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_7057593
_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, C8 H16 O2'
_chemical_formula_sum            'C12 H20 F N3 O3'
_chemical_formula_weight         273.31
_chemical_name_common            '5-Fluorocytosine; 5-Flucytosine; 5-FC; 5FC-CA'
_chemical_name_systematic        '5-Fluorocytosine caprylic acid cocrystal'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-08-01
_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                81.892(3)
_cell_angle_beta                 85.884(3)
_cell_angle_gamma                84.460(3)
_cell_formula_units_Z            2
_cell_length_a                   5.2617(8)
_cell_length_b                   8.7066(14)
_cell_length_c                   15.710(2)
_cell_measurement_reflns_used    5600
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      33.30
_cell_measurement_theta_min      2.55
_cell_volume                     707.94(18)
_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_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            24416
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.550
_diffrn_reflns_theta_min         1.311
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9456
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0606 before and 0.0439 after correction. The Ratio of minimum to maximum transmission is 0.9456. The \l/2 correction factor is Not present.'
_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    1.282
_exptl_crystal_description       prism
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.067
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.622
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.133
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         5518
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0560
_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^)+(0.1220P)^2^+0.1090P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1817
_refine_ls_wR_factor_ref         0.2134
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3804
_reflns_number_total             5518
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8nj02647e2.cif
_cod_data_source_block           10830
_cod_depositor_comments
'Adding full bibliography for 7057591--7057593.cif.'
_cod_original_cell_volume        707.96(19)
_cod_database_code               7057593
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.985
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B), C12(H12A,H12B),
 C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7)
2.c X=CH2 refined with riding coordinates:
 N41(H41A,H41B)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'