#------------------------------------------------------------------------------
#$Date: 2023-09-06 17:02:49 +0300 (Wed, 06 Sep 2023) $
#$Revision: 286244 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/98/1569827.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1569827
loop_
_publ_author_name
'Heinen, Tobias'
'Merzenich, Sarah'
'Kwill, Angelina'
'Vasylyeva, Vera'
_publ_section_title
;
 Halogen Bonding in Sulphonamide Co-Crystals: X···π
 Preferred over X···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         'C6 F4 I2, C7 H9 N O2 S'
_chemical_formula_sum            'C13 H9 F4 I2 N O2 S'
_chemical_formula_weight         573.07
_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             2021-11-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.083(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6059(2)
_cell_length_b                   16.1462(4)
_cell_length_c                   18.2847(4)
_cell_measurement_reflns_used    10564
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.8410
_cell_measurement_theta_min      2.2340
_cell_volume                     1652.63(8)
_computing_cell_refinement       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (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    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.822
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -69.00 -10.00   0.50    7.48    --    1.50 -46.00-106.00  118
  2  ω     -8.00  42.00   0.50    7.48    --    1.50  46.00  42.00  100
  3  ω    -23.00  33.00   0.50    7.48    --    1.50 -99.00  30.00  112
  4  ω      1.00  30.00   0.50    7.48    --    1.50 -99.00-180.00   58
  5  ω    -22.00   3.00   0.50    7.48    --    1.50 -99.00 -60.00   50
  6  ω    -17.00  30.00   0.50    7.48    --    1.50 -99.00 -90.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0890745000
_diffrn_orient_matrix_UB_12      0.0211962000
_diffrn_orient_matrix_UB_13      0.0187987000
_diffrn_orient_matrix_UB_21      -0.0878696000
_diffrn_orient_matrix_UB_22      -0.0133787000
_diffrn_orient_matrix_UB_23      -0.0267664000
_diffrn_orient_matrix_UB_31      -0.0197894000
_diffrn_orient_matrix_UB_32      -0.0361036000
_diffrn_orient_matrix_UB_33      0.0209430000
_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  0.0314
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.822
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            15672
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.822
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.972
_diffrn_reflns_theta_min         2.231
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.979
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.531
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.120a (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    2.303
_exptl_crystal_description       plate
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.717
_refine_diff_density_min         -0.597
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3945
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0225
_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/[σ²(Fo²)+(0.0251P)²+1.8250P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0524
_refine_ls_wR_factor_ref         0.0545
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3519
_reflns_number_total             3945
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            2-AK_PM1_1zu1_final.cif
_cod_data_source_block           th_pm1_mo_autored
_cod_database_code               1569827
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         C13H8SNO2I2F4
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.857
_shelx_estimated_absorpt_t_min   0.587
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.07
_olex2_refinement_description
;
;
_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 1.585
_oxdiff_exptl_absorpt_empirical_full_min 0.812
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.54461(3) 0.70489(2) 1.00473(2) 0.02078(6) Uani 1 1 d . . . . .
I2 I 1.31790(3) 1.01439(2) 1.13727(2) 0.02263(6) Uani 1 1 d . . . . .
S1 S 0.18645(12) 0.55147(4) 0.89719(3) 0.01967(14) Uani 1 1 d . . . . .
F4 F 0.5938(3) 0.80067(11) 1.15695(9) 0.0269(4) Uani 1 1 d . . . . .
F1 F 0.9763(3) 0.79917(10) 0.93283(8) 0.0257(4) Uani 1 1 d . . . . .
F2 F 1.2706(3) 0.91888(11) 0.98280(9) 0.0289(4) Uani 1 1 d . . . . .
F3 F 0.8976(3) 0.91615(11) 1.20863(8) 0.0271(4) Uani 1 1 d . . . . .
O1 O 0.1591(4) 0.58008(13) 0.97117(10) 0.0267(5) Uani 1 1 d . . . . .
O2 O 0.4197(4) 0.55610(14) 0.86918(11) 0.0269(4) Uani 1 1 d . . . . .
N1 N 0.0953(5) 0.45613(15) 0.89644(12) 0.0212(5) Uani 1 1 d . . . . .
C8 C 0.7770(5) 0.79691(16) 1.04334(14) 0.0173(5) Uani 1 1 d . . . . .
C13 C 0.7610(5) 0.82861(17) 1.11336(14) 0.0189(5) Uani 1 1 d . . . . .
C12 C 0.9172(5) 0.88930(17) 1.13982(14) 0.0185(5) Uani 1 1 d . . . . .
C11 C 1.0908(5) 0.92157(17) 1.09721(14) 0.0194(5) Uani 1 1 d . . . . .
C10 C 1.1047(5) 0.88993(18) 1.02706(14) 0.0207(5) Uani 1 1 d . . . . .
C9 C 0.9533(5) 0.82816(17) 1.00109(13) 0.0186(5) Uani 1 1 d . . . . .
C2 C 0.0787(5) 0.40382(16) 0.83370(13) 0.0179(5) Uani 1 1 d . . . . .
C3 C 0.2488(5) 0.40468(17) 0.78117(15) 0.0212(5) Uani 1 1 d . . . . .
C5 C 0.0337(6) 0.29605(19) 0.71459(15) 0.0256(6) Uani 1 1 d . . . . .
C4 C 0.2225(5) 0.35143(19) 0.72139(15) 0.0236(6) Uani 1 1 d . . . . .
C1 C -0.0111(6) 0.6072(2) 0.83773(16) 0.0254(6) Uani 1 1 d . . . . .
C6 C -0.1325(6) 0.29478(19) 0.76805(16) 0.0264(6) Uani 1 1 d . . . . .
C7 C -0.1127(5) 0.34912(19) 0.82686(15) 0.0231(6) Uani 1 1 d . . . . .
H1A H -0.150(6) 0.601(2) 0.8547(18) 0.019(8) Uiso 1 1 d . . . . .
H1B H 0.048(6) 0.662(2) 0.8355(17) 0.021(8) Uiso 1 1 d . . . . .
H4 H 0.331(6) 0.355(2) 0.6898(19) 0.025(9) Uiso 1 1 d . . . . .
H1C H -0.003(7) 0.583(2) 0.790(2) 0.037(10) Uiso 1 1 d . . . . .
H3 H 0.369(6) 0.442(2) 0.7855(18) 0.026(9) Uiso 1 1 d . . . . .
H6 H -0.269(7) 0.259(2) 0.7655(19) 0.031(9) Uiso 1 1 d . . . . .
H7 H -0.220(7) 0.349(3) 0.860(2) 0.042(11) Uiso 1 1 d . . . . .
H5 H 0.024(7) 0.260(2) 0.675(2) 0.035(10) Uiso 1 1 d . . . . .
H1 H 0.012(7) 0.447(2) 0.928(2) 0.032(10) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 -1 0.0502
-1 -2 -1 0.0375
1 2 1 0.0584
0 -1 1 0.0059
0 2 1 0.0285
0 -2 -1 0.0109
1 2 -2 0.0664
-2 2 -1 0.0611
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 N1 105.20(12) . . ?
O1 S1 C1 108.68(14) . . ?
O2 S1 O1 117.59(13) . . ?
O2 S1 N1 109.88(13) . . ?
O2 S1 C1 108.01(14) . . ?
N1 S1 C1 107.02(14) . . ?
S1 N1 H1 112(3) . . ?
C2 N1 S1 125.23(19) . . ?
C2 N1 H1 118(3) . . ?
C13 C8 I1 120.5(2) . . ?
C9 C8 I1 121.73(19) . . ?
C9 C8 C13 117.7(2) . . ?
F4 C13 C8 120.4(2) . . ?
F4 C13 C12 118.7(2) . . ?
C12 C13 C8 120.9(2) . . ?
F3 C12 C13 118.3(2) . . ?
F3 C12 C11 120.2(2) . . ?
C11 C12 C13 121.4(2) . . ?
C12 C11 I2 120.74(19) . . ?
C12 C11 C10 117.3(3) . . ?
C10 C11 I2 121.9(2) . . ?
F2 C10 C11 120.2(3) . . ?
F2 C10 C9 118.4(2) . . ?
C9 C10 C11 121.4(3) . . ?
F1 C9 C8 119.9(2) . . ?
F1 C9 C10 118.9(2) . . ?
C10 C9 C8 121.2(2) . . ?
C3 C2 N1 122.2(3) . . ?
C3 C2 C7 119.9(3) . . ?
C7 C2 N1 117.8(2) . . ?
C2 C3 C4 119.3(3) . . ?
C2 C3 H3 119(2) . . ?
C4 C3 H3 122(2) . . ?
C4 C5 C6 119.0(3) . . ?
C4 C5 H5 120(2) . . ?
C6 C5 H5 121(2) . . ?
C3 C4 H4 116(2) . . ?
C5 C4 C3 121.1(3) . . ?
C5 C4 H4 123(2) . . ?
S1 C1 H1A 106(2) . . ?
S1 C1 H1B 107(2) . . ?
S1 C1 H1C 107(2) . . ?
H1A C1 H1B 116(3) . . ?
H1A C1 H1C 112(3) . . ?
H1B C1 H1C 108(3) . . ?
C5 C6 C7 120.5(3) . . ?
C5 C6 H6 123(2) . . ?
C7 C6 H6 117(2) . . ?
C2 C7 H7 119(3) . . ?
C6 C7 C2 120.1(3) . . ?
C6 C7 H7 121(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C8 2.075(3) . ?
I2 C11 2.074(3) . ?
S1 O1 1.4453(19) . ?
S1 O2 1.432(2) . ?
S1 N1 1.622(3) . ?
S1 C1 1.757(3) . ?
F4 C13 1.341(3) . ?
F1 C9 1.346(3) . ?
F2 C10 1.349(3) . ?
F3 C12 1.341(3) . ?
N1 C2 1.424(3) . ?
N1 H1 0.77(4) . ?
C8 C13 1.386(4) . ?
C8 C9 1.382(4) . ?
C13 C12 1.384(4) . ?
C12 C11 1.381(4) . ?
C11 C10 1.387(4) . ?
C10 C9 1.378(4) . ?
C2 C3 1.390(4) . ?
C2 C7 1.390(4) . ?
C3 C4 1.392(4) . ?
C3 H3 0.91(4) . ?
C5 C4 1.386(5) . ?
C5 C6 1.386(4) . ?
C5 H5 0.93(4) . ?
C4 H4 0.86(4) . ?
C1 H1A 0.86(4) . ?
C1 H1B 0.95(3) . ?
C1 H1C 0.95(4) . ?
C6 C7 1.388(4) . ?
C6 H6 0.96(4) . ?
C7 H7 0.87(4) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1A O2 0.86(4) 2.55(4) 3.375(4) 162(3) 1_455 yes
C3 H3 O2 0.91(4) 2.40(3) 3.053(4) 129(3) . yes
N1 H1 O1 0.77(4) 2.17(4) 2.934(3) 169(4) 3_567 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C8 C13 F4 -0.5(4) . . . . ?
I1 C8 C13 C12 179.2(2) . . . . ?
I1 C8 C9 F1 0.4(4) . . . . ?
I1 C8 C9 C10 179.2(2) . . . . ?
I2 C11 C10 F2 0.6(4) . . . . ?
I2 C11 C10 C9 179.9(2) . . . . ?
S1 N1 C2 C3 38.7(4) . . . . ?
S1 N1 C2 C7 -142.9(2) . . . . ?
F4 C13 C12 F3 1.5(4) . . . . ?
F4 C13 C12 C11 -178.9(3) . . . . ?
F2 C10 C9 F1 0.0(4) . . . . ?
F2 C10 C9 C8 -178.9(2) . . . . ?
F3 C12 C11 I2 -1.8(4) . . . . ?
F3 C12 C11 C10 178.7(2) . . . . ?
O1 S1 N1 C2 176.8(2) . . . . ?
O2 S1 N1 C2 -55.8(3) . . . . ?
N1 C2 C3 C4 179.5(3) . . . . ?
N1 C2 C7 C6 -177.8(3) . . . . ?
C8 C13 C12 F3 -178.3(2) . . . . ?
C8 C13 C12 C11 1.3(4) . . . . ?
C13 C8 C9 F1 179.8(2) . . . . ?
C13 C8 C9 C10 -1.3(4) . . . . ?
C13 C12 C11 I2 178.6(2) . . . . ?
C13 C12 C11 C10 -0.9(4) . . . . ?
C12 C11 C10 F2 -180.0(3) . . . . ?
C12 C11 C10 C9 -0.7(4) . . . . ?
C11 C10 C9 F1 -179.3(2) . . . . ?
C11 C10 C9 C8 1.8(4) . . . . ?
C9 C8 C13 F4 -179.9(2) . . . . ?
C9 C8 C13 C12 -0.2(4) . . . . ?
C2 C3 C4 C5 -1.9(4) . . . . ?
C3 C2 C7 C6 0.7(4) . . . . ?
C5 C6 C7 C2 -1.9(5) . . . . ?
C4 C5 C6 C7 1.1(5) . . . . ?
C1 S1 N1 C2 61.3(3) . . . . ?
C6 C5 C4 C3 0.8(4) . . . . ?
C7 C2 C3 C4 1.2(4) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0000 1.0000 -1.0000 0.0024 0.0134 -0.0570
-1.0000 -2.0000 -1.0000 0.0279 0.1414 0.0711
1.0000 2.0000 1.0000 -0.0279 -0.1414 -0.0711
0.0000 -1.0000 1.0000 -0.0024 -0.0134 0.0570
0.0000 2.0000 1.0000 0.0612 -0.0535 -0.0513
-0.0000 -2.0000 -1.0000 -0.0612 0.0535 0.0513
1.0000 2.0000 -2.0000 -0.0843 -0.0611 -0.1339
-2.0000 2.0000 -1.0000 0.2017 0.1757 -0.0536
