Halogen bonded associates of iodonium salts with 18-crown-6: does structural flexibility or structural rigidity of the σ-hole donor provide efficient substrate ligation?
Sysoeva, Alexandra A.; Novikov, Alexander S.; Il’in, Mikhail V.; Bolotin, Dmitrii S.; New Journal of Chemistry 48 (2024) 12929–12935; doi:10.1039/D4NJ02105C

data_7063283
_publ_section_title
;
 Halogen bonded associates of iodonium salts with 18-crown-6: does
 structural flexibility or structural rigidity of the \s-hole donor
 provide efficient substrate ligation?
;
_journal_issue                   29
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              12929
_journal_page_last               12935
_journal_paper_doi               10.1039/D4NJ02105C
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         '2(C12 H10 I), 2(C F3 O3 S), C12 H24 O6'
_chemical_formula_sum            'C38 H44 F6 I2 O12 S2'
_chemical_formula_weight         1124.65
_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     iterative
_audit_creation_date             2024-06-09
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2024-06-09 deposited with the CCDC.	2024-06-24 downloaded from the CCDC.
;
_cell_angle_alpha                89.682(2)
_cell_angle_beta                 88.449(2)
_cell_angle_gamma                63.993(2)
_cell_formula_units_Z            1
_cell_length_a                   9.5421(2)
_cell_length_b                   9.8378(2)
_cell_length_c                   12.7043(2)
_cell_measurement_reflns_used    10829
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.9340
_cell_measurement_theta_min      3.5020
_cell_volume                     1071.41(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_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    'olex2.solve 1.3 (Bourhis et al., 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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -50.00  15.00   0.50    0.30    --  -47.38  65.00 -25.00  130
  2  \w   -115.00 -53.00   0.50    0.30    --  -47.38 -65.00-161.00  124
  3  \w     -3.00  64.00   0.50    0.30    --   47.38 -65.00-161.00  134
  4  \w     49.00 119.00   0.50    0.30    --   47.38  65.00 -25.00  140
  5  \w   -169.00 -97.00   0.50    1.20    -- -106.00 -65.00-161.00  144
  6  \w    -76.00 -34.00   0.50    1.20    -- -106.00  65.00 -25.00   84
  7  \w     96.00 177.00   0.50    1.20    --  113.25  65.00 -25.00  162
  8  \w     42.00  76.00   0.50    1.20    --  113.25 -65.00-161.00   68
  9  \w     13.00  93.00   0.50    0.30    --   47.38-125.00-150.00  160
 10  \w     74.00 119.00   0.50    0.30    --   47.38 125.00-180.00   90
 11  \w     22.00  92.00   0.50    0.30    --   47.38-125.00  60.00  140
 12  \w    -77.00 -34.00   0.50    1.20    -- -106.00  77.00 150.00   86
 13  \w   -106.00 -79.00   0.50    1.20    -- -106.00 125.00  60.00   54
 14  \w    -86.00 -60.00   0.50    1.20    -- -106.00 145.00 103.91   52
 15  \w   -132.00 -75.00   0.50    1.20    -- -106.00 154.00 166.66  114
 16  \w   -125.00 -88.00   0.50    1.20    -- -106.00 145.00 103.91   74
 17  \w    -75.00 -45.00   0.50    1.20    -- -106.00 142.00-103.64   60
 18  \w   -124.00 -87.00   0.50    1.20    -- -106.00 142.00-103.64   74
 19  \w   -115.00 -83.00   0.50    1.20    -- -106.00 -94.00 -60.00   64
 20  \w    -69.00 -33.00   0.50    1.20    -- -106.00  61.00 120.00   72
 21  \w   -125.00 -52.00   0.50    1.20    -- -106.00 143.00 -67.37  146
 22  \w   -112.00 -53.00   0.50    1.20    -- -106.00 125.00   0.00  118
 23  \w   -176.00-125.00   0.50    1.20    -- -106.00 -94.00 -60.00  102
 24  \w   -120.00 -51.00   0.50    1.20    -- -106.00 136.00-152.10  138
 25  \w     42.00  70.00   0.50    1.20    --  113.25 -61.00 120.00   56
 26  \w     69.00  94.00   0.50    1.20    --  113.25 -77.00   0.00   50
 27  \w     51.00 102.00   0.50    1.20    --  113.25-125.00-120.00  102
 28  \w     81.00 106.00   0.50    1.20    --  113.25 -94.00 150.00   50
 29  \w     57.00  82.00   0.50    1.20    --  113.25-125.00  30.00   50
 30  \w     45.00  80.00   0.50    1.20    --  113.25 -94.00-180.00   70
 31  \w    110.00 178.00   0.50    1.20    --  113.25  61.00   0.00  136
 32  \w    134.00 160.00   0.50    1.20    --  113.25  30.00 150.00   52
 33  \w    120.00 176.00   0.50    1.20    --  113.25  61.00 -90.00  112
 34  \w    101.00 158.00   0.50    1.20    --  113.25  45.00 120.00  114
 35  \w     46.00  86.00   0.50    1.20    --  113.25 -94.00  90.00   80
 36  \w     42.00  67.00   0.50    1.20    --  113.25 -61.00-120.00   50
 37  \w    114.00 171.00   0.50    1.20    --  113.25  15.00  60.00  114
 38  \w     92.00 134.00   0.50    1.20    --  113.25-157.00-171.62   84
 39  \w    119.00 178.00   0.50    1.20    --  113.25  45.00-120.00  118
 40  \w     45.00  95.00   0.50    1.20    --  113.25 -94.00 -60.00  100
 41  \w     65.00 108.00   0.50    1.20    --  113.25-125.00  60.00   86
;
_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      0.0714369000
_diffrn_orient_matrix_UB_12      0.1130577000
_diffrn_orient_matrix_UB_13      0.0047925000
_diffrn_orient_matrix_UB_21      -0.1151271000
_diffrn_orient_matrix_UB_22      0.0855486000
_diffrn_orient_matrix_UB_23      0.0906657000
_diffrn_orient_matrix_UB_31      0.1180563000
_diffrn_orient_matrix_UB_32      -0.1012919000
_diffrn_orient_matrix_UB_33      0.0804545000
_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  0.0714
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11991
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        62.499
_diffrn_reflns_theta_max         62.499
_diffrn_reflns_theta_min         3.480
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    13.199
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.103a (Rigaku Oxford Diffraction, 2021)
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    1.743
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         3.147
_refine_diff_density_min         -1.410
_refine_diff_density_rms         0.169
_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     265
_refine_ls_number_reflns         3403
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0533
_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^)+(0.0870P)^2^+3.4464P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1390
_refine_ls_wR_factor_ref         0.1404
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3227
_reflns_number_total             3403
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj02105c3.cif
_cod_data_source_block           031-015_aas052
_cod_depositor_comments          'Adding full bibliography for 7063283.cif.'
_cod_database_code               7063283
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C25 H34 O9 S I F3'
_shelx_estimated_absorpt_t_max   0.693
_shelx_estimated_absorpt_t_min   0.458
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     73.11
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C4) = Uanis(C5)
3.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C16(H16A,H16B), C13(H13A,H13B), C14(H14A,H14B), C17(H17A,
 H17B), C15(H15A,H15B)
3.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C8(H8), C2(H2), C6(H6), C11(H11), C10(H10), C9(H9), C3(H3), C4(H4),
 C5(H5)
;
_shelx_res_checksum              60764
_shelx_hkl_checksum              2057
_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 2.619
_oxdiff_exptl_absorpt_empirical_full_min 0.380