#------------------------------------------------------------------------------
#$Date: 2018-09-26 06:29:44 +0300 (Wed, 26 Sep 2018) $
#$Revision: 211175 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/30/8103079.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8103079
loop_
_publ_author_name
'Yi-Feng Zhu'
'Mei-Rong Li'
'Xiao-Qing Cai'
'Mao-Lin Hu'
_publ_section_title
;
 Crystal structure of
 5-fluoro-3-(thiophene-2-carbonyl)pyrimidine-2,4(1H,3H)-dione, C9H5FN2O3S
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              107
_journal_volume                  226
_journal_year                    2011
_chemical_formula_moiety         'C9 H5 F N2 O3 S'
_chemical_formula_sum            'C9 H5 F N2 O3 S'
_chemical_formula_weight         240.21
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.490(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.574(4)
_cell_length_b                   19.770(15)
_cell_length_c                   8.866(7)
_cell_measurement_reflns_used    1792
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.893
_cell_measurement_theta_min      2.548
_cell_volume                     960.7(13)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL(Bruker, 2002)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scan'
_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  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0466
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4890
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.06
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.344
_exptl_absorpt_correction_T_max  0.9534
_exptl_absorpt_correction_T_min  0.8803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1696
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0519
_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)+(0.0558P)²+0.4425P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1225
_refine_ls_wR_factor_ref         0.1275
_reflns_number_gt                1501
_reflns_number_total             1696
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            1267-3261.cff
_cod_data_source_block           2141m
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8103079
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.12838(15) 0.74958(3) 0.33761(10) 0.0567(3) Uani 1 1 d .
F1 F -0.0868(4) 0.39426(9) 0.3615(2) 0.0771(7) Uani 1 1 d .
O1 O -0.1472(4) 0.64303(10) 0.1304(2) 0.0562(6) Uani 1 1 d .
O2 O 0.3464(3) 0.57222(9) 0.0491(2) 0.0459(5) Uani 1 1 d .
O3 O -0.1932(4) 0.52991(11) 0.3635(2) 0.0563(6) Uani 1 1 d .
N1 N 0.0964(4) 0.55159(9) 0.2187(2) 0.0330(5) Uani 1 1 d .
N2 N 0.3082(4) 0.46456(10) 0.1294(2) 0.0384(5) Uani 1 1 d .
H2A H 0.4152 0.4502 0.0783 0.046 Uiso 1 1 calc R
C1 C 0.3954(6) 0.76345(16) 0.4590(4) 0.0588(8) Uani 1 1 d .
H1 H 0.4401 0.8051 0.5041 0.071 Uiso 1 1 calc R
C2 C 0.5366(6) 0.70767(15) 0.4836(3) 0.0543(8) Uani 1 1 d .
H2 H 0.6899 0.7067 0.5461 0.065 Uiso 1 1 calc R
C3 C 0.4241(5) 0.65110(14) 0.4034(3) 0.0446(6) Uani 1 1 d .
H3 H 0.4943 0.6083 0.4079 0.054 Uiso 1 1 calc R
C4 C 0.1996(4) 0.66618(12) 0.3180(3) 0.0353(6) Uani 1 1 d .
C5 C 0.0328(4) 0.62452(12) 0.2153(3) 0.0354(6) Uani 1 1 d .
C6 C 0.2586(4) 0.53157(12) 0.1274(3) 0.0340(6) Uani 1 1 d .
C7 C 0.1971(5) 0.41873(13) 0.2083(3) 0.0430(6) Uani 1 1 d .
H7 H 0.2373 0.3731 0.2059 0.052 Uiso 1 1 calc R
C8 C 0.0326(5) 0.43893(13) 0.2881(3) 0.0447(7) Uani 1 1 d .
C9 C -0.0375(5) 0.50842(13) 0.2977(3) 0.0396(6) Uani 1 1 d .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 S1 C4 91.56(14)
C6 N1 C9 125.8(2)
C6 N1 C5 116.61(19)
C9 N1 C5 116.99(19)
C6 N2 C7 123.3(2)
C6 N2 H2A 118.4
C7 N2 H2A 118.4
C2 C1 S1 113.0(2)
C2 C1 H1 123.5
S1 C1 H1 123.5
C1 C2 C3 112.0(3)
C1 C2 H2 124.0
C3 C2 H2 124.0
C4 C3 C2 112.5(3)
C4 C3 H3 123.7
C2 C3 H3 123.7
C3 C4 C5 130.2(2)
C3 C4 S1 110.99(19)
C5 C4 S1 118.76(18)
O1 C5 C4 126.5(2)
O1 C5 N1 118.7(2)
C4 C5 N1 114.8(2)
O2 C6 N2 123.4(2)
O2 C6 N1 121.2(2)
N2 C6 N1 115.3(2)
C8 C7 N2 120.0(2)
C8 C7 H7 120.0
N2 C7 H7 120.0
C7 C8 F1 121.0(3)
C7 C8 C9 123.0(2)
F1 C8 C9 115.9(2)
O3 C9 N1 121.5(2)
O3 C9 C8 126.3(2)
N1 C9 C8 112.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.693(4)
S1 C4 1.712(3)
F1 C8 1.343(3)
O1 C5 1.197(3)
O2 C6 1.221(3)
O3 C9 1.208(3)
N1 C6 1.377(3)
N1 C9 1.403(3)
N1 C5 1.484(3)
N2 C6 1.353(3)
N2 C7 1.360(3)
N2 H2A 0.8600
C1 C2 1.349(4)
C1 H1 0.9300
C2 C3 1.410(4)
C2 H2 0.9300
C3 C4 1.372(4)
C3 H3 0.9300
C4 C5 1.436(4)
C7 C8 1.318(4)
C7 H7 0.9300
C8 C9 1.435(4)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O2 0.86 1.95 2.802(3) 173.4 3_665
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
C4 S1 C1 C2 0.7(3)
S1 C1 C2 C3 -0.9(4)
C1 C2 C3 C4 0.7(4)
C2 C3 C4 C5 176.6(3)
C2 C3 C4 S1 -0.2(3)
C1 S1 C4 C3 -0.3(2)
C1 S1 C4 C5 -177.5(2)
C3 C4 C5 O1 -170.3(3)
S1 C4 C5 O1 6.3(4)
C3 C4 C5 N1 9.7(4)
S1 C4 C5 N1 -173.66(16)
C6 N1 C5 O1 94.9(3)
C9 N1 C5 O1 -76.8(3)
C6 N1 C5 C4 -85.1(3)
C9 N1 C5 C4 103.2(3)
C7 N2 C6 O2 -175.2(2)
C7 N2 C6 N1 3.7(4)
C9 N1 C6 O2 171.6(2)
C5 N1 C6 O2 0.7(3)
C9 N1 C6 N2 -7.4(3)
C5 N1 C6 N2 -178.3(2)
C6 N2 C7 C8 -0.1(4)
N2 C7 C8 F1 177.1(2)
N2 C7 C8 C9 -0.3(4)
C6 N1 C9 O3 -172.8(2)
C5 N1 C9 O3 -1.9(3)
C6 N1 C9 C8 6.7(3)
C5 N1 C9 C8 177.6(2)
C7 C8 C9 O3 176.9(3)
F1 C8 C9 O3 -0.7(4)
C7 C8 C9 N1 -2.6(4)
F1 C8 C9 N1 179.7(2)
