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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_rdt92b-150k
_database_code_depnum_ccdc_archive 'CCDC 2075294'
loop_
_audit_author_name
_audit_author_address
'David Harding'
;Walailak University
Thailand
;
_audit_update_record             
;
2021-04-05 deposited with the CCDC.	2021-05-14 downloaded from the CCDC.
;
_audit_creation_date             2020-08-06
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H13 F Fe N3 O5, C H4 O'
_chemical_formula_sum            'C24 H17 F Fe N3 O6'
_chemical_formula_weight         518.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         C24H17FeFN3O6
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1982(3)
_cell_length_b                   11.5358(5)
_cell_length_c                   12.9597(6)
_cell_angle_alpha                103.868(4)
_cell_angle_beta                 103.308(4)
_cell_angle_gamma                107.779(4)
_cell_volume                     1070.33(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7696
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      68.3500
_cell_measurement_theta_min      3.6850
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.168
_exptl_absorpt_correction_T_max  0.736
_exptl_absorpt_correction_T_min  0.202
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.81a (Rigaku Oxford Diffraction, 2020)
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    1.608
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             530
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 0 -5 0.1187
-4 0 5 0.0722
1 5 -4 0.1829
1 -5 2 0.2039
0 0 -1 0.0297
0 0 1 0.0222
4 0 3 0.1037
-3 0 -4 0.0705
0 -7 3 0.1728
-3 1 -6 0.0607
2 0 -8 0.0710

_exptl_crystal_size_max          0.483
_exptl_crystal_size_mid          0.222
_exptl_crystal_size_min          0.052
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
3.9880 0.0247 -5.0315 -0.2555 -0.8356 -0.0101
-3.9880 -0.0247 5.0315 0.2555 0.8356 0.0101
0.9854 5.0164 -3.9812 -0.0738 -0.4478 -0.6707
1.0094 -5.0062 1.9674 0.0100 0.0397 0.6717
-0.0017 0.0044 -1.0039 -0.1280 -0.0193 -0.0121
0.0017 -0.0044 1.0039 0.1280 0.0193 0.0121
4.0017 -0.0105 2.9995 0.7686 -0.6810 0.0863
-3.0042 0.0156 -4.0064 -0.8005 0.4769 -0.0858
0.0730 -7.1423 3.2648 -0.0593 0.3182 0.9462
-2.5417 0.8387 -5.7504 -0.9227 0.3267 -0.2045
2.0939 0.4236 -8.2167 -0.8180 -0.5623 -0.1212

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0798
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15309
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.832
_diffrn_reflns_theta_min         3.719
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -88.00  -5.00   0.50    0.30    --  -40.91 123.00-131.00  166
  2  ω   -104.00 -18.00   0.50    0.30    --  -40.91 148.00  32.00  172
  3  ω     18.00 104.00   0.50    0.30    --   40.91-148.00 -15.00  172
  4  ω     78.00 157.00   0.50    1.00    --   96.59 123.00-131.00  158
  5  ω     33.00 128.00   0.50    1.00    --   96.59-148.00 -15.00  190
  6  ω     33.00 110.00   0.50    1.00    --   96.59-123.00 148.00  154
  7  ω     63.00 157.00   0.50    1.00    --   96.59 148.00  32.00  188
  8  ω   -105.00 -29.00   0.50    0.30    --  -40.91 -37.00-180.00  152
  9  ω   -104.00 -25.00   0.50    0.30    --  -40.91 -50.00 -30.00  158
 10  ω   -109.00 -32.00   0.50    0.30    --  -40.91 -25.00 120.00  154
 11  ω    -23.00  61.00   0.50    0.30    --   40.91 -63.00 -60.00  168
 12  ω     25.00 104.00   0.50    0.30    --   40.91  50.00-120.00  158
 13  ω    -24.00  67.00   0.50    0.30    --   40.91 -77.00   0.00  182
 14  ω     14.00  97.00   0.50    0.30    --   40.91-138.00 -90.00  166
 15  ω      5.00  88.00   0.50    0.30    --   40.91-123.00 148.00  166
 16  ω     19.00 114.00   0.50    0.30    --   40.91  12.00 120.00  190
 17  ω    -23.00  53.00   0.50    0.30    --   40.91 -37.00 -30.00  152
 18  ω    -23.00  53.00   0.50    0.30    --   40.91 -37.00 120.00  152
 19  ω     32.00 109.00   0.50    1.00    --   96.59-117.00 -30.00  154
 20  ω     67.00 157.00   0.50    1.00    --   96.59   8.00  30.00  180
 21  ω     33.00 118.00   0.50    1.00    --   96.59 -68.00 120.00  170
 22  ω     27.00 105.00   0.50    1.00    --   96.59 -96.00 -30.00  156
 23  ω     67.00 157.00   0.50    1.00    --   96.59   8.00 -60.00  180
 24  ω     26.00 110.00   0.50    1.00    --   96.59 -17.00 -90.00  168
 25  ω     84.00 157.00   0.50    1.00    --   96.59  96.00 -90.00  146
 26  ω     84.00 157.00   0.50    1.00    --   96.59  42.00-120.00  146
 27  ω     31.00 106.00   0.50    1.00    --   96.59 -33.00   0.00  150
 28  ω     31.00 124.00   0.50    1.00    --   96.59 -86.00  60.00  186
 29  ω     32.00 109.00   0.50    1.00    --   96.59-117.00-150.00  154
 30  ω     33.00 118.00   0.50    1.00    --   96.59 -68.00 -60.00  170
 31  ω     32.00 109.00   0.50    1.00    --   96.59-117.00  60.00  154
 32  ω     67.00 157.00   0.50    1.00    --   96.59 144.00   0.00  180
 33  ω     34.00 110.00   0.50    1.00    --   96.59 -42.00-150.00  152
 34  ω     81.00 157.00   0.50    1.00    --   96.59 117.00-150.00  152
 35  ω     81.00 157.00   0.50    1.00    --   96.59 117.00   0.00  152
 36  ω     34.00 110.00   0.50    1.00    --   96.59 -42.00 -60.00  152
 37  ω     26.00 110.00   0.50    1.00    --   96.59 -17.00  90.00  168
 38  ω     34.00 110.00   0.50    1.00    --   96.59 -42.00  90.00  152
 39  ω     75.00 157.00   0.50    1.00    --   96.59  68.00 120.00  164
 40  ω   -104.00 -21.00   0.50    0.30    --  -40.91 -63.00  60.00  166
 41  ω   -104.00 -21.00   0.50    0.30    --  -40.91 -63.00 120.00  166
 42  ω   -104.00 -25.00   0.50    0.30    --  -40.91 -50.00 -90.00  158
 43  ω   -104.00 -21.00   0.50    0.30    --  -40.91 -63.00  30.00  166
 44  ω   -104.00 -21.00   0.50    0.30    --  -40.91 -63.00-180.00  166
 45  ω   -104.00 -21.00   0.50    0.30    --  -40.91 -63.00 -60.00  166
 46  ω   -104.00 -21.00   0.50    0.30    --  -40.91 -63.00  90.00  166
 47  ω   -104.00 -21.00   0.50    0.30    --  -40.91 -63.00 -30.00  166
 48  ω   -104.00 -21.00   0.50    0.30    --  -40.91 -63.00-120.00  166
 49  ω   -104.00 -21.00   0.50    0.30    --  -40.91 -63.00 150.00  166
 50  ω   -104.00 -21.00   0.50    0.30    --  -40.91 -63.00   0.00  166
 51  ω     21.00 105.00   0.50    0.30    --   40.91  63.00 -60.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0965599000
_diffrn_orient_matrix_UB_12      0.0676365000
_diffrn_orient_matrix_UB_13      0.1276499000
_diffrn_orient_matrix_UB_21      -0.1848183000
_diffrn_orient_matrix_UB_22      -0.0375678000
_diffrn_orient_matrix_UB_23      0.0193959000
_diffrn_orient_matrix_UB_31      0.0126736000
_diffrn_orient_matrix_UB_32      -0.1271227000
_diffrn_orient_matrix_UB_33      0.0114281000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3397
_reflns_number_total             3880
_reflns_odcompleteness_completeness 99.24
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.050
_refine_diff_density_min         -0.780
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         3880
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0629
_refine_ls_restrained_S_all      1.101
_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)+(0.1108P)²+0.3872P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1706
_refine_ls_wR_factor_ref         0.1762
_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,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C10(H10), C12(H12), C14(H14),
 C15(H15), C19(H19), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
2.c Idealised tetrahedral OH refined as rotating group:
 O6(H6A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.21127(7) 0.29430(5) 0.70123(5) 0.0305(2) Uani 1 1 d . . . . .
F1 F -0.2956(4) -0.2864(2) 0.7314(3) 0.0603(8) Uani 1 1 d . . . . .
O1 O 0.1548(4) 0.2046(3) 0.8002(2) 0.0428(7) Uani 1 1 d . . . . .
O2 O 0.3398(4) 0.1888(3) 0.6311(2) 0.0405(7) Uani 1 1 d . . . . .
O3 O 0.6015(5) 0.1700(4) 0.6325(3) 0.0689(11) Uani 1 1 d . . . . .
O4 O 0.2167(4) 0.4623(3) 0.8065(2) 0.0424(7) Uani 1 1 d . . . . .
O5 O 0.3924(6) 0.6529(3) 0.9405(3) 0.0658(10) Uani 1 1 d . . . . .
N1 N 0.1898(4) 0.3783(3) 0.5702(3) 0.0326(7) Uani 1 1 d . . . . .
N2 N -0.0426(4) 0.1720(3) 0.5828(3) 0.0311(7) Uani 1 1 d . . . . .
N3 N 0.4825(4) 0.4026(3) 0.7879(3) 0.0314(7) Uani 1 1 d . . . . .
C1 C 0.3127(5) 0.4853(4) 0.5690(4) 0.0388(9) Uani 1 1 d . . . . .
H1 H 0.420578 0.527776 0.629154 0.047 Uiso 1 1 calc R U . . .
C2 C 0.2865(6) 0.5358(4) 0.4818(4) 0.0464(11) Uani 1 1 d . . . . .
H2 H 0.375320 0.610364 0.484299 0.056 Uiso 1 1 calc R U . . .
C3 C 0.1284(6) 0.4745(4) 0.3925(4) 0.0441(10) Uani 1 1 d . . . . .
H3 H 0.108963 0.507142 0.333778 0.053 Uiso 1 1 calc R U . . .
C4 C -0.0041(6) 0.3618(4) 0.3903(3) 0.0379(9) Uani 1 1 d . . . . .
C5 C -0.1706(6) 0.2938(4) 0.3023(4) 0.0472(10) Uani 1 1 d . . . . .
H5 H -0.196012 0.320709 0.240381 0.057 Uiso 1 1 calc R U . . .
C6 C -0.2942(7) 0.1879(4) 0.3088(4) 0.0512(11) Uani 1 1 d . . . . .
H6 H -0.403760 0.142973 0.250229 0.061 Uiso 1 1 calc R U . . .
C7 C -0.2617(6) 0.1445(4) 0.4009(4) 0.0456(10) Uani 1 1 d . . . . .
H7 H -0.350842 0.073881 0.403971 0.055 Uiso 1 1 calc R U . . .
C8 C -0.0998(5) 0.2058(3) 0.4859(3) 0.0336(8) Uani 1 1 d . . . . .
C9 C 0.0324(5) 0.3171(3) 0.4818(3) 0.0313(8) Uani 1 1 d . . . . .
C10 C -0.1410(5) 0.0626(3) 0.5884(3) 0.0336(8) Uani 1 1 d . . . . .
H10 H -0.247173 0.011751 0.528361 0.040 Uiso 1 1 calc R U . . .
C11 C -0.1007(5) 0.0143(3) 0.6774(3) 0.0323(8) Uani 1 1 d . . . . .
C12 C -0.2176(6) -0.1120(4) 0.6644(4) 0.0402(9) Uani 1 1 d . . . . .
H12 H -0.317681 -0.159401 0.599666 0.048 Uiso 1 1 calc R U . . .
C13 C -0.1819(6) -0.1630(4) 0.7473(4) 0.0407(10) Uani 1 1 d . . . . .
C14 C -0.0360(6) -0.0991(4) 0.8444(4) 0.0455(10) Uani 1 1 d . . . . .
H14 H -0.013669 -0.138742 0.897744 0.055 Uiso 1 1 calc R U . . .
C15 C 0.0772(6) 0.0251(4) 0.8614(4) 0.0435(10) Uani 1 1 d . . . . .
H15 H 0.174744 0.070311 0.927731 0.052 Uiso 1 1 calc R U . . .
C16 C 0.0470(5) 0.0838(4) 0.7799(3) 0.0342(8) Uani 1 1 d . . . . .
C17 C 0.5125(6) 0.2269(4) 0.6695(4) 0.0434(10) Uani 1 1 d . . . . .
C18 C 0.6031(5) 0.3533(4) 0.7669(3) 0.0367(9) Uani 1 1 d . . . . .
C19 C 0.7843(6) 0.4166(5) 0.8291(4) 0.0499(11) Uani 1 1 d . . . . .
H19 H 0.868277 0.381055 0.815905 0.060 Uiso 1 1 calc R U . . .
C20 C 0.8369(6) 0.5324(5) 0.9101(5) 0.0583(13) Uani 1 1 d . . . . .
H20 H 0.959245 0.577814 0.951440 0.070 Uiso 1 1 calc R U . . .
C21 C 0.7111(6) 0.5847(4) 0.9326(4) 0.0525(12) Uani 1 1 d . . . . .
H21 H 0.747551 0.663664 0.988675 0.063 Uiso 1 1 calc R U . . .
C22 C 0.5305(6) 0.5153(3) 0.8688(3) 0.0385(9) Uani 1 1 d . . . . .
C23 C 0.3691(6) 0.5496(4) 0.8750(4) 0.0446(10) Uani 1 1 d . . . . .
O6 O 0.7980(5) 0.2115(3) 0.9807(4) 0.0675(10) Uani 1 1 d . . . . .
H6A H 0.754498 0.252898 1.018888 0.101 Uiso 1 1 calc R U . . .
C24 C 0.6605(7) 0.0993(5) 0.9023(5) 0.0634(14) Uani 1 1 d . . . . .
H24A H 0.690258 0.077828 0.834668 0.095 Uiso 1 1 calc R U . . .
H24B H 0.548682 0.112726 0.885694 0.095 Uiso 1 1 calc R U . . .
H24C H 0.647378 0.029952 0.932480 0.095 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
Fe1 O1 1.883(3) . ?
Fe1 O2 2.027(3) . ?
Fe1 O4 2.067(3) . ?
Fe1 N1 2.147(3) . ?
Fe1 N2 2.092(3) . ?
Fe1 N3 2.061(3) . ?
F1 C13 1.378(4) . ?
O1 C16 1.327(5) . ?
O2 C17 1.279(5) . ?
O3 C17 1.224(5) . ?
O4 C23 1.287(5) . ?
O5 C23 1.216(5) . ?
N1 C1 1.339(5) . ?
N1 C9 1.361(5) . ?
N2 C8 1.423(5) . ?
N2 C10 1.303(5) . ?
N3 C18 1.329(5) . ?
N3 C22 1.337(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.394(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.370(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.406(6) . ?
C4 C5 1.407(6) . ?
C4 C9 1.410(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.363(7) . ?
C6 H6 0.9300 . ?
C6 C7 1.403(7) . ?
C7 H7 0.9300 . ?
C7 C8 1.362(6) . ?
C8 C9 1.426(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.413(6) . ?
C11 C12 1.424(5) . ?
C11 C16 1.424(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.360(6) . ?
C13 C14 1.372(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.380(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.400(6) . ?
C17 C18 1.515(6) . ?
C18 C19 1.376(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.356(8) . ?
C20 H20 0.9300 . ?
C20 C21 1.395(7) . ?
C21 H21 0.9300 . ?
C21 C22 1.382(6) . ?
C22 C23 1.507(6) . ?
O6 H6A 0.8200 . ?
O6 C24 1.389(6) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
O1 Fe1 O2 97.43(13) . . ?
O1 Fe1 O4 91.65(12) . . ?
O1 Fe1 N1 162.98(12) . . ?
O1 Fe1 N2 88.54(12) . . ?
O1 Fe1 N3 99.56(12) . . ?
O2 Fe1 O4 150.86(12) . . ?
O2 Fe1 N1 91.40(11) . . ?
O2 Fe1 N2 92.96(12) . . ?
O2 Fe1 N3 75.88(12) . . ?
O4 Fe1 N1 87.57(12) . . ?
O4 Fe1 N2 114.99(12) . . ?
N2 Fe1 N1 76.44(12) . . ?
N3 Fe1 O4 75.33(12) . . ?
N3 Fe1 N1 96.69(12) . . ?
N3 Fe1 N2 166.90(12) . . ?
C16 O1 Fe1 130.8(3) . . ?
C17 O2 Fe1 120.2(2) . . ?
C23 O4 Fe1 119.8(3) . . ?
C1 N1 Fe1 126.5(3) . . ?
C1 N1 C9 117.9(3) . . ?
C9 N1 Fe1 115.5(2) . . ?
C8 N2 Fe1 117.0(2) . . ?
C10 N2 Fe1 123.6(3) . . ?
C10 N2 C8 119.1(3) . . ?
C18 N3 Fe1 118.6(3) . . ?
C18 N3 C22 122.1(3) . . ?
C22 N3 Fe1 119.1(3) . . ?
N1 C1 H1 118.5 . . ?
N1 C1 C2 123.1(4) . . ?
C2 C1 H1 118.5 . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.3(4) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.5(4) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 123.0(4) . . ?
C3 C4 C9 117.8(4) . . ?
C5 C4 C9 119.2(4) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.2(4) . . ?
C6 C5 H5 120.4 . . ?
C5 C6 H6 118.9 . . ?
C5 C6 C7 122.2(4) . . ?
C7 C6 H6 118.9 . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 120.1(4) . . ?
C8 C7 H7 120.0 . . ?
N2 C8 C9 113.6(3) . . ?
C7 C8 N2 127.3(4) . . ?
C7 C8 C9 119.1(4) . . ?
N1 C9 C4 122.4(3) . . ?
N1 C9 C8 117.4(3) . . ?
C4 C9 C8 120.2(4) . . ?
N2 C10 H10 117.1 . . ?
N2 C10 C11 125.9(4) . . ?
C11 C10 H10 117.1 . . ?
C10 C11 C12 117.6(4) . . ?
C10 C11 C16 124.7(3) . . ?
C12 C11 C16 117.7(4) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.5(4) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 F1 118.1(4) . . ?
C12 C13 C14 123.3(4) . . ?
C14 C13 F1 118.5(4) . . ?
C13 C14 H14 120.6 . . ?
C13 C14 C15 118.8(4) . . ?
C15 C14 H14 120.6 . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.8(4) . . ?
C16 C15 H15 119.6 . . ?
O1 C16 C11 120.8(4) . . ?
O1 C16 C15 119.3(4) . . ?
C15 C16 C11 119.9(3) . . ?
O2 C17 C18 114.0(3) . . ?
O3 C17 O2 124.8(4) . . ?
O3 C17 C18 121.2(4) . . ?
N3 C18 C17 111.0(3) . . ?
N3 C18 C19 120.9(4) . . ?
C19 C18 C17 128.1(4) . . ?
C18 C19 H19 120.9 . . ?
C20 C19 C18 118.1(5) . . ?
C20 C19 H19 120.9 . . ?
C19 C20 H20 119.4 . . ?
C19 C20 C21 121.3(4) . . ?
C21 C20 H20 119.4 . . ?
C20 C21 H21 121.0 . . ?
C22 C21 C20 117.9(4) . . ?
C22 C21 H21 121.0 . . ?
N3 C22 C21 119.7(4) . . ?
N3 C22 C23 111.7(3) . . ?
C21 C22 C23 128.7(4) . . ?
O4 C23 C22 113.8(3) . . ?
O5 C23 O4 126.8(5) . . ?
O5 C23 C22 119.3(4) . . ?
C24 O6 H6A 109.5 . . ?
O6 C24 H24A 109.5 . . ?
O6 C24 H24B 109.5 . . ?
O6 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Fe1 O1 C16 C11 -25.3(5) . . . . ?
Fe1 O1 C16 C15 155.9(3) . . . . ?
Fe1 O2 C17 O3 -179.8(4) . . . . ?
Fe1 O2 C17 C18 -0.6(5) . . . . ?
Fe1 O4 C23 O5 179.2(4) . . . . ?
Fe1 O4 C23 C22 -0.2(5) . . . . ?
Fe1 N1 C1 C2 -178.2(3) . . . . ?
Fe1 N1 C9 C4 178.6(3) . . . . ?
Fe1 N1 C9 C8 0.3(4) . . . . ?
Fe1 N2 C8 C7 -176.7(3) . . . . ?
Fe1 N2 C8 C9 3.1(4) . . . . ?
Fe1 N2 C10 C11 5.2(5) . . . . ?
Fe1 N3 C18 C17 6.4(4) . . . . ?
Fe1 N3 C18 C19 -174.4(3) . . . . ?
Fe1 N3 C22 C21 175.7(3) . . . . ?
Fe1 N3 C22 C23 -5.3(4) . . . . ?
F1 C13 C14 C15 -179.3(4) . . . . ?
O2 Fe1 O1 C16 -65.1(3) . . . . ?
O2 C17 C18 N3 -3.7(5) . . . . ?
O2 C17 C18 C19 177.2(4) . . . . ?
O3 C17 C18 N3 175.5(4) . . . . ?
O3 C17 C18 C19 -3.6(7) . . . . ?
O4 Fe1 O1 C16 142.7(3) . . . . ?
N1 Fe1 O1 C16 55.6(6) . . . . ?
N1 C1 C2 C3 0.0(6) . . . . ?
N2 Fe1 O1 C16 27.7(3) . . . . ?
N2 C8 C9 N1 -2.1(5) . . . . ?
N2 C8 C9 C4 179.5(3) . . . . ?
N2 C10 C11 C12 -175.2(3) . . . . ?
N2 C10 C11 C16 5.7(6) . . . . ?
N3 Fe1 O1 C16 -141.9(3) . . . . ?
N3 C18 C19 C20 -1.8(6) . . . . ?
N3 C22 C23 O4 3.5(5) . . . . ?
N3 C22 C23 O5 -176.0(4) . . . . ?
C1 N1 C9 C4 0.4(5) . . . . ?
C1 N1 C9 C8 -178.0(3) . . . . ?
C1 C2 C3 C4 -0.1(6) . . . . ?
C2 C3 C4 C5 179.4(4) . . . . ?
C2 C3 C4 C9 0.3(6) . . . . ?
C3 C4 C5 C6 -177.7(4) . . . . ?
C3 C4 C9 N1 -0.4(5) . . . . ?
C3 C4 C9 C8 177.9(3) . . . . ?
C4 C5 C6 C7 0.4(7) . . . . ?
C5 C4 C9 N1 -179.6(3) . . . . ?
C5 C4 C9 C8 -1.3(5) . . . . ?
C5 C6 C7 C8 -2.4(7) . . . . ?
C6 C7 C8 N2 -177.7(4) . . . . ?
C6 C7 C8 C9 2.5(6) . . . . ?
C7 C8 C9 N1 177.7(3) . . . . ?
C7 C8 C9 C4 -0.7(5) . . . . ?
C8 N2 C10 C11 178.6(3) . . . . ?
C9 N1 C1 C2 -0.1(5) . . . . ?
C9 C4 C5 C6 1.4(6) . . . . ?
C10 N2 C8 C7 9.4(6) . . . . ?
C10 N2 C8 C9 -170.8(3) . . . . ?
C10 C11 C12 C13 178.9(3) . . . . ?
C10 C11 C16 O1 3.0(6) . . . . ?
C10 C11 C16 C15 -178.2(3) . . . . ?
C11 C12 C13 F1 -178.8(3) . . . . ?
C11 C12 C13 C14 -0.7(6) . . . . ?
C12 C11 C16 O1 -176.1(3) . . . . ?
C12 C11 C16 C15 2.7(5) . . . . ?
C12 C13 C14 C15 2.6(6) . . . . ?
C13 C14 C15 C16 -1.8(6) . . . . ?
C14 C15 C16 O1 177.9(4) . . . . ?
C14 C15 C16 C11 -0.8(6) . . . . ?
C16 C11 C12 C13 -1.9(5) . . . . ?
C17 C18 C19 C20 177.2(4) . . . . ?
C18 N3 C22 C21 0.8(6) . . . . ?
C18 N3 C22 C23 179.8(3) . . . . ?
C18 C19 C20 C21 1.9(7) . . . . ?
C19 C20 C21 C22 -0.6(7) . . . . ?
C20 C21 C22 N3 -0.7(6) . . . . ?
C20 C21 C22 C23 -179.5(4) . . . . ?
C21 C22 C23 O4 -177.6(4) . . . . ?
C21 C22 C23 O5 2.9(7) . . . . ?
C22 N3 C18 C17 -178.7(3) . . . . ?
C22 N3 C18 C19 0.5(6) . . . . ?

_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 3.783
_oxdiff_exptl_absorpt_empirical_full_min 0.422
####################################################################### 
# 
# 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_rdt-40-2
_database_code_depnum_ccdc_archive 'CCDC 2075297'
loop_
_audit_author_name
_audit_author_address
'David Harding'
;Walailak University
Thailand
;
_audit_update_record             
;
2021-04-05 deposited with the CCDC.	2021-05-14 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT971_rdt-40-2            
;
PROBLEM: Check Calcd Resid. Dens.  1.00A   From I1              2.87 eA-3
RESPONSE: Several different absorption corrections methods were used but despite this large peaks remain around the iodine atom.
;
_vrf_PLAT971_rdt-40-2_2          
;
PROBLEM: Check Calcd Resid. Dens.  0.93A   From I1              2.83 eA-3
RESPONSE: Several different absorption corrections methods were used but despite this large peaks remain around the iodine atom.
;
_vrf_PLAT972_rdt-40-2            
;
PROBLEM: Check Calcd Resid. Dens.  0.88A   From I1             -2.68 eA-3
RESPONSE: Several different absorption corrections methods were used but despite this large holes remain around the iodine atom.
;
# Added during the CSD deposition process: Monday 05 April 2021 02:44 AM
# end Validation Reply Form

_audit_creation_date             2020-02-06
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H13 Fe I N3 O5, C H4 O'
_chemical_formula_sum            'C24 H17 Fe I N3 O6'
_chemical_formula_weight         626.15
_chemical_melting_point          ?
_chemical_oxdiff_formula         C24H17FeIN3O6
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   12.1991(2)
_cell_length_b                   9.3756(2)
_cell_length_c                   19.0747(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.6028(19)
_cell_angle_gamma                90
_cell_volume                     2171.23(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8019
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.3520
_cell_measurement_theta_min      4.1110
_shelx_estimated_absorpt_T_max   0.526
_shelx_estimated_absorpt_T_min   0.232
_exptl_absorpt_coefficient_mu    17.172
_exptl_absorpt_correction_T_max  0.596
_exptl_absorpt_correction_T_min  0.230
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.916
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1236
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 1 1 0.0614
5 0 -1 0.0458
1 5 1 0.0338
-1 0 -5 0.0315
1 0 5 0.0113
-2 -5 0 0.0667
-3 0 5 0.0338
1 0 -5 0.0370
5 -5 1 0.0689

_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.043
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
-4.9983 0.9972 0.9725 -0.1146 -0.6408 0.0390
4.9977 0.0034 -0.9866 0.1222 0.5879 -0.1945
0.9943 5.0085 0.9313 -0.0333 -0.1334 -0.8261
-0.9883 -0.0210 -5.0000 0.3912 -0.1759 0.0796
0.9883 0.0210 5.0000 -0.3912 0.1759 -0.0796
-1.9955 -5.0061 0.0656 -0.0551 0.0248 0.8588
-3.0082 0.0151 4.9897 -0.4250 -0.3034 0.0823
1.0100 -0.0181 -4.9949 0.4081 0.0638 -0.0014
4.9961 -4.9919 1.0831 -0.0757 0.8747 0.5676

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0708
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17238
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.582
_diffrn_reflns_theta_min         4.126
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -109.00 -32.00   0.50    6.20    --  -40.91 -25.00-163.00  154
  2  ω    -50.00  27.00   0.50    6.20    --  -40.91  25.00   0.00  154
  3  ω     32.00 109.00   0.50    6.20    --   40.91  25.00   0.00  154
  4  ω     88.00 157.00   0.50   20.00    --   96.59  25.00   0.00  138
  5  ω     29.00 105.00   0.50   20.00    --   96.59 -25.00-163.00  152
  6  ω    -97.00 -14.00   0.50    6.20    --  -40.91 138.00  90.00  166
  7  ω    -53.00  23.00   0.50    6.20    --  -40.91  37.00  90.00  152
  8  ω    -32.00  63.00   0.50    6.20    --   40.91 -12.00 -30.00  190
  9  ω    -27.00  50.00   0.50    6.20    --   40.91 -25.00-163.00  154
 10  ω     21.00 105.00   0.50    6.20    --   40.91  63.00 150.00  168
 11  ω     29.00 105.00   0.50    6.20    --   40.91  37.00 120.00  152
 12  ω    -23.00  53.00   0.50    6.20    --   40.91 -37.00 -90.00  152
 13  ω    -24.00  67.00   0.50    6.20    --   40.91 -77.00  90.00  182
 14  ω     29.00 105.00   0.50   20.00    --   96.59 -25.00 120.00  152
 15  ω     34.00 110.00   0.50   20.00    --   96.59 -42.00 -60.00  152
 16  ω     31.00 106.00   0.50   20.00    --   96.59 -33.00  30.00  150
 17  ω     22.00 127.00   0.50   20.00    --   96.59  -8.00 -30.00  210
 18  ω     32.00 109.00   0.50   20.00    --   96.59-117.00 -90.00  154
 19  ω     27.00 105.00   0.50   20.00    --   96.59 -96.00 150.00  156
 20  ω     33.00 118.00   0.50   20.00    --   96.59 -68.00 -60.00  170
 21  ω     33.00 126.00   0.50   20.00    --   96.59-144.00 -90.00  186
 22  ω     32.00 109.00   0.50   20.00    --   96.59-117.00 150.00  154
 23  ω     34.00 113.00   0.50   20.00    --   96.59 -50.00 -90.00  158
 24  ω   -104.00 -21.00   0.50    6.20    --  -40.91 -63.00-180.00  166
 25  ω   -104.00 -21.00   0.50    6.20    --  -40.91 -63.00 -90.00  166
 26  ω   -104.00 -21.00   0.50    6.20    --  -40.91 -63.00   0.00  166
 27  ω   -104.00 -21.00   0.50    6.20    --  -40.91 -63.00  60.00  166
 28  ω   -104.00 -21.00   0.50    6.20    --  -40.91 -63.00 120.00  166
 29  ω     21.00 105.00   0.50    6.20    --   40.91  63.00  30.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0086679000
_diffrn_orient_matrix_UB_12      0.0064973000
_diffrn_orient_matrix_UB_13      -0.0799720000
_diffrn_orient_matrix_UB_21      0.1199732000
_diffrn_orient_matrix_UB_22      -0.0526207000
_diffrn_orient_matrix_UB_23      0.0116855000
_diffrn_orient_matrix_UB_31      -0.0402606000
_diffrn_orient_matrix_UB_32      -0.1555904000
_diffrn_orient_matrix_UB_33      -0.0073027000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3411
_reflns_number_total             3969
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT n/a (Sheldrick, 2015)'
_refine_diff_density_max         2.876
_refine_diff_density_min         -2.609
_refine_diff_density_rms         0.174
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         3969
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0598
_refine_ls_restrained_S_all      1.092
_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)+(0.1067P)²+4.6645P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1651
_refine_ls_wR_factor_ref         0.1704
_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,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C10(H10), C12(H12), C14(H14),
 C15(H15), C19(H19), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
2.c Idealised tetrahedral OH refined as rotating group:
 O6(H6A)
;
_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
I1 I 0.56058(3) 0.77517(5) 0.22929(2) 0.0339(2) Uani 1 1 d . . . . .
Fe1 Fe 0.26094(7) 0.28517(10) 0.47069(5) 0.0235(3) Uani 1 1 d . . . . .
O1 O 0.2461(3) 0.3947(5) 0.3862(2) 0.0279(9) Uani 1 1 d . . . . .
O2 O 0.1648(3) 0.1285(5) 0.4215(2) 0.0266(9) Uani 1 1 d . . . . .
O3 O -0.0010(3) 0.0248(5) 0.4079(2) 0.0301(10) Uani 1 1 d . . . . .
O4 O 0.2816(3) 0.4491(5) 0.5413(2) 0.0287(9) Uani 1 1 d . . . . .
O5 O 0.2115(4) 0.5756(5) 0.6261(2) 0.0352(11) Uani 1 1 d . . . . .
N1 N 0.3239(4) 0.1254(6) 0.5442(3) 0.0259(11) Uani 1 1 d . . . . .
N2 N 0.4337(4) 0.2967(5) 0.4667(3) 0.0245(11) Uani 1 1 d . . . . .
N3 N 0.1094(4) 0.3061(5) 0.5109(3) 0.0221(10) Uani 1 1 d . . . . .
C1 C 0.2636(5) 0.0358(7) 0.5785(3) 0.0295(14) Uani 1 1 d . . . . .
H1 H 0.187331 0.041223 0.570280 0.035 Uiso 1 1 calc R U . . .
C2 C 0.3093(5) -0.0665(7) 0.6267(3) 0.0291(14) Uani 1 1 d . . . . .
H2 H 0.264319 -0.129765 0.648153 0.035 Uiso 1 1 calc R U . . .
C3 C 0.4222(5) -0.0711(7) 0.6414(3) 0.0292(13) Uani 1 1 d . . . . .
H3 H 0.454365 -0.136109 0.673994 0.035 Uiso 1 1 calc R U . . .
C4 C 0.4884(5) 0.0235(7) 0.6066(3) 0.0260(13) Uani 1 1 d . . . . .
C5 C 0.6057(5) 0.0274(7) 0.6187(3) 0.0289(13) Uani 1 1 d . . . . .
H5 H 0.642379 -0.034732 0.651000 0.035 Uiso 1 1 calc R U . . .
C6 C 0.6641(5) 0.1228(7) 0.5827(3) 0.0274(13) Uani 1 1 d . . . . .
H6 H 0.740392 0.126133 0.591671 0.033 Uiso 1 1 calc R U . . .
C7 C 0.6113(5) 0.2156(7) 0.5324(4) 0.0273(13) Uani 1 1 d . . . . .
H7 H 0.653068 0.278494 0.508295 0.033 Uiso 1 1 calc R U . . .
C8 C 0.4980(5) 0.2147(6) 0.5182(3) 0.0250(13) Uani 1 1 d . . . . .
C9 C 0.4363(5) 0.1187(7) 0.5573(3) 0.0252(13) Uani 1 1 d . . . . .
C10 C 0.4825(5) 0.3825(6) 0.4260(3) 0.0261(13) Uani 1 1 d . . . . .
H10 H 0.559035 0.385796 0.432605 0.031 Uiso 1 1 calc R U . . .
C11 C 0.4303(5) 0.4716(7) 0.3724(3) 0.0253(13) Uani 1 1 d . . . . .
C12 C 0.4986(5) 0.5589(7) 0.3355(3) 0.0277(13) Uani 1 1 d . . . . .
H12 H 0.574452 0.556384 0.346762 0.033 Uiso 1 1 calc R U . . .
C13 C 0.4546(5) 0.6480(7) 0.2829(3) 0.0305(14) Uani 1 1 d . . . . .
C14 C 0.3410(5) 0.6509(7) 0.2646(3) 0.0316(14) Uani 1 1 d . . . . .
H14 H 0.311487 0.710491 0.228621 0.038 Uiso 1 1 calc R U . . .
C15 C 0.2725(5) 0.5659(8) 0.2998(3) 0.0315(14) Uani 1 1 d . . . . .
H15 H 0.196966 0.568645 0.287265 0.038 Uiso 1 1 calc R U . . .
C16 C 0.3148(5) 0.4750(7) 0.3543(3) 0.0260(13) Uani 1 1 d . . . . .
C17 C 0.0628(5) 0.1146(7) 0.4329(3) 0.0253(13) Uani 1 1 d . . . . .
C18 C 0.0270(5) 0.2238(6) 0.4849(4) 0.0270(13) Uani 1 1 d . . . . .
C19 C -0.0764(5) 0.2412(7) 0.5078(4) 0.0275(14) Uani 1 1 d . . . . .
H19 H -0.135369 0.185780 0.489079 0.033 Uiso 1 1 calc R U . . .
C20 C -0.0907(5) 0.3418(7) 0.5589(3) 0.0296(14) Uani 1 1 d . . . . .
H20 H -0.159788 0.354414 0.574680 0.036 Uiso 1 1 calc R U . . .
C21 C -0.0021(5) 0.4249(7) 0.5871(3) 0.0265(13) Uani 1 1 d . . . . .
H21 H -0.010591 0.491721 0.622241 0.032 Uiso 1 1 calc R U . . .
C22 C 0.0991(5) 0.4044(7) 0.5609(3) 0.0262(13) Uani 1 1 d . . . . .
C23 C 0.2039(5) 0.4861(7) 0.5799(3) 0.0273(13) Uani 1 1 d . . . . .
O6 O 0.0005(5) -0.1873(7) 0.2905(3) 0.0569(15) Uani 1 1 d . . . . .
H6A H 0.023098 -0.121893 0.316552 0.085 Uiso 1 1 calc R U . . .
C24 C -0.1158(8) -0.1830(11) 0.2805(5) 0.057(2) Uani 1 1 d . . . . .
H24A H -0.142764 -0.117595 0.313549 0.086 Uiso 1 1 calc R U . . .
H24B H -0.144837 -0.276406 0.287738 0.086 Uiso 1 1 calc R U . . .
H24C H -0.138839 -0.151888 0.233394 0.086 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
I1 C13 2.097(6) . ?
Fe1 O1 1.904(4) . ?
Fe1 O2 2.049(4) . ?
Fe1 O4 2.044(4) . ?
Fe1 N1 2.142(5) . ?
Fe1 N2 2.119(5) . ?
Fe1 N3 2.079(5) . ?
O1 C16 1.319(7) . ?
O2 C17 1.290(7) . ?
O3 C17 1.212(7) . ?
O4 C23 1.302(7) . ?
O5 C23 1.214(8) . ?
N1 C1 1.331(8) . ?
N1 C9 1.370(7) . ?
N2 C8 1.421(9) . ?
N2 C10 1.302(8) . ?
N3 C18 1.325(8) . ?
N3 C22 1.341(8) . ?
C1 H1 0.9300 . ?
C1 C2 1.404(9) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.409(9) . ?
C4 C5 1.428(9) . ?
C4 C9 1.403(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.370(9) . ?
C6 H6 0.9300 . ?
C6 C7 1.404(9) . ?
C7 H7 0.9300 . ?
C7 C8 1.382(9) . ?
C8 C9 1.429(8) . ?
C10 H10 0.9300 . ?
C10 C11 1.423(9) . ?
C11 C12 1.405(8) . ?
C11 C16 1.418(8) . ?
C12 H12 0.9300 . ?
C12 C13 1.373(9) . ?
C13 C14 1.396(9) . ?
C14 H14 0.9300 . ?
C14 C15 1.376(9) . ?
C15 H15 0.9300 . ?
C15 C16 1.401(9) . ?
C17 C18 1.518(9) . ?
C18 C19 1.385(9) . ?
C19 H19 0.9300 . ?
C19 C20 1.380(10) . ?
C20 H20 0.9300 . ?
C20 C21 1.396(9) . ?
C21 H21 0.9300 . ?
C21 C22 1.390(8) . ?
C22 C23 1.504(9) . ?
O6 H6A 0.8200 . ?
O6 C24 1.414(11) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
O1 Fe1 O2 89.79(18) . . ?
O1 Fe1 O4 98.50(19) . . ?
O1 Fe1 N1 158.29(18) . . ?
O1 Fe1 N2 87.41(19) . . ?
O1 Fe1 N3 104.30(19) . . ?
O2 Fe1 N1 87.20(18) . . ?
O2 Fe1 N2 123.15(18) . . ?
O2 Fe1 N3 75.34(18) . . ?
O4 Fe1 O2 150.39(16) . . ?
O4 Fe1 N1 94.65(19) . . ?
O4 Fe1 N2 85.78(18) . . ?
O4 Fe1 N3 75.07(18) . . ?
N2 Fe1 N1 76.38(19) . . ?
N3 Fe1 N1 95.72(19) . . ?
N3 Fe1 N2 158.7(2) . . ?
C16 O1 Fe1 133.4(4) . . ?
C17 O2 Fe1 120.9(4) . . ?
C23 O4 Fe1 121.5(4) . . ?
C1 N1 Fe1 125.7(4) . . ?
C1 N1 C9 118.2(5) . . ?
C9 N1 Fe1 116.1(4) . . ?
C8 N2 Fe1 115.5(4) . . ?
C10 N2 Fe1 124.6(4) . . ?
C10 N2 C8 119.5(5) . . ?
C18 N3 Fe1 118.4(4) . . ?
C18 N3 C22 123.1(5) . . ?
C22 N3 Fe1 118.5(4) . . ?
N1 C1 H1 118.3 . . ?
N1 C1 C2 123.4(6) . . ?
C2 C1 H1 118.3 . . ?
C1 C2 H2 120.7 . . ?
C3 C2 C1 118.6(6) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.4(6) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 123.4(6) . . ?
C9 C4 C3 118.3(6) . . ?
C9 C4 C5 118.3(6) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.8(6) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 119.3 . . ?
C5 C6 C7 121.4(6) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 119.5 . . ?
C8 C7 C6 120.9(6) . . ?
C8 C7 H7 119.5 . . ?
N2 C8 C9 114.7(5) . . ?
C7 C8 N2 127.3(6) . . ?
C7 C8 C9 118.0(6) . . ?
N1 C9 C4 122.1(5) . . ?
N1 C9 C8 116.4(6) . . ?
C4 C9 C8 121.5(5) . . ?
N2 C10 H10 116.8 . . ?
N2 C10 C11 126.4(5) . . ?
C11 C10 H10 116.8 . . ?
C12 C11 C10 117.2(5) . . ?
C12 C11 C16 119.2(6) . . ?
C16 C11 C10 123.6(5) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.8(6) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 I1 119.1(4) . . ?
C12 C13 C14 120.1(6) . . ?
C14 C13 I1 120.8(5) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.1(6) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 119.4 . . ?
C14 C15 C16 121.1(6) . . ?
C16 C15 H15 119.4 . . ?
O1 C16 C11 122.4(6) . . ?
O1 C16 C15 119.0(5) . . ?
C15 C16 C11 118.6(5) . . ?
O2 C17 C18 112.7(5) . . ?
O3 C17 O2 126.6(6) . . ?
O3 C17 C18 120.7(5) . . ?
N3 C18 C17 112.4(5) . . ?
N3 C18 C19 119.6(6) . . ?
C19 C18 C17 127.9(6) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 C18 119.0(6) . . ?
C20 C19 H19 120.5 . . ?
C19 C20 H20 119.7 . . ?
C19 C20 C21 120.5(6) . . ?
C21 C20 H20 119.7 . . ?
C20 C21 H21 121.2 . . ?
C22 C21 C20 117.7(6) . . ?
C22 C21 H21 121.1 . . ?
N3 C22 C21 120.0(6) . . ?
N3 C22 C23 112.6(5) . . ?
C21 C22 C23 127.4(6) . . ?
O4 C23 C22 112.2(5) . . ?
O5 C23 O4 125.9(6) . . ?
O5 C23 C22 122.0(5) . . ?
C24 O6 H6A 109.5 . . ?
O6 C24 H24A 109.5 . . ?
O6 C24 H24B 109.5 . . ?
O6 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

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
I1 C13 C14 C15 179.3(5) . . . . ?
Fe1 O1 C16 C11 14.0(9) . . . . ?
Fe1 O1 C16 C15 -166.9(5) . . . . ?
Fe1 O2 C17 O3 -178.6(5) . . . . ?
Fe1 O2 C17 C18 -0.2(7) . . . . ?
Fe1 O4 C23 O5 175.0(5) . . . . ?
Fe1 O4 C23 C22 -5.2(7) . . . . ?
Fe1 N1 C1 C2 -179.5(5) . . . . ?
Fe1 N1 C9 C4 177.1(4) . . . . ?
Fe1 N1 C9 C8 -2.6(7) . . . . ?
Fe1 N2 C8 C7 -172.1(5) . . . . ?
Fe1 N2 C8 C9 10.0(6) . . . . ?
Fe1 N2 C10 C11 -7.1(9) . . . . ?
Fe1 N3 C18 C17 5.6(7) . . . . ?
Fe1 N3 C18 C19 -176.3(5) . . . . ?
Fe1 N3 C22 C21 177.6(5) . . . . ?
Fe1 N3 C22 C23 0.1(7) . . . . ?
O2 C17 C18 N3 -3.5(8) . . . . ?
O2 C17 C18 C19 178.6(6) . . . . ?
O3 C17 C18 N3 175.0(6) . . . . ?
O3 C17 C18 C19 -2.9(10) . . . . ?
N1 C1 C2 C3 2.7(10) . . . . ?
N2 C8 C9 N1 -4.8(8) . . . . ?
N2 C8 C9 C4 175.5(5) . . . . ?
N2 C10 C11 C12 178.5(6) . . . . ?
N2 C10 C11 C16 -2.2(10) . . . . ?
N3 C18 C19 C20 -1.7(10) . . . . ?
N3 C22 C23 O4 3.1(8) . . . . ?
N3 C22 C23 O5 -177.1(6) . . . . ?
C1 N1 C9 C4 -1.5(8) . . . . ?
C1 N1 C9 C8 178.8(5) . . . . ?
C1 C2 C3 C4 -1.7(9) . . . . ?
C2 C3 C4 C5 179.5(6) . . . . ?
C2 C3 C4 C9 -0.6(9) . . . . ?
C3 C4 C5 C6 -180.0(6) . . . . ?
C3 C4 C9 N1 2.3(9) . . . . ?
C3 C4 C9 C8 -178.0(6) . . . . ?
C4 C5 C6 C7 -1.5(9) . . . . ?
C5 C4 C9 N1 -177.8(5) . . . . ?
C5 C4 C9 C8 1.9(8) . . . . ?
C5 C6 C7 C8 0.8(9) . . . . ?
C6 C7 C8 N2 -176.6(6) . . . . ?
C6 C7 C8 C9 1.3(9) . . . . ?
C7 C8 C9 N1 177.1(5) . . . . ?
C7 C8 C9 C4 -2.6(9) . . . . ?
C8 N2 C10 C11 -179.7(6) . . . . ?
C9 N1 C1 C2 -1.0(9) . . . . ?
C9 C4 C5 C6 0.2(9) . . . . ?
C10 N2 C8 C7 1.1(9) . . . . ?
C10 N2 C8 C9 -176.8(5) . . . . ?
C10 C11 C12 C13 180.0(6) . . . . ?
C10 C11 C16 O1 0.0(9) . . . . ?
C10 C11 C16 C15 -179.2(6) . . . . ?
C11 C12 C13 I1 -179.7(5) . . . . ?
C11 C12 C13 C14 -1.1(10) . . . . ?
C12 C11 C16 O1 179.3(6) . . . . ?
C12 C11 C16 C15 0.1(9) . . . . ?
C12 C13 C14 C15 0.8(10) . . . . ?
C13 C14 C15 C16 -0.1(10) . . . . ?
C14 C15 C16 O1 -179.6(6) . . . . ?
C14 C15 C16 C11 -0.4(10) . . . . ?
C16 C11 C12 C13 0.7(9) . . . . ?
C17 C18 C19 C20 176.0(6) . . . . ?
C18 N3 C22 C21 -0.9(9) . . . . ?
C18 N3 C22 C23 -178.5(6) . . . . ?
C18 C19 C20 C21 0.0(10) . . . . ?
C19 C20 C21 C22 1.3(10) . . . . ?
C20 C21 C22 N3 -0.9(9) . . . . ?
C20 C21 C22 C23 176.3(6) . . . . ?
C21 C22 C23 O4 -174.2(6) . . . . ?
C21 C22 C23 O5 5.6(10) . . . . ?
C22 N3 C18 C17 -175.8(5) . . . . ?
C22 N3 C18 C19 2.2(9) . . . . ?

_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 2.508
_oxdiff_exptl_absorpt_empirical_full_min 0.470
####################################################################### 
# 
# 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_rdt117b-150k-new
_database_code_depnum_ccdc_archive 'CCDC 2075296'
loop_
_audit_author_name
_audit_author_address
'David Harding'
;Walailak University
Thailand
;
_audit_update_record             
;
2021-04-05 deposited with the CCDC.	2021-05-14 downloaded from the CCDC.
;
_audit_creation_date             2020-08-24
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H13 Cl Fe N3 O5, C H4 O'
_chemical_formula_sum            'C24 H17 Cl Fe N3 O6'
_chemical_formula_weight         534.70
_chemical_melting_point          ?
_chemical_oxdiff_formula         C24H14ClFeN3O6
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2215(2)
_cell_length_b                   11.9651(3)
_cell_length_c                   12.8982(3)
_cell_angle_alpha                105.940(2)
_cell_angle_beta                 105.557(2)
_cell_angle_gamma                104.264(2)
_cell_volume                     1102.95(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8704
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      67.6030
_cell_measurement_theta_min      3.7890
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.027
_exptl_absorpt_correction_T_max  0.743
_exptl_absorpt_correction_T_min  0.397
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.81a (Rigaku Oxford Diffraction, 2020)
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    1.610
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             546
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 -2 -2 0.0874
-5 1 2 0.0778
0 -5 2 0.0548
0 5 -2 0.0734
0 0 -1 0.0426
0 0 1 0.0056
0 3 -5 0.0577
0 -3 -5 0.0430

_exptl_crystal_size_max          0.177
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.048
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
5.0090 -2.0317 -1.9863 0.0155 -0.1164 -0.9317
-5.0116 1.0344 1.9831 -0.0595 -0.0187 0.9442
-0.0161 -4.9957 1.9834 0.0452 -0.6598 0.0639
0.0161 4.9957 -1.9834 -0.0452 0.6598 -0.0639
0.0015 0.0048 -0.9996 -0.1325 -0.0079 -0.0009
-0.0015 -0.0048 0.9996 0.1325 0.0079 0.0009
0.0155 3.0158 -4.9886 -0.5307 0.3659 -0.0419
-0.0002 -2.9675 -5.0076 -0.7945 -0.4448 0.0326

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16928
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.608
_diffrn_reflns_theta_min         3.821
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -93.00  -9.00   0.50    1.50    --  -40.91 132.00-141.00  168
  2  ω    -96.00 -13.00   0.50    1.50    --  -40.91 137.00  35.00  166
  3  ω     10.00  94.00   0.50    1.50    --   40.91-132.00 148.00  168
  4  ω     13.00  96.00   0.50    1.50    --   40.91-137.00 -28.00  166
  5  ω     74.00 157.00   0.50    5.50    --   96.59 132.00-141.00  166
  6  ω     34.00 121.00   0.50    5.50    --   96.59-137.00 -28.00  174
  7  ω     34.00 116.00   0.50    5.50    --   96.59-132.00 148.00  164
  8  ω     71.00 157.00   0.50    5.50    --   96.59 137.00  35.00  172
  9  ω   -105.00 -29.00   0.50    1.50    --  -40.91 -37.00 150.00  152
 10  ω    -57.00  22.00   0.50    1.50    --  -40.91  50.00-120.00  158
 11  ω   -109.00 -32.00   0.50    1.50    --  -40.91 -25.00  60.00  154
 12  ω   -105.00 -29.00   0.50    1.50    --  -40.91 -37.00-150.00  152
 13  ω    -50.00  27.00   0.50    1.50    --  -40.91  25.00  60.00  154
 14  ω    -23.00  53.00   0.50    1.50    --   40.91 -37.00 -30.00  152
 15  ω    -13.00  77.00   0.50    1.50    --   40.91-104.00-150.00  180
 16  ω    -32.00  63.00   0.50    1.50    --   40.91 -12.00-150.00  190
 17  ω    -23.00  71.00   0.50    1.50    --   40.91 -91.00   0.00  188
 18  ω     29.00 105.00   0.50    1.50    --   40.91  37.00 150.00  152
 19  ω     32.00 109.00   0.50    5.50    --   96.59-117.00   0.00  154
 20  ω     31.00 124.00   0.50    5.50    --   96.59 -86.00 120.00  186
 21  ω     31.00 106.00   0.50    5.50    --   96.59 -33.00  60.00  150
 22  ω     88.00 157.00   0.50    5.50    --   96.59  25.00 -90.00  138
 23  ω     31.00 124.00   0.50    5.50    --   96.59 -86.00 -60.00  186
 24  ω     83.00 157.00   0.50    5.50    --   96.59  17.00-120.00  148
 25  ω     81.00 157.00   0.50    5.50    --   96.59  50.00 -60.00  152
 26  ω     26.00 110.00   0.50    5.50    --   96.59 -17.00 -60.00  168
 27  ω     81.00 157.00   0.50    5.50    --   96.59 117.00-150.00  152
 28  ω     33.00 115.00   0.50    5.50    --   96.59 -59.00 150.00  164
 29  ω     83.00 157.00   0.50    5.50    --   96.59  77.00 120.00  148
 30  ω     33.00 118.00   0.50    5.50    --   96.59 -68.00 -30.00  170
 31  ω     32.00 109.00   0.50    5.50    --   96.59-117.00  90.00  154
 32  ω     34.00 110.00   0.50    5.50    --   96.59 -42.00 150.00  152
 33  ω     81.00 157.00   0.50    5.50    --   96.59  50.00  90.00  152
 34  ω     31.00 106.00   0.50    5.50    --   96.59 -33.00 120.00  150
 35  ω     31.00 124.00   0.50    5.50    --   96.59 -86.00-180.00  186
 36  ω     84.00 157.00   0.50    5.50    --   96.59  96.00  90.00  146
 37  ω     33.00 118.00   0.50    5.50    --   96.59 -68.00 120.00  170
 38  ω     88.00 157.00   0.50    5.50    --   96.59  25.00-180.00  138
 39  ω     34.00 110.00   0.50    5.50    --   96.59 -42.00 -60.00  152
 40  ω   -104.00 -21.00   0.50    1.50    --  -40.91 -63.00   0.00  166
 41  ω   -104.00 -25.00   0.50    1.50    --  -40.91 -50.00  30.00  158
 42  ω   -104.00 -21.00   0.50    1.50    --  -40.91 -63.00 -60.00  166
 43  ω   -104.00 -21.00   0.50    1.50    --  -40.91 -63.00 150.00  166
 44  ω   -104.00 -21.00   0.50    1.50    --  -40.91 -63.00  90.00  166
 45  ω   -104.00 -21.00   0.50    1.50    --  -40.91 -63.00-150.00  166
 46  ω   -104.00 -21.00   0.50    1.50    --  -40.91 -63.00  30.00  166
 47  ω   -104.00 -21.00   0.50    1.50    --  -40.91 -63.00 -90.00  166
 48  ω   -104.00 -21.00   0.50    1.50    --  -40.91 -63.00 -30.00  166
 49  ω   -104.00 -21.00   0.50    1.50    --  -40.91 -63.00  60.00  166
 50  ω   -104.00 -21.00   0.50    1.50    --  -40.91 -63.00-180.00  166
 51  ω   -104.00 -21.00   0.50    1.50    --  -40.91 -63.00 120.00  166
 52  ω     21.00 105.00   0.50    1.50    --   40.91  63.00 -60.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0734253000
_diffrn_orient_matrix_UB_12      0.0434765000
_diffrn_orient_matrix_UB_13      0.1328862000
_diffrn_orient_matrix_UB_21      0.0350690000
_diffrn_orient_matrix_UB_22      0.1353780000
_diffrn_orient_matrix_UB_23      0.0085930000
_diffrn_orient_matrix_UB_31      -0.1906304000
_diffrn_orient_matrix_UB_32      -0.0119518000
_diffrn_orient_matrix_UB_33      0.0005835000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3594
_reflns_number_total             4030
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.000
_refine_diff_density_min         -0.682
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4030
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0755
_refine_ls_restrained_S_all      1.055
_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)+(0.1190P)²+2.2868P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2066
_refine_ls_wR_factor_ref         0.2119
_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,H) groups, All O(H) groups
2. Rigid body (RIGU) restrains
 N3, C18, C19, C20, C21, C22
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C10(H10), C12(H12), C14(H14),
 C15(H15), C19(H19), C20(H20), C21(H21)
3.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
3.c Idealised tetrahedral OH refined as rotating group:
 O6(H6A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.77329(10) 0.70726(6) 0.30657(6) 0.0405(3) Uani 1 1 d . . . . .
Cl1 Cl 1.2967(2) 1.26128(13) 0.25162(16) 0.0726(5) Uani 1 1 d . . . . .
O1 O 0.8116(6) 0.7894(4) 0.2046(3) 0.0728(13) Uani 1 1 d . . . . .
O2 O 0.6431(7) 0.8070(4) 0.3770(3) 0.0678(12) Uani 1 1 d . . . . .
O3 O 0.3753(11) 0.8161(10) 0.3785(5) 0.161(4) Uani 1 1 d . . . . .
O4 O 0.7835(6) 0.5484(4) 0.1991(4) 0.0634(11) Uani 1 1 d . . . . .
O5 O 0.6228(12) 0.3649(5) 0.0574(4) 0.126(3) Uani 1 1 d . . . . .
N1 N 0.8155(5) 0.6298(4) 0.4392(3) 0.0416(9) Uani 1 1 d . . . . .
N2 N 1.0270(5) 0.8281(3) 0.4267(3) 0.0402(8) Uani 1 1 d . . . . .
N3 N 0.5090(5) 0.5965(4) 0.2162(3) 0.0445(8) Uani 1 1 d . . . . .
C1 C 0.7056(8) 0.5272(5) 0.4379(5) 0.0504(12) Uani 1 1 d . . . . .
H1 H 0.596645 0.484976 0.376211 0.061 Uiso 1 1 calc R U . . .
C2 C 0.7473(9) 0.4800(6) 0.5258(6) 0.0594(14) Uani 1 1 d . . . . .
H2 H 0.667738 0.407297 0.521901 0.071 Uiso 1 1 calc R U . . .
C3 C 0.9062(9) 0.5422(5) 0.6175(5) 0.0570(14) Uani 1 1 d . . . . .
H3 H 0.935917 0.511390 0.676119 0.068 Uiso 1 1 calc R U . . .
C4 C 1.0251(8) 0.6529(5) 0.6232(4) 0.0480(12) Uani 1 1 d . . . . .
C5 C 1.1901(9) 0.7227(6) 0.7143(5) 0.0623(16) Uani 1 1 d . . . . .
H5 H 1.224062 0.698175 0.776814 0.075 Uiso 1 1 calc R U . . .
C6 C 1.3005(10) 0.8263(6) 0.7114(5) 0.0691(17) Uani 1 1 d . . . . .
H6 H 1.409074 0.872449 0.772660 0.083 Uiso 1 1 calc R U . . .
C7 C 1.2528(8) 0.8652(5) 0.6164(5) 0.0583(14) Uani 1 1 d . . . . .
H7 H 1.330967 0.935256 0.615081 0.070 Uiso 1 1 calc R U . . .
C8 C 1.0918(7) 0.7995(4) 0.5269(4) 0.0430(10) Uani 1 1 d . . . . .
C9 C 0.9764(7) 0.6934(4) 0.5302(4) 0.0420(10) Uani 1 1 d . . . . .
C10 C 1.1204(6) 0.9248(4) 0.4160(4) 0.0370(9) Uani 1 1 d . . . . .
H10 H 1.229635 0.973020 0.475961 0.044 Uiso 1 1 calc R U . . .
C11 C 1.0741(6) 0.9659(4) 0.3215(4) 0.0374(9) Uani 1 1 d . . . . .
C12 C 1.1912(7) 1.0784(4) 0.3291(4) 0.0450(11) Uani 1 1 d . . . . .
H12 H 1.296178 1.122763 0.393567 0.054 Uiso 1 1 calc R U . . .
C13 C 1.1501(7) 1.1222(4) 0.2416(5) 0.0483(12) Uani 1 1 d . . . . .
C14 C 0.9948(8) 1.0592(5) 0.1449(5) 0.0510(12) Uani 1 1 d . . . . .
H14 H 0.968124 1.092118 0.087615 0.061 Uiso 1 1 calc R U . . .
C15 C 0.8802(8) 0.9482(5) 0.1334(5) 0.0601(14) Uani 1 1 d . . . . .
H15 H 0.776724 0.905617 0.067643 0.072 Uiso 1 1 calc R U . . .
C16 C 0.9172(7) 0.8977(5) 0.2203(4) 0.0488(12) Uani 1 1 d . . . . .
C17 C 0.4732(12) 0.7667(8) 0.3406(6) 0.081(2) Uani 1 1 d . . . . .
C18 C 0.3861(7) 0.6436(7) 0.2402(5) 0.0638(13) Uani 1 1 d . . . . .
C19 C 0.2077(9) 0.5822(10) 0.1782(8) 0.0913(19) Uani 1 1 d . . . . .
H19 H 0.122099 0.616626 0.191757 0.110 Uiso 1 1 calc R U . . .
C20 C 0.1607(11) 0.4727(9) 0.0988(8) 0.102(2) Uani 1 1 d . . . . .
H20 H 0.038582 0.427033 0.060978 0.123 Uiso 1 1 calc R U . . .
C21 C 0.2869(12) 0.4185(7) 0.0662(6) 0.0899(19) Uani 1 1 d . . . . .
H21 H 0.250361 0.342744 0.006438 0.108 Uiso 1 1 calc R U . . .
C22 C 0.4713(9) 0.4898(5) 0.1325(5) 0.0602(12) Uani 1 1 d . . . . .
C23 C 0.6342(11) 0.4618(5) 0.1260(5) 0.0698(19) Uani 1 1 d . . . . .
O6 O 0.2034(8) 0.7781(6) 0.0193(6) 0.1080(19) Uani 1 1 d . . . . .
H6A H 0.246168 0.728959 -0.011104 0.162 Uiso 1 1 calc R U . . .
C24 C 0.3366(12) 0.8795(7) 0.0996(9) 0.108(3) Uani 1 1 d . . . . .
H24A H 0.404482 0.921564 0.063020 0.163 Uiso 1 1 calc R U . . .
H24B H 0.414105 0.856024 0.153234 0.163 Uiso 1 1 calc R U . . .
H24C H 0.286670 0.933589 0.140216 0.163 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
Fe1 O1 1.891(4) . ?
Fe1 O2 1.987(4) . ?
Fe1 O4 2.058(4) . ?
Fe1 N1 2.149(4) . ?
Fe1 N2 2.096(4) . ?
Fe1 N3 2.052(4) . ?
Cl1 C13 1.746(5) . ?
O1 C16 1.297(6) . ?
O2 C17 1.264(9) . ?
O3 C17 1.233(8) . ?
O4 C23 1.298(8) . ?
O5 C23 1.214(7) . ?
N1 C1 1.325(7) . ?
N1 C9 1.374(6) . ?
N2 C8 1.426(6) . ?
N2 C10 1.287(6) . ?
N3 C18 1.336(7) . ?
N3 C22 1.326(7) . ?
C1 H1 0.9300 . ?
C1 C2 1.401(8) . ?
C2 H2 0.9300 . ?
C2 C3 1.367(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.410(8) . ?
C4 C5 1.402(9) . ?
C4 C9 1.410(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.361(10) . ?
C6 H6 0.9300 . ?
C6 C7 1.420(8) . ?
C7 H7 0.9300 . ?
C7 C8 1.368(7) . ?
C8 C9 1.404(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.429(6) . ?
C11 C12 1.409(7) . ?
C11 C16 1.424(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.368(8) . ?
C13 C14 1.382(8) . ?
C14 H14 0.9300 . ?
C14 C15 1.368(8) . ?
C15 H15 0.9300 . ?
C15 C16 1.412(7) . ?
C17 C18 1.515(11) . ?
C18 C19 1.359(9) . ?
C19 H19 0.9300 . ?
C19 C20 1.310(14) . ?
C20 H20 0.9300 . ?
C20 C21 1.445(14) . ?
C21 H21 0.9300 . ?
C21 C22 1.422(10) . ?
C22 C23 1.477(10) . ?
O6 H6A 0.8200 . ?
O6 C24 1.338(9) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
O1 Fe1 O2 97.0(2) . . ?
O1 Fe1 O4 90.84(19) . . ?
O1 Fe1 N1 162.87(18) . . ?
O1 Fe1 N2 88.11(16) . . ?
O1 Fe1 N3 99.74(17) . . ?
O2 Fe1 O4 152.7(2) . . ?
O2 Fe1 N1 92.61(16) . . ?
O2 Fe1 N2 93.63(17) . . ?
O2 Fe1 N3 77.50(19) . . ?
O4 Fe1 N1 86.99(15) . . ?
O4 Fe1 N2 112.84(17) . . ?
N2 Fe1 N1 77.14(15) . . ?
N3 Fe1 O4 75.36(18) . . ?
N3 Fe1 N1 96.15(16) . . ?
N3 Fe1 N2 168.75(16) . . ?
C16 O1 Fe1 133.0(4) . . ?
C17 O2 Fe1 120.1(4) . . ?
C23 O4 Fe1 119.1(4) . . ?
C1 N1 Fe1 126.2(4) . . ?
C1 N1 C9 119.3(4) . . ?
C9 N1 Fe1 114.5(3) . . ?
C8 N2 Fe1 115.7(3) . . ?
C10 N2 Fe1 124.1(3) . . ?
C10 N2 C8 120.2(4) . . ?
C18 N3 Fe1 116.3(4) . . ?
C22 N3 Fe1 118.8(4) . . ?
C22 N3 C18 124.6(5) . . ?
N1 C1 H1 118.7 . . ?
N1 C1 C2 122.5(5) . . ?
C2 C1 H1 118.7 . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.2(5) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0(5) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C9 117.8(5) . . ?
C5 C4 C3 123.6(5) . . ?
C5 C4 C9 118.6(5) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.1(5) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 121.1(6) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 120.0(6) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 N2 125.9(5) . . ?
C7 C8 C9 119.1(5) . . ?
C9 C8 N2 115.0(4) . . ?
N1 C9 C4 121.3(5) . . ?
N1 C9 C8 117.7(4) . . ?
C8 C9 C4 121.1(5) . . ?
N2 C10 H10 116.6 . . ?
N2 C10 C11 126.9(4) . . ?
C11 C10 H10 116.6 . . ?
C12 C11 C10 118.1(4) . . ?
C12 C11 C16 118.9(4) . . ?
C16 C11 C10 123.0(4) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 119.9(5) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 Cl1 119.5(4) . . ?
C12 C13 C14 121.6(5) . . ?
C14 C13 Cl1 118.8(4) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.0(5) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.8(5) . . ?
C16 C15 H15 119.6 . . ?
O1 C16 C11 121.7(4) . . ?
O1 C16 C15 119.6(5) . . ?
C15 C16 C11 118.7(5) . . ?
O2 C17 C18 114.3(5) . . ?
O3 C17 O2 127.2(9) . . ?
O3 C17 C18 118.5(9) . . ?
N3 C18 C17 111.5(5) . . ?
N3 C18 C19 120.9(7) . . ?
C19 C18 C17 127.6(7) . . ?
C18 C19 H19 121.2 . . ?
C20 C19 C18 117.6(9) . . ?
C20 C19 H19 121.2 . . ?
C19 C20 H20 118.0 . . ?
C19 C20 C21 124.0(7) . . ?
C21 C20 H20 118.0 . . ?
C20 C21 H21 122.5 . . ?
C22 C21 C20 115.0(7) . . ?
C22 C21 H21 122.5 . . ?
N3 C22 C21 117.7(7) . . ?
N3 C22 C23 112.6(5) . . ?
C21 C22 C23 129.7(7) . . ?
O4 C23 C22 113.9(5) . . ?
O5 C23 O4 125.2(8) . . ?
O5 C23 C22 120.9(8) . . ?
C24 O6 H6A 109.5 . . ?
O6 C24 H24A 109.5 . . ?
O6 C24 H24B 109.5 . . ?
O6 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Fe1 O1 C16 C11 20.9(9) . . . . ?
Fe1 O1 C16 C15 -161.4(5) . . . . ?
Fe1 O2 C17 O3 177.2(7) . . . . ?
Fe1 O2 C17 C18 -2.1(8) . . . . ?
Fe1 O4 C23 O5 179.1(5) . . . . ?
Fe1 O4 C23 C22 -1.3(6) . . . . ?
Fe1 N1 C1 C2 177.1(4) . . . . ?
Fe1 N1 C9 C4 -179.0(3) . . . . ?
Fe1 N1 C9 C8 0.3(5) . . . . ?
Fe1 N2 C8 C7 -179.9(4) . . . . ?
Fe1 N2 C8 C9 0.5(5) . . . . ?
Fe1 N2 C10 C11 -1.9(6) . . . . ?
Fe1 N3 C18 C17 -6.0(6) . . . . ?
Fe1 N3 C18 C19 174.3(5) . . . . ?
Fe1 N3 C22 C21 -176.0(4) . . . . ?
Fe1 N3 C22 C23 6.0(6) . . . . ?
Cl1 C13 C14 C15 178.2(5) . . . . ?
O2 Fe1 O1 C16 72.6(6) . . . . ?
O2 C17 C18 N3 5.3(8) . . . . ?
O2 C17 C18 C19 -175.0(6) . . . . ?
O3 C17 C18 N3 -174.1(7) . . . . ?
O3 C17 C18 C19 5.6(11) . . . . ?
O4 Fe1 O1 C16 -133.7(6) . . . . ?
N1 Fe1 O1 C16 -51.2(10) . . . . ?
N1 C1 C2 C3 0.7(8) . . . . ?
N2 Fe1 O1 C16 -20.9(6) . . . . ?
N2 C8 C9 N1 -0.5(6) . . . . ?
N2 C8 C9 C4 178.8(4) . . . . ?
N2 C10 C11 C12 176.7(4) . . . . ?
N2 C10 C11 C16 -4.1(7) . . . . ?
N3 Fe1 O1 C16 151.0(6) . . . . ?
N3 C18 C19 C20 3.6(10) . . . . ?
N3 C22 C23 O4 -2.9(7) . . . . ?
N3 C22 C23 O5 176.7(5) . . . . ?
C1 N1 C9 C4 -1.2(7) . . . . ?
C1 N1 C9 C8 178.1(4) . . . . ?
C1 C2 C3 C4 0.6(8) . . . . ?
C2 C3 C4 C5 179.6(5) . . . . ?
C2 C3 C4 C9 -2.1(7) . . . . ?
C3 C4 C5 C6 177.6(5) . . . . ?
C3 C4 C9 N1 2.4(7) . . . . ?
C3 C4 C9 C8 -176.8(4) . . . . ?
C4 C5 C6 C7 -0.7(10) . . . . ?
C5 C4 C9 N1 -179.2(4) . . . . ?
C5 C4 C9 C8 1.5(7) . . . . ?
C5 C6 C7 C8 1.3(10) . . . . ?
C6 C7 C8 N2 179.9(5) . . . . ?
C6 C7 C8 C9 -0.5(8) . . . . ?
C7 C8 C9 N1 179.8(5) . . . . ?
C7 C8 C9 C4 -0.9(7) . . . . ?
C8 N2 C10 C11 -179.9(4) . . . . ?
C9 N1 C1 C2 -0.4(7) . . . . ?
C9 C4 C5 C6 -0.7(8) . . . . ?
C10 N2 C8 C7 -1.8(7) . . . . ?
C10 N2 C8 C9 178.6(4) . . . . ?
C10 C11 C12 C13 -178.8(4) . . . . ?
C10 C11 C16 O1 -4.3(8) . . . . ?
C10 C11 C16 C15 177.9(5) . . . . ?
C11 C12 C13 Cl1 -179.7(3) . . . . ?
C11 C12 C13 C14 0.4(7) . . . . ?
C12 C11 C16 O1 174.8(5) . . . . ?
C12 C11 C16 C15 -2.9(8) . . . . ?
C12 C13 C14 C15 -1.9(8) . . . . ?
C13 C14 C15 C16 0.9(9) . . . . ?
C14 C15 C16 O1 -176.3(6) . . . . ?
C14 C15 C16 C11 1.5(9) . . . . ?
C16 C11 C12 C13 2.0(7) . . . . ?
C17 C18 C19 C20 -176.1(7) . . . . ?
C18 N3 C22 C21 -2.2(8) . . . . ?
C18 N3 C22 C23 179.8(5) . . . . ?
C18 C19 C20 C21 -5.8(12) . . . . ?
C19 C20 C21 C22 3.9(11) . . . . ?
C20 C21 C22 N3 0.2(8) . . . . ?
C20 C21 C22 C23 177.9(6) . . . . ?
C21 C22 C23 O4 179.3(5) . . . . ?
C21 C22 C23 O5 -1.0(10) . . . . ?
C22 N3 C18 C17 -179.9(5) . . . . ?
C22 N3 C18 C19 0.4(9) . . . . ?

_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 2.242
_oxdiff_exptl_absorpt_empirical_full_min 0.581
####################################################################### 
# 
# 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_rdt116-150k
_database_code_depnum_ccdc_archive 'CCDC 2075295'
loop_
_audit_author_name
_audit_author_address
'David Harding'
;Walailak University
Thailand
;
_audit_update_record             
;
2021-04-05 deposited with the CCDC.	2021-05-14 downloaded from the CCDC.
;
_audit_creation_date             2020-08-06
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H13 Br Fe N3 O5, C H4 O'
_chemical_formula_sum            'C24 H17 Br Fe N3 O6'
_chemical_formula_weight         579.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         C24H17FeBrN3O6
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   12.20560(10)
_cell_length_b                   9.30670(10)
_cell_length_c                   18.8067(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.8010(10)
_cell_angle_gamma                90
_cell_volume                     2128.83(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11208
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      68.2200
_cell_measurement_theta_min      4.1540
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.326
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.81a (Rigaku Oxford Diffraction, 2020)
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    1.807
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1164
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 0 2 0.0483
-8 -1 3 0.0354
6 0 -9 0.0111
-1 0 -5 0.0185
0 0 -1 0.0149
0 0 1 0.0131
-4 -5 2 0.1471
5 0 -2 0.0241
0 5 -1 0.2632

_exptl_crystal_size_max          0.451
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.028
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
-4.9994 0.0044 2.0008 -0.1317 -0.6272 0.0013
-7.7189 -0.5502 3.4995 -0.2323 -0.9679 0.0957
5.9190 -0.1217 -8.8417 0.6882 0.7255 -0.0093
-1.0021 0.0009 -4.9970 0.4167 -0.1398 -0.0223
-0.0004 0.0000 -0.9995 0.0820 -0.0027 -0.0042
0.0004 -0.0000 0.9995 -0.0820 0.0027 0.0042
-4.0117 -4.9962 2.0163 -0.0966 -0.5082 0.8289
4.9994 -0.0044 -2.0008 0.1317 0.6272 -0.0013
0.0120 4.9997 -1.0154 0.0405 0.0049 -0.8304

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0782
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17206
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.509
_diffrn_reflns_theta_min         4.164
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -103.00  35.00   0.50    0.80    --  -40.91   4.00 -98.00  276
  2  ω    -21.00 117.00   0.50    0.80    --   40.91   4.00 -98.00  276
  3  ω     21.00 157.00   0.50    2.70    --   96.59  -4.00  84.00  272
  4  ω     35.00 157.00   0.50    2.70    --   96.59   4.00 -98.00  244
  5  ω    -41.00 -15.00   0.50    0.80    --  -40.91 -78.00 175.76   52
  6  ω    -53.00  23.00   0.50    0.80    --  -40.91  37.00 -30.00  152
  7  ω   -104.00 -25.00   0.50    0.80    --  -40.91 -50.00 150.00  158
  8  ω   -117.00  21.00   0.50    0.80    --  -40.91  -4.00  84.00  276
  9  ω     21.00 105.00   0.50    0.80    --   40.91  63.00  30.00  168
 10  ω     15.00  42.00   0.50    0.80    --   40.91  82.00 -28.83   54
 11  ω     15.00  42.00   0.50    0.80    --   40.91  81.00 166.72   54
 12  ω    -13.00  77.00   0.50    0.80    --   40.91-104.00  90.00  180
 13  ω     29.00 105.00   0.50    0.80    --   40.91  37.00 120.00  152
 14  ω    -35.00 103.00   0.50    0.80    --   40.91  -4.00  84.00  276
 15  ω     15.00  42.00   0.50    0.80    --   40.91  81.00   3.32   54
 16  ω     14.00  97.00   0.50    0.80    --   40.91-138.00 -30.00  166
 17  ω     88.00 157.00   0.50    2.70    --   96.59  25.00 -60.00  138
 18  ω     32.00 109.00   0.50    2.70    --   96.59-117.00  30.00  154
 19  ω     32.00 109.00   0.50    2.70    --   96.59-117.00  60.00  154
 20  ω     32.00 109.00   0.50    2.70    --   96.59-117.00 120.00  154
 21  ω     27.00 100.00   0.50    2.70    --   96.59 -96.00 150.00  146
 22  ω     37.00  93.00   0.50    2.70    --   96.59-117.00-180.00  112
 23  ω     29.00 104.00   0.50    2.70    --   96.59 -25.00 150.00  150
 24  ω     31.00 106.00   0.50    2.70    --   96.59 -33.00-120.00  150
 25  ω     64.00 107.00   0.50    2.70    --   96.59 -59.00   0.00   86
 26  ω     89.00 139.00   0.50    2.70    --   96.59  25.00   0.00  100
 27  ω     52.00 109.00   0.50    2.70    --   96.59-117.00 -30.00  114
 28  ω     67.00 104.00   0.50    2.70    --   96.59 -77.00   0.00   74
 29  ω     34.00 103.00   0.50    2.70    --   96.59 -50.00 150.00  138
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0065133000
_diffrn_orient_matrix_UB_12      -0.0085535000
_diffrn_orient_matrix_UB_13      -0.0820799000
_diffrn_orient_matrix_UB_21      0.1264976000
_diffrn_orient_matrix_UB_22      0.0012082000
_diffrn_orient_matrix_UB_23      0.0026172000
_diffrn_orient_matrix_UB_31      0.0012698000
_diffrn_orient_matrix_UB_32      -0.1652456000
_diffrn_orient_matrix_UB_33      0.0041744000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3540
_reflns_number_total             3905
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.920
_refine_diff_density_min         -1.114
_refine_diff_density_rms         0.124
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         3905
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0457
_refine_ls_restrained_S_all      1.056
_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)+(0.0790P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1206
_refine_ls_wR_factor_ref         0.1237
_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,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C10(H10), C12(H12), C14(H14),
 C15(H15), C19(H19), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
2.c Idealised tetrahedral OH refined as rotating group:
 O6(H6A)
;
_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
Br1 Br 0.44639(3) 0.77228(3) 0.76940(2) 0.02084(15) Uani 1 1 d . . . . .
Fe1 Fe 0.73835(4) 0.28645(4) 0.53055(2) 0.01182(16) Uani 1 1 d . . . . .
O1 O 0.75123(16) 0.3953(2) 0.61617(11) 0.0174(4) Uani 1 1 d . . . . .
O2 O 0.83439(16) 0.1294(2) 0.58041(11) 0.0163(4) Uani 1 1 d . . . . .
O3 O 1.00124(17) 0.0271(2) 0.59449(11) 0.0187(5) Uani 1 1 d . . . . .
O4 O 0.71822(16) 0.4520(2) 0.45905(11) 0.0168(4) Uani 1 1 d . . . . .
O5 O 0.78936(18) 0.5808(2) 0.37377(12) 0.0251(5) Uani 1 1 d . . . . .
N1 N 0.6772(2) 0.1267(2) 0.45577(13) 0.0142(5) Uani 1 1 d . . . . .
N2 N 0.5652(2) 0.2971(2) 0.53482(14) 0.0131(5) Uani 1 1 d . . . . .
N3 N 0.8898(2) 0.3078(2) 0.48867(13) 0.0125(5) Uani 1 1 d . . . . .
C1 C 0.7379(2) 0.0366(3) 0.42065(16) 0.0158(6) Uani 1 1 d . . . . .
H1 H 0.814022 0.040553 0.429222 0.019 Uiso 1 1 calc R U . . .
C2 C 0.6920(3) -0.0644(3) 0.37117(16) 0.0190(6) Uani 1 1 d . . . . .
H2 H 0.736990 -0.127973 0.348917 0.023 Uiso 1 1 calc R U . . .
C3 C 0.5811(3) -0.0682(3) 0.35620(16) 0.0179(6) Uani 1 1 d . . . . .
H3 H 0.549932 -0.132765 0.322597 0.022 Uiso 1 1 calc R U . . .
C4 C 0.5132(2) 0.0265(3) 0.39196(15) 0.0150(6) Uani 1 1 d . . . . .
C5 C 0.3974(2) 0.0285(3) 0.38049(16) 0.0163(6) Uani 1 1 d . . . . .
H5 H 0.361721 -0.034427 0.347817 0.020 Uiso 1 1 calc R U . . .
C6 C 0.3377(2) 0.1228(3) 0.41743(16) 0.0169(6) Uani 1 1 d . . . . .
H6 H 0.261654 0.125442 0.408424 0.020 Uiso 1 1 calc R U . . .
C7 C 0.3894(3) 0.2163(3) 0.46895(17) 0.0149(6) Uani 1 1 d . . . . .
H7 H 0.347254 0.279271 0.493706 0.018 Uiso 1 1 calc R U . . .
C8 C 0.5020(3) 0.2144(3) 0.48267(16) 0.0136(6) Uani 1 1 d . . . . .
C9 C 0.5655(2) 0.1206(3) 0.44273(15) 0.0129(6) Uani 1 1 d . . . . .
C10 C 0.5156(2) 0.3848(3) 0.57611(16) 0.0149(6) Uani 1 1 d . . . . .
H10 H 0.439324 0.388482 0.569589 0.018 Uiso 1 1 calc R U . . .
C11 C 0.5677(2) 0.4754(3) 0.63027(16) 0.0145(6) Uani 1 1 d . . . . .
C12 C 0.4987(3) 0.5650(3) 0.66696(16) 0.0166(6) Uani 1 1 d . . . . .
H12 H 0.423235 0.564028 0.655040 0.020 Uiso 1 1 calc R U . . .
C13 C 0.5421(3) 0.6533(3) 0.72001(16) 0.0180(6) Uani 1 1 d . . . . .
C14 C 0.6554(3) 0.6567(3) 0.73905(16) 0.0190(6) Uani 1 1 d . . . . .
H14 H 0.684044 0.716782 0.775474 0.023 Uiso 1 1 calc R U . . .
C15 C 0.7241(3) 0.5698(3) 0.70323(16) 0.0204(6) Uani 1 1 d . . . . .
H15 H 0.799435 0.572409 0.715754 0.024 Uiso 1 1 calc R U . . .
C16 C 0.6828(2) 0.4779(3) 0.64843(15) 0.0141(6) Uani 1 1 d . . . . .
C17 C 0.9364(2) 0.1174(3) 0.56833(15) 0.0144(6) Uani 1 1 d . . . . .
C18 C 0.9728(3) 0.2253(3) 0.51468(17) 0.0133(6) Uani 1 1 d . . . . .
C19 C 1.0763(3) 0.2420(3) 0.49109(17) 0.0167(6) Uani 1 1 d . . . . .
H19 H 1.135283 0.187042 0.510178 0.020 Uiso 1 1 calc R U . . .
C20 C 1.0902(3) 0.3431(3) 0.43813(17) 0.0195(6) Uani 1 1 d . . . . .
H20 H 1.158784 0.355192 0.420889 0.023 Uiso 1 1 calc R U . . .
C21 C 1.0017(2) 0.4262(3) 0.41087(16) 0.0168(6) Uani 1 1 d . . . . .
H21 H 1.009928 0.493409 0.375095 0.020 Uiso 1 1 calc R U . . .
C22 C 0.9016(2) 0.4065(3) 0.43820(15) 0.0143(6) Uani 1 1 d . . . . .
C23 C 0.7961(2) 0.4888(3) 0.42013(16) 0.0159(6) Uani 1 1 d . . . . .
O6 O 0.9949(2) 0.1889(3) 0.28806(15) 0.0411(7) Uani 1 1 d . . . . .
H6A H 1.019720 0.132190 0.318669 0.062 Uiso 1 1 calc R U . . .
C24 C 0.8796(4) 0.1753(5) 0.2791(2) 0.0471(11) Uani 1 1 d . . . . .
H24A H 0.854179 0.198422 0.230753 0.071 Uiso 1 1 calc R U . . .
H24B H 0.846804 0.239895 0.311003 0.071 Uiso 1 1 calc R U . . .
H24C H 0.859172 0.078375 0.289410 0.071 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
Br1 C13 1.907(3) . ?
Fe1 O1 1.898(2) . ?
Fe1 O2 2.051(2) . ?
Fe1 O4 2.046(2) . ?
Fe1 N1 2.137(2) . ?
Fe1 N2 2.123(2) . ?
Fe1 N3 2.078(2) . ?
O1 C16 1.320(3) . ?
O2 C17 1.289(4) . ?
O3 C17 1.229(3) . ?
O4 C23 1.294(4) . ?
O5 C23 1.220(4) . ?
N1 C1 1.331(4) . ?
N1 C9 1.366(4) . ?
N2 C8 1.423(4) . ?
N2 C10 1.309(4) . ?
N3 C18 1.332(4) . ?
N3 C22 1.337(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.406(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.359(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.418(4) . ?
C4 C5 1.412(4) . ?
C4 C9 1.409(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.367(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.411(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.377(4) . ?
C8 C9 1.423(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.430(4) . ?
C11 C12 1.406(4) . ?
C11 C16 1.418(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.365(4) . ?
C13 C14 1.399(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.380(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.400(4) . ?
C17 C18 1.516(4) . ?
C18 C19 1.383(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.391(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.391(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.376(4) . ?
C22 C23 1.512(4) . ?
O6 H6A 0.8200 . ?
O6 C24 1.409(5) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
O1 Fe1 O2 89.37(9) . . ?
O1 Fe1 O4 98.78(9) . . ?
O1 Fe1 N1 158.29(9) . . ?
O1 Fe1 N2 87.42(9) . . ?
O1 Fe1 N3 104.91(9) . . ?
O2 Fe1 N1 87.70(9) . . ?
O2 Fe1 N2 123.25(9) . . ?
O2 Fe1 N3 75.48(9) . . ?
O4 Fe1 O2 150.43(8) . . ?
O4 Fe1 N1 94.30(9) . . ?
O4 Fe1 N2 85.68(9) . . ?
O4 Fe1 N3 74.96(9) . . ?
N2 Fe1 N1 76.33(9) . . ?
N3 Fe1 N1 95.16(9) . . ?
N3 Fe1 N2 158.29(10) . . ?
C16 O1 Fe1 133.67(18) . . ?
C17 O2 Fe1 120.30(18) . . ?
C23 O4 Fe1 121.18(18) . . ?
C1 N1 Fe1 125.9(2) . . ?
C1 N1 C9 118.2(2) . . ?
C9 N1 Fe1 115.82(18) . . ?
C8 N2 Fe1 115.68(18) . . ?
C10 N2 Fe1 124.2(2) . . ?
C10 N2 C8 119.6(3) . . ?
C18 N3 Fe1 118.6(2) . . ?
C18 N3 C22 122.2(3) . . ?
C22 N3 Fe1 119.2(2) . . ?
N1 C1 H1 118.6 . . ?
N1 C1 C2 122.8(3) . . ?
C2 C1 H1 118.6 . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.3(3) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 123.6(3) . . ?
C9 C4 C3 117.3(3) . . ?
C9 C4 C5 119.1(3) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 H6 119.4 . . ?
C5 C6 C7 121.2(3) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.2(3) . . ?
C8 C7 H7 119.9 . . ?
N2 C8 C9 114.0(3) . . ?
C7 C8 N2 126.8(3) . . ?
C7 C8 C9 119.2(3) . . ?
N1 C9 C4 122.5(3) . . ?
N1 C9 C8 117.3(3) . . ?
C4 C9 C8 120.2(3) . . ?
N2 C10 H10 116.9 . . ?
N2 C10 C11 126.2(3) . . ?
C11 C10 H10 116.9 . . ?
C12 C11 C10 116.8(3) . . ?
C12 C11 C16 119.6(3) . . ?
C16 C11 C10 123.6(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 Br1 119.3(2) . . ?
C12 C13 C14 121.0(3) . . ?
C14 C13 Br1 119.7(2) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.3(3) . . ?
C15 C14 H14 120.3 . . ?
C14 C15 H15 119.3 . . ?
C14 C15 C16 121.4(3) . . ?
C16 C15 H15 119.3 . . ?
O1 C16 C11 122.1(3) . . ?
O1 C16 C15 119.4(3) . . ?
C15 C16 C11 118.4(3) . . ?
O2 C17 C18 113.7(2) . . ?
O3 C17 O2 126.0(3) . . ?
O3 C17 C18 120.3(3) . . ?
N3 C18 C17 111.7(3) . . ?
N3 C18 C19 120.3(3) . . ?
C19 C18 C17 128.0(3) . . ?
C18 C19 H19 120.8 . . ?
C18 C19 C20 118.4(3) . . ?
C20 C19 H19 120.8 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.2(3) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 120.9 . . ?
C22 C21 C20 118.3(3) . . ?
C22 C21 H21 120.9 . . ?
N3 C22 C21 120.6(3) . . ?
N3 C22 C23 111.5(2) . . ?
C21 C22 C23 127.9(3) . . ?
O4 C23 C22 113.0(2) . . ?
O5 C23 O4 125.5(3) . . ?
O5 C23 C22 121.4(3) . . ?
C24 O6 H6A 109.5 . . ?
O6 C24 H24A 109.5 . . ?
O6 C24 H24B 109.5 . . ?
O6 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

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
Br1 C13 C14 C15 179.8(2) . . . . ?
Fe1 O1 C16 C11 15.4(4) . . . . ?
Fe1 O1 C16 C15 -165.6(2) . . . . ?
Fe1 O2 C17 O3 -179.3(2) . . . . ?
Fe1 O2 C17 C18 -1.3(3) . . . . ?
Fe1 O4 C23 O5 176.0(2) . . . . ?
Fe1 O4 C23 C22 -4.8(3) . . . . ?
Fe1 N1 C1 C2 -178.9(2) . . . . ?
Fe1 N1 C9 C4 176.4(2) . . . . ?
Fe1 N1 C9 C8 -3.3(3) . . . . ?
Fe1 N2 C8 C7 -171.9(2) . . . . ?
Fe1 N2 C8 C9 9.0(3) . . . . ?
Fe1 N2 C10 C11 -7.5(4) . . . . ?
Fe1 N3 C18 C17 5.0(3) . . . . ?
Fe1 N3 C18 C19 -176.3(2) . . . . ?
Fe1 N3 C22 C21 178.1(2) . . . . ?
Fe1 N3 C22 C23 0.0(3) . . . . ?
O2 Fe1 O1 C16 -142.3(3) . . . . ?
O2 C17 C18 N3 -2.4(3) . . . . ?
O2 C17 C18 C19 179.0(3) . . . . ?
O3 C17 C18 N3 175.8(3) . . . . ?
O3 C17 C18 C19 -2.9(5) . . . . ?
O4 Fe1 O1 C16 66.3(3) . . . . ?
N1 Fe1 O1 C16 -60.1(4) . . . . ?
N1 C1 C2 C3 2.3(4) . . . . ?
N2 Fe1 O1 C16 -19.0(3) . . . . ?
N2 C8 C9 N1 -3.7(4) . . . . ?
N2 C8 C9 C4 176.5(2) . . . . ?
N2 C10 C11 C12 178.0(3) . . . . ?
N2 C10 C11 C16 -2.5(5) . . . . ?
N3 Fe1 O1 C16 142.9(3) . . . . ?
N3 C18 C19 C20 -2.2(4) . . . . ?
N3 C22 C23 O4 2.9(3) . . . . ?
N3 C22 C23 O5 -177.9(3) . . . . ?
C1 N1 C9 C4 -2.4(4) . . . . ?
C1 N1 C9 C8 177.8(3) . . . . ?
C1 C2 C3 C4 -1.8(4) . . . . ?
C2 C3 C4 C5 -179.0(3) . . . . ?
C2 C3 C4 C9 -0.6(4) . . . . ?
C3 C4 C5 C6 179.7(3) . . . . ?
C3 C4 C9 N1 2.8(4) . . . . ?
C3 C4 C9 C8 -177.4(2) . . . . ?
C4 C5 C6 C7 -2.0(4) . . . . ?
C5 C4 C9 N1 -178.7(3) . . . . ?
C5 C4 C9 C8 1.1(4) . . . . ?
C5 C6 C7 C8 0.4(4) . . . . ?
C6 C7 C8 N2 -177.1(3) . . . . ?
C6 C7 C8 C9 2.0(4) . . . . ?
C7 C8 C9 N1 177.1(3) . . . . ?
C7 C8 C9 C4 -2.7(4) . . . . ?
C8 N2 C10 C11 -179.4(3) . . . . ?
C9 N1 C1 C2 -0.2(4) . . . . ?
C9 C4 C5 C6 1.3(4) . . . . ?
C10 N2 C8 C7 0.8(4) . . . . ?
C10 N2 C8 C9 -178.3(2) . . . . ?
C10 C11 C12 C13 179.2(3) . . . . ?
C10 C11 C16 O1 -0.1(4) . . . . ?
C10 C11 C16 C15 -179.1(3) . . . . ?
C11 C12 C13 Br1 -179.4(2) . . . . ?
C11 C12 C13 C14 -0.1(5) . . . . ?
C12 C11 C16 O1 179.4(3) . . . . ?
C12 C11 C16 C15 0.4(4) . . . . ?
C12 C13 C14 C15 0.4(5) . . . . ?
C13 C14 C15 C16 -0.3(5) . . . . ?
C14 C15 C16 O1 -179.1(3) . . . . ?
C14 C15 C16 C11 -0.1(4) . . . . ?
C16 C11 C12 C13 -0.3(4) . . . . ?
C17 C18 C19 C20 176.3(3) . . . . ?
C18 N3 C22 C21 0.1(4) . . . . ?
C18 N3 C22 C23 -178.0(3) . . . . ?
C18 C19 C20 C21 1.0(4) . . . . ?
C19 C20 C21 C22 0.7(4) . . . . ?
C20 C21 C22 N3 -1.3(4) . . . . ?
C20 C21 C22 C23 176.4(3) . . . . ?
C21 C22 C23 O4 -174.9(3) . . . . ?
C21 C22 C23 O5 4.3(5) . . . . ?
C22 N3 C18 C17 -177.0(2) . . . . ?
C22 N3 C18 C19 1.7(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 2.600
_oxdiff_exptl_absorpt_empirical_full_min 0.349
