Selective C(sp(2))-H Halogenation of "Click" 4-Aryl-1,2,3-triazoles.
Goitia, Asier; Gómez-Bengoa, Enrique; Correa, Arkaitz; Organic letters 19 (2017) 962–965; doi:10.1021/acs.orglett.7b00275

data_1545450
_publ_section_title
;
 Selective C(sp(2))-H Halogenation of &quot;Click&quot;
 4-Aryl-1,2,3-triazoles.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              962
_journal_page_last               965
_journal_paper_doi               10.1021/acs.orglett.7b00275
_journal_volume                  19
_journal_year                    2017
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C16 H13 Br F N3'
_chemical_formula_sum            'C16 H13 Br F N3'
_chemical_formula_weight         346.2
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-12-05T14:30:55-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                78.631(5)
_cell_angle_beta                 74.036(5)
_cell_angle_gamma                64.658(6)
_cell_formula_units_Z            4
_cell_length_a                   9.9538(6)
_cell_length_b                   11.0301(8)
_cell_length_c                   15.5083(9)
_cell_measurement_reflns_used    2982
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      74.582
_cell_measurement_theta_min      5.037
_cell_measurement_wavelength     1.54184
_cell_volume                     1473.29(18)
_computing_cell_refinement       'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_data_collection       'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_data_reduction        'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_molecular_graphics    'Diamond v.3.2f (Crystal Impact GbR, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'OLEX2 (Dolomanov et al, 2009)'
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9863
_diffrn_measured_fraction_theta_max 0.9458
_diffrn_measurement_details
;
  1 omega   17.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6321   38.0000 -120.0000 65

  2 omega   83.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6321   38.0000 -120.0000 27

  3 omega   37.00   68.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1793  -30.0000  -30.0000 31

  4 omega   43.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1793  -30.0000  -60.0000 26

  5 omega   43.00   74.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1793  -45.0000    0.0000 31

  6 omega   33.00   67.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1793  -30.0000   30.0000 34

  7 omega   33.00   63.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1793  -30.0000   90.0000 30

  8 omega   45.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1793  -45.0000  120.0000 32

  9 omega   46.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1793  -94.0000  150.0000 58

 10 omega   57.00  121.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1793 -125.0000   60.0000 64

 11 omega   49.00   87.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1793  -94.0000   90.0000 38

 12 omega   34.00   68.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1793  -30.0000  150.0000 34

 13 omega  109.00  137.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1793   30.0000   90.0000 28

 14 omega   77.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1793   77.0000  -30.0000 27

 15 omega  121.00  148.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1793   77.0000  -30.0000 27

 16 omega  124.00  152.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1793   61.0000 -150.0000 28

 17 omega   85.00  154.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1793   30.0000  -30.0000 69

 18 omega   45.00  131.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1793  -77.0000 -150.0000 86

 19 omega   34.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1793  -30.0000 -150.0000 35

 20 omega   34.00   63.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1793  -30.0000 -180.0000 29

 21 omega   11.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6321 -130.0000  -16.0000 78

 22 omega   33.00   63.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1793  -30.0000   60.0000 30

 23 omega    3.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6321 -125.0000   60.0000 95

 24 omega   17.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6321   38.0000  150.0000 85
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0443059
_diffrn_orient_matrix_UB_12      -0.0376623
_diffrn_orient_matrix_UB_13      -0.0974114
_diffrn_orient_matrix_UB_21      0.0031987
_diffrn_orient_matrix_UB_22      0.1395802
_diffrn_orient_matrix_UB_23      -0.0355996
_diffrn_orient_matrix_UB_31      0.1696392
_diffrn_orient_matrix_UB_32      -0.056416
_diffrn_orient_matrix_UB_33      0.0030329
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Nova (Cu) X-ray micro-source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0695
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5602
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.994
_diffrn_reflns_theta_min         4.454
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    3.873
_exptl_absorpt_correction_T_max  0.874
_exptl_absorpt_correction_T_min  0.233
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_size_max          1.0726
_exptl_crystal_size_mid          0.0658
_exptl_crystal_size_min          0.0411
_refine_diff_density_max         1.095
_refine_diff_density_min         -0.821
_refine_diff_density_rms         0.131
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         5602
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.976
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0577
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1263P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1587
_refine_ls_wR_factor_ref         0.1778
_reflns_number_gt                3946
_reflns_number_total             5602
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00275_si_003.cif
_cod_data_source_block           a20160316_ag90b
_cod_database_code               1545450