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

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1540466'
_audit_update_record             
;
2017-03-27 deposited with the CCDC.
2018-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H5 F N6 O4'
_chemical_formula_sum            'C4 H5 F N6 O4'
_chemical_formula_weight         220.14

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           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   6.3720(6)
_cell_length_b                   9.3611(9)
_cell_length_c                   14.5803(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     869.70(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1917
_cell_measurement_theta_min      3.49
_cell_measurement_theta_max      24.7

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.160
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6598
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6304
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.489
_diffrn_reflns_theta_max         25.262
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1574
_reflns_number_gt                1268
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_max     1.000
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0117P)²+0.3806P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 443 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.0(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1574
_refine_ls_number_parameters     212
_refine_ls_number_restraints     343
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.0652
_refine_ls_wR_factor_gt          0.0599
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7309(7) 0.0601(4) 0.2901(3) 0.0390(10) Uani 1 1 d . . . . .
H1 H 0.7805 -0.0351 0.2839 0.047 Uiso 1 1 calc R U . . .
C2 C 0.8533(6) 0.1770(4) 0.3043(2) 0.0322(9) Uani 1 1 d . . . . .
H2 H 1.0017 0.1813 0.3097 0.039 Uiso 1 1 calc R U . . .
N1 N 0.7145(5) 0.2850(3) 0.30874(18) 0.0226(7) Uani 1 1 d . . . . .
N2 N 0.5161(5) 0.2401(3) 0.29744(19) 0.0278(7) Uani 1 1 d . . . . .
N3 N 0.5276(5) 0.1006(3) 0.28615(19) 0.0338(8) Uani 1 1 d . . . . .
N4 N 0.7628(5) 0.4296(3) 0.32187(19) 0.0233(7) Uani 1 1 d D . . . .
H4A H 0.708(5) 0.476(3) 0.2763(19) 0.028 Uiso 1 1 d D U . . .
C3 C 0.6814(5) 0.4828(3) 0.4094(2) 0.0215(7) Uani 0.47(5) 1 d D U P A 1
H3A H 0.6232 0.4034 0.4464 0.026 Uiso 0.47(5) 1 calc R U P A 1
H3B H 0.5696 0.5544 0.3990 0.026 Uiso 0.47(5) 1 calc R U P A 1
C4 C 0.863(2) 0.5485(19) 0.4566(12) 0.023(2) Uani 0.47(5) 1 d D U P A 1
F1 F 0.955(3) 0.656(2) 0.4117(16) 0.032(3) Uani 0.47(5) 1 d D U P A 1
N5 N 0.816(3) 0.607(2) 0.5536(11) 0.026(3) Uani 0.47(5) 1 d D U P A 1
O1 O 0.662(4) 0.561(4) 0.5917(18) 0.032(4) Uani 0.47(5) 1 d D U P A 1
O2 O 0.947(4) 0.689(3) 0.5835(18) 0.041(4) Uani 0.47(5) 1 d D U P A 1
N6 N 1.039(2) 0.435(2) 0.4765(13) 0.031(3) Uani 0.47(5) 1 d D U P A 1
O3 O 0.970(4) 0.322(2) 0.499(3) 0.038(4) Uani 0.47(5) 1 d D U P A 1
O4 O 1.215(2) 0.483(2) 0.4724(17) 0.066(4) Uani 0.47(5) 1 d D U P A 1
C3' C 0.6814(5) 0.4828(3) 0.4094(2) 0.0215(7) Uani 0.53(5) 1 d D U P A 2
H3'1 H 0.6300 0.4021 0.4471 0.026 Uiso 0.53(5) 1 calc R U P A 2
H3'2 H 0.5629 0.5489 0.3984 0.026 Uiso 0.53(5) 1 calc R U P A 2
C4' C 0.856(2) 0.5598(16) 0.4591(11) 0.023(2) Uani 0.53(5) 1 d D U P A 2
F1' F 0.911(3) 0.6805(18) 0.4150(14) 0.038(3) Uani 0.53(5) 1 d D U P A 2
N5' N 0.792(3) 0.601(2) 0.5562(10) 0.026(3) Uani 0.53(5) 1 d D U P A 2
O1' O 0.650(4) 0.533(3) 0.5910(16) 0.038(4) Uani 0.53(5) 1 d D U P A 2
O2' O 0.889(3) 0.700(2) 0.5901(15) 0.040(3) Uani 0.53(5) 1 d D U P A 2
N6' N 1.0493(19) 0.466(2) 0.4678(12) 0.033(3) Uani 0.53(5) 1 d D U P A 2
O3' O 1.020(4) 0.346(2) 0.496(2) 0.040(3) Uani 0.53(5) 1 d D U P A 2
O4' O 1.214(2) 0.512(3) 0.4430(18) 0.086(5) Uani 0.53(5) 1 d D U 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
C1 N3 1.351(5) . ?
C1 C2 1.359(5) . ?
C1 H1 0.9500 . ?
C2 N1 1.345(5) . ?
C2 H2 0.9500 . ?
N1 N2 1.342(4) . ?
N1 N4 1.401(4) . ?
N2 N3 1.318(4) . ?
N4 C3' 1.465(4) . ?
N4 C3 1.465(4) . ?
N4 H4A 0.87(2) . ?
C3 C4 1.480(16) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 F1 1.334(14) . ?
C4 N5 1.545(16) . ?
C4 N6 1.567(16) . ?
N5 O1 1.208(14) . ?
N5 O2 1.218(14) . ?
N6 O3 1.197(14) . ?
N6 O4 1.208(14) . ?
C3' C4' 1.513(14) . ?
C3' H3'1 0.9900 . ?
C3' H3'2 0.9900 . ?
C4' F1' 1.344(12) . ?
C4' N6' 1.514(14) . ?
C4' N5' 1.525(15) . ?
N5' O1' 1.216(13) . ?
N5' O2' 1.219(13) . ?
N6' O4' 1.193(12) . ?
N6' O3' 1.215(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 C1 C2 109.3(3) . . ?
N3 C1 H1 125.4 . . ?
C2 C1 H1 125.4 . . ?
N1 C2 C1 103.6(3) . . ?
N1 C2 H2 128.2 . . ?
C1 C2 H2 128.2 . . ?
N2 N1 C2 112.2(3) . . ?
N2 N1 N4 121.7(3) . . ?
C2 N1 N4 126.1(3) . . ?
N3 N2 N1 105.8(3) . . ?
N2 N3 C1 109.1(3) . . ?
N1 N4 C3' 111.7(3) . . ?
N1 N4 C3 111.7(3) . . ?
N1 N4 H4A 107(2) . . ?
C3' N4 H4A 111(2) . . ?
C3 N4 H4A 111(2) . . ?
N4 C3 C4 105.7(7) . . ?
N4 C3 H3A 110.6 . . ?
C4 C3 H3A 110.6 . . ?
N4 C3 H3B 110.6 . . ?
C4 C3 H3B 110.6 . . ?
H3A C3 H3B 108.7 . . ?
F1 C4 C3 115.4(14) . . ?
F1 C4 N5 105.6(12) . . ?
C3 C4 N5 114.9(10) . . ?
F1 C4 N6 106.5(11) . . ?
C3 C4 N6 111.3(10) . . ?
N5 C4 N6 101.9(12) . . ?
O1 N5 O2 128.2(17) . . ?
O1 N5 C4 117.0(14) . . ?
O2 N5 C4 114.8(13) . . ?
O3 N6 O4 132.7(16) . . ?
O3 N6 C4 113.1(13) . . ?
O4 N6 C4 114.0(12) . . ?
N4 C3' C4' 108.6(6) . . ?
N4 C3' H3'1 110.0 . . ?
C4' C3' H3'1 110.0 . . ?
N4 C3' H3'2 110.0 . . ?
C4' C3' H3'2 110.0 . . ?
H3'1 C3' H3'2 108.4 . . ?
F1' C4' N6' 108.5(10) . . ?
F1' C4' C3' 111.2(12) . . ?
N6' C4' C3' 111.3(9) . . ?
F1' C4' N5' 107.4(11) . . ?
N6' C4' N5' 106.7(10) . . ?
C3' C4' N5' 111.6(9) . . ?
O1' N5' O2' 127.3(15) . . ?
O1' N5' C4' 117.0(12) . . ?
O2' N5' C4' 115.7(12) . . ?
O4' N6' O3' 125.1(14) . . ?
O4' N6' C4' 118.8(11) . . ?
O3' N6' C4' 116.0(11) . . ?

_refine_diff_density_max         0.151
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.041

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

data_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1561908'
_audit_update_record             
;
2017-07-13 deposited with the CCDC.
2018-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H4 F N7 O6'
_chemical_formula_sum            'C4 H4 F N7 O6'
_chemical_formula_weight         265.14

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

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

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

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

_cell_length_a                   5.0674(7)
_cell_length_b                   22.537(3)
_cell_length_c                   8.3180(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.747(4)
_cell_angle_gamma                90
_cell_volume                     926.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    172(2)
_cell_measurement_reflns_used    1146
_cell_measurement_theta_min      3.09
_cell_measurement_theta_max      24.70

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.901
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.187
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5300
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      172(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5269
_diffrn_reflns_av_unetI/netI     0.0914
_diffrn_reflns_av_R_equivalents  0.0906
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.094
_diffrn_reflns_theta_max         25.443
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1693
_reflns_number_gt                1144
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0557P)²+2.8960P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1693
_refine_ls_number_parameters     194
_refine_ls_number_restraints     350
_refine_ls_R_factor_all          0.1278
_refine_ls_R_factor_gt           0.0812
_refine_ls_wR_factor_ref         0.1797
_refine_ls_wR_factor_gt          0.1619
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7517(9) 0.08309(19) 0.1286(5) 0.0102(10) Uani 1 1 d . . . . .
C2 C 0.5697(9) 0.0666(2) -0.1160(6) 0.0157(11) Uani 1 1 d . . . . .
H2 H 0.5364 0.0594 -0.2313 0.019 Uiso 1 1 calc R U . . .
N1 N 0.3798(8) 0.06989(17) -0.0286(5) 0.0128(9) Uani 1 1 d . U . . .
H1A H 0.211(11) 0.066(2) -0.054(6) 0.015 Uiso 1 1 d . U . . .
N2 N 0.4927(7) 0.08097(17) 0.1325(5) 0.0138(9) Uani 1 1 d . . . . .
N3 N 0.8116(7) 0.07468(18) -0.0193(5) 0.0144(9) Uani 1 1 d . . . . .
N4 N 0.9470(8) 0.09627(17) 0.2736(5) 0.0142(9) Uani 1 1 d . . . . .
N5 N 1.0970(8) 0.04931(19) 0.3548(5) 0.0154(9) Uani 1 1 d . . . . .
O1 O 1.2842(7) 0.06159(16) 0.4675(4) 0.0239(9) Uani 1 1 d . . . . .
O2 O 1.0230(7) -0.00068(15) 0.3073(4) 0.0219(8) Uani 1 1 d . . . . .
C3 C 1.0766(9) 0.1545(2) 0.2937(6) 0.0168(10) Uani 0.293(3) 1 d D U P A 1
H3A H 1.0472 0.1748 0.1857 0.020 Uiso 0.293(3) 1 calc R U P A 1
H3B H 1.2739 0.1497 0.3364 0.020 Uiso 0.293(3) 1 calc R U P A 1
C4 C 0.960(3) 0.1910(5) 0.4115(14) 0.015(4) Uiso 0.293(3) 1 d D U P A 1
F1 F 0.695(2) 0.1999(7) 0.362(2) 0.014(5) Uiso 0.293(3) 1 d D U P A 1
N6 N 1.086(3) 0.2531(5) 0.444(2) 0.027(6) Uiso 0.293(3) 1 d D U P A 1
O3 O 1.263(3) 0.2661(6) 0.375(3) 0.012(4) Uiso 0.293(3) 1 d D U P A 1
O4 O 0.996(4) 0.2828(7) 0.542(2) 0.029(5) Uiso 0.293(3) 1 d D U P A 1
N7 N 1.012(3) 0.1638(7) 0.5844(13) 0.017(4) Uiso 0.293(3) 1 d D U P A 1
O5 O 1.235(3) 0.1747(7) 0.6712(16) 0.020(3) Uiso 0.293(3) 1 d D U P A 1
O6 O 0.838(4) 0.1319(6) 0.6160(18) 0.020(3) Uiso 0.293(3) 1 d D U P A 1
C3' C 1.0766(9) 0.1545(2) 0.2937(6) 0.0168(10) Uani 0.411(3) 1 d D U P A 2
H3'1 H 1.0421 0.1753 0.1863 0.020 Uiso 0.411(3) 1 calc R U P A 2
H3'2 H 1.2746 0.1496 0.3327 0.020 Uiso 0.411(3) 1 calc R U P A 2
C4' C 0.966(2) 0.1910(4) 0.4175(11) 0.014(4) Uiso 0.411(3) 1 d D U P A 2
F1' F 0.7012(14) 0.1889(4) 0.4002(11) 0.020(3) Uiso 0.411(3) 1 d D U P A 2
N6' N 1.061(2) 0.2555(4) 0.4161(14) 0.019(4) Uiso 0.411(3) 1 d D U P A 2
O3' O 1.216(2) 0.2666(5) 0.3259(15) 0.042(4) Uiso 0.411(3) 1 d D U P A 2
O4' O 0.976(3) 0.2911(5) 0.5016(19) 0.025(4) Uiso 0.411(3) 1 d D U P A 2
N7' N 1.093(2) 0.1701(5) 0.5936(11) 0.022(3) Uiso 0.411(3) 1 d D U P A 2
O5' O 1.3253(19) 0.1850(4) 0.6457(11) 0.027(3) Uiso 0.411(3) 1 d D U P A 2
O6' O 0.954(3) 0.1372(5) 0.6571(13) 0.036(3) Uiso 0.411(3) 1 d D U P A 2
C3A C 1.0766(9) 0.1545(2) 0.2937(6) 0.0168(10) Uani 0.295(3) 1 d D U P A 3
H3A1 H 1.0550 0.1742 0.1853 0.020 Uiso 0.295(3) 1 calc R U P A 3
H3A2 H 1.2724 0.1501 0.3422 0.020 Uiso 0.295(3) 1 calc R U P A 3
C4A C 0.946(3) 0.1908(5) 0.4049(14) 0.016(4) Uiso 0.295(3) 1 d D U P A 3
F1A F 0.6879(19) 0.2017(6) 0.3254(16) 0.019(4) Uiso 0.295(3) 1 d D U P A 3
N6A N 1.061(3) 0.2526(5) 0.4514(18) 0.020(5) Uiso 0.295(3) 1 d D U P A 3
O3A O 1.283(3) 0.2633(6) 0.426(2) 0.028(5) Uiso 0.295(3) 1 d D U P A 3
O4A O 0.906(3) 0.2860(6) 0.506(2) 0.015(4) Uiso 0.295(3) 1 d D U P A 3
N7A N 0.940(3) 0.1618(7) 0.5691(13) 0.024(4) Uiso 0.295(3) 1 d D U P A 3
O5A O 1.150(3) 0.1631(7) 0.6760(17) 0.034(4) Uiso 0.295(3) 1 d D U P A 3
O6A O 0.728(3) 0.1397(7) 0.5817(17) 0.033(4) Uiso 0.295(3) 1 d D U P A 3


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.321(6) . ?
C1 N3 1.344(6) . ?
C1 N4 1.412(6) . ?
C2 N3 1.322(6) . ?
C2 N1 1.330(6) . ?
C2 H2 0.9500 . ?
N1 N2 1.359(5) . ?
N1 H1A 0.84(5) . ?
N4 N5 1.388(6) . ?
N4 C3A 1.460(6) . ?
N4 C3 1.460(6) . ?
N4 C3' 1.460(6) . ?
N5 O1 1.210(5) . ?
N5 O2 1.225(5) . ?
C3 C4 1.497(12) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 F1 1.330(12) . ?
C4 N7 1.531(11) . ?
C4 N6 1.537(11) . ?
N6 O3 1.203(12) . ?
N6 O4 1.221(12) . ?
N7 O6 1.214(18) . ?
N7 O5 1.223(14) . ?
C3' C4' 1.518(11) . ?
C3' H3'1 0.9900 . ?
C3' H3'2 0.9900 . ?
C4' F1' 1.319(10) . ?
C4' N6' 1.530(10) . ?
C4' N7' 1.538(10) . ?
N6' O4' 1.212(10) . ?
N6' O3' 1.228(10) . ?
N7' O5' 1.210(12) . ?
N7' O6' 1.218(14) . ?
C3A C4A 1.494(12) . ?
C3A H3A1 0.9900 . ?
C3A H3A2 0.9900 . ?
C4A F1A 1.353(12) . ?
C4A N7A 1.521(12) . ?
C4A N6A 1.525(11) . ?
N6A O3A 1.214(12) . ?
N6A O4A 1.242(11) . ?
N7A O6A 1.212(17) . ?
N7A O5A 1.227(13) . ?

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 C1 N3 116.3(4) . . ?
N2 C1 N4 120.0(4) . . ?
N3 C1 N4 123.7(4) . . ?
N3 C2 N1 110.2(4) . . ?
N3 C2 H2 124.9 . . ?
N1 C2 H2 124.9 . . ?
C2 N1 N2 110.6(4) . . ?
C2 N1 H1A 133(3) . . ?
N2 N1 H1A 117(3) . . ?
C1 N2 N1 100.8(4) . . ?
C2 N3 C1 102.2(4) . . ?
N5 N4 C1 117.4(4) . . ?
N5 N4 C3A 116.4(4) . . ?
C1 N4 C3A 120.0(4) . . ?
N5 N4 C3 116.4(4) . . ?
C1 N4 C3 120.0(4) . . ?
N5 N4 C3' 116.4(4) . . ?
C1 N4 C3' 120.0(4) . . ?
O1 N5 O2 126.3(4) . . ?
O1 N5 N4 117.0(4) . . ?
O2 N5 N4 116.7(4) . . ?
N4 C3 C4 109.7(6) . . ?
N4 C3 H3A 109.7 . . ?
C4 C3 H3A 109.7 . . ?
N4 C3 H3B 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
F1 C4 C3 113.3(10) . . ?
F1 C4 N7 107.9(10) . . ?
C3 C4 N7 112.5(9) . . ?
F1 C4 N6 105.5(9) . . ?
C3 C4 N6 114.0(8) . . ?
N7 C4 N6 102.8(9) . . ?
O3 N6 O4 127.9(13) . . ?
O3 N6 C4 117.5(10) . . ?
O4 N6 C4 114.5(11) . . ?
O6 N7 O5 127.9(13) . . ?
O6 N7 C4 117.1(12) . . ?
O5 N7 C4 114.9(12) . . ?
N4 C3' C4' 110.0(5) . . ?
N4 C3' H3'1 109.7 . . ?
C4' C3' H3'1 109.7 . . ?
N4 C3' H3'2 109.7 . . ?
C4' C3' H3'2 109.7 . . ?
H3'1 C3' H3'2 108.2 . . ?
F1' C4' C3' 115.2(7) . . ?
F1' C4' N6' 110.2(8) . . ?
C3' C4' N6' 110.3(7) . . ?
F1' C4' N7' 107.1(8) . . ?
C3' C4' N7' 109.9(7) . . ?
N6' C4' N7' 103.4(7) . . ?
O4' N6' O3' 125.5(10) . . ?
O4' N6' C4' 118.2(9) . . ?
O3' N6' C4' 116.3(8) . . ?
O5' N7' O6' 128.4(10) . . ?
O5' N7' C4' 115.2(9) . . ?
O6' N7' C4' 116.2(10) . . ?
N4 C3A C4A 108.4(5) . . ?
N4 C3A H3A1 110.0 . . ?
C4A C3A H3A1 110.0 . . ?
N4 C3A H3A2 110.0 . . ?
C4A C3A H3A2 110.0 . . ?
H3A1 C3A H3A2 108.4 . . ?
F1A C4A C3A 108.0(9) . . ?
F1A C4A N7A 107.9(9) . . ?
C3A C4A N7A 114.8(9) . . ?
F1A C4A N6A 103.4(9) . . ?
C3A C4A N6A 117.5(8) . . ?
N7A C4A N6A 104.3(9) . . ?
O3A N6A O4A 128.9(12) . . ?
O3A N6A C4A 116.9(10) . . ?
O4A N6A C4A 114.2(10) . . ?
O6A N7A O5A 126.3(12) . . ?
O6A N7A C4A 116.7(11) . . ?
O5A N7A C4A 117.1(12) . . ?

_refine_diff_density_max         0.315
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.084

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

data_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1540476'
_audit_update_record             
;
2017-03-27 deposited with the CCDC.
2018-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H5 F N6 O4'
_chemical_formula_sum            'C4 H5 F N6 O4'
_chemical_formula_weight         220.14

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

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

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

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

_cell_length_a                   9.4897(15)
_cell_length_b                   7.5220(11)
_cell_length_c                   11.9071(18)
_cell_angle_alpha                90
_cell_angle_beta                 105.455(5)
_cell_angle_gamma                90
_cell_volume                     819.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    770
_cell_measurement_theta_min      3.20
_cell_measurement_theta_max      24.17

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.785
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.170
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6230
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4112
_diffrn_reflns_av_unetI/netI     0.0827
_diffrn_reflns_av_R_equivalents  0.0840
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.197
_diffrn_reflns_theta_max         25.352
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1491
_reflns_number_gt                927
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0373P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1491
_refine_ls_number_parameters     139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1046
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.0963
_refine_ls_wR_factor_gt          0.0821
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3516(3) 0.0340(4) 0.3307(2) 0.0172(7) Uani 1 1 d . . . . .
H1 H 0.3889 0.1194 0.2874 0.021 Uiso 1 1 calc R U . . .
C2 C 0.2403(3) -0.0857(4) 0.4475(2) 0.0189(7) Uani 1 1 d . . . . .
H2 H 0.1840 -0.1009 0.5019 0.023 Uiso 1 1 calc R U . . .
C3 C 0.3251(3) 0.3532(4) 0.5022(2) 0.0146(7) Uani 1 1 d . . . . .
H3A H 0.3146 0.4766 0.4722 0.017 Uiso 1 1 calc R U . . .
H3B H 0.4243 0.3103 0.5038 0.017 Uiso 1 1 calc R U . . .
C4 C 0.3033(3) 0.3475(4) 0.6224(2) 0.0136(7) Uani 1 1 d . . . . .
F1 F 0.30514(19) 0.1829(2) 0.66503(13) 0.0202(4) Uani 1 1 d . . . . .
N1 N 0.2995(3) -0.2144(3) 0.4035(2) 0.0221(7) Uani 1 1 d . . . . .
N2 N 0.3716(3) -0.1364(3) 0.3271(2) 0.0202(6) Uani 1 1 d . . . . .
N3 N 0.2696(3) 0.0729(3) 0.40526(19) 0.0137(6) Uani 1 1 d . . . . .
N4 N 0.2151(3) 0.2394(3) 0.4278(2) 0.0159(6) Uani 1 1 d . . . . .
H4A H 0.180(3) 0.284(4) 0.362(3) 0.019 Uiso 1 1 d . U . . .
N5 N 0.4174(3) 0.4545(3) 0.7119(2) 0.0166(6) Uani 1 1 d . . . . .
N6 N 0.1571(3) 0.4309(4) 0.6262(2) 0.0198(6) Uani 1 1 d . . . . .
O1 O 0.4211(2) 0.4303(3) 0.81346(16) 0.0247(6) Uani 1 1 d . . . . .
O2 O 0.4951(3) 0.5541(3) 0.67393(18) 0.0273(6) Uani 1 1 d . . . . .
O3 O 0.0767(3) 0.3456(3) 0.6690(2) 0.0371(6) Uani 1 1 d . . . . .
O4 O 0.1353(2) 0.5792(3) 0.58460(18) 0.0274(6) 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
C1 N2 1.298(4) . ?
C1 N3 1.359(3) . ?
C1 H1 0.9500 . ?
C2 N1 1.297(4) . ?
C2 N3 1.352(4) . ?
C2 H2 0.9500 . ?
C3 N4 1.455(4) . ?
C3 C4 1.501(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 F1 1.337(3) . ?
C4 N5 1.530(4) . ?
C4 N6 1.534(4) . ?
N1 N2 1.404(3) . ?
N3 N4 1.408(3) . ?
N4 H4A 0.83(3) . ?
N5 O1 1.214(3) . ?
N5 O2 1.219(3) . ?
N6 O3 1.209(3) . ?
N6 O4 1.216(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N3 110.4(3) . . ?
N2 C1 H1 124.8 . . ?
N3 C1 H1 124.8 . . ?
N1 C2 N3 110.7(3) . . ?
N1 C2 H2 124.6 . . ?
N3 C2 H2 124.6 . . ?
N4 C3 C4 107.7(2) . . ?
N4 C3 H3A 110.2 . . ?
C4 C3 H3A 110.2 . . ?
N4 C3 H3B 110.2 . . ?
C4 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
F1 C4 C3 113.4(2) . . ?
F1 C4 N5 106.7(2) . . ?
C3 C4 N5 113.4(2) . . ?
F1 C4 N6 106.8(2) . . ?
C3 C4 N6 111.9(2) . . ?
N5 C4 N6 104.0(2) . . ?
C2 N1 N2 106.7(2) . . ?
C1 N2 N1 106.8(2) . . ?
C2 N3 C1 105.2(2) . . ?
C2 N3 N4 126.3(2) . . ?
C1 N3 N4 128.3(2) . . ?
N3 N4 C3 113.5(2) . . ?
N3 N4 H4A 105(2) . . ?
C3 N4 H4A 112(2) . . ?
O1 N5 O2 127.0(3) . . ?
O1 N5 C4 116.2(2) . . ?
O2 N5 C4 116.8(2) . . ?
O3 N6 O4 126.9(3) . . ?
O3 N6 C4 118.2(3) . . ?
O4 N6 C4 114.9(2) . . ?

_refine_diff_density_max         0.279
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.066

