Three-component reductive conjugate addition/aldol tandem reaction enabled by nickel/photoredox dual catalysis.
Zhao, Hongping; Yuan, Weiming; Chemical science 14 (2023) 1485–1490; doi:10.1039/d2sc06303d

data_1568265
_publ_section_title
;
 Three-component reductive conjugate addition/aldol tandem reaction
 enabled by nickel/photoredox dual catalysis.
;
_journal_issue                   6
_journal_name_full               'Chemical science'
_journal_page_first              1485
_journal_page_last               1490
_journal_paper_doi               10.1039/d2sc06303d
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C29 H33 N O2'
_chemical_formula_sum            'C29 H33 N O2'
_chemical_formula_weight         427.56
_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     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2df5jk
_audit_creation_date             2022-11-03
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-11-03 deposited with the CCDC.	2023-01-06 downloaded from the CCDC.
;
_cell_angle_alpha                79.360(2)
_cell_angle_beta                 75.595(2)
_cell_angle_gamma                79.481(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0904(3)
_cell_length_b                   12.0393(3)
_cell_length_c                   12.8065(3)
_cell_measurement_reflns_used    19506
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.0890
_cell_measurement_theta_min      3.7480
_cell_volume                     1175.11(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.975
_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     70.00  98.00   0.50    0.50    --   12.00  60.00  70.37   56
  2  \w    -11.00  65.00   0.50    0.50    --   12.00  60.00  70.37  152
  3  \w    -19.00  55.00   0.50    0.50    --   36.00 -45.00 -75.53  148
  4  \w    -51.00 -23.00   0.50    0.50    --   36.00 -45.00 -75.53   56
  5  \w     17.00  57.00   0.50    0.50    --   44.00  71.00 173.19   80
  6  \w     79.00 114.00   0.50    0.50    --   44.00  71.00 173.19   70
  7  \w     77.00 113.00   0.50    0.50    --   48.00  72.00-123.39   72
  8  \w     21.00  59.00   0.50    0.50    --   48.00  72.00-123.39   76
  9  \w     26.00  58.00   0.50    0.50    --   52.00  71.00 -27.89   64
 10  \w     29.00  69.00   0.50    0.50    --   56.00  71.00 -74.38   80
 11  \w     35.00  72.00   0.50    0.50    --   60.00  74.00  79.13   74
 12  \w     32.00  70.00   0.50    0.50    --   60.00  75.00  13.25   76
 13  \w     37.00  63.00   0.50    0.50    --   64.00  75.00  34.50   52
 14  \w     37.00  65.00   0.50    0.50    --   64.00  73.00 111.84   56
 15  \w     40.00  73.00   0.50    0.50    --   68.00  74.00 147.92   66
 16  \w     47.00  75.00   0.50    0.50    --   68.00  74.00  48.94   56
 17  \w     45.00  81.00   0.50    0.50    --   72.00  75.00 -64.17   72
 18  \w     45.00  80.00   0.50    0.50    --   72.00  72.00 -27.61   70
 19  \w     47.00  80.00   0.50    0.50    --   72.00  74.00 158.99   66
 20  \w    112.00 138.00   0.50    0.50    --   72.00  72.00 -27.61   52
 21  \w     45.00  85.00   0.50    0.50    --   72.00  74.00-101.62   80
 22  \w    116.00 157.00   0.50    0.50    --   72.00  75.00 -64.17   82
 23  \w     48.00  80.00   0.50    0.50    --   76.00  74.00-170.54   64
 24  \w     49.00  74.00   0.50    0.50    --   76.00  72.00-131.86   50
 25  \w     54.00  79.00   0.50    0.50    --   80.00  69.00-178.02   50
 26  \w    108.00 169.00   0.50    0.50    --   80.00  72.00   4.03  122
 27  \w     53.00  80.00   0.50    0.50    --   80.00  72.00   4.03   54
 28  \w    120.00 169.00   0.50    0.50    --   80.00  69.00-178.02   98
 29  \w      6.00 118.00   0.50    0.50    --   95.20 -61.00-180.00  224
 30  \w     73.00 162.00   0.50    0.50    --   95.20  61.00-180.00  178
 31  \w     85.00 111.00   0.50    0.50    --   95.20 -82.00 120.00   52
 32  \w     69.00 138.00   0.50    0.50    --   95.20  73.00  58.44  138
 33  \w     58.00 118.00   0.50    0.50    --   95.20 -82.00  30.00  120
 34  \w      6.00  34.00   0.50    0.50    --   95.20 -82.00  30.00   56
 35  \w     71.00 151.00   0.50    0.50    --   95.20  63.00 127.94  160
 36  \w     72.00 115.00   0.50    0.50    --   95.20  61.00-150.00   86
 37  \w     54.00 127.00   0.50    0.50    --   95.20 -82.00-180.00  146
 38  \w     72.00 143.00   0.50    0.50    --   95.20  61.00 -30.00  142
 39  \w      9.00  50.00   0.50    0.50    --   95.20 -82.00-180.00   82
 40  \w    125.00 150.00   0.50    0.50    --   95.20  61.00  90.00   50
 41  \w     75.00 117.00   0.50    0.50    --   95.20  61.00  90.00   84
 42  \w     72.00 136.00   0.50    0.50    --   95.20  61.00-120.00  128
 43  \w     74.00 102.00   0.50    0.50    --   95.20  53.00  63.15   56
 44  \w    137.00 185.00   0.50    0.50    --   95.20  71.00 -95.66   96
 45  \w     69.00 128.00   0.50    0.50    --   95.20  71.00 -95.66  118
 46  \w     69.00 120.00   0.50    0.50    --   95.20 -82.00 -60.00  102
 47  \w    152.00 183.00   0.50    0.50    --   95.20  66.00  20.06   62
 48  \w     73.00 147.00   0.50    0.50    --   95.20  66.00  20.06  148
 49  \w     75.00 182.00   0.50    0.50    --   95.20  58.00 109.85  214
 50  \w    134.00 184.00   0.50    0.50    --   95.20  61.00-150.00  100
 51  \w     16.00  41.00   0.50    0.50    --   95.20 -61.00  60.00   50
 52  \w     57.00 110.00   0.50    0.50    --   95.20 -61.00  60.00  106
 53  \w     72.00 128.00   0.50    0.50    --   95.20  61.00 -60.00  112
 54  \w      7.00  57.00   0.50    0.50    --   95.20 -82.00 120.00  100
 55  \w     83.00 146.00   0.50    0.50    --   95.20  45.00  12.66  126
 56  \w     13.00 110.00   0.50    0.50    --   95.20 -61.00 -60.00  194
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0196247000
_diffrn_orient_matrix_UB_12      -0.0491909000
_diffrn_orient_matrix_UB_13      0.1216434000
_diffrn_orient_matrix_UB_21      -0.1665532000
_diffrn_orient_matrix_UB_22      -0.0443576000
_diffrn_orient_matrix_UB_23      -0.0008625000
_diffrn_orient_matrix_UB_31      0.1064882000
_diffrn_orient_matrix_UB_32      -0.1136721000
_diffrn_orient_matrix_UB_33      -0.0310605000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0129
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25400
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.371
_diffrn_reflns_theta_min         3.602
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.580
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0077(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4669
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0345
_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^)+(0.0399P)^2^+0.4095P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.0897
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4522
_reflns_number_total             4669
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc06303d2.cif
_cod_data_source_block           20221102_zhp-195-1-1
_cod_depositor_comments
'Adding full bibliography for 1568263--1568265.cif.'
_cod_database_code               1568265
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.918
_shelx_estimated_absorpt_t_min   0.845
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C005(H005), C006(H006), C00E(H00G)
2.b Secondary CH2 refined with riding coordinates:
 C009(H00A,H00B), C00C(H00D,H00E), C00J(H00J,H00K), C00K(H00L,H00M), C00P(H00T,
 H00U), C00R(H00W,H00X)
2.c Aromatic/amide H refined with riding coordinates:
 C008(H008), C00A(H00C), C00D(H00F), C00G(H00H), C00I(H00I), C00L(H00N),
 C00M(H00O), C00O(H00S), C00Q(H00V), C00S(H00Y), C00T(H00Z), C00U(H00),
 C00V(H1), C00W(H2)
2.d Idealised Me refined as rotating group:
 C00N(H00P,H00Q,H00R)
2.e Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_shelx_res_checksum              42267
_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 1.902
_oxdiff_exptl_absorpt_empirical_full_min 0.682