ModularP-Chirogenic Phosphine-Sulfide Ligands: Clear Evidence for Both Electronic Effect andP-Chirality Driving Enantioselectivity in Palladium-Catalyzed Allylations
Bayardon, Jérôme; Maronnat, Milène; Langlois, Adam; Rousselin, Yoann; Harvey, Pierre D.; Jugé, Sylvain; Organometallics 34 (2015) 4340–; doi:10.1021/acs.organomet.5b00585

data_4087763
_publ_section_title
;
 ModularP-Chirogenic Phosphine-Sulfide Ligands: Clear Evidence for Both
 Electronic Effect andP-Chirality Driving Enantioselectivity in
 Palladium-Catalyzed Allylations
;
_journal_issue                   17
_journal_name_full               Organometallics
_journal_page_first              4340
_journal_paper_doi               10.1021/acs.organomet.5b00585
_journal_volume                  34
_journal_year                    2015
_chemical_formula_moiety         'C22 H23 O P S'
_chemical_formula_sum            'C22 H23 O P S'
_chemical_formula_weight         366.43
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2013-10-24
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_audit_update_record
;
2013-10-24 # Formatted by publCIF
;
_cell_angle_alpha                90
_cell_angle_beta                 101.153(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9198(3)
_cell_length_b                   12.7426(5)
_cell_length_c                   17.1748(6)
_cell_measurement_temperature    115
_cell_volume                     1915.25(12)
_computing_cell_refinement
;
Bruker (2013). <i>SAINT</i>. Bruker AXS Inc., Madison, Wisconsin, USA.
;
_computing_data_collection
;
Bruker (2013). <i>APEX2</i>.Bruker AXS Inc., Madison, Wisconsin, USA.
;
_computing_data_reduction
;
Bruker (2013). <i>SAINT</i>. Bruker AXS Inc., Madison, Wisconsin, USA.
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      115.0
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean 9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Nonius Kappa APEX II'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a~1~'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0768
_diffrn_reflns_av_unetI/netI     0.0722
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            71788
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.303
_diffrn_reflns_theta_min         2.823
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2012/1 (Bruker,2012)'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_recrystallization_method
'The material was recrystallised from ether by slow evaporation'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.01(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    2
_refine_ls_number_parameters     460
_refine_ls_number_reflns         15619
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0482
_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^)+(0.0514P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1063
_reflns_Friedel_coverage         0.929
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                12163
_reflns_number_total             15619
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om5b00585_si_001.cif
_cod_data_source_block           12jb890
_cod_original_cell_volume        1915.24(12)
_cod_database_code               4087763
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.926
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 S1A-C20A \\sim S1B-C20A
 with sigma of 0.02
 S1A-C21A \\sim S1B-C21A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(S1A) = Uanis(S1B)
4. Others
 Sof(S1B)=Sof(H20C)=Sof(H20D)=Sof(H21C)=Sof(H21D)=1-FVAR(1)
 Sof(S1A)=Sof(H20A)=Sof(H20B)=Sof(H21A)=Sof(H21B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C20(H20E,H20F), C21(H21E,H21F), C20A(H20A,H20B), C20A(H20C,H20D), C21A(H21A,
 H21B), C21A(H21C,H21D)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C17(H17), C18(H18), C19(H19), C3A(H3A), C4A(H4A), C5A(H5A),
  C6A(H6A), C9A(H9A), C10A(H10A), C11A(H11A), C12A(H12A), C13A(H13A),
 C14A(H14A), C17A(H17A), C18A(H18A), C19A(H19A)
5.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C22(H22D,H22E,H22F), C1A(H1AA,H1AB,H1AC), C22A(H22A,H22B,H22C)
;
_shelx_res_checksum              99087
_shelx_hkl_checksum              45369