# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1993395'
loop_
_audit_author_name
_audit_author_address
'Yan-Tuan Li'
;School of Medicine and Pharmacy, Ocean University of China
China
;
_audit_update_record             
;
2020-03-29 deposited with the CCDC.	2020-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        
'5-Fluoropyrimidine-2,4(1H,3H)-dione 3-(3,4-dihydroxyphenyl)acrylic acid'
_chemical_name_common            '5-Fluorouracil Caffeic Acid'
_chemical_melting_point          492
_chemical_formula_moiety         'C4 H3 F N2 O2?C9 H8 O4?2(H2 O)'
_chemical_formula_sum            'C13 H15 F N2 O8'
_chemical_formula_weight         346.27

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9299(11)
_cell_length_b                   6.9584(10)
_cell_length_c                   15.946(2)
_cell_angle_alpha                99.753(5)
_cell_angle_beta                 96.384(5)
_cell_angle_gamma                98.812(5)
_cell_volume                     741.43(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3336
_cell_measurement_theta_min      3.004
_cell_measurement_theta_max      25.834

_exptl_crystal_description       column
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.379
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.027
_exptl_absorpt_coefficient_mu    0.137
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15477
_diffrn_reflns_av_unetI/netI     0.0888
_diffrn_reflns_av_R_equivalents  0.0756
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.005
_diffrn_reflns_theta_max         27.604
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3419
_reflns_number_gt                1810
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0475P)²+0.6516P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3419
_refine_ls_number_parameters     244
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1550
_refine_ls_R_factor_gt           0.0688
_refine_ls_wR_factor_ref         0.1582
_refine_ls_wR_factor_gt          0.1339
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.5823(3) 1.4437(2) 0.76052(12) 0.0517(6) Uani 1 1 d . . . . .
O1 O 0.2666(3) 0.6774(3) 0.69975(13) 0.0466(6) Uani 1 1 d . . . . .
O2 O 0.4677(4) 1.2559(3) 0.88862(14) 0.0484(6) Uani 1 1 d . . . . .
N1 N 0.3652(4) 0.9690(4) 0.79277(16) 0.0363(7) Uani 1 1 d . . . . .
H1 H 0.326(5) 0.906(5) 0.833(2) 0.044 Uiso 1 1 d . U . . .
N2 N 0.3930(4) 0.9492(4) 0.64918(17) 0.0349(6) Uani 1 1 d . . . . .
H2A H 0.379(4) 0.879(3) 0.590(2) 0.042 Uiso 1 1 d D U . . .
C1 C 0.3386(4) 0.8558(4) 0.7120(2) 0.0322(7) Uani 1 1 d D . . . .
C2 C 0.4761(4) 1.1475(4) 0.66369(19) 0.0327(7) Uani 1 1 d D . . . .
H2 H 0.513250 1.207164 0.618627 0.039 Uiso 1 1 calc R U . . .
C3 C 0.5016(4) 1.2509(4) 0.74303(19) 0.0314(7) Uani 1 1 d . . . . .
C4 C 0.4457(4) 1.1659(4) 0.8143(2) 0.0343(7) Uani 1 1 d . . . . .
O3 O 0.2104(4) 0.4294(3) 0.55225(14) 0.0477(6) Uani 1 1 d D . . . .
H3 H 0.232(6) 0.511(5) 0.6003(16) 0.072 Uiso 1 1 d D U . . .
O4 O 0.3215(4) 0.6812(3) 0.49177(14) 0.0525(7) Uani 1 1 d . . . . .
O5 O 0.1466(4) -0.0165(3) 0.07973(14) 0.0538(7) Uani 1 1 d . . . . .
H5 H 0.200(6) 0.109(6) 0.084(3) 0.081 Uiso 1 1 d . U . . .
O6 O -0.0160(4) -0.3789(3) 0.08243(15) 0.0526(7) Uani 1 1 d D . . . .
H6A H -0.067(6) -0.487(4) 0.094(3) 0.079 Uiso 1 1 d D U . . .
C5 C 0.2540(5) 0.5071(5) 0.48495(19) 0.0367(8) Uani 1 1 d . . . . .
C6 C 0.2173(5) 0.3691(5) 0.4030(2) 0.0447(9) Uani 1 1 d . . . . .
H6 H 0.244994 0.420236 0.354606 0.054 Uiso 1 1 calc R U . . .
C7 C 0.1492(4) 0.1808(5) 0.3919(2) 0.0365(8) Uani 1 1 d . . . . .
H7 H 0.122908 0.131844 0.440974 0.044 Uiso 1 1 calc R U . . .
C8 C 0.1085(4) 0.0345(4) 0.30998(18) 0.0291(7) Uani 1 1 d . . . . .
C9 C 0.1472(4) 0.0843(4) 0.23188(19) 0.0327(7) Uani 1 1 d . . . . .
H9 H 0.200755 0.214309 0.230174 0.039 Uiso 1 1 calc R U . . .
C10 C 0.1078(4) -0.0546(4) 0.15746(19) 0.0329(7) Uani 1 1 d . . . . .
C11 C 0.0233(5) -0.2505(4) 0.15929(19) 0.0345(8) Uani 1 1 d . . . . .
C12 C -0.0152(4) -0.3009(4) 0.2358(2) 0.0359(8) Uani 1 1 d . . . . .
H12 H -0.070453 -0.430599 0.237326 0.043 Uiso 1 1 calc R U . . .
C13 C 0.0276(4) -0.1605(4) 0.31103(19) 0.0340(8) Uani 1 1 d . . . . .
H13 H 0.002003 -0.196877 0.362723 0.041 Uiso 1 1 calc R U . . .
O7 O 0.7518(4) 0.2505(4) 0.07193(16) 0.0598(8) Uani 1 1 d D . . . .
H7A H 0.786(6) 0.196(6) 0.0263(18) 0.090 Uiso 1 1 d D U . . .
H7B H 0.632(3) 0.259(7) 0.060(3) 0.090 Uiso 1 1 d D U . . .
O8 O 0.3492(5) 0.3270(4) 0.05902(16) 0.0721(9) Uani 1 1 d D . . . .
H8A H 0.371(7) 0.439(4) 0.091(3) 0.108 Uiso 1 1 d D U . . .
H8B H 0.294(7) 0.330(7) 0.0096(18) 0.108 Uiso 1 1 d D U . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C3 1.342(3) . ?
O1 C1 1.239(3) . ?
O2 C4 1.224(4) . ?
N1 C4 1.367(4) . ?
N1 C1 1.368(4) . ?
N1 H1 0.89(3) . ?
N2 C1 1.342(4) . ?
N2 C2 1.381(4) . ?
N2 H2A 0.97(3) . ?
C2 C3 1.324(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.431(4) . ?
O3 C5 1.324(4) . ?
O3 H3 0.857(18) . ?
O4 C5 1.212(4) . ?
O5 C10 1.358(4) . ?
O5 H5 0.88(4) . ?
O6 C11 1.362(4) . ?
O6 H6A 0.843(19) . ?
C5 C6 1.456(4) . ?
C6 C7 1.298(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.484(4) . ?
C7 H7 0.9300 . ?
C8 C13 1.390(4) . ?
C8 C9 1.391(4) . ?
C9 C10 1.370(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.405(4) . ?
C11 C12 1.369(4) . ?
C12 C13 1.384(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
O7 H7A 0.837(19) . ?
O7 H7B 0.846(19) . ?
O8 H8A 0.840(19) . ?
O8 H8B 0.842(19) . ?

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
C4 N1 C1 125.6(3) . . ?
C4 N1 H1 119(2) . . ?
C1 N1 H1 115(2) . . ?
C1 N2 C2 123.0(3) . . ?
C1 N2 H2A 121.1(6) . . ?
C2 N2 H2A 115.9(6) . . ?
O1 C1 N2 123.4(3) . . ?
O1 C1 N1 120.3(3) . . ?
N2 C1 N1 116.3(3) . . ?
C3 C2 N2 118.7(3) . . ?
C3 C2 H2 120.7 . . ?
N2 C2 H2 120.7 . . ?
C2 C3 F1 121.0(3) . . ?
C2 C3 C4 122.7(3) . . ?
F1 C3 C4 116.3(3) . . ?
O2 C4 N1 121.5(3) . . ?
O2 C4 C3 124.8(3) . . ?
N1 C4 C3 113.8(3) . . ?
C5 O3 H3 115(3) . . ?
C10 O5 H5 111(3) . . ?
C11 O6 H6A 105(3) . . ?
O4 C5 O3 121.8(3) . . ?
O4 C5 C6 122.6(3) . . ?
O3 C5 C6 115.5(3) . . ?
C7 C6 C5 125.5(3) . . ?
C7 C6 H6 117.2 . . ?
C5 C6 H6 117.2 . . ?
C6 C7 C8 127.6(3) . . ?
C6 C7 H7 116.2 . . ?
C8 C7 H7 116.2 . . ?
C13 C8 C9 118.5(3) . . ?
C13 C8 C7 118.8(3) . . ?
C9 C8 C7 122.8(3) . . ?
C10 C9 C8 121.2(3) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
O5 C10 C9 124.0(3) . . ?
O5 C10 C11 116.3(3) . . ?
C9 C10 C11 119.7(3) . . ?
O6 C11 C12 124.2(3) . . ?
O6 C11 C10 116.3(3) . . ?
C12 C11 C10 119.5(3) . . ?
C11 C12 C13 120.5(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C8 120.6(3) . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?
H7A O7 H7B 106(4) . . ?
H8A O8 H8B 112(5) . . ?

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
C2 N2 C1 O1 -179.0(3) . . . . ?
C2 N2 C1 N1 1.5(4) . . . . ?
C4 N1 C1 O1 179.0(3) . . . . ?
C4 N1 C1 N2 -1.5(5) . . . . ?
C1 N2 C2 C3 -0.6(4) . . . . ?
N2 C2 C3 F1 179.7(3) . . . . ?
N2 C2 C3 C4 -0.4(5) . . . . ?
C1 N1 C4 O2 -178.6(3) . . . . ?
C1 N1 C4 C3 0.6(4) . . . . ?
C2 C3 C4 O2 179.6(3) . . . . ?
F1 C3 C4 O2 -0.5(5) . . . . ?
C2 C3 C4 N1 0.4(4) . . . . ?
F1 C3 C4 N1 -179.7(3) . . . . ?
O4 C5 C6 C7 178.5(3) . . . . ?
O3 C5 C6 C7 -0.8(5) . . . . ?
C5 C6 C7 C8 179.7(3) . . . . ?
C6 C7 C8 C13 -177.4(3) . . . . ?
C6 C7 C8 C9 2.4(5) . . . . ?
C13 C8 C9 C10 -0.3(4) . . . . ?
C7 C8 C9 C10 180.0(3) . . . . ?
C8 C9 C10 O5 -178.3(3) . . . . ?
C8 C9 C10 C11 1.3(5) . . . . ?
O5 C10 C11 O6 -2.0(4) . . . . ?
C9 C10 C11 O6 178.4(3) . . . . ?
O5 C10 C11 C12 178.3(3) . . . . ?
C9 C10 C11 C12 -1.3(5) . . . . ?
O6 C11 C12 C13 -179.3(3) . . . . ?
C10 C11 C12 C13 0.3(5) . . . . ?
C11 C12 C13 C8 0.6(5) . . . . ?
C9 C8 C13 C12 -0.7(4) . . . . ?
C7 C8 C13 C12 179.1(3) . . . . ?

_refine_diff_density_max         0.514
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.052


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol/water'
