Asymmetric allylic substitution–isomerization to axially chiral enamides via hydrogen-bonding assisted central-to-axial chirality transfer
Sun, Chao; Qi, Xiaotian; Min, Xiao-Long; Bai, Xue-Dan; Liu, Peng; He, Ying; Chemical Science  (2020) –; doi:10.1039/D0SC02828B

data_1559049
_publ_section_title
;
 Asymmetric allylic substitution--isomerization to axially chiral enamides
 via hydrogen-bonding assisted central-to-axial chirality transfer
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02828B
_journal_year                    2020
_chemical_formula_sum            'C18 H14 Cl N O'
_chemical_formula_weight         295.75
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-07-18 deposited with the CCDC.	2020-09-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1789(9)
_cell_length_b                   8.6698(11)
_cell_length_c                   24.751(3)
_cell_measurement_reflns_used    9977
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      59.88
_cell_measurement_theta_min      3.11
_cell_volume                     1540.5(3)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0838
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            20404
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        52.998
_diffrn_reflns_theta_max         52.998
_diffrn_reflns_theta_min         3.107
_exptl_absorpt_coefficient_mu    1.429
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 532 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.18(2)
_refine_ls_extinction_coef       0.029(3)
_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   1.169
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2719
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.169
_refine_ls_R_factor_all          0.1141
_refine_ls_R_factor_gt           0.0874
_refine_ls_shift/su_max          0.027
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+2.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1737
_refine_ls_wR_factor_ref         0.1863
_reflns_Friedel_coverage         0.703
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                1853
_reflns_number_total             2719
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02828b2.cif
_cod_data_source_block           20190717HU_LWF_0m_a
_cod_database_code               1559049
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.793
_shelx_estimated_absorpt_t_max   0.859
_shelx_res_checksum              54568