# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_b
_audit_block_doi                 10.5517/ccdc.csd.cc25llzc
_database_code_depnum_ccdc_archive 'CCDC 2013883'
loop_
_audit_author_name
_audit_author_address
'Li Jie'
;State Key Laboratory of Chemical Engineering, Tianjin University
China
;
_audit_update_record             
;
2020-07-03 deposited with the CCDC.	2022-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        Phenanthrene-1,2,4,5-tetracyanobenzene
_chemical_name_common            Phenanthrene-TCNB
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H10 ,C10H2N4'
_chemical_formula_sum            'C24 H12 N4'
_chemical_formula_weight         354.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   'C2/m (12)'

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

_cell_length_a                   9.4224(19)
_cell_length_b                   13.085(3)
_cell_length_c                   7.2610(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.95(3)
_cell_angle_gamma                90.00
_cell_volume                     894.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             364
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9801
_exptl_absorpt_correction_T_max  0.9880
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3721
_diffrn_reflns_av_R_equivalents  0.0700
_diffrn_reflns_av_sigmaI/netI    0.0625
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         25.49
_reflns_number_total             872
_reflns_number_gt                530
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1700P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.008(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         872
_refine_ls_number_parameters     73
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1309
_refine_ls_R_factor_gt           0.0819
_refine_ls_wR_factor_ref         0.2761
_refine_ls_wR_factor_gt          0.2413
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0000 -0.1054(3) 1.0000 0.0553(13) Uani 1 2 d S . .
H1A H 1.0000 -0.1764 1.0000 0.066 Uiso 1 2 calc SR . .
C2 C 0.8769(3) -0.0535(2) 0.9485(4) 0.0507(10) Uani 1 1 d . . .
C3 C 0.7489(4) -0.1095(3) 0.8965(5) 0.0625(11) Uani 1 1 d . . .
N1 N 0.6483(3) -0.1553(3) 0.8558(5) 0.0855(13) Uani 1 1 d . . .
C8 C 0.0734(7) 0.0000 0.5362(8) 0.129(4) Uani 1 2 d S . .
C6 C 0.1482(5) 0.0904(6) 0.5719(6) 0.120(2) Uani 1 1 d . . .
C7 C 0.0701(10) 0.1600(5) 0.5338(10) 0.071(2) Uani 0.50 1 d P . .
H7A H 0.1097 0.2245 0.5526 0.085 Uiso 0.50 1 calc PR . .
C5 C 0.2889(5) 0.0904(7) 0.6400(6) 0.124(2) Uani 1 1 d . . .
H5A H 0.3358 0.1520 0.6626 0.149 Uiso 1 1 calc R . .
C4 C 0.3585(9) 0.0000 0.6739(10) 0.134(4) Uani 1 2 d S . .
H4A H 0.4526 0.0000 0.7197 0.161 Uiso 1 2 calc SR . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.378(4) 2_757 ?
C1 C2 1.378(4) . ?
C1 H1A 0.9300 . ?
C2 C2 1.400(6) 6 ?
C2 C3 1.445(4) . ?
C3 N1 1.147(4) . ?
C8 C6 1.395(7) . ?
C8 C6 1.395(7) 6 ?
C8 C8 1.455(14) 5_556 ?
C6 C7 1.194(9) . ?
C6 C5 1.391(6) . ?
C7 C7 1.386(18) 2_556 ?
C7 H7A 0.9300 . ?
C5 C4 1.369(8) . ?
C5 H5A 0.9300 . ?
C4 C5 1.369(8) 6 ?
C4 H4A 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 C1 C2 121.0(4) 2_757 . ?
C2 C1 H1A 119.5 2_757 . ?
C2 C1 H1A 119.5 . . ?
C1 C2 C2 119.5(2) . 6 ?
C1 C2 C3 120.1(3) . . ?
C2 C2 C3 120.46(17) 6 . ?
N1 C3 C2 179.0(3) . . ?
C6 C8 C6 116.1(7) . 6 ?
C6 C8 C8 122.0(4) . 5_556 ?
C6 C8 C8 122.0(4) 6 5_556 ?
C7 C6 C5 130.4(9) . . ?
C7 C6 C8 107.7(5) . . ?
C5 C6 C8 121.9(8) . . ?
C6 C7 C7 130.3(5) . 2_556 ?
C6 C7 H7A 114.8 . . ?
C7 C7 H7A 114.8 2_556 . ?
C4 C5 C6 120.3(8) . . ?
C4 C5 H5A 119.9 . . ?
C6 C5 H5A 119.9 . . ?
C5 C4 C5 119.5(8) 6 . ?
C5 C4 H4A 120.2 6 . ?
C5 C4 H4A 120.2 . . ?

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
C2 C1 C2 C2 0.0 2_757 . . 6 ?
C2 C1 C2 C3 -179.5(3) 2_757 . . . ?
C1 C2 C3 N1 3(22) . . . . ?
C2 C2 C3 N1 -176(100) 6 . . . ?
C6 C8 C6 C7 179.7(5) 6 . . . ?
C8 C8 C6 C7 0.5(10) 5_556 . . . ?
C6 C8 C6 C5 -0.3(9) 6 . . . ?
C8 C8 C6 C5 -179.5(6) 5_556 . . . ?
C5 C6 C7 C7 -179.9(8) . . . 2_556 ?
C8 C6 C7 C7 0.0(13) . . . 2_556 ?
C7 C6 C5 C4 -179.9(7) . . . . ?
C8 C6 C5 C4 0.1(8) . . . . ?
C6 C5 C4 C5 0.1(10) . . . 6 ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.043
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeCN'
####################################################################### 
# 
# 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_DBS-TCNB-b
_database_code_depnum_ccdc_archive 'CCDC 2056561'
loop_
_audit_author_name
_audit_author_address
'Li Jie'
;State Key Laboratory of Chemical Engineering, Tianjin University
China
;
_audit_update_record             
;
2021-03-17 deposited with the CCDC.	2022-05-06 downloaded from the CCDC.
;
_audit_creation_date             2021-01-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H2 N4, 2.5(C4.81 H3.21 Se0.4)'
_chemical_formula_sum            'C22 H10 N4 Se'
_chemical_formula_weight         409.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   9.3536(6)
_cell_length_b                   12.7325(8)
_cell_length_c                   14.2952(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.816(6)
_cell_angle_gamma                90
_cell_volume                     1700.43(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3327
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.8350
_cell_measurement_theta_min      2.7090
_shelx_estimated_absorpt_T_max   0.690
_shelx_estimated_absorpt_T_min   0.641
_exptl_absorpt_coefficient_mu    2.222
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7366
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         2.143
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00    4.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  35.00   1.00    4.00    --  -25.00  45.00  90.00  150
  3  ω   -115.00   5.00   1.00    4.00    --  -25.00  45.00 180.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0243846000
_diffrn_orient_matrix_UB_12      -0.0324454000
_diffrn_orient_matrix_UB_13      -0.0363255000
_diffrn_orient_matrix_UB_21      0.0719047000
_diffrn_orient_matrix_UB_22      0.0107720000
_diffrn_orient_matrix_UB_23      0.0150329000
_diffrn_orient_matrix_UB_31      -0.0004440000
_diffrn_orient_matrix_UB_32      -0.0439543000
_diffrn_orient_matrix_UB_33      0.0303968000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1371
_reflns_number_total             1740
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       CrystalClear(Rigaku,2008)
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.0061(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         1740
_refine_ls_number_restraints     240
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0468
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0281P)²+4.5822P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1124
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Se1 \\sim C6 \\sim C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim Se1A \\sim C1A
\\sim C2A \\sim C3A \\sim C4A \\sim C5A \\sim C6A: within 1.7A with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(Se1) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C2) \\sim
Ueq, Uanis(C3) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(Se1A)
\\sim Ueq, Uanis(C1A) \\sim Ueq, Uanis(C2A) \\sim Ueq, Uanis(C3A) \\sim Ueq,
Uanis(C4A) \\sim Ueq, Uanis(C5A) \\sim Ueq, Uanis(C6A) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
3. Others
 Sof(C1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(H3A)=Sof(C4A)=Sof(H4A)=Sof(C5A)=
 Sof(H5A)=Sof(C6A)=1-FVAR(1)
 Sof(Se1A)=0.5*(1-FVAR(2))
 Sof(Se1)=0.5*FVAR(2)
 Sof(C6)=Sof(C1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(H4)=Sof(C5)=
 Sof(H5)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C2(H2), C3(H3), C4(H4), C5(H5), C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A)
4.b Fitted hexagon refined as free rotating group:
 C6(C1,C2,C3,C4,C5), C1A(C2A,C3A,C4A,C5A,C6A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 1.1016(3) 0.4091(2) 0.32622(18) 0.0337(6) Uani 1 1 d . . . . .
N2 N 0.3962(3) 0.4077(2) 0.17534(18) 0.0342(6) Uani 1 1 d . . . . .
C7 C 0.4970(3) 0.3618(2) 0.1968(2) 0.0245(6) Uani 1 1 d . . . . .
C8 C 0.6259(3) 0.3044(2) 0.22369(18) 0.0206(6) Uani 1 1 d . . . . .
C9 C 0.7493(3) 0.3601(2) 0.25030(19) 0.0230(6) Uani 1 1 d . . . . .
H9 H 0.748620 0.434710 0.250566 0.028 Uiso 1 1 calc R . . . .
C10 C 0.8732(3) 0.3056(2) 0.27643(18) 0.0209(6) Uani 1 1 d . . . . .
C11 C 1.0017(3) 0.3629(2) 0.3042(2) 0.0251(6) Uani 1 1 d . . . . .
Se1 Se 0.750000 0.07575(9) 0.500000 0.0344(4) Uani 0.4006(13) 2 d S TU P A 1
C6 C 0.6749(4) 0.2795(5) 0.4813(4) 0.0237(16) Uani 0.4006(13) 1 d . U . A 1
C1 C 0.6177(6) 0.1795(4) 0.4684(4) 0.0253(17) Uani 0.4006(13) 1 d G U . A 1
C2 C 0.4768(7) 0.1674(5) 0.4347(7) 0.0314(17) Uani 0.4006(13) 1 d G U . A 1
H2 H 0.437657 0.099045 0.425956 0.038 Uiso 0.4006(13) 1 calc R . . A 1
C3 C 0.3930(6) 0.2553(6) 0.4138(9) 0.032(2) Uani 0.4006(13) 1 d G U . A 1
H3 H 0.296711 0.247007 0.390733 0.039 Uiso 0.4006(13) 1 calc R . . A 1
C4 C 0.4503(7) 0.3553(5) 0.4266(8) 0.0304(18) Uani 0.4006(13) 1 d G U . A 1
H4 H 0.393050 0.415378 0.412298 0.037 Uiso 0.4006(13) 1 calc R . . A 1
C5 C 0.5912(6) 0.3674(4) 0.4603(4) 0.0288(17) Uani 0.4006(13) 1 d G U . A 1
H5 H 0.630335 0.435788 0.469088 0.035 Uiso 0.4006(13) 1 calc R . . A 1
Se1A Se 0.750000 0.42398(5) 0.500000 0.0272(3) Uani 0.5994(13) 2 d S TU P A 2
C1A C 0.6199(4) 0.3160(3) 0.4686(3) 0.0214(11) Uani 0.5994(13) 1 d . U . A 2
C2A C 0.4798(5) 0.3298(3) 0.4337(5) 0.0300(13) Uani 0.5994(13) 1 d G U . A 2
H2A H 0.442235 0.398545 0.424923 0.036 Uiso 0.5994(13) 1 calc R . . A 2
C3A C 0.3948(4) 0.2428(4) 0.4118(6) 0.0334(15) Uani 0.5994(13) 1 d G U . A 2
H3A H 0.299026 0.252219 0.387926 0.040 Uiso 0.5994(13) 1 calc R . . A 2
C4A C 0.4498(4) 0.1422(3) 0.4247(5) 0.0295(13) Uani 0.5994(13) 1 d G U . A 2
H4A H 0.391662 0.082770 0.409636 0.035 Uiso 0.5994(13) 1 calc R . . A 2
C5A C 0.5899(4) 0.1284(2) 0.4595(3) 0.0247(11) Uani 0.5994(13) 1 d G U . A 2
H5A H 0.627508 0.059645 0.468344 0.030 Uiso 0.5994(13) 1 calc R . . A 2
C6A C 0.6750(3) 0.2154(3) 0.4815(2) 0.0171(10) Uani 0.5994(13) 1 d G U . A 2


_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 C11 1.136(4) . ?
N2 C7 1.139(4) . ?
C7 C8 1.445(4) . ?
C8 C9 1.392(4) . ?
C8 C10 1.400(4) 7_655 ?
C9 H9 0.9500 . ?
C9 C10 1.387(4) . ?
C10 C11 1.445(4) . ?
Se1 C1 1.851(5) . ?
Se1 C1 1.851(7) 2_656 ?
C6 C6 1.478(7) 2_656 ?
C6 C1 1.3900 . ?
C6 C5 1.3900 . ?
C1 C2 1.3900 . ?
C2 H2 0.9500 . ?
C2 C3 1.3900 . ?
C3 H3 0.9500 . ?
C3 C4 1.3900 . ?
C4 H4 0.9500 . ?
C4 C5 1.3900 . ?
C5 H5 0.9500 . ?
Se1A C1A 1.875(3) 2_656 ?
Se1A C1A 1.875(3) . ?
C1A C2A 1.3900 . ?
C1A C6A 1.3900 . ?
C2A H2A 0.9500 . ?
C2A C3A 1.3900 . ?
C3A H3A 0.9500 . ?
C3A C4A 1.3900 . ?
C4A H4A 0.9500 . ?
C4A C5A 1.3900 . ?
C5A H5A 0.9500 . ?
C5A C6A 1.3900 . ?
C6A C6A 1.475(5) 2_656 ?

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
N2 C7 C8 179.4(3) . . ?
C9 C8 C7 119.0(3) . . ?
C9 C8 C10 120.3(3) . 7_655 ?
C10 C8 C7 120.7(3) 7_655 . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.3(3) . . ?
C10 C9 H9 120.3 . . ?
C8 C10 C11 120.0(3) 7_655 . ?
C9 C10 C8 120.4(3) . 7_655 ?
C9 C10 C11 119.6(3) . . ?
N1 C11 C10 179.1(3) . . ?
C1 Se1 C1 88.9(6) 2_656 . ?
C1 C6 C6 113.6(2) . 2_656 ?
C1 C6 C5 120.0 . . ?
C5 C6 C6 126.4(2) . 2_656 ?
C6 C1 Se1 111.9(4) . . ?
C6 C1 C2 120.0 . . ?
C2 C1 Se1 128.1(4) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C2A C1A Se1A 125.6(2) . . ?
C2A C1A C6A 120.0 . . ?
C6A C1A Se1A 114.4(2) . . ?
C1A C2A H2A 120.0 . . ?
C3A C2A C1A 120.0 . . ?
C3A C2A H2A 120.0 . . ?
C2A C3A H3A 120.0 . . ?
C2A C3A C4A 120.0 . . ?
C4A C3A H3A 120.0 . . ?
C3A C4A H4A 120.0 . . ?
C3A C4A C5A 120.0 . . ?
C5A C4A H4A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C6A C5A C4A 120.0 . . ?
C6A C5A H5A 120.0 . . ?
C1A C6A C6A 112.8 . 2_656 ?
C5A C6A C1A 120.0 . . ?
C5A C6A C6A 127.2 . 2_656 ?

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 C8 C9 C10 179.8(2) . . . . ?
C8 C9 C10 C8 -0.2(5) . . . 7_655 ?
C8 C9 C10 C11 -179.9(2) . . . . ?
C10 C8 C9 C10 0.2(5) 7_655 . . . ?
Se1 C1 C2 C3 -179.4(5) . . . . ?
C6 C6 C1 Se1 -1.4(6) 2_656 . . . ?
C6 C6 C1 C2 179.2(8) 2_656 . . . ?
C6 C6 C5 C4 -179.1(9) 2_656 . . . ?
C6 C1 C2 C3 0.0 . . . . ?
C1 Se1 C1 C6 0.5(7) 2_656 . . . ?
C1 Se1 C1 C2 179.9(10) 2_656 . . . ?
C1 C6 C5 C4 0.0 . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C5 C6 C1 Se1 179.5(5) . . . . ?
C5 C6 C1 C2 0.0 . . . . ?
Se1A C1A C2A C3A 179.0(3) . . . . ?
Se1A C1A C6A C5A -179.1(3) . . . . ?
Se1A C1A C6A C6A 0.6(6) . . . 2_656 ?
C1A Se1A C1A C2A -179.3(4) 2_656 . . . ?
C1A Se1A C1A C6A -0.24(15) 2_656 . . . ?
C1A C2A C3A C4A 0.0 . . . . ?
C2A C1A C6A C5A 0.0 . . . . ?
C2A C1A C6A C6A 179.7(8) . . . 2_656 ?
C2A C3A C4A C5A 0.0 . . . . ?
C3A C4A C5A C6A 0.0 . . . . ?
C4A C5A C6A C1A 0.0 . . . . ?
C4A C5A C6A C6A -179.7(9) . . . 2_656 ?
C6A C1A C2A C3A 0.0 . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.329
_oxdiff_exptl_absorpt_empirical_full_min 0.836
####################################################################### 
# 
# 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_CBZ-TCNB-b
_audit_block_doi                 10.5517/ccdc.csd.cc2419zh
_database_code_depnum_ccdc_archive 'CCDC 1967476'
loop_
_audit_author_name
_audit_author_address
'Li Jie'
;State Key Laboratory of Chemical Engineering, Tianjin University
China
;
_audit_update_record             
;
2021-03-17 deposited with the CCDC.	2022-05-06 downloaded from the CCDC.
;
_audit_creation_date             2020-03-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H2 N4, 2(C6 H4.5 N0.5)'
_chemical_formula_sum            'C22 H11 N5'
_chemical_formula_weight         345.36
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   9.4658(19)
_cell_length_b                   12.597(3)
_cell_length_c                   7.1429(14)
_cell_angle_alpha                90
_cell_angle_beta                 94.21(3)
_cell_angle_gamma                90
_cell_volume                     849.4(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1910
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      3.24
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9857
_exptl_absorpt_correction_T_min  0.9764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4232
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.477
_diffrn_reflns_theta_min         3.234
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.901
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                1056
_reflns_number_total             1941
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.106
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 
;
 Flack x determined using 321 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   4.3(10)
_refine_ls_extinction_coef       0.008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1941
_refine_ls_number_restraints     112
_refine_ls_R_factor_all          0.1263
_refine_ls_R_factor_gt           0.0617
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0474P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1158
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 N3'-C12'
 2.11 with sigma of 0.01
 N3-C7 = N3'-C11'
 1.38 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(N1) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C12') \\sim Ueq, Uanis(N2)
\\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C10) \\sim Ueq: with
sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(N3) \\sim Ueq, Uanis(N3') \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C9) \\sim
Ueq, Uanis(C11) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C7') \\sim Ueq,
Uanis(C8') \\sim Ueq, Uanis(C9') \\sim Ueq, Uanis(C10') \\sim Ueq, Uanis(C11')
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: N3(0.25) H3(0.25) C7(0.5) C8(0.5) H8(0.5) C9(0.5) H9(0.5) C10(0.5)
 H10(0.5) C11(0.5) H11(0.5) C12(0.5) N3'(0.25) H3'(0.25) C7'(0.5) H7'(0.5)
 C8'(0.5) H8'(0.5) C9'(0.5) H9'(0.5) C10'(0.5) H10'(0.5) C11'(0.5) C12'(0.5)
5.a Riding coordinates:
 C7'(H7'), C8'(H8'), C9'(H9'), C10'(H10')
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), N3(H3), C8(H8), C9(H9), C10(H10), C11(H11), N3'(H3')
5.c Fitted hexagon refined as free rotating group:
 C7(C8,C9,C10,C11,C12)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6500(7) 0.2805(5) 0.8454(13) 0.074(2) Uani 1 1 d . U . . .
N2 N 0.6498(8) -0.0368(6) 0.8479(15) 0.089(3) Uani 1 1 d . U . . .
C1 C 0.7535(10) 0.2320(6) 0.8925(15) 0.064(2) Uani 1 1 d . U . . .
C2 C 0.8751(7) 0.1739(5) 0.9455(11) 0.0486(19) Uani 1 1 d . . . . .
C3 C 1.000000 0.2286(7) 1.000000 0.059(3) Uani 1 2 d S T P . .
H3A H 0.999999 0.302399 1.000003 0.071 Uiso 1 2 calc RS T P . .
C4 C 1.000000 0.0074(8) 1.000000 0.049(3) Uani 1 2 d S T P . .
H4 H 0.999999 -0.066386 0.999998 0.058 Uiso 1 2 calc RS T P . .
C5 C 0.8794(8) 0.0632(5) 0.9478(10) 0.0478(18) Uani 1 1 d . . . . .
C6 C 0.7474(8) 0.0069(5) 0.8895(14) 0.0534(18) Uani 1 1 d . U . . .
N3 N 0.000000 -0.0224(11) 0.500000 0.080(6) Uani 0.5 2 d DS TU P A 1
H3 H 0.000000 -0.090630 0.499999 0.096 Uiso 0.5 2 calc RS T P A 1
C7 C 0.1131(14) 0.0431(9) 0.550(2) 0.055(4) Uani 0.5 1 d D U . A 1
C8 C 0.2507(16) 0.0187(9) 0.617(2) 0.116(13) Uani 0.5 1 d G U . A 1
H8 H 0.278796 -0.051806 0.630055 0.139 Uiso 0.5 1 calc R . . A 1
C9 C 0.3463(10) 0.0997(15) 0.665(2) 0.058(5) Uani 0.5 1 d G U . A 1
H9 H 0.438353 0.083337 0.710533 0.069 Uiso 0.5 1 calc R . . A 1
C10 C 0.3043(14) 0.2051(12) 0.646(2) 0.084(8) Uani 0.5 1 d G U . A 1
H10 H 0.368223 0.259256 0.678273 0.100 Uiso 0.5 1 calc R . . A 1
C11 C 0.1666(17) 0.2295(8) 0.578(2) 0.068(5) Uani 0.5 1 d G U . A 1
H11 H 0.138535 0.300033 0.565535 0.082 Uiso 0.5 1 calc R . . A 1
C12 C 0.0710(10) 0.1485(11) 0.530(2) 0.055(4) Uani 0.5 1 d G U . A 1
N3' N 0.000000 0.2466(12) 0.500000 0.096(7) Uani 0.5 2 d DS TU P B 2
H3' H 0.000001 0.314916 0.499999 0.115 Uiso 0.5 2 calc RS T P B 2
C7' C 0.172(2) -0.0009(14) 0.584(2) 0.067(4) Uani 0.5 1 d . U . B 2
H7' H 0.152303 -0.073290 0.577249 0.080 Uiso 0.5 1 d R . . B 2
C8' C 0.3032(16) 0.0353(14) 0.644(2) 0.055(4) Uani 0.5 1 d . U . B 2
H8' H 0.373223 -0.013579 0.682215 0.066 Uiso 0.5 1 d R . . B 2
C9' C 0.3390(16) 0.151(2) 0.655(3) 0.076(6) Uani 0.5 1 d . U . B 2
H9' H 0.428260 0.174705 0.699852 0.091 Uiso 0.5 1 d R . . B 2
C10' C 0.246(2) 0.2283(17) 0.619(3) 0.096(7) Uani 0.5 1 d . U . B 2
H10' H 0.265702 0.300616 0.625827 0.115 Uiso 0.5 1 d R . . B 2
C11' C 0.1153(17) 0.1867(15) 0.555(3) 0.071(6) Uani 0.5 1 d D U . B 2
C12' C 0.0745(15) 0.0867(12) 0.541(3) 0.052(4) Uani 0.5 1 d D U . B 2


_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 1.183(10) . ?
N2 C6 1.097(9) . ?
C1 C2 1.393(12) . ?
C2 C3 1.399(8) . ?
C2 C5 1.395(4) . ?
C3 H3A 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.369(9) . ?
C4 C5 1.369(9) 2_757 ?
C5 C6 1.470(10) . ?
N3 H3 0.8600 . ?
N3 C7 1.377(10) . ?
N3 C7 1.377(10) 2_556 ?
C7 C8 1.3900 . ?
C7 C12 1.3900 . ?
C8 H8 0.9300 . ?
C8 C9 1.3900 . ?
C9 H9 0.9300 . ?
C9 C10 1.3900 . ?
C10 H10 0.9300 . ?
C10 C11 1.3900 . ?
C11 H11 0.9300 . ?
C11 C12 1.3900 . ?
C12 C12 1.382(17) 2_556 ?
N3' H3' 0.8600 . ?
N3' C11' 1.360(13) . ?
N3' C11' 1.360(13) 2_556 ?
C7' H7' 0.9301 . ?
C7' C8' 1.37(2) . ?
C7' C12' 1.455(19) . ?
C8' H8' 0.9301 . ?
C8' C9' 1.50(3) . ?
C9' H9' 0.9300 . ?
C9' C10' 1.32(3) . ?
C10' H10' 0.9297 . ?
C10' C11' 1.39(2) . ?
C11' C12' 1.319(16) . ?
C12' C12' 1.49(3) 2_556 ?

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
N1 C1 C2 179.1(10) . . ?
C1 C2 C3 118.8(6) . . ?
C1 C2 C5 123.4(8) . . ?
C5 C2 C3 117.8(8) . . ?
C2 C3 C2 120.9(8) . 2_757 ?
C2 C3 H3A 119.5 . . ?
C2 C3 H3A 119.5 2_757 . ?
C5 C4 H4 120.9 2_757 . ?
C5 C4 H4 120.9 . . ?
C5 C4 C5 118.3(8) 2_757 . ?
C2 C5 C6 117.1(7) . . ?
C4 C5 C2 122.6(8) . . ?
C4 C5 C6 120.3(6) . . ?
N2 C6 C5 178.7(9) . . ?
C7 N3 H3 126.8 2_556 . ?
C7 N3 H3 126.8 . . ?
C7 N3 C7 106.4(15) . 2_556 ?
N3 C7 C8 130.4(12) . . ?
N3 C7 C12 109.6(12) . . ?
C8 C7 C12 120.0 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C7 120.0 . . ?
C12 C12 C7 107.2 2_556 . ?
C12 C12 C11 132.71(11) 2_556 . ?
C11' N3' H3' 123.7 . . ?
C11' N3' H3' 123.7 2_556 . ?
C11' N3' C11' 112.6(18) 2_556 . ?
C8' C7' H7' 121.0 . . ?
C8' C7' C12' 111.1(14) . . ?
C12' C7' H7' 127.9 . . ?
C7' C8' H8' 119.0 . . ?
C7' C8' C9' 122.6(15) . . ?
C9' C8' H8' 118.5 . . ?
C8' C9' H9' 121.5 . . ?
C10' C9' C8' 124.2(15) . . ?
C10' C9' H9' 114.0 . . ?
C9' C10' H10' 125.8 . . ?
C9' C10' C11' 110.5(19) . . ?
C11' C10' H10' 123.5 . . ?
N3' C11' C10' 124.2(17) . . ?
C12' C11' N3' 106.5(14) . . ?
C12' C11' C10' 129.2(15) . . ?
C7' C12' C12' 130.5(10) . 2_556 ?
C11' C12' C7' 122.1(13) . . ?
C11' C12' C12' 107.0(9) . 2_556 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C2 180.0(9) . . . 2_757 ?
C1 C2 C5 C4 179.9(5) . . . . ?
C1 C2 C5 C6 0.4(18) . . . . ?
C3 C2 C5 C4 -0.3(14) . . . . ?
C3 C2 C5 C6 -179.8(5) . . . . ?
C5 C2 C3 C2 0.1(7) . . . 2_757 ?
C5 C4 C5 C2 0.1(7) 2_757 . . . ?
C5 C4 C5 C6 179.7(9) 2_757 . . . ?
N3 C7 C8 C9 -177.4(15) . . . . ?
N3 C7 C12 C11 177.9(12) . . . . ?
N3 C7 C12 C12 0.7(16) . . . 2_556 ?
C7 N3 C7 C8 177.3(15) 2_556 . . . ?
C7 N3 C7 C12 -0.3(5) 2_556 . . . ?
C7 C8 C9 C10 0.0 . . . . ?
C8 C7 C12 C11 0.0 . . . . ?
C8 C7 C12 C12 -177(2) . . . 2_556 ?
C8 C9 C10 C11 0.0 . . . . ?
C9 C10 C11 C12 0.0 . . . . ?
C10 C11 C12 C7 0.0 . . . . ?
C10 C11 C12 C12 176(3) . . . 2_556 ?
C12 C7 C8 C9 0.0 . . . . ?
N3' C11' C12' C7' 178.5(18) . . . . ?
N3' C11' C12' C12' 4(3) . . . 2_556 ?
C7' C8' C9' C10' 4(2) . . . . ?
C8' C7' C12' C11' 2(3) . . . . ?
C8' C7' C12' C12' 175(3) . . . 2_556 ?
C8' C9' C10' C11' -5(2) . . . . ?
C9' C10' C11' N3' -178(2) . . . . ?
C9' C10' C11' C12' 5(3) . . . . ?
C10' C11' C12' C7' -4(4) . . . . ?
C10' C11' C12' C12' -178(2) . . . 2_556 ?
C11' N3' C11' C10' -179(3) 2_556 . . . ?
C11' N3' C11' C12' -1.9(11) 2_556 . . . ?
C12' C7' C8' C9' -2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_BPE-TCNB-hb
_audit_block_doi                 10.5517/ccdc.csd.cc25qnzk
_database_code_depnum_ccdc_archive 'CCDC 2017789'
loop_
_audit_author_name
_audit_author_address
'Li Jie'
;State Key Laboratory of Chemical Engineering, Tianjin University
China
;
_audit_update_record             
;
2021-03-17 deposited with the CCDC.	2022-05-06 downloaded from the CCDC.
;
_audit_creation_date             2020-07-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H10 N2, C10 H2 N4'
_chemical_formula_sum            'C22 H12 N6'
_chemical_formula_weight         360.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   21.7837(14)
_cell_length_b                   6.1020(4)
_cell_length_c                   14.1705(8)
_cell_angle_alpha                90
_cell_angle_beta                 104.831(6)
_cell_angle_gamma                90
_cell_volume                     1820.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5104
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      32.5150
_cell_measurement_theta_min      1.9780
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9080
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.363
_diffrn_reflns_theta_min         3.105
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00    6.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  65.00   1.00    6.00    --  -25.00  45.00  90.00  180
  3  ω   -115.00  65.00   1.00    6.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0127589000
_diffrn_orient_matrix_UB_12      -0.0213974000
_diffrn_orient_matrix_UB_13      0.0403662000
_diffrn_orient_matrix_UB_21      0.0301102000
_diffrn_orient_matrix_UB_22      0.0209442000
_diffrn_orient_matrix_UB_23      0.0323909000
_diffrn_orient_matrix_UB_31      -0.0080695000
_diffrn_orient_matrix_UB_32      0.1123357000
_diffrn_orient_matrix_UB_33      0.0016320000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1556
_reflns_number_total             1859
_reflns_odcompleteness_completeness 99.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       CrystalClear(Rigaku,2008)
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1859
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0472
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0631P)²+1.4463P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1288
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 C3, C4
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3. Uiso/Uaniso restraints and constraints
C6 \\sim C6A: within 1.7A with sigma of 0.01 and sigma for terminal atoms of
0.02
Uanis(C6) \\sim Ueq, Uanis(C6A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Sof(C6A)=Sof(H6A)=1-FVAR(1)
 Sof(C6)=Sof(H6)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C6A(H6A), C7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.37845(6) 0.6308(2) 0.52154(10) 0.0287(3) Uani 1 1 d . . . . .
C1 C 0.42521(8) 0.5735(3) 0.59851(13) 0.0340(4) Uani 1 1 d . . . . .
H1 H 0.432166 0.662499 0.655275 0.041 Uiso 1 1 calc R . . . .
C2 C 0.46390(8) 0.3951(3) 0.60135(14) 0.0390(4) Uani 1 1 d . . . . .
H2 H 0.496455 0.364681 0.658677 0.047 Uiso 1 1 calc R . . . .
C3 C 0.45571(8) 0.2608(3) 0.52174(15) 0.0400(5) Uani 1 1 d . U . . .
C4 C 0.40713(9) 0.3174(3) 0.43931(14) 0.0394(5) Uani 1 1 d . U . . .
H4 H 0.399298 0.230251 0.381908 0.047 Uiso 1 1 calc R . . . .
C5 C 0.37056(7) 0.5030(3) 0.44281(12) 0.0318(4) Uani 1 1 d . . . . .
H5 H 0.338276 0.540645 0.386182 0.038 Uiso 1 1 calc R . . . .
C6 C 0.50104(11) 0.0739(4) 0.53444(17) 0.0251(8) Uani 0.757(8) 1 d . U P A 1
H6 H 0.532642 0.060333 0.594363 0.030 Uiso 0.757(8) 1 calc R . P A 1
C6A C 0.4741(4) 0.0483(13) 0.4710(5) 0.023(2) Uani 0.243(8) 1 d . U P A 2
H6A H 0.451851 -0.003907 0.408472 0.028 Uiso 0.243(8) 1 calc R . P A 2
N2 N 0.38070(7) 0.1197(3) 0.74605(10) 0.0371(4) Uani 1 1 d . . . . .
N3 N 0.27697(7) 0.6797(2) 0.71790(10) 0.0329(4) Uani 1 1 d . . . . .
C7 C 0.21369(6) 0.4433(2) 0.49022(10) 0.0204(3) Uani 1 1 d . . . . .
H7 H 0.189126 0.573677 0.483745 0.024 Uiso 1 1 calc R . . . .
C8 C 0.25884(6) 0.3973(2) 0.57730(10) 0.0198(3) Uani 1 1 d . . . . .
C9 C 0.29491(6) 0.2039(2) 0.58692(10) 0.0198(3) Uani 1 1 d . . . . .
C10 C 0.34231(7) 0.1575(2) 0.67627(10) 0.0242(3) Uani 1 1 d . . . . .
C11 C 0.26873(7) 0.5530(2) 0.65624(10) 0.0235(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.334(2) . ?
N1 C5 1.336(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.371(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.369(3) . ?
C3 C4 1.404(3) . ?
C3 C6 1.489(3) . ?
C3 C6A 1.583(8) . ?
C4 H4 0.9500 . ?
C4 C5 1.393(2) . ?
C5 H5 0.9500 . ?
C6 C6 1.321(5) 5_656 ?
C6 H6 0.9500 . ?
C6A C6A 1.348(16) 5_656 ?
C6A H6A 0.9500 . ?
N2 C10 1.1433(19) . ?
N3 C11 1.146(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.3955(19) . ?
C7 C9 1.390(2) 7_556 ?
C8 C9 1.405(2) . ?
C8 C11 1.441(2) . ?
C9 C10 1.4422(19) . ?

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 C5 115.96(14) . . ?
N1 C1 H1 117.7 . . ?
N1 C1 C2 124.54(17) . . ?
C2 C1 H1 117.7 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.12(17) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C4 116.74(16) . . ?
C2 C3 C6 114.61(18) . . ?
C2 C3 C6A 150.4(3) . . ?
C4 C3 C6 128.63(19) . . ?
C4 C3 C6A 92.8(3) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.12(17) . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 123.51(16) . . ?
N1 C5 H5 118.2 . . ?
C4 C5 H5 118.2 . . ?
C3 C6 H6 118.8 . . ?
C6 C6 C3 122.5(3) 5_656 . ?
C6 C6 H6 118.8 5_656 . ?
C3 C6A H6A 124.7 . . ?
C6A C6A C3 110.6(7) 5_656 . ?
C6A C6A H6A 124.7 5_656 . ?
C8 C7 H7 120.4 . . ?
C9 C7 H7 120.4 7_556 . ?
C9 C7 C8 119.20(13) 7_556 . ?
C7 C8 C9 120.33(13) . . ?
C7 C8 C11 119.01(13) . . ?
C9 C8 C11 120.64(13) . . ?
C7 C9 C8 120.46(13) 7_556 . ?
C7 C9 C10 119.06(13) 7_556 . ?
C8 C9 C10 120.46(13) . . ?
N2 C10 C9 178.66(16) . . ?
N3 C11 C8 178.69(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -0.3(3) . . . . ?
C1 N1 C5 C4 1.3(2) . . . . ?
C1 C2 C3 C4 0.7(2) . . . . ?
C1 C2 C3 C6 179.76(16) . . . . ?
C1 C2 C3 C6A -176.4(5) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C2 C3 C6 C6 178.6(2) . . . 5_656 ?
C2 C3 C6A C6A -7.5(11) . . . 5_656 ?
C3 C4 C5 N1 -1.0(2) . . . . ?
C4 C3 C6 C6 -2.4(4) . . . 5_656 ?
C4 C3 C6A C6A 175.1(6) . . . 5_656 ?
C5 N1 C1 C2 -0.6(2) . . . . ?
C6 C3 C4 C5 -179.01(16) . . . . ?
C6A C3 C4 C5 178.5(3) . . . . ?
C7 C8 C9 C7 0.3(2) . . . 7_556 ?
C7 C8 C9 C10 179.01(13) . . . . ?
C9 C7 C8 C9 -0.3(2) 7_556 . . . ?
C9 C7 C8 C11 178.44(12) 7_556 . . . ?
C11 C8 C9 C7 -178.42(13) . . . 7_556 ?
C11 C8 C9 C10 0.3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.618
_oxdiff_exptl_absorpt_empirical_full_min 0.643
####################################################################### 
# 
# 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_CBZ-TCNB-hb
_audit_block_doi                 10.5517/ccdc.csd.cc241bfz
_database_code_depnum_ccdc_archive 'CCDC 1967490'
loop_
_audit_author_name
_audit_author_address
'Li Jie'
;State Key Laboratory of Chemical Engineering, Tianjin University
China
;
_audit_update_record             
;
2021-03-17 deposited with the CCDC.	2022-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H11 N5'
_chemical_formula_weight         345.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   24.906(5)
_cell_length_b                   7.2168(14)
_cell_length_c                   9.2906(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1669.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    3719
_cell_measurement_theta_min      2.4533
_cell_measurement_theta_max      27.9064

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.8725
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            14146
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.822
_diffrn_reflns_theta_max         27.891
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3467
_reflns_number_gt                3150
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.884
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0577P)²+0.4187P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3467
_refine_ls_number_parameters     247
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1196
_refine_ls_wR_factor_gt          0.1156
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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 0.44279(10) 0.6076(4) 1.0017(3) 0.0323(6) Uani 1 1 d D . . . .
H1 H 0.4763(7) 0.650(5) 1.022(4) 0.039 Uiso 1 1 d D U . . .
N2 N 0.45238(9) 0.2578(4) 0.6292(3) 0.0308(6) Uani 1 1 d . . . . .
N3 N 0.29605(10) 0.1545(4) 0.6005(3) 0.0298(6) Uani 1 1 d . . . . .
N4 N 0.29552(10) -0.1425(4) 1.3076(3) 0.0287(6) Uani 1 1 d . . . . .
N5 N 0.45305(10) -0.0331(4) 1.3313(3) 0.0309(6) Uani 1 1 d . . . . .
C1 C 0.41501(12) 0.6357(4) 0.8732(3) 0.0274(7) Uani 1 1 d . . . . .
C2 C 0.43385(13) 0.7091(5) 0.7428(4) 0.0356(8) Uani 1 1 d . . . . .
H2 H 0.470067 0.747676 0.731464 0.043 Uiso 1 1 calc R U . . .
C3 C 0.39696(14) 0.7226(4) 0.6311(4) 0.0377(8) Uani 1 1 d . . . . .
H3 H 0.408180 0.769802 0.540531 0.045 Uiso 1 1 calc R U . . .
C4 C 0.34355(15) 0.6678(4) 0.6500(4) 0.0353(8) Uani 1 1 d . . . . .
H4 H 0.319085 0.680162 0.572126 0.042 Uiso 1 1 calc R U . . .
C5 C 0.32562(13) 0.5965(4) 0.7783(4) 0.0306(7) Uani 1 1 d . . . . .
H5 H 0.289260 0.559257 0.789230 0.037 Uiso 1 1 calc R U . . .
C6 C 0.36146(12) 0.5798(4) 0.8913(3) 0.0248(6) Uani 1 1 d . . . . .
C7 C 0.35656(13) 0.5152(4) 1.0390(3) 0.0262(6) Uani 1 1 d . . . . .
C8 C 0.31454(13) 0.4402(4) 1.1205(4) 0.0299(7) Uani 1 1 d . . . . .
H8 H 0.279920 0.423859 1.079445 0.036 Uiso 1 1 calc R U . . .
C9 C 0.32429(15) 0.3905(4) 1.2609(4) 0.0354(8) Uani 1 1 d . . . . .
H9 H 0.296072 0.338851 1.316789 0.043 Uiso 1 1 calc R U . . .
C10 C 0.37472(15) 0.4146(5) 1.3228(4) 0.0396(8) Uani 1 1 d . . . . .
H10 H 0.379988 0.380226 1.420540 0.047 Uiso 1 1 calc R U . . .
C11 C 0.41712(15) 0.4868(5) 1.2462(4) 0.0358(8) Uani 1 1 d . . . . .
H11 H 0.451447 0.502299 1.289172 0.043 Uiso 1 1 calc R U . . .
C12 C 0.40790(12) 0.5364(4) 1.1033(4) 0.0284(7) Uani 1 1 d . . . . .
C13 C 0.42931(10) 0.2021(4) 0.7262(3) 0.0228(6) Uani 1 1 d . . . . .
C14 C 0.40102(10) 0.1286(4) 0.8491(3) 0.0195(6) Uani 1 1 d . . . . .
C15 C 0.42836(10) 0.1000(4) 0.9776(3) 0.0212(6) Uani 1 1 d . . . . .
H15 H 0.465416 0.129697 0.984904 0.025 Uiso 1 1 calc R U . . .
C16 C 0.40107(10) 0.0278(4) 1.0951(3) 0.0189(5) Uani 1 1 d . . . . .
C17 C 0.34615(10) -0.0170(4) 1.0841(3) 0.0190(6) Uani 1 1 d . . . . .
C18 C 0.31886(10) 0.0126(4) 0.9557(3) 0.0196(6) Uani 1 1 d . . . . .
H18 H 0.281808 -0.017194 0.948439 0.023 Uiso 1 1 calc R U . . .
C19 C 0.34584(10) 0.0858(4) 0.8384(3) 0.0191(5) Uani 1 1 d . . . . .
C20 C 0.31798(10) 0.1209(4) 0.7054(3) 0.0213(6) Uani 1 1 d . . . . .
C21 C 0.31794(10) -0.0883(4) 1.2081(3) 0.0212(6) Uani 1 1 d . . . . .
C22 C 0.42949(11) -0.0052(4) 1.2278(3) 0.0218(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C12 1.382(4) . ?
N1 C1 1.395(4) . ?
N1 H1 0.908(13) . ?
N2 C13 1.142(4) . ?
N3 C20 1.143(4) . ?
N4 C21 1.149(4) . ?
N5 C22 1.145(4) . ?
C1 C2 1.403(5) . ?
C1 C6 1.404(4) . ?
C2 C3 1.390(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.399(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.373(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.454(4) . ?
C7 C8 1.401(4) . ?
C7 C12 1.420(4) . ?
C8 C9 1.375(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.392(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.376(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.394(5) . ?
C11 H11 0.9500 . ?
C13 C14 1.443(4) . ?
C14 C15 1.390(4) . ?
C14 C19 1.412(4) . ?
C15 C16 1.388(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.409(4) . ?
C16 C22 1.441(4) . ?
C17 C18 1.389(4) . ?
C17 C21 1.444(4) . ?
C18 C19 1.385(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.440(4) . ?

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
C12 N1 C1 109.1(2) . . ?
C12 N1 H1 124(2) . . ?
C1 N1 H1 126(2) . . ?
N1 C1 C2 128.9(3) . . ?
N1 C1 C6 109.1(3) . . ?
C2 C1 C6 122.0(3) . . ?
C3 C2 C1 116.8(3) . . ?
C3 C2 H2 121.6 . . ?
C1 C2 H2 121.6 . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 121.6(3) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 118.8(3) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C1 119.8(3) . . ?
C5 C6 C7 133.6(3) . . ?
C1 C6 C7 106.5(3) . . ?
C8 C7 C12 119.1(3) . . ?
C8 C7 C6 134.2(3) . . ?
C12 C7 C6 106.7(3) . . ?
C9 C8 C7 118.8(3) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 121.3(3) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C11 C10 C9 121.7(3) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C12 117.6(3) . . ?
C10 C11 H11 121.2 . . ?
C12 C11 H11 121.2 . . ?
N1 C12 C11 130.0(3) . . ?
N1 C12 C7 108.6(3) . . ?
C11 C12 C7 121.4(3) . . ?
N2 C13 C14 178.8(3) . . ?
C15 C14 C19 120.3(2) . . ?
C15 C14 C13 119.7(2) . . ?
C19 C14 C13 120.0(3) . . ?
C16 C15 C14 119.5(2) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C17 120.3(2) . . ?
C15 C16 C22 119.6(2) . . ?
C17 C16 C22 120.0(2) . . ?
C18 C17 C16 120.1(2) . . ?
C18 C17 C21 120.1(2) . . ?
C16 C17 C21 119.8(2) . . ?
C19 C18 C17 119.8(2) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C14 120.0(3) . . ?
C18 C19 C20 120.6(2) . . ?
C14 C19 C20 119.4(2) . . ?
N3 C20 C19 177.9(3) . . ?
N4 C21 C17 179.0(3) . . ?
N5 C22 C16 178.4(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N1 C1 C2 178.5(3) . . . . ?
C12 N1 C1 C6 -0.7(3) . . . . ?
N1 C1 C2 C3 -179.6(3) . . . . ?
C6 C1 C2 C3 -0.5(5) . . . . ?
C1 C2 C3 C4 0.9(5) . . . . ?
C2 C3 C4 C5 -0.9(5) . . . . ?
C3 C4 C5 C6 0.3(5) . . . . ?
C4 C5 C6 C1 0.1(5) . . . . ?
C4 C5 C6 C7 178.8(3) . . . . ?
N1 C1 C6 C5 179.3(3) . . . . ?
C2 C1 C6 C5 0.0(5) . . . . ?
N1 C1 C6 C7 0.3(3) . . . . ?
C2 C1 C6 C7 -179.0(3) . . . . ?
C5 C6 C7 C8 2.6(6) . . . . ?
C1 C6 C7 C8 -178.6(3) . . . . ?
C5 C6 C7 C12 -178.6(3) . . . . ?
C1 C6 C7 C12 0.2(3) . . . . ?
C12 C7 C8 C9 0.5(4) . . . . ?
C6 C7 C8 C9 179.2(3) . . . . ?
C7 C8 C9 C10 0.4(5) . . . . ?
C8 C9 C10 C11 -0.8(5) . . . . ?
C9 C10 C11 C12 0.3(5) . . . . ?
C1 N1 C12 C11 -179.9(3) . . . . ?
C1 N1 C12 C7 0.9(3) . . . . ?
C10 C11 C12 N1 -178.6(3) . . . . ?
C10 C11 C12 C7 0.6(4) . . . . ?
C8 C7 C12 N1 178.4(3) . . . . ?
C6 C7 C12 N1 -0.7(3) . . . . ?
C8 C7 C12 C11 -1.0(4) . . . . ?
C6 C7 C12 C11 180.0(3) . . . . ?
C19 C14 C15 C16 0.5(4) . . . . ?
C13 C14 C15 C16 -179.4(3) . . . . ?
C14 C15 C16 C17 0.3(4) . . . . ?
C14 C15 C16 C22 178.9(3) . . . . ?
C15 C16 C17 C18 -0.6(4) . . . . ?
C22 C16 C17 C18 -179.2(3) . . . . ?
C15 C16 C17 C21 -178.6(3) . . . . ?
C22 C16 C17 C21 2.7(4) . . . . ?
C16 C17 C18 C19 0.2(4) . . . . ?
C21 C17 C18 C19 178.2(3) . . . . ?
C17 C18 C19 C14 0.5(4) . . . . ?
C17 C18 C19 C20 -178.8(3) . . . . ?
C15 C14 C19 C18 -0.9(4) . . . . ?
C13 C14 C19 C18 179.0(3) . . . . ?
C15 C14 C19 C20 178.4(3) . . . . ?
C13 C14 C19 C20 -1.7(4) . . . . ?

_refine_diff_density_max         0.291
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_DBF-TCNB-b
_audit_block_doi                 10.5517/ccdc.csd.cc241b9v
_database_code_depnum_ccdc_archive 'CCDC 1967486'
loop_
_audit_author_name
_audit_author_address
'Jie Li'
;State Key Laboratory of Chemical Engineering, Tianjin University
China
;
_audit_update_record             
;
2021-03-17 deposited with the CCDC.	2022-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H10 N4 O'
_chemical_formula_weight         346.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2494(14)
_cell_length_b                   7.8013(16)
_cell_length_c                   7.8557(16)
_cell_angle_alpha                73.68(3)
_cell_angle_beta                 81.08(3)
_cell_angle_gamma                84.74(3)
_cell_volume                     420.67(16)
_cell_formula_units_Z            1
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    1388
_cell_measurement_theta_min      2.7242
_cell_measurement_theta_max      27.8904

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             178
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.8977
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5038
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.848
_diffrn_reflns_theta_max         27.834
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             1994
_reflns_number_gt                1609
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0649P)²+0.0062P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1994
_refine_ls_number_parameters     181
_refine_ls_number_restraints     168
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.1131
_refine_ls_wR_factor_gt          0.1074
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.66158(13) 0.99960(12) -0.19606(12) 0.0310(2) Uani 1 1 d . . . . .
N2 N 0.36238(14) 0.30526(13) 0.52554(12) 0.0317(3) Uani 1 1 d . . . . .
C1 C 0.61816(14) 0.85447(13) -0.14029(12) 0.0219(2) Uani 1 1 d . . . . .
C2 C 0.55986(13) 0.67355(12) -0.06842(12) 0.0188(2) Uani 1 1 d . . . . .
C3 C 0.51492(13) 0.60513(13) 0.11575(13) 0.0203(2) Uani 1 1 d . . . . .
H3 H 0.525270 0.676046 0.193986 0.024 Uiso 1 1 calc R U . . .
C4 C 0.45470(13) 0.43192(13) 0.18408(12) 0.0186(2) Uani 1 1 d . . . . .
C5 C 0.40489(14) 0.36082(13) 0.37440(13) 0.0226(2) Uani 1 1 d . . . . .
O1 O -0.0206(2) 0.4149(2) 0.8230(2) 0.0311(4) Uani 0.5 1 d . U P A 1
C6 C 0.0396(4) 0.5826(4) 0.8013(6) 0.0255(6) Uani 0.5 1 d . U P A 1
C7 C 0.0960(8) 0.6995(7) 0.6372(9) 0.0336(10) Uani 0.5 1 d . U P A 1
H7A H 0.090319 0.692611 0.519265 0.040 Uiso 0.5 1 calc R U P A 1
C8 C 0.1522(6) 0.8647(8) 0.6453(5) 0.0370(10) Uani 0.5 1 d . U P A 1
H8A H 0.185175 0.960146 0.542046 0.044 Uiso 0.5 1 calc R U P A 1
C9 C 0.1524(5) 0.9064(5) 0.8076(6) 0.0341(8) Uani 0.5 1 d . U P A 1
H9A H 0.180080 1.024800 0.801675 0.041 Uiso 0.5 1 calc R U P A 1
C10 C 0.0977(7) 0.7818(7) 0.9700(6) 0.0282(9) Uani 0.5 1 d . U P A 1
H10A H 0.085695 0.825315 1.072826 0.034 Uiso 0.5 1 calc R U P A 1
C11 C 0.0391(7) 0.6181(7) 0.9645(7) 0.0199(9) Uani 0.5 1 d . U P A 1
C12 C -0.0248(3) 0.4605(4) 1.1000(4) 0.0218(5) Uani 0.5 1 d . U P A 1
C13 C -0.0561(4) 0.4082(5) 1.2872(5) 0.0283(6) Uani 0.5 1 d . U P A 1
H13A H -0.038683 0.504510 1.333980 0.034 Uiso 0.5 1 calc R U P A 1
C14 C -0.1194(8) 0.2396(7) 1.3697(9) 0.0318(11) Uani 0.5 1 d . U P A 1
H14A H -0.162958 0.214337 1.494181 0.038 Uiso 0.5 1 calc R U P A 1
C15 C -0.1541(5) 0.1232(5) 1.2736(8) 0.0380(10) Uani 0.5 1 d . U P A 1
H15 H -0.201040 0.003734 1.328826 0.046 Uiso 0.5 1 d R U P A 1
C16 C -0.1230(7) 0.1744(6) 1.0882(6) 0.0329(10) Uani 0.5 1 d . U P A 1
H16 H -0.144235 0.096381 1.019363 0.039 Uiso 0.5 1 d R U P A 1
C17 C -0.0587(8) 0.3425(7) 1.0068(8) 0.0213(8) Uani 0.5 1 d . U P A 1


_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 1.1474(13) . ?
N2 C5 1.1464(13) . ?
C1 C2 1.4411(14) . ?
C2 C3 1.3913(13) . ?
C2 C4 1.4070(14) 2_665 ?
C3 C4 1.3901(14) . ?
C3 H3 0.9500 . ?
C4 C5 1.4409(13) . ?
O1 C12 1.367(4) 2_567 ?
O1 C6 1.374(3) . ?
O1 C17 1.388(6) . ?
O1 C13 1.511(4) 2_567 ?
O1 C11 1.602(5) 2_567 ?
C6 C13 0.671(3) 2_567 ?
C6 C12 0.748(3) 2_567 ?
C6 C7 1.380(6) . ?
C6 C11 1.385(5) . ?
C6 C14 1.709(6) 2_567 ?
C6 C17 1.791(5) 2_567 ?
C7 C14 0.505(5) 2_567 ?
C7 C13 0.923(5) 2_567 ?
C7 C8 1.408(6) . ?
C7 C15 1.824(8) 2_567 ?
C7 H7A 0.9500 . ?
C8 C15 0.672(4) 2_567 ?
C8 C14 0.911(6) 2_567 ?
C8 C9 1.402(5) . ?
C8 C16 2.009(6) 2_567 ?
C8 H8A 0.9500 . ?
C9 C15 0.735(4) 2_567 ?
C9 C16 0.891(5) 2_567 ?
C9 C10 1.395(4) . ?
C9 H9A 0.9500 . ?
C10 C16 0.507(4) 2_567 ?
C10 C17 0.994(7) 2_567 ?
C10 C11 1.397(6) . ?
C10 C15 1.842(6) 2_567 ?
C10 H10A 0.9500 . ?
C11 C17 0.472(4) 2_567 ?
C11 C12 0.920(4) 2_567 ?
C11 C12 1.440(7) . ?
C11 C16 1.699(7) 2_567 ?
C11 C11 1.882(11) 2_567 ?
C11 C13 2.029(6) 2_567 ?
C12 C17 1.386(4) . ?
C12 C13 1.399(4) . ?
C12 C12 1.516(6) 2_567 ?
C12 C17 1.650(5) 2_567 ?
C13 C14 1.378(5) . ?
C13 H13A 0.9500 . ?
C14 C15 1.394(7) . ?
C14 H14A 0.9500 . ?
C15 C16 1.386(6) . ?
C15 H15 0.9786 . ?
C16 C17 1.376(6) . ?
C16 H16 0.9564 . ?

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
N1 C1 C2 178.76(11) . . ?
C3 C2 C4 120.29(9) . 2_665 ?
C3 C2 C1 119.55(9) . . ?
C4 C2 C1 120.16(9) 2_665 . ?
C4 C3 C2 119.31(9) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C2 120.40(9) . 2_665 ?
C3 C4 C5 119.75(9) . . ?
C2 C4 C5 119.85(9) 2_665 . ?
N2 C5 C4 178.91(11) . . ?
C12 O1 C6 31.67(15) 2_567 . ?
C12 O1 C17 73.55(19) 2_567 . ?
C6 O1 C17 105.2(2) . . ?
C12 O1 C13 57.90(17) 2_567 2_567 ?
C6 O1 C13 26.37(14) . 2_567 ?
C17 O1 C13 131.4(2) . 2_567 ?
C12 O1 C11 57.4(2) 2_567 2_567 ?
C6 O1 C11 89.0(2) . 2_567 ?
C17 O1 C11 16.2(2) . 2_567 ?
C13 O1 C11 115.3(2) 2_567 2_567 ?
C13 C6 C12 160.4(7) 2_567 2_567 ?
C13 C6 O1 88.3(5) 2_567 . ?
C12 C6 O1 73.7(4) 2_567 . ?
C13 C6 C7 35.8(4) 2_567 . ?
C12 C6 C7 161.7(5) 2_567 . ?
O1 C6 C7 124.0(4) . . ?
C13 C6 C11 159.9(6) 2_567 . ?
C12 C6 C11 38.1(3) 2_567 . ?
O1 C6 C11 111.5(4) . . ?
C7 C6 C11 124.5(4) . . ?
C13 C6 C14 50.1(5) 2_567 2_567 ?
C12 C6 C14 147.6(4) 2_567 2_567 ?
O1 C6 C14 138.3(3) . 2_567 ?
C7 C6 C14 14.3(4) . 2_567 ?
C11 C6 C14 110.1(4) . 2_567 ?
C13 C6 C17 151.1(5) 2_567 2_567 ?
C12 C6 C17 46.4(4) 2_567 2_567 ?
O1 C6 C17 120.1(3) . 2_567 ?
C7 C6 C17 115.9(4) . 2_567 ?
C11 C6 C17 8.8(4) . 2_567 ?
C14 C6 C17 101.5(3) 2_567 2_567 ?
C14 C7 C13 148.0(18) 2_567 2_567 ?
C14 C7 C6 123.1(17) 2_567 . ?
C13 C7 C6 25.2(3) 2_567 . ?
C14 C7 C8 8.4(12) 2_567 . ?
C13 C7 C8 139.8(7) 2_567 . ?
C6 C7 C8 114.8(6) . . ?
C14 C7 C15 27.3(13) 2_567 2_567 ?
C13 C7 C15 120.8(6) 2_567 2_567 ?
C6 C7 C15 95.8(4) . 2_567 ?
C8 C7 C15 19.0(2) . 2_567 ?
C14 C7 H7A 106.0 2_567 . ?
C13 C7 H7A 106.0 2_567 . ?
C6 C7 H7A 130.7 . . ?
C8 C7 H7A 114.1 . . ?
C15 C7 H7A 133.1 2_567 . ?
C15 C8 C14 122.7(8) 2_567 2_567 ?
C15 C8 C9 5.2(5) 2_567 . ?
C14 C8 C9 127.1(6) 2_567 . ?
C15 C8 C7 118.1(9) 2_567 . ?
C14 C8 C7 4.7(6) 2_567 . ?
C9 C8 C7 122.6(5) . . ?
C15 C8 C16 18.0(6) 2_567 2_567 ?
C14 C8 C16 104.8(5) 2_567 2_567 ?
C9 C8 C16 22.4(2) . 2_567 ?
C7 C8 C16 100.2(4) . 2_567 ?
C15 C8 H8A 118.7 2_567 . ?
C14 C8 H8A 118.7 2_567 . ?
C9 C8 H8A 114.1 . . ?
C7 C8 H8A 123.2 . . ?
C16 C8 H8A 136.5 2_567 . ?
C15 C9 C16 116.6(7) 2_567 2_567 ?
C15 C9 C10 116.3(7) 2_567 . ?
C16 C9 C10 2.6(5) 2_567 . ?
C15 C9 C8 4.7(4) 2_567 . ?
C16 C9 C8 120.8(6) 2_567 . ?
C10 C9 C8 120.3(5) . . ?
C15 C9 H9A 121.7 2_567 . ?
C16 C9 H9A 121.7 2_567 . ?
C10 C9 H9A 122.0 . . ?
C8 C9 H9A 117.5 . . ?
C16 C10 C17 130.1(15) 2_567 2_567 ?
C16 C10 C9 4.6(9) 2_567 . ?
C17 C10 C9 129.5(6) 2_567 . ?
C16 C10 C11 118.8(14) 2_567 . ?
C17 C10 C11 12.0(5) 2_567 . ?
C9 C10 C11 117.9(5) . . ?
C16 C10 C15 22.0(11) 2_567 2_567 ?
C17 C10 C15 108.6(5) 2_567 2_567 ?
C9 C10 C15 21.0(2) . 2_567 ?
C11 C10 C15 97.0(4) . 2_567 ?
C16 C10 H10A 115.0 2_567 . ?
C17 C10 H10A 115.0 2_567 . ?
C9 C10 H10A 115.2 . . ?
C11 C10 H10A 126.1 . . ?
C15 C10 H10A 136.1 2_567 . ?
C17 C11 C12 168.9(16) 2_567 2_567 ?
C17 C11 C6 144.7(16) 2_567 . ?
C12 C11 C6 30.1(2) 2_567 . ?
C17 C11 C10 26.0(12) 2_567 . ?
C12 C11 C10 149.6(6) 2_567 . ?
C6 C11 C10 119.9(5) . . ?
C17 C11 C12 108.2(14) 2_567 . ?
C12 C11 C12 76.4(5) 2_567 . ?
C6 C11 C12 106.4(4) . . ?
C10 C11 C12 133.7(4) . . ?
C17 C11 O1 55.3(13) 2_567 2_567 ?
C12 C11 O1 129.2(5) 2_567 2_567 ?
C6 C11 O1 159.3(5) . 2_567 ?
C10 C11 O1 80.6(3) . 2_567 ?
C12 C11 O1 53.1(2) . 2_567 ?
C17 C11 C16 40.6(13) 2_567 2_567 ?
C12 C11 C16 134.5(5) 2_567 2_567 ?
C6 C11 C16 104.8(4) . 2_567 ?
C10 C11 C16 15.1(3) . 2_567 ?
C12 C11 C16 148.7(4) . 2_567 ?
O1 C11 C16 95.6(3) 2_567 2_567 ?
C17 C11 C11 135.9(16) 2_567 2_567 ?
C12 C11 C11 48.1(3) 2_567 2_567 ?
C6 C11 C11 78.0(3) . 2_567 ?
C10 C11 C11 161.9(5) . 2_567 ?
C12 C11 C11 28.4(2) . 2_567 ?
O1 C11 C11 81.3(4) 2_567 2_567 ?
C16 C11 C11 175.4(5) 2_567 2_567 ?
C17 C11 C13 138.2(15) 2_567 2_567 ?
C12 C11 C13 36.4(3) 2_567 2_567 ?
C6 C11 C13 6.5(2) . 2_567 ?
C10 C11 C13 113.5(4) . 2_567 ?
C12 C11 C13 112.8(4) . 2_567 ?
O1 C11 C13 165.4(4) 2_567 2_567 ?
C16 C11 C13 98.4(3) 2_567 2_567 ?
C11 C11 C13 84.4(3) 2_567 2_567 ?
C6 C12 C11 111.8(5) 2_567 2_567 ?
C6 C12 O1 74.6(4) 2_567 2_567 ?
C11 C12 O1 171.1(4) 2_567 2_567 ?
C6 C12 C17 110.5(5) 2_567 . ?
C11 C12 C17 3.7(6) 2_567 . ?
O1 C12 C17 174.2(4) 2_567 . ?
C6 C12 C13 9.3(3) 2_567 . ?
C11 C12 C13 120.7(4) 2_567 . ?
O1 C12 C13 66.2(3) 2_567 . ?
C17 C12 C13 119.1(4) . . ?
C6 C12 C11 144.1(5) 2_567 . ?
C11 C12 C11 103.6(5) 2_567 . ?
O1 C12 C11 69.5(2) 2_567 . ?
C17 C12 C11 105.2(4) . . ?
C13 C12 C11 135.7(4) . . ?
C6 C12 C12 174.3(4) 2_567 2_567 ?
C11 C12 C12 67.4(5) 2_567 2_567 ?
O1 C12 C12 105.5(3) 2_567 2_567 ?
C17 C12 C12 69.1(3) . 2_567 ?
C13 C12 C12 171.5(4) . 2_567 ?
C11 C12 C12 36.1(2) . 2_567 ?
C6 C12 C17 128.3(5) 2_567 2_567 ?
C11 C12 C17 119.0(6) 2_567 2_567 ?
O1 C12 C17 53.8(3) 2_567 2_567 ?
C17 C12 C17 120.8(3) . 2_567 ?
C13 C12 C17 120.0(4) . 2_567 ?
C11 C12 C17 15.8(2) . 2_567 ?
C12 C12 C17 51.72(19) 2_567 2_567 ?
C6 C13 C7 119.0(7) 2_567 2_567 ?
C6 C13 C14 108.0(6) 2_567 . ?
C7 C13 C14 11.2(6) 2_567 . ?
C6 C13 C12 10.3(3) 2_567 . ?
C7 C13 C12 128.7(5) 2_567 . ?
C14 C13 C12 117.6(4) . . ?
C6 C13 O1 65.3(4) 2_567 2_567 ?
C7 C13 O1 174.5(5) 2_567 2_567 ?
C14 C13 O1 173.1(4) . 2_567 ?
C12 C13 O1 55.9(2) . 2_567 ?
C6 C13 C11 13.6(4) 2_567 2_567 ?
C7 C13 C11 105.8(5) 2_567 2_567 ?
C14 C13 C11 94.7(4) . 2_567 ?
C12 C13 C11 22.96(18) . 2_567 ?
O1 C13 C11 78.7(3) 2_567 2_567 ?
C6 C13 H13A 120.5 2_567 . ?
C7 C13 H13A 120.5 2_567 . ?
C14 C13 H13A 131.5 . . ?
C12 C13 H13A 110.7 . . ?
O1 C13 H13A 55.3 2_567 . ?
C11 C13 H13A 133.6 2_567 . ?
C7 C14 C8 166.9(18) 2_567 2_567 ?
C7 C14 C13 20.8(12) 2_567 . ?
C8 C14 C13 146.4(7) 2_567 . ?
C7 C14 C15 143.2(17) 2_567 . ?
C8 C14 C15 23.9(3) 2_567 . ?
C13 C14 C15 122.5(6) . . ?
C7 C14 C6 42.6(13) 2_567 2_567 ?
C8 C14 C6 124.5(6) 2_567 2_567 ?
C13 C14 C6 21.94(18) . 2_567 ?
C15 C14 C6 100.6(4) . 2_567 ?
C7 C14 H14A 96.6 2_567 . ?
C8 C14 H14A 96.6 2_567 . ?
C13 C14 H14A 116.6 . . ?
C15 C14 H14A 119.8 . . ?
C6 C14 H14A 138.3 2_567 . ?
C8 C15 C9 170.1(9) 2_567 2_567 ?
C8 C15 C16 153.4(8) 2_567 . ?
C9 C15 C16 35.1(4) 2_567 . ?
C8 C15 C14 33.4(6) 2_567 . ?
C9 C15 C14 154.9(7) 2_567 . ?
C16 C15 C14 120.1(5) . . ?
C8 C15 C7 42.9(7) 2_567 2_567 ?
C9 C15 C7 145.3(6) 2_567 2_567 ?
C16 C15 C7 110.6(3) . 2_567 ?
C14 C15 C7 9.6(4) . 2_567 ?
C8 C15 C10 145.5(8) 2_567 2_567 ?
C9 C15 C10 42.8(5) 2_567 2_567 ?
C16 C15 C10 7.9(4) . 2_567 ?
C14 C15 C10 112.3(4) . 2_567 ?
C7 C15 C10 102.8(3) 2_567 2_567 ?
C8 C15 H15 90.7 2_567 . ?
C9 C15 H15 80.9 2_567 . ?
C16 C15 H15 115.8 . . ?
C14 C15 H15 124.1 . . ?
C7 C15 H15 133.6 2_567 . ?
C10 C15 H15 123.6 2_567 . ?
C10 C16 C9 172.7(15) 2_567 2_567 ?
C10 C16 C17 33.6(11) 2_567 . ?
C9 C16 C17 145.2(6) 2_567 . ?
C10 C16 C15 150.1(15) 2_567 . ?
C9 C16 C15 28.3(3) 2_567 . ?
C17 C16 C15 117.1(5) . . ?
C10 C16 C11 46.1(12) 2_567 2_567 ?
C9 C16 C11 132.3(5) 2_567 2_567 ?
C17 C16 C11 12.9(3) . 2_567 ?
C15 C16 C11 104.3(4) . 2_567 ?
C10 C16 C8 141.5(14) 2_567 2_567 ?
C9 C16 C8 36.8(4) 2_567 2_567 ?
C17 C16 C8 108.5(4) . 2_567 ?
C15 C16 C8 8.6(3) . 2_567 ?
C11 C16 C8 95.7(3) 2_567 2_567 ?
C10 C16 H16 87.9 2_567 . ?
C9 C16 H16 93.4 2_567 . ?
C17 C16 H16 121.2 . . ?
C15 C16 H16 121.7 . . ?
C11 C16 H16 134.0 2_567 . ?
C8 C16 H16 130.3 2_567 . ?
C11 C17 C10 142.0(17) 2_567 2_567 ?
C11 C17 C16 126.5(16) 2_567 . ?
C10 C17 C16 16.4(4) 2_567 . ?
C11 C17 C12 7.3(11) 2_567 . ?
C10 C17 C12 139.8(7) 2_567 . ?
C16 C17 C12 123.6(5) . . ?
C11 C17 O1 108.5(15) 2_567 . ?
C10 C17 O1 108.4(5) 2_567 . ?
C16 C17 O1 124.6(4) . . ?
C12 C17 O1 111.8(4) . . ?
C11 C17 C12 56.1(13) 2_567 2_567 ?
C10 C17 C12 160.6(7) 2_567 2_567 ?
C16 C17 C12 176.7(5) . 2_567 ?
C12 C17 C12 59.2(3) . 2_567 ?
O1 C17 C12 52.6(2) . 2_567 ?
C11 C17 C6 26.5(13) 2_567 2_567 ?
C10 C17 C6 116.8(5) 2_567 2_567 ?
C16 C17 C6 100.6(4) . 2_567 ?
C12 C17 C6 23.03(18) . 2_567 ?
O1 C17 C6 134.7(4) . 2_567 ?
C12 C17 C6 82.1(3) 2_567 2_567 ?

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
C4 C2 C3 C4 -0.30(16) 2_665 . . . ?
C1 C2 C3 C4 178.55(8) . . . . ?
C2 C3 C4 C2 0.30(16) . . . 2_665 ?
C2 C3 C4 C5 -178.99(8) . . . . ?
C12 O1 C6 C13 172.1(5) 2_567 . . 2_567 ?
C17 O1 C6 C13 176.0(4) . . . 2_567 ?
C11 O1 C6 C13 174.1(4) 2_567 . . 2_567 ?
C17 O1 C6 C12 3.8(4) . . . 2_567 ?
C13 O1 C6 C12 -172.1(5) 2_567 . . 2_567 ?
C11 O1 C6 C12 2.0(3) 2_567 . . 2_567 ?
C12 O1 C6 C7 174.8(5) 2_567 . . . ?
C17 O1 C6 C7 178.7(4) . . . . ?
C13 O1 C6 C7 2.7(4) 2_567 . . . ?
C11 O1 C6 C7 176.8(4) 2_567 . . . ?
C12 O1 C6 C11 -4.3(3) 2_567 . . . ?
C17 O1 C6 C11 -0.4(2) . . . . ?
C13 O1 C6 C11 -176.4(5) 2_567 . . . ?
C11 O1 C6 C11 -2.3(5) 2_567 . . . ?
C12 O1 C6 C14 174.2(6) 2_567 . . 2_567 ?
C17 O1 C6 C14 178.1(4) . . . 2_567 ?
C13 O1 C6 C14 2.1(4) 2_567 . . 2_567 ?
C11 O1 C6 C14 176.2(4) 2_567 . . 2_567 ?
C12 O1 C6 C17 -2.3(3) 2_567 . . 2_567 ?
C17 O1 C6 C17 1.6(5) . . . 2_567 ?
C13 O1 C6 C17 -174.4(6) 2_567 . . 2_567 ?
C11 O1 C6 C17 -0.3(2) 2_567 . . 2_567 ?
C13 C6 C7 C14 -174(2) 2_567 . . 2_567 ?
C12 C6 C7 C14 -14(3) 2_567 . . 2_567 ?
O1 C6 C7 C14 -178.4(15) . . . 2_567 ?
C11 C6 C7 C14 0.5(18) . . . 2_567 ?
C17 C6 C7 C14 -1.3(18) 2_567 . . 2_567 ?
C12 C6 C7 C13 159.3(15) 2_567 . . 2_567 ?
O1 C6 C7 C13 -4.6(6) . . . 2_567 ?
C11 C6 C7 C13 174.4(7) . . . 2_567 ?
C14 C6 C7 C13 174(2) 2_567 . . 2_567 ?
C17 C6 C7 C13 172.6(7) 2_567 . . 2_567 ?
C13 C6 C7 C8 -175.4(9) 2_567 . . . ?
C12 C6 C7 C8 -16.1(16) 2_567 . . . ?
O1 C6 C7 C8 180.0(4) . . . . ?
C11 C6 C7 C8 -1.1(7) . . . . ?
C14 C6 C7 C8 -1.6(13) 2_567 . . . ?
C17 C6 C7 C8 -2.9(6) 2_567 . . . ?
C13 C6 C7 C15 -174.3(8) 2_567 . . 2_567 ?
C12 C6 C7 C15 -14.9(15) 2_567 . . 2_567 ?
O1 C6 C7 C15 -178.9(2) . . . 2_567 ?
C11 C6 C7 C15 0.1(5) . . . 2_567 ?
C14 C6 C7 C15 -0.4(15) 2_567 . . 2_567 ?
C17 C6 C7 C15 -1.7(4) 2_567 . . 2_567 ?
C14 C7 C8 C15 -167(7) 2_567 . . 2_567 ?
C13 C7 C8 C15 0.6(14) 2_567 . . 2_567 ?
C6 C7 C8 C15 3.6(10) . . . 2_567 ?
C13 C7 C8 C14 168(8) 2_567 . . 2_567 ?
C6 C7 C8 C14 171(7) . . . 2_567 ?
C15 C7 C8 C14 167(7) 2_567 . . 2_567 ?
C14 C7 C8 C9 -170(7) 2_567 . . . ?
C13 C7 C8 C9 -2.5(12) 2_567 . . . ?
C6 C7 C8 C9 0.5(8) . . . . ?
C15 C7 C8 C9 -3.1(5) 2_567 . . . ?
C14 C7 C8 C16 -169(7) 2_567 . . 2_567 ?
C13 C7 C8 C16 -1.0(10) 2_567 . . 2_567 ?
C6 C7 C8 C16 2.0(5) . . . 2_567 ?
C15 C7 C8 C16 -1.6(6) 2_567 . . 2_567 ?
C14 C8 C9 C15 31(5) 2_567 . . 2_567 ?
C7 C8 C9 C15 32(5) . . . 2_567 ?
C16 C8 C9 C15 28(5) 2_567 . . 2_567 ?
C15 C8 C9 C16 -28(5) 2_567 . . 2_567 ?
C14 C8 C9 C16 2.8(10) 2_567 . . 2_567 ?
C7 C8 C9 C16 3.8(9) . . . 2_567 ?
C15 C8 C9 C10 -31(5) 2_567 . . . ?
C14 C8 C9 C10 -0.2(9) 2_567 . . . ?
C7 C8 C9 C10 0.8(8) . . . . ?
C16 C8 C9 C10 -3.0(6) 2_567 . . . ?
C15 C9 C10 C16 97(12) 2_567 . . 2_567 ?
C8 C9 C10 C16 100(12) . . . 2_567 ?
C15 C9 C10 C17 -0.7(11) 2_567 . . 2_567 ?
C16 C9 C10 C17 -98(12) 2_567 . . 2_567 ?
C8 C9 C10 C17 2.0(10) . . . 2_567 ?
C15 C9 C10 C11 -4.3(8) 2_567 . . . ?
C16 C9 C10 C11 -102(12) 2_567 . . . ?
C8 C9 C10 C11 -1.6(7) . . . . ?
C16 C9 C10 C15 -97(12) 2_567 . . 2_567 ?
C8 C9 C10 C15 2.7(4) . . . 2_567 ?
C13 C6 C11 C17 -1(3) 2_567 . . 2_567 ?
C12 C6 C11 C17 162(3) 2_567 . . 2_567 ?
O1 C6 C11 C17 168(2) . . . 2_567 ?
C7 C6 C11 C17 -11(3) . . . 2_567 ?
C14 C6 C11 C17 -10(3) 2_567 . . 2_567 ?
C13 C6 C11 C12 -162.8(15) 2_567 . . 2_567 ?
O1 C6 C11 C12 6.7(4) . . . 2_567 ?
C7 C6 C11 C12 -172.4(6) . . . 2_567 ?
C14 C6 C11 C12 -172.3(5) 2_567 . . 2_567 ?
C17 C6 C11 C12 -162(3) 2_567 . . 2_567 ?
C13 C6 C11 C10 9.9(17) 2_567 . . . ?
C12 C6 C11 C10 172.7(7) 2_567 . . . ?
O1 C6 C11 C10 179.4(4) . . . . ?
C7 C6 C11 C10 0.3(7) . . . . ?
C14 C6 C11 C10 0.4(6) 2_567 . . . ?
C17 C6 C11 C10 11(2) 2_567 . . . ?
C13 C6 C11 C12 -169.0(14) 2_567 . . . ?
C12 C6 C11 C12 -6.2(4) 2_567 . . . ?
O1 C6 C11 C12 0.5(4) . . . . ?
C7 C6 C11 C12 -178.6(4) . . . . ?
C14 C6 C11 C12 -178.5(3) 2_567 . . . ?
C17 C6 C11 C12 -168(3) 2_567 . . . ?
C13 C6 C11 O1 -162.9(13) 2_567 . . 2_567 ?
C12 C6 C11 O1 -0.1(10) 2_567 . . 2_567 ?
O1 C6 C11 O1 6.6(13) . . . 2_567 ?
C7 C6 C11 O1 -172.5(10) . . . 2_567 ?
C14 C6 C11 O1 -172.4(11) 2_567 . . 2_567 ?
C17 C6 C11 O1 -162(4) 2_567 . . 2_567 ?
C13 C6 C11 C16 8.8(16) 2_567 . . 2_567 ?
C12 C6 C11 C16 171.6(6) 2_567 . . 2_567 ?
O1 C6 C11 C16 178.3(3) . . . 2_567 ?
C7 C6 C11 C16 -0.8(6) . . . 2_567 ?
C14 C6 C11 C16 -0.7(5) 2_567 . . 2_567 ?
C17 C6 C11 C16 10(2) 2_567 . . 2_567 ?
C13 C6 C11 C11 -167.5(14) 2_567 . . 2_567 ?
C12 C6 C11 C11 -4.6(3) 2_567 . . 2_567 ?
O1 C6 C11 C11 2.0(4) . . . 2_567 ?
C7 C6 C11 C11 -177.1(4) . . . 2_567 ?
C14 C6 C11 C11 -176.9(3) 2_567 . . 2_567 ?
C17 C6 C11 C11 -166(3) 2_567 . . 2_567 ?
C12 C6 C11 C13 162.8(15) 2_567 . . 2_567 ?
O1 C6 C11 C13 169.5(16) . . . 2_567 ?
C7 C6 C11 C13 -9.6(13) . . . 2_567 ?
C14 C6 C11 C13 -9.5(13) 2_567 . . 2_567 ?
C17 C6 C11 C13 1(3) 2_567 . . 2_567 ?
C16 C10 C11 C17 161(3) 2_567 . . 2_567 ?
C9 C10 C11 C17 167(3) . . . 2_567 ?
C15 C10 C11 C17 165(3) 2_567 . . 2_567 ?
C16 C10 C11 C12 3(2) 2_567 . . 2_567 ?
C17 C10 C11 C12 -158(3) 2_567 . . 2_567 ?
C9 C10 C11 C12 8.3(13) . . . 2_567 ?
C15 C10 C11 C12 6.7(12) 2_567 . . 2_567 ?
C16 C10 C11 C6 -4.1(16) 2_567 . . . ?
C17 C10 C11 C6 -166(3) 2_567 . . . ?
C9 C10 C11 C6 1.1(7) . . . . ?
C15 C10 C11 C6 -0.5(5) 2_567 . . . ?
C16 C10 C11 C12 174.5(13) 2_567 . . . ?
C17 C10 C11 C12 13(2) 2_567 . . . ?
C9 C10 C11 C12 179.6(5) . . . . ?
C15 C10 C11 C12 178.1(5) 2_567 . . . ?
C16 C10 C11 O1 173.3(14) 2_567 . . 2_567 ?
C17 C10 C11 O1 12(2) 2_567 . . 2_567 ?
C9 C10 C11 O1 178.5(5) . . . 2_567 ?
C15 C10 C11 O1 177.0(3) 2_567 . . 2_567 ?
C17 C10 C11 C16 -161(3) 2_567 . . 2_567 ?
C9 C10 C11 C16 5.2(11) . . . 2_567 ?
C15 C10 C11 C16 3.6(12) 2_567 . . 2_567 ?
C16 C10 C11 C11 167.6(19) 2_567 . . 2_567 ?
C17 C10 C11 C11 6.1(15) 2_567 . . 2_567 ?
C9 C10 C11 C11 172.8(16) . . . 2_567 ?
C15 C10 C11 C11 171.2(17) 2_567 . . 2_567 ?
C16 C10 C11 C13 -2.9(15) 2_567 . . 2_567 ?
C17 C10 C11 C13 -164(3) 2_567 . . 2_567 ?
C9 C10 C11 C13 2.3(6) . . . 2_567 ?
C15 C10 C11 C13 0.8(4) 2_567 . . 2_567 ?
C17 C11 C12 C6 0.8(18) 2_567 . . 2_567 ?
C12 C11 C12 C6 170.3(7) 2_567 . . 2_567 ?
C6 C11 C12 C6 173.5(5) . . . 2_567 ?
C10 C11 C12 C6 -5.2(11) . . . 2_567 ?
O1 C11 C12 C6 -3.8(6) 2_567 . . 2_567 ?
C16 C11 C12 C6 -2.4(13) 2_567 . . 2_567 ?
C11 C11 C12 C6 170.3(7) 2_567 . . 2_567 ?
C13 C11 C12 C6 172.1(5) 2_567 . . 2_567 ?
C17 C11 C12 C11 -169.5(17) 2_567 . . 2_567 ?
C12 C11 C12 C11 0.001(1) 2_567 . . 2_567 ?
C6 C11 C12 C11 3.2(2) . . . 2_567 ?
C10 C11 C12 C11 -175.5(8) . . . 2_567 ?
O1 C11 C12 C11 -174.1(4) 2_567 . . 2_567 ?
C16 C11 C12 C11 -172.7(11) 2_567 . . 2_567 ?
C13 C11 C12 C11 1.8(2) 2_567 . . 2_567 ?
C17 C11 C12 O1 4.6(14) 2_567 . . 2_567 ?
C12 C11 C12 O1 174.1(4) 2_567 . . 2_567 ?
C6 C11 C12 O1 177.3(4) . . . 2_567 ?
C10 C11 C12 O1 -1.4(5) . . . 2_567 ?
C16 C11 C12 O1 1.4(8) 2_567 . . 2_567 ?
C11 C11 C12 O1 174.1(4) 2_567 . . 2_567 ?
C13 C11 C12 O1 176.0(3) 2_567 . . 2_567 ?
C17 C11 C12 C17 -173.0(11) 2_567 . . . ?
C12 C11 C12 C17 -3.5(6) 2_567 . . . ?
C6 C11 C12 C17 -0.3(6) . . . . ?
C10 C11 C12 C17 -179.0(4) . . . . ?
O1 C11 C12 C17 -177.6(3) 2_567 . . . ?
C16 C11 C12 C17 -176.2(6) 2_567 . . . ?
C11 C11 C12 C17 -3.5(6) 2_567 . . . ?
C13 C11 C12 C17 -1.6(6) 2_567 . . . ?
C17 C11 C12 C13 6.9(17) 2_567 . . . ?
C12 C11 C12 C13 176.5(4) 2_567 . . . ?
C6 C11 C12 C13 179.7(3) . . . . ?
C10 C11 C12 C13 1.0(9) . . . . ?
O1 C11 C12 C13 2.4(4) 2_567 . . . ?
C16 C11 C12 C13 3.8(11) 2_567 . . . ?
C11 C11 C12 C13 176.5(4) 2_567 . . . ?
C13 C11 C12 C13 178.3(2) 2_567 . . . ?
C17 C11 C12 C12 -169.5(17) 2_567 . . 2_567 ?
C6 C11 C12 C12 3.2(2) . . . 2_567 ?
C10 C11 C12 C12 -175.5(8) . . . 2_567 ?
O1 C11 C12 C12 -174.1(4) 2_567 . . 2_567 ?
C16 C11 C12 C12 -172.7(11) 2_567 . . 2_567 ?
C11 C11 C12 C12 -0.001(3) 2_567 . . 2_567 ?
C13 C11 C12 C12 1.8(2) 2_567 . . 2_567 ?
C12 C11 C12 C17 169.5(17) 2_567 . . 2_567 ?
C6 C11 C12 C17 172.7(17) . . . 2_567 ?
C10 C11 C12 C17 -6.0(10) . . . 2_567 ?
O1 C11 C12 C17 -4.6(14) 2_567 . . 2_567 ?
C16 C11 C12 C17 -3.2(8) 2_567 . . 2_567 ?
C11 C11 C12 C17 169.5(17) 2_567 . . 2_567 ?
C13 C11 C12 C17 171.4(17) 2_567 . . 2_567 ?
C11 C12 C13 C6 19.1(17) 2_567 . . 2_567 ?
O1 C12 C13 C6 -154.5(17) 2_567 . . 2_567 ?
C17 C12 C13 C6 23.0(17) . . . 2_567 ?
C11 C12 C13 C6 -156.9(17) . . . 2_567 ?
C17 C12 C13 C6 -154.8(17) 2_567 . . 2_567 ?
C6 C12 C13 C7 -21.7(16) 2_567 . . 2_567 ?
C11 C12 C13 C7 -2.6(8) 2_567 . . 2_567 ?
O1 C12 C13 C7 -176.2(6) 2_567 . . 2_567 ?
C17 C12 C13 C7 1.3(7) . . . 2_567 ?
C11 C12 C13 C7 -178.6(6) . . . 2_567 ?
C17 C12 C13 C7 -176.5(5) 2_567 . . 2_567 ?
C6 C12 C13 C14 -22.9(16) 2_567 . . . ?
C11 C12 C13 C14 -3.8(6) 2_567 . . . ?
O1 C12 C13 C14 -177.4(4) 2_567 . . . ?
C17 C12 C13 C14 0.1(5) . . . . ?
C11 C12 C13 C14 -179.8(5) . . . . ?
C17 C12 C13 C14 -177.6(4) 2_567 . . . ?
C6 C12 C13 O1 154.5(17) 2_567 . . 2_567 ?
C11 C12 C13 O1 173.6(4) 2_567 . . 2_567 ?
C17 C12 C13 O1 177.5(4) . . . 2_567 ?
C11 C12 C13 O1 -2.4(4) . . . 2_567 ?
C17 C12 C13 O1 -0.2(3) 2_567 . . 2_567 ?
C6 C12 C13 C11 -19.1(17) 2_567 . . 2_567 ?
O1 C12 C13 C11 -173.6(4) 2_567 . . 2_567 ?
C17 C12 C13 C11 3.9(6) . . . 2_567 ?
C11 C12 C13 C11 -176.0(5) . . . 2_567 ?
C17 C12 C13 C11 -173.8(7) 2_567 . . 2_567 ?
C6 C13 C14 C7 171(3) 2_567 . . 2_567 ?
C12 C13 C14 C7 175(3) . . . 2_567 ?
C11 C13 C14 C7 174(3) 2_567 . . 2_567 ?
C6 C13 C14 C8 -3.0(13) 2_567 . . 2_567 ?
C7 C13 C14 C8 -174(4) 2_567 . . 2_567 ?
C12 C13 C14 C8 1.3(13) . . . 2_567 ?
C11 C13 C14 C8 -0.2(12) 2_567 . . 2_567 ?
C6 C13 C14 C15 -4.8(7) 2_567 . . . ?
C7 C13 C14 C15 -176(3) 2_567 . . . ?
C12 C13 C14 C15 -0.6(7) . . . . ?
C11 C13 C14 C15 -2.1(5) 2_567 . . . ?
C7 C13 C14 C6 -171(3) 2_567 . . 2_567 ?
C12 C13 C14 C6 4.2(3) . . . 2_567 ?
C11 C13 C14 C6 2.7(4) 2_567 . . 2_567 ?
C7 C14 C15 C8 175(3) 2_567 . . 2_567 ?
C13 C14 C15 C8 177.4(11) . . . 2_567 ?
C6 C14 C15 C8 175.6(10) 2_567 . . 2_567 ?
C7 C14 C15 C9 6(3) 2_567 . . 2_567 ?
C8 C14 C15 C9 -168.7(18) 2_567 . . 2_567 ?
C13 C14 C15 C9 8.8(16) . . . 2_567 ?
C6 C14 C15 C9 6.9(15) 2_567 . . 2_567 ?
C7 C14 C15 C16 -2(3) 2_567 . . . ?
C8 C14 C15 C16 -176.7(11) 2_567 . . . ?
C13 C14 C15 C16 0.7(7) . . . . ?
C6 C14 C15 C16 -1.1(5) 2_567 . . . ?
C8 C14 C15 C7 -175(3) 2_567 . . 2_567 ?
C13 C14 C15 C7 2(2) . . . 2_567 ?
C6 C14 C15 C7 1(2) 2_567 . . 2_567 ?
C7 C14 C15 C10 0(3) 2_567 . . 2_567 ?
C8 C14 C15 C10 -175.4(10) 2_567 . . 2_567 ?
C13 C14 C15 C10 2.0(7) . . . 2_567 ?
C6 C14 C15 C10 0.2(5) 2_567 . . 2_567 ?
C8 C15 C16 C10 5(3) 2_567 . . 2_567 ?
C9 C15 C16 C10 -165(3) 2_567 . . 2_567 ?
C14 C15 C16 C10 9(3) . . . 2_567 ?
C7 C15 C16 C10 8(3) 2_567 . . 2_567 ?
C8 C15 C16 C9 170.0(18) 2_567 . . 2_567 ?
C14 C15 C16 C9 174.1(8) . . . 2_567 ?
C7 C15 C16 C9 173.8(8) 2_567 . . 2_567 ?
C10 C15 C16 C9 165(3) 2_567 . . 2_567 ?
C8 C15 C16 C17 -4.4(18) 2_567 . . . ?
C9 C15 C16 C17 -174.4(8) 2_567 . . . ?
C14 C15 C16 C17 -0.3(7) . . . . ?
C7 C15 C16 C17 -0.6(6) 2_567 . . . ?
C10 C15 C16 C17 -9(2) 2_567 . . . ?
C8 C15 C16 C11 -2.5(17) 2_567 . . 2_567 ?
C9 C15 C16 C11 -172.5(8) 2_567 . . 2_567 ?
C14 C15 C16 C11 1.5(6) . . . 2_567 ?
C7 C15 C16 C11 1.2(5) 2_567 . . 2_567 ?
C10 C15 C16 C11 -7(2) 2_567 . . 2_567 ?
C9 C15 C16 C8 -170.0(18) 2_567 . . 2_567 ?
C14 C15 C16 C8 4.0(13) . . . 2_567 ?
C7 C15 C16 C8 3.7(14) 2_567 . . 2_567 ?
C10 C15 C16 C8 -5(3) 2_567 . . 2_567 ?
C10 C16 C17 C11 -164(3) 2_567 . . 2_567 ?
C9 C16 C17 C11 3(2) 2_567 . . 2_567 ?
C15 C16 C17 C11 8.1(19) . . . 2_567 ?
C8 C16 C17 C11 7.4(19) 2_567 . . 2_567 ?
C9 C16 C17 C10 167(3) 2_567 . . 2_567 ?
C15 C16 C17 C10 172(2) . . . 2_567 ?
C11 C16 C17 C10 164(3) 2_567 . . 2_567 ?
C8 C16 C17 C10 171(2) 2_567 . . 2_567 ?
C10 C16 C17 C12 -172.0(18) 2_567 . . . ?
C9 C16 C17 C12 -4.8(13) 2_567 . . . ?
C15 C16 C17 C12 -0.1(7) . . . . ?
C11 C16 C17 C12 -8.2(14) 2_567 . . . ?
C8 C16 C17 C12 -0.8(6) 2_567 . . . ?
C10 C16 C17 O1 8.1(19) 2_567 . . . ?
C9 C16 C17 O1 175.4(8) 2_567 . . . ?
C15 C16 C17 O1 -179.9(4) . . . . ?
C11 C16 C17 O1 172(2) 2_567 . . . ?
C8 C16 C17 O1 179.4(4) 2_567 . . . ?
C10 C16 C17 C6 -170.4(18) 2_567 . . 2_567 ?
C9 C16 C17 C6 -3.1(11) 2_567 . . 2_567 ?
C15 C16 C17 C6 1.5(5) . . . 2_567 ?
C11 C16 C17 C6 -6.6(16) 2_567 . . 2_567 ?
C8 C16 C17 C6 0.8(4) 2_567 . . 2_567 ?
C6 C12 C17 C11 -111(9) 2_567 . . 2_567 ?
C13 C12 C17 C11 -115(9) . . . 2_567 ?
C11 C12 C17 C11 65(9) . . . 2_567 ?
C12 C12 C17 C11 63(9) 2_567 . . 2_567 ?
C17 C12 C17 C11 63(9) 2_567 . . 2_567 ?
C6 C12 C17 C10 0.6(11) 2_567 . . 2_567 ?
C11 C12 C17 C10 112(9) 2_567 . . 2_567 ?
C13 C12 C17 C10 -3.3(11) . . . 2_567 ?
C11 C12 C17 C10 176.7(7) . . . 2_567 ?
C12 C12 C17 C10 174.5(10) 2_567 . . 2_567 ?
C17 C12 C17 C10 174.5(10) 2_567 . . 2_567 ?
C6 C12 C17 C16 4.1(7) 2_567 . . . ?
C11 C12 C17 C16 115(9) 2_567 . . . ?
C13 C12 C17 C16 0.2(7) . . . . ?
C11 C12 C17 C16 -179.8(3) . . . . ?
C12 C12 C17 C16 178.0(5) 2_567 . . . ?
C17 C12 C17 C16 178.0(5) 2_567 . . . ?
C6 C12 C17 O1 -176.1(4) 2_567 . . . ?
C11 C12 C17 O1 -65(9) 2_567 . . . ?
C13 C12 C17 O1 -179.9(3) . . . . ?
C11 C12 C17 O1 0.0(6) . . . . ?
C12 C12 C17 O1 -2.2(3) 2_567 . . . ?
C17 C12 C17 O1 -2.2(3) 2_567 . . . ?
C6 C12 C17 C12 -173.9(4) 2_567 . . 2_567 ?
C11 C12 C17 C12 -63(9) 2_567 . . 2_567 ?
C13 C12 C17 C12 -177.8(4) . . . 2_567 ?
C11 C12 C17 C12 2.2(4) . . . 2_567 ?
C17 C12 C17 C12 0.000(1) 2_567 . . 2_567 ?
C11 C12 C17 C6 111(9) 2_567 . . 2_567 ?
C13 C12 C17 C6 -3.9(3) . . . 2_567 ?
C11 C12 C17 C6 176.1(6) . . . 2_567 ?
C12 C12 C17 C6 173.9(4) 2_567 . . 2_567 ?
C17 C12 C17 C6 173.9(4) 2_567 . . 2_567 ?
C12 O1 C17 C11 -4.6(14) 2_567 . . 2_567 ?
C6 O1 C17 C11 -6.7(15) . . . 2_567 ?
C13 O1 C17 C11 -4.3(16) 2_567 . . 2_567 ?
C12 O1 C17 C10 -175.4(6) 2_567 . . 2_567 ?
C6 O1 C17 C10 -177.5(5) . . . 2_567 ?
C13 O1 C17 C10 -175.1(4) 2_567 . . 2_567 ?
C11 O1 C17 C10 -170.8(19) 2_567 . . 2_567 ?
C12 O1 C17 C16 -177.8(5) 2_567 . . . ?
C6 O1 C17 C16 -179.9(4) . . . . ?
C13 O1 C17 C16 -177.5(4) 2_567 . . . ?
C11 O1 C17 C16 -173.2(19) 2_567 . . . ?
C12 O1 C17 C12 2.3(4) 2_567 . . . ?
C6 O1 C17 C12 0.2(5) . . . . ?
C13 O1 C17 C12 2.6(6) 2_567 . . . ?
C11 O1 C17 C12 7.0(11) 2_567 . . . ?
C6 O1 C17 C12 -2.10(19) . . . 2_567 ?
C13 O1 C17 C12 0.3(3) 2_567 . . 2_567 ?
C11 O1 C17 C12 4.6(14) 2_567 . . 2_567 ?
C12 O1 C17 C6 0.2(5) 2_567 . . 2_567 ?
C6 O1 C17 C6 -1.9(6) . . . 2_567 ?
C13 O1 C17 C6 0.5(7) 2_567 . . 2_567 ?
C11 O1 C17 C6 4.8(10) 2_567 . . 2_567 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C16^a H16^a N1 0.96 2.66 3.531(6) 151.9 1_446 yes

_refine_diff_density_max         0.219
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_DBT-TCNB-b
_audit_block_doi                 10.5517/ccdc.csd.cc241bdy
_database_code_depnum_ccdc_archive 'CCDC 1967489'
loop_
_audit_author_name
_audit_author_address
'Li Jie '
;State Key Laboratory of Chemical Engineering, Tianjin University
China
;
_audit_update_record             
;
2021-03-17 deposited with the CCDC.	2022-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H5 N2 S0.50'
_chemical_formula_weight         181.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1834(14)
_cell_length_b                   7.8033(16)
_cell_length_c                   7.9522(16)
_cell_angle_alpha                73.00(3)
_cell_angle_beta                 85.67(3)
_cell_angle_gamma                88.65(3)
_cell_volume                     425.05(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    1161
_cell_measurement_theta_min      2.6854
_cell_measurement_theta_max      27.8625

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_F_000             186
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.205
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6194
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            3974
_diffrn_reflns_av_unetI/netI     0.0868
_diffrn_reflns_av_R_equivalents  0.0682
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.685
_diffrn_reflns_theta_max         25.019
_diffrn_reflns_theta_full        25.019
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1499
_reflns_number_gt                1118
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1598P)²+0.4410P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1499
_refine_ls_number_parameters     181
_refine_ls_number_restraints     23
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0803
_refine_ls_wR_factor_ref         0.2632
_refine_ls_wR_factor_gt          0.2522
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

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 0.6393(5) 0.6928(5) 0.4840(5) 0.0358(10) Uani 1 1 d . . . . .
N2 N 0.3389(5) -0.0106(5) 1.1969(5) 0.0364(10) Uani 1 1 d . . . . .
C1 C 0.5983(5) 0.6399(5) 0.6315(5) 0.0261(10) Uani 1 1 d . . . . .
C2 C 0.5472(5) 0.5681(5) 0.8190(5) 0.0223(9) Uani 1 1 d . . . . .
C3 C 0.4901(5) 0.3907(5) 0.8882(5) 0.0254(10) Uani 1 1 d . . . . .
H3A H 0.483488 0.316261 0.813258 0.030 Uiso 1 1 calc R U . . .
C4 C 0.4426(5) 0.3230(5) 1.0694(5) 0.0218(9) Uani 1 1 d . . . . .
C5 C 0.3844(5) 0.1377(5) 1.1414(5) 0.0257(10) Uani 1 1 d . . . . .
S1 S 0.0083(3) 0.6500(3) 1.1824(3) 0.0330(7) Uani 0.5 1 d D . P . .
C6 C -0.0535(14) 0.4361(12) 1.199(2) 0.027(4) Uani 0.5 1 d D . P A 1
C7 C -0.121(4) 0.302(3) 1.363(3) 0.031(4) Uani 0.5 1 d . U P A 1
H7A H -0.134025 0.328853 1.473968 0.037 Uiso 0.5 1 d R U P A 1
C8 C -0.178(4) 0.138(3) 1.349(3) 0.025(5) Uani 0.5 1 d . . P A 1
H8A H -0.227062 0.049032 1.453350 0.030 Uiso 0.5 1 d R U P A 1
C9 C -0.155(3) 0.104(3) 1.179(2) 0.023(3) Uani 0.5 1 d . . P A 1
H9A H -0.191287 -0.011651 1.172353 0.027 Uiso 0.5 1 d R U P A 1
C10 C -0.0881(18) 0.229(2) 1.0308(16) 0.029(3) Uani 0.5 1 d . . P A 1
H10A H -0.075523 0.202285 0.919922 0.035 Uiso 0.5 1 d R U P A 1
C11 C -0.0351(18) 0.397(2) 1.043(2) 0.023(3) Uani 0.5 1 d . . P A 1
C12 C 0.0317(16) 0.547(2) 0.892(2) 0.023(4) Uani 0.5 1 d . U P A 1
C13 C 0.0691(17) 0.5625(19) 0.717(2) 0.031(3) Uani 0.5 1 d D . P A 1
H13A H 0.053378 0.460800 0.674320 0.037 Uiso 0.5 1 d R U P A 1
C14 C 0.137(5) 0.723(3) 0.606(3) 0.048(8) Uani 0.5 1 d D U P A 1
H14A H 0.164067 0.733289 0.483860 0.058 Uiso 0.5 1 d R U P A 1
C15 C 0.154(4) 0.871(3) 0.667(4) 0.048(9) Uani 0.5 1 d D . P A 1
H15A H 0.183899 0.984432 0.582957 0.057 Uiso 0.5 1 d R U P A 1
C16 C 0.119(3) 0.852(3) 0.844(4) 0.065(10) Uani 0.5 1 d D . P A 1
H16A H 0.140969 0.952445 0.886788 0.078 Uiso 0.5 1 d R U P A 1
C17 C 0.0603(14) 0.687(3) 0.9553(19) 0.027(4) Uani 0.5 1 d D . P A 1


_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 1.142(5) . ?
N2 C5 1.157(5) . ?
C1 C2 1.453(5) . ?
C2 C3 1.390(5) . ?
C2 C4 1.403(5) 2_667 ?
C3 C4 1.401(5) . ?
C3 H3A 0.9500 . ?
C4 C5 1.450(5) . ?
S1 C13 1.703(14) 2_567 ?
S1 C6 1.702(8) . ?
S1 C10 1.743(13) 2_567 ?
S1 C17 1.755(15) . ?
S1 C12 1.835(17) 2_567 ?
S1 C11 1.92(2) 2_567 ?
S1 H10A 1.281(15) 2_567 ?
S1 H13A 1.268(15) 2_567 ?
C6 C13 0.676(12) 2_567 ?
C6 C12 0.699(13) 2_567 ?
C6 C11 1.36(2) . ?
C6 C7 1.47(2) . ?
C6 C14 1.75(2) 2_567 ?
C6 C17 1.770(18) 2_567 ?
C6 H13A 1.462(14) 2_567 ?
C7 C14 0.28(3) 2_567 ?
C7 C13 1.12(3) 2_567 ?
C7 C8 1.39(2) . ?
C7 C15 1.46(4) 2_567 ?
C7 H7A 0.9600 . ?
C8 C15 0.23(5) 2_567 ?
C8 C14 1.28(4) 2_567 ?
C8 C9 1.451(18) . ?
C8 C16 1.55(4) 2_567 ?
C8 H8A 0.9600 . ?
C8 H15A 0.95(4) 2_567 ?
C9 C16 0.43(3) 2_567 ?
C9 C15 1.30(4) 2_567 ?
C9 C10 1.36(2) . ?
C9 C17 1.79(3) 2_567 ?
C9 H9A 0.9600 . ?
C9 H16A 0.78(5) 2_567 ?
C10 C17 0.732(14) 2_567 ?
C10 C16 1.02(2) 2_567 ?
C10 C11 1.407(18) . ?
C10 H10A 0.9600 . ?
C10 H16A 1.420(15) 2_567 ?
C11 C17 0.680(13) 2_567 ?
C11 C12 0.775(15) 2_567 ?
C11 C12 1.470(16) . ?
C11 C11 1.63(3) 2_567 ?
C11 C16 1.975(19) 2_567 ?
C11 C13 2.03(2) 2_567 ?
C12 C17 1.358(19) . ?
C12 C13 1.367(16) . ?
C12 C12 1.70(3) 2_567 ?
C12 C17 1.97(2) 2_567 ?
C13 C14 1.380(10) . ?
C13 H13A 0.9600 . ?
C14 C15 1.379(10) . ?
C14 H14A 0.9600 . ?
C15 C16 1.380(10) . ?
C15 H15A 0.9601 . ?
C16 C17 1.385(10) . ?
C16 H16A 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 178.6(4) . . ?
C3 C2 C4 120.0(3) . 2_667 ?
C3 C2 C1 119.9(3) . . ?
C4 C2 C1 120.0(3) 2_667 . ?
C2 C3 C4 119.3(3) . . ?
C2 C3 H3A 120.4 . . ?
C4 C3 H3A 120.4 . . ?
C3 C4 C2 120.7(3) . 2_667 ?
C3 C4 C5 119.2(3) . . ?
C2 C4 C5 120.1(3) 2_667 . ?
N2 C5 C4 179.1(4) . . ?
C13 S1 C6 22.9(4) 2_567 . ?
C13 S1 C10 136.0(7) 2_567 2_567 ?
C6 S1 C10 113.1(7) . 2_567 ?
C13 S1 C17 111.9(7) 2_567 . ?
C6 S1 C17 89.0(7) . . ?
C10 S1 C17 24.2(4) 2_567 . ?
C13 S1 C12 45.3(5) 2_567 2_567 ?
C6 S1 C12 22.4(5) . 2_567 ?
C10 S1 C12 90.7(6) 2_567 2_567 ?
C17 S1 C12 66.6(6) . 2_567 ?
C13 S1 C11 91.2(6) 2_567 2_567 ?
C6 S1 C11 68.3(6) . 2_567 ?
C10 S1 C11 44.8(5) 2_567 2_567 ?
C17 S1 C11 20.6(5) . 2_567 ?
C12 S1 C11 46.0(4) 2_567 2_567 ?
C13 S1 H10A 168.5(8) 2_567 2_567 ?
C6 S1 H10A 145.7(8) . 2_567 ?
C10 S1 H10A 32.7(3) 2_567 2_567 ?
C17 S1 H10A 56.9(6) . 2_567 ?
C12 S1 H10A 123.4(7) 2_567 2_567 ?
C11 S1 H10A 77.5(6) 2_567 2_567 ?
C13 S1 H13A 33.8(4) 2_567 2_567 ?
C6 S1 H13A 56.7(6) . 2_567 ?
C10 S1 H13A 169.8(8) 2_567 2_567 ?
C17 S1 H13A 145.7(8) . 2_567 ?
C12 S1 H13A 79.1(7) 2_567 2_567 ?
C11 S1 H13A 125.0(7) 2_567 2_567 ?
H10A S1 H13A 157.5 2_567 2_567 ?
C13 C6 C12 168(2) 2_567 2_567 ?
C13 C6 C11 167.9(19) 2_567 . ?
C12 C6 C11 23.9(15) 2_567 . ?
C13 C6 C7 46.3(18) 2_567 . ?
C12 C6 C7 145.5(19) 2_567 . ?
C11 C6 C7 121.6(12) . . ?
C13 C6 S1 78.6(15) 2_567 . ?
C12 C6 S1 89.6(17) 2_567 . ?
C11 C6 S1 113.5(13) . . ?
C7 C6 S1 124.9(13) . . ?
C13 C6 C14 46.6(17) 2_567 2_567 ?
C12 C6 C14 145.2(18) 2_567 2_567 ?
C11 C6 C14 121.2(11) . 2_567 ?
C7 C6 C14 1(2) . 2_567 ?
S1 C6 C14 125.3(14) . 2_567 ?
C13 C6 C17 147.7(18) 2_567 2_567 ?
C12 C6 C17 44.1(15) 2_567 2_567 ?
C11 C6 C17 20.2(6) . 2_567 ?
C7 C6 C17 101.4(11) . 2_567 ?
S1 C6 C17 133.6(13) . 2_567 ?
C14 C6 C17 101.1(10) 2_567 2_567 ?
C13 C6 H13A 32.2(9) 2_567 2_567 ?
C12 C6 H13A 136.0(17) 2_567 2_567 ?
C11 C6 H13A 159.9(12) . 2_567 ?
C7 C6 H13A 78.5(12) . 2_567 ?
S1 C6 H13A 46.5(7) . 2_567 ?
C14 C6 H13A 78.8(12) 2_567 2_567 ?
C17 C6 H13A 178.4(10) 2_567 2_567 ?
C14 C7 C13 156(10) 2_567 2_567 ?
C14 C7 C8 61(9) 2_567 . ?
C13 C7 C8 143(2) 2_567 . ?
C14 C7 C15 67(9) 2_567 2_567 ?
C13 C7 C15 137(3) 2_567 2_567 ?
C8 C7 C15 9(2) . 2_567 ?
C14 C7 C6 176(10) 2_567 . ?
C13 C7 C6 26.0(8) 2_567 . ?
C8 C7 C6 116.9(18) . . ?
C15 C7 C6 111(2) 2_567 . ?
C14 C7 H7A 60.1 2_567 . ?
C13 C7 H7A 96.1 2_567 . ?
C8 C7 H7A 121.0 . . ?
C15 C7 H7A 126.8 2_567 . ?
C6 C7 H7A 122.0 . . ?
C15 C8 C14 111(10) 2_567 2_567 ?
C15 C8 C7 104(10) 2_567 . ?
C14 C8 C7 11.2(17) 2_567 . ?
C15 C8 C9 45(9) 2_567 . ?
C14 C8 C9 130(2) 2_567 . ?
C7 C8 C9 119(2) . . ?
C15 C8 C16 41(10) 2_567 2_567 ?
C14 C8 C16 114.6(17) 2_567 2_567 ?
C7 C8 C16 103.4(19) . 2_567 ?
C9 C8 C16 15.9(13) . 2_567 ?
C15 C8 H8A 116.7 2_567 . ?
C14 C8 H8A 107.9 2_567 . ?
C7 C8 H8A 119.0 . . ?
C9 C8 H8A 122.0 . . ?
C16 C8 H8A 137.1 2_567 . ?
C15 C8 H15A 86(10) 2_567 2_567 ?
C14 C8 H15A 130(3) 2_567 2_567 ?
C7 C8 H15A 139(3) . 2_567 ?
C9 C8 H15A 96(3) . 2_567 ?
C16 C8 H15A 109(3) 2_567 2_567 ?
H8A C8 H15A 31.8 . 2_567 ?
C16 C9 C15 92(6) 2_567 2_567 ?
C16 C9 C10 32(5) 2_567 . ?
C15 C9 C10 121(2) 2_567 . ?
C16 C9 C8 95(7) 2_567 . ?
C15 C9 C8 7(2) 2_567 . ?
C10 C9 C8 123(2) . . ?
C16 C9 C17 16(5) 2_567 2_567 ?
C15 C9 C17 99.6(16) 2_567 2_567 ?
C10 C9 C17 21.9(9) . 2_567 ?
C8 C9 C17 100.7(16) . 2_567 ?
C16 C9 H9A 143.9 2_567 . ?
C15 C9 H9A 118.7 2_567 . ?
C10 C9 H9A 119.4 . . ?
C8 C9 H9A 118.0 . . ?
C17 C9 H9A 141.3 2_567 . ?
C16 C9 H16A 102(7) 2_567 2_567 ?
C15 C9 H16A 154(3) 2_567 2_567 ?
C10 C9 H16A 78(2) . 2_567 ?
C8 C9 H16A 157(3) . 2_567 ?
C17 C9 H16A 100(2) 2_567 2_567 ?
H9A C9 H16A 42.2 . 2_567 ?
C17 C10 C16 103(2) 2_567 2_567 ?
C17 C10 C9 114.4(19) 2_567 . ?
C16 C10 C9 12.7(18) 2_567 . ?
C17 C10 C11 4.6(14) 2_567 . ?
C16 C10 C11 108(2) 2_567 . ?
C9 C10 C11 118.8(15) . . ?
C17 C10 S1 78.8(13) 2_567 2_567 ?
C16 C10 S1 172.5(18) 2_567 2_567 ?
C9 C10 S1 166.7(15) . 2_567 ?
C11 C10 S1 74.4(11) . 2_567 ?
C17 C10 H10A 125.0 2_567 . ?
C16 C10 H10A 131.0 2_567 . ?
C9 C10 H10A 120.6 . . ?
C11 C10 H10A 120.6 . . ?
S1 C10 H10A 46.2 2_567 . ?
C17 C10 H16A 146(2) 2_567 2_567 ?
C16 C10 H16A 42.5(6) 2_567 2_567 ?
C9 C10 H16A 32(2) . 2_567 ?
C11 C10 H16A 150.2(19) . 2_567 ?
S1 C10 H16A 134.5(17) 2_567 2_567 ?
H10A C10 H16A 88.6 . 2_567 ?
C17 C11 C12 138(3) 2_567 2_567 ?
C17 C11 C6 116(2) 2_567 . ?
C12 C11 C6 21.5(14) 2_567 . ?
C17 C11 C10 5.0(16) 2_567 . ?
C12 C11 C10 142(2) 2_567 . ?
C6 C11 C10 121.0(13) . . ?
C17 C11 C12 129(3) 2_567 . ?
C12 C11 C12 93(2) 2_567 . ?
C6 C11 C12 114(2) . . ?
C10 C11 C12 124(2) . . ?
C17 C11 C11 158(3) 2_567 2_567 ?
C12 C11 C11 64(2) 2_567 2_567 ?
C6 C11 C11 85.9(18) . 2_567 ?
C10 C11 C11 153(2) . 2_567 ?
C12 C11 C11 28.4(7) . 2_567 ?
C17 C11 S1 66(2) 2_567 2_567 ?
C12 C11 S1 157(2) 2_567 2_567 ?
C6 C11 S1 178.1(12) . 2_567 ?
C10 C11 S1 60.8(11) . 2_567 ?
C12 C11 S1 63.8(12) . 2_567 ?
C11 C11 S1 92.2(13) 2_567 2_567 ?
C17 C11 C16 25(2) 2_567 2_567 ?
C12 C11 C16 113(2) 2_567 2_567 ?
C6 C11 C16 91.9(11) . 2_567 ?
C10 C11 C16 29.4(11) . 2_567 ?
C12 C11 C16 154(2) . 2_567 ?
C11 C11 C16 178(2) 2_567 2_567 ?
S1 C11 C16 90.0(13) 2_567 2_567 ?
C17 C11 C13 112(2) 2_567 2_567 ?
C12 C11 C13 25.5(16) 2_567 2_567 ?
C6 C11 C13 4.0(6) . 2_567 ?
C10 C11 C13 117.0(11) . 2_567 ?
C12 C11 C13 118.4(18) . 2_567 ?
C11 C11 C13 90.0(17) 2_567 2_567 ?
S1 C11 C13 177.8(10) 2_567 2_567 ?
C16 C11 C13 87.8(10) 2_567 2_567 ?
C6 C12 C11 135(3) 2_567 2_567 ?
C6 C12 C17 114.9(19) 2_567 . ?
C11 C12 C17 19.7(15) 2_567 . ?
C6 C12 C13 5.8(10) 2_567 . ?
C11 C12 C13 140(2) 2_567 . ?
C17 C12 C13 120.7(15) . . ?
C6 C12 C11 138(3) 2_567 . ?
C11 C12 C11 87(2) 2_567 . ?
C17 C12 C11 107(2) . . ?
C13 C12 C11 132(2) . . ?
C6 C12 C12 165(3) 2_567 2_567 ?
C11 C12 C12 60.0(18) 2_567 2_567 ?
C17 C12 C12 79.6(15) . 2_567 ?
C13 C12 C12 160(2) . 2_567 ?
C11 C12 C12 27.1(9) . 2_567 ?
C6 C12 S1 68.1(14) 2_567 2_567 ?
C11 C12 S1 157(2) 2_567 2_567 ?
C17 C12 S1 176.9(14) . 2_567 ?
C13 C12 S1 62.3(10) . 2_567 ?
C11 C12 S1 70.2(12) . 2_567 ?
C12 C12 S1 97.4(12) 2_567 2_567 ?
C6 C12 C17 123(2) 2_567 2_567 ?
C11 C12 C17 103(2) 2_567 2_567 ?
C17 C12 C17 122.2(15) . 2_567 ?
C13 C12 C17 117.0(15) . 2_567 ?
C11 C12 C17 15.5(9) . 2_567 ?
C12 C12 C17 42.6(9) 2_567 2_567 ?
S1 C12 C17 54.8(7) 2_567 2_567 ?
C6 C13 C7 108(2) 2_567 2_567 ?
C6 C13 C12 6.0(11) 2_567 . ?
C7 C13 C12 113.7(19) 2_567 . ?
C6 C13 C14 113(2) 2_567 . ?
C7 C13 C14 5(2) 2_567 . ?
C12 C13 C14 118.5(18) . . ?
C6 C13 S1 78.5(14) 2_567 2_567 ?
C7 C13 S1 173.8(17) 2_567 2_567 ?
C12 C13 S1 72.5(11) . 2_567 ?
C14 C13 S1 169.0(17) . 2_567 ?
C6 C13 C11 8.1(13) 2_567 2_567 ?
C7 C13 C11 99.6(15) 2_567 2_567 ?
C12 C13 C11 14.1(9) . 2_567 ?
C14 C13 C11 104.4(14) . 2_567 ?
S1 C13 C11 86.6(9) 2_567 2_567 ?
C6 C13 H13A 125.8 2_567 . ?
C7 C13 H13A 126.4 2_567 . ?
C12 C13 H13A 119.8 . . ?
C14 C13 H13A 121.6 . . ?
S1 C13 H13A 47.4 2_567 . ?
C11 C13 H13A 133.9 2_567 . ?
C6 C13 H7A 146(2) 2_567 2_567 ?
C7 C13 H7A 38.1(8) 2_567 2_567 ?
C12 C13 H7A 151.8(18) . 2_567 ?
C14 C13 H7A 33.3(18) . 2_567 ?
S1 C13 H7A 135.7(13) 2_567 2_567 ?
C11 C13 H7A 137.7(13) 2_567 2_567 ?
H13A C13 H7A 88.4 . 2_567 ?
C7 C14 C8 108(10) 2_567 2_567 ?
C7 C14 C15 102(10) 2_567 . ?
C8 C14 C15 9(2) 2_567 . ?
C7 C14 C13 19(8) 2_567 . ?
C8 C14 C13 127(2) 2_567 . ?
C15 C14 C13 121(2) . . ?
C7 C14 C6 4(10) 2_567 2_567 ?
C8 C14 C6 106.1(19) 2_567 2_567 ?
C15 C14 C6 100.5(18) . 2_567 ?
C13 C14 C6 20.9(7) . 2_567 ?
C7 C14 H14A 137.3 2_567 . ?
C8 C14 H14A 114.8 2_567 . ?
C15 C14 H14A 120.3 . . ?
C13 C14 H14A 118.2 . . ?
C6 C14 H14A 139.1 2_567 . ?
C7 C14 H7A 103(9) 2_567 2_567 ?
C8 C14 H7A 149(3) 2_567 2_567 ?
C15 C14 H7A 154(3) . 2_567 ?
C13 C14 H7A 84(2) . 2_567 ?
C6 C14 H7A 105(2) 2_567 2_567 ?
H14A C14 H7A 34.1 . 2_567 ?
C8 C15 C9 128(10) 2_567 2_567 ?
C8 C15 C14 60(10) 2_567 . ?
C9 C15 C14 135(2) 2_567 . ?
C8 C15 C16 133(10) 2_567 . ?
C9 C15 C16 17.9(13) 2_567 . ?
C14 C15 C16 119(2) . . ?
C8 C15 C7 67(10) 2_567 2_567 ?
C9 C15 C7 125(2) 2_567 2_567 ?
C14 C15 C7 10.9(17) . 2_567 ?
C16 C15 C7 108(2) . 2_567 ?
C8 C15 H15A 80.7 2_567 . ?
C9 C15 H15A 105.7 2_567 . ?
C14 C15 H15A 118.7 . . ?
C16 C15 H15A 121.9 . . ?
C7 C15 H15A 129.4 2_567 . ?
C9 C16 C10 135(6) 2_567 2_567 ?
C9 C16 C15 70(5) 2_567 . ?
C10 C16 C15 149(2) 2_567 . ?
C9 C16 C17 159(6) 2_567 . ?
C10 C16 C17 31.0(8) 2_567 . ?
C15 C16 C17 119(2) . . ?
C9 C16 C8 69(6) 2_567 2_567 ?
C10 C16 C8 147(2) 2_567 2_567 ?
C15 C16 C8 6(2) . 2_567 ?
C17 C16 C8 117.1(19) . 2_567 ?
C9 C16 C11 160(7) 2_567 2_567 ?
C10 C16 C11 42.7(11) 2_567 2_567 ?
C15 C16 C11 106.9(17) . 2_567 ?
C17 C16 C11 11.8(10) . 2_567 ?
C8 C16 C11 105.5(14) 2_567 2_567 ?
C9 C16 H16A 52.1 2_567 . ?
C10 C16 H16A 91.7 2_567 . ?
C15 C16 H16A 118.8 . . ?
C17 C16 H16A 122.5 . . ?
C8 C16 H16A 119.7 2_567 . ?
C11 C16 H16A 134.3 2_567 . ?
C11 C17 C10 170(3) 2_567 2_567 ?
C11 C17 C12 22.6(19) 2_567 . ?
C10 C17 C12 166.2(19) 2_567 . ?
C11 C17 C16 144(3) 2_567 . ?
C10 C17 C16 45.7(18) 2_567 . ?
C12 C17 C16 121.2(16) . . ?
C11 C17 S1 94(2) 2_567 . ?
C10 C17 S1 77.0(15) 2_567 . ?
C12 C17 S1 116.4(14) . . ?
C16 C17 S1 122.3(18) . . ?
C11 C17 C6 43.5(19) 2_567 2_567 ?
C10 C17 C6 145.5(17) 2_567 2_567 ?
C12 C17 C6 21.0(6) . 2_567 ?
C16 C17 C6 100.2(15) . 2_567 ?
S1 C17 C6 137.4(13) . 2_567 ?
C11 C17 C9 145(2) 2_567 2_567 ?
C10 C17 C9 43.7(12) 2_567 2_567 ?
C12 C17 C9 122.9(12) . 2_567 ?
C16 C17 C9 5.0(14) . 2_567 ?
S1 C17 C9 120.7(12) . 2_567 ?
C6 C17 C9 101.9(10) 2_567 2_567 ?
C11 C17 C12 35(2) 2_567 2_567 ?
C10 C17 C12 135.5(18) 2_567 2_567 ?
C12 C17 C12 57.8(15) . 2_567 ?
C16 C17 C12 177.9(14) . 2_567 ?
S1 C17 C12 58.6(6) . 2_567 ?
C6 C17 C12 78.7(14) 2_567 2_567 ?
C9 C17 C12 177.0(9) 2_567 2_567 ?
C11 C17 H10A 139(2) 2_567 2_567 ?
C10 C17 H10A 31.5(9) 2_567 2_567 ?
C12 C17 H10A 161.8(13) . 2_567 ?
C16 C17 H10A 77.0(16) . 2_567 ?
S1 C17 H10A 45.5(7) . 2_567 ?
C6 C17 H10A 176.7(10) 2_567 2_567 ?
C9 C17 H10A 75.2(8) 2_567 2_567 ?
C12 C17 H10A 104.1(10) 2_567 2_567 ?

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
C4 C2 C3 C4 0.3(6) 2_667 . . . ?
C1 C2 C3 C4 179.5(3) . . . . ?
C2 C3 C4 C2 -0.3(6) . . . 2_667 ?
C2 C3 C4 C5 -179.6(3) . . . . ?
C10 S1 C6 C13 178.5(15) 2_567 . . 2_567 ?
C17 S1 C6 C13 -179.8(15) . . . 2_567 ?
C12 S1 C6 C13 180(2) 2_567 . . 2_567 ?
C11 S1 C6 C13 -179.4(16) 2_567 . . 2_567 ?
C13 S1 C6 C12 -180(2) 2_567 . . 2_567 ?
C10 S1 C6 C12 -1.4(13) 2_567 . . 2_567 ?
C17 S1 C6 C12 0.3(12) . . . 2_567 ?
C11 S1 C6 C12 0.7(11) 2_567 . . 2_567 ?
C13 S1 C6 C11 180(2) 2_567 . . . ?
C10 S1 C6 C11 -1.6(10) 2_567 . . . ?
C17 S1 C6 C11 0.1(9) . . . . ?
C12 S1 C6 C11 -0.2(10) 2_567 . . . ?
C11 S1 C6 C11 0.5(11) 2_567 . . . ?
C13 S1 C6 C7 0.1(17) 2_567 . . . ?
C10 S1 C6 C7 178.6(16) 2_567 . . . ?
C17 S1 C6 C7 -179.7(16) . . . . ?
C12 S1 C6 C7 180(2) 2_567 . . . ?
C11 S1 C6 C7 -179.3(17) 2_567 . . . ?
C13 S1 C6 C14 0.9(19) 2_567 . . 2_567 ?
C10 S1 C6 C14 179.3(16) 2_567 . . 2_567 ?
C17 S1 C6 C14 -178.9(17) . . . 2_567 ?
C12 S1 C6 C14 -179(2) 2_567 . . 2_567 ?
C11 S1 C6 C14 -178.6(17) 2_567 . . 2_567 ?
C13 S1 C6 C17 179(2) 2_567 . . 2_567 ?
C10 S1 C6 C17 -2.1(12) 2_567 . . 2_567 ?
C17 S1 C6 C17 -0.4(12) . . . 2_567 ?
C12 S1 C6 C17 -0.7(10) 2_567 . . 2_567 ?
C11 S1 C6 C17 0.0(9) 2_567 . . 2_567 ?
C12 C6 C7 C13 180(4) 2_567 . . 2_567 ?
C11 C6 C7 C13 -180(2) . . . 2_567 ?
S1 C6 C7 C13 0(2) . . . 2_567 ?
C14 C6 C7 C13 -117(100) 2_567 . . 2_567 ?
C17 C6 C7 C13 -180(2) 2_567 . . 2_567 ?
C13 C6 C7 C8 176(4) 2_567 . . . ?
C12 C6 C7 C8 -5(5) 2_567 . . . ?
C11 C6 C7 C8 -4(3) . . . . ?
S1 C6 C7 C8 175.4(17) . . . . ?
C14 C6 C7 C8 58(100) 2_567 . . . ?
C17 C6 C7 C8 -4(3) 2_567 . . . ?
C13 C6 C7 C15 -177(3) 2_567 . . 2_567 ?
C12 C6 C7 C15 3(4) 2_567 . . 2_567 ?
C11 C6 C7 C15 3(3) . . . 2_567 ?
S1 C6 C7 C15 -177.4(16) . . . 2_567 ?
C14 C6 C7 C15 65(100) 2_567 . . 2_567 ?
C17 C6 C7 C15 3(2) 2_567 . . 2_567 ?
C14 C7 C8 C15 -134(18) 2_567 . . 2_567 ?
C13 C7 C8 C15 53(13) 2_567 . . 2_567 ?
C6 C7 C8 C15 50(11) . . . 2_567 ?
C13 C7 C8 C14 -173(19) 2_567 . . 2_567 ?
C15 C7 C8 C14 134(18) 2_567 . . 2_567 ?
C6 C7 C8 C14 -176(17) . . . 2_567 ?
C14 C7 C8 C9 -180(14) 2_567 . . . ?
C13 C7 C8 C9 8(6) 2_567 . . . ?
C15 C7 C8 C9 -46(10) 2_567 . . . ?
C6 C7 C8 C9 4(3) . . . . ?
C14 C7 C8 C16 -176(15) 2_567 . . 2_567 ?
C13 C7 C8 C16 11(5) 2_567 . . 2_567 ?
C15 C7 C8 C16 -42(10) 2_567 . . 2_567 ?
C6 C7 C8 C16 8(3) . . . 2_567 ?
C15 C8 C9 C16 -67(16) 2_567 . . 2_567 ?
C14 C8 C9 C16 13(7) 2_567 . . 2_567 ?
C7 C8 C9 C16 14(6) . . . 2_567 ?
C14 C8 C9 C15 80(15) 2_567 . . 2_567 ?
C7 C8 C9 C15 80(15) . . . 2_567 ?
C16 C8 C9 C15 67(16) 2_567 . . 2_567 ?
C15 C8 C9 C10 -83(15) 2_567 . . . ?
C14 C8 C9 C10 -3(4) 2_567 . . . ?
C7 C8 C9 C10 -3(3) . . . . ?
C16 C8 C9 C10 -17(5) 2_567 . . . ?
C15 C8 C9 C17 -82(15) 2_567 . . 2_567 ?
C14 C8 C9 C17 -2(4) 2_567 . . 2_567 ?
C7 C8 C9 C17 -2(2) . . . 2_567 ?
C16 C8 C9 C17 -16(5) 2_567 . . 2_567 ?
C16 C9 C10 C17 -30(11) 2_567 . . 2_567 ?
C15 C9 C10 C17 -5(3) 2_567 . . 2_567 ?
C8 C9 C10 C17 3(3) . . . 2_567 ?
C15 C9 C10 C16 25(9) 2_567 . . 2_567 ?
C8 C9 C10 C16 33(10) . . . 2_567 ?
C17 C9 C10 C16 30(11) 2_567 . . 2_567 ?
C16 C9 C10 C11 -31(11) 2_567 . . . ?
C15 C9 C10 C11 -7(3) 2_567 . . . ?
C8 C9 C10 C11 1(3) . . . . ?
C17 C9 C10 C11 -1.6(12) 2_567 . . . ?
C16 C9 C10 S1 146(9) 2_567 . . 2_567 ?
C15 C9 C10 S1 171(5) 2_567 . . 2_567 ?
C8 C9 C10 S1 179(5) . . . 2_567 ?
C17 C9 C10 S1 176(7) 2_567 . . 2_567 ?
C13 C6 C11 C17 1(10) 2_567 . . 2_567 ?
C12 C6 C11 C17 -179(4) 2_567 . . 2_567 ?
C7 C6 C11 C17 1(3) . . . 2_567 ?
S1 C6 C11 C17 -178.9(18) . . . 2_567 ?
C14 C6 C11 C17 0(3) 2_567 . . 2_567 ?
C13 C6 C11 C12 -180(100) 2_567 . . 2_567 ?
C7 C6 C11 C12 -180(3) . . . 2_567 ?
S1 C6 C11 C12 0(2) . . . 2_567 ?
C14 C6 C11 C12 180(3) 2_567 . . 2_567 ?
C17 C6 C11 C12 179(4) 2_567 . . 2_567 ?
C13 C6 C11 C10 3(10) 2_567 . . . ?
C12 C6 C11 C10 -178(3) 2_567 . . . ?
C7 C6 C11 C10 3(2) . . . . ?
S1 C6 C11 C10 -177.1(12) . . . . ?
C14 C6 C11 C10 2(2) 2_567 . . . ?
C17 C6 C11 C10 1.8(13) 2_567 . . . ?
C13 C6 C11 C12 179(9) 2_567 . . . ?
C12 C6 C11 C12 -1(3) 2_567 . . . ?
C7 C6 C11 C12 179.1(16) . . . . ?
S1 C6 C11 C12 -0.8(13) . . . . ?
C14 C6 C11 C12 178.3(16) 2_567 . . . ?
C17 C6 C11 C12 178(3) 2_567 . . . ?
C13 C6 C11 C11 179(100) 2_567 . . 2_567 ?
C12 C6 C11 C11 -1(2) 2_567 . . 2_567 ?
C7 C6 C11 C11 179.3(17) . . . 2_567 ?
S1 C6 C11 C11 -0.6(12) . . . 2_567 ?
C14 C6 C11 C11 178.5(17) 2_567 . . 2_567 ?
C17 C6 C11 C11 178(3) 2_567 . . 2_567 ?
C13 C6 C11 C16 -1(9) 2_567 . . 2_567 ?
C12 C6 C11 C16 178(3) 2_567 . . 2_567 ?
C7 C6 C11 C16 -1.2(18) . . . 2_567 ?
S1 C6 C11 C16 178.9(9) . . . 2_567 ?
C14 C6 C11 C16 -2.0(18) 2_567 . . 2_567 ?
C17 C6 C11 C16 -2.2(18) 2_567 . . 2_567 ?
C12 C6 C11 C13 180(100) 2_567 . . 2_567 ?
C7 C6 C11 C13 0(8) . . . 2_567 ?
S1 C6 C11 C13 -180(100) . . . 2_567 ?
C14 C6 C11 C13 -1(9) 2_567 . . 2_567 ?
C17 C6 C11 C13 -1(10) 2_567 . . 2_567 ?
C16 C10 C11 C17 11(14) 2_567 . . 2_567 ?
C9 C10 C11 C17 18(13) . . . 2_567 ?
S1 C10 C11 C17 -162(14) 2_567 . . 2_567 ?
C17 C10 C11 C12 -20(13) 2_567 . . 2_567 ?
C16 C10 C11 C12 -10(4) 2_567 . . 2_567 ?
C9 C10 C11 C12 -3(4) . . . 2_567 ?
S1 C10 C11 C12 178(3) 2_567 . . 2_567 ?
C17 C10 C11 C6 -19(13) 2_567 . . . ?
C16 C10 C11 C6 -8(2) 2_567 . . . ?
C9 C10 C11 C6 -1(2) . . . . ?
S1 C10 C11 C6 179.3(12) 2_567 . . . ?
C17 C10 C11 C12 165(14) 2_567 . . . ?
C16 C10 C11 C12 176.0(16) 2_567 . . . ?
C9 C10 C11 C12 -177.1(13) . . . . ?
S1 C10 C11 C12 3.4(14) 2_567 . . . ?
C17 C10 C11 C11 169(15) 2_567 . . 2_567 ?
C16 C10 C11 C11 179(3) 2_567 . . 2_567 ?
C9 C10 C11 C11 -174(3) . . . 2_567 ?
S1 C10 C11 C11 7(4) 2_567 . . 2_567 ?
C17 C10 C11 S1 162(14) 2_567 . . 2_567 ?
C16 C10 C11 S1 172.6(18) 2_567 . . 2_567 ?
C9 C10 C11 S1 179.5(16) . . . 2_567 ?
C17 C10 C11 C16 -11(14) 2_567 . . 2_567 ?
C9 C10 C11 C16 7(2) . . . 2_567 ?
S1 C10 C11 C16 -172.6(18) 2_567 . . 2_567 ?
C17 C10 C11 C13 -19(13) 2_567 . . 2_567 ?
C16 C10 C11 C13 -8(2) 2_567 . . 2_567 ?
C9 C10 C11 C13 -1(2) . . . 2_567 ?
S1 C10 C11 C13 179.5(9) 2_567 . . 2_567 ?
C17 C11 C12 C6 -3(4) 2_567 . . 2_567 ?
C12 C11 C12 C6 179(3) 2_567 . . 2_567 ?
C6 C11 C12 C6 179.2(17) . . . 2_567 ?
C10 C11 C12 C6 -5(3) . . . 2_567 ?
C11 C11 C12 C6 179(3) 2_567 . . 2_567 ?
S1 C11 C12 C6 -1(2) 2_567 . . 2_567 ?
C16 C11 C12 C6 0(4) 2_567 . . 2_567 ?
C13 C11 C12 C6 179.3(19) 2_567 . . 2_567 ?
C17 C11 C12 C11 178(3) 2_567 . . 2_567 ?
C12 C11 C12 C11 -0.001(2) 2_567 . . 2_567 ?
C6 C11 C12 C11 0.5(10) . . . 2_567 ?
C10 C11 C12 C11 177(2) . . . 2_567 ?
S1 C11 C12 C11 179.9(14) 2_567 . . 2_567 ?
C16 C11 C12 C11 -179(3) 2_567 . . 2_567 ?
C13 C11 C12 C11 0.5(12) 2_567 . . 2_567 ?
C17 C11 C12 C17 179.0(19) 2_567 . . . ?
C12 C11 C12 C17 0.7(13) 2_567 . . . ?
C6 C11 C12 C17 1.1(15) . . . . ?
C10 C11 C12 C17 177.3(13) . . . . ?
C11 C11 C12 C17 0.7(13) 2_567 . . . ?
S1 C11 C12 C17 -179.4(9) 2_567 . . . ?
C16 C11 C12 C17 -178(2) 2_567 . . . ?
C13 C11 C12 C17 1.2(15) 2_567 . . . ?
C17 C11 C12 C13 -3(3) 2_567 . . . ?
C12 C11 C12 C13 179(2) 2_567 . . . ?
C6 C11 C12 C13 179.5(14) . . . . ?
C10 C11 C12 C13 -4(2) . . . . ?
C11 C11 C12 C13 179(2) 2_567 . . . ?
S1 C11 C12 C13 -1.0(14) 2_567 . . . ?
C16 C11 C12 C13 0(4) 2_567 . . . ?
C13 C11 C12 C13 179.6(9) 2_567 . . . ?
C17 C11 C12 C12 178(3) 2_567 . . 2_567 ?
C6 C11 C12 C12 0.5(10) . . . 2_567 ?
C10 C11 C12 C12 177(2) . . . 2_567 ?
C11 C11 C12 C12 0.001(10) 2_567 . . 2_567 ?
S1 C11 C12 C12 179.9(14) 2_567 . . 2_567 ?
C16 C11 C12 C12 -179(3) 2_567 . . 2_567 ?
C13 C11 C12 C12 0.5(12) 2_567 . . 2_567 ?
C17 C11 C12 S1 -2(2) 2_567 . . 2_567 ?
C12 C11 C12 S1 -179.9(14) 2_567 . . 2_567 ?
C6 C11 C12 S1 -179.5(11) . . . 2_567 ?
C10 C11 C12 S1 -3.3(13) . . . 2_567 ?
C11 C11 C12 S1 -179.9(14) 2_567 . . 2_567 ?
C16 C11 C12 S1 1(3) 2_567 . . 2_567 ?
C13 C11 C12 S1 -179.4(9) 2_567 . . 2_567 ?
C12 C11 C12 C17 -178(3) 2_567 . . 2_567 ?
C6 C11 C12 C17 -178(3) . . . 2_567 ?
C10 C11 C12 C17 -1.7(15) . . . 2_567 ?
C11 C11 C12 C17 -178(3) 2_567 . . 2_567 ?
S1 C11 C12 C17 2(2) 2_567 . . 2_567 ?
C16 C11 C12 C17 3(2) 2_567 . . 2_567 ?
C13 C11 C12 C17 -178(3) 2_567 . . 2_567 ?
C11 C12 C13 C6 0(11) 2_567 . . 2_567 ?
C17 C12 C13 C6 0(11) . . . 2_567 ?
C11 C12 C13 C6 -178(10) . . . 2_567 ?
C12 C12 C13 C6 -177(11) 2_567 . . 2_567 ?
S1 C12 C13 C6 -179(100) 2_567 . . 2_567 ?
C17 C12 C13 C6 -179(100) 2_567 . . 2_567 ?
C6 C12 C13 C7 0(10) 2_567 . . 2_567 ?
C11 C12 C13 C7 0(4) 2_567 . . 2_567 ?
C17 C12 C13 C7 -1(2) . . . 2_567 ?
C11 C12 C13 C7 -178.8(19) . . . 2_567 ?
C12 C12 C13 C7 -178(4) 2_567 . . 2_567 ?
S1 C12 C13 C7 -180(2) 2_567 . . 2_567 ?
C17 C12 C13 C7 -179.6(18) 2_567 . . 2_567 ?
C6 C12 C13 C14 0(10) 2_567 . . . ?
C11 C12 C13 C14 1(4) 2_567 . . . ?
C17 C12 C13 C14 0(3) . . . . ?
C11 C12 C13 C14 -178(2) . . . . ?
C12 C12 C13 C14 -177(4) 2_567 . . . ?
S1 C12 C13 C14 -179(2) 2_567 . . . ?
C17 C12 C13 C14 -178.7(19) 2_567 . . . ?
C6 C12 C13 S1 179(100) 2_567 . . 2_567 ?
C11 C12 C13 S1 180(2) 2_567 . . 2_567 ?
C17 C12 C13 S1 179.2(11) . . . 2_567 ?
C11 C12 C13 S1 1.1(15) . . . 2_567 ?
C12 C12 C13 S1 2(4) 2_567 . . 2_567 ?
C17 C12 C13 S1 0.3(9) 2_567 . . 2_567 ?
C6 C12 C13 C11 0(11) 2_567 . . 2_567 ?
C17 C12 C13 C11 -0.3(19) . . . 2_567 ?
C11 C12 C13 C11 -178(3) . . . 2_567 ?
C12 C12 C13 C11 -177(6) 2_567 . . 2_567 ?
S1 C12 C13 C11 -180(2) 2_567 . . 2_567 ?
C17 C12 C13 C11 -179(3) 2_567 . . 2_567 ?
C6 C13 C14 C7 -10(37) 2_567 . . 2_567 ?
C12 C13 C14 C7 -10(37) . . . 2_567 ?
S1 C13 C14 C7 175(28) 2_567 . . 2_567 ?
C11 C13 C14 C7 -10(36) 2_567 . . 2_567 ?
C6 C13 C14 C8 3(5) 2_567 . . 2_567 ?
C7 C13 C14 C8 13(33) 2_567 . . 2_567 ?
C12 C13 C14 C8 3(5) . . . 2_567 ?
S1 C13 C14 C8 -172(7) 2_567 . . 2_567 ?
C11 C13 C14 C8 3(4) 2_567 . . 2_567 ?
C6 C13 C14 C15 -5(4) 2_567 . . . ?
C7 C13 C14 C15 5(33) 2_567 . . . ?
C12 C13 C14 C15 -5(4) . . . . ?
S1 C13 C14 C15 -180(7) 2_567 . . . ?
C11 C13 C14 C15 -5(4) 2_567 . . . ?
C7 C13 C14 C6 10(37) 2_567 . . 2_567 ?
C12 C13 C14 C6 0.0(12) . . . 2_567 ?
S1 C13 C14 C6 -175(11) 2_567 . . 2_567 ?
C11 C13 C14 C6 0.1(15) 2_567 . . 2_567 ?
C7 C14 C15 C8 133(19) 2_567 . . 2_567 ?
C13 C14 C15 C8 132(12) . . . 2_567 ?
C6 C14 C15 C8 130(12) 2_567 . . 2_567 ?
C7 C14 C15 C9 18(16) 2_567 . . 2_567 ?
C8 C14 C15 C9 -115(13) 2_567 . . 2_567 ?
C13 C14 C15 C9 17(6) . . . 2_567 ?
C6 C14 C15 C9 15(5) 2_567 . . 2_567 ?
C7 C14 C15 C16 8(15) 2_567 . . . ?
C8 C14 C15 C16 -125(13) 2_567 . . . ?
C13 C14 C15 C16 6(5) . . . . ?
C6 C14 C15 C16 4(4) 2_567 . . . ?
C8 C14 C15 C7 -133(19) 2_567 . . 2_567 ?
C13 C14 C15 C7 -2(11) . . . 2_567 ?
C6 C14 C15 C7 -3(13) 2_567 . . 2_567 ?
C8 C15 C16 C9 81(17) 2_567 . . 2_567 ?
C14 C15 C16 C9 156(6) . . . 2_567 ?
C7 C15 C16 C9 157(6) 2_567 . . 2_567 ?
C8 C15 C16 C10 -70(17) 2_567 . . 2_567 ?
C9 C15 C16 C10 -151(10) 2_567 . . 2_567 ?
C14 C15 C16 C10 5(7) . . . 2_567 ?
C7 C15 C16 C10 6(6) 2_567 . . 2_567 ?
C8 C15 C16 C17 -77(16) 2_567 . . . ?
C9 C15 C16 C17 -158(7) 2_567 . . . ?
C14 C15 C16 C17 -3(4) . . . . ?
C7 C15 C16 C17 -1(3) 2_567 . . . ?
C9 C15 C16 C8 -81(17) 2_567 . . 2_567 ?
C14 C15 C16 C8 75(15) . . . 2_567 ?
C7 C15 C16 C8 76(15) 2_567 . . 2_567 ?
C8 C15 C16 C11 -78(16) 2_567 . . 2_567 ?
C9 C15 C16 C11 -159(7) 2_567 . . 2_567 ?
C14 C15 C16 C11 -4(3) . . . 2_567 ?
C7 C15 C16 C11 -2(3) 2_567 . . 2_567 ?
C6 C12 C17 C11 179(4) 2_567 . . 2_567 ?
C13 C12 C17 C11 179(4) . . . 2_567 ?
C11 C12 C17 C11 -2(4) . . . 2_567 ?
C12 C12 C17 C11 -2(3) 2_567 . . 2_567 ?
C17 C12 C17 C11 -2(3) 2_567 . . 2_567 ?
C6 C12 C17 C10 -14(8) 2_567 . . 2_567 ?
C11 C12 C17 C10 167(9) 2_567 . . 2_567 ?
C13 C12 C17 C10 -14(8) . . . 2_567 ?
C11 C12 C17 C10 165(7) . . . 2_567 ?
C12 C12 C17 C10 165(7) 2_567 . . 2_567 ?
C17 C12 C17 C10 165(7) 2_567 . . 2_567 ?
C6 C12 C17 C16 3(2) 2_567 . . . ?
C11 C12 C17 C16 -176(4) 2_567 . . . ?
C13 C12 C17 C16 3(2) . . . . ?
C11 C12 C17 C16 -178.2(14) . . . . ?
C12 C12 C17 C16 -177.9(15) 2_567 . . . ?
C17 C12 C17 C16 -177.9(15) 2_567 . . . ?
C6 C12 C17 S1 -179.7(13) 2_567 . . . ?
C11 C12 C17 S1 1(3) 2_567 . . . ?
C13 C12 C17 S1 -179.6(10) . . . . ?
C11 C12 C17 S1 -1.0(13) . . . . ?
C12 C12 C17 S1 -0.7(10) 2_567 . . . ?
C17 C12 C17 S1 -0.7(11) 2_567 . . . ?
C11 C12 C17 C6 -179(4) 2_567 . . 2_567 ?
C13 C12 C17 C6 0.0(12) . . . 2_567 ?
C11 C12 C17 C6 179(2) . . . 2_567 ?
C12 C12 C17 C6 178.9(19) 2_567 . . 2_567 ?
C17 C12 C17 C6 178.9(19) 2_567 . . 2_567 ?
C6 C12 C17 C9 -2(2) 2_567 . . 2_567 ?
C11 C12 C17 C9 178(4) 2_567 . . 2_567 ?
C13 C12 C17 C9 -2.3(19) . . . 2_567 ?
C11 C12 C17 C9 176.2(10) . . . 2_567 ?
C12 C12 C17 C9 176.6(11) 2_567 . . 2_567 ?
C17 C12 C17 C9 176.6(10) 2_567 . . 2_567 ?
C6 C12 C17 C12 -178.9(19) 2_567 . . 2_567 ?
C11 C12 C17 C12 2(3) 2_567 . . 2_567 ?
C13 C12 C17 C12 -178.9(17) . . . 2_567 ?
C11 C12 C17 C12 -0.3(6) . . . 2_567 ?
C17 C12 C17 C12 0.002(1) 2_567 . . 2_567 ?
C9 C16 C17 C11 -114(20) 2_567 . . 2_567 ?
C10 C16 C17 C11 -177(4) 2_567 . . 2_567 ?
C15 C16 C17 C11 -4(5) . . . 2_567 ?
C8 C16 C17 C11 -11(5) 2_567 . . 2_567 ?
C9 C16 C17 C10 63(21) 2_567 . . 2_567 ?
C15 C16 C17 C10 173(3) . . . 2_567 ?
C8 C16 C17 C10 166(3) 2_567 . . 2_567 ?
C11 C16 C17 C10 177(4) 2_567 . . 2_567 ?
C9 C16 C17 C12 -111(21) 2_567 . . . ?
C10 C16 C17 C12 -175(2) 2_567 . . . ?
C15 C16 C17 C12 -2(3) . . . . ?
C8 C16 C17 C12 -9(3) 2_567 . . . ?
C11 C16 C17 C12 2(3) 2_567 . . . ?
C9 C16 C17 S1 72(21) 2_567 . . . ?
C10 C16 C17 S1 8(2) 2_567 . . . ?
C15 C16 C17 S1 -178.9(18) . . . . ?
C8 C16 C17 S1 174.3(14) 2_567 . . . ?
C11 C16 C17 S1 -175(4) 2_567 . . . ?
C9 C16 C17 C6 -110(21) 2_567 . . 2_567 ?
C10 C16 C17 C6 -173(2) 2_567 . . 2_567 ?
C15 C16 C17 C6 -1(2) . . . 2_567 ?
C8 C16 C17 C6 -8(2) 2_567 . . 2_567 ?
C11 C16 C17 C6 4(3) 2_567 . . 2_567 ?
C10 C16 C17 C9 -63(21) 2_567 . . 2_567 ?
C15 C16 C17 C9 109(22) . . . 2_567 ?
C8 C16 C17 C9 102(22) 2_567 . . 2_567 ?
C11 C16 C17 C9 114(20) 2_567 . . 2_567 ?
C13 S1 C17 C11 0.9(17) 2_567 . . 2_567 ?
C6 S1 C17 C11 1.0(16) . . . 2_567 ?
C10 S1 C17 C11 177(2) 2_567 . . 2_567 ?
C12 S1 C17 C11 1.1(15) 2_567 . . 2_567 ?
C13 S1 C17 C10 -176.2(13) 2_567 . . 2_567 ?
C6 S1 C17 C10 -176.1(14) . . . 2_567 ?
C12 S1 C17 C10 -175.9(14) 2_567 . . 2_567 ?
C11 S1 C17 C10 -177(2) 2_567 . . 2_567 ?
C13 S1 C17 C12 0.5(10) 2_567 . . . ?
C6 S1 C17 C12 0.6(10) . . . . ?
C10 S1 C17 C12 176.6(19) 2_567 . . . ?
C12 S1 C17 C12 0.7(10) 2_567 . . . ?
C11 S1 C17 C12 -0.4(12) 2_567 . . . ?
C13 S1 C17 C16 177.6(14) 2_567 . . . ?
C6 S1 C17 C16 177.7(14) . . . . ?
C10 S1 C17 C16 -6.2(15) 2_567 . . . ?
C12 S1 C17 C16 177.9(15) 2_567 . . . ?
C11 S1 C17 C16 177(2) 2_567 . . . ?
C13 S1 C17 C6 0.3(12) 2_567 . . 2_567 ?
C6 S1 C17 C6 0.4(13) . . . 2_567 ?
C10 S1 C17 C6 176(2) 2_567 . . 2_567 ?
C12 S1 C17 C6 0.5(10) 2_567 . . 2_567 ?
C11 S1 C17 C6 -0.6(12) 2_567 . . 2_567 ?
C13 S1 C17 C9 -176.9(9) 2_567 . . 2_567 ?
C6 S1 C17 C9 -176.8(9) . . . 2_567 ?
C10 S1 C17 C9 -0.7(13) 2_567 . . 2_567 ?
C12 S1 C17 C9 -176.6(10) 2_567 . . 2_567 ?
C11 S1 C17 C9 -178(2) 2_567 . . 2_567 ?
C13 S1 C17 C12 -0.2(7) 2_567 . . 2_567 ?
C6 S1 C17 C12 -0.1(5) . . . 2_567 ?
C10 S1 C17 C12 175.9(14) 2_567 . . 2_567 ?
C11 S1 C17 C12 -1.1(15) 2_567 . . 2_567 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C14^a H14A^a S1 0.96 2.96 3.77(3) 142.1 1_554 yes
C9^a H9A^a S1 0.96 2.96 3.70(2) 134.8 1_545 yes

_refine_diff_density_max         0.578
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.079

####################################################################### 
# 
# 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_PHT-TCNB-hb
_audit_block_doi                 10.5517/ccdc.csd.cc241b6r
_database_code_depnum_ccdc_archive 'CCDC 1967483'
loop_
_audit_author_name
_audit_author_address
'Jie Li'
;State Key Laboratory of Chemical Engineering, Tianjin University
China
;
_audit_update_record             
;
2021-03-17 deposited with the CCDC.	2022-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H12 N4'
_chemical_formula_weight         356.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.2228(14)
_cell_length_b                   7.9353(16)
_cell_length_c                   30.653(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.50(3)
_cell_angle_gamma                90
_cell_volume                     1756.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    1773
_cell_measurement_theta_min      3.8155
_cell_measurement_theta_max      27.7910

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.8540
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            19617
_diffrn_reflns_av_unetI/netI     0.0579
_diffrn_reflns_av_R_equivalents  0.0777
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         2.821
_diffrn_reflns_theta_max         27.815
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4158
_reflns_number_gt                2919
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0884P)²+0.2776P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4158
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_gt           0.0630
_refine_ls_wR_factor_ref         0.1705
_refine_ls_wR_factor_gt          0.1516
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.3577(2) 0.5945(2) 0.08078(6) 0.0368(4) Uani 1 1 d . . . . .
N2 N 0.3537(2) 0.1882(2) 0.00048(5) 0.0345(4) Uani 1 1 d . . . . .
N3 N 0.6559(3) -0.3104(2) 0.17151(6) 0.0366(4) Uani 1 1 d . . . . .
N4 N 0.6619(3) 0.0871(3) 0.25102(6) 0.0397(5) Uani 1 1 d . . . . .
C1 C 0.4009(3) 0.4636(3) 0.09353(6) 0.0273(4) Uani 1 1 d . . . . .
C2 C 0.4556(2) 0.3001(2) 0.10997(6) 0.0234(4) Uani 1 1 d . . . . .
C3 C 0.5093(2) 0.2824(3) 0.15388(6) 0.0253(4) Uani 1 1 d . . . . .
H3 H 0.510059 0.377188 0.172802 0.030 Uiso 1 1 calc R U . . .
C4 C 0.5619(2) 0.1242(2) 0.16963(6) 0.0233(4) Uani 1 1 d . . . . .
C5 C 0.5601(2) -0.0162(2) 0.14165(6) 0.0231(4) Uani 1 1 d . . . . .
C6 C 0.5060(2) 0.0010(2) 0.09781(6) 0.0239(4) Uani 1 1 d . . . . .
H6 H 0.504578 -0.094045 0.078946 0.029 Uiso 1 1 calc R U . . .
C7 C 0.4540(2) 0.1597(2) 0.08206(6) 0.0230(4) Uani 1 1 d . . . . .
C8 C 0.3978(3) 0.1772(2) 0.03658(6) 0.0251(4) Uani 1 1 d . . . . .
C9 C 0.6140(3) -0.1800(3) 0.15814(6) 0.0277(4) Uani 1 1 d . . . . .
C10 C 0.6178(3) 0.1040(2) 0.21509(6) 0.0281(4) Uani 1 1 d . . . . .
C11 C -0.0327(2) 0.6833(3) 0.34964(6) 0.0263(4) Uani 1 1 d . . . . .
C12 C -0.0669(3) 0.7762(3) 0.31117(6) 0.0324(5) Uani 1 1 d . . . . .
H12 H -0.043288 0.893965 0.310879 0.039 Uiso 1 1 calc R U . . .
C13 C -0.1347(3) 0.6973(3) 0.27368(7) 0.0373(5) Uani 1 1 d . . . . .
H13 H -0.158000 0.761602 0.247984 0.045 Uiso 1 1 calc R U . . .
C14 C -0.1691(3) 0.5240(3) 0.27337(7) 0.0371(5) Uani 1 1 d . . . . .
H14 H -0.214040 0.471273 0.247356 0.045 Uiso 1 1 calc R U . . .
C15 C -0.1387(3) 0.4294(3) 0.31026(7) 0.0353(5) Uani 1 1 d . . . . .
H15 H -0.163236 0.311754 0.309806 0.042 Uiso 1 1 calc R U . . .
C16 C -0.0700(3) 0.5076(3) 0.34939(6) 0.0291(5) Uani 1 1 d . . . . .
C17 C -0.0412(3) 0.4110(3) 0.38798(7) 0.0338(5) Uani 1 1 d . . . . .
H17 H -0.069156 0.294047 0.387553 0.041 Uiso 1 1 calc R U . . .
C18 C 0.0256(3) 0.4827(3) 0.42560(7) 0.0350(5) Uani 1 1 d . . . . .
H18 H 0.044780 0.414647 0.450818 0.042 Uiso 1 1 calc R U . . .
C19 C 0.0674(3) 0.6591(3) 0.42772(6) 0.0299(5) Uani 1 1 d . . . . .
C20 C 0.1401(3) 0.7332(3) 0.46685(7) 0.0354(5) Uani 1 1 d . . . . .
H20 H 0.160690 0.665397 0.492054 0.043 Uiso 1 1 calc R U . . .
C21 C 0.1805(3) 0.9018(3) 0.46834(7) 0.0379(5) Uani 1 1 d . . . . .
H21 H 0.227328 0.950727 0.494676 0.046 Uiso 1 1 calc R U . . .
C22 C 0.1531(3) 1.0018(3) 0.43139(7) 0.0377(5) Uani 1 1 d . . . . .
H22 H 0.182244 1.118509 0.432589 0.045 Uiso 1 1 calc R U . . .
C23 C 0.0837(3) 0.9322(3) 0.39299(7) 0.0331(5) Uani 1 1 d . . . . .
H23 H 0.066023 1.002211 0.368080 0.040 Uiso 1 1 calc R U . . .
C24 C 0.0390(2) 0.7612(3) 0.39000(6) 0.0264(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.150(3) . ?
N2 C8 1.147(2) . ?
N3 C9 1.151(3) . ?
N4 C10 1.146(2) . ?
C1 C2 1.443(3) . ?
C2 C3 1.398(2) . ?
C2 C7 1.405(3) . ?
C3 C4 1.394(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.406(3) . ?
C4 C10 1.449(3) . ?
C5 C6 1.396(2) . ?
C5 C9 1.445(3) . ?
C6 C7 1.397(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.448(2) . ?
C11 C12 1.407(3) . ?
C11 C16 1.420(3) . ?
C11 C24 1.466(3) . ?
C12 C13 1.387(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.398(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.370(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.428(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.420(3) . ?
C17 C18 1.363(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.434(3) . ?
C18 H18 0.9500 . ?
C19 C24 1.422(3) . ?
C19 C20 1.424(3) . ?
C20 C21 1.370(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.393(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.382(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.398(3) . ?
C23 H23 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 179.4(2) . . ?
C3 C2 C7 120.26(17) . . ?
C3 C2 C1 119.55(17) . . ?
C7 C2 C1 120.19(17) . . ?
C4 C3 C2 119.37(18) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.27(17) . . ?
C3 C4 C10 119.94(17) . . ?
C5 C4 C10 119.79(17) . . ?
C6 C5 C4 120.53(17) . . ?
C6 C5 C9 119.37(17) . . ?
C4 C5 C9 120.10(16) . . ?
C5 C6 C7 119.11(17) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C6 C7 C2 120.46(17) . . ?
C6 C7 C8 119.04(17) . . ?
C2 C7 C8 120.50(17) . . ?
N2 C8 C7 178.9(2) . . ?
N3 C9 C5 179.5(2) . . ?
N4 C10 C4 179.6(2) . . ?
C12 C11 C16 118.76(18) . . ?
C12 C11 C24 122.46(19) . . ?
C16 C11 C24 118.79(18) . . ?
C13 C12 C11 120.5(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.6(2) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 120.6(2) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 120.0(2) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C11 C16 C17 120.11(18) . . ?
C11 C16 C15 119.55(19) . . ?
C17 C16 C15 120.3(2) . . ?
C18 C17 C16 121.4(2) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C19 121.02(19) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C24 C19 C20 119.5(2) . . ?
C24 C19 C18 119.58(19) . . ?
C20 C19 C18 120.9(2) . . ?
C21 C20 C19 120.3(2) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 120.3(2) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C23 C22 C21 120.4(2) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 121.4(2) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C23 C24 C19 118.14(18) . . ?
C23 C24 C11 122.75(18) . . ?
C19 C24 C11 119.11(19) . . ?

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 C2 C3 C4 0.2(3) . . . . ?
C1 C2 C3 C4 179.96(17) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C2 C3 C4 C10 -179.94(16) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C10 C4 C5 C6 179.77(17) . . . . ?
C3 C4 C5 C9 -179.77(17) . . . . ?
C10 C4 C5 C9 -0.1(3) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
C9 C5 C6 C7 179.99(17) . . . . ?
C5 C6 C7 C2 -0.2(3) . . . . ?
C5 C6 C7 C8 -179.96(16) . . . . ?
C3 C2 C7 C6 0.0(3) . . . . ?
C1 C2 C7 C6 -179.75(17) . . . . ?
C3 C2 C7 C8 179.78(16) . . . . ?
C1 C2 C7 C8 0.0(3) . . . . ?
C16 C11 C12 C13 -0.4(3) . . . . ?
C24 C11 C12 C13 179.96(17) . . . . ?
C11 C12 C13 C14 -0.4(3) . . . . ?
C12 C13 C14 C15 0.8(3) . . . . ?
C13 C14 C15 C16 -0.4(3) . . . . ?
C12 C11 C16 C17 -178.48(18) . . . . ?
C24 C11 C16 C17 1.2(3) . . . . ?
C12 C11 C16 C15 0.8(3) . . . . ?
C24 C11 C16 C15 -179.54(16) . . . . ?
C14 C15 C16 C11 -0.4(3) . . . . ?
C14 C15 C16 C17 178.87(18) . . . . ?
C11 C16 C17 C18 -1.3(3) . . . . ?
C15 C16 C17 C18 179.45(18) . . . . ?
C16 C17 C18 C19 0.7(3) . . . . ?
C17 C18 C19 C24 -0.1(3) . . . . ?
C17 C18 C19 C20 -178.96(19) . . . . ?
C24 C19 C20 C21 0.7(3) . . . . ?
C18 C19 C20 C21 179.61(19) . . . . ?
C19 C20 C21 C22 -0.9(3) . . . . ?
C20 C21 C22 C23 0.5(3) . . . . ?
C21 C22 C23 C24 0.1(3) . . . . ?
C22 C23 C24 C19 -0.2(3) . . . . ?
C22 C23 C24 C11 -179.27(18) . . . . ?
C20 C19 C24 C23 -0.2(3) . . . . ?
C18 C19 C24 C23 -179.09(18) . . . . ?
C20 C19 C24 C11 178.92(16) . . . . ?
C18 C19 C24 C11 0.0(3) . . . . ?
C12 C11 C24 C23 -1.8(3) . . . . ?
C16 C11 C24 C23 178.48(18) . . . . ?
C12 C11 C24 C19 179.10(17) . . . . ?
C16 C11 C24 C19 -0.6(3) . . . . ?

_refine_diff_density_max         0.362
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.052

