Direct Asymmetric Amination of α-Branched Cyclic Ketones Catalyzed by a Chiral Phosphoric Acid.
Yang, Xiaoyu; Toste, F. Dean; Journal of the American Chemical Society 137 (2015) 3205–3208; doi:10.1021/jacs.5b00229

data_4123474
_publ_section_title
;
 Direct Asymmetric Amination of \a-Branched Cyclic Ketones Catalyzed by a
 Chiral Phosphoric Acid.
;
_journal_issue                   9
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3205
_journal_page_last               3208
_journal_paper_doi               10.1021/jacs.5b00229
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C23 H32 N2 O5'
_chemical_formula_weight         416.52
_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   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 95.063(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.2527(6)
_cell_length_b                   10.1344(6)
_cell_length_c                   11.1386(6)
_cell_measurement_reflns_used    9963
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.21
_cell_measurement_theta_min      3.98
_cell_volume                     1152.84(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  'SHELXL-2014 (Sheldrick,2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21859
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         68.228
_diffrn_reflns_theta_min         3.984
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    0.686
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.7121
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
; 
 Flack x determined using 1847 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4110
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0253
_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^)+(0.0350P)^2^+0.2041P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0649
_refine_ls_wR_factor_ref         0.0651
_reflns_Friedel_coverage         0.839
_reflns_Friedel_fraction_full    0.958
_reflns_Friedel_fraction_max     0.944
_reflns_number_gt                4075
_reflns_number_total             4110
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b00229_si_002.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
     Adding full bibliography for 4123474.cif.

2020-10-10
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum        'C1.77 H2.46 F0 N0.15 O0.38'
_cod_original_formula_units_Z    26
_cod_original_formula_weight     32.04
_cod_database_code               4123474
_shelx_estimated_absorpt_t_min   0.916
_shelx_estimated_absorpt_t_max   0.980
_shelxl_version_number           2014-1
_shelx_res_checksum              45142
_shelx_hkl_checksum              46518