I₂-TBHP-catalyzed oxidative cross-coupling of N-sulfonyl hydrazones and isocyanides to 5-aminopyrazoles.
Senadi, Gopal Chandru; Hu, Wan-Ping; Lu, Ting-Yi; Garkhedkar, Amol Milind; Vandavasi, Jaya Kishore; Wang, Jeh-Jeng; Organic letters 17 (2015) 1521–1524; doi:10.1021/acs.orglett.5b00398

data_1554842
_publ_section_title
;
 I&#x2082;-TBHP-catalyzed oxidative cross-coupling of N-sulfonyl
 hydrazones and isocyanides to 5-aminopyrazoles.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1521
_journal_page_last               1524
_journal_paper_doi               10.1021/acs.orglett.5b00398
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C22 H18 F N3 O2 S'
_chemical_formula_sum            'C22 H18 F N3 O2 S'
_chemical_formula_weight         407.45
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 100.958(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.7629(8)
_cell_length_b                   11.6907(5)
_cell_length_c                   10.7408(7)
_cell_measurement_reflns_used    2306
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      27.9160
_cell_measurement_theta_min      3.4280
_cell_volume                     1943.22(18)
_computing_cell_refinement
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_collection
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.842
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0574
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9109
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.44
_diffrn_reflns_theta_min         2.74
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97314
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) 
(compiled Jan 14 2014,18:38:05) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4530
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0536
_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^)+(0.0621P)^2^+0.2516P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1244
_refine_ls_wR_factor_ref         0.1418
_reflns_number_gt                3207
_reflns_number_total             4530
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b00398_si_003.cif
_cod_data_source_block           cjfisof
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1554842