Halogen Bonding in Sulphonamide Co-Crystals: X···π Preferred over X···O/N?
Heinen, Tobias; Merzenich, Sarah; Kwill, Angelina; Vasylyeva, Vera; Molecules (Basel, Switzerland) 28 (2023) 5910–; doi:10.3390/molecules28155910

data_1569825
_publ_section_title
;
 Halogen Bonding in Sulphonamide Co-Crystals: X&#xb7;&#xb7;&#xb7;&#x3c0;
 Preferred over X&#xb7;&#xb7;&#xb7;O/N?
;
_journal_issue                   15
_journal_name_full               'Molecules (Basel, Switzerland)'
_journal_page_first              5910
_journal_paper_doi               10.3390/molecules28155910
_journal_volume                  28
_journal_year                    2023
_chemical_formula_moiety         'C3 F2 I, C7 H9 N O2 S'
_chemical_formula_sum            'C10 H9 F2 I N O2 S'
_chemical_formula_weight         372.14
_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   difmap
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-02-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.479(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4061(3)
_cell_length_b                   5.74650(10)
_cell_length_c                   18.4124(4)
_cell_measurement_reflns_used    5970
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.0710
_cell_measurement_theta_min      4.7750
_cell_volume                     1206.80(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.92a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.92a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.92a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.898
_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    128.00 155.00   0.50    1.27    --  109.96  36.00 -36.00   54
  2  \w    113.00 174.00   0.50    1.27    --  109.96  19.00 -90.00  122
  3  \w     53.00  85.00   0.50    0.32    --   51.23  36.00 -36.00   64
  4  \w    -19.00  13.00   0.50    0.32    --   51.23 -19.00  60.00   64
  5  \w    -14.00  13.00   0.50    0.32    --   51.23 -19.00-180.00   54
  6  \w    -16.00  10.00   0.50    0.32    --   51.23 -19.00  30.00   52
  7  \w    -16.00   9.00   0.50    0.32    --   51.23 -36.00 166.00   50
  8  \w   -119.00 -49.00   0.50    0.32    --  -51.23 -36.00 166.00  140
  9  \w   -161.00 -99.00   0.50    1.27    --  -90.00 -36.00 166.00  124
 10  \w   -103.00 -75.00   0.50    0.32    --  -51.23-125.00 120.00   56
 11  \w    -52.00 -25.00   0.50    1.27    --  -90.00 125.00  30.00   54
 12  \w    -82.00 -55.00   0.50    1.27    --  -90.00 125.00  30.00   54
 13  \w    -67.00 -28.00   0.50    1.27    --  -90.00  57.00 120.00   78
 14  \w    -70.00 -26.00   0.50    1.27    --  -90.00  57.00 150.00   88
 15  \w    -59.00 -34.00   0.50    1.27    --  -90.00  57.00  90.00   50
 16  \w    -66.00 -18.00   0.50    1.27    --  -90.00  57.00  60.00   96
 17  \w    -69.00 -19.00   0.50    1.27    --  -90.00  57.00  30.00  100
 18  \w    -60.00 -24.00   0.50    1.27    --  -90.00  57.00 -30.00   72
 19  \w    -65.00 -40.00   0.50    1.27    --  -90.00  57.00 -60.00   50
 20  \w    -67.00 -37.00   0.50    1.27    --  -90.00  57.00 -90.00   60
 21  \w    -66.00 -37.00   0.50    1.27    --  -90.00  57.00-120.00   58
 22  \w    -48.00 -20.00   0.50    1.27    --  -90.00  38.00-120.00   56
 23  \w    -44.00  11.00   0.50    0.32    --  -51.23  36.00 -36.00  110
 24  \w    -46.00 -21.00   0.50    1.27    --  -90.00  36.00 -36.00   50
 25  \w    -47.00 -20.00   0.50    1.27    --  -90.00  38.00  30.00   54
 26  \w    -48.00 -22.00   0.50    1.27    --  -90.00  38.00  60.00   52
 27  \w   -131.00 -89.00   0.50    1.27    --  -90.00   0.00  30.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.898
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8322
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.849
_diffrn_reflns_theta_min         3.876
_exptl_absorpt_coefficient_mu    22.656
_exptl_absorpt_correction_T_max  0.517
_exptl_absorpt_correction_T_min  0.222
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.92a (Rigaku Oxford Diffraction, 2020)
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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.048
_exptl_crystal_description       block
_exptl_crystal_F_000             716
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.632
_refine_diff_density_min         -0.730
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2285
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0271
_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^)+(0.0480P)^2^+0.4645P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0749
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2119
_reflns_number_total             2285
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            3-AK-PM1_2zu1_final.cif
_cod_data_source_block           ak-pm1_final
_cod_database_code               1569825
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.397
_shelx_estimated_absorpt_t_min   0.172
_olex2_refinement_description
;
;
_shelx_res_checksum              10460
_shelx_hkl_checksum              24589
_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
;