# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_A
_database_code_depnum_ccdc_archive 'CCDC 2056661'
loop_
_audit_author_name
_audit_author_address
'Mu-Jia Luo'
;hunan university
China
;
_audit_update_record             
;
2021-01-17 deposited with the CCDC.	2021-10-12 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         C15H13FN2O3
_chemical_formula_sum            'C15 H13 F N2 O3'
_chemical_formula_weight         288.27

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/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   12.35(3)
_cell_length_b                   13.16(3)
_cell_length_c                   8.567(18)
_cell_angle_alpha                90
_cell_angle_beta                 93.00(3)
_cell_angle_gamma                90
_cell_volume                     1390(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1475
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      28.56

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   0.7512
_exptl_transmission_factor_max   1.0000
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7959
_diffrn_reflns_av_unetI/netI     0.2062
_diffrn_reflns_av_R_equivalents  0.2033
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.263
_diffrn_reflns_theta_max         25.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             2498
_reflns_number_gt                923
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0694P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2498
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2881
_refine_ls_R_factor_gt           0.1215
_refine_ls_wR_factor_ref         0.2314
_refine_ls_wR_factor_gt          0.1976
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_restrained_S_all      1.160
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.9486(3) 0.1731(3) -0.2730(4) 0.0643(12) Uani 1 1 d . . . . .
N2 N 0.6038(4) 0.2337(4) 0.0930(5) 0.0322(13) Uani 1 1 d . . . . .
N1 N 0.6452(5) 0.0686(4) 0.0384(6) 0.0471(15) Uani 1 1 d . . . . .
O1 O 0.9100(4) 0.3629(4) -0.2096(5) 0.0573(14) Uani 1 1 d . . . . .
C6 C 0.6934(5) 0.2368(5) 0.0010(7) 0.0336(16) Uani 1 1 d . . . . .
C8 C 0.5452(5) 0.3098(5) 0.1597(7) 0.0372(17) Uani 1 1 d . . . . .
H8 H 0.5645 0.3772 0.1442 0.045 Uiso 1 1 calc R U . . .
C9 C 0.5780(5) 0.1294(5) 0.1138(7) 0.0384(17) Uani 1 1 d . . . . .
C7 C 0.7537(5) 0.3187(5) -0.0561(6) 0.0371(17) Uani 1 1 d . . . . .
H7 H 0.7357 0.3858 -0.0346 0.044 Uiso 1 1 calc R U . . .
O2 O 0.3146(4) 0.0665(4) 0.4072(5) 0.0698(16) Uani 1 1 d . . . . .
C13 C 0.3383(6) 0.1536(6) 0.3700(8) 0.049(2) Uani 1 1 d . . . . .
O3 O 0.2794(4) 0.2346(3) 0.4115(5) 0.0505(13) Uani 1 1 d . . . . .
C12 C 0.4593(5) 0.2882(5) 0.2480(7) 0.0370(17) Uani 1 1 d . . . . .
H12 H 0.4201 0.3404 0.2917 0.044 Uiso 1 1 calc R U . . .
C3 C 0.8618(5) 0.1912(5) -0.1804(7) 0.0411(18) Uani 1 1 d . . . . .
C10 C 0.4890(5) 0.1069(5) 0.2049(7) 0.0466(19) Uani 1 1 d . . . . .
H10 H 0.4696 0.0394 0.2196 0.056 Uiso 1 1 calc R U . . .
C4 C 0.8052(6) 0.1119(5) -0.1260(7) 0.051(2) Uani 1 1 d . . . . .
H4 H 0.8232 0.0453 -0.1500 0.062 Uiso 1 1 calc R U . . .
C2 C 0.8398(5) 0.2955(5) -0.1447(7) 0.0401(18) Uani 1 1 d . . . . .
C11 C 0.4299(5) 0.1831(5) 0.2730(7) 0.0388(18) Uani 1 1 d . . . . .
C15 C 0.1380(6) 0.3214(6) 0.5396(8) 0.071(2) Uani 1 1 d . . . . .
H15A H 0.1922 0.3622 0.5942 0.107 Uiso 1 1 calc R U . . .
H15B H 0.0770 0.3131 0.6035 0.107 Uiso 1 1 calc R U . . .
H15C H 0.1148 0.3544 0.4436 0.107 Uiso 1 1 calc R U . . .
C14 C 0.1853(6) 0.2179(6) 0.5039(8) 0.061(2) Uani 1 1 d . . . . .
H14A H 0.2066 0.1828 0.6003 0.073 Uiso 1 1 calc R U . . .
H14B H 0.1319 0.1767 0.4459 0.073 Uiso 1 1 calc R U . . .
C5 C 0.7170(5) 0.1340(5) -0.0308(7) 0.0377(17) Uani 1 1 d . . . . .
C1 C 0.8876(6) 0.4689(5) -0.1855(8) 0.074(3) Uani 1 1 d . . . . .
H1A H 0.8160 0.4844 -0.2278 0.111 Uiso 1 1 calc R U . . .
H1B H 0.9396 0.5094 -0.2370 0.111 Uiso 1 1 calc R U . . .
H1C H 0.8921 0.4835 -0.0755 0.111 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
F1 C3 1.388(7) . ?
N2 C8 1.377(7) . ?
N2 C6 1.391(7) . ?
N2 C9 1.423(8) . ?
N1 C9 1.342(7) . ?
N1 C5 1.390(7) . ?
O1 C2 1.378(7) . ?
O1 C1 1.438(8) . ?
C6 C7 1.413(8) . ?
C6 C5 1.413(8) . ?
C8 C12 1.364(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.413(8) . ?
C7 C2 1.374(8) . ?
C7 H7 0.9300 . ?
O2 C13 1.230(8) . ?
C13 O3 1.348(8) . ?
C13 C11 1.490(9) . ?
O3 C14 1.457(7) . ?
C12 C11 1.449(8) . ?
C12 H12 0.9300 . ?
C3 C4 1.352(8) . ?
C3 C2 1.435(9) . ?
C10 C11 1.386(8) . ?
C10 H10 0.9300 . ?
C4 C5 1.425(8) . ?
C4 H4 0.9300 . ?
C15 C14 1.519(9) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

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
C8 N2 C6 131.7(5) . . ?
C8 N2 C9 121.5(5) . . ?
C6 N2 C9 106.8(5) . . ?
C9 N1 C5 105.1(5) . . ?
C2 O1 C1 115.9(5) . . ?
N2 C6 C7 131.8(6) . . ?
N2 C6 C5 105.1(6) . . ?
C7 C6 C5 123.1(6) . . ?
C12 C8 N2 121.3(6) . . ?
C12 C8 H8 119.3 . . ?
N2 C8 H8 119.3 . . ?
N1 C9 C10 131.3(6) . . ?
N1 C9 N2 111.5(6) . . ?
C10 C9 N2 117.2(6) . . ?
C2 C7 C6 117.3(6) . . ?
C2 C7 H7 121.3 . . ?
C6 C7 H7 121.3 . . ?
O2 C13 O3 121.9(7) . . ?
O2 C13 C11 125.8(7) . . ?
O3 C13 C11 112.2(6) . . ?
C13 O3 C14 118.8(6) . . ?
C8 C12 C11 119.2(6) . . ?
C8 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C4 C3 F1 119.6(6) . . ?
C4 C3 C2 124.0(7) . . ?
F1 C3 C2 116.5(6) . . ?
C11 C10 C9 121.5(6) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C3 C4 C5 117.6(6) . . ?
C3 C4 H4 121.2 . . ?
C5 C4 H4 121.2 . . ?
C7 C2 O1 127.0(6) . . ?
C7 C2 C3 119.4(6) . . ?
O1 C2 C3 113.6(6) . . ?
C10 C11 C12 119.2(6) . . ?
C10 C11 C13 118.6(6) . . ?
C12 C11 C13 122.3(6) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O3 C14 C15 107.5(6) . . ?
O3 C14 H14A 110.2 . . ?
C15 C14 H14A 110.2 . . ?
O3 C14 H14B 110.2 . . ?
C15 C14 H14B 110.2 . . ?
H14A C14 H14B 108.5 . . ?
N1 C5 C6 111.5(6) . . ?
N1 C5 C4 129.9(6) . . ?
C6 C5 C4 118.5(6) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 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
C8 N2 C6 C7 -0.7(10) . . . . ?
C9 N2 C6 C7 -179.8(6) . . . . ?
C8 N2 C6 C5 179.7(6) . . . . ?
C9 N2 C6 C5 0.5(6) . . . . ?
C6 N2 C8 C12 -179.5(6) . . . . ?
C9 N2 C8 C12 -0.4(8) . . . . ?
C5 N1 C9 C10 -179.9(6) . . . . ?
C5 N1 C9 N2 0.9(7) . . . . ?
C8 N2 C9 N1 179.8(5) . . . . ?
C6 N2 C9 N1 -0.9(6) . . . . ?
C8 N2 C9 C10 0.5(8) . . . . ?
C6 N2 C9 C10 179.8(5) . . . . ?
N2 C6 C7 C2 179.5(6) . . . . ?
C5 C6 C7 C2 -0.9(8) . . . . ?
O2 C13 O3 C14 0.4(9) . . . . ?
C11 C13 O3 C14 178.7(5) . . . . ?
N2 C8 C12 C11 0.5(8) . . . . ?
N1 C9 C10 C11 -179.9(6) . . . . ?
N2 C9 C10 C11 -0.8(9) . . . . ?
F1 C3 C4 C5 179.7(5) . . . . ?
C2 C3 C4 C5 1.6(10) . . . . ?
C6 C7 C2 O1 -178.9(5) . . . . ?
C6 C7 C2 C3 2.6(8) . . . . ?
C1 O1 C2 C7 -2.3(9) . . . . ?
C1 O1 C2 C3 176.3(5) . . . . ?
C4 C3 C2 C7 -3.1(10) . . . . ?
F1 C3 C2 C7 178.7(5) . . . . ?
C4 C3 C2 O1 178.2(6) . . . . ?
F1 C3 C2 O1 0.0(8) . . . . ?
C9 C10 C11 C12 0.9(9) . . . . ?
C9 C10 C11 C13 -178.9(6) . . . . ?
C8 C12 C11 C10 -0.7(9) . . . . ?
C8 C12 C11 C13 179.0(6) . . . . ?
O2 C13 C11 C10 6.4(10) . . . . ?
O3 C13 C11 C10 -171.8(5) . . . . ?
O2 C13 C11 C12 -173.4(6) . . . . ?
O3 C13 C11 C12 8.4(8) . . . . ?
C13 O3 C14 C15 177.4(6) . . . . ?
C9 N1 C5 C6 -0.5(7) . . . . ?
C9 N1 C5 C4 -179.6(6) . . . . ?
N2 C6 C5 N1 0.0(6) . . . . ?
C7 C6 C5 N1 -179.7(5) . . . . ?
N2 C6 C5 C4 179.1(5) . . . . ?
C7 C6 C5 C4 -0.5(9) . . . . ?
C3 C4 C5 N1 179.2(6) . . . . ?
C3 C4 C5 C6 0.2(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1B F1 0.96 2.56 3.394(9) 145.6 2_754
C1 H1B F1 0.96 2.56 3.394(9) 145.6 2_754
C1 H1B F1 0.96 2.56 3.394(9) 145.6 2_754
C1 H1B F1 0.96 2.56 3.394(9) 145.6 2_754
C1 H1B F1 0.96 2.56 3.394(9) 145.6 2_754
C1 H1B F1 0.96 2.56 3.394(9) 145.6 2_754
C1 H1B F1 0.96 2.56 3.394(9) 145.6 2_754
C1 H1B F1 0.96 2.56 3.394(9) 145.6 2_754
C1 H1B F1 0.96 2.56 3.394(9) 145.6 2_754
C1 H1B F1 0.96 2.56 3.394(9) 145.6 2_754
C1 H1B F1 0.96 2.56 3.394(9) 145.6 2_754

_refine_diff_density_max         0.286
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.082

