Avoiding irreversible 5-fluorocytosine hydration via supramolecular synthesis of pharmaceutical cocrystals
Souza, Matheus S.; Diniz, Luan F.; Vogt, Lautaro; Carvalho, Paulo S.; D’vries, Richard F.; Ellena, Javier; New Journal of Chemistry 42 (2018) 14994–; doi:10.1039/C8NJ02647E

data_7057592
_publ_section_title
;
 Avoiding irreversible 5-fluorocytosine hydration via supramolecular
 synthesis of pharmaceutical cocrystals
;
_journal_issue                   18
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              14994
_journal_paper_doi               10.1039/C8NJ02647E
_journal_volume                  42
_journal_year                    2018
_chemical_formula_moiety         'C4 H4 F N3 O, C7 H7 N O2'
_chemical_formula_sum            'C11 H11 F N4 O3'
_chemical_formula_weight         266.24
_chemical_name_common
'5-Fluorocytosine; 5-Flucytosine; 5-FC; 5FC-PABA'
_chemical_name_systematic
'5-Fluorocytosine p-aminobenzoic acid cocrystal'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-08-02
_audit_creation_method
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_audit_update_record
;
2018-07-17 deposited with the CCDC.
2018-07-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.567(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.8695(3)
_cell_length_b                   24.4911(16)
_cell_length_c                   9.8792(6)
_cell_measurement_reflns_used    5687
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.3520
_cell_measurement_theta_min      4.1420
_cell_volume                     1167.93(13)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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_temperature      298(2)
_diffrn_detector_area_resol_mean 5.2923
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_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    -17.00  84.00   1.00   20.00    --   11.26  57.00 -60.00  101
  2  \w    -84.00  17.00   1.00   20.00    --  -11.49 -57.00   0.00  101
  3  \w    -40.00  62.00   1.00   20.00    --  -11.49  57.00 150.00  102
  4  \w    -63.00  36.00   1.00   20.00    --   11.26 -38.00 -60.00   99
  5  \w    -20.00  52.00   1.00   20.00    --   11.26 -99.00 -90.00   72
  6  \w     34.00  98.00   1.00   20.00    --   11.26-178.00 150.00   64
  7  \w    -13.00  45.00   1.00   20.00    --   11.26  38.00-150.00   58
  8  \w    -20.00  29.00   1.00   20.00    --  -11.49 -99.00 150.00   49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0642
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            19318
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         3.925
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68237
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_description       needle
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2671
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0565
_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^)+(0.0615P)^2^+0.6472P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1426
_refine_ls_wR_factor_ref         0.1500
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2204
_reflns_number_total             2671
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8nj02647e2.cif
_cod_data_source_block           5fc-paba
_cod_depositor_comments
'Adding full bibliography for 7057591--7057593.cif.'
_cod_original_cell_volume        1167.92(13)
_cod_database_code               7057592
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Rigid body (RIGU) restrains
 C9, C8, C13', C12', C11, C10
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Fixed Sof: C12'(0.45) H12'(0.45) C13'(0.45) H13'(0.45) C9(0.55) H9(0.55)
 C10(0.55) H10(0.55) C13(0.55) H13(0.55) C12(0.55) H12(0.55) C9'(0.45)
 H9'(0.45) C10'(0.45) H10'(0.45)
4.a Rotating group:
 N4(H4A,H4B)
4.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C12'(H12'), C13'(H13'), C9(H9), C10(H10), C13(H13), C12(H12),
 C9'(H9'), C10'(H10')
4.c X=CH2 refined with riding coordinates:
 N41(H41A,H41B)
4.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
;