# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_WE12751
_database_code_depnum_ccdc_archive 'CCDC 2189751'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;ISCR
France
;
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2022-09-25 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 22 janvier 2021                                          #
#------------------------------------------------------------------------------#


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H13 F Fe O2 S2'
_chemical_formula_sum            'C16 H13 F Fe O2 S2'
_chemical_formula_weight         376.23
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#


_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
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                   9.4238(7)
_cell_length_b                   14.4798(10)
_cell_length_c                   11.2622(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.638(3)
_cell_angle_gamma                90
_cell_volume                     1515.09(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4557
_cell_measurement_theta_min      2.6047
_cell_measurement_theta_max      27.4628
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      0.0613512
_diffrn_orient_matrix_UB_21      0.0840123
_diffrn_orient_matrix_UB_31      0.0276192
_diffrn_orient_matrix_UB_12      0.0534816
_diffrn_orient_matrix_UB_22      -0.0280385
_diffrn_orient_matrix_UB_32      -0.0335122
_diffrn_orient_matrix_UB_13      -0.0157857
_diffrn_orient_matrix_UB_23      0.0539736
_diffrn_orient_matrix_UB_33      -0.0703501


#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.440
_exptl_crystal_size_min          0.250
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             768
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.284
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.647
_exptl_absorpt_correction_T_max  0.725

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

# Software                   : BIS 2014.5.0.0/23-May-2014 && APEX2_2014.11-0   #
# Number of scans            :        3                                        #
# Total number of frames     :      294                                        #
# Total length of scans      :   294.00 (deg.)                                 #
# Rotation speed             :     5.00 sec./deg.                              #
# Total exposition time      :         24.5 min.                               #
#                                                                              #
#    Scan  Time(s)  Width  DX (mm)  Frames  Theta  Omega    Phi    Chi   T(K)  #
#..............................................................................#
#                                                                              #
#  1 Omega     5.0   1.00     35.0      93 343.95 342.93 151.13 332.39 296.15  #
#  2 Omega     5.0   1.00     35.0     105  16.05  14.69  27.38 308.40 296.15  #
#  3 Omega     5.0   1.00     35.0      96 343.95 250.74   0.95  31.11 296.15  #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'APEXII Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.33
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_uneti/neti     0.0356
_diffrn_reflns_av_r_equivalents  0.0320
_diffrn_reflns_number            10849
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.311
_diffrn_reflns_theta_max         27.562
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_reflns_number_total             3482
_reflns_number_gt                3013
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2020)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0282P)²+0.6644P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         3482
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0285
_refine_ls_wR_factor_ref         0.0696
_refine_ls_wR_factor_gt          0.0664
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.065

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'
F F 0.0171 0.0103 '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'
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'

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 0.07804(3) 0.68212(2) 0.66755(2) 0.01372(8) Uani 1 1 d . . . . .
S1 S 0.39168(5) 0.76432(3) 0.63860(4) 0.01930(11) Uani 1 1 d . . . . .
S2 S 0.32773(5) 0.52104(3) 0.64275(4) 0.02013(11) Uani 1 1 d . . . . .
C1 C -0.0134(2) 0.63639(13) 0.49998(17) 0.0246(4) Uani 1 1 d . . . . .
H1 H 0.021669 0.587859 0.456052 0.030 Uiso 1 1 calc R U . . .
C2 C 0.0237(2) 0.73112(13) 0.49574(17) 0.0243(4) Uani 1 1 d . . . . .
H2 H 0.087808 0.757230 0.448237 0.029 Uiso 1 1 calc R U . . .
C3 C -0.0515(2) 0.77999(13) 0.57467(18) 0.0258(5) Uani 1 1 d . . . . .
H3 H -0.046712 0.844596 0.589469 0.031 Uiso 1 1 calc R U . . .
C4 C -0.1349(2) 0.71592(15) 0.62745(19) 0.0293(5) Uani 1 1 d . . . . .
H4 H -0.195957 0.729804 0.684153 0.035 Uiso 1 1 calc R U . . .
C5 C -0.1116(2) 0.62701(14) 0.58106(19) 0.0280(5) Uani 1 1 d . . . . .
H5 H -0.154648 0.571046 0.601085 0.034 Uiso 1 1 calc R U . . .
C6 C 0.28584(19) 0.70618(11) 0.72370(15) 0.0140(3) Uani 1 1 d . . . . .
C7 C 0.2052(2) 0.75084(13) 0.80392(16) 0.0186(4) Uani 1 1 d . . . . .
H7 H 0.204211 0.815103 0.820737 0.022 Uiso 1 1 calc R U . . .
C8 C 0.1271(2) 0.68161(13) 0.85357(17) 0.0220(4) Uani 1 1 d . . . . .
H8 H 0.063607 0.691638 0.909539 0.026 Uiso 1 1 calc R U . . .
C9 C 0.1590(2) 0.59450(13) 0.80609(16) 0.0199(4) Uani 1 1 d . . . . .
H9 H 0.120971 0.536785 0.825733 0.024 Uiso 1 1 calc R U . . .
C10 C 0.25717(19) 0.60773(11) 0.72446(15) 0.0150(4) Uani 1 1 d . . . . .
F11 F 0.54495(13) 0.74067(9) 0.70910(12) 0.0365(3) Uani 1 1 d . . . . .
O12 O 0.38898(17) 0.72631(10) 0.52324(13) 0.0345(4) Uani 1 1 d . . . . .
O13 O 0.37695(17) 0.86059(9) 0.65315(14) 0.0333(4) Uani 1 1 d . . . . .
C14 C 0.5008(2) 0.50262(11) 0.72908(16) 0.0184(4) Uani 1 1 d . . . . .
C15 C 0.5943(2) 0.44717(13) 0.67657(19) 0.0289(5) Uani 1 1 d . . . . .
H15 H 0.564021 0.421430 0.598873 0.035 Uiso 1 1 calc R U . . .
C16 C 0.7311(3) 0.42989(16) 0.7381(2) 0.0410(6) Uani 1 1 d . . . . .
H16 H 0.794204 0.391133 0.703072 0.049 Uiso 1 1 calc R U . . .
C17 C 0.7771(2) 0.46832(15) 0.8500(2) 0.0403(6) Uani 1 1 d . . . . .
H17 H 0.872215 0.457342 0.890905 0.048 Uiso 1 1 calc R U . . .
C18 C 0.6840(2) 0.52304(14) 0.9023(2) 0.0344(5) Uani 1 1 d . . . . .
H18 H 0.714958 0.549246 0.979639 0.041 Uiso 1 1 calc R U . . .
C19 C 0.5462(2) 0.53954(12) 0.84227(18) 0.0241(4) Uani 1 1 d . . . . .
H19 H 0.482254 0.576455 0.878933 0.029 Uiso 1 1 calc R U . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_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 C6 1.9853(18) . ?
Fe1 C10 2.0146(17) . ?
Fe1 C4 2.041(2) . ?
Fe1 C3 2.0410(18) . ?
Fe1 C7 2.0416(18) . ?
Fe1 C2 2.0440(19) . ?
Fe1 C1 2.0488(19) . ?
Fe1 C5 2.0488(19) . ?
Fe1 C9 2.0563(18) . ?
Fe1 C8 2.0685(18) . ?
S1 O12 1.4072(15) . ?
S1 O13 1.4131(14) . ?
S1 F11 1.5652(13) . ?
S1 C6 1.7152(18) . ?
S2 C10 1.7520(17) . ?
S2 C14 1.7733(19) . ?
C1 C5 1.412(3) . ?
C1 C2 1.418(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.416(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.410(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.420(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.429(2) . ?
C6 C10 1.451(2) . ?
C7 C8 1.413(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.422(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.422(3) . ?
C9 H9 0.9500 . ?
C14 C19 1.383(3) . ?
C14 C15 1.395(3) . ?
C15 C16 1.381(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.379(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.385(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.381(3) . ?
C18 H18 0.9500 . ?
C19 H19 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
C6 Fe1 C10 42.54(7) . . ?
C6 Fe1 C4 155.38(8) . . ?
C10 Fe1 C4 159.87(8) . . ?
C6 Fe1 C3 121.00(8) . . ?
C10 Fe1 C3 158.73(8) . . ?
C4 Fe1 C3 40.40(9) . . ?
C6 Fe1 C7 41.54(7) . . ?
C10 Fe1 C7 70.51(7) . . ?
C4 Fe1 C7 118.74(8) . . ?
C3 Fe1 C7 105.82(8) . . ?
C6 Fe1 C2 108.55(8) . . ?
C10 Fe1 C2 123.41(8) . . ?
C4 Fe1 C2 68.04(9) . . ?
C3 Fe1 C2 40.56(8) . . ?
C7 Fe1 C2 124.43(8) . . ?
C6 Fe1 C1 126.18(8) . . ?
C10 Fe1 C1 108.72(7) . . ?
C4 Fe1 C1 68.13(8) . . ?
C3 Fe1 C1 68.23(8) . . ?
C7 Fe1 C1 162.51(8) . . ?
C2 Fe1 C1 40.55(8) . . ?
C6 Fe1 C5 162.81(8) . . ?
C10 Fe1 C5 124.12(8) . . ?
C4 Fe1 C5 40.63(8) . . ?
C3 Fe1 C5 68.11(8) . . ?
C7 Fe1 C5 154.54(9) . . ?
C2 Fe1 C5 67.96(8) . . ?
C1 Fe1 C5 40.30(9) . . ?
C6 Fe1 C9 69.24(7) . . ?
C10 Fe1 C9 40.87(7) . . ?
C4 Fe1 C9 122.83(8) . . ?
C3 Fe1 C9 158.67(8) . . ?
C7 Fe1 C9 68.49(7) . . ?
C2 Fe1 C9 159.21(8) . . ?
C1 Fe1 C9 123.02(8) . . ?
C5 Fe1 C9 107.69(8) . . ?
C6 Fe1 C8 68.70(7) . . ?
C10 Fe1 C8 69.06(7) . . ?
C4 Fe1 C8 105.64(8) . . ?
C3 Fe1 C8 122.32(8) . . ?
C7 Fe1 C8 40.21(8) . . ?
C2 Fe1 C8 159.74(8) . . ?
C1 Fe1 C8 156.92(8) . . ?
C5 Fe1 C8 120.62(8) . . ?
C9 Fe1 C8 40.33(7) . . ?
O12 S1 O13 120.39(9) . . ?
O12 S1 F11 104.79(9) . . ?
O13 S1 F11 104.90(8) . . ?
O12 S1 C6 113.68(9) . . ?
O13 S1 C6 109.99(9) . . ?
F11 S1 C6 100.53(8) . . ?
C10 S2 C14 102.40(8) . . ?
C5 C1 C2 107.87(18) . . ?
C5 C1 Fe1 69.85(11) . . ?
C2 C1 Fe1 69.54(10) . . ?
C5 C1 H1 126.1 . . ?
C2 C1 H1 126.1 . . ?
Fe1 C1 H1 126.1 . . ?
C3 C2 C1 108.06(18) . . ?
C3 C2 Fe1 69.61(11) . . ?
C1 C2 Fe1 69.91(11) . . ?
C3 C2 H2 126.0 . . ?
C1 C2 H2 126.0 . . ?
Fe1 C2 H2 126.1 . . ?
C4 C3 C2 107.99(18) . . ?
C4 C3 Fe1 69.81(11) . . ?
C2 C3 Fe1 69.83(11) . . ?
C4 C3 H3 126.0 . . ?
C2 C3 H3 126.0 . . ?
Fe1 C3 H3 125.9 . . ?
C3 C4 C5 108.08(19) . . ?
C3 C4 Fe1 69.79(11) . . ?
C5 C4 Fe1 69.97(11) . . ?
C3 C4 H4 126.0 . . ?
C5 C4 H4 126.0 . . ?
Fe1 C4 H4 125.9 . . ?
C1 C5 C4 108.00(18) . . ?
C1 C5 Fe1 69.85(11) . . ?
C4 C5 Fe1 69.40(11) . . ?
C1 C5 H5 126.0 . . ?
C4 C5 H5 126.0 . . ?
Fe1 C5 H5 126.3 . . ?
C7 C6 C10 108.75(15) . . ?
C7 C6 S1 123.49(13) . . ?
C10 C6 S1 127.71(13) . . ?
C7 C6 Fe1 71.34(10) . . ?
C10 C6 Fe1 69.81(10) . . ?
S1 C6 Fe1 122.88(9) . . ?
C8 C7 C6 107.25(15) . . ?
C8 C7 Fe1 70.92(11) . . ?
C6 C7 Fe1 67.12(10) . . ?
C8 C7 H7 126.4 . . ?
C6 C7 H7 126.4 . . ?
Fe1 C7 H7 127.1 . . ?
C7 C8 C9 108.87(16) . . ?
C7 C8 Fe1 68.87(10) . . ?
C9 C8 Fe1 69.37(10) . . ?
C7 C8 H8 125.6 . . ?
C9 C8 H8 125.6 . . ?
Fe1 C8 H8 127.8 . . ?
C8 C9 C10 108.98(16) . . ?
C8 C9 Fe1 70.30(10) . . ?
C10 C9 Fe1 67.99(10) . . ?
C8 C9 H9 125.5 . . ?
C10 C9 H9 125.5 . . ?
Fe1 C9 H9 127.8 . . ?
C9 C10 C6 106.14(15) . . ?
C9 C10 S2 126.03(13) . . ?
C6 C10 S2 127.83(14) . . ?
C9 C10 Fe1 71.14(10) . . ?
C6 C10 Fe1 67.65(9) . . ?
S2 C10 Fe1 125.98(9) . . ?
C19 C14 C15 119.56(18) . . ?
C19 C14 S2 124.18(15) . . ?
C15 C14 S2 116.26(15) . . ?
C16 C15 C14 119.7(2) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C17 C16 C15 120.6(2) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 119.7(2) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C19 C18 C17 120.1(2) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C14 120.4(2) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?

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
C5 C1 C2 C3 0.2(2) . . . . ?
Fe1 C1 C2 C3 -59.37(13) . . . . ?
C5 C1 C2 Fe1 59.56(13) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
Fe1 C2 C3 C4 -59.61(13) . . . . ?
C1 C2 C3 Fe1 59.56(13) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
Fe1 C3 C4 C5 -59.73(13) . . . . ?
C2 C3 C4 Fe1 59.63(13) . . . . ?
C2 C1 C5 C4 -0.3(2) . . . . ?
Fe1 C1 C5 C4 59.11(13) . . . . ?
C2 C1 C5 Fe1 -59.37(13) . . . . ?
C3 C4 C5 C1 0.2(2) . . . . ?
Fe1 C4 C5 C1 -59.40(14) . . . . ?
C3 C4 C5 Fe1 59.62(14) . . . . ?
O12 S1 C6 C7 -142.97(15) . . . . ?
O13 S1 C6 C7 -4.61(18) . . . . ?
F11 S1 C6 C7 105.63(15) . . . . ?
O12 S1 C6 C10 34.23(19) . . . . ?
O13 S1 C6 C10 172.59(15) . . . . ?
F11 S1 C6 C10 -77.17(17) . . . . ?
O12 S1 C6 Fe1 -54.64(14) . . . . ?
O13 S1 C6 Fe1 83.72(12) . . . . ?
F11 S1 C6 Fe1 -166.04(10) . . . . ?
C10 C6 C7 C8 -0.2(2) . . . . ?
S1 C6 C7 C8 177.45(13) . . . . ?
Fe1 C6 C7 C8 59.83(13) . . . . ?
C10 C6 C7 Fe1 -60.04(12) . . . . ?
S1 C6 C7 Fe1 117.62(13) . . . . ?
C6 C7 C8 C9 0.5(2) . . . . ?
Fe1 C7 C8 C9 57.91(13) . . . . ?
C6 C7 C8 Fe1 -57.44(12) . . . . ?
C7 C8 C9 C10 -0.6(2) . . . . ?
Fe1 C8 C9 C10 57.04(13) . . . . ?
C7 C8 C9 Fe1 -57.61(13) . . . . ?
C8 C9 C10 C6 0.4(2) . . . . ?
Fe1 C9 C10 C6 58.86(11) . . . . ?
C8 C9 C10 S2 -179.71(13) . . . . ?
Fe1 C9 C10 S2 -121.28(15) . . . . ?
C8 C9 C10 Fe1 -58.43(13) . . . . ?
C7 C6 C10 C9 -0.14(19) . . . . ?
S1 C6 C10 C9 -177.67(14) . . . . ?
Fe1 C6 C10 C9 -61.13(12) . . . . ?
C7 C6 C10 S2 180.00(13) . . . . ?
S1 C6 C10 S2 2.5(2) . . . . ?
Fe1 C6 C10 S2 119.01(14) . . . . ?
C7 C6 C10 Fe1 60.99(12) . . . . ?
S1 C6 C10 Fe1 -116.54(15) . . . . ?
C14 S2 C10 C9 -99.97(17) . . . . ?
C14 S2 C10 C6 79.86(17) . . . . ?
C14 S2 C10 Fe1 168.08(11) . . . . ?
C10 S2 C14 C19 9.95(18) . . . . ?
C10 S2 C14 C15 -169.92(14) . . . . ?
C19 C14 C15 C16 -0.1(3) . . . . ?
S2 C14 C15 C16 179.80(16) . . . . ?
C14 C15 C16 C17 -1.2(3) . . . . ?
C15 C16 C17 C18 1.5(3) . . . . ?
C16 C17 C18 C19 -0.5(3) . . . . ?
C17 C18 C19 C14 -0.8(3) . . . . ?
C15 C14 C19 C18 1.1(3) . . . . ?
S2 C14 C19 C18 -178.77(15) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


####################################################################### 
# 
# 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_WE12771
_database_code_depnum_ccdc_archive 'CCDC 2189752'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;ISCR
France
;
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2022-09-25 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 22 janvier 2021                                          #
#------------------------------------------------------------------------------#


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H12 F Fe N O2 S'
_chemical_formula_sum            'C15 H12 F Fe N O2 S'
_chemical_formula_weight         345.17
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration rm/ad/rmad/syn/unk/.

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#


_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.8514(7)
_cell_length_b                   9.7058(8)
_cell_length_c                   20.4257(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1358.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2475
_cell_measurement_theta_min      2.8953
_cell_measurement_theta_max      26.7453
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      0.0083346
_diffrn_orient_matrix_UB_21      0.1302549
_diffrn_orient_matrix_UB_31      -0.0653249
_diffrn_orient_matrix_UB_12      -0.0604417
_diffrn_orient_matrix_UB_22      0.0404639
_diffrn_orient_matrix_UB_32      0.0729716
_diffrn_orient_matrix_UB_13      0.0395499
_diffrn_orient_matrix_UB_23      0.0108743
_diffrn_orient_matrix_UB_33      0.0267289


#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.170
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             704
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.278
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.707
_exptl_absorpt_correction_T_max  0.805

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

# Software                   : BIS 2014.5.0.0/23-May-2014 && APEX2_2014.11-0   #
# Number of scans            :        2                                        #
# Total number of frames     :      193                                        #
# Total length of scans      :   193.00 (deg.)                                 #
# Rotation speed             :     8.00 sec./deg.                              #
# Total exposition time      :         25.7 min.                               #
#                                                                              #
#    Scan  Time(s)  Width  DX (mm)  Frames  Theta  Omega    Phi    Chi   T(K)  #
#..............................................................................#
#                                                                              #
#  1 Omega     8.0   1.00     35.0      93 343.95 348.46  10.26 320.72 296.15  #
#  2 Omega     8.0   1.00     35.0     100  16.05  14.04 240.68 319.21 296.15  #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'APEXII Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.33
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_uneti/neti     0.0604
_diffrn_reflns_av_r_equivalents  0.0439
_diffrn_reflns_number            6538
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.994
_diffrn_reflns_theta_max         27.536
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.989
_reflns_number_total             3108
_reflns_number_gt                2820
_reflns_threshold_expression     >2sigma(I)
_reflns_Friedel_coverage         0.721
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    0.998

_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.
;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2020)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0280P)²+0.3800P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         3108
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1199
_refine_ls_wR_factor_gt          0.1159
_refine_ls_goodness_of_fit_ref   1.491
_refine_ls_restrained_S_all      1.491
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         1.146
_refine_diff_density_min         -0.858
_refine_diff_density_rms         0.106
_refine_ls_abs_structure_details 
;
Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.50(4)

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.44611(10) 0.49800(8) 0.60466(4) 0.0174(2) Uani 1 1 d . . . . .
C1 C 0.4724(12) 0.4415(9) 0.5098(4) 0.0491(10) Uani 1 1 d . . . . .
H1 H 0.424946 0.492705 0.473520 0.059 Uiso 1 1 calc R U . . .
C2 C 0.6576(13) 0.4557(8) 0.5368(4) 0.0491(10) Uani 1 1 d . . . . .
H2 H 0.757280 0.517427 0.523097 0.059 Uiso 1 1 calc R U . . .
C3 C 0.6673(13) 0.3616(8) 0.5876(4) 0.0491(10) Uani 1 1 d . . . . .
H3 H 0.777416 0.347393 0.615032 0.059 Uiso 1 1 calc R U . . .
C4 C 0.4922(12) 0.2915(9) 0.5923(4) 0.0491(10) Uani 1 1 d . . . . .
H4 H 0.461069 0.221378 0.623011 0.059 Uiso 1 1 calc R U . . .
C5 C 0.3681(13) 0.3440(8) 0.5428(4) 0.0491(10) Uani 1 1 d . . . . .
H5 H 0.237465 0.316504 0.534227 0.059 Uiso 1 1 calc R U . . .
C6 C 0.2800(8) 0.6713(5) 0.6086(3) 0.0163(11) Uani 1 1 d . . . . .
H6 H 0.221725 0.716279 0.572204 0.020 Uiso 1 1 calc R U . . .
C7 C 0.1946(9) 0.5698(6) 0.6479(3) 0.0208(13) Uani 1 1 d . . . . .
H7 H 0.065778 0.535184 0.642761 0.025 Uiso 1 1 calc R U . . .
C8 C 0.3287(8) 0.5264(6) 0.6963(3) 0.0186(12) Uani 1 1 d . . . . .
H8 H 0.305390 0.457593 0.728456 0.022 Uiso 1 1 calc R U . . .
C9 C 0.5041(8) 0.6030(5) 0.6888(3) 0.0154(11) Uani 1 1 d . . . . .
C10 C 0.4722(8) 0.6944(5) 0.6339(3) 0.0142(11) Uani 1 1 d . . . . .
S1 S 0.6322(2) 0.80435(14) 0.59556(7) 0.0188(3) Uani 1 1 d . . . . .
O11 O 0.8295(6) 0.7614(4) 0.5995(2) 0.0266(10) Uani 1 1 d . . . . .
O12 O 0.5528(6) 0.8438(4) 0.5339(2) 0.0292(11) Uani 1 1 d . . . . .
F13 F 0.6154(5) 0.9360(3) 0.63887(17) 0.0286(8) Uani 1 1 d . . . . .
C14 C 0.6736(8) 0.5965(5) 0.7331(3) 0.0133(11) Uani 1 1 d . . . . .
C15 C 0.7266(9) 0.4709(5) 0.7624(3) 0.0195(12) Uani 1 1 d . . . . .
H15 H 0.659412 0.388048 0.752050 0.023 Uiso 1 1 calc R U . . .
C16 C 0.8776(9) 0.4711(6) 0.8064(3) 0.0217(13) Uani 1 1 d . . . . .
H16 H 0.916885 0.387882 0.827106 0.026 Uiso 1 1 calc R U . . .
C17 C 0.9722(9) 0.5932(7) 0.8204(3) 0.0237(13) Uani 1 1 d . . . . .
H17 H 1.076997 0.595620 0.850879 0.028 Uiso 1 1 calc R U . . .
C18 C 0.9115(9) 0.7105(6) 0.7894(3) 0.0244(13) Uani 1 1 d . . . . .
H18 H 0.976847 0.794328 0.799276 0.029 Uiso 1 1 calc R U . . .
N19 N 0.7645(7) 0.7140(5) 0.7458(2) 0.0200(10) Uani 1 1 d . . . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_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 C10 2.006(5) . ?
Fe1 C1 2.021(8) . ?
Fe1 C5 2.029(8) . ?
Fe1 C6 2.033(5) . ?
Fe1 C9 2.037(6) . ?
Fe1 C3 2.042(7) . ?
Fe1 C4 2.044(8) . ?
Fe1 C2 2.047(8) . ?
Fe1 C8 2.056(5) . ?
Fe1 C7 2.058(6) . ?
C1 C5 1.364(12) . ?
C1 C2 1.390(11) . ?
C1 H1 0.9500 . ?
C2 C3 1.384(12) . ?
C2 H2 0.9500 . ?
C3 C4 1.382(12) . ?
C3 H3 0.9500 . ?
C4 C5 1.416(11) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.399(8) . ?
C6 C10 1.432(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.414(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.422(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.447(8) . ?
C9 C14 1.473(7) . ?
C10 S1 1.719(6) . ?
S1 O11 1.417(4) . ?
S1 O12 1.424(4) . ?
S1 F13 1.558(4) . ?
C14 N19 1.326(7) . ?
C14 C15 1.406(7) . ?
C15 C16 1.371(8) . ?
C15 H15 0.9500 . ?
C16 C17 1.381(9) . ?
C16 H16 0.9500 . ?
C17 C18 1.368(9) . ?
C17 H17 0.9500 . ?
C18 N19 1.345(7) . ?
C18 H18 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 Fe1 C1 122.4(3) . . ?
C10 Fe1 C5 155.4(3) . . ?
C1 Fe1 C5 39.4(3) . . ?
C10 Fe1 C6 41.5(2) . . ?
C1 Fe1 C6 108.2(3) . . ?
C5 Fe1 C6 119.1(3) . . ?
C10 Fe1 C9 41.9(2) . . ?
C1 Fe1 C9 157.9(3) . . ?
C5 Fe1 C9 160.9(3) . . ?
C6 Fe1 C9 70.2(2) . . ?
C10 Fe1 C3 126.9(3) . . ?
C1 Fe1 C3 66.1(3) . . ?
C5 Fe1 C3 67.2(3) . . ?
C6 Fe1 C3 163.5(3) . . ?
C9 Fe1 C3 108.9(3) . . ?
C10 Fe1 C4 162.7(3) . . ?
C1 Fe1 C4 66.6(3) . . ?
C5 Fe1 C4 40.7(3) . . ?
C6 Fe1 C4 154.5(3) . . ?
C9 Fe1 C4 124.3(3) . . ?
C3 Fe1 C4 39.5(3) . . ?
C10 Fe1 C2 109.2(3) . . ?
C1 Fe1 C2 40.0(3) . . ?
C5 Fe1 C2 67.5(3) . . ?
C6 Fe1 C2 126.1(3) . . ?
C9 Fe1 C2 122.2(3) . . ?
C3 Fe1 C2 39.6(3) . . ?
C4 Fe1 C2 67.1(3) . . ?
C10 Fe1 C8 68.7(2) . . ?
C1 Fe1 C8 160.7(3) . . ?
C5 Fe1 C8 124.2(3) . . ?
C6 Fe1 C8 68.5(2) . . ?
C9 Fe1 C8 40.6(2) . . ?
C3 Fe1 C8 122.2(3) . . ?
C4 Fe1 C8 107.7(3) . . ?
C2 Fe1 C8 157.0(3) . . ?
C10 Fe1 C7 68.0(2) . . ?
C1 Fe1 C7 125.3(3) . . ?
C5 Fe1 C7 107.2(3) . . ?
C6 Fe1 C7 40.0(2) . . ?
C9 Fe1 C7 68.4(2) . . ?
C3 Fe1 C7 156.1(3) . . ?
C4 Fe1 C7 121.0(3) . . ?
C2 Fe1 C7 162.0(3) . . ?
C8 Fe1 C7 40.2(2) . . ?
C5 C1 C2 110.6(9) . . ?
C5 C1 Fe1 70.6(5) . . ?
C2 C1 Fe1 71.0(4) . . ?
C5 C1 H1 124.7 . . ?
C2 C1 H1 124.7 . . ?
Fe1 C1 H1 125.2 . . ?
C3 C2 C1 106.0(9) . . ?
C3 C2 Fe1 70.0(5) . . ?
C1 C2 Fe1 69.0(5) . . ?
C3 C2 H2 127.0 . . ?
C1 C2 H2 127.0 . . ?
Fe1 C2 H2 125.6 . . ?
C4 C3 C2 109.6(8) . . ?
C4 C3 Fe1 70.3(4) . . ?
C2 C3 Fe1 70.4(5) . . ?
C4 C3 H3 125.2 . . ?
C2 C3 H3 125.2 . . ?
Fe1 C3 H3 125.7 . . ?
C3 C4 C5 107.1(8) . . ?
C3 C4 Fe1 70.1(5) . . ?
C5 C4 Fe1 69.1(4) . . ?
C3 C4 H4 126.4 . . ?
C5 C4 H4 126.4 . . ?
Fe1 C4 H4 125.9 . . ?
C1 C5 C4 106.7(8) . . ?
C1 C5 Fe1 70.0(5) . . ?
C4 C5 Fe1 70.2(5) . . ?
C1 C5 H5 126.7 . . ?
C4 C5 H5 126.6 . . ?
Fe1 C5 H5 124.7 . . ?
C7 C6 C10 106.7(5) . . ?
C7 C6 Fe1 71.0(3) . . ?
C10 C6 Fe1 68.2(3) . . ?
C7 C6 H6 126.6 . . ?
C10 C6 H6 126.6 . . ?
Fe1 C6 H6 125.7 . . ?
C6 C7 C8 109.8(5) . . ?
C6 C7 Fe1 69.1(3) . . ?
C8 C7 Fe1 69.8(3) . . ?
C6 C7 H7 125.1 . . ?
C8 C7 H7 125.1 . . ?
Fe1 C7 H7 127.7 . . ?
C7 C8 C9 108.6(5) . . ?
C7 C8 Fe1 70.0(3) . . ?
C9 C8 Fe1 69.0(3) . . ?
C7 C8 H8 125.7 . . ?
C9 C8 H8 125.7 . . ?
Fe1 C8 H8 126.9 . . ?
C8 C9 C10 106.0(5) . . ?
C8 C9 C14 125.3(5) . . ?
C10 C9 C14 128.4(5) . . ?
C8 C9 Fe1 70.4(3) . . ?
C10 C9 Fe1 67.9(3) . . ?
C14 C9 Fe1 130.6(4) . . ?
C6 C10 C9 108.8(5) . . ?
C6 C10 S1 121.3(4) . . ?
C9 C10 S1 129.6(4) . . ?
C6 C10 Fe1 70.2(3) . . ?
C9 C10 Fe1 70.2(3) . . ?
S1 C10 Fe1 120.7(3) . . ?
O11 S1 O12 119.6(3) . . ?
O11 S1 F13 106.2(2) . . ?
O12 S1 F13 104.7(2) . . ?
O11 S1 C10 113.6(3) . . ?
O12 S1 C10 109.1(3) . . ?
F13 S1 C10 101.7(2) . . ?
N19 C14 C15 122.7(5) . . ?
N19 C14 C9 117.0(5) . . ?
C15 C14 C9 120.2(5) . . ?
C16 C15 C14 118.2(5) . . ?
C16 C15 H15 120.9 . . ?
C14 C15 H15 120.9 . . ?
C15 C16 C17 119.4(5) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C18 C17 C16 118.4(6) . . ?
C18 C17 H17 120.8 . . ?
C16 C17 H17 120.8 . . ?
N19 C18 C17 123.7(6) . . ?
N19 C18 H18 118.1 . . ?
C17 C18 H18 118.1 . . ?
C14 N19 C18 117.4(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
C5 C1 C2 C3 0.8(8) . . . . ?
Fe1 C1 C2 C3 60.6(5) . . . . ?
C5 C1 C2 Fe1 -59.8(5) . . . . ?
C1 C2 C3 C4 -0.4(8) . . . . ?
Fe1 C2 C3 C4 59.6(5) . . . . ?
C1 C2 C3 Fe1 -59.9(5) . . . . ?
C2 C3 C4 C5 -0.2(8) . . . . ?
Fe1 C3 C4 C5 59.4(5) . . . . ?
C2 C3 C4 Fe1 -59.6(5) . . . . ?
C2 C1 C5 C4 -1.0(8) . . . . ?
Fe1 C1 C5 C4 -61.0(5) . . . . ?
C2 C1 C5 Fe1 60.0(5) . . . . ?
C3 C4 C5 C1 0.7(8) . . . . ?
Fe1 C4 C5 C1 60.8(5) . . . . ?
C3 C4 C5 Fe1 -60.1(5) . . . . ?
C10 C6 C7 C8 -1.1(6) . . . . ?
Fe1 C6 C7 C8 57.9(4) . . . . ?
C10 C6 C7 Fe1 -59.1(3) . . . . ?
C6 C7 C8 C9 0.8(6) . . . . ?
Fe1 C7 C8 C9 58.3(4) . . . . ?
C6 C7 C8 Fe1 -57.5(4) . . . . ?
C7 C8 C9 C10 -0.1(6) . . . . ?
Fe1 C8 C9 C10 58.8(4) . . . . ?
C7 C8 C9 C14 174.7(5) . . . . ?
Fe1 C8 C9 C14 -126.4(5) . . . . ?
C7 C8 C9 Fe1 -58.9(4) . . . . ?
C7 C6 C10 C9 1.1(6) . . . . ?
Fe1 C6 C10 C9 -59.8(4) . . . . ?
C7 C6 C10 S1 175.5(4) . . . . ?
Fe1 C6 C10 S1 114.7(4) . . . . ?
C7 C6 C10 Fe1 60.9(4) . . . . ?
C8 C9 C10 C6 -0.6(6) . . . . ?
C14 C9 C10 C6 -175.2(5) . . . . ?
Fe1 C9 C10 C6 59.8(4) . . . . ?
C8 C9 C10 S1 -174.4(4) . . . . ?
C14 C9 C10 S1 11.0(9) . . . . ?
Fe1 C9 C10 S1 -114.0(5) . . . . ?
C8 C9 C10 Fe1 -60.4(4) . . . . ?
C14 C9 C10 Fe1 125.0(5) . . . . ?
C6 C10 S1 O11 -145.3(4) . . . . ?
C9 C10 S1 O11 27.9(6) . . . . ?
Fe1 C10 S1 O11 -61.0(4) . . . . ?
C6 C10 S1 O12 -9.2(5) . . . . ?
C9 C10 S1 O12 164.0(5) . . . . ?
Fe1 C10 S1 O12 75.1(4) . . . . ?
C6 C10 S1 F13 101.0(4) . . . . ?
C9 C10 S1 F13 -85.8(5) . . . . ?
Fe1 C10 S1 F13 -174.7(3) . . . . ?
C8 C9 C14 N19 -140.8(6) . . . . ?
C10 C9 C14 N19 32.8(8) . . . . ?
Fe1 C9 C14 N19 125.5(5) . . . . ?
C8 C9 C14 C15 35.9(8) . . . . ?
C10 C9 C14 C15 -150.4(6) . . . . ?
Fe1 C9 C14 C15 -57.8(7) . . . . ?
N19 C14 C15 C16 0.5(8) . . . . ?
C9 C14 C15 C16 -176.0(5) . . . . ?
C14 C15 C16 C17 0.0(8) . . . . ?
C15 C16 C17 C18 -0.2(9) . . . . ?
C16 C17 C18 N19 -0.1(10) . . . . ?
C15 C14 N19 C18 -0.8(8) . . . . ?
C9 C14 N19 C18 175.8(5) . . . . ?
C17 C18 N19 C14 0.6(9) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


####################################################################### 
# 
# 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_WE18201
_database_code_depnum_ccdc_archive 'CCDC 2189755'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;ISCR
France
;
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2022-09-25 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 07 fevrier 2022                                          #
#------------------------------------------------------------------------------#


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H12 Cl F Fe O2 S2'
_chemical_formula_sum            'C16 H12 Cl F Fe O2 S2'
_chemical_formula_weight         410.68
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.426(3)
_cell_length_b                   11.340(2)
_cell_length_c                   11.384(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.083(7)
_cell_angle_gamma                90
_cell_volume                     1584.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5077
_cell_measurement_theta_min      2.5512
_cell_measurement_theta_max      27.5041
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      -0.0152649
_diffrn_orient_matrix_UB_21      -0.0250065
_diffrn_orient_matrix_UB_31      0.0839989
_diffrn_orient_matrix_UB_12      0.0136938
_diffrn_orient_matrix_UB_22      0.0827779
_diffrn_orient_matrix_UB_32      0.0271315
_diffrn_orient_matrix_UB_13      -0.0804985
_diffrn_orient_matrix_UB_23      0.0124324
_diffrn_orient_matrix_UB_33      0.0026982


#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.220
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.722
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             832
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.620
_exptl_absorpt_correction_T_max  0.735

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

# Software                   : BIS 2014.5.0.0/23-May-2014 && APEX2_2014.11-0   #
# Number of scans            :        4                                        #
# Total number of frames     :      372                                        #
# Total length of scans      :   372.00 (deg.)                                 #
# Rotation speed             :     4.00 sec./deg.                              #
# Total exposition time      :         24.8 min.                               #
#                                                                              #
#    Scan  Time(s) Width DX(mm) Frames Range 2Theta  Omega    Phi    Chi  T(K) #
#..............................................................................#
#                                                                              #
#  1 Omega    4.0  1.00    35.0    93   93.0  344.0  344.6   32.3  -31.3 150.0 #
#  2 Omega    4.0  1.00    35.0    93   93.0  344.0  341.0  308.3  -23.3 150.0 #
#  3 Omega    4.0  1.00    35.0    93   93.0  344.0  344.6   32.3  -31.3 150.0 #
#  4 Omega    4.0  1.00    35.0    93   93.0  344.0  341.0  308.3  -23.3 150.0 #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'APEXII Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 CCD-LDI-APEX2
_diffrn_detector_area_resol_mean 8.33
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_source_current           30.00
_diffrn_source_voltage           50.00
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0342
_diffrn_reflns_av_r_equivalents  0.0383
_diffrn_reflns_number            17052
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.884
_diffrn_reflns_theta_max         27.515
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_reflns_number_total             3618
_reflns_number_gt                3041
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2021)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0496P)²+0.4157P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         3618
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0869
_refine_ls_wR_factor_gt          0.0812
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.072

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'
Cl Cl 0.1484 0.1585 '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'
Fe Fe 0.3463 0.8444 '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'

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 0.67946(2) 0.44598(2) 0.26211(2) 0.01335(10) Uani 1 1 d . . . . .
Cl1 Cl 0.44400(4) 0.57307(6) 0.31287(6) 0.03287(16) Uani 1 1 d . . . . .
S1 S 0.69672(4) 0.69096(5) 0.42204(5) 0.02179(14) Uani 1 1 d . . . . .
S2 S 0.88279(4) 0.44411(5) 0.48448(5) 0.02045(14) Uani 1 1 d . . . . .
C1 C 0.63466(18) 0.3842(2) 0.09356(18) 0.0231(5) Uani 1 1 d . . . . .
H1 H 0.572350 0.337265 0.066353 0.028 Uiso 1 1 calc R U . . .
C2 C 0.73976(18) 0.3414(2) 0.14219(18) 0.0235(5) Uani 1 1 d . . . . .
H2 H 0.759886 0.260918 0.153532 0.028 Uiso 1 1 calc R U . . .
C3 C 0.80944(18) 0.43987(19) 0.17087(19) 0.0228(5) Uani 1 1 d . . . . .
H3 H 0.884407 0.436796 0.204405 0.027 Uiso 1 1 calc R U . . .
C4 C 0.74782(19) 0.5432(2) 0.14082(19) 0.0237(5) Uani 1 1 d . . . . .
H4 H 0.774240 0.621766 0.150888 0.028 Uiso 1 1 calc R U . . .
C5 C 0.63914(18) 0.5096(2) 0.09277(18) 0.0231(5) Uani 1 1 d . . . . .
H5 H 0.580485 0.561376 0.065277 0.028 Uiso 1 1 calc R U . . .
C6 C 0.56302(16) 0.49514(19) 0.35676(18) 0.0196(4) Uani 1 1 d . . . . .
C7 C 0.66805(16) 0.54275(17) 0.40539(18) 0.0161(4) Uani 1 1 d . . . . .
C8 C 0.74100(16) 0.44377(18) 0.43705(17) 0.0164(4) Uani 1 1 d . . . . .
C9 C 0.67886(17) 0.33998(19) 0.40670(18) 0.0200(4) Uani 1 1 d . . . . .
H9 H 0.705766 0.261639 0.417128 0.024 Uiso 1 1 calc R U . . .
C10 C 0.57009(17) 0.37152(19) 0.35827(18) 0.0211(4) Uani 1 1 d . . . . .
H10 H 0.512338 0.318294 0.331627 0.025 Uiso 1 1 calc R U . . .
F11 F 0.63973(14) 0.71581(13) 0.53279(15) 0.0511(5) Uani 1 1 d . . . . .
O12 O 0.80816(13) 0.71195(14) 0.46157(16) 0.0353(4) Uani 1 1 d . . . . .
O13 O 0.63907(17) 0.75812(15) 0.32980(17) 0.0512(6) Uani 1 1 d . . . . .
C14 C 0.89466(16) 0.42623(18) 0.64173(18) 0.0185(4) Uani 1 1 d . . . . .
C15 C 0.83632(19) 0.4935(2) 0.7112(2) 0.0278(5) Uani 1 1 d . . . . .
H15 H 0.787434 0.552421 0.675500 0.033 Uiso 1 1 calc R U . . .
C16 C 0.8493(2) 0.4749(2) 0.8337(2) 0.0362(6) Uani 1 1 d . . . . .
H16 H 0.807791 0.519629 0.881146 0.043 Uiso 1 1 calc R U . . .
C17 C 0.9227(2) 0.3913(2) 0.8862(2) 0.0356(6) Uani 1 1 d . . . . .
H17 H 0.931705 0.378953 0.969673 0.043 Uiso 1 1 calc R U . . .
C18 C 0.98287(19) 0.3258(2) 0.8176(2) 0.0301(5) Uani 1 1 d . . . . .
H18 H 1.033710 0.269109 0.854199 0.036 Uiso 1 1 calc R U . . .
C19 C 0.96926(17) 0.3425(2) 0.69470(19) 0.0236(5) Uani 1 1 d . . . . .
H19 H 1.010480 0.297258 0.647425 0.028 Uiso 1 1 calc R U . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_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 1.989(2) . ?
Fe1 C6 2.014(2) . ?
Fe1 C8 2.018(2) . ?
Fe1 C1 2.036(2) . ?
Fe1 C9 2.039(2) . ?
Fe1 C2 2.038(2) . ?
Fe1 C5 2.045(2) . ?
Fe1 C4 2.053(2) . ?
Fe1 C3 2.055(2) . ?
Fe1 C10 2.056(2) . ?
Cl1 C6 1.728(2) . ?
S1 O13 1.3993(18) . ?
S1 O12 1.4070(17) . ?
S1 F11 1.5660(15) . ?
S1 C7 1.722(2) . ?
S2 C8 1.759(2) . ?
S2 C14 1.784(2) . ?
C1 C2 1.421(3) . ?
C1 C5 1.423(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.419(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.412(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.427(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C10 1.405(3) . ?
C6 C7 1.440(3) . ?
C7 C8 1.452(3) . ?
C8 C9 1.420(3) . ?
C9 C10 1.423(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C14 C15 1.384(3) . ?
C14 C19 1.396(3) . ?
C15 C16 1.394(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.380(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.396(3) . ?
C18 H18 0.9500 . ?
C19 H19 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
C7 Fe1 C6 42.15(8) . . ?
C7 Fe1 C8 42.49(8) . . ?
C6 Fe1 C8 70.60(8) . . ?
C7 Fe1 C1 156.67(9) . . ?
C6 Fe1 C1 119.13(9) . . ?
C8 Fe1 C1 158.52(9) . . ?
C7 Fe1 C9 69.73(9) . . ?
C6 Fe1 C9 68.71(9) . . ?
C8 Fe1 C9 40.98(8) . . ?
C1 Fe1 C9 121.49(9) . . ?
C7 Fe1 C2 162.07(8) . . ?
C6 Fe1 C2 152.92(9) . . ?
C8 Fe1 C2 122.13(8) . . ?
C1 Fe1 C2 40.82(8) . . ?
C9 Fe1 C2 104.26(9) . . ?
C7 Fe1 C5 122.67(9) . . ?
C6 Fe1 C5 108.47(9) . . ?
C8 Fe1 C5 158.93(9) . . ?
C1 Fe1 C5 40.82(9) . . ?
C9 Fe1 C5 159.58(9) . . ?
C2 Fe1 C5 68.59(9) . . ?
C7 Fe1 C4 110.23(9) . . ?
C6 Fe1 C4 128.28(9) . . ?
C8 Fe1 C4 122.55(9) . . ?
C1 Fe1 C4 68.39(9) . . ?
C9 Fe1 C4 156.09(9) . . ?
C2 Fe1 C4 68.11(10) . . ?
C5 Fe1 C4 40.75(9) . . ?
C7 Fe1 C3 126.62(9) . . ?
C6 Fe1 C3 165.48(9) . . ?
C8 Fe1 C3 107.03(9) . . ?
C1 Fe1 C3 68.40(9) . . ?
C9 Fe1 C3 119.44(9) . . ?
C2 Fe1 C3 40.57(9) . . ?
C5 Fe1 C3 68.32(9) . . ?
C4 Fe1 C3 40.21(9) . . ?
C7 Fe1 C10 69.60(8) . . ?
C6 Fe1 C10 40.36(9) . . ?
C8 Fe1 C10 69.44(8) . . ?
C1 Fe1 C10 104.77(9) . . ?
C9 Fe1 C10 40.65(8) . . ?
C2 Fe1 C10 117.48(9) . . ?
C5 Fe1 C10 124.22(9) . . ?
C4 Fe1 C10 163.16(9) . . ?
C3 Fe1 C10 153.33(9) . . ?
O13 S1 O12 120.62(12) . . ?
O13 S1 F11 105.26(12) . . ?
O12 S1 F11 105.03(10) . . ?
O13 S1 C7 112.09(10) . . ?
O12 S1 C7 112.10(10) . . ?
F11 S1 C7 98.76(9) . . ?
C8 S2 C14 103.17(10) . . ?
C2 C1 C5 107.99(19) . . ?
C2 C1 Fe1 69.67(12) . . ?
C5 C1 Fe1 69.92(12) . . ?
C2 C1 H1 126.0 . . ?
C5 C1 H1 126.0 . . ?
Fe1 C1 H1 126.0 . . ?
C3 C2 C1 108.1(2) . . ?
C3 C2 Fe1 70.34(13) . . ?
C1 C2 Fe1 69.52(12) . . ?
C3 C2 H2 125.9 . . ?
C1 C2 H2 125.9 . . ?
Fe1 C2 H2 125.8 . . ?
C4 C3 C2 108.0(2) . . ?
C4 C3 Fe1 69.82(13) . . ?
C2 C3 Fe1 69.09(12) . . ?
C4 C3 H3 126.0 . . ?
C2 C3 H3 126.0 . . ?
Fe1 C3 H3 126.7 . . ?
C3 C4 C5 108.4(2) . . ?
C3 C4 Fe1 69.96(13) . . ?
C5 C4 Fe1 69.33(12) . . ?
C3 C4 H4 125.8 . . ?
C5 C4 H4 125.8 . . ?
Fe1 C4 H4 126.5 . . ?
C1 C5 C4 107.49(19) . . ?
C1 C5 Fe1 69.25(11) . . ?
C4 C5 Fe1 69.92(12) . . ?
C1 C5 H5 126.3 . . ?
C4 C5 H5 126.3 . . ?
Fe1 C5 H5 126.1 . . ?
C10 C6 C7 108.57(18) . . ?
C10 C6 Cl1 124.27(16) . . ?
C7 C6 Cl1 127.01(17) . . ?
C10 C6 Fe1 71.43(12) . . ?
C7 C6 Fe1 68.00(12) . . ?
Cl1 C6 Fe1 129.89(12) . . ?
C6 C7 C8 107.34(17) . . ?
C6 C7 S1 124.57(16) . . ?
C8 C7 S1 128.09(15) . . ?
C6 C7 Fe1 69.85(11) . . ?
C8 C7 Fe1 69.79(11) . . ?
S1 C7 Fe1 126.03(12) . . ?
C9 C8 C7 106.63(17) . . ?
C9 C8 S2 123.79(16) . . ?
C7 C8 S2 129.06(15) . . ?
C9 C8 Fe1 70.33(11) . . ?
C7 C8 Fe1 67.72(11) . . ?
S2 C8 Fe1 120.53(11) . . ?
C8 C9 C10 109.43(19) . . ?
C8 C9 Fe1 68.69(12) . . ?
C10 C9 Fe1 70.32(12) . . ?
C8 C9 H9 125.3 . . ?
C10 C9 H9 125.3 . . ?
Fe1 C9 H9 127.3 . . ?
C6 C10 C9 108.02(18) . . ?
C6 C10 Fe1 68.21(12) . . ?
C9 C10 Fe1 69.03(12) . . ?
C6 C10 H10 126.0 . . ?
C9 C10 H10 126.0 . . ?
Fe1 C10 H10 128.3 . . ?
C15 C14 C19 120.0(2) . . ?
C15 C14 S2 122.90(17) . . ?
C19 C14 S2 117.06(17) . . ?
C14 C15 C16 120.0(2) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 120.0(2) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C18 C17 C16 120.3(2) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 120.2(2) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C14 119.5(2) . . ?
C18 C19 H19 120.2 . . ?
C14 C19 H19 120.2 . . ?

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
C5 C1 C2 C3 -0.3(2) . . . . ?
Fe1 C1 C2 C3 -59.99(15) . . . . ?
C5 C1 C2 Fe1 59.65(14) . . . . ?
C1 C2 C3 C4 0.3(2) . . . . ?
Fe1 C2 C3 C4 -59.16(16) . . . . ?
C1 C2 C3 Fe1 59.47(15) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
Fe1 C3 C4 C5 -58.87(15) . . . . ?
C2 C3 C4 Fe1 58.70(15) . . . . ?
C2 C1 C5 C4 0.2(2) . . . . ?
Fe1 C1 C5 C4 59.72(15) . . . . ?
C2 C1 C5 Fe1 -59.49(14) . . . . ?
C3 C4 C5 C1 0.0(2) . . . . ?
Fe1 C4 C5 C1 -59.30(14) . . . . ?
C3 C4 C5 Fe1 59.26(15) . . . . ?
C10 C6 C7 C8 0.1(2) . . . . ?
Cl1 C6 C7 C8 175.83(16) . . . . ?
Fe1 C6 C7 C8 -60.00(14) . . . . ?
C10 C6 C7 S1 -179.33(16) . . . . ?
Cl1 C6 C7 S1 -3.6(3) . . . . ?
Fe1 C6 C7 S1 120.54(17) . . . . ?
C10 C6 C7 Fe1 60.13(15) . . . . ?
Cl1 C6 C7 Fe1 -124.17(18) . . . . ?
O13 S1 C7 C6 -35.2(2) . . . . ?
O12 S1 C7 C6 -174.51(18) . . . . ?
F11 S1 C7 C6 75.26(19) . . . . ?
O13 S1 C7 C8 145.4(2) . . . . ?
O12 S1 C7 C8 6.1(2) . . . . ?
F11 S1 C7 C8 -104.1(2) . . . . ?
O13 S1 C7 Fe1 53.87(18) . . . . ?
O12 S1 C7 Fe1 -85.42(15) . . . . ?
F11 S1 C7 Fe1 164.35(13) . . . . ?
C6 C7 C8 C9 0.2(2) . . . . ?
S1 C7 C8 C9 179.61(16) . . . . ?
Fe1 C7 C8 C9 -59.87(14) . . . . ?
C6 C7 C8 S2 172.03(16) . . . . ?
S1 C7 C8 S2 -8.5(3) . . . . ?
Fe1 C7 C8 S2 112.00(18) . . . . ?
C6 C7 C8 Fe1 60.04(14) . . . . ?
S1 C7 C8 Fe1 -120.53(18) . . . . ?
C14 S2 C8 C9 -88.50(19) . . . . ?
C14 S2 C8 C7 100.9(2) . . . . ?
C14 S2 C8 Fe1 -174.17(11) . . . . ?
C7 C8 C9 C10 -0.4(2) . . . . ?
S2 C8 C9 C10 -172.81(15) . . . . ?
Fe1 C8 C9 C10 -58.61(14) . . . . ?
C7 C8 C9 Fe1 58.20(14) . . . . ?
S2 C8 C9 Fe1 -114.20(16) . . . . ?
C7 C6 C10 C9 -0.4(2) . . . . ?
Cl1 C6 C10 C9 -176.23(15) . . . . ?
Fe1 C6 C10 C9 57.63(14) . . . . ?
C7 C6 C10 Fe1 -58.01(14) . . . . ?
Cl1 C6 C10 Fe1 126.14(17) . . . . ?
C8 C9 C10 C6 0.5(2) . . . . ?
Fe1 C9 C10 C6 -57.13(14) . . . . ?
C8 C9 C10 Fe1 57.63(14) . . . . ?
C8 S2 C14 C15 -49.0(2) . . . . ?
C8 S2 C14 C19 133.07(16) . . . . ?
C19 C14 C15 C16 -2.2(3) . . . . ?
S2 C14 C15 C16 179.90(19) . . . . ?
C14 C15 C16 C17 1.7(4) . . . . ?
C15 C16 C17 C18 -0.3(4) . . . . ?
C16 C17 C18 C19 -0.7(4) . . . . ?
C17 C18 C19 C14 0.2(3) . . . . ?
C15 C14 C19 C18 1.2(3) . . . . ?
S2 C14 C19 C18 179.25(17) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


####################################################################### 
# 
# 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_WE17201
_database_code_depnum_ccdc_archive 'CCDC 2189754'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;ISCR
France
;
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2022-09-25 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 28 octobre 2021                                          #
#------------------------------------------------------------------------------#


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H12 F Fe I O2 S2'
_chemical_formula_sum            'C16 H12 F Fe I O2 S2'
_chemical_formula_weight         502.13
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.540(3)
_cell_length_b                   10.7796(13)
_cell_length_c                   15.5376(17)
_cell_angle_alpha                90
_cell_angle_beta                 90.036(4)
_cell_angle_gamma                90
_cell_volume                     3440.2(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9893
_cell_measurement_theta_min      2.5040
_cell_measurement_theta_max      27.4559
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      0.0350449
_diffrn_orient_matrix_UB_21      -0.0328581
_diffrn_orient_matrix_UB_31      0.0079071
_diffrn_orient_matrix_UB_12      0.0591056
_diffrn_orient_matrix_UB_22      0.0509730
_diffrn_orient_matrix_UB_32      -0.0501415
_diffrn_orient_matrix_UB_13      0.0177633
_diffrn_orient_matrix_UB_23      0.0316727
_diffrn_orient_matrix_UB_33      0.0531369


#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.050
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.939
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1952
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.674
_exptl_absorpt_correction_T_max  0.864

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

# Software                   : BIS V6.2.15/2021-03-15 && APEX3 2016.9-0        #
# Number of scans            :        4                                        #
# Total number of frames     :      291                                        #
# Total length of scans      :   291.00 (deg.)                                 #
# Rotation speed             :     5.00 sec./deg.                              #
# Total exposition time      :         24.2 min.                               #
#                                                                              #
#    Scan  Time(s) Width DX(mm) Frames Range 2Theta  Omega    Phi    Chi  T(K) #
#..............................................................................#
#                                                                              #
#  1 Omega    5.0  1.00    34.0    97   97.0    1.9    4.5   72.0  315.5 150.0 #
#  2 Omega    5.0  1.00    34.0    97   97.0    1.9    4.5  216.0  315.5 150.0 #
#  3 Omega    5.0  1.00    34.0    97   97.0    1.9    4.5    0.0  315.5 150.0 #
#  4 Fast     1.0  1.00    34.0   180  180.0    0.0  360.0    0.0   54.7 150.0 #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.00
_diffrn_source_voltage           50.00
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0280
_diffrn_reflns_av_r_equivalents  0.0368
_diffrn_reflns_number            19639
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.983
_diffrn_reflns_theta_max         27.466
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             3935
_reflns_number_gt                3701
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2021)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0162P)²+4.7913P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         3935
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0214
_refine_ls_R_factor_gt           0.0195
_refine_ls_wR_factor_ref         0.0469
_refine_ls_wR_factor_gt          0.0457
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.084

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'
F F 0.0171 0.0103 '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'
I I -0.4742 1.8119 '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'

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 0.66581(2) 0.48771(2) 0.59253(2) 0.01318(6) Uani 1 1 d . . . . .
I1 I 0.60617(2) 0.58504(2) 0.80784(2) 0.02244(5) Uani 1 1 d . . . . .
C1 C 0.74258(10) 0.4432(2) 0.51351(14) 0.0269(4) Uani 1 1 d . . . . .
H1 H 0.743214 0.380052 0.470880 0.032 Uiso 1 1 calc R U . . .
C2 C 0.76073(10) 0.4288(2) 0.60081(15) 0.0274(4) Uani 1 1 d . . . . .
H2 H 0.775615 0.354405 0.626967 0.033 Uiso 1 1 calc R U . . .
C3 C 0.75283(10) 0.5450(2) 0.64245(14) 0.0275(4) Uani 1 1 d . . . . .
H3 H 0.761521 0.561995 0.701335 0.033 Uiso 1 1 calc R U . . .
C4 C 0.72964(10) 0.63123(19) 0.58052(15) 0.0280(4) Uani 1 1 d . . . . .
H4 H 0.720037 0.716207 0.590603 0.034 Uiso 1 1 calc R U . . .
C5 C 0.72334(10) 0.5677(2) 0.50070(14) 0.0276(4) Uani 1 1 d . . . . .
H5 H 0.708767 0.602771 0.448016 0.033 Uiso 1 1 calc R U . . .
C6 C 0.59847(9) 0.50085(16) 0.68734(11) 0.0158(3) Uani 1 1 d . . . . .
C7 C 0.57628(9) 0.56862(16) 0.61489(12) 0.0170(3) Uani 1 1 d . . . . .
H7 H 0.565028 0.654105 0.614791 0.020 Uiso 1 1 calc R U . . .
C8 C 0.57353(9) 0.48860(16) 0.54261(12) 0.0159(3) Uani 1 1 d . . . . .
H8 H 0.560568 0.512111 0.486217 0.019 Uiso 1 1 calc R U . . .
C9 C 0.59332(8) 0.36712(16) 0.56798(11) 0.0144(3) Uani 1 1 d . . . . .
C10 C 0.60890(8) 0.37407(16) 0.65951(11) 0.0144(3) Uani 1 1 d . . . . .
O11 O 0.66827(9) 0.30285(14) 0.79777(10) 0.0376(4) Uani 1 1 d . . . . .
O12 O 0.67108(9) 0.16412(13) 0.67243(10) 0.0330(4) Uani 1 1 d . . . . .
S1 S 0.63949(2) 0.25588(4) 0.72195(3) 0.02114(10) Uani 1 1 d . . . . .
F13 F 0.57437(7) 0.19377(12) 0.75188(9) 0.0410(3) Uani 1 1 d . . . . .
S2 S 0.60228(2) 0.24120(4) 0.49731(3) 0.01671(9) Uani 1 1 d . . . . .
C14 C 0.52104(9) 0.19057(15) 0.48026(12) 0.0162(3) Uani 1 1 d . . . . .
C15 C 0.47044(9) 0.21117(17) 0.53808(12) 0.0202(4) Uani 1 1 d . . . . .
H15 H 0.477747 0.257289 0.589280 0.024 Uiso 1 1 calc R U . . .
C16 C 0.40890(10) 0.16329(18) 0.51990(14) 0.0257(4) Uani 1 1 d . . . . .
H16 H 0.373982 0.177840 0.558667 0.031 Uiso 1 1 calc R U . . .
C17 C 0.39820(10) 0.09480(18) 0.44597(16) 0.0281(5) Uani 1 1 d . . . . .
H17 H 0.356212 0.061775 0.434423 0.034 Uiso 1 1 calc R U . . .
C18 C 0.44856(11) 0.07452(18) 0.38907(15) 0.0286(5) Uani 1 1 d . . . . .
H18 H 0.441124 0.027606 0.338244 0.034 Uiso 1 1 calc R U . . .
C19 C 0.51011(10) 0.12233(17) 0.40563(13) 0.0222(4) Uani 1 1 d . . . . .
H19 H 0.544630 0.108470 0.366127 0.027 Uiso 1 1 calc R U . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_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 C10 1.9878(17) . ?
Fe1 C9 2.0129(17) . ?
Fe1 C6 2.0262(18) . ?
Fe1 C4 2.0365(19) . ?
Fe1 C3 2.043(2) . ?
Fe1 C5 2.044(2) . ?
Fe1 C8 2.0476(18) . ?
Fe1 C1 2.056(2) . ?
Fe1 C2 2.054(2) . ?
Fe1 C7 2.0649(18) . ?
I1 C6 2.0865(17) . ?
C1 C5 1.413(3) . ?
C1 C2 1.415(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.418(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.420(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.423(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.417(3) . ?
C6 C10 1.449(2) . ?
C7 C8 1.417(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.427(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.459(2) . ?
C9 S2 1.7556(18) . ?
C10 S1 1.7201(18) . ?
O11 S1 1.4116(16) . ?
O12 S1 1.4113(15) . ?
S1 F13 1.5667(14) . ?
S2 C14 1.7752(18) . ?
C14 C19 1.391(3) . ?
C14 C15 1.392(3) . ?
C15 C16 1.394(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.383(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.379(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.389(3) . ?
C18 H18 0.9500 . ?
C19 H19 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 Fe1 C9 42.78(7) . . ?
C10 Fe1 C6 42.32(7) . . ?
C9 Fe1 C6 71.20(7) . . ?
C10 Fe1 C4 153.50(8) . . ?
C9 Fe1 C4 161.70(8) . . ?
C6 Fe1 C4 116.95(8) . . ?
C10 Fe1 C3 120.13(8) . . ?
C9 Fe1 C3 156.02(8) . . ?
C6 Fe1 C3 107.47(8) . . ?
C4 Fe1 C3 40.74(9) . . ?
C10 Fe1 C5 164.97(8) . . ?
C9 Fe1 C5 124.61(8) . . ?
C6 Fe1 C5 150.84(8) . . ?
C4 Fe1 C5 40.81(9) . . ?
C3 Fe1 C5 68.38(9) . . ?
C10 Fe1 C8 69.92(7) . . ?
C9 Fe1 C8 41.13(7) . . ?
C6 Fe1 C8 69.08(7) . . ?
C4 Fe1 C8 123.89(8) . . ?
C3 Fe1 C8 162.12(8) . . ?
C5 Fe1 C8 105.61(8) . . ?
C10 Fe1 C1 128.34(8) . . ?
C9 Fe1 C1 107.68(8) . . ?
C6 Fe1 C1 167.08(8) . . ?
C4 Fe1 C1 68.19(9) . . ?
C3 Fe1 C1 68.04(9) . . ?
C5 Fe1 C1 40.31(9) . . ?
C8 Fe1 C1 119.01(8) . . ?
C10 Fe1 C2 109.59(8) . . ?
C9 Fe1 C2 120.95(8) . . ?
C6 Fe1 C2 128.63(8) . . ?
C4 Fe1 C2 68.25(9) . . ?
C3 Fe1 C2 40.50(9) . . ?
C5 Fe1 C2 67.96(9) . . ?
C8 Fe1 C2 154.61(8) . . ?
C1 Fe1 C2 40.27(9) . . ?
C10 Fe1 C7 69.40(7) . . ?
C9 Fe1 C7 69.26(7) . . ?
C6 Fe1 C7 40.51(7) . . ?
C4 Fe1 C7 105.54(8) . . ?
C3 Fe1 C7 125.98(8) . . ?
C5 Fe1 C7 117.05(8) . . ?
C8 Fe1 C7 40.32(7) . . ?
C1 Fe1 C7 151.95(9) . . ?
C2 Fe1 C7 164.84(8) . . ?
C5 C1 C2 108.21(19) . . ?
C5 C1 Fe1 69.39(11) . . ?
C2 C1 Fe1 69.81(11) . . ?
C5 C1 H1 125.9 . . ?
C2 C1 H1 125.9 . . ?
Fe1 C1 H1 126.5 . . ?
C1 C2 C3 108.10(19) . . ?
C1 C2 Fe1 69.92(12) . . ?
C3 C2 Fe1 69.34(11) . . ?
C1 C2 H2 126.0 . . ?
C3 C2 H2 126.0 . . ?
Fe1 C2 H2 126.4 . . ?
C2 C3 C4 107.89(19) . . ?
C2 C3 Fe1 70.16(11) . . ?
C4 C3 Fe1 69.37(11) . . ?
C2 C3 H3 126.1 . . ?
C4 C3 H3 126.1 . . ?
Fe1 C3 H3 126.0 . . ?
C3 C4 C5 107.79(19) . . ?
C3 C4 Fe1 69.89(11) . . ?
C5 C4 Fe1 69.87(11) . . ?
C3 C4 H4 126.1 . . ?
C5 C4 H4 126.1 . . ?
Fe1 C4 H4 125.7 . . ?
C1 C5 C4 108.01(19) . . ?
C1 C5 Fe1 70.30(11) . . ?
C4 C5 Fe1 69.31(11) . . ?
C1 C5 H5 126.0 . . ?
C4 C5 H5 126.0 . . ?
Fe1 C5 H5 126.0 . . ?
C7 C6 C10 107.26(15) . . ?
C7 C6 Fe1 71.21(10) . . ?
C10 C6 Fe1 67.43(10) . . ?
C7 C6 I1 120.85(13) . . ?
C10 C6 I1 131.81(13) . . ?
Fe1 C6 I1 129.15(9) . . ?
C6 C7 C8 109.17(15) . . ?
C6 C7 Fe1 68.27(10) . . ?
C8 C7 Fe1 69.18(10) . . ?
C6 C7 H7 125.4 . . ?
C8 C7 H7 125.4 . . ?
Fe1 C7 H7 128.8 . . ?
C7 C8 C9 109.18(16) . . ?
C7 C8 Fe1 70.50(10) . . ?
C9 C8 Fe1 68.13(10) . . ?
C7 C8 H8 125.4 . . ?
C9 C8 H8 125.4 . . ?
Fe1 C8 H8 127.5 . . ?
C8 C9 C10 106.53(15) . . ?
C8 C9 S2 124.52(13) . . ?
C10 C9 S2 128.77(13) . . ?
C8 C9 Fe1 70.74(10) . . ?
C10 C9 Fe1 67.70(9) . . ?
S2 C9 Fe1 122.68(9) . . ?
C6 C10 C9 107.86(15) . . ?
C6 C10 S1 125.74(14) . . ?
C9 C10 S1 126.26(13) . . ?
C6 C10 Fe1 70.25(10) . . ?
C9 C10 Fe1 69.52(9) . . ?
S1 C10 Fe1 122.48(10) . . ?
O12 S1 O11 120.93(10) . . ?
O12 S1 F13 104.78(9) . . ?
O11 S1 F13 105.23(10) . . ?
O12 S1 C10 112.30(9) . . ?
O11 S1 C10 110.96(9) . . ?
F13 S1 C10 99.92(8) . . ?
C9 S2 C14 103.43(8) . . ?
C19 C14 C15 120.13(17) . . ?
C19 C14 S2 115.99(14) . . ?
C15 C14 S2 123.83(14) . . ?
C14 C15 C16 119.17(18) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C17 C16 C15 120.64(19) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 119.90(19) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 120.4(2) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C14 C19 C18 119.80(19) . . ?
C14 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?

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
C5 C1 C2 C3 -0.1(2) . . . . ?
Fe1 C1 C2 C3 -59.03(14) . . . . ?
C5 C1 C2 Fe1 58.95(14) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
Fe1 C2 C3 C4 -59.33(14) . . . . ?
C1 C2 C3 Fe1 59.39(14) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
Fe1 C3 C4 C5 -59.85(14) . . . . ?
C2 C3 C4 Fe1 59.83(13) . . . . ?
C2 C1 C5 C4 0.1(2) . . . . ?
Fe1 C1 C5 C4 59.27(14) . . . . ?
C2 C1 C5 Fe1 -59.21(14) . . . . ?
C3 C4 C5 C1 0.0(2) . . . . ?
Fe1 C4 C5 C1 -59.88(14) . . . . ?
C3 C4 C5 Fe1 59.86(14) . . . . ?
C10 C6 C7 C8 -0.9(2) . . . . ?
Fe1 C6 C7 C8 57.07(13) . . . . ?
I1 C6 C7 C8 -177.92(12) . . . . ?
C10 C6 C7 Fe1 -57.98(12) . . . . ?
I1 C6 C7 Fe1 125.01(12) . . . . ?
C6 C7 C8 C9 0.7(2) . . . . ?
Fe1 C7 C8 C9 57.21(12) . . . . ?
C6 C7 C8 Fe1 -56.53(13) . . . . ?
C7 C8 C9 C10 -0.18(19) . . . . ?
Fe1 C8 C9 C10 58.46(11) . . . . ?
C7 C8 C9 S2 -175.64(13) . . . . ?
Fe1 C8 C9 S2 -117.00(13) . . . . ?
C7 C8 C9 Fe1 -58.64(13) . . . . ?
C7 C6 C10 C9 0.78(19) . . . . ?
Fe1 C6 C10 C9 -59.59(11) . . . . ?
I1 C6 C10 C9 177.35(13) . . . . ?
C7 C6 C10 S1 176.77(13) . . . . ?
Fe1 C6 C10 S1 116.40(14) . . . . ?
I1 C6 C10 S1 -6.7(3) . . . . ?
C7 C6 C10 Fe1 60.37(12) . . . . ?
I1 C6 C10 Fe1 -123.06(15) . . . . ?
C8 C9 C10 C6 -0.37(19) . . . . ?
S2 C9 C10 C6 174.83(13) . . . . ?
Fe1 C9 C10 C6 60.05(12) . . . . ?
C8 C9 C10 S1 -176.34(13) . . . . ?
S2 C9 C10 S1 -1.1(2) . . . . ?
Fe1 C9 C10 S1 -115.91(14) . . . . ?
C8 C9 C10 Fe1 -60.42(12) . . . . ?
S2 C9 C10 Fe1 114.78(15) . . . . ?
C6 C10 S1 O12 -153.13(16) . . . . ?
C9 C10 S1 O12 22.13(19) . . . . ?
Fe1 C10 S1 O12 -65.15(14) . . . . ?
C6 C10 S1 O11 -14.37(19) . . . . ?
C9 C10 S1 O11 160.90(16) . . . . ?
Fe1 C10 S1 O11 73.61(14) . . . . ?
C6 C10 S1 F13 96.28(16) . . . . ?
C9 C10 S1 F13 -88.46(16) . . . . ?
Fe1 C10 S1 F13 -175.75(10) . . . . ?
C8 C9 S2 C14 -78.61(16) . . . . ?
C10 C9 S2 C14 106.97(16) . . . . ?
Fe1 C9 S2 C14 -166.64(10) . . . . ?
C9 S2 C14 C19 158.12(14) . . . . ?
C9 S2 C14 C15 -24.57(17) . . . . ?
C19 C14 C15 C16 -0.4(3) . . . . ?
S2 C14 C15 C16 -177.58(14) . . . . ?
C14 C15 C16 C17 0.8(3) . . . . ?
C15 C16 C17 C18 -0.7(3) . . . . ?
C16 C17 C18 C19 0.1(3) . . . . ?
C15 C14 C19 C18 -0.2(3) . . . . ?
S2 C14 C19 C18 177.25(15) . . . . ?
C17 C18 C19 C14 0.3(3) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


####################################################################### 
# 
# 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_WE17461
_database_code_depnum_ccdc_archive 'CCDC 2189753'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;ISCR
France
;
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2022-09-25 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 22 novembre 2021                                         #
#------------------------------------------------------------------------------#


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H16 F2 Fe O2 S Si'
_chemical_formula_sum            'C13 H16 F2 Fe O2 S Si'
_chemical_formula_weight         358.26
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
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                   8.9485(5)
_cell_length_b                   11.4607(6)
_cell_length_c                   14.4020(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.087(2)
_cell_angle_gamma                90
_cell_volume                     1462.32(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9969
_cell_measurement_theta_min      2.8704
_cell_measurement_theta_max      27.4189
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      -0.1125646
_diffrn_orient_matrix_UB_21      -0.0072342
_diffrn_orient_matrix_UB_31      0.0042250
_diffrn_orient_matrix_UB_12      -0.0051644
_diffrn_orient_matrix_UB_22      0.0863735
_diffrn_orient_matrix_UB_32      0.0102982
_diffrn_orient_matrix_UB_13      -0.0128624
_diffrn_orient_matrix_UB_23      0.0073925
_diffrn_orient_matrix_UB_33      -0.0684535


#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.140
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             736
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.724
_exptl_absorpt_correction_T_max  0.837

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

# Software                   : BIS V6.2.15/2021-03-15 && APEX4 2021.10-0       #
# Number of scans            :        5                                        #
# Total number of frames     :      378                                        #
# Total length of scans      :   378.00 (deg.)                                 #
# Rotation speed             :     5.00 sec./deg.                              #
# Total exposition time      :         31.5 min.                               #
#                                                                              #
#    Scan  Time(s) Width DX(mm) Frames Range 2Theta  Omega    Phi    Chi  T(K) #
#..............................................................................#
#                                                                              #
#  1 Fast     1.0  1.00    34.0   180  180.0    0.0  360.0    0.0   54.7 150.0 #
#  2 Fast@    1.0  1.00    34.0   180  180.0    0.0  360.0  180.0   54.7 150.0 #
#  3 Omega    5.0  1.00    34.0    97   97.0    0.1    2.7    0.0  315.5 150.0 #
#  4 Omega    5.0  1.00    34.0    97   97.0    0.1    2.7  144.0  315.5 150.0 #
#  5 Phi      5.0  1.00    34.0   184  184.0    0.1    2.4  188.0  315.5 150.0 #
#                                                                              #
#  @: attenuated beam                                                          #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.00
_diffrn_source_voltage           50.00
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0301
_diffrn_reflns_av_r_equivalents  0.0523
_diffrn_reflns_number            19150
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.530
_diffrn_reflns_theta_max         27.459
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.960
_reflns_number_total             3215
_reflns_number_gt                3024
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2021)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0692P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018_3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0188(17)
_refine_ls_number_reflns         3215
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0990
_refine_ls_wR_factor_gt          0.0962
_refine_ls_goodness_of_fit_ref   1.204
_refine_ls_restrained_S_all      1.204
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.079

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'
F F 0.0171 0.0103 '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'
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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.17597(2) 0.27221(2) 0.40272(2) 0.01468(12) Uani 1 1 d . . . . .
C1 C 0.13499(17) 0.43194(13) 0.34012(11) 0.0259(3) Uani 1 1 d . . . . .
H1 H 0.168002 0.457173 0.283543 0.031 Uiso 1 1 calc R U . . .
C2 C 0.21588(17) 0.44492(13) 0.43240(12) 0.0267(3) Uani 1 1 d . . . . .
H2 H 0.312270 0.480038 0.448170 0.032 Uiso 1 1 calc R U . . .
C3 C 0.12618(17) 0.39586(13) 0.49618(10) 0.0248(3) Uani 1 1 d . . . . .
H3 H 0.152133 0.392486 0.562394 0.030 Uiso 1 1 calc R U . . .
C4 C -0.00897(15) 0.35269(12) 0.44417(10) 0.0226(3) Uani 1 1 d . . . . .
H4 H -0.089231 0.315517 0.469383 0.027 Uiso 1 1 calc R U . . .
C5 C -0.00300(16) 0.37487(13) 0.34784(10) 0.0237(3) Uani 1 1 d . . . . .
H5 H -0.078595 0.354860 0.297242 0.028 Uiso 1 1 calc R U . . .
C6 C 0.20571(16) 0.11215(12) 0.46071(10) 0.0232(3) Uani 1 1 d . . . . .
C7 C 0.12726(15) 0.09966(12) 0.37008(10) 0.0232(3) Uani 1 1 d . . . . .
H7 H 0.030700 0.065146 0.353351 0.028 Uiso 1 1 calc R U . . .
C8 C 0.22067(14) 0.14890(12) 0.30781(9) 0.0188(3) Uani 1 1 d . . . . .
H8 H 0.194897 0.152054 0.241580 0.023 Uiso 1 1 calc R U . . .
C9 C 0.35872(14) 0.19307(12) 0.35831(9) 0.0164(3) Uani 1 1 d . . . . .
C10 C 0.34686(15) 0.16906(12) 0.45612(9) 0.0190(3) Uani 1 1 d . . . . .
F11 F 0.16018(12) 0.07078(9) 0.53935(7) 0.0389(3) Uani 1 1 d . . . . .
Si1 Si 0.51327(4) 0.25623(4) 0.29711(3) 0.01958(13) Uani 1 1 d . . . . .
C12 C 0.4340(2) 0.26171(16) 0.17051(12) 0.0333(4) Uani 1 1 d . . . . .
H12A H 0.342439 0.309735 0.162344 0.050 Uiso 1 1 calc R U . . .
H12B H 0.409071 0.182503 0.147768 0.050 Uiso 1 1 calc R U . . .
H12C H 0.508639 0.295779 0.134786 0.050 Uiso 1 1 calc R U . . .
C13 C 0.67485(17) 0.15189(15) 0.31565(14) 0.0361(4) Uani 1 1 d . . . . .
H13A H 0.752982 0.176777 0.278571 0.054 Uiso 1 1 calc R U . . .
H13B H 0.639549 0.073622 0.295856 0.054 Uiso 1 1 calc R U . . .
H13C H 0.716862 0.150491 0.382261 0.054 Uiso 1 1 calc R U . . .
C14 C 0.57308(17) 0.40732(13) 0.33290(11) 0.0280(3) Uani 1 1 d . . . . .
H14A H 0.645042 0.435809 0.292751 0.042 Uiso 1 1 calc R U . . .
H14B H 0.621111 0.407059 0.398396 0.042 Uiso 1 1 calc R U . . .
H14C H 0.484537 0.458555 0.326377 0.042 Uiso 1 1 calc R U . . .
S1 S 0.47104(5) 0.20792(3) 0.55298(3) 0.02923(14) Uani 1 1 d . . . . .
F16 F 0.55986(13) 0.09123(10) 0.57376(8) 0.0495(3) Uani 1 1 d . . . . .
O17 O 0.57741(18) 0.28920(13) 0.53047(10) 0.0509(4) Uani 1 1 d . . . . .
O18 O 0.3967(2) 0.22536(16) 0.63203(10) 0.0600(5) Uani 1 1 d . . . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_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 C10 1.9991(13) . ?
Fe1 C6 2.0176(14) . ?
Fe1 C8 2.0443(13) . ?
Fe1 C2 2.0458(14) . ?
Fe1 C3 2.0463(14) . ?
Fe1 C9 2.0495(12) . ?
Fe1 C1 2.0508(15) . ?
Fe1 C5 2.0537(14) . ?
Fe1 C4 2.0552(13) . ?
Fe1 C7 2.0649(14) . ?
C1 C5 1.415(2) . ?
C1 C2 1.429(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.418(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.419(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.419(2) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 F11 1.3428(16) . ?
C6 C7 1.400(2) . ?
C6 C10 1.4313(19) . ?
C7 C8 1.4256(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.4347(18) . ?
C8 H8 0.9500 . ?
C9 C10 1.4537(17) . ?
C9 Si1 1.8859(13) . ?
C10 S1 1.7155(14) . ?
Si1 C12 1.8623(19) . ?
Si1 C14 1.8636(15) . ?
Si1 C13 1.8663(16) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
S1 O17 1.4020(16) . ?
S1 O18 1.4111(16) . ?
S1 F16 1.5630(11) . ?

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 Fe1 C6 41.75(6) . . ?
C10 Fe1 C8 68.74(5) . . ?
C6 Fe1 C8 67.76(6) . . ?
C10 Fe1 C2 112.96(6) . . ?
C6 Fe1 C2 141.65(7) . . ?
C8 Fe1 C2 139.79(6) . . ?
C10 Fe1 C3 112.46(6) . . ?
C6 Fe1 C3 112.68(6) . . ?
C8 Fe1 C3 178.67(5) . . ?
C2 Fe1 C3 40.56(6) . . ?
C10 Fe1 C9 42.06(5) . . ?
C6 Fe1 C9 70.26(5) . . ?
C8 Fe1 C9 41.03(5) . . ?
C2 Fe1 C9 111.71(6) . . ?
C3 Fe1 C9 140.26(6) . . ?
C10 Fe1 C1 140.97(6) . . ?
C6 Fe1 C1 176.97(6) . . ?
C8 Fe1 C1 111.27(6) . . ?
C2 Fe1 C1 40.83(6) . . ?
C3 Fe1 C1 68.22(6) . . ?
C9 Fe1 C1 111.04(6) . . ?
C10 Fe1 C5 178.65(6) . . ?
C6 Fe1 C5 136.93(6) . . ?
C8 Fe1 C5 110.73(6) . . ?
C2 Fe1 C5 68.28(6) . . ?
C3 Fe1 C5 68.05(6) . . ?
C9 Fe1 C5 138.31(5) . . ?
C1 Fe1 C5 40.35(6) . . ?
C10 Fe1 C4 139.23(5) . . ?
C6 Fe1 C4 110.64(6) . . ?
C8 Fe1 C4 138.22(5) . . ?
C2 Fe1 C4 68.23(6) . . ?
C3 Fe1 C4 40.48(6) . . ?
C9 Fe1 C4 178.70(5) . . ?
C1 Fe1 C4 68.01(6) . . ?
C5 Fe1 C4 40.40(6) . . ?
C10 Fe1 C7 69.32(6) . . ?
C6 Fe1 C7 40.08(6) . . ?
C8 Fe1 C7 40.60(5) . . ?
C2 Fe1 C7 177.72(6) . . ?
C3 Fe1 C7 138.98(6) . . ?
C9 Fe1 C7 69.96(5) . . ?
C1 Fe1 C7 137.38(6) . . ?
C5 Fe1 C7 109.44(6) . . ?
C4 Fe1 C7 110.07(6) . . ?
C5 C1 C2 107.96(13) . . ?
C5 C1 Fe1 69.94(8) . . ?
C2 C1 Fe1 69.40(8) . . ?
C5 C1 H1 126.0 . . ?
C2 C1 H1 126.0 . . ?
Fe1 C1 H1 126.2 . . ?
C3 C2 C1 107.60(13) . . ?
C3 C2 Fe1 69.74(8) . . ?
C1 C2 Fe1 69.77(8) . . ?
C3 C2 H2 126.2 . . ?
C1 C2 H2 126.2 . . ?
Fe1 C2 H2 125.9 . . ?
C2 C3 C4 108.32(13) . . ?
C2 C3 Fe1 69.70(8) . . ?
C4 C3 Fe1 70.10(8) . . ?
C2 C3 H3 125.8 . . ?
C4 C3 H3 125.8 . . ?
Fe1 C3 H3 125.9 . . ?
C5 C4 C3 107.89(12) . . ?
C5 C4 Fe1 69.74(8) . . ?
C3 C4 Fe1 69.42(7) . . ?
C5 C4 H4 126.1 . . ?
C3 C4 H4 126.1 . . ?
Fe1 C4 H4 126.3 . . ?
C1 C5 C4 108.23(13) . . ?
C1 C5 Fe1 69.72(8) . . ?
C4 C5 Fe1 69.86(8) . . ?
C1 C5 H5 125.9 . . ?
C4 C5 H5 125.9 . . ?
Fe1 C5 H5 126.1 . . ?
F11 C6 C7 125.34(14) . . ?
F11 C6 C10 125.05(13) . . ?
C7 C6 C10 109.49(12) . . ?
F11 C6 Fe1 129.21(10) . . ?
C7 C6 Fe1 71.78(8) . . ?
C10 C6 Fe1 68.43(8) . . ?
C6 C7 C8 106.53(12) . . ?
C6 C7 Fe1 68.14(8) . . ?
C8 C7 Fe1 68.93(8) . . ?
C6 C7 H7 126.7 . . ?
C8 C7 H7 126.7 . . ?
Fe1 C7 H7 127.7 . . ?
C7 C8 C9 111.10(12) . . ?
C7 C8 Fe1 70.48(8) . . ?
C9 C8 Fe1 69.68(7) . . ?
C7 C8 H8 124.4 . . ?
C9 C8 H8 124.4 . . ?
Fe1 C8 H8 127.0 . . ?
C8 C9 C10 104.44(10) . . ?
C8 C9 Si1 122.29(9) . . ?
C10 C9 Si1 133.14(10) . . ?
C8 C9 Fe1 69.29(7) . . ?
C10 C9 Fe1 67.11(7) . . ?
Si1 C9 Fe1 130.22(7) . . ?
C6 C10 C9 108.43(11) . . ?
C6 C10 S1 123.75(10) . . ?
C9 C10 S1 127.70(10) . . ?
C6 C10 Fe1 69.82(8) . . ?
C9 C10 Fe1 70.82(7) . . ?
S1 C10 Fe1 122.16(7) . . ?
C12 Si1 C14 107.13(8) . . ?
C12 Si1 C13 110.03(9) . . ?
C14 Si1 C13 111.67(7) . . ?
C12 Si1 C9 105.49(7) . . ?
C14 Si1 C9 115.36(6) . . ?
C13 Si1 C9 106.95(7) . . ?
Si1 C12 H12A 109.5 . . ?
Si1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
Si1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
Si1 C13 H13A 109.5 . . ?
Si1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
Si1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
Si1 C14 H14A 109.5 . . ?
Si1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
Si1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O17 S1 O18 120.31(11) . . ?
O17 S1 F16 105.62(9) . . ?
O18 S1 F16 104.55(8) . . ?
O17 S1 C10 111.57(8) . . ?
O18 S1 C10 111.59(9) . . ?
F16 S1 C10 100.80(6) . . ?

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
C5 C1 C2 C3 -0.21(16) . . . . ?
Fe1 C1 C2 C3 -59.73(10) . . . . ?
C5 C1 C2 Fe1 59.53(10) . . . . ?
C1 C2 C3 C4 0.07(16) . . . . ?
Fe1 C2 C3 C4 -59.68(10) . . . . ?
C1 C2 C3 Fe1 59.76(10) . . . . ?
C2 C3 C4 C5 0.08(16) . . . . ?
Fe1 C3 C4 C5 -59.35(9) . . . . ?
C2 C3 C4 Fe1 59.43(10) . . . . ?
C2 C1 C5 C4 0.26(15) . . . . ?
Fe1 C1 C5 C4 59.45(9) . . . . ?
C2 C1 C5 Fe1 -59.19(10) . . . . ?
C3 C4 C5 C1 -0.21(15) . . . . ?
Fe1 C4 C5 C1 -59.36(10) . . . . ?
C3 C4 C5 Fe1 59.15(9) . . . . ?
F11 C6 C7 C8 -175.93(13) . . . . ?
C10 C6 C7 C8 0.26(15) . . . . ?
Fe1 C6 C7 C8 58.45(9) . . . . ?
F11 C6 C7 Fe1 125.62(14) . . . . ?
C10 C6 C7 Fe1 -58.20(9) . . . . ?
C6 C7 C8 C9 -0.08(15) . . . . ?
Fe1 C7 C8 C9 57.87(10) . . . . ?
C6 C7 C8 Fe1 -57.95(9) . . . . ?
C7 C8 C9 C10 -0.12(15) . . . . ?
Fe1 C8 C9 C10 58.22(8) . . . . ?
C7 C8 C9 Si1 176.37(10) . . . . ?
Fe1 C8 C9 Si1 -125.30(10) . . . . ?
C7 C8 C9 Fe1 -58.34(10) . . . . ?
F11 C6 C10 C9 175.86(13) . . . . ?
C7 C6 C10 C9 -0.34(15) . . . . ?
Fe1 C6 C10 C9 -60.57(9) . . . . ?
F11 C6 C10 S1 -7.7(2) . . . . ?
C7 C6 C10 S1 176.10(10) . . . . ?
Fe1 C6 C10 S1 115.88(11) . . . . ?
F11 C6 C10 Fe1 -123.57(14) . . . . ?
C7 C6 C10 Fe1 60.23(10) . . . . ?
C8 C9 C10 C6 0.27(14) . . . . ?
Si1 C9 C10 C6 -175.65(11) . . . . ?
Fe1 C9 C10 C6 59.94(9) . . . . ?
C8 C9 C10 S1 -175.99(10) . . . . ?
Si1 C9 C10 S1 8.1(2) . . . . ?
Fe1 C9 C10 S1 -116.32(12) . . . . ?
C8 C9 C10 Fe1 -59.66(9) . . . . ?
Si1 C9 C10 Fe1 124.41(13) . . . . ?
C8 C9 Si1 C12 6.48(13) . . . . ?
C10 C9 Si1 C12 -178.19(14) . . . . ?
Fe1 C9 Si1 C12 -82.76(10) . . . . ?
C8 C9 Si1 C14 124.48(12) . . . . ?
C10 C9 Si1 C14 -60.18(15) . . . . ?
Fe1 C9 Si1 C14 35.25(11) . . . . ?
C8 C9 Si1 C13 -110.65(12) . . . . ?
C10 C9 Si1 C13 64.68(15) . . . . ?
Fe1 C9 Si1 C13 160.11(9) . . . . ?
C6 C10 S1 O17 -163.51(13) . . . . ?
C9 C10 S1 O17 12.22(16) . . . . ?
Fe1 C10 S1 O17 -77.53(11) . . . . ?
C6 C10 S1 O18 -25.77(15) . . . . ?
C9 C10 S1 O18 149.96(13) . . . . ?
Fe1 C10 S1 O18 60.22(12) . . . . ?
C6 C10 S1 F16 84.75(12) . . . . ?
C9 C10 S1 F16 -99.51(13) . . . . ?
Fe1 C10 S1 F16 170.74(8) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


####################################################################### 
# 
# 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_WE17211
_database_code_depnum_ccdc_archive 'CCDC 2189757'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;ISCR
France
;
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2022-09-25 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 28 octobre 2021                                          #
#------------------------------------------------------------------------------#


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H12 F Fe I O2 S2'
_chemical_formula_sum            'C16 H12 F Fe I O2 S2'
_chemical_formula_weight         502.13
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.2866(6)
_cell_length_b                   18.0595(16)
_cell_length_c                   12.8343(13)
_cell_angle_alpha                90
_cell_angle_beta                 99.140(3)
_cell_angle_gamma                90
_cell_volume                     1667.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9880
_cell_measurement_theta_min      2.7699
_cell_measurement_theta_max      27.4828
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      0.0362048
_diffrn_orient_matrix_UB_21      0.1085798
_diffrn_orient_matrix_UB_31      -0.0788776
_diffrn_orient_matrix_UB_12      -0.0013847
_diffrn_orient_matrix_UB_22      0.0328356
_diffrn_orient_matrix_UB_32      0.0445647
_diffrn_orient_matrix_UB_13      0.0784667
_diffrn_orient_matrix_UB_23      -0.0054354
_diffrn_orient_matrix_UB_33      0.0064429


#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.170
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.000
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             976
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.021
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.445
_exptl_absorpt_correction_T_max  0.598

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

# Software                   : BIS V6.2.15/2021-03-15 && APEX3 2016.9-0        #
# Number of scans            :        2                                        #
# Total number of frames     :      248                                        #
# Total length of scans      :   248.00 (deg.)                                 #
# Rotation speed             :     5.00 sec./deg.                              #
# Total exposition time      :         20.7 min.                               #
#                                                                              #
#    Scan  Time(s) Width DX(mm) Frames Range 2Theta  Omega    Phi    Chi  T(K) #
#..............................................................................#
#                                                                              #
#  1 Phi      5.0  1.00    34.0   248  248.0    1.9  272.7  244.0   23.0 150.0 #
#  2 Fast     1.0  1.00    34.0   180  180.0    0.0  360.0    0.0   54.7 150.0 #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.00
_diffrn_source_voltage           50.00
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0250
_diffrn_reflns_av_r_equivalents  0.0291
_diffrn_reflns_number            15085
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.770
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_reflns_number_total             3807
_reflns_number_gt                3643
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2021)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0202P)²+1.7247P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         3807
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0223
_refine_ls_R_factor_gt           0.0209
_refine_ls_wR_factor_ref         0.0525
_refine_ls_wR_factor_gt          0.0518
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.742
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.075

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'
F F 0.0171 0.0103 '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'
I I -0.4742 1.8119 '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'

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
C1 C 0.1269(3) 0.56861(13) 0.89131(18) 0.0238(4) Uani 1 1 d . . . . .
H1 H 0.169857 0.580889 0.963010 0.029 Uiso 1 1 calc R U . . .
C2 C 0.1143(3) 0.61768(13) 0.80396(19) 0.0251(5) Uani 1 1 d . . . . .
H2 H 0.148830 0.668455 0.806903 0.030 Uiso 1 1 calc R U . . .
C3 C 0.0413(3) 0.57762(13) 0.71154(19) 0.0266(5) Uani 1 1 d . . . . .
H3 H 0.017286 0.597053 0.641923 0.032 Uiso 1 1 calc R U . . .
C4 C 0.0104(3) 0.50375(13) 0.74098(19) 0.0260(5) Uani 1 1 d . . . . .
H4 H -0.037517 0.464924 0.694557 0.031 Uiso 1 1 calc R U . . .
C5 C 0.0636(3) 0.49771(13) 0.85224(18) 0.0245(4) Uani 1 1 d . . . . .
H5 H 0.057851 0.454181 0.893164 0.029 Uiso 1 1 calc R U . . .
C6 C 0.5472(3) 0.57547(11) 0.78310(16) 0.0176(4) Uani 1 1 d . . . . .
C7 C 0.4734(3) 0.54650(12) 0.68272(16) 0.0195(4) Uani 1 1 d . . . . .
H7 H 0.453609 0.572765 0.617772 0.023 Uiso 1 1 calc R U . . .
C8 C 0.4341(3) 0.46982(11) 0.69804(15) 0.0175(4) Uani 1 1 d . . . . .
C9 C 0.4823(3) 0.45178(11) 0.80924(15) 0.0165(4) Uani 1 1 d . . . . .
C10 C 0.5534(3) 0.51886(11) 0.86042(16) 0.0168(4) Uani 1 1 d . . . . .
H10 H 0.597189 0.524469 0.933753 0.020 Uiso 1 1 calc R U . . .
O11 O 0.2294(3) 0.35489(10) 0.62973(14) 0.0357(4) Uani 1 1 d . . . . .
O12 O 0.2656(3) 0.45710(11) 0.50710(13) 0.0359(4) Uani 1 1 d . . . . .
F13 F 0.5139(2) 0.37513(8) 0.56758(12) 0.0367(3) Uani 1 1 d . . . . .
C14 C 0.6656(3) 0.32364(11) 0.88335(17) 0.0183(4) Uani 1 1 d . . . . .
C15 C 0.7903(3) 0.33700(12) 0.81426(18) 0.0231(4) Uani 1 1 d . . . . .
H15 H 0.759172 0.370605 0.757247 0.028 Uiso 1 1 calc R U . . .
C16 C 0.9619(3) 0.30080(14) 0.8290(2) 0.0277(5) Uani 1 1 d . . . . .
H16 H 1.048440 0.310365 0.782545 0.033 Uiso 1 1 calc R U . . .
C17 C 1.0060(3) 0.25104(13) 0.9111(2) 0.0312(5) Uani 1 1 d . . . . .
H17 H 1.123718 0.227223 0.921872 0.037 Uiso 1 1 calc R U . . .
C18 C 0.8789(4) 0.23601(14) 0.9773(2) 0.0324(5) Uani 1 1 d . . . . .
H18 H 0.908187 0.200782 1.032420 0.039 Uiso 1 1 calc R U . . .
C19 C 0.7084(3) 0.27205(13) 0.96394(18) 0.0259(5) Uani 1 1 d . . . . .
H19 H 0.621282 0.261493 1.009708 0.031 Uiso 1 1 calc R U . . .
Fe1 Fe 0.28580(4) 0.53121(2) 0.78299(2) 0.01457(7) Uani 1 1 d . . . . .
I1 I 0.63197(2) 0.68482(2) 0.80985(2) 0.02332(6) Uani 1 1 d . . . . .
S1 S 0.33506(8) 0.41369(3) 0.59633(4) 0.02371(12) Uani 1 1 d . . . . .
S2 S 0.44643(7) 0.36837(3) 0.87334(4) 0.01930(10) Uani 1 1 d . . . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_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
C1 C2 1.420(3) . ?
C1 C5 1.425(3) . ?
C1 Fe1 2.059(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.419(3) . ?
C2 Fe1 2.044(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.414(3) . ?
C3 Fe1 2.049(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.423(3) . ?
C4 Fe1 2.054(2) . ?
C4 H4 0.9500 . ?
C5 Fe1 2.058(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.415(3) . ?
C6 C10 1.421(3) . ?
C6 Fe1 2.0655(19) . ?
C6 I1 2.081(2) . ?
C7 C8 1.434(3) . ?
C7 Fe1 2.039(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.452(3) . ?
C8 S1 1.718(2) . ?
C8 Fe1 1.990(2) . ?
C9 C10 1.435(3) . ?
C9 S2 1.756(2) . ?
C9 Fe1 2.017(2) . ?
C10 Fe1 2.0549(19) . ?
C10 H10 0.9500 . ?
O11 S1 1.4173(19) . ?
O12 S1 1.4135(18) . ?
F13 S1 1.5724(15) . ?
C14 C15 1.388(3) . ?
C14 C19 1.390(3) . ?
C14 S2 1.776(2) . ?
C15 C16 1.397(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.383(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.380(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.389(3) . ?
C18 H18 0.9500 . ?
C19 H19 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
C2 C1 C5 107.8(2) . . ?
C2 C1 Fe1 69.17(12) . . ?
C5 C1 Fe1 69.70(12) . . ?
C2 C1 H1 126.1 . . ?
C5 C1 H1 126.1 . . ?
Fe1 C1 H1 126.6 . . ?
C3 C2 C1 108.1(2) . . ?
C3 C2 Fe1 69.90(12) . . ?
C1 C2 Fe1 70.32(12) . . ?
C3 C2 H2 126.0 . . ?
C1 C2 H2 126.0 . . ?
Fe1 C2 H2 125.4 . . ?
C4 C3 C2 108.2(2) . . ?
C4 C3 Fe1 70.04(12) . . ?
C2 C3 Fe1 69.54(12) . . ?
C4 C3 H3 125.9 . . ?
C2 C3 H3 125.9 . . ?
Fe1 C3 H3 126.1 . . ?
C3 C4 C5 108.1(2) . . ?
C3 C4 Fe1 69.64(12) . . ?
C5 C4 Fe1 69.90(12) . . ?
C3 C4 H4 125.9 . . ?
C5 C4 H4 125.9 . . ?
Fe1 C4 H4 126.1 . . ?
C1 C5 C4 107.8(2) . . ?
C1 C5 Fe1 69.80(12) . . ?
C4 C5 Fe1 69.61(12) . . ?
C1 C5 H5 126.1 . . ?
C4 C5 H5 126.1 . . ?
Fe1 C5 H5 126.1 . . ?
C7 C6 C10 109.58(18) . . ?
C7 C6 Fe1 68.84(11) . . ?
C10 C6 Fe1 69.43(11) . . ?
C7 C6 I1 124.12(15) . . ?
C10 C6 I1 126.30(15) . . ?
Fe1 C6 I1 128.08(10) . . ?
C6 C7 C8 106.71(18) . . ?
C6 C7 Fe1 70.83(11) . . ?
C8 C7 Fe1 67.32(11) . . ?
C6 C7 H7 126.6 . . ?
C8 C7 H7 126.6 . . ?
Fe1 C7 H7 126.7 . . ?
C7 C8 C9 109.22(17) . . ?
C7 C8 S1 122.31(15) . . ?
C9 C8 S1 128.41(16) . . ?
C7 C8 Fe1 71.01(11) . . ?
C9 C8 Fe1 69.75(11) . . ?
S1 C8 Fe1 123.08(11) . . ?
C10 C9 C8 105.90(17) . . ?
C10 C9 S2 125.42(15) . . ?
C8 C9 S2 128.50(15) . . ?
C10 C9 Fe1 70.80(11) . . ?
C8 C9 Fe1 67.77(11) . . ?
S2 C9 Fe1 122.28(10) . . ?
C6 C10 C9 108.59(18) . . ?
C6 C10 Fe1 70.23(11) . . ?
C9 C10 Fe1 67.95(11) . . ?
C6 C10 H10 125.7 . . ?
C9 C10 H10 125.7 . . ?
Fe1 C10 H10 127.7 . . ?
C15 C14 C19 120.0(2) . . ?
C15 C14 S2 123.17(16) . . ?
C19 C14 S2 116.82(17) . . ?
C14 C15 C16 119.7(2) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 120.1(2) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 120.0(2) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.4(2) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C14 119.8(2) . . ?
C18 C19 H19 120.1 . . ?
C14 C19 H19 120.1 . . ?
C8 Fe1 C9 42.48(8) . . ?
C8 Fe1 C7 41.67(8) . . ?
C9 Fe1 C7 70.89(8) . . ?
C8 Fe1 C2 153.40(9) . . ?
C9 Fe1 C2 162.52(9) . . ?
C7 Fe1 C2 117.68(9) . . ?
C8 Fe1 C3 119.47(9) . . ?
C9 Fe1 C3 155.42(9) . . ?
C7 Fe1 C3 106.53(9) . . ?
C2 Fe1 C3 40.56(9) . . ?
C8 Fe1 C4 108.34(9) . . ?
C9 Fe1 C4 120.67(9) . . ?
C7 Fe1 C4 126.28(9) . . ?
C2 Fe1 C4 68.09(9) . . ?
C3 Fe1 C4 40.32(10) . . ?
C8 Fe1 C10 69.42(8) . . ?
C9 Fe1 C10 41.26(8) . . ?
C7 Fe1 C10 68.93(8) . . ?
C2 Fe1 C10 124.89(9) . . ?
C3 Fe1 C10 162.08(9) . . ?
C4 Fe1 C10 155.92(9) . . ?
C8 Fe1 C5 127.29(9) . . ?
C9 Fe1 C5 107.77(9) . . ?
C7 Fe1 C5 164.69(9) . . ?
C2 Fe1 C5 68.18(9) . . ?
C3 Fe1 C5 68.01(10) . . ?
C4 Fe1 C5 40.50(9) . . ?
C10 Fe1 C5 120.69(9) . . ?
C8 Fe1 C1 164.82(9) . . ?
C9 Fe1 C1 125.51(9) . . ?
C7 Fe1 C1 152.45(9) . . ?
C2 Fe1 C1 40.50(9) . . ?
C3 Fe1 C1 68.02(9) . . ?
C4 Fe1 C1 68.02(9) . . ?
C10 Fe1 C1 107.52(8) . . ?
C5 Fe1 C1 40.49(9) . . ?
C8 Fe1 C6 68.59(8) . . ?
C9 Fe1 C6 69.21(8) . . ?
C7 Fe1 C6 40.33(8) . . ?
C2 Fe1 C6 106.69(9) . . ?
C3 Fe1 C6 125.32(9) . . ?
C4 Fe1 C6 162.92(9) . . ?
C10 Fe1 C6 40.33(8) . . ?
C5 Fe1 C6 154.46(9) . . ?
C1 Fe1 C6 119.34(9) . . ?
O12 S1 O11 121.26(12) . . ?
O12 S1 F13 105.00(10) . . ?
O11 S1 F13 104.45(11) . . ?
O12 S1 C8 109.96(11) . . ?
O11 S1 C8 113.27(10) . . ?
F13 S1 C8 100.12(9) . . ?
C9 S2 C14 103.01(9) . . ?

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
C5 C1 C2 C3 0.8(2) . . . . ?
Fe1 C1 C2 C3 59.96(15) . . . . ?
C5 C1 C2 Fe1 -59.19(14) . . . . ?
C1 C2 C3 C4 -0.6(2) . . . . ?
Fe1 C2 C3 C4 59.59(15) . . . . ?
C1 C2 C3 Fe1 -60.23(15) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
Fe1 C3 C4 C5 59.53(15) . . . . ?
C2 C3 C4 Fe1 -59.28(15) . . . . ?
C2 C1 C5 C4 -0.6(2) . . . . ?
Fe1 C1 C5 C4 -59.48(14) . . . . ?
C2 C1 C5 Fe1 58.86(14) . . . . ?
C3 C4 C5 C1 0.2(2) . . . . ?
Fe1 C4 C5 C1 59.60(14) . . . . ?
C3 C4 C5 Fe1 -59.37(15) . . . . ?
C10 C6 C7 C8 -0.5(2) . . . . ?
Fe1 C6 C7 C8 -57.96(14) . . . . ?
I1 C6 C7 C8 179.59(13) . . . . ?
C10 C6 C7 Fe1 57.48(14) . . . . ?
I1 C6 C7 Fe1 -122.45(14) . . . . ?
C6 C7 C8 C9 0.7(2) . . . . ?
Fe1 C7 C8 C9 -59.49(14) . . . . ?
C6 C7 C8 S1 177.93(15) . . . . ?
Fe1 C7 C8 S1 117.73(16) . . . . ?
C6 C7 C8 Fe1 60.20(14) . . . . ?
C7 C8 C9 C10 -0.7(2) . . . . ?
S1 C8 C9 C10 -177.67(15) . . . . ?
Fe1 C8 C9 C10 -60.93(13) . . . . ?
C7 C8 C9 S2 174.61(15) . . . . ?
S1 C8 C9 S2 -2.4(3) . . . . ?
Fe1 C8 C9 S2 114.34(17) . . . . ?
C7 C8 C9 Fe1 60.27(14) . . . . ?
S1 C8 C9 Fe1 -116.73(18) . . . . ?
C7 C6 C10 C9 0.1(2) . . . . ?
Fe1 C6 C10 C9 57.20(13) . . . . ?
I1 C6 C10 C9 180.00(13) . . . . ?
C7 C6 C10 Fe1 -57.13(14) . . . . ?
I1 C6 C10 Fe1 122.80(15) . . . . ?
C8 C9 C10 C6 0.4(2) . . . . ?
S2 C9 C10 C6 -175.09(14) . . . . ?
Fe1 C9 C10 C6 -58.59(14) . . . . ?
C8 C9 C10 Fe1 58.96(13) . . . . ?
S2 C9 C10 Fe1 -116.50(16) . . . . ?
C19 C14 C15 C16 -2.8(3) . . . . ?
S2 C14 C15 C16 178.51(17) . . . . ?
C14 C15 C16 C17 1.0(3) . . . . ?
C15 C16 C17 C18 1.3(4) . . . . ?
C16 C17 C18 C19 -1.8(4) . . . . ?
C17 C18 C19 C14 0.0(4) . . . . ?
C15 C14 C19 C18 2.3(3) . . . . ?
S2 C14 C19 C18 -178.88(19) . . . . ?
C7 C8 S1 O12 -12.5(2) . . . . ?
C9 C8 S1 O12 164.15(19) . . . . ?
Fe1 C8 S1 O12 74.77(15) . . . . ?
C7 C8 S1 O11 -151.70(17) . . . . ?
C9 C8 S1 O11 24.9(2) . . . . ?
Fe1 C8 S1 O11 -64.43(16) . . . . ?
C7 C8 S1 F13 97.65(18) . . . . ?
C9 C8 S1 F13 -85.7(2) . . . . ?
Fe1 C8 S1 F13 -175.08(12) . . . . ?
C10 C9 S2 C14 -87.50(18) . . . . ?
C8 C9 S2 C14 98.09(19) . . . . ?
Fe1 C9 S2 C14 -175.88(11) . . . . ?
C15 C14 S2 C9 -26.0(2) . . . . ?
C19 C14 S2 C9 155.25(17) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


####################################################################### 
# 
# 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_WE15863
_database_code_depnum_ccdc_archive 'CCDC 2189768'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;ISCR
France
;
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2022-09-25 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 26 juillet 2021                                          #
#------------------------------------------------------------------------------#


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C17 H22 F Fe N O3 S Si'
_chemical_formula_sum            'C17 H22 F Fe N O3 S Si'
_chemical_formula_weight         423.35
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.8130(4)
_cell_length_b                   18.7277(9)
_cell_length_c                   29.0696(15)
_cell_angle_alpha                90
_cell_angle_beta                 94.188(2)
_cell_angle_gamma                90
_cell_volume                     3699.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7878
_cell_measurement_theta_min      2.3715
_cell_measurement_theta_max      26.8027
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      -0.0931681
_diffrn_orient_matrix_UB_21      0.1120697
_diffrn_orient_matrix_UB_31      -0.0204747
_diffrn_orient_matrix_UB_12      -0.0161521
_diffrn_orient_matrix_UB_22      -0.0041607
_diffrn_orient_matrix_UB_32      0.0507250
_diffrn_orient_matrix_UB_13      0.0229175
_diffrn_orient_matrix_UB_23      0.0240534
_diffrn_orient_matrix_UB_33      0.0092705


#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.160
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1760
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.019
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.720
_exptl_absorpt_correction_T_max  0.850

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

# Software                   : BIS 2014.5.0.0/23-May-2014 && APEX2_2014.11-0   #
# Number of scans            :        3                                        #
# Total number of frames     :      587                                        #
# Total length of scans      :   293.50 (deg.)                                 #
# Rotation speed             :    30.00 sec./deg.                              #
# Total exposition time      :      2 h  26.8 min.                             #
#                                                                              #
#    Scan  Time(s) Width DX(mm) Frames Range 2Theta  Omega    Phi    Chi  T(K) #
#..............................................................................#
#                                                                              #
#  1 Omega   15.0  0.50    35.0   211  105.5   16.0   14.5   54.4  308.2 150.0 #
#  2 Omega   15.0  0.50    35.0   186   93.0  344.0  341.8  153.7  335.0 150.0 #
#  3 Omega   15.0  0.50    35.0   190   95.0  344.0  252.5  114.6   26.9 150.0 #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'APEXII Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 CCD-LDI-APEX2
_diffrn_detector_area_resol_mean 10.4167
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_source_current           1.0
_diffrn_source_voltage           50.0
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0535
_diffrn_reflns_av_r_equivalents  0.0406
_diffrn_reflns_number            24818
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         0.702
_diffrn_reflns_theta_max         27.575
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.986
_reflns_number_total             8464
_reflns_number_gt                7123
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2020)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+25.9646P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         8464
_refine_ls_number_parameters     458
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0632
_refine_ls_wR_factor_ref         0.1285
_refine_ls_wR_factor_gt          0.1223
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_restrained_S_all      0.958
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.694
_refine_diff_density_min         -0.624
_refine_diff_density_rms         0.100

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.51504(9) 0.52441(3) 0.69048(2) 0.01707(13) Uani 1 1 d . . . . .
C1 C 0.7600(7) 0.4871(3) 0.72786(18) 0.0341(12) Uani 1 1 d . . . . .
H1 H 0.761209 0.451907 0.751389 0.041 Uiso 1 1 calc R U . . .
C2 C 0.7759(7) 0.4745(3) 0.67998(19) 0.0356(12) Uani 1 1 d . . . . .
H2 H 0.790523 0.429186 0.665913 0.043 Uiso 1 1 calc R U . . .
C3 C 0.7663(7) 0.5406(3) 0.65719(16) 0.0296(11) Uani 1 1 d . . . . .
H3 H 0.771246 0.547786 0.624951 0.036 Uiso 1 1 calc R U . . .
C4 C 0.7480(7) 0.5945(3) 0.69064(17) 0.0293(11) Uani 1 1 d . . . . .
H4 H 0.740856 0.644385 0.684861 0.035 Uiso 1 1 calc R U . . .
C5 C 0.7422(7) 0.5614(3) 0.73399(17) 0.0329(11) Uani 1 1 d . . . . .
H5 H 0.728651 0.585069 0.762480 0.039 Uiso 1 1 calc R U . . .
C6 C 0.2654(6) 0.5702(2) 0.65767(14) 0.0167(8) Uani 1 1 d . . . . .
H6 H 0.261379 0.609589 0.637023 0.020 Uiso 1 1 calc R U . . .
C7 C 0.2534(6) 0.5759(2) 0.70607(14) 0.0170(8) Uani 1 1 d . . . . .
C8 C 0.2707(6) 0.5061(2) 0.72546(14) 0.0181(8) Uani 1 1 d . . . . .
H8 H 0.271956 0.493794 0.757186 0.022 Uiso 1 1 calc R U . . .
C9 C 0.2856(6) 0.4583(2) 0.68744(14) 0.0175(8) Uani 1 1 d . . . . .
C10 C 0.2845(6) 0.4969(2) 0.64412(14) 0.0168(8) Uani 1 1 d . . . . .
N11 N 0.2328(6) 0.64026(19) 0.72954(12) 0.0200(8) Uani 1 1 d . . . . .
C12 C 0.2313(8) 0.7091(2) 0.70531(16) 0.0294(11) Uani 1 1 d . . . . .
H12A H 0.138851 0.708309 0.677410 0.035 Uiso 1 1 calc R U . . .
H12B H 0.364311 0.721770 0.696368 0.035 Uiso 1 1 calc R U . . .
C13 C 0.1620(9) 0.7609(3) 0.74144(17) 0.0369(13) Uani 1 1 d . . . . .
H13A H 0.224435 0.808317 0.738669 0.044 Uiso 1 1 calc R U . . .
H13B H 0.017251 0.766694 0.738119 0.044 Uiso 1 1 calc R U . . .
C14 C 0.2272(8) 0.7260(3) 0.78723(16) 0.0298(11) Uani 1 1 d . . . . .
H14A H 0.358478 0.743589 0.798932 0.036 Uiso 1 1 calc R U . . .
H14B H 0.131890 0.735785 0.810574 0.036 Uiso 1 1 calc R U . . .
C15 C 0.2341(7) 0.6472(2) 0.77640(15) 0.0245(10) Uani 1 1 d . . . . .
O16 O 0.2460(6) 0.59834(18) 0.80397(11) 0.0359(9) Uani 1 1 d . . . . .
S1 S 0.32034(18) 0.36826(6) 0.69468(4) 0.0234(2) Uani 1 1 d . . . . .
O17 O 0.3790(6) 0.35056(18) 0.74097(12) 0.0393(9) Uani 1 1 d . . . . .
O18 O 0.4160(5) 0.33736(17) 0.65779(11) 0.0296(8) Uani 1 1 d . . . . .
F19 F 0.1020(4) 0.34038(15) 0.68695(12) 0.0411(8) Uani 1 1 d . . . . .
Si1 Si 0.27086(18) 0.46626(7) 0.58223(4) 0.0204(2) Uani 1 1 d . . . . .
C20 C 0.0763(7) 0.3967(3) 0.57352(17) 0.0281(10) Uani 1 1 d . . . . .
H20A H 0.064372 0.382219 0.541052 0.042 Uiso 1 1 calc R U . . .
H20B H -0.049550 0.416177 0.582033 0.042 Uiso 1 1 calc R U . . .
H20C H 0.111838 0.355227 0.592906 0.042 Uiso 1 1 calc R U . . .
C21 C 0.5097(7) 0.4323(3) 0.56450(17) 0.0329(11) Uani 1 1 d . . . . .
H21A H 0.559554 0.395354 0.586195 0.049 Uiso 1 1 calc R U . . .
H21B H 0.604464 0.471659 0.564515 0.049 Uiso 1 1 calc R U . . .
H21C H 0.491216 0.411928 0.533435 0.049 Uiso 1 1 calc R U . . .
C22 C 0.1962(8) 0.5463(3) 0.54682(16) 0.0307(11) Uani 1 1 d . . . . .
H22A H 0.297968 0.583143 0.551132 0.046 Uiso 1 1 calc R U . . .
H22B H 0.071355 0.564874 0.556551 0.046 Uiso 1 1 calc R U . . .
H22C H 0.180192 0.532777 0.514188 0.046 Uiso 1 1 calc R U . . .
Fe2 Fe 0.54519(9) 0.18333(3) 0.49636(2) 0.01889(14) Uani 1 1 d . . . . .
C51 C 0.8021(7) 0.1282(3) 0.5074(2) 0.0361(13) Uani 1 1 d . . . . .
H51 H 0.814977 0.077827 0.504945 0.043 Uiso 1 1 calc R U . . .
C52 C 0.8192(7) 0.1774(4) 0.4715(2) 0.0473(16) Uani 1 1 d . . . . .
H52 H 0.848319 0.166676 0.440833 0.057 Uiso 1 1 calc R U . . .
C53 C 0.7851(7) 0.2456(3) 0.4895(2) 0.0472(17) Uani 1 1 d . . . . .
H53 H 0.784151 0.289170 0.472774 0.057 Uiso 1 1 calc R U . . .
C54 C 0.7524(8) 0.2381(3) 0.5367(2) 0.0406(14) Uani 1 1 d . . . . .
H54 H 0.727508 0.275588 0.557491 0.049 Uiso 1 1 calc R U . . .
C55 C 0.7635(7) 0.1652(3) 0.54695(18) 0.0332(12) Uani 1 1 d . . . . .
H55 H 0.747174 0.144554 0.576268 0.040 Uiso 1 1 calc R U . . .
C56 C 0.3189(6) 0.1099(2) 0.48816(14) 0.0181(8) Uani 1 1 d . . . . .
H56 H 0.330924 0.059466 0.490800 0.022 Uiso 1 1 calc R U . . .
C57 C 0.2824(6) 0.1567(2) 0.52491(14) 0.0191(9) Uani 1 1 d . . . . .
C58 C 0.2795(6) 0.2279(2) 0.50848(15) 0.0201(9) Uani 1 1 d . . . . .
H58 H 0.261289 0.270050 0.525823 0.024 Uiso 1 1 calc R U . . .
C59 C 0.3095(6) 0.2232(2) 0.46031(14) 0.0190(9) Uani 1 1 d . . . . .
C60 C 0.3353(6) 0.1499(2) 0.44614(14) 0.0180(8) Uani 1 1 d . . . . .
N61 N 0.2573(5) 0.13786(18) 0.57073(11) 0.0176(7) Uani 1 1 d . . . . .
C62 C 0.2659(8) 0.1923(3) 0.60702(15) 0.0276(10) Uani 1 1 d . . . . .
H62A H 0.149805 0.224139 0.603709 0.033 Uiso 1 1 calc R U . . .
H62B H 0.386915 0.221431 0.606377 0.033 Uiso 1 1 calc R U . . .
C63 C 0.2669(10) 0.1490(3) 0.65084(17) 0.0392(13) Uani 1 1 d . . . . .
H63A H 0.402740 0.143667 0.664980 0.047 Uiso 1 1 calc R U . . .
H63B H 0.185790 0.172527 0.673353 0.047 Uiso 1 1 calc R U . . .
C64 C 0.1823(9) 0.0777(3) 0.63709(15) 0.0322(11) Uani 1 1 d . . . . .
H64A H 0.042015 0.074991 0.643706 0.039 Uiso 1 1 calc R U . . .
H64B H 0.255193 0.038936 0.653976 0.039 Uiso 1 1 calc R U . . .
C65 C 0.2040(7) 0.0718(2) 0.58579(15) 0.0228(9) Uani 1 1 d . . . . .
O66 O 0.1797(5) 0.01879(17) 0.56181(11) 0.0289(7) Uani 1 1 d . . . . .
S2 S 0.32119(18) 0.29726(6) 0.42601(4) 0.0258(2) Uani 1 1 d . . . . .
O67 O 0.3402(6) 0.36055(18) 0.45283(12) 0.0360(8) Uani 1 1 d . . . . .
O68 O 0.4373(6) 0.2860(2) 0.38836(12) 0.0383(9) Uani 1 1 d . . . . .
F69 F 0.1028(4) 0.30004(16) 0.40338(10) 0.0348(7) Uani 1 1 d . . . . .
Si2 Si 0.35089(19) 0.10584(7) 0.38835(4) 0.0227(3) Uani 1 1 d . . . . .
C70 C 0.3148(8) 0.0093(3) 0.39936(17) 0.0341(12) Uani 1 1 d . . . . .
H70A H 0.315892 -0.017140 0.370272 0.051 Uiso 1 1 calc R U . . .
H70B H 0.188233 0.002068 0.412665 0.051 Uiso 1 1 calc R U . . .
H70C H 0.421344 -0.008138 0.420960 0.051 Uiso 1 1 calc R U . . .
C71 C 0.1472(8) 0.1403(3) 0.34782(17) 0.0382(13) Uani 1 1 d . . . . .
H71A H 0.173612 0.190204 0.340110 0.057 Uiso 1 1 calc R U . . .
H71B H 0.022473 0.137364 0.362500 0.057 Uiso 1 1 calc R U . . .
H71C H 0.138716 0.111555 0.319590 0.057 Uiso 1 1 calc R U . . .
C72 C 0.5906(7) 0.1195(3) 0.36270(17) 0.0301(11) Uani 1 1 d . . . . .
H72A H 0.695129 0.095312 0.381710 0.045 Uiso 1 1 calc R U . . .
H72B H 0.619452 0.170705 0.361475 0.045 Uiso 1 1 calc R U . . .
H72C H 0.583349 0.099690 0.331422 0.045 Uiso 1 1 calc R U . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_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 C9 1.990(4) . ?
Fe1 C8 2.042(4) . ?
Fe1 C5 2.047(5) . ?
Fe1 C1 2.047(5) . ?
Fe1 C3 2.050(5) . ?
Fe1 C2 2.051(5) . ?
Fe1 C10 2.059(4) . ?
Fe1 C4 2.059(5) . ?
Fe1 C6 2.074(4) . ?
Fe1 C7 2.104(4) . ?
C1 C5 1.408(8) . ?
C1 C2 1.424(7) . ?
C1 H1 0.9500 . ?
C2 C3 1.403(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.414(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.407(7) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.419(6) . ?
C6 C10 1.437(6) . ?
C6 H6 0.9500 . ?
C7 N11 1.398(5) . ?
C7 C8 1.424(6) . ?
C8 C9 1.431(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.451(6) . ?
C9 S1 1.715(4) . ?
C10 Si1 1.884(4) . ?
N11 C15 1.368(5) . ?
N11 C12 1.468(5) . ?
C12 C13 1.530(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.520(7) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.510(6) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 O16 1.215(6) . ?
S1 O17 1.415(4) . ?
S1 O18 1.418(3) . ?
S1 F19 1.577(3) . ?
Si1 C21 1.855(5) . ?
Si1 C20 1.862(5) . ?
Si1 C22 1.867(5) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
Fe2 C59 1.997(4) . ?
Fe2 C53 2.029(5) . ?
Fe2 C51 2.038(5) . ?
Fe2 C55 2.042(5) . ?
Fe2 C54 2.044(5) . ?
Fe2 C58 2.047(4) . ?
Fe2 C52 2.053(5) . ?
Fe2 C60 2.065(4) . ?
Fe2 C56 2.067(4) . ?
Fe2 C57 2.088(4) . ?
C51 C55 1.385(7) . ?
C51 C52 1.403(8) . ?
C51 H51 0.9500 . ?
C52 C53 1.405(9) . ?
C52 H52 0.9500 . ?
C53 C54 1.412(9) . ?
C53 H53 0.9500 . ?
C54 C55 1.398(8) . ?
C54 H54 0.9500 . ?
C55 H55 0.9500 . ?
C56 C57 1.418(6) . ?
C56 C60 1.444(6) . ?
C56 H56 0.9500 . ?
C57 N61 1.400(5) . ?
C57 C58 1.416(6) . ?
C58 C59 1.433(6) . ?
C58 H58 0.9500 . ?
C59 C60 1.449(6) . ?
C59 S2 1.713(4) . ?
C60 Si2 1.881(4) . ?
N61 C65 1.371(6) . ?
N61 C62 1.465(5) . ?
C62 C63 1.509(6) . ?
C62 H62A 0.9900 . ?
C62 H62B 0.9900 . ?
C63 C64 1.497(7) . ?
C63 H63A 0.9900 . ?
C63 H63B 0.9900 . ?
C64 C65 1.514(6) . ?
C64 H64A 0.9900 . ?
C64 H64B 0.9900 . ?
C65 O66 1.217(5) . ?
S2 O68 1.412(4) . ?
S2 O67 1.419(4) . ?
S2 F69 1.583(3) . ?
Si2 C70 1.856(5) . ?
Si2 C72 1.862(5) . ?
Si2 C71 1.869(5) . ?
C70 H70A 0.9800 . ?
C70 H70B 0.9800 . ?
C70 H70C 0.9800 . ?
C71 H71A 0.9800 . ?
C71 H71B 0.9800 . ?
C71 H71C 0.9800 . ?
C72 H72A 0.9800 . ?
C72 H72B 0.9800 . ?
C72 H72C 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
C9 Fe1 C8 41.55(16) . . ?
C9 Fe1 C5 142.54(19) . . ?
C8 Fe1 C5 110.88(19) . . ?
C9 Fe1 C1 114.77(19) . . ?
C8 Fe1 C1 109.96(19) . . ?
C5 Fe1 C1 40.2(2) . . ?
C9 Fe1 C3 138.68(19) . . ?
C8 Fe1 C3 177.85(19) . . ?
C5 Fe1 C3 67.8(2) . . ?
C1 Fe1 C3 67.9(2) . . ?
C9 Fe1 C2 113.35(19) . . ?
C8 Fe1 C2 138.1(2) . . ?
C5 Fe1 C2 67.8(2) . . ?
C1 Fe1 C2 40.7(2) . . ?
C3 Fe1 C2 40.0(2) . . ?
C9 Fe1 C10 41.95(16) . . ?
C8 Fe1 C10 70.93(16) . . ?
C5 Fe1 C10 174.5(2) . . ?
C1 Fe1 C10 144.7(2) . . ?
C3 Fe1 C10 110.58(18) . . ?
C2 Fe1 C10 114.62(19) . . ?
C9 Fe1 C4 177.34(19) . . ?
C8 Fe1 C4 139.65(19) . . ?
C5 Fe1 C4 40.1(2) . . ?
C1 Fe1 C4 67.5(2) . . ?
C3 Fe1 C4 40.3(2) . . ?
C2 Fe1 C4 67.3(2) . . ?
C10 Fe1 C4 135.39(18) . . ?
C9 Fe1 C6 67.77(16) . . ?
C8 Fe1 C6 68.12(16) . . ?
C5 Fe1 C6 134.6(2) . . ?
C1 Fe1 C6 174.2(2) . . ?
C3 Fe1 C6 114.02(18) . . ?
C2 Fe1 C6 144.16(19) . . ?
C10 Fe1 C6 40.68(16) . . ?
C4 Fe1 C6 110.09(18) . . ?
C9 Fe1 C7 67.63(16) . . ?
C8 Fe1 C7 40.14(16) . . ?
C5 Fe1 C7 109.04(19) . . ?
C1 Fe1 C7 135.4(2) . . ?
C3 Fe1 C7 141.63(19) . . ?
C2 Fe1 C7 176.1(2) . . ?
C10 Fe1 C7 68.76(16) . . ?
C4 Fe1 C7 111.87(19) . . ?
C6 Fe1 C7 39.70(15) . . ?
C5 C1 C2 107.5(5) . . ?
C5 C1 Fe1 69.9(3) . . ?
C2 C1 Fe1 69.8(3) . . ?
C5 C1 H1 126.2 . . ?
C2 C1 H1 126.2 . . ?
Fe1 C1 H1 125.6 . . ?
C3 C2 C1 108.1(5) . . ?
C3 C2 Fe1 69.9(3) . . ?
C1 C2 Fe1 69.5(3) . . ?
C3 C2 H2 126.0 . . ?
C1 C2 H2 126.0 . . ?
Fe1 C2 H2 126.2 . . ?
C2 C3 C4 108.0(4) . . ?
C2 C3 Fe1 70.1(3) . . ?
C4 C3 Fe1 70.2(3) . . ?
C2 C3 H3 126.0 . . ?
C4 C3 H3 126.0 . . ?
Fe1 C3 H3 125.3 . . ?
C5 C4 C3 108.1(5) . . ?
C5 C4 Fe1 69.5(3) . . ?
C3 C4 Fe1 69.5(3) . . ?
C5 C4 H4 126.0 . . ?
C3 C4 H4 126.0 . . ?
Fe1 C4 H4 126.6 . . ?
C4 C5 C1 108.3(5) . . ?
C4 C5 Fe1 70.4(3) . . ?
C1 C5 Fe1 69.9(3) . . ?
C4 C5 H5 125.9 . . ?
C1 C5 H5 125.9 . . ?
Fe1 C5 H5 125.4 . . ?
C7 C6 C10 110.8(4) . . ?
C7 C6 Fe1 71.3(2) . . ?
C10 C6 Fe1 69.1(2) . . ?
C7 C6 H6 124.6 . . ?
C10 C6 H6 124.6 . . ?
Fe1 C6 H6 126.6 . . ?
N11 C7 C6 124.3(4) . . ?
N11 C7 C8 127.3(4) . . ?
C6 C7 C8 108.4(4) . . ?
N11 C7 Fe1 128.1(3) . . ?
C6 C7 Fe1 69.0(2) . . ?
C8 C7 Fe1 67.6(2) . . ?
C7 C8 C9 106.0(3) . . ?
C7 C8 Fe1 72.3(2) . . ?
C9 C8 Fe1 67.3(2) . . ?
C7 C8 H8 127.0 . . ?
C9 C8 H8 127.0 . . ?
Fe1 C8 H8 125.0 . . ?
C8 C9 C10 111.3(3) . . ?
C8 C9 S1 122.5(3) . . ?
C10 C9 S1 126.0(3) . . ?
C8 C9 Fe1 71.2(2) . . ?
C10 C9 Fe1 71.6(2) . . ?
S1 C9 Fe1 120.4(2) . . ?
C6 C10 C9 103.4(3) . . ?
C6 C10 Si1 123.6(3) . . ?
C9 C10 Si1 132.4(3) . . ?
C6 C10 Fe1 70.2(2) . . ?
C9 C10 Fe1 66.5(2) . . ?
Si1 C10 Fe1 133.1(2) . . ?
C15 N11 C7 125.1(4) . . ?
C15 N11 C12 113.2(4) . . ?
C7 N11 C12 121.4(3) . . ?
N11 C12 C13 102.7(4) . . ?
N11 C12 H12A 111.2 . . ?
C13 C12 H12A 111.2 . . ?
N11 C12 H12B 111.2 . . ?
C13 C12 H12B 111.2 . . ?
H12A C12 H12B 109.1 . . ?
C14 C13 C12 104.1(4) . . ?
C14 C13 H13A 110.9 . . ?
C12 C13 H13A 110.9 . . ?
C14 C13 H13B 110.9 . . ?
C12 C13 H13B 110.9 . . ?
H13A C13 H13B 109.0 . . ?
C15 C14 C13 104.4(4) . . ?
C15 C14 H14A 110.9 . . ?
C13 C14 H14A 110.9 . . ?
C15 C14 H14B 110.9 . . ?
C13 C14 H14B 110.9 . . ?
H14A C14 H14B 108.9 . . ?
O16 C15 N11 125.5(4) . . ?
O16 C15 C14 126.9(4) . . ?
N11 C15 C14 107.6(4) . . ?
O17 S1 O18 120.7(2) . . ?
O17 S1 F19 104.8(2) . . ?
O18 S1 F19 103.8(2) . . ?
O17 S1 C9 112.0(2) . . ?
O18 S1 C9 112.1(2) . . ?
F19 S1 C9 100.83(19) . . ?
C21 Si1 C20 110.6(2) . . ?
C21 Si1 C22 109.3(2) . . ?
C20 Si1 C22 108.9(2) . . ?
C21 Si1 C10 112.7(2) . . ?
C20 Si1 C10 109.1(2) . . ?
C22 Si1 C10 105.9(2) . . ?
Si1 C20 H20A 109.5 . . ?
Si1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
Si1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
Si1 C21 H21A 109.5 . . ?
Si1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
Si1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
Si1 C22 H22A 109.5 . . ?
Si1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
Si1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C59 Fe2 C53 110.9(2) . . ?
C59 Fe2 C51 157.0(2) . . ?
C53 Fe2 C51 67.5(2) . . ?
C59 Fe2 C55 162.8(2) . . ?
C53 Fe2 C55 67.5(2) . . ?
C51 Fe2 C55 39.7(2) . . ?
C59 Fe2 C54 127.5(2) . . ?
C53 Fe2 C54 40.6(3) . . ?
C51 Fe2 C54 67.3(2) . . ?
C55 Fe2 C54 40.0(2) . . ?
C59 Fe2 C58 41.47(17) . . ?
C53 Fe2 C58 120.8(2) . . ?
C51 Fe2 C58 160.0(2) . . ?
C55 Fe2 C58 123.4(2) . . ?
C54 Fe2 C58 106.2(2) . . ?
C59 Fe2 C52 123.5(2) . . ?
C53 Fe2 C52 40.3(3) . . ?
C51 Fe2 C52 40.1(2) . . ?
C55 Fe2 C52 67.1(2) . . ?
C54 Fe2 C52 67.7(2) . . ?
C58 Fe2 C52 157.0(2) . . ?
C59 Fe2 C60 41.74(17) . . ?
C53 Fe2 C60 128.8(2) . . ?
C51 Fe2 C60 119.99(19) . . ?
C55 Fe2 C60 152.8(2) . . ?
C54 Fe2 C60 166.3(2) . . ?
C58 Fe2 C60 70.73(17) . . ?
C52 Fe2 C60 109.6(2) . . ?
C59 Fe2 C56 67.93(17) . . ?
C53 Fe2 C56 166.0(2) . . ?
C51 Fe2 C56 107.79(19) . . ?
C55 Fe2 C56 118.06(19) . . ?
C54 Fe2 C56 151.5(2) . . ?
C58 Fe2 C56 68.26(17) . . ?
C52 Fe2 C56 127.8(2) . . ?
C60 Fe2 C56 40.91(16) . . ?
C59 Fe2 C57 67.55(17) . . ?
C53 Fe2 C57 153.7(2) . . ?
C51 Fe2 C57 124.6(2) . . ?
C55 Fe2 C57 105.94(19) . . ?
C54 Fe2 C57 117.9(2) . . ?
C58 Fe2 C57 40.03(17) . . ?
C52 Fe2 C57 162.7(2) . . ?
C60 Fe2 C57 68.83(16) . . ?
C56 Fe2 C57 39.91(16) . . ?
C55 C51 C52 108.6(5) . . ?
C55 C51 Fe2 70.3(3) . . ?
C52 C51 Fe2 70.5(3) . . ?
C55 C51 H51 125.7 . . ?
C52 C51 H51 125.7 . . ?
Fe2 C51 H51 125.0 . . ?
C51 C52 C53 107.2(5) . . ?
C51 C52 Fe2 69.4(3) . . ?
C53 C52 Fe2 69.0(3) . . ?
C51 C52 H52 126.4 . . ?
C53 C52 H52 126.4 . . ?
Fe2 C52 H52 126.8 . . ?
C52 C53 C54 108.3(5) . . ?
C52 C53 Fe2 70.8(3) . . ?
C54 C53 Fe2 70.3(3) . . ?
C52 C53 H53 125.9 . . ?
C54 C53 H53 125.9 . . ?
Fe2 C53 H53 124.7 . . ?
C55 C54 C53 107.1(5) . . ?
C55 C54 Fe2 69.9(3) . . ?
C53 C54 Fe2 69.2(3) . . ?
C55 C54 H54 126.4 . . ?
C53 C54 H54 126.4 . . ?
Fe2 C54 H54 126.0 . . ?
C51 C55 C54 108.8(5) . . ?
C51 C55 Fe2 70.0(3) . . ?
C54 C55 Fe2 70.1(3) . . ?
C51 C55 H55 125.6 . . ?
C54 C55 H55 125.6 . . ?
Fe2 C55 H55 125.9 . . ?
C57 C56 C60 110.2(4) . . ?
C57 C56 Fe2 70.9(2) . . ?
C60 C56 Fe2 69.5(2) . . ?
C57 C56 H56 124.9 . . ?
C60 C56 H56 124.9 . . ?
Fe2 C56 H56 126.4 . . ?
N61 C57 C58 123.9(4) . . ?
N61 C57 C56 127.0(4) . . ?
C58 C57 C56 109.1(4) . . ?
N61 C57 Fe2 127.3(3) . . ?
C58 C57 Fe2 68.4(2) . . ?
C56 C57 Fe2 69.2(2) . . ?
C57 C58 C59 105.8(4) . . ?
C57 C58 Fe2 71.5(3) . . ?
C59 C58 Fe2 67.4(2) . . ?
C57 C58 H58 127.1 . . ?
C59 C58 H58 127.1 . . ?
Fe2 C58 H58 125.5 . . ?
C58 C59 C60 111.4(4) . . ?
C58 C59 S2 122.4(3) . . ?
C60 C59 S2 126.2(3) . . ?
C58 C59 Fe2 71.1(2) . . ?
C60 C59 Fe2 71.6(2) . . ?
S2 C59 Fe2 122.6(2) . . ?
C56 C60 C59 103.5(3) . . ?
C56 C60 Si2 122.8(3) . . ?
C59 C60 Si2 133.3(3) . . ?
C56 C60 Fe2 69.6(2) . . ?
C59 C60 Fe2 66.6(2) . . ?
Si2 C60 Fe2 133.1(2) . . ?
C65 N61 C57 125.8(4) . . ?
C65 N61 C62 113.3(3) . . ?
C57 N61 C62 120.6(4) . . ?
N61 C62 C63 103.4(4) . . ?
N61 C62 H62A 111.1 . . ?
C63 C62 H62A 111.1 . . ?
N61 C62 H62B 111.1 . . ?
C63 C62 H62B 111.1 . . ?
H62A C62 H62B 109.0 . . ?
C64 C63 C62 106.0(4) . . ?
C64 C63 H63A 110.5 . . ?
C62 C63 H63A 110.5 . . ?
C64 C63 H63B 110.5 . . ?
C62 C63 H63B 110.5 . . ?
H63A C63 H63B 108.7 . . ?
C63 C64 C65 105.4(4) . . ?
C63 C64 H64A 110.7 . . ?
C65 C64 H64A 110.7 . . ?
C63 C64 H64B 110.7 . . ?
C65 C64 H64B 110.7 . . ?
H64A C64 H64B 108.8 . . ?
O66 C65 N61 125.6(4) . . ?
O66 C65 C64 127.3(4) . . ?
N61 C65 C64 107.2(4) . . ?
O68 S2 O67 121.1(2) . . ?
O68 S2 F69 104.2(2) . . ?
O67 S2 F69 104.2(2) . . ?
O68 S2 C59 112.5(2) . . ?
O67 S2 C59 111.3(2) . . ?
F69 S2 C59 100.74(19) . . ?
C70 Si2 C72 109.5(2) . . ?
C70 Si2 C71 110.1(3) . . ?
C72 Si2 C71 109.4(2) . . ?
C70 Si2 C60 104.8(2) . . ?
C72 Si2 C60 113.9(2) . . ?
C71 Si2 C60 108.9(2) . . ?
Si2 C70 H70A 109.5 . . ?
Si2 C70 H70B 109.5 . . ?
H70A C70 H70B 109.5 . . ?
Si2 C70 H70C 109.5 . . ?
H70A C70 H70C 109.5 . . ?
H70B C70 H70C 109.5 . . ?
Si2 C71 H71A 109.5 . . ?
Si2 C71 H71B 109.5 . . ?
H71A C71 H71B 109.5 . . ?
Si2 C71 H71C 109.5 . . ?
H71A C71 H71C 109.5 . . ?
H71B C71 H71C 109.5 . . ?
Si2 C72 H72A 109.5 . . ?
Si2 C72 H72B 109.5 . . ?
H72A C72 H72B 109.5 . . ?
Si2 C72 H72C 109.5 . . ?
H72A C72 H72C 109.5 . . ?
H72B C72 H72C 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
C5 C1 C2 C3 -0.4(6) . . . . ?
Fe1 C1 C2 C3 59.5(3) . . . . ?
C5 C1 C2 Fe1 -60.0(4) . . . . ?
C1 C2 C3 C4 1.0(5) . . . . ?
Fe1 C2 C3 C4 60.3(3) . . . . ?
C1 C2 C3 Fe1 -59.2(3) . . . . ?
C2 C3 C4 C5 -1.2(5) . . . . ?
Fe1 C3 C4 C5 58.9(3) . . . . ?
C2 C3 C4 Fe1 -60.1(3) . . . . ?
C3 C4 C5 C1 0.9(6) . . . . ?
Fe1 C4 C5 C1 59.9(4) . . . . ?
C3 C4 C5 Fe1 -59.0(3) . . . . ?
C2 C1 C5 C4 -0.3(6) . . . . ?
Fe1 C1 C5 C4 -60.2(3) . . . . ?
C2 C1 C5 Fe1 59.9(3) . . . . ?
C10 C6 C7 N11 -179.6(4) . . . . ?
Fe1 C6 C7 N11 122.5(4) . . . . ?
C10 C6 C7 C8 1.8(5) . . . . ?
Fe1 C6 C7 C8 -56.1(3) . . . . ?
C10 C6 C7 Fe1 57.9(3) . . . . ?
N11 C7 C8 C9 179.3(4) . . . . ?
C6 C7 C8 C9 -2.2(5) . . . . ?
Fe1 C7 C8 C9 -59.1(3) . . . . ?
N11 C7 C8 Fe1 -121.6(4) . . . . ?
C6 C7 C8 Fe1 56.9(3) . . . . ?
C7 C8 C9 C10 1.8(5) . . . . ?
Fe1 C8 C9 C10 -60.5(3) . . . . ?
C7 C8 C9 S1 177.0(3) . . . . ?
Fe1 C8 C9 S1 114.6(3) . . . . ?
C7 C8 C9 Fe1 62.4(3) . . . . ?
C7 C6 C10 C9 -0.6(5) . . . . ?
Fe1 C6 C10 C9 58.5(3) . . . . ?
C7 C6 C10 Si1 171.6(3) . . . . ?
Fe1 C6 C10 Si1 -129.2(3) . . . . ?
C7 C6 C10 Fe1 -59.2(3) . . . . ?
C8 C9 C10 C6 -0.8(5) . . . . ?
S1 C9 C10 C6 -175.7(3) . . . . ?
Fe1 C9 C10 C6 -61.1(3) . . . . ?
C8 C9 C10 Si1 -172.0(3) . . . . ?
S1 C9 C10 Si1 13.1(6) . . . . ?
Fe1 C9 C10 Si1 127.7(4) . . . . ?
C8 C9 C10 Fe1 60.3(3) . . . . ?
S1 C9 C10 Fe1 -114.6(4) . . . . ?
C6 C7 N11 C15 -175.4(4) . . . . ?
C8 C7 N11 C15 2.9(7) . . . . ?
Fe1 C7 N11 C15 -86.4(5) . . . . ?
C6 C7 N11 C12 -3.0(6) . . . . ?
C8 C7 N11 C12 175.4(4) . . . . ?
Fe1 C7 N11 C12 86.1(5) . . . . ?
C15 N11 C12 C13 -18.5(6) . . . . ?
C7 N11 C12 C13 168.2(4) . . . . ?
N11 C12 C13 C14 27.1(6) . . . . ?
C12 C13 C14 C15 -26.6(6) . . . . ?
C7 N11 C15 O16 -2.8(8) . . . . ?
C12 N11 C15 O16 -175.8(5) . . . . ?
C7 N11 C15 C14 174.7(4) . . . . ?
C12 N11 C15 C14 1.7(6) . . . . ?
C13 C14 C15 O16 -166.4(5) . . . . ?
C13 C14 C15 N11 16.1(6) . . . . ?
C8 C9 S1 O17 -14.3(5) . . . . ?
C10 C9 S1 O17 160.1(4) . . . . ?
Fe1 C9 S1 O17 71.6(3) . . . . ?
C8 C9 S1 O18 -153.5(4) . . . . ?
C10 C9 S1 O18 20.9(5) . . . . ?
Fe1 C9 S1 O18 -67.6(3) . . . . ?
C8 C9 S1 F19 96.7(4) . . . . ?
C10 C9 S1 F19 -88.9(4) . . . . ?
Fe1 C9 S1 F19 -177.4(2) . . . . ?
C6 C10 Si1 C21 112.1(4) . . . . ?
C9 C10 Si1 C21 -78.2(5) . . . . ?
Fe1 C10 Si1 C21 18.3(4) . . . . ?
C6 C10 Si1 C20 -124.6(4) . . . . ?
C9 C10 Si1 C20 45.2(5) . . . . ?
Fe1 C10 Si1 C20 141.7(3) . . . . ?
C6 C10 Si1 C22 -7.5(4) . . . . ?
C9 C10 Si1 C22 162.2(4) . . . . ?
Fe1 C10 Si1 C22 -101.2(3) . . . . ?
C55 C51 C52 C53 -1.5(6) . . . . ?
Fe2 C51 C52 C53 58.8(4) . . . . ?
C55 C51 C52 Fe2 -60.3(3) . . . . ?
C51 C52 C53 C54 1.5(6) . . . . ?
Fe2 C52 C53 C54 60.6(4) . . . . ?
C51 C52 C53 Fe2 -59.0(4) . . . . ?
C52 C53 C54 C55 -1.0(6) . . . . ?
Fe2 C53 C54 C55 59.9(4) . . . . ?
C52 C53 C54 Fe2 -60.9(4) . . . . ?
C52 C51 C55 C54 0.9(6) . . . . ?
Fe2 C51 C55 C54 -59.5(4) . . . . ?
C52 C51 C55 Fe2 60.4(4) . . . . ?
C53 C54 C55 C51 0.0(6) . . . . ?
Fe2 C54 C55 C51 59.5(3) . . . . ?
C53 C54 C55 Fe2 -59.4(3) . . . . ?
C60 C56 C57 N61 179.8(4) . . . . ?
Fe2 C56 C57 N61 -121.7(4) . . . . ?
C60 C56 C57 C58 -1.6(5) . . . . ?
Fe2 C56 C57 C58 56.8(3) . . . . ?
C60 C56 C57 Fe2 -58.5(3) . . . . ?
N61 C57 C58 C59 -179.8(4) . . . . ?
C56 C57 C58 C59 1.6(5) . . . . ?
Fe2 C57 C58 C59 58.9(3) . . . . ?
N61 C57 C58 Fe2 121.3(4) . . . . ?
C56 C57 C58 Fe2 -57.3(3) . . . . ?
C57 C58 C59 C60 -1.1(5) . . . . ?
Fe2 C58 C59 C60 60.6(3) . . . . ?
C57 C58 C59 S2 -178.9(3) . . . . ?
Fe2 C58 C59 S2 -117.2(3) . . . . ?
C57 C58 C59 Fe2 -61.7(3) . . . . ?
C57 C56 C60 C59 0.9(5) . . . . ?
Fe2 C56 C60 C59 -58.4(3) . . . . ?
C57 C56 C60 Si2 -171.9(3) . . . . ?
Fe2 C56 C60 Si2 128.9(3) . . . . ?
C57 C56 C60 Fe2 59.3(3) . . . . ?
C58 C59 C60 C56 0.1(5) . . . . ?
S2 C59 C60 C56 177.8(3) . . . . ?
Fe2 C59 C60 C56 60.4(3) . . . . ?
C58 C59 C60 Si2 171.8(3) . . . . ?
S2 C59 C60 Si2 -10.5(6) . . . . ?
Fe2 C59 C60 Si2 -127.9(4) . . . . ?
C58 C59 C60 Fe2 -60.3(3) . . . . ?
S2 C59 C60 Fe2 117.4(4) . . . . ?
C58 C57 N61 C65 160.4(4) . . . . ?
C56 C57 N61 C65 -21.3(7) . . . . ?
Fe2 C57 N61 C65 -112.2(4) . . . . ?
C58 C57 N61 C62 -12.5(6) . . . . ?
C56 C57 N61 C62 165.8(4) . . . . ?
Fe2 C57 N61 C62 74.9(5) . . . . ?
C65 N61 C62 C63 15.4(5) . . . . ?
C57 N61 C62 C63 -170.8(4) . . . . ?
N61 C62 C63 C64 -21.3(6) . . . . ?
C62 C63 C64 C65 20.1(6) . . . . ?
C57 N61 C65 O66 3.7(7) . . . . ?
C62 N61 C65 O66 177.1(5) . . . . ?
C57 N61 C65 C64 -176.4(4) . . . . ?
C62 N61 C65 C64 -3.0(5) . . . . ?
C63 C64 C65 O66 169.0(5) . . . . ?
C63 C64 C65 N61 -10.9(6) . . . . ?
C58 C59 S2 O68 152.2(4) . . . . ?
C60 C59 S2 O68 -25.3(5) . . . . ?
Fe2 C59 S2 O68 65.0(3) . . . . ?
C58 C59 S2 O67 12.6(4) . . . . ?
C60 C59 S2 O67 -164.8(4) . . . . ?
Fe2 C59 S2 O67 -74.6(3) . . . . ?
C58 C59 S2 F69 -97.4(4) . . . . ?
C60 C59 S2 F69 85.1(4) . . . . ?
Fe2 C59 S2 F69 175.4(2) . . . . ?
C56 C60 Si2 C70 5.5(4) . . . . ?
C59 C60 Si2 C70 -164.8(4) . . . . ?
Fe2 C60 Si2 C70 97.5(3) . . . . ?
C56 C60 Si2 C72 -114.2(4) . . . . ?
C59 C60 Si2 C72 75.5(5) . . . . ?
Fe2 C60 Si2 C72 -22.2(4) . . . . ?
C56 C60 Si2 C71 123.4(4) . . . . ?
C59 C60 Si2 C71 -46.9(5) . . . . ?
Fe2 C60 Si2 C71 -144.6(3) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


####################################################################### 
# 
# 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_WE15831
_database_code_depnum_ccdc_archive 'CCDC 2189767'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;ISCR
France
;
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2022-09-25 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 26 juillet 2021                                          #
#------------------------------------------------------------------------------#


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H20 F4 Fe O2 S Si'
_chemical_formula_sum            'C20 H20 F4 Fe O2 S Si'
_chemical_formula_weight         484.36
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9209(7)
_cell_length_b                   9.9176(8)
_cell_length_c                   12.6295(10)
_cell_angle_alpha                88.185(3)
_cell_angle_beta                 75.906(3)
_cell_angle_gamma                76.235(3)
_cell_volume                     1052.21(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4297
_cell_measurement_theta_min      2.4229
_cell_measurement_theta_max      27.4408
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      0.0223171
_diffrn_orient_matrix_UB_21      0.0705178
_diffrn_orient_matrix_UB_31      0.0931715
_diffrn_orient_matrix_UB_12      -0.0948895
_diffrn_orient_matrix_UB_22      0.0289416
_diffrn_orient_matrix_UB_32      -0.0306775
_diffrn_orient_matrix_UB_13      -0.0335144
_diffrn_orient_matrix_UB_23      -0.0666630
_diffrn_orient_matrix_UB_33      0.0331011


#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.180
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             496
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.756
_exptl_absorpt_correction_T_max  0.847

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

# Software                   : BIS 2014.5.0.0/23-May-2014 && APEX2_2014.11-0   #
# Number of scans            :        4                                        #
# Total number of frames     :      374                                        #
# Total length of scans      :   374.00 (deg.)                                 #
# Rotation speed             :    10.00 sec./deg.                              #
# Total exposition time      :      1 h   2.3 min.                             #
#                                                                              #
#    Scan  Time(s) Width DX(mm) Frames Range 2Theta  Omega    Phi    Chi  T(K) #
#..............................................................................#
#                                                                              #
#  1 Omega   10.0  1.00    35.0   105  105.0   14.9   14.5  240.0  305.3 150.0 #
#  2 Omega   10.0  1.00    35.0   105  105.0   14.9   14.5    0.0  305.3 150.0 #
#  3 Omega   10.0  1.00    35.0   105  105.0   14.9   14.5  120.0  305.3 150.0 #
#  4 Phi     10.0  1.00    35.0    59   59.0   14.9   10.4  360.0  337.0 150.0 #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'APEXII Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 CCD-LDI-APEX2
_diffrn_detector_area_resol_mean 10.4167
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_source_current           1.0
_diffrn_source_voltage           50.0
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0370
_diffrn_reflns_av_r_equivalents  0.0234
_diffrn_reflns_number            9401
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.423
_diffrn_reflns_theta_max         27.503
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.976
_reflns_number_total             4724
_reflns_number_gt                3882
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (G. Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2020)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0885P)²+1.9603P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         4724
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1441
_refine_ls_wR_factor_gt          0.1324
_refine_ls_goodness_of_fit_ref   0.905
_refine_ls_restrained_S_all      0.905
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         1.457
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.083

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'
F F 0.0171 0.0103 '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'
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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.70706(4) 0.77248(4) 0.65501(3) 0.02232(14) Uani 1 1 d . . . . .
C1A C 0.7340(4) 0.7808(4) 0.4889(2) 0.0345(6) Uani 0.697(4) 1 d G . P A 1
H1A H 0.823344 0.733000 0.434821 0.041 Uiso 0.697(4) 1 calc R U P A 1
C2A C 0.7129(4) 0.9153(4) 0.5341(3) 0.0345(6) Uani 0.697(4) 1 d G . P A 1
H2A H 0.785786 0.973200 0.515589 0.041 Uiso 0.697(4) 1 calc R U P A 1
C3A C 0.5639(5) 0.9479(3) 0.6119(3) 0.0345(6) Uani 0.697(4) 1 d G . P A 1
H3A H 0.519548 1.031498 0.654525 0.041 Uiso 0.697(4) 1 calc R U P A 1
C4A C 0.4928(3) 0.8336(5) 0.6147(3) 0.0345(6) Uani 0.697(4) 1 d G . P A 1
H4A H 0.392562 0.827330 0.659624 0.041 Uiso 0.697(4) 1 calc R U P A 1
C5A C 0.5979(5) 0.7303(3) 0.5387(3) 0.0345(6) Uani 0.697(4) 1 d G . P A 1
H5A H 0.580319 0.642847 0.523840 0.041 Uiso 0.697(4) 1 calc R U P A 1
C1B C 0.7424(7) 0.8564(11) 0.5020(7) 0.0345(6) Uani 0.303(4) 1 d G . P A 2
H1B H 0.842581 0.860380 0.455738 0.041 Uiso 0.303(4) 1 calc R U P A 2
C2B C 0.6420(12) 0.9610(7) 0.5787(8) 0.0345(6) Uani 0.303(4) 1 d G . P A 2
H2B H 0.663223 1.047238 0.592835 0.041 Uiso 0.303(4) 1 calc R U P A 2
C3B C 0.5043(9) 0.9140(9) 0.6307(6) 0.0345(6) Uani 0.303(4) 1 d G . P A 2
H3B H 0.417263 0.963329 0.685638 0.041 Uiso 0.303(4) 1 calc R U P A 2
C4B C 0.5196(10) 0.7804(9) 0.5860(8) 0.0345(6) Uani 0.303(4) 1 d G . P A 2
H4B H 0.444609 0.724613 0.605895 0.041 Uiso 0.303(4) 1 calc R U P A 2
C5B C 0.6668(11) 0.7448(7) 0.5065(7) 0.0345(6) Uani 0.303(4) 1 d G . P A 2
H5B H 0.707470 0.660987 0.463809 0.041 Uiso 0.303(4) 1 calc R U P A 2
C6 C 0.8205(3) 0.8084(3) 0.7716(2) 0.0234(6) Uani 1 1 d . . . . .
C7 C 0.6800(4) 0.7611(3) 0.8208(2) 0.0265(6) Uani 1 1 d . . . . .
H7 H 0.593814 0.811245 0.875917 0.032 Uiso 1 1 calc R U . . .
C8 C 0.6869(3) 0.6289(3) 0.7760(2) 0.0253(6) Uani 1 1 d . . . . .
C9 C 0.8345(3) 0.5888(3) 0.6964(3) 0.0269(6) Uani 1 1 d . . . . .
H9 H 0.872301 0.505474 0.653035 0.032 Uiso 1 1 calc R U . . .
C10 C 0.9146(3) 0.6982(3) 0.6944(2) 0.0239(6) Uani 1 1 d . . . . .
Si1 Si 0.86563(10) 0.97256(9) 0.81331(7) 0.0302(2) Uani 1 1 d . . . . .
C11 C 1.0550(5) 0.9207(4) 0.8588(3) 0.0448(9) Uani 1 1 d . . . . .
H11A H 1.140353 0.871068 0.798802 0.067 Uiso 1 1 calc R U . . .
H11B H 1.041067 0.859856 0.921363 0.067 Uiso 1 1 calc R U . . .
H11C H 1.083035 1.003808 0.880214 0.067 Uiso 1 1 calc R U . . .
C12 C 0.8795(5) 1.1040(4) 0.7052(3) 0.0460(9) Uani 1 1 d . . . . .
H12A H 0.774670 1.139835 0.690204 0.069 Uiso 1 1 calc R U . . .
H12B H 0.955478 1.060811 0.638378 0.069 Uiso 1 1 calc R U . . .
H12C H 0.915724 1.180618 0.729922 0.069 Uiso 1 1 calc R U . . .
C13 C 0.6970(5) 1.0516(4) 0.9288(3) 0.0494(10) Uani 1 1 d . . . . .
H13A H 0.714807 1.137461 0.954135 0.074 Uiso 1 1 calc R U . . .
H13B H 0.689220 0.986356 0.988674 0.074 Uiso 1 1 calc R U . . .
H13C H 0.597868 1.072571 0.904406 0.074 Uiso 1 1 calc R U . . .
S1 S 1.09433(8) 0.69580(8) 0.60490(7) 0.03010(19) Uani 1 1 d . . . . .
O14 O 1.1261(3) 0.6006(3) 0.5173(3) 0.0602(9) Uani 1 1 d . . . . .
F16 F 1.2118(2) 0.6263(2) 0.6761(2) 0.0568(7) Uani 1 1 d . . . . .
O15 O 1.1211(3) 0.8301(2) 0.58667(19) 0.0355(5) Uani 1 1 d . . . . .
C17 C 0.5605(4) 0.5507(3) 0.8011(3) 0.0274(6) Uani 1 1 d . . . . .
C18 C 0.5656(4) 0.4423(3) 0.7311(3) 0.0318(7) Uani 1 1 d . . . . .
H18 H 0.651044 0.418560 0.667943 0.038 Uiso 1 1 calc R U . . .
C19 C 0.4478(4) 0.3694(3) 0.7527(3) 0.0356(7) Uani 1 1 d . . . . .
H19 H 0.451957 0.296269 0.704437 0.043 Uiso 1 1 calc R U . . .
C20 C 0.3238(4) 0.4035(3) 0.8451(3) 0.0355(7) Uani 1 1 d . . . . .
C21 C 0.3170(5) 0.5096(4) 0.9147(3) 0.0455(9) Uani 1 1 d . . . . .
H21 H 0.231263 0.532880 0.977690 0.055 Uiso 1 1 calc R U . . .
C22 C 0.4352(4) 0.5828(4) 0.8931(3) 0.0412(8) Uani 1 1 d . . . . .
H22 H 0.430185 0.655650 0.941884 0.049 Uiso 1 1 calc R U . . .
C23 C 0.1939(5) 0.3275(4) 0.8655(4) 0.0497(10) Uani 1 1 d . . . . .
F24 F 0.1252(4) 0.3215(4) 0.9692(3) 0.1040(13) Uani 1 1 d . . . . .
F25 F 0.0814(5) 0.3802(5) 0.8194(4) 0.136(2) Uani 1 1 d . . . . .
F26 F 0.2440(4) 0.1976(4) 0.8313(4) 0.1325(19) Uani 1 1 d . . . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_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 C10 1.999(3) . ?
Fe1 C9 2.032(3) . ?
Fe1 C5B 2.032(7) . ?
Fe1 C3A 2.043(3) . ?
Fe1 C4A 2.045(3) . ?
Fe1 C2A 2.049(3) . ?
Fe1 C4B 2.050(7) . ?
Fe1 C7 2.051(3) . ?
Fe1 C5A 2.051(3) . ?
Fe1 C1A 2.054(3) . ?
Fe1 C8 2.060(3) . ?
Fe1 C6 2.061(3) . ?
C1A C2A 1.4200 . ?
C1A C5A 1.4200 . ?
C1A H1A 0.9500 . ?
C2A C3A 1.4200 . ?
C2A H2A 0.9500 . ?
C3A C4A 1.4200 . ?
C3A H3A 0.9500 . ?
C4A C5A 1.4200 . ?
C4A H4A 0.9500 . ?
C5A H5A 0.9500 . ?
C1B C5B 1.4200 . ?
C1B C2B 1.4200 . ?
C1B H1B 0.9500 . ?
C2B C3B 1.4200 . ?
C2B H2B 0.9500 . ?
C3B C4B 1.4200 . ?
C3B H3B 0.9500 . ?
C4B C5B 1.4200 . ?
C4B H4B 0.9500 . ?
C5B H5B 0.9500 . ?
C6 C7 1.434(4) . ?
C6 C10 1.443(4) . ?
C6 Si1 1.887(3) . ?
C7 C8 1.427(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.426(4) . ?
C8 C17 1.483(4) . ?
C9 C10 1.431(4) . ?
C9 H9 0.9500 . ?
C10 S1 1.718(3) . ?
Si1 C13 1.856(4) . ?
Si1 C12 1.861(4) . ?
Si1 C11 1.868(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
S1 O14 1.408(3) . ?
S1 O15 1.411(2) . ?
S1 F16 1.568(2) . ?
C17 C22 1.388(5) . ?
C17 C18 1.398(4) . ?
C18 C19 1.383(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.385(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.374(5) . ?
C20 C23 1.495(4) . ?
C21 C22 1.387(5) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 F25 1.278(5) . ?
C23 F26 1.309(5) . ?
C23 F24 1.310(5) . ?

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 Fe1 C9 41.58(11) . . ?
C10 Fe1 C5B 124.6(3) . . ?
C9 Fe1 C5B 107.9(2) . . ?
C10 Fe1 C3A 143.59(14) . . ?
C9 Fe1 C3A 174.82(14) . . ?
C10 Fe1 C4A 175.73(14) . . ?
C9 Fe1 C4A 134.17(14) . . ?
C3A Fe1 C4A 40.65(6) . . ?
C10 Fe1 C2A 114.77(12) . . ?
C9 Fe1 C2A 141.60(16) . . ?
C3A Fe1 C2A 40.61(6) . . ?
C4A Fe1 C2A 68.29(7) . . ?
C10 Fe1 C4B 159.3(3) . . ?
C9 Fe1 C4B 121.2(2) . . ?
C5B Fe1 C4B 40.71(13) . . ?
C10 Fe1 C7 68.00(12) . . ?
C9 Fe1 C7 68.52(12) . . ?
C5B Fe1 C7 158.1(3) . . ?
C3A Fe1 C7 112.38(12) . . ?
C4A Fe1 C7 111.81(12) . . ?
C2A Fe1 C7 140.35(15) . . ?
C4B Fe1 C7 121.3(3) . . ?
C10 Fe1 C5A 136.86(14) . . ?
C9 Fe1 C5A 107.54(12) . . ?
C3A Fe1 C5A 68.27(7) . . ?
C4A Fe1 C5A 40.57(6) . . ?
C2A Fe1 C5A 68.16(7) . . ?
C7 Fe1 C5A 139.00(14) . . ?
C10 Fe1 C1A 111.93(12) . . ?
C9 Fe1 C1A 110.82(13) . . ?
C3A Fe1 C1A 68.22(7) . . ?
C4A Fe1 C1A 68.19(7) . . ?
C2A Fe1 C1A 40.50(6) . . ?
C7 Fe1 C1A 179.14(15) . . ?
C5A Fe1 C1A 40.48(6) . . ?
C10 Fe1 C8 68.78(11) . . ?
C9 Fe1 C8 40.78(12) . . ?
C5B Fe1 C8 122.6(3) . . ?
C3A Fe1 C8 136.70(15) . . ?
C4A Fe1 C8 108.14(12) . . ?
C2A Fe1 C8 176.41(11) . . ?
C4B Fe1 C8 105.37(19) . . ?
C7 Fe1 C8 40.61(11) . . ?
C5A Fe1 C8 109.02(12) . . ?
C1A Fe1 C8 138.53(15) . . ?
C10 Fe1 C6 41.59(11) . . ?
C9 Fe1 C6 70.68(12) . . ?
C5B Fe1 C6 160.3(3) . . ?
C3A Fe1 C6 113.52(12) . . ?
C4A Fe1 C6 140.89(14) . . ?
C2A Fe1 C6 113.05(12) . . ?
C4B Fe1 C6 157.0(3) . . ?
C7 Fe1 C6 40.83(11) . . ?
C5A Fe1 C6 178.21(12) . . ?
C1A Fe1 C6 139.66(14) . . ?
C8 Fe1 C6 69.82(11) . . ?
C2A C1A C5A 108.0 . . ?
C2A C1A Fe1 69.56(12) . . ?
C5A C1A Fe1 69.66(12) . . ?
C2A C1A H1A 126.0 . . ?
C5A C1A H1A 126.0 . . ?
Fe1 C1A H1A 126.3 . . ?
C1A C2A C3A 108.0 . . ?
C1A C2A Fe1 69.94(12) . . ?
C3A C2A Fe1 69.48(12) . . ?
C1A C2A H2A 126.0 . . ?
C3A C2A H2A 126.0 . . ?
Fe1 C2A H2A 126.2 . . ?
C4A C3A C2A 108.0 . . ?
C4A C3A Fe1 69.73(12) . . ?
C2A C3A Fe1 69.91(12) . . ?
C4A C3A H3A 126.0 . . ?
C2A C3A H3A 126.0 . . ?
Fe1 C3A H3A 125.9 . . ?
C5A C4A C3A 108.0 . . ?
C5A C4A Fe1 69.96(12) . . ?
C3A C4A Fe1 69.62(12) . . ?
C5A C4A H4A 126.0 . . ?
C3A C4A H4A 126.0 . . ?
Fe1 C4A H4A 126.0 . . ?
C4A C5A C1A 108.0 . . ?
C4A C5A Fe1 69.47(12) . . ?
C1A C5A Fe1 69.86(12) . . ?
C4A C5A H5A 126.0 . . ?
C1A C5A H5A 126.0 . . ?
Fe1 C5A H5A 126.2 . . ?
C5B C1B C2B 108.0 . . ?
C5B C1B Fe1 68.6(3) . . ?
C2B C1B Fe1 71.4(3) . . ?
C5B C1B H1B 126.0 . . ?
C2B C1B H1B 126.0 . . ?
Fe1 C1B H1B 125.6 . . ?
C3B C2B C1B 108.0 . . ?
C3B C2B Fe1 69.9(3) . . ?
C1B C2B Fe1 68.7(3) . . ?
C3B C2B H2B 126.0 . . ?
C1B C2B H2B 126.0 . . ?
Fe1 C2B H2B 127.0 . . ?
C4B C3B C2B 108.0 . . ?
C4B C3B Fe1 68.4(3) . . ?
C2B C3B Fe1 70.5(3) . . ?
C4B C3B H3B 126.0 . . ?
C2B C3B H3B 126.0 . . ?
Fe1 C3B H3B 126.7 . . ?
C3B C4B C5B 108.0 . . ?
C3B C4B Fe1 71.5(3) . . ?
C5B C4B Fe1 69.0(3) . . ?
C3B C4B H4B 126.0 . . ?
C5B C4B H4B 126.0 . . ?
Fe1 C4B H4B 125.1 . . ?
C1B C5B C4B 108.0 . . ?
C1B C5B Fe1 70.8(3) . . ?
C4B C5B Fe1 70.3(3) . . ?
C1B C5B H5B 126.0 . . ?
C4B C5B H5B 126.0 . . ?
Fe1 C5B H5B 124.4 . . ?
C7 C6 C10 103.9(2) . . ?
C7 C6 Si1 124.8(2) . . ?
C10 C6 Si1 131.1(2) . . ?
C7 C6 Fe1 69.21(16) . . ?
C10 C6 Fe1 66.90(15) . . ?
Si1 C6 Fe1 130.89(15) . . ?
C8 C7 C6 111.0(3) . . ?
C8 C7 Fe1 70.03(16) . . ?
C6 C7 Fe1 69.96(16) . . ?
C8 C7 H7 124.5 . . ?
C6 C7 H7 124.5 . . ?
Fe1 C7 H7 127.2 . . ?
C9 C8 C7 107.4(2) . . ?
C9 C8 C17 125.6(3) . . ?
C7 C8 C17 126.9(3) . . ?
C9 C8 Fe1 68.55(16) . . ?
C7 C8 Fe1 69.35(16) . . ?
C17 C8 Fe1 124.3(2) . . ?
C8 C9 C10 106.8(3) . . ?
C8 C9 Fe1 70.67(16) . . ?
C10 C9 Fe1 67.98(15) . . ?
C8 C9 H9 126.6 . . ?
C10 C9 H9 126.6 . . ?
Fe1 C9 H9 126.3 . . ?
C9 C10 C6 110.9(3) . . ?
C9 C10 S1 122.3(2) . . ?
C6 C10 S1 126.7(2) . . ?
C9 C10 Fe1 70.43(16) . . ?
C6 C10 Fe1 71.51(16) . . ?
S1 C10 Fe1 122.44(16) . . ?
C13 Si1 C12 107.34(19) . . ?
C13 Si1 C11 110.74(19) . . ?
C12 Si1 C11 110.84(18) . . ?
C13 Si1 C6 106.04(15) . . ?
C12 Si1 C6 114.54(16) . . ?
C11 Si1 C6 107.25(15) . . ?
Si1 C11 H11A 109.5 . . ?
Si1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
Si1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
Si1 C12 H12A 109.5 . . ?
Si1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
Si1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
Si1 C13 H13A 109.5 . . ?
Si1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
Si1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O14 S1 O15 120.85(18) . . ?
O14 S1 F16 104.50(19) . . ?
O15 S1 F16 104.26(14) . . ?
O14 S1 C10 111.64(15) . . ?
O15 S1 C10 112.20(14) . . ?
F16 S1 C10 100.65(13) . . ?
C22 C17 C18 118.5(3) . . ?
C22 C17 C8 121.4(3) . . ?
C18 C17 C8 120.1(3) . . ?
C19 C18 C17 120.8(3) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 119.6(3) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C21 C20 C19 120.4(3) . . ?
C21 C20 C23 120.4(3) . . ?
C19 C20 C23 119.2(3) . . ?
C20 C21 C22 120.1(3) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C17 120.6(3) . . ?
C21 C22 H22 119.7 . . ?
C17 C22 H22 119.7 . . ?
F25 C23 F26 105.5(4) . . ?
F25 C23 F24 105.6(4) . . ?
F26 C23 F24 104.4(4) . . ?
F25 C23 C20 113.9(3) . . ?
F26 C23 C20 113.0(4) . . ?
F24 C23 C20 113.5(4) . . ?

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
C5A C1A C2A C3A 0.0 . . . . ?
Fe1 C1A C2A C3A -59.27(12) . . . . ?
C5A C1A C2A Fe1 59.27(12) . . . . ?
C1A C2A C3A C4A 0.0 . . . . ?
Fe1 C2A C3A C4A -59.55(12) . . . . ?
C1A C2A C3A Fe1 59.55(12) . . . . ?
C2A C3A C4A C5A 0.0 . . . . ?
Fe1 C3A C4A C5A -59.67(12) . . . . ?
C2A C3A C4A Fe1 59.67(12) . . . . ?
C3A C4A C5A C1A 0.0 . . . . ?
Fe1 C4A C5A C1A -59.45(12) . . . . ?
C3A C4A C5A Fe1 59.45(12) . . . . ?
C2A C1A C5A C4A 0.0 . . . . ?
Fe1 C1A C5A C4A 59.21(12) . . . . ?
C2A C1A C5A Fe1 -59.21(12) . . . . ?
C5B C1B C2B C3B 0.0 . . . . ?
Fe1 C1B C2B C3B -59.0(3) . . . . ?
C5B C1B C2B Fe1 59.0(3) . . . . ?
C1B C2B C3B C4B 0.0 . . . . ?
Fe1 C2B C3B C4B -58.3(3) . . . . ?
C1B C2B C3B Fe1 58.3(3) . . . . ?
C2B C3B C4B C5B 0.0 . . . . ?
Fe1 C3B C4B C5B -59.6(3) . . . . ?
C2B C3B C4B Fe1 59.6(3) . . . . ?
C2B C1B C5B C4B 0.0 . . . . ?
Fe1 C1B C5B C4B 60.8(3) . . . . ?
C2B C1B C5B Fe1 -60.8(3) . . . . ?
C3B C4B C5B C1B 0.0 . . . . ?
Fe1 C4B C5B C1B -61.1(3) . . . . ?
C3B C4B C5B Fe1 61.1(3) . . . . ?
C10 C6 C7 C8 -0.2(3) . . . . ?
Si1 C6 C7 C8 -175.9(2) . . . . ?
Fe1 C6 C7 C8 58.0(2) . . . . ?
C10 C6 C7 Fe1 -58.26(18) . . . . ?
Si1 C6 C7 Fe1 126.1(2) . . . . ?
C6 C7 C8 C9 0.2(3) . . . . ?
Fe1 C7 C8 C9 58.17(19) . . . . ?
C6 C7 C8 C17 -176.0(3) . . . . ?
Fe1 C7 C8 C17 -118.0(3) . . . . ?
C6 C7 C8 Fe1 -58.0(2) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C17 C8 C9 C10 176.2(3) . . . . ?
Fe1 C8 C9 C10 58.62(19) . . . . ?
C7 C8 C9 Fe1 -58.67(19) . . . . ?
C17 C8 C9 Fe1 117.6(3) . . . . ?
C8 C9 C10 C6 -0.1(3) . . . . ?
Fe1 C9 C10 C6 60.2(2) . . . . ?
C8 C9 C10 S1 -177.0(2) . . . . ?
Fe1 C9 C10 S1 -116.7(2) . . . . ?
C8 C9 C10 Fe1 -60.34(19) . . . . ?
C7 C6 C10 C9 0.2(3) . . . . ?
Si1 C6 C10 C9 175.5(2) . . . . ?
Fe1 C6 C10 C9 -59.6(2) . . . . ?
C7 C6 C10 S1 176.9(2) . . . . ?
Si1 C6 C10 S1 -7.8(4) . . . . ?
Fe1 C6 C10 S1 117.1(2) . . . . ?
C7 C6 C10 Fe1 59.81(18) . . . . ?
Si1 C6 C10 Fe1 -124.9(2) . . . . ?
C7 C6 Si1 C13 1.2(3) . . . . ?
C10 C6 Si1 C13 -173.2(3) . . . . ?
Fe1 C6 Si1 C13 93.0(2) . . . . ?
C7 C6 Si1 C12 -116.9(3) . . . . ?
C10 C6 Si1 C12 68.7(3) . . . . ?
Fe1 C6 Si1 C12 -25.2(3) . . . . ?
C7 C6 Si1 C11 119.6(3) . . . . ?
C10 C6 Si1 C11 -54.8(3) . . . . ?
Fe1 C6 Si1 C11 -148.6(2) . . . . ?
C9 C10 S1 O14 17.5(3) . . . . ?
C6 C10 S1 O14 -158.9(3) . . . . ?
Fe1 C10 S1 O14 -68.6(2) . . . . ?
C9 C10 S1 O15 156.8(2) . . . . ?
C6 C10 S1 O15 -19.6(3) . . . . ?
Fe1 C10 S1 O15 70.7(2) . . . . ?
C9 C10 S1 F16 -92.9(3) . . . . ?
C6 C10 S1 F16 90.7(3) . . . . ?
Fe1 C10 S1 F16 -178.98(17) . . . . ?
C9 C8 C17 C22 167.5(3) . . . . ?
C7 C8 C17 C22 -17.0(5) . . . . ?
Fe1 C8 C17 C22 -105.7(3) . . . . ?
C9 C8 C17 C18 -12.8(4) . . . . ?
C7 C8 C17 C18 162.8(3) . . . . ?
Fe1 C8 C17 C18 74.0(3) . . . . ?
C22 C17 C18 C19 0.4(5) . . . . ?
C8 C17 C18 C19 -179.3(3) . . . . ?
C17 C18 C19 C20 -0.4(5) . . . . ?
C18 C19 C20 C21 0.4(5) . . . . ?
C18 C19 C20 C23 177.7(3) . . . . ?
C19 C20 C21 C22 -0.4(6) . . . . ?
C23 C20 C21 C22 -177.7(4) . . . . ?
C20 C21 C22 C17 0.5(6) . . . . ?
C18 C17 C22 C21 -0.5(5) . . . . ?
C8 C17 C22 C21 179.3(3) . . . . ?
C21 C20 C23 F25 90.5(5) . . . . ?
C19 C20 C23 F25 -86.9(5) . . . . ?
C21 C20 C23 F26 -149.1(4) . . . . ?
C19 C20 C23 F26 33.5(5) . . . . ?
C21 C20 C23 F24 -30.4(5) . . . . ?
C19 C20 C23 F24 152.2(4) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


####################################################################### 
# 
# 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_WE13502
_database_code_depnum_ccdc_archive 'CCDC 2189756'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;ISCR
France
;
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2022-09-25 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 08 mars 2021                                             #
#------------------------------------------------------------------------------#


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H19 F Fe I N O2 S Si'
_chemical_formula_sum            'C18 H19 F Fe I N O2 S Si'
_chemical_formula_weight         543.24
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#


_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2515(9)
_cell_length_b                   9.8647(10)
_cell_length_c                   13.6336(15)
_cell_angle_alpha                69.547(3)
_cell_angle_beta                 75.439(4)
_cell_angle_gamma                81.881(3)
_cell_volume                     1004.65(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4057
_cell_measurement_theta_min      2.5552
_cell_measurement_theta_max      27.5052
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      -0.0718014
_diffrn_orient_matrix_UB_21      -0.1017601
_diffrn_orient_matrix_UB_31      0.0150941
_diffrn_orient_matrix_UB_12      -0.0248430
_diffrn_orient_matrix_UB_22      0.0097549
_diffrn_orient_matrix_UB_32      -0.1051059
_diffrn_orient_matrix_UB_13      0.0742401
_diffrn_orient_matrix_UB_23      -0.0297675
_diffrn_orient_matrix_UB_33      0.0068488


#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.796
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             536
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.592
_exptl_absorpt_correction_T_max  0.762

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

# Software                   : BIS V6.2.1/2016-03-01                           #
# Number of scans            :        4                                        #
# Total number of frames [*] :     1104                                        #
# Total length of scans  [*] :   552.00 (deg.)                                 #
# Rotation speed         [*] :    10.00 sec./deg.                              #
# Total exposition time  [*] :      1 h  32.0 min.                             #
#                                                                              #
#  [*] fast scan not included                                                  #
#                                                                              #
# Measurement mode           : shutterless mode                                #
#                                                                              #
#    Scan  Time(s) Width DX(mm) Frames Range  Theta  Omega    Phi    Chi  T(K) #
#..............................................................................#
#                                                                              #
#  1 Phi      5.0  0.50    34.0   720  360.0    0.3  270.9  360.0   23.0 150.0 #
#  2 Omega    5.0  0.50    34.0   192   96.0    0.3    3.2  144.0  315.5 150.0 #
#  3 Omega    5.0  0.50    34.0   192   96.0    0.3    3.2    0.0  315.5 150.0 #
#  4 Fast     1.0  1.00    34.0   180  180.0    0.0  360.0    0.0   54.7 150.0 #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.00
_diffrn_source_voltage           50.00
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0305
_diffrn_reflns_av_r_equivalents  0.0446
_diffrn_reflns_number            4593
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.276
_diffrn_reflns_theta_max         27.514
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_reflns_number_total             4593
_reflns_number_gt                4139
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (G. Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2020)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0240P)²+4.5095P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         4593
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0800
_refine_ls_wR_factor_gt          0.0766
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.681
_refine_diff_density_min         -1.304
_refine_diff_density_rms         0.135

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'
F F 0.0171 0.0103 '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'
I I -0.4742 1.8119 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.36202(6) 0.61702(5) 0.74779(4) 0.01413(11) Uani 1 1 d . . . . .
I1 I 0.67735(3) 0.69942(3) 0.49113(2) 0.01748(7) Uani 1 1 d . . . . .
C1 C 0.2860(9) 0.6241(6) 0.9002(4) 0.0561(18) Uani 1 1 d . . . . .
H1 H 0.216777 0.557293 0.958374 0.067 Uiso 1 1 calc R U . . .
C2 C 0.4590(9) 0.6125(7) 0.8724(5) 0.0544(16) Uani 1 1 d . . . . .
H2 H 0.528783 0.535227 0.907610 0.065 Uiso 1 1 calc R U . . .
C3 C 0.5129(6) 0.7290(7) 0.7868(5) 0.0482(15) Uani 1 1 d . . . . .
H3 H 0.626973 0.746803 0.752799 0.058 Uiso 1 1 calc R U . . .
C4 C 0.3775(8) 0.8180(5) 0.7562(4) 0.0473(14) Uani 1 1 d . . . . .
H4 H 0.381061 0.906891 0.698488 0.057 Uiso 1 1 calc R U . . .
C5 C 0.2306(6) 0.7512(7) 0.8279(5) 0.0499(16) Uani 1 1 d . . . . .
H5 H 0.117504 0.786171 0.826729 0.060 Uiso 1 1 calc R U . . .
C6 C 0.4742(4) 0.5908(4) 0.6029(3) 0.0149(6) Uani 1 1 d . . . . .
C7 C 0.4913(4) 0.4585(4) 0.6875(3) 0.0153(6) Uani 1 1 d . . . . .
H7 H 0.595195 0.408549 0.700163 0.018 Uiso 1 1 calc R U . . .
C8 C 0.3302(4) 0.4115(4) 0.7507(3) 0.0148(6) Uani 1 1 d . . . . .
C9 C 0.2127(4) 0.5216(4) 0.6996(3) 0.0135(6) Uani 1 1 d . . . . .
C10 C 0.2996(4) 0.6327(4) 0.6071(3) 0.0124(6) Uani 1 1 d . . . . .
C11 C 0.2281(4) 0.7512(4) 0.5250(3) 0.0167(7) Uani 1 1 d . . . . .
C12 C 0.2643(5) 0.8941(4) 0.4934(3) 0.0216(7) Uani 1 1 d . . . . .
H12 H 0.336750 0.922017 0.526279 0.026 Uiso 1 1 calc R U . . .
C13 C 0.1952(6) 0.9973(4) 0.4136(3) 0.0295(9) Uani 1 1 d . . . . .
H13 H 0.219571 1.096252 0.390763 0.035 Uiso 1 1 calc R U . . .
C14 C 0.0898(5) 0.9523(5) 0.3683(3) 0.0290(9) Uani 1 1 d . . . . .
H14 H 0.043477 1.022773 0.312934 0.035 Uiso 1 1 calc R U . . .
N15 N 0.0495(4) 0.8150(4) 0.3980(3) 0.0263(7) Uani 1 1 d . . . . .
C16 C 0.1203(5) 0.7173(4) 0.4742(3) 0.0204(7) Uani 1 1 d . . . . .
H16 H 0.095395 0.618732 0.494901 0.025 Uiso 1 1 calc R U . . .
S1 S 0.00025(10) 0.53256(10) 0.75318(7) 0.01806(18) Uani 1 1 d . . . . .
O18 O -0.0371(3) 0.4471(3) 0.8632(2) 0.0289(6) Uani 1 1 d . . . . .
O19 O -0.0702(3) 0.6761(3) 0.7181(2) 0.0268(6) Uani 1 1 d . . . . .
F19 F -0.0688(3) 0.4484(3) 0.6948(2) 0.0295(5) Uani 1 1 d . . . . .
Si1 Si 0.29831(14) 0.22887(11) 0.85970(8) 0.0218(2) Uani 1 1 d . . . . .
C20 C 0.1309(6) 0.1345(5) 0.8421(4) 0.0342(10) Uani 1 1 d . . . . .
H20A H 0.141508 0.151376 0.765606 0.051 Uiso 1 1 calc R U . . .
H20B H 0.020334 0.172607 0.871697 0.051 Uiso 1 1 calc R U . . .
H20C H 0.143405 0.030227 0.879867 0.051 Uiso 1 1 calc R U . . .
C21 C 0.2475(6) 0.2393(5) 0.9983(3) 0.0356(10) Uani 1 1 d . . . . .
H21A H 0.228278 0.142083 1.050492 0.053 Uiso 1 1 calc R U . . .
H21B H 0.146156 0.302710 1.007461 0.053 Uiso 1 1 calc R U . . .
H21C H 0.341278 0.278534 1.009684 0.053 Uiso 1 1 calc R U . . .
C22 C 0.5032(6) 0.1237(5) 0.8374(4) 0.0404(11) Uani 1 1 d . . . . .
H22A H 0.591285 0.170938 0.847936 0.061 Uiso 1 1 calc R U . . .
H22B H 0.531070 0.120089 0.764112 0.061 Uiso 1 1 calc R U . . .
H22C H 0.494715 0.024925 0.888578 0.061 Uiso 1 1 calc R U . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_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 C9 2.001(3) . ?
Fe1 C5 2.032(4) . ?
Fe1 C2 2.036(5) . ?
Fe1 C1 2.037(4) . ?
Fe1 C3 2.045(5) . ?
Fe1 C6 2.048(3) . ?
Fe1 C4 2.049(4) . ?
Fe1 C10 2.058(3) . ?
Fe1 C7 2.060(3) . ?
Fe1 C8 2.066(3) . ?
I1 C6 2.089(3) . ?
C1 C2 1.381(9) . ?
C1 C5 1.398(9) . ?
C1 H1 0.9500 . ?
C2 C3 1.352(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.376(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.428(8) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.425(5) . ?
C6 C10 1.434(4) . ?
C7 C8 1.430(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.455(4) . ?
C8 Si1 1.895(4) . ?
C9 C10 1.452(4) . ?
C9 S1 1.726(3) . ?
C10 C11 1.480(5) . ?
C11 C12 1.375(5) . ?
C11 C16 1.392(5) . ?
C12 C13 1.385(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.380(6) . ?
C13 H13 0.9500 . ?
C14 N15 1.336(5) . ?
C14 H14 0.9500 . ?
N15 C16 1.340(5) . ?
C16 H16 0.9500 . ?
S1 O19 1.416(3) . ?
S1 O18 1.419(3) . ?
S1 F19 1.572(2) . ?
Si1 C21 1.866(4) . ?
Si1 C22 1.869(5) . ?
Si1 C20 1.876(5) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
C9 Fe1 C5 112.20(16) . . ?
C9 Fe1 C2 145.7(2) . . ?
C5 Fe1 C2 67.1(2) . . ?
C9 Fe1 C1 116.6(2) . . ?
C5 Fe1 C1 40.2(3) . . ?
C2 Fe1 C1 39.6(3) . . ?
C9 Fe1 C3 175.4(2) . . ?
C5 Fe1 C3 67.06(19) . . ?
C2 Fe1 C3 38.7(3) . . ?
C1 Fe1 C3 66.0(2) . . ?
C9 Fe1 C6 68.66(13) . . ?
C5 Fe1 C6 147.5(2) . . ?
C2 Fe1 C6 131.5(2) . . ?
C1 Fe1 C6 170.2(2) . . ?
C3 Fe1 C6 109.35(17) . . ?
C9 Fe1 C4 137.3(2) . . ?
C5 Fe1 C4 41.0(2) . . ?
C2 Fe1 C4 66.2(2) . . ?
C1 Fe1 C4 67.3(2) . . ?
C3 Fe1 C4 39.3(2) . . ?
C6 Fe1 C4 115.13(18) . . ?
C9 Fe1 C10 41.88(13) . . ?
C5 Fe1 C10 117.00(19) . . ?
C2 Fe1 C10 171.1(2) . . ?
C1 Fe1 C10 148.4(2) . . ?
C3 Fe1 C10 134.0(2) . . ?
C6 Fe1 C10 40.88(12) . . ?
C4 Fe1 C10 111.12(17) . . ?
C9 Fe1 C7 68.13(13) . . ?
C5 Fe1 C7 171.9(2) . . ?
C2 Fe1 C7 107.76(19) . . ?
C1 Fe1 C7 131.9(2) . . ?
C3 Fe1 C7 113.30(17) . . ?
C6 Fe1 C7 40.60(13) . . ?
C4 Fe1 C7 144.0(2) . . ?
C10 Fe1 C7 69.03(13) . . ?
C9 Fe1 C8 41.88(13) . . ?
C5 Fe1 C8 134.3(2) . . ?
C2 Fe1 C8 112.2(2) . . ?
C1 Fe1 C8 108.44(18) . . ?
C3 Fe1 C8 141.9(2) . . ?
C6 Fe1 C8 69.50(13) . . ?
C4 Fe1 C8 175.16(19) . . ?
C10 Fe1 C8 71.20(13) . . ?
C7 Fe1 C8 40.54(13) . . ?
C2 C1 C5 108.1(5) . . ?
C2 C1 Fe1 70.2(3) . . ?
C5 C1 Fe1 69.7(3) . . ?
C2 C1 H1 126.0 . . ?
C5 C1 H1 126.0 . . ?
Fe1 C1 H1 125.7 . . ?
C3 C2 C1 108.9(5) . . ?
C3 C2 Fe1 71.0(3) . . ?
C1 C2 Fe1 70.2(3) . . ?
C3 C2 H2 125.6 . . ?
C1 C2 H2 125.6 . . ?
Fe1 C2 H2 124.8 . . ?
C2 C3 C4 109.7(5) . . ?
C2 C3 Fe1 70.3(3) . . ?
C4 C3 Fe1 70.5(3) . . ?
C2 C3 H3 125.1 . . ?
C4 C3 H3 125.1 . . ?
Fe1 C3 H3 125.6 . . ?
C3 C4 C5 106.9(5) . . ?
C3 C4 Fe1 70.2(3) . . ?
C5 C4 Fe1 68.9(3) . . ?
C3 C4 H4 126.6 . . ?
C5 C4 H4 126.6 . . ?
Fe1 C4 H4 125.9 . . ?
C1 C5 C4 106.4(5) . . ?
C1 C5 Fe1 70.1(3) . . ?
C4 C5 Fe1 70.1(3) . . ?
C1 C5 H5 126.8 . . ?
C4 C5 H5 126.8 . . ?
Fe1 C5 H5 124.6 . . ?
C7 C6 C10 109.4(3) . . ?
C7 C6 Fe1 70.17(19) . . ?
C10 C6 Fe1 69.95(18) . . ?
C7 C6 I1 123.6(2) . . ?
C10 C6 I1 127.0(2) . . ?
Fe1 C6 I1 127.03(17) . . ?
C6 C7 C8 110.4(3) . . ?
C6 C7 Fe1 69.23(19) . . ?
C8 C7 Fe1 69.96(19) . . ?
C6 C7 H7 124.8 . . ?
C8 C7 H7 124.8 . . ?
Fe1 C7 H7 127.7 . . ?
C7 C8 C9 104.1(3) . . ?
C7 C8 Si1 123.2(2) . . ?
C9 C8 Si1 132.0(3) . . ?
C7 C8 Fe1 69.50(19) . . ?
C9 C8 Fe1 66.64(18) . . ?
Si1 C8 Fe1 134.49(18) . . ?
C10 C9 C8 111.4(3) . . ?
C10 C9 S1 124.0(2) . . ?
C8 C9 S1 124.0(2) . . ?
C10 C9 Fe1 71.18(19) . . ?
C8 C9 Fe1 71.47(19) . . ?
S1 C9 Fe1 117.42(18) . . ?
C6 C10 C9 104.6(3) . . ?
C6 C10 C11 126.3(3) . . ?
C9 C10 C11 128.5(3) . . ?
C6 C10 Fe1 69.17(18) . . ?
C9 C10 Fe1 66.94(18) . . ?
C11 C10 Fe1 134.1(2) . . ?
C12 C11 C16 117.2(3) . . ?
C12 C11 C10 124.0(3) . . ?
C16 C11 C10 118.7(3) . . ?
C11 C12 C13 120.1(4) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 118.1(4) . . ?
C14 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
N15 C14 C13 123.6(4) . . ?
N15 C14 H14 118.2 . . ?
C13 C14 H14 118.2 . . ?
C14 N15 C16 116.9(3) . . ?
N15 C16 C11 124.1(3) . . ?
N15 C16 H16 118.0 . . ?
C11 C16 H16 118.0 . . ?
O19 S1 O18 120.63(18) . . ?
O19 S1 F19 105.08(16) . . ?
O18 S1 F19 104.77(17) . . ?
O19 S1 C9 111.88(16) . . ?
O18 S1 C9 110.89(17) . . ?
F19 S1 C9 101.24(15) . . ?
C21 Si1 C22 109.5(2) . . ?
C21 Si1 C20 109.8(2) . . ?
C22 Si1 C20 108.8(2) . . ?
C21 Si1 C8 113.66(18) . . ?
C22 Si1 C8 104.49(18) . . ?
C20 Si1 C8 110.37(18) . . ?
Si1 C20 H20A 109.5 . . ?
Si1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
Si1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
Si1 C21 H21A 109.5 . . ?
Si1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
Si1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
Si1 C22 H22A 109.5 . . ?
Si1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
Si1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
C5 C1 C2 C3 1.1(6) . . . . ?
Fe1 C1 C2 C3 60.8(3) . . . . ?
C5 C1 C2 Fe1 -59.6(3) . . . . ?
C1 C2 C3 C4 -0.6(6) . . . . ?
Fe1 C2 C3 C4 59.7(3) . . . . ?
C1 C2 C3 Fe1 -60.3(4) . . . . ?
C2 C3 C4 C5 -0.1(5) . . . . ?
Fe1 C3 C4 C5 59.4(3) . . . . ?
C2 C3 C4 Fe1 -59.5(4) . . . . ?
C2 C1 C5 C4 -1.2(5) . . . . ?
Fe1 C1 C5 C4 -61.1(3) . . . . ?
C2 C1 C5 Fe1 59.9(3) . . . . ?
C3 C4 C5 C1 0.8(5) . . . . ?
Fe1 C4 C5 C1 61.1(3) . . . . ?
C3 C4 C5 Fe1 -60.2(3) . . . . ?
C10 C6 C7 C8 -1.3(4) . . . . ?
Fe1 C6 C7 C8 57.8(2) . . . . ?
I1 C6 C7 C8 179.8(2) . . . . ?
C10 C6 C7 Fe1 -59.1(2) . . . . ?
I1 C6 C7 Fe1 121.9(2) . . . . ?
C6 C7 C8 C9 0.6(4) . . . . ?
Fe1 C7 C8 C9 58.0(2) . . . . ?
C6 C7 C8 Si1 172.1(2) . . . . ?
Fe1 C7 C8 Si1 -130.5(3) . . . . ?
C6 C7 C8 Fe1 -57.4(2) . . . . ?
C7 C8 C9 C10 0.3(4) . . . . ?
Si1 C8 C9 C10 -170.1(3) . . . . ?
Fe1 C8 C9 C10 60.2(2) . . . . ?
C7 C8 C9 S1 -171.0(3) . . . . ?
Si1 C8 C9 S1 18.6(5) . . . . ?
Fe1 C8 C9 S1 -111.1(3) . . . . ?
C7 C8 C9 Fe1 -59.9(2) . . . . ?
Si1 C8 C9 Fe1 129.7(3) . . . . ?
C7 C6 C10 C9 1.4(4) . . . . ?
Fe1 C6 C10 C9 -57.8(2) . . . . ?
I1 C6 C10 C9 -179.7(2) . . . . ?
C7 C6 C10 C11 -170.7(3) . . . . ?
Fe1 C6 C10 C11 130.1(3) . . . . ?
I1 C6 C10 C11 8.2(5) . . . . ?
C7 C6 C10 Fe1 59.2(2) . . . . ?
I1 C6 C10 Fe1 -121.8(3) . . . . ?
C8 C9 C10 C6 -1.1(4) . . . . ?
S1 C9 C10 C6 170.2(2) . . . . ?
Fe1 C9 C10 C6 59.3(2) . . . . ?
C8 C9 C10 C11 170.8(3) . . . . ?
S1 C9 C10 C11 -17.9(5) . . . . ?
Fe1 C9 C10 C11 -128.9(3) . . . . ?
C8 C9 C10 Fe1 -60.4(2) . . . . ?
S1 C9 C10 Fe1 110.9(3) . . . . ?
C6 C10 C11 C12 -59.5(5) . . . . ?
C9 C10 C11 C12 130.3(4) . . . . ?
Fe1 C10 C11 C12 36.1(5) . . . . ?
C6 C10 C11 C16 119.0(4) . . . . ?
C9 C10 C11 C16 -51.2(5) . . . . ?
Fe1 C10 C11 C16 -145.5(3) . . . . ?
C16 C11 C12 C13 -0.4(6) . . . . ?
C10 C11 C12 C13 178.1(4) . . . . ?
C11 C12 C13 C14 0.3(6) . . . . ?
C12 C13 C14 N15 0.8(7) . . . . ?
C13 C14 N15 C16 -1.7(6) . . . . ?
C14 N15 C16 C11 1.7(6) . . . . ?
C12 C11 C16 N15 -0.7(6) . . . . ?
C10 C11 C16 N15 -179.2(3) . . . . ?
C10 C9 S1 O19 -17.1(3) . . . . ?
C8 C9 S1 O19 153.1(3) . . . . ?
Fe1 C9 S1 O19 67.8(2) . . . . ?
C10 C9 S1 O18 -154.9(3) . . . . ?
C8 C9 S1 O18 15.3(4) . . . . ?
Fe1 C9 S1 O18 -70.0(2) . . . . ?
C10 C9 S1 F19 94.3(3) . . . . ?
C8 C9 S1 F19 -95.4(3) . . . . ?
Fe1 C9 S1 F19 179.25(17) . . . . ?
C7 C8 Si1 C21 105.9(3) . . . . ?
C9 C8 Si1 C21 -85.1(4) . . . . ?
Fe1 C8 Si1 C21 12.7(3) . . . . ?
C7 C8 Si1 C22 -13.4(4) . . . . ?
C9 C8 Si1 C22 155.6(3) . . . . ?
Fe1 C8 Si1 C22 -106.6(3) . . . . ?
C7 C8 Si1 C20 -130.1(3) . . . . ?
C9 C8 Si1 C20 38.8(4) . . . . ?
Fe1 C8 Si1 C20 136.6(3) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: twin4.res
#...............................................................................


####################################################################### 
# 
# 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_WE18403
_database_code_depnum_ccdc_archive 'CCDC 2189763'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;ISCR
France
;
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2022-09-25 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 07 fevrier 2022                                          #
#------------------------------------------------------------------------------#


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H18 Cl F Fe I N O2 S2'
_chemical_formula_sum            'C19 H18 Cl F Fe I N O2 S2'
_chemical_formula_weight         593.66
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration ad

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   11.0942(5)
_cell_length_b                   11.5718(6)
_cell_length_c                   16.5861(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2129.32(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6838
_cell_measurement_theta_min      2.4559
_cell_measurement_theta_max      27.4838
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      0.0191345
_diffrn_orient_matrix_UB_21      -0.0453536
_diffrn_orient_matrix_UB_31      0.0755092
_diffrn_orient_matrix_UB_12      0.0152479
_diffrn_orient_matrix_UB_22      -0.0711580
_diffrn_orient_matrix_UB_32      -0.0466040
_diffrn_orient_matrix_UB_13      0.0579489
_diffrn_orient_matrix_UB_23      0.0158140
_diffrn_orient_matrix_UB_33      -0.0051861


#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.510
_exptl_crystal_size_min          0.430
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.852
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1168
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.253
_exptl_absorpt_correction_T_max  0.341

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

# Software                   : BIS 2014.5.0.0/23-May-2014 && APEX2_2014.11-0   #
# Number of scans            :        3                                        #
# Total number of frames     :      376                                        #
# Total length of scans      :   188.00 (deg.)                                 #
# Rotation speed             :  ?                                              #
# Total exposition time      :         25.1 min.                               #
#                                                                              #
#    Scan  Time(s) Width DX(mm) Frames Range 2Theta  Omega    Phi    Chi  T(K) #
#..............................................................................#
#                                                                              #
#  1 Omega    4.0  0.50    35.0   189   94.5  344.0  253.7  112.0   24.0 150.0 #
#  2 Omega    4.0  0.50    35.0   187   93.5  344.8  343.2  299.0  -27.7 150.0 #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'APEXII Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 CCD-LDI-APEX2
_diffrn_detector_area_resol_mean 8.33
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_source_current           30.00
_diffrn_source_voltage           50.00
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0280
_diffrn_reflns_av_r_equivalents  0.0183
_diffrn_reflns_number            9677
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.022
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.989
_reflns_number_total             4711
_reflns_number_gt                4557
_reflns_threshold_expression     >2sigma(I)
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_max     0.937
_reflns_Friedel_fraction_full    0.971

_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.
;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2021)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0322P)²+0.2276P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         4711
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0232
_refine_ls_R_factor_gt           0.0218
_refine_ls_wR_factor_ref         0.0538
_refine_ls_wR_factor_gt          0.0531
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.661
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details 
;
Flack x determined using 1863 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.016(8)

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'
Cl Cl 0.1484 0.1585 '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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.8647(4) 0.4108(4) 0.0242(2) 0.0317(9) Uani 1 1 d . . . . .
H1 H 0.882868 0.345863 -0.008730 0.038 Uiso 1 1 calc R U . . .
C2 C 0.9371(4) 0.4556(4) 0.0869(3) 0.0365(11) Uani 1 1 d . . . . .
H2 H 1.013180 0.426431 0.103566 0.044 Uiso 1 1 calc R U . . .
C3 C 0.8762(4) 0.5518(4) 0.1204(2) 0.0361(10) Uani 1 1 d . . . . .
H3 H 0.903814 0.598700 0.163654 0.043 Uiso 1 1 calc R U . . .
C4 C 0.7677(4) 0.5651(4) 0.0782(3) 0.0331(10) Uani 1 1 d . . . . .
H4 H 0.708577 0.622785 0.088077 0.040 Uiso 1 1 calc R U . . .
C5 C 0.7611(4) 0.4797(4) 0.0195(2) 0.0319(10) Uani 1 1 d . . . . .
H5 H 0.696871 0.469672 -0.017727 0.038 Uiso 1 1 calc R U . . .
C6 C 0.6735(3) 0.4068(3) 0.2344(2) 0.0159(7) Uani 1 1 d . . . . .
C7 C 0.6061(3) 0.3543(3) 0.17054(19) 0.0142(7) Uani 1 1 d . . . . .
C8 C 0.6756(3) 0.2593(3) 0.1423(2) 0.0148(7) Uani 1 1 d . . . . .
C9 C 0.7858(3) 0.2535(3) 0.1866(2) 0.0160(7) Uani 1 1 d . . . . .
C10 C 0.7852(3) 0.3470(3) 0.2458(2) 0.0161(7) Uani 1 1 d . . . . .
C11 C 0.4858(3) 0.3892(3) 0.1372(2) 0.0162(7) Uani 1 1 d . . . . .
H11A H 0.471849 0.472095 0.148654 0.019 Uiso 1 1 calc R U . . .
H11B H 0.486309 0.379035 0.077897 0.019 Uiso 1 1 calc R U . . .
N12 N 0.3870(3) 0.3211(3) 0.17176(17) 0.0172(6) Uani 1 1 d . . . . .
C13 C 0.3687(4) 0.3474(4) 0.2572(2) 0.0266(8) Uani 1 1 d . . . . .
H13A H 0.441106 0.326063 0.287665 0.040 Uiso 1 1 calc R U . . .
H13B H 0.299608 0.303442 0.277532 0.040 Uiso 1 1 calc R U . . .
H13C H 0.353301 0.430249 0.263653 0.040 Uiso 1 1 calc R U . . .
C14 C 0.2753(3) 0.3439(4) 0.1272(3) 0.0300(9) Uani 1 1 d . . . . .
H14A H 0.250991 0.424516 0.135403 0.045 Uiso 1 1 calc R U . . .
H14B H 0.211471 0.292505 0.146727 0.045 Uiso 1 1 calc R U . . .
H14C H 0.288686 0.330100 0.069564 0.045 Uiso 1 1 calc R U . . .
O15 O 0.8967(3) 0.1096(4) 0.0924(2) 0.0542(10) Uani 1 1 d . . . . .
O16 O 1.0104(2) 0.1931(3) 0.2039(2) 0.0438(9) Uani 1 1 d . . . . .
F17 F 0.8579(3) 0.0560(2) 0.22717(19) 0.0513(8) Uani 1 1 d . . . . .
C18 C 0.8806(4) 0.2876(3) 0.39332(19) 0.0203(7) Uani 1 1 d . . . . .
C19 C 0.7835(4) 0.2129(4) 0.4018(2) 0.0256(9) Uani 1 1 d . . . . .
H19 H 0.720972 0.212035 0.362655 0.031 Uiso 1 1 calc R U . . .
C20 C 0.7786(5) 0.1389(4) 0.4682(2) 0.0347(11) Uani 1 1 d . . . . .
H20 H 0.712693 0.087090 0.473965 0.042 Uiso 1 1 calc R U . . .
C21 C 0.8687(5) 0.1404(4) 0.5257(2) 0.0382(12) Uani 1 1 d . . . . .
H21 H 0.864514 0.090170 0.570874 0.046 Uiso 1 1 calc R U . . .
C22 C 0.9660(5) 0.2160(4) 0.5172(3) 0.0409(12) Uani 1 1 d . . . . .
H22 H 1.028160 0.217583 0.556579 0.049 Uiso 1 1 calc R U . . .
C23 C 0.9714(4) 0.2884(4) 0.4512(2) 0.0302(10) Uani 1 1 d . . . . .
H23 H 1.037831 0.339424 0.445286 0.036 Uiso 1 1 calc R U . . .
Cl1 Cl 0.62651(9) 0.16460(8) 0.06948(5) 0.02321(19) Uani 1 1 d . . . . .
Fe1 Fe 0.77434(4) 0.40502(4) 0.13138(3) 0.01384(11) Uani 1 1 d . . . . .
I1 I 0.62575(2) 0.55849(2) 0.29457(2) 0.02455(8) Uani 1 1 d . . . . .
S1 S 0.90129(8) 0.15487(8) 0.17030(6) 0.0234(2) Uani 1 1 d . . . . .
S2 S 0.89862(9) 0.38695(9) 0.31328(5) 0.0242(2) Uani 1 1 d . . . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_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
C1 C5 1.401(6) . ?
C1 C2 1.413(7) . ?
C1 Fe1 2.042(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.416(7) . ?
C2 Fe1 2.037(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.401(6) . ?
C3 Fe1 2.048(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(7) . ?
C4 Fe1 2.053(4) . ?
C4 H4 0.9500 . ?
C5 Fe1 2.052(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.432(5) . ?
C6 C10 1.432(5) . ?
C6 Fe1 2.042(3) . ?
C6 I1 2.088(4) . ?
C7 C8 1.422(5) . ?
C7 C11 1.501(5) . ?
C7 Fe1 2.062(3) . ?
C8 C9 1.429(5) . ?
C8 Cl1 1.719(3) . ?
C8 Fe1 2.019(4) . ?
C9 C10 1.461(5) . ?
C9 S1 1.737(4) . ?
C9 Fe1 1.983(4) . ?
C10 S2 1.746(4) . ?
C10 Fe1 2.017(3) . ?
C11 N12 1.467(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
N12 C13 1.464(4) . ?
N12 C14 1.468(5) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
O15 S1 1.395(3) . ?
O16 S1 1.404(3) . ?
F17 S1 1.559(3) . ?
C18 C19 1.389(6) . ?
C18 C23 1.391(5) . ?
C18 S2 1.767(3) . ?
C19 C20 1.397(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.381(7) . ?
C20 H20 0.9500 . ?
C21 C22 1.397(8) . ?
C21 H21 0.9500 . ?
C22 C23 1.378(6) . ?
C22 H22 0.9500 . ?
C23 H23 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
C5 C1 C2 107.3(4) . . ?
C5 C1 Fe1 70.4(2) . . ?
C2 C1 Fe1 69.5(2) . . ?
C5 C1 H1 126.3 . . ?
C2 C1 H1 126.3 . . ?
Fe1 C1 H1 125.4 . . ?
C1 C2 C3 107.8(4) . . ?
C1 C2 Fe1 69.9(2) . . ?
C3 C2 Fe1 70.1(2) . . ?
C1 C2 H2 126.1 . . ?
C3 C2 H2 126.1 . . ?
Fe1 C2 H2 125.4 . . ?
C4 C3 C2 107.5(4) . . ?
C4 C3 Fe1 70.2(2) . . ?
C2 C3 Fe1 69.3(2) . . ?
C4 C3 H3 126.3 . . ?
C2 C3 H3 126.3 . . ?
Fe1 C3 H3 125.8 . . ?
C5 C4 C3 108.5(4) . . ?
C5 C4 Fe1 70.2(2) . . ?
C3 C4 Fe1 69.8(2) . . ?
C5 C4 H4 125.7 . . ?
C3 C4 H4 125.7 . . ?
Fe1 C4 H4 125.8 . . ?
C4 C5 C1 108.8(4) . . ?
C4 C5 Fe1 70.2(2) . . ?
C1 C5 Fe1 69.6(2) . . ?
C4 C5 H5 125.6 . . ?
C1 C5 H5 125.6 . . ?
Fe1 C5 H5 126.2 . . ?
C7 C6 C10 110.1(3) . . ?
C7 C6 Fe1 70.30(19) . . ?
C10 C6 Fe1 68.39(19) . . ?
C7 C6 I1 125.3(3) . . ?
C10 C6 I1 124.3(3) . . ?
Fe1 C6 I1 123.20(18) . . ?
C8 C7 C6 106.8(3) . . ?
C8 C7 C11 124.7(3) . . ?
C6 C7 C11 128.5(3) . . ?
C8 C7 Fe1 68.03(19) . . ?
C6 C7 Fe1 68.86(19) . . ?
C11 C7 Fe1 127.8(2) . . ?
C7 C8 C9 109.3(3) . . ?
C7 C8 Cl1 123.6(3) . . ?
C9 C8 Cl1 127.1(3) . . ?
C7 C8 Fe1 71.2(2) . . ?
C9 C8 Fe1 67.7(2) . . ?
Cl1 C8 Fe1 129.88(19) . . ?
C8 C9 C10 107.9(3) . . ?
C8 C9 S1 125.6(3) . . ?
C10 C9 S1 126.5(3) . . ?
C8 C9 Fe1 70.4(2) . . ?
C10 C9 Fe1 69.82(19) . . ?
S1 C9 Fe1 123.79(19) . . ?
C6 C10 C9 105.9(3) . . ?
C6 C10 S2 125.5(3) . . ?
C9 C10 S2 128.6(3) . . ?
C6 C10 Fe1 70.29(19) . . ?
C9 C10 Fe1 67.35(19) . . ?
S2 C10 Fe1 123.9(2) . . ?
N12 C11 C7 112.0(3) . . ?
N12 C11 H11A 109.2 . . ?
C7 C11 H11A 109.2 . . ?
N12 C11 H11B 109.2 . . ?
C7 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C13 N12 C11 111.7(3) . . ?
C13 N12 C14 109.5(3) . . ?
C11 N12 C14 109.7(3) . . ?
N12 C13 H13A 109.5 . . ?
N12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N12 C14 H14A 109.5 . . ?
N12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C19 C18 C23 119.7(4) . . ?
C19 C18 S2 124.6(3) . . ?
C23 C18 S2 115.7(3) . . ?
C18 C19 C20 119.5(4) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C21 C20 C19 120.5(5) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 119.9(4) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C23 C22 C21 119.6(4) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C22 C23 C18 120.9(4) . . ?
C22 C23 H23 119.6 . . ?
C18 C23 H23 119.6 . . ?
C9 Fe1 C10 42.83(14) . . ?
C9 Fe1 C8 41.83(14) . . ?
C10 Fe1 C8 70.74(14) . . ?
C9 Fe1 C2 111.39(17) . . ?
C10 Fe1 C2 112.56(17) . . ?
C8 Fe1 C2 138.91(18) . . ?
C9 Fe1 C1 113.56(16) . . ?
C10 Fe1 C1 143.20(16) . . ?
C8 Fe1 C1 111.81(16) . . ?
C2 Fe1 C1 40.54(19) . . ?
C9 Fe1 C6 69.97(15) . . ?
C10 Fe1 C6 41.32(15) . . ?
C8 Fe1 C6 68.67(14) . . ?
C2 Fe1 C6 141.80(18) . . ?
C1 Fe1 C6 175.48(16) . . ?
C9 Fe1 C3 137.64(17) . . ?
C10 Fe1 C3 109.06(15) . . ?
C8 Fe1 C3 179.38(18) . . ?
C2 Fe1 C3 40.6(2) . . ?
C1 Fe1 C3 67.98(18) . . ?
C6 Fe1 C3 111.59(16) . . ?
C9 Fe1 C5 142.65(17) . . ?
C10 Fe1 C5 174.49(18) . . ?
C8 Fe1 C5 113.19(16) . . ?
C2 Fe1 C5 67.35(18) . . ?
C1 Fe1 C5 40.02(18) . . ?
C6 Fe1 C5 135.48(17) . . ?
C3 Fe1 C5 67.06(17) . . ?
C9 Fe1 C4 177.32(17) . . ?
C10 Fe1 C4 134.98(17) . . ?
C8 Fe1 C4 140.59(17) . . ?
C2 Fe1 C4 67.47(18) . . ?
C1 Fe1 C4 67.31(18) . . ?
C6 Fe1 C4 109.30(17) . . ?
C3 Fe1 C4 39.96(18) . . ?
C5 Fe1 C4 39.57(19) . . ?
C9 Fe1 C7 70.15(14) . . ?
C10 Fe1 C7 70.29(14) . . ?
C8 Fe1 C7 40.76(14) . . ?
C2 Fe1 C7 177.09(16) . . ?
C1 Fe1 C7 136.71(16) . . ?
C6 Fe1 C7 40.84(13) . . ?
C3 Fe1 C7 139.79(17) . . ?
C5 Fe1 C7 109.88(16) . . ?
C4 Fe1 C7 111.10(16) . . ?
O15 S1 O16 121.1(2) . . ?
O15 S1 F17 105.9(2) . . ?
O16 S1 F17 104.9(2) . . ?
O15 S1 C9 111.36(19) . . ?
O16 S1 C9 111.52(18) . . ?
F17 S1 C9 99.20(16) . . ?
C10 S2 C18 103.17(18) . . ?

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
C5 C1 C2 C3 0.4(5) . . . . ?
Fe1 C1 C2 C3 -60.2(3) . . . . ?
C5 C1 C2 Fe1 60.5(3) . . . . ?
C1 C2 C3 C4 -0.1(5) . . . . ?
Fe1 C2 C3 C4 -60.1(3) . . . . ?
C1 C2 C3 Fe1 60.0(3) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
Fe1 C3 C4 C5 -59.8(3) . . . . ?
C2 C3 C4 Fe1 59.5(3) . . . . ?
C3 C4 C5 C1 0.5(5) . . . . ?
Fe1 C4 C5 C1 -59.1(3) . . . . ?
C3 C4 C5 Fe1 59.5(3) . . . . ?
C2 C1 C5 C4 -0.5(5) . . . . ?
Fe1 C1 C5 C4 59.5(3) . . . . ?
C2 C1 C5 Fe1 -60.0(3) . . . . ?
C10 C6 C7 C8 0.8(4) . . . . ?
Fe1 C6 C7 C8 57.6(2) . . . . ?
I1 C6 C7 C8 174.9(2) . . . . ?
C10 C6 C7 C11 -178.9(3) . . . . ?
Fe1 C6 C7 C11 -122.1(4) . . . . ?
I1 C6 C7 C11 -4.8(5) . . . . ?
C10 C6 C7 Fe1 -56.8(2) . . . . ?
I1 C6 C7 Fe1 117.3(3) . . . . ?
C6 C7 C8 C9 -1.0(4) . . . . ?
C11 C7 C8 C9 178.7(3) . . . . ?
Fe1 C7 C8 C9 57.1(2) . . . . ?
C6 C7 C8 Cl1 175.9(3) . . . . ?
C11 C7 C8 Cl1 -4.4(5) . . . . ?
Fe1 C7 C8 Cl1 -126.0(3) . . . . ?
C6 C7 C8 Fe1 -58.1(2) . . . . ?
C11 C7 C8 Fe1 121.6(3) . . . . ?
C7 C8 C9 C10 0.9(4) . . . . ?
Cl1 C8 C9 C10 -176.0(3) . . . . ?
Fe1 C8 C9 C10 60.1(2) . . . . ?
C7 C8 C9 S1 -177.3(3) . . . . ?
Cl1 C8 C9 S1 5.8(5) . . . . ?
Fe1 C8 C9 S1 -118.1(3) . . . . ?
C7 C8 C9 Fe1 -59.2(2) . . . . ?
Cl1 C8 C9 Fe1 124.0(3) . . . . ?
C7 C6 C10 C9 -0.3(4) . . . . ?
Fe1 C6 C10 C9 -58.2(2) . . . . ?
I1 C6 C10 C9 -174.5(2) . . . . ?
C7 C6 C10 S2 176.1(3) . . . . ?
Fe1 C6 C10 S2 118.2(3) . . . . ?
I1 C6 C10 S2 1.9(4) . . . . ?
C7 C6 C10 Fe1 57.9(2) . . . . ?
I1 C6 C10 Fe1 -116.3(2) . . . . ?
C8 C9 C10 C6 -0.3(4) . . . . ?
S1 C9 C10 C6 177.8(3) . . . . ?
Fe1 C9 C10 C6 60.1(2) . . . . ?
C8 C9 C10 S2 -176.6(3) . . . . ?
S1 C9 C10 S2 1.6(5) . . . . ?
Fe1 C9 C10 S2 -116.1(3) . . . . ?
C8 C9 C10 Fe1 -60.4(2) . . . . ?
S1 C9 C10 Fe1 117.7(3) . . . . ?
C8 C7 C11 N12 82.8(4) . . . . ?
C6 C7 C11 N12 -97.6(4) . . . . ?
Fe1 C7 C11 N12 170.5(2) . . . . ?
C7 C11 N12 C13 68.4(4) . . . . ?
C7 C11 N12 C14 -170.0(3) . . . . ?
C23 C18 C19 C20 -0.3(6) . . . . ?
S2 C18 C19 C20 -179.3(3) . . . . ?
C18 C19 C20 C21 0.6(6) . . . . ?
C19 C20 C21 C22 -0.4(6) . . . . ?
C20 C21 C22 C23 -0.2(7) . . . . ?
C21 C22 C23 C18 0.4(7) . . . . ?
C19 C18 C23 C22 -0.2(6) . . . . ?
S2 C18 C23 C22 178.9(3) . . . . ?
C8 C9 S1 O15 22.0(4) . . . . ?
C10 C9 S1 O15 -155.9(3) . . . . ?
Fe1 C9 S1 O15 -67.1(3) . . . . ?
C8 C9 S1 O16 160.6(3) . . . . ?
C10 C9 S1 O16 -17.2(4) . . . . ?
Fe1 C9 S1 O16 71.6(3) . . . . ?
C8 C9 S1 F17 -89.2(3) . . . . ?
C10 C9 S1 F17 92.9(3) . . . . ?
Fe1 C9 S1 F17 -178.3(2) . . . . ?
C6 C10 S2 C18 103.4(3) . . . . ?
C9 C10 S2 C18 -81.0(3) . . . . ?
Fe1 C10 S2 C18 -167.7(2) . . . . ?
C19 C18 S2 C10 -10.0(4) . . . . ?
C23 C18 S2 C10 170.9(3) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


####################################################################### 
# 
# 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_WE18261
_database_code_depnum_ccdc_archive 'CCDC 2189761'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;ISCR
France
;
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2022-09-25 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 07 fevrier 2022                                          #
#------------------------------------------------------------------------------#


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H14 Cl F Fe O4 S2'
_chemical_formula_sum            'C18 H14 Cl F Fe O4 S2'
_chemical_formula_weight         468.71
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.4412(13)
_cell_length_b                   17.6060(14)
_cell_length_c                   8.5001(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.985(4)
_cell_angle_gamma                90
_cell_volume                     1843.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4176
_cell_measurement_theta_min      2.6821
_cell_measurement_theta_max      27.4111
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      0.1169376
_diffrn_orient_matrix_UB_21      0.0161244
_diffrn_orient_matrix_UB_31      -0.0133589
_diffrn_orient_matrix_UB_12      -0.0052435
_diffrn_orient_matrix_UB_22      -0.0083198
_diffrn_orient_matrix_UB_32      -0.0559409
_diffrn_orient_matrix_UB_13      -0.0009706
_diffrn_orient_matrix_UB_23      0.0802894
_diffrn_orient_matrix_UB_33      -0.0118500


#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.210
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             952
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.703
_exptl_absorpt_correction_T_max  0.774

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

# Software                   : BIS 2014.5.0.0/23-May-2014 && APEX2_2014.11-0   #
# Number of scans            :        3                                        #
# Total number of frames     :      274                                        #
# Total length of scans      :   274.00 (deg.)                                 #
# Rotation speed             :    10.00 sec./deg.                              #
# Total exposition time      :         45.7 min.                               #
#                                                                              #
#    Scan  Time(s) Width DX(mm) Frames Range 2Theta  Omega    Phi    Chi  T(K) #
#..............................................................................#
#                                                                              #
#  1 Omega   10.0  1.00    35.0   106  106.0   16.0   14.6  262.9  -53.1 150.0 #
#  2 Omega   10.0  1.00    35.0    72   72.0  344.0  342.8  333.7  -55.7 150.0 #
#  3 Omega   10.0  1.00    35.0    96   96.0  344.0  251.2  277.6   29.5 150.0 #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'APEXII Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 CCD-LDI-APEX2
_diffrn_detector_area_resol_mean 8.33
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_source_current           30.00
_diffrn_source_voltage           50.00
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0393
_diffrn_reflns_av_r_equivalents  0.0284
_diffrn_reflns_number            11624
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.682
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.986
_reflns_number_total             4157
_reflns_number_gt                3318
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2021)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0319P)²+0.8644P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         4157
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0767
_refine_ls_wR_factor_gt          0.0713
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.071

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'
Cl Cl 0.1484 0.1585 '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'
Fe Fe 0.3463 0.8444 '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'

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 0.76204(3) 0.59113(2) 0.55971(4) 0.01626(9) Uani 1 1 d . . . . .
Cl1 Cl 0.58631(5) 0.67667(3) 0.27397(6) 0.02391(14) Uani 1 1 d . . . . .
C1 C 0.8722(2) 0.59114(14) 0.7633(3) 0.0286(6) Uani 1 1 d . . . . .
H1 H 0.880044 0.552565 0.842197 0.034 Uiso 1 1 calc R U . . .
C2 C 0.9271(2) 0.59422(14) 0.6277(3) 0.0305(6) Uani 1 1 d . . . . .
H2 H 0.978116 0.558208 0.599909 0.037 Uiso 1 1 calc R U . . .
C3 C 0.8920(2) 0.66076(14) 0.5412(3) 0.0324(6) Uani 1 1 d . . . . .
H3 H 0.915300 0.677198 0.444947 0.039 Uiso 1 1 calc R U . . .
C4 C 0.8163(2) 0.69818(13) 0.6236(3) 0.0307(6) Uani 1 1 d . . . . .
H4 H 0.779771 0.744288 0.592309 0.037 Uiso 1 1 calc R U . . .
C5 C 0.8042(2) 0.65527(14) 0.7604(3) 0.0295(6) Uani 1 1 d . . . . .
H5 H 0.758241 0.667500 0.837186 0.035 Uiso 1 1 calc R U . . .
C6 C 0.63317(18) 0.60029(11) 0.3903(2) 0.0175(5) Uani 1 1 d . . . . .
C7 C 0.59821(18) 0.57779(12) 0.5373(2) 0.0173(5) Uani 1 1 d . . . . .
C8 C 0.65079(18) 0.50728(12) 0.5851(3) 0.0179(5) Uani 1 1 d . . . . .
H8 H 0.642541 0.479994 0.679134 0.022 Uiso 1 1 calc R U . . .
C9 C 0.71712(18) 0.48461(12) 0.4701(2) 0.0173(5) Uani 1 1 d . . . . .
C10 C 0.70696(18) 0.54298(12) 0.3493(2) 0.0171(5) Uani 1 1 d . . . . .
C11 C 0.53041(18) 0.62349(12) 0.6309(3) 0.0185(5) Uani 1 1 d . . . . .
O12 O 0.49342(13) 0.68535(9) 0.59292(19) 0.0248(4) Uani 1 1 d . . . . .
O13 O 0.51497(13) 0.58751(9) 0.76481(18) 0.0240(4) Uani 1 1 d . . . . .
C14 C 0.4549(2) 0.63041(14) 0.8698(3) 0.0301(6) Uani 1 1 d . . . . .
H14A H 0.493368 0.677872 0.900535 0.045 Uiso 1 1 calc R U . . .
H14B H 0.448611 0.600300 0.965073 0.045 Uiso 1 1 calc R U . . .
H14C H 0.382275 0.642011 0.814701 0.045 Uiso 1 1 calc R U . . .
S1 S 0.77406(5) 0.54567(3) 0.18400(6) 0.02105(14) Uani 1 1 d . . . . .
F15 F 0.68164(14) 0.51966(10) 0.05272(16) 0.0485(4) Uani 1 1 d . . . . .
O16 O 0.85369(16) 0.48889(11) 0.1927(2) 0.0427(5) Uani 1 1 d . . . . .
O17 O 0.79874(17) 0.62033(10) 0.1423(2) 0.0396(5) Uani 1 1 d . . . . .
S2 S 0.79264(5) 0.40002(3) 0.46545(7) 0.02118(14) Uani 1 1 d . . . . .
C18 C 0.80139(18) 0.36952(12) 0.6673(3) 0.0180(5) Uani 1 1 d . . . . .
C19 C 0.71747(19) 0.33028(12) 0.7213(3) 0.0207(5) Uani 1 1 d . . . . .
H19 H 0.651744 0.321697 0.652283 0.025 Uiso 1 1 calc R U . . .
C20 C 0.7291(2) 0.30338(13) 0.8763(3) 0.0256(5) Uani 1 1 d . . . . .
H20 H 0.671049 0.276957 0.913748 0.031 Uiso 1 1 calc R U . . .
C21 C 0.8256(2) 0.31518(14) 0.9765(3) 0.0324(6) Uani 1 1 d . . . . .
H21 H 0.833378 0.297294 1.082943 0.039 Uiso 1 1 calc R U . . .
C22 C 0.9105(2) 0.35291(14) 0.9217(3) 0.0356(7) Uani 1 1 d . . . . .
H22 H 0.977024 0.359969 0.989770 0.043 Uiso 1 1 calc R U . . .
C23 C 0.8986(2) 0.38053(13) 0.7672(3) 0.0273(5) Uani 1 1 d . . . . .
H23 H 0.956706 0.406872 0.729812 0.033 Uiso 1 1 calc R U . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_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 C6 2.007(2) . ?
Fe1 C10 2.012(2) . ?
Fe1 C7 2.034(2) . ?
Fe1 C4 2.049(2) . ?
Fe1 C3 2.053(2) . ?
Fe1 C5 2.053(2) . ?
Fe1 C1 2.053(2) . ?
Fe1 C8 2.055(2) . ?
Fe1 C2 2.055(2) . ?
Fe1 C9 2.072(2) . ?
Cl1 C6 1.722(2) . ?
C1 C5 1.409(3) . ?
C1 C2 1.419(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.420(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.413(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.413(4) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.434(3) . ?
C6 C10 1.439(3) . ?
C7 C8 1.435(3) . ?
C7 C11 1.476(3) . ?
C8 C9 1.421(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.446(3) . ?
C9 S2 1.764(2) . ?
C10 S1 1.732(2) . ?
C11 O12 1.209(3) . ?
C11 O13 1.339(3) . ?
O13 C14 1.453(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
S1 O16 1.4021(18) . ?
S1 O17 1.4065(17) . ?
S1 F15 1.5558(16) . ?
S2 C18 1.786(2) . ?
C18 C19 1.383(3) . ?
C18 C23 1.391(3) . ?
C19 C20 1.389(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.388(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.382(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.389(3) . ?
C22 H22 0.9500 . ?
C23 H23 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
C6 Fe1 C10 41.97(8) . . ?
C6 Fe1 C7 41.57(9) . . ?
C10 Fe1 C7 69.81(9) . . ?
C6 Fe1 C4 108.48(9) . . ?
C10 Fe1 C4 132.99(10) . . ?
C7 Fe1 C4 114.83(10) . . ?
C6 Fe1 C3 117.15(10) . . ?
C10 Fe1 C3 110.98(10) . . ?
C7 Fe1 C3 148.38(10) . . ?
C4 Fe1 C3 40.28(11) . . ?
C6 Fe1 C5 129.69(10) . . ?
C10 Fe1 C5 170.79(9) . . ?
C7 Fe1 C5 106.17(10) . . ?
C4 Fe1 C5 40.29(10) . . ?
C3 Fe1 C5 67.80(11) . . ?
C6 Fe1 C1 167.97(10) . . ?
C10 Fe1 C1 148.71(10) . . ?
C7 Fe1 C1 128.47(10) . . ?
C4 Fe1 C1 67.66(10) . . ?
C3 Fe1 C1 67.90(10) . . ?
C5 Fe1 C1 40.15(10) . . ?
C6 Fe1 C8 69.55(9) . . ?
C10 Fe1 C8 68.88(9) . . ?
C7 Fe1 C8 41.09(8) . . ?
C4 Fe1 C8 146.56(10) . . ?
C3 Fe1 C8 170.46(10) . . ?
C5 Fe1 C8 113.94(10) . . ?
C1 Fe1 C8 106.98(9) . . ?
C6 Fe1 C2 150.12(10) . . ?
C10 Fe1 C2 117.70(10) . . ?
C7 Fe1 C2 168.06(10) . . ?
C4 Fe1 C2 67.78(10) . . ?
C3 Fe1 C2 40.43(10) . . ?
C5 Fe1 C2 67.77(10) . . ?
C1 Fe1 C2 40.43(10) . . ?
C8 Fe1 C2 130.58(10) . . ?
C6 Fe1 C9 70.20(8) . . ?
C10 Fe1 C9 41.45(8) . . ?
C7 Fe1 C9 69.23(8) . . ?
C4 Fe1 C9 172.74(10) . . ?
C3 Fe1 C9 133.44(10) . . ?
C5 Fe1 C9 145.94(9) . . ?
C1 Fe1 C9 115.11(9) . . ?
C8 Fe1 C9 40.29(8) . . ?
C2 Fe1 C9 109.59(9) . . ?
C5 C1 C2 108.1(2) . . ?
C5 C1 Fe1 69.91(13) . . ?
C2 C1 Fe1 69.87(14) . . ?
C5 C1 H1 125.9 . . ?
C2 C1 H1 125.9 . . ?
Fe1 C1 H1 125.9 . . ?
C3 C2 C1 107.7(2) . . ?
C3 C2 Fe1 69.68(14) . . ?
C1 C2 Fe1 69.70(14) . . ?
C3 C2 H2 126.1 . . ?
C1 C2 H2 126.1 . . ?
Fe1 C2 H2 126.0 . . ?
C4 C3 C2 107.8(2) . . ?
C4 C3 Fe1 69.74(14) . . ?
C2 C3 Fe1 69.88(14) . . ?
C4 C3 H3 126.1 . . ?
C2 C3 H3 126.1 . . ?
Fe1 C3 H3 125.9 . . ?
C3 C4 C5 108.3(2) . . ?
C3 C4 Fe1 69.97(13) . . ?
C5 C4 Fe1 69.97(13) . . ?
C3 C4 H4 125.9 . . ?
C5 C4 H4 125.9 . . ?
Fe1 C4 H4 125.8 . . ?
C1 C5 C4 108.1(2) . . ?
C1 C5 Fe1 69.94(13) . . ?
C4 C5 Fe1 69.74(13) . . ?
C1 C5 H5 126.0 . . ?
C4 C5 H5 126.0 . . ?
Fe1 C5 H5 125.9 . . ?
C7 C6 C10 107.36(18) . . ?
C7 C6 Cl1 126.61(17) . . ?
C10 C6 Cl1 125.77(17) . . ?
C7 C6 Fe1 70.23(12) . . ?
C10 C6 Fe1 69.19(12) . . ?
Cl1 C6 Fe1 130.36(12) . . ?
C8 C7 C6 107.71(19) . . ?
C8 C7 C11 126.2(2) . . ?
C6 C7 C11 125.75(19) . . ?
C8 C7 Fe1 70.25(12) . . ?
C6 C7 Fe1 68.20(13) . . ?
C11 C7 Fe1 121.78(15) . . ?
C9 C8 C7 109.46(19) . . ?
C9 C8 Fe1 70.47(12) . . ?
C7 C8 Fe1 68.66(12) . . ?
C9 C8 H8 125.3 . . ?
C7 C8 H8 125.3 . . ?
Fe1 C8 H8 127.2 . . ?
C8 C9 C10 106.69(18) . . ?
C8 C9 S2 127.91(16) . . ?
C10 C9 S2 125.33(16) . . ?
C8 C9 Fe1 69.24(12) . . ?
C10 C9 Fe1 67.06(11) . . ?
S2 C9 Fe1 130.93(12) . . ?
C6 C10 C9 108.77(18) . . ?
C6 C10 S1 124.98(16) . . ?
C9 C10 S1 126.24(16) . . ?
C6 C10 Fe1 68.84(12) . . ?
C9 C10 Fe1 71.49(12) . . ?
S1 C10 Fe1 124.53(12) . . ?
O12 C11 O13 124.0(2) . . ?
O12 C11 C7 124.9(2) . . ?
O13 C11 C7 111.14(18) . . ?
C11 O13 C14 115.01(17) . . ?
O13 C14 H14A 109.5 . . ?
O13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O16 S1 O17 120.15(12) . . ?
O16 S1 F15 105.93(12) . . ?
O17 S1 F15 105.05(11) . . ?
O16 S1 C10 110.75(10) . . ?
O17 S1 C10 112.13(10) . . ?
F15 S1 C10 100.51(10) . . ?
C9 S2 C18 101.17(10) . . ?
C19 C18 C23 119.9(2) . . ?
C19 C18 S2 121.41(17) . . ?
C23 C18 S2 118.43(18) . . ?
C18 C19 C20 120.1(2) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C21 119.9(2) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C22 C21 C20 120.1(2) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C23 120.1(2) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C22 C23 C18 119.9(2) . . ?
C22 C23 H23 120.1 . . ?
C18 C23 H23 120.1 . . ?

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
C5 C1 C2 C3 -0.1(3) . . . . ?
Fe1 C1 C2 C3 59.55(16) . . . . ?
C5 C1 C2 Fe1 -59.68(16) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
Fe1 C2 C3 C4 59.66(17) . . . . ?
C1 C2 C3 Fe1 -59.56(16) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
Fe1 C3 C4 C5 59.72(17) . . . . ?
C2 C3 C4 Fe1 -59.75(17) . . . . ?
C2 C1 C5 C4 0.1(3) . . . . ?
Fe1 C1 C5 C4 -59.54(17) . . . . ?
C2 C1 C5 Fe1 59.65(16) . . . . ?
C3 C4 C5 C1 0.0(3) . . . . ?
Fe1 C4 C5 C1 59.67(17) . . . . ?
C3 C4 C5 Fe1 -59.72(17) . . . . ?
C10 C6 C7 C8 0.1(2) . . . . ?
Cl1 C6 C7 C8 174.48(16) . . . . ?
Fe1 C6 C7 C8 -59.34(15) . . . . ?
C10 C6 C7 C11 173.74(19) . . . . ?
Cl1 C6 C7 C11 -11.9(3) . . . . ?
Fe1 C6 C7 C11 114.3(2) . . . . ?
C10 C6 C7 Fe1 59.48(15) . . . . ?
Cl1 C6 C7 Fe1 -126.18(18) . . . . ?
C6 C7 C8 C9 -0.7(2) . . . . ?
C11 C7 C8 C9 -174.3(2) . . . . ?
Fe1 C7 C8 C9 -58.75(15) . . . . ?
C6 C7 C8 Fe1 58.07(15) . . . . ?
C11 C7 C8 Fe1 -115.5(2) . . . . ?
C7 C8 C9 C10 0.9(2) . . . . ?
Fe1 C8 C9 C10 -56.72(14) . . . . ?
C7 C8 C9 S2 -175.97(16) . . . . ?
Fe1 C8 C9 S2 126.36(18) . . . . ?
C7 C8 C9 Fe1 57.66(15) . . . . ?
C7 C6 C10 C9 0.5(2) . . . . ?
Cl1 C6 C10 C9 -173.95(16) . . . . ?
Fe1 C6 C10 C9 60.59(15) . . . . ?
C7 C6 C10 S1 -178.23(16) . . . . ?
Cl1 C6 C10 S1 7.4(3) . . . . ?
Fe1 C6 C10 S1 -118.10(17) . . . . ?
C7 C6 C10 Fe1 -60.14(15) . . . . ?
Cl1 C6 C10 Fe1 125.46(18) . . . . ?
C8 C9 C10 C6 -0.9(2) . . . . ?
S2 C9 C10 C6 176.16(15) . . . . ?
Fe1 C9 C10 C6 -58.95(14) . . . . ?
C8 C9 C10 S1 177.81(16) . . . . ?
S2 C9 C10 S1 -5.2(3) . . . . ?
Fe1 C9 C10 S1 119.72(18) . . . . ?
C8 C9 C10 Fe1 58.09(15) . . . . ?
S2 C9 C10 Fe1 -124.89(17) . . . . ?
C8 C7 C11 O12 174.4(2) . . . . ?
C6 C7 C11 O12 1.9(4) . . . . ?
Fe1 C7 C11 O12 86.6(2) . . . . ?
C8 C7 C11 O13 -5.5(3) . . . . ?
C6 C7 C11 O13 -178.0(2) . . . . ?
Fe1 C7 C11 O13 -93.3(2) . . . . ?
O12 C11 O13 C14 -3.7(3) . . . . ?
C7 C11 O13 C14 176.17(18) . . . . ?
C6 C10 S1 O16 169.60(19) . . . . ?
C9 C10 S1 O16 -8.9(2) . . . . ?
Fe1 C10 S1 O16 82.66(16) . . . . ?
C6 C10 S1 O17 32.4(2) . . . . ?
C9 C10 S1 O17 -146.08(19) . . . . ?
Fe1 C10 S1 O17 -54.55(17) . . . . ?
C6 C10 S1 F15 -78.8(2) . . . . ?
C9 C10 S1 F15 102.8(2) . . . . ?
Fe1 C10 S1 F15 -165.69(13) . . . . ?
C8 C9 S2 C18 -19.1(2) . . . . ?
C10 C9 S2 C18 164.51(19) . . . . ?
Fe1 C9 S2 C18 75.53(16) . . . . ?
C9 S2 C18 C19 82.05(19) . . . . ?
C9 S2 C18 C23 -103.19(19) . . . . ?
C23 C18 C19 C20 1.5(3) . . . . ?
S2 C18 C19 C20 176.20(17) . . . . ?
C18 C19 C20 C21 -0.8(3) . . . . ?
C19 C20 C21 C22 -0.7(4) . . . . ?
C20 C21 C22 C23 1.3(4) . . . . ?
C21 C22 C23 C18 -0.6(4) . . . . ?
C19 C18 C23 C22 -0.9(4) . . . . ?
S2 C18 C23 C22 -175.7(2) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


####################################################################### 
# 
# 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_WE13061
_database_code_depnum_ccdc_archive 'CCDC 2189765'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;ISCR
France
;
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2022-09-25 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 05 fevrier 2021                                          #
#------------------------------------------------------------------------------#


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H11 F Fe O2 S2'
_chemical_formula_sum            'C14 H11 F Fe O2 S2'
_chemical_formula_weight         350.20
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#


_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.9750(11)
_cell_length_b                   21.685(4)
_cell_length_c                   7.7176(12)
_cell_angle_alpha                90
_cell_angle_beta                 93.869(5)
_cell_angle_gamma                90
_cell_volume                     1331.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9789
_cell_measurement_theta_min      2.8179
_cell_measurement_theta_max      27.4940
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      -0.1220856
_diffrn_orient_matrix_UB_21      0.0419586
_diffrn_orient_matrix_UB_31      -0.0141762
_diffrn_orient_matrix_UB_12      0.0140163
_diffrn_orient_matrix_UB_22      0.0432971
_diffrn_orient_matrix_UB_32      0.0074422
_diffrn_orient_matrix_UB_13      0.0114168
_diffrn_orient_matrix_UB_23      0.0176036
_diffrn_orient_matrix_UB_33      -0.1239146


#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.110
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.747
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             712
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.453
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.746
_exptl_absorpt_correction_T_max  0.852

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

# Software                   : BIS V6.2.1/2016-03-01                           #
# Number of scans            :        3                                        #
# Total number of frames [*] :      250                                        #
# Total length of scans  [*] :   250.00 (deg.)                                 #
# Rotation speed         [*] :     8.00 sec./deg.                              #
# Total exposition time  [*] :         33.3 min.                               #
#                                                                              #
#  [*] fast scan not included                                                  #
#                                                                              #
# Measurement mode           : shutterless mode                                #
#                                                                              #
#    Scan  Time(s)  Width  DX (mm)  Frames  Theta  Omega    Phi    Chi   T(K)  #
#..............................................................................#
#                                                                              #
#  1 Phi       8.0   1.00     34.0     192   0.27 270.94 252.00  23.00 150.00  #
#  2 Omega     8.0   1.00     34.0      58   0.63 303.10  45.34  57.37 150.00  #
#  3 Fast      1.0   1.00     50.0     180   0.00 360.00   0.00  54.74 150.00  #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.00
_diffrn_source_voltage           50.00
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0318
_diffrn_reflns_av_r_equivalents  0.0360
_diffrn_reflns_number            13235
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.727
_diffrn_reflns_theta_max         27.505
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_reflns_number_total             3038
_reflns_number_gt                2676
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2020)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0375P)²+3.1460P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         3038
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0775
_refine_ls_wR_factor_gt          0.0723
_refine_ls_goodness_of_fit_ref   0.834
_refine_ls_restrained_S_all      0.834
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.076

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'
F F 0.0171 0.0103 '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'
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'

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
C1 C 0.5457(3) 0.67300(12) 0.9750(3) 0.0324(6) Uani 1 1 d . . . . .
H1 H 0.642384 0.663786 1.049224 0.039 Uiso 1 1 calc R U . . .
C2 C 0.5354(3) 0.71762(10) 0.8421(3) 0.0251(5) Uani 1 1 d . . . . .
H2 H 0.624025 0.743904 0.811497 0.030 Uiso 1 1 calc R U . . .
C3 C 0.3707(3) 0.71660(10) 0.7622(3) 0.0235(4) Uani 1 1 d . . . . .
H3 H 0.329573 0.741917 0.668229 0.028 Uiso 1 1 calc R U . . .
C4 C 0.2774(3) 0.67126(11) 0.8465(3) 0.0273(5) Uani 1 1 d . . . . .
H4 H 0.162870 0.660936 0.819170 0.033 Uiso 1 1 calc R U . . .
C5 C 0.3850(4) 0.64404(11) 0.9786(3) 0.0337(6) Uani 1 1 d . . . . .
H5 H 0.355682 0.612260 1.055678 0.040 Uiso 1 1 calc R U . . .
C6 C 0.4675(3) 0.60691(11) 0.4834(3) 0.0194(4) Uani 1 1 d . . . . .
H6 H 0.426217 0.631175 0.387300 0.023 Uiso 1 1 calc R U . . .
C7 C 0.3693(3) 0.56560(11) 0.5787(3) 0.0226(4) Uani 1 1 d . . . . .
H7 H 0.252483 0.557977 0.556894 0.027 Uiso 1 1 calc R U . . .
C8 C 0.4754(3) 0.53781(10) 0.7116(3) 0.0195(4) Uani 1 1 d . . . . .
H8 H 0.443399 0.508182 0.793844 0.023 Uiso 1 1 calc R U . . .
C9 C 0.6408(2) 0.56317(9) 0.6978(3) 0.0152(4) Uani 1 1 d . . . . .
C10 C 0.6375(2) 0.60617(9) 0.5548(2) 0.0144(4) Uani 1 1 d . . . . .
C11 C 0.7823(2) 0.63680(9) 0.4814(3) 0.0148(4) Uani 1 1 d . . . . .
C12 C 0.8493(3) 0.61550(10) 0.3342(3) 0.0218(4) Uani 1 1 d . . . . .
H12 H 0.808810 0.580342 0.270993 0.026 Uiso 1 1 calc R U . . .
C13 C 0.8688(3) 0.69018(11) 0.5482(3) 0.0227(4) Uani 1 1 d . . . . .
H13 H 0.840563 0.711326 0.650044 0.027 Uiso 1 1 calc R U . . .
C14 C 0.9988(3) 0.70783(11) 0.4479(3) 0.0225(4) Uani 1 1 d . . . . .
H14 H 1.069481 0.742457 0.472140 0.027 Uiso 1 1 calc R U . . .
O15 O 0.7603(2) 0.51055(9) 0.9791(2) 0.0359(4) Uani 1 1 d . . . . .
O16 O 0.9196(2) 0.59714(8) 0.8689(2) 0.0297(4) Uani 1 1 d . . . . .
F17 F 0.9088(2) 0.50098(8) 0.7241(2) 0.0430(4) Uani 1 1 d . . . . .
Fe1 Fe 0.47877(3) 0.63109(2) 0.74265(4) 0.01358(9) Uani 1 1 d . . . . .
S1 S 1.01533(7) 0.65987(3) 0.27721(8) 0.02970(15) Uani 1 1 d . . . . .
S2 S 0.81082(6) 0.54618(2) 0.83835(7) 0.01832(12) Uani 1 1 d . . . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_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
C1 C2 1.408(4) . ?
C1 C5 1.429(4) . ?
C1 Fe1 2.049(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.414(3) . ?
C2 Fe1 2.066(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.417(3) . ?
C3 Fe1 2.055(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.417(4) . ?
C4 Fe1 2.038(2) . ?
C4 H4 0.9500 . ?
C5 Fe1 2.034(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.426(3) . ?
C6 C10 1.428(3) . ?
C6 Fe1 2.064(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.419(3) . ?
C7 Fe1 2.057(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.440(3) . ?
C8 Fe1 2.037(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.444(3) . ?
C9 S2 1.718(2) . ?
C9 Fe1 2.005(2) . ?
C10 C11 1.478(3) . ?
C10 Fe1 2.0601(19) . ?
C11 C12 1.368(3) . ?
C11 C13 1.426(3) . ?
C12 S1 1.718(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(3) . ?
C13 H13 0.9500 . ?
C14 S1 1.690(2) . ?
C14 H14 0.9500 . ?
O15 S2 1.4139(17) . ?
O16 S2 1.4149(17) . ?
F17 S2 1.5626(15) . ?

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
C2 C1 C5 107.9(2) . . ?
C2 C1 Fe1 70.63(13) . . ?
C5 C1 Fe1 68.95(13) . . ?
C2 C1 H1 126.0 . . ?
C5 C1 H1 126.0 . . ?
Fe1 C1 H1 125.9 . . ?
C1 C2 C3 108.3(2) . . ?
C1 C2 Fe1 69.34(13) . . ?
C3 C2 Fe1 69.51(12) . . ?
C1 C2 H2 125.9 . . ?
C3 C2 H2 125.9 . . ?
Fe1 C2 H2 126.9 . . ?
C2 C3 C4 108.2(2) . . ?
C2 C3 Fe1 70.36(13) . . ?
C4 C3 Fe1 69.11(13) . . ?
C2 C3 H3 125.9 . . ?
C4 C3 H3 125.9 . . ?
Fe1 C3 H3 126.2 . . ?
C5 C4 C3 107.9(2) . . ?
C5 C4 Fe1 69.49(13) . . ?
C3 C4 Fe1 70.38(12) . . ?
C5 C4 H4 126.0 . . ?
C3 C4 H4 126.0 . . ?
Fe1 C4 H4 125.7 . . ?
C4 C5 C1 107.7(2) . . ?
C4 C5 Fe1 69.79(13) . . ?
C1 C5 Fe1 70.08(13) . . ?
C4 C5 H5 126.2 . . ?
C1 C5 H5 126.2 . . ?
Fe1 C5 H5 125.5 . . ?
C7 C6 C10 109.50(19) . . ?
C7 C6 Fe1 69.47(12) . . ?
C10 C6 Fe1 69.58(11) . . ?
C7 C6 H6 125.2 . . ?
C10 C6 H6 125.2 . . ?
Fe1 C6 H6 127.3 . . ?
C8 C7 C6 108.56(18) . . ?
C8 C7 Fe1 68.97(12) . . ?
C6 C7 Fe1 70.04(12) . . ?
C8 C7 H7 125.7 . . ?
C6 C7 H7 125.7 . . ?
Fe1 C7 H7 126.8 . . ?
C7 C8 C9 106.77(18) . . ?
C7 C8 Fe1 70.47(12) . . ?
C9 C8 Fe1 67.94(11) . . ?
C7 C8 H8 126.6 . . ?
C9 C8 H8 126.6 . . ?
Fe1 C8 H8 126.5 . . ?
C8 C9 C10 109.50(18) . . ?
C8 C9 S2 124.00(16) . . ?
C10 C9 S2 126.44(15) . . ?
C8 C9 Fe1 70.33(12) . . ?
C10 C9 Fe1 71.26(11) . . ?
S2 C9 Fe1 122.60(11) . . ?
C6 C10 C9 105.66(17) . . ?
C6 C10 C11 126.38(18) . . ?
C9 C10 C11 127.50(18) . . ?
C6 C10 Fe1 69.90(11) . . ?
C9 C10 Fe1 67.16(11) . . ?
C11 C10 Fe1 133.23(14) . . ?
C12 C11 C13 111.59(19) . . ?
C12 C11 C10 121.70(19) . . ?
C13 C11 C10 126.70(18) . . ?
C11 C12 S1 111.99(17) . . ?
C11 C12 H12 124.0 . . ?
S1 C12 H12 124.0 . . ?
C14 C13 C11 112.53(19) . . ?
C14 C13 H13 123.7 . . ?
C11 C13 H13 123.7 . . ?
C13 C14 S1 111.42(17) . . ?
C13 C14 H14 124.3 . . ?
S1 C14 H14 124.3 . . ?
C9 Fe1 C5 122.43(10) . . ?
C9 Fe1 C8 41.73(8) . . ?
C5 Fe1 C8 103.87(9) . . ?
C9 Fe1 C4 156.36(9) . . ?
C5 Fe1 C4 40.72(11) . . ?
C8 Fe1 C4 117.78(9) . . ?
C9 Fe1 C1 110.13(9) . . ?
C5 Fe1 C1 40.97(11) . . ?
C8 Fe1 C1 122.96(10) . . ?
C4 Fe1 C1 68.41(10) . . ?
C9 Fe1 C3 162.59(9) . . ?
C5 Fe1 C3 68.18(10) . . ?
C8 Fe1 C3 154.49(9) . . ?
C4 Fe1 C3 40.52(9) . . ?
C1 Fe1 C3 67.75(10) . . ?
C9 Fe1 C7 68.79(9) . . ?
C5 Fe1 C7 118.66(10) . . ?
C8 Fe1 C7 40.56(9) . . ?
C4 Fe1 C7 102.94(9) . . ?
C1 Fe1 C7 156.83(11) . . ?
C3 Fe1 C7 120.36(10) . . ?
C9 Fe1 C10 41.58(8) . . ?
C5 Fe1 C10 161.20(10) . . ?
C8 Fe1 C10 70.16(8) . . ?
C4 Fe1 C10 157.92(10) . . ?
C1 Fe1 C10 126.60(10) . . ?
C3 Fe1 C10 124.69(9) . . ?
C7 Fe1 C10 68.99(8) . . ?
C9 Fe1 C6 68.43(8) . . ?
C5 Fe1 C6 155.25(11) . . ?
C8 Fe1 C6 68.56(9) . . ?
C4 Fe1 C6 120.37(10) . . ?
C1 Fe1 C6 162.31(11) . . ?
C3 Fe1 C6 108.01(9) . . ?
C7 Fe1 C6 40.50(9) . . ?
C10 Fe1 C6 40.53(8) . . ?
C9 Fe1 C2 127.17(9) . . ?
C5 Fe1 C2 68.05(10) . . ?
C8 Fe1 C2 161.18(10) . . ?
C4 Fe1 C2 67.92(9) . . ?
C1 Fe1 C2 40.03(10) . . ?
C3 Fe1 C2 40.13(9) . . ?
C7 Fe1 C2 158.26(10) . . ?
C10 Fe1 C2 111.74(8) . . ?
C6 Fe1 C2 125.81(10) . . ?
C14 S1 C12 92.47(11) . . ?
O15 S2 O16 120.15(11) . . ?
O15 S2 F17 105.68(11) . . ?
O16 S2 F17 105.03(11) . . ?
O15 S2 C9 110.40(11) . . ?
O16 S2 C9 112.75(10) . . ?
F17 S2 C9 100.47(9) . . ?

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
C5 C1 C2 C3 -0.3(2) . . . . ?
Fe1 C1 C2 C3 58.76(15) . . . . ?
C5 C1 C2 Fe1 -59.08(15) . . . . ?
C1 C2 C3 C4 0.3(2) . . . . ?
Fe1 C2 C3 C4 58.97(15) . . . . ?
C1 C2 C3 Fe1 -58.65(15) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
Fe1 C3 C4 C5 59.57(15) . . . . ?
C2 C3 C4 Fe1 -59.75(15) . . . . ?
C3 C4 C5 C1 0.0(2) . . . . ?
Fe1 C4 C5 C1 60.11(15) . . . . ?
C3 C4 C5 Fe1 -60.13(15) . . . . ?
C2 C1 C5 C4 0.2(2) . . . . ?
Fe1 C1 C5 C4 -59.93(15) . . . . ?
C2 C1 C5 Fe1 60.14(15) . . . . ?
C10 C6 C7 C8 -0.2(2) . . . . ?
Fe1 C6 C7 C8 -58.35(14) . . . . ?
C10 C6 C7 Fe1 58.13(14) . . . . ?
C6 C7 C8 C9 0.5(2) . . . . ?
Fe1 C7 C8 C9 -58.46(13) . . . . ?
C6 C7 C8 Fe1 59.01(15) . . . . ?
C7 C8 C9 C10 -0.7(2) . . . . ?
Fe1 C8 C9 C10 -60.76(14) . . . . ?
C7 C8 C9 S2 176.75(15) . . . . ?
Fe1 C8 C9 S2 116.68(15) . . . . ?
C7 C8 C9 Fe1 60.08(14) . . . . ?
C7 C6 C10 C9 -0.2(2) . . . . ?
Fe1 C6 C10 C9 57.87(13) . . . . ?
C7 C6 C10 C11 172.42(19) . . . . ?
Fe1 C6 C10 C11 -129.5(2) . . . . ?
C7 C6 C10 Fe1 -58.07(15) . . . . ?
C8 C9 C10 C6 0.5(2) . . . . ?
S2 C9 C10 C6 -176.81(15) . . . . ?
Fe1 C9 C10 C6 -59.64(13) . . . . ?
C8 C9 C10 C11 -171.96(19) . . . . ?
S2 C9 C10 C11 10.7(3) . . . . ?
Fe1 C9 C10 C11 127.9(2) . . . . ?
C8 C9 C10 Fe1 60.18(14) . . . . ?
S2 C9 C10 Fe1 -117.17(16) . . . . ?
C6 C10 C11 C12 -71.7(3) . . . . ?
C9 C10 C11 C12 99.3(3) . . . . ?
Fe1 C10 C11 C12 -167.87(17) . . . . ?
C6 C10 C11 C13 108.0(3) . . . . ?
C9 C10 C11 C13 -81.0(3) . . . . ?
Fe1 C10 C11 C13 11.8(3) . . . . ?
C13 C11 C12 S1 -0.1(2) . . . . ?
C10 C11 C12 S1 179.65(15) . . . . ?
C12 C11 C13 C14 0.3(3) . . . . ?
C10 C11 C13 C14 -179.4(2) . . . . ?
C11 C13 C14 S1 -0.4(3) . . . . ?
C13 C14 S1 C12 0.32(19) . . . . ?
C11 C12 S1 C14 -0.13(18) . . . . ?
C8 C9 S2 O15 -7.3(2) . . . . ?
C10 C9 S2 O15 169.71(18) . . . . ?
Fe1 C9 S2 O15 79.81(15) . . . . ?
C8 C9 S2 O16 -144.75(17) . . . . ?
C10 C9 S2 O16 32.2(2) . . . . ?
Fe1 C9 S2 O16 -57.66(15) . . . . ?
C8 C9 S2 F17 103.93(18) . . . . ?
C10 C9 S2 F17 -79.07(19) . . . . ?
Fe1 C9 S2 F17 -168.97(12) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


####################################################################### 
# 
# 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_WE17991
_database_code_depnum_ccdc_archive 'CCDC 2189769'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;ISCR
France
;
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2022-09-25 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 11 janvier 2022                                          #
#------------------------------------------------------------------------------#


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H14 Fe N2 O4 S'
_chemical_formula_sum            'C15 H14 Fe N2 O4 S'
_chemical_formula_weight         374.19
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   19.288(2)
_cell_length_b                   5.8549(7)
_cell_length_c                   13.2527(17)
_cell_angle_alpha                90
_cell_angle_beta                 99.843(5)
_cell_angle_gamma                90
_cell_volume                     1474.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9064
_cell_measurement_theta_min      3.1202
_cell_measurement_theta_max      27.4723
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      -0.0677905
_diffrn_orient_matrix_UB_21      0.0124399
_diffrn_orient_matrix_UB_31      -0.0333880
_diffrn_orient_matrix_UB_12      -0.0704484
_diffrn_orient_matrix_UB_22      0.0272406
_diffrn_orient_matrix_UB_32      0.1531869
_diffrn_orient_matrix_UB_13      0.0031958
_diffrn_orient_matrix_UB_23      0.0519469
_diffrn_orient_matrix_UB_33      -0.0077678


#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.090
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             768
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.186
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.791
_exptl_absorpt_correction_T_max  0.899

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

# Software                   : BIS V6.2.15/2021-03-15 && APEX4 2021.10-0       #
# Number of scans            :        3                                        #
# Total number of frames [*] :      194                                        #
# Total length of scans  [*] :   194.00 (deg.)                                 #
# Rotation speed         [*] :     6.00 sec./deg.                              #
# Total exposition time  [*] :         19.4 min.                               #
#                                                                              #
#  [*] fast scan not included                                                  #
#                                                                              #
#    Scan  Time(s) Width DX(mm) Frames Range 2Theta  Omega    Phi    Chi  T(K) #
#..............................................................................#
#                                                                              #
#  1 Fast     1.0  1.00    34.0   180  180.0    0.0    0.0    0.0   54.7 150.0 #
#  2 Omega    6.0  1.00    34.0    97   97.0    0.1    2.5  216.0  -44.5 150.0 #
#  3 Omega    6.0  1.00    34.0    97   97.0    0.1    2.5   72.0  -44.5 150.0 #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.00
_diffrn_source_voltage           50.00
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0298
_diffrn_reflns_av_r_equivalents  0.0276
_diffrn_reflns_number            10694
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.120
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_reflns_number_total             3349
_reflns_number_gt                3110
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2021)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0200P)²+1.2398P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         3349
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0275
_refine_ls_wR_factor_ref         0.0660
_refine_ls_wR_factor_gt          0.0645
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.057

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.70757(2) 0.51805(4) 0.48022(2) 0.01357(8) Uani 1 1 d . . . . .
C1 C 0.69518(11) 0.2461(4) 0.38236(14) 0.0299(4) Uani 1 1 d . . . . .
H1 H 0.695670 0.089777 0.401619 0.036 Uiso 1 1 calc R U . . .
C2 C 0.75450(10) 0.3774(4) 0.36747(14) 0.0295(4) Uani 1 1 d . . . . .
H2 H 0.801656 0.324363 0.375069 0.035 Uiso 1 1 calc R U . . .
C3 C 0.73111(10) 0.6006(4) 0.33940(14) 0.0262(4) Uani 1 1 d . . . . .
H3 H 0.759782 0.724199 0.324885 0.031 Uiso 1 1 calc R U . . .
C4 C 0.65754(9) 0.6081(4) 0.33665(13) 0.0241(4) Uani 1 1 d . . . . .
H4 H 0.628215 0.737725 0.319736 0.029 Uiso 1 1 calc R U . . .
C5 C 0.63504(10) 0.3896(4) 0.36342(14) 0.0266(4) Uani 1 1 d . . . . .
H5 H 0.588156 0.346653 0.367900 0.032 Uiso 1 1 calc R U . . .
C6 C 0.72287(8) 0.3878(3) 0.62477(12) 0.0150(3) Uani 1 1 d . . . . .
H6 H 0.724698 0.230581 0.642831 0.018 Uiso 1 1 calc R U . . .
C7 C 0.78029(8) 0.5288(3) 0.60844(12) 0.0153(3) Uani 1 1 d . . . . .
C8 C 0.75583(8) 0.7560(3) 0.58230(13) 0.0173(3) Uani 1 1 d . . . . .
H8 H 0.783445 0.881996 0.567457 0.021 Uiso 1 1 calc R U . . .
C9 C 0.68238(8) 0.7559(3) 0.58294(13) 0.0168(3) Uani 1 1 d . . . . .
H9 H 0.651849 0.883559 0.568822 0.020 Uiso 1 1 calc R U . . .
C10 C 0.66208(8) 0.5312(3) 0.60842(12) 0.0151(3) Uani 1 1 d . . . . .
C11 C 0.58934(8) 0.4624(3) 0.61466(12) 0.0164(3) Uani 1 1 d . . . . .
O12 O 0.54210(6) 0.5957(2) 0.61927(11) 0.0252(3) Uani 1 1 d . . . . .
O13 O 0.58190(6) 0.2361(2) 0.61588(10) 0.0200(3) Uani 1 1 d . . . . .
C14 C 0.51261(9) 0.1563(3) 0.62715(15) 0.0229(4) Uani 1 1 d . . . . .
H14A H 0.500968 0.213516 0.691717 0.034 Uiso 1 1 calc R U . . .
H14B H 0.512102 -0.011043 0.627519 0.034 Uiso 1 1 calc R U . . .
H14C H 0.477844 0.212502 0.569852 0.034 Uiso 1 1 calc R U . . .
S1 S 0.86637(2) 0.43695(7) 0.61471(3) 0.01554(10) Uani 1 1 d . . . . .
O15 O 0.86743(6) 0.1937(2) 0.61408(10) 0.0230(3) Uani 1 1 d . . . . .
O16 O 0.89961(6) 0.5676(2) 0.54610(10) 0.0233(3) Uani 1 1 d . . . . .
N17 N 0.90587(7) 0.5229(3) 0.73084(11) 0.0170(3) Uani 1 1 d . . . . .
C18 C 0.93583(9) 0.7342(3) 0.75374(15) 0.0230(4) Uani 1 1 d . . . . .
H18 H 0.946486 0.845687 0.706623 0.028 Uiso 1 1 calc R U . . .
C19 C 0.94703(10) 0.7504(4) 0.85744(15) 0.0305(4) Uani 1 1 d . . . . .
H19 H 0.968043 0.873696 0.898211 0.037 Uiso 1 1 calc R U . . .
C20 C 0.92087(10) 0.5459(4) 0.89144(15) 0.0308(4) Uani 1 1 d . . . . .
H20 H 0.921664 0.511080 0.961642 0.037 Uiso 1 1 calc R U . . .
N21 N 0.89509(8) 0.4070(3) 0.81608(12) 0.0249(3) Uani 1 1 d . . . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_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 2.0109(16) . ?
Fe1 C6 2.0361(16) . ?
Fe1 C1 2.0415(19) . ?
Fe1 C10 2.0426(16) . ?
Fe1 C5 2.0443(17) . ?
Fe1 C2 2.0475(18) . ?
Fe1 C4 2.0498(18) . ?
Fe1 C8 2.0510(17) . ?
Fe1 C3 2.0525(18) . ?
Fe1 C9 2.0628(17) . ?
C1 C5 1.419(3) . ?
C1 C2 1.420(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.412(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.414(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.416(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.427(2) . ?
C6 C10 1.428(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.434(2) . ?
C7 S1 1.7334(16) . ?
C8 C9 1.418(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.429(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.476(2) . ?
C11 O12 1.209(2) . ?
C11 O13 1.333(2) . ?
O13 C14 1.4473(19) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
S1 O16 1.4223(13) . ?
S1 O15 1.4243(13) . ?
S1 N17 1.6738(15) . ?
N17 N21 1.364(2) . ?
N17 C18 1.377(2) . ?
C18 C19 1.357(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.403(3) . ?
C19 H19 0.9500 . ?
C20 N21 1.317(3) . ?
C20 H20 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
C7 Fe1 C6 41.30(6) . . ?
C7 Fe1 C1 123.38(7) . . ?
C6 Fe1 C1 106.74(8) . . ?
C7 Fe1 C10 68.45(6) . . ?
C6 Fe1 C10 41.00(6) . . ?
C1 Fe1 C10 122.52(8) . . ?
C7 Fe1 C5 159.97(8) . . ?
C6 Fe1 C5 123.01(7) . . ?
C1 Fe1 C5 40.65(8) . . ?
C10 Fe1 C5 107.94(7) . . ?
C7 Fe1 C2 107.32(7) . . ?
C6 Fe1 C2 121.67(8) . . ?
C1 Fe1 C2 40.64(9) . . ?
C10 Fe1 C2 158.22(8) . . ?
C5 Fe1 C2 68.29(8) . . ?
C7 Fe1 C4 157.82(8) . . ?
C6 Fe1 C4 159.92(7) . . ?
C1 Fe1 C4 68.01(8) . . ?
C10 Fe1 C4 124.15(7) . . ?
C5 Fe1 C4 40.47(8) . . ?
C2 Fe1 C4 67.84(8) . . ?
C7 Fe1 C8 41.33(7) . . ?
C6 Fe1 C8 69.97(7) . . ?
C1 Fe1 C8 159.94(8) . . ?
C10 Fe1 C8 68.70(7) . . ?
C5 Fe1 C8 157.53(8) . . ?
C2 Fe1 C8 123.17(8) . . ?
C4 Fe1 C8 121.73(8) . . ?
C7 Fe1 C3 122.02(7) . . ?
C6 Fe1 C3 157.64(7) . . ?
C1 Fe1 C3 68.05(8) . . ?
C10 Fe1 C3 160.16(8) . . ?
C5 Fe1 C3 68.12(8) . . ?
C2 Fe1 C3 40.28(9) . . ?
C4 Fe1 C3 40.32(7) . . ?
C8 Fe1 C3 107.08(8) . . ?
C7 Fe1 C9 68.30(7) . . ?
C6 Fe1 C9 69.19(7) . . ?
C1 Fe1 C9 158.52(8) . . ?
C10 Fe1 C9 40.75(7) . . ?
C5 Fe1 C9 122.70(7) . . ?
C2 Fe1 C9 159.47(8) . . ?
C4 Fe1 C9 108.19(7) . . ?
C8 Fe1 C9 40.33(6) . . ?
C3 Fe1 C9 123.69(8) . . ?
C5 C1 C2 107.99(18) . . ?
C5 C1 Fe1 69.78(11) . . ?
C2 C1 Fe1 69.91(11) . . ?
C5 C1 H1 126.0 . . ?
C2 C1 H1 126.0 . . ?
Fe1 C1 H1 125.9 . . ?
C3 C2 C1 108.00(16) . . ?
C3 C2 Fe1 70.05(10) . . ?
C1 C2 Fe1 69.45(11) . . ?
C3 C2 H2 126.0 . . ?
C1 C2 H2 126.0 . . ?
Fe1 C2 H2 126.1 . . ?
C2 C3 C4 108.04(18) . . ?
C2 C3 Fe1 69.67(11) . . ?
C4 C3 Fe1 69.74(10) . . ?
C2 C3 H3 126.0 . . ?
C4 C3 H3 126.0 . . ?
Fe1 C3 H3 126.2 . . ?
C3 C4 C5 108.35(17) . . ?
C3 C4 Fe1 69.94(10) . . ?
C5 C4 Fe1 69.55(10) . . ?
C3 C4 H4 125.8 . . ?
C5 C4 H4 125.8 . . ?
Fe1 C4 H4 126.3 . . ?
C4 C5 C1 107.62(17) . . ?
C4 C5 Fe1 69.98(10) . . ?
C1 C5 Fe1 69.57(10) . . ?
C4 C5 H5 126.2 . . ?
C1 C5 H5 126.2 . . ?
Fe1 C5 H5 125.8 . . ?
C7 C6 C10 105.95(14) . . ?
C7 C6 Fe1 68.40(9) . . ?
C10 C6 Fe1 69.74(9) . . ?
C7 C6 H6 127.0 . . ?
C10 C6 H6 127.0 . . ?
Fe1 C6 H6 126.4 . . ?
C6 C7 C8 109.96(14) . . ?
C6 C7 S1 125.10(13) . . ?
C8 C7 S1 124.90(12) . . ?
C6 C7 Fe1 70.30(9) . . ?
C8 C7 Fe1 70.84(9) . . ?
S1 C7 Fe1 123.70(9) . . ?
C9 C8 C7 106.63(14) . . ?
C9 C8 Fe1 70.28(9) . . ?
C7 C8 Fe1 67.83(9) . . ?
C9 C8 H8 126.7 . . ?
C7 C8 H8 126.7 . . ?
Fe1 C8 H8 126.7 . . ?
C8 C9 C10 108.41(14) . . ?
C8 C9 Fe1 69.39(9) . . ?
C10 C9 Fe1 68.87(9) . . ?
C8 C9 H9 125.8 . . ?
C10 C9 H9 125.8 . . ?
Fe1 C9 H9 127.5 . . ?
C6 C10 C9 109.04(14) . . ?
C6 C10 C11 126.48(15) . . ?
C9 C10 C11 124.47(14) . . ?
C6 C10 Fe1 69.26(9) . . ?
C9 C10 Fe1 70.39(9) . . ?
C11 C10 Fe1 125.74(11) . . ?
O12 C11 O13 123.87(15) . . ?
O12 C11 C10 123.95(16) . . ?
O13 C11 C10 112.17(14) . . ?
C11 O13 C14 115.16(13) . . ?
O13 C14 H14A 109.5 . . ?
O13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O16 S1 O15 121.71(8) . . ?
O16 S1 N17 104.00(7) . . ?
O15 S1 N17 107.53(8) . . ?
O16 S1 C7 109.59(8) . . ?
O15 S1 C7 108.94(8) . . ?
N17 S1 C7 103.45(8) . . ?
N21 N17 C18 112.45(15) . . ?
N21 N17 S1 120.15(12) . . ?
C18 N17 S1 125.50(13) . . ?
C19 C18 N17 105.92(17) . . ?
C19 C18 H18 127.0 . . ?
N17 C18 H18 127.0 . . ?
C18 C19 C20 105.16(17) . . ?
C18 C19 H19 127.4 . . ?
C20 C19 H19 127.4 . . ?
N21 C20 C19 113.13(18) . . ?
N21 C20 H20 123.4 . . ?
C19 C20 H20 123.4 . . ?
C20 N21 N17 103.29(16) . . ?

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
C5 C1 C2 C3 -0.1(2) . . . . ?
Fe1 C1 C2 C3 -59.68(13) . . . . ?
C5 C1 C2 Fe1 59.62(13) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
Fe1 C2 C3 C4 -59.40(13) . . . . ?
C1 C2 C3 Fe1 59.30(13) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
Fe1 C3 C4 C5 -59.14(13) . . . . ?
C2 C3 C4 Fe1 59.36(13) . . . . ?
C3 C4 C5 C1 -0.2(2) . . . . ?
Fe1 C4 C5 C1 -59.63(12) . . . . ?
C3 C4 C5 Fe1 59.38(13) . . . . ?
C2 C1 C5 C4 0.2(2) . . . . ?
Fe1 C1 C5 C4 59.89(13) . . . . ?
C2 C1 C5 Fe1 -59.70(13) . . . . ?
C10 C6 C7 C8 -0.04(18) . . . . ?
Fe1 C6 C7 C8 59.93(12) . . . . ?
C10 C6 C7 S1 -177.91(12) . . . . ?
Fe1 C6 C7 S1 -117.94(13) . . . . ?
C10 C6 C7 Fe1 -59.97(11) . . . . ?
C6 C7 C8 C9 0.27(19) . . . . ?
S1 C7 C8 C9 178.15(12) . . . . ?
Fe1 C7 C8 C9 59.88(11) . . . . ?
C6 C7 C8 Fe1 -59.60(11) . . . . ?
S1 C7 C8 Fe1 118.27(13) . . . . ?
C7 C8 C9 C10 -0.39(19) . . . . ?
Fe1 C8 C9 C10 57.91(12) . . . . ?
C7 C8 C9 Fe1 -58.31(11) . . . . ?
C7 C6 C10 C9 -0.20(18) . . . . ?
Fe1 C6 C10 C9 -59.30(11) . . . . ?
C7 C6 C10 C11 178.88(15) . . . . ?
Fe1 C6 C10 C11 119.78(17) . . . . ?
C7 C6 C10 Fe1 59.10(11) . . . . ?
C8 C9 C10 C6 0.38(19) . . . . ?
Fe1 C9 C10 C6 58.61(11) . . . . ?
C8 C9 C10 C11 -178.73(15) . . . . ?
Fe1 C9 C10 C11 -120.49(16) . . . . ?
C8 C9 C10 Fe1 -58.23(12) . . . . ?
C6 C10 C11 O12 165.57(17) . . . . ?
C9 C10 C11 O12 -15.5(3) . . . . ?
Fe1 C10 C11 O12 -105.04(19) . . . . ?
C6 C10 C11 O13 -13.7(2) . . . . ?
C9 C10 C11 O13 165.27(15) . . . . ?
Fe1 C10 C11 O13 75.71(18) . . . . ?
O12 C11 O13 C14 -2.2(2) . . . . ?
C10 C11 O13 C14 177.01(14) . . . . ?
C6 C7 S1 O16 149.15(14) . . . . ?
C8 C7 S1 O16 -28.41(17) . . . . ?
Fe1 C7 S1 O16 60.68(12) . . . . ?
C6 C7 S1 O15 13.76(17) . . . . ?
C8 C7 S1 O15 -163.80(14) . . . . ?
Fe1 C7 S1 O15 -74.71(12) . . . . ?
C6 C7 S1 N17 -100.41(15) . . . . ?
C8 C7 S1 N17 82.03(15) . . . . ?
Fe1 C7 S1 N17 171.12(10) . . . . ?
O16 S1 N17 N21 -169.47(13) . . . . ?
O15 S1 N17 N21 -39.16(15) . . . . ?
C7 S1 N17 N21 76.02(14) . . . . ?
O16 S1 N17 C18 27.45(16) . . . . ?
O15 S1 N17 C18 157.76(14) . . . . ?
C7 S1 N17 C18 -87.06(15) . . . . ?
N21 N17 C18 C19 2.3(2) . . . . ?
S1 N17 C18 C19 166.51(13) . . . . ?
N17 C18 C19 C20 -1.5(2) . . . . ?
C18 C19 C20 N21 0.3(2) . . . . ?
C19 C20 N21 N17 1.0(2) . . . . ?
C18 N17 N21 C20 -2.0(2) . . . . ?
S1 N17 N21 C20 -167.18(13) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


####################################################################### 
# 
# 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_WE13071
_database_code_depnum_ccdc_archive 'CCDC 2189766'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;ISCR
France
;
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2022-09-25 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 05 fevrier 2021                                          #
#------------------------------------------------------------------------------#


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H17 F Fe O4 S'
_chemical_formula_sum            'C18 H17 F Fe O4 S'
_chemical_formula_weight         404.22
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#


_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.9976(8)
_cell_length_b                   7.6106(7)
_cell_length_c                   27.200(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.676(4)
_cell_angle_gamma                90
_cell_volume                     1650.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9344
_cell_measurement_theta_min      2.6040
_cell_measurement_theta_max      27.5011
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      -0.0741226
_diffrn_orient_matrix_UB_21      0.0504436
_diffrn_orient_matrix_UB_31      0.0877514
_diffrn_orient_matrix_UB_12      -0.0145126
_diffrn_orient_matrix_UB_22      -0.1181389
_diffrn_orient_matrix_UB_32      0.0556531
_diffrn_orient_matrix_UB_13      0.0276061
_diffrn_orient_matrix_UB_23      0.0075693
_diffrn_orient_matrix_UB_33      0.0232668


#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.240
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             832
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.641
_exptl_absorpt_correction_T_max  0.773

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

# Software                   : BIS V6.2.1/2016-03-01                           #
# Number of scans            :        2                                        #
# Total number of frames [*] :      430                                        #
# Total length of scans  [*] :   215.00 (deg.)                                 #
# Rotation speed         [*] :    10.00 sec./deg.                              #
# Total exposition time  [*] :         35.8 min.                               #
#                                                                              #
#  [*] fast scan not included                                                  #
#                                                                              #
# Measurement mode           : shutterless mode                                #
#                                                                              #
#    Scan  Time(s)  Width  DX (mm)  Frames  Theta  Omega    Phi    Chi   T(K)  #
#..............................................................................#
#                                                                              #
#  1 Phi       5.0   0.50     34.0     430   0.27 270.94 248.52  23.00 150.00  #
#  2 Fast      1.0   1.00     34.0     180   0.00 360.00   0.00  54.74 150.00  #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.00
_diffrn_source_voltage           50.00
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0306
_diffrn_reflns_av_r_equivalents  0.0301
_diffrn_reflns_number            13741
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.555
_diffrn_reflns_theta_max         27.511
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_reflns_number_total             3776
_reflns_number_gt                3506
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2020)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0327P)²+1.6078P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         3776
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0746
_refine_ls_wR_factor_gt          0.0726
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.003
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.084

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'
F F 0.0171 0.0103 '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'
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'

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 0.78039(3) 0.16406(3) 0.42222(2) 0.01139(8) Uani 1 1 d . . . . .
C1 C 0.7775(2) 0.0133(2) 0.35976(7) 0.0208(4) Uani 1 1 d . . . . .
H1 H 0.731818 0.046875 0.327795 0.025 Uiso 1 1 calc R U . . .
C2 C 0.6901(2) -0.0732(2) 0.39605(7) 0.0232(4) Uani 1 1 d . . . . .
H2 H 0.575659 -0.107931 0.392555 0.028 Uiso 1 1 calc R U . . .
C3 C 0.8030(2) -0.0992(2) 0.43858(7) 0.0223(4) Uani 1 1 d . . . . .
H3 H 0.777450 -0.154311 0.468403 0.027 Uiso 1 1 calc R U . . .
C4 C 0.9617(2) -0.0278(2) 0.42844(7) 0.0199(3) Uani 1 1 d . . . . .
H4 H 1.060416 -0.026527 0.450363 0.024 Uiso 1 1 calc R U . . .
C5 C 0.9455(2) 0.0412(2) 0.37956(7) 0.0186(3) Uani 1 1 d . . . . .
H5 H 1.031857 0.096142 0.363103 0.022 Uiso 1 1 calc R U . . .
C6 C 0.6760(2) 0.2773(2) 0.48034(6) 0.0161(3) Uani 1 1 d . . . . .
H6 H 0.635190 0.217396 0.507573 0.019 Uiso 1 1 calc R U . . .
C7 C 0.8405(2) 0.3448(2) 0.47730(6) 0.0178(3) Uani 1 1 d . . . . .
H7 H 0.929604 0.338055 0.502544 0.021 Uiso 1 1 calc R U . . .
C8 C 0.8497(2) 0.4241(2) 0.43019(6) 0.0158(3) Uani 1 1 d . . . . .
H8 H 0.946585 0.478445 0.418983 0.019 Uiso 1 1 calc R U . . .
C9 C 0.6905(2) 0.4092(2) 0.40230(6) 0.0132(3) Uani 1 1 d . . . . .
C10 C 0.5833(2) 0.3174(2) 0.43415(6) 0.0137(3) Uani 1 1 d . . . . .
S1 S 0.38527(5) 0.23552(5) 0.41958(2) 0.01622(10) Uani 1 1 d . . . . .
O11 O 0.35704(16) 0.08553(18) 0.44901(5) 0.0254(3) Uani 1 1 d . . . . .
O12 O 0.34101(16) 0.23319(18) 0.36807(5) 0.0238(3) Uani 1 1 d . . . . .
F13 F 0.27236(14) 0.38113(15) 0.44108(4) 0.0270(2) Uani 1 1 d . . . . .
C14 C 0.6547(2) 0.4797(2) 0.35188(6) 0.0141(3) Uani 1 1 d . . . . .
C15 C 0.7690(2) 0.4486(2) 0.31676(6) 0.0160(3) Uani 1 1 d . . . . .
H15 H 0.865579 0.378853 0.325281 0.019 Uiso 1 1 calc R U . . .
C16 C 0.7436(2) 0.5180(2) 0.26956(6) 0.0186(3) Uani 1 1 d . . . . .
C17 C 0.6040(2) 0.6226(2) 0.25721(7) 0.0222(4) Uani 1 1 d . . . . .
H17 H 0.586373 0.671166 0.225027 0.027 Uiso 1 1 calc R U . . .
C18 C 0.4905(2) 0.6559(2) 0.29199(7) 0.0208(4) Uani 1 1 d . . . . .
H18 H 0.395278 0.727495 0.283448 0.025 Uiso 1 1 calc R U . . .
C19 C 0.5147(2) 0.5854(2) 0.33938(6) 0.0160(3) Uani 1 1 d . . . . .
O20 O 0.84946(17) 0.48764(17) 0.23284(5) 0.0238(3) Uani 1 1 d . . . . .
C21 C 0.9843(3) 0.3682(3) 0.24424(7) 0.0268(4) Uani 1 1 d . . . . .
H21A H 1.062298 0.418428 0.270158 0.040 Uiso 1 1 calc R U . . .
H21B H 1.043535 0.347127 0.214631 0.040 Uiso 1 1 calc R U . . .
H21C H 0.939917 0.256852 0.255755 0.040 Uiso 1 1 calc R U . . .
O22 O 0.41336(15) 0.61796(16) 0.37656(5) 0.0192(3) Uani 1 1 d . . . . .
C23 C 0.2574(2) 0.7034(3) 0.36407(8) 0.0284(4) Uani 1 1 d . . . . .
H23A H 0.277987 0.820533 0.350862 0.043 Uiso 1 1 calc R U . . .
H23B H 0.195764 0.714431 0.393610 0.043 Uiso 1 1 calc R U . . .
H23C H 0.191153 0.634097 0.339142 0.043 Uiso 1 1 calc R U . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_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 C10 2.0083(16) . ?
Fe1 C6 2.0382(16) . ?
Fe1 C2 2.0507(17) . ?
Fe1 C1 2.0485(17) . ?
Fe1 C5 2.0529(17) . ?
Fe1 C9 2.0563(16) . ?
Fe1 C4 2.0551(17) . ?
Fe1 C3 2.0576(17) . ?
Fe1 C7 2.0614(17) . ?
Fe1 C8 2.0618(16) . ?
C1 C2 1.417(3) . ?
C1 C5 1.422(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.422(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.428(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.425(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.421(2) . ?
C6 C10 1.438(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.424(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.433(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.447(2) . ?
C9 C14 1.479(2) . ?
C10 S1 1.7182(17) . ?
S1 O12 1.4170(14) . ?
S1 O11 1.4229(13) . ?
S1 F13 1.5722(11) . ?
C14 C15 1.395(2) . ?
C14 C19 1.398(2) . ?
C15 C16 1.388(2) . ?
C15 H15 0.9500 . ?
C16 O20 1.380(2) . ?
C16 C17 1.390(3) . ?
C17 C18 1.386(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.395(2) . ?
C18 H18 0.9500 . ?
C19 O22 1.369(2) . ?
O20 C21 1.425(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
O22 C23 1.423(2) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
C10 Fe1 C6 41.63(6) . . ?
C10 Fe1 C2 108.00(7) . . ?
C6 Fe1 C2 119.13(7) . . ?
C10 Fe1 C1 120.23(7) . . ?
C6 Fe1 C1 154.48(7) . . ?
C2 Fe1 C1 40.46(8) . . ?
C10 Fe1 C5 154.88(7) . . ?
C6 Fe1 C5 162.55(7) . . ?
C2 Fe1 C5 68.11(7) . . ?
C1 Fe1 C5 40.58(7) . . ?
C10 Fe1 C9 41.69(6) . . ?
C6 Fe1 C9 70.38(6) . . ?
C2 Fe1 C9 127.01(7) . . ?
C1 Fe1 C9 108.03(7) . . ?
C5 Fe1 C9 119.45(7) . . ?
C10 Fe1 C4 163.16(7) . . ?
C6 Fe1 C4 124.57(7) . . ?
C2 Fe1 C4 68.21(7) . . ?
C1 Fe1 C4 68.32(7) . . ?
C5 Fe1 C4 40.61(7) . . ?
C9 Fe1 C4 153.60(7) . . ?
C10 Fe1 C3 125.96(7) . . ?
C6 Fe1 C3 106.16(7) . . ?
C2 Fe1 C3 40.51(8) . . ?
C1 Fe1 C3 68.21(8) . . ?
C5 Fe1 C3 68.24(7) . . ?
C9 Fe1 C3 164.46(7) . . ?
C4 Fe1 C3 40.63(7) . . ?
C10 Fe1 C7 68.56(7) . . ?
C6 Fe1 C7 40.55(7) . . ?
C2 Fe1 C7 153.43(8) . . ?
C1 Fe1 C7 164.27(8) . . ?
C5 Fe1 C7 126.30(7) . . ?
C9 Fe1 C7 69.02(6) . . ?
C4 Fe1 C7 107.04(7) . . ?
C3 Fe1 C7 118.77(7) . . ?
C10 Fe1 C8 68.49(7) . . ?
C6 Fe1 C8 68.67(7) . . ?
C2 Fe1 C8 164.97(8) . . ?
C1 Fe1 C8 127.55(7) . . ?
C5 Fe1 C8 108.46(7) . . ?
C9 Fe1 C8 40.73(6) . . ?
C4 Fe1 C8 119.43(7) . . ?
C3 Fe1 C8 153.36(8) . . ?
C7 Fe1 C8 40.40(7) . . ?
C2 C1 C5 108.04(16) . . ?
C2 C1 Fe1 69.85(10) . . ?
C5 C1 Fe1 69.88(9) . . ?
C2 C1 H1 126.0 . . ?
C5 C1 H1 126.0 . . ?
Fe1 C1 H1 125.9 . . ?
C1 C2 C3 108.35(16) . . ?
C1 C2 Fe1 69.69(10) . . ?
C3 C2 Fe1 70.01(10) . . ?
C1 C2 H2 125.8 . . ?
C3 C2 H2 125.8 . . ?
Fe1 C2 H2 126.1 . . ?
C2 C3 C4 107.77(16) . . ?
C2 C3 Fe1 69.49(10) . . ?
C4 C3 Fe1 69.59(10) . . ?
C2 C3 H3 126.1 . . ?
C4 C3 H3 126.1 . . ?
Fe1 C3 H3 126.4 . . ?
C5 C4 C3 107.82(16) . . ?
C5 C4 Fe1 69.61(9) . . ?
C3 C4 Fe1 69.78(10) . . ?
C5 C4 H4 126.1 . . ?
C3 C4 H4 126.1 . . ?
Fe1 C4 H4 126.1 . . ?
C4 C5 C1 108.02(16) . . ?
C4 C5 Fe1 69.78(10) . . ?
C1 C5 Fe1 69.54(10) . . ?
C4 C5 H5 126.0 . . ?
C1 C5 H5 126.0 . . ?
Fe1 C5 H5 126.3 . . ?
C7 C6 C10 106.62(14) . . ?
C7 C6 Fe1 70.61(10) . . ?
C10 C6 Fe1 68.07(9) . . ?
C7 C6 H6 126.7 . . ?
C10 C6 H6 126.7 . . ?
Fe1 C6 H6 126.2 . . ?
C6 C7 C8 108.79(15) . . ?
C6 C7 Fe1 68.85(9) . . ?
C8 C7 Fe1 69.82(9) . . ?
C6 C7 H7 125.6 . . ?
C8 C7 H7 125.6 . . ?
Fe1 C7 H7 127.3 . . ?
C7 C8 C9 109.50(15) . . ?
C7 C8 Fe1 69.79(9) . . ?
C9 C8 Fe1 69.43(9) . . ?
C7 C8 H8 125.3 . . ?
C9 C8 H8 125.3 . . ?
Fe1 C8 H8 127.1 . . ?
C8 C9 C10 105.38(14) . . ?
C8 C9 C14 124.00(15) . . ?
C10 C9 C14 130.62(15) . . ?
C8 C9 Fe1 69.84(9) . . ?
C10 C9 Fe1 67.38(9) . . ?
C14 C9 Fe1 127.63(11) . . ?
C6 C10 C9 109.71(14) . . ?
C6 C10 S1 121.62(13) . . ?
C9 C10 S1 128.08(13) . . ?
C6 C10 Fe1 70.30(9) . . ?
C9 C10 Fe1 70.93(9) . . ?
S1 C10 Fe1 118.23(9) . . ?
O12 S1 O11 120.53(9) . . ?
O12 S1 F13 105.78(8) . . ?
O11 S1 F13 103.53(7) . . ?
O12 S1 C10 112.58(8) . . ?
O11 S1 C10 110.28(8) . . ?
F13 S1 C10 101.85(7) . . ?
C15 C14 C19 119.18(15) . . ?
C15 C14 C9 119.02(15) . . ?
C19 C14 C9 121.68(15) . . ?
C16 C15 C14 120.94(16) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
O20 C16 C15 123.62(16) . . ?
O20 C16 C17 116.67(15) . . ?
C15 C16 C17 119.70(16) . . ?
C18 C17 C16 119.82(16) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 120.73(16) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
O22 C19 C18 124.53(16) . . ?
O22 C19 C14 115.79(15) . . ?
C18 C19 C14 119.62(16) . . ?
C16 O20 C21 116.57(14) . . ?
O20 C21 H21A 109.5 . . ?
O20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 O22 C23 117.81(14) . . ?
O22 C23 H23A 109.5 . . ?
O22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
C5 C1 C2 C3 0.13(19) . . . . ?
Fe1 C1 C2 C3 -59.54(12) . . . . ?
C5 C1 C2 Fe1 59.68(12) . . . . ?
C1 C2 C3 C4 0.06(19) . . . . ?
Fe1 C2 C3 C4 -59.28(12) . . . . ?
C1 C2 C3 Fe1 59.34(12) . . . . ?
C2 C3 C4 C5 -0.23(19) . . . . ?
Fe1 C3 C4 C5 -59.45(12) . . . . ?
C2 C3 C4 Fe1 59.21(12) . . . . ?
C3 C4 C5 C1 0.32(19) . . . . ?
Fe1 C4 C5 C1 -59.23(12) . . . . ?
C3 C4 C5 Fe1 59.55(12) . . . . ?
C2 C1 C5 C4 -0.28(19) . . . . ?
Fe1 C1 C5 C4 59.38(12) . . . . ?
C2 C1 C5 Fe1 -59.66(12) . . . . ?
C10 C6 C7 C8 -0.28(18) . . . . ?
Fe1 C6 C7 C8 58.50(12) . . . . ?
C10 C6 C7 Fe1 -58.78(11) . . . . ?
C6 C7 C8 C9 0.25(19) . . . . ?
Fe1 C7 C8 C9 58.16(11) . . . . ?
C6 C7 C8 Fe1 -57.92(11) . . . . ?
C7 C8 C9 C10 -0.11(18) . . . . ?
Fe1 C8 C9 C10 58.27(10) . . . . ?
C7 C8 C9 C14 179.15(14) . . . . ?
Fe1 C8 C9 C14 -122.47(15) . . . . ?
C7 C8 C9 Fe1 -58.38(11) . . . . ?
C7 C6 C10 C9 0.21(18) . . . . ?
Fe1 C6 C10 C9 -60.20(11) . . . . ?
C7 C6 C10 S1 172.10(12) . . . . ?
Fe1 C6 C10 S1 111.68(12) . . . . ?
C7 C6 C10 Fe1 60.41(11) . . . . ?
C8 C9 C10 C6 -0.07(18) . . . . ?
C14 C9 C10 C6 -179.26(15) . . . . ?
Fe1 C9 C10 C6 59.81(11) . . . . ?
C8 C9 C10 S1 -171.28(12) . . . . ?
C14 C9 C10 S1 9.5(3) . . . . ?
Fe1 C9 C10 S1 -111.40(14) . . . . ?
C8 C9 C10 Fe1 -59.88(11) . . . . ?
C14 C9 C10 Fe1 120.93(17) . . . . ?
C6 C10 S1 O12 -158.02(13) . . . . ?
C9 C10 S1 O12 12.26(18) . . . . ?
Fe1 C10 S1 O12 -74.85(11) . . . . ?
C6 C10 S1 O11 -20.27(16) . . . . ?
C9 C10 S1 O11 150.00(14) . . . . ?
Fe1 C10 S1 O11 62.90(11) . . . . ?
C6 C10 S1 F13 89.14(14) . . . . ?
C9 C10 S1 F13 -100.59(15) . . . . ?
Fe1 C10 S1 F13 172.31(8) . . . . ?
C8 C9 C14 C15 46.5(2) . . . . ?
C10 C9 C14 C15 -134.47(18) . . . . ?
Fe1 C9 C14 C15 -43.2(2) . . . . ?
C8 C9 C14 C19 -129.55(17) . . . . ?
C10 C9 C14 C19 49.5(2) . . . . ?
Fe1 C9 C14 C19 140.73(14) . . . . ?
C19 C14 C15 C16 -1.3(2) . . . . ?
C9 C14 C15 C16 -177.47(15) . . . . ?
C14 C15 C16 O20 -178.03(15) . . . . ?
C14 C15 C16 C17 1.1(3) . . . . ?
O20 C16 C17 C18 178.78(16) . . . . ?
C15 C16 C17 C18 -0.4(3) . . . . ?
C16 C17 C18 C19 0.0(3) . . . . ?
C17 C18 C19 O22 176.90(16) . . . . ?
C17 C18 C19 C14 -0.2(3) . . . . ?
C15 C14 C19 O22 -176.47(14) . . . . ?
C9 C14 C19 O22 -0.5(2) . . . . ?
C15 C14 C19 C18 0.9(2) . . . . ?
C9 C14 C19 C18 176.88(15) . . . . ?
C15 C16 O20 C21 4.5(2) . . . . ?
C17 C16 O20 C21 -174.71(17) . . . . ?
C18 C19 O22 C23 11.6(2) . . . . ?
C14 C19 O22 C23 -171.22(15) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


####################################################################### 
# 
# 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_WE17851
_database_code_depnum_ccdc_archive 'CCDC 2189759'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;ISCR
France
;
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2022-09-25 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 11 janvier 2022                                          #
#------------------------------------------------------------------------------#


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H18 F2 Fe O2 S Si'
_chemical_formula_sum            'C14 H18 F2 Fe O2 S Si'
_chemical_formula_weight         372.28
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
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                   9.6910(16)
_cell_length_b                   11.7554(19)
_cell_length_c                   13.9616(19)
_cell_angle_alpha                90
_cell_angle_beta                 96.089(6)
_cell_angle_gamma                90
_cell_volume                     1581.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9882
_cell_measurement_theta_min      2.2702
_cell_measurement_theta_max      27.4451
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      0.0641400
_diffrn_orient_matrix_UB_21      0.0792976
_diffrn_orient_matrix_UB_31      -0.0191589
_diffrn_orient_matrix_UB_12      0.0633647
_diffrn_orient_matrix_UB_22      -0.0420398
_diffrn_orient_matrix_UB_32      0.0381315
_diffrn_orient_matrix_UB_13      0.0227205
_diffrn_orient_matrix_UB_23      -0.0238556
_diffrn_orient_matrix_UB_33      -0.0640564


#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.100
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             768
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.182
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.802
_exptl_absorpt_correction_T_max  0.889

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

# Software                   : BIS V6.2.15/2021-03-15 && APEX4 2021.10-0       #
# Number of scans            :        3                                        #
# Total number of frames [*] :      431                                        #
# Total length of scans  [*] :   431.00 (deg.)                                 #
# Rotation speed         [*] :     4.00 sec./deg.                              #
# Total exposition time  [*] :         28.7 min.                               #
#                                                                              #
#  [*] fast scan not included                                                  #
#                                                                              #
#    Scan  Time(s) Width DX(mm) Frames Range 2Theta  Omega    Phi    Chi  T(K) #
#..............................................................................#
#                                                                              #
#  1 Fast     1.0  1.00    34.0   180  180.0    0.0    0.0    0.0   54.7 150.0 #
#  2 Phi      4.0  1.00    34.0   200  200.0    0.1  270.3  140.0   24.0 150.0 #
#  3 Phi      4.0  1.00    34.0   231  231.0    0.1    2.4  216.5  -44.5 150.0 #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.00
_diffrn_source_voltage           50.00
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0282
_diffrn_reflns_av_r_equivalents  0.0415
_diffrn_reflns_number            24512
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.270
_diffrn_reflns_theta_max         27.455
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_reflns_number_total             3597
_reflns_number_gt                3337
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2021)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0288P)²+0.9429P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         3597
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0258
_refine_ls_wR_factor_ref         0.0661
_refine_ls_wR_factor_gt          0.0643
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.062

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'
F F 0.0171 0.0103 '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'
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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.63848(2) 0.77245(2) 0.64994(2) 0.01676(7) Uani 1 1 d . . . . .
C1 C 0.5561(3) 0.82393(17) 0.51576(13) 0.0458(5) Uani 1 1 d . . . . .
H1 H 0.531228 0.775382 0.462311 0.055 Uiso 1 1 calc R U . . .
C2 C 0.6884(2) 0.8745(2) 0.54127(17) 0.0516(6) Uani 1 1 d . . . . .
H2 H 0.767997 0.865620 0.507703 0.062 Uiso 1 1 calc R U . . .
C3 C 0.6806(2) 0.93908(16) 0.62406(17) 0.0498(6) Uani 1 1 d . . . . .
H3 H 0.753997 0.982072 0.656859 0.060 Uiso 1 1 calc R U . . .
C4 C 0.5471(3) 0.92983(16) 0.65033(15) 0.0464(5) Uani 1 1 d . . . . .
H4 H 0.513728 0.965569 0.704374 0.056 Uiso 1 1 calc R U . . .
C5 C 0.46959(19) 0.85919(17) 0.58417(15) 0.0407(5) Uani 1 1 d . . . . .
H5 H 0.374949 0.838810 0.585501 0.049 Uiso 1 1 calc R U . . .
C6 C 0.65069(14) 0.59795(12) 0.64760(10) 0.0185(3) Uani 1 1 d . . . . .
H6 H 0.616443 0.548726 0.596565 0.022 Uiso 1 1 calc R U . . .
C7 C 0.78747(15) 0.64433(12) 0.65881(11) 0.0200(3) Uani 1 1 d . . . . .
C8 C 0.79561(14) 0.71159(12) 0.74246(11) 0.0188(3) Uani 1 1 d . . . . .
C9 C 0.66598(14) 0.70784(12) 0.78320(10) 0.0164(3) Uani 1 1 d . . . . .
C10 C 0.57116(14) 0.63486(11) 0.72299(10) 0.0163(3) Uani 1 1 d . . . . .
C11 C 0.90116(17) 0.62608(16) 0.59590(12) 0.0297(3) Uani 1 1 d . . . . .
H11A H 0.962674 0.692465 0.599958 0.044 Uiso 1 1 calc R U . . .
H11B H 0.860906 0.615603 0.529086 0.044 Uiso 1 1 calc R U . . .
H11C H 0.954409 0.558207 0.617447 0.044 Uiso 1 1 calc R U . . .
F12 F 0.91026(9) 0.76619(8) 0.78054(7) 0.0275(2) Uani 1 1 d . . . . .
S1 S 0.63267(4) 0.77846(3) 0.88565(3) 0.02288(10) Uani 1 1 d . . . . .
O13 O 0.73901(15) 0.85684(11) 0.91530(9) 0.0400(3) Uani 1 1 d . . . . .
O14 O 0.49167(14) 0.80843(15) 0.88312(10) 0.0508(4) Uani 1 1 d . . . . .
F15 F 0.65268(13) 0.67993(10) 0.96141(7) 0.0404(3) Uani 1 1 d . . . . .
Si1 Si 0.39342(4) 0.57705(3) 0.73834(3) 0.01967(10) Uani 1 1 d . . . . .
C16 C 0.40982(19) 0.48909(16) 0.85034(12) 0.0323(4) Uani 1 1 d . . . . .
H16A H 0.317958 0.461548 0.862795 0.048 Uiso 1 1 calc R U . . .
H16B H 0.449296 0.535477 0.904816 0.048 Uiso 1 1 calc R U . . .
H16C H 0.470804 0.424092 0.842191 0.048 Uiso 1 1 calc R U . . .
C17 C 0.25610(19) 0.68737(18) 0.74340(19) 0.0455(5) Uani 1 1 d . . . . .
H17A H 0.238317 0.724421 0.680423 0.068 Uiso 1 1 calc R U . . .
H17B H 0.287162 0.744274 0.792291 0.068 Uiso 1 1 calc R U . . .
H17C H 0.170651 0.651386 0.760152 0.068 Uiso 1 1 calc R U . . .
C18 C 0.34432(18) 0.48437(15) 0.63201(12) 0.0300(4) Uani 1 1 d . . . . .
H18A H 0.253976 0.449181 0.638067 0.045 Uiso 1 1 calc R U . . .
H18B H 0.414518 0.424864 0.628879 0.045 Uiso 1 1 calc R U . . .
H18C H 0.338608 0.530283 0.573139 0.045 Uiso 1 1 calc R U . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_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 C9 2.0011(14) . ?
Fe1 C8 2.0203(14) . ?
Fe1 C2 2.0321(18) . ?
Fe1 C3 2.0408(18) . ?
Fe1 C1 2.0484(17) . ?
Fe1 C4 2.0513(18) . ?
Fe1 C10 2.0549(14) . ?
Fe1 C6 2.0551(15) . ?
Fe1 C5 2.0599(17) . ?
Fe1 C7 2.0809(15) . ?
C1 C5 1.399(3) . ?
C1 C2 1.423(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.392(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.400(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.4264(19) . ?
C6 C10 1.4360(19) . ?
C6 H6 0.9500 . ?
C7 C8 1.406(2) . ?
C7 C11 1.496(2) . ?
C8 F12 1.3431(16) . ?
C8 C9 1.434(2) . ?
C9 C10 1.4571(19) . ?
C9 S1 1.7138(14) . ?
C10 Si1 1.8849(14) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
S1 O14 1.4079(14) . ?
S1 O13 1.4114(13) . ?
S1 F15 1.5667(11) . ?
Si1 C18 1.8621(17) . ?
Si1 C17 1.8648(19) . ?
Si1 C16 1.8673(18) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C9 Fe1 C8 41.77(6) . . ?
C9 Fe1 C2 154.08(9) . . ?
C8 Fe1 C2 117.61(8) . . ?
C9 Fe1 C3 121.30(8) . . ?
C8 Fe1 C3 107.57(7) . . ?
C2 Fe1 C3 39.97(10) . . ?
C9 Fe1 C1 164.37(8) . . ?
C8 Fe1 C1 152.08(8) . . ?
C2 Fe1 C1 40.83(10) . . ?
C3 Fe1 C1 67.69(8) . . ?
C9 Fe1 C4 110.78(7) . . ?
C8 Fe1 C4 127.87(8) . . ?
C2 Fe1 C4 66.84(9) . . ?
C3 Fe1 C4 39.57(10) . . ?
C1 Fe1 C4 67.01(8) . . ?
C9 Fe1 C10 42.08(5) . . ?
C8 Fe1 C10 70.21(6) . . ?
C2 Fe1 C10 161.48(9) . . ?
C3 Fe1 C10 157.40(9) . . ?
C1 Fe1 C10 124.95(8) . . ?
C4 Fe1 C10 123.28(8) . . ?
C9 Fe1 C6 68.52(6) . . ?
C8 Fe1 C6 67.42(6) . . ?
C2 Fe1 C6 123.95(8) . . ?
C3 Fe1 C6 160.43(9) . . ?
C1 Fe1 C6 107.33(7) . . ?
C4 Fe1 C6 157.80(8) . . ?
C10 Fe1 C6 40.90(5) . . ?
C9 Fe1 C5 128.57(7) . . ?
C8 Fe1 C5 165.85(8) . . ?
C2 Fe1 C5 67.41(8) . . ?
C3 Fe1 C5 67.06(8) . . ?
C1 Fe1 C5 39.81(9) . . ?
C4 Fe1 C5 39.82(9) . . ?
C10 Fe1 C5 109.38(7) . . ?
C6 Fe1 C5 122.10(7) . . ?
C9 Fe1 C7 69.32(6) . . ?
C8 Fe1 C7 40.05(6) . . ?
C2 Fe1 C7 104.65(8) . . ?
C3 Fe1 C7 123.69(8) . . ?
C1 Fe1 C7 117.96(8) . . ?
C4 Fe1 C7 161.72(8) . . ?
C10 Fe1 C7 69.86(6) . . ?
C6 Fe1 C7 40.34(5) . . ?
C5 Fe1 C7 153.93(8) . . ?
C5 C1 C2 107.13(18) . . ?
C5 C1 Fe1 70.54(10) . . ?
C2 C1 Fe1 68.97(11) . . ?
C5 C1 H1 126.4 . . ?
C2 C1 H1 126.4 . . ?
Fe1 C1 H1 125.6 . . ?
C3 C2 C1 107.98(19) . . ?
C3 C2 Fe1 70.36(11) . . ?
C1 C2 Fe1 70.20(11) . . ?
C3 C2 H2 126.0 . . ?
C1 C2 H2 126.0 . . ?
Fe1 C2 H2 125.0 . . ?
C4 C3 C2 108.16(18) . . ?
C4 C3 Fe1 70.62(11) . . ?
C2 C3 Fe1 69.68(11) . . ?
C4 C3 H3 125.9 . . ?
C2 C3 H3 125.9 . . ?
Fe1 C3 H3 125.4 . . ?
C3 C4 C5 108.82(19) . . ?
C3 C4 Fe1 69.81(11) . . ?
C5 C4 Fe1 70.42(11) . . ?
C3 C4 H4 125.6 . . ?
C5 C4 H4 125.6 . . ?
Fe1 C4 H4 125.8 . . ?
C1 C5 C4 107.91(19) . . ?
C1 C5 Fe1 69.65(10) . . ?
C4 C5 Fe1 69.76(10) . . ?
C1 C5 H5 126.0 . . ?
C4 C5 H5 126.0 . . ?
Fe1 C5 H5 126.1 . . ?
C7 C6 C10 111.64(12) . . ?
C7 C6 Fe1 70.80(8) . . ?
C10 C6 Fe1 69.54(8) . . ?
C7 C6 H6 124.2 . . ?
C10 C6 H6 124.2 . . ?
Fe1 C6 H6 127.1 . . ?
C8 C7 C6 106.01(12) . . ?
C8 C7 C11 126.07(14) . . ?
C6 C7 C11 127.93(14) . . ?
C8 C7 Fe1 67.65(8) . . ?
C6 C7 Fe1 68.86(8) . . ?
C11 C7 Fe1 128.22(11) . . ?
F12 C8 C7 124.67(13) . . ?
F12 C8 C9 125.49(13) . . ?
C7 C8 C9 109.76(12) . . ?
F12 C8 Fe1 128.29(10) . . ?
C7 C8 Fe1 72.30(8) . . ?
C9 C8 Fe1 68.40(8) . . ?
C8 C9 C10 108.34(12) . . ?
C8 C9 S1 124.53(11) . . ?
C10 C9 S1 127.13(11) . . ?
C8 C9 Fe1 69.83(8) . . ?
C10 C9 Fe1 70.94(8) . . ?
S1 C9 Fe1 125.02(8) . . ?
C6 C10 C9 104.25(12) . . ?
C6 C10 Si1 122.85(10) . . ?
C9 C10 Si1 132.42(11) . . ?
C6 C10 Fe1 69.56(8) . . ?
C9 C10 Fe1 66.98(8) . . ?
Si1 C10 Fe1 133.02(7) . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O14 S1 O13 121.37(10) . . ?
O14 S1 F15 104.61(9) . . ?
O13 S1 F15 104.50(8) . . ?
O14 S1 C9 111.62(8) . . ?
O13 S1 C9 111.39(8) . . ?
F15 S1 C9 100.64(7) . . ?
C18 Si1 C17 108.30(10) . . ?
C18 Si1 C16 109.60(8) . . ?
C17 Si1 C16 110.55(10) . . ?
C18 Si1 C10 106.24(7) . . ?
C17 Si1 C10 114.71(8) . . ?
C16 Si1 C10 107.29(7) . . ?
Si1 C16 H16A 109.5 . . ?
Si1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
Si1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
Si1 C17 H17A 109.5 . . ?
Si1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
Si1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
Si1 C18 H18A 109.5 . . ?
Si1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
Si1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C5 C1 C2 C3 0.0(2) . . . . ?
Fe1 C1 C2 C3 -60.50(13) . . . . ?
C5 C1 C2 Fe1 60.52(13) . . . . ?
C1 C2 C3 C4 0.0(2) . . . . ?
Fe1 C2 C3 C4 -60.41(13) . . . . ?
C1 C2 C3 Fe1 60.40(13) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
Fe1 C3 C4 C5 -59.83(13) . . . . ?
C2 C3 C4 Fe1 59.81(13) . . . . ?
C2 C1 C5 C4 0.0(2) . . . . ?
Fe1 C1 C5 C4 59.49(13) . . . . ?
C2 C1 C5 Fe1 -59.52(13) . . . . ?
C3 C4 C5 C1 0.0(2) . . . . ?
Fe1 C4 C5 C1 -59.42(13) . . . . ?
C3 C4 C5 Fe1 59.45(13) . . . . ?
C10 C6 C7 C8 0.09(17) . . . . ?
Fe1 C6 C7 C8 57.65(10) . . . . ?
C10 C6 C7 C11 179.78(15) . . . . ?
Fe1 C6 C7 C11 -122.66(16) . . . . ?
C10 C6 C7 Fe1 -57.56(10) . . . . ?
C6 C7 C8 F12 176.82(13) . . . . ?
C11 C7 C8 F12 -2.9(2) . . . . ?
Fe1 C7 C8 F12 -124.75(14) . . . . ?
C6 C7 C8 C9 -0.11(16) . . . . ?
C11 C7 C8 C9 -179.81(14) . . . . ?
Fe1 C7 C8 C9 58.31(10) . . . . ?
C6 C7 C8 Fe1 -58.42(10) . . . . ?
C11 C7 C8 Fe1 121.88(16) . . . . ?
F12 C8 C9 C10 -176.81(13) . . . . ?
C7 C8 C9 C10 0.10(16) . . . . ?
Fe1 C8 C9 C10 60.77(10) . . . . ?
F12 C8 C9 S1 3.1(2) . . . . ?
C7 C8 C9 S1 -179.97(11) . . . . ?
Fe1 C8 C9 S1 -119.30(11) . . . . ?
F12 C8 C9 Fe1 122.42(14) . . . . ?
C7 C8 C9 Fe1 -60.67(11) . . . . ?
C7 C6 C10 C9 -0.03(16) . . . . ?
Fe1 C6 C10 C9 -58.32(9) . . . . ?
C7 C6 C10 Si1 -172.96(10) . . . . ?
Fe1 C6 C10 Si1 128.76(10) . . . . ?
C7 C6 C10 Fe1 58.29(10) . . . . ?
C8 C9 C10 C6 -0.04(15) . . . . ?
S1 C9 C10 C6 -179.97(11) . . . . ?
Fe1 C9 C10 C6 60.04(9) . . . . ?
C8 C9 C10 Si1 171.90(11) . . . . ?
S1 C9 C10 Si1 -8.0(2) . . . . ?
Fe1 C9 C10 Si1 -128.02(12) . . . . ?
C8 C9 C10 Fe1 -60.08(10) . . . . ?
S1 C9 C10 Fe1 119.99(12) . . . . ?
C8 C9 S1 O14 149.88(14) . . . . ?
C10 C9 S1 O14 -30.21(16) . . . . ?
Fe1 C9 S1 O14 61.53(13) . . . . ?
C8 C9 S1 O13 10.71(15) . . . . ?
C10 C9 S1 O13 -169.37(13) . . . . ?
Fe1 C9 S1 O13 -77.63(11) . . . . ?
C8 C9 S1 F15 -99.60(13) . . . . ?
C10 C9 S1 F15 80.32(13) . . . . ?
Fe1 C9 S1 F15 172.05(9) . . . . ?
C6 C10 Si1 C18 -6.69(14) . . . . ?
C9 C10 Si1 C18 -177.38(13) . . . . ?
Fe1 C10 Si1 C18 85.25(11) . . . . ?
C6 C10 Si1 C17 -126.30(14) . . . . ?
C9 C10 Si1 C17 63.01(17) . . . . ?
Fe1 C10 Si1 C17 -34.36(14) . . . . ?
C6 C10 Si1 C16 110.48(13) . . . . ?
C9 C10 Si1 C16 -60.22(15) . . . . ?
Fe1 C10 Si1 C16 -157.58(10) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


####################################################################### 
# 
# 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_WE17861
_database_code_depnum_ccdc_archive 'CCDC 2189760'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;ISCR
France
;
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2022-09-25 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 11 janvier 2022                                          #
#------------------------------------------------------------------------------#


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C11 H10 F2 Fe O2 S'
_chemical_formula_sum            'C11 H10 F2 Fe O2 S'
_chemical_formula_weight         300.10
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration rm/ad/rmad/syn/unk/.

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
_space_group_IT_number           33
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'
'-x, -y, z+1/2'

_cell_length_a                   13.125(3)
_cell_length_b                   13.589(3)
_cell_length_c                   6.2890(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1121.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6599
_cell_measurement_theta_min      2.9981
_cell_measurement_theta_max      27.4557
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      -0.0215862
_diffrn_orient_matrix_UB_21      0.1148684
_diffrn_orient_matrix_UB_31      0.1078076
_diffrn_orient_matrix_UB_12      0.0376867
_diffrn_orient_matrix_UB_22      -0.0414124
_diffrn_orient_matrix_UB_32      0.0516706
_diffrn_orient_matrix_UB_13      0.0631721
_diffrn_orient_matrix_UB_23      0.0314545
_diffrn_orient_matrix_UB_33      -0.0208657


#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.120
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.777
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             608
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.542
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.587
_exptl_absorpt_correction_T_max  0.831

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

# Software                   : BIS V6.2.15/2021-03-15 && APEX4 2021.10-0       #
# Number of scans            :        3                                        #
# Total number of frames [*] :      127                                        #
# Total length of scans  [*] :   127.00 (deg.)                                 #
# Rotation speed         [*] :    10.00 sec./deg.                              #
# Total exposition time  [*] :         21.2 min.                               #
#                                                                              #
#  [*] fast scan not included                                                  #
#                                                                              #
#    Scan  Time(s) Width DX(mm) Frames Range 2Theta  Omega    Phi    Chi  T(K) #
#..............................................................................#
#                                                                              #
#  1 Fast     1.0  1.00    34.0   180  180.0    0.0    0.0    0.0   54.7 150.0 #
#  2 Fast@    1.0  1.00    34.0   180  180.0    0.0    0.0  180.0   54.7 150.0 #
#  3 Phi     10.0  1.00    34.0   127  127.0    0.1    1.9   24.5  -24.0 150.0 #
#                                                                              #
#  @: attenuated beam                                                          #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.00
_diffrn_source_voltage           50.00
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0311
_diffrn_reflns_av_r_equivalents  0.0251
_diffrn_reflns_number            5297
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         2.998
_diffrn_reflns_theta_max         27.456
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_reflns_number_total             2156
_reflns_number_gt                2084
_reflns_threshold_expression     >2sigma(I)
_reflns_Friedel_coverage         0.551
_reflns_Friedel_fraction_max     0.658
_reflns_Friedel_fraction_full    0.711

_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.
;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2021)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0332P)²+0.3374P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         2156
_refine_ls_number_parameters     156
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0236
_refine_ls_R_factor_gt           0.0225
_refine_ls_wR_factor_ref         0.0605
_refine_ls_wR_factor_gt          0.0598
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.002
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.26(2)

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'
F F 0.0171 0.0103 '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'
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'

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 0.24179(2) 0.50817(2) 0.55611(14) 0.01893(12) Uani 1 1 d . . . . .
C1 C 0.1278(2) 0.4274(3) 0.4214(8) 0.0410(10) Uani 1 1 d . . . . .
H1 H 0.134642 0.363155 0.363380 0.049 Uiso 1 1 calc R U . . .
C2 C 0.1026(2) 0.4499(3) 0.6337(7) 0.0366(9) Uani 1 1 d . . . . .
H2 H 0.089444 0.403846 0.744040 0.044 Uiso 1 1 calc R U . . .
C3 C 0.1005(2) 0.5536(3) 0.6526(6) 0.0323(8) Uani 1 1 d . . . . .
H3 H 0.085685 0.589574 0.778411 0.039 Uiso 1 1 calc R U . . .
C4 C 0.1242(2) 0.5944(2) 0.4533(7) 0.0341(8) Uani 1 1 d . . . . .
H4 H 0.127973 0.662660 0.421389 0.041 Uiso 1 1 calc R U . . .
C5 C 0.1412(3) 0.5170(3) 0.3090(7) 0.0400(9) Uani 1 1 d . . . . .
H5 H 0.158523 0.523547 0.163009 0.048 Uiso 1 1 calc R U . . .
C6 C 0.3833(2) 0.51810(19) 0.4339(5) 0.0194(6) Uani 1 1 d . . . . .
C7 C 0.37013(17) 0.42916(18) 0.5536(6) 0.0204(5) Uani 1 1 d . . . . .
C8 C 0.3460(2) 0.4574(2) 0.7671(5) 0.0249(6) Uani 1 1 d . . . . .
H8 H 0.333160 0.414498 0.883262 0.030 Uiso 1 1 calc R U . . .
C9 C 0.3451(2) 0.5619(2) 0.7720(5) 0.0251(6) Uani 1 1 d . . . . .
H9 H 0.331253 0.600622 0.894398 0.030 Uiso 1 1 calc R U . . .
C10 C 0.36791(17) 0.60004(19) 0.5675(6) 0.0218(6) Uani 1 1 d . . . . .
F11 F 0.41059(13) 0.52291(13) 0.2291(3) 0.0264(4) Uani 1 1 d . . . . .
C12 C 0.3754(2) 0.7061(2) 0.4994(5) 0.0287(8) Uani 1 1 d . . . . .
H12A H 0.443295 0.731450 0.533611 0.043 Uiso 1 1 calc R U . . .
H12B H 0.323758 0.744912 0.574500 0.043 Uiso 1 1 calc R U . . .
H12C H 0.363864 0.710813 0.345768 0.043 Uiso 1 1 calc R U . . .
S1 S 0.37136(5) 0.31230(5) 0.45360(13) 0.02609(18) Uani 1 1 d . . . . .
F13 F 0.48460(15) 0.28107(14) 0.5002(4) 0.0441(6) Uani 1 1 d . . . . .
O14 O 0.31145(19) 0.24804(15) 0.5787(5) 0.0404(6) Uani 1 1 d . . . . .
O15 O 0.3635(2) 0.31186(16) 0.2304(4) 0.0361(6) Uani 1 1 d . . . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_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 1.997(2) . ?
Fe1 C6 2.015(3) . ?
Fe1 C8 2.027(3) . ?
Fe1 C1 2.040(3) . ?
Fe1 C4 2.043(3) . ?
Fe1 C3 2.046(3) . ?
Fe1 C5 2.043(4) . ?
Fe1 C2 2.050(3) . ?
Fe1 C9 2.053(3) . ?
Fe1 C10 2.074(2) . ?
C1 C2 1.410(6) . ?
C1 C5 1.419(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.415(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.405(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.407(6) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 F11 1.339(4) . ?
C6 C10 1.409(4) . ?
C6 C7 1.434(4) . ?
C7 C8 1.432(5) . ?
C7 S1 1.708(3) . ?
C8 C9 1.420(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.418(5) . ?
C9 H9 0.9500 . ?
C10 C12 1.506(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
S1 O15 1.408(3) . ?
S1 O14 1.414(2) . ?
S1 F13 1.573(2) . ?

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 C6 41.88(11) . . ?
C7 Fe1 C8 41.69(14) . . ?
C6 Fe1 C8 69.52(12) . . ?
C7 Fe1 C1 109.01(13) . . ?
C6 Fe1 C1 123.63(16) . . ?
C8 Fe1 C1 125.72(15) . . ?
C7 Fe1 C4 160.54(17) . . ?
C6 Fe1 C4 122.52(14) . . ?
C8 Fe1 C4 155.83(15) . . ?
C1 Fe1 C4 67.86(15) . . ?
C7 Fe1 C3 158.23(14) . . ?
C6 Fe1 C3 158.15(13) . . ?
C8 Fe1 C3 121.35(14) . . ?
C1 Fe1 C3 67.74(15) . . ?
C4 Fe1 C3 40.18(15) . . ?
C7 Fe1 C5 124.78(16) . . ?
C6 Fe1 C5 107.57(15) . . ?
C8 Fe1 C5 162.62(14) . . ?
C1 Fe1 C5 40.68(17) . . ?
C4 Fe1 C5 40.29(16) . . ?
C3 Fe1 C5 67.80(16) . . ?
C7 Fe1 C2 123.07(13) . . ?
C6 Fe1 C2 159.77(13) . . ?
C8 Fe1 C2 108.31(14) . . ?
C1 Fe1 C2 40.32(17) . . ?
C4 Fe1 C2 67.89(15) . . ?
C3 Fe1 C2 40.42(15) . . ?
C5 Fe1 C2 68.16(16) . . ?
C7 Fe1 C9 68.87(13) . . ?
C6 Fe1 C9 67.63(12) . . ?
C8 Fe1 C9 40.73(12) . . ?
C1 Fe1 C9 161.89(17) . . ?
C4 Fe1 C9 120.28(14) . . ?
C3 Fe1 C9 107.16(14) . . ?
C5 Fe1 C9 155.38(14) . . ?
C2 Fe1 C9 124.64(15) . . ?
C7 Fe1 C10 69.57(10) . . ?
C6 Fe1 C10 40.29(11) . . ?
C8 Fe1 C10 69.11(12) . . ?
C1 Fe1 C10 157.43(17) . . ?
C4 Fe1 C10 105.58(12) . . ?
C3 Fe1 C10 122.07(13) . . ?
C5 Fe1 C10 120.44(15) . . ?
C2 Fe1 C10 159.27(14) . . ?
C9 Fe1 C10 40.19(13) . . ?
C2 C1 C5 108.3(3) . . ?
C2 C1 Fe1 70.2(2) . . ?
C5 C1 Fe1 69.8(2) . . ?
C2 C1 H1 125.8 . . ?
C5 C1 H1 125.8 . . ?
Fe1 C1 H1 125.8 . . ?
C1 C2 C3 107.5(3) . . ?
C1 C2 Fe1 69.5(2) . . ?
C3 C2 Fe1 69.65(16) . . ?
C1 C2 H2 126.3 . . ?
C3 C2 H2 126.3 . . ?
Fe1 C2 H2 126.2 . . ?
C4 C3 C2 108.3(3) . . ?
C4 C3 Fe1 69.80(18) . . ?
C2 C3 Fe1 69.93(16) . . ?
C4 C3 H3 125.8 . . ?
C2 C3 H3 125.9 . . ?
Fe1 C3 H3 126.0 . . ?
C3 C4 C5 108.4(3) . . ?
C3 C4 Fe1 70.02(19) . . ?
C5 C4 Fe1 69.82(19) . . ?
C3 C4 H4 125.8 . . ?
C5 C4 H4 125.8 . . ?
Fe1 C4 H4 125.9 . . ?
C4 C5 C1 107.5(4) . . ?
C4 C5 Fe1 69.9(2) . . ?
C1 C5 Fe1 69.6(2) . . ?
C4 C5 H5 126.2 . . ?
C1 C5 H5 126.2 . . ?
Fe1 C5 H5 125.9 . . ?
F11 C6 C10 125.0(3) . . ?
F11 C6 C7 125.3(3) . . ?
C10 C6 C7 109.6(3) . . ?
F11 C6 Fe1 128.1(2) . . ?
C10 C6 Fe1 72.14(15) . . ?
C7 C6 Fe1 68.42(14) . . ?
C8 C7 C6 107.0(2) . . ?
C8 C7 S1 126.6(2) . . ?
C6 C7 S1 126.1(3) . . ?
C8 C7 Fe1 70.26(16) . . ?
C6 C7 Fe1 69.69(14) . . ?
S1 C7 Fe1 120.71(14) . . ?
C9 C8 C7 106.9(2) . . ?
C9 C8 Fe1 70.63(16) . . ?
C7 C8 Fe1 68.06(16) . . ?
C9 C8 H8 126.6 . . ?
C7 C8 H8 126.6 . . ?
Fe1 C8 H8 126.3 . . ?
C10 C9 C8 110.1(3) . . ?
C10 C9 Fe1 70.71(17) . . ?
C8 C9 Fe1 68.64(16) . . ?
C10 C9 H9 124.9 . . ?
C8 C9 H9 124.9 . . ?
Fe1 C9 H9 127.3 . . ?
C6 C10 C9 106.4(2) . . ?
C6 C10 C12 125.2(3) . . ?
C9 C10 C12 128.4(3) . . ?
C6 C10 Fe1 67.57(15) . . ?
C9 C10 Fe1 69.10(16) . . ?
C12 C10 Fe1 128.14(19) . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O15 S1 O14 120.76(16) . . ?
O15 S1 F13 104.71(14) . . ?
O14 S1 F13 104.78(14) . . ?
O15 S1 C7 111.74(16) . . ?
O14 S1 C7 111.35(15) . . ?
F13 S1 C7 101.03(12) . . ?

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
C5 C1 C2 C3 0.0(3) . . . . ?
Fe1 C1 C2 C3 59.5(2) . . . . ?
C5 C1 C2 Fe1 -59.6(2) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
Fe1 C2 C3 C4 59.5(2) . . . . ?
C1 C2 C3 Fe1 -59.4(2) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
Fe1 C3 C4 C5 59.5(2) . . . . ?
C2 C3 C4 Fe1 -59.5(2) . . . . ?
C3 C4 C5 C1 0.0(4) . . . . ?
Fe1 C4 C5 C1 59.6(2) . . . . ?
C3 C4 C5 Fe1 -59.6(2) . . . . ?
C2 C1 C5 C4 0.0(4) . . . . ?
Fe1 C1 C5 C4 -59.8(2) . . . . ?
C2 C1 C5 Fe1 59.9(2) . . . . ?
F11 C6 C7 C8 177.1(2) . . . . ?
C10 C6 C7 C8 -0.1(3) . . . . ?
Fe1 C6 C7 C8 -60.67(18) . . . . ?
F11 C6 C7 S1 -8.4(4) . . . . ?
C10 C6 C7 S1 174.42(18) . . . . ?
Fe1 C6 C7 S1 113.8(2) . . . . ?
F11 C6 C7 Fe1 -122.2(3) . . . . ?
C10 C6 C7 Fe1 60.6(2) . . . . ?
C6 C7 C8 C9 0.0(3) . . . . ?
S1 C7 C8 C9 -174.43(19) . . . . ?
Fe1 C7 C8 C9 -60.27(18) . . . . ?
C6 C7 C8 Fe1 60.31(18) . . . . ?
S1 C7 C8 Fe1 -114.2(2) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
Fe1 C8 C9 C10 -58.61(19) . . . . ?
C7 C8 C9 Fe1 58.62(18) . . . . ?
F11 C6 C10 C9 -177.1(2) . . . . ?
C7 C6 C10 C9 0.1(3) . . . . ?
Fe1 C6 C10 C9 58.42(18) . . . . ?
F11 C6 C10 C12 2.7(4) . . . . ?
C7 C6 C10 C12 179.9(2) . . . . ?
Fe1 C6 C10 C12 -121.8(3) . . . . ?
F11 C6 C10 Fe1 124.4(3) . . . . ?
C7 C6 C10 Fe1 -58.32(19) . . . . ?
C8 C9 C10 C6 -0.1(3) . . . . ?
Fe1 C9 C10 C6 -57.45(18) . . . . ?
C8 C9 C10 C12 -179.9(3) . . . . ?
Fe1 C9 C10 C12 122.7(3) . . . . ?
C8 C9 C10 Fe1 57.38(19) . . . . ?
C8 C7 S1 O15 159.7(2) . . . . ?
C6 C7 S1 O15 -13.7(3) . . . . ?
Fe1 C7 S1 O15 72.5(2) . . . . ?
C8 C7 S1 O14 21.4(3) . . . . ?
C6 C7 S1 O14 -152.1(2) . . . . ?
Fe1 C7 S1 O14 -65.9(3) . . . . ?
C8 C7 S1 F13 -89.4(2) . . . . ?
C6 C7 S1 F13 97.1(2) . . . . ?
Fe1 C7 S1 F13 -176.68(19) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


####################################################################### 
# 
# 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_WE18391
_database_code_depnum_ccdc_archive 'CCDC 2189762'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;ISCR
France
;
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2022-09-25 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 07 fevrier 2022                                          #
#------------------------------------------------------------------------------#


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H19 Cl F Fe N O2 S2'
_chemical_formula_sum            'C19 H19 Cl F Fe N O2 S2'
_chemical_formula_weight         467.77
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
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                   7.9543(7)
_cell_length_b                   19.0071(13)
_cell_length_c                   12.9401(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.730(4)
_cell_angle_gamma                90
_cell_volume                     1946.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4162
_cell_measurement_theta_min      2.6638
_cell_measurement_theta_max      26.9422
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      -0.0465195
_diffrn_orient_matrix_UB_21      0.1163833
_diffrn_orient_matrix_UB_31      -0.0159717
_diffrn_orient_matrix_UB_12      -0.0432484
_diffrn_orient_matrix_UB_22      -0.0136251
_diffrn_orient_matrix_UB_32      0.0266823
_diffrn_orient_matrix_UB_13      0.0307162
_diffrn_orient_matrix_UB_23      0.0296026
_diffrn_orient_matrix_UB_33      0.0649032


#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.590
_exptl_crystal_size_mid          0.480
_exptl_crystal_size_min          0.110
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             960
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.150
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.697
_exptl_absorpt_correction_T_max  0.881

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

# Software                   : BIS 2014.5.0.0/23-May-2014 && APEX2_2014.11-0   #
# Number of scans            :        3                                        #
# Total number of frames     :      290                                        #
# Total length of scans      :   290.00 (deg.)                                 #
# Rotation speed             :     8.00 sec./deg.                              #
# Total exposition time      :         38.7 min.                               #
#                                                                              #
#    Scan  Time(s) Width DX(mm) Frames Range 2Theta  Omega    Phi    Chi  T(K) #
#..............................................................................#
#                                                                              #
#  1 Omega    8.0  1.00    35.0    94   94.0  344.0  254.1  248.9   23.5 150.0 #
#  2 Omega    8.0  1.00    35.0    93   93.0  344.0  341.0  228.9  -23.3 150.0 #
#  3 Omega    8.0  1.00    35.0   103  103.0   16.0   14.1  116.6  -46.3 150.0 #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'APEXII Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 CCD-LDI-APEX2
_diffrn_detector_area_resol_mean 8.33
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_source_current           30.00
_diffrn_source_voltage           50.00
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0431
_diffrn_reflns_av_r_equivalents  0.0344
_diffrn_reflns_number            13204
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.664
_diffrn_reflns_theta_max         27.510
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.978
_reflns_number_total             4379
_reflns_number_gt                3591
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2021)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0626P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         4379
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0979
_refine_ls_wR_factor_gt          0.0905
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_restrained_S_all      0.961
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.071

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'
Cl Cl 0.1484 0.1585 '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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.46399(4) 0.73443(2) 0.66567(2) 0.01651(11) Uani 1 1 d . . . . .
Cl1 Cl 0.80620(7) 0.81122(3) 0.80461(4) 0.02272(14) Uani 1 1 d . . . . .
C1 C 0.3080(3) 0.70071(14) 0.77444(18) 0.0299(6) Uani 1 1 d . . . . .
H1 H 0.337756 0.670352 0.831677 0.036 Uiso 1 1 calc R U . . .
C2 C 0.3203(3) 0.77463(15) 0.7756(2) 0.0349(7) Uani 1 1 d . . . . .
H2 H 0.360412 0.802745 0.833590 0.042 Uiso 1 1 calc R U . . .
C3 C 0.2623(3) 0.79976(14) 0.6753(2) 0.0329(6) Uani 1 1 d . . . . .
H3 H 0.256413 0.847660 0.654235 0.040 Uiso 1 1 calc R U . . .
C4 C 0.2146(3) 0.74071(13) 0.6115(2) 0.0266(5) Uani 1 1 d . . . . .
H4 H 0.170963 0.742006 0.540498 0.032 Uiso 1 1 calc R U . . .
C5 C 0.2439(3) 0.67945(13) 0.67348(18) 0.0251(5) Uani 1 1 d . . . . .
H5 H 0.223918 0.632344 0.650969 0.030 Uiso 1 1 calc R U . . .
C6 C 0.7077(3) 0.76508(11) 0.70096(15) 0.0168(4) Uani 1 1 d . . . . .
C7 C 0.6442(3) 0.79624(11) 0.60448(16) 0.0170(4) Uani 1 1 d . . . . .
C8 C 0.5910(3) 0.74073(11) 0.53518(16) 0.0176(4) Uani 1 1 d . . . . .
H8 H 0.545503 0.746856 0.465049 0.021 Uiso 1 1 calc R U . . .
C9 C 0.6159(3) 0.67441(11) 0.58628(15) 0.0167(4) Uani 1 1 d . . . . .
C10 C 0.6900(3) 0.68953(11) 0.69170(15) 0.0165(4) Uani 1 1 d . . . . .
C11 C 0.6308(3) 0.87318(11) 0.57803(16) 0.0200(5) Uani 1 1 d . . . . .
H11A H 0.516687 0.883186 0.543375 0.024 Uiso 1 1 calc R U . . .
H11B H 0.645957 0.901202 0.642776 0.024 Uiso 1 1 calc R U . . .
N12 N 0.7580(2) 0.89429(10) 0.50962(14) 0.0226(4) Uani 1 1 d . . . . .
C13 C 0.7252(3) 0.96619(12) 0.47286(19) 0.0317(6) Uani 1 1 d . . . . .
H13A H 0.728856 0.998166 0.532453 0.048 Uiso 1 1 calc R U . . .
H13B H 0.613330 0.968494 0.433698 0.048 Uiso 1 1 calc R U . . .
H13C H 0.811404 0.980114 0.427780 0.048 Uiso 1 1 calc R U . . .
C14 C 0.9277(3) 0.88883(14) 0.5629(2) 0.0351(6) Uani 1 1 d . . . . .
H14A H 0.939050 0.921308 0.622035 0.053 Uiso 1 1 calc R U . . .
H14B H 1.010735 0.900956 0.514726 0.053 Uiso 1 1 calc R U . . .
H14C H 0.947507 0.840569 0.587863 0.053 Uiso 1 1 calc R U . . .
S1 S 0.73529(8) 0.62949(3) 0.79076(4) 0.02209(15) Uani 1 1 d . . . . .
F15 F 0.92316(19) 0.61152(9) 0.77511(11) 0.0415(4) Uani 1 1 d . . . . .
O16 O 0.7444(2) 0.66179(9) 0.88966(12) 0.0328(4) Uani 1 1 d . . . . .
O17 O 0.6456(3) 0.56609(9) 0.77111(13) 0.0419(5) Uani 1 1 d . . . . .
S2 S 0.56116(7) 0.59334(3) 0.52630(4) 0.02110(14) Uani 1 1 d . . . . .
C18 C 0.7404(3) 0.57717(11) 0.45661(16) 0.0179(4) Uani 1 1 d . . . . .
C19 C 0.7143(3) 0.53887(12) 0.36490(16) 0.0234(5) Uani 1 1 d . . . . .
H19 H 0.603440 0.525008 0.338644 0.028 Uiso 1 1 calc R U . . .
C20 C 0.8517(3) 0.52107(13) 0.31204(17) 0.0292(6) Uani 1 1 d . . . . .
H20 H 0.834620 0.494145 0.250037 0.035 Uiso 1 1 calc R U . . .
C21 C 1.0133(3) 0.54206(13) 0.34853(17) 0.0273(6) Uani 1 1 d . . . . .
H21 H 1.106496 0.529659 0.311750 0.033 Uiso 1 1 calc R U . . .
C22 C 1.0385(3) 0.58133(12) 0.43917(17) 0.0235(5) Uani 1 1 d . . . . .
H22 H 1.149226 0.596265 0.463881 0.028 Uiso 1 1 calc R U . . .
C23 C 0.9032(3) 0.59897(11) 0.49400(16) 0.0205(5) Uani 1 1 d . . . . .
H23 H 0.920893 0.625573 0.556285 0.025 Uiso 1 1 calc R U . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_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 C10 1.988(2) . ?
Fe1 C9 2.016(2) . ?
Fe1 C6 2.032(2) . ?
Fe1 C4 2.040(2) . ?
Fe1 C3 2.042(2) . ?
Fe1 C5 2.050(2) . ?
Fe1 C8 2.056(2) . ?
Fe1 C2 2.059(2) . ?
Fe1 C1 2.069(2) . ?
Fe1 C7 2.071(2) . ?
Cl1 C6 1.724(2) . ?
C1 C2 1.408(4) . ?
C1 C5 1.413(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.417(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.422(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.420(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.428(3) . ?
C6 C10 1.447(3) . ?
C7 C8 1.421(3) . ?
C7 C11 1.503(3) . ?
C8 C9 1.428(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.460(3) . ?
C9 S2 1.760(2) . ?
C10 S1 1.727(2) . ?
C11 N12 1.465(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
N12 C14 1.457(3) . ?
N12 C13 1.462(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
S1 O17 1.4106(19) . ?
S1 O16 1.4148(16) . ?
S1 F15 1.5656(15) . ?
S2 C18 1.788(2) . ?
C18 C19 1.390(3) . ?
C18 C23 1.399(3) . ?
C19 C20 1.388(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.383(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.388(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.388(3) . ?
C22 H22 0.9500 . ?
C23 H23 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 Fe1 C9 42.75(8) . . ?
C10 Fe1 C6 42.17(9) . . ?
C9 Fe1 C6 70.73(8) . . ?
C10 Fe1 C4 156.21(9) . . ?
C9 Fe1 C4 118.03(9) . . ?
C6 Fe1 C4 158.97(9) . . ?
C10 Fe1 C3 162.40(10) . . ?
C9 Fe1 C3 152.80(10) . . ?
C6 Fe1 C3 123.33(9) . . ?
C4 Fe1 C3 40.76(10) . . ?
C10 Fe1 C5 122.35(9) . . ?
C9 Fe1 C5 107.15(9) . . ?
C6 Fe1 C5 159.28(9) . . ?
C4 Fe1 C5 40.61(10) . . ?
C3 Fe1 C5 68.11(10) . . ?
C10 Fe1 C8 69.76(8) . . ?
C9 Fe1 C8 41.04(8) . . ?
C6 Fe1 C8 68.40(8) . . ?
C4 Fe1 C8 104.80(10) . . ?
C3 Fe1 C8 117.89(10) . . ?
C5 Fe1 C8 124.21(9) . . ?
C10 Fe1 C2 126.67(10) . . ?
C9 Fe1 C2 164.67(10) . . ?
C6 Fe1 C2 108.74(9) . . ?
C4 Fe1 C2 68.13(10) . . ?
C3 Fe1 C2 40.42(11) . . ?
C5 Fe1 C2 67.63(10) . . ?
C8 Fe1 C2 153.91(10) . . ?
C10 Fe1 C1 110.20(9) . . ?
C9 Fe1 C1 127.02(10) . . ?
C6 Fe1 C1 124.01(9) . . ?
C4 Fe1 C1 67.86(10) . . ?
C3 Fe1 C1 67.60(11) . . ?
C5 Fe1 C1 40.13(9) . . ?
C8 Fe1 C1 162.57(9) . . ?
C2 Fe1 C1 39.90(11) . . ?
C10 Fe1 C7 70.10(8) . . ?
C9 Fe1 C7 69.71(8) . . ?
C6 Fe1 C7 40.72(8) . . ?
C4 Fe1 C7 121.46(9) . . ?
C3 Fe1 C7 104.84(10) . . ?
C5 Fe1 C7 159.25(9) . . ?
C8 Fe1 C7 40.30(8) . . ?
C2 Fe1 C7 120.45(10) . . ?
C1 Fe1 C7 157.06(9) . . ?
C2 C1 C5 108.3(2) . . ?
C2 C1 Fe1 69.68(13) . . ?
C5 C1 Fe1 69.22(13) . . ?
C2 C1 H1 125.9 . . ?
C5 C1 H1 125.9 . . ?
Fe1 C1 H1 126.8 . . ?
C1 C2 C3 108.1(2) . . ?
C1 C2 Fe1 70.42(13) . . ?
C3 C2 Fe1 69.15(14) . . ?
C1 C2 H2 126.0 . . ?
C3 C2 H2 126.0 . . ?
Fe1 C2 H2 126.0 . . ?
C2 C3 C4 108.0(2) . . ?
C2 C3 Fe1 70.43(14) . . ?
C4 C3 Fe1 69.56(13) . . ?
C2 C3 H3 126.0 . . ?
C4 C3 H3 126.0 . . ?
Fe1 C3 H3 125.6 . . ?
C5 C4 C3 107.5(2) . . ?
C5 C4 Fe1 70.05(13) . . ?
C3 C4 Fe1 69.68(14) . . ?
C5 C4 H4 126.2 . . ?
C3 C4 H4 126.2 . . ?
Fe1 C4 H4 125.6 . . ?
C1 C5 C4 108.1(2) . . ?
C1 C5 Fe1 70.65(13) . . ?
C4 C5 Fe1 69.34(13) . . ?
C1 C5 H5 125.9 . . ?
C4 C5 H5 125.9 . . ?
Fe1 C5 H5 125.7 . . ?
C7 C6 C10 108.44(18) . . ?
C7 C6 Cl1 124.26(16) . . ?
C10 C6 Cl1 127.03(16) . . ?
C7 C6 Fe1 71.11(12) . . ?
C10 C6 Fe1 67.30(12) . . ?
Cl1 C6 Fe1 132.08(11) . . ?
C8 C7 C6 107.50(18) . . ?
C8 C7 C11 124.65(19) . . ?
C6 C7 C11 127.83(19) . . ?
C8 C7 Fe1 69.29(12) . . ?
C6 C7 Fe1 68.17(12) . . ?
C11 C7 Fe1 127.09(15) . . ?
C7 C8 C9 110.14(19) . . ?
C7 C8 Fe1 70.41(12) . . ?
C9 C8 Fe1 67.98(11) . . ?
C7 C8 H8 124.9 . . ?
C9 C8 H8 124.9 . . ?
Fe1 C8 H8 128.3 . . ?
C8 C9 C10 106.47(18) . . ?
C8 C9 S2 123.49(16) . . ?
C10 C9 S2 130.04(16) . . ?
C8 C9 Fe1 70.98(12) . . ?
C10 C9 Fe1 67.60(11) . . ?
S2 C9 Fe1 125.84(11) . . ?
C6 C10 C9 107.43(18) . . ?
C6 C10 S1 125.67(15) . . ?
C9 C10 S1 126.76(17) . . ?
C6 C10 Fe1 70.53(12) . . ?
C9 C10 Fe1 69.65(12) . . ?
S1 C10 Fe1 121.84(11) . . ?
N12 C11 C7 111.51(17) . . ?
N12 C11 H11A 109.3 . . ?
C7 C11 H11A 109.3 . . ?
N12 C11 H11B 109.3 . . ?
C7 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C14 N12 C13 110.33(19) . . ?
C14 N12 C11 110.94(18) . . ?
C13 N12 C11 109.94(18) . . ?
N12 C13 H13A 109.5 . . ?
N12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N12 C14 H14A 109.5 . . ?
N12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O17 S1 O16 120.87(11) . . ?
O17 S1 F15 105.22(11) . . ?
O16 S1 F15 104.37(10) . . ?
O17 S1 C10 111.49(11) . . ?
O16 S1 C10 111.88(10) . . ?
F15 S1 C10 100.33(9) . . ?
C9 S2 C18 101.44(10) . . ?
C19 C18 C23 120.3(2) . . ?
C19 C18 S2 117.51(18) . . ?
C23 C18 S2 122.12(16) . . ?
C20 C19 C18 119.4(2) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C21 C20 C19 120.8(2) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 119.7(2) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
C21 C22 C23 120.5(2) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C22 C23 C18 119.3(2) . . ?
C22 C23 H23 120.3 . . ?
C18 C23 H23 120.3 . . ?

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
C5 C1 C2 C3 0.5(3) . . . . ?
Fe1 C1 C2 C3 59.10(16) . . . . ?
C5 C1 C2 Fe1 -58.62(16) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
Fe1 C2 C3 C4 59.65(16) . . . . ?
C1 C2 C3 Fe1 -59.89(16) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
Fe1 C3 C4 C5 60.11(16) . . . . ?
C2 C3 C4 Fe1 -60.20(17) . . . . ?
C2 C1 C5 C4 -0.5(3) . . . . ?
Fe1 C1 C5 C4 -59.44(16) . . . . ?
C2 C1 C5 Fe1 58.91(16) . . . . ?
C3 C4 C5 C1 0.4(3) . . . . ?
Fe1 C4 C5 C1 60.26(16) . . . . ?
C3 C4 C5 Fe1 -59.88(16) . . . . ?
C10 C6 C7 C8 -1.2(2) . . . . ?
Cl1 C6 C7 C8 173.11(15) . . . . ?
Fe1 C6 C7 C8 -58.28(14) . . . . ?
C10 C6 C7 C11 177.80(19) . . . . ?
Cl1 C6 C7 C11 -7.8(3) . . . . ?
Fe1 C6 C7 C11 120.8(2) . . . . ?
C10 C6 C7 Fe1 57.04(14) . . . . ?
Cl1 C6 C7 Fe1 -128.60(17) . . . . ?
C6 C7 C8 C9 1.3(2) . . . . ?
C11 C7 C8 C9 -177.83(19) . . . . ?
Fe1 C7 C8 C9 -56.33(15) . . . . ?
C6 C7 C8 Fe1 57.59(14) . . . . ?
C11 C7 C8 Fe1 -121.5(2) . . . . ?
C7 C8 C9 C10 -0.8(2) . . . . ?
Fe1 C8 C9 C10 -58.52(13) . . . . ?
C7 C8 C9 S2 178.73(15) . . . . ?
Fe1 C8 C9 S2 120.97(16) . . . . ?
C7 C8 C9 Fe1 57.76(15) . . . . ?
C7 C6 C10 C9 0.8(2) . . . . ?
Cl1 C6 C10 C9 -173.38(16) . . . . ?
Fe1 C6 C10 C9 60.16(14) . . . . ?
C7 C6 C10 S1 -175.16(15) . . . . ?
Cl1 C6 C10 S1 10.7(3) . . . . ?
Fe1 C6 C10 S1 -115.79(16) . . . . ?
C7 C6 C10 Fe1 -59.37(15) . . . . ?
Cl1 C6 C10 Fe1 126.47(17) . . . . ?
C8 C9 C10 C6 0.0(2) . . . . ?
S2 C9 C10 C6 -179.46(16) . . . . ?
Fe1 C9 C10 C6 -60.72(14) . . . . ?
C8 C9 C10 S1 175.86(15) . . . . ?
S2 C9 C10 S1 -3.6(3) . . . . ?
Fe1 C9 C10 S1 115.16(17) . . . . ?
C8 C9 C10 Fe1 60.70(14) . . . . ?
S2 C9 C10 Fe1 -118.74(18) . . . . ?
C8 C7 C11 N12 -74.4(3) . . . . ?
C6 C7 C11 N12 106.7(2) . . . . ?
Fe1 C7 C11 N12 -163.42(15) . . . . ?
C7 C11 N12 C14 -66.3(2) . . . . ?
C7 C11 N12 C13 171.38(19) . . . . ?
C6 C10 S1 O17 156.36(18) . . . . ?
C9 C10 S1 O17 -18.8(2) . . . . ?
Fe1 C10 S1 O17 68.50(16) . . . . ?
C6 C10 S1 O16 17.6(2) . . . . ?
C9 C10 S1 O16 -157.60(18) . . . . ?
Fe1 C10 S1 O16 -70.30(16) . . . . ?
C6 C10 S1 F15 -92.62(19) . . . . ?
C9 C10 S1 F15 92.21(19) . . . . ?
Fe1 C10 S1 F15 179.51(12) . . . . ?
C8 C9 S2 C18 82.23(19) . . . . ?
C10 C9 S2 C18 -98.4(2) . . . . ?
Fe1 C9 S2 C18 171.99(13) . . . . ?
C9 S2 C18 C19 -149.96(17) . . . . ?
C9 S2 C18 C23 32.9(2) . . . . ?
C23 C18 C19 C20 1.5(3) . . . . ?
S2 C18 C19 C20 -175.70(17) . . . . ?
C18 C19 C20 C21 -1.2(4) . . . . ?
C19 C20 C21 C22 0.1(4) . . . . ?
C20 C21 C22 C23 0.7(3) . . . . ?
C21 C22 C23 C18 -0.5(3) . . . . ?
C19 C18 C23 C22 -0.7(3) . . . . ?
S2 C18 C23 C22 176.37(16) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


####################################################################### 
# 
# 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_WE10031
_database_code_depnum_ccdc_archive 'CCDC 2189770'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;ISCR
France
;
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2022-09-25 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 12 mars 2020                                             #
#------------------------------------------------------------------------------#


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H10 F6 Fe O3 S'
_chemical_formula_sum            'C13 H10 F6 Fe O3 S'
_chemical_formula_weight         416.12
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                            UNIT CELL INFORMATION                             #
#------------------------------------------------------------------------------#


_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.8905(8)
_cell_length_b                   7.3007(7)
_cell_length_c                   22.9465(19)
_cell_angle_alpha                90
_cell_angle_beta                 93.063(3)
_cell_angle_gamma                90
_cell_volume                     1487.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    9899
_cell_measurement_theta_min      2.7900
_cell_measurement_theta_max      27.5027
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      -0.0933167
_diffrn_orient_matrix_UB_21      -0.0428656
_diffrn_orient_matrix_UB_31      0.0462867
_diffrn_orient_matrix_UB_12      0.0583753
_diffrn_orient_matrix_UB_22      -0.1238760
_diffrn_orient_matrix_UB_32      0.0029679
_diffrn_orient_matrix_UB_13      0.0139043
_diffrn_orient_matrix_UB_23      0.0075268
_diffrn_orient_matrix_UB_33      0.0406772


#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.080
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.858
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             832
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.704
_exptl_absorpt_correction_T_max  0.906

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.0
_diffrn_source_voltage           50.0
_diffrn_reflns_av_r_equivalents  0.0323
_diffrn_reflns_av_uneti/neti     0.0271
_diffrn_reflns_number            15940
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.294
_diffrn_reflns_theta_max         27.530
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_reflns_number_total             3413
_reflns_number_gt                3096
_reflns_threshold_expression     >2sigma(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.
;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (G. Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2016)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2019)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0263P)²+1.8087P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         3413
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0285
_refine_ls_wR_factor_ref         0.0696
_refine_ls_wR_factor_gt          0.0665
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.073

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.21583(3) 0.59787(3) 0.68202(2) 0.01360(8) Uani 1 1 d . . . . .
S1 S 0.53930(5) 0.52418(6) 0.61964(2) 0.01552(10) Uani 1 1 d . . . . .
C1 C 0.2070(2) 0.3972(3) 0.74372(9) 0.0290(4) Uani 1 1 d . . . . .
H1 H 0.280666 0.373856 0.774339 0.035 Uiso 1 1 calc R U . . .
C2 C 0.0815(2) 0.5161(3) 0.74671(8) 0.0226(4) Uani 1 1 d . . . . .
H2 H 0.056571 0.586607 0.779626 0.027 Uiso 1 1 calc R U . . .
C3 C -0.0002(2) 0.5112(3) 0.69189(9) 0.0241(4) Uani 1 1 d . . . . .
H3 H -0.089614 0.577765 0.681728 0.029 Uiso 1 1 calc R U . . .
C4 C 0.0748(3) 0.3895(3) 0.65486(9) 0.0307(5) Uani 1 1 d . . . . .
H4 H 0.044617 0.360365 0.615622 0.037 Uiso 1 1 calc R U . . .
C5 C 0.2033(3) 0.3192(3) 0.68701(10) 0.0336(5) Uani 1 1 d . . . . .
H5 H 0.274254 0.234766 0.672989 0.040 Uiso 1 1 calc R U . . .
C6 C 0.27758(19) 0.7394(2) 0.61055(7) 0.0163(3) Uani 1 1 d . . . . .
H6 H 0.250564 0.711452 0.570935 0.020 Uiso 1 1 calc R U . . .
C7 C 0.1996(2) 0.8579(2) 0.64748(8) 0.0194(4) Uani 1 1 d . . . . .
H7 H 0.110240 0.923880 0.636720 0.023 Uiso 1 1 calc R U . . .
C8 C 0.2775(2) 0.8618(3) 0.70352(8) 0.0205(4) Uani 1 1 d . . . . .
H8 H 0.248643 0.930959 0.736162 0.025 Uiso 1 1 calc R U . . .
C9 C 0.4048(2) 0.7456(3) 0.70248(7) 0.0189(4) Uani 1 1 d . . . . .
H9 H 0.476185 0.722102 0.733891 0.023 Uiso 1 1 calc R U . . .
C10 C 0.40509(18) 0.6700(2) 0.64452(7) 0.0149(3) Uani 1 1 d . . . . .
O11 O 0.48746(15) 0.44558(19) 0.56538(5) 0.0208(3) Uani 1 1 d . . . . .
O12 O 0.60481(16) 0.4154(2) 0.66564(6) 0.0260(3) Uani 1 1 d . . . . .
O13 O 0.67684(13) 0.66400(19) 0.60655(5) 0.0175(3) Uani 1 1 d . . . . .
C14 C 0.6738(2) 0.7614(3) 0.55277(7) 0.0191(4) Uani 1 1 d . . . . .
H14 H 0.580761 0.728017 0.528705 0.023 Uiso 1 1 calc R U . . .
C15 C 0.8125(2) 0.7022(3) 0.52113(8) 0.0300(5) Uani 1 1 d . . . . .
F16 F 0.81235(15) 0.5223(2) 0.51345(6) 0.0412(3) Uani 1 1 d . . . . .
F17 F 0.94045(14) 0.7450(2) 0.55065(6) 0.0486(4) Uani 1 1 d . . . . .
F18 F 0.81354(18) 0.7812(3) 0.46887(6) 0.0521(4) Uani 1 1 d . . . . .
C19 C 0.6714(2) 0.9658(3) 0.56683(9) 0.0290(4) Uani 1 1 d . . . . .
F20 F 0.54701(17) 1.00874(19) 0.59291(7) 0.0440(4) Uani 1 1 d . . . . .
F21 F 0.6743(2) 1.0665(2) 0.51862(7) 0.0516(4) Uani 1 1 d . . . . .
F22 F 0.78775(18) 1.0160(2) 0.60211(7) 0.0479(4) Uani 1 1 d . . . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_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 C10 2.0007(17) . ?
Fe1 C9 2.0304(18) . ?
Fe1 C6 2.0383(17) . ?
Fe1 C5 2.041(2) . ?
Fe1 C1 2.042(2) . ?
Fe1 C2 2.0435(18) . ?
Fe1 C4 2.047(2) . ?
Fe1 C3 2.0463(18) . ?
Fe1 C8 2.0560(19) . ?
Fe1 C7 2.0595(18) . ?
S1 O12 1.4208(14) . ?
S1 O11 1.4250(13) . ?
S1 O13 1.6329(13) . ?
S1 C10 1.7193(18) . ?
C1 C5 1.419(3) . ?
C1 C2 1.418(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.419(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.420(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.422(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.418(2) . ?
C6 C10 1.434(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.428(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.416(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.440(2) . ?
C9 H9 0.9500 . ?
O13 C14 1.423(2) . ?
C14 C19 1.528(3) . ?
C14 C15 1.527(3) . ?
C14 H14 1.0000 . ?
C15 F16 1.326(3) . ?
C15 F17 1.329(2) . ?
C15 F18 1.331(3) . ?
C19 F20 1.323(3) . ?
C19 F22 1.330(3) . ?
C19 F21 1.330(2) . ?

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 Fe1 C9 41.85(7) . . ?
C10 Fe1 C6 41.57(7) . . ?
C9 Fe1 C6 70.22(7) . . ?
C10 Fe1 C5 109.63(8) . . ?
C9 Fe1 C5 124.29(9) . . ?
C6 Fe1 C5 124.64(8) . . ?
C10 Fe1 C1 123.46(8) . . ?
C9 Fe1 C1 106.42(8) . . ?
C6 Fe1 C1 160.68(8) . . ?
C5 Fe1 C1 40.68(9) . . ?
C10 Fe1 C2 157.93(7) . . ?
C9 Fe1 C2 119.71(8) . . ?
C6 Fe1 C2 157.76(8) . . ?
C5 Fe1 C2 68.42(8) . . ?
C1 Fe1 C2 40.62(8) . . ?
C10 Fe1 C4 125.46(8) . . ?
C9 Fe1 C4 161.97(9) . . ?
C6 Fe1 C4 108.59(8) . . ?
C5 Fe1 C4 40.72(10) . . ?
C1 Fe1 C4 68.43(9) . . ?
C2 Fe1 C4 68.40(8) . . ?
C10 Fe1 C3 160.89(7) . . ?
C9 Fe1 C3 155.32(8) . . ?
C6 Fe1 C3 122.72(7) . . ?
C5 Fe1 C3 68.37(9) . . ?
C1 Fe1 C3 68.30(8) . . ?
C2 Fe1 C3 40.61(8) . . ?
C4 Fe1 C3 40.60(8) . . ?
C10 Fe1 C8 68.72(7) . . ?
C9 Fe1 C8 40.53(7) . . ?
C6 Fe1 C8 68.79(7) . . ?
C5 Fe1 C8 159.26(9) . . ?
C1 Fe1 C8 121.70(9) . . ?
C2 Fe1 C8 104.96(8) . . ?
C4 Fe1 C8 157.01(9) . . ?
C3 Fe1 C8 120.20(8) . . ?
C10 Fe1 C7 68.61(7) . . ?
C9 Fe1 C7 68.87(8) . . ?
C6 Fe1 C7 40.48(7) . . ?
C5 Fe1 C7 159.65(9) . . ?
C1 Fe1 C7 157.48(8) . . ?
C2 Fe1 C7 121.14(8) . . ?
C4 Fe1 C7 122.59(9) . . ?
C3 Fe1 C7 106.30(8) . . ?
C8 Fe1 C7 40.61(7) . . ?
O12 S1 O11 121.64(9) . . ?
O12 S1 O13 101.83(8) . . ?
O11 S1 O13 107.55(7) . . ?
O12 S1 C10 111.32(8) . . ?
O11 S1 C10 109.98(8) . . ?
O13 S1 C10 102.35(8) . . ?
C5 C1 C2 108.09(19) . . ?
C5 C1 Fe1 69.64(12) . . ?
C2 C1 Fe1 69.75(11) . . ?
C5 C1 H1 126.0 . . ?
C2 C1 H1 126.0 . . ?
Fe1 C1 H1 126.2 . . ?
C1 C2 C3 107.97(18) . . ?
C1 C2 Fe1 69.63(11) . . ?
C3 C2 Fe1 69.80(10) . . ?
C1 C2 H2 126.0 . . ?
C3 C2 H2 126.0 . . ?
Fe1 C2 H2 126.1 . . ?
C4 C3 C2 108.14(18) . . ?
C4 C3 Fe1 69.72(11) . . ?
C2 C3 Fe1 69.59(10) . . ?
C4 C3 H3 125.9 . . ?
C2 C3 H3 125.9 . . ?
Fe1 C3 H3 126.3 . . ?
C3 C4 C5 107.80(19) . . ?
C3 C4 Fe1 69.68(11) . . ?
C5 C4 Fe1 69.43(12) . . ?
C3 C4 H4 126.1 . . ?
C5 C4 H4 126.1 . . ?
Fe1 C4 H4 126.4 . . ?
C1 C5 C4 108.00(18) . . ?
C1 C5 Fe1 69.68(12) . . ?
C4 C5 Fe1 69.85(12) . . ?
C1 C5 H5 126.0 . . ?
C4 C5 H5 126.0 . . ?
Fe1 C5 H5 126.0 . . ?
C7 C6 C10 106.78(15) . . ?
C7 C6 Fe1 70.56(10) . . ?
C10 C6 Fe1 67.81(9) . . ?
C7 C6 H6 126.6 . . ?
C10 C6 H6 126.6 . . ?
Fe1 C6 H6 126.6 . . ?
C6 C7 C8 108.71(16) . . ?
C6 C7 Fe1 68.96(10) . . ?
C8 C7 Fe1 69.56(11) . . ?
C6 C7 H7 125.6 . . ?
C8 C7 H7 125.6 . . ?
Fe1 C7 H7 127.4 . . ?
C9 C8 C7 108.84(16) . . ?
C9 C8 Fe1 68.76(10) . . ?
C7 C8 Fe1 69.83(10) . . ?
C9 C8 H8 125.6 . . ?
C7 C8 H8 125.6 . . ?
Fe1 C8 H8 127.4 . . ?
C8 C9 C10 106.62(15) . . ?
C8 C9 Fe1 70.71(10) . . ?
C10 C9 Fe1 67.97(9) . . ?
C8 C9 H9 126.7 . . ?
C10 C9 H9 126.7 . . ?
Fe1 C9 H9 126.2 . . ?
C6 C10 C9 109.05(15) . . ?
C6 C10 S1 125.52(13) . . ?
C9 C10 S1 125.41(13) . . ?
C6 C10 Fe1 70.62(10) . . ?
C9 C10 Fe1 70.18(10) . . ?
S1 C10 Fe1 126.47(10) . . ?
C14 O13 S1 119.48(11) . . ?
O13 C14 C19 107.74(15) . . ?
O13 C14 C15 107.04(16) . . ?
C19 C14 C15 113.42(17) . . ?
O13 C14 H14 109.5 . . ?
C19 C14 H14 109.5 . . ?
C15 C14 H14 109.5 . . ?
F16 C15 F17 107.20(19) . . ?
F16 C15 F18 108.04(17) . . ?
F17 C15 F18 108.10(18) . . ?
F16 C15 C14 110.37(17) . . ?
F17 C15 C14 112.45(16) . . ?
F18 C15 C14 110.52(18) . . ?
F20 C19 F22 107.53(19) . . ?
F20 C19 F21 107.42(19) . . ?
F22 C19 F21 107.75(18) . . ?
F20 C19 C14 110.39(16) . . ?
F22 C19 C14 112.24(18) . . ?
F21 C19 C14 111.31(18) . . ?

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
C5 C1 C2 C3 0.2(2) . . . . ?
Fe1 C1 C2 C3 59.50(13) . . . . ?
C5 C1 C2 Fe1 -59.29(14) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
Fe1 C2 C3 C4 59.26(13) . . . . ?
C1 C2 C3 Fe1 -59.39(14) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
Fe1 C3 C4 C5 59.18(14) . . . . ?
C2 C3 C4 Fe1 -59.18(13) . . . . ?
C2 C1 C5 C4 -0.2(2) . . . . ?
Fe1 C1 C5 C4 -59.56(14) . . . . ?
C2 C1 C5 Fe1 59.36(14) . . . . ?
C3 C4 C5 C1 0.1(2) . . . . ?
Fe1 C4 C5 C1 59.46(14) . . . . ?
C3 C4 C5 Fe1 -59.34(14) . . . . ?
C10 C6 C7 C8 0.0(2) . . . . ?
Fe1 C6 C7 C8 58.31(13) . . . . ?
C10 C6 C7 Fe1 -58.35(12) . . . . ?
C6 C7 C8 C9 -0.2(2) . . . . ?
Fe1 C7 C8 C9 57.78(13) . . . . ?
C6 C7 C8 Fe1 -57.94(13) . . . . ?
C7 C8 C9 C10 0.3(2) . . . . ?
Fe1 C8 C9 C10 58.72(12) . . . . ?
C7 C8 C9 Fe1 -58.43(13) . . . . ?
C7 C6 C10 C9 0.2(2) . . . . ?
Fe1 C6 C10 C9 -59.88(12) . . . . ?
C7 C6 C10 S1 -178.35(13) . . . . ?
Fe1 C6 C10 S1 121.54(14) . . . . ?
C7 C6 C10 Fe1 60.11(12) . . . . ?
C8 C9 C10 C6 -0.3(2) . . . . ?
Fe1 C9 C10 C6 60.16(12) . . . . ?
C8 C9 C10 S1 178.25(13) . . . . ?
Fe1 C9 C10 S1 -121.27(14) . . . . ?
C8 C9 C10 Fe1 -60.48(12) . . . . ?
O12 S1 C10 C6 -152.29(15) . . . . ?
O11 S1 C10 C6 -14.46(18) . . . . ?
O13 S1 C10 C6 99.61(16) . . . . ?
O12 S1 C10 C9 29.37(18) . . . . ?
O11 S1 C10 C9 167.19(15) . . . . ?
O13 S1 C10 C9 -78.73(16) . . . . ?
O12 S1 C10 Fe1 -61.10(13) . . . . ?
O11 S1 C10 Fe1 76.72(12) . . . . ?
O13 S1 C10 Fe1 -169.20(10) . . . . ?
O12 S1 O13 C14 162.05(13) . . . . ?
O11 S1 O13 C14 33.13(15) . . . . ?
C10 S1 O13 C14 -82.73(14) . . . . ?
S1 O13 C14 C19 119.08(14) . . . . ?
S1 O13 C14 C15 -118.60(14) . . . . ?
O13 C14 C15 F16 57.5(2) . . . . ?
C19 C14 C15 F16 176.16(16) . . . . ?
O13 C14 C15 F17 -62.2(2) . . . . ?
C19 C14 C15 F17 56.5(2) . . . . ?
O13 C14 C15 F18 176.92(16) . . . . ?
C19 C14 C15 F18 -64.4(2) . . . . ?
O13 C14 C19 F20 -63.2(2) . . . . ?
C15 C14 C19 F20 178.52(17) . . . . ?
O13 C14 C19 F22 56.7(2) . . . . ?
C15 C14 C19 F22 -61.5(2) . . . . ?
O13 C14 C19 F21 177.61(16) . . . . ?
C15 C14 C19 F21 59.3(2) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


####################################################################### 
# 
# 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_WE17901
_database_code_depnum_ccdc_archive 'CCDC 2189758'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;ISCR
France
;
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2022-09-25 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 11 janvier 2022                                          #
#------------------------------------------------------------------------------#


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H15 Cl F2 Fe O2 S Si'
_chemical_formula_sum            'C13 H15 Cl F2 Fe O2 S Si'
_chemical_formula_weight         392.70
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
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                   7.1087(16)
_cell_length_b                   13.056(3)
_cell_length_c                   17.190(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.972(9)
_cell_angle_gamma                90
_cell_volume                     1594.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9918
_cell_measurement_theta_min      2.8385
_cell_measurement_theta_max      27.4693
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      -0.0371555
_diffrn_orient_matrix_UB_21      -0.0801252
_diffrn_orient_matrix_UB_31      -0.1095967
_diffrn_orient_matrix_UB_12      -0.0705018
_diffrn_orient_matrix_UB_22      -0.0070829
_diffrn_orient_matrix_UB_32      0.0290798
_diffrn_orient_matrix_UB_13      -0.0172902
_diffrn_orient_matrix_UB_23      0.0463841
_diffrn_orient_matrix_UB_33      -0.0306212


#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.100
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             800
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.339
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.769
_exptl_absorpt_correction_T_max  0.875

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

# Software                   : BIS V6.2.15/2021-03-15 && APEX4 2021.10-0       #
# Number of scans            :        4                                        #
# Total number of frames [*] :      656                                        #
# Total length of scans  [*] :   328.00 (deg.)                                 #
# Rotation speed         [*] :     6.00 sec./deg.                              #
# Total exposition time  [*] :         32.8 min.                               #
#                                                                              #
#  [*] fast scan not included                                                  #
#                                                                              #
#    Scan  Time(s) Width DX(mm) Frames Range 2Theta  Omega    Phi    Chi  T(K) #
#..............................................................................#
#                                                                              #
#  1 Fast     1.0  1.00    34.0   180  180.0    0.0    0.0    0.0   54.7 150.0 #
#  2 Fast@    1.0  1.00    34.0   180  180.0    0.0    0.0  180.0   54.7 150.0 #
#  3 Phi      3.0  0.50    34.0   462  231.0    0.1    1.9  256.5  -24.0 150.0 #
#  4 Omega    3.0  0.50    34.0   194   97.0    0.1    2.5   72.0  -44.5 150.0 #
#                                                                              #
#  @: attenuated beam                                                          #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.00
_diffrn_source_voltage           50.00
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0221
_diffrn_reflns_av_r_equivalents  0.0307
_diffrn_reflns_number            20463
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.065
_diffrn_reflns_theta_max         27.472
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_reflns_number_total             3631
_reflns_number_gt                3440
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2021)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0238P)²+0.9454P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         3631
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0252
_refine_ls_wR_factor_ref         0.0620
_refine_ls_wR_factor_gt          0.0612
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.065

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 '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'
Cl Cl 0.1484 0.1585 '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'

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 0.67329(3) 0.35565(2) 0.35256(2) 0.01650(7) Uani 1 1 d . . . . .
C1 C 0.9540(2) 0.33739(14) 0.33189(11) 0.0305(4) Uani 1 1 d . . . . .
H1 H 1.005502 0.310579 0.285850 0.037 Uiso 1 1 calc R U . . .
C2 C 0.9052(3) 0.28016(15) 0.39759(12) 0.0363(4) Uani 1 1 d . . . . .
H2 H 0.917089 0.208101 0.403654 0.044 Uiso 1 1 calc R U . . .
C3 C 0.8347(3) 0.34982(17) 0.45335(11) 0.0397(5) Uani 1 1 d . . . . .
H3 H 0.791412 0.332398 0.503324 0.048 Uiso 1 1 calc R U . . .
C4 C 0.8403(2) 0.44925(15) 0.42130(11) 0.0336(4) Uani 1 1 d . . . . .
H4 H 0.801824 0.510551 0.445904 0.040 Uiso 1 1 calc R U . . .
C5 C 0.9135(2) 0.44145(13) 0.34611(10) 0.0290(4) Uani 1 1 d . . . . .
H5 H 0.932152 0.496642 0.311201 0.035 Uiso 1 1 calc R U . . .
C6 C 0.3998(2) 0.37215(12) 0.37652(8) 0.0208(3) Uani 1 1 d . . . . .
C7 C 0.4388(2) 0.26774(12) 0.36643(8) 0.0212(3) Uani 1 1 d . . . . .
C8 C 0.5076(2) 0.25404(11) 0.29036(8) 0.0195(3) Uani 1 1 d . . . . .
H8 H 0.544731 0.190324 0.269055 0.023 Uiso 1 1 calc R U . . .
C9 C 0.5127(2) 0.35058(11) 0.25054(8) 0.0177(3) Uani 1 1 d . . . . .
C10 C 0.4435(2) 0.42435(11) 0.30605(8) 0.0184(3) Uani 1 1 d . . . . .
F11 F 0.32531(14) 0.41299(8) 0.43952(5) 0.0297(2) Uani 1 1 d . . . . .
Cl1 Cl 0.40520(7) 0.17417(3) 0.43464(2) 0.03370(11) Uani 1 1 d . . . . .
S1 S 0.41682(6) 0.55377(3) 0.29125(2) 0.02597(10) Uani 1 1 d . . . . .
C12 C 0.6343(3) 0.22842(13) 0.11564(9) 0.0285(3) Uani 1 1 d . . . . .
H12A H 0.738181 0.200923 0.148241 0.043 Uiso 1 1 calc R U . . .
H12B H 0.669497 0.228006 0.061021 0.043 Uiso 1 1 calc R U . . .
H12C H 0.521989 0.185966 0.121617 0.043 Uiso 1 1 calc R U . . .
C13 C 0.3786(3) 0.41294(16) 0.08741(10) 0.0399(4) Uani 1 1 d . . . . .
H13A H 0.407706 0.412222 0.032104 0.060 Uiso 1 1 calc R U . . .
H13B H 0.352659 0.483347 0.103646 0.060 Uiso 1 1 calc R U . . .
H13C H 0.267762 0.370161 0.095695 0.060 Uiso 1 1 calc R U . . .
C14 C 0.7955(3) 0.44278(15) 0.13285(11) 0.0382(4) Uani 1 1 d . . . . .
H14A H 0.904019 0.411679 0.160448 0.057 Uiso 1 1 calc R U . . .
H14B H 0.773351 0.511328 0.153881 0.057 Uiso 1 1 calc R U . . .
H14C H 0.820631 0.447973 0.077291 0.057 Uiso 1 1 calc R U . . .
Si1 Si 0.58329(6) 0.36172(3) 0.14599(2) 0.02089(10) Uani 1 1 d . . . . .
F15 F 0.22394(15) 0.55415(9) 0.24336(7) 0.0407(3) Uani 1 1 d . . . . .
O16 O 0.3814(2) 0.60563(10) 0.36126(8) 0.0458(4) Uani 1 1 d . . . . .
O17 O 0.54819(19) 0.59160(9) 0.23854(8) 0.0361(3) Uani 1 1 d . . . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_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 C10 2.0057(15) . ?
Fe1 C6 2.0125(16) . ?
Fe1 C7 2.0448(16) . ?
Fe1 C3 2.0462(18) . ?
Fe1 C5 2.0484(17) . ?
Fe1 C2 2.0495(17) . ?
Fe1 C8 2.0503(15) . ?
Fe1 C4 2.0502(17) . ?
Fe1 C1 2.0531(17) . ?
Fe1 C9 2.0603(15) . ?
C1 C2 1.408(3) . ?
C1 C5 1.412(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.425(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.411(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.413(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 F11 1.3331(17) . ?
C6 C7 1.403(2) . ?
C6 C10 1.433(2) . ?
C7 C8 1.423(2) . ?
C7 Cl1 1.7157(15) . ?
C8 C9 1.435(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.454(2) . ?
C9 Si1 1.8882(15) . ?
C10 S1 1.7182(16) . ?
S1 O16 1.4111(14) . ?
S1 O17 1.4126(13) . ?
S1 F15 1.5748(12) . ?
C12 Si1 1.8562(17) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 Si1 1.8650(19) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 Si1 1.8626(19) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
C10 Fe1 C6 41.79(6) . . ?
C10 Fe1 C7 68.98(6) . . ?
C6 Fe1 C7 40.45(6) . . ?
C10 Fe1 C3 141.20(7) . . ?
C6 Fe1 C3 110.37(7) . . ?
C7 Fe1 C3 108.42(7) . . ?
C10 Fe1 C5 113.76(7) . . ?
C6 Fe1 C5 139.95(7) . . ?
C7 Fe1 C5 176.21(6) . . ?
C3 Fe1 C5 67.79(8) . . ?
C10 Fe1 C2 177.66(7) . . ?
C6 Fe1 C2 138.10(7) . . ?
C7 Fe1 C2 109.54(7) . . ?
C3 Fe1 C2 40.72(8) . . ?
C5 Fe1 C2 67.80(8) . . ?
C10 Fe1 C8 68.66(6) . . ?
C6 Fe1 C8 68.55(6) . . ?
C7 Fe1 C8 40.67(6) . . ?
C3 Fe1 C8 135.46(8) . . ?
C5 Fe1 C8 142.24(7) . . ?
C2 Fe1 C8 109.02(7) . . ?
C10 Fe1 C4 114.26(7) . . ?
C6 Fe1 C4 111.26(7) . . ?
C7 Fe1 C4 136.53(7) . . ?
C3 Fe1 C4 40.30(8) . . ?
C5 Fe1 C4 40.34(7) . . ?
C2 Fe1 C4 68.07(8) . . ?
C8 Fe1 C4 175.70(7) . . ?
C10 Fe1 C1 140.02(7) . . ?
C6 Fe1 C1 178.09(7) . . ?
C7 Fe1 C1 139.14(7) . . ?
C3 Fe1 C1 67.80(8) . . ?
C5 Fe1 C1 40.27(7) . . ?
C2 Fe1 C1 40.13(8) . . ?
C8 Fe1 C1 112.27(7) . . ?
C4 Fe1 C1 67.77(7) . . ?
C10 Fe1 C9 41.86(6) . . ?
C6 Fe1 C9 70.54(6) . . ?
C7 Fe1 C9 69.58(6) . . ?
C3 Fe1 C9 176.00(8) . . ?
C5 Fe1 C9 114.20(7) . . ?
C2 Fe1 C9 136.13(7) . . ?
C8 Fe1 C9 40.88(6) . . ?
C4 Fe1 C9 143.39(7) . . ?
C1 Fe1 C9 111.25(7) . . ?
C2 C1 C5 108.32(16) . . ?
C2 C1 Fe1 69.80(10) . . ?
C5 C1 Fe1 69.68(9) . . ?
C2 C1 H1 125.8 . . ?
C5 C1 H1 125.8 . . ?
Fe1 C1 H1 126.3 . . ?
C1 C2 C3 107.65(17) . . ?
C1 C2 Fe1 70.07(10) . . ?
C3 C2 Fe1 69.52(10) . . ?
C1 C2 H2 126.2 . . ?
C3 C2 H2 126.2 . . ?
Fe1 C2 H2 125.8 . . ?
C4 C3 C2 108.00(16) . . ?
C4 C3 Fe1 70.00(10) . . ?
C2 C3 Fe1 69.76(10) . . ?
C4 C3 H3 126.0 . . ?
C2 C3 H3 126.0 . . ?
Fe1 C3 H3 125.8 . . ?
C3 C4 C5 107.88(16) . . ?
C3 C4 Fe1 69.69(10) . . ?
C5 C4 Fe1 69.76(9) . . ?
C3 C4 H4 126.1 . . ?
C5 C4 H4 126.1 . . ?
Fe1 C4 H4 126.1 . . ?
C1 C5 C4 108.14(16) . . ?
C1 C5 Fe1 70.04(10) . . ?
C4 C5 Fe1 69.90(10) . . ?
C1 C5 H5 125.9 . . ?
C4 C5 H5 125.9 . . ?
Fe1 C5 H5 125.7 . . ?
F11 C6 C7 125.08(14) . . ?
F11 C6 C10 126.87(14) . . ?
C7 C6 C10 107.95(13) . . ?
F11 C6 Fe1 128.51(11) . . ?
C7 C6 Fe1 71.01(9) . . ?
C10 C6 Fe1 68.85(8) . . ?
C6 C7 C8 108.14(13) . . ?
C6 C7 Cl1 125.08(12) . . ?
C8 C7 Cl1 126.78(12) . . ?
C6 C7 Fe1 68.54(9) . . ?
C8 C7 Fe1 69.87(8) . . ?
Cl1 C7 Fe1 127.77(9) . . ?
C7 C8 C9 110.06(13) . . ?
C7 C8 Fe1 69.46(8) . . ?
C9 C8 Fe1 69.94(8) . . ?
C7 C8 H8 125.0 . . ?
C9 C8 H8 125.0 . . ?
Fe1 C8 H8 127.3 . . ?
C8 C9 C10 104.72(12) . . ?
C8 C9 Si1 122.24(11) . . ?
C10 C9 Si1 132.91(11) . . ?
C8 C9 Fe1 69.19(8) . . ?
C10 C9 Fe1 67.06(8) . . ?
Si1 C9 Fe1 130.55(8) . . ?
C6 C10 C9 109.14(13) . . ?
C6 C10 S1 124.53(11) . . ?
C9 C10 S1 126.34(11) . . ?
C6 C10 Fe1 69.36(8) . . ?
C9 C10 Fe1 71.08(8) . . ?
S1 C10 Fe1 125.66(8) . . ?
O16 S1 O17 121.37(9) . . ?
O16 S1 F15 105.46(8) . . ?
O17 S1 F15 104.27(8) . . ?
O16 S1 C10 111.57(8) . . ?
O17 S1 C10 111.52(7) . . ?
F15 S1 C10 99.79(7) . . ?
Si1 C12 H12A 109.5 . . ?
Si1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
Si1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
Si1 C13 H13A 109.5 . . ?
Si1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
Si1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
Si1 C14 H14A 109.5 . . ?
Si1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
Si1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 Si1 C14 109.39(9) . . ?
C12 Si1 C13 109.91(9) . . ?
C14 Si1 C13 110.54(10) . . ?
C12 Si1 C9 104.84(7) . . ?
C14 Si1 C9 113.71(7) . . ?
C13 Si1 C9 108.28(8) . . ?

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
C5 C1 C2 C3 -0.37(19) . . . . ?
Fe1 C1 C2 C3 -59.61(12) . . . . ?
C5 C1 C2 Fe1 59.23(12) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
Fe1 C2 C3 C4 -59.80(12) . . . . ?
C1 C2 C3 Fe1 59.96(12) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
Fe1 C3 C4 C5 -59.53(12) . . . . ?
C2 C3 C4 Fe1 59.65(12) . . . . ?
C2 C1 C5 C4 0.45(19) . . . . ?
Fe1 C1 C5 C4 59.75(11) . . . . ?
C2 C1 C5 Fe1 -59.30(12) . . . . ?
C3 C4 C5 C1 -0.35(19) . . . . ?
Fe1 C4 C5 C1 -59.84(11) . . . . ?
C3 C4 C5 Fe1 59.49(12) . . . . ?
F11 C6 C7 C8 176.92(14) . . . . ?
C10 C6 C7 C8 0.35(17) . . . . ?
Fe1 C6 C7 C8 -58.81(11) . . . . ?
F11 C6 C7 Cl1 -2.4(2) . . . . ?
C10 C6 C7 Cl1 -178.96(11) . . . . ?
Fe1 C6 C7 Cl1 121.88(13) . . . . ?
F11 C6 C7 Fe1 -124.26(15) . . . . ?
C10 C6 C7 Fe1 59.16(10) . . . . ?
C6 C7 C8 C9 -0.22(17) . . . . ?
Cl1 C7 C8 C9 179.07(12) . . . . ?
Fe1 C7 C8 C9 -58.21(10) . . . . ?
C6 C7 C8 Fe1 57.99(11) . . . . ?
Cl1 C7 C8 Fe1 -122.72(13) . . . . ?
C7 C8 C9 C10 0.00(16) . . . . ?
Fe1 C8 C9 C10 -57.92(9) . . . . ?
C7 C8 C9 Si1 -176.45(11) . . . . ?
Fe1 C8 C9 Si1 125.63(11) . . . . ?
C7 C8 C9 Fe1 57.92(11) . . . . ?
F11 C6 C10 C9 -176.85(14) . . . . ?
C7 C6 C10 C9 -0.36(17) . . . . ?
Fe1 C6 C10 C9 60.17(10) . . . . ?
F11 C6 C10 S1 3.2(2) . . . . ?
C7 C6 C10 S1 179.68(11) . . . . ?
Fe1 C6 C10 S1 -119.80(12) . . . . ?
F11 C6 C10 Fe1 122.98(15) . . . . ?
C7 C6 C10 Fe1 -60.52(11) . . . . ?
C8 C9 C10 C6 0.22(16) . . . . ?
Si1 C9 C10 C6 176.11(12) . . . . ?
Fe1 C9 C10 C6 -59.11(10) . . . . ?
C8 C9 C10 S1 -179.82(11) . . . . ?
Si1 C9 C10 S1 -3.9(2) . . . . ?
Fe1 C9 C10 S1 120.85(12) . . . . ?
C8 C9 C10 Fe1 59.33(10) . . . . ?
Si1 C9 C10 Fe1 -124.78(13) . . . . ?
C6 C10 S1 O16 11.33(16) . . . . ?
C9 C10 S1 O16 -168.63(13) . . . . ?
Fe1 C10 S1 O16 -76.78(12) . . . . ?
C6 C10 S1 O17 150.59(13) . . . . ?
C9 C10 S1 O17 -29.37(16) . . . . ?
Fe1 C10 S1 O17 62.48(12) . . . . ?
C6 C10 S1 F15 -99.72(13) . . . . ?
C9 C10 S1 F15 80.32(14) . . . . ?
Fe1 C10 S1 F15 172.17(9) . . . . ?
C8 C9 Si1 C12 0.37(14) . . . . ?
C10 C9 Si1 C12 -174.93(14) . . . . ?
Fe1 C9 Si1 C12 89.61(11) . . . . ?
C8 C9 Si1 C14 -119.06(14) . . . . ?
C10 C9 Si1 C14 65.63(17) . . . . ?
Fe1 C9 Si1 C14 -29.82(13) . . . . ?
C8 C9 Si1 C13 117.67(14) . . . . ?
C10 C9 Si1 C13 -57.64(17) . . . . ?
Fe1 C9 Si1 C13 -153.09(11) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


####################################################################### 
# 
# 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_WE12841
_database_code_depnum_ccdc_archive 'CCDC 2189764'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;ISCR
France
;
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2022-09-25 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 05 fevrier 2021                                          #
#------------------------------------------------------------------------------#


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H13 F Fe O4 S'
_chemical_formula_sum            'C13 H13 F Fe O4 S'
_chemical_formula_weight         340.14
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#


_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.809(4)
_cell_length_b                   7.744(2)
_cell_length_c                   25.366(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.69(2)
_cell_angle_gamma                90
_cell_volume                     1337.0(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9903
_cell_measurement_theta_min      2.7523
_cell_measurement_theta_max      27.4632
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      0.1125497
_diffrn_orient_matrix_UB_21      -0.0943986
_diffrn_orient_matrix_UB_31      -0.0013454
_diffrn_orient_matrix_UB_12      -0.0819316
_diffrn_orient_matrix_UB_22      -0.0979676
_diffrn_orient_matrix_UB_32      0.0197975
_diffrn_orient_matrix_UB_13      -0.0032853
_diffrn_orient_matrix_UB_23      -0.0051291
_diffrn_orient_matrix_UB_33      -0.0389774


#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             696
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.708
_exptl_absorpt_correction_T_max  0.878

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

# Software                   : BIS V6.2.1/2016-03-01                           #
# Number of scans            :        3                                        #
# Total number of frames [*] :      600                                        #
# Total length of scans  [*] :   300.00 (deg.)                                 #
# Rotation speed         [*] :    30.00 sec./deg.                              #
# Total exposition time  [*] :      2 h  30.0 min.                             #
#                                                                              #
#  [*] fast scan not included                                                  #
#                                                                              #
# Measurement mode           : shutterless mode                                #
#                                                                              #
#    Scan  Time(s)  Width  DX (mm)  Frames  Theta  Omega    Phi    Chi   T(K)  #
#..............................................................................#
#                                                                              #
#  1 Phi      15.0   0.50     36.0     462   1.30 269.85 208.51  23.00 150.00  #
#  2 Omega    15.0   0.50     36.0     138   2.41 294.09 326.63  51.51 150.00  #
#  3 Fast      3.0   1.00     36.0     180   0.00 360.00   0.00  54.74 150.00  #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.00
_diffrn_source_voltage           50.00
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0439
_diffrn_reflns_av_r_equivalents  0.0553
_diffrn_reflns_number            13717
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.750
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_reflns_number_total             3047
_reflns_number_gt                2787
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (G. Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2020)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+10.4528P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         3047
_refine_ls_number_parameters     162
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0651
_refine_ls_wR_factor_ref         0.1518
_refine_ls_wR_factor_gt          0.1485
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_restrained_S_all      1.136
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.657
_refine_diff_density_min         -0.763
_refine_diff_density_rms         0.132

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'
F F 0.0171 0.0103 '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'
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'

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 0.34034(9) 0.20055(8) 0.34489(2) 0.01740(18) Uani 1 1 d . . . . .
C1A C 0.1177(10) 0.0395(7) 0.3183(3) 0.0278(15) Uani 0.544(13) 1 d G . P A 1
H1A H 0.134171 -0.075687 0.306263 0.033 Uiso 0.544(13) 1 calc R U P A 1
C2A C 0.1219(10) 0.1906(12) 0.28663(17) 0.0278(15) Uani 0.544(13) 1 d G . P A 1
H2A H 0.141619 0.194311 0.249728 0.033 Uiso 0.544(13) 1 calc R U P A 1
C3A C 0.0913(10) 0.3352(7) 0.3198(3) 0.0278(15) Uani 0.544(13) 1 d G . P A 1
H3A H 0.087045 0.452617 0.309030 0.033 Uiso 0.544(13) 1 calc R U P A 1
C4A C 0.0683(10) 0.2734(10) 0.3720(2) 0.0278(15) Uani 0.544(13) 1 d G . P A 1
H4A H 0.045868 0.342261 0.402216 0.033 Uiso 0.544(13) 1 calc R U P A 1
C5A C 0.0846(10) 0.0906(10) 0.3710(3) 0.0278(15) Uani 0.544(13) 1 d G . P A 1
H5A H 0.074994 0.015752 0.400506 0.033 Uiso 0.544(13) 1 calc R U P A 1
C1B C 0.1126(13) 0.0255(8) 0.3476(4) 0.0291(19) Uani 0.456(13) 1 d G . P A 2
H1B H 0.120209 -0.091801 0.358453 0.035 Uiso 0.456(13) 1 calc R U P A 2
C2B C 0.1336(12) 0.0875(13) 0.2954(3) 0.0291(19) Uani 0.456(13) 1 d G . P A 2
H2B H 0.157657 0.019007 0.265175 0.035 Uiso 0.456(13) 1 calc R U P A 2
C3B C 0.1123(12) 0.2699(12) 0.2962(3) 0.0291(19) Uani 0.456(13) 1 d G . P A 2
H3B H 0.119560 0.344809 0.266707 0.035 Uiso 0.456(13) 1 calc R U P A 2
C4B C 0.0781(12) 0.3206(9) 0.3490(4) 0.0291(19) Uani 0.456(13) 1 d G . P A 2
H4B H 0.058566 0.435357 0.360932 0.035 Uiso 0.456(13) 1 calc R U P A 2
C5B C 0.0783(12) 0.1695(14) 0.3807(2) 0.0291(19) Uani 0.456(13) 1 d G . P A 2
H5B H 0.058968 0.165517 0.417635 0.035 Uiso 0.456(13) 1 calc R U P A 2
C6 C 0.5965(6) 0.2651(6) 0.31064(17) 0.0195(9) Uani 1 1 d . . . . .
H6 H 0.609104 0.307608 0.275772 0.023 Uiso 1 1 calc R U . . .
C7 C 0.6068(6) 0.0894(6) 0.32668(18) 0.0218(9) Uani 1 1 d . . . . .
H7 H 0.627969 -0.006350 0.304125 0.026 Uiso 1 1 calc R U . . .
C8 C 0.5805(7) 0.0803(6) 0.38161(18) 0.0205(9) Uani 1 1 d . . . . .
H8 H 0.583038 -0.022705 0.401969 0.025 Uiso 1 1 calc R U . . .
C9 C 0.5494(6) 0.2504(5) 0.40187(16) 0.0153(8) Uani 1 1 d . . . . .
C10 C 0.5635(6) 0.3661(5) 0.35694(16) 0.0152(8) Uani 1 1 d . . . . .
S1 S 0.52655(18) 0.58441(14) 0.35554(4) 0.0222(3) Uani 1 1 d . . . . .
O11 O 0.4351(7) 0.6459(5) 0.40089(15) 0.0436(11) Uani 1 1 d . . . . .
O12 O 0.4627(7) 0.6407(5) 0.30499(15) 0.0432(11) Uani 1 1 d . . . . .
F13 F 0.7454(5) 0.6508(4) 0.36131(15) 0.0455(9) Uani 1 1 d . . . . .
C14 C 0.5201(7) 0.2958(6) 0.45826(16) 0.0193(8) Uani 1 1 d . . . . .
H14A H 0.427746 0.394129 0.460438 0.023 Uiso 1 1 calc R U . . .
H14B H 0.462586 0.196171 0.476789 0.023 Uiso 1 1 calc R U . . .
O15 O 0.7087(5) 0.3421(4) 0.48351(12) 0.0192(6) Uani 1 1 d . . . . .
C16 C 0.8082(7) 0.2124(6) 0.50727(17) 0.0228(9) Uani 1 1 d . . . . .
O17 O 0.7535(5) 0.0643(4) 0.50733(15) 0.0306(8) Uani 1 1 d . . . . .
C18 C 0.9934(8) 0.2757(7) 0.5341(2) 0.0309(11) Uani 1 1 d . . . . .
H18A H 1.076560 0.176926 0.543994 0.046 Uiso 1 1 calc R U . . .
H18B H 0.960778 0.340553 0.565874 0.046 Uiso 1 1 calc R U . . .
H18C H 1.063931 0.351046 0.510086 0.046 Uiso 1 1 calc R U . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_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 C10 2.005(4) . ?
Fe1 C4B 2.018(8) . ?
Fe1 C3B 2.027(8) . ?
Fe1 C6 2.034(5) . ?
Fe1 C9 2.035(4) . ?
Fe1 C5B 2.040(8) . ?
Fe1 C2B 2.055(7) . ?
Fe1 C1A 2.062(6) . ?
Fe1 C1B 2.062(8) . ?
Fe1 C5A 2.065(6) . ?
Fe1 C2A 2.067(6) . ?
Fe1 C7 2.073(4) . ?
C1A C2A 1.4200 . ?
C1A C5A 1.4200 . ?
C1A H1A 0.9500 . ?
C2A C3A 1.4200 . ?
C2A H2A 0.9500 . ?
C3A C4A 1.4200 . ?
C3A H3A 0.9500 . ?
C4A C5A 1.4200 . ?
C4A H4A 0.9500 . ?
C5A H5A 0.9500 . ?
C1B C2B 1.4200 . ?
C1B C5B 1.4200 . ?
C1B H1B 0.9500 . ?
C2B C3B 1.4200 . ?
C2B H2B 0.9500 . ?
C3B C4B 1.4200 . ?
C3B H3B 0.9500 . ?
C4B C5B 1.4200 . ?
C4B H4B 0.9500 . ?
C5B H5B 0.9500 . ?
C6 C7 1.421(6) . ?
C6 C10 1.435(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.412(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.433(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.455(6) . ?
C9 C14 1.492(6) . ?
C10 S1 1.709(4) . ?
S1 O11 1.407(4) . ?
S1 O12 1.411(4) . ?
S1 F13 1.579(4) . ?
C14 O15 1.463(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
O15 C16 1.344(5) . ?
C16 O17 1.206(6) . ?
C16 C18 1.498(7) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C10 Fe1 C4B 111.4(2) . . ?
C10 Fe1 C3B 119.2(3) . . ?
C4B Fe1 C3B 41.10(14) . . ?
C10 Fe1 C6 41.61(16) . . ?
C4B Fe1 C6 132.8(3) . . ?
C3B Fe1 C6 109.0(2) . . ?
C10 Fe1 C9 42.20(16) . . ?
C4B Fe1 C9 118.5(3) . . ?
C3B Fe1 C9 152.8(3) . . ?
C6 Fe1 C9 70.50(17) . . ?
C10 Fe1 C5B 132.6(3) . . ?
C4B Fe1 C5B 40.96(14) . . ?
C3B Fe1 C5B 68.79(18) . . ?
C6 Fe1 C5B 172.5(3) . . ?
C9 Fe1 C5B 108.0(2) . . ?
C10 Fe1 C2B 150.3(3) . . ?
C4B Fe1 C2B 68.68(17) . . ?
C3B Fe1 C2B 40.71(13) . . ?
C6 Fe1 C2B 115.1(3) . . ?
C9 Fe1 C2B 165.3(3) . . ?
C5B Fe1 C2B 68.26(17) . . ?
C10 Fe1 C1A 169.7(3) . . ?
C6 Fe1 C1A 129.8(3) . . ?
C9 Fe1 C1A 147.1(3) . . ?
C10 Fe1 C1B 169.3(3) . . ?
C4B Fe1 C1B 68.52(17) . . ?
C3B Fe1 C1B 68.35(17) . . ?
C6 Fe1 C1B 146.2(3) . . ?
C9 Fe1 C1B 127.7(3) . . ?
C5B Fe1 C1B 40.50(14) . . ?
C2B Fe1 C1B 40.35(13) . . ?
C10 Fe1 C5A 149.0(3) . . ?
C6 Fe1 C5A 168.6(3) . . ?
C9 Fe1 C5A 115.4(2) . . ?
C1A Fe1 C5A 40.25(11) . . ?
C10 Fe1 C2A 131.2(3) . . ?
C6 Fe1 C2A 108.2(2) . . ?
C9 Fe1 C2A 171.2(3) . . ?
C1A Fe1 C2A 40.23(11) . . ?
C5A Fe1 C2A 67.56(14) . . ?
C10 Fe1 C7 68.59(18) . . ?
C4B Fe1 C7 169.8(3) . . ?
C3B Fe1 C7 129.4(3) . . ?
C6 Fe1 C7 40.49(18) . . ?
C9 Fe1 C7 68.82(17) . . ?
C5B Fe1 C7 146.4(3) . . ?
C2B Fe1 C7 106.0(2) . . ?
C1A Fe1 C7 108.4(2) . . ?
C1B Fe1 C7 113.5(3) . . ?
C5A Fe1 C7 130.7(3) . . ?
C2A Fe1 C7 116.2(2) . . ?
C2A C1A C5A 108.0 . . ?
C2A C1A Fe1 70.1(2) . . ?
C5A C1A Fe1 70.0(2) . . ?
C2A C1A H1A 126.0 . . ?
C5A C1A H1A 126.0 . . ?
Fe1 C1A H1A 125.5 . . ?
C3A C2A C1A 108.0 . . ?
C3A C2A Fe1 70.2(2) . . ?
C1A C2A Fe1 69.7(2) . . ?
C3A C2A H2A 126.0 . . ?
C1A C2A H2A 126.0 . . ?
Fe1 C2A H2A 125.7 . . ?
C2A C3A C4A 108.0 . . ?
C2A C3A Fe1 69.7(2) . . ?
C4A C3A Fe1 69.9(2) . . ?
C2A C3A H3A 126.0 . . ?
C4A C3A H3A 126.0 . . ?
Fe1 C3A H3A 126.0 . . ?
C5A C4A C3A 108.0 . . ?
C5A C4A Fe1 69.6(3) . . ?
C3A C4A Fe1 70.0(2) . . ?
C5A C4A H4A 126.0 . . ?
C3A C4A H4A 126.0 . . ?
Fe1 C4A H4A 125.9 . . ?
C4A C5A C1A 108.0 . . ?
C4A C5A Fe1 70.2(3) . . ?
C1A C5A Fe1 69.7(2) . . ?
C4A C5A H5A 126.0 . . ?
C1A C5A H5A 126.0 . . ?
Fe1 C5A H5A 125.6 . . ?
C2B C1B C5B 108.0 . . ?
C2B C1B Fe1 69.5(3) . . ?
C5B C1B Fe1 68.9(3) . . ?
C2B C1B H1B 126.0 . . ?
C5B C1B H1B 126.0 . . ?
Fe1 C1B H1B 127.1 . . ?
C3B C2B C1B 108.0 . . ?
C3B C2B Fe1 68.6(3) . . ?
C1B C2B Fe1 70.1(3) . . ?
C3B C2B H2B 126.0 . . ?
C1B C2B H2B 126.0 . . ?
Fe1 C2B H2B 126.8 . . ?
C2B C3B C4B 108.0 . . ?
C2B C3B Fe1 70.7(3) . . ?
C4B C3B Fe1 69.1(3) . . ?
C2B C3B H3B 126.0 . . ?
C4B C3B H3B 126.0 . . ?
Fe1 C3B H3B 125.8 . . ?
C5B C4B C3B 108.0 . . ?
C5B C4B Fe1 70.3(3) . . ?
C3B C4B Fe1 69.8(3) . . ?
C5B C4B H4B 126.0 . . ?
C3B C4B H4B 126.0 . . ?
Fe1 C4B H4B 125.4 . . ?
C4B C5B C1B 108.0 . . ?
C4B C5B Fe1 68.7(3) . . ?
C1B C5B Fe1 70.6(3) . . ?
C4B C5B H5B 126.0 . . ?
C1B C5B H5B 126.0 . . ?
Fe1 C5B H5B 126.3 . . ?
C7 C6 C10 107.2(4) . . ?
C7 C6 Fe1 71.2(3) . . ?
C10 C6 Fe1 68.1(2) . . ?
C7 C6 H6 126.4 . . ?
C10 C6 H6 126.4 . . ?
Fe1 C6 H6 125.8 . . ?
C8 C7 C6 108.9(4) . . ?
C8 C7 Fe1 70.3(3) . . ?
C6 C7 Fe1 68.3(3) . . ?
C8 C7 H7 125.6 . . ?
C6 C7 H7 125.6 . . ?
Fe1 C7 H7 127.4 . . ?
C7 C8 C9 109.4(4) . . ?
C7 C8 Fe1 69.9(2) . . ?
C9 C8 Fe1 68.0(2) . . ?
C7 C8 H8 125.3 . . ?
C9 C8 H8 125.3 . . ?
Fe1 C8 H8 128.4 . . ?
C8 C9 C10 105.7(4) . . ?
C8 C9 C14 125.9(4) . . ?
C10 C9 C14 128.3(4) . . ?
C8 C9 Fe1 71.2(2) . . ?
C10 C9 Fe1 67.8(2) . . ?
C14 C9 Fe1 127.9(3) . . ?
C6 C10 C9 108.7(4) . . ?
C6 C10 S1 123.3(3) . . ?
C9 C10 S1 127.7(3) . . ?
C6 C10 Fe1 70.3(2) . . ?
C9 C10 Fe1 70.0(2) . . ?
S1 C10 Fe1 121.2(2) . . ?
O11 S1 O12 120.4(3) . . ?
O11 S1 F13 104.7(3) . . ?
O12 S1 F13 104.4(3) . . ?
O11 S1 C10 112.7(2) . . ?
O12 S1 C10 111.5(2) . . ?
F13 S1 C10 100.5(2) . . ?
O15 C14 C9 109.7(4) . . ?
O15 C14 H14A 109.7 . . ?
C9 C14 H14A 109.7 . . ?
O15 C14 H14B 109.7 . . ?
C9 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
C16 O15 C14 115.9(3) . . ?
O17 C16 O15 124.0(4) . . ?
O17 C16 C18 124.5(4) . . ?
O15 C16 C18 111.5(4) . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C5A C1A C2A C3A 0.0 . . . . ?
Fe1 C1A C2A C3A -60.0(2) . . . . ?
C5A C1A C2A Fe1 60.0(2) . . . . ?
C1A C2A C3A C4A 0.0 . . . . ?
Fe1 C2A C3A C4A -59.7(2) . . . . ?
C1A C2A C3A Fe1 59.7(2) . . . . ?
C2A C3A C4A C5A 0.0 . . . . ?
Fe1 C3A C4A C5A -59.5(2) . . . . ?
C2A C3A C4A Fe1 59.5(2) . . . . ?
C3A C4A C5A C1A 0.0 . . . . ?
Fe1 C4A C5A C1A -59.8(2) . . . . ?
C3A C4A C5A Fe1 59.8(2) . . . . ?
C2A C1A C5A C4A 0.0 . . . . ?
Fe1 C1A C5A C4A 60.1(2) . . . . ?
C2A C1A C5A Fe1 -60.1(2) . . . . ?
C5B C1B C2B C3B 0.0 . . . . ?
Fe1 C1B C2B C3B -58.3(3) . . . . ?
C5B C1B C2B Fe1 58.3(3) . . . . ?
C1B C2B C3B C4B 0.0 . . . . ?
Fe1 C2B C3B C4B -59.3(3) . . . . ?
C1B C2B C3B Fe1 59.3(3) . . . . ?
C2B C3B C4B C5B 0.0 . . . . ?
Fe1 C3B C4B C5B -60.2(3) . . . . ?
C2B C3B C4B Fe1 60.2(3) . . . . ?
C3B C4B C5B C1B 0.0 . . . . ?
Fe1 C4B C5B C1B -59.9(3) . . . . ?
C3B C4B C5B Fe1 59.9(3) . . . . ?
C2B C1B C5B C4B 0.0 . . . . ?
Fe1 C1B C5B C4B 58.7(3) . . . . ?
C2B C1B C5B Fe1 -58.7(3) . . . . ?
C10 C6 C7 C8 0.1(5) . . . . ?
Fe1 C6 C7 C8 -58.7(3) . . . . ?
C10 C6 C7 Fe1 58.9(3) . . . . ?
C6 C7 C8 C9 1.0(5) . . . . ?
Fe1 C7 C8 C9 -56.5(3) . . . . ?
C6 C7 C8 Fe1 57.5(3) . . . . ?
C7 C8 C9 C10 -1.6(5) . . . . ?
Fe1 C8 C9 C10 -59.3(3) . . . . ?
C7 C8 C9 C14 -178.6(4) . . . . ?
Fe1 C8 C9 C14 123.8(4) . . . . ?
C7 C8 C9 Fe1 57.6(3) . . . . ?
C7 C6 C10 C9 -1.2(5) . . . . ?
Fe1 C6 C10 C9 59.7(3) . . . . ?
C7 C6 C10 S1 -175.9(3) . . . . ?
Fe1 C6 C10 S1 -115.1(3) . . . . ?
C7 C6 C10 Fe1 -60.9(3) . . . . ?
C8 C9 C10 C6 1.7(5) . . . . ?
C14 C9 C10 C6 178.6(4) . . . . ?
Fe1 C9 C10 C6 -59.8(3) . . . . ?
C8 C9 C10 S1 176.2(3) . . . . ?
C14 C9 C10 S1 -7.0(7) . . . . ?
Fe1 C9 C10 S1 114.6(4) . . . . ?
C8 C9 C10 Fe1 61.6(3) . . . . ?
C14 C9 C10 Fe1 -121.6(4) . . . . ?
C6 C10 S1 O11 160.2(4) . . . . ?
C9 C10 S1 O11 -13.5(5) . . . . ?
Fe1 C10 S1 O11 74.5(3) . . . . ?
C6 C10 S1 O12 21.3(5) . . . . ?
C9 C10 S1 O12 -152.5(4) . . . . ?
Fe1 C10 S1 O12 -64.5(3) . . . . ?
C6 C10 S1 F13 -88.8(4) . . . . ?
C9 C10 S1 F13 97.4(4) . . . . ?
Fe1 C10 S1 F13 -174.6(2) . . . . ?
C8 C9 C14 O15 93.6(5) . . . . ?
C10 C9 C14 O15 -82.7(5) . . . . ?
Fe1 C9 C14 O15 -172.9(3) . . . . ?
C9 C14 O15 C16 -91.8(4) . . . . ?
C14 O15 C16 O17 2.2(7) . . . . ?
C14 O15 C16 C18 -177.0(4) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


