Palladium-catalyzed asymmetric propargylic sulfonylation of propargyl esters with sulfonyl hydrazides.
Ou, Zhi-Xiong; Zhang, Bu-Hong; Song, Jia-Xin; Li, Li-Bo; Wang, Xing-Wang; Organic & biomolecular chemistry 23 (2025) 10479–10487; doi:10.1039/d5ob01408e

data_7160817
_publ_section_title
;
 Palladium-catalyzed asymmetric propargylic sulfonylation of propargyl
 esters with sulfonyl hydrazides.
;
_journal_issue                   46
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10479
_journal_page_last               10487
_journal_paper_doi               10.1039/d5ob01408e
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration unk
_chemical_formula_sum            'C25 H32 O2 S'
_chemical_formula_weight         396.56
_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-2018/3
_audit_update_record
;
2025-01-15 deposited with the CCDC.	2025-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6368(2)
_cell_length_b                   11.6180(3)
_cell_length_c                   22.8872(6)
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      27.4626
_cell_measurement_theta_min      2.6698
_cell_volume                     2296.56(10)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      220(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            24205
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         1.966
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1811 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.878
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         5215
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.878
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0381
_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^+0.3131P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1234
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                4694
_reflns_number_total             5215
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01408e2.cif
_cod_data_source_block           b250109c_a
_cod_depositor_comments          'Adding full bibliography for 7160817.cif.'
_cod_database_code               7160817
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.940
_shelx_estimated_absorpt_t_max   0.994
_shelx_res_checksum              53401