Copper-catalyzed tandem cyclization/arylation of α,β-alkynic hydrazones with diaryliodonium salts: synthesis of <i>N</i>-arylpyrazoles.
Parida, Sushanta Kumar; Joshi, Saurav; Murarka, Sandip; Organic & biomolecular chemistry 21 (2023) 5784–5789; doi:10.1039/d3ob00899a

data_7159446
_publ_section_title
;
 Copper-catalyzed tandem cyclization/arylation of &#x3b1;,&#x3b2;-alkynic
 hydrazones with diaryliodonium salts: synthesis of
 <i>N</i>-arylpyrazoles.
;
_journal_issue                   28
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5784
_journal_page_last               5789
_journal_paper_doi               10.1039/d3ob00899a
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C21 H15 Br N2'
_chemical_formula_sum            'C21 H15 Br N2'
_chemical_formula_weight         375.26
_chemical_name_systematic        SKP-02
_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     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2fwtcj
_audit_creation_date             2023-05-06
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-06-07 deposited with the CCDC.	2023-07-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.177(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9325(5)
_cell_length_b                   16.9864(7)
_cell_length_c                   9.6085(5)
_cell_measurement_reflns_used    8066
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.1490
_cell_measurement_theta_min      3.9050
_cell_volume                     1695.29(15)
_computing_cell_refinement       'CrysAlisPro 1.171.42.52a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.52a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.52a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.811
_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     26.00  60.00   0.50   17.49    --   -4.14  44.00 158.00   68
  2  \w     -6.00  22.00   0.50   17.49    --   -4.14  44.00 158.00   56
  3  \w    -41.00  -8.00   0.50   17.49    --    3.51 -77.00 150.00   66
  4  \w      1.00  55.00   0.50   17.49    --    3.51  37.00   0.00  108
  5  \w    -15.00  10.00   0.50   17.49    --    3.51 -99.00 -60.00   50
  6  \w     -9.00  32.00   0.50   17.49    --   -4.14 -99.00  60.00   82
  7  \w    -29.00  16.00   0.50   17.49    --   -4.14 -77.00 -60.00   90
  8  \w    -69.00  -9.00   0.50   17.49    --   -4.14 -44.00   7.00  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0599612000
_diffrn_orient_matrix_UB_12      0.0026988000
_diffrn_orient_matrix_UB_13      0.0563103000
_diffrn_orient_matrix_UB_21      -0.0292682000
_diffrn_orient_matrix_UB_22      0.0227456000
_diffrn_orient_matrix_UB_23      0.0428142000
_diffrn_orient_matrix_UB_31      -0.0144331000
_diffrn_orient_matrix_UB_32      -0.0348995000
_diffrn_orient_matrix_UB_33      0.0322737000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.811
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16688
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.811
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.284
_diffrn_reflns_theta_min         3.605
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.428
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51347
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.52a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.828
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4120
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.828
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0321
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1067
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3454
_reflns_number_total             4120
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00899a2.cif
_cod_data_source_block           pa-1_auto
_cod_depositor_comments          'Adding full bibliography for 7159446.cif.'
_cod_original_cell_volume        1695.29(14)
_cod_database_code               7159446
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N Br'
_shelx_estimated_absorpt_t_max   0.642
_shelx_estimated_absorpt_t_min   0.642
_reflns_odcompleteness_completeness 99.50
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C006(H006), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F),
 C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N), C00O(H00O)
;
_shelx_res_checksum              53481
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.517
_oxdiff_exptl_absorpt_empirical_full_min 0.600