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_4514326
_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         'C17 H13 Br F2 O2'
_chemical_formula_sum            'C17 H13 Br F2 O2'
_chemical_formula_weight         367.18
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 92.604(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.1462(18)
_cell_length_b                   7.5224(7)
_cell_length_c                   22.412(2)
_cell_measurement_reflns_used    10705
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      25,3
_cell_measurement_theta_min      1.0
_cell_volume                     3056.1(5)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor)'
_computing_data_collection       'Collect (Nonius BV, 2000)'
_computing_data_reduction        'HKL Denzo, Scalepack (Otwinowski & Minor)'
_computing_molecular_graphics    'Shelxtl v6.1 (Sheldrick, 2008)'
_computing_publication_material  'Shelxtl v6.1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Shelxtl v6.1 (Sheldrick, 2008)'
_diffrn_ambient_temperature      190(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD phi and omegs scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_av_unetI/netI     0.0845
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            53974
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.359
_diffrn_reflns_theta_min         2.386
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.715
_exptl_absorpt_correction_T_max  0.9501
_exptl_absorpt_correction_T_min  0.3831
_exptl_absorpt_correction_type   multi-scan
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_exptl_crystal_density_diffrn    1.596
_exptl_crystal_description       plate
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details
;
 Flack x determined using 2601 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(5)
_refine_ls_extinction_coef       0.0216(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     794
_refine_ls_number_reflns         11122
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0394P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0917
_reflns_Friedel_coverage         0.841
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                7497
_reflns_number_total             11122
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs7b03786_si_005.cif
_cod_data_source_block           ngu153
_cod_depositor_comments
'Adding full bibliography for 4514324--4514328.cif.'
_cod_database_code               4514326
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.550
_shelx_estimated_absorpt_t_max   0.923
_shelx_res_checksum              68578
_shelx_hkl_checksum              94668