Palladium-catalyzed diastereoselective cross-coupling of two aryl halides <i>via</i> C-H activation: synthesis of chiral eight-membered nitrogen heterocycles.
Cheng, Cang; Zuo, Xiang; Tu, Dongdong; Wan, Bin; Zhang, Yanghui; Chemical communications (Cambridge, England) 57 (2021) 2939–2942; doi:10.1039/d1cc00398d

data_7127936
_publ_section_title
;
 Palladium-catalyzed diastereoselective cross-coupling of two aryl halides
 <i>via</i> C-H activation: synthesis of chiral eight-membered nitrogen
 heterocycles.
;
_journal_issue                   23
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2939
_journal_page_last               2942
_journal_paper_doi               10.1039/d1cc00398d
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration rm
_chemical_formula_sum            'C20 H17 N'
_chemical_formula_weight         271.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc26mkdt
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2020-11-16 deposited with the CCDC.	2021-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.6600(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.9144(8)
_cell_length_b                   7.7719(4)
_cell_length_c                   22.6944(10)
_cell_measurement_reflns_used    9893
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.78
_cell_measurement_theta_min      4.09
_cell_volume                     2842.7(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-III CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            21990
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.496
_diffrn_reflns_theta_min         4.088
_exptl_absorpt_coefficient_mu    0.558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_transmission_factor_max   0.7542
_exptl_transmission_factor_min   0.6810
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
; 
 Flack x determined using 2509 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.4(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         5677
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0383
_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^)+(0.0643P)^2^+1.6409P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1009
_reflns_Friedel_coverage         0.826
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                5639
_reflns_number_total             5677
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc00398d2.cif
_cod_data_source_block           cu_200727c_a
_cod_depositor_comments
'Adding full bibliography for 7127936--7127937.cif.'
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               7127936
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_min   0.851
_shelx_estimated_absorpt_t_max   0.936
_shelx_res_checksum              95880
_shelx_hkl_checksum              46816