Aryl Azides as Forgotten Electrophiles in the Van Leusen Reaction: A Multicomponent Transformation Affording 4-Tosyl-1-arylimidazoles.
Necardo, Cristiana; Alfano, Antonella Ilenia; Del Grosso, Erika; Pelliccia, Sveva; Galli, Ubaldina; Novellino, Ettore; Meneghetti, Fiorella; Giustiniano, Mariateresa; Tron, Gian Cesare; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02546

data_4037643
_publ_section_title
;
 Aryl Azides as Forgotten Electrophiles in the Van Leusen Reaction: A
 Multicomponent Transformation Affording 4-Tosyl-1-arylimidazoles.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02546
_journal_year                    2019
_chemical_formula_sum            'C16 H14 N2 O2 S'
_chemical_formula_weight         298.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7417(9)
_cell_length_b                   9.3943(15)
_cell_length_c                   27.095(4)
_cell_measurement_reflns_used    3143
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23
_cell_measurement_theta_min      2
_cell_volume                     1461.5(4)
_computing_cell_refinement       'SAINT (Bruker-Axs Inc)'
_computing_data_collection       'SMART (Bruker-Axs Inc)'
_computing_data_reduction        'SAINT (Bruker-Axs Inc)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SIR-97 for Windows (Altomare, 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker-Axs Smart-Apex CCD'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            11244
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.063
_diffrn_reflns_theta_max         25.063
_diffrn_reflns_theta_min         1.503
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tabular
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.116
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 833 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2585
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0348
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0483P)^2^+0.1751P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.0929
_reflns_Friedel_coverage         0.679
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2290
_reflns_number_total             2585
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02546_si_002.cif
_cod_data_source_block           shelxl
_cod_database_code               4037643
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              37954
_shelx_hkl_checksum              20776