Pyrimidopteridine-Catalyzed Hydroamination of Stilbenes with Primary Amines: A Dual Photoredox and Hydrogen Atom Transfer Catalyst
Taeufer, Tobias; Hauptmann, Richy; El-Hage, Firas; Mayer, Thea S.; Jiao, Haijun; Rabeah, Jabor; Pospech, Jola; ACS Catalysis 11 (2021) 4862–4869; doi:10.1021/acscatal.0c05540

data_4518678
_publ_section_title
;
 Pyrimidopteridine-Catalyzed Hydroamination of Stilbenes with Primary
 Amines: A Dual Photoredox and Hydrogen Atom Transfer Catalyst
;
_journal_issue                   8
_journal_name_full               'ACS Catalysis'
_journal_page_first              4862
_journal_page_last               4869
_journal_paper_doi               10.1021/acscatal.0c05540
_journal_volume                  11
_journal_year                    2021
_chemical_formula_sum            'C22 H23 Cl F N'
_chemical_formula_weight         355.86
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 115.7240(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5798(5)
_cell_length_b                   9.6574(3)
_cell_length_c                   15.0886(5)
_cell_measurement_reflns_used    9880
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.47
_cell_measurement_theta_min      2.58
_cell_volume                     1913.97(11)
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        SAINT
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0223
_diffrn_reflns_av_unetI/netI     0.0113
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            45349
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_min         1.622
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       prism
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.404
_exptl_crystal_size_mid          0.257
_exptl_crystal_size_min          0.116
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4625
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0342
_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^)+(0.0427P)^2^+0.7339P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0932
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4080
_reflns_number_total             4625
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c05540_si_002.cif
_cod_data_source_block           AX1709
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4518678
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              32303
_shelx_hkl_checksum              25194