Supramolecular structures in three thiouracil derivatives: 5,6-trimethylene-2-sulfanylidene-1,2-dihydropyrimidin-4(3<i>H</i>)-one, 2-(4-fluorobenzylsulfanyl)-5,6-trimethylenepyrimidin-4(3<i>H</i>)-one and methyl 2-{[2-(4-fluorobenzylsulfanyl)-5,6-trimethylenepyrimidin-4-yl]oxy}acetate
Zhou, Yu-Jun; Lv, Jing; Yu, Kai; Ma, Jian-Ping; Guo, Dian-Shun; Acta Crystallographica Section C 70 (2014) 416–420; doi:10.1107/S2053229614006111

data_2019533
_publ_section_title
;
 Supramolecular structures in three thiouracil derivatives:
 5,6-trimethylene-2-sulfanylidene-1,2-dihydropyrimidin-4(3<i>H</i>)-one,
 2-(4-fluorobenzylsulfanyl)-5,6-trimethylenepyrimidin-4(3<i>H</i>)-one and
 methyl
 2-{[2-(4-fluorobenzylsulfanyl)-5,6-trimethylenepyrimidin-4-yl]oxy}acetate
;
_journal_coeditor_code           SF3223
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              416
_journal_page_last               420
_journal_paper_doi               10.1107/S2053229614006111
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C7 H8 N2 O S'
_chemical_formula_moiety         'C7 H8 N2 O S'
_chemical_formula_sum            'C7 H8 N2 O S'
_chemical_formula_weight         168.21
_chemical_name_common
;
5,6-Trimethylene-2-sulfanylidene-1<i>H</i>-pyrimidin-4-one
;
_chemical_name_systematic
2-Sulfanylidene-1,2,3,4,6,7-hexahydro-5<i>H</i>-cyclopenta[<i>d</i>]pyrimidin-4-one
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.935(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.158(15)
_cell_length_b                   6.986(6)
_cell_length_c                   6.810(6)
_cell_measurement_temperature    293(2)
_cell_volume                     761.4(12)
_computing_cell_refinement       'SMART (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXS97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       '\f and \w'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0903
_diffrn_reflns_av_sigmaI/netI    0.0687
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2052
_diffrn_reflns_theta_full        25.98
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_min         2.55
_exptl_absorpt_coefficient_mu    0.362
_exptl_absorpt_correction_T_max  0.897
_exptl_absorpt_correction_T_min  0.870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.254
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     70
_refine_ls_number_reflns         810
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.959
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0420
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0409P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.1046
_reflns_number_gt                550
_reflns_number_total             810
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            sf3223sup1.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               2019533
_cod_database_fobs_code          2019533