First atroposelective Chan-Lam coupling for the synthesis of C-N linked biaryls.
Ishida, Moeka; Adachi, Rina; Kobayashi, Kazuki; Yamamoto, Yukiko; Kawahara, Chinatsu; Yamada, Tsuyoshi; Aoyama, Hiroshi; Kanomata, Kyohei; Akai, Shuji; Lam, Patrick Y. S.; Sajiki, Hironao; Ikawa, Takashi; Chemical communications (Cambridge, England) 60 (2024) 678–681; doi:10.1039/d3cc05447k

data_7132503
_publ_section_title
;
 First atroposelective Chan-Lam coupling for the synthesis of C-N linked
 biaryls.
;
_journal_issue                   6
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              678
_journal_page_last               681
_journal_paper_doi               10.1039/d3cc05447k
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C18 H13 Br N2 O'
_chemical_formula_sum            'C18 H13 Br N2 O'
_chemical_formula_weight         353.22
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2023-09-21 deposited with the CCDC.	2023-12-17 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   7.0262(11)
_cell_length_b                   9.2338(14)
_cell_length_c                   24.100(4)
_cell_measurement_reflns_used    4428
_cell_measurement_temperature    273
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.02
_cell_volume                     1563.6(4)
_computing_cell_refinement       DTREK
_computing_data_collection       DTREK
_computing_data_reduction        DTREK
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      273
_diffrn_detector_area_resol_mean 5.811
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0669
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            10418
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         3.020
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.639
_exptl_absorpt_correction_T_max  0.453
_exptl_absorpt_correction_T_min  0.184
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             712.00
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.50
_refine_diff_density_min         -0.59
_refine_ls_abs_structure_details
;
 Flack x determined using 1165 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3443
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0277
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/[\s^2^(Fo^2^)]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0539
_refine_ls_wR_factor_ref         0.0543
_reflns_Friedel_coverage         0.676
_reflns_Friedel_fraction_full    0.961
_reflns_Friedel_fraction_max     0.926
_reflns_number_gt                3099
_reflns_number_total             3443
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            d3cc05447k3.cif
_cod_data_source_block           C18H13BrN2O-1
_cod_depositor_comments          'Adding full bibliography for 7132503.cif.'
_cod_original_cell_volume        1563.5(4)
_cod_database_code               7132503
_shelx_res_checksum              3281
_shelx_hkl_checksum              34054