A Regio- and Enantioselective CuH-Catalyzed Ketone Allylation with Terminal Allenes.
Tsai, Erica Y.; Liu, Richard Y.; Yang, Yang; Buchwald, Stephen L.; Journal of the American Chemical Society 140 (2018) 2007–2011; doi:10.1021/jacs.7b12271

data_4131884
_publ_section_title
;
 A Regio- and Enantioselective CuH-Catalyzed Ketone Allylation with
 Terminal Allenes.
;
_journal_issue                   6
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2007
_journal_page_last               2011
_journal_paper_doi               10.1021/jacs.7b12271
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H30 O4'
_chemical_formula_weight         334.44
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 96.821(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.1913(8)
_cell_length_b                   8.7775(10)
_cell_length_c                   17.654(2)
_cell_measurement_reflns_used    7545
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.18
_cell_measurement_theta_min      2.52
_cell_volume                     952.6(2)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2015)'
_computing_data_collection       'APEX2 v2011.4.0 (Bruker-AXS, 2015)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Smart APEX2 CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9224
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        66.575
_diffrn_reflns_theta_max         66.575
_diffrn_reflns_theta_min         2.521
_diffrn_source
'I\mS micro-focus sealed tube, multilayer optics'
_exptl_absorpt_coefficient_mu    0.637
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6506
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blade
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
; 
 Flack x determined using 1381 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.10(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         3259
_refine_ls_number_restraints     401
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0350
_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^)+(0.0649P)^2^+0.0614P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.0952
_reflns_Friedel_coverage         0.813
_reflns_Friedel_fraction_full    0.935
_reflns_Friedel_fraction_max     0.935
_reflns_number_gt                3159
_reflns_number_total             3259
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b12271_si_004.cif
_cod_data_source_block           X17128
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4131884
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.817
_shelx_estimated_absorpt_t_max   0.954
_shelx_res_checksum              95151
_shelx_hkl_checksum              44806