# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2090877'
loop_
_audit_author_name
_audit_author_address
'Necmi Dege'
;Ondokuz Mayis University
Turkey
;
_audit_update_record             
;
2021-06-18 deposited with the CCDC.	2022-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 F N O3'
_chemical_formula_weight         285.27

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'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   6.7305(9)
_cell_length_b                   8.9170(12)
_cell_length_c                   11.7682(15)
_cell_angle_alpha                82.956(11)
_cell_angle_beta                 78.846(11)
_cell_angle_gamma                88.804(11)
_cell_volume                     687.70(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8535
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      35.35

_exptl_crystal_description       prism
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.690
_exptl_crystal_size_mid          0.587
_exptl_crystal_size_min          0.420
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_F_000             296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?

_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.9222
_exptl_absorpt_correction_T_max  0.9723
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_diffrn_ambient_temperature      296(2)
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_voltage           50
_diffrn_source_current           45
_diffrn_source_power             2.25
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    '0.8 mm diameter, multiple pinhole'
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
; 117 frames, detector distance = 55 mm
;
_diffrn_reflns_number            6252
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.074
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2687
_reflns_number_gt                2030
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0631P)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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.189(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2687
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1043
_refine_ls_wR_factor_gt          0.0977
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_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
O1 O 0.61822(16) 0.25165(11) 0.21921(9) 0.0586(3) Uani 1 1 d . . . . .
O2 O 0.74484(18) 0.04738(11) 0.56878(9) 0.0641(3) Uani 1 1 d . . . . .
O3 O 0.65306(18) 0.29168(13) 0.72043(9) 0.0694(3) Uani 1 1 d . . . . .
N1 N 0.79796(16) 0.25085(11) 0.42430(9) 0.0445(3) Uani 1 1 d . . . . .
F1 F 0.0251(2) 0.23124(19) -0.03946(12) 0.1210(5) Uani 1 1 d . . . . .
C16 C 0.79067(18) 0.41070(14) 0.42115(11) 0.0425(3) Uani 1 1 d . . . . .
C7 C 0.7084(2) 0.11784(15) 0.26736(13) 0.0526(3) Uani 1 1 d . . . . .
H7A H 0.764725 0.056659 0.206230 0.063 Uiso 1 1 calc R U . . .
H7B H 0.607804 0.058273 0.324204 0.063 Uiso 1 1 calc R U . . .
C11 C 0.73517(18) 0.45220(15) 0.53391(11) 0.0446(3) Uani 1 1 d . . . . .
C8 C 0.8737(2) 0.16784(16) 0.32494(12) 0.0507(3) Uani 1 1 d . . . . .
H8A H 0.946765 0.079503 0.351277 0.061 Uiso 1 1 calc R U . . .
H8B H 0.968676 0.231549 0.267575 0.061 Uiso 1 1 calc R U . . .
C10 C 0.7025(2) 0.31280(16) 0.61537(12) 0.0484(3) Uani 1 1 d . . . . .
C9 C 0.7487(2) 0.18260(15) 0.53675(12) 0.0469(3) Uani 1 1 d . . . . .
C15 C 0.8306(2) 0.51843(15) 0.32449(13) 0.0520(3) Uani 1 1 d . . . . .
H15 H 0.866010 0.491259 0.249408 0.062 Uiso 1 1 calc R U . . .
C4 C 0.4676(2) 0.23546(17) 0.15743(11) 0.0519(3) Uani 1 1 d . . . . .
C14 C 0.8154(2) 0.66992(16) 0.34460(15) 0.0595(4) Uani 1 1 d . . . . .
H14 H 0.842667 0.744561 0.281112 0.071 Uiso 1 1 calc R U . . .
C12 C 0.7197(2) 0.60402(16) 0.55171(14) 0.0544(4) Uani 1 1 d . . . . .
H12 H 0.682326 0.631680 0.626554 0.065 Uiso 1 1 calc R U . . .
C13 C 0.7612(2) 0.71294(16) 0.45550(15) 0.0608(4) Uani 1 1 d . . . . .
H13 H 0.752715 0.814890 0.465477 0.073 Uiso 1 1 calc R U . . .
C3 C 0.3840(3) 0.37094(19) 0.11589(14) 0.0638(4) Uani 1 1 d . . . . .
H3 H 0.427872 0.462319 0.132963 0.077 Uiso 1 1 calc R U . . .
C5 C 0.3967(2) 0.09775(19) 0.13633(13) 0.0614(4) Uani 1 1 d . . . . .
H5 H 0.448523 0.007224 0.166429 0.074 Uiso 1 1 calc R U . . .
C6 C 0.2469(3) 0.0977(2) 0.06948(15) 0.0747(5) Uani 1 1 d . . . . .
H6 H 0.198204 0.006967 0.053989 0.090 Uiso 1 1 calc R U . . .
C1 C 0.1720(3) 0.2326(3) 0.02680(15) 0.0779(5) Uani 1 1 d . . . . .
C2 C 0.2358(3) 0.3694(2) 0.04934(15) 0.0778(5) Uani 1 1 d . . . . .
H2 H 0.180496 0.459116 0.020415 0.093 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
O1 C4 1.3762(17) . ?
O1 C7 1.4319(17) . ?
O2 C9 1.2177(16) . ?
O3 C10 1.2088(17) . ?
N1 C9 1.3684(17) . ?
N1 C16 1.4214(16) . ?
N1 C8 1.4632(17) . ?
F1 C1 1.374(2) . ?
C16 C15 1.3832(19) . ?
C16 C11 1.4000(19) . ?
C7 C8 1.511(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C11 C12 1.3938(19) . ?
C11 C10 1.4663(19) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C10 C9 1.561(2) . ?
C15 C14 1.398(2) . ?
C15 H15 0.9300 . ?
C4 C5 1.394(2) . ?
C4 C3 1.396(2) . ?
C14 C13 1.384(2) . ?
C14 H14 0.9300 . ?
C12 C13 1.387(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C3 C2 1.383(2) . ?
C3 H3 0.9300 . ?
C5 C6 1.394(2) . ?
C5 H5 0.9300 . ?
C6 C1 1.370(3) . ?
C6 H6 0.9300 . ?
C1 C2 1.374(3) . ?
C2 H2 0.9300 . ?

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
C4 O1 C7 118.22(11) . . ?
C9 N1 C16 110.63(10) . . ?
C9 N1 C8 123.14(11) . . ?
C16 N1 C8 125.73(11) . . ?
C15 C16 C11 121.22(12) . . ?
C15 C16 N1 128.01(12) . . ?
C11 C16 N1 110.77(11) . . ?
O1 C7 C8 107.18(11) . . ?
O1 C7 H7A 110.3 . . ?
C8 C7 H7A 110.3 . . ?
O1 C7 H7B 110.3 . . ?
C8 C7 H7B 110.3 . . ?
H7A C7 H7B 108.5 . . ?
C12 C11 C16 120.64(12) . . ?
C12 C11 C10 131.85(13) . . ?
C16 C11 C10 107.51(11) . . ?
N1 C8 C7 113.38(11) . . ?
N1 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
N1 C8 H8B 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
O3 C10 C11 131.62(13) . . ?
O3 C10 C9 123.53(13) . . ?
C11 C10 C9 104.85(11) . . ?
O2 C9 N1 126.68(13) . . ?
O2 C9 C10 127.08(12) . . ?
N1 C9 C10 106.23(11) . . ?
C16 C15 C14 117.09(14) . . ?
C16 C15 H15 121.5 . . ?
C14 C15 H15 121.5 . . ?
O1 C4 C5 124.95(14) . . ?
O1 C4 C3 114.74(13) . . ?
C5 C4 C3 120.30(15) . . ?
C13 C14 C15 122.43(14) . . ?
C13 C14 H14 118.8 . . ?
C15 C14 H14 118.8 . . ?
C13 C12 C11 118.61(14) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C14 C13 C12 119.99(14) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C2 C3 C4 120.04(16) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C6 C5 C4 119.04(16) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C1 C6 C5 119.34(17) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6 C1 F1 118.88(19) . . ?
C6 C1 C2 122.50(17) . . ?
F1 C1 C2 118.6(2) . . ?
C1 C2 C3 118.70(18) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?

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
C9 N1 C16 C15 179.90(13) . . . . ?
C8 N1 C16 C15 7.8(2) . . . . ?
C9 N1 C16 C11 -0.02(14) . . . . ?
C8 N1 C16 C11 -172.10(11) . . . . ?
C4 O1 C7 C8 177.37(11) . . . . ?
C15 C16 C11 C12 -0.34(19) . . . . ?
N1 C16 C11 C12 179.59(11) . . . . ?
C15 C16 C11 C10 179.56(12) . . . . ?
N1 C16 C11 C10 -0.51(14) . . . . ?
C9 N1 C8 C7 91.95(15) . . . . ?
C16 N1 C8 C7 -96.92(14) . . . . ?
O1 C7 C8 N1 64.46(14) . . . . ?
C12 C11 C10 O3 0.0(3) . . . . ?
C16 C11 C10 O3 -179.84(15) . . . . ?
C12 C11 C10 C9 -179.34(13) . . . . ?
C16 C11 C10 C9 0.77(13) . . . . ?
C16 N1 C9 O2 -178.51(13) . . . . ?
C8 N1 C9 O2 -6.2(2) . . . . ?
C16 N1 C9 C10 0.51(14) . . . . ?
C8 N1 C9 C10 172.83(11) . . . . ?
O3 C10 C9 O2 -1.2(2) . . . . ?
C11 C10 C9 O2 178.22(13) . . . . ?
O3 C10 C9 N1 179.76(13) . . . . ?
C11 C10 C9 N1 -0.79(13) . . . . ?
C11 C16 C15 C14 0.73(19) . . . . ?
N1 C16 C15 C14 -179.18(12) . . . . ?
C7 O1 C4 C5 -0.90(19) . . . . ?
C7 O1 C4 C3 178.45(12) . . . . ?
C16 C15 C14 C13 -0.6(2) . . . . ?
C16 C11 C12 C13 -0.26(19) . . . . ?
C10 C11 C12 C13 179.87(14) . . . . ?
C15 C14 C13 C12 0.0(2) . . . . ?
C11 C12 C13 C14 0.4(2) . . . . ?
O1 C4 C3 C2 177.92(13) . . . . ?
C5 C4 C3 C2 -2.7(2) . . . . ?
O1 C4 C5 C6 -178.22(13) . . . . ?
C3 C4 C5 C6 2.5(2) . . . . ?
C4 C5 C6 C1 -0.4(2) . . . . ?
C5 C6 C1 F1 179.69(15) . . . . ?
C5 C6 C1 C2 -1.4(3) . . . . ?
C6 C1 C2 C3 1.2(3) . . . . ?
F1 C1 C2 C3 -179.90(15) . . . . ?
C4 C3 C2 C1 0.9(3) . . . . ?

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
_geom_hbond_publ_flag
C7 H7B O2 0.97 2.60 3.5228(19) 159.3 2_656 yes
C8 H8A O2 0.97 2.62 3.5050(19) 151.6 2_756 yes

_refine_diff_density_max         0.157
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.042

