Enantioselective iridium catalyzed α-alkylation of azlactones by a tandem asymmetric allylic alkylation/aza-Cope rearrangement
Bai, Xue-Dan; Zhang, Qing-Feng; He, Ying; Chemical Communications  (2019) –; doi:10.1039/C9CC01450K

data_7123309
_publ_section_title
;
 Enantioselective iridium catalyzed \a-alkylation of azlactones by a
 tandem asymmetric allylic alkylation/aza-Cope rearrangement
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC01450K
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C24 H18 Cl N O2'
_chemical_formula_weight         387.84
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2018-12-24 deposited with the CCDC.    2019-04-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0263(5)
_cell_length_b                   16.9680(14)
_cell_length_c                   18.8850(16)
_cell_measurement_reflns_used    5712
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      68.36
_cell_measurement_theta_min      3.50
_cell_volume                     1931.1(3)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_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  0.0498
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10368
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        65.486
_diffrn_reflns_theta_max         65.485
_diffrn_reflns_theta_min         3.502
_exptl_absorpt_coefficient_mu    1.904
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details
;
 Flack x determined using 1145 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.031(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3213
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0475
_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^)+(0.0836P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1205
_reflns_Friedel_coverage         0.665
_reflns_Friedel_fraction_full    0.930
_reflns_Friedel_fraction_max     0.930
_reflns_number_gt                3040
_reflns_number_total             3213
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc01450k2.cif
_cod_data_source_block           cu_20181219LMF_0m_a
_cod_database_code               7123309
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.679
_shelx_estimated_absorpt_t_max   0.750
_shelx_res_checksum              92315
_shelx_hkl_checksum              53588