Regioselective one-pot, three-component synthesis of substituted 2H-indazoles from nitroarylaldehyde, alkyne and amine catalyzed by CuBr/Zn(OTf)2 system
Saikia, Anil; Unnava, Ramanjaneyulu; Indukuri, Kiran; Sarkar, Sujit; RSC Adv.  (2014) –; doi:10.1039/C4RA10093J

data_7218579
_publ_section_title
;
 Regioselective one-pot, three-component synthesis of substituted
 2H-indazoles from nitroarylaldehyde, alkyne and amine catalyzed by
 CuBr/Zn(OTf)2 system
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA10093J
_journal_year                    2014
_chemical_formula_sum            'C25 H22 N2 O2'
_chemical_formula_weight         382.45
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 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                   5.1346(2)
_cell_length_b                   15.0120(4)
_cell_length_c                   26.4598(7)
_cell_measurement_temperature    296(2)
_cell_volume                     2039.54(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 100.00
_diffrn_measured_fraction_theta_max 100.00
_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  0.1192
_diffrn_reflns_av_sigmaI/netI    0.0493
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12770
_diffrn_reflns_theta_full        26.48
_diffrn_reflns_theta_max         26.48
_diffrn_reflns_theta_min         1.54
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.2454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.083
_refine_diff_density_min         -0.119
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.747
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         2471
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.747
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0345
_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^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0932
_reflns_number_gt                1546
_reflns_number_total             2471
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra10093j2.cif
_cod_data_source_block           123
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               7218579