(Z)-Stereoselective Synthesis of Mono- and Bis-heterocyclic Benzimidazol-2-ones via Cascade Processes Coupled with the Ugi Multicomponent Reaction.
Xu, Zhigang; Martinez-Ariza, Guillermo; Cappelli, Alexandra P.; Roberts, Sue A.; Hulme, Christopher; The Journal of organic chemistry 80 (2015) 9007–9015; doi:10.1021/acs.joc.5b00955

data_4036223
_publ_section_title
;
 (Z)-Stereoselective Synthesis of Mono- and Bis-heterocyclic
 Benzimidazol-2-ones via Cascade Processes Coupled with the Ugi
 Multicomponent Reaction.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9007
_journal_page_last               9015
_journal_paper_doi               10.1021/acs.joc.5b00955
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C28 H19 F N3 O5, C H2 Cl2'
_chemical_formula_sum            'C29 H21 Cl2 F N3 O5'
_chemical_formula_weight         581.39
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.6808(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.3709(3)
_cell_length_b                   13.2507(3)
_cell_length_c                   17.9850(4)
_cell_measurement_reflns_used    4303
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.18
_cell_measurement_theta_min      2.27
_cell_volume                     2700.80(11)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXTL and local programs'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa APEXII DUO CCD diffractometer'
_diffrn_measurement_method       'thin-slice \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube with Miracol optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            77173
_diffrn_reflns_theta_full        25.71
_diffrn_reflns_theta_max         25.078
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.293
_exptl_absorpt_correction_T_max  0.9736
_exptl_absorpt_correction_T_min  0.9352
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'TWINABS; Sheldrick, 1996'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1196
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.798
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0044(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     443
_refine_ls_number_reflns         5143
_refine_ls_number_restraints     51
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0465
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0584P)^2^+2.8161P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1253
_reflns_number_gt                3977
_reflns_number_total             4798
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo5b00955_si_002.cif
_cod_data_source_block           7a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4036223