Predicting the catalytic activity of azolium-based halogen bond donors: an experimentally-verified theoretical study.
Sysoeva, Alexandra A.; Novikov, Alexander S.; Il'in, Mikhail V.; Suslonov, Vitalii V.; Bolotin, Dmitrii S.; Organic & biomolecular chemistry 19 (2021) 7611–7620; doi:10.1039/d1ob01158h

data_7158207
_publ_section_title
;
 Predicting the catalytic activity of azolium-based halogen bond donors:
 an experimentally-verified theoretical study.
;
_journal_issue                   35
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7611
_journal_page_last               7620
_journal_paper_doi               10.1039/d1ob01158h
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C13 H14 F3 I N2 O3 S'
_chemical_formula_sum            'C13 H14 F3 I N2 O3 S'
_chemical_formula_weight         462.22
_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
_audit_creation_date             2021-05-24
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.01.05 svn.r3372 for Rigaku Oxford Diffraction, GUI svn.r5289)
;
_audit_update_record
;
2021-05-24 deposited with the CCDC.	2021-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.152(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3762(4)
_cell_length_b                   14.1584(7)
_cell_length_c                   14.0266(7)
_cell_measurement_reflns_used    11193
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.2960
_cell_measurement_theta_min      4.4530
_cell_volume                     1650.52(14)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -24.00  67.00   0.50    0.06    --   47.20 -71.00  69.00  182
  2  \w     39.00  85.00   0.50    0.22    --  107.75 -71.00  69.00   92
  3  \w     76.00 106.00   0.50    0.22    --  107.75 -77.00 120.00   60
  4  \w     45.00  71.00   0.50    0.22    --  107.75 -61.00   0.00   52
  5  \w     38.00  70.00   0.50    0.22    --  107.75 -61.00 -30.00   64
  6  \w     36.00  62.00   0.50    0.22    --  107.75 -61.00 -90.00   52
  7  \w     41.00  97.00   0.50    0.22    --  107.75 -94.00-150.00  112
  8  \w     76.00 104.00   0.50    0.22    --  107.75 -94.00-120.00   56
  9  \w     35.00  60.00   0.50    0.22    --  107.75 -61.00-120.00   50
 10  \w     35.00  69.00   0.50    0.22    --  107.75 -61.00-150.00   68
 11  \w    141.00 177.00   0.50    0.22    --  107.75  45.00 -30.00   72
 12  \w    116.00 165.00   0.50    0.22    --  107.75  71.00-159.00   98
 13  \w     95.00 135.00   0.50    0.22    --  107.75  45.00 -30.00   80
 14  \w     75.00 115.00   0.50    0.06    --   47.20 125.00  60.00   80
 15  \w     74.00 120.00   0.50    0.06    --   47.20 125.00  30.00   92
 16  \w    134.00 160.00   0.50    0.22    --  107.75  30.00 150.00   52
 17  \w     97.00 173.00   0.50    0.22    --  107.75  15.00 120.00  152
 18  \w     49.00  74.00   0.50    0.06    --   47.20  71.00-159.00   50
 19  \w     42.00  71.00   0.50    0.22    --  107.75 -61.00  90.00   58
 20  \w    -60.00   6.00   0.50    0.06    --  -47.20  71.00-159.00  132
 21  \w    -58.00 -33.00   0.50    0.22    -- -106.00  61.00-180.00   50
 22  \w    -72.00 -46.00   0.50    0.22    -- -106.00  71.00-159.00   52
 23  \w   -121.00 -93.00   0.50    0.22    -- -106.00 -15.00 -60.00   56
 24  \w    -71.00 -46.00   0.50    0.22    -- -106.00  61.00  30.00   50
 25  \w    -97.00 -35.00   0.50    0.22    -- -106.00  77.00 150.00  124
 26  \w    -95.00 -42.00   0.50    0.06    --  -47.20 -71.00  69.00  106
 27  \w   -129.00 -83.00   0.50    0.22    -- -106.00 -77.00 150.00   92
 28  \w   -162.00-132.00   0.50    0.22    -- -106.00 -71.00  69.00   60
 29  \w   -175.00-149.00   0.50    0.22    -- -106.00 -77.00 150.00   52
 30  \w   -177.00-130.00   0.50    0.22    -- -106.00 -15.00 -60.00   94
 31  \w   -177.00-107.00   0.50    0.22    -- -106.00 -30.00-120.00  140
 32  \w    -85.00 -40.00   0.50    0.22    -- -106.00  71.00-159.00   90
 33  \w   -120.00 -94.00   0.50    0.06    --  -47.20-125.00 -30.00   52
 34  \w    -20.00  16.00   0.50    0.06    --   47.20 -19.00 150.00   72
 35  \w    -27.00  10.00   0.50    0.06    --   47.20 -19.00  90.00   74
 36  \w     39.00  70.00   0.50    0.06    --   47.20  37.00 -30.00   62
 37  \w     75.00 119.00   0.50    0.06    --   47.20  37.00 -30.00   88
 38  \w   -172.00-145.00   0.50    0.22    -- -106.00 -77.00-180.00   54
 39  \w   -123.00 -97.00   0.50    0.22    -- -106.00 -15.00  60.00   52
 40  \w   -164.00-139.00   0.50    0.22    -- -106.00 -61.00 -30.00   50
 41  \w   -168.00-130.00   0.50    0.22    -- -106.00 -61.00   0.00   76
 42  \w   -120.00 -73.00   0.50    0.22    -- -106.00-125.00  30.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0042071000
_diffrn_orient_matrix_UB_12      0.0609425000
_diffrn_orient_matrix_UB_13      0.0912634000
_diffrn_orient_matrix_UB_21      0.1370209000
_diffrn_orient_matrix_UB_22      -0.0616779000
_diffrn_orient_matrix_UB_23      0.0501166000
_diffrn_orient_matrix_UB_31      0.1247031000
_diffrn_orient_matrix_UB_32      0.0657582000
_diffrn_orient_matrix_UB_33      -0.0376266000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16922
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.989
_diffrn_reflns_theta_min         4.455
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    16.867
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66263
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.860
_exptl_crystal_description       prism
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.612
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3129
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0252
_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^)+(0.0378P)^2^+0.9776P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0653
_refine_ls_wR_factor_ref         0.0659
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3031
_reflns_number_total             3129
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01158h2.cif
_cod_data_source_block           '[5]OTf'
_cod_depositor_comments
'Adding full bibliography for 7158206--7158208.cif.'
_cod_database_code               7158207
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C12 H10 N2 I1 S1 O3 F3'
_diffrn_oxdiff_digest_frames
;
01614d02cec8e7c926059f083e7597e60900089f093
;
_diffrn_oxdiff_digest_hkl
;
0171b188a8a7df1dd9fb761050663d8ed4e62c
;
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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:
 C6(H6), C8(H8), C7(H7), C9(H9), C10(H10)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              51056
_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 1.344
_oxdiff_exptl_absorpt_empirical_full_min 0.762