Ligand's electronegativity controls the sense of enantioselectivity in BIFOP-X palladium-catalyzed allylic alkylations
Brüllingen, Eric; Neudörfl, Jörg-Martin; Goldfuss, Bernd; New Journal of Chemistry 43 (2019) 15743–; doi:10.1039/C9NJ02798J

data_7058969
_publ_section_title
;
 Ligand's electronegativity controls the sense of enantioselectivity in
 BIFOP-X palladium-catalyzed allylic alkylations
;
_journal_issue                   39
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              15743
_journal_paper_doi               10.1039/C9NJ02798J
_journal_volume                  43
_journal_year                    2019
_chemical_absolute_configuration syn
_chemical_formula_sum            'C34 H46 O4'
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_space_group_crystal_system      orthorhombic
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_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-12-20 deposited with the CCDC.	2019-09-09 downloaded from the CCDC.
;
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_cell_length_b                   14.6289(7)
_cell_length_c                   7.9467(4)
_cell_measurement_reflns_used    13860
_cell_measurement_temperature    100(2)
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_cell_measurement_theta_min      6.050
_cell_volume                     1429.71(12)
_computing_cell_refinement       'Bruker APEX 3'
_computing_data_collection       'Bruker APEX 3'
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_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
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;
SHELXL-2014/7 (Sheldrick, 2014)
SHELXLE (C. B. Huebschle 2016)'
;
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
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_diffrn_radiation_type           CuK\a
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_diffrn_reflns_av_R_equivalents  0.0455
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_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
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_diffrn_reflns_limit_l_min       -9
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_diffrn_reflns_point_group_measured_fraction_full 0.988
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_diffrn_reflns_theta_max         72.192
_diffrn_reflns_theta_min         6.050
_diffrn_source                   'micro focus'
_exptl_absorpt_coefficient_mu    0.602
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
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_exptl_crystal_density_diffrn    1.205
_exptl_crystal_description       prism
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_refine_ls_abs_structure_details
;
 Flack x determined using 1117 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.22(7)
_refine_ls_extinction_coef       0.031(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         2776
_refine_ls_number_restraints     2
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_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^)+(0.0607P)^2^+0.1944P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1014
_reflns_Friedel_coverage         0.709
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                2715
_reflns_number_total             2776
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9nj02798j2.cif
_cod_data_source_block           eb127
_cod_database_code               7058969
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.889
_shelx_estimated_absorpt_t_max   0.889
_shelx_res_checksum              29685