Three substituted (<i>Z</i>)-5-benzylidene-2-thioxothiazolidin-4-ones: hydrogen-bonded dimers that can be effectively isolated or linked into chains either by aromatic π–π stacking interactions or by dipolar carbonyl–carbonyl interactions
Delgado, Paula; Quiroga, Jairo; de la Torre, Jose M.; Cobo, Justo; Low, John N.; Glidewell, Christopher; Acta Crystallographica Section C 62 (2006) o382–o385; doi:10.1107/S0108270106018038

data_2015459
_publ_section_title
;
 Three substituted (<i>Z</i>)-5-benzylidene-2-thioxothiazolidin-4-ones:
 hydrogen-bonded dimers that can be effectively isolated or linked into
 chains either by aromatic \p--\p stacking interactions or by dipolar
 carbonyl--carbonyl interactions
;
_journal_coeditor_code           SK3027
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o382
_journal_page_last               o385
_journal_paper_doi               10.1107/S0108270106018038
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C13 H13 N O4 S2'
_chemical_formula_moiety         'C13 H13 N O4 S2'
_chemical_formula_sum            'C13 H13 N O4 S2'
_chemical_formula_weight         311.36
_chemical_name_systematic
;
(Z)-5-(3,4,5-Trimethoxybenzylidene)-2-thioxothaolidin-2-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                100.399(2)
_cell_angle_beta                 91.572(2)
_cell_angle_gamma                110.301(2)
_cell_formula_units_Z            4
_cell_length_a                   10.3432(4)
_cell_length_b                   10.9105(4)
_cell_length_c                   13.4621(4)
_cell_measurement_reflns_used    6377
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.73
_cell_volume                     1394.73(9)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997) and COLLECT'
_computing_data_collection       'COLLECT (Hooft, 1999)'
_computing_data_reduction        'DENZO and COLLECT'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 and PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement
'OSCAIL (McArdle, 2003) and SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'Sir2004 (Burla <i>et al.</i>,  2005)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker--Nonius KappaCCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1064
_diffrn_reflns_av_sigmaI/netI    0.1262
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            29714
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.73
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.393
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
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_exptl_crystal_size_mid          0.08
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_refine_diff_density_min         -0.422
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         6377
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1354
_refine_ls_R_factor_gt           0.0632
_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/[\s^2^(Fo^2^)+(0.0539P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_refine_ls_wR_factor_ref         0.1187
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_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            sk3027.cif
_cod_data_source_block           III
_cod_original_cell_volume        1394.72(9)
_cod_database_code               2015459
_cod_database_fobs_code          2015459