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

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

data_hz_2_0m_a_sq
_audit_block_doi                 10.5517/ccdc.csd.cc284vlw
_database_code_depnum_ccdc_archive 'CCDC 2090038'
loop_
_audit_author_name
_audit_author_address
'jun lin'
;Yunnan University
China
;
_audit_update_record             
;
2021-06-15 deposited with the CCDC.	2021-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
3'-azido-2'-(1H-benzo[d]imidazol-1-yl)-1H,3'H-3,3'-biindole
_chemical_name_common            ?
_chemical_melting_point          486
_chemical_formula_moiety         C23H15N7
_chemical_formula_sum            C23H15N7
_chemical_formula_weight         527.04

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.6842(17)
_cell_length_b                   10.8749(17)
_cell_length_c                   12.429(2)
_cell_angle_alpha                91.808(2)
_cell_angle_beta                 111.391(2)
_cell_angle_gamma                101.478(2)
_cell_volume                     1309.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2350
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      21.57

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_F_000             546
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12261
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.923
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5904
_reflns_number_gt                3171
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5904
_refine_ls_number_parameters     271
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1128
_refine_ls_R_factor_gt           0.0669
_refine_ls_wR_factor_ref         0.2246
_refine_ls_wR_factor_gt          0.1995
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_restrained_S_all      1.207
_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
N2 N 0.5837(2) 0.72375(19) 0.1132(2) 0.0898(7) Uani 1 1 d . . . . .
N3 N 0.66621(19) 0.25192(18) 0.07760(16) 0.0727(6) Uani 1 1 d . . . . .
H3A H 0.592359 0.221679 0.017530 0.087 Uiso 1 1 calc R U . . .
N4 N 0.84533(16) 0.38781(16) 0.20888(14) 0.0581(5) Uani 1 1 d . . . . .
N5 N 1.04123(17) 0.51129(17) 0.35630(15) 0.0641(5) Uani 1 1 d . . . . .
N6 N 1.1380(5) 0.6632(5) 0.0800(4) 0.208(2) Uani 1 1 d . U . . .
N7 N 1.0380(4) 0.6434(3) 0.0925(2) 0.1063(8) Uani 1 1 d . . . . .
N8 N 0.9255(3) 0.6171(2) 0.09333(18) 0.0934(7) Uani 1 1 d . . . . .
C1 C 0.6945(3) 0.6982(2) 0.0953(2) 0.0794(7) Uani 1 1 d . . . . .
H1 H 0.709249 0.706152 0.026342 0.095 Uiso 1 1 calc R U . . .
C2 C 0.7191(2) 0.6605(2) 0.2771(2) 0.0650(6) Uani 1 1 d . . . . .
C3 C 0.7562(3) 0.6326(3) 0.3919(2) 0.0830(8) Uani 1 1 d . . . . .
H3 H 0.836507 0.604463 0.428149 0.100 Uiso 1 1 calc R U . . .
C4 C 0.6726(3) 0.6473(4) 0.4501(3) 0.1241(12) Uani 1 1 d . . . . .
H4 H 0.695921 0.628115 0.526408 0.149 Uiso 1 1 calc R U . . .
C5 C 0.5531(4) 0.6906(5) 0.3966(4) 0.1428(15) Uani 1 1 d . . . . .
H5 H 0.499327 0.701629 0.438855 0.171 Uiso 1 1 calc R U . . .
C6 C 0.5122(3) 0.7175(3) 0.2844(4) 0.1160(11) Uani 1 1 d . . . . .
H6 H 0.431135 0.744871 0.248935 0.139 Uiso 1 1 calc R U . . .
C7 C 0.5961(2) 0.7022(2) 0.2259(3) 0.0801(7) Uani 1 1 d . . . . .
C8 C 0.9360(2) 0.5025(2) 0.26338(18) 0.0566(5) Uani 1 1 d . . . . .
C9 C 0.9159(2) 0.6273(2) 0.21047(17) 0.0621(6) Uani 1 1 d . . . . .
C10 C 1.0397(2) 0.7143(2) 0.30211(19) 0.0641(6) Uani 1 1 d . . . . .
C11 C 1.0887(3) 0.8421(3) 0.3122(2) 0.0831(7) Uani 1 1 d . . . . .
H11 H 1.042958 0.891155 0.257867 0.100 Uiso 1 1 calc R U . . .
C12 C 1.2103(3) 0.8965(3) 0.4075(3) 0.0974(9) Uani 1 1 d . . . . .
H12 H 1.246458 0.983056 0.416423 0.117 Uiso 1 1 calc R U . . .
C13 C 1.2762(3) 0.8241(3) 0.4872(3) 0.0947(9) Uani 1 1 d . . . . .
H13 H 1.356016 0.862669 0.550020 0.114 Uiso 1 1 calc R U . . .
C14 C 1.2279(2) 0.6953(3) 0.4773(2) 0.0810(7) Uani 1 1 d . . . . .
H14 H 1.273843 0.646558 0.531781 0.097 Uiso 1 1 calc R U . . .
C15 C 1.1085(2) 0.6414(2) 0.38327(19) 0.0647(6) Uani 1 1 d . . . . .
C16 C 0.7303(2) 0.3685(2) 0.10861(19) 0.0662(6) Uani 1 1 d . . . . .
H16 H 0.701075 0.433693 0.066649 0.079 Uiso 1 1 calc R U . . .
C17 C 0.7413(2) 0.1853(2) 0.16142(19) 0.0647(6) Uani 1 1 d . . . . .
C18 C 0.8539(2) 0.2675(2) 0.24492(18) 0.0580(5) Uani 1 1 d . . . . .
C19 C 0.9475(2) 0.2265(2) 0.33860(19) 0.0707(6) Uani 1 1 d . . . . .
H19 H 1.023174 0.282270 0.393662 0.085 Uiso 1 1 calc R U . . .
C20 C 0.9221(3) 0.0998(3) 0.3455(2) 0.0890(8) Uani 1 1 d . . . . .
H20 H 0.982656 0.067940 0.406747 0.107 Uiso 1 1 calc R U . . .
C21 C 0.8082(3) 0.0166(3) 0.2634(3) 0.0951(9) Uani 1 1 d . . . . .
H21 H 0.794110 -0.069126 0.271868 0.114 Uiso 1 1 calc R U . . .
C22 C 0.7173(3) 0.0571(2) 0.1714(3) 0.0867(8) Uani 1 1 d . . . . .
H22 H 0.641479 0.000860 0.116972 0.104 Uiso 1 1 calc R U . . .
C23 C 0.7812(2) 0.65906(19) 0.19237(18) 0.0615(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
N2 C1 1.359(3) . ?
N2 C7 1.390(4) . ?
N3 C16 1.287(3) . ?
N3 C17 1.387(3) . ?
N3 H3A 0.8600 . ?
N4 C16 1.368(3) . ?
N4 C8 1.393(3) . ?
N4 C18 1.406(3) . ?
N5 C8 1.269(2) . ?
N5 C15 1.421(3) . ?
N6 N7 1.115(4) . ?
N7 N8 1.184(3) . ?
N8 C9 1.499(3) . ?
C1 C23 1.367(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.395(3) . ?
C2 C7 1.408(3) . ?
C2 C23 1.436(3) . ?
C3 C4 1.367(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.361(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.373(4) . ?
C6 H6 0.9300 . ?
C8 C9 1.546(3) . ?
C9 C23 1.486(3) . ?
C9 C10 1.509(3) . ?
C10 C11 1.368(3) . ?
C10 C15 1.389(3) . ?
C11 C12 1.403(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.363(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.381(3) . ?
C14 H14 0.9300 . ?
C16 H16 0.9300 . ?
C17 C22 1.384(3) . ?
C17 C18 1.388(3) . ?
C18 C19 1.383(3) . ?
C19 C20 1.362(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.393(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.355(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N2 C7 108.9(2) . . ?
C16 N3 C17 105.50(18) . . ?
C16 N3 H3A 127.3 . . ?
C17 N3 H3A 127.3 . . ?
C16 N4 C8 127.26(18) . . ?
C16 N4 C18 105.63(17) . . ?
C8 N4 C18 127.11(17) . . ?
C8 N5 C15 106.35(18) . . ?
N6 N7 N8 172.8(4) . . ?
N7 N8 C9 116.1(2) . . ?
N2 C1 C23 110.8(2) . . ?
N2 C1 H1 124.6 . . ?
C23 C1 H1 124.6 . . ?
C3 C2 C7 118.3(2) . . ?
C3 C2 C23 134.2(2) . . ?
C7 C2 C23 107.5(2) . . ?
C4 C3 C2 119.0(2) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 122.3(3) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C5 C6 C7 116.9(3) . . ?
C5 C6 H6 121.6 . . ?
C7 C6 H6 121.6 . . ?
C6 C7 N2 130.3(3) . . ?
C6 C7 C2 122.8(3) . . ?
N2 C7 C2 106.8(3) . . ?
N5 C8 N4 122.88(19) . . ?
N5 C8 C9 115.95(19) . . ?
N4 C8 C9 121.14(17) . . ?
C23 C9 N8 106.65(18) . . ?
C23 C9 C10 115.14(18) . . ?
N8 C9 C10 113.73(19) . . ?
C23 C9 C8 115.35(17) . . ?
N8 C9 C8 108.18(18) . . ?
C10 C9 C8 97.68(16) . . ?
C11 C10 C15 121.0(2) . . ?
C11 C10 C9 131.0(2) . . ?
C15 C10 C9 108.0(2) . . ?
C10 C11 C12 117.6(3) . . ?
C10 C11 H11 121.2 . . ?
C12 C11 H11 121.2 . . ?
C13 C12 C11 120.8(3) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 121.9(3) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C13 C14 C15 117.4(2) . . ?
C13 C14 H14 121.3 . . ?
C15 C14 H14 121.3 . . ?
C14 C15 C10 121.2(2) . . ?
C14 C15 N5 126.8(2) . . ?
C10 C15 N5 112.02(19) . . ?
N3 C16 N4 113.90(19) . . ?
N3 C16 H16 123.0 . . ?
N4 C16 H16 123.0 . . ?
C22 C17 N3 129.8(2) . . ?
C22 C17 C18 120.0(2) . . ?
N3 C17 C18 110.2(2) . . ?
C19 C18 C17 122.6(2) . . ?
C19 C18 N4 132.6(2) . . ?
C17 C18 N4 104.80(17) . . ?
C20 C19 C18 116.1(2) . . ?
C20 C19 H19 122.0 . . ?
C18 C19 H19 122.0 . . ?
C19 C20 C21 121.9(2) . . ?
C19 C20 H20 119.1 . . ?
C21 C20 H20 119.1 . . ?
C22 C21 C20 121.8(2) . . ?
C22 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
C21 C22 C17 117.6(2) . . ?
C21 C22 H22 121.2 . . ?
C17 C22 H22 121.2 . . ?
C1 C23 C2 106.0(2) . . ?
C1 C23 C9 127.8(2) . . ?
C2 C23 C9 126.20(17) . . ?

_refine_diff_density_max         0.312
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.036



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/Hexyl hydride'
####################################################################### 
# 
# 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_mo_210824_09066_0m
_database_code_depnum_ccdc_archive 'CCDC 2105161'
loop_
_audit_author_name
_audit_author_address
'jun lin'
;Yunnan University
China
;
_audit_update_record             
;
2021-08-24 deposited with the CCDC.	2021-08-25 downloaded from the CCDC.
;
_audit_creation_date             2021-08-24
_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        
3'-azido-7,7'-dimethyl-2'-(4-methyl-1H-imidazol-1-yl)-1H,3'H-3,3'-biindole
_chemical_formula_moiety         'C22 H19 N7'
_chemical_formula_sum            'C22 H19 N7'
_chemical_formula_weight         381.44
_chemical_melting_point          417
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.0191(10)
_cell_length_b                   10.4708(13)
_cell_length_c                   13.0070(16)
_cell_angle_alpha                68.608(5)
_cell_angle_beta                 84.564(5)
_cell_angle_gamma                75.181(4)
_cell_volume                     983.1(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4225
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.75
_cell_measurement_theta_min      2.63
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.994
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0994 before and 0.0525 after correction.
The Ratio of minimum to maximum transmission is 0.9030.
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    1.289
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14068
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.147
_diffrn_reflns_theta_min         2.213
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2681
_reflns_number_total             4139
_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 V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_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         0.200
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         4139
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0514
_refine_ls_restrained_S_all      1.040
_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)+(0.0617P)²+0.2241P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1445
_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. Restrained distances
 N7-H7
 0.88 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C10(H10), C12(H12), C15(H15), C18(H18), C19(H19),
 C20(H20)
3.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C13(H13A,H13B,H13C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.29358(19) 0.53207(19) 0.57224(14) 0.0437(4) Uani 1 1 d . . . . .
N2 N 0.44611(19) 0.39906(17) 0.73686(13) 0.0376(4) Uani 1 1 d . . . . .
N3 N 0.5866(2) 0.24307(18) 0.88768(14) 0.0427(4) Uani 1 1 d . . . . .
N4 N 0.5691(2) 0.6709(2) 0.65902(15) 0.0514(5) Uani 1 1 d . . . . .
N5 N 0.6329(2) 0.72397(19) 0.56899(16) 0.0481(5) Uani 1 1 d . . . . .
N6 N 0.7087(3) 0.7701(3) 0.4922(2) 0.0746(7) Uani 1 1 d . . . . .
N7 N 0.2620(2) 0.76367(19) 0.90924(15) 0.0440(4) Uani 1 1 d D . . . .
C1 C 0.1417(3) 0.7331(3) 0.41028(18) 0.0529(6) Uani 1 1 d . . . . .
C2 C 0.1019(3) 0.8803(3) 0.3598(2) 0.0661(8) Uani 1 1 d . . . . .
H2 H 0.036833 0.922851 0.293397 0.079 Uiso 1 1 calc R . . . .
C3 C 0.1543(3) 0.9657(3) 0.4034(2) 0.0678(8) Uani 1 1 d . . . . .
H3 H 0.126062 1.065065 0.365600 0.081 Uiso 1 1 calc R . . . .
C4 C 0.2479(3) 0.9098(2) 0.5019(2) 0.0570(6) Uani 1 1 d . . . . .
H4 H 0.282134 0.968558 0.532727 0.068 Uiso 1 1 calc R . . . .
C5 C 0.2880(2) 0.7644(2) 0.55202(17) 0.0444(5) Uani 1 1 d . . . . .
C6 C 0.2375(2) 0.6790(2) 0.50658(17) 0.0437(5) Uani 1 1 d . . . . .
C7 C 0.3712(2) 0.5271(2) 0.65529(16) 0.0380(5) Uani 1 1 d . . . . .
C8 C 0.3828(2) 0.6705(2) 0.65896(17) 0.0398(5) Uani 1 1 d . . . . .
C9 C 0.0856(3) 0.6410(3) 0.3626(2) 0.0689(8) Uani 1 1 d . . . . .
H9A H 0.170052 0.621173 0.307429 0.103 Uiso 1 1 calc GR . . . .
H9B H -0.027329 0.689196 0.327459 0.103 Uiso 1 1 calc GR . . . .
H9C H 0.077409 0.552028 0.421529 0.103 Uiso 1 1 calc GR . . . .
H7 H 0.291(4) 0.776(3) 0.9697(18) 0.083 Uiso 1 1 d DR . . . .
C10 C 0.5252(2) 0.3775(2) 0.83250(16) 0.0395(5) Uani 1 1 d . . . . .
H10 H 0.534431 0.451287 0.856061 0.047 Uiso 1 1 calc R . . . .
C11 C 0.5451(3) 0.1722(2) 0.82514(18) 0.0433(5) Uani 1 1 d . . . . .
C12 C 0.4592(2) 0.2657(2) 0.73341(18) 0.0425(5) Uani 1 1 d . . . . .
H12 H 0.416030 0.244692 0.677416 0.051 Uiso 1 1 calc R . . . .
C13 C 0.5989(3) 0.0159(2) 0.8589(2) 0.0628(7) Uani 1 1 d . . . . .
H13A H 0.723018 -0.015845 0.874145 0.094 Uiso 1 1 calc GR . . . .
H13B H 0.573602 -0.012397 0.799187 0.094 Uiso 1 1 calc GR . . . .
H13C H 0.535622 -0.027041 0.925505 0.094 Uiso 1 1 calc GR . . . .
C14 C 0.3027(2) 0.6992(2) 0.75980(16) 0.0363(4) Uani 1 1 d . . . . .
C15 C 0.3732(2) 0.7478(2) 0.82495(18) 0.0423(5) Uani 1 1 d . . . . .
H15 H 0.483917 0.767950 0.813865 0.051 Uiso 1 1 calc R . . . .
C16 C 0.1159(2) 0.7216(2) 0.89892(16) 0.0376(5) Uani 1 1 d . . . . .
C17 C 0.1364(2) 0.68100(19) 0.80588(16) 0.0344(4) Uani 1 1 d . . . . .
C18 C 0.0056(2) 0.6312(2) 0.77942(17) 0.0396(5) Uani 1 1 d . . . . .
H18 H 0.015531 0.603159 0.716942 0.048 Uiso 1 1 calc R . . . .
C19 C -0.1375(2) 0.6241(2) 0.84684(18) 0.0457(5) Uani 1 1 d . . . . .
H19 H -0.226878 0.589951 0.830564 0.055 Uiso 1 1 calc R . . . .
C20 C -0.1546(2) 0.6659(2) 0.93841(18) 0.0464(5) Uani 1 1 d . . . . .
H20 H -0.255657 0.658955 0.982493 0.056 Uiso 1 1 calc R . . . .
C21 C -0.0305(2) 0.7171(2) 0.96768(17) 0.0429(5) Uani 1 1 d . . . . .
C22 C -0.0474(3) 0.7628(3) 1.06491(19) 0.0593(7) Uani 1 1 d . . . . .
H22A H 0.051474 0.709075 1.114094 0.089 Uiso 1 1 calc GR . . . .
H22B H -0.154151 0.745681 1.104825 0.089 Uiso 1 1 calc GR . . . .
H22C H -0.050820 0.863818 1.039721 0.089 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 C6 1.435(3) . ?
N1 C7 1.276(3) . ?
N2 C7 1.398(2) . ?
N2 C10 1.368(3) . ?
N2 C12 1.390(3) . ?
N3 C10 1.309(2) . ?
N3 C11 1.393(3) . ?
N4 N5 1.224(2) . ?
N4 C8 1.495(2) . ?
N5 N6 1.133(3) . ?
N7 H7 0.902(17) . ?
N7 C15 1.377(3) . ?
N7 C16 1.386(3) . ?
C1 C2 1.400(4) . ?
C1 C6 1.387(3) . ?
C1 C9 1.493(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.380(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.399(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.382(3) . ?
C5 C6 1.389(3) . ?
C5 C8 1.516(3) . ?
C7 C8 1.546(3) . ?
C8 C14 1.500(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10 0.9500 . ?
C11 C12 1.347(3) . ?
C11 C13 1.486(3) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.360(3) . ?
C14 C17 1.439(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.405(3) . ?
C16 C21 1.407(3) . ?
C17 C18 1.403(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.377(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.395(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.384(3) . ?
C21 C22 1.491(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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 C6 106.04(18) . . ?
C10 N2 C7 128.47(18) . . ?
C10 N2 C12 106.09(17) . . ?
C12 N2 C7 125.41(18) . . ?
C10 N3 C11 105.43(17) . . ?
N5 N4 C8 116.28(17) . . ?
N6 N5 N4 172.1(2) . . ?
C15 N7 H7 124.9(18) . . ?
C15 N7 C16 107.71(18) . . ?
C16 N7 H7 125.4(18) . . ?
C2 C1 C9 122.0(2) . . ?
C6 C1 C2 115.5(3) . . ?
C6 C1 C9 122.5(2) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 C1 122.1(2) . . ?
C3 C2 H2 119.0 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.7(2) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 121.8 . . ?
C5 C4 C3 116.5(3) . . ?
C5 C4 H4 121.8 . . ?
C4 C5 C6 121.5(2) . . ?
C4 C5 C8 130.2(2) . . ?
C6 C5 C8 108.31(18) . . ?
C1 C6 N1 125.5(2) . . ?
C1 C6 C5 122.7(2) . . ?
C5 C6 N1 111.80(18) . . ?
N1 C7 N2 121.96(19) . . ?
N1 C7 C8 116.24(17) . . ?
N2 C7 C8 121.78(17) . . ?
N4 C8 C5 114.98(16) . . ?
N4 C8 C7 108.27(15) . . ?
N4 C8 C14 106.99(17) . . ?
C5 C8 C7 97.58(17) . . ?
C14 C8 C5 114.78(16) . . ?
C14 C8 C7 114.07(16) . . ?
C1 C9 H9A 109.5 . . ?
C1 C9 H9B 109.5 . . ?
C1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 H10 124.0 . . ?
N3 C10 N2 111.95(19) . . ?
N3 C10 H10 124.0 . . ?
N3 C11 C13 121.8(2) . . ?
C12 C11 N3 110.08(18) . . ?
C12 C11 C13 128.1(2) . . ?
N2 C12 H12 126.8 . . ?
C11 C12 N2 106.4(2) . . ?
C11 C12 H12 126.8 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C8 126.58(17) . . ?
C15 C14 C17 106.85(18) . . ?
C17 C14 C8 126.57(17) . . ?
N7 C15 H15 124.7 . . ?
C14 C15 N7 110.61(17) . . ?
C14 C15 H15 124.7 . . ?
N7 C16 C17 108.36(16) . . ?
N7 C16 C21 127.9(2) . . ?
C17 C16 C21 123.76(18) . . ?
C16 C17 C14 106.46(16) . . ?
C18 C17 C14 134.48(19) . . ?
C18 C17 C16 119.03(17) . . ?
C17 C18 H18 121.0 . . ?
C19 C18 C17 117.9(2) . . ?
C19 C18 H18 121.0 . . ?
C18 C19 H19 119.1 . . ?
C18 C19 C20 121.75(19) . . ?
C20 C19 H19 119.1 . . ?
C19 C20 H20 118.6 . . ?
C21 C20 C19 122.73(19) . . ?
C21 C20 H20 118.6 . . ?
C16 C21 C22 121.9(2) . . ?
C20 C21 C16 114.8(2) . . ?
C20 C21 C22 123.32(19) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C7 C8 N4 -119.58(18) . . . . ?
N1 C7 C8 C5 -0.1(2) . . . . ?
N1 C7 C8 C14 121.44(19) . . . . ?
N2 C7 C8 N4 58.6(2) . . . . ?
N2 C7 C8 C5 178.16(16) . . . . ?
N2 C7 C8 C14 -60.3(2) . . . . ?
N3 C11 C12 N2 0.3(2) . . . . ?
N4 C8 C14 C15 13.6(3) . . . . ?
N4 C8 C14 C17 -166.61(17) . . . . ?
N5 N4 C8 C5 -13.1(3) . . . . ?
N5 N4 C8 C7 94.8(2) . . . . ?
N5 N4 C8 C14 -141.9(2) . . . . ?
N7 C16 C17 C14 0.4(2) . . . . ?
N7 C16 C17 C18 178.73(16) . . . . ?
N7 C16 C21 C20 -178.08(18) . . . . ?
N7 C16 C21 C22 1.3(3) . . . . ?
C1 C2 C3 C4 -1.1(4) . . . . ?
C2 C1 C6 N1 -179.84(18) . . . . ?
C2 C1 C6 C5 1.4(3) . . . . ?
C2 C3 C4 C5 1.2(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C3 C4 C5 C8 -178.5(2) . . . . ?
C4 C5 C6 N1 179.78(17) . . . . ?
C4 C5 C6 C1 -1.3(3) . . . . ?
C4 C5 C8 N4 -66.2(3) . . . . ?
C4 C5 C8 C7 179.5(2) . . . . ?
C4 C5 C8 C14 58.5(3) . . . . ?
C5 C8 C14 C15 -115.2(2) . . . . ?
C5 C8 C14 C17 64.5(3) . . . . ?
C6 N1 C7 N2 -178.99(16) . . . . ?
C6 N1 C7 C8 -0.8(2) . . . . ?
C6 C1 C2 C3 -0.2(3) . . . . ?
C6 C5 C8 N4 115.17(19) . . . . ?
C6 C5 C8 C7 0.90(19) . . . . ?
C6 C5 C8 C14 -120.08(19) . . . . ?
C7 N1 C6 C1 -177.46(19) . . . . ?
C7 N1 C6 C5 1.4(2) . . . . ?
C7 N2 C10 N3 -177.55(17) . . . . ?
C7 N2 C12 C11 177.62(16) . . . . ?
C7 C8 C14 C15 133.3(2) . . . . ?
C7 C8 C14 C17 -46.9(2) . . . . ?
C8 C5 C6 N1 -1.5(2) . . . . ?
C8 C5 C6 C1 177.43(17) . . . . ?
C8 C14 C15 N7 179.05(18) . . . . ?
C8 C14 C17 C16 -179.57(17) . . . . ?
C8 C14 C17 C18 2.4(3) . . . . ?
C9 C1 C2 C3 -179.7(2) . . . . ?
C9 C1 C6 N1 -0.4(3) . . . . ?
C9 C1 C6 C5 -179.15(19) . . . . ?
C10 N2 C7 N1 -176.38(18) . . . . ?
C10 N2 C7 C8 5.5(3) . . . . ?
C10 N2 C12 C11 -0.4(2) . . . . ?
C10 N3 C11 C12 -0.1(2) . . . . ?
C10 N3 C11 C13 177.84(19) . . . . ?
C11 N3 C10 N2 -0.2(2) . . . . ?
C12 N2 C7 N1 6.0(3) . . . . ?
C12 N2 C7 C8 -172.12(16) . . . . ?
C12 N2 C10 N3 0.4(2) . . . . ?
C13 C11 C12 N2 -177.4(2) . . . . ?
C14 C17 C18 C19 177.61(19) . . . . ?
C15 N7 C16 C17 -0.8(2) . . . . ?
C15 N7 C16 C21 178.67(19) . . . . ?
C15 C14 C17 C16 0.2(2) . . . . ?
C15 C14 C17 C18 -177.8(2) . . . . ?
C16 N7 C15 C14 1.0(2) . . . . ?
C16 C17 C18 C19 -0.2(3) . . . . ?
C17 C14 C15 N7 -0.7(2) . . . . ?
C17 C16 C21 C20 1.3(3) . . . . ?
C17 C16 C21 C22 -179.30(18) . . . . ?
C17 C18 C19 C20 0.5(3) . . . . ?
C18 C19 C20 C21 0.1(3) . . . . ?
C19 C20 C21 C16 -1.0(3) . . . . ?
C19 C20 C21 C22 179.7(2) . . . . ?
C21 C16 C17 C14 -179.14(17) . . . . ?
C21 C16 C17 C18 -0.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/Hexyl hydride'
####################################################################### 
# 
# 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_y
_audit_block_doi                 10.5517/ccdc.csd.cc284vny
_database_code_depnum_ccdc_archive 'CCDC 2090040'
loop_
_audit_author_name
_audit_author_address
'Yi Jin'
;Yunnan University
China
;
_audit_update_record             
;
2021-08-24 deposited with the CCDC.	2021-08-25 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT026_y                   
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        31% Check
RESPONSE: This may be caused by the weak signal of the crystal cell.
;
# Added during the CSD deposition process: Tuesday 24 August 2021 11:21 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H31 N8'
_chemical_formula_weight         695.79

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

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

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

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

_cell_length_a                   7.196(5)
_cell_length_b                   19.955(15)
_cell_length_c                   24.468(18)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.0500(10)
_cell_angle_gamma                90.000(5)
_cell_volume                     3514(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    920
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      18.65

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_F_000             1452
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18249
_diffrn_reflns_av_unetI/netI     0.2361
_diffrn_reflns_av_R_equivalents  0.1185
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.317
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measured_fraction_theta_full 0.947
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_Laue_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_point_group_measured_fraction_full 0.947
_reflns_number_total             6548
_reflns_number_gt                2035
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6548
_refine_ls_number_parameters     487
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1983
_refine_ls_R_factor_gt           0.0621
_refine_ls_wR_factor_ref         0.1289
_refine_ls_wR_factor_gt          0.0985
_refine_ls_goodness_of_fit_ref   0.757
_refine_ls_restrained_S_all      0.757
_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 -0.2947(4) -0.27829(14) 0.52915(12) 0.0406(8) Uani 1 1 d . . . . .
C1 C -0.6924(5) -0.20727(17) 0.24549(15) 0.0418(10) Uani 1 1 d . . . . .
N2 N -0.1717(5) -0.33632(15) 0.59814(14) 0.0508(9) Uani 1 1 d . . . . .
C2 C -0.5367(6) -0.24775(18) 0.26685(16) 0.0487(11) Uani 1 1 d . . . . .
N3 N -0.4361(4) -0.17818(14) 0.49682(13) 0.0480(9) Uani 1 1 d . . . . .
H3A H -0.523629 -0.178302 0.520741 0.058 Uiso 1 1 d R U . . .
C39 C 0.1539(8) -0.3387(3) 0.40247(18) 0.0698(15) Uani 1 1 d . . . . .
C38 C 0.2162(9) -0.4052(3) 0.3969(2) 0.099(2) Uani 1 1 d . . . . .
H38 H 0.330241 -0.414368 0.380643 0.119 Uiso 1 1 calc R U . . .
C37 C 0.1080(11) -0.4555(3) 0.4153(2) 0.108(2) Uani 1 1 d . . . . .
H37 H 0.149570 -0.499502 0.412475 0.130 Uiso 1 1 calc R U . . .
C36 C -0.0637(9) -0.4429(2) 0.4385(2) 0.091(2) Uani 1 1 d . . . . .
H7A H -0.136149 -0.478321 0.450927 0.109 Uiso 1 1 calc R U . . .
N7 N -0.7918(4) -0.27216(14) 0.16280(12) 0.0405(8) Uani 1 1 d . . . . .
C35 C -0.1285(7) -0.3777(2) 0.44331(17) 0.0656(14) Uani 1 1 d . . . . .
H35 H -0.246068 -0.369573 0.457653 0.079 Uiso 1 1 calc R U . . .
C34 C -0.0184(7) -0.3248(2) 0.42680(17) 0.0543(12) Uani 1 1 d . . . . .
C33 C -0.0360(7) -0.25306(19) 0.42703(17) 0.0500(11) Uani 1 1 d . . . . .
C32 C -0.1913(6) -0.21318(17) 0.44782(16) 0.0418(10) Uani 1 1 d . . . . .
C31 C -0.1456(6) -0.29097(18) 0.56139(16) 0.0466(11) Uani 1 1 d . . . . .
H31 H -0.032947 -0.268667 0.557325 0.056 Uiso 1 1 calc R U . . .
C30 C -0.3546(6) -0.35584(17) 0.59018(16) 0.0421(10) Uani 1 1 d . . . . .
C29 C -0.4603(7) -0.40119(18) 0.61873(18) 0.0568(12) Uani 1 1 d . . . . .
H29 H -0.411404 -0.424269 0.648470 0.068 Uiso 1 1 calc R U . . .
C28 C -0.6386(7) -0.4113(2) 0.60220(19) 0.0682(14) Uani 1 1 d . . . . .
H28 H -0.711878 -0.441874 0.621138 0.082 Uiso 1 1 calc R U . . .
C27 C -0.7140(7) -0.37771(19) 0.5582(2) 0.0684(14) Uani 1 1 d . . . . .
H27 H -0.834826 -0.387530 0.547381 0.082 Uiso 1 1 calc R U . . .
C26 C -0.6157(6) -0.33035(19) 0.53017(19) 0.0598(13) Uani 1 1 d . . . . .
H26 H -0.667344 -0.306078 0.501487 0.072 Uiso 1 1 calc R U . . .
C25 C -0.4338(5) -0.32082(16) 0.54725(16) 0.0410(10) Uani 1 1 d . . . . .
C3 C -0.3804(7) -0.2226(2) 0.28928(19) 0.0683(15) Uani 1 1 d . . . . .
H3 H -0.353361 -0.177227 0.292829 0.082 Uiso 1 1 calc R U . . .
C9 C -0.5221(6) -0.3191(2) 0.26934(16) 0.0462(11) Uani 1 1 d . . . . .
C7 C -0.5732(7) -0.4364(2) 0.26223(18) 0.0660(14) Uani 1 1 d . . . . .
H7 H -0.648100 -0.472133 0.251679 0.079 Uiso 1 1 calc R U . . .
C4 C -0.3527(7) -0.3336(2) 0.29459(17) 0.0598(13) Uani 1 1 d . . . . .
C5 C -0.2898(7) -0.3985(2) 0.30281(18) 0.0728(15) Uani 1 1 d . . . . .
H5 H -0.175280 -0.407084 0.319011 0.087 Uiso 1 1 calc R U . . .
C6 C -0.4031(8) -0.4491(2) 0.28612(19) 0.0702(14) Uani 1 1 d . . . . .
H6 H -0.365063 -0.493287 0.290925 0.084 Uiso 1 1 calc R U . . .
C8 C -0.6340(6) -0.3721(2) 0.25374(16) 0.0565(12) Uani 1 1 d . . . . .
H8 H -0.749117 -0.364219 0.237683 0.068 Uiso 1 1 calc R U . . .
C10 C -0.8044(6) -0.22096(17) 0.20174(15) 0.0427(10) Uani 1 1 d . . . . .
C11 C -0.6423(6) -0.28392(19) 0.13130(16) 0.0482(11) Uani 1 1 d . . . . .
H11 H -0.529840 -0.261718 0.136031 0.058 Uiso 1 1 calc R U . . .
C12 C -0.8527(6) -0.34855(18) 0.10034(16) 0.0443(11) Uani 1 1 d . . . . .
C13 C -0.9570(6) -0.39390(18) 0.06961(18) 0.0554(12) Uani 1 1 d . . . . .
H13 H -0.907564 -0.416254 0.039606 0.066 Uiso 1 1 calc R U . . .
C14 C -1.1376(7) -0.4035(2) 0.0864(2) 0.0624(14) Uani 1 1 d . . . . .
H14 H -1.212573 -0.433081 0.066993 0.075 Uiso 1 1 calc R U . . .
C15 C -1.2109(6) -0.37083(19) 0.1310(2) 0.0596(13) Uani 1 1 d . . . . .
H15 H -1.332756 -0.380007 0.141249 0.072 Uiso 1 1 calc R U . . .
C16 C -1.1105(6) -0.32508(18) 0.16109(17) 0.0516(11) Uani 1 1 d . . . . .
H16 H -1.160761 -0.302809 0.191024 0.062 Uiso 1 1 calc R U . . .
C17 C -0.9286(5) -0.31436(17) 0.14366(16) 0.0396(10) Uani 1 1 d . . . . .
C18 C -0.9044(6) -0.12403(18) 0.23236(16) 0.0448(10) Uani 1 1 d . . . . .
C19 C -0.9985(6) -0.06390(19) 0.24015(16) 0.0540(12) Uani 1 1 d . . . . .
H19 H -1.097926 -0.051506 0.218049 0.065 Uiso 1 1 calc R U . . .
C21 C -0.7931(7) -0.04370(19) 0.31576(16) 0.0570(12) Uani 1 1 d . . . . .
H21 H -0.756798 -0.015814 0.344297 0.068 Uiso 1 1 calc R U . . .
C22 C -0.7014(6) -0.10364(19) 0.30832(16) 0.0525(11) Uani 1 1 d . . . . .
H22 H -0.604748 -0.116332 0.331341 0.063 Uiso 1 1 calc R U . . .
C23 C -0.7576(5) -0.14450(17) 0.26553(15) 0.0418(10) Uani 1 1 d . . . . .
C24 C -0.3069(6) -0.22655(17) 0.49004(15) 0.0398(10) Uani 1 1 d . . . . .
N4 N 0.2401(6) -0.2794(2) 0.38856(15) 0.0794(13) Uani 1 1 d . . . . .
N5 N -0.6686(5) -0.32928(15) 0.09337(13) 0.0502(9) Uani 1 1 d . . . . .
N6 N -0.9352(4) -0.17227(14) 0.19366(13) 0.0462(9) Uani 1 1 d . . . . .
H6A H -1.020157 -0.172052 0.168949 0.055 Uiso 1 1 d R U . . .
C46 C -0.4037(6) -0.12910(18) 0.45955(16) 0.0415(10) Uani 1 1 d . . . . .
C45 C -0.4935(6) -0.06790(17) 0.45339(17) 0.0523(11) Uani 1 1 d . . . . .
H45 H -0.595255 -0.056296 0.474781 0.063 Uiso 1 1 calc R U . . .
C44 C -0.4251(7) -0.0257(2) 0.41448(18) 0.0596(13) Uani 1 1 d . . . . .
H44 H -0.478652 0.016353 0.410018 0.072 Uiso 1 1 calc R U . . .
C43 C -0.2799(7) -0.04395(19) 0.38199(17) 0.0571(13) Uani 1 1 d . . . . .
H43 H -0.239605 -0.014365 0.355124 0.069 Uiso 1 1 calc R U . . .
C42 C -0.1904(6) -0.10495(18) 0.38758(16) 0.0525(11) Uani 1 1 d . . . . .
H42 H -0.091632 -0.116477 0.364955 0.063 Uiso 1 1 calc R U . . .
C41 C -0.2522(6) -0.14842(18) 0.42791(16) 0.0442(11) Uani 1 1 d . . . . .
C40 C 0.1219(7) -0.2290(2) 0.40384(18) 0.0648(13) Uani 1 1 d . . . . .
H40 H 0.146723 -0.183662 0.398915 0.078 Uiso 1 1 calc R U . . .
N8 N -0.2675(5) -0.27377(18) 0.30602(16) 0.0741(13) Uani 1 1 d . . . . .
H20A H -0.160241 -0.269139 0.321038 0.089 Uiso 1 1 d R U . . .
C20 C -0.9375(6) -0.02371(18) 0.28204(18) 0.0566(12) Uani 1 1 d . . . . .
H20 H -0.994132 0.017575 0.287869 0.068 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C31 1.355(4) . ?
N1 C25 1.385(5) . ?
N1 C24 1.410(4) . ?
C1 C10 1.367(4) . ?
C1 C23 1.425(5) . ?
C1 C2 1.476(5) . ?
N2 C31 1.289(4) . ?
N2 C30 1.386(5) . ?
C2 C3 1.348(5) . ?
C2 C9 1.428(5) . ?
N3 C24 1.350(4) . ?
N3 C46 1.359(4) . ?
N3 H3A 0.8603 . ?
C39 N4 1.379(6) . ?
C39 C34 1.404(7) . ?
C39 C38 1.408(6) . ?
C38 C37 1.349(8) . ?
C38 H38 0.9300 . ?
C37 C36 1.382(8) . ?
C37 H37 0.9300 . ?
C36 C35 1.388(5) . ?
C36 H7A 0.9300 . ?
N7 C11 1.345(5) . ?
N7 C17 1.377(4) . ?
N7 C10 1.400(4) . ?
C35 C34 1.380(6) . ?
C35 H35 0.9300 . ?
C34 C33 1.437(5) . ?
C33 C40 1.358(6) . ?
C33 C32 1.464(6) . ?
C32 C24 1.354(6) . ?
C32 C41 1.449(5) . ?
C31 H31 0.9300 . ?
C30 C29 1.373(5) . ?
C30 C25 1.384(4) . ?
C29 C28 1.360(5) . ?
C29 H29 0.9300 . ?
C28 C27 1.379(5) . ?
C28 H28 0.9300 . ?
C27 C26 1.366(6) . ?
C27 H27 0.9300 . ?
C26 C25 1.386(5) . ?
C26 H26 0.9300 . ?
C3 N8 1.367(4) . ?
C3 H3 0.9300 . ?
C9 C8 1.383(5) . ?
C9 C4 1.396(5) . ?
C7 C8 1.372(5) . ?
C7 C6 1.379(5) . ?
C7 H7 0.9300 . ?
C4 N8 1.371(5) . ?
C4 C5 1.387(5) . ?
C5 C6 1.361(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 H8 0.9300 . ?
C10 N6 1.367(4) . ?
C11 N5 1.310(4) . ?
C11 H11 0.9300 . ?
C12 C17 1.374(5) . ?
C12 N5 1.391(5) . ?
C12 C13 1.395(5) . ?
C13 C14 1.377(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.377(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.377(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.394(6) . ?
C16 H16 0.9300 . ?
C18 N6 1.368(4) . ?
C18 C19 1.391(5) . ?
C18 C23 1.393(4) . ?
C19 C20 1.373(5) . ?
C19 H19 0.9300 . ?
C21 C22 1.378(5) . ?
C21 C20 1.385(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.387(4) . ?
C22 H22 0.9300 . ?
N4 C40 1.370(5) . ?
N6 H6A 0.8596 . ?
C46 C45 1.390(5) . ?
C46 C41 1.392(6) . ?
C45 C44 1.363(6) . ?
C45 H45 0.9300 . ?
C44 C43 1.363(6) . ?
C44 H44 0.9300 . ?
C43 C42 1.384(5) . ?
C43 H43 0.9300 . ?
C42 C41 1.388(5) . ?
C42 H42 0.9300 . ?
C40 H40 0.9300 . ?
N8 H20A 0.8598 . ?
C20 H20 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C31 N1 C25 105.8(3) . . ?
C31 N1 C24 125.5(3) . . ?
C25 N1 C24 128.3(3) . . ?
C10 C1 C23 104.5(3) . . ?
C10 C1 C2 127.9(3) . . ?
C23 C1 C2 127.5(3) . . ?
C31 N2 C30 103.8(3) . . ?
C3 C2 C9 107.0(3) . . ?
C3 C2 C1 125.0(4) . . ?
C9 C2 C1 128.0(3) . . ?
C24 N3 C46 108.3(3) . . ?
C24 N3 H3A 125.9 . . ?
C46 N3 H3A 125.8 . . ?
N4 C39 C34 109.4(4) . . ?
N4 C39 C38 129.9(6) . . ?
C34 C39 C38 120.6(6) . . ?
C37 C38 C39 119.0(6) . . ?
C37 C38 H38 120.5 . . ?
C39 C38 H38 120.5 . . ?
C38 C37 C36 121.2(6) . . ?
C38 C37 H37 119.4 . . ?
C36 C37 H37 119.4 . . ?
C37 C36 C35 120.4(6) . . ?
C37 C36 H7A 119.8 . . ?
C35 C36 H7A 119.8 . . ?
C11 N7 C17 105.7(3) . . ?
C11 N7 C10 124.7(3) . . ?
C17 N7 C10 129.2(3) . . ?
C34 C35 C36 119.9(5) . . ?
C34 C35 H35 120.0 . . ?
C36 C35 H35 120.0 . . ?
C35 C34 C39 118.7(5) . . ?
C35 C34 C33 135.2(5) . . ?
C39 C34 C33 106.0(5) . . ?
C40 C33 C34 106.1(4) . . ?
C40 C33 C32 126.3(4) . . ?
C34 C33 C32 127.6(5) . . ?
C24 C32 C41 104.3(4) . . ?
C24 C32 C33 128.9(4) . . ?
C41 C32 C33 126.8(4) . . ?
N2 C31 N1 114.9(4) . . ?
N2 C31 H31 122.6 . . ?
N1 C31 H31 122.6 . . ?
C29 C30 C25 119.4(4) . . ?
C29 C30 N2 129.8(4) . . ?
C25 C30 N2 110.8(4) . . ?
C28 C29 C30 118.0(4) . . ?
C28 C29 H29 121.0 . . ?
C30 C29 H29 121.0 . . ?
C29 C28 C27 122.0(4) . . ?
C29 C28 H28 119.0 . . ?
C27 C28 H28 119.0 . . ?
C26 C27 C28 121.7(4) . . ?
C26 C27 H27 119.2 . . ?
C28 C27 H27 119.2 . . ?
C27 C26 C25 115.6(4) . . ?
C27 C26 H26 122.2 . . ?
C25 C26 H26 122.2 . . ?
C30 C25 N1 104.7(3) . . ?
C30 C25 C26 123.2(4) . . ?
N1 C25 C26 132.1(4) . . ?
C2 C3 N8 109.8(4) . . ?
C2 C3 H3 125.1 . . ?
N8 C3 H3 125.1 . . ?
C8 C9 C4 118.1(4) . . ?
C8 C9 C2 135.0(4) . . ?
C4 C9 C2 106.9(3) . . ?
C8 C7 C6 121.3(4) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
N8 C4 C5 129.7(4) . . ?
N8 C4 C9 107.4(4) . . ?
C5 C4 C9 122.9(4) . . ?
C6 C5 C4 117.0(4) . . ?
C6 C5 H5 121.5 . . ?
C4 C5 H5 121.5 . . ?
C5 C6 C7 121.5(4) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C7 C8 C9 119.2(4) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
N6 C10 C1 112.1(3) . . ?
N6 C10 N7 117.7(3) . . ?
C1 C10 N7 129.8(3) . . ?
N5 C11 N7 114.3(3) . . ?
N5 C11 H11 122.8 . . ?
N7 C11 H11 122.8 . . ?
C17 C12 N5 109.7(3) . . ?
C17 C12 C13 121.6(4) . . ?
N5 C12 C13 128.7(4) . . ?
C14 C13 C12 115.9(5) . . ?
C14 C13 H13 122.1 . . ?
C12 C13 H13 122.1 . . ?
C13 C14 C15 122.2(4) . . ?
C13 C14 H14 118.9 . . ?
C15 C14 H14 118.9 . . ?
C16 C15 C14 122.4(5) . . ?
C16 C15 H15 118.8 . . ?
C14 C15 H15 118.8 . . ?
C15 C16 C17 115.5(4) . . ?
C15 C16 H16 122.2 . . ?
C17 C16 H16 122.2 . . ?
C12 C17 N7 106.4(4) . . ?
C12 C17 C16 122.2(4) . . ?
N7 C17 C16 131.4(4) . . ?
N6 C18 C19 128.6(3) . . ?
N6 C18 C23 108.6(3) . . ?
C19 C18 C23 122.8(4) . . ?
C20 C19 C18 116.8(4) . . ?
C20 C19 H19 121.6 . . ?
C18 C19 H19 121.6 . . ?
C22 C21 C20 122.0(4) . . ?
C22 C21 H21 119.0 . . ?
C20 C21 H21 119.0 . . ?
C21 C22 C23 118.1(4) . . ?
C21 C22 H22 120.9 . . ?
C23 C22 H22 120.9 . . ?
C22 C23 C18 119.2(4) . . ?
C22 C23 C1 132.9(4) . . ?
C18 C23 C1 107.9(3) . . ?
N3 C24 C32 112.1(3) . . ?
N3 C24 N1 118.9(4) . . ?
C32 C24 N1 128.6(4) . . ?
C40 N4 C39 106.4(4) . . ?
C11 N5 C12 103.9(4) . . ?
C10 N6 C18 106.8(3) . . ?
C10 N6 H6A 126.5 . . ?
C18 N6 H6A 126.7 . . ?
N3 C46 C45 128.8(4) . . ?
N3 C46 C41 108.0(3) . . ?
C45 C46 C41 123.2(4) . . ?
C44 C45 C46 116.8(5) . . ?
C44 C45 H45 121.6 . . ?
C46 C45 H45 121.6 . . ?
C45 C44 C43 121.3(4) . . ?
C45 C44 H44 119.3 . . ?
C43 C44 H44 119.3 . . ?
C44 C43 C42 122.3(4) . . ?
C44 C43 H43 118.9 . . ?
C42 C43 H43 118.9 . . ?
C43 C42 C41 118.1(5) . . ?
C43 C42 H42 121.0 . . ?
C41 C42 H42 121.0 . . ?
C42 C41 C46 118.3(4) . . ?
C42 C41 C32 134.4(4) . . ?
C46 C41 C32 107.3(4) . . ?
C33 C40 N4 112.0(4) . . ?
C33 C40 H40 124.0 . . ?
N4 C40 H40 124.0 . . ?
C3 N8 C4 108.9(3) . . ?
C3 N8 H20A 125.5 . . ?
C4 N8 H20A 125.6 . . ?
C19 C20 C21 121.0(4) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?

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
C10 C1 C2 C3 145.4(5) . . . . ?
C23 C1 C2 C3 -33.5(7) . . . . ?
C10 C1 C2 C9 -36.3(7) . . . . ?
C23 C1 C2 C9 144.8(5) . . . . ?
N4 C39 C38 C37 177.8(5) . . . . ?
C34 C39 C38 C37 -0.2(7) . . . . ?
C39 C38 C37 C36 1.4(9) . . . . ?
C38 C37 C36 C35 -0.1(9) . . . . ?
C37 C36 C35 C34 -2.4(7) . . . . ?
C36 C35 C34 C39 3.6(6) . . . . ?
C36 C35 C34 C33 -177.9(4) . . . . ?
N4 C39 C34 C35 179.3(3) . . . . ?
C38 C39 C34 C35 -2.3(6) . . . . ?
N4 C39 C34 C33 0.4(5) . . . . ?
C38 C39 C34 C33 178.7(4) . . . . ?
C35 C34 C33 C40 -179.0(4) . . . . ?
C39 C34 C33 C40 -0.3(5) . . . . ?
C35 C34 C33 C32 1.0(7) . . . . ?
C39 C34 C33 C32 179.7(4) . . . . ?
C40 C33 C32 C24 -148.0(4) . . . . ?
C34 C33 C32 C24 32.0(6) . . . . ?
C40 C33 C32 C41 30.2(6) . . . . ?
C34 C33 C32 C41 -149.8(4) . . . . ?
C30 N2 C31 N1 -0.2(4) . . . . ?
C25 N1 C31 N2 -0.2(4) . . . . ?
C24 N1 C31 N2 173.1(4) . . . . ?
C31 N2 C30 C29 -177.6(4) . . . . ?
C31 N2 C30 C25 0.5(4) . . . . ?
C25 C30 C29 C28 2.1(6) . . . . ?
N2 C30 C29 C28 -179.9(4) . . . . ?
C30 C29 C28 C27 0.0(7) . . . . ?
C29 C28 C27 C26 -2.6(8) . . . . ?
C28 C27 C26 C25 2.9(7) . . . . ?
C29 C30 C25 N1 177.7(4) . . . . ?
N2 C30 C25 N1 -0.7(4) . . . . ?
C29 C30 C25 C26 -1.8(6) . . . . ?
N2 C30 C25 C26 179.8(4) . . . . ?
C31 N1 C25 C30 0.5(4) . . . . ?
C24 N1 C25 C30 -172.6(3) . . . . ?
C31 N1 C25 C26 179.9(4) . . . . ?
C24 N1 C25 C26 6.9(7) . . . . ?
C27 C26 C25 C30 -0.7(6) . . . . ?
C27 C26 C25 N1 180.0(4) . . . . ?
C9 C2 C3 N8 -0.2(6) . . . . ?
C1 C2 C3 N8 178.4(4) . . . . ?
C3 C2 C9 C8 179.6(5) . . . . ?
C1 C2 C9 C8 1.1(8) . . . . ?
C3 C2 C9 C4 0.7(5) . . . . ?
C1 C2 C9 C4 -177.9(4) . . . . ?
C8 C9 C4 N8 179.9(4) . . . . ?
C2 C9 C4 N8 -0.9(5) . . . . ?
C8 C9 C4 C5 2.4(7) . . . . ?
C2 C9 C4 C5 -178.5(5) . . . . ?
N8 C4 C5 C6 -178.4(5) . . . . ?
C9 C4 C5 C6 -1.4(8) . . . . ?
C4 C5 C6 C7 -0.2(8) . . . . ?
C8 C7 C6 C5 0.8(8) . . . . ?
C6 C7 C8 C9 0.2(7) . . . . ?
C4 C9 C8 C7 -1.7(7) . . . . ?
C2 C9 C8 C7 179.5(5) . . . . ?
C23 C1 C10 N6 -0.9(5) . . . . ?
C2 C1 C10 N6 179.9(4) . . . . ?
C23 C1 C10 N7 172.2(4) . . . . ?
C2 C1 C10 N7 -7.0(7) . . . . ?
C11 N7 C10 N6 116.7(4) . . . . ?
C17 N7 C10 N6 -54.4(5) . . . . ?
C11 N7 C10 C1 -56.1(6) . . . . ?
C17 N7 C10 C1 132.8(4) . . . . ?
C17 N7 C11 N5 0.4(5) . . . . ?
C10 N7 C11 N5 -172.5(3) . . . . ?
C17 C12 C13 C14 -1.9(6) . . . . ?
N5 C12 C13 C14 179.6(4) . . . . ?
C12 C13 C14 C15 -0.4(6) . . . . ?
C13 C14 C15 C16 1.7(7) . . . . ?
C14 C15 C16 C17 -0.5(6) . . . . ?
N5 C12 C17 N7 1.6(4) . . . . ?
C13 C12 C17 N7 -177.2(3) . . . . ?
N5 C12 C17 C16 -178.1(3) . . . . ?
C13 C12 C17 C16 3.1(6) . . . . ?
C11 N7 C17 C12 -1.2(4) . . . . ?
C10 N7 C17 C12 171.2(3) . . . . ?
C11 N7 C17 C16 178.5(4) . . . . ?
C10 N7 C17 C16 -9.1(6) . . . . ?
C15 C16 C17 C12 -1.8(6) . . . . ?
C15 C16 C17 N7 178.6(3) . . . . ?
N6 C18 C19 C20 -179.2(4) . . . . ?
C23 C18 C19 C20 1.4(6) . . . . ?
C20 C21 C22 C23 0.0(6) . . . . ?
C21 C22 C23 C18 -0.7(6) . . . . ?
C21 C22 C23 C1 178.0(4) . . . . ?
N6 C18 C23 C22 -179.5(4) . . . . ?
C19 C18 C23 C22 0.0(6) . . . . ?
N6 C18 C23 C1 1.5(4) . . . . ?
C19 C18 C23 C1 -179.0(4) . . . . ?
C10 C1 C23 C22 -179.2(4) . . . . ?
C2 C1 C23 C22 0.0(7) . . . . ?
C10 C1 C23 C18 -0.3(4) . . . . ?
C2 C1 C23 C18 178.8(4) . . . . ?
C46 N3 C24 C32 -2.3(4) . . . . ?
C46 N3 C24 N1 170.8(3) . . . . ?
C41 C32 C24 N3 2.3(4) . . . . ?
C33 C32 C24 N3 -179.3(3) . . . . ?
C41 C32 C24 N1 -170.1(3) . . . . ?
C33 C32 C24 N1 8.4(7) . . . . ?
C31 N1 C24 N3 -117.2(4) . . . . ?
C25 N1 C24 N3 54.5(5) . . . . ?
C31 N1 C24 C32 54.6(6) . . . . ?
C25 N1 C24 C32 -133.6(4) . . . . ?
C34 C39 N4 C40 -0.3(5) . . . . ?
C38 C39 N4 C40 -178.5(4) . . . . ?
N7 C11 N5 C12 0.6(4) . . . . ?
C17 C12 N5 C11 -1.4(4) . . . . ?
C13 C12 N5 C11 177.3(4) . . . . ?
C1 C10 N6 C18 1.9(5) . . . . ?
N7 C10 N6 C18 -172.2(3) . . . . ?
C19 C18 N6 C10 178.5(4) . . . . ?
C23 C18 N6 C10 -2.0(4) . . . . ?
C24 N3 C46 C45 -175.7(3) . . . . ?
C24 N3 C46 C41 1.3(4) . . . . ?
N3 C46 C45 C44 175.9(4) . . . . ?
C41 C46 C45 C44 -0.7(6) . . . . ?
C46 C45 C44 C43 2.3(6) . . . . ?
C45 C44 C43 C42 -2.0(7) . . . . ?
C44 C43 C42 C41 -0.1(6) . . . . ?
C43 C42 C41 C46 1.7(5) . . . . ?
C43 C42 C41 C32 -176.4(4) . . . . ?
N3 C46 C41 C42 -178.5(3) . . . . ?
C45 C46 C41 C42 -1.3(6) . . . . ?
N3 C46 C41 C32 0.0(4) . . . . ?
C45 C46 C41 C32 177.2(3) . . . . ?
C24 C32 C41 C42 176.8(4) . . . . ?
C33 C32 C41 C42 -1.7(7) . . . . ?
C24 C32 C41 C46 -1.4(4) . . . . ?
C33 C32 C41 C46 -179.9(3) . . . . ?
C34 C33 C40 N4 0.1(5) . . . . ?
C32 C33 C40 N4 -179.9(3) . . . . ?
C39 N4 C40 C33 0.2(5) . . . . ?
C2 C3 N8 C4 -0.4(6) . . . . ?
C5 C4 N8 C3 178.2(5) . . . . ?
C9 C4 N8 C3 0.8(5) . . . . ?
C18 C19 C20 C21 -2.1(6) . . . . ?
C22 C21 C20 C19 1.4(7) . . . . ?

_refine_diff_density_max         0.164
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.042

