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_1549879
_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), 3(C7 H8 S O3), 3(O H2)'
_chemical_formula_sum            'C63 H60 N6 O12 S3'
_chemical_formula_weight         1189.35
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_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                98.632(2)
_cell_angle_beta                 94.107(2)
_cell_angle_gamma                107.170(2)
_cell_formula_units_Z            2
_cell_length_a                   9.9758(3)
_cell_length_b                   14.1235(3)
_cell_length_c                   21.6617(4)
_cell_measurement_reflns_used    10031
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      73.87
_cell_measurement_theta_min      3.32
_cell_volume                     2861.15(12)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_publication_material  'CrystalStructure 4.2.4'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 5.811
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            32111
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.436
_diffrn_reflns_theta_min         3.329
_exptl_absorpt_coefficient_mu    1.768
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       plate
_exptl_crystal_F_000             1248
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane'
_exptl_crystal_size_max          0.079
_exptl_crystal_size_mid          0.043
_exptl_crystal_size_min          0.028
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     800
_refine_ls_number_reflns         11270
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0488
_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^)+(0.0641P)^2^+1.3566P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1241
_refine_ls_wR_factor_ref         0.1332
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8644
_reflns_number_total             11270
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc03086c2.cif
_cod_data_source_block           protonated_anti-benzimidazole[3]arene
_cod_depositor_comments
'Adding full bibliography for 1549877--1549879.cif.'
_cod_original_cell_volume        2861.14(12)
_cod_database_code               1549879
_shelx_estimated_absorpt_t_min   0.873
_shelx_estimated_absorpt_t_max   0.952
_shelxl_version_number           2013-4
_shelx_res_checksum              13117