Direct cleavage of the NN bond of azobenzenes by MeOTf leading to N-arylbenzimidazoles
Yan, Xiaoyu; Yi, Xiangli; Xi, Chanjuan; Org. Chem. Front. 1 (2014) 657–; doi:10.1039/C4QO00056K

data_1552979
_publ_section_title
;
 Direct cleavage of the N&#xE001;N bond of azobenzenes by MeOTf leading to
 N-arylbenzimidazoles
;
_journal_issue                   6
_journal_name_full               'Org. Chem. Front.'
_journal_page_first              657
_journal_paper_doi               10.1039/C4QO00056K
_journal_volume                  1
_journal_year                    2014
_chemical_formula_sum            'C17 H17 F3 N2 O3 S'
_chemical_formula_weight         386.39
_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_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
_cell_angle_alpha                90.00
_cell_angle_beta                 112.99(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.555(3)
_cell_length_b                   8.9872(18)
_cell_length_c                   15.716(3)
_cell_measurement_reflns_used    4983
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      1.63
_cell_volume                     1762.5(7)
_computing_cell_refinement       'Siemens SMART & SAINT'
_computing_data_collection       'Siemens SMART'
_computing_data_reduction        'Siemens XPREP'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Siemens SHELXTL'
_computing_structure_solution    'Siemens SHELXTL'
_diffrn_ambient_temperature      173.1500
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w 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  0.0402
_diffrn_reflns_av_sigmaI/netI    0.0356
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12272
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.63
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  .920
_exptl_absorpt_correction_T_min  .884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          .633
_exptl_crystal_size_mid          .441
_exptl_crystal_size_min          .357
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.162
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4033
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.171
_refine_ls_R_factor_gt           0.0593
_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^)+(0.0803P)^2^+0.8634P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1576
_refine_ls_wR_factor_ref         0.1672
_reflns_number_gt                3758
_reflns_number_total             4033
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4qo00056k2.cif
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        1762.6(6)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1552979
_refine_ls_r_factor_ref          0.0659