# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 2322747'
loop_
_audit_author_name
_audit_author_address
'Yi Jin'
;Yunnan University
China
;
_audit_update_record             
;
2023-12-31 deposited with the CCDC.	2024-03-22 downloaded from the CCDC.
;
_audit_creation_date             2023-07-17
_diffrn_source_power             0.07
_audit_creation_method           
;
FinalCif V88 by Daniel Kratzert, Freiburg 2023,
https://github.com/dkratzert/FinalCif
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C20 H16 N4'
_chemical_formula_moiety         'C20 H16 N4'
_exptl_crystal_colour_primary    colourless
_chemical_formula_weight         312.37
_chemical_melting_point          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C5, C4
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.001
 C8, C9
 with sigma for 1-2 distances of 0.0005 and sigma for 1-3 distances of 0.0001
3.a Ternary CH refined with riding coordinates:
 C12(H12), C32(H32)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C15(H15),
 C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C26(H26),
  C27(H27), C28(H28), C29(H29), C35(H35), C36(H36), C37(H37), C38(H38)
3.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C33(H33A,H33B,H33C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+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                   8.6995(4)
_cell_length_b                   18.4071(7)
_cell_length_c                   39.8272(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6377.6(4)
_cell_formula_units_Z            16
_cell_measurement_temperature    100.00
_cell_measurement_reflns_used    9379
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      27.36
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_F_000             2624
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7000
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0983 before and 0.0614 after correction.
The Ratio of minimum to maximum transmission is 0.9387.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.986
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100.00
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.4
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            48204
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_av_R_equivalents  0.0723
_diffrn_reflns_theta_min         2.045
_diffrn_reflns_theta_max         28.323
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_limit_l_max       51
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7935
_reflns_number_gt                5104
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       
'Bruker BIS V6.2.16/2021-10-22 && APEX4 2022.1-1'
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0446P)²+1.8120P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         7935
_refine_ls_number_parameters     436
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0973
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1198
_refine_ls_wR_factor_gt          0.0995
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00238(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^

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'

_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_
_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 0.42058(16) 0.42992(7) 0.31925(3) 0.0262(3) Uani 1 1 d . . . . .
N2 N 0.40485(16) 0.38037(7) 0.37413(3) 0.0218(3) Uani 1 1 d . . . . .
N3 N 0.40991(16) 0.31020(7) 0.38489(3) 0.0251(3) Uani 1 1 d . . . . .
N4 N 0.49968(17) 0.30671(7) 0.41119(3) 0.0255(3) Uani 1 1 d . . . . .
C00K C 0.4212(2) 0.50053(9) 0.30680(4) 0.0274(4) Uani 1 1 d . . . . .
C1 C 0.5400(2) 0.39078(10) 0.30416(4) 0.0279(4) Uani 1 1 d . . . . .
C2 C 0.5879(2) 0.31969(10) 0.30932(4) 0.0314(4) Uani 1 1 d . . . . .
H2 H 0.537299 0.289133 0.325048 0.038 Uiso 1 1 calc R U . . .
C3 C 0.7119(2) 0.29480(12) 0.29075(4) 0.0403(5) Uani 1 1 d . . . . .
H3 H 0.745863 0.246169 0.293705 0.048 Uiso 1 1 calc R U . . .
C4 C 0.7878(2) 0.33923(12) 0.26790(5) 0.0455(5) Uani 1 1 d . U . . .
H4 H 0.872889 0.320711 0.255627 0.055 Uiso 1 1 calc R U . . .
C5 C 0.7408(2) 0.40979(12) 0.26290(4) 0.0423(5) Uani 1 1 d . U . . .
H5 H 0.792845 0.439972 0.247241 0.051 Uiso 1 1 calc R U . . .
C6 C 0.6156(2) 0.43664(10) 0.28113(4) 0.0311(4) Uani 1 1 d . . . . .
C7 C 0.5408(2) 0.50640(10) 0.28285(4) 0.0315(4) Uani 1 1 d . . . . .
C8 C 0.5641(3) 0.57261(11) 0.26669(5) 0.0431(5) Uani 1 1 d . U . . .
H8 H 0.643807 0.577783 0.250566 0.052 Uiso 1 1 calc R U . . .
C9 C 0.4703(3) 0.63041(11) 0.27436(5) 0.0456(5) Uani 1 1 d . U . . .
H9 H 0.486218 0.675708 0.263473 0.055 Uiso 1 1 calc R U . . .
C10 C 0.3511(3) 0.62366(10) 0.29804(5) 0.0410(5) Uani 1 1 d . . . . .
H10 H 0.287814 0.664417 0.302839 0.049 Uiso 1 1 calc R U . . .
C11 C 0.3246(2) 0.55830(10) 0.31451(4) 0.0326(4) Uani 1 1 d . . . . .
H11 H 0.243747 0.553317 0.330389 0.039 Uiso 1 1 calc R U . . .
C12 C 0.31604(19) 0.40275(9) 0.34471(4) 0.0246(4) Uani 1 1 d . . . . .
H12 H 0.248783 0.444110 0.351723 0.030 Uiso 1 1 calc R U . . .
C13 C 0.2120(2) 0.34276(10) 0.33181(4) 0.0319(4) Uani 1 1 d . . . . .
H13A H 0.148546 0.361471 0.313408 0.048 Uiso 1 1 calc R U . . .
H13B H 0.145404 0.325813 0.350048 0.048 Uiso 1 1 calc R U . . .
H13C H 0.274808 0.302251 0.323646 0.048 Uiso 1 1 calc R U . . .
C14 C 0.49570(19) 0.42312(8) 0.39391(4) 0.0207(3) Uani 1 1 d . . . . .
C15 C 0.5317(2) 0.49705(9) 0.39334(4) 0.0245(4) Uani 1 1 d . . . . .
H15 H 0.489054 0.529271 0.377204 0.029 Uiso 1 1 calc R U . . .
C16 C 0.6327(2) 0.52024(9) 0.41762(4) 0.0272(4) Uani 1 1 d . . . . .
H16 H 0.661992 0.569954 0.418058 0.033 Uiso 1 1 calc R U . . .
C17 C 0.6943(2) 0.47275(9) 0.44187(4) 0.0279(4) Uani 1 1 d . . . . .
H17 H 0.763669 0.491351 0.458164 0.033 Uiso 1 1 calc R U . . .
C18 C 0.6567(2) 0.40007(9) 0.44261(4) 0.0265(4) Uani 1 1 d . . . . .
H18 H 0.697119 0.368247 0.459185 0.032 Uiso 1 1 calc R U . . .
C19 C 0.55602(19) 0.37557(9) 0.41772(4) 0.0232(4) Uani 1 1 d . . . . .
N5 N 0.12747(16) 0.57956(7) 0.42355(3) 0.0212(3) Uani 1 1 d . . . . .
N6 N 0.29337(16) 0.66906(7) 0.44714(3) 0.0220(3) Uani 1 1 d . . . . .
N7 N 0.35362(18) 0.67459(7) 0.47865(3) 0.0277(3) Uani 1 1 d . . . . .
N8 N 0.49727(18) 0.69502(7) 0.47639(4) 0.0291(3) Uani 1 1 d . . . . .
C20 C -0.0139(2) 0.61884(10) 0.37145(4) 0.0309(4) Uani 1 1 d . . . . .
H20 H 0.002110 0.669426 0.374610 0.037 Uiso 1 1 calc R U . . .
C21 C -0.0934(2) 0.59269(11) 0.34383(5) 0.0404(5) Uani 1 1 d . . . . .
H21 H -0.131771 0.626009 0.327653 0.048 Uiso 1 1 calc R U . . .
C22 C -0.1182(2) 0.51877(11) 0.33928(5) 0.0431(5) Uani 1 1 d . . . . .
H22 H -0.172924 0.502498 0.320056 0.052 Uiso 1 1 calc R U . . .
C23 C -0.0646(2) 0.46848(11) 0.36226(5) 0.0358(5) Uani 1 1 d . . . . .
H23 H -0.083543 0.418112 0.359123 0.043 Uiso 1 1 calc R U . . .
C24 C 0.01792(19) 0.49291(9) 0.39017(4) 0.0256(4) Uani 1 1 d . . . . .
C25 C 0.09330(19) 0.45728(9) 0.41801(4) 0.0240(4) Uani 1 1 d . . . . .
C26 C 0.1117(2) 0.38433(9) 0.42723(4) 0.0294(4) Uani 1 1 d . . . . .
H26 H 0.065422 0.346704 0.414409 0.035 Uiso 1 1 calc R U . . .
C27 C 0.1981(2) 0.36819(9) 0.45518(4) 0.0311(4) Uani 1 1 d . . . . .
H27 H 0.211306 0.318900 0.461630 0.037 Uiso 1 1 calc R U . . .
C28 C 0.2667(2) 0.42307(9) 0.47428(4) 0.0281(4) Uani 1 1 d . . . . .
H28 H 0.327236 0.410330 0.493236 0.034 Uiso 1 1 calc R U . . .
C29 C 0.2481(2) 0.49569(9) 0.46607(4) 0.0239(4) Uani 1 1 d . . . . .
H29 H 0.293467 0.533038 0.479213 0.029 Uiso 1 1 calc R U . . .
C30 C 0.16033(19) 0.51179(8) 0.43784(4) 0.0207(3) Uani 1 1 d . . . . .
C31 C 0.04145(19) 0.56817(9) 0.39439(4) 0.0236(4) Uani 1 1 d . . . . .
C32 C 0.13321(19) 0.64864(8) 0.44106(4) 0.0223(4) Uani 1 1 d . . . . .
H32 H 0.088329 0.686039 0.425717 0.027 Uiso 1 1 calc R U . . .
C33 C 0.0386(2) 0.64939(9) 0.47311(4) 0.0290(4) Uani 1 1 d . . . . .
H33A H -0.068468 0.637471 0.467846 0.044 Uiso 1 1 calc R U . . .
H33B H 0.043529 0.697777 0.483314 0.044 Uiso 1 1 calc R U . . .
H33C H 0.079852 0.613393 0.488849 0.044 Uiso 1 1 calc R U . . .
C34 C 0.40240(19) 0.68574(8) 0.42394(4) 0.0216(3) Uani 1 1 d . . . . .
C35 C 0.4018(2) 0.68747(9) 0.38881(4) 0.0247(4) Uani 1 1 d . . . . .
H35 H 0.313304 0.674966 0.376090 0.030 Uiso 1 1 calc R U . . .
C36 C 0.5373(2) 0.70838(9) 0.37384(4) 0.0295(4) Uani 1 1 d . . . . .
H36 H 0.542827 0.709658 0.350025 0.035 Uiso 1 1 calc R U . . .
C37 C 0.6680(2) 0.72796(9) 0.39265(5) 0.0316(4) Uani 1 1 d . . . . .
H37 H 0.758038 0.743398 0.381205 0.038 Uiso 1 1 calc R U . . .
C38 C 0.6686(2) 0.72529(9) 0.42717(5) 0.0302(4) Uani 1 1 d . . . . .
H38 H 0.757340 0.737914 0.439794 0.036 Uiso 1 1 calc R U . . .
C39 C 0.5326(2) 0.70315(8) 0.44278(4) 0.0251(4) Uani 1 1 d . . . . .


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 C00K 1.391(2) . ?
N1 C1 1.400(2) . ?
N1 C12 1.451(2) . ?
N2 N3 1.3617(18) . ?
N2 C12 1.463(2) . ?
N2 C14 1.366(2) . ?
N3 N4 1.3083(19) . ?
N4 C19 1.384(2) . ?
C00K C7 1.416(2) . ?
C00K C11 1.390(3) . ?
C1 C2 1.388(3) . ?
C1 C6 1.409(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.386(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.376(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.399(3) . ?
C6 C7 1.441(3) . ?
C7 C8 1.393(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.375(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.407(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(2) . ?
C11 H11 0.9500 . ?
C12 H12 1.0000 . ?
C12 C13 1.517(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.397(2) . ?
C14 C19 1.393(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.375(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.409(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.378(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.398(2) . ?
N5 C30 1.4006(19) . ?
N5 C31 1.397(2) . ?
N5 C32 1.4512(19) . ?
N6 N7 1.3640(17) . ?
N6 C32 1.463(2) . ?
N6 C34 1.359(2) . ?
N7 N8 1.308(2) . ?
N8 C39 1.381(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.386(2) . ?
C20 C31 1.392(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.390(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.383(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.398(2) . ?
C24 C25 1.446(2) . ?
C24 C31 1.410(2) . ?
C25 C26 1.401(2) . ?
C25 C30 1.404(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.375(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.398(2) . ?
C28 H28 0.9500 . ?
C28 C29 1.386(2) . ?
C29 H29 0.9500 . ?
C29 C30 1.391(2) . ?
C32 H32 1.0000 . ?
C32 C33 1.518(2) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 C35 1.399(2) . ?
C34 C39 1.396(2) . ?
C35 H35 0.9500 . ?
C35 C36 1.376(2) . ?
C36 H36 0.9500 . ?
C36 C37 1.409(2) . ?
C37 H37 0.9500 . ?
C37 C38 1.375(2) . ?
C38 H38 0.9500 . ?
C38 C39 1.398(3) . ?

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
C00K N1 C1 108.97(14) . . ?
C00K N1 C12 124.99(15) . . ?
C1 N1 C12 126.01(14) . . ?
N3 N2 C12 122.43(13) . . ?
N3 N2 C14 110.26(13) . . ?
C14 N2 C12 127.28(13) . . ?
N4 N3 N2 108.53(13) . . ?
N3 N4 C19 108.48(13) . . ?
N1 C00K C7 108.31(16) . . ?
C11 C00K N1 129.33(16) . . ?
C11 C00K C7 122.35(16) . . ?
N1 C1 C6 108.51(16) . . ?
C2 C1 N1 130.09(15) . . ?
C2 C1 C6 121.38(17) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 C1 117.78(17) . . ?
C3 C2 H2 121.1 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.6(2) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.56(19) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.32(18) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C7 106.99(16) . . ?
C5 C6 C1 119.31(18) . . ?
C5 C6 C7 133.68(17) . . ?
C00K C7 C6 107.20(15) . . ?
C8 C7 C00K 119.00(19) . . ?
C8 C7 C6 133.80(18) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 C7 119.2(2) . . ?
C9 C8 H8 120.4 . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.19(19) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.0(2) . . ?
C11 C10 H10 119.5 . . ?
C00K C11 H11 121.4 . . ?
C10 C11 C00K 117.23(18) . . ?
C10 C11 H11 121.4 . . ?
N1 C12 N2 109.00(13) . . ?
N1 C12 H12 107.4 . . ?
N1 C12 C13 112.85(13) . . ?
N2 C12 H12 107.4 . . ?
N2 C12 C13 112.42(13) . . ?
C13 C12 H12 107.4 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 C15 132.99(15) . . ?
N2 C14 C19 104.40(14) . . ?
C19 C14 C15 122.60(15) . . ?
C14 C15 H15 122.1 . . ?
C16 C15 C14 115.76(15) . . ?
C16 C15 H15 122.1 . . ?
C15 C16 H16 118.9 . . ?
C15 C16 C17 122.19(16) . . ?
C17 C16 H16 118.9 . . ?
C16 C17 H17 119.1 . . ?
C18 C17 C16 121.81(16) . . ?
C18 C17 H17 119.1 . . ?
C17 C18 H18 121.7 . . ?
C17 C18 C19 116.55(15) . . ?
C19 C18 H18 121.7 . . ?
N4 C19 C14 108.31(14) . . ?
N4 C19 C18 130.61(15) . . ?
C14 C19 C18 121.07(15) . . ?
C30 N5 C32 125.31(13) . . ?
C31 N5 C30 108.27(13) . . ?
C31 N5 C32 123.32(13) . . ?
N7 N6 C32 122.49(13) . . ?
C34 N6 N7 109.91(13) . . ?
C34 N6 C32 127.60(13) . . ?
N8 N7 N6 108.98(13) . . ?
N7 N8 C39 108.08(14) . . ?
C21 C20 H20 121.3 . . ?
C21 C20 C31 117.47(17) . . ?
C31 C20 H20 121.3 . . ?
C20 C21 H21 119.3 . . ?
C20 C21 C22 121.40(18) . . ?
C22 C21 H21 119.3 . . ?
C21 C22 H22 119.4 . . ?
C23 C22 C21 121.12(17) . . ?
C23 C22 H22 119.4 . . ?
C22 C23 H23 120.5 . . ?
C22 C23 C24 118.97(17) . . ?
C24 C23 H23 120.5 . . ?
C23 C24 C25 134.20(16) . . ?
C23 C24 C31 119.03(17) . . ?
C31 C24 C25 106.76(14) . . ?
C26 C25 C24 133.44(16) . . ?
C26 C25 C30 119.34(16) . . ?
C30 C25 C24 107.20(14) . . ?
C25 C26 H26 120.6 . . ?
C27 C26 C25 118.78(16) . . ?
C27 C26 H26 120.6 . . ?
C26 C27 H27 119.4 . . ?
C26 C27 C28 121.16(16) . . ?
C28 C27 H27 119.4 . . ?
C27 C28 H28 119.4 . . ?
C29 C28 C27 121.24(16) . . ?
C29 C28 H28 119.4 . . ?
C28 C29 H29 121.3 . . ?
C28 C29 C30 117.41(16) . . ?
C30 C29 H29 121.3 . . ?
N5 C30 C25 108.85(14) . . ?
C29 C30 N5 129.07(14) . . ?
C29 C30 C25 122.04(15) . . ?
N5 C31 C24 108.91(14) . . ?
C20 C31 N5 129.09(15) . . ?
C20 C31 C24 121.99(15) . . ?
N5 C32 N6 109.71(13) . . ?
N5 C32 H32 107.2 . . ?
N5 C32 C33 113.16(13) . . ?
N6 C32 H32 107.2 . . ?
N6 C32 C33 112.00(13) . . ?
C33 C32 H32 107.2 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
N6 C34 C35 133.01(16) . . ?
N6 C34 C39 104.63(14) . . ?
C39 C34 C35 122.36(16) . . ?
C34 C35 H35 122.1 . . ?
C36 C35 C34 115.89(16) . . ?
C36 C35 H35 122.1 . . ?
C35 C36 H36 118.9 . . ?
C35 C36 C37 122.17(17) . . ?
C37 C36 H36 118.9 . . ?
C36 C37 H37 119.1 . . ?
C38 C37 C36 121.72(17) . . ?
C38 C37 H37 119.1 . . ?
C37 C38 H38 121.6 . . ?
C37 C38 C39 116.85(17) . . ?
C39 C38 H38 121.6 . . ?
N8 C39 C34 108.40(15) . . ?
N8 C39 C38 130.63(16) . . ?
C34 C39 C38 120.97(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
N1 C00K C7 C6 -0.50(18) . . . . ?
N1 C00K C7 C8 179.83(15) . . . . ?
N1 C00K C11 C10 -179.80(16) . . . . ?
N1 C1 C2 C3 -179.61(17) . . . . ?
N1 C1 C6 C5 179.58(15) . . . . ?
N1 C1 C6 C7 1.07(18) . . . . ?
N2 N3 N4 C19 -0.57(17) . . . . ?
N2 C14 C15 C16 -178.55(16) . . . . ?
N2 C14 C19 N4 0.22(17) . . . . ?
N2 C14 C19 C18 179.71(14) . . . . ?
N3 N2 C12 N1 -116.18(15) . . . . ?
N3 N2 C12 C13 9.7(2) . . . . ?
N3 N2 C14 C15 178.89(17) . . . . ?
N3 N2 C14 C19 -0.57(17) . . . . ?
N3 N4 C19 C14 0.22(18) . . . . ?
N3 N4 C19 C18 -179.21(16) . . . . ?
C00K N1 C1 C2 177.60(17) . . . . ?
C00K N1 C1 C6 -1.41(18) . . . . ?
C00K N1 C12 N2 -117.70(16) . . . . ?
C00K N1 C12 C13 116.66(17) . . . . ?
C00K C7 C8 C9 -0.1(3) . . . . ?
C1 N1 C00K C7 1.18(18) . . . . ?
C1 N1 C00K C11 -179.89(16) . . . . ?
C1 N1 C12 N2 59.8(2) . . . . ?
C1 N1 C12 C13 -65.8(2) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C1 C6 C7 C00K -0.35(18) . . . . ?
C1 C6 C7 C8 179.25(19) . . . . ?
C2 C1 C6 C5 0.5(3) . . . . ?
C2 C1 C6 C7 -178.04(16) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C4 C5 C6 C7 177.87(19) . . . . ?
C5 C6 C7 C00K -178.56(19) . . . . ?
C5 C6 C7 C8 1.0(3) . . . . ?
C6 C1 C2 C3 -0.7(3) . . . . ?
C6 C7 C8 C9 -179.68(18) . . . . ?
C7 C00K C11 C10 -1.0(2) . . . . ?
C7 C8 C9 C10 -0.3(3) . . . . ?
C8 C9 C10 C11 0.1(3) . . . . ?
C9 C10 C11 C00K 0.5(3) . . . . ?
C11 C00K C7 C6 -179.52(15) . . . . ?
C11 C00K C7 C8 0.8(2) . . . . ?
C12 N1 C00K C7 179.07(14) . . . . ?
C12 N1 C00K C11 -2.0(3) . . . . ?
C12 N1 C1 C2 -0.3(3) . . . . ?
C12 N1 C1 C6 -179.27(15) . . . . ?
C12 N2 N3 N4 179.02(13) . . . . ?
C12 N2 C14 C15 0.7(3) . . . . ?
C12 N2 C14 C19 -178.76(14) . . . . ?
C14 N2 N3 N4 0.73(17) . . . . ?
C14 N2 C12 N1 61.8(2) . . . . ?
C14 N2 C12 C13 -172.30(15) . . . . ?
C14 C15 C16 C17 -0.9(2) . . . . ?
C15 C14 C19 N4 -179.32(14) . . . . ?
C15 C14 C19 C18 0.2(2) . . . . ?
C15 C16 C17 C18 0.1(3) . . . . ?
C16 C17 C18 C19 1.0(2) . . . . ?
C17 C18 C19 N4 178.30(16) . . . . ?
C17 C18 C19 C14 -1.1(2) . . . . ?
C19 C14 C15 C16 0.8(2) . . . . ?
N6 N7 N8 C39 0.01(17) . . . . ?
N6 C34 C35 C36 179.27(16) . . . . ?
N6 C34 C39 N8 1.01(17) . . . . ?
N6 C34 C39 C38 -178.27(14) . . . . ?
N7 N6 C32 N5 -115.34(15) . . . . ?
N7 N6 C32 C33 11.20(19) . . . . ?
N7 N6 C34 C35 178.90(16) . . . . ?
N7 N6 C34 C39 -1.02(16) . . . . ?
N7 N8 C39 C34 -0.65(17) . . . . ?
N7 N8 C39 C38 178.53(16) . . . . ?
C20 C21 C22 C23 0.1(3) . . . . ?
C21 C20 C31 N5 178.23(17) . . . . ?
C21 C20 C31 C24 -0.3(3) . . . . ?
C21 C22 C23 C24 -1.0(3) . . . . ?
C22 C23 C24 C25 -177.84(18) . . . . ?
C22 C23 C24 C31 1.2(3) . . . . ?
C23 C24 C25 C26 0.2(3) . . . . ?
C23 C24 C25 C30 178.70(19) . . . . ?
C23 C24 C31 N5 -179.36(15) . . . . ?
C23 C24 C31 C20 -0.5(3) . . . . ?
C24 C25 C26 C27 177.00(17) . . . . ?
C24 C25 C30 N5 0.77(18) . . . . ?
C24 C25 C30 C29 -177.17(15) . . . . ?
C25 C24 C31 N5 -0.08(18) . . . . ?
C25 C24 C31 C20 178.75(16) . . . . ?
C25 C26 C27 C28 0.1(3) . . . . ?
C26 C25 C30 N5 179.51(14) . . . . ?
C26 C25 C30 C29 1.6(2) . . . . ?
C26 C27 C28 C29 1.1(3) . . . . ?
C27 C28 C29 C30 -0.9(2) . . . . ?
C28 C29 C30 N5 -177.92(16) . . . . ?
C28 C29 C30 C25 -0.4(2) . . . . ?
C30 N5 C31 C20 -178.17(17) . . . . ?
C30 N5 C31 C24 0.55(18) . . . . ?
C30 N5 C32 N6 72.76(19) . . . . ?
C30 N5 C32 C33 -53.1(2) . . . . ?
C30 C25 C26 C27 -1.4(2) . . . . ?
C31 N5 C30 C25 -0.82(18) . . . . ?
C31 N5 C30 C29 176.92(16) . . . . ?
C31 N5 C32 N6 -129.52(15) . . . . ?
C31 N5 C32 C33 104.60(17) . . . . ?
C31 C20 C21 C22 0.5(3) . . . . ?
C31 C24 C25 C26 -178.92(18) . . . . ?
C31 C24 C25 C30 -0.42(18) . . . . ?
C32 N5 C30 C25 159.69(15) . . . . ?
C32 N5 C30 C29 -22.6(3) . . . . ?
C32 N5 C31 C20 20.8(3) . . . . ?
C32 N5 C31 C24 -160.44(14) . . . . ?
C32 N6 N7 N8 -178.73(13) . . . . ?
C32 N6 C34 C35 -1.8(3) . . . . ?
C32 N6 C34 C39 178.33(14) . . . . ?
C34 N6 N7 N8 0.65(17) . . . . ?
C34 N6 C32 N5 65.39(19) . . . . ?
C34 N6 C32 C33 -168.07(14) . . . . ?
C34 C35 C36 C37 -0.9(2) . . . . ?
C35 C34 C39 N8 -178.91(14) . . . . ?
C35 C34 C39 C38 1.8(2) . . . . ?
C35 C36 C37 C38 1.8(3) . . . . ?
C36 C37 C38 C39 -0.8(2) . . . . ?
C37 C38 C39 N8 179.99(16) . . . . ?
C37 C38 C39 C34 -0.9(2) . . . . ?
C39 C34 C35 C36 -0.8(2) . . . . ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2338362'
loop_
_audit_author_name
_audit_author_address
'Yi Jin'
;Yunnan University
China
;
_audit_update_record             
;
2024-03-07 deposited with the CCDC.	2024-03-22 downloaded from the CCDC.
;
_audit_creation_date             2024-03-04
_audit_creation_method           
;
FinalCif V88 by Daniel Kratzert, Freiburg 2024,
https://github.com/dkratzert/FinalCif
;
_diffrn_source_power             0.07
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C20 H15 Cl N4'
_chemical_formula_moiety         'C20 H15 Cl N4'
_chemical_formula_weight         346.81
_exptl_crystal_colour_primary    colourless
_chemical_melting_point          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C33(H33), C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C40(H40), C8(H8), C22(H22), C31(H31), C10(H10), C9(H9), C11(H11),
 C23(H23), C25(H25), C5(H5), C28(H28), C2(H2), C24(H24), C4(H4), C3(H3),
 C37(H37), C38(H38), C18(H18), C30(H30), C29(H29), C17(H17)
2.c Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C14(H14A,H14B,H14C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.4084(4)
_cell_length_b                   21.4394(9)
_cell_length_c                   16.9249(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.0240(10)
_cell_angle_gamma                90
_cell_volume                     3395.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    298.15
_cell_measurement_reflns_used    6581
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      27.83
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6796
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1506 before and 0.0792 after correction.
The Ratio of minimum to maximum transmission is 0.9114.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.963
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      298.15
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.4
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            49671
_diffrn_reflns_av_unetI/netI     0.0833
_diffrn_reflns_av_R_equivalents  0.1146
_diffrn_reflns_theta_min         2.252
_diffrn_reflns_theta_max         28.370
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8475
_reflns_number_gt                4232
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0340P)²+3.5024P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         8475
_refine_ls_number_parameters     453
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1993
_refine_ls_R_factor_gt           0.0981
_refine_ls_wR_factor_ref         0.1840
_refine_ls_wR_factor_gt          0.1490
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.115
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

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'
Cl Cl 0.1484 0.1585 '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'

_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_
_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
Cl1 Cl 0.87243(14) 0.83026(6) 0.23675(8) 0.0877(4) Uani 1 1 d . . . . .
Cl2 Cl 1.35718(15) 0.49650(6) 0.58742(8) 0.0954(5) Uani 1 1 d . . . . .
N5 N 1.0279(3) 0.54891(13) 0.25970(17) 0.0450(7) Uani 1 1 d . . . . .
N6 N 1.0187(3) 0.61378(13) 0.37487(17) 0.0458(7) Uani 1 1 d . . . . .
N1 N 0.5018(3) 0.77029(13) 0.49122(19) 0.0506(8) Uani 1 1 d . . . . .
N2 N 0.5336(3) 0.69558(14) 0.3901(2) 0.0528(8) Uani 1 1 d . . . . .
N7 N 0.8986(3) 0.64754(15) 0.3830(2) 0.0623(9) Uani 1 1 d . . . . .
N3 N 0.4314(4) 0.65325(15) 0.3623(3) 0.0687(10) Uani 1 1 d . . . . .
N8 N 0.8744(4) 0.64679(17) 0.4575(2) 0.0678(10) Uani 1 1 d . . . . .
C32 C 1.1175(4) 0.49831(16) 0.2496(2) 0.0457(9) Uani 1 1 d . . . . .
N4 N 0.4229(4) 0.65311(17) 0.2851(3) 0.0749(11) Uani 1 1 d . . . . .
C35 C 1.0711(4) 0.58989(16) 0.4469(2) 0.0443(9) Uani 1 1 d . . . . .
C21 C 0.8904(4) 0.53468(16) 0.2248(2) 0.0452(9) Uani 1 1 d . . . . .
C1 C 0.3570(4) 0.78674(17) 0.4808(2) 0.0501(9) Uani 1 1 d . . . . .
C33 C 1.0758(4) 0.60719(15) 0.2977(2) 0.0448(9) Uani 1 1 d . . . . .
H33 H 1.179779 0.603912 0.309146 0.054 Uiso 1 1 calc R U . . .
C15 C 0.5914(4) 0.72250(16) 0.3286(2) 0.0475(9) Uani 1 1 d . . . . .
C12 C 0.5805(4) 0.82269(16) 0.5183(2) 0.0459(9) Uani 1 1 d . . . . .
C26 C 0.8937(4) 0.47494(16) 0.1906(2) 0.0459(9) Uani 1 1 d . . . . .
C27 C 1.0368(4) 0.45159(16) 0.2077(2) 0.0476(9) Uani 1 1 d . . . . .
C7 C 0.4856(4) 0.87231(16) 0.5261(2) 0.0457(9) Uani 1 1 d . . . . .
C6 C 0.3445(4) 0.84960(17) 0.5019(2) 0.0468(9) Uani 1 1 d . . . . .
C20 C 0.7003(4) 0.76622(16) 0.3235(2) 0.0501(9) Uani 1 1 d . . . . .
H20 H 0.747996 0.784841 0.368352 0.060 Uiso 1 1 calc R U . . .
C36 C 0.9793(4) 0.61169(18) 0.4993(2) 0.0554(10) Uani 1 1 d . . . . .
C40 C 1.1901(4) 0.55353(16) 0.4716(2) 0.0519(10) Uani 1 1 d . . . . .
H40 H 1.251416 0.538628 0.436266 0.062 Uiso 1 1 calc R U . . .
C13 C 0.5627(4) 0.71006(16) 0.4751(2) 0.0522(10) Uani 1 1 d . . . . .
H13 H 0.666607 0.714181 0.486376 0.063 Uiso 1 1 calc R U . . .
C8 C 0.5389(5) 0.92997(17) 0.5519(2) 0.0549(10) Uani 1 1 d . . . . .
H8 H 0.477352 0.963336 0.556936 0.066 Uiso 1 1 calc R U . . .
C16 C 0.5198(4) 0.69551(19) 0.2611(3) 0.0591(11) Uani 1 1 d . . . . .
C34 C 1.0478(4) 0.66406(17) 0.2459(2) 0.0575(10) Uani 1 1 d . . . . .
H34A H 1.094798 0.659378 0.198563 0.086 Uiso 1 1 calc R U . . .
H34B H 1.084042 0.700418 0.274364 0.086 Uiso 1 1 calc R U . . .
H34C H 0.946816 0.668555 0.231785 0.086 Uiso 1 1 calc R U . . .
C22 C 0.7638(4) 0.56809(18) 0.2239(2) 0.0545(10) Uani 1 1 d . . . . .
H22 H 0.761238 0.606920 0.248174 0.065 Uiso 1 1 calc R U . . .
C31 C 1.2619(4) 0.49125(18) 0.2732(2) 0.0552(10) Uani 1 1 d . . . . .
H31 H 1.315400 0.523060 0.299218 0.066 Uiso 1 1 calc R U . . .
C10 C 0.7758(4) 0.8876(2) 0.5626(2) 0.0617(11) Uani 1 1 d . . . . .
H10 H 0.873424 0.893508 0.575493 0.074 Uiso 1 1 calc R U . . .
C9 C 0.6839(5) 0.93717(19) 0.5698(2) 0.0624(11) Uani 1 1 d . . . . .
H9 H 0.720526 0.975706 0.586986 0.075 Uiso 1 1 calc R U . . .
C11 C 0.7271(4) 0.82951(19) 0.5369(2) 0.0568(10) Uani 1 1 d . . . . .
H11 H 0.789606 0.796441 0.532142 0.068 Uiso 1 1 calc R U . . .
C19 C 0.7323(4) 0.77990(18) 0.2482(3) 0.0583(10) Uani 1 1 d . . . . .
C23 C 0.6416(4) 0.5415(2) 0.1855(2) 0.0634(11) Uani 1 1 d . . . . .
H23 H 0.555231 0.562726 0.184594 0.076 Uiso 1 1 calc R U . . .
C25 C 0.7685(5) 0.45038(19) 0.1508(2) 0.0602(11) Uani 1 1 d . . . . .
H25 H 0.769265 0.411607 0.126242 0.072 Uiso 1 1 calc R U . . .
C39 C 1.2108(4) 0.54122(18) 0.5510(2) 0.0593(11) Uani 1 1 d . . . . .
C5 C 0.2100(4) 0.8777(2) 0.4951(2) 0.0613(11) Uani 1 1 d . . . . .
H5 H 0.199306 0.918987 0.510101 0.074 Uiso 1 1 calc R U . . .
C28 C 1.1027(5) 0.39517(18) 0.1923(2) 0.0633(11) Uani 1 1 d . . . . .
H28 H 1.050752 0.363273 0.165525 0.076 Uiso 1 1 calc R U . . .
C2 C 0.2386(4) 0.75169(19) 0.4519(3) 0.0645(12) Uani 1 1 d . . . . .
H2 H 0.247529 0.710095 0.437626 0.077 Uiso 1 1 calc R U . . .
C24 C 0.6444(5) 0.4842(2) 0.1486(3) 0.0684(12) Uani 1 1 d . . . . .
H24 H 0.560941 0.468318 0.121688 0.082 Uiso 1 1 calc R U . . .
C4 C 0.0934(4) 0.8427(2) 0.4656(3) 0.0710(13) Uani 1 1 d . . . . .
H4 H 0.003439 0.861124 0.459404 0.085 Uiso 1 1 calc R U . . .
C3 C 0.1074(4) 0.7809(2) 0.4452(3) 0.0708(13) Uani 1 1 d . . . . .
H3 H 0.026339 0.758443 0.426436 0.085 Uiso 1 1 calc R U . . .
C37 C 1.0031(5) 0.5980(2) 0.5802(3) 0.0725(13) Uani 1 1 d . . . . .
H37 H 0.941453 0.612290 0.615802 0.087 Uiso 1 1 calc R U . . .
C38 C 1.1201(5) 0.5630(2) 0.6051(3) 0.0714(13) Uani 1 1 d . . . . .
H38 H 1.139706 0.553396 0.658778 0.086 Uiso 1 1 calc R U . . .
C18 C 0.6616(5) 0.7539(2) 0.1794(3) 0.0724(13) Uani 1 1 d . . . . .
H18 H 0.687265 0.765061 0.129718 0.087 Uiso 1 1 calc R U . . .
C30 C 1.3229(5) 0.4350(2) 0.2566(3) 0.0701(12) Uani 1 1 d . . . . .
H30 H 1.419518 0.428611 0.272339 0.084 Uiso 1 1 calc R U . . .
C29 C 1.2442(5) 0.3875(2) 0.2169(3) 0.0747(13) Uani 1 1 d . . . . .
H29 H 1.288672 0.349919 0.207131 0.090 Uiso 1 1 calc R U . . .
C17 C 0.5546(5) 0.7119(2) 0.1858(3) 0.0777(14) Uani 1 1 d . . . . .
H17 H 0.505492 0.694496 0.140519 0.093 Uiso 1 1 calc R U . . .
C14 C 0.5173(5) 0.65810(19) 0.5277(3) 0.0782(14) Uani 1 1 d . . . . .
H14A H 0.547492 0.667749 0.582231 0.117 Uiso 1 1 calc R U . . .
H14B H 0.560540 0.619655 0.513596 0.117 Uiso 1 1 calc R U . . .
H14C H 0.415193 0.653964 0.520426 0.117 Uiso 1 1 calc R U . . .


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
Cl1 C19 1.731(4) . ?
Cl2 C39 1.737(4) . ?
N5 C32 1.395(4) . ?
N5 C21 1.398(4) . ?
N5 C33 1.455(4) . ?
N6 N7 1.361(4) . ?
N6 C35 1.365(4) . ?
N6 C33 1.470(4) . ?
N1 C1 1.401(4) . ?
N1 C12 1.396(4) . ?
N1 C13 1.450(4) . ?
N2 N3 1.369(4) . ?
N2 C15 1.354(5) . ?
N2 C13 1.469(5) . ?
N7 N8 1.304(4) . ?
N3 N4 1.301(5) . ?
N8 C36 1.376(5) . ?
C32 C27 1.403(5) . ?
C32 C31 1.384(5) . ?
N4 C16 1.379(5) . ?
C35 C36 1.383(5) . ?
C35 C40 1.392(5) . ?
C21 C26 1.407(5) . ?
C21 C22 1.389(5) . ?
C1 C6 1.402(5) . ?
C1 C2 1.389(5) . ?
C33 H33 0.9800 . ?
C33 C34 1.509(5) . ?
C15 C20 1.398(5) . ?
C15 C16 1.390(5) . ?
C12 C7 1.404(5) . ?
C12 C11 1.390(5) . ?
C26 C27 1.437(5) . ?
C26 C25 1.397(5) . ?
C27 C28 1.396(5) . ?
C7 C6 1.433(5) . ?
C7 C8 1.387(5) . ?
C6 C5 1.395(5) . ?
C20 H20 0.9300 . ?
C20 C19 1.372(5) . ?
C36 C37 1.395(6) . ?
C40 H40 0.9300 . ?
C40 C39 1.363(5) . ?
C13 H13 0.9800 . ?
C13 C14 1.514(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.375(5) . ?
C16 C17 1.394(6) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C22 H22 0.9300 . ?
C22 C23 1.383(5) . ?
C31 H31 0.9300 . ?
C31 C30 1.378(5) . ?
C10 H10 0.9300 . ?
C10 C9 1.384(6) . ?
C10 C11 1.381(5) . ?
C9 H9 0.9300 . ?
C11 H11 0.9300 . ?
C19 C18 1.395(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.379(6) . ?
C25 H25 0.9300 . ?
C25 C24 1.372(6) . ?
C39 C38 1.397(6) . ?
C5 H5 0.9300 . ?
C5 C4 1.379(6) . ?
C28 H28 0.9300 . ?
C28 C29 1.363(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(5) . ?
C24 H24 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.378(6) . ?
C3 H3 0.9300 . ?
C37 H37 0.9300 . ?
C37 C38 1.363(6) . ?
C38 H38 0.9300 . ?
C18 H18 0.9300 . ?
C18 C17 1.363(6) . ?
C30 H30 0.9300 . ?
C30 C29 1.390(6) . ?
C29 H29 0.9300 . ?
C17 H17 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
C32 N5 C21 108.8(3) . . ?
C32 N5 C33 124.0(3) . . ?
C21 N5 C33 127.2(3) . . ?
N7 N6 C35 109.6(3) . . ?
N7 N6 C33 121.7(3) . . ?
C35 N6 C33 128.7(3) . . ?
C1 N1 C13 126.8(3) . . ?
C12 N1 C1 108.3(3) . . ?
C12 N1 C13 124.9(3) . . ?
N3 N2 C13 121.9(3) . . ?
C15 N2 N3 110.0(3) . . ?
C15 N2 C13 127.9(3) . . ?
N8 N7 N6 108.8(3) . . ?
N4 N3 N2 108.3(3) . . ?
N7 N8 C36 108.4(3) . . ?
N5 C32 C27 108.4(3) . . ?
C31 C32 N5 129.6(3) . . ?
C31 C32 C27 122.0(3) . . ?
N3 N4 C16 108.8(3) . . ?
N6 C35 C36 104.8(3) . . ?
N6 C35 C40 133.0(3) . . ?
C36 C35 C40 122.2(4) . . ?
N5 C21 C26 108.2(3) . . ?
C22 C21 N5 130.3(3) . . ?
C22 C21 C26 121.4(3) . . ?
N1 C1 C6 108.5(3) . . ?
C2 C1 N1 129.9(3) . . ?
C2 C1 C6 121.6(3) . . ?
N5 C33 N6 110.5(3) . . ?
N5 C33 H33 106.4 . . ?
N5 C33 C34 114.2(3) . . ?
N6 C33 H33 106.4 . . ?
N6 C33 C34 112.4(3) . . ?
C34 C33 H33 106.4 . . ?
N2 C15 C20 133.5(4) . . ?
N2 C15 C16 104.8(3) . . ?
C16 C15 C20 121.6(4) . . ?
N1 C12 C7 108.7(3) . . ?
C11 C12 N1 129.7(3) . . ?
C11 C12 C7 121.7(3) . . ?
C21 C26 C27 107.2(3) . . ?
C25 C26 C21 119.2(4) . . ?
C25 C26 C27 133.7(4) . . ?
C32 C27 C26 107.4(3) . . ?
C28 C27 C32 119.1(4) . . ?
C28 C27 C26 133.6(4) . . ?
C12 C7 C6 107.2(3) . . ?
C8 C7 C12 119.5(4) . . ?
C8 C7 C6 133.3(4) . . ?
C1 C6 C7 107.4(3) . . ?
C5 C6 C1 119.6(4) . . ?
C5 C6 C7 133.0(4) . . ?
C15 C20 H20 122.2 . . ?
C19 C20 C15 115.7(4) . . ?
C19 C20 H20 122.2 . . ?
N8 C36 C35 108.4(4) . . ?
N8 C36 C37 130.7(4) . . ?
C35 C36 C37 120.8(4) . . ?
C35 C40 H40 122.2 . . ?
C39 C40 C35 115.6(4) . . ?
C39 C40 H40 122.2 . . ?
N1 C13 N2 109.6(3) . . ?
N1 C13 H13 106.8 . . ?
N1 C13 C14 113.8(3) . . ?
N2 C13 H13 106.8 . . ?
N2 C13 C14 112.6(3) . . ?
C14 C13 H13 106.8 . . ?
C7 C8 H8 120.4 . . ?
C9 C8 C7 119.2(4) . . ?
C9 C8 H8 120.4 . . ?
N4 C16 C15 108.1(4) . . ?
N4 C16 C17 131.5(4) . . ?
C15 C16 C17 120.4(4) . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C21 C22 H22 121.2 . . ?
C23 C22 C21 117.5(4) . . ?
C23 C22 H22 121.2 . . ?
C32 C31 H31 121.5 . . ?
C30 C31 C32 117.0(4) . . ?
C30 C31 H31 121.5 . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C11 C10 C9 122.0(4) . . ?
C8 C9 C10 120.6(4) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C12 C11 H11 121.5 . . ?
C10 C11 C12 117.1(4) . . ?
C10 C11 H11 121.5 . . ?
C20 C19 Cl1 118.8(3) . . ?
C20 C19 C18 123.9(4) . . ?
C18 C19 Cl1 117.2(4) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 C22 121.7(4) . . ?
C24 C23 H23 119.2 . . ?
C26 C25 H25 120.4 . . ?
C24 C25 C26 119.1(4) . . ?
C24 C25 H25 120.4 . . ?
C40 C39 Cl2 118.9(3) . . ?
C40 C39 C38 123.3(4) . . ?
C38 C39 Cl2 117.9(3) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 C6 118.4(4) . . ?
C4 C5 H5 120.8 . . ?
C27 C28 H28 120.4 . . ?
C29 C28 C27 119.1(4) . . ?
C29 C28 H28 120.4 . . ?
C1 C2 H2 121.3 . . ?
C3 C2 C1 117.4(4) . . ?
C3 C2 H2 121.3 . . ?
C23 C24 H24 119.5 . . ?
C25 C24 C23 121.0(4) . . ?
C25 C24 H24 119.5 . . ?
C5 C4 H4 119.3 . . ?
C3 C4 C5 121.3(4) . . ?
C3 C4 H4 119.3 . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.7(4) . . ?
C4 C3 H3 119.2 . . ?
C36 C37 H37 121.3 . . ?
C38 C37 C36 117.4(4) . . ?
C38 C37 H37 121.3 . . ?
C39 C38 H38 119.6 . . ?
C37 C38 C39 120.7(4) . . ?
C37 C38 H38 119.6 . . ?
C19 C18 H18 120.4 . . ?
C17 C18 C19 119.3(4) . . ?
C17 C18 H18 120.4 . . ?
C31 C30 H30 119.1 . . ?
C31 C30 C29 121.9(4) . . ?
C29 C30 H30 119.1 . . ?
C28 C29 C30 120.9(4) . . ?
C28 C29 H29 119.6 . . ?
C30 C29 H29 119.6 . . ?
C16 C17 H17 120.5 . . ?
C18 C17 C16 119.0(4) . . ?
C18 C17 H17 120.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C19 C18 C17 177.2(4) . . . . ?
Cl2 C39 C38 C37 -179.7(3) . . . . ?
N5 C32 C27 C26 0.9(4) . . . . ?
N5 C32 C27 C28 -178.1(3) . . . . ?
N5 C32 C31 C30 178.6(4) . . . . ?
N5 C21 C26 C27 1.8(4) . . . . ?
N5 C21 C26 C25 -179.2(3) . . . . ?
N5 C21 C22 C23 -178.6(4) . . . . ?
N6 N7 N8 C36 -0.4(4) . . . . ?
N6 C35 C36 N8 0.9(4) . . . . ?
N6 C35 C36 C37 -177.8(4) . . . . ?
N6 C35 C40 C39 176.9(4) . . . . ?
N1 C1 C6 C7 -0.2(4) . . . . ?
N1 C1 C6 C5 178.7(3) . . . . ?
N1 C1 C2 C3 -177.5(4) . . . . ?
N1 C12 C7 C6 -0.8(4) . . . . ?
N1 C12 C7 C8 -179.6(3) . . . . ?
N1 C12 C11 C10 180.0(4) . . . . ?
N2 N3 N4 C16 0.1(5) . . . . ?
N2 C15 C20 C19 177.2(4) . . . . ?
N2 C15 C16 N4 -0.5(4) . . . . ?
N2 C15 C16 C17 -178.9(4) . . . . ?
N7 N6 C35 C36 -1.2(4) . . . . ?
N7 N6 C35 C40 -178.9(4) . . . . ?
N7 N6 C33 N5 -96.9(4) . . . . ?
N7 N6 C33 C34 32.0(4) . . . . ?
N7 N8 C36 C35 -0.3(4) . . . . ?
N7 N8 C36 C37 178.3(4) . . . . ?
N3 N2 C15 C20 -177.6(4) . . . . ?
N3 N2 C15 C16 0.5(4) . . . . ?
N3 N2 C13 N1 -104.5(4) . . . . ?
N3 N2 C13 C14 23.2(5) . . . . ?
N3 N4 C16 C15 0.3(5) . . . . ?
N3 N4 C16 C17 178.5(4) . . . . ?
N8 C36 C37 C38 -178.0(4) . . . . ?
C32 N5 C21 C26 -1.3(4) . . . . ?
C32 N5 C21 C22 175.3(4) . . . . ?
C32 N5 C33 N6 -110.3(4) . . . . ?
C32 N5 C33 C34 121.8(4) . . . . ?
C32 C27 C28 C29 -1.3(6) . . . . ?
C32 C31 C30 C29 0.8(6) . . . . ?
N4 C16 C17 C18 -176.7(4) . . . . ?
C35 N6 N7 N8 1.1(4) . . . . ?
C35 N6 C33 N5 83.6(4) . . . . ?
C35 N6 C33 C34 -147.5(3) . . . . ?
C35 C36 C37 C38 0.4(6) . . . . ?
C35 C40 C39 Cl2 -179.7(3) . . . . ?
C35 C40 C39 C38 0.1(6) . . . . ?
C21 N5 C32 C27 0.2(4) . . . . ?
C21 N5 C32 C31 179.2(4) . . . . ?
C21 N5 C33 N6 72.6(4) . . . . ?
C21 N5 C33 C34 -55.3(5) . . . . ?
C21 C26 C27 C32 -1.7(4) . . . . ?
C21 C26 C27 C28 177.1(4) . . . . ?
C21 C26 C25 C24 -2.3(6) . . . . ?
C21 C22 C23 C24 -0.7(6) . . . . ?
C1 N1 C12 C7 0.7(4) . . . . ?
C1 N1 C12 C11 -179.9(4) . . . . ?
C1 N1 C13 N2 62.4(5) . . . . ?
C1 N1 C13 C14 -64.7(5) . . . . ?
C1 C6 C5 C4 -1.7(6) . . . . ?
C1 C2 C3 C4 0.5(7) . . . . ?
C33 N5 C32 C27 -177.3(3) . . . . ?
C33 N5 C32 C31 1.7(6) . . . . ?
C33 N5 C21 C26 176.1(3) . . . . ?
C33 N5 C21 C22 -7.2(6) . . . . ?
C33 N6 N7 N8 -178.5(3) . . . . ?
C33 N6 C35 C36 178.3(3) . . . . ?
C33 N6 C35 C40 0.6(6) . . . . ?
C15 N2 N3 N4 -0.4(4) . . . . ?
C15 N2 C13 N1 70.9(4) . . . . ?
C15 N2 C13 C14 -161.3(3) . . . . ?
C15 C20 C19 Cl1 -176.4(3) . . . . ?
C15 C20 C19 C18 1.2(6) . . . . ?
C15 C16 C17 C18 1.3(6) . . . . ?
C12 N1 C1 C6 -0.3(4) . . . . ?
C12 N1 C1 C2 176.9(4) . . . . ?
C12 N1 C13 N2 -115.9(4) . . . . ?
C12 N1 C13 C14 117.0(4) . . . . ?
C12 C7 C6 C1 0.6(4) . . . . ?
C12 C7 C6 C5 -178.0(4) . . . . ?
C12 C7 C8 C9 -0.5(5) . . . . ?
C26 C21 C22 C23 -2.4(6) . . . . ?
C26 C27 C28 C29 180.0(4) . . . . ?
C26 C25 C24 C23 -0.7(6) . . . . ?
C27 C32 C31 C30 -2.5(6) . . . . ?
C27 C26 C25 C24 176.4(4) . . . . ?
C27 C28 C29 C30 -0.3(7) . . . . ?
C7 C12 C11 C10 -0.6(6) . . . . ?
C7 C6 C5 C4 176.8(4) . . . . ?
C7 C8 C9 C10 -0.2(6) . . . . ?
C6 C1 C2 C3 -0.5(6) . . . . ?
C6 C7 C8 C9 -178.9(4) . . . . ?
C6 C5 C4 C3 1.8(6) . . . . ?
C20 C15 C16 N4 177.9(3) . . . . ?
C20 C15 C16 C17 -0.5(6) . . . . ?
C20 C19 C18 C17 -0.5(7) . . . . ?
C36 C35 C40 C39 -0.5(5) . . . . ?
C36 C37 C38 C39 -0.7(6) . . . . ?
C40 C35 C36 N8 179.0(3) . . . . ?
C40 C35 C36 C37 0.2(6) . . . . ?
C40 C39 C38 C37 0.5(7) . . . . ?
C13 N1 C1 C6 -178.9(3) . . . . ?
C13 N1 C1 C2 -1.6(7) . . . . ?
C13 N1 C12 C7 179.3(3) . . . . ?
C13 N1 C12 C11 -1.3(6) . . . . ?
C13 N2 N3 N4 175.8(3) . . . . ?
C13 N2 C15 C20 6.5(6) . . . . ?
C13 N2 C15 C16 -175.4(3) . . . . ?
C8 C7 C6 C1 179.2(4) . . . . ?
C8 C7 C6 C5 0.6(7) . . . . ?
C16 C15 C20 C19 -0.7(5) . . . . ?
C22 C21 C26 C27 -175.1(3) . . . . ?
C22 C21 C26 C25 3.9(5) . . . . ?
C22 C23 C24 C25 2.3(7) . . . . ?
C31 C32 C27 C26 -178.2(3) . . . . ?
C31 C32 C27 C28 2.8(5) . . . . ?
C31 C30 C29 C28 0.6(7) . . . . ?
C9 C10 C11 C12 0.0(6) . . . . ?
C11 C12 C7 C6 179.7(3) . . . . ?
C11 C12 C7 C8 0.9(5) . . . . ?
C11 C10 C9 C8 0.5(6) . . . . ?
C19 C18 C17 C16 -0.8(7) . . . . ?
C25 C26 C27 C32 179.5(4) . . . . ?
C25 C26 C27 C28 -1.7(7) . . . . ?
C5 C4 C3 C2 -1.2(7) . . . . ?
C2 C1 C6 C7 -177.7(4) . . . . ?
C2 C1 C6 C5 1.1(6) . . . . ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2338361'
loop_
_audit_author_name
_audit_author_address
'Yi Jin'
;Yunnan University
China
;
_audit_update_record             
;
2024-03-07 deposited with the CCDC.	2024-03-22 downloaded from the CCDC.
;
_audit_creation_date             2024-02-29
_diffrn_source_power             0.07
_audit_creation_method           
;
FinalCif V88 by Daniel Kratzert, Freiburg 2024,
https://github.com/dkratzert/FinalCif
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C20 H15 Cl N4'
_chemical_formula_moiety         'C20 H15 Cl N4'
_exptl_crystal_colour_primary    colourless
_chemical_formula_weight         346.81
_chemical_melting_point          ?
_chemical_absolute_configuration ad
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13), C17(H17),
 C18(H18), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.9868(4)
_cell_length_b                   12.6657(5)
_cell_length_c                   13.3981(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1694.72(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    298.15
_cell_measurement_reflns_used    4651
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      27.70
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7032
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1142 before and 0.0594 after correction.
The Ratio of minimum to maximum transmission is 0.9430.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.955
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      298.15
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.4
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            14297
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_theta_min         2.213
_diffrn_reflns_theta_max         28.295
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4189
_reflns_number_gt                2857
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_max     0.983
_reflns_Friedel_fraction_full    0.995
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0359P)²+0.1793P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4189
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0945
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1071
_refine_ls_wR_factor_gt          0.0910
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_abs_structure_details 
;
 Flack x determined using 890 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

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'
Cl Cl 0.1484 0.1585 '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'

_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_
_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
Cl1 Cl 0.97328(11) 0.25706(7) 0.46596(9) 0.0850(4) Uani 1 1 d . . . . .
N1 N 0.4876(2) 0.67108(19) 0.48321(17) 0.0463(6) Uani 1 1 d . . . . .
N2 N 0.6094(3) 0.57844(19) 0.60855(18) 0.0443(6) Uani 1 1 d . . . . .
N3 N 0.5798(3) 0.5349(2) 0.69860(19) 0.0572(7) Uani 1 1 d . . . . .
N4 N 0.6455(3) 0.4466(2) 0.7082(2) 0.0608(8) Uani 1 1 d . . . . .
C1 C 0.8645(3) 0.3563(3) 0.5057(3) 0.0551(9) Uani 1 1 d . . . . .
C2 C 0.8067(3) 0.3490(3) 0.5974(3) 0.0560(9) Uani 1 1 d . . . . .
H2 H 0.823754 0.293020 0.640491 0.067 Uiso 1 1 calc R U . . .
C3 C 0.7199(3) 0.4316(2) 0.6227(2) 0.0470(7) Uani 1 1 d . . . . .
C4 C 0.6967(3) 0.5154(2) 0.5582(2) 0.0413(7) Uani 1 1 d . . . . .
C5 C 0.7575(3) 0.5212(3) 0.4649(2) 0.0506(8) Uani 1 1 d . . . . .
H5 H 0.742116 0.577324 0.421593 0.061 Uiso 1 1 calc R U . . .
C6 C 0.8407(4) 0.4403(3) 0.4407(3) 0.0595(9) Uani 1 1 d . . . . .
H6 H 0.883030 0.440897 0.378893 0.071 Uiso 1 1 calc R U . . .
C7 C 0.5535(3) 0.6808(2) 0.5794(2) 0.0480(8) Uani 1 1 d . . . . .
H7 H 0.628553 0.729956 0.571239 0.058 Uiso 1 1 calc R U . . .
C8 C 0.4624(4) 0.7258(3) 0.6586(3) 0.0703(11) Uani 1 1 d . . . . .
H8A H 0.383870 0.682448 0.664305 0.105 Uiso 1 1 calc R U . . .
H8B H 0.436702 0.796224 0.640402 0.105 Uiso 1 1 calc R U . . .
H8C H 0.508575 0.727195 0.721410 0.105 Uiso 1 1 calc R U . . .
C9 C 0.3899(3) 0.5973(2) 0.4563(2) 0.0453(7) Uani 1 1 d . . . . .
C10 C 0.3485(3) 0.5062(2) 0.5048(3) 0.0570(9) Uani 1 1 d . . . . .
H10 H 0.385955 0.486044 0.565461 0.068 Uiso 1 1 calc R U . . .
C11 C 0.2498(3) 0.4466(3) 0.4599(4) 0.0686(10) Uani 1 1 d . . . . .
H11 H 0.220603 0.385199 0.491081 0.082 Uiso 1 1 calc R U . . .
C12 C 0.1934(4) 0.4754(3) 0.3704(3) 0.0749(12) Uani 1 1 d . . . . .
H12 H 0.127448 0.433155 0.342029 0.090 Uiso 1 1 calc R U . . .
C13 C 0.2336(4) 0.5666(3) 0.3220(3) 0.0664(11) Uani 1 1 d . . . . .
H13 H 0.194663 0.586207 0.261710 0.080 Uiso 1 1 calc R U . . .
C14 C 0.3334(3) 0.6283(3) 0.3650(2) 0.0507(8) Uani 1 1 d . . . . .
C15 C 0.3969(3) 0.7258(3) 0.3363(2) 0.0526(8) Uani 1 1 d . . . . .
C16 C 0.4894(3) 0.7509(2) 0.4118(2) 0.0482(7) Uani 1 1 d . . . . .
C17 C 0.5627(4) 0.8435(3) 0.4102(3) 0.0634(10) Uani 1 1 d . . . . .
H17 H 0.621237 0.860397 0.461766 0.076 Uiso 1 1 calc R U . . .
C18 C 0.5459(5) 0.9099(3) 0.3295(3) 0.0814(12) Uani 1 1 d . . . . .
H18 H 0.594786 0.972316 0.326268 0.098 Uiso 1 1 calc R U . . .
C19 C 0.4577(5) 0.8853(4) 0.2535(3) 0.0875(14) Uani 1 1 d . . . . .
H19 H 0.448658 0.931485 0.199931 0.105 Uiso 1 1 calc R U . . .
C20 C 0.3833(4) 0.7942(4) 0.2554(3) 0.0752(12) Uani 1 1 d . . . . .
H20 H 0.324704 0.778364 0.203528 0.090 Uiso 1 1 calc R U . . .


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
Cl1 C1 1.744(3) . ?
N1 C7 1.453(4) . ?
N1 C9 1.398(4) . ?
N1 C16 1.393(4) . ?
N2 N3 1.359(3) . ?
N2 C4 1.362(4) . ?
N2 C7 1.465(4) . ?
N3 N4 1.304(4) . ?
N4 C3 1.379(4) . ?
C1 C2 1.361(5) . ?
C1 C6 1.396(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.400(4) . ?
C3 C4 1.388(4) . ?
C4 C5 1.392(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.359(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9800 . ?
C7 C8 1.509(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.387(4) . ?
C9 C14 1.403(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.380(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.374(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.384(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.392(5) . ?
C14 C15 1.441(5) . ?
C15 C16 1.406(4) . ?
C15 C20 1.394(5) . ?
C16 C17 1.382(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.380(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.382(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.374(6) . ?
C20 H20 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
C9 N1 C7 127.0(2) . . ?
C16 N1 C7 122.9(2) . . ?
C16 N1 C9 108.5(2) . . ?
N3 N2 C4 109.9(2) . . ?
N3 N2 C7 120.8(2) . . ?
C4 N2 C7 129.2(3) . . ?
N4 N3 N2 109.1(2) . . ?
N3 N4 C3 107.9(3) . . ?
C2 C1 Cl1 119.4(3) . . ?
C2 C1 C6 122.8(3) . . ?
C6 C1 Cl1 117.7(3) . . ?
C1 C2 H2 122.2 . . ?
C1 C2 C3 115.5(3) . . ?
C3 C2 H2 122.2 . . ?
N4 C3 C2 129.6(3) . . ?
N4 C3 C4 108.8(3) . . ?
C4 C3 C2 121.6(3) . . ?
N2 C4 C3 104.3(2) . . ?
N2 C4 C5 133.9(3) . . ?
C3 C4 C5 121.8(3) . . ?
C4 C5 H5 121.9 . . ?
C6 C5 C4 116.1(3) . . ?
C6 C5 H5 121.9 . . ?
C1 C6 H6 119.0 . . ?
C5 C6 C1 122.1(3) . . ?
C5 C6 H6 119.0 . . ?
N1 C7 N2 109.5(2) . . ?
N1 C7 H7 107.5 . . ?
N1 C7 C8 112.5(3) . . ?
N2 C7 H7 107.5 . . ?
N2 C7 C8 112.1(3) . . ?
C8 C7 H7 107.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C14 108.5(3) . . ?
C10 C9 N1 130.0(3) . . ?
C10 C9 C14 121.4(3) . . ?
C9 C10 H10 121.2 . . ?
C11 C10 C9 117.6(4) . . ?
C11 C10 H10 121.2 . . ?
C10 C11 H11 119.1 . . ?
C12 C11 C10 121.9(4) . . ?
C12 C11 H11 119.1 . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.8(4) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 120.6 . . ?
C12 C13 C14 118.8(4) . . ?
C14 C13 H13 120.6 . . ?
C9 C14 C15 107.2(3) . . ?
C13 C14 C9 119.5(3) . . ?
C13 C14 C15 133.3(3) . . ?
C16 C15 C14 106.9(3) . . ?
C20 C15 C14 134.3(3) . . ?
C20 C15 C16 118.8(3) . . ?
N1 C16 C15 108.8(3) . . ?
C17 C16 N1 129.3(3) . . ?
C17 C16 C15 122.0(3) . . ?
C16 C17 H17 121.2 . . ?
C18 C17 C16 117.7(4) . . ?
C18 C17 H17 121.2 . . ?
C17 C18 H18 119.4 . . ?
C17 C18 C19 121.2(4) . . ?
C19 C18 H18 119.4 . . ?
C18 C19 H19 119.3 . . ?
C20 C19 C18 121.4(4) . . ?
C20 C19 H19 119.3 . . ?
C15 C20 H20 120.5 . . ?
C19 C20 C15 118.9(4) . . ?
C19 C20 H20 120.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C1 C2 C3 -179.4(2) . . . . ?
Cl1 C1 C6 C5 180.0(3) . . . . ?
N1 C9 C10 C11 -179.1(3) . . . . ?
N1 C9 C14 C13 179.5(3) . . . . ?
N1 C9 C14 C15 -1.3(3) . . . . ?
N1 C16 C17 C18 179.9(3) . . . . ?
N2 N3 N4 C3 0.0(4) . . . . ?
N2 C4 C5 C6 -179.8(3) . . . . ?
N3 N2 C4 C3 -0.5(3) . . . . ?
N3 N2 C4 C5 179.3(3) . . . . ?
N3 N2 C7 N1 -126.7(3) . . . . ?
N3 N2 C7 C8 -1.2(4) . . . . ?
N3 N4 C3 C2 179.7(3) . . . . ?
N3 N4 C3 C4 -0.4(4) . . . . ?
N4 C3 C4 N2 0.5(3) . . . . ?
N4 C3 C4 C5 -179.3(3) . . . . ?
C1 C2 C3 N4 179.1(3) . . . . ?
C1 C2 C3 C4 -0.8(5) . . . . ?
C2 C1 C6 C5 0.1(5) . . . . ?
C2 C3 C4 N2 -179.5(3) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C4 N2 N3 N4 0.3(3) . . . . ?
C4 N2 C7 N1 55.9(4) . . . . ?
C4 N2 C7 C8 -178.6(3) . . . . ?
C4 C5 C6 C1 -0.3(5) . . . . ?
C6 C1 C2 C3 0.5(5) . . . . ?
C7 N1 C9 C10 -12.6(5) . . . . ?
C7 N1 C9 C14 168.0(3) . . . . ?
C7 N1 C16 C15 -168.9(3) . . . . ?
C7 N1 C16 C17 9.2(5) . . . . ?
C7 N2 N3 N4 -177.5(3) . . . . ?
C7 N2 C4 C3 177.1(3) . . . . ?
C7 N2 C4 C5 -3.1(5) . . . . ?
C9 N1 C7 N2 52.5(4) . . . . ?
C9 N1 C7 C8 -72.8(4) . . . . ?
C9 N1 C16 C15 -2.8(3) . . . . ?
C9 N1 C16 C17 175.3(3) . . . . ?
C9 C10 C11 C12 -0.1(5) . . . . ?
C9 C14 C15 C16 -0.4(3) . . . . ?
C9 C14 C15 C20 -179.4(4) . . . . ?
C10 C9 C14 C13 0.1(5) . . . . ?
C10 C9 C14 C15 179.2(3) . . . . ?
C10 C11 C12 C13 -0.4(6) . . . . ?
C11 C12 C13 C14 0.6(5) . . . . ?
C12 C13 C14 C9 -0.5(5) . . . . ?
C12 C13 C14 C15 -179.4(3) . . . . ?
C13 C14 C15 C16 178.7(3) . . . . ?
C13 C14 C15 C20 -0.4(6) . . . . ?
C14 C9 C10 C11 0.2(5) . . . . ?
C14 C15 C16 N1 1.9(3) . . . . ?
C14 C15 C16 C17 -176.4(3) . . . . ?
C14 C15 C20 C19 177.1(4) . . . . ?
C15 C16 C17 C18 -2.3(5) . . . . ?
C16 N1 C7 N2 -144.0(3) . . . . ?
C16 N1 C7 C8 90.7(3) . . . . ?
C16 N1 C9 C10 -178.1(3) . . . . ?
C16 N1 C9 C14 2.5(3) . . . . ?
C16 C15 C20 C19 -1.9(5) . . . . ?
C16 C17 C18 C19 0.7(6) . . . . ?
C17 C18 C19 C20 0.2(7) . . . . ?
C18 C19 C20 C15 0.4(6) . . . . ?
C20 C15 C16 N1 -178.9(3) . . . . ?
C20 C15 C16 C17 2.9(5) . . . . ?

