Stereoinversion in Pd-catalyzed allylic substitution induced by modification of olefinic moiety in chiral phosphine-acrylamide ligands.
Watanabe, Kohei; Toba, Yuto; Mita, Shimpei; Kanda, Yusuke; Yagi, Toru; Kanauchi, Kento; Kumada, Manami; Yoshida, Yasushi; Kasashima, Yoshio; Takita, Ryo; Sakamoto, Masami; Mino, Takashi; Organic & biomolecular chemistry 23 (2025) 7431–7438; doi:10.1039/d5ob01034a

data_7160642
_publ_section_title
;
 Stereoinversion in Pd-catalyzed allylic substitution induced by
 modification of olefinic moiety in chiral phosphine-acrylamide ligands.
;
_journal_issue                   32
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7431
_journal_page_last               7438
_journal_paper_doi               10.1039/d5ob01034a
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_sum            'C36 H32 N O P'
_chemical_formula_weight         525.59
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc28cy6t
_audit_update_record
;
2021-07-16 deposited with the CCDC.	2025-07-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.631(3)
_cell_length_b                   11.371(4)
_cell_length_c                   29.685(11)
_cell_measurement_reflns_used    1587
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      18.4213
_cell_measurement_theta_min      2.2562
_cell_volume                     2913.4(18)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0811
_diffrn_reflns_av_unetI/netI     0.1242
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            16838
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.736
_diffrn_reflns_theta_min         1.372
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.592
_refine_ls_abs_structure_details
;
Flack x determined using 1049 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     410
_refine_ls_number_reflns         6641
_refine_ls_number_restraints     508
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.1559
_refine_ls_R_factor_gt           0.0846
_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^)+(0.0997P)^2^+1.4536P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1943
_refine_ls_wR_factor_ref         0.2330
_reflns_number_gt                3660
_reflns_number_total             6641
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01034a2.cif
_cod_data_source_block           I_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7160641--7160643.cif.'
_cod_original_cell_volume        2913.4(19)
_cod_database_code               7160642