# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2020

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

data_ic19276
_database_code_depnum_ccdc_archive 'CCDC 1969129'
loop_
_audit_author_name
_audit_author_address
'Man-Kit Leung'
;National Taiwan University
Taiwan
;
_audit_update_record             
;
2019-11-30 deposited with the CCDC.	2020-01-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H19 N3'
_chemical_formula_weight         433.49

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

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

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

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

_cell_length_a                   15.6048(7)
_cell_length_b                   9.9970(3)
_cell_length_c                   13.6929(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.901(4)
_cell_angle_gamma                90
_cell_volume                     2020.93(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5280
_cell_measurement_theta_min      3.4350
_cell_measurement_theta_max      28.8700

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91973
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2496
_diffrn_reflns_number            13710
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.997
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4488
_reflns_number_gt                3468
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0487P)²+2.4546P] 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         4488
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0607
_refine_ls_wR_factor_ref         0.1673
_refine_ls_wR_factor_gt          0.1558
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_restrained_S_all      1.173
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.17932(14) 0.1703(2) 0.59050(15) 0.0203(4) Uani 1 1 d . . . . .
N2 N 0.35261(14) 0.3152(2) 0.60591(15) 0.0207(4) Uani 1 1 d . . . . .
N3 N 0.36756(13) 0.5411(2) 0.60957(15) 0.0191(4) Uani 1 1 d . . . . .
C1 C 0.13321(16) 0.1002(2) 0.64633(18) 0.0193(5) Uani 1 1 d . . . . .
C2 C 0.11703(17) 0.1380(3) 0.7366(2) 0.0241(5) Uani 1 1 d . . . . .
H2A H 0.134793 0.223438 0.766640 0.029 Uiso 1 1 calc R U . . .
C3 C 0.07401(17) 0.0463(3) 0.7811(2) 0.0266(6) Uani 1 1 d . . . . .
H3A H 0.064090 0.068469 0.844081 0.032 Uiso 1 1 calc R U . . .
C4 C 0.04492(17) -0.0780(3) 0.7353(2) 0.0270(6) Uani 1 1 d . . . . .
H4A H 0.014015 -0.137823 0.766279 0.032 Uiso 1 1 calc R U . . .
C5 C 0.06091(17) -0.1141(3) 0.6455(2) 0.0247(5) Uani 1 1 d . . . . .
H5A H 0.040857 -0.198337 0.614386 0.030 Uiso 1 1 calc R U . . .
C6 C 0.10664(16) -0.0262(2) 0.60053(19) 0.0204(5) Uani 1 1 d . . . . .
C7 C 0.13739(16) -0.0327(2) 0.51162(18) 0.0207(5) Uani 1 1 d . . . . .
C8 C 0.12882(17) -0.1277(3) 0.43422(19) 0.0234(5) Uani 1 1 d . . . . .
H8A H 0.098330 -0.209833 0.434613 0.028 Uiso 1 1 calc R U . . .
C9 C 0.16550(17) -0.1001(3) 0.35692(19) 0.0241(5) Uani 1 1 d . . . . .
H9A H 0.159675 -0.163574 0.303529 0.029 Uiso 1 1 calc R U . . .
C10 C 0.21101(17) 0.0203(3) 0.35663(19) 0.0249(6) Uani 1 1 d . . . . .
H10A H 0.236305 0.036345 0.303265 0.030 Uiso 1 1 calc R U . . .
C11 C 0.22023(17) 0.1163(3) 0.43160(18) 0.0223(5) Uani 1 1 d . . . . .
H11A H 0.251360 0.197796 0.431035 0.027 Uiso 1 1 calc R U . . .
C12 C 0.18202(16) 0.0887(2) 0.50803(18) 0.0195(5) Uani 1 1 d . . . . .
C13 C 0.18851(16) 0.3121(2) 0.59211(18) 0.0193(5) Uani 1 1 d . . . . .
C14 C 0.11526(17) 0.3924(3) 0.58702(19) 0.0225(5) Uani 1 1 d . . . . .
H14A H 0.058522 0.352195 0.580548 0.027 Uiso 1 1 calc R U . . .
C15 C 0.12292(17) 0.5316(3) 0.59119(19) 0.0238(5) Uani 1 1 d . . . . .
H15A H 0.071403 0.583786 0.588806 0.029 Uiso 1 1 calc R U . . .
C16 C 0.20338(17) 0.5958(3) 0.59870(18) 0.0227(5) Uani 1 1 d . . . . .
H16A H 0.208319 0.690474 0.602524 0.027 Uiso 1 1 calc R U . . .
C17 C 0.27680(16) 0.5156(2) 0.60040(18) 0.0197(5) Uani 1 1 d . . . . .
C18 C 0.27073(16) 0.3737(2) 0.59832(18) 0.0193(5) Uani 1 1 d . . . . .
C19 C 0.40781(16) 0.4168(2) 0.61352(18) 0.0196(5) Uani 1 1 d . . . . .
C20 C 0.50366(16) 0.4074(2) 0.62948(17) 0.0188(5) Uani 1 1 d . . . . .
C21 C 0.54435(17) 0.2818(3) 0.63714(19) 0.0239(5) Uani 1 1 d . . . . .
H21A H 0.508624 0.203170 0.629740 0.029 Uiso 1 1 calc R U . . .
C22 C 0.63604(17) 0.2718(3) 0.6554(2) 0.0261(6) Uani 1 1 d . . . . .
H22A H 0.663757 0.186437 0.659455 0.031 Uiso 1 1 calc R U . . .
C23 C 0.68824(18) 0.3881(3) 0.6678(2) 0.0290(6) Uani 1 1 d . . . . .
H23A H 0.751765 0.381476 0.681319 0.035 Uiso 1 1 calc R U . . .
C24 C 0.64862(17) 0.5116(3) 0.6608(2) 0.0271(6) Uani 1 1 d . . . . .
H24A H 0.685241 0.589505 0.669554 0.033 Uiso 1 1 calc R U . . .
C25 C 0.55482(17) 0.5254(3) 0.64085(18) 0.0219(5) Uani 1 1 d . . . . .
C26 C 0.50879(16) 0.6548(2) 0.62930(18) 0.0212(5) Uani 1 1 d . . . . .
C27 C 0.55577(18) 0.7759(3) 0.6324(2) 0.0266(6) Uani 1 1 d . . . . .
H27A H 0.619404 0.773792 0.645682 0.032 Uiso 1 1 calc R U . . .
C28 C 0.51177(18) 0.8970(3) 0.6167(2) 0.0276(6) Uani 1 1 d . . . . .
H28A H 0.545138 0.977265 0.619724 0.033 Uiso 1 1 calc R U . . .
C29 C 0.41872(19) 0.9025(3) 0.5964(2) 0.0265(6) Uani 1 1 d . . . . .
H29A H 0.388205 0.986180 0.584696 0.032 Uiso 1 1 calc R U . . .
C30 C 0.37102(17) 0.7862(3) 0.59348(19) 0.0236(5) Uani 1 1 d . . . . .
H30A H 0.307288 0.789872 0.579175 0.028 Uiso 1 1 calc R U . . .
C31 C 0.41510(17) 0.6626(2) 0.61126(18) 0.0202(5) 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 1.396(3) . ?
N1 C12 1.405(3) . ?
N1 C13 1.424(3) . ?
N2 C19 1.314(3) . ?
N2 C18 1.378(3) . ?
N3 C19 1.385(3) . ?
N3 C17 1.404(3) . ?
N3 C31 1.419(3) . ?
C1 C2 1.391(3) . ?
C1 C6 1.411(3) . ?
C2 C3 1.389(4) . ?
C3 C4 1.399(4) . ?
C4 C5 1.381(4) . ?
C5 C6 1.394(3) . ?
C6 C7 1.448(3) . ?
C7 C8 1.397(3) . ?
C7 C12 1.408(3) . ?
C8 C9 1.384(4) . ?
C9 C10 1.398(4) . ?
C10 C11 1.378(4) . ?
C11 C12 1.390(3) . ?
C13 C14 1.380(3) . ?
C13 C18 1.401(3) . ?
C14 C15 1.396(4) . ?
C15 C16 1.384(4) . ?
C16 C17 1.392(3) . ?
C17 C18 1.421(3) . ?
C19 C20 1.443(3) . ?
C20 C21 1.395(4) . ?
C20 C25 1.404(3) . ?
C21 C22 1.374(4) . ?
C22 C23 1.398(4) . ?
C23 C24 1.370(4) . ?
C24 C25 1.406(3) . ?
C25 C26 1.463(4) . ?
C26 C31 1.404(3) . ?
C26 C27 1.409(4) . ?
C27 C28 1.374(4) . ?
C28 C29 1.388(4) . ?
C29 C30 1.374(4) . ?
C30 C31 1.397(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
C1 N1 C12 107.6(2) . . ?
C1 N1 C13 124.0(2) . . ?
C12 N1 C13 124.2(2) . . ?
C19 N2 C18 104.2(2) . . ?
C19 N3 C17 105.78(19) . . ?
C19 N3 C31 122.6(2) . . ?
C17 N3 C31 131.6(2) . . ?
C2 C1 N1 128.6(2) . . ?
C2 C1 C6 121.7(2) . . ?
N1 C1 C6 109.6(2) . . ?
C3 C2 C1 117.6(2) . . ?
C2 C3 C4 121.5(2) . . ?
C5 C4 C3 120.4(2) . . ?
C4 C5 C6 119.6(2) . . ?
C5 C6 C1 119.1(2) . . ?
C5 C6 C7 134.4(2) . . ?
C1 C6 C7 106.5(2) . . ?
C8 C7 C12 119.1(2) . . ?
C8 C7 C6 133.8(2) . . ?
C12 C7 C6 107.0(2) . . ?
C9 C8 C7 118.9(2) . . ?
C8 C9 C10 120.7(2) . . ?
C11 C10 C9 121.9(2) . . ?
C10 C11 C12 117.1(2) . . ?
C11 C12 N1 128.5(2) . . ?
C11 C12 C7 122.4(2) . . ?
N1 C12 C7 109.2(2) . . ?
C14 C13 C18 118.4(2) . . ?
C14 C13 N1 120.0(2) . . ?
C18 C13 N1 121.6(2) . . ?
C13 C14 C15 121.3(2) . . ?
C16 C15 C14 121.9(2) . . ?
C15 C16 C17 117.1(2) . . ?
C16 C17 N3 134.2(2) . . ?
C16 C17 C18 121.7(2) . . ?
N3 C17 C18 104.0(2) . . ?
N2 C18 C13 128.8(2) . . ?
N2 C18 C17 111.6(2) . . ?
C13 C18 C17 119.6(2) . . ?
N2 C19 N3 114.4(2) . . ?
N2 C19 C20 125.6(2) . . ?
N3 C19 C20 120.0(2) . . ?
C21 C20 C25 121.3(2) . . ?
C21 C20 C19 119.6(2) . . ?
C25 C20 C19 119.1(2) . . ?
C22 C21 C20 120.1(2) . . ?
C21 C22 C23 119.5(2) . . ?
C24 C23 C22 120.6(2) . . ?
C23 C24 C25 121.3(2) . . ?
C20 C25 C24 117.3(2) . . ?
C20 C25 C26 119.3(2) . . ?
C24 C25 C26 123.4(2) . . ?
C31 C26 C27 117.4(2) . . ?
C31 C26 C25 121.0(2) . . ?
C27 C26 C25 121.6(2) . . ?
C28 C27 C26 121.6(2) . . ?
C27 C28 C29 120.2(2) . . ?
C30 C29 C28 119.6(2) . . ?
C29 C30 C31 120.8(2) . . ?
C30 C31 C26 120.4(2) . . ?
C30 C31 N3 121.9(2) . . ?
C26 C31 N3 117.7(2) . . ?

_refine_diff_density_max         0.308
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.075

####################################################################### 
# 
# 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_ic19503
_database_code_depnum_ccdc_archive 'CCDC 1969130'
loop_
_audit_author_name
_audit_author_address
'Man-Kit Leung'
;National Taiwan University
Taiwan
;
_audit_update_record             
;
2019-11-30 deposited with the CCDC.	2020-01-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H19 N3'
_chemical_formula_weight         433.49

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

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

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

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

_cell_length_a                   9.4260(6)
_cell_length_b                   13.2378(7)
_cell_length_c                   18.0050(10)
_cell_angle_alpha                75.928(5)
_cell_angle_beta                 77.538(5)
_cell_angle_gamma                88.703(4)
_cell_volume                     2126.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3745
_cell_measurement_theta_min      3.5910
_cell_measurement_theta_max      27.0130

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_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  0.85317
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2496
_diffrn_reflns_number            14637
_diffrn_reflns_av_unetI/netI     0.0822
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.107
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             9240
_reflns_number_gt                5432
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0497P)²+0.4404P] 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         9240
_refine_ls_number_parameters     613
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1267
_refine_ls_R_factor_gt           0.0617
_refine_ls_wR_factor_ref         0.1519
_refine_ls_wR_factor_gt          0.1149
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.7822(2) 0.04708(15) 0.96075(12) 0.0308(5) Uani 1 1 d . . . . .
N2 N 0.69290(19) 0.20906(15) 0.95083(12) 0.0321(5) Uani 1 1 d . . . . .
N3 N 0.79843(19) 0.36103(15) 0.81556(12) 0.0300(5) Uani 1 1 d . . . . .
C1 C 0.6630(2) 0.03956(19) 1.02414(15) 0.0315(6) Uani 1 1 d . . . . .
C2 C 0.5925(3) -0.0423(2) 1.08517(16) 0.0393(7) Uani 1 1 d . . . . .
H2A H 0.623989 -0.111865 1.090311 0.047 Uiso 1 1 calc R U . . .
C3 C 0.4751(3) -0.0172(2) 1.13758(16) 0.0419(7) Uani 1 1 d . . . . .
H3A H 0.425482 -0.071213 1.179678 0.050 Uiso 1 1 calc R U . . .
C4 C 0.4267(3) 0.0841(2) 1.13106(16) 0.0418(7) Uani 1 1 d . . . . .
H4A H 0.346537 0.097910 1.168958 0.050 Uiso 1 1 calc R U . . .
C5 C 0.4940(3) 0.1644(2) 1.07024(15) 0.0378(6) Uani 1 1 d . . . . .
H5A H 0.460575 0.233505 1.065011 0.045 Uiso 1 1 calc R U . . .
C6 C 0.6126(2) 0.14104(19) 1.01662(14) 0.0308(6) Uani 1 1 d . . . . .
C7 C 0.7913(2) 0.15162(18) 0.91872(15) 0.0294(6) Uani 1 1 d . . . . .
C8 C 0.9013(2) 0.18544(19) 0.84735(15) 0.0301(6) Uani 1 1 d . . . . .
C9 C 0.9063(2) 0.28759(19) 0.79875(15) 0.0314(6) Uani 1 1 d . . . . .
C10 C 1.0148(2) 0.3177(2) 0.73224(16) 0.0386(7) Uani 1 1 d . . . . .
H10A H 1.017983 0.386508 0.700112 0.046 Uiso 1 1 calc R U . . .
C11 C 1.1201(3) 0.2478(2) 0.71185(17) 0.0424(7) Uani 1 1 d . . . . .
H11A H 1.195365 0.269176 0.666257 0.051 Uiso 1 1 calc R U . . .
C12 C 1.1150(3) 0.1484(2) 0.75742(17) 0.0410(7) Uani 1 1 d . . . . .
H12A H 1.186624 0.101217 0.742422 0.049 Uiso 1 1 calc R U . . .
C13 C 1.0066(2) 0.1140(2) 0.82587(15) 0.0336(6) Uani 1 1 d . . . . .
C14 C 1.0001(3) 0.0072(2) 0.87539(16) 0.0360(6) Uani 1 1 d . . . . .
C15 C 1.1072(3) -0.0652(2) 0.85926(18) 0.0433(7) Uani 1 1 d . . . . .
H15A H 1.185086 -0.045037 0.814770 0.052 Uiso 1 1 calc R U . . .
C16 C 1.1014(3) -0.1645(2) 0.9066(2) 0.0495(8) Uani 1 1 d . . . . .
H16A H 1.175117 -0.211867 0.894771 0.059 Uiso 1 1 calc R U . . .
C17 C 0.9888(3) -0.1953(2) 0.97124(19) 0.0484(8) Uani 1 1 d . . . . .
H17A H 0.985268 -0.263951 1.003698 0.058 Uiso 1 1 calc R U . . .
C18 C 0.8810(3) -0.1269(2) 0.98908(18) 0.0423(7) Uani 1 1 d . . . . .
H18A H 0.803361 -0.148713 1.033488 0.051 Uiso 1 1 calc R U . . .
C19 C 0.8864(3) -0.02583(19) 0.94166(16) 0.0342(6) Uani 1 1 d . . . . .
C20 C 0.8061(3) 0.43246(18) 0.86000(15) 0.0316(6) Uani 1 1 d . . . . .
C21 C 0.9271(3) 0.46825(19) 0.87984(15) 0.0371(6) Uani 1 1 d . . . . .
H21A H 1.020689 0.441806 0.864856 0.044 Uiso 1 1 calc R U . . .
C22 C 0.9064(3) 0.5436(2) 0.92211(16) 0.0431(7) Uani 1 1 d . . . . .
H22A H 0.987611 0.569833 0.935848 0.052 Uiso 1 1 calc R U . . .
C23 C 0.7692(3) 0.5822(2) 0.94512(16) 0.0447(7) Uani 1 1 d . . . . .
H23A H 0.757963 0.633489 0.974608 0.054 Uiso 1 1 calc R U . . .
C24 C 0.6493(3) 0.54607(19) 0.92521(15) 0.0398(7) Uani 1 1 d . . . . .
H24A H 0.556017 0.572354 0.941052 0.048 Uiso 1 1 calc R U . . .
C25 C 0.6662(3) 0.47131(18) 0.88200(15) 0.0324(6) Uani 1 1 d . . . . .
C26 C 0.5689(2) 0.41961(18) 0.84937(14) 0.0320(6) Uani 1 1 d . . . . .
C27 C 0.4205(3) 0.4239(2) 0.85097(15) 0.0367(6) Uani 1 1 d . . . . .
H27A H 0.361292 0.469435 0.876916 0.044 Uiso 1 1 calc R U . . .
C28 C 0.3611(3) 0.3605(2) 0.81407(16) 0.0406(7) Uani 1 1 d . . . . .
H28A H 0.259468 0.361108 0.816184 0.049 Uiso 1 1 calc R U . . .
C29 C 0.4478(2) 0.2959(2) 0.77386(16) 0.0390(7) Uani 1 1 d . . . . .
H29A H 0.404730 0.254026 0.748185 0.047 Uiso 1 1 calc R U . . .
C30 C 0.5961(2) 0.29167(19) 0.77065(15) 0.0340(6) Uani 1 1 d . . . . .
H30A H 0.655631 0.248219 0.742730 0.041 Uiso 1 1 calc R U . . .
C31 C 0.6540(2) 0.35281(18) 0.80947(14) 0.0290(6) Uani 1 1 d . . . . .
N4 N 0.71949(19) 0.96007(14) 0.50869(11) 0.0265(5) Uani 1 1 d . . . . .
N5 N 0.6206(2) 0.79731(15) 0.53538(12) 0.0317(5) Uani 1 1 d . . . . .
N6 N 0.63864(19) 0.65867(15) 0.67569(12) 0.0313(5) Uani 1 1 d . . . . .
C32 C 0.6525(2) 0.95751(18) 0.44671(14) 0.0271(5) Uani 1 1 d . . . . .
C33 C 0.6338(2) 1.02916(19) 0.37862(15) 0.0337(6) Uani 1 1 d . . . . .
H33A H 0.673870 1.098100 0.364925 0.040 Uiso 1 1 calc DR U . . .
C34 C 0.5554(3) 0.9966(2) 0.33216(15) 0.0359(6) Uani 1 1 d . . . . .
H34A H 0.542053 1.044147 0.285516 0.043 Uiso 1 1 calc R U . . .
C35 C 0.4948(3) 0.8960(2) 0.35119(15) 0.0364(6) Uani 1 1 d . . . . .
H35A H 0.440058 0.876685 0.317962 0.044 Uiso 1 1 calc R U . . .
C36 C 0.5135(2) 0.82450(19) 0.41757(15) 0.0337(6) Uani 1 1 d . . . . .
H36A H 0.473639 0.755596 0.430303 0.040 Uiso 1 1 calc R U . . .
C37 C 0.5924(2) 0.85554(18) 0.46570(14) 0.0290(6) Uani 1 1 d . . . . .
C38 C 0.6954(2) 0.86065(17) 0.55958(14) 0.0267(5) Uani 1 1 d . . . . .
C39 C 0.7537(2) 0.83682(18) 0.62949(14) 0.0275(5) Uani 1 1 d . . . . .
C40 C 0.7301(2) 0.73809(18) 0.68403(15) 0.0302(6) Uani 1 1 d . . . . .
C41 C 0.7941(2) 0.7170(2) 0.74782(16) 0.0363(6) Uani 1 1 d . . . . .
H41A H 0.779862 0.650168 0.783312 0.044 Uiso 1 1 calc R U . . .
C42 C 0.8792(2) 0.7925(2) 0.76073(16) 0.0371(6) Uani 1 1 d . . . . .
H42A H 0.922273 0.777255 0.805136 0.045 Uiso 1 1 calc R U . . .
C43 C 0.9014(2) 0.8892(2) 0.70940(15) 0.0347(6) Uani 1 1 d . . . . .
H43A H 0.959658 0.940309 0.718923 0.042 Uiso 1 1 calc R U . . .
C44 C 0.8396(2) 0.91363(18) 0.64322(14) 0.0283(6) Uani 1 1 d . . . . .
C45 C 0.8632(2) 1.01691(18) 0.58776(14) 0.0286(6) Uani 1 1 d . . . . .
C46 C 0.9477(2) 1.09579(19) 0.59865(16) 0.0373(6) Uani 1 1 d . . . . .
H46A H 0.990216 1.082465 0.643242 0.045 Uiso 1 1 calc R U . . .
C47 C 0.9709(3) 1.1923(2) 0.54624(17) 0.0408(7) Uani 1 1 d . . . . .
H47A H 1.029210 1.244432 0.554499 0.049 Uiso 1 1 calc R U . . .
C48 C 0.9084(3) 1.2123(2) 0.48177(16) 0.0388(7) Uani 1 1 d . . . . .
H48A H 0.923759 1.278578 0.445625 0.047 Uiso 1 1 calc R U . . .
C49 C 0.8245(2) 1.13760(18) 0.46926(15) 0.0346(6) Uani 1 1 d . . . . .
H49A H 0.781140 1.152786 0.424957 0.042 Uiso 1 1 calc DR U . . .
C50 C 0.8022(2) 1.03933(17) 0.52118(14) 0.0269(5) Uani 1 1 d . . . . .
C51 C 0.6837(3) 0.58343(18) 0.63429(15) 0.0340(6) Uani 1 1 d . . . . .
C52 C 0.8225(3) 0.5502(2) 0.60992(17) 0.0438(7) Uani 1 1 d . . . . .
H52A H 0.905111 0.581513 0.618614 0.053 Uiso 1 1 calc R U . . .
C53 C 0.8363(3) 0.4697(2) 0.57247(18) 0.0535(9) Uani 1 1 d . . . . .
H53A H 0.930173 0.444333 0.556455 0.064 Uiso 1 1 calc R U . . .
C54 C 0.7161(3) 0.4248(2) 0.55756(19) 0.0576(9) Uani 1 1 d . . . . .
H54A H 0.729632 0.370866 0.530480 0.069 Uiso 1 1 calc R U . . .
C55 C 0.5782(3) 0.4580(2) 0.58177(17) 0.0486(8) Uani 1 1 d . . . . .
H55A H 0.496431 0.427300 0.571678 0.058 Uiso 1 1 calc R U . . .
C56 C 0.5604(3) 0.53727(19) 0.62125(15) 0.0363(6) Uani 1 1 d . . . . .
C57 C 0.4348(2) 0.58648(18) 0.65740(15) 0.0333(6) Uani 1 1 d . . . . .
C58 C 0.2853(3) 0.5720(2) 0.66677(16) 0.0402(7) Uani 1 1 d . . . . .
H58A H 0.248169 0.522962 0.644431 0.048 Uiso 1 1 calc R U . . .
C59 C 0.1921(3) 0.6299(2) 0.70902(16) 0.0414(7) Uani 1 1 d . . . . .
H59A H 0.090110 0.621478 0.715146 0.050 Uiso 1 1 calc R U . . .
C60 C 0.2464(3) 0.7010(2) 0.74290(16) 0.0428(7) Uani 1 1 d . . . . .
H60A H 0.180240 0.739341 0.772347 0.051 Uiso 1 1 calc R U . . .
C61 C 0.3942(3) 0.71673(19) 0.73461(15) 0.0363(6) Uani 1 1 d . . . . .
H61A H 0.430565 0.764752 0.758056 0.044 Uiso 1 1 calc R U . . .
C62 C 0.4871(2) 0.65979(18) 0.69080(14) 0.0310(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 C7 1.401(3) . ?
N1 C1 1.404(3) . ?
N1 C19 1.410(3) . ?
N2 C7 1.313(3) . ?
N2 C6 1.383(3) . ?
N3 C20 1.391(3) . ?
N3 C31 1.398(3) . ?
N3 C9 1.427(3) . ?
C1 C6 1.400(3) . ?
C1 C2 1.401(3) . ?
C2 C3 1.382(4) . ?
C3 C4 1.393(4) . ?
C4 C5 1.377(3) . ?
C5 C6 1.393(3) . ?
C7 C8 1.447(3) . ?
C8 C13 1.414(3) . ?
C8 C9 1.416(3) . ?
C9 C10 1.377(3) . ?
C10 C11 1.394(4) . ?
C11 C12 1.367(4) . ?
C12 C13 1.405(4) . ?
C13 C14 1.472(4) . ?
C14 C19 1.407(4) . ?
C14 C15 1.409(3) . ?
C15 C16 1.377(4) . ?
C16 C17 1.379(4) . ?
C17 C18 1.384(4) . ?
C18 C19 1.397(3) . ?
C20 C21 1.391(3) . ?
C20 C25 1.415(3) . ?
C21 C22 1.382(4) . ?
C22 C23 1.395(4) . ?
C23 C24 1.384(4) . ?
C24 C25 1.387(4) . ?
C25 C26 1.453(4) . ?
C26 C27 1.394(3) . ?
C26 C31 1.403(3) . ?
C27 C28 1.382(4) . ?
C28 C29 1.392(4) . ?
C29 C30 1.387(3) . ?
C30 C31 1.379(3) . ?
N4 C38 1.400(3) . ?
N4 C32 1.403(3) . ?
N4 C50 1.410(3) . ?
N5 C38 1.314(3) . ?
N5 C37 1.380(3) . ?
N6 C51 1.390(3) . ?
N6 C62 1.396(3) . ?
N6 C40 1.430(3) . ?
C32 C33 1.398(3) . ?
C32 C37 1.409(3) . ?
C33 C34 1.374(4) . ?
C34 C35 1.395(3) . ?
C35 C36 1.374(4) . ?
C36 C37 1.392(3) . ?
C38 C39 1.443(3) . ?
C39 C44 1.413(3) . ?
C39 C40 1.420(3) . ?
C40 C41 1.377(3) . ?
C41 C42 1.388(4) . ?
C42 C43 1.375(3) . ?
C43 C44 1.403(3) . ?
C44 C45 1.473(3) . ?
C45 C46 1.403(3) . ?
C45 C50 1.404(3) . ?
C46 C47 1.382(3) . ?
C47 C48 1.380(4) . ?
C48 C49 1.369(3) . ?
C49 C50 1.395(3) . ?
C51 C52 1.385(3) . ?
C51 C56 1.414(3) . ?
C52 C53 1.382(4) . ?
C53 C54 1.396(4) . ?
C54 C55 1.377(4) . ?
C55 C56 1.392(4) . ?
C56 C57 1.445(4) . ?
C57 C58 1.395(3) . ?
C57 C62 1.407(4) . ?
C58 C59 1.380(4) . ?
C59 C60 1.398(4) . ?
C60 C61 1.384(3) . ?
C61 C62 1.385(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 105.51(19) . . ?
C7 N1 C19 122.7(2) . . ?
C1 N1 C19 131.5(2) . . ?
C7 N2 C6 105.0(2) . . ?
C20 N3 C31 108.02(19) . . ?
C20 N3 C9 125.6(2) . . ?
C31 N3 C9 124.1(2) . . ?
C6 C1 C2 120.5(2) . . ?
C6 C1 N1 104.88(19) . . ?
C2 C1 N1 134.6(2) . . ?
C3 C2 C1 117.0(2) . . ?
C2 C3 C4 122.5(2) . . ?
C5 C4 C3 120.7(3) . . ?
C4 C5 C6 117.8(3) . . ?
N2 C6 C5 127.1(2) . . ?
N2 C6 C1 111.4(2) . . ?
C5 C6 C1 121.5(2) . . ?
N2 C7 N1 113.2(2) . . ?
N2 C7 C8 127.0(2) . . ?
N1 C7 C8 119.8(2) . . ?
C13 C8 C9 119.3(2) . . ?
C13 C8 C7 118.7(2) . . ?
C9 C8 C7 122.0(2) . . ?
C10 C9 C8 120.3(2) . . ?
C10 C9 N3 118.1(2) . . ?
C8 C9 N3 121.6(2) . . ?
C9 C10 C11 120.3(2) . . ?
C12 C11 C10 120.0(2) . . ?
C11 C12 C13 121.8(2) . . ?
C12 C13 C8 118.3(2) . . ?
C12 C13 C14 122.2(2) . . ?
C8 C13 C14 119.5(2) . . ?
C19 C14 C15 117.5(2) . . ?
C19 C14 C13 120.6(2) . . ?
C15 C14 C13 121.8(2) . . ?
C16 C15 C14 121.4(3) . . ?
C15 C16 C17 120.1(3) . . ?
C16 C17 C18 120.4(3) . . ?
C17 C18 C19 119.9(3) . . ?
C18 C19 C14 120.7(2) . . ?
C18 C19 N1 121.0(2) . . ?
C14 C19 N1 118.2(2) . . ?
C21 C20 N3 129.0(2) . . ?
C21 C20 C25 121.7(2) . . ?
N3 C20 C25 109.3(2) . . ?
C22 C21 C20 117.7(2) . . ?
C21 C22 C23 121.6(3) . . ?
C24 C23 C22 120.4(3) . . ?
C23 C24 C25 119.6(3) . . ?
C24 C25 C20 119.0(2) . . ?
C24 C25 C26 134.4(2) . . ?
C20 C25 C26 106.5(2) . . ?
C27 C26 C31 119.3(2) . . ?
C27 C26 C25 134.0(2) . . ?
C31 C26 C25 106.7(2) . . ?
C28 C27 C26 118.7(2) . . ?
C27 C28 C29 121.0(2) . . ?
C30 C29 C28 121.1(3) . . ?
C31 C30 C29 117.5(2) . . ?
C30 C31 N3 128.2(2) . . ?
C30 C31 C26 122.3(2) . . ?
N3 C31 C26 109.5(2) . . ?
C38 N4 C32 105.82(18) . . ?
C38 N4 C50 123.0(2) . . ?
C32 N4 C50 131.08(19) . . ?
C38 N5 C37 105.03(19) . . ?
C51 N6 C62 108.2(2) . . ?
C51 N6 C40 125.49(18) . . ?
C62 N6 C40 124.6(2) . . ?
C33 C32 N4 135.4(2) . . ?
C33 C32 C37 120.1(2) . . ?
N4 C32 C37 104.49(19) . . ?
C34 C33 C32 117.8(2) . . ?
C33 C34 C35 122.2(2) . . ?
C36 C35 C34 120.6(2) . . ?
C35 C36 C37 118.4(2) . . ?
N5 C37 C36 127.6(2) . . ?
N5 C37 C32 111.5(2) . . ?
C36 C37 C32 120.9(2) . . ?
N5 C38 N4 113.2(2) . . ?
N5 C38 C39 127.1(2) . . ?
N4 C38 C39 119.7(2) . . ?
C44 C39 C40 118.9(2) . . ?
C44 C39 C38 118.9(2) . . ?
C40 C39 C38 122.2(2) . . ?
C41 C40 C39 120.2(2) . . ?
C41 C40 N6 118.0(2) . . ?
C39 C40 N6 121.8(2) . . ?
C40 C41 C42 120.6(2) . . ?
C43 C42 C41 120.2(3) . . ?
C42 C43 C44 121.1(2) . . ?
C43 C44 C39 119.0(2) . . ?
C43 C44 C45 121.5(2) . . ?
C39 C44 C45 119.5(2) . . ?
C46 C45 C50 117.6(2) . . ?
C46 C45 C44 121.8(2) . . ?
C50 C45 C44 120.7(2) . . ?
C47 C46 C45 121.7(3) . . ?
C48 C47 C46 119.3(2) . . ?
C49 C48 C47 120.8(2) . . ?
C48 C49 C50 120.4(3) . . ?
C49 C50 C45 120.2(2) . . ?
C49 C50 N4 121.6(2) . . ?
C45 C50 N4 118.15(19) . . ?
C52 C51 N6 129.4(2) . . ?
C52 C51 C56 121.4(3) . . ?
N6 C51 C56 109.1(2) . . ?
C53 C52 C51 117.6(3) . . ?
C52 C53 C54 121.8(3) . . ?
C55 C54 C53 120.6(3) . . ?
C54 C55 C56 118.9(3) . . ?
C55 C56 C51 119.7(2) . . ?
C55 C56 C57 133.6(2) . . ?
C51 C56 C57 106.7(2) . . ?
C58 C57 C62 119.5(2) . . ?
C58 C57 C56 133.7(3) . . ?
C62 C57 C56 106.7(2) . . ?
C59 C58 C57 118.9(3) . . ?
C58 C59 C60 120.6(2) . . ?
C61 C60 C59 121.6(3) . . ?
C60 C61 C62 117.4(3) . . ?
C61 C62 N6 128.7(2) . . ?
C61 C62 C57 121.9(2) . . ?
N6 C62 C57 109.2(2) . . ?

_refine_diff_density_max         0.572
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.051

