# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_5FC-GEA_FI
_database_code_depnum_ccdc_archive 'CCDC 1578356'
loop_
_audit_author_name
_audit_author_address
'Sunil Kumar Nechipadappu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'FLUCYTOSINE-GENTISIC ACID form I'
_chemical_name_common            'FLUCYTOSINE-GENTISIC ACID form I'
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H6 O4, C4 H4 F N3 O'
_chemical_formula_sum            'C11 H10 F N3 O5'
_chemical_formula_weight         283.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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           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                   5.455(15)
_cell_length_b                   14.57(4)
_cell_length_c                   14.53(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.13(4)
_cell_angle_gamma                90
_cell_volume                     1148(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    2706
_cell_measurement_theta_min      3.132
_cell_measurement_theta_max      28.018

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.141
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.695
_exptl_absorpt_correction_T_max  0.750
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            5255
_diffrn_reflns_av_unetI/netI     0.0695
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.132
_diffrn_reflns_theta_max         28.018
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             2706
_reflns_number_gt                1667
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1186P)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         2706
_refine_ls_number_parameters     205
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1078
_refine_ls_R_factor_gt           0.0732
_refine_ls_wR_factor_ref         0.2095
_refine_ls_wR_factor_gt          0.1819
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_restrained_S_all      0.992
_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
C1 C -0.2251(5) 1.30945(17) 0.33416(18) 0.0422(6) Uani 1 1 d . . . . .
C2 C 0.0143(5) 1.30200(17) 0.37939(19) 0.0432(6) Uani 1 1 d . . . . .
C3 C 0.1080(5) 1.22017(18) 0.39860(19) 0.0459(6) Uani 1 1 d . . . . .
H3A H 0.265939 1.214071 0.429097 0.055 Uiso 1 1 calc R U . . .
C4 C -0.2589(4) 1.15324(17) 0.32974(18) 0.0435(6) Uani 1 1 d . . . . .
F1 F 0.1393(3) 1.37864(11) 0.40185(12) 0.0620(5) Uani 1 1 d . . . . .
N3 N -0.3215(5) 1.38948(18) 0.3138(2) 0.0587(7) Uani 1 1 d . . . . .
N2 N -0.3543(4) 1.23515(14) 0.31132(16) 0.0445(6) Uani 1 1 d . . . . .
H2N H -0.478(7) 1.391(2) 0.284(3) 0.085(11) Uiso 1 1 d . . . . .
H3N H -0.246(5) 1.440(2) 0.324(2) 0.053(8) Uiso 1 1 d . . . . .
N1 N -0.0272(4) 1.14579(16) 0.37362(16) 0.0440(6) Uani 1 1 d . . . . .
H1N H 0.032(5) 1.090(2) 0.3781(19) 0.047(7) Uiso 1 1 d . . . . .
O1 O -0.3766(3) 1.08218(12) 0.30787(14) 0.0545(6) Uani 1 1 d . . . . .
C5 C -0.0221(5) 0.90193(17) 0.36863(18) 0.0422(6) Uani 1 1 d . . . . .
C6 C 0.0381(4) 0.80574(17) 0.37836(17) 0.0382(6) Uani 1 1 d . . . . .
C7 C -0.1221(5) 0.73821(16) 0.34136(18) 0.0423(6) Uani 1 1 d . . . . .
H7 H -0.272560 0.754984 0.309671 0.051 Uiso 1 1 calc R U . . .
C8 C -0.0630(5) 0.64826(18) 0.35060(19) 0.0459(6) Uani 1 1 d . . . . .
C9 C 0.1599(5) 0.62319(19) 0.39797(19) 0.0495(7) Uani 1 1 d . . . . .
H9 H 0.201331 0.561437 0.404354 0.059 Uiso 1 1 calc R U . . .
C10 C 0.3178(5) 0.68780(19) 0.43504(19) 0.0479(7) Uani 1 1 d . . . . .
H10 H 0.466979 0.669983 0.467047 0.057 Uiso 1 1 calc R U . . .
C11 C 0.2616(5) 0.77970(18) 0.42622(18) 0.0425(6) Uani 1 1 d . . . . .
O2 O 0.1108(4) 0.96216(12) 0.40510(14) 0.0561(6) Uani 1 1 d . . . . .
O3 O -0.2248(3) 0.92143(13) 0.31791(14) 0.0565(6) Uani 1 1 d D . . . .
H3O H -0.263(6) 0.9837(12) 0.316(2) 0.066(9) Uiso 1 1 d D . . . .
O4 O 0.4257(3) 0.84052(14) 0.46537(14) 0.0542(5) Uani 1 1 d . . . . .
H4O H 0.364(7) 0.901(2) 0.454(2) 0.076(10) Uiso 1 1 d . . . . .
O5 O -0.2110(4) 0.57964(13) 0.31572(17) 0.0626(7) Uani 1 1 d . . . . .
H5O H -0.330(7) 0.598(3) 0.283(3) 0.095(14) 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
C1 N3 1.300(5) . ?
C1 N2 1.315(4) . ?
C1 C2 1.402(5) . ?
C2 C3 1.315(5) . ?
C2 F1 1.331(4) . ?
C3 N1 1.339(4) . ?
C3 H3A 0.9300 . ?
C4 O1 1.242(4) . ?
C4 N2 1.318(4) . ?
C4 N1 1.358(5) . ?
N3 H2N 0.91(4) . ?
N3 H3N 0.84(3) . ?
N1 H1N 0.88(3) . ?
C5 O2 1.222(4) . ?
C5 O3 1.293(4) . ?
C5 C6 1.443(5) . ?
C6 C7 1.386(4) . ?
C6 C11 1.390(5) . ?
C7 C8 1.353(5) . ?
C7 H7 0.9300 . ?
C8 O5 1.349(4) . ?
C8 C9 1.381(5) . ?
C9 C10 1.349(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.377(5) . ?
C10 H10 0.9300 . ?
C11 O4 1.342(4) . ?
O3 H3O 0.930(17) . ?
O4 H4O 0.95(4) . ?
O5 H5O 0.81(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
N3 C1 N2 119.2(3) . . ?
N3 C1 C2 120.7(3) . . ?
N2 C1 C2 120.1(3) . . ?
C3 C2 F1 122.1(3) . . ?
C3 C2 C1 119.4(3) . . ?
F1 C2 C1 118.5(2) . . ?
C2 C3 N1 119.1(3) . . ?
C2 C3 H3A 120.5 . . ?
N1 C3 H3A 120.5 . . ?
O1 C4 N2 121.4(3) . . ?
O1 C4 N1 118.9(3) . . ?
N2 C4 N1 119.7(2) . . ?
C1 N3 H2N 118(2) . . ?
C1 N3 H3N 124(2) . . ?
H2N N3 H3N 118(3) . . ?
C1 N2 C4 120.3(3) . . ?
C3 N1 C4 121.4(3) . . ?
C3 N1 H1N 123.2(19) . . ?
C4 N1 H1N 115.1(19) . . ?
O2 C5 O3 121.4(3) . . ?
O2 C5 C6 122.4(3) . . ?
O3 C5 C6 116.2(2) . . ?
C7 C6 C11 118.9(3) . . ?
C7 C6 C5 121.6(3) . . ?
C11 C6 C5 119.5(2) . . ?
C8 C7 C6 121.0(3) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
O5 C8 C7 123.6(3) . . ?
O5 C8 C9 116.8(3) . . ?
C7 C8 C9 119.6(3) . . ?
C10 C9 C8 120.4(3) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 121.0(3) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
O4 C11 C10 118.1(3) . . ?
O4 C11 C6 122.8(3) . . ?
C10 C11 C6 119.1(2) . . ?
C5 O3 H3O 114(2) . . ?
C11 O4 H4O 109(2) . . ?
C8 O5 H5O 112(3) . . ?

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
N3 C1 C2 C3 -179.5(3) . . . . ?
N2 C1 C2 C3 0.1(4) . . . . ?
N3 C1 C2 F1 0.7(4) . . . . ?
N2 C1 C2 F1 -179.7(2) . . . . ?
F1 C2 C3 N1 -179.6(2) . . . . ?
C1 C2 C3 N1 0.6(4) . . . . ?
N3 C1 N2 C4 178.8(3) . . . . ?
C2 C1 N2 C4 -0.8(4) . . . . ?
O1 C4 N2 C1 -179.2(2) . . . . ?
N1 C4 N2 C1 0.8(4) . . . . ?
C2 C3 N1 C4 -0.6(4) . . . . ?
O1 C4 N1 C3 179.9(2) . . . . ?
N2 C4 N1 C3 -0.2(4) . . . . ?
O2 C5 C6 C7 175.9(2) . . . . ?
O3 C5 C6 C7 -4.9(4) . . . . ?
O2 C5 C6 C11 -3.9(4) . . . . ?
O3 C5 C6 C11 175.4(2) . . . . ?
C11 C6 C7 C8 -0.5(4) . . . . ?
C5 C6 C7 C8 179.7(2) . . . . ?
C6 C7 C8 O5 -179.7(2) . . . . ?
C6 C7 C8 C9 0.3(4) . . . . ?
O5 C8 C9 C10 -179.9(3) . . . . ?
C7 C8 C9 C10 0.1(4) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C9 C10 C11 O4 179.4(2) . . . . ?
C9 C10 C11 C6 0.1(4) . . . . ?
C7 C6 C11 O4 -179.0(2) . . . . ?
C5 C6 C11 O4 0.8(4) . . . . ?
C7 C6 C11 C10 0.3(4) . . . . ?
C5 C6 C11 C10 -179.9(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
C3 H3A O4 0.93 2.29 3.176(7) 158.0 3_676 yes
N3 H2N O3 0.91(4) 2.12(4) 2.999(7) 159(3) 2_455 yes
N3 H3N O5 0.84(3) 2.05(3) 2.835(8) 154(3) 1_565 yes
N1 H1N O2 0.88(3) 1.94(3) 2.804(8) 168(2) . yes
C7 H7 N2 0.93 2.56 3.425(8) 154.9 2_445 yes
O3 H3O O1 0.930(17) 1.564(19) 2.483(7) 169(3) . yes
O4 H4O O2 0.95(4) 1.74(4) 2.557(5) 143(3) . yes
O5 H5O O1 0.81(4) 1.97(4) 2.725(6) 153(4) 2_445 yes

_refine_diff_density_max         0.264
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.072



_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_5FC-GEA_FII
_database_code_depnum_ccdc_archive 'CCDC 2245529'
loop_
_audit_author_name
_audit_author_address
'Sunil Kumar Nechipadappu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'FLUCYTOSINE-GENTISIC ACID form II'
_chemical_name_common            'FLUCYTOSINE-GENTISIC ACID form II'
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H6 O4, C4 H4 F N3 O'
_chemical_formula_sum            'C11 H10 F N3 O5'
_chemical_formula_weight         283.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      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                   3.715(2)
_cell_length_b                   14.634(8)
_cell_length_c                   22.239(15)
_cell_angle_alpha                90
_cell_angle_beta                 92.71(2)
_cell_angle_gamma                90
_cell_volume                     1207.8(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    3208
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      25.2

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.134
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6470
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            14777
_diffrn_reflns_av_unetI/netI     0.0757
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.302
_diffrn_reflns_theta_max         30.553
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3691
_reflns_number_gt                2048
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0375P)²+0.2689P] 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         3691
_refine_ls_number_parameters     205
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1158
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1249
_refine_ls_wR_factor_gt          0.1027
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.018
_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
C1 C 0.6807(4) 0.80561(11) 0.45971(8) 0.0301(4) Uani 1 1 d . . . . .
C2 C 0.4613(5) 0.74377(11) 0.55035(8) 0.0336(4) Uani 1 1 d . . . . .
H2 H 0.355976 0.696043 0.570809 0.040 Uiso 1 1 calc R U . . .
C3 C 0.5526(4) 0.82098(11) 0.57855(8) 0.0314(4) Uani 1 1 d . . . . .
C4 C 0.7233(4) 0.89290(11) 0.54724(8) 0.0284(4) Uani 1 1 d . . . . .
F1 F 0.4949(3) 0.83340(7) 0.63779(5) 0.0503(3) Uani 1 1 d . . . . .
N1 N 0.5255(4) 0.73618(10) 0.49085(7) 0.0336(4) Uani 1 1 d . . . . .
H1N H 0.464(5) 0.6824(15) 0.4675(9) 0.058(6) Uiso 1 1 d . . . . .
N2 N 0.7856(4) 0.88273(9) 0.48848(6) 0.0293(3) Uani 1 1 d . . . . .
N3 N 0.8246(4) 0.96836(10) 0.57533(8) 0.0374(4) Uani 1 1 d . . . . .
H2N H 0.933(5) 1.0130(15) 0.5535(10) 0.058(6) Uiso 1 1 d . . . . .
H3N H 0.758(5) 0.9765(13) 0.6114(9) 0.048(6) Uiso 1 1 d . . . . .
O1 O 0.7250(3) 0.79486(8) 0.40417(6) 0.0419(3) Uani 1 1 d . . . . .
C5 C 0.3697(5) 0.58915(12) 0.36234(8) 0.0363(4) Uani 1 1 d . . . . .
C6 C 0.2857(4) 0.51089(11) 0.32292(8) 0.0304(4) Uani 1 1 d . . . . .
C7 C 0.1366(4) 0.43162(11) 0.34672(8) 0.0318(4) Uani 1 1 d . . . . .
C8 C 0.0691(5) 0.35698(12) 0.30928(8) 0.0355(4) Uani 1 1 d . . . . .
H8 H -0.030374 0.304141 0.324758 0.043 Uiso 1 1 calc R U . . .
C9 C 0.1480(5) 0.36053(12) 0.24948(8) 0.0366(4) Uani 1 1 d . . . . .
H9 H 0.102249 0.310002 0.224935 0.044 Uiso 1 1 calc R U . . .
C10 C 0.2960(5) 0.43916(11) 0.22542(8) 0.0330(4) Uani 1 1 d . . . . .
C11 C 0.3622(4) 0.51381(12) 0.26192(8) 0.0334(4) Uani 1 1 d . . . . .
H11 H 0.458519 0.566656 0.245912 0.040 Uiso 1 1 calc R U . . .
O2 O 0.3069(4) 0.58891(9) 0.41670(6) 0.0480(4) Uani 1 1 d . . . . .
O3 O 0.5171(4) 0.65930(9) 0.33669(6) 0.0516(4) Uani 1 1 d D . . . .
H3O H 0.574(6) 0.7047(15) 0.3643(9) 0.085(8) Uiso 1 1 d D . . . .
O4 O 0.0527(4) 0.42416(9) 0.40591(6) 0.0447(4) Uani 1 1 d . . . . .
H4O H 0.121(6) 0.4830(18) 0.4237(11) 0.079(8) Uiso 1 1 d . . . . .
O5 O 0.3836(4) 0.44538(9) 0.16634(6) 0.0479(4) Uani 1 1 d . . . . .
H5O H 0.333(6) 0.3910(17) 0.1426(11) 0.077(8) 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
C1 O1 1.264(2) . ?
C1 N2 1.346(2) . ?
C1 N1 1.372(2) . ?
C2 C3 1.329(2) . ?
C2 N1 1.360(2) . ?
C2 H2 0.9300 . ?
C3 F1 1.357(2) . ?
C3 C4 1.427(2) . ?
C4 N3 1.315(2) . ?
C4 N2 1.346(2) . ?
N1 H1N 0.96(2) . ?
N3 H2N 0.92(2) . ?
N3 H3N 0.86(2) . ?
C5 O2 1.242(2) . ?
C5 O3 1.307(2) . ?
C5 C6 1.467(2) . ?
C6 C11 1.400(2) . ?
C6 C7 1.400(2) . ?
C7 O4 1.371(2) . ?
C7 C8 1.389(2) . ?
C8 C9 1.376(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.393(2) . ?
C9 H9 0.9300 . ?
C10 O5 1.372(2) . ?
C10 C11 1.376(2) . ?
C11 H11 0.9300 . ?
O3 H3O 0.922(16) . ?
O4 H4O 0.98(3) . ?
O5 H5O 0.97(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
O1 C1 N2 121.40(14) . . ?
O1 C1 N1 118.59(15) . . ?
N2 C1 N1 120.01(16) . . ?
C3 C2 N1 118.44(15) . . ?
C3 C2 H2 120.8 . . ?
N1 C2 H2 120.8 . . ?
C2 C3 F1 121.58(14) . . ?
C2 C3 C4 120.42(16) . . ?
F1 C3 C4 117.99(15) . . ?
N3 C4 N2 119.70(15) . . ?
N3 C4 C3 120.75(16) . . ?
N2 C4 C3 119.54(15) . . ?
C2 N1 C1 121.86(15) . . ?
C2 N1 H1N 122.9(12) . . ?
C1 N1 H1N 115.2(12) . . ?
C1 N2 C4 119.67(13) . . ?
C4 N3 H2N 118.0(13) . . ?
C4 N3 H3N 118.2(13) . . ?
H2N N3 H3N 123.2(19) . . ?
O2 C5 O3 121.93(17) . . ?
O2 C5 C6 122.36(15) . . ?
O3 C5 C6 115.71(16) . . ?
C11 C6 C7 119.59(15) . . ?
C11 C6 C5 120.55(15) . . ?
C7 C6 C5 119.84(16) . . ?
O4 C7 C8 118.04(15) . . ?
O4 C7 C6 122.73(15) . . ?
C8 C7 C6 119.23(16) . . ?
C9 C8 C7 120.58(16) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 120.55(16) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
O5 C10 C11 117.93(15) . . ?
O5 C10 C9 122.59(16) . . ?
C11 C10 C9 119.48(16) . . ?
C10 C11 C6 120.56(15) . . ?
C10 C11 H11 119.7 . . ?
C6 C11 H11 119.7 . . ?
C5 O3 H3O 111.3(15) . . ?
C7 O4 H4O 104.6(14) . . ?
C10 O5 H5O 114.8(14) . . ?

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
N1 C2 C3 F1 179.69(15) . . . . ?
N1 C2 C3 C4 -1.8(3) . . . . ?
C2 C3 C4 N3 -177.87(17) . . . . ?
F1 C3 C4 N3 0.7(2) . . . . ?
C2 C3 C4 N2 1.2(3) . . . . ?
F1 C3 C4 N2 179.80(15) . . . . ?
C3 C2 N1 C1 0.0(3) . . . . ?
O1 C1 N1 C2 -178.35(16) . . . . ?
N2 C1 N1 C2 2.3(3) . . . . ?
O1 C1 N2 C4 177.83(16) . . . . ?
N1 C1 N2 C4 -2.9(2) . . . . ?
N3 C4 N2 C1 -179.76(16) . . . . ?
C3 C4 N2 C1 1.2(2) . . . . ?
O2 C5 C6 C11 -179.75(17) . . . . ?
O3 C5 C6 C11 -0.1(2) . . . . ?
O2 C5 C6 C7 -1.4(3) . . . . ?
O3 C5 C6 C7 178.22(16) . . . . ?
C11 C6 C7 O4 -179.57(16) . . . . ?
C5 C6 C7 O4 2.1(3) . . . . ?
C11 C6 C7 C8 0.4(3) . . . . ?
C5 C6 C7 C8 -177.96(16) . . . . ?
O4 C7 C8 C9 -179.94(16) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
C8 C9 C10 O5 179.08(16) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
O5 C10 C11 C6 -178.62(15) . . . . ?
C9 C10 C11 C6 0.7(3) . . . . ?
C7 C6 C11 C10 -0.8(3) . . . . ?
C5 C6 C11 C10 177.55(16) . . . . ?

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 H2N N2 0.92(2) 2.10(2) 3.009(2) 174.2(19) 3_776 yes
N3 H3N O5 0.86(2) 2.21(2) 2.948(2) 143.5(18) 4_576 yes
O5 H5O O1 0.97(3) 1.76(3) 2.723(2) 175(2) 2_645 yes
N1 H1N O2 0.96(2) 1.85(2) 2.810(2) 172.6(19) . yes
O3 H3O O1 0.922(16) 1.672(17) 2.583(2) 169(2) . yes
O4 H4O O2 0.98(3) 1.71(3) 2.596(2) 150(2) . yes

_refine_diff_density_max         0.236
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.052



_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_5FC-GEA_FIII
_database_code_depnum_ccdc_archive 'CCDC 2246416'
loop_
_audit_author_name
_audit_author_address
'Sunil Kumar Nechipadappu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'FLUCYTOSINE-GENTISATE form III'
_chemical_name_common            'FLUCYTOSINE-GENTISATE form III'
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H5 O4 1+, C4 H5 F N3 O 1-'
_chemical_formula_sum            'C11 H10 F N3 O5'
_chemical_formula_weight         283.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      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                   10.3556(4)
_cell_length_b                   8.6408(3)
_cell_length_c                   14.1363(6)
_cell_angle_alpha                90
_cell_angle_beta                 110.761(2)
_cell_angle_gamma                90
_cell_volume                     1182.79(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    6676
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      30.44

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.137
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6671
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            14116
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.816
_diffrn_reflns_theta_max         30.483
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3584
_reflns_number_gt                2682
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0662P)²+0.2123P] 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         3584
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1316
_refine_ls_wR_factor_gt          0.1177
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
C1 C 0.18829(12) 0.26843(14) 0.71381(8) 0.0341(2) Uani 1 1 d . . . . .
C2 C -0.01008(13) 0.10282(15) 0.66294(9) 0.0385(3) Uani 1 1 d . . . . .
H2 H -0.063472 0.029479 0.680391 0.046 Uiso 1 1 calc R U . . .
C3 C -0.04401(12) 0.14808(14) 0.56689(9) 0.0347(3) Uani 1 1 d . . . . .
C4 C 0.03670(10) 0.25945(13) 0.53859(8) 0.0286(2) Uani 1 1 d . . . . .
F1 F -0.15448(8) 0.09326(11) 0.49182(6) 0.0539(3) Uani 1 1 d . . . . .
N1 N 0.10324(11) 0.16465(13) 0.73531(8) 0.0386(2) Uani 1 1 d . . . . .
H1N H 0.1321(19) 0.133(2) 0.8018(14) 0.064(5) Uiso 1 1 d . . . . .
N2 N 0.14862(9) 0.31468(12) 0.61392(7) 0.0314(2) Uani 1 1 d . . . . .
H2N H 0.2086(17) 0.390(2) 0.6001(12) 0.053(4) Uiso 1 1 d . . . . .
N3 N 0.00688(10) 0.30727(13) 0.44597(7) 0.0359(2) Uani 1 1 d . . . . .
H3N H 0.0640(16) 0.3785(19) 0.4327(11) 0.043(4) Uiso 1 1 d . . . . .
H4N H -0.0657(19) 0.270(2) 0.3964(13) 0.058(5) Uiso 1 1 d . . . . .
O1 O 0.29330(10) 0.32000(13) 0.77735(7) 0.0509(3) Uani 1 1 d . . . . .
C5 C 0.28595(11) 0.57043(13) 0.48365(8) 0.0309(2) Uani 1 1 d . . . . .
C6 C 0.38540(11) 0.67332(13) 0.45915(8) 0.0295(2) Uani 1 1 d . . . . .
C7 C 0.35879(13) 0.72276(16) 0.35970(8) 0.0373(3) Uani 1 1 d . . . . .
C8 C 0.45243(14) 0.81917(17) 0.33811(9) 0.0436(3) Uani 1 1 d . . . . .
H8 H 0.434501 0.851925 0.272006 0.052 Uiso 1 1 calc R U . . .
C9 C 0.57148(13) 0.86645(16) 0.41390(10) 0.0401(3) Uani 1 1 d . . . . .
H9 H 0.633115 0.931435 0.398804 0.048 Uiso 1 1 calc R U . . .
C10 C 0.59981(12) 0.81724(14) 0.51303(9) 0.0344(3) Uani 1 1 d . . . . .
C11 C 0.50684(11) 0.72161(13) 0.53487(8) 0.0312(2) Uani 1 1 d . . . . .
H11 H 0.525616 0.689007 0.601110 0.037 Uiso 1 1 calc R U . . .
O2 O 0.30730(9) 0.53463(10) 0.57445(6) 0.0361(2) Uani 1 1 d . . . . .
O3 O 0.18103(9) 0.52258(12) 0.41056(6) 0.0428(2) Uani 1 1 d . . . . .
O4 O 0.24131(12) 0.67942(15) 0.28210(7) 0.0589(3) Uani 1 1 d . . . . .
H4O H 0.195(3) 0.611(3) 0.3152(19) 0.105(8) Uiso 1 1 d . . . . .
O5 O 0.72089(10) 0.86408(13) 0.58500(8) 0.0511(3) Uani 1 1 d . . . . .
H5O H 0.721(2) 0.842(2) 0.6447(17) 0.078(6) 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
C1 O1 1.2229(14) . ?
C1 N1 1.3645(16) . ?
C1 N2 1.3825(14) . ?
C2 C3 1.3349(16) . ?
C2 N1 1.3631(16) . ?
C2 H2 0.9300 . ?
C3 F1 1.3411(13) . ?
C3 C4 1.4219(16) . ?
C4 N3 1.3014(14) . ?
C4 N2 1.3528(13) . ?
N1 H1N 0.921(19) . ?
N2 H2N 0.966(18) . ?
N3 H3N 0.918(17) . ?
N3 H4N 0.887(18) . ?
C5 O2 1.2614(13) . ?
C5 O3 1.2740(13) . ?
C5 C6 1.4913(15) . ?
C6 C11 1.3954(15) . ?
C6 C7 1.4000(15) . ?
C7 O4 1.3703(14) . ?
C7 C8 1.3918(18) . ?
C8 C9 1.3777(18) . ?
C8 H8 0.9300 . ?
C9 C10 1.3925(17) . ?
C9 H9 0.9300 . ?
C10 O5 1.3663(14) . ?
C10 C11 1.3841(15) . ?
C11 H11 0.9300 . ?
O4 H4O 0.98(3) . ?
O5 H5O 0.86(2) . ?

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
O1 C1 N1 123.51(10) . . ?
O1 C1 N2 120.64(11) . . ?
N1 C1 N2 115.84(10) . . ?
C3 C2 N1 119.66(11) . . ?
C3 C2 H2 120.2 . . ?
N1 C2 H2 120.2 . . ?
C2 C3 F1 122.99(11) . . ?
C2 C3 C4 121.03(10) . . ?
F1 C3 C4 115.98(10) . . ?
N3 C4 N2 120.77(10) . . ?
N3 C4 C3 122.99(10) . . ?
N2 C4 C3 116.25(9) . . ?
C2 N1 C1 122.84(10) . . ?
C2 N1 H1N 122.1(12) . . ?
C1 N1 H1N 114.8(12) . . ?
C4 N2 C1 124.30(10) . . ?
C4 N2 H2N 120.8(10) . . ?
C1 N2 H2N 114.9(10) . . ?
C4 N3 H3N 118.6(10) . . ?
C4 N3 H4N 120.8(11) . . ?
H3N N3 H4N 120.6(15) . . ?
O2 C5 O3 122.49(10) . . ?
O2 C5 C6 119.75(10) . . ?
O3 C5 C6 117.76(9) . . ?
C11 C6 C7 118.82(10) . . ?
C11 C6 C5 120.59(9) . . ?
C7 C6 C5 120.59(10) . . ?
O4 C7 C8 118.55(11) . . ?
O4 C7 C6 121.55(11) . . ?
C8 C7 C6 119.90(11) . . ?
C9 C8 C7 120.52(11) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 120.22(11) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
O5 C10 C11 122.55(11) . . ?
O5 C10 C9 117.99(11) . . ?
C11 C10 C9 119.45(11) . . ?
C10 C11 C6 121.09(10) . . ?
C10 C11 H11 119.5 . . ?
C6 C11 H11 119.5 . . ?
C7 O4 H4O 103.2(14) . . ?
C10 O5 H5O 110.2(14) . . ?

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
N1 C2 C3 F1 -179.49(11) . . . . ?
N1 C2 C3 C4 0.3(2) . . . . ?
C2 C3 C4 N3 -179.65(12) . . . . ?
F1 C3 C4 N3 0.19(18) . . . . ?
C2 C3 C4 N2 0.43(18) . . . . ?
F1 C3 C4 N2 -179.72(10) . . . . ?
C3 C2 N1 C1 -2.4(2) . . . . ?
O1 C1 N1 C2 -176.93(13) . . . . ?
N2 C1 N1 C2 3.44(18) . . . . ?
N3 C4 N2 C1 -179.13(11) . . . . ?
C3 C4 N2 C1 0.78(17) . . . . ?
O1 C1 N2 C4 177.71(11) . . . . ?
N1 C1 N2 C4 -2.64(18) . . . . ?
O2 C5 C6 C11 4.52(17) . . . . ?
O3 C5 C6 C11 -175.86(11) . . . . ?
O2 C5 C6 C7 -175.69(11) . . . . ?
O3 C5 C6 C7 3.93(17) . . . . ?
C11 C6 C7 O4 -179.92(12) . . . . ?
C5 C6 C7 O4 0.28(19) . . . . ?
C11 C6 C7 C8 -0.40(19) . . . . ?
C5 C6 C7 C8 179.80(12) . . . . ?
O4 C7 C8 C9 179.58(13) . . . . ?
C6 C7 C8 C9 0.1(2) . . . . ?
C7 C8 C9 C10 0.4(2) . . . . ?
C8 C9 C10 O5 178.34(12) . . . . ?
C8 C9 C10 C11 -0.6(2) . . . . ?
O5 C10 C11 C6 -178.65(11) . . . . ?
C9 C10 C11 C6 0.20(18) . . . . ?
C7 C6 C11 C10 0.28(18) . . . . ?
C5 C6 C11 C10 -179.92(10) . . . . ?

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
N1 H1N O2 0.921(19) 1.843(19) 2.7543(13) 169.5(17) 2_546 yes
N3 H4N O1 0.887(18) 1.956(19) 2.8364(13) 171.6(16) 4_565 yes
O5 H5O O4 0.86(2) 1.89(2) 2.7443(15) 171(2) 4_676 yes
N2 H2N O2 0.966(18) 1.732(18) 2.6969(13) 176.1(16) . yes
N3 H3N O3 0.918(17) 1.840(17) 2.7576(14) 178.1(14) . yes
O4 H4O O3 0.98(3) 1.60(3) 2.5154(14) 154(2) . yes

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.043



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ETHANOL-WATER'
