Synthesis of Tetrahydro[1,3,4]triazepines via Redox-Neutral α-C(sp<sup>3</sup>)-H Amination of Cyclic Amines.
An, Xiao-De; Duan, Kang; Li, Xian-Jiang; Yang, Jian-Ming; Lu, Yong-Na; Liu, Qing; Xiao, Jian; The Journal of organic chemistry 84 (2019) 11839–11847; doi:10.1021/acs.joc.9b01703

data_4034497
_publ_section_title
;
 Synthesis of Tetrahydro[1,3,4]triazepines via Redox-Neutral
 \a-C(sp<sup>3</sup>)-H Amination of Cyclic Amines.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11839
_journal_page_last               11847
_journal_paper_doi               10.1021/acs.joc.9b01703
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C23 H23 N3'
_chemical_formula_weight         341.44
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_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 92.215(8)
_cell_angle_gamma                90
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_cell_length_a                   9.3516(8)
_cell_length_b                   13.4322(12)
_cell_length_c                   16.9369(13)
_cell_measurement_reflns_used    1467
_cell_measurement_temperature    293(2)
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_cell_measurement_theta_min      5.2310
_cell_volume                     2125.9(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
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_diffrn_ambient_temperature      293(2)
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_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
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_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -10
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_diffrn_reflns_theta_full        67.249
_diffrn_reflns_theta_max         67.249
_diffrn_reflns_theta_min         5.227
_diffrn_source                   'fine-focus sealed X-ray tube'
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_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78003
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            WHITE
_exptl_crystal_density_diffrn    1.067
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.134
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_refine_ls_extinction_coef       0.0022(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3792
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.716
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0537
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1660
_refine_ls_wR_factor_ref         0.2399
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2006
_reflns_number_total             3792
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01703_si_003.cif
_cod_data_source_block           exp_9712_sq
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4034497
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.944
_shelx_estimated_absorpt_t_max   0.948
_shelx_res_checksum              97570
_shelx_hkl_checksum              66123
_shelx_fab_checksum              50688