#------------------------------------------------------------------------------
#$Date: 2019-11-23 18:41:24 +0200 (Sat, 23 Nov 2019) $
#$Revision: 234480 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/50/7125061.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7125061
loop_
_publ_author_name
'Duncan, Andrew J. E.'
'Dudovitz, Roxanne L.'
'Dudovitz, Shawna J.'
'Stojaković, Jelena'
'Mariappan, S. V. Santhana'
'MacGillivray, Leonard R.'
_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/[σ²(Fo²)+(0.0481P)²+0.2265P] where P=(Fo²+2Fc²)/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 > 2σ(I)'
_cod_data_source_file            c6cc06570h2.cif
_cod_data_source_block           mcg1423
_cod_database_code               7125061
_shelxl_version_number           2014/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_olex2_submission_special_instructions 'No special instructions were received'
_solvent_exptl_crystal_recrystallization_method methanol
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
F1 F 1.0891(2) 0.24349(16) 0.33310(13) 0.0341(4) Uani 1 1 d .
O1 O 0.3673(3) 0.54262(18) 0.14586(15) 0.0288(4) Uani 1 1 d .
O2 O 0.7495(3) 0.38418(19) 0.49351(14) 0.0306(4) Uani 1 1 d .
N1 N 0.8130(4) 0.8523(2) 0.11141(19) 0.0323(5) Uani 1 1 d .
N2 N 0.7044(3) 0.4065(2) 0.11088(18) 0.0221(4) Uani 1 1 d .
H2 H 0.688(4) 0.418(3) 0.026(2) 0.027(6) Uiso 1 1 d .
N3 N 0.5628(3) 0.4626(2) 0.31819(17) 0.0230(4) Uani 1 1 d .
H3 H 0.449(4) 0.508(3) 0.370(2) 0.034(7) Uiso 1 1 d .
C1 C 0.9453(4) 0.7947(3) 0.2003(3) 0.0355(6) Uani 1 1 d .
H1 H 1.0779 0.7362 0.1708 0.043 Uiso 1 1 calc R
C2 C 0.9032(4) 0.8143(3) 0.3317(2) 0.0357(6) Uani 1 1 d .
H2A H 1.0032 0.7711 0.3908 0.043 Uiso 1 1 calc R
C3 C 0.7112(5) 0.8986(3) 0.3737(2) 0.0402(7) Uani 1 1 d .
H3A H 0.6747 0.9145 0.4632 0.048 Uiso 1 1 calc R
C4 C 0.5717(4) 0.9600(3) 0.2849(2) 0.0345(6) Uani 1 1 d .
H4 H 0.4387 1.0191 0.3129 0.041 Uiso 1 1 calc R
C5 C 0.6265(4) 0.9351(3) 0.1549(2) 0.0252(5) Uani 1 1 d .
C6 C 0.4768(4) 1.0024(3) 0.0612(2) 0.0304(6) Uani 1 1 d .
H6 H 0.3372 1.0526 0.0908 0.037 Uiso 1 1 calc R
C7 C 0.8891(4) 0.3285(3) 0.1576(2) 0.0238(5) Uani 1 1 d .
H7 H 1.0020 0.2809 0.0999 0.029 Uiso 1 1 calc R
C8 C 0.9090(4) 0.3198(2) 0.2845(2) 0.0231(5) Uani 1 1 d .
C9 C 0.7416(4) 0.3893(3) 0.3759(2) 0.0223(5) Uani 1 1 d .
C10 C 0.5350(4) 0.4747(2) 0.1879(2) 0.0213(5) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
C1 N1 C5 116.87(19) .
C7 N2 H2 122.2(13) .
C10 N2 H2 114.9(13) .
C10 N2 C7 122.86(18) .
C9 N3 H3 117.7(14) .
C9 N3 C10 126.77(17) .
C10 N3 H3 115.5(14) .
N1 C1 H1 117.6 .
N1 C1 C2 124.7(2) .
C2 C1 H1 117.6 .
C1 C2 H2A 121.3 .
C3 C2 C1 117.4(2) .
C3 C2 H2A 121.3 .
C2 C3 H3A 120.3 .
C2 C3 C4 119.4(2) .
C4 C3 H3A 120.3 .
C3 C4 H4 120.2 .
C3 C4 C5 119.5(2) .
C5 C4 H4 120.2 .
N1 C5 C4 122.1(2) .
N1 C5 C6 118.92(19) .
C4 C5 C6 119.01(19) .
C5 C6 H6 117.7 .
C6 C6 C5 124.6(3) 2_675
C6 C6 H6 117.7 2_675
N2 C7 H7 120.1 .
C8 C7 N2 119.83(18) .
C8 C7 H7 120.1 .
F1 C8 C9 116.75(18) .
C7 C8 F1 121.05(18) .
C7 C8 C9 122.21(19) .
O2 C9 N3 121.72(18) .
O2 C9 C8 125.19(19) .
N3 C9 C8 113.08(18) .
O1 C10 N2 123.11(19) .
O1 C10 N3 121.64(18) .
N2 C10 N3 115.25(18) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C8 1.357(2) .
O1 C10 1.231(2) .
O2 C9 1.234(2) .
N1 C1 1.339(3) .
N1 C5 1.344(3) .
N2 H2 0.92(2) .
N2 C7 1.377(3) .
N2 C10 1.360(3) .
N3 H3 0.92(2) .
N3 C9 1.378(3) .
N3 C10 1.381(3) .
C1 H1 0.9500 .
C1 C2 1.379(3) .
C2 H2A 0.9500 .
C2 C3 1.371(3) .
C3 H3A 0.9500 .
C3 C4 1.378(3) .
C4 H4 0.9500 .
C4 C5 1.381(3) .
C5 C6 1.475(3) .
C6 C6 1.322(5) 2_675
C6 H6 0.9500 .
C7 H7 0.9500 .
C7 C8 1.336(3) .
C8 C9 1.442(3) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O1 0.92(2) 1.91(2) 2.823(3) 174(2) 2_665
N3 H3 O2 0.92(2) 1.95(2) 2.863(2) 171(2) 2_666
C1 H1 O1 0.95 2.39 3.298(3) 160.7 1_655
C2 H2A O2 0.95 2.44 3.381(3) 169.4 2_766
C7 H7 N1 0.95 2.54 3.451(3) 161.9 2_765
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_4
F1 C8 C9 O2 -0.2(3) .
F1 C8 C9 N3 -179.25(18) .
N1 C1 C2 C3 0.2(4) .
N1 C5 C6 C6 -5.3(4) 2_675
N2 C7 C8 F1 179.93(19) .
N2 C7 C8 C9 0.3(3) .
C1 N1 C5 C4 -0.2(3) .
C1 N1 C5 C6 179.4(2) .
C1 C2 C3 C4 -0.4(4) .
C2 C3 C4 C5 0.3(4) .
C3 C4 C5 N1 0.0(4) .
C3 C4 C5 C6 -179.6(2) .
C4 C5 C6 C6 174.3(3) 2_675
C5 N1 C1 C2 0.1(4) .
C7 N2 C10 O1 -178.9(2) .
C7 N2 C10 N3 0.9(3) .
C7 C8 C9 O2 179.4(2) .
C7 C8 C9 N3 0.4(3) .
C9 N3 C10 O1 179.7(2) .
C9 N3 C10 N2 -0.2(3) .
C10 N2 C7 C8 -1.0(3) .
C10 N3 C9 O2 -179.6(2) .
C10 N3 C9 C8 -0.5(3) .
