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_2019535
_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          'C17 H17 F N2 O3 S'
_chemical_formula_moiety         'C17 H17 F N2 O3 S'
_chemical_formula_sum            'C17 H17 F N2 O3 S'
_chemical_formula_weight         348.39
_chemical_name_common
;
2-(4-Fluorobenzylsulfanyl)-4-(methoxycarboxymethoxy)-5,6-trimethylenepyrimidine
;
_chemical_name_systematic
'Methyl 2-({2-[(4-fluorobenzyl)sulfanyl]-6,7-dihydro-5<i>H</i>-cyclopenta[<i>d</i>]pyrimidin-4-yl}oxy)acetate'
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'I -2ya'
_symmetry_space_group_name_H-M   'I 1 a 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.045(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.1673(12)
_cell_length_b                   8.1187(5)
_cell_length_c                   23.7393(16)
_cell_measurement_reflns_used    4673
_cell_measurement_temperature    99.95(13)
_cell_measurement_theta_max      28.1270
_cell_measurement_theta_min      3.6350
_cell_volume                     3235.8(4)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2012)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2012)'
_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      99.95(13)
_diffrn_detector_area_resol_mean 16.0793
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Agilent SuperNova Dual diffractometer (Cu at zero) with Eos detector'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0628
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11191
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.1199
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 1
_diffrn_standards_interval_time  5
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  0.9797
_exptl_absorpt_correction_T_min  0.9408
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.197
_refine_ls_abs_structure_details 'Flack (1983), with 2105 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.10(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         4963
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0350P)^2^+1.9371P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.0864
_reflns_number_gt                4626
_reflns_number_total             4963
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            sf3223sup1.cif
_cod_data_source_block           3
_cod_original_sg_symbol_H-M      'I a'
_cod_database_code               2019535
_cod_database_fobs_code          2019535