# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_ns420JL923c
_database_code_depnum_ccdc_archive 'CCDC 2291928'
loop_
_audit_author_name
_audit_author_address
'Noriyuki Suzuki'
;Sophia University
Japan
;
_audit_update_record             
;
2023-08-31 deposited with the CCDC.	2023-11-09 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C36 H24 N2 O4'
_chemical_formula_moiety         'C36 H24 N2 O4'
_chemical_formula_weight         548.60
_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                   7.5025(4)
_cell_length_b                   13.4118(6)
_cell_length_c                   14.2343(5)
_cell_angle_alpha                103.527(4)
_cell_angle_beta                 104.171(4)
_cell_angle_gamma                101.131(4)
_cell_volume                     1301.70(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4676
_cell_measurement_theta_min      3.34
_cell_measurement_theta_max      75.99
_cell_measurement_temperature    153
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            clearlightbrown
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             572.00
_exptl_absorpt_coefficient_mu    0.741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.544
_exptl_absorpt_correction_T_max  0.993

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

_diffrn_ambient_temperature      153
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            14514
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_theta_max         68.240
_diffrn_reflns_theta_min         3.352
_diffrn_reflns_theta_full        68.240
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4689
_reflns_number_gt                3784
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# 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          0.0728
_refine_ls_R_factor_gt           0.0555
_refine_ls_wR_factor_ref         0.1502
_refine_ls_wR_factor_gt          0.1409
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4689
_refine_ls_number_parameters     380
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0759P)²+0.3327P] 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         0.50
_refine_diff_density_min         -0.24
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1984(2) 0.67156(11) 0.27577(12) 0.0309(4) Uani 1 1 d . . .
O2 O 0.4055(2) 0.77169(12) 0.45738(12) 0.0363(4) Uani 1 1 d . . .
O3 O 0.3576(2) 0.48072(11) 0.20711(11) 0.0285(3) Uani 1 1 d . . .
O4 O 0.2208(2) 0.26332(11) -0.07345(12) 0.0323(4) Uani 1 1 d . . .
N1 N 0.1756(3) 0.62333(14) -0.13095(14) 0.0285(4) Uani 1 1 d . . .
N2 N 0.2782(3) 0.76407(13) 0.06154(13) 0.0270(4) Uani 1 1 d . . .
C1 C 0.1427(3) 0.72414(16) -0.12095(17) 0.0265(5) Uani 1 1 d . . .
C2 C 0.0590(3) 0.75496(18) -0.20430(18) 0.0307(5) Uani 1 1 d . . .
H2 H 0.0137 0.7052 -0.2701 0.037 Uiso 1 1 calc R . .
C3 C 0.0412(3) 0.85817(19) -0.19187(19) 0.0355(5) Uani 1 1 d . . .
H3 H -0.0151 0.8786 -0.2493 0.043 Uiso 1 1 calc R . .
C4 C 0.1043(4) 0.93089(19) -0.09719(19) 0.0360(5) Uani 1 1 d . . .
H4 H 0.0947 1.0018 -0.0892 0.043 Uiso 1 1 calc R . .
C5 C 0.1827(3) 0.89981(17) -0.01299(18) 0.0316(5) Uani 1 1 d . . .
H5 H 0.2249 0.9497 0.0527 0.038 Uiso 1 1 calc R . .
C6 C 0.1998(3) 0.79691(16) -0.02377(17) 0.0261(5) Uani 1 1 d . . .
C7 C 0.1419(4) 0.55162(18) -0.23128(17) 0.0324(5) Uani 1 1 d . . .
H7A H 0.2281 0.5053 -0.2272 0.039 Uiso 1 1 calc R . .
H7B H 0.1655 0.5932 -0.2773 0.039 Uiso 1 1 calc R . .
H7C H 0.0095 0.5080 -0.2570 0.039 Uiso 1 1 calc R . .
C8 C 0.3536(3) 0.84447(15) 0.15876(16) 0.0264(5) Uani 1 1 d . . .
C9 C 0.5464(3) 0.89628(17) 0.19328(17) 0.0298(5) Uani 1 1 d . . .
H9 H 0.6271 0.8796 0.1532 0.036 Uiso 1 1 calc R . .
C10 C 0.6198(4) 0.97287(17) 0.28730(18) 0.0344(5) Uani 1 1 d . . .
H10 H 0.7520 1.0083 0.3121 0.041 Uiso 1 1 calc R . .
C11 C 0.5018(4) 0.99807(17) 0.34524(18) 0.0370(6) Uani 1 1 d . . .
H11 H 0.5533 1.0494 0.4102 0.044 Uiso 1 1 calc R . .
C12 C 0.3082(4) 0.94800(17) 0.30783(19) 0.0368(6) Uani 1 1 d . . .
H12 H 0.2269 0.9661 0.3470 0.044 Uiso 1 1 calc R . .
C13 C 0.2321(3) 0.87164(17) 0.21379(18) 0.0321(5) Uani 1 1 d . . .
H13 H 0.0989 0.8385 0.1876 0.038 Uiso 1 1 calc R . .
C14 C 0.2134(3) 0.58457(16) -0.04695(16) 0.0240(4) Uani 1 1 d . . .
C15 C 0.2691(3) 0.65752(16) 0.05335(16) 0.0234(4) Uani 1 1 d . . .
C16 C 0.3111(3) 0.61847(16) 0.13661(16) 0.0249(4) Uani 1 1 d . . .
C17 C 0.3093(3) 0.51029(16) 0.12005(16) 0.0246(4) Uani 1 1 d . . .
C18 C 0.2592(3) 0.43970(16) 0.02423(16) 0.0247(4) Uani 1 1 d . . .
C19 C 0.2057(3) 0.47887(16) -0.05881(16) 0.0249(4) Uani 1 1 d . . .
H19 H 0.1626 0.4307 -0.1254 0.030 Uiso 1 1 calc R . .
C20 C 0.3418(3) 0.67585(15) 0.24682(16) 0.0233(4) Uani 1 1 d . . .
C21 C 0.5333(3) 0.72490(15) 0.31828(16) 0.0245(4) Uani 1 1 d . . .
C22 C 0.5574(3) 0.77301(16) 0.42121(16) 0.0280(5) Uani 1 1 d . . .
C23 C 0.7381(4) 0.82337(18) 0.48821(18) 0.0366(5) Uani 1 1 d . . .
H23 H 0.7542 0.8550 0.5579 0.044 Uiso 1 1 calc R . .
C24 C 0.8953(4) 0.82739(19) 0.4533(2) 0.0418(6) Uani 1 1 d . . .
H24 H 1.0188 0.8639 0.4991 0.050 Uiso 1 1 calc R . .
C25 C 0.8749(3) 0.77884(19) 0.35242(19) 0.0371(6) Uani 1 1 d . . .
H25 H 0.9839 0.7806 0.3295 0.044 Uiso 1 1 calc R . .
C26 C 0.6953(3) 0.72805(17) 0.28586(17) 0.0287(5) Uani 1 1 d . . .
H26 H 0.6812 0.6946 0.2168 0.034 Uiso 1 1 calc R . .
C27 C 0.2671(3) 0.32980(16) 0.01076(16) 0.0258(5) Uani 1 1 d . . .
C28 C 0.3385(3) 0.30409(16) 0.10558(17) 0.0265(5) Uani 1 1 d . . .
C29 C 0.3766(3) 0.37956(16) 0.19898(17) 0.0266(5) Uani 1 1 d . . .
C30 C 0.4393(3) 0.35700(18) 0.29004(18) 0.0315(5) Uani 1 1 d . . .
H30 H 0.4604 0.4085 0.3529 0.038 Uiso 1 1 calc R . .
C31 C 0.4704(3) 0.25823(18) 0.28740(19) 0.0359(5) Uani 1 1 d . . .
H31 H 0.5139 0.2418 0.3490 0.043 Uiso 1 1 calc R . .
C32 C 0.4384(4) 0.18275(18) 0.19516(19) 0.0360(5) Uani 1 1 d . . .
H32 H 0.4624 0.1156 0.1941 0.043 Uiso 1 1 calc R . .
C33 C 0.3725(3) 0.20500(17) 0.10575(18) 0.0307(5) Uani 1 1 d . . .
H33 H 0.3495 0.1526 0.0432 0.037 Uiso 1 1 calc R . .
C34 C -0.0552(4) 0.3968(2) 0.5020(2) 0.0464(7) Uani 1 1 d . . .
H34 H -0.0936 0.3255 0.5032 0.056 Uiso 1 1 calc R . .
C35 C 0.1176(4) 0.4332(2) 0.4877(2) 0.0451(6) Uani 1 1 d . . .
H35 H 0.1983 0.3874 0.4794 0.054 Uiso 1 1 calc R . .
C36 C 0.1734(4) 0.5376(2) 0.48542(19) 0.0429(6) Uani 1 1 d . . .
H36 H 0.2922 0.5634 0.4753 0.051 Uiso 1 1 calc R . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (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 C20 1.239(3) . ?
O2 C22 1.359(3) . ?
O3 C29 1.373(2) . ?
O3 C17 1.375(3) . ?
O4 C27 1.237(3) . ?
N1 C14 1.401(3) . ?
N1 C1 1.402(3) . ?
N1 C7 1.455(3) . ?
N2 C15 1.393(3) . ?
N2 C6 1.419(3) . ?
N2 C8 1.443(3) . ?
C1 C2 1.392(3) . ?
C1 C6 1.402(3) . ?
C2 C3 1.391(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.373(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(3) . ?
C5 H5 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.386(3) . ?
C8 C13 1.387(3) . ?
C9 C10 1.388(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C19 1.376(3) . ?
C14 C15 1.438(3) . ?
C15 C16 1.396(3) . ?
C16 C17 1.411(3) . ?
C16 C20 1.515(3) . ?
C17 C18 1.380(3) . ?
C18 C19 1.405(3) . ?
C18 C27 1.456(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.462(3) . ?
C21 C26 1.399(3) . ?
C21 C22 1.407(3) . ?
C22 C23 1.384(3) . ?
C23 C24 1.384(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.388(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.377(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.471(3) . ?
C28 C29 1.395(3) . ?
C28 C33 1.401(3) . ?
C29 C30 1.390(3) . ?
C30 C31 1.382(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.392(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.371(3) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C34 C35 1.376(4) . ?
C34 C36 1.378(4) 2_566 ?
C34 H34 0.9500 . ?
C35 C36 1.392(4) . ?
C35 H35 0.9500 . ?
C36 C34 1.378(4) 2_566 ?
C36 H36 0.9500 . ?

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
C29 O3 C17 118.54(16) . . ?
C14 N1 C1 120.63(17) . . ?
C14 N1 C7 118.86(17) . . ?
C1 N1 C7 119.85(18) . . ?
C15 N2 C6 121.56(17) . . ?
C15 N2 C8 121.14(17) . . ?
C6 N2 C8 117.10(16) . . ?
C2 C1 N1 122.2(2) . . ?
C2 C1 C6 119.08(19) . . ?
N1 C1 C6 118.69(19) . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.4(2) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.8(2) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 119.6(2) . . ?
C5 C6 N2 121.37(19) . . ?
C1 C6 N2 119.05(18) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 121.3(2) . . ?
C9 C8 N2 118.82(19) . . ?
C13 C8 N2 119.9(2) . . ?
C8 C9 C10 119.0(2) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C11 C10 C9 120.5(2) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 119.6(2) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C13 120.7(2) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C8 C13 C12 118.8(2) . . ?
C8 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C19 C14 N1 121.10(19) . . ?
C19 C14 C15 119.61(19) . . ?
N1 C14 C15 119.24(18) . . ?
N2 C15 C16 123.71(19) . . ?
N2 C15 C14 117.52(18) . . ?
C16 C15 C14 118.77(18) . . ?
C15 C16 C17 119.12(19) . . ?
C15 C16 C20 127.77(17) . . ?
C17 C16 C20 112.82(17) . . ?
O3 C17 C18 122.89(18) . . ?
O3 C17 C16 114.43(18) . . ?
C18 C17 C16 122.66(19) . . ?
C17 C18 C19 117.42(18) . . ?
C17 C18 C27 120.77(19) . . ?
C19 C18 C27 121.78(19) . . ?
C14 C19 C18 122.22(19) . . ?
C14 C19 H19 118.9 . . ?
C18 C19 H19 118.9 . . ?
O1 C20 C21 121.20(19) . . ?
O1 C20 C16 117.06(19) . . ?
C21 C20 C16 121.46(17) . . ?
C26 C21 C22 118.6(2) . . ?
C26 C21 C20 121.19(19) . . ?
C22 C21 C20 120.15(19) . . ?
O2 C22 C23 118.4(2) . . ?
O2 C22 C21 121.3(2) . . ?
C23 C22 C21 120.3(2) . . ?
C24 C23 C22 119.7(2) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C25 120.9(2) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C26 C25 C24 119.4(2) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
C25 C26 C21 121.0(2) . . ?
C25 C26 H26 119.5 . . ?
C21 C26 H26 119.5 . . ?
O4 C27 C18 123.1(2) . . ?
O4 C27 C28 122.25(19) . . ?
C18 C27 C28 114.65(18) . . ?
C29 C28 C33 117.9(2) . . ?
C29 C28 C27 120.18(19) . . ?
C33 C28 C27 121.9(2) . . ?
O3 C29 C30 115.79(19) . . ?
O3 C29 C28 122.49(19) . . ?
C30 C29 C28 121.71(19) . . ?
C31 C30 C29 118.8(2) . . ?
C31 C30 H30 120.6 . . ?
C29 C30 H30 120.6 . . ?
C30 C31 C32 120.5(2) . . ?
C30 C31 H31 119.8 . . ?
C32 C31 H31 119.8 . . ?
C33 C32 C31 120.2(2) . . ?
C33 C32 H32 119.9 . . ?
C31 C32 H32 119.9 . . ?
C32 C33 C28 120.8(2) . . ?
C32 C33 H33 119.6 . . ?
C28 C33 H33 119.6 . . ?
C35 C34 C36 120.9(2) . 2_566 ?
C35 C34 H34 119.5 . . ?
C36 C34 H34 119.5 2_566 . ?
C34 C35 C36 119.5(3) . . ?
C34 C35 H35 120.2 . . ?
C36 C35 H35 120.2 . . ?
C34 C36 C35 119.6(3) 2_566 . ?
C34 C36 H36 120.2 2_566 . ?
C35 C36 H36 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 N1 C1 C2 -163.5(2) . . . . ?
C7 N1 C1 C2 7.0(3) . . . . ?
C14 N1 C1 C6 17.8(3) . . . . ?
C7 N1 C1 C6 -171.65(19) . . . . ?
N1 C1 C2 C3 -175.4(2) . . . . ?
C6 C1 C2 C3 3.3(3) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C2 C3 C4 C5 -1.5(4) . . . . ?
C3 C4 C5 C6 0.8(4) . . . . ?
C4 C5 C6 C1 1.9(3) . . . . ?
C4 C5 C6 N2 -179.6(2) . . . . ?
C2 C1 C6 C5 -3.9(3) . . . . ?
N1 C1 C6 C5 174.82(19) . . . . ?
C2 C1 C6 N2 177.51(19) . . . . ?
N1 C1 C6 N2 -3.8(3) . . . . ?
C15 N2 C6 C5 169.9(2) . . . . ?
C8 N2 C6 C5 -5.0(3) . . . . ?
C15 N2 C6 C1 -11.5(3) . . . . ?
C8 N2 C6 C1 173.57(19) . . . . ?
C15 N2 C8 C9 91.1(2) . . . . ?
C6 N2 C8 C9 -94.0(2) . . . . ?
C15 N2 C8 C13 -91.6(2) . . . . ?
C6 N2 C8 C13 83.4(2) . . . . ?
C13 C8 C9 C10 3.4(3) . . . . ?
N2 C8 C9 C10 -179.31(18) . . . . ?
C8 C9 C10 C11 -0.8(3) . . . . ?
C9 C10 C11 C12 -1.5(3) . . . . ?
C10 C11 C12 C13 1.1(3) . . . . ?
C9 C8 C13 C12 -3.7(3) . . . . ?
N2 C8 C13 C12 179.00(19) . . . . ?
C11 C12 C13 C8 1.4(3) . . . . ?
C1 N1 C14 C19 165.98(19) . . . . ?
C7 N1 C14 C19 -4.7(3) . . . . ?
C1 N1 C14 C15 -16.7(3) . . . . ?
C7 N1 C14 C15 172.67(19) . . . . ?
C6 N2 C15 C16 -167.66(19) . . . . ?
C8 N2 C15 C16 7.1(3) . . . . ?
C6 N2 C15 C14 12.5(3) . . . . ?
C8 N2 C15 C14 -172.77(18) . . . . ?
C19 C14 C15 N2 178.85(18) . . . . ?
N1 C14 C15 N2 1.5(3) . . . . ?
C19 C14 C15 C16 -1.0(3) . . . . ?
N1 C14 C15 C16 -178.40(18) . . . . ?
N2 C15 C16 C17 -175.95(19) . . . . ?
C14 C15 C16 C17 3.9(3) . . . . ?
N2 C15 C16 C20 10.6(3) . . . . ?
C14 C15 C16 C20 -169.49(19) . . . . ?
C29 O3 C17 C18 7.2(3) . . . . ?
C29 O3 C17 C16 -174.16(17) . . . . ?
C15 C16 C17 O3 178.36(18) . . . . ?
C20 C16 C17 O3 -7.3(3) . . . . ?
C15 C16 C17 C18 -2.9(3) . . . . ?
C20 C16 C17 C18 171.40(18) . . . . ?
O3 C17 C18 C19 177.56(18) . . . . ?
C16 C17 C18 C19 -1.0(3) . . . . ?
O3 C17 C18 C27 -4.0(3) . . . . ?
C16 C17 C18 C27 177.41(19) . . . . ?
N1 C14 C19 C18 174.24(19) . . . . ?
C15 C14 C19 C18 -3.1(3) . . . . ?
C17 C18 C19 C14 4.1(3) . . . . ?
C27 C18 C19 C14 -174.33(19) . . . . ?
C15 C16 C20 O1 87.1(3) . . . . ?
C17 C16 C20 O1 -86.6(2) . . . . ?
C15 C16 C20 C21 -98.9(3) . . . . ?
C17 C16 C20 C21 87.3(2) . . . . ?
O1 C20 C21 C26 178.85(18) . . . . ?
C16 C20 C21 C26 5.1(3) . . . . ?
O1 C20 C21 C22 -3.1(3) . . . . ?
C16 C20 C21 C22 -176.83(17) . . . . ?
C26 C21 C22 O2 -179.40(18) . . . . ?
C20 C21 C22 O2 2.5(3) . . . . ?
C26 C21 C22 C23 0.8(3) . . . . ?
C20 C21 C22 C23 -177.31(19) . . . . ?
O2 C22 C23 C24 -179.0(2) . . . . ?
C21 C22 C23 C24 0.8(3) . . . . ?
C22 C23 C24 C25 -1.9(4) . . . . ?
C23 C24 C25 C26 1.4(4) . . . . ?
C24 C25 C26 C21 0.2(3) . . . . ?
C22 C21 C26 C25 -1.3(3) . . . . ?
C20 C21 C26 C25 176.80(19) . . . . ?
C17 C18 C27 O4 178.8(2) . . . . ?
C19 C18 C27 O4 -2.8(3) . . . . ?
C17 C18 C27 C28 -2.4(3) . . . . ?
C19 C18 C27 C28 175.98(19) . . . . ?
O4 C27 C28 C29 -175.6(2) . . . . ?
C18 C27 C28 C29 5.6(3) . . . . ?
O4 C27 C28 C33 5.1(3) . . . . ?
C18 C27 C28 C33 -173.70(19) . . . . ?
C17 O3 C29 C30 175.40(19) . . . . ?
C17 O3 C29 C28 -3.7(3) . . . . ?
C33 C28 C29 O3 176.56(18) . . . . ?
C27 C28 C29 O3 -2.8(3) . . . . ?
C33 C28 C29 C30 -2.4(3) . . . . ?
C27 C28 C29 C30 178.2(2) . . . . ?
O3 C29 C30 C31 -176.90(19) . . . . ?
C28 C29 C30 C31 2.2(3) . . . . ?
C29 C30 C31 C32 -0.3(3) . . . . ?
C30 C31 C32 C33 -1.1(4) . . . . ?
C31 C32 C33 C28 0.8(4) . . . . ?
C29 C28 C33 C32 0.9(3) . . . . ?
C27 C28 C33 C32 -179.8(2) . . . . ?
C36 C34 C35 C36 -0.3(5) 2_566 . . . ?
C34 C35 C36 C34 0.3(4) . . . 2_566 ?

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

#==============================================================================
# 
# h,k,l, Fc-squared, Fo-squared, sigma(Fo-squared) and status flag 
# 
_shelx_title                     ' ns420JL923c'
_shelx_refln_list_code           4
_shelx_F_calc_maximum            193.01
_reflns_d_resolution_high        0.8301

_shelx_F_squared_multiplier      1.000


#==============================================================================
#     End of CIF
#==============================================================================
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: benzene'
####################################################################### 
# 
# 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_ns410yumikoFK
_database_code_depnum_ccdc_archive 'CCDC 2291932'
loop_
_audit_author_name
_audit_author_address
'Noriyuki Suzuki'
;Sophia University
Japan
;
_audit_update_record             
;
2023-08-31 deposited with the CCDC.	2023-11-09 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C18 H16 N2 O3'
_chemical_formula_moiety         'C18 H16 N2 O3'
_chemical_formula_weight         308.34
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.89055(11)
_cell_length_b                   8.30596(12)
_cell_length_c                   22.2467(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1458.02(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3956
_cell_measurement_theta_min      3.96
_cell_measurement_theta_max      76.78
_cell_measurement_temperature    153
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648.00
_exptl_absorpt_coefficient_mu    0.793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.61a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.864
_exptl_absorpt_correction_T_max  0.888

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

_diffrn_ambient_temperature      153
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            5252
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_theta_max         68.160
_diffrn_reflns_theta_min         3.974
_diffrn_reflns_theta_full        68.160
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2558
_reflns_number_gt                2431
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# 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          0.0358
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.0883
_refine_ls_wR_factor_gt          0.0864
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         2558
_refine_ls_number_parameters     214
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0585P)²+0.0815P] 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         0.14
_refine_diff_density_min         -0.18
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  995 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.1(2)

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.77011(16) 0.78597(18) 0.34530(6) 0.0370(3) Uani 1 1 d . . .
O2 O 0.94191(13) 0.72909(16) 0.25249(6) 0.0336(3) Uani 1 1 d . . .
O3 O 0.87766(15) 0.37487(16) 0.07626(5) 0.0345(3) Uani 1 1 d . . .
N1 N 1.07950(15) 0.73574(16) 0.12460(6) 0.0255(3) Uani 1 1 d . . .
N2 N 1.13109(17) 0.47748(17) 0.04859(6) 0.0243(3) Uani 1 1 d . . .
C1 C 0.6350(2) 0.7282(2) 0.31473(7) 0.0268(3) Uani 1 1 d . . .
C2 C 0.4773(2) 0.7322(2) 0.34312(8) 0.0299(4) Uani 1 1 d . . .
H2 H 0.4679 0.7732 0.3828 0.036 Uiso 1 1 calc R . .
C3 C 0.3353(2) 0.6768(2) 0.31357(8) 0.0317(4) Uani 1 1 d . . .
H3 H 0.2282 0.6806 0.3330 0.038 Uiso 1 1 calc R . .
C4 C 0.3470(2) 0.6158(2) 0.25582(8) 0.0320(4) Uani 1 1 d . . .
H4 H 0.2486 0.5773 0.2358 0.038 Uiso 1 1 calc R . .
C5 C 0.5025(2) 0.6112(2) 0.22749(7) 0.0279(4) Uani 1 1 d . . .
H5 H 0.5097 0.5696 0.1878 0.033 Uiso 1 1 calc R . .
C6 C 0.65012(19) 0.66633(18) 0.25586(7) 0.0239(3) Uani 1 1 d . . .
C7 C 0.81720(19) 0.6686(2) 0.22588(7) 0.0256(3) Uani 1 1 d . . .
C8 C 0.83636(19) 0.5934(2) 0.16746(7) 0.0260(3) Uani 1 1 d . . .
H8 H 0.7461 0.5257 0.1549 0.031 Uiso 1 1 calc R . .
C9 C 0.96913(18) 0.60871(19) 0.12839(7) 0.0235(3) Uani 1 1 d . . .
C10 C 0.98759(19) 0.4775(2) 0.08252(7) 0.0234(3) Uani 1 1 d . . .
C11 C 1.0340(2) 0.8932(2) 0.14902(9) 0.0382(4) Uani 1 1 d . . .
H11A H 0.9103 0.9021 0.1515 0.046 Uiso 1 1 calc R . .
H11B H 1.0780 0.9780 0.1227 0.046 Uiso 1 1 calc R . .
H11C H 1.0830 0.9052 0.1892 0.046 Uiso 1 1 calc R . .
C12 C 1.1548(2) 0.3429(2) 0.00739(8) 0.0343(4) Uani 1 1 d . . .
H12A H 1.2192 0.2577 0.0275 0.041 Uiso 1 1 calc R . .
H12B H 1.2171 0.3796 -0.0282 0.041 Uiso 1 1 calc R . .
H12C H 1.0439 0.3010 -0.0049 0.041 Uiso 1 1 calc R . .
C13 C 1.2374(2) 0.7178(2) 0.09658(7) 0.0246(3) Uani 1 1 d . . .
C14 C 1.3673(2) 0.8292(2) 0.10578(8) 0.0355(4) Uani 1 1 d . . .
H14 H 1.3485 0.9205 0.1306 0.043 Uiso 1 1 calc R . .
C15 C 1.5231(2) 0.8070(3) 0.07879(9) 0.0392(5) Uani 1 1 d . . .
H15 H 1.6111 0.8831 0.0852 0.047 Uiso 1 1 calc R . .
C16 C 1.5520(2) 0.6751(3) 0.04254(9) 0.0392(4) Uani 1 1 d . . .
H16 H 1.6598 0.6603 0.0243 0.047 Uiso 1 1 calc R . .
C17 C 1.4238(2) 0.5643(2) 0.03274(8) 0.0330(4) Uani 1 1 d . . .
H17 H 1.4442 0.4736 0.0078 0.040 Uiso 1 1 calc R . .
C18 C 1.26515(19) 0.5847(2) 0.05919(7) 0.0247(3) Uani 1 1 d . . .
H1 H 0.859(3) 0.770(3) 0.3192(13) 0.063(7) Uiso 1 1 d . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.42.61a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.61a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.61a (Rigaku OD, 2022)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (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 C1 1.352(2) . ?
O1 H1 0.92(3) . ?
O2 C7 1.2533(19) . ?
O3 C10 1.224(2) . ?
N1 C9 1.371(2) . ?
N1 C13 1.401(2) . ?
N1 C11 1.461(2) . ?
N2 C10 1.361(2) . ?
N2 C18 1.403(2) . ?
N2 C12 1.457(2) . ?
C1 C2 1.396(2) . ?
C1 C6 1.412(2) . ?
C2 C3 1.379(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.402(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.478(2) . ?
C7 C8 1.450(2) . ?
C8 C9 1.367(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.500(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.396(2) . ?
C13 C18 1.400(2) . ?
C14 C15 1.381(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.379(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.394(2) . ?
C17 H17 0.9500 . ?

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 O1 H1 103.4(17) . . ?
C9 N1 C13 120.68(14) . . ?
C9 N1 C11 120.66(13) . . ?
C13 N1 C11 118.65(14) . . ?
C10 N2 C18 122.29(13) . . ?
C10 N2 C12 117.09(14) . . ?
C18 N2 C12 119.73(13) . . ?
O1 C1 C2 117.80(14) . . ?
O1 C1 C6 121.96(15) . . ?
C2 C1 C6 120.24(15) . . ?
C3 C2 C1 120.07(15) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.72(15) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 119.55(16) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 121.61(15) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 117.81(14) . . ?
C5 C6 C7 122.84(13) . . ?
C1 C6 C7 119.29(14) . . ?
O2 C7 C8 120.93(14) . . ?
O2 C7 C6 119.50(14) . . ?
C8 C7 C6 119.48(13) . . ?
C9 C8 C7 127.58(15) . . ?
C9 C8 H8 116.2 . . ?
C7 C8 H8 116.2 . . ?
C8 C9 N1 126.68(14) . . ?
C8 C9 C10 116.07(13) . . ?
N1 C9 C10 117.12(13) . . ?
O3 C10 N2 121.79(14) . . ?
O3 C10 C9 120.96(13) . . ?
N2 C10 C9 117.26(13) . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 N1 121.12(15) . . ?
C14 C13 C18 119.72(15) . . ?
N1 C13 C18 119.15(14) . . ?
C15 C14 C13 120.09(18) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C14 120.50(17) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 119.95(16) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C18 120.58(17) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 N2 121.95(15) . . ?
C17 C18 C13 119.14(15) . . ?
N2 C18 C13 118.90(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 179.10(16) . . . . ?
C6 C1 C2 C3 -0.5(2) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C4 C5 C6 C1 -0.3(2) . . . . ?
C4 C5 C6 C7 -177.63(16) . . . . ?
O1 C1 C6 C5 -179.14(15) . . . . ?
C2 C1 C6 C5 0.4(2) . . . . ?
O1 C1 C6 C7 -1.7(2) . . . . ?
C2 C1 C6 C7 177.82(14) . . . . ?
C5 C6 C7 O2 175.43(15) . . . . ?
C1 C6 C7 O2 -1.8(2) . . . . ?
C5 C6 C7 C8 -7.8(2) . . . . ?
C1 C6 C7 C8 174.98(15) . . . . ?
O2 C7 C8 C9 -16.4(3) . . . . ?
C6 C7 C8 C9 166.83(16) . . . . ?
C7 C8 C9 N1 -25.3(3) . . . . ?
C7 C8 C9 C10 159.04(15) . . . . ?
C13 N1 C9 C8 160.34(16) . . . . ?
C11 N1 C9 C8 -20.4(2) . . . . ?
C13 N1 C9 C10 -24.1(2) . . . . ?
C11 N1 C9 C10 155.15(16) . . . . ?
C18 N2 C10 O3 -173.70(15) . . . . ?
C12 N2 C10 O3 -4.5(2) . . . . ?
C18 N2 C10 C9 6.2(2) . . . . ?
C12 N2 C10 C9 175.36(14) . . . . ?
C8 C9 C10 O3 8.7(2) . . . . ?
N1 C9 C10 O3 -167.36(15) . . . . ?
C8 C9 C10 N2 -171.14(14) . . . . ?
N1 C9 C10 N2 12.8(2) . . . . ?
C9 N1 C13 C14 -163.00(15) . . . . ?
C11 N1 C13 C14 17.8(2) . . . . ?
C9 N1 C13 C18 16.4(2) . . . . ?
C11 N1 C13 C18 -162.79(16) . . . . ?
N1 C13 C14 C15 178.51(16) . . . . ?
C18 C13 C14 C15 -0.9(3) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C14 C15 C16 C17 0.4(3) . . . . ?
C15 C16 C17 C18 0.1(3) . . . . ?
C16 C17 C18 N2 177.88(15) . . . . ?
C16 C17 C18 C13 -0.9(2) . . . . ?
C10 N2 C18 C17 167.01(15) . . . . ?
C12 N2 C18 C17 -1.9(2) . . . . ?
C10 N2 C18 C13 -14.2(2) . . . . ?
C12 N2 C18 C13 176.86(15) . . . . ?
C14 C13 C18 C17 1.3(2) . . . . ?
N1 C13 C18 C17 -178.13(14) . . . . ?
C14 C13 C18 N2 -177.49(15) . . . . ?
N1 C13 C18 N2 3.1(2) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 O2 . . . 2.5147(18) 0.92(3) 1.66(3) 154(3) no

#==============================================================================
# 
# h,k,l, Fc-squared, Fo-squared, sigma(Fo-squared) and status flag 
# 
_shelx_title                     ' ns410yumikoFK'
_shelx_refln_list_code           4
_shelx_F_calc_maximum            113.19
_reflns_d_resolution_high        0.8306

_shelx_F_squared_multiplier      1.000


#==============================================================================
#     End of CIF
#==============================================================================
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
####################################################################### 
# 
# 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_ns418JL917
_database_code_depnum_ccdc_archive 'CCDC 2291930'
loop_
_audit_author_name
_audit_author_address
'Noriyuki Suzuki'
;Sophia University
Japan
;
_audit_update_record             
;
2023-08-31 deposited with the CCDC.	2023-11-09 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C16 H12 N O2 S'
_chemical_formula_moiety         'C16 H12 N O2 S'
_chemical_formula_weight         282.34
_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                   7.0044(4)
_cell_length_b                   8.4419(3)
_cell_length_c                   11.6565(4)
_cell_angle_alpha                96.906(3)
_cell_angle_beta                 95.814(4)
_cell_angle_gamma                109.537(4)
_cell_volume                     637.44(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4282
_cell_measurement_theta_min      3.86
_cell_measurement_theta_max      77.16
_cell_measurement_temperature    153
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             294.00
_exptl_absorpt_coefficient_mu    2.258
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.702
_exptl_absorpt_correction_T_max  0.914

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

_diffrn_ambient_temperature      153
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            6530
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_theta_max         68.240
_diffrn_reflns_theta_min         3.864
_diffrn_reflns_theta_full        68.240
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2317
_reflns_number_gt                2152
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# 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          0.0395
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.1063
_refine_ls_wR_factor_gt          0.1038
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2317
_refine_ls_number_parameters     182
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0582P)²+0.2102P] 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          0.004
_refine_diff_density_max         0.47
_refine_diff_density_min         -0.34
_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)
;
S S 0.3331 0.5567
;
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.19318(6) 0.21261(5) 0.55615(3) 0.02098(16) Uani 1 1 d . . .
O1 O 0.1748(2) 0.42882(18) 0.16427(11) 0.0380(4) Uani 1 1 d . . .
O2 O 0.19224(19) 0.35468(15) 0.36445(10) 0.0279(3) Uani 1 1 d . . .
N1 N 0.2940(2) 0.46365(17) 0.72530(12) 0.0210(3) Uani 1 1 d . . .
C1 C 0.2231(3) 0.5931(2) 0.21473(15) 0.0264(4) Uani 1 1 d . . .
C2 C 0.2556(2) 0.6411(2) 0.33707(14) 0.0215(4) Uani 1 1 d . . .
C3 C 0.3032(2) 0.8139(2) 0.38230(15) 0.0241(4) Uani 1 1 d . . .
H3 H 0.3245 0.8486 0.4646 0.029 Uiso 1 1 calc R . .
C4 C 0.3198(3) 0.9346(2) 0.31004(16) 0.0286(4) Uani 1 1 d . . .
H4 H 0.3520 1.0509 0.3423 0.034 Uiso 1 1 calc R . .
C5 C 0.2890(3) 0.8842(3) 0.18982(17) 0.0313(4) Uani 1 1 d . . .
H5 H 0.3021 0.9670 0.1398 0.038 Uiso 1 1 calc R . .
C6 C 0.2397(3) 0.7160(3) 0.14229(16) 0.0322(4) Uani 1 1 d . . .
H6 H 0.2169 0.6830 0.0598 0.039 Uiso 1 1 calc R . .
C7 C 0.2397(2) 0.5085(2) 0.41265(15) 0.0210(4) Uani 1 1 d . . .
C8 C 0.2779(2) 0.5527(2) 0.53554(15) 0.0212(4) Uani 1 1 d . . .
H8 H 0.3159 0.6688 0.5702 0.025 Uiso 1 1 calc R . .
C9 C 0.2611(2) 0.4301(2) 0.60652(14) 0.0198(3) Uani 1 1 d . . .
C10 C 0.3538(3) 0.6363(2) 0.78926(16) 0.0318(4) Uani 1 1 d . . .
H10A H 0.4688 0.7119 0.7580 0.038 Uiso 1 1 calc R . .
H10B H 0.3953 0.6370 0.8722 0.038 Uiso 1 1 calc R . .
H10C H 0.2376 0.6761 0.7806 0.038 Uiso 1 1 calc R . .
C11 C 0.2587(2) 0.3208(2) 0.78023(14) 0.0199(3) Uani 1 1 d . . .
C12 C 0.2039(2) 0.1711(2) 0.69984(14) 0.0202(3) Uani 1 1 d . . .
C13 C 0.1596(3) 0.0142(2) 0.73658(15) 0.0242(4) Uani 1 1 d . . .
H13 H 0.1242 -0.0876 0.6816 0.029 Uiso 1 1 calc R . .
C14 C 0.1683(3) 0.0092(2) 0.85546(15) 0.0261(4) Uani 1 1 d . . .
H14 H 0.1379 -0.0970 0.8825 0.031 Uiso 1 1 calc R . .
C15 C 0.2212(3) 0.1592(2) 0.93554(15) 0.0262(4) Uani 1 1 d . . .
H15 H 0.2254 0.1532 1.0166 0.031 Uiso 1 1 calc R . .
C16 C 0.2680(3) 0.3169(2) 0.89988(15) 0.0243(4) Uani 1 1 d . . .
H16 H 0.3051 0.4186 0.9550 0.029 Uiso 1 1 calc R . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (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
S1 C9 1.7445(17) . ?
S1 C12 1.7513(17) . ?
O1 C1 1.354(2) . ?
O2 C7 1.269(2) . ?
N1 C9 1.359(2) . ?
N1 C11 1.395(2) . ?
N1 C10 1.457(2) . ?
C1 C6 1.397(3) . ?
C1 C2 1.408(2) . ?
C2 C3 1.404(2) . ?
C2 C7 1.488(2) . ?
C3 C4 1.382(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.374(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.411(2) . ?
C8 C9 1.383(2) . ?
C8 H8 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.393(2) . ?
C11 C16 1.394(2) . ?
C12 C13 1.387(2) . ?
C13 C14 1.387(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.394(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.386(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?

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
C9 S1 C12 90.84(8) . . ?
C9 N1 C11 115.08(13) . . ?
C9 N1 C10 121.85(14) . . ?
C11 N1 C10 123.02(13) . . ?
O1 C1 C6 118.38(16) . . ?
O1 C1 C2 121.51(16) . . ?
C6 C1 C2 120.11(17) . . ?
C3 C2 C1 117.93(15) . . ?
C3 C2 C7 122.85(15) . . ?
C1 C2 C7 119.22(16) . . ?
C4 C3 C2 121.60(16) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 119.31(18) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.76(17) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 120.29(17) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
O2 C7 C8 120.51(15) . . ?
O2 C7 C2 118.73(15) . . ?
C8 C7 C2 120.76(15) . . ?
C9 C8 C7 121.18(15) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
N1 C9 C8 124.24(15) . . ?
N1 C9 S1 110.99(12) . . ?
C8 C9 S1 124.77(13) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 120.95(15) . . ?
C12 C11 N1 111.83(14) . . ?
C16 C11 N1 127.20(15) . . ?
C13 C12 C11 120.95(15) . . ?
C13 C12 S1 127.82(13) . . ?
C11 C12 S1 111.20(13) . . ?
C12 C13 C14 118.43(16) . . ?
C12 C13 H13 120.8 . . ?
C14 C13 H13 120.8 . . ?
C13 C14 C15 120.42(16) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 121.63(16) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C15 C16 C11 117.62(16) . . ?
C15 C16 H16 121.2 . . ?
C11 C16 H16 121.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -179.42(15) . . . . ?
C6 C1 C2 C3 0.4(2) . . . . ?
O1 C1 C2 C7 1.0(2) . . . . ?
C6 C1 C2 C7 -179.22(15) . . . . ?
C1 C2 C3 C4 -0.5(2) . . . . ?
C7 C2 C3 C4 179.06(15) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
C4 C5 C6 C1 -1.0(3) . . . . ?
O1 C1 C6 C5 -179.81(16) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
C3 C2 C7 O2 178.71(15) . . . . ?
C1 C2 C7 O2 -1.7(2) . . . . ?
C3 C2 C7 C8 -1.7(2) . . . . ?
C1 C2 C7 C8 177.90(14) . . . . ?
O2 C7 C8 C9 -1.2(2) . . . . ?
C2 C7 C8 C9 179.21(14) . . . . ?
C11 N1 C9 C8 176.83(14) . . . . ?
C10 N1 C9 C8 -0.9(3) . . . . ?
C11 N1 C9 S1 -2.65(18) . . . . ?
C10 N1 C9 S1 179.66(13) . . . . ?
C7 C8 C9 N1 -179.41(14) . . . . ?
C7 C8 C9 S1 0.0(2) . . . . ?
C12 S1 C9 N1 1.63(12) . . . . ?
C12 S1 C9 C8 -177.85(15) . . . . ?
C9 N1 C11 C12 2.5(2) . . . . ?
C10 N1 C11 C12 -179.87(15) . . . . ?
C9 N1 C11 C16 -175.77(15) . . . . ?
C10 N1 C11 C16 1.9(3) . . . . ?
C16 C11 C12 C13 -0.8(2) . . . . ?
N1 C11 C12 C13 -179.16(14) . . . . ?
C16 C11 C12 S1 177.24(13) . . . . ?
N1 C11 C12 S1 -1.12(17) . . . . ?
C9 S1 C12 C13 177.60(16) . . . . ?
C9 S1 C12 C11 -0.27(12) . . . . ?
C11 C12 C13 C14 0.9(2) . . . . ?
S1 C12 C13 C14 -176.82(12) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 C16 -0.4(3) . . . . ?
C14 C15 C16 C11 0.5(3) . . . . ?
C12 C11 C16 C15 0.1(2) . . . . ?
N1 C11 C16 C15 178.18(15) . . . . ?

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

#==============================================================================
# 
# h,k,l, Fc-squared, Fo-squared, sigma(Fo-squared) and status flag 
# 
_shelx_title                     ' ns418JL917'
_shelx_refln_list_code           4
_shelx_F_calc_maximum            156.20
_reflns_d_resolution_high        0.8301

_shelx_F_squared_multiplier      1.000


#==============================================================================
#     End of CIF
#==============================================================================
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloroethane'
####################################################################### 
# 
# 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_ns416JL847
_database_code_depnum_ccdc_archive 'CCDC 2291931'
loop_
_audit_author_name
_audit_author_address
'Noriyuki Suzuki'
;Sophia University
Japan
;
_audit_update_record             
;
2023-08-31 deposited with the CCDC.	2023-11-09 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C18 H15 Br N2 O3'
_chemical_formula_moiety         'C18 H15 Br N2 O3'
_chemical_formula_weight         387.23
_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                   8.9075(4)
_cell_length_b                   9.0424(5)
_cell_length_c                   10.1037(4)
_cell_angle_alpha                106.034(4)
_cell_angle_beta                 92.104(3)
_cell_angle_gamma                97.174(4)
_cell_volume                     773.86(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7286
_cell_measurement_theta_min      4.55
_cell_measurement_theta_max      77.00
_cell_measurement_temperature    153
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392.00
_exptl_absorpt_coefficient_mu    3.799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.61a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.472
_exptl_absorpt_correction_T_max  0.545

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

_diffrn_ambient_temperature      153
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            8649
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_theta_max         68.240
_diffrn_reflns_theta_min         4.566
_diffrn_reflns_theta_full        68.240
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2819
_reflns_number_gt                2724
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# 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          0.0297
_refine_ls_R_factor_gt           0.0287
_refine_ls_wR_factor_ref         0.0729
_refine_ls_wR_factor_gt          0.0723
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2819
_refine_ls_number_parameters     220
_refine_ls_goodness_of_fit_ref   1.209
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0275P)²+0.4676P] 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          0.001
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.56
_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)
;
Br Br -0.6763 1.2805
;
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)
;
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.18975(2) 0.62037(3) 0.43717(2) 0.02740(10) Uani 1 1 d . . .
O1 O 0.55216(18) -0.01651(17) 0.18883(16) 0.0250(3) Uani 1 1 d . . .
O2 O 0.83706(17) 0.48182(17) 0.19723(16) 0.0222(3) Uani 1 1 d . . .
O3 O 0.86260(18) 0.73486(18) 0.38904(17) 0.0266(4) Uani 1 1 d . . .
H3A H 0.8921 0.6604 0.3307 0.032 Uiso 1 1 calc R . .
N1 N 0.7114(2) -0.11172(19) 0.02580(18) 0.0179(4) Uani 1 1 d . . .
N2 N 0.7563(2) 0.17564(19) -0.02598(18) 0.0169(4) Uani 1 1 d . . .
C1 C 0.8076(2) -0.0903(2) -0.0761(2) 0.0178(4) Uani 1 1 d . . .
C2 C 0.8823(3) -0.2097(2) -0.1510(2) 0.0231(5) Uani 1 1 d . . .
H2 H 0.8695 -0.3075 -0.1320 0.028 Uiso 1 1 calc R . .
C3 C 0.9748(3) -0.1871(3) -0.2528(2) 0.0267(5) Uani 1 1 d . . .
H3 H 1.0245 -0.2694 -0.3037 0.032 Uiso 1 1 calc R . .
C4 C 0.9951(3) -0.0445(3) -0.2806(2) 0.0260(5) Uani 1 1 d . . .
H4 H 1.0590 -0.0290 -0.3502 0.031 Uiso 1 1 calc R . .
C5 C 0.9220(2) 0.0755(2) -0.2066(2) 0.0218(4) Uani 1 1 d . . .
H5 H 0.9359 0.1730 -0.2261 0.026 Uiso 1 1 calc R . .
C6 C 0.8282(2) 0.0542(2) -0.1037(2) 0.0174(4) Uani 1 1 d . . .
C7 C 0.6882(3) -0.2624(2) 0.0551(2) 0.0242(5) Uani 1 1 d . . .
H7A H 0.6245 -0.2559 0.1330 0.029 Uiso 1 1 calc R . .
H7B H 0.7865 -0.2905 0.0783 0.029 Uiso 1 1 calc R . .
H7C H 0.6380 -0.3417 -0.0265 0.029 Uiso 1 1 calc R . .
C8 C 0.7505(3) 0.3114(2) -0.0772(2) 0.0247(5) Uani 1 1 d . . .
H8A H 0.8467 0.3813 -0.0503 0.030 Uiso 1 1 calc R . .
H8B H 0.6672 0.3662 -0.0376 0.030 Uiso 1 1 calc R . .
H8C H 0.7338 0.2775 -0.1781 0.030 Uiso 1 1 calc R . .
C9 C 0.6417(2) 0.0046(2) 0.1048(2) 0.0174(4) Uani 1 1 d . . .
C10 C 0.6821(2) 0.1633(2) 0.0860(2) 0.0165(4) Uani 1 1 d . . .
C11 C 0.6326(2) 0.2835(2) 0.1830(2) 0.0179(4) Uani 1 1 d . . .
H11 H 0.5413 0.2596 0.2232 0.021 Uiso 1 1 calc R . .
C12 C 0.7058(2) 0.4413(2) 0.2289(2) 0.0175(4) Uani 1 1 d . . .
C13 C 0.6281(2) 0.5597(2) 0.3246(2) 0.0164(4) Uani 1 1 d . . .
C14 C 0.7126(2) 0.7022(2) 0.4001(2) 0.0195(4) Uani 1 1 d . . .
C15 C 0.6410(3) 0.8149(2) 0.4899(2) 0.0242(5) Uani 1 1 d . . .
H15 H 0.6991 0.9092 0.5435 0.029 Uiso 1 1 calc R . .
C16 C 0.4873(3) 0.7898(2) 0.5007(2) 0.0230(5) Uani 1 1 d . . .
H16 H 0.4387 0.8673 0.5602 0.028 Uiso 1 1 calc R . .
C17 C 0.4036(2) 0.6508(2) 0.4242(2) 0.0195(4) Uani 1 1 d . . .
C18 C 0.4712(2) 0.5353(2) 0.3383(2) 0.0173(4) Uani 1 1 d . . .
H18 H 0.4121 0.4398 0.2887 0.021 Uiso 1 1 calc R . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.42.61a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.61a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.61a (Rigaku OD, 2022)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (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
Br1 C17 1.905(2) . ?
O1 C9 1.222(3) . ?
O2 C12 1.260(3) . ?
O3 C14 1.348(3) . ?
O3 H3A 0.8400 . ?
N1 C9 1.366(3) . ?
N1 C1 1.402(3) . ?
N1 C7 1.464(3) . ?
N2 C10 1.355(3) . ?
N2 C6 1.403(3) . ?
N2 C8 1.464(3) . ?
C1 C2 1.395(3) . ?
C1 C6 1.401(3) . ?
C2 C3 1.383(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.397(3) . ?
C5 H5 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.500(3) . ?
C10 C11 1.378(3) . ?
C11 C12 1.434(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.491(3) . ?
C13 C18 1.405(3) . ?
C13 C14 1.407(3) . ?
C14 C15 1.401(3) . ?
C15 C16 1.373(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.379(3) . ?
C18 H18 0.9500 . ?

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
C14 O3 H3A 109.5 . . ?
C9 N1 C1 122.91(17) . . ?
C9 N1 C7 117.37(18) . . ?
C1 N1 C7 119.66(17) . . ?
C10 N2 C6 121.63(17) . . ?
C10 N2 C8 120.22(17) . . ?
C6 N2 C8 117.87(17) . . ?
C2 C1 C6 119.4(2) . . ?
C2 C1 N1 121.49(19) . . ?
C6 C1 N1 119.09(18) . . ?
C3 C2 C1 120.6(2) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 120.1(2) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 119.9(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 120.6(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 119.32(19) . . ?
C5 C6 N2 121.17(18) . . ?
C1 C6 N2 119.50(19) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C9 N1 122.65(18) . . ?
O1 C9 C10 120.62(18) . . ?
N1 C9 C10 116.73(18) . . ?
N2 C10 C11 125.90(18) . . ?
N2 C10 C9 118.29(17) . . ?
C11 C10 C9 115.73(18) . . ?
C10 C11 C12 126.18(19) . . ?
C10 C11 H11 116.9 . . ?
C12 C11 H11 116.9 . . ?
O2 C12 C11 122.29(18) . . ?
O2 C12 C13 118.75(18) . . ?
C11 C12 C13 118.84(18) . . ?
C18 C13 C14 118.77(18) . . ?
C18 C13 C12 121.81(18) . . ?
C14 C13 C12 119.39(18) . . ?
O3 C14 C15 118.05(19) . . ?
O3 C14 C13 121.88(19) . . ?
C15 C14 C13 120.1(2) . . ?
C16 C15 C14 120.3(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.61(19) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C18 C17 C16 121.6(2) . . ?
C18 C17 Br1 119.49(16) . . ?
C16 C17 Br1 118.95(16) . . ?
C17 C18 C13 119.63(19) . . ?
C17 C18 H18 120.2 . . ?
C13 C18 H18 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N1 C1 C2 177.19(19) . . . . ?
C7 N1 C1 C2 0.0(3) . . . . ?
C9 N1 C1 C6 -3.2(3) . . . . ?
C7 N1 C1 C6 179.64(18) . . . . ?
C6 C1 C2 C3 -0.7(3) . . . . ?
N1 C1 C2 C3 178.9(2) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C4 C5 C6 C1 -0.4(3) . . . . ?
C4 C5 C6 N2 178.6(2) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
N1 C1 C6 C5 -179.02(19) . . . . ?
C2 C1 C6 N2 -178.33(19) . . . . ?
N1 C1 C6 N2 2.0(3) . . . . ?
C10 N2 C6 C5 -170.9(2) . . . . ?
C8 N2 C6 C5 15.1(3) . . . . ?
C10 N2 C6 C1 8.0(3) . . . . ?
C8 N2 C6 C1 -165.98(19) . . . . ?
C1 N1 C9 O1 176.3(2) . . . . ?
C7 N1 C9 O1 -6.5(3) . . . . ?
C1 N1 C9 C10 -4.8(3) . . . . ?
C7 N1 C9 C10 172.49(18) . . . . ?
C6 N2 C10 C11 167.3(2) . . . . ?
C8 N2 C10 C11 -18.8(3) . . . . ?
C6 N2 C10 C9 -16.0(3) . . . . ?
C8 N2 C10 C9 157.83(19) . . . . ?
O1 C9 C10 N2 -166.77(19) . . . . ?
N1 C9 C10 N2 14.3(3) . . . . ?
O1 C9 C10 C11 10.2(3) . . . . ?
N1 C9 C10 C11 -168.73(19) . . . . ?
N2 C10 C11 C12 -33.6(3) . . . . ?
C9 C10 C11 C12 149.7(2) . . . . ?
C10 C11 C12 O2 -9.9(3) . . . . ?
C10 C11 C12 C13 174.0(2) . . . . ?
O2 C12 C13 C18 164.16(19) . . . . ?
C11 C12 C13 C18 -19.6(3) . . . . ?
O2 C12 C13 C14 -13.7(3) . . . . ?
C11 C12 C13 C14 162.53(19) . . . . ?
C18 C13 C14 O3 -178.20(18) . . . . ?
C12 C13 C14 O3 -0.3(3) . . . . ?
C18 C13 C14 C15 1.7(3) . . . . ?
C12 C13 C14 C15 179.68(19) . . . . ?
O3 C14 C15 C16 177.36(19) . . . . ?
C13 C14 C15 C16 -2.6(3) . . . . ?
C14 C15 C16 C17 1.3(3) . . . . ?
C15 C16 C17 C18 0.9(3) . . . . ?
C15 C16 C17 Br1 -178.45(16) . . . . ?
C16 C17 C18 C13 -1.7(3) . . . . ?
Br1 C17 C18 C13 177.63(14) . . . . ?
C14 C13 C18 C17 0.4(3) . . . . ?
C12 C13 C18 C17 -177.54(18) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O3 H3A Br1 . . 1_655 3.2753(17) 0.840 2.927 107.2 no
O3 H3A O2 . . . 2.536(2) 0.840 1.794 146.3 no

#==============================================================================
# 
# h,k,l, Fc-squared, Fo-squared, sigma(Fo-squared) and status flag 
# 
_shelx_title                     ' ns416JL847'
_shelx_refln_list_code           4
_shelx_F_calc_maximum            124.86
_reflns_d_resolution_high        0.8301

_shelx_F_squared_multiplier      1.000


#==============================================================================
#     End of CIF
#==============================================================================
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
####################################################################### 
# 
# 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_ns419JL946
_database_code_depnum_ccdc_archive 'CCDC 2291929'
loop_
_audit_author_name
_audit_author_address
'Noriyuki Suzuki'
;Sophia University
Japan
;
_audit_update_record             
;
2023-11-07 deposited with the CCDC.	2023-11-09 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C32 H28 N2 O5'
_chemical_formula_moiety         'C32 H28 N2 O5'
_chemical_formula_weight         520.58
_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 n 1'
_space_group_name_Hall           'P -2yac'
_space_group_IT_number           7
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2+X,-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   8.8903(2)
_cell_length_b                   11.6219(3)
_cell_length_c                   25.8312(6)
_cell_angle_alpha                90.0000
_cell_angle_beta                 97.715(2)
_cell_angle_gamma                90.0000
_cell_volume                     2644.78(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11195
_cell_measurement_theta_min      3.45
_cell_measurement_theta_max      77.09
_cell_measurement_temperature    153
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1096.00
_exptl_absorpt_coefficient_mu    0.721
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.813
_exptl_absorpt_correction_T_max  0.972

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

_diffrn_ambient_temperature      153
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54140
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            18280
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_theta_max         68.240
_diffrn_reflns_theta_min         3.452
_diffrn_reflns_theta_full        68.240
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             8131
_reflns_number_gt                7599
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# 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          0.1166
_refine_ls_R_factor_gt           0.1137
_refine_ls_wR_factor_ref         0.3305
_refine_ls_wR_factor_gt          0.3274
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         8131
_refine_ls_number_parameters     705
_refine_ls_goodness_of_fit_ref   1.545
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.2000P)²] 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          0.002
_refine_diff_density_max         1.30
_refine_diff_density_min         -0.43
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  3294 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.1(4)

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4666(5) 0.5951(4) 0.12035(17) 0.0323(9) Uani 1 1 d . . .
O2 O 0.5172(5) 0.4921(3) 0.23131(18) 0.0318(9) Uani 1 1 d . . .
O3 O 0.4336(6) 0.4971(4) 0.3215(2) 0.0453(12) Uani 1 1 d . . .
H3A H 0.4316 0.4781 0.2900 0.054 Uiso 1 1 calc R . .
O4 O 1.0075(5) 0.4887(4) 0.09657(19) 0.0330(9) Uani 1 1 d . . .
O5 O 0.9939(6) 0.3434(5) 0.0218(2) 0.0463(12) Uani 1 1 d . . .
H5A H 1.0354 0.3793 0.0482 0.056 Uiso 1 1 calc R . .
O6 O 1.0010(5) 0.7739(4) 0.21314(17) 0.0296(9) Uani 1 1 d . . .
O7 O 0.9649(5) 0.8733(3) 0.10359(17) 0.0302(9) Uani 1 1 d . . .
O8 O 0.8049(6) 0.8608(4) 0.0148(2) 0.0450(12) Uani 1 1 d . . .
H8 H 0.8292 0.8829 0.0458 0.054 Uiso 1 1 calc R . .
O9 O 1.5600(5) 0.8759(4) 0.23979(19) 0.0380(10) Uani 1 1 d . . .
O10 O 1.6082(6) 1.0090(5) 0.3191(2) 0.0504(13) Uani 1 1 d . . .
H10A H 1.6822 0.9694 0.3327 0.061 Uiso 1 1 calc R . .
N1 N 0.5166(5) 0.4052(4) 0.11159(19) 0.0252(10) Uani 1 1 d . . .
N2 N 0.7894(5) 0.4261(4) 0.1760(2) 0.0251(10) Uani 1 1 d . . .
N3 N 1.0608(5) 0.9621(4) 0.22336(19) 0.0260(10) Uani 1 1 d . . .
N4 N 1.2878(5) 0.9381(4) 0.15929(18) 0.0245(10) Uani 1 1 d . . .
C1 C 0.6265(7) 0.3160(5) 0.1126(2) 0.0255(11) Uani 1 1 d . . .
C2 C 0.7645(6) 0.3268(5) 0.1457(2) 0.0245(11) Uani 1 1 d . . .
C3 C 0.8656(8) 0.2359(5) 0.1490(3) 0.0344(13) Uani 1 1 d . . .
H3 H 0.9563 0.2401 0.1730 0.041 Uiso 1 1 calc R . .
C4 C 0.8373(9) 0.1383(6) 0.1179(3) 0.0423(15) Uani 1 1 d . . .
H4 H 0.9083 0.0768 0.1207 0.051 Uiso 1 1 calc R . .
C5 C 0.7044(8) 0.1312(5) 0.0825(3) 0.0395(15) Uani 1 1 d . . .
H5 H 0.6864 0.0666 0.0600 0.047 Uiso 1 1 calc R . .
C6 C 0.5991(8) 0.2197(5) 0.0806(3) 0.0347(13) Uani 1 1 d . . .
H6 H 0.5073 0.2146 0.0572 0.042 Uiso 1 1 calc R . .
C7 C 0.3612(8) 0.3860(6) 0.0865(3) 0.0409(15) Uani 1 1 d . . .
H7A H 0.2935 0.4428 0.0993 0.049 Uiso 1 1 calc R . .
H7B H 0.3286 0.3084 0.0947 0.049 Uiso 1 1 calc R . .
H7C H 0.3573 0.3940 0.0485 0.049 Uiso 1 1 calc R . .
C8 C 0.9332(6) 0.4373(5) 0.2102(2) 0.0277(12) Uani 1 1 d . . .
H8A H 0.9644 0.5191 0.2113 0.033 Uiso 1 1 calc R . .
H8B H 1.0118 0.3928 0.1951 0.033 Uiso 1 1 calc R . .
C9 C 0.9271(7) 0.3959(5) 0.2656(2) 0.0312(13) Uani 1 1 d . . .
C10 C 1.0442(8) 0.4317(7) 0.3043(3) 0.0418(16) Uani 1 1 d . . .
H10 H 1.1194 0.4840 0.2958 0.050 Uiso 1 1 calc R . .
C11 C 1.0495(13) 0.3907(9) 0.3547(3) 0.065(3) Uani 1 1 d . . .
H11 H 1.1299 0.4124 0.3809 0.078 Uiso 1 1 calc R . .
C12 C 0.9333(16) 0.3158(10) 0.3667(3) 0.074(3) Uani 1 1 d . . .
H12 H 0.9329 0.2910 0.4018 0.089 Uiso 1 1 calc R . .
C13 C 0.8221(12) 0.2789(7) 0.3289(3) 0.056(2) Uani 1 1 d . . .
H13 H 0.7464 0.2269 0.3371 0.068 Uiso 1 1 calc R . .
C14 C 0.8211(9) 0.3190(6) 0.2771(3) 0.0425(16) Uani 1 1 d . . .
H14 H 0.7459 0.2920 0.2502 0.051 Uiso 1 1 calc R . .
C15 C 0.5533(7) 0.5128(5) 0.1284(2) 0.0248(11) Uani 1 1 d . . .
C16 C 0.7143(6) 0.5331(4) 0.1566(2) 0.0225(11) Uani 1 1 d . . .
C17 C 0.7033(7) 0.6155(5) 0.2028(2) 0.0268(12) Uani 1 1 d . . .
H17A H 0.8072 0.6344 0.2195 0.032 Uiso 1 1 calc R . .
H17B H 0.6548 0.6881 0.1891 0.032 Uiso 1 1 calc R . .
C18 C 0.6137(7) 0.5668(5) 0.2440(2) 0.0261(11) Uani 1 1 d . . .
C19 C 0.6418(7) 0.6114(5) 0.2977(2) 0.0279(12) Uani 1 1 d . . .
C20 C 0.5453(8) 0.5754(5) 0.3343(2) 0.0322(13) Uani 1 1 d . . .
C21 C 0.5673(9) 0.6186(6) 0.3843(3) 0.0416(15) Uani 1 1 d . . .
H21 H 0.5050 0.5919 0.4090 0.050 Uiso 1 1 calc R . .
C22 C 0.6748(9) 0.6975(7) 0.3992(3) 0.0439(16) Uani 1 1 d . . .
H22 H 0.6861 0.7270 0.4338 0.053 Uiso 1 1 calc R . .
C23 C 0.7718(8) 0.7374(6) 0.3635(3) 0.0409(15) Uani 1 1 d . . .
H23 H 0.8476 0.7935 0.3740 0.049 Uiso 1 1 calc R . .
C24 C 0.7541(8) 0.6934(6) 0.3136(3) 0.0352(13) Uani 1 1 d . . .
H24 H 0.8190 0.7190 0.2896 0.042 Uiso 1 1 calc R . .
C25 C 0.8060(7) 0.6007(5) 0.1183(2) 0.0260(11) Uani 1 1 d . . .
H25A H 0.7366 0.6541 0.0969 0.031 Uiso 1 1 calc R . .
H25B H 0.8858 0.6472 0.1390 0.031 Uiso 1 1 calc R . .
C26 C 0.8791(7) 0.5217(5) 0.0824(2) 0.0269(12) Uani 1 1 d . . .
C27 C 0.7922(7) 0.4763(5) 0.0341(2) 0.0302(12) Uani 1 1 d . . .
C28 C 0.8547(9) 0.3860(7) 0.0073(3) 0.0427(16) Uani 1 1 d . . .
C29 C 0.7699(10) 0.3362(8) -0.0359(3) 0.0511(19) Uani 1 1 d . . .
H29 H 0.8109 0.2742 -0.0535 0.061 Uiso 1 1 calc R . .
C30 C 0.6279(12) 0.3759(10) -0.0531(4) 0.066(3) Uani 1 1 d . . .
H30 H 0.5706 0.3403 -0.0825 0.080 Uiso 1 1 calc R . .
C31 C 0.5643(10) 0.4680(8) -0.0286(3) 0.0521(19) Uani 1 1 d . . .
H31 H 0.4659 0.4960 -0.0414 0.063 Uiso 1 1 calc R . .
C32 C 0.6485(8) 0.5170(6) 0.0147(2) 0.0355(14) Uani 1 1 d . . .
H32 H 0.6073 0.5799 0.0316 0.043 Uiso 1 1 calc R . .
C33 C 1.1708(6) 1.0489(5) 0.2218(2) 0.0250(11) Uani 1 1 d . . .
C34 C 1.2809(6) 1.0382(4) 0.1887(2) 0.0228(10) Uani 1 1 d . . .
C35 C 1.3838(8) 1.1289(5) 0.1855(3) 0.0342(13) Uani 1 1 d . . .
H35 H 1.4576 1.1231 0.1623 0.041 Uiso 1 1 calc R . .
C36 C 1.3787(8) 1.2255(5) 0.2155(4) 0.0442(17) Uani 1 1 d . . .
H36 H 1.4459 1.2875 0.2116 0.053 Uiso 1 1 calc R . .
C37 C 1.2774(9) 1.2342(6) 0.2513(3) 0.0444(17) Uani 1 1 d . . .
H37 H 1.2790 1.2994 0.2735 0.053 Uiso 1 1 calc R . .
C38 C 1.1723(7) 1.1459(5) 0.2545(3) 0.0325(13) Uani 1 1 d . . .
H38 H 1.1015 1.1514 0.2789 0.039 Uiso 1 1 calc R . .
C39 C 0.9264(8) 0.9848(5) 0.2490(3) 0.0360(14) Uani 1 1 d . . .
H39A H 0.8453 0.9311 0.2357 0.043 Uiso 1 1 calc R . .
H39B H 0.8919 1.0639 0.2415 0.043 Uiso 1 1 calc R . .
H39C H 0.9520 0.9746 0.2868 0.043 Uiso 1 1 calc R . .
C40 C 1.4071(6) 0.9221(5) 0.1263(2) 0.0264(11) Uani 1 1 d . . .
H40A H 1.4394 0.8405 0.1280 0.032 Uiso 1 1 calc R . .
H40B H 1.4958 0.9696 0.1402 0.032 Uiso 1 1 calc R . .
C41 C 1.3572(7) 0.9545(5) 0.0693(2) 0.0323(13) Uani 1 1 d . . .
C42 C 1.2383(8) 1.0296(6) 0.0543(3) 0.0397(15) Uani 1 1 d . . .
H42 H 1.1835 1.0614 0.0801 0.048 Uiso 1 1 calc R . .
C43 C 1.1980(10) 1.0592(8) 0.0021(3) 0.053(2) Uani 1 1 d . . .
H43 H 1.1151 1.1096 -0.0081 0.064 Uiso 1 1 calc R . .
C44 C 1.2823(12) 1.0131(9) -0.0352(3) 0.059(2) Uani 1 1 d . . .
H44 H 1.2559 1.0330 -0.0709 0.071 Uiso 1 1 calc R . .
C45 C 1.4021(13) 0.9397(9) -0.0211(3) 0.065(3) Uani 1 1 d . . .
H45 H 1.4607 0.9113 -0.0465 0.078 Uiso 1 1 calc R . .
C46 C 1.4360(9) 0.9075(7) 0.0316(3) 0.0423(15) Uani 1 1 d . . .
H46 H 1.5140 0.8528 0.0416 0.051 Uiso 1 1 calc R . .
C47 C 1.0834(6) 0.8550(4) 0.2053(2) 0.0215(10) Uani 1 1 d . . .
C48 C 1.2216(6) 0.8323(4) 0.1779(2) 0.0213(10) Uani 1 1 d . . .
C49 C 1.1743(7) 0.7520(5) 0.1317(2) 0.0256(11) Uani 1 1 d . . .
H49A H 1.2650 0.7342 0.1147 0.031 Uiso 1 1 calc R . .
H49B H 1.1375 0.6789 0.1451 0.031 Uiso 1 1 calc R . .
C50 C 1.0521(6) 0.7996(5) 0.0908(2) 0.0261(11) Uani 1 1 d . . .
C51 C 1.0364(7) 0.7534(5) 0.0374(2) 0.0293(12) Uani 1 1 d . . .
C52 C 0.9094(8) 0.7858(5) 0.0021(3) 0.0329(13) Uani 1 1 d . . .
C53 C 0.8867(9) 0.7396(6) -0.0484(3) 0.0407(16) Uani 1 1 d . . .
H53 H 0.7990 0.7596 -0.0718 0.049 Uiso 1 1 calc R . .
C54 C 0.9912(11) 0.6658(6) -0.0637(3) 0.0468(17) Uani 1 1 d . . .
H54 H 0.9772 0.6373 -0.0984 0.056 Uiso 1 1 calc R . .
C55 C 1.1179(10) 0.6308(6) -0.0298(3) 0.0445(16) Uani 1 1 d . . .
H55 H 1.1887 0.5778 -0.0408 0.053 Uiso 1 1 calc R . .
C56 C 1.1378(8) 0.6758(6) 0.0204(3) 0.0355(14) Uani 1 1 d . . .
H56 H 1.2238 0.6526 0.0439 0.043 Uiso 1 1 calc R . .
C57 C 1.3398(7) 0.7637(5) 0.2174(2) 0.0285(12) Uani 1 1 d . . .
H57A H 1.2844 0.7101 0.2378 0.034 Uiso 1 1 calc R . .
H57B H 1.4054 0.7173 0.1973 0.034 Uiso 1 1 calc R . .
C58 C 1.4389(7) 0.8418(5) 0.2546(2) 0.0263(11) Uani 1 1 d . . .
C59 C 1.3927(7) 0.8813(5) 0.3038(2) 0.0301(12) Uani 1 1 d . . .
C60 C 1.4780(8) 0.9665(6) 0.3338(3) 0.0376(14) Uani 1 1 d . . .
C61 C 1.4290(10) 1.0094(7) 0.3780(3) 0.0490(18) Uani 1 1 d . . .
H61 H 1.4868 1.0681 0.3970 0.059 Uiso 1 1 calc R . .
C62 C 1.3022(11) 0.9715(8) 0.3953(3) 0.0534(19) Uani 1 1 d . . .
H62 H 1.2710 1.0026 0.4261 0.064 Uiso 1 1 calc R . .
C63 C 1.2159(10) 0.8847(7) 0.3670(3) 0.0466(17) Uani 1 1 d . . .
H63 H 1.1261 0.8571 0.3789 0.056 Uiso 1 1 calc R . .
C64 C 1.2601(8) 0.8400(6) 0.3225(2) 0.0356(14) Uani 1 1 d . . .
H64 H 1.2016 0.7809 0.3040 0.043 Uiso 1 1 calc R . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (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 C15 1.228(7) . ?
O2 C18 1.233(7) . ?
O3 C20 1.355(8) . ?
O3 H3A 0.8400 . ?
O4 C26 1.213(8) . ?
O5 C28 1.339(10) . ?
O5 H5A 0.8400 . ?
O6 C47 1.228(7) . ?
O7 C50 1.230(7) . ?
O8 C52 1.346(8) . ?
O8 H8 0.8400 . ?
O9 C58 1.255(8) . ?
O10 C60 1.359(9) . ?
O10 H10A 0.8400 . ?
N1 C15 1.349(8) . ?
N1 C1 1.423(7) . ?
N1 C7 1.463(8) . ?
N2 C2 1.396(7) . ?
N2 C8 1.459(7) . ?
N2 C16 1.467(7) . ?
N3 C47 1.354(7) . ?
N3 C33 1.409(7) . ?
N3 C39 1.465(8) . ?
N4 C34 1.396(7) . ?
N4 C40 1.458(7) . ?
N4 C48 1.472(7) . ?
C1 C6 1.394(8) . ?
C1 C2 1.403(8) . ?
C2 C3 1.382(8) . ?
C3 C4 1.394(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(11) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(10) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.517(9) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C14 1.361(11) . ?
C9 C10 1.406(9) . ?
C10 C11 1.381(12) . ?
C10 H10 0.9500 . ?
C11 C12 1.417(17) . ?
C11 H11 0.9500 . ?
C12 C13 1.363(15) . ?
C12 H12 0.9500 . ?
C13 C14 1.415(11) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.535(8) . ?
C16 C17 1.543(8) . ?
C16 C25 1.575(8) . ?
C17 C18 1.522(8) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.470(8) . ?
C19 C24 1.402(9) . ?
C19 C20 1.423(9) . ?
C20 C21 1.375(10) . ?
C21 C22 1.343(11) . ?
C21 H21 0.9500 . ?
C22 C23 1.421(11) . ?
C22 H22 0.9500 . ?
C23 C24 1.376(10) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C26 1.511(8) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.475(9) . ?
C27 C32 1.391(9) . ?
C27 C28 1.411(10) . ?
C28 C29 1.386(11) . ?
C29 C30 1.361(15) . ?
C29 H29 0.9500 . ?
C30 C31 1.401(14) . ?
C30 H30 0.9500 . ?
C31 C32 1.382(11) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C34 1.390(8) . ?
C33 C38 1.406(8) . ?
C34 C35 1.405(8) . ?
C35 C36 1.368(10) . ?
C35 H35 0.9500 . ?
C36 C37 1.377(12) . ?
C36 H36 0.9500 . ?
C37 C38 1.399(10) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 C41 1.527(8) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 C46 1.385(10) . ?
C41 C42 1.386(11) . ?
C42 C43 1.391(11) . ?
C42 H42 0.9500 . ?
C43 C44 1.405(15) . ?
C43 H43 0.9500 . ?
C44 C45 1.375(16) . ?
C44 H44 0.9500 . ?
C45 C46 1.407(12) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C47 C48 1.519(7) . ?
C48 C49 1.530(7) . ?
C48 C57 1.578(7) . ?
C49 C50 1.514(8) . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C50 C51 1.469(8) . ?
C51 C56 1.388(9) . ?
C51 C52 1.404(9) . ?
C52 C53 1.400(10) . ?
C53 C54 1.361(11) . ?
C53 H53 0.9500 . ?
C54 C55 1.390(12) . ?
C54 H54 0.9500 . ?
C55 C56 1.387(10) . ?
C55 H55 0.9500 . ?
C56 H56 0.9500 . ?
C57 C58 1.515(8) . ?
C57 H57A 0.9900 . ?
C57 H57B 0.9900 . ?
C58 C59 1.461(9) . ?
C59 C60 1.413(9) . ?
C59 C64 1.417(9) . ?
C60 C61 1.369(12) . ?
C61 C62 1.342(14) . ?
C61 H61 0.9500 . ?
C62 C63 1.411(12) . ?
C62 H62 0.9500 . ?
C63 C64 1.365(11) . ?
C63 H63 0.9500 . ?
C64 H64 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 O3 H3A 109.5 . . ?
C28 O5 H5A 109.5 . . ?
C52 O8 H8 109.5 . . ?
C60 O10 H10A 109.5 . . ?
C15 N1 C1 122.3(5) . . ?
C15 N1 C7 117.2(5) . . ?
C1 N1 C7 120.2(5) . . ?
C2 N2 C8 118.2(5) . . ?
C2 N2 C16 118.6(5) . . ?
C8 N2 C16 117.0(4) . . ?
C47 N3 C33 120.9(5) . . ?
C47 N3 C39 119.3(5) . . ?
C33 N3 C39 119.6(5) . . ?
C34 N4 C40 120.8(5) . . ?
C34 N4 C48 118.0(4) . . ?
C40 N4 C48 116.1(4) . . ?
C6 C1 C2 120.1(6) . . ?
C6 C1 N1 120.6(5) . . ?
C2 C1 N1 119.2(5) . . ?
C3 C2 N2 123.0(6) . . ?
C3 C2 C1 118.5(5) . . ?
N2 C2 C1 118.3(5) . . ?
C2 C3 C4 121.4(7) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 119.8(7) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 119.1(6) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C1 120.7(6) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 C9 113.8(5) . . ?
N2 C8 H8A 108.8 . . ?
C9 C8 H8A 108.8 . . ?
N2 C8 H8B 108.8 . . ?
C9 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C14 C9 C10 120.5(7) . . ?
C14 C9 C8 121.9(6) . . ?
C10 C9 C8 117.4(6) . . ?
C11 C10 C9 119.8(8) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 119.1(8) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C13 C12 C11 121.0(8) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 119.2(9) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C9 C14 C13 120.4(7) . . ?
C9 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
O1 C15 N1 123.3(5) . . ?
O1 C15 C16 119.0(5) . . ?
N1 C15 C16 117.7(5) . . ?
N2 C16 C15 112.7(4) . . ?
N2 C16 C17 109.6(5) . . ?
C15 C16 C17 108.1(5) . . ?
N2 C16 C25 112.8(4) . . ?
C15 C16 C25 107.8(5) . . ?
C17 C16 C25 105.5(4) . . ?
C18 C17 C16 113.7(5) . . ?
C18 C17 H17A 108.8 . . ?
C16 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
C16 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
O2 C18 C19 121.5(5) . . ?
O2 C18 C17 119.1(5) . . ?
C19 C18 C17 119.3(5) . . ?
C24 C19 C20 118.3(6) . . ?
C24 C19 C18 122.8(6) . . ?
C20 C19 C18 118.9(5) . . ?
O3 C20 C21 118.9(6) . . ?
O3 C20 C19 121.4(5) . . ?
C21 C20 C19 119.7(6) . . ?
C22 C21 C20 121.6(7) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C21 C22 C23 120.6(6) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C24 C23 C22 118.9(6) . . ?
C24 C23 H23 120.6 . . ?
C22 C23 H23 120.6 . . ?
C23 C24 C19 121.0(6) . . ?
C23 C24 H24 119.5 . . ?
C19 C24 H24 119.5 . . ?
C26 C25 C16 112.6(4) . . ?
C26 C25 H25A 109.1 . . ?
C16 C25 H25A 109.1 . . ?
C26 C25 H25B 109.1 . . ?
C16 C25 H25B 109.1 . . ?
H25A C25 H25B 107.8 . . ?
O4 C26 C27 120.4(6) . . ?
O4 C26 C25 118.2(6) . . ?
C27 C26 C25 121.1(5) . . ?
C32 C27 C28 118.6(6) . . ?
C32 C27 C26 122.3(6) . . ?
C28 C27 C26 119.1(6) . . ?
O5 C28 C29 117.0(7) . . ?
O5 C28 C27 123.1(7) . . ?
C29 C28 C27 119.9(7) . . ?
C30 C29 C28 120.1(8) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C29 C30 C31 121.6(8) . . ?
C29 C30 H30 119.2 . . ?
C31 C30 H30 119.2 . . ?
C32 C31 C30 118.2(8) . . ?
C32 C31 H31 120.9 . . ?
C30 C31 H31 120.9 . . ?
C31 C32 C27 121.5(7) . . ?
C31 C32 H32 119.2 . . ?
C27 C32 H32 119.2 . . ?
C34 C33 C38 119.4(5) . . ?
C34 C33 N3 120.1(5) . . ?
C38 C33 N3 120.5(5) . . ?
C33 C34 N4 119.7(5) . . ?
C33 C34 C35 119.1(5) . . ?
N4 C34 C35 121.1(5) . . ?
C36 C35 C34 120.7(6) . . ?
C36 C35 H35 119.6 . . ?
C34 C35 H35 119.6 . . ?
C35 C36 C37 120.9(6) . . ?
C35 C36 H36 119.5 . . ?
C37 C36 H36 119.5 . . ?
C36 C37 C38 119.2(6) . . ?
C36 C37 H37 120.4 . . ?
C38 C37 H37 120.4 . . ?
C37 C38 C33 120.3(6) . . ?
C37 C38 H38 119.8 . . ?
C33 C38 H38 119.8 . . ?
N3 C39 H39A 109.5 . . ?
N3 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
N3 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
N4 C40 C41 113.1(5) . . ?
N4 C40 H40A 109.0 . . ?
C41 C40 H40A 109.0 . . ?
N4 C40 H40B 109.0 . . ?
C41 C40 H40B 109.0 . . ?
H40A C40 H40B 107.8 . . ?
C46 C41 C42 119.4(6) . . ?
C46 C41 C40 118.1(6) . . ?
C42 C41 C40 122.5(6) . . ?
C41 C42 C43 121.0(7) . . ?
C41 C42 H42 119.5 . . ?
C43 C42 H42 119.5 . . ?
C42 C43 C44 118.6(8) . . ?
C42 C43 H43 120.7 . . ?
C44 C43 H43 120.7 . . ?
C45 C44 C43 121.4(8) . . ?
C45 C44 H44 119.3 . . ?
C43 C44 H44 119.3 . . ?
C44 C45 C46 118.6(8) . . ?
C44 C45 H45 120.7 . . ?
C46 C45 H45 120.7 . . ?
C41 C46 C45 120.9(8) . . ?
C41 C46 H46 119.6 . . ?
C45 C46 H46 119.6 . . ?
O6 C47 N3 121.9(5) . . ?
O6 C47 C48 118.7(5) . . ?
N3 C47 C48 119.2(5) . . ?
N4 C48 C47 113.0(4) . . ?
N4 C48 C49 109.5(4) . . ?
C47 C48 C49 108.3(4) . . ?
N4 C48 C57 111.8(4) . . ?
C47 C48 C57 107.3(5) . . ?
C49 C48 C57 106.6(4) . . ?
C50 C49 C48 114.7(4) . . ?
C50 C49 H49A 108.6 . . ?
C48 C49 H49A 108.6 . . ?
C50 C49 H49B 108.6 . . ?
C48 C49 H49B 108.6 . . ?
H49A C49 H49B 107.6 . . ?
O7 C50 C51 121.5(5) . . ?
O7 C50 C49 119.1(5) . . ?
C51 C50 C49 119.3(5) . . ?
C56 C51 C52 117.9(6) . . ?
C56 C51 C50 123.4(6) . . ?
C52 C51 C50 118.6(5) . . ?
O8 C52 C53 117.3(6) . . ?
O8 C52 C51 122.4(6) . . ?
C53 C52 C51 120.3(6) . . ?
C54 C53 C52 119.5(7) . . ?
C54 C53 H53 120.2 . . ?
C52 C53 H53 120.2 . . ?
C53 C54 C55 121.9(7) . . ?
C53 C54 H54 119.0 . . ?
C55 C54 H54 119.0 . . ?
C56 C55 C54 117.9(7) . . ?
C56 C55 H55 121.0 . . ?
C54 C55 H55 121.0 . . ?
C55 C56 C51 122.3(6) . . ?
C55 C56 H56 118.9 . . ?
C51 C56 H56 118.9 . . ?
C58 C57 C48 112.8(4) . . ?
C58 C57 H57A 109.0 . . ?
C48 C57 H57A 109.0 . . ?
C58 C57 H57B 109.0 . . ?
C48 C57 H57B 109.0 . . ?
H57A C57 H57B 107.8 . . ?
O9 C58 C59 121.3(5) . . ?
O9 C58 C57 116.4(6) . . ?
C59 C58 C57 122.2(5) . . ?
C60 C59 C64 117.4(6) . . ?
C60 C59 C58 120.3(6) . . ?
C64 C59 C58 122.3(5) . . ?
O10 C60 C61 118.5(7) . . ?
O10 C60 C59 121.1(6) . . ?
C61 C60 C59 120.3(7) . . ?
C62 C61 C60 122.2(8) . . ?
C62 C61 H61 118.9 . . ?
C60 C61 H61 118.9 . . ?
C61 C62 C63 119.0(8) . . ?
C61 C62 H62 120.5 . . ?
C63 C62 H62 120.5 . . ?
C64 C63 C62 120.7(8) . . ?
C64 C63 H63 119.7 . . ?
C62 C63 H63 119.7 . . ?
C63 C64 C59 120.3(7) . . ?
C63 C64 H64 119.8 . . ?
C59 C64 H64 119.8 . . ?

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
C15 N1 C1 C6 -158.8(6) . . . . ?
C7 N1 C1 C6 14.1(8) . . . . ?
C15 N1 C1 C2 20.1(8) . . . . ?
C7 N1 C1 C2 -167.0(6) . . . . ?
C8 N2 C2 C3 4.1(8) . . . . ?
C16 N2 C2 C3 155.6(6) . . . . ?
C8 N2 C2 C1 -179.8(5) . . . . ?
C16 N2 C2 C1 -28.3(8) . . . . ?
C6 C1 C2 C3 -5.6(8) . . . . ?
N1 C1 C2 C3 175.5(5) . . . . ?
C6 C1 C2 N2 178.1(5) . . . . ?
N1 C1 C2 N2 -0.8(8) . . . . ?
N2 C2 C3 C4 -179.7(6) . . . . ?
C1 C2 C3 C4 4.3(9) . . . . ?
C2 C3 C4 C5 -0.1(11) . . . . ?
C3 C4 C5 C6 -2.9(11) . . . . ?
C4 C5 C6 C1 1.5(10) . . . . ?
C2 C1 C6 C5 2.8(9) . . . . ?
N1 C1 C6 C5 -178.4(6) . . . . ?
C2 N2 C8 C9 -93.8(6) . . . . ?
C16 N2 C8 C9 114.3(5) . . . . ?
N2 C8 C9 C14 23.0(8) . . . . ?
N2 C8 C9 C10 -162.8(5) . . . . ?
C14 C9 C10 C11 -1.6(11) . . . . ?
C8 C9 C10 C11 -175.9(7) . . . . ?
C9 C10 C11 C12 -2.0(13) . . . . ?
C10 C11 C12 C13 3.8(15) . . . . ?
C11 C12 C13 C14 -1.8(15) . . . . ?
C10 C9 C14 C13 3.6(11) . . . . ?
C8 C9 C14 C13 177.6(7) . . . . ?
C12 C13 C14 C9 -1.9(13) . . . . ?
C1 N1 C15 O1 168.1(5) . . . . ?
C7 N1 C15 O1 -5.1(9) . . . . ?
C1 N1 C15 C16 -9.1(8) . . . . ?
C7 N1 C15 C16 177.8(5) . . . . ?
C2 N2 C16 C15 37.2(7) . . . . ?
C8 N2 C16 C15 -170.9(5) . . . . ?
C2 N2 C16 C17 157.7(5) . . . . ?
C8 N2 C16 C17 -50.5(6) . . . . ?
C2 N2 C16 C25 -85.1(6) . . . . ?
C8 N2 C16 C25 66.7(6) . . . . ?
O1 C15 C16 N2 164.3(5) . . . . ?
N1 C15 C16 N2 -18.4(7) . . . . ?
O1 C15 C16 C17 43.1(7) . . . . ?
N1 C15 C16 C17 -139.7(5) . . . . ?
O1 C15 C16 C25 -70.6(6) . . . . ?
N1 C15 C16 C25 106.7(5) . . . . ?
N2 C16 C17 C18 -59.9(6) . . . . ?
C15 C16 C17 C18 63.2(6) . . . . ?
C25 C16 C17 C18 178.4(5) . . . . ?
C16 C17 C18 O2 -25.0(8) . . . . ?
C16 C17 C18 C19 156.3(5) . . . . ?
O2 C18 C19 C24 177.8(6) . . . . ?
C17 C18 C19 C24 -3.5(9) . . . . ?
O2 C18 C19 C20 -6.1(9) . . . . ?
C17 C18 C19 C20 172.6(5) . . . . ?
C24 C19 C20 O3 179.5(6) . . . . ?
C18 C19 C20 O3 3.2(9) . . . . ?
C24 C19 C20 C21 -2.0(9) . . . . ?
C18 C19 C20 C21 -178.3(6) . . . . ?
O3 C20 C21 C22 -179.0(7) . . . . ?
C19 C20 C21 C22 2.4(11) . . . . ?
C20 C21 C22 C23 -1.3(11) . . . . ?
C21 C22 C23 C24 -0.2(11) . . . . ?
C22 C23 C24 C19 0.6(10) . . . . ?
C20 C19 C24 C23 0.5(9) . . . . ?
C18 C19 C24 C23 176.6(6) . . . . ?
N2 C16 C25 C26 38.4(6) . . . . ?
C15 C16 C25 C26 -86.6(6) . . . . ?
C17 C16 C25 C26 158.0(5) . . . . ?
C16 C25 C26 O4 -91.2(6) . . . . ?
C16 C25 C26 C27 82.6(6) . . . . ?
O4 C26 C27 C32 -175.9(5) . . . . ?
C25 C26 C27 C32 10.4(8) . . . . ?
O4 C26 C27 C28 6.0(8) . . . . ?
C25 C26 C27 C28 -167.7(6) . . . . ?
C32 C27 C28 O5 177.9(6) . . . . ?
C26 C27 C28 O5 -4.0(10) . . . . ?
C32 C27 C28 C29 -3.2(10) . . . . ?
C26 C27 C28 C29 175.0(7) . . . . ?
O5 C28 C29 C30 -179.5(8) . . . . ?
C27 C28 C29 C30 1.5(13) . . . . ?
C28 C29 C30 C31 0.8(15) . . . . ?
C29 C30 C31 C32 -1.3(14) . . . . ?
C30 C31 C32 C27 -0.5(12) . . . . ?
C28 C27 C32 C31 2.7(9) . . . . ?
C26 C27 C32 C31 -175.4(6) . . . . ?
C47 N3 C33 C34 19.1(8) . . . . ?
C39 N3 C33 C34 -166.3(5) . . . . ?
C47 N3 C33 C38 -159.6(5) . . . . ?
C39 N3 C33 C38 15.0(8) . . . . ?
C38 C33 C34 N4 174.8(5) . . . . ?
N3 C33 C34 N4 -3.8(8) . . . . ?
C38 C33 C34 C35 -5.1(8) . . . . ?
N3 C33 C34 C35 176.2(5) . . . . ?
C40 N4 C34 C33 -176.8(5) . . . . ?
C48 N4 C34 C33 -23.0(7) . . . . ?
C40 N4 C34 C35 3.2(8) . . . . ?
C48 N4 C34 C35 156.9(5) . . . . ?
C33 C34 C35 C36 1.7(9) . . . . ?
N4 C34 C35 C36 -178.3(6) . . . . ?
C34 C35 C36 C37 3.0(11) . . . . ?
C35 C36 C37 C38 -4.0(12) . . . . ?
C36 C37 C38 C33 0.4(11) . . . . ?
C34 C33 C38 C37 4.1(9) . . . . ?
N3 C33 C38 C37 -177.2(6) . . . . ?
C34 N4 C40 C41 -96.5(6) . . . . ?
C48 N4 C40 C41 109.2(5) . . . . ?
N4 C40 C41 C46 -157.8(6) . . . . ?
N4 C40 C41 C42 22.9(8) . . . . ?
C46 C41 C42 C43 -0.6(10) . . . . ?
C40 C41 C42 C43 178.6(6) . . . . ?
C41 C42 C43 C44 -1.2(12) . . . . ?
C42 C43 C44 C45 0.3(14) . . . . ?
C43 C44 C45 C46 2.4(14) . . . . ?
C42 C41 C46 C45 3.4(11) . . . . ?
C40 C41 C46 C45 -175.9(7) . . . . ?
C44 C45 C46 C41 -4.3(13) . . . . ?
C33 N3 C47 O6 168.9(5) . . . . ?
C39 N3 C47 O6 -5.7(8) . . . . ?
C33 N3 C47 C48 -6.4(7) . . . . ?
C39 N3 C47 C48 179.0(5) . . . . ?
C34 N4 C48 C47 33.4(6) . . . . ?
C40 N4 C48 C47 -171.6(4) . . . . ?
C34 N4 C48 C49 154.2(5) . . . . ?
C40 N4 C48 C49 -50.8(6) . . . . ?
C34 N4 C48 C57 -87.9(6) . . . . ?
C40 N4 C48 C57 67.1(6) . . . . ?
O6 C47 C48 N4 165.6(5) . . . . ?
N3 C47 C48 N4 -18.9(7) . . . . ?
O6 C47 C48 C49 44.1(6) . . . . ?
N3 C47 C48 C49 -140.4(5) . . . . ?
O6 C47 C48 C57 -70.7(6) . . . . ?
N3 C47 C48 C57 104.8(5) . . . . ?
N4 C48 C49 C50 -62.8(6) . . . . ?
C47 C48 C49 C50 60.9(6) . . . . ?
C57 C48 C49 C50 176.1(5) . . . . ?
C48 C49 C50 O7 -24.8(7) . . . . ?
C48 C49 C50 C51 157.8(5) . . . . ?
O7 C50 C51 C56 175.7(6) . . . . ?
C49 C50 C51 C56 -6.9(9) . . . . ?
O7 C50 C51 C52 -6.7(8) . . . . ?
C49 C50 C51 C52 170.7(5) . . . . ?
C56 C51 C52 O8 -179.8(6) . . . . ?
C50 C51 C52 O8 2.5(9) . . . . ?
C56 C51 C52 C53 0.6(9) . . . . ?
C50 C51 C52 C53 -177.1(6) . . . . ?
O8 C52 C53 C54 178.2(7) . . . . ?
C51 C52 C53 C54 -2.1(10) . . . . ?
C52 C53 C54 C55 2.6(12) . . . . ?
C53 C54 C55 C56 -1.5(12) . . . . ?
C54 C55 C56 C51 0.0(11) . . . . ?
C52 C51 C56 C55 0.5(10) . . . . ?
C50 C51 C56 C55 178.1(6) . . . . ?
N4 C48 C57 C58 39.5(7) . . . . ?
C47 C48 C57 C58 -84.9(6) . . . . ?
C49 C48 C57 C58 159.2(5) . . . . ?
C48 C57 C58 O9 -89.8(6) . . . . ?
C48 C57 C58 C59 86.7(7) . . . . ?
O9 C58 C59 C60 5.2(9) . . . . ?
C57 C58 C59 C60 -171.1(5) . . . . ?
O9 C58 C59 C64 -177.0(6) . . . . ?
C57 C58 C59 C64 6.7(8) . . . . ?
C64 C59 C60 O10 178.7(6) . . . . ?
C58 C59 C60 O10 -3.5(9) . . . . ?
C64 C59 C60 C61 -2.5(10) . . . . ?
C58 C59 C60 C61 175.4(6) . . . . ?
O10 C60 C61 C62 -179.5(7) . . . . ?
C59 C60 C61 C62 1.6(12) . . . . ?
C60 C61 C62 C63 -0.2(12) . . . . ?
C61 C62 C63 C64 -0.2(12) . . . . ?
C62 C63 C64 C59 -0.8(11) . . . . ?
C60 C59 C64 C63 2.1(9) . . . . ?
C58 C59 C64 C63 -175.7(6) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O3 H3A O2 . . . 2.539(7) 0.840 1.793 146.9 no
O5 H5A O4 . . . 2.555(7) 0.840 1.823 144.7 no
O8 H8 O7 . . . 2.535(7) 0.840 1.792 146.3 no

#==============================================================================
# 
# h,k,l, Fc-squared, Fo-squared, sigma(Fo-squared) and status flag 
# 
_shelx_title                     ' ns419JL946'
_shelx_refln_list_code           4
_shelx_F_calc_maximum            148.26
_reflns_d_resolution_high        0.8298

_shelx_F_squared_multiplier      1.000


#==============================================================================
#     End of CIF
#==============================================================================
