tert-Butyl peroxide (TBHP)/KI-mediated dual C(sp2)-H bond amination of arylamines with α-diazo carbonyls toward 1,2,4-benzotriazines
Jiang, Bo; Zhang, Tian-Shu; Zhang, Hongping; Fu, Rong; Wang, Jianyi; Hao, Wen-Juan; Tu, Shu-Jiang; Chemical Communications  (2019) –; doi:10.1039/C9CC07236E

data_7124300
_publ_section_title
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 tert-Butyl peroxide (TBHP)/KI-mediated dual C(sp2)-H bond amination of
 arylamines with \a-diazo carbonyls toward 1,2,4-benzotriazines
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC07236E
_journal_year                    2019
_chemical_formula_sum            'C15 H11 N3 O'
_chemical_formula_weight         249.27
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2018-09-17 deposited with the CCDC.    2019-10-11 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.142(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.647(7)
_cell_length_b                   21.749(19)
_cell_length_c                   7.647
_cell_measurement_reflns_used    1117
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.361
_cell_measurement_theta_min      2.824
_cell_volume                     1271.8(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0704
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2226
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.82
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9807
_exptl_absorpt_correction_T_min  0.9667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0007(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2226
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1277
_refine_ls_R_factor_gt           0.0505
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0228P)^2^+0.2513P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.1095
_reflns_number_gt                1124
_reflns_number_total             2226
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9cc07236e2.cif
_cod_data_source_block           150702f
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        1271.9(15)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7124300