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_7128032
_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_formula_moiety         'C21 H19 I O2 S2'
_chemical_formula_sum            'C21 H19 I O2 S2'
_chemical_formula_weight         494.38
_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             2020-10-12
_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                   8.1814(3)
_cell_length_b                   11.4924(4)
_cell_length_c                   21.1523(8)
_cell_measurement_reflns_used    10713
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      29.0480
_cell_measurement_theta_min      2.5960
_cell_volume                     1988.82(13)
_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  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.923
_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    -20.00  30.00   1.00    2.01    --  -11.27 -99.00 -30.00   50
  2  \w    -36.00  63.00   1.00    2.01    --  -11.27  37.00-180.00   99
  3  \w    -12.00  86.00   1.00    2.01    --   11.90  37.00-120.00   98
  4  \w    -20.00  23.00   1.00    2.01    --   11.90 -99.00  60.00   43
  5  \w     -8.00  17.00   1.00    2.01    --   11.90-113.00  82.00   25
  6  \w    -63.00  32.00   1.00    2.01    --   11.90 -37.00-120.00   95
;
_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      -0.0690740000
_diffrn_orient_matrix_UB_12      -0.0002801000
_diffrn_orient_matrix_UB_13      -0.0202414000
_diffrn_orient_matrix_UB_21      -0.0509825000
_diffrn_orient_matrix_UB_22      0.0134955000
_diffrn_orient_matrix_UB_23      0.0261216000
_diffrn_orient_matrix_UB_31      0.0112075000
_diffrn_orient_matrix_UB_32      0.0602442000
_diffrn_orient_matrix_UB_33      -0.0059169000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            21959
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.896
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.641
_diffrn_reflns_theta_min         1.926
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.833
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25211
_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    1.651
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.733
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details
;
 Flack x determined using 1831 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.016(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         5022
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0288
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0231P)^2^+0.1079P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0539
_refine_ls_wR_factor_ref         0.0562
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.861
_reflns_number_gt                4708
_reflns_number_total             5022
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc00171j2.cif
_cod_data_source_block           8-149_2
_cod_depositor_comments
'Adding full bibliography for 7128032--7128034.cif.'
_cod_database_code               7128032
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C3(H3), C4(H4), C11(H11), C12(H12), C13(H13), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              65198
_shelx_hkl_checksum              49227
_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 2.743
_oxdiff_exptl_absorpt_empirical_full_min 0.519