Enantioselective Cu-catalyzed 1,4-additions of organozinc and Grignard reagents to enones: exceptional performance of the hydrido-phosphite-ligand BIFOP-H
Brüllingen, Eric; Neudörfl, Jörg-Martin; Goldfuss, Bernd; New Journal of Chemistry 43 (2019) 4787–; doi:10.1039/C8NJ05886E

data_7058205
_publ_section_title
;
 Enantioselective Cu-catalyzed 1,4-additions of organozinc and Grignard
 reagents to enones: exceptional performance of the
 hydrido-phosphite-ligand BIFOP-H
;
_journal_issue                   12
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              4787
_journal_paper_doi               10.1039/C8NJ05886E
_journal_volume                  43
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C64 H82 Cl2 Cu2 O4 P2, C10 H18 [+ C10 H18]'
_chemical_formula_sum            'C84 H118 Cl2 Cu2 O4 P2'
_chemical_formula_weight         1451.70
_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   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-08-20 deposited with the CCDC.    2019-02-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.221(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.1193(16)
_cell_length_b                   31.626(4)
_cell_length_c                   15.4815(17)
_cell_measurement_reflns_used    8864
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.31
_cell_measurement_theta_min      3.24
_cell_volume                     7402.6(15)
_computing_cell_refinement       'Bruker APEX 3'
_computing_data_collection       'Bruker APEX 3'
_computing_data_reduction        'Bruker APEX 3'
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2015)'
_computing_structure_refinement
;
SHELXL-2014/7 (Sheldrick, 2014)
SHELXLE (C. B. Huebschle 2016)'
;
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'phi / omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.915
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            80865
_diffrn_reflns_point_group_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.887
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         75.926
_diffrn_reflns_theta_min         2.854
_diffrn_source                   'micro focus'
_exptl_absorpt_coefficient_mu    2.163
_exptl_absorpt_correction_T_max  0.3239
_exptl_absorpt_correction_T_min  0.1972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             3104
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.662
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details
;
 Flack x determined using 9105 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.095(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1553
_refine_ls_number_reflns         27388
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0698
_refine_ls_shift/su_max          0.038
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0791P)^2^+12.8280P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1781
_refine_ls_wR_factor_ref         0.1878
_reflns_Friedel_coverage         0.902
_reflns_Friedel_fraction_full    0.919
_reflns_Friedel_fraction_max     0.857
_reflns_number_gt                23050
_reflns_number_total             27388
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8nj05886e2.cif
_cod_data_source_block           eb214_neu3_sq
_cod_depositor_comments          'Adding full bibliography for 7058205.cif.'
_cod_database_code               7058205
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.672
_shelx_estimated_absorpt_t_max   0.958
_shelx_res_checksum              64125
_shelx_fab_checksum              92239