A novel drug–drug cocrystal of tegafur and myricetin: optimized properties of dissolution and tabletability
Zhang, Min; Gu, Dai-Lin; Zhen, Jian-Feng; Lu, Tong-Bu; Dai, Xia-Lin; Chen, Jia-Mei; CrystEngComm 25 (2023) 6171–6179; doi:10.1039/D3CE00794D

data_7247520
_publ_section_title
;
 A novel drug--drug cocrystal of tegafur and myricetin: optimized
 properties of dissolution and tabletability
;
_journal_issue                   44
_journal_name_full               CrystEngComm
_journal_page_first              6171
_journal_page_last               6179
_journal_paper_doi               10.1039/D3CE00794D
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C8 H9 F N2 O3, C15 H10 O8'
_chemical_formula_sum            'C23 H19 F N2 O11'
_chemical_formula_weight         518.40
_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   geom
_audit_creation_date             2023-09-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-09-21 deposited with the CCDC.	2023-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                109.530(2)
_cell_angle_beta                 108.436(2)
_cell_angle_gamma                100.043(2)
_cell_formula_units_Z            2
_cell_length_a                   9.2310(2)
_cell_length_b                   11.1587(2)
_cell_length_c                   11.8072(2)
_cell_measurement_reflns_used    14055
_cell_measurement_temperature    152(5)
_cell_measurement_theta_max      78.4780
_cell_measurement_theta_min      4.3600
_cell_volume                     1032.67(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      152(5)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -34.00  89.00   0.50    0.50    --    0.00  77.00  90.00  246
  2  \w    -28.00  89.00   0.50    0.50    --    0.00  57.00 150.00  234
  3  \w     -8.00 117.00   0.50    0.50    --   28.00  82.00 -47.96  250
  4  \w     30.00 153.00   0.50    0.64    --   64.00  77.00-159.28  246
  5  \w     17.00 140.00   0.50    0.64    --  106.20 -30.00-150.00  246
  6  \w     17.00 143.00   0.50    0.64    --  106.20 -82.00   0.00  252
  7  \w     72.00 196.00   0.50    0.64    --  106.20  77.00-180.00  248
  8  \w     17.00 136.00   0.50    0.64    --  106.20 -61.00 150.00  238
  9  \w     17.00 143.00   0.50    0.64    --  106.20 -82.00 -60.00  252
 10  \w     73.00 196.00   0.50    0.64    --  106.20  30.00-120.00  246
 11  \w     17.00 143.00   0.50    0.64    --  106.20 -82.00  60.00  252
 12  \w     78.00 196.00   0.50    0.64    --  106.20  45.00 120.00  236
 13  \w     73.00 196.00   0.50    0.64    --  106.20  30.00-150.00  246
 14  \w     17.00 136.00   0.50    0.64    --  106.20 -61.00   0.00  238
 15  \w     17.00 143.00   0.50    0.64    --  106.20 -82.00 150.00  252
 16  \w     17.00 143.00   0.50    0.64    --  106.20 -82.00-120.00  252
 17  \w     17.00 136.00   0.50    0.64    --  106.20 -61.00 -60.00  238
 18  \w     17.00 143.00   0.50    0.64    --  106.20 -82.00-180.00  252
 19  \w     78.00 196.00   0.50    0.64    --  106.20  45.00-150.00  236
 20  \w     17.00 143.00   0.50    0.64    --  106.20 -82.00 -30.00  252
 21  \w     70.00 196.00   0.50    0.64    --  106.20  82.00  90.00  252
 22  \w     16.00  59.00   0.50    0.50    --   52.00  81.00 121.68   86
 23  \w     18.00 141.00   0.50    0.50    --   52.00  77.00  28.31  246
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1035428000
_diffrn_orient_matrix_UB_12      -0.0889689000
_diffrn_orient_matrix_UB_13      -0.0346577000
_diffrn_orient_matrix_UB_21      0.1410578000
_diffrn_orient_matrix_UB_22      0.0913618000
_diffrn_orient_matrix_UB_23      0.1329593000
_diffrn_orient_matrix_UB_31      -0.0608055000
_diffrn_orient_matrix_UB_32      -0.0867848000
_diffrn_orient_matrix_UB_33      0.0633743000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0760
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18762
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        63.691
_diffrn_reflns_theta_max         63.691
_diffrn_reflns_theta_min         4.343
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.214
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27153
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         3393
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0460
_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^)+(0.0766P)^2^+0.6133P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1277
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3184
_reflns_number_total             3393
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00794d2.cif
_cod_data_source_block           tgf-yms
_cod_depositor_comments          'Adding full bibliography for 7247520.cif.'
_cod_database_code               7247520
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.953
_shelx_estimated_absorpt_t_min   0.888
_reflns_odcompleteness_completeness 99.31
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5A)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C8(H8A,H8B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C19(H19), C13(H13), C2(H2A), C9(H9A), C18(H18)
2.d Idealised tetrahedral OH refined as rotating group:
 O10(H10), O4(H4), O9(H9), O7(H7), O5(H5), O11(H11)
;
_shelx_res_checksum              84572
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.524
_oxdiff_exptl_absorpt_empirical_full_min 0.300