Chemo- and Stereoselective Transition-Metal-Free Amination of Amides with Azides.
Tona, Veronica; de la Torre, Aurélien; Padmanaban, Mohan; Ruider, Stefan; González, Leticia; Maulide, Nuno; Journal of the American Chemical Society 138 (2016) 8348–8351; doi:10.1021/jacs.6b04061

data_4130494
_publ_section_title
;
 Chemo- and Stereoselective Transition-Metal-Free Amination of Amides with
 Azides.
;
_journal_issue                   27
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8348
_journal_page_last               8351
_journal_paper_doi               10.1021/jacs.6b04061
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C19 H27 N2 O2, C F3 O3 S, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C20.5 H28 Cl F3 N2 O5 S'
_chemical_formula_weight         506.95
_chemical_name_systematic
;
1-(5-Methoxy-6-phenethyl-8-oxa-6-azabicyclo[3.2.1]
octan-7-ylidene)pyrrolidin-1-ium trifluoromethanesulfonate 
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-04-19
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                67.422(3)
_cell_angle_beta                 72.456(4)
_cell_angle_gamma                78.457(3)
_cell_formula_units_Z            4
_cell_length_a                   12.3584(10)
_cell_length_b                   13.1989(10)
_cell_length_c                   16.1664(12)
_cell_measurement_reflns_used    9839
_cell_measurement_temperature    130.0
_cell_measurement_theta_max      34.377
_cell_measurement_theta_min      2.493
_cell_volume                     2311.0(3)
_computing_cell_refinement       'APEX2 v2011.2-0'
_computing_data_collection       'APEX2 v2011.2-0'
_computing_data_reduction        'APEX2 v2011.2-0'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      130.0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            107115
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.860
_diffrn_reflns_theta_min         2.297
_diffrn_source                   'INCOATEC microfocus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.315
_exptl_absorpt_correction_T_max  0.7470
_exptl_absorpt_correction_T_min  0.6874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction. 
wR2(int) was 0.1210 before and 0.0440 after correction. 
The Ratio of minimum to maximum transmission is 0.9202. 
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_description       plate
_exptl_crystal_F_000             1060
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.124
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     588
_refine_ls_number_reflns         21300
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0550P)^2^+0.5839P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1250
_reflns_Friedel_coverage         0.000
_reflns_number_gt                14936
_reflns_number_total             21300
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b04061_si_001.cif
_cod_data_source_block           veto220_P-1
_cod_depositor_comments
;

2020-08-05
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C19 H27 N2 O2), 2(C F3 O3 S), C H2 Cl2'
_cod_original_formula_sum        'C41 H56 Cl2 F6 N4 O10 S2'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     1013.91
_cod_database_code               4130494
_shelxl_version_number           2013-3
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.934
_shelx_res_checksum              41125
_shelx_hkl_checksum              90496