# Supplementary Information (SI) for ChemComm.
# 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. 
# 
#######################################################################

data_DOIM_TCNQ
_database_code_depnum_ccdc_archive 'CCDC 2457381'
loop_
_audit_author_name
_audit_author_address
'Ruifeng Shu'
;The University of Osaka
Japan
;
_audit_update_record             
;
2025-06-07 deposited with the CCDC.	2025-09-24 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C31 H41 N6'
_chemical_formula_moiety         'C31 H41 N6'
_chemical_formula_weight         497.71
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   13.9813(9)
_cell_length_b                   15.2468(6)
_cell_length_c                   15.1459(8)
_cell_angle_alpha                90.0000
_cell_angle_beta                 112.159(7)
_cell_angle_gamma                90.0000
_cell_volume                     2990.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5694
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      25.65
_cell_measurement_temperature    150
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.105
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1076.00
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.288
_exptl_absorpt_correction_T_max  0.999

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      150
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            23865
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.672
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             6832
_reflns_number_gt                3802
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1350
_refine_ls_R_factor_gt           0.0643
_refine_ls_wR_factor_ref         0.2147
_refine_ls_wR_factor_gt          0.1739
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         6832
_refine_ls_number_parameters     336
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1067P)²+0.5290P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.53
_refine_diff_density_min         -0.43
_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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.34153(19) 0.30917(16) 0.16720(16) 0.0564(6) Uani 1 1 d . . . . .
N2 N 0.53903(18) 0.50110(15) 0.35847(15) 0.0543(6) Uani 1 1 d . . . . .
N3 N 0.65046(19) 0.36819(15) -0.20692(16) 0.0583(6) Uani 1 1 d . . . . .
N4 N 0.8592(2) 0.56089(17) -0.01468(18) 0.0651(7) Uani 1 1 d . . . . .
N5 N 0.49317(15) 0.70500(13) 0.50189(13) 0.0407(5) Uani 1 1 d . . . . .
N6 N 0.64503(15) 0.66625(12) 0.59813(13) 0.0398(5) Uani 1 1 d . . . . .
C1 C 0.4074(2) 0.35946(16) 0.18027(15) 0.0404(6) Uani 1 1 d . . . . .
C2 C 0.48953(18) 0.42024(14) 0.19880(15) 0.0356(5) Uani 1 1 d . . . . .
C3 C 0.51808(19) 0.46567(16) 0.28670(17) 0.0408(6) Uani 1 1 d . . . . .
C4 C 0.54305(17) 0.43043(14) 0.13643(15) 0.0328(5) Uani 1 1 d . . . . .
C5 C 0.63069(18) 0.48608(14) 0.15894(15) 0.0366(5) Uani 1 1 d . . . . .
H5 H 0.654844 0.516981 0.217751 0.044 Uiso 1 1 calc R U . . .
C6 C 0.68101(18) 0.49601(15) 0.09747(16) 0.0379(6) Uani 1 1 d . . . . .
H6 H 0.739120 0.533902 0.114356 0.046 Uiso 1 1 calc R U . . .
C7 C 0.64812(17) 0.45097(14) 0.00944(15) 0.0340(5) Uani 1 1 d . . . . .
C8 C 0.56170(18) 0.39477(14) -0.01255(15) 0.0360(5) Uani 1 1 d . . . . .
H8 H 0.538318 0.363378 -0.071050 0.043 Uiso 1 1 calc R U . . .
C9 C 0.51108(17) 0.38453(14) 0.04821(15) 0.0346(5) Uani 1 1 d . . . . .
H9 H 0.453479 0.346074 0.031284 0.042 Uiso 1 1 calc R U . . .
C10 C 0.67247(19) 0.41105(16) -0.13928(18) 0.0421(6) Uani 1 1 d . . . . .
C11 C 0.70040(18) 0.46116(15) -0.05459(16) 0.0392(6) Uani 1 1 d . . . . .
C12 C 0.7881(2) 0.51607(17) -0.03310(18) 0.0471(6) Uani 1 1 d . . . . .
C13 C 0.56085(19) 0.63970(16) 0.52679(16) 0.0420(6) Uani 1 1 d . . . . .
H13 H 0.550673 0.583224 0.498215 0.050 Uiso 1 1 calc R U . . .
C14 C 0.53594(19) 0.77609(16) 0.55879(17) 0.0441(6) Uani 1 1 d . . . . .
H14 H 0.504613 0.831813 0.556265 0.053 Uiso 1 1 calc R U . . .
C15 C 0.63079(19) 0.75172(16) 0.61884(17) 0.0423(6) Uani 1 1 d . . . . .
H15 H 0.678946 0.787157 0.666697 0.051 Uiso 1 1 calc R U . . .
C16 C 0.38677(19) 0.70004(18) 0.43035(16) 0.0483(7) Uani 1 1 d . . . . .
H16A H 0.386026 0.663788 0.375868 0.058 Uiso 1 1 calc R U . . .
H16B H 0.362788 0.759661 0.406186 0.058 Uiso 1 1 calc R U . . .
C17 C 0.31391(19) 0.66068(16) 0.47234(17) 0.0469(6) Uani 1 1 d . . . . .
H17A H 0.336407 0.600044 0.493474 0.056 Uiso 1 1 calc R U . . .
H17B H 0.243807 0.657491 0.422037 0.056 Uiso 1 1 calc R U . . .
C18 C 0.30885(19) 0.71257(16) 0.55639(17) 0.0452(6) Uani 1 1 d . . . . .
H18A H 0.377409 0.710697 0.609128 0.054 Uiso 1 1 calc R U . . .
H18B H 0.293300 0.774624 0.537042 0.054 Uiso 1 1 calc R U . . .
C19 C 0.2287(2) 0.67878(18) 0.59241(18) 0.0534(7) Uani 1 1 d . . . . .
H19A H 0.159659 0.684521 0.540960 0.064 Uiso 1 1 calc R U . . .
H19B H 0.241412 0.615619 0.607401 0.064 Uiso 1 1 calc R U . . .
C20 C 0.2282(2) 0.72578(18) 0.67950(19) 0.0569(7) Uani 1 1 d . . . . .
H20A H 0.297570 0.720741 0.730645 0.068 Uiso 1 1 calc R U . . .
H20B H 0.214594 0.788813 0.664226 0.068 Uiso 1 1 calc R U . . .
C21 C 0.1494(3) 0.6914(2) 0.7163(2) 0.0724(9) Uani 1 1 d . . . . .
H21A H 0.155624 0.626798 0.721555 0.087 Uiso 1 1 calc R U . . .
H21B H 0.079530 0.705291 0.669348 0.087 Uiso 1 1 calc R U . . .
C22 C 0.1598(3) 0.7284(2) 0.8117(3) 0.0896(12) Uani 1 1 d . . . . .
H22A H 0.232082 0.720336 0.856618 0.108 Uiso 1 1 calc R U . . .
H22B H 0.146263 0.792261 0.804518 0.108 Uiso 1 1 calc R U . . .
C23 C 0.0918(4) 0.6897(3) 0.8531(3) 0.1061(14) Uani 1 1 d . . . . .
H23A H 0.107830 0.713739 0.917113 0.127 Uiso 1 1 calc R U . . .
H23B H 0.101539 0.625956 0.857247 0.127 Uiso 1 1 calc R U . . .
H23C H 0.019914 0.703186 0.813004 0.127 Uiso 1 1 calc R U . . .
C24 C 0.73914(19) 0.61396(18) 0.64779(18) 0.0493(6) Uani 1 1 d . . . . .
H24A H 0.721979 0.550821 0.637635 0.059 Uiso 1 1 calc R U . . .
H24B H 0.763699 0.625678 0.717107 0.059 Uiso 1 1 calc R U . . .
C25 C 0.82499(19) 0.63498(16) 0.61282(17) 0.0460(6) Uani 1 1 d . . . . .
H25A H 0.890063 0.609015 0.657696 0.055 Uiso 1 1 calc R U . . .
H25B H 0.834418 0.699391 0.614176 0.055 Uiso 1 1 calc R U . . .
C26 C 0.80650(19) 0.60216(16) 0.51303(18) 0.0453(6) Uani 1 1 d . . . . .
H26A H 0.743635 0.630504 0.467259 0.054 Uiso 1 1 calc R U . . .
H26B H 0.793981 0.538129 0.510414 0.054 Uiso 1 1 calc R U . . .
C27 C 0.89671(19) 0.62076(16) 0.48285(18) 0.0448(6) Uani 1 1 d . . . . .
H27A H 0.907038 0.685020 0.483208 0.054 Uiso 1 1 calc R U . . .
H27B H 0.959985 0.594923 0.530750 0.054 Uiso 1 1 calc R U . . .
C28 C 0.88376(19) 0.58564(17) 0.38539(19) 0.0478(6) Uani 1 1 d . . . . .
H28A H 0.823094 0.614241 0.336811 0.057 Uiso 1 1 calc R U . . .
H28B H 0.869420 0.521940 0.383566 0.057 Uiso 1 1 calc R U . . .
C29 C 0.97722(19) 0.60030(16) 0.35935(17) 0.0448(6) Uani 1 1 d . . . . .
H29A H 0.991633 0.664011 0.361727 0.054 Uiso 1 1 calc R U . . .
H29B H 1.037703 0.571610 0.408069 0.054 Uiso 1 1 calc R U . . .
C30 C 0.9661(2) 0.56616(18) 0.26236(19) 0.0521(7) Uani 1 1 d . . . . .
H30A H 0.910838 0.599548 0.212917 0.063 Uiso 1 1 calc R U . . .
H30B H 0.944350 0.503944 0.257177 0.063 Uiso 1 1 calc R U . . .
C31 C 1.0644(2) 0.57293(19) 0.2428(2) 0.0572(7) Uani 1 1 d . . . . .
H31A H 1.051790 0.550841 0.178629 0.069 Uiso 1 1 calc R U . . .
H31B H 1.118757 0.537933 0.289795 0.069 Uiso 1 1 calc R U . . .
H31C H 1.086288 0.634384 0.247401 0.069 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2016/4 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.4'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.156(3) . ?
N2 C3 1.149(3) . ?
N3 C10 1.155(3) . ?
N4 C12 1.152(3) . ?
N5 C13 1.327(3) . ?
N5 C14 1.373(3) . ?
N5 C16 1.475(3) . ?
N6 C13 1.326(3) . ?
N6 C15 1.372(3) . ?
N6 C24 1.478(3) . ?
C1 C2 1.419(4) . ?
C2 C4 1.418(3) . ?
C2 C3 1.418(3) . ?
C4 C5 1.422(3) . ?
C4 C9 1.423(3) . ?
C5 C6 1.371(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.414(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.415(3) . ?
C7 C11 1.426(3) . ?
C8 C9 1.365(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.416(3) . ?
C11 C12 1.417(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.347(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.514(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.523(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.509(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.504(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.504(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.505(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.449(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.518(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.519(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.521(3) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.516(3) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.517(3) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.510(3) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.515(4) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?

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
C13 N5 C14 108.6(2) . . ?
C13 N5 C16 125.7(2) . . ?
C14 N5 C16 125.5(2) . . ?
C13 N6 C15 108.4(2) . . ?
C13 N6 C24 126.6(2) . . ?
C15 N6 C24 125.0(2) . . ?
N1 C1 C2 178.5(3) . . ?
C4 C2 C3 122.7(2) . . ?
C4 C2 C1 122.08(19) . . ?
C3 C2 C1 115.15(19) . . ?
N2 C3 C2 178.0(3) . . ?
C2 C4 C5 121.96(19) . . ?
C2 C4 C9 120.9(2) . . ?
C5 C4 C9 117.10(19) . . ?
C6 C5 C4 121.3(2) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 121.3(2) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C6 C7 C8 117.48(19) . . ?
C6 C7 C11 121.4(2) . . ?
C8 C7 C11 121.1(2) . . ?
C9 C8 C7 121.6(2) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C4 121.2(2) . . ?
C8 C9 H9 119.4 . . ?
C4 C9 H9 119.4 . . ?
N3 C10 C11 178.2(3) . . ?
C10 C11 C12 116.5(2) . . ?
C10 C11 C7 121.4(2) . . ?
C12 C11 C7 121.9(2) . . ?
N4 C12 C11 179.3(3) . . ?
N6 C13 N5 108.7(2) . . ?
N6 C13 H13 125.6 . . ?
N5 C13 H13 125.6 . . ?
C15 C14 N5 106.9(2) . . ?
C15 C14 H14 126.5 . . ?
N5 C14 H14 126.5 . . ?
C14 C15 N6 107.4(2) . . ?
C14 C15 H15 126.3 . . ?
N6 C15 H15 126.3 . . ?
N5 C16 C17 111.3(2) . . ?
N5 C16 H16A 109.4 . . ?
C17 C16 H16A 109.4 . . ?
N5 C16 H16B 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C16 C17 C18 113.3(2) . . ?
C16 C17 H17A 108.9 . . ?
C18 C17 H17A 108.9 . . ?
C16 C17 H17B 108.9 . . ?
C18 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
C19 C18 C17 113.5(2) . . ?
C19 C18 H18A 108.9 . . ?
C17 C18 H18A 108.9 . . ?
C19 C18 H18B 108.9 . . ?
C17 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C20 C19 C18 113.9(2) . . ?
C20 C19 H19A 108.8 . . ?
C18 C19 H19A 108.8 . . ?
C20 C19 H19B 108.8 . . ?
C18 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C21 C20 C19 114.0(2) . . ?
C21 C20 H20A 108.8 . . ?
C19 C20 H20A 108.8 . . ?
C21 C20 H20B 108.8 . . ?
C19 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
C20 C21 C22 113.9(3) . . ?
C20 C21 H21A 108.8 . . ?
C22 C21 H21A 108.8 . . ?
C20 C21 H21B 108.8 . . ?
C22 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
C23 C22 C21 114.9(3) . . ?
C23 C22 H22A 108.5 . . ?
C21 C22 H22A 108.5 . . ?
C23 C22 H22B 108.5 . . ?
C21 C22 H22B 108.5 . . ?
H22A C22 H22B 107.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N6 C24 C25 112.2(2) . . ?
N6 C24 H24A 109.2 . . ?
C25 C24 H24A 109.2 . . ?
N6 C24 H24B 109.2 . . ?
C25 C24 H24B 109.2 . . ?
H24A C24 H24B 107.9 . . ?
C24 C25 C26 114.7(2) . . ?
C24 C25 H25A 108.6 . . ?
C26 C25 H25A 108.6 . . ?
C24 C25 H25B 108.6 . . ?
C26 C25 H25B 108.6 . . ?
H25A C25 H25B 107.6 . . ?
C25 C26 C27 112.8(2) . . ?
C25 C26 H26A 109.0 . . ?
C27 C26 H26A 109.0 . . ?
C25 C26 H26B 109.0 . . ?
C27 C26 H26B 109.0 . . ?
H26A C26 H26B 107.8 . . ?
C28 C27 C26 114.8(2) . . ?
C28 C27 H27A 108.6 . . ?
C26 C27 H27A 108.6 . . ?
C28 C27 H27B 108.6 . . ?
C26 C27 H27B 108.6 . . ?
H27A C27 H27B 107.6 . . ?
C27 C28 C29 113.8(2) . . ?
C27 C28 H28A 108.8 . . ?
C29 C28 H28A 108.8 . . ?
C27 C28 H28B 108.8 . . ?
C29 C28 H28B 108.8 . . ?
H28A C28 H28B 107.7 . . ?
C30 C29 C28 114.8(2) . . ?
C30 C29 H29A 108.6 . . ?
C28 C29 H29A 108.6 . . ?
C30 C29 H29B 108.6 . . ?
C28 C29 H29B 108.6 . . ?
H29A C29 H29B 107.5 . . ?
C29 C30 C31 113.5(2) . . ?
C29 C30 H30A 108.9 . . ?
C31 C30 H30A 108.9 . . ?
C29 C30 H30B 108.9 . . ?
C31 C30 H30B 108.9 . . ?
H30A C30 H30B 107.7 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 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
C3 C2 C4 C5 1.2(3) . . . . ?
C1 C2 C4 C5 -174.8(2) . . . . ?
C3 C2 C4 C9 -179.1(2) . . . . ?
C1 C2 C4 C9 4.9(3) . . . . ?
C2 C4 C5 C6 -179.3(2) . . . . ?
C9 C4 C5 C6 1.0(3) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
C5 C6 C7 C8 -0.4(3) . . . . ?
C5 C6 C7 C11 -180.0(2) . . . . ?
C6 C7 C8 C9 0.5(3) . . . . ?
C11 C7 C8 C9 -180.0(2) . . . . ?
C7 C8 C9 C4 0.2(3) . . . . ?
C2 C4 C9 C8 179.3(2) . . . . ?
C5 C4 C9 C8 -1.0(3) . . . . ?
C6 C7 C11 C10 175.1(2) . . . . ?
C8 C7 C11 C10 -4.4(3) . . . . ?
C6 C7 C11 C12 0.5(3) . . . . ?
C8 C7 C11 C12 -179.0(2) . . . . ?
C15 N6 C13 N5 -0.5(3) . . . . ?
C24 N6 C13 N5 179.6(2) . . . . ?
C14 N5 C13 N6 0.5(3) . . . . ?
C16 N5 C13 N6 -175.0(2) . . . . ?
C13 N5 C14 C15 -0.3(3) . . . . ?
C16 N5 C14 C15 175.3(2) . . . . ?
N5 C14 C15 N6 0.0(3) . . . . ?
C13 N6 C15 C14 0.3(3) . . . . ?
C24 N6 C15 C14 -179.8(2) . . . . ?
C13 N5 C16 C17 81.8(3) . . . . ?
C14 N5 C16 C17 -93.1(3) . . . . ?
N5 C16 C17 C18 59.6(3) . . . . ?
C16 C17 C18 C19 174.4(2) . . . . ?
C17 C18 C19 C20 176.1(2) . . . . ?
C18 C19 C20 C21 -179.2(2) . . . . ?
C19 C20 C21 C22 170.8(3) . . . . ?
C20 C21 C22 C23 -173.9(3) . . . . ?
C13 N6 C24 C25 100.1(3) . . . . ?
C15 N6 C24 C25 -79.7(3) . . . . ?
N6 C24 C25 C26 -71.2(3) . . . . ?
C24 C25 C26 C27 -177.2(2) . . . . ?
C25 C26 C27 C28 177.4(2) . . . . ?
C26 C27 C28 C29 -176.6(2) . . . . ?
C27 C28 C29 C30 -179.8(2) . . . . ?
C28 C29 C30 C31 -173.8(2) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_TOA_TCNQ
_database_code_depnum_ccdc_archive 'CCDC 2457383'
loop_
_audit_author_name
_audit_author_address
'Ruifeng Shu'
;The University of Osaka
Japan
;
_audit_update_record             
;
2025-06-07 deposited with the CCDC.	2025-09-24 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C44 H72 N5'
_chemical_formula_moiety         'C44 H72 N5'
_chemical_formula_weight         671.09
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   11.0521(2)
_cell_length_b                   13.7460(3)
_cell_length_c                   15.6376(3)
_cell_angle_alpha                69.620(2)
_cell_angle_beta                 76.6492(17)
_cell_angle_gamma                89.3974(16)
_cell_volume                     2160.43(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    14557
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      29.09
_cell_measurement_temperature    150
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.032
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             742.00
_exptl_absorpt_coefficient_mu    0.060
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.658
_exptl_absorpt_correction_T_max  0.999

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      150
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            40071
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_theta_max         29.534
_diffrn_reflns_theta_min         1.899
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             10785
_reflns_number_gt                7168
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1686
_refine_ls_wR_factor_gt          0.1399
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         10785
_refine_ls_number_parameters     442
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1026P)²+0.0063P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.24
_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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.18795(12) 0.34698(11) 0.20880(9) 0.0434(3) Uani 1 1 d . . . . .
N2 N 0.56579(12) 0.30610(11) 0.25492(9) 0.0409(3) Uani 1 1 d . . . . .
N3 N 0.50062(12) 0.48966(11) -0.37144(9) 0.0383(3) Uani 1 1 d . . . . .
N4 N 0.86093(11) 0.40459(10) -0.30909(9) 0.0371(3) Uani 1 1 d . . . . .
N5 N 0.81543(9) 0.36800(8) 0.40145(7) 0.0214(2) Uani 1 1 d . . . . .
C1 C 0.29321(13) 0.35112(11) 0.17735(9) 0.0300(3) Uani 1 1 d . . . . .
C2 C 0.50125(13) 0.32851(11) 0.20405(9) 0.0292(3) Uani 1 1 d . . . . .
C3 C 0.42395(12) 0.35500(11) 0.13905(9) 0.0272(3) Uani 1 1 d . . . . .
C4 C 0.47499(12) 0.37793(10) 0.04195(9) 0.0251(3) Uani 1 1 d . . . . .
C5 C 0.39967(12) 0.40246(11) -0.02421(9) 0.0264(3) Uani 1 1 d . . . . .
H5 H 0.312174 0.403971 -0.002833 0.032 Uiso 1 1 calc R U . . .
C6 C 0.45044(12) 0.42388(11) -0.11775(9) 0.0261(3) Uani 1 1 d . . . . .
H6 H 0.397576 0.441121 -0.160100 0.031 Uiso 1 1 calc R U . . .
C7 C 0.60579(12) 0.37654(11) 0.00591(9) 0.0278(3) Uani 1 1 d . . . . .
H7 H 0.659169 0.361398 0.047850 0.033 Uiso 1 1 calc R U . . .
C8 C 0.65581(12) 0.39642(11) -0.08719(9) 0.0272(3) Uani 1 1 d . . . . .
H8 H 0.743102 0.393835 -0.108576 0.033 Uiso 1 1 calc R U . . .
C9 C 0.58022(12) 0.42099(10) -0.15321(9) 0.0245(3) Uani 1 1 d . . . . .
C10 C 0.56035(13) 0.46696(11) -0.31696(9) 0.0283(3) Uani 1 1 d . . . . .
C11 C 0.75923(13) 0.42065(11) -0.28197(9) 0.0276(3) Uani 1 1 d . . . . .
C12 C 0.63288(12) 0.43777(11) -0.24938(9) 0.0260(3) Uani 1 1 d . . . . .
C13 C 0.91146(12) 0.28755(10) 0.40488(9) 0.0239(3) Uani 1 1 d . . . . .
H13A H 0.926801 0.261692 0.468671 0.029 Uiso 1 1 calc R U . . .
H13B H 0.990797 0.322401 0.360131 0.029 Uiso 1 1 calc R U . . .
C14 C 0.87590(13) 0.19451(11) 0.38183(10) 0.0293(3) Uani 1 1 d . . . . .
H14A H 0.803795 0.152828 0.431472 0.035 Uiso 1 1 calc R U . . .
H14B H 0.850692 0.219377 0.321467 0.035 Uiso 1 1 calc R U . . .
C15 C 0.98447(13) 0.12635(11) 0.37464(10) 0.0292(3) Uani 1 1 d . . . . .
H15A H 1.057233 0.169305 0.326752 0.035 Uiso 1 1 calc R U . . .
H15B H 1.007702 0.100391 0.435740 0.035 Uiso 1 1 calc R U . . .
C16 C 0.95546(13) 0.03385(11) 0.34853(10) 0.0303(3) Uani 1 1 d . . . . .
H16A H 0.888682 -0.012878 0.399951 0.036 Uiso 1 1 calc R U . . .
H16B H 0.922942 0.059490 0.291309 0.036 Uiso 1 1 calc R U . . .
C17 C 1.06598(14) -0.02856(12) 0.33067(11) 0.0348(3) Uani 1 1 d . . . . .
H17A H 1.097967 -0.054456 0.388125 0.042 Uiso 1 1 calc R U . . .
H17B H 1.132965 0.018542 0.279745 0.042 Uiso 1 1 calc R U . . .
C18 C 1.03908(16) -0.12074(12) 0.30366(11) 0.0399(4) Uani 1 1 d . . . . .
H18A H 1.115633 -0.158365 0.297660 0.048 Uiso 1 1 calc R U . . .
H18B H 0.974063 -0.168920 0.355578 0.048 Uiso 1 1 calc R U . . .
C19 C 0.9967(2) -0.09440(15) 0.21406(13) 0.0591(5) Uani 1 1 d . . . . .
H19A H 1.060367 -0.044737 0.162223 0.071 Uiso 1 1 calc R U . . .
H19B H 0.918427 -0.058971 0.220596 0.071 Uiso 1 1 calc R U . . .
C20 C 0.9744(2) -0.18693(17) 0.18761(15) 0.0681(6) Uani 1 1 d . . . . .
H20A H 0.947161 -0.163601 0.128787 0.082 Uiso 1 1 calc R U . . .
H20B H 1.051915 -0.221565 0.179189 0.082 Uiso 1 1 calc R U . . .
H20C H 0.909756 -0.235820 0.237652 0.082 Uiso 1 1 calc R U . . .
C21 C 0.79763(12) 0.41930(10) 0.30196(8) 0.0233(3) Uani 1 1 d . . . . .
H21A H 0.766231 0.365086 0.282526 0.028 Uiso 1 1 calc R U . . .
H21B H 0.732897 0.469489 0.302982 0.028 Uiso 1 1 calc R U . . .
C22 C 0.91470(12) 0.47597(11) 0.22882(9) 0.0280(3) Uani 1 1 d . . . . .
H22A H 0.972945 0.424394 0.216768 0.034 Uiso 1 1 calc R U . . .
H22B H 0.956475 0.520044 0.253496 0.034 Uiso 1 1 calc R U . . .
C23 C 0.88507(12) 0.54396(11) 0.13676(9) 0.0277(3) Uani 1 1 d . . . . .
H23A H 0.846147 0.499451 0.110939 0.033 Uiso 1 1 calc R U . . .
H23B H 0.824227 0.593653 0.149312 0.033 Uiso 1 1 calc R U . . .
C24 C 1.00155(13) 0.60433(11) 0.06415(9) 0.0286(3) Uani 1 1 d . . . . .
H24A H 1.060318 0.554102 0.049779 0.034 Uiso 1 1 calc R U . . .
H24B H 1.042775 0.645350 0.091858 0.034 Uiso 1 1 calc R U . . .
C25 C 0.97580(14) 0.67784(12) -0.02753(10) 0.0358(4) Uani 1 1 d . . . . .
H25A H 0.937147 0.636379 -0.056202 0.043 Uiso 1 1 calc R U . . .
H25B H 0.914642 0.726339 -0.012776 0.043 Uiso 1 1 calc R U . . .
C26 C 1.09098(14) 0.74137(12) -0.09946(10) 0.0372(4) Uani 1 1 d . . . . .
H26A H 1.153818 0.692841 -0.111496 0.045 Uiso 1 1 calc R U . . .
H26B H 1.067418 0.778529 -0.159252 0.045 Uiso 1 1 calc R U . . .
C27 C 1.15107(16) 0.82056(13) -0.07103(12) 0.0457(4) Uani 1 1 d . . . . .
H27A H 1.088756 0.869555 -0.059234 0.055 Uiso 1 1 calc R U . . .
H27B H 1.175271 0.783763 -0.011424 0.055 Uiso 1 1 calc R U . . .
C28 C 1.26567(18) 0.88241(14) -0.14455(14) 0.0560(5) Uani 1 1 d . . . . .
H28A H 1.299755 0.931806 -0.122013 0.067 Uiso 1 1 calc R U . . .
H28B H 1.328804 0.834686 -0.155545 0.067 Uiso 1 1 calc R U . . .
H28C H 1.242209 0.920559 -0.203399 0.067 Uiso 1 1 calc R U . . .
C29 C 0.86279(12) 0.44997(10) 0.43383(9) 0.0228(3) Uani 1 1 d . . . . .
H29A H 0.865163 0.416647 0.500609 0.027 Uiso 1 1 calc R U . . .
H29B H 0.949355 0.474850 0.396879 0.027 Uiso 1 1 calc R U . . .
C30 C 0.78554(13) 0.54295(11) 0.42427(10) 0.0289(3) Uani 1 1 d . . . . .
H30A H 0.696423 0.518297 0.451902 0.035 Uiso 1 1 calc R U . . .
H30B H 0.795382 0.584248 0.356737 0.035 Uiso 1 1 calc R U . . .
C31 C 0.82344(13) 0.61241(10) 0.47293(9) 0.0266(3) Uani 1 1 d . . . . .
H31A H 0.822433 0.569641 0.538813 0.032 Uiso 1 1 calc R U . . .
H31B H 0.909593 0.643506 0.440731 0.032 Uiso 1 1 calc R U . . .
C32 C 0.73611(13) 0.69873(11) 0.47192(10) 0.0285(3) Uani 1 1 d . . . . .
H32A H 0.649008 0.667930 0.492556 0.034 Uiso 1 1 calc R U . . .
H32B H 0.748911 0.748132 0.406451 0.034 Uiso 1 1 calc R U . . .
C33 C 0.75336(13) 0.75897(11) 0.53406(10) 0.0304(3) Uani 1 1 d . . . . .
H33A H 0.746841 0.709188 0.598667 0.036 Uiso 1 1 calc R U . . .
H33B H 0.838229 0.794626 0.510394 0.036 Uiso 1 1 calc R U . . .
C34 C 0.65895(13) 0.83906(11) 0.53763(10) 0.0307(3) Uani 1 1 d . . . . .
H34A H 0.574070 0.803506 0.560071 0.037 Uiso 1 1 calc R U . . .
H34B H 0.666578 0.889500 0.473127 0.037 Uiso 1 1 calc R U . . .
C35 C 0.67397(15) 0.89835(12) 0.60105(11) 0.0371(4) Uani 1 1 d . . . . .
H35A H 0.676089 0.847744 0.663711 0.044 Uiso 1 1 calc R U . . .
H35B H 0.754836 0.940606 0.574414 0.044 Uiso 1 1 calc R U . . .
C36 C 0.57071(18) 0.96915(15) 0.61275(14) 0.0543(5) Uani 1 1 d . . . . .
H36A H 0.585508 1.004999 0.654110 0.065 Uiso 1 1 calc R U . . .
H36B H 0.569257 1.020633 0.551178 0.065 Uiso 1 1 calc R U . . .
H36C H 0.490453 0.927705 0.640539 0.065 Uiso 1 1 calc R U . . .
C37 C 0.68854(12) 0.31773(10) 0.46437(9) 0.0244(3) Uani 1 1 d . . . . .
H37A H 0.629806 0.372917 0.462323 0.029 Uiso 1 1 calc R U . . .
H37B H 0.657027 0.269887 0.438169 0.029 Uiso 1 1 calc R U . . .
C38 C 0.68778(12) 0.25719(11) 0.56680(9) 0.0284(3) Uani 1 1 d . . . . .
H38A H 0.736689 0.298696 0.589512 0.034 Uiso 1 1 calc R U . . .
H38B H 0.728155 0.191533 0.571400 0.034 Uiso 1 1 calc R U . . .
C39 C 0.55529(13) 0.23222(11) 0.62907(9) 0.0281(3) Uani 1 1 d . . . . .
H39A H 0.511639 0.297081 0.618419 0.034 Uiso 1 1 calc R U . . .
H39B H 0.509527 0.183884 0.611038 0.034 Uiso 1 1 calc R U . . .
C40 C 0.55344(14) 0.18311(12) 0.73318(9) 0.0321(3) Uani 1 1 d . . . . .
H40A H 0.581978 0.112083 0.745670 0.039 Uiso 1 1 calc R U . . .
H40B H 0.613365 0.224353 0.747794 0.039 Uiso 1 1 calc R U . . .
C41 C 0.42597(15) 0.17652(13) 0.79840(10) 0.0387(4) Uani 1 1 d . . . . .
H41A H 0.367710 0.130068 0.787879 0.046 Uiso 1 1 calc R U . . .
H41B H 0.394048 0.246573 0.782279 0.046 Uiso 1 1 calc R U . . .
C42 C 0.42755(16) 0.13610(13) 0.90187(10) 0.0449(4) Uani 1 1 d . . . . .
H42A H 0.451967 0.063578 0.919211 0.054 Uiso 1 1 calc R U . . .
H42B H 0.491947 0.178477 0.911020 0.054 Uiso 1 1 calc R U . . .
C43 C 0.30403(18) 0.13832(15) 0.96761(12) 0.0555(5) Uani 1 1 d . . . . .
H43A H 0.241592 0.089918 0.963696 0.067 Uiso 1 1 calc R U . . .
H43B H 0.275065 0.209230 0.946332 0.067 Uiso 1 1 calc R U . . .
C44 C 0.3106(2) 0.10830(18) 1.06990(13) 0.0754(7) Uani 1 1 d . . . . .
H44A H 0.228069 0.111253 1.108593 0.090 Uiso 1 1 calc R U . . .
H44B H 0.337143 0.037476 1.092105 0.090 Uiso 1 1 calc R U . . .
H44C H 0.370645 0.156892 1.074725 0.090 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2016/4 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.1472(18) . ?
N2 C2 1.1503(18) . ?
N3 C10 1.1529(17) . ?
N4 C11 1.1540(17) . ?
N5 C13 1.5207(16) . ?
N5 C37 1.5237(16) . ?
N5 C21 1.5267(16) . ?
N5 C29 1.5272(15) . ?
C1 C3 1.4244(19) . ?
C2 C3 1.4257(19) . ?
C3 C4 1.4135(18) . ?
C4 C5 1.4232(18) . ?
C4 C7 1.4278(18) . ?
C5 C6 1.3660(18) . ?
C5 H5 0.9500 . ?
C6 C9 1.4189(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.3616(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.4238(18) . ?
C8 H8 0.9500 . ?
C9 C12 1.4179(18) . ?
C10 C12 1.4176(19) . ?
C11 C12 1.4188(19) . ?
C13 C14 1.5222(18) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.5223(19) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.5221(19) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.514(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.520(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.503(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.506(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.5186(18) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.5255(18) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.5253(19) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.5267(19) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.525(2) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.520(2) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.523(2) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C30 1.5125(19) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.5257(18) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.5199(19) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.5217(18) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.515(2) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.5222(19) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.512(2) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 C38 1.5245(18) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 C39 1.5262(18) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 C40 1.5252(19) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 C41 1.519(2) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 C42 1.521(2) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 C43 1.515(2) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 C44 1.526(3) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?

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
C13 N5 C37 111.02(10) . . ?
C13 N5 C21 111.03(9) . . ?
C37 N5 C21 106.89(9) . . ?
C13 N5 C29 107.55(9) . . ?
C37 N5 C29 110.52(9) . . ?
C21 N5 C29 109.85(9) . . ?
N1 C1 C3 179.30(18) . . ?
N2 C2 C3 178.17(15) . . ?
C4 C3 C1 122.03(12) . . ?
C4 C3 C2 121.02(12) . . ?
C1 C3 C2 116.85(11) . . ?
C3 C4 C5 122.20(12) . . ?
C3 C4 C7 120.95(12) . . ?
C5 C4 C7 116.85(11) . . ?
C6 C5 C4 121.45(12) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C9 121.59(12) . . ?
C5 C6 H6 119.2 . . ?
C9 C6 H6 119.2 . . ?
C8 C7 C4 121.52(12) . . ?
C8 C7 H7 119.2 . . ?
C4 C7 H7 119.2 . . ?
C7 C8 C9 121.49(12) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C12 C9 C6 122.00(12) . . ?
C12 C9 C8 120.87(12) . . ?
C6 C9 C8 117.08(11) . . ?
N3 C10 C12 179.25(17) . . ?
N4 C11 C12 178.18(15) . . ?
C9 C12 C10 121.73(12) . . ?
C9 C12 C11 121.65(12) . . ?
C10 C12 C11 116.53(11) . . ?
N5 C13 C14 115.32(10) . . ?
N5 C13 H13A 108.4 . . ?
C14 C13 H13A 108.4 . . ?
N5 C13 H13B 108.4 . . ?
C14 C13 H13B 108.4 . . ?
H13A C13 H13B 107.5 . . ?
C15 C14 C13 111.07(11) . . ?
C15 C14 H14A 109.4 . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C16 C15 C14 113.33(11) . . ?
C16 C15 H15A 108.9 . . ?
C14 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C17 C16 C15 114.36(12) . . ?
C17 C16 H16A 108.7 . . ?
C15 C16 H16A 108.7 . . ?
C17 C16 H16B 108.7 . . ?
C15 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C16 C17 C18 115.13(13) . . ?
C16 C17 H17A 108.5 . . ?
C18 C17 H17A 108.5 . . ?
C16 C17 H17B 108.5 . . ?
C18 C17 H17B 108.5 . . ?
H17A C17 H17B 107.5 . . ?
C19 C18 C17 115.51(14) . . ?
C19 C18 H18A 108.4 . . ?
C17 C18 H18A 108.4 . . ?
C19 C18 H18B 108.4 . . ?
C17 C18 H18B 108.4 . . ?
H18A C18 H18B 107.5 . . ?
C18 C19 C20 114.30(16) . . ?
C18 C19 H19A 108.7 . . ?
C20 C19 H19A 108.7 . . ?
C18 C19 H19B 108.7 . . ?
C20 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 N5 114.64(10) . . ?
C22 C21 H21A 108.6 . . ?
N5 C21 H21A 108.6 . . ?
C22 C21 H21B 108.6 . . ?
N5 C21 H21B 108.6 . . ?
H21A C21 H21B 107.6 . . ?
C21 C22 C23 111.65(10) . . ?
C21 C22 H22A 109.3 . . ?
C23 C22 H22A 109.3 . . ?
C21 C22 H22B 109.3 . . ?
C23 C22 H22B 109.3 . . ?
H22A C22 H22B 108.0 . . ?
C24 C23 C22 111.97(11) . . ?
C24 C23 H23A 109.2 . . ?
C22 C23 H23A 109.2 . . ?
C24 C23 H23B 109.2 . . ?
C22 C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?
C23 C24 C25 113.96(11) . . ?
C23 C24 H24A 108.8 . . ?
C25 C24 H24A 108.8 . . ?
C23 C24 H24B 108.8 . . ?
C25 C24 H24B 108.8 . . ?
H24A C24 H24B 107.7 . . ?
C26 C25 C24 114.47(12) . . ?
C26 C25 H25A 108.6 . . ?
C24 C25 H25A 108.6 . . ?
C26 C25 H25B 108.6 . . ?
C24 C25 H25B 108.6 . . ?
H25A C25 H25B 107.6 . . ?
C27 C26 C25 115.09(13) . . ?
C27 C26 H26A 108.5 . . ?
C25 C26 H26A 108.5 . . ?
C27 C26 H26B 108.5 . . ?
C25 C26 H26B 108.5 . . ?
H26A C26 H26B 107.5 . . ?
C28 C27 C26 113.57(14) . . ?
C28 C27 H27A 108.9 . . ?
C26 C27 H27A 108.9 . . ?
C28 C27 H27B 108.9 . . ?
C26 C27 H27B 108.9 . . ?
H27A C27 H27B 107.7 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C30 C29 N5 114.64(10) . . ?
C30 C29 H29A 108.6 . . ?
N5 C29 H29A 108.6 . . ?
C30 C29 H29B 108.6 . . ?
N5 C29 H29B 108.6 . . ?
H29A C29 H29B 107.6 . . ?
C29 C30 C31 112.16(11) . . ?
C29 C30 H30A 109.2 . . ?
C31 C30 H30A 109.2 . . ?
C29 C30 H30B 109.2 . . ?
C31 C30 H30B 109.2 . . ?
H30A C30 H30B 107.9 . . ?
C32 C31 C30 111.51(11) . . ?
C32 C31 H31A 109.3 . . ?
C30 C31 H31A 109.3 . . ?
C32 C31 H31B 109.3 . . ?
C30 C31 H31B 109.3 . . ?
H31A C31 H31B 108.0 . . ?
C31 C32 C33 114.44(11) . . ?
C31 C32 H32A 108.7 . . ?
C33 C32 H32A 108.7 . . ?
C31 C32 H32B 108.7 . . ?
C33 C32 H32B 108.7 . . ?
H32A C32 H32B 107.6 . . ?
C34 C33 C32 113.44(11) . . ?
C34 C33 H33A 108.9 . . ?
C32 C33 H33A 108.9 . . ?
C34 C33 H33B 108.9 . . ?
C32 C33 H33B 108.9 . . ?
H33A C33 H33B 107.7 . . ?
C33 C34 C35 113.82(12) . . ?
C33 C34 H34A 108.8 . . ?
C35 C34 H34A 108.8 . . ?
C33 C34 H34B 108.8 . . ?
C35 C34 H34B 108.8 . . ?
H34A C34 H34B 107.7 . . ?
C36 C35 C34 113.30(13) . . ?
C36 C35 H35A 108.9 . . ?
C34 C35 H35A 108.9 . . ?
C36 C35 H35B 108.9 . . ?
C34 C35 H35B 108.9 . . ?
H35A C35 H35B 107.7 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C38 C37 N5 115.06(10) . . ?
C38 C37 H37A 108.5 . . ?
N5 C37 H37A 108.5 . . ?
C38 C37 H37B 108.5 . . ?
N5 C37 H37B 108.5 . . ?
H37A C37 H37B 107.5 . . ?
C37 C38 C39 111.52(11) . . ?
C37 C38 H38A 109.3 . . ?
C39 C38 H38A 109.3 . . ?
C37 C38 H38B 109.3 . . ?
C39 C38 H38B 109.3 . . ?
H38A C38 H38B 108.0 . . ?
C40 C39 C38 112.18(11) . . ?
C40 C39 H39A 109.2 . . ?
C38 C39 H39A 109.2 . . ?
C40 C39 H39B 109.2 . . ?
C38 C39 H39B 109.2 . . ?
H39A C39 H39B 107.9 . . ?
C41 C40 C39 113.79(12) . . ?
C41 C40 H40A 108.8 . . ?
C39 C40 H40A 108.8 . . ?
C41 C40 H40B 108.8 . . ?
C39 C40 H40B 108.8 . . ?
H40A C40 H40B 107.7 . . ?
C40 C41 C42 113.28(13) . . ?
C40 C41 H41A 108.9 . . ?
C42 C41 H41A 108.9 . . ?
C40 C41 H41B 108.9 . . ?
C42 C41 H41B 108.9 . . ?
H41A C41 H41B 107.7 . . ?
C43 C42 C41 114.16(15) . . ?
C43 C42 H42A 108.7 . . ?
C41 C42 H42A 108.7 . . ?
C43 C42 H42B 108.7 . . ?
C41 C42 H42B 108.7 . . ?
H42A C42 H42B 107.6 . . ?
C42 C43 C44 113.50(17) . . ?
C42 C43 H43A 108.9 . . ?
C44 C43 H43A 108.9 . . ?
C42 C43 H43B 108.9 . . ?
C44 C43 H43B 108.9 . . ?
H43A C43 H43B 107.7 . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 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
C1 C3 C4 C5 2.4(2) . . . . ?
C2 C3 C4 C5 178.65(13) . . . . ?
C1 C3 C4 C7 -177.03(13) . . . . ?
C2 C3 C4 C7 -0.8(2) . . . . ?
C3 C4 C5 C6 -179.63(13) . . . . ?
C7 C4 C5 C6 -0.2(2) . . . . ?
C4 C5 C6 C9 1.1(2) . . . . ?
C3 C4 C7 C8 178.65(13) . . . . ?
C5 C4 C7 C8 -0.8(2) . . . . ?
C4 C7 C8 C9 0.9(2) . . . . ?
C5 C6 C9 C12 176.66(13) . . . . ?
C5 C6 C9 C8 -1.0(2) . . . . ?
C7 C8 C9 C12 -177.68(13) . . . . ?
C7 C8 C9 C6 0.0(2) . . . . ?
C6 C9 C12 C10 5.4(2) . . . . ?
C8 C9 C12 C10 -177.07(13) . . . . ?
C6 C9 C12 C11 -171.11(13) . . . . ?
C8 C9 C12 C11 6.5(2) . . . . ?
C37 N5 C13 C14 54.60(13) . . . . ?
C21 N5 C13 C14 -64.16(13) . . . . ?
C29 N5 C13 C14 175.63(10) . . . . ?
N5 C13 C14 C15 172.56(10) . . . . ?
C13 C14 C15 C16 -178.13(11) . . . . ?
C14 C15 C16 C17 173.75(12) . . . . ?
C15 C16 C17 C18 -179.49(12) . . . . ?
C16 C17 C18 C19 61.72(19) . . . . ?
C17 C18 C19 C20 178.26(17) . . . . ?
C13 N5 C21 C22 -59.98(14) . . . . ?
C37 N5 C21 C22 178.80(11) . . . . ?
C29 N5 C21 C22 58.86(14) . . . . ?
N5 C21 C22 C23 -167.88(11) . . . . ?
C21 C22 C23 C24 177.84(12) . . . . ?
C22 C23 C24 C25 -177.01(12) . . . . ?
C23 C24 C25 C26 178.04(13) . . . . ?
C24 C25 C26 C27 -66.40(19) . . . . ?
C25 C26 C27 C28 180.00(14) . . . . ?
C13 N5 C29 C30 173.36(10) . . . . ?
C37 N5 C29 C30 -65.30(14) . . . . ?
C21 N5 C29 C30 52.41(14) . . . . ?
N5 C29 C30 C31 170.09(10) . . . . ?
C29 C30 C31 C32 -173.81(11) . . . . ?
C30 C31 C32 C33 169.46(12) . . . . ?
C31 C32 C33 C34 -175.64(12) . . . . ?
C32 C33 C34 C35 178.94(12) . . . . ?
C33 C34 C35 C36 -173.46(14) . . . . ?
C13 N5 C37 C38 55.86(14) . . . . ?
C21 N5 C37 C38 177.09(11) . . . . ?
C29 N5 C37 C38 -63.40(14) . . . . ?
N5 C37 C38 C39 166.19(11) . . . . ?
C37 C38 C39 C40 -173.23(12) . . . . ?
C38 C39 C40 C41 168.66(12) . . . . ?
C39 C40 C41 C42 -175.03(13) . . . . ?
C40 C41 C42 C43 174.61(14) . . . . ?
C41 C42 C43 C44 -173.99(16) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================

####################################################################### 
# 
# 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_DMDOA_TCNQ
_database_code_depnum_ccdc_archive 'CCDC 2457382'
loop_
_audit_author_name
_audit_author_address
'Ruifeng Shu'
;The University of Osaka
Japan
;
_audit_update_record             
;
2025-06-07 deposited with the CCDC.	2025-09-24 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C30 H44 N5'
_chemical_formula_moiety         'C30 H44 N5'
_chemical_formula_weight         474.71
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   11.9464(3)
_cell_length_b                   14.9849(5)
_cell_length_c                   17.3068(6)
_cell_angle_alpha                67.949(3)
_cell_angle_beta                 89.902(2)
_cell_angle_gamma                84.010(3)
_cell_volume                     2853.52(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12187
_cell_measurement_theta_min      2.14
_cell_measurement_theta_max      28.92
_cell_measurement_temperature    150
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.105
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1036.00
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.226
_exptl_absorpt_correction_T_max  0.999

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      150
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            55497
_diffrn_reflns_av_unetI/netI     0.0878
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_theta_max         29.476
_diffrn_reflns_theta_min         2.093
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.899
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             14269
_reflns_number_gt                7923
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1363
_refine_ls_R_factor_gt           0.0613
_refine_ls_wR_factor_ref         0.1878
_refine_ls_wR_factor_gt          0.1536
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         14269
_refine_ls_number_parameters     631
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0946P)²+0.0242P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.26
_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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.93367(14) 0.37203(13) 0.42491(12) 0.0443(5) Uani 1 1 d . . . . .
N2 N 0.68709(15) 0.57604(12) 0.24610(10) 0.0393(4) Uani 1 1 d . . . . .
N3 N 0.75884(18) -0.06766(14) 0.26896(11) 0.0517(5) Uani 1 1 d . . . . .
N4 N 0.52757(16) 0.14218(13) 0.07773(11) 0.0456(5) Uani 1 1 d . . . . .
N5 N 0.72047(14) 0.30719(12) 0.55323(10) 0.0388(4) Uani 1 1 d . . . . .
N6 N 0.47548(14) 0.53783(13) 0.37871(11) 0.0416(4) Uani 1 1 d . . . . .
N7 N 0.49642(15) -0.08280(13) 0.36242(11) 0.0448(5) Uani 1 1 d . . . . .
N8 N 0.26715(16) 0.15003(14) 0.18580(13) 0.0548(5) Uani 1 1 d . . . . .
N9 N 1.24495(11) 0.34388(10) 0.55775(9) 0.0243(3) Uani 1 1 d . . . . .
N10 N 0.58007(12) 0.17133(10) 0.81691(9) 0.0247(3) Uani 1 1 d . . . . .
C1 C 0.86535(15) 0.38325(14) 0.37417(12) 0.0291(4) Uani 1 1 d . . . . .
C2 C 0.72779(15) 0.49691(15) 0.27518(11) 0.0280(4) Uani 1 1 d . . . . .
C3 C 0.77979(14) 0.39985(13) 0.31180(11) 0.0247(4) Uani 1 1 d . . . . .
C4 C 0.75325(14) 0.32664(13) 0.28394(11) 0.0237(4) Uani 1 1 d . . . . .
C5 C 0.81182(14) 0.23193(13) 0.31585(11) 0.0272(4) Uani 1 1 d . . . . .
H5 H 0.870684 0.217695 0.355193 0.033 Uiso 1 1 calc R U . . .
C6 C 0.78368(15) 0.16139(13) 0.29009(11) 0.0271(4) Uani 1 1 d . . . . .
H6 H 0.823372 0.099923 0.312478 0.033 Uiso 1 1 calc R U . . .
C7 C 0.66670(14) 0.34560(13) 0.22202(11) 0.0266(4) Uani 1 1 d . . . . .
H7 H 0.628187 0.407467 0.198618 0.032 Uiso 1 1 calc R U . . .
C8 C 0.63877(15) 0.27529(13) 0.19609(11) 0.0270(4) Uani 1 1 d . . . . .
H8 H 0.581548 0.290221 0.155390 0.032 Uiso 1 1 calc R U . . .
C9 C 0.69474(14) 0.17996(13) 0.22960(10) 0.0235(4) Uani 1 1 d . . . . .
C10 C 0.71625(17) 0.01067(15) 0.23915(12) 0.0339(5) Uani 1 1 d . . . . .
C11 C 0.58762(17) 0.12707(14) 0.13416(12) 0.0313(5) Uani 1 1 d . . . . .
C12 C 0.66428(15) 0.10702(13) 0.20289(11) 0.0270(4) Uani 1 1 d . . . . .
C13 C 0.65528(16) 0.33280(13) 0.49803(12) 0.0277(4) Uani 1 1 d . . . . .
C14 C 0.52174(16) 0.46018(15) 0.40295(12) 0.0298(4) Uani 1 1 d . . . . .
C15 C 0.57421(15) 0.36345(13) 0.43013(11) 0.0266(4) Uani 1 1 d . . . . .
C16 C 0.53585(14) 0.29697(13) 0.39841(11) 0.0239(4) Uani 1 1 d . . . . .
C17 C 0.58235(15) 0.19926(13) 0.42806(11) 0.0277(4) Uani 1 1 d . . . . .
H17 H 0.639219 0.177842 0.469628 0.033 Uiso 1 1 calc R U . . .
C18 C 0.54609(15) 0.13520(13) 0.39736(11) 0.0280(4) Uani 1 1 d . . . . .
H18 H 0.579043 0.071281 0.418124 0.034 Uiso 1 1 calc R U . . .
C19 C 0.44667(15) 0.32575(13) 0.33655(11) 0.0277(4) Uani 1 1 d . . . . .
H19 H 0.412989 0.389444 0.316536 0.033 Uiso 1 1 calc R U . . .
C20 C 0.40977(15) 0.26209(13) 0.30615(11) 0.0279(4) Uani 1 1 d . . . . .
H20 H 0.351003 0.283034 0.266064 0.033 Uiso 1 1 calc R U . . .
C21 C 0.45893(14) 0.16436(13) 0.33425(11) 0.0259(4) Uani 1 1 d . . . . .
C22 C 0.46385(16) -0.00136(16) 0.33484(12) 0.0320(5) Uani 1 1 d . . . . .
C23 C 0.33654(17) 0.12709(14) 0.23779(13) 0.0355(5) Uani 1 1 d . . . . .
C24 C 0.42241(15) 0.09822(14) 0.30181(11) 0.0288(4) Uani 1 1 d . . . . .
C25 C 1.36625(15) 0.30581(14) 0.58139(12) 0.0329(5) Uani 1 1 d . . . . .
H25A H 1.373555 0.236289 0.605261 0.039 Uiso 1 1 calc R U . . .
H25B H 1.410230 0.326923 0.532609 0.039 Uiso 1 1 calc R U . . .
H25C H 1.392640 0.329842 0.621449 0.039 Uiso 1 1 calc R U . . .
C26 C 1.23614(16) 0.45174(13) 0.52094(12) 0.0307(4) Uani 1 1 d . . . . .
H26A H 1.158873 0.477439 0.505394 0.037 Uiso 1 1 calc R U . . .
H26B H 1.263137 0.475084 0.561282 0.037 Uiso 1 1 calc R U . . .
H26C H 1.280727 0.472165 0.472441 0.037 Uiso 1 1 calc R U . . .
C27 C 1.20327(15) 0.30869(13) 0.49280(11) 0.0275(4) Uani 1 1 d . . . . .
H27A H 1.237701 0.342466 0.440579 0.033 Uiso 1 1 calc R U . . .
H27B H 1.122590 0.326923 0.484098 0.033 Uiso 1 1 calc R U . . .
C28 C 1.22614(16) 0.20084(14) 0.51289(11) 0.0303(4) Uani 1 1 d . . . . .
H28A H 1.203538 0.165505 0.569063 0.036 Uiso 1 1 calc R U . . .
H28B H 1.306200 0.183434 0.510408 0.036 Uiso 1 1 calc R U . . .
C29 C 1.16165(16) 0.17288(14) 0.45134(12) 0.0315(5) Uani 1 1 d . . . . .
H29A H 1.081646 0.188536 0.455794 0.038 Uiso 1 1 calc R U . . .
H29B H 1.181548 0.211499 0.395207 0.038 Uiso 1 1 calc R U . . .
C30 C 1.18409(16) 0.06673(14) 0.46456(12) 0.0321(5) Uani 1 1 d . . . . .
H30A H 1.170282 0.027927 0.522068 0.038 Uiso 1 1 calc R U . . .
H30B H 1.262843 0.052266 0.455286 0.038 Uiso 1 1 calc R U . . .
C31 C 1.11195(16) 0.03797(14) 0.40751(12) 0.0335(5) Uani 1 1 d . . . . .
H31A H 1.033320 0.050456 0.418277 0.040 Uiso 1 1 calc R U . . .
H31B H 1.123655 0.078672 0.350108 0.040 Uiso 1 1 calc R U . . .
C32 C 1.13615(18) -0.06731(15) 0.41762(13) 0.0393(5) Uani 1 1 d . . . . .
H32A H 1.130899 -0.107803 0.476022 0.047 Uiso 1 1 calc R U . . .
H32B H 1.212971 -0.078314 0.402226 0.047 Uiso 1 1 calc R U . . .
C33 C 1.05782(19) -0.09895(16) 0.36611(13) 0.0414(5) Uani 1 1 d . . . . .
H33A H 1.074618 -0.168148 0.380374 0.050 Uiso 1 1 calc R U . . .
H33B H 0.980764 -0.086989 0.380587 0.050 Uiso 1 1 calc R U . . .
C34 C 1.0674(2) -0.04734(18) 0.27314(14) 0.0552(7) Uani 1 1 d . . . . .
H34A H 1.016122 -0.070278 0.244053 0.066 Uiso 1 1 calc R U . . .
H34B H 1.049115 0.021126 0.258255 0.066 Uiso 1 1 calc R U . . .
H34C H 1.143020 -0.060077 0.258041 0.066 Uiso 1 1 calc R U . . .
C35 C 1.18111(15) 0.30992(14) 0.63775(11) 0.0290(4) Uani 1 1 d . . . . .
H35A H 1.184489 0.239891 0.657853 0.035 Uiso 1 1 calc R U . . .
H35B H 1.220679 0.325471 0.679162 0.035 Uiso 1 1 calc R U . . .
C36 C 1.05918(16) 0.35037(15) 0.63348(12) 0.0343(5) Uani 1 1 d . . . . .
H36A H 1.016604 0.334189 0.593804 0.041 Uiso 1 1 calc R U . . .
H36B H 1.053058 0.420361 0.615350 0.041 Uiso 1 1 calc R U . . .
C37 C 1.01238(18) 0.30631(16) 0.72059(13) 0.0413(5) Uani 1 1 d . . . . .
H37A H 1.019341 0.236439 0.737397 0.050 Uiso 1 1 calc R U . . .
H37B H 1.058375 0.320735 0.759630 0.050 Uiso 1 1 calc R U . . .
C38 C 0.89023(18) 0.34193(19) 0.72706(15) 0.0517(6) Uani 1 1 d . . . . .
H38A H 0.844936 0.330609 0.685881 0.062 Uiso 1 1 calc R U . . .
H38B H 0.865286 0.303388 0.781680 0.062 Uiso 1 1 calc R U . . .
C39 C 0.86777(18) 0.44775(19) 0.71456(14) 0.0501(6) Uani 1 1 d . . . . .
H39A H 0.787216 0.463721 0.716142 0.060 Uiso 1 1 calc R U . . .
H39B H 0.890812 0.486313 0.659327 0.060 Uiso 1 1 calc R U . . .
C40 C 0.92664(17) 0.47707(16) 0.77797(13) 0.0436(6) Uani 1 1 d . . . . .
H40A H 0.909833 0.434687 0.833741 0.052 Uiso 1 1 calc R U . . .
H40B H 1.007438 0.468284 0.772410 0.052 Uiso 1 1 calc R U . . .
C41 C 0.8915(2) 0.58097(18) 0.76750(15) 0.0582(7) Uani 1 1 d . . . . .
H41A H 0.811543 0.588118 0.776773 0.070 Uiso 1 1 calc R U . . .
H41B H 0.902863 0.622487 0.710267 0.070 Uiso 1 1 calc R U . . .
C42 C 0.9535(2) 0.6160(2) 0.82489(19) 0.0744(8) Uani 1 1 d . . . . .
H42A H 0.926023 0.682321 0.814041 0.089 Uiso 1 1 calc R U . . .
H42B H 0.941134 0.576809 0.881850 0.089 Uiso 1 1 calc R U . . .
H42C H 1.032632 0.611244 0.815215 0.089 Uiso 1 1 calc R U . . .
C43 C 0.62121(16) 0.21881(14) 0.73016(11) 0.0308(4) Uani 1 1 d . . . . .
H43A H 0.595325 0.286773 0.708910 0.037 Uiso 1 1 calc R U . . .
H43B H 0.702056 0.210074 0.731830 0.037 Uiso 1 1 calc R U . . .
H43C H 0.592464 0.189817 0.694466 0.037 Uiso 1 1 calc R U . . .
C44 C 0.62154(16) 0.06613(13) 0.84811(12) 0.0329(5) Uani 1 1 d . . . . .
H44A H 0.596161 0.034510 0.903432 0.039 Uiso 1 1 calc R U . . .
H44B H 0.592788 0.037926 0.811808 0.039 Uiso 1 1 calc R U . . .
H44C H 0.702380 0.058183 0.849173 0.039 Uiso 1 1 calc R U . . .
C45 C 0.45204(14) 0.18511(13) 0.81183(11) 0.0254(4) Uani 1 1 d . . . . .
H45A H 0.427105 0.254005 0.790740 0.030 Uiso 1 1 calc R U . . .
H45B H 0.426255 0.159887 0.771749 0.030 Uiso 1 1 calc R U . . .
C46 C 0.39630(15) 0.13678(14) 0.89376(11) 0.0296(4) Uani 1 1 d . . . . .
H46A H 0.429698 0.153808 0.936687 0.036 Uiso 1 1 calc R U . . .
H46B H 0.409545 0.066978 0.910537 0.036 Uiso 1 1 calc R U . . .
C47 C 0.26984(15) 0.16798(14) 0.88581(11) 0.0288(4) Uani 1 1 d . . . . .
H47A H 0.256800 0.237422 0.871436 0.035 Uiso 1 1 calc R U . . .
H47B H 0.237198 0.153754 0.841018 0.035 Uiso 1 1 calc R U . . .
C48 C 0.21198(15) 0.11660(15) 0.96628(12) 0.0334(5) Uani 1 1 d . . . . .
H48A H 0.222263 0.047512 0.978467 0.040 Uiso 1 1 calc R U . . .
H48B H 0.249041 0.127312 1.011371 0.040 Uiso 1 1 calc R U . . .
C49 C 0.08688(16) 0.14834(16) 0.96513(12) 0.0364(5) Uani 1 1 d . . . . .
H49A H 0.048852 0.136343 0.921085 0.044 Uiso 1 1 calc R U . . .
H49B H 0.075770 0.217492 0.952547 0.044 Uiso 1 1 calc R U . . .
C50 C 0.03401(17) 0.09556(17) 1.04784(13) 0.0443(6) Uani 1 1 d . . . . .
H50A H 0.080122 0.098883 1.092555 0.053 Uiso 1 1 calc R U . . .
H50B H 0.035560 0.027789 1.055897 0.053 Uiso 1 1 calc R U . . .
C51 C -0.08687(19) 0.1347(2) 1.05531(15) 0.0590(7) Uani 1 1 d . . . . .
H51A H -0.130856 0.141842 1.005865 0.071 Uiso 1 1 calc R U . . .
H51B H -0.119157 0.088076 1.103032 0.071 Uiso 1 1 calc R U . . .
C52 C -0.0953(2) 0.2312(2) 1.06524(17) 0.0698(8) Uani 1 1 d . . . . .
H52A H -0.172808 0.252444 1.069635 0.084 Uiso 1 1 calc R U . . .
H52B H -0.053293 0.224372 1.114779 0.084 Uiso 1 1 calc R U . . .
H52C H -0.064994 0.278149 1.017592 0.084 Uiso 1 1 calc R U . . .
C53 C 0.62845(15) 0.21418(14) 0.87440(11) 0.0292(4) Uani 1 1 d . . . . .
H53A H 0.607696 0.177743 0.930846 0.035 Uiso 1 1 calc R U . . .
H53B H 0.709946 0.205094 0.873355 0.035 Uiso 1 1 calc R U . . .
C54 C 0.59207(16) 0.32028(14) 0.85454(12) 0.0337(5) Uani 1 1 d . . . . .
H54A H 0.511079 0.330442 0.858491 0.040 Uiso 1 1 calc R U . . .
H54B H 0.611060 0.358075 0.797957 0.040 Uiso 1 1 calc R U . . .
C55 C 0.65048(17) 0.35342(14) 0.91521(12) 0.0355(5) Uani 1 1 d . . . . .
H55A H 0.630982 0.314718 0.971424 0.043 Uiso 1 1 calc R U . . .
H55B H 0.731281 0.341058 0.911629 0.043 Uiso 1 1 calc R U . . .
C56 C 0.62119(17) 0.45947(14) 0.90054(12) 0.0363(5) Uani 1 1 d . . . . .
H56A H 0.540066 0.472741 0.901352 0.044 Uiso 1 1 calc R U . . .
H56B H 0.644399 0.498424 0.845482 0.044 Uiso 1 1 calc R U . . .
C57 C 0.67579(17) 0.49012(14) 0.96449(12) 0.0364(5) Uani 1 1 d . . . . .
H57A H 0.651807 0.451452 1.019387 0.044 Uiso 1 1 calc R U . . .
H57B H 0.756815 0.475694 0.964180 0.044 Uiso 1 1 calc R U . . .
C58 C 0.64912(19) 0.59603(15) 0.95061(13) 0.0431(6) Uani 1 1 d . . . . .
H58A H 0.568197 0.612770 0.942389 0.052 Uiso 1 1 calc R U . . .
H58B H 0.683138 0.634359 0.899612 0.052 Uiso 1 1 calc R U . . .
C59 C 0.68908(19) 0.62435(16) 1.02101(14) 0.0443(6) Uani 1 1 d . . . . .
H59A H 0.664265 0.692379 1.007661 0.053 Uiso 1 1 calc R U . . .
H59B H 0.653709 0.587417 1.071846 0.053 Uiso 1 1 calc R U . . .
C60 C 0.8145(2) 0.6077(2) 1.03669(19) 0.0708(8) Uani 1 1 d . . . . .
H60A H 0.833664 0.627028 1.081554 0.085 Uiso 1 1 calc R U . . .
H60B H 0.839725 0.540262 1.051404 0.085 Uiso 1 1 calc R U . . .
H60C H 0.850292 0.645328 0.987155 0.085 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2016/4 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.153(2) . ?
N2 C2 1.152(2) . ?
N3 C10 1.151(2) . ?
N4 C11 1.150(2) . ?
N5 C13 1.154(2) . ?
N6 C14 1.156(2) . ?
N7 C22 1.154(2) . ?
N8 C23 1.151(2) . ?
N9 C26 1.490(2) . ?
N9 C25 1.499(2) . ?
N9 C27 1.514(2) . ?
N9 C35 1.519(2) . ?
N10 C44 1.490(2) . ?
N10 C43 1.507(2) . ?
N10 C53 1.515(2) . ?
N10 C45 1.520(2) . ?
C1 C3 1.422(2) . ?
C2 C3 1.423(3) . ?
C3 C4 1.416(2) . ?
C4 C7 1.418(2) . ?
C4 C5 1.419(2) . ?
C5 C6 1.363(2) . ?
C5 H5 0.9300 . ?
C6 C9 1.423(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.361(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.416(2) . ?
C8 H8 0.9300 . ?
C9 C12 1.415(2) . ?
C10 C12 1.413(3) . ?
C11 C12 1.422(3) . ?
C13 C15 1.427(2) . ?
C14 C15 1.419(3) . ?
C15 C16 1.418(2) . ?
C16 C17 1.408(2) . ?
C16 C19 1.424(2) . ?
C17 C18 1.365(3) . ?
C17 H17 0.9300 . ?
C18 C21 1.421(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.359(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.419(2) . ?
C20 H20 0.9300 . ?
C21 C24 1.413(3) . ?
C22 C24 1.416(3) . ?
C23 C24 1.421(3) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C28 1.514(3) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C29 1.520(2) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 C30 1.514(3) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.518(2) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C32 1.517(3) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.519(3) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C34 1.511(3) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 C36 1.509(3) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 C37 1.532(3) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 C38 1.519(3) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 C39 1.512(3) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 C40 1.524(3) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C40 C41 1.512(3) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C41 C42 1.512(4) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
C45 C46 1.518(3) . ?
C45 H45A 0.9700 . ?
C45 H45B 0.9700 . ?
C46 C47 1.525(2) . ?
C46 H46A 0.9700 . ?
C46 H46B 0.9700 . ?
C47 C48 1.521(3) . ?
C47 H47A 0.9700 . ?
C47 H47B 0.9700 . ?
C48 C49 1.518(3) . ?
C48 H48A 0.9700 . ?
C48 H48B 0.9700 . ?
C49 C50 1.525(3) . ?
C49 H49A 0.9700 . ?
C49 H49B 0.9700 . ?
C50 C51 1.525(3) . ?
C50 H50A 0.9700 . ?
C50 H50B 0.9700 . ?
C51 C52 1.513(4) . ?
C51 H51A 0.9700 . ?
C51 H51B 0.9700 . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 0.9600 . ?
C53 C54 1.510(3) . ?
C53 H53A 0.9700 . ?
C53 H53B 0.9700 . ?
C54 C55 1.517(3) . ?
C54 H54A 0.9700 . ?
C54 H54B 0.9700 . ?
C55 C56 1.514(3) . ?
C55 H55A 0.9700 . ?
C55 H55B 0.9700 . ?
C56 C57 1.519(3) . ?
C56 H56A 0.9700 . ?
C56 H56B 0.9700 . ?
C57 C58 1.512(3) . ?
C57 H57A 0.9700 . ?
C57 H57B 0.9700 . ?
C58 C59 1.525(3) . ?
C58 H58A 0.9700 . ?
C58 H58B 0.9700 . ?
C59 C60 1.501(3) . ?
C59 H59A 0.9700 . ?
C59 H59B 0.9700 . ?
C60 H60A 0.9600 . ?
C60 H60B 0.9600 . ?
C60 H60C 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
C26 N9 C25 108.30(14) . . ?
C26 N9 C27 108.54(13) . . ?
C25 N9 C27 109.95(14) . . ?
C26 N9 C35 110.29(14) . . ?
C25 N9 C35 106.63(13) . . ?
C27 N9 C35 113.02(13) . . ?
C44 N10 C43 108.18(14) . . ?
C44 N10 C53 108.27(13) . . ?
C43 N10 C53 109.82(14) . . ?
C44 N10 C45 110.03(13) . . ?
C43 N10 C45 108.11(12) . . ?
C53 N10 C45 112.35(13) . . ?
N1 C1 C3 178.2(2) . . ?
N2 C2 C3 178.9(2) . . ?
C4 C3 C1 122.48(16) . . ?
C4 C3 C2 122.12(15) . . ?
C1 C3 C2 115.26(16) . . ?
C3 C4 C7 120.94(16) . . ?
C3 C4 C5 121.96(15) . . ?
C7 C4 C5 117.09(16) . . ?
C6 C5 C4 121.44(15) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C9 121.29(16) . . ?
C5 C6 H6 119.4 . . ?
C9 C6 H6 119.4 . . ?
C8 C7 C4 121.48(16) . . ?
C8 C7 H7 119.3 . . ?
C4 C7 H7 119.3 . . ?
C7 C8 C9 121.57(15) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C12 C9 C8 121.17(15) . . ?
C12 C9 C6 121.74(16) . . ?
C8 C9 C6 117.08(15) . . ?
N3 C10 C12 179.7(2) . . ?
N4 C11 C12 178.3(2) . . ?
C10 C12 C9 121.27(16) . . ?
C10 C12 C11 115.90(16) . . ?
C9 C12 C11 122.63(16) . . ?
N5 C13 C15 179.4(2) . . ?
N6 C14 C15 176.9(2) . . ?
C16 C15 C14 120.60(15) . . ?
C16 C15 C13 121.49(16) . . ?
C14 C15 C13 117.35(16) . . ?
C17 C16 C15 121.51(15) . . ?
C17 C16 C19 117.15(16) . . ?
C15 C16 C19 121.32(16) . . ?
C18 C17 C16 121.68(16) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C21 121.22(17) . . ?
C17 C18 H18 119.4 . . ?
C21 C18 H18 119.4 . . ?
C20 C19 C16 121.38(17) . . ?
C20 C19 H19 119.3 . . ?
C16 C19 H19 119.3 . . ?
C19 C20 C21 121.44(16) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
C24 C21 C20 121.75(15) . . ?
C24 C21 C18 121.15(16) . . ?
C20 C21 C18 117.10(16) . . ?
N7 C22 C24 179.1(2) . . ?
N8 C23 C24 179.6(2) . . ?
C21 C24 C22 121.98(15) . . ?
C21 C24 C23 121.55(17) . . ?
C22 C24 C23 116.35(16) . . ?
N9 C25 H25A 109.5 . . ?
N9 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N9 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N9 C26 H26A 109.5 . . ?
N9 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N9 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N9 C27 C28 116.05(13) . . ?
N9 C27 H27A 108.3 . . ?
C28 C27 H27A 108.3 . . ?
N9 C27 H27B 108.3 . . ?
C28 C27 H27B 108.3 . . ?
H27A C27 H27B 107.4 . . ?
C27 C28 C29 110.47(14) . . ?
C27 C28 H28A 109.6 . . ?
C29 C28 H28A 109.6 . . ?
C27 C28 H28B 109.6 . . ?
C29 C28 H28B 109.6 . . ?
H28A C28 H28B 108.1 . . ?
C30 C29 C28 113.89(15) . . ?
C30 C29 H29A 108.8 . . ?
C28 C29 H29A 108.8 . . ?
C30 C29 H29B 108.8 . . ?
C28 C29 H29B 108.8 . . ?
H29A C29 H29B 107.7 . . ?
C29 C30 C31 113.37(15) . . ?
C29 C30 H30A 108.9 . . ?
C31 C30 H30A 108.9 . . ?
C29 C30 H30B 108.9 . . ?
C31 C30 H30B 108.9 . . ?
H30A C30 H30B 107.7 . . ?
C32 C31 C30 114.17(15) . . ?
C32 C31 H31A 108.7 . . ?
C30 C31 H31A 108.7 . . ?
C32 C31 H31B 108.7 . . ?
C30 C31 H31B 108.7 . . ?
H31A C31 H31B 107.6 . . ?
C31 C32 C33 114.55(16) . . ?
C31 C32 H32A 108.6 . . ?
C33 C32 H32A 108.6 . . ?
C31 C32 H32B 108.6 . . ?
C33 C32 H32B 108.6 . . ?
H32A C32 H32B 107.6 . . ?
C34 C33 C32 113.34(18) . . ?
C34 C33 H33A 108.9 . . ?
C32 C33 H33A 108.9 . . ?
C34 C33 H33B 108.9 . . ?
C32 C33 H33B 108.9 . . ?
H33A C33 H33B 107.7 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C36 C35 N9 117.41(14) . . ?
C36 C35 H35A 107.9 . . ?
N9 C35 H35A 107.9 . . ?
C36 C35 H35B 107.9 . . ?
N9 C35 H35B 107.9 . . ?
H35A C35 H35B 107.2 . . ?
C35 C36 C37 108.28(15) . . ?
C35 C36 H36A 110.0 . . ?
C37 C36 H36A 110.0 . . ?
C35 C36 H36B 110.0 . . ?
C37 C36 H36B 110.0 . . ?
H36A C36 H36B 108.4 . . ?
C38 C37 C36 114.68(17) . . ?
C38 C37 H37A 108.6 . . ?
C36 C37 H37A 108.6 . . ?
C38 C37 H37B 108.6 . . ?
C36 C37 H37B 108.6 . . ?
H37A C37 H37B 107.6 . . ?
C39 C38 C37 115.28(18) . . ?
C39 C38 H38A 108.5 . . ?
C37 C38 H38A 108.5 . . ?
C39 C38 H38B 108.5 . . ?
C37 C38 H38B 108.5 . . ?
H38A C38 H38B 107.5 . . ?
C38 C39 C40 115.48(18) . . ?
C38 C39 H39A 108.4 . . ?
C40 C39 H39A 108.4 . . ?
C38 C39 H39B 108.4 . . ?
C40 C39 H39B 108.4 . . ?
H39A C39 H39B 107.5 . . ?
C41 C40 C39 112.88(18) . . ?
C41 C40 H40A 109.0 . . ?
C39 C40 H40A 109.0 . . ?
C41 C40 H40B 109.0 . . ?
C39 C40 H40B 109.0 . . ?
H40A C40 H40B 107.8 . . ?
C40 C41 C42 115.1(2) . . ?
C40 C41 H41A 108.5 . . ?
C42 C41 H41A 108.5 . . ?
C40 C41 H41B 108.5 . . ?
C42 C41 H41B 108.5 . . ?
H41A C41 H41B 107.5 . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
N10 C43 H43A 109.5 . . ?
N10 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
N10 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
N10 C44 H44A 109.5 . . ?
N10 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
N10 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C46 C45 N10 115.01(13) . . ?
C46 C45 H45A 108.5 . . ?
N10 C45 H45A 108.5 . . ?
C46 C45 H45B 108.5 . . ?
N10 C45 H45B 108.5 . . ?
H45A C45 H45B 107.5 . . ?
C45 C46 C47 111.19(14) . . ?
C45 C46 H46A 109.4 . . ?
C47 C46 H46A 109.4 . . ?
C45 C46 H46B 109.4 . . ?
C47 C46 H46B 109.4 . . ?
H46A C46 H46B 108.0 . . ?
C48 C47 C46 111.80(14) . . ?
C48 C47 H47A 109.3 . . ?
C46 C47 H47A 109.3 . . ?
C48 C47 H47B 109.3 . . ?
C46 C47 H47B 109.3 . . ?
H47A C47 H47B 107.9 . . ?
C49 C48 C47 115.00(15) . . ?
C49 C48 H48A 108.5 . . ?
C47 C48 H48A 108.5 . . ?
C49 C48 H48B 108.5 . . ?
C47 C48 H48B 108.5 . . ?
H48A C48 H48B 107.5 . . ?
C48 C49 C50 112.60(16) . . ?
C48 C49 H49A 109.1 . . ?
C50 C49 H49A 109.1 . . ?
C48 C49 H49B 109.1 . . ?
C50 C49 H49B 109.1 . . ?
H49A C49 H49B 107.8 . . ?
C49 C50 C51 115.12(18) . . ?
C49 C50 H50A 108.5 . . ?
C51 C50 H50A 108.5 . . ?
C49 C50 H50B 108.5 . . ?
C51 C50 H50B 108.5 . . ?
H50A C50 H50B 107.5 . . ?
C52 C51 C50 112.9(2) . . ?
C52 C51 H51A 109.0 . . ?
C50 C51 H51A 109.0 . . ?
C52 C51 H51B 109.0 . . ?
C50 C51 H51B 109.0 . . ?
H51A C51 H51B 107.8 . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C54 C53 N10 116.04(14) . . ?
C54 C53 H53A 108.3 . . ?
N10 C53 H53A 108.3 . . ?
C54 C53 H53B 108.3 . . ?
N10 C53 H53B 108.3 . . ?
H53A C53 H53B 107.4 . . ?
C53 C54 C55 109.91(15) . . ?
C53 C54 H54A 109.7 . . ?
C55 C54 H54A 109.7 . . ?
C53 C54 H54B 109.7 . . ?
C55 C54 H54B 109.7 . . ?
H54A C54 H54B 108.2 . . ?
C56 C55 C54 114.54(15) . . ?
C56 C55 H55A 108.6 . . ?
C54 C55 H55A 108.6 . . ?
C56 C55 H55B 108.6 . . ?
C54 C55 H55B 108.6 . . ?
H55A C55 H55B 107.6 . . ?
C55 C56 C57 113.78(15) . . ?
C55 C56 H56A 108.8 . . ?
C57 C56 H56A 108.8 . . ?
C55 C56 H56B 108.8 . . ?
C57 C56 H56B 108.8 . . ?
H56A C56 H56B 107.7 . . ?
C58 C57 C56 114.85(16) . . ?
C58 C57 H57A 108.6 . . ?
C56 C57 H57A 108.6 . . ?
C58 C57 H57B 108.6 . . ?
C56 C57 H57B 108.6 . . ?
H57A C57 H57B 107.5 . . ?
C57 C58 C59 115.17(16) . . ?
C57 C58 H58A 108.5 . . ?
C59 C58 H58A 108.5 . . ?
C57 C58 H58B 108.5 . . ?
C59 C58 H58B 108.5 . . ?
H58A C58 H58B 107.5 . . ?
C60 C59 C58 113.9(2) . . ?
C60 C59 H59A 108.8 . . ?
C58 C59 H59A 108.8 . . ?
C60 C59 H59B 108.8 . . ?
C58 C59 H59B 108.8 . . ?
H59A C59 H59B 107.7 . . ?
C59 C60 H60A 109.5 . . ?
C59 C60 H60B 109.5 . . ?
H60A C60 H60B 109.5 . . ?
C59 C60 H60C 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 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
C1 C3 C4 C7 179.50(17) . . . . ?
C2 C3 C4 C7 -4.9(3) . . . . ?
C1 C3 C4 C5 -0.9(3) . . . . ?
C2 C3 C4 C5 174.70(17) . . . . ?
C3 C4 C5 C6 178.34(17) . . . . ?
C7 C4 C5 C6 -2.1(3) . . . . ?
C4 C5 C6 C9 0.4(3) . . . . ?
C3 C4 C7 C8 -178.53(17) . . . . ?
C5 C4 C7 C8 1.9(3) . . . . ?
C4 C7 C8 C9 0.0(3) . . . . ?
C7 C8 C9 C12 179.31(17) . . . . ?
C7 C8 C9 C6 -1.6(3) . . . . ?
C5 C6 C9 C12 -179.51(17) . . . . ?
C5 C6 C9 C8 1.4(3) . . . . ?
C8 C9 C12 C10 -176.87(18) . . . . ?
C6 C9 C12 C10 4.1(3) . . . . ?
C8 C9 C12 C11 8.6(3) . . . . ?
C6 C9 C12 C11 -170.46(18) . . . . ?
C14 C15 C16 C17 -176.26(17) . . . . ?
C13 C15 C16 C17 -5.0(3) . . . . ?
C14 C15 C16 C19 2.2(3) . . . . ?
C13 C15 C16 C19 173.44(17) . . . . ?
C15 C16 C17 C18 -179.62(18) . . . . ?
C19 C16 C17 C18 1.8(3) . . . . ?
C16 C17 C18 C21 -0.4(3) . . . . ?
C17 C16 C19 C20 -1.4(3) . . . . ?
C15 C16 C19 C20 -179.94(17) . . . . ?
C16 C19 C20 C21 -0.4(3) . . . . ?
C19 C20 C21 C24 -178.80(18) . . . . ?
C19 C20 C21 C18 1.9(3) . . . . ?
C17 C18 C21 C24 179.23(17) . . . . ?
C17 C18 C21 C20 -1.4(3) . . . . ?
C20 C21 C24 C22 -174.12(18) . . . . ?
C18 C21 C24 C22 5.2(3) . . . . ?
C20 C21 C24 C23 1.7(3) . . . . ?
C18 C21 C24 C23 -179.00(18) . . . . ?
C26 N9 C27 C28 168.86(15) . . . . ?
C25 N9 C27 C28 50.6(2) . . . . ?
C35 N9 C27 C28 -68.46(19) . . . . ?
N9 C27 C28 C29 169.39(15) . . . . ?
C27 C28 C29 C30 177.30(16) . . . . ?
C28 C29 C30 C31 175.15(17) . . . . ?
C29 C30 C31 C32 177.90(17) . . . . ?
C30 C31 C32 C33 175.11(18) . . . . ?
C31 C32 C33 C34 64.0(3) . . . . ?
C26 N9 C35 C36 54.1(2) . . . . ?
C25 N9 C35 C36 171.45(16) . . . . ?
C27 N9 C35 C36 -67.6(2) . . . . ?
N9 C35 C36 C37 179.95(15) . . . . ?
C35 C36 C37 C38 178.64(18) . . . . ?
C36 C37 C38 C39 -66.5(2) . . . . ?
C37 C38 C39 C40 -62.0(3) . . . . ?
C38 C39 C40 C41 -174.06(19) . . . . ?
C39 C40 C41 C42 -175.9(2) . . . . ?
C44 N10 C45 C46 59.01(19) . . . . ?
C43 N10 C45 C46 176.95(15) . . . . ?
C53 N10 C45 C46 -61.70(19) . . . . ?
N10 C45 C46 C47 170.66(15) . . . . ?
C45 C46 C47 C48 177.37(16) . . . . ?
C46 C47 C48 C49 176.41(17) . . . . ?
C47 C48 C49 C50 -179.07(17) . . . . ?
C48 C49 C50 C51 171.1(2) . . . . ?
C49 C50 C51 C52 -72.5(3) . . . . ?
C44 N10 C53 C54 -177.78(16) . . . . ?
C43 N10 C53 C54 64.3(2) . . . . ?
C45 N10 C53 C54 -56.1(2) . . . . ?
N10 C53 C54 C55 -177.91(16) . . . . ?
C53 C54 C55 C56 179.35(17) . . . . ?
C54 C55 C56 C57 177.06(18) . . . . ?
C55 C56 C57 C58 179.23(18) . . . . ?
C56 C57 C58 C59 171.43(19) . . . . ?
C57 C58 C59 C60 61.8(3) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
