Divergent Ritter-type amination via photoredox catalytic four-component radical-polar crossover reactions
Guo, Sheng-Qiang; Yang, Hui-Qing; Wang, Ai-Lian; Jiang, Yu-Zhen; Xu, Guo-Qiang; Luo, Yong-Chun; Chen, Zhao-Xu; Xu, Peng-Fei; Green Chemistry 23 (2021) 9571–9576; doi:10.1039/D1GC03048E

data_7243893
_publ_section_title
;
 Divergent Ritter-type amination via photoredox catalytic four-component
 radical-polar crossover reactions
;
_journal_issue                   23
_journal_name_full               'Green Chemistry'
_journal_page_first              9571
_journal_page_last               9576
_journal_paper_doi               10.1039/D1GC03048E
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C22 H18 Cl F N4 O2 S'
_chemical_formula_sum            'C22 H19 Cl F N4 O2 S'
_chemical_formula_weight         457.92
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2020-06-12
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2021-03-27 deposited with the CCDC.	2021-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.637(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.17026(19)
_cell_length_b                   21.7971(5)
_cell_length_c                   13.6848(4)
_cell_measurement_reflns_used    3105
_cell_measurement_temperature    293.1(2)
_cell_measurement_theta_max      69.5310
_cell_measurement_theta_min      6.9120
_cell_volume                     2114.55(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.1(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     -9.00  16.00   1.00    1.00    --    0.00  57.00  30.00   25
  2  \w     30.00  68.00   1.00    1.00    --    0.00  57.00  90.00   38
  3  \w     25.00 121.00   1.00    1.00    --   54.00  19.00 -30.00   96
  4  \w     76.00 123.00   1.00    2.00    --  108.00 -38.00 -60.00   47
  5  \w    103.00 164.00   1.00    2.00    --  108.00  38.00-150.00   61
  6  \w     92.00 176.00   1.00    2.00    --  108.00  63.00-120.00   84
  7  \w    119.00 145.00   1.00    2.00    --  108.00 111.00   0.00   26
  8  \w     34.00 124.00   1.00    1.00    --   54.00  38.00-150.00   90
  9  \w     39.00  66.00   1.00    2.00    --  108.00 -38.00 -60.00   27
 10  \w     42.00 129.00   1.00    2.00    --  108.00 -77.00   0.00   87
 11  \w     38.00 124.00   1.00    2.00    --  108.00 -50.00  90.00   86
 12  \w     36.00  62.00   1.00    2.00    --  108.00-111.00 -30.00   26
 13  \w     31.00 111.00   1.00    1.00    --   54.00-125.00   0.00   80
 14  \w     53.00 116.00   1.00    2.00    --  108.00-111.00-180.00   63
 15  \w    -20.00  16.00   1.00    1.00    --    0.00  57.00-150.00   36
 16  \w     -1.00  25.00   1.00    1.00    --    0.00  57.00  90.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0605163000
_diffrn_orient_matrix_UB_12      -0.0373976000
_diffrn_orient_matrix_UB_13      0.0854728000
_diffrn_orient_matrix_UB_21      -0.2033764000
_diffrn_orient_matrix_UB_22      -0.0028331000
_diffrn_orient_matrix_UB_23      -0.0555167000
_diffrn_orient_matrix_UB_31      0.0474888000
_diffrn_orient_matrix_UB_32      -0.0598779000
_diffrn_orient_matrix_UB_33      -0.0507052000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7622
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.592
_diffrn_reflns_theta_max         66.592
_diffrn_reflns_theta_min         3.845
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.837
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68738
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_description       block
_exptl_crystal_F_000             948
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3737
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0545
_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^)+(0.0829P)^2^+0.9638P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1452
_refine_ls_wR_factor_ref         0.1552
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3148
_reflns_number_total             3737
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc03048e2.cif
_cod_data_source_block           guoshq_0605
_cod_depositor_comments
'Adding full bibliography for 7243893--7243896.cif.'
_cod_original_cell_volume        2114.56(10)
_cod_database_code               7243893
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C19(H19), C2(H2), C20(H20), C10(H10), C6(H6), C21(H21), C5(H5),
 C13(H13), C11(H11), C12(H12), C18(H18)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_shelx_res_checksum              958
_olex2_date_sample_data_collection 2020-06-05
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.122
_oxdiff_exptl_absorpt_empirical_full_min 0.545