# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

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

data_20190309dh
_database_code_depnum_ccdc_archive 'CCDC 1959736'
loop_
_audit_author_name
_audit_author_address
'Denis Spasyuk'
;Canadian Light Source Inc
Canada
;
_audit_update_record             
;
2019-10-16 deposited with the CCDC.	2019-11-29 downloaded from the CCDC.
;
_audit_creation_date             2019-03-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H8 N4'
_chemical_formula_sum            'C20 H8 N4'
_chemical_formula_weight         304.30
_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 0.0181 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   9.0269(3)
_cell_length_b                   21.7465(7)
_cell_length_c                   7.1992(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.579(2)
_cell_angle_gamma                90
_cell_volume                     1408.72(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4981
_cell_measurement_temperature    173
_cell_measurement_theta_max      71.98
_cell_measurement_theta_min      4.07
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.901
_exptl_absorpt_coefficient_mu    0.709
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9125
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0586 before and 0.0472 after correction. The Ratio of minimum to maximum transmission is 0.9125. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.151
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.046
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11402
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.032
_diffrn_reflns_theta_min         4.066
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2039
_reflns_number_total             2657
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2657
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0490
_refine_ls_restrained_S_all      1.081
_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)+(0.0868P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1282
_refine_ls_wR_factor_ref         0.1384
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C12(H12), 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
C1 C 0.20914(14) 0.69942(6) 0.67359(17) 0.0311(3) Uani 1 1 d . . . . .
C2 C 0.20820(15) 0.76618(6) 0.67244(18) 0.0321(3) Uani 1 1 d . . . . .
C3 C 0.08443(16) 0.79953(6) 0.71700(18) 0.0361(3) Uani 1 1 d . . . . .
H3 H -0.001987 0.778481 0.749643 0.043 Uiso 1 1 calc R . . . .
C4 C 0.08627(17) 0.86348(6) 0.7141(2) 0.0411(4) Uani 1 1 d . . . . .
H4 H 0.000692 0.885873 0.742941 0.049 Uiso 1 1 calc R . . . .
C5 C 0.21228(17) 0.89458(6) 0.66942(19) 0.0406(4) Uani 1 1 d . . . . .
H5 H 0.212704 0.938262 0.669536 0.049 Uiso 1 1 calc R . . . .
C6 C 0.33951(16) 0.86263(6) 0.62391(18) 0.0365(4) Uani 1 1 d . . . . .
C7 C 0.33775(14) 0.79725(6) 0.62428(17) 0.0325(3) Uani 1 1 d . . . . .
C8 C 0.47154(17) 0.89380(6) 0.57722(19) 0.0419(4) Uani 1 1 d . . . . .
H8 H 0.473813 0.937474 0.577885 0.050 Uiso 1 1 calc R . . . .
C9 C 0.59221(17) 0.86251(6) 0.5325(2) 0.0420(4) Uani 1 1 d . . . . .
H9 H 0.677690 0.884602 0.501751 0.050 Uiso 1 1 calc R . . . .
C10 C 0.59482(15) 0.79657(6) 0.53026(18) 0.0356(3) Uani 1 1 d . . . . .
C11 C 0.46671(15) 0.76384(6) 0.57752(17) 0.0323(3) Uani 1 1 d . . . . .
C12 C 0.72002(17) 0.76310(6) 0.4855(2) 0.0406(4) Uani 1 1 d . . . . .
H12 H 0.806216 0.784417 0.453354 0.049 Uiso 1 1 calc R . . . .
C13 C 0.71965(16) 0.69975(6) 0.4876(2) 0.0401(4) Uani 1 1 d . . . . .
H13 H 0.805906 0.678002 0.457807 0.048 Uiso 1 1 calc R . . . .
C14 C 0.59524(15) 0.66727(6) 0.53241(18) 0.0363(3) Uani 1 1 d . . . . .
H14 H 0.596516 0.623591 0.532707 0.044 Uiso 1 1 calc R . . . .
C15 C 0.46858(15) 0.69864(6) 0.57695(17) 0.0320(3) Uani 1 1 d . . . . .
C16 C 0.33597(14) 0.66626(6) 0.62452(17) 0.0313(3) Uani 1 1 d . . . . .
C17 C 0.09058(15) 0.60914(6) 0.72011(18) 0.0345(3) Uani 1 1 d . . . . .
C18 C -0.03776(17) 0.57681(6) 0.7799(2) 0.0403(4) Uani 1 1 d . . . . .
C19 C 0.21346(15) 0.57630(6) 0.66619(18) 0.0343(3) Uani 1 1 d . . . . .
C20 C 0.21014(16) 0.50993(6) 0.6567(2) 0.0404(4) Uani 1 1 d . . . . .
N1 N 0.08683(12) 0.67011(5) 0.72274(15) 0.0339(3) Uani 1 1 d . . . . .
N2 N -0.13642(16) 0.55039(5) 0.8297(2) 0.0542(4) Uani 1 1 d . . . . .
N3 N 0.33603(12) 0.60445(5) 0.61958(15) 0.0335(3) Uani 1 1 d . . . . .
N4 N 0.20168(15) 0.45747(5) 0.6478(2) 0.0540(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
C1 C2 1.4519(18) . ?
C1 C16 1.4213(17) . ?
C1 N1 1.3464(16) . ?
C2 C3 1.3908(18) . ?
C2 C7 1.4174(18) . ?
C3 C4 1.3910(18) . ?
C4 C5 1.383(2) . ?
C5 C6 1.4033(19) . ?
C6 C7 1.4219(18) . ?
C6 C8 1.4342(19) . ?
C7 C11 1.4349(18) . ?
C8 C9 1.345(2) . ?
C9 C10 1.4343(18) . ?
C10 C11 1.4222(18) . ?
C10 C12 1.403(2) . ?
C11 C15 1.4180(18) . ?
C12 C13 1.3778(19) . ?
C13 C14 1.3864(18) . ?
C14 C15 1.3906(17) . ?
C15 C16 1.4531(17) . ?
C16 N3 1.3445(17) . ?
C17 C18 1.4495(18) . ?
C17 C19 1.3999(18) . ?
C17 N1 1.3265(16) . ?
C18 N2 1.1417(18) . ?
C19 C20 1.4451(17) . ?
C19 N3 1.3307(16) . ?
C20 N4 1.1449(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 C1 C2 120.69(11) . . ?
N1 C1 C2 118.05(11) . . ?
N1 C1 C16 121.25(12) . . ?
C3 C2 C1 121.64(12) . . ?
C3 C2 C7 120.11(13) . . ?
C7 C2 C1 118.26(11) . . ?
C2 C3 C4 120.47(13) . . ?
C5 C4 C3 120.22(13) . . ?
C4 C5 C6 121.05(13) . . ?
C5 C6 C7 119.02(12) . . ?
C5 C6 C8 122.11(13) . . ?
C7 C6 C8 118.86(12) . . ?
C2 C7 C6 119.12(12) . . ?
C2 C7 C11 121.11(12) . . ?
C6 C7 C11 119.77(12) . . ?
C9 C8 C6 121.40(13) . . ?
C8 C9 C10 121.52(13) . . ?
C11 C10 C9 118.91(13) . . ?
C12 C10 C9 122.37(13) . . ?
C12 C10 C11 118.71(13) . . ?
C10 C11 C7 119.54(12) . . ?
C15 C11 C7 121.14(11) . . ?
C15 C11 C10 119.33(12) . . ?
C13 C12 C10 120.89(13) . . ?
C12 C13 C14 120.97(13) . . ?
C13 C14 C15 120.00(13) . . ?
C11 C15 C16 118.27(11) . . ?
C14 C15 C11 120.09(12) . . ?
C14 C15 C16 121.64(12) . . ?
C1 C16 C15 120.52(12) . . ?
N3 C16 C1 121.05(11) . . ?
N3 C16 C15 118.43(11) . . ?
C19 C17 C18 120.31(12) . . ?
N1 C17 C18 117.30(11) . . ?
N1 C17 C19 122.38(12) . . ?
N2 C18 C17 178.22(16) . . ?
C17 C19 C20 120.57(12) . . ?
N3 C19 C17 121.90(12) . . ?
N3 C19 C20 117.52(11) . . ?
N4 C20 C19 177.35(15) . . ?
C17 N1 C1 116.55(11) . . ?
C19 N3 C16 116.81(10) . . ?

_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_dth6-96b
_database_code_depnum_ccdc_archive 'CCDC 1959741'
loop_
_audit_author_name
_audit_author_address
'Denis Spasyuk'
;Canadian Light Source Inc
Canada
;
_audit_update_record             
;
2019-10-16 deposited with the CCDC.	2019-11-29 downloaded from the CCDC.
;
_audit_creation_date             2019-04-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C38 H30 N4'
_chemical_formula_sum            'C38 H30 N4'
_chemical_formula_weight         542.66
_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 0.0181 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   8.14050(10)
_cell_length_b                   27.7632(5)
_cell_length_c                   12.0061(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.3970(10)
_cell_angle_gamma                90
_cell_volume                     2712.65(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8379
_cell_measurement_temperature    173
_cell_measurement_theta_max      71.998
_cell_measurement_theta_min      3.183
_shelx_estimated_absorpt_T_max   0.888
_shelx_estimated_absorpt_T_min   0.838
_exptl_absorpt_coefficient_mu    0.609
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.6795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0566 before and 0.0459 after correction. The Ratio of minimum to maximum transmission is 0.9018. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            20606
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.067
_diffrn_reflns_theta_min         3.183
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3953
_reflns_number_total             5112
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 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         0.226
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         5112
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0475
_refine_ls_restrained_S_all      1.013
_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)+(0.0690P)²+1.1083P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1381
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C13(H13), C14(H14),
 C17(H17), C18(H18), C24(H24), C25(H25), C27(H27), C28(H28), C32(H32), C33(H33),
  C35(H35), C36(H36)
2.b Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C37(H37A,H37B,H37C), C38(H38A,H38B,
 H38C)
;
_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 -0.03230(17) 0.31659(6) 0.21763(13) 0.0297(3) Uani 1 1 d . . . . .
N2 N -0.00683(16) 0.21632(5) 0.18169(12) 0.0277(3) Uani 1 1 d . . . . .
N3 N 0.99105(17) 0.47848(6) 0.64388(14) 0.0360(4) Uani 1 1 d . . . . .
N4 N 1.0762(2) 0.05768(8) 0.54234(18) 0.0546(5) Uani 1 1 d . . . . .
C1 C -0.1552(2) 0.29167(7) 0.16582(15) 0.0296(4) Uani 1 1 d . . . . .
C2 C -0.2986(2) 0.31632(8) 0.12841(18) 0.0399(5) Uani 1 1 d . . . . .
H2 H -0.308441 0.350024 0.140182 0.048 Uiso 1 1 calc R . . . .
C3 C -0.4224(2) 0.29160(8) 0.07545(18) 0.0416(5) Uani 1 1 d . . . . .
H3 H -0.517693 0.308368 0.049689 0.050 Uiso 1 1 calc R . . . .
C4 C -0.4108(2) 0.24128(7) 0.05836(16) 0.0345(4) Uani 1 1 d . . . . .
H4 H -0.498656 0.224618 0.021831 0.041 Uiso 1 1 calc R . . . .
C5 C -0.2747(2) 0.21652(7) 0.09388(15) 0.0308(4) Uani 1 1 d . . . . .
H5 H -0.268258 0.182725 0.082366 0.037 Uiso 1 1 calc R . . . .
C6 C -0.14267(19) 0.24120(7) 0.14800(14) 0.0267(4) Uani 1 1 d . . . . .
C7 C 0.10008(19) 0.29194(6) 0.24983(14) 0.0254(3) Uani 1 1 d . . . . .
C8 C 0.23470(19) 0.31771(6) 0.30693(14) 0.0244(3) Uani 1 1 d . . . . .
C9 C 0.2230(2) 0.36677(6) 0.32800(15) 0.0288(4) Uani 1 1 d . . . . .
H9 H 0.126975 0.383803 0.304739 0.035 Uiso 1 1 calc R . . . .
C10 C 0.3496(2) 0.39114(6) 0.38247(15) 0.0295(4) Uani 1 1 d . . . . .
H10 H 0.338607 0.424715 0.395655 0.035 Uiso 1 1 calc R . . . .
C11 C 0.49274(19) 0.36783(6) 0.41847(14) 0.0262(4) Uani 1 1 d . . . . .
C12 C 0.50663(19) 0.31742(6) 0.40043(14) 0.0248(3) Uani 1 1 d . . . . .
C13 C 0.64382(19) 0.28995(6) 0.44308(15) 0.0287(4) Uani 1 1 d . . . . .
H13 H 0.729154 0.305963 0.483799 0.034 Uiso 1 1 calc R . . . .
C14 C 0.65456(19) 0.24198(6) 0.42678(15) 0.0290(4) Uani 1 1 d . . . . .
H14 H 0.747614 0.225145 0.456025 0.035 Uiso 1 1 calc R . . . .
C15 C 0.52947(19) 0.21566(6) 0.36655(14) 0.0254(3) Uani 1 1 d . . . . .
C16 C 0.5427(2) 0.16533(6) 0.34858(14) 0.0281(4) Uani 1 1 d . . . . .
C17 C 0.4208(2) 0.14246(7) 0.28642(16) 0.0343(4) Uani 1 1 d . . . . .
H17 H 0.431452 0.109070 0.270837 0.041 Uiso 1 1 calc R . . . .
C18 C 0.2829(2) 0.16702(7) 0.24608(16) 0.0335(4) Uani 1 1 d . . . . .
H18 H 0.201336 0.150243 0.203508 0.040 Uiso 1 1 calc R . . . .
C19 C 0.2632(2) 0.21575(6) 0.26735(14) 0.0259(4) Uani 1 1 d . . . . .
C20 C 0.11372(19) 0.24119(6) 0.23108(14) 0.0250(3) Uani 1 1 d . . . . .
C21 C 0.38957(19) 0.24108(6) 0.32551(14) 0.0239(3) Uani 1 1 d . . . . .
C22 C 0.37713(18) 0.29234(6) 0.34365(14) 0.0237(3) Uani 1 1 d . . . . .
C23 C 0.62372(19) 0.39632(6) 0.47624(15) 0.0256(3) Uani 1 1 d . . . . .
C24 C 0.58587(19) 0.42729(6) 0.56303(15) 0.0285(4) Uani 1 1 d . . . . .
H24 H 0.474665 0.430068 0.584378 0.034 Uiso 1 1 calc R . . . .
C25 C 0.7044(2) 0.45419(6) 0.61936(15) 0.0288(4) Uani 1 1 d . . . . .
H25 H 0.673219 0.474833 0.678298 0.035 Uiso 1 1 calc R . . . .
C26 C 0.87052(19) 0.45135(6) 0.59050(15) 0.0268(4) Uani 1 1 d . . . . .
C27 C 0.9087(2) 0.42039(7) 0.50266(16) 0.0302(4) Uani 1 1 d . . . . .
H27 H 1.019713 0.417508 0.481002 0.036 Uiso 1 1 calc R . . . .
C28 C 0.7887(2) 0.39390(6) 0.44669(16) 0.0296(4) Uani 1 1 d . . . . .
H28 H 0.818961 0.373612 0.386864 0.036 Uiso 1 1 calc R . . . .
C29 C 0.9561(2) 0.50694(7) 0.74038(17) 0.0382(4) Uani 1 1 d . . . . .
H29A H 0.850237 0.523263 0.729064 0.057 Uiso 1 1 calc GR . . . .
H29B H 1.042912 0.530999 0.752013 0.057 Uiso 1 1 calc GR . . . .
H29C H 0.951229 0.485982 0.805893 0.057 Uiso 1 1 calc GR . . . .
C30 C 1.1630(2) 0.46706(8) 0.62813(19) 0.0428(5) Uani 1 1 d . . . . .
H30A H 1.186692 0.434881 0.657959 0.064 Uiso 1 1 calc GR . . . .
H30B H 1.231987 0.490849 0.667340 0.064 Uiso 1 1 calc GR . . . .
H30C H 1.186327 0.467748 0.548451 0.064 Uiso 1 1 calc GR . . . .
C31 C 0.6832(2) 0.13704(6) 0.39807(15) 0.0279(4) Uani 1 1 d . . . . .
C32 C 0.8251(2) 0.12811(8) 0.34055(17) 0.0376(4) Uani 1 1 d . . . . .
H32 H 0.834174 0.140241 0.266967 0.045 Uiso 1 1 calc R . . . .
C33 C 0.9541(2) 0.10205(8) 0.38707(17) 0.0405(5) Uani 1 1 d . . . . .
H33 H 1.049489 0.096621 0.344755 0.049 Uiso 1 1 calc R . . . .
C34 C 0.9472(2) 0.08354(7) 0.49489(16) 0.0334(4) Uani 1 1 d . . . . .
C35 C 0.8047(2) 0.09287(8) 0.55305(18) 0.0437(5) Uani 1 1 d . . . . .
H35 H 0.795441 0.081145 0.626969 0.052 Uiso 1 1 calc R . . . .
C36 C 0.6761(2) 0.11900(9) 0.50495(18) 0.0434(5) Uani 1 1 d . . . . .
H36 H 0.580401 0.124617 0.546809 0.052 Uiso 1 1 calc R . . . .
C37 C 1.0679(3) 0.03927(11) 0.6534(2) 0.0637(7) Uani 1 1 d . . . . .
H37A H 1.072983 0.066064 0.706562 0.095 Uiso 1 1 calc GR . . . .
H37B H 1.160518 0.017434 0.667997 0.095 Uiso 1 1 calc GR . . . .
H37C H 0.964464 0.021727 0.661814 0.095 Uiso 1 1 calc GR . . . .
C38 C 1.2298(3) 0.05413(13) 0.4892(2) 0.0747(9) Uani 1 1 d . . . . .
H38A H 1.212736 0.041041 0.413969 0.112 Uiso 1 1 calc GR . . . .
H38B H 1.302827 0.032742 0.532376 0.112 Uiso 1 1 calc GR . . . .
H38C H 1.279672 0.086170 0.484489 0.112 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.355(2) . ?
N1 C7 1.326(2) . ?
N2 C6 1.357(2) . ?
N2 C20 1.328(2) . ?
N3 C26 1.382(2) . ?
N3 C29 1.437(2) . ?
N3 C30 1.452(2) . ?
N4 C34 1.383(2) . ?
N4 C37 1.431(3) . ?
N4 C38 1.421(3) . ?
C1 C2 1.417(2) . ?
C1 C6 1.422(3) . ?
C2 C3 1.364(3) . ?
C3 C4 1.415(3) . ?
C4 C5 1.364(2) . ?
C5 C6 1.419(2) . ?
C7 C8 1.465(2) . ?
C7 C20 1.432(2) . ?
C8 C9 1.389(2) . ?
C8 C22 1.418(2) . ?
C9 C10 1.384(2) . ?
C10 C11 1.392(2) . ?
C11 C12 1.421(2) . ?
C11 C23 1.486(2) . ?
C12 C13 1.436(2) . ?
C12 C22 1.423(2) . ?
C13 C14 1.349(3) . ?
C14 C15 1.434(2) . ?
C15 C16 1.418(2) . ?
C15 C21 1.418(2) . ?
C16 C17 1.382(2) . ?
C16 C31 1.498(2) . ?
C17 C18 1.390(2) . ?
C18 C19 1.387(3) . ?
C19 C20 1.464(2) . ?
C19 C21 1.416(2) . ?
C21 C22 1.444(2) . ?
C23 C24 1.391(2) . ?
C23 C28 1.399(2) . ?
C24 C25 1.384(2) . ?
C25 C26 1.406(2) . ?
C26 C27 1.401(3) . ?
C27 C28 1.384(2) . ?
C31 C32 1.383(3) . ?
C31 C36 1.380(3) . ?
C32 C33 1.382(3) . ?
C33 C34 1.395(3) . ?
C34 C35 1.393(3) . ?
C35 C36 1.388(3) . ?

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
C7 N1 C1 117.13(16) . . ?
C20 N2 C6 117.16(15) . . ?
C26 N3 C29 121.42(15) . . ?
C26 N3 C30 119.76(16) . . ?
C29 N3 C30 115.83(15) . . ?
C34 N4 C37 121.09(19) . . ?
C34 N4 C38 121.2(2) . . ?
C38 N4 C37 117.13(18) . . ?
N1 C1 C2 119.49(17) . . ?
N1 C1 C6 121.17(15) . . ?
C2 C1 C6 119.34(16) . . ?
C3 C2 C1 119.90(19) . . ?
C2 C3 C4 120.87(17) . . ?
C5 C4 C3 120.59(16) . . ?
C4 C5 C6 120.03(18) . . ?
N2 C6 C1 121.18(15) . . ?
N2 C6 C5 119.56(16) . . ?
C5 C6 C1 119.26(15) . . ?
N1 C7 C8 118.54(16) . . ?
N1 C7 C20 121.84(15) . . ?
C20 C7 C8 119.62(14) . . ?
C9 C8 C7 120.69(15) . . ?
C9 C8 C22 119.31(15) . . ?
C22 C8 C7 119.98(15) . . ?
C10 C9 C8 120.81(15) . . ?
C9 C10 C11 121.82(16) . . ?
C10 C11 C12 118.66(15) . . ?
C10 C11 C23 118.87(15) . . ?
C12 C11 C23 122.46(14) . . ?
C11 C12 C13 122.18(14) . . ?
C11 C12 C22 119.61(14) . . ?
C22 C12 C13 118.12(15) . . ?
C14 C13 C12 121.66(15) . . ?
C13 C14 C15 121.88(15) . . ?
C16 C15 C14 121.52(15) . . ?
C21 C15 C14 118.43(15) . . ?
C21 C15 C16 120.04(14) . . ?
C15 C16 C31 121.07(14) . . ?
C17 C16 C15 118.61(15) . . ?
C17 C16 C31 120.30(16) . . ?
C16 C17 C18 121.73(17) . . ?
C19 C18 C17 120.70(15) . . ?
C18 C19 C20 121.00(15) . . ?
C18 C19 C21 119.28(15) . . ?
C21 C19 C20 119.72(15) . . ?
N2 C20 C7 121.51(15) . . ?
N2 C20 C19 118.81(16) . . ?
C7 C20 C19 119.68(14) . . ?
C15 C21 C22 119.79(14) . . ?
C19 C21 C15 119.48(15) . . ?
C19 C21 C22 120.73(14) . . ?
C8 C22 C12 119.75(15) . . ?
C8 C22 C21 120.18(14) . . ?
C12 C22 C21 120.05(14) . . ?
C24 C23 C11 120.61(15) . . ?
C24 C23 C28 116.83(15) . . ?
C28 C23 C11 122.57(16) . . ?
C25 C24 C23 122.34(15) . . ?
C24 C25 C26 120.84(16) . . ?
N3 C26 C25 122.09(16) . . ?
N3 C26 C27 121.02(15) . . ?
C27 C26 C25 116.87(15) . . ?
C28 C27 C26 121.65(16) . . ?
C27 C28 C23 121.46(17) . . ?
C32 C31 C16 122.34(17) . . ?
C36 C31 C16 120.67(16) . . ?
C36 C31 C32 116.99(16) . . ?
C33 C32 C31 121.88(18) . . ?
C32 C33 C34 121.35(18) . . ?
N4 C34 C33 121.73(18) . . ?
N4 C34 C35 121.54(18) . . ?
C35 C34 C33 116.72(16) . . ?
C36 C35 C34 121.18(19) . . ?
C31 C36 C35 121.88(18) . . ?

_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_dth6-79a
_database_code_depnum_ccdc_archive 'CCDC 1959737'
loop_
_audit_author_name
_audit_author_address
'Denis Spasyuk'
;Canadian Light Source Inc
Canada
;
_audit_update_record             
;
2019-10-16 deposited with the CCDC.	2019-11-29 downloaded from the CCDC.
;
_audit_creation_date             2019-05-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H12 N2'
_chemical_formula_sum            'C22 H12 N2'
_chemical_formula_weight         304.34
_chemical_absolute_configuration ?
_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 0.0181 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'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   3.8365(2)
_cell_length_b                   18.0157(8)
_cell_length_c                   20.0105(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1383.07(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3246
_cell_measurement_temperature    173
_cell_measurement_theta_max      69.962
_cell_measurement_theta_min      3.301
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.782
_exptl_absorpt_coefficient_mu    0.674
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0870 before and 0.0490 after correction. The Ratio of minimum to maximum transmission is 0.8733. 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    1.462
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.384
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.044
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7153
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.034
_diffrn_reflns_theta_min         3.301
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.642
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                2192
_reflns_number_total             2615
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.5(9)
_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     218
_refine_ls_number_reflns         2615
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0419
_refine_ls_restrained_S_all      1.034
_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)+(0.0592P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1042
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.5(9)
 -0.5(9)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C21(H21), C18(H18), C5(H5), C3(H3), C4(H4), C10(H10), C19(H19), C11(H11),
 C12(H12), C7(H7), C20(H20), C8(H8)
;
_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
N2 N 0.9317(6) 0.71081(11) 0.39831(12) 0.0251(5) Uani 1 1 d . . . . .
N1 N 0.6242(6) 0.58325(11) 0.34101(11) 0.0242(5) Uani 1 1 d . . . . .
C16 C 0.7794(7) 0.77536(14) 0.22631(14) 0.0248(6) Uani 1 1 d . . . . .
C14 C 0.8235(6) 0.70996(13) 0.33540(13) 0.0225(5) Uani 1 1 d . . . . .
C1 C 0.6629(6) 0.64551(14) 0.30624(13) 0.0225(5) Uani 1 1 d . . . . .
C13 C 0.8767(7) 0.77670(14) 0.29430(14) 0.0243(6) Uani 1 1 d . . . . .
C15 C 0.6105(7) 0.71125(14) 0.19768(13) 0.0234(6) Uani 1 1 d . . . . .
C2 C 0.5464(7) 0.64732(14) 0.23691(13) 0.0235(6) Uani 1 1 d . . . . .
C17 C 0.7412(7) 0.58305(14) 0.40458(13) 0.0241(6) Uani 1 1 d . . . . .
C22 C 0.8916(7) 0.64736(14) 0.43428(13) 0.0246(6) Uani 1 1 d . . . . .
C9 C 0.8452(7) 0.83857(14) 0.18556(15) 0.0274(6) Uani 1 1 d . . . . .
C6 C 0.5117(7) 0.71190(14) 0.12935(14) 0.0274(6) Uani 1 1 d . . . . .
C21 C 1.0108(7) 0.64452(15) 0.50096(14) 0.0293(6) Uani 1 1 d . . . . .
H21 H 1.110427 0.687286 0.521121 0.035 Uiso 1 1 calc R . . . .
C18 C 0.7137(7) 0.51730(15) 0.44338(14) 0.0275(6) Uani 1 1 d . . . . .
H18 H 0.612437 0.474004 0.424480 0.033 Uiso 1 1 calc R . . . .
C5 C 0.3419(7) 0.64961(15) 0.10292(14) 0.0301(6) Uani 1 1 d . . . . .
H5 H 0.272364 0.649711 0.057352 0.036 Uiso 1 1 calc R . . . .
C3 C 0.3770(7) 0.58664(14) 0.20845(14) 0.0259(6) Uani 1 1 d . . . . .
H3 H 0.331418 0.543860 0.234795 0.031 Uiso 1 1 calc R . . . .
C4 C 0.2741(7) 0.58817(15) 0.14191(14) 0.0279(6) Uani 1 1 d . . . . .
H4 H 0.156486 0.546695 0.123174 0.033 Uiso 1 1 calc R . . . .
C10 C 1.0006(7) 0.90096(15) 0.21457(15) 0.0316(7) Uani 1 1 d . . . . .
H10 H 1.045641 0.943470 0.187846 0.038 Uiso 1 1 calc R . . . .
C19 C 0.8313(7) 0.51604(15) 0.50719(14) 0.0301(6) Uani 1 1 d . . . . .
H19 H 0.812278 0.471702 0.532639 0.036 Uiso 1 1 calc R . . . .
C11 C 1.0897(7) 0.90179(15) 0.28151(16) 0.0318(7) Uani 1 1 d . . . . .
H11 H 1.190901 0.945030 0.300530 0.038 Uiso 1 1 calc R . . . .
C12 C 1.0319(7) 0.83961(14) 0.32107(15) 0.0289(6) Uani 1 1 d . . . . .
H12 H 1.099051 0.840166 0.366760 0.035 Uiso 1 1 calc R . . . .
C7 C 0.5887(7) 0.77624(15) 0.08970(15) 0.0308(6) Uani 1 1 d . . . . .
H7 H 0.525303 0.776868 0.043808 0.037 Uiso 1 1 calc R . . . .
C20 C 0.9820(8) 0.57991(16) 0.53641(14) 0.0306(6) Uani 1 1 d . . . . .
H20 H 1.064118 0.577910 0.581159 0.037 Uiso 1 1 calc R . . . .
C8 C 0.7499(8) 0.83601(15) 0.11652(15) 0.0322(7) Uani 1 1 d . . . . .
H8 H 0.801089 0.877365 0.088755 0.039 Uiso 1 1 calc R . . . .


_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
N2 C14 1.326(3) . ?
N2 C22 1.360(3) . ?
N1 C1 1.328(3) . ?
N1 C17 1.349(3) . ?
C16 C13 1.411(4) . ?
C16 C15 1.443(3) . ?
C16 C9 1.423(3) . ?
C14 C1 1.438(3) . ?
C14 C13 1.471(3) . ?
C1 C2 1.458(4) . ?
C13 C12 1.388(4) . ?
C15 C2 1.415(3) . ?
C15 C6 1.419(4) . ?
C2 C3 1.393(4) . ?
C17 C22 1.424(3) . ?
C17 C18 1.420(3) . ?
C22 C21 1.411(4) . ?
C9 C10 1.398(4) . ?
C9 C8 1.430(4) . ?
C6 C5 1.401(4) . ?
C6 C7 1.435(4) . ?
C21 C20 1.368(4) . ?
C18 C19 1.355(4) . ?
C5 C4 1.379(4) . ?
C3 C4 1.389(4) . ?
C10 C11 1.382(4) . ?
C19 C20 1.414(4) . ?
C11 C12 1.390(4) . ?
C7 C8 1.353(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
C14 N2 C22 117.2(2) . . ?
C1 N1 C17 117.3(2) . . ?
C13 C16 C15 121.0(2) . . ?
C13 C16 C9 119.5(2) . . ?
C9 C16 C15 119.5(2) . . ?
N2 C14 C1 121.9(2) . . ?
N2 C14 C13 118.5(2) . . ?
C1 C14 C13 119.5(2) . . ?
N1 C1 C14 121.1(2) . . ?
N1 C1 C2 118.9(2) . . ?
C14 C1 C2 120.0(2) . . ?
C16 C13 C14 119.2(2) . . ?
C12 C13 C16 120.0(3) . . ?
C12 C13 C14 120.8(3) . . ?
C2 C15 C16 120.6(2) . . ?
C2 C15 C6 119.7(2) . . ?
C6 C15 C16 119.7(2) . . ?
C15 C2 C1 119.5(2) . . ?
C3 C2 C1 120.9(2) . . ?
C3 C2 C15 119.5(3) . . ?
N1 C17 C22 121.8(2) . . ?
N1 C17 C18 119.5(2) . . ?
C18 C17 C22 118.7(2) . . ?
N2 C22 C17 120.6(2) . . ?
N2 C22 C21 119.6(2) . . ?
C21 C22 C17 119.8(2) . . ?
C16 C9 C8 118.8(3) . . ?
C10 C9 C16 118.7(3) . . ?
C10 C9 C8 122.4(3) . . ?
C15 C6 C7 119.0(3) . . ?
C5 C6 C15 118.8(3) . . ?
C5 C6 C7 122.3(3) . . ?
C20 C21 C22 119.7(3) . . ?
C19 C18 C17 120.3(3) . . ?
C4 C5 C6 121.1(3) . . ?
C4 C3 C2 120.6(3) . . ?
C5 C4 C3 120.3(3) . . ?
C11 C10 C9 121.1(3) . . ?
C18 C19 C20 120.8(3) . . ?
C10 C11 C12 120.2(3) . . ?
C13 C12 C11 120.5(3) . . ?
C8 C7 C6 121.2(3) . . ?
C21 C20 C19 120.7(3) . . ?
C7 C8 C9 121.7(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.5(9)
2 -0.5(9)

####################################################################### 
# 
# 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_DTH696A
_database_code_depnum_ccdc_archive 'CCDC 1959740'
loop_
_audit_author_name
_audit_author_address
'Denis Spasyuk'
;Canadian Light Source Inc
Canada
;
_audit_update_record             
;
2019-10-16 deposited with the CCDC.	2019-11-29 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(C32 H16 N4), C7 H8'
_chemical_formula_sum            'C71 H40 N8'
_chemical_formula_weight         1005.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 '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                   6.9190(14)
_cell_length_b                   17.346(3)
_cell_length_c                   21.688(4)
_cell_angle_alpha                98.88(3)
_cell_angle_beta                 90.98(3)
_cell_angle_gamma                95.88(3)
_cell_volume                     2556.8(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    50695
_cell_measurement_theta_min      0.921
_cell_measurement_theta_max      25.35

_exptl_crystal_description       needle
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_F_000             1044
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.020
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.0238
_exptl_absorpt_correction_T_max  0.0439
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.6889
_diffrn_radiation_type           synchrotron
_diffrn_source                   synchrotron
_diffrn_measurement_device_type  'Rayonix MX300HE CCD area detector'
_diffrn_measurement_method       'κ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8485
_diffrn_reflns_av_unetI/netI     0.1063
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         0.922
_diffrn_reflns_theta_max         23.757
_diffrn_reflns_theta_full        23.757
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             8485
_reflns_number_gt                3857
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'MxDC, (Fodje, 2012)'
_computing_cell_refinement       'XDS (Kabsch (2010)'
_computing_data_reduction        'XDS (Kabsch (2010)'
_computing_structure_solution    'SHELXL2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ShelXle (Hubschle, 2011)'
_computing_publication_material  'LinXTL v. 6.0.0b (Spasyuk, 2009)'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1680P)²+0.0843P] 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         8485
_refine_ls_number_parameters     753
_refine_ls_number_restraints     194
_refine_ls_R_factor_all          0.1356
_refine_ls_R_factor_gt           0.0938
_refine_ls_wR_factor_ref         0.3489
_refine_ls_wR_factor_gt          0.2675
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.059
_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
C1 C 0.7868(7) 0.1860(3) 0.5567(2) 0.1354(13) Uani 1 1 d . . . . .
H1 H 0.790951 0.241466 0.560845 0.162 Uiso 1 1 calc R U . . .
C2 C 0.8164(7) 0.1531(3) 0.6079(3) 0.1343(13) Uani 1 1 d . . . . .
H2 H 0.839761 0.185852 0.647177 0.161 Uiso 1 1 calc R U . . .
C3 C 0.8136(6) 0.0694(3) 0.6046(2) 0.1326(13) Uani 1 1 d . . . . .
C4 C 0.7805(7) 0.0220(3) 0.5450(2) 0.1333(13) Uani 1 1 d . . . . .
C5 C 0.7438(7) 0.0562(3) 0.4903(2) 0.1318(13) Uani 1 1 d . . . . .
C6 C 0.7492(7) 0.1397(3) 0.4959(2) 0.1320(13) Uani 1 1 d . . . . .
C7 C 0.7136(7) 0.1739(3) 0.4423(2) 0.1347(13) Uani 1 1 d . . . . .
C8 C 0.7242(8) 0.2613(3) 0.4446(2) 0.1356(13) Uani 1 1 d . . . . .
C9 C 0.8979(9) 0.3080(3) 0.4602(2) 0.1505(15) Uani 1 1 d . . . . .
H9 H 1.011032 0.284972 0.470062 0.181 Uiso 1 1 calc R U . . .
C10 C 0.9067(10) 0.3887(3) 0.4615(3) 0.1591(17) Uani 1 1 d . . . . .
H10 H 1.026350 0.420545 0.471801 0.191 Uiso 1 1 calc R U . . .
C11 C 0.7417(10) 0.4229(3) 0.4478(3) 0.1560(17) Uani 1 1 d . . . . .
H11 H 0.747276 0.477988 0.448633 0.187 Uiso 1 1 calc R U . . .
C12 C 0.5696(9) 0.3757(3) 0.4330(3) 0.1570(16) Uani 1 1 d . . . . .
H12 H 0.455646 0.398817 0.424224 0.188 Uiso 1 1 calc R U . . .
C13 C 0.5597(8) 0.2954(3) 0.4307(2) 0.1452(15) Uani 1 1 d . . . . .
H13 H 0.440318 0.263662 0.419681 0.174 Uiso 1 1 calc R U . . .
C14 C 0.6667(7) 0.1256(3) 0.3853(2) 0.1385(14) Uani 1 1 d . . . . .
H14 H 0.638187 0.148649 0.349691 0.166 Uiso 1 1 calc R U . . .
C15 C 0.6608(7) 0.0441(3) 0.3794(2) 0.1364(13) Uani 1 1 d . . . . .
H15 H 0.628146 0.012465 0.340110 0.164 Uiso 1 1 calc R U . . .
C16 C 0.7027(7) 0.0087(3) 0.4311(2) 0.1314(13) Uani 1 1 d . . . . .
C17 C 0.7037(7) -0.0762(3) 0.4263(2) 0.1336(13) Uani 1 1 d . . . . .
C18 C 0.6732(7) -0.1985(3) 0.3667(2) 0.1354(13) Uani 1 1 d . . . . .
C19 C 0.6427(8) -0.2460(3) 0.3064(3) 0.1446(15) Uani 1 1 d . . . . .
C20 C 0.7040(7) -0.2314(3) 0.4206(3) 0.1347(13) Uani 1 1 d . . . . .
C21 C 0.7003(8) -0.3155(4) 0.4185(2) 0.1446(15) Uani 1 1 d . . . . .
C22 C 0.7412(7) -0.1095(3) 0.4799(2) 0.1324(13) Uani 1 1 d . . . . .
C23 C 0.7812(7) -0.0612(3) 0.5408(2) 0.1349(13) Uani 1 1 d . . . . .
C24 C 0.8217(7) -0.0942(3) 0.5934(2) 0.1338(13) Uani 1 1 d . . . . .
H24 H 0.828477 -0.149146 0.589782 0.161 Uiso 1 1 calc R U . . .
C25 C 0.8522(7) -0.0471(3) 0.6511(2) 0.1363(13) Uani 1 1 d . . . . .
H25 H 0.877451 -0.070611 0.686806 0.164 Uiso 1 1 calc R U . . .
C26 C 0.8468(7) 0.0338(3) 0.6581(2) 0.1326(13) Uani 1 1 d . . . . .
C27 C 0.8690(7) 0.0803(3) 0.7219(2) 0.1338(13) Uani 1 1 d . . . . .
C28 C 0.7239(8) 0.1245(3) 0.7465(2) 0.1407(14) Uani 1 1 d . . . . .
H28 H 0.611812 0.127355 0.721315 0.169 Uiso 1 1 calc R U . . .
C29 C 0.7402(8) 0.1644(3) 0.8068(3) 0.1452(14) Uani 1 1 d . . . . .
H29 H 0.640875 0.195181 0.822809 0.174 Uiso 1 1 calc R U . . .
C30 C 0.9022(8) 0.1595(3) 0.8442(3) 0.1486(15) Uani 1 1 d . . . . .
H30 H 0.912746 0.186224 0.885942 0.178 Uiso 1 1 calc R U . . .
C31 C 1.0480(8) 0.1158(3) 0.8207(2) 0.1477(15) Uani 1 1 d . . . . .
H31 H 1.159297 0.112993 0.846251 0.177 Uiso 1 1 calc R U . . .
C32 C 1.0321(8) 0.0758(3) 0.7599(2) 0.1421(14) Uani 1 1 d . . . . .
H32 H 1.132050 0.045402 0.743990 0.171 Uiso 1 1 calc R U . . .
C33 C 0.2398(7) 0.4028(3) 0.1238(2) 0.1382(13) Uani 1 1 d . . . . .
H33 H 0.232569 0.390847 0.165089 0.166 Uiso 1 1 calc R U . . .
C34 C 0.2591(7) 0.3449(3) 0.0763(2) 0.1401(14) Uani 1 1 d . . . . .
H34 H 0.265906 0.293135 0.084866 0.168 Uiso 1 1 calc R U . . .
C35 C 0.2699(7) 0.3588(3) 0.0127(2) 0.1358(13) Uani 1 1 d . . . . .
C36 C 0.2612(7) 0.4373(3) 0.0003(2) 0.1357(13) Uani 1 1 d . . . . .
C37 C 0.2382(7) 0.4990(3) 0.0514(2) 0.1374(14) Uani 1 1 d . . . . .
C38 C 0.2296(7) 0.4827(3) 0.1139(2) 0.1373(14) Uani 1 1 d . . . . .
C39 C 0.2079(7) 0.5438(3) 0.1643(2) 0.1370(13) Uani 1 1 d . . . . .
C40 C 0.2167(8) 0.5320(3) 0.2305(2) 0.1395(14) Uani 1 1 d . . . . .
C41 C 0.3828(9) 0.5071(3) 0.2550(3) 0.1468(15) Uani 1 1 d . . . . .
H41 H 0.486255 0.494319 0.228399 0.176 Uiso 1 1 calc R U . . .
C42 C 0.3992(9) 0.5007(3) 0.3184(3) 0.1528(16) Uani 1 1 d . . . . .
H42 H 0.512934 0.483834 0.334879 0.183 Uiso 1 1 calc R U . . .
C43 C 0.2478(11) 0.5191(4) 0.3564(3) 0.1670(18) Uani 1 1 d . . . . .
H43 H 0.258359 0.515372 0.399523 0.200 Uiso 1 1 calc R U . . .
C44 C 0.0822(10) 0.5427(4) 0.3330(3) 0.1666(18) Uani 1 1 d . . . . .
H44 H -0.022232 0.553912 0.359682 0.200 Uiso 1 1 calc R U . . .
C45 C 0.0669(9) 0.5503(3) 0.2702(3) 0.1574(16) Uani 1 1 d . . . . .
H45 H -0.046595 0.568084 0.254361 0.189 Uiso 1 1 calc R U . . .
C46 C 0.1856(7) 0.6187(3) 0.1506(3) 0.1429(14) Uani 1 1 d . . . . .
H46 H 0.165575 0.659465 0.183814 0.171 Uiso 1 1 calc R U . . .
C47 C 0.1919(7) 0.6352(3) 0.0903(3) 0.1414(14) Uani 1 1 d . . . . .
H47 H 0.175702 0.686737 0.082836 0.170 Uiso 1 1 calc R U . . .
C48 C 0.2218(7) 0.5773(3) 0.0402(2) 0.1378(14) Uani 1 1 d . . . . .
C49 C 0.2390(7) 0.5945(3) -0.0224(3) 0.1362(14) Uani 1 1 d . . . . .
C50 C 0.2525(7) 0.6829(3) -0.0910(3) 0.1441(14) Uani 1 1 d . . . . .
C51 C 0.2605(8) 0.7646(4) -0.0989(3) 0.1504(16) Uani 1 1 d . . . . .
C52 C 0.2648(7) 0.6224(3) -0.1407(3) 0.1442(15) Uani 1 1 d . . . . .
C53 C 0.2702(8) 0.6366(3) -0.2041(3) 0.1534(17) Uani 1 1 d . . . . .
C54 C 0.2625(7) 0.5335(3) -0.0729(3) 0.1382(14) Uani 1 1 d . . . . .
C55 C 0.2765(7) 0.4534(3) -0.0620(2) 0.1364(14) Uani 1 1 d . . . . .
C56 C 0.3038(7) 0.3931(3) -0.1108(2) 0.1397(14) Uani 1 1 d . . . . .
H56 H 0.316356 0.403988 -0.152276 0.168 Uiso 1 1 calc R U . . .
C57 C 0.3125(7) 0.3176(3) -0.0986(2) 0.1395(14) Uani 1 1 d . . . . .
H57 H 0.332732 0.277232 -0.132066 0.167 Uiso 1 1 calc R U . . .
C58 C 0.2926(7) 0.2991(3) -0.0389(3) 0.1391(14) Uani 1 1 d . . . . .
C59 C 0.2972(7) 0.2141(3) -0.0301(2) 0.1379(14) Uani 1 1 d . . . . .
C60 C 0.4533(8) 0.1755(3) -0.0515(2) 0.1445(14) Uani 1 1 d . . . . .
H60 H 0.560633 0.203272 -0.068032 0.173 Uiso 1 1 calc R U . . .
C61 C 0.4538(8) 0.0958(3) -0.0488(3) 0.1510(15) Uani 1 1 d . . . . .
H61 H 0.560975 0.069029 -0.063751 0.181 Uiso 1 1 calc R U . . .
C62 C 0.2982(10) 0.0559(3) -0.0243(3) 0.1599(17) Uani 1 1 d . . . . .
H62 H 0.296676 0.001313 -0.023419 0.192 Uiso 1 1 calc R U . . .
C63 C 0.1424(9) 0.0956(3) -0.0009(3) 0.1564(16) Uani 1 1 d . . . . .
H63 H 0.036903 0.068649 0.017208 0.188 Uiso 1 1 calc R U . . .
C64 C 0.1438(8) 0.1746(3) -0.0043(2) 0.1468(15) Uani 1 1 d . . . . .
H64 H 0.038027 0.201845 0.011179 0.176 Uiso 1 1 calc R U . . .
C71A C 0.3289(15) 0.0598(4) 0.1590(4) 0.201(4) Uani 0.822(7) 1 d D . P A 1
H71A H 0.219067 0.025762 0.137100 0.302 Uiso 0.822(7) 1 calc R U P A 1
H71B H 0.400090 0.029793 0.184842 0.302 Uiso 0.822(7) 1 calc R U P A 1
H71C H 0.415972 0.079427 0.128422 0.302 Uiso 0.822(7) 1 calc R U P A 1
C71B C 0.178(4) 0.2920(18) 0.3044(18) 0.188(16) Uani 0.178(7) 1 d D . P A 2
H71D H 0.301879 0.307853 0.327814 0.282 Uiso 0.178(7) 1 calc R U P A 2
H71E H 0.076213 0.279352 0.333116 0.282 Uiso 0.178(7) 1 calc R U P A 2
H71F H 0.143577 0.335077 0.283395 0.282 Uiso 0.178(7) 1 calc R U P A 2
C65A C 0.3819(6) 0.1881(4) 0.2349(3) 0.178(2) Uani 0.822(7) 1 d G U P A 1
H65A H 0.517949 0.186490 0.230837 0.213 Uiso 0.822(7) 1 calc R U P A 1
C66A C 0.3121(8) 0.2489(3) 0.2748(2) 0.183(2) Uani 0.822(7) 1 d G U P A 1
H66A H 0.400506 0.288872 0.298040 0.220 Uiso 0.822(7) 1 calc R U P A 1
C67A C 0.1130(9) 0.2513(3) 0.2808(3) 0.185(2) Uani 0.822(7) 1 d G U P A 1
H67A H 0.065339 0.292851 0.308087 0.222 Uiso 0.822(7) 1 calc R U P A 1
C68A C -0.0163(7) 0.1928(4) 0.2469(3) 0.184(2) Uani 0.822(7) 1 d G U P A 1
H68A H -0.152389 0.194449 0.250930 0.221 Uiso 0.822(7) 1 calc R U P A 1
C69A C 0.0534(8) 0.1320(3) 0.2069(3) 0.181(2) Uani 0.822(7) 1 d G U P A 1
H69A H -0.034951 0.092066 0.183726 0.217 Uiso 0.822(7) 1 calc R U P A 1
C70A C 0.2525(9) 0.1297(3) 0.2010(2) 0.1771(19) Uani 0.822(7) 1 d DG U P A 1
C65B C 0.380(4) 0.1141(17) 0.2109(14) 0.179(3) Uani 0.178(7) 1 d G U P A 2
H65B H 0.498776 0.090613 0.207611 0.215 Uiso 0.178(7) 1 calc R U P A 2
C66B C 0.372(4) 0.1848(17) 0.2504(12) 0.179(3) Uani 0.178(7) 1 d G U P A 2
H66B H 0.483920 0.209562 0.274069 0.215 Uiso 0.178(7) 1 calc R U P A 2
C67B C 0.199(5) 0.2191(13) 0.2552(12) 0.181(2) Uani 0.178(7) 1 d DG U P A 2
C68B C 0.034(4) 0.1828(18) 0.2205(14) 0.182(3) Uani 0.178(7) 1 d G U P A 2
H68B H -0.084098 0.206287 0.223788 0.218 Uiso 0.178(7) 1 calc R U P A 2
C69B C 0.043(4) 0.1121(17) 0.1810(13) 0.181(3) Uani 0.178(7) 1 d G U P A 2
H69B H -0.069246 0.087337 0.157330 0.217 Uiso 0.178(7) 1 calc R U P A 2
C70B C 0.216(5) 0.0778(13) 0.1762(12) 0.180(3) Uani 0.178(7) 1 d G U P A 2
H70B H 0.222189 0.029499 0.149241 0.216 Uiso 0.178(7) 1 calc R U P A 2
N1 N 0.7371(6) -0.1884(2) 0.47640(19) 0.1370(11) Uani 1 1 d . . . . .
N2 N 0.6726(6) -0.1207(3) 0.36924(19) 0.1378(11) Uani 1 1 d . . . . .
N5 N 0.2707(6) 0.5477(3) -0.1323(2) 0.1420(12) Uani 1 1 d . . . . .
N6 N 0.2384(6) 0.6694(3) -0.0320(2) 0.1432(12) Uani 1 1 d . . . . .
N3 N 0.6993(7) -0.3815(3) 0.4190(2) 0.1554(14) Uani 1 1 d . . . . .
N4 N 0.6193(7) -0.2849(3) 0.2582(2) 0.1591(14) Uani 1 1 d . . . . .
N8 N 0.2707(7) 0.8298(3) -0.1034(2) 0.1643(15) Uani 1 1 d . . . . .
N7 N 0.2714(8) 0.6477(3) -0.2550(3) 0.1761(17) 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
C1 C2 1.347(7) . ?
C1 C6 1.439(7) . ?
C1 H1 0.9500 . ?
C2 C3 1.441(6) . ?
C2 H2 0.9500 . ?
C3 C26 1.422(7) . ?
C3 C4 1.423(7) . ?
C4 C23 1.433(6) . ?
C4 C5 1.436(7) . ?
C5 C16 1.422(7) . ?
C5 C6 1.431(7) . ?
C6 C7 1.412(7) . ?
C7 C14 1.396(7) . ?
C7 C8 1.503(7) . ?
C8 C9 1.385(7) . ?
C8 C13 1.385(7) . ?
C9 C10 1.390(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.377(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.380(7) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.396(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.397(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.462(7) . ?
C17 N2 1.354(6) . ?
C17 C22 1.408(7) . ?
C18 N2 1.343(6) . ?
C18 C20 1.401(7) . ?
C18 C19 1.433(7) . ?
C19 N4 1.153(6) . ?
C20 N1 1.323(6) . ?
C20 C21 1.450(8) . ?
C21 N3 1.146(6) . ?
C22 N1 1.357(6) . ?
C22 C23 1.456(7) . ?
C23 C24 1.390(7) . ?
C24 C25 1.385(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.392(6) . ?
C25 H25 0.9500 . ?
C26 C27 1.486(7) . ?
C27 C28 1.389(6) . ?
C27 C32 1.401(7) . ?
C28 C29 1.381(7) . ?
C28 H28 0.9500 . ?
C29 C30 1.390(7) . ?
C29 H29 0.9500 . ?
C30 C31 1.380(7) . ?
C30 H30 0.9500 . ?
C31 C32 1.390(7) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C34 1.343(7) . ?
C33 C38 1.445(7) . ?
C33 H33 0.9500 . ?
C34 C35 1.439(7) . ?
C34 H34 0.9500 . ?
C35 C58 1.425(7) . ?
C35 C36 1.433(7) . ?
C36 C55 1.425(7) . ?
C36 C37 1.440(7) . ?
C37 C38 1.427(7) . ?
C37 C48 1.433(7) . ?
C38 C39 1.421(7) . ?
C39 C46 1.400(7) . ?
C39 C40 1.483(7) . ?
C40 C45 1.389(7) . ?
C40 C41 1.393(7) . ?
C41 C42 1.398(7) . ?
C41 H41 0.9500 . ?
C42 C43 1.377(8) . ?
C42 H42 0.9500 . ?
C43 C44 1.371(8) . ?
C43 H43 0.9500 . ?
C44 C45 1.392(8) . ?
C44 H44 0.9500 . ?
C45 H45 0.9500 . ?
C46 C47 1.383(7) . ?
C46 H46 0.9500 . ?
C47 C48 1.394(7) . ?
C47 H47 0.9500 . ?
C48 C49 1.440(7) . ?
C49 N6 1.346(6) . ?
C49 C54 1.424(7) . ?
C50 N6 1.339(6) . ?
C50 C52 1.395(7) . ?
C50 C51 1.450(8) . ?
C51 N8 1.146(6) . ?
C52 N5 1.339(6) . ?
C52 C53 1.433(9) . ?
C53 N7 1.149(7) . ?
C54 N5 1.350(6) . ?
C54 C55 1.459(7) . ?
C55 C56 1.399(7) . ?
C56 C57 1.382(7) . ?
C56 H56 0.9500 . ?
C57 C58 1.387(7) . ?
C57 H57 0.9500 . ?
C58 C59 1.520(7) . ?
C59 C64 1.377(7) . ?
C59 C60 1.378(7) . ?
C60 C61 1.393(7) . ?
C60 H60 0.9500 . ?
C61 C62 1.378(7) . ?
C61 H61 0.9500 . ?
C62 C63 1.399(8) . ?
C62 H62 0.9500 . ?
C63 C64 1.382(7) . ?
C63 H63 0.9500 . ?
C64 H64 0.9500 . ?
C71A C70A 1.544(7) . ?
C71A H71A 0.9800 . ?
C71A H71B 0.9800 . ?
C71A H71C 0.9800 . ?
C71B C67B 1.543(10) . ?
C71B H71D 0.9800 . ?
C71B H71E 0.9800 . ?
C71B H71F 0.9800 . ?
C65A C66A 1.3900 . ?
C65A C70A 1.3900 . ?
C65A H65A 0.9500 . ?
C66A C67A 1.3900 . ?
C66A H66A 0.9500 . ?
C67A C68A 1.3900 . ?
C67A H67A 0.9500 . ?
C68A C69A 1.3900 . ?
C68A H68A 0.9500 . ?
C69A C70A 1.3900 . ?
C69A H69A 0.9500 . ?
C65B C66B 1.3900 . ?
C65B C70B 1.3900 . ?
C65B H65B 0.9500 . ?
C66B C67B 1.3900 . ?
C66B H66B 0.9500 . ?
C67B C68B 1.3900 . ?
C68B C69B 1.3900 . ?
C68B H68B 0.9500 . ?
C69B C70B 1.3900 . ?
C69B H69B 0.9500 . ?
C70B H70B 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 C1 C6 122.0(5) . . ?
C2 C1 H1 119.0 . . ?
C6 C1 H1 119.0 . . ?
C1 C2 C3 121.7(5) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C26 C3 C4 119.9(4) . . ?
C26 C3 C2 122.4(5) . . ?
C4 C3 C2 117.7(5) . . ?
C3 C4 C23 118.4(5) . . ?
C3 C4 C5 121.1(4) . . ?
C23 C4 C5 120.5(4) . . ?
C16 C5 C6 119.8(5) . . ?
C16 C5 C4 121.2(4) . . ?
C6 C5 C4 119.1(4) . . ?
C7 C6 C5 119.4(4) . . ?
C7 C6 C1 122.1(5) . . ?
C5 C6 C1 118.4(5) . . ?
C14 C7 C6 119.4(5) . . ?
C14 C7 C8 118.5(5) . . ?
C6 C7 C8 122.1(4) . . ?
C9 C8 C13 119.7(5) . . ?
C9 C8 C7 120.4(5) . . ?
C13 C8 C7 119.9(4) . . ?
C8 C9 C10 120.0(5) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 120.4(6) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C10 118.9(5) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 C13 121.2(5) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C12 C13 C8 119.8(5) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?
C7 C14 C15 121.5(5) . . ?
C7 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C14 C15 C16 120.3(5) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C5 119.5(5) . . ?
C15 C16 C17 121.9(5) . . ?
C5 C16 C17 118.7(5) . . ?
N2 C17 C22 121.7(5) . . ?
N2 C17 C16 118.3(5) . . ?
C22 C17 C16 119.9(5) . . ?
N2 C18 C20 121.2(4) . . ?
N2 C18 C19 117.0(5) . . ?
C20 C18 C19 121.8(5) . . ?
N4 C19 C18 179.1(6) . . ?
N1 C20 C18 122.6(5) . . ?
N1 C20 C21 115.8(5) . . ?
C18 C20 C21 121.5(5) . . ?
N3 C21 C20 177.5(6) . . ?
N1 C22 C17 120.5(4) . . ?
N1 C22 C23 117.9(5) . . ?
C17 C22 C23 121.6(5) . . ?
C24 C23 C4 120.5(4) . . ?
C24 C23 C22 121.4(5) . . ?
C4 C23 C22 118.0(5) . . ?
C25 C24 C23 120.1(5) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 121.6(5) . . ?
C24 C25 H25 119.2 . . ?
C26 C25 H25 119.2 . . ?
C25 C26 C3 119.3(4) . . ?
C25 C26 C27 118.9(5) . . ?
C3 C26 C27 121.7(4) . . ?
C28 C27 C32 118.8(5) . . ?
C28 C27 C26 121.0(5) . . ?
C32 C27 C26 120.0(4) . . ?
C29 C28 C27 121.0(5) . . ?
C29 C28 H28 119.5 . . ?
C27 C28 H28 119.5 . . ?
C28 C29 C30 119.8(5) . . ?
C28 C29 H29 120.1 . . ?
C30 C29 H29 120.1 . . ?
C31 C30 C29 120.2(5) . . ?
C31 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?
C30 C31 C32 120.1(5) . . ?
C30 C31 H31 120.0 . . ?
C32 C31 H31 120.0 . . ?
C31 C32 C27 120.2(5) . . ?
C31 C32 H32 119.9 . . ?
C27 C32 H32 119.9 . . ?
C34 C33 C38 121.7(5) . . ?
C34 C33 H33 119.1 . . ?
C38 C33 H33 119.1 . . ?
C33 C34 C35 122.0(5) . . ?
C33 C34 H34 119.0 . . ?
C35 C34 H34 119.0 . . ?
C58 C35 C36 117.9(5) . . ?
C58 C35 C34 123.6(5) . . ?
C36 C35 C34 118.5(4) . . ?
C55 C36 C35 119.8(4) . . ?
C55 C36 C37 120.9(5) . . ?
C35 C36 C37 119.3(5) . . ?
C38 C37 C48 119.1(4) . . ?
C38 C37 C36 120.4(5) . . ?
C48 C37 C36 120.5(5) . . ?
C39 C38 C37 120.4(5) . . ?
C39 C38 C33 121.6(5) . . ?
C37 C38 C33 118.1(4) . . ?
C46 C39 C38 118.3(5) . . ?
C46 C39 C40 118.9(4) . . ?
C38 C39 C40 122.7(5) . . ?
C45 C40 C41 118.8(5) . . ?
C45 C40 C39 121.1(5) . . ?
C41 C40 C39 120.0(4) . . ?
C40 C41 C42 120.8(5) . . ?
C40 C41 H41 119.6 . . ?
C42 C41 H41 119.6 . . ?
C43 C42 C41 118.9(6) . . ?
C43 C42 H42 120.5 . . ?
C41 C42 H42 120.5 . . ?
C44 C43 C42 121.1(6) . . ?
C44 C43 H43 119.4 . . ?
C42 C43 H43 119.4 . . ?
C43 C44 C45 120.0(5) . . ?
C43 C44 H44 120.0 . . ?
C45 C44 H44 120.0 . . ?
C40 C45 C44 120.3(6) . . ?
C40 C45 H45 119.8 . . ?
C44 C45 H45 119.8 . . ?
C47 C46 C39 121.9(5) . . ?
C47 C46 H46 119.0 . . ?
C39 C46 H46 119.0 . . ?
C46 C47 C48 121.0(5) . . ?
C46 C47 H47 119.5 . . ?
C48 C47 H47 119.5 . . ?
C47 C48 C37 119.2(5) . . ?
C47 C48 C49 121.7(5) . . ?
C37 C48 C49 119.1(4) . . ?
N6 C49 C54 120.9(5) . . ?
N6 C49 C48 118.8(5) . . ?
C54 C49 C48 120.3(5) . . ?
N6 C50 C52 121.9(5) . . ?
N6 C50 C51 115.3(5) . . ?
C52 C50 C51 122.8(5) . . ?
N8 C51 C50 177.8(6) . . ?
N5 C52 C50 122.2(5) . . ?
N5 C52 C53 116.1(5) . . ?
C50 C52 C53 121.7(5) . . ?
N7 C53 C52 178.9(7) . . ?
N5 C54 C49 121.2(5) . . ?
N5 C54 C55 117.9(5) . . ?
C49 C54 C55 120.9(5) . . ?
C56 C55 C36 120.1(5) . . ?
C56 C55 C54 121.6(5) . . ?
C36 C55 C54 118.3(4) . . ?
C57 C56 C55 119.7(5) . . ?
C57 C56 H56 120.1 . . ?
C55 C56 H56 120.1 . . ?
C56 C57 C58 121.9(5) . . ?
C56 C57 H57 119.1 . . ?
C58 C57 H57 119.1 . . ?
C57 C58 C35 120.4(5) . . ?
C57 C58 C59 118.4(4) . . ?
C35 C58 C59 121.2(5) . . ?
C64 C59 C60 120.2(5) . . ?
C64 C59 C58 120.9(5) . . ?
C60 C59 C58 118.8(4) . . ?
C59 C60 C61 120.1(5) . . ?
C59 C60 H60 120.0 . . ?
C61 C60 H60 120.0 . . ?
C62 C61 C60 119.7(5) . . ?
C62 C61 H61 120.2 . . ?
C60 C61 H61 120.2 . . ?
C61 C62 C63 120.3(5) . . ?
C61 C62 H62 119.9 . . ?
C63 C62 H62 119.9 . . ?
C64 C63 C62 119.2(5) . . ?
C64 C63 H63 120.4 . . ?
C62 C63 H63 120.4 . . ?
C59 C64 C63 120.6(5) . . ?
C59 C64 H64 119.7 . . ?
C63 C64 H64 119.7 . . ?
C70A C71A H71A 109.5 . . ?
C70A C71A H71B 109.5 . . ?
H71A C71A H71B 109.5 . . ?
C70A C71A H71C 109.5 . . ?
H71A C71A H71C 109.5 . . ?
H71B C71A H71C 109.5 . . ?
C67B C71B H71D 109.5 . . ?
C67B C71B H71E 109.5 . . ?
H71D C71B H71E 109.5 . . ?
C67B C71B H71F 109.5 . . ?
H71D C71B H71F 109.5 . . ?
H71E C71B H71F 109.5 . . ?
C66A C65A C70A 120.0 . . ?
C66A C65A H65A 120.0 . . ?
C70A C65A H65A 120.0 . . ?
C67A C66A C65A 120.0 . . ?
C67A C66A H66A 120.0 . . ?
C65A C66A H66A 120.0 . . ?
C68A C67A C66A 120.0 . . ?
C68A C67A H67A 120.0 . . ?
C66A C67A H67A 120.0 . . ?
C67A C68A C69A 120.0 . . ?
C67A C68A H68A 120.0 . . ?
C69A C68A H68A 120.0 . . ?
C70A C69A C68A 120.0 . . ?
C70A C69A H69A 120.0 . . ?
C68A C69A H69A 120.0 . . ?
C69A C70A C65A 120.0 . . ?
C69A C70A C71A 119.6(6) . . ?
C65A C70A C71A 120.3(6) . . ?
C66B C65B C70B 120.0 . . ?
C66B C65B H65B 120.0 . . ?
C70B C65B H65B 120.0 . . ?
C65B C66B C67B 120.0 . . ?
C65B C66B H66B 120.0 . . ?
C67B C66B H66B 120.0 . . ?
C68B C67B C66B 120.0 . . ?
C68B C67B C71B 119(2) . . ?
C66B C67B C71B 121(2) . . ?
C69B C68B C67B 120.0 . . ?
C69B C68B H68B 120.0 . . ?
C67B C68B H68B 120.0 . . ?
C68B C69B C70B 120.0 . . ?
C68B C69B H69B 120.0 . . ?
C70B C69B H69B 120.0 . . ?
C69B C70B C65B 120.0 . . ?
C69B C70B H70B 120.0 . . ?
C65B C70B H70B 120.0 . . ?
C20 N1 C22 117.2(4) . . ?
C18 N2 C17 116.7(4) . . ?
C52 N5 C54 116.6(4) . . ?
C50 N6 C49 117.1(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.5(7) . . . . ?
C1 C2 C3 C26 179.3(4) . . . . ?
C1 C2 C3 C4 0.7(7) . . . . ?
C26 C3 C4 C23 0.1(7) . . . . ?
C2 C3 C4 C23 178.7(4) . . . . ?
C26 C3 C4 C5 179.1(4) . . . . ?
C2 C3 C4 C5 -2.3(7) . . . . ?
C3 C4 C5 C16 -177.4(4) . . . . ?
C23 C4 C5 C16 1.6(7) . . . . ?
C3 C4 C5 C6 2.7(7) . . . . ?
C23 C4 C5 C6 -178.4(4) . . . . ?
C16 C5 C6 C7 0.0(7) . . . . ?
C4 C5 C6 C7 179.9(4) . . . . ?
C16 C5 C6 C1 178.6(4) . . . . ?
C4 C5 C6 C1 -1.4(7) . . . . ?
C2 C1 C6 C7 178.5(4) . . . . ?
C2 C1 C6 C5 -0.1(7) . . . . ?
C5 C6 C7 C14 2.3(7) . . . . ?
C1 C6 C7 C14 -176.2(4) . . . . ?
C5 C6 C7 C8 -177.7(4) . . . . ?
C1 C6 C7 C8 3.7(7) . . . . ?
C14 C7 C8 C9 -117.0(5) . . . . ?
C6 C7 C8 C9 63.1(6) . . . . ?
C14 C7 C8 C13 62.7(6) . . . . ?
C6 C7 C8 C13 -117.2(5) . . . . ?
C13 C8 C9 C10 -0.4(7) . . . . ?
C7 C8 C9 C10 179.3(5) . . . . ?
C8 C9 C10 C11 0.7(8) . . . . ?
C9 C10 C11 C12 0.0(8) . . . . ?
C10 C11 C12 C13 -1.0(8) . . . . ?
C11 C12 C13 C8 1.2(8) . . . . ?
C9 C8 C13 C12 -0.5(7) . . . . ?
C7 C8 C13 C12 179.8(5) . . . . ?
C6 C7 C14 C15 -2.3(7) . . . . ?
C8 C7 C14 C15 177.8(4) . . . . ?
C7 C14 C15 C16 -0.2(7) . . . . ?
C14 C15 C16 C5 2.5(7) . . . . ?
C14 C15 C16 C17 -178.1(4) . . . . ?
C6 C5 C16 C15 -2.4(7) . . . . ?
C4 C5 C16 C15 177.7(4) . . . . ?
C6 C5 C16 C17 178.2(4) . . . . ?
C4 C5 C16 C17 -1.7(7) . . . . ?
C15 C16 C17 N2 3.4(7) . . . . ?
C5 C16 C17 N2 -177.2(4) . . . . ?
C15 C16 C17 C22 -178.2(4) . . . . ?
C5 C16 C17 C22 1.2(7) . . . . ?
N2 C18 C20 N1 -1.1(7) . . . . ?
C19 C18 C20 N1 178.3(5) . . . . ?
N2 C18 C20 C21 178.5(4) . . . . ?
C19 C18 C20 C21 -2.1(7) . . . . ?
N2 C17 C22 N1 -3.5(7) . . . . ?
C16 C17 C22 N1 178.1(4) . . . . ?
N2 C17 C22 C23 177.9(4) . . . . ?
C16 C17 C22 C23 -0.5(7) . . . . ?
C3 C4 C23 C24 -2.7(7) . . . . ?
C5 C4 C23 C24 178.3(4) . . . . ?
C3 C4 C23 C22 178.1(4) . . . . ?
C5 C4 C23 C22 -0.8(7) . . . . ?
N1 C22 C23 C24 2.5(7) . . . . ?
C17 C22 C23 C24 -178.8(4) . . . . ?
N1 C22 C23 C4 -178.3(4) . . . . ?
C17 C22 C23 C4 0.3(7) . . . . ?
C4 C23 C24 C25 3.2(7) . . . . ?
C22 C23 C24 C25 -177.6(4) . . . . ?
C23 C24 C25 C26 -1.1(7) . . . . ?
C24 C25 C26 C3 -1.5(7) . . . . ?
C24 C25 C26 C27 176.4(4) . . . . ?
C4 C3 C26 C25 1.9(7) . . . . ?
C2 C3 C26 C25 -176.6(4) . . . . ?
C4 C3 C26 C27 -175.9(4) . . . . ?
C2 C3 C26 C27 5.6(7) . . . . ?
C25 C26 C27 C28 -120.2(5) . . . . ?
C3 C26 C27 C28 57.6(6) . . . . ?
C25 C26 C27 C32 55.4(6) . . . . ?
C3 C26 C27 C32 -126.8(5) . . . . ?
C32 C27 C28 C29 0.9(7) . . . . ?
C26 C27 C28 C29 176.6(5) . . . . ?
C27 C28 C29 C30 -1.1(8) . . . . ?
C28 C29 C30 C31 1.0(8) . . . . ?
C29 C30 C31 C32 -0.7(8) . . . . ?
C30 C31 C32 C27 0.6(8) . . . . ?
C28 C27 C32 C31 -0.6(7) . . . . ?
C26 C27 C32 C31 -176.4(4) . . . . ?
C38 C33 C34 C35 -0.3(7) . . . . ?
C33 C34 C35 C58 179.3(5) . . . . ?
C33 C34 C35 C36 0.5(7) . . . . ?
C58 C35 C36 C55 -0.4(7) . . . . ?
C34 C35 C36 C55 178.4(4) . . . . ?
C58 C35 C36 C37 180.0(4) . . . . ?
C34 C35 C36 C37 -1.2(7) . . . . ?
C55 C36 C37 C38 -177.9(4) . . . . ?
C35 C36 C37 C38 1.7(7) . . . . ?
C55 C36 C37 C48 2.7(7) . . . . ?
C35 C36 C37 C48 -177.7(4) . . . . ?
C48 C37 C38 C39 -0.9(7) . . . . ?
C36 C37 C38 C39 179.7(4) . . . . ?
C48 C37 C38 C33 177.9(4) . . . . ?
C36 C37 C38 C33 -1.5(7) . . . . ?
C34 C33 C38 C39 179.6(5) . . . . ?
C34 C33 C38 C37 0.8(7) . . . . ?
C37 C38 C39 C46 3.1(7) . . . . ?
C33 C38 C39 C46 -175.7(4) . . . . ?
C37 C38 C39 C40 -174.1(4) . . . . ?
C33 C38 C39 C40 7.1(7) . . . . ?
C46 C39 C40 C45 57.3(7) . . . . ?
C38 C39 C40 C45 -125.5(5) . . . . ?
C46 C39 C40 C41 -118.4(5) . . . . ?
C38 C39 C40 C41 58.8(7) . . . . ?
C45 C40 C41 C42 -0.1(7) . . . . ?
C39 C40 C41 C42 175.7(4) . . . . ?
C40 C41 C42 C43 0.2(7) . . . . ?
C41 C42 C43 C44 0.6(9) . . . . ?
C42 C43 C44 C45 -1.6(9) . . . . ?
C41 C40 C45 C44 -0.9(8) . . . . ?
C39 C40 C45 C44 -176.7(5) . . . . ?
C43 C44 C45 C40 1.7(9) . . . . ?
C38 C39 C46 C47 -2.6(7) . . . . ?
C40 C39 C46 C47 174.7(4) . . . . ?
C39 C46 C47 C48 -0.3(7) . . . . ?
C46 C47 C48 C37 2.5(7) . . . . ?
C46 C47 C48 C49 -176.7(4) . . . . ?
C38 C37 C48 C47 -1.9(7) . . . . ?
C36 C37 C48 C47 177.5(4) . . . . ?
C38 C37 C48 C49 177.3(4) . . . . ?
C36 C37 C48 C49 -3.3(7) . . . . ?
C47 C48 C49 N6 4.2(7) . . . . ?
C37 C48 C49 N6 -175.0(4) . . . . ?
C47 C48 C49 C54 -177.7(4) . . . . ?
C37 C48 C49 C54 3.1(7) . . . . ?
N6 C50 C52 N5 -2.6(8) . . . . ?
C51 C50 C52 N5 175.3(5) . . . . ?
N6 C50 C52 C53 176.9(5) . . . . ?
C51 C50 C52 C53 -5.2(8) . . . . ?
N6 C49 C54 N5 -4.8(7) . . . . ?
C48 C49 C54 N5 177.2(4) . . . . ?
N6 C49 C54 C55 175.8(4) . . . . ?
C48 C49 C54 C55 -2.2(7) . . . . ?
C35 C36 C55 C56 -1.3(7) . . . . ?
C37 C36 C55 C56 178.4(4) . . . . ?
C35 C36 C55 C54 178.6(4) . . . . ?
C37 C36 C55 C54 -1.8(7) . . . . ?
N5 C54 C55 C56 2.0(7) . . . . ?
C49 C54 C55 C56 -178.6(4) . . . . ?
N5 C54 C55 C36 -177.8(4) . . . . ?
C49 C54 C55 C36 1.5(7) . . . . ?
C36 C55 C56 C57 1.1(7) . . . . ?
C54 C55 C56 C57 -178.7(4) . . . . ?
C55 C56 C57 C58 0.8(7) . . . . ?
C56 C57 C58 C35 -2.5(7) . . . . ?
C56 C57 C58 C59 178.0(4) . . . . ?
C36 C35 C58 C57 2.3(7) . . . . ?
C34 C35 C58 C57 -176.5(4) . . . . ?
C36 C35 C58 C59 -178.2(4) . . . . ?
C34 C35 C58 C59 3.1(7) . . . . ?
C57 C58 C59 C64 -122.1(5) . . . . ?
C35 C58 C59 C64 58.3(7) . . . . ?
C57 C58 C59 C60 54.3(6) . . . . ?
C35 C58 C59 C60 -125.3(5) . . . . ?
C64 C59 C60 C61 1.9(8) . . . . ?
C58 C59 C60 C61 -174.5(4) . . . . ?
C59 C60 C61 C62 -0.4(8) . . . . ?
C60 C61 C62 C63 -1.6(8) . . . . ?
C61 C62 C63 C64 2.0(8) . . . . ?
C60 C59 C64 C63 -1.4(8) . . . . ?
C58 C59 C64 C63 174.9(5) . . . . ?
C62 C63 C64 C59 -0.5(8) . . . . ?
C70A C65A C66A C67A 0.0 . . . . ?
C65A C66A C67A C68A 0.0 . . . . ?
C66A C67A C68A C69A 0.0 . . . . ?
C67A C68A C69A C70A 0.0 . . . . ?
C68A C69A C70A C65A 0.0 . . . . ?
C68A C69A C70A C71A 177.0(6) . . . . ?
C66A C65A C70A C69A 0.0 . . . . ?
C66A C65A C70A C71A -177.0(6) . . . . ?
C70B C65B C66B C67B 0.0 . . . . ?
C65B C66B C67B C68B 0.0 . . . . ?
C65B C66B C67B C71B 173(3) . . . . ?
C66B C67B C68B C69B 0.0 . . . . ?
C71B C67B C68B C69B -173(3) . . . . ?
C67B C68B C69B C70B 0.0 . . . . ?
C68B C69B C70B C65B 0.0 . . . . ?
C66B C65B C70B C69B 0.0 . . . . ?
C18 C20 N1 C22 -0.3(7) . . . . ?
C21 C20 N1 C22 -179.9(4) . . . . ?
C17 C22 N1 C20 2.5(7) . . . . ?
C23 C22 N1 C20 -178.8(4) . . . . ?
C20 C18 N2 C17 0.2(7) . . . . ?
C19 C18 N2 C17 -179.3(4) . . . . ?
C22 C17 N2 C18 2.1(7) . . . . ?
C16 C17 N2 C18 -179.5(4) . . . . ?
C50 C52 N5 C54 0.6(7) . . . . ?
C53 C52 N5 C54 -179.0(4) . . . . ?
C49 C54 N5 C52 3.0(7) . . . . ?
C55 C54 N5 C52 -177.6(4) . . . . ?
C52 C50 N6 C49 0.9(7) . . . . ?
C51 C50 N6 C49 -177.2(4) . . . . ?
C54 C49 N6 C50 2.7(7) . . . . ?
C48 C49 N6 C50 -179.3(4) . . . . ?

_refine_diff_density_max         0.233
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.052



####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1959738'
loop_
_audit_author_name
_audit_author_address
'Denis Spasyuk'
;Canadian Light Source Inc
Canada
;
_audit_update_record             
;
2019-10-16 deposited with the CCDC.	2019-11-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C68 H40 N4'
_chemical_formula_sum            'C68 H40 N4'
_chemical_formula_weight         913.04

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_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+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   23.746(5)
_cell_length_b                   13.717(3)
_cell_length_c                   6.8210(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2221.8(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    4643
_cell_measurement_theta_min      3.25
_cell_measurement_theta_max      29.50

_exptl_crystal_description       prism
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.015
_exptl_crystal_size_min          0.012
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1956
_exptl_absorpt_correction_T_max  0.2647
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.7749
_diffrn_radiation_type           synchrotron
_diffrn_source                   synchrotron
_diffrn_measurement_device_type  'Rayonix MX300HE CCD area detector'
_diffrn_measurement_method       'κ and ω scans'
_diffrn_detector_area_resol_mean 8.3
_diffrn_reflns_number            23076
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_av_R_equivalents  0.1016
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.238
_diffrn_reflns_theta_max         26.752
_diffrn_reflns_theta_full        26.752
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1813
_reflns_number_gt                1396
_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       'MxDC, (Fodje, 2012)'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_reduction        'XDS (Kabsch, 2010)'
_computing_structure_solution    'SHELXL2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ShelXle (Hubschle, 2011)'
_computing_publication_material  'Linxtl  6.0.1'
_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1267P)²+12.4879P] 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         1813
_refine_ls_number_parameters     218
_refine_ls_number_restraints     575
_refine_ls_R_factor_all          0.1452
_refine_ls_R_factor_gt           0.1245
_refine_ls_wR_factor_ref         0.3523
_refine_ls_wR_factor_gt          0.3404
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_restrained_S_all      367.938
_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
C1 C 0.4401(2) 0.6411(4) 0.7205(8) 0.0306(13) Uani 1 1 d . . . . .
C2 C 0.3812(2) 0.6404(4) 0.6859(9) 0.0333(13) Uani 1 1 d D . . . .
C3 C 0.3542(3) 0.5519(5) 0.6546(8) 0.0372(14) Uani 1 1 d . . . . .
H3 H 0.315398 0.551592 0.621148 0.045 Uiso 1 1 calc R U . . .
C4 C 0.3826(3) 0.4642(4) 0.6709(9) 0.0400(15) Uani 1 1 d . . . . .
H4 H 0.362700 0.404746 0.653193 0.048 Uiso 1 1 calc R U . . .
C5 C 0.4400(3) 0.4619(4) 0.7130(9) 0.0379(15) Uani 1 1 d . . . . .
C6 C 0.4695(3) 0.5504(4) 0.7327(8) 0.0313(14) Uani 1 1 d . . . . .
C7 C 0.4692(2) 0.3683(4) 0.7359(9) 0.0400(16) Uani 1 1 d D . . . .
C11A C 0.3481(8) 0.7272(11) 0.665(3) 0.037(2) Uani 0.386(17) 1 d DG U P A 1
C12A C 0.3477(8) 0.7954(13) 0.815(2) 0.037(2) Uani 0.386(17) 1 d G U P A 1
H12A H 0.370134 0.785313 0.928668 0.044 Uiso 0.386(17) 1 calc R U P A 1
C13A C 0.3144(7) 0.8784(10) 0.800(2) 0.041(2) Uani 0.386(17) 1 d G U P A 1
H13A H 0.314074 0.925029 0.903060 0.049 Uiso 0.386(17) 1 calc R U P A 1
C14A C 0.2815(6) 0.8932(9) 0.634(3) 0.041(2) Uani 0.386(17) 1 d G U P A 1
H14A H 0.258699 0.949928 0.623745 0.049 Uiso 0.386(17) 1 calc R U P A 1
C15A C 0.2819(6) 0.8250(11) 0.483(2) 0.042(2) Uani 0.386(17) 1 d G U P A 1
H15A H 0.259382 0.835110 0.370035 0.051 Uiso 0.386(17) 1 calc R U P A 1
C16A C 0.3152(8) 0.7420(11) 0.499(2) 0.040(2) Uani 0.386(17) 1 d G U P A 1
H16A H 0.315442 0.695393 0.395639 0.048 Uiso 0.386(17) 1 calc R U P A 1
C11B C 0.3467(5) 0.7370(7) 0.6972(16) 0.0349(18) Uani 0.614(17) 1 d DG U P A 2
C12B C 0.3508(5) 0.7952(8) 0.8634(15) 0.0368(18) Uani 0.614(17) 1 d G U P A 2
H12B H 0.375035 0.776701 0.967713 0.044 Uiso 0.614(17) 1 calc R U P A 2
C13B C 0.3193(4) 0.8804(6) 0.8771(16) 0.0399(19) Uani 0.614(17) 1 d G U P A 2
H13B H 0.322117 0.920154 0.990672 0.048 Uiso 0.614(17) 1 calc R U P A 2
C14B C 0.2838(3) 0.9074(5) 0.7245(19) 0.042(2) Uani 0.614(17) 1 d G U P A 2
H14B H 0.262332 0.965661 0.733776 0.050 Uiso 0.614(17) 1 calc R U P A 2
C15B C 0.2797(4) 0.8492(7) 0.5582(16) 0.044(2) Uani 0.614(17) 1 d G U P A 2
H15B H 0.255465 0.867715 0.453918 0.052 Uiso 0.614(17) 1 calc R U P A 2
C16B C 0.3112(5) 0.7640(7) 0.5446(14) 0.043(2) Uani 0.614(17) 1 d G U P A 2
H16B H 0.308382 0.724261 0.430956 0.051 Uiso 0.614(17) 1 calc R U P A 2
C23 C 0.4718(2) 0.7301(4) 0.7358(8) 0.0285(13) Uani 1 1 d . . . . .
H23 H 0.452575 0.790672 0.725547 0.034 Uiso 1 1 calc R U . . .
N1 N 0.4282(8) 0.2902(11) 0.727(5) 0.035(4) Uani 0.386(17) 1 d . U P A -1
N2 N -3.9453(5) -2.7836(8) 1.234(2) 0.027(3) Uani 0.614(17) 1 d D U P A -1
C17 C 0.4606(3) 0.2016(4) 0.746(2) 0.029(2) Uani 0.5 1 d G U P A -1
C18 C 0.4301(2) 0.1152(5) 0.7445(16) 0.032(2) Uani 0.5 1 d G U P A -1
H18 H 0.390075 0.116934 0.741198 0.039 Uiso 0.5 1 calc R U P A -1
C19 C 0.4580(3) 0.0262(4) 0.7479(19) 0.038(3) Uani 0.5 1 d G U P A -1
H19 H 0.437157 -0.032900 0.746961 0.045 Uiso 0.5 1 calc R U P A -1
C20 C 0.5165(3) 0.0236(4) 0.7527(19) 0.035(3) Uani 0.5 1 d G U P A -1
H20 H 0.535640 -0.037195 0.755049 0.042 Uiso 0.5 1 calc R U P A -1
C21 C 0.5471(2) 0.1101(5) 0.7541(16) 0.032(2) Uani 0.5 1 d G U P A -1
H21 H 0.587044 0.108343 0.757376 0.038 Uiso 0.5 1 calc R U P A -1
C22 C 0.5191(3) 0.1991(4) 0.751(2) 0.030(3) Uani 0.5 1 d G 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
C1 C2 1.420(8) . ?
C1 C6 1.428(8) . ?
C1 C23 1.438(8) . ?
C2 C3 1.389(8) . ?
C2 C11A 1.434(10) . ?
C2 C11B 1.559(8) . ?
C3 C4 1.384(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(10) . ?
C4 H4 0.9500 . ?
C5 C6 1.408(8) . ?
C5 C7 1.468(9) . ?
C6 C6 1.467(12) 3_656 ?
C7 N1 1.448(16) . ?
C7 C7 1.477(12) 3_656 ?
C11A C12A 1.3900 . ?
C11A C16A 1.3900 . ?
C12A C13A 1.3900 . ?
C12A H12A 0.9500 . ?
C13A C14A 1.3900 . ?
C13A H13A 0.9500 . ?
C14A C15A 1.3900 . ?
C14A H14A 0.9500 . ?
C15A C16A 1.3900 . ?
C15A H15A 0.9500 . ?
C16A H16A 0.9500 . ?
C11B C12B 1.3900 . ?
C11B C16B 1.3900 . ?
C12B C13B 1.3900 . ?
C12B H12B 0.9500 . ?
C13B C14B 1.3900 . ?
C13B H13B 0.9500 . ?
C14B C15B 1.3900 . ?
C14B H14B 0.9500 . ?
C15B C16B 1.3900 . ?
C15B H15B 0.9500 . ?
C16B H16B 0.9500 . ?
C23 C23 1.354(12) 3_656 ?
C23 H23 0.9500 . ?
N1 C17 1.443(16) . ?
C17 C18 1.3900 . ?
C17 C22 1.3900 . ?
C18 C19 1.3900 . ?
C18 H18 0.9500 . ?
C19 C20 1.3900 . ?
C19 H19 0.9500 . ?
C20 C21 1.3900 . ?
C20 H20 0.9500 . ?
C21 C22 1.3900 . ?
C21 H21 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 C1 C6 119.0(5) . . ?
C2 C1 C23 122.2(5) . . ?
C6 C1 C23 118.7(5) . . ?
C3 C2 C1 119.0(5) . . ?
C3 C2 C11A 117.2(10) . . ?
C1 C2 C11A 123.5(10) . . ?
C3 C2 C11B 120.5(7) . . ?
C1 C2 C11B 120.3(7) . . ?
C4 C3 C2 121.6(6) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 120.8(6) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 119.2(6) . . ?
C4 C5 C7 120.2(5) . . ?
C6 C5 C7 120.6(6) . . ?
C5 C6 C1 120.1(5) . . ?
C5 C6 C6 120.5(4) . 3_656 ?
C1 C6 C6 119.4(3) . 3_656 ?
N1 C7 C5 109.0(8) . . ?
N1 C7 C7 132.2(7) . 3_656 ?
C5 C7 C7 118.8(3) . 3_656 ?
C12A C11A C16A 120.0 . . ?
C12A C11A C2 119.2(10) . . ?
C16A C11A C2 120.8(10) . . ?
C11A C12A C13A 120.0 . . ?
C11A C12A H12A 120.0 . . ?
C13A C12A H12A 120.0 . . ?
C12A C13A C14A 120.0 . . ?
C12A C13A H13A 120.0 . . ?
C14A C13A H13A 120.0 . . ?
C15A C14A C13A 120.0 . . ?
C15A C14A H14A 120.0 . . ?
C13A C14A H14A 120.0 . . ?
C16A C15A C14A 120.0 . . ?
C16A C15A H15A 120.0 . . ?
C14A C15A H15A 120.0 . . ?
C15A C16A C11A 120.0 . . ?
C15A C16A H16A 120.0 . . ?
C11A C16A H16A 120.0 . . ?
C12B C11B C16B 120.0 . . ?
C12B C11B C2 119.4(6) . . ?
C16B C11B C2 120.6(6) . . ?
C13B C12B C11B 120.0 . . ?
C13B C12B H12B 120.0 . . ?
C11B C12B H12B 120.0 . . ?
C14B C13B C12B 120.0 . . ?
C14B C13B H13B 120.0 . . ?
C12B C13B H13B 120.0 . . ?
C13B C14B C15B 120.0 . . ?
C13B C14B H14B 120.0 . . ?
C15B C14B H14B 120.0 . . ?
C16B C15B C14B 120.0 . . ?
C16B C15B H15B 120.0 . . ?
C14B C15B H15B 120.0 . . ?
C15B C16B C11B 120.0 . . ?
C15B C16B H16B 120.0 . . ?
C11B C16B H16B 120.0 . . ?
C23 C23 C1 121.8(3) 3_656 . ?
C23 C23 H23 119.1 3_656 . ?
C1 C23 H23 119.1 . . ?
C17 N1 C7 105.2(12) . . ?
C18 C17 C22 120.0 . . ?
C18 C17 N1 116.1(9) . . ?
C22 C17 N1 123.7(9) . . ?
C17 C18 C19 120.0 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C20 120.0 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C21 C20 C19 120.0 . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 120.0 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C17 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
C6 C1 C2 C3 -3.4(8) . . . . ?
C23 C1 C2 C3 174.0(5) . . . . ?
C6 C1 C2 C11A -177.8(10) . . . . ?
C23 C1 C2 C11A -0.5(12) . . . . ?
C6 C1 C2 C11B 172.5(6) . . . . ?
C23 C1 C2 C11B -10.1(9) . . . . ?
C1 C2 C3 C4 4.9(9) . . . . ?
C11A C2 C3 C4 179.8(10) . . . . ?
C11B C2 C3 C4 -170.9(7) . . . . ?
C2 C3 C4 C5 -2.2(9) . . . . ?
C3 C4 C5 C6 -2.1(9) . . . . ?
C3 C4 C5 C7 178.1(5) . . . . ?
C4 C5 C6 C1 3.5(8) . . . . ?
C7 C5 C6 C1 -176.7(5) . . . . ?
C4 C5 C6 C6 -177.0(6) . . . 3_656 ?
C7 C5 C6 C6 2.9(10) . . . 3_656 ?
C2 C1 C6 C5 -0.8(8) . . . . ?
C23 C1 C6 C5 -178.3(5) . . . . ?
C2 C1 C6 C6 179.7(6) . . . 3_656 ?
C23 C1 C6 C6 2.2(9) . . . 3_656 ?
C4 C5 C7 N1 -5.4(16) . . . . ?
C6 C5 C7 N1 174.7(14) . . . . ?
C4 C5 C7 C7 175.0(7) . . . 3_656 ?
C6 C5 C7 C7 -4.8(10) . . . 3_656 ?
C3 C2 C11A C12A 127.8(9) . . . . ?
C1 C2 C11A C12A -57.6(15) . . . . ?
C3 C2 C11A C16A -50.0(15) . . . . ?
C1 C2 C11A C16A 124.5(10) . . . . ?
C16A C11A C12A C13A 0.0 . . . . ?
C2 C11A C12A C13A -177.9(18) . . . . ?
C11A C12A C13A C14A 0.0 . . . . ?
C12A C13A C14A C15A 0.0 . . . . ?
C13A C14A C15A C16A 0.0 . . . . ?
C14A C15A C16A C11A 0.0 . . . . ?
C12A C11A C16A C15A 0.0 . . . . ?
C2 C11A C16A C15A 177.8(18) . . . . ?
C3 C2 C11B C12B 123.1(7) . . . . ?
C1 C2 C11B C12B -52.7(9) . . . . ?
C3 C2 C11B C16B -55.5(10) . . . . ?
C1 C2 C11B C16B 128.7(7) . . . . ?
C16B C11B C12B C13B 0.0 . . . . ?
C2 C11B C12B C13B -178.6(10) . . . . ?
C11B C12B C13B C14B 0.0 . . . . ?
C12B C13B C14B C15B 0.0 . . . . ?
C13B C14B C15B C16B 0.0 . . . . ?
C14B C15B C16B C11B 0.0 . . . . ?
C12B C11B C16B C15B 0.0 . . . . ?
C2 C11B C16B C15B 178.6(11) . . . . ?
C2 C1 C23 C23 -178.4(7) . . . 3_656 ?
C6 C1 C23 C23 -1.1(10) . . . 3_656 ?
C5 C7 N1 C17 178.8(14) . . . . ?
C7 C7 N1 C17 -2(3) 3_656 . . . ?
C7 N1 C17 C18 179.0(13) . . . . ?
C7 N1 C17 C22 -6(3) . . . . ?
C22 C17 C18 C19 0.0 . . . . ?
N1 C17 C18 C19 175.3(17) . . . . ?
C17 C18 C19 C20 0.0 . . . . ?
C18 C19 C20 C21 0.0 . . . . ?
C19 C20 C21 C22 0.0 . . . . ?
C20 C21 C22 C17 0.0 . . . . ?
C18 C17 C22 C21 0.0 . . . . ?
N1 C17 C22 C21 -174.9(19) . . . . ?

_refine_diff_density_max         0.410
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.094



####################################################################### 
# 
# 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_dth6-96a
_database_code_depnum_ccdc_archive 'CCDC 1959739'
loop_
_audit_author_name
_audit_author_address
'Denis Spasyuk'
;Canadian Light Source Inc
Canada
;
_audit_update_record             
;
2019-10-16 deposited with the CCDC.	2019-11-29 downloaded from the CCDC.
;
_audit_creation_date             2019-04-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C38 H30 N4'
_chemical_formula_sum            'C38 H30 N4'
_chemical_formula_weight         542.66
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   9.3641(9)
_cell_length_b                   17.2562(17)
_cell_length_c                   17.3647(16)
_cell_angle_alpha                90
_cell_angle_beta                 101.383(3)
_cell_angle_gamma                90
_cell_volume                     2750.7(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9893
_cell_measurement_temperature    173
_cell_measurement_theta_max      30.032
_cell_measurement_theta_min      3.240
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0673 before and 0.0574 after correction. The Ratio of minimum to maximum transmission is 0.8759. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.26
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            39971
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.750
_diffrn_reflns_theta_max         25.750
_diffrn_reflns_theta_min         1.680
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3594
_reflns_number_total             5233
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 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         0.278
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         5233
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0683
_refine_ls_restrained_S_all      1.103
_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)+(0.0484P)²+5.4314P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1742
_refine_ls_wR_factor_ref         0.1919
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C12(H12), C14(H14), C15(H15),
 C20(H20), C21(H21), C23(H23), C24(H24), C28(H28), C29(H29), C31(H31), C32(H32),
  C00C(H00C), C00N(H00N)
2.b Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C33(H33A,H33B,H33C), C34(H34A,H34B,
 H34C)
;
_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 0.7747(3) 0.83240(15) 0.70565(15) 0.0277(6) Uani 1 1 d . . . . .
N2 N 0.7077(3) 0.82934(15) 0.53956(15) 0.0263(6) Uani 1 1 d . . . . .
N3 N 0.7816(3) 0.28252(16) 0.98199(16) 0.0320(6) Uani 1 1 d . . . . .
N4 N 0.7183(3) 0.28146(16) 0.26481(16) 0.0314(6) Uani 1 1 d . . . . .
C1 C 0.7538(3) 0.89944(19) 0.66303(18) 0.0280(7) Uani 1 1 d . . . . .
C2 C 0.7684(4) 0.9715(2) 0.7021(2) 0.0384(8) Uani 1 1 d . . . . .
H2 H 0.797630 0.973627 0.757688 0.046 Uiso 1 1 calc R . . . .
C3 C 0.7402(4) 1.0383(2) 0.6596(2) 0.0415(9) Uani 1 1 d . . . . .
H3 H 0.750190 1.086883 0.685876 0.050 Uiso 1 1 calc R . . . .
C4 C 0.6967(4) 1.0362(2) 0.5775(2) 0.0390(9) Uani 1 1 d . . . . .
H4 H 0.674618 1.083277 0.549332 0.047 Uiso 1 1 calc R . . . .
C5 C 0.6856(4) 0.96789(19) 0.5376(2) 0.0320(7) Uani 1 1 d . . . . .
H5 H 0.657743 0.967559 0.481918 0.038 Uiso 1 1 calc R . . . .
C6 C 0.7158(3) 0.89723(18) 0.57933(18) 0.0265(7) Uani 1 1 d . . . . .
C007 C 0.7239(3) 0.54779(18) 0.46014(17) 0.0257(7) Uani 1 1 d . . . . .
C7 C 0.7620(3) 0.76632(18) 0.66563(17) 0.0224(6) Uani 1 1 d . . . . .
C8 C 0.7774(3) 0.69319(18) 0.70944(17) 0.0235(6) Uani 1 1 d . . . . .
C9 C 0.7958(3) 0.69292(18) 0.79064(17) 0.0261(7) Uani 1 1 d . . . . .
H9 H 0.804451 0.740659 0.818422 0.031 Uiso 1 1 calc R . . . .
C10 C 0.7940(3) 0.55238(18) 0.79348(17) 0.0256(7) Uani 1 1 d . . . . .
C11 C 0.7851(3) 0.55127(18) 0.71106(17) 0.0235(6) Uani 1 1 d . . . . .
C12 C 0.7862(3) 0.48025(19) 0.66853(18) 0.0278(7) Uani 1 1 d . . . . .
H12 H 0.798636 0.432668 0.696585 0.033 Uiso 1 1 calc R . . . .
C13 C 0.7493(3) 0.54912(18) 0.54345(17) 0.0236(7) Uani 1 1 d . . . . .
C14 C 0.6966(4) 0.61729(19) 0.41965(18) 0.0291(7) Uani 1 1 d . . . . .
H14 H 0.676192 0.616679 0.363847 0.035 Uiso 1 1 calc R . . . .
C15 C 0.6983(3) 0.68782(19) 0.45865(18) 0.0291(7) Uani 1 1 d . . . . .
H15 H 0.679816 0.734354 0.429121 0.035 Uiso 1 1 calc R . . . .
C16 C 0.7268(3) 0.69112(18) 0.54036(17) 0.0234(6) Uani 1 1 d . . . . .
C17 C 0.7326(3) 0.76483(18) 0.58162(17) 0.0222(6) Uani 1 1 d . . . . .
C18 C 0.7503(3) 0.62109(18) 0.58371(17) 0.0218(6) Uani 1 1 d . . . . .
C19 C 0.7922(3) 0.47998(18) 0.83993(17) 0.0254(7) Uani 1 1 d . . . . .
C20 C 0.9127(3) 0.45761(19) 0.89615(18) 0.0284(7) Uani 1 1 d . . . . .
H20 H 0.998995 0.487892 0.902849 0.034 Uiso 1 1 calc R . . . .
C21 C 0.9105(3) 0.39264(19) 0.94251(18) 0.0282(7) Uani 1 1 d . . . . .
H21 H 0.995398 0.378703 0.979566 0.034 Uiso 1 1 calc R . . . .
C22 C 0.7847(3) 0.34706(18) 0.93564(17) 0.0254(7) Uani 1 1 d . . . . .
C23 C 0.6621(3) 0.37013(18) 0.87969(18) 0.0283(7) Uani 1 1 d . . . . .
H23 H 0.574382 0.341182 0.874010 0.034 Uiso 1 1 calc R . . . .
C24 C 0.6678(3) 0.43443(19) 0.83288(18) 0.0294(7) Uani 1 1 d . . . . .
H24 H 0.584156 0.447911 0.794707 0.035 Uiso 1 1 calc R . . . .
C25 C 0.9063(4) 0.2612(2) 1.0400(2) 0.0434(9) Uani 1 1 d . . . . .
H25A H 0.991579 0.256923 1.015401 0.065 Uiso 1 1 calc GR . . . .
H25B H 0.888416 0.211151 1.063160 0.065 Uiso 1 1 calc GR . . . .
H25C H 0.924322 0.300758 1.081262 0.065 Uiso 1 1 calc GR . . . .
C26 C 0.6444(4) 0.24503(19) 0.9855(2) 0.0337(8) Uani 1 1 d . . . . .
H26A H 0.579287 0.282301 1.003647 0.051 Uiso 1 1 calc GR . . . .
H26B H 0.662108 0.201281 1.022162 0.051 Uiso 1 1 calc GR . . . .
H26C H 0.599148 0.226166 0.933156 0.051 Uiso 1 1 calc GR . . . .
C27 C 0.7222(3) 0.47475(18) 0.41424(17) 0.0249(7) Uani 1 1 d . . . . .
C28 C 0.8460(3) 0.42951(19) 0.41628(18) 0.0296(7) Uani 1 1 d . . . . .
H28 H 0.933204 0.442807 0.451895 0.036 Uiso 1 1 calc R . . . .
C29 C 0.8458(3) 0.36601(19) 0.36816(18) 0.0285(7) Uani 1 1 d . . . . .
H29 H 0.932772 0.336911 0.370876 0.034 Uiso 1 1 calc R . . . .
C30 C 0.7190(3) 0.34353(17) 0.31510(17) 0.0239(7) Uani 1 1 d . . . . .
C31 C 0.5933(3) 0.38825(18) 0.31398(17) 0.0258(7) Uani 1 1 d . . . . .
H31 H 0.504951 0.374267 0.279718 0.031 Uiso 1 1 calc R . . . .
C32 C 0.5964(3) 0.45234(18) 0.36204(17) 0.0255(7) Uani 1 1 d . . . . .
H32 H 0.510013 0.481964 0.359376 0.031 Uiso 1 1 calc R . . . .
C33 C 0.8517(4) 0.2418(2) 0.2604(2) 0.0364(8) Uani 1 1 d . . . . .
H33A H 0.923187 0.279134 0.248573 0.055 Uiso 1 1 calc GR . . . .
H33B H 0.832607 0.202508 0.218883 0.055 Uiso 1 1 calc GR . . . .
H33C H 0.890209 0.216613 0.310860 0.055 Uiso 1 1 calc GR . . . .
C34 C 0.5859(4) 0.2582(2) 0.2127(2) 0.0387(9) Uani 1 1 d . . . . .
H34A H 0.509028 0.250569 0.242944 0.058 Uiso 1 1 calc GR . . . .
H34B H 0.602529 0.209588 0.186625 0.058 Uiso 1 1 calc GR . . . .
H34C H 0.556065 0.298556 0.173110 0.058 Uiso 1 1 calc GR . . . .
C00C C 0.8017(3) 0.62373(19) 0.83173(18) 0.0287(7) Uani 1 1 d . . . . .
H00C H 0.811283 0.624965 0.887206 0.034 Uiso 1 1 calc R . . . .
C00N C 0.7700(3) 0.47925(18) 0.58925(18) 0.0266(7) Uani 1 1 d . . . . .
H00N H 0.772370 0.430982 0.563228 0.032 Uiso 1 1 calc R . . . .
C00O C 0.7722(3) 0.62235(18) 0.66844(17) 0.0223(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.366(4) . ?
N1 C7 1.328(4) . ?
N2 C6 1.354(4) . ?
N2 C17 1.326(4) . ?
N3 C22 1.378(4) . ?
N3 C25 1.432(4) . ?
N3 C26 1.451(4) . ?
N4 C30 1.381(4) . ?
N4 C33 1.440(4) . ?
N4 C34 1.440(4) . ?
C1 C2 1.411(4) . ?
C1 C6 1.427(4) . ?
C2 C3 1.367(5) . ?
C3 C4 1.403(5) . ?
C4 C5 1.361(5) . ?
C5 C6 1.418(4) . ?
C007 C13 1.419(4) . ?
C007 C14 1.388(4) . ?
C007 C27 1.490(4) . ?
C7 C8 1.466(4) . ?
C7 C17 1.430(4) . ?
C8 C9 1.386(4) . ?
C8 C00O 1.411(4) . ?
C9 C00C 1.386(4) . ?
C10 C11 1.417(4) . ?
C10 C19 1.489(4) . ?
C10 C00C 1.394(4) . ?
C11 C12 1.432(4) . ?
C11 C00O 1.425(4) . ?
C12 C00N 1.355(4) . ?
C13 C18 1.424(4) . ?
C13 C00N 1.436(4) . ?
C14 C15 1.391(4) . ?
C15 C16 1.392(4) . ?
C16 C17 1.456(4) . ?
C16 C18 1.418(4) . ?
C18 C00O 1.445(4) . ?
C19 C20 1.393(4) . ?
C19 C24 1.391(4) . ?
C20 C21 1.383(4) . ?
C21 C22 1.401(4) . ?
C22 C23 1.407(4) . ?
C23 C24 1.383(4) . ?
C27 C28 1.392(4) . ?
C27 C32 1.392(4) . ?
C28 C29 1.378(4) . ?
C29 C30 1.406(4) . ?
C30 C31 1.404(4) . ?
C31 C32 1.382(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
C7 N1 C1 117.1(3) . . ?
C17 N2 C6 117.3(3) . . ?
C22 N3 C25 120.7(3) . . ?
C22 N3 C26 120.4(3) . . ?
C25 N3 C26 117.5(3) . . ?
C30 N4 C33 120.5(3) . . ?
C30 N4 C34 120.6(3) . . ?
C33 N4 C34 118.8(3) . . ?
N1 C1 C2 119.7(3) . . ?
N1 C1 C6 120.6(3) . . ?
C2 C1 C6 119.6(3) . . ?
C3 C2 C1 119.6(3) . . ?
C2 C3 C4 120.9(3) . . ?
C5 C4 C3 121.2(3) . . ?
C4 C5 C6 119.8(3) . . ?
N2 C6 C1 121.3(3) . . ?
N2 C6 C5 119.8(3) . . ?
C5 C6 C1 118.8(3) . . ?
C13 C007 C27 122.8(3) . . ?
C14 C007 C13 118.6(3) . . ?
C14 C007 C27 118.6(3) . . ?
N1 C7 C8 118.6(3) . . ?
N1 C7 C17 121.9(3) . . ?
C17 C7 C8 119.6(3) . . ?
C9 C8 C7 120.7(3) . . ?
C9 C8 C00O 119.7(3) . . ?
C00O C8 C7 119.6(3) . . ?
C8 C9 C00C 120.7(3) . . ?
C11 C10 C19 122.1(3) . . ?
C00C C10 C11 118.7(3) . . ?
C00C C10 C19 119.2(3) . . ?
C10 C11 C12 121.8(3) . . ?
C10 C11 C00O 119.7(3) . . ?
C00O C11 C12 118.5(3) . . ?
C00N C12 C11 121.6(3) . . ?
C007 C13 C18 119.9(3) . . ?
C007 C13 C00N 121.9(3) . . ?
C18 C13 C00N 118.2(3) . . ?
C007 C14 C15 121.7(3) . . ?
C14 C15 C16 120.9(3) . . ?
C15 C16 C17 121.2(3) . . ?
C15 C16 C18 119.0(3) . . ?
C18 C16 C17 119.8(3) . . ?
N2 C17 C7 121.6(3) . . ?
N2 C17 C16 118.5(3) . . ?
C7 C17 C16 119.9(3) . . ?
C13 C18 C00O 119.9(3) . . ?
C16 C18 C13 119.8(3) . . ?
C16 C18 C00O 120.3(3) . . ?
C20 C19 C10 121.2(3) . . ?
C24 C19 C10 121.7(3) . . ?
C24 C19 C20 117.0(3) . . ?
C21 C20 C19 122.0(3) . . ?
C20 C21 C22 121.0(3) . . ?
N3 C22 C21 121.2(3) . . ?
N3 C22 C23 121.6(3) . . ?
C21 C22 C23 117.2(3) . . ?
C24 C23 C22 120.8(3) . . ?
C23 C24 C19 122.1(3) . . ?
C28 C27 C007 122.7(3) . . ?
C28 C27 C32 117.0(3) . . ?
C32 C27 C007 120.1(3) . . ?
C29 C28 C27 121.9(3) . . ?
C28 C29 C30 121.1(3) . . ?
N4 C30 C29 121.7(3) . . ?
N4 C30 C31 121.2(3) . . ?
C31 C30 C29 117.0(3) . . ?
C32 C31 C30 120.9(3) . . ?
C31 C32 C27 122.0(3) . . ?
C9 C00C C10 121.5(3) . . ?
C12 C00N C13 121.9(3) . . ?
C8 C00O C11 119.5(3) . . ?
C8 C00O C18 120.7(3) . . ?
C11 C00O C18 119.8(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
