Metal- and Reagent-Free Intramolecular Oxidative Amination of Tri- and Tetrasubstituted Alkenes.
Xiong, Peng; Xu, He-Huan; Xu, Hai-Chao; Journal of the American Chemical Society 139 (2017) 2956–2959; doi:10.1021/jacs.7b01016

data_4125533
_publ_section_title
;
 Metal- and Reagent-Free Intramolecular Oxidative Amination of Tri- and
 Tetrasubstituted Alkenes.
;
_journal_issue                   8
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2956
_journal_page_last               2959
_journal_paper_doi               10.1021/jacs.7b01016
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C22 H25 N O3'
_chemical_formula_sum            'C22 H25 N O3'
_chemical_formula_weight         351.43
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-01-07
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.978(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.193(2)
_cell_length_b                   7.1614(13)
_cell_length_c                   23.653(4)
_cell_measurement_reflns_used    6203
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      28.00
_cell_measurement_theta_min      2.84
_cell_volume                     1872.7(6)
_computing_cell_refinement       'SAINT v6.28A (Bruker, 2002)'
_computing_data_reduction        'SAINT v6.28A (Bruker, 2002)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            15915
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.863
_diffrn_reflns_theta_min         1.743
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.905135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS v.2.03 (Bruker,200?) was used for absorption correction.
R(int) was 0.0513 before and 0.0337 after correction.
The Ratio of minimum to maximum transmission is 0.9051.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4546
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.941
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0476
_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^)+(0.0790P)^2^+0.5210P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1246
_refine_ls_wR_factor_ref         0.1305
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3877
_reflns_number_total             4546
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b01016_si_002.cif
_cod_data_source_block           xu01052m
_cod_depositor_comments          'Adding full bibliography for 4125533.cif.'
_cod_original_cell_volume        1872.6(6)
_cod_database_code               4125533
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C22(H22), C18(H18), C21(H21), C12(H12), C15(H15), C11(H11),
 C14(H14), C13(H13)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C4(H4A,H4B,H4C), C20(H20A,H20B,H20C), C5(H5A,H5B,H5C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'