# 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_H311_0m
_database_code_depnum_ccdc_archive 'CCDC 2296454'
loop_
_audit_author_name
_audit_author_address
'Qinghe Gao'
;Xinxiang Medical University
China
;
_audit_update_record             
;
2023-09-21 deposited with the CCDC.	2023-10-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H12 F3 N3'
_chemical_formula_weight         363.34

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'
F F 0.0171 0.0103 '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                   9.105(4)
_cell_length_b                   9.483(4)
_cell_length_c                   10.167(4)
_cell_angle_alpha                97.386(6)
_cell_angle_beta                 107.310(6)
_cell_angle_gamma                93.704(6)
_cell_volume                     826.2(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    979
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      23.06

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_F_000             372
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.112
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   ?
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5161
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.124
_diffrn_reflns_theta_max         27.488
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             3685
_reflns_number_gt                2180
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1000P)²] 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         3685
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1035
_refine_ls_R_factor_gt           0.0612
_refine_ls_wR_factor_ref         0.2055
_refine_ls_wR_factor_gt          0.1736
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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 0.7103(3) 1.1780(2) 0.0743(2) 0.1073(8) Uani 1 1 d . . . . .
F2 F 0.9289(3) 1.1011(2) 0.1142(3) 0.1299(10) Uani 1 1 d . . . . .
F3 F 0.7625(3) 1.0423(2) -0.0824(2) 0.1079(8) Uani 1 1 d . . . . .
N1 N 0.6940(2) 0.5015(2) 0.3191(2) 0.0499(5) Uani 1 1 d . . . . .
N2 N 0.5140(2) 0.3433(2) 0.3767(2) 0.0450(5) Uani 1 1 d . . . . .
N3 N 0.5049(2) 0.2292(2) 0.4428(2) 0.0510(6) Uani 1 1 d . . . . .
C1 C 0.2949(3) 0.6004(3) 0.1836(3) 0.0535(7) Uani 1 1 d . . . . .
H1 H 0.312200 0.678510 0.141352 0.064 Uiso 1 1 calc R U . . .
C2 C 0.1465(3) 0.5549(3) 0.1782(3) 0.0607(7) Uani 1 1 d . . . . .
H2 H 0.064489 0.602306 0.132776 0.073 Uiso 1 1 calc R U . . .
C3 C 0.1188(3) 0.4385(3) 0.2403(3) 0.0606(7) Uani 1 1 d . . . . .
H3 H 0.018096 0.409368 0.236980 0.073 Uiso 1 1 calc R U . . .
C4 C 0.2378(3) 0.3650(3) 0.3071(3) 0.0566(7) Uani 1 1 d . . . . .
H4 H 0.218536 0.286226 0.347652 0.068 Uiso 1 1 calc R U . . .
C5 C 0.3881(3) 0.4122(2) 0.3119(2) 0.0447(6) Uani 1 1 d . . . . .
C6 C 0.4208(3) 0.5311(2) 0.2518(2) 0.0459(6) Uani 1 1 d . . . . .
C7 C 0.5812(3) 0.5721(3) 0.2598(3) 0.0465(6) Uani 1 1 d . . . . .
C8 C 0.6226(3) 0.6983(3) 0.2006(2) 0.0462(6) Uani 1 1 d . . . . .
C9 C 0.5913(3) 0.8334(3) 0.2450(3) 0.0561(7) Uani 1 1 d . . . . .
H9 H 0.535560 0.845186 0.308195 0.067 Uiso 1 1 calc R U . . .
C10 C 0.6419(3) 0.9519(3) 0.1967(3) 0.0603(7) Uani 1 1 d . . . . .
H10 H 0.621408 1.042619 0.228676 0.072 Uiso 1 1 calc R U . . .
C11 C 0.7219(3) 0.9357(3) 0.1019(3) 0.0533(7) Uani 1 1 d . . . . .
C12 C 0.7547(4) 0.8002(3) 0.0564(3) 0.0680(8) Uani 1 1 d . . . . .
H12 H 0.809958 0.788592 -0.007075 0.082 Uiso 1 1 calc R U . . .
C13 C 0.7050(3) 0.6829(3) 0.1056(3) 0.0607(7) Uani 1 1 d . . . . .
H13 H 0.727052 0.592446 0.074799 0.073 Uiso 1 1 calc R U . . .
C14 C 0.7805(4) 1.0616(4) 0.0519(4) 0.0723(9) Uani 1 1 d . . . . .
C15 C 0.6625(3) 0.3886(2) 0.3791(2) 0.0459(6) Uani 1 1 d . . . . .
C16 C 0.7578(3) 0.2979(2) 0.4538(2) 0.0461(6) Uani 1 1 d . . . . .
C17 C 0.6567(3) 0.2026(2) 0.4905(2) 0.0477(6) Uani 1 1 d . . . . .
C18 C 0.7155(3) 0.0943(3) 0.5687(3) 0.0558(7) Uani 1 1 d . . . . .
H18 H 0.649754 0.030486 0.593036 0.067 Uiso 1 1 calc R U . . .
C19 C 0.8676(3) 0.0861(3) 0.6066(3) 0.0627(8) Uani 1 1 d . . . . .
H19 H 0.907397 0.014964 0.657595 0.075 Uiso 1 1 calc R U . . .
C20 C 0.9714(3) 0.1828(3) 0.5716(3) 0.0651(8) Uani 1 1 d . . . . .
H20 H 1.076848 0.173845 0.600722 0.078 Uiso 1 1 calc R U . . .
C21 C 0.9187(3) 0.2875(3) 0.4965(3) 0.0591(7) Uani 1 1 d . . . . .
H21 H 0.986492 0.350626 0.473717 0.071 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 C14 1.339(4) . ?
F2 C14 1.315(4) . ?
F3 C14 1.313(4) . ?
N1 C7 1.300(3) . ?
N1 C15 1.354(3) . ?
N2 N3 1.355(3) . ?
N2 C15 1.384(3) . ?
N2 C5 1.391(3) . ?
N3 C17 1.374(3) . ?
C1 C2 1.375(4) . ?
C1 C6 1.403(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.385(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.396(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.405(3) . ?
C6 C7 1.462(3) . ?
C7 C8 1.483(3) . ?
C8 C9 1.379(4) . ?
C8 C13 1.387(4) . ?
C9 C10 1.389(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.370(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.390(4) . ?
C11 C14 1.485(4) . ?
C12 C13 1.380(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C15 C16 1.394(3) . ?
C16 C17 1.409(3) . ?
C16 C21 1.413(4) . ?
C17 C18 1.415(4) . ?
C18 C19 1.333(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.425(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.356(4) . ?
C20 H20 0.9300 . ?
C21 H21 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
C7 N1 C15 118.9(2) . . ?
N3 N2 C15 114.2(2) . . ?
N3 N2 C5 124.5(2) . . ?
C15 N2 C5 121.4(2) . . ?
N2 N3 C17 102.52(19) . . ?
C2 C1 C6 121.1(3) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C1 C2 C3 120.1(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 121.2(3) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 118.1(3) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
N2 C5 C4 121.5(2) . . ?
N2 C5 C6 116.3(2) . . ?
C4 C5 C6 122.2(2) . . ?
C1 C6 C5 117.1(2) . . ?
C1 C6 C7 124.1(2) . . ?
C5 C6 C7 118.7(2) . . ?
N1 C7 C6 122.3(2) . . ?
N1 C7 C8 116.8(2) . . ?
C6 C7 C8 121.0(2) . . ?
C9 C8 C13 118.7(2) . . ?
C9 C8 C7 121.6(2) . . ?
C13 C8 C7 119.5(2) . . ?
C8 C9 C10 120.8(2) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 119.6(2) . . ?
C10 C11 C14 120.9(3) . . ?
C12 C11 C14 119.4(3) . . ?
C13 C12 C11 119.9(3) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C8 120.8(3) . . ?
C12 C13 H13 119.6 . . ?
C8 C13 H13 119.6 . . ?
F3 C14 F2 105.9(3) . . ?
F3 C14 F1 105.0(3) . . ?
F2 C14 F1 105.1(3) . . ?
F3 C14 C11 114.2(3) . . ?
F2 C14 C11 112.9(3) . . ?
F1 C14 C11 113.0(3) . . ?
N1 C15 N2 122.5(2) . . ?
N1 C15 C16 131.9(2) . . ?
N2 C15 C16 105.7(2) . . ?
C15 C16 C17 104.8(2) . . ?
C15 C16 C21 134.8(2) . . ?
C17 C16 C21 120.4(2) . . ?
N3 C17 C16 112.8(2) . . ?
N3 C17 C18 127.0(2) . . ?
C16 C17 C18 120.2(2) . . ?
C19 C18 C17 118.2(3) . . ?
C19 C18 H18 120.9 . . ?
C17 C18 H18 120.9 . . ?
C18 C19 C20 122.2(3) . . ?
C18 C19 H19 118.9 . . ?
C20 C19 H19 118.9 . . ?
C21 C20 C19 121.1(3) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C20 C21 C16 117.9(3) . . ?
C20 C21 H21 121.0 . . ?
C16 C21 H21 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
C15 N2 N3 C17 0.7(2) . . . . ?
C5 N2 N3 C17 -178.9(2) . . . . ?
C6 C1 C2 C3 -0.2(4) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
C2 C3 C4 C5 0.8(4) . . . . ?
N3 N2 C5 C4 -1.7(4) . . . . ?
C15 N2 C5 C4 178.7(2) . . . . ?
N3 N2 C5 C6 178.45(19) . . . . ?
C15 N2 C5 C6 -1.1(3) . . . . ?
C3 C4 C5 N2 -179.7(2) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C2 C1 C6 C5 1.0(4) . . . . ?
C2 C1 C6 C7 179.0(2) . . . . ?
N2 C5 C6 C1 178.8(2) . . . . ?
C4 C5 C6 C1 -1.0(4) . . . . ?
N2 C5 C6 C7 0.7(3) . . . . ?
C4 C5 C6 C7 -179.1(2) . . . . ?
C15 N1 C7 C6 -2.0(4) . . . . ?
C15 N1 C7 C8 177.6(2) . . . . ?
C1 C6 C7 N1 -177.1(2) . . . . ?
C5 C6 C7 N1 0.8(4) . . . . ?
C1 C6 C7 C8 3.3(4) . . . . ?
C5 C6 C7 C8 -178.8(2) . . . . ?
N1 C7 C8 C9 -120.9(3) . . . . ?
C6 C7 C8 C9 58.7(3) . . . . ?
N1 C7 C8 C13 54.3(3) . . . . ?
C6 C7 C8 C13 -126.1(3) . . . . ?
C13 C8 C9 C10 -0.4(4) . . . . ?
C7 C8 C9 C10 174.8(2) . . . . ?
C8 C9 C10 C11 1.0(4) . . . . ?
C9 C10 C11 C12 -1.2(4) . . . . ?
C9 C10 C11 C14 -178.4(3) . . . . ?
C10 C11 C12 C13 0.7(4) . . . . ?
C14 C11 C12 C13 178.0(3) . . . . ?
C11 C12 C13 C8 -0.1(4) . . . . ?
C9 C8 C13 C12 0.0(4) . . . . ?
C7 C8 C13 C12 -175.4(2) . . . . ?
C10 C11 C14 F3 -138.4(3) . . . . ?
C12 C11 C14 F3 44.4(4) . . . . ?
C10 C11 C14 F2 100.5(4) . . . . ?
C12 C11 C14 F2 -76.7(4) . . . . ?
C10 C11 C14 F1 -18.5(4) . . . . ?
C12 C11 C14 F1 164.3(3) . . . . ?
C7 N1 C15 N2 1.6(3) . . . . ?
C7 N1 C15 C16 -177.0(2) . . . . ?
N3 N2 C15 N1 -179.6(2) . . . . ?
C5 N2 C15 N1 0.0(3) . . . . ?
N3 N2 C15 C16 -0.7(3) . . . . ?
C5 N2 C15 C16 178.9(2) . . . . ?
N1 C15 C16 C17 179.2(2) . . . . ?
N2 C15 C16 C17 0.4(2) . . . . ?
N1 C15 C16 C21 0.5(5) . . . . ?
N2 C15 C16 C21 -178.3(3) . . . . ?
N2 N3 C17 C16 -0.4(3) . . . . ?
N2 N3 C17 C18 179.5(2) . . . . ?
C15 C16 C17 N3 0.0(3) . . . . ?
C21 C16 C17 N3 178.9(2) . . . . ?
C15 C16 C17 C18 -179.9(2) . . . . ?
C21 C16 C17 C18 -1.0(4) . . . . ?
N3 C17 C18 C19 -179.5(2) . . . . ?
C16 C17 C18 C19 0.4(4) . . . . ?
C17 C18 C19 C20 0.3(4) . . . . ?
C18 C19 C20 C21 -0.5(4) . . . . ?
C19 C20 C21 C16 -0.1(4) . . . . ?
C15 C16 C21 C20 179.3(3) . . . . ?
C17 C16 C21 C20 0.8(4) . . . . ?

_refine_diff_density_max         0.234
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.044



