Rhodium-Catalyzed Regio-, Diastereo-, and Enantioselective Three-Component Carboamination of Dienes via C‒H Activation
Mi, Ruijie; Zhang, Xuepeng; Wang, Jinlei; Chen, Haohua; Lan, Yu; Wang, Fen; Li, Xingwei; ACS Catalysis  (2021) 6692–6697; doi:10.1021/acscatal.1c01615

data_4518738
_publ_section_title
;
 Rhodium-Catalyzed Regio-, Diastereo-, and Enantioselective
 Three-Component Carboamination of Dienes via C--H Activation
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              6692
_journal_page_last               6697
_journal_paper_doi               10.1021/acscatal.1c01615
_journal_year                    2021
_chemical_formula_moiety         'C24 H27 I N2 O2, C H2 Cl2'
_chemical_formula_sum            'C25 H29 Cl2 I N2 O2'
_chemical_formula_weight         587.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-02-02
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_cell_angle_alpha                90
_cell_angle_beta                 115.579(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.666(3)
_cell_length_b                   10.1915(18)
_cell_length_c                   16.848(3)
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    226.0
_cell_measurement_theta_max      68.194
_cell_measurement_theta_min      2.939
_cell_volume                     2581.2(8)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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      226.0
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25932
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.681
_diffrn_reflns_theta_min         2.939
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    11.840
_exptl_absorpt_correction_T_max  0.1665
_exptl_absorpt_correction_T_min  0.0429
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1373 before and 0.0893 after correction.
The Ratio of minimum to maximum transmission is 0.2577.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         2.815
_refine_diff_density_min         -0.665
_refine_diff_density_rms         0.177
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4715
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0762
_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^)+(0.1485P)^2^+5.7333P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2174
_refine_ls_wR_factor_ref         0.2273
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4042
_reflns_number_total             4715
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c01615_si_001.cif
_cod_data_source_block           s
_cod_database_code               4518738
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.125
_shelx_estimated_absorpt_t_min   0.066
_olex2_refinement_description
;
1. 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
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C22(H22A,H22B), C15(H15A,H15B), C9(H9A,H9B), C23(H23A,H23B),
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C8(H8), C14(H14), C20(H20), C25(H25), C13(H13), C7(H7), C2(H2A),
 C19(H19), C5(H5)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C11(H11A,H11B,H11C)
;
_shelx_res_checksum              8729
_shelx_hkl_checksum              31344
_olex2_submission_special_instructions 'No special instructions were received'