Accessing Benzimidazoles via a Ring Distortion Strategy: An Oxone Mediated Tandem Reaction of 2-Aminobenzylamines.
Hati, Santanu; Kumar Dutta, Pratip; Dutta, Sanjay; Munshi, Parthapratim; Sen, Subhabrata; Organic letters 18 (2016) 3090–3093; doi:10.1021/acs.orglett.6b01217

data_1543780
_publ_section_title
;
 Accessing Benzimidazoles via a Ring Distortion Strategy: An Oxone
 Mediated Tandem Reaction of 2-Aminobenzylamines.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3090
_journal_page_last               3093
_journal_paper_doi               10.1021/acs.orglett.6b01217
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C16 H16 N2 O, 0.5(H2 O)'
_chemical_formula_sum            'C16 H17 N2 O1.5'
_chemical_formula_weight         261.31
_chemical_name_systematic
'2-(4-methoxy-2,3-dimethylphenyl)-1H-benzo[d]imidazole, Water'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 93.756(9)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.441(4)
_cell_length_b                   8.216(2)
_cell_length_c                   26.040(7)
_cell_measurement_reflns_used    3342
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.58
_cell_measurement_theta_min      2.97
_cell_volume                     2656.0(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker PHOTON100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1140
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            23791
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.694
_diffrn_reflns_theta_min         2.973
_diffrn_source                   X-ray
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.917
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.488
_exptl_crystal_size_mid          0.244
_exptl_crystal_size_min          0.011
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0029(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2520
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0576
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0512P)^2^+2.3208P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1357
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1610
_reflns_number_total             2520
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01217_si_002.cif
_cod_data_source_block           IN_29
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-Scan' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/current/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 4268 2015-11-12 08:31:59Z antanas 

2017-03-19
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C16 H16 N2 O), H2 O'
_cod_original_formula_sum        'C32 H34 N4 O3'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     522.63
_cod_database_code               1543780
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.957
_shelx_estimated_absorpt_t_max   0.999
_shelx_res_checksum              31007
_shelx_hkl_checksum              61886