Ni-catalyzed arylation of alkynes with organoboronic acids and aldehydes to access stereodefined allylic alcohols.
Tao, Si-Chen; Meng, Fan-Cheng; Wang, Tie; Zheng, Yan-Long; Chemical science 14 (2023) 2040–2045; doi:10.1039/d2sc05894d

data_1568309
_publ_section_title
;
 Ni-catalyzed arylation of alkynes with organoboronic acids and aldehydes
 to access stereodefined allylic alcohols.
;
_journal_issue                   8
_journal_name_full               'Chemical science'
_journal_page_first              2040
_journal_page_last               2045
_journal_paper_doi               10.1039/d2sc05894d
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C23 H27 F3 O3'
_chemical_formula_sum            'C23 H27 F3 O3'
_chemical_formula_weight         408.44
_chemical_name_systematic        1
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-09-24 deposited with the CCDC.	2023-01-20 downloaded from the CCDC.
;
_cell_angle_alpha                84.924(3)
_cell_angle_beta                 76.057(2)
_cell_angle_gamma                69.976(2)
_cell_formula_units_Z            4
_cell_length_a                   12.5957(3)
_cell_length_b                   13.0422(4)
_cell_length_c                   15.1090(5)
_cell_measurement_reflns_used    7139
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      59.7040
_cell_measurement_theta_min      3.0010
_cell_volume                     2263.24(12)
_computing_cell_refinement       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_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     14.00  79.00   0.50    1.00    --   42.30  43.00   0.00  130
  2  \w    -45.00  30.00   0.50    1.00    --   42.30 -77.00  90.00  150
  3  \w     31.00 130.00   0.50    1.00    --   42.30  77.00 120.00  198
  4  \w     85.00 122.00   0.50    1.00    --   42.30  43.00   0.00   74
  5  \w     36.00  66.00   0.50    1.00    --   42.30 -82.00-120.00   60
  6  \w     80.00 132.00   0.50    1.00    --   42.30  77.00-120.00  104
  7  \w    -11.00  69.00   0.50    1.00    --   42.30 -82.00-180.00  160
  8  \w    -43.00  17.00   0.50    1.00    --   42.30 -65.00 -90.00  120
  9  \w     -5.00  27.00   0.50    1.00    --   42.30 -82.00-120.00   64
 10  \w     34.00  63.00   0.50    1.00    --   42.30  77.00-120.00   58
 11  \w    -10.00  41.00   0.50    1.00    --   42.30 -77.00-180.00  102
 12  \w    -10.00  39.00   0.50    1.00    --   42.30 -65.00   0.00   98
 13  \w     41.00  69.00   0.50    1.00    --   42.30 -82.00  60.00   56
 14  \w    -46.00  13.00   0.50    1.00    --   42.30 -82.00  60.00  118
 15  \w    -39.00 -14.00   0.50    1.00    --   42.30 -82.00-120.00   50
 16  \w     34.00  69.00   0.50    1.00    --   42.30 -82.00 -60.00   70
 17  \w    -29.00  -4.00   0.50    1.00    --   42.30 -77.00 -60.00   50
 18  \w     41.00  66.00   0.50    1.00    --   42.30 -65.00 -90.00   50
 19  \w     28.00  62.00   0.50    1.00    --   42.30 -82.00  30.00   68
 20  \w     72.00  98.00   0.50    1.50    --   93.70 -82.00 -60.00   52
 21  \w     66.00 183.00   0.50    1.50    --   93.70  82.00 -60.00  234
 22  \w    155.00 181.00   0.50    1.50    --   93.70  59.00 150.00   52
 23  \w    129.00 163.00   0.50    1.50    --   93.70  33.00 -90.00   68
 24  \w     60.00 104.00   0.50    1.50    --   93.70  33.00 -90.00   88
 25  \w      5.00  99.00   0.50    1.50    --   93.70 -82.00-150.00  188
 26  \w      4.00 104.00   0.50    1.50    --   93.70 -82.00 120.00  200
 27  \w    134.00 160.00   0.50    1.50    --   93.70  68.00-180.00   52
 28  \w      4.00 111.00   0.50    1.50    --   93.70 -82.00   0.00  214
 29  \w     71.00  97.00   0.50    1.50    --   93.70  68.00-180.00   52
 30  \w      4.00  67.00   0.50    1.50    --   93.70 -82.00  60.00  126
 31  \w      7.00  94.00   0.50    1.50    --   93.70 -82.00 -30.00  174
 32  \w     31.00  96.00   0.50    1.50    --   93.70 -82.00-120.00  130
 33  \w     66.00 183.00   0.50    1.50    --   93.70  33.00-150.00  234
 34  \w     23.00  98.00   0.50    1.50    --   93.70 -82.00  90.00  150
 35  \w    114.00 183.00   0.50    1.50    --   93.70  33.00 150.00  138
 36  \w     79.00 105.00   0.50    1.50    --   93.70 -82.00 -90.00   52
 37  \w    117.00 182.00   0.50    1.50    --   93.70  59.00  60.00  130
 38  \w     79.00 105.00   0.50    1.50    --   93.70 -82.00-180.00   52
 39  \w     65.00  90.00   0.50    1.50    --   93.70  33.00 150.00   50
 40  \w      4.00  70.00   0.50    1.50    --   93.70 -82.00 -90.00  132
 41  \w     71.00  96.00   0.50    1.50    --   93.70 -82.00 150.00   50
 42  \w     58.00 107.00   0.50    1.50    --   93.70 -82.00  30.00   98
 43  \w     74.00  99.00   0.50    1.50    --   93.70 -82.00  60.00   50
 44  \w     66.00  91.00   0.50    1.50    --   93.70  59.00  60.00   50
 45  \w     91.00 183.00   0.50    1.50    --   93.70  77.00 -90.00  184
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II 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      0.0299810000
_diffrn_orient_matrix_UB_12      -0.0847192000
_diffrn_orient_matrix_UB_13      -0.0748900000
_diffrn_orient_matrix_UB_21      -0.0330545000
_diffrn_orient_matrix_UB_22      0.0928935000
_diffrn_orient_matrix_UB_23      -0.0691620000
_diffrn_orient_matrix_UB_31      0.1259335000
_diffrn_orient_matrix_UB_32      0.0002477000
_diffrn_orient_matrix_UB_33      -0.0254145000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21866
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        66.582
_diffrn_reflns_theta_max         66.581
_diffrn_reflns_theta_min         3.014
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.794
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56374
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.89a (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    1.199
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.724
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.220
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     534
_refine_ls_number_reflns         7780
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.220
_refine_ls_R_factor_all          0.1139
_refine_ls_R_factor_gt           0.0881
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2964
_refine_ls_wR_factor_ref         0.3349
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4776
_reflns_number_total             7780
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc05894d2.cif
_cod_data_source_block           2j-3_auto
_cod_depositor_comments
;
Adding full bibliography for 1568308--1568310.cif.

2025-06-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C46 H54 F6 O6'
_cod_original_formula_weight         816.89
_cod_original_formula_moiety         '2(C23 H27 F3 O3)'
_cod_original_formula_units_Z            2
_cod_database_code               1568309
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.954
_diffrn_oxdiff_digest_frames
;
01b620c7b376e31582fd8e1b8be70d562900027c3dd
;
_diffrn_oxdiff_digest_hkl
;
01d922bc0fe4111cff4d9766501d8cae16bfa5
;
_reflns_odcompleteness_completeness 97.26
_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:
 C8(H8), C31(H31)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C33(H33A,H33B), C10(H10A,H10B), C14(H14A,H14B), C34(H34A,
 H34B), C37(H37A,H37B), C38(H38A,H38B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C5(H5), C30(H30), C22(H22), C19(H19), C20(H20), C41(H41), C28(H28),
 C25(H25), C7(H7), C4(H4), C45(H45), C42(H42), C2(H2A), C44(H44), C27(H27)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C23(H23A,H23B,H23C), C16(H16A,H16B,H16C), C35(H35A,H35B,
 H35C), C39(H39A,H39B,H39C), C46(H46A,H46B,H46C)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5A)
;
_shelx_res_checksum              81123
_shelx_hkl_checksum              25811
_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 2.120
_oxdiff_exptl_absorpt_empirical_full_min 0.708