Quantitative and regiocontrolled cross-photocycloaddition of the anticancer drug 5-fluorouracil achieved in a cocrystal.
Duncan, Andrew J. E.; Dudovitz, Roxanne L.; Dudovitz, Shawna J.; Stojaković, Jelena; Mariappan, S. V. Santhana; MacGillivray, Leonard R.; Chemical communications (Cambridge, England) 52 (2016) 13109–13111; doi:10.1039/c6cc06570h

data_7125062
_publ_section_title
;
 Quantitative and regiocontrolled cross-photocycloaddition of the
 anticancer drug 5-fluorouracil achieved in a cocrystal.
;
_journal_issue                   89
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              13109
_journal_page_last               13111
_journal_paper_doi               10.1039/c6cc06570h
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C16 H13 F N4 O2'
_chemical_formula_sum            'C16 H13 F N4 O2'
_chemical_formula_weight         312.30
_chemical_name_common
'5-fluoro-5,6-(bis(2-pyridyl)cyclobuta)uracil (fbpcu)'
_chemical_name_systematic
;
   6-fluoro-7,8-bis(2-pyridyl)-2,4-diazabicyclo[4.2.0]octa-3,5-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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-05-26
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-05-26 deposited with the CCDC.
2016-10-05 downloaded from the CCDC.
;
_cell_angle_alpha                98.513(5)
_cell_angle_beta                 102.020(5)
_cell_angle_gamma                101.749(5)
_cell_formula_units_Z            4
_cell_length_a                   7.8358(8)
_cell_length_b                   12.4452(12)
_cell_length_c                   15.6290(15)
_cell_measurement_reflns_used    5125
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      43.22
_cell_measurement_theta_min      5.478
_cell_volume                     1430.3(2)
_computing_cell_refinement       'apexII (Bruker AXS, 2010)'
_computing_data_collection       'apexII (Bruker AXS, 2010)'
_computing_data_reduction        'apexII (Bruker AXS, 2010)'
_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      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Nonius APEX II Kappa'
_diffrn_measurement_method       'CCD phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0596
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5257
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.426
_diffrn_reflns_theta_min         2.719
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0550 before and 0.0469 after correction.
 The Ratio of minimum to maximum transmission is 0.92.
 The \l/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.0660 before and 0.0538 after correction.
 The Ratio of minimum to maximum transmission not present.
 The \l/2 correction factor is Not present

Final HKLF 4 output contains 38011 reflections, Rint = 0.0532
 (14264 with I > 3sig(I), Rint = 0.0341)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_description       plate-like
_exptl_crystal_F_000             648
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   0.955
_exptl_transmission_factor_min   0.893
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     432
_refine_ls_number_reflns         5257
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0945
_refine_ls_R_factor_gt           0.0486
_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^)+(0.0535P)^2^+0.2055P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1175
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3446
_reflns_number_total             5257
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc06570h2.cif
_cod_data_source_block           mcg1545
_cod_database_code               7125062
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.971
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.6911(19) 0.3089(19)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7), C11(H11), C22(H22), C23(H23), C27(H27)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3A), C4(H4), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20), C29(H29), C30(H30), C31(H31), C32(H32)
;
_shelx_res_checksum              83681
_shelx_hkl_checksum              77913
_olex2_submission_special_instructions 'No special instructions were received'
_solvent_exptl_crystal_recrystallization_method isopropanol