A lutidine-promoted photoredox catalytic atom-transfer radical cyclization reaction for the synthesis of 4-bromo-3,3-dialkyl-octahydro-indol-2-ones.
Zhao, Quan-Sheng; Xu, Guo-Qiang; Xu, Ji-Tao; Wang, Zhu-Yin; Xu, Peng-Fei; Chemical communications (Cambridge, England) 56 (2020) 2206–2209; doi:10.1039/c9cc09876c

data_7125827
_publ_section_title
;
 A lutidine-promoted photoredox catalytic atom-transfer radical
 cyclization reaction for the synthesis of
 4-bromo-3,3-dialkyl-octahydro-indol-2-ones.
;
_journal_issue                   14
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2206
_journal_page_last               2209
_journal_paper_doi               10.1039/c9cc09876c
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C24 H26 Cl N O2'
_chemical_formula_sum            'C24 H26 Cl N O2'
_chemical_formula_weight         395.91
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-06-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-03 deposited with the CCDC.	2020-01-16 downloaded from the CCDC.
;
_cell_angle_alpha                90.640(4)
_cell_angle_beta                 99.884(4)
_cell_angle_gamma                116.102(5)
_cell_formula_units_Z            2
_cell_length_a                   8.7322(5)
_cell_length_b                   9.3453(4)
_cell_length_c                   13.9189(7)
_cell_measurement_reflns_used    3588
_cell_measurement_temperature    291.96(10)
_cell_measurement_theta_max      69.9660
_cell_measurement_theta_min      8.2340
_cell_volume                     1000.03(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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.96(10)
_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    -13.00 124.00   1.00    1.00    --   54.00   0.00   0.00  137
  2  \w     96.00 178.00   1.00    1.00    --  108.00  25.00 -60.00   82
  3  \w    133.00 175.00   1.00    1.00    --  108.00  50.00   0.00   42
  4  \w     94.00 124.00   1.00    1.00    --  108.00 -50.00  90.00   30
  5  \w     78.00 137.00   1.00    1.00    --  108.00 -91.00  90.00   59
  6  \w     75.00 111.00   1.00    1.00    --  108.00-111.00  60.00   36
  7  \w     76.00 104.00   1.00    1.00    --  108.00-111.00 -30.00   28
  8  \w     52.00  88.00   1.00    1.00    --   54.00-125.00-120.00   36
  9  \w     39.00  65.00   1.00    1.00    --  108.00-111.00 -30.00   26
 10  \w     36.00  81.00   1.00    1.00    --  108.00-111.00  30.00   45
 11  \w     42.00 127.00   1.00    1.00    --  108.00 -63.00   0.00   85
 12  \w     63.00 126.00   1.00    1.00    --  108.00 -25.00-120.00   63
 13  \w     80.00 114.00   1.00    1.00    --  108.00-111.00-150.00   34
 14  \w     40.00 126.00   1.00    1.00    --  108.00 -63.00-150.00   86
 15  \w     40.00  74.00   1.00    1.00    --  108.00 -25.00-180.00   34
 16  \w     28.00 124.00   1.00    1.00    --   54.00  77.00-180.00   96
 17  \w     59.00  97.00   1.00    1.00    --  108.00 178.00 -90.00   38
 18  \w     29.00  64.00   1.00    1.00    --    0.00  77.00  60.00   35
 19  \w    -30.00  17.00   1.00    1.00    --    0.00  77.00  60.00   47
 20  \w     39.00  90.00   1.00    1.00    --  108.00 -50.00  90.00   51
 21  \w     36.00 135.00   1.00    1.00    --  108.00 -25.00 -30.00   99
 22  \w     24.00  55.00   1.00    1.00    --   54.00-125.00  90.00   31
 23  \w     23.00 108.00   1.00    1.00    --   54.00-125.00 150.00   85
 24  \w     23.00  61.00   1.00    1.00    --   54.00-125.00  30.00   38
 25  \w     -7.00  51.00   1.00    1.00    --   54.00 -57.00-120.00   58
 26  \w    -72.00 -26.00   1.00    1.00    --    0.00 -38.00 -60.00   46
;
_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      -0.1643976000
_diffrn_orient_matrix_UB_12      -0.0406700000
_diffrn_orient_matrix_UB_13      0.0425703000
_diffrn_orient_matrix_UB_21      -0.1135950000
_diffrn_orient_matrix_UB_22      -0.1059778000
_diffrn_orient_matrix_UB_23      -0.0951272000
_diffrn_orient_matrix_UB_31      0.0147579000
_diffrn_orient_matrix_UB_32      -0.1453930000
_diffrn_orient_matrix_UB_33      0.0433964000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6168
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.595
_diffrn_reflns_theta_max         66.595
_diffrn_reflns_theta_min         5.296
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.839
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24759
_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    1.315
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3532
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0473
_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^)+(0.0719P)^2^+0.2774P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1248
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3266
_reflns_number_total             3532
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc09876c3.cif
_cod_data_source_block           zhaoqsh_0603
_cod_depositor_comments
'Adding full bibliography for 7125826--7125827.cif.'
_cod_original_cell_volume        1000.04(9)
_cod_database_code               7125827
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.83
_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:
 C4(H4), C7(H7), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C17(H17A,H17B), C19(H19A,H19B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C9(H9), C11(H11), C14(H14), C23(H23), C24(H24), C25(H25),
 C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_shelx_res_checksum              85808
_olex2_date_sample_data_collection 2019-06-03
_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 3.642
_oxdiff_exptl_absorpt_empirical_full_min 0.640