Copper-catalyzed asymmetric carbonylative hydroallylation of vinylarenes
Shao, Sufang; Yuan, Yang; Schmoll, Alban; Wu, Xiao-Feng; Chemical Science 16 (2025) 10951–10956; doi:10.1039/D5SC02421H

data_1574638
_publ_section_title
;
 Copper-catalyzed asymmetric carbonylative hydroallylation of vinylarenes
;
_journal_issue                   24
_journal_name_full               'Chemical Science'
_journal_page_first              10951
_journal_page_last               10956
_journal_paper_doi               10.1039/D5SC02421H
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C13 H16 O2'
_chemical_formula_sum            'C13 H16 O2'
_chemical_formula_weight         204.26
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-12-30
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-12-31 deposited with the CCDC.	2025-05-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.827(13)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.9792(10)
_cell_length_b                   6.2593(6)
_cell_length_c                   11.4802(13)
_cell_measurement_reflns_used    1275
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      63.7070
_cell_measurement_theta_min      5.3140
_cell_volume                     598.97(12)
_computing_cell_refinement       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4070
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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    -88.00 -63.00   1.00    1.18    --  -42.12-178.00-120.00   25
  2  \w     20.00 116.00   1.00    1.18    --   42.12  37.00 -30.00   96
  3  \w     44.00 107.00   1.00    1.18    --   42.12 178.00 150.00   63
  4  \w     73.00  98.00   1.00    4.71    --   92.50  30.00  60.00   25
  5  \w     91.00 118.00   1.00    4.71    --   92.50 -45.00-150.00   27
  6  \w     56.00 161.00   1.00    4.71    --   92.50  15.00 -30.00  105
  7  \w     30.00  59.00   1.00    4.71    --   92.50 -94.00-180.00   29
  8  \w     80.00 163.00   1.00    4.71    --   92.50  77.00-150.00   83
  9  \w     76.00 117.00   1.00    4.71    --   92.50 125.00 -60.00   41
 10  \w     26.00  51.00   1.00    4.71    --   92.50 -45.00-150.00   25
 11  \w     12.00  38.00   1.00    4.71    --   92.50 -94.00 120.00   26
 12  \w    144.00 169.00   1.00    4.71    --   92.50  77.00-120.00   25
 13  \w     64.00 104.00   1.00    4.71    --   92.50  61.00  30.00   40
 14  \w     34.00  74.00   1.00    4.71    --   92.50 -94.00 -60.00   40
 15  \w     75.00 115.00   1.00    4.71    --   92.50 -45.00  30.00   40
 16  \w     25.00  73.00   1.00    4.71    --   92.50 -45.00  30.00   48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0276380000
_diffrn_orient_matrix_UB_12      0.0076751000
_diffrn_orient_matrix_UB_13      0.1246974000
_diffrn_orient_matrix_UB_21      -0.1281079000
_diffrn_orient_matrix_UB_22      0.1743936000
_diffrn_orient_matrix_UB_23      -0.0540925000
_diffrn_orient_matrix_UB_31      -0.1300892000
_diffrn_orient_matrix_UB_32      -0.1735569000
_diffrn_orient_matrix_UB_33      -0.0493209000
_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  0.0406
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2880
_diffrn_reflns_point_group_measured_fraction_full 0.795
_diffrn_reflns_point_group_measured_fraction_max 0.795
_diffrn_reflns_theta_full        66.760
_diffrn_reflns_theta_max         66.760
_diffrn_reflns_theta_min         4.148
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.597
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.133
_exptl_crystal_description       block
_exptl_crystal_F_000             220
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.104
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 389 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1697
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.928
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0429
_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          0.1183
_refine_ls_wR_factor_ref         0.1383
_reflns_Friedel_coverage         0.453
_reflns_Friedel_fraction_full    0.550
_reflns_Friedel_fraction_max     0.550
_reflns_number_gt                1336
_reflns_number_total             1697
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc02421h2.cif
_cod_data_source_block           s1223-1_auto
_cod_depositor_comments          'Adding full bibliography for 1574638.cif.'
_cod_database_code               1574638
_shelx_shelxl_version_number     2019/1
_chemical_oxdiff_formula         'C H O'
_shelx_estimated_absorpt_t_max   0.943
_shelx_estimated_absorpt_t_min   0.926
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C2(H2), C3(H3), C9(H9)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C12(H12A,H12B,H12C), C11(H11A,H11B,H11C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 1.549
_oxdiff_exptl_absorpt_empirical_full_min 0.779