Iridium-Catalyzed Enantioselective Intramolecular Hydroarylation of Allylic Aryl Ethers Devoid of a Directing Group on the Aryl Group
Ohmura, Toshimichi; Kusaka, Satoshi; Suginome, Michinori; Chemical Communications  (2021) –; doi:10.1039/D1CC05684K

data_7129313
_publ_section_title
;
 Iridium-Catalyzed Enantioselective Intramolecular Hydroarylation of
 Allylic Aryl Ethers Devoid of a Directing Group on the Aryl Group
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC05684K
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_sum            'C12 H18 O2 Si'
_chemical_formula_weight         222.35
_chemical_name_systematic
(R)-3-methyl-5-(trimethylsilyl)-2,3-dihydrobenzofuran-3-ol
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-07-28 deposited with the CCDC.	2021-11-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   6.7361(17)
_cell_length_b                   21.906(6)
_cell_length_c                   26.843(7)
_cell_measurement_reflns_used    7682
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     3961.0(18)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      143(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0970
_diffrn_reflns_av_unetI/netI     0.1111
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            32323
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.488
_diffrn_reflns_theta_min         3.036
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.791
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.119
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1440
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hot hexane'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1515 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         9056
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.141
_refine_ls_R_factor_all          0.1287
_refine_ls_R_factor_gt           0.0903
_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^)+(0.0310P)^2^+0.9645P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1317
_refine_ls_wR_factor_ref         0.1464
_reflns_Friedel_coverage         0.771
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                6333
_reflns_number_total             9056
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc05684k2.cif
_cod_data_source_block           cKSS10_a_a_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7129313
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              68281