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_7125061
_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         'C12 H10 N2, 2(C4 H3 F N2 O2)'
_chemical_formula_sum            'C20 H16 F2 N6 O4'
_chemical_formula_weight         442.39
_chemical_name_common            '5-fluorouracil, 2,2'-bpe'
_chemical_name_systematic
;
5-fluoro-1H,3H-pyrimidine-2,4-dione, 1,2-bis(2-pyridyl)ethylene
;
_chemical_properties_physical    Photo-sensitive
_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
_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                107.757(5)
_cell_angle_beta                 97.878(5)
_cell_angle_gamma                93.199(5)
_cell_formula_units_Z            1
_cell_length_a                   5.502(2)
_cell_length_b                   8.865(3)
_cell_length_c                   10.409(5)
_cell_measurement_reflns_used    1528
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      50.26
_cell_measurement_theta_min      7.517
_cell_volume                     476.4(3)
_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      190.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_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_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4836
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.341
_diffrn_reflns_theta_min         3.663
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_description       plate-like
_exptl_crystal_F_000             228
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   0.955
_exptl_transmission_factor_min   0.777
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         1732
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0441
_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^)+(0.0481P)^2^+0.2265P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1109
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1233
_reflns_number_total             1732
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc06570h2.cif
_cod_data_source_block           mcg1423
_cod_database_code               7125061
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.959
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3A), C4(H4), C6(H6), C7(H7)
;
_shelx_res_checksum              1240
_shelx_hkl_checksum              64517
_olex2_submission_special_instructions 'No special instructions were received'
_solvent_exptl_crystal_recrystallization_method methanol