A Facile FeCl3/I2-Catalyzed Aerobic Oxidative Coupling Reaction: Synthesis of Tetrasubstituted Imidazoles from Amidines and Chalcones.
Zhu, Yuelu; Li, Cheng; Zhang, Jidong; She, Mengyao; Sun, Wei; Wan, Kerou; Wang, Yaqi; Yin, Bin; Liu, Ping; Li, Jianli; Organic letters 17 (2015) 3872–3875; doi:10.1021/acs.orglett.5b01854

data_1529855
_publ_section_title
;
 A Facile FeCl3/I2-Catalyzed Aerobic Oxidative Coupling Reaction:
 Synthesis of Tetrasubstituted Imidazoles from Amidines and Chalcones.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3872
_journal_page_last               3875
_journal_paper_doi               10.1021/acs.orglett.5b01854
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C26 H18 N2 O S'
_chemical_formula_weight         406.48
_space_group_IT_number           14
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.942(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.919(2)
_cell_length_b                   19.032(4)
_cell_length_c                   11.221(2)
_cell_measurement_reflns_used    1007
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.18
_cell_measurement_theta_min      2.36
_cell_volume                     2064.5(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART APEX II'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_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_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_sigmaI/netI    0.0666
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10469
_diffrn_reflns_theta_full        25.36
_diffrn_reflns_theta_max         25.36
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0029(6)
_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   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         3762
_refine_ls_number_restraints     189
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0510
_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^)+(0.0320P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.1055
_reflns_number_gt                2202
_reflns_number_total             3762
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b01854_si_003.cif
_cod_data_source_block           x
_cod_original_cell_volume        2064.4(8)
_cod_database_code               1529855