# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2026

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
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data_241020lu_lgpz085522_0m
_database_code_depnum_ccdc_archive 'CCDC 2393345'
loop_
_audit_author_name
_audit_author_address
'Yujie Yan'
;SWUST
China
;
_audit_update_record             
;
2024-10-24 deposited with the CCDC.	2025-12-17 downloaded from the CCDC.
;
_audit_creation_date             2024-10-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H6 F N3 O4'
_chemical_formula_sum            'C7 H6 F N3 O4'
_chemical_formula_weight         215.15
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
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                   3.6529(2)
_cell_length_b                   31.8096(12)
_cell_length_c                   14.7708(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.369(2)
_cell_angle_gamma                90
_cell_volume                     1714.86(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3779
_cell_measurement_temperature    198.00
_cell_measurement_theta_max      27.37
_cell_measurement_theta_min      2.56
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6721
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1086 before and 0.0476 after correction.
The Ratio of minimum to maximum transmission is 0.9014.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7967
_diffrn_reflns_point_group_measured_fraction_full 0.778
_diffrn_reflns_point_group_measured_fraction_max 0.757
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.554
_diffrn_reflns_theta_min         1.882
_diffrn_ambient_temperature      198.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE TXS PHOTON II'
_diffrn_measurement_method       'ω and φ shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   TXS
_diffrn_source_current           40.0
_diffrn_source_power             1.8
_diffrn_source_type              'Rotaing Anode'
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.516
_reflns_Friedel_fraction_full    0.561
_reflns_Friedel_fraction_max     0.518
_reflns_number_gt                2725
_reflns_number_total             2992
_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 V8.40B (Bruker, 2019)'
_computing_data_collection       'APEX5 V2023.9-2 (Bruker, 2023)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 854 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         2992
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0350
_refine_ls_restrained_S_all      1.059
_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)+(0.0377P)²+1.3911P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0832
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C5(H5)
2.c X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C1(H1A,H1B,H1C)
;
_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
F2 F 0.5238(6) 0.51589(6) 0.33015(14) 0.0345(5) Uani 1 1 d . . . . .
F1 F -0.0590(7) 0.21501(6) 0.48522(17) 0.0386(6) Uani 1 1 d . . . . .
O5 O 0.9321(9) 0.58311(8) 0.28280(18) 0.0391(7) Uani 1 1 d . . . . .
O6 O 0.6378(9) 0.63200(8) 0.3509(2) 0.0404(7) Uani 1 1 d . . . . .
O7 O 0.7430(8) 0.60411(8) 0.69720(19) 0.0373(7) Uani 1 1 d . . . . .
O8 O 1.0560(9) 0.54838(8) 0.73078(19) 0.0418(7) Uani 1 1 d . . . . .
O4 O 0.4078(9) 0.39512(8) 0.60309(19) 0.0387(7) Uani 1 1 d . . . . .
O3 O 0.0863(8) 0.40834(7) 0.4807(2) 0.0381(7) Uani 1 1 d . . . . .
O2 O 0.0140(9) 0.27571(10) 0.26969(18) 0.0440(7) Uani 1 1 d . . . . .
N5 N 0.8789(9) 0.57040(9) 0.6764(2) 0.0270(6) Uani 1 1 d . . . . .
O1 O 0.3357(10) 0.22673(9) 0.3367(2) 0.0470(8) Uani 1 1 d . . . . .
N4 N 0.7717(9) 0.59695(9) 0.3481(2) 0.0271(6) Uani 1 1 d . . . . .
N2 N 0.2242(9) 0.38380(8) 0.5360(2) 0.0255(6) Uani 1 1 d . . . . .
N1 N 0.1588(9) 0.25952(9) 0.3376(2) 0.0301(7) Uani 1 1 d . . . . .
N6 N 0.7281(10) 0.48399(9) 0.6377(2) 0.0346(7) Uani 1 1 d . . . . .
H6A H 0.671047 0.496339 0.688612 0.042 Uiso 1 1 d R U . . .
H6B H 0.566503 0.464179 0.624242 0.042 Uiso 1 1 d R U . . .
N3 N 0.0542(10) 0.32983(10) 0.6826(2) 0.0354(8) Uani 1 1 d . . . . .
H3A H -0.010603 0.313298 0.726907 0.043 Uiso 1 1 calc R U . . .
H3B H 0.104465 0.356455 0.693415 0.043 Uiso 1 1 calc R U . . .
C11 C 0.7244(9) 0.51267(10) 0.5712(2) 0.0228(7) Uani 1 1 d . . . . .
C10 C 0.8182(9) 0.55557(9) 0.5843(2) 0.0208(7) Uani 1 1 d . . . . .
C4 C 0.0762(9) 0.31453(10) 0.5989(2) 0.0217(7) Uani 1 1 d . . . . .
C13 C 0.6308(10) 0.52823(10) 0.4135(2) 0.0236(7) Uani 1 1 d . . . . .
C12 C 0.6169(10) 0.50029(10) 0.4822(3) 0.0248(7) Uani 1 1 d . . . . .
H12 H 0.534845 0.472390 0.470659 0.030 Uiso 1 1 calc R U . . .
C9 C 0.8392(9) 0.58462(10) 0.5134(2) 0.0205(6) Uani 1 1 d . . . . .
C2 C 0.1963(8) 0.32274(10) 0.4346(2) 0.0191(6) Uani 1 1 d . . . . .
C3 C 0.1655(9) 0.33896(9) 0.5223(2) 0.0199(7) Uani 1 1 d . . . . .
C5 C -0.0051(10) 0.27184(10) 0.5825(2) 0.0239(7) Uani 1 1 d . . . . .
H5 H -0.078259 0.254364 0.630660 0.029 Uiso 1 1 calc R U . . .
C7 C 0.1231(9) 0.28005(10) 0.4249(2) 0.0226(7) Uani 1 1 d . . . . .
C6 C 0.0209(10) 0.25567(9) 0.4983(2) 0.0239(7) Uani 1 1 d . . . . .
C8 C 0.9874(10) 0.62861(9) 0.5288(3) 0.0261(7) Uani 1 1 d . . . . .
H8A H 0.784855 0.647771 0.540616 0.039 Uiso 1 1 calc R U . . .
H8B H 1.111142 0.637994 0.474705 0.039 Uiso 1 1 calc R U . . .
H8C H 1.162311 0.628550 0.580892 0.039 Uiso 1 1 calc R U . . .
C14 C 0.7473(9) 0.56996(9) 0.4269(2) 0.0218(7) Uani 1 1 d . . . . .
C1 C 0.3335(10) 0.34884(11) 0.3580(2) 0.0251(7) Uani 1 1 d . . . . .
H1A H 0.124999 0.361523 0.324234 0.038 Uiso 1 1 calc R U . . .
H1B H 0.470347 0.330902 0.317364 0.038 Uiso 1 1 calc R U . . .
H1C H 0.494619 0.371080 0.382543 0.038 Uiso 1 1 calc R U . . .


_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
F2 C13 1.335(4) . ?
F1 C6 1.338(3) . ?
O5 N4 1.231(4) . ?
O6 N4 1.219(4) . ?
O7 N5 1.226(4) . ?
O8 N5 1.229(4) . ?
O4 N2 1.228(4) . ?
O3 N2 1.223(4) . ?
O2 N1 1.227(4) . ?
N5 C10 1.448(4) . ?
O1 N1 1.227(4) . ?
N4 C14 1.452(4) . ?
N2 C3 1.455(4) . ?
N1 C7 1.457(4) . ?
N6 H6A 0.8805 . ?
N6 H6B 0.8806 . ?
N6 C11 1.341(4) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N3 C4 1.333(4) . ?
C11 C10 1.419(4) . ?
C11 C12 1.412(5) . ?
C10 C9 1.401(4) . ?
C4 C3 1.422(4) . ?
C4 C5 1.409(4) . ?
C13 C12 1.351(5) . ?
C13 C14 1.405(4) . ?
C12 H12 0.9500 . ?
C9 C8 1.514(4) . ?
C9 C14 1.388(5) . ?
C2 C3 1.403(4) . ?
C2 C7 1.390(5) . ?
C2 C1 1.506(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.353(5) . ?
C7 C6 1.396(5) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?

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
O7 N5 O8 122.8(3) . . ?
O7 N5 C10 118.2(3) . . ?
O8 N5 C10 119.0(3) . . ?
O5 N4 C14 117.6(3) . . ?
O6 N4 O5 123.9(3) . . ?
O6 N4 C14 118.4(3) . . ?
O4 N2 C3 118.2(3) . . ?
O3 N2 O4 123.2(3) . . ?
O3 N2 C3 118.6(3) . . ?
O2 N1 O1 123.9(3) . . ?
O2 N1 C7 119.0(3) . . ?
O1 N1 C7 117.2(3) . . ?
H6A N6 H6B 109.4 . . ?
C11 N6 H6A 109.1 . . ?
C11 N6 H6B 109.5 . . ?
H3A N3 H3B 120.0 . . ?
C4 N3 H3A 120.0 . . ?
C4 N3 H3B 120.0 . . ?
N6 C11 C10 124.0(3) . . ?
N6 C11 C12 119.1(3) . . ?
C12 C11 C10 116.9(3) . . ?
C11 C10 N5 117.9(3) . . ?
C9 C10 N5 118.5(3) . . ?
C9 C10 C11 123.5(3) . . ?
N3 C4 C3 124.2(3) . . ?
N3 C4 C5 119.4(3) . . ?
C5 C4 C3 116.3(3) . . ?
F2 C13 C12 118.7(3) . . ?
F2 C13 C14 118.9(3) . . ?
C12 C13 C14 122.4(3) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.9(3) . . ?
C13 C12 H12 120.1 . . ?
C10 C9 C8 121.8(3) . . ?
C14 C9 C10 116.6(3) . . ?
C14 C9 C8 121.3(3) . . ?
C3 C2 C1 122.2(3) . . ?
C7 C2 C3 115.6(3) . . ?
C7 C2 C1 122.0(3) . . ?
C4 C3 N2 117.6(3) . . ?
C2 C3 N2 118.1(3) . . ?
C2 C3 C4 124.3(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C2 C7 N1 120.3(3) . . ?
C2 C7 C6 121.3(3) . . ?
C6 C7 N1 118.4(3) . . ?
F1 C6 C5 118.5(3) . . ?
F1 C6 C7 119.3(3) . . ?
C5 C6 C7 122.2(3) . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C13 C14 N4 118.3(3) . . ?
C9 C14 N4 121.2(3) . . ?
C9 C14 C13 120.5(3) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F2 C13 C12 C11 -179.3(3) . . . . ?
F2 C13 C14 N4 -4.5(5) . . . . ?
F2 C13 C14 C9 176.1(3) . . . . ?
O5 N4 C14 C13 -48.5(5) . . . . ?
O5 N4 C14 C9 130.9(4) . . . . ?
O6 N4 C14 C13 132.5(4) . . . . ?
O6 N4 C14 C9 -48.0(5) . . . . ?
O7 N5 C10 C11 -135.6(3) . . . . ?
O7 N5 C10 C9 41.6(5) . . . . ?
O8 N5 C10 C11 42.7(5) . . . . ?
O8 N5 C10 C9 -140.1(3) . . . . ?
O4 N2 C3 C4 43.7(4) . . . . ?
O4 N2 C3 C2 -137.0(3) . . . . ?
O3 N2 C3 C4 -135.7(3) . . . . ?
O3 N2 C3 C2 43.6(4) . . . . ?
O2 N1 C7 C2 -48.9(5) . . . . ?
O2 N1 C7 C6 132.2(4) . . . . ?
N5 C10 C9 C8 11.0(5) . . . . ?
N5 C10 C9 C14 -174.4(3) . . . . ?
O1 N1 C7 C2 130.8(4) . . . . ?
O1 N1 C7 C6 -48.1(5) . . . . ?
N1 C7 C6 F1 -3.4(5) . . . . ?
N1 C7 C6 C5 177.4(3) . . . . ?
N6 C11 C10 N5 -7.7(5) . . . . ?
N6 C11 C10 C9 175.2(3) . . . . ?
N6 C11 C12 C13 -176.4(3) . . . . ?
N3 C4 C3 N2 -2.2(5) . . . . ?
N3 C4 C3 C2 178.6(3) . . . . ?
N3 C4 C5 C6 -179.1(4) . . . . ?
C11 C10 C9 C8 -171.9(3) . . . . ?
C11 C10 C9 C14 2.6(5) . . . . ?
C10 C11 C12 C13 4.4(5) . . . . ?
C10 C9 C14 N4 -177.8(3) . . . . ?
C10 C9 C14 C13 1.6(5) . . . . ?
C4 C5 C6 F1 -179.9(3) . . . . ?
C4 C5 C6 C7 -0.7(5) . . . . ?
C12 C11 C10 N5 171.4(3) . . . . ?
C12 C11 C10 C9 -5.7(5) . . . . ?
C12 C13 C14 N4 176.7(3) . . . . ?
C12 C13 C14 C9 -2.7(5) . . . . ?
C2 C7 C6 F1 177.8(3) . . . . ?
C2 C7 C6 C5 -1.4(5) . . . . ?
C3 C4 C5 C6 3.1(5) . . . . ?
C3 C2 C7 N1 -177.9(3) . . . . ?
C3 C2 C7 C6 0.9(5) . . . . ?
C5 C4 C3 N2 175.6(3) . . . . ?
C5 C4 C3 C2 -3.7(5) . . . . ?
C7 C2 C3 N2 -177.6(3) . . . . ?
C7 C2 C3 C4 1.7(5) . . . . ?
C8 C9 C14 N4 -3.2(5) . . . . ?
C8 C9 C14 C13 176.2(3) . . . . ?
C14 C13 C12 C11 -0.5(5) . . . . ?
C1 C2 C3 N2 7.9(5) . . . . ?
C1 C2 C3 C4 -172.8(3) . . . . ?
C1 C2 C7 N1 -3.4(5) . . . . ?
C1 C2 C7 C6 175.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU
####################################################################### 
# 
# 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_mo_24121393227
_database_code_depnum_ccdc_archive 'CCDC 2412516'
loop_
_audit_author_name
_audit_author_address
'Yujie Yan'
;Southwest University of Science and Technology
China
;
_audit_update_record             
;
2024-12-23 deposited with the CCDC.	2025-12-17 downloaded from the CCDC.
;
_audit_creation_date             2024-12-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H3 F4 N3 O4'
_chemical_formula_sum            'C7 H3 F4 N3 O4'
_chemical_formula_weight         269.12
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.060(4)
_cell_length_b                   16.847(9)
_cell_length_c                   8.157(4)
_cell_angle_alpha                90
_cell_angle_beta                 119.027(12)
_cell_angle_gamma                90
_cell_volume                     968.5(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1345
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.014
_cell_measurement_theta_min      2.418
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.960
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.4452
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1797 before and 0.1066 after correction.
The Ratio of minimum to maximum transmission is 0.5974.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.846
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0702
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7227
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.394
_diffrn_reflns_theta_min         2.418
_diffrn_ambient_temperature      293.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1185
_reflns_number_total             1767
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         1767
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1094
_refine_ls_R_factor_gt           0.0685
_refine_ls_restrained_S_all      1.116
_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)+(0.0363P)²+1.8709P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1635
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.1241(4) 0.64535(16) 0.7761(4) 0.0607(8) Uani 1 1 d . . . . .
F3 F 0.0755(4) 0.60859(18) 0.5051(4) 0.0665(8) Uani 1 1 d . . . . .
F2 F 0.1486(4) 0.52347(16) 0.7258(4) 0.0640(8) Uani 1 1 d . . . . .
O3 O 0.3222(5) 0.4526(2) 0.5363(5) 0.0644(10) Uani 1 1 d . . . . .
O2 O 0.2319(5) 0.7623(2) 0.6343(5) 0.0635(10) Uani 1 1 d . . . . .
O1 O 0.4294(5) 0.8017(2) 0.9160(5) 0.0664(10) Uani 1 1 d . . . . .
O4 O 0.4734(6) 0.4101(2) 0.8219(5) 0.0722(11) Uani 1 1 d . . . . .
N1 N 0.7756(7) 0.7579(3) 0.9670(8) 0.0795(16) Uani 1 1 d . . . . .
C1 C 0.6823(6) 0.6889(3) 0.9024(6) 0.0502(11) Uani 1 1 d . . . . .
C2 C 0.4852(6) 0.6806(2) 0.8179(6) 0.0409(10) Uani 1 1 d . . . . .
C3 C 0.3948(6) 0.6074(2) 0.7533(5) 0.0396(10) Uani 1 1 d . . . . .
C4 C 0.5047(6) 0.5422(3) 0.7690(6) 0.0421(10) Uani 1 1 d . . . . .
N3 N 0.4252(6) 0.4622(2) 0.7037(6) 0.0497(10) Uani 1 1 d . . . . .
N2 N 0.3737(5) 0.7530(2) 0.7883(6) 0.0493(9) Uani 1 1 d . . . . .
C6 C 0.7891(6) 0.6205(3) 0.9151(7) 0.0559(13) Uani 1 1 d . . . . .
H6 H 0.920401 0.623547 0.969115 0.067 Uiso 1 1 calc R . . . .
C5 C 0.6993(6) 0.5504(3) 0.8484(6) 0.0496(11) Uani 1 1 d . . . . .
C10 C 0.1844(6) 0.5967(3) 0.6875(6) 0.0468(11) Uani 1 1 d . . . . .
F4 F 0.8011(4) 0.48558(18) 0.8560(4) 0.0716(9) Uani 1 1 d . . . . .
H1A H 0.891(8) 0.754(3) 1.004(7) 0.069(17) Uiso 1 1 d . . . . .
H1B H 0.722(8) 0.801(3) 0.979(8) 0.074(19) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C10 1.330(5) . ?
F3 C10 1.325(5) . ?
F2 C10 1.339(5) . ?
O3 N3 1.217(5) . ?
O2 N2 1.231(5) . ?
O1 N2 1.227(5) . ?
O4 N3 1.219(5) . ?
N1 C1 1.346(6) . ?
N1 H1A 0.83(5) . ?
N1 H1B 0.88(5) . ?
C1 C2 1.399(6) . ?
C1 C6 1.412(6) . ?
C2 C3 1.400(6) . ?
C2 N2 1.463(5) . ?
C3 C4 1.378(6) . ?
C3 C10 1.521(6) . ?
C4 N3 1.475(6) . ?
C4 C5 1.383(6) . ?
C6 H6 0.9300 . ?
C6 C5 1.353(6) . ?
C5 F4 1.349(5) . ?

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 H1A 113(4) . . ?
C1 N1 H1B 123(4) . . ?
H1A N1 H1B 123(5) . . ?
N1 C1 C2 124.3(5) . . ?
N1 C1 C6 118.2(5) . . ?
C2 C1 C6 117.5(4) . . ?
C1 C2 C3 122.2(4) . . ?
C1 C2 N2 117.3(4) . . ?
C3 C2 N2 120.4(4) . . ?
C2 C3 C10 121.6(4) . . ?
C4 C3 C2 118.3(4) . . ?
C4 C3 C10 119.7(4) . . ?
C3 C4 N3 123.2(4) . . ?
C3 C4 C5 119.7(4) . . ?
C5 C4 N3 117.1(4) . . ?
O3 N3 O4 125.0(4) . . ?
O3 N3 C4 117.9(4) . . ?
O4 N3 C4 117.1(4) . . ?
O2 N2 C2 117.8(4) . . ?
O1 N2 O2 123.9(4) . . ?
O1 N2 C2 118.3(4) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 C1 119.7(4) . . ?
C5 C6 H6 120.2 . . ?
C6 C5 C4 122.7(4) . . ?
F4 C5 C4 117.8(4) . . ?
F4 C5 C6 119.6(4) . . ?
F1 C10 F2 105.3(3) . . ?
F1 C10 C3 112.0(4) . . ?
F3 C10 F1 107.4(4) . . ?
F3 C10 F2 107.5(4) . . ?
F3 C10 C3 113.4(4) . . ?
F2 C10 C3 110.9(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -179.8(5) . . . . ?
N1 C1 C2 N2 3.8(7) . . . . ?
N1 C1 C6 C5 -178.8(5) . . . . ?
C1 C2 C3 C4 -2.1(6) . . . . ?
C1 C2 C3 C10 171.1(4) . . . . ?
C1 C2 N2 O2 134.0(4) . . . . ?
C1 C2 N2 O1 -44.0(6) . . . . ?
C1 C6 C5 C4 -0.9(7) . . . . ?
C1 C6 C5 F4 178.2(4) . . . . ?
C2 C1 C6 C5 -0.7(7) . . . . ?
C2 C3 C4 N3 -179.2(4) . . . . ?
C2 C3 C4 C5 0.5(6) . . . . ?
C2 C3 C10 F1 -30.1(6) . . . . ?
C2 C3 C10 F3 91.6(5) . . . . ?
C2 C3 C10 F2 -147.4(4) . . . . ?
C3 C2 N2 O2 -42.4(6) . . . . ?
C3 C2 N2 O1 139.7(4) . . . . ?
C3 C4 N3 O3 65.1(6) . . . . ?
C3 C4 N3 O4 -117.3(5) . . . . ?
C3 C4 C5 C6 1.0(7) . . . . ?
C3 C4 C5 F4 -178.1(4) . . . . ?
C4 C3 C10 F1 143.0(4) . . . . ?
C4 C3 C10 F3 -95.3(5) . . . . ?
C4 C3 C10 F2 25.7(5) . . . . ?
N3 C4 C5 C6 -179.3(4) . . . . ?
N3 C4 C5 F4 1.6(6) . . . . ?
N2 C2 C3 C4 174.2(4) . . . . ?
N2 C2 C3 C10 -12.7(6) . . . . ?
C6 C1 C2 C3 2.2(7) . . . . ?
C6 C1 C2 N2 -174.2(4) . . . . ?
C5 C4 N3 O3 -114.6(5) . . . . ?
C5 C4 N3 O4 63.1(5) . . . . ?
C10 C3 C4 N3 7.5(6) . . . . ?
C10 C3 C4 C5 -172.8(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
