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_1569821
_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, C12 H11 N O2 S'
_chemical_formula_sum            'C15 H11 F2 I N O2 S'
_chemical_formula_weight         434.21
_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     dual
_audit_creation_date             2021-11-29
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.244(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6190(2)
_cell_length_b                   6.03240(10)
_cell_length_c                   23.9571(6)
_cell_measurement_reflns_used    7500
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.2290
_cell_measurement_theta_min      2.1840
_cell_volume                     1528.22(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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.811
_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    -23.00  28.00   0.50    0.84    --    1.96 -99.00  60.00  102
  2  \w    -19.00  12.00   0.50    0.84    --    1.96 -99.00 150.00   62
  3  \w    -69.00 -28.00   0.50    0.84    --    1.72 -19.00 120.00   82
  4  \w    -12.00  74.00   0.50    0.84    --    1.96  77.00-150.00  172
;
_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      0.0605108000
_diffrn_orient_matrix_UB_12      0.0506997000
_diffrn_orient_matrix_UB_13      0.0016001000
_diffrn_orient_matrix_UB_21      -0.0285077000
_diffrn_orient_matrix_UB_22      0.1026608000
_diffrn_orient_matrix_UB_23      -0.0081602000
_diffrn_orient_matrix_UB_31      -0.0051781000
_diffrn_orient_matrix_UB_32      0.0264691000
_diffrn_orient_matrix_UB_33      0.0285547000
_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  0.0273
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.811
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            11111
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.811
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.114
_diffrn_reflns_theta_min         2.034
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.259
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.517
_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    1.887
_exptl_crystal_description       block
_exptl_crystal_F_000             844
_exptl_crystal_size_max          0.258
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.097
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3659
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0222
_refine_ls_R_factor_gt           0.0202
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0143P)^2^+0.8918P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0450
_refine_ls_wR_factor_ref         0.0458
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3418
_reflns_number_total             3659
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            4-AK-B1_2zu1_final.cif
_cod_data_source_block           th_ak_b1_mo_autored
_cod_database_code               1569821
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         C15H11N1O2S1F2I1
_chemical_oxdiff_usercomment     block
_shelx_estimated_absorpt_t_max   0.811
_shelx_estimated_absorpt_t_min   0.593
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.07
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All H(H) groups
;
_shelx_res_checksum              57728
_shelx_hkl_checksum              93319
_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 1.382
_oxdiff_exptl_absorpt_empirical_full_min 0.857