(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_4036227
_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         'C31 H19 Br N5 O2'
_chemical_formula_sum            'C31 H19 Br N5 O2'
_chemical_formula_weight         573.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-04-28
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.4220(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8254(3)
_cell_length_b                   12.7608(3)
_cell_length_c                   18.3146(5)
_cell_measurement_reflns_used    9881
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.20
_cell_measurement_theta_min      2.70
_cell_volume                     2927.24(13)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.06
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            59680
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.350
_diffrn_reflns_theta_min         1.773
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.439
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1401 before and 0.0599 after correction.
The Ratio of minimum to maximum transmission is 0.7423.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       plate
_exptl_crystal_F_000             1164
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.641
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         7293
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0395
_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^)+(0.0521P)^2^+0.5176P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1095
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5328
_reflns_number_total             7293
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b00955_si_002.cif
_cod_data_source_block           18e
_cod_database_code               4036227
_shelx_estimated_absorpt_t_max   0.869
_shelx_estimated_absorpt_t_min   0.672
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N5(H5), C12(H12), C8(H8), C13(H13), C31(H31), C25(H25), C19(H19), C21(H21),
 C22(H22), C6(H6), C2(H2), C20(H20), C4(H4), C14(H14), C15(H15), C30(H30),
 C29(H29), C28(H28), C3(H3)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'