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_1549877
_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_formula_moiety         '(C42 H30 N6), 2(C H2 Cl2), 1.5(H2 O)'
_chemical_formula_sum            'C44 H37 Cl4 N6 O1.5'
_chemical_formula_weight         815.59
_space_group_crystal_system      trigonal
_space_group_IT_number           167
_space_group_name_Hall           '-R 3 2"c'
_space_group_name_H-M_alt        'R -3 c :H'
_symmetry_space_group_name_Hall  '-R 3 2"c'
_symmetry_space_group_name_H-M   'R -3 c :H'
_atom_sites_solution_hydrogens   mixed
_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                 90
_cell_angle_gamma                120
_cell_formula_units_Z            12
_cell_length_a                   16.5210(5)
_cell_length_b                   16.5210(5)
_cell_length_c                   49.1998(17)
_cell_measurement_reflns_used    30483
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.23
_cell_volume                     11629.6(6)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0311
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       63
_diffrn_reflns_limit_l_min       -63
_diffrn_reflns_number            34693
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_min         3.294
_exptl_absorpt_coefficient_mu    0.352
_exptl_absorpt_correction_T_max  0.916
_exptl_absorpt_correction_T_min  0.723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             5076
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile-dichloromethane'
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.554
_refine_diff_density_min         -1.304
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2970
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0486
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0682P)^2^+46.3930P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1341
_refine_ls_wR_factor_ref         0.1371
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2575
_reflns_number_total             2970
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc03086c2.cif
_cod_data_source_block           syn-benzimidazole[3]arene
_cod_depositor_comments
'Adding full bibliography for 1549877--1549879.cif.'
_cod_original_cell_volume        11629.6(8)
_cod_original_formula_sum        'C44 H37 Cl4 N6 O1.50'
_cod_database_code               1549877
_shelx_estimated_absorpt_t_min   0.844
_shelx_estimated_absorpt_t_max   0.917
_shelxl_version_number           2013-4
_shelx_res_checksum              31089