# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_BI2C_RT
_database_code_depnum_ccdc_archive 'CCDC 1989814'
loop_
_audit_author_name
_audit_author_address
'Sachio Horiuchi'
;National Institute of Advanced Science and Technology 
Japan
;
_audit_update_record             
;
2020-03-11 deposited with the CCDC.	2020-05-13 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C15 H12 N4'
_chemical_formula_moiety         'C15 H12 N4'
_chemical_formula_weight         248.29
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   18.3346(7)
_cell_length_b                   15.7546(3)
_cell_length_c                   18.3241(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.5310(10)
_cell_angle_gamma                90.0000
_cell_volume                     5292.8(2)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    18146
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      55.07
_cell_measurement_temperature    293
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2080.00
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku, ????)'
_exptl_absorpt_correction_T_min  0.868
_exptl_absorpt_correction_T_max  1.000

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

_diffrn_ambient_temperature      293
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     1.000
_diffrn_measurement_device_type  'IP DSC (Rigaku)'
_diffrn_reflns_number            24825
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_theta_max         46.062
_diffrn_reflns_theta_min         2.398
_diffrn_reflns_theta_full        36.870
_diffrn_measured_fraction_theta_max 0.557
_diffrn_measured_fraction_theta_full 0.658
_diffrn_reflns_Laue_measured_fraction_max 0.557
_diffrn_reflns_Laue_measured_fraction_full 0.658
_diffrn_reflns_point_group_measured_fraction_max 0.557
_diffrn_reflns_point_group_measured_fraction_full 0.658
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             9236
_reflns_number_gt                4766
_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          0.0797
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1324
_refine_ls_wR_factor_gt          0.1173
_refine_ls_number_restraints     9
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         9236
_refine_ls_number_parameters     718
_refine_ls_goodness_of_fit_ref   0.909
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0802P)²] 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          0.001
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.13
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00075(11)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0074 0.0035
;
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 0.0135 0.0070
;
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 0.92466(8) -0.11770(7) -0.08118(7) 0.0554(4) Uani 1 1 d . . . . .
H41 H 0.9753(10) -0.1024(10) -0.0797(9) 0.084(6) Uiso 1 1 d . . . . .
N2 N 0.80553(7) -0.09616(8) -0.07510(8) 0.0743(5) Uani 1 1 d . . . . .
N3 N 0.92942(7) 0.06839(7) 0.08588(8) 0.0575(4) Uani 1 1 d . . . . .
N4 N 0.82494(9) -0.00262(8) 0.08655(8) 0.0565(5) Uani 1 1 d . . . . .
H42 H 0.7853(10) -0.0296(10) 0.0717(9) 0.075(5) Uiso 1 1 d . . . . .
N5 N 0.66167(8) 0.18412(7) 0.17378(7) 0.0568(5) Uani 1 1 d . . . . .
N6 N 0.65894(9) 0.25171(7) 0.06697(7) 0.0552(5) Uani 1 1 d . . . . .
H43 H 0.6765(9) 0.2864(10) 0.0218(10) 0.088(6) Uiso 1 1 d . . . . .
N7 N 0.83085(7) 0.36277(7) 0.16970(6) 0.0595(4) Uani 1 1 d . . . . .
N8 N 0.82242(9) 0.35182(8) 0.04974(7) 0.0697(5) Uani 1 1 d . . . . .
H44 H 0.8225(11) 0.3162(12) -0.0002(11) 0.128(7) Uiso 1 1 d . . . . .
N9 N 0.69499(8) -0.09740(8) 0.06916(8) 0.0737(5) Uani 1 1 d . . . . .
N10 N 0.57570(8) -0.11620(7) 0.08157(7) 0.0567(5) Uani 1 1 d . . . . .
H45 H 0.5228(10) -0.1012(10) 0.0812(9) 0.085(6) Uiso 1 1 d . . . . .
N11 N 0.67537(9) -0.00271(8) -0.09054(8) 0.0582(5) Uani 1 1 d . . . . .
H46 H 0.7153(10) -0.0293(10) -0.0748(9) 0.076(5) Uiso 1 1 d . . . . .
N12 N 0.57011(7) 0.06704(7) -0.08956(8) 0.0570(5) Uani 1 1 d . . . . .
N13 N 0.68024(8) 0.34516(8) -0.06103(7) 0.0695(5) Uani 1 1 d . . . . .
N14 N 0.66872(7) 0.36505(7) -0.17990(6) 0.0568(4) Uani 1 1 d . . . . .
H47 H 0.6692(9) 0.3495(9) -0.2329(9) 0.089(5) Uiso 1 1 d . . . . .
N15 N 0.83737(8) 0.24678(7) -0.07585(7) 0.0583(5) Uani 1 1 d . . . . .
N16 N 0.84333(8) 0.18610(7) -0.18543(7) 0.0573(5) Uani 1 1 d . . . . .
H48 H 0.8347(10) 0.1667(10) -0.2377(9) 0.097(6) Uiso 1 1 d . . . . .
C1 C 0.87026(9) -0.06375(8) -0.06448(8) 0.0519(5) Uani 1 1 d . . . . .
C2 C 0.89265(9) -0.19209(8) -0.10475(8) 0.0537(5) Uani 1 1 d . . . . .
C3 C 0.92214(10) -0.26831(10) -0.12861(10) 0.0769(6) Uani 1 1 d . . . . .
H3 H 0.972257 -0.276583 -0.131392 0.092 Uiso 1 1 calc R U . . .
C4 C 0.87345(13) -0.33079(11) -0.14787(12) 0.0942(8) Uani 1 1 d . . . . .
H4 H 0.890921 -0.382835 -0.164068 0.113 Uiso 1 1 calc R U . . .
C5 C 0.79999(14) -0.31817(13) -0.14376(15) 0.1166(9) Uani 1 1 d . . . . .
H5 H 0.768767 -0.361974 -0.157536 0.140 Uiso 1 1 calc R U . . .
C6 C 0.77030(11) -0.24251(13) -0.11981(14) 0.1134(9) Uani 1 1 d . . . . .
H6 H 0.720133 -0.234887 -0.116650 0.136 Uiso 1 1 calc R U . . .
C7 C 0.81906(10) -0.17828(10) -0.10065(10) 0.0689(6) Uani 1 1 d . . . . .
C8 C 0.88422(9) 0.02334(8) -0.03489(8) 0.0609(5) Uani 1 1 d . . . . .
H8A H 0.932070 0.041884 -0.050435 0.073 Uiso 1 1 calc R U . . .
H8B H 0.848548 0.062072 -0.055714 0.073 Uiso 1 1 calc R U . . .
C9 C 0.88082(10) 0.02873(8) 0.04598(9) 0.0507(5) Uani 1 1 d . . . . .
C10 C 0.90343(10) 0.06266(8) 0.15735(10) 0.0551(5) Uani 1 1 d . . . . .
C11 C 0.93216(12) 0.09526(10) 0.22178(12) 0.0745(7) Uani 1 1 d . . . . .
H11 H 0.976087 0.124781 0.222290 0.089 Uiso 1 1 calc R U . . .
C12 C 0.89346(14) 0.08248(11) 0.28516(13) 0.0814(8) Uani 1 1 d . . . . .
H12 H 0.911785 0.104183 0.328827 0.098 Uiso 1 1 calc R U . . .
C13 C 0.82785(12) 0.03807(11) 0.28557(11) 0.0816(7) Uani 1 1 d . . . . .
H13 H 0.803353 0.030677 0.329326 0.098 Uiso 1 1 calc R U . . .
C14 C 0.79866(11) 0.00494(10) 0.22234(11) 0.0712(7) Uani 1 1 d . . . . .
H14 H 0.754868 -0.024851 0.222100 0.085 Uiso 1 1 calc R U . . .
C15 C 0.83791(10) 0.01822(8) 0.15867(10) 0.0551(6) Uani 1 1 d . . . . .
C16 C 0.70035(10) 0.22140(8) 0.12262(8) 0.0506(5) Uani 1 1 d . . . . .
C17 C 0.58954(11) 0.18982(8) 0.15132(8) 0.0555(6) Uani 1 1 d . . . . .
C18 C 0.52609(12) 0.15921(10) 0.18319(10) 0.0749(7) Uani 1 1 d . . . . .
H18 H 0.527647 0.131395 0.227945 0.090 Uiso 1 1 calc R U . . .
C19 C 0.46139(11) 0.17119(11) 0.14682(11) 0.0827(7) Uani 1 1 d . . . . .
H19 H 0.418201 0.151453 0.166918 0.099 Uiso 1 1 calc R U . . .
C20 C 0.46003(13) 0.21298(11) 0.07962(12) 0.0788(7) Uani 1 1 d . . . . .
H20 H 0.415501 0.220204 0.055708 0.095 Uiso 1 1 calc R U . . .
C21 C 0.52232(11) 0.24393(10) 0.04742(10) 0.0694(7) Uani 1 1 d . . . . .
H21 H 0.520519 0.271756 0.002678 0.083 Uiso 1 1 calc R U . . .
C22 C 0.58757(10) 0.23184(8) 0.08445(8) 0.0518(5) Uani 1 1 d . . . . .
C23 C 0.78161(9) 0.22665(8) 0.12195(8) 0.0598(5) Uani 1 1 d . . . . .
H23A H 0.799285 0.192351 0.081859 0.072 Uiso 1 1 calc R U . . .
H23B H 0.800324 0.201890 0.166828 0.072 Uiso 1 1 calc R U . . .
C24 C 0.81238(9) 0.31403(8) 0.11460(8) 0.0516(5) Uani 1 1 d . . . . .
C25 C 0.85601(9) 0.43744(9) 0.13797(8) 0.0588(5) Uani 1 1 d . . . . .
C26 C 0.88347(11) 0.51138(10) 0.16979(9) 0.0835(7) Uani 1 1 d . . . . .
H26 H 0.887496 0.516527 0.220227 0.100 Uiso 1 1 calc R U . . .
C27 C 0.90431(13) 0.57605(11) 0.12492(11) 0.0995(8) Uani 1 1 d . . . . .
H27 H 0.923491 0.625359 0.145341 0.119 Uiso 1 1 calc R U . . .
C28 C 0.89765(15) 0.57006(12) 0.05062(12) 0.1235(10) Uani 1 1 d . . . . .
H28 H 0.911407 0.615806 0.021779 0.148 Uiso 1 1 calc R U . . .
C29 C 0.87109(14) 0.49792(13) 0.01780(10) 0.1136(10) Uani 1 1 d . . . . .
H29 H 0.866931 0.493538 -0.032679 0.136 Uiso 1 1 calc R U . . .
C30 C 0.85084(10) 0.43217(9) 0.06313(8) 0.0692(6) Uani 1 1 d . . . . .
C31 C 0.63012(9) -0.06395(8) 0.06127(8) 0.0532(5) Uani 1 1 d . . . . .
C32 C 0.68155(10) -0.17872(10) 0.09671(10) 0.0706(6) Uani 1 1 d . . . . .
C33 C 0.73032(11) -0.24361(13) 0.11443(14) 0.1140(9) Uani 1 1 d . . . . .
H33 H 0.780367 -0.237092 0.108837 0.137 Uiso 1 1 calc R U . . .
C34 C 0.70066(14) -0.31799(13) 0.14066(16) 0.1235(10) Uani 1 1 d . . . . .
H34 H 0.731837 -0.362293 0.153268 0.148 Uiso 1 1 calc R U . . .
C35 C 0.62711(14) -0.32910(11) 0.14886(13) 0.1017(8) Uani 1 1 d . . . . .
H35 H 0.609838 -0.380468 0.166777 0.122 Uiso 1 1 calc R U . . .
C36 C 0.57813(11) -0.26586(10) 0.13115(10) 0.0830(7) Uani 1 1 d . . . . .
H36 H 0.528125 -0.272931 0.136674 0.100 Uiso 1 1 calc R U . . .
C37 C 0.60774(10) -0.19097(9) 0.10459(9) 0.0566(5) Uani 1 1 d . . . . .
C38 C 0.61640(9) 0.02292(8) 0.03105(8) 0.0625(6) Uani 1 1 d . . . . .
H38A H 0.568649 0.041769 0.046623 0.075 Uiso 1 1 calc R U . . .
H38B H 0.652210 0.061631 0.051648 0.075 Uiso 1 1 calc R U . . .
C39 C 0.61959(10) 0.02822(8) -0.04995(9) 0.0528(6) Uani 1 1 d . . . . .
C40 C 0.66234(10) 0.01806(8) -0.16285(10) 0.0568(6) Uani 1 1 d . . . . .
C41 C 0.70135(12) 0.00562(10) -0.22654(11) 0.0740(7) Uani 1 1 d . . . . .
H41A H 0.745454 -0.023525 -0.226639 0.089 Uiso 1 1 calc R U . . .
C42 C 0.67142(13) 0.03858(11) -0.28935(11) 0.0850(7) Uani 1 1 d . . . . .
H42A H 0.695939 0.031907 -0.333186 0.102 Uiso 1 1 calc R U . . .
C43 C 0.60538(14) 0.08164(11) -0.28892(13) 0.0846(8) Uani 1 1 d . . . . .
H43A H 0.586688 0.102966 -0.332564 0.101 Uiso 1 1 calc R U . . .
C44 C 0.56673(12) 0.09366(10) -0.22557(12) 0.0762(7) Uani 1 1 d . . . . .
H44A H 0.522434 0.122426 -0.225989 0.091 Uiso 1 1 calc R U . . .
C45 C 0.59603(10) 0.06146(8) -0.16106(10) 0.0551(6) Uani 1 1 d . . . . .
C46 C 0.68931(9) 0.31225(8) -0.12610(8) 0.0530(5) Uani 1 1 d . . . . .
C47 C 0.65174(10) 0.42653(10) -0.07317(8) 0.0675(6) Uani 1 1 d . . . . .
C48 C 0.63258(13) 0.49054(13) -0.02487(10) 0.1033(9) Uani 1 1 d . . . . .
H48A H 0.637541 0.483101 0.025274 0.124 Uiso 1 1 calc R U . . .
C49 C 0.60607(14) 0.56517(13) -0.05341(12) 0.1191(10) Uani 1 1 d . . . . .
H49 H 0.593655 0.609240 -0.022132 0.143 Uiso 1 1 calc R U . . .
C50 C 0.59762(13) 0.57572(11) -0.12737(11) 0.1015(8) Uani 1 1 d . . . . .
H50 H 0.578378 0.626452 -0.144953 0.122 Uiso 1 1 calc R U . . .
C51 C 0.61663(11) 0.51393(10) -0.17593(9) 0.0820(7) Uani 1 1 d . . . . .
H51 H 0.611426 0.521994 -0.225982 0.098 Uiso 1 1 calc R U . . .
C52 C 0.64402(9) 0.43864(9) -0.14750(8) 0.0580(5) Uani 1 1 d . . . . .
C53 C 0.71963(8) 0.22611(8) -0.14088(8) 0.0592(5) Uani 1 1 d . . . . .
H53A H 0.698014 0.185970 -0.107262 0.071 Uiso 1 1 calc R U . . .
H53B H 0.705674 0.209190 -0.189952 0.071 Uiso 1 1 calc R U . . .
C54 C 0.80059(10) 0.22127(8) -0.13363(8) 0.0511(5) Uani 1 1 d . . . . .
C55 C 0.90972(10) 0.22693(8) -0.09229(8) 0.0538(6) Uani 1 1 d . . . . .
C56 C 0.97336(12) 0.23729(10) -0.05142(10) 0.0706(7) Uani 1 1 d . . . . .
H56 H 0.972362 0.262327 -0.005476 0.085 Uiso 1 1 calc R U . . .
C57 C 1.03797(13) 0.20943(11) -0.08088(12) 0.0783(7) Uani 1 1 d . . . . .
H57 H 1.080825 0.216005 -0.053919 0.094 Uiso 1 1 calc R U . . .
C58 C 1.04148(11) 0.17173(10) -0.14965(11) 0.0833(6) Uani 1 1 d . . . . .
H58 H 1.086190 0.153916 -0.167681 0.100 Uiso 1 1 calc R U . . .
C59 C 0.97946(12) 0.16084(11) -0.19070(11) 0.0776(7) Uani 1 1 d . . . . .
H59 H 0.980749 0.135386 -0.236463 0.093 Uiso 1 1 calc R U . . .
C60 C 0.91475(11) 0.18934(8) -0.16116(9) 0.0565(6) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL Version 2018/3 (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 1.3478(19) . ?
N1 C2 1.3783(17) . ?
N1 H41 0.959(18) . ?
N2 C1 1.3048(19) . ?
N2 C7 1.3989(18) . ?
N3 C9 1.3065(16) . ?
N3 C10 1.401(2) . ?
N4 C9 1.364(2) . ?
N4 C15 1.380(2) . ?
N4 H42 0.883(16) . ?
N5 C16 1.319(2) . ?
N5 C17 1.384(2) . ?
N6 C16 1.3529(16) . ?
N6 C22 1.386(2) . ?
N6 H43 1.044(18) . ?
N7 C24 1.3105(16) . ?
N7 C25 1.3927(17) . ?
N8 C24 1.3436(19) . ?
N8 C30 1.3899(18) . ?
N8 H44 1.072(19) . ?
N9 C31 1.3076(19) . ?
N9 C32 1.3997(19) . ?
N10 C31 1.3485(19) . ?
N10 C37 1.3805(17) . ?
N10 H45 0.999(18) . ?
N11 C39 1.360(2) . ?
N11 C40 1.384(2) . ?
N11 H46 0.889(16) . ?
N12 C39 1.3082(17) . ?
N12 C45 1.401(2) . ?
N13 C46 1.3121(18) . ?
N13 C47 1.4014(18) . ?
N14 C46 1.3414(15) . ?
N14 C52 1.3808(18) . ?
N14 H47 1.002(16) . ?
N15 C54 1.3130(16) . ?
N15 C55 1.398(2) . ?
N16 C54 1.355(2) . ?
N16 C60 1.380(2) . ?
N16 H48 1.017(16) . ?
C1 C8 1.4965(17) . ?
C2 C7 1.369(2) . ?
C2 C3 1.389(2) . ?
C3 C4 1.373(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.364(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.393(2) . ?
C6 H6 0.9300 . ?
C8 C9 1.486(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C10 C11 1.387(2) . ?
C10 C15 1.391(2) . ?
C11 C12 1.381(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.392(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.375(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.392(2) . ?
C14 H14 0.9300 . ?
C16 C23 1.492(2) . ?
C17 C18 1.393(2) . ?
C17 C22 1.393(2) . ?
C18 C19 1.368(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.396(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.379(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.383(2) . ?
C21 H21 0.9300 . ?
C23 C24 1.4943(18) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C25 C30 1.376(2) . ?
C25 C26 1.3946(19) . ?
C26 C27 1.366(2) . ?
C26 H26 0.9300 . ?
C27 C28 1.369(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.373(2) . ?
C28 H28 0.9300 . ?
C29 C30 1.381(2) . ?
C29 H29 0.9300 . ?
C31 C38 1.4968(17) . ?
C32 C37 1.376(2) . ?
C32 C33 1.395(2) . ?
C33 C34 1.380(3) . ?
C33 H33 0.9300 . ?
C34 C35 1.369(3) . ?
C34 H34 0.9300 . ?
C35 C36 1.378(2) . ?
C35 H35 0.9300 . ?
C36 C37 1.389(2) . ?
C36 H36 0.9300 . ?
C38 C39 1.488(2) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C40 C41 1.388(2) . ?
C40 C45 1.396(2) . ?
C41 C42 1.372(2) . ?
C41 H41A 0.9300 . ?
C42 C43 1.388(3) . ?
C42 H42A 0.9300 . ?
C43 C44 1.379(3) . ?
C43 H43A 0.9300 . ?
C44 C45 1.390(2) . ?
C44 H44A 0.9300 . ?
C46 C53 1.4924(18) . ?
C47 C52 1.381(2) . ?
C47 C48 1.389(2) . ?
C48 C49 1.374(2) . ?
C48 H48A 0.9300 . ?
C49 C50 1.373(3) . ?
C49 H49 0.9300 . ?
C50 C51 1.366(2) . ?
C50 H50 0.9300 . ?
C51 C52 1.3877(19) . ?
C51 H51 0.9300 . ?
C53 C54 1.491(2) . ?
C53 H53A 0.9700 . ?
C53 H53B 0.9700 . ?
C55 C56 1.390(2) . ?
C55 C60 1.398(2) . ?
C56 C57 1.378(3) . ?
C56 H56 0.9300 . ?
C57 C58 1.395(3) . ?
C57 H57 0.9300 . ?
C58 C59 1.368(2) . ?
C58 H58 0.9300 . ?
C59 C60 1.384(2) . ?
C59 H59 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
C1 N1 C2 107.07(13) . . ?
C1 N1 H41 123.6(10) . . ?
C2 N1 H41 129.2(10) . . ?
C1 N2 C7 104.36(13) . . ?
C9 N3 C10 104.84(14) . . ?
C9 N4 C15 108.18(14) . . ?
C9 N4 H42 128.8(11) . . ?
C15 N4 H42 123.0(11) . . ?
C16 N5 C17 106.18(12) . . ?
C16 N6 C22 105.70(14) . . ?
C16 N6 H43 127.4(9) . . ?
C22 N6 H43 126.8(9) . . ?
C24 N7 C25 104.93(12) . . ?
C24 N8 C30 107.56(12) . . ?
C24 N8 H44 121.6(10) . . ?
C30 N8 H44 128.6(11) . . ?
C31 N9 C32 104.22(14) . . ?
C31 N10 C37 106.94(14) . . ?
C31 N10 H45 125.1(10) . . ?
C37 N10 H45 127.9(10) . . ?
C39 N11 C40 108.35(14) . . ?
C39 N11 H46 127.8(11) . . ?
C40 N11 H46 123.8(11) . . ?
C39 N12 C45 104.49(15) . . ?
C46 N13 C47 105.51(11) . . ?
C46 N14 C52 107.21(12) . . ?
C46 N14 H47 123.8(9) . . ?
C52 N14 H47 128.9(9) . . ?
C54 N15 C55 103.82(14) . . ?
C54 N16 C60 108.20(13) . . ?
C54 N16 H48 134.2(10) . . ?
C60 N16 H48 117.0(10) . . ?
N2 C1 N1 113.16(12) . . ?
N2 C1 C8 124.40(15) . . ?
N1 C1 C8 122.41(14) . . ?
C7 C2 N1 105.35(13) . . ?
C7 C2 C3 122.76(14) . . ?
N1 C2 C3 131.90(16) . . ?
C4 C3 C2 116.53(18) . . ?
C4 C3 H3 121.7 . . ?
C2 C3 H3 121.7 . . ?
C5 C4 C3 121.43(18) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 122.31(18) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C5 C6 C7 116.90(19) . . ?
C5 C6 H6 121.6 . . ?
C7 C6 H6 121.6 . . ?
C2 C7 C6 120.07(16) . . ?
C2 C7 N2 110.07(13) . . ?
C6 C7 N2 129.86(17) . . ?
C9 C8 C1 113.88(12) . . ?
C9 C8 H8A 108.8 . . ?
C1 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
C1 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
N3 C9 N4 112.34(16) . . ?
N3 C9 C8 123.41(18) . . ?
N4 C9 C8 124.15(13) . . ?
C11 C10 C15 119.5(2) . . ?
C11 C10 N3 129.96(18) . . ?
C15 C10 N3 110.49(14) . . ?
C12 C11 C10 117.89(18) . . ?
C12 C11 H11 121.1 . . ?
C10 C11 H11 121.1 . . ?
C11 C12 C13 121.90(18) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C14 C13 C12 121.1(2) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 116.68(18) . . ?
C13 C14 H14 121.7 . . ?
C15 C14 H14 121.7 . . ?
N4 C15 C10 104.14(17) . . ?
N4 C15 C14 132.90(17) . . ?
C10 C15 C14 122.92(16) . . ?
N5 C16 N6 113.03(15) . . ?
N5 C16 C23 125.04(12) . . ?
N6 C16 C23 121.84(16) . . ?
N5 C17 C18 130.72(14) . . ?
N5 C17 C22 108.01(17) . . ?
C18 C17 C22 121.23(16) . . ?
C19 C18 C17 118.15(17) . . ?
C19 C18 H18 120.9 . . ?
C17 C18 H18 120.9 . . ?
C18 C19 C20 120.2(2) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C21 C20 C19 122.40(17) . . ?
C21 C20 H20 118.8 . . ?
C19 C20 H20 118.8 . . ?
C20 C21 C22 117.21(16) . . ?
C20 C21 H21 121.4 . . ?
C22 C21 H21 121.4 . . ?
C21 C22 N6 132.05(16) . . ?
C21 C22 C17 120.82(19) . . ?
N6 C22 C17 107.09(14) . . ?
C16 C23 C24 115.44(12) . . ?
C16 C23 H23A 108.4 . . ?
C24 C23 H23A 108.4 . . ?
C16 C23 H23B 108.4 . . ?
C24 C23 H23B 108.4 . . ?
H23A C23 H23B 107.5 . . ?
N7 C24 N8 112.66(12) . . ?
N7 C24 C23 124.45(13) . . ?
N8 C24 C23 122.88(12) . . ?
C30 C25 N7 110.18(12) . . ?
C30 C25 C26 119.22(14) . . ?
N7 C25 C26 130.60(14) . . ?
C27 C26 C25 118.24(16) . . ?
C27 C26 H26 120.9 . . ?
C25 C26 H26 120.9 . . ?
C26 C27 C28 121.63(16) . . ?
C26 C27 H27 119.2 . . ?
C28 C27 H27 119.2 . . ?
C27 C28 C29 121.38(18) . . ?
C27 C28 H28 119.3 . . ?
C29 C28 H28 119.3 . . ?
C28 C29 C30 116.99(17) . . ?
C28 C29 H29 121.5 . . ?
C30 C29 H29 121.5 . . ?
C25 C30 C29 122.53(15) . . ?
C25 C30 N8 104.66(13) . . ?
C29 C30 N8 132.81(15) . . ?
N9 C31 N10 113.46(13) . . ?
N9 C31 C38 123.98(16) . . ?
N10 C31 C38 122.55(14) . . ?
C37 C32 C33 120.12(16) . . ?
C37 C32 N9 110.05(13) . . ?
C33 C32 N9 129.82(18) . . ?
C34 C33 C32 116.7(2) . . ?
C34 C33 H33 121.6 . . ?
C32 C33 H33 121.6 . . ?
C35 C34 C33 122.57(18) . . ?
C35 C34 H34 118.7 . . ?
C33 C34 H34 118.7 . . ?
C34 C35 C36 121.46(18) . . ?
C34 C35 H35 119.3 . . ?
C36 C35 H35 119.3 . . ?
C35 C36 C37 116.15(19) . . ?
C35 C36 H36 121.9 . . ?
C37 C36 H36 121.9 . . ?
C32 C37 N10 105.33(13) . . ?
C32 C37 C36 122.96(15) . . ?
N10 C37 C36 131.71(17) . . ?
C39 C38 C31 114.35(12) . . ?
C39 C38 H38A 108.7 . . ?
C31 C38 H38A 108.7 . . ?
C39 C38 H38B 108.7 . . ?
C31 C38 H38B 108.7 . . ?
H38A C38 H38B 107.6 . . ?
N12 C39 N11 112.65(16) . . ?
N12 C39 C38 123.10(18) . . ?
N11 C39 C38 124.18(14) . . ?
N11 C40 C41 133.32(17) . . ?
N11 C40 C45 103.66(18) . . ?
C41 C40 C45 123.00(17) . . ?
C42 C41 C40 116.53(19) . . ?
C42 C41 H41A 121.7 . . ?
C40 C41 H41A 121.7 . . ?
C41 C42 C43 121.5(2) . . ?
C41 C42 H42A 119.3 . . ?
C43 C42 H42A 119.3 . . ?
C44 C43 C42 121.82(19) . . ?
C44 C43 H43A 119.1 . . ?
C42 C43 H43A 119.1 . . ?
C43 C44 C45 117.93(19) . . ?
C43 C44 H44A 121.0 . . ?
C45 C44 H44A 121.0 . . ?
C44 C45 C40 119.3(2) . . ?
C44 C45 N12 129.86(18) . . ?
C40 C45 N12 110.85(15) . . ?
N13 C46 N14 112.68(12) . . ?
N13 C46 C53 125.08(12) . . ?
N14 C46 C53 122.23(13) . . ?
C52 C47 C48 120.25(15) . . ?
C52 C47 N13 108.51(13) . . ?
C48 C47 N13 131.23(15) . . ?
C49 C48 C47 118.00(17) . . ?
C49 C48 H48A 121.0 . . ?
C47 C48 H48A 121.0 . . ?
C50 C49 C48 121.05(18) . . ?
C50 C49 H49 119.5 . . ?
C48 C49 H49 119.5 . . ?
C51 C50 C49 121.97(16) . . ?
C51 C50 H50 119.0 . . ?
C49 C50 H50 119.0 . . ?
C50 C51 C52 117.27(15) . . ?
C50 C51 H51 121.4 . . ?
C52 C51 H51 121.4 . . ?
C47 C52 N14 106.08(12) . . ?
C47 C52 C51 121.44(14) . . ?
N14 C52 C51 132.48(14) . . ?
C54 C53 C46 113.74(11) . . ?
C54 C53 H53A 108.8 . . ?
C46 C53 H53A 108.8 . . ?
C54 C53 H53B 108.8 . . ?
C46 C53 H53B 108.8 . . ?
H53A C53 H53B 107.7 . . ?
N15 C54 N16 113.21(15) . . ?
N15 C54 C53 124.03(17) . . ?
N16 C54 C53 122.70(12) . . ?
C56 C55 C60 118.29(19) . . ?
C56 C55 N15 130.59(16) . . ?
C60 C55 N15 111.10(14) . . ?
C57 C56 C55 118.15(17) . . ?
C57 C56 H56 120.9 . . ?
C55 C56 H56 120.9 . . ?
C56 C57 C58 122.44(17) . . ?
C56 C57 H57 118.8 . . ?
C58 C57 H57 118.8 . . ?
C59 C58 C57 120.3(2) . . ?
C59 C58 H58 119.8 . . ?
C57 C58 H58 119.8 . . ?
C58 C59 C60 117.09(18) . . ?
C58 C59 H59 121.5 . . ?
C60 C59 H59 121.5 . . ?
N16 C60 C59 132.57(15) . . ?
N16 C60 C55 103.66(17) . . ?
C59 C60 C55 123.70(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
C7 N2 C1 N1 0.2(2) . . . . ?
C7 N2 C1 C8 -178.19(14) . . . . ?
C2 N1 C1 N2 -0.08(19) . . . . ?
C2 N1 C1 C8 178.36(13) . . . . ?
C1 N1 C2 C7 -0.10(18) . . . . ?
C1 N1 C2 C3 179.99(18) . . . . ?
C7 C2 C3 C4 -0.4(3) . . . . ?
N1 C2 C3 C4 179.48(17) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C4 C5 C6 C7 0.8(4) . . . . ?
N1 C2 C7 C6 -178.97(18) . . . . ?
C3 C2 C7 C6 1.0(3) . . . . ?
N1 C2 C7 N2 0.2(2) . . . . ?
C3 C2 C7 N2 -179.84(16) . . . . ?
C5 C6 C7 C2 -1.1(3) . . . . ?
C5 C6 C7 N2 179.9(2) . . . . ?
C1 N2 C7 C2 -0.3(2) . . . . ?
C1 N2 C7 C6 178.8(2) . . . . ?
N2 C1 C8 C9 82.1(2) . . . . ?
N1 C1 C8 C9 -96.20(19) . . . . ?
C10 N3 C9 N4 -0.09(15) . . . . ?
C10 N3 C9 C8 176.39(13) . . . . ?
C15 N4 C9 N3 0.07(16) . . . . ?
C15 N4 C9 C8 -176.38(12) . . . . ?
C1 C8 C9 N3 134.16(14) . . . . ?
C1 C8 C9 N4 -49.8(2) . . . . ?
C9 N3 C10 C11 -178.30(16) . . . . ?
C9 N3 C10 C15 0.08(15) . . . . ?
C15 C10 C11 C12 -0.5(2) . . . . ?
N3 C10 C11 C12 177.73(15) . . . . ?
C10 C11 C12 C13 0.4(3) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C12 C13 C14 C15 0.0(2) . . . . ?
C9 N4 C15 C10 -0.01(15) . . . . ?
C9 N4 C15 C14 177.81(15) . . . . ?
C11 C10 C15 N4 178.53(13) . . . . ?
N3 C10 C15 N4 -0.04(15) . . . . ?
C11 C10 C15 C14 0.4(2) . . . . ?
N3 C10 C15 C14 -178.14(12) . . . . ?
C13 C14 C15 N4 -177.62(15) . . . . ?
C13 C14 C15 C10 -0.1(2) . . . . ?
C17 N5 C16 N6 -0.16(16) . . . . ?
C17 N5 C16 C23 -176.83(12) . . . . ?
C22 N6 C16 N5 0.01(15) . . . . ?
C22 N6 C16 C23 176.79(12) . . . . ?
C16 N5 C17 C18 178.00(16) . . . . ?
C16 N5 C17 C22 0.25(16) . . . . ?
N5 C17 C18 C19 -177.23(15) . . . . ?
C22 C17 C18 C19 0.3(3) . . . . ?
C17 C18 C19 C20 0.1(3) . . . . ?
C18 C19 C20 C21 -0.3(3) . . . . ?
C19 C20 C21 C22 0.2(3) . . . . ?
C20 C21 C22 N6 177.41(16) . . . . ?
C20 C21 C22 C17 0.2(2) . . . . ?
C16 N6 C22 C21 -177.34(15) . . . . ?
C16 N6 C22 C17 0.15(15) . . . . ?
N5 C17 C22 C21 177.58(13) . . . . ?
C18 C17 C22 C21 -0.4(2) . . . . ?
N5 C17 C22 N6 -0.25(16) . . . . ?
C18 C17 C22 N6 -178.26(14) . . . . ?
N5 C16 C23 C24 -125.92(14) . . . . ?
N6 C16 C23 C24 57.70(18) . . . . ?
C25 N7 C24 N8 -1.07(19) . . . . ?
C25 N7 C24 C23 -179.58(15) . . . . ?
C30 N8 C24 N7 0.8(2) . . . . ?
C30 N8 C24 C23 179.31(15) . . . . ?
C16 C23 C24 N7 92.62(18) . . . . ?
C16 C23 C24 N8 -85.7(2) . . . . ?
C24 N7 C25 C30 1.0(2) . . . . ?
C24 N7 C25 C26 -179.22(19) . . . . ?
C30 C25 C26 C27 0.0(3) . . . . ?
N7 C25 C26 C27 -179.81(19) . . . . ?
C25 C26 C27 C28 1.1(4) . . . . ?
C26 C27 C28 C29 -1.4(4) . . . . ?
C27 C28 C29 C30 0.6(4) . . . . ?
N7 C25 C30 C29 179.1(2) . . . . ?
C26 C25 C30 C29 -0.8(3) . . . . ?
N7 C25 C30 N8 -0.5(2) . . . . ?
C26 C25 C30 N8 179.64(17) . . . . ?
C28 C29 C30 C25 0.5(4) . . . . ?
C28 C29 C30 N8 180.0(2) . . . . ?
C24 N8 C30 C25 -0.1(2) . . . . ?
C24 N8 C30 C29 -179.6(2) . . . . ?
C32 N9 C31 N10 0.30(19) . . . . ?
C32 N9 C31 C38 -178.30(14) . . . . ?
C37 N10 C31 N9 -0.31(19) . . . . ?
C37 N10 C31 C38 178.31(13) . . . . ?
C31 N9 C32 C37 -0.2(2) . . . . ?
C31 N9 C32 C33 178.8(2) . . . . ?
C37 C32 C33 C34 -1.0(4) . . . . ?
N9 C32 C33 C34 -179.8(2) . . . . ?
C32 C33 C34 C35 0.4(4) . . . . ?
C33 C34 C35 C36 0.0(5) . . . . ?
C34 C35 C36 C37 0.1(4) . . . . ?
C33 C32 C37 N10 -179.05(18) . . . . ?
N9 C32 C37 N10 0.0(2) . . . . ?
C33 C32 C37 C36 1.2(3) . . . . ?
N9 C32 C37 C36 -179.75(16) . . . . ?
C31 N10 C37 C32 0.17(18) . . . . ?
C31 N10 C37 C36 179.89(18) . . . . ?
C35 C36 C37 C32 -0.7(3) . . . . ?
C35 C36 C37 N10 179.59(18) . . . . ?
N9 C31 C38 C39 79.2(2) . . . . ?
N10 C31 C38 C39 -99.27(19) . . . . ?
C45 N12 C39 N11 -0.50(15) . . . . ?
C45 N12 C39 C38 176.52(13) . . . . ?
C40 N11 C39 N12 0.73(16) . . . . ?
C40 N11 C39 C38 -176.25(12) . . . . ?
C31 C38 C39 N12 133.03(15) . . . . ?
C31 C38 C39 N11 -50.3(2) . . . . ?
C39 N11 C40 C41 177.44(15) . . . . ?
C39 N11 C40 C45 -0.61(16) . . . . ?
N11 C40 C41 C42 -177.69(15) . . . . ?
C45 C40 C41 C42 0.0(2) . . . . ?
C40 C41 C42 C43 -0.3(2) . . . . ?
C41 C42 C43 C44 0.2(3) . . . . ?
C42 C43 C44 C45 0.3(3) . . . . ?
C43 C44 C45 C40 -0.5(2) . . . . ?
C43 C44 C45 N12 177.49(15) . . . . ?
N11 C40 C45 C44 178.70(13) . . . . ?
C41 C40 C45 C44 0.4(2) . . . . ?
N11 C40 C45 N12 0.33(16) . . . . ?
C41 C40 C45 N12 -177.98(13) . . . . ?
C39 N12 C45 C44 -178.06(16) . . . . ?
C39 N12 C45 C40 0.09(15) . . . . ?
C47 N13 C46 N14 -0.4(2) . . . . ?
C47 N13 C46 C53 179.11(15) . . . . ?
C52 N14 C46 N13 -0.1(2) . . . . ?
C52 N14 C46 C53 -179.57(14) . . . . ?
C46 N13 C47 C52 0.7(2) . . . . ?
C46 N13 C47 C48 -178.9(2) . . . . ?
C52 C47 C48 C49 0.0(3) . . . . ?
N13 C47 C48 C49 179.5(2) . . . . ?
C47 C48 C49 C50 1.1(4) . . . . ?
C48 C49 C50 C51 -1.6(4) . . . . ?
C49 C50 C51 C52 1.0(4) . . . . ?
C48 C47 C52 N14 178.87(19) . . . . ?
N13 C47 C52 N14 -0.7(2) . . . . ?
C48 C47 C52 C51 -0.6(3) . . . . ?
N13 C47 C52 C51 179.84(16) . . . . ?
C46 N14 C52 C47 0.50(19) . . . . ?
C46 N14 C52 C51 179.84(19) . . . . ?
C50 C51 C52 C47 0.0(3) . . . . ?
C50 C51 C52 N14 -179.21(19) . . . . ?
N13 C46 C53 C54 -77.8(2) . . . . ?
N14 C46 C53 C54 101.59(17) . . . . ?
C55 N15 C54 N16 0.51(15) . . . . ?
C55 N15 C54 C53 177.64(12) . . . . ?
C60 N16 C54 N15 -1.00(16) . . . . ?
C60 N16 C54 C53 -178.17(12) . . . . ?
C46 C53 C54 N15 52.62(19) . . . . ?
C46 C53 C54 N16 -130.51(14) . . . . ?
C54 N15 C55 C56 -178.49(15) . . . . ?
C54 N15 C55 C60 0.16(16) . . . . ?
C60 C55 C56 C57 -0.4(2) . . . . ?
N15 C55 C56 C57 178.17(15) . . . . ?
C55 C56 C57 C58 0.1(3) . . . . ?
C56 C57 C58 C59 -0.2(3) . . . . ?
C57 C58 C59 C60 0.6(3) . . . . ?
C54 N16 C60 C59 177.93(17) . . . . ?
C54 N16 C60 C55 0.99(15) . . . . ?
C58 C59 C60 N16 -177.33(15) . . . . ?
C58 C59 C60 C55 -0.9(3) . . . . ?
C56 C55 C60 N16 178.11(12) . . . . ?
N15 C55 C60 N16 -0.72(16) . . . . ?
C56 C55 C60 C59 0.8(2) . . . . ?
N15 C55 C60 C59 -178.01(15) . . . . ?


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

# start Validation Reply Form
_vrf_PLAT029_BI2C_RT             
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.658 Why?  
RESPONSE:
The data have been collected on 1-circle goniometer with IP area detector 
diffractometer. It is only the very high angle data that is incomplete due to 
the shape of the area detector, and we have ca. 100% coverage in the low angle 
data. This will always be a problem with area detector data that is not 
truncated. In addition, changing the direction of crystal is difficult 
due to the N2 blower for the temperaature control. The obtained 
analysis was sufficient to elucidate the molecular structure. 
;
_vrf_PLAT110_BI2C_RT             
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ...          ? Check 
RESPONSE: 
The crystal has pseudo symmetry of the tetragonal I-lattice. However,
the diffraction pattern shows monoclinic in this temperature phase,
clearly.
;
_vrf_PLAT112_BI2C_RT             
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem        43        100 %Fit  
RESPONSE: 
The crystal has pseudo symmetry of the tetragonal I-lattice. However,
the diffraction pattern shows monoclinic in this temperature phase,
clearly.
;
_vrf_PLAT113_BI2C_RT             
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group      I41/a Check 
RESPONSE:
The crystal has pseudo symmetry of the tetragonal I-lattice. However,
the diffraction pattern shows monoclinic, clearly.  We confirmed the 
symmentry of the crystal carefully and determined the space group.
;
_vrf_PLAT911_BI2C_RT             
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600       3265 Report
RESPONSE: 
A part of the data are missing by the blind area due to the cooling device. 
;
# end Validation Reply Form



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        bis-(1H-benzimidazol-2-yl)-methane
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_BI2C-d2
_database_code_depnum_ccdc_archive 'CCDC 1989817'
loop_
_audit_author_name
_audit_author_address
'Sachio Horiuchi'
;National Institute of Advanced Science and Technology 
Japan
;
_audit_update_record             
;
2020-03-11 deposited with the CCDC.	2020-05-13 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C15 H12 N4'
_chemical_formula_moiety         'C15 H12 N4'
_chemical_formula_weight         248.29
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      tetragonal
_space_group_name_H-M_alt        'P 43'
_space_group_name_Hall           'P 4cw'
_space_group_IT_number           78
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,1/2+Z
3 -Y,+X,3/4+Z
4 +Y,-X,1/4+Z
#------------------------------------------------------------------------------
_cell_length_a                   18.3126(4)
_cell_length_b                   18.3126(4)
_cell_length_c                   15.7252(5)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     5273.5(2)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    8307
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      29.86
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       octahedral
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.330
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2080.00
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.931
_exptl_absorpt_correction_T_max  0.974

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

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_reflns_number            21499
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0105
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_min         2.487
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             11425
_reflns_number_gt                7162
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.832
_reflns_Friedel_fraction_max     0.891
_reflns_Friedel_fraction_full    0.910

#==============================================================================
# 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          0.0824
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1527
_refine_ls_wR_factor_gt          0.1319
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         11425
_refine_ls_number_parameters     685
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0916P)²] 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         0.17
_refine_diff_density_min         -0.16
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 2685 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(10)

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 0.07168(18) 0.83018(19) 0.4671(2) 0.0484(9) Uani 1 1 d . . . . .
H3B H 0.025723 0.828747 0.456032 0.058 Uiso 1 1 calc R U . . .
N2 N 0.19141(18) 0.8196(2) 0.4493(3) 0.0614(11) Uani 1 1 d . . . . .
N3 N 0.06513(17) 0.65689(19) 0.2880(2) 0.0492(9) Uani 1 1 d . . . . .
H8A H 0.024378 0.671867 0.267124 0.059 Uiso 1 1 calc R U . . .
N4 N 0.17444(18) 0.6610(2) 0.3487(2) 0.0493(9) Uani 1 1 d . . . . .
N5 N 0.31903(17) 0.8393(2) 0.3534(2) 0.0491(9) Uani 1 1 d . . . . .
H15A H 0.280753 0.824269 0.379863 0.059 Uiso 1 1 calc R U . . .
N6 N 0.42528(17) 0.83519(18) 0.2854(2) 0.0467(8) Uani 1 1 d . . . . .
N7 N 0.29981(18) 0.6743(2) 0.4552(3) 0.0621(11) Uani 1 1 d . . . . .
H20A H 0.257532 0.681335 0.432878 0.075 Uiso 1 1 calc R U . . .
N8 N 0.42010(18) 0.6701(2) 0.4668(2) 0.0476(9) Uani 1 1 d . . . . .
N9 N 0.57092(18) 0.83047(18) 0.2336(2) 0.0464(9) Uani 1 1 d . . . . .
H27A H 0.524755 0.827501 0.242988 0.056 Uiso 1 1 calc R U . . .
N10 N 0.68919(19) 0.8216(2) 0.2566(2) 0.0606(11) Uani 1 1 d . . . . .
N11 N 0.56621(19) 0.6598(2) 0.4172(2) 0.0524(9) Uani 1 1 d . . . . .
H32A H 0.525399 0.674655 0.437977 0.063 Uiso 1 1 calc R U . . .
N12 N 0.67403(17) 0.6638(2) 0.3540(2) 0.0506(9) Uani 1 1 d . . . . .
N13 N 0.81871(16) 0.84207(19) 0.3496(2) 0.0475(9) Uani 1 1 d . . . . .
H39B H 0.780829 0.827486 0.322069 0.057 Uiso 1 1 calc R U . . .
N14 N 0.92425(18) 0.83754(19) 0.4180(2) 0.0486(9) Uani 1 1 d . . . . .
N15 N 0.8013(2) 0.6789(2) 0.2502(3) 0.0628(11) Uani 1 1 d . . . . .
H44A H 0.759616 0.688942 0.272402 0.075 Uiso 1 1 calc R U . . .
N16 N 0.92077(19) 0.6696(2) 0.2364(2) 0.0516(10) Uani 1 1 d . . . . .
C1 C 0.1109(2) 0.7803(2) 0.3301(3) 0.0505(10) Uani 1 1 d . . . . .
H1A H 0.145218 0.802172 0.290603 0.061 Uiso 1 1 calc R U . . .
H2C H 0.062186 0.794465 0.312377 0.061 Uiso 1 1 calc R U . . .
C2 C 0.1247(2) 0.8103(2) 0.4156(3) 0.0461(11) Uani 1 1 d . . . . .
C3 C 0.1036(2) 0.8543(3) 0.5440(3) 0.0503(11) Uani 1 1 d . . . . .
C4 C 0.0750(3) 0.8817(3) 0.6167(3) 0.0744(15) Uani 1 1 d . . . . .
H4A H 0.024932 0.888232 0.622998 0.089 Uiso 1 1 calc R U . . .
C5 C 0.1228(3) 0.8996(3) 0.6811(4) 0.091(2) Uani 1 1 d . . . . .
H5B H 0.104469 0.918737 0.731597 0.109 Uiso 1 1 calc R U . . .
C6 C 0.1964(3) 0.8899(4) 0.6725(4) 0.100(2) Uani 1 1 d . . . . .
H6A H 0.226998 0.898112 0.718754 0.121 Uiso 1 1 calc R U . . .
C7 C 0.2268(3) 0.8672(3) 0.5928(4) 0.104(2) Uani 1 1 d . . . . .
H7B H 0.276902 0.866527 0.582960 0.125 Uiso 1 1 calc R U . . .
C8 C 0.1765(2) 0.8461(3) 0.5310(3) 0.0539(11) Uani 1 1 d . . . . .
C9 C 0.1172(2) 0.6984(3) 0.3236(2) 0.0448(10) Uani 1 1 d . . . . .
C10 C 0.0893(2) 0.5859(3) 0.2911(3) 0.0492(11) Uani 1 1 d . . . . .
C11 C 0.0596(2) 0.5217(3) 0.2610(3) 0.0655(14) Uani 1 1 d . . . . .
H9B H 0.013904 0.520653 0.235301 0.079 Uiso 1 1 calc R U . . .
C12 C 0.1002(3) 0.4597(3) 0.2705(4) 0.0754(15) Uani 1 1 d . . . . .
H10A H 0.081766 0.415569 0.250579 0.090 Uiso 1 1 calc R U . . .
C13 C 0.1673(3) 0.4607(3) 0.3085(3) 0.0721(16) Uani 1 1 d . . . . .
H11C H 0.192747 0.417046 0.314307 0.086 Uiso 1 1 calc R U . . .
C14 C 0.1989(3) 0.5248(3) 0.3390(3) 0.0658(14) Uani 1 1 d . . . . .
H12A H 0.244816 0.525068 0.364432 0.079 Uiso 1 1 calc R U . . .
C15 C 0.1578(2) 0.5890(3) 0.3293(3) 0.0464(11) Uani 1 1 d . . . . .
C16 C 0.3735(2) 0.7157(2) 0.3312(3) 0.0497(10) Uani 1 1 d . . . . .
H13A H 0.333834 0.696768 0.296774 0.060 Uiso 1 1 calc R U . . .
H14B H 0.418756 0.697507 0.307024 0.060 Uiso 1 1 calc R U . . .
C17 C 0.3735(2) 0.7975(3) 0.3240(3) 0.0438(10) Uani 1 1 d . . . . .
C18 C 0.3355(2) 0.9105(3) 0.3337(3) 0.0471(11) Uani 1 1 d . . . . .
C19 C 0.2981(2) 0.9760(2) 0.3458(3) 0.0630(13) Uani 1 1 d . . . . .
H16A H 0.253880 0.978123 0.374812 0.076 Uiso 1 1 calc R U . . .
C20 C 0.3309(3) 1.0381(3) 0.3119(3) 0.0695(15) Uani 1 1 d . . . . .
H17A H 0.307926 1.083020 0.318414 0.083 Uiso 1 1 calc R U . . .
C21 C 0.3966(3) 1.0350(3) 0.2691(3) 0.0681(14) Uani 1 1 d . . . . .
H18A H 0.416371 1.077756 0.246947 0.082 Uiso 1 1 calc R U . . .
C22 C 0.4333(2) 0.9705(3) 0.2583(3) 0.0605(13) Uani 1 1 d . . . . .
H19A H 0.477747 0.968969 0.229777 0.073 Uiso 1 1 calc R U . . .
C23 C 0.4018(2) 0.9071(2) 0.2915(3) 0.0466(10) Uani 1 1 d . . . . .
C24 C 0.3660(2) 0.6858(2) 0.4184(3) 0.0459(11) Uani 1 1 d . . . . .
C25 C 0.3148(3) 0.6491(3) 0.5360(3) 0.0575(12) Uani 1 1 d . . . . .
C26 C 0.2667(3) 0.6261(4) 0.5985(4) 0.112(2) Uani 1 1 d . . . . .
H21A H 0.216470 0.624310 0.589987 0.135 Uiso 1 1 calc R U . . .
C27 C 0.3004(3) 0.6051(4) 0.6775(4) 0.103(2) Uani 1 1 d . . . . .
H22A H 0.271413 0.595365 0.724767 0.124 Uiso 1 1 calc R U . . .
C28 C 0.3749(3) 0.5994(3) 0.6836(4) 0.0852(19) Uani 1 1 d . . . . .
H23A H 0.395663 0.581828 0.733534 0.102 Uiso 1 1 calc R U . . .
C29 C 0.4195(3) 0.6194(3) 0.6166(3) 0.0711(14) Uani 1 1 d . . . . .
H24A H 0.469988 0.615281 0.621021 0.085 Uiso 1 1 calc R U . . .
C30 C 0.3883(2) 0.6453(3) 0.5442(3) 0.0478(11) Uani 1 1 d . . . . .
C31 C 0.6100(2) 0.7832(2) 0.3771(2) 0.0518(10) Uani 1 1 d . . . . .
H25A H 0.643582 0.805208 0.417272 0.062 Uiso 1 1 calc R U . . .
H26B H 0.560809 0.797134 0.393366 0.062 Uiso 1 1 calc R U . . .
C32 C 0.6258(2) 0.8120(2) 0.2894(3) 0.0429(10) Uani 1 1 d . . . . .
C33 C 0.6029(2) 0.8540(3) 0.1616(3) 0.0470(11) Uani 1 1 d . . . . .
C34 C 0.5738(3) 0.8786(3) 0.0832(3) 0.0577(12) Uani 1 1 d . . . . .
H28A H 0.523706 0.881210 0.073858 0.069 Uiso 1 1 calc R U . . .
C35 C 0.6228(3) 0.8981(3) 0.0222(4) 0.0799(17) Uani 1 1 d . . . . .
H29A H 0.606189 0.914317 -0.030397 0.096 Uiso 1 1 calc R U . . .
C36 C 0.6982(3) 0.8941(4) 0.0379(4) 0.107(2) Uani 1 1 d . . . . .
H30A H 0.730136 0.911791 -0.003164 0.128 Uiso 1 1 calc R U . . .
C37 C 0.7254(3) 0.8666(3) 0.1079(4) 0.0884(18) Uani 1 1 d . . . . .
H31B H 0.775313 0.858414 0.112756 0.106 Uiso 1 1 calc R U . . .
C38 C 0.6788(3) 0.8495(3) 0.1751(3) 0.0606(13) Uani 1 1 d . . . . .
C39 C 0.6169(2) 0.7025(3) 0.3812(2) 0.0426(10) Uani 1 1 d . . . . .
C40 C 0.5897(2) 0.5884(3) 0.4155(2) 0.0491(11) Uani 1 1 d . . . . .
C41 C 0.5600(3) 0.5236(3) 0.4442(4) 0.0715(15) Uani 1 1 d . . . . .
H33A H 0.514416 0.522185 0.470086 0.086 Uiso 1 1 calc R U . . .
C42 C 0.6011(3) 0.4610(3) 0.4327(4) 0.0756(15) Uani 1 1 d . . . . .
H34A H 0.582806 0.416293 0.450912 0.091 Uiso 1 1 calc R U . . .
C43 C 0.6697(3) 0.4643(3) 0.3940(3) 0.0701(16) Uani 1 1 d . . . . .
H35A H 0.696650 0.421588 0.387577 0.084 Uiso 1 1 calc R U . . .
C44 C 0.6981(2) 0.5285(3) 0.3654(3) 0.0616(13) Uani 1 1 d . . . . .
H36A H 0.743696 0.529610 0.339354 0.074 Uiso 1 1 calc R U . . .
C45 C 0.6582(2) 0.5920(3) 0.3756(3) 0.0485(11) Uani 1 1 d . . . . .
C46 C 0.8728(2) 0.7178(2) 0.3765(3) 0.0531(11) Uani 1 1 d . . . . .
H37A H 0.832689 0.699741 0.410777 0.064 Uiso 1 1 calc R U . . .
H38B H 0.917836 0.699439 0.400870 0.064 Uiso 1 1 calc R U . . .
C47 C 0.8734(2) 0.7991(3) 0.3803(2) 0.0427(10) Uani 1 1 d . . . . .
C48 C 0.8353(2) 0.9134(3) 0.3708(3) 0.0470(11) Uani 1 1 d . . . . .
C49 C 0.7984(2) 0.9779(3) 0.3591(3) 0.0608(13) Uani 1 1 d . . . . .
H40A H 0.753737 0.979320 0.331057 0.073 Uiso 1 1 calc R U . . .
C50 C 0.8298(3) 1.0399(3) 0.3903(3) 0.0712(16) Uani 1 1 d . . . . .
H41A H 0.805523 1.084177 0.384104 0.085 Uiso 1 1 calc R U . . .
C51 C 0.8975(3) 1.0385(3) 0.4314(4) 0.0755(15) Uani 1 1 d . . . . .
H42A H 0.918217 1.081886 0.450591 0.091 Uiso 1 1 calc R U . . .
C52 C 0.9339(3) 0.9733(3) 0.4437(4) 0.0711(15) Uani 1 1 d . . . . .
H43A H 0.978637 0.972074 0.471707 0.085 Uiso 1 1 calc R U . . .
C53 C 0.9024(2) 0.9100(3) 0.4136(2) 0.0494(11) Uani 1 1 d . . . . .
C54 C 0.8651(2) 0.6886(2) 0.2873(3) 0.0405(10) Uani 1 1 d . . . . .
C55 C 0.8120(2) 0.6500(3) 0.1698(3) 0.0619(14) Uani 1 1 d . . . . .
C56 C 0.7686(3) 0.6322(3) 0.1011(4) 0.093(2) Uani 1 1 d . . . . .
H45A H 0.718486 0.640001 0.102636 0.112 Uiso 1 1 calc R U . . .
C57 C 0.7996(3) 0.6041(4) 0.0338(5) 0.114(3) Uani 1 1 d . . . . .
H46A H 0.769844 0.586365 -0.009451 0.137 Uiso 1 1 calc R U . . .
C58 C 0.8753(3) 0.5995(3) 0.0234(4) 0.0880(19) Uani 1 1 d . . . . .
H47A H 0.894413 0.582438 -0.027592 0.106 Uiso 1 1 calc R U . . .
C59 C 0.9211(3) 0.6197(3) 0.0871(3) 0.0668(13) Uani 1 1 d . . . . .
H48A H 0.971506 0.616655 0.080773 0.080 Uiso 1 1 calc R U . . .
C60 C 0.8889(2) 0.6457(3) 0.1640(3) 0.0491(11) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_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 C2 1.315(5) . ?
N1 C3 1.413(5) . ?
N1 H3B 0.8600 . ?
N2 C2 1.343(5) . ?
N2 C8 1.401(6) . ?
N3 C9 1.343(5) . ?
N3 C10 1.373(5) . ?
N3 H8A 0.8600 . ?
N4 C9 1.313(5) . ?
N4 C15 1.388(6) . ?
N5 C17 1.338(5) . ?
N5 C18 1.375(6) . ?
N5 H15A 0.8600 . ?
N6 C17 1.321(5) . ?
N6 C23 1.388(5) . ?
N7 C24 1.360(5) . ?
N7 C25 1.380(6) . ?
N7 H20A 0.8600 . ?
N8 C24 1.282(5) . ?
N8 C30 1.424(5) . ?
N9 C33 1.345(5) . ?
N9 C32 1.377(5) . ?
N9 H27A 0.8600 . ?
N10 C32 1.282(5) . ?
N10 C38 1.393(6) . ?
N11 C39 1.339(5) . ?
N11 C40 1.377(5) . ?
N11 H32A 0.8600 . ?
N12 C39 1.334(5) . ?
N12 C45 1.388(6) . ?
N13 C47 1.363(5) . ?
N13 C48 1.382(6) . ?
N13 H39B 0.8600 . ?
N14 C47 1.309(5) . ?
N14 C53 1.387(5) . ?
N15 C54 1.317(5) . ?
N15 C55 1.384(6) . ?
N15 H44A 0.8600 . ?
N16 C54 1.342(5) . ?
N16 C60 1.352(6) . ?
C1 C2 1.475(6) . ?
C1 C9 1.506(6) . ?
C1 H1A 0.9700 . ?
C1 H2C 0.9700 . ?
C3 C4 1.354(6) . ?
C3 C8 1.359(6) . ?
C4 C5 1.377(7) . ?
C4 H4A 0.9300 . ?
C5 C6 1.367(7) . ?
C5 H5B 0.9300 . ?
C6 C7 1.434(8) . ?
C6 H6A 0.9300 . ?
C7 C8 1.394(6) . ?
C7 H7B 0.9300 . ?
C10 C11 1.379(6) . ?
C10 C15 1.392(6) . ?
C11 C12 1.366(7) . ?
C11 H9B 0.9300 . ?
C12 C13 1.365(7) . ?
C12 H10A 0.9300 . ?
C13 C14 1.395(6) . ?
C13 H11C 0.9300 . ?
C14 C15 1.404(6) . ?
C14 H12A 0.9300 . ?
C16 C24 1.483(6) . ?
C16 C17 1.503(6) . ?
C16 H13A 0.9700 . ?
C16 H14B 0.9700 . ?
C18 C23 1.383(6) . ?
C18 C19 1.395(6) . ?
C19 C20 1.392(6) . ?
C19 H16A 0.9300 . ?
C20 C21 1.379(7) . ?
C20 H17A 0.9300 . ?
C21 C22 1.369(6) . ?
C21 H18A 0.9300 . ?
C22 C23 1.399(6) . ?
C22 H19A 0.9300 . ?
C25 C30 1.354(6) . ?
C25 C26 1.384(7) . ?
C26 C27 1.440(8) . ?
C26 H21A 0.9300 . ?
C27 C28 1.372(7) . ?
C27 H22A 0.9300 . ?
C28 C29 1.383(7) . ?
C28 H23A 0.9300 . ?
C29 C30 1.359(6) . ?
C29 H24A 0.9300 . ?
C31 C39 1.485(6) . ?
C31 C32 1.504(6) . ?
C31 H25A 0.9700 . ?
C31 H26B 0.9700 . ?
C33 C38 1.408(6) . ?
C33 C34 1.417(6) . ?
C34 C35 1.362(7) . ?
C34 H28A 0.9300 . ?
C35 C36 1.404(7) . ?
C35 H29A 0.9300 . ?
C36 C37 1.310(8) . ?
C36 H30A 0.9300 . ?
C37 C38 1.393(7) . ?
C37 H31B 0.9300 . ?
C40 C41 1.379(6) . ?
C40 C45 1.405(6) . ?
C41 C42 1.383(7) . ?
C41 H33A 0.9300 . ?
C42 C43 1.398(7) . ?
C42 H34A 0.9300 . ?
C43 C44 1.362(6) . ?
C43 H35A 0.9300 . ?
C44 C45 1.383(6) . ?
C44 H36A 0.9300 . ?
C46 C47 1.489(6) . ?
C46 C54 1.508(6) . ?
C46 H37A 0.9700 . ?
C46 H38B 0.9700 . ?
C48 C49 1.373(6) . ?
C48 C53 1.403(6) . ?
C49 C50 1.362(7) . ?
C49 H40A 0.9300 . ?
C50 C51 1.399(7) . ?
C50 H41A 0.9300 . ?
C51 C52 1.382(7) . ?
C51 H42A 0.9300 . ?
C52 C53 1.379(6) . ?
C52 H43A 0.9300 . ?
C55 C56 1.380(7) . ?
C55 C60 1.413(6) . ?
C56 C57 1.306(8) . ?
C56 H45A 0.9300 . ?
C57 C58 1.397(7) . ?
C57 H46A 0.9300 . ?
C58 C59 1.357(7) . ?
C58 H47A 0.9300 . ?
C59 C60 1.428(6) . ?
C59 H48A 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
C2 N1 C3 108.0(3) . . ?
C2 N1 H3B 126.0 . . ?
C3 N1 H3B 126.0 . . ?
C2 N2 C8 103.2(4) . . ?
C9 N3 C10 107.0(3) . . ?
C9 N3 H8A 126.5 . . ?
C10 N3 H8A 126.5 . . ?
C9 N4 C15 104.8(3) . . ?
C17 N5 C18 107.5(4) . . ?
C17 N5 H15A 126.3 . . ?
C18 N5 H15A 126.3 . . ?
C17 N6 C23 103.9(3) . . ?
C24 N7 C25 105.5(4) . . ?
C24 N7 H20A 127.3 . . ?
C25 N7 H20A 127.3 . . ?
C24 N8 C30 105.3(3) . . ?
C33 N9 C32 107.3(3) . . ?
C33 N9 H27A 126.3 . . ?
C32 N9 H27A 126.4 . . ?
C32 N10 C38 107.3(4) . . ?
C39 N11 C40 109.3(4) . . ?
C39 N11 H32A 125.3 . . ?
C40 N11 H32A 125.4 . . ?
C39 N12 C45 105.2(3) . . ?
C47 N13 C48 107.4(3) . . ?
C47 N13 H39B 126.3 . . ?
C48 N13 H39B 126.3 . . ?
C47 N14 C53 106.6(3) . . ?
C54 N15 C55 109.3(4) . . ?
C54 N15 H44A 125.3 . . ?
C55 N15 H44A 125.4 . . ?
C54 N16 C60 104.9(3) . . ?
C2 C1 C9 114.8(4) . . ?
C2 C1 H1A 108.6 . . ?
C9 C1 H1A 108.5 . . ?
C2 C1 H2C 108.6 . . ?
C9 C1 H2C 108.6 . . ?
H1A C1 H2C 107.5 . . ?
N1 C2 N2 113.2(4) . . ?
N1 C2 C1 122.6(4) . . ?
N2 C2 C1 124.2(4) . . ?
C4 C3 C8 123.2(4) . . ?
C4 C3 N1 132.7(4) . . ?
C8 C3 N1 104.1(4) . . ?
C3 C4 C5 117.6(5) . . ?
C3 C4 H4A 121.3 . . ?
C5 C4 H4A 121.1 . . ?
C6 C5 C4 121.5(5) . . ?
C6 C5 H5B 119.2 . . ?
C4 C5 H5B 119.2 . . ?
C5 C6 C7 120.5(5) . . ?
C5 C6 H6A 119.7 . . ?
C7 C6 H6A 119.8 . . ?
C8 C7 C6 115.6(5) . . ?
C8 C7 H7B 122.2 . . ?
C6 C7 H7B 122.1 . . ?
C3 C8 C7 121.0(4) . . ?
C3 C8 N2 111.6(4) . . ?
C7 C8 N2 127.3(4) . . ?
N4 C9 N3 113.4(4) . . ?
N4 C9 C1 124.1(4) . . ?
N3 C9 C1 122.5(4) . . ?
N3 C10 C11 131.9(4) . . ?
N3 C10 C15 105.5(4) . . ?
C11 C10 C15 122.5(5) . . ?
C12 C11 C10 117.2(5) . . ?
C12 C11 H9B 121.3 . . ?
C10 C11 H9B 121.4 . . ?
C13 C12 C11 121.7(5) . . ?
C13 C12 H10A 119.2 . . ?
C11 C12 H10A 119.1 . . ?
C12 C13 C14 122.4(5) . . ?
C12 C13 H11C 118.8 . . ?
C14 C13 H11C 118.8 . . ?
C13 C14 C15 116.3(5) . . ?
C13 C14 H12A 121.8 . . ?
C15 C14 H12A 121.9 . . ?
N4 C15 C10 109.3(4) . . ?
N4 C15 C14 130.8(4) . . ?
C10 C15 C14 119.8(5) . . ?
C24 C16 C17 115.9(4) . . ?
C24 C16 H13A 108.3 . . ?
C17 C16 H13A 108.2 . . ?
C24 C16 H14B 108.3 . . ?
C17 C16 H14B 108.3 . . ?
H13A C16 H14B 107.4 . . ?
N6 C17 N5 113.3(4) . . ?
N6 C17 C16 123.7(4) . . ?
N5 C17 C16 123.0(4) . . ?
N5 C18 C23 104.9(4) . . ?
N5 C18 C19 132.6(4) . . ?
C23 C18 C19 122.4(4) . . ?
C20 C19 C18 115.9(5) . . ?
C20 C19 H16A 122.0 . . ?
C18 C19 H16A 122.1 . . ?
C21 C20 C19 122.0(5) . . ?
C21 C20 H17A 119.0 . . ?
C19 C20 H17A 119.0 . . ?
C22 C21 C20 121.6(5) . . ?
C22 C21 H18A 119.2 . . ?
C20 C21 H18A 119.3 . . ?
C21 C22 C23 117.9(5) . . ?
C21 C22 H19A 121.0 . . ?
C23 C22 H19A 121.1 . . ?
C18 C23 N6 110.4(4) . . ?
C18 C23 C22 120.2(5) . . ?
N6 C23 C22 129.3(4) . . ?
N8 C24 N7 113.6(4) . . ?
N8 C24 C16 124.1(4) . . ?
N7 C24 C16 122.2(4) . . ?
C30 C25 N7 107.6(4) . . ?
C30 C25 C26 123.3(4) . . ?
N7 C25 C26 129.0(4) . . ?
C25 C26 C27 114.9(5) . . ?
C25 C26 H21A 122.6 . . ?
C27 C26 H21A 122.5 . . ?
C28 C27 C26 120.4(5) . . ?
C28 C27 H22A 119.7 . . ?
C26 C27 H22A 119.9 . . ?
C27 C28 C29 121.0(5) . . ?
C27 C28 H23A 119.5 . . ?
C29 C28 H23A 119.5 . . ?
C30 C29 C28 118.8(5) . . ?
C30 C29 H24A 120.7 . . ?
C28 C29 H24A 120.5 . . ?
C25 C30 C29 121.1(4) . . ?
C25 C30 N8 108.0(4) . . ?
C29 C30 N8 130.9(4) . . ?
C39 C31 C32 111.9(4) . . ?
C39 C31 H25A 109.3 . . ?
C32 C31 H25A 109.2 . . ?
C39 C31 H26B 109.2 . . ?
C32 C31 H26B 109.2 . . ?
H25A C31 H26B 107.9 . . ?
N10 C32 N9 111.8(4) . . ?
N10 C32 C31 126.3(4) . . ?
N9 C32 C31 122.0(4) . . ?
N9 C33 C38 106.5(4) . . ?
N9 C33 C34 132.1(4) . . ?
C38 C33 C34 121.4(4) . . ?
C35 C34 C33 116.6(4) . . ?
C35 C34 H28A 121.8 . . ?
C33 C34 H28A 121.6 . . ?
C34 C35 C36 120.7(5) . . ?
C34 C35 H29A 119.6 . . ?
C36 C35 H29A 119.7 . . ?
C37 C36 C35 122.8(5) . . ?
C37 C36 H30A 118.5 . . ?
C35 C36 H30A 118.7 . . ?
C36 C37 C38 119.4(5) . . ?
C36 C37 H31B 120.4 . . ?
C38 C37 H31B 120.2 . . ?
C37 C38 N10 134.1(4) . . ?
C37 C38 C33 118.5(4) . . ?
N10 C38 C33 107.1(4) . . ?
N12 C39 N11 111.6(4) . . ?
N12 C39 C31 125.6(4) . . ?
N11 C39 C31 122.7(4) . . ?
N11 C40 C41 133.4(4) . . ?
N11 C40 C45 104.0(4) . . ?
C41 C40 C45 122.6(5) . . ?
C40 C41 C42 117.1(5) . . ?
C40 C41 H33A 121.4 . . ?
C42 C41 H33A 121.5 . . ?
C41 C42 C43 120.7(5) . . ?
C41 C42 H34A 119.7 . . ?
C43 C42 H34A 119.6 . . ?
C44 C43 C42 121.6(5) . . ?
C44 C43 H35A 119.2 . . ?
C42 C43 H35A 119.2 . . ?
C43 C44 C45 119.1(5) . . ?
C43 C44 H36A 120.5 . . ?
C45 C44 H36A 120.4 . . ?
C44 C45 N12 131.1(4) . . ?
C44 C45 C40 119.0(5) . . ?
N12 C45 C40 109.9(4) . . ?
C47 C46 C54 113.2(3) . . ?
C47 C46 H37A 109.0 . . ?
C54 C46 H37A 108.9 . . ?
C47 C46 H38B 108.9 . . ?
C54 C46 H38B 108.9 . . ?
H37A C46 H38B 107.8 . . ?
N14 C47 N13 111.9(4) . . ?
N14 C47 C46 124.1(4) . . ?
N13 C47 C46 123.9(4) . . ?
C49 C48 N13 132.3(4) . . ?
C49 C48 C53 122.3(5) . . ?
N13 C48 C53 105.4(4) . . ?
C50 C49 C48 117.4(5) . . ?
C50 C49 H40A 121.3 . . ?
C48 C49 H40A 121.2 . . ?
C49 C50 C51 121.7(5) . . ?
C49 C50 H41A 119.1 . . ?
C51 C50 H41A 119.2 . . ?
C52 C51 C50 120.5(5) . . ?
C52 C51 H42A 119.8 . . ?
C50 C51 H42A 119.7 . . ?
C53 C52 C51 118.5(5) . . ?
C53 C52 H43A 120.7 . . ?
C51 C52 H43A 120.8 . . ?
C52 C53 N14 131.7(4) . . ?
C52 C53 C48 119.6(5) . . ?
N14 C53 C48 108.7(4) . . ?
N15 C54 N16 112.0(4) . . ?
N15 C54 C46 122.9(4) . . ?
N16 C54 C46 125.0(4) . . ?
C56 C55 N15 136.4(4) . . ?
C56 C55 C60 120.7(4) . . ?
N15 C55 C60 102.8(4) . . ?
C57 C56 C55 118.5(5) . . ?
C57 C56 H45A 120.8 . . ?
C55 C56 H45A 120.7 . . ?
C56 C57 C58 123.3(5) . . ?
C56 C57 H46A 118.3 . . ?
C58 C57 H46A 118.4 . . ?
C59 C58 C57 120.7(5) . . ?
C59 C58 H47A 119.6 . . ?
C57 C58 H47A 119.6 . . ?
C58 C59 C60 117.4(4) . . ?
C58 C59 H48A 121.4 . . ?
C60 C59 H48A 121.2 . . ?
N16 C60 C55 111.0(4) . . ?
N16 C60 C59 130.1(4) . . ?
C55 C60 C59 118.9(4) . . ?

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 N1 C2 N2 -1.1(6) . . . . ?
C3 N1 C2 C1 178.4(4) . . . . ?
C8 N2 C2 N1 1.8(6) . . . . ?
C8 N2 C2 C1 -177.6(4) . . . . ?
C9 C1 C2 N1 -101.2(5) . . . . ?
C9 C1 C2 N2 78.2(5) . . . . ?
C2 N1 C3 C4 178.4(6) . . . . ?
C2 N1 C3 C8 -0.2(5) . . . . ?
C8 C3 C4 C5 -2.2(10) . . . . ?
N1 C3 C4 C5 179.4(5) . . . . ?
C3 C4 C5 C6 -0.3(11) . . . . ?
C4 C5 C6 C7 6.0(11) . . . . ?
C5 C6 C7 C8 -8.9(11) . . . . ?
C4 C3 C8 C7 -1.2(9) . . . . ?
N1 C3 C8 C7 177.6(5) . . . . ?
C4 C3 C8 N2 -177.4(5) . . . . ?
N1 C3 C8 N2 1.4(6) . . . . ?
C6 C7 C8 C3 6.6(9) . . . . ?
C6 C7 C8 N2 -177.9(5) . . . . ?
C2 N2 C8 C3 -2.0(6) . . . . ?
C2 N2 C8 C7 -177.8(6) . . . . ?
C15 N4 C9 N3 -1.1(5) . . . . ?
C15 N4 C9 C1 -178.7(4) . . . . ?
C10 N3 C9 N4 1.1(5) . . . . ?
C10 N3 C9 C1 178.7(4) . . . . ?
C2 C1 C9 N4 -53.1(5) . . . . ?
C2 C1 C9 N3 129.6(5) . . . . ?
C9 N3 C10 C11 -177.0(5) . . . . ?
C9 N3 C10 C15 -0.6(5) . . . . ?
N3 C10 C11 C12 176.3(5) . . . . ?
C15 C10 C11 C12 0.4(7) . . . . ?
C10 C11 C12 C13 0.3(8) . . . . ?
C11 C12 C13 C14 -0.8(9) . . . . ?
C12 C13 C14 C15 0.6(8) . . . . ?
C9 N4 C15 C10 0.7(5) . . . . ?
C9 N4 C15 C14 177.7(5) . . . . ?
N3 C10 C15 N4 -0.1(5) . . . . ?
C11 C10 C15 N4 176.8(4) . . . . ?
N3 C10 C15 C14 -177.5(4) . . . . ?
C11 C10 C15 C14 -0.6(7) . . . . ?
C13 C14 C15 N4 -176.6(5) . . . . ?
C13 C14 C15 C10 0.1(7) . . . . ?
C23 N6 C17 N5 0.5(5) . . . . ?
C23 N6 C17 C16 177.9(4) . . . . ?
C18 N5 C17 N6 -0.4(5) . . . . ?
C18 N5 C17 C16 -177.9(4) . . . . ?
C24 C16 C17 N6 126.2(5) . . . . ?
C24 C16 C17 N5 -56.6(5) . . . . ?
C17 N5 C18 C23 0.1(5) . . . . ?
C17 N5 C18 C19 177.5(5) . . . . ?
N5 C18 C19 C20 -176.2(5) . . . . ?
C23 C18 C19 C20 0.8(7) . . . . ?
C18 C19 C20 C21 -0.1(8) . . . . ?
C19 C20 C21 C22 -0.6(8) . . . . ?
C20 C21 C22 C23 0.6(8) . . . . ?
N5 C18 C23 N6 0.1(5) . . . . ?
C19 C18 C23 N6 -177.5(4) . . . . ?
N5 C18 C23 C22 176.9(4) . . . . ?
C19 C18 C23 C22 -0.8(7) . . . . ?
C17 N6 C23 C18 -0.4(5) . . . . ?
C17 N6 C23 C22 -176.7(4) . . . . ?
C21 C22 C23 C18 0.1(7) . . . . ?
C21 C22 C23 N6 176.1(5) . . . . ?
C30 N8 C24 N7 0.2(5) . . . . ?
C30 N8 C24 C16 178.5(4) . . . . ?
C25 N7 C24 N8 0.4(6) . . . . ?
C25 N7 C24 C16 -177.9(4) . . . . ?
C17 C16 C24 N8 -91.8(5) . . . . ?
C17 C16 C24 N7 86.3(5) . . . . ?
C24 N7 C25 C30 -0.9(6) . . . . ?
C24 N7 C25 C26 -176.7(6) . . . . ?
C30 C25 C26 C27 6.7(10) . . . . ?
N7 C25 C26 C27 -178.0(6) . . . . ?
C25 C26 C27 C28 -8.6(11) . . . . ?
C26 C27 C28 C29 5.5(11) . . . . ?
C27 C28 C29 C30 0.2(10) . . . . ?
N7 C25 C30 C29 -177.5(5) . . . . ?
C26 C25 C30 C29 -1.4(9) . . . . ?
N7 C25 C30 N8 1.0(6) . . . . ?
C26 C25 C30 N8 177.2(5) . . . . ?
C28 C29 C30 C25 -2.4(9) . . . . ?
C28 C29 C30 N8 179.5(5) . . . . ?
C24 N8 C30 C25 -0.7(5) . . . . ?
C24 N8 C30 C29 177.6(6) . . . . ?
C38 N10 C32 N9 1.4(6) . . . . ?
C38 N10 C32 C31 -179.5(4) . . . . ?
C33 N9 C32 N10 -0.8(5) . . . . ?
C33 N9 C32 C31 -180.0(4) . . . . ?
C39 C31 C32 N10 -78.9(5) . . . . ?
C39 C31 C32 N9 100.1(5) . . . . ?
C32 N9 C33 C38 -0.1(5) . . . . ?
C32 N9 C33 C34 178.8(5) . . . . ?
N9 C33 C34 C35 -179.4(5) . . . . ?
C38 C33 C34 C35 -0.6(8) . . . . ?
C33 C34 C35 C36 -0.4(9) . . . . ?
C34 C35 C36 C37 5.5(11) . . . . ?
C35 C36 C37 C38 -9.2(11) . . . . ?
C36 C37 C38 N10 -178.7(6) . . . . ?
C36 C37 C38 C33 7.8(9) . . . . ?
C32 N10 C38 C37 -175.4(6) . . . . ?
C32 N10 C38 C33 -1.4(6) . . . . ?
N9 C33 C38 C37 176.0(5) . . . . ?
C34 C33 C38 C37 -3.0(8) . . . . ?
N9 C33 C38 N10 0.9(6) . . . . ?
C34 C33 C38 N10 -178.1(5) . . . . ?
C45 N12 C39 N11 -0.9(5) . . . . ?
C45 N12 C39 C31 176.4(4) . . . . ?
C40 N11 C39 N12 0.7(5) . . . . ?
C40 N11 C39 C31 -176.7(3) . . . . ?
C32 C31 C39 N12 50.9(5) . . . . ?
C32 C31 C39 N11 -132.1(4) . . . . ?
C39 N11 C40 C41 179.1(5) . . . . ?
C39 N11 C40 C45 -0.2(5) . . . . ?
N11 C40 C41 C42 -178.7(5) . . . . ?
C45 C40 C41 C42 0.5(7) . . . . ?
C40 C41 C42 C43 0.3(8) . . . . ?
C41 C42 C43 C44 -0.8(9) . . . . ?
C42 C43 C44 C45 0.5(8) . . . . ?
C43 C44 C45 N12 178.9(5) . . . . ?
C43 C44 C45 C40 0.3(7) . . . . ?
C39 N12 C45 C44 -178.0(5) . . . . ?
C39 N12 C45 C40 0.7(5) . . . . ?
N11 C40 C45 C44 178.6(4) . . . . ?
C41 C40 C45 C44 -0.8(7) . . . . ?
N11 C40 C45 N12 -0.4(5) . . . . ?
C41 C40 C45 N12 -179.7(4) . . . . ?
C53 N14 C47 N13 0.8(5) . . . . ?
C53 N14 C47 C46 -175.3(4) . . . . ?
C48 N13 C47 N14 -1.2(5) . . . . ?
C48 N13 C47 C46 175.0(4) . . . . ?
C54 C46 C47 N14 -127.1(4) . . . . ?
C54 C46 C47 N13 57.3(5) . . . . ?
C47 N13 C48 C49 -176.9(5) . . . . ?
C47 N13 C48 C53 1.0(4) . . . . ?
N13 C48 C49 C50 178.2(4) . . . . ?
C53 C48 C49 C50 0.6(7) . . . . ?
C48 C49 C50 C51 1.1(8) . . . . ?
C49 C50 C51 C52 -1.8(9) . . . . ?
C50 C51 C52 C53 0.9(8) . . . . ?
C51 C52 C53 N14 -178.1(5) . . . . ?
C51 C52 C53 C48 0.7(7) . . . . ?
C47 N14 C53 C52 178.8(5) . . . . ?
C47 N14 C53 C48 -0.1(5) . . . . ?
C49 C48 C53 C52 -1.5(7) . . . . ?
N13 C48 C53 C52 -179.7(4) . . . . ?
C49 C48 C53 N14 177.6(4) . . . . ?
N13 C48 C53 N14 -0.6(5) . . . . ?
C55 N15 C54 N16 1.5(6) . . . . ?
C55 N15 C54 C46 -178.7(4) . . . . ?
C60 N16 C54 N15 -1.0(5) . . . . ?
C60 N16 C54 C46 179.2(4) . . . . ?
C47 C46 C54 N15 -85.9(5) . . . . ?
C47 C46 C54 N16 93.9(5) . . . . ?
C54 N15 C55 C56 -175.8(6) . . . . ?
C54 N15 C55 C60 -1.3(6) . . . . ?
N15 C55 C56 C57 -179.2(7) . . . . ?
C60 C55 C56 C57 7.0(10) . . . . ?
C55 C56 C57 C58 -8.2(12) . . . . ?
C56 C57 C58 C59 4.9(12) . . . . ?
C57 C58 C59 C60 -0.2(10) . . . . ?
C54 N16 C60 C55 0.1(6) . . . . ?
C54 N16 C60 C59 178.9(5) . . . . ?
C56 C55 C60 N16 176.3(5) . . . . ?
N15 C55 C60 N16 0.7(6) . . . . ?
C56 C55 C60 C59 -2.7(8) . . . . ?
N15 C55 C60 C59 -178.2(4) . . . . ?
C58 C59 C60 N16 -179.4(5) . . . . ?
C58 C59 C60 C55 -0.7(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H3B N14 . . 1_455 2.811(5) 0.860 1.959 171.1 no
N3 H8A N16 . . 1_455 2.775(5) 0.860 1.958 158.1 no
N5 H15A N2 . . . 2.804(5) 0.860 1.969 163.6 no
N7 H20A N4 . . . 2.852(5) 0.860 2.051 154.8 no
N9 H27A N6 . . . 2.790(5) 0.860 1.945 167.2 no
N11 H32A N8 . . . 2.794(5) 0.860 1.983 156.7 no
N13 H39B N10 . . . 2.811(5) 0.860 1.972 165.0 no
N15 H44A N12 . . . 2.860(5) 0.860 2.078 150.9 no

# start Validation Reply Form
_vrf_PLAT110_BI2C-d2             
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ...          ? Check 
RESPONSE: Symmetry is actually broken by the hydrogen locations.
;
_vrf_PLAT111_BI2C-d2             
;
PROBLEM: ADDSYM Detects New (Pseudo) Centre of Symmetry .        100 %Fit  
RESPONSE: Symmetry is actually broken by the hydrogen locations.
;
_vrf_PLAT112_BI2C-d2             
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem         I        100 %Fit  
RESPONSE: Symmetry is actually broken by the hydrogen locations.
;
_vrf_PLAT113_BI2C-d2             
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group      I41/a Check 
RESPONSE: Symmetry is actually broken by the hydrogen locations and 
          confimed by the breaking of systematic absences.
;
# end Validation Reply Form
#==============================================================================
# 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
#==============================================================================
_chemical_name_systematic        
'N-deuterated bis-(1H-benzimidazol-2-yl)-methane'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol-d'
_exptl_crystal_preparation       'Dielectric properties'
####################################################################### 
# 
# 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_BI2C_LT
_database_code_depnum_ccdc_archive 'CCDC 1989815'
loop_
_audit_author_name
_audit_author_address
'Sachio Horiuchi'
;National Institute of Advanced Science and Technology 
Japan
;
_audit_update_record             
;
2020-03-11 deposited with the CCDC.	2020-05-13 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C15 H12 N4'
_chemical_formula_moiety         'C15 H12 N4'
_chemical_formula_weight         248.29
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      tetragonal
_space_group_name_H-M_alt        'P 41'
_space_group_name_Hall           'P 4w'
_space_group_IT_number           76
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,1/2+Z
3 -Y,+X,1/4+Z
4 +Y,-X,3/4+Z
#------------------------------------------------------------------------------
_cell_length_a                   18.2293(3)
_cell_length_b                   18.2293(3)
_cell_length_c                   15.6088(7)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     5186.9(3)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    22181
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      65.38
_cell_measurement_temperature    160
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2080.00
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku, ????)'
_exptl_absorpt_correction_T_min  0.857
_exptl_absorpt_correction_T_max  1.000

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

_diffrn_ambient_temperature      160
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     1.000
_diffrn_measurement_device_type  'IP DSC (Rigaku)'
_diffrn_reflns_number            33910
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_theta_max         65.380
_diffrn_reflns_theta_min         2.223
_diffrn_reflns_theta_full        36.870
_diffrn_measured_fraction_theta_max 0.743
_diffrn_measured_fraction_theta_full 0.932
_diffrn_reflns_Laue_measured_fraction_max 0.743
_diffrn_reflns_Laue_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.559
_diffrn_reflns_point_group_measured_fraction_full 0.825
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             18269
_reflns_number_gt                8131
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.467
_reflns_Friedel_fraction_max     0.366
_reflns_Friedel_fraction_full    0.710

#==============================================================================
# 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          0.1195
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_ref         0.2036
_refine_ls_wR_factor_gt          0.1749
_refine_ls_number_restraints     10
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         18269
_refine_ls_number_parameters     685
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0870P)²+0.3093P] 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          0.015
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 2143 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(10)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0074 0.0035
;
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 0.0135 0.0070
;
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 0.17023(19) 0.07691(18) 0.84551(19) 0.0304(7) Uani 1 1 d . . . . .
N2 N 0.1767(2) 0.19821(19) 0.8612(2) 0.0394(9) Uani 1 1 d . . . . .
N3 N 0.33781(19) 0.07254(18) 1.03167(19) 0.0309(7) Uani 1 1 d . . . . .
N4 N 0.33961(18) 0.18137(17) 0.96156(19) 0.0282(7) Uani 1 1 d . . . . .
N5 N 0.06819(18) 0.16172(19) 0.1475(2) 0.0333(7) Uani 1 1 d . . . . .
N6 N 0.17629(16) 0.16379(19) 0.2118(2) 0.0288(7) Uani 1 1 d . . . . .
N7 N 0.07282(18) 0.33310(18) 0.3321(2) 0.0304(7) Uani 1 1 d . . . . .
N8 N 0.19412(18) 0.3218(2) 0.3138(2) 0.0361(8) Uani 1 1 d . . . . .
N9 N 0.1598(2) 0.43162(19) 1.0302(2) 0.0343(7) Uani 1 1 d . . . . .
N10 N 0.16123(18) 0.32389(18) 0.9644(2) 0.0314(7) Uani 1 1 d . . . . .
N11 N 0.33251(18) 0.42756(17) 0.84568(19) 0.0296(7) Uani 1 1 d . . . . .
N12 N 0.3201(2) 0.30710(19) 0.8643(2) 0.0382(9) Uani 1 1 d . . . . .
N13 N 0.42768(18) 0.33917(19) 0.1466(2) 0.0324(7) Uani 1 1 d . . . . .
N14 N 0.31905(17) 0.34149(19) 0.2140(2) 0.0335(7) Uani 1 1 d . . . . .
N15 N 0.42322(19) 0.16900(17) 0.3297(2) 0.0308(7) Uani 1 1 d . . . . .
N16 N 0.30251(19) 0.1786(2) 0.3178(2) 0.0383(8) Uani 1 1 d . . . . .
C1 C 0.1869(2) 0.1324(2) 0.8973(2) 0.0263(7) Uani 1 1 d . . . . .
C2 C 0.1453(2) 0.1103(2) 0.7706(2) 0.0314(9) Uani 1 1 d . . . . .
C3 C 0.1202(2) 0.0775(2) 0.6930(2) 0.0350(8) Uani 1 1 d . . . . .
H3 H 0.118576 0.026797 0.686231 0.042 Uiso 1 1 calc R U . . .
C4 C 0.0984(3) 0.1240(2) 0.6290(3) 0.0537(13) Uani 1 1 d . . . . .
H4 H 0.078935 0.104669 0.578802 0.064 Uiso 1 1 calc R U . . .
C5 C 0.1050(3) 0.2006(3) 0.6377(3) 0.0571(15) Uani 1 1 d . . . . .
H5 H 0.091575 0.230560 0.592079 0.069 Uiso 1 1 calc R U . . .
C6 C 0.1312(3) 0.2328(3) 0.7127(3) 0.0527(13) Uani 1 1 d . . . . .
H6 H 0.135413 0.283359 0.718431 0.063 Uiso 1 1 calc R U . . .
C7 C 0.1510(3) 0.1843(2) 0.7796(2) 0.0355(9) Uani 1 1 d . . . . .
C8 C 0.2176(2) 0.1248(2) 0.9858(2) 0.0321(8) Uani 1 1 d . . . . .
H8A H 0.198627 0.164438 1.020730 0.039 Uiso 1 1 calc R U . . .
H8B H 0.199892 0.079119 1.010097 0.039 Uiso 1 1 calc R U . . .
C9 C 0.2983(2) 0.1254(2) 0.9914(2) 0.0261(7) Uani 1 1 d . . . . .
C10 C 0.4093(2) 0.0966(2) 1.0262(2) 0.0322(8) Uani 1 1 d . . . . .
C11 C 0.4744(2) 0.0653(2) 1.0596(3) 0.0378(10) Uani 1 1 d . . . . .
H11 H 0.474230 0.020332 1.087840 0.045 Uiso 1 1 calc R U . . .
C12 C 0.5379(2) 0.1049(3) 1.0481(3) 0.0396(10) Uani 1 1 d . . . . .
H12 H 0.581634 0.086023 1.069411 0.048 Uiso 1 1 calc R U . . .
C13 C 0.5394(3) 0.1721(2) 1.0058(3) 0.0392(10) Uani 1 1 d . . . . .
H13 H 0.583828 0.196730 0.999913 0.047 Uiso 1 1 calc R U . . .
C14 C 0.4768(2) 0.2028(2) 0.9726(3) 0.0368(9) Uani 1 1 d . . . . .
H14 H 0.478195 0.247303 0.943541 0.044 Uiso 1 1 calc R U . . .
C15 C 0.4116(2) 0.1655(2) 0.9838(2) 0.0274(8) Uani 1 1 d . . . . .
C16 C 0.1191(2) 0.2027(2) 0.1849(2) 0.0285(8) Uani 1 1 d . . . . .
C17 C 0.0924(2) 0.0890(2) 0.1488(2) 0.0322(9) Uani 1 1 d . . . . .
C18 C 0.0630(2) 0.0254(3) 0.1181(3) 0.0428(11) Uani 1 1 d . . . . .
H18 H 0.017667 0.025238 0.090644 0.051 Uiso 1 1 calc R U . . .
C19 C 0.1023(3) -0.0387(3) 0.1289(3) 0.0433(11) Uani 1 1 d . . . . .
H19 H 0.083206 -0.082883 0.109125 0.052 Uiso 1 1 calc R U . . .
C20 C 0.1704(2) -0.0376(2) 0.1690(3) 0.0393(10) Uani 1 1 d . . . . .
H20 H 0.196162 -0.081340 0.174528 0.047 Uiso 1 1 calc R U . . .
C21 C 0.2015(2) 0.0262(2) 0.2012(3) 0.0337(9) Uani 1 1 d . . . . .
H21 H 0.246760 0.026213 0.228686 0.040 Uiso 1 1 calc R U . . .
C22 C 0.1599(2) 0.0915(2) 0.1897(2) 0.0280(8) Uani 1 1 d . . . . .
C23 C 0.1137(2) 0.2845(2) 0.1907(2) 0.0335(8) Uani 1 1 d . . . . .
H23A H 0.065256 0.299619 0.172079 0.040 Uiso 1 1 calc R U . . .
H23B H 0.149188 0.306160 0.151826 0.040 Uiso 1 1 calc R U . . .
C24 C 0.1272(2) 0.3136(2) 0.2794(2) 0.0278(8) Uani 1 1 d . . . . .
C25 C 0.1032(2) 0.3557(2) 0.4077(2) 0.0276(8) Uani 1 1 d . . . . .
C26 C 0.0746(2) 0.3831(3) 0.4818(3) 0.0406(10) Uani 1 1 d . . . . .
H26 H 0.024481 0.390797 0.488045 0.049 Uiso 1 1 calc R U . . .
C27 C 0.1240(2) 0.3994(3) 0.5486(2) 0.0422(10) Uani 1 1 d . . . . .
H27 H 0.106147 0.415106 0.601339 0.051 Uiso 1 1 calc R U . . .
C28 C 0.1984(3) 0.3923(3) 0.5366(3) 0.0579(14) Uani 1 1 d . . . . .
H28 H 0.229818 0.403976 0.581534 0.070 Uiso 1 1 calc R U . . .
C29 C 0.2279(3) 0.3686(3) 0.4608(4) 0.0635(15) Uani 1 1 d . . . . .
H29 H 0.278389 0.365623 0.453419 0.076 Uiso 1 1 calc R U . . .
C30 C 0.1806(2) 0.3493(3) 0.3960(3) 0.0366(10) Uani 1 1 d . . . . .
C31 C 0.2009(2) 0.3798(2) 0.9925(2) 0.0319(9) Uani 1 1 d . . . . .
C32 C 0.0885(2) 0.4078(2) 1.0267(2) 0.0316(8) Uani 1 1 d . . . . .
C33 C 0.0224(2) 0.4389(2) 1.0584(3) 0.0366(9) Uani 1 1 d . . . . .
H33 H 0.021866 0.484510 1.084980 0.044 Uiso 1 1 calc R U . . .
C34 C -0.0414(2) 0.3979(3) 1.0479(3) 0.0421(11) Uani 1 1 d . . . . .
H34 H -0.085848 0.416466 1.067727 0.050 Uiso 1 1 calc R U . . .
C35 C -0.0396(3) 0.3286(3) 1.0075(3) 0.0455(12) Uani 1 1 d . . . . .
H35 H -0.082870 0.302249 1.000972 0.055 Uiso 1 1 calc R U . . .
C36 C 0.0254(3) 0.2994(2) 0.9776(3) 0.0396(10) Uani 1 1 d . . . . .
H36 H 0.026182 0.253142 0.952440 0.048 Uiso 1 1 calc R U . . .
C37 C 0.0894(3) 0.3399(2) 0.9854(2) 0.0344(9) Uani 1 1 d . . . . .
C38 C 0.2827(2) 0.3859(2) 0.9871(3) 0.0358(9) Uani 1 1 d . . . . .
H38A H 0.304570 0.350656 1.026032 0.043 Uiso 1 1 calc R U . . .
H38B H 0.297325 0.434517 1.005694 0.043 Uiso 1 1 calc R U . . .
C39 C 0.3122(2) 0.3726(2) 0.8982(2) 0.0283(8) Uani 1 1 d . . . . .
C40 C 0.3561(2) 0.3945(2) 0.7709(2) 0.0310(8) Uani 1 1 d . . . . .
C41 C 0.3820(2) 0.4257(2) 0.6925(2) 0.0386(9) Uani 1 1 d . . . . .
H41A H 0.384931 0.476146 0.684024 0.046 Uiso 1 1 calc R U . . .
C42 C 0.4016(3) 0.3773(2) 0.6320(3) 0.0492(12) Uani 1 1 d . . . . .
H42A H 0.422455 0.395151 0.581792 0.059 Uiso 1 1 calc R U . . .
C43 C 0.3923(3) 0.3006(3) 0.6404(4) 0.0615(16) Uani 1 1 d . . . . .
H43A H 0.404487 0.270157 0.594777 0.074 Uiso 1 1 calc R U . . .
C44 C 0.3656(3) 0.2705(2) 0.7145(3) 0.0482(11) Uani 1 1 d . . . . .
H44A H 0.359334 0.220135 0.721009 0.058 Uiso 1 1 calc R U . . .
C45 C 0.3478(2) 0.3213(2) 0.7815(3) 0.0365(9) Uani 1 1 d . . . . .
C46 C 0.3768(2) 0.3000(2) 0.1850(2) 0.0282(8) Uani 1 1 d . . . . .
C47 C 0.4038(2) 0.4119(2) 0.1509(2) 0.0308(8) Uani 1 1 d . . . . .
C48 C 0.4349(3) 0.4743(3) 0.1190(3) 0.0448(11) Uani 1 1 d . . . . .
H48A H 0.479839 0.473046 0.090899 0.054 Uiso 1 1 calc R U . . .
C49 C 0.3973(3) 0.5390(3) 0.1299(3) 0.0464(12) Uani 1 1 d . . . . .
H49 H 0.417381 0.582288 0.108672 0.056 Uiso 1 1 calc R U . . .
C50 C 0.3298(3) 0.5414(2) 0.1720(3) 0.0418(11) Uani 1 1 d . . . . .
H50 H 0.305981 0.586204 0.177895 0.050 Uiso 1 1 calc R U . . .
C51 C 0.2969(2) 0.4779(2) 0.2057(3) 0.0390(10) Uani 1 1 d . . . . .
H51 H 0.252142 0.478876 0.234336 0.047 Uiso 1 1 calc R U . . .
C52 C 0.3366(2) 0.4130(2) 0.1929(2) 0.0289(8) Uani 1 1 d . . . . .
C53 C 0.3786(3) 0.2164(2) 0.1915(2) 0.0381(9) Uani 1 1 d . . . . .
H53A H 0.340621 0.196246 0.154826 0.046 Uiso 1 1 calc R U . . .
H53B H 0.425477 0.198909 0.170507 0.046 Uiso 1 1 calc R U . . .
C54 C 0.3675(2) 0.1891(2) 0.2797(2) 0.0292(8) Uani 1 1 d . . . . .
C55 C 0.3906(2) 0.1455(2) 0.4065(2) 0.0299(8) Uani 1 1 d . . . . .
C56 C 0.4219(2) 0.1184(2) 0.4791(3) 0.0394(9) Uani 1 1 d . . . . .
H56 H 0.472442 0.112443 0.483372 0.047 Uiso 1 1 calc R U . . .
C57 C 0.3749(3) 0.0995(3) 0.5479(3) 0.0477(12) Uani 1 1 d . . . . .
H57 H 0.394599 0.082576 0.599200 0.057 Uiso 1 1 calc R U . . .
C58 C 0.3002(3) 0.1060(3) 0.5390(3) 0.0622(15) Uani 1 1 d . . . . .
H58 H 0.269715 0.092771 0.584217 0.075 Uiso 1 1 calc R U . . .
C59 C 0.2693(3) 0.1322(3) 0.4634(4) 0.0676(17) Uani 1 1 d . . . . .
H59 H 0.218691 0.136012 0.457786 0.081 Uiso 1 1 calc R U . . .
C60 C 0.3135(2) 0.1517(3) 0.3991(3) 0.0361(9) Uani 1 1 d . . . . .
H41 H 0.170000 0.243000 0.892000 0.071 Uiso 1 1 d . U . . .
H42 H 0.324000 0.228001 0.910000 0.066 Uiso 1 1 d . U . . .
H43 H 0.030000 0.184000 0.117001 0.090 Uiso 1 1 d . U . . .
H44 H 0.011001 0.331000 0.318001 0.034 Uiso 1 1 d . U . . .
H45 H 0.167001 0.491000 1.047001 0.042 Uiso 1 1 d . U . . .
H46 H 0.332000 0.474999 0.857000 0.046 Uiso 1 1 d . U . . .
H47 H 0.288000 0.322400 0.242000 0.080 Uiso 1 1 d . U . . .
H48 H 0.265000 0.195001 0.282000 0.056 Uiso 1 1 d . U . . .


#==============================================================================
_computing_data_collection       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL Version 2018/3 (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 1.330(5) . ?
N1 C2 1.395(5) . ?
N2 C1 1.338(5) . ?
N2 C7 1.380(5) . ?
N2 H41 0.9551 . ?
N3 C9 1.358(5) . ?
N3 C10 1.377(5) . ?
N4 C9 1.350(4) . ?
N4 C15 1.388(5) . ?
N4 H42 1.2047 . ?
N5 C16 1.327(5) . ?
N5 C17 1.398(5) . ?
N5 H43 0.9363 . ?
N6 C16 1.329(4) . ?
N6 C22 1.395(5) . ?
N7 C24 1.336(5) . ?
N7 C25 1.366(5) . ?
N7 H44 1.1488 . ?
N8 C24 1.341(5) . ?
N8 C30 1.400(5) . ?
N9 C31 1.341(5) . ?
N9 C32 1.373(5) . ?
N9 H45 1.1214 . ?
N10 C31 1.325(5) . ?
N10 C37 1.382(5) . ?
N11 C39 1.346(5) . ?
N11 C40 1.382(5) . ?
N11 H46 0.8827 . ?
N12 C39 1.314(5) . ?
N12 C45 1.411(5) . ?
N13 C46 1.315(5) . ?
N13 C47 1.398(5) . ?
N14 C46 1.374(5) . ?
N14 C52 1.382(5) . ?
N14 H47 0.7950 . ?
N15 C54 1.333(5) . ?
N15 C55 1.404(5) . ?
N16 C54 1.339(5) . ?
N16 C60 1.377(5) . ?
N16 H48 0.9320 . ?
C1 C8 1.497(5) . ?
C2 C7 1.359(6) . ?
C2 C3 1.427(5) . ?
C3 C4 1.369(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.408(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.416(5) . ?
C6 H6 0.9300 . ?
C8 C9 1.474(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C10 C11 1.417(5) . ?
C10 C15 1.420(5) . ?
C11 C12 1.377(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.391(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.374(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.380(6) . ?
C14 H14 0.9300 . ?
C16 C23 1.497(6) . ?
C17 C18 1.365(6) . ?
C17 C22 1.386(5) . ?
C18 C19 1.382(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.390(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.387(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.423(6) . ?
C21 H21 0.9300 . ?
C23 C24 1.503(5) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C25 C26 1.364(5) . ?
C25 C30 1.427(5) . ?
C26 C27 1.409(6) . ?
C26 H26 0.9300 . ?
C27 C28 1.375(7) . ?
C27 H27 0.9300 . ?
C28 C29 1.369(7) . ?
C28 H28 0.9300 . ?
C29 C30 1.375(6) . ?
C29 H29 0.9300 . ?
C31 C38 1.498(6) . ?
C32 C37 1.394(5) . ?
C32 C33 1.420(6) . ?
C33 C34 1.392(6) . ?
C33 H33 0.9300 . ?
C34 C35 1.412(7) . ?
C34 H34 0.9300 . ?
C35 C36 1.380(6) . ?
C35 H35 0.9300 . ?
C36 C37 1.387(6) . ?
C36 H36 0.9300 . ?
C38 C39 1.507(5) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C40 C45 1.352(6) . ?
C40 C41 1.430(5) . ?
C41 C42 1.341(6) . ?
C41 H41A 0.9300 . ?
C42 C43 1.414(6) . ?
C42 H42A 0.9300 . ?
C43 C44 1.371(6) . ?
C43 H43A 0.9300 . ?
C44 C45 1.435(6) . ?
C44 H44A 0.9300 . ?
C46 C53 1.527(6) . ?
C47 C48 1.364(6) . ?
C47 C52 1.389(5) . ?
C48 C49 1.375(7) . ?
C48 H48A 0.9300 . ?
C49 C50 1.395(7) . ?
C49 H49 0.9300 . ?
C50 C51 1.407(6) . ?
C50 H50 0.9300 . ?
C51 C52 1.401(6) . ?
C51 H51 0.9300 . ?
C53 C54 1.478(5) . ?
C53 H53A 0.9700 . ?
C53 H53B 0.9700 . ?
C55 C56 1.362(5) . ?
C55 C60 1.414(5) . ?
C56 C57 1.417(6) . ?
C56 H56 0.9300 . ?
C57 C58 1.374(7) . ?
C57 H57 0.9300 . ?
C58 C59 1.390(7) . ?
C58 H58 0.9300 . ?
C59 C60 1.335(7) . ?
C59 H59 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
C1 N1 C2 104.6(3) . . ?
C1 N2 C7 105.7(3) . . ?
C1 N2 H41 124.9 . . ?
C7 N2 H41 125.3 . . ?
C9 N3 C10 104.3(3) . . ?
C9 N4 C15 106.5(3) . . ?
C9 N4 H42 129.2 . . ?
C15 N4 H42 122.5 . . ?
C16 N5 C17 107.8(3) . . ?
C16 N5 H43 120.0 . . ?
C17 N5 H43 130.9 . . ?
C16 N6 C22 105.0(3) . . ?
C24 N7 C25 108.1(3) . . ?
C24 N7 H44 126.9 . . ?
C25 N7 H44 125.0 . . ?
C24 N8 C30 104.3(3) . . ?
C31 N9 C32 106.8(3) . . ?
C31 N9 H45 135.8 . . ?
C32 N9 H45 115.2 . . ?
C31 N10 C37 106.0(3) . . ?
C39 N11 C40 106.0(3) . . ?
C39 N11 H46 127.1 . . ?
C40 N11 H46 126.8 . . ?
C39 N12 C45 103.9(3) . . ?
C46 N13 C47 105.9(3) . . ?
C46 N14 C52 105.3(3) . . ?
C46 N14 H47 119.0 . . ?
C52 N14 H47 135.1 . . ?
C54 N15 C55 105.1(3) . . ?
C54 N16 C60 109.4(4) . . ?
C54 N16 H48 109.7 . . ?
C60 N16 H48 140.7 . . ?
N1 C1 N2 113.2(3) . . ?
N1 C1 C8 125.1(3) . . ?
N2 C1 C8 121.6(3) . . ?
C7 C2 N1 108.7(3) . . ?
C7 C2 C3 122.0(4) . . ?
N1 C2 C3 129.2(4) . . ?
C4 C3 C2 116.8(4) . . ?
C4 C3 H3 121.6 . . ?
C2 C3 H3 121.6 . . ?
C3 C4 C5 121.3(4) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 121.8(4) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C7 116.4(4) . . ?
C5 C6 H6 121.8 . . ?
C7 C6 H6 121.8 . . ?
C2 C7 N2 107.7(4) . . ?
C2 C7 C6 121.5(4) . . ?
N2 C7 C6 130.8(4) . . ?
C9 C8 C1 115.3(3) . . ?
C9 C8 H8A 108.4 . . ?
C1 C8 H8A 108.4 . . ?
C9 C8 H8B 108.4 . . ?
C1 C8 H8B 108.4 . . ?
H8A C8 H8B 107.5 . . ?
N4 C9 N3 113.6(3) . . ?
N4 C9 C8 122.9(3) . . ?
N3 C9 C8 123.4(3) . . ?
N3 C10 C11 129.9(4) . . ?
N3 C10 C15 109.8(3) . . ?
C11 C10 C15 120.2(4) . . ?
C12 C11 C10 116.4(4) . . ?
C12 C11 H11 121.8 . . ?
C10 C11 H11 121.8 . . ?
C11 C12 C13 122.8(4) . . ?
C11 C12 H12 118.6 . . ?
C13 C12 H12 118.6 . . ?
C14 C13 C12 121.4(4) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 117.9(4) . . ?
C13 C14 H14 121.1 . . ?
C15 C14 H14 121.1 . . ?
C14 C15 N4 132.8(4) . . ?
C14 C15 C10 121.4(4) . . ?
N4 C15 C10 105.8(3) . . ?
N5 C16 N6 112.8(3) . . ?
N5 C16 C23 122.8(3) . . ?
N6 C16 C23 124.3(4) . . ?
C18 C17 C22 122.6(4) . . ?
C18 C17 N5 132.5(4) . . ?
C22 C17 N5 104.9(4) . . ?
C17 C18 C19 118.1(4) . . ?
C17 C18 H18 121.0 . . ?
C19 C18 H18 121.0 . . ?
C18 C19 C20 120.4(4) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C21 C20 C19 122.7(4) . . ?
C21 C20 H20 118.6 . . ?
C19 C20 H20 118.6 . . ?
C20 C21 C22 115.9(4) . . ?
C20 C21 H21 122.0 . . ?
C22 C21 H21 122.0 . . ?
C17 C22 N6 109.5(3) . . ?
C17 C22 C21 120.2(4) . . ?
N6 C22 C21 130.2(4) . . ?
C16 C23 C24 113.3(3) . . ?
C16 C23 H23A 108.9 . . ?
C24 C23 H23A 108.9 . . ?
C16 C23 H23B 108.9 . . ?
C24 C23 H23B 108.9 . . ?
H23A C23 H23B 107.7 . . ?
N7 C24 N8 113.5(3) . . ?
N7 C24 C23 122.7(3) . . ?
N8 C24 C23 123.8(4) . . ?
C26 C25 N7 133.5(4) . . ?
C26 C25 C30 121.0(4) . . ?
N7 C25 C30 105.4(3) . . ?
C25 C26 C27 117.5(4) . . ?
C25 C26 H26 121.3 . . ?
C27 C26 H26 121.3 . . ?
C28 C27 C26 120.6(4) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C29 C28 C27 122.3(5) . . ?
C29 C28 H28 118.8 . . ?
C27 C28 H28 118.8 . . ?
C28 C29 C30 118.1(5) . . ?
C28 C29 H29 121.0 . . ?
C30 C29 H29 121.0 . . ?
C29 C30 N8 131.0(4) . . ?
C29 C30 C25 120.3(4) . . ?
N8 C30 C25 108.7(4) . . ?
N10 C31 N9 112.5(4) . . ?
N10 C31 C38 125.6(4) . . ?
N9 C31 C38 121.9(4) . . ?
N9 C32 C37 106.8(4) . . ?
N9 C32 C33 131.5(4) . . ?
C37 C32 C33 121.7(4) . . ?
C34 C33 C32 117.0(4) . . ?
C34 C33 H33 121.5 . . ?
C32 C33 H33 121.5 . . ?
C33 C34 C35 120.8(4) . . ?
C33 C34 H34 119.6 . . ?
C35 C34 H34 119.6 . . ?
C36 C35 C34 121.2(4) . . ?
C36 C35 H35 119.4 . . ?
C34 C35 H35 119.4 . . ?
C35 C36 C37 119.1(4) . . ?
C35 C36 H36 120.5 . . ?
C37 C36 H36 120.5 . . ?
N10 C37 C36 131.6(4) . . ?
N10 C37 C32 108.0(4) . . ?
C36 C37 C32 120.2(4) . . ?
C31 C38 C39 113.3(3) . . ?
C31 C38 H38A 108.9 . . ?
C39 C38 H38A 108.9 . . ?
C31 C38 H38B 108.9 . . ?
C39 C38 H38B 108.9 . . ?
H38A C38 H38B 107.7 . . ?
N12 C39 N11 113.6(3) . . ?
N12 C39 C38 123.7(4) . . ?
N11 C39 C38 122.6(4) . . ?
C45 C40 N11 107.0(3) . . ?
C45 C40 C41 122.3(4) . . ?
N11 C40 C41 130.7(4) . . ?
C42 C41 C40 115.4(4) . . ?
C42 C41 H41A 122.3 . . ?
C40 C41 H41A 122.3 . . ?
C41 C42 C43 123.6(4) . . ?
C41 C42 H42A 118.2 . . ?
C43 C42 H42A 118.2 . . ?
C44 C43 C42 121.1(4) . . ?
C44 C43 H43A 119.4 . . ?
C42 C43 H43A 119.4 . . ?
C43 C44 C45 115.9(4) . . ?
C43 C44 H44A 122.1 . . ?
C45 C44 H44A 122.1 . . ?
C40 C45 N12 109.5(4) . . ?
C40 C45 C44 121.5(4) . . ?
N12 C45 C44 129.0(4) . . ?
N13 C46 N14 113.0(3) . . ?
N13 C46 C53 123.9(3) . . ?
N14 C46 C53 122.9(4) . . ?
C48 C47 C52 121.8(4) . . ?
C48 C47 N13 130.1(4) . . ?
C52 C47 N13 108.1(4) . . ?
C47 C48 C49 117.6(4) . . ?
C47 C48 H48A 121.2 . . ?
C49 C48 H48A 121.2 . . ?
C48 C49 C50 121.6(4) . . ?
C48 C49 H49 119.2 . . ?
C50 C49 H49 119.2 . . ?
C49 C50 C51 121.8(4) . . ?
C49 C50 H50 119.1 . . ?
C51 C50 H50 119.1 . . ?
C52 C51 C50 114.9(4) . . ?
C52 C51 H51 122.6 . . ?
C50 C51 H51 122.6 . . ?
N14 C52 C47 107.6(3) . . ?
N14 C52 C51 130.0(4) . . ?
C47 C52 C51 122.3(4) . . ?
C54 C53 C46 113.3(3) . . ?
C54 C53 H53A 108.9 . . ?
C46 C53 H53A 108.9 . . ?
C54 C53 H53B 108.9 . . ?
C46 C53 H53B 108.9 . . ?
H53A C53 H53B 107.7 . . ?
N15 C54 N16 112.0(3) . . ?
N15 C54 C53 122.3(4) . . ?
N16 C54 C53 125.7(4) . . ?
C56 C55 N15 130.0(4) . . ?
C56 C55 C60 120.8(4) . . ?
N15 C55 C60 109.1(3) . . ?
C55 C56 C57 117.8(4) . . ?
C55 C56 H56 121.1 . . ?
C57 C56 H56 121.1 . . ?
C58 C57 C56 120.1(4) . . ?
C58 C57 H57 119.9 . . ?
C56 C57 H57 119.9 . . ?
C57 C58 C59 121.1(5) . . ?
C57 C58 H58 119.5 . . ?
C59 C58 H58 119.5 . . ?
C60 C59 C58 119.0(4) . . ?
C60 C59 H59 120.5 . . ?
C58 C59 H59 120.5 . . ?
C59 C60 N16 134.5(4) . . ?
C59 C60 C55 121.2(4) . . ?
N16 C60 C55 104.3(4) . . ?

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
C2 N1 C1 N2 -1.7(5) . . . . ?
C2 N1 C1 C8 -178.8(4) . . . . ?
C7 N2 C1 N1 0.3(5) . . . . ?
C7 N2 C1 C8 177.5(4) . . . . ?
C1 N1 C2 C7 2.5(5) . . . . ?
C1 N1 C2 C3 179.9(4) . . . . ?
C7 C2 C3 C4 -3.1(7) . . . . ?
N1 C2 C3 C4 179.8(4) . . . . ?
C2 C3 C4 C5 3.8(8) . . . . ?
C3 C4 C5 C6 -2.5(9) . . . . ?
C4 C5 C6 C7 0.2(9) . . . . ?
N1 C2 C7 N2 -2.4(5) . . . . ?
C3 C2 C7 N2 -180.0(4) . . . . ?
N1 C2 C7 C6 178.6(4) . . . . ?
C3 C2 C7 C6 0.9(8) . . . . ?
C1 N2 C7 C2 1.3(5) . . . . ?
C1 N2 C7 C6 -179.8(5) . . . . ?
C5 C6 C7 C2 0.5(8) . . . . ?
C5 C6 C7 N2 -178.3(5) . . . . ?
N1 C1 C8 C9 91.9(5) . . . . ?
N2 C1 C8 C9 -84.9(5) . . . . ?
C15 N4 C9 N3 -0.5(4) . . . . ?
C15 N4 C9 C8 175.5(3) . . . . ?
C10 N3 C9 N4 -0.6(4) . . . . ?
C10 N3 C9 C8 -176.5(3) . . . . ?
C1 C8 C9 N4 57.2(5) . . . . ?
C1 C8 C9 N3 -127.2(4) . . . . ?
C9 N3 C10 C11 177.4(4) . . . . ?
C9 N3 C10 C15 1.4(4) . . . . ?
N3 C10 C11 C12 -176.0(4) . . . . ?
C15 C10 C11 C12 -0.3(6) . . . . ?
C10 C11 C12 C13 -0.2(6) . . . . ?
C11 C12 C13 C14 -0.2(7) . . . . ?
C12 C13 C14 C15 1.1(6) . . . . ?
C13 C14 C15 N4 177.6(4) . . . . ?
C13 C14 C15 C10 -1.6(6) . . . . ?
C9 N4 C15 C14 -178.0(4) . . . . ?
C9 N4 C15 C10 1.3(4) . . . . ?
N3 C10 C15 C14 177.7(3) . . . . ?
C11 C10 C15 C14 1.2(6) . . . . ?
N3 C10 C15 N4 -1.7(4) . . . . ?
C11 C10 C15 N4 -178.2(3) . . . . ?
C17 N5 C16 N6 0.0(4) . . . . ?
C17 N5 C16 C23 176.4(3) . . . . ?
C22 N6 C16 N5 -0.3(4) . . . . ?
C22 N6 C16 C23 -176.7(3) . . . . ?
C16 N5 C17 C18 -178.4(4) . . . . ?
C16 N5 C17 C22 0.4(4) . . . . ?
C22 C17 C18 C19 0.3(6) . . . . ?
N5 C17 C18 C19 178.9(4) . . . . ?
C17 C18 C19 C20 -0.8(7) . . . . ?
C18 C19 C20 C21 1.2(7) . . . . ?
C19 C20 C21 C22 -0.9(6) . . . . ?
C18 C17 C22 N6 178.4(4) . . . . ?
N5 C17 C22 N6 -0.5(4) . . . . ?
C18 C17 C22 C21 -0.1(6) . . . . ?
N5 C17 C22 C21 -179.0(3) . . . . ?
C16 N6 C22 C17 0.5(4) . . . . ?
C16 N6 C22 C21 178.8(4) . . . . ?
C20 C21 C22 C17 0.3(6) . . . . ?
C20 C21 C22 N6 -177.8(4) . . . . ?
N5 C16 C23 C24 130.7(4) . . . . ?
N6 C16 C23 C24 -53.2(5) . . . . ?
C25 N7 C24 N8 -0.5(5) . . . . ?
C25 N7 C24 C23 178.9(4) . . . . ?
C30 N8 C24 N7 -0.1(5) . . . . ?
C30 N8 C24 C23 -179.5(4) . . . . ?
C16 C23 C24 N7 -100.2(4) . . . . ?
C16 C23 C24 N8 79.1(5) . . . . ?
C24 N7 C25 C26 177.7(5) . . . . ?
C24 N7 C25 C30 0.9(5) . . . . ?
N7 C25 C26 C27 178.7(4) . . . . ?
C30 C25 C26 C27 -4.9(7) . . . . ?
C25 C26 C27 C28 4.3(8) . . . . ?
C26 C27 C28 C29 -0.8(9) . . . . ?
C27 C28 C29 C30 -2.0(9) . . . . ?
C28 C29 C30 N8 -178.1(5) . . . . ?
C28 C29 C30 C25 1.4(8) . . . . ?
C24 N8 C30 C29 -179.8(6) . . . . ?
C24 N8 C30 C25 0.7(5) . . . . ?
C26 C25 C30 C29 2.2(7) . . . . ?
N7 C25 C30 C29 179.4(5) . . . . ?
C26 C25 C30 N8 -178.2(4) . . . . ?
N7 C25 C30 N8 -1.0(5) . . . . ?
C37 N10 C31 N9 -0.3(4) . . . . ?
C37 N10 C31 C38 177.7(4) . . . . ?
C32 N9 C31 N10 0.3(4) . . . . ?
C32 N9 C31 C38 -177.9(3) . . . . ?
C31 N9 C32 C37 0.0(4) . . . . ?
C31 N9 C32 C33 177.9(4) . . . . ?
N9 C32 C33 C34 -176.6(4) . . . . ?
C37 C32 C33 C34 1.2(6) . . . . ?
C32 C33 C34 C35 0.1(6) . . . . ?
C33 C34 C35 C36 0.2(6) . . . . ?
C34 C35 C36 C37 -1.7(6) . . . . ?
C31 N10 C37 C36 -174.6(4) . . . . ?
C31 N10 C37 C32 0.3(4) . . . . ?
C35 C36 C37 N10 177.4(4) . . . . ?
C35 C36 C37 C32 3.0(6) . . . . ?
N9 C32 C37 N10 -0.2(4) . . . . ?
C33 C32 C37 N10 -178.4(3) . . . . ?
N9 C32 C37 C36 175.5(4) . . . . ?
C33 C32 C37 C36 -2.8(6) . . . . ?
N10 C31 C38 C39 51.6(6) . . . . ?
N9 C31 C38 C39 -130.5(4) . . . . ?
C45 N12 C39 N11 -0.5(5) . . . . ?
C45 N12 C39 C38 179.1(4) . . . . ?
C40 N11 C39 N12 -0.3(5) . . . . ?
C40 N11 C39 C38 -179.9(4) . . . . ?
C31 C38 C39 N12 -78.3(5) . . . . ?
C31 C38 C39 N11 101.2(5) . . . . ?
C39 N11 C40 C45 1.0(5) . . . . ?
C39 N11 C40 C41 178.1(4) . . . . ?
C45 C40 C41 C42 -3.9(7) . . . . ?
N11 C40 C41 C42 179.3(4) . . . . ?
C40 C41 C42 C43 5.2(8) . . . . ?
C41 C42 C43 C44 -3.6(10) . . . . ?
C42 C43 C44 C45 0.3(9) . . . . ?
N11 C40 C45 N12 -1.3(5) . . . . ?
C41 C40 C45 N12 -178.7(4) . . . . ?
N11 C40 C45 C44 178.4(4) . . . . ?
C41 C40 C45 C44 1.0(7) . . . . ?
C39 N12 C45 C40 1.1(5) . . . . ?
C39 N12 C45 C44 -178.6(5) . . . . ?
C43 C44 C45 C40 0.9(8) . . . . ?
C43 C44 C45 N12 -179.5(5) . . . . ?
C47 N13 C46 N14 1.0(4) . . . . ?
C47 N13 C46 C53 177.0(3) . . . . ?
C52 N14 C46 N13 -1.2(4) . . . . ?
C52 N14 C46 C53 -177.2(3) . . . . ?
C46 N13 C47 C48 -178.0(4) . . . . ?
C46 N13 C47 C52 -0.4(4) . . . . ?
C52 C47 C48 C49 0.1(6) . . . . ?
N13 C47 C48 C49 177.4(4) . . . . ?
C47 C48 C49 C50 0.0(7) . . . . ?
C48 C49 C50 C51 0.3(7) . . . . ?
C49 C50 C51 C52 -0.6(6) . . . . ?
C46 N14 C52 C47 0.8(4) . . . . ?
C46 N14 C52 C51 178.6(4) . . . . ?
C48 C47 C52 N14 177.5(4) . . . . ?
N13 C47 C52 N14 -0.3(4) . . . . ?
C48 C47 C52 C51 -0.4(6) . . . . ?
N13 C47 C52 C51 -178.2(4) . . . . ?
C50 C51 C52 N14 -176.8(4) . . . . ?
C50 C51 C52 C47 0.7(6) . . . . ?
N13 C46 C53 C54 129.4(4) . . . . ?
N14 C46 C53 C54 -55.1(5) . . . . ?
C55 N15 C54 N16 -1.4(5) . . . . ?
C55 N15 C54 C53 -179.0(4) . . . . ?
C60 N16 C54 N15 1.6(5) . . . . ?
C60 N16 C54 C53 179.1(4) . . . . ?
C46 C53 C54 N15 -98.7(5) . . . . ?
C46 C53 C54 N16 84.1(5) . . . . ?
C54 N15 C55 C56 179.0(5) . . . . ?
C54 N15 C55 C60 0.7(5) . . . . ?
N15 C55 C56 C57 179.4(4) . . . . ?
C60 C55 C56 C57 -2.5(7) . . . . ?
C55 C56 C57 C58 2.5(8) . . . . ?
C56 C57 C58 C59 -1.0(9) . . . . ?
C57 C58 C59 C60 -0.6(10) . . . . ?
C58 C59 C60 N16 179.6(5) . . . . ?
C58 C59 C60 C55 0.6(9) . . . . ?
C54 N16 C60 C59 179.8(6) . . . . ?
C54 N16 C60 C55 -1.0(5) . . . . ?
C56 C55 C60 C59 1.0(8) . . . . ?
N15 C55 C60 C59 179.5(5) . . . . ?
C56 C55 C60 N16 -178.3(4) . . . . ?
N15 C55 C60 N16 0.2(5) . . . . ?


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

# start Validation Reply Form
_vrf_PLAT029_BI2C_LT             
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.932 Why?  
RESPONSE:
The data have been collected on 1-circle goniometer with IP area detector 
diffractometer. It is only the very high angle data that is incomplete due to 
the shape of the area detector, and we have ca. 100% coverage in the low angle 
data. This will always be a problem with area detector data that is not 
truncated. In addition, changing the direction of crystal is difficult 
due to the N2 blower for the temperaature control. The obtained 
analysis was sufficient to elucidate the molecular structure. 
;
_vrf_PLAT353_BI2C_LT             
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N4       - H42      .       1.20 Ang.  
RESPONSE: 
Due to the N-H...N hydrogen bond.
;
_vrf_PLAT110_BI2C_LT             
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ...          ? Check 
RESPONSE: 
The crystal has pseudo symmetry of higher symmetric space group (I41/a).  
However, we checked the reflections carefully and confirmed the breaking 
of the extinction rule of I41/a clearly.
;
_vrf_PLAT111_BI2C_LT             
;
PROBLEM: ADDSYM Detects New (Pseudo) Centre of Symmetry .        100 %Fit  
RESPONSE: 
The crystal has pseudo symmetry of higher symmetric space group (I41/a).  
However, we checked the reflections carefully and confirmed the breaking 
of the extinction rule of I41/a clearly.
;
_vrf_PLAT112_BI2C_LT             
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem         I        100 %Fit  
RESPONSE: 
The crystal has pseudo symmetry of higher symmetric space group (I41/a).  
However, we checked the reflections carefully and confirmed the breaking 
of the extinction rule of I41/a clearly.
;
_vrf_PLAT113_BI2C_LT             
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group      I41/a Check 
RESPONSE: 
The crystal has pseudo symmetry of higher symmetric space group (I41/a).  
However, we checked the reflections carefully and confirmed the breaking 
of the extinction rule of I41/a clearly.
;
_vrf_PLAT915_BI2C_LT             
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         37 %     
RESPONSE: 
The system consists only of light elements, C, H, and N.  Therefore, 
the calculation of the Flack coefficient is not considered.
;
# end Validation Reply Form



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        bis-(1H-benzimidazol-2-yl)-methane
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
_exptl_crystal_preparation       'dielectric properties'
####################################################################### 
# 
# 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_BI2C-MeOH
_database_code_depnum_ccdc_archive 'CCDC 1989818'
loop_
_audit_author_name
_audit_author_address
'Sachio Horiuchi'
;National Institute of Advanced Science and Technology 
Japan
;
_audit_update_record             
;
2020-03-11 deposited with the CCDC.	2020-05-13 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C31 H28 N8 O'
_chemical_formula_moiety         'C31 H28 N8 O'
_chemical_formula_weight         528.62
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
#------------------------------------------------------------------------------
_cell_length_a                   22.088(3)
_cell_length_b                   5.5860(7)
_cell_length_c                   24.017(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 115.257(3)
_cell_angle_gamma                90.0000
_cell_volume                     2680.0(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4556
_cell_measurement_theta_min      3.31
_cell_measurement_theta_max      27.49
_cell_measurement_temperature    295
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.070
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1112.00
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.873
_exptl_absorpt_correction_T_max  0.994

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

_diffrn_ambient_temperature      295
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.629
_diffrn_reflns_number            12993
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         3.308
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       30
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3047
_reflns_number_gt                2379
_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          0.0562
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1018
_refine_ls_wR_factor_gt          0.0923
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3047
_refine_ls_number_parameters     199
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0413P)²+1.0644P] 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         0.15
_refine_diff_density_min         -0.13
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0035(5)

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)
;
O O 0.0106 0.0060
;
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
O1 O 0.000000 0.4618(3) 0.250000 0.0863(6) Uani 1 2 d S T P . .
N1 N 0.05156(6) 0.20362(18) 0.02462(5) 0.0438(3) Uani 1 1 d . . . . .
H11 H 0.031785 0.069056 0.011202 0.053 Uiso 0.5 1 calc R U P . .
N2 N 0.08875(5) 0.53044(18) 0.08273(5) 0.0433(3) Uani 1 1 d . . . . .
H12 H 0.096062 0.632953 0.111613 0.052 Uiso 0.5 1 calc R U P . .
N3 N 0.10783(5) -0.08568(19) 0.16894(5) 0.0429(3) Uani 1 1 d . . . . .
H13A H 0.102983 -0.167120 0.136915 0.051 Uiso 0.5 1 calc R U P . .
N4 N 0.09345(6) 0.19777(19) 0.22721(5) 0.0451(3) Uani 1 1 d . . . . .
H14 H 0.078107 0.322982 0.237656 0.054 Uiso 0.5 1 calc R U P . .
C1 C 0.08721(7) 0.3384(2) 0.00004(6) 0.0415(3) Uani 1 1 d . . . . .
C2 C 0.10263(8) 0.3012(3) -0.04969(7) 0.0563(4) Uani 1 1 d . . . . .
H1 H 0.088068 0.164648 -0.073954 0.068 Uiso 1 1 calc R U . . .
C3 C 0.14001(8) 0.4722(3) -0.06191(8) 0.0601(4) Uani 1 1 d . . . . .
H2 H 0.150809 0.450303 -0.094995 0.072 Uiso 1 1 calc R U . . .
C4 C 0.16206(7) 0.6768(3) -0.02608(7) 0.0562(4) Uani 1 1 d . . . . .
H3 H 0.186977 0.789661 -0.035828 0.067 Uiso 1 1 calc R U . . .
C5 C 0.14772(7) 0.7159(2) 0.02359(7) 0.0510(4) Uani 1 1 d . . . . .
H4 H 0.162621 0.852777 0.047665 0.061 Uiso 1 1 calc R U . . .
C6 C 0.11021(6) 0.5436(2) 0.03648(6) 0.0398(3) Uani 1 1 d . . . . .
C7 C 0.05439(6) 0.3264(2) 0.07342(6) 0.0395(3) Uani 1 1 d . . . . .
C8 C 0.02455(7) 0.2363(3) 0.11468(6) 0.0485(3) Uani 1 1 d . . . . .
H5 H -0.011367 0.125490 0.091949 0.058 Uiso 1 1 calc R U . . .
H6 H 0.005429 0.369724 0.127560 0.058 Uiso 1 1 calc R U . . .
C9 C 0.07504(6) 0.1130(2) 0.17040(6) 0.0404(3) Uani 1 1 d . . . . .
C10 C 0.15137(6) -0.1342(2) 0.22966(6) 0.0398(3) Uani 1 1 d . . . . .
C11 C 0.19733(7) -0.3176(3) 0.25529(7) 0.0520(4) Uani 1 1 d . . . . .
H7 H 0.203374 -0.436376 0.230987 0.062 Uiso 1 1 calc R U . . .
C12 C 0.23354(8) -0.3161(3) 0.31816(7) 0.0602(4) Uani 1 1 d . . . . .
H8 H 0.264792 -0.436469 0.336691 0.072 Uiso 1 1 calc R U . . .
C13 C 0.22475(8) -0.1399(3) 0.35473(7) 0.0627(4) Uani 1 1 d . . . . .
H9 H 0.250047 -0.145513 0.397142 0.075 Uiso 1 1 calc R U . . .
C14 C 0.17935(8) 0.0434(3) 0.32962(7) 0.0581(4) Uani 1 1 d . . . . .
H10 H 0.173719 0.162032 0.354165 0.070 Uiso 1 1 calc R U . . .
C15 C 0.14231(7) 0.0433(2) 0.26602(6) 0.0421(3) Uani 1 1 d . . . . .
C16 C 0.000000 0.7036(6) 0.250000 0.1090(18) Uani 1 2 d S T P . .
H15A H 0.032(4) 0.776(10) 0.244(5) 0.119(19) Uiso 0.5 1 d . . P . .
H16B H -0.001(4) 0.756(9) 0.292(2) 0.103(17) Uiso 0.5 1 d . . P . .
H17C H -0.048(3) 0.737(9) 0.214(3) 0.12(2) Uiso 0.5 1 d . . P . .
H18 H 0.031(2) 0.377(9) 0.243(2) 0.130(18) Uiso 0.5 1 d . . P . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_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
O1 C16 1.351(4) . ?
O1 H18 0.91(5) . ?
N1 C7 1.3362(16) . ?
N1 C1 1.3902(16) . ?
N1 H11 0.8600 . ?
N2 C7 1.3343(16) . ?
N2 C6 1.3833(16) . ?
N2 H12 0.8600 . ?
N3 C9 1.3339(16) . ?
N3 C10 1.3887(16) . ?
N3 H13A 0.8600 . ?
N4 C9 1.3333(16) . ?
N4 C15 1.3854(17) . ?
N4 H14 0.8600 . ?
C1 C2 1.3902(19) . ?
C1 C6 1.3993(17) . ?
C2 C3 1.374(2) . ?
C2 H1 0.9300 . ?
C3 C4 1.388(2) . ?
C3 H2 0.9300 . ?
C4 C5 1.376(2) . ?
C4 H3 0.9300 . ?
C5 C6 1.3882(18) . ?
C5 H4 0.9300 . ?
C7 C8 1.4923(18) . ?
C8 C9 1.4952(18) . ?
C8 H5 0.9700 . ?
C8 H6 0.9700 . ?
C10 C11 1.3877(19) . ?
C10 C15 1.3911(17) . ?
C11 C12 1.375(2) . ?
C11 H7 0.9300 . ?
C12 C13 1.387(2) . ?
C12 H8 0.9300 . ?
C13 C14 1.379(2) . ?
C13 H9 0.9300 . ?
C14 C15 1.3915(19) . ?
C14 H10 0.9300 . ?
C16 H15A 0.87(6) . ?
C16 H16B 1.05(5) . ?
C16 H17C 1.06(5) . ?
C16 H15A 0.87(6) 2 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 O1 H18 121(3) . . ?
C7 N1 C1 105.76(10) . . ?
C7 N1 H11 127.1 . . ?
C1 N1 H11 127.1 . . ?
C7 N2 C6 106.03(10) . . ?
C7 N2 H12 127.0 . . ?
C6 N2 H12 127.0 . . ?
C9 N3 C10 105.98(10) . . ?
C9 N3 H13A 127.0 . . ?
C10 N3 H13A 127.0 . . ?
C9 N4 C15 106.09(10) . . ?
C9 N4 H14 127.0 . . ?
C15 N4 H14 127.0 . . ?
N1 C1 C2 132.42(12) . . ?
N1 C1 C6 107.36(11) . . ?
C2 C1 C6 120.21(12) . . ?
C3 C2 C1 118.00(14) . . ?
C3 C2 H1 121.0 . . ?
C1 C2 H1 121.0 . . ?
C2 C3 C4 121.60(14) . . ?
C2 C3 H2 119.2 . . ?
C4 C3 H2 119.2 . . ?
C5 C4 C3 121.22(14) . . ?
C5 C4 H3 119.4 . . ?
C3 C4 H3 119.4 . . ?
C4 C5 C6 117.61(13) . . ?
C4 C5 H4 121.2 . . ?
C6 C5 H4 121.2 . . ?
N2 C6 C5 131.11(12) . . ?
N2 C6 C1 107.54(11) . . ?
C5 C6 C1 121.35(12) . . ?
N2 C7 N1 113.31(11) . . ?
N2 C7 C8 123.89(11) . . ?
N1 C7 C8 122.73(12) . . ?
C7 C8 C9 112.18(11) . . ?
C7 C8 H5 109.2 . . ?
C9 C8 H5 109.2 . . ?
C7 C8 H6 109.2 . . ?
C9 C8 H6 109.2 . . ?
H5 C8 H6 107.9 . . ?
N4 C9 N3 112.98(11) . . ?
N4 C9 C8 122.53(12) . . ?
N3 C9 C8 124.45(11) . . ?
C11 C10 N3 131.13(12) . . ?
C11 C10 C15 121.45(12) . . ?
N3 C10 C15 107.42(11) . . ?
C12 C11 C10 117.07(14) . . ?
C12 C11 H7 121.5 . . ?
C10 C11 H7 121.5 . . ?
C11 C12 C13 121.83(15) . . ?
C11 C12 H8 119.1 . . ?
C13 C12 H8 119.1 . . ?
C14 C13 C12 121.47(14) . . ?
C14 C13 H9 119.3 . . ?
C12 C13 H9 119.3 . . ?
C13 C14 C15 117.20(14) . . ?
C13 C14 H10 121.4 . . ?
C15 C14 H10 121.4 . . ?
N4 C15 C10 107.52(11) . . ?
N4 C15 C14 131.51(13) . . ?
C10 C15 C14 120.97(13) . . ?
O1 C16 H15A 118(3) . . ?
O1 C16 H16B 106(3) . . ?
H15A C16 H16B 112(5) . . ?
O1 C16 H17C 100(3) . . ?
H15A C16 H17C 113(5) . . ?
H16B C16 H17C 107(4) . . ?
O1 C16 H15A 118(3) . 2 ?
H15A C16 H15A 125(7) . 2 ?
H16B C16 H15A 51(5) . 2 ?
H17C C16 H15A 56(5) . 2 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 C1 C2 178.61(15) . . . . ?
C7 N1 C1 C6 -0.31(14) . . . . ?
N1 C1 C2 C3 -179.57(14) . . . . ?
C6 C1 C2 C3 -0.8(2) . . . . ?
C1 C2 C3 C4 0.0(2) . . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
C7 N2 C6 C5 179.98(13) . . . . ?
C7 N2 C6 C1 -0.26(13) . . . . ?
C4 C5 C6 N2 179.17(13) . . . . ?
C4 C5 C6 C1 -0.6(2) . . . . ?
N1 C1 C6 N2 0.36(14) . . . . ?
C2 C1 C6 N2 -178.72(12) . . . . ?
N1 C1 C6 C5 -179.85(11) . . . . ?
C2 C1 C6 C5 1.06(19) . . . . ?
C6 N2 C7 N1 0.07(14) . . . . ?
C6 N2 C7 C8 177.35(11) . . . . ?
C1 N1 C7 N2 0.16(14) . . . . ?
C1 N1 C7 C8 -177.16(11) . . . . ?
N2 C7 C8 C9 -80.96(16) . . . . ?
N1 C7 C8 C9 96.07(15) . . . . ?
C15 N4 C9 N3 0.27(15) . . . . ?
C15 N4 C9 C8 -177.66(11) . . . . ?
C10 N3 C9 N4 -0.25(14) . . . . ?
C10 N3 C9 C8 177.63(12) . . . . ?
C7 C8 C9 N4 114.88(14) . . . . ?
C7 C8 C9 N3 -62.81(17) . . . . ?
C9 N3 C10 C11 -179.99(14) . . . . ?
C9 N3 C10 C15 0.12(13) . . . . ?
N3 C10 C11 C12 -179.91(13) . . . . ?
C15 C10 C11 C12 0.0(2) . . . . ?
C10 C11 C12 C13 0.1(2) . . . . ?
C11 C12 C13 C14 -0.3(2) . . . . ?
C12 C13 C14 C15 0.5(2) . . . . ?
C9 N4 C15 C10 -0.18(14) . . . . ?
C9 N4 C15 C14 179.77(14) . . . . ?
C11 C10 C15 N4 -179.87(12) . . . . ?
N3 C10 C15 N4 0.03(14) . . . . ?
C11 C10 C15 C14 0.2(2) . . . . ?
N3 C10 C15 C14 -179.92(12) . . . . ?
C13 C14 C15 N4 179.68(14) . . . . ?
C13 C14 C15 C10 -0.4(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H18 N4 . . . 2.7748(17) 0.91(6) 1.86(6) 178(4) no
O1 H18 N4 . 2_555 2_555 2.7748(17) 0.91(6) 1.86(6) 178(4) no
N1 H11 N1 . . 5_555 3.0762(15) 0.860 2.258 159.0 no
N2 H12 N3 . . 1_565 2.8841(16) 0.860 2.032 170.9 no
N3 H13A N2 . . 1_545 2.8841(16) 0.860 2.073 157.0 no
N4 H14 O1 . . . 2.7748(17) 0.860 2.025 145.1 no

#==============================================================================
# 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
#==============================================================================
_chemical_name_systematic        
'bis-(1H-benzimidazol-2-yl)-methane methanol solvate'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_BI2C-b
_database_code_depnum_ccdc_archive 'CCDC 1989816'
loop_
_audit_author_name
_audit_author_address
'Sachio Horiuchi'
;National Institute of Advanced Science and Technology 
Japan
;
_audit_update_record             
;
2020-03-11 deposited with the CCDC.	2020-05-13 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C15 H12 N4'
_chemical_formula_moiety         'C15 H12 N4'
_chemical_formula_weight         248.29
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   18.3296(17)
_cell_length_b                   15.7595(15)
_cell_length_c                   18.3254(16)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.612(3)
_cell_angle_gamma                90.0000
_cell_volume                     5293.3(8)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    13315
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      27.49
_cell_measurement_temperature    295
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.230
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2080.00
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.820
_exptl_absorpt_correction_T_max  0.982

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

_diffrn_ambient_temperature      295
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.629
_diffrn_reflns_number            52125
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         3.021
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             12005
_reflns_number_gt                6915
_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          0.1199
_refine_ls_R_factor_gt           0.0689
_refine_ls_wR_factor_ref         0.1955
_refine_ls_wR_factor_gt          0.1621
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         12005
_refine_ls_number_parameters     718
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0725P)²+1.0956P] 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         0.17
_refine_diff_density_min         -0.16
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0042(8)

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 0.33129(10) 0.36510(11) 0.31985(8) 0.0549(5) Uani 1 1 d . . . . .
N2 N 0.32003(11) 0.34535(12) 0.43892(8) 0.0664(5) Uani 1 1 d . . . . .
N3 N 0.15638(11) 0.18610(11) 0.31430(8) 0.0567(5) Uani 1 1 d . . . . .
N4 N 0.16256(10) 0.24653(11) 0.42384(8) 0.0570(5) Uani 1 1 d . . . . .
N5 N 0.34114(10) 0.25166(11) 0.56720(8) 0.0542(4) Uani 1 1 d . . . . .
N6 N 0.33818(10) 0.18419(11) 0.67357(8) 0.0557(5) Uani 1 1 d . . . . .
N7 N 0.17740(12) 0.35225(13) 0.54941(9) 0.0690(6) Uani 1 1 d . . . . .
N8 N 0.16898(10) 0.36252(11) 0.66956(8) 0.0584(5) Uani 1 1 d . . . . .
N9 N 0.07522(10) -0.11789(11) 0.41875(9) 0.0536(4) Uani 1 1 d . . . . .
N10 N 0.19450(10) -0.09569(13) 0.42469(11) 0.0709(5) Uani 1 1 d . . . . .
N11 N 0.17542(10) -0.00290(12) 0.58650(10) 0.0560(5) Uani 1 1 d . . . . .
N12 N 0.07083(10) 0.06839(11) 0.58563(9) 0.0572(5) Uani 1 1 d . . . . .
N13 N 0.32430(10) -0.00299(12) 0.40925(10) 0.0558(5) Uani 1 1 d . . . . .
N14 N 0.42962(10) 0.06732(11) 0.41020(9) 0.0572(5) Uani 1 1 d . . . . .
N15 N 0.42409(11) -0.11624(12) 0.58159(9) 0.0570(5) Uani 1 1 d . . . . .
N16 N 0.30516(10) -0.09733(13) 0.56925(11) 0.0707(5) Uani 1 1 d . . . . .
C1 C 0.28022(13) 0.22634(14) 0.35888(11) 0.0594(6) Uani 1 1 d . . . . .
H1 H 0.302683 0.186092 0.392274 0.071 Uiso 1 1 calc R U . . .
H2 H 0.293169 0.209722 0.309725 0.071 Uiso 1 1 calc R U . . .
C2 C 0.31084(11) 0.31216(13) 0.37387(9) 0.0502(5) Uani 1 1 d . . . . .
C3 C 0.35597(12) 0.43866(14) 0.35221(10) 0.0561(5) Uani 1 1 d . . . . .
C4 C 0.38265(16) 0.51348(17) 0.32366(13) 0.0792(8) Uani 1 1 d . . . . .
H4 H 0.387270 0.521204 0.273609 0.095 Uiso 1 1 calc R U . . .
C5 C 0.40209(18) 0.57602(19) 0.37242(15) 0.0983(10) Uani 1 1 d . . . . .
H5 H 0.421078 0.626834 0.355139 0.118 Uiso 1 1 calc R U . . .
C6 C 0.3939(2) 0.5647(2) 0.44649(16) 0.1166(13) Uani 1 1 d . . . . .
H6 H 0.406829 0.608625 0.477980 0.140 Uiso 1 1 calc R U . . .
C7 C 0.3674(2) 0.4908(2) 0.47505(14) 0.1052(11) Uani 1 1 d . . . . .
H7 H 0.362231 0.483850 0.525127 0.126 Uiso 1 1 calc R U . . .
C8 C 0.34826(14) 0.42625(16) 0.42643(11) 0.0654(6) Uani 1 1 d . . . . .
C9 C 0.19948(12) 0.22089(12) 0.36618(9) 0.0501(5) Uani 1 1 d . . . . .
C10 C 0.08534(13) 0.18902(13) 0.33907(10) 0.0553(5) Uani 1 1 d . . . . .
C11 C 0.02055(15) 0.16080(16) 0.30914(13) 0.0745(7) Uani 1 1 d . . . . .
H9 H 0.018519 0.135522 0.263309 0.089 Uiso 1 1 calc R U . . .
C12 C -0.04124(16) 0.17182(17) 0.35044(15) 0.0808(7) Uani 1 1 d . . . . .
H10 H -0.086041 0.153830 0.331835 0.097 Uiso 1 1 calc R U . . .
C13 C -0.03824(15) 0.20905(17) 0.41898(14) 0.0782(7) Uani 1 1 d . . . . .
H11 H -0.080930 0.215104 0.445457 0.094 Uiso 1 1 calc R U . . .
C14 C 0.02675(15) 0.23724(15) 0.44858(12) 0.0695(6) Uani 1 1 d . . . . .
H12 H 0.028490 0.262228 0.494542 0.083 Uiso 1 1 calc R U . . .
C15 C 0.08991(13) 0.22721(13) 0.40761(10) 0.0543(5) Uani 1 1 d . . . . .
C16 C 0.21805(12) 0.22665(13) 0.62173(11) 0.0561(5) Uani 1 1 d . . . . .
H13 H 0.199325 0.192426 0.581718 0.067 Uiso 1 1 calc R U . . .
H14 H 0.200360 0.202064 0.666725 0.067 Uiso 1 1 calc R U . . .
C17 C 0.29927(12) 0.22166(12) 0.62202(9) 0.0497(5) Uani 1 1 d . . . . .
C18 C 0.41280(12) 0.23186(13) 0.58428(10) 0.0530(5) Uani 1 1 d . . . . .
C19 C 0.47733(14) 0.24400(16) 0.54749(12) 0.0684(6) Uani 1 1 d . . . . .
H16 H 0.478436 0.272122 0.502895 0.082 Uiso 1 1 calc R U . . .
C20 C 0.54007(15) 0.21258(17) 0.57977(14) 0.0766(7) Uani 1 1 d . . . . .
H17 H 0.584411 0.219315 0.556274 0.092 Uiso 1 1 calc R U . . .
C21 C 0.53844(16) 0.17103(17) 0.64676(15) 0.0805(7) Uani 1 1 d . . . . .
H18 H 0.581772 0.151149 0.667340 0.097 Uiso 1 1 calc R U . . .
C22 C 0.47403(15) 0.15877(16) 0.68312(13) 0.0733(7) Uani 1 1 d . . . . .
H19 H 0.473149 0.130532 0.727667 0.088 Uiso 1 1 calc R U . . .
C23 C 0.41009(13) 0.19000(13) 0.65114(10) 0.0546(5) Uani 1 1 d . . . . .
C24 C 0.18799(11) 0.31395(13) 0.61445(9) 0.0511(5) Uani 1 1 d . . . . .
C25 C 0.14929(14) 0.43193(16) 0.56286(11) 0.0681(7) Uani 1 1 d . . . . .
C26 C 0.1286(2) 0.4978(2) 0.51749(14) 0.1109(12) Uani 1 1 d . . . . .
H21 H 0.132342 0.493552 0.467044 0.133 Uiso 1 1 calc R U . . .
C27 C 0.1023(2) 0.5697(2) 0.55017(16) 0.1169(13) Uani 1 1 d . . . . .
H22 H 0.088481 0.615420 0.521085 0.140 Uiso 1 1 calc R U . . .
C28 C 0.09577(19) 0.57621(19) 0.62500(15) 0.0982(10) Uani 1 1 d . . . . .
H23 H 0.076835 0.625617 0.645092 0.118 Uiso 1 1 calc R U . . .
C29 C 0.11663(16) 0.51137(17) 0.66988(13) 0.0784(8) Uani 1 1 d . . . . .
H24 H 0.112770 0.516178 0.720274 0.094 Uiso 1 1 calc R U . . .
C30 C 0.14401(12) 0.43742(14) 0.63803(10) 0.0575(5) Uani 1 1 d . . . . .
C31 C 0.11574(13) 0.02310(13) 0.46466(11) 0.0594(6) Uani 1 1 d . . . . .
H25 H 0.067864 0.041576 0.448133 0.071 Uiso 1 1 calc R U . . .
H26 H 0.151382 0.061890 0.444584 0.071 Uiso 1 1 calc R U . . .
C32 C 0.12978(11) -0.06367(13) 0.43534(10) 0.0514(5) Uani 1 1 d . . . . .
C33 C 0.10709(11) -0.19185(14) 0.39503(10) 0.0542(5) Uani 1 1 d . . . . .
C34 C 0.07810(14) -0.26891(16) 0.37134(13) 0.0718(7) Uani 1 1 d . . . . .
H28 H 0.027992 -0.277993 0.369053 0.086 Uiso 1 1 calc R U . . .
C35 C 0.12640(17) -0.33055(18) 0.35162(16) 0.0908(9) Uani 1 1 d . . . . .
H29 H 0.108747 -0.382321 0.334654 0.109 Uiso 1 1 calc R U . . .
C36 C 0.20057(18) -0.3179(2) 0.3563(2) 0.1147(12) Uani 1 1 d . . . . .
H30 H 0.231863 -0.361583 0.343068 0.138 Uiso 1 1 calc R U . . .
C37 C 0.22932(16) -0.2426(2) 0.37977(19) 0.1098(12) Uani 1 1 d . . . . .
H31 H 0.279538 -0.234594 0.382474 0.132 Uiso 1 1 calc R U . . .
C38 C 0.18157(12) -0.17847(16) 0.39954(13) 0.0665(6) Uani 1 1 d . . . . .
C39 C 0.11908(11) 0.02856(13) 0.54596(11) 0.0505(5) Uani 1 1 d . . . . .
C40 C 0.16221(11) 0.01828(13) 0.65847(11) 0.0531(5) Uani 1 1 d . . . . .
C41 C 0.20152(14) 0.00472(15) 0.72243(13) 0.0691(6) Uani 1 1 d . . . . .
H33 H 0.245209 -0.025299 0.722778 0.083 Uiso 1 1 calc R U . . .
C42 C 0.17284(17) 0.03778(17) 0.78535(14) 0.0789(8) Uani 1 1 d . . . . .
H34 H 0.197961 0.030183 0.829221 0.095 Uiso 1 1 calc R U . . .
C43 C 0.10721(17) 0.08234(18) 0.78522(14) 0.0825(8) Uani 1 1 d . . . . .
H35 H 0.089468 0.103607 0.828916 0.099 Uiso 1 1 calc R U . . .
C44 C 0.06809(14) 0.09552(16) 0.72164(13) 0.0729(7) Uani 1 1 d . . . . .
H36 H 0.024266 0.125259 0.721614 0.087 Uiso 1 1 calc R U . . .
C45 C 0.09660(12) 0.06264(13) 0.65732(11) 0.0556(5) Uani 1 1 d . . . . .
C46 C 0.38391(13) 0.02279(14) 0.53123(11) 0.0599(6) Uani 1 1 d . . . . .
H37 H 0.348251 0.061645 0.551173 0.072 Uiso 1 1 calc R U . . .
H38 H 0.431735 0.041392 0.547807 0.072 Uiso 1 1 calc R U . . .
C47 C 0.38082(11) 0.02861(13) 0.45002(11) 0.0515(5) Uani 1 1 d . . . . .
C48 C 0.33827(12) 0.01826(13) 0.33715(11) 0.0555(5) Uani 1 1 d . . . . .
C49 C 0.29853(14) 0.00582(16) 0.27315(13) 0.0710(7) Uani 1 1 d . . . . .
H40 H 0.254362 -0.023235 0.272664 0.085 Uiso 1 1 calc R U . . .
C50 C 0.32798(17) 0.03881(18) 0.21036(14) 0.0803(8) Uani 1 1 d . . . . .
H41 H 0.302812 0.032173 0.166394 0.096 Uiso 1 1 calc R U . . .
C51 C 0.39397(18) 0.08154(18) 0.21084(14) 0.0842(8) Uani 1 1 d . . . . .
H42 H 0.412326 0.102363 0.167247 0.101 Uiso 1 1 calc R U . . .
C52 C 0.43282(15) 0.09377(17) 0.27441(13) 0.0759(7) Uani 1 1 d . . . . .
H43 H 0.477071 0.122652 0.274487 0.091 Uiso 1 1 calc R U . . .
C53 C 0.40414(12) 0.06177(14) 0.33855(12) 0.0572(5) Uani 1 1 d . . . . .
C54 C 0.36992(11) -0.06384(13) 0.56129(10) 0.0516(5) Uani 1 1 d . . . . .
C55 C 0.39235(12) -0.19074(14) 0.60482(11) 0.0564(5) Uani 1 1 d . . . . .
C56 C 0.42181(14) -0.26622(17) 0.63116(14) 0.0773(7) Uani 1 1 d . . . . .
H45 H 0.471928 -0.273721 0.636291 0.093 Uiso 1 1 calc R U . . .
C57 C 0.37370(18) -0.3288(2) 0.64916(17) 0.0985(10) Uani 1 1 d . . . . .
H46 H 0.391410 -0.379814 0.667787 0.118 Uiso 1 1 calc R U . . .
C58 C 0.29895(19) -0.3181(2) 0.6403(2) 0.1183(12) Uani 1 1 d . . . . .
H47 H 0.267782 -0.362451 0.652081 0.142 Uiso 1 1 calc R U . . .
C59 C 0.27001(16) -0.2434(2) 0.61438(19) 0.1079(11) Uani 1 1 d . . . . .
H48 H 0.219859 -0.236388 0.609012 0.130 Uiso 1 1 calc R U . . .
C60 C 0.31807(13) -0.17865(16) 0.59649(13) 0.0676(6) Uani 1 1 d . . . . .
H3 H 0.3310(14) 0.3487(17) 0.2675(14) 0.096(8) Uiso 1 1 d . . . . .
H8 H 0.1689(14) 0.1643(16) 0.2635(13) 0.087(8) Uiso 1 1 d . . . . .
H15 H 0.3243(13) 0.2821(16) 0.5272(12) 0.078(7) Uiso 1 1 d . . . . .
H20 H 0.1783(16) 0.3164(18) 0.5043(14) 0.106(9) Uiso 1 1 d . . . . .
H27 H 0.0252(15) -0.1032(16) 0.4195(12) 0.083(8) Uiso 1 1 d . . . . .
H32 H 0.2172(15) -0.0319(17) 0.5687(12) 0.083(8) Uiso 1 1 d . . . . .
H39 H 0.2825(15) -0.0345(16) 0.4260(12) 0.081(8) Uiso 1 1 d . . . . .
H44 H 0.4730(15) -0.1041(16) 0.5813(12) 0.079(8) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_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 C2 1.351(2) . ?
N1 C3 1.376(3) . ?
N1 H3 0.99(2) . ?
N2 C2 1.311(2) . ?
N2 C8 1.396(3) . ?
N3 C9 1.346(2) . ?
N3 C10 1.384(3) . ?
N3 H8 1.02(2) . ?
N4 C9 1.324(2) . ?
N4 C15 1.395(3) . ?
N5 C17 1.356(2) . ?
N5 C18 1.383(3) . ?
N5 H15 0.93(2) . ?
N6 C17 1.317(2) . ?
N6 C23 1.388(3) . ?
N7 C24 1.348(2) . ?
N7 C25 1.381(3) . ?
N7 H20 1.00(3) . ?
N8 C24 1.317(2) . ?
N8 C30 1.390(3) . ?
N9 C32 1.348(3) . ?
N9 C33 1.376(3) . ?
N9 H27 0.95(3) . ?
N10 C32 1.306(3) . ?
N10 C38 1.403(3) . ?
N11 C39 1.359(3) . ?
N11 C40 1.384(3) . ?
N11 H32 0.95(3) . ?
N12 C39 1.311(3) . ?
N12 C45 1.394(3) . ?
N13 C47 1.365(3) . ?
N13 C48 1.389(3) . ?
N13 H39 0.97(3) . ?
N14 C47 1.311(3) . ?
N14 C53 1.392(3) . ?
N15 C54 1.341(3) . ?
N15 C55 1.380(3) . ?
N15 H44 0.92(3) . ?
N16 C54 1.309(3) . ?
N16 C60 1.395(3) . ?
C1 C2 1.489(3) . ?
C1 C9 1.490(3) . ?
C1 H1 0.9700 . ?
C1 H2 0.9700 . ?
C3 C4 1.382(3) . ?
C3 C8 1.383(3) . ?
C4 C5 1.375(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.369(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.394(3) . ?
C7 H7 0.9300 . ?
C10 C11 1.377(3) . ?
C10 C15 1.395(3) . ?
C11 C12 1.380(4) . ?
C11 H9 0.9300 . ?
C12 C13 1.387(4) . ?
C12 H10 0.9300 . ?
C13 C14 1.377(4) . ?
C13 H11 0.9300 . ?
C14 C15 1.395(3) . ?
C14 H12 0.9300 . ?
C16 C24 1.488(3) . ?
C16 C17 1.491(3) . ?
C16 H13 0.9700 . ?
C16 H14 0.9700 . ?
C18 C19 1.381(3) . ?
C18 C23 1.393(3) . ?
C19 C20 1.380(3) . ?
C19 H16 0.9300 . ?
C20 C21 1.392(4) . ?
C20 H17 0.9300 . ?
C21 C22 1.376(4) . ?
C21 H18 0.9300 . ?
C22 C23 1.394(3) . ?
C22 H19 0.9300 . ?
C25 C26 1.380(3) . ?
C25 C30 1.384(3) . ?
C26 C27 1.372(4) . ?
C26 H21 0.9300 . ?
C27 C28 1.382(4) . ?
C27 H22 0.9300 . ?
C28 C29 1.364(3) . ?
C28 H23 0.9300 . ?
C29 C30 1.399(3) . ?
C29 H24 0.9300 . ?
C31 C32 1.493(3) . ?
C31 C39 1.493(3) . ?
C31 H25 0.9700 . ?
C31 H26 0.9700 . ?
C33 C38 1.383(3) . ?
C33 C34 1.393(3) . ?
C34 C35 1.366(3) . ?
C34 H28 0.9300 . ?
C35 C36 1.376(4) . ?
C35 H29 0.9300 . ?
C36 C37 1.366(4) . ?
C36 H30 0.9300 . ?
C37 C38 1.388(3) . ?
C37 H31 0.9300 . ?
C40 C41 1.386(3) . ?
C40 C45 1.391(3) . ?
C41 C42 1.375(4) . ?
C41 H33 0.9300 . ?
C42 C43 1.393(4) . ?
C42 H34 0.9300 . ?
C43 C44 1.377(3) . ?
C43 H35 0.9300 . ?
C44 C45 1.394(3) . ?
C44 H36 0.9300 . ?
C46 C47 1.491(3) . ?
C46 C54 1.495(3) . ?
C46 H37 0.9700 . ?
C46 H38 0.9700 . ?
C48 C49 1.388(3) . ?
C48 C53 1.389(3) . ?
C49 C50 1.378(4) . ?
C49 H40 0.9300 . ?
C50 C51 1.384(4) . ?
C50 H41 0.9300 . ?
C51 C52 1.372(4) . ?
C51 H42 0.9300 . ?
C52 C53 1.388(3) . ?
C52 H43 0.9300 . ?
C55 C60 1.382(3) . ?
C55 C56 1.391(3) . ?
C56 C57 1.366(4) . ?
C56 H45 0.9300 . ?
C57 C58 1.388(4) . ?
C57 H46 0.9300 . ?
C58 C59 1.373(4) . ?
C58 H47 0.9300 . ?
C59 C60 1.390(4) . ?
C59 H48 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
C2 N1 C3 107.28(16) . . ?
C2 N1 H3 123.3(15) . . ?
C3 N1 H3 129.3(15) . . ?
C2 N2 C8 105.04(16) . . ?
C9 N3 C10 107.56(16) . . ?
C9 N3 H8 130.2(14) . . ?
C10 N3 H8 122.1(14) . . ?
C9 N4 C15 104.97(16) . . ?
C17 N5 C18 107.30(16) . . ?
C17 N5 H15 125.5(15) . . ?
C18 N5 H15 127.2(15) . . ?
C17 N6 C23 105.46(16) . . ?
C24 N7 C25 107.45(17) . . ?
C24 N7 H20 118.2(16) . . ?
C25 N7 H20 132.1(16) . . ?
C24 N8 C30 105.27(16) . . ?
C32 N9 C33 106.96(18) . . ?
C32 N9 H27 123.9(16) . . ?
C33 N9 H27 128.9(16) . . ?
C32 N10 C38 104.94(18) . . ?
C39 N11 C40 107.05(18) . . ?
C39 N11 H32 126.7(14) . . ?
C40 N11 H32 126.2(14) . . ?
C39 N12 C45 105.53(17) . . ?
C47 N13 C48 106.62(19) . . ?
C47 N13 H39 127.8(14) . . ?
C48 N13 H39 125.5(13) . . ?
C47 N14 C53 105.77(17) . . ?
C54 N15 C55 107.23(19) . . ?
C54 N15 H44 126.2(16) . . ?
C55 N15 H44 126.5(16) . . ?
C54 N16 C60 105.07(18) . . ?
C2 C1 C9 114.12(18) . . ?
C2 C1 H1 108.7 . . ?
C9 C1 H1 108.7 . . ?
C2 C1 H2 108.7 . . ?
C9 C1 H2 108.7 . . ?
H1 C1 H2 107.6 . . ?
N2 C2 N1 112.71(19) . . ?
N2 C2 C1 125.07(18) . . ?
N1 C2 C1 122.21(16) . . ?
N1 C3 C4 132.21(19) . . ?
N1 C3 C8 105.55(18) . . ?
C4 C3 C8 122.2(2) . . ?
C5 C4 C3 117.1(2) . . ?
C5 C4 H4 121.4 . . ?
C3 C4 H4 121.4 . . ?
C4 C5 C6 121.1(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C7 C6 C5 122.0(3) . . ?
C7 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C6 C7 C8 117.7(2) . . ?
C6 C7 H7 121.2 . . ?
C8 C7 H7 121.2 . . ?
C3 C8 C7 119.8(2) . . ?
C3 C8 N2 109.42(18) . . ?
C7 C8 N2 130.7(2) . . ?
N4 C9 N3 112.8(2) . . ?
N4 C9 C1 124.81(17) . . ?
N3 C9 C1 122.41(17) . . ?
C11 C10 N3 132.0(2) . . ?
C11 C10 C15 122.8(2) . . ?
N3 C10 C15 105.20(18) . . ?
C10 C11 C12 116.8(2) . . ?
C10 C11 H9 121.6 . . ?
C12 C11 H9 121.6 . . ?
C11 C12 C13 121.7(3) . . ?
C11 C12 H10 119.2 . . ?
C13 C12 H10 119.2 . . ?
C14 C13 C12 121.3(2) . . ?
C14 C13 H11 119.4 . . ?
C12 C13 H11 119.4 . . ?
C13 C14 C15 118.1(2) . . ?
C13 C14 H12 121.0 . . ?
C15 C14 H12 121.0 . . ?
C10 C15 N4 109.52(18) . . ?
C10 C15 C14 119.4(2) . . ?
N4 C15 C14 131.01(19) . . ?
C24 C16 C17 114.71(18) . . ?
C24 C16 H13 108.6 . . ?
C17 C16 H13 108.6 . . ?
C24 C16 H14 108.6 . . ?
C17 C16 H14 108.6 . . ?
H13 C16 H14 107.6 . . ?
N6 C17 N5 112.4(2) . . ?
N6 C17 C16 124.00(18) . . ?
N5 C17 C16 123.51(17) . . ?
C19 C18 N5 132.4(2) . . ?
C19 C18 C23 122.3(2) . . ?
N5 C18 C23 105.26(18) . . ?
C20 C19 C18 117.1(2) . . ?
C20 C19 H16 121.5 . . ?
C18 C19 H16 121.5 . . ?
C19 C20 C21 121.4(2) . . ?
C19 C20 H17 119.3 . . ?
C21 C20 H17 119.3 . . ?
C22 C21 C20 121.3(2) . . ?
C22 C21 H18 119.3 . . ?
C20 C21 H18 119.3 . . ?
C21 C22 C23 118.0(2) . . ?
C21 C22 H19 121.0 . . ?
C23 C22 H19 121.0 . . ?
N6 C23 C18 109.56(18) . . ?
N6 C23 C22 130.5(2) . . ?
C18 C23 C22 119.9(2) . . ?
N8 C24 N7 112.39(19) . . ?
N8 C24 C16 124.72(17) . . ?
N7 C24 C16 122.89(18) . . ?
C26 C25 N7 132.6(2) . . ?
C26 C25 C30 122.1(2) . . ?
N7 C25 C30 105.34(18) . . ?
C27 C26 C25 117.0(2) . . ?
C27 C26 H21 121.5 . . ?
C25 C26 H21 121.5 . . ?
C26 C27 C28 122.0(3) . . ?
C26 C27 H22 119.0 . . ?
C28 C27 H22 119.0 . . ?
C29 C28 C27 121.1(3) . . ?
C29 C28 H23 119.5 . . ?
C27 C28 H23 119.5 . . ?
C28 C29 C30 118.2(2) . . ?
C28 C29 H24 120.9 . . ?
C30 C29 H24 120.9 . . ?
C25 C30 N8 109.54(18) . . ?
C25 C30 C29 119.8(2) . . ?
N8 C30 C29 130.70(19) . . ?
C32 C31 C39 113.99(17) . . ?
C32 C31 H25 108.8 . . ?
C39 C31 H25 108.8 . . ?
C32 C31 H26 108.8 . . ?
C39 C31 H26 108.8 . . ?
H25 C31 H26 107.6 . . ?
N10 C32 N9 113.23(19) . . ?
N10 C32 C31 124.6(2) . . ?
N9 C32 C31 122.13(19) . . ?
N9 C33 C38 105.91(19) . . ?
N9 C33 C34 132.4(2) . . ?
C38 C33 C34 121.6(2) . . ?
C35 C34 C33 117.1(2) . . ?
C35 C34 H28 121.4 . . ?
C33 C34 H28 121.4 . . ?
C34 C35 C36 121.6(3) . . ?
C34 C35 H29 119.2 . . ?
C36 C35 H29 119.2 . . ?
C37 C36 C35 121.6(3) . . ?
C37 C36 H30 119.2 . . ?
C35 C36 H30 119.2 . . ?
C36 C37 C38 118.2(3) . . ?
C36 C37 H31 120.9 . . ?
C38 C37 H31 120.9 . . ?
C33 C38 C37 119.9(2) . . ?
C33 C38 N10 108.94(19) . . ?
C37 C38 N10 131.2(2) . . ?
N12 C39 N11 112.62(18) . . ?
N12 C39 C31 124.08(18) . . ?
N11 C39 C31 123.17(19) . . ?
N11 C40 C41 132.4(2) . . ?
N11 C40 C45 105.46(17) . . ?
C41 C40 C45 122.1(2) . . ?
C42 C41 C40 116.8(2) . . ?
C42 C41 H33 121.6 . . ?
C40 C41 H33 121.6 . . ?
C41 C42 C43 121.8(2) . . ?
C41 C42 H34 119.1 . . ?
C43 C42 H34 119.1 . . ?
C44 C43 C42 121.3(2) . . ?
C44 C43 H35 119.4 . . ?
C42 C43 H35 119.4 . . ?
C43 C44 C45 117.6(3) . . ?
C43 C44 H36 121.2 . . ?
C45 C44 H36 121.2 . . ?
C40 C45 N12 109.34(18) . . ?
C40 C45 C44 120.4(2) . . ?
N12 C45 C44 130.3(2) . . ?
C47 C46 C54 114.77(17) . . ?
C47 C46 H37 108.6 . . ?
C54 C46 H37 108.6 . . ?
C47 C46 H38 108.6 . . ?
C54 C46 H38 108.6 . . ?
H37 C46 H38 107.6 . . ?
N14 C47 N13 112.55(18) . . ?
N14 C47 C46 124.41(18) . . ?
N13 C47 C46 122.98(19) . . ?
C49 C48 C53 122.3(2) . . ?
C49 C48 N13 132.0(2) . . ?
C53 C48 N13 105.70(18) . . ?
C50 C49 C48 116.5(3) . . ?
C50 C49 H40 121.8 . . ?
C48 C49 H40 121.8 . . ?
C49 C50 C51 121.9(2) . . ?
C49 C50 H41 119.1 . . ?
C51 C50 H41 119.1 . . ?
C52 C51 C50 121.3(2) . . ?
C52 C51 H42 119.4 . . ?
C50 C51 H42 119.4 . . ?
C51 C52 C53 118.0(3) . . ?
C51 C52 H43 121.0 . . ?
C53 C52 H43 121.0 . . ?
C52 C53 C48 120.1(2) . . ?
C52 C53 N14 130.5(2) . . ?
C48 C53 N14 109.36(18) . . ?
N16 C54 N15 113.0(2) . . ?
N16 C54 C46 124.7(2) . . ?
N15 C54 C46 122.34(19) . . ?
N15 C55 C60 105.48(19) . . ?
N15 C55 C56 132.2(2) . . ?
C60 C55 C56 122.3(2) . . ?
C57 C56 C55 116.9(2) . . ?
C57 C56 H45 121.6 . . ?
C55 C56 H45 121.6 . . ?
C56 C57 C58 121.5(3) . . ?
C56 C57 H46 119.3 . . ?
C58 C57 H46 119.3 . . ?
C59 C58 C57 121.5(3) . . ?
C59 C58 H47 119.3 . . ?
C57 C58 H47 119.3 . . ?
C58 C59 C60 117.9(3) . . ?
C58 C59 H48 121.1 . . ?
C60 C59 H48 121.1 . . ?
C55 C60 C59 119.9(2) . . ?
C55 C60 N16 109.2(2) . . ?
C59 C60 N16 130.8(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N2 C2 N1 0.3(3) . . . . ?
C8 N2 C2 C1 -178.7(2) . . . . ?
C3 N1 C2 N2 0.1(3) . . . . ?
C3 N1 C2 C1 179.2(2) . . . . ?
C9 C1 C2 N2 76.4(3) . . . . ?
C9 C1 C2 N1 -102.5(2) . . . . ?
C2 N1 C3 C4 -179.5(3) . . . . ?
C2 N1 C3 C8 -0.6(2) . . . . ?
N1 C3 C4 C5 179.2(3) . . . . ?
C8 C3 C4 C5 0.5(4) . . . . ?
C3 C4 C5 C6 -1.1(5) . . . . ?
C4 C5 C6 C7 1.1(6) . . . . ?
C5 C6 C7 C8 -0.2(6) . . . . ?
N1 C3 C8 C7 -178.7(3) . . . . ?
C4 C3 C8 C7 0.4(4) . . . . ?
N1 C3 C8 N2 0.8(3) . . . . ?
C4 C3 C8 N2 179.8(2) . . . . ?
C6 C7 C8 C3 -0.5(5) . . . . ?
C6 C7 C8 N2 -179.8(3) . . . . ?
C2 N2 C8 C3 -0.7(3) . . . . ?
C2 N2 C8 C7 178.7(3) . . . . ?
C15 N4 C9 N3 -0.4(2) . . . . ?
C15 N4 C9 C1 -178.41(18) . . . . ?
C10 N3 C9 N4 0.2(2) . . . . ?
C10 N3 C9 C1 178.31(18) . . . . ?
C2 C1 C9 N4 -51.9(3) . . . . ?
C2 C1 C9 N3 130.30(19) . . . . ?
C9 N3 C10 C11 -178.3(2) . . . . ?
C9 N3 C10 C15 0.0(2) . . . . ?
N3 C10 C11 C12 178.0(2) . . . . ?
C15 C10 C11 C12 -0.1(4) . . . . ?
C10 C11 C12 C13 -0.4(4) . . . . ?
C11 C12 C13 C14 0.5(4) . . . . ?
C12 C13 C14 C15 -0.1(4) . . . . ?
C11 C10 C15 N4 178.2(2) . . . . ?
N3 C10 C15 N4 -0.3(2) . . . . ?
C11 C10 C15 C14 0.5(3) . . . . ?
N3 C10 C15 C14 -178.04(18) . . . . ?
C9 N4 C15 C10 0.4(2) . . . . ?
C9 N4 C15 C14 177.8(2) . . . . ?
C13 C14 C15 C10 -0.4(3) . . . . ?
C13 C14 C15 N4 -177.6(2) . . . . ?
C23 N6 C17 N5 0.0(2) . . . . ?
C23 N6 C17 C16 176.94(18) . . . . ?
C18 N5 C17 N6 0.2(2) . . . . ?
C18 N5 C17 C16 -176.69(18) . . . . ?
C24 C16 C17 N6 126.0(2) . . . . ?
C24 C16 C17 N5 -57.4(2) . . . . ?
C17 N5 C18 C19 177.3(2) . . . . ?
C17 N5 C18 C23 -0.4(2) . . . . ?
N5 C18 C19 C20 -177.3(2) . . . . ?
C23 C18 C19 C20 0.1(3) . . . . ?
C18 C19 C20 C21 -0.5(4) . . . . ?
C19 C20 C21 C22 0.7(4) . . . . ?
C20 C21 C22 C23 -0.6(4) . . . . ?
C17 N6 C23 C18 -0.3(2) . . . . ?
C17 N6 C23 C22 -177.6(2) . . . . ?
C19 C18 C23 N6 -177.57(19) . . . . ?
N5 C18 C23 N6 0.4(2) . . . . ?
C19 C18 C23 C22 0.1(3) . . . . ?
N5 C18 C23 C22 178.0(2) . . . . ?
C21 C22 C23 N6 177.2(2) . . . . ?
C21 C22 C23 C18 0.2(3) . . . . ?
C30 N8 C24 N7 0.3(3) . . . . ?
C30 N8 C24 C16 -179.9(2) . . . . ?
C25 N7 C24 N8 0.0(3) . . . . ?
C25 N7 C24 C16 -179.9(2) . . . . ?
C17 C16 C24 N8 -94.8(2) . . . . ?
C17 C16 C24 N7 85.1(2) . . . . ?
C24 N7 C25 C26 179.8(3) . . . . ?
C24 N7 C25 C30 -0.2(3) . . . . ?
N7 C25 C26 C27 180.0(3) . . . . ?
C30 C25 C26 C27 0.0(5) . . . . ?
C25 C26 C27 C28 -0.8(6) . . . . ?
C26 C27 C28 C29 1.2(6) . . . . ?
C27 C28 C29 C30 -0.8(5) . . . . ?
C26 C25 C30 N8 -179.6(3) . . . . ?
N7 C25 C30 N8 0.4(3) . . . . ?
C26 C25 C30 C29 0.3(4) . . . . ?
N7 C25 C30 C29 -179.7(2) . . . . ?
C24 N8 C30 C25 -0.4(3) . . . . ?
C24 N8 C30 C29 179.7(3) . . . . ?
C28 C29 C30 C25 0.1(4) . . . . ?
C28 C29 C30 N8 180.0(3) . . . . ?
C38 N10 C32 N9 -0.6(3) . . . . ?
C38 N10 C32 C31 177.91(19) . . . . ?
C33 N9 C32 N10 -0.1(2) . . . . ?
C33 N9 C32 C31 -178.65(18) . . . . ?
C39 C31 C32 N10 -83.3(3) . . . . ?
C39 C31 C32 N9 95.0(2) . . . . ?
C32 N9 C33 C38 0.8(2) . . . . ?
C32 N9 C33 C34 179.6(2) . . . . ?
N9 C33 C34 C35 -179.7(2) . . . . ?
C38 C33 C34 C35 -1.0(4) . . . . ?
C33 C34 C35 C36 1.3(4) . . . . ?
C34 C35 C36 C37 -1.0(6) . . . . ?
C35 C36 C37 C38 0.3(6) . . . . ?
N9 C33 C38 C37 179.4(3) . . . . ?
C34 C33 C38 C37 0.4(4) . . . . ?
N9 C33 C38 N10 -1.1(3) . . . . ?
C34 C33 C38 N10 179.9(2) . . . . ?
C36 C37 C38 C33 0.0(5) . . . . ?
C36 C37 C38 N10 -179.4(3) . . . . ?
C32 N10 C38 C33 1.1(3) . . . . ?
C32 N10 C38 C37 -179.5(3) . . . . ?
C45 N12 C39 N11 -0.3(2) . . . . ?
C45 N12 C39 C31 -176.36(19) . . . . ?
C40 N11 C39 N12 0.2(2) . . . . ?
C40 N11 C39 C31 176.26(18) . . . . ?
C32 C31 C39 N12 -134.5(2) . . . . ?
C32 C31 C39 N11 49.9(3) . . . . ?
C39 N11 C40 C41 -178.2(2) . . . . ?
C39 N11 C40 C45 0.0(2) . . . . ?
N11 C40 C41 C42 177.6(2) . . . . ?
C45 C40 C41 C42 -0.4(3) . . . . ?
C40 C41 C42 C43 0.4(4) . . . . ?
C41 C42 C43 C44 -0.2(4) . . . . ?
C42 C43 C44 C45 0.0(4) . . . . ?
N11 C40 C45 N12 -0.2(2) . . . . ?
C41 C40 C45 N12 178.25(19) . . . . ?
N11 C40 C45 C44 -178.3(2) . . . . ?
C41 C40 C45 C44 0.2(3) . . . . ?
C39 N12 C45 C40 0.3(2) . . . . ?
C39 N12 C45 C44 178.2(2) . . . . ?
C43 C44 C45 C40 0.1(4) . . . . ?
C43 C44 C45 N12 -177.6(2) . . . . ?
C53 N14 C47 N13 0.3(2) . . . . ?
C53 N14 C47 C46 -176.83(19) . . . . ?
C48 N13 C47 N14 -0.5(2) . . . . ?
C48 N13 C47 C46 176.67(18) . . . . ?
C54 C46 C47 N14 -133.3(2) . . . . ?
C54 C46 C47 N13 49.8(3) . . . . ?
C47 N13 C48 C49 -177.0(2) . . . . ?
C47 N13 C48 C53 0.5(2) . . . . ?
C53 C48 C49 C50 0.2(3) . . . . ?
N13 C48 C49 C50 177.4(2) . . . . ?
C48 C49 C50 C51 0.5(4) . . . . ?
C49 C50 C51 C52 -0.7(4) . . . . ?
C50 C51 C52 C53 0.2(4) . . . . ?
C51 C52 C53 C48 0.5(4) . . . . ?
C51 C52 C53 N14 -177.3(2) . . . . ?
C49 C48 C53 C52 -0.7(3) . . . . ?
N13 C48 C53 C52 -178.5(2) . . . . ?
C49 C48 C53 N14 177.48(19) . . . . ?
N13 C48 C53 N14 -0.3(2) . . . . ?
C47 N14 C53 C52 177.9(2) . . . . ?
C47 N14 C53 C48 0.0(2) . . . . ?
C60 N16 C54 N15 -0.5(3) . . . . ?
C60 N16 C54 C46 178.1(2) . . . . ?
C55 N15 C54 N16 0.1(2) . . . . ?
C55 N15 C54 C46 -178.55(18) . . . . ?
C47 C46 C54 N16 -80.2(3) . . . . ?
C47 C46 C54 N15 98.3(2) . . . . ?
C54 N15 C55 C60 0.3(2) . . . . ?
C54 N15 C55 C56 179.6(2) . . . . ?
N15 C55 C56 C57 -179.6(2) . . . . ?
C60 C55 C56 C57 -0.3(4) . . . . ?
C55 C56 C57 C58 1.2(5) . . . . ?
C56 C57 C58 C59 -1.4(6) . . . . ?
C57 C58 C59 C60 0.7(6) . . . . ?
N15 C55 C60 C59 179.1(3) . . . . ?
C56 C55 C60 C59 -0.3(4) . . . . ?
N15 C55 C60 N16 -0.6(3) . . . . ?
C56 C55 C60 N16 180.0(2) . . . . ?
C58 C59 C60 C55 0.1(5) . . . . ?
C58 C59 C60 N16 179.8(3) . . . . ?
C54 N16 C60 C55 0.7(3) . . . . ?
C54 N16 C60 C59 -179.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H3 N6 . . 4_565 2.795(2) 0.99(2) 1.80(2) 175(2) no
N3 H8 N8 . . 4_565 2.773(2) 1.02(2) 1.77(2) 166(2) no
N5 H15 N2 . . . 2.799(2) 0.93(2) 1.90(2) 163(2) no
N7 H20 N4 . . . 2.852(2) 1.00(3) 1.86(3) 170(3) no
N9 H27 N12 . . 3_556 2.789(3) 0.95(3) 1.85(3) 175(2) no
N11 H32 N16 . . . 2.826(3) 0.95(3) 1.91(3) 160(2) no
N13 H39 N10 . . . 2.809(3) 0.97(3) 1.88(3) 161(2) no
N15 H44 N14 . . 3_656 2.793(3) 0.92(3) 1.88(3) 172(2) no

# start Validation Reply Form
_vrf_PLAT110_BI2C-b              
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ...          ? Check 
RESPONSE: Symmetry is actually broken by the hydrogen locations. 
;
_vrf_PLAT112_BI2C-b              
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem        41        100 %Fit  
RESPONSE: Symmetry is actually broken by the hydrogen locations.
;
_vrf_PLAT113_BI2C-b              
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group      I41/a Check 
RESPONSE: Symmetry is actually broken by the hydrogen locations and 
          confimed by the breaking of systematic absences.  
;
_vrf_PLAT910_BI2C-b              
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         18 Note  
RESPONSE: ...
;
# end Validation Reply Form
#==============================================================================
# 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
#==============================================================================
_chemical_name_systematic        bis-(1H-benzimidazol-2-yl)-methane
_exptl_crystal_recrystallization_method Sublimation
