# Electronic Supplementary Material (ESI) for ChemComm.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2165940'
loop_
_audit_author_name
_audit_author_address
Tet-shield
;Yunnan University
China
;
_audit_update_record             
;
2022-04-12 deposited with the CCDC.	2022-08-16 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            'C22 H17 F N4 O'
_chemical_formula_weight         372.39

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                   5.5665(3)
_cell_length_b                   23.9215(16)
_cell_length_c                   13.9094(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.355(3)
_cell_angle_gamma                90
_cell_volume                     1851.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3322
_cell_measurement_theta_min      2.2460
_cell_measurement_theta_max      28.0677

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5726
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 CELL 0.71093    5.583   24.026   13.954   89.941   91.334   89.971
;
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  graphite
_diffrn_measurement_method       'CCD area detector'
_diffrn_detector_area_resol_mean 'phi and omega scans'
_diffrn_reflns_number            17537
_diffrn_reflns_av_unetI/netI     0.0926
_diffrn_reflns_av_R_equivalents  0.1214
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.246
_diffrn_reflns_theta_max         25.142
_diffrn_reflns_theta_full        25.142
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3314
_reflns_number_gt                1599
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_publication_material  'SHELXT 2014/5 (Sheldrick, 2014)'
_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)+(0.1275P)²+0.0100P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3314
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1634
_refine_ls_R_factor_gt           0.0777
_refine_ls_wR_factor_ref         0.2642
_refine_ls_wR_factor_gt          0.1981
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 -0.0953(5) 0.51714(13) 0.88239(18) 0.0838(9) Uani 1 1 d . . . . .
O1 O 0.8016(5) 0.77779(15) 0.6258(2) 0.0719(10) Uani 1 1 d . . . . .
C22 C 0.6897(12) 0.8931(3) 0.6412(4) 0.103(2) Uani 1 1 d . . . . .
H22A H 0.566932 0.867357 0.649846 0.124 Uiso 1 1 calc R U . . .
H22B H 0.658815 0.931172 0.646849 0.124 Uiso 1 1 calc R U . . .
N1 N 0.6050(5) 0.64553(16) 0.6017(2) 0.0542(10) Uani 1 1 d . . . . .
N4 N 0.2933(6) 0.67665(18) 0.5145(2) 0.0668(11) Uani 1 1 d . . . . .
N3 N 0.3219(6) 0.71056(18) 0.5879(3) 0.0691(11) Uani 1 1 d . . . . .
C17 C 0.0577(8) 0.5600(2) 0.8636(3) 0.0623(12) Uani 1 1 d . . . . .
C16 C -0.0022(8) 0.5969(2) 0.7927(3) 0.0643(13) Uani 1 1 d . . . . .
H16 H -0.143703 0.592559 0.756596 0.077 Uiso 1 1 calc R U . . .
C15 C 0.1502(7) 0.6408(2) 0.7752(3) 0.0629(13) Uani 1 1 d . . . . .
H15 H 0.110381 0.666276 0.726987 0.076 Uiso 1 1 calc R U . . .
C14 C 0.3622(7) 0.6477(2) 0.8283(3) 0.0553(12) Uani 1 1 d . . . . .
C9 C 0.5286(7) 0.6959(2) 0.8156(3) 0.0585(12) Uani 1 1 d . . . . .
C8 C 0.5942(7) 0.71733(19) 0.7261(3) 0.0547(11) Uani 1 1 d . . . . .
N2 N 0.5071(6) 0.69086(16) 0.6391(2) 0.0559(10) Uani 1 1 d . . . . .
C7 C 0.4668(7) 0.63744(19) 0.5236(3) 0.0523(11) Uani 1 1 d . . . . .
C4 C 0.4970(7) 0.5916(2) 0.4548(3) 0.0540(11) Uani 1 1 d . . . . .
C3 C 0.3199(8) 0.5815(2) 0.3854(3) 0.0672(13) Uani 1 1 d . . . . .
H3 H 0.185190 0.604424 0.381124 0.081 Uiso 1 1 calc R U . . .
C2 C 0.3435(9) 0.5374(2) 0.3229(3) 0.0781(15) Uani 1 1 d . . . . .
H2 H 0.223193 0.530489 0.276867 0.094 Uiso 1 1 calc R U . . .
C1 C 0.5431(10) 0.5032(3) 0.3275(3) 0.0790(15) Uani 1 1 d . . . . .
H1 H 0.557350 0.473227 0.285541 0.095 Uiso 1 1 calc R U . . .
C10 C 0.6323(8) 0.7213(2) 0.8965(3) 0.0684(13) Uani 1 1 d . . . . .
H10 H 0.593258 0.708565 0.957380 0.082 Uiso 1 1 calc R U . . .
C11 C 0.7913(8) 0.7649(2) 0.8882(3) 0.0754(15) Uani 1 1 d . . . . .
H11 H 0.857736 0.781013 0.943531 0.090 Uiso 1 1 calc R U . . .
C12 C 0.8543(8) 0.7852(2) 0.7997(3) 0.0736(14) Uani 1 1 d . . . . .
H12 H 0.963094 0.814573 0.795279 0.088 Uiso 1 1 calc R U . . .
C13 C 0.7532(7) 0.7614(2) 0.7173(3) 0.0616(12) Uani 1 1 d . . . . .
C20 C 0.9825(8) 0.8182(2) 0.6099(4) 0.0742(14) Uani 1 1 d . . . . .
H20A H 1.041139 0.813545 0.545264 0.089 Uiso 1 1 calc R U . . .
H20B H 1.115928 0.811394 0.654448 0.089 Uiso 1 1 calc R U . . .
C21 C 0.9015(10) 0.8762(2) 0.6215(4) 0.0829(15) Uani 1 1 d . . . . .
H21 H 1.017015 0.903770 0.613572 0.100 Uiso 1 1 calc R U . . .
C5 C 0.6962(8) 0.5583(2) 0.4590(3) 0.0667(13) Uani 1 1 d . . . . .
H5 H 0.816481 0.565165 0.504997 0.080 Uiso 1 1 calc R U . . .
C6 C 0.7203(9) 0.5142(2) 0.3951(3) 0.0772(15) Uani 1 1 d . . . . .
H6 H 0.857442 0.492046 0.398047 0.093 Uiso 1 1 calc R U . . .
C19 C 0.4171(8) 0.6077(2) 0.8983(3) 0.0634(13) Uani 1 1 d . . . . .
H19 H 0.560971 0.610740 0.933286 0.076 Uiso 1 1 calc R U . . .
C18 C 0.2658(8) 0.5642(2) 0.9171(3) 0.0660(13) Uani 1 1 d . . . . .
H18 H 0.303479 0.538302 0.964921 0.079 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 C17 1.363(5) . ?
O1 C13 1.365(5) . ?
O1 C20 1.417(5) . ?
C22 C21 1.283(7) . ?
C22 H22A 0.9300 . ?
C22 H22B 0.9300 . ?
N1 N2 1.325(5) . ?
N1 C7 1.331(5) . ?
N4 N3 1.312(5) . ?
N4 C7 1.350(5) . ?
N3 N2 1.326(4) . ?
C17 C16 1.359(6) . ?
C17 C18 1.365(6) . ?
C16 C15 1.374(6) . ?
C16 H16 0.9300 . ?
C15 C14 1.387(5) . ?
C15 H15 0.9300 . ?
C14 C19 1.392(6) . ?
C14 C9 1.492(6) . ?
C9 C10 1.393(6) . ?
C9 C8 1.403(6) . ?
C8 C13 1.383(6) . ?
C8 N2 1.439(5) . ?
C7 C4 1.467(6) . ?
C4 C5 1.366(6) . ?
C4 C3 1.385(5) . ?
C3 C2 1.376(7) . ?
C3 H3 0.9300 . ?
C2 C1 1.380(7) . ?
C2 H2 0.9300 . ?
C1 C6 1.371(7) . ?
C1 H1 0.9300 . ?
C10 C11 1.374(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.389(6) . ?
C12 H12 0.9300 . ?
C20 C21 1.468(7) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21 0.9300 . ?
C5 C6 1.387(7) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C19 C18 1.368(6) . ?
C19 H19 0.9300 . ?
C18 H18 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
C13 O1 C20 119.9(4) . . ?
C21 C22 H22A 120.0 . . ?
C21 C22 H22B 120.0 . . ?
H22A C22 H22B 120.0 . . ?
N2 N1 C7 101.8(3) . . ?
N3 N4 C7 106.5(3) . . ?
N4 N3 N2 106.1(4) . . ?
C16 C17 F1 119.0(4) . . ?
C16 C17 C18 122.5(5) . . ?
F1 C17 C18 118.5(4) . . ?
C17 C16 C15 118.8(4) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C16 C15 C14 121.2(4) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C14 C19 117.4(4) . . ?
C15 C14 C9 123.5(4) . . ?
C19 C14 C9 119.1(4) . . ?
C10 C9 C8 116.5(4) . . ?
C10 C9 C14 119.3(4) . . ?
C8 C9 C14 124.3(4) . . ?
C13 C8 C9 122.6(4) . . ?
C13 C8 N2 117.6(4) . . ?
C9 C8 N2 119.7(4) . . ?
N1 N2 N3 113.7(3) . . ?
N1 N2 C8 123.8(3) . . ?
N3 N2 C8 122.5(4) . . ?
N1 C7 N4 112.0(4) . . ?
N1 C7 C4 124.6(4) . . ?
N4 C7 C4 123.4(4) . . ?
C5 C4 C3 119.4(4) . . ?
C5 C4 C7 120.9(4) . . ?
C3 C4 C7 119.7(4) . . ?
C2 C3 C4 119.9(5) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.1 . . ?
C3 C2 C1 120.9(4) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C6 C1 C2 118.9(5) . . ?
C6 C1 H1 120.5 . . ?
C2 C1 H1 120.5 . . ?
C11 C10 C9 121.2(4) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 121.5(4) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C11 C12 C13 119.1(5) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
O1 C13 C8 116.3(4) . . ?
O1 C13 C12 124.5(4) . . ?
C8 C13 C12 119.2(4) . . ?
O1 C20 C21 114.0(4) . . ?
O1 C20 H20A 108.8 . . ?
C21 C20 H20A 108.8 . . ?
O1 C20 H20B 108.8 . . ?
C21 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
C22 C21 C20 127.5(6) . . ?
C22 C21 H21 116.3 . . ?
C20 C21 H21 116.3 . . ?
C4 C5 C6 120.5(4) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 120.4(5) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C18 C19 C14 122.0(4) . . ?
C18 C19 H19 119.0 . . ?
C14 C19 H19 119.0 . . ?
C17 C18 C19 118.0(5) . . ?
C17 C18 H18 121.0 . . ?
C19 C18 H18 121.0 . . ?

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 N4 N3 N2 -0.7(5) . . . . ?
F1 C17 C16 C15 178.7(4) . . . . ?
C18 C17 C16 C15 -1.3(7) . . . . ?
C17 C16 C15 C14 0.2(7) . . . . ?
C16 C15 C14 C19 1.5(6) . . . . ?
C16 C15 C14 C9 -177.1(4) . . . . ?
C15 C14 C9 C10 138.3(4) . . . . ?
C19 C14 C9 C10 -40.1(6) . . . . ?
C15 C14 C9 C8 -43.1(6) . . . . ?
C19 C14 C9 C8 138.4(4) . . . . ?
C10 C9 C8 C13 0.0(7) . . . . ?
C14 C9 C8 C13 -178.6(4) . . . . ?
C10 C9 C8 N2 175.9(4) . . . . ?
C14 C9 C8 N2 -2.7(6) . . . . ?
C7 N1 N2 N3 -0.7(4) . . . . ?
C7 N1 N2 C8 -179.6(4) . . . . ?
N4 N3 N2 N1 0.9(5) . . . . ?
N4 N3 N2 C8 179.8(4) . . . . ?
C13 C8 N2 N1 94.7(5) . . . . ?
C9 C8 N2 N1 -81.4(5) . . . . ?
C13 C8 N2 N3 -84.1(5) . . . . ?
C9 C8 N2 N3 99.8(5) . . . . ?
N2 N1 C7 N4 0.3(4) . . . . ?
N2 N1 C7 C4 -179.8(4) . . . . ?
N3 N4 C7 N1 0.3(5) . . . . ?
N3 N4 C7 C4 -179.7(4) . . . . ?
N1 C7 C4 C5 -10.1(6) . . . . ?
N4 C7 C4 C5 169.8(4) . . . . ?
N1 C7 C4 C3 169.0(4) . . . . ?
N4 C7 C4 C3 -11.1(6) . . . . ?
C5 C4 C3 C2 1.4(7) . . . . ?
C7 C4 C3 C2 -177.8(4) . . . . ?
C4 C3 C2 C1 -0.7(7) . . . . ?
C3 C2 C1 C6 -0.7(8) . . . . ?
C8 C9 C10 C11 -0.3(7) . . . . ?
C14 C9 C10 C11 178.3(4) . . . . ?
C9 C10 C11 C12 0.1(8) . . . . ?
C10 C11 C12 C13 0.5(8) . . . . ?
C20 O1 C13 C8 -172.9(4) . . . . ?
C20 O1 C13 C12 6.2(7) . . . . ?
C9 C8 C13 O1 179.7(4) . . . . ?
N2 C8 C13 O1 3.8(6) . . . . ?
C9 C8 C13 C12 0.6(7) . . . . ?
N2 C8 C13 C12 -175.4(4) . . . . ?
C11 C12 C13 O1 -179.9(4) . . . . ?
C11 C12 C13 C8 -0.8(7) . . . . ?
C13 O1 C20 C21 -82.7(5) . . . . ?
O1 C20 C21 C22 -2.0(8) . . . . ?
C3 C4 C5 C6 -0.7(7) . . . . ?
C7 C4 C5 C6 178.4(4) . . . . ?
C2 C1 C6 C5 1.4(8) . . . . ?
C4 C5 C6 C1 -0.7(8) . . . . ?
C15 C14 C19 C18 -2.2(6) . . . . ?
C9 C14 C19 C18 176.4(4) . . . . ?
C16 C17 C18 C19 0.5(7) . . . . ?
F1 C17 C18 C19 -179.4(4) . . . . ?
C14 C19 C18 C17 1.2(7) . . . . ?

_refine_diff_density_max         0.209
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.054



