Base-mediated intramolecular aryl–aryl coupling in pyrazolyl-containing iodolium salts
Safinskaya, Yana V.; Il’in, Mikhail V.; Bolotin, Dmitrii S.; New Journal of Chemistry 48 (2024) 19034–19039; doi:10.1039/D4NJ02894E

data_7063516
_publ_section_title
;
 Base-mediated intramolecular aryl--aryl coupling in pyrazolyl-containing
 iodolium salts
;
_journal_issue                   45
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              19034
_journal_page_last               19039
_journal_paper_doi               10.1039/D4NJ02894E
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C16 H13 I N2, 2(C F3 O3 S)'
_chemical_formula_sum            'C18 H13 F6 I N2 O6 S2'
_chemical_formula_weight         658.32
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2k14vm
_audit_creation_date             2024-05-07
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2024-05-10 deposited with the CCDC.	2024-11-04 downloaded from the CCDC.
;
_cell_angle_alpha                64.339(4)
_cell_angle_beta                 84.268(3)
_cell_angle_gamma                83.514(4)
_cell_formula_units_Z            2
_cell_length_a                   9.9399(5)
_cell_length_b                   10.6305(5)
_cell_length_c                   11.8378(4)
_cell_measurement_reflns_used    6626
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.3590
_cell_measurement_theta_min      4.1270
_cell_volume                     1118.45(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_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   -103.00 -46.00   0.50    3.00    --  -41.22 -48.00 147.00  114
  2  \w    -39.00  18.00   0.50    3.00    --  -41.22  48.00 -63.00  114
  3  \w     32.00  82.00   0.50    3.00    --   41.22  48.00 -63.00  100
  4  \w     65.00 112.00   0.50   12.00    --  100.00 -48.00 147.00   94
  5  \w    115.00 141.00   0.50   12.00    --  100.00  48.00 -63.00   52
  6  \w     86.00 112.00   0.50   12.00    --  100.00  48.00 -63.00   52
  7  \w    -63.00 -33.00   0.50    3.00    --  -41.22 -21.00  30.00   60
  8  \w   -100.00 -36.00   0.50    3.00    --  -41.22 -43.00-180.00  128
  9  \w   -111.00 -68.00   0.50    3.00    --  -41.22 -21.00  30.00   86
 10  \w    -96.00 -14.00   0.50    3.00    --  -41.22 138.00  30.00  164
 11  \w     14.00  41.00   0.50    3.00    --   41.22 -43.00  90.00   54
 12  \w     21.00  47.00   0.50    3.00    --   41.22 -43.00 -60.00   52
 13  \w    -19.00   7.00   0.50    3.00    --   41.22 -43.00 -60.00   52
 14  \w     36.00  62.00   0.50    3.00    --   41.22  32.00 -90.00   52
 15  \w    -15.00  39.00   0.50    3.00    --   41.22 -54.00  30.00  108
 16  \w    -21.00   9.00   0.50    3.00    --   41.22 -43.00  90.00   60
 17  \w     32.00  84.00   0.50    3.00    --   41.22-138.00 -90.00  104
 18  \w     19.00  96.00   0.50    3.00    --   41.22-138.00  30.00  154
 19  \w     -8.00  18.00   0.50    3.00    --   41.22 -48.00 147.00   52
 20  \w     30.00  56.00   0.50    3.00    --   41.22 -54.00 -30.00   52
 21  \w     78.00 104.00   0.50    3.00    --   41.22  32.00 -90.00   52
 22  \w    -16.00   9.00   0.50    3.00    --   41.22 -54.00 -30.00   50
 23  \w     40.00  89.00   0.50    3.00    --   41.22  32.00 150.00   98
 24  \w     32.00  96.00   0.50   12.00    --  100.00 -93.00  60.00  128
 25  \w     87.00 145.00   0.50   12.00    --  100.00  50.00 120.00  116
 26  \w     91.00 124.00   0.50   12.00    --  100.00  25.00   0.00   66
 27  \w     56.00 107.00   0.50   12.00    --  100.00-111.00 -30.00  102
 28  \w     37.00  92.00   0.50   12.00    --  100.00-111.00  60.00  110
 29  \w     95.00 153.00   0.50   12.00    --  100.00  42.00 -90.00  116
 30  \w     53.00  92.00   0.50   12.00    --  100.00 -25.00  90.00   78
 31  \w     72.00 108.00   0.50   12.00    --  100.00-111.00  30.00   72
 32  \w     61.00  87.00   0.50   12.00    --  100.00-133.00   0.00   52
 33  \w     53.00 109.00   0.50   12.00    --  100.00 -33.00  90.00  112
 34  \w     97.00 136.00   0.50   12.00    --  100.00  33.00 150.00   78
 35  \w     88.00 128.00   0.50   12.00    --  100.00  42.00-120.00   80
 36  \w     64.00 109.00   0.50   12.00    --  100.00-133.00 -90.00   90
 37  \w     58.00 105.00   0.50   12.00    --  100.00 -25.00 -60.00   94
 38  \w    132.00 157.00   0.50   12.00    --  100.00  25.00 -30.00   50
 39  \w    114.00 154.00   0.50   12.00    --  100.00  77.00 150.00   80
 40  \w     37.00 109.00   0.50   12.00    --  100.00 -50.00 -90.00  144
 41  \w    110.00 144.00   0.50   12.00    --  100.00   8.00  90.00   68
 42  \w     79.00 117.00   0.50   12.00    --  100.00-133.00-180.00   76
 43  \w     39.00 122.00   0.50   12.00    --  100.00 -68.00  60.00  166
 44  \w     43.00 113.00   0.50   12.00    --  100.00 -42.00  30.00  140
 45  \w     79.00 104.00   0.50   12.00    --  100.00-111.00-180.00   50
 46  \w     94.00 137.00   0.50   12.00    --  100.00  33.00  90.00   86
 47  \w     85.00 156.00   0.50   12.00    --  100.00  50.00   0.00  142
 48  \w     40.00  65.00   0.50   12.00    --  100.00 -77.00-180.00   50
 49  \w     89.00 118.00   0.50   12.00    --  100.00 -59.00-180.00   58
 50  \w     91.00 119.00   0.50   12.00    --  100.00  25.00 -30.00   56
 51  \w     37.00 104.00   0.50   12.00    --  100.00-111.00 -60.00  134
 52  \w     52.00 117.00   0.50   12.00    --  100.00-133.00 -60.00  130
 53  \w     50.00  75.00   0.50   12.00    --  100.00 178.00 -60.00   50
 54  \w    113.00 144.00   0.50   12.00    --  100.00 178.00 -60.00   62
 55  \w    128.00 154.00   0.50   12.00    --  100.00  33.00-150.00   52
 56  \w    119.00 145.00   0.50   12.00    --  100.00  17.00 120.00   52
 57  \w     44.00  73.00   0.50   12.00    --  100.00 -59.00-180.00   58
 58  \w     72.00 112.00   0.50   12.00    --  100.00 -59.00 -30.00   80
 59  \w     82.00 107.00   0.50   12.00    --  100.00-111.00  90.00   50
 60  \w     86.00 111.00   0.50   12.00    --  100.00  93.00 -90.00   50
 61  \w    130.00 155.00   0.50   12.00    --  100.00  25.00   0.00   50
 62  \w     37.00  62.00   0.50   12.00    --  100.00-111.00-180.00   50
 63  \w     75.00 100.00   0.50   12.00    --  100.00 -68.00 -30.00   50
 64  \w     34.00  85.00   0.50   12.00    --  100.00 -87.00 -30.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1038513000
_diffrn_orient_matrix_UB_12      0.1110300000
_diffrn_orient_matrix_UB_13      -0.0627917000
_diffrn_orient_matrix_UB_21      0.0803758000
_diffrn_orient_matrix_UB_22      -0.0926460000
_diffrn_orient_matrix_UB_23      -0.0578083000
_diffrn_orient_matrix_UB_31      -0.0846474000
_diffrn_orient_matrix_UB_32      0.0713821000
_diffrn_orient_matrix_UB_33      -0.1167408000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0809
_diffrn_reflns_av_unetI/netI     0.0667
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9126
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        62.491
_diffrn_reflns_theta_max         62.491
_diffrn_reflns_theta_min         4.150
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    13.845
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67259
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.101a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.955
_exptl_crystal_description       prism
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         2.703
_refine_diff_density_min         -2.300
_refine_diff_density_rms         0.263
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.205
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         3519
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.205
_refine_ls_R_factor_all          0.1002
_refine_ls_R_factor_gt           0.0850
_refine_ls_shift/su_max          0.071
_refine_ls_shift/su_mean         0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1875P)^2^+5.5888P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2504
_refine_ls_wR_factor_ref         0.2881
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2939
_reflns_number_total             3519
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj02894e2.cif
_cod_data_source_block           031-007_syv144_me2co
_cod_depositor_comments          'Adding full bibliography for 7063516.cif.'
_cod_database_code               7063516
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C14 H12 N2 I S O3 F3'
_shelx_estimated_absorpt_t_max   0.681
_shelx_estimated_absorpt_t_min   0.404
_reflns_odcompleteness_completeness 96.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_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. Uiso/Uaniso restraints and constraints
Uanis(C10) = Uanis(C5)
Uanis(C10) = Uanis(C3)
3.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C12(H12), C7(H7), C16(H16), C8(H8), C15(H15), C2(H2), C14(H14),
 C13(H13), C9(H9)
3.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              12428
_shelx_hkl_checksum              54851
_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 3.973
_oxdiff_exptl_absorpt_empirical_full_min 0.245