Cu-Catalyzed Enantioselective Ring Opening of Cyclic Diaryliodoniums toward the Synthesis of Chiral Diarylmethanes.
Li, Bin; Chao, Zengyin; Li, Chunyu; Gu, Zhenhua; Journal of the American Chemical Society 140 (2018) 9400–9403; doi:10.1021/jacs.8b05743

data_4132701
_publ_section_title
;
 Cu-Catalyzed Enantioselective Ring Opening of Cyclic Diaryliodoniums
 toward the Synthesis of Chiral Diarylmethanes.
;
_journal_issue                   30
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9400
_journal_page_last               9403
_journal_paper_doi               10.1021/jacs.8b05743
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C21 H24 I O2, C F3 O3 S'
_chemical_formula_sum            'C22 H24 F3 I O5 S'
_chemical_formula_weight         584.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-05-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.723(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.6006(5)
_cell_length_b                   20.3822(10)
_cell_length_c                   24.3422(13)
_cell_measurement_reflns_used    9801
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.0420
_cell_measurement_theta_min      2.4510
_cell_volume                     4694.9(4)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(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 1.000
_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    -40.00  59.00   1.00    3.00    --  -11.59  57.00  90.00   99
  2  \w     52.00  92.00   1.00    3.00    --   11.74 178.00 -60.00   40
  3  \w    -16.00  81.00   1.00    3.00    --   11.74  77.00-150.00   97
  4  \w    -81.00  13.00   1.00    3.00    --  -11.59 -57.00 -60.00   94
;
_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      0.0371287000
_diffrn_orient_matrix_UB_12      0.0082939000
_diffrn_orient_matrix_UB_13      0.0267909000
_diffrn_orient_matrix_UB_21      -0.0138093000
_diffrn_orient_matrix_UB_22      0.0337170000
_diffrn_orient_matrix_UB_23      -0.0058099000
_diffrn_orient_matrix_UB_31      -0.0636974000
_diffrn_orient_matrix_UB_32      -0.0024386000
_diffrn_orient_matrix_UB_33      0.0109960000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            34429
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.970
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.508
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60763
_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    1.653
_exptl_crystal_description       block
_exptl_crystal_F_000             2336
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.218
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     587
_refine_ls_number_reflns         8276
_refine_ls_number_restraints     78
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.1328
_refine_ls_R_factor_gt           0.0893
_refine_ls_shift/su_max          0.051
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0392P)^2^+191.7920P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2442
_refine_ls_wR_factor_ref         0.2420
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7037
_reflns_number_total             8276
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b05743_si_003.cif
_cod_data_source_block           7-176
_cod_database_code               4132701
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.852
_shelx_estimated_absorpt_t_min   0.828
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C15, C16
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C17, C18, C19
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C17, O2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 S1B, C22B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C16, C17
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 F2B, C22B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C15 \\sim C16: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004
C17 \\sim C18 \\sim C19: within 2A with sigma of 0.002 and sigma for terminal
atoms of 0.004
C17 \\sim O2: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004
S1B \\sim C22B: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004
C16 \\sim C17: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004
F2B \\sim C22B: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004
Uanis(C16) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C17) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C15B) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C16B) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O4B) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O1B) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
 C14B(H14B), C15(H15)
4.b Secondary CH2 refined with riding coordinates:
 C17B(H17A,H17B), C15B(H15A,H15B), C18(H18D,H18E), C16(H16A,H16B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C12(H12), C8B(H8B), C5(H5), C11B(H11B), C1B(H1B), C9(H9), C4B(H4B)
4.d Idealised Me refined as rotating group:
 C14(H14A,H14C,H14D), C12B(H12A,H12B,H12C), C20B(H20A,H20B,H20C), C21(H21A,
 H21B,H21C), C19B(H19A,H19B,H19C), C18B(H18A,H18B,H18C), C13(H13D,H13E,H13F),
 C13B(H13A,H13B,H13C), C20(H20D,H20E,H20F), C19(H19D,H19E,H19F)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.595
_oxdiff_exptl_absorpt_empirical_full_min 0.714