Enantioselective Formation of CF3-Bearing All-Carbon Quaternary Stereocenters via C–H Functionalization of Methanol: Iridium Catalyzed Allene Hydrohydroxymethylation
Holmes, Michael; Nguyen, Khoa D.; Schwartz, Leyah A.; Luong, Tom; Krische, Michael J.; Journal of the American Chemical Society  (2017) –; doi:10.1021/jacs.7b04374

data_4126211
_publ_section_title
;
 Enantioselective Formation of CF3-Bearing All-Carbon Quaternary
 Stereocenters via C--H Functionalization of Methanol: Iridium Catalyzed
 Allene Hydrohydroxymethylation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b04374
_journal_year                    2017
_chemical_formula_sum            'C18 H13 Br Cl F3 O2'
_chemical_formula_weight         433.64
_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-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 116.91(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.375(10)
_cell_length_b                   7.357(6)
_cell_length_c                   11.576(9)
_cell_measurement_temperature    296(2)
_cell_volume                     863.9(13)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.972
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1043
_diffrn_reflns_av_unetI/netI     0.1434
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8168
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.558
_diffrn_reflns_theta_min         1.973
_exptl_absorpt_coefficient_mu    2.573
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_F_000             432
_refine_diff_density_max         0.971
_refine_diff_density_min         -0.756
_refine_diff_density_rms         0.106
_refine_ls_abs_structure_details
;
 Flack x determined using 623 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.025(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3055
_refine_ls_number_restraints     151
_refine_ls_restrained_S_all      0.971
_refine_ls_R_factor_all          0.1164
_refine_ls_R_factor_gt           0.0602
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0585P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1560
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_full    0.939
_reflns_Friedel_fraction_max     0.908
_reflns_number_gt                1863
_reflns_number_total             3055
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b04374_si_002.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        863.8(13)
_cod_database_code               4126211
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              96153
_shelx_hkl_checksum              38365