I2-Mediated Intramolecular C-H Amidation for the Synthesis of N-Substituted Benzimidazoles.
Hu, Zhiyuan; Zhao, Ting; Wang, Manman; Wu, Jie; Yu, Wenquan; Chang, Junbiao; The Journal of organic chemistry 82 (2017) 3152–3158; doi:10.1021/acs.joc.7b00142

data_4032205
_publ_section_title
;
 I2-Mediated Intramolecular C-H Amidation for the Synthesis of
 N-Substituted Benzimidazoles.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3152
_journal_page_last               3158
_journal_paper_doi               10.1021/acs.joc.7b00142
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C23 H22 N2 O2 S'
_chemical_formula_weight         390.49
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 102.181(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.8124(5)
_cell_length_b                   14.2482(6)
_cell_length_c                   12.3794(6)
_cell_measurement_reflns_used    7273
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.60
_cell_volume                     2036.61(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_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      273(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  0.0497
_diffrn_reflns_av_sigmaI/netI    0.0402
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21845
_diffrn_reflns_theta_full        27.57
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  0.9718
_exptl_absorpt_correction_T_min  0.9650
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.567
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.175
_refine_ls_extinction_coef       0.042(4)
_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   1.292
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         4692
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.292
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0592
_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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1599
_refine_ls_wR_factor_ref         0.1822
_reflns_number_gt                3608
_reflns_number_total             4692
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b00142_si_002.cif
_cod_data_source_block           a
_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/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 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4032205.cif.
;
_cod_original_sg_symbol_H-M      'P2(1)/n  '
_cod_database_code               4032205