# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_221113e
_database_code_depnum_ccdc_archive 'CCDC 2254051'
loop_
_audit_author_name
_audit_author_address
'Huai-Wei Wang'
;Liaocheng University
China
;
_audit_update_record             
;
2023-04-05 deposited with the CCDC.	2023-05-30 downloaded from the CCDC.
;
_audit_creation_date             2023-03-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H10 F3 N3 O'
_chemical_formula_sum            'C16 H10 F3 N3 O'
_chemical_formula_weight         317.27
_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                   14.5478(12)
_cell_length_b                   9.6153(8)
_cell_length_c                   10.2086(9)
_cell_angle_alpha                90
_cell_angle_beta                 101.992(4)
_cell_angle_gamma                90
_cell_volume                     1396.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1619
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.218
_cell_measurement_theta_min      2.863
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0591
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6619
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.010
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_min         2.556
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_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                1549
_reflns_number_total             2463
_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 V6.36A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V6.36A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.882
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2463
_refine_ls_number_restraints     630
_refine_ls_R_factor_all          0.1186
_refine_ls_R_factor_gt           0.0770
_refine_ls_restrained_S_all      1.272
_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)+(0.1028P)²+1.7744P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2114
_refine_ls_wR_factor_ref         0.2344
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 3.8A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 3.8A
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
 C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O1 O 0.4988(2) 1.1863(3) 0.7245(3) 0.0444(8) Uani 1 1 d . U . . .
N1 N 0.3723(2) 1.0546(3) 0.6367(3) 0.0309(7) Uani 1 1 d . U . . .
N2 N 0.2672(2) 1.1338(4) 0.7612(3) 0.0417(8) Uani 1 1 d . U . . .
N3 N 0.2047(3) 0.6860(4) 0.6611(4) 0.0506(10) Uani 1 1 d . U . . .
F1 F -0.0669(3) 0.7802(7) 0.4718(5) 0.1461(19) Uani 1 1 d . U . . .
F2 F -0.0173(3) 0.6869(6) 0.3225(6) 0.161(2) Uani 1 1 d . U . . .
F3 F -0.0248(3) 0.8929(5) 0.3284(5) 0.1321(17) Uani 1 1 d . U . . .
C1 C 0.4479(3) 1.1376(4) 0.6245(4) 0.0326(8) Uani 1 1 d . U . . .
C2 C 0.4595(3) 1.1614(4) 0.4918(4) 0.0350(9) Uani 1 1 d . U . . .
H2 H 0.508122 1.218374 0.477652 0.042 Uiso 1 1 calc R U . . .
C3 C 0.4018(3) 1.1036(4) 0.3863(4) 0.0374(9) Uani 1 1 d . U . . .
H3 H 0.409757 1.122710 0.300072 0.045 Uiso 1 1 calc R U . . .
C4 C 0.3297(3) 1.0147(4) 0.4054(4) 0.0376(9) Uani 1 1 d . U . . .
H4 H 0.291515 0.972283 0.331857 0.045 Uiso 1 1 calc R U . . .
C5 C 0.3152(3) 0.9901(4) 0.5275(4) 0.0330(8) Uani 1 1 d . U . . .
C6 C 0.3424(3) 1.0588(4) 0.7626(4) 0.0317(8) Uani 1 1 d . U . . .
C7 C 0.3915(3) 0.9889(5) 0.8711(4) 0.0389(9) Uani 1 1 d . U . . .
H7 H 0.444234 0.936231 0.866095 0.047 Uiso 1 1 calc R U . . .
C8 C 0.3596(3) 0.9996(5) 0.9879(4) 0.0470(11) Uani 1 1 d . U . . .
H8 H 0.390256 0.953514 1.064734 0.056 Uiso 1 1 calc R U . . .
C9 C 0.2826(3) 1.0785(6) 0.9897(5) 0.0508(11) Uani 1 1 d . U . . .
H9 H 0.260608 1.088804 1.068460 0.061 Uiso 1 1 calc R U . . .
C10 C 0.2382(3) 1.1420(5) 0.8761(5) 0.0500(11) Uani 1 1 d . U . . .
H10 H 0.184612 1.193940 0.878344 0.060 Uiso 1 1 calc R U . . .
C11 C 0.2439(3) 0.8897(4) 0.5509(4) 0.0334(8) Uani 1 1 d . U . . .
C12 C 0.1554(3) 0.8915(5) 0.4710(4) 0.0423(10) Uani 1 1 d . U . . .
H12 H 0.138313 0.960457 0.406699 0.051 Uiso 1 1 calc R U . . .
C13 C 0.2649(3) 0.7838(4) 0.6431(4) 0.0395(9) Uani 1 1 d . U . . .
H13 H 0.325214 0.780714 0.695989 0.047 Uiso 1 1 calc R U . . .
C14 C 0.0927(3) 0.7902(5) 0.4875(5) 0.0478(10) Uani 1 1 d . U . . .
C15 C 0.1200(3) 0.6906(5) 0.5827(5) 0.0516(11) Uani 1 1 d . U . . .
H15 H 0.076750 0.622396 0.593130 0.062 Uiso 1 1 calc R U . . .
C16 C -0.0022(4) 0.7868(7) 0.4059(6) 0.0647(13) Uani 1 1 d . 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 C1 1.223(5) . ?
N1 C1 1.385(5) . ?
N1 C5 1.390(5) . ?
N1 C6 1.440(5) . ?
N2 C6 1.308(5) . ?
N2 C10 1.329(5) . ?
N3 C13 1.324(5) . ?
N3 C15 1.324(6) . ?
F1 C16 1.267(6) . ?
F2 C16 1.272(7) . ?
F3 C16 1.291(7) . ?
C1 C2 1.418(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.341(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.398(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.328(5) . ?
C5 C11 1.472(6) . ?
C6 C7 1.364(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.370(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.356(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.351(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.374(6) . ?
C11 C13 1.378(6) . ?
C12 H12 0.9300 . ?
C12 C14 1.368(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.364(7) . ?
C14 C16 1.457(7) . ?
C15 H15 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
C1 N1 C5 122.6(3) . . ?
C1 N1 C6 117.2(3) . . ?
C5 N1 C6 119.1(3) . . ?
C6 N2 C10 116.2(4) . . ?
C13 N3 C15 116.9(4) . . ?
O1 C1 N1 120.0(3) . . ?
O1 C1 C2 124.3(4) . . ?
N1 C1 C2 115.7(3) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 C1 121.4(4) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.3(4) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.6(4) . . ?
C5 C4 H4 119.7 . . ?
N1 C5 C11 119.1(3) . . ?
C4 C5 N1 119.2(4) . . ?
C4 C5 C11 121.6(4) . . ?
N2 C6 N1 114.4(3) . . ?
N2 C6 C7 125.1(4) . . ?
C7 C6 N1 120.5(4) . . ?
C6 C7 H7 121.4 . . ?
C6 C7 C8 117.1(4) . . ?
C8 C7 H7 121.4 . . ?
C7 C8 H8 120.5 . . ?
C9 C8 C7 118.9(4) . . ?
C9 C8 H8 120.5 . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.4(4) . . ?
C10 C9 H9 120.3 . . ?
N2 C10 C9 123.2(4) . . ?
N2 C10 H10 118.4 . . ?
C9 C10 H10 118.4 . . ?
C12 C11 C5 120.1(4) . . ?
C12 C11 C13 117.5(4) . . ?
C13 C11 C5 122.1(4) . . ?
C11 C12 H12 120.5 . . ?
C14 C12 C11 119.0(4) . . ?
C14 C12 H12 120.5 . . ?
N3 C13 C11 124.1(4) . . ?
N3 C13 H13 117.9 . . ?
C11 C13 H13 117.9 . . ?
C12 C14 C16 121.5(5) . . ?
C15 C14 C12 119.0(4) . . ?
C15 C14 C16 119.5(4) . . ?
N3 C15 C14 123.4(4) . . ?
N3 C15 H15 118.3 . . ?
C14 C15 H15 118.3 . . ?
F1 C16 F2 105.9(6) . . ?
F1 C16 F3 104.0(6) . . ?
F1 C16 C14 114.7(5) . . ?
F2 C16 F3 101.5(5) . . ?
F2 C16 C14 114.3(5) . . ?
F3 C16 C14 115.0(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
O1 C1 C2 C3 179.3(4) . . . . ?
N1 C1 C2 C3 -1.7(6) . . . . ?
N1 C5 C11 C12 137.4(4) . . . . ?
N1 C5 C11 C13 -48.8(5) . . . . ?
N1 C6 C7 C8 179.0(3) . . . . ?
N2 C6 C7 C8 -0.7(6) . . . . ?
C1 N1 C5 C4 -4.0(6) . . . . ?
C1 N1 C5 C11 172.4(3) . . . . ?
C1 N1 C6 N2 102.2(4) . . . . ?
C1 N1 C6 C7 -77.5(5) . . . . ?
C1 C2 C3 C4 -1.7(6) . . . . ?
C2 C3 C4 C5 2.4(6) . . . . ?
C3 C4 C5 N1 0.4(6) . . . . ?
C3 C4 C5 C11 -175.9(4) . . . . ?
C4 C5 C11 C12 -46.3(6) . . . . ?
C4 C5 C11 C13 127.4(4) . . . . ?
C5 N1 C1 O1 -176.3(4) . . . . ?
C5 N1 C1 C2 4.5(5) . . . . ?
C5 N1 C6 N2 -66.0(5) . . . . ?
C5 N1 C6 C7 114.2(4) . . . . ?
C5 C11 C12 C14 174.7(4) . . . . ?
C5 C11 C13 N3 -175.4(4) . . . . ?
C6 N1 C1 O1 15.9(5) . . . . ?
C6 N1 C1 C2 -163.3(3) . . . . ?
C6 N1 C5 C4 163.5(4) . . . . ?
C6 N1 C5 C11 -20.1(5) . . . . ?
C6 N2 C10 C9 0.4(7) . . . . ?
C6 C7 C8 C9 -0.4(6) . . . . ?
C7 C8 C9 C10 1.4(7) . . . . ?
C8 C9 C10 N2 -1.5(8) . . . . ?
C10 N2 C6 N1 -179.0(4) . . . . ?
C10 N2 C6 C7 0.7(6) . . . . ?
C11 C12 C14 C15 0.0(7) . . . . ?
C11 C12 C14 C16 179.9(5) . . . . ?
C12 C11 C13 N3 -1.5(6) . . . . ?
C12 C14 C15 N3 -0.1(8) . . . . ?
C12 C14 C16 F1 -127.3(6) . . . . ?
C12 C14 C16 F2 110.1(7) . . . . ?
C12 C14 C16 F3 -6.7(8) . . . . ?
C13 N3 C15 C14 -0.6(7) . . . . ?
C13 C11 C12 C14 0.7(6) . . . . ?
C15 N3 C13 C11 1.4(7) . . . . ?
C15 C14 C16 F1 52.5(8) . . . . ?
C15 C14 C16 F2 -70.1(7) . . . . ?
C15 C14 C16 F3 173.1(5) . . . . ?
C16 C14 C15 N3 -180.0(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
