# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2024

####################################################################### 
# 
# 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 2300843'
loop_
_audit_author_name
_audit_author_address
li
;nwnu
China
;
_audit_update_record             
;
2023-10-12 deposited with the CCDC.	2024-06-26 downloaded from the CCDC.
;
_audit_creation_date             2023-09-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H12 F N3'
_chemical_formula_sum            'C20 H12 F N3'
_chemical_formula_weight         313.33
_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'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   27.7164(13)
_cell_length_b                   7.2580(3)
_cell_length_c                   17.6388(7)
_cell_angle_alpha                90
_cell_angle_beta                 118.0230(10)
_cell_angle_gamma                90
_cell_volume                     3132.3(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7649
_cell_measurement_temperature    298.06
_cell_measurement_theta_max      24.05
_cell_measurement_theta_min      2.93
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0563 before and 0.0476 after correction.
The Ratio of minimum to maximum transmission is 0.9528.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            31494
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.291
_diffrn_reflns_theta_min         3.122
_diffrn_ambient_temperature      298.06
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2411
_reflns_number_total             3890
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3890
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0459
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0458P)²+1.0127P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1171
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C10(H10), C14(H14), C16(H16), C18(H18), C20(H20), C21(H21), C15(H15),
 C2(H2), C17(H17), C9(H9), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
F F 0.52428(5) 0.01341(13) 0.68828(7) 0.0929(4) Uani 1 1 d . . . . .
N1 N 0.44621(5) 0.32876(16) 0.54291(7) 0.0504(3) Uani 1 1 d . . . . .
N3 N 0.45708(6) 0.15022(17) 0.57070(8) 0.0630(4) Uani 1 1 d . . . . .
C4 C 0.36403(6) 0.2393(2) 0.40963(9) 0.0505(4) Uani 1 1 d . . . . .
C6 C 0.48073(7) 0.6367(2) 0.57495(10) 0.0542(4) Uani 1 1 d . . . . .
H6 H 0.506807 0.721746 0.609859 0.065 Uiso 1 1 calc R U . . .
C8 C 0.48586(6) 0.44986(19) 0.59899(9) 0.0483(3) Uani 1 1 d . . . . .
C10 C 0.57741(6) 0.5672(2) 0.78507(9) 0.0538(4) Uani 1 1 d . . . . .
H10 H 0.549094 0.652079 0.760151 0.065 Uiso 1 1 calc R U . . .
C12 C 0.40231(6) 0.3810(2) 0.46647(9) 0.0496(4) Uani 1 1 d . . . . .
C14 C 0.34995(6) 0.2448(2) 0.32317(9) 0.0588(4) Uani 1 1 d . . . . .
H14 H 0.365228 0.334466 0.303305 0.071 Uiso 1 1 calc R U . . .
C16 C 0.62322(6) 0.6114(2) 0.86082(9) 0.0565(4) Uani 1 1 d . . . . .
H16 H 0.625589 0.725429 0.886381 0.068 Uiso 1 1 calc R U . . .
C18 C 0.34051(7) 0.1054(2) 0.43789(11) 0.0630(4) Uani 1 1 d . . . . .
H18 H 0.349422 0.099235 0.495663 0.076 Uiso 1 1 calc R U . . .
C20 C 0.43758(7) 0.6917(2) 0.50068(10) 0.0593(4) Uani 1 1 d . . . . .
H20 H 0.433942 0.815303 0.485062 0.071 Uiso 1 1 calc R U . . .
C21 C 0.39822(7) 0.5640(2) 0.44695(10) 0.0564(4) Uani 1 1 d . . . . .
H21 H 0.368607 0.605370 0.396765 0.068 Uiso 1 1 calc R U . . .
C11 C 0.52357(6) 0.3432(2) 0.66693(9) 0.0529(4) Uani 1 1 d . . . . .
C3 C 0.66545(7) 0.4867(2) 0.89861(9) 0.0587(4) Uani 1 1 d . . . . .
N2 N 0.74913(8) 0.5498(3) 1.04479(10) 0.0999(6) Uani 1 1 d . . . . .
C13 C 0.57288(6) 0.3971(2) 0.74523(9) 0.0515(4) Uani 1 1 d . . . . .
C7 C 0.50254(7) 0.1676(2) 0.64282(10) 0.0622(4) Uani 1 1 d . . . . .
C15 C 0.29073(7) -0.0120(3) 0.29476(13) 0.0749(5) Uani 1 1 d . . . . .
H15 H 0.266259 -0.096714 0.256411 0.090 Uiso 1 1 calc R U . . .
C2 C 0.31357(7) 0.1193(3) 0.26601(11) 0.0697(5) Uani 1 1 d . . . . .
H2 H 0.304664 0.124041 0.208213 0.084 Uiso 1 1 calc R U . . .
C17 C 0.66220(8) 0.3189(3) 0.85875(11) 0.0722(5) Uani 1 1 d . . . . .
H17 H 0.690917 0.235351 0.883222 0.087 Uiso 1 1 calc R U . . .
C9 C 0.30376(7) -0.0192(3) 0.38012(13) 0.0746(5) Uani 1 1 d . . . . .
H9 H 0.287822 -0.108253 0.399173 0.090 Uiso 1 1 calc R U . . .
C19 C 0.71217(8) 0.5246(3) 0.98004(11) 0.0725(5) Uani 1 1 d . . . . .
C5 C 0.61658(7) 0.2760(2) 0.78311(11) 0.0692(5) Uani 1 1 d . . . . .
H5 H 0.614972 0.163516 0.756799 0.083 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
F C7 1.3432(17) . ?
N1 N3 1.3680(17) . ?
N1 C8 1.3919(17) . ?
N1 C12 1.3786(18) . ?
N3 C7 1.310(2) . ?
C4 C12 1.4794(19) . ?
C4 C14 1.386(2) . ?
C4 C18 1.387(2) . ?
C6 H6 0.9300 . ?
C6 C8 1.408(2) . ?
C6 C20 1.354(2) . ?
C8 C11 1.397(2) . ?
C10 H10 0.9300 . ?
C10 C16 1.381(2) . ?
C10 C13 1.397(2) . ?
C12 C21 1.363(2) . ?
C14 H14 0.9300 . ?
C14 C2 1.381(2) . ?
C16 H16 0.9300 . ?
C16 C3 1.379(2) . ?
C18 H18 0.9300 . ?
C18 C9 1.385(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.406(2) . ?
C21 H21 0.9300 . ?
C11 C13 1.468(2) . ?
C11 C7 1.383(2) . ?
C3 C17 1.388(2) . ?
C3 C19 1.438(2) . ?
N2 C19 1.135(2) . ?
C13 C5 1.388(2) . ?
C15 H15 0.9300 . ?
C15 C2 1.366(3) . ?
C15 C9 1.374(3) . ?
C2 H2 0.9300 . ?
C17 H17 0.9300 . ?
C17 C5 1.375(2) . ?
C9 H9 0.9300 . ?
C5 H5 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
N3 N1 C8 112.09(12) . . ?
N3 N1 C12 123.75(12) . . ?
C12 N1 C8 124.11(12) . . ?
C7 N3 N1 101.90(12) . . ?
C14 C4 C12 117.86(14) . . ?
C14 C4 C18 118.60(14) . . ?
C18 C4 C12 123.51(14) . . ?
C8 C6 H6 120.2 . . ?
C20 C6 H6 120.2 . . ?
C20 C6 C8 119.60(14) . . ?
N1 C8 C6 117.37(13) . . ?
N1 C8 C11 106.40(12) . . ?
C11 C8 C6 136.17(14) . . ?
C16 C10 H10 119.4 . . ?
C16 C10 C13 121.13(15) . . ?
C13 C10 H10 119.4 . . ?
N1 C12 C4 119.61(13) . . ?
C21 C12 N1 116.45(13) . . ?
C21 C12 C4 123.90(14) . . ?
C4 C14 H14 119.5 . . ?
C2 C14 C4 121.06(16) . . ?
C2 C14 H14 119.5 . . ?
C10 C16 H16 120.0 . . ?
C3 C16 C10 120.07(15) . . ?
C3 C16 H16 120.0 . . ?
C4 C18 H18 120.0 . . ?
C9 C18 C4 120.04(16) . . ?
C9 C18 H18 120.0 . . ?
C6 C20 H20 119.7 . . ?
C6 C20 C21 120.70(14) . . ?
C21 C20 H20 119.7 . . ?
C12 C21 C20 121.74(15) . . ?
C12 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
C8 C11 C13 130.53(14) . . ?
C7 C11 C8 102.11(13) . . ?
C7 C11 C13 127.36(14) . . ?
C16 C3 C17 119.53(15) . . ?
C16 C3 C19 121.26(15) . . ?
C17 C3 C19 119.19(16) . . ?
C10 C13 C11 122.22(14) . . ?
C5 C13 C10 117.75(14) . . ?
C5 C13 C11 120.02(14) . . ?
F C7 C11 125.33(14) . . ?
N3 C7 F 117.17(13) . . ?
N3 C7 C11 117.49(14) . . ?
C2 C15 H15 119.9 . . ?
C2 C15 C9 120.29(17) . . ?
C9 C15 H15 119.9 . . ?
C14 C2 H2 120.1 . . ?
C15 C2 C14 119.70(16) . . ?
C15 C2 H2 120.1 . . ?
C3 C17 H17 120.0 . . ?
C5 C17 C3 120.10(16) . . ?
C5 C17 H17 120.0 . . ?
C18 C9 H9 119.8 . . ?
C15 C9 C18 120.31(18) . . ?
C15 C9 H9 119.8 . . ?
N2 C19 C3 178.2(2) . . ?
C13 C5 H5 119.3 . . ?
C17 C5 C13 121.38(15) . . ?
C17 C5 H5 119.3 . . ?

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
N1 N3 C7 F 178.86(15) . . . . ?
N1 N3 C7 C11 0.3(2) . . . . ?
N1 C8 C11 C13 -178.32(15) . . . . ?
N1 C8 C11 C7 1.05(16) . . . . ?
N1 C12 C21 C20 1.9(2) . . . . ?
N3 N1 C8 C6 176.64(13) . . . . ?
N3 N1 C8 C11 -1.03(17) . . . . ?
N3 N1 C12 C4 -0.1(2) . . . . ?
N3 N1 C12 C21 -178.04(14) . . . . ?
C4 C12 C21 C20 -175.97(14) . . . . ?
C4 C14 C2 C15 0.4(3) . . . . ?
C4 C18 C9 C15 0.5(3) . . . . ?
C6 C8 C11 C13 4.7(3) . . . . ?
C6 C8 C11 C7 -175.95(18) . . . . ?
C6 C20 C21 C12 -1.1(2) . . . . ?
C8 N1 N3 C7 0.49(18) . . . . ?
C8 N1 C12 C4 177.00(13) . . . . ?
C8 N1 C12 C21 -0.9(2) . . . . ?
C8 C6 C20 C21 -0.7(2) . . . . ?
C8 C11 C13 C10 31.1(2) . . . . ?
C8 C11 C13 C5 -150.22(17) . . . . ?
C8 C11 C7 F -179.34(17) . . . . ?
C8 C11 C7 N3 -0.9(2) . . . . ?
C10 C16 C3 C17 1.8(2) . . . . ?
C10 C16 C3 C19 -176.27(15) . . . . ?
C10 C13 C5 C17 2.0(3) . . . . ?
C12 N1 N3 C7 177.91(14) . . . . ?
C12 N1 C8 C6 -0.8(2) . . . . ?
C12 N1 C8 C11 -178.44(13) . . . . ?
C12 C4 C14 C2 -178.68(15) . . . . ?
C12 C4 C18 C9 178.09(15) . . . . ?
C14 C4 C12 N1 -132.19(15) . . . . ?
C14 C4 C12 C21 45.6(2) . . . . ?
C14 C4 C18 C9 0.0(2) . . . . ?
C16 C10 C13 C11 177.03(14) . . . . ?
C16 C10 C13 C5 -1.7(2) . . . . ?
C16 C3 C17 C5 -1.5(3) . . . . ?
C18 C4 C12 N1 49.7(2) . . . . ?
C18 C4 C12 C21 -132.58(17) . . . . ?
C18 C4 C14 C2 -0.4(2) . . . . ?
C20 C6 C8 N1 1.6(2) . . . . ?
C20 C6 C8 C11 178.34(17) . . . . ?
C11 C13 C5 C17 -176.75(16) . . . . ?
C3 C17 C5 C13 -0.4(3) . . . . ?
C13 C10 C16 C3 -0.2(2) . . . . ?
C13 C11 C7 F 0.1(3) . . . . ?
C13 C11 C7 N3 178.54(15) . . . . ?
C7 C11 C13 C10 -148.13(17) . . . . ?
C7 C11 C13 C5 30.6(3) . . . . ?
C2 C15 C9 C18 -0.6(3) . . . . ?
C9 C15 C2 C14 0.1(3) . . . . ?
C19 C3 C17 C5 176.60(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
