Base-Mediated Regioselective [3+2] Annulation of Ketenimines and Isocyanides: Efficient Synthesis of 1,4,5-Trisubstituted lmidazoles
Cai, Jinxiong; Bai, Haijie; Wang, Yuan; Xu, Xianxiu; Xie, Haiming; Liu, Jun; Chemical Communications  (2019) –; doi:10.1039/C9CC01257E

data_7123120
_publ_section_title
;
 Base-Mediated Regioselective [3+2] Annulation of Ketenimines and
 Isocyanides: Efficient Synthesis of 1,4,5-Trisubstituted lmidazoles
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC01257E
_journal_year                    2019
_chemical_formula_sum            'C29 H23 I N2 O2 S'
_chemical_formula_weight         590.45
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2019-02-11 deposited with the CCDC.    2019-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 107.411(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.861(7)
_cell_length_b                   15.356(9)
_cell_length_c                   13.575(7)
_cell_measurement_reflns_used    164
_cell_measurement_temperature    283(2)
_cell_measurement_theta_max      23.55
_cell_measurement_theta_min      2.83
_cell_volume                     2558(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      283(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CMOS area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            35806
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.09
_diffrn_reflns_theta_min         2.65
_exptl_absorpt_coefficient_mu    1.362
_exptl_absorpt_correction_T_max  0.8115
_exptl_absorpt_correction_T_min  0.7629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.160
_refine_diff_density_min         -1.295
_refine_diff_density_rms         0.339
_refine_ls_extinction_coef       0.0263(18)
_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   1.111
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         5046
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0652
_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^)+(0.1085P)^2^+3.0901P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1640
_refine_ls_wR_factor_ref         0.2022
_reflns_number_gt                3454
_reflns_number_total             5046
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9cc01257e2.cif
_cod_data_source_block           liujun181221_1_0m_a
_cod_original_sg_symbol_H-M      p2(1)/c
_cod_database_code               7123120