# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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. 
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data_11
_database_code_depnum_ccdc_archive 'CCDC 2498970'
loop_
_audit_author_name
_audit_author_address
chenkairong
;shiheziuniversity
China
;
_audit_update_record             
;
2025-10-30 deposited with the CCDC.	2026-03-10 downloaded from the CCDC.
;
_audit_creation_date             2025-05-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        
11-Benzyl-3-(4-chlorophenyl)-5,6-dihydroindolizino[8,7-b]indole
_chemical_formula_moiety         'C27 H21 Cl N2'
_chemical_formula_sum            'C27 H21 Cl N2'
_chemical_formula_weight         408.91
_chemical_melting_point          227.3-228.7
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_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                   13.8440(6)
_cell_length_b                   11.6532(5)
_cell_length_c                   12.5453(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.307(3)
_cell_angle_gamma                90
_cell_volume                     1997.25(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6412
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      71.85
_cell_measurement_theta_min      3.23
_shelx_estimated_absorpt_T_max   0.786
_shelx_estimated_absorpt_T_min   0.737
_exptl_absorpt_coefficient_mu    1.808
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1077 before and 0.0711 after correction.
The Ratio of minimum to maximum transmission is 0.7521.
The λ/2 correction factor is Not present.
;
_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    1.360
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12277
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.182
_diffrn_reflns_theta_min         3.235
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_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                3208
_reflns_number_total             3886
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0025(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3886
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0505
_refine_ls_restrained_S_all      1.081
_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)+(0.0564P)²+0.9590P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1381
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C15(H15A,H15B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
 C18(H18), C19(H19), C23(H23), C24(H24), C26(H26), C27(H27)
;
_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
C1 C 0.16502(17) 0.23843(18) 0.39521(17) 0.0353(5) Uani 1 1 d . . . . .
H1A H 0.138864 0.214758 0.460777 0.042 Uiso 1 1 calc R U . . .
H1B H 0.209175 0.176833 0.377758 0.042 Uiso 1 1 calc R U . . .
C2 C 0.08070(17) 0.25008(19) 0.30260(17) 0.0361(5) Uani 1 1 d . . . . .
C3 C 0.07660(18) 0.3372(2) 0.22684(18) 0.0419(5) Uani 1 1 d . . . . .
H3 H 0.126911 0.393397 0.233837 0.050 Uiso 1 1 calc R U . . .
C4 C -0.0001(2) 0.3432(2) 0.1409(2) 0.0533(7) Uani 1 1 d . . . . .
H4 H -0.001687 0.403172 0.089281 0.064 Uiso 1 1 calc R U . . .
C5 C -0.0737(2) 0.2629(3) 0.1300(2) 0.0585(8) Uani 1 1 d . . . . .
H5 H -0.126221 0.267336 0.071258 0.070 Uiso 1 1 calc R U . . .
C6 C -0.0710(2) 0.1761(3) 0.2045(3) 0.0613(8) Uani 1 1 d . . . . .
H6 H -0.121620 0.120264 0.196912 0.074 Uiso 1 1 calc R U . . .
C7 C 0.0056(2) 0.1695(2) 0.2910(2) 0.0486(6) Uani 1 1 d . . . . .
H7 H 0.006601 0.109514 0.342445 0.058 Uiso 1 1 calc R U . . .
C8 C 0.19891(16) 0.42833(18) 0.48798(15) 0.0304(4) Uani 1 1 d . . . . .
C9 C 0.12495(16) 0.4329(2) 0.55138(16) 0.0361(5) Uani 1 1 d . . . . .
H9 H 0.079616 0.371738 0.551679 0.043 Uiso 1 1 calc R U . . .
C10 C 0.12026(18) 0.5298(2) 0.61371(17) 0.0404(5) Uani 1 1 d . . . . .
H10 H 0.070609 0.535357 0.657614 0.048 Uiso 1 1 calc R U . . .
C11 C 0.18675(17) 0.6199(2) 0.61370(16) 0.0382(5) Uani 1 1 d . . . . .
H11 H 0.181571 0.685103 0.657886 0.046 Uiso 1 1 calc R U . . .
C12 C 0.26024(16) 0.61625(19) 0.55055(15) 0.0327(5) Uani 1 1 d . . . . .
H12 H 0.304977 0.678130 0.550946 0.039 Uiso 1 1 calc R U . . .
C13 C 0.26701(15) 0.51883(18) 0.48591(14) 0.0291(4) Uani 1 1 d . . . . .
C14 C 0.33002(15) 0.48661(17) 0.41167(14) 0.0289(4) Uani 1 1 d . . . . .
C15 C 0.40720(16) 0.55114(18) 0.36723(16) 0.0331(5) Uani 1 1 d . . . . .
H15A H 0.444972 0.598324 0.425102 0.040 Uiso 1 1 calc R U . . .
H15B H 0.376150 0.603481 0.309534 0.040 Uiso 1 1 calc R U . . .
C16 C 0.47597(16) 0.47024(18) 0.32168(16) 0.0331(5) Uani 1 1 d . . . . .
H16A H 0.513980 0.514146 0.275063 0.040 Uiso 1 1 calc R U . . .
H16B H 0.522780 0.437228 0.381880 0.040 Uiso 1 1 calc R U . . .
C17 C 0.44884(15) 0.32113(18) 0.16931(15) 0.0305(4) Uani 1 1 d . . . . .
C18 C 0.38181(16) 0.23356(19) 0.14261(16) 0.0344(5) Uani 1 1 d . . . . .
H18 H 0.380799 0.181311 0.084311 0.041 Uiso 1 1 calc R U . . .
C19 C 0.31542(16) 0.23503(19) 0.21640(16) 0.0341(5) Uani 1 1 d . . . . .
H19 H 0.262127 0.183852 0.217198 0.041 Uiso 1 1 calc R U . . .
C20 C 0.34176(15) 0.32433(17) 0.28748(15) 0.0293(4) Uani 1 1 d . . . . .
C21 C 0.29975(15) 0.37998(17) 0.37158(14) 0.0285(4) Uani 1 1 d . . . . .
C22 C 0.52851(16) 0.35530(17) 0.11202(15) 0.0314(4) Uani 1 1 d . . . . .
C23 C 0.62026(16) 0.3918(2) 0.16316(16) 0.0352(5) Uani 1 1 d . . . . .
H23 H 0.633385 0.394530 0.239827 0.042 Uiso 1 1 calc R U . . .
C24 C 0.69271(18) 0.4240(2) 0.10514(18) 0.0398(5) Uani 1 1 d . . . . .
H24 H 0.754393 0.449915 0.141527 0.048 Uiso 1 1 calc R U . . .
C25 C 0.67430(19) 0.4181(2) -0.00702(18) 0.0401(5) Uani 1 1 d . . . . .
C26 C 0.58493(18) 0.3784(2) -0.06024(16) 0.0398(5) Uani 1 1 d . . . . .
H26 H 0.573357 0.372055 -0.136739 0.048 Uiso 1 1 calc R U . . .
C27 C 0.51307(17) 0.34822(18) -0.00130(16) 0.0353(5) Uani 1 1 d . . . . .
H27 H 0.451655 0.322002 -0.038118 0.042 Uiso 1 1 calc R U . . .
Cl1 Cl 0.76457(5) 0.45873(6) -0.08105(5) 0.0576(2) Uani 1 1 d . . . . .
N1 N 0.22146(13) 0.34303(15) 0.41871(13) 0.0309(4) Uani 1 1 d . . . . .
N2 N 0.42374(13) 0.37664(14) 0.25851(12) 0.0282(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
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.514(3) . ?
C1 N1 1.452(3) . ?
C2 C3 1.385(3) . ?
C2 C7 1.391(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.375(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.373(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.390(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.396(3) . ?
C8 C13 1.418(3) . ?
C8 N1 1.389(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.381(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.396(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.388(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.407(3) . ?
C13 C14 1.425(3) . ?
C14 C15 1.487(3) . ?
C14 C21 1.380(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.516(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 N2 1.468(2) . ?
C17 C18 1.384(3) . ?
C17 C22 1.466(3) . ?
C17 N2 1.385(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.406(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.381(3) . ?
C20 C21 1.439(3) . ?
C20 N2 1.388(3) . ?
C21 N1 1.385(3) . ?
C22 C23 1.394(3) . ?
C22 C27 1.405(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.383(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.391(3) . ?
C25 C26 1.387(4) . ?
C25 Cl1 1.739(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.378(3) . ?
C27 H27 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
H1A C1 H1B 107.7 . . ?
C2 C1 H1A 108.8 . . ?
C2 C1 H1B 108.8 . . ?
N1 C1 H1A 108.8 . . ?
N1 C1 H1B 108.8 . . ?
N1 C1 C2 113.78(17) . . ?
C3 C2 C1 122.2(2) . . ?
C3 C2 C7 118.4(2) . . ?
C7 C2 C1 119.4(2) . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.8(2) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.8(2) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.3(3) . . ?
C7 C6 H6 119.8 . . ?
C2 C7 H7 119.8 . . ?
C6 C7 C2 120.4(3) . . ?
C6 C7 H7 119.8 . . ?
C9 C8 C13 122.2(2) . . ?
N1 C8 C9 130.1(2) . . ?
N1 C8 C13 107.67(18) . . ?
C8 C9 H9 121.3 . . ?
C10 C9 C8 117.4(2) . . ?
C10 C9 H9 121.3 . . ?
C9 C10 H10 119.2 . . ?
C9 C10 C11 121.6(2) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.4(2) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 H12 120.7 . . ?
C11 C12 C13 118.5(2) . . ?
C13 C12 H12 120.7 . . ?
C8 C13 C14 107.16(17) . . ?
C12 C13 C8 118.90(19) . . ?
C12 C13 C14 133.9(2) . . ?
C13 C14 C15 131.65(18) . . ?
C21 C14 C13 107.07(18) . . ?
C21 C14 C15 120.86(18) . . ?
C14 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
C14 C15 C16 111.11(17) . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C15 C16 H16A 109.1 . . ?
C15 C16 H16B 109.1 . . ?
H16A C16 H16B 107.9 . . ?
N2 C16 C15 112.39(18) . . ?
N2 C16 H16A 109.1 . . ?
N2 C16 H16B 109.1 . . ?
C18 C17 C22 127.60(18) . . ?
C18 C17 N2 107.10(18) . . ?
N2 C17 C22 125.21(18) . . ?
C17 C18 H18 125.8 . . ?
C17 C18 C19 108.41(18) . . ?
C19 C18 H18 125.8 . . ?
C18 C19 H19 126.2 . . ?
C20 C19 C18 107.58(19) . . ?
C20 C19 H19 126.2 . . ?
C19 C20 C21 135.9(2) . . ?
C19 C20 N2 107.68(18) . . ?
N2 C20 C21 116.03(17) . . ?
C14 C21 C20 122.56(19) . . ?
C14 C21 N1 109.68(18) . . ?
N1 C21 C20 127.60(18) . . ?
C23 C22 C17 124.00(18) . . ?
C23 C22 C27 117.5(2) . . ?
C27 C22 C17 118.47(19) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 C22 121.67(19) . . ?
C24 C23 H23 119.2 . . ?
C23 C24 H24 120.4 . . ?
C23 C24 C25 119.3(2) . . ?
C25 C24 H24 120.4 . . ?
C24 C25 Cl1 119.8(2) . . ?
C26 C25 C24 120.5(2) . . ?
C26 C25 Cl1 119.73(17) . . ?
C25 C26 H26 120.3 . . ?
C27 C26 C25 119.5(2) . . ?
C27 C26 H26 120.3 . . ?
C22 C27 H27 119.2 . . ?
C26 C27 C22 121.5(2) . . ?
C26 C27 H27 119.2 . . ?
C8 N1 C1 124.05(18) . . ?
C21 N1 C1 127.37(18) . . ?
C21 N1 C8 108.39(17) . . ?
C17 N2 C16 128.12(18) . . ?
C17 N2 C20 109.22(16) . . ?
C20 N2 C16 122.51(16) . . ?

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
C1 C2 C3 C4 177.8(2) . . . . ?
C1 C2 C7 C6 -177.8(2) . . . . ?
C2 C1 N1 C8 87.5(2) . . . . ?
C2 C1 N1 C21 -86.8(3) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C3 C2 C7 C6 0.7(4) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C4 C5 C6 C7 0.3(4) . . . . ?
C5 C6 C7 C2 -0.5(4) . . . . ?
C7 C2 C3 C4 -0.6(4) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C8 C13 C14 C15 172.24(19) . . . . ?
C8 C13 C14 C21 -0.1(2) . . . . ?
C9 C8 C13 C12 0.5(3) . . . . ?
C9 C8 C13 C14 -178.81(18) . . . . ?
C9 C8 N1 C1 3.0(3) . . . . ?
C9 C8 N1 C21 178.2(2) . . . . ?
C9 C10 C11 C12 0.4(3) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C11 C12 C13 C8 -0.2(3) . . . . ?
C11 C12 C13 C14 178.9(2) . . . . ?
C12 C13 C14 C15 -6.9(4) . . . . ?
C12 C13 C14 C21 -179.2(2) . . . . ?
C13 C8 C9 C10 -0.3(3) . . . . ?
C13 C8 N1 C1 -176.97(17) . . . . ?
C13 C8 N1 C21 -1.8(2) . . . . ?
C13 C14 C15 C16 160.92(19) . . . . ?
C13 C14 C21 C20 174.82(17) . . . . ?
C13 C14 C21 N1 -0.9(2) . . . . ?
C14 C15 C16 N2 42.9(2) . . . . ?
C14 C21 N1 C1 176.71(18) . . . . ?
C14 C21 N1 C8 1.7(2) . . . . ?
C15 C14 C21 C20 1.4(3) . . . . ?
C15 C14 C21 N1 -174.33(17) . . . . ?
C15 C16 N2 C17 147.74(19) . . . . ?
C15 C16 N2 C20 -37.3(3) . . . . ?
C17 C18 C19 C20 0.5(2) . . . . ?
C17 C22 C23 C24 -179.4(2) . . . . ?
C17 C22 C27 C26 -179.7(2) . . . . ?
C18 C17 C22 C23 -142.5(2) . . . . ?
C18 C17 C22 C27 35.7(3) . . . . ?
C18 C17 N2 C16 175.55(19) . . . . ?
C18 C17 N2 C20 0.0(2) . . . . ?
C18 C19 C20 C21 171.2(2) . . . . ?
C18 C19 C20 N2 -0.5(2) . . . . ?
C19 C20 C21 C14 -162.8(2) . . . . ?
C19 C20 C21 N1 12.1(4) . . . . ?
C19 C20 N2 C16 -175.54(18) . . . . ?
C19 C20 N2 C17 0.3(2) . . . . ?
C20 C21 N1 C1 1.2(3) . . . . ?
C20 C21 N1 C8 -173.79(18) . . . . ?
C21 C14 C15 C16 -27.6(3) . . . . ?
C21 C20 N2 C16 10.9(3) . . . . ?
C21 C20 N2 C17 -173.31(16) . . . . ?
C22 C17 C18 C19 -176.97(19) . . . . ?
C22 C17 N2 C16 -7.7(3) . . . . ?
C22 C17 N2 C20 176.78(18) . . . . ?
C22 C23 C24 C25 -1.1(3) . . . . ?
C23 C22 C27 C26 -1.4(3) . . . . ?
C23 C24 C25 C26 -1.2(3) . . . . ?
C23 C24 C25 Cl1 179.84(18) . . . . ?
C24 C25 C26 C27 2.1(3) . . . . ?
C25 C26 C27 C22 -0.8(3) . . . . ?
C27 C22 C23 C24 2.3(3) . . . . ?
Cl1 C25 C26 C27 -178.89(17) . . . . ?
N1 C1 C2 C3 19.5(3) . . . . ?
N1 C1 C2 C7 -162.1(2) . . . . ?
N1 C8 C9 C10 179.70(19) . . . . ?
N1 C8 C13 C12 -179.57(17) . . . . ?
N1 C8 C13 C14 1.2(2) . . . . ?
N2 C17 C18 C19 -0.3(2) . . . . ?
N2 C17 C22 C23 41.5(3) . . . . ?
N2 C17 C22 C27 -140.4(2) . . . . ?
N2 C20 C21 C14 8.4(3) . . . . ?
N2 C20 C21 N1 -176.64(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
####################################################################### 
# 
# 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_11_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2498971'
loop_
_audit_author_name
_audit_author_address
chenkairong
;shiheziuniversity
China
;
_audit_update_record             
;
2025-10-30 deposited with the CCDC.	2026-03-10 downloaded from the CCDC.
;
_audit_creation_date             2025-05-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        
11-(4-Fluorobenzyl)-3-(4-fluorophenyl)-5,6-dihydroindolizino[8,7-b]indole
_chemical_formula_moiety         'C27 H20 F2 N2'
_chemical_formula_sum            'C27 H20 F2 N2'
_chemical_formula_weight         410.45
_chemical_melting_point          187.8-189.6
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   14.6398(13)
_cell_length_b                   9.8340(9)
_cell_length_c                   27.715(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3990.1(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3695
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      71.26
_cell_measurement_theta_min      3.19
_shelx_estimated_absorpt_T_max   0.901
_shelx_estimated_absorpt_T_min   0.882
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1141 before and 0.0785 after correction.
The Ratio of minimum to maximum transmission is 0.8429.
The λ/2 correction factor is Not present.
;
_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    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1172
_diffrn_reflns_av_unetI/netI     0.0755
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18150
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.077
_diffrn_reflns_theta_min         3.189
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_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                2504
_reflns_number_total             3867
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0018(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3867
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1182
_refine_ls_R_factor_gt           0.0750
_refine_ls_restrained_S_all      1.057
_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)+(0.0729P)²+2.6084P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1697
_refine_ls_wR_factor_ref         0.1940
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C15(H15A,H15B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
 C18(H18), C19(H19), C23(H23), C24(H24), C26(H26), C27(H27)
;
_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
C1 C 0.2105(2) 0.3361(4) 0.65618(13) 0.0436(8) Uani 1 1 d . . . . .
H1A H 0.177718 0.258311 0.670835 0.052 Uiso 1 1 calc R U . . .
H1B H 0.242368 0.302175 0.627068 0.052 Uiso 1 1 calc R U . . .
C2 C 0.1414(2) 0.4415(4) 0.64101(12) 0.0385(8) Uani 1 1 d . . . . .
C3 C 0.0901(2) 0.4219(4) 0.59935(13) 0.0466(9) Uani 1 1 d . . . . .
H3 H 0.098201 0.341214 0.580976 0.056 Uiso 1 1 calc R U . . .
C4 C 0.0274(2) 0.5184(4) 0.58433(13) 0.0485(9) Uani 1 1 d . . . . .
H4 H -0.006576 0.506004 0.555475 0.058 Uiso 1 1 calc R U . . .
C5 C 0.0157(2) 0.6322(4) 0.61207(14) 0.0459(9) Uani 1 1 d . . . . .
C6 C 0.0641(2) 0.6553(4) 0.65382(13) 0.0451(8) Uani 1 1 d . . . . .
H6 H 0.054074 0.734924 0.672522 0.054 Uiso 1 1 calc R U . . .
C7 C 0.1277(2) 0.5592(4) 0.66771(12) 0.0414(8) Uani 1 1 d . . . . .
H7 H 0.162760 0.573879 0.696084 0.050 Uiso 1 1 calc R U . . .
C8 C 0.2794(2) 0.3594(4) 0.73946(12) 0.0391(8) Uani 1 1 d . . . . .
C9 C 0.2188(2) 0.2843(4) 0.76766(14) 0.0475(9) Uani 1 1 d . . . . .
H9 H 0.166296 0.242681 0.753921 0.057 Uiso 1 1 calc R U . . .
C10 C 0.2377(2) 0.2726(4) 0.81606(14) 0.0502(9) Uani 1 1 d . . . . .
H10 H 0.197322 0.222405 0.836130 0.060 Uiso 1 1 calc R U . . .
C11 C 0.3154(2) 0.3333(4) 0.83647(13) 0.0472(9) Uani 1 1 d . . . . .
H11 H 0.326619 0.323246 0.870039 0.057 Uiso 1 1 calc R U . . .
C12 C 0.3756(2) 0.4073(4) 0.80867(12) 0.0422(8) Uani 1 1 d . . . . .
H12 H 0.427879 0.448281 0.822881 0.051 Uiso 1 1 calc R U . . .
C13 C 0.3586(2) 0.4212(3) 0.75893(12) 0.0380(7) Uani 1 1 d . . . . .
C14 C 0.4049(2) 0.4860(4) 0.72001(11) 0.0375(8) Uani 1 1 d . . . . .
C15 C 0.4934(2) 0.5626(4) 0.71690(11) 0.0425(8) Uani 1 1 d . . . . .
H15A H 0.533559 0.536651 0.744142 0.051 Uiso 1 1 calc R U . . .
H15B H 0.481594 0.661569 0.718985 0.051 Uiso 1 1 calc R U . . .
C16 C 0.5404(2) 0.5296(4) 0.66925(11) 0.0414(8) Uani 1 1 d . . . . .
H16A H 0.591543 0.593872 0.664181 0.050 Uiso 1 1 calc R U . . .
H16B H 0.566138 0.436697 0.670897 0.050 Uiso 1 1 calc R U . . .
C17 C 0.4970(2) 0.5698(4) 0.58097(11) 0.0412(8) Uani 1 1 d . . . . .
C18 C 0.4168(2) 0.5580(4) 0.55507(13) 0.0474(9) Uani 1 1 d . . . . .
H18 H 0.409612 0.575707 0.521592 0.057 Uiso 1 1 calc R U . . .
C19 C 0.3478(2) 0.5153(4) 0.58678(12) 0.0447(9) Uani 1 1 d . . . . .
H19 H 0.285759 0.498700 0.578562 0.054 Uiso 1 1 calc R U . . .
C20 C 0.3859(2) 0.5016(4) 0.63180(12) 0.0391(8) Uani 1 1 d . . . . .
C21 C 0.3551(2) 0.4619(4) 0.67899(12) 0.0368(7) Uani 1 1 d . . . . .
C22 C 0.5882(2) 0.6054(4) 0.56335(12) 0.0439(8) Uani 1 1 d . . . . .
C23 C 0.6666(2) 0.5357(4) 0.57792(12) 0.0456(9) Uani 1 1 d . . . . .
H23 H 0.661507 0.464829 0.601041 0.055 Uiso 1 1 calc R U . . .
C24 C 0.7520(3) 0.5683(5) 0.55921(13) 0.0563(10) Uani 1 1 d . . . . .
H24 H 0.805276 0.521971 0.569816 0.068 Uiso 1 1 calc R U . . .
C25 C 0.7572(3) 0.6682(5) 0.52530(14) 0.0635(12) Uani 1 1 d . . . . .
C26 C 0.6827(3) 0.7382(5) 0.50872(14) 0.0661(13) Uani 1 1 d . . . . .
H26 H 0.688736 0.806212 0.484571 0.079 Uiso 1 1 calc R U . . .
C27 C 0.5976(3) 0.7068(4) 0.52835(14) 0.0592(11) Uani 1 1 d . . . . .
H27 H 0.545096 0.755065 0.517756 0.071 Uiso 1 1 calc R U . . .
F1 F -0.04650(15) 0.7275(3) 0.59741(9) 0.0654(7) Uani 1 1 d . . . . .
F2 F 0.84115(19) 0.6967(3) 0.50606(10) 0.0914(10) Uani 1 1 d . . . . .
N1 N 0.27822(17) 0.3851(3) 0.69028(10) 0.0398(7) Uani 1 1 d . . . . .
N2 N 0.47756(18) 0.5382(3) 0.62821(9) 0.0376(6) 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
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.508(5) . ?
C1 N1 1.452(4) . ?
C2 C3 1.391(4) . ?
C2 C7 1.388(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.368(5) . ?
C5 C6 1.376(5) . ?
C5 F1 1.368(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.382(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.394(5) . ?
C8 C13 1.416(4) . ?
C8 N1 1.386(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.375(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.403(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.379(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.408(4) . ?
C13 C14 1.424(5) . ?
C14 C15 1.502(4) . ?
C14 C21 1.371(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.524(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 N2 1.465(4) . ?
C17 C18 1.380(5) . ?
C17 C22 1.464(5) . ?
C17 N2 1.375(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.404(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.373(4) . ?
C20 C21 1.437(4) . ?
C20 N2 1.393(4) . ?
C21 N1 1.391(4) . ?
C22 C23 1.396(5) . ?
C22 C27 1.398(5) . ?
C23 H23 0.9500 . ?
C23 C24 1.391(5) . ?
C24 H24 0.9500 . ?
C24 C25 1.362(6) . ?
C25 C26 1.370(7) . ?
C25 F2 1.368(4) . ?
C26 H26 0.9500 . ?
C26 C27 1.394(6) . ?
C27 H27 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
H1A C1 H1B 107.6 . . ?
C2 C1 H1A 108.7 . . ?
C2 C1 H1B 108.7 . . ?
N1 C1 H1A 108.7 . . ?
N1 C1 H1B 108.7 . . ?
N1 C1 C2 114.3(3) . . ?
C3 C2 C1 119.9(3) . . ?
C7 C2 C1 121.4(3) . . ?
C7 C2 C3 118.7(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.8 . . ?
C5 C4 C3 118.4(3) . . ?
C5 C4 H4 120.8 . . ?
C4 C5 C6 122.9(3) . . ?
F1 C5 C4 118.5(3) . . ?
F1 C5 C6 118.6(3) . . ?
C5 C6 H6 121.0 . . ?
C5 C6 C7 117.9(4) . . ?
C7 C6 H6 121.0 . . ?
C2 C7 H7 119.4 . . ?
C6 C7 C2 121.3(3) . . ?
C6 C7 H7 119.4 . . ?
C9 C8 C13 122.4(3) . . ?
N1 C8 C9 129.8(3) . . ?
N1 C8 C13 107.9(3) . . ?
C8 C9 H9 121.2 . . ?
C10 C9 C8 117.6(3) . . ?
C10 C9 H9 121.2 . . ?
C9 C10 H10 119.3 . . ?
C9 C10 C11 121.4(3) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.2(3) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 120.5 . . ?
C11 C12 C13 119.0(3) . . ?
C13 C12 H12 120.5 . . ?
C8 C13 C14 107.1(3) . . ?
C12 C13 C8 118.4(3) . . ?
C12 C13 C14 134.5(3) . . ?
C13 C14 C15 132.7(3) . . ?
C21 C14 C13 107.3(3) . . ?
C21 C14 C15 119.9(3) . . ?
C14 C15 H15A 109.8 . . ?
C14 C15 H15B 109.8 . . ?
C14 C15 C16 109.4(3) . . ?
H15A C15 H15B 108.2 . . ?
C16 C15 H15A 109.8 . . ?
C16 C15 H15B 109.8 . . ?
C15 C16 H16A 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
N2 C16 C15 112.2(3) . . ?
N2 C16 H16A 109.2 . . ?
N2 C16 H16B 109.2 . . ?
C18 C17 C22 128.5(3) . . ?
N2 C17 C18 107.5(3) . . ?
N2 C17 C22 124.0(3) . . ?
C17 C18 H18 125.9 . . ?
C17 C18 C19 108.2(3) . . ?
C19 C18 H18 125.9 . . ?
C18 C19 H19 126.1 . . ?
C20 C19 C18 107.8(3) . . ?
C20 C19 H19 126.1 . . ?
C19 C20 C21 136.6(3) . . ?
C19 C20 N2 107.5(3) . . ?
N2 C20 C21 115.9(3) . . ?
C14 C21 C20 122.7(3) . . ?
C14 C21 N1 109.8(3) . . ?
N1 C21 C20 127.3(3) . . ?
C23 C22 C17 122.4(3) . . ?
C23 C22 C27 118.0(4) . . ?
C27 C22 C17 119.4(4) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 C22 121.2(4) . . ?
C24 C23 H23 119.4 . . ?
C23 C24 H24 120.8 . . ?
C25 C24 C23 118.3(4) . . ?
C25 C24 H24 120.8 . . ?
C24 C25 C26 123.3(4) . . ?
C24 C25 F2 117.9(5) . . ?
F2 C25 C26 118.8(4) . . ?
C25 C26 H26 121.0 . . ?
C25 C26 C27 118.0(4) . . ?
C27 C26 H26 121.0 . . ?
C22 C27 H27 119.4 . . ?
C26 C27 C22 121.2(4) . . ?
C26 C27 H27 119.4 . . ?
C8 N1 C1 126.0(3) . . ?
C8 N1 C21 108.0(3) . . ?
C21 N1 C1 125.9(3) . . ?
C17 N2 C16 128.5(3) . . ?
C17 N2 C20 109.0(3) . . ?
C20 N2 C16 122.3(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -178.9(3) . . . . ?
C1 C2 C7 C6 -179.7(3) . . . . ?
C2 C1 N1 C8 103.0(4) . . . . ?
C2 C1 N1 C21 -79.5(4) . . . . ?
C2 C3 C4 C5 -1.5(6) . . . . ?
C3 C2 C7 C6 0.5(5) . . . . ?
C3 C4 C5 C6 0.7(6) . . . . ?
C3 C4 C5 F1 -179.7(3) . . . . ?
C4 C5 C6 C7 0.6(6) . . . . ?
C5 C6 C7 C2 -1.2(5) . . . . ?
C7 C2 C3 C4 0.9(5) . . . . ?
C8 C9 C10 C11 -0.3(6) . . . . ?
C8 C13 C14 C15 -177.2(4) . . . . ?
C8 C13 C14 C21 -0.6(4) . . . . ?
C9 C8 C13 C12 -0.8(5) . . . . ?
C9 C8 C13 C14 178.7(3) . . . . ?
C9 C8 N1 C1 -0.3(6) . . . . ?
C9 C8 N1 C21 -178.2(4) . . . . ?
C9 C10 C11 C12 0.1(6) . . . . ?
C10 C11 C12 C13 -0.3(6) . . . . ?
C11 C12 C13 C8 0.6(5) . . . . ?
C11 C12 C13 C14 -178.8(4) . . . . ?
C12 C13 C14 C15 2.2(7) . . . . ?
C12 C13 C14 C21 178.8(4) . . . . ?
C13 C8 C9 C10 0.7(5) . . . . ?
C13 C8 N1 C1 177.7(3) . . . . ?
C13 C8 N1 C21 -0.2(4) . . . . ?
C13 C14 C15 C16 142.6(4) . . . . ?
C13 C14 C21 C20 -174.2(3) . . . . ?
C13 C14 C21 N1 0.5(4) . . . . ?
C14 C15 C16 N2 47.2(4) . . . . ?
C14 C21 N1 C1 -178.1(3) . . . . ?
C14 C21 N1 C8 -0.2(4) . . . . ?
C15 C14 C21 C20 2.9(5) . . . . ?
C15 C14 C21 N1 177.6(3) . . . . ?
C15 C16 N2 C17 151.2(3) . . . . ?
C15 C16 N2 C20 -34.7(4) . . . . ?
C17 C18 C19 C20 0.2(4) . . . . ?
C17 C22 C23 C24 177.5(3) . . . . ?
C17 C22 C27 C26 -176.4(3) . . . . ?
C18 C17 C22 C23 -135.9(4) . . . . ?
C18 C17 C22 C27 40.0(6) . . . . ?
C18 C17 N2 C16 176.8(3) . . . . ?
C18 C17 N2 C20 2.1(4) . . . . ?
C18 C19 C20 C21 -179.4(4) . . . . ?
C18 C19 C20 N2 1.1(4) . . . . ?
C19 C20 C21 C14 -165.4(4) . . . . ?
C19 C20 C21 N1 20.9(7) . . . . ?
C19 C20 N2 C16 -177.1(3) . . . . ?
C19 C20 N2 C17 -2.0(4) . . . . ?
C20 C21 N1 C1 -3.7(5) . . . . ?
C20 C21 N1 C8 174.2(3) . . . . ?
C21 C14 C15 C16 -33.6(5) . . . . ?
C21 C20 N2 C16 3.3(5) . . . . ?
C21 C20 N2 C17 178.4(3) . . . . ?
C22 C17 C18 C19 177.0(4) . . . . ?
C22 C17 N2 C16 -1.7(6) . . . . ?
C22 C17 N2 C20 -176.4(3) . . . . ?
C22 C23 C24 C25 -1.5(6) . . . . ?
C23 C22 C27 C26 -0.4(6) . . . . ?
C23 C24 C25 C26 0.0(7) . . . . ?
C23 C24 C25 F2 -178.1(3) . . . . ?
C24 C25 C26 C27 1.2(7) . . . . ?
C25 C26 C27 C22 -1.0(6) . . . . ?
C27 C22 C23 C24 1.6(5) . . . . ?
F1 C5 C6 C7 -178.9(3) . . . . ?
F2 C25 C26 C27 179.3(4) . . . . ?
N1 C1 C2 C3 161.7(3) . . . . ?
N1 C1 C2 C7 -18.1(5) . . . . ?
N1 C8 C9 C10 178.5(3) . . . . ?
N1 C8 C13 C12 -179.1(3) . . . . ?
N1 C8 C13 C14 0.5(4) . . . . ?
N2 C17 C18 C19 -1.4(4) . . . . ?
N2 C17 C22 C23 42.4(5) . . . . ?
N2 C17 C22 C27 -141.8(4) . . . . ?
N2 C20 C21 C14 14.0(5) . . . . ?
N2 C20 C21 N1 -159.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
