syn-Selective Construction of Fused Heterocycles by Catalytic Reductive Tandem Functionalization of N-Heteroarenes
Yang, Jian; Zhao, He; Tan, Zhenda; Cao, Liang; Jiang, Huanfeng; Ci, Chenggang; Dixneuf, Pierre H.; Zhang, Min; ACS Catalysis  (2021) 9271–9278; doi:10.1021/acscatal.1c01328

data_4518886
_publ_section_title
;
 syn-Selective Construction of Fused Heterocycles by Catalytic Reductive
 Tandem Functionalization of N-Heteroarenes
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              9271
_journal_page_last               9278
_journal_paper_doi               10.1021/acscatal.1c01328
_journal_year                    2021
_chemical_formula_moiety         'C28 H25 N O2'
_chemical_formula_sum            'C28 H25 N O2'
_chemical_formula_weight         407.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 95.763(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.627(3)
_cell_length_b                   6.7071(12)
_cell_length_c                   17.181(4)
_cell_measurement_reflns_used    4972
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.383
_cell_measurement_theta_min      3.405
_cell_volume                     2135.6(7)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.845
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_unetI/netI     0.1068
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.845
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12245
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.383
_diffrn_reflns_theta_min         3.405
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.594
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4972
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1850
_refine_ls_R_factor_gt           0.0730
_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^)+(0.0745P)^2^+0.1719P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1553
_refine_ls_wR_factor_ref         0.2036
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2172
_reflns_number_total             4972
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c01328_si_002.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4518886
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              66079
_shelx_hkl_checksum              10775