Enantioselective preparation of atropisomeric biaryl trifluoromethylsulfanes via ring-opening of cyclic diaryliodoniums.
Duan, Longhui; Wang, Zhonggui; Zhao, Kun; Gu, Zhenhua; Chemical communications (Cambridge, England) 57 (2021) 3881–3884; doi:10.1039/d1cc00171j

data_7128033
_publ_section_title
;
 Enantioselective preparation of atropisomeric biaryl
 trifluoromethylsulfanes via ring-opening of cyclic diaryliodoniums.
;
_journal_issue                   32
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3881
_journal_page_last               3884
_journal_paper_doi               10.1039/d1cc00171j
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C33 H26 F3 O4 P S2'
_chemical_formula_sum            'C33 H26 F3 O4 P S2'
_chemical_formula_weight         638.63
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-11-09
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_audit_update_record
;
2020-12-16 deposited with the CCDC.	2021-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1979(2)
_cell_length_b                   13.5767(2)
_cell_length_c                   24.3814(4)
_cell_measurement_reflns_used    7024
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.3100
_cell_measurement_theta_min      3.6100
_cell_volume                     3044.68(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -68.00  21.00   1.00    1.00    --  -40.73  57.00-150.00   89
  2  \w     24.00  73.00   1.00    1.00    --   40.73-125.00  90.00   49
  3  \w     35.00 114.00   1.00    1.00    --   40.73  57.00-150.00   79
  4  \w     31.00  92.00   1.00    1.00    --  106.95 -94.00 -60.00   61
  5  \w    105.00 175.00   1.00    1.00    --  106.95  45.00  60.00   70
  6  \w     85.00 178.00   1.00    1.00    --  106.95  30.00 150.00   93
  7  \w     72.00 100.00   1.00    1.00    --  106.95 -94.00  90.00   28
  8  \w     31.00 133.00   1.00    1.00    --  106.95 -30.00 -30.00  102
  9  \w     35.00  66.00   1.00    1.00    --  106.95-125.00 -60.00   31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0483704000
_diffrn_orient_matrix_UB_12      -0.0604851000
_diffrn_orient_matrix_UB_13      -0.0502786000
_diffrn_orient_matrix_UB_21      -0.1120988000
_diffrn_orient_matrix_UB_22      0.0801324000
_diffrn_orient_matrix_UB_23      -0.0145016000
_diffrn_orient_matrix_UB_31      0.1145553000
_diffrn_orient_matrix_UB_32      0.0529541000
_diffrn_orient_matrix_UB_33      -0.0354296000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            10913
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.642
_diffrn_reflns_theta_min         3.626
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.564
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.17344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_description       needle
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 2170 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.015(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         5938
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0561P)^2^+0.6425P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1112
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.947
_reflns_number_gt                5612
_reflns_number_total             5938
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc00171j2.cif
_cod_data_source_block           9-55-2
_cod_depositor_comments
'Adding full bibliography for 7128032--7128034.cif.'
_cod_database_code               7128033
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C16(H16),
 C17(H17), C18(H18), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C28(H28),
  C29(H29), C31(H31), C32(H32)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C33(H33A,H33B,H33C)
;
_shelx_res_checksum              98574
_shelx_hkl_checksum              43253
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.204
_oxdiff_exptl_absorpt_empirical_full_min 0.446