# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_jd419_sq
_database_code_depnum_ccdc_archive 'CCDC 2296883'
loop_
_audit_author_name
_audit_author_address
'Beatrice Cula'
;Humboldt Univeristy Berlin
Germany
;
_audit_update_record             
;
2023-09-22 deposited with the CCDC.	2023-12-06 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         'C13 H25 F6 Fe N3 O7 S2'
_chemical_formula_sum            'C13 H25 F6 Fe N3 O7 S2'
_chemical_formula_weight         569.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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      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                   35.662(2)
_cell_length_b                   8.8757(6)
_cell_length_c                   15.3809(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4868.5(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7055
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      25.33

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_F_000             2336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.873
_shelx_estimated_absorpt_T_min   0.824
_shelx_estimated_absorpt_T_max   0.941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6690
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23549
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_av_R_equivalents  0.0731
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.284
_diffrn_reflns_theta_max         25.392
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4478
_reflns_number_gt                3179
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0293P)²+7.0943P] 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         4478
_refine_ls_number_parameters     294
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.0901
_refine_ls_wR_factor_gt          0.0803
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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
Fe01 Fe 0.36048(2) 0.31551(5) 0.22644(3) 0.01172(12) Uani 1 1 d . . . . .
F1 F 0.46007(6) 0.4694(3) 0.33357(17) 0.0558(7) Uani 1 1 d . . . . .
O1 O 0.41678(8) 0.1701(3) 0.46935(17) 0.0516(8) Uani 1 1 d . . . . .
S1 S 0.41178(2) 0.29034(11) 0.41001(5) 0.0248(2) Uani 1 1 d . . . . .
C1 C 0.31702(9) 0.5577(4) 0.3270(2) 0.0225(8) Uani 1 1 d . . . . .
H1A H 0.309531 0.662548 0.336938 0.034 Uiso 1 1 calc R U . . .
H1B H 0.331977 0.522135 0.376330 0.034 Uiso 1 1 calc R U . . .
H1C H 0.294587 0.494792 0.321003 0.034 Uiso 1 1 calc R U . . .
N1 N 0.33972(7) 0.5482(3) 0.24607(16) 0.0151(6) Uani 1 1 d . . . . .
S2 S 0.30971(2) 0.04912(9) 0.33104(5) 0.01594(19) Uani 1 1 d . . . . .
F2 F 0.47952(6) 0.2449(3) 0.35105(15) 0.0499(7) Uani 1 1 d . . . . .
O2 O 0.39390(7) 0.4234(3) 0.44269(17) 0.0451(8) Uani 1 1 d . . . . .
C2 C 0.27966(9) 0.2934(4) 0.1407(2) 0.0231(8) Uani 1 1 d . . . . .
H2A H 0.263718 0.310368 0.089690 0.035 Uiso 1 1 calc R U . . .
H2B H 0.271163 0.357675 0.188596 0.035 Uiso 1 1 calc R U . . .
H2C H 0.278046 0.187472 0.158192 0.035 Uiso 1 1 calc R U . . .
N2 N 0.31907(7) 0.3309(3) 0.11874(16) 0.0158(6) Uani 1 1 d . . . . .
C3 C 0.38944(10) 0.0231(4) 0.1487(2) 0.0260(9) Uani 1 1 d . . . . .
H3A H 0.363329 -0.011005 0.146422 0.039 Uiso 1 1 calc R U . . .
H3B H 0.399493 0.006108 0.207228 0.039 Uiso 1 1 calc R U . . .
H3C H 0.404363 -0.033426 0.106343 0.039 Uiso 1 1 calc R U . . .
N3 N 0.39117(7) 0.1853(3) 0.12803(16) 0.0165(6) Uani 1 1 d . . . . .
O3 O 0.39927(6) 0.2457(3) 0.32381(13) 0.0199(5) Uani 1 1 d . . . . .
F3 F 0.47717(6) 0.3932(3) 0.45961(14) 0.0534(7) Uani 1 1 d . . . . .
F4 F 0.30877(6) 0.1701(2) 0.48595(12) 0.0336(5) Uani 1 1 d . . . . .
O4 O 0.32254(6) 0.1939(2) 0.29718(14) 0.0195(5) Uani 1 1 d . . . . .
C4 C 0.31631(10) 0.5929(4) 0.1698(2) 0.0228(8) Uani 1 1 d . . . . .
H4A H 0.322702 0.697304 0.152753 0.027 Uiso 1 1 calc R U . . .
H4AB H 0.289536 0.591060 0.186747 0.027 Uiso 1 1 calc R U . . .
O5 O 0.33883(6) -0.0470(3) 0.36273(14) 0.0246(6) Uani 1 1 d . . . . .
F5 F 0.26733(5) -0.0023(2) 0.46635(12) 0.0298(5) Uani 1 1 d . . . . .
C5 C 0.32210(10) 0.4892(4) 0.0923(2) 0.0217(8) Uani 1 1 d . . . . .
H5A H 0.303032 0.511501 0.047337 0.026 Uiso 1 1 calc R U . . .
H5AB H 0.347171 0.507603 0.066801 0.026 Uiso 1 1 calc R U . . .
F6 F 0.25972(5) 0.2161(2) 0.40973(13) 0.0329(5) Uani 1 1 d . . . . .
O6 O 0.28125(7) -0.0196(3) 0.27852(15) 0.0289(6) Uani 1 1 d . . . . .
C6 C 0.33164(9) 0.2258(4) 0.0497(2) 0.0226(8) Uani 1 1 d . . . . .
H6A H 0.320979 0.258769 -0.006627 0.027 Uiso 1 1 calc R U . . .
H6AB H 0.321719 0.124002 0.062387 0.027 Uiso 1 1 calc R U . . .
C7 C 0.37365(10) 0.2171(4) 0.0416(2) 0.0245(8) Uani 1 1 d . . . . .
H7A H 0.380446 0.136369 0.000091 0.029 Uiso 1 1 calc R U . . .
H7AB H 0.383386 0.313675 0.018611 0.029 Uiso 1 1 calc R U . . .
O008 O 0.40530(6) 0.4603(2) 0.18098(14) 0.0197(5) Uani 1 1 d . . . . .
C8 C 0.43087(9) 0.2341(4) 0.1288(2) 0.0230(8) Uani 1 1 d . . . . .
H8A H 0.444087 0.189419 0.078366 0.028 Uiso 1 1 calc R U . . .
H8AB H 0.443144 0.197107 0.182410 0.028 Uiso 1 1 calc R U . . .
C9 C 0.43392(9) 0.4043(4) 0.1247(2) 0.0218(8) Uani 1 1 d . . . . .
H9A H 0.458955 0.437861 0.144720 0.026 Uiso 1 1 calc R U . . .
H9AB H 0.429971 0.440546 0.064541 0.026 Uiso 1 1 calc R U . . .
C10 C 0.40146(10) 0.6199(4) 0.1864(2) 0.0231(8) Uani 1 1 d . . . . .
H10A H 0.392602 0.661705 0.130340 0.028 Uiso 1 1 calc R U . . .
H10B H 0.425737 0.667372 0.201327 0.028 Uiso 1 1 calc R U . . .
C11 C 0.37310(9) 0.6470(4) 0.2568(2) 0.0223(8) Uani 1 1 d . . . . .
H11A H 0.384754 0.627480 0.314138 0.027 Uiso 1 1 calc R U . . .
H11B H 0.365093 0.753804 0.255375 0.027 Uiso 1 1 calc R U . . .
C12 C 0.45954(10) 0.3531(5) 0.3883(2) 0.0315(10) Uani 1 1 d . . . . .
C13 C 0.28509(9) 0.1120(4) 0.4281(2) 0.0204(8) 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
Fe01 O4 2.045(2) . ?
Fe01 O3 2.131(2) . ?
Fe01 O008 2.167(2) . ?
Fe01 N3 2.196(3) . ?
Fe01 N1 2.214(3) . ?
Fe01 N2 2.223(3) . ?
F1 C12 1.331(4) . ?
O1 S1 1.415(3) . ?
S1 O2 1.434(3) . ?
S1 O3 1.454(2) . ?
S1 C12 1.823(4) . ?
C1 N1 1.487(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
N1 C11 1.488(4) . ?
N1 C4 1.494(4) . ?
S2 O5 1.430(2) . ?
S2 O6 1.433(2) . ?
S2 O4 1.460(2) . ?
S2 C13 1.819(3) . ?
F2 C12 1.326(4) . ?
C2 N2 1.483(4) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
N2 C5 1.467(4) . ?
N2 C6 1.483(4) . ?
C3 N3 1.476(4) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
N3 C8 1.480(4) . ?
N3 C7 1.496(4) . ?
F3 C12 1.314(4) . ?
F4 C13 1.331(4) . ?
C4 C5 1.519(5) . ?
C4 H4A 0.9900 . ?
C4 H4AB 0.9900 . ?
F5 C13 1.333(4) . ?
C5 H5A 0.9900 . ?
C5 H5AB 0.9900 . ?
F6 C13 1.323(4) . ?
C6 C7 1.505(5) . ?
C6 H6A 0.9900 . ?
C6 H6AB 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
O008 C10 1.425(4) . ?
O008 C9 1.428(4) . ?
C8 C9 1.516(5) . ?
C8 H8A 0.9900 . ?
C8 H8AB 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9AB 0.9900 . ?
C10 C11 1.502(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Fe01 O3 84.37(8) . . ?
O4 Fe01 O008 166.67(9) . . ?
O3 Fe01 O008 85.44(8) . . ?
O4 Fe01 N3 114.75(10) . . ?
O3 Fe01 N3 90.45(9) . . ?
O008 Fe01 N3 73.87(9) . . ?
O4 Fe01 N1 101.46(9) . . ?
O3 Fe01 N1 113.11(9) . . ?
O008 Fe01 N1 74.78(9) . . ?
N3 Fe01 N1 138.69(10) . . ?
O4 Fe01 N2 89.39(9) . . ?
O3 Fe01 N2 166.58(9) . . ?
O008 Fe01 N2 102.30(9) . . ?
N3 Fe01 N2 81.37(9) . . ?
N1 Fe01 N2 79.76(9) . . ?
O1 S1 O2 116.82(18) . . ?
O1 S1 O3 114.90(16) . . ?
O2 S1 O3 114.07(15) . . ?
O1 S1 C12 103.36(18) . . ?
O2 S1 C12 103.19(18) . . ?
O3 S1 C12 101.71(15) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1 N1 C11 108.0(2) . . ?
C1 N1 C4 109.7(2) . . ?
C11 N1 C4 112.2(3) . . ?
C1 N1 Fe01 110.45(19) . . ?
C11 N1 Fe01 107.33(19) . . ?
C4 N1 Fe01 109.12(18) . . ?
O5 S2 O6 116.93(15) . . ?
O5 S2 O4 114.76(13) . . ?
O6 S2 O4 113.30(14) . . ?
O5 S2 C13 104.71(15) . . ?
O6 S2 C13 104.54(15) . . ?
O4 S2 C13 100.01(14) . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C5 N2 C6 112.4(3) . . ?
C5 N2 C2 110.4(3) . . ?
C6 N2 C2 108.0(2) . . ?
C5 N2 Fe01 102.49(19) . . ?
C6 N2 Fe01 107.10(19) . . ?
C2 N2 Fe01 116.51(19) . . ?
N3 C3 H3A 109.5 . . ?
N3 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N3 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C3 N3 C8 108.9(3) . . ?
C3 N3 C7 111.0(3) . . ?
C8 N3 C7 110.6(3) . . ?
C3 N3 Fe01 110.10(19) . . ?
C8 N3 Fe01 108.51(19) . . ?
C7 N3 Fe01 107.76(19) . . ?
S1 O3 Fe01 139.53(14) . . ?
S2 O4 Fe01 149.55(15) . . ?
N1 C4 C5 112.3(3) . . ?
N1 C4 H4A 109.1 . . ?
C5 C4 H4A 109.1 . . ?
N1 C4 H4AB 109.1 . . ?
C5 C4 H4AB 109.1 . . ?
H4A C4 H4AB 107.9 . . ?
N2 C5 C4 110.6(3) . . ?
N2 C5 H5A 109.5 . . ?
C4 C5 H5A 109.5 . . ?
N2 C5 H5AB 109.5 . . ?
C4 C5 H5AB 109.5 . . ?
H5A C5 H5AB 108.1 . . ?
N2 C6 C7 113.1(3) . . ?
N2 C6 H6A 109.0 . . ?
C7 C6 H6A 109.0 . . ?
N2 C6 H6AB 109.0 . . ?
C7 C6 H6AB 109.0 . . ?
H6A C6 H6AB 107.8 . . ?
N3 C7 C6 110.6(3) . . ?
N3 C7 H7A 109.5 . . ?
C6 C7 H7A 109.5 . . ?
N3 C7 H7AB 109.5 . . ?
C6 C7 H7AB 109.5 . . ?
H7A C7 H7AB 108.1 . . ?
C10 O008 C9 116.7(2) . . ?
C10 O008 Fe01 119.99(18) . . ?
C9 O008 Fe01 121.10(19) . . ?
N3 C8 C9 111.1(3) . . ?
N3 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
N3 C8 H8AB 109.4 . . ?
C9 C8 H8AB 109.4 . . ?
H8A C8 H8AB 108.0 . . ?
O008 C9 C8 105.7(3) . . ?
O008 C9 H9A 110.6 . . ?
C8 C9 H9A 110.6 . . ?
O008 C9 H9AB 110.6 . . ?
C8 C9 H9AB 110.6 . . ?
H9A C9 H9AB 108.7 . . ?
O008 C10 C11 105.4(3) . . ?
O008 C10 H10A 110.7 . . ?
C11 C10 H10A 110.7 . . ?
O008 C10 H10B 110.7 . . ?
C11 C10 H10B 110.7 . . ?
H10A C10 H10B 108.8 . . ?
N1 C11 C10 111.3(3) . . ?
N1 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
N1 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
F3 C12 F2 107.4(3) . . ?
F3 C12 F1 108.1(3) . . ?
F2 C12 F1 106.3(3) . . ?
F3 C12 S1 112.1(3) . . ?
F2 C12 S1 111.1(3) . . ?
F1 C12 S1 111.5(3) . . ?
F6 C13 F4 107.8(3) . . ?
F6 C13 F5 107.5(3) . . ?
F4 C13 F5 107.5(3) . . ?
F6 C13 S2 111.7(2) . . ?
F4 C13 S2 111.2(2) . . ?
F5 C13 S2 111.0(2) . . ?

_refine_diff_density_max         0.353
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.080




_chemical_properties_physical    Air-sensitive,Oxygen-sensitive
