#------------------------------------------------------------------------------
#$Date: 2022-07-23 02:30:02 +0300 (Sat, 23 Jul 2022) $
#$Revision: 276813 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/51/7245160.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_7245160
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 Cl O2, C3 H7 N O'
_chemical_formula_sum            'C24 H22 Cl N O7 S2'
_chemical_formula_weight         535.99
_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                94.377(2)
_cell_angle_beta                 100.099(2)
_cell_angle_gamma                97.933(2)
_cell_formula_units_Z            2
_cell_length_a                   7.47300(10)
_cell_length_b                   7.6103(2)
_cell_length_c                   21.7932(4)
_cell_measurement_reflns_used    11220
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.2580
_cell_measurement_theta_min      4.1430
_cell_volume                     1202.10(4)
_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 0.999
_diffrn_measured_fraction_theta_max 0.996
_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  0.0260
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            17234
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.295
_diffrn_reflns_theta_min         4.143
_exptl_absorpt_coefficient_mu    3.436
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.699
_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    1.481
_exptl_crystal_description       slab
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.132
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.027
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4966
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0287
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0361P)²+0.6122P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0746
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4677
_reflns_number_total             4966
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00094f2.cif
_cod_data_source_block           shelx
_cod_database_code               7245160
_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   0.660
_shelx_estimated_absorpt_t_max   0.913
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
Cl1 Cl 0.95196(5) 1.24461(5) 0.33259(2) 0.02537(9) Uani 1 1 d . . . . .
O1 O 0.76068(15) 0.56793(13) 0.50230(5) 0.0242(2) Uani 1 1 d . . . . .
O2 O 0.63922(15) 0.78245(14) 0.54888(5) 0.0224(2) Uani 1 1 d D . . . .
H2O H 0.616(3) 0.703(2) 0.5728(8) 0.034 Uiso 1 1 d D U . . .
C1 C 0.72522(18) 0.72018(18) 0.50601(6) 0.0167(3) Uani 1 1 d . . . . .
C2 C 0.77670(17) 0.85073(18) 0.46257(6) 0.0158(3) Uani 1 1 d . . . . .
C3 C 0.85793(19) 0.79510(19) 0.41286(6) 0.0187(3) Uani 1 1 d . . . . .
H3 H 0.877311 0.674718 0.406822 0.022 Uiso 1 1 calc R U . . .
C4 C 0.91016(19) 0.9159(2) 0.37236(6) 0.0200(3) Uani 1 1 d . . . . .
H4 H 0.964612 0.879100 0.338247 0.024 Uiso 1 1 calc R U . . .
C5 C 0.88179(18) 1.09132(19) 0.38236(6) 0.0189(3) Uani 1 1 d . . . . .
C6 C 0.80033(19) 1.14942(19) 0.43102(7) 0.0200(3) Uani 1 1 d . . . . .
H6 H 0.781258 1.269952 0.436841 0.024 Uiso 1 1 calc R U . . .
C7 C 0.74724(19) 1.02722(19) 0.47107(6) 0.0186(3) Uani 1 1 d . . . . .
H7 H 0.690361 1.064143 0.504554 0.022 Uiso 1 1 calc R U . . .
S1 S 0.47361(5) 0.54578(4) 0.74238(2) 0.01727(8) Uani 1 1 d . . . . .
S2 S 0.51241(4) 0.58605(4) 0.83804(2) 0.01537(8) Uani 1 1 d . . . . .
O3 O 0.55709(14) 0.54155(13) 0.62496(5) 0.0201(2) Uani 1 1 d . . . . .
O4 O 0.71427(16) 0.34493(14) 0.58565(5) 0.0250(2) Uani 1 1 d D . . . .
H4O H 0.719(3) 0.417(2) 0.5589(8) 0.038 Uiso 1 1 d D U . . .
O5 O 0.57587(13) 0.68528(14) 0.96036(5) 0.0209(2) Uani 1 1 d . . . . .
O6 O 0.36356(14) 0.76584(15) 1.01341(5) 0.0229(2) Uani 1 1 d D . . . .
H6O H 0.455(2) 0.810(3) 1.0408(8) 0.034 Uiso 1 1 d D U . . .
C8 C 0.61716(18) 0.39936(18) 0.62625(6) 0.0164(3) Uani 1 1 d . . . . .
C9 C 0.58551(17) 0.27383(17) 0.67327(6) 0.0151(2) Uani 1 1 d . . . . .
C10 C 0.62380(18) 0.10014(18) 0.66308(6) 0.0184(3) Uani 1 1 d . . . . .
H10 H 0.671127 0.066907 0.626904 0.022 Uiso 1 1 calc R U . . .
C11 C 0.59384(19) -0.02377(18) 0.70483(7) 0.0203(3) Uani 1 1 d . . . . .
H11 H 0.620616 -0.141175 0.697535 0.024 Uiso 1 1 calc R U . . .
C12 C 0.52402(18) 0.02539(18) 0.75766(6) 0.0178(3) Uani 1 1 d . . . . .
H12 H 0.501733 -0.059545 0.786271 0.021 Uiso 1 1 calc R U . . .
C13 C 0.48668(17) 0.19704(18) 0.76894(6) 0.0160(3) Uani 1 1 d . . . . .
H13 H 0.439921 0.228951 0.805361 0.019 Uiso 1 1 calc R U . . .
C14 C 0.51714(17) 0.32337(17) 0.72728(6) 0.0142(2) Uani 1 1 d . . . . .
C15 C 0.28899(17) 0.53253(17) 0.85651(6) 0.0150(2) Uani 1 1 d . . . . .
C16 C 0.14196(19) 0.43617(18) 0.81315(7) 0.0190(3) Uani 1 1 d . . . . .
H16 H 0.159667 0.396820 0.772523 0.023 Uiso 1 1 calc R U . . .
C17 C -0.03032(19) 0.3974(2) 0.82905(7) 0.0229(3) Uani 1 1 d . . . . .
H17 H -0.128764 0.329194 0.799523 0.028 Uiso 1 1 calc R U . . .
C18 C -0.05993(19) 0.4574(2) 0.88762(7) 0.0232(3) Uani 1 1 d . . . . .
H18 H -0.178227 0.431582 0.898133 0.028 Uiso 1 1 calc R U . . .
C19 C 0.08491(19) 0.55521(19) 0.93061(7) 0.0202(3) Uani 1 1 d . . . . .
H19 H 0.064430 0.598428 0.970452 0.024 Uiso 1 1 calc R U . . .
C20 C 0.26076(18) 0.59147(17) 0.91635(6) 0.0161(3) Uani 1 1 d . . . . .
C21 C 0.41580(18) 0.68593(18) 0.96522(6) 0.0168(3) Uani 1 1 d . . . . .
O7 O 0.63790(14) 0.91675(14) 1.09826(5) 0.0230(2) Uani 1 1 d . . . . .
N1 N 0.94823(16) 1.00224(15) 1.11548(5) 0.0184(2) Uani 1 1 d . . . . .
C22 C 0.78938(19) 0.92251(18) 1.08144(6) 0.0186(3) Uani 1 1 d . . . . .
H22 H 0.790989 0.865527 1.041248 0.022 Uiso 1 1 calc R U . . .
C23 C 1.1194(2) 1.0040(2) 1.09209(7) 0.0244(3) Uani 1 1 d . . . . .
H23A H 1.207694 0.953157 1.121694 0.037 Uiso 1 1 calc R U . . .
H23B H 1.170304 1.127014 1.087571 0.037 Uiso 1 1 calc R U . . .
H23C H 1.095324 0.932850 1.051261 0.037 Uiso 1 1 calc R U . . .
C24 C 0.9594(2) 1.0885(2) 1.17824(7) 0.0238(3) Uani 1 1 d . . . . .
H24A H 0.835073 1.087932 1.186977 0.036 Uiso 1 1 calc R U . . .
H24B H 1.021330 1.211848 1.181136 0.036 Uiso 1 1 calc R U . . .
H24C H 1.029288 1.023778 1.208894 0.036 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'
Cl Cl 0.3639 0.7018 '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 109.7(14) . . ?
O1 C1 O2 123.15(12) . . ?
O1 C1 C2 122.55(12) . . ?
O2 C1 C2 114.30(11) . . ?
C7 C2 C3 119.95(12) . . ?
C7 C2 C1 121.09(12) . . ?
C3 C2 C1 118.96(12) . . ?
C4 C3 C2 119.88(13) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 119.06(12) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 122.15(13) . . ?
C6 C5 Cl1 118.69(11) . . ?
C4 C5 Cl1 119.17(11) . . ?
C5 C6 C7 118.39(13) . . ?
C5 C6 H6 120.8 . . ?
C7 C6 H6 120.8 . . ?
C6 C7 C2 120.56(12) . . ?
C6 C7 H7 119.7 . . ?
C2 C7 H7 119.7 . . ?
C14 S1 S2 103.97(4) . . ?
C15 S2 S1 105.27(5) . . ?
C8 O4 H4O 109.2(15) . . ?
C21 O6 H6O 110.5(15) . . ?
O3 C8 O4 122.86(12) . . ?
O3 C8 C9 122.91(12) . . ?
O4 C8 C9 114.23(12) . . ?
C10 C9 C14 119.38(12) . . ?
C10 C9 C8 118.50(12) . . ?
C14 C9 C8 122.12(12) . . ?
C11 C10 C9 121.04(13) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 119.27(13) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C13 C12 C11 120.63(12) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.59(12) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C9 119.08(12) . . ?
C13 C14 S1 120.76(10) . . ?
C9 C14 S1 120.16(10) . . ?
C16 C15 C20 119.32(12) . . ?
C16 C15 S2 121.90(10) . . ?
C20 C15 S2 118.77(10) . . ?
C17 C16 C15 120.35(13) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C16 120.66(14) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C19 C18 C17 119.27(13) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C18 C19 C20 121.13(13) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C19 C20 C15 119.23(13) . . ?
C19 C20 C21 119.60(12) . . ?
C15 C20 C21 121.14(11) . . ?
O5 C21 O6 124.22(13) . . ?
O5 C21 C20 121.78(12) . . ?
O6 C21 C20 113.99(11) . . ?
C22 N1 C24 121.35(12) . . ?
C22 N1 C23 121.30(12) . . ?
C24 N1 C23 117.34(12) . . ?
O7 C22 N1 124.76(13) . . ?
O7 C22 H22 117.6 . . ?
N1 C22 H22 117.6 . . ?
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
Cl1 C5 1.7424(14) . ?
O1 C1 1.2236(17) . ?
O2 C1 1.3182(17) . ?
O2 H2O 0.849(9) . ?
C1 C2 1.4822(18) . ?
C2 C7 1.3945(19) . ?
C2 C3 1.3976(19) . ?
C3 C4 1.387(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(2) . ?
C6 C7 1.388(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
S1 C14 1.7842(13) . ?
S1 S2 2.0470(4) . ?
S2 C15 1.7857(13) . ?
O3 C8 1.2278(17) . ?
O4 C8 1.3166(17) . ?
O4 H4O 0.834(10) . ?
O5 C21 1.2199(17) . ?
O6 C21 1.3179(17) . ?
O6 H6O 0.838(10) . ?
C8 C9 1.4799(18) . ?
C9 C10 1.4002(19) . ?
C9 C14 1.4090(18) . ?
C10 C11 1.3826(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.3858(19) . ?
C12 H12 0.9500 . ?
C13 C14 1.3948(18) . ?
C13 H13 0.9500 . ?
C15 C16 1.3949(19) . ?
C15 C20 1.4071(18) . ?
C16 C17 1.390(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.3985(19) . ?
C19 H19 0.9500 . ?
C20 C21 1.4879(19) . ?
O7 C22 1.2458(18) . ?
N1 C22 1.3234(19) . ?
N1 C24 1.4547(17) . ?
N1 C23 1.4564(18) . ?
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 -174.90(13) . . . . ?
O2 C1 C2 C7 4.79(18) . . . . ?
O1 C1 C2 C3 4.4(2) . . . . ?
O2 C1 C2 C3 -175.94(12) . . . . ?
C7 C2 C3 C4 0.4(2) . . . . ?
C1 C2 C3 C4 -178.84(12) . . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
C3 C4 C5 C6 -1.0(2) . . . . ?
C3 C4 C5 Cl1 178.58(11) . . . . ?
C4 C5 C6 C7 0.5(2) . . . . ?
Cl1 C5 C6 C7 -179.05(11) . . . . ?
C5 C6 C7 C2 0.4(2) . . . . ?
C3 C2 C7 C6 -0.9(2) . . . . ?
C1 C2 C7 C6 178.35(13) . . . . ?
O3 C8 C9 C10 166.28(13) . . . . ?
O4 C8 C9 C10 -13.29(18) . . . . ?
O3 C8 C9 C14 -13.2(2) . . . . ?
O4 C8 C9 C14 167.21(12) . . . . ?
C14 C9 C10 C11 0.7(2) . . . . ?
C8 C9 C10 C11 -178.85(12) . . . . ?
C9 C10 C11 C12 0.2(2) . . . . ?
C10 C11 C12 C13 -0.7(2) . . . . ?
C11 C12 C13 C14 0.5(2) . . . . ?
C12 C13 C14 C9 0.37(19) . . . . ?
C12 C13 C14 S1 -178.75(10) . . . . ?
C10 C9 C14 C13 -0.92(19) . . . . ?
C8 C9 C14 C13 178.57(12) . . . . ?
C10 C9 C14 S1 178.20(10) . . . . ?
C8 C9 C14 S1 -2.31(17) . . . . ?
S2 S1 C14 C13 28.05(11) . . . . ?
S2 S1 C14 C9 -151.05(9) . . . . ?
S1 S2 C15 C16 16.15(12) . . . . ?
S1 S2 C15 C20 -163.07(9) . . . . ?
C20 C15 C16 C17 -0.6(2) . . . . ?
S2 C15 C16 C17 -179.77(11) . . . . ?
C15 C16 C17 C18 1.5(2) . . . . ?
C16 C17 C18 C19 -0.6(2) . . . . ?
C17 C18 C19 C20 -1.2(2) . . . . ?
C18 C19 C20 C15 2.2(2) . . . . ?
C18 C19 C20 C21 -175.72(12) . . . . ?
C16 C15 C20 C19 -1.28(19) . . . . ?
S2 C15 C20 C19 177.96(10) . . . . ?
C16 C15 C20 C21 176.60(12) . . . . ?
S2 C15 C20 C21 -4.16(17) . . . . ?
C19 C20 C21 O5 163.14(13) . . . . ?
C15 C20 C21 O5 -14.7(2) . . . . ?
C19 C20 C21 O6 -15.91(18) . . . . ?
C15 C20 C21 O6 166.22(12) . . . . ?
C24 N1 C22 O7 1.7(2) . . . . ?
C23 N1 C22 O7 -179.53(14) . . . . ?
