Enantioconvergent Copper Catalysis: In Situ Generation of the Chiral Phosphorus Ylide and Its Wittig Reactions.
Zhang, Kai; Lu, Liang-Qiu; Yao, Sheng; Chen, Jia-Rong; Shi, De-Qing; Xiao, Wen-Jing; Journal of the American Chemical Society 139 (2017) 12847–12854; doi:10.1021/jacs.7b08207

data_4131657
_publ_section_title
;
 Enantioconvergent Copper Catalysis: In Situ Generation of the Chiral
 Phosphorus Ylide and Its Wittig Reactions.
;
_journal_issue                   36
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12847
_journal_page_last               12854
_journal_paper_doi               10.1021/jacs.7b08207
_journal_volume                  139
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C18 H20 O4'
_chemical_formula_weight         300.34
_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
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 92.7030(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.7010(2)
_cell_length_b                   5.65890(10)
_cell_length_c                   18.6740(4)
_cell_measurement_reflns_used    4893
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      69.82
_cell_measurement_theta_min      4.74
_cell_volume                     812.89(3)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0803
_diffrn_reflns_av_unetI/netI     0.0860
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11508
_diffrn_reflns_point_group_measured_fraction_full 0.929
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.895
_diffrn_reflns_theta_min         2.369
_exptl_absorpt_coefficient_mu    0.701
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details
; 
 Flack x determined using 1028 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.04(2)
_refine_ls_extinction_coef       0.049(8)
_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   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2771
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0700
_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^)+(0.1260P)^2^+0.0495P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1700
_refine_ls_wR_factor_ref         0.1723
_reflns_Friedel_coverage         0.704
_reflns_Friedel_fraction_full    0.863
_reflns_Friedel_fraction_max     0.862
_reflns_number_gt                2655
_reflns_number_total             2771
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b08207_si_004.cif
_cod_data_source_block           cu_170314d_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4131657
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.896
_shelx_estimated_absorpt_t_max   0.966
_shelx_res_checksum              64875
_shelx_hkl_checksum              25406