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_7160541
_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         'C8 H10 Cl O3 P'
_chemical_formula_sum            'C8 H10 Cl O3 P'
_chemical_formula_weight         220.58
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc2d3jbd
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2022-09-17 deposited with the CCDC.	2025-05-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.618(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.5220(10)
_cell_length_b                   5.6987(4)
_cell_length_c                   26.800(3)
_cell_measurement_reflns_used    4242
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.85
_cell_measurement_theta_min      2.52
_cell_volume                     2362.9(3)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      295
_diffrn_detector                 Pilatus100K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_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  0.0968
_diffrn_reflns_av_unetI/netI     0.4808
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            16165
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.351
_diffrn_reflns_theta_min         2.546
_diffrn_source                   'Mo LFF Sealed Tube'
_diffrn_source_current           40
_diffrn_source_power             2.000
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.435
_exptl_absorpt_correction_T_max  0.600
_exptl_absorpt_correction_T_min  0.501
_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    1.240
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          .27
_exptl_crystal_size_mid          .21
_exptl_crystal_size_min          .14
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.26(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.866
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         5274
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.866
_refine_ls_R_factor_all          0.2280
_refine_ls_R_factor_gt           0.0442
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[\s^2^(Fo^2^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0736
_refine_ls_wR_factor_ref         0.0988
_reflns_Friedel_coverage         0.823
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                1118
_reflns_number_total             5274
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00602c2.cif
_cod_data_source_block           gavr71
_cod_depositor_comments
'Adding full bibliography for 7160541--7160543.cif.'
_cod_original_sg_symbol_H-M      'I 2'
_cod_database_code               7160541
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              49056