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#$Date: 2023-04-20 11:22:04 +0300 (Thu, 20 Apr 2023) $
#$Revision: 282764 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/70/8107096.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_8107096
loop_
_publ_author_name
'Barakat, Assem'
'Ghabbour, Hazem A.'
'Al-Qahtani, Bandar M.'
'Ali, M.'
'Mohammed Al-Majid, Abdullah'
_publ_section_title
;
 Crystal structure of
 5-(3-fluorobenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione;
 C13H11FN2O3
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1059
_journal_page_last               1061
_journal_paper_doi               10.1515/ncrs-2016-0050
_journal_volume                  231
_journal_year                    2016
_chemical_formula_sum            'C13 H11 F N2 O3'
_chemical_formula_weight         262.24
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                75.546(3)
_cell_angle_beta                 78.183(3)
_cell_angle_gamma                77.540(3)
_cell_formula_units_Z            2
_cell_length_a                   5.7471(4)
_cell_length_b                   7.8734(6)
_cell_length_c                   13.3112(11)
_cell_measurement_reflns_used    9887
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.77
_cell_measurement_theta_min      2.71
_cell_volume                     562.22(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II D8 venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus micro tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_sigmaI/netI    0.0433
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23518
_diffrn_reflns_theta_full        33.82
_diffrn_reflns_theta_max         33.82
_diffrn_reflns_theta_min         2.71
_diffrn_standards_decay_%        .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.9601
_exptl_absorpt_correction_T_min  0.9315
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS_Bruker_2014
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.559
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         4489
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0444
_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/[σ²(Fo²)+(0.0681P)²+0.0934P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1234
_reflns_number_gt                3552
_reflns_number_total             4489
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2016-0050_suppl.cif
_cod_data_source_block           a_a
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               8107096
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 1.25061(16) -0.01299(11) 0.08422(7) 0.0211(2) Uani 0.867(3) 1 d P A 1
H12A H 0.852(4) -0.207(3) 0.3958(17) 0.025 Uiso 0.867(3) 1 d P A 1
F1X F 0.8400(10) -0.2781(7) 0.4028(4) 0.0246(14) Uani 0.133(3) 1 d P A 2
H10X H 1.184(15) -0.041(16) 0.100(6) 0.01(4) Uiso 0.133(3) 1 d PD A 2
O1 O 0.18139(12) 0.54996(9) 0.06849(6) 0.01682(15) Uani 1 1 d . . .
O2 O -0.48209(12) 0.53819(10) 0.31923(6) 0.01656(15) Uani 1 1 d . . .
O3 O 0.20608(14) 0.17946(12) 0.40635(6) 0.02563(19) Uani 1 1 d . . .
N1 N -0.15531(13) 0.53510(10) 0.19059(6) 0.01138(15) Uani 1 1 d . . .
N2 N -0.14103(14) 0.34690(11) 0.35961(6) 0.01311(15) Uani 1 1 d . . .
C1 C 0.08620(15) 0.47922(12) 0.15508(7) 0.01141(16) Uani 1 1 d . . .
C2 C -0.29741(16) 0.67607(12) 0.12109(8) 0.01436(17) Uani 1 1 d . . .
H2A H -0.2071 0.6943 0.0495 0.022 Uiso 1 1 calc R . .
H2B H -0.3289 0.7870 0.1462 0.022 Uiso 1 1 calc R . .
H2C H -0.4510 0.6409 0.1213 0.022 Uiso 1 1 calc R . .
C3 C -0.27256(16) 0.47660(12) 0.29153(7) 0.01136(16) Uani 1 1 d . . .
C4 C -0.26907(18) 0.28622(15) 0.46583(8) 0.0201(2) Uani 1 1 d . . .
H4A H -0.4362 0.2821 0.4621 0.030 Uiso 1 1 calc R . .
H4B H -0.2678 0.3690 0.5097 0.030 Uiso 1 1 calc R . .
H4C H -0.1885 0.1670 0.4966 0.030 Uiso 1 1 calc R . .
C5 C 0.10251(16) 0.27685(12) 0.33638(7) 0.01387(17) Uani 1 1 d . . .
C6 C 0.21866(15) 0.32973(12) 0.22677(7) 0.01113(16) Uani 1 1 d . . .
C7 C 0.44179(15) 0.26030(12) 0.18138(7) 0.01137(16) Uani 1 1 d . . .
H7A H 0.4780 0.3195 0.1100 0.014 Uiso 1 1 calc R . .
C8 C 0.64058(15) 0.11879(11) 0.21320(7) 0.01130(16) Uani 1 1 d . . .
C9 C 0.84981(15) 0.11337(12) 0.13674(7) 0.01249(16) Uani 1 1 d . A .
H9A H 0.8520 0.1955 0.0709 0.015 Uiso 1 1 calc R . .
C10 C 1.05187(16) -0.01224(12) 0.15823(8) 0.01427(17) Uani 1 1 d D . .
C11 C 1.05874(17) -0.13634(13) 0.25222(8) 0.01570(18) Uani 1 1 d . A .
H11A H 1.2005 -0.2206 0.2655 0.019 Uiso 1 1 calc R . .
C12 C 0.84976(18) -0.13268(13) 0.32642(8) 0.01747(19) Uani 1 1 d . . .
C13 C 0.64288(17) -0.00834(13) 0.30820(7) 0.01560(18) Uani 1 1 d . A .
H13A H 0.5024 -0.0093 0.3602 0.019 Uiso 1 1 calc R . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C10 F1 H10X 35(9) . .
C12 F1X H12A 39(2) . .
C1 N1 C3 124.50(8) . .
C1 N1 C2 119.06(7) . .
C3 N1 C2 116.26(7) . .
C3 N2 C5 125.12(8) . .
C3 N2 C4 116.59(7) . .
C5 N2 C4 118.24(8) . .
O1 C1 N1 120.36(8) . .
O1 C1 C6 122.85(8) . .
N1 C1 C6 116.79(8) . .
N1 C2 H2A 109.5 . .
N1 C2 H2B 109.5 . .
H2A C2 H2B 109.5 . .
N1 C2 H2C 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
O2 C3 N2 121.41(8) . .
O2 C3 N1 121.08(8) . .
N2 C3 N1 117.50(8) . .
N2 C4 H4A 109.5 . .
N2 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
N2 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
O3 C5 N2 119.18(8) . .
O3 C5 C6 124.39(8) . .
N2 C5 C6 116.42(8) . .
C7 C6 C5 127.41(8) . .
C7 C6 C1 114.16(8) . .
C5 C6 C1 118.41(8) . .
C6 C7 C8 136.96(8) . .
C6 C7 H7A 111.5 . .
C8 C7 H7A 111.5 . .
C13 C8 C9 118.36(8) . .
C13 C8 C7 127.70(8) . .
C9 C8 C7 113.94(8) . .
C10 C9 C8 119.47(8) . .
C10 C9 H9A 120.3 . .
C8 C9 H9A 120.3 . .
F1 C10 C9 118.24(9) . .
F1 C10 C11 118.85(8) . .
C9 C10 C11 122.90(9) . .
F1 C10 H10X 15(7) . .
C9 C10 H10X 120(7) . .
C11 C10 H10X 115(7) . .
C10 C11 C12 117.29(9) . .
C10 C11 H11A 121.4 . .
C12 C11 H11A 121.4 . .
F1X C12 C13 120.8(3) . .
F1X C12 C11 115.6(3) . .
C13 C12 C11 121.70(9) . .
F1X C12 H12A 21.7(13) . .
C13 C12 H12A 117.7(12) . .
C11 C12 H12A 120.1(12) . .
C12 C13 C8 120.24(9) . .
C12 C13 H13A 119.9 . .
C8 C13 H13A 119.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C10 1.3470(12) .
F1 H10X 0.47(9) .
F1X C12 1.331(5) .
F1X H12A 0.56(2) .
O1 C1 1.2210(11) .
O2 C3 1.2151(11) .
O3 C5 1.2179(11) .
N1 C1 1.3838(11) .
N1 C3 1.3878(12) .
N1 C2 1.4698(11) .
N2 C3 1.3860(12) .
N2 C5 1.3906(11) .
N2 C4 1.4687(12) .
C1 C6 1.4919(12) .
C2 H2A 0.9800 .
C2 H2B 0.9800 .
C2 H2C 0.9800 .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C5 C6 1.4715(13) .
C6 C7 1.3614(12) .
C7 C8 1.4627(12) .
C7 H7A 0.9500 .
C8 C13 1.4037(13) .
C8 C9 1.4078(12) .
C9 C10 1.3812(12) .
C9 H9A 0.9500 .
C10 C11 1.3837(14) .
C10 H10X 1.001(5) .
C11 C12 1.3901(14) .
C11 H11A 0.9500 .
C12 C13 1.3886(13) .
C12 H12A 0.96(2) .
C13 H13A 0.9500 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C3 N1 C1 O1 -172.75(8) . . . .
C2 N1 C1 O1 2.24(13) . . . .
C3 N1 C1 C6 7.93(13) . . . .
C2 N1 C1 C6 -177.08(8) . . . .
C5 N2 C3 O2 -176.09(9) . . . .
C4 N2 C3 O2 0.98(13) . . . .
C5 N2 C3 N1 3.28(13) . . . .
C4 N2 C3 N1 -179.66(8) . . . .
C1 N1 C3 O2 176.07(8) . . . .
C2 N1 C3 O2 0.96(13) . . . .
C1 N1 C3 N2 -3.30(13) . . . .
C2 N1 C3 N2 -178.42(8) . . . .
C3 N2 C5 O3 171.14(9) . . . .
C4 N2 C5 O3 -5.88(14) . . . .
C3 N2 C5 C6 -7.93(13) . . . .
C4 N2 C5 C6 175.05(8) . . . .
O3 C5 C6 C7 11.32(16) . . . .
N2 C5 C6 C7 -169.66(9) . . . .
O3 C5 C6 C1 -166.87(10) . . . .
N2 C5 C6 C1 12.15(12) . . . .
O1 C1 C6 C7 -9.96(13) . . . .
N1 C1 C6 C7 169.34(8) . . . .
O1 C1 C6 C5 168.46(9) . . . .
N1 C1 C6 C5 -12.24(12) . . . .
C5 C6 C7 C8 1.87(17) . . . .
C1 C6 C7 C8 -179.87(10) . . . .
C6 C7 C8 C13 7.31(18) . . . .
C6 C7 C8 C9 -173.35(10) . . . .
C13 C8 C9 C10 -1.86(13) . . . .
C7 C8 C9 C10 178.74(8) . . . .
C8 C9 C10 F1 -179.15(8) . . . .
C8 C9 C10 C11 0.68(14) . . . .
F1 C10 C11 C12 -179.45(9) . . . .
C9 C10 C11 C12 0.72(15) . . . .
C10 C11 C12 F1X 163.4(3) . . . .
C10 C11 C12 C13 -0.92(15) . . . .
F1X C12 C13 C8 -163.8(3) . . . .
C11 C12 C13 C8 -0.28(16) . . . .
C9 C8 C13 C12 1.67(14) . . . .
C7 C8 C13 C12 -179.01(9) . . . .
