# Electronic Supplementary Material (ESI) for ChemComm.
# 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_cu_d8v22266_0m
_database_code_depnum_ccdc_archive 'CCDC 2219238'
loop_
_audit_author_name
_audit_author_address
'Wengang Guo'
;Changzhou Universityi
China
;
_audit_update_record             
;
2022-11-12 deposited with the CCDC.	2022-12-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H20 F N O2'
_chemical_formula_weight         385.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   10.7905(3)
_cell_length_b                   6.0625(2)
_cell_length_c                   15.4957(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.9640(10)
_cell_angle_gamma                90
_cell_volume                     964.27(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9930
_cell_measurement_theta_min      8.615
_cell_measurement_theta_max      140.158

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.734
_shelx_estimated_absorpt_T_min   0.867
_shelx_estimated_absorpt_T_max   0.917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4911
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            15778
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.307
_diffrn_reflns_theta_max         67.953
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.956
_reflns_number_total             3354
_reflns_number_gt                3300
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.798
_reflns_Friedel_fraction_max     0.945
_reflns_Friedel_fraction_full    0.947

_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-2013 (Sheldrick, 2013)'
_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)+(0.0523P)²+0.0831P] 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
_refine_ls_extinction_coef       0.031(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1447 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.04(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3354
_refine_ls_number_parameters     264
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0873
_refine_ls_wR_factor_gt          0.0867
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 1.05167(16) 0.2256(4) 0.95971(10) 0.0881(6) Uani 1 1 d . . . . .
O1 O 0.57156(17) 0.1732(3) 0.55498(11) 0.0642(5) Uani 1 1 d . . . . .
O2 O 0.28512(17) 0.6732(4) 0.94558(12) 0.0721(6) Uani 1 1 d . . . . .
N1 N 0.49267(16) 0.3825(4) 0.67836(13) 0.0560(5) Uani 1 1 d . . . . .
H1 H 0.4448 0.2903 0.6402 0.067 Uiso 1 1 calc R U . . .
C1 C 0.72873(18) 0.3419(3) 0.45851(13) 0.0407(4) Uani 1 1 d . . . . .
H1A H 0.6916 0.2032 0.4432 0.049 Uiso 1 1 calc R U . . .
C2 C 0.80827(17) 0.4301(3) 0.40931(12) 0.0397(4) Uani 1 1 d . . . . .
C3 C 0.8336(2) 0.3150(4) 0.33749(14) 0.0482(5) Uani 1 1 d . . . . .
H3 H 0.7971 0.1764 0.3210 0.058 Uiso 1 1 calc R U . . .
C4 C 0.9113(2) 0.4048(4) 0.29187(15) 0.0552(6) Uani 1 1 d . . . . .
H4 H 0.9260 0.3281 0.2440 0.066 Uiso 1 1 calc R U . . .
C5 C 0.9690(2) 0.6129(4) 0.31683(15) 0.0536(5) Uani 1 1 d . . . . .
H5 H 1.0233 0.6711 0.2862 0.064 Uiso 1 1 calc R U . . .
C6 C 0.94632(19) 0.7290(4) 0.38509(14) 0.0480(5) Uani 1 1 d . . . . .
H6 H 0.9847 0.8668 0.4005 0.058 Uiso 1 1 calc R U . . .
C7 C 0.86451(18) 0.6428(3) 0.43332(12) 0.0406(4) Uani 1 1 d . . . . .
C8 C 0.83586(19) 0.7603(3) 0.50331(13) 0.0447(5) Uani 1 1 d . . . . .
H8 H 0.8704 0.9008 0.5184 0.054 Uiso 1 1 calc R U . . .
C9 C 0.75860(19) 0.6720(3) 0.54913(13) 0.0448(5) Uani 1 1 d . . . . .
H9 H 0.7404 0.7535 0.5946 0.054 Uiso 1 1 calc R U . . .
C10 C 0.70531(17) 0.4569(3) 0.52848(13) 0.0404(4) Uani 1 1 d . . . . .
C11 C 0.62422(18) 0.3495(4) 0.57878(14) 0.0448(5) Uani 1 1 d . . . . .
C12 C 0.61276(18) 0.4568(4) 0.66576(14) 0.0450(5) Uani 1 1 d . . . . .
H12 H 0.6094 0.6174 0.6581 0.054 Uiso 1 1 calc R U . . .
C13 C 0.73333(18) 0.3963(3) 0.74489(13) 0.0428(5) Uani 1 1 d . . . . .
C14 C 0.8353(2) 0.5430(4) 0.77935(15) 0.0495(5) Uani 1 1 d . . . . .
H14 H 0.8315 0.6820 0.7533 0.059 Uiso 1 1 calc R U . . .
C15 C 0.9430(2) 0.4865(5) 0.85195(15) 0.0569(6) Uani 1 1 d . . . . .
H15 H 1.0108 0.5859 0.8749 0.068 Uiso 1 1 calc R U . . .
C16 C 0.9468(2) 0.2819(5) 0.88875(15) 0.0577(6) Uani 1 1 d . . . . .
C17 C 0.8488(3) 0.1318(4) 0.85752(17) 0.0645(6) Uani 1 1 d . . . . .
H17 H 0.8536 -0.0064 0.8844 0.077 Uiso 1 1 calc R U . . .
C18 C 0.7421(2) 0.1901(4) 0.78494(15) 0.0565(6) Uani 1 1 d . . . . .
H18 H 0.6750 0.0890 0.7626 0.068 Uiso 1 1 calc R U . . .
C19 C 0.45161(18) 0.4554(4) 0.75046(13) 0.0434(5) Uani 1 1 d . . . . .
C20 C 0.4932(2) 0.6517(4) 0.79610(16) 0.0515(5) Uani 1 1 d . . . . .
H20 H 0.5571 0.7339 0.7820 0.062 Uiso 1 1 calc R U . . .
C21 C 0.4418(2) 0.7289(4) 0.86224(15) 0.0515(5) Uani 1 1 d . . . . .
H21 H 0.4714 0.8610 0.8920 0.062 Uiso 1 1 calc R U . . .
C22 C 0.3469(2) 0.6091(4) 0.88368(14) 0.0498(5) Uani 1 1 d . . . . .
C23 C 0.3073(2) 0.4097(4) 0.84099(14) 0.0500(5) Uani 1 1 d . . . . .
H23 H 0.2448 0.3266 0.8564 0.060 Uiso 1 1 calc R U . . .
C24 C 0.35915(19) 0.3322(4) 0.77602(14) 0.0459(5) Uani 1 1 d . . . . .
H24 H 0.3324 0.1963 0.7488 0.055 Uiso 1 1 calc R U . . .
C25 C 0.3285(3) 0.8686(5) 0.9951(2) 0.0746(8) Uani 1 1 d . . . . .
H25A H 0.3217 0.9894 0.9538 0.112 Uiso 1 1 calc R U . . .
H25B H 0.4177 0.8514 1.0317 0.112 Uiso 1 1 calc R U . . .
H25C H 0.2757 0.8981 1.0336 0.112 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 C16 1.356(3) . ?
O1 C11 1.213(3) . ?
O2 C22 1.382(3) . ?
O2 C25 1.411(3) . ?
N1 C19 1.395(3) . ?
N1 C12 1.441(2) . ?
N1 H1 0.8600 . ?
C1 C10 1.376(3) . ?
C1 C2 1.417(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.410(3) . ?
C2 C7 1.425(3) . ?
C3 C4 1.365(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.407(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.355(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.421(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.409(3) . ?
C8 C9 1.361(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.421(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.489(3) . ?
C11 C12 1.535(3) . ?
C12 C13 1.532(3) . ?
C12 H12 0.9800 . ?
C13 C18 1.385(3) . ?
C13 C14 1.388(3) . ?
C14 C15 1.388(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.360(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.365(4) . ?
C17 C18 1.385(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.387(3) . ?
C19 C24 1.398(3) . ?
C20 C21 1.388(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.377(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.381(3) . ?
C23 C24 1.376(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
C22 O2 C25 117.60(19) . . ?
C19 N1 C12 122.05(17) . . ?
C19 N1 H1 119.0 . . ?
C12 N1 H1 119.0 . . ?
C10 C1 C2 121.43(17) . . ?
C10 C1 H1A 119.3 . . ?
C2 C1 H1A 119.3 . . ?
C3 C2 C1 122.34(18) . . ?
C3 C2 C7 118.90(18) . . ?
C1 C2 C7 118.75(17) . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.6(2) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 120.7(2) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 122.55(19) . . ?
C8 C7 C2 118.80(17) . . ?
C6 C7 C2 118.65(18) . . ?
C9 C8 C7 121.17(18) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 120.94(18) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C1 C10 C9 118.83(18) . . ?
C1 C10 C11 118.12(17) . . ?
C9 C10 C11 123.05(17) . . ?
O1 C11 C10 121.44(18) . . ?
O1 C11 C12 118.88(19) . . ?
C10 C11 C12 119.58(17) . . ?
N1 C12 C13 113.20(17) . . ?
N1 C12 C11 107.80(16) . . ?
C13 C12 C11 108.83(16) . . ?
N1 C12 H12 109.0 . . ?
C13 C12 H12 109.0 . . ?
C11 C12 H12 109.0 . . ?
C18 C13 C14 118.0(2) . . ?
C18 C13 C12 119.88(18) . . ?
C14 C13 C12 122.12(19) . . ?
C15 C14 C13 121.3(2) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C16 C15 C14 118.3(2) . . ?
C16 C15 H15 120.8 . . ?
C14 C15 H15 120.8 . . ?
F1 C16 C15 118.6(2) . . ?
F1 C16 C17 118.8(2) . . ?
C15 C16 C17 122.6(2) . . ?
C16 C17 C18 118.5(2) . . ?
C16 C17 H17 120.8 . . ?
C18 C17 H17 120.8 . . ?
C17 C18 C13 121.3(2) . . ?
C17 C18 H18 119.4 . . ?
C13 C18 H18 119.4 . . ?
C20 C19 N1 123.22(19) . . ?
C20 C19 C24 117.46(19) . . ?
N1 C19 C24 119.24(19) . . ?
C19 C20 C21 121.73(19) . . ?
C19 C20 H20 119.1 . . ?
C21 C20 H20 119.1 . . ?
C22 C21 C20 119.8(2) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C21 C22 O2 125.0(2) . . ?
C21 C22 C23 119.30(19) . . ?
O2 C22 C23 115.72(19) . . ?
C24 C23 C22 120.90(18) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C23 C24 C19 120.76(19) . . ?
C23 C24 H24 119.6 . . ?
C19 C24 H24 119.6 . . ?
O2 C25 H25A 109.5 . . ?
O2 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O2 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
C10 C1 C2 C3 179.92(17) . . . . ?
C10 C1 C2 C7 -0.1(3) . . . . ?
C1 C2 C3 C4 -179.70(18) . . . . ?
C7 C2 C3 C4 0.3(3) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C3 C4 C5 C6 -1.4(3) . . . . ?
C4 C5 C6 C7 0.5(3) . . . . ?
C5 C6 C7 C8 -178.47(18) . . . . ?
C5 C6 C7 C2 0.9(3) . . . . ?
C3 C2 C7 C8 178.11(17) . . . . ?
C1 C2 C7 C8 -1.9(2) . . . . ?
C3 C2 C7 C6 -1.3(3) . . . . ?
C1 C2 C7 C6 178.76(16) . . . . ?
C6 C7 C8 C9 -179.06(18) . . . . ?
C2 C7 C8 C9 1.6(3) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
C2 C1 C10 C9 2.3(3) . . . . ?
C2 C1 C10 C11 -178.02(16) . . . . ?
C8 C9 C10 C1 -2.6(3) . . . . ?
C8 C9 C10 C11 177.72(18) . . . . ?
C1 C10 C11 O1 -5.6(3) . . . . ?
C9 C10 C11 O1 174.0(2) . . . . ?
C1 C10 C11 C12 170.92(17) . . . . ?
C9 C10 C11 C12 -9.4(3) . . . . ?
C19 N1 C12 C13 61.4(3) . . . . ?
C19 N1 C12 C11 -178.2(2) . . . . ?
O1 C11 C12 N1 -27.7(3) . . . . ?
C10 C11 C12 N1 155.73(18) . . . . ?
O1 C11 C12 C13 95.5(2) . . . . ?
C10 C11 C12 C13 -81.1(2) . . . . ?
N1 C12 C13 C18 41.3(3) . . . . ?
C11 C12 C13 C18 -78.6(2) . . . . ?
N1 C12 C13 C14 -138.0(2) . . . . ?
C11 C12 C13 C14 102.1(2) . . . . ?
C18 C13 C14 C15 -0.2(3) . . . . ?
C12 C13 C14 C15 179.04(19) . . . . ?
C13 C14 C15 C16 0.3(3) . . . . ?
C14 C15 C16 F1 180.0(2) . . . . ?
C14 C15 C16 C17 -0.5(4) . . . . ?
F1 C16 C17 C18 -179.9(2) . . . . ?
C15 C16 C17 C18 0.6(4) . . . . ?
C16 C17 C18 C13 -0.6(4) . . . . ?
C14 C13 C18 C17 0.4(3) . . . . ?
C12 C13 C18 C17 -178.9(2) . . . . ?
C12 N1 C19 C20 22.9(3) . . . . ?
C12 N1 C19 C24 -160.4(2) . . . . ?
N1 C19 C20 C21 174.2(2) . . . . ?
C24 C19 C20 C21 -2.5(3) . . . . ?
C19 C20 C21 C22 -0.1(3) . . . . ?
C20 C21 C22 O2 -177.4(2) . . . . ?
C20 C21 C22 C23 2.1(3) . . . . ?
C25 O2 C22 C21 -4.5(4) . . . . ?
C25 O2 C22 C23 175.9(2) . . . . ?
C21 C22 C23 C24 -1.5(3) . . . . ?
O2 C22 C23 C24 178.0(2) . . . . ?
C22 C23 C24 C19 -1.1(3) . . . . ?
C20 C19 C24 C23 3.1(3) . . . . ?
N1 C19 C24 C23 -173.79(19) . . . . ?

_refine_diff_density_max         0.146
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.023

_shelxl_version_number           2013-4



