TADDOL-based <i>P</i>,<i>S</i>-bidentate phosphoramidite ligands in palladium-catalyzed asymmetric allylic substitution.
Gavrilov, Konstantin N.; Chuchelkin, Ilya V.; Firsin, Ilya D.; Trunina, Valeria M.; Gavrilov, Vladislav K.; Zheglov, Sergey V.; Fedorov, Denis A.; Tafeenko, Victor A.; Zamilatskov, Ilya A.; Zimarev, Vladislav S.; Goulioukina, Nataliya S.; Organic & biomolecular chemistry 22 (2024) 538–549; doi:10.1039/d3ob01891a

data_7159710
_publ_section_title
;
 TADDOL-based <i>P</i>,<i>S</i>-bidentate phosphoramidite ligands in
 palladium-catalyzed asymmetric allylic substitution.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              538
_journal_page_last               549
_journal_paper_doi               10.1039/d3ob01891a
_journal_volume                  22
_journal_year                    2024
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C38 H44 N O4 P S'
_chemical_formula_sum            'C38 H44 N O4 P S'
_chemical_formula_weight         641.77
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2022-10-19 deposited with the CCDC.	2023-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                82.188(2)
_cell_angle_beta                 80.662(2)
_cell_angle_gamma                60.1160(10)
_cell_formula_units_Z            2
_cell_length_a                   9.4004(2)
_cell_length_b                   9.4572(2)
_cell_length_c                   22.4551(4)
_cell_measurement_reflns_used    30223
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      68.12
_cell_measurement_theta_min      4.00
_cell_volume                     1704.38(6)
_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 0.984
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  STOE
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            34079
_diffrn_reflns_point_group_measured_fraction_full 0.690
_diffrn_reflns_point_group_measured_fraction_max 0.688
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         67.943
_diffrn_reflns_theta_min         1.998
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.606
_exptl_absorpt_correction_T_max  0.606
_exptl_absorpt_correction_T_min  0.411
_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    1.251
_exptl_crystal_description       block
_exptl_crystal_F_000             684
_exptl_crystal_size_max          .32
_exptl_crystal_size_mid          .24
_exptl_crystal_size_min          .16
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details
;
 Flack x determined using 2108 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(16)
_refine_ls_extinction_coef       0.0052(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     824
_refine_ls_number_reflns         8542
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0477
_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^)+(0.0937P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1272
_reflns_Friedel_coverage         0.446
_reflns_Friedel_fraction_full    0.426
_reflns_Friedel_fraction_max     0.424
_reflns_number_gt                7448
_reflns_number_total             8542
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01891a2.cif
_cod_data_source_block           gavr64
_cod_depositor_comments
;
Adding full bibliography for 7159710--7159711.cif.

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C76 H88 N2 O8 P2 S2'
_cod_original_formula_weight         1283.54
_cod_original_formula_moiety         '2(C38 H44 N O4 P S)'
_cod_original_formula_units_Z            1
_cod_database_code               7159710
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              11624