#------------------------------------------------------------------------------
#$Date: 2025-08-23 01:35:05 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301870 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/03/7240383.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_7240383
loop_
_publ_author_name
'Dai, Xia-Lin'
'Wu, Chao'
'Li, Jin-Hui'
'Liu, Lian-Chao'
'He, Xin'
'Lu, Tong-Bu'
'Chen, Jia-Mei'
_publ_section_title
;
 Modulating the solubility and pharmacokinetic property of 5-fluorouracil
 via cocrystals
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00409J
_journal_year                    2020
_chemical_formula_moiety         'C4 H3 F N2 O2, C7 H6 O4'
_chemical_formula_sum            'C11 H9 F N2 O6'
_chemical_formula_weight         284.20
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-12-09 deposited with the CCDC.	2020-04-23 downloaded from the CCDC.
;
_cell_angle_alpha                111.550(7)
_cell_angle_beta                 107.076(7)
_cell_angle_gamma                100.662(6)
_cell_formula_units_Z            2
_cell_length_a                   7.8352(6)
_cell_length_b                   8.9191(7)
_cell_length_c                   9.4663(7)
_cell_measurement_reflns_used    3598
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      78.5570
_cell_measurement_theta_min      5.4680
_cell_volume                     555.34(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  68.00   0.50    0.50    --    0.00  57.00-150.00  192
  2  ω    -29.00  41.00   0.50    0.50    --    0.00  37.00   0.00  140
  3  ω     51.00  85.00   0.50    0.50    --    0.00  37.00   0.00   68
  4  ω    -27.00  10.00   0.50    0.50    --    0.00  57.00 120.00   74
  5  ω     75.00 113.00   0.50    0.50    --  106.20 -82.00 150.00   76
  6  ω     95.00 124.00   0.50    0.50    --  106.20  61.00-150.00   58
  7  ω     96.00 141.00   0.50    0.50    --  106.20  45.00-180.00   90
  8  ω     20.00  68.00   0.50    0.50    --  106.20 -45.00-120.00   96
  9  ω    106.00 132.00   0.50    0.50    --  106.20 -77.00 -90.00   52
 10  ω     33.00  73.00   0.50    0.50    --  106.20 -82.00 -30.00   80
 11  ω     82.00 148.00   0.50    0.50    --  106.20  45.00-150.00  132
 12  ω     80.00 179.00   0.50    0.50    --  106.20  45.00 150.00  198
 13  ω     38.00 137.00   0.50    0.50    --  106.20 -82.00  60.00  198
 14  ω    122.00 196.00   0.50    0.50    --  106.20  45.00  60.00  148
 15  ω     37.00  70.00   0.50    0.50    --  106.20 -82.00-120.00   66
 16  ω     17.00  91.00   0.50    0.50    --  106.20 -77.00 -90.00  148
 17  ω     86.00 162.00   0.50    0.50    --  106.20  45.00 120.00  152
 18  ω     78.00 132.00   0.50    0.50    --  106.20 -82.00-120.00  108
 19  ω    171.00 196.00   0.50    0.50    --  106.20  61.00-150.00   50
 20  ω     78.00 134.00   0.50    0.50    --  106.20 -45.00-120.00  112
 21  ω    150.00 192.00   0.50    0.50    --  106.20  45.00-180.00   84
 22  ω     90.00 130.00   0.50    0.50    --  106.20 -82.00 -30.00   80
 23  ω     96.00 141.00   0.50    0.50    --  106.20 -77.00  30.00   90
 24  ω    153.00 191.00   0.50    0.50    --  106.20  45.00-150.00   76
 25  ω     28.00  54.00   0.50    0.50    --  106.20 -77.00  30.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0968933000
_diffrn_orient_matrix_UB_12      0.0298948000
_diffrn_orient_matrix_UB_13      0.1231715000
_diffrn_orient_matrix_UB_21      0.1941652000
_diffrn_orient_matrix_UB_22      0.0696631000
_diffrn_orient_matrix_UB_23      0.1443483000
_diffrn_orient_matrix_UB_31      0.0192005000
_diffrn_orient_matrix_UB_32      0.1814906000
_diffrn_orient_matrix_UB_33      0.0169744000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_av_unetI/netI     0.0659
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5446
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.650
_diffrn_reflns_theta_min         5.471
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.319
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.924
_refine_diff_density_rms         0.205
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2323
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0900
_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)+(0.1971P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2227
_refine_ls_wR_factor_ref         0.2295
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2062
_reflns_number_total             2323
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00409j2.cif
_cod_data_source_block           5FU-35DHBA
_cod_original_cell_volume        555.34(8)
_cod_database_code               7240383
_shelx_shelxl_version_number     2016/6
_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.
;
_reflns_odcompleteness_completeness 99.16
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C6(H6A), C8(H8), C10(H10), C4(H4A)
2.b Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4), O6(H6)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.602
_oxdiff_exptl_absorpt_empirical_full_min 0.485
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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 1.52919(16) 0.68257(15) 1.05494(16) 0.0288(4) Uani 1 1 d . . . . .
O1 O 0.86132(19) 0.78382(16) 0.89178(17) 0.0188(4) Uani 1 1 d . . . . .
O5 O 0.65290(18) 0.35891(16) 0.67333(18) 0.0203(4) Uani 1 1 d . . . . .
O3 O 0.09392(17) -0.19078(15) 0.28027(17) 0.0196(4) Uani 1 1 d . . . . .
H3 H 0.187445 -0.210041 0.326680 0.029 Uiso 1 1 calc GR . . . .
O4 O -0.16717(19) 0.26089(16) 0.37666(19) 0.0235(4) Uani 1 1 d . . . . .
H4 H -0.265024 0.179950 0.315038 0.035 Uiso 1 1 calc GR . . . .
O6 O 0.51615(18) 0.55957(16) 0.69095(17) 0.0213(4) Uani 1 1 d . . . . .
H6 H 0.621661 0.621563 0.761935 0.032 Uiso 1 1 calc GR . . . .
O2 O 1.49972(19) 1.00509(17) 1.16599(18) 0.0273(4) Uani 1 1 d . . . . .
N2 N 1.0296(2) 0.60022(19) 0.8698(2) 0.0172(4) Uani 1 1 d . . . . .
H2 H 0.927903 0.513883 0.807327 0.021 Uiso 1 1 calc R . . . .
N1 N 1.1822(2) 0.89146(18) 1.01691(19) 0.0163(4) Uani 1 1 d . . . . .
H1 H 1.175854 0.992817 1.043789 0.020 Uiso 1 1 calc R . . . .
C9 C -0.0180(2) 0.2030(2) 0.3989(2) 0.0154(4) Uani 1 1 d . . . . .
C1 C 1.0152(3) 0.7585(2) 0.9239(2) 0.0149(4) Uani 1 1 d . . . . .
C6 C 0.2999(2) 0.1003(2) 0.4544(2) 0.0161(4) Uani 1 1 d . . . . .
H6A H 0.406215 0.066035 0.472238 0.019 Uiso 1 1 calc R . . . .
C8 C -0.0386(2) 0.0308(2) 0.3249(2) 0.0151(4) Uani 1 1 d . . . . .
H8 H -0.157624 -0.050308 0.256128 0.018 Uiso 1 1 calc R . . . .
C5 C 0.3183(2) 0.27352(19) 0.5278(2) 0.0139(4) Uani 1 1 d . . . . .
C7 C 0.1219(2) -0.0189(2) 0.3551(2) 0.0148(4) Uani 1 1 d . . . . .
C11 C 0.5106(2) 0.3991(2) 0.6357(2) 0.0148(4) Uani 1 1 d . . . . .
C10 C 0.1610(3) 0.3265(2) 0.5006(2) 0.0157(4) Uani 1 1 d . . . . .
H10 H 0.174159 0.441850 0.548843 0.019 Uiso 1 1 calc R . . . .
C2 C 1.3605(2) 0.8778(2) 1.0717(2) 0.0176(4) Uani 1 1 d . . . . .
C3 C 1.3603(3) 0.7052(2) 1.0087(2) 0.0190(4) Uani 1 1 d . . . . .
C4 C 1.1998(3) 0.5713(2) 0.9103(2) 0.0196(4) Uani 1 1 d . . . . .
H4A H 1.203974 0.460505 0.870234 0.023 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 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_publ_flag
C7 O3 H3 109.5 . . ?
C9 O4 H4 109.5 . . ?
C11 O6 H6 109.5 . . ?
C1 N2 H2 118.5 . . ?
C1 N2 C4 122.92(16) . . ?
C4 N2 H2 118.5 . . ?
C1 N1 H1 117.0 . . ?
C1 N1 C2 126.05(15) . . ?
C2 N1 H1 117.0 . . ?
O4 C9 C8 122.50(16) . . ?
O4 C9 C10 116.54(15) . . ?
C8 C9 C10 120.96(16) . . ?
O1 C1 N2 122.73(16) . . ?
O1 C1 N1 121.29(16) . . ?
N2 C1 N1 115.98(15) . . ?
C5 C6 H6A 120.4 . . ?
C7 C6 H6A 120.4 . . ?
C7 C6 C5 119.10(15) . . ?
C9 C8 H8 120.5 . . ?
C9 C8 C7 119.07(17) . . ?
C7 C8 H8 120.5 . . ?
C6 C5 C11 118.17(14) . . ?
C10 C5 C6 121.02(16) . . ?
C10 C5 C11 120.81(14) . . ?
O3 C7 C6 122.06(14) . . ?
O3 C7 C8 116.83(16) . . ?
C6 C7 C8 121.11(16) . . ?
O5 C11 O6 122.31(16) . . ?
O5 C11 C5 123.58(14) . . ?
O6 C11 C5 114.10(13) . . ?
C9 C10 H10 120.6 . . ?
C5 C10 C9 118.72(15) . . ?
C5 C10 H10 120.6 . . ?
O2 C2 N1 120.86(16) . . ?
O2 C2 C3 125.80(16) . . ?
N1 C2 C3 113.33(16) . . ?
F1 C3 C2 116.52(16) . . ?
F1 C3 C4 121.23(17) . . ?
C4 C3 C2 122.24(16) . . ?
N2 C4 H4A 120.4 . . ?
C3 C4 N2 119.22(17) . . ?
C3 C4 H4A 120.4 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C3 1.345(2) . ?
O1 C1 1.238(2) . ?
O5 C11 1.228(2) . ?
O3 H3 0.8200 . ?
O3 C7 1.3735(19) . ?
O4 H4 0.8200 . ?
O4 C9 1.3549(19) . ?
O6 H6 0.8200 . ?
O6 C11 1.318(2) . ?
O2 C2 1.225(2) . ?
N2 H2 0.8600 . ?
N2 C1 1.353(2) . ?
N2 C4 1.375(2) . ?
N1 H1 0.8600 . ?
N1 C1 1.370(2) . ?
N1 C2 1.385(2) . ?
C9 C8 1.388(2) . ?
C9 C10 1.401(2) . ?
C6 H6A 0.9300 . ?
C6 C5 1.400(2) . ?
C6 C7 1.381(2) . ?
C8 H8 0.9300 . ?
C8 C7 1.396(2) . ?
C5 C11 1.483(2) . ?
C5 C10 1.388(2) . ?
C10 H10 0.9300 . ?
C2 C3 1.431(3) . ?
C3 C4 1.347(3) . ?
C4 H4A 0.9300 . ?
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
O3 H3 O5 0.82 1.99 2.7294(18) 150.5 2_656
O4 H4 O2 0.82 1.90 2.7187(19) 175.1 1_344
O6 H6 O1 0.82 1.86 2.6673(19) 167.4 .
N2 H2 O5 0.86 2.04 2.879(2) 164.4 .
N1 H1 O1 0.86 1.96 2.820(2) 174.4 2_777
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
_geom_torsion_publ_flag
F1 C3 C4 N2 178.23(15) . . . . ?
O4 C9 C8 C7 -179.40(15) . . . . ?
O4 C9 C10 C5 179.70(15) . . . . ?
O2 C2 C3 F1 -1.6(3) . . . . ?
O2 C2 C3 C4 177.4(2) . . . . ?
N1 C2 C3 F1 179.03(15) . . . . ?
N1 C2 C3 C4 -2.1(3) . . . . ?
C9 C8 C7 O3 179.42(14) . . . . ?
C9 C8 C7 C6 -1.3(3) . . . . ?
C1 N2 C4 C3 0.3(3) . . . . ?
C1 N1 C2 O2 -173.84(17) . . . . ?
C1 N1 C2 C3 5.6(3) . . . . ?
C6 C5 C11 O5 -5.2(3) . . . . ?
C6 C5 C11 O6 175.82(15) . . . . ?
C6 C5 C10 C9 0.6(3) . . . . ?
C8 C9 C10 C5 -0.7(3) . . . . ?
C5 C6 C7 O3 -179.60(15) . . . . ?
C5 C6 C7 C8 1.1(3) . . . . ?
C7 C6 C5 C11 179.18(14) . . . . ?
C7 C6 C5 C10 -0.8(3) . . . . ?
C11 C5 C10 C9 -179.37(15) . . . . ?
C10 C9 C8 C7 1.1(3) . . . . ?
C10 C5 C11 O5 174.78(16) . . . . ?
C10 C5 C11 O6 -4.2(2) . . . . ?
C2 N1 C1 O1 174.19(17) . . . . ?
C2 N1 C1 N2 -6.0(3) . . . . ?
C2 C3 C4 N2 -0.6(3) . . . . ?
C4 N2 C1 O1 -177.47(16) . . . . ?
C4 N2 C1 N1 2.8(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168341272
