# 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 2019

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1840645'
loop_
_audit_author_name
_audit_author_address
'Matheus Souza'
;Instituto de F?sica de S?o Carlos, Universidade de S?o Paulo (IFSC-USP)
Brazil
;
_audit_update_record             
;
2018-04-30 deposited with the CCDC.	2019-09-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        '5-Fluorocytosine 5-Fluorocytosinium Picrate'
_chemical_name_common            '2FCPA, Fluorocytosine, 5-FC, 5-Fluorocytosine'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 F2 N9 O9'
_chemical_formula_weight         487.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_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                   8.4380(2)
_cell_length_b                   10.6270(3)
_cell_length_c                   11.2100(3)
_cell_angle_alpha                76.3720(10)
_cell_angle_beta                 87.981(2)
_cell_angle_gamma                73.180(2)
_cell_volume                     934.53(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3568
_cell_measurement_temperature    293(2)
_cell_measurement_theta_min      3.09
_cell_measurement_theta_max      25.77

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.732
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.158
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            6873
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.088
_diffrn_reflns_theta_max         25.771
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3568
_reflns_number_gt                2253
_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       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.0828P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3568
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1279
_refine_ls_wR_factor_gt          0.1203
_refine_ls_goodness_of_fit_ref   0.894
_refine_ls_restrained_S_all      0.894
_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
F51' F 1.02662(15) 0.81787(12) 0.30663(11) 0.0680(4) Uani 1 1 d . . . . .
O21' O 0.91250(16) 0.42377(13) 0.13644(11) 0.0533(3) Uani 1 1 d . . . . .
F51 F 0.6095(2) 0.05451(14) 0.40964(12) 0.0884(5) Uani 1 1 d . . . . .
O8 O 0.62939(17) 0.38141(14) 0.99624(13) 0.0644(4) Uani 1 1 d . . . . .
O21 O 0.68315(18) 0.46879(14) 0.56855(12) 0.0618(4) Uani 1 1 d . . . . .
O3 O 0.45748(18) 0.18447(13) 0.81115(12) 0.0628(4) Uani 1 1 d . . . . .
N3 N 0.71982(19) 0.34991(15) 0.42078(13) 0.0497(4) Uani 1 1 d . . . . .
H3 H 0.768581 0.404477 0.376545 0.060 Uiso 1 1 calc R U . . .
N1' N 1.02058(18) 0.59935(15) 0.10995(14) 0.0494(4) Uani 1 1 d . . . . .
H1' H 1.054071 0.587490 0.038977 0.059 Uiso 1 1 calc R U . . .
O9 O 0.5025(2) 0.42810(15) 0.82097(14) 0.0737(5) Uani 1 1 d . . . . .
N3' N 0.88326(18) 0.53459(15) 0.28966(13) 0.0469(4) Uani 1 1 d . . . . .
O4 O 0.3099(2) -0.00425(17) 0.82329(15) 0.0791(5) Uani 1 1 d . . . . .
N9 N 0.5250(2) 0.36977(16) 0.92918(16) 0.0534(4) Uani 1 1 d . . . . .
N1 N 0.59303(19) 0.28166(16) 0.60105(14) 0.0526(4) Uani 1 1 d . . . . .
H1 H 0.557872 0.291740 0.672137 0.063 Uiso 1 1 calc R U . . .
N7 N 0.2638(2) 0.00556(16) 0.92539(17) 0.0549(4) Uani 1 1 d . . . . .
O6 O 0.1441(2) 0.12568(19) 1.32667(15) 0.0894(5) Uani 1 1 d . . . . .
N41' N 0.8563(2) 0.65329(17) 0.44024(14) 0.0590(4) Uani 1 1 d . . . . .
H41C H 0.803373 0.601276 0.483268 0.071 Uiso 1 1 calc R U . . .
H41D H 0.873679 0.717353 0.467701 0.071 Uiso 1 1 calc R U . . .
O7 O 0.2524(2) 0.28699(19) 1.32499(15) 0.0897(5) Uani 1 1 d . . . . .
N41 N 0.7520(2) 0.23626(17) 0.26594(15) 0.0594(5) Uani 1 1 d . . . . .
H41A H 0.796930 0.293927 0.222234 0.071 Uiso 1 1 calc R U . . .
H41B H 0.740075 0.170952 0.237555 0.071 Uiso 1 1 calc R U . . .
N8 N 0.2211(2) 0.2044(2) 1.27681(16) 0.0663(5) Uani 1 1 d . . . . .
O5 O 0.1862(2) -0.06676(17) 0.98318(17) 0.0955(6) Uani 1 1 d . . . . .
C2' C 0.9371(2) 0.51544(18) 0.17832(16) 0.0441(4) Uani 1 1 d . . . . .
C16 C 0.4240(2) 0.28142(17) 0.98329(16) 0.0452(4) Uani 1 1 d . . . . .
C4 C 0.7021(2) 0.24778(19) 0.37470(17) 0.0486(4) Uani 1 1 d . . . . .
C11 C 0.3980(2) 0.19001(17) 0.91354(16) 0.0451(4) Uani 1 1 d . . . . .
C12 C 0.3030(2) 0.10441(18) 0.98026(17) 0.0458(4) Uani 1 1 d . . . . .
C5' C 0.9985(2) 0.71927(18) 0.25987(18) 0.0491(5) Uani 1 1 d . . . . .
C6' C 1.0521(2) 0.70114(19) 0.15114(18) 0.0504(5) Uani 1 1 d . . . . .
H6' H 1.109920 0.756417 0.103829 0.060 Uiso 1 1 calc R U . . .
C15 C 0.3703(2) 0.28619(19) 1.09853(17) 0.0507(5) Uani 1 1 d . . . . .
H15 H 0.394016 0.345977 1.138982 0.061 Uiso 1 1 calc R U . . .
C4' C 0.9106(2) 0.63485(19) 0.33236(17) 0.0470(4) Uani 1 1 d . . . . .
C2 C 0.6655(2) 0.3732(2) 0.53351(17) 0.0498(5) Uani 1 1 d . . . . .
C13 C 0.2460(2) 0.10918(19) 1.09610(17) 0.0506(5) Uani 1 1 d . . . . .
H13 H 0.185293 0.051688 1.134903 0.061 Uiso 1 1 calc R U . . .
C14 C 0.2796(2) 0.1999(2) 1.15413(16) 0.0509(5) Uani 1 1 d . . . . .
C5 C 0.6263(3) 0.1582(2) 0.45205(18) 0.0576(5) Uani 1 1 d . . . . .
C6 C 0.5736(3) 0.1758(2) 0.56191(18) 0.0567(5) Uani 1 1 d . . . . .
H6 H 0.523689 0.115753 0.611432 0.068 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
F51' C5' 1.356(2) . ?
O21' C2' 1.246(2) . ?
F51 C5 1.342(2) . ?
O8 N9 1.2288(19) . ?
O21 C2 1.220(2) . ?
O3 C11 1.244(2) . ?
N3 C4 1.353(2) . ?
N3 C2 1.382(2) . ?
N3 H3 0.8600 . ?
N1' C6' 1.366(2) . ?
N1' C2' 1.372(2) . ?
N1' H1' 0.8600 . ?
O9 N9 1.219(2) . ?
N3' C4' 1.345(2) . ?
N3' C2' 1.353(2) . ?
O4 N7 1.214(2) . ?
N9 C16 1.461(2) . ?
N1 C6 1.352(2) . ?
N1 C2 1.363(2) . ?
N1 H1 0.8600 . ?
N7 O5 1.211(2) . ?
N7 C12 1.453(2) . ?
O6 N8 1.226(2) . ?
N41' C4' 1.316(2) . ?
N41' H41C 0.8600 . ?
N41' H41D 0.8600 . ?
O7 N8 1.225(2) . ?
N41 C4 1.297(2) . ?
N41 H41A 0.8600 . ?
N41 H41B 0.8600 . ?
N8 C14 1.452(2) . ?
C16 C15 1.361(2) . ?
C16 C11 1.448(2) . ?
C4 C5 1.411(3) . ?
C11 C12 1.445(3) . ?
C12 C13 1.376(2) . ?
C5' C6' 1.322(3) . ?
C5' C4' 1.419(3) . ?
C6' H6' 0.9300 . ?
C15 C14 1.386(3) . ?
C15 H15 0.9300 . ?
C13 C14 1.378(3) . ?
C13 H13 0.9300 . ?
C5 C6 1.331(3) . ?
C6 H6 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
C4 N3 C2 124.95(15) . . ?
C4 N3 H3 117.5 . . ?
C2 N3 H3 117.5 . . ?
C6' N1' C2' 122.02(16) . . ?
C6' N1' H1' 119.0 . . ?
C2' N1' H1' 119.0 . . ?
C4' N3' C2' 120.42(15) . . ?
O9 N9 O8 123.17(16) . . ?
O9 N9 C16 119.18(16) . . ?
O8 N9 C16 117.65(16) . . ?
C6 N1 C2 123.31(17) . . ?
C6 N1 H1 118.3 . . ?
C2 N1 H1 118.3 . . ?
O5 N7 O4 120.97(17) . . ?
O5 N7 C12 119.12(18) . . ?
O4 N7 C12 119.91(16) . . ?
C4' N41' H41C 120.0 . . ?
C4' N41' H41D 120.0 . . ?
H41C N41' H41D 120.0 . . ?
C4 N41 H41A 120.0 . . ?
C4 N41 H41B 120.0 . . ?
H41A N41 H41B 120.0 . . ?
O7 N8 O6 123.60(18) . . ?
O7 N8 C14 117.71(19) . . ?
O6 N8 C14 118.7(2) . . ?
O21' C2' N3' 121.64(15) . . ?
O21' C2' N1' 119.29(15) . . ?
N3' C2' N1' 119.07(16) . . ?
C15 C16 C11 125.28(16) . . ?
C15 C16 N9 117.09(16) . . ?
C11 C16 N9 117.51(15) . . ?
N41 C4 N3 120.77(16) . . ?
N41 C4 C5 123.64(17) . . ?
N3 C4 C5 115.59(16) . . ?
O3 C11 C12 125.53(17) . . ?
O3 C11 C16 122.80(16) . . ?
C12 C11 C16 111.61(16) . . ?
C13 C12 C11 123.83(16) . . ?
C13 C12 N7 116.26(16) . . ?
C11 C12 N7 119.91(16) . . ?
C6' C5' F51' 121.47(16) . . ?
C6' C5' C4' 120.89(17) . . ?
F51' C5' C4' 117.64(16) . . ?
C5' C6' N1' 118.44(17) . . ?
C5' C6' H6' 120.8 . . ?
N1' C6' H6' 120.8 . . ?
C16 C15 C14 118.42(17) . . ?
C16 C15 H15 120.8 . . ?
C14 C15 H15 120.8 . . ?
N41' C4' N3' 119.86(17) . . ?
N41' C4' C5' 120.98(17) . . ?
N3' C4' C5' 119.16(16) . . ?
O21 C2 N1 123.45(17) . . ?
O21 C2 N3 121.52(16) . . ?
N1 C2 N3 115.03(17) . . ?
C12 C13 C14 119.43(17) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C13 C14 C15 121.41(17) . . ?
C13 C14 N8 119.63(18) . . ?
C15 C14 N8 118.95(18) . . ?
C6 C5 F51 121.52(17) . . ?
C6 C5 C4 121.54(17) . . ?
F51 C5 C4 116.95(17) . . ?
C5 C6 N1 119.57(17) . . ?
C5 C6 H6 120.2 . . ?
N1 C6 H6 120.2 . . ?

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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4' N3' C2' O21' -179.60(16) . . . . ?
C4' N3' C2' N1' 0.3(3) . . . . ?
C6' N1' C2' O21' -179.65(16) . . . . ?
C6' N1' C2' N3' 0.5(3) . . . . ?
O9 N9 C16 C15 -139.49(18) . . . . ?
O8 N9 C16 C15 40.5(2) . . . . ?
O9 N9 C16 C11 44.3(2) . . . . ?
O8 N9 C16 C11 -135.69(17) . . . . ?
C2 N3 C4 N41 177.65(17) . . . . ?
C2 N3 C4 C5 -2.0(3) . . . . ?
C15 C16 C11 O3 -175.87(18) . . . . ?
N9 C16 C11 O3 -0.1(3) . . . . ?
C15 C16 C11 C12 1.4(3) . . . . ?
N9 C16 C11 C12 177.20(15) . . . . ?
O3 C11 C12 C13 176.71(17) . . . . ?
C16 C11 C12 C13 -0.5(3) . . . . ?
O3 C11 C12 N7 -2.9(3) . . . . ?
C16 C11 C12 N7 179.97(15) . . . . ?
O5 N7 C12 C13 -0.7(3) . . . . ?
O4 N7 C12 C13 179.90(17) . . . . ?
O5 N7 C12 C11 178.93(18) . . . . ?
O4 N7 C12 C11 -0.5(3) . . . . ?
F51' C5' C6' N1' 179.54(16) . . . . ?
C4' C5' C6' N1' 0.1(3) . . . . ?
C2' N1' C6' C5' -0.7(3) . . . . ?
C11 C16 C15 C14 -1.8(3) . . . . ?
N9 C16 C15 C14 -177.58(16) . . . . ?
C2' N3' C4' N41' 179.35(16) . . . . ?
C2' N3' C4' C5' -0.8(3) . . . . ?
C6' C5' C4' N41' -179.55(17) . . . . ?
F51' C5' C4' N41' 1.0(3) . . . . ?
C6' C5' C4' N3' 0.6(3) . . . . ?
F51' C5' C4' N3' -178.84(15) . . . . ?
C6 N1 C2 O21 179.95(18) . . . . ?
C6 N1 C2 N3 -0.4(3) . . . . ?
C4 N3 C2 O21 -178.72(18) . . . . ?
C4 N3 C2 N1 1.6(3) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
N7 C12 C13 C14 179.56(16) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C12 C13 C14 N8 -179.41(16) . . . . ?
C16 C15 C14 C13 1.1(3) . . . . ?
C16 C15 C14 N8 -179.74(16) . . . . ?
O7 N8 C14 C13 -179.49(18) . . . . ?
O6 N8 C14 C13 0.8(3) . . . . ?
O7 N8 C14 C15 1.4(3) . . . . ?
O6 N8 C14 C15 -178.37(18) . . . . ?
N41 C4 C5 C6 -178.4(2) . . . . ?
N3 C4 C5 C6 1.2(3) . . . . ?
N41 C4 C5 F51 1.4(3) . . . . ?
N3 C4 C5 F51 -178.94(17) . . . . ?
F51 C5 C6 N1 180.00(18) . . . . ?
C4 C5 C6 N1 -0.2(3) . . . . ?
C2 N1 C6 C5 -0.3(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
_geom_hbond_publ_flag
N3 H3 N3' 0.86 1.97 2.825(2) 174.5 . yes
N1' H1' O21' 0.86 2.00 2.8527(19) 169.3 2_765 yes
N1 H1 O3 0.86 2.02 2.696(2) 135.0 . yes
N1 H1 O9 0.86 2.41 3.173(2) 148.7 . yes
N41' H41C O21 0.86 2.01 2.869(2) 173.6 . yes
N41 H41A O21' 0.86 1.97 2.8237(19) 174.5 . yes
N41 H41B O4 0.86 2.19 3.049(2) 174.6 2_656 yes
C6' H6' O8 0.93 2.64 3.119(2) 112.5 2_766 yes
C6' H6' O5 0.93 2.28 3.191(2) 165.1 1_664 yes
C6 H6 F51 0.93 2.45 3.204(2) 138.5 2_656 yes

_refine_diff_density_max         0.362
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.060

_vrf_PLAT430_shelxl              
;
PROBLEM: Short Inter D...A Contact O8       ..O8        .       2.83 Ang.  
RESPONSE: Unusual Short interatomic distance due to dipolo-dipole intermolecular
interaction between nitro groups
;

####################################################################### 
# 
# 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_10540sadabs
_database_code_depnum_ccdc_archive 'CCDC 1840646'
loop_
_audit_author_name
_audit_author_address
'Matheus Souza'
;Instituto de F?sica de S?o Carlos, Universidade de S?o Paulo (IFSC-USP)
Brazil
;
_audit_update_record             
;
2018-04-30 deposited with the CCDC.	2019-09-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
'5-Fluorocytosinium 3,5-dinitrosalicylate monohydrate'
_chemical_name_common            '5-FC, 5-Fluorocytosine, Fluorocytosine, FCDNS'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H10 F N5 O9'
_chemical_formula_weight         375.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   21.337(3)
_cell_length_b                   5.4905(9)
_cell_length_c                   12.445(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.196(3)
_cell_angle_gamma                90
_cell_volume                     1419.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9555
_cell_measurement_theta_max      31.22
_cell_measurement_theta_min      2.86

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.031
_exptl_absorpt_coefficient_mu    0.162
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21278
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.681
_diffrn_reflns_theta_max         31.228
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             4532
_reflns_number_gt                4299
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.808
_reflns_Friedel_fraction_max     0.973
_reflns_Friedel_fraction_full    0.973

_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       'Bruker APEX2 software'
_computing_cell_refinement       'SAINT V7.68A integration software'
_computing_data_reduction        ?
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.0510P)²+0.3772P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1838 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4532
_refine_ls_number_parameters     239
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0832
_refine_ls_wR_factor_gt          0.0808
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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
F51 F 0.25310(5) -0.1249(2) 0.36718(8) 0.0162(2) Uani 1 1 d . . . . .
N3 N 0.19015(6) 0.4140(3) 0.22111(10) 0.0098(2) Uani 1 1 d . . . . .
H3 H 0.166739 0.537234 0.228969 0.012 Uiso 1 1 calc R U . . .
O4 O 0.34957(6) 0.5509(2) 0.26177(10) 0.0148(2) Uani 1 1 d . . . . .
H4 H 0.338136 0.554037 0.320343 0.022 Uiso 1 1 calc R U . . .
C9 C 0.38849(7) 0.3659(3) 0.26171(12) 0.0100(3) Uani 1 1 d . . . . .
C12 C 0.47039(7) -0.0345(3) 0.26808(13) 0.0115(3) Uani 1 1 d . . . . .
O2 O 0.39550(6) 0.1410(2) 0.54032(9) 0.0153(2) Uani 1 1 d . . . . .
C8 C 0.40547(7) 0.2134(3) 0.35703(12) 0.0095(3) Uani 1 1 d . . . . .
N41 N 0.17720(6) 0.2678(3) 0.38944(10) 0.0122(2) Uani 1 1 d . . . . .
H41A H 0.153973 0.392505 0.396062 0.015 Uiso 1 1 calc R U . . .
H41B H 0.184667 0.158390 0.440211 0.015 Uiso 1 1 calc R U . . .
C13 C 0.44568(7) 0.0156(3) 0.35979(12) 0.0106(3) Uani 1 1 d . . . . .
H13 H 0.456102 -0.082815 0.422153 0.013 Uiso 1 1 calc R U . . .
O8 O 0.52610(6) -0.3659(3) 0.35602(11) 0.0190(3) Uani 1 1 d . . . . .
O3 O 0.33885(6) 0.4462(2) 0.44576(10) 0.0164(2) Uani 1 1 d . . . . .
C4 C 0.20116(6) 0.2446(3) 0.30211(11) 0.0093(3) Uani 1 1 d . . . . .
C11 C 0.45555(7) 0.1060(3) 0.17379(12) 0.0123(3) Uani 1 1 d . . . . .
H11 H 0.472554 0.068384 0.113337 0.015 Uiso 1 1 calc R U . . .
O21 O 0.20252(6) 0.5687(2) 0.05876(9) 0.0136(2) Uani 1 1 d . . . . .
O7 O 0.53324(7) -0.2870(3) 0.18835(11) 0.0239(3) Uani 1 1 d . . . . .
C5 C 0.24017(7) 0.0430(3) 0.28666(12) 0.0107(3) Uani 1 1 d . . . . .
N1 N 0.24911(6) 0.2020(3) 0.11640(10) 0.0109(2) Uani 1 1 d . . . . .
H1 H 0.263611 0.186052 0.057722 0.013 Uiso 1 1 calc R U . . .
C7 C 0.37875(7) 0.2675(3) 0.45635(12) 0.0115(3) Uani 1 1 d . . . . .
N5 N 0.51298(6) -0.2425(3) 0.27165(12) 0.0147(3) Uani 1 1 d . . . . .
C10 C 0.41499(7) 0.3035(3) 0.17057(12) 0.0112(3) Uani 1 1 d . . . . .
N4 N 0.40126(6) 0.4462(3) 0.06829(11) 0.0148(3) Uani 1 1 d . . . . .
OW O 0.11033(6) 0.7705(3) 0.24873(10) 0.0187(3) Uani 1 1 d G . . . .
HWA H 0.100378 0.775463 0.305101 0.028 Uiso 1 1 d G U . . .
HWB H 0.086967 0.869420 0.207349 0.028 Uiso 1 1 d G U . . .
C6 C 0.26268(7) 0.0239(3) 0.19460(12) 0.0113(3) Uani 1 1 d . . . . .
H6 H 0.287363 -0.109920 0.184313 0.014 Uiso 1 1 calc R U . . .
O6 O 0.42575(7) 0.3802(3) -0.00671(10) 0.0248(3) Uani 1 1 d . . . . .
O5 O 0.36637(7) 0.6253(3) 0.06229(12) 0.0294(3) Uani 1 1 d . . . . .
C2 C 0.21380(7) 0.4036(3) 0.12644(11) 0.0097(3) Uani 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
F51 C5 1.3432(18) . ?
N3 C4 1.3520(19) . ?
N3 C2 1.3847(17) . ?
N3 H3 0.8600 . ?
O4 C9 1.3124(19) . ?
O4 H4 0.8200 . ?
C9 C10 1.4199(19) . ?
C9 C8 1.429(2) . ?
C12 C11 1.379(2) . ?
C12 C13 1.390(2) . ?
C12 N5 1.454(2) . ?
O2 C7 1.238(2) . ?
C8 C13 1.379(2) . ?
C8 C7 1.5043(19) . ?
N41 C4 1.3087(18) . ?
N41 H41A 0.8600 . ?
N41 H41B 0.8600 . ?
C13 H13 0.9300 . ?
O8 N5 1.227(2) . ?
O3 C7 1.286(2) . ?
C4 C5 1.424(2) . ?
C11 C10 1.383(2) . ?
C11 H11 0.9300 . ?
O21 C2 1.2235(19) . ?
O7 N5 1.2352(18) . ?
C5 C6 1.3435(19) . ?
N1 C2 1.361(2) . ?
N1 C6 1.363(2) . ?
N1 H1 0.8600 . ?
C10 N4 1.466(2) . ?
N4 O6 1.2240(19) . ?
N4 O5 1.226(2) . ?
OW HWA 0.7785 . ?
OW HWB 0.8316 . ?
C6 H6 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
C4 N3 C2 124.83(13) . . ?
C4 N3 H3 117.6 . . ?
C2 N3 H3 117.6 . . ?
C9 O4 H4 109.5 . . ?
O4 C9 C10 123.68(13) . . ?
O4 C9 C8 119.57(12) . . ?
C10 C9 C8 116.74(13) . . ?
C11 C12 C13 122.10(14) . . ?
C11 C12 N5 119.07(13) . . ?
C13 C12 N5 118.83(14) . . ?
C13 C8 C9 121.34(13) . . ?
C13 C8 C7 119.03(13) . . ?
C9 C8 C7 119.63(13) . . ?
C4 N41 H41A 120.0 . . ?
C4 N41 H41B 120.0 . . ?
H41A N41 H41B 120.0 . . ?
C8 C13 C12 119.07(14) . . ?
C8 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
N41 C4 N3 121.19(14) . . ?
N41 C4 C5 122.63(14) . . ?
N3 C4 C5 116.18(12) . . ?
C12 C11 C10 118.95(13) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
F51 C5 C6 122.01(14) . . ?
F51 C5 C4 117.36(12) . . ?
C6 C5 C4 120.63(14) . . ?
C2 N1 C6 123.33(12) . . ?
C2 N1 H1 118.3 . . ?
C6 N1 H1 118.3 . . ?
O2 C7 O3 124.87(14) . . ?
O2 C7 C8 119.49(14) . . ?
O3 C7 C8 115.64(13) . . ?
O8 N5 O7 123.64(15) . . ?
O8 N5 C12 118.60(13) . . ?
O7 N5 C12 117.76(14) . . ?
C11 C10 C9 121.79(14) . . ?
C11 C10 N4 116.36(13) . . ?
C9 C10 N4 121.85(14) . . ?
O6 N4 O5 123.38(15) . . ?
O6 N4 C10 117.93(15) . . ?
O5 N4 C10 118.68(13) . . ?
HWA OW HWB 106.7 . . ?
C5 C6 N1 119.61(14) . . ?
C5 C6 H6 120.2 . . ?
N1 C6 H6 120.2 . . ?
O21 C2 N1 124.45(13) . . ?
O21 C2 N3 120.17(14) . . ?
N1 C2 N3 115.37(13) . . ?

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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 C9 C8 C13 179.30(14) . . . . ?
C10 C9 C8 C13 0.0(2) . . . . ?
O4 C9 C8 C7 -0.2(2) . . . . ?
C10 C9 C8 C7 -179.53(13) . . . . ?
C9 C8 C13 C12 0.5(2) . . . . ?
C7 C8 C13 C12 180.00(13) . . . . ?
C11 C12 C13 C8 -0.6(2) . . . . ?
N5 C12 C13 C8 179.71(14) . . . . ?
C2 N3 C4 N41 179.82(14) . . . . ?
C2 N3 C4 C5 0.1(2) . . . . ?
C13 C12 C11 C10 0.3(2) . . . . ?
N5 C12 C11 C10 179.94(14) . . . . ?
N41 C4 C5 F51 -1.3(2) . . . . ?
N3 C4 C5 F51 178.46(13) . . . . ?
N41 C4 C5 C6 178.60(15) . . . . ?
N3 C4 C5 C6 -1.7(2) . . . . ?
C13 C8 C7 O2 3.3(2) . . . . ?
C9 C8 C7 O2 -177.18(14) . . . . ?
C13 C8 C7 O3 -176.29(13) . . . . ?
C9 C8 C7 O3 3.3(2) . . . . ?
C11 C12 N5 O8 179.73(14) . . . . ?
C13 C12 N5 O8 -0.6(2) . . . . ?
C11 C12 N5 O7 -1.3(2) . . . . ?
C13 C12 N5 O7 178.40(15) . . . . ?
C12 C11 C10 C9 0.2(2) . . . . ?
C12 C11 C10 N4 179.77(14) . . . . ?
O4 C9 C10 C11 -179.62(15) . . . . ?
C8 C9 C10 C11 -0.4(2) . . . . ?
O4 C9 C10 N4 0.9(2) . . . . ?
C8 C9 C10 N4 -179.88(13) . . . . ?
C11 C10 N4 O6 0.7(2) . . . . ?
C9 C10 N4 O6 -179.74(14) . . . . ?
C11 C10 N4 O5 -178.84(15) . . . . ?
C9 C10 N4 O5 0.7(2) . . . . ?
F51 C5 C6 N1 -178.76(13) . . . . ?
C4 C5 C6 N1 1.4(2) . . . . ?
C2 N1 C6 C5 0.6(2) . . . . ?
C6 N1 C2 O21 177.90(14) . . . . ?
C6 N1 C2 N3 -2.0(2) . . . . ?
C4 N3 C2 O21 -178.25(14) . . . . ?
C4 N3 C2 N1 1.7(2) . . . . ?

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
_geom_hbond_publ_flag
N3 H3 OW 0.86 1.81 2.6680(18) 173.1 . yes
O4 H4 O3 0.82 1.67 2.4218(17) 152.2 . yes
N41 H41A O2 0.86 2.00 2.8260(18) 161.9 4_556 yes
N41 H41B O3 0.86 1.99 2.7863(18) 154.1 4_546 yes
N1 H1 O21 0.86 1.88 2.7164(16) 165.5 4_545 yes
C6 H6 O4 0.93 2.36 3.190(2) 148.3 1_545 yes

_refine_diff_density_max         0.338
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.051

