# 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. 
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data_5fc_caf_3
_database_code_depnum_ccdc_archive 'CCDC 1817618'
_audit_update_record             
;
2018-07-17 deposited with the CCDC.
2018-07-26 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_5fc_caf_3           
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.949 Why?
RESPONSE: Some reflections, with high difference | Error / esd |, were omitted for better convergence of refinement, including some close to beamstop.
;
_vrf_PLAT910_5fc_caf_3           
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         12 Note
RESPONSE: Some reflections, with high difference | Error / esd |, were omitted for better convergence of refinement, including some close to beamstop.
;
# Added during the CSD deposition process: Tuesday 17 July 2018 09:27 PM
# end Validation Reply Form

_audit_creation_date             2018-07-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            
'5-Fluorocytosine; 5-Flucytosine; 5-FC; 5FC-CAF'
_chemical_name_systematic        '5-Fluorocytosine caffeine cocrystal'
_chemical_formula_moiety         '2(C4 H4 F N3 O), 2(C8 H10 N4 O2)'
_chemical_formula_sum            'C24 H28 F2 N14 O6'
_chemical_formula_weight         646.60
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   9.1890(6)
_cell_length_b                   22.4128(17)
_cell_length_c                   13.3425(13)
_cell_angle_alpha                90
_cell_angle_beta                 93.485(8)
_cell_angle_gamma                90
_cell_volume                     2742.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5556
_cell_measurement_temperature    298
_cell_measurement_theta_max      28.7880
_cell_measurement_theta_min      3.6380
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0682
_diffrn_reflns_av_unetI/netI     0.0701
_diffrn_reflns_Laue_measured_fraction_full 0.949
_diffrn_reflns_Laue_measured_fraction_max 0.802
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17471
_diffrn_reflns_point_group_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.802
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.592
_diffrn_reflns_theta_min         3.315
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.949
_diffrn_measured_fraction_theta_max 0.802
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3818
_reflns_number_total             6188
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         6188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0671
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1215P)²+0.3943P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1896
_refine_ls_wR_factor_ref         0.2286
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1'(H1'), N1(H1), C6'(H6'), C6(H6), C7'(H7'), C7(H7)
2.b X=CH2 refined with riding coordinates:
 N41(H41A,H41B), N41'(H41C,H41D)
2.c Idealised Me refined as rotating group:
 C13(H13D,H13E,H13F), C12'(H12A,H12B,H12C), C14(H14D,H14E,H14F), C14'(H14A,
 H14B,H14C), C13'(H13A,H13B,H13C), C12(H12D,H12E,H12F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.01788(17) 0.13267(6) 0.33366(16) 0.0581(5) Uani 1 1 d . . . . .
F51' F 0.52637(17) 0.50249(6) 0.38080(16) 0.0605(5) Uani 1 1 d . . . . .
O21 O 0.04786(19) 0.37008(8) 0.33212(18) 0.0505(5) Uani 1 1 d . . . . .
O21' O 0.54591(19) 0.26760(8) 0.32274(18) 0.0518(6) Uani 1 1 d . . . . .
O3' O 1.3263(2) 0.63314(9) 0.40899(18) 0.0557(6) Uani 1 1 d . . . . .
O4' O 0.9710(2) 0.77517(8) 0.42715(18) 0.0552(6) Uani 1 1 d . . . . .
N1' N 0.4131(2) 0.35148(9) 0.34348(19) 0.0437(6) Uani 1 1 d . . . . .
H1' H 0.3338 0.3310 0.3396 0.052 Uiso 1 1 calc R . . . .
N3 N 0.1661(2) 0.28118(8) 0.33324(18) 0.0381(5) Uani 1 1 d . . . . .
O3 O 0.8164(2) 0.00402(9) 0.36696(18) 0.0574(6) Uani 1 1 d . . . . .
N8' N 0.7541(2) 0.67221(9) 0.41353(18) 0.0402(5) Uani 1 1 d . . . . .
N41 N 0.2839(2) 0.19097(9) 0.33696(19) 0.0458(6) Uani 1 1 d . . . . .
H41A H 0.3661 0.2093 0.3381 0.055 Uiso 1 1 calc R . . . .
H41B H 0.2817 0.1526 0.3376 0.055 Uiso 1 1 calc R . . . .
O4 O 0.4688(2) -0.13613(8) 0.4216(2) 0.0633(7) Uani 1 1 d . . . . .
N3' N 0.6666(2) 0.35561(8) 0.33753(18) 0.0392(5) Uani 1 1 d . . . . .
N10' N 1.1481(2) 0.70287(9) 0.42093(18) 0.0408(5) Uani 1 1 d . . . . .
N9 N 0.5805(2) 0.03557(9) 0.35764(18) 0.0408(5) Uani 1 1 d . . . . .
N10 N 0.6413(2) -0.06521(9) 0.39210(19) 0.0416(5) Uani 1 1 d . . . . .
N8 N 0.2469(2) -0.03663(9) 0.3869(2) 0.0455(6) Uani 1 1 d . . . . .
N41' N 0.7879(2) 0.44470(9) 0.3582(2) 0.0469(6) Uani 1 1 d . . . . .
H41C H 0.8688 0.4264 0.3505 0.056 Uiso 1 1 calc R . . . .
H41D H 0.7878 0.4826 0.3686 0.056 Uiso 1 1 calc R . . . .
N1 N -0.0882(2) 0.28594(9) 0.32700(19) 0.0428(6) Uani 1 1 d . . . . .
H1 H -0.1668 0.3068 0.3241 0.051 Uiso 1 1 calc R . . . .
N9' N 1.0916(2) 0.60027(9) 0.40338(18) 0.0418(5) Uani 1 1 d . . . . .
N7 N 0.3201(2) 0.05729(10) 0.3521(2) 0.0486(6) Uani 1 1 d . . . . .
N7' N 0.8318(2) 0.57733(9) 0.4005(2) 0.0483(6) Uani 1 1 d . . . . .
C4 C 0.1604(3) 0.22181(10) 0.3342(2) 0.0355(6) Uani 1 1 d . . . . .
C8' C 0.9035(3) 0.67343(10) 0.4145(2) 0.0376(6) Uani 1 1 d . . . . .
C9' C 0.9464(3) 0.61532(11) 0.4058(2) 0.0384(6) Uani 1 1 d . . . . .
C10' C 1.0021(3) 0.72220(11) 0.4210(2) 0.0397(6) Uani 1 1 d . . . . .
C2 C 0.0433(2) 0.31485(10) 0.3303(2) 0.0374(6) Uani 1 1 d . . . . .
C4' C 0.6636(3) 0.41455(10) 0.3539(2) 0.0356(6) Uani 1 1 d . . . . .
C6' C 0.4048(3) 0.41075(11) 0.3591(2) 0.0431(6) Uani 1 1 d . . . . .
H6' H 0.3151 0.4291 0.3654 0.052 Uiso 1 1 calc R . . . .
C5 C 0.0223(3) 0.19295(10) 0.3320(2) 0.0394(6) Uani 1 1 d . . . . .
C2' C 0.5435(2) 0.32231(10) 0.3335(2) 0.0380(6) Uani 1 1 d . . . . .
C9 C 0.4366(3) 0.02035(11) 0.3637(2) 0.0392(6) Uani 1 1 d . . . . .
C10 C 0.4977(3) -0.08423(11) 0.4013(2) 0.0407(6) Uani 1 1 d . . . . .
C8 C 0.3965(3) -0.03680(10) 0.3849(2) 0.0386(6) Uani 1 1 d . . . . .
C6 C -0.0991(3) 0.22545(11) 0.3281(2) 0.0418(6) Uani 1 1 d . . . . .
H6 H -0.1900 0.2071 0.3261 0.050 Uiso 1 1 calc R . . . .
C5' C 0.5282(3) 0.44281(10) 0.3653(2) 0.0408(6) Uani 1 1 d . . . . .
C11' C 1.1966(3) 0.64446(11) 0.4104(2) 0.0401(6) Uani 1 1 d . . . . .
C11 C 0.6878(3) -0.00766(11) 0.3713(2) 0.0412(6) Uani 1 1 d . . . . .
C7' C 0.7168(3) 0.61434(11) 0.4050(2) 0.0480(7) Uani 1 1 d . . . . .
H7' H 0.6207 0.6011 0.4025 0.058 Uiso 1 1 calc R . . . .
C7 C 0.2073(3) 0.02078(12) 0.3670(3) 0.0529(8) Uani 1 1 d . . . . .
H7 H 0.1109 0.0336 0.3640 0.064 Uiso 1 1 calc R . . . .
C13 C 0.7555(3) -0.11063(12) 0.4043(3) 0.0558(8) Uani 1 1 d . . . . .
H13D H 0.7122 -0.1485 0.4177 0.084 Uiso 1 1 calc GR . . . .
H13E H 0.8226 -0.0999 0.4593 0.084 Uiso 1 1 calc GR . . . .
H13F H 0.8067 -0.1132 0.3438 0.084 Uiso 1 1 calc GR . . . .
C12' C 0.6517(3) 0.72187(13) 0.4176(3) 0.0572(8) Uani 1 1 d . . . . .
H12A H 0.6748 0.7451 0.4769 0.086 Uiso 1 1 calc GR . . . .
H12B H 0.5543 0.7066 0.4193 0.086 Uiso 1 1 calc GR . . . .
H12C H 0.6587 0.7465 0.3593 0.086 Uiso 1 1 calc GR . . . .
C14 C 0.6201(3) 0.09703(12) 0.3349(3) 0.0598(9) Uani 1 1 d . . . . .
H14D H 0.5707 0.1091 0.2727 0.090 Uiso 1 1 calc GR . . . .
H14E H 0.7236 0.0996 0.3292 0.090 Uiso 1 1 calc GR . . . .
H14F H 0.5921 0.1228 0.3879 0.090 Uiso 1 1 calc GR . . . .
C14' C 1.1344(4) 0.53873(11) 0.3860(3) 0.0578(8) Uani 1 1 d . . . . .
H14A H 1.0901 0.5131 0.4331 0.087 Uiso 1 1 calc GR . . . .
H14B H 1.2386 0.5353 0.3946 0.087 Uiso 1 1 calc GR . . . .
H14C H 1.1027 0.5272 0.3189 0.087 Uiso 1 1 calc GR . . . .
C13' C 1.2621(3) 0.74911(12) 0.4283(3) 0.0562(8) Uani 1 1 d . . . . .
H13A H 1.2180 0.7874 0.4371 0.084 Uiso 1 1 calc GR . . . .
H13B H 1.3138 0.7493 0.3679 0.084 Uiso 1 1 calc GR . . . .
H13C H 1.3289 0.7407 0.4847 0.084 Uiso 1 1 calc GR . . . .
C12 C 0.1476(3) -0.08560(14) 0.4029(3) 0.0667(10) Uani 1 1 d . . . . .
H12D H 0.1609 -0.1162 0.3540 0.100 Uiso 1 1 calc GR . . . .
H12E H 0.0490 -0.0714 0.3962 0.100 Uiso 1 1 calc GR . . . .
H12F H 0.1672 -0.1016 0.4690 0.100 Uiso 1 1 calc GR . . . .


_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 1.352(3) . ?
F51' C5' 1.354(3) . ?
O21 C2 1.239(3) . ?
O21' C2' 1.235(3) . ?
O3' C11' 1.220(3) . ?
O4' C10' 1.225(3) . ?
N1' H1' 0.8600 . ?
N1' C6' 1.347(3) . ?
N1' C2' 1.379(3) . ?
N3 C4 1.332(3) . ?
N3 C2 1.356(3) . ?
O3 C11 1.215(3) . ?
N8' C8' 1.373(3) . ?
N8' C7' 1.345(3) . ?
N8' C12' 1.460(3) . ?
N41 H41A 0.8600 . ?
N41 H41B 0.8600 . ?
N41 C4 1.327(3) . ?
O4 C10 1.227(3) . ?
N3' C4' 1.339(3) . ?
N3' C2' 1.354(3) . ?
N10' C10' 1.409(3) . ?
N10' C11' 1.393(3) . ?
N10' C13' 1.473(3) . ?
N9 C9 1.372(3) . ?
N9 C11 1.387(3) . ?
N9 C14 1.461(3) . ?
N10 C10 1.399(3) . ?
N10 C11 1.392(3) . ?
N10 C13 1.464(3) . ?
N8 C8 1.377(3) . ?
N8 C7 1.359(3) . ?
N8 C12 1.452(3) . ?
N41' H41C 0.8600 . ?
N41' H41D 0.8600 . ?
N41' C4' 1.325(3) . ?
N1 H1 0.8600 . ?
N1 C2 1.369(3) . ?
N1 C6 1.360(3) . ?
N9' C9' 1.379(3) . ?
N9' C11' 1.382(3) . ?
N9' C14' 1.457(3) . ?
N7 C9 1.355(3) . ?
N7 C7 1.345(4) . ?
N7' C9' 1.353(3) . ?
N7' C7' 1.348(3) . ?
C4 C5 1.423(3) . ?
C8' C9' 1.368(3) . ?
C8' C10' 1.419(3) . ?
C4' C5' 1.413(3) . ?
C6' H6' 0.9300 . ?
C6' C5' 1.340(3) . ?
C5 C6 1.331(3) . ?
C9 C8 1.367(3) . ?
C10 C8 1.420(3) . ?
C6 H6 0.9300 . ?
C7' H7' 0.9300 . ?
C7 H7 0.9300 . ?
C13 H13D 0.9600 . ?
C13 H13E 0.9600 . ?
C13 H13F 0.9600 . ?
C12' H12A 0.9600 . ?
C12' H12B 0.9600 . ?
C12' H12C 0.9600 . ?
C14 H14D 0.9600 . ?
C14 H14E 0.9600 . ?
C14 H14F 0.9600 . ?
C14' H14A 0.9600 . ?
C14' H14B 0.9600 . ?
C14' H14C 0.9600 . ?
C13' H13A 0.9600 . ?
C13' H13B 0.9600 . ?
C13' H13C 0.9600 . ?
C12 H12D 0.9600 . ?
C12 H12E 0.9600 . ?
C12 H12F 0.9600 . ?

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
C6' N1' H1' 118.7 . . ?
C6' N1' C2' 122.7(2) . . ?
C2' N1' H1' 118.7 . . ?
C4 N3 C2 121.55(19) . . ?
C8' N8' C12' 129.1(2) . . ?
C7' N8' C8' 105.7(2) . . ?
C7' N8' C12' 125.2(2) . . ?
H41A N41 H41B 120.0 . . ?
C4 N41 H41A 120.0 . . ?
C4 N41 H41B 120.0 . . ?
C4' N3' C2' 121.66(19) . . ?
C10' N10' C13' 117.2(2) . . ?
C11' N10' C10' 126.9(2) . . ?
C11' N10' C13' 115.9(2) . . ?
C9 N9 C11 119.9(2) . . ?
C9 N9 C14 120.0(2) . . ?
C11 N9 C14 120.1(2) . . ?
C10 N10 C13 116.9(2) . . ?
C11 N10 C10 127.1(2) . . ?
C11 N10 C13 116.0(2) . . ?
C8 N8 C12 129.7(2) . . ?
C7 N8 C8 104.8(2) . . ?
C7 N8 C12 125.5(2) . . ?
H41C N41' H41D 120.0 . . ?
C4' N41' H41C 120.0 . . ?
C4' N41' H41D 120.0 . . ?
C2 N1 H1 118.8 . . ?
C6 N1 H1 118.8 . . ?
C6 N1 C2 122.5(2) . . ?
C9' N9' C11' 119.7(2) . . ?
C9' N9' C14' 120.4(2) . . ?
C11' N9' C14' 119.7(2) . . ?
C7 N7 C9 102.8(2) . . ?
C7' N7' C9' 102.7(2) . . ?
N3 C4 C5 119.3(2) . . ?
N41 C4 N3 119.1(2) . . ?
N41 C4 C5 121.6(2) . . ?
N8' C8' C10' 130.6(2) . . ?
C9' C8' N8' 105.9(2) . . ?
C9' C8' C10' 123.5(2) . . ?
N7' C9' N9' 126.6(2) . . ?
N7' C9' C8' 112.1(2) . . ?
C8' C9' N9' 121.3(2) . . ?
O4' C10' N10' 121.6(2) . . ?
O4' C10' C8' 126.9(2) . . ?
N10' C10' C8' 111.5(2) . . ?
O21 C2 N3 121.9(2) . . ?
O21 C2 N1 120.1(2) . . ?
N3 C2 N1 117.9(2) . . ?
N3' C4' C5' 119.1(2) . . ?
N41' C4' N3' 118.9(2) . . ?
N41' C4' C5' 121.9(2) . . ?
N1' C6' H6' 120.6 . . ?
C5' C6' N1' 118.9(2) . . ?
C5' C6' H6' 120.6 . . ?
F51 C5 C4 118.8(2) . . ?
C6 C5 F51 121.4(2) . . ?
C6 C5 C4 119.8(2) . . ?
O21' C2' N1' 120.3(2) . . ?
O21' C2' N3' 122.1(2) . . ?
N3' C2' N1' 117.6(2) . . ?
N7 C9 N9 126.8(2) . . ?
N7 C9 C8 112.0(2) . . ?
C8 C9 N9 121.2(2) . . ?
O4 C10 N10 121.7(2) . . ?
O4 C10 C8 126.5(2) . . ?
N10 C10 C8 111.7(2) . . ?
N8 C8 C10 130.1(2) . . ?
C9 C8 N8 106.4(2) . . ?
C9 C8 C10 123.4(2) . . ?
N1 C6 H6 120.5 . . ?
C5 C6 N1 118.9(2) . . ?
C5 C6 H6 120.5 . . ?
F51' C5' C4' 118.6(2) . . ?
C6' C5' F51' 121.4(2) . . ?
C6' C5' C4' 120.0(2) . . ?
O3' C11' N10' 121.1(2) . . ?
O3' C11' N9' 121.9(2) . . ?
N9' C11' N10' 117.0(2) . . ?
O3 C11 N9 122.0(2) . . ?
O3 C11 N10 121.4(2) . . ?
N9 C11 N10 116.7(2) . . ?
N8' C7' N7' 113.6(2) . . ?
N8' C7' H7' 123.2 . . ?
N7' C7' H7' 123.2 . . ?
N8 C7 H7 123.1 . . ?
N7 C7 N8 113.9(2) . . ?
N7 C7 H7 123.1 . . ?
N10 C13 H13D 109.5 . . ?
N10 C13 H13E 109.5 . . ?
N10 C13 H13F 109.5 . . ?
H13D C13 H13E 109.5 . . ?
H13D C13 H13F 109.5 . . ?
H13E C13 H13F 109.5 . . ?
N8' C12' H12A 109.5 . . ?
N8' C12' H12B 109.5 . . ?
N8' C12' H12C 109.5 . . ?
H12A C12' H12B 109.5 . . ?
H12A C12' H12C 109.5 . . ?
H12B C12' H12C 109.5 . . ?
N9 C14 H14D 109.5 . . ?
N9 C14 H14E 109.5 . . ?
N9 C14 H14F 109.5 . . ?
H14D C14 H14E 109.5 . . ?
H14D C14 H14F 109.5 . . ?
H14E C14 H14F 109.5 . . ?
N9' C14' H14A 109.5 . . ?
N9' C14' H14B 109.5 . . ?
N9' C14' H14C 109.5 . . ?
H14A C14' H14B 109.5 . . ?
H14A C14' H14C 109.5 . . ?
H14B C14' H14C 109.5 . . ?
N10' C13' H13A 109.5 . . ?
N10' C13' H13B 109.5 . . ?
N10' C13' H13C 109.5 . . ?
H13A C13' H13B 109.5 . . ?
H13A C13' H13C 109.5 . . ?
H13B C13' H13C 109.5 . . ?
N8 C12 H12D 109.5 . . ?
N8 C12 H12E 109.5 . . ?
N8 C12 H12F 109.5 . . ?
H12D C12 H12E 109.5 . . ?
H12D C12 H12F 109.5 . . ?
H12E C12 H12F 109.5 . . ?

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
F51 C5 C6 N1 179.7(2) . . . . ?
N1' C6' C5' F51' 179.9(3) . . . . ?
N1' C6' C5' C4' 1.0(4) . . . . ?
N3 C4 C5 F51 -179.6(2) . . . . ?
N3 C4 C5 C6 0.6(4) . . . . ?
N8' C8' C9' N9' 179.4(2) . . . . ?
N8' C8' C9' N7' -0.7(3) . . . . ?
N8' C8' C10' O4' -0.2(5) . . . . ?
N8' C8' C10' N10' 179.1(3) . . . . ?
N41 C4 C5 F51 0.6(4) . . . . ?
N41 C4 C5 C6 -179.2(3) . . . . ?
O4 C10 C8 N8 -0.4(5) . . . . ?
O4 C10 C8 C9 179.2(3) . . . . ?
N3' C4' C5' F51' -179.3(2) . . . . ?
N3' C4' C5' C6' -0.4(4) . . . . ?
N9 C9 C8 N8 179.1(2) . . . . ?
N9 C9 C8 C10 -0.5(4) . . . . ?
N10 C10 C8 N8 179.9(3) . . . . ?
N10 C10 C8 C9 -0.5(4) . . . . ?
N41' C4' C5' F51' 0.2(4) . . . . ?
N41' C4' C5' C6' 179.1(3) . . . . ?
N7 C9 C8 N8 0.2(3) . . . . ?
N7 C9 C8 C10 -179.5(3) . . . . ?
C4 N3 C2 O21 178.1(3) . . . . ?
C4 N3 C2 N1 -0.9(4) . . . . ?
C4 C5 C6 N1 -0.5(4) . . . . ?
C8' N8' C7' N7' 0.1(3) . . . . ?
C9' N9' C11' O3' 179.7(3) . . . . ?
C9' N9' C11' N10' 0.7(4) . . . . ?
C9' N7' C7' N8' -0.5(3) . . . . ?
C9' C8' C10' O4' 178.6(3) . . . . ?
C9' C8' C10' N10' -2.1(4) . . . . ?
C10' N10' C11' O3' 178.2(3) . . . . ?
C10' N10' C11' N9' -2.8(4) . . . . ?
C10' C8' C9' N9' 0.4(4) . . . . ?
C10' C8' C9' N7' -179.7(3) . . . . ?
C2 N3 C4 N41 180.0(3) . . . . ?
C2 N3 C4 C5 0.1(4) . . . . ?
C2 N1 C6 C5 -0.4(4) . . . . ?
C4' N3' C2' O21' -176.8(3) . . . . ?
C4' N3' C2' N1' 2.1(4) . . . . ?
C6' N1' C2' O21' 177.5(3) . . . . ?
C6' N1' C2' N3' -1.5(4) . . . . ?
C2' N1' C6' C5' -0.1(4) . . . . ?
C2' N3' C4' N41' 179.3(3) . . . . ?
C2' N3' C4' C5' -1.2(4) . . . . ?
C9 N9 C11 O3 -179.7(3) . . . . ?
C9 N9 C11 N10 -0.8(4) . . . . ?
C9 N7 C7 N8 -0.2(4) . . . . ?
C10 N10 C11 O3 178.5(3) . . . . ?
C10 N10 C11 N9 -0.4(4) . . . . ?
C8 N8 C7 N7 0.3(4) . . . . ?
C6 N1 C2 O21 -177.9(3) . . . . ?
C6 N1 C2 N3 1.1(4) . . . . ?
C11' N10' C10' O4' -177.3(3) . . . . ?
C11' N10' C10' C8' 3.4(4) . . . . ?
C11' N9' C9' N7' -179.5(3) . . . . ?
C11' N9' C9' C8' 0.4(4) . . . . ?
C11 N9 C9 N7 -180.0(3) . . . . ?
C11 N9 C9 C8 1.2(4) . . . . ?
C11 N10 C10 O4 -178.7(3) . . . . ?
C11 N10 C10 C8 1.0(4) . . . . ?
C7' N8' C8' C9' 0.3(3) . . . . ?
C7' N8' C8' C10' 179.3(3) . . . . ?
C7' N7' C9' N9' -179.4(3) . . . . ?
C7' N7' C9' C8' 0.7(3) . . . . ?
C7 N8 C8 C9 -0.2(3) . . . . ?
C7 N8 C8 C10 179.4(3) . . . . ?
C7 N7 C9 N9 -178.9(3) . . . . ?
C7 N7 C9 C8 0.0(3) . . . . ?
C13 N10 C10 O4 2.1(4) . . . . ?
C13 N10 C10 C8 -178.1(3) . . . . ?
C13 N10 C11 O3 -2.3(4) . . . . ?
C13 N10 C11 N9 178.8(3) . . . . ?
C12' N8' C8' C9' -178.0(3) . . . . ?
C12' N8' C8' C10' 1.0(5) . . . . ?
C12' N8' C7' N7' 178.5(3) . . . . ?
C14 N9 C9 N7 -1.1(4) . . . . ?
C14 N9 C9 C8 -179.9(3) . . . . ?
C14 N9 C11 O3 1.5(4) . . . . ?
C14 N9 C11 N10 -179.6(3) . . . . ?
C14' N9' C9' N7' 5.1(4) . . . . ?
C14' N9' C9' C8' -175.1(3) . . . . ?
C14' N9' C11' O3' -4.8(4) . . . . ?
C14' N9' C11' N10' 176.2(2) . . . . ?
C13' N10' C10' O4' -0.1(4) . . . . ?
C13' N10' C10' C8' -179.5(3) . . . . ?
C13' N10' C11' O3' 1.0(4) . . . . ?
C13' N10' C11' N9' 180.0(3) . . . . ?
C12 N8 C8 C9 178.0(3) . . . . ?
C12 N8 C8 C10 -2.4(5) . . . . ?
C12 N8 C7 N7 -178.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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-paba
_database_code_depnum_ccdc_archive 'CCDC 1817630'
_audit_update_record             
;
2018-07-17 deposited with the CCDC.
2018-07-26 downloaded from the CCDC.
;
_audit_creation_date             2017-08-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            
'5-Fluorocytosine; 5-Flucytosine; 5-FC; 5FC-PABA'
_chemical_name_systematic        
'5-Fluorocytosine p-aminobenzoic acid cocrystal'
_chemical_formula_moiety         'C4 H4 F N3 O, C7 H7 N O2'
_chemical_formula_sum            'C11 H11 F N4 O3'
_chemical_formula_weight         266.24
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   4.8695(3)
_cell_length_b                   24.4911(16)
_cell_length_c                   9.8792(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.567(6)
_cell_angle_gamma                90
_cell_volume                     1167.92(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5687
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.3520
_cell_measurement_theta_min      4.1420
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68237
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0642
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            19318
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         3.925
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 5.2923
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00  84.00   1.00   20.00    --   11.26  57.00 -60.00  101
  2  ω    -84.00  17.00   1.00   20.00    --  -11.49 -57.00   0.00  101
  3  ω    -40.00  62.00   1.00   20.00    --  -11.49  57.00 150.00  102
  4  ω    -63.00  36.00   1.00   20.00    --   11.26 -38.00 -60.00   99
  5  ω    -20.00  52.00   1.00   20.00    --   11.26 -99.00 -90.00   72
  6  ω     34.00  98.00   1.00   20.00    --   11.26-178.00 150.00   64
  7  ω    -13.00  45.00   1.00   20.00    --   11.26  38.00-150.00   58
  8  ω    -20.00  29.00   1.00   20.00    --  -11.49 -99.00 150.00   49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2204
_reflns_number_total             2671
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2671
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0565
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0615P)²+0.6472P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1426
_refine_ls_wR_factor_ref         0.1500
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Rigid body (RIGU) restrains
 C9, C8, C13', C12', C11, C10
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Fixed Sof: C12'(0.45) H12'(0.45) C13'(0.45) H13'(0.45) C9(0.55) H9(0.55)
 C10(0.55) H10(0.55) C13(0.55) H13(0.55) C12(0.55) H12(0.55) C9'(0.45)
 H9'(0.45) C10'(0.45) H10'(0.45)
4.a Rotating group:
 N4(H4A,H4B)
4.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C12'(H12'), C13'(H13'), C9(H9), C10(H10), C13(H13), C12(H12),
 C9'(H9'), C10'(H10')
4.c X=CH2 refined with riding coordinates:
 N41(H41A,H41B)
4.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 1.2139(3) 0.38927(5) 0.73200(14) 0.0533(4) Uani 1 1 d . . . . .
O21 O 0.6099(3) 0.55150(6) 0.89420(15) 0.0464(4) Uani 1 1 d . . . . .
O3 O 0.4557(3) 0.59011(6) 0.51824(17) 0.0507(4) Uani 1 1 d . . . . .
N3 N 0.9205(3) 0.52309(6) 0.75648(16) 0.0358(4) Uani 1 1 d . . . . .
N1 N 0.7384(3) 0.46281(7) 0.90823(16) 0.0391(4) Uani 1 1 d . . . . .
H1 H 0.6311 0.4573 0.9694 0.047 Uiso 1 1 calc R . . . .
N41 N 1.2451(3) 0.49100(7) 0.62606(16) 0.0401(4) Uani 1 1 d . . . . .
H41A H 1.2589 0.5231 0.5923 0.048 Uiso 1 1 calc R . . . .
H41B H 1.3431 0.4646 0.6008 0.048 Uiso 1 1 calc R . . . .
O2 O 0.8132(4) 0.62549(7) 0.6494(2) 0.0698(6) Uani 1 1 d . . . . .
H2 H 0.8360 0.5935 0.6723 0.105 Uiso 1 1 calc GR . . . .
C4 C 1.0734(4) 0.48225(7) 0.71672(18) 0.0338(4) Uani 1 1 d . . . . .
C5 C 1.0545(4) 0.42927(8) 0.7736(2) 0.0370(4) Uani 1 1 d . . . . .
N4 N 0.3108(5) 0.84280(8) 0.3695(2) 0.0623(6) Uani 1 1 d . . . . .
H4A H 0.1856 0.8412 0.2979 0.075 Uiso 1 1 d GR . . . .
H4B H 0.4495 0.8687 0.3754 0.075 Uiso 1 1 d GR . . . .
C2 C 0.7517(4) 0.51409(8) 0.85384(19) 0.0352(4) Uani 1 1 d . . . . .
C6 C 0.8889(4) 0.42051(8) 0.8687(2) 0.0392(4) Uani 1 1 d . . . . .
H6 H 0.8768 0.3861 0.9071 0.047 Uiso 1 1 calc R . . . .
C7 C 0.5899(4) 0.62979(8) 0.5595(2) 0.0377(4) Uani 1 1 d . . . . .
C11 C 0.3849(4) 0.79077(8) 0.4142(2) 0.0428(5) Uani 1 1 d . U . . .
C8 C 0.5223(4) 0.68584(8) 0.51251(19) 0.0363(4) Uani 1 1 d . U . . .
C12' C 0.5433(13) 0.7832(2) 0.5374(6) 0.0410(12) Uani 0.45 1 d . U P A 2
H12' H 0.6118 0.8135 0.5876 0.049 Uiso 0.45 1 calc R . P A 2
C13' C 0.6034(11) 0.73211(19) 0.5886(5) 0.0377(10) Uani 0.45 1 d . U P A 2
H13' H 0.7001 0.7283 0.6757 0.045 Uiso 0.45 1 calc R . P A 2
C9 C 0.2685(9) 0.69536(17) 0.4420(5) 0.0459(9) Uani 0.55 1 d . U P A 1
H9 H 0.1450 0.6665 0.4237 0.055 Uiso 0.55 1 calc R . P A 1
C10 C 0.1905(10) 0.74713(17) 0.3968(5) 0.0496(9) Uani 0.55 1 d . U P A 1
H10 H 0.0108 0.7535 0.3551 0.059 Uiso 0.55 1 calc R . P A 1
C13 C 0.7116(10) 0.72911(17) 0.5354(5) 0.0483(10) Uani 0.55 1 d . . P A 1
H13 H 0.8878 0.7231 0.5818 0.058 Uiso 0.55 1 calc R . P A 1
C12 C 0.6350(12) 0.7806(2) 0.4889(6) 0.0516(12) Uani 0.55 1 d . . P A 1
H12 H 0.7582 0.8094 0.5091 0.062 Uiso 0.55 1 calc R . P A 1
C9' C 0.3671(10) 0.69338(19) 0.3839(5) 0.0363(10) Uani 0.45 1 d . . P A 2
H9' H 0.3032 0.6630 0.3327 0.044 Uiso 0.45 1 calc R . P A 2
C10' C 0.3078(10) 0.74454(18) 0.3321(5) 0.0389(10) Uani 0.45 1 d . . P A 2
H10' H 0.2175 0.7488 0.2437 0.047 Uiso 0.45 1 calc R . P A 2


_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 1.347(2) . ?
O21 C2 1.244(2) . ?
O3 C7 1.212(2) . ?
N3 C4 1.336(2) . ?
N3 C2 1.363(3) . ?
N1 H1 0.8600 . ?
N1 C2 1.371(2) . ?
N1 C6 1.356(3) . ?
N41 H41A 0.8600 . ?
N41 H41B 0.8600 . ?
N41 C4 1.321(3) . ?
O2 H2 0.8200 . ?
O2 C7 1.314(3) . ?
C4 C5 1.422(3) . ?
C5 C6 1.333(3) . ?
N4 H4A 0.8720 . ?
N4 H4B 0.9225 . ?
N4 C11 1.381(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.473(3) . ?
C11 C12' 1.365(7) . ?
C11 C10 1.423(5) . ?
C11 C12 1.361(6) . ?
C11 C10' 1.414(5) . ?
C8 C13' 1.388(5) . ?
C8 C9 1.357(5) . ?
C8 C13 1.403(5) . ?
C8 C9' 1.402(5) . ?
C12' H12' 0.9300 . ?
C12' C13' 1.367(8) . ?
C13' H13' 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.381(6) . ?
C10 H10 0.9300 . ?
C13 H13 0.9300 . ?
C13 C12 1.376(7) . ?
C12 H12 0.9300 . ?
C9' H9' 0.9300 . ?
C9' C10' 1.370(6) . ?
C10' H10' 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 119.82(16) . . ?
C2 N1 H1 118.9 . . ?
C6 N1 H1 118.9 . . ?
C6 N1 C2 122.13(17) . . ?
H41A N41 H41B 120.0 . . ?
C4 N41 H41A 120.0 . . ?
C4 N41 H41B 120.0 . . ?
C7 O2 H2 109.5 . . ?
N3 C4 C5 119.97(18) . . ?
N41 C4 N3 120.30(17) . . ?
N41 C4 C5 119.73(18) . . ?
F51 C5 C4 118.23(17) . . ?
C6 C5 F51 121.62(17) . . ?
C6 C5 C4 120.12(18) . . ?
H4A N4 H4B 120.8 . . ?
C11 N4 H4A 110.0 . . ?
C11 N4 H4B 117.1 . . ?
O21 C2 N3 121.25(17) . . ?
O21 C2 N1 119.49(18) . . ?
N3 C2 N1 119.26(17) . . ?
N1 C6 H6 120.7 . . ?
C5 C6 N1 118.69(18) . . ?
C5 C6 H6 120.7 . . ?
O3 C7 O2 121.65(19) . . ?
O3 C7 C8 123.59(19) . . ?
O2 C7 C8 114.75(17) . . ?
N4 C11 C10 120.9(3) . . ?
N4 C11 C10' 121.1(3) . . ?
C12' C11 N4 120.2(3) . . ?
C12' C11 C10' 118.6(3) . . ?
C12 C11 N4 121.3(3) . . ?
C12 C11 C10 117.5(3) . . ?
C13' C8 C7 123.7(3) . . ?
C13' C8 C9' 117.6(3) . . ?
C9 C8 C7 118.2(2) . . ?
C9 C8 C13 119.2(3) . . ?
C13 C8 C7 122.6(2) . . ?
C9' C8 C7 118.7(2) . . ?
C11 C12' H12' 119.3 . . ?
C11 C12' C13' 121.5(5) . . ?
C13' C12' H12' 119.3 . . ?
C8 C13' H13' 119.5 . . ?
C12' C13' C8 121.0(4) . . ?
C12' C13' H13' 119.5 . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.1(4) . . ?
C10 C9 H9 119.4 . . ?
C11 C10 H10 120.0 . . ?
C9 C10 C11 120.0(4) . . ?
C9 C10 H10 120.0 . . ?
C8 C13 H13 120.2 . . ?
C12 C13 C8 119.6(4) . . ?
C12 C13 H13 120.2 . . ?
C11 C12 C13 122.2(4) . . ?
C11 C12 H12 118.9 . . ?
C13 C12 H12 118.9 . . ?
C8 C9' H9' 119.3 . . ?
C10' C9' C8 121.4(4) . . ?
C10' C9' H9' 119.3 . . ?
C11 C10' H10' 120.3 . . ?
C9' C10' C11 119.4(4) . . ?
C9' C10' H10' 120.3 . . ?

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
F51 C5 C6 N1 178.54(17) . . . . ?
O3 C7 C8 C13' 155.9(3) . . . . ?
O3 C7 C8 C9 14.2(4) . . . . ?
O3 C7 C8 C13 -164.4(3) . . . . ?
O3 C7 C8 C9' -24.0(4) . . . . ?
N3 C4 C5 F51 -179.33(16) . . . . ?
N3 C4 C5 C6 -1.4(3) . . . . ?
N41 C4 C5 F51 -0.3(3) . . . . ?
N41 C4 C5 C6 177.66(18) . . . . ?
O2 C7 C8 C13' -25.3(4) . . . . ?
O2 C7 C8 C9 -166.9(3) . . . . ?
O2 C7 C8 C13 14.4(4) . . . . ?
O2 C7 C8 C9' 154.8(3) . . . . ?
C4 N3 C2 O21 179.01(17) . . . . ?
C4 N3 C2 N1 -0.9(3) . . . . ?
C4 C5 C6 N1 0.7(3) . . . . ?
N4 C11 C12' C13' 175.3(4) . . . . ?
N4 C11 C10 C9 179.9(4) . . . . ?
N4 C11 C12 C13 179.4(4) . . . . ?
N4 C11 C10' C9' -175.2(4) . . . . ?
C2 N3 C4 N41 -177.56(16) . . . . ?
C2 N3 C4 C5 1.5(3) . . . . ?
C2 N1 C6 C5 -0.1(3) . . . . ?
C6 N1 C2 O21 -179.72(18) . . . . ?
C6 N1 C2 N3 0.2(3) . . . . ?
C7 C8 C13' C12' 177.5(4) . . . . ?
C7 C8 C9 C10 179.0(4) . . . . ?
C7 C8 C13 C12 -179.9(4) . . . . ?
C7 C8 C9' C10' -177.2(4) . . . . ?
C11 C12' C13' C8 4.8(8) . . . . ?
C8 C9 C10 C11 5.2(7) . . . . ?
C8 C13 C12 C11 -3.6(8) . . . . ?
C8 C9' C10' C11 -5.2(7) . . . . ?
C12' C11 C10' C9' 7.1(7) . . . . ?
C13' C8 C9' C10' 2.9(7) . . . . ?
C9 C8 C13 C12 1.4(7) . . . . ?
C10 C11 C12 C13 6.2(7) . . . . ?
C13 C8 C9 C10 -2.3(7) . . . . ?
C12 C11 C10 C9 -6.9(6) . . . . ?
C9' C8 C13' C12' -2.6(7) . . . . ?
C10' C11 C12' C13' -6.9(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# 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_10830
_database_code_depnum_ccdc_archive 'CCDC 1817635'
_audit_update_record             
;
2018-07-17 deposited with the CCDC.
2018-07-26 downloaded from the CCDC.
;
_audit_creation_date             2017-08-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            '5-Fluorocytosine; 5-Flucytosine; 5-FC; 5FC-CA'
_chemical_name_systematic        '5-Fluorocytosine caprylic acid cocrystal'
_chemical_formula_moiety         'C4 H4 F N3 O, C8 H16 O2'
_chemical_formula_sum            'C12 H20 F N3 O3'
_chemical_formula_weight         273.31
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.2617(8)
_cell_length_b                   8.7066(14)
_cell_length_c                   15.710(2)
_cell_angle_alpha                81.892(3)
_cell_angle_beta                 85.884(3)
_cell_angle_gamma                84.460(3)
_cell_volume                     707.96(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5600
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      33.30
_cell_measurement_theta_min      2.55
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9456
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0606 before and 0.0439 after correction. The Ratio of minimum to maximum transmission is 0.9456. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.067
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            24416
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.550
_diffrn_reflns_theta_min         1.311
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3804
_reflns_number_total             5518
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.622
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.133
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         5518
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0560
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1220P)²+0.1090P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1817
_refine_ls_wR_factor_ref         0.2134
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B), C12(H12A,H12B),
 C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7)
2.c X=CH2 refined with riding coordinates:
 N41(H41A,H41B)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 1.07954(17) -0.06855(10) 0.68794(6) 0.0368(2) Uani 1 1 d . . . . .
O21 O 0.76264(18) 0.40684(10) 0.45726(6) 0.0295(2) Uani 1 1 d . . . . .
O3 O 0.4670(2) 0.64636(12) 0.29990(7) 0.0372(3) Uani 1 1 d . . . . .
O2 O 0.3881(2) 0.40634(12) 0.35633(8) 0.0453(3) Uani 1 1 d . . . . .
H2 H 0.5115 0.4132 0.3842 0.068 Uiso 1 1 calc GR . . . .
N3 N 0.71686(17) 0.15833(11) 0.52100(6) 0.0208(2) Uani 1 1 d . . . . .
N1 N 1.03323(18) 0.30530(11) 0.55985(6) 0.0225(2) Uani 1 1 d . . . . .
H1 H 1.1059 0.3909 0.5525 0.027 Uiso 1 1 calc R . . . .
N41 N 0.6828(2) -0.09074(12) 0.59034(7) 0.0274(2) Uani 1 1 d . . . . .
H41A H 0.5583 -0.1000 0.5594 0.033 Uiso 1 1 calc R . . . .
H41B H 0.7336 -0.1667 0.6282 0.033 Uiso 1 1 calc R . . . .
C4 C 0.7963(2) 0.04049(13) 0.57982(7) 0.0205(2) Uani 1 1 d . . . . .
C2 C 0.8329(2) 0.29235(13) 0.51112(7) 0.0209(2) Uani 1 1 d . . . . .
C5 C 1.0046(2) 0.05472(13) 0.63041(7) 0.0234(2) Uani 1 1 d . . . . .
C7 C 1.1213(2) 0.18677(14) 0.61959(8) 0.0239(2) Uani 1 1 d . . . . .
H7 H 1.2584 0.1973 0.6519 0.029 Uiso 1 1 calc R . . . .
C8 C 0.3505(2) 0.53391(15) 0.30076(8) 0.0274(3) Uani 1 1 d . . . . .
C9 C 0.1394(3) 0.52342(18) 0.24262(10) 0.0375(3) Uani 1 1 d . . . . .
H9A H 0.1642 0.4234 0.2213 0.045 Uiso 1 1 calc R . . . .
H9B H -0.0224 0.5271 0.2763 0.045 Uiso 1 1 calc R . . . .
C10 C 0.1236(3) 0.6499(2) 0.16694(10) 0.0444(4) Uani 1 1 d . . . . .
H10A H 0.2852 0.6458 0.1332 0.053 Uiso 1 1 calc R . . . .
H10B H 0.1000 0.7499 0.1882 0.053 Uiso 1 1 calc R . . . .
C11 C -0.0884(3) 0.6404(2) 0.10882(11) 0.0462(4) Uani 1 1 d . . . . .
H11A H -0.0733 0.5372 0.0915 0.055 Uiso 1 1 calc R . . . .
H11B H -0.2509 0.6535 0.1414 0.055 Uiso 1 1 calc R . . . .
C13 C -0.3046(4) 0.7603(3) -0.02917(11) 0.0568(5) Uani 1 1 d . . . . .
H13A H -0.3033 0.6575 -0.0463 0.068 Uiso 1 1 calc R . . . .
H13B H -0.4655 0.7807 0.0031 0.068 Uiso 1 1 calc R . . . .
C12 C -0.0911(4) 0.7583(3) 0.02951(12) 0.0617(6) Uani 1 1 d . . . . .
H12A H 0.0693 0.7416 -0.0037 0.074 Uiso 1 1 calc R . . . .
H12B H -0.0959 0.8608 0.0474 0.074 Uiso 1 1 calc R . . . .
C15 C -0.5138(5) 0.8888(5) -0.16558(14) 0.0927(11) Uani 1 1 d . . . . .
H15A H -0.4802 0.9601 -0.2167 0.139 Uiso 1 1 calc GR . . . .
H15B H -0.6679 0.9259 -0.1355 0.139 Uiso 1 1 calc GR . . . .
H15C H -0.5338 0.7881 -0.1811 0.139 Uiso 1 1 calc GR . . . .
C14 C -0.2956(5) 0.8768(4) -0.10863(15) 0.0882(9) Uani 1 1 d . . . . .
H14A H -0.2845 0.9785 -0.0913 0.106 Uiso 1 1 calc R . . . .
H14B H -0.1393 0.8520 -0.1425 0.106 Uiso 1 1 calc R . . . .


_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 1.3492(12) . ?
O21 C2 1.2579(13) . ?
O3 C8 1.2020(16) . ?
O2 H2 0.8200 . ?
O2 C8 1.3205(15) . ?
N3 C4 1.3366(13) . ?
N3 C2 1.3532(14) . ?
N1 H1 0.8600 . ?
N1 C2 1.3686(14) . ?
N1 C7 1.3629(14) . ?
N41 H41A 0.8600 . ?
N41 H41B 0.8600 . ?
N41 C4 1.3243(14) . ?
C4 C5 1.4237(15) . ?
C5 C7 1.3394(16) . ?
C7 H7 0.9300 . ?
C8 C9 1.5049(18) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.504(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.507(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.498(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C12 1.500(2) . ?
C13 C14 1.494(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C15 C14 1.493(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?

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
C8 O2 H2 109.5 . . ?
C4 N3 C2 119.42(9) . . ?
C2 N1 H1 119.0 . . ?
C7 N1 H1 119.0 . . ?
C7 N1 C2 122.08(9) . . ?
H41A N41 H41B 120.0 . . ?
C4 N41 H41A 120.0 . . ?
C4 N41 H41B 120.0 . . ?
N3 C4 C5 120.28(10) . . ?
N41 C4 N3 119.85(10) . . ?
N41 C4 C5 119.86(10) . . ?
O21 C2 N3 121.60(10) . . ?
O21 C2 N1 118.36(10) . . ?
N3 C2 N1 120.04(9) . . ?
F51 C5 C4 117.87(10) . . ?
C7 C5 F51 122.01(10) . . ?
C7 C5 C4 120.12(10) . . ?
N1 C7 H7 121.0 . . ?
C5 C7 N1 118.06(10) . . ?
C5 C7 H7 121.0 . . ?
O3 C8 O2 122.99(12) . . ?
O3 C8 C9 124.82(12) . . ?
O2 C8 C9 112.13(11) . . ?
C8 C9 H9A 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C10 C9 C8 114.39(12) . . ?
C10 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C9 C10 H10A 108.6 . . ?
C9 C10 H10B 108.6 . . ?
C9 C10 C11 114.58(14) . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C10 C11 H11A 108.6 . . ?
C10 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C12 C11 C10 114.65(17) . . ?
C12 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
H13A C13 H13B 107.4 . . ?
C12 C13 H13A 108.4 . . ?
C12 C13 H13B 108.4 . . ?
C14 C13 H13A 108.4 . . ?
C14 C13 H13B 108.4 . . ?
C14 C13 C12 115.6(2) . . ?
C11 C12 C13 117.46(19) . . ?
C11 C12 H12A 107.9 . . ?
C11 C12 H12B 107.9 . . ?
C13 C12 H12A 107.9 . . ?
C13 C12 H12B 107.9 . . ?
H12A C12 H12B 107.2 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
C13 C14 H14A 108.1 . . ?
C13 C14 H14B 108.1 . . ?
C15 C14 C13 116.9(2) . . ?
C15 C14 H14A 108.1 . . ?
C15 C14 H14B 108.1 . . ?
H14A C14 H14B 107.3 . . ?

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
F51 C5 C7 N1 179.84(11) . . . . ?
O3 C8 C9 C10 14.5(2) . . . . ?
O2 C8 C9 C10 -168.12(15) . . . . ?
N3 C4 C5 F51 -179.02(11) . . . . ?
N3 C4 C5 C7 0.35(18) . . . . ?
N41 C4 C5 F51 0.14(18) . . . . ?
N41 C4 C5 C7 179.51(12) . . . . ?
C4 N3 C2 O21 -179.19(11) . . . . ?
C4 N3 C2 N1 1.36(17) . . . . ?
C4 C5 C7 N1 0.49(19) . . . . ?
C2 N3 C4 N41 179.56(11) . . . . ?
C2 N3 C4 C5 -1.28(17) . . . . ?
C2 N1 C7 C5 -0.42(18) . . . . ?
C7 N1 C2 O21 -179.97(11) . . . . ?
C7 N1 C2 N3 -0.51(18) . . . . ?
C8 C9 C10 C11 -179.67(15) . . . . ?
C9 C10 C11 C12 -175.16(18) . . . . ?
C10 C11 C12 C13 -177.19(19) . . . . ?
C12 C13 C14 C15 -176.2(3) . . . . ?
C14 C13 C12 C11 -178.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
