Enantioselective Atropisomeric Anilides Synthesis via Cu-Catalyzed Intramolecular Adjacent C–N Coupling
Fan, Xiaozhong; Zhang, Xue; Li, Chunyu; Gu, Zhenhua; ACS Catalysis 9 (2019) 2286–; doi:10.1021/acscatal.8b04789

data_4514861
_publ_section_title
;
 Enantioselective Atropisomeric Anilides Synthesis via Cu-Catalyzed
 Intramolecular Adjacent C--N Coupling
;
_journal_issue                   3
_journal_name_full               'ACS Catalysis'
_journal_page_first              2286
_journal_paper_doi               10.1021/acscatal.8b04789
_journal_volume                  9
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H14 Cl N O'
_chemical_formula_sum            'C20 H14 Cl N O'
_chemical_formula_weight         319.77
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                89.235(3)
_cell_angle_beta                 77.991(2)
_cell_angle_gamma                89.031(2)
_cell_formula_units_Z            4
_cell_length_a                   8.6566(5)
_cell_length_b                   11.3426(5)
_cell_length_c                   16.5840(9)
_cell_measurement_reflns_used    4352
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.35
_cell_measurement_theta_min      2.98
_cell_volume                     1592.41(14)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            51413
_diffrn_reflns_point_group_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.397
_diffrn_reflns_theta_min         2.936
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.646
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 4308 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.016(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     898
_refine_ls_number_reflns         12184
_refine_ls_number_restraints     557
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0445
_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^)+(0.0165P)^2^+1.3430P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0932
_reflns_Friedel_coverage         0.875
_reflns_Friedel_fraction_full    0.884
_reflns_Friedel_fraction_max     0.872
_reflns_number_gt                10402
_reflns_number_total             12184
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b04789_si_002.cif
_cod_data_source_block           1
_cod_database_code               4514861
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.920
_shelx_estimated_absorpt_t_max   0.960
_shelx_res_checksum              9697
_shelx_hkl_checksum              67819