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#$Date: 2023-05-04 08:27:32 +0300 (Thu, 04 May 2023) $
#$Revision: 282981 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/29/7712936.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_7712936
loop_
_publ_author_name
'Wen, Min'
'Erb, William'
'Mongin, Florence'
'Hurvois, Jean-Pierre'
'Halauko, Yury S.'
'Ivashkevich, Oleg A.'
'Matulis, Vadim E.'
'Blot, Marielle'
'Roisnel, Thierry'
_publ_section_title
;
 From ferrocene to decasubstituted enantiopure ferrocene-1,1'-disulfoxide
 derivatives.
;
_journal_issue                   12
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              3725
_journal_page_last               3737
_journal_paper_doi               10.1039/d2dt03456e
_journal_volume                  52
_journal_year                    2023
_chemical_absolute_configuration rm/ad/rmad/syn/unk/.
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C18 H26 Fe O2 S2'
_chemical_formula_sum            'C18 H26 Fe O2 S2'
_chemical_formula_weight         394.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2022-08-30 deposited with the CCDC.	2023-03-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.022(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   18.440(3)
_cell_length_b                   10.1792(16)
_cell_length_c                   5.9928(9)
_cell_measurement_reflns_used    8627
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      27.4966
_cell_measurement_theta_min      2.2996
_cell_measurement_wavelength     0.710730
_cell_volume                     1095.9(3)
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2021)'
_computing_structure_refinement  'SHELXL-2019_2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      250(2)
_diffrn_detector                 CMOS-PHOTON70
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_orient_matrix_UB_11      -0.0006942
_diffrn_orient_matrix_UB_12      -0.0891205
_diffrn_orient_matrix_UB_13      0.0696983
_diffrn_orient_matrix_UB_21      -0.0350522
_diffrn_orient_matrix_UB_22      0.0327958
_diffrn_orient_matrix_UB_23      0.0927368
_diffrn_orient_matrix_UB_31      -0.0432310
_diffrn_orient_matrix_UB_32      -0.0251601
_diffrn_orient_matrix_UB_33      -0.1260002
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            7342
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         4.004
_diffrn_source_current           1.00
_diffrn_source_power             50.0
_diffrn_source_voltage           50.00
_exptl_absorpt_coefficient_mu    0.884
_exptl_absorpt_correction_T_max  0.845
_exptl_absorpt_correction_T_min  0.739
_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    1.195
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
;
Flack x determined using 925 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.006(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     108
_refine_ls_number_reflns         2220
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0330
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0731P)²+1.0477P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.0991
_reflns_Friedel_coverage         0.725
_reflns_Friedel_fraction_full    0.818
_reflns_Friedel_fraction_max     0.779
_reflns_number_gt                2213
_reflns_number_total             2220
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2dt03456e2.cif
_cod_data_source_block           MW509
_cod_original_cell_volume        1096.0(3)
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               7712936
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -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
Fe1 Fe 0.500000 0.75045(4) 1.000000 0.01826(19) Uani 1 2 d S T P . .
C1 C 0.39240(17) 0.7559(5) 0.8134(6) 0.0253(6) Uani 1 1 d . . . . .
H1 H 0.377313 0.757350 0.651067 0.030 Uiso 1 1 calc R U . . .
C2 C 0.4060(2) 0.8657(5) 0.9576(8) 0.0315(9) Uani 1 1 d . . . . .
H2 H 0.401200 0.954731 0.909088 0.038 Uiso 1 1 calc R U . . .
C3 C 0.4285(2) 0.8218(5) 1.1902(8) 0.0317(9) Uani 1 1 d . . . . .
H3 H 0.440956 0.876485 1.321722 0.038 Uiso 1 1 calc R U . . .
C4 C 0.4288(2) 0.6833(4) 1.1901(6) 0.0238(7) Uani 1 1 d . . . . .
H4 H 0.441961 0.628016 1.320663 0.029 Uiso 1 1 calc R U . . .
C5 C 0.4053(2) 0.6410(4) 0.9547(6) 0.0205(7) Uani 1 1 d . . . . .
S1 S 0.40120(5) 0.47744(9) 0.85823(14) 0.0228(2) Uani 1 1 d . . . . .
O6 O 0.40747(19) 0.4828(3) 0.6124(5) 0.0371(7) Uani 1 1 d . . . . .
C7 C 0.3028(2) 0.4389(4) 0.8533(6) 0.0258(7) Uani 1 1 d . . . . .
C8 C 0.2507(2) 0.5335(6) 0.6982(7) 0.0399(10) Uani 1 1 d . . . . .
H8A H 0.264563 0.539213 0.550048 0.060 Uiso 1 1 calc R U . . .
H8B H 0.254452 0.620600 0.769492 0.060 Uiso 1 1 calc R U . . .
H8C H 0.199361 0.501559 0.675168 0.060 Uiso 1 1 calc R U . . .
C9 C 0.2936(2) 0.4432(5) 1.0988(7) 0.0359(10) Uani 1 1 d . . . . .
H9A H 0.242504 0.418774 1.102709 0.054 Uiso 1 1 calc R U . . .
H9B H 0.303979 0.532224 1.159855 0.054 Uiso 1 1 calc R U . . .
H9C H 0.328437 0.381323 1.192212 0.054 Uiso 1 1 calc R U . . .
C10 C 0.2923(3) 0.3006(5) 0.7580(9) 0.0425(11) Uani 1 1 d . . . . .
H10A H 0.331950 0.243949 0.843471 0.064 Uiso 1 1 calc R U . . .
H10B H 0.294340 0.301645 0.596047 0.064 Uiso 1 1 calc R U . . .
H10C H 0.243875 0.266772 0.772984 0.064 Uiso 1 1 calc R U . . .
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'
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 Fe1 C5 113.7(2) . 2_657 ?
C5 Fe1 C4 112.50(15) . 2_657 ?
C5 Fe1 C4 41.51(14) 2_657 2_657 ?
C5 Fe1 C4 41.51(15) . . ?
C5 Fe1 C4 112.50(15) 2_657 . ?
C4 Fe1 C4 140.9(2) 2_657 . ?
C5 Fe1 C1 41.04(15) . . ?
C5 Fe1 C1 141.61(17) 2_657 . ?
C4 Fe1 C1 111.76(15) 2_657 . ?
C4 Fe1 C1 69.35(14) . . ?
C5 Fe1 C1 141.61(17) . 2_657 ?
C5 Fe1 C1 41.04(15) 2_657 2_657 ?
C4 Fe1 C1 69.35(14) 2_657 2_657 ?
C4 Fe1 C1 111.76(15) . 2_657 ?
C1 Fe1 C1 176.9(3) . 2_657 ?
C5 Fe1 C2 67.85(14) . . ?
C5 Fe1 C2 178.4(2) 2_657 . ?
C4 Fe1 C2 138.68(17) 2_657 . ?
C4 Fe1 C2 68.30(18) . . ?
C1 Fe1 C2 39.86(18) . . ?
C1 Fe1 C2 137.46(18) 2_657 . ?
C5 Fe1 C2 178.39(19) . 2_657 ?
C5 Fe1 C2 67.85(14) 2_657 2_657 ?
C4 Fe1 C2 68.30(18) 2_657 2_657 ?
C4 Fe1 C2 138.68(17) . 2_657 ?
C1 Fe1 C2 137.46(18) . 2_657 ?
C1 Fe1 C2 39.86(18) 2_657 2_657 ?
C2 Fe1 C2 110.6(3) . 2_657 ?
C5 Fe1 C3 68.28(16) . . ?
C5 Fe1 C3 139.06(16) 2_657 . ?
C4 Fe1 C3 178.9(2) 2_657 . ?
C4 Fe1 C3 40.19(15) . . ?
C1 Fe1 C3 68.29(16) . . ?
C1 Fe1 C3 110.54(16) 2_657 . ?
C2 Fe1 C3 40.72(19) . . ?
C2 Fe1 C3 110.90(18) 2_657 . ?
C5 Fe1 C3 139.06(17) . 2_657 ?
C5 Fe1 C3 68.28(16) 2_657 2_657 ?
C4 Fe1 C3 40.19(15) 2_657 2_657 ?
C4 Fe1 C3 178.9(2) . 2_657 ?
C1 Fe1 C3 110.55(16) . 2_657 ?
C1 Fe1 C3 68.29(16) 2_657 2_657 ?
C2 Fe1 C3 110.90(18) . 2_657 ?
C2 Fe1 C3 40.72(19) 2_657 2_657 ?
C3 Fe1 C3 138.7(3) . 2_657 ?
C2 C1 C5 107.7(3) . . ?
C2 C1 Fe1 70.6(2) . . ?
C5 C1 Fe1 69.1(2) . . ?
C2 C1 H1 126.1 . . ?
C5 C1 H1 126.1 . . ?
Fe1 C1 H1 125.7 . . ?
C1 C2 C3 108.9(4) . . ?
C1 C2 Fe1 69.6(2) . . ?
C3 C2 Fe1 69.6(2) . . ?
C1 C2 H2 125.6 . . ?
C3 C2 H2 125.6 . . ?
Fe1 C2 H2 126.8 . . ?
C4 C3 C2 108.2(4) . . ?
C4 C3 Fe1 69.2(2) . . ?
C2 C3 Fe1 69.6(2) . . ?
C4 C3 H3 125.9 . . ?
C2 C3 H3 125.9 . . ?
Fe1 C3 H3 126.8 . . ?
C3 C4 C5 107.4(4) . . ?
C3 C4 Fe1 70.6(2) . . ?
C5 C4 Fe1 69.1(2) . . ?
C3 C4 H4 126.3 . . ?
C5 C4 H4 126.3 . . ?
Fe1 C4 H4 125.5 . . ?
C1 C5 C4 107.9(3) . . ?
C1 C5 S1 126.2(3) . . ?
C4 C5 S1 125.8(3) . . ?
C1 C5 Fe1 69.8(2) . . ?
C4 C5 Fe1 69.4(2) . . ?
S1 C5 Fe1 122.25(19) . . ?
O6 S1 C5 106.27(18) . . ?
O6 S1 C7 106.48(18) . . ?
C5 S1 C7 100.09(18) . . ?
C10 C7 C9 111.1(3) . . ?
C10 C7 C8 110.4(4) . . ?
C9 C7 C8 112.4(4) . . ?
C10 C7 S1 104.1(3) . . ?
C9 C7 S1 107.5(2) . . ?
C8 C7 S1 111.0(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
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 C5 2.038(4) . ?
Fe1 C5 2.038(4) 2_657 ?
Fe1 C4 2.041(4) 2_657 ?
Fe1 C4 2.041(4) . ?
Fe1 C1 2.047(3) . ?
Fe1 C1 2.047(3) 2_657 ?
Fe1 C2 2.060(4) . ?
Fe1 C2 2.060(4) 2_657 ?
Fe1 C3 2.060(4) . ?
Fe1 C3 2.060(4) 2_657 ?
C1 C2 1.400(6) . ?
C1 C5 1.432(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.434(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.409(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.445(5) . ?
C4 H4 0.9500 . ?
C5 S1 1.758(4) . ?
S1 O6 1.504(3) . ?
S1 C7 1.851(4) . ?
C7 C10 1.515(6) . ?
C7 C9 1.519(5) . ?
C7 C8 1.520(6) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
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 0.7(4) . . . . ?
Fe1 C1 C2 C3 -58.7(3) . . . . ?
C5 C1 C2 Fe1 59.4(2) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
Fe1 C2 C3 C4 -58.6(3) . . . . ?
C1 C2 C3 Fe1 58.6(3) . . . . ?
C2 C3 C4 C5 -0.7(5) . . . . ?
Fe1 C3 C4 C5 -59.6(3) . . . . ?
C2 C3 C4 Fe1 58.9(3) . . . . ?
C2 C1 C5 C4 -1.1(4) . . . . ?
Fe1 C1 C5 C4 59.1(2) . . . . ?
C2 C1 C5 S1 -176.1(3) . . . . ?
Fe1 C1 C5 S1 -115.8(3) . . . . ?
C2 C1 C5 Fe1 -60.3(2) . . . . ?
C3 C4 C5 C1 1.2(4) . . . . ?
Fe1 C4 C5 C1 -59.4(2) . . . . ?
C3 C4 C5 S1 176.2(3) . . . . ?
Fe1 C4 C5 S1 115.6(3) . . . . ?
C3 C4 C5 Fe1 60.6(3) . . . . ?
C1 C5 S1 O6 18.5(4) . . . . ?
C4 C5 S1 O6 -155.6(3) . . . . ?
Fe1 C5 S1 O6 -68.9(3) . . . . ?
C1 C5 S1 C7 -92.1(3) . . . . ?
C4 C5 S1 C7 93.8(3) . . . . ?
Fe1 C5 S1 C7 -179.6(2) . . . . ?
O6 S1 C7 C10 66.4(3) . . . . ?
C5 S1 C7 C10 176.8(3) . . . . ?
O6 S1 C7 C9 -175.7(3) . . . . ?
C5 S1 C7 C9 -65.3(3) . . . . ?
O6 S1 C7 C8 -52.4(3) . . . . ?
C5 S1 C7 C8 58.0(3) . . . . ?
