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_1569822
_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, C10 H13 Cl N2 O3 S'
_chemical_formula_sum            'C13 H13 Cl F2 I N2 O3 S'
_chemical_formula_weight         477.66
_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   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2022-02-07
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.9650(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.9967(2)
_cell_length_b                   8.90250(10)
_cell_length_c                   22.2511(3)
_cell_measurement_reflns_used    33693
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      30.4170
_cell_measurement_theta_min      2.4130
_cell_volume                     3348.65(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_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    -68.00   9.00   0.50    4.59    --    1.79 -38.00  60.00  154
  2  \w    -44.00  10.00   0.50    4.59    --    1.79 -38.00   0.00  108
  3  \w    -23.00  33.00   0.50    4.59    --    1.96 -99.00 -30.00  112
  4  \w    -21.00  33.00   0.50    4.59    --    1.96 -99.00-150.00  108
  5  \w    -49.00  46.00   0.50    4.59    --    1.96   0.00-180.00  190
  6  \w    -50.00  -8.00   0.50    4.59    --    1.96   0.00  30.00   84
  7  \w    -23.00  32.00   0.50    4.59    --    1.96 -99.00 -90.00  110
  8  \w      2.00  41.00   0.50    4.59    --    1.96   0.00  30.00   78
  9  \w    -19.00  33.00   0.50    4.59    --    1.96 -99.00 120.00  104
 10  \w    -69.00  10.00   0.50    4.59    --    1.96 -38.00 150.00  158
 11  \w    -70.00  12.00   0.50    4.59    --    1.96  -4.00 -63.24  164
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0277229000
_diffrn_orient_matrix_UB_12      -0.0307322000
_diffrn_orient_matrix_UB_13      0.0227309000
_diffrn_orient_matrix_UB_21      -0.0111119000
_diffrn_orient_matrix_UB_22      0.0544535000
_diffrn_orient_matrix_UB_23      0.0208084000
_diffrn_orient_matrix_UB_31      -0.0294724000
_diffrn_orient_matrix_UB_32      -0.0493914000
_diffrn_orient_matrix_UB_33      0.0087933000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0112
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.898
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            41319
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.132
_diffrn_reflns_theta_min         2.410
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.231
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.274
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.98a (Rigaku Oxford Diffraction, 2021)
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    1.895
_exptl_crystal_description       block
_exptl_crystal_F_000             1864
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.326
_exptl_crystal_size_min          0.206
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.564
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         4452
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0186
_refine_ls_R_factor_gt           0.0177
_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^)+(0.0180P)^2^+5.5679P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0436
_refine_ls_wR_factor_ref         0.0439
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4289
_reflns_number_total             4452
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            7-SM068_Mo-CPA_12DITFB.cif
_cod_data_source_block           th_sm068_mo_autored
_cod_database_code               1569822
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C13 H13 Cl F2 I N2 O3 S'
_shelx_estimated_absorpt_t_max   0.656
_shelx_estimated_absorpt_t_min   0.396
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.07
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All H(H) groups
;
_shelx_res_checksum              54682
_shelx_hkl_checksum              4427
_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 1.500
_oxdiff_exptl_absorpt_empirical_full_min 0.603