On the mechanism of benzimidazole synthesis via copper-catalysed intramolecular N-arylation
Jin, Xiaodong; Lin, Yongjie; Davies, Robert P.; Catalysis Science & Technology 13 (2023) 7181–7189; doi:10.1039/D3CY00767G

data_1570378
_publ_section_title
;
 On the mechanism of benzimidazole synthesis via copper-catalysed
 intramolecular N-arylation
;
_journal_issue                   24
_journal_name_full               'Catalysis Science &amp; Technology'
_journal_page_first              7181
_journal_page_last               7189
_journal_paper_doi               10.1039/D3CY00767G
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C36 H40 Cu4 I4 N8'
_chemical_formula_sum            'C36 H40 Cu4 I4 N8'
_chemical_formula_weight         1346.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-05-16 deposited with the CCDC.	2023-11-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.612(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.52910(20)
_cell_length_b                   22.9164(5)
_cell_length_c                   9.8700(2)
_cell_measurement_reflns_used    3840
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      73.7100
_cell_measurement_theta_min      3.8410
_cell_volume                     2103.33(8)
_computing_cell_refinement       CrysAlisPro,
_computing_data_collection       CrysAlisPro,
_computing_data_reduction        CrysAlisPro,
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10.4115
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device_type  'Agilent Xcalibur PX Ultra A'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6992
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.685
_diffrn_reflns_theta_min         3.858
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    25.609
_exptl_absorpt_correction_T_max  0.342
_exptl_absorpt_correction_T_min  0.046
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) 
(compiled Aug  2 2013,16:46:58) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    2.126
_exptl_crystal_description       plates
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.692
_refine_diff_density_min         -1.102
_refine_diff_density_rms         0.142
_refine_ls_extinction_coef       0.00033(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4018
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0320
_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^)+(0.0429P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0765
_refine_ls_wR_factor_ref         0.0791
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3686
_reflns_number_total             4018
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cy00767g2.cif
_cod_data_source_block           1a
_cod_depositor_comments
'Adding full bibliography for 1570378--1570383.cif.'
_cod_original_cell_volume        2103.34(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1570378
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              26877
_shelx_hkl_checksum              32274