#------------------------------------------------------------------------------
#$Date: 2022-07-23 02:30:02 +0300 (Sat, 23 Jul 2022) $
#$Revision: 276813 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/51/7245161.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_7245161
loop_
_publ_author_name
'Tan, Sang Loon'
'Lo, Kong Mun'
'Tan, Yee Seng'
'Tiekink, Edward R. T.'
_publ_section_title
;
 Structural systematics in the isomorphous binary co-crystal solvates
 comprising 2,2'-dithiodibenzoic acid, 4-halobenzoic acid and
 dimethylformamide (1:1:1), for halide = chloride, bromide and iodide
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00094F
_journal_year                    2022
_chemical_formula_moiety         'C14 H10 O4 S2, C7 H5 I O2, C3 H7 N O'
_chemical_formula_sum            'C24 H22 I N O7 S2'
_chemical_formula_weight         627.44
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-01-15 deposited with the CCDC.	2022-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                93.9320(10)
_cell_angle_beta                 98.3930(10)
_cell_angle_gamma                97.7150(10)
_cell_formula_units_Z            2
_cell_length_a                   7.45400(10)
_cell_length_b                   7.67710(10)
_cell_length_c                   22.1343(2)
_cell_measurement_reflns_used    36536
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.0130
_cell_measurement_theta_min      4.0470
_cell_volume                     1236.70(3)
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2017)'
_computing_molecular_graphics
;
'ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006)'
;
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015a)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2558
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            60109
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.172
_diffrn_reflns_theta_min         4.054
_exptl_absorpt_coefficient_mu    12.147
_exptl_absorpt_correction_T_max  0.905
_exptl_absorpt_correction_T_min  0.331
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_description       prism
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.203
_exptl_crystal_size_mid          0.051
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.789
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         5159
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0257
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0435P)²+1.3483P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0698
_refine_ls_wR_factor_ref         0.0704
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5039
_reflns_number_total             5159
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00094f2.cif
_cod_data_source_block           shelx_CCDC1
_cod_database_code               7245161
_shelx_shelxl_version_number     2018/3
_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   0.192
_shelx_estimated_absorpt_t_max   0.705
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.95803(2) 1.27107(2) 0.32683(2) 0.02346(6) Uani 1 1 d . . . . .
O1 O 0.7500(3) 0.5568(2) 0.50270(8) 0.0269(4) Uani 1 1 d . . . . .
O2 O 0.6319(3) 0.7696(2) 0.55091(8) 0.0244(4) Uani 1 1 d D . . . .
H2O H 0.601(5) 0.690(3) 0.5732(14) 0.037 Uiso 1 1 d D U . . .
C1 C 0.7180(3) 0.7093(3) 0.50788(11) 0.0195(5) Uani 1 1 d . . . . .
C2 C 0.7726(3) 0.8410(3) 0.46567(11) 0.0187(4) Uani 1 1 d . . . . .
C3 C 0.8556(3) 0.7886(3) 0.41615(11) 0.0214(5) Uani 1 1 d . . . . .
H3 H 0.875772 0.669659 0.409745 0.026 Uiso 1 1 calc R U . . .
C4 C 0.9086(3) 0.9108(3) 0.37620(11) 0.0223(5) Uani 1 1 d . . . . .
H4 H 0.964046 0.875996 0.342175 0.027 Uiso 1 1 calc R U . . .
C5 C 0.8793(3) 1.0848(3) 0.38674(11) 0.0196(5) Uani 1 1 d . . . . .
C6 C 0.7972(3) 1.1391(3) 0.43577(11) 0.0221(5) Uani 1 1 d . . . . .
H6 H 0.778058 1.258381 0.442276 0.027 Uiso 1 1 calc R U . . .
C7 C 0.7436(3) 1.0158(3) 0.47509(11) 0.0213(5) Uani 1 1 d . . . . .
H7 H 0.686593 1.050859 0.508726 0.026 Uiso 1 1 calc R U . . .
S1 S 0.48794(8) 0.53762(7) 0.74501(2) 0.01812(12) Uani 1 1 d . . . . .
S2 S 0.52431(7) 0.57594(7) 0.83872(2) 0.01637(11) Uani 1 1 d . . . . .
O3 O 0.5476(2) 0.5279(2) 0.62638(7) 0.0201(3) Uani 1 1 d . . . . .
O4 O 0.6965(3) 0.3295(2) 0.58349(8) 0.0254(4) Uani 1 1 d D . . . .
H4O H 0.713(5) 0.404(4) 0.5583(13) 0.038 Uiso 1 1 d D U . . .
O5 O 0.5850(2) 0.6760(2) 0.95881(8) 0.0214(3) Uani 1 1 d . . . . .
O6 O 0.3723(2) 0.7606(3) 1.01190(8) 0.0243(4) Uani 1 1 d D . . . .
H6O H 0.460(3) 0.805(4) 1.0383(12) 0.036 Uiso 1 1 d D U . . .
C8 C 0.6061(3) 0.3854(3) 0.62614(10) 0.0174(4) Uani 1 1 d . . . . .
C9 C 0.5805(3) 0.2624(3) 0.67375(10) 0.0165(4) Uani 1 1 d . . . . .
C10 C 0.6133(3) 0.0885(3) 0.66298(11) 0.0206(5) Uani 1 1 d . . . . .
H10 H 0.654540 0.053666 0.625987 0.025 Uiso 1 1 calc R U . . .
C11 C 0.5868(3) -0.0329(3) 0.70498(12) 0.0231(5) Uani 1 1 d . . . . .
H11 H 0.609733 -0.150452 0.697057 0.028 Uiso 1 1 calc R U . . .
C12 C 0.5262(3) 0.0180(3) 0.75903(11) 0.0200(5) Uani 1 1 d . . . . .
H12 H 0.506015 -0.065837 0.787863 0.024 Uiso 1 1 calc R U . . .
C13 C 0.4949(3) 0.1908(3) 0.77139(11) 0.0173(4) Uani 1 1 d . . . . .
H13 H 0.454669 0.224471 0.808707 0.021 Uiso 1 1 calc R U . . .
C14 C 0.5223(3) 0.3143(3) 0.72923(10) 0.0159(4) Uani 1 1 d . . . . .
C15 C 0.3000(3) 0.5317(3) 0.85855(11) 0.0163(4) Uani 1 1 d . . . . .
C16 C 0.1529(3) 0.4417(3) 0.81705(11) 0.0199(5) Uani 1 1 d . . . . .
H16 H 0.171167 0.402107 0.777093 0.024 Uiso 1 1 calc R U . . .
C17 C -0.0213(3) 0.4093(3) 0.83380(12) 0.0242(5) Uani 1 1 d . . . . .
H17 H -0.120330 0.346105 0.805379 0.029 Uiso 1 1 calc R U . . .
C18 C -0.0505(3) 0.4687(4) 0.89161(13) 0.0255(5) Uani 1 1 d . . . . .
H18 H -0.169081 0.446542 0.902898 0.031 Uiso 1 1 calc R U . . .
C19 C 0.0945(3) 0.5606(3) 0.93276(12) 0.0220(5) Uani 1 1 d . . . . .
H19 H 0.074057 0.603490 0.972088 0.026 Uiso 1 1 calc R U . . .
C20 C 0.2708(3) 0.5912(3) 0.91735(11) 0.0171(4) Uani 1 1 d . . . . .
C21 C 0.4251(3) 0.6804(3) 0.96433(11) 0.0177(4) Uani 1 1 d . . . . .
O7 O 0.6409(2) 0.9057(2) 1.09387(8) 0.0246(4) Uani 1 1 d . . . . .
N1 N 0.9498(3) 0.9894(3) 1.11032(9) 0.0204(4) Uani 1 1 d . . . . .
C22 C 0.7942(3) 0.9100(3) 1.07742(11) 0.0210(5) Uani 1 1 d . . . . .
H22 H 0.799742 0.852254 1.038528 0.025 Uiso 1 1 calc R U . . .
C23 C 1.1244(4) 0.9883(4) 1.08794(12) 0.0267(5) Uani 1 1 d . . . . .
H23A H 1.207482 0.933569 1.116837 0.040 Uiso 1 1 calc R U . . .
H23B H 1.179020 1.109744 1.084240 0.040 Uiso 1 1 calc R U . . .
H23C H 1.103835 0.920763 1.047718 0.040 Uiso 1 1 calc R U . . .
C24 C 0.9545(4) 1.0766(4) 1.17096(11) 0.0260(5) Uani 1 1 d . . . . .
H24A H 0.828984 1.079791 1.178857 0.039 Uiso 1 1 calc R U . . .
H24B H 1.019003 1.197388 1.173190 0.039 Uiso 1 1 calc R U . . .
H24C H 1.018825 1.011459 1.201765 0.039 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
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
C1 O2 H2O 111(3) . . ?
O1 C1 O2 123.2(2) . . ?
O1 C1 C2 122.5(2) . . ?
O2 C1 C2 114.3(2) . . ?
C7 C2 C3 120.0(2) . . ?
C7 C2 C1 120.9(2) . . ?
C3 C2 C1 119.2(2) . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 119.1(2) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 121.7(2) . . ?
C6 C5 I1 118.65(18) . . ?
C4 C5 I1 119.65(17) . . ?
C7 C6 C5 118.7(2) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C6 C7 C2 120.6(2) . . ?
C6 C7 H7 119.7 . . ?
C2 C7 H7 119.7 . . ?
C14 S1 S2 104.57(8) . . ?
C15 S2 S1 105.29(8) . . ?
C8 O4 H4O 112(3) . . ?
C21 O6 H6O 112(3) . . ?
O3 C8 O4 123.0(2) . . ?
O3 C8 C9 122.7(2) . . ?
O4 C8 C9 114.4(2) . . ?
C10 C9 C14 119.1(2) . . ?
C10 C9 C8 118.8(2) . . ?
C14 C9 C8 122.1(2) . . ?
C11 C10 C9 121.3(2) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 119.4(2) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C11 C12 C13 120.7(2) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 120.2(2) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C9 119.4(2) . . ?
C13 C14 S1 120.84(17) . . ?
C9 C14 S1 119.77(17) . . ?
C16 C15 C20 119.2(2) . . ?
C16 C15 S2 121.67(18) . . ?
C20 C15 S2 119.10(17) . . ?
C15 C16 C17 120.4(2) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C18 C17 C16 120.4(2) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C17 119.4(2) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C18 C19 C20 121.0(2) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C19 C20 C15 119.4(2) . . ?
C19 C20 C21 119.3(2) . . ?
C15 C20 C21 121.3(2) . . ?
O5 C21 O6 124.1(2) . . ?
O5 C21 C20 122.1(2) . . ?
O6 C21 C20 113.9(2) . . ?
C22 N1 C24 121.3(2) . . ?
C22 N1 C23 121.4(2) . . ?
C24 N1 C23 117.3(2) . . ?
O7 C22 N1 124.6(2) . . ?
O7 C22 H22 117.7 . . ?
N1 C22 H22 117.7 . . ?
N1 C23 H23A 109.5 . . ?
N1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N1 C24 H24A 109.5 . . ?
N1 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N1 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
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 C5 2.100(2) . ?
O1 C1 1.227(3) . ?
O2 C1 1.315(3) . ?
O2 H2O 0.838(10) . ?
C1 C2 1.481(3) . ?
C2 C7 1.394(3) . ?
C2 C3 1.396(3) . ?
C3 C4 1.391(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(3) . ?
C6 C7 1.388(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
S1 C14 1.786(2) . ?
S1 S2 2.0477(8) . ?
S2 C15 1.785(2) . ?
O3 C8 1.230(3) . ?
O4 C8 1.318(3) . ?
O4 H4O 0.838(10) . ?
O5 C21 1.220(3) . ?
O6 C21 1.319(3) . ?
O6 H6O 0.828(10) . ?
C8 C9 1.478(3) . ?
C9 C10 1.400(3) . ?
C9 C14 1.411(3) . ?
C10 C11 1.377(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.394(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(3) . ?
C13 H13 0.9500 . ?
C15 C16 1.392(3) . ?
C15 C20 1.406(3) . ?
C16 C17 1.397(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.386(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.384(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.399(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.488(3) . ?
O7 C22 1.246(3) . ?
N1 C22 1.323(3) . ?
N1 C24 1.452(3) . ?
N1 C23 1.459(3) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
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
O1 C1 C2 C7 -176.2(2) . . . . ?
O2 C1 C2 C7 4.1(3) . . . . ?
O1 C1 C2 C3 3.3(4) . . . . ?
O2 C1 C2 C3 -176.4(2) . . . . ?
C7 C2 C3 C4 -0.2(4) . . . . ?
C1 C2 C3 C4 -179.7(2) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
C3 C4 C5 I1 -179.88(18) . . . . ?
C4 C5 C6 C7 0.1(4) . . . . ?
I1 C5 C6 C7 179.42(18) . . . . ?
C5 C6 C7 C2 0.3(4) . . . . ?
C3 C2 C7 C6 -0.3(4) . . . . ?
C1 C2 C7 C6 179.2(2) . . . . ?
O3 C8 C9 C10 165.6(2) . . . . ?
O4 C8 C9 C10 -14.3(3) . . . . ?
O3 C8 C9 C14 -13.6(4) . . . . ?
O4 C8 C9 C14 166.4(2) . . . . ?
C14 C9 C10 C11 1.1(4) . . . . ?
C8 C9 C10 C11 -178.2(2) . . . . ?
C9 C10 C11 C12 0.1(4) . . . . ?
C10 C11 C12 C13 -0.9(4) . . . . ?
C11 C12 C13 C14 0.6(4) . . . . ?
C12 C13 C14 C9 0.5(3) . . . . ?
C12 C13 C14 S1 -178.54(18) . . . . ?
C10 C9 C14 C13 -1.4(3) . . . . ?
C8 C9 C14 C13 177.9(2) . . . . ?
C10 C9 C14 S1 177.70(18) . . . . ?
C8 C9 C14 S1 -3.0(3) . . . . ?
S2 S1 C14 C13 24.6(2) . . . . ?
S2 S1 C14 C9 -154.46(17) . . . . ?
S1 S2 C15 C16 16.3(2) . . . . ?
S1 S2 C15 C20 -162.97(16) . . . . ?
C20 C15 C16 C17 -0.6(3) . . . . ?
S2 C15 C16 C17 -179.87(18) . . . . ?
C15 C16 C17 C18 1.0(4) . . . . ?
C16 C17 C18 C19 0.0(4) . . . . ?
C17 C18 C19 C20 -1.3(4) . . . . ?
C18 C19 C20 C15 1.7(4) . . . . ?
C18 C19 C20 C21 -176.1(2) . . . . ?
C16 C15 C20 C19 -0.7(3) . . . . ?
S2 C15 C20 C19 178.56(18) . . . . ?
C16 C15 C20 C21 177.0(2) . . . . ?
S2 C15 C20 C21 -3.7(3) . . . . ?
C19 C20 C21 O5 163.3(2) . . . . ?
C15 C20 C21 O5 -14.4(3) . . . . ?
C19 C20 C21 O6 -15.8(3) . . . . ?
C15 C20 C21 O6 166.5(2) . . . . ?
C24 N1 C22 O7 1.7(4) . . . . ?
C23 N1 C22 O7 179.8(2) . . . . ?
