Cascade Synthesis of Benzimidazole-Linked Pyrroles via Copper Catalyzed Oxidative Cyclization and Ketonization.
Ye, Tzuen-Yang; Selvaraju, Manikandan; Sun, Chung-Ming; Organic letters 19 (2017) 3103–3106; doi:10.1021/acs.orglett.7b01224

data_1546241
_publ_section_title
;
 Cascade Synthesis of Benzimidazole-Linked Pyrroles via Copper Catalyzed
 Oxidative Cyclization and Ketonization.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3103
_journal_page_last               3106
_journal_paper_doi               10.1021/acs.orglett.7b01224
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C41 H34 F3 N3 O2'
_chemical_formula_weight         657.71
_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   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                105.485(7)
_cell_angle_beta                 106.870(7)
_cell_angle_gamma                99.403(8)
_cell_formula_units_Z            2
_cell_length_a                   9.5081(13)
_cell_length_b                   13.6271(19)
_cell_length_c                   14.3689(19)
_cell_measurement_reflns_used    7005
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.1810
_cell_measurement_theta_min      2.2992
_cell_volume                     1657.4(4)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            24895
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.913
_diffrn_reflns_theta_min         1.571
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9484
_exptl_absorpt_correction_T_min  0.8600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Tabullar
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.667
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     480
_refine_ls_number_reflns         6763
_refine_ls_number_restraints     132
_refine_ls_restrained_S_all      1.174
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0483
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0701P)^2^+0.1239P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1265
_refine_ls_wR_factor_ref         0.1394
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5072
_reflns_number_total             6763
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01224_si_003.cif
_cod_data_source_block           160413lt_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 1546241--1546242.cif.
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_cod_database_code               1546241
_shelxl_version_number           2014/6
_shelx_res_checksum              91703
_shelx_hkl_checksum              41963