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#$Date: 2023-09-06 17:01:08 +0300 (Wed, 06 Sep 2023) $
#$Revision: 286240 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/98/1569823.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_1569823
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         '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  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -13.00  70.00   0.50   13.49    --   -2.10  62.00-131.00  166
  2  ω    -69.00 -29.00   0.50   13.49    --   -2.10 -62.00  90.00   80
  3  ω     26.00  52.00   0.50   13.49    --    4.60  62.00-131.00   52
  4  ω    -29.00  18.00   0.50   13.49    --    4.60 -62.00  90.00   94
  5  ω    -58.00  46.00   0.50   13.49    --   -2.10   0.00 120.00  208
  6  ω    -23.00  26.00   0.50   13.49    --   -2.10 -99.00 150.00   98
  7  ω     -8.00  61.00   0.50   13.49    --   -2.10  12.00 171.02  138
  8  ω    -23.00  27.00   0.50   13.49    --   -2.10 -99.00-120.00  100
  9  ω    -66.00  53.00   0.50   13.49    --    4.60   0.00 -90.00  238
 10  ω    -12.00  34.00   0.50   13.49    --    4.60 -99.00 -60.00   92
 11  ω    -69.00  -4.00   0.50   13.49    --    4.60 -19.00-120.00  130
 12  ω    -23.00  29.00   0.50   13.49    --    4.60 -99.00-180.00  104
 13  ω    -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       'ω 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/[σ²(Fo²)+(0.0230P)²+1.9094P] where P=(Fo²+2Fc²)/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 > 2σ(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_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   0.153
_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)
;
_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
;
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
S1 S 0.29430(4) 0.46908(5) 0.59040(3) 0.01679(11) Uani 1 1 d . . . . .
Cl2 Cl 0.78609(4) 0.50511(8) 0.69667(4) 0.03440(16) Uani 1 1 d . . . . .
C C 0.43347(16) 0.4798(2) 0.62318(14) 0.0175(4) Uani 1 1 d . . . . .
O2 O 0.28767(12) 0.62510(16) 0.77166(10) 0.0216(3) Uani 1 1 d . . . . .
C2 C 0.48497(18) 0.5970(3) 0.67941(16) 0.0229(4) Uani 1 1 d . . . . .
C3 C 0.48962(17) 0.3708(2) 0.58937(16) 0.0222(4) Uani 1 1 d . . . . .
N4 N 0.25516(14) 0.4080(2) 0.84009(13) 0.0198(4) Uani 1 1 d . . . . .
N5 N 0.26083(14) 0.4083(2) 0.68453(13) 0.0184(4) Uani 1 1 d . . . . .
C1 C 0.59897(18) 0.3792(3) 0.61236(16) 0.0250(5) Uani 1 1 d . . . . .
C7 C 0.26899(15) 0.4899(2) 0.76849(14) 0.0175(4) Uani 1 1 d . . . . .
C8 C 0.64970(17) 0.4955(3) 0.66878(15) 0.0244(5) Uani 1 1 d . . . . .
C9 C 0.26024(17) 0.4692(3) 0.93439(15) 0.0210(4) Uani 1 1 d . . . . .
C12 C 0.59440(18) 0.6045(3) 0.70262(16) 0.0265(5) Uani 1 1 d . . . . .
C4 C 0.1597(2) 0.5289(3) 1.05400(17) 0.0302(5) Uani 1 1 d . . . . .
C5 C 0.15174(18) 0.4793(3) 0.95199(16) 0.0243(5) Uani 1 1 d . . . . .
O3 O 0.26309(11) 0.35124(17) 0.52239(10) 0.0213(3) Uani 1 1 d . . . . .
O4 O 0.25388(11) 0.61686(16) 0.56787(10) 0.0209(3) Uani 1 1 d . . . . .
Br1 Br 0.5059(3) 0.2447(5) 0.8351(4) 0.0417(6) Uani 0.526(18) 1 d . . P A 1
H9A H 0.307(2) 0.407(3) 0.9813(18) 0.022(6) Uiso 1 1 d . . . . .
H3 H 0.4554(19) 0.296(3) 0.5515(17) 0.020(6) Uiso 1 1 d . . . . .
H9B H 0.2911(19) 0.565(3) 0.9384(17) 0.019(6) Uiso 1 1 d . . . . .
H2 H 0.445(2) 0.667(3) 0.7012(18) 0.024(6) Uiso 1 1 d . . . . .
H5A H 0.109(2) 0.548(3) 0.9072(19) 0.028(7) Uiso 1 1 d . . . . .
H1 H 0.639(2) 0.308(3) 0.5899(19) 0.031(7) Uiso 1 1 d . . . . .
H12 H 0.631(2) 0.681(3) 0.7401(18) 0.027(7) Uiso 1 1 d . . . . .
H4A H 0.206(2) 0.458(3) 1.100(2) 0.038(8) Uiso 1 1 d . . . . .
H5B H 0.116(2) 0.383(3) 0.9397(19) 0.033(7) Uiso 1 1 d . . . . .
H4B H 0.091(3) 0.532(3) 1.065(2) 0.046(8) Uiso 1 1 d . . . . .
H5 H 0.253(2) 0.322(4) 0.686(2) 0.035(8) Uiso 1 1 d . . . . .
H4 H 0.245(2) 0.321(3) 0.8320(19) 0.029(7) Uiso 1 1 d . . . . .
H4C H 0.189(2) 0.622(4) 1.068(2) 0.038(8) Uiso 1 1 d . . . . .
C6A C 0.49592(18) -0.0394(3) 0.90817(17) 0.0358(6) Uani 1 1 d D U . . .
Br1A Br 0.5138(3) 0.2768(9) 0.8560(4) 0.0550(8) Uani 0.474(18) 1 d . U P A 2
C10A C 0.50345(18) 0.1095(3) 0.93310(19) 0.0370(6) Uani 1 1 d D U . . .
C11A C 0.50728(18) 0.1477(3) 1.02633(19) 0.0371(6) Uani 1 1 d D U . . .
F3A F 0.49033(12) -0.0804(2) 0.81791(11) 0.0522(5) Uani 1 1 d D U . . .
F4A F 0.51403(13) 0.2908(2) 1.05410(15) 0.0561(5) Uani 1 1 d D U . . .
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
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
-2 -3 5 0.3822
-2 5 -1 0.3698
5 0 3 0.8198
3 0 -5 0.6200
2 -5 -3 0.4797
1 -1 -5 0.5970
0 0 1 0.8059
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
N5 S1 C 106.52(9) . . ?
O3 S1 C 108.13(9) . . ?
O3 S1 N5 103.93(9) . . ?
O3 S1 O4 120.30(9) . . ?
O4 S1 C 107.83(9) . . ?
O4 S1 N5 109.36(9) . . ?
C2 C S1 120.39(16) . . ?
C2 C C3 121.09(19) . . ?
C3 C S1 118.49(16) . . ?
C C2 H2 118.9(16) . . ?
C12 C2 C 119.3(2) . . ?
C12 C2 H2 121.8(16) . . ?
C C3 H3 120.6(16) . . ?
C1 C3 C 119.4(2) . . ?
C1 C3 H3 120.0(16) . . ?
C7 N4 C9 123.23(19) . . ?
C7 N4 H4 119(2) . . ?
C9 N4 H4 118(2) . . ?
S1 N5 H5 114(2) . . ?
C7 N5 S1 125.37(15) . . ?
C7 N5 H5 119(2) . . ?
C3 C1 H1 121.5(17) . . ?
C8 C1 C3 119.2(2) . . ?
C8 C1 H1 119.3(17) . . ?
O2 C7 N4 125.57(19) . . ?
O2 C7 N5 120.80(19) . . ?
N4 C7 N5 113.63(18) . . ?
C1 C8 Cl2 118.75(18) . . ?
C1 C8 C12 121.7(2) . . ?
C12 C8 Cl2 119.50(18) . . ?
N4 C9 C5 111.85(18) . . ?
N4 C9 H9A 108.0(15) . . ?
N4 C9 H9B 108.0(14) . . ?
C5 C9 H9A 111.2(15) . . ?
C5 C9 H9B 110.0(15) . . ?
H9A C9 H9B 108(2) . . ?
C2 C12 H12 121.2(16) . . ?
C8 C12 C2 119.3(2) . . ?
C8 C12 H12 119.5(16) . . ?
C5 C4 H4A 109.5(16) . . ?
C5 C4 H4B 110.4(18) . . ?
C5 C4 H4C 113.6(18) . . ?
H4A C4 H4B 110(2) . . ?
H4A C4 H4C 106(2) . . ?
H4B C4 H4C 107(3) . . ?
C9 C5 C4 111.0(2) . . ?
C9 C5 H5A 109.4(16) . . ?
C9 C5 H5B 110.6(16) . . ?
C4 C5 H5A 110.5(16) . . ?
C4 C5 H5B 109.7(16) . . ?
H5A C5 H5B 106(2) . . ?
C11A C6A C10A 121.1(2) 3_657 . ?
F3A C6A C10A 120.1(3) . . ?
F3A C6A C11A 118.8(3) . 3_657 ?
C6A C10A Br1 116.1(3) . . ?
C6A C10A Br1A 128.3(3) . . ?
C6A C10A C11A 118.5(3) . . ?
C11A C10A Br1 125.4(3) . . ?
C11A C10A Br1A 113.2(4) . . ?
C6A C11A C10A 120.4(3) 3_657 . ?
F4A C11A C6A 118.7(2) . 3_657 ?
F4A C11A C10A 120.9(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
S1 C 1.767(2) . ?
S1 N5 1.6398(18) . ?
S1 O3 1.4294(15) . ?
S1 O4 1.4315(15) . ?
Cl2 C8 1.733(2) . ?
C C2 1.390(3) . ?
C C3 1.392(3) . ?
O2 C7 1.234(2) . ?
C2 C12 1.390(3) . ?
C2 H2 0.92(3) . ?
C3 C1 1.389(3) . ?
C3 H3 0.91(3) . ?
N4 C7 1.326(3) . ?
N4 C9 1.462(3) . ?
N4 H4 0.80(3) . ?
N5 C7 1.403(3) . ?
N5 H5 0.78(3) . ?
C1 C8 1.382(3) . ?
C1 H1 0.95(3) . ?
C8 C12 1.385(3) . ?
C9 C5 1.520(3) . ?
C9 H9A 0.96(3) . ?
C9 H9B 0.95(3) . ?
C12 H12 0.93(3) . ?
C4 C5 1.525(3) . ?
C4 H4A 1.00(3) . ?
C4 H4B 0.97(3) . ?
C4 H4C 0.92(3) . ?
C5 H5A 0.96(3) . ?
C5 H5B 0.97(3) . ?
Br1 C10A 1.877(4) . ?
C6A C10A 1.378(4) . ?
C6A C11A 1.369(4) 3_657 ?
C6A F3A 1.346(3) . ?
Br1A C10A 1.899(5) . ?
C10A C11A 1.386(4) . ?
C11A F4A 1.340(3) . ?
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
S1 C C2 C12 -178.73(17) . . . . ?
S1 C C3 C1 178.42(16) . . . . ?
S1 N5 C7 O2 11.4(3) . . . . ?
S1 N5 C7 N4 -168.44(15) . . . . ?
Cl2 C8 C12 C2 179.47(17) . . . . ?
C S1 N5 C7 70.64(19) . . . . ?
C C2 C12 C8 0.4(3) . . . . ?
C C3 C1 C8 0.3(3) . . . . ?
C2 C C3 C1 0.1(3) . . . . ?
C3 C C2 C12 -0.4(3) . . . . ?
C3 C1 C8 Cl2 -179.82(17) . . . . ?
C3 C1 C8 C12 -0.4(3) . . . . ?
N4 C9 C5 C4 174.44(19) . . . . ?
N5 S1 C C2 -76.98(19) . . . . ?
N5 S1 C C3 104.69(17) . . . . ?
C1 C8 C12 C2 0.0(3) . . . . ?
C7 N4 C9 C5 107.2(2) . . . . ?
C9 N4 C7 O2 0.1(3) . . . . ?
C9 N4 C7 N5 179.95(18) . . . . ?
O3 S1 C C2 171.83(17) . . . . ?
O3 S1 C C3 -6.49(19) . . . . ?
O3 S1 N5 C7 -175.28(17) . . . . ?
O4 S1 C C2 40.31(19) . . . . ?
O4 S1 C C3 -138.02(16) . . . . ?
O4 S1 N5 C7 -45.64(19) . . . . ?
Br1 C10A C11A C6A 179.4(2) . . . 3_657 ?
Br1 C10A C11A F4A -0.5(4) . . . . ?
C6A C10A C11A C6A 0.3(4) . . . 3_657 ?
C6A C10A C11A F4A -179.6(2) . . . . ?
Br1A C10A C11A C6A -178.0(2) . . . 3_657 ?
Br1A C10A C11A F4A 2.1(3) . . . . ?
C11A C6A C10A Br1 -179.5(2) 3_657 . . . ?
C11A C6A C10A Br1A 177.7(2) 3_657 . . . ?
C11A C6A C10A C11A -0.3(4) 3_657 . . . ?
F3A C6A C10A Br1 -0.3(3) . . . . ?
F3A C6A C10A Br1A -3.1(4) . . . . ?
F3A C6A C10A C11A 178.9(2) . . . . ?
