# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

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

data_312nb_0m
_database_code_depnum_ccdc_archive 'CCDC 2249088'
loop_
_audit_author_name
_audit_author_address
'Wenxiu Yao'
;Ocean University Of China
China
;
_audit_update_record             
;
2023-07-19 deposited with the CCDC.	2024-03-11 downloaded from the CCDC.
;
_audit_creation_date             2023-05-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        1,2,4,5-Tetracyanobenzene-2-Bromofluorene
_chemical_formula_moiety         'C13 H9 Br, C10 H2 N4'
_chemical_formula_sum            'C23 H11 Br N4'
_chemical_formula_weight         423.27
_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'
Br Br -0.2901 2.4595 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.455(3)
_cell_length_b                   7.934(3)
_cell_length_c                   8.270(3)
_cell_angle_alpha                85.443(12)
_cell_angle_beta                 76.787(11)
_cell_angle_gamma                74.123(11)
_cell_volume                     458.0(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1643
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.422
_cell_measurement_theta_min      2.530
_shelx_estimated_absorpt_T_max   0.915
_shelx_estimated_absorpt_T_min   0.822
_exptl_absorpt_coefficient_mu    2.260
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1268 before and 0.0521 after correction.
The Ratio of minimum to maximum transmission is 0.7620.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             212
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0650
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4980
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.479
_diffrn_reflns_theta_min         2.530
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1375
_reflns_number_total             1864
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         1864
_refine_ls_number_restraints     260
_refine_ls_R_factor_all          0.1273
_refine_ls_R_factor_gt           0.0927
_refine_ls_restrained_S_all      1.027
_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)+3.6000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1887
_refine_ls_wR_factor_ref         0.2044
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
Uanis(C6) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C15)
\\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C12) \\sim Ueq,
Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C7)
\\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C17) \\sim Ueq: with sigma of 0.007 and
sigma for terminal atoms of 0.014
4. Others
 Fixed Sof: Br1(0.5) C13(0.5) H13(0.5) C9(0.5) H9A(0.5) H9B(0.5) C14(0.5)
 H14(0.5) C10(0.5) C15(0.5) C11(0.5) H11(0.5) C12(0.5) C17(0.5) H17(0.5)
 C18(0.5) H18(0.5) C16(0.5) C8(0.5) C7(0.5) H7(0.5) C6(0.5) H6(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C13(H13), C14(H14), C11(H11), C17(H17), C18(H18), C7(H7), C6(H6)
5.c Fitted hexagon refined as free rotating group:
 C17(C18,C16,C8,C7,C6)
;
_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
Br1 Br 1.4873(2) -0.3039(3) 1.2078(2) 0.0476(5) Uani 0.5 1 d . U P A -1
N1 N -0.4718(8) 1.1724(8) 0.3231(7) 0.0412(14) Uani 1 1 d . U . . .
N2 N 0.1700(9) 0.4942(7) 0.6162(8) 0.0455(15) Uani 1 1 d . U . . .
C2 C -0.1634(8) 1.0598(7) 0.4364(7) 0.0261(12) Uani 1 1 d . U . . .
C3 C 0.0627(8) 0.8246(8) 0.5383(7) 0.0288(13) Uani 1 1 d . U . . .
C5 C 0.1250(9) 0.6414(9) 0.5786(8) 0.0360(15) Uani 1 1 d . U . . .
C4 C -0.1019(9) 0.8819(8) 0.4725(8) 0.0327(14) Uani 1 1 d . U . . .
H4 H -0.168932 0.802022 0.453270 0.039 Uiso 1 1 calc R U . . .
C1 C -0.3357(9) 1.1240(8) 0.3724(8) 0.0337(14) Uani 1 1 d . U . . .
C13 C 1.161(2) -0.286(2) 1.078(2) 0.035(4) Uani 0.5 1 d . U P A -1
H13 H 1.190685 -0.409549 1.097364 0.042 Uiso 0.5 1 calc R U P A -1
C9 C 1.008(2) 0.267(2) 0.980(2) 0.035(3) Uani 0.5 1 d . U P A -1
H9A H 0.968409 0.341115 1.079322 0.042 Uiso 0.5 1 calc R U P A -1
H9B H 1.105227 0.309358 0.896530 0.042 Uiso 0.5 1 calc R U P A -1
C14 C 1.004(2) -0.196(2) 1.013(2) 0.038(3) Uani 0.5 1 d . U P A -1
H14 H 0.922722 -0.259711 0.987898 0.045 Uiso 0.5 1 calc R U P A -1
C10 C 1.080(2) 0.077(2) 1.0231(19) 0.031(3) Uani 0.5 1 d . U P A -1
C15 C 0.964(2) -0.020(2) 0.9843(19) 0.030(3) Uani 0.5 1 d . U P A -1
C11 C 1.2412(19) -0.0091(18) 1.0895(16) 0.034(2) Uani 0.5 1 d . U P A -1
H11 H 1.322385 0.054172 1.114741 0.041 Uiso 0.5 1 calc R U P A -1
C12 C 1.2756(19) -0.1815(19) 1.1155(16) 0.037(3) Uani 0.5 1 d . U P A -1
C17 C 0.5377(12) 0.2148(13) 0.7944(12) 0.033(3) Uani 0.5 1 d G U P A -1
H17 H 0.434311 0.196497 0.755175 0.040 Uiso 0.5 1 calc R U P A -1
C18 C 0.6617(13) 0.0744(10) 0.8575(11) 0.035(3) Uani 0.5 1 d G U P A -1
H18 H 0.643146 -0.039724 0.861411 0.042 Uiso 0.5 1 calc R U P A -1
C16 C 0.8129(13) 0.1012(11) 0.9149(12) 0.029(2) Uani 0.5 1 d G U P A -1
C8 C 0.8401(13) 0.2682(13) 0.9092(14) 0.031(4) Uani 0.5 1 d G U P A -1
C7 C 0.7160(14) 0.4085(9) 0.8460(13) 0.033(2) Uani 0.5 1 d G U P A -1
H7 H 0.734583 0.522671 0.842133 0.039 Uiso 0.5 1 calc R U P A -1
C6 C 0.5648(12) 0.3818(11) 0.7887(11) 0.033(3) Uani 0.5 1 d G U P A -1
H6 H 0.480030 0.477698 0.745536 0.040 Uiso 0.5 1 calc R 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
Br1 C12 1.900(14) . ?
N1 C1 1.137(8) . ?
N2 C5 1.162(8) . ?
C2 C3 1.388(8) 2_576 ?
C2 C4 1.390(8) . ?
C2 C1 1.450(8) . ?
C3 C5 1.436(9) . ?
C3 C4 1.403(9) . ?
C4 H4 0.9500 . ?
C13 H13 0.9500 . ?
C13 C14 1.40(2) . ?
C13 C12 1.44(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.50(2) . ?
C9 C8 1.492(17) . ?
C14 H14 0.9500 . ?
C14 C15 1.36(2) . ?
C10 C15 1.41(2) . ?
C10 C11 1.417(19) . ?
C15 C16 1.464(17) . ?
C11 H11 0.9500 . ?
C11 C12 1.331(19) . ?
C17 H17 0.9500 . ?
C17 C18 1.3900 . ?
C17 C6 1.3900 . ?
C18 H18 0.9500 . ?
C18 C16 1.3900 . ?
C16 C8 1.3900 . ?
C8 C7 1.3900 . ?
C7 H7 0.9500 . ?
C7 C6 1.3900 . ?
C6 H6 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
C3 C2 C4 120.9(6) 2_576 . ?
C3 C2 C1 120.1(5) 2_576 . ?
C4 C2 C1 119.0(5) . . ?
C2 C3 C5 120.7(6) 2_576 . ?
C2 C3 C4 121.4(6) 2_576 . ?
C4 C3 C5 117.9(6) . . ?
N2 C5 C3 177.6(7) . . ?
C2 C4 C3 117.6(6) . . ?
C2 C4 H4 121.2 . . ?
C3 C4 H4 121.2 . . ?
N1 C1 C2 179.0(7) . . ?
C14 C13 H13 122.0 . . ?
C14 C13 C12 116.0(15) . . ?
C12 C13 H13 122.0 . . ?
H9A C9 H9B 109.2 . . ?
C10 C9 H9A 111.3 . . ?
C10 C9 H9B 111.3 . . ?
C8 C9 H9A 111.3 . . ?
C8 C9 H9B 111.3 . . ?
C8 C9 C10 102.4(12) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 C13 121.6(15) . . ?
C15 C14 H14 119.2 . . ?
C15 C10 C9 110.4(11) . . ?
C15 C10 C11 119.6(13) . . ?
C11 C10 C9 130.0(13) . . ?
C14 C15 C10 120.5(12) . . ?
C14 C15 C16 131.8(13) . . ?
C10 C15 C16 107.7(12) . . ?
C10 C11 H11 121.0 . . ?
C12 C11 C10 118.1(14) . . ?
C12 C11 H11 121.0 . . ?
C13 C12 Br1 115.9(11) . . ?
C11 C12 Br1 119.9(11) . . ?
C11 C12 C13 124.2(14) . . ?
C18 C17 H17 120.0 . . ?
C18 C17 C6 120.0 . . ?
C6 C17 H17 120.0 . . ?
C17 C18 H18 120.0 . . ?
C16 C18 C17 120.0 . . ?
C16 C18 H18 120.0 . . ?
C18 C16 C15 131.6(8) . . ?
C18 C16 C8 120.0 . . ?
C8 C16 C15 108.4(8) . . ?
C16 C8 C9 111.0(9) . . ?
C16 C8 C7 120.0 . . ?
C7 C8 C9 128.9(9) . . ?
C8 C7 H7 120.0 . . ?
C8 C7 C6 120.0 . . ?
C6 C7 H7 120.0 . . ?
C17 C6 H6 120.0 . . ?
C7 C6 C17 120.0 . . ?
C7 C6 H6 120.0 . . ?

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 C3 C4 C2 -1.3(10) 2_576 . . . ?
C3 C2 C4 C3 1.3(10) 2_576 . . . ?
C5 C3 C4 C2 178.9(6) . . . . ?
C1 C2 C4 C3 -178.4(6) . . . . ?
C13 C14 C15 C10 -1(2) . . . . ?
C13 C14 C15 C16 178.7(17) . . . . ?
C9 C10 C15 C14 179.8(18) . . . . ?
C9 C10 C15 C16 -0.1(15) . . . . ?
C9 C10 C11 C12 -179.3(15) . . . . ?
C9 C8 C7 C6 -178.7(14) . . . . ?
C14 C13 C12 Br1 179.1(13) . . . . ?
C14 C13 C12 C11 -1(2) . . . . ?
C14 C15 C16 C18 0(2) . . . . ?
C14 C15 C16 C8 -178.7(16) . . . . ?
C10 C9 C8 C16 1.7(13) . . . . ?
C10 C9 C8 C7 -179.5(9) . . . . ?
C10 C15 C16 C18 -179.7(9) . . . . ?
C10 C15 C16 C8 1.2(11) . . . . ?
C10 C11 C12 Br1 -179.0(10) . . . . ?
C10 C11 C12 C13 1(2) . . . . ?
C15 C10 C11 C12 -1.1(18) . . . . ?
C15 C16 C8 C9 -1.8(11) . . . . ?
C15 C16 C8 C7 179.3(10) . . . . ?
C11 C10 C15 C14 1(2) . . . . ?
C11 C10 C15 C16 -178.6(13) . . . . ?
C12 C13 C14 C15 1(3) . . . . ?
C17 C18 C16 C15 -179.1(13) . . . . ?
C17 C18 C16 C8 0.0 . . . . ?
C18 C17 C6 C7 0.0 . . . . ?
C18 C16 C8 C9 178.9(11) . . . . ?
C18 C16 C8 C7 0.0 . . . . ?
C16 C8 C7 C6 0.0 . . . . ?
C8 C9 C10 C15 -0.9(15) . . . . ?
C8 C9 C10 C11 177.4(14) . . . . ?
C8 C7 C6 C17 0.0 . . . . ?
C6 C17 C18 C16 0.0 . . . . ?


_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_73tcnb1_0m
_database_code_depnum_ccdc_archive 'CCDC 2296351'
loop_
_audit_author_name
_audit_author_address
'Wenxiu Yao'
;Ocean University Of China
China
;
_audit_update_record             
;
2023-09-21 deposited with the CCDC.	2024-03-11 downloaded from the CCDC.
;
_audit_creation_date             2023-07-12
_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        1,2,4,5-Tetracyanobenzene-Fluorene
_chemical_formula_moiety         'C10 H2 N4, C13 H10'
_chemical_formula_sum            'C23 H12 N4'
_chemical_formula_weight         344.37
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1852(5)
_cell_length_b                   7.8039(6)
_cell_length_c                   7.9484(6)
_cell_angle_alpha                73.766(3)
_cell_angle_beta                 83.955(2)
_cell_angle_gamma                88.769(3)
_cell_volume                     425.52(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1933
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.21
_cell_measurement_theta_min      3.71
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5253
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1402 before and 0.0607 after correction. The Ratio of minimum to maximum transmission is 0.7047. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             178
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0562
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5005
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.386
_diffrn_reflns_theta_min         2.851
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1298
_reflns_number_total             1723
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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         0.155
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         1723
_refine_ls_number_restraints     221
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0471
_refine_ls_restrained_S_all      1.006
_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)+(0.0625P)²+0.0717P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1325
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uanis(C17) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C18)
\\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C8) \\sim Ueq,
Uanis(C9) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Others
 Fixed Sof: C7(0.5) H7(0.5) C6(0.5) H6(0.5) C8(0.5) H8(0.5) C11(0.5) C10(0.5)
 C9(0.5) H9(0.5) C12(0.5) H12A(0.5) H12B(0.5) C14(0.5) C15(0.5) H15(0.5)
 C18(0.5) H18(0.5) C13(0.5) C16(0.5) H16(0.5) C17(0.5) H17(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C6(H6), C8(H8), C9(H9), C15(H15), C18(H18), C16(H16), C17(H17)
;
_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 0.6338(2) 0.69317(19) -0.01657(18) 0.0450(4) Uani 1 1 d . U . . .
N2 N 0.3430(2) -0.00884(19) 0.69531(19) 0.0459(4) Uani 1 1 d . U . . .
C4 C 0.5436(2) 0.56857(19) 0.31860(19) 0.0294(4) Uani 1 1 d . U . . .
C2 C 0.4434(2) 0.32223(19) 0.56837(19) 0.0298(4) Uani 1 1 d . U . . .
C1 C 0.3865(2) 0.1383(2) 0.64021(19) 0.0343(4) Uani 1 1 d . U . . .
C5 C 0.5924(2) 0.6397(2) 0.1319(2) 0.0345(4) Uani 1 1 d . U . . .
C3 C 0.4868(2) 0.3918(2) 0.3879(2) 0.0321(4) Uani 1 1 d . U . . .
H3 H 0.477567 0.318303 0.311778 0.038 Uiso 1 1 calc R . . . .
C7 C 0.1569(18) 0.8504(14) 0.1436(11) 0.044(2) Uani 0.5 1 d . U P A -1
H7 H 0.197793 0.936571 0.036226 0.052 Uiso 0.5 1 calc R . P A -1
C6 C 0.1076(15) 0.6810(12) 0.1389(13) 0.051(2) Uani 0.5 1 d . U P A -1
H6 H 0.113669 0.648400 0.031973 0.061 Uiso 0.5 1 calc R . P A -1
C8 C 0.1484(10) 0.8988(9) 0.3012(10) 0.0443(14) Uani 0.5 1 d . U P A -1
H8 H 0.182981 1.016479 0.298205 0.053 Uiso 0.5 1 calc R . P A -1
C11 C 0.0485(7) 0.5614(6) 0.3022(10) 0.0366(12) Uani 0.5 1 d . U P A -1
C10 C 0.0392(6) 0.6070(8) 0.4591(7) 0.0295(11) Uani 0.5 1 d . U P A -1
C9 C 0.0898(7) 0.7763(9) 0.4631(7) 0.0390(11) Uani 0.5 1 d . U P A -1
H9 H 0.085005 0.807726 0.570657 0.047 Uiso 0.5 1 calc R . P A -1
C12 C -0.0094(5) 0.3692(5) 0.3357(5) 0.0423(8) Uani 0.5 1 d . U P A -1
H12A H 0.094085 0.297989 0.298168 0.051 Uiso 0.5 1 calc R . P A -1
H12B H -0.119862 0.359067 0.274312 0.051 Uiso 0.5 1 calc R . P A -1
C14 C -0.0273(6) 0.4512(7) 0.6036(9) 0.0321(10) Uani 0.5 1 d . U P A -1
C15 C -0.0613(8) 0.4319(8) 0.7816(8) 0.0402(12) Uani 0.5 1 d . U P A -1
H15 H -0.042221 0.526842 0.831288 0.048 Uiso 0.5 1 calc R . P A -1
C18 C -0.1243(10) 0.1469(9) 0.6364(10) 0.0461(15) Uani 0.5 1 d . U P A -1
H18 H -0.146693 0.053769 0.585303 0.055 Uiso 0.5 1 calc R . P A -1
C13 C -0.0561(7) 0.3116(10) 0.5333(6) 0.0349(12) Uani 0.5 1 d . U P A -1
C16 C -0.1255(14) 0.2643(11) 0.8841(12) 0.0446(17) Uani 0.5 1 d . U P A -1
H16 H -0.147730 0.245915 1.007842 0.054 Uiso 0.5 1 calc R . P A -1
C17 C -0.1593(18) 0.1218(12) 0.8181(13) 0.044(2) Uani 0.5 1 d . U P A -1
H17 H -0.204766 0.010685 0.894229 0.053 Uiso 0.5 1 calc R . 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 C5 1.145(2) . ?
N2 C1 1.146(2) . ?
C4 C2 1.411(2) 2_666 ?
C4 C5 1.440(2) . ?
C4 C3 1.388(2) . ?
C2 C1 1.439(2) . ?
C2 C3 1.389(2) . ?
C3 H3 0.9500 . ?
C7 H7 0.9500 . ?
C7 C6 1.387(11) . ?
C7 C8 1.401(9) . ?
C6 H6 0.9500 . ?
C6 C11 1.400(10) . ?
C8 H8 0.9500 . ?
C8 C9 1.401(7) . ?
C11 C10 1.384(7) . ?
C11 C12 1.507(6) . ?
C10 C9 1.388(6) . ?
C10 C14 1.468(6) . ?
C9 H9 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.510(6) . ?
C14 C15 1.376(7) . ?
C14 C13 1.384(7) . ?
C15 H15 0.9500 . ?
C15 C16 1.392(9) . ?
C18 H18 0.9500 . ?
C18 C13 1.385(8) . ?
C18 C17 1.398(11) . ?
C16 H16 0.9500 . ?
C16 C17 1.391(11) . ?
C17 H17 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
C2 C4 C5 119.99(13) 2_666 . ?
C3 C4 C2 119.97(13) . 2_666 ?
C3 C4 C5 120.02(13) . . ?
C4 C2 C1 120.03(13) 2_666 . ?
C3 C2 C4 120.04(14) . 2_666 ?
C3 C2 C1 119.93(13) . . ?
N2 C1 C2 178.90(17) . . ?
N1 C5 C4 178.47(18) . . ?
C4 C3 C2 119.98(13) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C6 C7 H7 118.8 . . ?
C6 C7 C8 122.3(8) . . ?
C8 C7 H7 118.8 . . ?
C7 C6 H6 122.2 . . ?
C7 C6 C11 115.6(8) . . ?
C11 C6 H6 122.2 . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 121.0(7) . . ?
C9 C8 H8 119.5 . . ?
C6 C11 C12 126.7(7) . . ?
C10 C11 C6 122.9(5) . . ?
C10 C11 C12 110.4(6) . . ?
C11 C10 C9 121.3(5) . . ?
C11 C10 C14 108.6(8) . . ?
C9 C10 C14 130.1(8) . . ?
C8 C9 H9 121.5 . . ?
C10 C9 C8 116.9(6) . . ?
C10 C9 H9 121.5 . . ?
C11 C12 H12A 111.3 . . ?
C11 C12 H12B 111.3 . . ?
C11 C12 C13 102.1(4) . . ?
H12A C12 H12B 109.2 . . ?
C13 C12 H12A 111.3 . . ?
C13 C12 H12B 111.3 . . ?
C15 C14 C10 130.1(8) . . ?
C15 C14 C13 121.5(6) . . ?
C13 C14 C10 108.4(8) . . ?
C14 C15 H15 122.2 . . ?
C14 C15 C16 115.6(7) . . ?
C16 C15 H15 122.2 . . ?
C13 C18 H18 121.0 . . ?
C13 C18 C17 117.9(6) . . ?
C17 C18 H18 121.0 . . ?
C14 C13 C12 110.5(6) . . ?
C14 C13 C18 122.2(5) . . ?
C18 C13 C12 127.3(7) . . ?
C15 C16 H16 117.7 . . ?
C17 C16 C15 124.6(9) . . ?
C17 C16 H16 117.7 . . ?
C18 C17 H17 121.0 . . ?
C16 C17 C18 118.1(8) . . ?
C16 C17 H17 121.0 . . ?

_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_315tcnb_0m
_database_code_depnum_ccdc_archive 'CCDC 2249089'
loop_
_audit_author_name
_audit_author_address
'Wenxiu Yao'
;Ocean University Of China
China
;
_audit_update_record             
;
2023-07-19 deposited with the CCDC.	2024-03-11 downloaded from the CCDC.
;
_audit_creation_date             2023-03-15
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        1,2,4,5-Tetracyanobenzene-2-Bromocarbazole
_chemical_formula_moiety         'C12 H8 Br N, C10 H2 N4'
_chemical_formula_sum            'C22 H10 Br N5'
_chemical_formula_weight         424.26
_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'
Br Br -0.2901 2.4595 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0699(19)
_cell_length_b                   9.282(2)
_cell_length_c                   12.323(3)
_cell_angle_alpha                79.161(8)
_cell_angle_beta                 78.504(9)
_cell_angle_gamma                84.709(8)
_cell_volume                     886.9(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3682
_cell_measurement_temperature    160
_cell_measurement_theta_max      26.328
_cell_measurement_theta_min      2.571
_shelx_estimated_absorpt_T_max   0.892
_shelx_estimated_absorpt_T_min   0.721
_exptl_absorpt_coefficient_mu    2.335
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1306 before and 0.0576 after correction.
The Ratio of minimum to maximum transmission is 0.7851.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10206
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.432
_diffrn_reflns_theta_min         2.238
_diffrn_ambient_temperature      160
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2913
_reflns_number_total             3606
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.092
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3606
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0444
_refine_ls_restrained_S_all      1.034
_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)+(0.0411P)²+0.7573P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.1025
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C8(H8), C3(H3), C19(H19), C22(H22), C12(H12), C21(H21), C11(H11),
 C13(H13), C14(H14)
;
_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
Br1 Br 0.92100(5) 1.19904(4) 0.64491(3) 0.02977(13) Uani 1 1 d . . . . .
N5 N 0.4294(4) 1.1302(3) 0.5972(2) 0.0278(7) Uani 1 1 d . . . . .
N1 N 0.6984(4) 0.6808(3) 0.6336(2) 0.0249(7) Uani 1 1 d . . . . .
H1 H 0.751345 0.666463 0.566511 0.030 Uiso 1 1 calc R U . . .
N2 N 0.1605(4) 0.4627(3) 0.5688(2) 0.0289(7) Uani 1 1 d . . . . .
N3 N -0.1037(4) 0.4336(3) 0.8826(3) 0.0353(8) Uani 1 1 d . . . . .
C2 C 0.2516(4) 0.9064(3) 0.6910(3) 0.0184(7) Uani 1 1 d . . . . .
C7 C 0.0618(4) 0.6642(3) 0.7887(3) 0.0193(7) Uani 1 1 d . . . . .
C1 C 0.3506(4) 1.0315(4) 0.6399(3) 0.0215(7) Uani 1 1 d . . . . .
N4 N 0.1632(4) 1.1004(3) 0.9170(3) 0.0347(8) Uani 1 1 d . . . . .
C9 C 0.1565(4) 0.8980(3) 0.8005(3) 0.0198(7) Uani 1 1 d . . . . .
C8 C 0.0610(4) 0.7776(3) 0.8485(3) 0.0210(7) Uani 1 1 d . . . . .
H8 H -0.004789 0.772414 0.922109 0.025 Uiso 1 1 calc R U . . .
C3 C 0.2509(4) 0.7930(3) 0.6314(3) 0.0187(7) Uani 1 1 d . . . . .
H3 H 0.315288 0.798539 0.557404 0.022 Uiso 1 1 calc R U . . .
C5 C 0.1582(4) 0.5544(4) 0.6190(3) 0.0220(7) Uani 1 1 d . . . . .
C4 C 0.1567(4) 0.6727(3) 0.6796(3) 0.0188(7) Uani 1 1 d . . . . .
C17 C 0.6094(4) 0.7846(4) 0.7900(3) 0.0210(7) Uani 1 1 d . . . . .
C20 C 0.7942(4) 1.0292(4) 0.7021(3) 0.0238(7) Uani 1 1 d . . . . .
C18 C 0.7107(4) 0.8011(4) 0.6808(3) 0.0216(7) Uani 1 1 d . . . . .
C19 C 0.8043(4) 0.9244(4) 0.6348(3) 0.0250(8) Uani 1 1 d . . . . .
H19 H 0.871142 0.935621 0.561257 0.030 Uiso 1 1 calc R U . . .
C6 C -0.0313(4) 0.5360(4) 0.8412(3) 0.0250(8) Uani 1 1 d . . . . .
C16 C 0.5315(4) 0.6466(4) 0.8064(3) 0.0225(7) Uani 1 1 d . . . . .
C10 C 0.1598(4) 1.0117(4) 0.8643(3) 0.0240(8) Uani 1 1 d . . . . .
C22 C 0.6063(4) 0.8932(4) 0.8547(3) 0.0238(7) Uani 1 1 d . . . . .
H22 H 0.541342 0.882745 0.928770 0.029 Uiso 1 1 calc R U . . .
C12 C 0.3672(4) 0.4346(4) 0.8821(3) 0.0305(8) Uani 1 1 d . . . . .
H12 H 0.290530 0.381450 0.941463 0.037 Uiso 1 1 calc R U . . .
C21 C 0.6985(4) 1.0165(4) 0.8106(3) 0.0267(8) Uani 1 1 d . . . . .
H21 H 0.696421 1.091565 0.853820 0.032 Uiso 1 1 calc R U . . .
C15 C 0.5892(4) 0.5852(4) 0.7086(3) 0.0239(7) Uani 1 1 d . . . . .
C11 C 0.4181(4) 0.5703(4) 0.8945(3) 0.0262(8) Uani 1 1 d . . . . .
H11 H 0.376279 0.609339 0.961336 0.031 Uiso 1 1 calc R U . . .
C13 C 0.4255(5) 0.3780(4) 0.7868(4) 0.0325(9) Uani 1 1 d . . . . .
H13 H 0.389087 0.285537 0.781585 0.039 Uiso 1 1 calc R U . . .
C14 C 0.5378(4) 0.4519(4) 0.6958(3) 0.0292(8) Uani 1 1 d . . . . .
H14 H 0.576683 0.412546 0.628860 0.035 Uiso 1 1 calc R U . . .


_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
Br1 C20 1.903(3) . ?
N5 C1 1.147(4) . ?
N1 H1 0.8800 . ?
N1 C18 1.371(4) . ?
N1 C15 1.389(4) . ?
N2 C5 1.139(4) . ?
N3 C6 1.143(4) . ?
C2 C1 1.441(4) . ?
C2 C9 1.405(4) . ?
C2 C3 1.393(4) . ?
C7 C8 1.393(4) . ?
C7 C4 1.400(4) . ?
C7 C6 1.442(5) . ?
N4 C10 1.146(4) . ?
C9 C8 1.386(4) . ?
C9 C10 1.435(4) . ?
C8 H8 0.9500 . ?
C3 H3 0.9500 . ?
C3 C4 1.380(4) . ?
C5 C4 1.439(4) . ?
C17 C18 1.418(5) . ?
C17 C16 1.441(5) . ?
C17 C22 1.394(5) . ?
C20 C19 1.380(5) . ?
C20 C21 1.394(5) . ?
C18 C19 1.395(5) . ?
C19 H19 0.9500 . ?
C16 C15 1.407(5) . ?
C16 C11 1.397(5) . ?
C22 H22 0.9500 . ?
C22 C21 1.386(5) . ?
C12 H12 0.9500 . ?
C12 C11 1.403(5) . ?
C12 C13 1.357(5) . ?
C21 H21 0.9500 . ?
C15 C14 1.386(5) . ?
C11 H11 0.9500 . ?
C13 H13 0.9500 . ?
C13 C14 1.403(5) . ?
C14 H14 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
C18 N1 H1 125.4 . . ?
C18 N1 C15 109.2(3) . . ?
C15 N1 H1 125.4 . . ?
C9 C2 C1 120.4(3) . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 C9 119.9(3) . . ?
C8 C7 C4 120.1(3) . . ?
C8 C7 C6 119.5(3) . . ?
C4 C7 C6 120.3(3) . . ?
N5 C1 C2 178.6(3) . . ?
C2 C9 C10 120.6(3) . . ?
C8 C9 C2 119.9(3) . . ?
C8 C9 C10 119.4(3) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.8(3) . . ?
C9 C8 H8 120.1 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 119.9 . . ?
N2 C5 C4 178.5(4) . . ?
C7 C4 C5 119.7(3) . . ?
C3 C4 C7 120.1(3) . . ?
C3 C4 C5 120.2(3) . . ?
C18 C17 C16 105.8(3) . . ?
C22 C17 C18 119.0(3) . . ?
C22 C17 C16 135.2(3) . . ?
C19 C20 Br1 118.2(3) . . ?
C19 C20 C21 123.7(3) . . ?
C21 C20 Br1 118.1(2) . . ?
N1 C18 C17 109.3(3) . . ?
N1 C18 C19 128.6(3) . . ?
C19 C18 C17 122.1(3) . . ?
C20 C19 C18 116.2(3) . . ?
C20 C19 H19 121.9 . . ?
C18 C19 H19 121.9 . . ?
N3 C6 C7 179.3(4) . . ?
C15 C16 C17 107.5(3) . . ?
C11 C16 C17 133.6(3) . . ?
C11 C16 C15 118.9(3) . . ?
N4 C10 C9 178.6(4) . . ?
C17 C22 H22 120.1 . . ?
C21 C22 C17 119.8(3) . . ?
C21 C22 H22 120.1 . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C13 C12 C11 121.3(3) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 C20 119.2(3) . . ?
C22 C21 H21 120.4 . . ?
N1 C15 C16 108.2(3) . . ?
C14 C15 N1 129.1(3) . . ?
C14 C15 C16 122.6(3) . . ?
C16 C11 C12 118.5(3) . . ?
C16 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
C12 C13 H13 119.0 . . ?
C12 C13 C14 122.0(3) . . ?
C14 C13 H13 119.0 . . ?
C15 C14 C13 116.7(3) . . ?
C15 C14 H14 121.7 . . ?
C13 C14 H14 121.7 . . ?

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
Br1 C20 C19 C18 179.3(2) . . . . ?
Br1 C20 C21 C22 -179.3(3) . . . . ?
N1 C18 C19 C20 -179.5(3) . . . . ?
N1 C15 C14 C13 179.8(3) . . . . ?
C2 C9 C8 C7 1.0(5) . . . . ?
C2 C3 C4 C7 -0.1(5) . . . . ?
C2 C3 C4 C5 -178.9(3) . . . . ?
C1 C2 C9 C8 179.7(3) . . . . ?
C1 C2 C9 C10 -1.6(5) . . . . ?
C1 C2 C3 C4 179.9(3) . . . . ?
C9 C2 C3 C4 0.1(5) . . . . ?
C8 C7 C4 C3 0.5(5) . . . . ?
C8 C7 C4 C5 179.3(3) . . . . ?
C3 C2 C9 C8 -0.6(5) . . . . ?
C3 C2 C9 C10 178.1(3) . . . . ?
C4 C7 C8 C9 -1.0(5) . . . . ?
C17 C18 C19 C20 0.7(5) . . . . ?
C17 C16 C15 N1 -0.2(4) . . . . ?
C17 C16 C15 C14 -179.6(3) . . . . ?
C17 C16 C11 C12 -179.9(4) . . . . ?
C17 C22 C21 C20 -0.5(5) . . . . ?
C18 N1 C15 C16 -0.4(4) . . . . ?
C18 N1 C15 C14 179.0(4) . . . . ?
C18 C17 C16 C15 0.6(4) . . . . ?
C18 C17 C16 C11 -179.0(4) . . . . ?
C18 C17 C22 C21 1.5(5) . . . . ?
C19 C20 C21 C22 -0.5(5) . . . . ?
C6 C7 C8 C9 177.1(3) . . . . ?
C6 C7 C4 C3 -177.5(3) . . . . ?
C6 C7 C4 C5 1.3(5) . . . . ?
C16 C17 C18 N1 -0.8(4) . . . . ?
C16 C17 C18 C19 179.1(3) . . . . ?
C16 C17 C22 C21 -179.4(4) . . . . ?
C16 C15 C14 C13 -0.9(5) . . . . ?
C10 C9 C8 C7 -177.7(3) . . . . ?
C22 C17 C18 N1 178.5(3) . . . . ?
C22 C17 C18 C19 -1.6(5) . . . . ?
C22 C17 C16 C15 -178.5(4) . . . . ?
C22 C17 C16 C11 1.9(7) . . . . ?
C12 C13 C14 C15 1.1(5) . . . . ?
C21 C20 C19 C18 0.4(5) . . . . ?
C15 N1 C18 C17 0.8(4) . . . . ?
C15 N1 C18 C19 -179.1(3) . . . . ?
C15 C16 C11 C12 0.5(5) . . . . ?
C11 C16 C15 N1 179.5(3) . . . . ?
C11 C16 C15 C14 0.1(5) . . . . ?
C11 C12 C13 C14 -0.5(6) . . . . ?
C13 C12 C11 C16 -0.3(5) . . . . ?


_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_tcnbk_0m_4
_database_code_depnum_ccdc_archive 'CCDC 2296354'
loop_
_audit_author_name
_audit_author_address
'Wenxiu Yao'
;Ocean University Of China
China
;
_audit_update_record             
;
2023-09-21 deposited with the CCDC.	2024-03-11 downloaded from the CCDC.
;
_audit_creation_date             2023-06-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        1,2,4,5-Tetracyanobenzene-Carbazole
_chemical_formula_moiety         'C10 H2 N4, C12 H9 N'
_chemical_formula_sum            'C22 H11 N5'
_chemical_formula_weight         345.36
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0300(5)
_cell_length_b                   7.8302(6)
_cell_length_c                   7.8567(7)
_cell_angle_alpha                73.722(3)
_cell_angle_beta                 88.510(3)
_cell_angle_gamma                84.102(3)
_cell_volume                     412.95(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2637
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.33
_cell_measurement_theta_min      2.91
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.8562
_exptl_absorpt_correction_T_min  0.5623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1134 before and 0.0622 after correction.
 
For component 2:
 wR2(int) was 0.1081 before and 0.0609 after correction.
 The Ratio of minimum to maximum transmission is 0.68.

Final HKLF 4 output contains 7497 reflections, Rint = 0.0609
 (5000 with I > 3sig(I), Rint = 0.0563)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             178
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_number            1679
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.360
_diffrn_reflns_theta_min         2.701
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1304
_reflns_number_total             1679
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         1679
_refine_ls_number_restraints     173
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0646
_refine_ls_restrained_S_all      1.106
_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)+(0.0655P)²+0.2748P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1525
_refine_ls_wR_factor_ref         0.1677
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
All non-hydrogen atoms have similar U: within 2A with sigma of 0.005 and sigma
for terminal atoms of 0.01 within 2A
4. Others
 Fixed Sof: C8(0.5) H8(0.5) C7(0.5) H7(0.5) C6(0.5) H6(0.5) C11(0.5) C10(0.5)
 C9(0.5) H9(0.5) C12(0.5) C17(0.5) N1(0.5) H1(0.5) C13(0.5) H13(0.5) C14(0.5)
 H14(0.5) C15(0.5) H15(0.5) C16(0.5) H16(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C8(H8), C7(H7), C6(H6), C9(H9), N1(H1), C13(H13), C14(H14), C15(H15),
 C16(H16)
5.b Fitted hexagon refined as free rotating group:
 C8(C7,C6,C11,C10,C9)
;
_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
N3 N 0.6557(3) 0.3008(2) 1.0063(2) 0.0349(5) Uani 1 1 d . U . . .
N2 N 0.3414(3) 1.0204(2) 0.3137(3) 0.0389(5) Uani 1 1 d . U . . .
C4 C 0.4477(3) 0.6825(2) 0.4344(3) 0.0233(5) Uani 1 1 d . U . . .
C2 C 0.5561(3) 0.4300(3) 0.6764(2) 0.0227(5) Uani 1 1 d . U . . .
C3 C 0.5040(3) 0.6124(3) 0.6104(3) 0.0248(5) Uani 1 1 d . U . . .
H3 H 0.506876 0.688651 0.685256 0.030 Uiso 1 1 calc R U . . .
C1 C 0.6124(3) 0.3573(3) 0.8600(3) 0.0270(5) Uani 1 1 d . U . . .
C5 C 0.3904(3) 0.8710(3) 0.3661(3) 0.0277(5) Uani 1 1 d . U . . .
C8 C -0.1608(7) 0.7982(7) 0.1243(4) 0.0363(14) Uani 0.5 1 d G U P A -1
H8 H -0.205838 0.865808 0.009835 0.044 Uiso 0.5 1 calc R U P A -1
C7 C -0.1397(7) 0.8830(4) 0.2552(6) 0.0357(14) Uani 0.5 1 d G U P A -1
H7 H -0.170276 1.008637 0.230179 0.043 Uiso 0.5 1 calc R U P A -1
C6 C -0.0738(5) 0.7841(6) 0.4226(5) 0.0299(10) Uani 0.5 1 d G U P A -1
H6 H -0.059391 0.842091 0.512085 0.036 Uiso 0.5 1 calc R U P A -1
C11 C -0.0291(5) 0.6003(6) 0.4592(4) 0.0266(9) Uani 0.5 1 d G U P A -1
C10 C -0.0502(6) 0.5155(4) 0.3283(6) 0.0297(12) Uani 0.5 1 d G U P A -1
C9 C -0.1161(6) 0.6144(7) 0.1609(5) 0.0358(11) Uani 0.5 1 d G U P A -1
H9 H -0.130511 0.556427 0.071401 0.043 Uiso 0.5 1 calc R U P A -1
C12 C 0.0409(8) 0.4615(7) 0.6196(8) 0.0259(10) Uani 0.5 1 d . U P A -1
C17 C 0.0578(7) 0.3058(8) 0.5683(7) 0.0298(10) Uani 0.5 1 d . U P A -1
N1 N 0.0018(5) 0.3361(5) 0.3968(5) 0.0332(8) Uani 0.5 1 d . U P A -1
H1 H -0.000600 0.254417 0.339756 0.040 Uiso 0.5 1 calc R U P A -1
C13 C 0.0896(8) 0.4670(7) 0.7880(8) 0.0314(10) Uani 0.5 1 d . U P A -1
H13 H 0.079556 0.575500 0.820717 0.038 Uiso 0.5 1 calc R U P A -1
C14 C 0.1545(7) 0.3028(9) 0.9067(7) 0.0351(10) Uani 0.5 1 d . U P A -1
H14 H 0.189554 0.299012 1.023741 0.042 Uiso 0.5 1 calc R U P A -1
C15 C 0.1689(10) 0.1442(8) 0.8561(10) 0.0372(13) Uani 0.5 1 d . U P A -1
H15 H 0.212789 0.035397 0.940695 0.045 Uiso 0.5 1 calc R U P A -1
C16 C 0.1221(10) 0.1400(8) 0.6899(10) 0.0343(12) Uani 0.5 1 d . U P A -1
H16 H 0.132089 0.031341 0.657346 0.041 Uiso 0.5 1 calc R 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
N3 C1 1.146(3) . ?
N2 C5 1.145(3) . ?
C4 C2 1.404(3) 2_666 ?
C4 C3 1.389(3) . ?
C4 C5 1.440(3) . ?
C2 C3 1.389(3) . ?
C2 C1 1.444(3) . ?
C3 H3 0.9500 . ?
C8 H8 0.9500 . ?
C8 C7 1.3900 . ?
C8 C9 1.3900 . ?
C7 H7 0.9500 . ?
C7 C6 1.3900 . ?
C6 H6 0.9500 . ?
C6 C11 1.3900 . ?
C11 C10 1.3900 . ?
C11 C12 1.472(5) . ?
C10 C9 1.3900 . ?
C10 N1 1.370(5) . ?
C9 H9 0.9500 . ?
C12 C17 1.381(8) . ?
C12 C13 1.389(8) . ?
C17 N1 1.362(6) . ?
C17 C16 1.417(8) . ?
N1 H1 0.8800 . ?
C13 H13 0.9500 . ?
C13 C14 1.399(7) . ?
C14 H14 0.9500 . ?
C14 C15 1.400(8) . ?
C15 H15 0.9500 . ?
C15 C16 1.365(9) . ?
C16 H16 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
C2 C4 C5 119.92(17) 2_666 . ?
C3 C4 C2 120.25(18) . 2_666 ?
C3 C4 C5 119.83(18) . . ?
C4 C2 C1 120.41(17) 2_666 . ?
C3 C2 C4 120.18(18) . 2_666 ?
C3 C2 C1 119.41(18) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 C4 119.58(18) . . ?
C2 C3 H3 120.2 . . ?
N3 C1 C2 179.3(2) . . ?
N2 C5 C4 178.6(2) . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C7 H7 120.0 . . ?
C6 C7 C8 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C6 H6 120.0 . . ?
C7 C6 C11 120.0 . . ?
C11 C6 H6 120.0 . . ?
C6 C11 C12 132.9(5) . . ?
C10 C11 C6 120.0 . . ?
C10 C11 C12 107.1(5) . . ?
C11 C10 C9 120.0 . . ?
N1 C10 C11 108.8(4) . . ?
N1 C10 C9 131.2(4) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0 . . ?
C10 C9 H9 120.0 . . ?
C17 C12 C11 104.0(6) . . ?
C17 C12 C13 123.0(5) . . ?
C13 C12 C11 133.0(7) . . ?
C12 C17 C16 120.7(5) . . ?
N1 C17 C12 111.6(5) . . ?
N1 C17 C16 127.7(6) . . ?
C10 N1 H1 125.8 . . ?
C17 N1 C10 108.4(3) . . ?
C17 N1 H1 125.8 . . ?
C12 C13 H13 122.0 . . ?
C12 C13 C14 116.0(6) . . ?
C14 C13 H13 122.0 . . ?
C13 C14 H14 119.4 . . ?
C13 C14 C15 121.3(6) . . ?
C15 C14 H14 119.4 . . ?
C14 C15 H15 118.7 . . ?
C16 C15 C14 122.5(6) . . ?
C16 C15 H15 118.7 . . ?
C17 C16 H16 121.7 . . ?
C15 C16 C17 116.6(5) . . ?
C15 C16 H16 121.7 . . ?

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 0.2(3) 2_666 . . . ?
C2 C4 C3 C2 -0.2(3) 2_666 . . . ?
C1 C2 C3 C4 -179.30(18) . . . . ?
C5 C4 C3 C2 178.91(18) . . . . ?
C8 C7 C6 C11 0.0 . . . . ?
C7 C8 C9 C10 0.0 . . . . ?
C7 C6 C11 C10 0.0 . . . . ?
C7 C6 C11 C12 -179.5(4) . . . . ?
C6 C11 C10 C9 0.0 . . . . ?
C6 C11 C10 N1 -179.7(4) . . . . ?
C6 C11 C12 C17 -179.6(4) . . . . ?
C6 C11 C12 C13 -1.5(7) . . . . ?
C11 C10 C9 C8 0.0 . . . . ?
C11 C10 N1 C17 -0.7(4) . . . . ?
C11 C12 C17 N1 -1.3(6) . . . . ?
C11 C12 C17 C16 -179.8(4) . . . . ?
C11 C12 C13 C14 -179.1(5) . . . . ?
C10 C11 C12 C17 0.9(5) . . . . ?
C10 C11 C12 C13 179.0(5) . . . . ?
C9 C8 C7 C6 0.0 . . . . ?
C9 C10 N1 C17 179.6(3) . . . . ?
C12 C11 C10 C9 179.6(3) . . . . ?
C12 C11 C10 N1 -0.1(4) . . . . ?
C12 C17 N1 C10 1.4(5) . . . . ?
C12 C17 C16 C15 -1.3(8) . . . . ?
C12 C13 C14 C15 0.1(9) . . . . ?
C17 C12 C13 C14 -1.2(8) . . . . ?
N1 C10 C9 C8 179.6(5) . . . . ?
N1 C17 C16 C15 -179.4(5) . . . . ?
C13 C12 C17 N1 -179.7(5) . . . . ?
C13 C12 C17 C16 1.9(8) . . . . ?
C13 C14 C15 C16 0.4(10) . . . . ?
C14 C15 C16 C17 0.2(9) . . . . ?
C16 C17 N1 C10 179.6(5) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
