The supramolecular self-assembly of 5-fluorouracil and caffeic acid through cocrystallization strategy opens up a new way for the development of synergistic antitumor pharmaceutical cocrystal
Yu, Yue-Ming; Wang, Ling-Yang; Bu, Fan-Zhi; Wang, Lin-Lin; Li, Yan-Tuan; Wang, Cheng; Wu, Zhi-Yong; CrystEngComm 22 (2020) 7992–8006; doi:10.1039/D0CE01297A

data_7241510
_publ_section_title
;
 The supramolecular self-assembly of 5-fluorouracil and caffeic acid
 through cocrystallization strategy opens up a new way for the development
 of synergistic antitumor pharmaceutical cocrystal
;
_journal_issue                   45
_journal_name_full               CrystEngComm
_journal_page_first              7992
_journal_page_last               8006
_journal_paper_doi               10.1039/D0CE01297A
_journal_volume                  22
_journal_year                    2020
_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
_chemical_melting_point          492
_chemical_name_common            '5-Fluorouracil Caffeic Acid'
_chemical_name_systematic
'5-Fluoropyrimidine-2,4(1H,3H)-dione 3-(3,4-dihydroxyphenyl)acrylic acid'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/4
_audit_update_record
;
2020-03-29 deposited with the CCDC.	2020-10-26 downloaded from the CCDC.
;
_cell_angle_alpha                99.753(5)
_cell_angle_beta                 96.384(5)
_cell_angle_gamma                98.812(5)
_cell_formula_units_Z            2
_cell_length_a                   6.9299(11)
_cell_length_b                   6.9584(10)
_cell_length_c                   15.946(2)
_cell_measurement_reflns_used    3336
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.834
_cell_measurement_theta_min      3.004
_cell_volume                     741.41(19)
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  Bruker
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0756
_diffrn_reflns_av_unetI/netI     0.0888
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15477
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.604
_diffrn_reflns_theta_min         3.005
_exptl_absorpt_coefficient_mu    0.137
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_description       column
_exptl_crystal_F_000             360
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol/water'
_exptl_crystal_size_max          0.379
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.027
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3419
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1550
_refine_ls_R_factor_gt           0.0688
_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^)+(0.0475P)^2^+0.6516P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1339
_refine_ls_wR_factor_ref         0.1582
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1810
_reflns_number_total             3419
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce01297a2.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        741.43(19)
_cod_database_code               7241510
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_min   0.950
_shelx_estimated_absorpt_t_max   0.996
_shelx_res_checksum              31216