# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2343914'
loop_
_audit_author_name
_audit_author_address
'HIroshi Aoyama'
;Juntendo University
Japan
;
_audit_update_record             
;
2024-03-28 deposited with the CCDC.	2024-07-05 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C38 H37 O P'
_chemical_formula_moiety         'C38 H37 O P'
_chemical_formula_weight         540.68
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   9.79364(19)
_cell_length_b                   10.5919(2)
_cell_length_c                   14.5081(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 95.211(7)
_cell_angle_gamma                90.0000
_cell_volume                     1498.76(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    15923
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      68.22
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.830
_exptl_crystal_size_mid          0.810
_exptl_crystal_size_min          0.800
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576.00
_exptl_absorpt_coefficient_mu    1.018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.336
_exptl_absorpt_correction_T_max  0.443

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            15526
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_theta_max         68.221
_diffrn_reflns_theta_min         3.059
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             5305
_reflns_number_gt                5125
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.832
_reflns_Friedel_fraction_max     0.934
_reflns_Friedel_fraction_full    0.937

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1160
_refine_ls_wR_factor_gt          0.1154
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         5305
_refine_ls_number_parameters     362
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0723P)²+0.1487P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.045
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.41
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 2151 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(11)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
P P 0.2955 0.4335
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
P1 P 0.86723(7) 0.22925(7) 0.69555(5) 0.02255(18) Uani 1 1 d . . . . .
O1 O 0.4166(3) 0.5418(2) 0.76785(19) 0.0420(6) Uani 1 1 d . . . . .
H1 H 0.475094 0.486941 0.777996 0.050 Uiso 1 1 calc R U . . .
C1 C 0.7054(3) 0.2390(3) 0.74927(18) 0.0218(5) Uani 1 1 d . . . . .
C2 C 0.6968(3) 0.2501(3) 0.84410(19) 0.0256(6) Uani 1 1 d . . . . .
H2 H 0.776817 0.256234 0.883629 0.031 Uiso 1 1 calc R U . . .
C3 C 0.5701(3) 0.2520(3) 0.88074(19) 0.0282(7) Uani 1 1 d . . . . .
C4 C 0.4518(3) 0.2460(3) 0.8205(2) 0.0282(6) Uani 1 1 d . . . . .
H4 H 0.366978 0.248383 0.844476 0.034 Uiso 1 1 calc R U . . .
C5 C 0.4565(3) 0.2367(3) 0.7248(2) 0.0266(6) Uani 1 1 d . . . . .
C6 C 0.5842(3) 0.2315(3) 0.69058(18) 0.0233(5) Uani 1 1 d . . . . .
H6 H 0.589287 0.222792 0.627191 0.028 Uiso 1 1 calc R U . . .
C7 C 0.5613(4) 0.2610(4) 0.9838(2) 0.0467(10) Uani 1 1 d . . . . .
H7A H 0.652075 0.264241 1.014831 0.056 Uiso 1 1 calc R U . . .
H7B H 0.512167 0.336121 0.997543 0.056 Uiso 1 1 calc R U . . .
H7C H 0.514053 0.188429 1.004587 0.056 Uiso 1 1 calc R U . . .
C8 C 0.3269(3) 0.2329(4) 0.6615(2) 0.0399(8) Uani 1 1 d . . . . .
H8A H 0.249408 0.237459 0.697385 0.048 Uiso 1 1 calc R U . . .
H8B H 0.325039 0.303288 0.619675 0.048 Uiso 1 1 calc R U . . .
H8C H 0.323227 0.155622 0.626787 0.048 Uiso 1 1 calc R U . . .
C9 C 0.9919(3) 0.2529(3) 0.7960(2) 0.0272(7) Uani 1 1 d . . . . .
C10 C 1.0328(3) 0.3705(3) 0.8314(2) 0.0301(7) Uani 1 1 d . . . . .
H10 H 1.000890 0.443258 0.800775 0.036 Uiso 1 1 calc R U . . .
C11 C 1.1211(3) 0.3808(4) 0.9125(2) 0.0364(8) Uani 1 1 d . . . . .
C12 C 1.1689(4) 0.5081(5) 0.9475(3) 0.0531(11) Uani 1 1 d . . . . .
H12A H 1.128148 0.572550 0.907384 0.064 Uiso 1 1 calc R U . . .
H12B H 1.142310 0.520405 1.008930 0.064 Uiso 1 1 calc R U . . .
H12C H 1.266963 0.512856 0.948578 0.064 Uiso 1 1 calc R U . . .
C13 C 1.1646(3) 0.2713(4) 0.9576(2) 0.0410(9) Uani 1 1 d . . . . .
H13 H 1.219836 0.277443 1.013039 0.049 Uiso 1 1 calc R U . . .
C14 C 1.1287(3) 0.1521(4) 0.9232(3) 0.0395(9) Uani 1 1 d . . . . .
C15 C 1.0426(3) 0.1443(4) 0.8415(2) 0.0330(7) Uani 1 1 d . . . . .
H15 H 1.018665 0.065500 0.816834 0.040 Uiso 1 1 calc R U . . .
C16 C 1.1859(4) 0.0336(5) 0.9707(3) 0.0613(13) Uani 1 1 d . . . . .
H16A H 1.242671 0.056286 1.025667 0.074 Uiso 1 1 calc R U . . .
H16B H 1.111712 -0.018633 0.987082 0.074 Uiso 1 1 calc R U . . .
H16C H 1.239519 -0.011859 0.929577 0.074 Uiso 1 1 calc R U . . .
C17 C 0.8706(3) 0.3823(3) 0.63639(18) 0.0221(6) Uani 1 1 d . . . . .
C18 C 0.9823(3) 0.4037(3) 0.5849(2) 0.0281(7) Uani 1 1 d . . . . .
H18 H 1.050545 0.342925 0.583243 0.034 Uiso 1 1 calc R U . . .
C19 C 0.9914(3) 0.5160(3) 0.5361(2) 0.0332(7) Uani 1 1 d . . . . .
H19 H 1.064874 0.529765 0.501026 0.040 Uiso 1 1 calc R U . . .
C20 C 0.8917(3) 0.6065(3) 0.5398(2) 0.0312(7) Uani 1 1 d . . . . .
H20 H 0.899584 0.681881 0.507925 0.037 Uiso 1 1 calc R U . . .
C21 C 0.7789(3) 0.5878(3) 0.5904(2) 0.0249(6) Uani 1 1 d . . . . .
C22 C 0.7699(3) 0.4743(3) 0.6375(2) 0.0221(6) Uani 1 1 d . . . . .
H22 H 0.694540 0.459600 0.670660 0.026 Uiso 1 1 calc R U . . .
C23 C 0.6713(3) 0.6874(3) 0.5905(2) 0.0256(7) Uani 1 1 d . . . . .
C24 C 0.5331(3) 0.6546(3) 0.57598(19) 0.0260(6) Uani 1 1 d . . . . .
H24 H 0.509301 0.570441 0.565638 0.031 Uiso 1 1 calc R U . . .
C25 C 0.4298(3) 0.7453(3) 0.57661(19) 0.0329(7) Uani 1 1 d . . . . .
C26 C 0.4691(4) 0.8711(3) 0.5728(2) 0.0378(8) Uani 1 1 d . . . . .
H26 H 0.403874 0.933154 0.557170 0.045 Uiso 1 1 calc R U . . .
C27 C 0.6051(4) 0.9038(3) 0.5924(2) 0.0383(8) Uani 1 1 d . . . . .
H27 H 0.629423 0.988708 0.592859 0.046 Uiso 1 1 calc R U . . .
C28 C 0.7069(4) 0.8131(3) 0.6116(2) 0.0318(7) Uani 1 1 d . . . . .
C29 C 0.8334(4) 0.8487(4) 0.6742(3) 0.0411(8) Uani 1 1 d . . . . .
H29A H 0.847220 0.939193 0.671351 0.049 Uiso 1 1 calc R U . . .
H29B H 0.912934 0.807750 0.652324 0.049 Uiso 1 1 calc R U . . .
C30 C 0.8203(5) 0.8086(5) 0.7781(3) 0.0541(11) Uani 1 1 d . . . . .
H30A H 0.866765 0.728634 0.789964 0.065 Uiso 1 1 calc R U . . .
H30B H 0.865927 0.871175 0.818902 0.065 Uiso 1 1 calc R U . . .
C31 C 0.6730(4) 0.7959(4) 0.8006(2) 0.0407(9) Uani 1 1 d . . . . .
C32 C 0.5841(5) 0.8978(4) 0.8023(2) 0.0470(10) Uani 1 1 d . . . . .
H32 H 0.618315 0.978021 0.816557 0.056 Uiso 1 1 calc R U . . .
C33 C 0.4445(5) 0.8798(4) 0.7829(2) 0.0428(9) Uani 1 1 d . . . . .
H33 H 0.386305 0.949016 0.783934 0.051 Uiso 1 1 calc R U . . .
C34 C 0.3887(4) 0.7619(3) 0.7621(2) 0.0378(8) Uani 1 1 d . . . . .
C35 C 0.4760(4) 0.6589(3) 0.7812(2) 0.0325(7) Uani 1 1 d . . . . .
C36 C 0.6154(4) 0.6745(3) 0.7995(2) 0.0338(8) Uani 1 1 d . . . . .
H36 H 0.671580 0.604456 0.811099 0.041 Uiso 1 1 calc R U . . .
C37 C 0.2577(4) 0.7476(4) 0.6997(3) 0.0477(10) Uani 1 1 d . . . . .
H37A H 0.207796 0.826823 0.697613 0.057 Uiso 1 1 calc R U . . .
H37B H 0.200640 0.683848 0.725029 0.057 Uiso 1 1 calc R U . . .
C38 C 0.2867(4) 0.7088(4) 0.5985(3) 0.0428(9) Uani 1 1 d . . . . .
H38A H 0.275521 0.618174 0.591481 0.051 Uiso 1 1 calc R U . . .
H38B H 0.220112 0.749400 0.554623 0.051 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2.5'

#==============================================================================
# MOLECULAR GEOMETRY

_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
P1 C1 1.832(3) . ?
P1 C9 1.831(3) . ?
P1 C17 1.836(3) . ?
O1 C35 1.376(4) . ?
O1 H1 0.8200 . ?
C1 C2 1.391(4) . ?
C1 C6 1.399(4) . ?
C2 C3 1.394(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(4) . ?
C3 C7 1.508(4) . ?
C4 C5 1.396(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(4) . ?
C5 C8 1.499(4) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.392(5) . ?
C9 C15 1.394(5) . ?
C10 C11 1.399(4) . ?
C10 H10 0.9300 . ?
C11 C13 1.380(5) . ?
C11 C12 1.501(6) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.391(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.394(5) . ?
C14 C16 1.514(6) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C22 1.387(4) . ?
C17 C18 1.399(4) . ?
C18 C19 1.391(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.372(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.395(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.390(4) . ?
C21 C23 1.492(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.394(5) . ?
C23 C28 1.403(4) . ?
C24 C25 1.396(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.390(5) . ?
C25 C38 1.515(5) . ?
C26 C27 1.381(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.395(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.516(5) . ?
C29 C30 1.582(5) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.513(6) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C32 1.388(6) . ?
C31 C36 1.403(5) . ?
C32 C33 1.384(6) . ?
C32 H32 0.9300 . ?
C33 C34 1.385(5) . ?
C33 H33 0.9300 . ?
C34 C35 1.398(5) . ?
C34 C37 1.510(5) . ?
C35 C36 1.377(5) . ?
C36 H36 0.9300 . ?
C37 C38 1.575(5) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?

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 P1 C9 101.20(12) . . ?
C1 P1 C17 101.66(13) . . ?
C9 P1 C17 102.26(14) . . ?
C35 O1 H1 109.5 . . ?
C2 C1 C6 118.9(2) . . ?
C2 C1 P1 123.9(2) . . ?
C6 C1 P1 117.2(2) . . ?
C3 C2 C1 120.9(3) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C4 C3 C2 118.7(3) . . ?
C4 C3 C7 120.5(3) . . ?
C2 C3 C7 120.8(3) . . ?
C3 C4 C5 121.9(3) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 118.1(3) . . ?
C6 C5 C8 121.3(3) . . ?
C4 C5 C8 120.6(3) . . ?
C5 C6 C1 121.5(2) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C15 119.0(3) . . ?
C10 C9 P1 124.4(2) . . ?
C15 C9 P1 116.6(3) . . ?
C9 C10 C11 121.0(3) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C13 C11 C10 118.3(3) . . ?
C13 C11 C12 121.4(3) . . ?
C10 C11 C12 120.3(4) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 C14 122.4(3) . . ?
C11 C13 H13 118.8 . . ?
C14 C13 H13 118.8 . . ?
C15 C14 C13 118.2(3) . . ?
C15 C14 C16 120.6(4) . . ?
C13 C14 C16 121.2(3) . . ?
C14 C15 C9 121.1(3) . . ?
C14 C15 H15 119.5 . . ?
C9 C15 H15 119.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C22 C17 C18 118.9(3) . . ?
C22 C17 P1 124.9(2) . . ?
C18 C17 P1 116.2(2) . . ?
C19 C18 C17 120.0(3) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C20 C19 C18 119.9(3) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 121.4(3) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
C22 C21 C20 118.0(3) . . ?
C22 C21 C23 122.4(3) . . ?
C20 C21 C23 119.6(3) . . ?
C17 C22 C21 121.7(3) . . ?
C17 C22 H22 119.2 . . ?
C21 C22 H22 119.2 . . ?
C24 C23 C28 119.2(3) . . ?
C24 C23 C21 120.0(3) . . ?
C28 C23 C21 120.6(3) . . ?
C25 C24 C23 121.5(3) . . ?
C25 C24 H24 119.3 . . ?
C23 C24 H24 119.3 . . ?
C26 C25 C24 117.1(3) . . ?
C26 C25 C38 121.2(3) . . ?
C24 C25 C38 120.7(3) . . ?
C27 C26 C25 119.9(3) . . ?
C27 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
C26 C27 C28 121.8(3) . . ?
C26 C27 H27 119.1 . . ?
C28 C27 H27 119.1 . . ?
C27 C28 C23 116.8(3) . . ?
C27 C28 C29 118.6(3) . . ?
C23 C28 C29 122.7(3) . . ?
C28 C29 C30 111.8(3) . . ?
C28 C29 H29A 109.2 . . ?
C30 C29 H29A 109.2 . . ?
C28 C29 H29B 109.2 . . ?
C30 C29 H29B 109.2 . . ?
H29A C29 H29B 107.9 . . ?
C31 C30 C29 113.0(3) . . ?
C31 C30 H30A 109.0 . . ?
C29 C30 H30A 109.0 . . ?
C31 C30 H30B 109.0 . . ?
C29 C30 H30B 109.0 . . ?
H30A C30 H30B 107.8 . . ?
C32 C31 C36 117.4(4) . . ?
C32 C31 C30 123.1(4) . . ?
C36 C31 C30 118.0(4) . . ?
C33 C32 C31 119.9(3) . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C32 C33 C34 122.1(4) . . ?
C32 C33 H33 118.9 . . ?
C34 C33 H33 118.9 . . ?
C33 C34 C35 116.0(4) . . ?
C33 C34 C37 121.2(3) . . ?
C35 C34 C37 120.8(3) . . ?
O1 C35 C36 122.3(3) . . ?
O1 C35 C34 115.6(3) . . ?
C36 C35 C34 121.5(3) . . ?
C35 C36 C31 120.2(3) . . ?
C35 C36 H36 119.9 . . ?
C31 C36 H36 119.9 . . ?
C34 C37 C38 111.7(3) . . ?
C34 C37 H37A 109.3 . . ?
C38 C37 H37A 109.3 . . ?
C34 C37 H37B 109.3 . . ?
C38 C37 H37B 109.3 . . ?
H37A C37 H37B 107.9 . . ?
C25 C38 C37 112.2(3) . . ?
C25 C38 H38A 109.2 . . ?
C37 C38 H38A 109.2 . . ?
C25 C38 H38B 109.2 . . ?
C37 C38 H38B 109.2 . . ?
H38A C38 H38B 107.9 . . ?

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
C9 P1 C1 C2 -5.0(3) . . . . ?
C17 P1 C1 C2 -110.2(3) . . . . ?
C9 P1 C1 C6 176.7(3) . . . . ?
C17 P1 C1 C6 71.5(3) . . . . ?
C6 C1 C2 C3 0.8(5) . . . . ?
P1 C1 C2 C3 -177.4(2) . . . . ?
C1 C2 C3 C4 -1.7(5) . . . . ?
C1 C2 C3 C7 178.6(3) . . . . ?
C2 C3 C4 C5 0.8(5) . . . . ?
C7 C3 C4 C5 -179.5(3) . . . . ?
C3 C4 C5 C6 0.9(5) . . . . ?
C3 C4 C5 C8 -178.8(3) . . . . ?
C4 C5 C6 C1 -1.8(5) . . . . ?
C8 C5 C6 C1 177.9(3) . . . . ?
C2 C1 C6 C5 1.0(5) . . . . ?
P1 C1 C6 C5 179.3(2) . . . . ?
C1 P1 C9 C10 -83.9(3) . . . . ?
C17 P1 C9 C10 20.8(3) . . . . ?
C1 P1 C9 C15 92.8(2) . . . . ?
C17 P1 C9 C15 -162.5(2) . . . . ?
C15 C9 C10 C11 -1.3(4) . . . . ?
P1 C9 C10 C11 175.3(2) . . . . ?
C9 C10 C11 C13 -1.4(5) . . . . ?
C9 C10 C11 C12 177.4(3) . . . . ?
C10 C11 C13 C14 2.9(5) . . . . ?
C12 C11 C13 C14 -175.8(4) . . . . ?
C11 C13 C14 C15 -1.8(5) . . . . ?
C11 C13 C14 C16 175.7(3) . . . . ?
C13 C14 C15 C9 -1.0(5) . . . . ?
C16 C14 C15 C9 -178.5(3) . . . . ?
C10 C9 C15 C14 2.5(4) . . . . ?
P1 C9 C15 C14 -174.4(3) . . . . ?
C1 P1 C17 C22 0.2(3) . . . . ?
C9 P1 C17 C22 -104.2(2) . . . . ?
C1 P1 C17 C18 -178.1(2) . . . . ?
C9 P1 C17 C18 77.6(2) . . . . ?
C22 C17 C18 C19 0.2(4) . . . . ?
P1 C17 C18 C19 178.5(2) . . . . ?
C17 C18 C19 C20 1.1(5) . . . . ?
C18 C19 C20 C21 -1.2(5) . . . . ?
C19 C20 C21 C22 0.1(5) . . . . ?
C19 C20 C21 C23 -178.4(3) . . . . ?
C18 C17 C22 C21 -1.3(4) . . . . ?
P1 C17 C22 C21 -179.5(2) . . . . ?
C20 C21 C22 C17 1.2(4) . . . . ?
C23 C21 C22 C17 179.7(3) . . . . ?
C22 C21 C23 C24 -45.5(4) . . . . ?
C20 C21 C23 C24 132.9(3) . . . . ?
C22 C21 C23 C28 129.9(3) . . . . ?
C20 C21 C23 C28 -51.6(4) . . . . ?
C28 C23 C24 C25 3.8(4) . . . . ?
C21 C23 C24 C25 179.3(3) . . . . ?
C23 C24 C25 C26 13.1(4) . . . . ?
C23 C24 C25 C38 -155.8(3) . . . . ?
C24 C25 C26 C27 -16.6(4) . . . . ?
C38 C25 C26 C27 152.2(3) . . . . ?
C25 C26 C27 C28 3.3(5) . . . . ?
C26 C27 C28 C23 13.6(5) . . . . ?
C26 C27 C28 C29 -151.2(3) . . . . ?
C24 C23 C28 C27 -16.9(4) . . . . ?
C21 C23 C28 C27 167.6(3) . . . . ?
C24 C23 C28 C29 147.3(3) . . . . ?
C21 C23 C28 C29 -28.2(5) . . . . ?
C27 C28 C29 C30 95.5(4) . . . . ?
C23 C28 C29 C30 -68.4(5) . . . . ?
C28 C29 C30 C31 -23.9(5) . . . . ?
C29 C30 C31 C32 -67.2(5) . . . . ?
C29 C30 C31 C36 98.4(4) . . . . ?
C36 C31 C32 C33 -14.0(5) . . . . ?
C30 C31 C32 C33 151.7(3) . . . . ?
C31 C32 C33 C34 0.5(5) . . . . ?
C32 C33 C34 C35 13.4(5) . . . . ?
C32 C33 C34 C37 -150.5(3) . . . . ?
C33 C34 C35 O1 174.6(3) . . . . ?
C37 C34 C35 O1 -21.3(5) . . . . ?
C33 C34 C35 C36 -14.1(5) . . . . ?
C37 C34 C35 C36 150.0(3) . . . . ?
O1 C35 C36 C31 171.7(3) . . . . ?
C34 C35 C36 C31 0.9(5) . . . . ?
C32 C31 C36 C35 13.3(5) . . . . ?
C30 C31 C36 C35 -153.2(3) . . . . ?
C33 C34 C37 C38 100.6(4) . . . . ?
C35 C34 C37 C38 -62.6(5) . . . . ?
C26 C25 C38 C37 -64.9(4) . . . . ?
C24 C25 C38 C37 103.5(4) . . . . ?
C34 C37 C38 C25 -23.1(5) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 2343921'
loop_
_audit_author_name
_audit_author_address
'Hiroshi Aoyama'
;Juntendo University
Japan
;
_audit_update_record             
;
2024-03-28 deposited with the CCDC.	2024-07-05 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C23 H21 N O4'
_chemical_formula_moiety         'C23 H21 N O4'
_chemical_formula_weight         375.42
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   9.2471(2)
_cell_length_b                   10.8522(3)
_cell_length_c                   11.3167(3)
_cell_angle_alpha                64.284(5)
_cell_angle_beta                 80.943(6)
_cell_angle_gamma                65.621(5)
_cell_volume                     931.62(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10540
_cell_measurement_theta_min      4.34
_cell_measurement_theta_max      68.27
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.280
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             396.00
_exptl_absorpt_coefficient_mu    0.747
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.612
_exptl_absorpt_correction_T_max  0.811

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      123
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            10684
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_theta_max         68.200
_diffrn_reflns_theta_min         4.338
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3323
_reflns_number_gt                3055
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1382
_refine_ls_wR_factor_gt          0.1355
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3323
_refine_ls_number_parameters     253
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0692P)²+0.7095P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.59
_refine_diff_density_min         -0.67
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.82217(18) 0.75806(16) -0.02181(14) 0.0365(4) Uani 1 1 d . . . . .
O2 O 1.22076(16) 0.43777(16) 0.21352(13) 0.0310(3) Uani 1 1 d . . . . .
O3 O 1.19263(17) 0.25867(15) 0.70323(13) 0.0305(3) Uani 1 1 d . . . . .
O4 O 1.39384(15) 0.05321(16) 0.69942(13) 0.0304(3) Uani 1 1 d . . . . .
N5 N 0.95791(17) 0.53676(17) 0.14060(14) 0.0211(3) Uani 1 1 d . . . . .
C1 C 1.0661(3) 0.7342(2) 0.0461(2) 0.0332(5) Uani 1 1 d . . . . .
H1A H 1.149777 0.655553 0.111436 0.040 Uiso 1 1 calc R U . . .
H1B H 1.111393 0.759830 -0.041394 0.040 Uiso 1 1 calc R U . . .
H1C H 1.020478 0.821986 0.066020 0.040 Uiso 1 1 calc R U . . .
C2 C 0.9391(2) 0.6812(2) 0.04976(17) 0.0252(4) Uani 1 1 d . . . . .
C3 C 0.8370(2) 0.4784(2) 0.17061(17) 0.0209(4) Uani 1 1 d . . . . .
C4 C 0.6914(2) 0.5371(2) 0.10735(18) 0.0263(4) Uani 1 1 d . . . . .
H4 H 0.657885 0.629904 0.033425 0.032 Uiso 1 1 calc R U . . .
C5 C 0.5963(2) 0.4550(2) 0.1563(2) 0.0300(5) Uani 1 1 d . . . . .
H5 H 0.495077 0.493761 0.116094 0.036 Uiso 1 1 calc R U . . .
C6 C 0.6457(2) 0.3180(2) 0.2624(2) 0.0304(5) Uani 1 1 d . . . . .
H6 H 0.579235 0.263481 0.293014 0.036 Uiso 1 1 calc R U . . .
C7 C 0.7922(2) 0.2603(2) 0.32391(18) 0.0264(4) Uani 1 1 d . . . . .
H7 H 0.826767 0.166286 0.396327 0.032 Uiso 1 1 calc R U . . .
C8 C 0.8872(2) 0.3417(2) 0.27828(17) 0.0212(4) Uani 1 1 d . . . . .
C9 C 1.0465(2) 0.3066(2) 0.32805(17) 0.0208(4) Uani 1 1 d . . . . .
C10 C 1.0924(2) 0.4308(2) 0.22382(17) 0.0216(4) Uani 1 1 d . . . . .
C11 C 1.1761(2) 0.1524(2) 0.34571(18) 0.0264(4) Uani 1 1 d . . . . .
H11A H 1.127494 0.081124 0.360399 0.032 Uiso 1 1 calc R U . . .
H11B H 1.242999 0.159737 0.267471 0.032 Uiso 1 1 calc R U . . .
C12 C 1.2717(2) 0.1055(2) 0.46332(18) 0.0245(4) Uani 1 1 d . . . . .
H12 H 1.369021 0.021479 0.490705 0.029 Uiso 1 1 calc R U . . .
C13 C 1.2058(2) 0.1943(2) 0.52555(17) 0.0214(4) Uani 1 1 d . . . . .
C14 C 1.0488(2) 0.31713(19) 0.46424(17) 0.0199(4) Uani 1 1 d . . . . .
H14 H 1.052455 0.414517 0.446160 0.024 Uiso 1 1 calc R U . . .
C15 C 0.9092(2) 0.29974(19) 0.55109(16) 0.0200(4) Uani 1 1 d . . . . .
C16 C 0.7715(2) 0.4250(2) 0.53550(18) 0.0245(4) Uani 1 1 d . . . . .
H16 H 0.765911 0.519004 0.470376 0.029 Uiso 1 1 calc R U . . .
C17 C 0.6424(2) 0.4143(2) 0.61378(19) 0.0291(4) Uani 1 1 d . . . . .
H17 H 0.549524 0.500864 0.602853 0.035 Uiso 1 1 calc R U . . .
C18 C 0.6483(2) 0.2779(2) 0.70784(19) 0.0298(4) Uani 1 1 d . . . . .
H18 H 0.559284 0.270538 0.760920 0.036 Uiso 1 1 calc R U . . .
C19 C 0.7845(2) 0.1521(2) 0.72446(19) 0.0277(4) Uani 1 1 d . . . . .
H19 H 0.788910 0.058182 0.789036 0.033 Uiso 1 1 calc R U . . .
C20 C 0.9146(2) 0.1631(2) 0.64671(18) 0.0235(4) Uani 1 1 d . . . . .
H20 H 1.008021 0.076568 0.658929 0.028 Uiso 1 1 calc R U . . .
C21 C 1.2614(2) 0.1750(2) 0.65025(17) 0.0232(4) Uani 1 1 d . . . . .
C22 C 1.4376(2) 0.0113(2) 0.83365(19) 0.0327(5) Uani 1 1 d . . . . .
H22A H 1.412568 0.101433 0.848277 0.039 Uiso 1 1 calc R U . . .
H22B H 1.553266 -0.047884 0.848760 0.039 Uiso 1 1 calc R U . . .
C23 C 1.3484(3) -0.0778(3) 0.9273(2) 0.0391(5) Uani 1 1 d . . . . .
H23A H 1.378140 -0.105873 1.017555 0.047 Uiso 1 1 calc R U . . .
H23B H 1.234035 -0.018534 0.912708 0.047 Uiso 1 1 calc R U . . .
H23C H 1.374416 -0.167515 0.913190 0.047 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2.5'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C2 1.211(2) . ?
O2 C10 1.204(2) . ?
O3 C21 1.210(2) . ?
O4 C21 1.340(2) . ?
O4 C22 1.456(2) . ?
N5 C2 1.406(2) . ?
N5 C10 1.416(2) . ?
N5 C3 1.430(2) . ?
C1 C2 1.495(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C3 C4 1.390(3) . ?
C3 C8 1.393(3) . ?
C4 C5 1.393(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.390(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.386(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.498(2) . ?
C9 C10 1.524(2) . ?
C9 C11 1.551(2) . ?
C9 C14 1.598(2) . ?
C11 C12 1.491(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.328(3) . ?
C12 H12 0.9500 . ?
C13 C21 1.478(3) . ?
C13 C14 1.511(2) . ?
C14 C15 1.519(2) . ?
C14 H14 1.0000 . ?
C15 C16 1.391(3) . ?
C15 C20 1.392(3) . ?
C16 C17 1.384(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.382(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.389(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C22 C23 1.495(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
C21 O4 C22 115.47(15) . . ?
C2 N5 C10 126.10(15) . . ?
C2 N5 C3 124.57(15) . . ?
C10 N5 C3 109.15(14) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 N5 119.66(18) . . ?
O1 C2 C1 122.38(18) . . ?
N5 C2 C1 117.96(17) . . ?
C4 C3 C8 121.37(17) . . ?
C4 C3 N5 129.40(17) . . ?
C8 C3 N5 109.21(15) . . ?
C3 C4 C5 117.56(18) . . ?
C3 C4 H4 121.2 . . ?
C5 C4 H4 121.2 . . ?
C6 C5 C4 121.60(18) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 120.12(18) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 119.14(18) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C3 120.19(17) . . ?
C7 C8 C9 129.64(17) . . ?
C3 C8 C9 110.17(16) . . ?
C8 C9 C10 102.36(14) . . ?
C8 C9 C11 116.08(15) . . ?
C10 C9 C11 110.91(14) . . ?
C8 C9 C14 116.12(14) . . ?
C10 C9 C14 106.22(14) . . ?
C11 C9 C14 104.81(14) . . ?
O2 C10 N5 125.77(17) . . ?
O2 C10 C9 126.13(16) . . ?
N5 C10 C9 108.10(14) . . ?
C12 C11 C9 104.62(15) . . ?
C12 C11 H11A 110.8 . . ?
C9 C11 H11A 110.8 . . ?
C12 C11 H11B 110.8 . . ?
C9 C11 H11B 110.8 . . ?
H11A C11 H11B 108.9 . . ?
C13 C12 C11 112.52(16) . . ?
C13 C12 H12 123.7 . . ?
C11 C12 H12 123.7 . . ?
C12 C13 C21 127.07(17) . . ?
C12 C13 C14 113.21(16) . . ?
C21 C13 C14 119.40(16) . . ?
C13 C14 C15 112.67(14) . . ?
C13 C14 C9 102.00(14) . . ?
C15 C14 C9 114.74(14) . . ?
C13 C14 H14 109.0 . . ?
C15 C14 H14 109.0 . . ?
C9 C14 H14 109.0 . . ?
C16 C15 C20 118.68(16) . . ?
C16 C15 C14 118.93(16) . . ?
C20 C15 C14 122.39(16) . . ?
C17 C16 C15 120.75(18) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C18 C17 C16 120.18(18) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 119.81(18) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C20 120.00(18) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C15 120.58(17) . . ?
C19 C20 H20 119.7 . . ?
C15 C20 H20 119.7 . . ?
O3 C21 O4 123.88(17) . . ?
O3 C21 C13 123.46(17) . . ?
O4 C21 C13 112.65(16) . . ?
O4 C22 C23 109.69(17) . . ?
O4 C22 H22A 109.7 . . ?
C23 C22 H22A 109.7 . . ?
O4 C22 H22B 109.7 . . ?
C23 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
C10 N5 C2 O1 175.28(17) . . . . ?
C3 N5 C2 O1 -10.1(3) . . . . ?
C10 N5 C2 C1 -5.0(3) . . . . ?
C3 N5 C2 C1 169.63(16) . . . . ?
C2 N5 C3 C4 10.7(3) . . . . ?
C10 N5 C3 C4 -173.88(18) . . . . ?
C2 N5 C3 C8 -170.86(16) . . . . ?
C10 N5 C3 C8 4.55(19) . . . . ?
C8 C3 C4 C5 0.6(3) . . . . ?
N5 C3 C4 C5 178.88(17) . . . . ?
C3 C4 C5 C6 -1.4(3) . . . . ?
C4 C5 C6 C7 1.0(3) . . . . ?
C5 C6 C7 C8 0.3(3) . . . . ?
C6 C7 C8 C3 -1.1(3) . . . . ?
C6 C7 C8 C9 178.71(17) . . . . ?
C4 C3 C8 C7 0.7(3) . . . . ?
N5 C3 C8 C7 -177.93(15) . . . . ?
C4 C3 C8 C9 -179.21(16) . . . . ?
N5 C3 C8 C9 2.21(19) . . . . ?
C7 C8 C9 C10 172.75(18) . . . . ?
C3 C8 C9 C10 -7.41(18) . . . . ?
C7 C8 C9 C11 51.8(3) . . . . ?
C3 C8 C9 C11 -128.35(16) . . . . ?
C7 C8 C9 C14 -72.0(2) . . . . ?
C3 C8 C9 C14 107.81(17) . . . . ?
C2 N5 C10 O2 -14.1(3) . . . . ?
C3 N5 C10 O2 170.57(17) . . . . ?
C2 N5 C10 C9 166.03(16) . . . . ?
C3 N5 C10 C9 -9.29(18) . . . . ?
C8 C9 C10 O2 -169.85(18) . . . . ?
C11 C9 C10 O2 -45.4(2) . . . . ?
C14 C9 C10 O2 67.9(2) . . . . ?
C8 C9 C10 N5 10.01(18) . . . . ?
C11 C9 C10 N5 134.45(15) . . . . ?
C14 C9 C10 N5 -112.21(15) . . . . ?
C8 C9 C11 C12 -145.11(16) . . . . ?
C10 C9 C11 C12 98.65(17) . . . . ?
C14 C9 C11 C12 -15.58(18) . . . . ?
C9 C11 C12 C13 9.3(2) . . . . ?
C11 C12 C13 C21 175.19(17) . . . . ?
C11 C12 C13 C14 1.7(2) . . . . ?
C12 C13 C14 C15 112.00(18) . . . . ?
C21 C13 C14 C15 -62.0(2) . . . . ?
C12 C13 C14 C9 -11.54(19) . . . . ?
C21 C13 C14 C9 174.46(15) . . . . ?
C8 C9 C14 C13 145.64(15) . . . . ?
C10 C9 C14 C13 -101.34(15) . . . . ?
C11 C9 C14 C13 16.13(17) . . . . ?
C8 C9 C14 C15 23.5(2) . . . . ?
C10 C9 C14 C15 136.53(15) . . . . ?
C11 C9 C14 C15 -105.99(17) . . . . ?
C13 C14 C15 C16 155.51(16) . . . . ?
C9 C14 C15 C16 -88.4(2) . . . . ?
C13 C14 C15 C20 -23.9(2) . . . . ?
C9 C14 C15 C20 92.3(2) . . . . ?
C20 C15 C16 C17 0.3(3) . . . . ?
C14 C15 C16 C17 -179.15(17) . . . . ?
C15 C16 C17 C18 -0.8(3) . . . . ?
C16 C17 C18 C19 0.6(3) . . . . ?
C17 C18 C19 C20 0.0(3) . . . . ?
C18 C19 C20 C15 -0.5(3) . . . . ?
C16 C15 C20 C19 0.4(3) . . . . ?
C14 C15 C20 C19 179.75(17) . . . . ?
C22 O4 C21 O3 10.2(3) . . . . ?
C22 O4 C21 C13 -168.35(16) . . . . ?
C12 C13 C21 O3 -177.96(18) . . . . ?
C14 C13 C21 O3 -4.9(3) . . . . ?
C12 C13 C21 O4 0.6(3) . . . . ?
C14 C13 C21 O4 173.68(15) . . . . ?
C21 O4 C22 C23 83.9(2) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2343919'
loop_
_audit_author_name
_audit_author_address
'HIroshi Aoyama'
;Juntendo University
Japan
;
_audit_update_record             
;
2024-03-28 deposited with the CCDC.	2024-07-05 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C23 H21 N O4'
_chemical_formula_moiety         'C23 H21 N O4'
_chemical_formula_weight         375.42
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   13.0103(8)
_cell_length_b                   17.3840(11)
_cell_length_c                   17.8554(11)
_cell_angle_alpha                88.347(6)
_cell_angle_beta                 69.418(5)
_cell_angle_gamma                88.399(6)
_cell_volume                     3778.4(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    31385
_cell_measurement_theta_min      3.63
_cell_measurement_theta_max      68.67
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.300
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1584.00
_exptl_absorpt_coefficient_mu    0.736
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.556
_exptl_absorpt_correction_T_max  0.802

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      123
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            42483
_diffrn_reflns_av_unetI/netI     0.0737
_diffrn_reflns_av_R_equivalents  0.0752
_diffrn_reflns_theta_max         68.249
_diffrn_reflns_theta_min         3.630
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             13547
_reflns_number_gt                10548
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1409
_refine_ls_R_factor_gt           0.1191
_refine_ls_wR_factor_ref         0.3774
_refine_ls_wR_factor_gt          0.3659
_refine_ls_number_restraints     42
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         13547
_refine_ls_number_parameters     1037
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1773P)²+20.0224P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.83
_refine_diff_density_min         -0.64
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.6630(3) -0.3449(3) 0.8502(2) 0.0370(10) Uani 1 1 d . . . . .
O2 O 0.4824(4) -0.3636(3) 0.7009(3) 0.0494(12) Uani 1 1 d . . . . .
O3 O 0.7132(3) -0.1727(2) 0.7847(2) 0.0355(9) Uani 1 1 d . . . . .
O4 O 0.8676(3) -0.1326(2) 0.8001(2) 0.0350(9) Uani 1 1 d . . . . .
O5 O 0.1591(3) -0.1263(3) 1.1044(2) 0.0371(10) Uani 1 1 d . . . . .
O6 O -0.0359(3) -0.0889(3) 0.9658(3) 0.0431(11) Uani 1 1 d . . . . .
O7 O 0.1784(4) -0.3007(3) 1.0360(3) 0.0442(11) Uani 1 1 d . . . . .
O8 O 0.3317(4) -0.3652(3) 1.0318(3) 0.0507(12) Uani 1 1 d . . . . .
O9 O 0.3601(4) 0.3605(3) 0.6562(3) 0.0475(12) Uani 1 1 d . . . . .
O10 O 0.5117(4) 0.4044(3) 0.8200(3) 0.0590(14) Uani 1 1 d . . . . .
O11 O 0.3125(4) 0.1863(3) 0.7237(3) 0.0445(11) Uani 1 1 d . . . . .
O12 O 0.1642(4) 0.1402(3) 0.7063(3) 0.0473(12) Uani 1 1 d . . . . .
O13 O 1.0157(4) 0.0999(3) 0.5542(3) 0.0453(11) Uani 1 1 d . . . . .
O14 O 0.8460(3) 0.1627(2) 0.4025(2) 0.0356(9) Uani 1 1 d . . . . .
O15 O 0.8130(3) 0.3357(2) 0.4735(2) 0.0371(10) Uani 1 1 d . . . . .
O16 O 0.6582(4) 0.3967(2) 0.4728(3) 0.0495(12) Uani 1 1 d D . . . .
N1 N 0.6347(4) -0.3371(3) 0.7284(3) 0.0274(10) Uani 1 1 d . . . . .
N2 N 0.1206(4) -0.1262(3) 0.9856(3) 0.0262(9) Uani 1 1 d . . . . .
N3 N 0.3734(4) 0.3632(3) 0.7830(3) 0.0327(11) Uani 1 1 d . . . . .
N4 N 0.8725(4) 0.1520(3) 0.5250(3) 0.0263(10) Uani 1 1 d . . . . .
C1 C 0.5267(5) -0.3640(3) 0.7498(4) 0.0341(13) Uani 1 1 d . . . . .
C2 C 0.4742(5) -0.3947(4) 0.8335(4) 0.0438(16) Uani 1 1 d . . . . .
H2A H 0.524686 -0.389361 0.862798 0.053 Uiso 1 1 calc R U . . .
H2B H 0.406169 -0.365552 0.860369 0.053 Uiso 1 1 calc R U . . .
H2C H 0.457503 -0.449113 0.832188 0.053 Uiso 1 1 calc R U . . .
C3 C 0.6975(4) -0.3357(3) 0.7791(3) 0.0255(11) Uani 1 1 d . . . . .
C4 C 0.7024(4) -0.3165(3) 0.6485(3) 0.0264(11) Uani 1 1 d . . . . .
C5 C 0.6730(5) -0.3024(4) 0.5822(3) 0.0358(13) Uani 1 1 d . . . . .
H5 H 0.598828 -0.306265 0.585417 0.043 Uiso 1 1 calc R U . . .
C6 C 0.7551(6) -0.2825(4) 0.5105(4) 0.0409(15) Uani 1 1 d . . . . .
H6 H 0.737041 -0.273048 0.463858 0.049 Uiso 1 1 calc R U . . .
C7 C 0.8627(5) -0.2761(3) 0.5061(3) 0.0359(13) Uani 1 1 d . . . . .
H7 H 0.917845 -0.262981 0.456486 0.043 Uiso 1 1 calc R U . . .
C8 C 0.8912(5) -0.2887(3) 0.5734(3) 0.0295(12) Uani 1 1 d . . . . .
H8 H 0.965068 -0.283974 0.570449 0.035 Uiso 1 1 calc R U . . .
C9 C 0.8100(4) -0.3082(3) 0.6448(3) 0.0239(11) Uani 1 1 d . . . . .
C10 C 0.8164(4) -0.3220(3) 0.7268(3) 0.0244(11) Uani 1 1 d . . . . .
C11 C 0.8907(4) -0.3915(3) 0.7379(3) 0.0251(11) Uani 1 1 d . . . . .
H11 H 0.862480 -0.405541 0.796211 0.030 Uiso 1 1 calc R U . . .
C12 C 0.8876(5) -0.4639(3) 0.6942(3) 0.0284(12) Uani 1 1 d . . . . .
C13 C 0.8007(5) -0.5143(3) 0.7285(4) 0.0349(13) Uani 1 1 d . . . . .
H13 H 0.743119 -0.500120 0.776290 0.042 Uiso 1 1 calc R U . . .
C14 C 0.7966(5) -0.5835(3) 0.6953(5) 0.0427(15) Uani 1 1 d . . . . .
H14 H 0.737493 -0.617205 0.720302 0.051 Uiso 1 1 calc R U . . .
C15 C 0.8805(6) -0.6043(3) 0.6238(4) 0.0463(17) Uani 1 1 d . . . . .
H15 H 0.878550 -0.652090 0.599807 0.056 Uiso 1 1 calc R U . . .
C16 C 0.9656(7) -0.5547(4) 0.5889(4) 0.0485(17) Uani 1 1 d . . . . .
H16 H 1.022499 -0.568472 0.540622 0.058 Uiso 1 1 calc R U . . .
C17 C 0.9691(6) -0.4853(3) 0.6233(4) 0.0395(14) Uani 1 1 d . . . . .
H17 H 1.028149 -0.451629 0.598024 0.047 Uiso 1 1 calc R U . . .
C18 C 1.0025(5) -0.3546(3) 0.7210(3) 0.0304(12) Uani 1 1 d . . . . .
H18A H 1.043974 -0.381048 0.751640 0.036 Uiso 1 1 calc R U . . .
H18B H 1.047266 -0.355293 0.663265 0.036 Uiso 1 1 calc R U . . .
C19 C 0.9707(5) -0.2745(3) 0.7488(3) 0.0297(12) Uani 1 1 d . . . . .
H19 H 1.018042 -0.240354 0.761066 0.036 Uiso 1 1 calc R U . . .
C20 C 0.8690(4) -0.2564(3) 0.7544(3) 0.0246(11) Uani 1 1 d . . . . .
C21 C 0.8079(5) -0.1837(3) 0.7800(3) 0.0281(12) Uani 1 1 d . . . . .
C22 C 0.8133(5) -0.0607(3) 0.8329(4) 0.0388(14) Uani 1 1 d . . . . .
H22A H 0.855104 -0.036263 0.862318 0.047 Uiso 1 1 calc R U . . .
H22B H 0.738898 -0.071568 0.871411 0.047 Uiso 1 1 calc R U . . .
C23 C 0.8039(6) -0.0055(4) 0.7684(4) 0.0441(15) Uani 1 1 d . . . . .
H23A H 0.766825 0.042167 0.793027 0.053 Uiso 1 1 calc R U . . .
H23B H 0.877402 0.006257 0.730747 0.053 Uiso 1 1 calc R U . . .
H23C H 0.761225 -0.029040 0.739838 0.053 Uiso 1 1 calc R U . . .
C24 C 0.0109(4) -0.0992(3) 1.0130(3) 0.0301(12) Uani 1 1 d . . . . .
C25 C -0.0433(5) -0.0838(4) 1.0998(4) 0.0398(14) Uani 1 1 d . . . . .
H25A H 0.008193 -0.095792 1.127590 0.048 Uiso 1 1 calc R U . . .
H25B H -0.065911 -0.029489 1.106783 0.048 Uiso 1 1 calc R U . . .
H25C H -0.108082 -0.116128 1.122019 0.048 Uiso 1 1 calc R U . . .
C26 C 0.1828(4) -0.1451(3) 0.9048(3) 0.0262(11) Uani 1 1 d . . . . .
C27 C 0.1486(5) -0.1487(3) 0.8394(3) 0.0302(12) Uani 1 1 d . . . . .
H27 H 0.075290 -0.135767 0.843757 0.036 Uiso 1 1 calc R U . . .
C28 C 0.2270(5) -0.1721(3) 0.7672(3) 0.0335(13) Uani 1 1 d . . . . .
H28 H 0.206256 -0.174518 0.721300 0.040 Uiso 1 1 calc R U . . .
C29 C 0.3335(5) -0.1917(3) 0.7601(3) 0.0345(13) Uani 1 1 d . . . . .
H29 H 0.384282 -0.207808 0.710055 0.041 Uiso 1 1 calc R U . . .
C30 C 0.3671(5) -0.1881(3) 0.8259(3) 0.0297(12) Uani 1 1 d . . . . .
H30 H 0.440250 -0.201271 0.821638 0.036 Uiso 1 1 calc R U . . .
C31 C 0.2903(4) -0.1647(3) 0.8978(3) 0.0259(11) Uani 1 1 d . . . . .
C32 C 0.3031(4) -0.1590(3) 0.9785(3) 0.0278(12) Uani 1 1 d . . . . .
C33 C 0.3455(5) -0.2343(3) 1.0043(3) 0.0306(12) Uani 1 1 d . . . . .
C34 C 0.2761(5) -0.3020(3) 1.0256(3) 0.0364(14) Uani 1 1 d . . . . .
C35 C 0.2720(8) -0.4367(4) 1.0506(6) 0.079(3) Uani 1 1 d . . . . .
H35A H 0.221767 -0.436774 1.107097 0.094 Uiso 1 1 calc R U . . .
H35B H 0.227177 -0.441015 1.016230 0.094 Uiso 1 1 calc R U . . .
C36 C 0.3437(11) -0.4988(5) 1.0387(6) 0.113(5) Uani 1 1 d . . . . .
H36A H 0.302170 -0.546501 1.051662 0.136 Uiso 1 1 calc R U . . .
H36B H 0.392728 -0.499091 0.982637 0.136 Uiso 1 1 calc R U . . .
H36C H 0.387326 -0.494856 1.073362 0.136 Uiso 1 1 calc R U . . .
C37 C 0.4496(5) -0.2290(4) 0.9981(4) 0.0374(14) Uani 1 1 d . . . . .
H37 H 0.491092 -0.270402 1.009926 0.045 Uiso 1 1 calc R U . . .
C38 C 0.4945(5) -0.1513(3) 0.9707(4) 0.0355(13) Uani 1 1 d . . . . .
H38A H 0.541221 -0.151010 0.913317 0.043 Uiso 1 1 calc R U . . .
H38B H 0.537800 -0.133496 1.002416 0.043 Uiso 1 1 calc R U . . .
C39 C 0.3901(4) -0.1013(3) 0.9851(3) 0.0273(11) Uani 1 1 d . . . . .
H39 H 0.364898 -0.086360 1.042454 0.033 Uiso 1 1 calc R U . . .
C40 C 0.4000(4) -0.0269(3) 0.9370(3) 0.0276(11) Uani 1 1 d . . . . .
C41 C 0.3113(5) 0.0250(3) 0.9550(4) 0.0333(13) Uani 1 1 d . . . . .
H41 H 0.244285 0.011965 0.996137 0.040 Uiso 1 1 calc R U . . .
C42 C 0.3180(5) 0.0945(3) 0.9149(4) 0.0364(13) Uani 1 1 d . . . . .
H42 H 0.256268 0.128722 0.928166 0.044 Uiso 1 1 calc R U . . .
C43 C 0.4167(5) 0.1145(4) 0.8545(4) 0.0413(15) Uani 1 1 d . . . . .
H43 H 0.422768 0.162820 0.827119 0.050 Uiso 1 1 calc R U . . .
C44 C 0.5048(5) 0.0638(4) 0.8350(4) 0.0450(16) Uani 1 1 d . . . . .
H44 H 0.571569 0.076556 0.793402 0.054 Uiso 1 1 calc R U . . .
C45 C 0.4957(5) -0.0066(4) 0.8766(4) 0.0391(14) Uani 1 1 d . . . . .
H45 H 0.556938 -0.041248 0.862807 0.047 Uiso 1 1 calc R U . . .
C46 C 0.1875(4) -0.1364(3) 1.0328(3) 0.0281(11) Uani 1 1 d . . . . .
C47 C 0.3199(5) 0.3524(3) 0.7285(3) 0.0311(12) Uani 1 1 d . . . . .
C48 C 0.2013(4) 0.3340(3) 0.7746(3) 0.0249(11) Uani 1 1 d . . . . .
C49 C 0.2005(4) 0.3198(3) 0.8585(3) 0.0259(11) Uani 1 1 d . . . . .
C50 C 0.1195(5) 0.2915(3) 0.9252(3) 0.0301(12) Uani 1 1 d . . . . .
H50 H 0.049849 0.279264 0.923128 0.036 Uiso 1 1 calc R U . . .
C51 C 0.1409(6) 0.2811(3) 0.9962(4) 0.0390(14) Uani 1 1 d . . . . .
H51 H 0.085989 0.261180 1.042830 0.047 Uiso 1 1 calc R U . . .
C52 C 0.2436(6) 0.3000(4) 0.9982(4) 0.0453(16) Uani 1 1 d . . . . .
H52 H 0.257681 0.292910 1.046714 0.054 Uiso 1 1 calc R U . . .
C53 C 0.3247(6) 0.3287(4) 0.9315(4) 0.0398(14) Uani 1 1 d . . . . .
H53 H 0.394041 0.341610 0.933661 0.048 Uiso 1 1 calc R U . . .
C54 C 0.3031(5) 0.3385(3) 0.8612(3) 0.0313(12) Uani 1 1 d . . . . .
C55 C 0.4732(5) 0.4002(4) 0.7676(4) 0.0422(15) Uani 1 1 d . . . . .
C56 C 0.5274(5) 0.4351(4) 0.6859(5) 0.0488(17) Uani 1 1 d . . . . .
H56A H 0.483321 0.425301 0.652656 0.059 Uiso 1 1 calc R U . . .
H56B H 0.533474 0.490711 0.690199 0.059 Uiso 1 1 calc R U . . .
H56C H 0.600859 0.412026 0.661354 0.059 Uiso 1 1 calc R U . . .
C57 C 0.2181(5) 0.1946(3) 0.7236(3) 0.0346(13) Uani 1 1 d . . . . .
C58 C 0.2168(6) 0.0629(4) 0.6915(5) 0.0524(18) Uani 1 1 d . . . . .
H58A H 0.278651 0.062736 0.639650 0.063 Uiso 1 1 calc R U . . .
H58B H 0.245630 0.047944 0.734403 0.063 Uiso 1 1 calc R U . . .
C59 C 0.1338(7) 0.0097(4) 0.6903(5) 0.057(2) Uani 1 1 d . . . . .
H59A H 0.166022 -0.042371 0.680572 0.069 Uiso 1 1 calc R U . . .
H59B H 0.073223 0.010298 0.741876 0.069 Uiso 1 1 calc R U . . .
H59C H 0.106103 0.025026 0.647528 0.069 Uiso 1 1 calc R U . . .
C60 C 0.1553(5) 0.2673(3) 0.7444(3) 0.0294(12) Uani 1 1 d . . . . .
C61 C 0.0523(5) 0.2832(3) 0.7471(3) 0.0323(12) Uani 1 1 d . . . . .
H61 H 0.007873 0.247872 0.733171 0.039 Uiso 1 1 calc R U . . .
C62 C 0.0163(5) 0.3621(3) 0.7744(4) 0.0329(13) Uani 1 1 d . . . . .
H62A H -0.031958 0.361971 0.831405 0.039 Uiso 1 1 calc R U . . .
H62B H -0.023049 0.387546 0.741807 0.039 Uiso 1 1 calc R U . . .
C63 C 0.1248(5) 0.4019(3) 0.7623(3) 0.0282(12) Uani 1 1 d . . . . .
H63 H 0.155657 0.416600 0.704223 0.034 Uiso 1 1 calc R U . . .
C64 C 0.1223(5) 0.4745(3) 0.8071(3) 0.0314(12) Uani 1 1 d . . . . .
C65 C 0.0374(6) 0.4927(4) 0.8778(4) 0.0447(16) Uani 1 1 d . . . . .
H65 H -0.020768 0.457857 0.901013 0.054 Uiso 1 1 calc R U . . .
C66 C 0.0383(8) 0.5616(4) 0.9141(4) 0.056(2) Uani 1 1 d . . . . .
H66 H -0.019926 0.573145 0.962554 0.067 Uiso 1 1 calc R U . . .
C67 C 0.1188(7) 0.6134(4) 0.8834(4) 0.0489(18) Uani 1 1 d . . . . .
H67 H 0.116788 0.660638 0.909278 0.059 Uiso 1 1 calc R U . . .
C68 C 0.2045(6) 0.5960(4) 0.8132(5) 0.0471(17) Uani 1 1 d . . . . .
H68 H 0.262036 0.631441 0.790423 0.057 Uiso 1 1 calc R U . . .
C69 C 0.2059(5) 0.5273(3) 0.7768(4) 0.0361(13) Uani 1 1 d . . . . .
H69 H 0.265768 0.515473 0.729429 0.043 Uiso 1 1 calc R U . . .
C70 C 0.9763(5) 0.1143(3) 0.5037(4) 0.0318(12) Uani 1 1 d . . . . .
C71 C 1.0316(5) 0.0933(4) 0.4184(4) 0.0388(14) Uani 1 1 d . . . . .
H71A H 0.985581 0.110195 0.387588 0.047 Uiso 1 1 calc R U . . .
H71B H 1.102767 0.118451 0.396761 0.047 Uiso 1 1 calc R U . . .
H71C H 1.042768 0.037315 0.414809 0.047 Uiso 1 1 calc R U . . .
C72 C 0.8069(4) 0.1730(3) 0.6054(3) 0.0257(11) Uani 1 1 d . . . . .
C73 C 0.8373(5) 0.1759(3) 0.6722(3) 0.0317(12) Uani 1 1 d . . . . .
H73 H 0.908879 0.160336 0.670052 0.038 Uiso 1 1 calc R U . . .
C74 C 0.7591(5) 0.2024(3) 0.7426(3) 0.0334(13) Uani 1 1 d . . . . .
H74 H 0.777492 0.204315 0.789477 0.040 Uiso 1 1 calc R U . . .
C75 C 0.6555(5) 0.2260(3) 0.7459(3) 0.0348(13) Uani 1 1 d . . . . .
H75 H 0.604040 0.244411 0.794694 0.042 Uiso 1 1 calc R U . . .
C76 C 0.6256(5) 0.2231(3) 0.6779(3) 0.0302(12) Uani 1 1 d . . . . .
H76 H 0.554214 0.239003 0.679798 0.036 Uiso 1 1 calc R U . . .
C77 C 0.7030(4) 0.1965(3) 0.6078(3) 0.0261(11) Uani 1 1 d . . . . .
C78 C 0.6955(4) 0.1917(3) 0.5262(3) 0.0264(11) Uani 1 1 d . . . . .
C79 C 0.8117(4) 0.1685(3) 0.4747(3) 0.0262(11) Uani 1 1 d . . . . .
C80 C 0.6126(5) 0.1316(3) 0.5158(3) 0.0317(12) Uani 1 1 d . . . . .
H80 H 0.640117 0.118779 0.457759 0.038 Uiso 1 1 calc R U . . .
C81 C 0.6067(4) 0.0563(3) 0.5605(3) 0.0292(12) Uani 1 1 d . . . . .
C82 C 0.6872(5) -0.0005(4) 0.5288(4) 0.0395(14) Uani 1 1 d . . . . .
H82 H 0.745244 0.010186 0.479859 0.047 Uiso 1 1 calc R U . . .
C83 C 0.6856(6) -0.0712(4) 0.5656(4) 0.0453(16) Uani 1 1 d . . . . .
H83 H 0.741390 -0.108729 0.542481 0.054 Uiso 1 1 calc R U . . .
C84 C 0.5994(6) -0.0869(4) 0.6382(4) 0.0466(16) Uani 1 1 d . . . . .
H84 H 0.596055 -0.135535 0.664494 0.056 Uiso 1 1 calc R U . . .
C85 C 0.5215(7) -0.0319(4) 0.6703(4) 0.0531(18) Uani 1 1 d . . . . .
H85 H 0.463756 -0.042338 0.719533 0.064 Uiso 1 1 calc R U . . .
C86 C 0.5246(6) 0.0391(4) 0.6326(4) 0.0438(15) Uani 1 1 d . . . . .
H86 H 0.469374 0.076820 0.656596 0.053 Uiso 1 1 calc R U . . .
C87 C 0.5053(5) 0.1793(4) 0.5306(4) 0.0418(15) Uani 1 1 d . . . . .
H87A H 0.464026 0.161263 0.497457 0.050 Uiso 1 1 calc R U . . .
H87B H 0.457496 0.176955 0.587659 0.050 Uiso 1 1 calc R U . . .
C88 C 0.5466(5) 0.2587(4) 0.5059(4) 0.0368(13) Uani 1 1 d . . . . .
H88 H 0.503642 0.299787 0.495352 0.044 Uiso 1 1 calc R U . . .
C89 C 0.6501(5) 0.2651(3) 0.5004(3) 0.0289(12) Uani 1 1 d . . . . .
C90 C 0.7174(5) 0.3355(3) 0.4805(3) 0.0322(13) Uani 1 1 d . . . . .
C91A C 0.7100(19) 0.4686(9) 0.4378(11) 0.048(5) Uani 0.5 1 d D U P A 1
H91A H 0.664404 0.497847 0.412234 0.05(4) Uiso 0.5 1 calc R . P A 1
H91B H 0.783291 0.458538 0.396986 0.02(3) Uiso 0.5 1 calc R . P A 1
C92A C 0.7205(14) 0.5139(8) 0.5078(9) 0.063(5) Uani 0.5 1 d D U P A 1
H92A H 0.755278 0.563277 0.487555 0.06(5) Uiso 0.5 1 calc R . P A 1
H92B H 0.647397 0.523147 0.547670 0.06(5) Uiso 0.5 1 calc R . P A 1
H92C H 0.765638 0.484052 0.532505 0.03(3) Uiso 0.5 1 calc R . P A 1
C91B C 0.7183(16) 0.4680(8) 0.4669(12) 0.040(4) Uani 0.5 1 d D U P A 2
H91C H 0.776936 0.473346 0.413763 0.08(7) Uiso 0.5 1 calc R . P A 2
H91D H 0.751612 0.469184 0.508815 0.02(3) Uiso 0.5 1 calc R . P A 2
C92B C 0.6315(16) 0.5317(8) 0.4787(12) 0.077(6) Uani 0.5 1 d D U P A 2
H92D H 0.665613 0.581824 0.475581 0.14(9) Uiso 0.5 1 calc R . P A 2
H92E H 0.599164 0.529180 0.436937 0.17(13) Uiso 0.5 1 calc R . P A 2
H92F H 0.574007 0.525045 0.531360 0.06(4) Uiso 0.5 1 calc R . P A 2


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR2014 (Burla, et al., 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 1.196(6) . ?
O2 C1 1.202(7) . ?
O3 C21 1.215(7) . ?
O4 C21 1.332(6) . ?
O4 C22 1.451(7) . ?
O5 C46 1.216(6) . ?
O6 C24 1.209(7) . ?
O7 C34 1.218(8) . ?
O8 C34 1.322(8) . ?
O8 C35 1.452(9) . ?
O9 C47 1.217(7) . ?
O10 C55 1.212(8) . ?
O11 C57 1.233(8) . ?
O12 C57 1.299(7) . ?
O12 C58 1.479(8) . ?
O13 C70 1.202(7) . ?
O14 C79 1.212(6) . ?
O15 C90 1.206(7) . ?
O16 C90 1.329(7) . ?
O16 C91A 1.453(15) . ?
O16 C91B 1.465(14) . ?
N1 C1 1.411(7) . ?
N1 C3 1.418(7) . ?
N1 C4 1.429(7) . ?
N2 C24 1.407(7) . ?
N2 C46 1.413(7) . ?
N2 C26 1.427(7) . ?
N3 C55 1.400(8) . ?
N3 C47 1.400(7) . ?
N3 C54 1.436(8) . ?
N4 C79 1.411(7) . ?
N4 C70 1.415(7) . ?
N4 C72 1.440(7) . ?
C1 C2 1.497(9) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C10 1.522(7) . ?
C4 C5 1.381(8) . ?
C4 C9 1.389(7) . ?
C5 C6 1.391(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.382(9) . ?
C6 H6 0.9500 . ?
C7 C8 1.386(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.380(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.508(7) . ?
C10 C20 1.524(7) . ?
C10 C11 1.577(7) . ?
C11 C12 1.510(7) . ?
C11 C18 1.533(7) . ?
C11 H11 1.0000 . ?
C12 C17 1.388(9) . ?
C12 C13 1.400(8) . ?
C13 C14 1.366(9) . ?
C13 H13 0.9500 . ?
C14 C15 1.407(10) . ?
C14 H14 0.9500 . ?
C15 C16 1.376(10) . ?
C15 H15 0.9500 . ?
C16 C17 1.378(9) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.490(8) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.321(8) . ?
C19 H19 0.9500 . ?
C20 C21 1.470(8) . ?
C22 C23 1.513(9) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.488(8) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.392(7) . ?
C26 C31 1.392(8) . ?
C27 C28 1.398(8) . ?
C27 H27 0.9500 . ?
C28 C29 1.381(9) . ?
C28 H28 0.9500 . ?
C29 C30 1.394(8) . ?
C29 H29 0.9500 . ?
C30 C31 1.384(8) . ?
C30 H30 0.9500 . ?
C31 C32 1.514(7) . ?
C32 C46 1.523(8) . ?
C32 C33 1.528(8) . ?
C32 C39 1.569(7) . ?
C33 C37 1.325(8) . ?
C33 C34 1.463(8) . ?
C35 C36 1.377(14) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 C38 1.486(8) . ?
C37 H37 0.9500 . ?
C38 C39 1.539(8) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 C40 1.514(8) . ?
C39 H39 1.0000 . ?
C40 C45 1.377(8) . ?
C40 C41 1.396(8) . ?
C41 C42 1.375(8) . ?
C41 H41 0.9500 . ?
C42 C43 1.401(9) . ?
C42 H42 0.9500 . ?
C43 C44 1.375(9) . ?
C43 H43 0.9500 . ?
C44 C45 1.400(9) . ?
C44 H44 0.9500 . ?
C45 H45 0.9500 . ?
C47 C48 1.511(7) . ?
C48 C49 1.507(7) . ?
C48 C60 1.515(7) . ?
C48 C63 1.582(7) . ?
C49 C50 1.373(8) . ?
C49 C54 1.400(8) . ?
C50 C51 1.396(8) . ?
C50 H50 0.9500 . ?
C51 C52 1.398(10) . ?
C51 H51 0.9500 . ?
C52 C53 1.376(10) . ?
C52 H52 0.9500 . ?
C53 C54 1.384(8) . ?
C53 H53 0.9500 . ?
C55 C56 1.498(10) . ?
C56 H56A 0.9800 . ?
C56 H56B 0.9800 . ?
C56 H56C 0.9800 . ?
C57 C60 1.469(8) . ?
C58 C59 1.448(11) . ?
C58 H58A 0.9900 . ?
C58 H58B 0.9900 . ?
C59 H59A 0.9800 . ?
C59 H59B 0.9800 . ?
C59 H59C 0.9800 . ?
C60 C61 1.346(8) . ?
C61 C62 1.476(8) . ?
C61 H61 0.9500 . ?
C62 C63 1.532(8) . ?
C62 H62A 0.9900 . ?
C62 H62B 0.9900 . ?
C63 C64 1.508(8) . ?
C63 H63 1.0000 . ?
C64 C69 1.389(8) . ?
C64 C65 1.392(9) . ?
C65 C66 1.381(9) . ?
C65 H65 0.9500 . ?
C66 C67 1.352(11) . ?
C66 H66 0.9500 . ?
C67 C68 1.388(11) . ?
C67 H67 0.9500 . ?
C68 C69 1.372(9) . ?
C68 H68 0.9500 . ?
C69 H69 0.9500 . ?
C70 C71 1.488(8) . ?
C71 H71A 0.9800 . ?
C71 H71B 0.9800 . ?
C71 H71C 0.9800 . ?
C72 C73 1.385(7) . ?
C72 C77 1.388(8) . ?
C73 C74 1.391(8) . ?
C73 H73 0.9500 . ?
C74 C75 1.379(9) . ?
C74 H74 0.9500 . ?
C75 C76 1.403(8) . ?
C75 H75 0.9500 . ?
C76 C77 1.384(8) . ?
C76 H76 0.9500 . ?
C77 C78 1.499(7) . ?
C78 C89 1.518(8) . ?
C78 C79 1.518(8) . ?
C78 C80 1.582(7) . ?
C80 C81 1.502(8) . ?
C80 C87 1.548(9) . ?
C80 H80 1.0000 . ?
C81 C86 1.384(8) . ?
C81 C82 1.396(9) . ?
C82 C83 1.374(9) . ?
C82 H82 0.9500 . ?
C83 C84 1.410(10) . ?
C83 H83 0.9500 . ?
C84 C85 1.356(10) . ?
C84 H84 0.9500 . ?
C85 C86 1.385(9) . ?
C85 H85 0.9500 . ?
C86 H86 0.9500 . ?
C87 C88 1.492(9) . ?
C87 H87A 0.9900 . ?
C87 H87B 0.9900 . ?
C88 C89 1.323(8) . ?
C88 H88 0.9500 . ?
C89 C90 1.485(8) . ?
C91A C92A 1.544(16) . ?
C91A H91A 0.9900 . ?
C91A H91B 0.9900 . ?
C92A H92A 0.9800 . ?
C92A H92B 0.9800 . ?
C92A H92C 0.9800 . ?
C91B C92B 1.522(17) . ?
C91B H91C 0.9900 . ?
C91B H91D 0.9900 . ?
C92B H92D 0.9800 . ?
C92B H92E 0.9800 . ?
C92B H92F 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
C21 O4 C22 117.1(5) . . ?
C34 O8 C35 117.3(6) . . ?
C57 O12 C58 117.6(5) . . ?
C90 O16 C91A 121.2(10) . . ?
C90 O16 C91B 111.4(8) . . ?
C1 N1 C3 126.0(5) . . ?
C1 N1 C4 124.1(4) . . ?
C3 N1 C4 109.5(4) . . ?
C24 N2 C46 125.7(4) . . ?
C24 N2 C26 125.1(4) . . ?
C46 N2 C26 109.2(4) . . ?
C55 N3 C47 126.7(5) . . ?
C55 N3 C54 124.0(5) . . ?
C47 N3 C54 108.9(4) . . ?
C79 N4 C70 126.8(5) . . ?
C79 N4 C72 108.7(4) . . ?
C70 N4 C72 124.2(4) . . ?
O2 C1 N1 119.9(5) . . ?
O2 C1 C2 123.3(5) . . ?
N1 C1 C2 116.8(5) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O1 C3 N1 125.9(5) . . ?
O1 C3 C10 126.3(5) . . ?
N1 C3 C10 107.8(4) . . ?
C5 C4 C9 121.2(5) . . ?
C5 C4 N1 129.1(5) . . ?
C9 C4 N1 109.7(4) . . ?
C4 C5 C6 118.0(5) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C7 C6 C5 120.9(5) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 120.7(5) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 118.7(5) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C4 120.4(5) . . ?
C8 C9 C10 130.0(5) . . ?
C4 C9 C10 109.5(4) . . ?
C9 C10 C3 103.1(4) . . ?
C9 C10 C20 113.4(4) . . ?
C3 C10 C20 113.9(4) . . ?
C9 C10 C11 117.6(4) . . ?
C3 C10 C11 109.5(4) . . ?
C20 C10 C11 99.8(4) . . ?
C12 C11 C18 117.8(5) . . ?
C12 C11 C10 116.1(4) . . ?
C18 C11 C10 103.2(4) . . ?
C12 C11 H11 106.3 . . ?
C18 C11 H11 106.3 . . ?
C10 C11 H11 106.3 . . ?
C17 C12 C13 117.8(5) . . ?
C17 C12 C11 123.6(5) . . ?
C13 C12 C11 118.6(5) . . ?
C14 C13 C12 121.8(6) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C13 C14 C15 119.4(6) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C16 C15 C14 119.2(6) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C17 120.8(7) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C16 C17 C12 121.0(6) . . ?
C16 C17 H17 119.5 . . ?
C12 C17 H17 119.5 . . ?
C19 C18 C11 102.2(4) . . ?
C19 C18 H18A 111.3 . . ?
C11 C18 H18A 111.3 . . ?
C19 C18 H18B 111.3 . . ?
C11 C18 H18B 111.3 . . ?
H18A C18 H18B 109.2 . . ?
C20 C19 C18 112.2(5) . . ?
C20 C19 H19 123.9 . . ?
C18 C19 H19 123.9 . . ?
C19 C20 C21 128.5(5) . . ?
C19 C20 C10 111.2(5) . . ?
C21 C20 C10 120.3(5) . . ?
O3 C21 O4 124.3(5) . . ?
O3 C21 C20 123.9(5) . . ?
O4 C21 C20 111.8(5) . . ?
O4 C22 C23 112.1(5) . . ?
O4 C22 H22A 109.2 . . ?
C23 C22 H22A 109.2 . . ?
O4 C22 H22B 109.2 . . ?
C23 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O6 C24 N2 119.4(5) . . ?
O6 C24 C25 122.1(5) . . ?
N2 C24 C25 118.4(5) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 C31 120.9(5) . . ?
C27 C26 N2 129.1(5) . . ?
C31 C26 N2 109.9(4) . . ?
C26 C27 C28 116.9(5) . . ?
C26 C27 H27 121.5 . . ?
C28 C27 H27 121.5 . . ?
C29 C28 C27 122.2(5) . . ?
C29 C28 H28 118.9 . . ?
C27 C28 H28 118.9 . . ?
C28 C29 C30 120.5(5) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
C31 C30 C29 117.9(5) . . ?
C31 C30 H30 121.1 . . ?
C29 C30 H30 121.1 . . ?
C30 C31 C26 121.6(5) . . ?
C30 C31 C32 128.8(5) . . ?
C26 C31 C32 109.6(5) . . ?
C31 C32 C46 102.4(4) . . ?
C31 C32 C33 112.3(4) . . ?
C46 C32 C33 113.4(4) . . ?
C31 C32 C39 117.2(4) . . ?
C46 C32 C39 111.4(4) . . ?
C33 C32 C39 100.7(4) . . ?
C37 C33 C34 128.2(6) . . ?
C37 C33 C32 111.2(5) . . ?
C34 C33 C32 120.4(5) . . ?
O7 C34 O8 123.7(6) . . ?
O7 C34 C33 124.1(6) . . ?
O8 C34 C33 112.2(6) . . ?
C36 C35 O8 110.5(8) . . ?
C36 C35 H35A 109.5 . . ?
O8 C35 H35A 109.5 . . ?
C36 C35 H35B 109.5 . . ?
O8 C35 H35B 109.5 . . ?
H35A C35 H35B 108.1 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C33 C37 C38 112.7(5) . . ?
C33 C37 H37 123.7 . . ?
C38 C37 H37 123.7 . . ?
C37 C38 C39 102.7(5) . . ?
C37 C38 H38A 111.2 . . ?
C39 C38 H38A 111.2 . . ?
C37 C38 H38B 111.2 . . ?
C39 C38 H38B 111.2 . . ?
H38A C38 H38B 109.1 . . ?
C40 C39 C38 117.9(5) . . ?
C40 C39 C32 115.7(4) . . ?
C38 C39 C32 104.1(4) . . ?
C40 C39 H39 106.0 . . ?
C38 C39 H39 106.0 . . ?
C32 C39 H39 106.0 . . ?
C45 C40 C41 117.6(5) . . ?
C45 C40 C39 122.4(5) . . ?
C41 C40 C39 120.0(5) . . ?
C42 C41 C40 122.0(6) . . ?
C42 C41 H41 119.0 . . ?
C40 C41 H41 119.0 . . ?
C41 C42 C43 119.5(6) . . ?
C41 C42 H42 120.3 . . ?
C43 C42 H42 120.3 . . ?
C44 C43 C42 119.6(6) . . ?
C44 C43 H43 120.2 . . ?
C42 C43 H43 120.2 . . ?
C43 C44 C45 119.7(6) . . ?
C43 C44 H44 120.1 . . ?
C45 C44 H44 120.1 . . ?
C40 C45 C44 121.6(6) . . ?
C40 C45 H45 119.2 . . ?
C44 C45 H45 119.2 . . ?
O5 C46 N2 125.9(5) . . ?
O5 C46 C32 125.3(5) . . ?
N2 C46 C32 108.7(4) . . ?
O9 C47 N3 126.0(5) . . ?
O9 C47 C48 125.2(5) . . ?
N3 C47 C48 108.7(5) . . ?
C49 C48 C47 102.8(4) . . ?
C49 C48 C60 112.5(4) . . ?
C47 C48 C60 115.9(4) . . ?
C49 C48 C63 116.8(4) . . ?
C47 C48 C63 109.5(4) . . ?
C60 C48 C63 100.1(4) . . ?
C50 C49 C54 120.8(5) . . ?
C50 C49 C48 130.2(5) . . ?
C54 C49 C48 109.0(5) . . ?
C49 C50 C51 119.0(6) . . ?
C49 C50 H50 120.5 . . ?
C51 C50 H50 120.5 . . ?
C50 C51 C52 119.6(6) . . ?
C50 C51 H51 120.2 . . ?
C52 C51 H51 120.2 . . ?
C53 C52 C51 121.4(6) . . ?
C53 C52 H52 119.3 . . ?
C51 C52 H52 119.3 . . ?
C52 C53 C54 118.7(6) . . ?
C52 C53 H53 120.7 . . ?
C54 C53 H53 120.7 . . ?
C53 C54 C49 120.4(6) . . ?
C53 C54 N3 130.2(5) . . ?
C49 C54 N3 109.3(5) . . ?
O10 C55 N3 120.0(6) . . ?
O10 C55 C56 122.3(6) . . ?
N3 C55 C56 117.7(6) . . ?
C55 C56 H56A 109.5 . . ?
C55 C56 H56B 109.5 . . ?
H56A C56 H56B 109.5 . . ?
C55 C56 H56C 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
O11 C57 O12 123.7(6) . . ?
O11 C57 C60 122.7(5) . . ?
O12 C57 C60 113.6(6) . . ?
C59 C58 O12 107.3(6) . . ?
C59 C58 H58A 110.3 . . ?
O12 C58 H58A 110.3 . . ?
C59 C58 H58B 110.3 . . ?
O12 C58 H58B 110.3 . . ?
H58A C58 H58B 108.5 . . ?
C58 C59 H59A 109.5 . . ?
C58 C59 H59B 109.5 . . ?
H59A C59 H59B 109.5 . . ?
C58 C59 H59C 109.5 . . ?
H59A C59 H59C 109.5 . . ?
H59B C59 H59C 109.5 . . ?
C61 C60 C57 128.3(5) . . ?
C61 C60 C48 111.0(5) . . ?
C57 C60 C48 120.4(5) . . ?
C60 C61 C62 112.0(5) . . ?
C60 C61 H61 124.0 . . ?
C62 C61 H61 124.0 . . ?
C61 C62 C63 102.9(5) . . ?
C61 C62 H62A 111.2 . . ?
C63 C62 H62A 111.2 . . ?
C61 C62 H62B 111.2 . . ?
C63 C62 H62B 111.2 . . ?
H62A C62 H62B 109.1 . . ?
C64 C63 C62 118.7(5) . . ?
C64 C63 C48 116.2(4) . . ?
C62 C63 C48 103.3(4) . . ?
C64 C63 H63 105.9 . . ?
C62 C63 H63 105.9 . . ?
C48 C63 H63 105.9 . . ?
C69 C64 C65 117.5(6) . . ?
C69 C64 C63 119.8(6) . . ?
C65 C64 C63 122.7(5) . . ?
C66 C65 C64 119.7(7) . . ?
C66 C65 H65 120.2 . . ?
C64 C65 H65 120.2 . . ?
C67 C66 C65 122.5(7) . . ?
C67 C66 H66 118.8 . . ?
C65 C66 H66 118.8 . . ?
C66 C67 C68 118.7(6) . . ?
C66 C67 H67 120.7 . . ?
C68 C67 H67 120.7 . . ?
C69 C68 C67 119.7(6) . . ?
C69 C68 H68 120.2 . . ?
C67 C68 H68 120.2 . . ?
C68 C69 C64 122.0(6) . . ?
C68 C69 H69 119.0 . . ?
C64 C69 H69 119.0 . . ?
O13 C70 N4 119.5(5) . . ?
O13 C70 C71 122.8(5) . . ?
N4 C70 C71 117.7(5) . . ?
C70 C71 H71A 109.5 . . ?
C70 C71 H71B 109.5 . . ?
H71A C71 H71B 109.5 . . ?
C70 C71 H71C 109.5 . . ?
H71A C71 H71C 109.5 . . ?
H71B C71 H71C 109.5 . . ?
C73 C72 C77 121.6(5) . . ?
C73 C72 N4 128.9(5) . . ?
C77 C72 N4 109.4(4) . . ?
C72 C73 C74 117.5(5) . . ?
C72 C73 H73 121.3 . . ?
C74 C73 H73 121.3 . . ?
C75 C74 C73 121.6(5) . . ?
C75 C74 H74 119.2 . . ?
C73 C74 H74 119.2 . . ?
C74 C75 C76 120.5(5) . . ?
C74 C75 H75 119.8 . . ?
C76 C75 H75 119.8 . . ?
C77 C76 C75 118.1(5) . . ?
C77 C76 H76 121.0 . . ?
C75 C76 H76 121.0 . . ?
C76 C77 C72 120.7(5) . . ?
C76 C77 C78 129.2(5) . . ?
C72 C77 C78 110.0(5) . . ?
C77 C78 C89 112.8(4) . . ?
C77 C78 C79 102.7(4) . . ?
C89 C78 C79 115.8(4) . . ?
C77 C78 C80 116.9(4) . . ?
C89 C78 C80 99.9(4) . . ?
C79 C78 C80 109.3(4) . . ?
O14 C79 N4 125.5(5) . . ?
O14 C79 C78 125.9(5) . . ?
N4 C79 C78 108.6(4) . . ?
C81 C80 C87 118.5(5) . . ?
C81 C80 C78 115.6(4) . . ?
C87 C80 C78 103.8(5) . . ?
C81 C80 H80 106.0 . . ?
C87 C80 H80 106.0 . . ?
C78 C80 H80 106.0 . . ?
C86 C81 C82 117.0(6) . . ?
C86 C81 C80 123.6(5) . . ?
C82 C81 C80 119.4(5) . . ?
C83 C82 C81 122.5(6) . . ?
C83 C82 H82 118.7 . . ?
C81 C82 H82 118.7 . . ?
C82 C83 C84 118.7(6) . . ?
C82 C83 H83 120.7 . . ?
C84 C83 H83 120.7 . . ?
C85 C84 C83 119.5(6) . . ?
C85 C84 H84 120.3 . . ?
C83 C84 H84 120.3 . . ?
C84 C85 C86 121.0(7) . . ?
C84 C85 H85 119.5 . . ?
C86 C85 H85 119.5 . . ?
C81 C86 C85 121.3(6) . . ?
C81 C86 H86 119.4 . . ?
C85 C86 H86 119.4 . . ?
C88 C87 C80 102.6(5) . . ?
C88 C87 H87A 111.2 . . ?
C80 C87 H87A 111.2 . . ?
C88 C87 H87B 111.2 . . ?
C80 C87 H87B 111.2 . . ?
H87A C87 H87B 109.2 . . ?
C89 C88 C87 112.1(5) . . ?
C89 C88 H88 123.9 . . ?
C87 C88 H88 123.9 . . ?
C88 C89 C90 127.5(5) . . ?
C88 C89 C78 112.3(5) . . ?
C90 C89 C78 119.9(5) . . ?
O15 C90 O16 125.5(5) . . ?
O15 C90 C89 123.2(5) . . ?
O16 C90 C89 111.2(5) . . ?
O16 C91A C92A 105.9(11) . . ?
O16 C91A H91A 110.6 . . ?
C92A C91A H91A 110.6 . . ?
O16 C91A H91B 110.6 . . ?
C92A C91A H91B 110.6 . . ?
H91A C91A H91B 108.7 . . ?
C91A C92A H92A 109.5 . . ?
C91A C92A H92B 109.5 . . ?
H92A C92A H92B 109.5 . . ?
C91A C92A H92C 109.5 . . ?
H92A C92A H92C 109.5 . . ?
H92B C92A H92C 109.5 . . ?
O16 C91B C92B 104.4(13) . . ?
O16 C91B H91C 110.9 . . ?
C92B C91B H91C 110.9 . . ?
O16 C91B H91D 110.9 . . ?
C92B C91B H91D 110.9 . . ?
H91C C91B H91D 108.9 . . ?
C91B C92B H92D 109.5 . . ?
C91B C92B H92E 109.5 . . ?
H92D C92B H92E 109.5 . . ?
C91B C92B H92F 109.5 . . ?
H92D C92B H92F 109.5 . . ?
H92E C92B H92F 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 C1 O2 -178.7(6) . . . . ?
C4 N1 C1 O2 -7.4(9) . . . . ?
C3 N1 C1 C2 -0.7(8) . . . . ?
C4 N1 C1 C2 170.6(5) . . . . ?
C1 N1 C3 O1 -13.2(9) . . . . ?
C4 N1 C3 O1 174.4(5) . . . . ?
C1 N1 C3 C10 165.7(5) . . . . ?
C4 N1 C3 C10 -6.6(6) . . . . ?
C1 N1 C4 C5 15.3(9) . . . . ?
C3 N1 C4 C5 -172.2(6) . . . . ?
C1 N1 C4 C9 -167.5(5) . . . . ?
C3 N1 C4 C9 5.1(6) . . . . ?
C9 C4 C5 C6 2.4(9) . . . . ?
N1 C4 C5 C6 179.4(5) . . . . ?
C4 C5 C6 C7 -0.7(9) . . . . ?
C5 C6 C7 C8 -0.7(9) . . . . ?
C6 C7 C8 C9 0.4(8) . . . . ?
C7 C8 C9 C4 1.3(8) . . . . ?
C7 C8 C9 C10 -177.4(5) . . . . ?
C5 C4 C9 C8 -2.8(8) . . . . ?
N1 C4 C9 C8 179.7(5) . . . . ?
C5 C4 C9 C10 176.2(5) . . . . ?
N1 C4 C9 C10 -1.3(6) . . . . ?
C8 C9 C10 C3 176.3(5) . . . . ?
C4 C9 C10 C3 -2.6(5) . . . . ?
C8 C9 C10 C20 52.6(7) . . . . ?
C4 C9 C10 C20 -126.2(5) . . . . ?
C8 C9 C10 C11 -63.1(7) . . . . ?
C4 C9 C10 C11 118.0(5) . . . . ?
O1 C3 C10 C9 -175.5(5) . . . . ?
N1 C3 C10 C9 5.5(5) . . . . ?
O1 C3 C10 C20 -52.3(7) . . . . ?
N1 C3 C10 C20 128.8(5) . . . . ?
O1 C3 C10 C11 58.5(7) . . . . ?
N1 C3 C10 C11 -120.4(4) . . . . ?
C9 C10 C11 C12 -39.3(6) . . . . ?
C3 C10 C11 C12 77.9(5) . . . . ?
C20 C10 C11 C12 -162.3(4) . . . . ?
C9 C10 C11 C18 91.2(5) . . . . ?
C3 C10 C11 C18 -151.7(4) . . . . ?
C20 C10 C11 C18 -31.8(5) . . . . ?
C18 C11 C12 C17 -21.4(8) . . . . ?
C10 C11 C12 C17 101.7(6) . . . . ?
C18 C11 C12 C13 155.4(5) . . . . ?
C10 C11 C12 C13 -81.5(6) . . . . ?
C17 C12 C13 C14 1.7(8) . . . . ?
C11 C12 C13 C14 -175.3(5) . . . . ?
C12 C13 C14 C15 -1.2(9) . . . . ?
C13 C14 C15 C16 0.3(9) . . . . ?
C14 C15 C16 C17 0.0(10) . . . . ?
C15 C16 C17 C12 0.6(10) . . . . ?
C13 C12 C17 C16 -1.4(9) . . . . ?
C11 C12 C17 C16 175.5(6) . . . . ?
C12 C11 C18 C19 160.4(4) . . . . ?
C10 C11 C18 C19 31.0(5) . . . . ?
C11 C18 C19 C20 -18.7(6) . . . . ?
C18 C19 C20 C21 179.5(5) . . . . ?
C18 C19 C20 C10 -2.7(6) . . . . ?
C9 C10 C20 C19 -103.9(5) . . . . ?
C3 C10 C20 C19 138.6(5) . . . . ?
C11 C10 C20 C19 22.0(5) . . . . ?
C9 C10 C20 C21 74.1(6) . . . . ?
C3 C10 C20 C21 -43.3(6) . . . . ?
C11 C10 C20 C21 -159.9(4) . . . . ?
C22 O4 C21 O3 2.6(8) . . . . ?
C22 O4 C21 C20 -175.0(5) . . . . ?
C19 C20 C21 O3 -178.5(5) . . . . ?
C10 C20 C21 O3 3.8(8) . . . . ?
C19 C20 C21 O4 -0.9(8) . . . . ?
C10 C20 C21 O4 -178.6(4) . . . . ?
C21 O4 C22 C23 -78.4(7) . . . . ?
C46 N2 C24 O6 175.9(5) . . . . ?
C26 N2 C24 O6 -1.8(8) . . . . ?
C46 N2 C24 C25 -3.7(8) . . . . ?
C26 N2 C24 C25 178.6(5) . . . . ?
C24 N2 C26 C27 -6.9(8) . . . . ?
C46 N2 C26 C27 175.0(5) . . . . ?
C24 N2 C26 C31 175.8(5) . . . . ?
C46 N2 C26 C31 -2.3(6) . . . . ?
C31 C26 C27 C28 -0.4(8) . . . . ?
N2 C26 C27 C28 -177.5(5) . . . . ?
C26 C27 C28 C29 0.6(8) . . . . ?
C27 C28 C29 C30 -0.6(9) . . . . ?
C28 C29 C30 C31 0.3(8) . . . . ?
C29 C30 C31 C26 0.0(8) . . . . ?
C29 C30 C31 C32 177.1(5) . . . . ?
C27 C26 C31 C30 0.1(8) . . . . ?
N2 C26 C31 C30 177.7(5) . . . . ?
C27 C26 C31 C32 -177.5(5) . . . . ?
N2 C26 C31 C32 0.1(6) . . . . ?
C30 C31 C32 C46 -175.5(5) . . . . ?
C26 C31 C32 C46 1.9(6) . . . . ?
C30 C31 C32 C33 -53.5(7) . . . . ?
C26 C31 C32 C33 123.9(5) . . . . ?
C30 C31 C32 C39 62.3(8) . . . . ?
C26 C31 C32 C39 -120.3(5) . . . . ?
C31 C32 C33 C37 106.3(6) . . . . ?
C46 C32 C33 C37 -138.2(5) . . . . ?
C39 C32 C33 C37 -19.1(6) . . . . ?
C31 C32 C33 C34 -68.9(6) . . . . ?
C46 C32 C33 C34 46.5(7) . . . . ?
C39 C32 C33 C34 165.6(5) . . . . ?
C35 O8 C34 O7 1.3(9) . . . . ?
C35 O8 C34 C33 -178.4(6) . . . . ?
C37 C33 C34 O7 174.1(6) . . . . ?
C32 C33 C34 O7 -11.5(9) . . . . ?
C37 C33 C34 O8 -6.2(9) . . . . ?
C32 C33 C34 O8 168.2(5) . . . . ?
C34 O8 C35 C36 167.4(8) . . . . ?
C34 C33 C37 C38 176.7(5) . . . . ?
C32 C33 C37 C38 1.9(7) . . . . ?
C33 C37 C38 C39 16.6(7) . . . . ?
C37 C38 C39 C40 -157.1(5) . . . . ?
C37 C38 C39 C32 -27.3(5) . . . . ?
C31 C32 C39 C40 36.9(7) . . . . ?
C46 C32 C39 C40 -80.5(6) . . . . ?
C33 C32 C39 C40 159.0(5) . . . . ?
C31 C32 C39 C38 -94.2(5) . . . . ?
C46 C32 C39 C38 148.4(5) . . . . ?
C33 C32 C39 C38 27.9(5) . . . . ?
C38 C39 C40 C45 6.2(8) . . . . ?
C32 C39 C40 C45 -118.0(6) . . . . ?
C38 C39 C40 C41 -171.8(5) . . . . ?
C32 C39 C40 C41 64.0(7) . . . . ?
C45 C40 C41 C42 -0.6(8) . . . . ?
C39 C40 C41 C42 177.5(5) . . . . ?
C40 C41 C42 C43 -0.4(9) . . . . ?
C41 C42 C43 C44 1.2(9) . . . . ?
C42 C43 C44 C45 -1.1(10) . . . . ?
C41 C40 C45 C44 0.7(9) . . . . ?
C39 C40 C45 C44 -177.4(6) . . . . ?
C43 C44 C45 C40 0.1(11) . . . . ?
C24 N2 C46 O5 3.1(9) . . . . ?
C26 N2 C46 O5 -178.9(5) . . . . ?
C24 N2 C46 C32 -174.5(5) . . . . ?
C26 N2 C46 C32 3.5(6) . . . . ?
C31 C32 C46 O5 179.1(5) . . . . ?
C33 C32 C46 O5 57.9(7) . . . . ?
C39 C32 C46 O5 -54.8(7) . . . . ?
C31 C32 C46 N2 -3.3(5) . . . . ?
C33 C32 C46 N2 -124.5(5) . . . . ?
C39 C32 C46 N2 122.8(5) . . . . ?
C55 N3 C47 O9 14.4(10) . . . . ?
C54 N3 C47 O9 -172.7(6) . . . . ?
C55 N3 C47 C48 -161.8(5) . . . . ?
C54 N3 C47 C48 11.1(6) . . . . ?
O9 C47 C48 C49 172.6(6) . . . . ?
N3 C47 C48 C49 -11.1(6) . . . . ?
O9 C47 C48 C60 49.5(8) . . . . ?
N3 C47 C48 C60 -134.2(5) . . . . ?
O9 C47 C48 C63 -62.7(7) . . . . ?
N3 C47 C48 C63 113.6(5) . . . . ?
C47 C48 C49 C50 -170.9(5) . . . . ?
C60 C48 C49 C50 -45.6(8) . . . . ?
C63 C48 C49 C50 69.3(7) . . . . ?
C47 C48 C49 C54 7.2(6) . . . . ?
C60 C48 C49 C54 132.6(5) . . . . ?
C63 C48 C49 C54 -112.5(5) . . . . ?
C54 C49 C50 C51 -0.4(8) . . . . ?
C48 C49 C50 C51 177.6(5) . . . . ?
C49 C50 C51 C52 0.5(8) . . . . ?
C50 C51 C52 C53 -0.2(9) . . . . ?
C51 C52 C53 C54 -0.3(9) . . . . ?
C52 C53 C54 C49 0.4(9) . . . . ?
C52 C53 C54 N3 -176.5(6) . . . . ?
C50 C49 C54 C53 -0.1(8) . . . . ?
C48 C49 C54 C53 -178.4(5) . . . . ?
C50 C49 C54 N3 177.4(5) . . . . ?
C48 C49 C54 N3 -1.0(6) . . . . ?
C55 N3 C54 C53 -16.1(9) . . . . ?
C47 N3 C54 C53 170.7(6) . . . . ?
C55 N3 C54 C49 166.8(5) . . . . ?
C47 N3 C54 C49 -6.4(6) . . . . ?
C47 N3 C55 O10 -178.6(6) . . . . ?
C54 N3 C55 O10 9.5(9) . . . . ?
C47 N3 C55 C56 2.7(9) . . . . ?
C54 N3 C55 C56 -169.2(5) . . . . ?
C58 O12 C57 O11 4.5(9) . . . . ?
C58 O12 C57 C60 -174.8(5) . . . . ?
C57 O12 C58 C59 168.2(6) . . . . ?
O11 C57 C60 C61 -179.4(6) . . . . ?
O12 C57 C60 C61 -0.1(9) . . . . ?
O11 C57 C60 C48 -5.7(8) . . . . ?
O12 C57 C60 C48 173.5(5) . . . . ?
C49 C48 C60 C61 102.8(5) . . . . ?
C47 C48 C60 C61 -139.3(5) . . . . ?
C63 C48 C60 C61 -21.8(6) . . . . ?
C49 C48 C60 C57 -71.8(6) . . . . ?
C47 C48 C60 C57 46.0(7) . . . . ?
C63 C48 C60 C57 163.5(5) . . . . ?
C57 C60 C61 C62 177.3(5) . . . . ?
C48 C60 C61 C62 3.1(7) . . . . ?
C60 C61 C62 C63 17.9(6) . . . . ?
C61 C62 C63 C64 -160.4(5) . . . . ?
C61 C62 C63 C48 -30.1(5) . . . . ?
C49 C48 C63 C64 41.3(7) . . . . ?
C47 C48 C63 C64 -74.8(6) . . . . ?
C60 C48 C63 C64 162.9(5) . . . . ?
C49 C48 C63 C62 -90.5(5) . . . . ?
C47 C48 C63 C62 153.4(4) . . . . ?
C60 C48 C63 C62 31.1(5) . . . . ?
C62 C63 C64 C69 -154.9(5) . . . . ?
C48 C63 C64 C69 80.9(6) . . . . ?
C62 C63 C64 C65 23.5(8) . . . . ?
C48 C63 C64 C65 -100.6(7) . . . . ?
C69 C64 C65 C66 0.9(9) . . . . ?
C63 C64 C65 C66 -177.6(6) . . . . ?
C64 C65 C66 C67 0.4(11) . . . . ?
C65 C66 C67 C68 -0.8(11) . . . . ?
C66 C67 C68 C69 0.0(10) . . . . ?
C67 C68 C69 C64 1.4(9) . . . . ?
C65 C64 C69 C68 -1.8(9) . . . . ?
C63 C64 C69 C68 176.7(5) . . . . ?
C79 N4 C70 O13 -175.6(5) . . . . ?
C72 N4 C70 O13 -2.0(8) . . . . ?
C79 N4 C70 C71 3.7(8) . . . . ?
C72 N4 C70 C71 177.3(5) . . . . ?
C79 N4 C72 C73 -171.3(5) . . . . ?
C70 N4 C72 C73 14.2(8) . . . . ?
C79 N4 C72 C77 4.9(6) . . . . ?
C70 N4 C72 C77 -169.7(5) . . . . ?
C77 C72 C73 C74 0.8(8) . . . . ?
N4 C72 C73 C74 176.5(5) . . . . ?
C72 C73 C74 C75 -0.8(8) . . . . ?
C73 C74 C75 C76 0.7(8) . . . . ?
C74 C75 C76 C77 -0.4(8) . . . . ?
C75 C76 C77 C72 0.3(8) . . . . ?
C75 C76 C77 C78 -176.1(5) . . . . ?
C73 C72 C77 C76 -0.6(8) . . . . ?
N4 C72 C77 C76 -177.0(5) . . . . ?
C73 C72 C77 C78 176.5(5) . . . . ?
N4 C72 C77 C78 0.1(6) . . . . ?
C76 C77 C78 C89 46.9(7) . . . . ?
C72 C77 C78 C89 -129.9(5) . . . . ?
C76 C77 C78 C79 172.3(5) . . . . ?
C72 C77 C78 C79 -4.5(5) . . . . ?
C76 C77 C78 C80 -68.1(7) . . . . ?
C72 C77 C78 C80 115.1(5) . . . . ?
C70 N4 C79 O14 -11.1(9) . . . . ?
C72 N4 C79 O14 174.5(5) . . . . ?
C70 N4 C79 C78 166.6(5) . . . . ?
C72 N4 C79 C78 -7.7(6) . . . . ?
C77 C78 C79 O14 -174.9(5) . . . . ?
C89 C78 C79 O14 -51.5(7) . . . . ?
C80 C78 C79 O14 60.4(7) . . . . ?
C77 C78 C79 N4 7.4(5) . . . . ?
C89 C78 C79 N4 130.8(5) . . . . ?
C80 C78 C79 N4 -117.3(5) . . . . ?
C77 C78 C80 C81 -38.5(7) . . . . ?
C89 C78 C80 C81 -160.6(5) . . . . ?
C79 C78 C80 C81 77.4(6) . . . . ?
C77 C78 C80 C87 93.0(6) . . . . ?
C89 C78 C80 C87 -29.1(5) . . . . ?
C79 C78 C80 C87 -151.1(5) . . . . ?
C87 C80 C81 C86 -24.1(8) . . . . ?
C78 C80 C81 C86 100.0(7) . . . . ?
C87 C80 C81 C82 155.7(5) . . . . ?
C78 C80 C81 C82 -80.2(7) . . . . ?
C86 C81 C82 C83 1.2(9) . . . . ?
C80 C81 C82 C83 -178.6(6) . . . . ?
C81 C82 C83 C84 -0.1(10) . . . . ?
C82 C83 C84 C85 -0.7(10) . . . . ?
C83 C84 C85 C86 0.5(11) . . . . ?
C82 C81 C86 C85 -1.4(9) . . . . ?
C80 C81 C86 C85 178.4(6) . . . . ?
C84 C85 C86 C81 0.6(11) . . . . ?
C81 C80 C87 C88 157.5(5) . . . . ?
C78 C80 C87 C88 27.7(6) . . . . ?
C80 C87 C88 C89 -15.8(7) . . . . ?
C87 C88 C89 C90 -177.6(5) . . . . ?
C87 C88 C89 C78 -3.9(7) . . . . ?
C77 C78 C89 C88 -103.7(6) . . . . ?
C79 C78 C89 C88 138.3(5) . . . . ?
C80 C78 C89 C88 21.1(6) . . . . ?
C77 C78 C89 C90 70.5(6) . . . . ?
C79 C78 C89 C90 -47.4(7) . . . . ?
C80 C78 C89 C90 -164.6(5) . . . . ?
C91A O16 C90 O15 13.6(12) . . . . ?
C91B O16 C90 O15 -8.9(11) . . . . ?
C91A O16 C90 C89 -167.4(9) . . . . ?
C91B O16 C90 C89 170.2(10) . . . . ?
C88 C89 C90 O15 -176.9(6) . . . . ?
C78 C89 C90 O15 9.8(8) . . . . ?
C88 C89 C90 O16 4.0(8) . . . . ?
C78 C89 C90 O16 -169.3(5) . . . . ?
C90 O16 C91A C92A -88.2(16) . . . . ?
C90 O16 C91B C92B -166.8(11) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


