Diasteroselective and Enantioselective Ir-Catalyzed Allylic Substitutions of 1-Substituted 1-Fluoro-1-(arenesulfonyl)methylene Derivatives.
Chen, Jiteng; Zhao, Xiaoming; Dan, Wenyan; The Journal of organic chemistry 82 (2017) 10693–10698; doi:10.1021/acs.joc.7b01782

data_4032862
_publ_section_title
;
 Diasteroselective and Enantioselective Ir-Catalyzed Allylic Substitutions
 of 1-Substituted 1-Fluoro-1-(arenesulfonyl)methylene Derivatives.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10693
_journal_page_last               10698
_journal_paper_doi               10.1021/acs.joc.7b01782
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H15 Br F N O3 S'
_chemical_formula_weight         412.27
_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'
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_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9810(6)
_cell_length_b                   9.1535(5)
_cell_length_c                   20.8614(14)
_cell_measurement_reflns_used    9149
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      25.97
_cell_measurement_theta_min      2.96
_cell_volume                     1714.97(19)
_computing_cell_refinement       'Bruker SAINT'
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_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
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_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-III CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            26653
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.668
_diffrn_reflns_theta_min         2.961
_exptl_absorpt_coefficient_mu    2.544
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_description       block
_exptl_crystal_F_000             832
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_exptl_crystal_size_min          0.150
_exptl_transmission_factor_max   0.7453
_exptl_transmission_factor_min   0.6345
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
; 
 Flack x determined using 1100 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.012(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3229
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0344
_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^)+(0.0474P)^2^+1.1612P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0878
_refine_ls_wR_factor_ref         0.0939
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                2838
_reflns_number_total             3229
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01782_si_003.cif
_cod_data_source_block           mo_170623c_a
_cod_depositor_comments
'Adding full bibliography for 4032862--4032863.cif.'
_cod_database_code               4032862
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.470
_shelx_estimated_absorpt_t_max   0.702
_shelx_res_checksum              89285
_shelx_hkl_checksum              33719