Copper(I)-Catalyzed Regioselective Amination of N-Aryl Imines Using TMSN3 and TBHP: A Route to Substituted Benzimidazoles.
Mahesh, Devulapally; Sadhu, Pradeep; Punniyamurthy, Tharmalingam; The Journal of organic chemistry 80 (2015) 1644–1650; doi:10.1021/jo502574u

data_4030595
_publ_section_title
;
 Copper(I)-Catalyzed Regioselective Amination of N-Aryl Imines Using TMSN3
 and TBHP: A Route to Substituted Benzimidazoles.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1644
_journal_page_last               1650
_journal_paper_doi               10.1021/jo502574u
_journal_volume                  80
_journal_year                    2015
_chemical_formula_sum            'C14 H11 Br N2'
_chemical_formula_weight         287.1583
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_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                92.198(2)
_cell_angle_beta                 101.769(2)
_cell_angle_gamma                90.037(2)
_cell_formula_units_Z            4
_cell_length_a                   9.6050(3)
_cell_length_b                   9.8138(3)
_cell_length_c                   13.4980(4)
_cell_measurement_temperature    296(2)
_cell_volume                     1244.63(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_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  0.0413
_diffrn_reflns_av_sigmaI/netI    0.0387
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16299
_diffrn_reflns_theta_full        24.41
_diffrn_reflns_theta_max         24.41
_diffrn_reflns_theta_min         1.54
_exptl_absorpt_coefficient_mu    3.280
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.971
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4003
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0472
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1486
_refine_ls_wR_factor_ref         0.1669
_reflns_number_gt                2726
_reflns_number_total             4003
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo502574u_si_001.cif
_cod_data_source_block           dm-195-2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/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 3008 2015-01-20 13:52:24Z robertas 

 Adding full bibliography for 4030595.cif.
;
_cod_database_code               4030595