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_1570379
_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, C7 H8'
_chemical_formula_sum            'C43 H48 Cu4 I4 N8'
_chemical_formula_weight         1438.65
_space_group_crystal_system      orthorhombic
_space_group_IT_number           52
_space_group_name_Hall           '-P 2a 2bc'
_space_group_name_H-M_alt        'P n n a'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.0759(2)
_cell_length_b                   16.97565(17)
_cell_length_c                   14.15214(16)
_cell_measurement_reflns_used    5613
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      73.5700
_cell_measurement_theta_min      3.8050
_cell_volume                     4823.07(9)
_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 0.992
_diffrn_measured_fraction_theta_max 0.963
_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  0.0199
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9477
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.813
_diffrn_reflns_theta_min         3.821
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    22.389
_exptl_absorpt_correction_T_max  0.332
_exptl_absorpt_correction_T_min  0.131
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
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    1.981
_exptl_crystal_description       tablets
_exptl_crystal_F_000             2760
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.844
_refine_diff_density_min         -0.796
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       0.000180(10)
_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   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4704
_refine_ls_number_restraints     52
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0261
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0340P)^2^+2.5181P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0640
_refine_ls_wR_factor_ref         0.0662
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4248
_reflns_number_total             4704
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cy00767g2.cif
_cod_data_source_block           1a-tol
_cod_depositor_comments
'Adding full bibliography for 1570378--1570383.cif.'
_cod_original_cell_volume        4823.06(9)
_cod_database_code               1570379
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              30854
_shelx_hkl_checksum              25132