# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_DAT
_database_code_depnum_ccdc_archive 'CCDC 2103753'
loop_
_audit_author_name
_audit_author_address
'Andrew White'
;Imperial College London
United Kingdom
;
_audit_update_record             
;
2021-08-17 deposited with the CCDC.	2021-11-18 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         'C16 H10 N2'
_chemical_formula_sum            'C16 H10 N2'
_chemical_formula_weight         230.26

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                   7.0360(4)
_cell_length_b                   8.4397(5)
_cell_length_c                   18.5162(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.183(5)
_cell_angle_gamma                90
_cell_volume                     1095.03(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    985
_cell_measurement_theta_min      3.7630
_cell_measurement_theta_max      27.2670

_exptl_crystal_description       blocks
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.327
_exptl_crystal_size_mid          0.169
_exptl_crystal_size_min          0.087
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Agilent Xcalibur 3 E'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 16.0382
_diffrn_reflns_number            3720
_diffrn_reflns_av_unetI/netI     0.0647
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.654
_diffrn_reflns_theta_max         28.030
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.825
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.825
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.825
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2190
_reflns_number_gt                1377
_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       'CrysAlisPro, Rigaku OD'
_computing_cell_refinement       'CrysAlisPro, Rigaku OD'
_computing_data_reduction        'CrysAlisPro, Rigaku OD'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2017)'
_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)+(0.0507P)²+0.0783P] 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         2190
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0859
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1209
_refine_ls_wR_factor_gt          0.1008
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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 0.64671(18) 0.70000(16) 0.42963(7) 0.0318(4) Uani 1 1 d . . . . .
C2 C 0.6508(2) 0.77790(18) 0.49270(9) 0.0292(4) Uani 1 1 d . . . . .
C3 C 0.8224(2) 0.8524(2) 0.52160(10) 0.0381(5) Uani 1 1 d . . . . .
H3A H 0.933378 0.845843 0.496097 0.046 Uiso 1 1 calc R U . . .
C4 C 0.8291(3) 0.9325(2) 0.58502(10) 0.0413(5) Uani 1 1 d . . . . .
H4A H 0.944916 0.981414 0.603559 0.050 Uiso 1 1 calc R U . . .
C5 C 0.6661(3) 0.9444(2) 0.62420(9) 0.0418(5) Uani 1 1 d . . . . .
H5A H 0.673916 1.001465 0.668591 0.050 Uiso 1 1 calc R U . . .
C6 C 0.4996(3) 0.8758(2) 0.59936(9) 0.0379(5) Uani 1 1 d . . . . .
H6A H 0.391254 0.885708 0.626160 0.045 Uiso 1 1 calc R U . . .
C7 C 0.4853(2) 0.78862(18) 0.53315(8) 0.0293(4) Uani 1 1 d . . . . .
N8 N 0.32071(18) 0.71822(16) 0.51044(7) 0.0320(4) Uani 1 1 d . . . . .
C9 C 0.3152(2) 0.63674(18) 0.44679(8) 0.0258(4) Uani 1 1 d . . . . .
C10 C 0.1489(2) 0.55861(18) 0.42067(8) 0.0289(4) Uani 1 1 d . . . . .
H10A H 0.040503 0.563530 0.447683 0.035 Uiso 1 1 calc R U . . .
C11 C 0.1371(2) 0.47412(19) 0.35655(8) 0.0279(4) Uani 1 1 d . . . . .
C12 C -0.0324(2) 0.3911(2) 0.32992(9) 0.0357(4) Uani 1 1 d . . . . .
H12A H -0.139999 0.391333 0.357434 0.043 Uiso 1 1 calc R U . . .
C13 C -0.0412(3) 0.31228(19) 0.26609(10) 0.0383(5) Uani 1 1 d . . . . .
H13A H -0.155167 0.258223 0.249277 0.046 Uiso 1 1 calc R U . . .
C14 C 0.1174(2) 0.3093(2) 0.22392(9) 0.0384(5) Uani 1 1 d . . . . .
H14A H 0.108220 0.254837 0.178839 0.046 Uiso 1 1 calc R U . . .
C15 C 0.2812(2) 0.3834(2) 0.24753(9) 0.0347(4) Uani 1 1 d . . . . .
H15A H 0.386667 0.378737 0.218978 0.042 Uiso 1 1 calc R U . . .
C16 C 0.3001(2) 0.46904(18) 0.31464(8) 0.0276(4) Uani 1 1 d . . . . .
C17 C 0.4650(2) 0.54607(19) 0.34001(8) 0.0291(4) Uani 1 1 d . . . . .
H17A H 0.571997 0.542802 0.312207 0.035 Uiso 1 1 calc R U . . .
C18 C 0.4794(2) 0.62906(18) 0.40562(8) 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 C2 1.338(2) . ?
N1 C18 1.3592(19) . ?
C2 C3 1.422(2) . ?
C2 C7 1.443(2) . ?
C3 C4 1.352(2) . ?
C4 C5 1.415(2) . ?
C5 C6 1.350(2) . ?
C6 C7 1.426(2) . ?
C7 N8 1.3352(19) . ?
N8 C9 1.3620(19) . ?
C9 C10 1.391(2) . ?
C9 C18 1.442(2) . ?
C10 C11 1.381(2) . ?
C11 C12 1.432(2) . ?
C11 C16 1.442(2) . ?
C12 C13 1.353(2) . ?
C13 C14 1.419(2) . ?
C14 C15 1.349(2) . ?
C15 C16 1.433(2) . ?
C16 C17 1.375(2) . ?
C17 C18 1.398(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C18 116.84(14) . . ?
N1 C2 C3 119.75(15) . . ?
N1 C2 C7 121.92(14) . . ?
C3 C2 C7 118.32(15) . . ?
C4 C3 C2 120.63(17) . . ?
C3 C4 C5 120.98(17) . . ?
C6 C5 C4 120.90(17) . . ?
C5 C6 C7 120.41(17) . . ?
N8 C7 C6 119.50(15) . . ?
N8 C7 C2 121.75(14) . . ?
C6 C7 C2 118.75(15) . . ?
C7 N8 C9 116.95(13) . . ?
N8 C9 C10 119.82(14) . . ?
N8 C9 C18 121.25(14) . . ?
C10 C9 C18 118.93(15) . . ?
C11 C10 C9 121.81(15) . . ?
C10 C11 C12 122.18(15) . . ?
C10 C11 C16 119.26(14) . . ?
C12 C11 C16 118.56(15) . . ?
C13 C12 C11 120.86(16) . . ?
C12 C13 C14 120.86(16) . . ?
C15 C14 C13 120.32(16) . . ?
C14 C15 C16 121.63(16) . . ?
C17 C16 C15 122.94(15) . . ?
C17 C16 C11 119.31(15) . . ?
C15 C16 C11 117.75(14) . . ?
C16 C17 C18 121.75(14) . . ?
N1 C18 C17 119.83(14) . . ?
N1 C18 C9 121.26(14) . . ?
C17 C18 C9 118.91(14) . . ?

_refine_diff_density_max         0.157
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_TrAT2
_database_code_depnum_ccdc_archive 'CCDC 2103755'
loop_
_audit_author_name
_audit_author_address
'Andrew White'
;Imperial College London
United Kingdom
;
_audit_update_record             
;
2021-08-17 deposited with the CCDC.	2021-11-18 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         'C15 H9 N3'
_chemical_formula_sum            'C15 H9 N3'
_chemical_formula_weight         231.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 '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/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   3.8495(4)
_cell_length_b                   6.0654(7)
_cell_length_c                   22.823(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.759(12)
_cell_angle_gamma                90
_cell_volume                     532.64(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    290
_cell_measurement_theta_min      3.8630
_cell_measurement_theta_max      68.8610

_exptl_crystal_description       'platy needles'
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_F_000             240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.306
_exptl_crystal_size_mid          0.192
_exptl_crystal_size_min          0.009
_exptl_absorpt_coefficient_mu    0.703
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.904
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_measurement_device_type  'Agilent Xcalibur PX Ultra A'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 10.4115
_diffrn_reflns_number            1541
_diffrn_reflns_av_unetI/netI     0.0778
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.876
_diffrn_reflns_theta_max         73.013
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             1007
_reflns_number_gt                539
_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       'CrysAlisPro, Rigaku OD'
_computing_cell_refinement       'CrysAlisPro, Rigaku OD'
_computing_data_reduction        'CrysAlisPro, Rigaku OD'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2017)'
_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)+(0.0879P)²] 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         1007
_refine_ls_number_parameters     84
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1208
_refine_ls_R_factor_gt           0.0724
_refine_ls_wR_factor_ref         0.2357
_refine_ls_wR_factor_gt          0.1750
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_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 0.4890(7) 0.6639(5) 0.43104(14) 0.0542(9) Uani 0.5 1 d . . P A 1
C1' C 0.4890(7) 0.6639(5) 0.43104(14) 0.0542(9) Uani 0.5 1 d . . P A 2
H1' H 0.561177 0.802719 0.416482 0.065 Uiso 0.5 1 calc R U P A 2
C2 C 0.3199(8) 0.5186(6) 0.39539(15) 0.0502(9) Uani 1 1 d . . . . .
C3 C 0.2505(10) 0.5693(7) 0.33582(17) 0.0608(11) Uani 1 1 d . . . . .
H3 H 0.319504 0.708968 0.321375 0.073 Uiso 1 1 calc R U . B 1
C4 C 0.0895(10) 0.4263(7) 0.29861(17) 0.0656(11) Uani 0.701(3) 1 d . . P C 1
H4 H 0.049619 0.463818 0.258555 0.079 Uiso 0.701(3) 1 calc R U P C 1
N4' N 0.0895(10) 0.4263(7) 0.29861(17) 0.0656(11) Uani 0.299(3) 1 d . . P C 2
C5 C -0.0186(11) 0.2195(8) 0.32036(18) 0.0692(11) Uani 0.799(3) 1 d . . P C 1
H5 H -0.136513 0.119621 0.294581 0.083 Uiso 0.799(3) 1 calc R U P C 1
N5' N -0.0186(11) 0.2195(8) 0.32036(18) 0.0692(11) Uani 0.201(3) 1 d . . P C 2
C6 C 0.0415(10) 0.1610(6) 0.37666(17) 0.0590(10) Uani 1 1 d . . . . .
H6 H -0.032287 0.020172 0.389618 0.071 Uiso 1 1 calc R U . C 1
C7 C 0.2118(8) 0.3045(5) 0.41683(16) 0.0494(9) Uani 1 1 d . . . . .
N8 N 0.2722(8) 0.2475(5) 0.47309(15) 0.0528(9) Uani 0.5 1 d . . P D 1
C8' C 0.2722(8) 0.2475(5) 0.47309(15) 0.0528(9) Uani 0.5 1 d . . P D 2
H8' H 0.196872 0.108155 0.486870 0.063 Uiso 0.5 1 calc R U P D 2
C9 C 0.4452(9) 0.3925(6) 0.51123(17) 0.0523(9) 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 C2 1.353(5) . ?
N1 C9 1.377(5) 3_666 ?
C1' C2 1.353(5) . ?
C1' C9 1.377(5) 3_666 ?
C2 C3 1.411(6) . ?
C2 C7 1.453(5) . ?
C3 N4' 1.351(6) . ?
C3 C4 1.351(6) . ?
C4 C5 1.416(6) . ?
N4' N5' 1.416(6) . ?
C5 C6 1.346(6) . ?
N5' C6 1.346(6) . ?
C6 C7 1.411(5) . ?
C7 C8' 1.343(5) . ?
C7 N8 1.343(5) . ?
N8 C9 1.393(6) . ?
C8' C9 1.393(6) . ?
C9 C9 1.468(7) 3_666 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C9 119.0(3) . 3_666 ?
C2 C1' C9 119.0(3) . 3_666 ?
C1' C2 C3 120.7(3) . . ?
N1 C2 C3 120.7(3) . . ?
C1' C2 C7 121.1(3) . . ?
N1 C2 C7 121.1(3) . . ?
C3 C2 C7 118.1(4) . . ?
N4' C3 C2 122.4(4) . . ?
C4 C3 C2 122.4(4) . . ?
C3 C4 C5 118.8(4) . . ?
C3 N4' N5' 118.8(4) . . ?
C6 C5 C4 121.6(4) . . ?
C6 N5' N4' 121.6(4) . . ?
N5' C6 C7 121.4(4) . . ?
C5 C6 C7 121.4(4) . . ?
C8' C7 C6 121.7(3) . . ?
N8 C7 C6 121.7(3) . . ?
C8' C7 C2 120.6(3) . . ?
N8 C7 C2 120.6(3) . . ?
C6 C7 C2 117.7(3) . . ?
C7 N8 C9 120.0(3) . . ?
C7 C8' C9 120.0(3) . . ?
N1 C9 N8 120.8(3) 3_666 . ?
N1 C9 C9 120.5(5) 3_666 3_666 ?
N8 C9 C9 118.7(4) . 3_666 ?
C8' C9 C9 118.7(4) . 3_666 ?

_refine_diff_density_max         0.261
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.070

####################################################################### 
# 
# 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_TrAT1
_database_code_depnum_ccdc_archive 'CCDC 2103754'
loop_
_audit_author_name
_audit_author_address
'Andrew White'
;Imperial College London
United Kingdom
;
_audit_update_record             
;
2021-08-17 deposited with the CCDC.	2021-11-18 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         'C15 H9 N3'
_chemical_formula_sum            'C15 H9 N3'
_chemical_formula_weight         231.25

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      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                   6.0069(10)
_cell_length_b                   7.3094(14)
_cell_length_c                   12.450(2)
_cell_angle_alpha                77.645(16)
_cell_angle_beta                 85.513(14)
_cell_angle_gamma                87.083(15)
_cell_volume                     532.01(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    373
_cell_measurement_theta_min      2.8480
_cell_measurement_theta_max      27.5930

_exptl_crystal_description       shards
_exptl_crystal_colour            'Dark red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_F_000             240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.177
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.059
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Agilent Xcalibur 3 E'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 16.0382
_diffrn_reflns_number            3003
_diffrn_reflns_av_unetI/netI     0.0694
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.855
_diffrn_reflns_theta_max         28.181
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.804
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.804
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.804
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             2091
_reflns_number_gt                915
_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       'CrysAlisPro, Rigaku OD'
_computing_cell_refinement       'CrysAlisPro, Rigaku OD'
_computing_data_reduction        'CrysAlisPro, Rigaku OD'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2017)'
_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)+(0.0874P)²] 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         2091
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1603
_refine_ls_R_factor_gt           0.0698
_refine_ls_wR_factor_ref         0.2135
_refine_ls_wR_factor_gt          0.1560
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_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 0.6901(4) 0.1626(3) 0.5578(2) 0.0301(7) Uani 1 1 d . . . . .
C2 C 0.5223(5) 0.2149(4) 0.6211(3) 0.0281(8) Uani 1 1 d . . . . .
N3 N 0.5500(4) 0.1814(3) 0.7323(2) 0.0344(7) Uani 1 1 d . . . . .
C4 C 0.3855(5) 0.2321(4) 0.7950(3) 0.0404(9) Uani 1 1 d . . . . .
H4A H 0.403374 0.208637 0.871992 0.048 Uiso 1 1 calc R U . . .
C5 C 0.1786(5) 0.3209(4) 0.7571(3) 0.0376(9) Uani 1 1 d . . . . .
H5A H 0.065376 0.353620 0.807965 0.045 Uiso 1 1 calc R U . . .
C6 C 0.1474(5) 0.3570(4) 0.6491(3) 0.0322(8) Uani 1 1 d . . . . .
H6A H 0.012647 0.416762 0.622095 0.039 Uiso 1 1 calc R U . . .
C7 C 0.3190(5) 0.3043(4) 0.5761(3) 0.0285(8) Uani 1 1 d . . . . .
N8 N 0.2916(4) 0.3403(3) 0.4684(2) 0.0312(7) Uani 1 1 d . . . . .
C9 C 0.4623(5) 0.2867(4) 0.4017(3) 0.0276(8) Uani 1 1 d . . . . .
C10 C 0.4429(5) 0.3185(4) 0.2892(3) 0.0303(8) Uani 1 1 d . . . . .
H10A H 0.309657 0.377438 0.259846 0.036 Uiso 1 1 calc R U . . .
C11 C 0.6108(5) 0.2673(4) 0.2183(3) 0.0301(8) Uani 1 1 d . . . . .
C12 C 0.5960(5) 0.2997(4) 0.1027(3) 0.0384(9) Uani 1 1 d . . . . .
H12A H 0.461805 0.354148 0.072166 0.046 Uiso 1 1 calc R U . . .
C13 C 0.7662(5) 0.2559(5) 0.0348(3) 0.0445(10) Uani 1 1 d . . . . .
H13A H 0.752435 0.280922 -0.042481 0.053 Uiso 1 1 calc R U . . .
C14 C 0.9681(5) 0.1712(5) 0.0798(3) 0.0417(10) Uani 1 1 d . . . . .
H14A H 1.088924 0.142243 0.031557 0.050 Uiso 1 1 calc R U . . .
C15 C 0.9897(5) 0.1319(4) 0.1896(3) 0.0348(8) Uani 1 1 d . . . . .
H15A H 1.123649 0.071928 0.217524 0.042 Uiso 1 1 calc R U . . .
C16 C 0.8155(5) 0.1786(4) 0.2640(3) 0.0294(8) Uani 1 1 d . . . . .
C17 C 0.8351(5) 0.1451(4) 0.3761(3) 0.0295(8) Uani 1 1 d . . . . .
H17A H 0.968001 0.085560 0.405461 0.035 Uiso 1 1 calc R U . . .
C18 C 0.6646(5) 0.1965(4) 0.4475(3) 0.0276(8) 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 C2 1.322(3) . ?
N1 C18 1.362(4) . ?
C2 N3 1.376(4) . ?
C2 C7 1.450(4) . ?
N3 C4 1.299(4) . ?
C4 C5 1.438(4) . ?
C5 C6 1.340(4) . ?
C6 C7 1.415(4) . ?
C7 N8 1.331(4) . ?
N8 C9 1.364(4) . ?
C9 C10 1.383(4) . ?
C9 C18 1.450(4) . ?
C10 C11 1.379(4) . ?
C11 C12 1.416(4) . ?
C11 C16 1.458(4) . ?
C12 C13 1.345(4) . ?
C13 C14 1.431(4) . ?
C14 C15 1.351(4) . ?
C15 C16 1.420(4) . ?
C16 C17 1.379(4) . ?
C17 C18 1.393(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
C2 N1 C18 117.1(2) . . ?
N1 C2 N3 116.8(3) . . ?
N1 C2 C7 122.0(3) . . ?
N3 C2 C7 121.3(3) . . ?
C4 N3 C2 117.1(3) . . ?
N3 C4 C5 125.1(3) . . ?
C6 C5 C4 119.3(3) . . ?
C5 C6 C7 118.7(3) . . ?
N8 C7 C6 119.5(3) . . ?
N8 C7 C2 121.9(3) . . ?
C6 C7 C2 118.6(3) . . ?
C7 N8 C9 117.1(2) . . ?
N8 C9 C10 119.8(3) . . ?
N8 C9 C18 120.6(3) . . ?
C10 C9 C18 119.5(3) . . ?
C11 C10 C9 122.0(3) . . ?
C10 C11 C12 123.2(3) . . ?
C10 C11 C16 118.5(3) . . ?
C12 C11 C16 118.3(3) . . ?
C13 C12 C11 122.0(3) . . ?
C12 C13 C14 119.6(3) . . ?
C15 C14 C13 121.1(3) . . ?
C14 C15 C16 121.1(3) . . ?
C17 C16 C15 122.4(3) . . ?
C17 C16 C11 119.7(3) . . ?
C15 C16 C11 117.9(3) . . ?
C16 C17 C18 121.6(3) . . ?
N1 C18 C17 120.1(3) . . ?
N1 C18 C9 121.3(3) . . ?
C17 C18 C9 118.7(3) . . ?

_refine_diff_density_max         0.279
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.070

####################################################################### 
# 
# 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_TrAT2-TCHQ
_database_code_depnum_ccdc_archive 'CCDC 2103756'
loop_
_audit_author_name
_audit_author_address
'Andrew White'
;Imperial College London
United Kingdom
;
_audit_update_record             
;
2021-08-17 deposited with the CCDC.	2021-11-18 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         '2(C15 H9 N3), C6 H2 Cl4 O2'
_chemical_formula_sum            'C36 H20 Cl4 N6 O2'
_chemical_formula_weight         710.38

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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                   20.605(2)
_cell_length_b                   5.1363(6)
_cell_length_c                   14.6410(18)
_cell_angle_alpha                90
_cell_angle_beta                 109.685(12)
_cell_angle_gamma                90
_cell_volume                     1458.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    536
_cell_measurement_theta_min      2.7880
_cell_measurement_theta_max      23.5940

_exptl_crystal_description       needles
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_F_000             724
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.261
_exptl_crystal_size_mid          0.043
_exptl_crystal_size_min          0.019
_exptl_absorpt_coefficient_mu    0.455
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.917
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Agilent Xcalibur 3 E'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 16.0382
_diffrn_reflns_number            5004
_diffrn_reflns_av_unetI/netI     0.1988
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.783
_diffrn_reflns_theta_max         27.852
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.836
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.836
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.836
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2907
_reflns_number_gt                1356
_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       'CrysAlisPro, Rigaku OD'
_computing_cell_refinement       'CrysAlisPro, Rigaku OD'
_computing_data_reduction        'CrysAlisPro, Rigaku OD'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2017)'
_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)+(0.0295P)²] 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_number_reflns         2907
_refine_ls_number_parameters     221
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1752
_refine_ls_R_factor_gt           0.0717
_refine_ls_wR_factor_ref         0.1497
_refine_ls_wR_factor_gt          0.1132
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_restrained_S_all      0.949
_refine_ls_shift/su_max          0.001
_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 0.3448(2) 0.7457(10) 0.3741(3) 0.0200(12) Uani 1 1 d . . . . .
C2 C 0.2863(3) 0.8799(12) 0.3361(4) 0.0175(13) Uani 1 1 d . . . . .
C3 C 0.2829(3) 1.0875(13) 0.2694(4) 0.0224(14) Uani 1 1 d . . . . .
H3A H 0.323149 1.123896 0.253837 0.027 Uiso 1 1 calc R U . . .
N4 N 0.2287(2) 1.2295(11) 0.2285(3) 0.0280(13) Uani 1 1 d . . . . .
C5 C 0.1704(3) 1.1767(12) 0.2538(4) 0.0257(15) Uani 1 1 d . . . . .
H5A H 0.130569 1.280281 0.224867 0.031 Uiso 1 1 calc R U . . .
C6 C 0.1668(3) 0.9895(13) 0.3162(4) 0.0237(15) Uani 1 1 d . . . . .
H6A H 0.125486 0.963145 0.330278 0.028 Uiso 1 1 calc R U . . .
C7 C 0.2263(3) 0.8303(12) 0.3611(4) 0.0197(14) Uani 1 1 d . . . . .
N8 N 0.2243(2) 0.6421(10) 0.4238(3) 0.0193(11) Uani 1 1 d . . . . .
C9 C 0.2834(3) 0.5030(12) 0.4632(4) 0.0178(14) Uani 1 1 d . . . . .
C10 C 0.2860(2) 0.3034(12) 0.5293(4) 0.0193(14) Uani 1 1 d . . . . .
H10A H 0.246033 0.264919 0.545266 0.023 Uiso 1 1 calc R U . . .
C11 C 0.3455(2) 0.1609(12) 0.5721(4) 0.0169(13) Uani 1 1 d . . . . .
C12 C 0.3488(3) -0.0401(12) 0.6412(4) 0.0225(15) Uani 1 1 d . . . . .
H12A H 0.309126 -0.079397 0.657872 0.027 Uiso 1 1 calc R U . . .
C13 C 0.4080(3) -0.1754(13) 0.6833(4) 0.0263(15) Uani 1 1 d . . . . .
H13A H 0.409459 -0.306948 0.729503 0.032 Uiso 1 1 calc R U . . .
C14 C 0.4680(3) -0.1223(13) 0.6589(4) 0.0240(14) Uani 1 1 d . . . . .
H14A H 0.508747 -0.220605 0.688330 0.029 Uiso 1 1 calc R U . . .
C15 C 0.4677(3) 0.0665(12) 0.5943(4) 0.0212(14) Uani 1 1 d . . . . .
H15A H 0.508465 0.101891 0.579920 0.025 Uiso 1 1 calc R U . . .
C16 C 0.4061(2) 0.2141(12) 0.5471(4) 0.0169(13) Uani 1 1 d . . . . .
C17 C 0.4035(2) 0.4054(12) 0.4796(3) 0.0169(13) Uani 1 1 d . . . . .
H17A H 0.442905 0.436400 0.461341 0.020 Uiso 1 1 calc R U . . .
C18 C 0.3438(3) 0.5548(12) 0.4375(4) 0.0182(14) Uani 1 1 d . . . . .
C20 C 0.0514(3) 0.4726(12) 0.4576(4) 0.0189(14) Uani 1 1 d . . . . .
O20 O 0.09865(14) 0.4377(7) 0.4123(2) 0.0289(11) Uani 1 1 d D . . . .
H20 H 0.1396(2) 0.5159(14) 0.4411(14) 0.05(2) Uiso 1 1 d D . . . .
C21 C 0.0587(2) 0.6520(12) 0.5318(4) 0.0211(14) Uani 1 1 d . . . . .
Cl21 Cl 0.13256(6) 0.8390(3) 0.57147(11) 0.0301(4) Uani 1 1 d . . . . .
C22 C -0.0078(2) 0.3230(12) 0.4263(4) 0.0188(13) Uani 1 1 d . . . . .
Cl22 Cl -0.01703(7) 0.1059(3) 0.33251(10) 0.0303(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 C2 1.336(6) . ?
N1 C18 1.354(7) . ?
C2 C7 1.425(7) . ?
C2 C3 1.432(8) . ?
C3 N4 1.298(7) . ?
N4 C5 1.398(6) . ?
C5 C6 1.346(8) . ?
C6 C7 1.436(7) . ?
C7 N8 1.343(7) . ?
N8 C9 1.363(6) . ?
C9 C10 1.398(7) . ?
C9 C18 1.441(7) . ?
C10 C11 1.382(7) . ?
C11 C12 1.431(7) . ?
C11 C16 1.441(6) . ?
C12 C13 1.358(7) . ?
C13 C14 1.423(7) . ?
C14 C15 1.353(8) . ?
C15 C16 1.439(7) . ?
C16 C17 1.382(7) . ?
C17 C18 1.404(7) . ?
C20 O20 1.361(5) . ?
C20 C22 1.383(7) . ?
C20 C21 1.393(7) . ?
C21 C22 1.388(6) 3_566 ?
C21 Cl21 1.727(5) . ?
C22 Cl22 1.729(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C18 116.1(4) . . ?
N1 C2 C7 122.6(5) . . ?
N1 C2 C3 119.9(5) . . ?
C7 C2 C3 117.4(5) . . ?
N4 C3 C2 124.8(5) . . ?
C3 N4 C5 116.8(5) . . ?
C6 C5 N4 124.6(5) . . ?
C5 C6 C7 118.9(5) . . ?
N8 C7 C2 122.2(5) . . ?
N8 C7 C6 120.3(5) . . ?
C2 C7 C6 117.5(5) . . ?
C7 N8 C9 116.0(4) . . ?
N8 C9 C10 119.9(5) . . ?
N8 C9 C18 121.3(5) . . ?
C10 C9 C18 118.8(5) . . ?
C11 C10 C9 121.5(5) . . ?
C10 C11 C12 121.7(5) . . ?
C10 C11 C16 119.7(5) . . ?
C12 C11 C16 118.5(5) . . ?
C13 C12 C11 120.7(5) . . ?
C12 C13 C14 120.8(6) . . ?
C15 C14 C13 120.8(5) . . ?
C14 C15 C16 120.6(5) . . ?
C17 C16 C15 122.2(5) . . ?
C17 C16 C11 119.2(5) . . ?
C15 C16 C11 118.5(5) . . ?
C16 C17 C18 121.4(5) . . ?
N1 C18 C17 119.0(5) . . ?
N1 C18 C9 121.7(5) . . ?
C17 C18 C9 119.3(5) . . ?
O20 C20 C22 117.5(5) . . ?
O20 C20 C21 124.0(5) . . ?
C22 C20 C21 118.5(4) . . ?
C22 C21 C20 120.5(5) 3_566 . ?
C22 C21 Cl21 120.7(5) 3_566 . ?
C20 C21 Cl21 118.8(4) . . ?
C20 C22 C21 121.1(5) . 3_566 ?
C20 C22 Cl22 118.0(4) . . ?
C21 C22 Cl22 120.9(4) 3_566 . ?

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
O20 H20 N8 0.9000(2) 1.957(12) 2.745(5) 145.3(18) . yes

_refine_diff_density_max         0.420
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.096

