Photoredox/Nickel Dual Catalyzed Stereospecific Synthesis of Distal Alkenyl Ketones
Zhao, Tian-Tian; Yu, Wan-Lei; Feng, Zhitao; Qin, Hao-Ni; Zheng, Haixue; Xu, Peng-Fei; Chemical Communications  (2022) –; doi:10.1039/D1CC06566A

data_7129432
_publ_section_title
;
 Photoredox/Nickel Dual Catalyzed Stereospecific Synthesis of Distal
 Alkenyl Ketones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06566A
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C33 H44 O5'
_chemical_formula_sum            'C33 H44 O5'
_chemical_formula_weight         520.68
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-07
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-05-17 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.2610(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.16900(10)
_cell_length_b                   16.3425(3)
_cell_length_c                   10.9598(2)
_cell_measurement_reflns_used    7053
_cell_measurement_temperature    299.34(10)
_cell_measurement_theta_max      75.1820
_cell_measurement_theta_min      4.0350
_cell_volume                     1459.11(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.34(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.942
_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     -2.00  23.00   0.50    0.05    --   43.05 -19.00 -60.00   50
  2  \w     27.00  52.00   0.50    0.05    --   43.05-115.00 -62.00   50
  3  \w     50.00 109.00   0.50    0.10    --  109.26-115.00 -62.00  118
  4  \w     39.00  64.00   0.50    0.10    --  109.26 -61.00 -60.00   50
  5  \w     36.00 103.00   0.50    0.10    --  109.26 -77.00 -60.00  134
  6  \w     36.00  64.00   0.50    0.10    --  109.26 -61.00 -90.00   56
  7  \w     35.00  67.00   0.50    0.10    --  109.26 -61.00 -30.00   64
  8  \w     36.00  67.00   0.50    0.10    --  109.26 -61.00  60.00   62
  9  \w     97.00 141.00   0.50    0.10    --  109.26-167.00 152.00   88
 10  \w     49.00  89.00   0.50    0.10    --  109.26-167.00 152.00   80
 11  \w    -36.00  -6.00   0.50    0.05    --   43.05 -19.00 -60.00   60
 12  \w    -31.00  38.00   0.50    0.05    --   43.05 -37.00-180.00  138
 13  \w     89.00 114.00   0.50    0.10    --  109.26  45.00 -30.00   50
 14  \w    135.00 167.00   0.50    0.10    --  109.26  45.00 -30.00   64
 15  \w    104.00 129.00   0.50    0.10    --  109.26 115.00  27.00   50
 16  \w     48.00 117.00   0.50    0.05    --   43.05 167.00 172.00  138
 17  \w    -54.00 -25.00   0.50    0.10    -- -100.00  45.00-120.00   58
 18  \w    -50.00 -25.00   0.50    0.10    -- -100.00  45.00-180.00   50
 19  \w    -54.00 -26.00   0.50    0.10    -- -100.00  45.00-150.00   56
 20  \w    -52.00 -24.00   0.50    0.10    -- -100.00  45.00 -90.00   56
 21  \w    -58.00 -33.00   0.50    0.10    -- -100.00  61.00-120.00   50
 22  \w    -80.00 -55.00   0.50    0.05    --  -43.05 115.00  27.00   50
 23  \w    -91.00 -66.00   0.50    0.10    -- -100.00 115.00  27.00   50
 24  \w    -68.00 -29.00   0.50    0.10    -- -100.00  61.00  60.00   78
 25  \w    -54.00 -29.00   0.50    0.10    -- -100.00  45.00  60.00   50
 26  \w    -51.00 -26.00   0.50    0.10    -- -100.00  45.00 150.00   50
 27  \w   -115.00 -90.00   0.50    0.10    -- -100.00 167.00 172.00   50
 28  \w   -175.00-129.00   0.50    0.10    -- -100.00 -45.00 120.00   92
 29  \w   -119.00 -94.00   0.50    0.10    -- -100.00 -45.00 120.00   50
 30  \w   -111.00 -56.00   0.50    0.05    --  -43.05-167.00 152.00  110
 31  \w   -102.00 -77.00   0.50    0.10    -- -100.00-167.00 152.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0149375000
_diffrn_orient_matrix_UB_12      -0.0887899000
_diffrn_orient_matrix_UB_13      -0.0450527000
_diffrn_orient_matrix_UB_21      -0.0478906000
_diffrn_orient_matrix_UB_22      0.0280745000
_diffrn_orient_matrix_UB_23      -0.1320348000
_diffrn_orient_matrix_UB_31      0.1823238000
_diffrn_orient_matrix_UB_32      0.0146741000
_diffrn_orient_matrix_UB_33      -0.0201303000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9483
_diffrn_reflns_point_group_measured_fraction_full 0.855
_diffrn_reflns_point_group_measured_fraction_max 0.793
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.891
_diffrn_reflns_theta_min         4.045
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.619
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.185
_exptl_crystal_description       block
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1547 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         4821
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.945
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0403
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1253
_reflns_Friedel_coverage         0.625
_reflns_Friedel_fraction_full    0.701
_reflns_Friedel_fraction_max     0.634
_reflns_number_gt                4380
_reflns_number_total             4821
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06566a2.cif
_cod_data_source_block           zhaotiantian_0507-1
_cod_database_code               7129432
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.946
_reflns_odcompleteness_completeness 99.71
_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:
 C5(H5), C9(H9), C10(H10), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C7(H7A,H7B), C8(H8A,H8B), C12(H12A,H12B), C13(H13A,
 H13B), C14(H14A,H14B), C15(H15A,H15B), C17(H17A,H17B), C22(H22A,H22B),
 C23(H23A,H23B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C28(H28), C30(H30), C31(H31)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_shelx_res_checksum              2507
_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 1.637
_oxdiff_exptl_absorpt_empirical_full_min 0.725