Rational synthesis of benzimidazole[3]arenes by Cu<sup>II</sup>-catalyzed post-macrocyclization transformation.
Tashiro, Shohei; Umeki, Tsutomu; Kubota, Ryou; Shionoya, Mitsuhiko; Chemical science 9 (2018) 7614–7619; doi:10.1039/c8sc03086c

data_1549878
_publ_section_title
;
 Rational synthesis of benzimidazole[3]arenes by Cu<sup>II</sup>-catalyzed
 post-macrocyclization transformation.
;
_journal_issue                   39
_journal_name_full               'Chemical science'
_journal_page_first              7614
_journal_page_last               7619
_journal_paper_doi               10.1039/c8sc03086c
_journal_volume                  9
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         '(C42 H30 N6), 2(C H Cl3)'
_chemical_formula_sum            'C44 H32 Cl6 N6'
_chemical_formula_weight         857.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2017-11-15 deposited with the CCDC.
2018-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.020(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7565(5)
_cell_length_b                   25.735(2)
_cell_length_c                   26.340(2)
_cell_measurement_reflns_used    10242
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.10
_cell_volume                     3901.5(5)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_publication_material  'CrystalStructure 4.1'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            15995
_diffrn_reflns_point_group_measured_fraction_full 0.884
_diffrn_reflns_point_group_measured_fraction_max 0.883
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         3.094
_exptl_absorpt_coefficient_mu    0.483
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_correction_T_min  0.745
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1760
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform-acetone'
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.796
_refine_diff_density_min         -0.686
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details
;
 Flack x determined using 1440 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         6373
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.1361
_refine_ls_R_factor_gt           0.0911
_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^)+(0.1806P)^2^+4.4625P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2388
_refine_ls_wR_factor_ref         0.2893
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    0.770
_reflns_Friedel_fraction_max     0.766
_reflns_number_gt                4159
_reflns_number_total             6373
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc03086c2.cif
_cod_data_source_block           anti-benzimidazole[3]arene
_cod_depositor_comments
'Adding full bibliography for 1549877--1549879.cif.'
_cod_original_cell_volume        3901.4(6)
_cod_database_code               1549878
_shelx_estimated_absorpt_t_min   0.889
_shelx_estimated_absorpt_t_max   0.953
_shelxl_version_number           2013-4
_shelx_res_checksum              95566