Copper(II)-Catalyzed Aerobic Oxidative Synthesis of Substituted 1,2,3- and 1,2,4-Triazoles from Bisarylhydrazones via C-H Functionalization/C-C/N-N/C-N Bonds Formation
Murali Mohan Guru; Tharmalingam Punniyamurthy; Journal of Organic Chemistry 77 (2012) 5063–5073; doi:10.1021/jo300592t

data_4027228
_publ_section_title
;
 Copper(II)-Catalyzed Aerobic Oxidative Synthesis of Substituted 1,2,3-
 and 1,2,4-Triazoles from Bisarylhydrazones via C-H
 Functionalization/C-C/N-N/C-N Bonds Formation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5063
_journal_page_last               5073
_journal_paper_doi               10.1021/jo300592t
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C20 H15 Cl2 N3 O'
_chemical_formula_weight         384.25
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8152(6)
_cell_length_b                   10.6246(5)
_cell_length_c                   17.8012(8)
_cell_measurement_temperature    298(2)
_cell_volume                     1856.35(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0431
_diffrn_reflns_av_sigmaI/netI    0.0409
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18741
_diffrn_reflns_theta_full        24.84
_diffrn_reflns_theta_max         24.84
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.363
_exptl_absorpt_correction_T_max  0.900
_exptl_absorpt_correction_T_min  0.877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADBAS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_description       block
_exptl_crystal_F_000             792.0
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.11(9)
_refine_ls_extinction_coef       0.0051(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.836
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3195
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      0.887
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0452
_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^)+(0.1000P)^2^+0.0200P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.1380
_reflns_number_gt                2075
_reflns_number_total             3195
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300592t_si_002.cif
_cod_data_source_block           1c''
_cod_original_cell_volume        1856.36(17)
_cod_database_code               4027228