Intermolecular interactions and permeability of 5-fluorouracil cocrystals with a series of isomeric hydroxybenzoic acids: a combined theoretical and experimental study
Dai, Xia-Lin; Voronin, Alexander P.; Gao, Wei; Perlovich, German L.; Lu, Tong-Bu; Chen, Jia-Mei; CrystEngComm 21 (2019) 5095–; doi:10.1039/C9CE00661C

data_7233233
_publ_section_title
;
 Intermolecular interactions and permeability of 5-fluorouracil cocrystals
 with a series of isomeric hydroxybenzoic acids: a combined theoretical
 and experimental study
;
_journal_issue                   34
_journal_name_full               CrystEngComm
_journal_page_first              5095
_journal_paper_doi               10.1039/C9CE00661C
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         '0.5(C14 H12 O6), 2(C4 H3 F N2 O2)'
_chemical_formula_sum            'C15 H12 F2 N4 O7'
_chemical_formula_weight         398.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-04-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2018-12-17 deposited with the CCDC.    2019-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.902(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5354(8)
_cell_length_b                   6.9178(4)
_cell_length_c                   15.7237(8)
_cell_measurement_reflns_used    2271
_cell_measurement_temperature    150(10)
_cell_measurement_theta_max      65.1290
_cell_measurement_theta_min      2.7450
_cell_volume                     1569.61(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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      air
_diffrn_ambient_temperature      150(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5058
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
  1 omega  -35.00   67.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7938  -38.0000 -120.0000 102

  2 omega   11.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7938   57.0000 -120.0000 104

  3 omega   13.00   69.00   1.0000    1.1150
omega____ theta____ kappa____ phi______ frames
    -       90.6218  -30.0000    0.0000 56

  4 omega    7.00   84.00   1.0000    1.1150
omega____ theta____ kappa____ phi______ frames
    -       90.6218  -95.0000 -180.0000 77

  5 omega    7.00   84.00   1.0000    1.1150
omega____ theta____ kappa____ phi______ frames
    -       90.6218  -95.0000 -120.0000 77

  6 omega   16.00  121.00   1.0000    1.1150
omega____ theta____ kappa____ phi______ frames
    -       90.6218  -61.0000   90.0000 105

  7 omega   29.00  174.00   1.0000    1.1150
omega____ theta____ kappa____ phi______ frames
    -       90.6218   15.0000 -180.0000 145

  8 omega   11.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7938   57.0000  120.0000 104

  9 omega   11.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7938   57.0000    0.0000 104

 10 omega -157.00  -53.00   1.0000    1.1150
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -61.0000 -120.0000 104

 11 omega -161.00  -52.00   1.0000    1.1150
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -30.0000  -60.0000 109

 12 omega    7.00   84.00   1.0000    1.1150
omega____ theta____ kappa____ phi______ frames
    -       90.6218  -95.0000    0.0000 77

 13 omega   57.00  169.00   1.0000    1.1150
omega____ theta____ kappa____ phi______ frames
    -       90.6218   77.0000   30.0000 112

 14 omega -120.00  -44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7938  -77.0000  -60.0000 76

 15 omega  -99.00  -19.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7938  126.0000   90.0000 80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0901159000
_diffrn_orient_matrix_UB_12      0.0372816000
_diffrn_orient_matrix_UB_13      -0.0398274000
_diffrn_orient_matrix_UB_21      0.0543681000
_diffrn_orient_matrix_UB_22      0.0106734000
_diffrn_orient_matrix_UB_23      0.0902294000
_diffrn_orient_matrix_UB_31      0.0179573000
_diffrn_orient_matrix_UB_32      -0.2193760000
_diffrn_orient_matrix_UB_33      -0.0024266000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6426
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        65.569
_diffrn_reflns_theta_max         65.569
_diffrn_reflns_theta_min         5.669
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.318
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.627
_refine_diff_density_min         -0.566
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.0015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.903
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         1327
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0592
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1129P)^2^+3.7038P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1594
_refine_ls_wR_factor_ref         0.1806
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1022
_reflns_number_total             1327
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ce00661c2.cif
_cod_data_source_block           5fluorouracil-salicylic-acid-cocrystal
_cod_depositor_comments          'Adding full bibliography for 7233233.cif.'
_cod_database_code               7233233
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O3-C5
 1.2 with sigma of 0.005
 C5-O4
 1.32 with sigma of 0.005
 C6-C10
 1.42 with sigma of 0.005
 C10-C9
 1.42 with sigma of 0.005
 F1-O3_$3
 2.9 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
Uanis(C4) = Uanis(N2)
Uanis(C9) = Uanis(C21)
4. Others
 Fixed Sof: C10(0.5) H10(0.5) C8(0.5) H8(0.5) C5(0.5) O5(0.5) H5(0.5) O4(0.5)
 H4(0.5) O3(0.5) C6(0.5) C9(0.5) H9(0.5) C21(0.5) H21(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C8(H8), N2(H2), N1(H1), C2(H2A), C9(H9), C21(H21)
5.b Idealised tetrahedral OH refined as rotating group:
 O5(H5), O4(H4)
;
_shelx_res_checksum              5861
_olex2_submission_special_instructions 'No special instructions were received'