# Electronic Supplementary Material (ESI) for RSC Medicinal Chemistry.
# 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_bhd_kse9_nm
_database_code_depnum_ccdc_archive 'CCDC 2077461'
loop_
_audit_author_name
_audit_author_address
'Jorg-M. Neudorfl'
;Department Chemie, Organische Chemie, Universitaet zu Koeln
Germany
;
_audit_update_record             
;
2021-04-14 deposited with the CCDC.	2021-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 Fe O7'
_chemical_formula_sum            'C15 H14 Fe O7'
_chemical_formula_weight         362.11

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.1067(3)
_cell_length_b                   12.2043(5)
_cell_length_c                   9.3734(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.110(2)
_cell_angle_gamma                90
_cell_volume                     788.45(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8640
_cell_measurement_theta_min      4.86
_cell_measurement_theta_max      71.74
_exptl_crystal_description       'Irregular block'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_F_000             372
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    7.987
_shelx_estimated_absorpt_T_min   0.380
_shelx_estimated_absorpt_T_max   0.796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4517
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro focus'
_diffrn_detector_type            'Bruker PhotonIII M14'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14895
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.865
_diffrn_reflns_theta_max         71.892
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3057
_reflns_number_gt                2880
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.905
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_computing_data_collection       'Bruker APEX 3'
_computing_cell_refinement       'Bruker APEX 3'
_computing_data_reduction        'Bruker APEX 3'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_computing_structure_refinement  
;
SHELXL-2014/7 (Sheldrick, 2014)
SHELXLE (C. B. Huebschle 2016)'
;
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2015)'


_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.

 

 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0468P)²+0.8031P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.467(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3057
_refine_ls_number_parameters     210
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1039
_refine_ls_wR_factor_gt          0.1008
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.21875(10) 0.47721(7) 0.53851(8) 0.0244(2) Uani 1 1 d . . . . .
O1 O 0.2566(5) 0.5317(4) 0.2272(4) 0.0290(8) Uani 1 1 d . . . . .
O2 O 0.5749(5) 0.4957(4) 0.3187(4) 0.0312(10) Uani 1 1 d . . . . .
O3 O 0.8610(5) 0.5423(3) -0.0053(4) 0.0271(8) Uani 1 1 d . . . . .
O4 O 0.5787(7) 0.6247(4) -0.0073(6) 0.0455(12) Uani 1 1 d . . . . .
O5 O 0.2125(7) 0.2810(4) 0.3568(5) 0.0455(12) Uani 1 1 d . . . . .
O6 O 0.0726(7) 0.3604(4) 0.7655(5) 0.0489(12) Uani 1 1 d . . . . .
O7 O 0.6365(5) 0.4970(4) 0.6709(4) 0.0374(11) Uani 1 1 d . . . . .
C1 C 0.2303(9) 0.5777(5) 0.3611(7) 0.0299(13) Uani 1 1 d . . . . .
C2 C 0.0369(8) 0.5616(5) 0.3730(7) 0.0305(12) Uani 1 1 d . . . . .
H2 H -0.0644 0.5249 0.2947 0.037 Uiso 1 1 calc R U . . .
C3 C 0.0041(10) 0.5936(5) 0.5097(7) 0.0347(13) Uani 1 1 d . . . . .
H3 H -0.1218 0.5815 0.5370 0.042 Uiso 1 1 calc R U . . .
C4 C 0.1731(9) 0.6375(5) 0.6097(7) 0.0335(13) Uani 1 1 d . . . . .
H4 H 0.1656 0.6444 0.7145 0.040 Uiso 1 1 calc R U . . .
C5 C 0.3040(10) 0.7181(5) 0.5598(8) 0.0417(15) Uani 1 1 d . . . . .
H5A H 0.4304 0.7215 0.6331 0.050 Uiso 1 1 calc R U . . .
H5AB H 0.2449 0.7920 0.5516 0.050 Uiso 1 1 calc R U . . .
C6 C 0.3363(9) 0.6825(5) 0.4070(7) 0.0336(13) Uani 1 1 d . . . . .
H6A H 0.2874 0.7401 0.3329 0.040 Uiso 1 1 calc R U . . .
H6AB H 0.4765 0.6722 0.4145 0.040 Uiso 1 1 calc R U . . .
C7 C 0.4314(7) 0.4902(6) 0.2205(5) 0.0298(12) Uani 1 1 d . . . . .
C8 C 0.4153(8) 0.4330(6) 0.0747(6) 0.0355(13) Uani 1 1 d . . . . .
H8A H 0.3729 0.3564 0.0821 0.043 Uiso 1 1 calc R U . . .
H8AB H 0.3154 0.4702 -0.0023 0.043 Uiso 1 1 calc R U . . .
C9 C 0.6052(8) 0.4333(5) 0.0305(6) 0.0262(12) Uani 1 1 d . . . . .
C10 C 0.6934(10) 0.3422(5) 0.0089(9) 0.0443(17) Uani 1 1 d . . . . .
H10A H 0.8080 0.3453 -0.0261 0.053 Uiso 1 1 calc R U . . .
H10B H 0.6424 0.2733 0.0282 0.053 Uiso 1 1 calc R U . . .
C11 C 0.6749(9) 0.5437(5) 0.0032(6) 0.0282(12) Uani 1 1 d . . . . .
C12 C 0.9408(10) 0.6458(5) -0.0312(7) 0.0382(14) Uani 1 1 d . . . . .
H12A H 0.8727 0.6732 -0.1284 0.057 Uiso 1 1 calc R U . . .
H12B H 1.0790 0.6371 -0.0276 0.057 Uiso 1 1 calc R U . . .
H12C H 0.9254 0.6981 0.0444 0.057 Uiso 1 1 calc R U . . .
C13 C 0.2128(9) 0.3571(5) 0.4311(7) 0.0337(13) Uani 1 1 d . . . . .
C14 C 0.1312(9) 0.4077(6) 0.6774(7) 0.0368(14) Uani 1 1 d . . . . .
C15 C 0.4738(8) 0.4876(6) 0.6199(5) 0.0310(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 C13 1.773(6) . ?
Fe1 C14 1.788(7) . ?
Fe1 C15 1.792(5) . ?
Fe1 C2 2.039(6) . ?
Fe1 C3 2.053(6) . ?
Fe1 C1 2.083(6) . ?
Fe1 C4 2.118(6) . ?
O1 C7 1.357(7) . ?
O1 C1 1.428(7) . ?
O2 C7 1.198(6) . ?
O3 C11 1.345(7) . ?
O3 C12 1.430(7) . ?
O4 C11 1.192(7) . ?
O5 C13 1.160(8) . ?
O6 C14 1.164(8) . ?
O7 C15 1.144(6) . ?
C1 C2 1.420(8) . ?
C1 C6 1.493(8) . ?
C2 C3 1.412(8) . ?
C2 H2 1.0000 . ?
C3 C4 1.435(9) . ?
C3 H3 1.0000 . ?
C4 C5 1.505(9) . ?
C4 H4 1.0000 . ?
C5 C6 1.566(9) . ?
C5 H5A 0.9900 . ?
C5 H5AB 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6AB 0.9900 . ?
C7 C8 1.514(8) . ?
C8 C9 1.505(8) . ?
C8 H8A 0.9900 . ?
C8 H8AB 0.9900 . ?
C9 C10 1.316(9) . ?
C9 C11 1.479(8) . ?
C10 H10A 0.9500 . ?
C10 H10B 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 Fe1 C14 93.3(3) . . ?
C13 Fe1 C15 100.5(3) . . ?
C14 Fe1 C15 102.7(3) . . ?
C13 Fe1 C2 93.6(3) . . ?
C14 Fe1 C2 121.7(3) . . ?
C15 Fe1 C2 132.5(3) . . ?
C13 Fe1 C3 125.7(3) . . ?
C14 Fe1 C3 92.6(3) . . ?
C15 Fe1 C3 130.5(3) . . ?
C2 Fe1 C3 40.4(2) . . ?
C13 Fe1 C1 91.9(3) . . ?
C14 Fe1 C1 161.6(3) . . ?
C15 Fe1 C1 93.7(3) . . ?
C2 Fe1 C1 40.3(2) . . ?
C3 Fe1 C1 70.2(2) . . ?
C13 Fe1 C4 163.5(3) . . ?
C14 Fe1 C4 95.8(3) . . ?
C15 Fe1 C4 91.0(3) . . ?
C2 Fe1 C4 69.9(3) . . ?
C3 Fe1 C4 40.2(3) . . ?
C1 Fe1 C4 75.3(2) . . ?
C7 O1 C1 120.3(4) . . ?
C11 O3 C12 115.8(5) . . ?
C2 C1 O1 110.6(5) . . ?
C2 C1 C6 121.7(5) . . ?
O1 C1 C6 115.1(5) . . ?
C2 C1 Fe1 68.2(3) . . ?
O1 C1 Fe1 120.6(4) . . ?
C6 C1 Fe1 112.9(4) . . ?
C3 C2 C1 114.2(5) . . ?
C3 C2 Fe1 70.3(4) . . ?
C1 C2 Fe1 71.5(3) . . ?
C3 C2 H2 122.8 . . ?
C1 C2 H2 122.8 . . ?
Fe1 C2 H2 122.8 . . ?
C2 C3 C4 113.5(5) . . ?
C2 C3 Fe1 69.3(3) . . ?
C4 C3 Fe1 72.3(4) . . ?
C2 C3 H3 123.2 . . ?
C4 C3 H3 123.2 . . ?
Fe1 C3 H3 123.2 . . ?
C3 C4 C5 121.6(6) . . ?
C3 C4 Fe1 67.5(3) . . ?
C5 C4 Fe1 110.6(4) . . ?
C3 C4 H4 115.9 . . ?
C5 C4 H4 115.9 . . ?
Fe1 C4 H4 115.9 . . ?
C4 C5 C6 110.0(5) . . ?
C4 C5 H5A 109.7 . . ?
C6 C5 H5A 109.7 . . ?
C4 C5 H5AB 109.7 . . ?
C6 C5 H5AB 109.7 . . ?
H5A C5 H5AB 108.2 . . ?
C1 C6 C5 109.0(5) . . ?
C1 C6 H6A 109.9 . . ?
C5 C6 H6A 109.9 . . ?
C1 C6 H6AB 109.9 . . ?
C5 C6 H6AB 109.9 . . ?
H6A C6 H6AB 108.3 . . ?
O2 C7 O1 124.2(5) . . ?
O2 C7 C8 125.6(5) . . ?
O1 C7 C8 110.2(4) . . ?
C9 C8 C7 111.8(5) . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8AB 109.3 . . ?
C7 C8 H8AB 109.3 . . ?
H8A C8 H8AB 107.9 . . ?
C10 C9 C11 123.4(5) . . ?
C10 C9 C8 122.2(6) . . ?
C11 C9 C8 114.2(5) . . ?
C9 C10 H10A 120.0 . . ?
C9 C10 H10B 120.0 . . ?
H10A C10 H10B 120.0 . . ?
O4 C11 O3 123.9(6) . . ?
O4 C11 C9 124.1(6) . . ?
O3 C11 C9 112.0(5) . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O5 C13 Fe1 177.1(6) . . ?
O6 C14 Fe1 178.4(6) . . ?
O7 C15 Fe1 178.3(7) . . ?

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
C7 O1 C1 C2 -148.5(5) . . . . ?
C7 O1 C1 C6 68.7(7) . . . . ?
C7 O1 C1 Fe1 -72.4(6) . . . . ?
O1 C1 C2 C3 173.2(5) . . . . ?
C6 C1 C2 C3 -46.8(8) . . . . ?
Fe1 C1 C2 C3 57.4(5) . . . . ?
O1 C1 C2 Fe1 115.8(4) . . . . ?
C6 C1 C2 Fe1 -104.2(6) . . . . ?
C1 C2 C3 C4 0.7(8) . . . . ?
Fe1 C2 C3 C4 58.8(5) . . . . ?
C1 C2 C3 Fe1 -58.0(5) . . . . ?
C2 C3 C4 C5 44.0(8) . . . . ?
Fe1 C3 C4 C5 101.1(5) . . . . ?
C2 C3 C4 Fe1 -57.1(5) . . . . ?
C3 C4 C5 C6 -42.0(8) . . . . ?
Fe1 C4 C5 C6 33.5(7) . . . . ?
C2 C1 C6 C5 45.4(8) . . . . ?
O1 C1 C6 C5 -176.3(5) . . . . ?
Fe1 C1 C6 C5 -32.3(6) . . . . ?
C4 C5 C6 C1 -1.5(8) . . . . ?
C1 O1 C7 O2 -5.4(10) . . . . ?
C1 O1 C7 C8 172.4(5) . . . . ?
O2 C7 C8 C9 -29.3(10) . . . . ?
O1 C7 C8 C9 152.9(5) . . . . ?
C7 C8 C9 C10 120.3(7) . . . . ?
C7 C8 C9 C11 -64.0(7) . . . . ?
C12 O3 C11 O4 -1.2(8) . . . . ?
C12 O3 C11 C9 -179.9(5) . . . . ?
C10 C9 C11 O4 163.9(7) . . . . ?
C8 C9 C11 O4 -11.7(8) . . . . ?
C10 C9 C11 O3 -17.5(9) . . . . ?
C8 C9 C11 O3 166.9(4) . . . . ?

_refine_diff_density_max         1.104
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_bhd_kse10n
_database_code_depnum_ccdc_archive 'CCDC 2077462'
loop_
_audit_author_name
_audit_author_address
'Jorg-M. Neudorfl'
;Department Chemie, Organische Chemie, Universitaet zu Koeln
Germany
;
_audit_update_record             
;
2021-04-14 deposited with the CCDC.	2021-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 Fe O7'
_chemical_formula_sum            'C15 H14 Fe O7'
_chemical_formula_weight         362.11

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'
O O 0.0492 0.0322 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.3484(2)
_cell_length_b                   7.47810(10)
_cell_length_c                   36.7370(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3117.67(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9990
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      72.29
_exptl_crystal_description       irregular_platelet
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    8.079
_shelx_estimated_absorpt_T_min   0.377
_shelx_estimated_absorpt_T_max   0.794
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3992
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro focus'
_diffrn_detector_type            'Bruker PhotonIII M14'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'phi / omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33111
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_theta_min         4.580
_diffrn_reflns_theta_max         72.285
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3074
_reflns_number_gt                2919
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX 3'
_computing_cell_refinement       'Bruker APEX 3'
_computing_data_reduction        'Bruker APEX 3'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_computing_structure_refinement  
;
SHELXL-2014/7 (Sheldrick, 2014)
SHELXLE (C. B. Huebschle 2016)'
;
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2015)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0427P)²+3.7377P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3074
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.0945
_refine_ls_wR_factor_gt          0.0935
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.55946(3) 0.68238(5) 0.42855(2) 0.01732(12) Uani 1 1 d . . . . .
O1 O 0.76864(15) 0.5948(3) 0.38523(6) 0.0391(5) Uani 1 1 d . . . . .
O2 O 0.69472(18) 0.8615(3) 0.48640(6) 0.0442(5) Uani 1 1 d . . . . .
O3 O 0.51288(17) 0.3310(2) 0.46105(5) 0.0314(4) Uani 1 1 d . . . . .
O4 O 0.49548(13) 0.5819(2) 0.35017(4) 0.0198(3) Uani 1 1 d . . . . .
O5 O 0.49468(15) 0.2930(2) 0.36910(5) 0.0259(4) Uani 1 1 d . . . . .
O6 O 0.37927(14) 0.1680(2) 0.28875(5) 0.0283(4) Uani 1 1 d . . . . .
O7 O 0.47371(14) -0.0922(2) 0.29633(5) 0.0240(3) Uani 1 1 d . . . . .
C1 C 0.44978(18) 0.6490(3) 0.38363(6) 0.0181(4) Uani 1 1 d . . . . .
C2 C 0.48189(19) 0.8326(3) 0.38841(6) 0.0201(4) Uani 1 1 d . . . . .
H2 H 0.5276 0.9024 0.3700 0.024 Uiso 1 1 calc R U . . .
C3 C 0.45037(19) 0.9008(3) 0.42283(7) 0.0221(5) Uani 1 1 d . . . . .
H3 H 0.4739 1.0231 0.4310 0.027 Uiso 1 1 calc R U . . .
C4 C 0.39325(19) 0.7764(3) 0.44644(6) 0.0217(4) Uani 1 1 d . . . . .
H4 H 0.3873 0.8114 0.4726 0.026 Uiso 1 1 calc R U . . .
C5 C 0.2984(2) 0.6530(3) 0.43220(6) 0.0222(5) Uani 1 1 d . . . . .
H5A H 0.2220 0.7169 0.4320 0.027 Uiso 1 1 calc R U . . .
H5AB H 0.2909 0.5488 0.4486 0.027 Uiso 1 1 calc R U . . .
C6 C 0.32689(18) 0.5871(3) 0.39329(6) 0.0210(4) Uani 1 1 d . . . . .
H6A H 0.3225 0.4550 0.3923 0.025 Uiso 1 1 calc R U . . .
H6AB H 0.2692 0.6367 0.3758 0.025 Uiso 1 1 calc R U . . .
C7 C 0.6888(2) 0.6319(3) 0.40258(7) 0.0244(5) Uani 1 1 d . . . . .
C8 C 0.6425(2) 0.7894(4) 0.46420(7) 0.0283(5) Uani 1 1 d . . . . .
C9 C 0.5323(2) 0.4665(3) 0.44838(6) 0.0237(5) Uani 1 1 d . . . . .
C10 C 0.51790(19) 0.4047(3) 0.34659(6) 0.0191(4) Uani 1 1 d . . . . .
C11 C 0.57657(18) 0.3651(3) 0.31104(6) 0.0188(4) Uani 1 1 d . . . . .
C12 C 0.58690(19) 0.1691(3) 0.30288(6) 0.0192(4) Uani 1 1 d . . . . .
H12A H 0.6242 0.1077 0.3238 0.023 Uiso 1 1 calc R U . . .
H12B H 0.6382 0.1521 0.2814 0.023 Uiso 1 1 calc R U . . .
C13 C 0.46762(19) 0.0860(3) 0.29552(6) 0.0194(4) Uani 1 1 d . . . . .
C14 C 0.6157(2) 0.4923(3) 0.28899(6) 0.0254(5) Uani 1 1 d . . . . .
H14A H 0.6070 0.6145 0.2956 0.030 Uiso 1 1 calc R U . . .
H14B H 0.6525 0.4613 0.2666 0.030 Uiso 1 1 calc R U . . .
C15 C 0.3630(2) -0.1835(3) 0.28988(8) 0.0307(5) Uani 1 1 d . . . . .
H15A H 0.3340 -0.1538 0.2655 0.046 Uiso 1 1 calc R U . . .
H15B H 0.3050 -0.1454 0.3081 0.046 Uiso 1 1 calc R U . . .
H15C H 0.3750 -0.3130 0.2917 0.046 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 C7 1.791(2) . ?
Fe1 C9 1.797(3) . ?
Fe1 C8 1.801(3) . ?
Fe1 C2 2.052(2) . ?
Fe1 C3 2.060(2) . ?
Fe1 C1 2.082(2) . ?
Fe1 C4 2.118(2) . ?
O1 C7 1.142(3) . ?
O2 C8 1.144(3) . ?
O3 C9 1.137(3) . ?
O4 C10 1.356(3) . ?
O4 C1 1.425(3) . ?
O5 C10 1.205(3) . ?
O6 C13 1.201(3) . ?
O7 C13 1.335(3) . ?
O7 C15 1.450(3) . ?
C1 C2 1.431(3) . ?
C1 C6 1.512(3) . ?
C2 C3 1.410(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.427(3) . ?
C3 H3 1.0000 . ?
C4 C5 1.511(3) . ?
C4 H4 1.0000 . ?
C5 C6 1.546(3) . ?
C5 H5A 0.9900 . ?
C5 H5AB 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6AB 0.9900 . ?
C10 C11 1.496(3) . ?
C11 C14 1.326(3) . ?
C11 C12 1.500(3) . ?
C12 C13 1.514(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C14 H14A 0.9500 . ?
C14 H14B 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 Fe1 C9 99.63(11) . . ?
C7 Fe1 C8 93.00(11) . . ?
C9 Fe1 C8 101.19(11) . . ?
C7 Fe1 C2 94.82(10) . . ?
C9 Fe1 C2 135.17(10) . . ?
C8 Fe1 C2 120.24(11) . . ?
C7 Fe1 C3 127.24(10) . . ?
C9 Fe1 C3 130.56(10) . . ?
C8 Fe1 C3 92.07(11) . . ?
C2 Fe1 C3 40.09(9) . . ?
C7 Fe1 C1 92.43(10) . . ?
C9 Fe1 C1 96.37(10) . . ?
C8 Fe1 C1 160.46(11) . . ?
C2 Fe1 C1 40.51(8) . . ?
C3 Fe1 C1 69.82(9) . . ?
C7 Fe1 C4 164.87(10) . . ?
C9 Fe1 C4 91.13(10) . . ?
C8 Fe1 C4 95.31(10) . . ?
C2 Fe1 C4 70.07(9) . . ?
C3 Fe1 C4 39.92(9) . . ?
C1 Fe1 C4 75.72(8) . . ?
C10 O4 C1 119.72(17) . . ?
C13 O7 C15 114.92(18) . . ?
O4 C1 C2 110.52(18) . . ?
O4 C1 C6 115.51(18) . . ?
C2 C1 C6 119.98(19) . . ?
O4 C1 Fe1 120.55(14) . . ?
C2 C1 Fe1 68.62(12) . . ?
C6 C1 Fe1 113.71(15) . . ?
C3 C2 C1 113.1(2) . . ?
C3 C2 Fe1 70.26(13) . . ?
C1 C2 Fe1 70.87(12) . . ?
C3 C2 H2 123.4 . . ?
C1 C2 H2 123.4 . . ?
Fe1 C2 H2 123.4 . . ?
C2 C3 C4 115.1(2) . . ?
C2 C3 Fe1 69.65(13) . . ?
C4 C3 Fe1 72.21(13) . . ?
C2 C3 H3 122.3 . . ?
C4 C3 H3 122.3 . . ?
Fe1 C3 H3 122.3 . . ?
C3 C4 C5 120.7(2) . . ?
C3 C4 Fe1 67.87(12) . . ?
C5 C4 Fe1 108.91(14) . . ?
C3 C4 H4 116.4 . . ?
C5 C4 H4 116.4 . . ?
Fe1 C4 H4 116.4 . . ?
C4 C5 C6 111.47(18) . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5AB 109.3 . . ?
C6 C5 H5AB 109.3 . . ?
H5A C5 H5AB 108.0 . . ?
C1 C6 C5 108.19(18) . . ?
C1 C6 H6A 110.1 . . ?
C5 C6 H6A 110.1 . . ?
C1 C6 H6AB 110.1 . . ?
C5 C6 H6AB 110.1 . . ?
H6A C6 H6AB 108.4 . . ?
O1 C7 Fe1 177.2(2) . . ?
O2 C8 Fe1 178.2(3) . . ?
O3 C9 Fe1 178.6(2) . . ?
O5 C10 O4 124.8(2) . . ?
O5 C10 C11 124.0(2) . . ?
O4 C10 C11 111.23(19) . . ?
C14 C11 C10 122.7(2) . . ?
C14 C11 C12 123.5(2) . . ?
C10 C11 C12 113.78(19) . . ?
C11 C12 C13 111.52(18) . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
O6 C13 O7 123.9(2) . . ?
O6 C13 C12 125.0(2) . . ?
O7 C13 C12 111.07(18) . . ?
C11 C14 H14A 120.0 . . ?
C11 C14 H14B 120.0 . . ?
H14A C14 H14B 120.0 . . ?
O7 C15 H15A 109.5 . . ?
O7 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O7 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C10 O4 C1 C2 153.50(18) . . . . ?
C10 O4 C1 C6 -66.2(2) . . . . ?
C10 O4 C1 Fe1 76.9(2) . . . . ?
O4 C1 C2 C3 -173.40(18) . . . . ?
C6 C1 C2 C3 48.3(3) . . . . ?
Fe1 C1 C2 C3 -57.54(17) . . . . ?
O4 C1 C2 Fe1 -115.86(16) . . . . ?
C6 C1 C2 Fe1 105.83(19) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
Fe1 C2 C3 C4 -57.73(18) . . . . ?
C1 C2 C3 Fe1 57.88(16) . . . . ?
C2 C3 C4 C5 -43.1(3) . . . . ?
Fe1 C3 C4 C5 -99.51(19) . . . . ?
C2 C3 C4 Fe1 56.37(17) . . . . ?
C3 C4 C5 C6 37.3(3) . . . . ?
Fe1 C4 C5 C6 -37.6(2) . . . . ?
O4 C1 C6 C5 173.02(18) . . . . ?
C2 C1 C6 C5 -50.6(3) . . . . ?
Fe1 C1 C6 C5 27.5(2) . . . . ?
C4 C5 C6 C1 7.3(3) . . . . ?
C1 O4 C10 O5 5.3(3) . . . . ?
C1 O4 C10 C11 -174.19(17) . . . . ?
O5 C10 C11 C14 -170.5(2) . . . . ?
O4 C10 C11 C14 9.0(3) . . . . ?
O5 C10 C11 C12 9.4(3) . . . . ?
O4 C10 C11 C12 -171.08(17) . . . . ?
C14 C11 C12 C13 -111.3(2) . . . . ?
C10 C11 C12 C13 68.8(2) . . . . ?
C15 O7 C13 O6 -2.5(3) . . . . ?
C15 O7 C13 C12 179.46(19) . . . . ?
C11 C12 C13 O6 15.9(3) . . . . ?
C11 C12 C13 O7 -166.13(18) . . . . ?

_refine_diff_density_max         1.342
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.059

