Stereospecific Cross Couplings To Set Benzylic, All-Carbon Quaternary Stereocenters in High Enantiopurity.
Zhou, Qi; Cobb, Kelsey M.; Tan, Tianyu; Watson, Mary P.; Journal of the American Chemical Society 138 (2016) 12057–12060; doi:10.1021/jacs.6b08075

data_4125229
_publ_section_title
;
 Stereospecific Cross Couplings To Set Benzylic, All-Carbon Quaternary
 Stereocenters in High Enantiopurity.
;
_journal_issue                   37
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12057
_journal_page_last               12060
_journal_paper_doi               10.1021/jacs.6b08075
_journal_volume                  138
_journal_year                    2016
_chemical_absolute_configuration 1
_chemical_formula_sum            'C16 H18 O2'
_chemical_formula_weight         242.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 97.282(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.7695(7)
_cell_length_b                   5.8807(2)
_cell_length_c                   10.4637(3)
_cell_measurement_reflns_used    9838
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      74.89
_cell_measurement_theta_min      4.09
_cell_volume                     1328.76(7)
_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      200(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker AXS APEX diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13728
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         75.069
_diffrn_reflns_theta_min         4.094
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_T_max  0.7539
_exptl_absorpt_correction_T_min  0.6441
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX3 (Bruker, 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_description       clear
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.269
_exptl_crystal_size_mid          0.196
_exptl_crystal_size_min          0.144
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
; 
 Flack x determined using 1141 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.15(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2708
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0349
_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^)+(0.0638P)^2^+0.1971P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.0948
_reflns_Friedel_coverage         0.808
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                2626
_reflns_number_total             2708
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b08075_si_003.cif
_cod_data_source_block           mary035
_cod_depositor_comments
'Adding full bibliography for 4125228--4125229.cif.'
_cod_database_code               4125229
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.851
_shelx_estimated_absorpt_t_max   0.916
_shelx_res_checksum              15046
_shelx_hkl_checksum              81563