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_1566879
_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         'C15 H15 I O3 S'
_chemical_formula_sum            'C15 H15 I O3 S'
_chemical_formula_weight         402.23
_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
_audit_creation_date             2020-07-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-07-13 deposited with the CCDC.	2022-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                84.4790(10)
_cell_angle_beta                 82.633(2)
_cell_angle_gamma                74.902(2)
_cell_formula_units_Z            6
_cell_length_a                   10.1666(2)
_cell_length_b                   14.3384(3)
_cell_length_c                   20.5652(3)
_cell_measurement_reflns_used    33824
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.7820
_cell_measurement_theta_min      3.4240
_cell_volume                     2864.29(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.887
_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    -10.00  78.00   0.50   30.00    --   16.86  38.00  90.00  176
  2  \w    -30.00  -3.00   0.50   30.00    --  -14.99 -19.00 150.00   54
  3  \w   -100.00 -73.00   0.50   30.00    --  -14.99-178.00 150.00   54
  4  \w    -58.00  42.00   0.50   30.00    --   16.86 -38.00 -90.00  200
  5  \w      0.00  84.00   0.50   30.00    --   16.86  57.00-150.00  168
  6  \w     56.00 106.00   0.50   30.00    --   16.86 178.00-180.00  100
  7  \w    -31.00  17.00   0.50   30.00    --  -14.99 -76.00-112.00   96
  8  \w    -20.00  13.00   0.50   30.00    --  -14.99 -99.00  90.00   66
  9  \w    -55.00  79.00   0.50   30.00    --   16.86   0.00  30.00  268
 10  \w     -3.00  72.00   0.50   30.00    --   18.00-119.00  37.08  150
 11  \w      5.00  78.00   0.50   30.00    --   18.00-129.00-109.18  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0527866000
_diffrn_orient_matrix_UB_12      0.0272437000
_diffrn_orient_matrix_UB_13      -0.0186885000
_diffrn_orient_matrix_UB_21      -0.0490781000
_diffrn_orient_matrix_UB_22      -0.0177647000
_diffrn_orient_matrix_UB_23      0.0218948000
_diffrn_orient_matrix_UB_31      -0.0093589000
_diffrn_orient_matrix_UB_32      0.0397339000
_diffrn_orient_matrix_UB_33      0.0196481000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.887
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            61898
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.887
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.910
_diffrn_reflns_theta_min         3.003
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.789
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.399
_exptl_crystal_description       needle
_exptl_crystal_F_000             1188
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_platon_squeeze_details
;
TITL 14540-sns8_a.res in P-1
CELL   10.1666   14.3384   20.5652     84.48     82.63     74.90
SPGR P-1
C101 0.830 0.682 0.176 !       6.28 eA-3
Q102 0.282 0.416 0.193 !       5.26 eA-3
C103 0.594 0.214 0.003 !       4.85 eA-3
Q104 0.484 0.508 0.226 !       4.03 eA-3
C105 0.690 0.556 0.142 !       3.71 eA-3
Q106 0.422 0.567 0.191 !       3.62 eA-3
C107 0.873 0.347 0.126 !       3.44 eA-3
C108 0.671 0.707 0.030 !       3.20 eA-3
Q109 0.421 0.531 0.403 !       3.00 eA-3
C110 0.797 0.292 0.019 !       2.50 eA-3
C111 0.108 0.652 0.109 !       2.35 eA-3
C112 0.074 0.635 0.094 !       2.29 eA-3
Q113 0.329 0.711 0.416 !       2.23 eA-3
Q114 0.064 0.642 0.361 !       2.20 eA-3
C115 0.252 0.691 0.091 !       1.96 eA-3
C116 0.346 0.332 0.075 !       1.87 eA-3
Q117 0.470 0.386 0.314 !       1.85 eA-3
C118 0.142 0.382 0.077 !       1.79 eA-3
Q119 0.377 0.954 0.079 !       1.72 eA-3
Q120 0.388 0.679 0.307 !       1.69 eA-3
C121 0.544 0.727 0.011 !       1.54 eA-3
Q122 0.438 0.531 0.331 !       1.53 eA-3
Q123 0.453 0.370 0.372 !       1.53 eA-3
Q124 0.392 0.623 0.313 !       1.43 eA-3
C125 0.111 0.427 0.073 !       1.38 eA-3
C126 0.066 0.308 0.062 !       1.30 eA-3
C127 0.627 0.292 0.033 !       1.26 eA-3
Q128 0.435 0.335 0.342 !       1.16 eA-3
C129 0.191 0.507 0.136 !       1.16 eA-3
Q130 0.420 0.626 0.395 !       1.12 eA-3
Q131 0.046 0.628 0.405 !       1.12 eA-3
C132 0.544 0.529 0.025 !       1.08 eA-3
C133 0.406 0.361 0.030 !       1.05 eA-3
Q134 0.095 0.654 0.405 !       0.98 eA-3
Q135 0.017 0.653 0.389 !       0.97 eA-3
Q136 0.314 0.550 0.221 !       0.95 eA-3
C137 0.127 0.286 0.029 !       0.95 eA-3
Q138 0.076 0.474 0.412 !       0.91 eA-3
Q139 0.985 0.835 0.420 !       0.88 eA-3
C140 0.532 0.287 0.031 !       0.86 eA-3
Q141 0.312 0.096 0.074 !       0.86 eA-3
Q142 0.062 0.684 0.392 !       0.85 eA-3
Q143 0.659 0.355 0.343 !       0.85 eA-3
C144 0.466 0.439 0.027 !       0.84 eA-3
Q145 0.717 0.921 0.045 !       0.84 eA-3
C146 0.153 0.336 0.040 !       0.80 eA-3
C147 0.971 0.388 0.089 !       0.79 eA-3
Q148 0.030 0.865 0.297 !       0.79 eA-3
C149 0.123 0.551 0.115 !       0.77 eA-3
Q150 0.627 0.621 0.451 !       0.77 eA-3
Q151 0.157 0.300 0.383 !       0.75 eA-3
C152 0.473 0.520 0.031 !       0.75 eA-3
C153 0.549 0.338 0.050 !       0.75 eA-3
Q154 0.264 0.078 0.267 !       0.73 eA-3
C155 0.531 0.390 0.058 !       0.72 eA-3
C156 0.986 0.328 0.000 !       0.71 eA-3
Q157 0.985 0.930 0.286 !       0.71 eA-3
Q158 0.280 0.046 0.218 !       0.71 eA-3
Q159 0.519 0.170 0.359 !       0.71 eA-3
Q160 0.688 0.362 0.422 !       0.70 eA-3
Q161 0.108 0.404 0.345 !       0.70 eA-3
Q162 0.936 0.967 0.423 !       0.70 eA-3
Q163 0.893 0.115 0.343 !       0.70 eA-3
C164 0.282 0.342 0.013 !       0.69 eA-3
Q165 0.876 0.359 0.294 !       0.69 eA-3
C166 0.155 0.383 0.017 !       0.65 eA-3
Q167 0.437 0.573 0.405 !       0.65 eA-3
Q168 0.873 0.383 0.391 !       0.63 eA-3
Q169 0.327 0.016 0.143 !       0.63 eA-3
Q170 0.423 0.629 0.359 !       0.62 eA-3
C171 0.578 0.455 0.161 !       0.62 eA-3
Q172 0.598 0.051 0.087 !       0.62 eA-3
C173 0.294 0.697 0.045 !       0.61 eA-3
C174 0.627 0.624 0.084 !       0.61 eA-3
Q175 0.030 0.807 0.388 !       0.61 eA-3
Q176 0.593 0.008 0.310 !       0.61 eA-3
Q177 0.312 0.922 0.406 !       0.61 eA-3
Q178 0.298 0.019 0.081 !       0.60 eA-3
Q179 0.280 0.994 0.333 !       0.60 eA-3
C180 1.005 0.436 0.139 !       0.60 eA-3
Q181 0.298 0.052 0.119 !       0.60 eA-3
C182 0.279 0.601 0.123 !       0.60 eA-3
Q183 0.903 0.412 0.353 !       0.59 eA-3
Q184 0.624 0.619 0.373 !       0.59 eA-3
Q185 0.018 0.635 0.440 !       0.59 eA-3
Q186 0.530 0.170 0.312 !       0.59 eA-3
Q187 0.813 0.618 0.421 !       0.57 eA-3
Q188 0.128 0.409 0.316 !       0.57 eA-3
Q189 0.985 0.906 0.090 !       0.57 eA-3
C190 0.655 0.558 0.014 !       0.57 eA-3
Q191 0.630 0.834 0.362 !       0.57 eA-3
C192 0.205 0.342 0.030 !       0.55 eA-3
C193 0.924 0.448 0.121 !       0.55 eA-3
Q194 0.515 0.134 0.440 !       0.55 eA-3
Q195 0.985 0.835 0.457 !       0.55 eA-3
Q196 0.364 0.697 0.378 !       0.55 eA-3
C197 0.018 0.484 0.016 !       0.55 eA-3
Q198 0.637 0.060 0.061 !       0.55 eA-3
Q199 0.418 0.325 0.407 !       0.55 eA-3
;
_refine_diff_density_max         1.645
_refine_diff_density_min         -2.297
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     547
_refine_ls_number_reflns         17510
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0308
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0286P)^2^+4.2776P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0706
_refine_ls_wR_factor_ref         0.0733
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15574
_reflns_number_total             17510
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc00892k2.cif
_cod_data_source_block           1b
_cod_database_code               1566879
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C15 I1 O3 S1'
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_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. Restrained distances
 S1-O1D = S1-O1 = S1-O3D = S1-O3 = S1-O2D = S1-O2
 1.46 with sigma of 0.005
 O1-O2
 2.42 with sigma of 0.005
 O1-O3
 2.42 with sigma of 0.005
 O2-O3
 2.42 with sigma of 0.005
 O1D-O3D
 2.42 with sigma of 0.005
 O1D-O2D
 2.42 with sigma of 0.005
 O3D-O2D
 2.42 with sigma of 0.005
 S1-O3 = S1-O2D = S1-O2 = S1-O1D = S1-O1 = S1-O3D
 1.46 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
Uanis(O2) = Uanis(O2D) = Uanis(O1D) = Uanis(O1) = Uanis(O3D) = Uanis(O3)
4. Others
 Fixed Sof: O1D(0.5) O3D(0.5) O2D(0.5) O2(0.5) O1(0.5) O3(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C3B(H3B), C11B(H11B), C2B(H2B), C6(H6), C5(H5), C5B(H5B),
 C9(H9), C11A(H11A), C9A(H9A), C11(H11), C6B(H6B), C9B(H9B), C5A(H5A), C2A(H2A),
  C6A(H6A), C3A(H3A)
5.b Idealised Me refined as rotating group:
 C14B(H14D,H14E,H14F), C13A(H13G,H13H,H13I), C15B(H15D,H15E,H15F), C13B(H13D,
 H13E,H13F), C15A(H15G,H15H,H15I), C15(H15A,H15B,H15C), C14A(H14G,H14H,H14I),
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_platon_squeeze_void_probe_radius 1.20
_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 1.422
_oxdiff_exptl_absorpt_empirical_full_min 0.803