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_1569823
_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         'C10 H13 Cl N2 O3 S, Br C3 F2'
_chemical_formula_sum            'C13 H13 Br Cl F2 N2 O3 S'
_chemical_formula_weight         430.67
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-02-07
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_cell_angle_alpha                90
_cell_angle_beta                 105.584(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1627(2)
_cell_length_b                   8.95812(18)
_cell_length_c                   14.5445(3)
_cell_measurement_reflns_used    19836
_cell_measurement_temperature    100.00(11)
_cell_measurement_theta_max      30.6740
_cell_measurement_theta_min      2.5240
_cell_volume                     1651.94(6)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -13.00  70.00   0.50   13.49    --   -2.10  62.00-131.00  166
  2  \w    -69.00 -29.00   0.50   13.49    --   -2.10 -62.00  90.00   80
  3  \w     26.00  52.00   0.50   13.49    --    4.60  62.00-131.00   52
  4  \w    -29.00  18.00   0.50   13.49    --    4.60 -62.00  90.00   94
  5  \w    -58.00  46.00   0.50   13.49    --   -2.10   0.00 120.00  208
  6  \w    -23.00  26.00   0.50   13.49    --   -2.10 -99.00 150.00   98
  7  \w     -8.00  61.00   0.50   13.49    --   -2.10  12.00 171.02  138
  8  \w    -23.00  27.00   0.50   13.49    --   -2.10 -99.00-120.00  100
  9  \w    -66.00  53.00   0.50   13.49    --    4.60   0.00 -90.00  238
 10  \w    -12.00  34.00   0.50   13.49    --    4.60 -99.00 -60.00   92
 11  \w    -69.00  -4.00   0.50   13.49    --    4.60 -19.00-120.00  130
 12  \w    -23.00  29.00   0.50   13.49    --    4.60 -99.00-180.00  104
 13  \w    -53.00  15.00   0.50   13.49    --    6.00 -36.00  36.84  136
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            44260
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.439
_exptl_absorpt_coefficient_mu    2.811
_exptl_absorpt_correction_T_max  0.12734
_exptl_absorpt_correction_T_min  0.10546
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.92a (Rigaku Oxford Diffraction, 2020)
Spherical absorption correction
using equivalent radius and absorption coefficient.
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    1.732
_exptl_crystal_description       block
_exptl_crystal_F_000             860
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_size_rad          0.736
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         3378
_refine_ls_number_restraints     33
_refine_ls_restrained_S_all      1.168
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0340
_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^)+(0.0230P)^2^+1.9094P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0711
_refine_ls_wR_factor_ref         0.0721
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3247
_reflns_number_total             3378
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            6-SM014-CPA_14DBTFB.cif
_cod_data_source_block           th_sm14_autored
_cod_database_code               1569823
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.153
_shelx_estimated_absorpt_t_min   0.036
_olex2_refinement_description
;
1. Restrained distances
 C11A-C6A
 2.4 with sigma of 0.04
 C11A-C10A \\sim C10A-C6A
 with sigma of 0.02
 C11A-F4A \\sim C6A-F3A
 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
F4A \\sim C11A \\sim C10A \\sim Br1A \\sim C6A \\sim F3A: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02 within 2A
Br1: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
3. Others
 Sof(Br1A)=1-FVAR(1)
 Sof(Br1)=FVAR(1)
;
_shelx_res_checksum              52606
_shelx_hkl_checksum              40613
_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
;