#------------------------------------------------------------------------------
#$Date: 2019-11-07 21:52:03 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223636 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/17/7231793.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_7231793
loop_
_publ_author_name
'Enkelmann, Dennis D.'
'Handelmann, Jens'
'Schauerte, Carsten'
'Merz, Klaus'
_publ_section_title
;
 Co-crystallization and polymorphic behaviour of 5-fluorouracil
;
_journal_issue                   13
_journal_name_full               CrystEngComm
_journal_page_first              2130
_journal_paper_doi               10.1039/C8CE01692E
_journal_volume                  21
_journal_year                    2019
_chemical_formula_sum            'C6 H8 F N2 O5'
_chemical_formula_weight         207.14
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2018-09-20 deposited with the CCDC.
2018-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                92.228(18)
_cell_angle_beta                 94.392(9)
_cell_angle_gamma                110.98(3)
_cell_formula_units_Z            2
_cell_length_a                   5.443(9)
_cell_length_b                   5.845(9)
_cell_length_c                   14.47(2)
_cell_measurement_reflns_used    1998
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.505
_cell_measurement_theta_min      2.831
_cell_volume                     427.5(11)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_device_type  'Rigaku Mercury375R/M CCD (XtaLAB mini)'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0126
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            1998
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.505
_diffrn_reflns_theta_min         2.831
_exptl_absorpt_coefficient_mu    0.153
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_description       prism
_exptl_crystal_F_000             214
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         1805
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0521
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0962P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1386
_refine_ls_wR_factor_ref         0.1537
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1232
_reflns_number_total             1805
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce01692e2.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
'Adding full bibliography for 7231792--7231793.cif.'
_cod_database_code               7231793
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.970
_shelx_estimated_absorpt_t_max   0.985
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
F1 F 0.9437(3) 0.1476(3) 0.13545(9) 0.0619(5) Uani 1 1 d
O1 O 0.8220(3) 0.2078(3) 0.49785(11) 0.0515(5) Uani 1 1 d
N1 N 0.9888(4) 0.0668(3) 0.37838(13) 0.0398(5) Uani 1 1 d
O2 O 1.1553(3) -0.0879(3) 0.26331(11) 0.0536(5) Uani 1 1 d
O3 O 1.4739(4) -0.3814(3) 0.16723(11) 0.0563(5) Uani 1 1 d
O5 O 0.5509(4) 0.3910(4) 0.62711(15) 0.0585(5) Uani 1 1 d
N2 N 0.7542(4) 0.3197(3) 0.35166(12) 0.0430(5) Uani 1 1 d
C2 C 1.0297(4) 0.0398(4) 0.28734(15) 0.0393(5) Uani 1 1 d
O4 O 1.2396(4) -0.1949(4) 0.09156(13) 0.0664(6) Uani 1 1 d
C4 C 0.7830(5) 0.3032(4) 0.25924(16) 0.0453(5) Uani 1 1 d
C3 C 0.9141(4) 0.1696(4) 0.22643(14) 0.0428(5) Uani 1 1 d
C1 C 0.8524(4) 0.1999(4) 0.41507(15) 0.0392(5) Uani 1 1 d
C6 C 1.4323(7) -0.4094(6) 0.00014(17) 0.0563(7) Uani 1 1 d
C5 C 1.3883(5) -0.3310(4) 0.09492(15) 0.0441(5) Uani 1 1 d
H2 H 0.702(5) 0.391(4) 0.2204(18) 0.050(7) Uiso 1 1 d
H1 H 1.044(4) -0.012(4) 0.4171(16) 0.035(6) Uiso 1 1 d
H3 H 0.662(5) 0.425(5) 0.3728(17) 0.054(7) Uiso 1 1 d
H4 H 1.218(6) -0.161(5) 0.159(2) 0.073(9) Uiso 1 1 d
H7 H 0.585(8) 0.339(7) 0.669(3) 0.095(15) Uiso 1 1 d
H8 H 0.632(7) 0.330(6) 0.576(3) 0.102(12) Uiso 1 1 d
H5 H 1.510(8) -0.281(7) -0.033(3) 0.105(13) Uiso 1 1 d
H6 H 1.273(7) -0.467(6) -0.036(2) 0.089(11) Uiso 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'
F F 0.0171 0.0103 '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'
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
C2 N1 C1 127.23(18) .
C2 N1 H1 118.3(16) .
C1 N1 H1 114.3(16) .
H7 O5 H8 106(4) .
C4 N2 C1 122.80(19) .
C4 N2 H3 117.9(15) .
C1 N2 H3 119.3(15) .
O2 C2 N1 120.69(19) .
O2 C2 C3 125.5(2) .
N1 C2 C3 113.79(19) .
C5 O4 H4 104.3(16) .
C3 C4 N2 120.8(2) .
C3 C4 H2 123.1(15) .
N2 C4 H2 116.1(15) .
C4 C3 F1 122.24(19) .
C4 C3 C2 120.9(2) .
F1 C3 C2 116.82(19) .
O1 C1 N2 123.53(19) .
O1 C1 N1 122.08(19) .
N2 C1 N1 114.4(2) .
C6 C6 C5 113.8(3) 2_845
C6 C6 H5 112(2) 2_845
C5 C6 H5 112(2) .
C6 C6 H6 112(2) 2_845
C5 C6 H6 109(2) .
H5 C6 H6 96(3) .
O3 C5 O4 122.2(2) .
O3 C5 C6 125.9(2) .
O4 C5 C6 111.9(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C3 1.345(3) .
O1 C1 1.223(3) .
N1 C2 1.365(3) .
N1 C1 1.371(3) .
N1 H1 0.84(2) .
O2 C2 1.236(3) .
O3 C5 1.203(3) .
O5 H7 0.72(4) .
O5 H8 1.00(4) .
N2 C4 1.362(3) .
N2 C1 1.364(3) .
N2 H3 0.98(3) .
C2 C3 1.435(3) .
O4 C5 1.322(3) .
O4 H4 1.01(3) .
C4 C3 1.329(3) .
C4 H2 0.96(2) .
C6 C6 1.492(5) 2_845
C6 C5 1.493(4) .
C6 H5 0.90(4) .
C6 H6 0.92(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
_geom_torsion_site_symmetry_1
C1 N1 C2 O2 -179.4(2) .
C1 N1 C2 C3 0.3(3) .
C1 N2 C4 C3 -1.0(4) .
N2 C4 C3 F1 179.3(2) .
N2 C4 C3 C2 -0.2(4) .
O2 C2 C3 C4 -179.8(2) .
N1 C2 C3 C4 0.5(3) .
O2 C2 C3 F1 0.7(3) .
N1 C2 C3 F1 -179.02(18) .
C4 N2 C1 O1 -178.0(2) .
C4 N2 C1 N1 1.7(3) .
C2 N1 C1 O1 178.3(2) .
C2 N1 C1 N2 -1.4(3) .
C6 C6 C5 O3 7.8(5) 2_845
C6 C6 C5 O4 -172.2(4) 2_845
