# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5
_database_code_depnum_ccdc_archive 'CCDC 1543788'
_audit_update_record             
;
2017-04-13 deposited with the CCDC.
2018-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        'Flucytosine/2,3-dihydroxybenzoic acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H14 F2 N6 O6'
_chemical_formula_weight         412.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1192(5)
_cell_length_b                   10.0601(5)
_cell_length_c                   10.0983(5)
_cell_angle_alpha                105.212(2)
_cell_angle_beta                 112.720(2)
_cell_angle_gamma                95.794(2)
_cell_volume                     803.01(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2707
_cell_measurement_theta_min      5.027
_cell_measurement_theta_max      64.612

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    1.299
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.792
_exptl_absorpt_correction_T_max  0.845
_exptl_absorpt_process_details   '(sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  proteum2
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9873
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         5.027
_diffrn_reflns_theta_max         64.612
_diffrn_reflns_theta_full        64.612
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             2707
_reflns_number_gt                2362
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1799P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2636
_refine_ls_number_parameters     303
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0652
_refine_ls_wR_factor_ref         0.2010
_refine_ls_wR_factor_gt          0.1901
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F2 F 0.29002(15) -0.00017(13) 0.42135(14) 0.0240(4) Uani 1 1 d . . . . .
F1 F 1.00219(17) 0.75730(13) 0.53757(15) 0.0311(4) Uani 1 1 d . . . . .
O3 O 0.55508(17) 0.56660(15) -0.09656(16) 0.0198(4) Uani 1 1 d . . . . .
H10 H 0.5583 0.5308 -0.1780 0.030 Uiso 1 1 calc R U . . .
O4 O 0.58056(19) 0.71999(17) 0.18093(18) 0.0230(4) Uani 1 1 d . . . . .
O6 O 0.61854(17) 0.17572(14) 0.13865(15) 0.0197(4) Uani 1 1 d . . . . .
O1 O 0.85825(18) 0.69224(16) -0.27447(16) 0.0234(4) Uani 1 1 d . . . . .
O2 O 0.65312(19) 0.53618(15) -0.29430(17) 0.0241(4) Uani 1 1 d . . . . .
O5 O 0.84449(18) 0.37101(15) -0.00030(16) 0.0213(4) Uani 1 1 d . . . . .
N6 N 0.8142(2) 0.43966(17) 0.21945(19) 0.0170(5) Uani 1 1 d . . . . .
H3 H 0.7444 0.3616 0.1896 0.020 Uiso 1 1 calc R U . . .
N1 N 0.4394(2) 0.00564(18) 0.1430(2) 0.0180(5) Uani 1 1 d . . . . .
N4 N 0.7723(2) 0.5107(2) 0.4376(2) 0.0193(5) Uani 1 1 d . . . . .
N5 N 1.0013(2) 0.57988(18) 0.1809(2) 0.0188(5) Uani 1 1 d . . . . .
N2 N 0.5635(2) 0.22143(17) 0.34542(19) 0.0178(5) Uani 1 1 d . . . . .
N3 N 0.5018(2) 0.2583(2) 0.5508(2) 0.0230(5) Uani 1 1 d . . . . .
C9 C 0.7667(3) 0.6501(2) -0.2225(2) 0.0171(5) Uani 1 1 d . . . . .
C5 C 0.5436(2) 0.1372(2) 0.2083(2) 0.0166(5) Uani 1 1 d . . . . .
C13 C 0.8011(3) 0.8917(2) 0.2109(2) 0.0198(5) Uani 1 1 d . . . . .
C15 C 0.6743(2) 0.6866(2) -0.0149(2) 0.0159(5) Uani 1 1 d . . . . .
C12 C 0.9102(2) 0.9376(2) 0.1577(2) 0.0206(5) Uani 1 1 d . . . . .
H13 H 0.9882 1.0221 0.2150 0.025 Uiso 1 1 calc R U . . .
C6 C 0.4805(2) 0.1768(2) 0.4156(2) 0.0181(5) Uani 1 1 d . . . . .
C1 C 1.0418(3) 0.6801(2) 0.3177(2) 0.0189(5) Uani 1 1 d . . . . .
C10 C 0.7829(2) 0.7328(2) -0.0685(2) 0.0161(5) Uani 1 1 d . . . . .
C3 C 0.8460(2) 0.5348(2) 0.3554(2) 0.0170(5) Uani 1 1 d . . . . .
C4 C 0.8849(2) 0.4580(2) 0.1249(2) 0.0174(5) Uani 1 1 d . . . . .
C14 C 0.6854(2) 0.7659(2) 0.1267(2) 0.0171(5) Uani 1 1 d . . . . .
C11 C 0.9025(3) 0.8579(2) 0.0199(2) 0.0193(5) Uani 1 1 d . . . . .
C7 C 0.3714(2) 0.0408(2) 0.3458(2) 0.0188(5) Uani 1 1 d . . . . .
C2 C 0.9665(3) 0.6609(2) 0.4030(2) 0.0195(5) Uani 1 1 d . . . . .
C8 C 0.3533(3) -0.0426(2) 0.2110(2) 0.0195(5) Uani 1 1 d . . . . .
H7 H 0.2832 -0.1318 0.1647 0.023 Uiso 1 1 calc R U . . .
H1 H 1.125(3) 0.763(3) 0.343(3) 0.028(6) Uiso 1 1 d . . . . .
H9 H 0.557(3) 0.342(3) 0.581(3) 0.027(7) Uiso 1 1 d . . . . .
H4 H 0.706(3) 0.427(3) 0.409(3) 0.030(7) Uiso 1 1 d . . . . .
H8 H 0.449(3) 0.231(3) 0.594(3) 0.027(7) Uiso 1 1 d . . . . .
H12 H 0.799(3) 0.945(3) 0.306(3) 0.021(6) Uiso 1 1 d . . . . .
H5 H 0.803(3) 0.576(3) 0.542(4) 0.037(8) Uiso 1 1 d . . . . .
H14 H 0.975(3) 0.882(2) -0.022(3) 0.022(6) Uiso 1 1 d . . . . .
H2 H 1.049(3) 0.599(3) 0.129(3) 0.030(7) Uiso 1 1 d . . . . .
H6 H 0.421(3) -0.054(3) 0.051(4) 0.030(7) Uiso 1 1 d . . . . .
H11 H 0.528(3) 0.648(3) 0.126(3) 0.028(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F2 C7 1.358(3) . ?
F1 C2 1.340(3) . ?
O3 C15 1.356(3) . ?
O3 H10 0.8200 . ?
O4 C14 1.369(3) . ?
O4 H11 0.76(3) . ?
O6 C5 1.254(3) . ?
O1 C9 1.240(3) . ?
O2 C9 1.287(3) . ?
O5 C4 1.222(3) . ?
N6 C3 1.353(3) . ?
N6 C4 1.381(3) . ?
N6 H3 0.8600 . ?
N1 C8 1.356(3) . ?
N1 C5 1.376(3) . ?
N1 H6 0.91(3) . ?
N4 C3 1.305(3) . ?
N4 H4 0.89(3) . ?
N4 H5 0.99(3) . ?
N5 C4 1.364(3) . ?
N5 C1 1.364(3) . ?
N5 H2 0.85(3) . ?
N2 C6 1.338(3) . ?
N2 C5 1.352(3) . ?
N3 C6 1.322(3) . ?
N3 H9 0.84(3) . ?
N3 H8 0.84(3) . ?
C9 C10 1.500(3) . ?
C13 C14 1.382(3) . ?
C13 C12 1.393(3) . ?
C13 H12 0.98(3) . ?
C15 C10 1.393(3) . ?
C15 C14 1.402(3) . ?
C12 C11 1.384(3) . ?
C12 H13 0.9300 . ?
C6 C7 1.427(3) . ?
C1 C2 1.329(3) . ?
C1 H1 0.97(3) . ?
C10 C11 1.397(3) . ?
C3 C2 1.428(3) . ?
C11 H14 0.96(3) . ?
C7 C8 1.336(3) . ?
C8 H7 0.9300 . ?

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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O3 H10 109.5 . . ?
C14 O4 H11 109(2) . . ?
C3 N6 C4 125.19(16) . . ?
C3 N6 H3 117.4 . . ?
C4 N6 H3 117.4 . . ?
C8 N1 C5 122.07(19) . . ?
C8 N1 H6 115.3(17) . . ?
C5 N1 H6 122.6(17) . . ?
C3 N4 H4 120.2(19) . . ?
C3 N4 H5 121.6(17) . . ?
H4 N4 H5 117(3) . . ?
C4 N5 C1 123.07(19) . . ?
C4 N5 H2 120.7(18) . . ?
C1 N5 H2 116.2(18) . . ?
C6 N2 C5 119.75(17) . . ?
C6 N3 H9 115.9(19) . . ?
C6 N3 H8 119.5(19) . . ?
H9 N3 H8 124(3) . . ?
O1 C9 O2 123.58(19) . . ?
O1 C9 C10 120.60(18) . . ?
O2 C9 C10 115.82(18) . . ?
O6 C5 N2 121.59(18) . . ?
O6 C5 N1 118.78(19) . . ?
N2 C5 N1 119.6(2) . . ?
C14 C13 C12 120.2(2) . . ?
C14 C13 H12 115.9(14) . . ?
C12 C13 H12 123.9(14) . . ?
O3 C15 C10 122.04(19) . . ?
O3 C15 C14 118.02(19) . . ?
C10 C15 C14 119.93(18) . . ?
C11 C12 C13 120.13(18) . . ?
C11 C12 H13 119.9 . . ?
C13 C12 H13 119.9 . . ?
N3 C6 N2 119.75(18) . . ?
N3 C6 C7 120.2(2) . . ?
N2 C6 C7 120.04(19) . . ?
C2 C1 N5 119.92(19) . . ?
C2 C1 H1 125.1(17) . . ?
N5 C1 H1 114.9(17) . . ?
C15 C10 C11 119.61(19) . . ?
C15 C10 C9 119.65(18) . . ?
C11 C10 C9 120.72(19) . . ?
N4 C3 N6 121.65(18) . . ?
N4 C3 C2 122.7(2) . . ?
N6 C3 C2 115.61(19) . . ?
O5 C4 N5 122.88(19) . . ?
O5 C4 N6 121.95(17) . . ?
N5 C4 N6 115.17(18) . . ?
O4 C14 C13 119.93(19) . . ?
O4 C14 C15 120.20(17) . . ?
C13 C14 C15 119.86(19) . . ?
C12 C11 C10 120.2(2) . . ?
C12 C11 H14 124.6(15) . . ?
C10 C11 H14 115.2(15) . . ?
C8 C7 F2 122.01(19) . . ?
C8 C7 C6 120.0(2) . . ?
F2 C7 C6 117.99(19) . . ?
C1 C2 F1 121.68(18) . . ?
C1 C2 C3 121.0(2) . . ?
F1 C2 C3 117.35(19) . . ?
C7 C8 N1 118.50(19) . . ?
C7 C8 H7 120.7 . . ?
N1 C8 H7 120.7 . . ?

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
O4 H11 O3 0.76(3) 2.30(3) 2.728(2) 117(3) .
N1 H6 O6 0.91(3) 1.85(3) 2.760(2) 179(3) 2_655
N5 H2 O5 0.85(3) 1.96(3) 2.804(2) 176(3) 2_765
N4 H4 N2 0.89(3) 2.12(3) 3.008(3) 176(2) .
C1 H1 F2 0.97(3) 2.43(3) 3.391(3) 167(2) 1_665
O3 H10 O2 0.82 1.71 2.448(2) 148.0 .
N1 H6 O6 0.91(3) 1.85(3) 2.760(2) 179(3) 2_655
N5 H2 O5 0.85(3) 1.96(3) 2.804(2) 176(3) 2_765
N4 H5 O1 0.99(3) 1.76(3) 2.751(2) 180(3) 1_556
N3 H8 O4 0.84(3) 2.32(3) 3.041(3) 144(2) 2_666
N4 H4 N2 0.89(3) 2.12(3) 3.008(3) 176(2) .
N3 H9 O2 0.84(3) 1.92(3) 2.725(3) 159(3) 1_556
C1 H1 F2 0.97(3) 2.43(3) 3.391(3) 167(2) 1_665
O3 H10 O2 0.82 1.71 2.448(2) 148.0 .
N1 H6 O6 0.91(3) 1.85(3) 2.760(2) 179(3) 2_655
O4 H11 O3 0.76(3) 2.30(3) 2.728(2) 117(3) .
N5 H2 O5 0.85(3) 1.96(3) 2.804(2) 176(3) 2_765
C8 H7 O5 0.93 2.40 3.292(3) 161.3 2_655
N6 H3 O6 0.86 1.92 2.772(2) 170.7 .
N4 H4 N2 0.89(3) 2.12(3) 3.008(3) 176(2) .
C1 H1 F2 0.97(3) 2.43(3) 3.391(3) 167(2) 1_665
N1 H6 O6 0.91(3) 1.85(3) 2.760(2) 179(3) 2_655
O4 H11 O3 0.76(3) 2.30(3) 2.728(2) 117(3) .
N5 H2 O5 0.85(3) 1.96(3) 2.804(2) 176(3) 2_765
C8 H7 O5 0.93 2.40 3.292(3) 161.3 2_655
N6 H3 O6 0.86 1.92 2.772(2) 170.7 .
N4 H4 N2 0.89(3) 2.12(3) 3.008(3) 176(2) .
C1 H1 F2 0.97(3) 2.43(3) 3.391(3) 167(2) 1_665
C1 H1 F2 0.97(3) 2.43(3) 3.391(3) 167(2) 1_665
N3 H9 O2 0.84(3) 1.92(3) 2.725(3) 159(3) 1_556
N4 H4 N2 0.89(3) 2.12(3) 3.008(3) 176(2) .
N6 H3 O6 0.86 1.92 2.772(2) 170.7 .
N3 H8 O4 0.84(3) 2.32(3) 3.041(3) 144(2) 2_666
C8 H7 O5 0.93 2.40 3.292(3) 161.3 2_655
N4 H5 O1 0.99(3) 1.76(3) 2.751(2) 180(3) 1_556
N4 H5 O2 0.99(3) 2.60(3) 3.247(3) 123(2) 1_556
N5 H2 O5 0.85(3) 1.96(3) 2.804(2) 176(3) 2_765
O4 H11 O3 0.76(3) 2.30(3) 2.728(2) 117(3) .
O4 H11 O3 0.76(3) 2.12(3) 2.783(2) 147(3) 2_665
N1 H6 O6 0.91(3) 1.85(3) 2.760(2) 179(3) 2_655
O3 H10 O2 0.82 1.71 2.448(2) 148.0 .
C1 H1 F2 0.97(3) 2.43(3) 3.391(3) 167(2) 1_665
N3 H9 O2 0.84(3) 1.92(3) 2.725(3) 159(3) 1_556
N4 H4 N2 0.89(3) 2.12(3) 3.008(3) 176(2) .
N6 H3 O6 0.86 1.92 2.772(2) 170.7 .
N3 H8 O4 0.84(3) 2.32(3) 3.041(3) 144(2) 2_666
C8 H7 O5 0.93 2.40 3.292(3) 161.3 2_655
N4 H5 O1 0.99(3) 1.76(3) 2.751(2) 180(3) 1_556
N4 H5 O2 0.99(3) 2.60(3) 3.247(3) 123(2) 1_556
N5 H2 O5 0.85(3) 1.96(3) 2.804(2) 176(3) 2_765
O4 H11 O3 0.76(3) 2.30(3) 2.728(2) 117(3) .
O4 H11 O3 0.76(3) 2.12(3) 2.783(2) 147(3) 2_665
N1 H6 O6 0.91(3) 1.85(3) 2.760(2) 179(3) 2_655
C1 H1 F2 0.97(3) 2.43(3) 3.391(3) 167(2) 1_665
N4 H4 N2 0.89(3) 2.12(3) 3.008(3) 176(2) .
N6 H3 O6 0.86 1.92 2.772(2) 170.7 .
C8 H7 O5 0.93 2.40 3.292(3) 161.3 2_655
N5 H2 O5 0.85(3) 1.96(3) 2.804(2) 176(3) 2_765
O4 H11 O3 0.76(3) 2.30(3) 2.728(2) 117(3) .
N1 H6 O6 0.91(3) 1.85(3) 2.760(2) 179(3) 2_655
O3 H10 O2 0.82 1.71 2.448(2) 148.0 .
C1 H1 F2 0.97(3) 2.43(3) 3.391(3) 167(2) 1_665
N3 H9 O2 0.84(3) 1.92(3) 2.725(3) 159(3) 1_556
N4 H4 N2 0.89(3) 2.12(3) 3.008(3) 176(2) .
N3 H8 O4 0.84(3) 2.32(3) 3.041(3) 144(2) 2_666
N4 H5 O1 0.99(3) 1.76(3) 2.751(2) 180(3) 1_556
N4 H5 O2 0.99(3) 2.60(3) 3.247(3) 123(2) 1_556
N5 H2 O5 0.85(3) 1.96(3) 2.804(2) 176(3) 2_765
N1 H6 O6 0.91(3) 1.85(3) 2.760(2) 179(3) 2_655
O3 H10 O2 0.82 1.71 2.448(2) 148.0 .
N6 H3 O6 0.86 1.92 2.772(2) 170.7 .
C8 H7 O5 0.93 2.40 3.292(3) 161.3 2_655
C1 H1 F2 0.97(3) 2.43(3) 3.391(3) 167(2) 1_665
N4 H4 N2 0.89(3) 2.12(3) 3.008(3) 176(2) .
N5 H2 O5 0.85(3) 1.96(3) 2.804(2) 176(3) 2_765
N1 H6 O6 0.91(3) 1.85(3) 2.760(2) 179(3) 2_655
O4 H11 O3 0.76(3) 2.30(3) 2.728(2) 117(3) .
O3 H10 O2 0.82 1.71 2.448(2) 148.0 .
N6 H3 O6 0.86 1.92 2.772(2) 170.7 .
C8 H7 O5 0.93 2.40 3.292(3) 161.3 2_655
C1 H1 F2 0.97(3) 2.43(3) 3.391(3) 167(2) 1_665
N4 H4 N2 0.89(3) 2.12(3) 3.008(3) 176(2) .
N5 H2 O5 0.85(3) 1.96(3) 2.804(2) 176(3) 2_765
N1 H6 O6 0.91(3) 1.85(3) 2.760(2) 179(3) 2_655
O4 H11 O3 0.76(3) 2.30(3) 2.728(2) 117(3) .

_refine_diff_density_max         0.663
_refine_diff_density_min         -0.645
_refine_diff_density_rms         0.207


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol/water (1:1)'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 1543789'
_audit_update_record             
;
2017-04-13 deposited with the CCDC.
2018-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        'flucytosine/2,6-digydroxybenzoic acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H12 F N3 O6'
_chemical_formula_weight         301.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.8713(13)
_cell_length_b                   8.4914(10)
_cell_length_c                   14.4885(18)
_cell_angle_alpha                90
_cell_angle_beta                 107.613(3)
_cell_angle_gamma                90
_cell_volume                     1274.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2113
_cell_measurement_theta_min      4.493
_cell_measurement_theta_max      64.070

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.260
_exptl_absorpt_coefficient_mu    1.204
_shelx_estimated_absorpt_T_min   0.741
_shelx_estimated_absorpt_T_max   0.731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.672
_exptl_absorpt_correction_T_max  0.741
_exptl_absorpt_process_details   '(sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  proteum2
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9444
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.493
_diffrn_reflns_theta_max         64.070
_diffrn_reflns_theta_full        64.070
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             2113
_reflns_number_gt                1957
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1269P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2065
_refine_ls_number_parameters     206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.1775
_refine_ls_wR_factor_gt          0.1707
_refine_ls_goodness_of_fit_ref   1.281
_refine_ls_restrained_S_all      1.281
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.57306(12) 1.11730(12) 0.75709(8) 0.0328(4) Uani 1 1 d . . . . .
O1 O 0.53437(12) 0.50575(14) 0.82849(9) 0.0262(4) Uani 1 1 d . . . . .
O2 O 0.64969(13) 0.20312(15) 0.57926(9) 0.0270(4) Uani 1 1 d . . . . .
O3 O 0.62624(11) 0.49154(14) 0.60611(8) 0.0219(4) Uani 1 1 d . . . . .
O4 O 0.67331(11) 0.67025(14) 0.50949(9) 0.0229(4) Uani 1 1 d . . . . .
O5 O 0.72882(12) 0.58137(15) 0.35625(9) 0.0268(4) Uani 1 1 d . . . . .
H10 H 0.7091 0.6429 0.3930 0.040 Uiso 1 1 calc R U . . .
O6 O 0.43294(12) 0.73011(16) 0.03105(9) 0.0257(4) Uani 1 1 d . . . . .
N1 N 0.62607(13) 0.89083(18) 0.63873(10) 0.0232(4) Uani 1 1 d . . . . .
H5 H 0.6423 0.8187 0.6024 0.028 Uiso 1 1 calc R U . . .
H4 H 0.6335 0.9885 0.6255 0.028 Uiso 1 1 calc R U . . .
N2 N 0.57828(13) 0.69933(17) 0.73546(11) 0.0183(4) Uani 1 1 d . . . . .
N3 N 0.51290(12) 0.76161(18) 0.86943(9) 0.0195(4) Uani 1 1 d . . . . .
H1 H 0.4879 0.7344 0.9180 0.023 Uiso 1 1 calc R U . . .
C1 C 0.56101(16) 0.9651(2) 0.77678(12) 0.0211(4) Uani 1 1 d . . . . .
C2 C 0.52250(15) 0.9173(2) 0.85222(13) 0.0215(5) Uani 1 1 d . . . . .
H2 H 0.5024 0.9914 0.8927 0.026 Uiso 1 1 calc R U . . .
C3 C 0.54092(14) 0.6456(2) 0.81355(12) 0.0197(4) Uani 1 1 d . . . . .
C4 C 0.59035(15) 0.8522(2) 0.71370(12) 0.0195(4) Uani 1 1 d . . . . .
C5 C 0.68320(15) 0.2411(2) 0.49871(12) 0.0200(4) Uani 1 1 d . . . . .
C6 C 0.71452(16) 0.1201(2) 0.44547(13) 0.0234(5) Uani 1 1 d . . . . .
H7 H 0.7105 0.0157 0.4637 0.028 Uiso 1 1 calc R U . . .
C7 C 0.75187(16) 0.1573(2) 0.36457(12) 0.0241(5) Uani 1 1 d . . . . .
H8 H 0.7748 0.0767 0.3296 0.029 Uiso 1 1 calc R U . . .
C8 C 0.75571(15) 0.3107(2) 0.33491(12) 0.0234(5) Uani 1 1 d . . . . .
H9 H 0.7797 0.3329 0.2799 0.028 Uiso 1 1 calc R U . . .
C9 C 0.72362(15) 0.4325(2) 0.38751(12) 0.0197(4) Uani 1 1 d . . . . .
C10 C 0.68796(14) 0.4001(2) 0.47216(12) 0.0177(5) Uani 1 1 d . . . . .
C11 C 0.66022(14) 0.5288(2) 0.53230(12) 0.0170(4) Uani 1 1 d . . . . .
H3 H 0.598(2) 0.623(3) 0.6969(16) 0.025(5) Uiso 1 1 d . . . . .
H11 H 0.358(3) 0.752(3) 0.0257(16) 0.039(6) Uiso 1 1 d . . . . .
H12 H 0.454(3) 0.662(4) 0.069(2) 0.049(8) Uiso 1 1 d . . . . .
H6 H 0.633(2) 0.304(3) 0.6038(18) 0.035(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.339(2) . ?
O1 C3 1.213(2) . ?
O2 C5 1.362(2) . ?
O2 H6 0.97(3) . ?
O3 C11 1.273(2) . ?
O4 C11 1.265(2) . ?
O5 C9 1.350(2) . ?
O5 H10 0.8200 . ?
O6 H11 0.81(3) . ?
O6 H12 0.79(3) . ?
N1 C4 1.301(2) . ?
N1 H5 0.8600 . ?
N1 H4 0.8600 . ?
N2 C4 1.352(2) . ?
N2 C3 1.390(2) . ?
N2 H3 0.92(2) . ?
N3 C2 1.355(3) . ?
N3 C3 1.367(2) . ?
N3 H1 0.8600 . ?
C1 C2 1.346(3) . ?
C1 C4 1.425(2) . ?
C2 H2 0.9300 . ?
C5 C6 1.387(3) . ?
C5 C10 1.410(3) . ?
C6 C7 1.388(3) . ?
C6 H7 0.9300 . ?
C7 C8 1.376(3) . ?
C7 H8 0.9300 . ?
C8 C9 1.390(3) . ?
C8 H9 0.9300 . ?
C9 C10 1.420(2) . ?
C10 C11 1.485(3) . ?

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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O2 H6 103.5(15) . . ?
C9 O5 H10 109.5 . . ?
H11 O6 H12 108(3) . . ?
C4 N1 H5 120.0 . . ?
C4 N1 H4 120.0 . . ?
H5 N1 H4 120.0 . . ?
C4 N2 C3 125.33(16) . . ?
C4 N2 H3 118.5(14) . . ?
C3 N2 H3 116.1(14) . . ?
C2 N3 C3 123.43(14) . . ?
C2 N3 H1 118.3 . . ?
C3 N3 H1 118.3 . . ?
F1 C1 C2 122.60(15) . . ?
F1 C1 C4 117.20(15) . . ?
C2 C1 C4 120.19(16) . . ?
C1 C2 N3 120.25(16) . . ?
C1 C2 H2 119.9 . . ?
N3 C2 H2 119.9 . . ?
O1 C3 N3 124.35(16) . . ?
O1 C3 N2 120.95(16) . . ?
N3 C3 N2 114.70(16) . . ?
N1 C4 N2 120.74(16) . . ?
N1 C4 C1 123.17(16) . . ?
N2 C4 C1 116.09(15) . . ?
O2 C5 C6 118.40(16) . . ?
O2 C5 C10 120.11(15) . . ?
C6 C5 C10 121.48(16) . . ?
C5 C6 C7 119.00(17) . . ?
C5 C6 H7 120.5 . . ?
C7 C6 H7 120.5 . . ?
C8 C7 C6 121.55(16) . . ?
C8 C7 H8 119.2 . . ?
C6 C7 H8 119.2 . . ?
C7 C8 C9 119.76(15) . . ?
C7 C8 H9 120.1 . . ?
C9 C8 H9 120.1 . . ?
O5 C9 C8 118.01(15) . . ?
O5 C9 C10 121.39(15) . . ?
C8 C9 C10 120.59(16) . . ?
C5 C10 C9 117.59(15) . . ?
C5 C10 C11 120.97(15) . . ?
C9 C10 C11 121.42(16) . . ?
O4 C11 O3 122.69(16) . . ?
O4 C11 C10 119.13(15) . . ?
O3 C11 C10 118.17(16) . . ?

_refine_diff_density_max         0.406
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.117


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol/water (1:1)'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3
_database_code_depnum_ccdc_archive 'CCDC 1543795'
_audit_update_record             
;
2017-04-13 deposited with the CCDC.
2018-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        'Flucytosine/glutaric acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H16 F2 N6 O6'
_chemical_formula_weight         390.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.0742(8)
_cell_length_b                   24.810(2)
_cell_length_c                   6.8938(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.058(6)
_cell_angle_gamma                90
_cell_volume                     1663.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2807
_cell_measurement_theta_min      3.563
_cell_measurement_theta_max      64.696

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    1.211
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.816
_exptl_absorpt_correction_T_max  0.865
_exptl_absorpt_process_details   '(sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  proteum2
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13900
_diffrn_reflns_av_unetI/netI     0.0915
_diffrn_reflns_av_R_equivalents  0.1010
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.563
_diffrn_reflns_theta_max         64.696
_diffrn_reflns_theta_full        64.696
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             2807
_reflns_number_gt                1936
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.2798P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2722
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0632
_refine_ls_wR_factor_ref         0.1795
_refine_ls_wR_factor_gt          0.1582
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.27995(17) 0.09615(7) 0.4812(3) 0.0307(5) Uani 1 1 d . . . . .
F2 F 0.40904(17) 0.91913(7) 0.7288(3) 0.0354(5) Uani 1 1 d . . . . .
O6 O 0.2173(2) 0.72134(9) 0.5132(3) 0.0274(6) Uani 1 1 d . . . . .
O3 O 0.07286(19) 0.29172(8) 0.2672(3) 0.0255(6) Uani 1 1 d . . . . .
O5 O 0.3410(2) 0.63080(10) 0.6341(3) 0.0305(6) Uani 1 1 d . . . . .
O2 O 0.1955(2) 0.38383(10) 0.3851(3) 0.0324(6) Uani 1 1 d . . . . .
O1 O 0.0259(2) 0.42420(9) 0.1579(4) 0.0383(7) Uani 1 1 d . . . . .
O4 O 0.1364(2) 0.59475(10) 0.4937(4) 0.0407(7) Uani 1 1 d . . . . .
N2 N 0.0511(3) 0.20095(11) 0.2460(4) 0.0240(6) Uani 1 1 d . . . . .
N6 N 0.1885(3) 0.81190(11) 0.4935(4) 0.0244(7) Uani 1 1 d . . . . .
N1 N 0.2496(2) 0.24104(10) 0.4534(4) 0.0228(6) Uani 1 1 d . . . . .
N5 N 0.3947(2) 0.77407(10) 0.6867(4) 0.0239(6) Uani 1 1 d . . . . .
N3 N 0.4201(3) 0.18585(13) 0.6390(4) 0.0269(7) Uani 1 1 d . . . . .
N4 N 0.5655(3) 0.83057(13) 0.8643(4) 0.0272(7) Uani 1 1 d . . . . .
C12 C 0.2227(3) 0.14524(13) 0.4251(5) 0.0239(7) Uani 1 1 d . . . . .
C13 C 0.2999(3) 0.19160(13) 0.5083(5) 0.0229(7) Uani 1 1 d . . . . .
C8 C 0.3578(3) 0.86908(13) 0.6692(5) 0.0254(7) Uani 1 1 d . . . . .
C5 C 0.2548(3) 0.58968(13) 0.5856(5) 0.0257(8) Uani 1 1 d . . . . .
C9 C 0.4417(3) 0.82357(13) 0.7423(5) 0.0226(7) Uani 1 1 d . . . . .
C10 C 0.1249(3) 0.24633(13) 0.3230(4) 0.0222(7) Uani 1 1 d . . . . .
C7 C 0.2336(3) 0.86284(13) 0.5458(5) 0.0258(8) Uani 1 1 d . . . . .
C11 C 0.1000(3) 0.15038(13) 0.2959(5) 0.0256(7) Uani 1 1 d . . . . .
C6 C 0.2677(3) 0.76739(13) 0.5652(4) 0.0232(7) Uani 1 1 d . . . . .
C1 C 0.1315(3) 0.42689(13) 0.2889(5) 0.0272(8) Uani 1 1 d . . . . .
C2 C 0.2077(3) 0.47843(14) 0.3593(5) 0.0304(8) Uani 1 1 d . . . . .
C3 C 0.2311(4) 0.48767(14) 0.5841(5) 0.0332(9) Uani 1 1 d . . . . .
C4 C 0.3210(4) 0.53660(14) 0.6598(6) 0.0334(9) Uani 1 1 d . . . . .
H9 H 0.178(3) 0.8916(13) 0.486(5) 0.020(8) Uiso 1 1 d . . . . .
H4 H 0.141(4) 0.3571(18) 0.345(6) 0.055(13) Uiso 1 1 d . . . . .
H6 H 0.105(4) 0.8060(14) 0.411(5) 0.032(9) Uiso 1 1 d . . . . .
H7 H 0.611(3) 0.8051(13) 0.901(4) 0.009(8) Uiso 1 1 d . . . . .
H5 H 0.301(4) 0.6595(16) 0.608(6) 0.043(12) Uiso 1 1 d . . . . .
H10 H 0.411(4) 0.5319(15) 0.637(5) 0.043(11) Uiso 1 1 d . . . . .
H13 H 0.162(3) 0.5078(14) 0.290(5) 0.027(9) Uiso 1 1 d . . . . .
H3 H -0.027(4) 0.2053(14) 0.163(5) 0.034(10) Uiso 1 1 d . . . . .
H1 H 0.447(3) 0.1533(15) 0.666(5) 0.026(9) Uiso 1 1 d . . . . .
H8 H 0.599(4) 0.8646(17) 0.909(6) 0.051(12) Uiso 1 1 d . . . . .
H2 H 0.047(3) 0.1208(14) 0.231(5) 0.020(8) Uiso 1 1 d . . . . .
H12 H 0.340(3) 0.5397(13) 0.790(6) 0.028(9) Uiso 1 1 d . . . . .
H11 H 0.297(4) 0.4764(14) 0.315(5) 0.037(10) Uiso 1 1 d . . . . .
H14 H 0.140(4) 0.4927(14) 0.622(5) 0.039(10) Uiso 1 1 d . . . . .
H15 H 0.275(4) 0.4582(15) 0.655(5) 0.039(10) Uiso 1 1 d . . . . .
H16 H 0.479(4) 0.2136(17) 0.682(5) 0.041(10) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C12 1.360(3) . ?
F2 C8 1.366(4) . ?
O6 C6 1.264(4) . ?
O3 C10 1.260(4) . ?
O5 C5 1.325(4) . ?
O5 H5 0.82(4) . ?
O2 C1 1.332(4) . ?
O2 H4 0.86(4) . ?
O1 C1 1.206(4) . ?
O4 C5 1.203(4) . ?
N2 C11 1.359(4) . ?
N2 C10 1.378(4) . ?
N2 H3 0.85(4) . ?
N6 C7 1.359(4) . ?
N6 C6 1.377(4) . ?
N6 H6 0.90(4) . ?
N1 C13 1.343(4) . ?
N1 C10 1.348(4) . ?
N5 C9 1.336(4) . ?
N5 C6 1.345(4) . ?
N3 C13 1.316(4) . ?
N3 H1 0.86(4) . ?
N3 H16 0.91(4) . ?
N4 C9 1.322(4) . ?
N4 H7 0.78(3) . ?
N4 H8 0.93(4) . ?
C12 C11 1.328(4) . ?
C12 C13 1.423(4) . ?
C8 C7 1.327(4) . ?
C8 C9 1.422(4) . ?
C5 C4 1.504(5) . ?
C7 H9 0.94(3) . ?
C11 H2 0.95(3) . ?
C1 C2 1.505(5) . ?
C2 C3 1.523(5) . ?
C2 H13 0.93(3) . ?
C2 H11 1.02(4) . ?
C3 C4 1.523(5) . ?
C3 H14 1.02(4) . ?
C3 H15 0.93(4) . ?
C4 H10 0.96(4) . ?
C4 H12 0.87(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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O5 H5 111(3) . . ?
C1 O2 H4 106(3) . . ?
C11 N2 C10 122.2(3) . . ?
C11 N2 H3 120(2) . . ?
C10 N2 H3 118(2) . . ?
C7 N6 C6 121.9(3) . . ?
C7 N6 H6 121(2) . . ?
C6 N6 H6 117(2) . . ?
C13 N1 C10 119.6(2) . . ?
C9 N5 C6 120.1(3) . . ?
C13 N3 H1 116(2) . . ?
C13 N3 H16 123(2) . . ?
H1 N3 H16 120(3) . . ?
C9 N4 H7 118(2) . . ?
C9 N4 H8 122(2) . . ?
H7 N4 H8 120(3) . . ?
C11 C12 F1 121.9(3) . . ?
C11 C12 C13 120.5(3) . . ?
F1 C12 C13 117.5(2) . . ?
N3 C13 N1 120.3(3) . . ?
N3 C13 C12 119.8(3) . . ?
N1 C13 C12 119.9(3) . . ?
C7 C8 F2 121.2(3) . . ?
C7 C8 C9 120.6(3) . . ?
F2 C8 C9 118.2(3) . . ?
O4 C5 O5 123.2(3) . . ?
O4 C5 C4 124.2(3) . . ?
O5 C5 C4 112.6(3) . . ?
N4 C9 N5 120.6(3) . . ?
N4 C9 C8 119.8(3) . . ?
N5 C9 C8 119.6(3) . . ?
O3 C10 N1 122.2(3) . . ?
O3 C10 N2 118.2(2) . . ?
N1 C10 N2 119.6(3) . . ?
C8 C7 N6 118.2(3) . . ?
C8 C7 H9 123.5(19) . . ?
N6 C7 H9 118.1(19) . . ?
C12 C11 N2 118.1(3) . . ?
C12 C11 H2 123.7(19) . . ?
N2 C11 H2 118.1(19) . . ?
O6 C6 N5 122.3(3) . . ?
O6 C6 N6 118.1(3) . . ?
N5 C6 N6 119.6(3) . . ?
O1 C1 O2 123.2(3) . . ?
O1 C1 C2 124.4(3) . . ?
O2 C1 C2 112.4(3) . . ?
C1 C2 C3 112.8(3) . . ?
C1 C2 H13 111(2) . . ?
C3 C2 H13 109(2) . . ?
C1 C2 H11 106(2) . . ?
C3 C2 H11 113.2(19) . . ?
H13 C2 H11 104(3) . . ?
C2 C3 C4 112.9(3) . . ?
C2 C3 H14 111(2) . . ?
C4 C3 H14 108(2) . . ?
C2 C3 H15 110(2) . . ?
C4 C3 H15 107(2) . . ?
H14 C3 H15 107(3) . . ?
C5 C4 C3 114.2(3) . . ?
C5 C4 H10 114(2) . . ?
C3 C4 H10 110(2) . . ?
C5 C4 H12 104(2) . . ?
C3 C4 H12 112(2) . . ?
H10 C4 H12 102(3) . . ?

_refine_diff_density_max         0.453
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.133


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Water'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1543790'
_audit_update_record             
;
2017-04-13 deposited with the CCDC.
2018-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        'Flucytosine/3,5-dihydroxybenzoic acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H20 F2 N6 O15'
_chemical_formula_weight         646.44

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'
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.298(3)
_cell_length_b                   13.507(4)
_cell_length_c                   15.536(5)
_cell_angle_alpha                109.390(8)
_cell_angle_beta                 92.328(7)
_cell_angle_gamma                103.472(7)
_cell_volume                     1393.2(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6400
_cell_measurement_theta_min      3.049
_cell_measurement_theta_max      27.485

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    0.140
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   '(sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  proteum2
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8044
_diffrn_reflns_av_unetI/netI     0.0609
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.049
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             6400
_reflns_number_gt                4628
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.3000P)²+0.5559P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6169
_refine_ls_number_parameters     410
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1072
_refine_ls_R_factor_gt           0.0919
_refine_ls_wR_factor_ref         0.3544
_refine_ls_wR_factor_gt          0.3289
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_restrained_S_all      0.943
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.4422(3) 0.54308(15) 0.87980(15) 0.0385(6) Uani 1 1 d . . . . .
F2 F 0.4986(3) -0.08509(15) 0.22279(16) 0.0419(6) Uani 1 1 d . . . . .
O15 O 0.6983(3) 0.25318(17) 0.98782(15) 0.0304(6) Uani 1 1 d . . . . .
O5 O 0.0184(4) -0.17652(18) 0.09509(18) 0.0355(6) Uani 1 1 d . . . . .
O8 O 0.3712(4) 0.08993(19) -0.03768(16) 0.0362(6) Uani 1 1 d . . . . .
H8 H 0.4524 0.1454 -0.0332 0.054 Uiso 1 1 calc R U . . .
O17 O 0.0245(4) 0.0101(2) 0.41103(18) 0.0464(7) Uani 1 1 d . . . . .
O4 O 0.7551(4) 0.44248(19) 0.95262(17) 0.0364(6) Uani 1 1 d . . . . .
H4 H 0.7308 0.3834 0.9596 0.055 Uiso 1 1 calc R U . . .
O12 O 0.5578(4) 0.3033(2) 0.47948(18) 0.0394(7) Uani 1 1 d . . . . .
O10 O 1.1546(4) 0.61561(18) 0.68360(16) 0.0318(6) Uani 1 1 d . . . . .
O9 O -0.0695(4) -0.07743(19) 0.22338(16) 0.0345(6) Uani 1 1 d . . . . .
O20 O 0.1260(4) 0.3446(2) 0.41416(19) 0.0458(7) Uani 1 1 d . . . . .
O13 O 0.3091(4) 0.15930(19) 0.60634(16) 0.0368(6) Uani 1 1 d . . . . .
O7 O 0.3057(4) 0.31113(18) 0.26296(18) 0.0426(7) Uani 1 1 d . . . . .
H7 H 0.2601 0.3077 0.3096 0.064 Uiso 1 1 calc R U . . .
O2 O 0.8131(5) 0.22531(19) 0.65013(18) 0.0443(7) Uani 1 1 d . . . . .
H2 H 0.8477 0.2305 0.6019 0.067 Uiso 1 1 calc R U . . .
O11 O 1.1687(4) 0.70509(18) 0.83311(16) 0.0356(6) Uani 1 1 d . . . . .
O16 O 0.9334(6) 0.2011(3) 0.4907(2) 0.0616(9) Uani 1 1 d . . . . .
N9 N 0.2390(4) 0.3561(2) 0.90088(19) 0.0315(7) Uani 1 1 d . . . . .
H9A H 0.1770 0.2969 0.9070 0.038 Uiso 1 1 calc R U . . .
H9B H 0.2585 0.4169 0.9458 0.038 Uiso 1 1 calc R U . . .
N8 N 0.2736(4) 0.2581(2) 0.75201(18) 0.0244(6) Uani 1 1 d . . . . .
H8A H 0.2114 0.1997 0.7595 0.029 Uiso 1 1 calc R U . . .
N5 N 0.4514(4) 0.1194(2) 0.4316(2) 0.0328(7) Uani 1 1 d . . . . .
H5 H 0.3994 0.1231 0.4809 0.039 Uiso 1 1 calc R U . . .
N10 N 0.6824(4) 0.1031(2) 0.19694(19) 0.0296(6) Uani 1 1 d . . . . .
H10A H 0.7384 0.1626 0.1895 0.036 Uiso 1 1 calc R U . . .
H10B H 0.6750 0.0416 0.1545 0.036 Uiso 1 1 calc R U . . .
N7 N 0.4299(4) 0.3429(2) 0.65814(19) 0.0292(6) Uani 1 1 d . . . . .
H7A H 0.4660 0.3401 0.6056 0.035 Uiso 1 1 calc R U . . .
C46 C 0.3344(5) 0.2023(2) 0.1141(2) 0.0273(7) Uani 1 1 d . . . . .
H46 H 0.4009 0.2648 0.1048 0.033 Uiso 1 1 calc R U . . .
C37 C 0.3041(4) 0.1013(2) 0.0454(2) 0.0240(6) Uani 1 1 d . . . . .
C17 C 0.0185(4) -0.0862(2) 0.1543(2) 0.0239(6) Uani 1 1 d . . . . .
C35 C 1.1144(4) 0.6206(2) 0.7640(2) 0.0242(6) Uani 1 1 d . . . . .
O1 O 0.6491(4) 0.4990(2) 0.44081(18) 0.0421(7) Uani 1 1 d . . . . .
C33 C 0.3370(4) 0.2491(2) 0.6684(2) 0.0251(6) Uani 1 1 d . . . . .
C38 C 0.5443(5) 0.2133(3) 0.4215(2) 0.0271(7) Uani 1 1 d . . . . .
C34 C 0.2016(4) 0.0078(2) 0.0581(2) 0.0250(6) Uani 1 1 d . . . . .
H34 H 0.1811 -0.0596 0.0116 0.030 Uiso 1 1 calc R U . . .
C22 C 0.9264(4) 0.5257(2) 0.8585(2) 0.0251(6) Uani 1 1 d . . . . .
H22 H 0.9489 0.5926 0.9059 0.030 Uiso 1 1 calc R U . . .
C30 C 0.7890(4) 0.3316(2) 0.8002(2) 0.0246(7) Uani 1 1 d . . . . .
H30 H 0.7220 0.2691 0.8093 0.030 Uiso 1 1 calc R U . . .
C40 C 0.2641(5) 0.2090(2) 0.1971(2) 0.0266(7) Uani 1 1 d . . . . .
C50 C 0.8247(4) 0.4322(2) 0.8704(2) 0.0234(6) Uani 1 1 d . . . . .
C42 C 0.4691(5) 0.4427(3) 0.7281(2) 0.0295(7) Uani 1 1 d . . . . .
H42 H 0.5364 0.5053 0.7192 0.035 Uiso 1 1 calc R U . . .
C32 C 0.3032(4) 0.3537(2) 0.8237(2) 0.0230(6) Uani 1 1 d . . . . .
C36 C 0.4087(4) 0.4472(2) 0.8083(2) 0.0256(7) Uani 1 1 d . . . . .
C24 C 0.8548(5) 0.3254(2) 0.7162(2) 0.0263(7) Uani 1 1 d . . . . .
C28 C 0.4362(5) 0.0188(3) 0.3674(3) 0.0322(8) Uani 1 1 d . . . . .
H28 H 0.3730 -0.0436 0.3778 0.039 Uiso 1 1 calc R U . . .
C44 C 0.6092(4) 0.1060(2) 0.2721(2) 0.0219(6) Uani 1 1 d . . . . .
N6 N 0.6197(4) 0.2022(2) 0.33972(18) 0.0242(6) Uani 1 1 d . . . . .
H6 H 0.6775 0.2606 0.3310 0.029 Uiso 1 1 calc R U . . .
C52 C 0.5130(5) 0.0111(2) 0.2897(2) 0.0274(7) Uani 1 1 d . . . . .
C54 C 0.1300(4) 0.0162(2) 0.1410(2) 0.0235(6) Uani 1 1 d . . . . .
C55 C 0.1605(5) 0.1172(3) 0.2112(2) 0.0264(7) Uani 1 1 d . . . . .
H55 H 0.1119 0.1226 0.2665 0.032 Uiso 1 1 calc R U . . .
C57 C 0.9949(4) 0.5187(2) 0.7749(2) 0.0225(6) Uani 1 1 d . . . . .
C56 C 0.9578(4) 0.4188(3) 0.7023(2) 0.0255(6) Uani 1 1 d . . . . .
H56 H 1.0008 0.4146 0.6460 0.031 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C36 1.359(3) . ?
F2 C52 1.346(4) . ?
O5 C17 1.260(4) . ?
O8 C37 1.373(4) . ?
O8 H8 0.8200 . ?
O4 C50 1.370(4) . ?
O4 H4 0.8200 . ?
O12 C38 1.228(4) . ?
O10 C35 1.279(4) . ?
O9 C17 1.259(4) . ?
O13 C33 1.239(4) . ?
O7 C40 1.373(4) . ?
O7 H7 0.8200 . ?
O2 C24 1.355(4) . ?
O2 H2 0.8200 . ?
O11 C35 1.246(4) . ?
N9 C32 1.298(4) . ?
N9 H9A 0.8600 . ?
N9 H9B 0.8600 . ?
N8 C32 1.360(4) . ?
N8 C33 1.373(4) . ?
N8 H8A 0.8600 . ?
N5 C38 1.355(4) . ?
N5 C28 1.369(4) . ?
N5 H5 0.8600 . ?
N10 C44 1.296(4) . ?
N10 H10A 0.8600 . ?
N10 H10B 0.8600 . ?
N7 C33 1.354(4) . ?
N7 C42 1.379(4) . ?
N7 H7A 0.8600 . ?
C46 C37 1.387(4) . ?
C46 C40 1.389(4) . ?
C46 H46 0.9300 . ?
C37 C34 1.389(4) . ?
C17 C54 1.517(4) . ?
C35 C57 1.514(4) . ?
C38 N6 1.381(4) . ?
C34 C54 1.388(4) . ?
C34 H34 0.9300 . ?
C22 C50 1.381(4) . ?
C22 C57 1.393(4) . ?
C22 H22 0.9300 . ?
C30 C50 1.390(4) . ?
C30 C24 1.393(4) . ?
C30 H30 0.9300 . ?
C40 C55 1.383(4) . ?
C42 C36 1.326(5) . ?
C42 H42 0.9300 . ?
C32 C36 1.417(4) . ?
C24 C56 1.398(4) . ?
C28 C52 1.334(5) . ?
C28 H28 0.9300 . ?
C44 N6 1.356(4) . ?
C44 C52 1.428(4) . ?
N6 H6 0.8600 . ?
C54 C55 1.397(4) . ?
C55 H55 0.9300 . ?
C57 C56 1.400(4) . ?
C56 H56 0.9300 . ?

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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C37 O8 H8 109.5 . . ?
C50 O4 H4 109.5 . . ?
C40 O7 H7 109.5 . . ?
C24 O2 H2 109.5 . . ?
C32 N9 H9A 120.0 . . ?
C32 N9 H9B 120.0 . . ?
H9A N9 H9B 120.0 . . ?
C32 N8 C33 124.0(3) . . ?
C32 N8 H8A 118.0 . . ?
C33 N8 H8A 118.0 . . ?
C38 N5 C28 123.3(3) . . ?
C38 N5 H5 118.4 . . ?
C28 N5 H5 118.4 . . ?
C44 N10 H10A 120.0 . . ?
C44 N10 H10B 120.0 . . ?
H10A N10 H10B 120.0 . . ?
C33 N7 C42 123.0(3) . . ?
C33 N7 H7A 118.5 . . ?
C42 N7 H7A 118.5 . . ?
C37 C46 C40 119.1(3) . . ?
C37 C46 H46 120.4 . . ?
C40 C46 H46 120.4 . . ?
O8 C37 C46 121.6(3) . . ?
O8 C37 C34 117.6(3) . . ?
C46 C37 C34 120.8(3) . . ?
O9 C17 O5 123.1(3) . . ?
O9 C17 C54 118.9(3) . . ?
O5 C17 C54 118.0(3) . . ?
O11 C35 O10 123.1(3) . . ?
O11 C35 C57 119.0(3) . . ?
O10 C35 C57 117.9(3) . . ?
O13 C33 N7 122.5(3) . . ?
O13 C33 N8 121.0(3) . . ?
N7 C33 N8 116.5(3) . . ?
O12 C38 N5 123.0(3) . . ?
O12 C38 N6 121.4(3) . . ?
N5 C38 N6 115.6(3) . . ?
C54 C34 C37 119.3(3) . . ?
C54 C34 H34 120.4 . . ?
C37 C34 H34 120.4 . . ?
C50 C22 C57 119.3(3) . . ?
C50 C22 H22 120.3 . . ?
C57 C22 H22 120.3 . . ?
C50 C30 C24 119.3(3) . . ?
C50 C30 H30 120.4 . . ?
C24 C30 H30 120.4 . . ?
O7 C40 C55 123.0(3) . . ?
O7 C40 C46 115.8(3) . . ?
C55 C40 C46 121.2(3) . . ?
O4 C50 C22 117.8(3) . . ?
O4 C50 C30 121.1(3) . . ?
C22 C50 C30 121.1(3) . . ?
C36 C42 N7 118.4(3) . . ?
C36 C42 H42 120.8 . . ?
N7 C42 H42 120.8 . . ?
N9 C32 N8 120.7(3) . . ?
N9 C32 C36 123.6(3) . . ?
N8 C32 C36 115.8(3) . . ?
C42 C36 F1 121.3(3) . . ?
C42 C36 C32 122.2(3) . . ?
F1 C36 C32 116.5(3) . . ?
O2 C24 C30 116.5(3) . . ?
O2 C24 C56 122.8(3) . . ?
C30 C24 C56 120.8(3) . . ?
C52 C28 N5 119.4(3) . . ?
C52 C28 H28 120.3 . . ?
N5 C28 H28 120.3 . . ?
N10 C44 N6 120.8(3) . . ?
N10 C44 C52 123.6(3) . . ?
N6 C44 C52 115.6(3) . . ?
C44 N6 C38 124.9(3) . . ?
C44 N6 H6 117.5 . . ?
C38 N6 H6 117.5 . . ?
C28 C52 F2 122.3(3) . . ?
C28 C52 C44 121.1(3) . . ?
F2 C52 C44 116.5(3) . . ?
C34 C54 C55 120.7(3) . . ?
C34 C54 C17 118.9(3) . . ?
C55 C54 C17 120.3(3) . . ?
C40 C55 C54 118.9(3) . . ?
C40 C55 H55 120.6 . . ?
C54 C55 H55 120.6 . . ?
C22 C57 C56 120.9(3) . . ?
C22 C57 C35 119.0(3) . . ?
C56 C57 C35 120.1(3) . . ?
C24 C56 C57 118.6(3) . . ?
C24 C56 H56 120.7 . . ?
C57 C56 H56 120.7 . . ?

_refine_diff_density_max         0.722
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.107


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Water'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_7
_database_code_depnum_ccdc_archive 'CCDC 1543791'
_audit_update_record             
;
2017-04-13 deposited with the CCDC.
2018-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        'Flucytosine/Gallic acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H10 F N3 O6'
_chemical_formula_weight         299.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.283(2)
_cell_length_b                   17.757(7)
_cell_length_c                   12.125(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.183(12)
_cell_angle_gamma                90
_cell_volume                     1132.8(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1908
_cell_measurement_theta_min      4.428
_cell_measurement_theta_max      64.585

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.754
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    1.355
_shelx_estimated_absorpt_T_min   0.695
_shelx_estimated_absorpt_T_max   0.728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.709
_exptl_absorpt_correction_T_max  0.713
_exptl_absorpt_process_details   '(sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  proteum2
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8580
_diffrn_reflns_av_unetI/netI     0.0841
_diffrn_reflns_av_R_equivalents  0.0706
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.428
_diffrn_reflns_theta_max         64.585
_diffrn_reflns_theta_full        64.585
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             1908
_reflns_number_gt                1625
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1182P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.040(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1861
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0564
_refine_ls_wR_factor_ref         0.1620
_refine_ls_wR_factor_gt          0.1566
_refine_ls_goodness_of_fit_ref   1.181
_refine_ls_restrained_S_all      1.181
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.8186(2) 0.56193(6) 0.00039(9) 0.0384(4) Uani 1 1 d . . . . .
O1 O 0.2112(2) 0.53191(7) 0.32294(10) 0.0342(4) Uani 1 1 d . . . . .
O2 O 0.0572(2) 0.29111(6) 0.82349(10) 0.0288(4) Uani 1 1 d . . . . .
H4 H -0.0420 0.3263 0.8117 0.043 Uiso 1 1 calc R U . . .
O3 O 0.4259(3) 0.18092(7) 0.83566(11) 0.0325(4) Uani 1 1 d . . . . .
O4 O 0.7600(2) 0.17158(6) 0.68216(10) 0.0281(4) Uani 1 1 d . . . . .
O5 O 0.5046(3) 0.37826(6) 0.40357(10) 0.0306(4) Uani 1 1 d . . . . .
O6 O 0.2241(3) 0.44275(6) 0.49130(10) 0.0339(5) Uani 1 1 d . . . . .
H6 H 0.2300 0.4704 0.4374 0.051 Uiso 1 1 calc R U . . .
N1 N 0.4060(3) 0.65175(8) 0.00859(13) 0.0323(5) Uani 1 1 d . . . . .
H10 H 0.2747 0.6803 0.0099 0.039 Uiso 1 1 calc R U . . .
H2 H 0.5043 0.6563 -0.0438 0.039 Uiso 1 1 calc R U . . .
N2 N 0.3040(3) 0.59381(8) 0.16841(12) 0.0253(4) Uani 1 1 d . . . . .
N3 N 0.5624(3) 0.49565(7) 0.24447(12) 0.0267(5) Uani 1 1 d . . . . .
H8 H 0.5934 0.4624 0.2955 0.032 Uiso 1 1 calc R U . . .
C1 C 0.3533(3) 0.54084(9) 0.24782(14) 0.0243(5) Uani 1 1 d . . . . .
C2 C 0.4566(3) 0.60087(9) 0.08718(13) 0.0242(5) Uani 1 1 d . . . . .
C3 C 0.6709(3) 0.55309(9) 0.08419(14) 0.0264(5) Uani 1 1 d . . . . .
C4 C 0.7230(3) 0.50160(9) 0.16309(15) 0.0271(5) Uani 1 1 d . . . . .
H9 H 0.8649 0.4706 0.1626 0.032 Uiso 1 1 calc R U . . .
C5 C 0.3753(3) 0.38589(9) 0.48259(14) 0.0237(5) Uani 1 1 d . . . . .
C6 C 0.3825(3) 0.33136(9) 0.57501(13) 0.0233(5) Uani 1 1 d . . . . .
C7 C 0.5681(3) 0.27608(9) 0.58422(13) 0.0240(5) Uani 1 1 d . . . . .
H7 H 0.6848 0.2721 0.5315 0.029 Uiso 1 1 calc R U . . .
C8 C 0.5778(3) 0.22682(9) 0.67279(14) 0.0224(5) Uani 1 1 d . . . . .
C9 C 0.4006(3) 0.23154(8) 0.75122(13) 0.0219(5) Uani 1 1 d . . . . .
C10 C 0.2164(3) 0.28776(9) 0.74161(13) 0.0223(5) Uani 1 1 d . . . . .
C11 C 0.2050(3) 0.33751(8) 0.65318(14) 0.0235(5) Uani 1 1 d . . . . .
H5 H 0.0803 0.3746 0.6460 0.028 Uiso 1 1 calc R U . . .
H1 H 0.770(4) 0.1572(13) 0.750(2) 0.035(5) Uiso 1 1 d . . . . .
H3 H 0.287(5) 0.1795(13) 0.869(2) 0.048(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C3 1.3448(19) . ?
O1 C1 1.2417(19) . ?
O2 C10 1.3592(18) . ?
O2 H4 0.8200 . ?
O3 C9 1.3598(19) . ?
O3 H3 0.87(3) . ?
O4 C8 1.372(2) . ?
O4 H1 0.86(2) . ?
O5 C5 1.2332(19) . ?
O6 C5 1.298(2) . ?
O6 H6 0.8200 . ?
N1 C2 1.323(2) . ?
N1 H10 0.8600 . ?
N1 H2 0.8600 . ?
N2 C2 1.334(2) . ?
N2 C1 1.354(2) . ?
N3 C4 1.362(2) . ?
N3 C1 1.369(2) . ?
N3 H8 0.8600 . ?
C2 C3 1.418(3) . ?
C3 C4 1.334(3) . ?
C4 H9 0.9300 . ?
C5 C6 1.479(2) . ?
C6 C7 1.385(2) . ?
C6 C11 1.397(2) . ?
C7 C8 1.382(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.396(2) . ?
C9 C10 1.392(2) . ?
C10 C11 1.386(2) . ?
C11 H5 0.9300 . ?

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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O2 H4 109.5 . . ?
C9 O3 H3 109.8(16) . . ?
C8 O4 H1 105.9(15) . . ?
C5 O6 H6 109.5 . . ?
C2 N1 H10 120.0 . . ?
C2 N1 H2 120.0 . . ?
H10 N1 H2 120.0 . . ?
C2 N2 C1 120.02(13) . . ?
C4 N3 C1 122.23(15) . . ?
C4 N3 H8 118.9 . . ?
C1 N3 H8 118.9 . . ?
O1 C1 N2 121.34(14) . . ?
O1 C1 N3 119.34(15) . . ?
N2 C1 N3 119.32(13) . . ?
N1 C2 N2 119.99(14) . . ?
N1 C2 C3 120.02(14) . . ?
N2 C2 C3 119.99(15) . . ?
C4 C3 F1 121.71(14) . . ?
C4 C3 C2 120.36(14) . . ?
F1 C3 C2 117.93(15) . . ?
C3 C4 N3 118.08(14) . . ?
C3 C4 H9 121.0 . . ?
N3 C4 H9 121.0 . . ?
O5 C5 O6 122.47(14) . . ?
O5 C5 C6 122.60(14) . . ?
O6 C5 C6 114.93(13) . . ?
C7 C6 C11 120.98(15) . . ?
C7 C6 C5 119.64(13) . . ?
C11 C6 C5 119.36(14) . . ?
C8 C7 C6 119.17(13) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
O4 C8 C7 119.55(12) . . ?
O4 C8 C9 119.68(14) . . ?
C7 C8 C9 120.75(15) . . ?
O3 C9 C10 123.87(13) . . ?
O3 C9 C8 116.57(14) . . ?
C10 C9 C8 119.53(14) . . ?
O2 C10 C11 123.40(14) . . ?
O2 C10 C9 116.39(13) . . ?
C11 C10 C9 120.21(13) . . ?
C10 C11 C6 119.35(15) . . ?
C10 C11 H5 120.3 . . ?
C6 C11 H5 120.3 . . ?

_refine_diff_density_max         0.480
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.121


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Water'
