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_1569826
_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           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2022-02-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-02-17 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 102.8420(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.14950(10)
_cell_length_b                   8.96850(10)
_cell_length_c                   14.61480(10)
_cell_measurement_reflns_used    19258
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.0140
_cell_measurement_theta_min      4.0740
_cell_volume                     1680.43(3)
_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 (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 0.919
_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     51.00 102.00   0.50    0.05    --   51.23  38.00 120.00  102
  2  \w     60.00  86.00   0.50    0.05    --   51.23  40.00  56.00   52
  3  \w    106.00 156.00   0.50    0.14    --  109.96  40.00  56.00  100
  4  \w     68.00 113.00   0.50    0.14    --  109.96   0.00  90.00   90
  5  \w      4.00  38.00   0.50    0.05    --   51.23   0.00  60.00   68
  6  \w     39.00 106.00   0.50    0.14    --  109.96 -99.00 -90.00  134
  7  \w     39.00  97.00   0.50    0.14    --  109.96 -77.00 -60.00  116
  8  \w    -17.00  31.00   0.50    0.05    --   51.23 -40.00 -97.00   96
  9  \w     63.00  89.00   0.50    0.14    --  109.96 -77.00  90.00   52
 10  \w     86.00 111.00   0.50    0.14    --  109.96-125.00 150.00   50
 11  \w     40.00  65.00   0.50    0.14    --  109.96-125.00 150.00   50
 12  \w    -14.00  35.00   0.50    0.05    --   51.23 -38.00 150.00   98
 13  \w    -61.00 -18.00   0.50    0.14    --  -90.00  57.00-120.00   86
 14  \w    -70.00 -32.00   0.50    0.14    --  -90.00  57.00-180.00   76
 15  \w    -56.00 -30.00   0.50    0.14    --  -90.00  57.00 -90.00   52
 16  \w    -48.00 -23.00   0.50    0.14    --  -90.00  38.00-120.00   50
 17  \w    -48.00 -19.00   0.50    0.14    --  -90.00  38.00  30.00   58
 18  \w    -50.00 -19.00   0.50    0.14    --  -90.00  40.00  56.00   62
 19  \w    -46.00 -21.00   0.50    0.14    --  -90.00  38.00  90.00   50
 20  \w    -46.00 -19.00   0.50    0.14    --  -90.00  38.00 120.00   54
 21  \w    -31.00  11.00   0.50    0.05    --  -51.23  40.00  56.00   84
 22  \w    -48.00 -23.00   0.50    0.14    --  -90.00  38.00-180.00   50
 23  \w    -47.00 -22.00   0.50    0.14    --  -90.00  38.00-150.00   50
 24  \w    -71.00 -24.00   0.50    0.14    --  -90.00 125.00 150.00   94
 25  \w   -122.00 -34.00   0.50    0.05    --  -51.23 -77.00 120.00  176
 26  \w    -64.00 -33.00   0.50    0.05    --  -51.23 -77.00-180.00   62
 27  \w   -122.00 -94.00   0.50    0.05    --  -51.23 -77.00-180.00   56
 28  \w    -95.00 -70.00   0.50    0.14    --  -90.00 -77.00-175.21   50
 29  \w    -97.00 -71.00   0.50    0.14    --  -90.00 -77.00-180.00   52
 30  \w   -159.00-121.00   0.50    0.14    --  -90.00 -77.00-175.21   76
 31  \w   -158.00-133.00   0.50    0.14    --  -90.00 -77.00-150.00   50
 32  \w   -124.00 -71.00   0.50    0.14    --  -90.00 -77.00-150.00  106
 33  \w   -138.00 -74.00   0.50    0.14    --  -90.00 -73.00 120.37  128
 34  \w   -154.00-128.00   0.50    0.14    --  -90.00 -77.00 150.00   52
 35  \w   -145.00-119.00   0.50    0.14    --  -90.00 -73.00 165.72   52
 36  \w    -99.00 -73.00   0.50    0.14    --  -90.00 -77.00 150.00   52
 37  \w   -102.00 -76.00   0.50    0.14    --  -90.00 -66.00 146.06   52
 38  \w    -97.00 -72.00   0.50    0.14    --  -90.00 -73.00 165.72   50
 39  \w   -102.00 -77.00   0.50    0.14    --  -90.00 -60.00 177.91   50
 40  \w   -107.00 -77.00   0.50    0.14    --  -90.00 -65.00 139.12   60
 41  \w   -154.00 -80.00   0.50    0.14    --  -90.00 -53.00 142.28  148
 42  \w   -130.00 -76.00   0.50    0.14    --  -90.00 -63.00 121.88  108
 43  \w   -123.00 -78.00   0.50    0.05    --  -51.23 -40.00 -97.00   90
 44  \w    -72.00 -46.00   0.50    0.05    --  -51.23 -40.00 -97.00   52
 45  \w   -101.00 -76.00   0.50    0.14    --  -90.00 -69.00-172.82   50
 46  \w   -145.00-119.00   0.50    0.14    --  -90.00 -69.00-172.82   52
 47  \w   -161.00 -82.00   0.50    0.14    --  -90.00 -57.00-150.00  158
 48  \w   -154.00 -84.00   0.50    0.14    --  -90.00 -40.00 -97.00  140
 49  \w   -161.00-130.00   0.50    0.14    --  -90.00 -38.00 -30.00   62
 50  \w   -125.00 -92.00   0.50    0.14    --  -90.00 -38.00 -30.00   66
;
_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  0.0630
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24561
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.035
_diffrn_reflns_theta_min         5.128
_exptl_absorpt_coefficient_mu    17.934
_exptl_absorpt_correction_T_max  0.48501
_exptl_absorpt_correction_T_min  0.43273
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.98a (Rigaku Oxford Diffraction, 2021)
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    1.888
_exptl_crystal_description       sphere
_exptl_crystal_F_000             932
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_exptl_crystal_size_rad          0.128
_refine_diff_density_max         1.027
_refine_diff_density_min         -2.258
_refine_diff_density_rms         0.158
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3342
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0380
_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^)+(0.0676P)^2^+4.3212P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.0992
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3286
_reflns_number_total             3342
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            5-SM052_3-CPA_14DITFB.cif
_cod_data_source_block           sm052_3-cpa_14ditfb
_cod_database_code               1569826
_publcif_datablock.id            {8377612c-0823-47e7-87ae-7aae93bd6825}
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.141
_shelx_estimated_absorpt_t_min   0.039
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C12) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C7)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
3. Others
 Sof(I1B)=1-FVAR(1)
 Sof(I1A)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C8(H8A,H8B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
4.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_shelx_res_checksum              5094
_shelx_hkl_checksum              55823
_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
;
_publcif_funding_html
;
;