# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

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

data_comp12
_database_code_depnum_ccdc_archive 'CCDC 1874345'
_audit_update_record             
;
2018-10-20 deposited with the CCDC.
2018-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H4 F N5 O6'
_chemical_formula_sum            'C5 H4 F N5 O6'
_chemical_formula_weight         249.13

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.976(3)
_cell_length_b                   8.218(3)
_cell_length_c                   15.344(6)
_cell_angle_alpha                94.059(8)
_cell_angle_beta                 104.850(7)
_cell_angle_gamma                97.364(8)
_cell_volume                     958.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3772
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      28.89

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.727
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.169
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14158
_diffrn_reflns_av_unetI/netI     0.0624
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.514
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4628
_reflns_number_gt                2968
_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       'APEX (Bruker, 2013)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material  
'SHELXL-2014/6 (Sheldrick, 2014) and PLATON (Spek, 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0406P)²+0.0448P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4628
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1034
_refine_ls_wR_factor_gt          0.0884
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.97363(15) 0.56961(14) 0.11787(8) 0.0267(3) Uani 1 1 d . . . . .
O1 O 1.2080(2) 0.8796(2) 0.27577(11) 0.0370(4) Uani 1 1 d . . . . .
O2 O 1.1824(2) 0.6128(2) 0.27332(10) 0.0337(4) Uani 1 1 d . . . . .
O3 O 1.2860(2) 0.87349(19) 0.09378(11) 0.0329(4) Uani 1 1 d . . . . .
O4 O 1.2290(2) 0.6108(2) 0.05022(11) 0.0348(4) Uani 1 1 d . . . . .
O5 O 0.8490(2) 0.77953(19) -0.21973(10) 0.0326(4) Uani 1 1 d . . . . .
O6 O 0.5738(2) 0.6733(2) -0.25797(10) 0.0367(4) Uani 1 1 d . . . . .
N1 N 0.8108(2) 0.8034(2) 0.03292(11) 0.0218(4) Uani 1 1 d . . . . .
N2 N 0.8595(2) 0.8034(2) -0.04490(11) 0.0204(4) Uani 1 1 d . . . . .
N3 N 1.1594(2) 0.7392(2) 0.23926(12) 0.0244(4) Uani 1 1 d . . . . .
N4 N 1.2051(2) 0.7358(2) 0.08853(11) 0.0226(4) Uani 1 1 d . . . . .
N5 N 0.7109(2) 0.7320(2) -0.20122(12) 0.0251(4) Uani 1 1 d . . . . .
C1 C 0.7108(3) 0.7462(3) -0.10682(13) 0.0222(5) Uani 1 1 d . . . . .
C2 C 0.5669(3) 0.7091(3) -0.07179(14) 0.0278(5) Uani 1 1 d . . . . .
H2 H 0.4487 0.6675 -0.1037 0.033 Uiso 1 1 calc R U . . .
C3 C 0.6378(3) 0.7474(3) 0.01979(14) 0.0273(5) Uani 1 1 d . . . . .
H3 H 0.5772 0.7368 0.0654 0.033 Uiso 1 1 calc R U . . .
C4 C 0.9434(3) 0.8535(3) 0.11842(13) 0.0209(4) Uani 1 1 d . . . . .
H4A H 0.8862 0.8704 0.1678 0.025 Uiso 1 1 calc R U . . .
H4B H 1.0155 0.9589 0.1148 0.025 Uiso 1 1 calc R U . . .
C5 C 1.0592(3) 0.7211(2) 0.13848(13) 0.0197(4) Uani 1 1 d . . . . .
F1' F -0.00661(15) 0.05955(14) 0.36657(8) 0.0274(3) Uani 1 1 d . . . . .
O1' O -0.1949(2) 0.3305(2) 0.24319(11) 0.0386(4) Uani 1 1 d . . . . .
O2' O -0.2923(2) 0.0712(2) 0.24113(12) 0.0451(5) Uani 1 1 d . . . . .
O3' O -0.27392(19) 0.29783(19) 0.43873(11) 0.0321(4) Uani 1 1 d . . . . .
O4' O -0.2021(2) 0.0587(2) 0.47235(11) 0.0359(4) Uani 1 1 d . . . . .
O5' O 0.1915(2) 0.3168(2) 0.73414(10) 0.0335(4) Uani 1 1 d . . . . .
O6' O 0.46460(19) 0.2873(2) 0.75789(10) 0.0308(4) Uani 1 1 d . . . . .
N1' N 0.1945(2) 0.3312(2) 0.47623(11) 0.0193(4) Uani 1 1 d . . . . .
N2' N 0.1593(2) 0.3334(2) 0.55799(11) 0.0202(4) Uani 1 1 d . . . . .
N3' N -0.1995(2) 0.2007(2) 0.27532(12) 0.0274(4) Uani 1 1 d . . . . .
N4' N -0.1954(2) 0.1811(2) 0.43323(12) 0.0245(4) Uani 1 1 d . . . . .
N5' N 0.3229(2) 0.3045(2) 0.70787(11) 0.0232(4) Uani 1 1 d . . . . .
C1' C 0.3100(3) 0.3103(2) 0.61239(13) 0.0198(4) Uani 1 1 d . . . . .
C2' C 0.4407(3) 0.2913(3) 0.56869(13) 0.0238(5) Uani 1 1 d . . . . .
H2' H 0.5576 0.2733 0.5944 0.029 Uiso 1 1 calc R U . . .
C3' C 0.3603(3) 0.3047(3) 0.48000(14) 0.0234(5) Uani 1 1 d . . . . .
H3' H 0.4110 0.2970 0.4305 0.028 Uiso 1 1 calc R U . . .
C4' C 0.0587(3) 0.3515(2) 0.39639(13) 0.0204(4) Uani 1 1 d . . . . .
H4'A H 0.1116 0.3742 0.3459 0.025 Uiso 1 1 calc R U . . .
H4'B H 0.0008 0.4466 0.4092 0.025 Uiso 1 1 calc R U . . .
C5' C -0.0750(3) 0.1975(3) 0.36933(13) 0.0208(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C5 1.316(2) . ?
O1 N3 1.216(2) . ?
O2 N3 1.209(2) . ?
O3 N4 1.215(2) . ?
O4 N4 1.208(2) . ?
O5 N5 1.230(2) . ?
O6 N5 1.227(2) . ?
N1 N2 1.347(2) . ?
N1 C3 1.355(3) . ?
N1 C4 1.453(3) . ?
N2 C1 1.322(3) . ?
N3 C5 1.535(3) . ?
N4 C5 1.546(3) . ?
N5 C1 1.445(3) . ?
C1 C2 1.396(3) . ?
C2 C3 1.370(3) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 C5 1.513(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
F1' C5' 1.322(2) . ?
O1' N3' 1.206(2) . ?
O2' N3' 1.215(2) . ?
O3' N4' 1.221(2) . ?
O4' N4' 1.210(2) . ?
O5' N5' 1.228(2) . ?
O6' N5' 1.224(2) . ?
N1' N2' 1.353(2) . ?
N1' C3' 1.355(3) . ?
N1' C4' 1.448(3) . ?
N2' C1' 1.321(3) . ?
N3' C5' 1.532(3) . ?
N4' C5' 1.539(3) . ?
N5' C1' 1.447(3) . ?
C1' C2' 1.395(3) . ?
C2' C3' 1.366(3) . ?
C2' H2' 0.9500 . ?
C3' H3' 0.9500 . ?
C4' C5' 1.504(3) . ?
C4' H4'A 0.9900 . ?
C4' H4'B 0.9900 . ?

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
N2 N1 C3 113.01(17) . . ?
N2 N1 C4 118.97(16) . . ?
C3 N1 C4 127.95(17) . . ?
C1 N2 N1 102.60(16) . . ?
O2 N3 O1 127.27(18) . . ?
O2 N3 C5 116.61(17) . . ?
O1 N3 C5 116.12(17) . . ?
O4 N4 O3 126.99(18) . . ?
O4 N4 C5 117.41(17) . . ?
O3 N4 C5 115.58(16) . . ?
O6 N5 O5 123.96(18) . . ?
O6 N5 C1 118.18(18) . . ?
O5 N5 C1 117.86(17) . . ?
N2 C1 C2 114.32(18) . . ?
N2 C1 N5 118.63(18) . . ?
C2 C1 N5 127.03(19) . . ?
C3 C2 C1 103.07(19) . . ?
C3 C2 H2 128.5 . . ?
C1 C2 H2 128.5 . . ?
N1 C3 C2 107.00(18) . . ?
N1 C3 H3 126.5 . . ?
C2 C3 H3 126.5 . . ?
N1 C4 C5 109.41(16) . . ?
N1 C4 H4A 109.8 . . ?
C5 C4 H4A 109.8 . . ?
N1 C4 H4B 109.8 . . ?
C5 C4 H4B 109.8 . . ?
H4A C4 H4B 108.2 . . ?
F1 C5 C4 114.02(16) . . ?
F1 C5 N3 107.42(16) . . ?
C4 C5 N3 111.02(16) . . ?
F1 C5 N4 107.47(15) . . ?
C4 C5 N4 112.16(16) . . ?
N3 C5 N4 104.17(15) . . ?
N2' N1' C3' 112.97(16) . . ?
N2' N1' C4' 119.82(16) . . ?
C3' N1' C4' 127.19(17) . . ?
C1' N2' N1' 102.46(15) . . ?
O1' N3' O2' 127.08(19) . . ?
O1' N3' C5' 116.91(18) . . ?
O2' N3' C5' 116.01(18) . . ?
O4' N4' O3' 127.17(18) . . ?
O4' N4' C5' 118.50(17) . . ?
O3' N4' C5' 114.32(17) . . ?
O6' N5' O5' 123.75(17) . . ?
O6' N5' C1' 117.87(17) . . ?
O5' N5' C1' 118.38(17) . . ?
N2' C1' C2' 114.23(18) . . ?
N2' C1' N5' 118.56(17) . . ?
C2' C1' N5' 127.20(18) . . ?
C3' C2' C1' 103.45(18) . . ?
C3' C2' H2' 128.3 . . ?
C1' C2' H2' 128.3 . . ?
N1' C3' C2' 106.88(18) . . ?
N1' C3' H3' 126.6 . . ?
C2' C3' H3' 126.6 . . ?
N1' C4' C5' 109.98(16) . . ?
N1' C4' H4'A 109.7 . . ?
C5' C4' H4'A 109.7 . . ?
N1' C4' H4'B 109.7 . . ?
C5' C4' H4'B 109.7 . . ?
H4'A C4' H4'B 108.2 . . ?
F1' C5' C4' 114.14(17) . . ?
F1' C5' N3' 106.68(16) . . ?
C4' C5' N3' 111.35(16) . . ?
F1' C5' N4' 107.46(16) . . ?
C4' C5' N4' 111.89(16) . . ?
N3' C5' N4' 104.73(15) . . ?

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
C3 N1 N2 C1 0.3(2) . . . . ?
C4 N1 N2 C1 177.53(17) . . . . ?
N1 N2 C1 C2 0.0(2) . . . . ?
N1 N2 C1 N5 178.58(17) . . . . ?
O6 N5 C1 N2 177.44(18) . . . . ?
O5 N5 C1 N2 -2.5(3) . . . . ?
O6 N5 C1 C2 -4.2(3) . . . . ?
O5 N5 C1 C2 175.9(2) . . . . ?
N2 C1 C2 C3 -0.3(3) . . . . ?
N5 C1 C2 C3 -178.7(2) . . . . ?
N2 N1 C3 C2 -0.5(3) . . . . ?
C4 N1 C3 C2 -177.43(19) . . . . ?
C1 C2 C3 N1 0.5(2) . . . . ?
N2 N1 C4 C5 -71.5(2) . . . . ?
C3 N1 C4 C5 105.3(2) . . . . ?
N1 C4 C5 F1 -39.9(2) . . . . ?
N1 C4 C5 N3 -161.43(15) . . . . ?
N1 C4 C5 N4 82.5(2) . . . . ?
O2 N3 C5 F1 18.9(2) . . . . ?
O1 N3 C5 F1 -161.52(17) . . . . ?
O2 N3 C5 C4 144.23(18) . . . . ?
O1 N3 C5 C4 -36.2(2) . . . . ?
O2 N3 C5 N4 -94.86(19) . . . . ?
O1 N3 C5 N4 84.7(2) . . . . ?
O4 N4 C5 F1 -7.9(2) . . . . ?
O3 N4 C5 F1 173.38(17) . . . . ?
O4 N4 C5 C4 -134.02(18) . . . . ?
O3 N4 C5 C4 47.3(2) . . . . ?
O4 N4 C5 N3 105.83(19) . . . . ?
O3 N4 C5 N3 -72.8(2) . . . . ?
C3' N1' N2' C1' 1.0(2) . . . . ?
C4' N1' N2' C1' 179.44(17) . . . . ?
N1' N2' C1' C2' -0.7(2) . . . . ?
N1' N2' C1' N5' -179.76(17) . . . . ?
O6' N5' C1' N2' -178.14(18) . . . . ?
O5' N5' C1' N2' 2.0(3) . . . . ?
O6' N5' C1' C2' 2.9(3) . . . . ?
O5' N5' C1' C2' -176.9(2) . . . . ?
N2' C1' C2' C3' 0.1(2) . . . . ?
N5' C1' C2' C3' 179.1(2) . . . . ?
N2' N1' C3' C2' -1.0(2) . . . . ?
C4' N1' C3' C2' -179.26(19) . . . . ?
C1' C2' C3' N1' 0.5(2) . . . . ?
N2' N1' C4' C5' -73.0(2) . . . . ?
C3' N1' C4' C5' 105.1(2) . . . . ?
N1' C4' C5' F1' -47.8(2) . . . . ?
N1' C4' C5' N3' -168.66(15) . . . . ?
N1' C4' C5' N4' 74.5(2) . . . . ?
O1' N3' C5' F1' -137.06(18) . . . . ?
O2' N3' C5' F1' 42.8(2) . . . . ?
O1' N3' C5' C4' -11.9(2) . . . . ?
O2' N3' C5' C4' 167.95(18) . . . . ?
O1' N3' C5' N4' 109.2(2) . . . . ?
O2' N3' C5' N4' -70.9(2) . . . . ?
O4' N4' C5' F1' 3.7(2) . . . . ?
O3' N4' C5' F1' -176.77(16) . . . . ?
O4' N4' C5' C4' -122.3(2) . . . . ?
O3' N4' C5' C4' 57.2(2) . . . . ?
O4' N4' C5' N3' 116.92(19) . . . . ?
O3' N4' C5' N3' -63.6(2) . . . . ?

_refine_diff_density_max         0.279
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.057

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_comp13
_database_code_depnum_ccdc_archive 'CCDC 1874346'
_audit_update_record             
;
2018-10-20 deposited with the CCDC.
2018-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H4 F N5 O6'
_chemical_formula_sum            'C5 H4 F N5 O6'
_chemical_formula_weight         249.13

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   5.4659(12)
_cell_length_b                   10.477(2)
_cell_length_c                   8.1322(17)
_cell_angle_alpha                90
_cell_angle_beta                 94.857(4)
_cell_angle_gamma                90
_cell_volume                     464.02(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    817
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      24.02

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.783
_exptl_crystal_F_000             252
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.174
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4928
_diffrn_reflns_av_unetI/netI     0.0818
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.514
_diffrn_reflns_theta_max         27.148
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2039
_reflns_number_gt                1475
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.890
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    1.000

_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       'APEX (Bruker, 2013)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material  
'SHELXL-2014/6 (Sheldrick, 2014) and PLATON (Spek, 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0235P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 556 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(10)
_chemical_absolute_configuration Unk
_refine_ls_number_reflns         2039
_refine_ls_number_parameters     154
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.0781
_refine_ls_wR_factor_gt          0.0688
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_restrained_S_all      0.987
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.1058(4) -0.8387(2) -0.9350(3) 0.0223(6) Uani 1 1 d . . . . .
O1 O -0.6396(5) -0.6706(3) -0.9394(4) 0.0286(8) Uani 1 1 d . . . . .
O2 O -0.5391(6) -0.8639(3) -0.8614(4) 0.0317(8) Uani 1 1 d . . . . .
O3 O -0.1170(6) -0.5261(3) -0.8815(3) 0.0246(7) Uani 1 1 d . . . . .
O4 O -0.1076(6) -0.6737(3) -0.6932(3) 0.0284(8) Uani 1 1 d . . . . .
O5 O 0.0498(6) -0.9764(3) -1.6182(3) 0.0273(8) Uani 1 1 d . . . . .
O6 O -0.2919(6) -1.0845(3) -1.6315(4) 0.0300(8) Uani 1 1 d . . . . .
N1 N -0.2701(6) -0.7816(3) -1.2553(4) 0.0172(8) Uani 1 1 d . . . . .
N2 N -0.4877(6) -0.8471(3) -1.2606(4) 0.0209(8) Uani 1 1 d . . . . .
N3 N -0.4971(7) -0.7613(4) -0.9181(4) 0.0203(8) Uani 1 1 d . . . . .
N4 N -0.1424(6) -0.6348(3) -0.8333(4) 0.0174(8) Uani 1 1 d . . . . .
N5 N -0.1571(7) -0.9973(3) -1.5739(4) 0.0236(9) Uani 1 1 d . . . . .
C1 C -0.4690(8) -0.9318(4) -1.3792(5) 0.0211(10) Uani 1 1 d . . . . .
H1 H -0.5923 -0.9923 -1.4137 0.025 Uiso 1 1 calc R U . . .
C2 C -0.2443(8) -0.9205(4) -1.4470(5) 0.0190(9) Uani 1 1 d . . . . .
C3 C -0.1191(7) -0.8231(4) -1.3636(5) 0.0171(9) Uani 1 1 d . . . . .
H3 H 0.0405 -0.7922 -1.3798 0.021 Uiso 1 1 calc R U . . .
C4 C -0.2257(8) -0.6798(4) -1.1359(5) 0.0183(9) Uani 1 1 d . . . . .
H4A H -0.3520 -0.6125 -1.1560 0.022 Uiso 1 1 calc R U . . .
H4B H -0.0628 -0.6411 -1.1475 0.022 Uiso 1 1 calc R U . . .
C5 C -0.2345(7) -0.7329(4) -0.9641(5) 0.0171(9) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C5 1.323(5) . ?
O1 N3 1.232(4) . ?
O2 N3 1.200(5) . ?
O3 N4 1.216(4) . ?
O4 N4 1.210(4) . ?
O5 N5 1.235(4) . ?
O6 N5 1.241(5) . ?
N1 C3 1.330(5) . ?
N1 N2 1.371(4) . ?
N1 C4 1.449(5) . ?
N2 C1 1.321(5) . ?
N3 C5 1.543(5) . ?
N4 C5 1.533(5) . ?
N5 C2 1.422(5) . ?
C1 C2 1.393(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.375(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.508(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?

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
C3 N1 N2 113.7(3) . . ?
C3 N1 C4 127.3(4) . . ?
N2 N1 C4 119.0(3) . . ?
C1 N2 N1 103.8(3) . . ?
O2 N3 O1 127.3(4) . . ?
O2 N3 C5 118.6(4) . . ?
O1 N3 C5 114.0(3) . . ?
O4 N4 O3 127.3(4) . . ?
O4 N4 C5 116.3(3) . . ?
O3 N4 C5 116.3(3) . . ?
O5 N5 O6 123.3(4) . . ?
O5 N5 C2 118.9(3) . . ?
O6 N5 C2 117.8(4) . . ?
N2 C1 C2 110.9(4) . . ?
N2 C1 H1 124.5 . . ?
C2 C1 H1 124.5 . . ?
C3 C2 C1 106.7(4) . . ?
C3 C2 N5 126.4(4) . . ?
C1 C2 N5 126.9(4) . . ?
N1 C3 C2 105.0(4) . . ?
N1 C3 H3 127.5 . . ?
C2 C3 H3 127.5 . . ?
N1 C4 C5 109.4(3) . . ?
N1 C4 H4A 109.8 . . ?
C5 C4 H4A 109.8 . . ?
N1 C4 H4B 109.8 . . ?
C5 C4 H4B 109.8 . . ?
H4A C4 H4B 108.2 . . ?
F1 C5 C4 114.6(3) . . ?
F1 C5 N4 107.4(3) . . ?
C4 C5 N4 111.2(3) . . ?
F1 C5 N3 106.6(3) . . ?
C4 C5 N3 113.5(3) . . ?
N4 C5 N3 102.6(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
C3 N1 N2 C1 -0.7(4) . . . . ?
C4 N1 N2 C1 -179.6(3) . . . . ?
N1 N2 C1 C2 0.2(4) . . . . ?
N2 C1 C2 C3 0.2(5) . . . . ?
N2 C1 C2 N5 178.3(4) . . . . ?
O5 N5 C2 C3 -0.8(6) . . . . ?
O6 N5 C2 C3 177.3(4) . . . . ?
O5 N5 C2 C1 -178.6(4) . . . . ?
O6 N5 C2 C1 -0.4(6) . . . . ?
N2 N1 C3 C2 0.8(4) . . . . ?
C4 N1 C3 C2 179.6(3) . . . . ?
C1 C2 C3 N1 -0.6(4) . . . . ?
N5 C2 C3 N1 -178.7(4) . . . . ?
C3 N1 C4 C5 -118.8(4) . . . . ?
N2 N1 C4 C5 60.0(4) . . . . ?
N1 C4 C5 F1 47.5(4) . . . . ?
N1 C4 C5 N4 169.5(3) . . . . ?
N1 C4 C5 N3 -75.3(4) . . . . ?
O4 N4 C5 F1 -43.3(5) . . . . ?
O3 N4 C5 F1 138.0(3) . . . . ?
O4 N4 C5 C4 -169.4(3) . . . . ?
O3 N4 C5 C4 11.9(5) . . . . ?
O4 N4 C5 N3 68.9(4) . . . . ?
O3 N4 C5 N3 -109.8(4) . . . . ?
O2 N3 C5 F1 2.9(5) . . . . ?
O1 N3 C5 F1 -179.8(3) . . . . ?
O2 N3 C5 C4 130.0(4) . . . . ?
O1 N3 C5 C4 -52.7(5) . . . . ?
O2 N3 C5 N4 -109.9(4) . . . . ?
O1 N3 C5 N4 67.4(4) . . . . ?

_refine_diff_density_max         0.218
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.054

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_comp28
_database_code_depnum_ccdc_archive 'CCDC 1874347'
_audit_update_record             
;
2018-10-20 deposited with the CCDC.
2018-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H3 F N6 O4'
_chemical_formula_sum            'C3 H3 F N6 O4'
_chemical_formula_weight         206.11

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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.4331(11)
_cell_length_b                   5.7212(6)
_cell_length_c                   11.2434(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     735.44(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2339
_cell_measurement_theta_min      3.56
_cell_measurement_theta_max      27.81

_exptl_crystal_description       prizm
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.862
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.182
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7221
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.564
_diffrn_reflns_theta_max         28.920
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1930
_reflns_number_gt                1773
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.903
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.998

_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       'APEX (Bruker, 2013)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material  
'SHELXL-2014/6 (Sheldrick, 2014) and PLATON (Spek, 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0343P)²+0.0120P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 780 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1930
_refine_ls_number_parameters     127
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_ref         0.0648
_refine_ls_wR_factor_gt          0.0628
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.01885(10) 0.2493(2) 0.98105(12) 0.0181(3) Uani 1 1 d . . . . .
O1 O 0.06999(16) 0.3699(3) 1.19109(15) 0.0286(4) Uani 1 1 d . . . . .
O2 O -0.02123(14) 0.0717(3) 1.26724(15) 0.0258(4) Uani 1 1 d . . . . .
O3 O -0.06505(14) -0.2801(3) 1.03529(15) 0.0239(4) Uani 1 1 d . . . . .
O4 O 0.11405(13) -0.1500(3) 1.04911(16) 0.0255(4) Uani 1 1 d . . . . .
N1 N -0.21097(14) 0.1275(3) 0.93820(14) 0.0116(3) Uani 1 1 d . . . . .
N2 N -0.22441(15) 0.3243(3) 0.87158(16) 0.0157(4) Uani 1 1 d . . . . .
N3 N -0.26402(14) 0.2559(3) 0.77049(17) 0.0176(4) Uani 1 1 d . . . . .
N4 N -0.27780(14) 0.0184(3) 0.76753(16) 0.0178(4) Uani 1 1 d . . . . .
N5 N 0.00979(15) 0.1970(3) 1.18567(16) 0.0162(4) Uani 1 1 d . . . . .
N6 N 0.00783(15) -0.1278(3) 1.04816(16) 0.0164(4) Uani 1 1 d . . . . .
C1 C -0.24381(17) -0.0560(4) 0.87249(18) 0.0152(4) Uani 1 1 d . . . . .
H1 H -0.2427 -0.2145 0.8977 0.018 Uiso 1 1 calc R U . . .
C2 C -0.16816(16) 0.1451(3) 1.05957(17) 0.0124(4) Uani 1 1 d . . . . .
H2A H -0.2033 0.0195 1.1085 0.015 Uiso 1 1 calc R U . . .
H2B H -0.1919 0.2973 1.0939 0.015 Uiso 1 1 calc R U . . .
C3 C -0.03596(16) 0.1241(3) 1.06266(18) 0.0129(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C3 1.322(2) . ?
O1 N5 1.206(2) . ?
O2 N5 1.217(3) . ?
O3 N6 1.214(2) . ?
O4 N6 1.221(2) . ?
N1 C1 1.337(3) . ?
N1 N2 1.361(2) . ?
N1 C2 1.453(2) . ?
N2 N3 1.285(3) . ?
N3 N4 1.368(3) . ?
N4 C1 1.313(3) . ?
N5 C3 1.536(3) . ?
N6 C3 1.534(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.517(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?

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
C1 N1 N2 108.28(16) . . ?
C1 N1 C2 131.89(17) . . ?
N2 N1 C2 119.83(16) . . ?
N3 N2 N1 105.96(17) . . ?
N2 N3 N4 111.37(18) . . ?
C1 N4 N3 105.43(18) . . ?
O1 N5 O2 127.67(19) . . ?
O1 N5 C3 117.55(17) . . ?
O2 N5 C3 114.77(16) . . ?
O3 N6 O4 127.51(18) . . ?
O3 N6 C3 117.57(16) . . ?
O4 N6 C3 114.91(16) . . ?
N4 C1 N1 108.97(19) . . ?
N4 C1 H1 125.5 . . ?
N1 C1 H1 125.5 . . ?
N1 C2 C3 110.58(15) . . ?
N1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
F1 C3 C2 114.43(16) . . ?
F1 C3 N6 106.29(15) . . ?
C2 C3 N6 113.42(15) . . ?
F1 C3 N5 108.42(15) . . ?
C2 C3 N5 109.77(15) . . ?
N6 C3 N5 103.87(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
C1 N1 N2 N3 0.1(2) . . . . ?
C2 N1 N2 N3 -179.33(16) . . . . ?
N1 N2 N3 N4 0.1(2) . . . . ?
N2 N3 N4 C1 -0.3(2) . . . . ?
N3 N4 C1 N1 0.4(2) . . . . ?
N2 N1 C1 N4 -0.3(2) . . . . ?
C2 N1 C1 N4 179.03(18) . . . . ?
C1 N1 C2 C3 89.6(2) . . . . ?
N2 N1 C2 C3 -91.1(2) . . . . ?
N1 C2 C3 F1 45.3(2) . . . . ?
N1 C2 C3 N6 -76.9(2) . . . . ?
N1 C2 C3 N5 167.42(15) . . . . ?
O3 N6 C3 F1 -126.12(19) . . . . ?
O4 N6 C3 F1 52.7(2) . . . . ?
O3 N6 C3 C2 0.5(2) . . . . ?
O4 N6 C3 C2 179.31(17) . . . . ?
O3 N6 C3 N5 119.59(19) . . . . ?
O4 N6 C3 N5 -61.6(2) . . . . ?
O1 N5 C3 F1 11.0(2) . . . . ?
O2 N5 C3 F1 -169.86(17) . . . . ?
O1 N5 C3 C2 -114.7(2) . . . . ?
O2 N5 C3 C2 64.5(2) . . . . ?
O1 N5 C3 N6 123.74(19) . . . . ?
O2 N5 C3 N6 -57.1(2) . . . . ?

_refine_diff_density_max         0.202
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.047

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_comp21
_database_code_depnum_ccdc_archive 'CCDC 1874348'
_audit_update_record             
;
2018-10-20 deposited with the CCDC.
2018-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H4 F N5 O6'
_chemical_formula_sum            'C5 H4 F N5 O6'
_chemical_formula_weight         249.13

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   6.6055(3)
_cell_length_b                   11.5186(5)
_cell_length_c                   23.4809(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1786.57(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7464
_cell_measurement_theta_min      3.47
_cell_measurement_theta_max      30.08

_exptl_crystal_description       prizm
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.852
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.181
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22344
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.471
_diffrn_reflns_theta_max         30.076
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2621
_reflns_number_gt                2288
_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       'APEX (Bruker, 2013)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material  
'SHELXL-2014/6 (Sheldrick, 2014) and PLATON (Spek, 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0462P)²+0.6922P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2621
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0878
_refine_ls_wR_factor_gt          0.0837
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.13584(10) 0.18956(6) 0.02855(3) 0.01933(15) Uani 1 1 d . . . . .
O1 O 0.37539(13) 0.17734(8) 0.15192(4) 0.02454(19) Uani 1 1 d . . . . .
O2 O 0.50351(13) 0.17707(8) 0.06603(4) 0.0270(2) Uani 1 1 d . . . . .
O3 O 0.19448(14) -0.07171(7) 0.09466(4) 0.02311(18) Uani 1 1 d . . . . .
O4 O 0.22622(16) -0.01743(8) 0.00612(4) 0.0296(2) Uani 1 1 d . . . . .
O5 O -0.07406(14) 0.44500(7) 0.27947(3) 0.02230(18) Uani 1 1 d . . . . .
O6 O -0.18678(13) 0.58098(7) 0.22327(4) 0.02142(18) Uani 1 1 d . . . . .
N1 N -0.05242(13) 0.25062(7) 0.13441(3) 0.01229(17) Uani 1 1 d . . . . .
N2 N -0.15761(14) 0.43451(8) 0.13088(4) 0.01600(18) Uani 1 1 d . . . . .
N3 N 0.36757(13) 0.16408(7) 0.10077(4) 0.01628(18) Uani 1 1 d . . . . .
N4 N 0.19759(13) -0.00019(8) 0.05658(4) 0.01600(17) Uani 1 1 d . . . . .
N5 N -0.12298(13) 0.48218(8) 0.23211(4) 0.01552(18) Uani 1 1 d . . . . .
C1 C -0.12624(15) 0.33937(8) 0.10126(4) 0.01496(19) Uani 1 1 d . . . . .
H1 H -0.1516 0.3327 0.0616 0.018 Uiso 1 1 calc R U . . .
C2 C -0.10378(15) 0.40341(8) 0.18509(4) 0.01359(18) Uani 1 1 d . . . . .
C3 C -0.03770(15) 0.29134(8) 0.18905(4) 0.01350(18) Uani 1 1 d . . . . .
H3 H 0.0078 0.2511 0.2220 0.016 Uiso 1 1 calc R U . . .
C4 C -0.01225(15) 0.13187(8) 0.11678(4) 0.01283(18) Uani 1 1 d . . . . .
H4A H -0.1347 0.0992 0.0985 0.015 Uiso 1 1 calc R U . . .
H4B H 0.0191 0.0841 0.1507 0.015 Uiso 1 1 calc R U . . .
C5 C 0.16315(15) 0.12615(8) 0.07548(4) 0.01301(18) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C5 1.3344(11) . ?
O1 N3 1.2118(13) . ?
O2 N3 1.2224(12) . ?
O3 N4 1.2159(12) . ?
O4 N4 1.2162(12) . ?
O5 N5 1.2347(12) . ?
O6 N5 1.2312(12) . ?
N1 C3 1.3694(12) . ?
N1 C1 1.3743(12) . ?
N1 C4 1.4535(12) . ?
N2 C1 1.3143(13) . ?
N2 C2 1.3695(13) . ?
N3 C5 1.5385(13) . ?
N4 C5 1.5383(13) . ?
N5 C2 1.4347(12) . ?
C1 H1 0.9500 . ?
C2 C3 1.3658(13) . ?
C3 H3 0.9500 . ?
C4 C5 1.5123(13) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?

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
C3 N1 C1 107.52(8) . . ?
C3 N1 C4 125.19(8) . . ?
C1 N1 C4 127.11(8) . . ?
C1 N2 C2 103.46(8) . . ?
O1 N3 O2 127.93(10) . . ?
O1 N3 C5 117.12(8) . . ?
O2 N3 C5 114.95(9) . . ?
O3 N4 O4 127.47(9) . . ?
O3 N4 C5 115.23(8) . . ?
O4 N4 C5 117.29(9) . . ?
O6 N5 O5 124.20(9) . . ?
O6 N5 C2 119.02(9) . . ?
O5 N5 C2 116.79(8) . . ?
N2 C1 N1 112.12(9) . . ?
N2 C1 H1 123.9 . . ?
N1 C1 H1 123.9 . . ?
C3 C2 N2 113.17(9) . . ?
C3 C2 N5 125.00(9) . . ?
N2 C2 N5 121.81(9) . . ?
C2 C3 N1 103.73(8) . . ?
C2 C3 H3 128.1 . . ?
N1 C3 H3 128.1 . . ?
N1 C4 C5 111.32(8) . . ?
N1 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
N1 C4 H4B 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
F1 C5 C4 113.71(8) . . ?
F1 C5 N4 107.43(8) . . ?
C4 C5 N4 109.85(8) . . ?
F1 C5 N3 106.38(8) . . ?
C4 C5 N3 114.36(8) . . ?
N4 C5 N3 104.49(7) . . ?

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
C2 N2 C1 N1 -0.87(12) . . . . ?
C3 N1 C1 N2 0.71(12) . . . . ?
C4 N1 C1 N2 175.98(9) . . . . ?
C1 N2 C2 C3 0.75(12) . . . . ?
C1 N2 C2 N5 -177.50(9) . . . . ?
O6 N5 C2 C3 -179.13(10) . . . . ?
O5 N5 C2 C3 0.58(15) . . . . ?
O6 N5 C2 N2 -1.10(14) . . . . ?
O5 N5 C2 N2 178.61(10) . . . . ?
N2 C2 C3 N1 -0.33(11) . . . . ?
N5 C2 C3 N1 177.85(9) . . . . ?
C1 N1 C3 C2 -0.21(11) . . . . ?
C4 N1 C3 C2 -175.59(9) . . . . ?
C3 N1 C4 C5 -117.52(10) . . . . ?
C1 N1 C4 C5 68.00(12) . . . . ?
N1 C4 C5 F1 -58.10(11) . . . . ?
N1 C4 C5 N4 -178.52(8) . . . . ?
N1 C4 C5 N3 64.38(10) . . . . ?
O3 N4 C5 F1 -169.35(9) . . . . ?
O4 N4 C5 F1 11.25(12) . . . . ?
O3 N4 C5 C4 -45.19(11) . . . . ?
O4 N4 C5 C4 135.41(10) . . . . ?
O3 N4 C5 N3 77.92(10) . . . . ?
O4 N4 C5 N3 -101.48(10) . . . . ?
O1 N3 C5 F1 137.22(9) . . . . ?
O2 N3 C5 F1 -42.84(11) . . . . ?
O1 N3 C5 C4 10.84(12) . . . . ?
O2 N3 C5 C4 -169.23(8) . . . . ?
O1 N3 C5 N4 -109.30(10) . . . . ?
O2 N3 C5 N4 70.64(10) . . . . ?

_refine_diff_density_max         0.393
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.050

_shelxl_version_number           2014/6



