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_4130493
_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         'C21 H35 N2 O, I'
_chemical_formula_sum            'C21 H35 I N2 O'
_chemical_formula_weight         458.41
_chemical_name_systematic
;
2-(Phenethylamino)-1-(pyrrolidin-1-yl)nonan-1-one
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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                90
_cell_angle_beta                 95.927(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.5248(10)
_cell_length_b                   15.134(3)
_cell_length_c                   26.429(5)
_cell_measurement_reflns_used    9714
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      68.715
_cell_measurement_theta_min      3.361
_cell_volume                     2198.0(7)
_computing_cell_refinement       'APEX2 V2013.6-2'
_computing_data_collection       'APEX2 V2013.6-2'
_computing_data_reduction        'APEX2 V2013.6-2'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0990
_diffrn_reflns_av_unetI/netI     0.0621
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            16730
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.232
_diffrn_reflns_theta_min         3.362
_diffrn_source                   'INCOATEC microfocus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    11.512
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1180 before and 0.0734 after correction.
The Ratio of minimum to maximum transmission is 0.5484.
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    1.385
_exptl_crystal_description       needle
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.291
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.035
_refine_diff_density_max         2.170
_refine_diff_density_min         -1.130
_refine_diff_density_rms         0.180
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3965
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0637
_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^)+(0.0700P)^2^+10.3310P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1567
_refine_ls_wR_factor_ref         0.1595
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3641
_reflns_number_total             3965
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b04061_si_002.cif
_cod_data_source_block           vetomopa497_p21n
_cod_database_code               4130493
_shelxl_version_number           2013-3
_shelx_res_checksum              67730
_shelx_hkl_checksum              24490