# 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 2022

####################################################################### 
# 
# 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_check
_database_code_depnum_ccdc_archive 'CCDC 2159820'
loop_
_audit_author_name
_audit_author_address
'Bu Bufanzhi'
;Ocean University of China
China
;
_audit_update_record             
;
2022-03-17 deposited with the CCDC.	2022-12-07 downloaded from the CCDC.
;
_audit_creation_date             2021-12-29
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H4 F N3 O, C9 H8 O3'
_chemical_formula_sum            'C13 H12 F N3 O4'
_chemical_formula_weight         293.26
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.4654(4)
_cell_length_b                   7.2568(4)
_cell_length_c                   13.7654(8)
_cell_angle_alpha                83.050(2)
_cell_angle_beta                 81.814(2)
_cell_angle_gamma                87.445(2)
_cell_volume                     634.32(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10255
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.512
_cell_measurement_theta_min      3.025
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.943
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.475
_exptl_crystal_size_mid          0.257
_exptl_crystal_size_min          0.138
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13335
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.512
_diffrn_reflns_theta_min         3.010
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  Bruker
_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                2453
_reflns_number_total             2917
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       0.23(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         2917
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0394
_refine_ls_restrained_S_all      1.079
_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)+(0.0841P)²+0.0529P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1285
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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 1.71197(11) -0.14632(11) 0.26481(5) 0.0430(2) Uani 1 1 d . . . . .
O1 O 0.93775(13) 0.09719(13) 0.37967(6) 0.0370(3) Uani 1 1 d . . . . .
N1 N 1.23996(16) -0.04049(15) 0.41781(7) 0.0336(3) Uani 1 1 d . . . . .
N2 N 1.19743(14) 0.05654(13) 0.25247(6) 0.0277(2) Uani 1 1 d . . . . .
N3 N 1.46866(17) 0.01145(16) 0.12952(7) 0.0356(3) Uani 1 1 d . . . . .
C1 C 1.11775(17) 0.04125(16) 0.34970(8) 0.0277(3) Uani 1 1 d . . . . .
C2 C 1.39276(17) -0.00377(15) 0.22405(8) 0.0271(3) Uani 1 1 d . . . . .
C3 C 1.51748(17) -0.08528(16) 0.29621(8) 0.0299(3) Uani 1 1 d . . . . .
C4 C 1.43848(19) -0.10412(18) 0.39132(9) 0.0334(3) Uani 1 1 d . . . . .
O2 O -0.19857(13) 0.82037(14) 0.00280(6) 0.0456(3) Uani 1 1 d . . . . .
O3 O 0.05728(14) 0.80666(15) -0.12306(6) 0.0441(3) Uani 1 1 d . . . . .
O4 O 0.60411(17) 0.33508(15) 0.40392(7) 0.0486(3) Uani 1 1 d . . . . .
C5 C -0.01933(18) 0.77964(16) -0.02886(8) 0.0317(3) Uani 1 1 d . . . . .
C6 C 0.13477(19) 0.69584(18) 0.03342(9) 0.0359(3) Uani 1 1 d . . . . .
C7 C 0.08721(19) 0.65478(16) 0.12991(9) 0.0321(3) Uani 1 1 d . . . . .
C8 C 0.22501(18) 0.57013(15) 0.19928(8) 0.0302(3) Uani 1 1 d . . . . .
C9 C 0.15226(19) 0.54534(17) 0.30042(9) 0.0338(3) Uani 1 1 d . . . . .
C10 C 0.2797(2) 0.46742(18) 0.36828(9) 0.0367(3) Uani 1 1 d . . . . .
C11 C 0.48266(19) 0.41066(16) 0.33521(9) 0.0326(3) Uani 1 1 d . . . . .
C12 C 0.55742(19) 0.43296(17) 0.23529(9) 0.0356(3) Uani 1 1 d . . . . .
C13 C 0.4297(2) 0.51280(18) 0.16868(9) 0.0362(3) Uani 1 1 d . . . . .
H1 H 1.180(2) -0.055(2) 0.4822(13) 0.047(4) Uiso 1 1 d . . . . .
H3 H -0.053(3) 0.854(3) -0.1607(15) 0.071(6) Uiso 1 1 d . . . . .
H3A H 1.593(3) -0.030(2) 0.1112(12) 0.048(4) Uiso 1 1 d . . . . .
H3B H 1.382(3) 0.067(2) 0.0854(13) 0.054(4) Uiso 1 1 d . . . . .
H4A H 1.512(3) -0.165(2) 0.4406(12) 0.052(4) Uiso 1 1 d . . . . .
H4 H 0.717(4) 0.277(3) 0.3775(17) 0.090(7) Uiso 1 1 d . . . . .
H6 H 0.271(3) 0.672(2) 0.0016(12) 0.047(4) Uiso 1 1 d . . . . .
H7 H -0.046(3) 0.685(2) 0.1571(12) 0.044(4) Uiso 1 1 d . . . . .
H9 H 0.010(3) 0.580(2) 0.3257(11) 0.045(4) Uiso 1 1 d . . . . .
H10 H 0.231(3) 0.450(2) 0.4393(13) 0.055(4) Uiso 1 1 d . . . . .
H12 H 0.699(3) 0.393(2) 0.2133(12) 0.053(4) Uiso 1 1 d . . . . .
H13 H 0.491(3) 0.526(2) 0.0998(13) 0.051(4) 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 C3 1.3439(13) . ?
O1 C1 1.2454(14) . ?
N1 C1 1.3747(14) . ?
N1 C4 1.3595(15) . ?
N1 H1 0.911(18) . ?
N2 C1 1.3572(14) . ?
N2 C2 1.3383(14) . ?
N3 C2 1.3170(15) . ?
N3 H3A 0.857(18) . ?
N3 H3B 0.927(18) . ?
C2 C3 1.4249(16) . ?
C3 C4 1.3290(17) . ?
C4 H4A 0.941(17) . ?
O2 C5 1.2153(14) . ?
O3 C5 1.3150(14) . ?
O3 H3 0.96(2) . ?
O4 C11 1.3637(14) . ?
O4 H4 0.88(3) . ?
C5 C6 1.4698(16) . ?
C6 C7 1.3205(17) . ?
C6 H6 0.945(17) . ?
C7 C8 1.4610(15) . ?
C7 H7 0.919(16) . ?
C8 C9 1.3972(16) . ?
C8 C13 1.3917(17) . ?
C9 C10 1.3861(17) . ?
C9 H9 0.969(17) . ?
C10 C11 1.3877(18) . ?
C10 H10 0.978(18) . ?
C11 C12 1.3840(18) . ?
C12 C13 1.3793(17) . ?
C12 H12 0.966(18) . ?
C13 H13 0.970(18) . ?

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 H1 116.8(10) . . ?
C4 N1 C1 122.35(10) . . ?
C4 N1 H1 120.8(10) . . ?
C2 N2 C1 120.36(9) . . ?
C2 N3 H3A 119.9(10) . . ?
C2 N3 H3B 117.1(11) . . ?
H3A N3 H3B 123.0(15) . . ?
O1 C1 N1 118.65(10) . . ?
O1 C1 N2 122.63(10) . . ?
N2 C1 N1 118.72(10) . . ?
N2 C2 C3 119.84(10) . . ?
N3 C2 N2 119.93(10) . . ?
N3 C2 C3 120.23(10) . . ?
F1 C3 C2 118.15(10) . . ?
C4 C3 F1 121.85(10) . . ?
C4 C3 C2 119.97(11) . . ?
N1 C4 H4A 118.8(10) . . ?
C3 C4 N1 118.73(11) . . ?
C3 C4 H4A 122.4(10) . . ?
C5 O3 H3 109.2(12) . . ?
C11 O4 H4 112.6(15) . . ?
O2 C5 O3 123.24(11) . . ?
O2 C5 C6 123.93(10) . . ?
O3 C5 C6 112.82(10) . . ?
C5 C6 H6 117.3(10) . . ?
C7 C6 C5 122.08(11) . . ?
C7 C6 H6 120.6(10) . . ?
C6 C7 C8 127.25(11) . . ?
C6 C7 H7 116.9(10) . . ?
C8 C7 H7 115.9(10) . . ?
C9 C8 C7 119.82(11) . . ?
C13 C8 C7 122.40(11) . . ?
C13 C8 C9 117.78(11) . . ?
C8 C9 H9 121.2(9) . . ?
C10 C9 C8 121.26(11) . . ?
C10 C9 H9 117.5(9) . . ?
C9 C10 C11 119.47(11) . . ?
C9 C10 H10 122.2(10) . . ?
C11 C10 H10 118.3(10) . . ?
O4 C11 C10 117.99(11) . . ?
O4 C11 C12 121.83(11) . . ?
C12 C11 C10 120.19(11) . . ?
C11 C12 H12 119.3(10) . . ?
C13 C12 C11 119.73(11) . . ?
C13 C12 H12 121.0(10) . . ?
C8 C13 H13 122.5(10) . . ?
C12 C13 C8 121.56(11) . . ?
C12 C13 H13 116.0(10) . . ?

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
F1 C3 C4 N1 -179.48(10) . . . . ?
N2 C2 C3 F1 179.20(9) . . . . ?
N2 C2 C3 C4 1.15(18) . . . . ?
N3 C2 C3 F1 -0.43(17) . . . . ?
N3 C2 C3 C4 -178.48(11) . . . . ?
C1 N1 C4 C3 0.50(19) . . . . ?
C1 N2 C2 N3 179.92(10) . . . . ?
C1 N2 C2 C3 0.29(17) . . . . ?
C2 N2 C1 O1 179.22(10) . . . . ?
C2 N2 C1 N1 -1.29(17) . . . . ?
C2 C3 C4 N1 -1.51(19) . . . . ?
C4 N1 C1 O1 -179.56(11) . . . . ?
C4 N1 C1 N2 0.92(18) . . . . ?
O2 C5 C6 C7 1.4(2) . . . . ?
O3 C5 C6 C7 -178.80(12) . . . . ?
O4 C11 C12 C13 -178.99(12) . . . . ?
C5 C6 C7 C8 179.39(11) . . . . ?
C6 C7 C8 C9 176.46(13) . . . . ?
C6 C7 C8 C13 -3.2(2) . . . . ?
C7 C8 C9 C10 -179.26(11) . . . . ?
C7 C8 C13 C12 -179.94(11) . . . . ?
C8 C9 C10 C11 -0.8(2) . . . . ?
C9 C8 C13 C12 0.4(2) . . . . ?
C9 C10 C11 O4 179.80(11) . . . . ?
C9 C10 C11 C12 0.4(2) . . . . ?
C10 C11 C12 C13 0.3(2) . . . . ?
C11 C12 C13 C8 -0.8(2) . . . . ?
C13 C8 C9 C10 0.41(19) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
