##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_audit_creation_method     'SHELXL-97'
_journal_date_recd_electronic     2004-09-20
_journal_date_accepted     2004-09-24
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2004
_journal_volume     60
_journal_issue     10
_journal_page_first     o1909
_journal_page_last     o1910
_journal_paper_category     EO
_publ_contact_author_name     'Hua-Zheng Yang'
_publ_contact_author_address
;
State Key Laboratory and Institute of Elemento-Organic Chemistry
Nankai University
Tianjin
Weijin Road No 94 ,Tianjin
China
;
_publ_contact_author_email     chshengyao@mail.nankai.edu.cn
_publ_contact_author_fax     '022-23503438'
_publ_contact_author_phone     '022-23503799'
_publ_section_title
;
3-(4-Fluorobenzyl)-2-thioxo-3,4,5,6-tetrahydropyrimidin-4(1H)-one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Chang-Sheng Yao' .
;
State Key Laboratory and Institute of Elemento-Organic Chemistry
Nankai University
Weijin Road No 94
Tianjin
People's Republic of China
;
    'Hai-Bin Song' .
;
State Key Laboratory and Institute of Elemento-Organic Chemistry
Nankai University
Weijin Road No 94
Tianjin
People's Republic of China
;
    'You-Quan Zhu' .
;
State Key Laboratory and Institute of Elemento-Organic Chemistry
Nankai University
Weijin Road No 94
Tianjin
People's Republic of China
;
    'Ying Gao' .
;
State Key Laboratory and Institute of Elemento-Organic Chemistry
Nankai University
Weijin Road No 94
Tianjin
People's Republic of China
;
    'Fang-Zhong Hu' .
;
State Key Laboratory and Institute of Elemento-Organic Chemistry
Nankai University
Weijin Road No 94
Tianjin
People's Republic of China
;
    'Xiao-Mao Zou' .
;
State Key Laboratory and Institute of Elemento-Organic Chemistry
Nankai University
Weijin Road No 94
Tianjin
People's Republic of China
;
    'Hua-Zheng Yang' .
;
State Key Laboratory and Institute of Elemento-Organic Chemistry
Nankai University
Weijin Road No 94
Tianjin
People's Republic of China
;
data_I
_chemical_name_systematic
;
3-(4-Fluorobenzyl)-2-thioxo-3,4,5,6-tetrahydropyrimidin-4(1H)-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H11 F N2 O S'
_chemical_formula_sum     'C11 H11 F N2 O S'
_chemical_formula_iupac     'C11 H11 F N2 O S'
_chemical_formula_weight     238.28
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     6.392(3)
_cell_length_b     9.081(4)
_cell_length_c     11.099(5)
_cell_angle_alpha     113.793(6)
_cell_angle_beta     95.328(7)
_cell_angle_gamma     99.931(6)
_cell_volume     571.2(4)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1012
_cell_measurement_theta_min     3.29
_cell_measurement_theta_max     26.53
_cell_measurement_temperature     293(2)
_exptl_crystal_description     'prism'
_exptl_crystal_colour     'colorless'
_exptl_crystal_size_max     0.22
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.18
_exptl_crystal_density_diffrn     1.385
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     248
_exptl_absorpt_coefficient_mu     0.276
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.772281
_exptl_absorpt_correction_T_max     1.000000
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     2984
_diffrn_reflns_av_R_equivalents     0.0142
_diffrn_reflns_av_sigmaI/netI     0.0223
_diffrn_reflns_theta_min     2.04
_diffrn_reflns_theta_max     25.01
_diffrn_reflns_theta_full     25.01
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -8
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2005
_reflns_number_gt     1725
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0393
_refine_ls_R_factor_gt     0.0323
_refine_ls_wR_factor_gt     0.0893
_refine_ls_wR_factor_ref     0.0957
_refine_ls_goodness_of_fit_ref     1.066
_refine_ls_restrained_S_all     1.066
_refine_ls_number_reflns     2005
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.0482P)²+0.1179P] where P = (Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.005
_refine_ls_shift/su_mean     0.001
_refine_diff_density_max     0.203
_refine_diff_density_min     -0.155
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    'F' 'F' 0.0171 0.0103
                         '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'
_computing_data_collection     'SMART (Bruker 1998)'
_computing_cell_refinement     'SAINT'
_computing_data_reduction     'SAINT (Bruker 1999)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker 1999)'
_computing_publication_material     'SHELXTL'
loop_
    _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_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    S1 0.35303(8) 0.61796(6) 0.68031(5) 0.05809(18) Uani d . 1 . . S
    F1 0.1921(3) 1.45690(18) 1.08069(15) 0.1217(6) Uani d . 1 . . F
    O1 -0.18352(19) 0.84740(16) 0.49968(13) 0.0596(4) Uani d . 1 . . O
    N1 0.3494(2) 0.67526(19) 0.46645(15) 0.0537(4) Uani d . 1 . . N
    H1A 0.4657 0.6308 0.4631 0.064 Uiso d R 1 . . H
    N2 0.0787(2) 0.75791(15) 0.58420(12) 0.0409(3) Uani d . 1 . . N
    C1 0.2570(2) 0.68560(18) 0.57042(16) 0.0418(4) Uani d . 1 . . C
    C2 0.3021(3) 0.7581(2) 0.38177(18) 0.0561(5) Uani d . 1 . . C
    H2A 0.3519 0.7079 0.2978 0.067 Uiso calc R 1 . . H
    H2B 0.3761 0.8740 0.4261 0.067 Uiso calc R 1 . . H
    C3 0.0646(3) 0.7419(2) 0.35613(17) 0.0524(4) Uani d . 1 . . C
    H3A -0.0055 0.6284 0.2954 0.063 Uiso calc R 1 . . H
    H3B 0.0336 0.8121 0.3134 0.063 Uiso calc R 1 . . H
    C4 -0.0255(3) 0.78934(19) 0.48298(17) 0.0450(4) Uani d . 1 . . C
    C5 -0.0223(3) 0.7907(2) 0.70373(17) 0.0481(4) Uani d . 1 . . C
    H5A 0.0220 0.7255 0.7481 0.058 Uiso calc R 1 . . H
    H5B -0.1779 0.7556 0.6760 0.058 Uiso calc R 1 . . H
    C6 0.0371(3) 0.9712(2) 0.80199(15) 0.0455(4) Uani d . 1 . . C
    C7 -0.1168(3) 1.0423(2) 0.87086(18) 0.0579(5) Uani d . 1 . . C
    H7 -0.2566 0.9794 0.8536 0.070 Uiso calc R 1 . . H
    C8 -0.0646(4) 1.2056(3) 0.96491(19) 0.0713(6) Uani d . 1 . . C
    H8 -0.1678 1.2530 1.0109 0.086 Uiso calc R 1 . . H
    C9 0.1397(5) 1.2950(3) 0.98853(19) 0.0769(7) Uani d . 1 . . C
    C10 0.2970(4) 1.2313(3) 0.9237(2) 0.0785(7) Uani d . 1 . . C
    H10 0.4359 1.2959 0.9421 0.094 Uiso calc R 1 . . H
    C11 0.2438(3) 1.0669(2) 0.82924(19) 0.0619(5) Uani d . 1 . . C
    H11 0.3486 1.0210 0.7840 0.074 Uiso calc R 1 . . H
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    S1 0.0600(3) 0.0616(3) 0.0654(3) 0.0240(2) 0.0158(2) 0.0350(3)
    F1 0.1746(17) 0.0676(9) 0.0783(9) 0.0457(10) -0.0056(10) -0.0141(7)
    O1 0.0493(7) 0.0618(8) 0.0729(9) 0.0220(6) 0.0132(6) 0.0299(7)
    N1 0.0482(8) 0.0649(9) 0.0555(9) 0.0244(7) 0.0204(7) 0.0262(8)
    N2 0.0414(7) 0.0379(7) 0.0415(7) 0.0104(6) 0.0116(5) 0.0137(6)
    C1 0.0400(8) 0.0327(8) 0.0460(9) 0.0057(6) 0.0081(7) 0.0112(7)
    C2 0.0608(11) 0.0582(11) 0.0479(10) 0.0104(9) 0.0170(8) 0.0211(8)
    C3 0.0611(11) 0.0498(10) 0.0462(9) 0.0140(8) 0.0090(8) 0.0200(8)
    C4 0.0445(9) 0.0363(8) 0.0498(9) 0.0065(7) 0.0069(7) 0.0155(7)
    C5 0.0494(9) 0.0487(9) 0.0526(10) 0.0154(8) 0.0204(8) 0.0240(8)
    C6 0.0550(10) 0.0505(9) 0.0380(8) 0.0222(8) 0.0125(7) 0.0210(7)
    C7 0.0721(12) 0.0684(12) 0.0506(10) 0.0372(10) 0.0251(9) 0.0314(9)
    C8 0.1028(18) 0.0782(14) 0.0481(11) 0.0564(14) 0.0281(11) 0.0249(10)
    C9 0.118(2) 0.0578(12) 0.0427(11) 0.0394(14) 0.0011(11) 0.0047(9)
    C10 0.0777(15) 0.0582(12) 0.0725(14) 0.0112(11) -0.0068(11) 0.0070(11)
    C11 0.0600(12) 0.0548(11) 0.0588(11) 0.0186(9) 0.0097(9) 0.0103(9)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 . 1.6845(18) Yes
    F1 C9 . 1.369(2) Yes
    O1 C4 . 1.214(2) Yes
    N1 C1 . 1.322(2) Yes
    N1 C2 . 1.462(2) Yes
    N1 H1A . 0.9019 Yes
    N2 C1 . 1.401(2) Yes
    N2 C4 . 1.404(2) Yes
    N2 C5 . 1.474(2) Yes
    C2 C3 . 1.489(3) Yes
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C3 C4 . 1.498(2) Yes
    C3 H3A . 0.9700 ?
    C3 H3B . 0.9700 ?
    C5 C6 . 1.512(2) Yes
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 C11 . 1.382(3) Yes
    C6 C7 . 1.389(2) Yes
    C7 C8 . 1.384(3) Yes
    C7 H7 . 0.9300 ?
    C8 C9 . 1.353(4) Yes
    C8 H8 . 0.9300 ?
    C9 C10 . 1.365(3) Yes
    C10 C11 . 1.392(3) Yes
    C10 H10 . 0.9300 ?
    C11 H11 . 0.9300 Yes
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
    C1 N1 C2 . . 124.24(15) Yes
    C1 N1 H1A . . 113.0 ?
    C2 N1 H1A . . 121.5 ?
    C1 N2 C4 . . 123.17(13) Yes
    C1 N2 C5 . . 120.42(14) Yes
    C4 N2 C5 . . 116.17(13) Yes
    N1 C1 N2 . . 116.14(15) Yes
    N1 C1 S1 . . 121.25(13) Yes
    N2 C1 S1 . . 122.60(12) Yes
    N1 C2 C3 . . 108.63(14) Yes
    N1 C2 H2A . . 110.0 ?
    C3 C2 H2A . . 110.0 ?
    N1 C2 H2B . . 110.0 ?
    C3 C2 H2B . . 110.0 ?
    H2A C2 H2B . . 108.3 ?
    C2 C3 C4 . . 111.68(15) Yes
    C2 C3 H3A . . 109.3 ?
    C4 C3 H3A . . 109.3 ?
    C2 C3 H3B . . 109.3 ?
    C4 C3 H3B . . 109.3 ?
    H3A C3 H3B . . 107.9 ?
    O1 C4 N2 . . 119.87(16) Yes
    O1 C4 C3 . . 123.63(16) Yes
    N2 C4 C3 . . 116.46(15) Yes
    N2 C5 C6 . . 112.80(13) Yes
    N2 C5 H5A . . 109.0 ?
    C6 C5 H5A . . 109.0 ?
    N2 C5 H5B . . 109.0 ?
    C6 C5 H5B . . 109.0 ?
    H5A C5 H5B . . 107.8 ?
    C11 C6 C7 . . 118.62(17) Yes
    C11 C6 C5 . . 121.74(15) Yes
    C7 C6 C5 . . 119.60(17) Yes
    C8 C7 C6 . . 120.8(2) Yes
    C8 C7 H7 . . 119.6 ?
    C6 C7 H7 . . 119.6 ?
    C9 C8 C7 . . 118.70(19) Yes
    C9 C8 H8 . . 120.7 ?
    C7 C8 H8 . . 120.7 ?
    C8 C9 C10 . . 122.9(2) Yes
    C8 C9 F1 . . 119.0(2) Yes
    C10 C9 F1 . . 118.1(3) Yes
    C9 C10 C11 . . 118.2(2) Yes
    C9 C10 H10 . . 120.9 ?
    C11 C10 H10 . . 120.9 ?
    C6 C11 C10 . . 120.79(19) Yes
    C6 C11 H11 . . 119.6 ?
    C10 C11 H11 . . 119.6 ?
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
    C2 N1 C1 N2 . . . . 11.0(2) Yes
    C2 N1 C1 S1 . . . . -168.01(13) Yes
    C4 N2 C1 N1 . . . . 12.1(2) Yes
    C5 N2 C1 N1 . . . . -173.80(14) Yes
    C4 N2 C1 S1 . . . . -168.94(11) Yes
    C5 N2 C1 S1 . . . . 5.2(2) Yes
    C1 N1 C2 C3 . . . . -42.1(2) Yes
    N1 C2 C3 C4 . . . . 49.2(2) Yes
    C1 N2 C4 O1 . . . . 177.61(14) Yes
    C5 N2 C4 O1 . . . . 3.2(2) Yes
    C1 N2 C4 C3 . . . . -0.3(2) Yes
    C5 N2 C4 C3 . . . . -174.63(14) Yes
    C2 C3 C4 O1 . . . . 150.56(17) Yes
    C2 C3 C4 N2 . . . . -31.7(2) Yes
    C1 N2 C5 C6 . . . . 103.52(17) Yes
    C4 N2 C5 C6 . . . . -81.95(17) Yes
    N2 C5 C6 C11 . . . . -39.9(2) Yes
    N2 C5 C6 C7 . . . . 142.47(15) Yes
    C11 C6 C7 C8 . . . . 0.0(3) Yes
    C5 C6 C7 C8 . . . . 177.67(16) Yes
    C6 C7 C8 C9 . . . . 0.0(3) Yes
    C7 C8 C9 C10 . . . . 0.0(3) Yes
    C7 C8 C9 F1 . . . . 179.54(17) Yes
    C8 C9 C10 C11 . . . . 0.0(4) Yes
    F1 C9 C10 C11 . . . . -179.59(19) Yes
    C7 C6 C11 C10 . . . . 0.0(3) Yes
    C5 C6 C11 C10 . . . . -177.66(18) Yes
    C9 C10 C11 C6 . . . . 0.1(3) Yes
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 H1A S1 2_666 0.90 2.71 3.4905(18) 146
    N1 H1A O1 1_655 0.90 2.59 3.035(2) 111
