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_7158208
_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         'C7 H12 I1.5 N2, 0.5(I)'
_chemical_formula_sum            'C7 H12 I2 N2'
_chemical_formula_weight         377.99
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/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                 95.4830(12)
_cell_angle_gamma                90
_cell_formula_units_Z            24
_cell_length_a                   14.6499(2)
_cell_length_b                   16.45897(18)
_cell_length_c                   28.2119(4)
_cell_measurement_reflns_used    20202
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.3850
_cell_measurement_theta_min      3.1410
_cell_volume                     6771.39(15)
_computing_cell_refinement       'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.71a (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)'
_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 1.000
_diffrn_measured_fraction_theta_max 0.996
_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    -77.00 -40.00   0.50    0.41    --  -38.82 104.00  -9.00   74
  2  \w     20.00  51.00   0.50    0.41    --   38.82-104.00-110.00   62
  3  \w    106.00 132.00   0.50    1.63    --  100.00 104.00  -9.00   52
  4  \w     46.00 100.00   0.50    1.63    --  100.00-104.00-110.00  108
  5  \w   -111.00 -77.00   0.50    0.41    --  -38.82 -21.00 -90.00   68
  6  \w    -37.00   8.00   0.50    0.41    --  -38.82 104.00  -9.00   90
  7  \w    -73.00 -34.00   0.50    0.41    --  -38.82  11.00 150.00   78
  8  \w    -97.00 -19.00   0.50    0.41    --  -38.82 -65.00 -90.00  156
  9  \w    -20.00  36.00   0.50    0.41    --  -38.82  11.00 150.00  112
 10  \w    -73.00 -19.00   0.50    0.41    --  -38.82 -21.00 -90.00  108
 11  \w    -75.00 -13.00   0.50    0.41    --  -38.82 104.00  60.00  124
 12  \w     26.00  52.00   0.50    0.41    --   38.82  32.00-120.00   52
 13  \w     24.00  52.00   0.50    0.41    --   38.82-138.00 -30.00   56
 14  \w     62.00 107.00   0.50    0.41    --   38.82  32.00-120.00   90
 15  \w     61.00  86.00   0.50    0.41    --   38.82-138.00 -30.00   50
 16  \w     17.00  43.00   0.50    0.41    --   38.82 -32.00   0.00   52
 17  \w     27.00  52.00   0.50    0.41    --   38.82  32.00 -90.00   50
 18  \w    -25.00   0.00   0.50    0.41    --   38.82 -32.00   0.00   50
 19  \w     68.00 118.00   0.50    1.63    --  100.00 -53.00 -90.00  100
 20  \w     88.00 114.00   0.50    1.63    --  100.00  37.00  60.00   52
 21  \w     43.00  69.00   0.50    1.63    --  100.00 -30.00-150.00   52
 22  \w     26.00 105.00   0.50    1.63    --  100.00 -93.00 -90.00  158
 23  \w     35.00  85.00   0.50    1.63    --  100.00 -69.00 120.00  100
 24  \w    122.00 153.00   0.50    1.63    --  100.00  22.00 -90.00   62
 25  \w     37.00 118.00   0.50    1.63    --  100.00 -77.00 -90.00  162
 26  \w    110.00 147.00   0.50    1.63    --  100.00  61.00 150.00   74
 27  \w     82.00 118.00   0.50    1.63    --  100.00  22.00 -90.00   72
 28  \w     86.00 154.00   0.50    1.63    --  100.00  30.00 -30.00  136
 29  \w     90.00 117.00   0.50    1.63    --  100.00 -69.00 120.00   54
 30  \w     51.00 113.00   0.50    1.63    --  100.00 -30.00  30.00  124
 31  \w     60.00  85.00   0.50    1.63    --  100.00-111.00 -90.00   50
 32  \w    116.00 155.00   0.50    1.63    --  100.00  37.00  60.00   78
 33  \w     30.00  72.00   0.50    1.63    --  100.00 -93.00 -30.00   84
 34  \w    107.00 151.00   0.50    1.63    --  100.00 111.00   0.00   88
 35  \w    101.00 126.00   0.50    1.63    --  100.00  37.00 -60.00   50
 36  \w     88.00 151.00   0.50    1.63    --  100.00  30.00  30.00  126
 37  \w    129.00 156.00   0.50    1.63    --  100.00  77.00 120.00   54
 38  \w     47.00 121.00   0.50    1.63    --  100.00 -86.00  60.00  148
 39  \w     87.00 112.00   0.50    1.63    --  100.00 -30.00-150.00   50
 40  \w     87.00 113.00   0.50    1.63    --  100.00  22.00-180.00   52
 41  \w     30.00  55.00   0.50    1.63    --  100.00 -93.00  60.00   50
 42  \w    120.00 146.00   0.50    1.63    --  100.00 104.00  -9.00   52
 43  \w    -15.00  28.00   0.50    0.41    --  -38.82  32.00-120.00   86
 44  \w    -57.00  -6.00   0.50    0.41    --  -38.82  21.00   0.00  102
 45  \w    -49.00  21.00   0.50    0.41    --  -38.82  32.00   0.00  140
 46  \w    -59.00  16.00   0.50    0.41    --  -38.82  54.00   0.00  150
 47  \w     26.00  74.00   0.50    0.41    --   38.82  32.00-180.00   96
 48  \w     46.00  98.00   0.50    0.41    --   38.82  54.00-180.00  104
 49  \w     27.00  85.00   0.50    0.41    --   38.82  65.00  90.00  116
 50  \w     48.00  73.00   0.50    0.41    --   38.82-138.00  30.00   50
 51  \w     68.00  94.00   0.50    1.63    --  100.00 -22.00-180.00   52
 52  \w     86.00 111.00   0.50    1.63    --  100.00  37.00 -60.00   50
 53  \w     99.00 137.00   0.50    1.63    --  100.00 111.00  60.00   76
 54  \w     84.00 117.00   0.50    1.63    --  100.00  93.00-150.00   66
 55  \w    120.00 145.00   0.50    1.63    --  100.00  93.00-150.00   50
 56  \w     44.00  73.00   0.50    1.63    --  100.00 -45.00-120.00   58
 57  \w     39.00  65.00   0.50    1.63    --  100.00 -22.00-180.00   52
 58  \w     82.00 139.00   0.50    1.63    --  100.00  69.00  60.00  114
 59  \w    104.00 130.00   0.50    1.63    --  100.00  37.00 -30.00   52
 60  \w     82.00 108.00   0.50    1.63    --  100.00-111.00-120.00   52
 61  \w     39.00  69.00   0.50    1.63    --  100.00-133.00  90.00   60
 62  \w     82.00 108.00   0.50    1.63    --  100.00-111.00 -30.00   52
 63  \w     39.00  64.00   0.50    1.63    --  100.00-133.00  60.00   50
 64  \w     91.00 117.00   0.50    1.63    --  100.00-133.00  60.00   52
 65  \w     63.00  89.00   0.50    1.63    --  100.00 -77.00-180.00   52
 66  \w    132.00 157.00   0.50    1.63    --  100.00  37.00 -60.00   50
 67  \w     46.00  72.00   0.50    1.63    --  100.00 -22.00  90.00   52
 68  \w     33.00  59.00   0.50    1.63    --  100.00-111.00-120.00   52
 69  \w     57.00 104.00   0.50    1.63    --  100.00-111.00 -60.00   94
 70  \w    131.00 156.00   0.50    1.63    --  100.00  61.00  30.00   50
 71  \w     92.00 117.00   0.50    1.63    --  100.00-133.00 150.00   50
 72  \w     50.00  83.00   0.50    1.63    --  100.00 -86.00  90.00   66
 73  \w    126.00 155.00   0.50    1.63    --  100.00  30.00   0.00   58
 74  \w    127.00 152.00   0.50    1.63    --  100.00  30.00 150.00   50
 75  \w     79.00 120.00   0.50    1.63    --  100.00 -69.00 -30.00   82
 76  \w     58.00  94.00   0.50    1.63    --  100.00 -37.00 -90.00   72
 77  \w     88.00 114.00   0.50    1.63    --  100.00 -86.00  90.00   52
 78  \w     30.00  73.00   0.50    1.63    --  100.00 -15.00-150.00   86
 79  \w    108.00 150.00   0.50    1.63    --  100.00   0.00 -90.00   84
 80  \w     99.00 125.00   0.50    1.63    --  100.00  30.00  60.00   52
 81  \w     90.00 155.00   0.50    1.63    --  100.00  45.00 120.00  130
 82  \w    125.00 151.00   0.50    1.63    --  100.00  77.00 -90.00   52
 83  \w     93.00 118.00   0.50    1.63    --  100.00  30.00   0.00   50
 84  \w     58.00 108.00   0.50    1.63    --  100.00-111.00  60.00  100
 85  \w     80.00 107.00   0.50    1.63    --  100.00-111.00 150.00   54
 86  \w     66.00  91.00   0.50    1.63    --  100.00 -93.00-150.00   50
 87  \w     59.00 116.00   0.50    1.63    --  100.00-133.00-120.00  114
 88  \w     49.00  75.00   0.50    1.63    --  100.00-133.00 -60.00   52
;
_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      -0.0627733000
_diffrn_orient_matrix_UB_12      0.0450233000
_diffrn_orient_matrix_UB_13      -0.0383297000
_diffrn_orient_matrix_UB_21      -0.0091202000
_diffrn_orient_matrix_UB_22      -0.0781519000
_diffrn_orient_matrix_UB_23      -0.0301376000
_diffrn_orient_matrix_UB_31      -0.0844961000
_diffrn_orient_matrix_UB_32      -0.0249531000
_diffrn_orient_matrix_UB_33      0.0251371000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1082
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            38003
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.514
_diffrn_reflns_theta_min         3.147
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    43.377
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.19820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.71a (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    2.225
_exptl_crystal_description       prism
_exptl_crystal_F_000             4176
_exptl_crystal_size_max          0.301
_exptl_crystal_size_mid          0.191
_exptl_crystal_size_min          0.093
_refine_diff_density_max         1.665
_refine_diff_density_min         -0.885
_refine_diff_density_rms         0.237
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         6461
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0423
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0775P)^2^+14.5671P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1154
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6050
_reflns_number_total             6461
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01158h2.cif
_cod_data_source_block           '[1]I'
_cod_depositor_comments
'Adding full bibliography for 7158206--7158208.cif.'
_cod_original_cell_volume        6771.38(15)
_cod_database_code               7158208
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C6 H4 N2 I '
_shelx_estimated_absorpt_t_max   0.107
_shelx_estimated_absorpt_t_min   0.027
_diffrn_oxdiff_ac3_digest_frames
;
01951637aee7cc68ba2f7477df929e8e5c000314702
;
_diffrn_oxdiff_ac3_digest_hkl
;
0163ac52addfa025579cc70738bb45d94cd6e0
;
_reflns_odcompleteness_completeness 98.49
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C4(H4A,H4B,H4C), C4B(H4BA,H4BB,H4BC), C7A(H7AA,H7AB,H7AC),
 C4A(H4AA,H4AB,H4AC), C5A(H5AA,H5AB,H5AC), C6A(H6AA,H6AB,H6AC), C6(H6A,H6B,H6C),
  C7B(H7BA,H7BB,H7BC), C5(H5A,H5B,H5C), C6B(H6BA,H6BB,H6BC), C5B(H5BA,H5BB,H5BC)
;
_shelx_res_checksum              42606
_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 2.740
_oxdiff_exptl_absorpt_empirical_full_min 0.410