2  ω    -23.00   3.00   0.50    1.92    --    0.00 -57.00 -60.00   52
  3  ω    -47.00  -3.00   0.50    1.92    --    0.00 -37.00  90.00   88
  4  ω    -27.00  -1.00   0.50    1.92    --    0.00  57.00-150.00   52
  5  ω      1.00  87.00   0.50    1.92    --    0.00  57.00-150.00  172
  6  ω    -28.00   1.00   0.50    1.92    --    0.00  57.00 -60.00   58
  7  ω    -22.00  21.00   0.50    1.92    --    0.00  46.00 178.00   86
  8  ω     13.00  46.00   0.50    1.92    --    0.00  77.00 -60.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual offset/far'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0010595000
_diffrn_orient_matrix_UB_12      0.0843056000
_diffrn_orient_matrix_UB_13      -0.0047289000
_diffrn_orient_matrix_UB_21      0.0475920000
_diffrn_orient_matrix_UB_22      0.0059610000
_diffrn_orient_matrix_UB_23      0.0187444000
_diffrn_orient_matrix_UB_31      0.0186487000
_diffrn_orient_matrix_UB_32      -0.0103478000
_diffrn_orient_matrix_UB_33      -0.0279223000
_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              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5438
_reflns_number_total             6376
_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       'CrysAlisPro 1.171.43.144a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 39.46e (release 04-06-2018))'
_computing_data_reduction        'CrysAlisPro 1.171.43.144a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.872
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.114
_refine_ls_extinction_coef       0.0046(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         6376
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0381
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0442P)²+0.4278P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.0971
_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,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), N1(H1A,H1B), C4(H4A,H4B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C11(H11), C12(H12), C9(H9), C13(H13), C14(H14), C10(H10), C1(H1),
 C8(H8)
2.c Idealised Me refined as rotating group:
 C2(H2C,H2D,H2E), C5(H5A,H5B,H5C)
;
_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
Fe2 Fe 0.86251(2) 0.76448(3) 0.33728(2) 0.00444(9) Uani 1 1 d . . . . .
Fe3 Fe 0.75007(2) 0.26075(3) 0.50229(2) 0.00366(9) Uani 1 1 d . . . . .
Fe1 Fe 0.64078(2) 0.75363(3) 0.67112(2) 0.00443(9) Uani 1 1 d . . . . .
O11 O 0.86483(9) 0.36902(15) 0.55643(6) 0.0079(2) Uani 1 1 d . . . . .
O13 O 0.83796(9) 0.16434(15) 0.45055(6) 0.0078(2) Uani 1 1 d . . . . .
O17 O 0.63629(9) 0.15007(15) 0.44629(6) 0.0082(2) Uani 1 1 d . . . . .
O15 O 0.77181(9) 0.06304(15) 0.55800(6) 0.0084(3) Uani 1 1 d . . . . .
O3 O 0.72056(9) 1.16969(15) 0.77954(6) 0.0100(3) Uani 1 1 d . . . . .
O7 O 0.72548(9) 0.45454(15) 0.44588(6) 0.0086(3) Uani 1 1 d . . . . .
O6 O 0.66215(9) 0.35159(15) 0.55486(6) 0.0080(2) Uani 1 1 d . . . . .
O12 O 1.01631(9) 0.36582(15) 0.61200(6) 0.0098(3) Uani 1 1 d . . . . .
O10 O 0.76631(9) 0.38698(15) 0.20708(6) 0.0105(3) Uani 1 1 d . . . . .
O2 O 0.57561(9) 0.62898(15) 0.73639(6) 0.0108(3) Uani 1 1 d . . . . .
O4 O 0.63778(9) 0.97199(15) 0.72211(6) 0.0103(3) Uani 1 1 d . . . . .
O9 O 0.84361(9) 0.58534(15) 0.26598(6) 0.0112(3) Uani 1 1 d . . . . .
O1 O 0.45944(9) 0.60994(15) 0.79066(6) 0.0100(3) Uani 1 1 d . . . . .
O5 O 0.61728(9) 0.54464(15) 0.61390(6) 0.0102(3) Uani 1 1 d . . . . .
O14 O 0.89265(9) -0.03801(16) 0.40119(6) 0.0120(3) Uani 1 1 d . . . . .
O8 O 0.76840(9) 0.64804(15) 0.38687(6) 0.0113(3) Uani 1 1 d . . . . .
O18 O 0.49234(9) 0.14698(15) 0.38108(6) 0.0101(3) Uani 1 1 d . . . . .
O16 O 0.72790(9) -0.13472(15) 0.61451(6) 0.0108(3) Uani 1 1 d . . . . .
N2 N 0.55675(12) 0.3155(2) 0.83099(8) 0.0172(4) Uani 1 1 d . . . . .
H2A H 0.535241 0.418496 0.825473 0.021 Uiso 1 1 calc R U . . .
H2B H 0.618154 0.313258 0.824941 0.021 Uiso 1 1 calc R U . . .
N1 N 0.44597(12) 0.1595(2) 0.66529(8) 0.0177(4) Uani 1 1 d . . . . .
H1A H 0.385052 0.140278 0.670380 0.021 Uiso 1 1 calc R U . . .
H1B H 0.478586 0.064660 0.670180 0.021 Uiso 1 1 calc R U . . .
C7 C 0.71412(13) 1.0336(2) 0.75323(8) 0.0093(3) Uani 1 1 d . . . . .
H7 H 0.771710 0.972884 0.757309 0.011 Uiso 1 1 calc R U . . .
C11 C 0.77013(13) 0.5038(2) 0.24503(8) 0.0096(3) Uani 1 1 d . . . . .
H11 H 0.712889 0.531499 0.258601 0.011 Uiso 1 1 calc R U . . .
C12 C 0.83325(13) 0.0219(2) 0.42920(8) 0.0095(3) Uani 1 1 d . . . . .
H12 H 0.780912 -0.043160 0.435001 0.011 Uiso 1 1 calc R U . . .
C9 C 0.94435(12) 0.2986(2) 0.57898(8) 0.0091(3) Uani 1 1 d . . . . .
H9 H 0.949047 0.187478 0.570013 0.011 Uiso 1 1 calc R U . . .
C13 C 0.55730(12) 0.2165(2) 0.42030(8) 0.0083(3) Uani 1 1 d . . . . .
H13 H 0.547037 0.324694 0.431222 0.010 Uiso 1 1 calc R U . . .
C14 C 0.71013(13) -0.0101(2) 0.58202(8) 0.0086(3) Uani 1 1 d . . . . .
H14 H 0.646686 0.032468 0.574847 0.010 Uiso 1 1 calc R U . . .
C10 C 0.78724(13) 0.5277(2) 0.42173(8) 0.0096(3) Uani 1 1 d . . . . .
H10 H 0.851527 0.488469 0.430776 0.012 Uiso 1 1 calc R U . . .
C1 C 0.50669(12) 0.6862(2) 0.75654(8) 0.0095(4) Uani 1 1 d . . . . .
H1 H 0.488515 0.794094 0.745563 0.011 Uiso 1 1 calc R U . . .
C8 C 0.67207(13) 0.4890(2) 0.58125(8) 0.0097(3) Uani 1 1 d . . . . .
H8 H 0.724767 0.553499 0.575661 0.012 Uiso 1 1 calc R U . . .
C2 C 0.55716(16) 0.2637(2) 0.89818(11) 0.0193(4) Uani 1 1 d . . . . .
H2C H 0.582121 0.153883 0.904836 0.029 Uiso 1 1 calc R U . . .
H2D H 0.491320 0.267212 0.905194 0.029 Uiso 1 1 calc R U . . .
H2E H 0.598317 0.336139 0.928424 0.029 Uiso 1 1 calc R U . . .
C4 C 0.49429(15) 0.2740(2) 0.71516(10) 0.0180(4) Uani 1 1 d . . . . .
H4A H 0.460319 0.378505 0.708832 0.022 Uiso 1 1 calc R U . . .
H4B H 0.561406 0.291604 0.710712 0.022 Uiso 1 1 calc R U . . .
C5 C 0.44170(16) 0.2231(2) 0.59926(11) 0.0189(4) Uani 1 1 d . . . . .
H5A H 0.410867 0.143631 0.567594 0.028 Uiso 1 1 calc R U . . .
H5B H 0.507207 0.244510 0.593742 0.028 Uiso 1 1 calc R U . . .
H5C H 0.404253 0.322882 0.593245 0.028 Uiso 1 1 calc R U . . .
C3 C 0.49508(15) 0.2118(2) 0.78229(10) 0.0185(4) Uani 1 1 d . . . . .
H3A H 0.428541 0.210834 0.789370 0.022 Uiso 1 1 calc R U . . .
H3B H 0.519924 0.100411 0.786589 0.022 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
Fe2 O12 2.1236(12) 3_766 ?
Fe2 O10 2.1305(12) 2_655 ?
Fe2 O9 2.1089(12) . ?
Fe2 O1 2.1414(12) 4_675 ?
Fe2 O14 2.1225(12) 1_565 ?
Fe2 O8 2.1150(13) . ?
Fe3 O11 1.9986(12) . ?
Fe3 O13 2.0081(12) . ?
Fe3 O17 2.0146(12) . ?
Fe3 O15 2.0168(12) . ?
Fe3 O7 2.0001(12) . ?
Fe3 O6 2.0028(12) . ?
Fe1 O3 2.1409(12) 2_646 ?
Fe1 O2 2.1092(12) . ?
Fe1 O4 2.1259(12) . ?
Fe1 O5 2.1123(12) . ?
Fe1 O18 2.1433(12) 3_666 ?
Fe1 O16 2.1256(13) 1_565 ?
O11 C9 1.272(2) . ?
O13 C12 1.268(2) . ?
O17 C13 1.267(2) . ?
O15 C14 1.265(2) . ?
O3 C7 1.260(2) . ?
O7 C10 1.268(2) . ?
O6 C8 1.271(2) . ?
O12 C9 1.243(2) . ?
O10 C11 1.261(2) . ?
O2 C1 1.248(2) . ?
O4 C7 1.253(2) . ?
O9 C11 1.245(2) . ?
O1 C1 1.265(2) . ?
O5 C8 1.243(2) . ?
O14 C12 1.241(2) . ?
O8 C10 1.243(2) . ?
O18 C13 1.247(2) . ?
O16 C14 1.244(2) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 C2 1.500(3) . ?
N2 C3 1.484(2) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 C4 1.484(2) . ?
N1 C5 1.498(3) . ?
C7 H7 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C9 H9 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C10 H10 0.9500 . ?
C1 H1 0.9500 . ?
C8 H8 0.9500 . ?
C2 H2C 0.9800 . ?
C2 H2D 0.9800 . ?
C2 H2E 0.9800 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C3 1.525(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C3 H3A 0.9900 . ?
C3 H3B 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
O12 Fe2 O10 174.55(5) 3_766 2_655 ?
O12 Fe2 O1 87.42(5) 3_766 4_675 ?
O10 Fe2 O1 97.84(5) 2_655 4_675 ?
O9 Fe2 O12 88.27(5) . 3_766 ?
O9 Fe2 O10 93.13(5) . 2_655 ?
O9 Fe2 O1 90.12(5) . 4_675 ?
O9 Fe2 O14 172.11(5) . 1_565 ?
O9 Fe2 O8 92.50(5) . . ?
O14 Fe2 O12 92.24(5) 1_565 3_766 ?
O14 Fe2 O10 87.10(5) 1_565 2_655 ?
O14 Fe2 O1 82.04(5) 1_565 4_675 ?
O8 Fe2 O12 92.33(5) . 3_766 ?
O8 Fe2 O10 82.35(5) . 2_655 ?
O8 Fe2 O1 177.36(5) . 4_675 ?
O8 Fe2 O14 95.34(5) . 1_565 ?
O11 Fe3 O13 88.44(5) . . ?
O11 Fe3 O17 178.67(5) . . ?
O11 Fe3 O15 91.43(5) . . ?
O11 Fe3 O7 89.96(5) . . ?
O11 Fe3 O6 91.97(5) . . ?
O13 Fe3 O17 90.25(5) . . ?
O13 Fe3 O15 88.04(5) . . ?
O17 Fe3 O15 88.74(5) . . ?
O7 Fe3 O13 92.18(5) . . ?
O7 Fe3 O17 89.88(5) . . ?
O7 Fe3 O15 178.60(5) . . ?
O7 Fe3 O6 89.18(5) . . ?
O6 Fe3 O13 178.59(5) . . ?
O6 Fe3 O17 89.35(5) . . ?
O6 Fe3 O15 90.60(5) . . ?
O3 Fe1 O18 175.48(5) 2_646 3_666 ?
O2 Fe1 O3 90.14(5) . 2_646 ?
O2 Fe1 O4 91.17(5) . . ?
O2 Fe1 O5 86.64(5) . . ?
O2 Fe1 O18 94.02(5) . 3_666 ?
O2 Fe1 O16 170.69(5) . 1_565 ?
O4 Fe1 O3 98.35(5) . 2_646 ?
O4 Fe1 O18 79.82(5) . 3_666 ?
O5 Fe1 O3 91.68(5) . 2_646 ?
O5 Fe1 O4 169.74(5) . . ?
O5 Fe1 O18 90.33(5) . 3_666 ?
O5 Fe1 O16 93.92(5) . 1_565 ?
O16 Fe1 O3 80.56(5) 1_565 2_646 ?
O16 Fe1 O4 89.86(5) 1_565 . ?
O16 Fe1 O18 95.27(5) 1_565 3_666 ?
C9 O11 Fe3 123.90(12) . . ?
C12 O13 Fe3 125.62(12) . . ?
C13 O17 Fe3 125.57(12) . . ?
C14 O15 Fe3 127.07(12) . . ?
C7 O3 Fe1 118.94(11) . 2_656 ?
C10 O7 Fe3 126.05(12) . . ?
C8 O6 Fe3 124.57(12) . . ?
C9 O12 Fe2 122.42(12) . 3_766 ?
C11 O10 Fe2 124.68(12) . 2_645 ?
C1 O2 Fe1 122.12(12) . . ?
C7 O4 Fe1 120.76(12) . . ?
C11 O9 Fe2 127.70(12) . . ?
C1 O1 Fe2 119.97(11) . 4_576 ?
C8 O5 Fe1 126.39(12) . . ?
C12 O14 Fe2 124.01(12) . 1_545 ?
C10 O8 Fe2 126.39(12) . . ?
C13 O18 Fe1 127.73(12) . 3_666 ?
C14 O16 Fe1 127.64(12) . 1_545 ?
H2A N2 H2B 107.8 . . ?
C2 N2 H2A 109.1 . . ?
C2 N2 H2B 109.1 . . ?
C3 N2 H2A 109.1 . . ?
C3 N2 H2B 109.1 . . ?
C3 N2 C2 112.63(16) . . ?
H1A N1 H1B 108.0 . . ?
C4 N1 H1A 109.3 . . ?
C4 N1 H1B 109.3 . . ?
C4 N1 C5 111.60(16) . . ?
C5 N1 H1A 109.3 . . ?
C5 N1 H1B 109.3 . . ?
O3 C7 H7 117.4 . . ?
O4 C7 O3 125.19(17) . . ?
O4 C7 H7 117.4 . . ?
O10 C11 H11 117.7 . . ?
O9 C11 O10 124.63(17) . . ?
O9 C11 H11 117.7 . . ?
O13 C12 H12 117.9 . . ?
O14 C12 O13 124.18(17) . . ?
O14 C12 H12 117.9 . . ?
O11 C9 H9 117.9 . . ?
O12 C9 O11 124.14(18) . . ?
O12 C9 H9 117.9 . . ?
O17 C13 H13 118.4 . . ?
O18 C13 O17 123.27(17) . . ?
O18 C13 H13 118.4 . . ?
O15 C14 H14 118.2 . . ?
O16 C14 O15 123.67(17) . . ?
O16 C14 H14 118.2 . . ?
O7 C10 H10 118.2 . . ?
O8 C10 O7 123.66(17) . . ?
O8 C10 H10 118.2 . . ?
O2 C1 O1 124.25(17) . . ?
O2 C1 H1 117.9 . . ?
O1 C1 H1 117.9 . . ?
O6 C8 H8 117.9 . . ?
O5 C8 O6 124.25(17) . . ?
O5 C8 H8 117.9 . . ?
N2 C2 H2C 109.5 . . ?
N2 C2 H2D 109.5 . . ?
N2 C2 H2E 109.5 . . ?
H2C C2 H2D 109.5 . . ?
H2C C2 H2E 109.5 . . ?
H2D C2 H2E 109.5 . . ?
N1 C4 H4A 109.3 . . ?
N1 C4 H4B 109.3 . . ?
N1 C4 C3 111.49(17) . . ?
H4A C4 H4B 108.0 . . ?
C3 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C3 C4 110.26(17) . . ?
N2 C3 H3A 109.6 . . ?
N2 C3 H3B 109.6 . . ?
C4 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2A O1 0.91 1.98 2.855(2) 161.7 . yes
N2 H2B O3 0.91 2.26 3.037(2) 143.1 1_545 yes
N2 H2B O16 0.91 2.33 3.058(2) 137.0 2_656 yes
N1 H1A O10 0.91 2.02 2.909(2) 164.1 4_566 yes
N1 H1B O4 0.91 2.42 3.148(2) 137.0 1_545 yes
N1 H1B O18 0.91 2.16 2.940(2) 142.9 3_656 yes
C7 H7 O3 0.95 2.65 3.290(2) 124.7 2_646 yes
C9 H9 O14 0.95 2.53 3.135(2) 121.9 3_756 yes
C10 H10 O12 0.95 2.57 3.159(2) 120.7 3_766 yes
C1 H1 O9 0.95 2.42 3.039(2) 123.0 4_576 yes
C2 H2D O14 0.98 2.65 3.280(2) 122.5 4_566 yes
C5 H5C O8 0.98 2.59 3.247(3) 124.4 3_666 yes

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
Fe2 O12 C9 O11 168.24(13) 3_766 . . . ?
Fe2 O10 C11 O9 -172.56(13) 2_645 . . . ?
Fe2 O9 C11 O10 -172.31(12) . . . . ?
Fe2 O1 C1 O2 167.70(13) 4_576 . . . ?
Fe2 O14 C12 O13 -156.87(13) 1_545 . . . ?
Fe2 O8 C10 O7 -173.65(12) . . . . ?
Fe3 O11 C9 O12 179.06(13) . . . . ?
Fe3 O13 C12 O14 -174.71(12) . . . . ?
Fe3 O17 C13 O18 172.86(12) . . . . ?
Fe3 O15 C14 O16 177.76(12) . . . . ?
Fe3 O7 C10 O8 -179.99(12) . . . . ?
Fe3 O6 C8 O5 -179.90(12) . . . . ?
Fe1 O3 C7 O4 -178.76(13) 2_656 . . . ?
Fe1 O2 C1 O1 172.82(12) . . . . ?
Fe1 O4 C7 O3 172.61(13) . . . . ?
Fe1 O5 C8 O6 169.50(12) . . . . ?
Fe1 O18 C13 O17 -175.91(12) 3_666 . . . ?
Fe1 O16 C14 O15 168.12(12) 1_545 . . . ?
N1 C4 C3 N2 171.13(14) . . . . ?
C2 N2 C3 C4 177.74(17) . . . . ?
C5 N1 C4 C3 177.80(17) . . . . ?

_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 2.666
_oxdiff_exptl_absorpt_empirical_full_min 0.574
####################################################################### 
# 
# 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_3LTP
_database_code_depnum_ccdc_archive 'CCDC 2470386'
loop_
_audit_author_name
_audit_author_address
'Jiong-Peng Zhao'
;Tianjin University Of Technology
China
;
_audit_update_record             
;
2025-07-07 deposited with the CCDC.	2025-09-15 downloaded from the CCDC.
;
_audit_creation_date             2025-06-05
_audit_creation_method           
;
Olex2 1.5-ac6-020
(compiled 2024.02.14 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6966)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H9 Fe3 O18, C6 H18 N2'
_chemical_formula_sum            'C15 H27 Fe3 N2 O18'
_chemical_formula_weight         690.93
_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'
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      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                   14.3325(10)
_cell_length_b                   8.4968(6)
_cell_length_c                   21.8494(14)
_cell_angle_alpha                90
_cell_angle_beta                 102.465(7)
_cell_angle_gamma                90
_cell_volume                     2598.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4056
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      33.1260
_cell_measurement_theta_min      2.9770
_shelx_estimated_absorpt_T_max   0.757
_shelx_estimated_absorpt_T_min   0.624
_exptl_absorpt_coefficient_mu    1.737
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59481
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.766
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1412
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0789
_diffrn_reflns_av_unetI/netI     0.0940
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10256
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.505
_diffrn_reflns_theta_min         1.905
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00 109.00   1.00   12.00    --   30.00  54.00 240.00  174
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0115091000
_diffrn_orient_matrix_UB_12      -0.0800957000
_diffrn_orient_matrix_UB_13      0.0067998000
_diffrn_orient_matrix_UB_21      -0.0483188000
_diffrn_orient_matrix_UB_22      -0.0155342000
_diffrn_orient_matrix_UB_23      0.0009815000
_diffrn_orient_matrix_UB_31      -0.0101939000
_diffrn_orient_matrix_UB_32      -0.0172261000
_diffrn_orient_matrix_UB_33      -0.0325449000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4225
_reflns_number_total             7353
_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       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.620
_refine_diff_density_min         -2.127
_refine_diff_density_rms         0.172
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         7353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1214
_refine_ls_R_factor_gt           0.0652
_refine_ls_restrained_S_all      1.053
_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)+(0.0912P)²+5.0345P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1634
_refine_ls_wR_factor_ref         0.2400
_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,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B), C14(H14A,H14B), C13(H13A,H13B), C11(H11A,H11B),
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C8(H8), C7(H7), C6(H6), C2(H2), C5(H5), C4(H4), C1(H1)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C10(H10A,H10B,H10C)
;
_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
Fe3 Fe 0.25004(4) 0.22553(8) 0.50005(3) 0.01349(17) Uani 1 1 d . . . . .
Fe2 Fe 0.14276(4) 0.72704(8) 0.67187(3) 0.01551(18) Uani 1 1 d . . . . .
Fe1 Fe 0.63966(5) 0.27556(8) 0.66415(3) 0.01564(18) Uani 1 1 d . . . . .
O18 O 0.3709(2) 0.1318(4) 0.55192(16) 0.0259(8) Uani 1 1 d . . . . .
O14 O 0.3349(3) 0.3271(4) 0.44812(16) 0.0270(8) Uani 1 1 d . . . . .
O16 O 0.1354(3) 0.3321(4) 0.44516(18) 0.0311(9) Uani 1 1 d . . . . .
O12 O 0.1671(3) 0.1204(4) 0.55244(17) 0.0273(8) Uani 1 1 d . . . . .
O15 O -0.0059(2) 0.3644(4) 0.38012(17) 0.0282(8) Uani 1 1 d . . . . .
O6 O 0.4284(3) 0.3561(4) 0.76764(18) 0.0305(8) Uani 1 1 d . . . . .
O5 O 0.5390(3) 0.3871(4) 0.71106(16) 0.0293(8) Uani 1 1 d . . . . .
O10 O 0.2269(3) 0.0337(4) 0.44423(18) 0.0309(9) Uani 1 1 d . . . . .
O11 O 0.1247(3) -0.0687(4) 0.61251(17) 0.0294(8) Uani 1 1 d . . . . .
O17 O 0.5200(3) 0.1538(4) 0.60750(17) 0.0301(8) Uani 1 1 d . . . . .
O13 O 0.3859(3) 0.5210(5) 0.39483(17) 0.0304(9) Uani 1 1 d . . . . .
O9 O 0.2639(3) -0.1631(4) 0.38624(17) 0.0312(9) Uani 1 1 d . . . . .
O8 O 0.6572(3) 0.0853(4) 0.72876(18) 0.0328(9) Uani 1 1 d . . . . .
O1 O 0.2653(3) 0.4161(4) 0.55629(17) 0.0312(8) Uani 1 1 d . . . . .
O2 O 0.2277(3) 0.6049(4) 0.61720(18) 0.0360(9) Uani 1 1 d . . . . .
O4 O 0.2195(3) 0.3172(4) 0.78040(18) 0.0306(9) Uani 1 1 d . . . . .
O7 O 0.7327(3) -0.1086(4) 0.78819(18) 0.0319(9) Uani 1 1 d . . . . .
O3 O 0.1402(3) 0.5162(5) 0.72473(19) 0.0340(9) Uani 1 1 d . . . . .
C3 C 0.4941(3) 0.3061(6) 0.7424(2) 0.0269(11) Uani 1 1 d . . . . .
H3 H 0.510239 0.200180 0.747654 0.032 Uiso 1 1 calc R U . . .
N1 N 0.4603(3) 0.7041(6) 0.6746(3) 0.0408(13) Uani 1 1 d . . . . .
H1A H 0.479556 0.604608 0.674092 0.049 Uiso 1 1 calc R U . . .
H1B H 0.398789 0.703664 0.676068 0.049 Uiso 1 1 calc R U . . .
C9 C 0.4443(3) 0.2091(6) 0.5769(2) 0.0251(11) Uani 1 1 d . . . . .
H9 H 0.441356 0.317756 0.571870 0.030 Uiso 1 1 calc R U . . .
C8 C 0.0572(3) 0.2829(6) 0.4135(2) 0.0253(11) Uani 1 1 d . . . . .
H8 H 0.045276 0.175558 0.415255 0.030 Uiso 1 1 calc R U . . .
C7 C 0.3285(4) 0.4630(6) 0.4232(2) 0.0273(11) Uani 1 1 d . . . . .
H7 H 0.276073 0.524090 0.426737 0.033 Uiso 1 1 calc R U . . .
C6 C 0.1807(4) -0.0061(6) 0.5843(3) 0.0298(11) Uani 1 1 d . . . . .
H6 H 0.238917 -0.056509 0.586615 0.036 Uiso 1 1 calc R U . . .
N2 N 0.5514(4) 0.7968(6) 0.8484(3) 0.0451(14) Uani 1 1 d . . . . .
H2A H 0.526447 0.892973 0.847101 0.054 Uiso 1 1 calc R U . . .
H2B H 0.613175 0.806821 0.848278 0.054 Uiso 1 1 calc R U . . .
C2 C 0.2158(4) 0.4486(6) 0.7528(2) 0.0287(11) Uani 1 1 d . . . . .
H2 H 0.273392 0.499611 0.753238 0.034 Uiso 1 1 calc R U . . .
C5 C 0.2835(4) -0.0412(6) 0.4190(2) 0.0317(12) Uani 1 1 d . . . . .
H5 H 0.345663 -0.003269 0.424947 0.038 Uiso 1 1 calc R U . . .
C4 C 0.7304(4) 0.0094(6) 0.7529(2) 0.0301(12) Uani 1 1 d . . . . .
H4 H 0.787918 0.042424 0.744089 0.036 Uiso 1 1 calc R U . . .
C1 C 0.2115(4) 0.4819(6) 0.5864(2) 0.0308(12) Uani 1 1 d . . . . .
H1 H 0.153085 0.433487 0.585531 0.037 Uiso 1 1 calc R U . . .
C14 C 0.5417(5) 0.7183(8) 0.9081(4) 0.058(2) Uani 1 1 d . . . . .
H14A H 0.474193 0.706360 0.907425 0.070 Uiso 1 1 calc R U . . .
H14B H 0.568805 0.613505 0.908929 0.070 Uiso 1 1 calc R U . . .
C15 C 0.5874(6) 0.7999(9) 0.9673(4) 0.061(2) Uani 1 1 d . . . . .
H15A H 0.559614 0.902421 0.968220 0.092 Uiso 1 1 calc R U . . .
H15B H 0.654723 0.810131 0.969485 0.092 Uiso 1 1 calc R U . . .
H15C H 0.577284 0.739602 1.002515 0.092 Uiso 1 1 calc R U . . .
C13 C 0.5041(5) 0.7097(8) 0.7922(4) 0.0529(19) Uani 1 1 d . . . . .
H13A H 0.436346 0.702294 0.791671 0.064 Uiso 1 1 calc R U . . .
H13B H 0.529496 0.603521 0.794596 0.064 Uiso 1 1 calc R U . . .
C11 C 0.4719(6) 0.7832(8) 0.6164(4) 0.060(2) Uani 1 1 d . . . . .
H11A H 0.539311 0.784263 0.615647 0.072 Uiso 1 1 calc R U . . .
H11B H 0.451481 0.891748 0.617750 0.072 Uiso 1 1 calc R U . . .
C10 C 0.4180(6) 0.7106(9) 0.5562(4) 0.065(2) Uani 1 1 d . . . . .
H10A H 0.427862 0.772269 0.521376 0.098 Uiso 1 1 calc R U . . .
H10B H 0.351031 0.707920 0.556324 0.098 Uiso 1 1 calc R U . . .
H10C H 0.440617 0.605411 0.552690 0.098 Uiso 1 1 calc R U . . .
C12 C 0.5165(5) 0.7842(8) 0.7317(4) 0.0523(19) Uani 1 1 d . . . . .
H12A H 0.496921 0.893557 0.731209 0.063 Uiso 1 1 calc R U . . .
H12B H 0.583656 0.781942 0.730375 0.063 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
Fe3 O18 2.018(3) . ?
Fe3 O14 2.027(3) . ?
Fe3 O16 2.027(3) . ?
Fe3 O12 2.027(3) . ?
Fe3 O10 2.020(3) . ?
Fe3 O1 2.016(4) . ?
Fe2 O15 2.186(3) 3_566 ?
Fe2 O6 2.139(4) 2_556 ?
Fe2 O11 2.149(4) 1_565 ?
Fe2 O2 2.148(4) . ?
Fe2 O4 2.163(4) 2_556 ?
Fe2 O3 2.136(4) . ?
Fe1 O5 2.160(4) . ?
Fe1 O17 2.151(3) . ?
Fe1 O13 2.140(4) 3_666 ?
Fe1 O9 2.166(4) 3_656 ?
Fe1 O8 2.125(4) . ?
Fe1 O7 2.140(4) 2_656 ?
O18 C9 1.260(6) . ?
O14 C7 1.271(6) . ?
O16 C8 1.255(6) . ?
O12 C6 1.273(6) . ?
O15 C8 1.243(6) . ?
O6 C3 1.264(6) . ?
O5 C3 1.243(6) . ?
O10 C5 1.250(7) . ?
O11 C6 1.232(6) . ?
O17 C9 1.238(6) . ?
O13 C7 1.234(6) . ?
O9 C5 1.255(6) . ?
O8 C4 1.247(6) . ?
O1 C1 1.248(6) . ?
O2 C1 1.238(6) . ?
O4 C2 1.265(6) . ?
O7 C4 1.261(6) . ?
O3 C2 1.262(6) . ?
C3 H3 0.9300 . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 C11 1.478(9) . ?
N1 C12 1.496(9) . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?
C7 H7 0.9300 . ?
C6 H6 0.9300 . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 C14 1.498(9) . ?
N2 C13 1.469(9) . ?
C2 H2 0.9300 . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C1 H1 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.489(10) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C12 1.510(11) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C10 1.505(12) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C12 H12A 0.9700 . ?
C12 H12B 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
O18 Fe3 O14 86.34(15) . . ?
O18 Fe3 O16 175.35(15) . . ?
O18 Fe3 O12 92.65(15) . . ?
O18 Fe3 O10 91.73(15) . . ?
O14 Fe3 O16 89.21(16) . . ?
O14 Fe3 O12 178.86(14) . . ?
O12 Fe3 O16 91.82(16) . . ?
O10 Fe3 O14 92.63(15) . . ?
O10 Fe3 O16 89.81(15) . . ?
O10 Fe3 O12 86.88(16) . . ?
O1 Fe3 O18 90.43(15) . . ?
O1 Fe3 O14 90.00(16) . . ?
O1 Fe3 O16 88.23(15) . . ?
O1 Fe3 O12 90.54(16) . . ?
O1 Fe3 O10 176.70(15) . . ?
O6 Fe2 O15 90.52(15) 2_556 3_566 ?
O6 Fe2 O11 86.99(15) 2_556 1_565 ?
O6 Fe2 O2 174.16(15) 2_556 . ?
O6 Fe2 O4 91.59(15) 2_556 2_556 ?
O11 Fe2 O15 89.78(14) 1_565 3_566 ?
O11 Fe2 O4 89.05(15) 1_565 2_556 ?
O2 Fe2 O15 95.29(15) . 3_566 ?
O2 Fe2 O11 93.63(15) . 1_565 ?
O2 Fe2 O4 82.61(15) . 2_556 ?
O4 Fe2 O15 177.52(15) 2_556 3_566 ?
O3 Fe2 O15 82.22(14) . 3_566 ?
O3 Fe2 O6 91.71(15) . 2_556 ?
O3 Fe2 O11 171.88(14) . 1_565 ?
O3 Fe2 O2 88.49(16) . . ?
O3 Fe2 O4 99.01(15) . 2_556 ?
O5 Fe1 O9 177.71(14) . 3_656 ?
O17 Fe1 O5 87.32(15) . . ?
O17 Fe1 O9 90.69(15) . 3_656 ?
O13 Fe1 O5 83.48(14) 3_666 . ?
O13 Fe1 O17 91.76(14) 3_666 . ?
O13 Fe1 O9 95.47(14) 3_666 3_656 ?
O8 Fe1 O5 90.80(14) . . ?
O8 Fe1 O17 88.95(14) . . ?
O8 Fe1 O13 174.19(15) . 3_666 ?
O8 Fe1 O9 90.29(15) . 3_656 ?
O8 Fe1 O7 93.47(15) . 2_656 ?
O7 Fe1 O5 98.95(15) 2_656 . ?
O7 Fe1 O17 173.24(15) 2_656 . ?
O7 Fe1 O13 86.47(15) 2_656 3_666 ?
O7 Fe1 O9 83.00(14) 2_656 3_656 ?
C9 O18 Fe3 125.0(3) . . ?
C7 O14 Fe3 129.0(4) . . ?
C8 O16 Fe3 133.7(3) . . ?
C6 O12 Fe3 130.0(4) . . ?
C8 O15 Fe2 124.3(3) . 3_566 ?
C3 O6 Fe2 126.7(3) . 2_546 ?
C3 O5 Fe1 119.7(3) . . ?
C5 O10 Fe3 129.8(4) . . ?
C6 O11 Fe2 130.1(4) . 1_545 ?
C9 O17 Fe1 128.7(3) . . ?
C7 O13 Fe1 125.4(4) . 3_666 ?
C5 O9 Fe1 124.4(4) . 3_656 ?
C4 O8 Fe1 130.0(4) . . ?
C1 O1 Fe3 133.1(4) . . ?
C1 O2 Fe2 130.4(4) . . ?
C2 O4 Fe2 118.8(3) . 2_546 ?
C4 O7 Fe1 124.8(3) . 2_646 ?
C2 O3 Fe2 122.1(3) . . ?
O6 C3 H3 117.4 . . ?
O5 C3 O6 125.2(5) . . ?
O5 C3 H3 117.4 . . ?
H1A N1 H1B 107.9 . . ?
C11 N1 H1A 109.3 . . ?
C11 N1 H1B 109.3 . . ?
C11 N1 C12 111.8(5) . . ?
C12 N1 H1A 109.3 . . ?
C12 N1 H1B 109.3 . . ?
O18 C9 H9 117.0 . . ?
O17 C9 O18 126.1(5) . . ?
O17 C9 H9 117.0 . . ?
O16 C8 H8 117.0 . . ?
O15 C8 O16 126.0(5) . . ?
O15 C8 H8 117.0 . . ?
O14 C7 H7 117.2 . . ?
O13 C7 O14 125.7(5) . . ?
O13 C7 H7 117.2 . . ?
O12 C6 H6 116.6 . . ?
O11 C6 O12 126.8(5) . . ?
O11 C6 H6 116.6 . . ?
H2A N2 H2B 107.8 . . ?
C14 N2 H2A 109.0 . . ?
C14 N2 H2B 109.0 . . ?
C13 N2 H2A 109.0 . . ?
C13 N2 H2B 109.0 . . ?
C13 N2 C14 113.0(5) . . ?
O4 C2 H2 117.4 . . ?
O3 C2 O4 125.2(5) . . ?
O3 C2 H2 117.4 . . ?
O10 C5 O9 125.8(6) . . ?
O10 C5 H5 117.1 . . ?
O9 C5 H5 117.1 . . ?
O8 C4 O7 125.4(5) . . ?
O8 C4 H4 117.3 . . ?
O7 C4 H4 117.3 . . ?
O1 C1 H1 116.5 . . ?
O2 C1 O1 126.9(6) . . ?
O2 C1 H1 116.5 . . ?
N2 C14 H14A 108.2 . . ?
N2 C14 H14B 108.2 . . ?
H14A C14 H14B 107.4 . . ?
C15 C14 N2 116.3(6) . . ?
C15 C14 H14A 108.2 . . ?
C15 C14 H14B 108.2 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C13 H13A 108.8 . . ?
N2 C13 H13B 108.8 . . ?
N2 C13 C12 113.6(5) . . ?
H13A C13 H13B 107.7 . . ?
C12 C13 H13A 108.8 . . ?
C12 C13 H13B 108.8 . . ?
N1 C11 H11A 108.4 . . ?
N1 C11 H11B 108.4 . . ?
N1 C11 C10 115.6(6) . . ?
H11A C11 H11B 107.4 . . ?
C10 C11 H11A 108.4 . . ?
C10 C11 H11B 108.4 . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C11 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C12 C13 113.4(5) . . ?
N1 C12 H12A 108.9 . . ?
N1 C12 H12B 108.9 . . ?
C13 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C3 H3 O8 0.93 2.44 3.061(6) 124.5 . yes
N1 H1A O5 0.89 2.12 2.962(6) 157.4 . yes
N1 H1B O4 0.89 2.33 3.104(6) 146.1 2_556 yes
C8 H8 O11 0.93 2.55 3.129(6) 120.9 3_556 yes
N2 H2A O15 0.89 2.26 3.112(6) 159.0 4_676 yes
N2 H2B O9 0.89 2.46 3.188(7) 138.7 4_666 yes
N2 H2B O7 0.89 2.48 3.257(6) 146.2 1_565 yes
C2 H2 O6 0.93 2.49 3.095(6) 122.5 . yes
C5 H5 O17 0.93 2.54 3.144(7) 123.2 3_656 yes
C15 H15A O16 0.96 2.60 3.260(8) 126.3 4_676 yes
C13 H13B O6 0.97 2.55 3.199(7) 124.5 . yes
C11 H11B O17 0.97 2.46 3.238(8) 136.7 1_565 yes
C12 H12A O3 0.97 2.59 3.279(8) 128.5 2_556 yes
C12 H12B O7 0.97 2.42 3.210(7) 138.3 1_565 yes

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
Fe3 O18 C9 O17 -178.0(4) . . . . ?
Fe3 O14 C7 O13 175.9(4) . . . . ?
Fe3 O16 C8 O15 -177.6(4) . . . . ?
Fe3 O12 C6 O11 -175.6(4) . . . . ?
Fe3 O10 C5 O9 177.6(4) . . . . ?
Fe3 O1 C1 O2 -176.0(4) . . . . ?
Fe2 O15 C8 O16 -178.1(4) 3_566 . . . ?
Fe2 O6 C3 O5 -174.5(4) 2_546 . . . ?
Fe2 O11 C6 O12 -176.0(4) 1_545 . . . ?
Fe2 O2 C1 O1 -178.8(4) . . . . ?
Fe2 O4 C2 O3 -178.0(4) 2_546 . . . ?
Fe2 O3 C2 O4 -173.7(4) . . . . ?
Fe1 O5 C3 O6 -174.1(4) . . . . ?
Fe1 O17 C9 O18 -168.9(4) . . . . ?
Fe1 O13 C7 O14 165.4(4) 3_666 . . . ?
Fe1 O9 C5 O10 173.6(4) 3_656 . . . ?
Fe1 O8 C4 O7 -175.5(4) . . . . ?
Fe1 O7 C4 O8 -174.1(4) 2_646 . . . ?
N2 C13 C12 N1 -174.4(5) . . . . ?
C14 N2 C13 C12 -177.8(6) . . . . ?
C13 N2 C14 C15 -179.7(7) . . . . ?
C11 N1 C12 C13 178.2(6) . . . . ?
C12 N1 C11 C10 179.9(7) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.319
_oxdiff_exptl_absorpt_empirical_full_min 0.761
####################################################################### 
# 
# 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_1HTP
_database_code_depnum_ccdc_archive 'CCDC 2470383'
loop_
_audit_author_name
_audit_author_address
'Jiong-Peng Zhao'
;Tianjin University Of Technology
China
;
_audit_update_record             
;
2025-07-07 deposited with the CCDC.	2025-09-15 downloaded from the CCDC.
;
_audit_creation_date             2025-06-02
_audit_creation_method           
;
Olex2 1.5-ac6-020
(compiled 2024.02.14 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6966)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H9 Fe3 O18, C3 H12 N2, H2 O'
_chemical_formula_sum            'C12 H23 Fe3 N2 O19'
_chemical_formula_weight         666.87
_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'
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      trigonal
_space_group_IT_number           167
_space_group_name_H-M_alt        'R -3 c'
_space_group_name_Hall           '-R 3 2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+5/6'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+7/6'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z-1/6'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+1/6'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'

_cell_length_a                   8.2548(6)
_cell_length_b                   8.2548(6)
_cell_length_c                   63.391(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3740.9(6)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    1932
_cell_measurement_temperature    403.00(10)
_cell_measurement_theta_max      29.8670
_cell_measurement_theta_min      5.2770
_shelx_estimated_absorpt_T_max   0.840
_shelx_estimated_absorpt_T_min   0.714
_exptl_absorpt_coefficient_mu    1.809
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.776
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2034
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0778
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       84
_diffrn_reflns_limit_l_min       -78
_diffrn_reflns_number            5423
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.822
_diffrn_reflns_theta_min         3.839
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      403.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  28.00   0.50    4.16    --    0.00 -57.00 150.00  108
  2  ω    -87.00 -20.00   0.50    4.16    --    0.00 -77.00 -60.00  134
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual offset/far'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0325806000
_diffrn_orient_matrix_UB_12      0.0715563000
_diffrn_orient_matrix_UB_13      -0.0077322000
_diffrn_orient_matrix_UB_21      -0.0548312000
_diffrn_orient_matrix_UB_22      0.0348394000
_diffrn_orient_matrix_UB_23      0.0046094000
_diffrn_orient_matrix_UB_31      0.0760214000
_diffrn_orient_matrix_UB_32      0.0591646000
_diffrn_orient_matrix_UB_33      0.0066493000
_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              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                848
_reflns_number_total             1124
_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       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    
'olex2.solve 1.5-ac6-020 (Bourhis et al., 2015)'
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1124
_refine_ls_number_restraints     112
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0346
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0401P)²+4.4057P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.1023
_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,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 N1-C1 = N2-C3 = N2-C2 = C1-C2
 1.48 with sigma of 0.02
 N2-C1
 2.5 with sigma of 0.02
 N2-C3 = N2-C2 = C1-C2 = N1-C1
 1.48 with sigma of 0.02
3. Rigid bond restraints
 N1, C3, O1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C1, N1, C2, N2, C3, O1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C3 \\sim N1 \\sim O1: within 3.8A with sigma of 0.01 and sigma for terminal
atoms of 0.03 within 3.8A
N1 \\sim C1 \\sim C2 \\sim N2 \\sim C3 \\sim O1: within 3.8A with sigma of 0.01
and sigma for terminal atoms of 0.03 within 3.8A
Uanis(N1) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(N2) \\sim
Ueq, Uanis(C3) \\sim Ueq, Uanis(O1) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.2
5. Others
 Fixed Sof: N1(0.166667) H1A(0.166667) H1C(0.166667) H1B(0.166667)
 C3(0.166667) H3A(0.166667) H3B(0.166667) H3C(0.166667) O1(0.166667)
 H1F(0.166667) H1G(0.166667) C2(0.166667) H2A(0.166667) H2B(0.166667)
 N2(0.166667) H2D(0.166667) H2C(0.166667) C1(0.166667) H1D(0.166667)
 H1E(0.166667)
6.a Riding coordinates:
 N1(H1A,H1C,H1B), C3(H3A,H3B,H3C), O1(H1F,H1G), N2(H2D,H2C), C1(H1D,H1E)
6.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
6.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_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
Fe2 Fe 0.666667 0.333333 0.333333 0.0211(2) Uani 1 6 d S T P . .
Fe1 Fe 0.333333 0.666667 0.27812(2) 0.02448(19) Uani 1 3 d S T P . .
O4 O 0.6763(2) 0.5383(2) 0.31538(2) 0.0382(4) Uani 1 1 d . . . . .
O3 O 0.5532(2) 0.6725(2) 0.29646(3) 0.0478(4) Uani 1 1 d . . . . .
O2 O 0.3173(3) 0.4448(3) 0.25982(3) 0.0590(5) Uani 1 1 d . . . . .
C4 C 0.5423(3) 0.5452(4) 0.30727(3) 0.0406(5) Uani 1 1 d . . . . .
H4 H 0.423318 0.444149 0.309678 0.049 Uiso 1 1 calc R U . . .
C5 C 0.4471(4) 0.4471(4) 0.250000 0.0446(7) Uani 1 2 d S T P . .
H5 H 0.559775 0.559775 0.250000 0.054 Uiso 1 2 calc R U P . .
N1 N 0.071(3) 0.117(3) 0.2201(3) 0.070(5) Uani 0.1667 1 d D U P A -1
H1A H 0.045328 0.080325 0.206731 0.084 Uiso 0.1667 1 d R U P A -1
H1C H 0.043808 0.207055 0.222551 0.084 Uiso 0.1667 1 d R U P A -1
H1B H 0.192298 0.161015 0.222551 0.084 Uiso 0.1667 1 d R U P A -1
C3 C -0.012(7) -0.049(4) 0.2955(3) 0.081(8) Uani 0.1667 1 d D U P A -1
H3A H 0.033014 0.083090 0.296721 0.121 Uiso 0.1667 1 d R U P A -1
H3B H 0.087744 -0.072760 0.298761 0.121 Uiso 0.1667 1 d R U P A -1
H3C H -0.113256 -0.115660 0.305201 0.121 Uiso 0.1667 1 d R U P A -1
O1 O -0.013(8) -0.068(3) 0.1876(3) 0.144(13) Uani 0.1667 1 d . U P B -1
H1F H -0.099068 -0.166428 0.191969 0.216 Uiso 0.1667 1 d R U P B -1
H1G H 0.063692 -0.089228 0.187249 0.216 Uiso 0.1667 1 d R U P B -1
C2 C 0.015(9) 0.031(4) 0.2569(2) 0.074(5) Uani 0.1667 1 d D U P A -1
H2A H 0.148689 0.081339 0.258152 0.089 Uiso 0.1667 1 calc R U P A -1
H2B H -0.008970 0.133466 0.259372 0.089 Uiso 0.1667 1 calc R U P A -1
N2 N -0.078(3) -0.108(3) 0.2736(3) 0.069(5) Uani 0.1667 1 d D U P A -1
H2D H -0.076935 -0.213697 0.271205 0.083 Uiso 0.1667 1 d R U P A -1
H2C H -0.195915 -0.133677 0.272655 0.083 Uiso 0.1667 1 d R U P A -1
C1 C -0.042(4) -0.037(4) 0.2349(2) 0.070(5) Uani 0.1667 1 d D U P A -1
H1D H -0.026496 -0.139388 0.229944 0.084 Uiso 0.1667 1 d R U P A -1
H1E H -0.173036 -0.074658 0.232824 0.084 Uiso 0.1667 1 d R 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
Fe2 O4 2.0072(14) 3_665 ?
Fe2 O4 2.0074(14) 31_655 ?
Fe2 O4 2.0074(14) . ?
Fe2 O4 2.0074(14) 33_545 ?
Fe2 O4 2.0074(14) 32 ?
Fe2 O4 2.0072(14) 2_655 ?
Fe1 O3 2.1355(14) . ?
Fe1 O3 2.1356(14) 2_665 ?
Fe1 O3 2.1355(15) 3_565 ?
Fe1 O2 2.1154(15) 3_565 ?
Fe1 O2 2.1154(15) . ?
Fe1 O2 2.1154(16) 2_665 ?
O4 C4 1.247(3) . ?
O3 C4 1.219(2) . ?
O2 C5 1.231(2) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
N1 H1A 0.8898 . ?
N1 H1C 0.8903 . ?
N1 H1B 0.8902 . ?
N1 C1 1.478(14) . ?
C3 H3A 0.9601 . ?
C3 H3B 0.9601 . ?
C3 H3C 0.9606 . ?
C3 N2 1.485(13) . ?
O1 H1F 0.8126 . ?
O1 H1G 0.7383 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 N2 1.461(14) . ?
C2 C1 1.492(13) . ?
N2 H2D 0.8899 . ?
N2 H2C 0.8899 . ?
C1 H1D 0.9698 . ?
C1 H1E 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
O4 Fe2 O4 91.04(6) 3_665 2_655 ?
O4 Fe2 O4 88.97(6) 2_655 31_655 ?
O4 Fe2 O4 88.97(6) 3_665 32 ?
O4 Fe2 O4 88.97(6) . 32 ?
O4 Fe2 O4 180.0 . 31_655 ?
O4 Fe2 O4 88.98(6) . 33_545 ?
O4 Fe2 O4 88.97(6) 3_665 31_655 ?
O4 Fe2 O4 91.03(6) 3_665 . ?
O4 Fe2 O4 88.97(6) 2_655 33_545 ?
O4 Fe2 O4 180.0 3_665 33_545 ?
O4 Fe2 O4 91.02(6) 31_655 33_545 ?
O4 Fe2 O4 91.03(6) 2_655 . ?
O4 Fe2 O4 91.03(6) 32 33_545 ?
O4 Fe2 O4 180.0 2_655 32 ?
O4 Fe2 O4 91.02(6) 31_655 32 ?
O3 Fe1 O3 93.19(7) 3_565 2_665 ?
O3 Fe1 O3 93.19(7) 3_565 . ?
O3 Fe1 O3 93.19(7) . 2_665 ?
O2 Fe1 O3 175.77(7) 3_565 . ?
O2 Fe1 O3 175.77(6) . 2_665 ?
O2 Fe1 O3 84.02(7) . 3_565 ?
O2 Fe1 O3 84.03(7) 3_565 2_665 ?
O2 Fe1 O3 90.15(7) 3_565 3_565 ?
O2 Fe1 O3 175.77(6) 2_665 3_565 ?
O2 Fe1 O3 84.02(7) 2_665 . ?
O2 Fe1 O3 90.15(7) 2_665 2_665 ?
O2 Fe1 O3 90.15(7) . . ?
O2 Fe1 O2 92.78(8) 3_565 . ?
O2 Fe1 O2 92.79(8) 3_565 2_665 ?
O2 Fe1 O2 92.78(8) . 2_665 ?
C4 O4 Fe2 127.61(15) . . ?
C4 O3 Fe1 126.22(17) . . ?
C5 O2 Fe1 125.9(2) . . ?
O4 C4 H4 117.0 . . ?
O3 C4 O4 125.9(2) . . ?
O3 C4 H4 117.0 . . ?
O2 C5 O2 127.4(3) 4 . ?
O2 C5 H5 116.3 4 . ?
O2 C5 H5 116.3 . . ?
H1A N1 H1C 109.5 . . ?
H1A N1 H1B 109.5 . . ?
H1C N1 H1B 109.4 . . ?
C1 N1 H1A 111.6 . . ?
C1 N1 H1C 106.9 . . ?
C1 N1 H1B 109.8 . . ?
H3A C3 H3B 109.4 . . ?
H3A C3 H3C 109.4 . . ?
H3B C3 H3C 109.4 . . ?
N2 C3 H3A 108.6 . . ?
N2 C3 H3B 110.1 . . ?
N2 C3 H3C 109.8 . . ?
N1 O1 H1F 75.6 3 . ?
N1 O1 H1G 78.4 3 . ?
H1F O1 H1G 101.5 . . ?
H2A C2 H2B 107.4 . . ?
N2 C2 H2A 108.3 . . ?
N2 C2 H2B 108.3 . . ?
N2 C2 C1 115.9(16) . . ?
C1 C2 H2A 108.3 . . ?
C1 C2 H2B 108.3 . . ?
C3 N2 H2D 107.4 . . ?
C3 N2 H2C 108.5 . . ?
C2 N2 C3 117.1(19) . . ?
C2 N2 H2D 113.1 . . ?
C2 N2 H2C 102.8 . . ?
H2D N2 H2C 107.4 . . ?
N1 C1 C2 108.9(15) . . ?
N1 C1 H1D 104.0 . . ?
N1 C1 H1E 108.4 . . ?
C2 C1 H1D 118.4 . . ?
C2 C1 H1E 109.8 . . ?
H1D C1 H1E 106.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C4 H4 O3 0.93 2.66 3.239(3) 121.3 3_565 yes
N1 H1A O1 0.89 1.62 2.45(3) 154.6 . yes
N1 H1C O3 0.89 2.36 3.052(19) 134.1 5_565 yes
N1 H1B O3 0.89 2.59 3.265(19) 133.3 6_655 yes
N1 H1B O2 0.89 2.14 2.96(2) 153.4 4 yes
C3 H3A O3 0.96 2.72 3.67(2) 171.9 3_565 yes
C3 H3B O3 0.96 2.20 3.13(5) 163.7 2_655 yes
C3 H3C O3 0.96 2.48 3.15(5) 127.2 1_445 yes
O1 H1F O4 0.81 2.64 3.22(6) 129.7 4_445 yes
O1 H1F O3 0.81 2.26 3.07(3) 176.8 4_445 yes
O1 H1G O4 0.74 2.38 3.12(7) 176.1 6_655 yes
N2 H2D O2 0.89 2.35 3.09(2) 140.1 3 yes
N2 H2C O3 0.89 2.41 3.03(2) 126.4 1_445 yes
N2 H2C O2 0.89 2.23 3.08(2) 158.1 2 yes
C1 H1D O2 0.97 2.32 3.09(4) 136.5 5 yes
C1 H1E O2 0.97 2.53 3.19(5) 125.3 6 yes

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
Fe2 O4 C4 O3 179.81(18) . . . . ?
Fe1 O3 C4 O4 168.58(18) . . . . ?
Fe1 O2 C5 O2 175.68(19) . . . 4 ?
N2 C2 C1 N1 -177(5) . . . . ?
C1 C2 N2 C3 175(4) . . . . ?

_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 1.340
_oxdiff_exptl_absorpt_empirical_full_min 0.734
_exptl_crystal_preparation       'Magnetic properties'
####################################################################### 
# 
# 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_3HTP
_database_code_depnum_ccdc_archive 'CCDC 2470387'
loop_
_audit_author_name
_audit_author_address
'Jiong-Peng Zhao'
;Tianjin University Of Technology
China
;
_audit_update_record             
;
2025-07-07 deposited with the CCDC.	2025-09-15 downloaded from the CCDC.
;
_audit_creation_date             2025-06-02
_audit_creation_method           
;
Olex2 1.5-ac6-020
(compiled 2024.02.14 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6966)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H9 Fe3 O18, 0.333(C18 H54 N6)'
_chemical_formula_sum            'C15 H27 Fe3 N2 O18'
_chemical_formula_weight         690.93
_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'
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      trigonal
_space_group_IT_number           167
_space_group_name_H-M_alt        'R -3 c'
_space_group_name_Hall           '-R 3 2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+5/6'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+7/6'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z-1/6'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+1/6'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'

_cell_length_a                   8.4183(6)
_cell_length_b                   8.4183(6)
_cell_length_c                   63.025(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3868.0(7)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    928
_cell_measurement_temperature    422.98(10)
_cell_measurement_theta_max      25.9720
_cell_measurement_theta_min      2.8830
_shelx_estimated_absorpt_T_max   0.844
_shelx_estimated_absorpt_T_min   0.622
_exptl_absorpt_coefficient_mu    1.750
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82249
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.9f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.780
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2118
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       67
_diffrn_reflns_limit_l_min       -74
_diffrn_reflns_number            3540
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.868
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      422.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  30.00   0.50    2.00    --   12.90 -57.00 -60.00  166
  2  ω    -71.00   5.00   0.50    2.00    --  -13.20 -77.00 -90.00  152
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual offset/far'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0773598000
_diffrn_orient_matrix_UB_12      0.0681447000
_diffrn_orient_matrix_UB_13      -0.0055669000
_diffrn_orient_matrix_UB_21      0.0227733000
_diffrn_orient_matrix_UB_22      0.0598354000
_diffrn_orient_matrix_UB_23      0.0088234000
_diffrn_orient_matrix_UB_31      0.0543229000
_diffrn_orient_matrix_UB_32      -0.0351813000
_diffrn_orient_matrix_UB_33      0.0042329000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                567
_reflns_number_total             768
_reflns_odcompleteness_completeness 99.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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       'CrysAlisPro 1.171.39.9f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.9f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.9f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    
'olex2.solve 1.5-ac6-020 (Bourhis et al., 2015)'
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     84
_refine_ls_number_reflns         768
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0342
_refine_ls_restrained_S_all      1.143
_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)+(0.0422P)²+6.8628P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0942
_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,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C5-C4
 1.54 with sigma of 0.02
 N1-C4
 1.52 with sigma of 0.02
 N1-C3
 1.52 with sigma of 0.02
 C3-C3_$1
 1.52 with sigma of 0.02
 C4-C3
 2.45 with sigma of 0.02
3. Restrained planarity
 C3, C5, C4, N1
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(C5) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C3) \\sim
Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Others
 Fixed Sof: C3(0.333333) H3B(0.333333) H3A(0.333333) N1(0.333333)
 H1A(0.333333) H1B(0.333333) C4(0.333333) H4A(0.333333) H4B(0.333333)
 C5(0.333333) H5A(0.333333) H5B(0.333333) H5C(0.333333)
6.a Riding coordinates:
 C3(H3B,H3A), N1(H1A,H1B)
6.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
6.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C1(H1)
6.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   mixed
_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
Fe2 Fe 0.666667 0.333333 0.333333 0.0241(3) Uani 1 6 d S T P . .
Fe1 Fe 0.333333 0.666667 0.27745(2) 0.0276(3) Uani 1 3 d S T P . .
O3 O 0.6613(3) 0.5267(3) 0.31522(3) 0.0468(6) Uani 1 1 d . . . . .
O2 O 0.5414(3) 0.6589(3) 0.29623(3) 0.0541(7) Uani 1 1 d . . . . .
O1 O 0.3198(3) 0.4484(3) 0.25928(4) 0.0602(7) Uani 1 1 d . . . . .
C2 C 0.5331(5) 0.5326(5) 0.30639(4) 0.0457(9) Uani 1 1 d . . . . .
H2 H 0.417758 0.428791 0.307685 0.055 Uiso 1 1 calc R U . . .
C1 C 0.4476(6) 0.4476(6) 0.250000 0.0494(13) Uani 1 2 d S T P . .
H1 H 0.558119 0.558121 0.250000 0.059 Uiso 1 2 calc R U P . .
C3 C 0.990(3) 1.062(3) 0.25835(15) 0.109(7) Uani 0.3333 1 d D U P . .
H3B H 1.025864 1.187713 0.255489 0.131 Uiso 0.3333 1 d R U P A .
H3A H 0.859954 0.988613 0.260029 0.131 Uiso 0.3333 1 d R U P . .
N1 N 1.0905(19) 1.043(3) 0.2773(2) 0.125(6) Uani 0.3333 1 d D U P A -1
H1A H 1.094465 0.943131 0.276288 0.150 Uiso 0.3333 1 d R U P A -1
H1B H 1.189965 1.145741 0.279238 0.150 Uiso 0.3333 1 d R U P A -1
C4 C 0.945(3) 1.014(4) 0.2949(2) 0.114(7) Uani 0.3333 1 d D U P A -1
H4A H 0.927487 1.119136 0.295832 0.137 Uiso 0.3333 1 calc R U P A -1
H4B H 0.827373 0.905177 0.291971 0.137 Uiso 0.3333 1 calc R U P A -1
C5 C 1.029(8) 0.990(9) 0.3152(2) 0.151(12) Uani 0.3333 1 d D U P A -1
H5A H 0.948887 0.972220 0.326901 0.226 Uiso 0.3333 1 calc R U P A -1
H5B H 1.145563 1.098447 0.317560 0.226 Uiso 0.3333 1 calc R U P A -1
H5C H 1.045345 0.886005 0.313796 0.226 Uiso 0.3333 1 calc R 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
Fe2 O3 2.007(2) 31_655 ?
Fe2 O3 2.007(2) 2_655 ?
Fe2 O3 2.007(2) 3_665 ?
Fe2 O3 2.007(2) 32 ?
Fe2 O3 2.007(2) 33_545 ?
Fe2 O3 2.007(2) . ?
Fe1 O2 2.141(2) 2_665 ?
Fe1 O2 2.141(2) . ?
Fe1 O2 2.141(2) 3_565 ?
Fe1 O1 2.120(2) 3_565 ?
Fe1 O1 2.120(2) . ?
Fe1 O1 2.120(2) 2_665 ?
O3 C2 1.237(4) . ?
O2 C2 1.213(3) . ?
O1 C1 1.227(3) . ?
C2 H2 0.9300 . ?
C1 H1 0.9300 . ?
C3 C3 1.39(3) 5_675 ?
C3 C3 1.061(19) 6_765 ?
C3 C3 1.485(16) 4 ?
C3 C3 0.98(2) 2_765 ?
C3 C3 0.98(2) 3_675 ?
C3 H3B 0.9601 . ?
C3 H3A 1.02(3) 3_675 ?
C3 H3A 0.9600 . ?
C3 N1 1.518(13) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C4 1.579(14) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.519(19) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?

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
O3 Fe2 O3 90.84(9) 31_655 32 ?
O3 Fe2 O3 179.985(1) 33_545 3_665 ?
O3 Fe2 O3 90.83(9) . 2_655 ?
O3 Fe2 O3 90.85(9) 31_655 33_545 ?
O3 Fe2 O3 89.17(9) 31_655 2_655 ?
O3 Fe2 O3 90.85(9) 32 33_545 ?
O3 Fe2 O3 89.16(9) 32 3_665 ?
O3 Fe2 O3 179.990(1) 31_655 . ?
O3 Fe2 O3 90.83(9) . 3_665 ?
O3 Fe2 O3 89.16(9) 32 . ?
O3 Fe2 O3 179.985(1) 32 2_655 ?
O3 Fe2 O3 89.16(9) 33_545 . ?
O3 Fe2 O3 90.82(9) 3_665 2_655 ?
O3 Fe2 O3 89.16(9) 31_655 3_665 ?
O3 Fe2 O3 89.17(9) 33_545 2_655 ?
O2 Fe1 O2 92.41(9) 3_565 . ?
O2 Fe1 O2 92.41(9) 2_665 . ?
O2 Fe1 O2 92.41(9) 2_665 3_565 ?
O1 Fe1 O2 87.85(10) 3_565 3_565 ?
O1 Fe1 O2 86.20(9) 2_665 . ?
O1 Fe1 O2 87.85(10) 2_665 2_665 ?
O1 Fe1 O2 178.59(9) 2_665 3_565 ?
O1 Fe1 O2 87.86(10) . . ?
O1 Fe1 O2 86.20(9) 3_565 2_665 ?
O1 Fe1 O2 178.59(9) . 2_665 ?
O1 Fe1 O2 178.59(9) 3_565 . ?
O1 Fe1 O2 86.20(9) . 3_565 ?
O1 Fe1 O1 93.54(10) 2_665 . ?
O1 Fe1 O1 93.54(10) 3_565 . ?
O1 Fe1 O1 93.54(10) 3_565 2_665 ?
C2 O3 Fe2 131.5(2) . . ?
C2 O2 Fe1 129.0(2) . . ?
C1 O1 Fe1 126.5(3) . . ?
O3 C2 H2 116.4 . . ?
O2 C2 O3 127.2(3) . . ?
O2 C2 H2 116.4 . . ?
O1 C1 O1 128.3(5) . 4 ?
O1 C1 H1 115.8 4 . ?
O1 C1 H1 115.8 . . ?
C3 C3 C3 60.00(3) 3_675 2_765 ?
C3 C3 C3 41.5(11) 6_765 4 ?
C3 C3 C3 45.6(9) 3_675 4 ?
C3 C3 C3 85.5(17) 3_675 6_765 ?
C3 C3 C3 44.9(11) 6_765 5_675 ?
C3 C3 C3 92.9(6) 2_765 6_765 ?
C3 C3 C3 64.9(17) 2_765 4 ?
C3 C3 C3 75.2(19) 3_675 5_675 ?
C3 C3 C3 49.6(16) 2_765 5_675 ?
C3 C3 C3 39.9(8) 5_675 4 ?
C3 C3 H3B 126.3 3_675 . ?
C3 C3 H3B 77.2 6_765 . ?
C3 C3 H3B 118.7 5_675 . ?
C3 C3 H3B 167.1 2_765 . ?
C3 C3 H3B 110.4 4 . ?
C3 C3 H3A 117.0(12) 2_765 3_675 ?
C3 C3 H3A 57.3(12) 3_675 3_675 ?
C3 C3 H3A 112.5 4 . ?
C3 C3 H3A 116.3(6) 5_675 3_675 ?
C3 C3 H3A 73.6 5_675 . ?
C3 C3 H3A 88(3) 6_765 3_675 ?
C3 C3 H3A 122.5 3_675 . ?
C3 C3 H3A 76.6(14) 4 3_675 ?
C3 C3 H3A 103.8 6_765 . ?
C3 C3 H3A 63.0 2_765 . ?
C3 C3 N1 122.4(17) 5_675 . ?
C3 C3 N1 53.4(9) 3_675 . ?
C3 C3 N1 80.4(12) 2_765 . ?
C3 C3 N1 98.9(14) 4 . ?
C3 C3 N1 136(3) 6_765 . ?
H3B C3 H3A 110.9 . . ?
H3B C3 H3A 71.6 . 3_675 ?
H3A C3 H3A 167.7 . 3_675 ?
N1 C3 H3B 112.5 . . ?
N1 C3 H3A 111.2 . . ?
N1 C3 H3A 57.9(7) . 3_675 ?
C3 N1 H3A 41.3(12) . 3_675 ?
C3 N1 H1A 109.8 . . ?
C3 N1 H1B 108.4 . . ?
C3 N1 C4 98.0(10) . . ?
H1A N1 H3A 115.6 . 3_675 ?
H1A N1 H1B 120.0 . . ?
H1B N1 H3A 71.1 . 3_675 ?
C4 N1 H3A 127.8(16) . 3_675 ?
C4 N1 H1A 107.9 . . ?
C4 N1 H1B 110.4 . . ?
N1 C4 H4A 111.1 . . ?
N1 C4 H4B 111.1 . . ?
H4A C4 H4B 109.0 . . ?
C5 C4 N1 103.5(15) . . ?
C5 C4 H4A 111.1 . . ?
C5 C4 H4B 111.1 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C3 H3B O1 0.96 2.36 3.04(2) 127.5 1_665 yes
C3 H3A O1 0.96 2.27 3.21(2) 165.7 2_665 yes
N1 H1A O2 0.86 2.69 3.247(14) 124.2 2_765 yes
N1 H1B O1 0.86 2.55 3.175(19) 130.7 1_665 yes
C4 H4A O2 0.97 2.48 3.27(3) 138.6 3_675 yes
C4 H4B O2 0.97 2.27 3.21(3) 161.9 . yes
C5 H5A O3 0.96 3.57 3.81(4) 97.4 3_675 yes

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
Fe2 O3 C2 O2 177.2(2) . . . . ?
Fe1 O2 C2 O3 171.6(2) . . . . ?
Fe1 O1 C1 O1 173.9(2) . . . 4 ?
C3 C3 N1 C4 -151.0(13) 4 . . . ?
C3 C3 N1 C4 -116(2) 5_675 . . . ?
C3 C3 N1 C4 -173(3) 6_765 . . . ?
C3 C3 N1 C4 -148(3) 3_675 . . . ?
C3 C3 N1 C4 -89(2) 2_765 . . . ?
C3 N1 C4 C5 179.6(17) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.109
_oxdiff_exptl_absorpt_empirical_full_min 0.894
########END
####################################################################### 
# 
# 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_2HTP
_database_code_depnum_ccdc_archive 'CCDC 2470385'
loop_
_audit_author_name
_audit_author_address
'Jiong-Peng Zhao'
;Tianjin University Of Technology
China
;
_audit_update_record             
;
2025-07-07 deposited with the CCDC.	2025-09-15 downloaded from the CCDC.
;
_audit_creation_date             2025-06-02
_audit_creation_method           
;
Olex2 1.5-ac6-020
(compiled 2024.02.14 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6966)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H9 Fe3 O18, 0.333(C12 H42 N6)'
_chemical_formula_sum            'C13 H23 Fe3 N2 O18'
_chemical_formula_weight         662.88
_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'
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      trigonal
_space_group_IT_number           167
_space_group_name_H-M_alt        'R -3 c'
_space_group_name_Hall           '-R 3 2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+5/6'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+7/6'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z-1/6'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+1/6'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'

_cell_length_a                   8.2967(5)
_cell_length_b                   8.2967(5)
_cell_length_c                   62.793(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3743.3(6)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    5418
_cell_measurement_temperature    393.00(10)
_cell_measurement_theta_max      29.8460
_cell_measurement_theta_min      3.8600
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.805
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.20103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.63a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            BLACK
_exptl_crystal_colour_primary    BLACK
_exptl_crystal_density_diffrn    1.764
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             2022
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0734
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       81
_diffrn_reflns_limit_l_min       -83
_diffrn_reflns_number            5625
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.760
_diffrn_reflns_theta_min         3.845
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      393.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -59.00  28.00   0.50    1.71    --    0.00 -57.00 -30.00  174
  2  ω    -89.00 -47.00   0.50    1.71    --    0.00 -77.00 120.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual offset/far'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0965936000
_diffrn_orient_matrix_UB_12      -0.0304282000
_diffrn_orient_matrix_UB_13      -0.0000285000
_diffrn_orient_matrix_UB_21      -0.0132409000
_diffrn_orient_matrix_UB_22      -0.0610265000
_diffrn_orient_matrix_UB_23      -0.0085721000
_diffrn_orient_matrix_UB_31      -0.0157069000
_diffrn_orient_matrix_UB_32      -0.0713140000
_diffrn_orient_matrix_UB_33      0.0073507000
_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              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                814
_reflns_number_total             1105
_reflns_odcompleteness_completeness 99.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.42.63a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.63a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.63a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.750
_refine_diff_density_min         -0.575
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       0.0068(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     75
_refine_ls_number_reflns         1105
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0378
_refine_ls_restrained_S_all      1.115
_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)+(0.0568P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1083
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H) groups, All C(H,H,H) groups, All N(H,H) groups
2. Restrained distances
 N1_$1-C3_$1
 1.53 with sigma of 0.02
 N1_$2-C3_$2 = N1_$2-C4 = C3_$3-C3_$2 = N1_$3-C3_$3 = N1_$3-C4_$3
 1.53 with sigma of 0.02
3. Rigid bond restraints
 C3, N1, C4
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C4 \\sim N1 \\sim C3: within 3.8A with sigma of 0.01 and sigma for terminal
atoms of 0.03 within 3.8A
Uanis(C4) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C3) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.2
5. Rigid body (RIGU) restrains
 C4, N1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: N1(0.333333) H1a(0.333333) H1b(0.333333) C3(0.333333)
 H3b(0.333333) H3a(0.333333) C4(0.333333) H4a(0.333333) H4b(0.333333)
 H4c(0.333333)
7.a Riding coordinates:
 N1(H1a,H1b), C3(H3b,H3a), C4(H4a,H4b,H4c)
7.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C1(H1)
;
_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
Fe2 Fe 0.333333 0.666667 0.666667 0.0176(2) Uani 1 6 d S T P . .
Fe1 Fe 0.666667 0.333333 0.72217(2) 0.0206(2) Uani 1 3 d S T P . .
O3 O 0.5363(2) 0.67371(19) 0.68469(2) 0.0327(4) Uani 1 1 d . . . . .
O2 O 0.6691(2) 0.5494(2) 0.70359(2) 0.0426(4) Uani 1 1 d . . . . .
O1 O 0.8713(2) 0.5567(2) 0.74046(3) 0.0550(5) Uani 1 1 d . . . . .
C2 C 0.5413(3) 0.5397(3) 0.69299(3) 0.0352(5) Uani 1 1 d . . . . .
H2 H 0.438518 0.421987 0.690905 0.042 Uiso 1 1 calc R U . . .
C1 C 1.000000 0.5546(4) 0.750000 0.0376(7) Uani 1 2 d S T P . .
H1 H 1.000000 0.442487 0.750000 0.045 Uiso 1 2 calc R U P . .
N1 N 0.9100(14) 0.9480(14) 0.72241(18) 0.098(3) Uani 0.3333 1 d . U P . .
H1A H 0.837883 0.999854 0.724040 0.147 Uiso 0.3333 1 d R U P A .
H1B H 0.836823 0.823524 0.723070 0.147 Uiso 0.3333 1 d R U P . .
C3 C 1.0497(17) 1.008(3) 0.74011(12) 0.105(4) Uani 0.3333 1 d . U P A .
H3B H 1.130662 1.140042 0.738933 0.158 Uiso 0.3333 1 d R U P . .
H3A H 1.123642 0.949342 0.738543 0.158 Uiso 0.3333 1 d R U P . .
C4 C 1.016(5) 0.982(4) 0.7010(3) 0.136(8) Uani 0.3333 1 d D U P A -1
H4A H 0.926963 0.940619 0.689774 0.204 Uiso 0.3333 1 d R U P A -1
H4B H 1.094303 1.114729 0.700434 0.204 Uiso 0.3333 1 d R U P A -1
H4C H 1.093153 0.925369 0.699394 0.204 Uiso 0.3333 1 d R 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
Fe2 O3 2.0056(13) 2_665 ?
Fe2 O3 2.0055(13) . ?
Fe2 O3 2.0056(13) 25_566 ?
Fe2 O3 2.0055(13) 26_456 ?
Fe2 O3 2.0056(14) 3_565 ?
Fe2 O3 2.0055(14) 27_556 ?
Fe1 O2 2.1304(14) . ?
Fe1 O2 2.1304(15) 2_655 ?
Fe1 O2 2.1304(14) 3_665 ?
Fe1 O1 2.1189(15) 3_665 ?
Fe1 O1 2.1188(15) . ?
Fe1 O1 2.1189(15) 2_655 ?
O3 C2 1.247(2) . ?
O2 C2 1.220(2) . ?
O1 C1 1.232(2) . ?
C2 H2 0.9300 . ?
C1 H1 0.9300 . ?
N1 N1 1.125(19) 3_675 ?
N1 N1 1.125(18) 2_765 ?
N1 H1A 0.9003 . ?
N1 H1A 1.444(17) 2_765 ?
N1 H1B 0.9000 . ?
N1 C3 1.500(9) . ?
N1 C3 1.332(17) 2_765 ?
N1 C3 1.178(12) 3_675 ?
N1 C4 1.553(16) . ?
N1 H4B 1.438(12) 2_765 ?
C3 C3 0.66(2) 3_675 ?
C3 C3 0.664(19) 2_765 ?
C3 C3 1.38(2) 4_556 ?
C3 C3 1.247(14) 5_676 ?
C3 C3 1.432(15) 6_766 ?
C3 H3B 0.9601 . ?
C3 H3A 0.9596 . ?
C4 H4A 0.9550 . ?
C4 H4B 0.9613 . ?
C4 H4B 1.08(6) 2_765 ?
C4 H4C 0.9661 . ?

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
O3 Fe2 O3 91.26(6) 2_665 . ?
O3 Fe2 O3 180.00(6) . 25_566 ?
O3 Fe2 O3 88.73(6) . 27_556 ?
O3 Fe2 O3 180.0 2_665 26_456 ?
O3 Fe2 O3 88.74(6) 3_565 25_566 ?
O3 Fe2 O3 88.73(6) 2_665 27_556 ?
O3 Fe2 O3 91.26(6) 2_665 3_565 ?
O3 Fe2 O3 91.27(6) 25_566 27_556 ?
O3 Fe2 O3 88.73(6) . 26_456 ?
O3 Fe2 O3 88.74(6) 3_565 26_456 ?
O3 Fe2 O3 91.26(6) . 3_565 ?
O3 Fe2 O3 91.27(6) 25_566 26_456 ?
O3 Fe2 O3 91.27(6) 27_556 26_456 ?
O3 Fe2 O3 88.74(6) 2_665 25_566 ?
O3 Fe2 O3 180.0 3_565 27_556 ?
O2 Fe1 O2 92.88(6) 3_665 2_655 ?
O2 Fe1 O2 92.88(6) 3_665 . ?
O2 Fe1 O2 92.88(6) 2_655 . ?
O1 Fe1 O2 89.92(7) 3_665 2_655 ?
O1 Fe1 O2 89.91(7) . 3_665 ?
O1 Fe1 O2 83.95(6) . . ?
O1 Fe1 O2 175.88(6) . 2_655 ?
O1 Fe1 O2 89.92(7) 2_655 . ?
O1 Fe1 O2 83.96(6) 3_665 3_665 ?
O1 Fe1 O2 175.88(6) 3_665 . ?
O1 Fe1 O2 175.88(6) 2_655 3_665 ?
O1 Fe1 O2 83.96(6) 2_655 2_655 ?
O1 Fe1 O1 93.38(8) 3_665 2_655 ?
O1 Fe1 O1 93.39(7) . 3_665 ?
O1 Fe1 O1 93.39(7) . 2_655 ?
C2 O3 Fe2 127.68(15) . . ?
C2 O2 Fe1 126.94(16) . . ?
C1 O1 Fe1 124.92(17) . . ?
O3 C2 H2 117.1 . . ?
O2 C2 O3 125.7(2) . . ?
O2 C2 H2 117.1 . . ?
O1 C1 O1 126.8(3) 6_766 . ?
O1 C1 H1 116.6 6_766 . ?
O1 C1 H1 116.6 . . ?
N1 N1 N1 60.00(2) 3_675 2_765 ?
N1 N1 H1A 98.4(5) 3_675 2_765 ?
N1 N1 H1A 38.6(6) 2_765 2_765 ?
N1 N1 H1A 90.3 3_675 . ?
N1 N1 H1A 149.6 2_765 . ?
N1 N1 H1B 160.7 3_675 . ?
N1 N1 H1B 100.9 2_765 . ?
N1 N1 C3 81.2(8) 3_675 3_675 ?
N1 N1 C3 56.6(11) 3_675 2_765 ?
N1 N1 C3 58.9(9) 3_675 . ?
N1 N1 C3 74.7(10) 2_765 2_765 ?
N1 N1 C3 70.6(12) 2_765 3_675 ?
N1 N1 C3 50.9(6) 2_765 . ?
N1 N1 C4 60.7(12) 2_765 . ?
N1 N1 C4 70.0(13) 3_675 . ?
N1 N1 H4B 102.6(14) 2_765 2_765 ?
N1 N1 H4B 87.4(14) 3_675 2_765 ?
H1A N1 H1A 166.3 . 2_765 ?
H1A N1 H1B 108.4 . . ?
H1A N1 H4B 80.4 . 2_765 ?
H1A N1 H4B 110.4 2_765 2_765 ?
H1B N1 H1A 62.4 . 2_765 ?
H1B N1 H4B 100.2 . 2_765 ?
C3 N1 H1A 100.8 3_675 . ?
C3 N1 H1A 66.3(9) . 2_765 ?
C3 N1 H1A 83.9 2_765 . ?
C3 N1 H1A 110.2 . . ?
C3 N1 H1A 92.0(7) 2_765 2_765 ?
C3 N1 H1A 70.4(12) 3_675 2_765 ?
C3 N1 H1B 108.2 . . ?
C3 N1 H1B 119.1 2_765 . ?
C3 N1 H1B 90.2 3_675 . ?
C3 N1 C3 29.9(9) 3_675 2_765 ?
C3 N1 C3 25.3(8) 3_675 . ?
C3 N1 C3 26.3(8) 2_765 . ?
C3 N1 C4 107.8(14) . . ?
C3 N1 C4 130.9(18) 3_675 . ?
C3 N1 C4 122.5(19) 2_765 . ?
C3 N1 H4B 140.6(17) 2_765 2_765 ?
C3 N1 H4B 168.6(18) 3_675 2_765 ?
C3 N1 H4B 143.9(17) . 2_765 ?
C4 N1 H1A 75.4(12) . 2_765 ?
C4 N1 H1A 117.7 . . ?
C4 N1 H1B 104.0 . . ?
C4 N1 H4B 42(2) . 2_765 ?
N1 C3 N1 47.8(9) 2_765 . ?
N1 C3 N1 46.3(8) 3_675 . ?
N1 C3 N1 52.8(10) 2_765 3_675 ?
N1 C3 H1B 67.3(8) 3_675 2_765 ?
N1 C3 H1B 83.9(8) . 2_765 ?
N1 C3 H1B 37.3(4) 2_765 2_765 ?
N1 C3 C3 133.8(10) 3_675 6_766 ?
N1 C3 C3 167.8(15) 2_765 4_556 ?
N1 C3 C3 145.6(17) 2_765 6_766 ?
N1 C3 C3 122(2) 3_675 4_556 ?
N1 C3 C3 156(3) 2_765 5_676 ?
N1 C3 H3B 100.4 2_765 . ?
N1 C3 H3B 62.6 3_675 . ?
N1 C3 H3B 107.7 . . ?
N1 C3 H3A 113.7 3_675 . ?
N1 C3 H3A 67.7 2_765 . ?
N1 C3 H3A 109.9 . . ?
C3 C3 N1 88.0(19) 3_675 2_765 ?
C3 C3 N1 62.6(15) 2_765 . ?
C3 C3 N1 135.4(16) 5_676 . ?
C3 C3 N1 108.0(13) 6_766 . ?
C3 C3 N1 105.6(8) 2_765 2_765 ?
C3 C3 N1 151(3) 5_676 3_675 ?
C3 C3 N1 49.2(6) 3_675 . ?
C3 C3 N1 120.1(16) 4_556 . ?
C3 C3 N1 91.1(17) 3_675 3_675 ?
C3 C3 N1 62.2(18) 2_765 3_675 ?
C3 C3 H1B 129(2) 2_765 2_765 ?
C3 C3 H1B 158.5(9) 6_766 2_765 ?
C3 C3 H1B 154.7(8) 4_556 2_765 ?
C3 C3 H1B 124(3) 3_675 2_765 ?
C3 C3 H1B 136.0(7) 5_676 2_765 ?
C3 C3 C3 60.5(8) 3_675 6_766 ?
C3 C3 C3 86.7(18) 3_675 5_676 ?
C3 C3 C3 72(2) 2_765 6_766 ?
C3 C3 C3 64.5(17) 2_765 4_556 ?
C3 C3 C3 91.9(5) 2_765 5_676 ?
C3 C3 C3 28.8(8) 5_676 4_556 ?
C3 C3 C3 27.6(8) 5_676 6_766 ?
C3 C3 C3 60.00(8) 3_675 2_765 ?
C3 C3 C3 81(2) 3_675 4_556 ?
C3 C3 C3 27.3(7) 4_556 6_766 ?
C3 C3 H3B 135.8 3_675 . ?
C3 C3 H3B 84.4 4_556 . ?
C3 C3 H3B 111.7 6_766 . ?
C3 C3 H3B 99.6 5_676 . ?
C3 C3 H3B 76.0 2_765 . ?
C3 C3 H3A 115.1 3_675 . ?
C3 C3 H3A 111.4 6_766 . ?
C3 C3 H3A 121.6 4_556 . ?
C3 C3 H3A 93.6 5_676 . ?
C3 C3 H3A 172.5 2_765 . ?
H3B C3 H1B 80.2 . 2_765 ?
H3B C3 H3A 108.1 . . ?
H3A C3 H1B 47.0 . 2_765 ?
N1 C4 H4A 107.8 . . ?
N1 C4 H4B 103.6 . . ?
N1 C4 H4B 63.2(11) . 2_765 ?
N1 C4 H4C 117.2 . . ?
H4A C4 H4B 51.2 . 2_765 ?
H4A C4 H4B 109.8 . . ?
H4A C4 H4C 109.3 . . ?
H4B C4 H4B 96.4 . 2_765 ?
H4B C4 H4C 108.9 . . ?
H4C C4 H4B 153.1 . 2_765 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A O1 0.90 2.27 3.130(10) 159.4 3_675 yes
N1 H1B O2 0.90 2.33 3.117(10) 145.7 . yes
N1 H1B O1 0.90 2.61 3.300(11) 134.1 . yes
C3 H3B O1 0.96 2.25 2.972(17) 130.8 2_765 yes
C3 H3A O1 0.96 2.57 3.29(2) 131.7 6_766 yes
C4 H4C O2 0.97 2.59 3.19(3) 121.1 2_765 yes

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
Fe2 O3 C2 O2 178.69(17) . . . . ?
Fe1 O2 C2 O3 169.21(16) . . . . ?
Fe1 O1 C1 O1 174.55(19) . . . 6_766 ?
N1 N1 C3 N1 -74.8(6) 3_675 . . 2_765 ?
N1 N1 C3 N1 74.8(6) 2_765 . . 3_675 ?
N1 N1 C3 C3 107(2) 3_675 . . 4_556 ?
N1 N1 C3 C3 -151.1(13) 2_765 . . 6_766 ?
N1 N1 C3 C3 138(4) 3_675 . . 5_676 ?
N1 N1 C3 C3 149(5) 3_675 . . 3_675 ?
N1 N1 C3 C3 -136(5) 2_765 . . 3_675 ?
N1 N1 C3 C3 -147(5) 2_765 . . 5_676 ?
N1 N1 C3 C3 77(4) 3_675 . . 2_765 ?
N1 N1 C3 C3 134.1(9) 3_675 . . 6_766 ?
N1 N1 C3 C3 -178(2) 2_765 . . 4_556 ?
N1 N1 C3 C3 151(4) 2_765 . . 2_765 ?
C3 N1 C3 N1 -149(5) 3_675 . . 3_675 ?
C3 N1 C3 N1 136(5) 3_675 . . 2_765 ?
C3 N1 C3 N1 -77(4) 2_765 . . 3_675 ?
C3 N1 C3 N1 -151(4) 2_765 . . 2_765 ?
C3 N1 C3 C3 61.9(8) 2_765 . . 5_676 ?
C3 N1 C3 C3 -15(4) 3_675 . . 6_766 ?
C3 N1 C3 C3 -72.7(9) 3_675 . . 2_765 ?
C3 N1 C3 C3 30.7(19) 2_765 . . 4_556 ?
C3 N1 C3 C3 -10.9(8) 3_675 . . 5_676 ?
C3 N1 C3 C3 72.7(11) 2_765 . . 3_675 ?
C3 N1 C3 C3 -42(3) 3_675 . . 4_556 ?
C3 N1 C3 C3 58(3) 2_765 . . 6_766 ?
C4 N1 C3 N1 -22.6(16) . . . 2_765 ?
C4 N1 C3 N1 52.2(14) . . . 3_675 ?
C4 N1 C3 C3 -159(4) . . . 3_675 ?
C4 N1 C3 C3 -173.7(12) . . . 6_766 ?
C4 N1 C3 C3 -169(4) . . . 5_676 ?
C4 N1 C3 C3 159.4(18) . . . 4_556 ?
C4 N1 C3 C3 129(3) . . . 2_765 ?

_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 2.842
_oxdiff_exptl_absorpt_empirical_full_min 0.539
