Crystal engineering of a 1:1 5-fluorocytosine–4-hydroxybenzaldehyde cocrystal: insights from X-ray crystallography and Hirshfeld analysis
Sangavi, Marimuthu; Mohana, Marimuthu; Butcher, Ray J.; McMillen, Colin D.; Acta Crystallographica Section E Crystallographic Communications 81 (2025) –; doi:10.1107/S2056989025004463

data_2023515
_publ_section_title
;
 Crystal engineering of a 1:1 5-fluorocytosine--4-hydroxybenzaldehyde
 cocrystal: insights from X-ray crystallography and Hirshfeld analysis
;
_journal_coeditor_code           OI2017
_journal_issue                   6
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989025004463
_journal_volume                  81
_journal_year                    2025
_chemical_formula_iupac          'C4 H4 F N3 O, C7 H6 O2'
_chemical_formula_moiety         'C4 H4 F N3 O, C7 H6 O2'
_chemical_formula_sum            'C11 H10 F N3 O3'
_chemical_formula_weight         251.22
_chemical_name_common
;
5-Fluorocytosine--4-hydroxybenzaldehyde (1/1)
;
_chemical_name_systematic
;
4-Amino-5-fluoro-1<i>H</i>-pyrimidin-2-one--4-hydroxybenzaldehyde (1/1)
;
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                90
_cell_angle_beta                 94.1860(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.21260(10)
_cell_length_b                   9.66870(10)
_cell_length_c                   26.8628(5)
_cell_measurement_reflns_used    18043
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      76.1460
_cell_measurement_theta_min      3.2930
_cell_volume                     1091.21(3)
_computing_cell_refinement
;
CrysAlisPro 1.171.43.91a (Rigaku OD, 2023)
;
_computing_data_collection       'CrysAlisPro system (CCD 43.91a 64-bit (releas'
_computing_data_reduction
;
CrysAlisPro 1.171.43.91a (Rigaku OD, 2023)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020), Mercury (Macrae <i>et al.</i>, 2020)
and <i>POVRay</i> (Cason, 2004)
;
_computing_publication_material
;
PublCIF v1.9.21_c (Westrip, 2010)
;
_computing_structure_refinement
;
<i>SHELXL2019/2</i> (Sheldrick, 2015b)
;
_computing_structure_solution
;
<i>SHELXT</i> (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      297(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0096
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            19824
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.159
_diffrn_reflns_theta_min         3.299
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.072
_exptl_absorpt_correction_T_max  0.840
_exptl_absorpt_correction_T_min  0.782
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2023)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.266
_exptl_crystal_size_mid          0.205
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.189
_refine_ls_extinction_coef       0.0088(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
<i>SHELXL2019/2</i> (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2243
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0342
_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^)+(0.0563P)^2^+0.2241P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1010
_reflns_number_gt                2127
_reflns_number_total             2243
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            oi2017.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2023515
_shelx_hkl_checksum              67117
_shelx_res_checksum              64640