# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_2w8_a
_database_code_depnum_ccdc_archive 'CCDC 2190896'
loop_
_audit_author_name
_audit_author_address
'yoshifumi hashikawa'
;ICR, Kyoto Univ
Japan
;
_audit_update_record             
;
2023-01-11 deposited with the CCDC.	2023-01-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H21.65 N O0.32'
_chemical_formula_weight         617.47

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           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'

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

_cell_length_a                   11.7831(12)
_cell_length_b                   16.8231(17)
_cell_length_c                   14.2431(14)
_cell_angle_alpha                90
_cell_angle_beta                 94.160(2)
_cell_angle_gamma                90
_cell_volume                     2815.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4631
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      25.00

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_F_000             1277
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Smart APEX II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13832
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.876
_diffrn_reflns_theta_max         25.037
_diffrn_reflns_theta_full        25.037
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5149
_reflns_number_gt                4225
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0657P)²+0.9765P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5149
_refine_ls_number_parameters     529
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1223
_refine_ls_wR_factor_gt          0.1135
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.186
_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
C1 C 1.04848(14) 0.71101(10) 0.79823(11) 0.0199(4) Uani 1 1 d . . . . .
H1 H 1.101561 0.683495 0.839816 0.024 Uiso 1 1 calc R U . . .
C2 C 0.96651(13) 0.66399(10) 0.73400(11) 0.0187(4) Uani 1 1 d . . . . .
C3 C 0.91717(13) 0.70920(9) 0.64915(11) 0.0178(3) Uani 1 1 d . . . . .
C4 C 0.83532(13) 0.66604(9) 0.58822(11) 0.0174(3) Uani 1 1 d . . . . .
C5 C 0.78706(14) 0.70695(10) 0.51019(11) 0.0184(4) Uani 1 1 d . . . . .
C6 C 0.68371(14) 0.68082(10) 0.45903(11) 0.0199(4) Uani 1 1 d . . . . .
C7 C 0.6204(2) 0.750000 0.42525(15) 0.0209(5) Uani 1 2 d S T P . .
C8 C 0.5024(2) 0.750000 0.42311(16) 0.0224(5) Uani 1 2 d S T P . .
C9 C 0.44330(14) 0.68027(10) 0.45415(11) 0.0222(4) Uani 1 1 d . . . . .
C10 C 0.34655(14) 0.70691(10) 0.50309(12) 0.0216(4) Uani 1 1 d . . . . .
C11 C 0.31401(14) 0.66575(10) 0.58127(12) 0.0214(4) Uani 1 1 d . . . . .
C12 C 0.27943(13) 0.70857(10) 0.66259(12) 0.0208(4) Uani 1 1 d . . . . .
C13 C 0.32074(14) 0.66555(10) 0.74642(12) 0.0212(4) Uani 1 1 d . . . . .
C14 C 0.36104(14) 0.70694(10) 0.82679(12) 0.0218(4) Uani 1 1 d . . . . .
C15 C 0.46309(14) 0.68028(10) 0.88059(11) 0.0212(4) Uani 1 1 d . . . . .
C16 C 0.5262(2) 0.750000 0.91296(15) 0.0208(5) Uani 1 2 d S T P . .
C17 C 0.6444(2) 0.750000 0.91326(15) 0.0196(5) Uani 1 2 d S T P . .
C18 C 0.70549(14) 0.68165(10) 0.88392(11) 0.0183(4) Uani 1 1 d . . . . .
C19 C 0.81033(14) 0.70478(9) 0.84409(11) 0.0177(4) Uani 1 1 d . . . . .
C20 C 0.85565(14) 0.65136(9) 0.78072(11) 0.0180(4) Uani 1 1 d . . . . .
C21 C 0.77691(13) 0.59622(9) 0.73075(11) 0.0181(4) Uani 1 1 d . . . . .
C22 C 0.77248(14) 0.59997(9) 0.62720(11) 0.0185(4) Uani 1 1 d . . . . .
C23 C 0.67220(14) 0.57447(9) 0.57616(11) 0.0199(4) Uani 1 1 d . . . . .
C24 C 0.62809(14) 0.61473(10) 0.49080(11) 0.0210(4) Uani 1 1 d . . . . .
C25 C 0.50485(14) 0.61412(10) 0.48719(11) 0.0212(4) Uani 1 1 d . . . . .
C26 C 0.47142(14) 0.57164(9) 0.56884(12) 0.0217(4) Uani 1 1 d . . . . .
C27 C 0.37767(14) 0.59626(10) 0.61475(12) 0.0216(4) Uani 1 1 d . . . . .
C28 C 0.38149(14) 0.59588(9) 0.71694(12) 0.0213(4) Uani 1 1 d . . . . .
C29 C 0.48003(14) 0.57055(9) 0.76848(12) 0.0212(4) Uani 1 1 d . . . . .
C30 C 0.52175(14) 0.61345(10) 0.85203(11) 0.0207(4) Uani 1 1 d . . . . .
C31 C 0.64524(14) 0.61393(10) 0.85466(11) 0.0199(4) Uani 1 1 d . . . . .
C32 C 0.67953(14) 0.57223(9) 0.77280(11) 0.0193(4) Uani 1 1 d . . . . .
C33 C 0.57797(14) 0.54561(9) 0.71979(12) 0.0204(4) Uani 1 1 d . . . . .
C34 C 0.57454(14) 0.54635(9) 0.62276(12) 0.0209(4) Uani 1 1 d . . . . .
C35 C 1.02551(14) 0.58594(10) 0.71035(11) 0.0197(4) Uani 1 1 d . . . . .
C36 C 1.06096(14) 0.56937(10) 0.62175(12) 0.0231(4) Uani 1 1 d . . . . .
H36 H 1.042816 0.604015 0.570159 0.028 Uiso 1 1 calc R U . . .
C37 C 1.12368(15) 0.50076(11) 0.61070(13) 0.0276(4) Uani 1 1 d . . . . .
H37 H 1.148277 0.486916 0.550783 0.033 Uiso 1 1 calc R U . . .
C38 C 1.14992(16) 0.45285(11) 0.68776(13) 0.0310(4) Uani 1 1 d . . . . .
H38 H 1.193535 0.405901 0.681531 0.037 Uiso 1 1 calc R U . . .
C39 C 1.11218(16) 0.47369(11) 0.77450(13) 0.0299(4) Uani 1 1 d . . . . .
C40 C 1.1419(2) 0.42730(14) 0.86481(15) 0.0544(6) Uani 1 1 d . U . . .
C41 C 1.2018(3) 0.48371(16) 0.93616(17) 0.0671(7) Uani 1 1 d . U . A 1
H41 H 1.272703 0.502668 0.912007 0.101 Uiso 1 1 calc R U . A 1
H41A H 1.218942 0.455601 0.995764 0.101 Uiso 1 1 calc R U . A 1
H41B H 1.152098 0.529116 0.946555 0.101 Uiso 1 1 calc R U . A 1
C42 C 1.2229(3) 0.35852(18) 0.8483(2) 0.0919(9) Uani 1 1 d . U . B 1
H42 H 1.183995 0.319378 0.806384 0.138 Uiso 1 1 calc R U . B 1
H42A H 1.246404 0.333300 0.908631 0.138 Uiso 1 1 calc R U . B 1
H42B H 1.290042 0.378790 0.819375 0.138 Uiso 1 1 calc R U . B 1
C43 C 1.0334(3) 0.39725(18) 0.90266(19) 0.0759(8) Uani 1 1 d . U . C 1
H43 H 0.980368 0.441637 0.907919 0.114 Uiso 1 1 calc R U . C 1
H43A H 1.050698 0.373516 0.964894 0.114 Uiso 1 1 calc R U . C 1
H43B H 0.998730 0.357115 0.859743 0.114 Uiso 1 1 calc R U . C 1
C44 C 0.9425(5) 0.2716(2) 0.6176(4) 0.026(2) Uani 0.5 1 d . . P D -1
H44 H 0.992319 0.306253 0.587690 0.032 Uiso 0.5 1 calc R U P D -1
C45 C 0.9589(5) 0.1905(3) 0.6136(4) 0.0293(15) Uani 0.5 1 d . . P D -1
H45 H 1.020548 0.170024 0.581601 0.035 Uiso 0.5 1 calc R U P D -1
C46 C 0.8871(4) 0.1390(3) 0.6552(3) 0.0330(9) Uani 0.5 1 d . . P D -1
H46 H 0.898489 0.083259 0.651030 0.040 Uiso 0.5 1 calc R U P D -1
C47 C 0.7991(4) 0.1683(3) 0.7027(3) 0.0313(9) Uani 0.5 1 d . . P D -1
H47 H 0.749786 0.133033 0.732283 0.038 Uiso 0.5 1 calc R U P D -1
C48 C 0.7824(3) 0.2500(13) 0.70745(17) 0.0288(9) Uani 0.5 1 d . . P D -1
H48 H 0.721096 0.269869 0.740325 0.035 Uiso 0.5 1 calc R U P D -1
C49 C 0.8532(3) 0.3032(2) 0.6653(3) 0.0260(8) Uani 0.5 1 d . . P D -1
C50 C 0.8325(4) 0.3918(3) 0.6677(3) 0.0368(10) Uani 0.5 1 d . . P D -1
H50 H 0.759678 0.404042 0.633143 0.055 Uiso 0.5 1 calc R U P D -1
H50A H 0.894013 0.419443 0.638396 0.055 Uiso 0.5 1 calc R U P D -1
H50B H 0.830418 0.409245 0.733200 0.055 Uiso 0.5 1 calc R U P D -1
C51 C 0.7030(6) 0.2710(3) 0.9379(4) 0.041(2) Uani 0.5 1 d . . P E -1
H51 H 0.751877 0.310780 0.965707 0.050 Uiso 0.5 1 calc R U P E -1
C52 C 0.7341(7) 0.1919(5) 0.9446(4) 0.0544(19) Uani 0.5 1 d . . P E -1
H52 H 0.804752 0.177857 0.976747 0.065 Uiso 0.5 1 calc R U P E -1
C53 C 0.6660(6) 0.1344(3) 0.9064(3) 0.0603(16) Uani 0.5 1 d . . P E -1
H53 H 0.688371 0.080202 0.911267 0.072 Uiso 0.5 1 calc R U P E -1
C54 C 0.5656(9) 0.1547(5) 0.8612(7) 0.055(2) Uani 0.5 1 d . . P E -1
H54 H 0.517359 0.113867 0.834930 0.066 Uiso 0.5 1 calc R U P E -1
C55 C 0.5310(4) 0.2322(3) 0.8519(3) 0.039(2) Uani 0.5 1 d . . P E -1
H55 H 0.460025 0.244604 0.819165 0.047 Uiso 0.5 1 calc R U P E -1
C56 C 0.5999(4) 0.2927(3) 0.8904(3) 0.0363(10) Uani 0.5 1 d . . P E -1
C57 C 0.5625(12) 0.3782(5) 0.8811(7) 0.067(3) Uani 0.5 1 d . . P E -1
H57 H 0.527034 0.387407 0.817666 0.100 Uiso 0.5 1 calc R U P E -1
H57A H 0.628723 0.413120 0.892049 0.100 Uiso 0.5 1 calc R U P E -1
H57B H 0.507382 0.389736 0.927634 0.100 Uiso 0.5 1 calc R U P E -1
N1 N 1.04946(12) 0.53937(8) 0.78490(10) 0.0250(3) Uani 1 1 d . . . . .
O1 O 0.5731(3) 0.750000 0.6683(2) 0.0347(12) Uani 0.645(8) 2 d DS T P . .
H59 H 0.597(11) 0.750000 0.607(3) 0.50(18) Uiso 0.645(8) 2 d DS . P . .
H58 H 0.639(6) 0.750000 0.708(7) 0.19(5) Uiso 0.645(8) 2 d DS . P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C1 1.312(3) 4_575 ?
C1 C2 1.506(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.508(2) . ?
C2 C20 1.523(2) . ?
C2 C35 1.535(2) . ?
C3 C3 1.373(3) 4_575 ?
C3 C4 1.445(2) . ?
C4 C5 1.393(2) . ?
C4 C22 1.467(2) . ?
C5 C6 1.442(2) . ?
C5 C5 1.449(3) 4_575 ?
C6 C24 1.383(2) . ?
C6 C7 1.446(2) . ?
C7 C8 1.389(3) . ?
C8 C9 1.450(2) . ?
C8 C9 1.450(2) 4_575 ?
C9 C25 1.392(2) . ?
C9 C10 1.450(2) . ?
C10 C11 1.389(2) . ?
C10 C10 1.450(3) 4_575 ?
C11 C12 1.447(2) . ?
C11 C27 1.451(2) . ?
C12 C12 1.394(3) 4_575 ?
C12 C13 1.450(2) . ?
C13 C14 1.393(2) . ?
C13 C28 1.451(2) . ?
C14 C14 1.449(3) 4_575 ?
C14 C15 1.449(2) . ?
C15 C30 1.396(2) . ?
C15 C16 1.447(2) . ?
C16 C17 1.391(3) . ?
C17 C18 1.435(2) . ?
C17 C18 1.435(2) 4_575 ?
C18 C31 1.390(2) . ?
C18 C19 1.450(2) . ?
C19 C20 1.406(2) . ?
C19 C19 1.521(3) 4_575 ?
C20 C21 1.460(2) . ?
C21 C32 1.392(2) . ?
C21 C22 1.473(2) . ?
C22 C23 1.409(2) . ?
C23 C34 1.449(2) . ?
C23 C24 1.454(2) . ?
C24 C25 1.449(2) . ?
C25 C26 1.444(2) . ?
C26 C27 1.387(2) . ?
C26 C34 1.453(2) . ?
C27 C28 1.453(2) . ?
C28 C29 1.395(2) . ?
C29 C30 1.447(2) . ?
C29 C33 1.451(2) . ?
C30 C31 1.453(2) . ?
C31 C32 1.443(2) . ?
C32 C33 1.439(2) . ?
C33 C34 1.380(2) . ?
C35 N1 1.333(2) . ?
C35 C36 1.386(2) . ?
C36 C37 1.386(2) . ?
C36 H36 0.9500 . ?
C37 C38 1.379(3) . ?
C37 H37 0.9500 . ?
C38 C39 1.388(3) . ?
C38 H38 0.9500 . ?
C39 N1 1.343(2) . ?
C39 C40 1.523(3) . ?
C40 C43 1.511(4) . ?
C40 C41 1.525(3) . ?
C40 C42 1.528(3) . ?
C41 H41 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C42 H42 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C43 H43 0.9800 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C44 C45 1.379(8) . ?
C44 C49 1.398(8) . ?
C44 H44 0.9500 . ?
C45 C46 1.375(9) . ?
C45 H45 0.9500 . ?
C46 C47 1.371(6) . ?
C46 H46 0.9500 . ?
C47 C48 1.39(2) . ?
C47 H47 0.9500 . ?
C48 C49 1.390(16) . ?
C48 H48 0.9500 . ?
C49 C50 1.511(6) . ?
C50 H50 0.9800 . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C51 C52 1.383(9) . ?
C51 C56 1.395(8) . ?
C51 H51 0.9500 . ?
C52 C53 1.346(11) . ?
C52 H52 0.9500 . ?
C53 C54 1.350(13) . ?
C53 H53 0.9500 . ?
C54 C55 1.371(10) . ?
C54 H54 0.9500 . ?
C55 C56 1.389(7) . ?
C55 H55 0.9500 . ?
C56 C57 1.508(8) . ?
C57 H57 0.9800 . ?
C57 H57A 0.9800 . ?
C57 H57B 0.9800 . ?
O1 H59 0.94(2) . ?
O1 H58 0.93(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 C1 C2 121.69(9) 4_575 . ?
C1 C1 H1 119.2 4_575 . ?
C2 C1 H1 119.2 . . ?
C1 C2 C3 114.51(14) . . ?
C1 C2 C20 109.90(13) . . ?
C3 C2 C20 97.33(12) . . ?
C1 C2 C35 107.58(13) . . ?
C3 C2 C35 114.20(13) . . ?
C20 C2 C35 113.15(13) . . ?
C3 C3 C4 120.16(9) 4_575 . ?
C3 C3 C2 120.28(9) 4_575 . ?
C4 C3 C2 115.43(14) . . ?
C5 C4 C3 116.54(14) . . ?
C5 C4 C22 119.23(14) . . ?
C3 C4 C22 119.12(14) . . ?
C4 C5 C6 122.24(15) . . ?
C4 C5 C5 119.61(9) . 4_575 ?
C6 C5 C5 107.75(9) . 4_575 ?
C24 C6 C5 118.85(15) . . ?
C24 C6 C7 120.72(16) . . ?
C5 C6 C7 108.61(15) . . ?
C8 C7 C6 119.92(12) . 4_575 ?
C8 C7 C6 119.92(12) . . ?
C6 C7 C6 107.23(19) 4_575 . ?
C7 C8 C9 119.73(12) . . ?
C7 C8 C9 119.73(12) . 4_575 ?
C9 C8 C9 108.0(2) . 4_575 ?
C25 C9 C8 120.00(16) . . ?
C25 C9 C10 119.57(15) . . ?
C8 C9 C10 107.97(15) . . ?
C11 C10 C10 119.91(10) . 4_575 ?
C11 C10 C9 120.25(15) . . ?
C10 C10 C9 108.01(10) 4_575 . ?
C10 C11 C12 120.24(15) . . ?
C10 C11 C27 119.94(15) . . ?
C12 C11 C27 107.87(14) . . ?
C12 C12 C11 119.84(10) 4_575 . ?
C12 C12 C13 119.95(9) 4_575 . ?
C11 C12 C13 108.27(14) . . ?
C14 C13 C12 120.07(15) . . ?
C14 C13 C28 119.70(15) . . ?
C12 C13 C28 107.94(14) . . ?
C13 C14 C14 119.98(10) . 4_575 ?
C13 C14 C15 119.99(15) . . ?
C14 C14 C15 108.03(10) 4_575 . ?
C30 C15 C16 119.47(16) . . ?
C30 C15 C14 120.31(15) . . ?
C16 C15 C14 107.79(15) . . ?
C17 C16 C15 119.49(12) . . ?
C17 C16 C15 119.49(12) . 4_575 ?
C15 C16 C15 108.4(2) . 4_575 ?
C16 C17 C18 121.48(12) . . ?
C16 C17 C18 121.48(12) . 4_575 ?
C18 C17 C18 106.5(2) . 4_575 ?
C31 C18 C17 119.19(16) . . ?
C31 C18 C19 122.26(15) . . ?
C17 C18 C19 111.04(15) . . ?
C20 C19 C18 116.99(14) . . ?
C20 C19 C19 129.73(9) . 4_575 ?
C18 C19 C19 105.57(9) . 4_575 ?
C19 C20 C21 117.48(14) . . ?
C19 C20 C2 124.67(14) . . ?
C21 C20 C2 114.22(13) . . ?
C32 C21 C20 119.27(15) . . ?
C32 C21 C22 118.20(14) . . ?
C20 C21 C22 115.84(14) . . ?
C23 C22 C4 117.58(14) . . ?
C23 C22 C21 118.11(15) . . ?
C4 C22 C21 115.41(13) . . ?
C22 C23 C34 121.83(15) . . ?
C22 C23 C24 121.68(15) . . ?
C34 C23 C24 106.70(14) . . ?
C6 C24 C25 119.42(15) . . ?
C6 C24 C23 119.91(14) . . ?
C25 C24 C23 108.83(15) . . ?
C9 C25 C26 120.14(16) . . ?
C9 C25 C24 120.18(15) . . ?
C26 C25 C24 107.82(14) . . ?
C27 C26 C25 120.32(15) . . ?
C27 C26 C34 120.16(15) . . ?
C25 C26 C34 107.70(15) . . ?
C26 C27 C11 119.76(15) . . ?
C26 C27 C28 120.20(15) . . ?
C11 C27 C28 108.09(14) . . ?
C29 C28 C13 120.25(15) . . ?
C29 C28 C27 119.52(15) . . ?
C13 C28 C27 107.83(14) . . ?
C28 C29 C30 120.04(15) . . ?
C28 C29 C33 119.83(15) . . ?
C30 C29 C33 107.63(14) . . ?
C15 C30 C29 119.71(15) . . ?
C15 C30 C31 120.28(15) . . ?
C29 C30 C31 107.69(14) . . ?
C18 C31 C32 118.27(15) . . ?
C18 C31 C30 120.06(15) . . ?
C32 C31 C30 108.36(14) . . ?
C21 C32 C33 122.99(15) . . ?
C21 C32 C31 119.63(15) . . ?
C33 C32 C31 107.71(14) . . ?
C34 C33 C32 119.04(15) . . ?
C34 C33 C29 120.64(15) . . ?
C32 C33 C29 108.61(14) . . ?
C33 C34 C23 119.69(15) . . ?
C33 C34 C26 119.64(15) . . ?
C23 C34 C26 108.89(14) . . ?
N1 C35 C36 123.13(15) . . ?
N1 C35 C2 113.65(14) . . ?
C36 C35 C2 122.90(15) . . ?
C37 C36 C35 117.99(16) . . ?
C37 C36 H36 121.0 . . ?
C35 C36 H36 121.0 . . ?
C38 C37 C36 119.16(17) . . ?
C38 C37 H37 120.4 . . ?
C36 C37 H37 120.4 . . ?
C37 C38 C39 119.54(17) . . ?
C37 C38 H38 120.2 . . ?
C39 C38 H38 120.2 . . ?
N1 C39 C38 121.35(17) . . ?
N1 C39 C40 115.02(17) . . ?
C38 C39 C40 123.58(17) . . ?
C43 C40 C39 108.9(2) . . ?
C43 C40 C41 109.4(2) . . ?
C39 C40 C41 108.11(19) . . ?
C43 C40 C42 110.8(3) . . ?
C39 C40 C42 111.5(2) . . ?
C41 C40 C42 108.1(2) . . ?
C40 C41 H41 109.5 . . ?
C40 C41 H41A 109.5 . . ?
H41 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
H41 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C40 C42 H42 109.5 . . ?
C40 C42 H42A 109.5 . . ?
H42 C42 H42A 109.5 . . ?
C40 C42 H42B 109.5 . . ?
H42 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C40 C43 H43 109.5 . . ?
C40 C43 H43A 109.5 . . ?
H43 C43 H43A 109.5 . . ?
C40 C43 H43B 109.5 . . ?
H43 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C45 C44 C49 120.6(6) . . ?
C45 C44 H44 119.7 . . ?
C49 C44 H44 119.7 . . ?
C46 C45 C44 120.9(6) . . ?
C46 C45 H45 119.6 . . ?
C44 C45 H45 119.6 . . ?
C47 C46 C45 119.8(5) . . ?
C47 C46 H46 120.1 . . ?
C45 C46 H46 120.1 . . ?
C46 C47 C48 119.6(5) . . ?
C46 C47 H47 120.2 . . ?
C48 C47 H47 120.2 . . ?
C47 C48 C49 121.6(6) . . ?
C47 C48 H48 119.2 . . ?
C49 C48 H48 119.2 . . ?
C48 C49 C44 117.5(8) . . ?
C48 C49 C50 121.5(8) . . ?
C44 C49 C50 121.0(4) . . ?
C49 C50 H50 109.5 . . ?
C49 C50 H50A 109.5 . . ?
H50 C50 H50A 109.5 . . ?
C49 C50 H50B 109.5 . . ?
H50 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C52 C51 C56 120.1(7) . . ?
C52 C51 H51 119.9 . . ?
C56 C51 H51 119.9 . . ?
C53 C52 C51 121.1(7) . . ?
C53 C52 H52 119.4 . . ?
C51 C52 H52 119.4 . . ?
C52 C53 C54 119.2(6) . . ?
C52 C53 H53 120.4 . . ?
C54 C53 H53 120.4 . . ?
C53 C54 C55 122.1(8) . . ?
C53 C54 H54 119.0 . . ?
C55 C54 H54 119.0 . . ?
C54 C55 C56 119.8(6) . . ?
C54 C55 H55 120.1 . . ?
C56 C55 H55 120.1 . . ?
C55 C56 C51 117.6(5) . . ?
C55 C56 C57 120.3(6) . . ?
C51 C56 C57 122.0(7) . . ?
C56 C57 H57 109.5 . . ?
C56 C57 H57A 109.5 . . ?
H57 C57 H57A 109.5 . . ?
C56 C57 H57B 109.5 . . ?
H57 C57 H57B 109.5 . . ?
H57A C57 H57B 109.5 . . ?
C35 N1 C39 118.81(15) . . ?
H59 O1 H58 106(3) . . ?

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
C1 C1 C2 C3 21.13(16) 4_575 . . . ?
C1 C1 C2 C20 -87.18(12) 4_575 . . . ?
C1 C1 C2 C35 149.23(9) 4_575 . . . ?
C1 C2 C3 C3 -20.81(16) . . . 4_575 ?
C20 C2 C3 C3 95.03(10) . . . 4_575 ?
C35 C2 C3 C3 -145.47(10) . . . 4_575 ?
C1 C2 C3 C4 -177.99(13) . . . . ?
C20 C2 C3 C4 -62.15(16) . . . . ?
C35 C2 C3 C4 57.35(19) . . . . ?
C3 C3 C4 C5 21.74(16) 4_575 . . . ?
C2 C3 C4 C5 178.95(14) . . . . ?
C3 C3 C4 C22 -132.81(11) 4_575 . . . ?
C2 C3 C4 C22 24.4(2) . . . . ?
C3 C4 C5 C6 -162.25(15) . . . . ?
C22 C4 C5 C6 -7.7(2) . . . . ?
C3 C4 C5 C5 -21.62(16) . . . 4_575 ?
C22 C4 C5 C5 132.90(11) . . . 4_575 ?
C4 C5 C6 C24 2.7(2) . . . . ?
C5 C5 C6 C24 -141.93(12) 4_575 . . . ?
C4 C5 C6 C7 145.92(17) . . . . ?
C5 C5 C6 C7 1.30(15) 4_575 . . . ?
C24 C6 C7 C8 -1.0(3) . . . . ?
C5 C6 C7 C8 -143.43(18) . . . . ?
C24 C6 C7 C6 140.34(14) . . . 4_575 ?
C5 C6 C7 C6 -2.1(2) . . . 4_575 ?
C6 C7 C8 C9 -136.98(17) 4_575 . . . ?
C6 C7 C8 C9 -0.5(3) . . . . ?
C6 C7 C8 C9 0.5(3) 4_575 . . 4_575 ?
C6 C7 C8 C9 136.97(17) . . . 4_575 ?
C7 C8 C9 C25 0.9(3) . . . . ?
C9 C8 C9 C25 -140.94(14) 4_575 . . . ?
C7 C8 C9 C10 142.76(18) . . . . ?
C9 C8 C9 C10 0.9(2) 4_575 . . . ?
C25 C9 C10 C11 -1.3(2) . . . . ?
C8 C9 C10 C11 -143.37(16) . . . . ?
C25 C9 C10 C10 141.48(12) . . . 4_575 ?
C8 C9 C10 C10 -0.55(14) . . . 4_575 ?
C10 C10 C11 C12 0.36(19) 4_575 . . . ?
C9 C10 C11 C12 138.82(16) . . . . ?
C10 C10 C11 C27 -137.86(12) 4_575 . . . ?
C9 C10 C11 C27 0.6(2) . . . . ?
C10 C11 C12 C12 -0.36(19) . . . 4_575 ?
C27 C11 C12 C12 142.29(9) . . . 4_575 ?
C10 C11 C12 C13 -143.06(15) . . . . ?
C27 C11 C12 C13 -0.41(18) . . . . ?
C12 C12 C13 C14 -0.36(18) 4_575 . . . ?
C11 C12 C13 C14 142.29(15) . . . . ?
C12 C12 C13 C28 -142.49(9) 4_575 . . . ?
C11 C12 C13 C28 0.16(18) . . . . ?
C12 C13 C14 C14 0.36(18) . . . 4_575 ?
C28 C13 C14 C14 138.11(12) . . . 4_575 ?
C12 C13 C14 C15 -137.83(16) . . . . ?
C28 C13 C14 C15 -0.1(2) . . . . ?
C13 C14 C15 C30 0.3(2) . . . . ?
C14 C14 C15 C30 -142.27(13) 4_575 . . . ?
C13 C14 C15 C16 142.13(17) . . . . ?
C14 C14 C15 C16 -0.48(15) 4_575 . . . ?
C30 C15 C16 C17 1.3(3) . . . . ?
C14 C15 C16 C17 -140.83(18) . . . . ?
C30 C15 C16 C15 142.95(13) . . . 4_575 ?
C14 C15 C16 C15 0.8(2) . . . 4_575 ?
C15 C16 C17 C18 -1.3(3) . . . . ?
C15 C16 C17 C18 -138.66(17) 4_575 . . . ?
C15 C16 C17 C18 138.66(17) . . . 4_575 ?
C15 C16 C17 C18 1.3(3) 4_575 . . 4_575 ?
C16 C17 C18 C31 -0.1(3) . . . . ?
C18 C17 C18 C31 -145.16(13) 4_575 . . . ?
C16 C17 C18 C19 150.38(18) . . . . ?
C18 C17 C18 C19 5.3(2) 4_575 . . . ?
C31 C18 C19 C20 -6.3(2) . . . . ?
C17 C18 C19 C20 -155.72(15) . . . . ?
C31 C18 C19 C19 146.11(12) . . . 4_575 ?
C17 C18 C19 C19 -3.28(14) . . . 4_575 ?
C18 C19 C20 C21 24.7(2) . . . . ?
C19 C19 C20 C21 -119.92(12) 4_575 . . . ?
C18 C19 C20 C2 -178.11(14) . . . . ?
C19 C19 C20 C2 37.31(19) 4_575 . . . ?
C1 C2 C20 C19 31.0(2) . . . . ?
C3 C2 C20 C19 -88.40(17) . . . . ?
C35 C2 C20 C19 151.30(15) . . . . ?
C1 C2 C20 C21 -171.07(13) . . . . ?
C3 C2 C20 C21 69.49(15) . . . . ?
C35 C2 C20 C21 -50.81(17) . . . . ?
C19 C20 C21 C32 -28.6(2) . . . . ?
C2 C20 C21 C32 171.85(13) . . . . ?
C19 C20 C21 C22 122.28(16) . . . . ?
C2 C20 C21 C22 -37.30(19) . . . . ?
C5 C4 C22 C23 8.0(2) . . . . ?
C3 C4 C22 C23 161.85(14) . . . . ?
C5 C4 C22 C21 -138.79(15) . . . . ?
C3 C4 C22 C21 15.1(2) . . . . ?
C32 C21 C22 C23 -3.8(2) . . . . ?
C20 C21 C22 C23 -154.96(14) . . . . ?
C32 C21 C22 C4 142.82(15) . . . . ?
C20 C21 C22 C4 -8.4(2) . . . . ?
C4 C22 C23 C34 -144.90(15) . . . . ?
C21 C22 C23 C34 1.0(2) . . . . ?
C4 C22 C23 C24 -3.6(2) . . . . ?
C21 C22 C23 C24 142.29(15) . . . . ?
C5 C6 C24 C25 140.72(16) . . . . ?
C7 C6 C24 C25 2.0(2) . . . . ?
C5 C6 C24 C23 2.0(2) . . . . ?
C7 C6 C24 C23 -136.75(17) . . . . ?
C22 C23 C24 C6 -1.4(2) . . . . ?
C34 C23 C24 C6 144.96(15) . . . . ?
C22 C23 C24 C25 -144.02(16) . . . . ?
C34 C23 C24 C25 2.31(17) . . . . ?
C8 C9 C25 C26 138.43(17) . . . . ?
C10 C9 C25 C26 0.9(2) . . . . ?
C8 C9 C25 C24 0.1(2) . . . . ?
C10 C9 C25 C24 -137.40(16) . . . . ?
C6 C24 C25 C9 -1.6(2) . . . . ?
C23 C24 C25 C9 141.31(15) . . . . ?
C6 C24 C25 C26 -144.41(15) . . . . ?
C23 C24 C25 C26 -1.54(17) . . . . ?
C9 C25 C26 C27 0.2(2) . . . . ?
C24 C25 C26 C27 143.05(15) . . . . ?
C9 C25 C26 C34 -142.71(15) . . . . ?
C24 C25 C26 C34 0.16(17) . . . . ?
C25 C26 C27 C11 -0.9(2) . . . . ?
C34 C26 C27 C11 137.43(16) . . . . ?
C25 C26 C27 C28 -139.20(16) . . . . ?
C34 C26 C27 C28 -0.9(2) . . . . ?
C10 C11 C27 C26 0.5(2) . . . . ?
C12 C11 C27 C26 -142.27(15) . . . . ?
C10 C11 C27 C28 143.28(15) . . . . ?
C12 C11 C27 C28 0.50(18) . . . . ?
C14 C13 C28 C29 -0.3(2) . . . . ?
C12 C13 C28 C29 142.02(15) . . . . ?
C14 C13 C28 C27 -142.15(15) . . . . ?
C12 C13 C28 C27 0.14(17) . . . . ?
C26 C27 C28 C29 0.0(2) . . . . ?
C11 C27 C28 C29 -142.60(15) . . . . ?
C26 C27 C28 C13 142.18(15) . . . . ?
C11 C27 C28 C13 -0.40(17) . . . . ?
C13 C28 C29 C30 0.4(2) . . . . ?
C27 C28 C29 C30 137.90(16) . . . . ?
C13 C28 C29 C33 -136.92(16) . . . . ?
C27 C28 C29 C33 0.6(2) . . . . ?
C16 C15 C30 C29 -137.67(17) . . . . ?
C14 C15 C30 C29 -0.2(2) . . . . ?
C16 C15 C30 C31 -0.1(2) . . . . ?
C14 C15 C30 C31 137.36(16) . . . . ?
C28 C29 C30 C15 -0.1(2) . . . . ?
C33 C29 C30 C15 141.76(15) . . . . ?
C28 C29 C30 C31 -142.45(15) . . . . ?
C33 C29 C30 C31 -0.56(17) . . . . ?
C17 C18 C31 C32 137.79(16) . . . . ?
C19 C18 C31 C32 -9.2(2) . . . . ?
C17 C18 C31 C30 1.4(2) . . . . ?
C19 C18 C31 C30 -145.67(15) . . . . ?
C15 C30 C31 C18 -1.3(2) . . . . ?
C29 C30 C31 C18 140.77(15) . . . . ?
C15 C30 C31 C32 -141.53(15) . . . . ?
C29 C30 C31 C32 0.53(17) . . . . ?
C20 C21 C32 C33 154.77(15) . . . . ?
C22 C21 C32 C33 4.6(2) . . . . ?
C20 C21 C32 C31 12.9(2) . . . . ?
C22 C21 C32 C31 -137.26(15) . . . . ?
C18 C31 C32 C21 5.7(2) . . . . ?
C30 C31 C32 C21 146.76(14) . . . . ?
C18 C31 C32 C33 -141.35(15) . . . . ?
C30 C31 C32 C33 -0.30(17) . . . . ?
C21 C32 C33 C34 -2.4(2) . . . . ?
C31 C32 C33 C34 143.27(15) . . . . ?
C21 C32 C33 C29 -145.75(15) . . . . ?
C31 C32 C33 C29 -0.05(17) . . . . ?
C28 C29 C33 C34 -0.3(2) . . . . ?
C30 C29 C33 C34 -142.25(15) . . . . ?
C28 C29 C33 C32 142.37(15) . . . . ?
C30 C29 C33 C32 0.38(17) . . . . ?
C32 C33 C34 C23 -0.6(2) . . . . ?
C29 C33 C34 C23 138.27(16) . . . . ?
C32 C33 C34 C26 -139.47(16) . . . . ?
C29 C33 C34 C26 -0.6(2) . . . . ?
C22 C23 C34 C33 1.2(2) . . . . ?
C24 C23 C34 C33 -145.04(15) . . . . ?
C22 C23 C34 C26 144.06(15) . . . . ?
C24 C23 C34 C26 -2.21(17) . . . . ?
C27 C26 C34 C33 1.2(2) . . . . ?
C25 C26 C34 C33 144.15(15) . . . . ?
C27 C26 C34 C23 -141.68(15) . . . . ?
C25 C26 C34 C23 1.29(17) . . . . ?
C1 C2 C35 N1 63.79(17) . . . . ?
C3 C2 C35 N1 -167.93(14) . . . . ?
C20 C2 C35 N1 -57.80(18) . . . . ?
C1 C2 C35 C36 -109.89(17) . . . . ?
C3 C2 C35 C36 18.4(2) . . . . ?
C20 C2 C35 C36 128.53(16) . . . . ?
N1 C35 C36 C37 0.4(2) . . . . ?
C2 C35 C36 C37 173.47(15) . . . . ?
C35 C36 C37 C38 -1.2(2) . . . . ?
C36 C37 C38 C39 0.7(3) . . . . ?
C37 C38 C39 N1 0.6(3) . . . . ?
C37 C38 C39 C40 -176.6(2) . . . . ?
N1 C39 C40 C43 63.1(3) . . . . ?
C38 C39 C40 C43 -119.5(2) . . . . ?
N1 C39 C40 C41 -55.7(3) . . . . ?
C38 C39 C40 C41 121.7(2) . . . . ?
N1 C39 C40 C42 -174.3(2) . . . . ?
C38 C39 C40 C42 3.0(3) . . . . ?
C49 C44 C45 C46 0.8(10) . . . . ?
C44 C45 C46 C47 -1.1(9) . . . . ?
C45 C46 C47 C48 0.8(6) . . . . ?
C46 C47 C48 C49 -0.2(5) . . . . ?
C47 C48 C49 C44 0.0(5) . . . . ?
C47 C48 C49 C50 177.9(3) . . . . ?
C45 C44 C49 C48 -0.3(8) . . . . ?
C45 C44 C49 C50 -178.2(6) . . . . ?
C56 C51 C52 C53 -0.5(11) . . . . ?
C51 C52 C53 C54 -0.2(10) . . . . ?
C52 C53 C54 C55 0.7(10) . . . . ?
C53 C54 C55 C56 -0.5(10) . . . . ?
C54 C55 C56 C51 -0.2(7) . . . . ?
C54 C55 C56 C57 -179.6(4) . . . . ?
C52 C51 C56 C55 0.7(9) . . . . ?
C52 C51 C56 C57 -179.9(7) . . . . ?
C36 C35 N1 C39 0.9(2) . . . . ?
C2 C35 N1 C39 -172.76(15) . . . . ?
C38 C39 N1 C35 -1.4(3) . . . . ?
C40 C39 N1 C35 176.02(18) . . . . ?

_refine_diff_density_max         0.502
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.050

# start Validation Reply Form
_vrf_PLAT420_2w8_a               
;
PROBLEM: D-H Bond Without Acceptor  O1       --H58      .     Please Check 
         D-H Bond Without Acceptor  O1       --H59      .     Please Check 
RESPONSE: The encapsulated H2O molecule inside fullerenes behaves 
like a gaseous single water molecule in vacuo 
without definitive interactions with H-bonding acceptors 
as discussed in ChemPhysChem 2017, 18, 1229-1233.
Therefore, the absence of acceptors for both H58 and H59 are reasonable. 
;



####################################################################### 
# 
# 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_1DAadt_a
_database_code_depnum_ccdc_archive 'CCDC 2190897'
loop_
_audit_author_name
_audit_author_address
'Yoshifumi Hashikawa'
;ICR, Kyoto Univ
Japan
;
_audit_update_record             
;
2022-07-18 deposited with the CCDC.	2023-01-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H31 N3 O2'
_chemical_formula_weight         489.60

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                   23.689(3)
_cell_length_b                   19.477(3)
_cell_length_c                   11.8763(15)
_cell_angle_alpha                90
_cell_angle_beta                 98.836(2)
_cell_angle_gamma                90
_cell_volume                     5414.5(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6164
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      24.99

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_F_000             2080
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6009
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Smart APEX II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26065
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.026
_diffrn_reflns_theta_max         25.061
_diffrn_reflns_theta_full        25.061
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             9562
_reflns_number_gt                6841
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9562
_refine_ls_number_parameters     679
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1592
_refine_ls_wR_factor_gt          0.1396
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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 0.49981(8) 0.59933(9) 0.74751(14) 0.0276(4) Uani 1 1 d . . . . .
O1 O 0.45734(7) 0.64307(8) 0.57425(12) 0.0360(4) Uani 1 1 d . . . . .
N2 N 0.57232(8) 0.63307(9) 0.31589(14) 0.0274(4) Uani 1 1 d . . . . .
O2 O 0.56329(6) 0.54764(8) 0.88994(12) 0.0317(4) Uani 1 1 d . . . . .
N3 N 0.69789(8) 0.43463(9) 0.77214(15) 0.0282(4) Uani 1 1 d . . . . .
O3 O 0.90204(7) 0.54169(8) 0.61718(11) 0.0311(4) Uani 1 1 d . . . . .
N4 N 0.84618(7) 0.59617(8) 0.73245(13) 0.0229(4) Uani 1 1 d . . . . .
O4 O 0.80584(6) 0.63177(7) 0.88746(12) 0.0279(4) Uani 1 1 d . . . . .
C1 C 0.44218(10) 0.68667(13) 0.82130(19) 0.0382(6) Uani 1 1 d . . . . .
H1 H 0.460188 0.720672 0.781782 0.046 Uiso 1 1 calc R U . . .
C2 C 0.40043(11) 0.70511(16) 0.8863(2) 0.0478(7) Uani 1 1 d . . . . .
H2 H 0.389948 0.751904 0.892113 0.057 Uiso 1 1 calc R U . . .
C3 C 0.37432(11) 0.65472(18) 0.9422(2) 0.0521(8) Uani 1 1 d . . . . .
H3 H 0.344992 0.666913 0.984820 0.063 Uiso 1 1 calc R U . . .
C4 C 0.39049(11) 0.58706(16) 0.9367(2) 0.0466(7) Uani 1 1 d . . . . .
H4 H 0.372813 0.553091 0.976947 0.056 Uiso 1 1 calc R U . . .
N5 N 0.97424(7) 0.35840(9) 0.75676(14) 0.0240(4) Uani 1 1 d . . . . .
C5 C 0.43207(10) 0.56816(14) 0.87344(19) 0.0379(6) Uani 1 1 d . . . . .
H5 H 0.443360 0.521495 0.869997 0.045 Uiso 1 1 calc R U . . .
N6 N 0.84770(7) 0.49514(9) 1.18137(13) 0.0242(4) Uani 1 1 d . . . . .
C6 C 0.45715(9) 0.61840(12) 0.81489(17) 0.0296(5) Uani 1 1 d . . . . .
C7 C 0.55048(9) 0.56448(11) 0.79127(17) 0.0255(5) Uani 1 1 d . . . . .
C8 C 0.58128(9) 0.55367(10) 0.69247(16) 0.0242(5) Uani 1 1 d . . . . .
C9 C 0.63296(9) 0.52006(10) 0.68813(17) 0.0251(5) Uani 1 1 d . . . . .
C10 C 0.64768(10) 0.51128(12) 0.57920(18) 0.0301(5) Uani 1 1 d . . . . .
H6 H 0.681210 0.486102 0.571393 0.036 Uiso 1 1 calc R U . . .
C11 C 0.61519(10) 0.53793(12) 0.48316(18) 0.0310(5) Uani 1 1 d . . . . .
H7 H 0.627483 0.531398 0.411456 0.037 Uiso 1 1 calc R U . . .
C12 C 0.56442(9) 0.57448(11) 0.48756(17) 0.0256(5) Uani 1 1 d . . . . .
C13 C 0.54767(9) 0.57968(10) 0.59468(17) 0.0246(5) Uani 1 1 d . . . . .
C14 C 0.53530(10) 0.60515(11) 0.37846(17) 0.0262(5) Uani 1 1 d . . . . .
C15 C 0.47698(10) 0.60218(11) 0.34140(18) 0.0298(5) Uani 1 1 d . . . . .
H8 H 0.451719 0.583947 0.388668 0.036 Uiso 1 1 calc R U . . .
C16 C 0.45674(10) 0.62654(12) 0.23369(18) 0.0327(5) Uani 1 1 d . . . . .
H9 H 0.417186 0.623602 0.204345 0.039 Uiso 1 1 calc R U . . .
C17 C 0.49425(10) 0.65524(12) 0.16868(18) 0.0328(6) Uani 1 1 d . . . . .
H10 H 0.480649 0.672138 0.094430 0.039 Uiso 1 1 calc R U . . .
C18 C 0.55199(10) 0.65920(11) 0.21262(17) 0.0276(5) Uani 1 1 d . . . . .
C19 C 0.59718(10) 0.69356(12) 0.15271(17) 0.0323(5) Uani 1 1 d . . . . .
C20 C 0.57206(11) 0.71976(13) 0.03393(18) 0.0387(6) Uani 1 1 d . . . . .
H27 H 0.555832 0.681158 -0.013219 0.058 Uiso 1 1 calc R U . . .
H28 H 0.602261 0.741451 -0.001530 0.058 Uiso 1 1 calc R U . . .
H29 H 0.542002 0.753434 0.040553 0.058 Uiso 1 1 calc R U . . .
C21 C 0.62097(11) 0.75474(13) 0.22741(19) 0.0386(6) Uani 1 1 d . . . . .
H30 H 0.590164 0.787561 0.232978 0.058 Uiso 1 1 calc R U . . .
H31 H 0.651135 0.777331 0.193045 0.058 Uiso 1 1 calc R U . . .
H32 H 0.636748 0.738259 0.303736 0.058 Uiso 1 1 calc R U . . .
C22 C 0.64513(11) 0.64243(14) 0.1427(2) 0.0448(7) Uani 1 1 d . . . . .
H33 H 0.661543 0.626161 0.218818 0.067 Uiso 1 1 calc R U . . .
H34 H 0.674874 0.664998 0.107097 0.067 Uiso 1 1 calc R U . . .
H35 H 0.629698 0.603344 0.095844 0.067 Uiso 1 1 calc R U . . .
C23 C 0.67348(9) 0.49547(11) 0.78766(17) 0.0252(5) Uani 1 1 d . . . . .
C24 C 0.68811(9) 0.53493(11) 0.88537(18) 0.0280(5) Uani 1 1 d . . . . .
H11 H 0.670301 0.577952 0.893649 0.034 Uiso 1 1 calc R U . . .
C25 C 0.72942(9) 0.50953(12) 0.97011(18) 0.0309(5) Uani 1 1 d . . . . .
H12 H 0.740658 0.535156 1.037917 0.037 Uiso 1 1 calc R U . . .
C26 C 0.75422(10) 0.44663(12) 0.95543(18) 0.0308(5) Uani 1 1 d . . . . .
H13 H 0.782394 0.428588 1.013446 0.037 Uiso 1 1 calc R U . . .
C27 C 0.73783(9) 0.40983(11) 0.85554(19) 0.0293(5) Uani 1 1 d . . . . .
C28 C 0.76481(10) 0.34167(12) 0.8295(2) 0.0370(6) Uani 1 1 d . . . . .
C29 C 0.71859(14) 0.29273(15) 0.7760(3) 0.0722(10) Uani 1 1 d . . . . .
H54 H 0.692419 0.283103 0.830398 0.108 Uiso 1 1 calc R U . . .
H55 H 0.736132 0.249787 0.755760 0.108 Uiso 1 1 calc R U . . .
H56 H 0.697347 0.313646 0.707191 0.108 Uiso 1 1 calc R U . . .
C30 C 0.79687(18) 0.30858(18) 0.9356(3) 0.0990(15) Uani 1 1 d . . . . .
H57 H 0.827183 0.339526 0.970703 0.148 Uiso 1 1 calc R U . . .
H58 H 0.813793 0.265269 0.915309 0.148 Uiso 1 1 calc R U . . .
H59 H 0.770403 0.299504 0.989718 0.148 Uiso 1 1 calc R U . . .
C31 C 0.80482(18) 0.3565(2) 0.7446(4) 0.1051(16) Uani 1 1 d . . . . .
H60 H 0.784706 0.383517 0.681276 0.158 Uiso 1 1 calc R U . . .
H61 H 0.817795 0.313130 0.715488 0.158 Uiso 1 1 calc R U . . .
H62 H 0.837880 0.382432 0.782249 0.158 Uiso 1 1 calc R U . . .
C35 C 0.84471(10) 0.68070(11) 0.58215(17) 0.0287(5) Uani 1 1 d . . . . .
H14 H 0.885270 0.681971 0.596716 0.034 Uiso 1 1 calc R U . . .
C36 C 0.81521(10) 0.72049(11) 0.49640(18) 0.0313(5) Uani 1 1 d . . . . .
H15 H 0.835554 0.749482 0.452339 0.038 Uiso 1 1 calc R U . . .
C37 C 0.75671(11) 0.71832(11) 0.47458(18) 0.0336(6) Uani 1 1 d . . . . .
H16 H 0.736593 0.746143 0.416030 0.040 Uiso 1 1 calc R U . . .
C38 C 0.72696(11) 0.67565(12) 0.5378(2) 0.0368(6) Uani 1 1 d . . . . .
H17 H 0.686458 0.673547 0.521651 0.044 Uiso 1 1 calc R U . . .
C39 C 0.75635(10) 0.63567(12) 0.62527(18) 0.0308(5) Uani 1 1 d . . . . .
H18 H 0.736094 0.606569 0.669324 0.037 Uiso 1 1 calc R U . . .
C40 C 0.81485(9) 0.63893(10) 0.64681(16) 0.0231(5) Uani 1 1 d . . . . .
C41 C 0.83982(9) 0.59596(10) 0.84849(17) 0.0219(5) Uani 1 1 d . . . . .
C42 C 0.88150(9) 0.54432(10) 0.90466(16) 0.0214(5) Uani 1 1 d . . . . .
C43 C 0.88994(9) 0.51871(10) 1.01593(16) 0.0221(5) Uani 1 1 d . . . . .
C44 C 0.92688(9) 0.46232(10) 1.03575(17) 0.0246(5) Uani 1 1 d . . . . .
H19 H 0.933542 0.442814 1.109922 0.030 Uiso 1 1 calc R U . . .
C45 C 0.95394(9) 0.43398(11) 0.95194(17) 0.0250(5) Uani 1 1 d . . . . .
H20 H 0.977881 0.395109 0.969665 0.030 Uiso 1 1 calc R U . . .
C46 C 0.94707(9) 0.46106(10) 0.84120(16) 0.0220(5) Uani 1 1 d . . . . .
C47 C 0.91009(9) 0.51614(10) 0.82069(16) 0.0217(5) Uani 1 1 d . . . . .
C48 C 0.97723(9) 0.42714(10) 0.75547(16) 0.0230(5) Uani 1 1 d . . . . .
C49 C 1.00772(9) 0.46288(11) 0.68309(17) 0.0278(5) Uani 1 1 d . . . . .
H21 H 1.009502 0.511604 0.684726 0.033 Uiso 1 1 calc R U . . .
C50 C 1.03520(10) 0.42585(12) 0.60911(17) 0.0308(5) Uani 1 1 d . . . . .
H22 H 1.056373 0.448681 0.558529 0.037 Uiso 1 1 calc R U . . .
C51 C 1.03163(10) 0.35488(12) 0.60926(17) 0.0304(5) Uani 1 1 d . . . . .
H23 H 1.050298 0.328634 0.558478 0.037 Uiso 1 1 calc R U . . .
C52 C 1.00062(9) 0.32216(11) 0.68406(17) 0.0262(5) Uani 1 1 d . . . . .
C53 C 0.99121(10) 0.24466(12) 0.68619(17) 0.0306(5) Uani 1 1 d . . . . .
C54 C 1.03822(10) 0.20577(13) 0.63763(19) 0.0366(6) Uani 1 1 d . . . . .
H36 H 1.036910 0.217785 0.557143 0.055 Uiso 1 1 calc R U . . .
H37 H 1.032288 0.156248 0.644550 0.055 Uiso 1 1 calc R U . . .
H38 H 1.075566 0.218383 0.680125 0.055 Uiso 1 1 calc R U . . .
C55 C 0.93296(10) 0.22975(12) 0.6155(2) 0.0391(6) Uani 1 1 d . . . . .
H39 H 0.903449 0.256193 0.645829 0.059 Uiso 1 1 calc R U . . .
H40 H 0.924505 0.180630 0.619431 0.059 Uiso 1 1 calc R U . . .
H41 H 0.933573 0.242874 0.536081 0.059 Uiso 1 1 calc R U . . .
C56 C 0.99051(12) 0.22096(13) 0.8089(2) 0.0442(7) Uani 1 1 d . . . . .
H42 H 1.025773 0.235742 0.856983 0.066 Uiso 1 1 calc R U . . .
H43 H 0.987753 0.170780 0.810803 0.066 Uiso 1 1 calc R U . . .
H44 H 0.957558 0.241182 0.837403 0.066 Uiso 1 1 calc R U . . .
C57 C 0.86230(9) 0.54459(10) 1.11242(16) 0.0227(5) Uani 1 1 d . . . . .
C58 C 0.85374(9) 0.61373(11) 1.13166(17) 0.0266(5) Uani 1 1 d . . . . .
H24 H 0.865810 0.647770 1.083240 0.032 Uiso 1 1 calc R U . . .
C59 C 0.82734(10) 0.63178(12) 1.22256(18) 0.0321(5) Uani 1 1 d . . . . .
H25 H 0.820512 0.678755 1.237269 0.038 Uiso 1 1 calc R U . . .
C60 C 0.81075(10) 0.58129(12) 1.29259(19) 0.0324(5) Uani 1 1 d . . . . .
H26 H 0.792116 0.593180 1.355209 0.039 Uiso 1 1 calc R U . . .
C61 C 0.82173(9) 0.51269(11) 1.27006(17) 0.0260(5) Uani 1 1 d . . . . .
C62 C 0.80563(11) 0.45261(12) 1.34171(18) 0.0343(6) Uani 1 1 d . . . . .
C63 C 0.86019(13) 0.41323(14) 1.3923(2) 0.0560(8) Uani 1 1 d . . . . .
H45 H 0.881092 0.399586 1.330793 0.084 Uiso 1 1 calc R U . . .
H46 H 0.849674 0.372192 1.432095 0.084 Uiso 1 1 calc R U . . .
H47 H 0.884464 0.442894 1.446146 0.084 Uiso 1 1 calc R U . . .
C64 C 0.76545(17) 0.40487(18) 1.2659(2) 0.0781(12) Uani 1 1 d . . . . .
H48 H 0.731567 0.430512 1.231441 0.117 Uiso 1 1 calc R U . . .
H49 H 0.753842 0.367079 1.311806 0.117 Uiso 1 1 calc R U . . .
H50 H 0.785079 0.386286 1.205725 0.117 Uiso 1 1 calc R U . . .
C65 C 0.77606(12) 0.47701(14) 1.4403(2) 0.0463(7) Uani 1 1 d . . . . .
H51 H 0.801936 0.507063 1.490398 0.069 Uiso 1 1 calc R U . . .
H52 H 0.765999 0.437212 1.483629 0.069 Uiso 1 1 calc R U . . .
H53 H 0.741315 0.502388 1.409992 0.069 Uiso 1 1 calc R U . . .
C66 C 0.88853(9) 0.55033(10) 0.71012(17) 0.0228(5) Uani 1 1 d . . . . .
C67 C 0.49613(9) 0.61203(11) 0.63036(18) 0.0277(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C67 1.403(3) . ?
N1 C7 1.407(3) . ?
N1 C6 1.431(3) . ?
O1 C67 1.211(3) . ?
N2 C18 1.347(3) . ?
N2 C14 1.348(3) . ?
O2 C7 1.210(2) . ?
N3 C23 1.344(3) . ?
N3 C27 1.350(3) . ?
O3 C66 1.207(2) . ?
N4 C66 1.398(3) . ?
N4 C41 1.409(3) . ?
N4 C40 1.431(3) . ?
O4 C41 1.209(2) . ?
C1 C6 1.381(3) . ?
C1 C2 1.392(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.383(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.377(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.378(4) . ?
C4 H4 0.9500 . ?
N5 C48 1.341(3) . ?
N5 C52 1.342(3) . ?
C5 C6 1.386(3) . ?
C5 H5 0.9500 . ?
N6 C61 1.343(3) . ?
N6 C57 1.343(3) . ?
C7 C8 1.489(3) . ?
C8 C9 1.396(3) . ?
C8 C13 1.398(3) . ?
C9 C10 1.401(3) . ?
C9 C23 1.483(3) . ?
C10 C11 1.376(3) . ?
C10 H6 0.9500 . ?
C11 C12 1.405(3) . ?
C11 H7 0.9500 . ?
C12 C13 1.393(3) . ?
C12 C14 1.496(3) . ?
C13 C67 1.492(3) . ?
C14 C15 1.385(3) . ?
C15 C16 1.379(3) . ?
C15 H8 0.9500 . ?
C16 C17 1.382(3) . ?
C16 H9 0.9500 . ?
C17 C18 1.389(3) . ?
C17 H10 0.9500 . ?
C18 C19 1.528(3) . ?
C19 C22 1.529(3) . ?
C19 C20 1.532(3) . ?
C19 C21 1.540(3) . ?
C20 H27 0.9800 . ?
C20 H28 0.9800 . ?
C20 H29 0.9800 . ?
C21 H30 0.9800 . ?
C21 H31 0.9800 . ?
C21 H32 0.9800 . ?
C22 H33 0.9800 . ?
C22 H34 0.9800 . ?
C22 H35 0.9800 . ?
C23 C24 1.391(3) . ?
C24 C25 1.383(3) . ?
C24 H11 0.9500 . ?
C25 C26 1.381(3) . ?
C25 H12 0.9500 . ?
C26 C27 1.389(3) . ?
C26 H13 0.9500 . ?
C27 C28 1.526(3) . ?
C28 C30 1.513(4) . ?
C28 C31 1.513(4) . ?
C28 C29 1.516(4) . ?
C29 H54 0.9800 . ?
C29 H55 0.9800 . ?
C29 H56 0.9800 . ?
C30 H57 0.9800 . ?
C30 H58 0.9800 . ?
C30 H59 0.9800 . ?
C31 H60 0.9800 . ?
C31 H61 0.9800 . ?
C31 H62 0.9800 . ?
C35 C36 1.381(3) . ?
C35 C40 1.385(3) . ?
C35 H14 0.9500 . ?
C36 C37 1.371(3) . ?
C36 H15 0.9500 . ?
C37 C38 1.383(3) . ?
C37 H16 0.9500 . ?
C38 C39 1.396(3) . ?
C38 H17 0.9500 . ?
C39 C40 1.372(3) . ?
C39 H18 0.9500 . ?
C41 C42 1.493(3) . ?
C42 C43 1.398(3) . ?
C42 C47 1.401(3) . ?
C43 C44 1.401(3) . ?
C43 C57 1.492(3) . ?
C44 C45 1.379(3) . ?
C44 H19 0.9500 . ?
C45 C46 1.403(3) . ?
C45 H20 0.9500 . ?
C46 C47 1.383(3) . ?
C46 C48 1.486(3) . ?
C47 C66 1.491(3) . ?
C48 C49 1.391(3) . ?
C49 C50 1.375(3) . ?
C49 H21 0.9500 . ?
C50 C51 1.385(3) . ?
C50 H22 0.9500 . ?
C51 C52 1.391(3) . ?
C51 H23 0.9500 . ?
C52 C53 1.527(3) . ?
C53 C55 1.529(3) . ?
C53 C56 1.531(3) . ?
C53 C54 1.531(3) . ?
C54 H36 0.9800 . ?
C54 H37 0.9800 . ?
C54 H38 0.9800 . ?
C55 H39 0.9800 . ?
C55 H40 0.9800 . ?
C55 H41 0.9800 . ?
C56 H42 0.9800 . ?
C56 H43 0.9800 . ?
C56 H44 0.9800 . ?
C57 C58 1.386(3) . ?
C58 C59 1.374(3) . ?
C58 H24 0.9500 . ?
C59 C60 1.383(3) . ?
C59 H25 0.9500 . ?
C60 C61 1.395(3) . ?
C60 H26 0.9500 . ?
C61 C62 1.529(3) . ?
C62 C64 1.522(3) . ?
C62 C65 1.529(3) . ?
C62 C63 1.543(4) . ?
C63 H45 0.9800 . ?
C63 H46 0.9800 . ?
C63 H47 0.9800 . ?
C64 H48 0.9800 . ?
C64 H49 0.9800 . ?
C64 H50 0.9800 . ?
C65 H51 0.9800 . ?
C65 H52 0.9800 . ?
C65 H53 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C67 N1 C7 111.78(18) . . ?
C67 N1 C6 124.56(17) . . ?
C7 N1 C6 123.66(17) . . ?
C18 N2 C14 118.84(18) . . ?
C23 N3 C27 118.88(18) . . ?
C66 N4 C41 111.79(16) . . ?
C66 N4 C40 123.07(16) . . ?
C41 N4 C40 125.12(17) . . ?
C6 C1 C2 119.3(2) . . ?
C6 C1 H1 120.3 . . ?
C2 C1 H1 120.3 . . ?
C3 C2 C1 119.4(3) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C48 N5 C52 119.16(18) . . ?
C4 C5 C6 118.9(2) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C61 N6 C57 119.17(18) . . ?
C1 C6 C5 121.2(2) . . ?
C1 C6 N1 119.4(2) . . ?
C5 C6 N1 119.4(2) . . ?
O2 C7 N1 124.2(2) . . ?
O2 C7 C8 130.1(2) . . ?
N1 C7 C8 105.70(17) . . ?
C9 C8 C13 121.99(19) . . ?
C9 C8 C7 129.35(18) . . ?
C13 C8 C7 108.54(18) . . ?
C8 C9 C10 115.81(19) . . ?
C8 C9 C23 125.86(19) . . ?
C10 C9 C23 118.3(2) . . ?
C11 C10 C9 122.2(2) . . ?
C11 C10 H6 118.9 . . ?
C9 C10 H6 118.9 . . ?
C10 C11 C12 122.2(2) . . ?
C10 C11 H7 118.9 . . ?
C12 C11 H7 118.9 . . ?
C13 C12 C11 115.85(19) . . ?
C13 C12 C14 127.1(2) . . ?
C11 C12 C14 116.98(19) . . ?
C12 C13 C8 121.8(2) . . ?
C12 C13 C67 130.56(19) . . ?
C8 C13 C67 107.66(18) . . ?
N2 C14 C15 122.91(19) . . ?
N2 C14 C12 112.70(18) . . ?
C15 C14 C12 124.3(2) . . ?
C16 C15 C14 117.9(2) . . ?
C16 C15 H8 121.1 . . ?
C14 C15 H8 121.1 . . ?
C15 C16 C17 119.7(2) . . ?
C15 C16 H9 120.1 . . ?
C17 C16 H9 120.1 . . ?
C16 C17 C18 119.5(2) . . ?
C16 C17 H10 120.2 . . ?
C18 C17 H10 120.2 . . ?
N2 C18 C17 121.0(2) . . ?
N2 C18 C19 114.30(18) . . ?
C17 C18 C19 124.70(19) . . ?
C18 C19 C22 109.45(19) . . ?
C18 C19 C20 111.96(19) . . ?
C22 C19 C20 109.50(19) . . ?
C18 C19 C21 106.93(18) . . ?
C22 C19 C21 109.8(2) . . ?
C20 C19 C21 109.19(19) . . ?
C19 C20 H27 109.5 . . ?
C19 C20 H28 109.5 . . ?
H27 C20 H28 109.5 . . ?
C19 C20 H29 109.5 . . ?
H27 C20 H29 109.5 . . ?
H28 C20 H29 109.5 . . ?
C19 C21 H30 109.5 . . ?
C19 C21 H31 109.5 . . ?
H30 C21 H31 109.5 . . ?
C19 C21 H32 109.5 . . ?
H30 C21 H32 109.5 . . ?
H31 C21 H32 109.5 . . ?
C19 C22 H33 109.5 . . ?
C19 C22 H34 109.5 . . ?
H33 C22 H34 109.5 . . ?
C19 C22 H35 109.5 . . ?
H33 C22 H35 109.5 . . ?
H34 C22 H35 109.5 . . ?
N3 C23 C24 122.99(19) . . ?
N3 C23 C9 114.52(18) . . ?
C24 C23 C9 122.3(2) . . ?
C25 C24 C23 117.9(2) . . ?
C25 C24 H11 121.1 . . ?
C23 C24 H11 121.1 . . ?
C26 C25 C24 119.5(2) . . ?
C26 C25 H12 120.2 . . ?
C24 C25 H12 120.2 . . ?
C25 C26 C27 119.8(2) . . ?
C25 C26 H13 120.1 . . ?
C27 C26 H13 120.1 . . ?
N3 C27 C26 121.0(2) . . ?
N3 C27 C28 115.52(18) . . ?
C26 C27 C28 123.5(2) . . ?
C30 C28 C31 110.5(3) . . ?
C30 C28 C29 108.6(3) . . ?
C31 C28 C29 109.1(3) . . ?
C30 C28 C27 112.0(2) . . ?
C31 C28 C27 107.1(2) . . ?
C29 C28 C27 109.5(2) . . ?
C28 C29 H54 109.5 . . ?
C28 C29 H55 109.5 . . ?
H54 C29 H55 109.5 . . ?
C28 C29 H56 109.5 . . ?
H54 C29 H56 109.5 . . ?
H55 C29 H56 109.5 . . ?
C28 C30 H57 109.5 . . ?
C28 C30 H58 109.5 . . ?
H57 C30 H58 109.5 . . ?
C28 C30 H59 109.5 . . ?
H57 C30 H59 109.5 . . ?
H58 C30 H59 109.5 . . ?
C28 C31 H60 109.5 . . ?
C28 C31 H61 109.5 . . ?
H60 C31 H61 109.5 . . ?
C28 C31 H62 109.5 . . ?
H60 C31 H62 109.5 . . ?
H61 C31 H62 109.5 . . ?
C36 C35 C40 119.6(2) . . ?
C36 C35 H14 120.2 . . ?
C40 C35 H14 120.2 . . ?
C37 C36 C35 120.3(2) . . ?
C37 C36 H15 119.9 . . ?
C35 C36 H15 119.8 . . ?
C36 C37 C38 120.0(2) . . ?
C36 C37 H16 120.0 . . ?
C38 C37 H16 120.0 . . ?
C37 C38 C39 120.1(2) . . ?
C37 C38 H17 119.9 . . ?
C39 C38 H17 119.9 . . ?
C40 C39 C38 119.2(2) . . ?
C40 C39 H18 120.4 . . ?
C38 C39 H18 120.4 . . ?
C39 C40 C35 120.7(2) . . ?
C39 C40 N4 120.30(19) . . ?
C35 C40 N4 118.87(19) . . ?
O4 C41 N4 123.36(18) . . ?
O4 C41 C42 130.60(18) . . ?
N4 C41 C42 106.04(17) . . ?
C43 C42 C47 121.24(19) . . ?
C43 C42 C41 130.66(19) . . ?
C47 C42 C41 107.75(17) . . ?
C42 C43 C44 115.68(18) . . ?
C42 C43 C57 126.13(18) . . ?
C44 C43 C57 118.17(17) . . ?
C45 C44 C43 122.67(19) . . ?
C45 C44 H19 118.7 . . ?
C43 C44 H19 118.7 . . ?
C44 C45 C46 121.7(2) . . ?
C44 C45 H20 119.1 . . ?
C46 C45 H20 119.1 . . ?
C47 C46 C45 115.84(18) . . ?
C47 C46 C48 125.63(18) . . ?
C45 C46 C48 118.46(18) . . ?
C46 C47 C42 122.76(18) . . ?
C46 C47 C66 128.59(18) . . ?
C42 C47 C66 108.32(17) . . ?
N5 C48 C49 122.68(19) . . ?
N5 C48 C46 113.85(18) . . ?
C49 C48 C46 123.43(19) . . ?
C50 C49 C48 118.3(2) . . ?
C50 C49 H21 120.9 . . ?
C48 C49 H21 120.9 . . ?
C49 C50 C51 119.2(2) . . ?
C49 C50 H22 120.4 . . ?
C51 C50 H22 120.4 . . ?
C50 C51 C52 119.8(2) . . ?
C50 C51 H23 120.1 . . ?
C52 C51 H23 120.1 . . ?
N5 C52 C51 120.9(2) . . ?
N5 C52 C53 115.21(19) . . ?
C51 C52 C53 123.80(19) . . ?
C52 C53 C55 107.49(17) . . ?
C52 C53 C56 109.69(17) . . ?
C55 C53 C56 108.9(2) . . ?
C52 C53 C54 111.5(2) . . ?
C55 C53 C54 110.29(18) . . ?
C56 C53 C54 108.91(18) . . ?
C53 C54 H36 109.5 . . ?
C53 C54 H37 109.5 . . ?
H36 C54 H37 109.5 . . ?
C53 C54 H38 109.5 . . ?
H36 C54 H38 109.5 . . ?
H37 C54 H38 109.5 . . ?
C53 C55 H39 109.5 . . ?
C53 C55 H40 109.5 . . ?
H39 C55 H40 109.5 . . ?
C53 C55 H41 109.5 . . ?
H39 C55 H41 109.5 . . ?
H40 C55 H41 109.5 . . ?
C53 C56 H42 109.5 . . ?
C53 C56 H43 109.5 . . ?
H42 C56 H43 109.5 . . ?
C53 C56 H44 109.5 . . ?
H42 C56 H44 109.5 . . ?
H43 C56 H44 109.5 . . ?
N6 C57 C58 122.56(19) . . ?
N6 C57 C43 114.23(17) . . ?
C58 C57 C43 123.19(18) . . ?
C59 C58 C57 118.3(2) . . ?
C59 C58 H24 120.9 . . ?
C57 C58 H24 120.9 . . ?
C58 C59 C60 119.7(2) . . ?
C58 C59 H25 120.1 . . ?
C60 C59 H25 120.1 . . ?
C59 C60 C61 119.1(2) . . ?
C59 C60 H26 120.4 . . ?
C61 C60 H26 120.4 . . ?
N6 C61 C60 121.0(2) . . ?
N6 C61 C62 115.16(18) . . ?
C60 C61 C62 123.80(19) . . ?
C64 C62 C61 108.97(19) . . ?
C64 C62 C65 108.9(2) . . ?
C61 C62 C65 111.8(2) . . ?
C64 C62 C63 109.7(3) . . ?
C61 C62 C63 109.4(2) . . ?
C65 C62 C63 108.1(2) . . ?
C62 C63 H45 109.5 . . ?
C62 C63 H46 109.5 . . ?
H45 C63 H46 109.5 . . ?
C62 C63 H47 109.5 . . ?
H45 C63 H47 109.5 . . ?
H46 C63 H47 109.5 . . ?
C62 C64 H48 109.5 . . ?
C62 C64 H49 109.5 . . ?
H48 C64 H49 109.5 . . ?
C62 C64 H50 109.5 . . ?
H48 C64 H50 109.5 . . ?
H49 C64 H50 109.5 . . ?
C62 C65 H51 109.5 . . ?
C62 C65 H52 109.5 . . ?
H51 C65 H52 109.5 . . ?
C62 C65 H53 109.5 . . ?
H51 C65 H53 109.5 . . ?
H52 C65 H53 109.5 . . ?
O3 C66 N4 124.12(18) . . ?
O3 C66 C47 129.79(19) . . ?
N4 C66 C47 106.07(16) . . ?
O1 C67 N1 124.1(2) . . ?
O1 C67 C13 129.8(2) . . ?
N1 C67 C13 106.16(17) . . ?

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 -0.6(3) . . . . ?
C1 C2 C3 C4 1.9(4) . . . . ?
C2 C3 C4 C5 -1.4(4) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C2 C1 C6 C5 -1.1(3) . . . . ?
C2 C1 C6 N1 179.6(2) . . . . ?
C4 C5 C6 C1 1.6(3) . . . . ?
C4 C5 C6 N1 -179.1(2) . . . . ?
C67 N1 C6 C1 -58.9(3) . . . . ?
C7 N1 C6 C1 122.0(2) . . . . ?
C67 N1 C6 C5 121.8(2) . . . . ?
C7 N1 C6 C5 -57.4(3) . . . . ?
C67 N1 C7 O2 -179.8(2) . . . . ?
C6 N1 C7 O2 -0.6(3) . . . . ?
C67 N1 C7 C8 -0.6(2) . . . . ?
C6 N1 C7 C8 178.65(19) . . . . ?
O2 C7 C8 C9 1.1(4) . . . . ?
N1 C7 C8 C9 -178.1(2) . . . . ?
O2 C7 C8 C13 177.1(2) . . . . ?
N1 C7 C8 C13 -2.0(2) . . . . ?
C13 C8 C9 C10 -2.8(3) . . . . ?
C7 C8 C9 C10 172.7(2) . . . . ?
C13 C8 C9 C23 175.12(19) . . . . ?
C7 C8 C9 C23 -9.3(3) . . . . ?
C8 C9 C10 C11 4.0(3) . . . . ?
C23 C9 C10 C11 -174.1(2) . . . . ?
C9 C10 C11 C12 -1.4(3) . . . . ?
C10 C11 C12 C13 -2.6(3) . . . . ?
C10 C11 C12 C14 175.7(2) . . . . ?
C11 C12 C13 C8 3.7(3) . . . . ?
C14 C12 C13 C8 -174.3(2) . . . . ?
C11 C12 C13 C67 -177.7(2) . . . . ?
C14 C12 C13 C67 4.2(4) . . . . ?
C9 C8 C13 C12 -1.1(3) . . . . ?
C7 C8 C13 C12 -177.47(19) . . . . ?
C9 C8 C13 C67 -179.91(19) . . . . ?
C7 C8 C13 C67 3.7(2) . . . . ?
C18 N2 C14 C15 -0.1(3) . . . . ?
C18 N2 C14 C12 176.44(18) . . . . ?
C13 C12 C14 N2 137.4(2) . . . . ?
C11 C12 C14 N2 -40.6(3) . . . . ?
C13 C12 C14 C15 -46.1(3) . . . . ?
C11 C12 C14 C15 135.9(2) . . . . ?
N2 C14 C15 C16 2.7(3) . . . . ?
C12 C14 C15 C16 -173.5(2) . . . . ?
C14 C15 C16 C17 -2.5(3) . . . . ?
C15 C16 C17 C18 0.0(3) . . . . ?
C14 N2 C18 C17 -2.6(3) . . . . ?
C14 N2 C18 C19 176.26(19) . . . . ?
C16 C17 C18 N2 2.6(3) . . . . ?
C16 C17 C18 C19 -176.1(2) . . . . ?
N2 C18 C19 C22 56.2(2) . . . . ?
C17 C18 C19 C22 -125.1(2) . . . . ?
N2 C18 C19 C20 177.76(19) . . . . ?
C17 C18 C19 C20 -3.5(3) . . . . ?
N2 C18 C19 C21 -62.7(2) . . . . ?
C17 C18 C19 C21 116.1(2) . . . . ?
C27 N3 C23 C24 1.1(3) . . . . ?
C27 N3 C23 C9 176.27(18) . . . . ?
C8 C9 C23 N3 141.1(2) . . . . ?
C10 C9 C23 N3 -41.0(3) . . . . ?
C8 C9 C23 C24 -43.7(3) . . . . ?
C10 C9 C23 C24 134.2(2) . . . . ?
N3 C23 C24 C25 -0.5(3) . . . . ?
C9 C23 C24 C25 -175.3(2) . . . . ?
C23 C24 C25 C26 -0.3(3) . . . . ?
C24 C25 C26 C27 0.5(3) . . . . ?
C23 N3 C27 C26 -0.8(3) . . . . ?
C23 N3 C27 C28 -178.0(2) . . . . ?
C25 C26 C27 N3 0.0(3) . . . . ?
C25 C26 C27 C28 177.0(2) . . . . ?
N3 C27 C28 C30 -165.1(3) . . . . ?
C26 C27 C28 C30 17.8(4) . . . . ?
N3 C27 C28 C31 73.6(3) . . . . ?
C26 C27 C28 C31 -103.5(3) . . . . ?
N3 C27 C28 C29 -44.5(3) . . . . ?
C26 C27 C28 C29 138.3(3) . . . . ?
C40 C35 C36 C37 -0.5(3) . . . . ?
C35 C36 C37 C38 -0.7(3) . . . . ?
C36 C37 C38 C39 1.2(3) . . . . ?
C37 C38 C39 C40 -0.5(3) . . . . ?
C38 C39 C40 C35 -0.7(3) . . . . ?
C38 C39 C40 N4 -177.1(2) . . . . ?
C36 C35 C40 C39 1.2(3) . . . . ?
C36 C35 C40 N4 177.70(19) . . . . ?
C66 N4 C40 C39 122.9(2) . . . . ?
C41 N4 C40 C39 -58.9(3) . . . . ?
C66 N4 C40 C35 -53.6(3) . . . . ?
C41 N4 C40 C35 124.6(2) . . . . ?
C66 N4 C41 O4 179.71(19) . . . . ?
C40 N4 C41 O4 1.4(3) . . . . ?
C66 N4 C41 C42 -0.9(2) . . . . ?
C40 N4 C41 C42 -179.23(17) . . . . ?
O4 C41 C42 C43 5.8(4) . . . . ?
N4 C41 C42 C43 -173.5(2) . . . . ?
O4 C41 C42 C47 178.9(2) . . . . ?
N4 C41 C42 C47 -0.4(2) . . . . ?
C47 C42 C43 C44 -2.1(3) . . . . ?
C41 C42 C43 C44 170.15(19) . . . . ?
C47 C42 C43 C57 179.65(19) . . . . ?
C41 C42 C43 C57 -8.1(3) . . . . ?
C42 C43 C44 C45 0.8(3) . . . . ?
C57 C43 C44 C45 179.15(19) . . . . ?
C43 C44 C45 C46 1.4(3) . . . . ?
C44 C45 C46 C47 -2.1(3) . . . . ?
C44 C45 C46 C48 -179.39(19) . . . . ?
C45 C46 C47 C42 0.8(3) . . . . ?
C48 C46 C47 C42 177.80(19) . . . . ?
C45 C46 C47 C66 -171.9(2) . . . . ?
C48 C46 C47 C66 5.2(3) . . . . ?
C43 C42 C47 C46 1.4(3) . . . . ?
C41 C42 C47 C46 -172.45(18) . . . . ?
C43 C42 C47 C66 175.34(18) . . . . ?
C41 C42 C47 C66 1.5(2) . . . . ?
C52 N5 C48 C49 -1.4(3) . . . . ?
C52 N5 C48 C46 -179.08(17) . . . . ?
C47 C46 C48 N5 -133.1(2) . . . . ?
C45 C46 C48 N5 43.8(3) . . . . ?
C47 C46 C48 C49 49.2(3) . . . . ?
C45 C46 C48 C49 -133.8(2) . . . . ?
N5 C48 C49 C50 0.8(3) . . . . ?
C46 C48 C49 C50 178.31(19) . . . . ?
C48 C49 C50 C51 0.0(3) . . . . ?
C49 C50 C51 C52 -0.2(3) . . . . ?
C48 N5 C52 C51 1.1(3) . . . . ?
C48 N5 C52 C53 -175.82(17) . . . . ?
C50 C51 C52 N5 -0.3(3) . . . . ?
C50 C51 C52 C53 176.32(19) . . . . ?
N5 C52 C53 C55 80.3(2) . . . . ?
C51 C52 C53 C55 -96.5(2) . . . . ?
N5 C52 C53 C56 -38.0(3) . . . . ?
C51 C52 C53 C56 145.2(2) . . . . ?
N5 C52 C53 C54 -158.70(17) . . . . ?
C51 C52 C53 C54 24.5(3) . . . . ?
C61 N6 C57 C58 2.7(3) . . . . ?
C61 N6 C57 C43 -179.02(17) . . . . ?
C42 C43 C57 N6 141.6(2) . . . . ?
C44 C43 C57 N6 -36.6(3) . . . . ?
C42 C43 C57 C58 -40.1(3) . . . . ?
C44 C43 C57 C58 141.7(2) . . . . ?
N6 C57 C58 C59 -2.5(3) . . . . ?
C43 C57 C58 C59 179.4(2) . . . . ?
C57 C58 C59 C60 0.7(3) . . . . ?
C58 C59 C60 C61 0.6(3) . . . . ?
C57 N6 C61 C60 -1.2(3) . . . . ?
C57 N6 C61 C62 178.64(18) . . . . ?
C59 C60 C61 N6 -0.4(3) . . . . ?
C59 C60 C61 C62 179.7(2) . . . . ?
N6 C61 C62 C64 -59.3(3) . . . . ?
C60 C61 C62 C64 120.6(3) . . . . ?
N6 C61 C62 C65 -179.7(2) . . . . ?
C60 C61 C62 C65 0.1(3) . . . . ?
N6 C61 C62 C63 60.6(2) . . . . ?
C60 C61 C62 C63 -119.6(2) . . . . ?
C41 N4 C66 O3 -179.5(2) . . . . ?
C40 N4 C66 O3 -1.2(3) . . . . ?
C41 N4 C66 C47 1.8(2) . . . . ?
C40 N4 C66 C47 -179.84(17) . . . . ?
C46 C47 C66 O3 -7.1(4) . . . . ?
C42 C47 C66 O3 179.4(2) . . . . ?
C46 C47 C66 N4 171.5(2) . . . . ?
C42 C47 C66 N4 -2.0(2) . . . . ?
C7 N1 C67 O1 -177.7(2) . . . . ?
C6 N1 C67 O1 3.1(3) . . . . ?
C7 N1 C67 C13 2.8(2) . . . . ?
C6 N1 C67 C13 -176.44(19) . . . . ?
C12 C13 C67 O1 -2.2(4) . . . . ?
C8 C13 C67 O1 176.5(2) . . . . ?
C12 C13 C67 N1 177.3(2) . . . . ?
C8 C13 C67 N1 -4.0(2) . . . . ?

_refine_diff_density_max         0.630
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.043



