I2/TBPB Mediated Oxidative Reaction of N-Tosylhydrazones with Anilines: Practical Construction of 1,4-Disubstituted 1,2,3-Triazoles under Metal-Free and Azide-Free Conditions.
Cai, Zhong-Jian; Lu, Xin-Mou; Zi, You; Yang, Chao; Shen, Ling-Jie; Li, Jian; Wang, Shun-Yi; Ji, Shun-Jun; Organic letters 16 (2014) 5108–5111; doi:10.1021/ol502431b

data_1517830
_publ_section_title
;
 I2/TBPB Mediated Oxidative Reaction of N-Tosylhydrazones with Anilines:
 Practical Construction of 1,4-Disubstituted 1,2,3-Triazoles under
 Metal-Free and Azide-Free Conditions.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5108
_journal_page_last               5111
_journal_paper_doi               10.1021/ol502431b
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C15 H11 Br N3'
_chemical_formula_sum            'C15 H12 Br N3'
_chemical_formula_weight         314.19
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2yc'
_space_group_name_H-M_alt        'I 1 2/c 1'
_symmetry_space_group_name_Hall  '-I 2yc'
_symmetry_space_group_name_H-M   'I 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-04-23
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.358(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3641(5)
_cell_length_b                   5.6583(4)
_cell_length_c                   31.688(2)
_cell_measurement_reflns_used    1131
_cell_measurement_temperature    291.47(10)
_cell_measurement_theta_max      29.6260
_cell_measurement_theta_min      3.8580
_cell_volume                     1318.12(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS-1997 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291.47(10)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0568224000
_diffrn_orient_matrix_UB_12      0.0915773000
_diffrn_orient_matrix_UB_13      0.0069502000
_diffrn_orient_matrix_UB_21      0.0777950000
_diffrn_orient_matrix_UB_22      0.0629865000
_diffrn_orient_matrix_UB_23      0.0080436000
_diffrn_orient_matrix_UB_31      0.0053283000
_diffrn_orient_matrix_UB_32      0.0578910000
_diffrn_orient_matrix_UB_33      -0.0197486000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_unetI/netI     0.0656
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            2706
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         3.86
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.107
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27531
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark colourless'
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.68
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.738
_refine_diff_density_min         -0.758
_refine_diff_density_rms         0.120
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         1336
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0945
_refine_ls_R_factor_gt           0.0712
_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^)+(0.1245P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1841
_refine_ls_wR_factor_ref         0.2115
_reflns_number_gt                973
_reflns_number_total             1336
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol502431b_si_003.cif
_cod_data_source_block           a
_cod_depositor_comments
'Adding full bibliography for 1517829--1517830.cif.'
_cod_original_cell_volume        1318.13(14)
_cod_database_code               1517830
_reflns_odcompleteness_completeness 98.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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. Shared sites
{C7, N2}
3. Uiso/Uaniso restraints and constraints
Uanis(C7) = Uanis(N2)
4. Others
 Fixed Sof: Br1(0.5) C7(0.5) N2(0.5) C9(0.5) H9A(0.5) H9B(0.5) H9C(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
5.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;