# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_1
_database_code_depnum_ccdc_archive 'CCDC 2063557'
loop_
_audit_author_name
_audit_author_address
'Jin Yang'
;Huaibei Normal University
China
;
_audit_update_record             
;
2021-02-18 deposited with the CCDC.	2021-06-07 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         ?
_chemical_formula_sum            'C15 H13 F N2 O2'
_chemical_formula_weight         272.27

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                   4.5093(13)
_cell_length_b                   10.415(3)
_cell_length_c                   15.589(4)
_cell_angle_alpha                70.49
_cell_angle_beta                 87.920(4)
_cell_angle_gamma                83.761(5)
_cell_volume                     686.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1715
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      30.18

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_F_000             284
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3473
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_av_R_equivalents  0.0143
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.086
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_full        24.992
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2396
_reflns_number_gt                1677
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_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)+(0.0296P)²+1.7456P] 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         2396
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.1228
_refine_ls_wR_factor_gt          0.1132
_refine_ls_goodness_of_fit_ref   0.691
_refine_ls_restrained_S_all      0.691
_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
F001 F 1.4553(4) 0.07711(18) 0.09928(14) 0.0767(6) Uani 1 1 d . . . . .
O1 O 0.8187(5) 0.2196(2) 0.38367(13) 0.0615(6) Uani 1 1 d . . . . .
N2 N 0.5589(4) 0.3891(2) 0.21252(14) 0.0405(5) Uani 1 1 d . . . . .
N1 N 0.4961(5) 0.5082(2) 0.16024(14) 0.0446(5) Uani 1 1 d . . . . .
O2 O 0.7080(6) 0.0266(2) 0.36748(15) 0.0824(8) Uani 1 1 d . . . . .
C7 C 0.7920(5) 0.3133(2) 0.17980(16) 0.0373(6) Uani 1 1 d . . . . .
C8 C 0.9113(5) 0.1896(2) 0.24195(17) 0.0397(6) Uani 1 1 d . . . . .
C6 C 0.2701(5) 0.5866(3) 0.19337(18) 0.0426(6) Uani 1 1 d . . . . .
C13 C 0.7991(6) 0.1361(3) 0.33720(18) 0.0474(7) Uani 1 1 d . . . . .
C12 C 0.8943(6) 0.3528(3) 0.09065(17) 0.0444(6) Uani 1 1 d . . . . .
H12 H 0.8099 0.4339 0.0486 0.053 Uiso 1 1 calc R U . . .
C9 C 1.1348(6) 0.1094(3) 0.21369(19) 0.0490(7) Uani 1 1 d . . . . .
H9 H 1.2155 0.0261 0.2541 0.059 Uiso 1 1 calc R U . . .
C11 C 1.1180(6) 0.2744(3) 0.06336(19) 0.0501(7) Uani 1 1 d . . . . .
H11 H 1.1885 0.3023 0.0039 0.060 Uiso 1 1 calc R U . . .
C1 C 0.2038(6) 0.7205(3) 0.1378(2) 0.0543(7) Uani 1 1 d . . . . .
H1 H 0.3002 0.7530 0.0821 0.065 Uiso 1 1 calc R U . . .
C10 C 1.2341(6) 0.1544(3) 0.1260(2) 0.0499(7) Uani 1 1 d . . . . .
C5 C 0.1263(6) 0.5381(3) 0.2762(2) 0.0526(7) Uani 1 1 d . . . . .
H5 H 0.1686 0.4477 0.3136 0.063 Uiso 1 1 calc R U . . .
C2 C -0.0057(7) 0.8060(3) 0.1649(3) 0.0657(9) Uani 1 1 d . . . . .
H2 H -0.0518 0.8960 0.1272 0.079 Uiso 1 1 calc R U . . .
C4 C -0.0800(7) 0.6251(3) 0.3027(2) 0.0670(9) Uani 1 1 d . . . . .
H4 H -0.1759 0.5935 0.3586 0.080 Uiso 1 1 calc R U . . .
C3 C -0.1455(7) 0.7589(4) 0.2471(3) 0.0715(10) Uani 1 1 d . . . . .
H3 H -0.2849 0.8171 0.2656 0.086 Uiso 1 1 calc R U . . .
C14 C 0.6927(9) 0.1782(4) 0.4748(2) 0.0804(11) Uani 1 1 d . . . . .
H14A H 0.4902 0.1562 0.4728 0.096 Uiso 1 1 calc R U . . .
H14B H 0.8098 0.0974 0.5137 0.096 Uiso 1 1 calc R U . . .
C15 C 0.6939(12) 0.2890(5) 0.5109(3) 0.1236(18) Uani 1 1 d . . . . .
H15A H 0.5697 0.3673 0.4738 0.185 Uiso 1 1 calc R U . . .
H15B H 0.8940 0.3124 0.5108 0.185 Uiso 1 1 calc R U . . .
H15C H 0.6187 0.2611 0.5721 0.185 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
F001 C10 1.355(3) . ?
O1 C13 1.315(3) . ?
O1 C14 1.454(3) . ?
N2 N1 1.244(3) . ?
N2 C7 1.428(3) . ?
N1 C6 1.427(3) . ?
O2 C13 1.192(3) . ?
C7 C8 1.393(3) . ?
C7 C12 1.388(3) . ?
C8 C9 1.393(4) . ?
C8 C13 1.492(4) . ?
C6 C1 1.380(4) . ?
C6 C5 1.385(4) . ?
C12 C11 1.374(4) . ?
C12 H12 0.9300 . ?
C9 C10 1.365(4) . ?
C9 H9 0.9300 . ?
C11 C10 1.367(4) . ?
C11 H11 0.9300 . ?
C1 C2 1.380(4) . ?
C1 H1 0.9300 . ?
C5 C4 1.378(4) . ?
C5 H5 0.9300 . ?
C2 C3 1.367(5) . ?
C2 H2 0.9300 . ?
C4 C3 1.379(5) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C14 C15 1.443(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C13 O1 C14 116.3(2) . . ?
N1 N2 C7 113.8(2) . . ?
N2 N1 C6 114.4(2) . . ?
C8 C7 C12 119.4(2) . . ?
C8 C7 N2 116.4(2) . . ?
C12 C7 N2 124.1(2) . . ?
C9 C8 C7 119.2(2) . . ?
C9 C8 C13 118.3(2) . . ?
C7 C8 C13 122.4(2) . . ?
C1 C6 C5 120.1(3) . . ?
C1 C6 N1 115.4(2) . . ?
C5 C6 N1 124.5(2) . . ?
O2 C13 O1 124.3(3) . . ?
O2 C13 C8 122.2(3) . . ?
O1 C13 C8 113.5(2) . . ?
C11 C12 C7 121.2(2) . . ?
C11 C12 H12 119.4 . . ?
C7 C12 H12 119.4 . . ?
C10 C9 C8 119.2(2) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C10 C11 C12 118.2(3) . . ?
C10 C11 H11 120.9 . . ?
C12 C11 H11 120.9 . . ?
C2 C1 C6 119.9(3) . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
F001 C10 C11 118.3(3) . . ?
F001 C10 C9 119.0(3) . . ?
C11 C10 C9 122.7(2) . . ?
C4 C5 C6 119.3(3) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C3 C4 C5 120.5(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C15 C14 O1 109.0(3) . . ?
C15 C14 H14A 109.9 . . ?
O1 C14 H14A 109.9 . . ?
C15 C14 H14B 109.9 . . ?
O1 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
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 . . ?

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
C7 N2 N1 C6 -178.1(2) . . . . ?
N1 N2 C7 C8 168.1(2) . . . . ?
N1 N2 C7 C12 -14.5(3) . . . . ?
C12 C7 C8 C9 1.2(4) . . . . ?
N2 C7 C8 C9 178.6(2) . . . . ?
C12 C7 C8 C13 -176.0(2) . . . . ?
N2 C7 C8 C13 1.5(3) . . . . ?
N2 N1 C6 C1 178.0(2) . . . . ?
N2 N1 C6 C5 -0.2(4) . . . . ?
C14 O1 C13 O2 -6.1(4) . . . . ?
C14 O1 C13 C8 175.6(3) . . . . ?
C9 C8 C13 O2 -54.3(4) . . . . ?
C7 C8 C13 O2 122.9(3) . . . . ?
C9 C8 C13 O1 124.1(3) . . . . ?
C7 C8 C13 O1 -58.8(3) . . . . ?
C8 C7 C12 C11 -2.2(4) . . . . ?
N2 C7 C12 C11 -179.4(2) . . . . ?
C7 C8 C9 C10 0.7(4) . . . . ?
C13 C8 C9 C10 178.0(2) . . . . ?
C7 C12 C11 C10 1.3(4) . . . . ?
C5 C6 C1 C2 0.1(4) . . . . ?
N1 C6 C1 C2 -178.1(3) . . . . ?
C12 C11 C10 F001 -179.8(2) . . . . ?
C12 C11 C10 C9 0.6(4) . . . . ?
C8 C9 C10 F001 178.9(2) . . . . ?
C8 C9 C10 C11 -1.6(4) . . . . ?
C1 C6 C5 C4 -0.7(4) . . . . ?
N1 C6 C5 C4 177.3(3) . . . . ?
C6 C1 C2 C3 0.7(5) . . . . ?
C6 C5 C4 C3 0.6(5) . . . . ?
C5 C4 C3 C2 0.1(5) . . . . ?
C1 C2 C3 C4 -0.8(5) . . . . ?
C13 O1 C14 C15 -171.8(3) . . . . ?

_refine_diff_density_max         0.207
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.042

