#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/95/2019533.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_2019533
loop_
_publ_author_name
'Zhou, Yu-Jun'
'Lv, Jing'
'Yu, Kai'
'Ma, Jian-Ping'
'Guo, Dian-Shun'
_publ_section_title
;
 Supramolecular structures in three thiouracil derivatives:
 5,6-trimethylene-2-sulfanylidene-1,2-dihydropyrimidin-4(3H)-one,
 2-(4-fluorobenzylsulfanyl)-5,6-trimethylenepyrimidin-4(3H)-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-1H-pyrimidin-4-one
;
_chemical_name_systematic
2-Sulfanylidene-1,2,3,4,6,7-hexahydro-5H-cyclopenta[d]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       'φ and ω'
_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/[σ²(Fo²)+(0.0409P)²+0.0000P] where P=(Fo²+2Fc²)/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>2σ(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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.36128(17) 0.0000 0.2918(4) 0.0437(7) Uani d S 1 2
C C2 0.27896(18) 0.0000 0.5751(4) 0.0451(7) Uani d S 1 2
C C3 0.20538(17) 0.0000 0.4320(4) 0.0426(7) Uani d S 1 2
C C4 0.11486(17) 0.0000 0.4659(5) 0.0525(8) Uani d S 1 2
H H4A 0.1033 0.1025 0.5519 0.063 Uiso d PR 0.50 1
H H4B 0.0993 -0.1196 0.5198 0.063 Uiso d PR 0.50 1
C C6 0.12991(18) 0.0000 0.1049(5) 0.0618(9) Uani d S 1 2
H H6A 0.1197 -0.1195 0.0363 0.074 Uiso d PR 0.50 1
H H6B 0.1263 0.1030 0.0108 0.074 Uiso d PR 0.50 1
C C7 0.21200(17) 0.0000 0.2368(4) 0.0433(7) Uani d S 1 2
C C5 0.0678(3) 0.028(4) 0.2531(6) 0.060(4) Uani d P 0.50 1
H H5A 0.0408 0.1500 0.2371 0.072 Uiso d PR 0.50 1
H H5B 0.0261 -0.0708 0.2289 0.072 Uiso d PR 0.50 1
N N1 0.28795(14) 0.0000 0.1689(3) 0.0485(7) Uani d S 1 2
H H1 0.2891 0.0000 0.0430 0.058 Uiso calc SR 1 2
N N2 0.35355(14) 0.0000 0.4900(3) 0.0477(7) Uani d S 1 2
H H2 0.3993 0.0000 0.5712 0.057 Uiso calc SR 1 2
O O1 0.28256(15) 0.0000 0.7566(3) 0.0689(7) Uani d S 1 2
S S1 0.45269(5) 0.0000 0.20321(12) 0.0657(4) Uani d S 1 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
N1 C1 N2 . . 114.7(2)
N1 C1 S1 . . 121.2(2)
N2 C1 S1 . . 124.1(2)
O1 C2 N2 . . 119.3(3)
O1 C2 C3 . . 127.2(3)
N2 C2 C3 . . 113.5(2)
C7 C3 C2 . . 120.0(2)
C7 C3 C4 . . 111.1(3)
C2 C3 C4 . . 128.8(3)
C3 C4 C5 . 6 102.6(2)
C3 C4 C5 . . 102.6(2)
C5 C4 C5 6 . 14(2)
C3 C4 H4A . . 111.6
C5 C4 H4A 6 . 123.4
C5 C4 H4A . . 111.4
C3 C4 H4B . . 111.6
C5 C4 H4B 6 . 97.4
C5 C4 H4B . . 110.1
H4A C4 H4B . . 109.4
C7 C6 C5 . . 102.3(3)
C7 C6 C5 . 6 102.3(3)
C5 C6 C5 . 6 14(2)
C7 C6 H6A . . 111.7
C5 C6 H6A . . 110.3
C5 C6 H6A 6 . 97.3
C7 C6 H6B . . 111.6
C5 C6 H6B . . 111.1
C5 C6 H6B 6 . 123.3
H6A C6 H6B . . 109.7
C3 C7 N1 . . 122.0(3)
C3 C7 C6 . . 114.1(3)
N1 C7 C6 . . 124.0(3)
C5 C5 C6 6 . 82.8(10)
C5 C5 C4 6 . 82.9(10)
C6 C5 C4 . . 108.5(5)
C5 C5 H5A 6 . 153.1
C6 C5 H5A . . 111.5
C4 C5 H5A . . 111.9
C5 C5 H5B 6 . 44.3
C6 C5 H5B . . 107.8
C4 C5 H5B . . 108.2
H5A C5 H5B . . 108.7
C1 N1 C7 . . 122.7(2)
C1 N1 H1 . . 118.7
C7 N1 H1 . . 118.7
C1 N2 C2 . . 127.2(2)
C1 N2 H2 . . 116.4
C2 N2 H2 . . 116.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 N1 . 1.353(4)
C1 N2 . 1.373(4)
C1 S1 . 1.671(3)
C2 O1 . 1.229(3)
C2 N2 . 1.407(3)
C2 C3 . 1.430(4)
C3 C7 . 1.348(4)
C3 C4 . 1.512(4)
C4 C5 6 1.553(6)
C4 C5 . 1.553(6)
C4 H4A . 0.9600
C4 H4B . 0.9600
C6 C7 . 1.496(4)
C6 C5 . 1.531(6)
C6 C5 6 1.531(6)
C6 H6A . 0.9600
C6 H6B . 0.9600
C7 N1 . 1.370(3)
C5 C5 6 0.38(6)
C5 H5A . 0.9600
C5 H5B . 0.9600
N1 H1 . 0.8600
N2 H2 . 0.8600
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
N1 H1 O1 1_554 0.86 1.94 2.797(4) 175.7
N2 H2 S1 2_656 0.86 2.66 3.516(4) 175.4
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_4
_geom_torsion
O1 C2 C3 C7 . . 180.0
N2 C2 C3 C7 . . 0.0
O1 C2 C3 C4 . . 0.0
N2 C2 C3 C4 . . 180.0
C7 C3 C4 C5 . 6 7.3(11)
C2 C3 C4 C5 . 6 -172.7(11)
C7 C3 C4 C5 . . -7.3(11)
C2 C3 C4 C5 . . 172.7(11)
C2 C3 C7 N1 . . 0.0
C4 C3 C7 N1 . . 180.0
C2 C3 C7 C6 . . 180.0
C4 C3 C7 C6 . . 0.0
C5 C6 C7 C3 . . 7.4(11)
C5 C6 C7 C3 6 . -7.4(11)
C5 C6 C7 N1 . . -172.6(11)
C5 C6 C7 N1 6 . 172.6(11)
C7 C6 C5 C5 . 6 -91.6(2)
C7 C6 C5 C4 . . -11.6(16)
C5 C6 C5 C4 6 . 80.0(14)
C3 C4 C5 C5 . 6 91.6(2)
C3 C4 C5 C6 . . 11.7(16)
C5 C4 C5 C6 6 . -79.9(14)
N2 C1 N1 C7 . . 0.0
S1 C1 N1 C7 . . 180.0
C3 C7 N1 C1 . . 0.0
C6 C7 N1 C1 . . 180.0
N1 C1 N2 C2 . . 0.0
S1 C1 N2 C2 . . 180.0
O1 C2 N2 C1 . . 180.0
C3 C2 N2 C1 . . 0.0
