# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_d8v19821_0m
_database_code_depnum_ccdc_archive 'CCDC 2157126'
loop_
_audit_author_name
_audit_author_address
'Yipu Wang'
;East China University of Science and Technology
China
;
_audit_update_record             
;
2022-03-08 deposited with the CCDC.	2022-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H16 N2 O2'
_chemical_formula_weight         328.36

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      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_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+1/2'

_cell_length_a                   3.7948(18)
_cell_length_b                   17.822(8)
_cell_length_c                   12.105(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.084(16)
_cell_angle_gamma                90
_cell_volume                     816.6(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1345
_cell_measurement_theta_min      5.657
_cell_measurement_theta_max      42.233

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5032
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            7311
_diffrn_reflns_av_unetI/netI     0.1245
_diffrn_reflns_av_R_equivalents  0.1268
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.286
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measured_fraction_theta_full 0.901
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_Laue_measured_fraction_full 0.901
_diffrn_reflns_point_group_measured_fraction_max 0.859
_diffrn_reflns_point_group_measured_fraction_full 0.835
_reflns_number_total             2483
_reflns_number_gt                1221
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.839
_reflns_Friedel_fraction_max     0.790
_reflns_Friedel_fraction_full    0.767

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0711P)²+0.0378P] 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     SHELXL
_refine_ls_extinction_coef       0.018(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 414 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.4(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2483
_refine_ls_number_parameters     230
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1676
_refine_ls_R_factor_gt           0.0708
_refine_ls_wR_factor_ref         0.1887
_refine_ls_wR_factor_gt          0.1400
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.006
_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
O1 O 0.848(3) 0.8816(4) 0.5829(8) 0.092(3) Uani 1 1 d . . . . .
N1 N 0.271(3) 0.0123(5) 0.3715(9) 0.080(4) Uani 1 1 d . . . . .
N2 N 1.023(3) 0.4894(4) 0.7385(9) 0.072(4) Uani 1 1 d . . . . .
C1 C 0.678(4) 0.8484(5) 0.5093(12) 0.069(5) Uani 1 1 d . . . . .
H1 H 0.5576 0.8759 0.4533 0.082 Uiso 1 1 calc R U . . .
C2 C 0.657(4) 0.7654(5) 0.5062(10) 0.054(3) Uani 1 1 d . . . . .
C3 C 0.802(3) 0.7228(6) 0.5936(10) 0.058(3) Uani 1 1 d . . . . .
H3 H 0.9098 0.7464 0.6557 0.070 Uiso 1 1 calc R U . . .
C4 C 0.786(3) 0.6449(5) 0.5890(9) 0.055(3) Uani 1 1 d . . . . .
H4 H 0.8892 0.6166 0.6472 0.066 Uiso 1 1 calc R U . . .
C5 C 0.617(3) 0.6089(5) 0.4972(9) 0.048(3) Uani 1 1 d . . . . .
C6 C 0.479(3) 0.6522(5) 0.4118(9) 0.051(3) Uani 1 1 d . . . . .
H6 H 0.3724 0.6289 0.3493 0.062 Uiso 1 1 calc R U . . .
C7 C 0.493(3) 0.7312(6) 0.4156(10) 0.054(3) Uani 1 1 d . . . . .
H7 H 0.3920 0.7597 0.3572 0.065 Uiso 1 1 calc R U . . .
C8 C 0.579(3) 0.5286(5) 0.4826(8) 0.044(3) Uani 1 1 d . . . . .
H8 H 0.4558 0.5147 0.4167 0.052 Uiso 1 1 calc R U . . .
C9 C 0.687(3) 0.4714(5) 0.5458(9) 0.044(3) Uani 1 1 d . . . . .
C10 C 0.871(4) 0.4827(5) 0.6527(12) 0.055(3) Uani 1 1 d . . . . .
C11 C 0.620(3) 0.3915(5) 0.5174(8) 0.041(3) Uani 1 1 d . . . . .
C12 C 0.689(3) 0.3353(5) 0.5946(9) 0.052(3) Uani 1 1 d . . . . .
H12 H 0.7809 0.3470 0.6658 0.062 Uiso 1 1 calc R U . . .
C13 C 0.620(4) 0.2607(6) 0.5650(10) 0.061(4) Uani 1 1 d . . . . .
H13 H 0.6618 0.2235 0.6182 0.073 Uiso 1 1 calc R U . . .
C14 C 0.494(3) 0.2402(5) 0.4609(10) 0.050(3) Uani 1 1 d . . . . .
C15 C 0.431(3) 0.2972(6) 0.3849(9) 0.057(3) Uani 1 1 d . . . . .
H15 H 0.3461 0.2853 0.3131 0.068 Uiso 1 1 calc R U . . .
C16 C 0.492(3) 0.3709(5) 0.4124(9) 0.057(4) Uani 1 1 d . . . . .
H16 H 0.4465 0.4078 0.3590 0.068 Uiso 1 1 calc R U . . .
C17 C 0.419(3) 0.1625(5) 0.4323(10) 0.054(3) Uani 1 1 d . . . . .
C18 C 0.301(3) 0.1102(5) 0.5070(9) 0.062(3) Uani 1 1 d . . . . .
H18 H 0.2705 0.1242 0.5798 0.074 Uiso 1 1 calc R U . . .
C19 C 0.230(4) 0.0382(5) 0.4727(10) 0.070(4) Uani 1 1 d . . . . .
H19 H 0.1472 0.0049 0.5240 0.084 Uiso 1 1 calc R U . . .
C20 C 0.391(4) 0.0614(6) 0.3008(11) 0.081(4) Uani 1 1 d . . . . .
H20 H 0.4311 0.0451 0.2298 0.097 Uiso 1 1 calc R U . . .
C21 C 0.459(3) 0.1345(5) 0.3274(9) 0.061(3) Uani 1 1 d . . . . .
H21 H 0.5344 0.1666 0.2733 0.073 Uiso 1 1 calc R U . . .
O2 O 0.990(4) 0.8830(5) 0.2665(11) 0.133(5) Uani 1 1 d G . . . .
H2A H 1.0906 0.9234 0.2886 0.199 Uiso 1 1 d G U . . .
H2B H 0.7685 0.8869 0.2708 0.199 Uiso 1 1 d G 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
O1 C1 1.216(14) . ?
N1 C20 1.326(13) . ?
N1 C19 1.328(13) . ?
N2 C10 1.157(16) . ?
C1 C2 1.482(12) . ?
C1 H1 0.9300 . ?
C2 C7 1.365(16) . ?
C2 C3 1.383(15) . ?
C3 C4 1.391(13) . ?
C3 H3 0.9300 . ?
C4 C5 1.400(14) . ?
C4 H4 0.9300 . ?
C5 C6 1.364(14) . ?
C5 C8 1.447(12) . ?
C6 C7 1.410(13) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.322(12) . ?
C8 H8 0.9300 . ?
C9 C10 1.440(18) . ?
C9 C11 1.483(12) . ?
C11 C16 1.378(15) . ?
C11 C12 1.383(12) . ?
C12 C13 1.396(15) . ?
C12 H12 0.9300 . ?
C13 C14 1.366(14) . ?
C13 H13 0.9300 . ?
C14 C15 1.379(13) . ?
C14 C17 1.452(13) . ?
C15 C16 1.371(13) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C21 1.382(14) . ?
C17 C18 1.393(13) . ?
C18 C19 1.371(13) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.363(13) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
O2 H2A 0.8499 . ?
O2 H2B 0.8500 . ?

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
C20 N1 C19 115.8(10) . . ?
O1 C1 C2 122.0(13) . . ?
O1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C7 C2 C3 120.3(10) . . ?
C7 C2 C1 119.1(12) . . ?
C3 C2 C1 120.6(11) . . ?
C2 C3 C4 120.2(11) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 120.4(11) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 118.1(9) . . ?
C6 C5 C8 116.0(10) . . ?
C4 C5 C8 125.9(10) . . ?
C5 C6 C7 121.9(10) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C2 C7 C6 119.1(12) . . ?
C2 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C9 C8 C5 131.9(10) . . ?
C9 C8 H8 114.1 . . ?
C5 C8 H8 114.1 . . ?
C8 C9 C10 121.5(9) . . ?
C8 C9 C11 124.4(10) . . ?
C10 C9 C11 114.1(9) . . ?
N2 C10 C9 177.8(11) . . ?
C16 C11 C12 117.9(9) . . ?
C16 C11 C9 120.9(9) . . ?
C12 C11 C9 121.2(10) . . ?
C11 C12 C13 119.5(11) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C14 C13 C12 122.6(11) . . ?
C14 C13 H13 118.7 . . ?
C12 C13 H13 118.7 . . ?
C13 C14 C15 116.8(9) . . ?
C13 C14 C17 121.7(9) . . ?
C15 C14 C17 121.5(11) . . ?
C16 C15 C14 121.7(10) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C15 C16 C11 121.4(10) . . ?
C15 C16 H16 119.3 . . ?
C11 C16 H16 119.3 . . ?
C21 C17 C18 114.7(9) . . ?
C21 C17 C14 122.0(10) . . ?
C18 C17 C14 123.3(10) . . ?
C19 C18 C17 119.6(11) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
N1 C19 C18 124.8(11) . . ?
N1 C19 H19 117.6 . . ?
C18 C19 H19 117.6 . . ?
N1 C20 C21 123.1(11) . . ?
N1 C20 H20 118.5 . . ?
C21 C20 H20 118.5 . . ?
C20 C21 C17 122.0(10) . . ?
C20 C21 H21 119.0 . . ?
C17 C21 H21 119.0 . . ?
H2A O2 H2B 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
O1 C1 C2 C7 -173.1(12) . . . . ?
O1 C1 C2 C3 6.6(17) . . . . ?
C7 C2 C3 C4 1.0(17) . . . . ?
C1 C2 C3 C4 -178.8(10) . . . . ?
C2 C3 C4 C5 -1.5(16) . . . . ?
C3 C4 C5 C6 2.0(16) . . . . ?
C3 C4 C5 C8 -179.3(10) . . . . ?
C4 C5 C6 C7 -2.1(16) . . . . ?
C8 C5 C6 C7 179.1(9) . . . . ?
C3 C2 C7 C6 -1.0(17) . . . . ?
C1 C2 C7 C6 178.8(9) . . . . ?
C5 C6 C7 C2 1.6(16) . . . . ?
C6 C5 C8 C9 178.0(11) . . . . ?
C4 C5 C8 C9 -0.8(19) . . . . ?
C5 C8 C9 C10 2.2(18) . . . . ?
C5 C8 C9 C11 179.3(10) . . . . ?
C8 C9 C11 C16 12.1(16) . . . . ?
C10 C9 C11 C16 -170.6(11) . . . . ?
C8 C9 C11 C12 -169.3(11) . . . . ?
C10 C9 C11 C12 8.0(14) . . . . ?
C16 C11 C12 C13 -1.7(15) . . . . ?
C9 C11 C12 C13 179.7(10) . . . . ?
C11 C12 C13 C14 1.7(17) . . . . ?
C12 C13 C14 C15 -0.7(18) . . . . ?
C12 C13 C14 C17 -179.1(11) . . . . ?
C13 C14 C15 C16 -0.2(17) . . . . ?
C17 C14 C15 C16 178.1(10) . . . . ?
C14 C15 C16 C11 0.2(16) . . . . ?
C12 C11 C16 C15 0.8(16) . . . . ?
C9 C11 C16 C15 179.4(9) . . . . ?
C13 C14 C17 C21 -147.8(14) . . . . ?
C15 C14 C17 C21 33.9(18) . . . . ?
C13 C14 C17 C18 32.3(18) . . . . ?
C15 C14 C17 C18 -146.0(12) . . . . ?
C21 C17 C18 C19 -1.1(18) . . . . ?
C14 C17 C18 C19 178.8(13) . . . . ?
C20 N1 C19 C18 0(2) . . . . ?
C17 C18 C19 N1 1(2) . . . . ?
C19 N1 C20 C21 -2(2) . . . . ?
N1 C20 C21 C17 2(2) . . . . ?
C18 C17 C21 C20 -0.7(19) . . . . ?
C14 C17 C21 C20 179.5(12) . . . . ?

_refine_diff_density_max         0.177
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.049

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_d8v19335
_database_code_depnum_ccdc_archive 'CCDC 2157127'
loop_
_audit_author_name
_audit_author_address
'Yipu Wang'
;East China University of Science and Technology
China
;
_audit_update_record             
;
2022-03-08 deposited with the CCDC.	2022-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H16 N2 O'
_chemical_formula_weight         312.36

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      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                   7.6270(3)
_cell_length_b                   33.7252(11)
_cell_length_c                   6.7050(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.9900(10)
_cell_angle_gamma                90
_cell_volume                     1620.77(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3930
_cell_measurement_theta_min      5.811
_cell_measurement_theta_max      54.717

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6316
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            7884
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.842
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             3148
_reflns_number_gt                2511
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0538P)²+0.2773P] 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     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3148
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1224
_refine_ls_wR_factor_gt          0.1099
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.0837(2) 0.70568(3) 0.2733(2) 0.0784(4) Uani 1 1 d . . . . .
N1 N 0.2570(2) 0.53930(5) 0.8646(2) 0.0785(5) Uani 1 1 d . . . . .
N2 N 0.5937(3) 0.28601(4) 0.3162(3) 0.0849(5) Uani 1 1 d . . . . .
C1 C 0.0366(2) 0.60666(4) 0.4726(2) 0.0525(4) Uani 1 1 d . . . . .
H1 H 0.0378 0.5923 0.5915 0.063 Uiso 1 1 calc R U . . .
C2 C -0.0196(2) 0.64545(5) 0.4524(2) 0.0585(4) Uani 1 1 d . . . . .
H2 H -0.0558 0.6570 0.5581 0.070 Uiso 1 1 calc R U . . .
C3 C -0.0235(2) 0.66772(4) 0.2776(2) 0.0548(4) Uani 1 1 d . . . . .
C4 C 0.0297(2) 0.65038(5) 0.1207(2) 0.0613(4) Uani 1 1 d . . . . .
H4 H 0.0281 0.6649 0.0022 0.074 Uiso 1 1 calc R U . . .
C5 C 0.0853(2) 0.61120(5) 0.1420(2) 0.0573(4) Uani 1 1 d . . . . .
H5 H 0.1196 0.5996 0.0350 0.069 Uiso 1 1 calc R U . . .
C6 C 0.0920(2) 0.58834(4) 0.3174(2) 0.0455(4) Uani 1 1 d . . . . .
C7 C 0.1531(2) 0.54736(4) 0.3208(2) 0.0478(4) Uani 1 1 d . . . . .
H7 H 0.1498 0.5379 0.1893 0.057 Uiso 1 1 calc R U . . .
C8 C 0.21340(19) 0.52062(4) 0.4784(2) 0.0418(3) Uani 1 1 d . . . . .
C9 C 0.2345(2) 0.53145(4) 0.6926(2) 0.0510(4) Uani 1 1 d . . . . .
C10 C 0.27462(18) 0.47983(4) 0.4508(2) 0.0425(3) Uani 1 1 d . . . . .
C11 C 0.2513(2) 0.46451(4) 0.2504(2) 0.0524(4) Uani 1 1 d . . . . .
H11 H 0.1927 0.4798 0.1308 0.063 Uiso 1 1 calc R U . . .
C12 C 0.3134(2) 0.42712(4) 0.2260(2) 0.0528(4) Uani 1 1 d . . . . .
H12 H 0.2970 0.4179 0.0901 0.063 Uiso 1 1 calc R U . . .
C13 C 0.39974(19) 0.40281(4) 0.3989(2) 0.0460(3) Uani 1 1 d . . . . .
C14 C 0.4216(2) 0.41799(4) 0.5979(2) 0.0527(4) Uani 1 1 d . . . . .
H14 H 0.4787 0.4025 0.7172 0.063 Uiso 1 1 calc R U . . .
C15 C 0.3608(2) 0.45557(4) 0.6236(2) 0.0500(4) Uani 1 1 d . . . . .
H15 H 0.3781 0.4648 0.7597 0.060 Uiso 1 1 calc R U . . .
C16 C 0.4658(2) 0.36247(4) 0.3700(2) 0.0514(4) Uani 1 1 d . . . . .
C17 C 0.5161(3) 0.35263(5) 0.1965(3) 0.0715(5) Uani 1 1 d . . . . .
H17 H 0.5092 0.3715 0.0931 0.086 Uiso 1 1 calc R U . . .
C18 C 0.5766(3) 0.31469(6) 0.1772(4) 0.0870(6) Uani 1 1 d . . . . .
H18 H 0.6076 0.3090 0.0577 0.104 Uiso 1 1 calc R U . . .
C19 C 0.5472(3) 0.29556(5) 0.4828(3) 0.0794(6) Uani 1 1 d . . . . .
H19 H 0.5586 0.2761 0.5850 0.095 Uiso 1 1 calc R U . . .
C20 C 0.4828(3) 0.33242(5) 0.5155(3) 0.0652(5) Uani 1 1 d . . . . .
H20 H 0.4508 0.3370 0.6355 0.078 Uiso 1 1 calc R U . . .
C21 C -0.0814(3) 0.73042(6) 0.1015(3) 0.0923(7) Uani 1 1 d . . . . .
H21A H -0.1564 0.7186 -0.0304 0.138 Uiso 1 1 calc R U . . .
H21B H 0.0445 0.7332 0.1037 0.138 Uiso 1 1 calc R U . . .
H21C H -0.1308 0.7560 0.1156 0.138 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
O1 C3 1.3569(18) . ?
O1 C21 1.427(2) . ?
N1 C9 1.1377(18) . ?
N2 C18 1.318(3) . ?
N2 C19 1.323(3) . ?
C1 C2 1.369(2) . ?
C1 C6 1.3941(19) . ?
C1 H1 0.9300 . ?
C2 C3 1.384(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(2) . ?
C4 C5 1.380(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.4559(19) . ?
C7 C8 1.3450(19) . ?
C7 H7 0.9300 . ?
C8 C9 1.4365(18) . ?
C8 C10 1.4844(18) . ?
C10 C15 1.3868(18) . ?
C10 C11 1.3936(19) . ?
C11 C12 1.376(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.3882(19) . ?
C12 H12 0.9300 . ?
C13 C14 1.3853(19) . ?
C13 C16 1.4864(19) . ?
C14 C15 1.381(2) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C20 1.382(2) . ?
C16 C17 1.384(2) . ?
C17 C18 1.381(2) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.381(2) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C21 118.15(13) . . ?
C18 N2 C19 115.37(16) . . ?
C2 C1 C6 120.97(14) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C1 C2 C3 121.17(14) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
O1 C3 C4 124.66(14) . . ?
O1 C3 C2 116.06(14) . . ?
C4 C3 C2 119.27(14) . . ?
C5 C4 C3 119.12(14) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 122.62(14) . . ?
C4 C5 H5 118.7 . . ?
C6 C5 H5 118.7 . . ?
C5 C6 C1 116.86(13) . . ?
C5 C6 C7 117.26(12) . . ?
C1 C6 C7 125.88(13) . . ?
C8 C7 C6 132.09(12) . . ?
C8 C7 H7 114.0 . . ?
C6 C7 H7 114.0 . . ?
C7 C8 C9 120.41(12) . . ?
C7 C8 C10 124.14(12) . . ?
C9 C8 C10 115.31(11) . . ?
N1 C9 C8 177.59(17) . . ?
C15 C10 C11 117.05(13) . . ?
C15 C10 C8 121.48(12) . . ?
C11 C10 C8 121.46(12) . . ?
C12 C11 C10 121.25(13) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 121.75(13) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C14 C13 C12 116.92(13) . . ?
C14 C13 C16 121.95(13) . . ?
C12 C13 C16 121.13(13) . . ?
C15 C14 C13 121.64(13) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C14 C15 C10 121.38(13) . . ?
C14 C15 H15 119.3 . . ?
C10 C15 H15 119.3 . . ?
C20 C16 C17 115.57(15) . . ?
C20 C16 C13 122.24(14) . . ?
C17 C16 C13 122.19(14) . . ?
C18 C17 C16 119.88(18) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
N2 C18 C17 124.7(2) . . ?
N2 C18 H18 117.7 . . ?
C17 C18 H18 117.7 . . ?
N2 C19 C20 124.44(18) . . ?
N2 C19 H19 117.8 . . ?
C20 C19 H19 117.8 . . ?
C19 C20 C16 120.05(17) . . ?
C19 C20 H20 120.0 . . ?
C16 C20 H20 120.0 . . ?
O1 C21 H21A 109.5 . . ?
O1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
C6 C1 C2 C3 0.1(3) . . . . ?
C21 O1 C3 C4 -4.1(3) . . . . ?
C21 O1 C3 C2 176.94(17) . . . . ?
C1 C2 C3 O1 179.26(15) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
O1 C3 C4 C5 -178.87(16) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C4 C5 C6 C1 1.0(2) . . . . ?
C4 C5 C6 C7 179.98(15) . . . . ?
C2 C1 C6 C5 -0.7(2) . . . . ?
C2 C1 C6 C7 -179.56(15) . . . . ?
C5 C6 C7 C8 163.27(16) . . . . ?
C1 C6 C7 C8 -17.9(3) . . . . ?
C6 C7 C8 C9 -2.9(2) . . . . ?
C6 C7 C8 C10 -178.50(14) . . . . ?
C7 C8 C10 C15 170.40(13) . . . . ?
C9 C8 C10 C15 -5.38(19) . . . . ?
C7 C8 C10 C11 -8.3(2) . . . . ?
C9 C8 C10 C11 175.90(13) . . . . ?
C15 C10 C11 C12 -0.8(2) . . . . ?
C8 C10 C11 C12 178.01(14) . . . . ?
C10 C11 C12 C13 0.8(2) . . . . ?
C11 C12 C13 C14 -0.3(2) . . . . ?
C11 C12 C13 C16 179.91(14) . . . . ?
C12 C13 C14 C15 -0.1(2) . . . . ?
C16 C13 C14 C15 179.64(14) . . . . ?
C13 C14 C15 C10 0.1(2) . . . . ?
C11 C10 C15 C14 0.3(2) . . . . ?
C8 C10 C15 C14 -178.45(13) . . . . ?
C14 C13 C16 C20 26.4(2) . . . . ?
C12 C13 C16 C20 -153.85(15) . . . . ?
C14 C13 C16 C17 -152.99(16) . . . . ?
C12 C13 C16 C17 26.8(2) . . . . ?
C20 C16 C17 C18 0.6(3) . . . . ?
C13 C16 C17 C18 180.00(17) . . . . ?
C19 N2 C18 C17 0.3(3) . . . . ?
C16 C17 C18 N2 -0.9(3) . . . . ?
C18 N2 C19 C20 0.6(3) . . . . ?
N2 C19 C20 C16 -0.9(3) . . . . ?
C17 C16 C20 C19 0.3(2) . . . . ?
C13 C16 C20 C19 -179.15(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C19 H19 N2 0.93 2.57 3.485(2) 169.9 4_566
C19 H19 N2 0.93 2.57 3.485(2) 169.9 4_566

_refine_diff_density_max         0.138
_refine_diff_density_min         -0.118
_refine_diff_density_rms         0.025

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_d8v19550
_database_code_depnum_ccdc_archive 'CCDC 2157128'
loop_
_audit_author_name
_audit_author_address
'Yipu Wang'
;East China University of Science and Technology
China
;
_audit_update_record             
;
2022-03-08 deposited with the CCDC.	2022-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H19 N3'
_chemical_formula_weight         325.40

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                   25.826(3)
_cell_length_b                   5.9172(6)
_cell_length_c                   25.826(3)
_cell_angle_alpha                90
_cell_angle_beta                 114.54
_cell_angle_gamma                90
_cell_volume                     3590.3(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1698
_cell_measurement_theta_min      4.337
_cell_measurement_theta_max      54.125

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_F_000             1376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6557
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            16045
_diffrn_reflns_av_unetI/netI     0.1228
_diffrn_reflns_av_R_equivalents  0.0763
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.237
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             6619
_reflns_number_gt                2308
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0524P)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     SHELXL
_refine_ls_extinction_coef       0.0020(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6619
_refine_ls_number_parameters     456
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2159
_refine_ls_R_factor_gt           0.0670
_refine_ls_wR_factor_ref         0.1823
_refine_ls_wR_factor_gt          0.1212
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_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 0.88540(18) -0.1434(6) 0.37018(15) 0.0831(11) Uani 1 1 d . . . . .
N2 N 0.78584(19) 0.9445(8) 0.6099(2) 0.1296(17) Uani 1 1 d . . . . .
N3 N 1.16725(18) 0.7224(7) 0.75069(16) 0.0938(12) Uani 1 1 d . . . . .
C1 C 0.83447(17) 0.0761(8) 0.4112(2) 0.0846(14) Uani 1 1 d . . . . .
H1 H 0.7995 0.1100 0.4115 0.102 Uiso 1 1 calc R U . . .
C2 C 0.83766(19) -0.0816(8) 0.3736(2) 0.0897(15) Uani 1 1 d . . . . .
H2 H 0.8040 -0.1495 0.3488 0.108 Uiso 1 1 calc R U . . .
C3 C 0.93134(18) -0.0340(8) 0.4051(2) 0.0788(13) Uani 1 1 d . . . . .
H3 H 0.9657 -0.0683 0.4033 0.095 Uiso 1 1 calc R U . . .
C4 C 0.93211(17) 0.1271(7) 0.44390(18) 0.0717(12) Uani 1 1 d . . . . .
H4 H 0.9661 0.1972 0.4671 0.086 Uiso 1 1 calc R U . . .
C5 C 0.88254(17) 0.1835(7) 0.44812(17) 0.0623(11) Uani 1 1 d . . . . .
C6 C 0.88212(16) 0.3468(7) 0.49080(17) 0.0613(11) Uani 1 1 d . . . . .
C7 C 0.91328(16) 0.5442(7) 0.50192(18) 0.0693(12) Uani 1 1 d . . . . .
H7 H 0.9345 0.5765 0.4813 0.083 Uiso 1 1 calc R U . . .
C8 C 0.91376(17) 0.6945(7) 0.54272(18) 0.0721(12) Uani 1 1 d . . . . .
H8 H 0.9349 0.8269 0.5488 0.086 Uiso 1 1 calc R U . . .
C9 C 0.88332(17) 0.6518(7) 0.57486(18) 0.0664(11) Uani 1 1 d . . . . .
C10 C 0.85061(17) 0.4584(8) 0.56305(19) 0.0789(13) Uani 1 1 d . . . . .
H10 H 0.8285 0.4290 0.5830 0.095 Uiso 1 1 calc R U . . .
C11 C 0.85027(16) 0.3081(7) 0.52204(19) 0.0756(13) Uani 1 1 d . . . . .
H11 H 0.8282 0.1779 0.5152 0.091 Uiso 1 1 calc R U . . .
C12 C 0.8844(2) 0.8138(7) 0.6191(2) 0.0757(13) Uani 1 1 d . . . . .
C13 C 0.8305(2) 0.8892(8) 0.6149(2) 0.0923(16) Uani 1 1 d . . . . .
C14 C 0.9305(2) 0.9008(7) 0.66091(19) 0.0759(13) Uani 1 1 d . . . . .
H14 H 0.9225 1.0168 0.6808 0.091 Uiso 1 1 calc R U . . .
C15 C 0.99070(19) 0.8494(7) 0.68132(17) 0.0668(11) Uani 1 1 d . . . . .
C16 C 1.0305(2) 0.9973(7) 0.71854(19) 0.0784(13) Uani 1 1 d . . . . .
H16 H 1.0174 1.1306 0.7280 0.094 Uiso 1 1 calc R U . . .
C17 C 1.0880(2) 0.9575(8) 0.74214(18) 0.0812(14) Uani 1 1 d . . . . .
H17 H 1.1125 1.0622 0.7673 0.097 Uiso 1 1 calc R U . . .
C18 C 1.1102(2) 0.7618(8) 0.72884(18) 0.0732(12) Uani 1 1 d . . . . .
C19 C 1.07070(19) 0.6078(7) 0.69249(17) 0.0710(12) Uani 1 1 d . . . . .
H19 H 1.0836 0.4730 0.6835 0.085 Uiso 1 1 calc R U . . .
C20 C 1.01376(19) 0.6507(7) 0.66990(16) 0.0678(11) Uani 1 1 d . . . . .
H20 H 0.9891 0.5436 0.6459 0.081 Uiso 1 1 calc R U . . .
C21 C 1.20760(19) 0.8766(8) 0.7907(2) 0.1188(18) Uani 1 1 d . . . . .
H21A H 1.2147 0.9998 0.7704 0.178 Uiso 1 1 calc R U . . .
H21B H 1.2426 0.7983 0.8122 0.178 Uiso 1 1 calc R U . . .
H21C H 1.1923 0.9341 0.8162 0.178 Uiso 1 1 calc R U . . .
C22 C 1.19066(19) 0.5345(9) 0.7329(2) 0.124(2) Uani 1 1 d . . . . .
H22A H 1.1685 0.4017 0.7308 0.186 Uiso 1 1 calc R U . . .
H22B H 1.2292 0.5103 0.7598 0.186 Uiso 1 1 calc R U . . .
H22C H 1.1899 0.5654 0.6961 0.186 Uiso 1 1 calc R U . . .
N4 N 0.6255(2) -0.6684(7) 0.4833(2) 0.1037(14) Uani 1 1 d . . . . .
N5 N 0.69810(17) 0.4428(8) 0.7961(2) 0.1262(17) Uani 1 1 d . . . . .
N6 N 0.31929(15) 0.2689(7) 0.59123(17) 0.0891(12) Uani 1 1 d . . . . .
C23 C 0.66890(19) -0.4540(9) 0.5692(2) 0.0997(16) Uani 1 1 d . . . . .
H23 H 0.7015 -0.4258 0.6021 0.120 Uiso 1 1 calc R U . . .
C24 C 0.6695(2) -0.6174(11) 0.5317(3) 0.1120(19) Uani 1 1 d . . . . .
H24 H 0.7031 -0.6979 0.5408 0.134 Uiso 1 1 calc R U . . .
C25 C 0.5786(2) -0.5485(9) 0.4722(2) 0.0946(15) Uani 1 1 d . . . . .
H25 H 0.5469 -0.5774 0.4385 0.113 Uiso 1 1 calc R U . . .
C26 C 0.57435(19) -0.3836(8) 0.5079(2) 0.0856(14) Uani 1 1 d . . . . .
H26 H 0.5402 -0.3062 0.4980 0.103 Uiso 1 1 calc R U . . .
C27 C 0.62013(18) -0.3318(8) 0.5582(2) 0.0710(12) Uani 1 1 d . . . . .
C28 C 0.61583(17) -0.1630(8) 0.5985(2) 0.0701(12) Uani 1 1 d . . . . .
C29 C 0.58307(17) 0.0306(8) 0.58021(19) 0.0761(13) Uani 1 1 d . . . . .
H29 H 0.5637 0.0574 0.5414 0.091 Uiso 1 1 calc R U . . .
C30 C 0.57860(17) 0.1838(8) 0.6181(2) 0.0799(13) Uani 1 1 d . . . . .
H30 H 0.5564 0.3124 0.6043 0.096 Uiso 1 1 calc R U . . .
C31 C 0.60656(16) 0.1511(8) 0.6766(2) 0.0691(12) Uani 1 1 d . . . . .
C32 C 0.63981(17) -0.0403(8) 0.6946(2) 0.0811(14) Uani 1 1 d . . . . .
H32 H 0.6597 -0.0657 0.7334 0.097 Uiso 1 1 calc R U . . .
C33 C 0.64446(17) -0.1942(8) 0.6571(2) 0.0852(14) Uani 1 1 d . . . . .
H33 H 0.6671 -0.3216 0.6711 0.102 Uiso 1 1 calc R U . . .
C34 C 0.60202(18) 0.3177(8) 0.71720(18) 0.0707(12) Uani 1 1 d . . . . .
C35 C 0.6553(2) 0.3897(9) 0.7612(2) 0.0922(15) Uani 1 1 d . . . . .
C36 C 0.55492(18) 0.4128(7) 0.71719(17) 0.0745(12) Uani 1 1 d . . . . .
H36 H 0.5618 0.5302 0.7432 0.089 Uiso 1 1 calc R U . . .
C37 C 0.49530(17) 0.3654(7) 0.68397(17) 0.0656(11) Uani 1 1 d . . . . .
C38 C 0.47354(17) 0.1674(7) 0.65293(17) 0.0706(12) Uani 1 1 d . . . . .
H38 H 0.4987 0.0559 0.6524 0.085 Uiso 1 1 calc R U . . .
C39 C 0.41600(17) 0.1331(7) 0.62317(17) 0.0733(12) Uani 1 1 d . . . . .
H39 H 0.4032 -0.0006 0.6030 0.088 Uiso 1 1 calc R U . . .
C40 C 0.37593(18) 0.2966(8) 0.62265(18) 0.0714(12) Uani 1 1 d . . . . .
C41 C 0.39779(19) 0.4880(8) 0.65640(19) 0.0820(14) Uani 1 1 d . . . . .
H41 H 0.3729 0.5956 0.6594 0.098 Uiso 1 1 calc R U . . .
C42 C 0.45523(19) 0.5198(8) 0.68513(17) 0.0787(13) Uani 1 1 d . . . . .
H42 H 0.4681 0.6510 0.7065 0.094 Uiso 1 1 calc R U . . .
C43 C 0.29809(19) 0.0920(9) 0.5491(2) 0.125(2) Uani 1 1 d . . . . .
H43A H 0.3215 0.0823 0.5284 0.187 Uiso 1 1 calc R U . . .
H43B H 0.2596 0.1256 0.5232 0.187 Uiso 1 1 calc R U . . .
H43C H 0.2991 -0.0496 0.5676 0.187 Uiso 1 1 calc R U . . .
C44 C 0.27873(18) 0.4298(8) 0.5951(2) 0.123(2) Uani 1 1 d . . . . .
H44A H 0.2870 0.4570 0.6344 0.185 Uiso 1 1 calc R U . . .
H44B H 0.2409 0.3699 0.5762 0.185 Uiso 1 1 calc R U . . .
H44C H 0.2814 0.5692 0.5774 0.185 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 C3 1.323(5) . ?
N1 C2 1.323(5) . ?
N2 C13 1.153(5) . ?
N3 C18 1.360(5) . ?
N3 C22 1.430(5) . ?
N3 C21 1.447(5) . ?
C1 C5 1.368(5) . ?
C1 C2 1.374(5) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 C4 1.378(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.469(5) . ?
C6 C7 1.379(5) . ?
C6 C11 1.390(5) . ?
C7 C8 1.375(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.383(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.379(5) . ?
C9 C12 1.484(5) . ?
C10 C11 1.380(5) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C14 1.334(5) . ?
C12 C13 1.423(6) . ?
C14 C15 1.452(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.387(5) . ?
C15 C20 1.404(5) . ?
C16 C17 1.372(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.398(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.399(5) . ?
C19 C20 1.362(5) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
N4 C24 1.328(6) . ?
N4 C25 1.328(5) . ?
N5 C35 1.143(5) . ?
N6 C40 1.356(5) . ?
N6 C43 1.444(5) . ?
N6 C44 1.450(5) . ?
C23 C24 1.374(6) . ?
C23 C27 1.376(5) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.378(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.380(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.479(6) . ?
C28 C29 1.385(5) . ?
C28 C33 1.394(5) . ?
C29 C30 1.373(5) . ?
C29 H29 0.9300 . ?
C30 C31 1.392(5) . ?
C30 H30 0.9300 . ?
C31 C32 1.380(5) . ?
C31 C34 1.479(5) . ?
C32 C33 1.369(5) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
C34 C36 1.340(5) . ?
C34 C35 1.438(6) . ?
C36 C37 1.445(5) . ?
C36 H36 0.9300 . ?
C37 C42 1.390(5) . ?
C37 C38 1.399(5) . ?
C38 C39 1.375(5) . ?
C38 H38 0.9300 . ?
C39 C40 1.413(5) . ?
C39 H39 0.9300 . ?
C40 C41 1.397(5) . ?
C41 C42 1.368(5) . ?
C41 H41 0.9300 . ?
C42 H42 0.9300 . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C2 114.6(4) . . ?
C18 N3 C22 122.0(4) . . ?
C18 N3 C21 121.5(4) . . ?
C22 N3 C21 116.4(4) . . ?
C5 C1 C2 120.3(4) . . ?
C5 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
N1 C2 C1 124.5(4) . . ?
N1 C2 H2 117.8 . . ?
C1 C2 H2 117.8 . . ?
N1 C3 C4 124.9(4) . . ?
N1 C3 H3 117.5 . . ?
C4 C3 H3 117.5 . . ?
C5 C4 C3 119.7(4) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C1 C5 C4 116.0(4) . . ?
C1 C5 C6 122.8(4) . . ?
C4 C5 C6 121.2(4) . . ?
C7 C6 C11 117.0(4) . . ?
C7 C6 C5 121.8(4) . . ?
C11 C6 C5 121.2(4) . . ?
C8 C7 C6 121.7(4) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C7 C8 C9 121.0(4) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C10 C9 C8 117.9(4) . . ?
C10 C9 C12 121.4(4) . . ?
C8 C9 C12 120.7(4) . . ?
C9 C10 C11 120.8(4) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C6 121.5(4) . . ?
C10 C11 H11 119.2 . . ?
C6 C11 H11 119.2 . . ?
C14 C12 C13 117.2(5) . . ?
C14 C12 C9 126.7(4) . . ?
C13 C12 C9 116.0(4) . . ?
N2 C13 C12 177.5(6) . . ?
C12 C14 C15 132.4(4) . . ?
C12 C14 H14 113.8 . . ?
C15 C14 H14 113.8 . . ?
C16 C15 C20 114.7(4) . . ?
C16 C15 C14 119.5(4) . . ?
C20 C15 C14 125.7(4) . . ?
C17 C16 C15 123.6(4) . . ?
C17 C16 H16 118.2 . . ?
C15 C16 H16 118.2 . . ?
C16 C17 C18 120.9(4) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
N3 C18 C17 121.7(4) . . ?
N3 C18 C19 122.0(5) . . ?
C17 C18 C19 116.4(4) . . ?
C20 C19 C18 121.6(4) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C19 C20 C15 122.9(4) . . ?
C19 C20 H20 118.6 . . ?
C15 C20 H20 118.6 . . ?
N3 C21 H21A 109.5 . . ?
N3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N3 C22 H22A 109.5 . . ?
N3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 N4 C25 115.5(5) . . ?
C40 N6 C43 121.0(4) . . ?
C40 N6 C44 120.6(4) . . ?
C43 N6 C44 118.0(4) . . ?
C24 C23 C27 120.2(5) . . ?
C24 C23 H23 119.9 . . ?
C27 C23 H23 119.9 . . ?
N4 C24 C23 124.5(5) . . ?
N4 C24 H24 117.7 . . ?
C23 C24 H24 117.7 . . ?
N4 C25 C26 123.5(5) . . ?
N4 C25 H25 118.2 . . ?
C26 C25 H25 118.2 . . ?
C25 C26 C27 120.8(5) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 H26 119.6 . . ?
C23 C27 C26 115.5(5) . . ?
C23 C27 C28 122.7(5) . . ?
C26 C27 C28 121.8(4) . . ?
C29 C28 C33 117.0(5) . . ?
C29 C28 C27 122.2(5) . . ?
C33 C28 C27 120.9(5) . . ?
C30 C29 C28 121.6(4) . . ?
C30 C29 H29 119.2 . . ?
C28 C29 H29 119.2 . . ?
C29 C30 C31 121.5(5) . . ?
C29 C30 H30 119.3 . . ?
C31 C30 H30 119.3 . . ?
C32 C31 C30 116.7(5) . . ?
C32 C31 C34 122.0(4) . . ?
C30 C31 C34 121.3(5) . . ?
C33 C32 C31 122.2(5) . . ?
C33 C32 H32 118.9 . . ?
C31 C32 H32 118.9 . . ?
C32 C33 C28 121.1(5) . . ?
C32 C33 H33 119.5 . . ?
C28 C33 H33 119.5 . . ?
C36 C34 C35 116.5(5) . . ?
C36 C34 C31 128.3(4) . . ?
C35 C34 C31 115.3(4) . . ?
N5 C35 C34 178.6(6) . . ?
C34 C36 C37 131.4(4) . . ?
C34 C36 H36 114.3 . . ?
C37 C36 H36 114.3 . . ?
C42 C37 C38 115.9(4) . . ?
C42 C37 C36 118.6(4) . . ?
C38 C37 C36 125.3(4) . . ?
C39 C38 C37 121.8(4) . . ?
C39 C38 H38 119.1 . . ?
C37 C38 H38 119.1 . . ?
C38 C39 C40 121.4(4) . . ?
C38 C39 H39 119.3 . . ?
C40 C39 H39 119.3 . . ?
N6 C40 C41 121.8(4) . . ?
N6 C40 C39 121.8(4) . . ?
C41 C40 C39 116.4(4) . . ?
C42 C41 C40 121.0(4) . . ?
C42 C41 H41 119.5 . . ?
C40 C41 H41 119.5 . . ?
C41 C42 C37 123.2(4) . . ?
C41 C42 H42 118.4 . . ?
C37 C42 H42 118.4 . . ?
N6 C43 H43A 109.5 . . ?
N6 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
N6 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
N6 C44 H44A 109.5 . . ?
N6 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
N6 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 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
C3 N1 C2 C1 -2.5(7) . . . . ?
C5 C1 C2 N1 0.8(8) . . . . ?
C2 N1 C3 C4 2.1(7) . . . . ?
N1 C3 C4 C5 0.0(7) . . . . ?
C2 C1 C5 C4 1.4(6) . . . . ?
C2 C1 C5 C6 -177.5(4) . . . . ?
C3 C4 C5 C1 -1.7(6) . . . . ?
C3 C4 C5 C6 177.2(4) . . . . ?
C1 C5 C6 C7 -138.5(4) . . . . ?
C4 C5 C6 C7 42.7(6) . . . . ?
C1 C5 C6 C11 41.8(6) . . . . ?
C4 C5 C6 C11 -137.0(4) . . . . ?
C11 C6 C7 C8 1.1(6) . . . . ?
C5 C6 C7 C8 -178.6(4) . . . . ?
C6 C7 C8 C9 0.8(6) . . . . ?
C7 C8 C9 C10 -2.7(6) . . . . ?
C7 C8 C9 C12 179.5(4) . . . . ?
C8 C9 C10 C11 2.7(6) . . . . ?
C12 C9 C10 C11 -179.5(4) . . . . ?
C9 C10 C11 C6 -0.8(7) . . . . ?
C7 C6 C11 C10 -1.1(6) . . . . ?
C5 C6 C11 C10 178.6(4) . . . . ?
C10 C9 C12 C14 130.8(5) . . . . ?
C8 C9 C12 C14 -51.5(6) . . . . ?
C10 C9 C12 C13 -51.7(6) . . . . ?
C8 C9 C12 C13 126.1(4) . . . . ?
C13 C12 C14 C15 173.1(4) . . . . ?
C9 C12 C14 C15 -9.4(8) . . . . ?
C12 C14 C15 C16 167.3(4) . . . . ?
C12 C14 C15 C20 -17.4(7) . . . . ?
C20 C15 C16 C17 1.0(6) . . . . ?
C14 C15 C16 C17 176.8(4) . . . . ?
C15 C16 C17 C18 1.0(7) . . . . ?
C22 N3 C18 C17 -173.5(4) . . . . ?
C21 N3 C18 C17 2.6(6) . . . . ?
C22 N3 C18 C19 7.3(7) . . . . ?
C21 N3 C18 C19 -176.5(4) . . . . ?
C16 C17 C18 N3 178.3(4) . . . . ?
C16 C17 C18 C19 -2.5(6) . . . . ?
N3 C18 C19 C20 -178.7(4) . . . . ?
C17 C18 C19 C20 2.1(6) . . . . ?
C18 C19 C20 C15 -0.2(6) . . . . ?
C16 C15 C20 C19 -1.4(6) . . . . ?
C14 C15 C20 C19 -176.9(4) . . . . ?
C25 N4 C24 C23 0.1(8) . . . . ?
C27 C23 C24 N4 0.9(9) . . . . ?
C24 N4 C25 C26 -0.9(7) . . . . ?
N4 C25 C26 C27 0.6(8) . . . . ?
C24 C23 C27 C26 -1.1(7) . . . . ?
C24 C23 C27 C28 176.4(5) . . . . ?
C25 C26 C27 C23 0.4(7) . . . . ?
C25 C26 C27 C28 -177.1(4) . . . . ?
C23 C27 C28 C29 146.5(4) . . . . ?
C26 C27 C28 C29 -36.1(6) . . . . ?
C23 C27 C28 C33 -34.2(6) . . . . ?
C26 C27 C28 C33 143.1(4) . . . . ?
C33 C28 C29 C30 -0.5(6) . . . . ?
C27 C28 C29 C30 178.7(4) . . . . ?
C28 C29 C30 C31 -0.3(6) . . . . ?
C29 C30 C31 C32 1.2(6) . . . . ?
C29 C30 C31 C34 179.5(4) . . . . ?
C30 C31 C32 C33 -1.3(6) . . . . ?
C34 C31 C32 C33 -179.5(4) . . . . ?
C31 C32 C33 C28 0.5(7) . . . . ?
C29 C28 C33 C32 0.5(6) . . . . ?
C27 C28 C33 C32 -178.8(4) . . . . ?
C32 C31 C34 C36 -133.0(5) . . . . ?
C30 C31 C34 C36 48.8(6) . . . . ?
C32 C31 C34 C35 48.8(6) . . . . ?
C30 C31 C34 C35 -129.4(4) . . . . ?
C35 C34 C36 C37 -172.6(4) . . . . ?
C31 C34 C36 C37 9.2(8) . . . . ?
C34 C36 C37 C42 -167.6(4) . . . . ?
C34 C36 C37 C38 16.7(7) . . . . ?
C42 C37 C38 C39 3.0(6) . . . . ?
C36 C37 C38 C39 178.7(4) . . . . ?
C37 C38 C39 C40 -0.2(6) . . . . ?
C43 N6 C40 C41 168.9(4) . . . . ?
C44 N6 C40 C41 -5.0(6) . . . . ?
C43 N6 C40 C39 -11.4(6) . . . . ?
C44 N6 C40 C39 174.8(4) . . . . ?
C38 C39 C40 N6 176.8(4) . . . . ?
C38 C39 C40 C41 -3.4(6) . . . . ?
N6 C40 C41 C42 -176.0(4) . . . . ?
C39 C40 C41 C42 4.2(6) . . . . ?
C40 C41 C42 C37 -1.4(7) . . . . ?
C38 C37 C42 C41 -2.3(6) . . . . ?
C36 C37 C42 C41 -178.3(4) . . . . ?

_refine_diff_density_max         0.130
_refine_diff_density_min         -0.117
_refine_diff_density_rms         0.031

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_d8v19334_0m
_database_code_depnum_ccdc_archive 'CCDC 2157129'
loop_
_audit_author_name
_audit_author_address
'Yipu Wang'
;East China University of Science and Technology
China
;
_audit_update_record             
;
2022-03-08 deposited with the CCDC.	2022-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H14 N2'
_chemical_formula_weight         282.33

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/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   6.7926(5)
_cell_length_b                   7.0902(5)
_cell_length_c                   31.308(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.003(2)
_cell_angle_gamma                90
_cell_volume                     1502.07(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4238
_cell_measurement_theta_min      5.224
_cell_measurement_theta_max      54.560

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4709
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            13996
_diffrn_reflns_av_unetI/netI     0.0630
_diffrn_reflns_av_R_equivalents  0.0759
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.612
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_full        25.242
_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             2781
_reflns_number_gt                2069
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0686P)²+0.2551P] 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     SHELXL
_refine_ls_extinction_coef       0.048(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2781
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1530
_refine_ls_wR_factor_gt          0.1353
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.7573(2) 0.2194(3) 0.43398(5) 0.0636(5) Uani 1 1 d . . . . .
N2 N 0.1898(3) 0.3492(3) 0.71540(5) 0.0672(5) Uani 1 1 d . . . . .
C1 C 0.4133(3) 0.2701(3) 0.34954(6) 0.0486(5) Uani 1 1 d . . . . .
H1 H 0.5119 0.3395 0.3648 0.058 Uiso 1 1 calc R U . . .
C2 C 0.4181(3) 0.2483(3) 0.30593(6) 0.0576(5) Uani 1 1 d . . . . .
H2 H 0.5196 0.3029 0.2921 0.069 Uiso 1 1 calc R U . . .
C3 C 0.2744(3) 0.1469(3) 0.28286(6) 0.0623(6) Uani 1 1 d . . . . .
H3 H 0.2797 0.1303 0.2535 0.075 Uiso 1 1 calc R U . . .
C4 C 0.1230(3) 0.0699(3) 0.30306(6) 0.0667(6) Uani 1 1 d . . . . .
H4 H 0.0242 0.0023 0.2873 0.080 Uiso 1 1 calc R U . . .
C5 C 0.1159(3) 0.0919(3) 0.34677(6) 0.0549(5) Uani 1 1 d . . . . .
H5 H 0.0112 0.0405 0.3601 0.066 Uiso 1 1 calc R U . . .
C6 C 0.2635(2) 0.1901(2) 0.37102(5) 0.0400(4) Uani 1 1 d . . . . .
C7 C 0.2478(2) 0.2071(2) 0.41711(5) 0.0417(4) Uani 1 1 d . . . . .
H7 H 0.1199 0.2016 0.4255 0.050 Uiso 1 1 calc R U . . .
C8 C 0.3910(2) 0.2296(2) 0.44927(5) 0.0386(4) Uani 1 1 d . . . . .
C9 C 0.5952(3) 0.2256(3) 0.44015(5) 0.0444(4) Uani 1 1 d . . . . .
C10 C 0.3561(2) 0.2496(2) 0.49515(5) 0.0393(4) Uani 1 1 d . . . . .
C11 C 0.1684(3) 0.2696(3) 0.50833(6) 0.0584(6) Uani 1 1 d . . . . .
H11 H 0.0604 0.2713 0.4879 0.070 Uiso 1 1 calc R U . . .
C12 C 0.1375(3) 0.2872(3) 0.55093(6) 0.0590(6) Uani 1 1 d . . . . .
H12 H 0.0091 0.3004 0.5587 0.071 Uiso 1 1 calc R U . . .
C13 C 0.2935(3) 0.2858(2) 0.58276(5) 0.0417(4) Uani 1 1 d . . . . .
C14 C 0.4817(3) 0.2660(3) 0.56974(5) 0.0466(5) Uani 1 1 d . . . . .
H14 H 0.5893 0.2639 0.5902 0.056 Uiso 1 1 calc R U . . .
C15 C 0.5132(2) 0.2492(3) 0.52695(5) 0.0455(5) Uani 1 1 d . . . . .
H15 H 0.6416 0.2373 0.5192 0.055 Uiso 1 1 calc R U . . .
C16 C 0.2581(3) 0.3070(2) 0.62851(5) 0.0428(4) Uani 1 1 d . . . . .
C17 C 0.1111(3) 0.4228(3) 0.64141(6) 0.0586(6) Uani 1 1 d . . . . .
H17 H 0.0306 0.4895 0.6211 0.070 Uiso 1 1 calc R U . . .
C18 C 0.0838(3) 0.4397(3) 0.68426(6) 0.0687(6) Uani 1 1 d . . . . .
H18 H -0.0156 0.5199 0.6919 0.082 Uiso 1 1 calc R U . . .
C19 C 0.3301(3) 0.2386(3) 0.70276(6) 0.0633(6) Uani 1 1 d . . . . .
H19 H 0.4072 0.1727 0.7238 0.076 Uiso 1 1 calc R U . . .
C20 C 0.3706(3) 0.2137(3) 0.66085(6) 0.0530(5) Uani 1 1 d . . . . .
H20 H 0.4730 0.1346 0.6543 0.064 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 C9 1.136(2) . ?
N2 C19 1.321(3) . ?
N2 C18 1.326(3) . ?
C1 C2 1.377(2) . ?
C1 C6 1.389(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.367(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.390(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.461(2) . ?
C7 C8 1.347(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.440(2) . ?
C8 C10 1.483(2) . ?
C10 C11 1.382(2) . ?
C10 C15 1.394(2) . ?
C11 C12 1.374(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.390(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.382(2) . ?
C13 C16 1.481(2) . ?
C14 C15 1.380(2) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.380(3) . ?
C16 C20 1.383(3) . ?
C17 C18 1.376(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.375(3) . ?
C19 H19 0.9300 . ?
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
C19 N2 C18 115.24(17) . . ?
C2 C1 C6 121.06(17) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C3 C2 C1 120.37(18) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.78(18) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 120.35(19) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.76(18) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 117.63(16) . . ?
C1 C6 C7 124.34(15) . . ?
C5 C6 C7 118.00(15) . . ?
C8 C7 C6 129.64(16) . . ?
C8 C7 H7 115.2 . . ?
C6 C7 H7 115.2 . . ?
C7 C8 C9 119.63(15) . . ?
C7 C8 C10 124.69(15) . . ?
C9 C8 C10 115.61(14) . . ?
N1 C9 C8 178.0(2) . . ?
C11 C10 C15 117.11(16) . . ?
C11 C10 C8 121.93(15) . . ?
C15 C10 C8 120.96(15) . . ?
C12 C11 C10 121.49(17) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 121.59(17) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C14 C13 C12 117.15(16) . . ?
C14 C13 C16 121.87(15) . . ?
C12 C13 C16 120.97(16) . . ?
C15 C14 C13 121.38(16) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C10 121.28(16) . . ?
C14 C15 H15 119.4 . . ?
C10 C15 H15 119.4 . . ?
C17 C16 C20 116.00(16) . . ?
C17 C16 C13 121.74(16) . . ?
C20 C16 C13 122.26(16) . . ?
C18 C17 C16 119.96(19) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
N2 C18 C17 124.4(2) . . ?
N2 C18 H18 117.8 . . ?
C17 C18 H18 117.8 . . ?
N2 C19 C20 124.85(19) . . ?
N2 C19 H19 117.6 . . ?
C20 C19 H19 117.6 . . ?
C19 C20 C16 119.56(18) . . ?
C19 C20 H20 120.2 . . ?
C16 C20 H20 120.2 . . ?

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 0.0(3) . . . . ?
C1 C2 C3 C4 1.3(3) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C2 C1 C6 C5 -1.8(3) . . . . ?
C2 C1 C6 C7 -179.85(17) . . . . ?
C4 C5 C6 C1 2.2(3) . . . . ?
C4 C5 C6 C7 -179.58(18) . . . . ?
C1 C6 C7 C8 -28.7(3) . . . . ?
C5 C6 C7 C8 153.25(19) . . . . ?
C6 C7 C8 C9 -4.7(3) . . . . ?
C6 C7 C8 C10 178.57(16) . . . . ?
C7 C8 C10 C11 -8.1(3) . . . . ?
C9 C8 C10 C11 175.06(19) . . . . ?
C7 C8 C10 C15 172.07(17) . . . . ?
C9 C8 C10 C15 -4.8(2) . . . . ?
C15 C10 C11 C12 -0.4(3) . . . . ?
C8 C10 C11 C12 179.72(18) . . . . ?
C10 C11 C12 C13 0.1(3) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
C11 C12 C13 C16 179.33(19) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C16 C13 C14 C15 -179.02(16) . . . . ?
C13 C14 C15 C10 -0.7(3) . . . . ?
C11 C10 C15 C14 0.7(3) . . . . ?
C8 C10 C15 C14 -179.42(15) . . . . ?
C14 C13 C16 C17 143.5(2) . . . . ?
C12 C13 C16 C17 -35.8(3) . . . . ?
C14 C13 C16 C20 -36.0(3) . . . . ?
C12 C13 C16 C20 144.7(2) . . . . ?
C20 C16 C17 C18 0.0(3) . . . . ?
C13 C16 C17 C18 -179.55(19) . . . . ?
C19 N2 C18 C17 0.6(3) . . . . ?
C16 C17 C18 N2 -0.7(4) . . . . ?
C18 N2 C19 C20 0.1(3) . . . . ?
N2 C19 C20 C16 -0.8(3) . . . . ?
C17 C16 C20 C19 0.7(3) . . . . ?
C13 C16 C20 C19 -179.78(18) . . . . ?

_refine_diff_density_max         0.196
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.036

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_d8v19627
_database_code_depnum_ccdc_archive 'CCDC 2157130'
loop_
_audit_author_name
_audit_author_address
'Yipu Wang'
;East China University of Science and Technology
China
;
_audit_update_record             
;
2022-03-08 deposited with the CCDC.	2022-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H21 N5 O'
_chemical_formula_weight         491.54

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                   10.5108(4)
_cell_length_b                   17.0035(6)
_cell_length_c                   17.7169(9)
_cell_angle_alpha                63.8500(10)
_cell_angle_beta                 83.372(2)
_cell_angle_gamma                86.6710(10)
_cell_volume                     2823.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9906
_cell_measurement_theta_min      4.558
_cell_measurement_theta_max      53.428

_exptl_crystal_description       prismatic
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6503
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            40082
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.951
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             9911
_reflns_number_gt                6461
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1679P)²+0.5573P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.053(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         9911
_refine_ls_number_parameters     754
_refine_ls_number_restraints     96
_refine_ls_R_factor_all          0.1164
_refine_ls_R_factor_gt           0.0883
_refine_ls_wR_factor_ref         0.2924
_refine_ls_wR_factor_gt          0.2629
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.113
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.006 0.261 0.713 186 28 ' '
2 0.005 0.739 0.287 186 28 ' '
_platon_squeeze_details          
;
;


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 1.4902(4) 0.2744(2) 0.5659(2) 0.1040(11) Uani 1 1 d . . . . .
N2 N 0.8836(4) 0.6066(3) 0.1517(3) 0.1429(18) Uani 1 1 d . . . . .
N3 N 0.1758(4) 0.5364(2) -0.4799(2) 0.1095(12) Uani 1 1 d . . . . .
N4 N 0.1678(4) 0.7342(2) -0.3862(2) 0.1033(11) Uani 1 1 d . . . . .
N5 N 0.3849(3) 0.6831(2) -0.2322(2) 0.0987(10) Uani 1 1 d . . . . .
N6 N 1.3859(3) 0.7929(2) 1.04036(19) 0.0903(9) Uani 1 1 d . . . . .
N7 N 0.7882(5) 1.1039(4) 0.6084(3) 0.162(2) Uani 1 1 d . . . . .
N8 N 0.1344(3) 1.0775(2) -0.0415(2) 0.1055(11) Uani 1 1 d . . . . .
N9 N 0.1528(5) 1.2609(3) 0.0691(3) 0.1369(15) Uani 1 1 d . . . . .
N10 N 0.3433(4) 1.1941(3) 0.2267(3) 0.1181(13) Uani 1 1 d . . . . .
O1 O 0.3808(2) 0.46088(12) -0.32544(13) 0.0684(6) Uani 1 1 d . . . . .
O2 O 0.34842(19) 0.98845(12) 0.11332(12) 0.0638(5) Uani 1 1 d . . . . .
C1 C 1.4270(3) 0.2730(2) 0.44192(19) 0.0708(8) Uani 1 1 d . . . . .
H1 H 1.4428 0.2514 0.4018 0.085 Uiso 1 1 calc R U . . .
C2 C 1.5043(3) 0.2468(2) 0.5070(2) 0.0800(9) Uani 1 1 d . . . . .
H2 H 1.5703 0.2072 0.5092 0.096 Uiso 1 1 calc R U . . .
C3 C 1.3951(6) 0.3293(3) 0.5600(3) 0.1281(18) Uani 1 1 d . . . . .
H3 H 1.3824 0.3498 0.6011 0.154 Uiso 1 1 calc R U . . .
C4 C 1.3116(5) 0.3596(3) 0.4979(2) 0.1023(13) Uani 1 1 d . . . . .
H4 H 1.2463 0.3989 0.4981 0.123 Uiso 1 1 calc R U . . .
C5 C 1.3261(3) 0.33107(19) 0.43587(17) 0.0626(7) Uani 1 1 d . . . . .
C6 C 1.2384(3) 0.36202(18) 0.36844(16) 0.0575(7) Uani 1 1 d . . . . .
C7 C 1.1552(3) 0.4318(2) 0.35671(19) 0.0698(8) Uani 1 1 d . . . . .
H7 H 1.1540 0.4589 0.3924 0.084 Uiso 1 1 calc R U . . .
C8 C 1.0745(3) 0.4620(2) 0.2938(2) 0.0697(8) Uani 1 1 d . . . . .
H8 H 1.0207 0.5095 0.2872 0.084 Uiso 1 1 calc R U . . .
C9 C 1.0720(3) 0.42250(19) 0.23943(17) 0.0597(7) Uani 1 1 d . . . . .
C10 C 1.1537(3) 0.35222(19) 0.25152(17) 0.0636(7) Uani 1 1 d . . . . .
H10 H 1.1535 0.3242 0.2168 0.076 Uiso 1 1 calc R U . . .
C11 C 1.2356(3) 0.32281(19) 0.31417(17) 0.0640(8) Uani 1 1 d . . . . .
H11 H 1.2901 0.2757 0.3203 0.077 Uiso 1 1 calc R U . . .
C12 C 0.9815(3) 0.4564(2) 0.17330(17) 0.0614(7) Uani 1 1 d . . . . .
C13 C 0.9526(3) 0.4148(2) 0.12796(18) 0.0677(8) Uani 1 1 d . . . . .
H13 H 0.9959 0.3620 0.1401 0.081 Uiso 1 1 calc R U . . .
C14 C 0.8650(3) 0.4386(2) 0.06313(18) 0.0713(9) Uani 1 1 d . . . . .
C15 C 0.8617(4) 0.3849(2) 0.0242(2) 0.0841(10) Uani 1 1 d . . . . .
H15 H 0.9157 0.3362 0.0387 0.101 Uiso 1 1 calc R U . . .
C16 C 0.7763(4) 0.4031(3) -0.0383(2) 0.0910(12) Uani 1 1 d . . . . .
H16 H 0.7738 0.3668 -0.0649 0.109 Uiso 1 1 calc R U . . .
C17 C 0.6953(3) 0.4773(3) -0.0593(2) 0.0829(10) Uani 1 1 d . . . . .
C18 C 0.7041(4) 0.5322(3) -0.0238(3) 0.0974(12) Uani 1 1 d . . . . .
H18 H 0.6551 0.5833 -0.0407 0.117 Uiso 1 1 calc R U . . .
C19 C 0.7841(4) 0.5129(3) 0.0361(2) 0.0934(11) Uani 1 1 d . . . . .
H19 H 0.7861 0.5507 0.0611 0.112 Uiso 1 1 calc R U . . .
C20 C 0.6025(4) 0.4995(3) -0.1240(2) 0.0884(10) Uani 1 1 d . . . . .
H20 H 0.5582 0.5523 -0.1381 0.106 Uiso 1 1 calc R U . . .
C21 C 0.5776(4) 0.4556(3) -0.1610(2) 0.0897(11) Uani 1 1 d . . . . .
H21 H 0.6202 0.4021 -0.1458 0.108 Uiso 1 1 calc R U . . .
C22 C 0.4885(3) 0.4786(2) -0.22620(18) 0.0669(8) Uani 1 1 d . . . . .
C23 C 0.4745(3) 0.4153(2) -0.26295(19) 0.0692(8) Uani 1 1 d . . . . .
C24 C 0.3440(3) 0.53678(18) -0.32478(17) 0.0604(7) Uani 1 1 d . . . . .
C25 C 0.4096(3) 0.5488(2) -0.26341(18) 0.0634(7) Uani 1 1 d . . . . .
C26 C 0.3942(3) 0.6241(2) -0.2468(2) 0.0739(9) Uani 1 1 d . . . . .
C27 C 0.2577(3) 0.58769(18) -0.37878(18) 0.0639(7) Uani 1 1 d . . . . .
C28 C 0.2115(3) 0.5600(2) -0.4352(2) 0.0756(9) Uani 1 1 d . . . . .
C29 C 0.2094(3) 0.6690(2) -0.3816(2) 0.0725(8) Uani 1 1 d . . . . .
C30 C 0.4145(3) 0.3298(2) -0.1996(2) 0.0842(10) Uani 1 1 d . . . . .
H30A H 0.3373 0.3413 -0.1714 0.126 Uiso 1 1 calc R U . . .
H30B H 0.4734 0.2973 -0.1588 0.126 Uiso 1 1 calc R U . . .
H30C H 0.3947 0.2962 -0.2283 0.126 Uiso 1 1 calc R U . . .
C31 C 0.5954(3) 0.4035(3) -0.3115(2) 0.0877(10) Uani 1 1 d . . . . .
H31A H 0.5780 0.3681 -0.3389 0.132 Uiso 1 1 calc R U . . .
H31B H 0.6594 0.3752 -0.2734 0.132 Uiso 1 1 calc R U . . .
H31C H 0.6259 0.4598 -0.3533 0.132 Uiso 1 1 calc R U . . .
C32 C 0.9244(4) 0.5393(3) 0.1602(2) 0.0883(11) Uani 1 1 d . . . . .
C33 C 1.3465(3) 0.80320(19) 0.90587(19) 0.0678(8) Uani 1 1 d . . . . .
H33 H 1.3742 0.7898 0.8611 0.081 Uiso 1 1 calc R U . . .
C34 C 1.4191(3) 0.7772(2) 0.9742(2) 0.0802(10) Uani 1 1 d . . . . .
H34 H 1.4954 0.7470 0.9730 0.096 Uiso 1 1 calc R U . . .
C35 C 1.2779(4) 0.8364(3) 1.0385(2) 0.0953(12) Uani 1 1 d . . . . .
H35 H 1.2524 0.8487 1.0842 0.114 Uiso 1 1 calc R U . . .
C36 C 1.1997(4) 0.8652(2) 0.97438(19) 0.0770(9) Uani 1 1 d . . . . .
H36 H 1.1243 0.8956 0.9776 0.092 Uiso 1 1 calc R U . . .
C37 C 1.2338(3) 0.84866(17) 0.90499(17) 0.0584(7) Uani 1 1 d . . . . .
C38 C 1.1524(3) 0.87858(18) 0.83435(16) 0.0570(7) Uani 1 1 d . . . . .
C39 C 1.1486(3) 0.8319(2) 0.78653(19) 0.0694(8) Uani 1 1 d . . . . .
H39 H 1.1993 0.7820 0.7986 0.083 Uiso 1 1 calc R U . . .
C40 C 1.0715(3) 0.8583(2) 0.72233(19) 0.0750(9) Uani 1 1 d . . . . .
H40 H 1.0702 0.8256 0.6920 0.090 Uiso 1 1 calc R U . . .
C41 C 0.9953(3) 0.9329(2) 0.70152(16) 0.0612(7) Uani 1 1 d . . . . .
C42 C 1.0009(3) 0.9798(2) 0.74853(18) 0.0668(8) Uani 1 1 d . . . . .
H42 H 0.9515 1.0304 0.7356 0.080 Uiso 1 1 calc R U . . .
C43 C 1.0770(3) 0.95365(19) 0.81323(17) 0.0649(8) Uani 1 1 d . . . . .
H43 H 1.0782 0.9865 0.8434 0.078 Uiso 1 1 calc R U . . .
C44 C 0.9114(3) 0.9627(2) 0.63201(17) 0.0702(8) Uani 1 1 d . . . . .
C45 C 0.8968(4) 0.9194(3) 0.5860(2) 0.0860(11) Uani 1 1 d . . . . .
C46 C 0.8148(8) 0.9520(5) 0.5153(4) 0.0828(15) Uani 0.6 1 d . U P A 1
C47 C 0.8091(7) 0.8980(5) 0.4768(4) 0.0833(15) Uani 0.6 1 d . U P A 1
H47 H 0.8585 0.8470 0.4944 0.100 Uiso 0.6 1 calc R U P A 1
C48 C 0.7322(7) 0.9170(4) 0.4124(4) 0.0802(14) Uani 0.6 1 d . U P A 1
H48 H 0.7313 0.8794 0.3870 0.096 Uiso 0.6 1 calc R U P A 1
C49 C 0.6559(7) 0.9926(4) 0.3856(4) 0.0851(13) Uani 0.6 1 d . U P A 1
C50 C 0.6724(7) 1.0504(5) 0.4150(4) 0.1026(15) Uani 0.6 1 d . U P A 1
H50 H 0.6295 1.1039 0.3927 0.123 Uiso 0.6 1 calc R U P A 1
C51 C 0.7507(7) 1.0336(5) 0.4774(4) 0.1023(16) Uani 0.6 1 d . U P A 1
H51 H 0.7618 1.0766 0.4950 0.123 Uiso 0.6 1 calc R U P A 1
C52 C 0.5678(6) 1.0145(4) 0.3205(4) 0.0804(13) Uani 0.6 1 d . U P A 1
H52 H 0.5271 1.0688 0.3036 0.097 Uiso 0.6 1 calc R U P A 1
C53 C 0.5391(9) 0.9668(5) 0.2830(5) 0.0738(17) Uani 0.6 1 d . U P A 1
H53 H 0.5749 0.9112 0.2989 0.089 Uiso 0.6 1 calc R U P A 1
C46' C 0.8175(7) 0.9203(5) 0.5199(4) 0.081(2) Uani 0.4 1 d G U P A 2
C47' C 0.8486(6) 0.8678(4) 0.4784(5) 0.0736(19) Uani 0.4 1 d G U P A 2
H47' H 0.9146 0.8267 0.4951 0.088 Uiso 0.4 1 calc R U P A 2
C48' C 0.7812(6) 0.8767(4) 0.4120(4) 0.0726(17) Uani 0.4 1 d G U P A 2
H48' H 0.8020 0.8415 0.3843 0.087 Uiso 0.4 1 calc R U P A 2
C49' C 0.6827(6) 0.9381(5) 0.3870(4) 0.0745(16) Uani 0.4 1 d G U P A 2
C50' C 0.6516(6) 0.9906(4) 0.4285(4) 0.091(2) Uani 0.4 1 d G U P A 2
H50' H 0.5856 1.0317 0.4118 0.109 Uiso 0.4 1 calc R U P A 2
C51' C 0.7190(7) 0.9817(4) 0.4949(4) 0.093(2) Uani 0.4 1 d G U P A 2
H51' H 0.6981 1.0168 0.5226 0.112 Uiso 0.4 1 calc R U P A 2
C52' C 0.6109(8) 0.9417(5) 0.3184(5) 0.0675(15) Uani 0.4 1 d . U P A 2
H52' H 0.6272 0.8983 0.2999 0.081 Uiso 0.4 1 calc R U P A 2
C53' C 0.5249(11) 1.0030(7) 0.2818(7) 0.065(2) Uani 0.4 1 d . U P A 2
H53' H 0.5102 1.0486 0.2972 0.078 Uiso 0.4 1 calc R U P A 2
C54 C 0.4523(3) 1.0000(2) 0.21708(17) 0.0658(8) Uani 1 1 d . . . . .
C55 C 0.4422(3) 0.94080(19) 0.17511(17) 0.0619(7) Uani 1 1 d . . . . .
C56 C 0.3113(3) 1.06273(18) 0.11736(17) 0.0572(7) Uani 1 1 d . . . . .
C57 C 0.3736(3) 1.07002(19) 0.18243(17) 0.0624(7) Uani 1 1 d . . . . .
C58 C 0.3549(3) 1.1399(2) 0.2062(2) 0.0790(9) Uani 1 1 d . . . . .
C59 C 0.2278(3) 1.11727(19) 0.06419(18) 0.0653(8) Uani 1 1 d . . . . .
C60 C 0.1768(3) 1.0952(2) 0.0054(2) 0.0757(9) Uani 1 1 d . . . . .
C61 C 0.1860(4) 1.1976(2) 0.0659(2) 0.0883(10) Uani 1 1 d . . . . .
C62 C 0.3825(4) 0.8533(2) 0.2352(2) 0.0802(9) Uani 1 1 d . . . . .
H62A H 0.3029 0.8629 0.2625 0.120 Uiso 1 1 calc R U . . .
H62B H 0.4397 0.8204 0.2770 0.120 Uiso 1 1 calc R U . . .
H62C H 0.3671 0.8213 0.2041 0.120 Uiso 1 1 calc R U . . .
C63 C 0.5634(3) 0.9331(3) 0.1246(2) 0.0849(10) Uani 1 1 d . . . . .
H63A H 0.5462 0.9022 0.0928 0.127 Uiso 1 1 calc R U . . .
H63B H 0.6269 0.9017 0.1621 0.127 Uiso 1 1 calc R U . . .
H63C H 0.5944 0.9906 0.0865 0.127 Uiso 1 1 calc R U . . .
C64 C 0.8427(4) 1.0414(3) 0.6171(2) 0.0985(13) Uani 1 1 d . . . . .
H45 H 0.938(4) 0.865(3) 0.605(3) 0.101(13) Uiso 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 C3 1.309(6) . ?
N1 C2 1.312(5) . ?
N2 C32 1.149(5) . ?
N3 C28 1.140(4) . ?
N4 C29 1.141(4) . ?
N5 C26 1.137(4) . ?
N6 C35 1.314(5) . ?
N6 C34 1.318(5) . ?
N7 C64 1.133(5) . ?
N8 C60 1.141(4) . ?
N9 C61 1.135(4) . ?
N10 C58 1.127(4) . ?
O1 C24 1.330(3) . ?
O1 C23 1.484(3) . ?
O2 C56 1.330(3) . ?
O2 C55 1.483(3) . ?
C1 C2 1.382(4) . ?
C1 C5 1.387(4) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 C4 1.384(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.483(4) . ?
C6 C7 1.385(4) . ?
C6 C11 1.394(4) . ?
C7 C8 1.375(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.399(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.382(4) . ?
C9 C12 1.486(4) . ?
C10 C11 1.380(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.349(4) . ?
C12 C32 1.432(5) . ?
C13 C14 1.457(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.371(5) . ?
C14 C19 1.408(5) . ?
C15 C16 1.422(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.410(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.347(5) . ?
C17 C20 1.498(5) . ?
C18 C19 1.345(5) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.246(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.474(5) . ?
C21 H21 0.9300 . ?
C22 C25 1.367(4) . ?
C22 C23 1.503(4) . ?
C23 C31 1.506(5) . ?
C23 C30 1.509(5) . ?
C24 C27 1.366(4) . ?
C24 C25 1.444(4) . ?
C25 C26 1.431(4) . ?
C27 C28 1.417(4) . ?
C27 C29 1.426(4) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C33 C37 1.374(4) . ?
C33 C34 1.395(4) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C35 C36 1.373(5) . ?
C35 H35 0.9300 . ?
C36 C37 1.382(4) . ?
C36 H36 0.9300 . ?
C37 C38 1.481(4) . ?
C38 C43 1.389(4) . ?
C38 C39 1.398(4) . ?
C39 C40 1.368(4) . ?
C39 H39 0.9300 . ?
C40 C41 1.387(4) . ?
C40 H40 0.9300 . ?
C41 C42 1.391(4) . ?
C41 C44 1.483(4) . ?
C42 C43 1.368(4) . ?
C42 H42 0.9300 . ?
C43 H43 0.9300 . ?
C44 C45 1.342(5) . ?
C44 C64 1.416(6) . ?
C45 C46 1.484(7) . ?
C45 C46' 1.509(6) . ?
C45 H45 0.93(4) . ?
C46 C47 1.372(9) . ?
C46 C51 1.415(10) . ?
C47 C48 1.384(9) . ?
C47 H47 0.9300 . ?
C48 C49 1.397(9) . ?
C48 H48 0.9300 . ?
C49 C50 1.327(9) . ?
C49 C52 1.468(8) . ?
C50 C51 1.372(9) . ?
C50 H50 0.9300 . ?
C51 H51 0.9300 . ?
C52 C53 1.317(9) . ?
C52 H52 0.9300 . ?
C53 C54 1.456(9) . ?
C53 H53 0.9300 . ?
C46' C47' 1.3900 . ?
C46' C51' 1.3900 . ?
C47' C48' 1.3900 . ?
C47' H47' 0.9300 . ?
C48' C49' 1.3900 . ?
C48' H48' 0.9300 . ?
C49' C50' 1.3900 . ?
C49' C52' 1.481(9) . ?
C50' C51' 1.3900 . ?
C50' H50' 0.9300 . ?
C51' H51' 0.9300 . ?
C52' C53' 1.325(14) . ?
C52' H52' 0.9300 . ?
C53' C54 1.468(12) . ?
C53' H53' 0.9300 . ?
C54 C57 1.355(4) . ?
C54 C55 1.505(4) . ?
C55 C63 1.504(4) . ?
C55 C62 1.516(4) . ?
C56 C59 1.357(4) . ?
C56 C57 1.444(4) . ?
C57 C58 1.422(4) . ?
C59 C60 1.418(5) . ?
C59 C61 1.423(5) . ?
C62 H62A 0.9600 . ?
C62 H62B 0.9600 . ?
C62 H62C 0.9600 . ?
C63 H63A 0.9600 . ?
C63 H63B 0.9600 . ?
C63 H63C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C2 115.2(3) . . ?
C35 N6 C34 115.6(3) . . ?
C24 O1 C23 110.7(2) . . ?
C56 O2 C55 110.7(2) . . ?
C2 C1 C5 120.7(3) . . ?
C2 C1 H1 119.7 . . ?
C5 C1 H1 119.7 . . ?
N1 C2 C1 124.0(3) . . ?
N1 C2 H2 118.0 . . ?
C1 C2 H2 118.0 . . ?
N1 C3 C4 125.7(4) . . ?
N1 C3 H3 117.1 . . ?
C4 C3 H3 117.1 . . ?
C5 C4 C3 119.4(4) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C1 115.1(3) . . ?
C4 C5 C6 120.8(3) . . ?
C1 C5 C6 124.1(3) . . ?
C7 C6 C11 117.0(3) . . ?
C7 C6 C5 121.0(2) . . ?
C11 C6 C5 122.0(3) . . ?
C8 C7 C6 121.7(3) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C7 C8 C9 121.1(3) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C10 C9 C8 117.4(3) . . ?
C10 C9 C12 123.4(3) . . ?
C8 C9 C12 119.2(3) . . ?
C11 C10 C9 121.3(3) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C6 121.5(3) . . ?
C10 C11 H11 119.2 . . ?
C6 C11 H11 119.2 . . ?
C13 C12 C32 120.9(3) . . ?
C13 C12 C9 124.8(3) . . ?
C32 C12 C9 114.4(3) . . ?
C12 C13 C14 130.9(3) . . ?
C12 C13 H13 114.5 . . ?
C14 C13 H13 114.5 . . ?
C15 C14 C19 116.9(3) . . ?
C15 C14 C13 117.4(3) . . ?
C19 C14 C13 125.7(3) . . ?
C14 C15 C16 120.4(4) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C17 C16 C15 118.8(4) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C18 C17 C16 120.3(3) . . ?
C18 C17 C20 118.4(4) . . ?
C16 C17 C20 121.3(4) . . ?
C19 C18 C17 119.7(4) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C14 123.7(4) . . ?
C18 C19 H19 118.1 . . ?
C14 C19 H19 118.1 . . ?
C21 C20 C17 127.7(4) . . ?
C21 C20 H20 116.2 . . ?
C17 C20 H20 116.2 . . ?
C20 C21 C22 127.6(4) . . ?
C20 C21 H21 116.2 . . ?
C22 C21 H21 116.2 . . ?
C25 C22 C21 133.3(3) . . ?
C25 C22 C23 108.4(2) . . ?
C21 C22 C23 118.3(3) . . ?
O1 C23 C22 102.5(2) . . ?
O1 C23 C31 106.8(2) . . ?
C22 C23 C31 113.3(3) . . ?
O1 C23 C30 106.8(2) . . ?
C22 C23 C30 113.2(3) . . ?
C31 C23 C30 113.2(3) . . ?
O1 C24 C27 118.7(2) . . ?
O1 C24 C25 109.1(2) . . ?
C27 C24 C25 132.2(3) . . ?
C22 C25 C26 126.5(3) . . ?
C22 C25 C24 109.2(3) . . ?
C26 C25 C24 124.3(3) . . ?
N5 C26 C25 178.0(4) . . ?
C24 C27 C28 119.9(3) . . ?
C24 C27 C29 123.2(3) . . ?
C28 C27 C29 116.9(3) . . ?
N3 C28 C27 178.7(4) . . ?
N4 C29 C27 177.4(4) . . ?
C23 C30 H30A 109.5 . . ?
C23 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C23 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C23 C31 H31A 109.5 . . ?
C23 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C23 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N2 C32 C12 176.4(4) . . ?
C37 C33 C34 119.7(3) . . ?
C37 C33 H33 120.1 . . ?
C34 C33 H33 120.1 . . ?
N6 C34 C33 123.8(3) . . ?
N6 C34 H34 118.1 . . ?
C33 C34 H34 118.1 . . ?
N6 C35 C36 125.2(4) . . ?
N6 C35 H35 117.4 . . ?
C36 C35 H35 117.4 . . ?
C35 C36 C37 119.4(3) . . ?
C35 C36 H36 120.3 . . ?
C37 C36 H36 120.3 . . ?
C33 C37 C36 116.2(3) . . ?
C33 C37 C38 122.6(3) . . ?
C36 C37 C38 121.2(3) . . ?
C43 C38 C39 117.5(2) . . ?
C43 C38 C37 121.4(2) . . ?
C39 C38 C37 121.0(3) . . ?
C40 C39 C38 121.2(3) . . ?
C40 C39 H39 119.4 . . ?
C38 C39 H39 119.4 . . ?
C39 C40 C41 121.4(3) . . ?
C39 C40 H40 119.3 . . ?
C41 C40 H40 119.3 . . ?
C40 C41 C42 117.1(3) . . ?
C40 C41 C44 122.2(3) . . ?
C42 C41 C44 120.7(3) . . ?
C43 C42 C41 122.0(3) . . ?
C43 C42 H42 119.0 . . ?
C41 C42 H42 119.0 . . ?
C42 C43 C38 120.8(3) . . ?
C42 C43 H43 119.6 . . ?
C38 C43 H43 119.6 . . ?
C45 C44 C64 120.5(3) . . ?
C45 C44 C41 124.3(3) . . ?
C64 C44 C41 115.2(3) . . ?
C44 C45 C46 123.1(5) . . ?
C44 C45 C46' 141.4(5) . . ?
C44 C45 H45 114(3) . . ?
C46 C45 H45 123(3) . . ?
C46' C45 H45 104(3) . . ?
C47 C46 C51 115.4(5) . . ?
C47 C46 C45 114.9(6) . . ?
C51 C46 C45 129.5(6) . . ?
C46 C47 C48 122.1(7) . . ?
C46 C47 H47 119.0 . . ?
C48 C47 H47 119.0 . . ?
C47 C48 C49 120.0(6) . . ?
C47 C48 H48 120.0 . . ?
C49 C48 H48 120.0 . . ?
C50 C49 C48 118.2(6) . . ?
C50 C49 C52 118.8(6) . . ?
C48 C49 C52 122.8(6) . . ?
C49 C50 C51 122.1(7) . . ?
C49 C50 H50 118.9 . . ?
C51 C50 H50 118.9 . . ?
C50 C51 C46 121.1(7) . . ?
C50 C51 H51 119.4 . . ?
C46 C51 H51 119.4 . . ?
C53 C52 C49 128.1(7) . . ?
C53 C52 H52 115.9 . . ?
C49 C52 H52 115.9 . . ?
C52 C53 C54 121.1(7) . . ?
C52 C53 H53 119.5 . . ?
C54 C53 H53 119.5 . . ?
C47' C46' C51' 120.0 . . ?
C47' C46' C45 121.6(5) . . ?
C51' C46' C45 118.1(4) . . ?
C46' C47' C48' 120.0 . . ?
C46' C47' H47' 120.0 . . ?
C48' C47' H47' 120.0 . . ?
C49' C48' C47' 120.0 . . ?
C49' C48' H48' 120.0 . . ?
C47' C48' H48' 120.0 . . ?
C48' C49' C50' 120.0 . . ?
C48' C49' C52' 117.3(5) . . ?
C50' C49' C52' 122.6(5) . . ?
C51' C50' C49' 120.0 . . ?
C51' C50' H50' 120.0 . . ?
C49' C50' H50' 120.0 . . ?
C50' C51' C46' 120.0 . . ?
C50' C51' H51' 120.0 . . ?
C46' C51' H51' 120.0 . . ?
C53' C52' C49' 123.8(8) . . ?
C53' C52' H52' 118.1 . . ?
C49' C52' H52' 118.1 . . ?
C52' C53' C54 121.0(9) . . ?
C52' C53' H53' 119.5 . . ?
C54 C53' H53' 119.5 . . ?
C57 C54 C53 137.8(4) . . ?
C57 C54 C53' 113.6(5) . . ?
C57 C54 C55 108.7(2) . . ?
C53 C54 C55 113.5(4) . . ?
C53' C54 C55 137.7(5) . . ?
O2 C55 C63 106.4(2) . . ?
O2 C55 C54 102.3(2) . . ?
C63 C55 C54 114.2(3) . . ?
O2 C55 C62 106.6(2) . . ?
C63 C55 C62 113.7(3) . . ?
C54 C55 C62 112.5(2) . . ?
O2 C56 C59 119.9(2) . . ?
O2 C56 C57 109.1(2) . . ?
C59 C56 C57 131.0(3) . . ?
C54 C57 C58 125.6(3) . . ?
C54 C57 C56 109.3(2) . . ?
C58 C57 C56 125.1(3) . . ?
N10 C58 C57 177.8(4) . . ?
C56 C59 C60 120.9(3) . . ?
C56 C59 C61 121.9(3) . . ?
C60 C59 C61 117.2(3) . . ?
N8 C60 C59 179.2(4) . . ?
N9 C61 C59 178.6(4) . . ?
C55 C62 H62A 109.5 . . ?
C55 C62 H62B 109.5 . . ?
H62A C62 H62B 109.5 . . ?
C55 C62 H62C 109.5 . . ?
H62A C62 H62C 109.5 . . ?
H62B C62 H62C 109.5 . . ?
C55 C63 H63A 109.5 . . ?
C55 C63 H63B 109.5 . . ?
H63A C63 H63B 109.5 . . ?
C55 C63 H63C 109.5 . . ?
H63A C63 H63C 109.5 . . ?
H63B C63 H63C 109.5 . . ?
N7 C64 C44 177.3(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
C3 N1 C2 C1 0.6(6) . . . . ?
C5 C1 C2 N1 -0.7(5) . . . . ?
C2 N1 C3 C4 -0.3(8) . . . . ?
N1 C3 C4 C5 0.2(8) . . . . ?
C3 C4 C5 C1 -0.3(6) . . . . ?
C3 C4 C5 C6 179.9(4) . . . . ?
C2 C1 C5 C4 0.5(5) . . . . ?
C2 C1 C5 C6 -179.7(3) . . . . ?
C4 C5 C6 C7 11.9(5) . . . . ?
C1 C5 C6 C7 -167.9(3) . . . . ?
C4 C5 C6 C11 -168.1(3) . . . . ?
C1 C5 C6 C11 12.1(5) . . . . ?
C11 C6 C7 C8 -0.8(5) . . . . ?
C5 C6 C7 C8 179.1(3) . . . . ?
C6 C7 C8 C9 0.8(5) . . . . ?
C7 C8 C9 C10 -0.1(5) . . . . ?
C7 C8 C9 C12 178.9(3) . . . . ?
C8 C9 C10 C11 -0.7(4) . . . . ?
C12 C9 C10 C11 -179.6(3) . . . . ?
C9 C10 C11 C6 0.7(5) . . . . ?
C7 C6 C11 C10 0.1(4) . . . . ?
C5 C6 C11 C10 -179.9(3) . . . . ?
C10 C9 C12 C13 11.9(5) . . . . ?
C8 C9 C12 C13 -167.0(3) . . . . ?
C10 C9 C12 C32 -168.2(3) . . . . ?
C8 C9 C12 C32 12.9(4) . . . . ?
C32 C12 C13 C14 -1.3(5) . . . . ?
C9 C12 C13 C14 178.6(3) . . . . ?
C12 C13 C14 C15 176.1(3) . . . . ?
C12 C13 C14 C19 -3.1(6) . . . . ?
C19 C14 C15 C16 -2.2(5) . . . . ?
C13 C14 C15 C16 178.5(3) . . . . ?
C14 C15 C16 C17 0.0(5) . . . . ?
C15 C16 C17 C18 3.5(5) . . . . ?
C15 C16 C17 C20 -179.4(3) . . . . ?
C16 C17 C18 C19 -4.7(6) . . . . ?
C20 C17 C18 C19 178.2(4) . . . . ?
C17 C18 C19 C14 2.4(6) . . . . ?
C15 C14 C19 C18 1.1(6) . . . . ?
C13 C14 C19 C18 -179.7(3) . . . . ?
C18 C17 C20 C21 -177.1(4) . . . . ?
C16 C17 C20 C21 5.8(6) . . . . ?
C17 C20 C21 C22 -178.4(3) . . . . ?
C20 C21 C22 C25 -0.9(6) . . . . ?
C20 C21 C22 C23 179.5(4) . . . . ?
C24 O1 C23 C22 -1.0(3) . . . . ?
C24 O1 C23 C31 -120.4(3) . . . . ?
C24 O1 C23 C30 118.2(3) . . . . ?
C25 C22 C23 O1 1.1(3) . . . . ?
C21 C22 C23 O1 -179.2(3) . . . . ?
C25 C22 C23 C31 115.8(3) . . . . ?
C21 C22 C23 C31 -64.5(4) . . . . ?
C25 C22 C23 C30 -113.5(3) . . . . ?
C21 C22 C23 C30 66.1(4) . . . . ?
C23 O1 C24 C27 179.9(3) . . . . ?
C23 O1 C24 C25 0.5(3) . . . . ?
C21 C22 C25 C26 0.7(6) . . . . ?
C23 C22 C25 C26 -179.7(3) . . . . ?
C21 C22 C25 C24 179.5(3) . . . . ?
C23 C22 C25 C24 -0.9(3) . . . . ?
O1 C24 C25 C22 0.3(3) . . . . ?
C27 C24 C25 C22 -179.0(3) . . . . ?
O1 C24 C25 C26 179.1(3) . . . . ?
C27 C24 C25 C26 -0.2(5) . . . . ?
O1 C24 C27 C28 -1.3(5) . . . . ?
C25 C24 C27 C28 177.8(3) . . . . ?
O1 C24 C27 C29 178.3(3) . . . . ?
C25 C24 C27 C29 -2.5(5) . . . . ?
C35 N6 C34 C33 -0.6(5) . . . . ?
C37 C33 C34 N6 0.6(5) . . . . ?
C34 N6 C35 C36 0.4(6) . . . . ?
N6 C35 C36 C37 -0.2(6) . . . . ?
C34 C33 C37 C36 -0.4(4) . . . . ?
C34 C33 C37 C38 179.7(3) . . . . ?
C35 C36 C37 C33 0.2(5) . . . . ?
C35 C36 C37 C38 -179.9(3) . . . . ?
C33 C37 C38 C43 -150.1(3) . . . . ?
C36 C37 C38 C43 30.0(4) . . . . ?
C33 C37 C38 C39 30.1(4) . . . . ?
C36 C37 C38 C39 -149.8(3) . . . . ?
C43 C38 C39 C40 -1.2(5) . . . . ?
C37 C38 C39 C40 178.7(3) . . . . ?
C38 C39 C40 C41 0.7(5) . . . . ?
C39 C40 C41 C42 0.2(5) . . . . ?
C39 C40 C41 C44 179.8(3) . . . . ?
C40 C41 C42 C43 -0.7(5) . . . . ?
C44 C41 C42 C43 179.7(3) . . . . ?
C41 C42 C43 C38 0.2(5) . . . . ?
C39 C38 C43 C42 0.7(4) . . . . ?
C37 C38 C43 C42 -179.1(3) . . . . ?
C40 C41 C44 C45 3.2(5) . . . . ?
C42 C41 C44 C45 -177.3(3) . . . . ?
C40 C41 C44 C64 -178.1(3) . . . . ?
C42 C41 C44 C64 1.4(4) . . . . ?
C64 C44 C45 C46 3.0(6) . . . . ?
C41 C44 C45 C46 -178.3(5) . . . . ?
C64 C44 C45 C46' -6.6(8) . . . . ?
C41 C44 C45 C46' 172.0(6) . . . . ?
C44 C45 C46 C47 -178.5(5) . . . . ?
C46' C45 C46 C47 -16.7(14) . . . . ?
C44 C45 C46 C51 7.5(11) . . . . ?
C46' C45 C46 C51 169(2) . . . . ?
C51 C46 C47 C48 -8.2(10) . . . . ?
C45 C46 C47 C48 176.9(6) . . . . ?
C46 C47 C48 C49 -0.9(10) . . . . ?
C47 C48 C49 C50 8.9(10) . . . . ?
C47 C48 C49 C52 -177.1(6) . . . . ?
C48 C49 C50 C51 -7.5(11) . . . . ?
C52 C49 C50 C51 178.3(7) . . . . ?
C49 C50 C51 C46 -2.0(12) . . . . ?
C47 C46 C51 C50 9.8(11) . . . . ?
C45 C46 C51 C50 -176.2(7) . . . . ?
C50 C49 C52 C53 179.5(8) . . . . ?
C48 C49 C52 C53 5.6(12) . . . . ?
C49 C52 C53 C54 -177.9(6) . . . . ?
C44 C45 C46' C47' 170.0(5) . . . . ?
C46 C45 C46' C47' 145.2(19) . . . . ?
C44 C45 C46' C51' -3.7(9) . . . . ?
C46 C45 C46' C51' -28.4(14) . . . . ?
C51' C46' C47' C48' 0.0 . . . . ?
C45 C46' C47' C48' -173.5(7) . . . . ?
C46' C47' C48' C49' 0.0 . . . . ?
C47' C48' C49' C50' 0.0 . . . . ?
C47' C48' C49' C52' -177.4(6) . . . . ?
C48' C49' C50' C51' 0.0 . . . . ?
C52' C49' C50' C51' 177.3(7) . . . . ?
C49' C50' C51' C46' 0.0 . . . . ?
C47' C46' C51' C50' 0.0 . . . . ?
C45 C46' C51' C50' 173.8(6) . . . . ?
C48' C49' C52' C53' -172.1(8) . . . . ?
C50' C49' C52' C53' 10.6(11) . . . . ?
C49' C52' C53' C54 -176.7(7) . . . . ?
C52 C53 C54 C57 -7.9(11) . . . . ?
C52 C53 C54 C53' -1.1(12) . . . . ?
C52 C53 C54 C55 173.7(6) . . . . ?
C52' C53' C54 C57 -176.4(8) . . . . ?
C52' C53' C54 C53 8.6(10) . . . . ?
C52' C53' C54 C55 1.5(14) . . . . ?
C56 O2 C55 C63 -119.4(3) . . . . ?
C56 O2 C55 C54 0.7(3) . . . . ?
C56 O2 C55 C62 118.9(3) . . . . ?
C57 C54 C55 O2 0.2(3) . . . . ?
C53 C54 C55 O2 179.1(4) . . . . ?
C53' C54 C55 O2 -177.7(7) . . . . ?
C57 C54 C55 C63 114.7(3) . . . . ?
C53 C54 C55 C63 -66.4(5) . . . . ?
C53' C54 C55 C63 -63.2(8) . . . . ?
C57 C54 C55 C62 -113.7(3) . . . . ?
C53 C54 C55 C62 65.2(5) . . . . ?
C53' C54 C55 C62 68.4(8) . . . . ?
C55 O2 C56 C59 178.3(3) . . . . ?
C55 O2 C56 C57 -1.3(3) . . . . ?
C53 C54 C57 C58 0.4(7) . . . . ?
C53' C54 C57 C58 -2.6(6) . . . . ?
C55 C54 C57 C58 178.9(3) . . . . ?
C53 C54 C57 C56 -179.5(6) . . . . ?
C53' C54 C57 C56 177.5(5) . . . . ?
C55 C54 C57 C56 -1.0(3) . . . . ?
O2 C56 C57 C54 1.4(3) . . . . ?
C59 C56 C57 C54 -178.1(3) . . . . ?
O2 C56 C57 C58 -178.5(3) . . . . ?
C59 C56 C57 C58 2.0(5) . . . . ?
O2 C56 C59 C60 1.6(4) . . . . ?
C57 C56 C59 C60 -179.0(3) . . . . ?
O2 C56 C59 C61 -179.6(3) . . . . ?
C57 C56 C59 C61 -0.2(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C62 H62B N1 0.96 2.70 3.595(4) 156.2 2_766
C62 H62A N7 0.96 2.65 3.451(6) 140.9 2_676
C30 H30B N6 0.96 2.56 3.519(4) 175.1 2_766
C30 H30A N2 0.96 2.48 3.394(6) 159.1 2_665
C4 H4 N3 0.93 2.59 3.412(5) 147.8 1_656

_refine_diff_density_max         0.824
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.067

_shelxl_version_number           2013-4

