# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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_FO6491_2
_database_code_depnum_ccdc_archive 'CCDC 2169541'
loop_
_audit_author_name
_audit_author_address
'Helmar Goerls'
;University Jena
Germany
;
_audit_update_record             
;
2022-04-29 deposited with the CCDC.	2022-06-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H10 Fe O3 S2'
_chemical_formula_sum            'C16 H10 Fe O3 S2'
_chemical_formula_weight         370.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.4288(4)
_cell_length_b                   8.8456(5)
_cell_length_c                   14.0419(9)
_cell_angle_alpha                105.769(3)
_cell_angle_beta                 99.980(3)
_cell_angle_gamma                99.222(3)
_cell_volume                     738.50(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    6988
_cell_measurement_theta_min      2.452
_cell_measurement_theta_max      27.483

_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.088
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.044
_exptl_absorpt_coefficient_mu    1.311
_shelx_estimated_absorpt_T_min   0.893
_shelx_estimated_absorpt_T_max   0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6271
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   micro-source
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi- + omega-scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6988
_diffrn_reflns_av_unetI/netI     0.0750
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.452
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3352
_reflns_number_gt                2635
_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       COLLECT
_computing_cell_refinement       DENZO
_computing_data_reduction        DENZO
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.1126P)²+4.5453P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3352
_refine_ls_number_parameters     215
_refine_ls_number_restraints     144
_refine_ls_R_factor_all          0.1115
_refine_ls_R_factor_gt           0.0878
_refine_ls_wR_factor_ref         0.2348
_refine_ls_wR_factor_gt          0.2155
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.075
_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
S2 S 0.8005(9) 0.2137(6) 0.5529(4) 0.0468(10) Uani 0.583(7) 1 d D U P A 1
C13 C 0.591(2) 0.1766(16) 0.5988(11) 0.032(3) Uani 0.583(7) 1 d D U P A 1
H13 H 0.588000 0.129606 0.651996 0.038 Uiso 0.583(7) 1 calc R U P A 1
C12 C 0.421(3) 0.2216(18) 0.5512(11) 0.031(2) Uani 0.583(7) 1 d D U P A 1
H12 H 0.280579 0.206574 0.564668 0.037 Uiso 0.583(7) 1 calc R U P A 1
C11 C 0.478(3) 0.292(2) 0.4808(14) 0.038(3) Uani 0.583(7) 1 d D U P A 1
H11 H 0.385321 0.339374 0.443322 0.045 Uiso 0.583(7) 1 calc R U P A 1
C10 C 0.682(3) 0.286(4) 0.4710(17) 0.0200(14) Uani 0.583(7) 1 d D U P A 1
S2A S 0.4245(12) 0.2715(10) 0.4638(6) 0.0468(10) Uani 0.417(7) 1 d D U P A 2
C13A C 0.442(4) 0.210(3) 0.5642(15) 0.032(3) Uani 0.417(7) 1 d D U P A 2
H13A H 0.324062 0.185998 0.594196 0.038 Uiso 0.417(7) 1 calc R U P A 2
C12A C 0.647(3) 0.200(2) 0.5983(16) 0.031(2) Uani 0.417(7) 1 d D U P A 2
H12A H 0.691233 0.165193 0.655526 0.037 Uiso 0.417(7) 1 calc R U P A 2
C11A C 0.783(4) 0.244(4) 0.5418(19) 0.038(3) Uani 0.417(7) 1 d D U P A 2
H11A H 0.934159 0.246646 0.555814 0.045 Uiso 0.417(7) 1 calc R U P A 2
C10A C 0.678(4) 0.282(5) 0.464(2) 0.0200(14) Uani 0.417(7) 1 d D U P A 2
Fe1 Fe 0.76465(14) 0.20163(10) 0.24364(6) 0.0172(3) Uani 1 1 d . . . . .
S1 S 1.0874(2) 0.37952(19) 0.26598(13) 0.0239(4) Uani 1 1 d . . . . .
O1 O 0.7542(9) 0.1006(6) 0.0243(4) 0.0347(12) Uani 1 1 d . . . . .
O2 O 0.3075(8) 0.0483(6) 0.2078(4) 0.0310(11) Uani 1 1 d . . . . .
O3 O 0.9448(8) -0.0450(6) 0.3162(4) 0.0311(11) Uani 1 1 d . . . . .
C1 C 0.5796(10) 0.5849(7) 0.1809(5) 0.0219(12) Uani 1 1 d . . . . .
H1A H 0.481535 0.555848 0.219629 0.026 Uiso 1 1 calc R U . . .
C2 C 0.5245(11) 0.6715(7) 0.1153(5) 0.0255(14) Uani 1 1 d . . . . .
H2A H 0.388417 0.701416 0.109113 0.031 Uiso 1 1 calc R U . . .
C3 C 0.6662(11) 0.7148(7) 0.0587(5) 0.0249(13) Uani 1 1 d . . . . .
H3A H 0.627566 0.773229 0.013203 0.030 Uiso 1 1 calc R U . . .
C4 C 0.8633(11) 0.6725(9) 0.0689(6) 0.0310(15) Uani 1 1 d . . . . .
H4A H 0.961240 0.702270 0.030329 0.037 Uiso 1 1 calc R U . . .
C5 C 0.9212(11) 0.5868(8) 0.1348(6) 0.0302(15) Uani 1 1 d . . . . .
H5A H 1.059235 0.560164 0.141817 0.036 Uiso 1 1 calc R U . . .
C6 C 0.7802(10) 0.5399(7) 0.1902(5) 0.0190(12) Uani 1 1 d . . . . .
C7 C 0.8472(10) 0.4498(7) 0.2632(4) 0.0197(12) Uani 1 1 d . . . . .
C8 C 0.7295(10) 0.4207(7) 0.3349(4) 0.0200(12) Uani 1 1 d . . . . .
H8A H 0.598439 0.456480 0.338027 0.024 Uiso 1 1 calc R U . . .
C9 C 0.8073(11) 0.3376(7) 0.4025(5) 0.0218(13) Uani 1 1 d . . . . .
H9A H 0.946890 0.314539 0.403611 0.026 Uiso 0.583(7) 1 calc R U P A 1
H9B H 0.949497 0.318724 0.406636 0.026 Uiso 0.417(7) 1 calc R U P A 2
C14 C 0.7554(11) 0.1396(7) 0.1087(5) 0.0233(13) Uani 1 1 d . . . . .
C15 C 0.4853(10) 0.1090(8) 0.2231(4) 0.0223(13) Uani 1 1 d . . . . .
C16 C 0.8726(9) 0.0473(7) 0.2868(5) 0.0193(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
S2 C10 1.601(17) . ?
S2 C13 1.614(14) . ?
C13 C12 1.355(13) . ?
C13 H13 0.9500 . ?
C12 C11 1.374(17) . ?
C12 H12 0.9500 . ?
C11 C10 1.345(18) . ?
C11 H11 0.9500 . ?
C10 C9 1.477(14) . ?
S2A C10A 1.62(2) . ?
S2A C13A 1.633(17) . ?
C13A C12A 1.352(15) . ?
C13A H13A 0.9500 . ?
C12A C11A 1.360(19) . ?
C12A H12A 0.9500 . ?
C11A C10A 1.34(2) . ?
C11A H11A 0.9500 . ?
C10A C9 1.422(17) . ?
Fe1 C15 1.789(7) . ?
Fe1 C14 1.811(6) . ?
Fe1 C16 1.822(6) . ?
Fe1 C8 2.083(5) . ?
Fe1 C7 2.104(6) . ?
Fe1 C9 2.173(6) . ?
Fe1 S1 2.3105(18) . ?
S1 C7 1.753(6) . ?
O1 C14 1.139(8) . ?
O2 C15 1.139(8) . ?
O3 C16 1.136(7) . ?
C1 C2 1.385(8) . ?
C1 C6 1.404(8) . ?
C1 H1A 0.9500 . ?
C2 C3 1.383(9) . ?
C2 H2A 0.9500 . ?
C3 C4 1.373(9) . ?
C3 H3A 0.9500 . ?
C4 C5 1.386(9) . ?
C4 H4A 0.9500 . ?
C5 C6 1.378(9) . ?
C5 H5A 0.9500 . ?
C6 C7 1.508(8) . ?
C7 C8 1.413(9) . ?
C8 C9 1.422(8) . ?
C8 H8A 0.9500 . ?
C9 H9A 0.9500 . ?
C9 H9B 0.9500 . ?

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
C10 S2 C13 94.9(8) . . ?
C12 C13 S2 110.8(11) . . ?
C12 C13 H13 124.6 . . ?
S2 C13 H13 124.6 . . ?
C13 C12 C11 110.9(12) . . ?
C13 C12 H12 124.5 . . ?
C11 C12 H12 124.5 . . ?
C10 C11 C12 112.2(13) . . ?
C10 C11 H11 123.9 . . ?
C12 C11 H11 123.9 . . ?
C11 C10 C9 131.4(15) . . ?
C11 C10 S2 110.9(9) . . ?
C9 C10 S2 117.7(12) . . ?
C10A S2A C13A 93.5(11) . . ?
C12A C13A S2A 110.2(14) . . ?
C12A C13A H13A 124.9 . . ?
S2A C13A H13A 124.9 . . ?
C13A C12A C11A 112.7(15) . . ?
C13A C12A H12A 123.7 . . ?
C11A C12A H12A 123.7 . . ?
C10A C11A C12A 111.4(16) . . ?
C10A C11A H11A 124.3 . . ?
C12A C11A H11A 124.3 . . ?
C11A C10A C9 116(2) . . ?
C11A C10A S2A 112.1(12) . . ?
C9 C10A S2A 131.4(17) . . ?
C15 Fe1 C14 92.1(3) . . ?
C15 Fe1 C16 96.2(3) . . ?
C14 Fe1 C16 103.5(3) . . ?
C15 Fe1 C8 93.0(3) . . ?
C14 Fe1 C8 128.6(3) . . ?
C16 Fe1 C8 126.6(2) . . ?
C15 Fe1 C7 118.3(2) . . ?
C14 Fe1 C7 95.1(3) . . ?
C16 Fe1 C7 140.0(3) . . ?
C8 Fe1 C7 39.4(2) . . ?
C15 Fe1 C9 96.5(3) . . ?
C14 Fe1 C9 165.0(3) . . ?
C16 Fe1 C9 87.7(2) . . ?
C8 Fe1 C9 39.0(2) . . ?
C7 Fe1 C9 70.0(2) . . ?
C15 Fe1 S1 164.7(2) . . ?
C14 Fe1 S1 87.8(2) . . ?
C16 Fe1 S1 98.71(19) . . ?
C8 Fe1 S1 75.16(18) . . ?
C7 Fe1 S1 46.50(16) . . ?
C9 Fe1 S1 80.60(18) . . ?
C7 S1 Fe1 60.5(2) . . ?
C2 C1 C6 120.1(6) . . ?
C2 C1 H1A 119.9 . . ?
C6 C1 H1A 119.9 . . ?
C3 C2 C1 120.4(6) . . ?
C3 C2 H2A 119.8 . . ?
C1 C2 H2A 119.8 . . ?
C4 C3 C2 119.3(6) . . ?
C4 C3 H3A 120.3 . . ?
C2 C3 H3A 120.3 . . ?
C3 C4 C5 120.9(6) . . ?
C3 C4 H4A 119.6 . . ?
C5 C4 H4A 119.6 . . ?
C6 C5 C4 120.6(6) . . ?
C6 C5 H5A 119.7 . . ?
C4 C5 H5A 119.7 . . ?
C5 C6 C1 118.7(6) . . ?
C5 C6 C7 120.0(5) . . ?
C1 C6 C7 121.3(5) . . ?
C8 C7 C6 123.7(5) . . ?
C8 C7 S1 115.7(4) . . ?
C6 C7 S1 120.6(4) . . ?
C8 C7 Fe1 69.5(3) . . ?
C6 C7 Fe1 128.9(4) . . ?
S1 C7 Fe1 73.0(2) . . ?
C7 C8 C9 119.9(5) . . ?
C7 C8 Fe1 71.1(3) . . ?
C9 C8 Fe1 73.9(3) . . ?
C7 C8 H8A 120.0 . . ?
C9 C8 H8A 120.0 . . ?
Fe1 C8 H8A 126.9 . . ?
C8 C9 C10A 121.9(12) . . ?
C8 C9 C10 123.1(9) . . ?
C8 C9 Fe1 67.1(3) . . ?
C10A C9 Fe1 120.8(18) . . ?
C10 C9 Fe1 123.6(13) . . ?
C8 C9 H9A 118.4 . . ?
C10 C9 H9A 118.4 . . ?
Fe1 C9 H9A 80.0 . . ?
C8 C9 H9B 119.1 . . ?
C10A C9 H9B 119.1 . . ?
Fe1 C9 H9B 82.7 . . ?
O1 C14 Fe1 178.5(6) . . ?
O2 C15 Fe1 178.4(6) . . ?
O3 C16 Fe1 177.7(6) . . ?

_refine_diff_density_max         2.215
_refine_diff_density_min         -0.639
_refine_diff_density_rms         0.212

####################################################################### 
# 
# 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_FO6584_5
_database_code_depnum_ccdc_archive 'CCDC 2169542'
loop_
_audit_author_name
_audit_author_address
'Helmar Goerls'
;University Jena
Germany
;
_audit_update_record             
;
2022-04-29 deposited with the CCDC.	2022-06-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14 Fe2 O4 S'
_chemical_formula_sum            'C20 H14 Fe2 O4 S'
_chemical_formula_weight         462.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.1138(5)
_cell_length_b                   19.2710(9)
_cell_length_c                   7.4050(5)
_cell_angle_alpha                90
_cell_angle_beta                 117.245(3)
_cell_angle_gamma                90
_cell_volume                     902.53(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    7032
_cell_measurement_theta_min      2.114
_cell_measurement_theta_max      27.470

_exptl_crystal_description       prism
_exptl_crystal_colour            red-brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_F_000             468
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.098
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.078
_exptl_absorpt_coefficient_mu    1.746
_shelx_estimated_absorpt_T_min   0.847
_shelx_estimated_absorpt_T_max   0.876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6970
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
;
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi + omega - scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7032
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.114
_diffrn_reflns_theta_max         27.470
_diffrn_reflns_theta_full        25.242
_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 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             4039
_reflns_number_gt                3951
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.899
_reflns_Friedel_fraction_max     0.953
_reflns_Friedel_fraction_full    0.973

_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       COLLECT
_computing_cell_refinement       DENZO
_computing_data_reduction        DENZO
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+0.7489P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1806 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.028(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         4039
_refine_ls_number_parameters     301
_refine_ls_number_restraints     77
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0233
_refine_ls_wR_factor_ref         0.0507
_refine_ls_wR_factor_gt          0.0499
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.049
_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 0.50646(7) 0.42589(2) 0.68034(7) 0.01438(11) Uani 1 1 d . . . . .
Fe2 Fe 0.04807(7) 0.62853(2) 0.25682(7) 0.01322(10) Uani 1 1 d . . . . .
S1 S 0.59445(14) 0.54262(4) 0.69632(14) 0.02075(18) Uani 1 1 d . . . . .
O2 O 0.3005(4) 0.29022(14) 0.5737(5) 0.0299(6) Uani 1 1 d . . . . .
O3 O 0.9355(4) 0.37923(13) 0.9639(4) 0.0304(6) Uani 1 1 d . . . . .
O4 O 0.2890(5) 0.46412(16) 0.9225(5) 0.0397(8) Uani 1 1 d . . . . .
C1 C 0.3663(5) 0.51273(17) 0.4914(5) 0.0165(7) Uani 1 1 d . . . . .
C2 C 0.3917(5) 0.45693(18) 0.3804(5) 0.0155(6) Uani 1 1 d . . . . .
C3 C 0.5949(5) 0.4285(2) 0.4368(5) 0.0174(6) Uani 1 1 d . . . . .
C4 C 0.6206(6) 0.36733(19) 0.3380(6) 0.0216(7) Uani 0.661(18) 1 d D U P A 1
C5 C 0.468(3) 0.3272(9) 0.215(3) 0.0261(18) Uani 0.661(18) 1 d D U P A 1
H5 H 0.321305 0.332036 0.174896 0.031 Uiso 0.661(18) 1 calc R U P A 1
C6 C 0.5677(18) 0.2750(7) 0.1553(19) 0.025(2) Uani 0.661(18) 1 d D U P A 1
H6 H 0.499059 0.235982 0.072902 0.030 Uiso 0.661(18) 1 calc R U P A 1
C7 C 0.7727(19) 0.2892(6) 0.2326(15) 0.022(2) Uani 0.661(18) 1 d D U P A 1
H7 H 0.873678 0.264701 0.206602 0.026 Uiso 0.661(18) 1 calc R U P A 1
O1 O 0.812(2) 0.3469(7) 0.359(2) 0.0269(11) Uani 0.661(18) 1 d D U P A 1
C4A C 0.6206(6) 0.36733(19) 0.3380(6) 0.0216(7) Uani 0.339(18) 1 d D U P A 2
C5A C 0.821(6) 0.3467(18) 0.377(6) 0.0269(11) Uani 0.339(18) 1 d D U P A 2
H5A H 0.948114 0.370532 0.461070 0.032 Uiso 0.339(18) 1 calc R U P A 2
C6A C 0.807(5) 0.2854(15) 0.272(3) 0.025(2) Uani 0.339(18) 1 d D U P A 2
H6A H 0.925315 0.259621 0.281011 0.030 Uiso 0.339(18) 1 calc R U P A 2
C7A C 0.603(4) 0.2678(14) 0.155(4) 0.022(2) Uani 0.339(18) 1 d D U P A 2
H7A H 0.548800 0.231977 0.055860 0.026 Uiso 0.339(18) 1 calc R U P A 2
O1A O 0.481(5) 0.3164(13) 0.215(5) 0.0261(18) Uani 0.339(18) 1 d D U P A 2
C8 C 0.1588(5) 0.54364(17) 0.4371(5) 0.0152(6) Uani 1 1 d . . . . .
C9 C 0.1164(6) 0.59824(18) 0.5439(5) 0.0180(7) Uani 1 1 d . . . . .
C10 C -0.1003(6) 0.61589(19) 0.4351(6) 0.0203(7) Uani 1 1 d . . . . .
C11 C -0.1953(6) 0.57250(18) 0.2603(6) 0.0198(7) Uani 1 1 d . . . . .
C12 C -0.0369(6) 0.52801(17) 0.2595(5) 0.0180(7) Uani 1 1 d . . . . .
C13 C 0.2837(6) 0.6606(2) 0.1941(7) 0.0276(8) Uani 1 1 d . . . . .
C14 C 0.1022(7) 0.6405(2) 0.0120(6) 0.0283(9) Uani 1 1 d . . . . .
C15 C -0.0678(6) 0.6833(2) -0.0082(6) 0.0246(8) Uani 1 1 d . . . . .
C16 C 0.0062(6) 0.72889(18) 0.1594(6) 0.0234(8) Uani 1 1 d . . . . .
C17 C 0.2242(6) 0.71562(19) 0.2857(6) 0.0236(8) Uani 1 1 d . . . . .
C18 C 0.3807(5) 0.34306(18) 0.6146(6) 0.0200(7) Uani 1 1 d . . . . .
C19 C 0.7668(6) 0.39523(17) 0.8574(6) 0.0203(7) Uani 1 1 d . . . . .
C20 C 0.3742(7) 0.4470(2) 0.8323(6) 0.0256(8) Uani 1 1 d . . . . .
H13 H 0.412(6) 0.644(2) 0.243(6) 0.023(11) Uiso 1 1 d . . . . .
H9 H 0.215(6) 0.622(2) 0.662(6) 0.022(10) Uiso 1 1 d . . . . .
H2 H 0.266(6) 0.436(2) 0.279(6) 0.014(9) Uiso 1 1 d . . . . .
H11 H -0.339(6) 0.5721(18) 0.150(6) 0.011(9) Uiso 1 1 d . . . . .
H16 H -0.073(7) 0.760(2) 0.185(7) 0.033(13) Uiso 1 1 d . . . . .
H12 H -0.048(6) 0.495(2) 0.165(6) 0.018(10) Uiso 1 1 d . . . . .
H3 H 0.707(6) 0.457(2) 0.491(6) 0.016(10) Uiso 1 1 d . . . . .
H17 H 0.314(7) 0.738(2) 0.412(7) 0.028(11) Uiso 1 1 d . . . . .
H14 H 0.093(9) 0.608(3) -0.069(9) 0.061(18) Uiso 1 1 d . . . . .
H10 H -0.170(7) 0.651(2) 0.474(7) 0.034(13) Uiso 1 1 d . . . . .
H15 H -0.211(8) 0.681(3) -0.113(8) 0.045(14) Uiso 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 C18 1.785(4) . ?
Fe1 C19 1.809(4) . ?
Fe1 C20 1.813(4) . ?
Fe1 C2 2.073(3) . ?
Fe1 C1 2.116(3) . ?
Fe1 C3 2.165(3) . ?
Fe1 S1 2.3235(9) . ?
Fe2 C8 2.029(3) . ?
Fe2 C13 2.030(4) . ?
Fe2 C14 2.032(4) . ?
Fe2 C12 2.032(3) . ?
Fe2 C9 2.037(3) . ?
Fe2 C16 2.038(4) . ?
Fe2 C15 2.040(4) . ?
Fe2 C17 2.046(3) . ?
Fe2 C10 2.048(3) . ?
Fe2 C11 2.050(4) . ?
S1 C1 1.736(3) . ?
O2 C18 1.139(4) . ?
O3 C19 1.136(4) . ?
O4 C20 1.137(5) . ?
C1 C2 1.414(5) . ?
C1 C8 1.467(4) . ?
C2 C3 1.418(5) . ?
C2 H2 0.96(4) . ?
C3 C4A 1.443(5) . ?
C3 C4 1.443(5) . ?
C3 H3 0.90(4) . ?
C4 C5 1.30(2) . ?
C4 O1 1.356(12) . ?
C5 C6 1.415(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.328(11) . ?
C6 H6 0.9500 . ?
C7 O1 1.399(13) . ?
C7 H7 0.9500 . ?
C4A C5A 1.38(3) . ?
C4A O1A 1.40(2) . ?
C5A C6A 1.39(3) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.35(2) . ?
C6A H6A 0.9500 . ?
C7A O1A 1.48(2) . ?
C7A H7A 0.9500 . ?
C8 C9 1.429(5) . ?
C8 C12 1.443(5) . ?
C9 C10 1.416(5) . ?
C9 H9 0.95(4) . ?
C10 C11 1.425(5) . ?
C10 H10 0.96(4) . ?
C11 C12 1.418(5) . ?
C11 H11 0.98(4) . ?
C12 H12 0.93(4) . ?
C13 C17 1.423(6) . ?
C13 C14 1.429(6) . ?
C13 H13 0.87(4) . ?
C14 C15 1.413(6) . ?
C14 H14 0.85(6) . ?
C15 C16 1.411(6) . ?
C15 H15 0.96(5) . ?
C16 C17 1.420(5) . ?
C16 H16 0.91(5) . ?
C17 H17 0.96(4) . ?

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
C18 Fe1 C19 97.15(15) . . ?
C18 Fe1 C20 91.83(17) . . ?
C19 Fe1 C20 105.86(18) . . ?
C18 Fe1 C2 93.64(15) . . ?
C19 Fe1 C2 129.87(15) . . ?
C20 Fe1 C2 122.59(16) . . ?
C18 Fe1 C1 120.09(14) . . ?
C19 Fe1 C1 138.91(15) . . ?
C20 Fe1 C1 90.68(15) . . ?
C2 Fe1 C1 39.45(13) . . ?
C18 Fe1 C3 95.42(15) . . ?
C19 Fe1 C3 91.14(15) . . ?
C20 Fe1 C3 160.55(15) . . ?
C2 Fe1 C3 39.02(13) . . ?
C1 Fe1 C3 70.08(14) . . ?
C18 Fe1 S1 165.77(11) . . ?
C19 Fe1 S1 96.71(11) . . ?
C20 Fe1 S1 87.45(12) . . ?
C2 Fe1 S1 74.93(10) . . ?
C1 Fe1 S1 45.75(9) . . ?
C3 Fe1 S1 81.10(11) . . ?
C8 Fe2 C13 106.49(15) . . ?
C8 Fe2 C14 120.26(15) . . ?
C13 Fe2 C14 41.20(17) . . ?
C8 Fe2 C12 41.63(14) . . ?
C13 Fe2 C12 124.99(15) . . ?
C14 Fe2 C12 107.21(15) . . ?
C8 Fe2 C9 41.14(13) . . ?
C13 Fe2 C9 119.90(16) . . ?
C14 Fe2 C9 155.73(16) . . ?
C12 Fe2 C9 69.30(14) . . ?
C8 Fe2 C16 161.44(15) . . ?
C13 Fe2 C16 68.40(15) . . ?
C14 Fe2 C16 68.46(16) . . ?
C12 Fe2 C16 155.81(15) . . ?
C9 Fe2 C16 124.60(15) . . ?
C8 Fe2 C15 156.07(15) . . ?
C13 Fe2 C15 68.56(16) . . ?
C14 Fe2 C15 40.61(17) . . ?
C12 Fe2 C15 120.75(15) . . ?
C9 Fe2 C15 161.86(15) . . ?
C16 Fe2 C15 40.50(16) . . ?
C8 Fe2 C17 123.91(15) . . ?
C13 Fe2 C17 40.86(16) . . ?
C14 Fe2 C17 69.08(16) . . ?
C12 Fe2 C17 162.10(15) . . ?
C9 Fe2 C17 106.49(15) . . ?
C16 Fe2 C17 40.70(15) . . ?
C15 Fe2 C17 68.58(15) . . ?
C8 Fe2 C10 68.85(14) . . ?
C13 Fe2 C10 155.11(17) . . ?
C14 Fe2 C10 162.39(17) . . ?
C12 Fe2 C10 68.70(14) . . ?
C9 Fe2 C10 40.56(14) . . ?
C16 Fe2 C10 107.84(15) . . ?
C15 Fe2 C10 125.55(16) . . ?
C17 Fe2 C10 120.12(15) . . ?
C8 Fe2 C11 69.07(14) . . ?
C13 Fe2 C11 162.49(16) . . ?
C14 Fe2 C11 125.24(17) . . ?
C12 Fe2 C11 40.63(14) . . ?
C9 Fe2 C11 68.62(15) . . ?
C16 Fe2 C11 121.12(15) . . ?
C15 Fe2 C11 108.23(15) . . ?
C17 Fe2 C11 155.60(15) . . ?
C10 Fe2 C11 40.70(15) . . ?
C1 S1 Fe1 60.79(11) . . ?
C2 C1 C8 122.0(3) . . ?
C2 C1 S1 116.3(3) . . ?
C8 C1 S1 121.7(2) . . ?
C2 C1 Fe1 68.64(19) . . ?
C8 C1 Fe1 127.8(2) . . ?
S1 C1 Fe1 73.46(12) . . ?
C1 C2 C3 120.4(3) . . ?
C1 C2 Fe1 71.91(19) . . ?
C3 C2 Fe1 74.02(19) . . ?
C1 C2 H2 117(2) . . ?
C3 C2 H2 122(2) . . ?
Fe1 C2 H2 119(2) . . ?
C2 C3 C4A 121.0(3) . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 Fe1 66.96(19) . . ?
C4A C3 Fe1 123.7(3) . . ?
C4 C3 Fe1 123.7(3) . . ?
C2 C3 H3 118(2) . . ?
C4A C3 H3 116(3) . . ?
C4 C3 H3 116(3) . . ?
Fe1 C3 H3 100(3) . . ?
C5 C4 O1 112.4(10) . . ?
C5 C4 C3 125.5(9) . . ?
O1 C4 C3 122.1(6) . . ?
C4 C5 C6 105.3(15) . . ?
C4 C5 H5 127.3 . . ?
C6 C5 H5 127.3 . . ?
C7 C6 C5 109.1(11) . . ?
C7 C6 H6 125.5 . . ?
C5 C6 H6 125.5 . . ?
C6 C7 O1 107.2(8) . . ?
C6 C7 H7 126.4 . . ?
O1 C7 H7 126.4 . . ?
C4 O1 C7 105.7(9) . . ?
C5A C4A O1A 106.9(19) . . ?
C5A C4A C3 119.3(15) . . ?
O1A C4A C3 133.5(12) . . ?
C4A C5A C6A 109(2) . . ?
C4A C5A H5A 125.4 . . ?
C6A C5A H5A 125.4 . . ?
C7A C6A C5A 110.4(18) . . ?
C7A C6A H6A 124.8 . . ?
C5A C6A H6A 124.8 . . ?
C6A C7A O1A 105(2) . . ?
C6A C7A H7A 127.6 . . ?
O1A C7A H7A 127.6 . . ?
C4A O1A C7A 108(2) . . ?
C9 C8 C12 107.3(3) . . ?
C9 C8 C1 126.0(3) . . ?
C12 C8 C1 126.5(3) . . ?
C9 C8 Fe2 69.74(19) . . ?
C12 C8 Fe2 69.30(19) . . ?
C1 C8 Fe2 123.1(2) . . ?
C10 C9 C8 108.2(3) . . ?
C10 C9 Fe2 70.1(2) . . ?
C8 C9 Fe2 69.12(19) . . ?
C10 C9 H9 124(2) . . ?
C8 C9 H9 128(2) . . ?
Fe2 C9 H9 123(2) . . ?
C9 C10 C11 108.4(3) . . ?
C9 C10 Fe2 69.33(19) . . ?
C11 C10 Fe2 69.8(2) . . ?
C9 C10 H10 125(3) . . ?
C11 C10 H10 126(3) . . ?
Fe2 C10 H10 127(3) . . ?
C12 C11 C10 108.2(3) . . ?
C12 C11 Fe2 69.00(19) . . ?
C10 C11 Fe2 69.5(2) . . ?
C12 C11 H11 121(2) . . ?
C10 C11 H11 130(2) . . ?
Fe2 C11 H11 124(2) . . ?
C11 C12 C8 107.9(3) . . ?
C11 C12 Fe2 70.4(2) . . ?
C8 C12 Fe2 69.07(19) . . ?
C11 C12 H12 129(3) . . ?
C8 C12 H12 123(3) . . ?
Fe2 C12 H12 125(2) . . ?
C17 C13 C14 108.3(3) . . ?
C17 C13 Fe2 70.2(2) . . ?
C14 C13 Fe2 69.4(2) . . ?
C17 C13 H13 124(3) . . ?
C14 C13 H13 128(3) . . ?
Fe2 C13 H13 127(3) . . ?
C15 C14 C13 107.5(4) . . ?
C15 C14 Fe2 70.0(2) . . ?
C13 C14 Fe2 69.4(2) . . ?
C15 C14 H14 125(4) . . ?
C13 C14 H14 128(4) . . ?
Fe2 C14 H14 124(4) . . ?
C16 C15 C14 108.3(3) . . ?
C16 C15 Fe2 69.7(2) . . ?
C14 C15 Fe2 69.4(2) . . ?
C16 C15 H15 125(3) . . ?
C14 C15 H15 127(3) . . ?
Fe2 C15 H15 125(3) . . ?
C15 C16 C17 108.8(3) . . ?
C15 C16 Fe2 69.8(2) . . ?
C17 C16 Fe2 70.0(2) . . ?
C15 C16 H16 126(3) . . ?
C17 C16 H16 126(3) . . ?
Fe2 C16 H16 124(3) . . ?
C16 C17 C13 107.1(3) . . ?
C16 C17 Fe2 69.3(2) . . ?
C13 C17 Fe2 69.0(2) . . ?
C16 C17 H17 127(3) . . ?
C13 C17 H17 126(3) . . ?
Fe2 C17 H17 125(3) . . ?
O2 C18 Fe1 179.6(3) . . ?
O3 C19 Fe1 175.6(3) . . ?
O4 C20 Fe1 175.8(3) . . ?

_refine_diff_density_max         0.244
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.051

