# 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 1972188'
loop_
_audit_author_name
_audit_author_address
'Yan-Tuan Li'
;School of Medicine and Pharmacy, Ocean University of China 
China
;
_audit_update_record             
;
2019-12-16 deposited with the CCDC.	2020-06-29 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 2-ammonio-3-phenylpropanoate'
_chemical_name_common            '5-fluorouracil L-phenylalanine'
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H3 F N2 O2, C9 H11 N O2'
_chemical_formula_sum            'C13 H14 F N3 O4'
_chemical_formula_weight         295.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.00870(10)
_cell_length_b                   12.3981(2)
_cell_length_c                   15.1304(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1314.75(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2972
_cell_measurement_theta_min      4.5780
_cell_measurement_theta_max      72.9370

_exptl_crystal_description       column
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.038
_shelx_estimated_absorpt_T_min   0.746
_shelx_estimated_absorpt_T_max   0.950
_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      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4565
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.611
_diffrn_reflns_theta_max         73.244
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2555
_reflns_number_gt                2421
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.688
_reflns_Friedel_fraction_max     0.944
_reflns_Friedel_fraction_full    1.000

_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)+(0.0365P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 944 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.17(14)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         2555
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0775
_refine_ls_wR_factor_gt          0.0754
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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 0.4556(2) 0.85422(10) 0.44088(9) 0.0213(3) Uani 1 1 d . . . . .
O1 O 0.6243(2) 0.53722(13) 0.21368(10) 0.0147(4) Uani 1 1 d . . . . .
O2 O 0.5179(3) 0.64377(13) 0.49728(10) 0.0178(4) Uani 1 1 d . . . . .
N1 N 0.5613(3) 0.71533(15) 0.23835(13) 0.0126(4) Uani 1 1 d . . . . .
N2 N 0.5705(3) 0.59297(15) 0.35449(13) 0.0119(4) Uani 1 1 d . . . . .
C1 C 0.5879(3) 0.61164(17) 0.26498(15) 0.0113(4) Uani 1 1 d . . . . .
C2 C 0.5288(3) 0.66852(18) 0.41830(15) 0.0132(5) Uani 1 1 d . . . . .
C3 C 0.5002(3) 0.77525(17) 0.38266(15) 0.0141(5) Uani 1 1 d . . . . .
C4 C 0.5141(3) 0.79612(18) 0.29611(15) 0.0134(5) Uani 1 1 d . . . . .
O3 O 0.5850(3) 0.37977(12) 0.39812(11) 0.0158(4) Uani 1 1 d . . . . .
O4 O 0.4124(2) 0.24078(13) 0.44646(11) 0.0169(4) Uani 1 1 d . . . . .
N3 N 0.6860(3) 0.44633(15) 0.55662(13) 0.0115(4) Uani 1 1 d . . . . .
C5 C 0.5082(3) 0.32529(17) 0.45818(15) 0.0120(4) Uani 1 1 d . . . . .
C6 C 0.5342(3) 0.36196(17) 0.55414(15) 0.0111(4) Uani 1 1 d . . . . .
C7 C 0.3508(3) 0.4040(2) 0.59708(16) 0.0148(5) Uani 1 1 d . . . . .
C8 C 0.3782(3) 0.42732(18) 0.69433(15) 0.0131(5) Uani 1 1 d . . . . .
C9 C 0.3883(4) 0.5327(2) 0.72611(16) 0.0166(5) Uani 1 1 d . . . . .
C10 C 0.4126(4) 0.5529(2) 0.81579(17) 0.0207(5) Uani 1 1 d . . . . .
C11 C 0.4319(3) 0.4681(2) 0.87503(17) 0.0194(5) Uani 1 1 d . . . . .
C12 C 0.4265(3) 0.3624(2) 0.84429(16) 0.0173(5) Uani 1 1 d . . . . .
C13 C 0.3987(3) 0.34218(18) 0.75456(16) 0.0158(5) Uani 1 1 d . . . . .
H1 H 0.565(5) 0.728(2) 0.175(2) 0.036(9) Uiso 1 1 d . . . . .
H2 H 0.581(5) 0.524(3) 0.373(2) 0.030(9) Uiso 1 1 d . . . . .
H3A H 0.629(5) 0.514(3) 0.534(2) 0.043(10) Uiso 1 1 d . . . . .
H3B H 0.745(5) 0.455(2) 0.613(2) 0.027(8) Uiso 1 1 d . . . . .
H3C H 0.786(4) 0.423(2) 0.5217(19) 0.023(8) Uiso 1 1 d . . . . .
H4 H 0.490(5) 0.864(3) 0.269(2) 0.029(8) Uiso 1 1 d . . . . .
H6 H 0.587(4) 0.298(2) 0.5886(18) 0.016(7) Uiso 1 1 d . . . . .
H7A H 0.247(4) 0.348(2) 0.5895(17) 0.010(6) Uiso 1 1 d . . . . .
H7B H 0.304(4) 0.473(2) 0.5625(19) 0.022(8) Uiso 1 1 d . . . . .
H9 H 0.378(4) 0.588(2) 0.6822(19) 0.022(7) Uiso 1 1 d . . . . .
H10 H 0.417(5) 0.629(3) 0.838(2) 0.042(10) Uiso 1 1 d . . . . .
H11 H 0.451(4) 0.482(2) 0.938(2) 0.025(8) Uiso 1 1 d . . . . .
H12 H 0.446(5) 0.300(2) 0.885(2) 0.031(9) Uiso 1 1 d . . . . .
H13 H 0.387(4) 0.266(2) 0.7314(19) 0.026(8) Uiso 1 1 d . . . . .


_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 1.354(2) . ?
O1 C1 1.232(3) . ?
O2 C2 1.236(3) . ?
N1 C1 1.360(3) . ?
N1 C4 1.370(3) . ?
N1 H1 0.97(3) . ?
N2 C2 1.377(3) . ?
N2 C1 1.379(3) . ?
N2 H2 0.90(3) . ?
C2 C3 1.443(3) . ?
C3 C4 1.338(3) . ?
C4 H4 0.95(3) . ?
O3 C5 1.254(3) . ?
O4 C5 1.257(3) . ?
N3 C6 1.492(3) . ?
N3 H3A 0.99(3) . ?
N3 H3B 0.95(3) . ?
N3 H3C 0.92(3) . ?
C5 C6 1.532(3) . ?
C6 C7 1.532(3) . ?
C6 H6 1.02(3) . ?
C7 C8 1.512(3) . ?
C7 H7A 1.01(3) . ?
C7 H7B 1.05(3) . ?
C8 C9 1.393(3) . ?
C8 C13 1.402(3) . ?
C9 C10 1.390(3) . ?
C9 H9 0.96(3) . ?
C10 C11 1.388(4) . ?
C10 H10 1.00(3) . ?
C11 C12 1.392(4) . ?
C11 H11 0.98(3) . ?
C12 C13 1.394(3) . ?
C12 H12 1.00(3) . ?
C13 H13 1.01(3) . ?

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
C1 N1 C4 122.36(19) . . ?
C1 N1 H1 116.5(18) . . ?
C4 N1 H1 120.9(19) . . ?
C2 N2 C1 126.39(19) . . ?
C2 N2 H2 116(2) . . ?
C1 N2 H2 117(2) . . ?
O1 C1 N1 123.3(2) . . ?
O1 C1 N2 120.74(19) . . ?
N1 C1 N2 115.94(19) . . ?
O2 C2 N2 121.5(2) . . ?
O2 C2 C3 125.5(2) . . ?
N2 C2 C3 113.04(19) . . ?
C4 C3 F1 120.9(2) . . ?
C4 C3 C2 122.2(2) . . ?
F1 C3 C2 116.88(19) . . ?
C3 C4 N1 120.0(2) . . ?
C3 C4 H4 125.6(19) . . ?
N1 C4 H4 114.3(19) . . ?
C6 N3 H3A 107(2) . . ?
C6 N3 H3B 114.2(19) . . ?
H3A N3 H3B 113(3) . . ?
C6 N3 H3C 107.9(19) . . ?
H3A N3 H3C 112(3) . . ?
H3B N3 H3C 103(3) . . ?
O3 C5 O4 125.2(2) . . ?
O3 C5 C6 118.41(19) . . ?
O4 C5 C6 116.4(2) . . ?
N3 C6 C7 110.41(18) . . ?
N3 C6 C5 108.46(17) . . ?
C7 C6 C5 113.77(18) . . ?
N3 C6 H6 105.9(16) . . ?
C7 C6 H6 110.7(17) . . ?
C5 C6 H6 107.3(15) . . ?
C8 C7 C6 111.80(19) . . ?
C8 C7 H7A 109.4(15) . . ?
C6 C7 H7A 108.9(15) . . ?
C8 C7 H7B 111.6(15) . . ?
C6 C7 H7B 109.0(16) . . ?
H7A C7 H7B 106(2) . . ?
C9 C8 C13 118.4(2) . . ?
C9 C8 C7 121.4(2) . . ?
C13 C8 C7 120.1(2) . . ?
C10 C9 C8 120.8(2) . . ?
C10 C9 H9 123.5(17) . . ?
C8 C9 H9 115.6(17) . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 H10 119(2) . . ?
C9 C10 H10 120(2) . . ?
C10 C11 C12 119.7(2) . . ?
C10 C11 H11 120.8(17) . . ?
C12 C11 H11 119.5(17) . . ?
C11 C12 C13 119.9(2) . . ?
C11 C12 H12 121.1(18) . . ?
C13 C12 H12 119.0(18) . . ?
C12 C13 C8 120.8(2) . . ?
C12 C13 H13 121.1(17) . . ?
C8 C13 H13 118.1(17) . . ?

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
C4 N1 C1 O1 177.6(2) . . . . ?
C4 N1 C1 N2 -2.1(3) . . . . ?
C2 N2 C1 O1 -179.4(2) . . . . ?
C2 N2 C1 N1 0.2(3) . . . . ?
C1 N2 C2 O2 -179.4(2) . . . . ?
C1 N2 C2 C3 0.8(3) . . . . ?
O2 C2 C3 C4 -179.9(2) . . . . ?
N2 C2 C3 C4 -0.1(3) . . . . ?
O2 C2 C3 F1 -0.8(4) . . . . ?
N2 C2 C3 F1 179.02(19) . . . . ?
F1 C3 C4 N1 179.3(2) . . . . ?
C2 C3 C4 N1 -1.6(4) . . . . ?
C1 N1 C4 C3 2.8(4) . . . . ?
O3 C5 C6 N3 -12.0(3) . . . . ?
O4 C5 C6 N3 166.98(18) . . . . ?
O3 C5 C6 C7 111.3(2) . . . . ?
O4 C5 C6 C7 -69.7(3) . . . . ?
N3 C6 C7 C8 -64.2(3) . . . . ?
C5 C6 C7 C8 173.56(18) . . . . ?
C6 C7 C8 C9 106.8(3) . . . . ?
C6 C7 C8 C13 -71.6(3) . . . . ?
C13 C8 C9 C10 -1.8(4) . . . . ?
C7 C8 C9 C10 179.7(2) . . . . ?
C8 C9 C10 C11 1.6(4) . . . . ?
C9 C10 C11 C12 -0.1(4) . . . . ?
C10 C11 C12 C13 -1.0(4) . . . . ?
C11 C12 C13 C8 0.8(4) . . . . ?
C9 C8 C13 C12 0.7(3) . . . . ?
C7 C8 C13 C12 179.2(2) . . . . ?

_refine_diff_density_max         0.182
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.063



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol/acetone/water'
