Synthesis of fused benzimidazoles via successive nucleophilic additions of benzimidazole derivatives to arynes under transition metal-free conditions
Li, Bingnan; Mai, Shaoyu; Song, Qiuling; Organic Chemistry Frontiers 5 (2018) 1639–; doi:10.1039/C8QO00251G

data_1554292
_publ_section_title
;
 Synthesis of fused benzimidazoles via successive nucleophilic additions
 of benzimidazole derivatives to arynes under transition metal-free
 conditions
;
_journal_issue                   10
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1639
_journal_paper_doi               10.1039/C8QO00251G
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C21 H16 N2 O, C4 H4 O2'
_chemical_formula_sum            'C25 H20 N2 O3'
_chemical_formula_weight         396.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-03-07
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-03-08 deposited with the CCDC.
2018-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                94.495(10)
_cell_angle_beta                 95.250(10)
_cell_angle_gamma                98.331(7)
_cell_formula_units_Z            2
_cell_length_a                   9.0455(8)
_cell_length_b                   9.9480(9)
_cell_length_c                   11.7172(17)
_cell_measurement_reflns_used    1828
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.0150
_cell_measurement_theta_min      3.3230
_cell_volume                     1034.4(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     -1.00  76.00   1.00    7.50    --   16.81  57.00 -30.00   77
  2  \w     52.00  88.00   1.00    7.50    --   16.81 178.00 120.00   36
  3  \w    -21.00  83.00   1.00    7.50    --   16.81  19.00 -90.00  104
  4  \w    -23.00  23.00   1.00    7.50    --  -17.43 -99.00-180.00   46
  5  \w    -24.00   3.00   1.00    7.50    --  -17.43 -99.00  60.00   27
  6  \w    -49.00  37.00   1.00    7.50    --   16.81 -77.00 120.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0164965000
_diffrn_orient_matrix_UB_12      -0.0721833000
_diffrn_orient_matrix_UB_13      -0.0030879000
_diffrn_orient_matrix_UB_21      0.0137256000
_diffrn_orient_matrix_UB_22      -0.0041187000
_diffrn_orient_matrix_UB_23      -0.0587159000
_diffrn_orient_matrix_UB_31      0.0767410000
_diffrn_orient_matrix_UB_32      -0.0032689000
_diffrn_orient_matrix_UB_33      0.0164482000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_unetI/netI     0.0778
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7650
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.85
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4214
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.1661
_refine_ls_R_factor_gt           0.1274
_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^)+(0.1320P)^2^+3.4700P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3304
_refine_ls_wR_factor_ref         0.3582
_reflns_number_gt                2657
_reflns_number_total             4214
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8qo00251g2.cif
_cod_data_source_block           exp_3993
_cod_database_code               1554292
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C5(H5), C3(H3), C4(H4), C6(H6), C10(H10), C9(H9), C11(H11),
 C20(H20), C16(H16), C17(H17), C18(H18), C24(H24)
2.b Idealised Me refined as rotating group:
 C21(H21a,H21b,H21c), C22(H22a,H22b,H22c)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.372
_oxdiff_exptl_absorpt_empirical_full_min 0.574