Rhodium-Catalyzed Atroposelective C-H Arylation: Efficient Synthesis of Axially Chiral Heterobiaryls.
Wang, Qiang; Cai, Zhong-Jian; Liu, Chen-Xu; Gu, Qing; You, Shu-Li; Journal of the American Chemical Society 141 (2019) 9504–9510; doi:10.1021/jacs.9b03862

data_4127438
_publ_section_title
;
 Rhodium-Catalyzed Atroposelective C-H Arylation: Efficient Synthesis of
 Axially Chiral Heterobiaryls.
;
_journal_issue                   24
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9504
_journal_page_last               9510
_journal_paper_doi               10.1021/jacs.9b03862
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C27 H21 N O'
_chemical_formula_sum            'C27 H21 N O'
_chemical_formula_weight         375.45
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4161(2)
_cell_length_b                   14.1640(2)
_cell_length_c                   15.0633(3)
_cell_measurement_reflns_used    9989
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.932
_cell_measurement_theta_min      3.728
_cell_volume                     2008.99(7)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      169.99
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12950
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.907
_diffrn_reflns_theta_min         3.727
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.374
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5201
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1319 before and 0.0619 after correction. The Ratio of minimum to maximum transmission is 0.6927. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1529 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3783
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0475P)^2^+0.1712P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0861
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                3663
_reflns_number_total             3783
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b03862_si_002.cif
_cod_data_source_block           mj19072_0m
_cod_database_code               4127438
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.946
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C21(H21), C23(H23), C25(H25)
2.b Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              92765
_shelx_hkl_checksum              78266
_olex2_submission_special_instructions 'No special instructions were received'