#------------------------------------------------------------------------------
#$Date: 2020-06-27 08:13:17 +0300 (Sat, 27 Jun 2020) $
#$Revision: 253511 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/34/2243451.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2243451
loop_
_publ_author_name
'Tan, Sang Loon'
'Tiekink, Edward R. T.'
_publ_section_title
;
 2,2'-(Disulfanediyl)dibenzoic acid N,N-dimethylformamide
 monosolvate: crystal structure, Hirshfeld surface analysis and
 computational study
;
_journal_coeditor_code           HB7925
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1150
_journal_page_last               1157
_journal_paper_doi               10.1107/S2056989020008257
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C14 H10 O4 S2, C3 H7 N O'
_chemical_formula_moiety         'C14 H10 O4 S2, C3 H7 N O'
_chemical_formula_sum            'C17 H17 N O5 S2'
_chemical_formula_weight         379.43
_chemical_name_systematic
;
2,2'-(Disulfanediyl)dibenzoic acid N,N-dimethylformamide
monosolvate
;
_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     dual
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                106.1490(10)
_cell_angle_beta                 96.4460(10)
_cell_angle_gamma                100.8840(10)
_cell_formula_units_Z            2
_cell_length_a                   5.05866(4)
_cell_length_b                   12.26170(10)
_cell_length_c                   15.10090(10)
_cell_measurement_reflns_used    13143
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.0280
_cell_measurement_theta_min      3.0710
_cell_volume                     869.944(13)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg,
2006)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2017/1 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2558
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.969
_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  0.0248
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19670
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.271
_diffrn_reflns_theta_min         3.094
_exptl_absorpt_coefficient_mu    3.028
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.316
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2018)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_description       prism
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.063
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.336
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3543
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0256
_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)+(0.0405P)²+0.3204P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0714
_refine_ls_wR_factor_ref         0.0720
_reflns_number_gt                3410
_reflns_number_total             3543
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7925sup1.cif
_cod_data_source_block           I
_cod_database_code               2243451
_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   0.530
_shelx_estimated_absorpt_t_max   0.832
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.13127(6) 0.80270(2) 0.28401(2) 0.01841(9) Uani d 1 . .
S S2 -0.10332(6) 0.84945(2) 0.18710(2) 0.01848(9) Uani d 1 . .
O O1 0.32810(18) 0.61831(8) 0.48410(6) 0.02255(19) Uani d 1 . .
H H1O 0.480(2) 0.6544(14) 0.5192(11) 0.034 Uiso d 1 . .
O O2 0.42509(17) 0.76207(8) 0.41991(6) 0.02129(19) Uani d 1 . .
O O3 -0.30085(18) 0.92323(8) -0.07873(6) 0.02025(19) Uani d 1 . .
H H3O -0.403(3) 0.9709(12) -0.0714(12) 0.030 Uiso d 1 . .
O O4 -0.37132(17) 0.93328(7) 0.06697(6) 0.01850(18) Uani d 1 . .
O O5 0.78590(18) 0.72556(8) 0.59804(6) 0.0248(2) Uani d 1 . .
N N1 1.1659(2) 0.87050(9) 0.62312(7) 0.0212(2) Uani d 1 . .
C C1 0.2742(2) 0.67339(10) 0.42316(8) 0.0176(2) Uani d 1 . .
C C2 0.0090(2) 0.61916(10) 0.35774(8) 0.0170(2) Uani d 1 . .
C C3 -0.0765(2) 0.67004(10) 0.28992(8) 0.0166(2) Uani d 1 . .
C C4 -0.3247(2) 0.61624(11) 0.22897(9) 0.0193(2) Uani d 1 . .
H H4 -0.380732 0.647747 0.181123 0.023 Uiso calc 1 . .
C C5 -0.4903(2) 0.51701(11) 0.23773(9) 0.0213(3) Uani d 1 . .
H H5 -0.660717 0.482386 0.196749 0.026 Uiso calc 1 . .
C C6 -0.4093(3) 0.46787(11) 0.30573(9) 0.0219(3) Uani d 1 . .
H H6 -0.524200 0.400478 0.311867 0.026 Uiso calc 1 . .
C C7 -0.1591(3) 0.51829(11) 0.36451(8) 0.0204(2) Uani d 1 . .
H H7 -0.100899 0.483843 0.410105 0.024 Uiso calc 1 . .
C C8 -0.0191(2) 0.77686(10) 0.07734(8) 0.0165(2) Uani d 1 . .
C C9 -0.0966(2) 0.80827(10) -0.00313(8) 0.0156(2) Uani d 1 . .
C C10 -0.0139(2) 0.75656(11) -0.08709(9) 0.0192(2) Uani d 1 . .
H H10 -0.062982 0.779179 -0.140805 0.023 Uiso calc 1 . .
C C11 0.1383(3) 0.67300(11) -0.09306(9) 0.0222(3) Uani d 1 . .
H H11 0.196005 0.639201 -0.150100 0.027 Uiso calc 1 . .
C C12 0.2057(3) 0.63912(11) -0.01461(9) 0.0225(3) Uani d 1 . .
H H12 0.306044 0.580290 -0.018626 0.027 Uiso calc 1 . .
C C13 0.1282(2) 0.69023(11) 0.06944(9) 0.0200(2) Uani d 1 . .
H H13 0.175946 0.665950 0.122388 0.024 Uiso calc 1 . .
C C14 -0.2676(2) 0.89386(10) -0.00130(8) 0.0152(2) Uani d 1 . .
C C15 0.9281(2) 0.80364(11) 0.57469(9) 0.0207(2) Uani d 1 . .
H H15 0.861275 0.816264 0.517895 0.025 Uiso calc 1 . .
C C16 1.2863(3) 0.85536(13) 0.70996(9) 0.0282(3) Uani d 1 . .
H H16A 1.268974 0.919308 0.763221 0.042 Uiso calc 1 . .
H H16B 1.480062 0.855771 0.709563 0.042 Uiso calc 1 . .
H H16C 1.190793 0.780820 0.715480 0.042 Uiso calc 1 . .
C C17 1.3127(3) 0.96362(12) 0.59254(10) 0.0281(3) Uani d 1 . .
H H17A 1.220139 0.959343 0.530664 0.042 Uiso calc 1 . .
H H17B 1.500247 0.954934 0.588962 0.042 Uiso calc 1 . .
H H17C 1.316721 1.039287 0.637404 0.042 Uiso calc 1 . .
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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 S1 S2 . . 104.21(4) ?
C8 S2 S1 . . 104.44(4) ?
C1 O1 H1O . . 109.1(12) ?
C14 O3 H3O . . 107.5(11) ?
C15 N1 C17 . . 121.01(11) ?
C15 N1 C16 . . 121.21(11) ?
C17 N1 C16 . . 117.77(11) ?
O2 C1 O1 . . 123.78(11) ?
O2 C1 C2 . . 121.86(11) ?
O1 C1 C2 . . 114.35(10) ?
C7 C2 C3 . . 119.58(11) ?
C7 C2 C1 . . 120.03(11) ?
C3 C2 C1 . . 120.37(11) ?
C4 C3 C2 . . 118.92(11) ?
C4 C3 S1 . . 121.24(9) ?
C2 C3 S1 . . 119.84(9) ?
C5 C4 C3 . . 120.53(11) ?
C5 C4 H4 . . 119.7 ?
C3 C4 H4 . . 119.7 ?
C4 C5 C6 . . 120.71(11) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C7 C6 C5 . . 119.22(11) ?
C7 C6 H6 . . 120.4 ?
C5 C6 H6 . . 120.4 ?
C6 C7 C2 . . 120.98(12) ?
C6 C7 H7 . . 119.5 ?
C2 C7 H7 . . 119.5 ?
C13 C8 C9 . . 118.50(11) ?
C13 C8 S2 . . 121.28(9) ?
C9 C8 S2 . . 120.20(9) ?
C10 C9 C8 . . 119.71(11) ?
C10 C9 C14 . . 118.89(10) ?
C8 C9 C14 . . 121.39(10) ?
C11 C10 C9 . . 120.98(11) ?
C11 C10 H10 . . 119.5 ?
C9 C10 H10 . . 119.5 ?
C10 C11 C12 . . 119.16(11) ?
C10 C11 H11 . . 120.4 ?
C12 C11 H11 . . 120.4 ?
C11 C12 C13 . . 120.69(11) ?
C11 C12 H12 . . 119.7 ?
C13 C12 H12 . . 119.7 ?
C12 C13 C8 . . 120.87(12) ?
C12 C13 H13 . . 119.6 ?
C8 C13 H13 . . 119.6 ?
O4 C14 O3 . . 123.20(10) ?
O4 C14 C9 . . 122.27(10) ?
O3 C14 C9 . . 114.53(10) ?
O5 C15 N1 . . 124.80(12) ?
O5 C15 H15 . . 117.6 ?
N1 C15 H15 . . 117.6 ?
N1 C16 H16A . . 109.5 ?
N1 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
N1 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
N1 C17 H17A . . 109.5 ?
N1 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
N1 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C3 . 1.7929(12) ?
S1 S2 . 2.0524(4) ?
S2 C8 . 1.7894(12) ?
O1 C1 . 1.3177(15) ?
O1 H1O . 0.845(9) ?
O2 C1 . 1.2216(15) ?
O3 C14 . 1.3184(14) ?
O3 H3O . 0.845(9) ?
O4 C14 . 1.2295(14) ?
O5 C15 . 1.2423(16) ?
N1 C15 . 1.3228(17) ?
N1 C17 . 1.4557(17) ?
N1 C16 . 1.4573(17) ?
C1 C2 . 1.4893(16) ?
C2 C7 . 1.3985(17) ?
C2 C3 . 1.4082(17) ?
C3 C4 . 1.3958(17) ?
C4 C5 . 1.3889(18) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.3885(18) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.3853(18) ?
C6 H6 . 0.9500 ?
C7 H7 . 0.9500 ?
C8 C13 . 1.3951(16) ?
C8 C9 . 1.4103(16) ?
C9 C10 . 1.3988(16) ?
C9 C14 . 1.4772(15) ?
C10 C11 . 1.3831(17) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.3887(18) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.3855(18) ?
C12 H12 . 0.9500 ?
C13 H13 . 0.9500 ?
C15 H15 . 0.9500 ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 0.9800 ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1O O5 . 0.847(14) 1.753(14) 2.5981(13) 176.0(17)
O3 H3O O4 2_475 0.844(16) 1.780(16) 2.6215(13) 174.9(17)
C15 H15 O2 . 0.95 2.38 3.1162(15) 134
C7 H7 O1 2_566 0.95 2.53 3.2850(16) 136
C1 O2 Cg1 1_655 1.2216(15) 3.4181(10) 3.4843(12) 82.88(7)
C14 O4 Cg2 1_455 1.2295(14) 3.3281(10) 3.6227(12) 93.76(7)
C11 H11 Cg1 2_565 0.95 2.94 3.7962(14) 150
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 C1 C2 C7 . . . . -179.30(11) ?
O1 C1 C2 C7 . . . . 0.13(16) ?
O2 C1 C2 C3 . . . . -0.45(17) ?
O1 C1 C2 C3 . . . . 178.99(10) ?
C7 C2 C3 C4 . . . . -1.89(17) ?
C1 C2 C3 C4 . . . . 179.25(10) ?
C7 C2 C3 S1 . . . . 177.41(9) ?
C1 C2 C3 S1 . . . . -1.45(15) ?
S2 S1 C3 C4 . . . . 6.15(10) ?
S2 S1 C3 C2 . . . . -173.13(8) ?
C2 C3 C4 C5 . . . . 2.79(17) ?
S1 C3 C4 C5 . . . . -176.49(9) ?
C3 C4 C5 C6 . . . . -1.54(18) ?
C4 C5 C6 C7 . . . . -0.67(18) ?
C5 C6 C7 C2 . . . . 1.57(18) ?
C3 C2 C7 C6 . . . . -0.29(18) ?
C1 C2 C7 C6 . . . . 178.58(11) ?
S1 S2 C8 C13 . . . . 12.35(11) ?
S1 S2 C8 C9 . . . . -166.35(8) ?
C13 C8 C9 C10 . . . . -3.03(17) ?
S2 C8 C9 C10 . . . . 175.70(9) ?
C13 C8 C9 C14 . . . . 176.08(10) ?
S2 C8 C9 C14 . . . . -5.18(15) ?
C8 C9 C10 C11 . . . . 1.39(18) ?
C14 C9 C10 C11 . . . . -177.74(11) ?
C9 C10 C11 C12 . . . . 0.97(18) ?
C10 C11 C12 C13 . . . . -1.66(19) ?
C11 C12 C13 C8 . . . . -0.04(19) ?
C9 C8 C13 C12 . . . . 2.38(18) ?
S2 C8 C13 C12 . . . . -176.34(9) ?
C10 C9 C14 O4 . . . . 172.13(11) ?
C8 C9 C14 O4 . . . . -6.99(17) ?
C10 C9 C14 O3 . . . . -7.31(15) ?
C8 C9 C14 O3 . . . . 173.56(10) ?
C17 N1 C15 O5 . . . . -177.13(12) ?
C16 N1 C15 O5 . . . . 1.3(2) ?

_cod_database_fobs_code 2243451
