# 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_d-cn-bifph
_database_code_depnum_ccdc_archive 'CCDC 2240226'
loop_
_audit_author_name
_audit_author_address
'Cheng Liu'
;Jilin University
China
;
_audit_update_record             
;
2023-02-06 deposited with the CCDC.	2023-11-30 downloaded from the CCDC.
;
_audit_creation_date             2023-02-06
_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         '2(C16 H10 F N3)'
_chemical_formula_sum            'C32 H20 F2 N6'
_chemical_formula_weight         526.54
_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                   23.6834(9)
_cell_length_b                   12.4341(5)
_cell_length_c                   21.9726(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.0540(10)
_cell_angle_gamma                90
_cell_volume                     6406.7(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9890
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      29.27
_cell_measurement_theta_min      3.08
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.990
_exptl_absorpt_coefficient_mu    0.075
_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    1.092
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2176
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0873
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            85460
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.582
_diffrn_reflns_theta_min         2.547
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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                5368
_reflns_number_total             8977
_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  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         8977
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1007
_refine_ls_R_factor_gt           0.0512
_refine_ls_restrained_S_all      1.001
_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)+(0.0659P)²+4.6337P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1211
_refine_ls_wR_factor_ref         0.1531
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C22(H22)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C8(H8), C9(H9), C12(H12), C13(H13), C15(H15),
 C16(H16), C17(H17), C18(H18), C24(H24), C25(H25), C28(H28), C29(H29), C31(H31),
  C32(H32)
;
_atom_sites_solution_hydrogens   mixed
_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 0.87245(5) 0.35851(10) 0.26177(6) 0.0537(3) Uani 1 1 d . . . . .
F2 F 0.78466(5) 0.92373(9) 0.22875(5) 0.0405(3) Uani 1 1 d . . . . .
N1 N 0.84522(6) 0.16650(11) 0.62486(6) 0.0285(3) Uani 1 1 d . . . . .
H1 H 0.8399 0.0966 0.6213 0.034 Uiso 1 1 calc R U . . .
N2 N 0.83962(6) 0.34176(11) 0.60023(7) 0.0304(3) Uani 1 1 d . . . . .
N3 N 0.84671(7) 0.06032(12) 0.47515(7) 0.0346(3) Uani 1 1 d . . . . .
N4 N 0.86667(6) 0.65969(11) 0.48786(7) 0.0288(3) Uani 1 1 d . . . . .
N5 N 0.88373(6) 0.83589(12) 0.47785(7) 0.0312(3) Uani 1 1 d . . . . .
N6 N 0.80928(7) 0.93882(12) 0.59862(7) 0.0365(4) Uani 1 1 d . . . . .
C1 C 0.93158(8) 0.2623(2) 0.76849(9) 0.0473(5) Uani 1 1 d . . . . .
H1A H 0.9526 0.2412 0.8066 0.057 Uiso 1 1 calc R U . . .
C2 C 0.90580(8) 0.18353(18) 0.72918(8) 0.0409(5) Uani 1 1 d . . . . .
H2 H 0.9088 0.1092 0.7391 0.049 Uiso 1 1 calc R U . . .
C3 C 0.87517(7) 0.22037(15) 0.67416(8) 0.0316(4) Uani 1 1 d . . . . .
C4 C 0.82541(7) 0.24335(13) 0.58275(7) 0.0254(3) Uani 1 1 d . . . . .
C5 C 0.79120(7) 0.21463(12) 0.52199(7) 0.0244(3) Uani 1 1 d . . . . .
C6 C 0.77461(7) 0.31419(12) 0.47894(7) 0.0252(3) Uani 1 1 d . . . . .
H6 H 0.7833 0.3815 0.5034 0.030 Uiso 1 1 calc R U . . .
C7 C 0.87117(7) 0.32929(15) 0.65844(8) 0.0324(4) Uani 1 1 d . . . . .
C8 C 0.89755(8) 0.40723(17) 0.69911(10) 0.0427(5) Uani 1 1 d . . . . .
H8 H 0.8948 0.4817 0.6894 0.051 Uiso 1 1 calc R U . . .
C9 C 0.92764(8) 0.3713(2) 0.75378(10) 0.0480(5) Uani 1 1 d . . . . .
H9 H 0.9461 0.4222 0.7821 0.058 Uiso 1 1 calc R U . . .
C10 C 0.82202(7) 0.12862(13) 0.49475(7) 0.0271(3) Uani 1 1 d . . . . .
C11 C 0.79858(7) 0.32461(13) 0.41935(8) 0.0268(3) Uani 1 1 d . . . . .
C12 C 0.79322(7) 0.24402(13) 0.37471(8) 0.0282(3) Uani 1 1 d . . . . .
H12 H 0.7723 0.1807 0.3808 0.034 Uiso 1 1 calc R U . . .
C13 C 0.81802(8) 0.25518(15) 0.32152(8) 0.0340(4) Uani 1 1 d . . . . .
H13 H 0.8148 0.1999 0.2914 0.041 Uiso 1 1 calc R U . . .
C14 C 0.84750(8) 0.34855(16) 0.31349(9) 0.0392(4) Uani 1 1 d . . . . .
C15 C 0.85283(8) 0.43065(15) 0.35547(9) 0.0411(5) Uani 1 1 d . . . . .
H15 H 0.8727 0.4947 0.3481 0.049 Uiso 1 1 calc R U . . .
C16 C 0.82850(8) 0.41820(14) 0.40893(9) 0.0342(4) Uani 1 1 d . . . . .
H16 H 0.8322 0.4739 0.4388 0.041 Uiso 1 1 calc R U . . .
C17 C 1.00838(8) 0.63424(16) 0.43340(9) 0.0385(4) Uani 1 1 d . . . . .
H17 H 1.0362 0.5840 0.4242 0.046 Uiso 1 1 calc R U . . .
C18 C 0.95859(8) 0.59678(15) 0.45242(8) 0.0351(4) Uani 1 1 d . . . . .
H18 H 0.9517 0.5220 0.4561 0.042 Uiso 1 1 calc R U . . .
C19 C 0.91890(7) 0.67345(14) 0.46599(8) 0.0292(4) Uani 1 1 d . . . . .
C20 C 0.84807(7) 0.75783(13) 0.49417(8) 0.0279(3) Uani 1 1 d . . . . .
C21 C 0.79258(7) 0.78562(12) 0.51648(8) 0.0262(3) Uani 1 1 d . . . . .
C22 C 0.74025(7) 0.81670(12) 0.46569(7) 0.0259(3) Uani 1 1 d . . . . .
H22 H 0.7212 0.8814 0.4806 0.031 Uiso 1 1 calc R U . . .
C23 C 0.92993(7) 0.78348(14) 0.45943(8) 0.0313(4) Uani 1 1 d . . . . .
C24 C 0.97993(8) 0.82142(16) 0.44000(9) 0.0378(4) Uani 1 1 d . . . . .
H24 H 0.9870 0.8961 0.4356 0.045 Uiso 1 1 calc R U . . .
C25 C 1.01864(8) 0.74402(17) 0.42750(9) 0.0403(4) Uani 1 1 d . . . . .
H25 H 1.0534 0.7663 0.4145 0.048 Uiso 1 1 calc R U . . .
C26 C 0.80233(7) 0.86993(13) 0.56373(8) 0.0286(4) Uani 1 1 d . . . . .
C27 C 0.75070(7) 0.83811(13) 0.40087(8) 0.0270(3) Uani 1 1 d . . . . .
C28 C 0.73256(7) 0.93689(13) 0.37518(8) 0.0291(4) Uani 1 1 d . . . . .
H28 H 0.7124 0.9852 0.3978 0.035 Uiso 1 1 calc R U . . .
C29 C 0.74359(8) 0.96552(14) 0.31693(8) 0.0324(4) Uani 1 1 d . . . . .
H29 H 0.7312 1.0328 0.2995 0.039 Uiso 1 1 calc R U . . .
C30 C 0.77279(8) 0.89440(14) 0.28511(8) 0.0315(4) Uani 1 1 d . . . . .
C31 C 0.79022(7) 0.79484(14) 0.30826(8) 0.0316(4) Uani 1 1 d . . . . .
H31 H 0.8096 0.7465 0.2848 0.038 Uiso 1 1 calc R U . . .
C32 C 0.77894(7) 0.76671(13) 0.36626(8) 0.0296(4) Uani 1 1 d . . . . .
H32 H 0.7905 0.6983 0.3827 0.036 Uiso 1 1 calc R U . . .
H5 H 0.8765(9) 0.9073(18) 0.4770(9) 0.044(6) Uiso 1 1 d . . . . .


_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 1.358(2) . ?
F2 C30 1.3575(18) . ?
N1 H1 0.8800 . ?
N1 C3 1.382(2) . ?
N1 C4 1.367(2) . ?
N2 C4 1.312(2) . ?
N2 C7 1.396(2) . ?
N3 C10 1.149(2) . ?
N4 C19 1.399(2) . ?
N4 C20 1.311(2) . ?
N5 C20 1.367(2) . ?
N5 C23 1.382(2) . ?
N5 H5 0.90(2) . ?
N6 C26 1.146(2) . ?
C1 H1A 0.9500 . ?
C1 C2 1.390(3) . ?
C1 C9 1.393(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.397(3) . ?
C3 C7 1.398(3) . ?
C4 C5 1.504(2) . ?
C5 C6 1.574(2) . ?
C5 C6 1.597(2) 7_656 ?
C5 C10 1.469(2) . ?
C6 C5 1.597(2) 7_656 ?
C6 H6 1.0000 . ?
C6 C11 1.504(2) . ?
C7 C8 1.404(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.382(3) . ?
C9 H9 0.9500 . ?
C11 C12 1.395(2) . ?
C11 C16 1.398(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.379(3) . ?
C14 C15 1.370(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.388(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C17 C18 1.386(3) . ?
C17 C25 1.396(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.400(2) . ?
C19 C23 1.404(2) . ?
C20 C21 1.506(2) . ?
C21 C22 1.569(2) 7_666 ?
C21 C22 1.595(2) . ?
C21 C26 1.471(2) . ?
C22 C21 1.569(2) 7_666 ?
C22 H22 1.0000 . ?
C22 C27 1.503(2) . ?
C23 C24 1.396(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.383(3) . ?
C25 H25 0.9500 . ?
C27 C28 1.394(2) . ?
C27 C32 1.399(2) . ?
C28 H28 0.9500 . ?
C28 C29 1.388(2) . ?
C29 H29 0.9500 . ?
C29 C30 1.373(2) . ?
C30 C31 1.379(2) . ?
C31 H31 0.9500 . ?
C31 C32 1.383(2) . ?
C32 H32 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
C3 N1 H1 126.8 . . ?
C4 N1 H1 126.8 . . ?
C4 N1 C3 106.36(14) . . ?
C4 N2 C7 104.29(14) . . ?
C20 N4 C19 104.40(14) . . ?
C20 N5 C23 106.59(14) . . ?
C20 N5 H5 125.5(13) . . ?
C23 N5 H5 127.8(13) . . ?
C2 C1 H1A 118.9 . . ?
C2 C1 C9 122.2(2) . . ?
C9 C1 H1A 118.9 . . ?
C1 C2 H2 122.1 . . ?
C1 C2 C3 115.9(2) . . ?
C3 C2 H2 122.1 . . ?
N1 C3 C2 131.81(18) . . ?
N1 C3 C7 105.44(15) . . ?
C2 C3 C7 122.73(17) . . ?
N1 C4 C5 121.73(14) . . ?
N2 C4 N1 113.84(15) . . ?
N2 C4 C5 124.42(15) . . ?
C4 C5 C6 117.91(12) . 7_656 ?
C4 C5 C6 113.87(13) . . ?
C6 C5 C6 90.44(11) . 7_656 ?
C10 C5 C4 107.33(13) . . ?
C10 C5 C6 111.80(13) . 7_656 ?
C10 C5 C6 115.11(13) . . ?
C5 C6 C5 89.56(11) . 7_656 ?
C5 C6 H6 108.7 7_656 . ?
C5 C6 H6 108.7 . . ?
C11 C6 C5 119.68(14) . 7_656 ?
C11 C6 C5 119.87(13) . . ?
C11 C6 H6 108.7 . . ?
N2 C7 C3 110.07(15) . . ?
N2 C7 C8 129.75(18) . . ?
C3 C7 C8 120.18(18) . . ?
C7 C8 H8 121.3 . . ?
C9 C8 C7 117.3(2) . . ?
C9 C8 H8 121.3 . . ?
C1 C9 H9 119.1 . . ?
C8 C9 C1 121.71(19) . . ?
C8 C9 H9 119.1 . . ?
N3 C10 C5 177.99(18) . . ?
C12 C11 C6 122.81(14) . . ?
C12 C11 C16 118.74(15) . . ?
C16 C11 C6 118.44(15) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.86(16) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 120.8 . . ?
C14 C13 C12 118.30(17) . . ?
C14 C13 H13 120.8 . . ?
F1 C14 C13 118.13(18) . . ?
F1 C14 C15 119.06(17) . . ?
C15 C14 C13 122.81(16) . . ?
C14 C15 H15 120.8 . . ?
C14 C15 C16 118.49(17) . . ?
C16 C15 H15 120.8 . . ?
C11 C16 H16 119.6 . . ?
C15 C16 C11 120.78(17) . . ?
C15 C16 H16 119.6 . . ?
C18 C17 H17 119.2 . . ?
C18 C17 C25 121.56(17) . . ?
C25 C17 H17 119.2 . . ?
C17 C18 H18 121.3 . . ?
C17 C18 C19 117.42(17) . . ?
C19 C18 H18 121.3 . . ?
N4 C19 C18 129.96(16) . . ?
N4 C19 C23 109.92(14) . . ?
C18 C19 C23 120.10(15) . . ?
N4 C20 N5 113.83(14) . . ?
N4 C20 C21 124.71(14) . . ?
N5 C20 C21 121.46(14) . . ?
C20 C21 C22 112.38(13) . 7_666 ?
C20 C21 C22 117.13(13) . . ?
C22 C21 C22 90.43(12) 7_666 . ?
C26 C21 C20 109.61(14) . . ?
C26 C21 C22 115.84(13) . 7_666 ?
C26 C21 C22 110.55(13) . . ?
C21 C22 C21 89.57(12) 7_666 . ?
C21 C22 H22 108.0 7_666 . ?
C21 C22 H22 108.0 . . ?
C27 C22 C21 119.40(13) . . ?
C27 C22 C21 122.24(14) . 7_666 ?
C27 C22 H22 108.0 . . ?
N5 C23 C19 105.26(14) . . ?
N5 C23 C24 132.11(17) . . ?
C24 C23 C19 122.60(16) . . ?
C23 C24 H24 122.0 . . ?
C25 C24 C23 116.10(18) . . ?
C25 C24 H24 122.0 . . ?
C17 C25 H25 118.9 . . ?
C24 C25 C17 122.22(17) . . ?
C24 C25 H25 118.9 . . ?
N6 C26 C21 177.08(19) . . ?
C28 C27 C22 117.22(14) . . ?
C28 C27 C32 118.86(15) . . ?
C32 C27 C22 123.89(14) . . ?
C27 C28 H28 119.6 . . ?
C29 C28 C27 120.81(15) . . ?
C29 C28 H28 119.6 . . ?
C28 C29 H29 120.7 . . ?
C30 C29 C28 118.54(16) . . ?
C30 C29 H29 120.7 . . ?
F2 C30 C29 118.36(15) . . ?
F2 C30 C31 119.21(15) . . ?
C29 C30 C31 122.43(15) . . ?
C30 C31 H31 120.6 . . ?
C30 C31 C32 118.71(15) . . ?
C32 C31 H31 120.6 . . ?
C27 C32 H32 119.7 . . ?
C31 C32 C27 120.62(15) . . ?
C31 C32 H32 119.7 . . ?

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 C14 C15 C16 -178.21(17) . . . . ?
F2 C30 C31 C32 178.66(16) . . . . ?
N1 C3 C7 N2 -0.44(18) . . . . ?
N1 C3 C7 C8 -179.81(15) . . . . ?
N1 C4 C5 C6 78.29(18) . . . 7_656 ?
N1 C4 C5 C6 -177.59(13) . . . . ?
N1 C4 C5 C10 -48.97(19) . . . . ?
N2 C4 C5 C6 1.6(2) . . . . ?
N2 C4 C5 C6 -102.55(18) . . . 7_656 ?
N2 C4 C5 C10 130.19(16) . . . . ?
N2 C7 C8 C9 -178.33(17) . . . . ?
N4 C19 C23 N5 0.2(2) . . . . ?
N4 C19 C23 C24 178.15(17) . . . . ?
N4 C20 C21 C22 2.4(2) . . . 7_666 ?
N4 C20 C21 C22 -100.35(19) . . . . ?
N4 C20 C21 C26 132.69(18) . . . . ?
N5 C20 C21 C22 79.0(2) . . . . ?
N5 C20 C21 C22 -178.33(15) . . . 7_666 ?
N5 C20 C21 C26 -48.0(2) . . . . ?
N5 C23 C24 C25 177.18(19) . . . . ?
C1 C2 C3 N1 179.16(17) . . . . ?
C1 C2 C3 C7 1.1(2) . . . . ?
C2 C1 C9 C8 0.2(3) . . . . ?
C2 C3 C7 N2 178.03(15) . . . . ?
C2 C3 C7 C8 -1.3(3) . . . . ?
C3 N1 C4 N2 -0.14(18) . . . . ?
C3 N1 C4 C5 179.10(13) . . . . ?
C3 C7 C8 C9 0.9(3) . . . . ?
C4 N1 C3 C2 -177.93(17) . . . . ?
C4 N1 C3 C7 0.34(17) . . . . ?
C4 N2 C7 C3 0.35(18) . . . . ?
C4 N2 C7 C8 179.65(17) . . . . ?
C4 C5 C6 C5 -121.01(15) . . . 7_656 ?
C4 C5 C6 C11 114.48(16) . . . . ?
C5 C6 C11 C12 -53.8(2) 7_656 . . . ?
C5 C6 C11 C12 54.6(2) . . . . ?
C5 C6 C11 C16 127.53(16) 7_656 . . . ?
C5 C6 C11 C16 -123.99(17) . . . . ?
C6 C5 C6 C5 0.004(0) 7_656 . . 7_656 ?
C6 C5 C6 C11 -124.50(17) 7_656 . . . ?
C6 C11 C12 C13 -177.31(16) . . . . ?
C6 C11 C16 C15 178.22(17) . . . . ?
C7 N2 C4 N1 -0.12(18) . . . . ?
C7 N2 C4 C5 -179.35(14) . . . . ?
C7 C8 C9 C1 -0.4(3) . . . . ?
C9 C1 C2 C3 -0.6(3) . . . . ?
C10 C5 C6 C5 114.44(16) . . . 7_656 ?
C10 C5 C6 C11 -10.1(2) . . . . ?
C11 C12 C13 C14 -0.8(3) . . . . ?
C12 C11 C16 C15 -0.5(3) . . . . ?
C12 C13 C14 F1 179.04(16) . . . . ?
C12 C13 C14 C15 -0.6(3) . . . . ?
C13 C14 C15 C16 1.4(3) . . . . ?
C14 C15 C16 C11 -0.8(3) . . . . ?
C16 C11 C12 C13 1.3(3) . . . . ?
C17 C18 C19 N4 -177.56(18) . . . . ?
C17 C18 C19 C23 0.8(3) . . . . ?
C18 C17 C25 C24 -0.2(3) . . . . ?
C18 C19 C23 N5 -178.44(16) . . . . ?
C18 C19 C23 C24 -0.5(3) . . . . ?
C19 N4 C20 N5 0.4(2) . . . . ?
C19 N4 C20 C21 179.71(16) . . . . ?
C19 C23 C24 C25 -0.1(3) . . . . ?
C20 N4 C19 C18 178.13(19) . . . . ?
C20 N4 C19 C23 -0.3(2) . . . . ?
C20 N5 C23 C19 0.01(19) . . . . ?
C20 N5 C23 C24 -177.7(2) . . . . ?
C20 C21 C22 C21 115.57(16) . . . 7_666 ?
C20 C21 C22 C27 -11.9(2) . . . . ?
C21 C22 C27 C28 125.43(17) 7_666 . . . ?
C21 C22 C27 C28 -124.38(16) . . . . ?
C21 C22 C27 C32 53.4(2) . . . . ?
C21 C22 C27 C32 -56.8(2) 7_666 . . . ?
C22 C21 C22 C21 0.000(1) 7_666 . . 7_666 ?
C22 C21 C22 C27 -127.45(16) 7_666 . . . ?
C22 C27 C28 C29 176.18(16) . . . . ?
C22 C27 C32 C31 -175.85(16) . . . . ?
C23 N5 C20 N4 -0.2(2) . . . . ?
C23 N5 C20 C21 -179.61(15) . . . . ?
C23 C24 C25 C17 0.5(3) . . . . ?
C25 C17 C18 C19 -0.4(3) . . . . ?
C26 C21 C22 C21 -117.93(15) . . . 7_666 ?
C26 C21 C22 C27 114.62(15) . . . . ?
C27 C28 C29 C30 0.0(3) . . . . ?
C28 C27 C32 C31 1.9(3) . . . . ?
C28 C29 C30 F2 -178.49(15) . . . . ?
C28 C29 C30 C31 1.7(3) . . . . ?
C29 C30 C31 C32 -1.5(3) . . . . ?
C30 C31 C32 C27 -0.4(3) . . . . ?
C32 C27 C28 C29 -1.7(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.174 0.250 439.2 95.1 '2 C6H12'
2 0.000 -0.174 0.750 439.2 95.1 '2 C6H12'
3 0.500 0.326 0.750 439.2 95.1 '2 C6H12'
4 0.500 0.674 0.250 439.2 95.1 '2 C6H12'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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_e-cn-bifph-or
_database_code_depnum_ccdc_archive 'CCDC 2240230'
loop_
_audit_author_name
_audit_author_address
'Cheng Liu'
;Jilin University
China
;
_audit_update_record             
;
2023-03-27 deposited with the CCDC.	2023-11-30 downloaded from the CCDC.
;
_audit_creation_date             2023-03-27
_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         'C16 H10 F N3'
_chemical_formula_sum            'C16 H10 F N3'
_chemical_formula_weight         263.27
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.7580(3)
_cell_length_b                   28.3322(12)
_cell_length_c                   7.3254(3)
_cell_angle_alpha                90
_cell_angle_beta                 116.4820(10)
_cell_angle_gamma                90
_cell_volume                     1255.42(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9974
_cell_measurement_temperature    300.0
_cell_measurement_theta_max      29.401
_cell_measurement_theta_min      2.876
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.096
_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 orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            36758
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.689
_diffrn_reflns_theta_min         2.876
_diffrn_ambient_temperature      300.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_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                2387
_reflns_number_total             3551
_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    ?
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3551
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0604
_refine_ls_restrained_S_all      1.049
_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)+(0.0585P)²+0.6321P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1670
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C3(H3A), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15)
;
_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 0.6972(3) 0.72219(5) 0.3458(3) 0.0938(6) Uani 1 1 d . . . . .
N2 N 0.6597(3) 0.40576(5) 0.2401(3) 0.0459(4) Uani 1 1 d . . . . .
N3 N 0.3310(2) 0.43234(5) 0.2019(2) 0.0416(4) Uani 1 1 d . . . . .
H3 H 0.2302 0.4520 0.1931 0.050 Uiso 1 1 calc R U . . .
N4 N 0.9942(3) 0.49586(7) 0.2341(3) 0.0594(5) Uani 1 1 d . . . . .
C1 C 0.6561(4) 0.67521(8) 0.3295(4) 0.0605(6) Uani 1 1 d . . . . .
C2 C 0.4482(4) 0.65994(8) 0.2868(4) 0.0637(6) Uani 1 1 d . . . . .
H2 H 0.3363 0.6813 0.2685 0.076 Uiso 1 1 calc R U . . .
C3 C 0.4090(3) 0.61212(7) 0.2716(3) 0.0518(5) Uani 1 1 d . . . . .
H3A H 0.2689 0.6011 0.2443 0.062 Uiso 1 1 calc R U . . .
C4 C 0.5748(3) 0.57975(6) 0.2961(3) 0.0422(4) Uani 1 1 d . . . . .
C5 C 0.5162(3) 0.53011(6) 0.2761(3) 0.0423(4) Uani 1 1 d . . . . .
H5 H 0.3815 0.5236 0.2765 0.051 Uiso 1 1 calc R U . . .
C6 C 0.6238(3) 0.49186(6) 0.2569(3) 0.0398(4) Uani 1 1 d . . . . .
C7 C 0.5408(3) 0.44310(6) 0.2343(3) 0.0390(4) Uani 1 1 d . . . . .
C8 C 0.5176(3) 0.36772(7) 0.2100(3) 0.0452(4) Uani 1 1 d . . . . .
C9 C 0.5533(4) 0.31939(8) 0.2017(4) 0.0603(6) Uani 1 1 d . . . . .
H9 H 0.6894 0.3078 0.2191 0.072 Uiso 1 1 calc R U . . .
C10 C 0.3802(5) 0.28969(8) 0.1669(4) 0.0691(7) Uani 1 1 d . . . . .
H10 H 0.3995 0.2574 0.1590 0.083 Uiso 1 1 calc R U . . .
C11 C 0.7847(3) 0.59729(7) 0.3418(4) 0.0527(5) Uani 1 1 d . . . . .
H11 H 0.8989 0.5764 0.3622 0.063 Uiso 1 1 calc R U . . .
C12 C 0.8248(4) 0.64491(8) 0.3570(4) 0.0597(6) Uani 1 1 d . . . . .
H12 H 0.9644 0.6564 0.3855 0.072 Uiso 1 1 calc R U . . .
C13 C 0.3114(3) 0.38390(7) 0.1860(3) 0.0430(4) Uani 1 1 d . . . . .
C14 C 0.1757(4) 0.30640(8) 0.1431(4) 0.0677(7) Uani 1 1 d . . . . .
H14 H 0.0628 0.2849 0.1200 0.081 Uiso 1 1 calc R U . . .
C15 C 0.1367(4) 0.35371(8) 0.1529(4) 0.0560(5) Uani 1 1 d . . . . .
H15 H 0.0010 0.3649 0.1382 0.067 Uiso 1 1 calc R U . . .
C16 C 0.8325(3) 0.49435(6) 0.2470(3) 0.0432(4) Uani 1 1 d . . . . .


_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 1.354(3) . ?
N2 C7 1.318(2) . ?
N2 C8 1.394(2) . ?
N3 H3 0.8600 . ?
N3 C7 1.364(2) . ?
N3 C13 1.379(2) . ?
N4 C16 1.138(2) . ?
C1 C2 1.366(3) . ?
C1 C12 1.369(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.375(3) . ?
C3 H3A 0.9300 . ?
C3 C4 1.396(3) . ?
C4 C5 1.451(3) . ?
C4 C11 1.396(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.347(2) . ?
C6 C7 1.472(2) . ?
C6 C16 1.446(2) . ?
C8 C9 1.396(3) . ?
C8 C13 1.402(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.370(3) . ?
C10 H10 0.9300 . ?
C10 C14 1.397(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.371(3) . ?
C12 H12 0.9300 . ?
C13 C15 1.389(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.374(3) . ?
C15 H15 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 N2 C8 104.38(15) . . ?
C7 N3 H3 126.6 . . ?
C7 N3 C13 106.87(14) . . ?
C13 N3 H3 126.6 . . ?
F1 C1 C2 118.7(2) . . ?
F1 C1 C12 118.6(2) . . ?
C2 C1 C12 122.6(2) . . ?
C1 C2 H2 120.9 . . ?
C1 C2 C3 118.1(2) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3A 119.3 . . ?
C2 C3 C4 121.5(2) . . ?
C4 C3 H3A 119.3 . . ?
C3 C4 C5 117.17(17) . . ?
C11 C4 C3 117.94(18) . . ?
C11 C4 C5 124.89(17) . . ?
C4 C5 H5 114.6 . . ?
C6 C5 C4 130.90(17) . . ?
C6 C5 H5 114.6 . . ?
C5 C6 C7 124.75(16) . . ?
C5 C6 C16 123.38(17) . . ?
C16 C6 C7 111.81(15) . . ?
N2 C7 N3 113.46(16) . . ?
N2 C7 C6 123.59(16) . . ?
N3 C7 C6 122.95(15) . . ?
N2 C8 C9 130.17(18) . . ?
N2 C8 C13 110.08(16) . . ?
C9 C8 C13 119.76(18) . . ?
C8 C9 H9 121.3 . . ?
C10 C9 C8 117.5(2) . . ?
C10 C9 H9 121.3 . . ?
C9 C10 H10 119.0 . . ?
C9 C10 C14 122.0(2) . . ?
C14 C10 H10 119.0 . . ?
C4 C11 H11 119.6 . . ?
C12 C11 C4 120.87(19) . . ?
C12 C11 H11 119.6 . . ?
C1 C12 C11 118.9(2) . . ?
C1 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
N3 C13 C8 105.21(15) . . ?
N3 C13 C15 132.05(18) . . ?
C15 C13 C8 122.74(18) . . ?
C10 C14 H14 119.1 . . ?
C15 C14 C10 121.8(2) . . ?
C15 C14 H14 119.1 . . ?
C13 C15 H15 121.9 . . ?
C14 C15 C13 116.2(2) . . ?
C14 C15 H15 121.9 . . ?
N4 C16 C6 178.2(2) . . ?

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 -179.7(2) . . . . ?
F1 C1 C12 C11 179.6(2) . . . . ?
N2 C8 C9 C10 -179.2(2) . . . . ?
N2 C8 C13 N3 0.1(2) . . . . ?
N2 C8 C13 C15 179.79(19) . . . . ?
N3 C13 C15 C14 179.2(2) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
C2 C1 C12 C11 -0.2(4) . . . . ?
C2 C3 C4 C5 -179.7(2) . . . . ?
C2 C3 C4 C11 1.5(3) . . . . ?
C3 C4 C5 C6 167.2(2) . . . . ?
C3 C4 C11 C12 -1.6(3) . . . . ?
C4 C5 C6 C7 -178.93(19) . . . . ?
C4 C5 C6 C16 -1.8(3) . . . . ?
C4 C11 C12 C1 0.9(4) . . . . ?
C5 C4 C11 C12 179.7(2) . . . . ?
C5 C6 C7 N2 -171.62(19) . . . . ?
C5 C6 C7 N3 9.5(3) . . . . ?
C7 N2 C8 C9 -179.9(2) . . . . ?
C7 N2 C8 C13 0.1(2) . . . . ?
C7 N3 C13 C8 -0.2(2) . . . . ?
C7 N3 C13 C15 -179.9(2) . . . . ?
C8 N2 C7 N3 -0.2(2) . . . . ?
C8 N2 C7 C6 -179.20(17) . . . . ?
C8 C9 C10 C14 -0.9(4) . . . . ?
C8 C13 C15 C14 -0.5(3) . . . . ?
C9 C8 C13 N3 180.00(19) . . . . ?
C9 C8 C13 C15 -0.3(3) . . . . ?
C9 C10 C14 C15 0.1(4) . . . . ?
C10 C14 C15 C13 0.5(4) . . . . ?
C11 C4 C5 C6 -14.1(3) . . . . ?
C12 C1 C2 C3 0.1(4) . . . . ?
C13 N3 C7 N2 0.2(2) . . . . ?
C13 N3 C7 C6 179.26(17) . . . . ?
C13 C8 C9 C10 0.9(3) . . . . ?
C16 C6 C7 N2 11.0(3) . . . . ?
C16 C6 C7 N3 -167.93(17) . . . . ?

_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_e-cn-bifph-g
_database_code_depnum_ccdc_archive 'CCDC 2240229'
loop_
_audit_author_name
_audit_author_address
'Cheng Liu'
;Jilin University
China
;
_audit_update_record             
;
2023-02-06 deposited with the CCDC.	2023-11-30 downloaded from the CCDC.
;
_audit_creation_date             2023-02-06
_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         'C16 H10 F N3'
_chemical_formula_sum            'C16 H10 F N3'
_chemical_formula_weight         263.27
_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      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                   12.8656(5)
_cell_length_b                   6.7384(3)
_cell_length_c                   28.4952(12)
_cell_angle_alpha                90
_cell_angle_beta                 99.610(2)
_cell_angle_gamma                90
_cell_volume                     2435.68(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9958
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.40
_cell_measurement_theta_min      2.90
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.099
_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    1.436
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            33077
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.505
_diffrn_reflns_theta_min         2.900
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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                2920
_reflns_number_total             3720
_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         0.361
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3720
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0471
_refine_ls_restrained_S_all      1.036
_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)+(0.0717P)²+2.2425P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1390
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C6(H6), C8(H8), C9(H9), C12(H12), C13(H13), C15(H15),
  C16(H16)
;
_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 0.63182(8) 0.58840(14) 0.49671(3) 0.0309(2) Uani 1 1 d . . . . .
N1 N 0.61879(8) 0.89065(16) 0.78572(4) 0.0153(2) Uani 1 1 d . . . . .
H1 H 0.6128 0.9890 0.7651 0.018 Uiso 1 1 calc R U . . .
N2 N 0.63671(8) 0.57805(16) 0.81413(4) 0.0159(2) Uani 1 1 d . . . . .
N3 N 0.61217(10) 0.23463(18) 0.72310(4) 0.0221(3) Uani 1 1 d . . . . .
C1 C 0.61216(11) 1.0273(2) 0.91128(5) 0.0203(3) Uani 1 1 d . . . . .
H1A H 0.6053 1.1334 0.9325 0.024 Uiso 1 1 calc R U . . .
C2 C 0.60956(10) 1.0684(2) 0.86338(5) 0.0179(3) Uani 1 1 d . . . . .
H2 H 0.6013 1.1997 0.8512 0.022 Uiso 1 1 calc R U . . .
C3 C 0.61973(10) 0.90522(19) 0.83418(4) 0.0151(2) Uani 1 1 d . . . . .
C4 C 0.62894(9) 0.69331(18) 0.77603(4) 0.0146(2) Uani 1 1 d . . . . .
C5 C 0.62805(10) 0.61700(19) 0.72774(4) 0.0149(2) Uani 1 1 d . . . . .
C6 C 0.63479(10) 0.73461(19) 0.68962(4) 0.0156(2) Uani 1 1 d . . . . .
H6 H 0.6427 0.8721 0.6968 0.019 Uiso 1 1 calc R U . . .
C7 C 0.63194(10) 0.68521(19) 0.63961(4) 0.0152(2) Uani 1 1 d . . . . .
C8 C 0.61236(10) 0.4951(2) 0.61976(5) 0.0182(3) Uani 1 1 d . . . . .
H8 H 0.5995 0.3876 0.6396 0.022 Uiso 1 1 calc R U . . .
C9 C 0.61159(11) 0.4625(2) 0.57173(5) 0.0203(3) Uani 1 1 d . . . . .
H9 H 0.5981 0.3341 0.5583 0.024 Uiso 1 1 calc R U . . .
C10 C 0.63093(11) 0.6218(2) 0.54367(5) 0.0207(3) Uani 1 1 d . . . . .
C11 C 0.63145(10) 0.70919(19) 0.85140(4) 0.0151(2) Uani 1 1 d . . . . .
C12 C 0.63457(10) 0.6713(2) 0.89994(5) 0.0176(3) Uani 1 1 d . . . . .
H12 H 0.6431 0.5403 0.9123 0.021 Uiso 1 1 calc R U . . .
C13 C 0.62468(11) 0.8319(2) 0.92935(5) 0.0202(3) Uani 1 1 d . . . . .
H13 H 0.6264 0.8100 0.9624 0.024 Uiso 1 1 calc R U . . .
C14 C 0.61918(10) 0.40456(19) 0.72477(4) 0.0165(2) Uani 1 1 d . . . . .
C15 C 0.64988(10) 0.84186(19) 0.60951(5) 0.0173(2) Uani 1 1 d . . . . .
H15 H 0.6623 0.9715 0.6224 0.021 Uiso 1 1 calc R U . . .
C16 C 0.64990(11) 0.8111(2) 0.56123(5) 0.0200(3) Uani 1 1 d . . . . .
H16 H 0.6626 0.9174 0.5410 0.024 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 C10 1.3589(15) . ?
N1 H1 0.8800 . ?
N1 C3 1.3823(16) . ?
N1 C4 1.3688(16) . ?
N2 C4 1.3251(16) . ?
N2 C11 1.3920(16) . ?
N3 C14 1.1490(17) . ?
C1 H1A 0.9500 . ?
C1 C2 1.3875(19) . ?
C1 C13 1.413(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.3984(18) . ?
C3 C11 1.4084(17) . ?
C4 C5 1.4671(17) . ?
C5 C6 1.3591(17) . ?
C5 C14 1.4374(17) . ?
C6 H6 0.9500 . ?
C6 C7 1.4577(17) . ?
C7 C8 1.4059(18) . ?
C7 C15 1.4033(18) . ?
C8 H8 0.9500 . ?
C8 C9 1.3846(18) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(2) . ?
C10 C16 1.377(2) . ?
C11 C12 1.4003(17) . ?
C12 H12 0.9500 . ?
C12 C13 1.3875(19) . ?
C13 H13 0.9500 . ?
C15 H15 0.9500 . ?
C15 C16 1.3915(18) . ?
C16 H16 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
C3 N1 H1 126.7 . . ?
C4 N1 H1 126.7 . . ?
C4 N1 C3 106.58(10) . . ?
C4 N2 C11 104.27(11) . . ?
C2 C1 H1A 119.1 . . ?
C2 C1 C13 121.81(12) . . ?
C13 C1 H1A 119.1 . . ?
C1 C2 H2 122.0 . . ?
C1 C2 C3 116.04(12) . . ?
C3 C2 H2 122.0 . . ?
N1 C3 C2 131.62(12) . . ?
N1 C3 C11 105.31(10) . . ?
C2 C3 C11 123.05(12) . . ?
N1 C4 C5 122.93(11) . . ?
N2 C4 N1 113.62(11) . . ?
N2 C4 C5 123.42(12) . . ?
C6 C5 C4 123.62(12) . . ?
C6 C5 C14 123.28(12) . . ?
C14 C5 C4 113.10(11) . . ?
C5 C6 H6 114.6 . . ?
C5 C6 C7 130.81(12) . . ?
C7 C6 H6 114.6 . . ?
C8 C7 C6 125.09(11) . . ?
C15 C7 C6 116.47(11) . . ?
C15 C7 C8 118.43(12) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 120.90(12) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 H9 120.8 . . ?
C8 C9 C10 118.36(13) . . ?
C10 C9 H9 120.8 . . ?
F1 C10 C9 118.15(12) . . ?
F1 C10 C16 118.75(12) . . ?
C16 C10 C9 123.10(12) . . ?
N2 C11 C3 110.21(11) . . ?
N2 C11 C12 129.86(12) . . ?
C12 C11 C3 119.93(12) . . ?
C11 C12 H12 121.2 . . ?
C13 C12 C11 117.64(12) . . ?
C13 C12 H12 121.2 . . ?
C1 C13 H13 119.2 . . ?
C12 C13 C1 121.53(12) . . ?
C12 C13 H13 119.2 . . ?
N3 C14 C5 179.01(14) . . ?
C7 C15 H15 119.3 . . ?
C16 C15 C7 121.31(12) . . ?
C16 C15 H15 119.3 . . ?
C10 C16 C15 117.88(12) . . ?
C10 C16 H16 121.1 . . ?
C15 C16 H16 121.1 . . ?

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 C10 C16 C15 -179.26(12) . . . . ?
N1 C3 C11 N2 -0.44(14) . . . . ?
N1 C3 C11 C12 -179.53(11) . . . . ?
N1 C4 C5 C6 11.36(19) . . . . ?
N1 C4 C5 C14 -168.59(12) . . . . ?
N2 C4 C5 C6 -170.55(12) . . . . ?
N2 C4 C5 C14 9.50(17) . . . . ?
N2 C11 C12 C13 -178.23(12) . . . . ?
C1 C2 C3 N1 178.73(13) . . . . ?
C1 C2 C3 C11 0.34(19) . . . . ?
C2 C1 C13 C12 -0.3(2) . . . . ?
C2 C3 C11 N2 178.31(12) . . . . ?
C2 C3 C11 C12 -0.77(19) . . . . ?
C3 N1 C4 N2 -0.17(14) . . . . ?
C3 N1 C4 C5 178.09(11) . . . . ?
C3 C11 C12 C13 0.66(18) . . . . ?
C4 N1 C3 C2 -178.24(13) . . . . ?
C4 N1 C3 C11 0.36(13) . . . . ?
C4 N2 C11 C3 0.34(14) . . . . ?
C4 N2 C11 C12 179.31(13) . . . . ?
C4 C5 C6 C7 -177.93(12) . . . . ?
C5 C6 C7 C8 5.4(2) . . . . ?
C5 C6 C7 C15 -174.84(13) . . . . ?
C6 C7 C8 C9 -179.78(12) . . . . ?
C6 C7 C15 C16 179.41(12) . . . . ?
C7 C8 C9 C10 0.2(2) . . . . ?
C7 C15 C16 C10 0.5(2) . . . . ?
C8 C7 C15 C16 -0.86(19) . . . . ?
C8 C9 C10 F1 178.93(12) . . . . ?
C8 C9 C10 C16 -0.6(2) . . . . ?
C9 C10 C16 C15 0.3(2) . . . . ?
C11 N2 C4 N1 -0.11(14) . . . . ?
C11 N2 C4 C5 -178.35(11) . . . . ?
C11 C12 C13 C1 -0.2(2) . . . . ?
C13 C1 C2 C3 0.2(2) . . . . ?
C14 C5 C6 C7 2.0(2) . . . . ?
C15 C7 C8 C9 0.51(19) . . . . ?

_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_e-cn-bina
_database_code_depnum_ccdc_archive 'CCDC 2240231'
loop_
_audit_author_name
_audit_author_address
'Cheng Liu'
;Jilin University
China
;
_audit_update_record             
;
2023-02-06 deposited with the CCDC.	2023-11-30 downloaded from the CCDC.
;
_audit_creation_date             2023-02-06
_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         'C20 H13 N3'
_chemical_formula_sum            'C20 H13 N3'
_chemical_formula_weight         295.33
_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'
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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.5049(7)
_cell_length_b                   18.4000(12)
_cell_length_c                   17.9978(13)
_cell_angle_alpha                90
_cell_angle_beta                 93.843(2)
_cell_angle_gamma                90
_cell_volume                     3140.6(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5574
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      29.224
_cell_measurement_theta_min      2.607
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.076
_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    1.249
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_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  0.1542
_diffrn_reflns_av_unetI/netI     0.0702
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            72405
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.524
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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                4187
_reflns_number_total             6184
_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         0.370
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     423
_refine_ls_number_reflns         6184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1287
_refine_ls_R_factor_gt           0.0835
_refine_ls_restrained_S_all      1.092
_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)+(0.0676P)²+3.5186P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1684
_refine_ls_wR_factor_ref         0.1879
_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:
 C5(H5), C17(H17), C19(H19), C22(H22), C23(H23), C25(H25), C27(H27), C32(H32),
 C33(H33), C37(H37), C38(H38), C39(H39), C2(H2), C3(H3A), C7(H7), C9(H9),
 C13(H13), C21(H21), C24(H24), C28(H28), C29(H29), C30(H30), C31(H31), C35(H35)
;
_atom_sites_solution_hydrogens   mixed
_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
N1 N 0.1532(3) 0.41034(13) 0.27998(14) 0.0199(6) Uani 1 1 d . . . . .
N3 N 0.2569(3) 0.30145(15) 0.28461(15) 0.0229(6) Uani 1 1 d . . . . .
N5 N 0.3318(4) 0.53003(18) 0.1678(2) 0.0480(9) Uani 1 1 d . . . . .
C5 C -0.0763(4) 0.3233(2) 0.4146(2) 0.0330(8) Uani 1 1 d . . . . .
H5 H -0.1560 0.3308 0.4428 0.040 Uiso 1 1 calc R U . . .
C6 C 0.2545(3) 0.36932(16) 0.25481(16) 0.0202(7) Uani 1 1 d . . . . .
C8 C 0.0854(3) 0.36524(16) 0.32897(17) 0.0207(7) Uani 1 1 d . . . . .
C10 C 0.1517(4) 0.29719(17) 0.33269(17) 0.0220(7) Uani 1 1 d . . . . .
C15 C 0.7963(4) 0.3416(2) 0.0835(2) 0.0405(10) Uani 1 1 d . . . . .
C17 C 0.6275(5) 0.4124(2) 0.0080(2) 0.0472(12) Uani 1 1 d . . . . .
H17 H 0.6031 0.4396 -0.0358 0.057 Uiso 1 1 calc R U . . .
C18 C 0.3536(4) 0.39461(17) 0.20292(18) 0.0242(7) Uani 1 1 d . . . . .
C19 C 0.9308(5) 0.3094(3) 0.0948(3) 0.0547(13) Uani 1 1 d . . . . .
H19 H 0.9974 0.3149 0.0581 0.066 Uiso 1 1 calc R U . . .
C22 C 0.4571(3) 0.35068(17) 0.18006(17) 0.0233(7) Uani 1 1 d . . . . .
H22 H 0.4623 0.3038 0.2022 0.028 Uiso 1 1 calc R U . . .
C23 C -0.0064(4) 0.2567(2) 0.4189(2) 0.0359(9) Uani 1 1 d . . . . .
H23 H -0.0385 0.2205 0.4514 0.043 Uiso 1 1 calc R U . . .
C25 C 0.5279(5) 0.40416(18) 0.0616(2) 0.0354(9) Uani 1 1 d . . . . .
H25 H 0.4370 0.4253 0.0534 0.042 Uiso 1 1 calc R U . . .
C27 C 0.7395(4) 0.2928(2) 0.2034(2) 0.0370(9) Uani 1 1 d . . . . .
H27 H 0.6755 0.2873 0.2414 0.044 Uiso 1 1 calc R U . . .
C32 C -0.0314(4) 0.37899(17) 0.36968(18) 0.0259(7) Uani 1 1 d . . . . .
H32 H -0.0784 0.4246 0.3668 0.031 Uiso 1 1 calc R U . . .
C33 C 0.7571(5) 0.3824(2) 0.0173(2) 0.0454(11) Uani 1 1 d . . . . .
H33 H 0.8224 0.3882 -0.0200 0.055 Uiso 1 1 calc R U . . .
C34 C 0.6980(4) 0.33394(19) 0.1374(2) 0.0311(8) Uani 1 1 d . . . . .
C36 C 0.5613(4) 0.36556(17) 0.12609(19) 0.0265(8) Uani 1 1 d . . . . .
C37 C 0.8682(4) 0.2622(3) 0.2118(2) 0.0488(11) Uani 1 1 d . . . . .
H37 H 0.8924 0.2343 0.2553 0.059 Uiso 1 1 calc R U . . .
C38 C 0.1064(4) 0.24125(18) 0.37846(19) 0.0308(8) Uani 1 1 d . . . . .
H38 H 0.1517 0.1952 0.3811 0.037 Uiso 1 1 calc R U . . .
C39 C 0.9667(5) 0.2701(3) 0.1586(3) 0.0617(15) Uani 1 1 d . . . . .
H39 H 1.0576 0.2487 0.1661 0.074 Uiso 1 1 calc R U . . .
C40 C 0.3409(4) 0.4692(2) 0.18165(19) 0.0311(8) Uani 1 1 d . . . . .
N2 N 0.2073(3) 0.74863(16) 0.41837(16) 0.0317(7) Uani 1 1 d . . . . .
N4 N 0.0633(3) 0.55562(14) 0.25352(15) 0.0216(6) Uani 1 1 d . . . . .
N6 N 0.0658(3) 0.67701(13) 0.24973(14) 0.0202(6) Uani 1 1 d . . . . .
C1 C 0.1088(3) 0.61775(16) 0.28704(17) 0.0185(7) Uani 1 1 d . . . . .
C2 C -0.1517(4) 0.5709(2) 0.0752(2) 0.0409(10) Uani 1 1 d . . . . .
H2 H -0.2004 0.5445 0.0361 0.049 Uiso 1 1 calc R U . . .
C3 C -0.0827(4) 0.53357(18) 0.1328(2) 0.0351(9) Uani 1 1 d . . . . .
H3A H -0.0825 0.4820 0.1344 0.042 Uiso 1 1 calc R U . . .
C4 C -0.0117(3) 0.65086(17) 0.18697(17) 0.0216(7) Uani 1 1 d . . . . .
C7 C -0.1520(4) 0.64729(19) 0.0728(2) 0.0346(9) Uani 1 1 d . . . . .
H7 H -0.2007 0.6713 0.0320 0.042 Uiso 1 1 calc R U . . .
C9 C 0.2419(5) 0.4183(3) 0.6437(2) 0.0478(11) Uani 1 1 d . . . . .
H9 H 0.2244 0.3852 0.6825 0.057 Uiso 1 1 calc R U . . .
C11 C 0.3713(4) 0.5213(2) 0.59788(19) 0.0330(9) Uani 1 1 d . . . . .
C12 C 0.1906(3) 0.62063(17) 0.35861(17) 0.0211(7) Uani 1 1 d . . . . .
C13 C 0.4760(4) 0.5759(2) 0.6081(2) 0.0375(9) Uani 1 1 d . . . . .
H13 H 0.5262 0.5805 0.6553 0.045 Uiso 1 1 calc R U . . .
C14 C 0.2007(3) 0.69253(18) 0.39149(17) 0.0219(7) Uani 1 1 d . . . . .
C16 C -0.0132(3) 0.57463(17) 0.18871(18) 0.0234(7) Uani 1 1 d . . . . .
C20 C 0.2939(4) 0.51590(19) 0.52733(18) 0.0259(8) Uani 1 1 d . . . . .
C21 C 0.4306(4) 0.61648(19) 0.48245(19) 0.0283(8) Uani 1 1 d . . . . .
H21 H 0.4532 0.6484 0.4435 0.034 Uiso 1 1 calc R U . . .
C24 C -0.0837(4) 0.68781(18) 0.12779(19) 0.0287(8) Uani 1 1 d . . . . .
H24 H -0.0850 0.7394 0.1260 0.034 Uiso 1 1 calc R U . . .
C26 C 0.3247(3) 0.56588(18) 0.46966(17) 0.0234(7) Uani 1 1 d . . . . .
C28 C 0.2449(3) 0.56295(18) 0.39692(17) 0.0231(7) Uani 1 1 d . . . . .
H28 H 0.2303 0.5164 0.3749 0.028 Uiso 1 1 calc R U . . .
C29 C 0.5064(4) 0.6214(2) 0.5530(2) 0.0357(9) Uani 1 1 d . . . . .
H29 H 0.5785 0.6569 0.5612 0.043 Uiso 1 1 calc R U . . .
C30 C 0.1894(4) 0.46137(19) 0.51764(19) 0.0294(8) Uani 1 1 d . . . . .
H30 H 0.1347 0.4579 0.4716 0.035 Uiso 1 1 calc R U . . .
C31 C 0.1660(4) 0.4132(2) 0.5740(2) 0.0402(10) Uani 1 1 d . . . . .
H31 H 0.0976 0.3760 0.5658 0.048 Uiso 1 1 calc R U . . .
C35 C 0.3414(5) 0.4719(2) 0.6548(2) 0.0439(11) Uani 1 1 d . . . . .
H35 H 0.3916 0.4758 0.7021 0.053 Uiso 1 1 calc R U . . .
H3 H 0.309(4) 0.2705(19) 0.2716(19) 0.021(10) Uiso 1 1 d . . . . .
H4 H 0.094(4) 0.512(2) 0.267(2) 0.032(10) Uiso 1 1 d . . . . .


_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 C6 1.326(4) . ?
N1 C8 1.399(4) . ?
N3 C6 1.359(4) . ?
N3 C10 1.368(4) . ?
N3 H3 0.80(3) . ?
N5 C40 1.148(5) . ?
C5 H5 0.9500 . ?
C5 C23 1.394(5) . ?
C5 C32 1.390(5) . ?
C6 C18 1.448(5) . ?
C8 C10 1.401(4) . ?
C8 C32 1.393(5) . ?
C10 C38 1.404(5) . ?
C15 C19 1.411(6) . ?
C15 C33 1.436(6) . ?
C15 C34 1.399(5) . ?
C17 H17 0.9500 . ?
C17 C25 1.405(5) . ?
C17 C33 1.350(6) . ?
C18 C22 1.358(5) . ?
C18 C40 1.428(5) . ?
C19 H19 0.9500 . ?
C19 C39 1.382(7) . ?
C22 H22 0.9500 . ?
C22 C36 1.459(5) . ?
C23 H23 0.9500 . ?
C23 C38 1.366(5) . ?
C25 H25 0.9500 . ?
C25 C36 1.379(5) . ?
C27 H27 0.9500 . ?
C27 C34 1.441(5) . ?
C27 C37 1.346(5) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C34 C36 1.426(5) . ?
C37 H37 0.9500 . ?
C37 C39 1.391(7) . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
N2 C14 1.140(4) . ?
N4 C1 1.350(4) . ?
N4 C16 1.378(4) . ?
N4 H4 0.88(4) . ?
N6 C1 1.330(4) . ?
N6 C4 1.392(4) . ?
C1 C12 1.460(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.373(5) . ?
C2 C7 1.406(5) . ?
C3 H3A 0.9500 . ?
C3 C16 1.389(5) . ?
C4 C16 1.403(4) . ?
C4 C24 1.403(5) . ?
C7 H7 0.9500 . ?
C7 C24 1.368(5) . ?
C9 H9 0.9500 . ?
C9 C31 1.407(6) . ?
C9 C35 1.371(6) . ?
C11 C13 1.417(6) . ?
C11 C20 1.428(5) . ?
C11 C35 1.413(5) . ?
C12 C14 1.450(4) . ?
C12 C28 1.349(4) . ?
C13 H13 0.9500 . ?
C13 C29 1.345(6) . ?
C20 C26 1.432(5) . ?
C20 C30 1.414(5) . ?
C21 H21 0.9500 . ?
C21 C26 1.379(5) . ?
C21 C29 1.420(5) . ?
C24 H24 0.9500 . ?
C26 C28 1.469(4) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C30 C31 1.376(5) . ?
C31 H31 0.9500 . ?
C35 H35 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
C6 N1 C8 104.7(2) . . ?
C6 N3 C10 108.0(3) . . ?
C6 N3 H3 122(3) . . ?
C10 N3 H3 130(3) . . ?
C23 C5 H5 119.4 . . ?
C32 C5 H5 119.4 . . ?
C32 C5 C23 121.1(3) . . ?
N1 C6 N3 112.5(3) . . ?
N1 C6 C18 123.8(3) . . ?
N3 C6 C18 123.7(3) . . ?
N1 C8 C10 109.6(3) . . ?
C32 C8 N1 129.8(3) . . ?
C32 C8 C10 120.6(3) . . ?
N3 C10 C8 105.3(3) . . ?
N3 C10 C38 132.8(3) . . ?
C8 C10 C38 121.9(3) . . ?
C19 C15 C33 121.4(4) . . ?
C34 C15 C19 119.9(4) . . ?
C34 C15 C33 118.7(4) . . ?
C25 C17 H17 119.2 . . ?
C33 C17 H17 119.2 . . ?
C33 C17 C25 121.6(4) . . ?
C22 C18 C6 121.3(3) . . ?
C22 C18 C40 122.8(3) . . ?
C40 C18 C6 115.8(3) . . ?
C15 C19 H19 119.6 . . ?
C39 C19 C15 120.7(4) . . ?
C39 C19 H19 119.6 . . ?
C18 C22 H22 115.6 . . ?
C18 C22 C36 128.9(3) . . ?
C36 C22 H22 115.6 . . ?
C5 C23 H23 118.6 . . ?
C38 C23 C5 122.7(3) . . ?
C38 C23 H23 118.6 . . ?
C17 C25 H25 119.8 . . ?
C36 C25 C17 120.3(4) . . ?
C36 C25 H25 119.8 . . ?
C34 C27 H27 119.7 . . ?
C37 C27 H27 119.7 . . ?
C37 C27 C34 120.6(4) . . ?
C5 C32 C8 117.3(3) . . ?
C5 C32 H32 121.4 . . ?
C8 C32 H32 121.4 . . ?
C15 C33 H33 120.0 . . ?
C17 C33 C15 120.0(4) . . ?
C17 C33 H33 120.0 . . ?
C15 C34 C27 117.8(4) . . ?
C15 C34 C36 120.3(4) . . ?
C36 C34 C27 121.9(3) . . ?
C25 C36 C22 121.9(3) . . ?
C25 C36 C34 119.1(3) . . ?
C34 C36 C22 118.7(3) . . ?
C27 C37 H37 119.1 . . ?
C27 C37 C39 121.9(5) . . ?
C39 C37 H37 119.1 . . ?
C10 C38 H38 121.8 . . ?
C23 C38 C10 116.3(3) . . ?
C23 C38 H38 121.8 . . ?
C19 C39 C37 119.1(4) . . ?
C19 C39 H39 120.4 . . ?
C37 C39 H39 120.4 . . ?
N5 C40 C18 176.9(4) . . ?
C1 N4 C16 107.3(3) . . ?
C1 N4 H4 124(2) . . ?
C16 N4 H4 127(2) . . ?
C1 N6 C4 104.7(2) . . ?
N4 C1 C12 124.1(3) . . ?
N6 C1 N4 113.0(3) . . ?
N6 C1 C12 122.9(3) . . ?
C3 C2 H2 119.2 . . ?
C3 C2 C7 121.6(3) . . ?
C7 C2 H2 119.2 . . ?
C2 C3 H3A 121.5 . . ?
C2 C3 C16 117.0(3) . . ?
C16 C3 H3A 121.5 . . ?
N6 C4 C16 109.5(3) . . ?
N6 C4 C24 130.8(3) . . ?
C24 C4 C16 119.8(3) . . ?
C2 C7 H7 119.3 . . ?
C24 C7 C2 121.5(3) . . ?
C24 C7 H7 119.3 . . ?
C31 C9 H9 120.5 . . ?
C35 C9 H9 120.5 . . ?
C35 C9 C31 119.1(4) . . ?
C13 C11 C20 118.7(3) . . ?
C35 C11 C13 122.4(3) . . ?
C35 C11 C20 118.9(4) . . ?
C14 C12 C1 114.2(3) . . ?
C28 C12 C1 125.8(3) . . ?
C28 C12 C14 119.8(3) . . ?
C11 C13 H13 119.0 . . ?
C29 C13 C11 122.0(3) . . ?
C29 C13 H13 119.0 . . ?
N2 C14 C12 178.8(4) . . ?
N4 C16 C3 132.3(3) . . ?
N4 C16 C4 105.5(3) . . ?
C3 C16 C4 122.2(3) . . ?
C11 C20 C26 118.8(3) . . ?
C30 C20 C11 118.3(3) . . ?
C30 C20 C26 122.8(3) . . ?
C26 C21 H21 119.6 . . ?
C26 C21 C29 120.9(3) . . ?
C29 C21 H21 119.6 . . ?
C4 C24 H24 121.0 . . ?
C7 C24 C4 118.0(3) . . ?
C7 C24 H24 121.0 . . ?
C20 C26 C28 120.3(3) . . ?
C21 C26 C20 119.7(3) . . ?
C21 C26 C28 120.1(3) . . ?
C12 C28 C26 125.7(3) . . ?
C12 C28 H28 117.2 . . ?
C26 C28 H28 117.2 . . ?
C13 C29 C21 119.9(4) . . ?
C13 C29 H29 120.1 . . ?
C21 C29 H29 120.1 . . ?
C20 C30 H30 119.6 . . ?
C31 C30 C20 120.8(3) . . ?
C31 C30 H30 119.6 . . ?
C9 C31 H31 119.5 . . ?
C30 C31 C9 121.0(4) . . ?
C30 C31 H31 119.5 . . ?
C9 C35 C11 121.8(4) . . ?
C9 C35 H35 119.1 . . ?
C11 C35 H35 119.1 . . ?

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
N1 C6 C18 C22 178.7(3) . . . . ?
N1 C6 C18 C40 2.6(5) . . . . ?
N1 C8 C10 N3 -1.3(3) . . . . ?
N1 C8 C10 C38 179.3(3) . . . . ?
N1 C8 C32 C5 -179.9(3) . . . . ?
N3 C6 C18 C22 0.4(5) . . . . ?
N3 C6 C18 C40 -175.7(3) . . . . ?
N3 C10 C38 C23 -179.0(4) . . . . ?
C5 C23 C38 C10 1.5(6) . . . . ?
C6 N1 C8 C10 1.1(3) . . . . ?
C6 N1 C8 C32 -177.8(3) . . . . ?
C6 N3 C10 C8 1.0(3) . . . . ?
C6 N3 C10 C38 -179.7(3) . . . . ?
C6 C18 C22 C36 176.9(3) . . . . ?
C8 N1 C6 N3 -0.5(3) . . . . ?
C8 N1 C6 C18 -178.9(3) . . . . ?
C8 C10 C38 C23 0.3(5) . . . . ?
C10 N3 C6 N1 -0.3(4) . . . . ?
C10 N3 C6 C18 178.1(3) . . . . ?
C10 C8 C32 C5 1.3(5) . . . . ?
C15 C19 C39 C37 0.3(7) . . . . ?
C15 C34 C36 C22 174.2(3) . . . . ?
C15 C34 C36 C25 -0.5(5) . . . . ?
C17 C25 C36 C22 -174.7(3) . . . . ?
C17 C25 C36 C34 -0.2(5) . . . . ?
C18 C22 C36 C25 -38.9(5) . . . . ?
C18 C22 C36 C34 146.5(3) . . . . ?
C19 C15 C33 C17 179.8(4) . . . . ?
C19 C15 C34 C27 0.1(5) . . . . ?
C19 C15 C34 C36 -179.3(3) . . . . ?
C23 C5 C32 C8 0.4(5) . . . . ?
C25 C17 C33 C15 -0.7(6) . . . . ?
C27 C34 C36 C22 -5.1(5) . . . . ?
C27 C34 C36 C25 -179.8(3) . . . . ?
C27 C37 C39 C19 -1.1(7) . . . . ?
C32 C5 C23 C38 -1.9(6) . . . . ?
C32 C8 C10 N3 177.7(3) . . . . ?
C32 C8 C10 C38 -1.7(5) . . . . ?
C33 C15 C19 C39 -179.7(4) . . . . ?
C33 C15 C34 C27 180.0(3) . . . . ?
C33 C15 C34 C36 0.6(5) . . . . ?
C33 C17 C25 C36 0.8(6) . . . . ?
C34 C15 C19 C39 0.2(6) . . . . ?
C34 C15 C33 C17 0.0(5) . . . . ?
C34 C27 C37 C39 1.5(6) . . . . ?
C37 C27 C34 C15 -0.9(5) . . . . ?
C37 C27 C34 C36 178.4(4) . . . . ?
C40 C18 C22 C36 -7.2(6) . . . . ?
N4 C1 C12 C14 -167.0(3) . . . . ?
N4 C1 C12 C28 7.7(5) . . . . ?
N6 C1 C12 C14 9.8(4) . . . . ?
N6 C1 C12 C28 -175.5(3) . . . . ?
N6 C4 C16 N4 0.4(4) . . . . ?
N6 C4 C16 C3 -179.9(3) . . . . ?
N6 C4 C24 C7 -180.0(3) . . . . ?
C1 N4 C16 C3 179.4(4) . . . . ?
C1 N4 C16 C4 -0.9(4) . . . . ?
C1 N6 C4 C16 0.2(4) . . . . ?
C1 N6 C4 C24 179.3(4) . . . . ?
C1 C12 C28 C26 -178.7(3) . . . . ?
C2 C3 C16 N4 179.2(4) . . . . ?
C2 C3 C16 C4 -0.5(6) . . . . ?
C2 C7 C24 C4 0.5(6) . . . . ?
C3 C2 C7 C24 -0.1(7) . . . . ?
C4 N6 C1 N4 -0.8(4) . . . . ?
C4 N6 C1 C12 -177.9(3) . . . . ?
C7 C2 C3 C16 0.1(6) . . . . ?
C11 C13 C29 C21 1.3(5) . . . . ?
C11 C20 C26 C21 1.9(5) . . . . ?
C11 C20 C26 C28 -178.6(3) . . . . ?
C11 C20 C30 C31 -2.0(5) . . . . ?
C13 C11 C20 C26 -0.1(5) . . . . ?
C13 C11 C20 C30 -179.8(3) . . . . ?
C13 C11 C35 C9 -178.6(4) . . . . ?
C14 C12 C28 C26 -4.3(5) . . . . ?
C16 N4 C1 N6 1.1(4) . . . . ?
C16 N4 C1 C12 178.2(3) . . . . ?
C16 C4 C24 C7 -0.9(5) . . . . ?
C20 C11 C13 C29 -1.5(5) . . . . ?
C20 C11 C35 C9 1.1(6) . . . . ?
C20 C26 C28 C12 134.5(4) . . . . ?
C20 C30 C31 C9 2.2(6) . . . . ?
C21 C26 C28 C12 -46.1(5) . . . . ?
C24 C4 C16 N4 -178.8(3) . . . . ?
C24 C4 C16 C3 0.9(5) . . . . ?
C26 C20 C30 C31 178.2(3) . . . . ?
C26 C21 C29 C13 0.7(5) . . . . ?
C29 C21 C26 C20 -2.3(5) . . . . ?
C29 C21 C26 C28 178.3(3) . . . . ?
C30 C20 C26 C21 -178.3(3) . . . . ?
C30 C20 C26 C28 1.1(5) . . . . ?
C31 C9 C35 C11 -1.0(6) . . . . ?
C35 C9 C31 C30 -0.7(6) . . . . ?
C35 C11 C13 C29 178.2(4) . . . . ?
C35 C11 C20 C26 -179.8(3) . . . . ?
C35 C11 C20 C30 0.4(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-bifph-cn
_database_code_depnum_ccdc_archive 'CCDC 2240227'
loop_
_audit_author_name
_audit_author_address
'Cheng Liu'
;Jilin University
China
;
_audit_update_record             
;
2023-02-06 deposited with the CCDC.	2023-11-30 downloaded from the CCDC.
;
_audit_creation_date             2023-02-06
_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         'C16 H10 F N3'
_chemical_formula_sum            'C16 H10 F N3'
_chemical_formula_weight         263.27
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   15.8850(6)
_cell_length_b                   7.1306(2)
_cell_length_c                   22.5916(8)
_cell_angle_alpha                90
_cell_angle_beta                 103.786(2)
_cell_angle_gamma                90
_cell_volume                     2485.22(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9952
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      29.563
_cell_measurement_theta_min      2.640
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.097
_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 green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.15
_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  0.0886
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            56078
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.582
_diffrn_reflns_theta_min         2.641
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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                4708
_reflns_number_total             6936
_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         0.360
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         6936
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0483
_refine_ls_restrained_S_all      1.011
_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)+(0.0364P)²+1.6040P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.1169
_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(H2A), C3(H3), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C18(H18), C19(H19), C22(H22), C25(H25), C26(H26), C27(H27), C28(H28),
  C30(H30), C31(H31)
;
_atom_sites_solution_hydrogens   mixed
_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 1.13527(7) 0.79171(18) 0.56436(5) 0.0396(3) Uani 1 1 d . . . . .
F2 F 0.10868(7) -0.10526(15) 0.43145(5) 0.0294(2) Uani 1 1 d . . . . .
N1 N 0.69400(9) 0.38017(18) 0.68996(6) 0.0188(3) Uani 1 1 d . . . . .
N2 N 0.62773(9) 0.37870(19) 0.59024(6) 0.0179(3) Uani 1 1 d . . . . .
N3 N 0.70093(10) 0.4714(2) 0.46570(7) 0.0293(3) Uani 1 1 d . . . . .
N4 N 0.49247(9) 0.26879(19) 0.23722(6) 0.0194(3) Uani 1 1 d . . . . .
N5 N 0.53430(10) 0.2523(2) 0.46566(6) 0.0271(3) Uani 1 1 d . . . . .
N6 N 0.57231(9) 0.32188(19) 0.33206(6) 0.0188(3) Uani 1 1 d . . . . .
C1 C 1.05614(11) 0.7219(3) 0.56570(8) 0.0259(4) Uani 1 1 d . . . . .
C2 C 1.04689(12) 0.6283(3) 0.61696(8) 0.0285(4) Uani 1 1 d . . . . .
H2A H 1.0949 0.6135 0.6509 0.034 Uiso 1 1 calc R U . . .
C3 C 0.96641(11) 0.5559(2) 0.61833(8) 0.0234(4) Uani 1 1 d . . . . .
H3 H 0.9594 0.4889 0.6532 0.028 Uiso 1 1 calc R U . . .
C4 C 0.89541(10) 0.5809(2) 0.56867(7) 0.0182(3) Uani 1 1 d . . . . .
C5 C 0.80804(10) 0.5138(2) 0.57109(7) 0.0174(3) Uani 1 1 d . . . . .
C6 C 0.78441(10) 0.4762(2) 0.62356(7) 0.0191(3) Uani 1 1 d . . . . .
H6 H 0.8287 0.4953 0.6596 0.023 Uiso 1 1 calc R U . . .
C7 C 0.70283(10) 0.4118(2) 0.63382(7) 0.0169(3) Uani 1 1 d . . . . .
C8 C 0.60923(10) 0.3193(2) 0.68255(7) 0.0178(3) Uani 1 1 d . . . . .
C9 C 0.56434(11) 0.2628(2) 0.72606(8) 0.0213(3) Uani 1 1 d . . . . .
H9 H 0.5921 0.2608 0.7682 0.026 Uiso 1 1 calc R U . . .
C10 C 0.47886(11) 0.2104(2) 0.70568(8) 0.0239(4) Uani 1 1 d . . . . .
H10 H 0.4474 0.1719 0.7344 0.029 Uiso 1 1 calc R U . . .
C11 C 0.98848(12) 0.7454(2) 0.51528(8) 0.0240(4) Uani 1 1 d . . . . .
H11 H 0.9967 0.8092 0.4802 0.029 Uiso 1 1 calc R U . . .
C12 C 0.90829(11) 0.6735(2) 0.51714(8) 0.0215(3) Uani 1 1 d . . . . .
H12 H 0.8610 0.6874 0.4826 0.026 Uiso 1 1 calc R U . . .
C13 C 0.43708(11) 0.2125(2) 0.64342(8) 0.0242(4) Uani 1 1 d . . . . .
H13 H 0.3780 0.1757 0.6310 0.029 Uiso 1 1 calc R U . . .
C14 C 0.48018(11) 0.2671(2) 0.59979(8) 0.0222(3) Uani 1 1 d . . . . .
H14 H 0.4520 0.2694 0.5577 0.027 Uiso 1 1 calc R U . . .
C15 C 0.56681(10) 0.3183(2) 0.62038(7) 0.0180(3) Uani 1 1 d . . . . .
C16 C 0.74717(11) 0.4903(2) 0.51292(7) 0.0206(3) Uani 1 1 d . . . . .
C17 C 0.18146(11) -0.0366(2) 0.41778(8) 0.0206(3) Uani 1 1 d . . . . .
C18 C 0.25278(11) -0.0008(2) 0.46423(7) 0.0218(3) Uani 1 1 d . . . . .
H18 H 0.2515 -0.0216 0.5055 0.026 Uiso 1 1 calc R U . . .
C19 C 0.32693(11) 0.0668(2) 0.44894(7) 0.0198(3) Uani 1 1 d . . . . .
H19 H 0.3771 0.0922 0.4804 0.024 Uiso 1 1 calc R U . . .
C20 C 0.32907(10) 0.0983(2) 0.38821(7) 0.0165(3) Uani 1 1 d . . . . .
C21 C 0.40888(10) 0.1699(2) 0.37306(7) 0.0165(3) Uani 1 1 d . . . . .
C22 C 0.41954(10) 0.1966(2) 0.31600(7) 0.0179(3) Uani 1 1 d . . . . .
H22 H 0.3704 0.1677 0.2841 0.021 Uiso 1 1 calc R U . . .
C23 C 0.49443(10) 0.2626(2) 0.29630(7) 0.0173(3) Uani 1 1 d . . . . .
C24 C 0.57240(10) 0.3396(2) 0.23434(7) 0.0189(3) Uani 1 1 d . . . . .
C25 C 0.60497(11) 0.3825(2) 0.18348(8) 0.0247(4) Uani 1 1 d . . . . .
H25 H 0.5717 0.3599 0.1432 0.030 Uiso 1 1 calc R U . . .
C26 C 0.68719(12) 0.4589(3) 0.19396(8) 0.0278(4) Uani 1 1 d . . . . .
H26 H 0.7107 0.4891 0.1602 0.033 Uiso 1 1 calc R U . . .
C27 C 0.18070(10) -0.0103(2) 0.35722(8) 0.0206(3) Uani 1 1 d . . . . .
H27 H 0.1305 -0.0388 0.3262 0.025 Uiso 1 1 calc R U . . .
C28 C 0.25474(10) 0.0585(2) 0.34262(7) 0.0194(3) Uani 1 1 d . . . . .
H28 H 0.2550 0.0789 0.3011 0.023 Uiso 1 1 calc R U . . .
C29 C 0.47937(11) 0.2140(2) 0.42427(7) 0.0193(3) Uani 1 1 d . . . . .
C30 C 0.73666(12) 0.4929(2) 0.25322(8) 0.0266(4) Uani 1 1 d . . . . .
H30 H 0.7928 0.5462 0.2585 0.032 Uiso 1 1 calc R U . . .
C31 C 0.70623(11) 0.4513(2) 0.30403(8) 0.0239(4) Uani 1 1 d . . . . .
H31 H 0.7399 0.4739 0.3441 0.029 Uiso 1 1 calc R U . . .
C32 C 0.62330(10) 0.3743(2) 0.29325(7) 0.0187(3) Uani 1 1 d . . . . .
H2 H 0.6231(14) 0.375(3) 0.5508(10) 0.036(6) Uiso 1 1 d . . . . .
H6A H 0.5829(14) 0.339(3) 0.3710(10) 0.037(6) Uiso 1 1 d . . . . .


_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 1.359(2) . ?
F2 C17 1.3572(18) . ?
N1 C7 1.328(2) . ?
N1 C8 1.386(2) . ?
N2 C7 1.374(2) . ?
N2 C15 1.378(2) . ?
N2 H2 0.88(2) . ?
N3 C16 1.150(2) . ?
N4 C23 1.328(2) . ?
N4 C24 1.382(2) . ?
N5 C29 1.149(2) . ?
N6 C23 1.373(2) . ?
N6 C32 1.379(2) . ?
N6 H6A 0.86(2) . ?
C1 C2 1.374(3) . ?
C1 C11 1.377(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.386(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.400(2) . ?
C4 C5 1.481(2) . ?
C4 C12 1.395(2) . ?
C5 C6 1.353(2) . ?
C5 C16 1.444(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.445(2) . ?
C8 C9 1.404(2) . ?
C8 C15 1.406(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.377(2) . ?
C10 H10 0.9500 . ?
C10 C13 1.405(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.383(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C13 C14 1.383(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.392(2) . ?
C17 C18 1.372(2) . ?
C17 C27 1.378(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.391(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.399(2) . ?
C20 C21 1.481(2) . ?
C20 C28 1.399(2) . ?
C21 C22 1.353(2) . ?
C21 C29 1.440(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.445(2) . ?
C24 C25 1.402(2) . ?
C24 C32 1.405(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.382(3) . ?
C26 H26 0.9500 . ?
C26 C30 1.403(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.385(2) . ?
C28 H28 0.9500 . ?
C30 H30 0.9500 . ?
C30 C31 1.380(2) . ?
C31 H31 0.9500 . ?
C31 C32 1.394(2) . ?

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 C8 104.97(13) . . ?
C7 N2 C15 106.95(13) . . ?
C7 N2 H2 125.5(14) . . ?
C15 N2 H2 126.5(14) . . ?
C23 N4 C24 104.93(13) . . ?
C23 N6 C32 107.00(13) . . ?
C23 N6 H6A 125.0(14) . . ?
C32 N6 H6A 127.3(15) . . ?
F1 C1 C2 118.80(16) . . ?
F1 C1 C11 118.72(16) . . ?
C2 C1 C11 122.47(16) . . ?
C1 C2 H2A 120.5 . . ?
C1 C2 C3 118.95(17) . . ?
C3 C2 H2A 120.5 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.39(16) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 120.81(14) . . ?
C12 C4 C3 118.60(15) . . ?
C12 C4 C5 120.58(14) . . ?
C6 C5 C4 123.67(14) . . ?
C6 C5 C16 120.62(15) . . ?
C16 C5 C4 115.71(14) . . ?
C5 C6 H6 114.7 . . ?
C5 C6 C7 130.57(15) . . ?
C7 C6 H6 114.7 . . ?
N1 C7 N2 112.58(14) . . ?
N1 C7 C6 120.67(14) . . ?
N2 C7 C6 126.75(14) . . ?
N1 C8 C9 130.23(15) . . ?
N1 C8 C15 110.05(14) . . ?
C9 C8 C15 119.71(15) . . ?
C8 C9 H9 121.0 . . ?
C10 C9 C8 117.94(15) . . ?
C10 C9 H9 121.0 . . ?
C9 C10 H10 119.2 . . ?
C9 C10 C13 121.64(16) . . ?
C13 C10 H10 119.2 . . ?
C1 C11 H11 120.9 . . ?
C1 C11 C12 118.20(16) . . ?
C12 C11 H11 120.9 . . ?
C4 C12 H12 119.3 . . ?
C11 C12 C4 121.34(16) . . ?
C11 C12 H12 119.3 . . ?
C10 C13 H13 119.3 . . ?
C14 C13 C10 121.36(16) . . ?
C14 C13 H13 119.3 . . ?
C13 C14 H14 121.5 . . ?
C13 C14 C15 116.96(16) . . ?
C15 C14 H14 121.5 . . ?
N2 C15 C8 105.44(14) . . ?
N2 C15 C14 132.17(15) . . ?
C14 C15 C8 122.37(15) . . ?
N3 C16 C5 177.76(18) . . ?
F2 C17 C18 119.06(15) . . ?
F2 C17 C27 117.94(15) . . ?
C18 C17 C27 122.98(15) . . ?
C17 C18 H18 121.0 . . ?
C17 C18 C19 117.92(15) . . ?
C19 C18 H18 121.0 . . ?
C18 C19 H19 119.4 . . ?
C18 C19 C20 121.29(15) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 C21 120.29(14) . . ?
C28 C20 C19 118.44(15) . . ?
C28 C20 C21 121.26(14) . . ?
C22 C21 C20 125.25(14) . . ?
C22 C21 C29 119.00(14) . . ?
C29 C21 C20 115.75(13) . . ?
C21 C22 H22 115.2 . . ?
C21 C22 C23 129.68(15) . . ?
C23 C22 H22 115.2 . . ?
N4 C23 N6 112.53(14) . . ?
N4 C23 C22 119.77(14) . . ?
N6 C23 C22 127.70(14) . . ?
N4 C24 C25 129.86(15) . . ?
N4 C24 C32 110.33(14) . . ?
C25 C24 C32 119.78(15) . . ?
C24 C25 H25 121.2 . . ?
C26 C25 C24 117.63(16) . . ?
C26 C25 H25 121.2 . . ?
C25 C26 H26 119.2 . . ?
C25 C26 C30 121.54(17) . . ?
C30 C26 H26 119.2 . . ?
C17 C27 H27 120.7 . . ?
C17 C27 C28 118.53(15) . . ?
C28 C27 H27 120.7 . . ?
C20 C28 H28 119.6 . . ?
C27 C28 C20 120.82(15) . . ?
C27 C28 H28 119.6 . . ?
N5 C29 C21 178.30(18) . . ?
C26 C30 H30 119.0 . . ?
C31 C30 C26 121.96(16) . . ?
C31 C30 H30 119.0 . . ?
C30 C31 H31 121.8 . . ?
C30 C31 C32 116.31(16) . . ?
C32 C31 H31 121.8 . . ?
N6 C32 C24 105.19(14) . . ?
N6 C32 C31 132.01(15) . . ?
C31 C32 C24 122.78(15) . . ?

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 -179.60(16) . . . . ?
F1 C1 C11 C12 179.91(15) . . . . ?
F2 C17 C18 C19 179.05(14) . . . . ?
F2 C17 C27 C28 -179.57(14) . . . . ?
N1 C8 C9 C10 179.26(16) . . . . ?
N1 C8 C15 N2 0.35(17) . . . . ?
N1 C8 C15 C14 -178.57(14) . . . . ?
N4 C24 C25 C26 177.70(16) . . . . ?
N4 C24 C32 N6 0.27(18) . . . . ?
N4 C24 C32 C31 -178.07(15) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
C1 C11 C12 C4 0.6(3) . . . . ?
C2 C1 C11 C12 0.8(3) . . . . ?
C2 C3 C4 C5 -176.42(16) . . . . ?
C2 C3 C4 C12 2.5(2) . . . . ?
C3 C4 C5 C6 19.8(2) . . . . ?
C3 C4 C5 C16 -160.52(15) . . . . ?
C3 C4 C12 C11 -2.2(2) . . . . ?
C4 C5 C6 C7 179.54(15) . . . . ?
C5 C4 C12 C11 176.72(15) . . . . ?
C5 C6 C7 N1 178.76(16) . . . . ?
C5 C6 C7 N2 -2.1(3) . . . . ?
C7 N1 C8 C9 178.85(16) . . . . ?
C7 N1 C8 C15 -1.00(17) . . . . ?
C7 N2 C15 C8 0.43(17) . . . . ?
C7 N2 C15 C14 179.20(17) . . . . ?
C8 N1 C7 N2 1.32(17) . . . . ?
C8 N1 C7 C6 -179.42(14) . . . . ?
C8 C9 C10 C13 0.1(2) . . . . ?
C9 C8 C15 N2 -179.53(14) . . . . ?
C9 C8 C15 C14 1.6(2) . . . . ?
C9 C10 C13 C14 0.2(3) . . . . ?
C10 C13 C14 C15 0.4(2) . . . . ?
C11 C1 C2 C3 -0.5(3) . . . . ?
C12 C4 C5 C6 -159.11(16) . . . . ?
C12 C4 C5 C16 20.6(2) . . . . ?
C13 C14 C15 N2 -179.89(16) . . . . ?
C13 C14 C15 C8 -1.3(2) . . . . ?
C15 N2 C7 N1 -1.13(18) . . . . ?
C15 N2 C7 C6 179.65(15) . . . . ?
C15 C8 C9 C10 -0.9(2) . . . . ?
C16 C5 C6 C7 -0.2(3) . . . . ?
C17 C18 C19 C20 0.2(2) . . . . ?
C17 C27 C28 C20 0.8(2) . . . . ?
C18 C17 C27 C28 -1.2(3) . . . . ?
C18 C19 C20 C21 -179.83(15) . . . . ?
C18 C19 C20 C28 -0.6(2) . . . . ?
C19 C20 C21 C22 176.60(15) . . . . ?
C19 C20 C21 C29 -3.7(2) . . . . ?
C19 C20 C28 C27 0.1(2) . . . . ?
C20 C21 C22 C23 -178.98(15) . . . . ?
C21 C20 C28 C27 179.32(15) . . . . ?
C21 C22 C23 N4 176.29(16) . . . . ?
C21 C22 C23 N6 -3.1(3) . . . . ?
C23 N4 C24 C25 -177.38(17) . . . . ?
C23 N4 C24 C32 0.63(18) . . . . ?
C23 N6 C32 C24 -1.05(17) . . . . ?
C23 N6 C32 C31 177.08(17) . . . . ?
C24 N4 C23 N6 -1.34(18) . . . . ?
C24 N4 C23 C22 179.19(14) . . . . ?
C24 C25 C26 C30 -0.1(3) . . . . ?
C25 C24 C32 N6 178.52(15) . . . . ?
C25 C24 C32 C31 0.2(2) . . . . ?
C25 C26 C30 C31 0.3(3) . . . . ?
C26 C30 C31 C32 -0.3(3) . . . . ?
C27 C17 C18 C19 0.7(3) . . . . ?
C28 C20 C21 C22 -2.6(2) . . . . ?
C28 C20 C21 C29 177.06(14) . . . . ?
C29 C21 C22 C23 1.3(3) . . . . ?
C30 C31 C32 N6 -177.80(17) . . . . ?
C30 C31 C32 C24 0.0(2) . . . . ?
C32 N6 C23 N4 1.55(18) . . . . ?
C32 N6 C23 C22 -179.04(15) . . . . ?
C32 C24 C25 C26 -0.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
