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_7158827
_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         'C15 H11 Br N2'
_chemical_formula_sum            'C15 H11 Br N2'
_chemical_formula_weight         299.17
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-01-21
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2019-02-25 deposited with the CCDC.	2022-08-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.5406(3)
_cell_length_b                   8.3315(5)
_cell_length_c                   27.8631(12)
_cell_measurement_reflns_used    2560
_cell_measurement_temperature    292.95(10)
_cell_measurement_theta_max      71.3670
_cell_measurement_theta_min      4.7620
_cell_volume                     1286.20(12)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.95(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_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   -105.00 -17.00   1.00    1.00    --  -35.92 -38.00 150.00   88
  2  \w    -55.00  33.00   1.00    1.00    --  -35.92  38.00 -90.00   88
  3  \w    -33.00 105.00   1.00    1.00    --   35.92   0.00 150.00  138
  4  \w     25.00  91.00   1.00    1.00    --   35.92-127.00 -14.00   66
  5  \w    -31.00  53.00   1.00    1.00    --   35.92 -57.00  30.00   84
  6  \w     39.00 115.00   1.00    1.00    --  108.71-111.00  30.00   76
  7  \w    100.00 178.00   1.00    1.00    --  108.71 111.00 150.00   78
  8  \w     87.00 178.00   1.00    1.00    --  108.71  30.00-120.00   91
  9  \w    100.00 178.00   1.00    1.00    --  108.71 111.00 -30.00   78
 10  \w     39.00 130.00   1.00    1.00    --  108.71 -30.00-120.00   91
 11  \w    100.00 178.00   1.00    1.00    --  108.71 111.00-120.00   78
 12  \w     39.00 109.00   1.00    1.00    --  108.71 -94.00-180.00   70
 13  \w     39.00 109.00   1.00    1.00    --  108.71 -94.00 150.00   70
 14  \w     39.00 109.00   1.00    1.00    --  108.71 -94.00  60.00   70
 15  \w   -103.00 -19.00   1.00    1.00    --  -35.92 -57.00 -60.00   84
 16  \w    -31.00  51.00   1.00    1.00    --   35.92 -57.00 120.00   82
;
_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      0.0301740000
_diffrn_orient_matrix_UB_12      -0.0699766000
_diffrn_orient_matrix_UB_13      -0.0508318000
_diffrn_orient_matrix_UB_21      -0.0382502000
_diffrn_orient_matrix_UB_22      0.1682479000
_diffrn_orient_matrix_UB_23      -0.0216297000
_diffrn_orient_matrix_UB_31      0.2737620000
_diffrn_orient_matrix_UB_32      0.0311128000
_diffrn_orient_matrix_UB_33      0.0025870000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0656
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            7593
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.852
_diffrn_reflns_theta_min         5.542
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.199
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.09768
_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    1.545
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.175
_refine_diff_density_min         -1.178
_refine_diff_density_rms         0.121
_refine_ls_abs_structure_details
;
 Flack x determined using 528 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2447
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0804
_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^)+(0.1739P)^2^+0.1783P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2372
_refine_ls_wR_factor_ref         0.2596
_reflns_Friedel_coverage         0.612
_reflns_Friedel_fraction_full    0.927
_reflns_Friedel_fraction_max     0.898
_reflns_number_gt                1958
_reflns_number_total             2447
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01338j2.cif
_cod_data_source_block           ktr-3i
_cod_original_cell_volume        1286.21(12)
_cod_database_code               7158827
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7AA(H7AA), C8(H8), C4AA(H4AA), C2AA(H2AA), C6AA(H6AA), C1(H1), C2(H2),
 C3(H3), C4(H4), C5(H5), C6(H6)
;
_shelx_res_checksum              6574
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2019-01-15
_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 5.387
_oxdiff_exptl_absorpt_empirical_full_min 0.445