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_1568264
_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.cc2df5fg
_audit_creation_date             2022-11-03
_audit_creation_method
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_audit_update_record
;
2022-11-03 deposited with the CCDC.	2023-01-06 downloaded from the CCDC.
;
_cell_angle_alpha                93.312(2)
_cell_angle_beta                 101.472(2)
_cell_angle_gamma                98.720(2)
_cell_formula_units_Z            2
_cell_length_a                   9.5665(3)
_cell_length_b                   10.3386(2)
_cell_length_c                   12.4055(3)
_cell_measurement_reflns_used    19899
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4470
_cell_measurement_theta_min      4.3240
_cell_volume                     1183.64(5)
_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 1.3 (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    '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 0.997
_diffrn_measured_fraction_theta_max 0.983
_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    -86.00 -51.00   0.50    0.50    --    0.00 -38.00 120.00   70
  2  \w    -49.00  16.00   0.50    0.50    --    0.00 -38.00 -60.00  130
  3  \w    -39.00  29.00   0.50    0.50    --    0.00 -77.00-180.00  136
  4  \w     45.00  77.00   0.50    0.50    --    0.00  57.00-150.00   64
  5  \w     55.00  86.00   0.50    0.50    --    0.00  38.00-180.00   62
  6  \w    -42.00  15.00   0.50    0.50    --    0.00 -38.00 120.00  114
  7  \w      7.00  33.00   0.50    0.50    --    0.00  38.00-180.00   52
  8  \w    -20.00  89.00   0.50    0.50    --    0.00  57.00 -30.00  218
  9  \w    -19.00  15.00   0.50    0.50    --    0.00  57.00-150.00   68
 10  \w     -2.00  73.00   0.50    0.50    --    0.00  57.00 -90.00  150
 11  \w    -86.00 -61.00   0.50    0.50    --    0.00 -38.00 -60.00   50
 12  \w     67.00  92.00   0.50    0.50    --   94.60  73.00 -34.32   50
 13  \w     68.00 111.00   0.50    0.50    --   94.60  70.00 -23.48   86
 14  \w     68.00  94.00   0.50    0.50    --   94.60  69.00-168.03   52
 15  \w     67.00  92.00   0.50    0.50    --   94.60  73.00 -67.73   50
 16  \w    117.00 143.00   0.50    0.50    --   94.60  59.00 -94.93   52
 17  \w     68.00 144.00   0.50    0.50    --   94.60  70.00  84.17  152
 18  \w     67.00  93.00   0.50    0.50    --   94.60  73.00  31.78   52
 19  \w     67.00  93.00   0.50    0.50    --   94.60  74.00-167.54   52
 20  \w     72.00 106.00   0.50    0.50    --   94.60  59.00 -94.93   68
 21  \w     74.00 100.00   0.50    0.50    --   94.60  58.00 -72.30   52
 22  \w     68.00 158.00   0.50    0.50    --   94.60  71.00  43.28  180
 23  \w     66.00  95.00   0.50    0.50    --   94.60  75.00 -11.60   58
 24  \w     30.00  56.00   0.50    0.50    --   94.60 -82.00   0.00   52
 25  \w     85.00 126.00   0.50    0.50    --   94.60 -82.00   0.00   82
 26  \w      5.00 123.00   0.50    0.50    --   94.60 -82.00-180.00  236
 27  \w      5.00 126.00   0.50    0.50    --   94.60 -82.00 -60.00  242
 28  \w      5.00 125.00   0.50    0.50    --   94.60 -82.00  90.00  240
 29  \w     71.00  97.00   0.50    0.50    --   94.60  61.00 150.00   52
 30  \w     71.00  97.00   0.50    0.50    --   94.60  61.00-180.00   52
 31  \w     71.00 126.00   0.50    0.50    --   94.60  68.00   8.39  110
 32  \w     68.00  98.00   0.50    0.50    --   94.60  70.00  62.20   60
 33  \w     72.00  97.00   0.50    0.50    --   94.60  55.00 177.06   50
 34  \w     71.00 108.00   0.50    0.50    --   94.60  61.00-120.00   74
 35  \w     67.00 129.00   0.50    0.50    --   94.60  73.00  66.26  124
 36  \w     75.00 175.00   0.50    0.50    --   94.60  45.00 -60.00  200
 37  \w      6.00  83.00   0.50    0.50    --   94.60 -61.00  90.00  154
 38  \w     71.00 184.00   0.50    0.50    --   94.60  61.00 -30.00  226
 39  \w     71.00 101.00   0.50    0.50    --   94.60  61.00  30.00   60
 40  \w    104.00 161.00   0.50    0.50    --   94.60  61.00  30.00  114
 41  \w     15.00 118.00   0.50    0.50    --   94.60 -61.00 -60.00  206
 42  \w     66.00 103.00   0.50    0.50    --   94.60  74.00-153.23   74
 43  \w     72.00 170.00   0.50    0.50    --   94.60  58.00-157.93  196
 44  \w     77.00 174.00   0.50    0.50    --   94.60  45.00-180.00  194
 45  \w     71.00  97.00   0.50    0.50    --   94.60  61.00 120.00   52
 46  \w     72.00 112.00   0.50    0.50    --   94.60  55.00-102.29   80
 47  \w     19.00  45.00   0.50    0.50    --   94.60 -61.00-180.00   52
 48  \w     54.00 108.00   0.50    0.50    --   94.60 -61.00-180.00  108
 49  \w     67.00  92.00   0.50    0.50    --   94.60  71.00  26.34   50
 50  \w     75.00 158.00   0.50    0.50    --   94.60  45.00 150.00  166
 51  \w    159.00 184.00   0.50    0.50    --   94.60  69.00-168.03   50
 52  \w    155.00 180.00   0.50    0.50    --   94.60  70.00 -23.48   50
 53  \w     70.00 129.00   0.50    0.50    --   94.60  63.00 -45.24  118
 54  \w    137.00 162.00   0.50    0.50    --   94.60  46.00 132.33   50
 55  \w     75.00 101.00   0.50    0.50    --   94.60  46.00 132.33   52
;
_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      0.0605415000
_diffrn_orient_matrix_UB_12      -0.0460379000
_diffrn_orient_matrix_UB_13      0.1132600000
_diffrn_orient_matrix_UB_21      -0.1389413000
_diffrn_orient_matrix_UB_22      0.0208458000
_diffrn_orient_matrix_UB_23      0.0387516000
_diffrn_orient_matrix_UB_31      -0.0693014000
_diffrn_orient_matrix_UB_32      -0.1426936000
_diffrn_orient_matrix_UB_33      -0.0431337000
_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  0.0233
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            26024
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.763
_diffrn_reflns_theta_min         3.651
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.576
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75973
_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    1.200
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4707
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0367
_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^)+(0.0473P)^2^+0.3719P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.0944
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4556
_reflns_number_total             4707
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc06303d2.cif
_cod_data_source_block           20220322_zhp-195-1-2
_cod_depositor_comments
'Adding full bibliography for 1568263--1568265.cif.'
_cod_database_code               1568264
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.903
_shelx_estimated_absorpt_t_min   0.824
_reflns_odcompleteness_completeness 99.65
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C008(H008), C009(H009), C00C(H00C)
2.b Secondary CH2 refined with riding coordinates:
 C00I(H00I,H00J), C00L(H00M,H00N), C00P(H00R,H00S), C00U(H00X,H00Y), C00V(H00Z,
 H), C00W(H00,HA)
2.c Aromatic/amide H refined with riding coordinates:
 C007(H007), C00B(H00B), C00E(H00E), C00F(H00F), C00H(H00H), C00J(H00K),
 C00K(H00L), C00M(H00O), C00N(H00P), C00O(H00Q), C00Q(H00T), C00R(H00U),
 C00S(H00V), C00T(H00W)
2.d Idealised Me refined as rotating group:
 C00G(H00A,H00D,H00G)
2.e Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_shelx_res_checksum              4409
_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 1.578
_oxdiff_exptl_absorpt_empirical_full_min 0.754