Oxy-Allyl Cation Catalysis: An Enantioselective Electrophilic Activation Mode.
Liu, Chun; Oblak, E. Zachary; Vander Wal, Mark N.; Dilger, Andrew K.; Almstead, Danielle K.; MacMillan, David W. C.; Journal of the American Chemical Society 138 (2016) 2134–2137; doi:10.1021/jacs.5b13041

data_4130035
_publ_section_title
;
 Oxy-Allyl Cation Catalysis: An Enantioselective Electrophilic Activation
 Mode.
;
_journal_issue                   7
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2134
_journal_page_last               2137
_journal_paper_doi               10.1021/jacs.5b13041
_journal_volume                  138
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C21 H20 Br N O2'
_chemical_formula_weight         398.29
_chemical_name_common            ZO-1-21
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 95.999(9)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.756(3)
_cell_length_b                   5.9048(8)
_cell_length_c                   27.030(3)
_cell_measurement_reflns_used    120
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.6006
_cell_measurement_theta_min      5.5445
_cell_volume                     3612.1(8)
_computing_cell_refinement       'APEX2 v2013.4-1 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service (Bruker AXS Inc.)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_unetI/netI     0.0747
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            37316
_diffrn_reflns_point_group_measured_fraction_full 0.923
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         37.132
_diffrn_reflns_theta_min         3.343
_diffrn_source                   'fine focus tube'
_exptl_absorpt_coefficient_mu    2.290
_exptl_absorpt_correction_T_max  0.83
_exptl_absorpt_correction_T_min  0.63
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_refine_diff_density_max         1.002
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
;
 Flack x determined using 3623 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.867
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         16336
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.867
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0338
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0230P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0634
_refine_ls_wR_factor_ref         0.0666
_reflns_Friedel_coverage         0.652
_reflns_Friedel_fraction_full    0.835
_reflns_Friedel_fraction_max     0.755
_reflns_number_gt                11440
_reflns_number_total             16336
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b13041_si_002.cif
_cod_data_source_block           mo_PDJTL2_0m
_cod_original_sg_symbol_H-M      'I 2'
_cod_database_code               4130035
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              13923
_shelx_hkl_checksum              2854