#------------------------------------------------------------------------------
#$Date: 2020-08-12 07:47:51 +0300 (Wed, 12 Aug 2020) $
#$Revision: 255253 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/35/2243530.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_2243530
loop_
_publ_author_name
'Cordero Giménez, Keysha T.'
'Soto Díaz, Victoria Y.'
'González Espiet, Jean C.'
'Levín Flores, Alexis'
'Bas Concepción, Jesbaniris'
'Rivera Cruz, Kevin E.'
'Rodríguez Ayala, Dara L.'
'Piñero Cruz, Dalice M.'
_publ_section_title
;
 Crystal structure, Hirshfeld surface analysis and spectroscopic
 characterization of the di-enol tautomeric form of the compound
 3,3'-[(2-sulfanylidene-1,3-dithiole-4,5-diyl)bis(sulfanediyl)]bis(pentane-2,4-dione)
;
_journal_coeditor_code           DX2025
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1427
_journal_page_last               1432
_journal_paper_doi               10.1107/S2056989020010695
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C13 H14 O4 S5'
_chemical_formula_moiety         'C13 H14 O4 S5'
_chemical_formula_sum            'C13 H14 O4 S5'
_chemical_formula_weight         394.54
_chemical_name_systematic
(3E,3'E)-3,3'-[(2-Sulfanylidene-1,3-dithiole-4,5-diyl)bis(sulfanediyl)]bis(4-hydroxypent-3-en-2-one)
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                84.3190(10)
_cell_angle_beta                 83.5740(10)
_cell_angle_gamma                69.1510(10)
_cell_formula_units_Z            2
_cell_length_a                   7.18430(10)
_cell_length_b                   9.91980(10)
_cell_length_c                   12.5230(2)
_cell_measurement_reflns_used    38605
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.8680
_cell_measurement_theta_min      3.5510
_cell_volume                     827.11(2)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
ShelXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014/5 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku SuperNova HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            45972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.096
_diffrn_reflns_theta_min         3.559
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.588
_exptl_absorpt_correction_T_max  0.673
_exptl_absorpt_correction_T_min  0.208
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2015)
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.311
_refine_ls_extinction_coef       0.0023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL-2016/6 (Sheldrick 2015b)
;
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3072
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0265
_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)+(0.0432P)²+0.5496P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0722
_refine_ls_wR_factor_ref         0.0725
_reflns_number_gt                3034
_reflns_number_total             3086
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            dx2025sup1.cif
_cod_data_source_block           I
_cod_database_code               2243530
_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   0.243
_shelx_estimated_absorpt_t_max   0.693
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 0.23650(6) 0.66587(4) 0.42463(3) 0.01782(12) Uani d 1 . .
S S2 0.27692(6) 0.63562(4) 0.65943(3) 0.01461(11) Uani d 1 . .
S S3 0.31242(6) 0.48313(4) 0.88104(3) 0.01525(12) Uani d 1 . .
S S4 0.24878(6) 0.21427(4) 0.76744(3) 0.01430(11) Uani d 1 . .
S S5 0.22936(6) 0.40181(4) 0.55835(3) 0.01485(11) Uani d 1 . .
O O1 0.58163(18) 0.77059(13) 0.86405(10) 0.0219(3) Uani d 1 . .
O O2 0.22982(18) 0.89341(12) 0.91407(10) 0.0208(3) Uani d 1 . .
H H2 0.348293 0.879765 0.896703 0.031 Uiso calc 1 . .
O O3 0.79489(17) -0.06088(12) 0.69638(10) 0.0204(3) Uani d 1 . .
O O4 0.56236(18) -0.12438(12) 0.60106(10) 0.0212(3) Uani d 1 . .
H H4 0.667516 -0.126626 0.622140 0.032 Uiso calc 1 . .
C C1 0.2480(2) 0.57110(16) 0.54050(13) 0.0137(3) Uani d 1 . .
C C2 0.2827(2) 0.48345(16) 0.74276(13) 0.0129(3) Uani d 1 . .
C C3 0.2616(2) 0.37325(16) 0.69608(13) 0.0129(3) Uani d 1 . .
C C4 0.7301(3) 0.5227(2) 0.83018(15) 0.0232(4) Uani d 1 . .
H H4A 0.728193 0.505999 0.756173 0.035 Uiso calc 1 . .
H H4B 0.725804 0.439335 0.874947 0.035 Uiso calc 1 . .
H H4C 0.850316 0.540141 0.839425 0.035 Uiso calc 1 . .
C C5 0.5532(3) 0.65102(18) 0.86127(13) 0.0175(3) Uani d 1 . .
C C6 0.3570(2) 0.64631(17) 0.88533(13) 0.0146(3) Uani d 1 . .
C C7 0.1978(2) 0.77374(18) 0.91381(13) 0.0163(3) Uani d 1 . .
C C8 -0.0110(3) 0.78032(18) 0.94305(15) 0.0206(4) Uani d 1 . .
H H8A -0.080210 0.861593 0.985597 0.031 Uiso calc 1 . .
H H8B -0.010564 0.692988 0.983764 0.031 Uiso calc 1 . .
H H8C -0.077272 0.790640 0.878697 0.031 Uiso calc 1 . .
C C9 0.6980(3) 0.13033(18) 0.81362(15) 0.0213(4) Uani d 1 . .
H H9A 0.632959 0.118292 0.883274 0.032 Uiso calc 1 . .
H H9B 0.650861 0.230598 0.789056 0.032 Uiso calc 1 . .
H H9C 0.839859 0.097756 0.818419 0.032 Uiso calc 1 . .
C C10 0.6520(2) 0.04366(17) 0.73592(14) 0.0170(3) Uani d 1 . .
C C11 0.4523(2) 0.07528(16) 0.70716(13) 0.0148(3) Uani d 1 . .
C C12 0.4160(2) -0.01363(17) 0.63824(14) 0.0168(3) Uani d 1 . .
C C13 0.2157(3) 0.00525(18) 0.60412(15) 0.0203(4) Uani d 1 . .
H H13A 0.231343 -0.053312 0.544829 0.030 Uiso calc 1 . .
H H13B 0.148642 0.104954 0.582310 0.030 Uiso calc 1 . .
H H13C 0.137979 -0.023707 0.663218 0.030 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'
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
C2 S2 C1 . . 97.02(7) ?
C6 S3 C2 . . 101.45(7) ?
C3 S4 C11 . . 103.72(7) ?
C1 S5 C3 . . 97.48(7) ?
C7 O2 H2 . . 109.5 ?
C12 O4 H4 . . 109.5 ?
S1 C1 S2 . . 122.31(9) ?
S1 C1 S5 . . 124.58(10) ?
S5 C1 S2 . . 113.10(9) ?
S2 C2 S3 . . 118.79(9) ?
C3 C2 S2 . . 116.65(13) ?
C3 C2 S3 . . 124.56(13) ?
S5 C3 S4 . . 120.39(9) ?
C2 C3 S4 . . 123.78(13) ?
C2 C3 S5 . . 115.69(12) ?
H4A C4 H4B . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
C5 C4 H4A . . 109.5 ?
C5 C4 H4B . . 109.5 ?
C5 C4 H4C . . 109.5 ?
O1 C5 C4 . . 117.29(15) ?
O1 C5 C6 . . 119.46(15) ?
C6 C5 C4 . . 123.24(15) ?
C5 C6 S3 . . 120.55(12) ?
C7 C6 S3 . . 120.13(12) ?
C7 C6 C5 . . 119.32(14) ?
O2 C7 C6 . . 119.97(15) ?
O2 C7 C8 . . 116.18(15) ?
C6 C7 C8 . . 123.84(15) ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8B . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
H9A C9 H9B . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C10 C9 H9A . . 109.5 ?
C10 C9 H9B . . 109.5 ?
C10 C9 H9C . . 109.5 ?
O3 C10 C9 . . 118.05(15) ?
O3 C10 C11 . . 120.25(15) ?
C11 C10 C9 . . 121.69(14) ?
C10 C11 S4 . . 120.87(12) ?
C12 C11 S4 . . 119.52(12) ?
C12 C11 C10 . . 119.34(14) ?
O4 C12 C11 . . 120.13(15) ?
O4 C12 C13 . . 115.14(14) ?
C11 C12 C13 . . 124.71(15) ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13B . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 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 C1 . 1.6424(17) ?
S2 C1 . 1.7389(16) ?
S2 C2 . 1.7385(16) ?
S3 C2 . 1.7679(16) ?
S3 C6 . 1.7653(16) ?
S4 C3 . 1.7608(16) ?
S4 C11 . 1.7700(16) ?
S5 C1 . 1.7225(16) ?
S5 C3 . 1.7479(16) ?
O1 C5 . 1.278(2) ?
O2 H2 . 0.8200 ?
O2 C7 . 1.287(2) ?
O3 C10 . 1.267(2) ?
O4 H4 . 0.8200 ?
O4 C12 . 1.303(2) ?
C2 C3 . 1.351(2) ?
C4 H4A . 0.9600 ?
C4 H4B . 0.9600 ?
C4 H4C . 0.9600 ?
C4 C5 . 1.491(2) ?
C5 C6 . 1.424(2) ?
C6 C7 . 1.415(2) ?
C7 C8 . 1.483(2) ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C9 C10 . 1.495(2) ?
C10 C11 . 1.435(2) ?
C11 C12 . 1.399(2) ?
C12 C13 . 1.489(2) ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
C10 O1 3.178(2) 1_545 y
C12 O4 3.180(2) 2_656 y
C13 O4 3.219(2) 2_656 y
S3 C5 3.471(2) 2_667 y
S5 S5 3.5688(6) 2_566 y
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
O2 H2 O1 . 0.82 1.67 2.4228(17) 151
O4 H4 O3 . 0.82 1.69 2.4406(17) 151
C13 H13C O3 1_455 0.96 2.60 3.374(3) 138
C8 H8C O3 1_465 0.96 2.66 3.522(2) 150
C8 H8A O2 2_577 0.96 2.66 3.612(2) 170
C8 H8C O1 1_455 0.96 2.56 3.228(3) 127
C9 H9B S1 2_666 0.96 2.90 3.5184(19) 123
C13 H13B S1 2_566 0.96 2.89 3.7165(19) 144
C4 H4A S1 2_666 0.96 2.90 3.7987(19) 156
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
S2 C2 C3 S4 . . . . -176.18(8) ?
S2 C2 C3 S5 . . . . -0.54(18) ?
S3 C2 C3 S4 . . . . 3.1(2) ?
S3 C2 C3 S5 . . . . 178.72(8) ?
S3 C6 C7 O2 . . . . -178.14(12) ?
S3 C6 C7 C8 . . . . 1.0(2) ?
S4 C11 C12 O4 . . . . -173.78(12) ?
S4 C11 C12 C13 . . . . 4.5(2) ?
O1 C5 C6 S3 . . . . 179.45(12) ?
O1 C5 C6 C7 . . . . -1.1(2) ?
O3 C10 C11 S4 . . . . 176.35(12) ?
O3 C10 C11 C12 . . . . 2.3(2) ?
C1 S2 C2 S3 . . . . 179.61(9) ?
C1 S2 C2 C3 . . . . -1.09(14) ?
C1 S5 C3 S4 . . . . 177.69(10) ?
C1 S5 C3 C2 . . . . 1.89(14) ?
C2 S2 C1 S1 . . . . -178.63(10) ?
C2 S2 C1 S5 . . . . 2.31(10) ?
C2 S3 C6 C5 . . . . -84.62(14) ?
C2 S3 C6 C7 . . . . 95.98(14) ?
C3 S4 C11 C10 . . . . 80.09(14) ?
C3 S4 C11 C12 . . . . -105.92(14) ?
C3 S5 C1 S1 . . . . 178.43(11) ?
C3 S5 C1 S2 . . . . -2.54(10) ?
C4 C5 C6 S3 . . . . 0.8(2) ?
C4 C5 C6 C7 . . . . -179.82(15) ?
C5 C6 C7 O2 . . . . 2.4(2) ?
C5 C6 C7 C8 . . . . -178.41(15) ?
C6 S3 C2 S2 . . . . -6.57(11) ?
C6 S3 C2 C3 . . . . 174.19(14) ?
C9 C10 C11 S4 . . . . -2.8(2) ?
C9 C10 C11 C12 . . . . -176.84(15) ?
C10 C11 C12 O4 . . . . 0.3(2) ?
C10 C11 C12 C13 . . . . 178.60(15) ?
C11 S4 C3 S5 . . . . 63.50(11) ?
C11 S4 C3 C2 . . . . -121.05(15) ?

_cod_database_fobs_code 2243530
