Rhodium-catalyzed enantioselective hydrogenation of (1-arylvinyl)phosphonates with TADDOL-based phosphoramidite P,S ligands.
Zimarev, Vladislav S.; Firsin, Ilya D.; Larin, Alexander V.; Tafeenko, Victor A.; Bondarenko, Grigoriy N.; Chuchelkin, Ilya V.; Gavrilov, Vladislav K.; Gavrilov, Konstantin N.; Goulioukina, Nataliya S.; Beletskaya, Irina P.; Organic & biomolecular chemistry 23 (2025) 5600–5610; doi:10.1039/d5ob00602c

data_7160543
_publ_section_title
;
 Rhodium-catalyzed enantioselective hydrogenation of
 (1-arylvinyl)phosphonates with TADDOL-based phosphoramidite P,S ligands.
;
_journal_issue                   23
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5600
_journal_page_last               5610
_journal_paper_doi               10.1039/d5ob00602c
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C51 H55 B Cl9 F4 N O4 P Rh S'
_chemical_formula_sum            'C51 H55 B Cl9 F4 N O4 P Rh S'
_chemical_formula_weight         1317.76
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2025-01-31 deposited with the CCDC.	2025-05-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.8778(8)
_cell_length_b                   16.9391(8)
_cell_length_c                   20.3030(7)
_cell_measurement_reflns_used    5844
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      22.85
_cell_measurement_theta_min      1.92
_cell_volume                     5804.5(4)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      295
_diffrn_detector                 Pilatus100K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  stoe
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1356
_diffrn_reflns_av_unetI/netI     0.3304
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            80977
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         28.633
_diffrn_reflns_theta_min         2.405
_diffrn_source                   'Mo LFF Sealed Tube'
_diffrn_source_current           40
_diffrn_source_power             2.000
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.828
_exptl_absorpt_correction_T_max  0.739
_exptl_absorpt_correction_T_min  0.457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_description       block
_exptl_crystal_F_000             2680
_exptl_crystal_size_max          .29
_exptl_crystal_size_mid          .23
_exptl_crystal_size_min          .21
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Flack x determined using 1272 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.770
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     657
_refine_ls_number_reflns         14049
_refine_ls_number_restraints     34
_refine_ls_restrained_S_all      0.781
_refine_ls_R_factor_all          0.2525
_refine_ls_R_factor_gt           0.0591
_refine_ls_shift/su_max          0.036
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0439P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1450
_reflns_Friedel_coverage         0.804
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.924
_reflns_number_gt                4153
_reflns_number_total             14049
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00602c2.cif
_cod_data_source_block           gavr75
_cod_depositor_comments
'Adding full bibliography for 7160541--7160543.cif.'
_cod_database_code               7160543
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              22999