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_7125826
_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 Br N O2'
_chemical_formula_sum            'C24 H26 Br N O2'
_chemical_formula_weight         440.37
_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   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-04-03
_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                90.728(4)
_cell_angle_beta                 101.126(4)
_cell_angle_gamma                116.691(5)
_cell_formula_units_Z            2
_cell_length_a                   8.8862(4)
_cell_length_b                   9.2731(5)
_cell_length_c                   14.1317(6)
_cell_measurement_reflns_used    3950
_cell_measurement_temperature    291.19(19)
_cell_measurement_theta_max      69.6840
_cell_measurement_theta_min      6.2530
_cell_volume                     1014.27(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.19(19)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  111.00  146.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000  120.0000 35

  2 omega   63.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 53

  3 omega   57.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 58

  4 omega   51.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000  -90.0000 60

  5 omega   52.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -60.0000 38

  6 omega   49.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -73.0000    3.0000 27

  7 omega   43.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 62

  8 omega   55.00   95.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000  120.0000 40

  9 omega   49.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  120.0000 35

 10 omega   38.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   60.0000 65

 11 omega   41.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 44

 12 omega  -11.00   79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000  150.0000 90

 13 omega   33.00  125.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000   90.0000 92

 14 omega  101.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   73.0000  132.0000 76

 15 omega  106.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   90.0000 72

 16 omega   97.00  124.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  -60.0000 27

 17 omega   89.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000 -150.0000 87

 18 omega   84.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000  -90.0000 93

 19 omega   88.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000 -180.0000 88

 20 omega   46.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000 -150.0000 26

 21 omega   42.00  123.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -60.0000 81

 22 omega   47.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  -60.0000 27

 23 omega   46.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -150.0000 45

 24 omega   24.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000 -180.0000 41

 25 omega  -10.00   32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -73.0000    3.0000 42

 26 omega  -26.00   23.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000 -150.0000 49

 27 omega  -60.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   60.0000 49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1143186000
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_diffrn_orient_matrix_UB_21      -0.1511235000
_diffrn_orient_matrix_UB_22      -0.0257015000
_diffrn_orient_matrix_UB_23      -0.0845321000
_diffrn_orient_matrix_UB_31      -0.0608668000
_diffrn_orient_matrix_UB_32      0.0882770000
_diffrn_orient_matrix_UB_33      0.0648793000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6463
_diffrn_reflns_point_group_measured_fraction_full 0.996
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_diffrn_reflns_theta_full        66.596
_diffrn_reflns_theta_max         66.596
_diffrn_reflns_theta_min         5.374
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.910
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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    1.442
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.608
_refine_diff_density_min         -1.074
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3573
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0412
_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^)+(0.0526P)^2^+0.8411P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1082
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3380
_reflns_number_total             3573
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc09876c3.cif
_cod_data_source_block           zhaoqsh_0401
_cod_depositor_comments
'Adding full bibliography for 7125826--7125827.cif.'
_cod_original_cell_volume        1014.26(9)
_cod_database_code               7125826
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.61
_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:
 C10(H10), C11(H11), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C4(H4A,H4B), C7(H7A,H7B), C0AA(H0AA,H0AB), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C3AA(H3AA), C4AA(H4AA), C20(H20), C24(H24), C1(H1), C7AA(H7AA),
 C8(H8), C1AA(H1AA), C2AA(H2AA)
2.d Idealised Me refined as rotating group:
 C5AA(H5AA,H5AB,H5AC)
;
_shelx_res_checksum              14272
_olex2_date_sample_data_collection 2019-04-03
_olex2_submission_special_instructions 'No special instructions were received'