Three-component reaction of propargyl amines, sulfonyl azides, and alkynes: one-pot synthesis of tetrasubstituted imidazoles.
Jiang, Zheng; Lu, Ping; Wang, Yanguang; Organic letters 14 (2012) 6266–6269; doi:10.1021/ol303023y

data_1508799
_publ_section_title
;
 Three-component reaction of propargyl amines, sulfonyl azides, and
 alkynes: one-pot synthesis of tetrasubstituted imidazoles.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6266
_journal_page_last               6269
_journal_paper_doi               10.1021/ol303023y
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C37 H32 N2 O2 S'
_chemical_formula_sum            'C37 H32 N2 O2 S'
_chemical_formula_weight         568.71
_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                 113.887(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.1421(18)
_cell_length_b                   10.9109(7)
_cell_length_c                   18.5908(16)
_cell_measurement_reflns_used    2579
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5097
_cell_measurement_theta_min      3.2075
_cell_volume                     2993.8(5)
_computing_cell_refinement       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\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  0.0577
_diffrn_reflns_av_sigmaI/netI    0.0766
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12502
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.29
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_T_max  0.9786
_exptl_absorpt_correction_T_min  0.9675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis PRO (Agilent Technologies, 2011) 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.705
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         5473
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.1472
_refine_ls_R_factor_gt           0.0894
_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^)+(0.0853P)^2^+4.5523P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2242
_refine_ls_wR_factor_ref         0.2567
_reflns_number_gt                3177
_reflns_number_total             5473
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol303023y_si_002.cif
_cod_data_source_block           111124_jz_6
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1508799