Pd-Catalyzed Umpolung Asymmetric Allylic Alkylation of Hydrazones to Vicinal Tertiary and Quaternary Chiral Carbon Centers
Huang, Shuai; Zhang, Gao-Peng; Jiang, Yang-Jie; Yu, Fei-Le; Ding, Chang-Hua; Hou, Xuelong; Chemical Communications  (2022) –; doi:10.1039/D1CC07074F

data_7129708
_publ_section_title
;
 Pd-Catalyzed Umpolung Asymmetric Allylic Alkylation of Hydrazones to
 Vicinal Tertiary and Quaternary Chiral Carbon Centers
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC07074F
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_sum            'C22 H24 Br N O'
_chemical_formula_weight         398.33
_space_group_crystal_system      hexagonal
_space_group_IT_number           169
_space_group_name_Hall           'P 61'
_space_group_name_H-M_alt        'P 61'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2020-03-24 deposited with the CCDC.	2022-02-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   12.7423(15)
_cell_length_b                   12.7423(15)
_cell_length_c                   22.890(4)
_cell_measurement_reflns_used    2018
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      34.333
_cell_measurement_theta_min      5.128
_cell_volume                     3218.6(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0730
_diffrn_reflns_av_unetI/netI     0.0800
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            17759
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_min         1.845
_exptl_absorpt_coefficient_mu    1.924
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1236
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_platon_squeeze_details
;
;
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
; 
 Flack x determined using 805 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.017(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3759
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1108
_refine_ls_R_factor_gt           0.0701
_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^)+(0.1129P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1840
_refine_ls_wR_factor_ref         0.2033
_reflns_Friedel_coverage         0.940
_reflns_Friedel_fraction_full    0.963
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                2194
_reflns_number_total             3759
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc07074f2.cif
_cod_data_source_block           cd16696
_cod_original_cell_volume        3218.7(9)
_cod_database_code               7129708
_shelx_estimated_absorpt_t_min   0.700
_shelx_estimated_absorpt_t_max   0.802
_shelxl_version_number           2013-4
_shelx_res_checksum              21606