Palladium-catalyzed asymmetric 1,6-addition of diarylphosphines to alpha,beta,gamma,delta-unsaturated sulfonic esters: controlling regioselectivity by rational selection of electron-withdrawing groups
Junzhu Lu; Jinxing Ye; Wei-Liang Duan; Chem.Commun. 50 (2014) 698–; doi:10.1039/c3cc46290k

data_7110232
_publ_section_title
;
 Palladium-catalyzed asymmetric 1,6-addition of diarylphosphines to
 alpha,beta,gamma,delta-unsaturated sulfonic esters: controlling
 regioselectivity by rational selection of electron-withdrawing groups
;
_journal_name_full               Chem.Commun.
_journal_page_first              698
_journal_paper_doi               10.1039/c3cc46290k
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C25 H24 F3 O4 P S'
_chemical_formula_weight         508.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 99.518(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.6851(12)
_cell_length_b                   16.633(4)
_cell_length_c                   13.304(3)
_cell_measurement_reflns_used    2424
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      24.79
_cell_measurement_theta_min      2.45
_cell_volume                     1240.7(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      140(2)
_diffrn_measured_fraction_theta_full 1.000
_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  0.0457
_diffrn_reflns_av_unetI/netI     0.0781
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12282
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.606
_diffrn_reflns_theta_min         1.552
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
; 
 Flack x determined using 2068 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.06(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         6964
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0513
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0540P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1236
_reflns_Friedel_coverage         0.789
_reflns_Friedel_fraction_full    0.924
_reflns_Friedel_fraction_max     0.833
_reflns_number_gt                5607
_reflns_number_total             6964
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c3cc46290k.txt
_cod_data_source_block           mo_dm13397_0m
_cod_original_cell_volume        1240.7(4)
_cod_database_code               7110232
_shelx_estimated_absorpt_t_min   0.910
_shelx_estimated_absorpt_t_max   0.976
_shelxl_version_number           2013-4
_shelx_res_checksum              21888
_shelx_hkl_checksum              72173