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_1568310
_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         'C28 H32 O2'
_chemical_formula_sum            'C28 H32 O2'
_chemical_formula_weight         400.53
_chemical_name_systematic        1
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_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
;
2022-09-27 deposited with the CCDC.	2023-01-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.304(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.9673(7)
_cell_length_b                   15.1856(5)
_cell_length_c                   18.5806(8)
_cell_measurement_reflns_used    11817
_cell_measurement_temperature    293
_cell_measurement_theta_max      67.8060
_cell_measurement_theta_min      2.4550
_cell_volume                     4933.6(3)
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -42.00  69.00   0.50    1.00    --   42.30 -82.00-150.00  222
  2  \w    -28.00  -2.00   0.50    1.00    --   42.30 -82.00  60.00   52
  3  \w     16.00  70.00   0.50    1.00    --   42.30 -82.00 -90.00  108
  4  \w     24.00  93.00   0.50    1.00    --   42.30  65.00  30.00  138
  5  \w     13.00  72.00   0.50    1.00    --   42.30 -43.00-120.00  118
  6  \w      6.00  70.00   0.50    1.00    --   42.30 -82.00  60.00  128
  7  \w     21.00  64.00   0.50    1.00    --   42.30  65.00 120.00   86
  8  \w     19.00  49.00   0.50    1.00    --   42.30  65.00 -30.00   60
  9  \w     43.00  68.00   0.50    1.00    --   42.30 -77.00-150.00   50
 10  \w     -9.00  65.00   0.50    1.00    --   42.30 -82.00-180.00  148
 11  \w    -46.00   7.00   0.50    1.00    --   42.30 -54.00 120.00  106
 12  \w     10.00  70.00   0.50    1.00    --   42.30 -82.00   0.00  120
 13  \w    -47.00   2.00   0.50    1.00    --   42.30 -82.00   0.00   98
 14  \w    -30.00  -4.00   0.50    1.00    --   42.30 -43.00-120.00   52
 15  \w     44.00  69.00   0.50    1.00    --   42.30 -82.00  90.00   50
 16  \w     42.00  67.00   0.50    1.00    --   42.30 -77.00 -90.00   50
 17  \w     42.00  67.00   0.50    1.00    --   42.30 -77.00 120.00   50
 18  \w      9.00  34.00   0.50    1.00    --   42.30 -77.00-150.00   50
 19  \w     31.00  86.00   0.50    1.00    --   42.30  43.00 120.00  110
 20  \w    -24.00   1.00   0.50    1.00    --   42.30 -77.00  90.00   50
 21  \w    100.00 125.00   0.50    1.00    --   42.30  43.00 120.00   50
 22  \w    -42.00   5.00   0.50    1.00    --   42.30 -82.00 -90.00   94
 23  \w     22.00 120.00   0.50    1.00    --   42.30  65.00-180.00  196
 24  \w     -9.00  16.00   0.50    1.00    --   42.30 -77.00 120.00   50
 25  \w     10.00  70.00   0.50    1.00    --   42.30 -43.00-180.00  120
 26  \w      5.00  34.00   0.50    1.50    --   93.70 -82.00 -90.00   58
 27  \w     59.00  96.00   0.50    1.50    --   93.70 -82.00 -30.00   74
 28  \w     29.00  98.00   0.50    1.50    --   93.70 -82.00-150.00  138
 29  \w     78.00 110.00   0.50    1.50    --   93.70 -33.00 120.00   64
 30  \w     26.00 114.00   0.50    1.50    --   93.70 -82.00  30.00  176
 31  \w      6.00  35.00   0.50    1.50    --   93.70 -33.00 120.00   58
 32  \w      8.00 111.00   0.50    1.50    --   93.70 -59.00 -90.00  206
 33  \w      4.00 180.00   0.50    1.50    --   93.70  -8.00 -90.00  352
 34  \w     12.00  99.00   0.50    1.50    --   93.70 -82.00 120.00  174
 35  \w    117.00 183.00   0.50    1.50    --   93.70  68.00 -90.00  132
 36  \w     73.00  98.00   0.50    1.50    --   93.70  68.00 -90.00   50
 37  \w     70.00  96.00   0.50    1.50    --   93.70 -82.00 -60.00   52
 38  \w      4.00  46.00   0.50    1.50    --   93.70 -42.00  60.00   84
 39  \w    135.00 183.00   0.50    1.50    --   93.70  50.00 -30.00   96
 40  \w     75.00 100.00   0.50    1.50    --   93.70 -82.00   0.00   50
 41  \w     50.00  96.00   0.50    1.50    --   93.70 -82.00 150.00   92
 42  \w      9.00  93.00   0.50    1.50    --   93.70 -82.00-180.00  168
 43  \w    152.00 183.00   0.50    1.50    --   93.70  68.00-180.00   62
 44  \w    114.00 139.00   0.50    1.50    --   93.70  68.00-180.00   50
 45  \w     49.00 101.00   0.50    1.50    --   93.70 -82.00 -90.00  104
 46  \w     99.00 124.00   0.50    1.50    --   93.70  68.00-150.00   50
 47  \w      8.00 120.00   0.50    1.50    --   93.70 -33.00 -90.00  224
 48  \w     10.00  98.00   0.50    1.50    --   93.70 -82.00-120.00  176
 49  \w     73.00  98.00   0.50    1.50    --   93.70 -82.00  70.41   50
 50  \w     42.00  91.00   0.50    1.50    --   93.70 -82.00  90.00   98
 51  \w     16.00  65.00   0.50    1.50    --   93.70 -82.00  70.41   98
;
_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      -0.0442038000
_diffrn_orient_matrix_UB_12      0.0251858000
_diffrn_orient_matrix_UB_13      -0.0784437000
_diffrn_orient_matrix_UB_21      -0.0738023000
_diffrn_orient_matrix_UB_22      0.0100499000
_diffrn_orient_matrix_UB_23      0.0282074000
_diffrn_orient_matrix_UB_31      0.0190211000
_diffrn_orient_matrix_UB_32      0.0977921000
_diffrn_orient_matrix_UB_33      0.0173211000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1064
_diffrn_reflns_av_unetI/netI     0.0869
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            49159
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        63.687
_diffrn_reflns_theta_max         63.687
_diffrn_reflns_theta_min         3.085
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.510
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.01903
_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    1.078
_exptl_crystal_description       block
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     549
_refine_ls_number_reflns         8104
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.1251
_refine_ls_R_factor_gt           0.0955
_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^)+(0.1891P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2689
_refine_ls_wR_factor_ref         0.3144
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4800
_reflns_number_total             8104
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc05894d2.cif
_cod_data_source_block           2j-danjing4_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            'C56 H64 O4'
_cod_original_formula_weight         801.07
_cod_original_formula_moiety         '2(C28 H32 O2)'
_cod_original_formula_units_Z            4
_cod_database_code               1568310
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.970
_diffrn_oxdiff_digest_frames
;
014f011bcc05c801f8f6b8b718d8b2f1df00028aafc
;
_diffrn_oxdiff_digest_hkl
;
014fc68681347458031dddd37c28cc0746b8ab
;
_reflns_odcompleteness_completeness 99.86
_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:
 C16(H16), C44(H44)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C13(H13A,H13B), C14(H14A,H14B), C37(H37A,H37B),
 C38(H38A,H38B), C41(H41A,H41B), C42(H42A,H42B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C6(H6), C7(H7), C18(H18), C19(H19), C21(H21), C22(H22),
 C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C31(H31), C32(H32), C33(H33),
  C34(H34), C46(H46), C47(H47), C49(H49), C50(H50), C52(H52), C53(H53),
 C54(H54), C55(H55), C56(H56)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C11(H11A,H11B,H11C), C15(H15A,H15B,H15C), C29(H29A,H29B,
 H29C), C36(H36A,H36B,H36C), C43(H43A,H43B,H43C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3)
;
_shelx_res_checksum              46167
_shelx_hkl_checksum              59096
_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 22.635
_oxdiff_exptl_absorpt_empirical_full_min 0.404