Clues from cocrystals: a ternary solid, polymorphism, and rare supramolecular isomerism involving resveratrol and 5-fluorouracil.
Ortiz-de León, Celymar; MacGillivray, Leonard R.; Chemical communications (Cambridge, England) 57 (2021) 3809–3811; doi:10.1039/d0cc08388g

data_7128031
_publ_section_title
;
 Clues from cocrystals: a ternary solid, polymorphism, and rare
 supramolecular isomerism involving resveratrol and 5-fluorouracil.
;
_journal_issue                   31
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3809
_journal_page_last               3811
_journal_paper_doi               10.1039/d0cc08388g
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C4 H3 F N2 O2, C14 H12 O3, C12 H10 N2'
_chemical_formula_sum            'C30 H25 F N4 O5'
_chemical_formula_weight         540.54
_chemical_name_common            (resv).(bpe).(5-fu)
_chemical_name_systematic
'3,5,4'-trihydroxy-trans-stilbene, 1,2-bis(4-pyridyl)ethylene, 5-fluoro-1H,3H-pyrimidine-2,4-dione'
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2020-12-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-12-14 deposited with the CCDC.	2021-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                76.407(5)
_cell_angle_beta                 85.696(5)
_cell_angle_gamma                88.382(5)
_cell_formula_units_Z            2
_cell_length_a                   9.4819(9)
_cell_length_b                   10.6517(11)
_cell_length_c                   13.5060(14)
_cell_measurement_reflns_used    4772
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.73
_cell_measurement_theta_min      1.00
_cell_volume                     1322.1(2)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo, Scalepack (Otwinowski & Minor, 1997)'
_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      298.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0904
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7558
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.967
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_description       plate
_exptl_crystal_F_000             564
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   0.9925
_exptl_transmission_factor_min   0.9227
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         4645
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.969
_refine_ls_R_factor_all          0.1605
_refine_ls_R_factor_gt           0.0584
_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^)+(0.0777P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1677
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2073
_reflns_number_total             4645
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc08388g2.cif
_cod_data_source_block           mcg18177
_cod_depositor_comments
'Adding full bibliography for 7128030--7128031.cif.'
_cod_database_code               7128031
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.976
_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
 C6A-C7A \\sim C6B-C7B
 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(C7A) = Uanis(C7B)
Uanis(C6B) = Uanis(C6A)
4. Same fragment restrains
{C6B, C7B} sigma for 1-2: 0.02, 1-3: 0.04
{C6A, C6B} sigma for 1-2: 0.02, 1-3: 0.04
as
{C6A, C7A}
5. Others
 Sof(C6B)=Sof(H6B)=Sof(C7B)=Sof(H7B)=1-FVAR(1)
 Sof(C6A)=Sof(H6A)=Sof(C7A)=Sof(H7A)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 N3(H3A), N4(H4A), C17(H17), C15(H15), C20(H20), C23(H23), C13(H13), C26(H26),
 C22(H22), C19(H19), C28(H28), C25(H25), C10(H10), C11(H11), C12(H12), C5(H5),
 C9(H9), C4(H4), C6A(H6A), C7A(H7A), C6B(H6B), C7B(H7B), C2(H2A), C1(H1A)
6.b Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3), O1(H1)
;
_shelx_res_checksum              20227
_olex2_submission_special_instructions 'No special instructions were received'