Aryloxymethyltrifluoroborates for Rhodium-Catalyzed Asymmetric Conjugate Arylation. o-Methoxyarylation through 1,4-Rhodium Shift.
Ming, Jialin; Hayashi, Tamio; Organic letters 18 (2016) 6452–6455; doi:10.1021/acs.orglett.6b03347

data_1555981
_publ_section_title
;
 Aryloxymethyltrifluoroborates for Rhodium-Catalyzed Asymmetric Conjugate
 Arylation. o-Methoxyarylation through 1,4-Rhodium Shift.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6452
_journal_page_last               6455
_journal_paper_doi               10.1021/acs.orglett.6b03347
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H19 Br O2'
_chemical_formula_sum            'C22 H19 Br O2'
_chemical_formula_weight         395.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 95.961(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.8971(6)
_cell_length_b                   5.9845(3)
_cell_length_c                   12.3079(7)
_cell_measurement_reflns_used    1797
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.432
_cell_measurement_theta_min      3.611
_cell_volume                     871.56(8)
_computing_cell_refinement
'SHELXTL, Acta Cryst., Sect. A 2008, 64, 112-122.'
_computing_data_collection       'APEX3 v2015.5.2'
_computing_data_reduction        'Saint, APEX v2014.11.0.'
_computing_molecular_graphics    Ortep3
_computing_publication_material  'APEX3 v2015.5.2'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT, Acta Cryst., Sect. A 2015, A71, 3-8.'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker AXS D8 Venture '
_diffrn_measurement_method       'profile data from \q/2\q scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13071
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.432
_diffrn_reflns_theta_min         3.611
_exptl_absorpt_coefficient_mu    3.304
_exptl_absorpt_correction_T_max  0.764
_exptl_absorpt_correction_T_min  0.370
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_description       plate
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.376
_exptl_crystal_size_mid          0.146
_exptl_crystal_size_min          0.086
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.658
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Flack x determined using 1425 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.059(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3380
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0264
_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^)+(0.0246P)^2^+0.8231P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0694
_refine_ls_wR_factor_ref         0.0696
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_full    0.965
_reflns_Friedel_fraction_max     0.950
_reflns_number_gt                3347
_reflns_number_total             3380
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03347_si_001.cif
_cod_data_source_block           g198
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1555981
_shelx_estimated_absorpt_t_min   0.370
_shelx_estimated_absorpt_t_max   0.764
_shelx_res_checksum              4311
_shelx_hkl_checksum              65638