Zwitterionic iodonium species afford halogen bond-based porous organic frameworks
Soldatova, Natalia S.; Postnikov, Pavel S.; Ivanov, Daniil M.; Semyonov, Oleg V.; Kukurina, Olga S.; Guselnikova, Olga; Yamauchi, Yusuke; Wirth, Thomas; Zhdankin, Viktor V.; Yusubov, Mekhman S.; Gomila, Rosa M.; Frontera, Antonio; Resnati, Giuseppe; Kukushkin, Vadim Yu.; Chemical Science  (2022) –; doi:10.1039/D2SC00892K

data_1566878
_publ_section_title
;
 Zwitterionic iodonium species afford halogen bond-based porous organic
 frameworks
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC00892K
_journal_year                    2022
_chemical_formula_moiety         'C12 H8 Cl I O3 S'
_chemical_formula_sum            'C12 H8 Cl I O3 S'
_chemical_formula_weight         394.59
_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_creation_date             2020-08-31
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2021-07-13 deposited with the CCDC.	2022-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                94.9610(10)
_cell_angle_beta                 93.9970(10)
_cell_angle_gamma                91.8580(10)
_cell_formula_units_Z            4
_cell_length_a                   6.09810(10)
_cell_length_b                   8.11370(10)
_cell_length_c                   25.8853(3)
_cell_measurement_reflns_used    11999
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.2180
_cell_measurement_theta_min      3.4290
_cell_volume                     1271.90(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_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                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.997
_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    -30.00   5.00   0.50    1.20    --  -38.82 115.00  11.00   70
  2  \w    -84.00 -50.00   0.50    1.20    --  -38.82-167.00 136.00   68
  3  \w   -110.00 -74.00   0.50    1.20    --  -38.82 167.00 156.00   72
  4  \w     61.00  86.00   0.50    1.20    --   38.82 167.00 156.00   50
  5  \w     21.00  46.00   0.50    1.20    --   38.82-115.00 -78.00   50
  6  \w     74.00 105.00   0.50    1.20    --   38.82-167.00 136.00   62
  7  \w     71.00  96.00   0.50    0.20    --  100.00-115.00 -78.00   50
  8  \w    104.00 140.00   0.50    0.20    --  100.00-167.00 136.00   72
  9  \w     77.00 102.00   0.50    0.20    --  100.00 167.00 156.00   50
 10  \w     84.00 110.00   0.50    0.20    --  100.00 115.00  11.00   52
 11  \w    -57.00 -31.00   0.50    1.20    --  -38.82 -32.00-120.00   52
 12  \w    -53.00  14.00   0.50    1.20    --  -38.82  43.00  30.00  134
 13  \w    -81.00 -55.00   0.50    1.20    --  -38.82 138.00   0.00   52
 14  \w   -106.00 -61.00   0.50    1.20    --  -38.82 -32.00-120.00   90
 15  \w   -107.00 -27.00   0.50    1.20    --  -38.82 -32.00  60.00  160
 16  \w    -46.00 -21.00   0.50    1.20    --  -38.82 138.00   0.00   50
 17  \w     70.00  96.00   0.50    1.20    --   38.82-138.00-180.00   52
 18  \w     36.00  75.00   0.50    1.20    --   38.82-104.00-180.00   78
 19  \w     17.00 103.00   0.50    1.20    --   38.82  65.00-180.00  172
 20  \w      4.00  30.00   0.50    1.20    --   38.82-104.00-180.00   52
 21  \w     39.00 102.00   0.50    1.20    --   38.82  43.00-120.00  126
 22  \w     18.00  61.00   0.50    1.20    --   38.82-138.00-180.00   86
 23  \w     29.00  57.00   0.50    1.20    --   38.82 -21.00 -60.00   56
 24  \w     27.00 105.00   0.50    1.20    --   38.82  43.00 -30.00  156
 25  \w     -6.00  20.00   0.50    1.20    --   38.82 -21.00 -60.00   52
 26  \w      7.00  33.00   0.50    1.20    --   38.82 -43.00  60.00   52
 27  \w     34.00  78.00   0.50    0.20    --  100.00 -37.00-180.00   88
 28  \w     38.00 115.00   0.50    0.20    --  100.00-133.00-120.00  154
 29  \w     60.00 106.00   0.50    0.20    --  100.00 -30.00  60.00   92
 30  \w     53.00 115.00   0.50    0.20    --  100.00 -37.00 -60.00  124
 31  \w     92.00 154.00   0.50    0.20    --  100.00  30.00 -90.00  124
 32  \w     28.00 114.00   0.50    0.20    --  100.00 -22.00  30.00  172
 33  \w     71.00 122.00   0.50    0.20    --  100.00 133.00 -30.00  102
 34  \w     55.00  81.00   0.50    0.20    --  100.00 -86.00-180.00   52
 35  \w     52.00 100.00   0.50    0.20    --  100.00-111.00 -60.00   96
 36  \w     71.00  97.00   0.50    0.20    --  100.00 -72.00 -99.90   52
 37  \w     38.00 120.00   0.50    0.20    --  100.00 -53.00-120.00  164
 38  \w     78.00 104.00   0.50    0.20    --  100.00  69.00 120.00   52
 39  \w    126.00 152.00   0.50    0.20    --  100.00  69.00 120.00   52
 40  \w     65.00 105.00   0.50    0.20    --  100.00 -93.00 -60.00   80
 41  \w     93.00 119.00   0.50    0.20    --  100.00  45.00 -30.00   52
 42  \w     82.00 135.00   0.50    0.20    --  100.00 111.00-180.00  106
 43  \w     89.00 121.00   0.50    0.20    --  100.00 -69.00   0.00   64
 44  \w     94.00 119.00   0.50    0.20    --  100.00 -69.00-120.00   50
 45  \w     88.00 115.00   0.50    0.20    --  100.00  37.00 -30.00   54
 46  \w     42.00 106.00   0.50    0.20    --  100.00 -93.00  90.00  128
 47  \w     42.00  67.00   0.50    0.20    --  100.00 -69.00-120.00   50
 48  \w     77.00 115.00   0.50    0.20    --  100.00 -37.00  90.00   76
 49  \w     85.00 119.00   0.50    0.20    --  100.00-133.00 120.00   68
 50  \w     42.00  83.00   0.50    0.20    --  100.00 -69.00   0.00   82
 51  \w     97.00 125.00   0.50    0.20    --  100.00 -77.00 -90.00   56
 52  \w    105.00 149.00   0.50    0.20    --  100.00 111.00-150.00   88
 53  \w     48.00  74.00   0.50    0.20    --  100.00 -37.00  90.00   52
 54  \w    125.00 157.00   0.50    0.20    --  100.00  45.00 -30.00   64
 55  \w     41.00  66.00   0.50    0.20    --  100.00-133.00 120.00   50
 56  \w     59.00  85.00   0.50    0.20    --  100.00-111.00-180.00   52
 57  \w     82.00 108.00   0.50    0.20    --  100.00 -37.00-180.00   52
 58  \w     50.00  78.00   0.50    0.20    --  100.00-111.00-120.00   56
 59  \w     82.00 109.00   0.50    0.20    --  100.00-111.00-120.00   54
 60  \w     32.00  78.00   0.50    0.20    --  100.00 -15.00 -90.00   92
 61  \w     89.00 149.00   0.50    0.20    --  100.00  37.00   0.00  120
 62  \w     27.00  74.00   0.50    0.20    --  100.00 -93.00-120.00   94
 63  \w     56.00 117.00   0.50    0.20    --  100.00 -61.00  60.00  122
 64  \w     89.00 153.00   0.50    0.20    --  100.00  30.00 -60.00  128
 65  \w     94.00 119.00   0.50    0.20    --  100.00 115.00  11.00   50
 66  \w    -40.00 -14.00   0.50    1.20    --    0.00 119.00 144.65   52
 67  \w    -23.00   8.00   0.50    1.20    --   20.00 112.00 -86.98   62
 68  \w    -10.00  15.00   0.50    1.20    --   28.00 104.00  90.68   50
 69  \w     -1.00  24.00   0.50    1.20    --   32.00  94.00  -4.17   50
 70  \w      5.00  30.00   0.50    1.20    --   36.00  89.00-150.72   50
 71  \w    -37.00 -11.00   0.50    1.20    --  -38.82 104.00 150.00   52
 72  \w     11.00  36.00   0.50    1.20    --   40.00  84.00  88.99   50
 73  \w     11.00  36.00   0.50    1.20    --   40.00  83.00 -29.47   50
 74  \w     16.00  41.00   0.50    1.20    --   44.00  80.00 158.19   50
 75  \w     17.00  42.00   0.50    1.20    --   44.00  79.00 -96.52   50
 76  \w     16.00  41.00   0.50    1.20    --   44.00  81.00  43.43   50
 77  \w     16.00  41.00   0.50    1.20    --   44.00  81.00 128.12   50
 78  \w     16.00  41.00   0.50    1.20    --   44.00  81.00 112.57   50
 79  \w     17.00  42.00   0.50    1.20    --   44.00  79.00-130.98   50
 80  \w     22.00  48.00   0.50    1.20    --   48.00  74.00 -68.84   52
 81  \w     89.00 114.00   0.50    1.20    --   48.00  74.00 -68.84   50
 82  \w     26.00  52.00   0.50    1.20    --   48.00  71.00 -12.54   52
 83  \w     86.00 112.00   0.50    1.20    --   48.00  71.00 -12.54   52
 84  \w     33.00  59.00   0.50    1.20    --   52.00  75.00   2.60   52
 85  \w     26.00  51.00   0.50    1.20    --   52.00  76.00-173.51   50
 86  \w     75.00 101.00   0.50    1.20    --   52.00  76.00 119.61   52
 87  \w     83.00 108.00   0.50    1.20    --   52.00  77.00 -55.04   50
 88  \w     27.00  53.00   0.50    1.20    --   52.00  76.00 119.61   52
 89  \w     29.00  55.00   0.50    1.20    --   52.00  77.00 -55.04   52
 90  \w     33.00  59.00   0.50    1.20    --   56.00  76.00-116.70   52
 91  \w     79.00 105.00   0.50    1.20    --   56.00  76.00-116.70   52
 92  \w     34.00  60.00   0.50    1.20    --   60.00  77.00 131.09   52
 93  \w     34.00  61.00   0.50    1.20    --   60.00  75.00 -15.54   54
 94  \w     64.00  89.00   0.50    1.20    --   60.00  75.00 -15.54   50
 95  \w     39.00  65.00   0.50    1.20    --   64.00  71.00  63.20   52
 96  \w     39.00  71.00   0.50    1.20    --   64.00  76.00-168.05   64
 97  \w     38.00  64.00   0.50    1.20    --   64.00  75.00 168.05   52
 98  \w     45.00  84.00   0.50    1.20    --   68.00  63.00  21.97   78
 99  \w     42.00  79.00   0.50    1.20    --   68.00  75.00 -69.92   74
100  \w     94.00 127.00   0.50    1.20    --   68.00  70.00  85.29   66
101  \w     44.00  70.00   0.50    1.20    --   68.00  70.00  85.29   52
102  \w    108.00 133.00   0.50    1.20    --   68.00  63.00  21.97   50
103  \w     46.00  78.00   0.50    1.20    --   68.00  76.00  36.92   64
104  \w     46.00  72.00   0.50    0.20    --   72.00  74.00 100.83   52
105  \w     47.00 107.00   0.50    0.20    --   72.00  73.00-101.00  120
106  \w    113.00 138.00   0.50    0.20    --   72.00  70.00  72.76   50
107  \w     47.00  72.00   0.50    0.20    --   72.00  70.00  72.76   50
108  \w     49.00  79.00   0.50    0.20    --   76.00  77.00 129.64   60
109  \w     56.00  82.00   0.50    0.20    --   80.00  69.00 164.08   52
110  \w     56.00  82.00   0.50    0.20    --   80.00  68.00-171.72   52
111  \w     99.00 138.00   0.50    0.20    --   84.00  59.00  -5.97   78
112  \w     62.00  90.00   0.50    0.20    --   84.00  59.00  -5.97   56
113  \w     61.00  87.00   0.50    0.20    --   88.00  77.00-149.61   52
114  \w     69.00  95.00   0.50    0.20    --   92.00  72.00 174.11   52
115  \w     79.00 104.00   0.50    0.20    --  100.00  61.00 -60.00   50
116  \w     86.00 150.00   0.50    0.20    --  100.00  93.00 150.00  128
117  \w     73.00 114.00   0.50    0.20    --  100.00  77.00  30.00   82
118  \w     76.00 101.00   0.50    0.20    --  100.00  69.00-120.00   50
119  \w     73.00 147.00   0.50    0.20    --  100.00  77.00  60.00  148
120  \w     73.00 105.00   0.50    0.20    --  100.00 -15.00-180.00   64
121  \w     27.00  52.00   0.50    0.20    --  100.00 -15.00-180.00   50
122  \w    130.00 156.00   0.50    0.20    --  100.00  77.00 -90.00   52
123  \w     73.00 107.00   0.50    0.20    --  100.00  77.00 -90.00   68
124  \w     74.00 122.00   0.50    0.20    --  100.00  77.00 120.00   96
125  \w    115.00 141.00   0.50    0.20    --  100.00  61.00  30.00   52
126  \w     78.00 103.00   0.50    0.20    --  100.00  61.00  30.00   50
127  \w    120.00 146.00   0.50    0.20    --  100.00  77.00 -60.00   52
128  \w    129.00 154.00   0.50    0.20    --  100.00  77.00  90.00   50
129  \w    130.00 156.00   0.50    0.20    --  100.00 111.00-120.00   52
130  \w     73.00  98.00   0.50    0.20    --  100.00  77.00 -60.00   50
131  \w     75.00 106.00   0.50    0.20    --  100.00  77.00-120.00   62
132  \w     73.00 109.00   0.50    0.20    --  100.00  77.00  90.00   72
133  \w     76.00 133.00   0.50    0.20    --  100.00  69.00-150.00  114
134  \w    132.00 157.00   0.50    0.20    --  100.00  77.00   0.00   50
135  \w     73.00 150.00   0.50    0.20    --  100.00  77.00-180.00  154
136  \w     76.00 102.00   0.50    0.20    --  100.00  69.00 -30.00   52
137  \w     83.00 137.00   0.50    0.20    --  100.00  61.00  90.00  108
138  \w    100.00 144.00   0.50    0.20    --  100.00  93.00  90.00   88
139  \w     76.00 108.00   0.50    0.20    --  100.00  77.00   0.00   64
140  \w    113.00 157.00   0.50    0.20    --  100.00  68.00  47.98   88
141  \w     76.00 101.00   0.50    0.20    --  100.00  68.00  47.98   50
142  \w     73.00 130.00   0.50    0.20    --  100.00  77.00 150.00  114
143  \w     53.00  99.00   0.50    0.20    --  100.00 -37.00-120.00   92
144  \w     76.00 103.00   0.50    0.20    --  100.00  69.00   0.00   54
145  \w    121.00 146.00   0.50    0.20    --  100.00  61.00 -60.00   50
146  \w     78.00 139.00   0.50    0.20    --  100.00  61.00 150.00  122
;
_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      0.0754398000
_diffrn_orient_matrix_UB_12      0.0723029000
_diffrn_orient_matrix_UB_13      -0.0492314000
_diffrn_orient_matrix_UB_21      0.0825591000
_diffrn_orient_matrix_UB_22      0.1602593000
_diffrn_orient_matrix_UB_23      0.0328335000
_diffrn_orient_matrix_UB_31      0.2274260000
_diffrn_orient_matrix_UB_32      -0.0739374000
_diffrn_orient_matrix_UB_33      0.0092726000
_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  0.0522
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            24149
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.422
_diffrn_reflns_theta_min         1.718
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    23.243
_exptl_absorpt_correction_T_max  0.503
_exptl_absorpt_correction_T_min  0.097
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.50a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    2.061
_exptl_crystal_description       prism
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.185
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.048
_refine_diff_density_max         1.943
_refine_diff_density_min         -1.423
_refine_diff_density_rms         0.171
_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     325
_refine_ls_number_reflns         4848
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0442
_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^)+(0.0707P)^2^+3.9964P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1211
_refine_ls_wR_factor_ref         0.1228
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4546
_reflns_number_total             4848
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc00892k2.cif
_cod_data_source_block           3
_cod_database_code               1566878
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C12 H8 Cl O3 S I '
_reflns_odcompleteness_completeness 98.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6A(H6A), C5A(H5A), C6(H6), C2(H2), C3A(H3A), C2A(H2A), C3(H3), C5(H5),
 C8A(H8A), C11A(H11A), C12(H12), C9(H9), C9A(H9A), C12A(H12A), C8(H8), C11(H11)
;
_shelx_res_checksum              95817
_shelx_hkl_checksum              75072
_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 1.834
_oxdiff_exptl_absorpt_empirical_full_min 0.539