Copper-catalyzed reactions of α,β-unsaturated N-tosylhydrazones with diaryliodonium salts to construct N-arylpyrazoles and diaryl sulfones
Chen, Lianmei; Zhou, Chuang; Li, Jing; Li, Jun; Guo, Xiaoqiang; Kang, Tai-Ran; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01338J

data_7158828
_publ_section_title
;
 Copper-catalyzed reactions of \a,\b-unsaturated N-tosylhydrazones with
 diaryliodonium salts to construct N-arylpyrazoles and diaryl sulfones
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01338J
_journal_year                    2022
_chemical_formula_moiety         'C16 H18 O2 S'
_chemical_formula_sum            'C16 H18 O2 S'
_chemical_formula_weight         274.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-11-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-04-17 deposited with the CCDC.	2022-08-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.298(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1266(3)
_cell_length_b                   24.3656(8)
_cell_length_c                   7.7718(2)
_cell_measurement_reflns_used    2609
_cell_measurement_temperature    295.13(10)
_cell_measurement_theta_max      72.4290
_cell_measurement_theta_min      6.0950
_cell_volume                     1443.33(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.13(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -53.00  31.00   1.00    1.20    --  -36.29  57.00 -30.00   84
  2  \w   -105.00 -17.00   1.00    1.20    --  -36.29 -38.00 -60.00   88
  3  \w     20.00 104.00   1.00    1.20    --   36.29  57.00 -90.00   84
  4  \w    -31.00  53.00   1.00    1.20    --   36.29 -57.00  90.00   84
  5  \w     23.00  90.00   1.00    1.20    --   36.29-125.00-180.00   67
  6  \w     39.00 115.00   1.00    4.81    --  108.71-111.00-180.00   76
  7  \w     91.00 176.00   1.00    4.81    --  108.71  61.00  60.00   85
  8  \w     91.00 176.00   1.00    4.81    --  108.71  61.00 -60.00   85
  9  \w     39.00 109.00   1.00    4.81    --  108.71 -94.00  60.00   70
 10  \w    100.00 178.00   1.00    4.81    --  108.71 111.00-120.00   78
 11  \w     39.00 130.00   1.00    4.81    --  108.71 -30.00 -60.00   91
 12  \w     42.00 127.00   1.00    4.81    --  108.71 -61.00 150.00   85
 13  \w   -105.00 -17.00   1.00    1.20    --  -36.29 -38.00  30.00   88
 14  \w    -53.00  31.00   1.00    1.20    --  -36.29  57.00  60.00   84
 15  \w     20.00 104.00   1.00    1.20    --   36.29  57.00-180.00   84
 16  \w     91.00 165.00   1.00    4.81    --  108.71  45.00 120.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0622227000
_diffrn_orient_matrix_UB_12      -0.0600352000
_diffrn_orient_matrix_UB_13      0.0086791000
_diffrn_orient_matrix_UB_21      0.1921031000
_diffrn_orient_matrix_UB_22      0.0195665000
_diffrn_orient_matrix_UB_23      0.0669866000
_diffrn_orient_matrix_UB_31      0.0071242000
_diffrn_orient_matrix_UB_32      -0.0039553000
_diffrn_orient_matrix_UB_33      0.2002460000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            8456
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.863
_diffrn_reflns_theta_min         3.628
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.948
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63561
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2802
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0556
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1100P)^2^+0.1447P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1556
_refine_ls_wR_factor_ref         0.1680
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2337
_reflns_number_total             2802
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01338j2.cif
_cod_data_source_block           cd-lj-4b
_cod_database_code               7158828
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C5(H5), C10(H10), C4(H4), C1(H1), C2(H2)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C7(H7A,H7B,H7C)
;
_shelx_res_checksum              27359
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.444
_oxdiff_exptl_absorpt_empirical_full_min 0.718