Triflic Acid Promoted Decarboxylation of Adamantane-oxazolidine-2-one: Access to Chiral Amines and Heterocycles.
Hrdina, Radim; Larrosa, Marta; Logemann, Christian; The Journal of organic chemistry 82 (2017) 4891–4899; doi:10.1021/acs.joc.7b00711

data_4032441
_publ_section_title
;
 Triflic Acid Promoted Decarboxylation of Adamantane-oxazolidine-2-one:
 Access to Chiral Amines and Heterocycles.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4891
_journal_page_last               4899
_journal_paper_doi               10.1021/acs.joc.7b00711
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration 'R, S'
_chemical_formula_moiety         'C20 H23 N O4'
_chemical_formula_sum            'C20 H23 N O4'
_chemical_formula_weight         341.39
_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   difmap
_atom_sites_solution_primary     'intrinsic phasing'
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 109.077(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.5904(4)
_cell_length_b                   6.8559(3)
_cell_length_c                   12.0499(4)
_cell_measurement_reflns_used    9816
_cell_measurement_temperature    102(2)
_cell_measurement_theta_max      50.06
_cell_measurement_theta_min      3.47
_cell_volume                     826.85(6)
_computing_cell_refinement       'APEX3 v2014.5-2'
_computing_data_collection       'APEX3 v2015.5-2'
_computing_data_reduction        'APEX3 v2014.5-2'
_computing_molecular_graphics    'Diamond 4.3'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      102(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'BRUKER D8 Venture, Bruker Photon 100 CMOS detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            84673
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         44.999
_diffrn_reflns_theta_min         3.118
_diffrn_source                   'ImuS microfocus source'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS-2014/5, Bruker, Madison, 2014'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.439
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.125
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 5073 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         13615
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0383
_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^)+(0.0539P)^2^+0.0322P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0927
_reflns_Friedel_coverage         0.894
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                12017
_reflns_number_total             13615
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00711_si_002.cif
_cod_data_source_block           mo_rhb_69_bl_0m
_cod_depositor_comments          'Adding full bibliography for 4032441.cif.'
_cod_database_code               4032441
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.959
_shelx_estimated_absorpt_t_max   0.988
_shelx_res_checksum              11534
_shelx_hkl_checksum              16073