Amphiphilic π-Allyliridium C,O-Benzoates Enable Regio- and Enantioselective Amination of Branched Allylic Acetates Bearing Linear Alkyl Groups
Meza, Arismel Tena; Wurm, Thomas; Smith, Lewis; Kim, Seung Wook; Zbieg, Jason R.; Stivala, Craig E.; Krische, Michael J.; Journal of the American Chemical Society  (2018) –; doi:10.1021/jacs.7b13482

data_4127055
_publ_section_title
;
 Amphiphilic \p-Allyliridium C,O-Benzoates Enable Regio- and
 Enantioselective Amination of Branched Allylic Acetates Bearing Linear
 Alkyl Groups
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b13482
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H18 N 1+, Cl 1-'
_chemical_formula_sum            'C13 H18 Cl N'
_chemical_formula_weight         223.73
_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-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 109.866(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.993(2)
_cell_length_b                   9.035(3)
_cell_length_c                   13.737(4)
_cell_measurement_reflns_used    21815
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     1283.2(6)
_computing_cell_refinement
'CrysAlisPro V 1.171.38.46, Agilent Technologies'
_computing_data_collection
'CrysAlisPro V 1.171.38.46, Agilent Technologies'
_computing_data_reduction
'CrysAlisPro V 1.171.38.46, Agilent Technologies'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'Shelxl-2016/6, Sheldrick, G. M.'
_computing_structure_refinement  'Shelxl-2016/6, Sheldrick, G. M.'
_computing_structure_solution
;

SHELXT. Sheldrick, G. M. (2015). Acta Cryst. A71, 3-8. 
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku AFC-12 with Saturn 724+ CCD'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21792
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         3.056
_diffrn_source                   'sealed fine focus tube'
_exptl_absorpt_coefficient_mu    0.268
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Abscor. T. Higashi (2001). The Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.510
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.00(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         5883
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0451
_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^)+(0.0547P)^2^+0.4832P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1108
_refine_ls_wR_factor_ref         0.1160
_reflns_Friedel_coverage         0.881
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                5147
_reflns_number_total             5883
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b13482_si_002.cif
_cod_data_source_block           shelx
_cod_database_code               4127055
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.876
_shelx_estimated_absorpt_t_max   0.992
_shelx_res_checksum              69077
_shelx_hkl_checksum              62857