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_1559050
_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_absolute_configuration ad
_chemical_formula_sum            'C19 H17 N O2'
_chemical_formula_weight         291.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-10-23 deposited with the CCDC.	2020-09-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.2250(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.9647(3)
_cell_length_b                   9.7465(4)
_cell_length_c                   9.2350(3)
_cell_measurement_reflns_used    9961
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      53.96
_cell_measurement_theta_min      3.95
_cell_volume                     757.15(5)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_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  0.0306
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12804
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         53.959
_diffrn_reflns_theta_min         9.085
_exptl_absorpt_coefficient_mu    0.420
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.116
_refine_diff_density_min         -0.114
_refine_diff_density_rms         0.022
_refine_ls_abs_structure_details
;
 Flack x determined using 1229 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2691
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0261
_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^)+(0.0491P)^2^+0.0332P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0737
_reflns_Friedel_coverage         0.877
_reflns_Friedel_fraction_full    0.970
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                2666
_reflns_number_total             2691
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02828b2.cif
_cod_data_source_block           20191017ZH_LMF_2KL_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_absolute_configuration' value 'AD' was changed
to 'ad' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1559050
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.951
_shelx_estimated_absorpt_t_max   0.963
_shelx_res_checksum              95551