Nucleophilic Dearomatization of N-Heteroaromatics Enabled by Lewis Acids and Copper Catalysis.
Yan, Xingchen; Ge, Luo; Castiñeira Reis, Marta; Harutyunyan, Syuzanna R.; Journal of the American Chemical Society 142 (2020) 20247–20256; doi:10.1021/jacs.0c09974

data_4135350
_publ_section_title
;
 Nucleophilic Dearomatization of N-Heteroaromatics Enabled by Lewis Acids
 and Copper Catalysis.
;
_journal_issue                   47
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              20247
_journal_page_last               20256
_journal_paper_doi               10.1021/jacs.0c09974
_journal_volume                  142
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C11 H14 Br N'
_chemical_formula_weight         240.14
_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   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 94.8830(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.8938(3)
_cell_length_b                   5.9958(2)
_cell_length_c                   9.5190(3)
_cell_measurement_reflns_used    7072
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.12
_cell_measurement_theta_min      4.66
_cell_volume                     505.76(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6932
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        65.118
_diffrn_reflns_theta_max         65.118
_diffrn_reflns_theta_min         4.662
_exptl_absorpt_coefficient_mu    5.129
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_description       platelet
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_transmission_factor_max   0.7526
_exptl_transmission_factor_min   0.4121
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Flack x determined using 732 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.040(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         1702
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0176
_refine_ls_R_factor_gt           0.0174
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0238P)^2^+0.0615P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0420
_refine_ls_wR_factor_ref         0.0421
_reflns_Friedel_coverage         0.782
_reflns_Friedel_fraction_full    0.966
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                1689
_reflns_number_total             1702
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c09974_si_001.cif
_cod_data_source_block           cu_hv022_0m_b
_cod_depositor_comments          'Adding full bibliography for 4135350.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4135350
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.222
_shelx_estimated_absorpt_t_max   0.861
_shelx_res_checksum              36810
_shelx_hkl_checksum              56070