Cocrystallization of 5-fluorouracil and L-phenylalanine: The first zwitterionic cocrystal of 5-fluorouracil with amino acid exhibiting the perfected in vitro/vivo pharmaceutical properties
Wang, Lin-Lin; Wang, Ling-Yang; Yu, Yueming; Li, Yan-Tuan; Wu, Zhi-Yong; Yan, Cui-Wei; CrystEngComm  (2020) –; doi:10.1039/D0CE00713G

data_7240794
_publ_section_title
;
 Cocrystallization of 5-fluorouracil and L-phenylalanine: The first
 zwitterionic cocrystal of 5-fluorouracil with amino acid exhibiting the
 perfected in vitro/vivo pharmaceutical properties
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00713G
_journal_year                    2020
_chemical_absolute_configuration rm
_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
_chemical_name_common            '5-fluorouracil L-phenylalanine'
_chemical_name_systematic
'5-Fluoropyrimidine-2,4(1H,3H)-dione 2-ammonio-3-phenylpropanoate'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2016/4
_audit_update_record
;
2019-12-16 deposited with the CCDC.	2020-06-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.00870(10)
_cell_length_b                   12.3981(2)
_cell_length_c                   15.1304(3)
_cell_measurement_reflns_used    2972
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.9370
_cell_measurement_theta_min      4.5780
_cell_volume                     1314.75(4)
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  Bruker
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4565
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.244
_diffrn_reflns_theta_min         4.611
_exptl_absorpt_coefficient_mu    1.038
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_description       column
_exptl_crystal_F_000             616
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethanol/acetone/water'
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.063
_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)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         2555
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0320
_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^)+(0.0365P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0754
_refine_ls_wR_factor_ref         0.0775
_reflns_Friedel_coverage         0.688
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.944
_reflns_number_gt                2421
_reflns_number_total             2555
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce00713g1.cif
_cod_data_source_block           shelx
_cod_database_code               7240794
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_min   0.746
_shelx_estimated_absorpt_t_max   0.950
_shelx_res_checksum              98898
_shelx_hkl_checksum              88977