The Role of Trichloroacetimidate To Enable Iridium-Catalyzed Regio- and Enantioselective Allylic Fluorination: A Combined Experimental and Computational Study.
Sorlin, Alexandre M.; Mixdorf, Jason C.; Rotella, Madeline E.; Martin, Robert T.; Gutierrez, Osvaldo; Nguyen, Hien M.; Journal of the American Chemical Society 141 (2019) 14843–14852; doi:10.1021/jacs.9b07575

data_4127618
_publ_section_title
;
 The Role of Trichloroacetimidate To Enable Iridium-Catalyzed Regio- and
 Enantioselective Allylic Fluorination: A Combined Experimental and
 Computational Study.
;
_journal_issue                   37
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14843
_journal_page_last               14852
_journal_paper_doi               10.1021/jacs.9b07575
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C21 H23 Cl4 F Ir N O3'
_chemical_formula_sum            'C21 H23 Cl4 F Ir N O3'
_chemical_formula_weight         690.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.266(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2586(7)
_cell_length_b                   18.0776(11)
_cell_length_c                   12.3309(9)
_cell_measurement_reflns_used    9630
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.26
_cell_measurement_theta_min      2.62
_cell_volume                     2242.7(3)
_computing_cell_refinement       'SAINT V8.30C (?, 2016)'
_computing_data_reduction        'SAINT V8.30C (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.1
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            134037
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.569
_diffrn_reflns_theta_min         2.253
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.463
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6654
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0793 before and 0.0556 after correction. The Ratio of minimum to maximum transmission is 0.8918. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            'clear yellowish'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_density_diffrn    2.045
_exptl_crystal_description       cube
_exptl_crystal_F_000             1336
_exptl_crystal_size_max          0.506
_exptl_crystal_size_mid          0.374
_exptl_crystal_size_min          0.349
_refine_diff_density_max         1.123
_refine_diff_density_min         -0.828
_refine_diff_density_rms         0.147
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         6863
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0235
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0154P)^2^+1.5877P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0387
_refine_ls_wR_factor_ref         0.0409
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5717
_reflns_number_total             6863
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b07575_si_002.cif
_cod_data_source_block           as0709_0m_2
_cod_database_code               4127618
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.211
_shelx_estimated_absorpt_t_min   0.138
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C5(H5), C2(H2), C10(H10), C1(H1A), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C4(H4A,H4B), C7(H7A,H7B), C3(H3A,H3B), C12(H12A,H12B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C16(H16), C15(H15), C18(H18)
;
_shelx_res_checksum              57312
_shelx_hkl_checksum              57374
_olex2_submission_special_instructions 'No special instructions were received'