Ir(III)-Catalyzed Stereoselective Haloamidation of Alkynes Enabled by Ligand Participation.
Hong, Seung Youn; Son, Junsoo; Kim, Dongwook; Chang, Sukbok; Journal of the American Chemical Society 140 (2018) 12359–12363; doi:10.1021/jacs.8b08134

data_4133044
_publ_section_title
;
 Ir(III)-Catalyzed Stereoselective Haloamidation of Alkynes Enabled by
 Ligand Participation.
;
_journal_issue                   39
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12359
_journal_page_last               12363
_journal_paper_doi               10.1021/jacs.8b08134
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration syn
_chemical_formula_sum            'C28 H28 Cl N O2'
_chemical_formula_weight         445.96
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 101.13(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   37.321(7)
_cell_length_b                   7.4490(15)
_cell_length_c                   16.822(3)
_cell_measurement_reflns_used    36474
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.941
_cell_measurement_theta_min      0.384
_cell_volume                     4588.6(16)
_computing_cell_refinement       'HKL3000sm (Otwinowski & Minor, 1997)'
_computing_data_collection       'PAL BL2D-SMDC Program (Shin et. al, 2016)'
_computing_data_reduction        'HKL3000sm (Otwinowski & Minor, 1997)'
_computing_structure_refinement  SHELXL
_computing_structure_solution    SHELXS
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.845
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.670
_diffrn_reflns_av_R_equivalents  0.0864
_diffrn_reflns_av_unetI/netI     0.0792
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.845
_diffrn_reflns_limit_h_max       60
_diffrn_reflns_limit_h_min       -60
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            25545
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.788
_diffrn_reflns_theta_full        23.703
_diffrn_reflns_theta_max         33.524
_diffrn_reflns_theta_min         1.407
_diffrn_source                   'PLSII 2D bending magnet'
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.908
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       needle
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.123
_exptl_crystal_size_mid          0.018
_exptl_crystal_size_min          0.015
_refine_diff_density_max         1.464
_refine_diff_density_min         -1.231
_refine_diff_density_rms         0.122
_refine_ls_abs_structure_details
;
 Flack x determined using 5485 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     581
_refine_ls_number_reflns         17009
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0726
_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^)+(0.1317P)^2^+1.6286P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2002
_refine_ls_wR_factor_ref         0.2080
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    0.920
_reflns_Friedel_fraction_max     0.725
_reflns_number_gt                15074
_reflns_number_total             17009
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b08134_si_005.cif
_cod_data_source_block           P053_005
_cod_original_cell_volume        4588.6(17)
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4133044
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.980
_shelx_estimated_absorpt_t_max   0.998
_shelx_res_checksum              22125
_shelx_hkl_checksum              88378