# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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 
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data_mo_2017247-szho1_0ma
_database_code_depnum_ccdc_archive 'CCDC 1588934'
_audit_update_record             
;
2017-12-04 deposited with the CCDC.
2018-04-23 downloaded from the CCDC.
;
_audit_creation_date             2017-04-26
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H12 F N5 O4'
_chemical_formula_sum            'C10 H12 F N5 O4'
_chemical_formula_weight         285.25
_chemical_absolute_configuration unk
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   7.8851(12)
_cell_length_b                   11.2622(16)
_cell_length_c                   13.1273(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1165.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1385
_cell_measurement_temperature    205
_cell_measurement_theta_max      21.64
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6599
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0715 before and 0.0604 after correction.
The Ratio of minimum to maximum transmission is 0.8851.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_av_unetI/netI     0.0658
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8939
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         2.383
_diffrn_ambient_temperature      205.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_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_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2176
_reflns_number_total             2672
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.256
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   1.7(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2672
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.008
_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)+(0.0515P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1093
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: -0.7(15)
 1.7(15)
2. 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 O(H) groups
3.a Rotating group:
 N2(H2A,H2B)
3.b Ternary CH refined with riding coordinates:
 C3'(H3'), C4'(H4'), C2'(H2'), C1'(H1')
3.c Secondary CH2 refined with riding coordinates:
 C5'(H5'A,H5'B)
3.d Aromatic/amide H refined with riding coordinates:
 N1(H1), C8(H8)
3.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), 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
F1 F 0.2571(3) 0.19146(17) 0.12845(14) 0.0291(5) Uani 1 1 d . . . . .
O3 O 0.3888(3) 0.3640(2) 0.00808(14) 0.0209(5) Uani 1 1 d . . . . .
H3 H 0.2992 0.4011 -0.0014 0.031 Uiso 1 1 calc GR . . . .
O2 O 0.9033(3) 0.3147(2) 0.13929(16) 0.0223(5) Uani 1 1 d . . . . .
H2 H 0.9217 0.2677 0.0919 0.033 Uiso 1 1 calc GR . . . .
O1 O 0.3830(3) 0.4489(2) 0.69402(15) 0.0263(6) Uani 1 1 d . . . . .
O4' O 0.5873(3) 0.2594(2) 0.23442(16) 0.0288(6) Uani 1 1 d . . . . .
N7 N 0.3712(4) 0.4887(2) 0.46067(19) 0.0220(6) Uani 1 1 d . . . . .
N1 N 0.4269(3) 0.2551(2) 0.65334(18) 0.0195(6) Uani 1 1 d . . . . .
H1 H 0.4364 0.2388 0.7179 0.023 Uiso 1 1 calc R . . . .
N3 N 0.4368(3) 0.1739(2) 0.48571(18) 0.0203(6) Uani 1 1 d . . . . .
N9 N 0.3997(4) 0.3294(2) 0.35954(17) 0.0195(6) Uani 1 1 d . . . . .
N2 N 0.4496(4) 0.0524(3) 0.6269(2) 0.0259(7) Uani 1 1 d . . . . .
H2A H 0.5051 0.0552 0.6835 0.031 Uiso 1 1 d GR . . . .
H2B H 0.5028 0.0069 0.5849 0.031 Uiso 1 1 d GR . . . .
C4 C 0.4145(4) 0.2890(3) 0.4585(2) 0.0176(7) Uani 1 1 d . . . . .
C2 C 0.4389(4) 0.1616(3) 0.5865(2) 0.0176(7) Uani 1 1 d . . . . .
C5 C 0.3980(4) 0.3877(3) 0.5196(2) 0.0197(7) Uani 1 1 d . . . . .
C8 C 0.3744(4) 0.4504(3) 0.3664(2) 0.0224(7) Uani 1 1 d . . . . .
H8 H 0.3609 0.5002 0.3094 0.027 Uiso 1 1 calc R . . . .
C3' C 0.4282(4) 0.3642(3) 0.1131(2) 0.0173(7) Uani 1 1 d . . . . .
H3' H 0.4363 0.4470 0.1378 0.021 Uiso 1 1 calc R . . . .
C4' C 0.5964(4) 0.3010(3) 0.1306(2) 0.0179(6) Uani 1 1 d . . . . .
H4' H 0.6056 0.2323 0.0839 0.021 Uiso 1 1 calc R . . . .
C6 C 0.4008(4) 0.3732(3) 0.6273(2) 0.0193(6) Uani 1 1 d . . . . .
C5' C 0.7508(4) 0.3791(3) 0.1193(3) 0.0219(7) Uani 1 1 d . . . . .
H5'A H 0.7547 0.4112 0.0499 0.026 Uiso 1 1 calc R . . . .
H5'B H 0.7423 0.4461 0.1667 0.026 Uiso 1 1 calc R . . . .
C2' C 0.3064(4) 0.2950(3) 0.1799(2) 0.0193(7) Uani 1 1 d . . . . .
H2' H 0.2081 0.3434 0.2018 0.023 Uiso 1 1 calc R . . . .
C1' C 0.4162(4) 0.2557(3) 0.2692(2) 0.0194(7) Uani 1 1 d . . . . .
H1' H 0.3870 0.1727 0.2871 0.023 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0373(11) 0.0268(12) 0.0232(10) -0.0050(9) -0.0034(9) -0.0096(9)
O3 0.0232(11) 0.0272(14) 0.0124(10) 0.0016(9) -0.0041(9) 0.0058(10)
O2 0.0190(10) 0.0300(14) 0.0178(11) -0.0047(10) -0.0023(10) 0.0013(10)
O1 0.0403(14) 0.0220(14) 0.0166(11) -0.0063(10) 0.0002(11) 0.0001(11)
O4' 0.0215(11) 0.0500(16) 0.0149(10) 0.0099(11) 0.0026(10) 0.0124(12)
N7 0.0319(15) 0.0173(15) 0.0167(12) 0.0016(12) 0.0016(12) 0.0040(12)
N1 0.0286(14) 0.0202(16) 0.0097(11) -0.0008(10) -0.0001(10) 0.0025(12)
N3 0.0285(14) 0.0184(16) 0.0139(13) 0.0004(11) -0.0002(11) 0.0039(12)
N9 0.0285(14) 0.0190(15) 0.0111(12) -0.0008(11) 0.0002(12) 0.0041(12)
N2 0.0426(18) 0.0205(16) 0.0147(12) 0.0002(13) -0.0014(13) 0.0056(13)
C4 0.0197(15) 0.0205(18) 0.0126(13) 0.0008(13) 0.0005(13) 0.0028(13)
C2 0.0200(15) 0.0183(19) 0.0146(14) 0.0009(13) -0.0002(12) 0.0012(13)
C5 0.0245(15) 0.0180(17) 0.0165(14) 0.0010(12) 0.0007(14) 0.0043(14)
C8 0.0312(18) 0.0167(18) 0.0194(15) 0.0023(14) 0.0013(15) 0.0052(14)
C3' 0.0222(15) 0.0159(17) 0.0139(14) -0.0034(12) -0.0034(12) 0.0022(13)
C4' 0.0240(15) 0.0179(17) 0.0118(13) -0.0007(13) 0.0016(13) 0.0046(13)
C6 0.0193(14) 0.0209(17) 0.0176(14) -0.0020(14) 0.0009(14) -0.0005(14)
C5' 0.0210(15) 0.0216(19) 0.0230(16) -0.0007(15) -0.0037(14) 0.0011(14)
C2' 0.0221(15) 0.021(2) 0.0147(15) -0.0044(14) -0.0010(13) 0.0013(13)
C1' 0.0232(15) 0.0170(17) 0.0179(14) -0.0005(13) 0.0027(13) 0.0035(14)

_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 C2' 1.402(4) . ?
O3 H3 0.8300 . ?
O3 C3' 1.413(3) . ?
O2 H2 0.8300 . ?
O2 C5' 1.429(4) . ?
O1 C6 1.229(4) . ?
O4' C4' 1.443(3) . ?
O4' C1' 1.425(3) . ?
N7 C5 1.392(4) . ?
N7 C8 1.311(4) . ?
N1 H1 0.8700 . ?
N1 C2 1.374(4) . ?
N1 C6 1.389(4) . ?
N3 C4 1.355(4) . ?
N3 C2 1.330(4) . ?
N9 C4 1.382(4) . ?
N9 C8 1.381(4) . ?
N9 C1' 1.453(4) . ?
N2 H2A 0.8627 . ?
N2 H2B 0.8623 . ?
N2 C2 1.342(4) . ?
C4 C5 1.377(4) . ?
C5 C6 1.424(4) . ?
C8 H8 0.9400 . ?
C3' H3' 0.9900 . ?
C3' C4' 1.523(4) . ?
C3' C2' 1.516(4) . ?
C4' H4' 0.9900 . ?
C4' C5' 1.509(5) . ?
C5' H5'A 0.9800 . ?
C5' H5'B 0.9800 . ?
C2' H2' 0.9900 . ?
C2' C1' 1.524(4) . ?
C1' H1' 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' O3 H3 109.5 . . ?
C5' O2 H2 109.5 . . ?
C1' O4' C4' 111.1(2) . . ?
C8 N7 C5 104.7(3) . . ?
C2 N1 H1 117.0 . . ?
C2 N1 C6 126.0(3) . . ?
C6 N1 H1 117.0 . . ?
C2 N3 C4 111.3(3) . . ?
C4 N9 C1' 124.8(3) . . ?
C8 N9 C4 106.0(2) . . ?
C8 N9 C1' 129.1(3) . . ?
H2A N2 H2B 109.1 . . ?
C2 N2 H2A 109.8 . . ?
C2 N2 H2B 108.8 . . ?
N3 C4 N9 125.0(3) . . ?
N3 C4 C5 129.1(3) . . ?
C5 C4 N9 105.9(3) . . ?
N3 C2 N1 123.7(3) . . ?
N3 C2 N2 119.3(3) . . ?
N2 C2 N1 117.0(3) . . ?
N7 C5 C6 130.4(3) . . ?
C4 C5 N7 110.5(3) . . ?
C4 C5 C6 119.0(3) . . ?
N7 C8 N9 112.9(3) . . ?
N7 C8 H8 123.6 . . ?
N9 C8 H8 123.6 . . ?
O3 C3' H3' 109.6 . . ?
O3 C3' C4' 109.8(2) . . ?
O3 C3' C2' 115.1(3) . . ?
C4' C3' H3' 109.6 . . ?
C2' C3' H3' 109.6 . . ?
C2' C3' C4' 103.0(3) . . ?
O4' C4' C3' 104.5(2) . . ?
O4' C4' H4' 109.6 . . ?
O4' C4' C5' 108.8(3) . . ?
C3' C4' H4' 109.6 . . ?
C5' C4' C3' 114.5(3) . . ?
C5' C4' H4' 109.6 . . ?
O1 C6 N1 120.4(3) . . ?
O1 C6 C5 128.8(3) . . ?
N1 C6 C5 110.8(3) . . ?
O2 C5' C4' 111.4(3) . . ?
O2 C5' H5'A 109.3 . . ?
O2 C5' H5'B 109.3 . . ?
C4' C5' H5'A 109.3 . . ?
C4' C5' H5'B 109.3 . . ?
H5'A C5' H5'B 108.0 . . ?
F1 C2' C3' 108.9(2) . . ?
F1 C2' H2' 112.4 . . ?
F1 C2' C1' 106.6(3) . . ?
C3' C2' H2' 112.4 . . ?
C3' C2' C1' 103.6(3) . . ?
C1' C2' H2' 112.4 . . ?
O4' C1' N9 109.3(3) . . ?
O4' C1' C2' 106.4(2) . . ?
O4' C1' H1' 108.9 . . ?
N9 C1' C2' 114.3(3) . . ?
N9 C1' H1' 108.9 . . ?
C2' C1' H1' 108.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 -0.7(15)
2 1.7(15)
