Asymmetric Synthesis of Allylic Fluorides via Fluorination of Racemic Allylic Trichloroacetimidates Catalyzed by a Chiral Diene-Iridium Complex
Mixdorf, Jason C.; Sorlin, Alexandre M.; Zhang, Qi; Nguyen, Hien M.; ACS Catalysis 8 (2017) 790–; doi:10.1021/acscatal.7b03786

data_4514328
_publ_section_title
;
 Asymmetric Synthesis of Allylic Fluorides via Fluorination of Racemic
 Allylic Trichloroacetimidates Catalyzed by a Chiral Diene-Iridium Complex
;
_journal_issue                   2
_journal_name_full               'ACS Catalysis'
_journal_page_first              790
_journal_paper_doi               10.1021/acscatal.7b03786
_journal_volume                  8
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H27 F O2'
_chemical_formula_sum            'C22 H27 F O2'
_chemical_formula_weight         342.43
_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   geom
_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                   5.9526(5)
_cell_length_b                   9.1966(7)
_cell_length_c                   33.092(3)
_cell_measurement_reflns_used    8753
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      35.83
_cell_measurement_theta_min      2.47
_cell_volume                     1811.6(3)
_computing_cell_refinement       'ApexII (Bruker-AXS, 2015)'
_computing_data_collection       'ApexII (Bruker-AXS, 2015)'
_computing_data_reduction        'ApexII (Bruker-AXS, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Shelxt, ApexII (Bruker-AXS, 2015)'
_diffrn_ambient_temperature      160(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD-APEXII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       55
_diffrn_reflns_limit_l_min       -55
_diffrn_reflns_number            151098
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.300
_diffrn_reflns_theta_min         2.298
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.7086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sortav, ApexII(Bruker-ASX, 2015)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_description       rod
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 3056 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         8753
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0405
_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^)+(0.0637P)^2^+0.0970P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1072
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                7711
_reflns_number_total             8753
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs7b03786_si_004.cif
_cod_data_source_block           ngu177
_cod_depositor_comments
'Adding full bibliography for 4514324--4514328.cif.'
_cod_database_code               4514328
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.972
_shelx_estimated_absorpt_t_max   0.989
_shelx_res_checksum              27850
_shelx_hkl_checksum              26601