(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_4036225
_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 H18 N4 O4 S'
_chemical_formula_sum            'C28 H18 N4 O4 S'
_chemical_formula_weight         506.52
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-04-27
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                70.052(2)
_cell_angle_beta                 80.005(2)
_cell_angle_gamma                72.616(2)
_cell_formula_units_Z            4
_cell_length_a                   13.0814(4)
_cell_length_b                   14.4208(5)
_cell_length_c                   14.7793(5)
_cell_measurement_reflns_used    9878
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.25
_cell_measurement_theta_min      2.45
_cell_volume                     2493.06(15)
_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      99.99
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_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  0.0338
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            49498
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.349
_diffrn_reflns_theta_min         1.470
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0543 before and 0.0440 after correction.
The Ratio of minimum to maximum transmission is 0.9060.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       plate
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.659
_refine_diff_density_min         -0.731
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     695
_refine_ls_number_reflns         10133
_refine_ls_number_restraints     34
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0443
_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^)+(0.0586P)^2^+1.0137P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1197
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8078
_reflns_number_total             10133
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b00955_si_002.cif
_cod_data_source_block           16i
_cod_database_code               4036225
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.966
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 C12-C11
 1.38 with sigma of 0.02
 C11-C12A
 1.38 with sigma of 0.02
 C44-C45
 1.38 with sigma of 0.02
 C45A-C46A
 1.38 with sigma of 0.02
 C44-C45A
 1.38 with sigma of 0.02
 C12-C13
 1.38 with sigma of 0.02
 C44-S2A
 1.71 with sigma of 0.02
 S2A-C47A
 1.71 with sigma of 0.02
 C12A-C14
 1.38 with sigma of 0.02
 C46A-C47A
 1.41 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C46) \\sim Ueq, Uanis(C47A) \\sim Ueq, Uanis(C46A) \\sim Ueq, Uanis(C47)
\\sim Ueq: with sigma of 0.03 and sigma for terminal atoms of 0.03
Uanis(C47) = Uanis(C47A) = Uanis(C46) = Uanis(C46A)
Uanis(S2) = Uanis(S2A)
Uanis(C45) = Uanis(C45A)
Uanis(C12) = Uanis(C12A)
4. Others
 Sof(S2)=Sof(C45)=Sof(H45)=Sof(C46)=Sof(H46)=Sof(C47)=Sof(H47)=1-FVAR(1)
 Sof(C45A)=Sof(H45A)=Sof(S2A)=Sof(C47A)=Sof(H47A)=Sof(C46A)=Sof(H46A)=FVAR(1)
 Sof(S1B)=Sof(H14A)=Sof(H13B)=Sof(C12A)=Sof(H12B)=1-FVAR(2)
 Sof(S1A)=Sof(H14)=Sof(H13A)=Sof(C12)=Sof(H12A)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C65(H65A,H65B)
5.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C7(H7), C5(H5), C6(H6), C14(H14), C14(H14A), C13(H13B), C13(H13A),
 C16(H16), C22(H22), C15(H15), N15(H15A), C30(H30), C33(H33), C31(H31),
 C32(H32), C63(H63), C60(H60), C64(H64), C40(H40), C37(H37), C39(H39), C38(H38),
  C45A(H45A), C47A(H47A), C46A(H46A), N13(H13), C57(H57), C55(H55), C56(H56),
 C54(H54), C12(H12A), C45(H45), C46(H46), C47(H47), C12A(H12B)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'