Native group-directed double Heck arylation of internal alkenes via selective β-H elimination
Wang, Jiali; Luan, Runze; Liu, Tianming; Liu, Siqing; Du, Yu; Su, Weiping; Chemical Communications 61 (2025) 6526–6529; doi:10.1039/D5CC00821B

data_7134367
_publ_section_title
;
 Native group-directed double Heck arylation of internal alkenes via
 selective \b-H elimination
;
_journal_issue                   35
_journal_name_full               'Chemical Communications'
_journal_page_first              6526
_journal_page_last               6529
_journal_paper_doi               10.1039/D5CC00821B
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C31 H26 N2 O6'
_chemical_formula_sum            'C31 H26 N2 O6'
_chemical_formula_weight         522.54
_chemical_name_systematic        WJL20250220
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2025-02-20
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-02-20 deposited with the CCDC.	2025-04-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.459(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.01910(10)
_cell_length_b                   21.3231(3)
_cell_length_c                   20.4562(3)
_cell_measurement_reflns_used    14910
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.3980
_cell_measurement_theta_min      2.1200
_cell_volume                     2625.38(7)
_computing_cell_refinement       'CrysAlisPro 1.171.43.118a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.118a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.118a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_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   -118.00 -89.00   0.50    0.80    --  -47.77-125.00-150.00   58
  2  \w   -105.00 -36.00   0.50    4.10    -- -105.00 117.00  52.00  138
  3  \w    -10.00  22.00   0.50    0.80    --   47.77 -19.00 -60.00   64
  4  \w    142.00 176.00   0.50    4.10    --  108.17  94.00 -28.00   68
  5  \w     43.00 105.00   0.50    4.10    --  108.17-125.00 -60.00  124
  6  \w   -121.00 -47.00   0.50    0.80    --  -47.77 -31.00  38.00  148
  7  \w   -168.00 -98.00   0.50    4.10    -- -105.00 -31.00  38.00  140
  8  \w    -67.00 -40.00   0.50    4.10    -- -105.00  61.00   0.00   54
  9  \w    -68.00 -39.00   0.50    4.10    -- -105.00  61.00  60.00   58
 10  \w    -71.00 -36.00   0.50    4.10    -- -105.00  61.00 150.00   70
 11  \w    -15.00  26.00   0.50    0.80    --  -47.77  19.00 -30.00   82
 12  \w    -67.00 -41.00   0.50    4.10    -- -105.00  61.00-180.00   52
 13  \w     50.00 119.00   0.50    0.80    --   47.77 160.00-155.00  138
 14  \w    -64.00 -33.00   0.50    0.80    --  -47.77 -44.00 -37.87   62
 15  \w    -78.00 -33.00   0.50    0.80    --  -47.77 -38.00-150.00   90
 16  \w    -50.00 -24.00   0.50    0.80    --  -47.77 -77.00  90.00   52
 17  \w    -58.00 -24.00   0.50    0.80    --  -47.77 -77.00  30.00   68
 18  \w    -68.00 -32.00   0.50    0.80    --  -47.77 -46.00  19.44   72
 19  \w   -119.00 -87.00   0.50    0.80    --  -47.77 -77.00  30.00   64
 20  \w   -103.00 -24.00   0.50    0.80    --  -47.77 -77.00 -30.00  158
 21  \w   -112.00 -24.00   0.50    0.80    --  -47.77 -77.00 120.00  176
 22  \w    -99.00 -32.00   0.50    0.80    --  -47.77 -57.00 150.00  134
 23  \w    -65.00 -25.00   0.50    0.80    --  -47.77 -77.00-180.00   80
 24  \w    -68.00 -24.00   0.50    0.80    --  -47.77 -77.00-120.00   88
 25  \w    -67.00 -33.00   0.50    0.80    --  -47.77 -57.00 -30.00   68
 26  \w    -53.00 -25.00   0.50    0.80    --  -47.77 -77.00-150.00   56
 27  \w    -84.00 -24.00   0.50    0.80    --  -47.77 -77.00 -90.00  120
 28  \w    -74.00 -33.00   0.50    0.80    --  -47.77 -44.00 167.68   82
 29  \w    -17.00   9.00   0.50    0.80    --   47.77 -57.00-180.00   52
 30  \w     37.00  64.00   0.50    0.80    --   47.77 -57.00-180.00   54
 31  \w     25.00  51.00   0.50    0.80    --   47.77  77.00 -30.00   52
 32  \w     39.00  91.00   0.50    0.80    --   47.77-125.00-150.00  104
 33  \w     14.00  89.00   0.50    0.80    --   47.77-125.00   0.00  150
 34  \w   -107.00 -80.00   0.50    3.80    -- -105.00 -79.00 -44.41   54
 35  \w   -163.00-137.00   0.50    3.80    -- -105.00 -79.00 -44.41   52
 36  \w   -113.00 -87.00   0.50    3.80    -- -105.00 -63.00-148.30   52
 37  \w   -156.00-131.00   0.50    3.80    -- -105.00 -77.00 -30.00   50
 38  \w   -108.00 -82.00   0.50    3.80    -- -105.00 -77.00 150.00   52
 39  \w   -174.00 -83.00   0.50    3.80    -- -105.00 -72.00-102.84  182
 40  \w   -107.00 -81.00   0.50    3.80    -- -105.00 -77.00 -30.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0456454000
_diffrn_orient_matrix_UB_12      0.0705939000
_diffrn_orient_matrix_UB_13      0.0084562000
_diffrn_orient_matrix_UB_21      0.0977963000
_diffrn_orient_matrix_UB_22      0.0126671000
_diffrn_orient_matrix_UB_23      -0.0681206000
_diffrn_orient_matrix_UB_31      -0.2320833000
_diffrn_orient_matrix_UB_32      -0.0085536000
_diffrn_orient_matrix_UB_33      -0.0310345000
_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  0.0507
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            26692
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        66.582
_diffrn_reflns_theta_max         66.582
_diffrn_reflns_theta_min         2.994
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.118a (Rigaku Oxford Diffraction, 2024)
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    1.322
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         4470
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0517
_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^)+(0.0556P)^2^+0.8665P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1339
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3741
_reflns_number_total             4470
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc00821b2.cif
_cod_data_source_block           wjl20250220_auto
_cod_depositor_comments          'Adding full bibliography for 7134367.cif.'
_cod_database_code               7134367
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHON
_chemical_oxdiff_usercomment     CHONSbSeCu
_shelx_estimated_absorpt_t_max   0.863
_shelx_estimated_absorpt_t_min   0.751
_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
2.a Ternary CH refined with riding coordinates:
 C26(H26)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b), C13(H13a,H13b)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C14(H14), C18(H18), C28(H28), C30(H30), C31(H31), C2(H2), C17(H17),
 C19(H19), C5(H5), C21(H21), C11(H11), C23(H23), C3(H3), C25(H25), C27(H27),
 C7(H7), C29(H29)
2.d Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c)
;
_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 1.456
_oxdiff_exptl_absorpt_empirical_full_min 0.419