Synthesis of Benzimidazolones via One-Pot Reaction of Hydroxylamines, Aldehydes, and Trimethylsilyl Cyanide Promoted by Diacetoxyiodobenzene.
Zhang, Huaiyuan; Huang, Danfeng; Wang, Ke-Hu; Li, Jun; Su, Yingpeng; Hu, Yulai; The Journal of organic chemistry 82 (2017) 1600–1609; doi:10.1021/acs.joc.6b02781

data_4032333
_publ_section_title
;
 Synthesis of Benzimidazolones via One-Pot Reaction of Hydroxylamines,
 Aldehydes, and Trimethylsilyl Cyanide Promoted by Diacetoxyiodobenzene.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1600
_journal_page_last               1609
_journal_paper_doi               10.1021/acs.joc.6b02781
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C16 H14 N2 O3'
_chemical_formula_sum            'C16 H14 N2 O3'
_chemical_formula_weight         282.29
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-06-29
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_cell_angle_alpha                71.905(6)
_cell_angle_beta                 71.569(6)
_cell_angle_gamma                61.983(7)
_cell_formula_units_Z            2
_cell_length_a                   9.0314(6)
_cell_length_b                   9.1791(7)
_cell_length_c                   10.9270(6)
_cell_measurement_reflns_used    1561
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.2860
_cell_measurement_theta_min      3.9880
_cell_volume                     744.33(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega    1.00   66.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   57.0000    0.0000 65

  2 omega   -5.00   85.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   38.0000 -150.0000 90

  3 omega   -3.00   48.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -99.0000  -90.0000 51

  4 omega  -38.00  -11.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -57.0000    0.0000 27

  5 omega  -52.00   46.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -38.0000   30.0000 98

  6 omega  -15.00   19.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000  150.0000 34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0887256000
_diffrn_orient_matrix_UB_12      0.0467188000
_diffrn_orient_matrix_UB_13      0.0219653000
_diffrn_orient_matrix_UB_21      -0.0100707000
_diffrn_orient_matrix_UB_22      -0.0759688000
_diffrn_orient_matrix_UB_23      0.0312199000
_diffrn_orient_matrix_UB_31      0.0167505000
_diffrn_orient_matrix_UB_32      0.0024225000
_diffrn_orient_matrix_UB_33      0.0583663000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4759
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         3.60
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2818
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0562
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0473P)^2^+0.2179P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1546
_reflns_number_gt                1857
_reflns_number_total             2818
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02781_si_002.cif
_cod_data_source_block           zhanghy0623
_cod_original_cell_volume        744.33(9)
_cod_database_code               4032333
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_olex2_date_sample_data_collection 2015-06-23
_olex2_submission_special_instructions 'No special instructions were received'