Synthesis of 2-bromoimidazoles from alkynes, N-sulfonylazides, and bromocyanides.
Lee, Eunsook; Ryu, Taekyu; Shin, Eunji; Son, Jeong-Yu; Choi, Wonseok; Lee, Phil Ho; Organic letters 17 (2015) 2470–2473; doi:10.1021/acs.orglett.5b00977

data_1529350
_publ_section_title
;
 Synthesis of 2-bromoimidazoles from alkynes, N-sulfonylazides, and
 bromocyanides.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2470
_journal_page_last               2473
_journal_paper_doi               10.1021/acs.orglett.5b00977
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C16 H10 Br F3 N2 O2 S'
_chemical_formula_weight         431.23
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 101.3010(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.4371(3)
_cell_length_b                   13.3473(3)
_cell_length_c                   22.4306(7)
_cell_measurement_reflns_used    9897
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.8516
_cell_measurement_theta_min      2.3719
_cell_volume                     3357.74(16)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_laue_measured_fraction_full 1.000
_diffrn_reflns_laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            48741
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.379
_diffrn_reflns_theta_min         1.785
_exptl_absorpt_coefficient_mu    2.616
_exptl_absorpt_correction_T_max  0.68
_exptl_absorpt_correction_T_min  0.61
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_description       block
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_refine_diff_density_max         1.293
_refine_diff_density_min         -1.026
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         4190
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0665
_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^)+(0.0803P)^2^+20.9101P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1674
_refine_ls_wR_factor_ref         0.1872
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3095
_reflns_number_total             4190
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b00977_si_002.cif
_cod_data_source_block           CCDC1054120
_cod_database_code               1529350
_shelxl_version_number           2013-4
_shelx_res_checksum              15854
_shelx_hkl_checksum              54313