# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_HBPD-CN
_database_code_depnum_ccdc_archive 'CCDC 2214982'
loop_
_audit_author_name
_audit_author_address
'cheng Liu'
;Jilin University
China
;
_audit_update_record             
;
2022-10-24 deposited with the CCDC.	2023-04-20 downloaded from the CCDC.
;
_audit_creation_date             2022-09-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H10 N2'
_chemical_formula_sum            'C18 H10 N2'
_chemical_formula_weight         254.28
_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'
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                   29.4976(15)
_cell_length_b                   4.2990(2)
_cell_length_c                   19.9989(10)
_cell_angle_alpha                90
_cell_angle_beta                 104.202(2)
_cell_angle_gamma                90
_cell_volume                     2458.6(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9908
_cell_measurement_temperature    101.0
_cell_measurement_theta_max      29.549
_cell_measurement_theta_min      2.813
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.082
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            34000
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.597
_diffrn_reflns_theta_min         2.813
_diffrn_ambient_temperature      101.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2605
_reflns_number_total             3412
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3412
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0433
_refine_ls_restrained_S_all      1.055
_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)+(0.0674P)²+1.6302P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1320
_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:
 C2(H2), C3(H3), C7(H7), C9(H9), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18)
;
_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
N1 N 0.71924(3) 0.5096(2) 0.66297(5) 0.0166(2) Uani 1 1 d . . . . .
N2 N 0.47440(4) -0.1794(3) 0.58457(6) 0.0350(3) Uani 1 1 d . . . . .
C1 C 0.69271(4) 0.6150(3) 0.60013(6) 0.0153(2) Uani 1 1 d . . . . .
C2 C 0.68999(4) 0.9340(3) 0.49999(6) 0.0196(2) Uani 1 1 d . . . . .
H2 H 0.7048 1.0723 0.4749 0.023 Uiso 1 1 calc R U . . .
C3 C 0.57811(4) 0.2078(3) 0.59071(5) 0.0162(2) Uani 1 1 d . . . . .
H3 H 0.5595 0.2745 0.5473 0.019 Uiso 1 1 calc R U . . .
C4 C 0.65258(3) 0.2076(3) 0.67725(5) 0.0140(2) Uani 1 1 d . . . . .
C5 C 0.55963(4) 0.0118(3) 0.63074(6) 0.0167(2) Uani 1 1 d . . . . .
C6 C 0.63343(4) -0.0025(3) 0.71965(5) 0.0146(2) Uani 1 1 d . . . . .
C7 C 0.71433(4) 0.8211(3) 0.56271(6) 0.0181(2) Uani 1 1 d . . . . .
H7 H 0.7459 0.8821 0.5810 0.022 Uiso 1 1 calc R U . . .
C8 C 0.64567(4) 0.5233(3) 0.57314(5) 0.0141(2) Uani 1 1 d . . . . .
C9 C 0.65981(4) -0.1183(3) 0.78389(6) 0.0168(2) Uani 1 1 d . . . . .
H9 H 0.6916 -0.0590 0.8003 0.020 Uiso 1 1 calc R U . . .
C10 C 0.62523(4) 0.3130(3) 0.61359(5) 0.0140(2) Uani 1 1 d . . . . .
C11 C 0.64303(4) 0.8449(3) 0.47273(6) 0.0190(2) Uani 1 1 d . . . . .
H11 H 0.6263 0.9248 0.4294 0.023 Uiso 1 1 calc R U . . .
C12 C 0.58617(4) -0.0994(3) 0.69665(5) 0.0152(2) Uani 1 1 d . . . . .
C13 C 0.59276(4) -0.4056(3) 0.80008(6) 0.0207(3) Uani 1 1 d . . . . .
H13 H 0.5792 -0.5391 0.8277 0.025 Uiso 1 1 calc R U . . .
C14 C 0.62143(4) 0.6436(3) 0.50831(6) 0.0171(2) Uani 1 1 d . . . . .
H14 H 0.5899 0.5845 0.4892 0.020 Uiso 1 1 calc R U . . .
C15 C 0.69980(4) 0.3185(3) 0.69843(6) 0.0164(2) Uani 1 1 d . . . . .
H15 H 0.7183 0.2475 0.7415 0.020 Uiso 1 1 calc R U . . .
C16 C 0.56643(4) -0.2997(3) 0.73774(6) 0.0184(2) Uani 1 1 d . . . . .
H16 H 0.5347 -0.3618 0.7222 0.022 Uiso 1 1 calc R U . . .
C17 C 0.51206(4) -0.0931(3) 0.60514(6) 0.0225(3) Uani 1 1 d . . . . .
C18 C 0.63988(4) -0.3151(3) 0.82266(6) 0.0189(2) Uani 1 1 d . . . . .
H18 H 0.6582 -0.3912 0.8654 0.023 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
N1 C1 1.3836(14) . ?
N1 C15 1.3064(15) . ?
N2 C17 1.1473(16) . ?
C1 C7 1.4091(16) . ?
C1 C8 1.4158(14) . ?
C2 H2 0.9500 . ?
C2 C7 1.3721(16) . ?
C2 C11 1.4116(16) . ?
C3 H3 0.9500 . ?
C3 C5 1.3646(16) . ?
C3 C10 1.4262(14) . ?
C4 C6 1.4451(16) . ?
C4 C10 1.4046(14) . ?
C4 C15 1.4345(14) . ?
C5 C12 1.4397(15) . ?
C5 C17 1.4431(15) . ?
C6 C9 1.4188(15) . ?
C6 C12 1.4194(14) . ?
C7 H7 0.9500 . ?
C8 C10 1.4404(15) . ?
C8 C14 1.4161(15) . ?
C9 H9 0.9500 . ?
C9 C18 1.3735(17) . ?
C11 H11 0.9500 . ?
C11 C14 1.3723(16) . ?
C12 C16 1.4106(16) . ?
C13 H13 0.9500 . ?
C13 C16 1.3747(16) . ?
C13 C18 1.4067(16) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 H18 0.9500 . ?

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
C15 N1 C1 118.25(9) . . ?
N1 C1 C7 117.35(10) . . ?
N1 C1 C8 122.55(10) . . ?
C7 C1 C8 120.10(10) . . ?
C7 C2 H2 120.0 . . ?
C7 C2 C11 120.05(11) . . ?
C11 C2 H2 120.0 . . ?
C5 C3 H3 119.8 . . ?
C5 C3 C10 120.37(10) . . ?
C10 C3 H3 119.8 . . ?
C10 C4 C6 120.88(9) . . ?
C10 C4 C15 117.43(10) . . ?
C15 C4 C6 121.69(10) . . ?
C3 C5 C12 122.46(10) . . ?
C3 C5 C17 118.58(10) . . ?
C12 C5 C17 118.94(10) . . ?
C9 C6 C4 122.97(10) . . ?
C9 C6 C12 117.85(10) . . ?
C12 C6 C4 119.18(10) . . ?
C1 C7 H7 119.9 . . ?
C2 C7 C1 120.30(10) . . ?
C2 C7 H7 119.9 . . ?
C1 C8 C10 117.83(10) . . ?
C1 C8 C14 118.35(10) . . ?
C14 C8 C10 123.82(10) . . ?
C6 C9 H9 119.6 . . ?
C18 C9 C6 120.78(10) . . ?
C18 C9 H9 119.6 . . ?
C3 C10 C8 121.88(10) . . ?
C4 C10 C3 119.10(10) . . ?
C4 C10 C8 119.02(9) . . ?
C2 C11 H11 119.8 . . ?
C14 C11 C2 120.49(10) . . ?
C14 C11 H11 119.8 . . ?
C6 C12 C5 117.99(10) . . ?
C16 C12 C5 121.78(10) . . ?
C16 C12 C6 120.23(10) . . ?
C16 C13 H13 120.2 . . ?
C16 C13 C18 119.57(11) . . ?
C18 C13 H13 120.2 . . ?
C8 C14 H14 119.6 . . ?
C11 C14 C8 120.70(10) . . ?
C11 C14 H14 119.6 . . ?
N1 C15 C4 124.92(10) . . ?
N1 C15 H15 117.5 . . ?
C4 C15 H15 117.5 . . ?
C12 C16 H16 119.7 . . ?
C13 C16 C12 120.55(10) . . ?
C13 C16 H16 119.7 . . ?
N2 C17 C5 179.30(16) . . ?
C9 C18 C13 121.01(10) . . ?
C9 C18 H18 119.5 . . ?
C13 C18 H18 119.5 . . ?

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
N1 C1 C7 C2 179.90(11) . . . . ?
N1 C1 C8 C10 0.29(16) . . . . ?
N1 C1 C8 C14 -179.93(10) . . . . ?
C1 N1 C15 C4 -0.01(17) . . . . ?
C1 C8 C10 C3 179.94(10) . . . . ?
C1 C8 C10 C4 -0.32(15) . . . . ?
C1 C8 C14 C11 -0.16(17) . . . . ?
C2 C11 C14 C8 0.40(18) . . . . ?
C3 C5 C12 C6 -0.81(17) . . . . ?
C3 C5 C12 C16 179.39(11) . . . . ?
C4 C6 C9 C18 179.32(10) . . . . ?
C4 C6 C12 C5 1.41(16) . . . . ?
C4 C6 C12 C16 -178.78(10) . . . . ?
C5 C3 C10 C4 1.15(17) . . . . ?
C5 C3 C10 C8 -179.11(10) . . . . ?
C5 C12 C16 C13 179.15(11) . . . . ?
C6 C4 C10 C3 -0.52(16) . . . . ?
C6 C4 C10 C8 179.74(10) . . . . ?
C6 C4 C15 N1 -179.57(10) . . . . ?
C6 C9 C18 C13 -0.44(18) . . . . ?
C6 C12 C16 C13 -0.65(17) . . . . ?
C7 C1 C8 C10 -179.81(10) . . . . ?
C7 C1 C8 C14 -0.04(16) . . . . ?
C7 C2 C11 C14 -0.44(18) . . . . ?
C8 C1 C7 C2 0.00(17) . . . . ?
C9 C6 C12 C5 -178.57(10) . . . . ?
C9 C6 C12 C16 1.23(16) . . . . ?
C10 C3 C5 C12 -0.49(18) . . . . ?
C10 C3 C5 C17 -178.98(11) . . . . ?
C10 C4 C6 C9 179.20(10) . . . . ?
C10 C4 C6 C12 -0.78(16) . . . . ?
C10 C4 C15 N1 -0.04(17) . . . . ?
C10 C8 C14 C11 179.60(11) . . . . ?
C11 C2 C7 C1 0.23(18) . . . . ?
C12 C6 C9 C18 -0.70(17) . . . . ?
C14 C8 C10 C3 0.18(17) . . . . ?
C14 C8 C10 C4 179.91(10) . . . . ?
C15 N1 C1 C7 179.98(10) . . . . ?
C15 N1 C1 C8 -0.13(17) . . . . ?
C15 C4 C6 C9 -1.28(17) . . . . ?
C15 C4 C6 C12 178.74(10) . . . . ?
C15 C4 C10 C3 179.95(10) . . . . ?
C15 C4 C10 C8 0.21(16) . . . . ?
C16 C13 C18 C9 1.05(18) . . . . ?
C17 C5 C12 C6 177.67(10) . . . . ?
C17 C5 C12 C16 -2.13(17) . . . . ?
C18 C13 C16 C12 -0.50(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_z-fphqla
_database_code_depnum_ccdc_archive 'CCDC 2214985'
loop_
_audit_author_name
_audit_author_address
'cheng Liu'
;Jilin University
China
;
_audit_update_record             
;
2022-10-24 deposited with the CCDC.	2023-04-20 downloaded from the CCDC.
;
_audit_creation_date             2022-09-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H11 F N2'
_chemical_formula_sum            'C18 H11 F N2'
_chemical_formula_weight         274.29
_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           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                   7.2368(6)
_cell_length_b                   5.0575(4)
_cell_length_c                   36.437(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.354(3)
_cell_angle_gamma                90
_cell_volume                     1327.78(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9801
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.494
_cell_measurement_theta_min      2.827
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.092
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            27124
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.617
_diffrn_reflns_theta_min         2.827
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_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                3000
_reflns_number_total             3654
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.253
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3654
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1237
_refine_ls_R_factor_gt           0.1067
_refine_ls_restrained_S_all      1.253
_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)+5.2225P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2113
_refine_ls_wR_factor_ref         0.2173
_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:
 C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C11(H11), C12(H12), C15(H15),
 C16(H16), C17(H17), C18(H18)
;
_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
F1 F 0.7952(3) 1.4099(5) 0.50150(6) 0.0351(6) Uani 1 1 d . . . . .
N1 N 0.2824(4) 0.5102(7) 0.59984(8) 0.0282(7) Uani 1 1 d . . . . .
N2 N 0.6666(4) 0.0135(6) 0.72088(7) 0.0216(6) Uani 1 1 d . . . . .
C1 C 0.7566(5) 1.2263(8) 0.52703(9) 0.0244(7) Uani 1 1 d . . . . .
C2 C 0.5747(5) 1.1953(8) 0.53461(9) 0.0241(7) Uani 1 1 d . . . . .
H2 H 0.4790 1.3017 0.5227 0.029 Uiso 1 1 calc R U . . .
C3 C 0.5351(5) 1.0045(7) 0.56013(9) 0.0223(7) Uani 1 1 d . . . . .
H3 H 0.4107 0.9810 0.5658 0.027 Uiso 1 1 calc R U . . .
C4 C 0.6752(5) 0.8467(7) 0.57760(8) 0.0184(6) Uani 1 1 d . . . . .
C5 C 0.8579(5) 0.8832(8) 0.56887(9) 0.0250(8) Uani 1 1 d . . . . .
H5 H 0.9544 0.7757 0.5803 0.030 Uiso 1 1 calc R U . . .
C6 C 0.8992(5) 1.0755(8) 0.54361(10) 0.0262(8) Uani 1 1 d . . . . .
H6 H 1.0233 1.1022 0.5379 0.031 Uiso 1 1 calc R U . . .
C7 C 0.6303(5) 0.6467(7) 0.60534(9) 0.0179(6) Uani 1 1 d . . . . .
C8 C 0.4365(5) 0.5664(7) 0.60321(9) 0.0211(7) Uani 1 1 d . . . . .
C9 C 0.7545(4) 0.5438(7) 0.63117(9) 0.0179(6) Uani 1 1 d . . . . .
H9 H 0.8794 0.5993 0.6303 0.021 Uiso 1 1 calc R U . . .
C10 C 0.7208(4) 0.3554(7) 0.66068(9) 0.0184(7) Uani 1 1 d . . . . .
C11 C 0.5665(5) 0.3705(8) 0.68018(9) 0.0216(7) Uani 1 1 d . . . . .
H11 H 0.4729 0.4979 0.6734 0.026 Uiso 1 1 calc R U . . .
C12 C 0.5468(5) 0.1987(8) 0.70996(9) 0.0215(7) Uani 1 1 d . . . . .
H12 H 0.4398 0.2179 0.7230 0.026 Uiso 1 1 calc R U . . .
C13 C 0.8232(5) -0.0050(7) 0.70215(8) 0.0182(7) Uani 1 1 d . . . . .
C14 C 0.8571(4) 0.1618(7) 0.67223(8) 0.0172(6) Uani 1 1 d . . . . .
C15 C 1.0259(5) 0.1280(7) 0.65554(9) 0.0207(7) Uani 1 1 d . . . . .
H15 H 1.0503 0.2355 0.6352 0.025 Uiso 1 1 calc R U . . .
C16 C 1.1537(5) -0.0582(8) 0.66853(9) 0.0226(7) Uani 1 1 d . . . . .
H16 H 1.2664 -0.0762 0.6573 0.027 Uiso 1 1 calc R U . . .
C17 C 1.1189(5) -0.2228(8) 0.69835(9) 0.0224(7) Uani 1 1 d . . . . .
H17 H 1.2085 -0.3503 0.7072 0.027 Uiso 1 1 calc R U . . .
C18 C 0.9558(5) -0.1995(8) 0.71465(9) 0.0237(7) Uani 1 1 d . . . . .
H18 H 0.9318 -0.3139 0.7343 0.028 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 C1 1.361(4) . ?
N1 C8 1.146(5) . ?
N2 C12 1.313(5) . ?
N2 C13 1.379(4) . ?
C1 C2 1.379(5) . ?
C1 C6 1.377(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.396(5) . ?
C4 C5 1.401(5) . ?
C4 C7 1.487(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.455(5) . ?
C7 C9 1.344(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.474(5) . ?
C10 C11 1.380(5) . ?
C10 C14 1.425(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.408(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.418(4) . ?
C13 C18 1.419(5) . ?
C14 C15 1.425(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.372(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.410(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.375(5) . ?
C18 H18 0.9500 . ?

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
C12 N2 C13 116.6(3) . . ?
F1 C1 C2 118.4(3) . . ?
F1 C1 C6 119.0(3) . . ?
C6 C1 C2 122.6(3) . . ?
C1 C2 H2 120.9 . . ?
C1 C2 C3 118.3(3) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.1(3) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 118.8(3) . . ?
C3 C4 C7 120.2(3) . . ?
C5 C4 C7 121.0(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.5(3) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.7(3) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C8 C7 C4 115.1(3) . . ?
C9 C7 C4 124.4(3) . . ?
C9 C7 C8 120.5(3) . . ?
N1 C8 C7 176.5(4) . . ?
C7 C9 H9 116.0 . . ?
C7 C9 C10 128.0(3) . . ?
C10 C9 H9 116.0 . . ?
C11 C10 C9 122.4(3) . . ?
C11 C10 C14 117.2(3) . . ?
C14 C10 C9 120.1(3) . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.5(3) . . ?
C12 C11 H11 119.8 . . ?
N2 C12 C11 124.2(3) . . ?
N2 C12 H12 117.9 . . ?
C11 C12 H12 117.9 . . ?
N2 C13 C14 123.3(3) . . ?
N2 C13 C18 116.8(3) . . ?
C14 C13 C18 119.9(3) . . ?
C13 C14 C10 118.1(3) . . ?
C13 C14 C15 118.3(3) . . ?
C15 C14 C10 123.6(3) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.8(3) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.5(3) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.3(3) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 H18 119.9 . . ?
C17 C18 C13 120.2(3) . . ?
C17 C18 H18 119.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 F1 0.95 2.55 3.497(4) 172.7 3_686

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
F1 C1 C2 C3 178.8(3) . . . . ?
F1 C1 C6 C5 -178.2(3) . . . . ?
N2 C13 C14 C10 -1.0(5) . . . . ?
N2 C13 C14 C15 178.6(3) . . . . ?
N2 C13 C18 C17 -177.4(3) . . . . ?
C1 C2 C3 C4 -0.3(5) . . . . ?
C2 C1 C6 C5 0.3(6) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
C2 C3 C4 C7 178.9(3) . . . . ?
C3 C4 C5 C6 0.8(5) . . . . ?
C3 C4 C7 C8 20.4(5) . . . . ?
C3 C4 C7 C9 -159.0(3) . . . . ?
C4 C5 C6 C1 -0.9(6) . . . . ?
C4 C7 C9 C10 176.8(3) . . . . ?
C5 C4 C7 C8 -160.5(3) . . . . ?
C5 C4 C7 C9 20.0(5) . . . . ?
C6 C1 C2 C3 0.3(6) . . . . ?
C7 C4 C5 C6 -178.3(3) . . . . ?
C7 C9 C10 C11 -39.7(5) . . . . ?
C7 C9 C10 C14 145.7(4) . . . . ?
C8 C7 C9 C10 -2.6(6) . . . . ?
C9 C10 C11 C12 -175.2(3) . . . . ?
C9 C10 C14 C13 176.4(3) . . . . ?
C9 C10 C14 C15 -3.2(5) . . . . ?
C10 C11 C12 N2 -1.3(6) . . . . ?
C10 C14 C15 C16 178.4(3) . . . . ?
C11 C10 C14 C13 1.5(5) . . . . ?
C11 C10 C14 C15 -178.1(3) . . . . ?
C12 N2 C13 C14 -0.7(5) . . . . ?
C12 N2 C13 C18 178.1(3) . . . . ?
C13 N2 C12 C11 1.8(5) . . . . ?
C13 C14 C15 C16 -1.1(5) . . . . ?
C14 C10 C11 C12 -0.5(5) . . . . ?
C14 C13 C18 C17 1.4(5) . . . . ?
C14 C15 C16 C17 1.0(5) . . . . ?
C15 C16 C17 C18 0.3(5) . . . . ?
C16 C17 C18 C13 -1.6(5) . . . . ?
C18 C13 C14 C10 -179.7(3) . . . . ?
C18 C13 C14 C15 -0.1(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_z-cf3phqla
_database_code_depnum_ccdc_archive 'CCDC 2214984'
loop_
_audit_author_name
_audit_author_address
'cheng Liu'
;Jilin University
China
;
_audit_update_record             
;
2022-10-24 deposited with the CCDC.	2023-04-20 downloaded from the CCDC.
;
_audit_creation_date             2022-09-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H11 F3 N2'
_chemical_formula_sum            'C19 H11 F3 N2'
_chemical_formula_weight         324.30
_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'
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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9801(7)
_cell_length_b                   9.2324(9)
_cell_length_c                   12.0514(13)
_cell_angle_alpha                84.242(4)
_cell_angle_beta                 86.465(4)
_cell_angle_gamma                76.598(4)
_cell_volume                     751.08(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9854
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      31.487
_cell_measurement_theta_min      2.960
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.112
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20671
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.556
_diffrn_reflns_theta_min         2.718
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_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                4254
_reflns_number_total             4984
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4984
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      1.053
_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)+(0.0525P)²+0.3595P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1218
_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:
 C3(H3), C4(H4), C7(H7), C10(H10), C11(H11), C12(H12), C14(H14), C16(H16),
 C17(H17), C18(H18), C19(H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
F1 F 1.59257(14) 0.83121(10) 0.53664(8) 0.0390(2) Uani 1 1 d . . . . .
F2 F 1.31279(17) 0.92377(9) 0.61540(7) 0.0405(2) Uani 1 1 d . . . . .
F3 F 1.32766(13) 0.86101(8) 0.44754(6) 0.02989(19) Uani 1 1 d . . . . .
N1 N 0.94830(16) 0.21174(12) 0.73650(10) 0.0259(2) Uani 1 1 d . . . . .
N2 N 1.41802(14) -0.27417(11) 0.98330(8) 0.01907(19) Uani 1 1 d . . . . .
C1 C 1.4042(2) 0.82031(13) 0.54762(10) 0.0221(2) Uani 1 1 d . . . . .
C2 C 1.38466(17) 0.66712(11) 0.59353(9) 0.0169(2) Uani 1 1 d . . . . .
C3 C 1.24391(18) 0.60349(13) 0.55443(10) 0.0217(2) Uani 1 1 d . . . . .
H3 H 1.1659 0.6527 0.4939 0.026 Uiso 1 1 calc R U . . .
C4 C 1.21783(17) 0.46666(13) 0.60456(10) 0.0207(2) Uani 1 1 d . . . . .
H4 H 1.1204 0.4231 0.5785 0.025 Uiso 1 1 calc R U . . .
C5 C 1.33320(15) 0.39257(11) 0.69278(9) 0.01418(19) Uani 1 1 d . . . . .
C6 C 1.30473(15) 0.24637(11) 0.74631(9) 0.01414(19) Uani 1 1 d . . . . .
C7 C 1.45290(15) 0.14153(11) 0.79369(9) 0.01438(19) Uani 1 1 d . . . . .
H7 H 1.5801 0.1629 0.7865 0.017 Uiso 1 1 calc R U . . .
C8 C 1.43896(15) -0.00151(11) 0.85495(8) 0.01394(18) Uani 1 1 d . . . . .
C9 C 1.60442(15) -0.12712(11) 0.85589(8) 0.01293(18) Uani 1 1 d . . . . .
C10 C 1.78485(15) -0.12553(12) 0.79492(9) 0.0168(2) Uani 1 1 d . . . . .
H10 H 1.7992 -0.0384 0.7491 0.020 Uiso 1 1 calc R U . . .
C11 C 1.93888(17) -0.24934(13) 0.80177(10) 0.0215(2) Uani 1 1 d . . . . .
H11 H 2.0597 -0.2464 0.7617 0.026 Uiso 1 1 calc R U . . .
C12 C 1.91928(17) -0.38103(13) 0.86789(10) 0.0224(2) Uani 1 1 d . . . . .
H12 H 2.0267 -0.4659 0.8717 0.027 Uiso 1 1 calc R U . . .
C13 C 1.10833(16) 0.22262(12) 0.74197(9) 0.0177(2) Uani 1 1 d . . . . .
C14 C 1.74620(17) -0.38695(12) 0.92657(9) 0.0190(2) Uani 1 1 d . . . . .
H14 H 1.7336 -0.4761 0.9702 0.023 Uiso 1 1 calc R U . . .
C15 C 1.58605(15) -0.26039(11) 0.92225(9) 0.01467(19) Uani 1 1 d . . . . .
C16 C 1.27033(17) -0.15617(14) 0.98037(10) 0.0223(2) Uani 1 1 d . . . . .
H16 H 1.1530 -0.1643 1.0224 0.027 Uiso 1 1 calc R U . . .
C17 C 1.27395(16) -0.01820(13) 0.91907(10) 0.0196(2) Uani 1 1 d . . . . .
H17 H 1.1625 0.0632 0.9221 0.024 Uiso 1 1 calc R U . . .
C18 C 1.47533(16) 0.45808(12) 0.73108(9) 0.0165(2) Uani 1 1 d . . . . .
H18 H 1.5538 0.4092 0.7915 0.020 Uiso 1 1 calc R U . . .
C19 C 1.50201(17) 0.59454(12) 0.68088(9) 0.0181(2) Uani 1 1 d . . . . .
H19 H 1.6001 0.6382 0.7061 0.022 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 C1 1.3393(16) . ?
F2 C1 1.3404(15) . ?
F3 C1 1.3329(14) . ?
N1 C13 1.1509(15) . ?
N2 C15 1.3701(14) . ?
N2 C16 1.3142(15) . ?
C1 C2 1.4994(15) . ?
C2 C3 1.3829(16) . ?
C2 C19 1.3923(15) . ?
C3 H3 0.9500 . ?
C3 C4 1.3906(15) . ?
C4 H4 0.9500 . ?
C4 C5 1.3969(14) . ?
C5 C6 1.4870(14) . ?
C5 C18 1.3978(15) . ?
C6 C7 1.3530(14) . ?
C6 C13 1.4424(15) . ?
C7 H7 0.9500 . ?
C7 C8 1.4675(14) . ?
C8 C9 1.4342(14) . ?
C8 C17 1.3769(15) . ?
C9 C10 1.4207(14) . ?
C9 C15 1.4258(14) . ?
C10 H10 0.9500 . ?
C10 C11 1.3754(15) . ?
C11 H11 0.9500 . ?
C11 C12 1.4146(16) . ?
C12 H12 0.9500 . ?
C12 C14 1.3711(17) . ?
C14 H14 0.9500 . ?
C14 C15 1.4167(14) . ?
C16 H16 0.9500 . ?
C16 C17 1.4117(15) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C18 C19 1.3891(14) . ?
C19 H19 0.9500 . ?

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
C16 N2 C15 116.93(9) . . ?
F1 C1 F2 106.42(10) . . ?
F1 C1 C2 112.20(10) . . ?
F2 C1 C2 111.13(10) . . ?
F3 C1 F1 106.72(10) . . ?
F3 C1 F2 107.04(10) . . ?
F3 C1 C2 112.93(10) . . ?
C3 C2 C1 120.40(10) . . ?
C3 C2 C19 120.73(10) . . ?
C19 C2 C1 118.74(10) . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.31(10) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.80(10) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 120.67(9) . . ?
C4 C5 C18 119.19(9) . . ?
C18 C5 C6 120.14(9) . . ?
C7 C6 C5 122.62(9) . . ?
C7 C6 C13 122.19(9) . . ?
C13 C6 C5 115.18(9) . . ?
C6 C7 H7 116.4 . . ?
C6 C7 C8 127.21(10) . . ?
C8 C7 H7 116.4 . . ?
C9 C8 C7 120.40(9) . . ?
C17 C8 C7 122.01(9) . . ?
C17 C8 C9 117.45(9) . . ?
C10 C9 C8 123.64(9) . . ?
C10 C9 C15 118.51(9) . . ?
C15 C9 C8 117.85(9) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.40(10) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.67(10) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 119.8 . . ?
C14 C12 C11 120.40(10) . . ?
C14 C12 H12 119.8 . . ?
N1 C13 C6 176.28(11) . . ?
C12 C14 H14 119.9 . . ?
C12 C14 C15 120.13(10) . . ?
C15 C14 H14 119.9 . . ?
N2 C15 C9 123.18(9) . . ?
N2 C15 C14 116.94(9) . . ?
C14 C15 C9 119.88(10) . . ?
N2 C16 H16 117.7 . . ?
N2 C16 C17 124.52(10) . . ?
C17 C16 H16 117.7 . . ?
C8 C17 C16 120.05(10) . . ?
C8 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C5 C18 H18 120.0 . . ?
C19 C18 C5 120.08(10) . . ?
C19 C18 H18 120.0 . . ?
C2 C19 H19 120.1 . . ?
C18 C19 C2 119.86(10) . . ?
C18 C19 H19 120.1 . . ?

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
F1 C1 C2 C3 -141.88(12) . . . . ?
F1 C1 C2 C19 42.16(15) . . . . ?
F2 C1 C2 C3 99.11(14) . . . . ?
F2 C1 C2 C19 -76.86(14) . . . . ?
F3 C1 C2 C3 -21.21(16) . . . . ?
F3 C1 C2 C19 162.83(11) . . . . ?
N2 C16 C17 C8 1.3(2) . . . . ?
C1 C2 C3 C4 -174.79(11) . . . . ?
C1 C2 C19 C18 174.65(10) . . . . ?
C2 C3 C4 C5 -0.66(19) . . . . ?
C3 C2 C19 C18 -1.30(17) . . . . ?
C3 C4 C5 C6 179.91(11) . . . . ?
C3 C4 C5 C18 0.43(18) . . . . ?
C4 C5 C6 C7 150.49(11) . . . . ?
C4 C5 C6 C13 -28.17(15) . . . . ?
C4 C5 C18 C19 -0.62(17) . . . . ?
C5 C6 C7 C8 175.63(10) . . . . ?
C5 C18 C19 C2 1.06(17) . . . . ?
C6 C5 C18 C19 179.89(10) . . . . ?
C6 C7 C8 C9 151.05(11) . . . . ?
C6 C7 C8 C17 -33.28(17) . . . . ?
C7 C8 C9 C10 -3.40(16) . . . . ?
C7 C8 C9 C15 176.32(9) . . . . ?
C7 C8 C17 C16 -177.29(11) . . . . ?
C8 C9 C10 C11 178.58(11) . . . . ?
C8 C9 C15 N2 0.91(15) . . . . ?
C8 C9 C15 C14 -179.45(10) . . . . ?
C9 C8 C17 C16 -1.50(17) . . . . ?
C9 C10 C11 C12 1.13(18) . . . . ?
C10 C9 C15 N2 -179.35(10) . . . . ?
C10 C9 C15 C14 0.28(15) . . . . ?
C10 C11 C12 C14 -0.23(19) . . . . ?
C11 C12 C14 C15 -0.63(18) . . . . ?
C12 C14 C15 N2 -179.75(11) . . . . ?
C12 C14 C15 C9 0.59(17) . . . . ?
C13 C6 C7 C8 -5.80(18) . . . . ?
C15 N2 C16 C17 0.04(19) . . . . ?
C15 C9 C10 C11 -1.14(16) . . . . ?
C16 N2 C15 C9 -1.16(16) . . . . ?
C16 N2 C15 C14 179.19(11) . . . . ?
C17 C8 C9 C10 -179.26(11) . . . . ?
C17 C8 C9 C15 0.46(15) . . . . ?
C18 C5 C6 C7 -30.03(16) . . . . ?
C18 C5 C6 C13 151.31(10) . . . . ?
C19 C2 C3 C4 1.10(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_FBPD-CN
_database_code_depnum_ccdc_archive 'CCDC 2214983'
loop_
_audit_author_name
_audit_author_address
'cheng Liu'
;Jilin University
China
;
_audit_update_record             
;
2022-10-24 deposited with the CCDC.	2023-04-20 downloaded from the CCDC.
;
_audit_creation_date             2022-10-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H9 F N2, 1.2[H2O]'
_chemical_formula_sum            'C18 H9 F N2'
_chemical_formula_weight         272.27
_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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.7431(7)
_cell_length_b                   12.294(3)
_cell_length_c                   14.717(3)
_cell_angle_alpha                88.588(12)
_cell_angle_beta                 88.971(8)
_cell_angle_gamma                87.456(7)
_cell_volume                     676.3(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6763
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      29.965
_cell_measurement_theta_min      2.769
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.090
_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            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18076
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.017
_diffrn_reflns_theta_min         2.769
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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                2815
_reflns_number_total             3951
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3951
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0461
_refine_ls_restrained_S_all      1.045
_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)+(0.0809P)²+0.0489P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1270
_refine_ls_wR_factor_ref         0.1425
_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:
 C1(H1), C3(H3), C8(H8), C9(H9), C10(H10), C12(H12), C15(H15), C17(H17),
 C18(H18)
;
_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
F1 F 0.0532(2) 0.10393(5) 0.89212(5) 0.0284(2) Uani 1 1 d . . . . .
N1 N 0.8551(3) 0.34190(9) 0.49028(7) 0.0291(3) Uani 1 1 d . . . . .
N2 N 0.2774(3) 0.61292(7) 0.93237(6) 0.0195(2) Uani 1 1 d . . . . .
C1 C 0.3025(3) 0.14141(9) 0.74704(8) 0.0228(2) Uani 1 1 d . . . . .
H1 H 0.2871 0.0672 0.7317 0.027 Uiso 1 1 calc R U . . .
C21 C 0.1873(3) 0.17809(9) 0.83221(8) 0.0207(2) Uani 1 1 d . . . . .
C3 C 0.2019(3) 0.28377(9) 0.85805(7) 0.0186(2) Uani 1 1 d . . . . .
H3 H 0.1186 0.3049 0.9166 0.022 Uiso 1 1 calc R U . . .
C4 C 0.3435(3) 0.36120(9) 0.79601(7) 0.0162(2) Uani 1 1 d . . . . .
C5 C 0.3734(3) 0.47426(8) 0.81853(7) 0.0158(2) Uani 1 1 d . . . . .
C6 C 0.5192(3) 0.54939(9) 0.75617(7) 0.0166(2) Uani 1 1 d . . . . .
C7 C 0.5489(3) 0.66041(9) 0.78386(7) 0.0177(2) Uani 1 1 d . . . . .
C8 C 0.6974(3) 0.74280(9) 0.72780(8) 0.0215(2) Uani 1 1 d . . . . .
H8 H 0.7764 0.7266 0.6677 0.026 Uiso 1 1 calc R U . . .
C9 C 0.7278(3) 0.84625(9) 0.75990(9) 0.0243(3) Uani 1 1 d . . . . .
H9 H 0.8289 0.9007 0.7218 0.029 Uiso 1 1 calc R U . . .
C10 C 0.6110(3) 0.87221(9) 0.84836(9) 0.0246(3) Uani 1 1 d . . . . .
H10 H 0.6356 0.9437 0.8699 0.030 Uiso 1 1 calc R U . . .
C11 C 0.4640(3) 0.32641(9) 0.70894(7) 0.0175(2) Uani 1 1 d . . . . .
C12 C 0.4389(3) 0.21603(9) 0.68592(8) 0.0214(2) Uani 1 1 d . . . . .
H12 H 0.5173 0.1930 0.6274 0.026 Uiso 1 1 calc R U . . .
C13 C 0.6114(3) 0.40585(9) 0.64703(7) 0.0184(2) Uani 1 1 d . . . . .
C14 C 0.7450(3) 0.37090(9) 0.55923(8) 0.0216(2) Uani 1 1 d . . . . .
C15 C 0.6381(3) 0.51273(9) 0.66913(7) 0.0184(2) Uani 1 1 d . . . . .
H15 H 0.7363 0.5627 0.6263 0.022 Uiso 1 1 calc R U . . .
C16 C 0.4282(3) 0.68758(9) 0.87272(7) 0.0180(2) Uani 1 1 d . . . . .
C17 C 0.2551(3) 0.51280(9) 0.90530(7) 0.0181(2) Uani 1 1 d . . . . .
H17 H 0.1523 0.4619 0.9465 0.022 Uiso 1 1 calc R U . . .
C18 C 0.4613(3) 0.79434(9) 0.90380(8) 0.0216(2) Uani 1 1 d . . . . .
H18 H 0.3798 0.8124 0.9633 0.026 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 C21 1.3585(13) . ?
N1 C14 1.1475(15) . ?
N2 C16 1.3856(14) . ?
N2 C17 1.3097(14) . ?
C1 H1 0.9500 . ?
C1 C21 1.3970(16) . ?
C1 C12 1.3769(16) . ?
C21 C3 1.3664(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.4160(15) . ?
C4 C5 1.4464(15) . ?
C4 C11 1.4204(15) . ?
C5 C6 1.4066(15) . ?
C5 C17 1.4292(15) . ?
C6 C7 1.4436(15) . ?
C6 C15 1.4255(15) . ?
C7 C8 1.4170(15) . ?
C7 C16 1.4187(15) . ?
C8 H8 0.9500 . ?
C8 C9 1.3777(16) . ?
C9 H9 0.9500 . ?
C9 C10 1.4055(17) . ?
C10 H10 0.9500 . ?
C10 C18 1.3745(16) . ?
C11 C12 1.4142(15) . ?
C11 C13 1.4403(15) . ?
C12 H12 0.9500 . ?
C13 C14 1.4455(15) . ?
C13 C15 1.3698(16) . ?
C15 H15 0.9500 . ?
C16 C18 1.4118(15) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?

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
C17 N2 C16 117.81(10) . . ?
C21 C1 H1 121.0 . . ?
C12 C1 H1 121.0 . . ?
C12 C1 C21 118.05(10) . . ?
F1 C21 C1 117.67(10) . . ?
F1 C21 C3 118.67(10) . . ?
C3 C21 C1 123.65(10) . . ?
C21 C3 H3 120.6 . . ?
C21 C3 C4 118.86(10) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 C5 122.32(10) . . ?
C3 C4 C11 118.86(10) . . ?
C11 C4 C5 118.82(9) . . ?
C6 C5 C4 121.28(10) . . ?
C6 C5 C17 118.03(10) . . ?
C17 C5 C4 120.68(9) . . ?
C5 C6 C7 118.39(10) . . ?
C5 C6 C15 118.95(10) . . ?
C15 C6 C7 122.64(10) . . ?
C8 C7 C6 123.58(10) . . ?
C8 C7 C16 118.47(10) . . ?
C16 C7 C6 117.94(10) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.37(11) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.81(11) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 120.0 . . ?
C18 C10 C9 120.09(11) . . ?
C18 C10 H10 120.0 . . ?
C4 C11 C13 118.19(10) . . ?
C12 C11 C4 119.62(10) . . ?
C12 C11 C13 122.19(10) . . ?
C1 C12 C11 120.96(10) . . ?
C1 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C11 C13 C14 118.78(10) . . ?
C15 C13 C11 122.45(10) . . ?
C15 C13 C14 118.75(10) . . ?
N1 C14 C13 178.81(13) . . ?
C6 C15 H15 119.8 . . ?
C13 C15 C6 120.30(10) . . ?
C13 C15 H15 119.8 . . ?
N2 C16 C7 122.76(10) . . ?
N2 C16 C18 117.24(10) . . ?
C18 C16 C7 119.99(10) . . ?
N2 C17 C5 125.04(10) . . ?
N2 C17 H17 117.5 . . ?
C5 C17 H17 117.5 . . ?
C10 C18 C16 120.26(11) . . ?
C10 C18 H18 119.9 . . ?
C16 C18 H18 119.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C17 H17 N2 0.95 2.56 3.4626(15) 158.6 2_567

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
F1 C21 C3 C4 179.64(9) . . . . ?
N2 C16 C18 C10 179.49(10) . . . . ?
C1 C21 C3 C4 -0.50(18) . . . . ?
C21 C1 C12 C11 0.42(18) . . . . ?
C21 C3 C4 C5 -179.04(10) . . . . ?
C21 C3 C4 C11 0.27(17) . . . . ?
C3 C4 C5 C6 179.17(10) . . . . ?
C3 C4 C5 C17 -0.77(17) . . . . ?
C3 C4 C11 C12 0.28(16) . . . . ?
C3 C4 C11 C13 -179.23(10) . . . . ?
C4 C5 C6 C7 -178.55(9) . . . . ?
C4 C5 C6 C15 0.21(16) . . . . ?
C4 C5 C17 N2 178.64(10) . . . . ?
C4 C11 C12 C1 -0.64(17) . . . . ?
C4 C11 C13 C14 178.14(10) . . . . ?
C4 C11 C13 C15 -0.14(17) . . . . ?
C5 C4 C11 C12 179.61(10) . . . . ?
C5 C4 C11 C13 0.10(16) . . . . ?
C5 C6 C7 C8 178.74(10) . . . . ?
C5 C6 C7 C16 -0.11(16) . . . . ?
C5 C6 C15 C13 -0.24(16) . . . . ?
C6 C5 C17 N2 -1.29(17) . . . . ?
C6 C7 C8 C9 -177.86(10) . . . . ?
C6 C7 C16 N2 -1.46(17) . . . . ?
C6 C7 C16 C18 178.16(10) . . . . ?
C7 C6 C15 C13 178.47(10) . . . . ?
C7 C8 C9 C10 -0.32(18) . . . . ?
C7 C16 C18 C10 -0.15(18) . . . . ?
C8 C7 C16 N2 179.63(10) . . . . ?
C8 C7 C16 C18 -0.75(17) . . . . ?
C8 C9 C10 C18 -0.60(19) . . . . ?
C9 C10 C18 C16 0.83(18) . . . . ?
C11 C4 C5 C6 -0.14(16) . . . . ?
C11 C4 C5 C17 179.92(9) . . . . ?
C11 C13 C15 C6 0.21(17) . . . . ?
C12 C1 C21 F1 -179.99(10) . . . . ?
C12 C1 C21 C3 0.16(18) . . . . ?
C12 C11 C13 C14 -1.36(17) . . . . ?
C12 C11 C13 C15 -179.64(10) . . . . ?
C13 C11 C12 C1 178.86(10) . . . . ?
C14 C13 C15 C6 -178.07(10) . . . . ?
C15 C6 C7 C8 0.02(17) . . . . ?
C15 C6 C7 C16 -178.83(10) . . . . ?
C16 N2 C17 C5 -0.22(17) . . . . ?
C16 C7 C8 C9 0.98(17) . . . . ?
C17 N2 C16 C7 1.64(17) . . . . ?
C17 N2 C16 C18 -178.00(10) . . . . ?
C17 C5 C6 C7 1.38(15) . . . . ?
C17 C5 C6 C15 -179.85(9) . . . . ?

_platon_squeeze_details          ?
_platon_squeeze_special_details  ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.084 0.000 0.500 85 23 '2.4 H2O'

_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'
