Bu<sub>4</sub>NI-Catalyzed, Radical-Induced Regioselective <i>N</i>-Alkylations and Arylations of Tetrazoles Using Organic Peroxides/Peresters.
Rajamanickam, Suresh; Sah, Chitranjan; Mir, Bilal Ahmad; Ghosh, Subhendu; Sethi, Garima; Yadav, Vinita; Venkataramani, Sugumar; Patel, Bhisma K.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b02875

data_4037843
_publ_section_title
;
 Bu<sub>4</sub>NI-Catalyzed, Radical-Induced Regioselective
 <i>N</i>-Alkylations and Arylations of Tetrazoles Using Organic
 Peroxides/Peresters.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02875
_journal_year                    2020
_chemical_formula_sum            'C13 H9 Br N4'
_chemical_formula_weight         301.15
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.670(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.253(3)
_cell_length_b                   11.145(3)
_cell_length_c                   10.015(2)
_cell_measurement_reflns_used    4765
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      19.90
_cell_measurement_theta_min      2.58
_cell_volume                     1247.5(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0567
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16641
_diffrn_reflns_theta_full        24.31
_diffrn_reflns_theta_max         24.31
_diffrn_reflns_theta_min         2.58
_exptl_absorpt_coefficient_mu    3.281
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.416(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.997
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1983
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.996
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0376
_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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0798
_reflns_number_gt                1728
_reflns_number_total             1983
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b02875_si_002.cif
_cod_data_source_block           rss29-09_0m_b
_cod_original_sg_symbol_H-M      Cc
_cod_database_code               4037843