# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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 1972669'
loop_
_audit_author_name
_audit_author_address
'Yan-Tuan Li'
;School of Medicine and Pharmacy, Ocean University of China
China
;
_audit_update_record             
;
2020-04-15 deposited with the CCDC.	2020-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'5-Fluoro-1-(tetrahydro-2-furyl)-uracil 4-hydroxy-3,5-dimethoxybenzoic acid'
_chemical_name_common            'Tegafur Syringic acid'
_chemical_melting_point          181.0
_chemical_formula_moiety         'C4 H4.5 F0.5 N O1.5, C4.5 H5 O2.5'
_chemical_formula_sum            'C8.50 H9.50 F0.50 N O4'
_chemical_formula_weight         199.17

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      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'

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

_cell_length_a                   9.2818(13)
_cell_length_b                   6.7034(10)
_cell_length_c                   14.154(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.260(4)
_cell_angle_gamma                90
_cell_volume                     876.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4442
_cell_measurement_theta_min      3.039
_cell_measurement_theta_max      26.282

_exptl_crystal_description       needle
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   0.6970
_exptl_transmission_factor_max   0.7456
_exptl_crystal_size_max          0.457
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.102
_exptl_absorpt_coefficient_mu    0.127
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX area-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15932
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.365
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2177
_reflns_number_gt                1439
_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-2018/3 (Sheldrick, 2018)'
_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)+(0.0235P)²+1.4826P] 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         2177
_refine_ls_number_parameters     197
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1182
_refine_ls_R_factor_gt           0.0729
_refine_ls_wR_factor_ref         0.1523
_refine_ls_wR_factor_gt          0.1383
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_restrained_S_all      1.140
_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 0.6535(3) 0.250000 0.92075(18) 0.0531(8) Uani 1 2 d S T P . .
O1 O 0.9599(3) 0.250000 0.6201(2) 0.0413(8) Uani 1 2 d S T P . .
O2 O 0.5217(3) 0.250000 0.7403(2) 0.0464(9) Uani 1 2 d S T P . .
N1 N 0.9554(4) 0.250000 0.7805(3) 0.0499(12) Uani 1 2 d S T P . .
N2 N 0.7421(3) 0.250000 0.6816(2) 0.0312(9) Uani 1 2 d S T P . .
H2 H 0.705(2) 0.25000(2) 0.629(3) 0.037 Uiso 1 2 d R U P A .
C1 C 0.8908(4) 0.250000 0.6886(3) 0.0307(10) Uani 1 2 d S T P . .
C2 C 0.6540(4) 0.250000 0.7535(3) 0.0316(10) Uani 1 2 d S T P . .
C3 C 0.7317(5) 0.250000 0.8453(3) 0.0349(11) Uani 1 2 d S T P . .
C4 C 0.8740(5) 0.250000 0.8573(3) 0.0528(16) Uani 1 2 d S T P . .
O3 O 1.1463(5) 0.4512(8) 0.8660(4) 0.0406(12) Uani 0.5 1 d . U P A -1
C5 C 1.1153(7) 0.3096(8) 0.7933(4) 0.0337(17) Uani 0.5 1 d D . P A -1
H5A H 1.146915 0.358568 0.733331 0.040 Uiso 0.5 1 calc R U P A -1
C6 C 1.1965(9) 0.1213(13) 0.8242(6) 0.058(2) Uani 0.5 1 d D . P A -1
H6A H 1.290347 0.117155 0.799238 0.070 Uiso 0.5 1 calc R U P A -1
H6B H 1.141995 0.003427 0.803171 0.070 Uiso 0.5 1 calc R U P A -1
C7 C 1.2126(14) 0.135(3) 0.9328(7) 0.049(3) Uani 0.5 1 d D U P A -1
H7A H 1.124070 0.100306 0.960272 0.059 Uiso 0.5 1 calc R U P A -1
H7B H 1.291999 0.054753 0.960987 0.059 Uiso 0.5 1 calc R U P A -1
C8 C 1.245(2) 0.355(3) 0.9406(12) 0.096(6) Uani 0.5 1 d D U P A -1
H8A H 1.226690 0.404824 1.002817 0.116 Uiso 0.5 1 calc R U P A -1
H8B H 1.344906 0.381442 0.930349 0.116 Uiso 0.5 1 calc R U P A -1
H4 H 0.927(5) 0.250000 0.918(3) 0.049(14) Uiso 1 2 d S . P . .
O4 O 0.5551(3) 0.250000 0.5071(2) 0.0459(9) Uani 1 2 d S T P . .
O5 O 0.3526(3) 0.250000 0.5796(2) 0.0540(11) Uani 1 2 d S T P . .
O6 O -0.0499(3) 0.250000 0.31301(19) 0.0391(8) Uani 1 2 d S T P . .
O7 O 0.0831(3) 0.250000 0.15543(19) 0.0406(8) Uani 1 2 d S T P . .
H7 H -0.007609 0.250000 0.163108 0.061 Uiso 1 2 d R U P . .
O8 O 0.3655(3) 0.250000 0.1561(2) 0.0461(9) Uani 1 2 d S T P . .
C9 C 0.4240(5) 0.250000 0.5033(3) 0.0354(10) Uani 1 2 d S T P . .
C10 C 0.3302(4) 0.250000 0.4133(3) 0.0309(10) Uani 1 2 d S T P . .
C11 C 0.1804(5) 0.250000 0.4125(3) 0.0310(10) Uani 1 2 d S T P . .
C12 C 0.0978(4) 0.250000 0.3258(3) 0.0283(9) Uani 1 2 d S T P . .
C13 C 0.1630(4) 0.250000 0.2412(3) 0.0293(10) Uani 1 2 d S T P . .
C14 C 0.3132(5) 0.250000 0.2428(3) 0.0318(10) Uani 1 2 d S T P . .
C15 C 0.3964(5) 0.250000 0.3290(3) 0.0331(10) Uani 1 2 d S T P . .
C16 C -0.1284(5) 0.250000 0.3953(3) 0.0566(16) Uani 1 2 d S T P . .
H16A H -0.230334 0.250000 0.376181 0.085 Uiso 1 2 calc R U P . .
H16B H -0.103771 0.133069 0.432473 0.085 Uiso 0.5 1 calc R U P . .
H16C H -0.103771 0.366931 0.432473 0.085 Uiso 0.5 1 calc R U P . .
C17 C 0.5174(5) 0.250000 0.1536(4) 0.0584(16) Uani 1 2 d S T P . .
H17A H 0.540449 0.250000 0.088860 0.088 Uiso 1 2 calc R U P . .
H17B H 0.557515 0.366931 0.185157 0.088 Uiso 0.5 1 calc R U P . .
H17C H 0.557515 0.133069 0.185157 0.088 Uiso 0.5 1 calc R U P . .
H5 H 0.415(6) 0.250000 0.634(4) 0.063(17) Uiso 1 2 d S . P . .
H11 H 0.141(4) 0.250000 0.465(3) 0.027(11) Uiso 1 2 d S . P . .
H15 H 0.493(5) 0.250000 0.328(3) 0.037(13) Uiso 1 2 d S . P . .


_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 1.345(5) . y
O1 C1 1.211(5) . y
O2 C2 1.225(5) . y
N1 C4 1.379(6) . y
N1 C1 1.381(5) . y
N1 C5 1.531(7) . ?
N2 C2 1.363(5) . y
N2 C1 1.374(5) . y
N2 H2 0.80(4) . ?
C2 C3 1.427(6) . ?
C3 C4 1.316(6) . ?
C4 H4 0.95(5) . ?
O3 C5 1.410(7) . ?
O3 C8 1.479(17) . ?
C5 C6 1.514(7) . ?
C5 H5A 0.9800 . ?
C6 C7 1.534(9) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.505(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
O4 C9 1.212(5) . y
O5 C9 1.318(5) . y
O5 H5 0.92(5) . ?
O6 C12 1.366(5) . y
O6 C16 1.429(5) . y
O7 C13 1.363(5) . y
O7 H7 0.8587 . ?
O8 C14 1.360(5) . y
O8 C17 1.414(5) . y
C9 C10 1.476(6) . ?
C10 C11 1.389(6) . ?
C10 C15 1.391(6) . ?
C11 C12 1.386(6) . ?
C11 H11 0.86(4) . ?
C12 C13 1.392(6) . ?
C13 C14 1.392(6) . ?
C14 C15 1.383(6) . ?
C15 H15 0.90(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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 121.3(4) . . ?
C4 N1 C5 120.1(4) . . ?
C1 N1 C5 116.3(4) . . ?
C2 N2 C1 127.9(4) . . ?
C2 N2 H2 117.7 . . ?
C1 N2 H2 114.5 . . ?
O1 C1 N2 123.0(4) . . ?
O1 C1 N1 122.6(4) . . ?
N2 C1 N1 114.5(4) . . ?
O2 C2 N2 123.3(4) . . ?
O2 C2 C3 123.7(4) . . ?
N2 C2 C3 113.0(4) . . ?
C4 C3 F1 120.4(4) . . ?
C4 C3 C2 122.4(4) . . ?
F1 C3 C2 117.2(4) . . ?
C3 C4 N1 120.9(4) . . ?
C3 C4 H4 123(3) . . ?
N1 C4 H4 116(3) . . ?
C5 O3 C8 107.4(8) . . ?
O3 C5 C6 106.7(5) . . ?
O3 C5 N1 113.1(4) . . ?
C6 C5 N1 105.6(5) . . ?
O3 C5 H5A 110.4 . . ?
C6 C5 H5A 110.4 . . ?
N1 C5 H5A 110.4 . . ?
C5 C6 C7 103.8(8) . . ?
C5 C6 H6A 111.0 . . ?
C7 C6 H6A 111.0 . . ?
C5 C6 H6B 111.0 . . ?
C7 C6 H6B 111.0 . . ?
H6A C6 H6B 109.0 . . ?
C8 C7 C6 97.7(12) . . ?
C8 C7 H7A 112.2 . . ?
C6 C7 H7A 112.2 . . ?
C8 C7 H7B 112.2 . . ?
C6 C7 H7B 112.2 . . ?
H7A C7 H7B 109.8 . . ?
O3 C8 C7 105.5(14) . . ?
O3 C8 H8A 110.6 . . ?
C7 C8 H8A 110.6 . . ?
O3 C8 H8B 110.6 . . ?
C7 C8 H8B 110.6 . . ?
H8A C8 H8B 108.8 . . ?
C9 O5 H5 111(3) . . ?
C12 O6 C16 118.2(3) . . ?
C13 O7 H7 110.3 . . ?
C14 O8 C17 117.5(4) . . ?
O4 C9 O5 122.8(4) . . ?
O4 C9 C10 123.3(4) . . ?
O5 C9 C10 113.9(4) . . ?
C11 C10 C15 120.9(4) . . ?
C11 C10 C9 121.2(4) . . ?
C15 C10 C9 117.9(4) . . ?
C12 C11 C10 118.7(4) . . ?
C12 C11 H11 122(3) . . ?
C10 C11 H11 120(3) . . ?
O6 C12 C11 125.8(4) . . ?
O6 C12 C13 113.3(3) . . ?
C11 C12 C13 120.8(4) . . ?
O7 C13 C12 121.5(4) . . ?
O7 C13 C14 118.5(4) . . ?
C12 C13 C14 120.0(4) . . ?
O8 C14 C15 125.4(4) . . ?
O8 C14 C13 115.2(4) . . ?
C15 C14 C13 119.4(4) . . ?
C14 C15 C10 120.1(4) . . ?
C14 C15 H15 117(3) . . ?
C10 C15 H15 123(3) . . ?
O6 C16 H16A 109.5 . . ?
O6 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O6 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O8 C17 H17A 109.5 . . ?
O8 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O8 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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 180.000(1) . . . . ?
C2 N2 C1 N1 0.000(2) . . . . ?
C4 N1 C1 O1 180.000(1) . . . . ?
C5 N1 C1 O1 16.9(2) . . . . ?
C4 N1 C1 N2 0.000(2) . . . . ?
C5 N1 C1 N2 -163.1(2) . . . . ?
C1 N2 C2 O2 180.000(1) . . . . ?
C1 N2 C2 C3 0.000(2) . . . . ?
O2 C2 C3 C4 180.000(2) . . . . ?
N2 C2 C3 C4 0.000(2) . . . . ?
O2 C2 C3 F1 0.000(2) . . . . ?
N2 C2 C3 F1 180.000(1) . . . . ?
F1 C3 C4 N1 180.000(2) . . . . ?
C2 C3 C4 N1 0.000(2) . . . . ?
C1 N1 C4 C3 0.000(2) . . . . ?
C5 N1 C4 C3 162.5(2) . . . . ?
C8 O3 C5 C6 0.2(11) . . . . y
C8 O3 C5 N1 115.8(9) . . . . ?
C4 N1 C5 O3 -31.0(5) . . . . y
C1 N1 C5 O3 132.3(4) . . . . y
C4 N1 C5 C6 85.3(5) . . . . y
C1 N1 C5 C6 -111.4(4) . . . . y
O3 C5 C6 C7 26.0(10) . . . . y
N1 C5 C6 C7 -94.6(7) . . . . ?
C5 C6 C7 C8 -40.0(13) . . . . y
C5 O3 C8 C7 -27.1(16) . . . . y
C6 C7 C8 O3 40.9(15) . . . . y
O4 C9 C10 C11 180.000(1) . . . . ?
O5 C9 C10 C11 0.000(1) . . . . ?
O4 C9 C10 C15 0.000(1) . . . . ?
O5 C9 C10 C15 180.000(1) . . . . ?
C15 C10 C11 C12 0.000(1) . . . . ?
C9 C10 C11 C12 180.000(1) . . . . ?
C16 O6 C12 C11 0.000(1) . . . . ?
C16 O6 C12 C13 180.000(0) . . . . ?
C10 C11 C12 O6 180.000(1) . . . . ?
C10 C11 C12 C13 0.000(1) . . . . ?
O6 C12 C13 O7 0.000(1) . . . . ?
C11 C12 C13 O7 180.000(1) . . . . ?
O6 C12 C13 C14 180.000(1) . . . . ?
C11 C12 C13 C14 0.000(1) . . . . ?
C17 O8 C14 C15 0.000(1) . . . . ?
C17 O8 C14 C13 180.000(0) . . . . ?
O7 C13 C14 O8 0.000(1) . . . . ?
C12 C13 C14 O8 180.000(0) . . . . ?
O7 C13 C14 C15 180.000(1) . . . . ?
C12 C13 C14 C15 0.000(1) . . . . ?
O8 C14 C15 C10 180.000(1) . . . . ?
C13 C14 C15 C10 0.000(1) . . . . ?
C11 C10 C15 C14 0.000(1) . . . . ?
C9 C10 C15 C14 180.000(1) . . . . ?

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
_geom_hbond_publ_flag
N2 H2 O4 0.80 2.11 2.886(5) 164.6 . yes
O5 H5 O2 0.92(5) 1.73(6) 2.643(4) 175(5) . yes
O7 H7 O3 0.86 2.40 2.919(6) 119.7 2_646 yes
O7 H7 O3 0.86 2.40 2.919(6) 119.7 3_666 yes
C6 H6A O2 0.97 2.54 3.453(10) 157.8 1_655 yes
C6 H6B O6 0.97 2.46 3.366(8) 155.0 2_646 yes

_refine_diff_density_max         0.222
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.056



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