Chiral Cyclic Ligand-Enabled Iridium-Catalyzed Asymmetric Arylation of Unactivated Racemic Allylic Alcohols with Anilines.
Tian, Hua; Zhang, Pengxiang; Peng, Fei; Yang, Haijun; Fu, Hua; Organic letters 19 (2017) 3775–3778; doi:10.1021/acs.orglett.7b01631

data_1547105
_publ_section_title
;
 Chiral Cyclic Ligand-Enabled Iridium-Catalyzed Asymmetric Arylation of
 Unactivated Racemic Allylic Alcohols with Anilines.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3775
_journal_page_last               3778
_journal_paper_doi               10.1021/acs.orglett.7b01631
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C24 H26 N2 O2 S'
_chemical_formula_weight         406.53
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3681(3)
_cell_length_b                   9.6820(3)
_cell_length_c                   23.6969(7)
_cell_measurement_reflns_used    9022
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      68.2915
_cell_measurement_theta_min      3.7305
_cell_volume                     2149.35(11)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            12304
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.289
_diffrn_reflns_theta_min         3.730
_exptl_absorpt_coefficient_mu    1.507
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 1468 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.032(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         3897
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0303
_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^)+(0.0470P)^2^+0.0953P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0785
_refine_ls_wR_factor_ref         0.0797
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                3664
_reflns_number_total             3897
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01631_si_002.cif
_cod_data_source_block           cu_20170406_yjp_0m
_cod_original_cell_volume        2149.36(11)
_cod_database_code               1547105
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              35523
_shelx_hkl_checksum              63684