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_1568263
_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         'C23 H22 O3'
_chemical_formula_sum            'C23 H22 O3'
_chemical_formula_weight         346.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2df523
_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                90
_cell_angle_beta                 96.250(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6143(3)
_cell_length_b                   31.7341(6)
_cell_length_c                   5.47460(10)
_cell_measurement_reflns_used    7072
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.7610
_cell_measurement_theta_min      4.2050
_cell_volume                     1833.08(7)
_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 0.999
_diffrn_measured_fraction_theta_max 0.986
_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    -33.00  18.00   0.50    0.50    --    0.00 -82.00  60.00  102
  2  \w    -14.00  30.00   0.50    0.50    --    0.00 -82.00-180.00   88
  3  \w    -20.00  27.00   0.50    0.50    --    0.00 -82.00 120.00   94
  4  \w    -45.00   3.00   0.50    0.50    --    0.00 -77.00 -90.00   96
  5  \w    -30.00  31.00   0.50    0.50    --    0.00 -82.00 -30.00  122
  6  \w     59.00 112.00   0.50    2.00    --   95.80 -30.00 -90.00  106
  7  \w     27.00 127.00   0.50    2.00    --   95.80 -82.00 -90.00  200
  8  \w     95.00 127.00   0.50    2.00    --   95.80  82.00   0.00   64
  9  \w      7.00 118.00   0.50    2.00    --   95.80 -61.00  60.00  222
 10  \w    101.00 127.00   0.50    2.00    --   95.80  82.00 120.00   52
 11  \w     71.00 104.00   0.50    2.00    --   95.80 -82.00  60.00   66
 12  \w    109.00 183.00   0.50    2.00    --   95.80  30.00   0.00  148
 13  \w     72.00 184.00   0.50    2.00    --   95.80  15.00 120.00  224
 14  \w     86.00 113.00   0.50    2.00    --   95.80 -82.00 120.00   54
 15  \w     85.00 116.00   0.50    2.00    --   95.80 -82.00 -30.00   62
 16  \w      6.00  77.00   0.50    2.00    --   95.80 -61.00-150.00  142
 17  \w     11.00 119.00   0.50    2.00    --   95.80 -82.00-150.00  216
 18  \w     80.00 105.00   0.50    2.00    --   95.80 -82.00  30.00   50
 19  \w     10.00  49.00   0.50    2.00    --   95.80 -82.00  60.00   78
 20  \w     41.00 115.00   0.50    2.00    --   95.80 -45.00  60.00  148
 21  \w     75.00 100.00   0.50    2.00    --   95.80 -82.00-180.00   50
 22  \w     95.00 120.00   0.50    2.00    --   95.80 -82.00   0.00   50
 23  \w      7.00 105.00   0.50    2.00    --   95.80 -61.00 -90.00  196
;
_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      0.1431662000
_diffrn_orient_matrix_UB_12      0.0077652000
_diffrn_orient_matrix_UB_13      0.0620406000
_diffrn_orient_matrix_UB_21      0.0208020000
_diffrn_orient_matrix_UB_22      -0.0474485000
_diffrn_orient_matrix_UB_23      0.0487949000
_diffrn_orient_matrix_UB_31      0.0197967000
_diffrn_orient_matrix_UB_32      -0.0067365000
_diffrn_orient_matrix_UB_33      -0.2718283000
_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  0.0535
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            17080
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.516
_diffrn_reflns_theta_min         2.785
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.653
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47173
_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    1.255
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3697
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0614
_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^)+(0.0701P)^2^+1.4251P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1567
_refine_ls_wR_factor_ref         0.1623
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3193
_reflns_number_total             3697
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc06303d2.cif
_cod_data_source_block           0322_zhp-152-2
_cod_depositor_comments
'Adding full bibliography for 1568263--1568265.cif.'
_cod_database_code               1568263
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.891
_shelx_estimated_absorpt_t_min   0.804
_reflns_odcompleteness_completeness 99.79
_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:
 C006(H006), C007(H007)
2.b Secondary CH2 refined with riding coordinates:
 C00C(H00E,H00F)
2.c Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00B(H00D), C00E(H00G), C00F(H00H), C00G(H00I),
 C00I(H00J), C00J(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P), C00Q(H00Q)
2.d Idealised Me refined as rotating group:
 C00A(H00A,H00B,H00C)
2.e Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_shelx_res_checksum              51113
_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 3.209
_oxdiff_exptl_absorpt_empirical_full_min 0.545