Dual-Ligand-Enabled Ir(III)-Catalyzed Enantioselective C–H Amidation for the Synthesis of Chiral Sulfoxides
Liu, Wentan; Yang, Wu; Zhu, Jiefeng; Guo, Yonghong; Wang, Na; Ke, Jie; Yu, Peiyuan; He, Chuan; ACS Catalysis 10 (2020) 7207–7215; doi:10.1021/acscatal.0c02109

data_4517774
_publ_section_title
;
 Dual-Ligand-Enabled Ir(III)-Catalyzed Enantioselective C--H Amidation for
 the Synthesis of Chiral Sulfoxides
;
_journal_issue                   13
_journal_name_full               'ACS Catalysis'
_journal_page_first              7207
_journal_page_last               7215
_journal_paper_doi               10.1021/acscatal.0c02109
_journal_volume                  10
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H17 Br2 N O2 S'
_chemical_formula_sum            'C21 H17 Br2 N O2 S'
_chemical_formula_weight         507.24
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                87.720(8)
_cell_angle_beta                 86.471(8)
_cell_angle_gamma                89.947(7)
_cell_formula_units_Z            2
_cell_length_a                   5.2215(13)
_cell_length_b                   7.9597(19)
_cell_length_c                   23.385(6)
_cell_measurement_reflns_used    9839
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.67
_cell_volume                     969.3(4)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker CMOS area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0713
_diffrn_reflns_av_unetI/netI     0.0926
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            20397
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.548
_diffrn_reflns_theta_min         2.561
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.306
_exptl_absorpt_correction_T_max  0.0949
_exptl_absorpt_correction_T_min  0.0463
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1382 before and 0.0880 after correction. The Ratio of minimum to maximum transmission is 0.4879. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.738
_exptl_crystal_description       plate
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.04
_refine_diff_density_max         2.835
_refine_diff_density_min         -1.237
_refine_diff_density_rms         0.188
_refine_ls_abs_structure_details
;
 Flack x determined using 2972 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.040(18)
_refine_ls_extinction_coef       0.016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     488
_refine_ls_number_reflns         8754
_refine_ls_number_restraints     39
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1000
_refine_ls_R_factor_gt           0.0875
_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^)+(0.0944P)^2^+17.4523P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2155
_refine_ls_wR_factor_ref         0.2280
_reflns_Friedel_coverage         0.960
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.958
_reflns_number_gt                7778
_reflns_number_total             8754
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c02109_si_007.cif
_cod_data_source_block           cxy1309_0m
_cod_depositor_comments
;Adding full bibliography for 4517774--4517778.cif.

 Adding full bibliography for 4517774--4517778.cif.
;
_cod_database_code               4517774
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.847
_shelx_estimated_absorpt_t_min   0.265
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C4) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C41)
\\sim Ueq, Uanis(C36) \\sim Ueq, Uanis(C37) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C25(H25A,H25B), C26(H26A,H26B)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C42(H42), N3(H3A), C40(H40), C41(H41), C2(H2), C3(H3), C11(H11),
 C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C18(H18), C19(H19), C20(H20),
  C22(H22), C23(H23), C31(H31), C32(H32), C33(H33), C34(H34), C35(H35),
 C36(H36), C38(H38), C39(H39)
;
_olex2_submission_special_instructions 'No special instructions were received'