Cp*RhIII/Chiral Disulfonate/CuOAc Catalyst System for the Enantioselective Intramolecular Oxyamination of Alkenes
Hirose, Jumpei; Wakikawa, Takumi; Satake, Shun; Kojima, Masahiro; Hatano, Manabu; Ishihara, Kazuaki; Yoshino, Tatsuhiko; Matsunaga, Shigeki; ACS Catalysis 11 (2021) 15187–15193; doi:10.1021/acscatal.1c04699

data_4519251
_publ_section_title
;
 Cp*RhIII/Chiral Disulfonate/CuOAc Catalyst System for the
 Enantioselective Intramolecular Oxyamination of Alkenes
;
_journal_issue                   24
_journal_name_full               'ACS Catalysis'
_journal_page_first              15187
_journal_page_last               15193
_journal_paper_doi               10.1021/acscatal.1c04699
_journal_volume                  11
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H31 N O4 S'
_chemical_formula_sum            'C28 H31 N O4 S'
_chemical_formula_weight         477.60
_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             2021-01-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_cell_angle_alpha                85.163(4)
_cell_angle_beta                 69.406(3)
_cell_angle_gamma                65.577(3)
_cell_formula_units_Z            2
_cell_length_a                   11.2477(7)
_cell_length_b                   11.2911(7)
_cell_length_c                   11.5245(7)
_cell_measurement_reflns_used    16010
_cell_measurement_temperature    233(2)
_cell_measurement_theta_max      68.21
_cell_measurement_theta_min      3.57
_cell_volume                     1244.26(14)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      233(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14241
_diffrn_reflns_point_group_measured_fraction_full 0.825
_diffrn_reflns_point_group_measured_fraction_max 0.823
_diffrn_reflns_theta_full        67.680
_diffrn_reflns_theta_max         68.144
_diffrn_reflns_theta_min         4.108
_diffrn_source_current           40.0
_diffrn_source_power             1.6
_diffrn_source_voltage           40.0
_exptl_absorpt_coefficient_mu    1.430
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.570
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.310
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.075(16)
_refine_ls_extinction_coef       0.0065(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     619
_refine_ls_number_reflns         7491
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0377
_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^)+(0.0758P)^2^+0.0137P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1062
_reflns_Friedel_coverage         0.679
_reflns_Friedel_fraction_full    0.669
_reflns_Friedel_fraction_max     0.666
_reflns_number_gt                7080
_reflns_number_total             7491
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c04699_si_003.cif
_cod_data_source_block           product
_cod_database_code               4519251
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.925(16)
 0.075(16)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C00J(H00A,H00B), C00P(H00E,H00H), C00Y(H00J,H00K), C010(H01R,H01S), C012(H01T,
 H01U), C014(H01A,H01B), C015(H01V,H01W), C017(H01X,H01Y), C019(H01C,H01D),
 C01A(H01Z,H), C01L(H01I,H01K), C01S(H5,HC)
3.b Aromatic/amide H refined with riding coordinates:
 N008(H008), C00C(H00C), C00D(H00D), N00F(H00F), C00G(H00G), C00I(H00I),
 C00O(H00O), C00R(H00R), C00S(H00S), C00W(H00W), C00X(H00X), C00Z(H00Z),
 C011(H011), C018(H018), C01B(H01), C01C(H1), C01D(H01E), C01E(H01F),
 C01F(H01G), C01H(H01H), C01J(H01J), C01M(H2), C01O(H3), C01T(H6), C01U(H7),
 C01V(H8)
3.c Idealised Me refined as rotating group:
 C01N(H01L,H01M,H01N), C01P(H4,HA,HB), C01Q(H01O,H01P,H01Q), C01W(H9,HD,HE)
;
_shelx_res_checksum              345
_shelx_hkl_checksum              77014
_olex2_submission_special_instructions 'No special instructions were received'