A supramolecular adduct of tegafur and syringic acid: the first tegafur-nutraceutical cocrystal with perfected in vitro and in vivo characteristics as well as synergized anticancer activities
Yu, Yue-Ming; Yu, Ming-Chao; Wang, Ling-Yang; Li, Yan-Tuan; Wu, Zhi-Yong; Yan, Cui-Wei; New Journal of Chemistry 44 (2020) 15994–16005; doi:10.1039/D0NJ03033C

data_7059923
_publ_section_title
;
 A supramolecular adduct of tegafur and syringic acid: the first
 tegafur-nutraceutical cocrystal with perfected in vitro and in vivo
 characteristics as well as synergized anticancer activities
;
_journal_issue                   37
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              15994
_journal_page_last               16005
_journal_paper_doi               10.1039/D0NJ03033C
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C4 H4.5 F0.5 N O1.5, C4.5 H5 O2.5'
_chemical_formula_sum            'C8.5 H9.5 F0.5 N O4'
_chemical_formula_weight         199.17
_chemical_melting_point          181.0
_chemical_name_common            'Tegafur Syringic acid'
_chemical_name_systematic
'5-Fluoro-1-(tetrahydro-2-furyl)-uracil 4-hydroxy-3,5-dimethoxybenzoic acid'
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-04-15 deposited with the CCDC.	2020-08-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.260(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2818(13)
_cell_length_b                   6.7034(10)
_cell_length_c                   14.154(2)
_cell_measurement_reflns_used    4442
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.282
_cell_measurement_theta_min      3.039
_cell_volume                     876.9(2)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX area-detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15932
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_min         3.365
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_description       needle
_exptl_crystal_F_000             416
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol/water/ethyl acetate'
_exptl_crystal_size_max          0.457
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.102
_exptl_transmission_factor_max   0.7456
_exptl_transmission_factor_min   0.6970
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2177
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.140
_refine_ls_R_factor_all          0.1182
_refine_ls_R_factor_gt           0.0729
_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/[\s^2^(Fo^2^)+(0.0235P)^2^+1.4826P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1383
_refine_ls_wR_factor_ref         0.1523
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1439
_reflns_number_total             2177
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj03033c2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7059923.cif.'
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_original_formula_sum        'C8.50 H9.50 F0.50 N O4'
_cod_database_code               7059923
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.944
_shelx_estimated_absorpt_t_max   0.987
_shelx_res_checksum              87377