Ag-Catalyzed Tandem Three-Component Reaction toward the Synthesis of Multisubstituted Imidazoles.
Wang, Changcheng; Lai, Jialin; Chen, Cantao; Li, Xuechen; Cao, Hua; The Journal of organic chemistry 82 (2017) 13740–13745; doi:10.1021/acs.joc.7b02612

data_4033241
_publ_section_title
;
 Ag-Catalyzed Tandem Three-Component Reaction toward the Synthesis of
 Multisubstituted Imidazoles.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13740
_journal_page_last               13745
_journal_paper_doi               10.1021/acs.joc.7b02612
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C24 H20 N2 O2'
_chemical_formula_sum            'C24 H20 N2 O2'
_chemical_formula_weight         368.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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     dual
_audit_creation_date             2017-09-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.622(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.9318(7)
_cell_length_b                   9.1249(3)
_cell_length_c                   11.0844(4)
_cell_measurement_reflns_used    6536
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.6780
_cell_measurement_theta_min      5.3710
_cell_volume                     1911.01(12)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -42.00  -4.00   0.50    0.50    --    0.00 -19.00  90.00   76
  2  \w    -70.00  -9.00   0.50    0.50    --    0.00 -38.00 -90.00  122
  3  \w    -14.00  88.00   0.50    0.50    --    0.00  38.00  60.00  204
  4  \w     80.00 177.00   0.50    0.50    --   95.20  30.00  90.00  194
  5  \w     64.00 164.00   0.50    0.50    --   95.20  82.00 -60.00  200
  6  \w     22.00 118.00   0.50    0.50    --   95.20 -61.00-180.00  192
  7  \w    151.00 177.00   0.50    0.50    --   95.20  30.00 -90.00   52
  8  \w     85.00 184.00   0.50    0.50    --   95.20  30.00  60.00  198
  9  \w     42.00  84.00   0.50    0.50    --   95.20 -45.00-180.00   84
 10  \w     86.00 170.00   0.50    0.50    --   95.20  15.00  30.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0662046000
_diffrn_orient_matrix_UB_12      -0.0447741000
_diffrn_orient_matrix_UB_13      -0.0792807000
_diffrn_orient_matrix_UB_21      0.0392697000
_diffrn_orient_matrix_UB_22      -0.1366261000
_diffrn_orient_matrix_UB_23      -0.0428214000
_diffrn_orient_matrix_UB_31      -0.0267683000
_diffrn_orient_matrix_UB_32      -0.0886188000
_diffrn_orient_matrix_UB_33      0.1062438000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10178
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.139
_diffrn_reflns_theta_min         2.338
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.654
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.752
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       0.0012(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3771
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.1225
_refine_ls_R_factor_gt           0.1189
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0943P)^2^+19.2905P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3425
_refine_ls_wR_factor_ref         0.3437
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3455
_reflns_number_total             3771
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02612_si_002.cif
_cod_data_source_block           d4
_cod_depositor_comments          'Adding full bibliography for 4033241.cif.'
_cod_database_code               4033241
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.932
_shelx_estimated_absorpt_t_min   0.897
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C9(H9), C15(H15), C20(H20), C5(H5), C7(H7), C8(H8), C11(H11),
 C18(H18), C19(H19), C14(H14), C22(H22), C13(H13), C12(H12), C21(H21)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.665
_oxdiff_exptl_absorpt_empirical_full_min 0.655