#------------------------------------------------------------------------------
#$Date: 2021-10-29 01:40:48 +0200 (vie 29 de oct de 2021) $
#$Revision: 270122 $
#$URL: svn://www.crystallography.net/cod/cif/7/70/86/7708626.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7708626
loop_
_publ_author_name
'Erb, William'
'Roisnel, Thierry'
_publ_section_title
;
 The chemistry of ferrocenesulfonyl fluoride revealed
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D1DT03492H
_journal_year                    2021
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C12 H9 F Fe O2 S'
_chemical_formula_sum            'C12 H9 F Fe O2 S'
_chemical_formula_weight         292.10
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2021-10-12 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;
_cell_angle_alpha                81.337(6)
_cell_angle_beta                 74.314(6)
_cell_angle_gamma                84.801(6)
_cell_formula_units_Z            2
_cell_length_a                   6.9415(12)
_cell_length_b                   9.1569(18)
_cell_length_c                   9.4381(18)
_cell_measurement_reflns_used    5096
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.4940
_cell_measurement_theta_min      2.2529
_cell_measurement_wavelength     0.710730
_cell_volume                     570.19(19)
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_molecular_graphics
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material
'CRYSCALC (T. Roisnel, local program, ver. 2021)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'APEXII Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_orient_matrix_UB_11      0.0608765
_diffrn_orient_matrix_UB_12      -0.0776709
_diffrn_orient_matrix_UB_13      -0.0652122
_diffrn_orient_matrix_UB_21      0.0512060
_diffrn_orient_matrix_UB_22      0.0787527
_diffrn_orient_matrix_UB_23      -0.0842916
_diffrn_orient_matrix_UB_31      0.1269790
_diffrn_orient_matrix_UB_32      -0.0013626
_diffrn_orient_matrix_UB_33      0.0310972
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9163
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.568
_diffrn_reflns_theta_min         2.975
_exptl_absorpt_coefficient_mu    1.502
_exptl_absorpt_correction_T_max  0.775
_exptl_absorpt_correction_T_min  0.676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_description       prism
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.940
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2602
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0264
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0359P)²+0.2906P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0701
_reflns_number_gt                2386
_reflns_number_total             2602
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1dt03492h2.cif
_cod_data_source_block           WE13761
_cod_database_code               7708626
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.8858(3) 0.7554(3) 0.4557(3) 0.0445(6) Uani 1 1 d . . . . .
H1 H 0.823822 0.742419 0.559344 0.053 Uiso 1 1 calc R U . . .
C2 C 0.9407(3) 0.6423(2) 0.3638(3) 0.0442(6) Uani 1 1 d . . . . .
H2 H 0.922498 0.539598 0.394088 0.053 Uiso 1 1 calc R U . . .
C3 C 1.0274(3) 0.7098(3) 0.2191(3) 0.0402(5) Uani 1 1 d . . . . .
H3 H 1.078614 0.660211 0.134065 0.048 Uiso 1 1 calc R U . . .
C4 C 1.0255(3) 0.8625(3) 0.2216(3) 0.0407(5) Uani 1 1 d . . . . .
H4 H 1.074530 0.934413 0.138711 0.049 Uiso 1 1 calc R U . . .
C5 C 0.9387(3) 0.8903(2) 0.3673(3) 0.0416(6) Uani 1 1 d . . . . .
H5 H 0.918877 0.984685 0.400819 0.050 Uiso 1 1 calc R U . . .
C6 C 0.5746(3) 0.91960(19) 0.1674(2) 0.0235(4) Uani 1 1 d . . . . .
H6 H 0.619974 1.000255 0.093198 0.028 Uiso 1 1 calc R U . . .
C7 C 0.4818(3) 0.92708(19) 0.3195(2) 0.0232(4) Uani 1 1 d . . . . .
H7 H 0.453221 1.014788 0.365478 0.028 Uiso 1 1 calc R U . . .
C8 C 0.4378(2) 0.77977(19) 0.3929(2) 0.0219(3) Uani 1 1 d . . . . .
C9 C 0.5036(2) 0.67936(19) 0.28568(19) 0.0213(3) Uani 1 1 d . . . . .
H9 H 0.493851 0.575042 0.303039 0.026 Uiso 1 1 calc R U . . .
C10 C 0.5870(3) 0.76624(19) 0.14703(19) 0.0208(3) Uani 1 1 d . . . . .
C11 C 0.3487(3) 0.7395(2) 0.5478(2) 0.0251(4) Uani 1 1 d . . . . .
C12 C 0.2733(3) 0.7049(2) 0.6759(2) 0.0336(4) Uani 1 1 d . . . . .
H12 H 0.212886 0.677178 0.778479 0.040 Uiso 1 1 calc R U . . .
O13 O 0.8388(3) 0.79586(18) -0.11254(17) 0.0460(4) Uani 1 1 d . . . . .
O14 O 0.7517(3) 0.54460(16) 0.00981(17) 0.0411(4) Uani 1 1 d . . . . .
F15 F 0.5210(2) 0.70928(15) -0.08868(14) 0.0457(3) Uani 1 1 d . . . . .
Fe1 Fe 0.73992(3) 0.79207(3) 0.29218(3) 0.01922(9) Uani 1 1 d . . . . .
S1 S 0.70094(7) 0.69747(5) -0.01597(5) 0.02758(12) Uani 1 1 d . . . . .
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_
_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 108.0(2) . . ?
C5 C1 Fe1 70.04(12) . . ?
C2 C1 Fe1 69.91(12) . . ?
C5 C1 H1 126.0 . . ?
C2 C1 H1 126.0 . . ?
Fe1 C1 H1 125.6 . . ?
C3 C2 C1 107.3(2) . . ?
C3 C2 Fe1 69.85(12) . . ?
C1 C2 Fe1 69.59(12) . . ?
C3 C2 H2 126.4 . . ?
C1 C2 H2 126.4 . . ?
Fe1 C2 H2 125.8 . . ?
C4 C3 C2 108.4(2) . . ?
C4 C3 Fe1 70.05(12) . . ?
C2 C3 Fe1 69.83(12) . . ?
C4 C3 H3 125.8 . . ?
C2 C3 H3 125.8 . . ?
Fe1 C3 H3 125.9 . . ?
C5 C4 C3 107.9(2) . . ?
C5 C4 Fe1 69.87(12) . . ?
C3 C4 Fe1 69.84(12) . . ?
C5 C4 H4 126.0 . . ?
C3 C4 H4 126.0 . . ?
Fe1 C4 H4 125.8 . . ?
C4 C5 C1 108.4(2) . . ?
C4 C5 Fe1 70.14(12) . . ?
C1 C5 Fe1 69.76(12) . . ?
C4 C5 H5 125.8 . . ?
C1 C5 H5 125.8 . . ?
Fe1 C5 H5 125.9 . . ?
C7 C6 C10 106.69(15) . . ?
C7 C6 Fe1 70.82(10) . . ?
C10 C6 Fe1 67.72(9) . . ?
C7 C6 H6 126.7 . . ?
C10 C6 H6 126.7 . . ?
Fe1 C6 H6 126.3 . . ?
C6 C7 C8 108.69(15) . . ?
C6 C7 Fe1 68.78(10) . . ?
C8 C7 Fe1 69.53(10) . . ?
C6 C7 H7 125.7 . . ?
C8 C7 H7 125.7 . . ?
Fe1 C7 H7 127.6 . . ?
C9 C8 C11 125.49(16) . . ?
C9 C8 C7 108.39(15) . . ?
C11 C8 C7 126.10(16) . . ?
C9 C8 Fe1 68.65(10) . . ?
C11 C8 Fe1 126.17(12) . . ?
C7 C8 Fe1 69.60(10) . . ?
C8 C9 C10 106.61(15) . . ?
C8 C9 Fe1 70.61(10) . . ?
C10 C9 Fe1 67.85(9) . . ?
C8 C9 H9 126.7 . . ?
C10 C9 H9 126.7 . . ?
Fe1 C9 H9 126.4 . . ?
C9 C10 C6 109.62(15) . . ?
C9 C10 S1 125.29(13) . . ?
C6 C10 S1 124.93(14) . . ?
C9 C10 Fe1 70.66(10) . . ?
C6 C10 Fe1 70.51(10) . . ?
S1 C10 Fe1 121.63(9) . . ?
C12 C11 C8 179.1(2) . . ?
C11 C12 H12 180.0 . . ?
C10 Fe1 C6 41.77(7) . . ?
C10 Fe1 C9 41.49(7) . . ?
C6 Fe1 C9 70.29(7) . . ?
C10 Fe1 C1 163.66(9) . . ?
C6 Fe1 C1 153.21(9) . . ?
C9 Fe1 C1 125.27(9) . . ?
C10 Fe1 C5 154.91(9) . . ?
C6 Fe1 C5 118.94(8) . . ?
C9 Fe1 C5 162.28(9) . . ?
C1 Fe1 C5 40.20(10) . . ?
C10 Fe1 C2 126.61(9) . . ?
C6 Fe1 C2 164.34(10) . . ?
C9 Fe1 C2 107.58(8) . . ?
C1 Fe1 C2 40.50(10) . . ?
C5 Fe1 C2 67.78(9) . . ?
C10 Fe1 C3 108.99(8) . . ?
C6 Fe1 C3 126.61(9) . . ?
C9 Fe1 C3 121.04(8) . . ?
C1 Fe1 C3 67.63(9) . . ?
C5 Fe1 C3 67.32(9) . . ?
C2 Fe1 C3 40.32(10) . . ?
C10 Fe1 C4 120.96(9) . . ?
C6 Fe1 C4 107.49(8) . . ?
C9 Fe1 C4 155.94(9) . . ?
C1 Fe1 C4 67.56(10) . . ?
C5 Fe1 C4 39.99(10) . . ?
C2 Fe1 C4 67.79(9) . . ?
C3 Fe1 C4 40.11(9) . . ?
C10 Fe1 C8 68.64(7) . . ?
C6 Fe1 C8 68.97(7) . . ?
C9 Fe1 C8 40.74(7) . . ?
C1 Fe1 C8 107.38(8) . . ?
C5 Fe1 C8 125.41(9) . . ?
C2 Fe1 C8 120.14(9) . . ?
C3 Fe1 C8 155.43(9) . . ?
C4 Fe1 C8 162.41(9) . . ?
C10 Fe1 C7 68.61(7) . . ?
C6 Fe1 C7 40.39(7) . . ?
C9 Fe1 C7 69.11(7) . . ?
C1 Fe1 C7 119.48(9) . . ?
C5 Fe1 C7 107.27(8) . . ?
C2 Fe1 C7 154.51(10) . . ?
C3 Fe1 C7 162.98(9) . . ?
C4 Fe1 C7 125.50(8) . . ?
C8 Fe1 C7 40.87(7) . . ?
O13 S1 O14 121.31(10) . . ?
O13 S1 F15 104.17(10) . . ?
O14 S1 F15 105.58(9) . . ?
O13 S1 C10 111.50(9) . . ?
O14 S1 C10 111.12(9) . . ?
F15 S1 C10 100.55(8) . . ?
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(4) . ?
C1 C2 1.411(3) . ?
C1 Fe1 2.037(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.407(4) . ?
C2 Fe1 2.041(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.401(3) . ?
C3 Fe1 2.041(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(3) . ?
C4 Fe1 2.044(2) . ?
C4 H4 0.9500 . ?
C5 Fe1 2.040(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.414(3) . ?
C6 C10 1.438(2) . ?
C6 Fe1 2.0348(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.439(2) . ?
C7 Fe1 2.0616(17) . ?
C7 H7 0.9500 . ?
C8 C9 1.426(2) . ?
C8 C11 1.430(3) . ?
C8 Fe1 2.0607(17) . ?
C9 C10 1.429(2) . ?
C9 Fe1 2.0348(17) . ?
C9 H9 0.9500 . ?
C10 S1 1.7124(18) . ?
C10 Fe1 1.9972(17) . ?
C11 C12 1.187(3) . ?
C12 H12 0.9500 . ?
O13 S1 1.4124(16) . ?
O14 S1 1.4132(15) . ?
F15 S1 1.5684(13) . ?
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 59.96(14) . . . . ?
C5 C1 C2 Fe1 -59.92(14) . . . . ?
C1 C2 C3 C4 -0.2(2) . . . . ?
Fe1 C2 C3 C4 59.63(14) . . . . ?
C1 C2 C3 Fe1 -59.80(14) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
Fe1 C3 C4 C5 59.73(14) . . . . ?
C2 C3 C4 Fe1 -59.49(14) . . . . ?
C3 C4 C5 C1 -0.2(2) . . . . ?
Fe1 C4 C5 C1 59.50(14) . . . . ?
C3 C4 C5 Fe1 -59.71(14) . . . . ?
C2 C1 C5 C4 0.1(2) . . . . ?
Fe1 C1 C5 C4 -59.74(14) . . . . ?
C2 C1 C5 Fe1 59.84(14) . . . . ?
C10 C6 C7 C8 0.27(18) . . . . ?
Fe1 C6 C7 C8 -58.17(12) . . . . ?
C10 C6 C7 Fe1 58.44(11) . . . . ?
C6 C7 C8 C9 -0.07(19) . . . . ?
Fe1 C7 C8 C9 -57.79(12) . . . . ?
C6 C7 C8 C11 178.25(16) . . . . ?
Fe1 C7 C8 C11 120.53(17) . . . . ?
C6 C7 C8 Fe1 57.72(12) . . . . ?
C11 C8 C9 C10 -178.49(16) . . . . ?
C7 C8 C9 C10 -0.15(18) . . . . ?
Fe1 C8 C9 C10 -58.52(11) . . . . ?
C11 C8 C9 Fe1 -119.97(17) . . . . ?
C7 C8 C9 Fe1 58.37(12) . . . . ?
C8 C9 C10 C6 0.32(19) . . . . ?
Fe1 C9 C10 C6 -59.97(12) . . . . ?
C8 C9 C10 S1 175.93(13) . . . . ?
Fe1 C9 C10 S1 115.63(14) . . . . ?
C8 C9 C10 Fe1 60.30(11) . . . . ?
C7 C6 C10 C9 -0.37(19) . . . . ?
Fe1 C6 C10 C9 60.06(12) . . . . ?
C7 C6 C10 S1 -175.99(13) . . . . ?
Fe1 C6 C10 S1 -115.56(14) . . . . ?
C7 C6 C10 Fe1 -60.43(11) . . . . ?
C9 C10 S1 O13 -154.62(15) . . . . ?
C6 C10 S1 O13 20.33(18) . . . . ?
Fe1 C10 S1 O13 -66.93(14) . . . . ?
C9 C10 S1 O14 -15.95(18) . . . . ?
C6 C10 S1 O14 159.00(15) . . . . ?
Fe1 C10 S1 O14 71.74(13) . . . . ?
C9 C10 S1 F15 95.44(16) . . . . ?
C6 C10 S1 F15 -89.61(15) . . . . ?
Fe1 C10 S1 F15 -176.87(10) . . . . ?
