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#$Date: 2023-09-06 17:01:34 +0300 (Wed, 06 Sep 2023) $
#$Revision: 286241 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/98/1569824.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_1569824
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_sum            'C13 H9 F4 I2 N O2 S'
_chemical_formula_weight         573.07
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.96170(10)
_cell_length_b                   5.82430(10)
_cell_length_c                   32.1685(5)
_cell_measurement_temperature    100(2)
_cell_volume                     1679.06(4)
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.976
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            17831
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.814
_diffrn_reflns_theta_min         2.747
_exptl_absorpt_coefficient_mu    31.045
_exptl_crystal_density_diffrn    2.267
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_refine_diff_density_max         1.275
_refine_diff_density_min         -1.018
_refine_diff_density_rms         0.134
_refine_ls_abs_structure_details
;
 Flack x determined using 1411 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.021(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3313
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0328
_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)+(0.0614P)²+0.8826P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.0876
_reflns_Friedel_coverage         0.839
_reflns_Friedel_fraction_full    0.919
_reflns_Friedel_fraction_max     0.848
_reflns_number_gt                3221
_reflns_number_total             3313
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            1-AK-MB1-1zu1_final.cif
_cod_data_source_block           AK-MB1-1zu1_final
_cod_database_code               1569824
_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_min   0.098
_shelx_estimated_absorpt_t_max   0.456
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, 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 0.38038(5) 0.70105(6) 0.52648(2) 0.02372(15) Uani 1 1 d . . . . .
I2 I 0.68261(5) 0.29651(7) 0.71244(2) 0.02690(16) Uani 1 1 d . . . . .
S1 S 0.36881(19) 0.8155(3) 0.40951(6) 0.0183(4) Uani 1 1 d . . . . .
F3 F 0.6809(5) 0.0969(8) 0.62084(16) 0.0277(10) Uani 1 1 d . . . . .
F4 F 0.5681(6) 0.2510(9) 0.54953(16) 0.0310(11) Uani 1 1 d . . . . .
F2 F 0.4920(6) 0.7475(10) 0.69059(16) 0.0309(10) Uani 1 1 d . . . . .
F1 F 0.3812(5) 0.9046(8) 0.61942(17) 0.0304(11) Uani 1 1 d . . . . .
O1 O 0.3807(6) 0.5711(8) 0.40762(17) 0.0234(11) Uani 1 1 d . . . . .
O2 O 0.4996(5) 0.9489(9) 0.41918(17) 0.0235(10) Uani 1 1 d . . . . .
C8 C 0.4719(8) 0.5833(12) 0.5821(2) 0.0231(14) Uani 1 1 d . . . . .
C13 C 0.5486(8) 0.3772(13) 0.5840(2) 0.0217(13) Uani 1 1 d . . . . .
N1 N 0.2452(6) 0.8732(10) 0.44499(19) 0.0196(11) Uani 1 1 d D . . . .
C4 C 0.1756(9) 1.0721(16) 0.2877(3) 0.0324(18) Uani 1 1 d . . . . .
H4 H 0.132516 1.127326 0.262660 0.039 Uiso 1 1 calc R U . . .
C3 C 0.1296(9) 0.8597(17) 0.3041(3) 0.0294(16) Uani 1 1 d . . . . .
H3 H 0.055964 0.770587 0.290350 0.035 Uiso 1 1 calc R U . . .
C11 C 0.5893(8) 0.4175(12) 0.6577(2) 0.0219(14) Uani 1 1 d . . . . .
C12 C 0.6079(9) 0.2968(11) 0.6211(3) 0.0219(16) Uani 1 1 d . . . . .
C10 C 0.5122(9) 0.6233(12) 0.6564(2) 0.0228(13) Uani 1 1 d . . . . .
C9 C 0.4552(10) 0.7026(10) 0.6185(3) 0.0238(16) Uani 1 1 d . . . . .
C5 C 0.2836(12) 1.2012(12) 0.3079(3) 0.0330(19) Uani 1 1 d . . . . .
H5 H 0.315970 1.342114 0.296096 0.040 Uiso 1 1 calc R U . . .
C2 C 0.1941(9) 0.7822(12) 0.3410(3) 0.0236(15) Uani 1 1 d . . . . .
H2 H 0.165712 0.637604 0.352177 0.028 Uiso 1 1 calc R U . . .
C6 C 0.3456(9) 1.1263(13) 0.3456(2) 0.0265(14) Uani 1 1 d . . . . .
H6 H 0.417239 1.216747 0.359990 0.032 Uiso 1 1 calc R U . . .
C7 C 0.2040(9) 1.1173(12) 0.4512(3) 0.0252(15) Uani 1 1 d . . . . .
H7A H 0.293990 1.207133 0.457095 0.038 Uiso 1 1 calc R U . . .
H7B H 0.134702 1.129780 0.474690 0.038 Uiso 1 1 calc R U . . .
H7C H 0.156000 1.176217 0.426018 0.038 Uiso 1 1 calc R U . . .
C1 C 0.2987(8) 0.9142(11) 0.3614(2) 0.0210(13) Uani 1 1 d . . . . .
H1 H 0.164(9) 0.786(18) 0.442(5) 0.05(4) Uiso 1 1 d D . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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 O2 119.1(3) . . ?
O1 S1 N1 106.7(3) . . ?
O2 S1 N1 106.9(3) . . ?
O1 S1 C1 108.3(3) . . ?
O2 S1 C1 107.6(3) . . ?
N1 S1 C1 107.8(3) . . ?
C9 C8 C13 117.1(7) . . ?
C9 C8 I1 121.6(6) . . ?
C13 C8 I1 121.2(6) . . ?
F4 C13 C8 120.1(7) . . ?
F4 C13 C12 118.4(7) . . ?
C8 C13 C12 121.4(7) . . ?
C7 N1 S1 117.6(5) . . ?
C7 N1 H1 111(9) . . ?
S1 N1 H1 111(10) . . ?
C5 C4 C3 120.3(8) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C2 C3 C4 118.9(8) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C12 C11 C10 118.3(7) . . ?
C12 C11 I2 120.2(5) . . ?
C10 C11 I2 121.5(5) . . ?
F3 C12 C11 120.5(8) . . ?
F3 C12 C13 118.5(7) . . ?
C11 C12 C13 121.0(7) . . ?
F2 C10 C11 120.9(7) . . ?
F2 C10 C9 119.4(7) . . ?
C11 C10 C9 119.7(7) . . ?
F1 C9 C8 120.9(8) . . ?
F1 C9 C10 116.6(7) . . ?
C8 C9 C10 122.4(7) . . ?
C4 C5 C6 120.8(8) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C2 C3 120.4(7) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C1 C6 C5 117.9(8) . . ?
C1 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 C1 C6 121.6(7) . . ?
C2 C1 S1 118.5(6) . . ?
C6 C1 S1 119.9(6) . . ?
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 2.085(8) . ?
I2 C11 2.072(7) . ?
S1 O1 1.429(5) . ?
S1 O2 1.440(5) . ?
S1 N1 1.626(6) . ?
S1 C1 1.766(8) . ?
F3 C12 1.336(9) . ?
F4 C13 1.343(9) . ?
F2 C10 1.329(9) . ?
F1 C9 1.351(9) . ?
C8 C9 1.370(11) . ?
C8 C13 1.385(10) . ?
C13 C12 1.387(12) . ?
N1 C7 1.482(8) . ?
N1 H1 0.89(3) . ?
C4 C5 1.387(14) . ?
C4 C3 1.407(13) . ?
C4 H4 0.9500 . ?
C3 C2 1.395(12) . ?
C3 H3 0.9500 . ?
C11 C12 1.382(11) . ?
C11 C10 1.384(10) . ?
C10 C9 1.399(12) . ?
C5 C6 1.404(12) . ?
C5 H5 0.9500 . ?
C2 C1 1.378(11) . ?
C2 H2 0.9500 . ?
C6 C1 1.400(10) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
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
C6 H6 O1 0.95 2.59 3.284(9) 130.1 1_565 yes
C7 H7B F4 0.98 2.58 3.474(9) 152.5 3_465 yes
C7 H7C O2 0.98 2.60 3.287(9) 126.9 3_475 yes
N1 H1 S1 0.89(3) 2.91(7) 3.726(6) 153(12) 3_465 yes
N1 H1 O2 0.89(3) 2.14(5) 3.009(7) 164(14) 3_465 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
C9 C8 C13 F4 179.6(7) . . . . ?
I1 C8 C13 F4 1.4(10) . . . . ?
C9 C8 C13 C12 -0.9(10) . . . . ?
I1 C8 C13 C12 -179.1(6) . . . . ?
O1 S1 N1 C7 -176.0(5) . . . . ?
O2 S1 N1 C7 55.6(6) . . . . ?
C1 S1 N1 C7 -59.9(6) . . . . ?
C5 C4 C3 C2 0.2(12) . . . . ?
C10 C11 C12 F3 -179.7(6) . . . . ?
I2 C11 C12 F3 2.6(10) . . . . ?
C10 C11 C12 C13 -1.1(11) . . . . ?
I2 C11 C12 C13 -178.8(6) . . . . ?
F4 C13 C12 F3 -0.4(11) . . . . ?
C8 C13 C12 F3 -179.9(7) . . . . ?
F4 C13 C12 C11 -179.0(7) . . . . ?
C8 C13 C12 C11 1.5(11) . . . . ?
C12 C11 C10 F2 -179.5(7) . . . . ?
I2 C11 C10 F2 -1.8(10) . . . . ?
C12 C11 C10 C9 0.2(10) . . . . ?
I2 C11 C10 C9 177.9(6) . . . . ?
C13 C8 C9 F1 -179.7(7) . . . . ?
I1 C8 C9 F1 -1.5(11) . . . . ?
C13 C8 C9 C10 0.0(12) . . . . ?
I1 C8 C9 C10 178.2(6) . . . . ?
F2 C10 C9 F1 -0.2(12) . . . . ?
C11 C10 C9 F1 -180.0(7) . . . . ?
F2 C10 C9 C8 -180.0(7) . . . . ?
C11 C10 C9 C8 0.3(12) . . . . ?
C3 C4 C5 C6 -1.9(13) . . . . ?
C4 C3 C2 C1 1.4(12) . . . . ?
C4 C5 C6 C1 2.0(13) . . . . ?
C3 C2 C1 C6 -1.2(12) . . . . ?
C3 C2 C1 S1 176.4(6) . . . . ?
C5 C6 C1 C2 -0.5(11) . . . . ?
C5 C6 C1 S1 -178.1(7) . . . . ?
O1 S1 C1 C2 36.0(7) . . . . ?
O2 S1 C1 C2 166.0(6) . . . . ?
N1 S1 C1 C2 -79.0(6) . . . . ?
O1 S1 C1 C6 -146.3(6) . . . . ?
O2 S1 C1 C6 -16.3(7) . . . . ?
N1 S1 C1 C6 98.7(6) . . . . ?
