# Supplementary Information (SI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_E-e7-S
_database_code_depnum_ccdc_archive 'CCDC 2431293'
loop_
_audit_author_name
_audit_author_address
'Isao Yoshikawa'
;Institute of Industrial Science, The University of Tokyo
Japan
;
_audit_update_record             
;
2025-03-14 deposited with the CCDC.	2025-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H30 N2 O4'
_chemical_formula_sum            'C23 H30 N2 O4'
_chemical_formula_weight         398.49

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   14.3138(8)
_cell_length_b                   4.9630(3)
_cell_length_c                   14.9598(9)
_cell_angle_alpha                90
_cell_angle_beta                 90.559(5)
_cell_angle_gamma                90
_cell_volume                     1062.68(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5004
_cell_measurement_theta_min      4.3220
_cell_measurement_theta_max      72.0790

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.060
_shelx_estimated_absorpt_T_min   0.853
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_coefficient_mu    0.673
_exptl_absorpt_correction_T_min  0.751
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.90 (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            8771
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.088
_diffrn_reflns_theta_max         72.455
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.794
_diffrn_reflns_point_group_measured_fraction_full 0.817
_reflns_number_total             3348
_reflns_number_gt                2950
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.447
_reflns_Friedel_fraction_max     0.558
_reflns_Friedel_fraction_full    0.586

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.90 (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.90 (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_refine_special_details          'Refined as a 2-component inversion twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1661P)²+3.1110P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.4(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3348
_refine_ls_number_parameters     268
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1112
_refine_ls_R_factor_gt           0.1045
_refine_ls_wR_factor_ref         0.3139
_refine_ls_wR_factor_gt          0.3093
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.111
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8151(4) 0.6145(14) 1.1016(4) 0.0367(14) Uani 1 1 d . . . . .
C1 C 0.8004(6) 0.702(2) 1.1883(5) 0.038(2) Uani 1 1 d . . . . .
H1 H 0.780556 0.893261 1.187086 0.045 Uiso 1 1 calc R U . . .
H2 H 0.859673 0.690663 1.222623 0.045 Uiso 1 1 calc R U . . .
C2 C 0.7265(6) 0.536(2) 1.2345(5) 0.037(2) Uani 1 1 d . . . . .
O2 O 0.6996(4) 0.3181(14) 1.2078(5) 0.0430(15) Uani 1 1 d . . . . .
O3 O 0.6962(4) 0.6489(14) 1.3102(4) 0.0399(15) Uani 1 1 d . . . . .
C3 C 0.6229(6) 0.498(2) 1.3551(6) 0.041(2) Uani 1 1 d . . . . .
H3 H 0.646149 0.317579 1.372496 0.049 Uiso 1 1 calc R U . . .
H4 H 0.568395 0.475007 1.314590 0.049 Uiso 1 1 calc R U . . .
C4 C 0.5956(7) 0.653(3) 1.4357(7) 0.054(3) Uani 1 1 d . . . . .
H5 H 0.579118 0.837294 1.418444 0.081 Uiso 1 1 calc R U . . .
H6 H 0.647915 0.656579 1.478388 0.081 Uiso 1 1 calc R U . . .
H7 H 0.541585 0.566116 1.463486 0.081 Uiso 1 1 calc R U . . .
C5 C 0.7421(5) 0.6229(18) 1.0409(5) 0.0299(16) Uani 1 1 d . . . . .
C6 C 0.6698(6) 0.8135(19) 1.0502(6) 0.0349(18) Uani 1 1 d . . . . .
H8 H 0.668975 0.931648 1.100166 0.042 Uiso 1 1 calc R U . . .
C7 C 0.6011(5) 0.8257(19) 0.9866(6) 0.0333(18) Uani 1 1 d . . . . .
H9 H 0.552400 0.954145 0.992635 0.040 Uiso 1 1 calc R U . . .
C8 C 0.6008(5) 0.6516(19) 0.9116(5) 0.0312(18) Uani 1 1 d . . . . .
C9 C 0.5269(5) 0.6617(19) 0.8482(5) 0.0335(19) Uani 1 1 d . . . . .
H10 H 0.478519 0.790567 0.855769 0.040 Uiso 1 1 calc R U . . .
C10 C 0.5229(5) 0.495(2) 0.7776(6) 0.0360(19) Uani 1 1 d . . . . .
H11 H 0.472681 0.505421 0.735829 0.043 Uiso 1 1 calc R U . . .
C11 C 0.5953(6) 0.302(2) 0.7667(6) 0.038(2) Uani 1 1 d . . . . .
H12 H 0.593176 0.183904 0.716833 0.045 Uiso 1 1 calc R U . . .
C12 C 0.6692(5) 0.2834(19) 0.8275(6) 0.0337(19) Uani 1 1 d . . . . .
H13 H 0.716756 0.152717 0.818727 0.040 Uiso 1 1 calc R U . . .
C13 C 0.6739(5) 0.4572(19) 0.9020(5) 0.0315(18) Uani 1 1 d . . . . .
C14 C 0.7460(5) 0.4442(19) 0.9696(5) 0.0317(18) Uani 1 1 d . . . . .
C15 C 0.8224(5) 0.2453(18) 0.9725(5) 0.0310(18) Uani 1 1 d . . . . .
H14 H 0.857482 0.230010 1.026462 0.037 Uiso 1 1 calc R U . . .
N1 N 0.8447(4) 0.0931(16) 0.9079(4) 0.0307(15) Uani 1 1 d . . . . .
N2 N 0.9181(4) -0.0802(16) 0.9290(5) 0.0317(15) Uani 1 1 d . . . . .
H15 H 0.938(7) -0.06(3) 0.985(7) 0.048 Uiso 1 1 d . U . . .
C16 C 0.9449(5) -0.2707(17) 0.8711(5) 0.0303(17) Uani 1 1 d . . . . .
O4 O 1.0090(3) -0.4272(13) 0.8915(4) 0.0328(13) Uani 1 1 d . . . . .
C17 C 0.8932(6) -0.2887(19) 0.7840(5) 0.0346(18) Uani 1 1 d . . . . .
H16 H 0.886360 -0.105213 0.758795 0.041 Uiso 1 1 calc R U . . .
H17 H 0.829741 -0.359867 0.795027 0.041 Uiso 1 1 calc R U . . .
C18 C 0.9413(5) -0.468(2) 0.7152(5) 0.0338(18) Uani 1 1 d . . . . .
H18 H 0.957662 -0.642126 0.743868 0.041 Uiso 1 1 calc R U . . .
H19 H 0.896580 -0.507010 0.665898 0.041 Uiso 1 1 calc R U . . .
C19 C 1.0297(5) -0.3455(19) 0.6758(6) 0.0348(18) Uani 1 1 d . . . . .
H20 H 1.016612 -0.156952 0.657998 0.042 Uiso 1 1 calc R U . . .
H21 H 1.079297 -0.342236 0.722320 0.042 Uiso 1 1 calc R U . . .
C20 C 1.0645(5) -0.498(2) 0.5958(5) 0.0343(18) Uani 1 1 d . . . . .
H22 H 1.013372 -0.508191 0.550869 0.041 Uiso 1 1 calc R U . . .
H23 H 1.079111 -0.685056 0.614666 0.041 Uiso 1 1 calc R U . . .
C21 C 1.1506(6) -0.379(2) 0.5513(5) 0.0377(19) Uani 1 1 d . . . . .
H24 H 1.139111 -0.186231 0.538942 0.045 Uiso 1 1 calc R U . . .
H25 H 1.204213 -0.391742 0.593357 0.045 Uiso 1 1 calc R U . . .
C22 C 1.1756(6) -0.516(2) 0.4663(6) 0.046(2) Uani 1 1 d . . . . .
H26 H 1.120528 -0.510571 0.425804 0.056 Uiso 1 1 calc R U . . .
H27 H 1.188721 -0.707958 0.479644 0.056 Uiso 1 1 calc R U . . .
C23 C 1.2595(6) -0.399(3) 0.4164(6) 0.048(2) Uani 1 1 d . . . . .
H28 H 1.315578 -0.413516 0.454149 0.073 Uiso 1 1 calc R U . . .
H29 H 1.247549 -0.209645 0.402203 0.073 Uiso 1 1 calc R U . . .
H30 H 1.268830 -0.500456 0.360915 0.073 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.379(9) . ?
O1 C1 1.385(10) . ?
C1 C2 1.514(12) . ?
C1 H1 0.9900 . ?
C1 H2 0.9900 . ?
C2 O2 1.212(12) . ?
C2 O3 1.341(11) . ?
O3 C3 1.458(10) . ?
C3 C4 1.485(14) . ?
C3 H3 0.9900 . ?
C3 H4 0.9900 . ?
C4 H5 0.9800 . ?
C4 H6 0.9800 . ?
C4 H7 0.9800 . ?
C5 C14 1.388(12) . ?
C5 C6 1.409(11) . ?
C6 C7 1.363(12) . ?
C6 H8 0.9500 . ?
C7 C8 1.416(12) . ?
C7 H9 0.9500 . ?
C8 C9 1.415(11) . ?
C8 C13 1.432(11) . ?
C9 C10 1.342(13) . ?
C9 H10 0.9500 . ?
C10 C11 1.420(12) . ?
C10 H11 0.9500 . ?
C11 C12 1.391(11) . ?
C11 H12 0.9500 . ?
C12 C13 1.411(12) . ?
C12 H13 0.9500 . ?
C13 C14 1.439(11) . ?
C14 C15 1.474(12) . ?
C15 N1 1.269(11) . ?
C15 H14 0.9500 . ?
N1 N2 1.392(10) . ?
N2 C16 1.341(11) . ?
N2 H15 0.89(11) . ?
C16 O4 1.238(10) . ?
C16 C17 1.494(11) . ?
C17 C18 1.531(11) . ?
C17 H16 0.9900 . ?
C17 H17 0.9900 . ?
C18 C19 1.528(11) . ?
C18 H18 0.9900 . ?
C18 H19 0.9900 . ?
C19 C20 1.505(11) . ?
C19 H20 0.9900 . ?
C19 H21 0.9900 . ?
C20 C21 1.526(11) . ?
C20 H22 0.9900 . ?
C20 H23 0.9900 . ?
C21 C22 1.488(13) . ?
C21 H24 0.9900 . ?
C21 H25 0.9900 . ?
C22 C23 1.534(13) . ?
C22 H26 0.9900 . ?
C22 H27 0.9900 . ?
C23 H28 0.9800 . ?
C23 H29 0.9800 . ?
C23 H30 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C1 119.1(6) . . ?
O1 C1 C2 111.6(7) . . ?
O1 C1 H1 109.3 . . ?
C2 C1 H1 109.3 . . ?
O1 C1 H2 109.3 . . ?
C2 C1 H2 109.3 . . ?
H1 C1 H2 108.0 . . ?
O2 C2 O3 123.2(9) . . ?
O2 C2 C1 123.9(8) . . ?
O3 C2 C1 112.9(8) . . ?
C2 O3 C3 114.5(7) . . ?
O3 C3 C4 107.8(8) . . ?
O3 C3 H3 110.1 . . ?
C4 C3 H3 110.1 . . ?
O3 C3 H4 110.1 . . ?
C4 C3 H4 110.1 . . ?
H3 C3 H4 108.5 . . ?
C3 C4 H5 109.5 . . ?
C3 C4 H6 109.5 . . ?
H5 C4 H6 109.5 . . ?
C3 C4 H7 109.5 . . ?
H5 C4 H7 109.5 . . ?
H6 C4 H7 109.5 . . ?
O1 C5 C14 116.8(7) . . ?
O1 C5 C6 120.4(7) . . ?
C14 C5 C6 122.7(7) . . ?
C7 C6 C5 119.0(8) . . ?
C7 C6 H8 120.5 . . ?
C5 C6 H8 120.5 . . ?
C6 C7 C8 121.6(8) . . ?
C6 C7 H9 119.2 . . ?
C8 C7 H9 119.2 . . ?
C9 C8 C7 120.4(7) . . ?
C9 C8 C13 120.0(7) . . ?
C7 C8 C13 119.6(7) . . ?
C10 C9 C8 122.1(8) . . ?
C10 C9 H10 119.0 . . ?
C8 C9 H10 119.0 . . ?
C9 C10 C11 118.7(7) . . ?
C9 C10 H11 120.6 . . ?
C11 C10 H11 120.6 . . ?
C12 C11 C10 121.4(8) . . ?
C12 C11 H12 119.3 . . ?
C10 C11 H12 119.3 . . ?
C11 C12 C13 120.3(8) . . ?
C11 C12 H13 119.8 . . ?
C13 C12 H13 119.8 . . ?
C12 C13 C8 117.5(7) . . ?
C12 C13 C14 123.8(8) . . ?
C8 C13 C14 118.7(7) . . ?
C5 C14 C13 118.5(7) . . ?
C5 C14 C15 116.2(7) . . ?
C13 C14 C15 125.3(8) . . ?
N1 C15 C14 124.6(7) . . ?
N1 C15 H14 117.7 . . ?
C14 C15 H14 117.7 . . ?
C15 N1 N2 112.9(7) . . ?
C16 N2 N1 120.6(7) . . ?
C16 N2 H15 127(8) . . ?
N1 N2 H15 112(8) . . ?
O4 C16 N2 119.9(7) . . ?
O4 C16 C17 122.5(8) . . ?
N2 C16 C17 117.6(7) . . ?
C16 C17 C18 113.5(7) . . ?
C16 C17 H16 108.9 . . ?
C18 C17 H16 108.9 . . ?
C16 C17 H17 108.9 . . ?
C18 C17 H17 108.9 . . ?
H16 C17 H17 107.7 . . ?
C19 C18 C17 113.9(7) . . ?
C19 C18 H18 108.8 . . ?
C17 C18 H18 108.8 . . ?
C19 C18 H19 108.8 . . ?
C17 C18 H19 108.8 . . ?
H18 C18 H19 107.7 . . ?
C20 C19 C18 112.7(7) . . ?
C20 C19 H20 109.0 . . ?
C18 C19 H20 109.0 . . ?
C20 C19 H21 109.0 . . ?
C18 C19 H21 109.0 . . ?
H20 C19 H21 107.8 . . ?
C19 C20 C21 115.3(8) . . ?
C19 C20 H22 108.5 . . ?
C21 C20 H22 108.5 . . ?
C19 C20 H23 108.5 . . ?
C21 C20 H23 108.5 . . ?
H22 C20 H23 107.5 . . ?
C22 C21 C20 113.5(8) . . ?
C22 C21 H24 108.9 . . ?
C20 C21 H24 108.9 . . ?
C22 C21 H25 108.9 . . ?
C20 C21 H25 108.9 . . ?
H24 C21 H25 107.7 . . ?
C21 C22 C23 116.1(9) . . ?
C21 C22 H26 108.3 . . ?
C23 C22 H26 108.3 . . ?
C21 C22 H27 108.3 . . ?
C23 C22 H27 108.3 . . ?
H26 C22 H27 107.4 . . ?
C22 C23 H28 109.5 . . ?
C22 C23 H29 109.5 . . ?
H28 C23 H29 109.5 . . ?
C22 C23 H30 109.5 . . ?
H28 C23 H30 109.5 . . ?
H29 C23 H30 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 O1 C1 C2 61.3(10) . . . . ?
O1 C1 C2 O2 16.0(12) . . . . ?
O1 C1 C2 O3 -166.4(7) . . . . ?
O2 C2 O3 C3 -4.2(12) . . . . ?
C1 C2 O3 C3 178.2(7) . . . . ?
C2 O3 C3 C4 -178.5(8) . . . . ?
C1 O1 C5 C14 -155.1(8) . . . . ?
C1 O1 C5 C6 27.4(11) . . . . ?
O1 C5 C6 C7 176.7(8) . . . . ?
C14 C5 C6 C7 -0.6(12) . . . . ?
C5 C6 C7 C8 0.1(13) . . . . ?
C6 C7 C8 C9 177.7(8) . . . . ?
C6 C7 C8 C13 0.1(12) . . . . ?
C7 C8 C9 C10 -178.2(8) . . . . ?
C13 C8 C9 C10 -0.6(13) . . . . ?
C8 C9 C10 C11 0.1(14) . . . . ?
C9 C10 C11 C12 0.2(14) . . . . ?
C10 C11 C12 C13 -0.1(13) . . . . ?
C11 C12 C13 C8 -0.4(12) . . . . ?
C11 C12 C13 C14 177.6(8) . . . . ?
C9 C8 C13 C12 0.8(11) . . . . ?
C7 C8 C13 C12 178.4(8) . . . . ?
C9 C8 C13 C14 -177.4(8) . . . . ?
C7 C8 C13 C14 0.2(11) . . . . ?
O1 C5 C14 C13 -176.5(7) . . . . ?
C6 C5 C14 C13 0.9(12) . . . . ?
O1 C5 C14 C15 6.5(11) . . . . ?
C6 C5 C14 C15 -176.0(7) . . . . ?
C12 C13 C14 C5 -178.7(8) . . . . ?
C8 C13 C14 C5 -0.7(11) . . . . ?
C12 C13 C14 C15 -2.1(12) . . . . ?
C8 C13 C14 C15 176.0(7) . . . . ?
C5 C14 C15 N1 -169.5(8) . . . . ?
C13 C14 C15 N1 13.7(13) . . . . ?
C14 C15 N1 N2 -178.6(7) . . . . ?
C15 N1 N2 C16 174.1(7) . . . . ?
N1 N2 C16 O4 -178.4(7) . . . . ?
N1 N2 C16 C17 0.0(11) . . . . ?
O4 C16 C17 C18 -13.9(12) . . . . ?
N2 C16 C17 C18 167.7(7) . . . . ?
C16 C17 C18 C19 -72.3(10) . . . . ?
C17 C18 C19 C20 -168.4(7) . . . . ?
C18 C19 C20 C21 177.8(7) . . . . ?
C19 C20 C21 C22 -172.8(8) . . . . ?
C20 C21 C22 C23 177.8(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1 O2 0.99 2.43 3.394(12) 165.2 1_565 yes
C6 H8 O2 0.95 2.54 3.463(11) 164.0 1_565 yes
C15 H14 O4 0.95 2.39 3.256(10) 151.1 2_757 yes
N2 H15 O4 0.89(11) 2.10(12) 2.969(9) 167(12) 2_757 yes

_refine_diff_density_max         0.741
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.124



_exptl_crystal_recrystallization_method 'From the Melt'
_exptl_crystal_preparation       photochromic
####################################################################### 
# 
# 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_E-d7-A
_database_code_depnum_ccdc_archive 'CCDC 2431295'
loop_
_audit_author_name
_audit_author_address
'Isao Yoshikawa'
;Institute of Industrial Science, The University of Tokyo
Japan
;
_audit_update_record             
;
2025-03-14 deposited with the CCDC.	2025-07-08 downloaded from the CCDC.
;

_vrf_PLAT082_E-d7-A              
;
PROBLEM: High R1 Value .................................. 0.26 Report
RESPONSE: Quality of the crystals were low.
;
_vrf_PLAT084_E-d7-A              
;
PROBLEM: High wR2 Value (i.e. > 0.25) ................... 0.63 Report
RESPONSE: Quality of the crystals were low.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H30 N2 O4'
_chemical_formula_sum            'C23 H30 N2 O4'
_chemical_formula_weight         398.49

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   27.00(2)
_cell_length_b                   4.853(2)
_cell_length_c                   15.832(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.16(8)
_cell_angle_gamma                90
_cell_volume                     2062(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1366
_cell_measurement_theta_min      3.3160
_cell_measurement_theta_max      70.8260

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.040
_shelx_estimated_absorpt_T_min   0.785
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_coefficient_mu    0.704
_exptl_absorpt_correction_T_min  0.628
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            11390
_diffrn_reflns_av_unetI/netI     0.2077
_diffrn_reflns_av_R_equivalents  0.2190
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.807
_diffrn_reflns_theta_max         77.878
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4033
_reflns_number_gt                2106
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'CrysAlisPro 1.171.41.107a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_refine_special_details          'Refined as a 2-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4033
_refine_ls_number_parameters     250
_refine_ls_number_restraints     162
_refine_ls_R_factor_all          0.3395
_refine_ls_R_factor_gt           0.2653
_refine_ls_wR_factor_ref         0.6375
_refine_ls_wR_factor_gt          0.5526
_refine_ls_goodness_of_fit_ref   1.933
_refine_ls_restrained_S_all      1.899
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1468(4) 0.3199(18) 0.3372(6) 0.048(3) Uani 1 1 d . . . . .
C1 C 0.1063(7) 0.128(3) 0.3323(11) 0.063(5) Uani 1 1 d . . . . .
H1 H 0.074430 0.226390 0.335368 0.075 Uiso 1 1 calc R U . . .
H2 H 0.111006 -0.004047 0.380236 0.075 Uiso 1 1 calc R U . . .
C2 C 0.1052(6) -0.019(3) 0.2516(11) 0.054(4) Uani 1 1 d . . . . .
H3 H 0.086355 -0.193634 0.254204 0.065 Uiso 1 1 calc R U . . .
H4 H 0.139565 -0.064603 0.239774 0.065 Uiso 1 1 calc R U . . .
O2 O 0.0813(4) 0.157(3) 0.1844(8) 0.071(4) Uani 1 1 d . . . . .
C3 C 0.0300(7) 0.115(4) 0.1671(15) 0.079(6) Uani 1 1 d . . . . .
O3 O 0.0070(6) -0.058(3) 0.1890(17) 0.145(9) Uani 1 1 d . . . . .
C4 C 0.0159(6) 0.310(4) 0.0957(13) 0.071(5) Uani 1 1 d . . . . .
H5 H -0.003831 0.211512 0.049492 0.107 Uiso 1 1 calc R U . . .
H6 H 0.046064 0.384023 0.074910 0.107 Uiso 1 1 calc R U . . .
H7 H -0.003902 0.460785 0.115647 0.107 Uiso 1 1 calc R U . . .
C5 C 0.1519(6) 0.480(2) 0.4075(8) 0.040(3) Uani 1 1 d . . . . .
C6 C 0.1209(7) 0.512(3) 0.4658(9) 0.051(3) Uani 1 1 d . . . . .
H8 H 0.091930 0.399961 0.461521 0.061 Uiso 1 1 calc R U . . .
C7 C 0.1273(6) 0.695(3) 0.5321(9) 0.046(3) Uani 1 1 d . . . . .
H9 H 0.102317 0.716251 0.569575 0.055 Uiso 1 1 calc R U . . .
C8 C 0.1723(6) 0.855(3) 0.5440(8) 0.043(3) Uani 1 1 d . . . . .
C9 C 0.1801(6) 1.038(3) 0.6125(9) 0.046(3) Uani 1 1 d . . . . .
H10 H 0.155997 1.056283 0.651794 0.055 Uiso 1 1 calc R U . . .
C10 C 0.2237(6) 1.195(3) 0.6220(9) 0.048(3) Uani 1 1 d . . . . .
H11 H 0.229436 1.320790 0.667865 0.058 Uiso 1 1 calc R U . . .
C11 C 0.2589(6) 1.166(2) 0.5643(9) 0.047(3) Uani 1 1 d . . . . .
H12 H 0.288466 1.274073 0.572378 0.057 Uiso 1 1 calc R U . . .
C12 C 0.2526(5) 0.986(2) 0.4949(8) 0.037(3) Uani 1 1 d . . . . .
H13 H 0.277269 0.967040 0.456729 0.044 Uiso 1 1 calc R U . . .
C13 C 0.2070(5) 0.830(2) 0.4843(8) 0.038(3) Uani 1 1 d . . . . .
C14 C 0.1999(5) 0.642(2) 0.4142(7) 0.035(2) Uani 1 1 d . . . . .
C15 C 0.2349(5) 0.578(2) 0.3535(8) 0.040(3) Uani 1 1 d . . . . .
H14 H 0.238331 0.392976 0.335250 0.048 Uiso 1 1 calc R U . . .
N1 N 0.2612(5) 0.769(2) 0.3244(6) 0.040(3) Uani 1 1 d . . . . .
N2 N 0.2944(4) 0.677(2) 0.2727(7) 0.039(2) Uani 1 1 d . . . . .
H15 H 0.297512 0.498835 0.264154 0.047 Uiso 1 1 calc R U . . .
C16 C 0.3233(5) 0.859(2) 0.2334(8) 0.037(3) Uani 1 1 d . . . . .
O4 O 0.3227(3) 1.1127(18) 0.2459(5) 0.034(2) Uiso 1 1 d . . . . .
C17 C 0.3599(4) 0.741(3) 0.1772(8) 0.031(3) Uiso 1 1 d . . . . .
H16 H 0.362373 0.539978 0.187243 0.037 Uiso 1 1 calc R U . . .
H17 H 0.346420 0.768973 0.117212 0.037 Uiso 1 1 calc R U . . .
C18 C 0.4116(6) 0.861(2) 0.1897(7) 0.039(3) Uani 1 1 d . . . . .
H18 H 0.409192 1.062279 0.180653 0.047 Uiso 1 1 calc R U . . .
H19 H 0.425434 0.829812 0.249445 0.047 Uiso 1 1 calc R U . . .
C19 C 0.4473(5) 0.747(2) 0.1332(7) 0.035(3) Uani 1 1 d . . . . .
H20 H 0.433303 0.775195 0.073421 0.042 Uiso 1 1 calc R U . . .
H21 H 0.450238 0.545820 0.142943 0.042 Uiso 1 1 calc R U . . .
C20 C 0.4991(5) 0.874(3) 0.1458(8) 0.034(3) Uiso 1 1 d . . . . .
H22 H 0.495878 1.074612 0.136258 0.041 Uiso 1 1 calc R U . . .
H23 H 0.512784 0.845623 0.205709 0.041 Uiso 1 1 calc R U . . .
C21 C 0.5358(5) 0.766(3) 0.0906(10) 0.043(3) Uani 1 1 d . . . . .
H24 H 0.521842 0.790451 0.030707 0.052 Uiso 1 1 calc R U . . .
H25 H 0.539431 0.565060 0.100859 0.052 Uiso 1 1 calc R U . . .
C22 C 0.5867(6) 0.891(3) 0.1013(8) 0.042(3) Uani 1 1 d . . . . .
H26 H 0.583260 1.091245 0.089505 0.050 Uiso 1 1 calc R U . . .
H27 H 0.600408 0.871092 0.161532 0.050 Uiso 1 1 calc R U . . .
C23 C 0.6240(6) 0.777(3) 0.0472(9) 0.044(3) Uani 1 1 d . . . . .
H28 H 0.631530 0.585830 0.063450 0.066 Uiso 1 1 calc R U . . .
H29 H 0.654637 0.887109 0.055303 0.066 Uiso 1 1 calc R U . . .
H30 H 0.610326 0.784448 -0.012664 0.066 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.351(15) . ?
O1 C1 1.433(18) . ?
C1 C2 1.46(2) . ?
C1 H1 0.9900 . ?
C1 H2 0.9900 . ?
C2 O2 1.462(18) . ?
C2 H3 0.9900 . ?
C2 H4 0.9900 . ?
O2 C3 1.40(2) . ?
C3 O3 1.12(3) . ?
C3 C4 1.49(3) . ?
C4 H5 0.9800 . ?
C4 H6 0.9800 . ?
C4 H7 0.9800 . ?
C5 C6 1.32(2) . ?
C5 C14 1.511(19) . ?
C6 C7 1.37(2) . ?
C6 H8 0.9500 . ?
C7 C8 1.44(2) . ?
C7 H9 0.9500 . ?
C8 C9 1.403(18) . ?
C8 C13 1.40(2) . ?
C9 C10 1.40(2) . ?
C9 H10 0.9500 . ?
C10 C11 1.39(2) . ?
C10 H11 0.9500 . ?
C11 C12 1.401(16) . ?
C11 H12 0.9500 . ?
C12 C13 1.439(19) . ?
C12 H13 0.9500 . ?
C13 C14 1.434(16) . ?
C14 C15 1.45(2) . ?
C15 N1 1.283(17) . ?
C15 H14 0.9500 . ?
N1 N2 1.352(17) . ?
N2 C16 1.370(17) . ?
N2 H15 0.8800 . ?
C16 O4 1.248(15) . ?
C16 C17 1.51(2) . ?
C17 C18 1.504(18) . ?
C17 H16 0.9900 . ?
C17 H17 0.9900 . ?
C18 C19 1.49(2) . ?
C18 H18 0.9900 . ?
C18 H19 0.9900 . ?
C19 C20 1.523(18) . ?
C19 H20 0.9900 . ?
C19 H21 0.9900 . ?
C20 C21 1.48(2) . ?
C20 H22 0.9900 . ?
C20 H23 0.9900 . ?
C21 C22 1.50(2) . ?
C21 H24 0.9900 . ?
C21 H25 0.9900 . ?
C22 C23 1.50(2) . ?
C22 H26 0.9900 . ?
C22 H27 0.9900 . ?
C23 H28 0.9800 . ?
C23 H29 0.9800 . ?
C23 H30 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C1 115.4(14) . . ?
O1 C1 C2 108.0(16) . . ?
O1 C1 H1 110.1 . . ?
C2 C1 H1 110.1 . . ?
O1 C1 H2 110.1 . . ?
C2 C1 H2 110.1 . . ?
H1 C1 H2 108.4 . . ?
C1 C2 O2 108.4(12) . . ?
C1 C2 H3 110.0 . . ?
O2 C2 H3 110.0 . . ?
C1 C2 H4 110.0 . . ?
O2 C2 H4 110.0 . . ?
H3 C2 H4 108.4 . . ?
C3 O2 C2 114.1(15) . . ?
O3 C3 O2 128.2(18) . . ?
O3 C3 C4 127.1(17) . . ?
O2 C3 C4 102.9(18) . . ?
C3 C4 H5 109.5 . . ?
C3 C4 H6 109.5 . . ?
H5 C4 H6 109.5 . . ?
C3 C4 H7 109.5 . . ?
H5 C4 H7 109.5 . . ?
H6 C4 H7 109.5 . . ?
C6 C5 O1 128.9(14) . . ?
C6 C5 C14 119.4(12) . . ?
O1 C5 C14 111.7(14) . . ?
C5 C6 C7 125.2(15) . . ?
C5 C6 H8 117.4 . . ?
C7 C6 H8 117.4 . . ?
C6 C7 C8 118.9(16) . . ?
C6 C7 H9 120.5 . . ?
C8 C7 H9 120.5 . . ?
C9 C8 C13 121.3(14) . . ?
C9 C8 C7 119.8(15) . . ?
C13 C8 C7 118.9(12) . . ?
C10 C9 C8 118.8(16) . . ?
C10 C9 H10 120.6 . . ?
C8 C9 H10 120.6 . . ?
C11 C10 C9 120.3(13) . . ?
C11 C10 H11 119.9 . . ?
C9 C10 H11 119.9 . . ?
C10 C11 C12 122.7(14) . . ?
C10 C11 H12 118.6 . . ?
C12 C11 H12 118.6 . . ?
C11 C12 C13 116.8(15) . . ?
C11 C12 H13 121.6 . . ?
C13 C12 H13 121.6 . . ?
C8 C13 C14 122.0(13) . . ?
C8 C13 C12 120.1(11) . . ?
C14 C13 C12 117.8(14) . . ?
C13 C14 C15 127.3(13) . . ?
C13 C14 C5 115.5(13) . . ?
C15 C14 C5 117.1(10) . . ?
N1 C15 C14 120.5(12) . . ?
N1 C15 H14 119.7 . . ?
C14 C15 H14 119.7 . . ?
C15 N1 N2 114.2(11) . . ?
N1 N2 C16 120.6(10) . . ?
N1 N2 H15 119.7 . . ?
C16 N2 H15 119.7 . . ?
O4 C16 N2 123.1(13) . . ?
O4 C16 C17 119.2(12) . . ?
N2 C16 C17 117.6(11) . . ?
C18 C17 C16 115.7(10) . . ?
C18 C17 H16 108.4 . . ?
C16 C17 H16 108.4 . . ?
C18 C17 H17 108.4 . . ?
C16 C17 H17 108.4 . . ?
H16 C17 H17 107.4 . . ?
C19 C18 C17 115.3(10) . . ?
C19 C18 H18 108.4 . . ?
C17 C18 H18 108.4 . . ?
C19 C18 H19 108.4 . . ?
C17 C18 H19 108.4 . . ?
H18 C18 H19 107.5 . . ?
C18 C19 C20 114.6(10) . . ?
C18 C19 H20 108.6 . . ?
C20 C19 H20 108.6 . . ?
C18 C19 H21 108.6 . . ?
C20 C19 H21 108.6 . . ?
H20 C19 H21 107.6 . . ?
C21 C20 C19 116.3(11) . . ?
C21 C20 H22 108.2 . . ?
C19 C20 H22 108.2 . . ?
C21 C20 H23 108.2 . . ?
C19 C20 H23 108.2 . . ?
H22 C20 H23 107.4 . . ?
C20 C21 C22 116.9(12) . . ?
C20 C21 H24 108.1 . . ?
C22 C21 H24 108.1 . . ?
C20 C21 H25 108.1 . . ?
C22 C21 H25 108.1 . . ?
H24 C21 H25 107.3 . . ?
C23 C22 C21 116.8(11) . . ?
C23 C22 H26 108.1 . . ?
C21 C22 H26 108.1 . . ?
C23 C22 H27 108.1 . . ?
C21 C22 H27 108.1 . . ?
H26 C22 H27 107.3 . . ?
C22 C23 H28 109.5 . . ?
C22 C23 H29 109.5 . . ?
H28 C23 H29 109.5 . . ?
C22 C23 H30 109.5 . . ?
H28 C23 H30 109.5 . . ?
H29 C23 H30 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 O1 C1 C2 178.0(10) . . . . ?
O1 C1 C2 O2 -79.5(15) . . . . ?
C1 C2 O2 C3 -92.7(17) . . . . ?
C2 O2 C3 O3 -12(4) . . . . ?
C2 O2 C3 C4 -177.9(13) . . . . ?
C1 O1 C5 C6 -11.0(18) . . . . ?
C1 O1 C5 C14 170.8(10) . . . . ?
O1 C5 C6 C7 -174.7(12) . . . . ?
C14 C5 C6 C7 3(2) . . . . ?
C5 C6 C7 C8 -4(2) . . . . ?
C6 C7 C8 C9 -178.6(12) . . . . ?
C6 C7 C8 C13 3.9(17) . . . . ?
C13 C8 C9 C10 -1.4(17) . . . . ?
C7 C8 C9 C10 -178.9(11) . . . . ?
C8 C9 C10 C11 -0.3(17) . . . . ?
C9 C10 C11 C12 0.5(18) . . . . ?
C10 C11 C12 C13 1.0(17) . . . . ?
C9 C8 C13 C14 179.5(11) . . . . ?
C7 C8 C13 C14 -3.0(16) . . . . ?
C9 C8 C13 C12 3.0(17) . . . . ?
C7 C8 C13 C12 -179.5(11) . . . . ?
C11 C12 C13 C8 -2.7(16) . . . . ?
C11 C12 C13 C14 -179.4(10) . . . . ?
C8 C13 C14 C15 -173.4(11) . . . . ?
C12 C13 C14 C15 3.2(16) . . . . ?
C8 C13 C14 C5 2.0(15) . . . . ?
C12 C13 C14 C5 178.6(10) . . . . ?
C6 C5 C14 C13 -2.0(15) . . . . ?
O1 C5 C14 C13 176.3(9) . . . . ?
C6 C5 C14 C15 173.8(11) . . . . ?
O1 C5 C14 C15 -7.8(13) . . . . ?
C13 C14 C15 N1 -40.2(17) . . . . ?
C5 C14 C15 N1 144.5(11) . . . . ?
C14 C15 N1 N2 176.0(10) . . . . ?
C15 N1 N2 C16 176.6(11) . . . . ?
N1 N2 C16 O4 3.8(17) . . . . ?
N1 N2 C16 C17 179.3(9) . . . . ?
O4 C16 C17 C18 41.9(15) . . . . ?
N2 C16 C17 C18 -133.8(11) . . . . ?
C16 C17 C18 C19 -179.0(9) . . . . ?
C17 C18 C19 C20 179.1(10) . . . . ?
C18 C19 C20 C21 180.0(10) . . . . ?
C19 C20 C21 C22 179.0(10) . . . . ?
C20 C21 C22 C23 178.5(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1 O3 0.99 2.43 3.40(2) 167.7 2 yes
C4 H7 O3 0.98 2.61 3.43(3) 140.7 1_565 yes
N2 H15 O4 0.88 2.02 2.886(14) 165.9 1_545 yes
C17 H16 O4 0.99 2.55 3.425(15) 146.7 1_545 yes

_refine_diff_density_max         1.003
_refine_diff_density_min         -0.985
_refine_diff_density_rms         0.239



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
_exptl_crystal_preparation       photochromic
####################################################################### 
# 
# 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_E-c7-S
_database_code_depnum_ccdc_archive 'CCDC 2431297'
loop_
_audit_author_name
_audit_author_address
'Isao Yoshikawa'
;Institute of Industrial Science, The University of Tokyo
Japan
;
_audit_update_record             
;
2025-03-14 deposited with the CCDC.	2025-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H32 N2 O3'
_chemical_formula_sum            'C23 H32 N2 O3'
_chemical_formula_weight         384.50

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.8189(8)
_cell_length_b                   6.0464(5)
_cell_length_c                   33.609(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.370(7)
_cell_angle_gamma                90
_cell_volume                     2175.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2797
_cell_measurement_theta_min      2.7020
_cell_measurement_theta_max      70.7370

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.615
_shelx_estimated_absorpt_T_min   0.887
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_T_min  0.45338
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            8960
_diffrn_reflns_av_unetI/netI     0.0947
_diffrn_reflns_av_R_equivalents  0.0793
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         4.576
_diffrn_reflns_theta_max         71.720
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             4054
_reflns_number_gt                3206
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.41.107a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1740P)²+16.8536P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4054
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1574
_refine_ls_R_factor_gt           0.1449
_refine_ls_wR_factor_ref         0.4199
_refine_ls_wR_factor_gt          0.4123
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2622(3) 0.0776(7) 0.27670(12) 0.0298(10) Uani 1 1 d . . . . .
C1 C 0.2582(5) -0.0941(11) 0.30595(18) 0.0306(13) Uani 1 1 d . . . . .
H1 H 0.272802 -0.239753 0.294005 0.037 Uiso 1 1 calc R U . . .
H2 H 0.175299 -0.096837 0.315097 0.037 Uiso 1 1 calc R U . . .
C2 C 0.3584(5) -0.0477(11) 0.34089(18) 0.0334(14) Uani 1 1 d . . . . .
H3 H 0.371033 -0.180036 0.358338 0.040 Uiso 1 1 calc R U . . .
H4 H 0.438047 -0.015585 0.330784 0.040 Uiso 1 1 calc R U . . .
O2 O 0.3255(4) 0.1343(8) 0.36360(12) 0.0348(11) Uani 1 1 d . . . . .
C3 C 0.4092(6) 0.1585(12) 0.40011(18) 0.0373(15) Uani 1 1 d . . . . .
H5 H 0.494853 0.185360 0.394077 0.045 Uiso 1 1 calc R U . . .
H6 H 0.410263 0.020875 0.416117 0.045 Uiso 1 1 calc R U . . .
C4 C 0.3687(6) 0.3482(13) 0.4237(2) 0.0433(16) Uani 1 1 d . . . . .
H7 H 0.367295 0.483808 0.407659 0.065 Uiso 1 1 calc R U . . .
H8 H 0.427439 0.366020 0.448574 0.065 Uiso 1 1 calc R U . . .
H9 H 0.284926 0.318958 0.430249 0.065 Uiso 1 1 calc R U . . .
C5 C 0.1740(5) 0.0707(10) 0.24261(17) 0.0262(12) Uani 1 1 d . . . . .
C6 C 0.0868(5) -0.1029(11) 0.23598(18) 0.0303(13) Uani 1 1 d . . . . .
H10 H 0.086557 -0.217941 0.255211 0.036 Uiso 1 1 calc R U . . .
C7 C 0.0020(5) -0.1037(11) 0.20126(18) 0.0306(13) Uani 1 1 d . . . . .
H11 H -0.055898 -0.222115 0.196246 0.037 Uiso 1 1 calc R U . . .
C8 C 0.0000(5) 0.0687(11) 0.17314(17) 0.0297(13) Uani 1 1 d . . . . .
C9 C -0.0903(5) 0.0634(11) 0.13745(18) 0.0331(14) Uani 1 1 d . . . . .
H12 H -0.146382 -0.057867 0.132772 0.040 Uiso 1 1 calc R U . . .
C10 C -0.0961(5) 0.2296(12) 0.11045(18) 0.0348(14) Uani 1 1 d . . . . .
H13 H -0.155423 0.223526 0.086670 0.042 Uiso 1 1 calc R U . . .
C11 C -0.0151(5) 0.4115(11) 0.11730(18) 0.0338(14) Uani 1 1 d . . . . .
H14 H -0.021704 0.530102 0.098575 0.041 Uiso 1 1 calc R U . . .
C12 C 0.0743(5) 0.4187(11) 0.15120(17) 0.0302(13) Uani 1 1 d . . . . .
H15 H 0.129473 0.541556 0.155214 0.036 Uiso 1 1 calc R U . . .
C13 C 0.0852(5) 0.2467(10) 0.17994(17) 0.0271(12) Uani 1 1 d . . . . .
C14 C 0.1773(5) 0.2422(10) 0.21601(16) 0.0252(12) Uani 1 1 d . . . . .
C15 C 0.2731(5) 0.4121(10) 0.22649(17) 0.0258(12) Uani 1 1 d . . . . .
H16 H 0.320084 0.408928 0.252674 0.031 Uiso 1 1 calc R U . . .
N1 N 0.2970(4) 0.5638(9) 0.20243(14) 0.0286(11) Uani 1 1 d . . . . .
N2 N 0.3891(4) 0.7122(8) 0.21683(14) 0.0271(11) Uani 1 1 d . . . . .
H17 H 0.435117 0.691405 0.240358 0.032 Uiso 1 1 calc R U . . .
C16 C 0.4077(5) 0.8903(10) 0.19425(17) 0.0258(12) Uani 1 1 d . . . . .
O3 O 0.4861(3) 1.0316(7) 0.20641(12) 0.0310(10) Uani 1 1 d . . . . .
C17 C 0.3253(5) 0.9062(10) 0.15410(17) 0.0279(12) Uani 1 1 d . . . . .
H18 H 0.337392 0.771541 0.138342 0.034 Uiso 1 1 calc R U . . .
H19 H 0.237016 0.908903 0.158680 0.034 Uiso 1 1 calc R U . . .
C18 C 0.3494(5) 1.1060(11) 0.12955(17) 0.0318(13) Uani 1 1 d . . . . .
H20 H 0.437579 1.104434 0.124759 0.038 Uiso 1 1 calc R U . . .
H21 H 0.336296 1.241552 0.144907 0.038 Uiso 1 1 calc R U . . .
C19 C 0.2640(5) 1.1121(11) 0.08919(18) 0.0334(14) Uani 1 1 d . . . . .
H22 H 0.284798 0.986041 0.072579 0.040 Uiso 1 1 calc R U . . .
H23 H 0.176398 1.093533 0.093928 0.040 Uiso 1 1 calc R U . . .
C20 C 0.2746(6) 1.3242(11) 0.06616(18) 0.0353(14) Uani 1 1 d . . . . .
H24 H 0.362662 1.344570 0.062097 0.042 Uiso 1 1 calc R U . . .
H25 H 0.251853 1.449799 0.082563 0.042 Uiso 1 1 calc R U . . .
C21 C 0.1925(7) 1.3304(13) 0.0255(2) 0.0445(17) Uani 1 1 d . . . . .
H26 H 0.107302 1.281425 0.028931 0.053 Uiso 1 1 calc R U . . .
H27 H 0.225604 1.223763 0.007378 0.053 Uiso 1 1 calc R U . . .
C22 C 0.1838(8) 1.5580(15) 0.0056(2) 0.055(2) Uani 1 1 d . . . . .
H28 H 0.128538 1.547337 -0.020533 0.066 Uiso 1 1 calc R U . . .
H29 H 0.144463 1.661967 0.022759 0.066 Uiso 1 1 calc R U . . .
C23 C 0.3087(8) 1.6523(15) -0.0015(2) 0.054(2) Uani 1 1 d . . . . .
H30 H 0.359955 1.683287 0.024411 0.081 Uiso 1 1 calc R U . . .
H31 H 0.295094 1.789468 -0.017043 0.081 Uiso 1 1 calc R U . . .
H32 H 0.351844 1.544876 -0.016473 0.081 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.381(6) . ?
O1 C1 1.435(7) . ?
C1 C2 1.504(8) . ?
C1 H1 0.9900 . ?
C1 H2 0.9900 . ?
C2 O2 1.414(8) . ?
C2 H3 0.9900 . ?
C2 H4 0.9900 . ?
O2 C3 1.423(7) . ?
C3 C4 1.495(10) . ?
C3 H5 0.9900 . ?
C3 H6 0.9900 . ?
C4 H7 0.9800 . ?
C4 H8 0.9800 . ?
C4 H9 0.9800 . ?
C5 C14 1.373(8) . ?
C5 C6 1.407(8) . ?
C6 C7 1.375(8) . ?
C6 H10 0.9500 . ?
C7 C8 1.405(9) . ?
C7 H11 0.9500 . ?
C8 C13 1.413(8) . ?
C8 C9 1.433(8) . ?
C9 C10 1.349(9) . ?
C9 H12 0.9500 . ?
C10 C11 1.404(9) . ?
C10 H13 0.9500 . ?
C11 C12 1.384(8) . ?
C11 H14 0.9500 . ?
C12 C13 1.413(9) . ?
C12 H15 0.9500 . ?
C13 C14 1.453(7) . ?
C14 C15 1.466(8) . ?
C15 N1 1.274(8) . ?
C15 H16 0.9500 . ?
N1 N2 1.376(6) . ?
N2 C16 1.349(8) . ?
N2 H17 0.8800 . ?
C16 O3 1.231(7) . ?
C16 C17 1.508(7) . ?
C17 C18 1.507(9) . ?
C17 H18 0.9900 . ?
C17 H19 0.9900 . ?
C18 C19 1.527(8) . ?
C18 H20 0.9900 . ?
C18 H21 0.9900 . ?
C19 C20 1.511(9) . ?
C19 H22 0.9900 . ?
C19 H23 0.9900 . ?
C20 C21 1.517(8) . ?
C20 H24 0.9900 . ?
C20 H25 0.9900 . ?
C21 C22 1.527(11) . ?
C21 H26 0.9900 . ?
C21 H27 0.9900 . ?
C22 C23 1.518(11) . ?
C22 H28 0.9900 . ?
C22 H29 0.9900 . ?
C23 H30 0.9800 . ?
C23 H31 0.9800 . ?
C23 H32 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C1 117.5(4) . . ?
O1 C1 C2 108.1(5) . . ?
O1 C1 H1 110.1 . . ?
C2 C1 H1 110.1 . . ?
O1 C1 H2 110.1 . . ?
C2 C1 H2 110.1 . . ?
H1 C1 H2 108.4 . . ?
O2 C2 C1 110.9(5) . . ?
O2 C2 H3 109.5 . . ?
C1 C2 H3 109.5 . . ?
O2 C2 H4 109.5 . . ?
C1 C2 H4 109.5 . . ?
H3 C2 H4 108.0 . . ?
C2 O2 C3 111.5(4) . . ?
O2 C3 C4 109.7(5) . . ?
O2 C3 H5 109.7 . . ?
C4 C3 H5 109.7 . . ?
O2 C3 H6 109.7 . . ?
C4 C3 H6 109.7 . . ?
H5 C3 H6 108.2 . . ?
C3 C4 H7 109.5 . . ?
C3 C4 H8 109.5 . . ?
H7 C4 H8 109.5 . . ?
C3 C4 H9 109.5 . . ?
H7 C4 H9 109.5 . . ?
H8 C4 H9 109.5 . . ?
C14 C5 O1 115.9(5) . . ?
C14 C5 C6 122.7(5) . . ?
O1 C5 C6 121.3(5) . . ?
C7 C6 C5 119.1(6) . . ?
C7 C6 H10 120.5 . . ?
C5 C6 H10 120.5 . . ?
C6 C7 C8 120.7(5) . . ?
C6 C7 H11 119.6 . . ?
C8 C7 H11 119.6 . . ?
C7 C8 C13 120.7(5) . . ?
C7 C8 C9 119.2(5) . . ?
C13 C8 C9 120.1(6) . . ?
C10 C9 C8 120.4(6) . . ?
C10 C9 H12 119.8 . . ?
C8 C9 H12 119.8 . . ?
C9 C10 C11 120.4(5) . . ?
C9 C10 H13 119.8 . . ?
C11 C10 H13 119.8 . . ?
C12 C11 C10 120.3(6) . . ?
C12 C11 H14 119.9 . . ?
C10 C11 H14 119.9 . . ?
C11 C12 C13 121.2(6) . . ?
C11 C12 H15 119.4 . . ?
C13 C12 H15 119.4 . . ?
C12 C13 C8 117.6(5) . . ?
C12 C13 C14 124.2(5) . . ?
C8 C13 C14 118.2(5) . . ?
C5 C14 C13 118.5(5) . . ?
C5 C14 C15 117.2(5) . . ?
C13 C14 C15 124.2(5) . . ?
N1 C15 C14 123.6(5) . . ?
N1 C15 H16 118.2 . . ?
C14 C15 H16 118.2 . . ?
C15 N1 N2 116.7(5) . . ?
C16 N2 N1 118.8(5) . . ?
C16 N2 H17 120.6 . . ?
N1 N2 H17 120.6 . . ?
O3 C16 N2 121.3(5) . . ?
O3 C16 C17 122.8(5) . . ?
N2 C16 C17 115.9(5) . . ?
C18 C17 C16 114.5(5) . . ?
C18 C17 H18 108.6 . . ?
C16 C17 H18 108.6 . . ?
C18 C17 H19 108.6 . . ?
C16 C17 H19 108.6 . . ?
H18 C17 H19 107.6 . . ?
C17 C18 C19 112.1(5) . . ?
C17 C18 H20 109.2 . . ?
C19 C18 H20 109.2 . . ?
C17 C18 H21 109.2 . . ?
C19 C18 H21 109.2 . . ?
H20 C18 H21 107.9 . . ?
C20 C19 C18 113.2(5) . . ?
C20 C19 H22 108.9 . . ?
C18 C19 H22 108.9 . . ?
C20 C19 H23 108.9 . . ?
C18 C19 H23 108.9 . . ?
H22 C19 H23 107.7 . . ?
C19 C20 C21 113.8(5) . . ?
C19 C20 H24 108.8 . . ?
C21 C20 H24 108.8 . . ?
C19 C20 H25 108.8 . . ?
C21 C20 H25 108.8 . . ?
H24 C20 H25 107.7 . . ?
C20 C21 C22 114.0(6) . . ?
C20 C21 H26 108.7 . . ?
C22 C21 H26 108.7 . . ?
C20 C21 H27 108.7 . . ?
C22 C21 H27 108.7 . . ?
H26 C21 H27 107.6 . . ?
C23 C22 C21 114.1(7) . . ?
C23 C22 H28 108.7 . . ?
C21 C22 H28 108.7 . . ?
C23 C22 H29 108.7 . . ?
C21 C22 H29 108.7 . . ?
H28 C22 H29 107.6 . . ?
C22 C23 H30 109.5 . . ?
C22 C23 H31 109.5 . . ?
H30 C23 H31 109.5 . . ?
C22 C23 H32 109.5 . . ?
H30 C23 H32 109.5 . . ?
H31 C23 H32 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 O1 C1 C2 -177.6(4) . . . . ?
O1 C1 C2 O2 72.4(6) . . . . ?
C1 C2 O2 C3 170.7(5) . . . . ?
C2 O2 C3 C4 -178.3(5) . . . . ?
C1 O1 C5 C14 177.5(5) . . . . ?
C1 O1 C5 C6 -2.6(7) . . . . ?
C14 C5 C6 C7 0.8(8) . . . . ?
O1 C5 C6 C7 -179.1(5) . . . . ?
C5 C6 C7 C8 -1.5(8) . . . . ?
C6 C7 C8 C13 0.0(8) . . . . ?
C6 C7 C8 C9 -179.5(5) . . . . ?
C7 C8 C9 C10 178.4(5) . . . . ?
C13 C8 C9 C10 -1.1(9) . . . . ?
C8 C9 C10 C11 -1.0(9) . . . . ?
C9 C10 C11 C12 2.1(9) . . . . ?
C10 C11 C12 C13 -1.1(9) . . . . ?
C11 C12 C13 C8 -1.0(8) . . . . ?
C11 C12 C13 C14 179.5(5) . . . . ?
C7 C8 C13 C12 -177.4(5) . . . . ?
C9 C8 C13 C12 2.1(8) . . . . ?
C7 C8 C13 C14 2.1(8) . . . . ?
C9 C8 C13 C14 -178.4(5) . . . . ?
O1 C5 C14 C13 -178.8(4) . . . . ?
C6 C5 C14 C13 1.3(8) . . . . ?
O1 C5 C14 C15 0.1(7) . . . . ?
C6 C5 C14 C15 -179.8(5) . . . . ?
C12 C13 C14 C5 176.8(5) . . . . ?
C8 C13 C14 C5 -2.7(7) . . . . ?
C12 C13 C14 C15 -2.1(8) . . . . ?
C8 C13 C14 C15 178.5(5) . . . . ?
C5 C14 C15 N1 170.7(5) . . . . ?
C13 C14 C15 N1 -10.5(8) . . . . ?
C14 C15 N1 N2 179.5(5) . . . . ?
C15 N1 N2 C16 -172.3(5) . . . . ?
N1 N2 C16 O3 177.6(5) . . . . ?
N1 N2 C16 C17 -1.3(7) . . . . ?
O3 C16 C17 C18 1.6(8) . . . . ?
N2 C16 C17 C18 -179.5(5) . . . . ?
C16 C17 C18 C19 179.6(5) . . . . ?
C17 C18 C19 C20 172.8(5) . . . . ?
C18 C19 C20 C21 178.6(5) . . . . ?
C19 C20 C21 C22 169.1(6) . . . . ?
C20 C21 C22 C23 58.7(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C15 H16 O3 0.95 2.45 3.268(7) 144.3 2_645 yes
N2 H17 O3 0.88 2.10 2.942(6) 159.6 2_645 yes

_refine_diff_density_max         0.672
_refine_diff_density_min         -0.575
_refine_diff_density_rms         0.133



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
_exptl_crystal_preparation       photochromic
####################################################################### 
# 
# 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_Z-c7
_database_code_depnum_ccdc_archive 'CCDC 2431294'
loop_
_audit_author_name
_audit_author_address
'Isao Yoshikawa'
;Institute of Industrial Science, The University of Tokyo
Japan
;
_audit_update_record             
;
2025-03-14 deposited with the CCDC.	2025-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H32 N2 O3'
_chemical_formula_sum            'C23 H32 N2 O3'
_chemical_formula_weight         384.50

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   18.5994(9)
_cell_length_b                   13.5295(6)
_cell_length_c                   8.1978(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.826(4)
_cell_angle_gamma                90
_cell_volume                     2055.59(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3843
_cell_measurement_theta_min      6.2640
_cell_measurement_theta_max      72.1950

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_shelx_estimated_absorpt_T_min   0.824
_shelx_estimated_absorpt_T_max   0.926
_exptl_absorpt_coefficient_mu    0.648
_exptl_absorpt_correction_T_min  0.655
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            10300
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         4.045
_diffrn_reflns_theta_max         73.080
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3963
_reflns_number_gt                3128
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.41.107a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0923P)²+1.7032P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3963
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0642
_refine_ls_wR_factor_ref         0.1948
_refine_ls_wR_factor_gt          0.1853
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.37014(10) 0.05197(12) 0.3594(2) 0.0370(4) Uani 1 1 d . . . . .
C1 C 0.32784(14) -0.02590(18) 0.2806(3) 0.0372(6) Uani 1 1 d . . . . .
H1 H 0.346975 -0.090944 0.318738 0.045 Uiso 1 1 calc R U . . .
H2 H 0.330203 -0.022162 0.160540 0.045 Uiso 1 1 calc R U . . .
C2 C 0.25139(15) -0.01476(19) 0.3217(3) 0.0404(6) Uani 1 1 d . . . . .
H3 H 0.249568 -0.013302 0.442067 0.048 Uiso 1 1 calc R U . . .
H4 H 0.231200 0.048145 0.276374 0.048 Uiso 1 1 calc R U . . .
O2 O 0.21005(10) -0.09548(13) 0.2545(2) 0.0421(5) Uani 1 1 d . . . . .
C3 C 0.17736(15) -0.0784(2) 0.0935(3) 0.0430(6) Uani 1 1 d . . . . .
H5 H 0.170307 -0.142472 0.036060 0.052 Uiso 1 1 calc R U . . .
H6 H 0.210147 -0.037745 0.032097 0.052 Uiso 1 1 calc R U . . .
C4 C 0.10623(17) -0.0270(2) 0.0947(4) 0.0503(7) Uani 1 1 d . . . . .
H7 H 0.074265 -0.065608 0.159404 0.075 Uiso 1 1 calc R U . . .
H8 H 0.084328 -0.020634 -0.017790 0.075 Uiso 1 1 calc R U . . .
H9 H 0.113485 0.038786 0.143167 0.075 Uiso 1 1 calc R U . . .
C5 C 0.44019(14) 0.05863(17) 0.3256(3) 0.0335(5) Uani 1 1 d . . . . .
C6 C 0.47264(14) -0.00968(18) 0.2240(3) 0.0366(6) Uani 1 1 d . . . . .
H10 H 0.444604 -0.062002 0.174403 0.044 Uiso 1 1 calc R U . . .
C7 C 0.54295(15) -0.00162(18) 0.1964(3) 0.0366(6) Uani 1 1 d . . . . .
H11 H 0.563745 -0.049554 0.129908 0.044 Uiso 1 1 calc R U . . .
C8 C 0.58638(14) 0.07639(18) 0.2639(3) 0.0352(5) Uani 1 1 d . . . . .
C9 C 0.65896(15) 0.08760(19) 0.2316(3) 0.0383(6) Uani 1 1 d . . . . .
H12 H 0.680147 0.040976 0.163419 0.046 Uiso 1 1 calc R U . . .
C10 C 0.69966(15) 0.1647(2) 0.2968(3) 0.0401(6) Uani 1 1 d . . . . .
H13 H 0.748416 0.172149 0.272525 0.048 Uiso 1 1 calc R U . . .
C11 C 0.66848(15) 0.23255(19) 0.3999(3) 0.0386(6) Uani 1 1 d . . . . .
H14 H 0.696823 0.285474 0.446434 0.046 Uiso 1 1 calc R U . . .
C12 C 0.59873(14) 0.22385(18) 0.4341(3) 0.0357(6) Uani 1 1 d . . . . .
H15 H 0.578981 0.271042 0.503573 0.043 Uiso 1 1 calc R U . . .
C13 C 0.55455(14) 0.14535(17) 0.3678(3) 0.0339(5) Uani 1 1 d . . . . .
C14 C 0.48094(14) 0.13532(17) 0.3988(3) 0.0333(5) Uani 1 1 d . . . . .
C15 C 0.45237(14) 0.20057(18) 0.5224(3) 0.0350(5) Uani 1 1 d . . . . .
H16 H 0.480095 0.200491 0.625135 0.042 Uiso 1 1 calc R U . . .
N1 N 0.39731(12) 0.25705(15) 0.5166(2) 0.0346(5) Uani 1 1 d . . . . .
N2 N 0.35447(12) 0.26372(15) 0.3719(2) 0.0340(5) Uani 1 1 d . . . . .
H17 H 0.3664(17) 0.231(2) 0.283(4) 0.051 Uiso 1 1 d . U . . .
C16 C 0.29879(14) 0.32923(17) 0.3633(3) 0.0336(5) Uani 1 1 d . . . . .
O3 O 0.28326(10) 0.37772(13) 0.4810(2) 0.0396(4) Uani 1 1 d . . . . .
C17 C 0.25860(14) 0.33813(18) 0.1964(3) 0.0363(6) Uani 1 1 d . . . . .
H18 H 0.264029 0.275904 0.135084 0.044 Uiso 1 1 calc R U . . .
H19 H 0.280104 0.392143 0.135110 0.044 Uiso 1 1 calc R U . . .
C18 C 0.17889(14) 0.35907(19) 0.2068(3) 0.0378(6) Uani 1 1 d . . . . .
H20 H 0.157867 0.384479 0.100017 0.045 Uiso 1 1 calc R U . . .
H21 H 0.173340 0.410874 0.290119 0.045 Uiso 1 1 calc R U . . .
C19 C 0.13796(15) 0.26704(19) 0.2517(3) 0.0395(6) Uani 1 1 d . . . . .
H22 H 0.138076 0.219302 0.160157 0.047 Uiso 1 1 calc R U . . .
H23 H 0.164126 0.236129 0.348749 0.047 Uiso 1 1 calc R U . . .
C20 C 0.06050(15) 0.28496(19) 0.2886(3) 0.0400(6) Uani 1 1 d . . . . .
H24 H 0.035284 0.321521 0.196052 0.048 Uiso 1 1 calc R U . . .
H25 H 0.060316 0.327089 0.387272 0.048 Uiso 1 1 calc R U . . .
C21 C 0.01913(15) 0.1904(2) 0.3168(3) 0.0415(6) Uani 1 1 d . . . . .
H26 H 0.014521 0.152150 0.213426 0.050 Uiso 1 1 calc R U . . .
H27 H 0.047748 0.150051 0.399486 0.050 Uiso 1 1 calc R U . . .
C22 C -0.05535(15) 0.2055(2) 0.3734(3) 0.0449(6) Uani 1 1 d . . . . .
H28 H -0.085664 0.240404 0.286622 0.054 Uiso 1 1 calc R U . . .
H29 H -0.051557 0.248079 0.471914 0.054 Uiso 1 1 calc R U . . .
C23 C -0.09217(18) 0.1091(2) 0.4135(4) 0.0530(7) Uani 1 1 d . . . . .
H30 H -0.100817 0.069510 0.313742 0.079 Uiso 1 1 calc R U . . .
H31 H -0.138284 0.123622 0.458111 0.079 Uiso 1 1 calc R U . . .
H32 H -0.061124 0.072195 0.494628 0.079 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.358(3) . ?
O1 C1 1.435(3) . ?
C1 C2 1.497(4) . ?
C1 H1 0.9900 . ?
C1 H2 0.9900 . ?
C2 O2 1.420(3) . ?
C2 H3 0.9900 . ?
C2 H4 0.9900 . ?
O2 C3 1.424(3) . ?
C3 C4 1.495(4) . ?
C3 H5 0.9900 . ?
C3 H6 0.9900 . ?
C4 H7 0.9800 . ?
C4 H8 0.9800 . ?
C4 H9 0.9800 . ?
C5 C14 1.391(3) . ?
C5 C6 1.413(3) . ?
C6 C7 1.350(4) . ?
C6 H10 0.9500 . ?
C7 C8 1.413(4) . ?
C7 H11 0.9500 . ?
C8 C9 1.406(4) . ?
C8 C13 1.425(3) . ?
C9 C10 1.370(4) . ?
C9 H12 0.9500 . ?
C10 C11 1.406(4) . ?
C10 H13 0.9500 . ?
C11 C12 1.355(4) . ?
C11 H14 0.9500 . ?
C12 C13 1.422(3) . ?
C12 H15 0.9500 . ?
C13 C14 1.420(4) . ?
C14 C15 1.476(3) . ?
C15 N1 1.275(3) . ?
C15 H16 0.9500 . ?
N1 N2 1.375(3) . ?
N2 C16 1.360(3) . ?
N2 H17 0.89(3) . ?
C16 O3 1.222(3) . ?
C16 C17 1.508(3) . ?
C17 C18 1.519(4) . ?
C17 H18 0.9900 . ?
C17 H19 0.9900 . ?
C18 C19 1.520(4) . ?
C18 H20 0.9900 . ?
C18 H21 0.9900 . ?
C19 C20 1.516(4) . ?
C19 H22 0.9900 . ?
C19 H23 0.9900 . ?
C20 C21 1.521(4) . ?
C20 H24 0.9900 . ?
C20 H25 0.9900 . ?
C21 C22 1.511(4) . ?
C21 H26 0.9900 . ?
C21 H27 0.9900 . ?
C22 C23 1.521(4) . ?
C22 H28 0.9900 . ?
C22 H29 0.9900 . ?
C23 H30 0.9800 . ?
C23 H31 0.9800 . ?
C23 H32 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C1 117.12(18) . . ?
O1 C1 C2 108.6(2) . . ?
O1 C1 H1 110.0 . . ?
C2 C1 H1 110.0 . . ?
O1 C1 H2 110.0 . . ?
C2 C1 H2 110.0 . . ?
H1 C1 H2 108.3 . . ?
O2 C2 C1 109.2(2) . . ?
O2 C2 H3 109.8 . . ?
C1 C2 H3 109.8 . . ?
O2 C2 H4 109.8 . . ?
C1 C2 H4 109.8 . . ?
H3 C2 H4 108.3 . . ?
C2 O2 C3 114.2(2) . . ?
O2 C3 C4 112.2(2) . . ?
O2 C3 H5 109.2 . . ?
C4 C3 H5 109.2 . . ?
O2 C3 H6 109.2 . . ?
C4 C3 H6 109.2 . . ?
H5 C3 H6 107.9 . . ?
C3 C4 H7 109.5 . . ?
C3 C4 H8 109.5 . . ?
H7 C4 H8 109.5 . . ?
C3 C4 H9 109.5 . . ?
H7 C4 H9 109.5 . . ?
H8 C4 H9 109.5 . . ?
O1 C5 C14 117.3(2) . . ?
O1 C5 C6 122.8(2) . . ?
C14 C5 C6 119.9(2) . . ?
C7 C6 C5 120.9(2) . . ?
C7 C6 H10 119.5 . . ?
C5 C6 H10 119.5 . . ?
C6 C7 C8 121.6(2) . . ?
C6 C7 H11 119.2 . . ?
C8 C7 H11 119.2 . . ?
C9 C8 C7 122.2(2) . . ?
C9 C8 C13 119.7(2) . . ?
C7 C8 C13 118.1(2) . . ?
C10 C9 C8 121.1(2) . . ?
C10 C9 H12 119.5 . . ?
C8 C9 H12 119.5 . . ?
C9 C10 C11 119.3(3) . . ?
C9 C10 H13 120.4 . . ?
C11 C10 H13 120.4 . . ?
C12 C11 C10 121.2(2) . . ?
C12 C11 H14 119.4 . . ?
C10 C11 H14 119.4 . . ?
C11 C12 C13 121.2(2) . . ?
C11 C12 H15 119.4 . . ?
C13 C12 H15 119.4 . . ?
C14 C13 C12 122.5(2) . . ?
C14 C13 C8 120.0(2) . . ?
C12 C13 C8 117.5(2) . . ?
C5 C14 C13 119.5(2) . . ?
C5 C14 C15 121.9(2) . . ?
C13 C14 C15 118.3(2) . . ?
N1 C15 C14 131.9(2) . . ?
N1 C15 H16 114.1 . . ?
C14 C15 H16 114.1 . . ?
C15 N1 N2 118.5(2) . . ?
C16 N2 N1 118.1(2) . . ?
C16 N2 H17 121(2) . . ?
N1 N2 H17 120(2) . . ?
O3 C16 N2 122.6(2) . . ?
O3 C16 C17 122.8(2) . . ?
N2 C16 C17 114.6(2) . . ?
C16 C17 C18 112.1(2) . . ?
C16 C17 H18 109.2 . . ?
C18 C17 H18 109.2 . . ?
C16 C17 H19 109.2 . . ?
C18 C17 H19 109.2 . . ?
H18 C17 H19 107.9 . . ?
C17 C18 C19 111.8(2) . . ?
C17 C18 H20 109.3 . . ?
C19 C18 H20 109.3 . . ?
C17 C18 H21 109.3 . . ?
C19 C18 H21 109.3 . . ?
H20 C18 H21 107.9 . . ?
C20 C19 C18 114.9(2) . . ?
C20 C19 H22 108.5 . . ?
C18 C19 H22 108.5 . . ?
C20 C19 H23 108.5 . . ?
C18 C19 H23 108.5 . . ?
H22 C19 H23 107.5 . . ?
C19 C20 C21 113.4(2) . . ?
C19 C20 H24 108.9 . . ?
C21 C20 H24 108.9 . . ?
C19 C20 H25 108.9 . . ?
C21 C20 H25 108.9 . . ?
H24 C20 H25 107.7 . . ?
C22 C21 C20 114.9(2) . . ?
C22 C21 H26 108.5 . . ?
C20 C21 H26 108.5 . . ?
C22 C21 H27 108.5 . . ?
C20 C21 H27 108.5 . . ?
H26 C21 H27 107.5 . . ?
C21 C22 C23 113.1(2) . . ?
C21 C22 H28 109.0 . . ?
C23 C22 H28 109.0 . . ?
C21 C22 H29 109.0 . . ?
C23 C22 H29 109.0 . . ?
H28 C22 H29 107.8 . . ?
C22 C23 H30 109.5 . . ?
C22 C23 H31 109.5 . . ?
H30 C23 H31 109.5 . . ?
C22 C23 H32 109.5 . . ?
H30 C23 H32 109.5 . . ?
H31 C23 H32 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 O1 C1 C2 -174.92(19) . . . . ?
O1 C1 C2 O2 -175.74(18) . . . . ?
C1 C2 O2 C3 -90.8(3) . . . . ?
C2 O2 C3 C4 -85.6(3) . . . . ?
C1 O1 C5 C14 178.6(2) . . . . ?
C1 O1 C5 C6 -2.9(3) . . . . ?
O1 C5 C6 C7 -178.5(2) . . . . ?
C14 C5 C6 C7 -0.1(4) . . . . ?
C5 C6 C7 C8 -1.7(4) . . . . ?
C6 C7 C8 C9 -177.8(2) . . . . ?
C6 C7 C8 C13 2.1(3) . . . . ?
C7 C8 C9 C10 179.1(2) . . . . ?
C13 C8 C9 C10 -0.8(4) . . . . ?
C8 C9 C10 C11 1.1(4) . . . . ?
C9 C10 C11 C12 -0.9(4) . . . . ?
C10 C11 C12 C13 0.4(4) . . . . ?
C11 C12 C13 C14 -178.8(2) . . . . ?
C11 C12 C13 C8 -0.1(3) . . . . ?
C9 C8 C13 C14 179.0(2) . . . . ?
C7 C8 C13 C14 -0.9(3) . . . . ?
C9 C8 C13 C12 0.3(3) . . . . ?
C7 C8 C13 C12 -179.6(2) . . . . ?
O1 C5 C14 C13 179.82(19) . . . . ?
C6 C5 C14 C13 1.3(3) . . . . ?
O1 C5 C14 C15 6.6(3) . . . . ?
C6 C5 C14 C15 -171.9(2) . . . . ?
C12 C13 C14 C5 177.8(2) . . . . ?
C8 C13 C14 C5 -0.8(3) . . . . ?
C12 C13 C14 C15 -8.7(3) . . . . ?
C8 C13 C14 C15 172.7(2) . . . . ?
C5 C14 C15 N1 -58.8(4) . . . . ?
C13 C14 C15 N1 127.9(3) . . . . ?
C14 C15 N1 N2 -1.2(4) . . . . ?
C15 N1 N2 C16 -175.5(2) . . . . ?
N1 N2 C16 O3 -4.2(3) . . . . ?
N1 N2 C16 C17 175.0(2) . . . . ?
O3 C16 C17 C18 -34.1(3) . . . . ?
N2 C16 C17 C18 146.7(2) . . . . ?
C16 C17 C18 C19 -76.3(3) . . . . ?
C17 C18 C19 C20 171.5(2) . . . . ?
C18 C19 C20 C21 174.4(2) . . . . ?
C19 C20 C21 C22 173.1(2) . . . . ?
C20 C21 C22 C23 -175.2(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H2 O3 0.99 2.56 3.224(3) 124.7 4_565 yes
N2 H17 N1 0.89(3) 2.31(3) 3.096(3) 146(3) 4_565 yes
C17 H18 O3 0.99 2.47 3.463(3) 177.5 4_565 yes

_refine_diff_density_max         0.324
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.069



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_E-e7-A
_database_code_depnum_ccdc_archive 'CCDC 2431300'
loop_
_audit_author_name
_audit_author_address
'Isao Yoshikawa'
;Institute of Industrial Science, The University of Tokyo
Japan
;
_audit_update_record             
;
2025-03-14 deposited with the CCDC.	2025-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H30 N2 O4'
_chemical_formula_sum            'C23 H30 N2 O4'
_chemical_formula_weight         398.49

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   11.0325(4)
_cell_length_b                   4.8266(2)
_cell_length_c                   39.7434(11)
_cell_angle_alpha                90
_cell_angle_beta                 92.711(3)
_cell_angle_gamma                90
_cell_volume                     2113.95(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    7483
_cell_measurement_theta_min      4.1210
_cell_measurement_theta_max      72.5310

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.691
_shelx_estimated_absorpt_T_min   0.794
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_T_min  0.679
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            18530
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_theta_min         2.226
_diffrn_reflns_theta_max         72.648
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4131
_reflns_number_gt                3408
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.41.107a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0826P)²+1.5266P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4131
_refine_ls_number_parameters     267
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1645
_refine_ls_wR_factor_gt          0.1580
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.19526(13) 1.2185(3) 0.05589(4) 0.0270(3) Uani 1 1 d . . . . .
C1 C 0.15769(19) 1.3788(4) 0.02742(5) 0.0264(4) Uani 1 1 d . . . . .
H1 H 0.081239 1.476308 0.031979 0.032 Uiso 1 1 calc R U . . .
H2 H 0.141770 1.255136 0.007831 0.032 Uiso 1 1 calc R U . . .
C2 C 0.2530(2) 1.5871(4) 0.01921(5) 0.0276(5) Uani 1 1 d . . . . .
O2 O 0.23324(15) 1.7603(3) -0.00242(4) 0.0339(4) Uani 1 1 d . . . . .
O3 O 0.35695(14) 1.5589(3) 0.03706(4) 0.0314(4) Uani 1 1 d . . . . .
C3 C 0.4476(2) 1.7692(5) 0.03118(6) 0.0360(5) Uani 1 1 d . . . . .
H3 H 0.416890 1.954166 0.037385 0.043 Uiso 1 1 calc R U . . .
H4 H 0.466337 1.772487 0.007070 0.043 Uiso 1 1 calc R U . . .
C4 C 0.5592(2) 1.6997(6) 0.05236(6) 0.0430(6) Uani 1 1 d . . . . .
H5 H 0.538399 1.683372 0.075984 0.064 Uiso 1 1 calc R U . . .
H6 H 0.619614 1.846678 0.050200 0.064 Uiso 1 1 calc R U . . .
H7 H 0.592641 1.523562 0.044782 0.064 Uiso 1 1 calc R U . . .
C5 C 0.11278(18) 1.0346(4) 0.06791(5) 0.0239(4) Uani 1 1 d . . . . .
C6 C -0.00341(19) 0.9951(4) 0.05269(5) 0.0268(5) Uani 1 1 d . . . . .
H8 H -0.029425 1.101928 0.033610 0.032 Uiso 1 1 calc R U . . .
C7 C -0.07889(19) 0.8008(5) 0.06564(5) 0.0272(5) Uani 1 1 d . . . . .
H9 H -0.157027 0.772640 0.055117 0.033 Uiso 1 1 calc R U . . .
C8 C -0.04338(19) 0.6408(4) 0.09432(5) 0.0261(4) Uani 1 1 d . . . . .
C9 C -0.1222(2) 0.4429(5) 0.10761(5) 0.0296(5) Uani 1 1 d . . . . .
H10 H -0.199900 0.413445 0.096859 0.036 Uiso 1 1 calc R U . . .
C10 C -0.0888(2) 0.2932(5) 0.13567(6) 0.0304(5) Uani 1 1 d . . . . .
H11 H -0.142055 0.158106 0.144114 0.037 Uiso 1 1 calc R U . . .
C11 C 0.0251(2) 0.3405(5) 0.15195(5) 0.0298(5) Uani 1 1 d . . . . .
H12 H 0.047574 0.239436 0.171792 0.036 Uiso 1 1 calc R U . . .
C12 C 0.10425(19) 0.5297(4) 0.13973(5) 0.0264(4) Uani 1 1 d . . . . .
H13 H 0.180652 0.558184 0.151250 0.032 Uiso 1 1 calc R U . . .
C13 C 0.07390(19) 0.6844(4) 0.11003(5) 0.0245(4) Uani 1 1 d . . . . .
C14 C 0.15302(18) 0.8846(4) 0.09612(5) 0.0240(4) Uani 1 1 d . . . . .
C15 C 0.27440(19) 0.9501(4) 0.11068(5) 0.0249(4) Uani 1 1 d . . . . .
H14 H 0.302080 1.136430 0.110547 0.030 Uiso 1 1 calc R U . . .
N1 N 0.34367(15) 0.7618(4) 0.12354(4) 0.0255(4) Uani 1 1 d . . . . .
N2 N 0.45364(16) 0.8553(4) 0.13686(4) 0.0250(4) Uani 1 1 d . . . . .
H15 H 0.471(2) 1.032(6) 0.1383(7) 0.037 Uiso 1 1 d . U . . .
C16 C 0.53911(19) 0.6722(4) 0.14770(5) 0.0257(4) Uani 1 1 d . . . . .
O4 O 0.52465(15) 0.4197(3) 0.14659(4) 0.0359(4) Uani 1 1 d . . . . .
C17 C 0.65749(18) 0.7993(4) 0.16035(5) 0.0261(4) Uani 1 1 d . . . . .
H16 H 0.644006 0.997567 0.165372 0.031 Uiso 1 1 calc R U . . .
H17 H 0.716256 0.788885 0.142327 0.031 Uiso 1 1 calc R U . . .
C18 C 0.71198(18) 0.6583(4) 0.19178(5) 0.0262(4) Uani 1 1 d . . . . .
H18 H 0.721474 0.457976 0.187227 0.031 Uiso 1 1 calc R U . . .
H19 H 0.655600 0.678355 0.210279 0.031 Uiso 1 1 calc R U . . .
C19 C 0.83506(19) 0.7798(4) 0.20294(5) 0.0263(4) Uani 1 1 d . . . . .
H20 H 0.890636 0.762549 0.184210 0.032 Uiso 1 1 calc R U . . .
H21 H 0.824967 0.979682 0.207670 0.032 Uiso 1 1 calc R U . . .
C20 C 0.8928(2) 0.6404(5) 0.23404(5) 0.0294(5) Uani 1 1 d . . . . .
H22 H 0.900131 0.439498 0.229563 0.035 Uiso 1 1 calc R U . . .
H23 H 0.838402 0.663319 0.252952 0.035 Uiso 1 1 calc R U . . .
C21 C 1.01746(19) 0.7536(5) 0.24468(5) 0.0297(5) Uani 1 1 d . . . . .
H24 H 1.073524 0.720816 0.226367 0.036 Uiso 1 1 calc R U . . .
H25 H 1.011371 0.956311 0.248036 0.036 Uiso 1 1 calc R U . . .
C22 C 1.0699(2) 0.6218(5) 0.27688(6) 0.0354(5) Uani 1 1 d . . . . .
H26 H 1.012326 0.649865 0.294943 0.042 Uiso 1 1 calc R U . . .
H27 H 1.077631 0.419753 0.273244 0.042 Uiso 1 1 calc R U . . .
C23 C 1.1929(2) 0.7367(6) 0.28859(7) 0.0431(6) Uani 1 1 d . . . . .
H28 H 1.250543 0.710237 0.270851 0.065 Uiso 1 1 calc R U . . .
H29 H 1.222158 0.639083 0.309011 0.065 Uiso 1 1 calc R U . . .
H30 H 1.185274 0.934777 0.293451 0.065 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.373(2) . ?
O1 C1 1.417(2) . ?
C1 C2 1.502(3) . ?
C1 H1 0.9900 . ?
C1 H2 0.9900 . ?
C2 O2 1.211(3) . ?
C2 O3 1.327(3) . ?
O3 C3 1.452(3) . ?
C3 C4 1.496(3) . ?
C3 H3 0.9900 . ?
C3 H4 0.9900 . ?
C4 H5 0.9800 . ?
C4 H6 0.9800 . ?
C4 H7 0.9800 . ?
C5 C14 1.390(3) . ?
C5 C6 1.404(3) . ?
C6 C7 1.371(3) . ?
C6 H8 0.9500 . ?
C7 C8 1.417(3) . ?
C7 H9 0.9500 . ?
C8 C9 1.411(3) . ?
C8 C13 1.425(3) . ?
C9 C10 1.365(3) . ?
C9 H10 0.9500 . ?
C10 C11 1.404(3) . ?
C10 H11 0.9500 . ?
C11 C12 1.368(3) . ?
C11 H12 0.9500 . ?
C12 C13 1.424(3) . ?
C12 H13 0.9500 . ?
C13 C14 1.430(3) . ?
C14 C15 1.468(3) . ?
C15 N1 1.278(3) . ?
C15 H14 0.9500 . ?
N1 N2 1.377(2) . ?
N2 C16 1.348(3) . ?
N2 H15 0.88(3) . ?
C16 O4 1.230(3) . ?
C16 C17 1.508(3) . ?
C17 C18 1.521(3) . ?
C17 H16 0.9900 . ?
C17 H17 0.9900 . ?
C18 C19 1.526(3) . ?
C18 H18 0.9900 . ?
C18 H19 0.9900 . ?
C19 C20 1.521(3) . ?
C19 H20 0.9900 . ?
C19 H21 0.9900 . ?
C20 C21 1.521(3) . ?
C20 H22 0.9900 . ?
C20 H23 0.9900 . ?
C21 C22 1.519(3) . ?
C21 H24 0.9900 . ?
C21 H25 0.9900 . ?
C22 C23 1.518(3) . ?
C22 H26 0.9900 . ?
C22 H27 0.9900 . ?
C23 H28 0.9800 . ?
C23 H29 0.9800 . ?
C23 H30 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C1 117.21(16) . . ?
O1 C1 C2 110.97(17) . . ?
O1 C1 H1 109.4 . . ?
C2 C1 H1 109.4 . . ?
O1 C1 H2 109.4 . . ?
C2 C1 H2 109.4 . . ?
H1 C1 H2 108.0 . . ?
O2 C2 O3 124.9(2) . . ?
O2 C2 C1 120.8(2) . . ?
O3 C2 C1 114.30(18) . . ?
C2 O3 C3 115.25(17) . . ?
O3 C3 C4 107.9(2) . . ?
O3 C3 H3 110.1 . . ?
C4 C3 H3 110.1 . . ?
O3 C3 H4 110.1 . . ?
C4 C3 H4 110.1 . . ?
H3 C3 H4 108.4 . . ?
C3 C4 H5 109.5 . . ?
C3 C4 H6 109.5 . . ?
H5 C4 H6 109.5 . . ?
C3 C4 H7 109.5 . . ?
H5 C4 H7 109.5 . . ?
H6 C4 H7 109.5 . . ?
O1 C5 C14 115.20(18) . . ?
O1 C5 C6 122.99(18) . . ?
C14 C5 C6 121.80(19) . . ?
C7 C6 C5 119.30(19) . . ?
C7 C6 H8 120.3 . . ?
C5 C6 H8 120.3 . . ?
C6 C7 C8 121.70(19) . . ?
C6 C7 H9 119.1 . . ?
C8 C7 H9 119.1 . . ?
C9 C8 C7 121.21(19) . . ?
C9 C8 C13 119.93(19) . . ?
C7 C8 C13 118.85(19) . . ?
C10 C9 C8 121.1(2) . . ?
C10 C9 H10 119.5 . . ?
C8 C9 H10 119.5 . . ?
C9 C10 C11 119.5(2) . . ?
C9 C10 H11 120.3 . . ?
C11 C10 H11 120.3 . . ?
C12 C11 C10 121.1(2) . . ?
C12 C11 H12 119.4 . . ?
C10 C11 H12 119.4 . . ?
C11 C12 C13 121.0(2) . . ?
C11 C12 H13 119.5 . . ?
C13 C12 H13 119.5 . . ?
C12 C13 C8 117.30(19) . . ?
C12 C13 C14 123.42(19) . . ?
C8 C13 C14 119.24(18) . . ?
C5 C14 C13 119.08(18) . . ?
C5 C14 C15 117.16(18) . . ?
C13 C14 C15 123.72(18) . . ?
N1 C15 C14 121.43(19) . . ?
N1 C15 H14 119.3 . . ?
C14 C15 H14 119.3 . . ?
C15 N1 N2 114.84(18) . . ?
C16 N2 N1 119.90(18) . . ?
C16 N2 H15 118.0(18) . . ?
N1 N2 H15 122.1(18) . . ?
O4 C16 N2 123.40(19) . . ?
O4 C16 C17 121.62(19) . . ?
N2 C16 C17 114.94(18) . . ?
C16 C17 C18 113.21(18) . . ?
C16 C17 H16 108.9 . . ?
C18 C17 H16 108.9 . . ?
C16 C17 H17 108.9 . . ?
C18 C17 H17 108.9 . . ?
H16 C17 H17 107.7 . . ?
C17 C18 C19 112.23(18) . . ?
C17 C18 H18 109.2 . . ?
C19 C18 H18 109.2 . . ?
C17 C18 H19 109.2 . . ?
C19 C18 H19 109.2 . . ?
H18 C18 H19 107.9 . . ?
C20 C19 C18 113.52(18) . . ?
C20 C19 H20 108.9 . . ?
C18 C19 H20 108.9 . . ?
C20 C19 H21 108.9 . . ?
C18 C19 H21 108.9 . . ?
H20 C19 H21 107.7 . . ?
C19 C20 C21 113.93(18) . . ?
C19 C20 H22 108.8 . . ?
C21 C20 H22 108.8 . . ?
C19 C20 H23 108.8 . . ?
C21 C20 H23 108.8 . . ?
H22 C20 H23 107.7 . . ?
C22 C21 C20 112.76(19) . . ?
C22 C21 H24 109.0 . . ?
C20 C21 H24 109.0 . . ?
C22 C21 H25 109.0 . . ?
C20 C21 H25 109.0 . . ?
H24 C21 H25 107.8 . . ?
C23 C22 C21 113.8(2) . . ?
C23 C22 H26 108.8 . . ?
C21 C22 H26 108.8 . . ?
C23 C22 H27 108.8 . . ?
C21 C22 H27 108.8 . . ?
H26 C22 H27 107.7 . . ?
C22 C23 H28 109.5 . . ?
C22 C23 H29 109.5 . . ?
H28 C23 H29 109.5 . . ?
C22 C23 H30 109.5 . . ?
H28 C23 H30 109.5 . . ?
H29 C23 H30 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 O1 C1 C2 174.87(17) . . . . ?
O1 C1 C2 O2 -173.25(19) . . . . ?
O1 C1 C2 O3 7.7(3) . . . . ?
O2 C2 O3 C3 5.0(3) . . . . ?
C1 C2 O3 C3 -176.03(18) . . . . ?
C2 O3 C3 C4 -178.13(19) . . . . ?
C1 O1 C5 C14 -179.17(18) . . . . ?
C1 O1 C5 C6 1.9(3) . . . . ?
O1 C5 C6 C7 177.89(19) . . . . ?
C14 C5 C6 C7 -0.9(3) . . . . ?
C5 C6 C7 C8 0.9(3) . . . . ?
C6 C7 C8 C9 179.5(2) . . . . ?
C6 C7 C8 C13 0.1(3) . . . . ?
C7 C8 C9 C10 -178.6(2) . . . . ?
C13 C8 C9 C10 0.7(3) . . . . ?
C8 C9 C10 C11 1.2(3) . . . . ?
C9 C10 C11 C12 -1.5(3) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C11 C12 C13 C8 2.1(3) . . . . ?
C11 C12 C13 C14 -180.0(2) . . . . ?
C9 C8 C13 C12 -2.3(3) . . . . ?
C7 C8 C13 C12 177.02(19) . . . . ?
C9 C8 C13 C14 179.63(19) . . . . ?
C7 C8 C13 C14 -1.0(3) . . . . ?
O1 C5 C14 C13 -178.88(17) . . . . ?
C6 C5 C14 C13 0.0(3) . . . . ?
O1 C5 C14 C15 3.3(3) . . . . ?
C6 C5 C14 C15 -177.82(19) . . . . ?
C12 C13 C14 C5 -176.96(19) . . . . ?
C8 C13 C14 C5 0.9(3) . . . . ?
C12 C13 C14 C15 0.7(3) . . . . ?
C8 C13 C14 C15 178.63(19) . . . . ?
C5 C14 C15 N1 -144.4(2) . . . . ?
C13 C14 C15 N1 37.9(3) . . . . ?
C14 C15 N1 N2 -178.64(17) . . . . ?
C15 N1 N2 C16 -172.69(19) . . . . ?
N1 N2 C16 O4 -0.4(3) . . . . ?
N1 N2 C16 C17 177.47(17) . . . . ?
O4 C16 C17 C18 -42.7(3) . . . . ?
N2 C16 C17 C18 139.42(19) . . . . ?
C16 C17 C18 C19 176.77(17) . . . . ?
C17 C18 C19 C20 -179.19(18) . . . . ?
C18 C19 C20 C21 178.05(18) . . . . ?
C19 C20 C21 C22 176.83(19) . . . . ?
C20 C21 C22 C23 -178.4(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C6 H8 O2 0.95 2.60 3.367(3) 137.8 3_585 yes
N2 H15 O4 0.88(3) 1.99(3) 2.856(2) 173(3) 1_565 yes
C17 H16 O4 0.99 2.52 3.367(3) 143.4 1_565 yes

_refine_diff_density_max         0.287
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.062



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
_exptl_crystal_preparation       photochromic
####################################################################### 
# 
# 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_E-b7
_database_code_depnum_ccdc_archive 'CCDC 2431296'
loop_
_audit_author_name
_audit_author_address
'Isao Yoshikawa'
;Institute of Industrial Science, The University of Tokyo
Japan
;
_audit_update_record             
;
2025-03-14 deposited with the CCDC.	2025-07-08 downloaded from the CCDC.
;

_vrf_PLAT084_E-b7                
;
PROBLEM: High wR2 Value (i.e. > 0.25) ................... 0.55 Report
RESPONSE: Quality of the crystals were low.
;
_vrf_PLAT934_E-b7                
;
PROBLEM: Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers .. 24 Check
RESPONSE: Quality of the crystals were low.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H34 N2 O2'
_chemical_formula_sum            'C24 H34 N2 O2'
_chemical_formula_weight         382.53

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.0009(9)
_cell_length_b                   6.1674(7)
_cell_length_c                   33.376(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.601(9)
_cell_angle_gamma                90
_cell_volume                     2239.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3926
_cell_measurement_theta_min      2.8310
_cell_measurement_theta_max      72.0650

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.135
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.080
_shelx_estimated_absorpt_T_min   0.775
_shelx_estimated_absorpt_T_max   0.957
_exptl_absorpt_coefficient_mu    0.561
_exptl_absorpt_correction_T_min  0.546
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            10265
_diffrn_reflns_av_unetI/netI     0.0809
_diffrn_reflns_av_R_equivalents  0.1019
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         2.678
_diffrn_reflns_theta_max         72.647
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             4258
_reflns_number_gt                3175
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.41.107a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4258
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2180
_refine_ls_R_factor_gt           0.1867
_refine_ls_wR_factor_ref         0.5497
_refine_ls_wR_factor_gt          0.5089
_refine_ls_goodness_of_fit_ref   2.422
_refine_ls_restrained_S_all      2.422
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2608(3) 0.9337(7) 0.27574(10) 0.0338(10) Uani 1 1 d . . . . .
C1 C 0.2616(5) 1.1108(11) 0.30424(15) 0.0379(14) Uani 1 1 d . . . . .
H1 H 0.180598 1.123396 0.313546 0.045 Uiso 1 1 calc R U . . .
H2 H 0.279911 1.249277 0.291384 0.045 Uiso 1 1 calc R U . . .
C2 C 0.3605(5) 1.0598(11) 0.33956(15) 0.0375(14) Uani 1 1 d . . . . .
H3 H 0.370650 1.186506 0.357978 0.045 Uiso 1 1 calc R U . . .
H4 H 0.439303 1.037620 0.329184 0.045 Uiso 1 1 calc R U . . .
C3 C 0.3340(5) 0.8615(12) 0.36359(16) 0.0418(15) Uani 1 1 d . . . . .
H5 H 0.338350 0.731535 0.346460 0.050 Uiso 1 1 calc R U . . .
H6 H 0.248931 0.872178 0.369723 0.050 Uiso 1 1 calc R U . . .
C4 C 0.4203(5) 0.8298(11) 0.40297(15) 0.0412(15) Uani 1 1 d . . . . .
H7 H 0.420259 0.963207 0.419467 0.049 Uiso 1 1 calc R U . . .
H8 H 0.504823 0.808732 0.396805 0.049 Uiso 1 1 calc R U . . .
C5 C 0.3868(6) 0.6374(13) 0.42790(17) 0.0504(18) Uani 1 1 d . . . . .
H9 H 0.304402 0.659271 0.435031 0.076 Uiso 1 1 calc R U . . .
H10 H 0.446541 0.625295 0.452706 0.076 Uiso 1 1 calc R U . . .
H11 H 0.387817 0.504084 0.411982 0.076 Uiso 1 1 calc R U . . .
C6 C 0.1726(5) 0.9330(10) 0.24166(14) 0.0323(13) Uani 1 1 d . . . . .
C7 C 0.0853(5) 1.1026(11) 0.23412(15) 0.0373(14) Uani 1 1 d . . . . .
H12 H 0.084469 1.217134 0.253100 0.045 Uiso 1 1 calc R U . . .
C8 C 0.0020(5) 1.0999(11) 0.19924(16) 0.0361(14) Uani 1 1 d . . . . .
H13 H -0.055648 1.214774 0.193761 0.043 Uiso 1 1 calc R U . . .
C9 C 0.0013(5) 0.9261(10) 0.17115(15) 0.0341(13) Uani 1 1 d . . . . .
C10 C -0.0868(5) 0.9273(12) 0.13475(16) 0.0413(15) Uani 1 1 d . . . . .
H14 H -0.142250 1.045431 0.129351 0.050 Uiso 1 1 calc R U . . .
C11 C -0.0913(5) 0.7597(11) 0.10791(15) 0.0392(14) Uani 1 1 d . . . . .
H15 H -0.149005 0.762353 0.083694 0.047 Uiso 1 1 calc R U . . .
C12 C -0.0105(5) 0.5827(11) 0.11610(16) 0.0390(14) Uani 1 1 d . . . . .
H16 H -0.015741 0.464559 0.097666 0.047 Uiso 1 1 calc R U . . .
C13 C 0.0762(5) 0.5787(11) 0.15053(15) 0.0356(14) Uani 1 1 d . . . . .
H17 H 0.130483 0.458631 0.155414 0.043 Uiso 1 1 calc R U . . .
C14 C 0.0852(4) 0.7531(10) 0.17882(13) 0.0307(12) Uani 1 1 d . . . . .
C15 C 0.1770(4) 0.7595(10) 0.21520(14) 0.0327(13) Uani 1 1 d . . . . .
C16 C 0.2715(5) 0.5996(10) 0.22642(14) 0.0299(12) Uani 1 1 d . . . . .
H18 H 0.319063 0.609108 0.252562 0.036 Uiso 1 1 calc R U . . .
N1 N 0.2948(4) 0.4445(8) 0.20290(12) 0.0319(11) Uani 1 1 d . . . . .
N2 N 0.3881(4) 0.3026(8) 0.21748(13) 0.0316(11) Uani 1 1 d . . . . .
H19 H 0.423(5) 0.322(10) 0.2422(15) 0.022(13) Uiso 1 1 d . . . . .
C17 C 0.4062(5) 0.1311(11) 0.19482(15) 0.0356(14) Uani 1 1 d . . . . .
O2 O 0.4867(3) -0.0058(7) 0.20721(10) 0.0380(11) Uani 1 1 d . . . . .
C18 C 0.3227(5) 0.1059(10) 0.15456(14) 0.0329(13) Uani 1 1 d . . . . .
H20 H 0.236419 0.101102 0.159728 0.040 Uiso 1 1 calc R U . . .
H21 H 0.331627 0.235994 0.137864 0.040 Uiso 1 1 calc R U . . .
C19 C 0.3468(5) -0.0929(10) 0.13046(14) 0.0342(13) Uani 1 1 d . . . . .
H22 H 0.334262 -0.224428 0.146338 0.041 Uiso 1 1 calc R U . . .
H23 H 0.433437 -0.091630 0.125632 0.041 Uiso 1 1 calc R U . . .
C20 C 0.2622(5) -0.1018(11) 0.08986(15) 0.0397(15) Uani 1 1 d . . . . .
H24 H 0.282088 0.020581 0.072789 0.048 Uiso 1 1 calc R U . . .
H25 H 0.176046 -0.083633 0.094611 0.048 Uiso 1 1 calc R U . . .
C21 C 0.2731(5) -0.3143(11) 0.06698(16) 0.0406(15) Uani 1 1 d . . . . .
H26 H 0.359247 -0.333002 0.062347 0.049 Uiso 1 1 calc R U . . .
H27 H 0.252608 -0.436745 0.083963 0.049 Uiso 1 1 calc R U . . .
C22 C 0.1892(6) -0.3220(13) 0.02651(17) 0.0509(18) Uani 1 1 d . . . . .
H28 H 0.220475 -0.219899 0.007551 0.061 Uiso 1 1 calc R U . . .
H29 H 0.105996 -0.273319 0.030338 0.061 Uiso 1 1 calc R U . . .
C23 C 0.1801(7) -0.5513(15) 0.0074(2) 0.061(2) Uani 1 1 d . . . . .
H30 H 0.144896 -0.651571 0.025825 0.074 Uiso 1 1 calc R U . . .
H31 H 0.122986 -0.546188 -0.018441 0.074 Uiso 1 1 calc R U . . .
C24 C 0.3028(8) -0.6402(16) -0.00053(19) 0.064(2) Uani 1 1 d . . . . .
H32 H 0.341171 -0.536848 -0.017102 0.096 Uiso 1 1 calc R U . . .
H33 H 0.289846 -0.778699 -0.014936 0.096 Uiso 1 1 calc R U . . .
H34 H 0.356665 -0.662601 0.025298 0.096 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.380(6) . ?
O1 C1 1.448(7) . ?
C1 C2 1.513(7) . ?
C1 H1 0.9900 . ?
C1 H2 0.9900 . ?
C2 C3 1.514(9) . ?
C2 H3 0.9900 . ?
C2 H4 0.9900 . ?
C3 C4 1.515(7) . ?
C3 H5 0.9900 . ?
C3 H6 0.9900 . ?
C4 C5 1.526(9) . ?
C4 H7 0.9900 . ?
C4 H8 0.9900 . ?
C5 H9 0.9800 . ?
C5 H10 0.9800 . ?
C5 H11 0.9800 . ?
C6 C15 1.393(8) . ?
C6 C7 1.417(8) . ?
C7 C8 1.370(8) . ?
C7 H12 0.9500 . ?
C8 C9 1.423(8) . ?
C8 H13 0.9500 . ?
C9 C14 1.409(8) . ?
C9 C10 1.436(8) . ?
C10 C11 1.364(9) . ?
C10 H14 0.9500 . ?
C11 C12 1.409(9) . ?
C11 H15 0.9500 . ?
C12 C13 1.379(7) . ?
C12 H16 0.9500 . ?
C13 C14 1.425(8) . ?
C13 H17 0.9500 . ?
C14 C15 1.459(7) . ?
C15 C16 1.441(7) . ?
C16 N1 1.287(7) . ?
C16 H18 0.9500 . ?
N1 N2 1.381(6) . ?
N2 C17 1.332(8) . ?
N2 H19 0.86(5) . ?
C17 O2 1.249(7) . ?
C17 C18 1.518(7) . ?
C18 C19 1.512(8) . ?
C18 H20 0.9900 . ?
C18 H21 0.9900 . ?
C19 C20 1.526(7) . ?
C19 H22 0.9900 . ?
C19 H23 0.9900 . ?
C20 C21 1.531(9) . ?
C20 H24 0.9900 . ?
C20 H25 0.9900 . ?
C21 C22 1.518(8) . ?
C21 H26 0.9900 . ?
C21 H27 0.9900 . ?
C22 C23 1.547(10) . ?
C22 H28 0.9900 . ?
C22 H29 0.9900 . ?
C23 C24 1.517(11) . ?
C23 H30 0.9900 . ?
C23 H31 0.9900 . ?
C24 H32 0.9800 . ?
C24 H33 0.9800 . ?
C24 H34 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O1 C1 118.6(4) . . ?
O1 C1 C2 106.8(5) . . ?
O1 C1 H1 110.4 . . ?
C2 C1 H1 110.4 . . ?
O1 C1 H2 110.4 . . ?
C2 C1 H2 110.4 . . ?
H1 C1 H2 108.6 . . ?
C1 C2 C3 114.1(5) . . ?
C1 C2 H3 108.7 . . ?
C3 C2 H3 108.7 . . ?
C1 C2 H4 108.7 . . ?
C3 C2 H4 108.7 . . ?
H3 C2 H4 107.6 . . ?
C2 C3 C4 114.8(5) . . ?
C2 C3 H5 108.6 . . ?
C4 C3 H5 108.6 . . ?
C2 C3 H6 108.6 . . ?
C4 C3 H6 108.6 . . ?
H5 C3 H6 107.6 . . ?
C3 C4 C5 113.7(5) . . ?
C3 C4 H7 108.8 . . ?
C5 C4 H7 108.8 . . ?
C3 C4 H8 108.8 . . ?
C5 C4 H8 108.8 . . ?
H7 C4 H8 107.7 . . ?
C4 C5 H9 109.5 . . ?
C4 C5 H10 109.5 . . ?
H9 C5 H10 109.5 . . ?
C4 C5 H11 109.5 . . ?
H9 C5 H11 109.5 . . ?
H10 C5 H11 109.5 . . ?
O1 C6 C15 116.0(5) . . ?
O1 C6 C7 121.3(5) . . ?
C15 C6 C7 122.8(5) . . ?
C8 C7 C6 119.5(5) . . ?
C8 C7 H12 120.3 . . ?
C6 C7 H12 120.3 . . ?
C7 C8 C9 120.4(5) . . ?
C7 C8 H13 119.8 . . ?
C9 C8 H13 119.8 . . ?
C14 C9 C8 120.8(5) . . ?
C14 C9 C10 119.9(5) . . ?
C8 C9 C10 119.3(5) . . ?
C11 C10 C9 120.4(6) . . ?
C11 C10 H14 119.8 . . ?
C9 C10 H14 119.8 . . ?
C10 C11 C12 120.0(5) . . ?
C10 C11 H15 120.0 . . ?
C12 C11 H15 120.0 . . ?
C13 C12 C11 120.9(6) . . ?
C13 C12 H16 119.6 . . ?
C11 C12 H16 119.6 . . ?
C12 C13 C14 120.6(5) . . ?
C12 C13 H17 119.7 . . ?
C14 C13 H17 119.7 . . ?
C9 C14 C13 118.2(5) . . ?
C9 C14 C15 118.9(5) . . ?
C13 C14 C15 122.9(5) . . ?
C6 C15 C16 116.9(5) . . ?
C6 C15 C14 117.6(5) . . ?
C16 C15 C14 125.5(5) . . ?
N1 C16 C15 123.5(5) . . ?
N1 C16 H18 118.3 . . ?
C15 C16 H18 118.3 . . ?
C16 N1 N2 117.5(4) . . ?
C17 N2 N1 118.0(4) . . ?
C17 N2 H19 124(4) . . ?
N1 N2 H19 117(4) . . ?
O2 C17 N2 120.5(5) . . ?
O2 C17 C18 122.0(5) . . ?
N2 C17 C18 117.5(5) . . ?
C19 C18 C17 115.0(5) . . ?
C19 C18 H20 108.5 . . ?
C17 C18 H20 108.5 . . ?
C19 C18 H21 108.5 . . ?
C17 C18 H21 108.5 . . ?
H20 C18 H21 107.5 . . ?
C18 C19 C20 111.7(5) . . ?
C18 C19 H22 109.3 . . ?
C20 C19 H22 109.3 . . ?
C18 C19 H23 109.3 . . ?
C20 C19 H23 109.3 . . ?
H22 C19 H23 107.9 . . ?
C19 C20 C21 113.0(5) . . ?
C19 C20 H24 109.0 . . ?
C21 C20 H24 109.0 . . ?
C19 C20 H25 109.0 . . ?
C21 C20 H25 109.0 . . ?
H24 C20 H25 107.8 . . ?
C22 C21 C20 112.9(5) . . ?
C22 C21 H26 109.0 . . ?
C20 C21 H26 109.0 . . ?
C22 C21 H27 109.0 . . ?
C20 C21 H27 109.0 . . ?
H26 C21 H27 107.8 . . ?
C21 C22 C23 112.8(6) . . ?
C21 C22 H28 109.0 . . ?
C23 C22 H28 109.0 . . ?
C21 C22 H29 109.0 . . ?
C23 C22 H29 109.0 . . ?
H28 C22 H29 107.8 . . ?
C24 C23 C22 113.4(7) . . ?
C24 C23 H30 108.9 . . ?
C22 C23 H30 108.9 . . ?
C24 C23 H31 108.9 . . ?
C22 C23 H31 108.9 . . ?
H30 C23 H31 107.7 . . ?
C23 C24 H32 109.5 . . ?
C23 C24 H33 109.5 . . ?
H32 C24 H33 109.5 . . ?
C23 C24 H34 109.5 . . ?
H32 C24 H34 109.5 . . ?
H33 C24 H34 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 O1 C1 C2 175.8(4) . . . . ?
O1 C1 C2 C3 -65.5(6) . . . . ?
C1 C2 C3 C4 -170.1(5) . . . . ?
C2 C3 C4 C5 176.3(5) . . . . ?
C1 O1 C6 C15 179.5(4) . . . . ?
C1 O1 C6 C7 0.8(7) . . . . ?
O1 C6 C7 C8 177.7(5) . . . . ?
C15 C6 C7 C8 -0.9(8) . . . . ?
C6 C7 C8 C9 1.3(8) . . . . ?
C7 C8 C9 C14 0.6(8) . . . . ?
C7 C8 C9 C10 -179.9(5) . . . . ?
C14 C9 C10 C11 1.3(8) . . . . ?
C8 C9 C10 C11 -178.3(5) . . . . ?
C9 C10 C11 C12 0.9(9) . . . . ?
C10 C11 C12 C13 -1.9(9) . . . . ?
C11 C12 C13 C14 0.6(9) . . . . ?
C8 C9 C14 C13 177.1(5) . . . . ?
C10 C9 C14 C13 -2.5(8) . . . . ?
C8 C9 C14 C15 -2.8(7) . . . . ?
C10 C9 C14 C15 177.6(5) . . . . ?
C12 C13 C14 C9 1.6(8) . . . . ?
C12 C13 C14 C15 -178.5(5) . . . . ?
O1 C6 C15 C16 0.7(7) . . . . ?
C7 C6 C15 C16 179.3(5) . . . . ?
O1 C6 C15 C14 180.0(4) . . . . ?
C7 C6 C15 C14 -1.4(8) . . . . ?
C9 C14 C15 C6 3.2(7) . . . . ?
C13 C14 C15 C6 -176.7(5) . . . . ?
C9 C14 C15 C16 -177.6(5) . . . . ?
C13 C14 C15 C16 2.5(8) . . . . ?
C6 C15 C16 N1 -172.1(5) . . . . ?
C14 C15 C16 N1 8.6(8) . . . . ?
C15 C16 N1 N2 179.9(5) . . . . ?
C16 N1 N2 C17 174.4(5) . . . . ?
N1 N2 C17 O2 -177.7(5) . . . . ?
N1 N2 C17 C18 0.3(7) . . . . ?
O2 C17 C18 C19 -1.5(7) . . . . ?
N2 C17 C18 C19 -179.4(4) . . . . ?
C17 C18 C19 C20 -178.0(4) . . . . ?
C18 C19 C20 C21 -172.9(4) . . . . ?
C19 C20 C21 C22 -179.7(5) . . . . ?
C20 C21 C22 C23 -168.3(6) . . . . ?
C21 C22 C23 C24 -59.8(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C16 H18 O2 0.95 2.45 3.262(6) 143.2 2_655 yes
N2 H19 O2 0.86(5) 2.11(6) 2.928(6) 157(5) 2_655 yes

_refine_diff_density_max         1.169
_refine_diff_density_min         -0.692
_refine_diff_density_rms         0.170



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
_exptl_crystal_preparation       photochromic
####################################################################### 
# 
# 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_E-c7-A
_database_code_depnum_ccdc_archive 'CCDC 2431298'
loop_
_audit_author_name
_audit_author_address
'Isao Yoshikawa'
;Institute of Industrial Science, The University of Tokyo
Japan
;
_audit_update_record             
;
2025-03-14 deposited with the CCDC.	2025-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H32 N2 O3'
_chemical_formula_sum            'C23 H32 N2 O3'
_chemical_formula_weight         384.50

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   11.2171(9)
_cell_length_b                   4.8288(3)
_cell_length_c                   38.442(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.782(8)
_cell_angle_gamma                90
_cell_volume                     2079.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3858
_cell_measurement_theta_min      4.1300
_cell_measurement_theta_max      71.9280

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.644
_shelx_estimated_absorpt_T_min   0.830
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_T_min  0.37609
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            19328
_diffrn_reflns_av_unetI/netI     0.0786
_diffrn_reflns_av_R_equivalents  0.1255
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         3.453
_diffrn_reflns_theta_max         73.248
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4144
_reflns_number_gt                2921
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'CrysAlisPro 1.171.41.107a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_refine_special_details          'Refined as a 2-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1922P)²+21.0362P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4144
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1845
_refine_ls_R_factor_gt           0.1579
_refine_ls_wR_factor_ref         0.4341
_refine_ls_wR_factor_gt          0.4175
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5445(9) -0.103(3) 0.5588(3) 0.067(4) Uani 1 1 d . . . . .
H1 H 0.480857 -0.220917 0.567281 0.101 Uiso 1 1 calc R U . . .
H2 H 0.609430 -0.090052 0.576761 0.101 Uiso 1 1 calc R U . . .
H3 H 0.512793 0.082044 0.553656 0.101 Uiso 1 1 calc R U . . .
C2 C 0.5913(8) -0.228(2) 0.5263(3) 0.051(3) Uani 1 1 d . . . . .
H4 H 0.623172 -0.415489 0.531248 0.062 Uiso 1 1 calc R U . . .
H5 H 0.526203 -0.242800 0.508063 0.062 Uiso 1 1 calc R U . . .
O1 O 0.6840(5) -0.0521(15) 0.51455(18) 0.0471(17) Uani 1 1 d . . . . .
C3 C 0.7435(8) -0.1761(19) 0.4872(2) 0.038(2) Uani 1 1 d . . . . .
H6 H 0.686651 -0.206852 0.467003 0.046 Uiso 1 1 calc R U . . .
H7 H 0.776185 -0.357831 0.494751 0.046 Uiso 1 1 calc R U . . .
C4 C 0.8432(7) 0.0100(17) 0.4767(2) 0.0334(19) Uani 1 1 d . . . . .
H8 H 0.874572 0.116680 0.497111 0.040 Uiso 1 1 calc R U . . .
H9 H 0.909029 -0.102882 0.467931 0.040 Uiso 1 1 calc R U . . .
O2 O 0.8001(5) 0.1926(11) 0.45049(16) 0.0333(14) Uani 1 1 d . . . . .
C5 C 0.8816(6) 0.3665(17) 0.4359(2) 0.0297(17) Uani 1 1 d . . . . .
C6 C 0.9988(7) 0.3940(17) 0.4508(2) 0.0342(19) Uani 1 1 d . . . . .
H10 H 1.025347 0.283841 0.470175 0.041 Uiso 1 1 calc R U . . .
C7 C 1.0741(7) 0.5877(18) 0.4363(2) 0.0332(18) Uani 1 1 d . . . . .
H11 H 1.152835 0.609623 0.446184 0.040 Uiso 1 1 calc R U . . .
C8 C 1.0373(6) 0.7495(17) 0.4079(2) 0.0309(18) Uani 1 1 d . . . . .
C9 C 1.1148(7) 0.9478(18) 0.3934(3) 0.037(2) Uani 1 1 d . . . . .
H12 H 1.192665 0.972745 0.403793 0.045 Uiso 1 1 calc R U . . .
C10 C 1.0804(7) 1.1006(19) 0.3655(2) 0.037(2) Uani 1 1 d . . . . .
H13 H 1.132860 1.235690 0.356820 0.045 Uiso 1 1 calc R U . . .
C11 C 0.9658(7) 1.0604(18) 0.3489(2) 0.0344(19) Uani 1 1 d . . . . .
H14 H 0.942954 1.163231 0.328583 0.041 Uiso 1 1 calc R U . . .
C12 C 0.8882(7) 0.8739(17) 0.3622(2) 0.0338(19) Uani 1 1 d . . . . .
H15 H 0.811353 0.852013 0.350975 0.041 Uiso 1 1 calc R U . . .
C13 C 0.9188(6) 0.7118(15) 0.3921(2) 0.0272(17) Uani 1 1 d . . . . .
C14 C 0.8421(6) 0.5157(15) 0.4074(2) 0.0259(17) Uani 1 1 d . . . . .
C15 C 0.7204(6) 0.4550(16) 0.3929(2) 0.0300(18) Uani 1 1 d . . . . .
H16 H 0.692591 0.269157 0.392481 0.036 Uiso 1 1 calc R U . . .
N1 N 0.6513(5) 0.6491(14) 0.38083(19) 0.0320(16) Uani 1 1 d . . . . .
N2 N 0.5412(5) 0.5539(13) 0.36724(19) 0.0310(16) Uani 1 1 d . . . . .
H17 H 0.525344 0.375433 0.366774 0.037 Uiso 1 1 calc R U . . .
C16 C 0.4594(6) 0.7373(15) 0.3548(2) 0.0261(16) Uani 1 1 d . . . . .
O3 O 0.4748(5) 0.9899(13) 0.35478(18) 0.0419(16) Uani 1 1 d . . . . .
C17 C 0.3433(6) 0.6087(15) 0.3420(2) 0.0308(18) Uani 1 1 d . . . . .
H18 H 0.286527 0.615487 0.360912 0.037 Uiso 1 1 calc R U . . .
H19 H 0.357343 0.411502 0.336482 0.037 Uiso 1 1 calc R U . . .
C18 C 0.2862(6) 0.7509(16) 0.3097(2) 0.0311(18) Uani 1 1 d . . . . .
H20 H 0.275308 0.950089 0.314760 0.037 Uiso 1 1 calc R U . . .
H21 H 0.340888 0.735825 0.290329 0.037 Uiso 1 1 calc R U . . .
C19 C 0.1654(6) 0.6246(17) 0.2983(2) 0.0316(18) Uani 1 1 d . . . . .
H22 H 0.176469 0.426271 0.292771 0.038 Uiso 1 1 calc R U . . .
H23 H 0.111095 0.636682 0.317779 0.038 Uiso 1 1 calc R U . . .
C20 C 0.1089(7) 0.7702(19) 0.2667(2) 0.0358(19) Uani 1 1 d . . . . .
H24 H 0.162116 0.750615 0.247096 0.043 Uiso 1 1 calc R U . . .
H25 H 0.102209 0.970131 0.272007 0.043 Uiso 1 1 calc R U . . .
C21 C -0.0142(7) 0.660(2) 0.2555(2) 0.041(2) Uani 1 1 d . . . . .
H26 H -0.008210 0.458578 0.251402 0.049 Uiso 1 1 calc R U . . .
H27 H -0.068430 0.688891 0.274693 0.049 Uiso 1 1 calc R U . . .
C22 C -0.0685(8) 0.795(2) 0.2229(3) 0.042(2) Uani 1 1 d . . . . .
H28 H -0.012608 0.772834 0.203985 0.051 Uiso 1 1 calc R U . . .
H29 H -0.077146 0.995673 0.227344 0.051 Uiso 1 1 calc R U . . .
C23 C -0.1890(8) 0.680(2) 0.2107(3) 0.049(3) Uani 1 1 d . . . . .
H30 H -0.217721 0.777977 0.189574 0.073 Uiso 1 1 calc R U . . .
H31 H -0.181273 0.482108 0.205549 0.073 Uiso 1 1 calc R U . . .
H32 H -0.245934 0.705369 0.228952 0.073 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.505(16) . ?
C1 H1 0.9800 . ?
C1 H2 0.9800 . ?
C1 H3 0.9800 . ?
C2 O1 1.431(10) . ?
C2 H4 0.9900 . ?
C2 H5 0.9900 . ?
O1 C3 1.408(11) . ?
C3 C4 1.505(12) . ?
C3 H6 0.9900 . ?
C3 H7 0.9900 . ?
C4 O2 1.406(10) . ?
C4 H8 0.9900 . ?
C4 H9 0.9900 . ?
O2 C5 1.380(9) . ?
C5 C14 1.368(11) . ?
C5 C6 1.414(10) . ?
C6 C7 1.395(12) . ?
C6 H10 0.9500 . ?
C7 C8 1.390(12) . ?
C7 H11 0.9500 . ?
C8 C9 1.424(11) . ?
C8 C13 1.445(10) . ?
C9 C10 1.344(13) . ?
C9 H12 0.9500 . ?
C10 C11 1.421(11) . ?
C10 H13 0.9500 . ?
C11 C12 1.368(12) . ?
C11 H14 0.9500 . ?
C12 C13 1.421(12) . ?
C12 H15 0.9500 . ?
C13 C14 1.425(10) . ?
C14 C15 1.478(10) . ?
C15 N1 1.288(10) . ?
C15 H16 0.9500 . ?
N1 N2 1.395(8) . ?
N2 C16 1.345(9) . ?
N2 H17 0.8800 . ?
C16 O3 1.232(10) . ?
C16 C17 1.505(10) . ?
C17 C18 1.531(12) . ?
C17 H18 0.9900 . ?
C17 H19 0.9900 . ?
C18 C19 1.530(10) . ?
C18 H20 0.9900 . ?
C18 H21 0.9900 . ?
C19 C20 1.515(12) . ?
C19 H22 0.9900 . ?
C19 H23 0.9900 . ?
C20 C21 1.522(11) . ?
C20 H24 0.9900 . ?
C20 H25 0.9900 . ?
C21 C22 1.510(13) . ?
C21 H26 0.9900 . ?
C21 H27 0.9900 . ?
C22 C23 1.515(12) . ?
C22 H28 0.9900 . ?
C22 H29 0.9900 . ?
C23 H30 0.9800 . ?
C23 H31 0.9800 . ?
C23 H32 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 109.5 . . ?
C2 C1 H2 109.5 . . ?
H1 C1 H2 109.5 . . ?
C2 C1 H3 109.5 . . ?
H1 C1 H3 109.5 . . ?
H2 C1 H3 109.5 . . ?
O1 C2 C1 108.3(9) . . ?
O1 C2 H4 110.0 . . ?
C1 C2 H4 110.0 . . ?
O1 C2 H5 110.0 . . ?
C1 C2 H5 110.0 . . ?
H4 C2 H5 108.4 . . ?
C3 O1 C2 111.2(8) . . ?
O1 C3 C4 109.4(7) . . ?
O1 C3 H6 109.8 . . ?
C4 C3 H6 109.8 . . ?
O1 C3 H7 109.8 . . ?
C4 C3 H7 109.8 . . ?
H6 C3 H7 108.2 . . ?
O2 C4 C3 109.4(7) . . ?
O2 C4 H8 109.8 . . ?
C3 C4 H8 109.8 . . ?
O2 C4 H9 109.8 . . ?
C3 C4 H9 109.8 . . ?
H8 C4 H9 108.2 . . ?
C5 O2 C4 117.4(6) . . ?
C14 C5 O2 116.8(6) . . ?
C14 C5 C6 122.3(7) . . ?
O2 C5 C6 120.9(8) . . ?
C7 C6 C5 118.0(8) . . ?
C7 C6 H10 121.0 . . ?
C5 C6 H10 121.0 . . ?
C8 C7 C6 121.9(7) . . ?
C8 C7 H11 119.0 . . ?
C6 C7 H11 119.0 . . ?
C7 C8 C9 121.4(7) . . ?
C7 C8 C13 119.4(7) . . ?
C9 C8 C13 119.1(8) . . ?
C10 C9 C8 121.6(8) . . ?
C10 C9 H12 119.2 . . ?
C8 C9 H12 119.2 . . ?
C9 C10 C11 120.2(8) . . ?
C9 C10 H13 119.9 . . ?
C11 C10 H13 119.9 . . ?
C12 C11 C10 120.1(8) . . ?
C12 C11 H14 120.0 . . ?
C10 C11 H14 120.0 . . ?
C11 C12 C13 122.1(8) . . ?
C11 C12 H15 119.0 . . ?
C13 C12 H15 119.0 . . ?
C12 C13 C14 124.9(7) . . ?
C12 C13 C8 116.9(7) . . ?
C14 C13 C8 118.2(7) . . ?
C5 C14 C13 120.1(7) . . ?
C5 C14 C15 117.1(7) . . ?
C13 C14 C15 122.8(7) . . ?
N1 C15 C14 121.3(7) . . ?
N1 C15 H16 119.3 . . ?
C14 C15 H16 119.3 . . ?
C15 N1 N2 113.7(7) . . ?
C16 N2 N1 119.5(6) . . ?
C16 N2 H17 120.3 . . ?
N1 N2 H17 120.3 . . ?
O3 C16 N2 124.0(7) . . ?
O3 C16 C17 121.8(7) . . ?
N2 C16 C17 114.2(6) . . ?
C16 C17 C18 113.7(7) . . ?
C16 C17 H18 108.8 . . ?
C18 C17 H18 108.8 . . ?
C16 C17 H19 108.8 . . ?
C18 C17 H19 108.8 . . ?
H18 C17 H19 107.7 . . ?
C19 C18 C17 112.5(7) . . ?
C19 C18 H20 109.1 . . ?
C17 C18 H20 109.1 . . ?
C19 C18 H21 109.1 . . ?
C17 C18 H21 109.1 . . ?
H20 C18 H21 107.8 . . ?
C20 C19 C18 112.0(7) . . ?
C20 C19 H22 109.2 . . ?
C18 C19 H22 109.2 . . ?
C20 C19 H23 109.2 . . ?
C18 C19 H23 109.2 . . ?
H22 C19 H23 107.9 . . ?
C19 C20 C21 113.9(7) . . ?
C19 C20 H24 108.8 . . ?
C21 C20 H24 108.8 . . ?
C19 C20 H25 108.8 . . ?
C21 C20 H25 108.8 . . ?
H24 C20 H25 107.7 . . ?
C22 C21 C20 114.2(8) . . ?
C22 C21 H26 108.7 . . ?
C20 C21 H26 108.7 . . ?
C22 C21 H27 108.7 . . ?
C20 C21 H27 108.7 . . ?
H26 C21 H27 107.6 . . ?
C21 C22 C23 114.7(8) . . ?
C21 C22 H28 108.6 . . ?
C23 C22 H28 108.6 . . ?
C21 C22 H29 108.6 . . ?
C23 C22 H29 108.6 . . ?
H28 C22 H29 107.6 . . ?
C22 C23 H30 109.5 . . ?
C22 C23 H31 109.5 . . ?
H30 C23 H31 109.5 . . ?
C22 C23 H32 109.5 . . ?
H30 C23 H32 109.5 . . ?
H31 C23 H32 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 O1 C3 171.5(9) . . . . ?
C2 O1 C3 C4 -177.7(8) . . . . ?
O1 C3 C4 O2 -90.0(9) . . . . ?
C3 C4 O2 C5 -175.6(7) . . . . ?
C4 O2 C5 C14 171.3(7) . . . . ?
C4 O2 C5 C6 -10.8(11) . . . . ?
C14 C5 C6 C7 2.2(13) . . . . ?
O2 C5 C6 C7 -175.5(7) . . . . ?
C5 C6 C7 C8 -0.5(13) . . . . ?
C6 C7 C8 C9 179.6(8) . . . . ?
C6 C7 C8 C13 -1.8(12) . . . . ?
C7 C8 C9 C10 178.6(9) . . . . ?
C13 C8 C9 C10 0.0(13) . . . . ?
C8 C9 C10 C11 -2.1(14) . . . . ?
C9 C10 C11 C12 2.6(14) . . . . ?
C10 C11 C12 C13 -1.1(13) . . . . ?
C11 C12 C13 C14 179.5(8) . . . . ?
C11 C12 C13 C8 -0.9(12) . . . . ?
C7 C8 C13 C12 -177.2(8) . . . . ?
C9 C8 C13 C12 1.4(11) . . . . ?
C7 C8 C13 C14 2.5(11) . . . . ?
C9 C8 C13 C14 -178.9(7) . . . . ?
O2 C5 C14 C13 176.3(7) . . . . ?
C6 C5 C14 C13 -1.5(12) . . . . ?
O2 C5 C14 C15 -6.0(11) . . . . ?
C6 C5 C14 C15 176.2(8) . . . . ?
C12 C13 C14 C5 178.8(8) . . . . ?
C8 C13 C14 C5 -0.8(11) . . . . ?
C12 C13 C14 C15 1.2(12) . . . . ?
C8 C13 C14 C15 -178.4(7) . . . . ?
C5 C14 C15 N1 142.2(8) . . . . ?
C13 C14 C15 N1 -40.2(12) . . . . ?
C14 C15 N1 N2 178.1(7) . . . . ?
C15 N1 N2 C16 177.9(8) . . . . ?
N1 N2 C16 O3 -0.4(13) . . . . ?
N1 N2 C16 C17 -178.2(7) . . . . ?
O3 C16 C17 C18 39.0(12) . . . . ?
N2 C16 C17 C18 -143.2(7) . . . . ?
C16 C17 C18 C19 -177.2(7) . . . . ?
C17 C18 C19 C20 179.0(7) . . . . ?
C18 C19 C20 C21 -177.3(7) . . . . ?
C19 C20 C21 C22 -177.1(8) . . . . ?
C20 C21 C22 C23 177.8(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H17 O3 0.88 1.99 2.858(9) 166.9 1_545 yes
C17 H19 O3 0.99 2.51 3.358(9) 143.9 1_545 yes

_refine_diff_density_max         0.856
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.130



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
_exptl_crystal_preparation       photochromic
####################################################################### 
# 
# 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_Z-d7
_database_code_depnum_ccdc_archive 'CCDC 2431301'
loop_
_audit_author_name
_audit_author_address
'Isao Yoshikawa'
;Institute of Industrial Science, The University of Tokyo
Japan
;
_audit_update_record             
;
2025-03-14 deposited with the CCDC.	2025-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H30 N2 O4'
_chemical_formula_sum            'C23 H30 N2 O4'
_chemical_formula_weight         398.49

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.2378(4)
_cell_length_b                   13.9123(4)
_cell_length_c                   18.4427(6)
_cell_angle_alpha                87.269(2)
_cell_angle_beta                 81.750(3)
_cell_angle_gamma                88.914(3)
_cell_volume                     2089.25(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10180
_cell_measurement_theta_min      3.9620
_cell_measurement_theta_max      72.3190

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.060
_shelx_estimated_absorpt_T_min   0.850
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_coefficient_mu    0.692
_exptl_absorpt_correction_T_min  0.798
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            23125
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.180
_diffrn_reflns_theta_max         72.844
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             8010
_reflns_number_gt                6578
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.41.107a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0841P)²+1.3784P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8010
_refine_ls_number_parameters     533
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1712
_refine_ls_wR_factor_gt          0.1652
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.08611(17) 0.04331(10) 0.10281(8) 0.0299(3) Uani 1 1 d . . . . .
C1 C 0.1370(3) -0.04224(15) 0.14057(12) 0.0320(5) Uani 1 1 d . . . . .
H1 H 0.249750 -0.034527 0.151986 0.038 Uiso 1 1 calc R U . . .
H2 H 0.136794 -0.098005 0.109188 0.038 Uiso 1 1 calc R U . . .
C2 C 0.0209(3) -0.05893(17) 0.20984(12) 0.0356(5) Uani 1 1 d . . . . .
H3 H -0.092602 -0.047450 0.199355 0.043 Uiso 1 1 calc R U . . .
H4 H 0.029908 -0.127094 0.226968 0.043 Uiso 1 1 calc R U . . .
O2 O 0.05027(18) 0.00160(11) 0.26753(8) 0.0343(3) Uani 1 1 d . . . . .
C3 C 0.1658(3) -0.03140(16) 0.30737(12) 0.0338(5) Uani 1 1 d . . . . .
O3 O 0.2489(2) -0.10178(12) 0.29326(9) 0.0406(4) Uani 1 1 d . . . . .
C4 C 0.1759(4) 0.0302(2) 0.37022(14) 0.0474(6) Uani 1 1 d . . . . .
H5 H 0.240192 -0.003223 0.404685 0.071 Uiso 1 1 calc R U . . .
H6 H 0.065114 0.043593 0.395184 0.071 Uiso 1 1 calc R U . . .
H7 H 0.228987 0.090924 0.352208 0.071 Uiso 1 1 calc R U . . .
C5 C 0.1644(2) 0.06232(15) 0.03363(11) 0.0275(4) Uani 1 1 d . . . . .
C6 C 0.2880(3) 0.00178(15) -0.00110(12) 0.0304(4) Uani 1 1 d . . . . .
H8 H 0.322145 -0.053879 0.024837 0.036 Uiso 1 1 calc R U . . .
C7 C 0.3589(3) 0.02200(16) -0.07115(12) 0.0313(5) Uani 1 1 d . . . . .
H9 H 0.440820 -0.020302 -0.093697 0.038 Uiso 1 1 calc R U . . .
C8 C 0.3129(2) 0.10505(15) -0.11119(11) 0.0292(4) Uani 1 1 d . . . . .
C9 C 0.3889(3) 0.12701(17) -0.18349(12) 0.0330(5) Uani 1 1 d . . . . .
H10 H 0.471814 0.085383 -0.206160 0.040 Uiso 1 1 calc R U . . .
C10 C 0.3439(3) 0.20781(17) -0.22094(12) 0.0361(5) Uani 1 1 d . . . . .
H11 H 0.395690 0.222557 -0.269505 0.043 Uiso 1 1 calc R U . . .
C11 C 0.2208(3) 0.26913(17) -0.18756(12) 0.0346(5) Uani 1 1 d . . . . .
H12 H 0.189769 0.325081 -0.214088 0.042 Uiso 1 1 calc R U . . .
C12 C 0.1449(3) 0.24986(15) -0.11773(11) 0.0305(4) Uani 1 1 d . . . . .
H13 H 0.061957 0.292422 -0.096349 0.037 Uiso 1 1 calc R U . . .
C13 C 0.1889(2) 0.16646(15) -0.07658(11) 0.0283(4) Uani 1 1 d . . . . .
C14 C 0.1138(2) 0.14427(15) -0.00320(11) 0.0272(4) Uani 1 1 d . . . . .
C15 C -0.0275(2) 0.20330(15) 0.02857(11) 0.0291(4) Uani 1 1 d . . . . .
H14 H -0.114381 0.208351 -0.000234 0.035 Uiso 1 1 calc R U . . .
N1 N -0.0538(2) 0.24870(12) 0.08778(9) 0.0286(4) Uani 1 1 d . . . . .
N2 N 0.0637(2) 0.24686(13) 0.13316(9) 0.0276(4) Uani 1 1 d . . . . .
H15 H 0.153(3) 0.217(2) 0.1216(15) 0.041 Uiso 1 1 d . U . . .
C16 C 0.0428(3) 0.30498(14) 0.19145(11) 0.0288(4) Uani 1 1 d . . . . .
O4 O -0.07771(18) 0.35708(10) 0.20489(8) 0.0327(3) Uani 1 1 d . . . . .
C17 C 0.1820(3) 0.29987(17) 0.23641(12) 0.0338(5) Uani 1 1 d . . . . .
H16 H 0.279579 0.329890 0.207082 0.041 Uiso 1 1 calc R U . . .
H17 H 0.209425 0.231368 0.246347 0.041 Uiso 1 1 calc R U . . .
C18 C 0.1464(3) 0.34885(16) 0.30905(12) 0.0336(5) Uani 1 1 d . . . . .
H18 H 0.248480 0.348571 0.331603 0.040 Uiso 1 1 calc R U . . .
H19 H 0.115980 0.416874 0.299046 0.040 Uiso 1 1 calc R U . . .
C19 C 0.0115(3) 0.30373(17) 0.36416(12) 0.0360(5) Uani 1 1 d . . . . .
H20 H 0.034724 0.233983 0.370369 0.043 Uiso 1 1 calc R U . . .
H21 H -0.094121 0.311241 0.344646 0.043 Uiso 1 1 calc R U . . .
C20 C -0.0048(3) 0.34833(18) 0.43855(12) 0.0381(5) Uani 1 1 d . . . . .
H22 H 0.097395 0.335581 0.459974 0.046 Uiso 1 1 calc R U . . .
H23 H -0.017561 0.418935 0.431646 0.046 Uiso 1 1 calc R U . . .
C21 C -0.1487(3) 0.31032(18) 0.49198(12) 0.0383(5) Uani 1 1 d . . . . .
H24 H -0.131199 0.240541 0.501571 0.046 Uiso 1 1 calc R U . . .
H25 H -0.249336 0.318200 0.468607 0.046 Uiso 1 1 calc R U . . .
C22 C -0.1766(3) 0.35895(19) 0.56504(13) 0.0429(6) Uani 1 1 d . . . . .
H26 H -0.075670 0.352427 0.588345 0.052 Uiso 1 1 calc R U . . .
H27 H -0.197925 0.428447 0.556024 0.052 Uiso 1 1 calc R U . . .
C23 C -0.3180(3) 0.3170(2) 0.61682(14) 0.0478(6) Uani 1 1 d . . . . .
H28 H -0.417156 0.320107 0.593090 0.072 Uiso 1 1 calc R U . . .
H29 H -0.335955 0.353695 0.661366 0.072 Uiso 1 1 calc R U . . .
H30 H -0.292929 0.249694 0.629736 0.072 Uiso 1 1 calc R U . . .
O5 O 0.56215(18) 0.42785(10) 0.12872(8) 0.0312(3) Uani 1 1 d . . . . .
C24 C 0.6190(3) 0.49214(15) 0.17777(12) 0.0315(5) Uani 1 1 d . . . . .
H31 H 0.581835 0.558822 0.167388 0.038 Uiso 1 1 calc R U . . .
H32 H 0.740301 0.490807 0.172350 0.038 Uiso 1 1 calc R U . . .
C25 C 0.5473(3) 0.45762(16) 0.25385(12) 0.0349(5) Uani 1 1 d . . . . .
H33 H 0.426992 0.468302 0.262056 0.042 Uiso 1 1 calc R U . . .
H34 H 0.570746 0.388209 0.262011 0.042 Uiso 1 1 calc R U . . .
O6 O 0.6262(2) 0.51417(11) 0.30183(8) 0.0386(4) Uani 1 1 d . . . . .
C26 C 0.5896(3) 0.49096(17) 0.37355(13) 0.0411(5) Uani 1 1 d . . . . .
O7 O 0.4937(3) 0.42958(13) 0.39776(10) 0.0532(5) Uani 1 1 d . . . . .
C27 C 0.6848(4) 0.5501(2) 0.41777(16) 0.0550(7) Uani 1 1 d . . . . .
H35 H 0.626697 0.552774 0.467887 0.083 Uiso 1 1 calc R U . . .
H36 H 0.696456 0.615447 0.395490 0.083 Uiso 1 1 calc R U . . .
H37 H 0.793664 0.520975 0.418941 0.083 Uiso 1 1 calc R U . . .
C28 C 0.6382(2) 0.43162(15) 0.05829(11) 0.0276(4) Uani 1 1 d . . . . .
C29 C 0.7490(3) 0.50496(15) 0.03031(12) 0.0310(4) Uani 1 1 d . . . . .
H38 H 0.774449 0.553044 0.061639 0.037 Uiso 1 1 calc R U . . .
C30 C 0.8196(3) 0.50750(15) -0.04104(12) 0.0322(5) Uani 1 1 d . . . . .
H39 H 0.893091 0.557836 -0.058942 0.039 Uiso 1 1 calc R U . . .
C31 C 0.7858(3) 0.43667(15) -0.08912(11) 0.0290(4) Uani 1 1 d . . . . .
C32 C 0.8599(3) 0.43746(16) -0.16286(12) 0.0337(5) Uani 1 1 d . . . . .
H40 H 0.933974 0.487266 -0.181353 0.040 Uiso 1 1 calc R U . . .
C33 C 0.8271(3) 0.36794(17) -0.20815(12) 0.0346(5) Uani 1 1 d . . . . .
H41 H 0.878244 0.369401 -0.257749 0.042 Uiso 1 1 calc R U . . .
C34 C 0.7177(3) 0.29421(16) -0.18130(12) 0.0333(5) Uani 1 1 d . . . . .
H42 H 0.695324 0.245692 -0.212918 0.040 Uiso 1 1 calc R U . . .
C35 C 0.6429(3) 0.29148(15) -0.11021(11) 0.0300(4) Uani 1 1 d . . . . .
H43 H 0.569187 0.240969 -0.093082 0.036 Uiso 1 1 calc R U . . .
C36 C 0.6735(2) 0.36283(14) -0.06134(11) 0.0277(4) Uani 1 1 d . . . . .
C37 C 0.5987(2) 0.36127(14) 0.01320(11) 0.0274(4) Uani 1 1 d . . . . .
C38 C 0.4684(2) 0.29043(15) 0.03791(11) 0.0284(4) Uani 1 1 d . . . . .
H44 H 0.383489 0.290456 0.008072 0.034 Uiso 1 1 calc R U . . .
N3 N 0.4497(2) 0.22904(12) 0.09241(9) 0.0281(4) Uani 1 1 d . . . . .
N4 N 0.5687(2) 0.22194(12) 0.13705(9) 0.0280(4) Uani 1 1 d . . . . .
H45 H 0.661(3) 0.2550(19) 0.1253(15) 0.042 Uiso 1 1 d . U . . .
C39 C 0.5525(3) 0.15639(14) 0.19490(11) 0.0288(4) Uani 1 1 d . . . . .
O8 O 0.43224(18) 0.10508(10) 0.21081(8) 0.0328(3) Uani 1 1 d . . . . .
C40 C 0.6989(3) 0.15200(16) 0.23552(12) 0.0336(5) Uani 1 1 d . . . . .
H46 H 0.741930 0.217786 0.236667 0.040 Uiso 1 1 calc R U . . .
H47 H 0.786064 0.112336 0.208302 0.040 Uiso 1 1 calc R U . . .
C41 C 0.6608(3) 0.11030(16) 0.31369(12) 0.0349(5) Uani 1 1 d . . . . .
H48 H 0.605415 0.047861 0.313142 0.042 Uiso 1 1 calc R U . . .
H49 H 0.765056 0.097939 0.333560 0.042 Uiso 1 1 calc R U . . .
C42 C 0.5526(3) 0.17602(16) 0.36402(12) 0.0345(5) Uani 1 1 d . . . . .
H50 H 0.449013 0.189069 0.343783 0.041 Uiso 1 1 calc R U . . .
H51 H 0.608689 0.238158 0.365047 0.041 Uiso 1 1 calc R U . . .
C43 C 0.5126(3) 0.13395(17) 0.44199(12) 0.0363(5) Uani 1 1 d . . . . .
H52 H 0.482883 0.065595 0.440036 0.044 Uiso 1 1 calc R U . . .
H53 H 0.612361 0.135772 0.466072 0.044 Uiso 1 1 calc R U . . .
C44 C 0.3744(3) 0.18530(18) 0.48867(12) 0.0405(5) Uani 1 1 d . . . . .
H54 H 0.277367 0.188882 0.462570 0.049 Uiso 1 1 calc R U . . .
H55 H 0.408248 0.251982 0.494818 0.049 Uiso 1 1 calc R U . . .
C45 C 0.3258(3) 0.1363(2) 0.56433(13) 0.0482(6) Uani 1 1 d . . . . .
H56 H 0.310820 0.066912 0.558179 0.058 Uiso 1 1 calc R U . . .
H57 H 0.417406 0.142379 0.593099 0.058 Uiso 1 1 calc R U . . .
C46 C 0.1729(4) 0.1753(2) 0.60751(16) 0.0569(7) Uani 1 1 d . . . . .
H58 H 0.186669 0.243733 0.615024 0.085 Uiso 1 1 calc R U . . .
H59 H 0.151823 0.140137 0.655181 0.085 Uiso 1 1 calc R U . . .
H60 H 0.080027 0.167438 0.580602 0.085 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.361(2) . ?
O1 C1 1.436(3) . ?
C1 C2 1.494(3) . ?
C1 H1 0.9900 . ?
C1 H2 0.9900 . ?
C2 O2 1.438(3) . ?
C2 H3 0.9900 . ?
C2 H4 0.9900 . ?
O2 C3 1.345(3) . ?
C3 O3 1.201(3) . ?
C3 C4 1.487(3) . ?
C4 H5 0.9800 . ?
C4 H6 0.9800 . ?
C4 H7 0.9800 . ?
C5 C14 1.387(3) . ?
C5 C6 1.410(3) . ?
C6 C7 1.358(3) . ?
C6 H8 0.9500 . ?
C7 C8 1.417(3) . ?
C7 H9 0.9500 . ?
C8 C9 1.412(3) . ?
C8 C13 1.418(3) . ?
C9 C10 1.365(3) . ?
C9 H10 0.9500 . ?
C10 C11 1.405(3) . ?
C10 H11 0.9500 . ?
C11 C12 1.365(3) . ?
C11 H12 0.9500 . ?
C12 C13 1.426(3) . ?
C12 H13 0.9500 . ?
C13 C14 1.427(3) . ?
C14 C15 1.479(3) . ?
C15 N1 1.277(3) . ?
C15 H14 0.9500 . ?
N1 N2 1.367(2) . ?
N2 C16 1.365(3) . ?
N2 H15 0.84(3) . ?
C16 O4 1.221(3) . ?
C16 C17 1.507(3) . ?
C17 C18 1.520(3) . ?
C17 H16 0.9900 . ?
C17 H17 0.9900 . ?
C18 C19 1.518(3) . ?
C18 H18 0.9900 . ?
C18 H19 0.9900 . ?
C19 C20 1.520(3) . ?
C19 H20 0.9900 . ?
C19 H21 0.9900 . ?
C20 C21 1.514(3) . ?
C20 H22 0.9900 . ?
C20 H23 0.9900 . ?
C21 C22 1.523(3) . ?
C21 H24 0.9900 . ?
C21 H25 0.9900 . ?
C22 C23 1.504(4) . ?
C22 H26 0.9900 . ?
C22 H27 0.9900 . ?
C23 H28 0.9800 . ?
C23 H29 0.9800 . ?
C23 H30 0.9800 . ?
O5 C28 1.358(2) . ?
O5 C24 1.432(2) . ?
C24 C25 1.502(3) . ?
C24 H31 0.9900 . ?
C24 H32 0.9900 . ?
C25 O6 1.441(3) . ?
C25 H33 0.9900 . ?
C25 H34 0.9900 . ?
O6 C26 1.339(3) . ?
C26 O7 1.200(3) . ?
C26 C27 1.493(4) . ?
C27 H35 0.9800 . ?
C27 H36 0.9800 . ?
C27 H37 0.9800 . ?
C28 C37 1.386(3) . ?
C28 C29 1.411(3) . ?
C29 C30 1.359(3) . ?
C29 H38 0.9500 . ?
C30 C31 1.414(3) . ?
C30 H39 0.9500 . ?
C31 C32 1.408(3) . ?
C31 C36 1.423(3) . ?
C32 C33 1.363(3) . ?
C32 H40 0.9500 . ?
C33 C34 1.403(3) . ?
C33 H41 0.9500 . ?
C34 C35 1.365(3) . ?
C34 H42 0.9500 . ?
C35 C36 1.422(3) . ?
C35 H43 0.9500 . ?
C36 C37 1.423(3) . ?
C37 C38 1.479(3) . ?
C38 N3 1.281(3) . ?
C38 H44 0.9500 . ?
N3 N4 1.367(2) . ?
N4 C39 1.363(3) . ?
N4 H45 0.89(3) . ?
C39 O8 1.225(2) . ?
C39 C40 1.507(3) . ?
C40 C41 1.520(3) . ?
C40 H46 0.9900 . ?
C40 H47 0.9900 . ?
C41 C42 1.518(3) . ?
C41 H48 0.9900 . ?
C41 H49 0.9900 . ?
C42 C43 1.520(3) . ?
C42 H50 0.9900 . ?
C42 H51 0.9900 . ?
C43 C44 1.514(3) . ?
C43 H52 0.9900 . ?
C43 H53 0.9900 . ?
C44 C45 1.527(3) . ?
C44 H54 0.9900 . ?
C44 H55 0.9900 . ?
C45 C46 1.497(4) . ?
C45 H56 0.9900 . ?
C45 H57 0.9900 . ?
C46 H58 0.9800 . ?
C46 H59 0.9800 . ?
C46 H60 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C1 116.64(16) . . ?
O1 C1 C2 108.63(18) . . ?
O1 C1 H1 110.0 . . ?
C2 C1 H1 110.0 . . ?
O1 C1 H2 110.0 . . ?
C2 C1 H2 110.0 . . ?
H1 C1 H2 108.3 . . ?
O2 C2 C1 113.42(18) . . ?
O2 C2 H3 108.9 . . ?
C1 C2 H3 108.9 . . ?
O2 C2 H4 108.9 . . ?
C1 C2 H4 108.9 . . ?
H3 C2 H4 107.7 . . ?
C3 O2 C2 114.95(17) . . ?
O3 C3 O2 123.6(2) . . ?
O3 C3 C4 125.2(2) . . ?
O2 C3 C4 111.2(2) . . ?
C3 C4 H5 109.5 . . ?
C3 C4 H6 109.5 . . ?
H5 C4 H6 109.5 . . ?
C3 C4 H7 109.5 . . ?
H5 C4 H7 109.5 . . ?
H6 C4 H7 109.5 . . ?
O1 C5 C14 116.67(18) . . ?
O1 C5 C6 122.94(19) . . ?
C14 C5 C6 120.37(19) . . ?
C7 C6 C5 120.9(2) . . ?
C7 C6 H8 119.6 . . ?
C5 C6 H8 119.6 . . ?
C6 C7 C8 121.2(2) . . ?
C6 C7 H9 119.4 . . ?
C8 C7 H9 119.4 . . ?
C9 C8 C7 121.1(2) . . ?
C9 C8 C13 120.6(2) . . ?
C7 C8 C13 118.32(19) . . ?
C10 C9 C8 120.3(2) . . ?
C10 C9 H10 119.9 . . ?
C8 C9 H10 119.9 . . ?
C9 C10 C11 119.9(2) . . ?
C9 C10 H11 120.1 . . ?
C11 C10 H11 120.1 . . ?
C12 C11 C10 121.3(2) . . ?
C12 C11 H12 119.4 . . ?
C10 C11 H12 119.4 . . ?
C11 C12 C13 120.6(2) . . ?
C11 C12 H13 119.7 . . ?
C13 C12 H13 119.7 . . ?
C8 C13 C12 117.42(19) . . ?
C8 C13 C14 120.20(19) . . ?
C12 C13 C14 122.37(19) . . ?
C5 C14 C13 119.07(18) . . ?
C5 C14 C15 121.61(18) . . ?
C13 C14 C15 118.99(18) . . ?
N1 C15 C14 131.54(19) . . ?
N1 C15 H14 114.2 . . ?
C14 C15 H14 114.2 . . ?
C15 N1 N2 119.14(18) . . ?
C16 N2 N1 118.36(18) . . ?
C16 N2 H15 120.9(18) . . ?
N1 N2 H15 120.1(18) . . ?
O4 C16 N2 122.4(2) . . ?
O4 C16 C17 123.52(18) . . ?
N2 C16 C17 114.04(18) . . ?
C16 C17 C18 114.49(18) . . ?
C16 C17 H16 108.6 . . ?
C18 C17 H16 108.6 . . ?
C16 C17 H17 108.6 . . ?
C18 C17 H17 108.6 . . ?
H16 C17 H17 107.6 . . ?
C19 C18 C17 115.27(18) . . ?
C19 C18 H18 108.5 . . ?
C17 C18 H18 108.5 . . ?
C19 C18 H19 108.5 . . ?
C17 C18 H19 108.5 . . ?
H18 C18 H19 107.5 . . ?
C18 C19 C20 112.79(19) . . ?
C18 C19 H20 109.0 . . ?
C20 C19 H20 109.0 . . ?
C18 C19 H21 109.0 . . ?
C20 C19 H21 109.0 . . ?
H20 C19 H21 107.8 . . ?
C21 C20 C19 113.37(19) . . ?
C21 C20 H22 108.9 . . ?
C19 C20 H22 108.9 . . ?
C21 C20 H23 108.9 . . ?
C19 C20 H23 108.9 . . ?
H22 C20 H23 107.7 . . ?
C20 C21 C22 114.8(2) . . ?
C20 C21 H24 108.6 . . ?
C22 C21 H24 108.6 . . ?
C20 C21 H25 108.6 . . ?
C22 C21 H25 108.6 . . ?
H24 C21 H25 107.6 . . ?
C23 C22 C21 112.7(2) . . ?
C23 C22 H26 109.1 . . ?
C21 C22 H26 109.1 . . ?
C23 C22 H27 109.1 . . ?
C21 C22 H27 109.1 . . ?
H26 C22 H27 107.8 . . ?
C22 C23 H28 109.5 . . ?
C22 C23 H29 109.5 . . ?
H28 C23 H29 109.5 . . ?
C22 C23 H30 109.5 . . ?
H28 C23 H30 109.5 . . ?
H29 C23 H30 109.5 . . ?
C28 O5 C24 117.00(16) . . ?
O5 C24 C25 106.35(17) . . ?
O5 C24 H31 110.5 . . ?
C25 C24 H31 110.5 . . ?
O5 C24 H32 110.5 . . ?
C25 C24 H32 110.5 . . ?
H31 C24 H32 108.7 . . ?
O6 C25 C24 104.81(17) . . ?
O6 C25 H33 110.8 . . ?
C24 C25 H33 110.8 . . ?
O6 C25 H34 110.8 . . ?
C24 C25 H34 110.8 . . ?
H33 C25 H34 108.9 . . ?
C26 O6 C25 115.57(18) . . ?
O7 C26 O6 123.4(2) . . ?
O7 C26 C27 125.5(2) . . ?
O6 C26 C27 111.1(2) . . ?
C26 C27 H35 109.5 . . ?
C26 C27 H36 109.5 . . ?
H35 C27 H36 109.5 . . ?
C26 C27 H37 109.5 . . ?
H35 C27 H37 109.5 . . ?
H36 C27 H37 109.5 . . ?
O5 C28 C37 117.11(18) . . ?
O5 C28 C29 122.44(18) . . ?
C37 C28 C29 120.42(19) . . ?
C30 C29 C28 120.66(19) . . ?
C30 C29 H38 119.7 . . ?
C28 C29 H38 119.7 . . ?
C29 C30 C31 121.26(19) . . ?
C29 C30 H39 119.4 . . ?
C31 C30 H39 119.4 . . ?
C32 C31 C30 121.96(19) . . ?
C32 C31 C36 119.70(19) . . ?
C30 C31 C36 118.34(19) . . ?
C33 C32 C31 121.1(2) . . ?
C33 C32 H40 119.5 . . ?
C31 C32 H40 119.5 . . ?
C32 C33 C34 119.8(2) . . ?
C32 C33 H41 120.1 . . ?
C34 C33 H41 120.1 . . ?
C35 C34 C33 120.7(2) . . ?
C35 C34 H42 119.7 . . ?
C33 C34 H42 119.7 . . ?
C34 C35 C36 121.20(19) . . ?
C34 C35 H43 119.4 . . ?
C36 C35 H43 119.4 . . ?
C35 C36 C31 117.51(19) . . ?
C35 C36 C37 122.44(18) . . ?
C31 C36 C37 120.03(18) . . ?
C28 C37 C36 119.27(18) . . ?
C28 C37 C38 121.94(18) . . ?
C36 C37 C38 118.48(18) . . ?
N3 C38 C37 131.43(19) . . ?
N3 C38 H44 114.3 . . ?
C37 C38 H44 114.3 . . ?
C38 N3 N4 118.31(17) . . ?
C39 N4 N3 119.40(17) . . ?
C39 N4 H45 120.5(17) . . ?
N3 N4 H45 119.8(17) . . ?
O8 C39 N4 123.0(2) . . ?
O8 C39 C40 123.86(19) . . ?
N4 C39 C40 113.16(17) . . ?
C39 C40 C41 113.54(18) . . ?
C39 C40 H46 108.9 . . ?
C41 C40 H46 108.9 . . ?
C39 C40 H47 108.9 . . ?
C41 C40 H47 108.9 . . ?
H46 C40 H47 107.7 . . ?
C42 C41 C40 113.03(19) . . ?
C42 C41 H48 109.0 . . ?
C40 C41 H48 109.0 . . ?
C42 C41 H49 109.0 . . ?
C40 C41 H49 109.0 . . ?
H48 C41 H49 107.8 . . ?
C41 C42 C43 113.14(19) . . ?
C41 C42 H50 109.0 . . ?
C43 C42 H50 109.0 . . ?
C41 C42 H51 109.0 . . ?
C43 C42 H51 109.0 . . ?
H50 C42 H51 107.8 . . ?
C44 C43 C42 114.5(2) . . ?
C44 C43 H52 108.6 . . ?
C42 C43 H52 108.6 . . ?
C44 C43 H53 108.6 . . ?
C42 C43 H53 108.6 . . ?
H52 C43 H53 107.6 . . ?
C43 C44 C45 113.5(2) . . ?
C43 C44 H54 108.9 . . ?
C45 C44 H54 108.9 . . ?
C43 C44 H55 108.9 . . ?
C45 C44 H55 108.9 . . ?
H54 C44 H55 107.7 . . ?
C46 C45 C44 115.2(2) . . ?
C46 C45 H56 108.5 . . ?
C44 C45 H56 108.5 . . ?
C46 C45 H57 108.5 . . ?
C44 C45 H57 108.5 . . ?
H56 C45 H57 107.5 . . ?
C45 C46 H58 109.5 . . ?
C45 C46 H59 109.5 . . ?
H58 C46 H59 109.5 . . ?
C45 C46 H60 109.5 . . ?
H58 C46 H60 109.5 . . ?
H59 C46 H60 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 O1 C1 C2 -171.19(16) . . . . ?
O1 C1 C2 O2 -78.3(2) . . . . ?
C1 C2 O2 C3 -84.5(2) . . . . ?
C2 O2 C3 O3 5.8(3) . . . . ?
C2 O2 C3 C4 -174.15(18) . . . . ?
C1 O1 C5 C14 179.21(17) . . . . ?
C1 O1 C5 C6 0.9(3) . . . . ?
O1 C5 C6 C7 177.77(18) . . . . ?
C14 C5 C6 C7 -0.5(3) . . . . ?
C5 C6 C7 C8 0.9(3) . . . . ?
C6 C7 C8 C9 178.73(19) . . . . ?
C6 C7 C8 C13 -0.7(3) . . . . ?
C7 C8 C9 C10 -179.42(19) . . . . ?
C13 C8 C9 C10 0.0(3) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C9 C10 C11 C12 0.3(3) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
C9 C8 C13 C12 0.3(3) . . . . ?
C7 C8 C13 C12 179.74(17) . . . . ?
C9 C8 C13 C14 -179.35(18) . . . . ?
C7 C8 C13 C14 0.1(3) . . . . ?
C11 C12 C13 C8 -0.3(3) . . . . ?
C11 C12 C13 C14 179.33(19) . . . . ?
O1 C5 C14 C13 -178.49(17) . . . . ?
C6 C5 C14 C13 -0.1(3) . . . . ?
O1 C5 C14 C15 -5.2(3) . . . . ?
C6 C5 C14 C15 173.20(18) . . . . ?
C8 C13 C14 C5 0.3(3) . . . . ?
C12 C13 C14 C5 -179.31(18) . . . . ?
C8 C13 C14 C15 -173.20(17) . . . . ?
C12 C13 C14 C15 7.2(3) . . . . ?
C5 C14 C15 N1 60.1(3) . . . . ?
C13 C14 C15 N1 -126.5(2) . . . . ?
C14 C15 N1 N2 0.5(3) . . . . ?
C15 N1 N2 C16 172.14(18) . . . . ?
N1 N2 C16 O4 1.1(3) . . . . ?
N1 N2 C16 C17 -178.05(17) . . . . ?
O4 C16 C17 C18 12.0(3) . . . . ?
N2 C16 C17 C18 -168.90(18) . . . . ?
C16 C17 C18 C19 64.9(3) . . . . ?
C17 C18 C19 C20 173.3(2) . . . . ?
C18 C19 C20 C21 174.8(2) . . . . ?
C19 C20 C21 C22 -175.5(2) . . . . ?
C20 C21 C22 C23 -178.5(2) . . . . ?
C28 O5 C24 C25 -166.25(17) . . . . ?
O5 C24 C25 O6 171.50(17) . . . . ?
C24 C25 O6 C26 -175.42(19) . . . . ?
C25 O6 C26 O7 -2.4(3) . . . . ?
C25 O6 C26 C27 176.9(2) . . . . ?
C24 O5 C28 C37 171.72(18) . . . . ?
C24 O5 C28 C29 -10.2(3) . . . . ?
O5 C28 C29 C30 -178.43(19) . . . . ?
C37 C28 C29 C30 -0.4(3) . . . . ?
C28 C29 C30 C31 -0.6(3) . . . . ?
C29 C30 C31 C32 -179.0(2) . . . . ?
C29 C30 C31 C36 0.9(3) . . . . ?
C30 C31 C32 C33 179.3(2) . . . . ?
C36 C31 C32 C33 -0.7(3) . . . . ?
C31 C32 C33 C34 0.1(3) . . . . ?
C32 C33 C34 C35 0.2(3) . . . . ?
C33 C34 C35 C36 0.0(3) . . . . ?
C34 C35 C36 C31 -0.5(3) . . . . ?
C34 C35 C36 C37 -179.3(2) . . . . ?
C32 C31 C36 C35 0.9(3) . . . . ?
C30 C31 C36 C35 -179.09(19) . . . . ?
C32 C31 C36 C37 179.68(19) . . . . ?
C30 C31 C36 C37 -0.3(3) . . . . ?
O5 C28 C37 C36 179.18(18) . . . . ?
C29 C28 C37 C36 1.1(3) . . . . ?
O5 C28 C37 C38 5.7(3) . . . . ?
C29 C28 C37 C38 -172.4(2) . . . . ?
C35 C36 C37 C28 178.03(19) . . . . ?
C31 C36 C37 C28 -0.7(3) . . . . ?
C35 C36 C37 C38 -8.3(3) . . . . ?
C31 C36 C37 C38 172.97(18) . . . . ?
C28 C37 C38 N3 -57.6(3) . . . . ?
C36 C37 C38 N3 128.9(2) . . . . ?
C37 C38 N3 N4 -2.0(3) . . . . ?
C38 N3 N4 C39 -179.25(18) . . . . ?
N3 N4 C39 O8 -2.7(3) . . . . ?
N3 N4 C39 C40 175.72(17) . . . . ?
O8 C39 C40 C41 -23.3(3) . . . . ?
N4 C39 C40 C41 158.25(18) . . . . ?
C39 C40 C41 C42 -69.5(2) . . . . ?
C40 C41 C42 C43 179.27(19) . . . . ?
C41 C42 C43 C44 -166.1(2) . . . . ?
C42 C43 C44 C45 174.7(2) . . . . ?
C43 C44 C45 C46 -170.6(2) . . . . ?

_refine_diff_density_max         0.616
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.056



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_E-d7-S
_database_code_depnum_ccdc_archive 'CCDC 2431299'
loop_
_audit_author_name
_audit_author_address
'Isao Yoshikawa'
;Institute of Industrial Science, The University of Tokyo
Japan
;
_audit_update_record             
;
2025-03-14 deposited with the CCDC.	2025-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H30 N2 O4'
_chemical_formula_sum            'C23 H30 N2 O4'
_chemical_formula_weight         398.49

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   12.1158(7)
_cell_length_b                   5.2152(3)
_cell_length_c                   33.911(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.589(6)
_cell_angle_gamma                90
_cell_volume                     2138.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1757
_cell_measurement_theta_min      7.3270
_cell_measurement_theta_max      67.5300

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_shelx_estimated_absorpt_T_min   0.910
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_coefficient_mu    0.684
_exptl_absorpt_correction_T_min  0.829
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.90 (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            20657
_diffrn_reflns_av_unetI/netI     0.0800
_diffrn_reflns_av_R_equivalents  0.0785
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         3.655
_diffrn_reflns_theta_max         72.520
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4172
_reflns_number_gt                2365
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.90 (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.90 (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1128P)²+6.5590P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4172
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1809
_refine_ls_R_factor_gt           0.1288
_refine_ls_wR_factor_ref         0.3701
_refine_ls_wR_factor_gt          0.3390
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2611(3) 0.8342(8) 0.22683(13) 0.0686(12) Uani 1 1 d . . . . .
C1 C 0.2672(6) 1.0188(14) 0.1971(2) 0.080(2) Uani 1 1 d . . . . .
H1 H 0.340619 1.012681 0.185810 0.096 Uiso 1 1 calc R U . . .
H2 H 0.256353 1.192373 0.207968 0.096 Uiso 1 1 calc R U . . .
C2 C 0.1800(8) 0.962(2) 0.1663(2) 0.112(3) Uani 1 1 d . . . . .
H3 H 0.189467 0.778386 0.159706 0.134 Uiso 0.529(11) 1 calc R U P A 1
H4 H 0.109584 0.973193 0.179562 0.134 Uiso 0.529(11) 1 calc R U P A 1
H5 H 0.118395 0.865905 0.177345 0.134 Uiso 0.471(11) 1 calc R U P A 2
H6 H 0.150635 1.120646 0.153660 0.134 Uiso 0.471(11) 1 calc R U P A 2
O2 O 0.1616(7) 1.0828(16) 0.1315(3) 0.069(3) Uiso 0.529(11) 1 d . . P A 1
C3 C 0.198(2) 1.018(5) 0.0982(6) 0.100(6) Uiso 0.529(11) 1 d . . P A 1
O3 O 0.2458(10) 0.787(3) 0.0979(4) 0.094(4) Uiso 0.529(11) 1 d . . P A 1
C4 C 0.1880(13) 1.185(3) 0.0653(5) 0.093(5) Uiso 0.529(11) 1 d . . P A 1
H7 H 0.219986 1.103495 0.042593 0.139 Uiso 0.529(11) 1 calc R U P A 1
H8 H 0.109744 1.222850 0.058698 0.139 Uiso 0.529(11) 1 calc R U P A 1
H9 H 0.227571 1.345251 0.071701 0.139 Uiso 0.529(11) 1 calc R U P A 1
O4 O 0.2299(10) 0.824(2) 0.1420(3) 0.093(4) Uiso 0.471(11) 1 d . . P A 2
C5 C 0.2019(19) 0.897(5) 0.1029(6) 0.083(6) Uiso 0.471(11) 1 d . . P A 2
O5 O 0.2405(18) 0.681(5) 0.0766(7) 0.178(8) Uiso 0.471(11) 1 d . . P A 2
C6 C 0.1407(17) 1.055(3) 0.0916(5) 0.080(5) Uiso 0.471(11) 1 d . . P A 2
H10 H 0.138511 1.061085 0.062706 0.121 Uiso 0.471(11) 1 calc R U P A 2
H11 H 0.066805 1.015183 0.100135 0.121 Uiso 0.471(11) 1 calc R U P A 2
H12 H 0.164997 1.220924 0.102460 0.121 Uiso 0.471(11) 1 calc R U P A 2
C7 C 0.3273(4) 0.8458(11) 0.26105(19) 0.0584(15) Uani 1 1 d . . . . .
C8 C 0.4130(5) 1.0269(11) 0.2663(2) 0.0656(17) Uani 1 1 d . . . . .
H13 H 0.425700 1.148032 0.246192 0.079 Uiso 1 1 calc R U . . .
C9 C 0.4773(5) 1.0264(12) 0.3005(2) 0.0700(18) Uani 1 1 d . . . . .
H14 H 0.534359 1.150829 0.304029 0.084 Uiso 1 1 calc R U . . .
C10 C 0.4631(4) 0.8507(11) 0.3308(2) 0.0610(16) Uani 1 1 d . . . . .
C11 C 0.5321(5) 0.8555(13) 0.3661(2) 0.0701(18) Uani 1 1 d . . . . .
H15 H 0.588572 0.981387 0.369423 0.084 Uiso 1 1 calc R U . . .
C12 C 0.5184(5) 0.6838(14) 0.3949(2) 0.0722(19) Uani 1 1 d . . . . .
H16 H 0.565723 0.687642 0.418274 0.087 Uiso 1 1 calc R U . . .
C13 C 0.4346(5) 0.4988(13) 0.3905(2) 0.0674(17) Uani 1 1 d . . . . .
H17 H 0.425322 0.378789 0.411058 0.081 Uiso 1 1 calc R U . . .
C14 C 0.3665(4) 0.4889(11) 0.35705(19) 0.0596(15) Uani 1 1 d . . . . .
H18 H 0.310331 0.361801 0.354743 0.072 Uiso 1 1 calc R U . . .
C15 C 0.3776(4) 0.6636(10) 0.32572(19) 0.0557(14) Uani 1 1 d . . . . .
C16 C 0.3079(4) 0.6656(10) 0.28979(18) 0.0524(14) Uani 1 1 d . . . . .
C17 C 0.2150(4) 0.4929(10) 0.28069(18) 0.0537(14) Uani 1 1 d . . . . .
H19 H 0.174115 0.515679 0.256110 0.064 Uiso 1 1 calc R U . . .
N1 N 0.1839(3) 0.3114(8) 0.30345(14) 0.0525(12) Uani 1 1 d . . . . .
N2 N 0.0941(3) 0.1730(9) 0.28794(16) 0.0521(11) Uani 1 1 d . . . . .
H20 H 0.071(5) 0.201(13) 0.2609(19) 0.078 Uiso 1 1 d . U . . .
C18 C 0.0559(4) -0.0304(10) 0.30721(18) 0.0545(14) Uani 1 1 d . . . . .
O6 O -0.0219(3) -0.1563(8) 0.29151(13) 0.0660(12) Uani 1 1 d . . . . .
C19 C 0.1041(4) -0.0882(10) 0.34767(18) 0.0556(14) Uani 1 1 d . . . . .
H21 H 0.184856 -0.057502 0.348427 0.067 Uiso 1 1 calc R U . . .
H22 H 0.092551 -0.272185 0.353287 0.067 Uiso 1 1 calc R U . . .
C20 C 0.0557(5) 0.0689(14) 0.3797(2) 0.0744(19) Uani 1 1 d . . . . .
H23 H -0.025269 0.041711 0.378771 0.089 Uiso 1 1 calc R U . . .
H24 H 0.069178 0.252930 0.374744 0.089 Uiso 1 1 calc R U . . .
C21 C 0.1050(7) -0.001(3) 0.4208(3) 0.132(4) Uani 1 1 d . . . . .
H25 H 0.061171 0.093110 0.439818 0.159 Uiso 0.637(7) 1 calc R U P B 3
H26 H 0.089676 -0.185125 0.424544 0.159 Uiso 0.637(7) 1 calc R U P B 3
H27 H 0.186048 -0.025870 0.420941 0.159 Uiso 0.363(7) 1 calc R U P B 4
H28 H 0.070316 -0.156535 0.431143 0.159 Uiso 0.363(7) 1 calc R U P B 4
C22 C 0.2137(11) 0.036(3) 0.4329(4) 0.091(4) Uiso 0.637(7) 1 d . . P B 3
H29 H 0.224686 0.223036 0.436105 0.110 Uiso 0.637(7) 1 calc R U P B 3
H30 H 0.257975 -0.017853 0.410755 0.110 Uiso 0.637(7) 1 calc R U P B 3
C23 C 0.2677(11) -0.097(3) 0.4718(4) 0.101(4) Uiso 0.637(7) 1 d . . P B 3
H31 H 0.220307 -0.062796 0.493950 0.121 Uiso 0.637(7) 1 calc R U P B 3
H32 H 0.269682 -0.284376 0.467633 0.121 Uiso 0.637(7) 1 calc R U P B 3
C24 C 0.3814(13) -0.005(3) 0.4829(4) 0.112(5) Uiso 0.637(7) 1 d . . P B 3
H33 H 0.378642 0.178938 0.489744 0.135 Uiso 0.637(7) 1 calc R U P B 3
H34 H 0.427263 -0.023769 0.459944 0.135 Uiso 0.637(7) 1 calc R U P B 3
C25 C 0.4358(15) -0.153(4) 0.5180(5) 0.138(6) Uiso 0.637(7) 1 d . . P B 3
H35 H 0.510390 -0.086025 0.524147 0.208 Uiso 0.637(7) 1 calc R U P B 3
H36 H 0.391550 -0.132624 0.540983 0.208 Uiso 0.637(7) 1 calc R U P B 3
H37 H 0.440178 -0.335361 0.511178 0.208 Uiso 0.637(7) 1 calc R U P B 3
C26 C 0.0723(19) 0.267(4) 0.4469(6) 0.087(6) Uiso 0.363(7) 1 d . . P B 4
H38 H 0.101142 0.420417 0.433906 0.105 Uiso 0.363(7) 1 calc R U P B 4
H39 H -0.009176 0.282828 0.446696 0.105 Uiso 0.363(7) 1 calc R U P B 4
C27 C 0.119(2) 0.257(5) 0.4885(7) 0.104(8) Uiso 0.363(7) 1 d . . P B 4
H40 H 0.098719 0.090222 0.500060 0.125 Uiso 0.363(7) 1 calc R U P B 4
H41 H 0.083480 0.393451 0.503655 0.125 Uiso 0.363(7) 1 calc R U P B 4
C28 C 0.242(2) 0.289(5) 0.4933(7) 0.106(8) Uiso 0.363(7) 1 d . . P B 4
H42 H 0.277447 0.153143 0.478143 0.128 Uiso 0.363(7) 1 calc R U P B 4
H43 H 0.266174 0.266682 0.521520 0.128 Uiso 0.363(7) 1 calc R U P B 4
C29 C 0.284(3) 0.570(7) 0.4784(10) 0.151(12) Uiso 0.363(7) 1 d . . P B 4
H44 H 0.364806 0.579554 0.482215 0.226 Uiso 0.363(7) 1 calc R U P B 4
H45 H 0.261940 0.591678 0.450280 0.226 Uiso 0.363(7) 1 calc R U P B 4
H46 H 0.250660 0.705282 0.493682 0.226 Uiso 0.363(7) 1 calc R U P B 4


_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 C7 1.370(7) . ?
O1 C1 1.400(8) . ?
C1 C2 1.467(11) . ?
C1 H1 0.9900 . ?
C1 H2 0.9900 . ?
C2 O4 1.274(13) . ?
C2 O2 1.347(11) . ?
C2 H3 0.9900 . ?
C2 H4 0.9900 . ?
C2 H5 0.9900 . ?
C2 H6 0.9900 . ?
O2 C3 1.28(2) . ?
C3 O3 1.34(3) . ?
C3 C4 1.42(3) . ?
C4 H7 0.9800 . ?
C4 H8 0.9800 . ?
C4 H9 0.9800 . ?
O4 C5 1.40(2) . ?
C5 C6 1.15(3) . ?
C5 O5 1.53(3) . ?
C6 H10 0.9800 . ?
C6 H11 0.9800 . ?
C6 H12 0.9800 . ?
C7 C16 1.385(8) . ?
C7 C8 1.407(8) . ?
C8 C9 1.356(9) . ?
C8 H13 0.9500 . ?
C9 C10 1.395(9) . ?
C9 H14 0.9500 . ?
C10 C11 1.416(9) . ?
C10 C15 1.425(7) . ?
C11 C12 1.342(10) . ?
C11 H15 0.9500 . ?
C12 C13 1.402(9) . ?
C12 H16 0.9500 . ?
C13 C14 1.360(8) . ?
C13 H17 0.9500 . ?
C14 C15 1.412(8) . ?
C14 H18 0.9500 . ?
C15 C16 1.438(8) . ?
C16 C17 1.460(7) . ?
C17 N1 1.292(7) . ?
C17 H19 0.9500 . ?
N1 N2 1.382(5) . ?
N2 C18 1.343(7) . ?
N2 H20 0.95(7) . ?
C18 O6 1.241(6) . ?
C18 C19 1.488(8) . ?
C19 C20 1.509(8) . ?
C19 H21 0.9900 . ?
C19 H22 0.9900 . ?
C20 C21 1.524(11) . ?
C20 H23 0.9900 . ?
C20 H24 0.9900 . ?
C21 C22 1.367(14) . ?
C21 C26 1.71(2) . ?
C21 H25 0.9900 . ?
C21 H26 0.9900 . ?
C21 H27 0.9900 . ?
C21 H28 0.9900 . ?
C22 C23 1.593(17) . ?
C22 H29 0.9900 . ?
C22 H30 0.9900 . ?
C23 C24 1.483(19) . ?
C23 H31 0.9900 . ?
C23 H32 0.9900 . ?
C24 C25 1.53(2) . ?
C24 H33 0.9900 . ?
C24 H34 0.9900 . ?
C25 H35 0.9800 . ?
C25 H36 0.9800 . ?
C25 H37 0.9800 . ?
C26 C27 1.48(3) . ?
C26 H38 0.9900 . ?
C26 H39 0.9900 . ?
C27 C28 1.50(3) . ?
C27 H40 0.9900 . ?
C27 H41 0.9900 . ?
C28 C29 1.64(4) . ?
C28 H42 0.9900 . ?
C28 H43 0.9900 . ?
C29 H44 0.9800 . ?
C29 H45 0.9800 . ?
C29 H46 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 C1 121.7(5) . . ?
O1 C1 C2 107.7(7) . . ?
O1 C1 H1 110.2 . . ?
C2 C1 H1 110.2 . . ?
O1 C1 H2 110.2 . . ?
C2 C1 H2 110.2 . . ?
H1 C1 H2 108.5 . . ?
O4 C2 C1 102.9(9) . . ?
O2 C2 C1 126.9(10) . . ?
O2 C2 H3 105.6 . . ?
C1 C2 H3 105.6 . . ?
O2 C2 H4 105.6 . . ?
C1 C2 H4 105.6 . . ?
H3 C2 H4 106.1 . . ?
O4 C2 H5 111.2 . . ?
C1 C2 H5 111.2 . . ?
O4 C2 H6 111.2 . . ?
C1 C2 H6 111.2 . . ?
H5 C2 H6 109.1 . . ?
C3 O2 C2 127.0(14) . . ?
O2 C3 O3 115(2) . . ?
O2 C3 C4 121(2) . . ?
O3 C3 C4 124.2(18) . . ?
C3 C4 H7 109.5 . . ?
C3 C4 H8 109.5 . . ?
H7 C4 H8 109.5 . . ?
C3 C4 H9 109.5 . . ?
H7 C4 H9 109.5 . . ?
H8 C4 H9 109.5 . . ?
C2 O4 C5 111.4(15) . . ?
C6 C5 O4 128(2) . . ?
C6 C5 O5 123(2) . . ?
O4 C5 O5 107(2) . . ?
C5 C6 H10 109.5 . . ?
C5 C6 H11 109.5 . . ?
H10 C6 H11 109.5 . . ?
C5 C6 H12 109.5 . . ?
H10 C6 H12 109.5 . . ?
H11 C6 H12 109.5 . . ?
O1 C7 C16 116.7(5) . . ?
O1 C7 C8 121.7(6) . . ?
C16 C7 C8 121.5(6) . . ?
C9 C8 C7 119.2(6) . . ?
C9 C8 H13 120.4 . . ?
C7 C8 H13 120.4 . . ?
C8 C9 C10 122.7(6) . . ?
C8 C9 H14 118.7 . . ?
C10 C9 H14 118.7 . . ?
C9 C10 C11 121.1(6) . . ?
C9 C10 C15 118.9(6) . . ?
C11 C10 C15 120.0(6) . . ?
C12 C11 C10 120.6(6) . . ?
C12 C11 H15 119.7 . . ?
C10 C11 H15 119.7 . . ?
C11 C12 C13 120.2(6) . . ?
C11 C12 H16 119.9 . . ?
C13 C12 H16 119.9 . . ?
C14 C13 C12 120.8(7) . . ?
C14 C13 H17 119.6 . . ?
C12 C13 H17 119.6 . . ?
C13 C14 C15 121.4(6) . . ?
C13 C14 H18 119.3 . . ?
C15 C14 H18 119.3 . . ?
C14 C15 C10 116.9(5) . . ?
C14 C15 C16 124.3(5) . . ?
C10 C15 C16 118.8(5) . . ?
C7 C16 C15 119.0(5) . . ?
C7 C16 C17 115.6(5) . . ?
C15 C16 C17 125.4(5) . . ?
N1 C17 C16 125.1(5) . . ?
N1 C17 H19 117.4 . . ?
C16 C17 H19 117.4 . . ?
C17 N1 N2 114.0(5) . . ?
C18 N2 N1 121.0(5) . . ?
C18 N2 H20 120(4) . . ?
N1 N2 H20 117(4) . . ?
O6 C18 N2 119.0(5) . . ?
O6 C18 C19 122.2(5) . . ?
N2 C18 C19 118.7(5) . . ?
C18 C19 C20 114.0(5) . . ?
C18 C19 H21 108.8 . . ?
C20 C19 H21 108.8 . . ?
C18 C19 H22 108.8 . . ?
C20 C19 H22 108.8 . . ?
H21 C19 H22 107.6 . . ?
C19 C20 C21 112.4(6) . . ?
C19 C20 H23 109.1 . . ?
C21 C20 H23 109.1 . . ?
C19 C20 H24 109.1 . . ?
C21 C20 H24 109.1 . . ?
H23 C20 H24 107.8 . . ?
C22 C21 C20 123.8(10) . . ?
C20 C21 C26 100.9(11) . . ?
C22 C21 H25 106.4 . . ?
C20 C21 H25 106.4 . . ?
C22 C21 H26 106.4 . . ?
C20 C21 H26 106.4 . . ?
H25 C21 H26 106.5 . . ?
C20 C21 H27 111.6 . . ?
C26 C21 H27 111.6 . . ?
C20 C21 H28 111.6 . . ?
C26 C21 H28 111.6 . . ?
H27 C21 H28 109.4 . . ?
C21 C22 C23 121.7(12) . . ?
C21 C22 H29 106.9 . . ?
C23 C22 H29 106.9 . . ?
C21 C22 H30 106.9 . . ?
C23 C22 H30 106.9 . . ?
H29 C22 H30 106.7 . . ?
C24 C23 C22 113.5(12) . . ?
C24 C23 H31 108.9 . . ?
C22 C23 H31 108.9 . . ?
C24 C23 H32 108.9 . . ?
C22 C23 H32 108.9 . . ?
H31 C23 H32 107.7 . . ?
C23 C24 C25 112.6(14) . . ?
C23 C24 H33 109.1 . . ?
C25 C24 H33 109.1 . . ?
C23 C24 H34 109.1 . . ?
C25 C24 H34 109.1 . . ?
H33 C24 H34 107.8 . . ?
C24 C25 H35 109.5 . . ?
C24 C25 H36 109.5 . . ?
H35 C25 H36 109.5 . . ?
C24 C25 H37 109.5 . . ?
H35 C25 H37 109.5 . . ?
H36 C25 H37 109.5 . . ?
C27 C26 C21 112.2(17) . . ?
C27 C26 H38 109.2 . . ?
C21 C26 H38 109.2 . . ?
C27 C26 H39 109.2 . . ?
C21 C26 H39 109.2 . . ?
H38 C26 H39 107.9 . . ?
C26 C27 C28 114(2) . . ?
C26 C27 H40 108.6 . . ?
C28 C27 H40 108.6 . . ?
C26 C27 H41 108.6 . . ?
C28 C27 H41 108.6 . . ?
H40 C27 H41 107.6 . . ?
C27 C28 C29 113(2) . . ?
C27 C28 H42 109.0 . . ?
C29 C28 H42 109.0 . . ?
C27 C28 H43 109.0 . . ?
C29 C28 H43 109.0 . . ?
H42 C28 H43 107.8 . . ?
C28 C29 H44 109.5 . . ?
C28 C29 H45 109.5 . . ?
H44 C29 H45 109.5 . . ?
C28 C29 H46 109.5 . . ?
H44 C29 H46 109.5 . . ?
H45 C29 H46 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 O1 C1 C2 -175.5(6) . . . . ?
O1 C1 C2 O4 -93.8(9) . . . . ?
O1 C1 C2 O2 -175.6(8) . . . . ?
C1 C2 O2 C3 94.2(18) . . . . ?
C2 O2 C3 O3 10(3) . . . . ?
C2 O2 C3 C4 -169.1(15) . . . . ?
C1 C2 O4 C5 -136.3(12) . . . . ?
C2 O4 C5 C6 -2(3) . . . . ?
C2 O4 C5 O5 -165.3(14) . . . . ?
C1 O1 C7 C16 174.8(5) . . . . ?
C1 O1 C7 C8 -7.1(8) . . . . ?
O1 C7 C8 C9 -178.7(5) . . . . ?
C16 C7 C8 C9 -0.7(9) . . . . ?
C7 C8 C9 C10 0.9(9) . . . . ?
C8 C9 C10 C11 179.8(6) . . . . ?
C8 C9 C10 C15 0.0(9) . . . . ?
C9 C10 C11 C12 -179.3(6) . . . . ?
C15 C10 C11 C12 0.5(9) . . . . ?
C10 C11 C12 C13 -0.7(9) . . . . ?
C11 C12 C13 C14 0.4(9) . . . . ?
C12 C13 C14 C15 0.0(9) . . . . ?
C13 C14 C15 C10 -0.2(8) . . . . ?
C13 C14 C15 C16 -179.4(6) . . . . ?
C9 C10 C15 C14 179.7(5) . . . . ?
C11 C10 C15 C14 -0.1(8) . . . . ?
C9 C10 C15 C16 -1.0(8) . . . . ?
C11 C10 C15 C16 179.2(5) . . . . ?
O1 C7 C16 C15 177.8(5) . . . . ?
C8 C7 C16 C15 -0.3(8) . . . . ?
O1 C7 C16 C17 -3.0(7) . . . . ?
C8 C7 C16 C17 178.9(5) . . . . ?
C14 C15 C16 C7 -179.6(5) . . . . ?
C10 C15 C16 C7 1.1(8) . . . . ?
C14 C15 C16 C17 1.3(9) . . . . ?
C10 C15 C16 C17 -177.9(5) . . . . ?
C7 C16 C17 N1 179.6(5) . . . . ?
C15 C16 C17 N1 -1.3(9) . . . . ?
C16 C17 N1 N2 -179.4(5) . . . . ?
C17 N1 N2 C18 176.4(5) . . . . ?
N1 N2 C18 O6 -176.9(5) . . . . ?
N1 N2 C18 C19 6.5(8) . . . . ?
O6 C18 C19 C20 -94.5(7) . . . . ?
N2 C18 C19 C20 81.9(7) . . . . ?
C18 C19 C20 C21 178.5(6) . . . . ?
C19 C20 C21 C22 64.5(14) . . . . ?
C19 C20 C21 C26 160.6(9) . . . . ?
C20 C21 C22 C23 -165.5(11) . . . . ?
C21 C22 C23 C24 -172.0(13) . . . . ?
C22 C23 C24 C25 -174.5(13) . . . . ?
C20 C21 C26 C27 -176.0(16) . . . . ?
C21 C26 C27 C28 71(3) . . . . ?
C26 C27 C28 C29 63(3) . . . . ?

_refine_diff_density_max         0.545
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.075



_exptl_crystal_recrystallization_method 'From the Melt'
_exptl_crystal_preparation       photochromic
####################################################################### 
# 
# 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_Z-e7
_database_code_depnum_ccdc_archive 'CCDC 2431303'
loop_
_audit_author_name
_audit_author_address
'Isao Yoshikawa'
;Institute of Industrial Science, The University of Tokyo
Japan
;
_audit_update_record             
;
2025-03-14 deposited with the CCDC.	2025-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H30 N2 O4'
_chemical_formula_sum            'C23 H30 N2 O4'
_chemical_formula_weight         398.49

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   8.1133(2)
_cell_length_b                   13.2489(3)
_cell_length_c                   40.4914(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4352.5(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    16032
_cell_measurement_theta_min      3.9390
_cell_measurement_theta_max      71.2350

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_F_000             1712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.671
_shelx_estimated_absorpt_T_min   0.799
_shelx_estimated_absorpt_T_max   0.948
_exptl_absorpt_correction_T_min  0.63730
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            50190
_diffrn_reflns_av_unetI/netI     0.0641
_diffrn_reflns_av_R_equivalents  0.1623
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_theta_min         3.510
_diffrn_reflns_theta_max         71.497
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8344
_reflns_number_gt                7780
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_max     0.979
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'CrysAlisPro 1.171.41.107a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_refine_special_details          Twin
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2944 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         8344
_refine_ls_number_parameters     527
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1354
_refine_ls_R_factor_gt           0.1315
_refine_ls_wR_factor_ref         0.3548
_refine_ls_wR_factor_gt          0.3466
_refine_ls_goodness_of_fit_ref   1.631
_refine_ls_restrained_S_all      1.631
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1118(5) 0.3622(3) 0.30566(11) 0.0268(10) Uani 1 1 d . . . . .
C1 C 0.0310(7) 0.2865(5) 0.32390(15) 0.0255(13) Uani 1 1 d . . . . .
H1 H 0.075324 0.219403 0.317817 0.031 Uiso 1 1 calc R U . . .
H2 H -0.088417 0.287295 0.318882 0.031 Uiso 1 1 calc R U . . .
C2 C 0.0579(8) 0.3055(5) 0.36011(16) 0.0298(14) Uani 1 1 d . . . . .
O2 O 0.1267(6) 0.3781(4) 0.37201(11) 0.0341(11) Uani 1 1 d . . . . .
O3 O -0.0091(7) 0.2313(4) 0.37794(11) 0.0394(12) Uani 1 1 d . . . . .
C3 C -0.0094(15) 0.2470(8) 0.41262(19) 0.059(3) Uani 1 1 d . . . . .
H3 H -0.066969 0.310810 0.417975 0.071 Uiso 1 1 calc R U . . .
H4 H 0.105148 0.251641 0.420905 0.071 Uiso 1 1 calc R U . . .
C4 C -0.0956(18) 0.1603(8) 0.4285(2) 0.071(3) Uani 1 1 d . . . . .
H5 H -0.032130 0.098371 0.424777 0.106 Uiso 1 1 calc R U . . .
H6 H -0.205636 0.152827 0.418782 0.106 Uiso 1 1 calc R U . . .
H7 H -0.105705 0.172658 0.452234 0.106 Uiso 1 1 calc R U . . .
C5 C 0.0823(6) 0.3677(4) 0.27311(15) 0.0195(11) Uani 1 1 d . . . . .
C6 C -0.0206(7) 0.2973(4) 0.25579(15) 0.0230(12) Uani 1 1 d . . . . .
H8 H -0.077614 0.246100 0.267613 0.028 Uiso 1 1 calc R U . . .
C7 C -0.0361(8) 0.3037(4) 0.22293(16) 0.0262(13) Uani 1 1 d . . . . .
H9 H -0.100085 0.254107 0.211862 0.031 Uiso 1 1 calc R U . . .
C8 C 0.0390(7) 0.3818(4) 0.20368(15) 0.0234(12) Uani 1 1 d . . . . .
C9 C 0.0238(8) 0.3876(5) 0.16955(15) 0.0275(13) Uani 1 1 d . . . . .
H10 H -0.035431 0.336374 0.158186 0.033 Uiso 1 1 calc R U . . .
C10 C 0.0926(9) 0.4659(6) 0.15174(17) 0.0318(14) Uani 1 1 d . . . . .
H11 H 0.077455 0.470085 0.128512 0.038 Uiso 1 1 calc R U . . .
C11 C 0.1835(8) 0.5378(5) 0.16823(16) 0.0297(14) Uani 1 1 d . . . . .
H12 H 0.232053 0.591455 0.156110 0.036 Uiso 1 1 calc R U . . .
C12 C 0.2055(8) 0.5334(5) 0.20216(16) 0.0278(13) Uani 1 1 d . . . . .
H13 H 0.266640 0.584868 0.212975 0.033 Uiso 1 1 calc R U . . .
C13 C 0.1386(7) 0.4537(4) 0.22076(15) 0.0218(12) Uani 1 1 d . . . . .
C14 C 0.1585(7) 0.4467(4) 0.25561(15) 0.0205(12) Uani 1 1 d . . . . .
C15 C 0.2795(7) 0.5154(5) 0.27171(14) 0.0231(12) Uani 1 1 d . . . . .
H14 H 0.381104 0.519965 0.260138 0.028 Uiso 1 1 calc R U . . .
N1 N 0.2754(6) 0.5699(4) 0.29799(12) 0.0215(10) Uani 1 1 d . . . . .
N2 N 0.1389(6) 0.5687(4) 0.31767(12) 0.0218(10) Uani 1 1 d . . . . .
H15 H 0.055564 0.528550 0.313114 0.026 Uiso 1 1 calc R U . . .
C16 C 0.1337(8) 0.6307(4) 0.34446(14) 0.0210(11) Uani 1 1 d . . . . .
O4 O 0.2413(6) 0.6922(3) 0.35075(10) 0.0283(10) Uani 1 1 d . . . . .
C17 C -0.0215(8) 0.6197(5) 0.36470(15) 0.0285(13) Uani 1 1 d . . . . .
H16 H -0.048522 0.547147 0.366802 0.034 Uiso 1 1 calc R U . . .
H17 H -0.113606 0.652886 0.352898 0.034 Uiso 1 1 calc R U . . .
C18 C -0.0066(8) 0.6652(5) 0.39893(14) 0.0283(13) Uani 1 1 d . . . . .
H18 H -0.116722 0.664657 0.409456 0.034 Uiso 1 1 calc R U . . .
H19 H 0.027968 0.736542 0.396706 0.034 Uiso 1 1 calc R U . . .
C19 C 0.1143(9) 0.6115(6) 0.42160(17) 0.0337(14) Uani 1 1 d . . . . .
H20 H 0.081652 0.539779 0.423601 0.040 Uiso 1 1 calc R U . . .
H21 H 0.225484 0.613740 0.411561 0.040 Uiso 1 1 calc R U . . .
C20 C 0.1217(9) 0.6579(6) 0.45567(16) 0.0360(15) Uani 1 1 d . . . . .
H22 H 0.011135 0.653524 0.465899 0.043 Uiso 1 1 calc R U . . .
H23 H 0.149943 0.730284 0.453496 0.043 Uiso 1 1 calc R U . . .
C21 C 0.2476(11) 0.6074(7) 0.47880(18) 0.0465(19) Uani 1 1 d . . . . .
H24 H 0.219633 0.535123 0.481355 0.056 Uiso 1 1 calc R U . . .
H25 H 0.358861 0.611887 0.468861 0.056 Uiso 1 1 calc R U . . .
C22 C 0.2490(14) 0.6573(7) 0.5122(2) 0.054(2) Uani 1 1 d . . . . .
H26 H 0.135690 0.658078 0.521279 0.065 Uiso 1 1 calc R U . . .
H27 H 0.286132 0.728095 0.509843 0.065 Uiso 1 1 calc R U . . .
C23 C 0.3642(17) 0.6016(11) 0.5365(2) 0.077(3) Uani 1 1 d . . . . .
H28 H 0.478522 0.607942 0.528995 0.115 Uiso 1 1 calc R U . . .
H29 H 0.333772 0.530018 0.537406 0.115 Uiso 1 1 calc R U . . .
H30 H 0.353333 0.631339 0.558562 0.115 Uiso 1 1 calc R U . . .
O5 O 0.3917(5) 0.2385(3) 0.19298(10) 0.0235(9) Uani 1 1 d . . . . .
C24 C 0.4743(8) 0.3171(4) 0.17535(14) 0.0239(12) Uani 1 1 d . . . . .
H31 H 0.592903 0.317586 0.181105 0.029 Uiso 1 1 calc R U . . .
H32 H 0.426769 0.383459 0.181316 0.029 Uiso 1 1 calc R U . . .
C25 C 0.4533(8) 0.2984(5) 0.13931(16) 0.0273(13) Uani 1 1 d . . . . .
O6 O 0.3820(6) 0.2310(4) 0.12616(11) 0.0341(11) Uani 1 1 d . . . . .
O7 O 0.5447(7) 0.3695(4) 0.12338(11) 0.0370(12) Uani 1 1 d . . . . .
C26 C 0.5637(12) 0.3572(7) 0.08807(18) 0.050(2) Uani 1 1 d . . . . .
H33 H 0.460880 0.376695 0.076530 0.060 Uiso 1 1 calc R U . . .
H34 H 0.588824 0.285979 0.082679 0.060 Uiso 1 1 calc R U . . .
C27 C 0.7033(13) 0.4245(7) 0.0776(2) 0.053(2) Uani 1 1 d . . . . .
H35 H 0.802624 0.407015 0.090114 0.080 Uiso 1 1 calc R U . . .
H36 H 0.674081 0.495038 0.081800 0.080 Uiso 1 1 calc R U . . .
H37 H 0.724426 0.415141 0.053928 0.080 Uiso 1 1 calc R U . . .
C28 C 0.4182(7) 0.2319(4) 0.22601(15) 0.0204(12) Uani 1 1 d . . . . .
C29 C 0.5159(8) 0.3039(5) 0.24348(15) 0.0256(13) Uani 1 1 d . . . . .
H38 H 0.567931 0.357015 0.231663 0.031 Uiso 1 1 calc R U . . .
C30 C 0.5355(7) 0.2977(4) 0.27654(15) 0.0243(12) Uani 1 1 d . . . . .
H39 H 0.600919 0.346719 0.287558 0.029 Uiso 1 1 calc R U . . .
C31 C 0.4600(7) 0.2191(4) 0.29525(15) 0.0236(12) Uani 1 1 d . . . . .
C32 C 0.4786(8) 0.2129(5) 0.32978(17) 0.0297(13) Uani 1 1 d . . . . .
H40 H 0.542310 0.262053 0.341129 0.036 Uiso 1 1 calc R U . . .
C33 C 0.4043(9) 0.1354(5) 0.34725(16) 0.0308(14) Uani 1 1 d . . . . .
H41 H 0.414096 0.132686 0.370612 0.037 Uiso 1 1 calc R U . . .
C34 C 0.3136(8) 0.0600(5) 0.33021(16) 0.0274(13) Uani 1 1 d . . . . .
H42 H 0.266099 0.005629 0.342203 0.033 Uiso 1 1 calc R U . . .
C35 C 0.2940(7) 0.0647(5) 0.29706(17) 0.0265(13) Uani 1 1 d . . . . .
H43 H 0.232234 0.013490 0.286281 0.032 Uiso 1 1 calc R U . . .
C36 C 0.3639(7) 0.1450(4) 0.27759(14) 0.0217(12) Uani 1 1 d . . . . .
C37 C 0.3423(7) 0.1532(4) 0.24276(14) 0.0210(12) Uani 1 1 d . . . . .
C38 C 0.2248(7) 0.0822(5) 0.22693(14) 0.0242(12) Uani 1 1 d . . . . .
H44 H 0.126223 0.073297 0.239244 0.029 Uiso 1 1 calc R U . . .
N3 N 0.2278(6) 0.0310(4) 0.20059(12) 0.0215(10) Uani 1 1 d . . . . .
N4 N 0.3634(6) 0.0315(4) 0.18069(13) 0.0232(11) Uani 1 1 d . . . . .
H45 H 0.447956 0.070486 0.185432 0.028 Uiso 1 1 calc R U . . .
C39 C 0.3671(7) -0.0292(5) 0.15322(15) 0.0224(12) Uani 1 1 d . . . . .
O8 O 0.2620(5) -0.0946(3) 0.14846(11) 0.0266(10) Uani 1 1 d . . . . .
C40 C 0.5128(7) -0.0144(5) 0.13154(16) 0.0264(13) Uani 1 1 d . . . . .
H46 H 0.612314 -0.038395 0.143302 0.032 Uiso 1 1 calc R U . . .
H47 H 0.526760 0.058717 0.127333 0.032 Uiso 1 1 calc R U . . .
C41 C 0.5005(8) -0.0695(5) 0.09834(15) 0.0287(13) Uani 1 1 d . . . . .
H48 H 0.608295 -0.064801 0.086996 0.034 Uiso 1 1 calc R U . . .
H49 H 0.478237 -0.141768 0.102598 0.034 Uiso 1 1 calc R U . . .
C42 C 0.3669(9) -0.0286(6) 0.07519(18) 0.0353(15) Uani 1 1 d . . . . .
H50 H 0.259065 -0.031556 0.086611 0.042 Uiso 1 1 calc R U . . .
H51 H 0.390678 0.043065 0.070205 0.042 Uiso 1 1 calc R U . . .
C43 C 0.3551(11) -0.0872(7) 0.04291(17) 0.0464(19) Uani 1 1 d . . . . .
H52 H 0.354838 -0.160187 0.048080 0.056 Uiso 1 1 calc R U . . .
H53 H 0.455214 -0.073075 0.029705 0.056 Uiso 1 1 calc R U . . .
C44 C 0.2036(12) -0.0636(8) 0.0216(2) 0.052(2) Uani 1 1 d . . . . .
H54 H 0.103274 -0.073556 0.035166 0.063 Uiso 1 1 calc R U . . .
H55 H 0.207502 0.008347 0.015071 0.063 Uiso 1 1 calc R U . . .
C45 C 0.1901(14) -0.1281(9) -0.0093(2) 0.063(3) Uani 1 1 d . . . . .
H56 H 0.278211 -0.107983 -0.024906 0.076 Uiso 1 1 calc R U . . .
H57 H 0.209036 -0.199568 -0.003265 0.076 Uiso 1 1 calc R U . . .
C46 C 0.0276(15) -0.1198(11) -0.0264(3) 0.077(3) Uani 1 1 d . . . . .
H58 H 0.012091 -0.050488 -0.034283 0.115 Uiso 1 1 calc R U . . .
H59 H -0.060875 -0.137100 -0.010934 0.115 Uiso 1 1 calc R U . . .
H60 H 0.024913 -0.166297 -0.045217 0.115 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.342(7) . ?
O1 C1 1.407(7) . ?
C1 C2 1.504(9) . ?
C1 H1 0.9900 . ?
C1 H2 0.9900 . ?
C2 O2 1.212(8) . ?
C2 O3 1.335(8) . ?
O3 C3 1.420(9) . ?
C3 C4 1.490(13) . ?
C3 H3 0.9900 . ?
C3 H4 0.9900 . ?
C4 H5 0.9800 . ?
C4 H6 0.9800 . ?
C4 H7 0.9800 . ?
C5 C14 1.407(8) . ?
C5 C6 1.435(8) . ?
C6 C7 1.339(9) . ?
C6 H8 0.9500 . ?
C7 C8 1.432(8) . ?
C7 H9 0.9500 . ?
C8 C9 1.390(9) . ?
C8 C13 1.428(8) . ?
C9 C10 1.382(9) . ?
C9 H10 0.9500 . ?
C10 C11 1.377(10) . ?
C10 H11 0.9500 . ?
C11 C12 1.387(9) . ?
C11 H12 0.9500 . ?
C12 C13 1.406(8) . ?
C12 H13 0.9500 . ?
C13 C14 1.423(9) . ?
C14 C15 1.489(8) . ?
C15 N1 1.286(8) . ?
C15 H14 0.9500 . ?
N1 N2 1.364(7) . ?
N2 C16 1.361(7) . ?
N2 H15 0.8800 . ?
C16 O4 1.221(7) . ?
C16 C17 1.509(9) . ?
C17 C18 1.516(8) . ?
C17 H16 0.9900 . ?
C17 H17 0.9900 . ?
C18 C19 1.520(9) . ?
C18 H18 0.9900 . ?
C18 H19 0.9900 . ?
C19 C20 1.512(9) . ?
C19 H20 0.9900 . ?
C19 H21 0.9900 . ?
C20 C21 1.538(10) . ?
C20 H22 0.9900 . ?
C20 H23 0.9900 . ?
C21 C22 1.506(11) . ?
C21 H24 0.9900 . ?
C21 H25 0.9900 . ?
C22 C23 1.545(14) . ?
C22 H26 0.9900 . ?
C22 H27 0.9900 . ?
C23 H28 0.9800 . ?
C23 H29 0.9800 . ?
C23 H30 0.9800 . ?
O5 C28 1.357(7) . ?
O5 C24 1.430(7) . ?
C24 C25 1.490(9) . ?
C24 H31 0.9900 . ?
C24 H32 0.9900 . ?
C25 O6 1.189(8) . ?
C25 O7 1.362(8) . ?
O7 C26 1.448(9) . ?
C26 C27 1.503(12) . ?
C26 H33 0.9900 . ?
C26 H34 0.9900 . ?
C27 H35 0.9800 . ?
C27 H36 0.9800 . ?
C27 H37 0.9800 . ?
C28 C37 1.388(8) . ?
C28 C29 1.428(8) . ?
C29 C30 1.351(9) . ?
C29 H38 0.9500 . ?
C30 C31 1.426(8) . ?
C30 H39 0.9500 . ?
C31 C32 1.409(9) . ?
C31 C36 1.443(8) . ?
C32 C33 1.385(9) . ?
C32 H40 0.9500 . ?
C33 C34 1.420(9) . ?
C33 H41 0.9500 . ?
C34 C35 1.353(9) . ?
C34 H42 0.9500 . ?
C35 C36 1.440(8) . ?
C35 H43 0.9500 . ?
C36 C37 1.425(8) . ?
C37 C38 1.485(8) . ?
C38 N3 1.264(8) . ?
C38 H44 0.9500 . ?
N3 N4 1.364(7) . ?
N4 C39 1.373(8) . ?
N4 H45 0.8800 . ?
C39 O8 1.231(7) . ?
C39 C40 1.485(8) . ?
C40 C41 1.533(9) . ?
C40 H46 0.9900 . ?
C40 H47 0.9900 . ?
C41 C42 1.532(9) . ?
C41 H48 0.9900 . ?
C41 H49 0.9900 . ?
C42 C43 1.523(10) . ?
C42 H50 0.9900 . ?
C42 H51 0.9900 . ?
C43 C44 1.533(12) . ?
C43 H52 0.9900 . ?
C43 H53 0.9900 . ?
C44 C45 1.521(13) . ?
C44 H54 0.9900 . ?
C44 H55 0.9900 . ?
C45 C46 1.493(15) . ?
C45 H56 0.9900 . ?
C45 H57 0.9900 . ?
C46 H58 0.9800 . ?
C46 H59 0.9800 . ?
C46 H60 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C1 118.1(5) . . ?
O1 C1 C2 109.0(5) . . ?
O1 C1 H1 109.9 . . ?
C2 C1 H1 109.9 . . ?
O1 C1 H2 109.9 . . ?
C2 C1 H2 109.9 . . ?
H1 C1 H2 108.3 . . ?
O2 C2 O3 123.8(6) . . ?
O2 C2 C1 126.0(6) . . ?
O3 C2 C1 110.2(5) . . ?
C2 O3 C3 115.3(6) . . ?
O3 C3 C4 108.3(8) . . ?
O3 C3 H3 110.0 . . ?
C4 C3 H3 110.0 . . ?
O3 C3 H4 110.0 . . ?
C4 C3 H4 110.0 . . ?
H3 C3 H4 108.4 . . ?
C3 C4 H5 109.5 . . ?
C3 C4 H6 109.5 . . ?
H5 C4 H6 109.5 . . ?
C3 C4 H7 109.5 . . ?
H5 C4 H7 109.5 . . ?
H6 C4 H7 109.5 . . ?
O1 C5 C14 117.2(5) . . ?
O1 C5 C6 123.3(5) . . ?
C14 C5 C6 119.5(5) . . ?
C7 C6 C5 119.9(5) . . ?
C7 C6 H8 120.0 . . ?
C5 C6 H8 120.0 . . ?
C6 C7 C8 123.2(5) . . ?
C6 C7 H9 118.4 . . ?
C8 C7 H9 118.4 . . ?
C9 C8 C13 119.7(6) . . ?
C9 C8 C7 122.9(6) . . ?
C13 C8 C7 117.3(5) . . ?
C10 C9 C8 121.6(6) . . ?
C10 C9 H10 119.2 . . ?
C8 C9 H10 119.2 . . ?
C11 C10 C9 118.8(6) . . ?
C11 C10 H11 120.6 . . ?
C9 C10 H11 120.6 . . ?
C10 C11 C12 121.4(6) . . ?
C10 C11 H12 119.3 . . ?
C12 C11 H12 119.3 . . ?
C11 C12 C13 120.8(6) . . ?
C11 C12 H13 119.6 . . ?
C13 C12 H13 119.6 . . ?
C12 C13 C14 122.4(5) . . ?
C12 C13 C8 117.4(6) . . ?
C14 C13 C8 120.1(5) . . ?
C5 C14 C13 119.9(5) . . ?
C5 C14 C15 121.6(5) . . ?
C13 C14 C15 118.0(5) . . ?
N1 C15 C14 133.5(5) . . ?
N1 C15 H14 113.3 . . ?
C14 C15 H14 113.3 . . ?
C15 N1 N2 119.9(5) . . ?
C16 N2 N1 118.9(5) . . ?
C16 N2 H15 120.5 . . ?
N1 N2 H15 120.5 . . ?
O4 C16 N2 123.1(6) . . ?
O4 C16 C17 123.2(5) . . ?
N2 C16 C17 113.6(5) . . ?
C16 C17 C18 113.1(5) . . ?
C16 C17 H16 109.0 . . ?
C18 C17 H16 109.0 . . ?
C16 C17 H17 109.0 . . ?
C18 C17 H17 109.0 . . ?
H16 C17 H17 107.8 . . ?
C17 C18 C19 114.7(6) . . ?
C17 C18 H18 108.6 . . ?
C19 C18 H18 108.6 . . ?
C17 C18 H19 108.6 . . ?
C19 C18 H19 108.6 . . ?
H18 C18 H19 107.6 . . ?
C20 C19 C18 112.8(6) . . ?
C20 C19 H20 109.0 . . ?
C18 C19 H20 109.0 . . ?
C20 C19 H21 109.0 . . ?
C18 C19 H21 109.0 . . ?
H20 C19 H21 107.8 . . ?
C19 C20 C21 113.9(6) . . ?
C19 C20 H22 108.8 . . ?
C21 C20 H22 108.8 . . ?
C19 C20 H23 108.8 . . ?
C21 C20 H23 108.8 . . ?
H22 C20 H23 107.7 . . ?
C22 C21 C20 111.2(7) . . ?
C22 C21 H24 109.4 . . ?
C20 C21 H24 109.4 . . ?
C22 C21 H25 109.4 . . ?
C20 C21 H25 109.4 . . ?
H24 C21 H25 108.0 . . ?
C21 C22 C23 111.6(9) . . ?
C21 C22 H26 109.3 . . ?
C23 C22 H26 109.3 . . ?
C21 C22 H27 109.3 . . ?
C23 C22 H27 109.3 . . ?
H26 C22 H27 108.0 . . ?
C22 C23 H28 109.5 . . ?
C22 C23 H29 109.5 . . ?
H28 C23 H29 109.5 . . ?
C22 C23 H30 109.5 . . ?
H28 C23 H30 109.5 . . ?
H29 C23 H30 109.5 . . ?
C28 O5 C24 117.7(4) . . ?
O5 C24 C25 108.3(5) . . ?
O5 C24 H31 110.0 . . ?
C25 C24 H31 110.0 . . ?
O5 C24 H32 110.0 . . ?
C25 C24 H32 110.0 . . ?
H31 C24 H32 108.4 . . ?
O6 C25 O7 124.9(6) . . ?
O6 C25 C24 128.2(6) . . ?
O7 C25 C24 106.6(5) . . ?
C25 O7 C26 116.6(6) . . ?
O7 C26 C27 107.0(7) . . ?
O7 C26 H33 110.3 . . ?
C27 C26 H33 110.3 . . ?
O7 C26 H34 110.3 . . ?
C27 C26 H34 110.3 . . ?
H33 C26 H34 108.6 . . ?
C26 C27 H35 109.5 . . ?
C26 C27 H36 109.5 . . ?
H35 C27 H36 109.5 . . ?
C26 C27 H37 109.5 . . ?
H35 C27 H37 109.5 . . ?
H36 C27 H37 109.5 . . ?
O5 C28 C37 117.3(5) . . ?
O5 C28 C29 122.2(5) . . ?
C37 C28 C29 120.4(5) . . ?
C30 C29 C28 121.1(5) . . ?
C30 C29 H38 119.5 . . ?
C28 C29 H38 119.5 . . ?
C29 C30 C31 121.4(5) . . ?
C29 C30 H39 119.3 . . ?
C31 C30 H39 119.3 . . ?
C32 C31 C30 121.6(5) . . ?
C32 C31 C36 120.7(5) . . ?
C30 C31 C36 117.7(5) . . ?
C33 C32 C31 120.2(6) . . ?
C33 C32 H40 119.9 . . ?
C31 C32 H40 119.9 . . ?
C32 C33 C34 119.9(6) . . ?
C32 C33 H41 120.0 . . ?
C34 C33 H41 120.0 . . ?
C35 C34 C33 120.7(6) . . ?
C35 C34 H42 119.7 . . ?
C33 C34 H42 119.7 . . ?
C34 C35 C36 122.1(6) . . ?
C34 C35 H43 119.0 . . ?
C36 C35 H43 119.0 . . ?
C37 C36 C35 123.3(5) . . ?
C37 C36 C31 120.3(5) . . ?
C35 C36 C31 116.4(5) . . ?
C28 C37 C36 119.1(5) . . ?
C28 C37 C38 123.4(5) . . ?
C36 C37 C38 117.2(5) . . ?
N3 C38 C37 133.8(5) . . ?
N3 C38 H44 113.1 . . ?
C37 C38 H44 113.1 . . ?
C38 N3 N4 120.7(5) . . ?
N3 N4 C39 119.6(5) . . ?
N3 N4 H45 120.2 . . ?
C39 N4 H45 120.2 . . ?
O8 C39 N4 121.6(5) . . ?
O8 C39 C40 123.5(6) . . ?
N4 C39 C40 114.8(5) . . ?
C39 C40 C41 113.8(5) . . ?
C39 C40 H46 108.8 . . ?
C41 C40 H46 108.8 . . ?
C39 C40 H47 108.8 . . ?
C41 C40 H47 108.8 . . ?
H46 C40 H47 107.7 . . ?
C42 C41 C40 114.5(5) . . ?
C42 C41 H48 108.6 . . ?
C40 C41 H48 108.6 . . ?
C42 C41 H49 108.6 . . ?
C40 C41 H49 108.6 . . ?
H48 C41 H49 107.6 . . ?
C43 C42 C41 112.9(6) . . ?
C43 C42 H50 109.0 . . ?
C41 C42 H50 109.0 . . ?
C43 C42 H51 109.0 . . ?
C41 C42 H51 109.0 . . ?
H50 C42 H51 107.8 . . ?
C42 C43 C44 115.4(7) . . ?
C42 C43 H52 108.4 . . ?
C44 C43 H52 108.4 . . ?
C42 C43 H53 108.4 . . ?
C44 C43 H53 108.4 . . ?
H52 C43 H53 107.5 . . ?
C45 C44 C43 114.0(8) . . ?
C45 C44 H54 108.8 . . ?
C43 C44 H54 108.8 . . ?
C45 C44 H55 108.8 . . ?
C43 C44 H55 108.8 . . ?
H54 C44 H55 107.7 . . ?
C46 C45 C44 113.8(10) . . ?
C46 C45 H56 108.8 . . ?
C44 C45 H56 108.8 . . ?
C46 C45 H57 108.8 . . ?
C44 C45 H57 108.8 . . ?
H56 C45 H57 107.7 . . ?
C45 C46 H58 109.5 . . ?
C45 C46 H59 109.5 . . ?
H58 C46 H59 109.5 . . ?
C45 C46 H60 109.5 . . ?
H58 C46 H60 109.5 . . ?
H59 C46 H60 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 O1 C1 C2 -170.1(5) . . . . ?
O1 C1 C2 O2 5.2(9) . . . . ?
O1 C1 C2 O3 -176.3(5) . . . . ?
O2 C2 O3 C3 5.9(11) . . . . ?
C1 C2 O3 C3 -172.6(7) . . . . ?
C2 O3 C3 C4 177.1(9) . . . . ?
C1 O1 C5 C14 177.2(5) . . . . ?
C1 O1 C5 C6 -3.3(8) . . . . ?
O1 C5 C6 C7 -175.8(5) . . . . ?
C14 C5 C6 C7 3.7(8) . . . . ?
C5 C6 C7 C8 -3.3(9) . . . . ?
C6 C7 C8 C9 179.3(6) . . . . ?
C6 C7 C8 C13 1.9(8) . . . . ?
C13 C8 C9 C10 -5.0(9) . . . . ?
C7 C8 C9 C10 177.6(6) . . . . ?
C8 C9 C10 C11 2.4(10) . . . . ?
C9 C10 C11 C12 -0.6(10) . . . . ?
C10 C11 C12 C13 1.5(10) . . . . ?
C11 C12 C13 C14 -180.0(6) . . . . ?
C11 C12 C13 C8 -3.9(8) . . . . ?
C9 C8 C13 C12 5.6(8) . . . . ?
C7 C8 C13 C12 -176.8(5) . . . . ?
C9 C8 C13 C14 -178.3(5) . . . . ?
C7 C8 C13 C14 -0.7(8) . . . . ?
O1 C5 C14 C13 176.9(5) . . . . ?
C6 C5 C14 C13 -2.6(8) . . . . ?
O1 C5 C14 C15 5.8(8) . . . . ?
C6 C5 C14 C15 -173.7(5) . . . . ?
C12 C13 C14 C5 177.1(5) . . . . ?
C8 C13 C14 C5 1.1(8) . . . . ?
C12 C13 C14 C15 -11.4(8) . . . . ?
C8 C13 C14 C15 172.6(5) . . . . ?
C5 C14 C15 N1 -53.1(9) . . . . ?
C13 C14 C15 N1 135.6(7) . . . . ?
C14 C15 N1 N2 1.9(10) . . . . ?
C15 N1 N2 C16 -176.8(5) . . . . ?
N1 N2 C16 O4 4.6(8) . . . . ?
N1 N2 C16 C17 -178.2(5) . . . . ?
O4 C16 C17 C18 -19.2(8) . . . . ?
N2 C16 C17 C18 163.6(5) . . . . ?
C16 C17 C18 C19 -66.8(7) . . . . ?
C17 C18 C19 C20 -178.6(6) . . . . ?
C18 C19 C20 C21 -178.0(7) . . . . ?
C19 C20 C21 C22 179.9(7) . . . . ?
C20 C21 C22 C23 175.2(9) . . . . ?
C28 O5 C24 C25 169.4(5) . . . . ?
O5 C24 C25 O6 -0.1(9) . . . . ?
O5 C24 C25 O7 -175.0(5) . . . . ?
O6 C25 O7 C26 -4.2(10) . . . . ?
C24 C25 O7 C26 170.9(6) . . . . ?
C25 O7 C26 C27 -164.4(7) . . . . ?
C24 O5 C28 C37 -177.7(5) . . . . ?
C24 O5 C28 C29 4.0(7) . . . . ?
O5 C28 C29 C30 177.6(5) . . . . ?
C37 C28 C29 C30 -0.6(9) . . . . ?
C28 C29 C30 C31 0.2(9) . . . . ?
C29 C30 C31 C32 -179.3(6) . . . . ?
C29 C30 C31 C36 1.1(8) . . . . ?
C30 C31 C32 C33 -179.7(6) . . . . ?
C36 C31 C32 C33 -0.1(9) . . . . ?
C31 C32 C33 C34 2.1(10) . . . . ?
C32 C33 C34 C35 -2.2(10) . . . . ?
C33 C34 C35 C36 0.3(9) . . . . ?
C34 C35 C36 C37 -178.6(6) . . . . ?
C34 C35 C36 C31 1.6(8) . . . . ?
C32 C31 C36 C37 178.5(5) . . . . ?
C30 C31 C36 C37 -1.9(8) . . . . ?
C32 C31 C36 C35 -1.7(8) . . . . ?
C30 C31 C36 C35 177.9(5) . . . . ?
O5 C28 C37 C36 -178.6(5) . . . . ?
C29 C28 C37 C36 -0.3(8) . . . . ?
O5 C28 C37 C38 -5.1(8) . . . . ?
C29 C28 C37 C38 173.2(5) . . . . ?
C35 C36 C37 C28 -178.3(5) . . . . ?
C31 C36 C37 C28 1.5(8) . . . . ?
C35 C36 C37 C38 7.8(8) . . . . ?
C31 C36 C37 C38 -172.3(5) . . . . ?
C28 C37 C38 N3 48.7(10) . . . . ?
C36 C37 C38 N3 -137.7(7) . . . . ?
C37 C38 N3 N4 2.9(10) . . . . ?
C38 N3 N4 C39 176.3(5) . . . . ?
N3 N4 C39 O8 -10.4(8) . . . . ?
N3 N4 C39 C40 173.8(5) . . . . ?
O8 C39 C40 C41 14.0(8) . . . . ?
N4 C39 C40 C41 -170.3(5) . . . . ?
C39 C40 C41 C42 67.2(7) . . . . ?
C40 C41 C42 C43 -178.3(6) . . . . ?
C41 C42 C43 C44 168.8(7) . . . . ?
C42 C43 C44 C45 -176.3(8) . . . . ?
C43 C44 C45 C46 168.6(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H2 O8 0.99 2.49 3.064(7) 116.9 4 yes
N2 H15 O1 0.88 2.27 2.788(7) 117.4 . yes
N2 H15 N3 0.88 2.36 3.106(7) 142.0 4 yes
C17 H17 O6 0.99 2.56 3.296(8) 131.5 4 yes
C24 H31 O4 0.99 2.50 3.030(7) 113.4 4_645 yes
N4 H45 N1 0.88 2.34 3.097(7) 143.9 4_645 yes
N4 H45 O5 0.88 2.29 2.796(7) 116.4 . yes
C40 H46 O2 0.99 2.47 3.257(8) 136.3 4_645 yes
C40 H47 O6 0.99 2.57 3.427(8) 145.1 . yes

_refine_diff_density_max         0.842
_refine_diff_density_min         -0.711
_refine_diff_density_rms         0.148



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_Z-b7
_database_code_depnum_ccdc_archive 'CCDC 2431302'
loop_
_audit_author_name
_audit_author_address
'Isao Yoshikawa'
;Institute of Industrial Science, The University of Tokyo
Japan
;
_audit_update_record             
;
2025-03-14 deposited with the CCDC.	2025-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H34 N2 O2'
_chemical_formula_sum            'C24 H34 N2 O2'
_chemical_formula_weight         382.53

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.1719(2)
_cell_length_b                   18.6119(4)
_cell_length_c                   28.8584(9)
_cell_angle_alpha                95.236(2)
_cell_angle_beta                 90.111(2)
_cell_angle_gamma                96.1650(18)
_cell_volume                     4345.3(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    15231
_cell_measurement_theta_min      2.7020
_cell_measurement_theta_max      72.4600

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_F_000             1664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.020
_shelx_estimated_absorpt_T_min   0.777
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_coefficient_mu    0.580
_exptl_absorpt_correction_T_min  0.366
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            46790
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.398
_diffrn_reflns_theta_max         73.028
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             16558
_reflns_number_gt                14275
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'CrysAlisPro 1.171.41.107a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_refine_special_details          'Refined as a 2-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         16558
_refine_ls_number_parameters     1034
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1175
_refine_ls_R_factor_gt           0.1095
_refine_ls_wR_factor_ref         0.3673
_refine_ls_wR_factor_gt          0.3539
_refine_ls_goodness_of_fit_ref   1.616
_refine_ls_restrained_S_all      1.616
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.9033(3) 0.54512(14) 0.04507(9) 0.0287(6) Uani 1 1 d . . . . .
C1 C 0.8360(4) 0.5878(2) 0.01209(14) 0.0277(7) Uani 1 1 d . . . . .
H1 H 0.717041 0.589990 0.017675 0.033 Uiso 1 1 calc R U . . .
H2 H 0.849586 0.565672 -0.019999 0.033 Uiso 1 1 calc R U . . .
C2 C 0.9268(4) 0.6631(2) 0.01814(14) 0.0287(8) Uani 1 1 d . . . . .
H3 H 1.043890 0.660520 0.010132 0.034 Uiso 1 1 calc R U . . .
H4 H 0.922151 0.682510 0.051165 0.034 Uiso 1 1 calc R U . . .
C3 C 0.8547(5) 0.7141(2) -0.01206(16) 0.0353(9) Uani 1 1 d . . . . .
H5 H 0.735899 0.714172 -0.005348 0.042 Uiso 1 1 calc R U . . .
H6 H 0.865081 0.695950 -0.045128 0.042 Uiso 1 1 calc R U . . .
C4 C 0.9377(6) 0.7919(2) -0.0046(2) 0.0467(11) Uani 1 1 d . . . . .
H7 H 0.931537 0.809485 0.028668 0.056 Uiso 1 1 calc R U . . .
H8 H 1.055464 0.792303 -0.012739 0.056 Uiso 1 1 calc R U . . .
C5 C 0.8599(7) 0.8428(3) -0.0334(3) 0.0618(15) Uani 1 1 d . . . . .
H9 H 0.879552 0.829808 -0.066473 0.093 Uiso 1 1 calc R U . . .
H10 H 0.908266 0.892693 -0.024692 0.093 Uiso 1 1 calc R U . . .
H11 H 0.741132 0.839033 -0.027880 0.093 Uiso 1 1 calc R U . . .
C6 C 0.8253(4) 0.4787(2) 0.05064(13) 0.0267(7) Uani 1 1 d . . . . .
C7 C 0.6916(4) 0.4459(2) 0.02166(14) 0.0290(8) Uani 1 1 d . . . . .
H12 H 0.649268 0.471931 -0.001680 0.035 Uiso 1 1 calc R U . . .
C8 C 0.6248(4) 0.3773(2) 0.02746(13) 0.0291(8) Uani 1 1 d . . . . .
H13 H 0.535122 0.356169 0.008011 0.035 Uiso 1 1 calc R U . . .
C9 C 0.6846(4) 0.3363(2) 0.06160(14) 0.0277(8) Uani 1 1 d . . . . .
C10 C 0.6193(5) 0.2635(2) 0.06619(15) 0.0318(8) Uani 1 1 d . . . . .
H14 H 0.532583 0.241470 0.045986 0.038 Uiso 1 1 calc R U . . .
C11 C 0.6788(5) 0.2248(2) 0.09904(16) 0.0365(9) Uani 1 1 d . . . . .
H15 H 0.634433 0.176044 0.101617 0.044 Uiso 1 1 calc R U . . .
C12 C 0.8073(5) 0.2578(2) 0.12933(16) 0.0357(9) Uani 1 1 d . . . . .
H16 H 0.848227 0.230926 0.152430 0.043 Uiso 1 1 calc R U . . .
C13 C 0.8734(4) 0.3278(2) 0.12587(14) 0.0312(8) Uani 1 1 d . . . . .
H17 H 0.959060 0.348786 0.146763 0.037 Uiso 1 1 calc R U . . .
C14 C 0.8165(4) 0.3695(2) 0.09167(13) 0.0264(7) Uani 1 1 d . . . . .
C15 C 0.8844(4) 0.44208(19) 0.08591(13) 0.0244(7) Uani 1 1 d . . . . .
C16 C 1.0263(4) 0.4744(2) 0.11577(13) 0.0260(7) Uani 1 1 d . . . . .
H18 H 1.115951 0.445940 0.116023 0.031 Uiso 1 1 calc R U . . .
N1 N 1.0465(3) 0.53478(16) 0.14124(11) 0.0262(6) Uani 1 1 d . . . . .
N2 N 0.9207(3) 0.57865(16) 0.14316(12) 0.0263(6) Uani 1 1 d . . . . .
H19 H 0.829(6) 0.568(2) 0.1231(17) 0.031(11) Uiso 1 1 d . . . . .
C17 C 0.9370(4) 0.64125(19) 0.17239(13) 0.0258(7) Uani 1 1 d . . . . .
O2 O 1.0596(3) 0.66052(14) 0.19660(10) 0.0303(6) Uani 1 1 d . . . . .
C18 C 0.7888(4) 0.68226(19) 0.17185(14) 0.0287(8) Uani 1 1 d . . . . .
H20 H 0.703051 0.659650 0.191757 0.034 Uiso 1 1 calc R U . . .
H21 H 0.743939 0.678128 0.139707 0.034 Uiso 1 1 calc R U . . .
C19 C 0.8259(5) 0.7626(2) 0.18894(15) 0.0319(8) Uani 1 1 d . . . . .
H22 H 0.877393 0.766753 0.220283 0.038 Uiso 1 1 calc R U . . .
H23 H 0.720950 0.784686 0.191839 0.038 Uiso 1 1 calc R U . . .
C20 C 0.9393(5) 0.8051(2) 0.15691(15) 0.0330(8) Uani 1 1 d . . . . .
H24 H 1.047861 0.786065 0.156347 0.040 Uiso 1 1 calc R U . . .
H25 H 0.892888 0.797307 0.124902 0.040 Uiso 1 1 calc R U . . .
C21 C 0.9632(5) 0.8861(2) 0.17166(16) 0.0356(9) Uani 1 1 d . . . . .
H26 H 0.995314 0.893608 0.204983 0.043 Uiso 1 1 calc R U . . .
H27 H 0.857161 0.906341 0.168165 0.043 Uiso 1 1 calc R U . . .
C22 C 1.0941(5) 0.9273(2) 0.14336(17) 0.0381(9) Uani 1 1 d . . . . .
H28 H 1.060276 0.920491 0.110156 0.046 Uiso 1 1 calc R U . . .
H29 H 1.199039 0.905885 0.146177 0.046 Uiso 1 1 calc R U . . .
C23 C 1.1238(6) 1.0085(2) 0.1582(2) 0.0461(11) Uani 1 1 d . . . . .
H30 H 1.021311 1.030888 0.153474 0.055 Uiso 1 1 calc R U . . .
H31 H 1.152015 1.015749 0.191830 0.055 Uiso 1 1 calc R U . . .
C24 C 1.2615(6) 1.0460(3) 0.1311(2) 0.0546(13) Uani 1 1 d . . . . .
H32 H 1.363454 1.024121 0.135816 0.082 Uiso 1 1 calc R U . . .
H33 H 1.277627 1.097697 0.141966 0.082 Uiso 1 1 calc R U . . .
H34 H 1.232440 1.040324 0.097875 0.082 Uiso 1 1 calc R U . . .
O3 O 0.4249(3) 0.58207(14) 0.23034(10) 0.0282(6) Uani 1 1 d . . . . .
C25 C 0.3586(4) 0.6371(2) 0.26102(14) 0.0280(8) Uani 1 1 d . . . . .
H35 H 0.394311 0.633985 0.293504 0.034 Uiso 1 1 calc R U . . .
H36 H 0.236753 0.630410 0.259623 0.034 Uiso 1 1 calc R U . . .
C26 C 0.4222(4) 0.7096(2) 0.24501(14) 0.0295(8) Uani 1 1 d . . . . .
H37 H 0.408686 0.707539 0.210798 0.035 Uiso 1 1 calc R U . . .
H38 H 0.541321 0.719434 0.252383 0.035 Uiso 1 1 calc R U . . .
C27 C 0.3344(4) 0.77164(19) 0.26749(14) 0.0282(8) Uani 1 1 d . . . . .
H39 H 0.214012 0.757917 0.265374 0.034 Uiso 1 1 calc R U . . .
H40 H 0.365675 0.780215 0.300854 0.034 Uiso 1 1 calc R U . . .
C28 C 0.3771(5) 0.8413(2) 0.24421(16) 0.0380(9) Uani 1 1 d . . . . .
H41 H 0.498126 0.853448 0.245184 0.046 Uiso 1 1 calc R U . . .
H42 H 0.342421 0.832733 0.211103 0.046 Uiso 1 1 calc R U . . .
C29 C 0.2973(5) 0.9055(2) 0.26660(18) 0.0422(10) Uani 1 1 d . . . . .
H43 H 0.178879 0.891873 0.269562 0.063 Uiso 1 1 calc R U . . .
H44 H 0.315361 0.946154 0.247194 0.063 Uiso 1 1 calc R U . . .
H45 H 0.346201 0.920122 0.297524 0.063 Uiso 1 1 calc R U . . .
C30 C 0.3506(4) 0.5131(2) 0.22882(14) 0.0263(7) Uani 1 1 d . . . . .
C31 C 0.2367(4) 0.4896(2) 0.26261(13) 0.0272(7) Uani 1 1 d . . . . .
H46 H 0.207308 0.523339 0.287088 0.033 Uiso 1 1 calc R U . . .
C32 C 0.1684(4) 0.4192(2) 0.26048(14) 0.0290(8) Uani 1 1 d . . . . .
H47 H 0.092014 0.404374 0.283419 0.035 Uiso 1 1 calc R U . . .
C33 C 0.2107(4) 0.3681(2) 0.22426(14) 0.0271(7) Uani 1 1 d . . . . .
C34 C 0.1422(4) 0.2941(2) 0.22196(15) 0.0304(8) Uani 1 1 d . . . . .
H48 H 0.065381 0.278774 0.244692 0.037 Uiso 1 1 calc R U . . .
C35 C 0.1859(5) 0.2450(2) 0.18741(15) 0.0324(8) Uani 1 1 d . . . . .
H49 H 0.140890 0.195666 0.186296 0.039 Uiso 1 1 calc R U . . .
C36 C 0.2989(5) 0.2681(2) 0.15322(15) 0.0320(8) Uani 1 1 d . . . . .
H50 H 0.328787 0.233648 0.129241 0.038 Uiso 1 1 calc R U . . .
C37 C 0.3660(4) 0.3388(2) 0.15392(14) 0.0297(8) Uani 1 1 d . . . . .
H51 H 0.439501 0.353144 0.130181 0.036 Uiso 1 1 calc R U . . .
C38 C 0.3256(4) 0.3909(2) 0.19024(13) 0.0258(7) Uani 1 1 d . . . . .
C39 C 0.3959(4) 0.46482(19) 0.19266(13) 0.0253(7) Uani 1 1 d . . . . .
C40 C 0.5274(4) 0.48599(19) 0.15975(14) 0.0265(7) Uani 1 1 d . . . . .
H52 H 0.616027 0.456815 0.158845 0.032 Uiso 1 1 calc R U . . .
N3 N 0.5430(3) 0.53636(16) 0.13238(11) 0.0264(6) Uani 1 1 d . . . . .
N4 N 0.4185(3) 0.58013(17) 0.13057(12) 0.0264(6) Uani 1 1 d . . . . .
H53 H 0.330(5) 0.572(2) 0.1491(16) 0.023(10) Uiso 1 1 d . . . . .
C41 C 0.4317(4) 0.63259(19) 0.09983(13) 0.0254(7) Uani 1 1 d . . . . .
O4 O 0.5497(3) 0.64253(14) 0.07457(9) 0.0285(6) Uani 1 1 d . . . . .
C42 C 0.2871(4) 0.6767(2) 0.10146(15) 0.0304(8) Uani 1 1 d . . . . .
H54 H 0.263542 0.691540 0.134384 0.036 Uiso 1 1 calc R U . . .
H55 H 0.189240 0.645720 0.088143 0.036 Uiso 1 1 calc R U . . .
C43 C 0.3136(4) 0.7443(2) 0.07529(14) 0.0293(8) Uani 1 1 d . . . . .
H56 H 0.209728 0.767218 0.075590 0.035 Uiso 1 1 calc R U . . .
H57 H 0.337899 0.729294 0.042441 0.035 Uiso 1 1 calc R U . . .
C44 C 0.4522(5) 0.8013(2) 0.09462(15) 0.0322(8) Uani 1 1 d . . . . .
H58 H 0.427083 0.818108 0.127106 0.039 Uiso 1 1 calc R U . . .
H59 H 0.556535 0.778742 0.094950 0.039 Uiso 1 1 calc R U . . .
C45 C 0.4739(5) 0.8660(2) 0.06587(16) 0.0368(9) Uani 1 1 d . . . . .
H60 H 0.373020 0.891157 0.068276 0.044 Uiso 1 1 calc R U . . .
H61 H 0.486199 0.848239 0.032802 0.044 Uiso 1 1 calc R U . . .
C46 C 0.6213(5) 0.9205(2) 0.0806(2) 0.0439(11) Uani 1 1 d . . . . .
H62 H 0.610026 0.937975 0.113729 0.053 Uiso 1 1 calc R U . . .
H63 H 0.722632 0.895742 0.077661 0.053 Uiso 1 1 calc R U . . .
C47 C 0.6395(6) 0.9852(3) 0.0520(3) 0.0606(15) Uani 1 1 d . . . . .
H64 H 0.638661 0.967260 0.018587 0.073 Uiso 1 1 calc R U . . .
H65 H 0.542866 1.012557 0.057428 0.073 Uiso 1 1 calc R U . . .
C48 C 0.7903(8) 1.0352(4) 0.0623(4) 0.088(3) Uani 1 1 d . . . . .
H66 H 0.793541 1.052769 0.095355 0.133 Uiso 1 1 calc R U . . .
H67 H 0.790536 1.076540 0.043474 0.133 Uiso 1 1 calc R U . . .
H68 H 0.887036 1.009678 0.054790 0.133 Uiso 1 1 calc R U . . .
O5 O 0.5660(3) 0.35145(14) 0.28817(10) 0.0283(6) Uani 1 1 d . . . . .
C49 C 0.6291(4) 0.2990(2) 0.25519(14) 0.0277(8) Uani 1 1 d . . . . .
H69 H 0.750755 0.303504 0.257235 0.033 Uiso 1 1 calc R U . . .
H70 H 0.596855 0.307271 0.223190 0.033 Uiso 1 1 calc R U . . .
C50 C 0.5587(4) 0.2241(2) 0.26630(14) 0.0299(8) Uani 1 1 d . . . . .
H71 H 0.437682 0.218844 0.261836 0.036 Uiso 1 1 calc R U . . .
H72 H 0.582289 0.218105 0.299301 0.036 Uiso 1 1 calc R U . . .
C51 C 0.6320(5) 0.1654(2) 0.23521(15) 0.0331(8) Uani 1 1 d . . . . .
H73 H 0.607607 0.171973 0.202334 0.040 Uiso 1 1 calc R U . . .
H74 H 0.753126 0.171954 0.239406 0.040 Uiso 1 1 calc R U . . .
C52 C 0.5687(6) 0.0888(2) 0.24469(19) 0.0442(11) Uani 1 1 d . . . . .
H75 H 0.447962 0.081554 0.239702 0.053 Uiso 1 1 calc R U . . .
H76 H 0.591261 0.082188 0.277660 0.053 Uiso 1 1 calc R U . . .
C53 C 0.6473(6) 0.0322(2) 0.2137(2) 0.0504(12) Uani 1 1 d . . . . .
H77 H 0.627765 0.039252 0.181022 0.076 Uiso 1 1 calc R U . . .
H78 H 0.599006 -0.016375 0.220105 0.076 Uiso 1 1 calc R U . . .
H79 H 0.766086 0.037032 0.220044 0.076 Uiso 1 1 calc R U . . .
C54 C 0.6382(4) 0.42089(19) 0.29018(14) 0.0257(7) Uani 1 1 d . . . . .
C55 C 0.7547(4) 0.4445(2) 0.25665(14) 0.0289(8) Uani 1 1 d . . . . .
H80 H 0.786311 0.410961 0.232390 0.035 Uiso 1 1 calc R U . . .
C56 C 0.8211(4) 0.5155(2) 0.25929(14) 0.0276(7) Uani 1 1 d . . . . .
H81 H 0.897180 0.530824 0.236393 0.033 Uiso 1 1 calc R U . . .
C57 C 0.7785(4) 0.5665(2) 0.29561(14) 0.0272(8) Uani 1 1 d . . . . .
C58 C 0.8502(4) 0.6396(2) 0.29895(15) 0.0308(8) Uani 1 1 d . . . . .
H82 H 0.927175 0.655289 0.276363 0.037 Uiso 1 1 calc R U . . .
C59 C 0.8088(4) 0.6877(2) 0.33469(15) 0.0320(8) Uani 1 1 d . . . . .
H83 H 0.856679 0.736689 0.336824 0.038 Uiso 1 1 calc R U . . .
C60 C 0.6950(4) 0.6642(2) 0.36834(15) 0.0310(8) Uani 1 1 d . . . . .
H84 H 0.667586 0.697839 0.393143 0.037 Uiso 1 1 calc R U . . .
C61 C 0.6232(4) 0.5941(2) 0.36593(14) 0.0296(8) Uani 1 1 d . . . . .
H85 H 0.546570 0.579560 0.388888 0.036 Uiso 1 1 calc R U . . .
C62 C 0.6628(4) 0.54287(19) 0.32932(13) 0.0255(7) Uani 1 1 d . . . . .
C63 C 0.5924(4) 0.46859(19) 0.32599(13) 0.0247(7) Uani 1 1 d . . . . .
C64 C 0.4591(4) 0.44699(18) 0.35861(13) 0.0252(7) Uani 1 1 d . . . . .
H86 H 0.372359 0.477232 0.360357 0.030 Uiso 1 1 calc R U . . .
N5 N 0.4409(3) 0.39461(16) 0.38479(11) 0.0253(6) Uani 1 1 d . . . . .
N6 N 0.5631(3) 0.34972(16) 0.38597(11) 0.0240(6) Uani 1 1 d . . . . .
H87 H 0.647(6) 0.359(2) 0.3682(17) 0.030(11) Uiso 1 1 d . . . . .
C65 C 0.5480(4) 0.29630(18) 0.41547(13) 0.0244(7) Uani 1 1 d . . . . .
O6 O 0.4276(3) 0.28567(14) 0.44043(10) 0.0283(6) Uani 1 1 d . . . . .
C66 C 0.6937(4) 0.25297(19) 0.41519(14) 0.0278(8) Uani 1 1 d . . . . .
H88 H 0.785587 0.282259 0.432828 0.033 Uiso 1 1 calc R U . . .
H89 H 0.729924 0.243559 0.382687 0.033 Uiso 1 1 calc R U . . .
C67 C 0.6579(4) 0.1810(2) 0.43607(15) 0.0296(8) Uani 1 1 d . . . . .
H90 H 0.616960 0.190321 0.468090 0.036 Uiso 1 1 calc R U . . .
H91 H 0.761979 0.158679 0.438232 0.036 Uiso 1 1 calc R U . . .
C68 C 0.5321(4) 0.1273(2) 0.40840(14) 0.0298(8) Uani 1 1 d . . . . .
H92 H 0.425697 0.148067 0.407940 0.036 Uiso 1 1 calc R U . . .
H93 H 0.569529 0.119977 0.375867 0.036 Uiso 1 1 calc R U . . .
C69 C 0.5062(5) 0.0539(2) 0.42847(15) 0.0329(8) Uani 1 1 d . . . . .
H94 H 0.609635 0.030648 0.425608 0.039 Uiso 1 1 calc R U . . .
H95 H 0.481683 0.061798 0.462018 0.039 Uiso 1 1 calc R U . . .
C70 C 0.3677(5) 0.0026(2) 0.40466(16) 0.0325(8) Uani 1 1 d . . . . .
H96 H 0.265830 0.027040 0.406253 0.039 Uiso 1 1 calc R U . . .
H97 H 0.394963 -0.006660 0.371384 0.039 Uiso 1 1 calc R U . . .
C71 C 0.3335(5) -0.0698(2) 0.42506(17) 0.0378(9) Uani 1 1 d . . . . .
H98 H 0.305632 -0.060881 0.458306 0.045 Uiso 1 1 calc R U . . .
H99 H 0.434882 -0.094629 0.423384 0.045 Uiso 1 1 calc R U . . .
C72 C 0.1940(5) -0.1197(2) 0.40031(19) 0.0416(10) Uani 1 1 d . . . . .
H100 H 0.094994 -0.094334 0.399924 0.062 Uiso 1 1 calc R U . . .
H101 H 0.171175 -0.163384 0.416794 0.062 Uiso 1 1 calc R U . . .
H102 H 0.226022 -0.133489 0.368287 0.062 Uiso 1 1 calc R U . . .
O7 O 1.0679(3) 0.38024(13) 0.47267(9) 0.0262(5) Uani 1 1 d . . . . .
C73 C 1.1355(4) 0.33551(19) 0.50442(13) 0.0259(7) Uani 1 1 d . . . . .
H103 H 1.104713 0.350471 0.536758 0.031 Uiso 1 1 calc R U . . .
H104 H 1.257063 0.340412 0.502526 0.031 Uiso 1 1 calc R U . . .
C74 C 1.0658(4) 0.25753(19) 0.49065(14) 0.0280(8) Uani 1 1 d . . . . .
H105 H 1.080214 0.246172 0.456815 0.034 Uiso 1 1 calc R U . . .
H106 H 0.946316 0.251951 0.497032 0.034 Uiso 1 1 calc R U . . .
C75 C 1.1496(4) 0.2041(2) 0.51704(14) 0.0295(8) Uani 1 1 d . . . . .
H107 H 1.270458 0.214281 0.514271 0.035 Uiso 1 1 calc R U . . .
H108 H 1.122118 0.210951 0.550429 0.035 Uiso 1 1 calc R U . . .
C76 C 1.0974(5) 0.1261(2) 0.49877(15) 0.0350(9) Uani 1 1 d . . . . .
H109 H 1.125105 0.119401 0.465378 0.042 Uiso 1 1 calc R U . . .
H110 H 0.976508 0.116158 0.501393 0.042 Uiso 1 1 calc R U . . .
C77 C 1.1793(6) 0.0718(2) 0.52473(18) 0.0424(10) Uani 1 1 d . . . . .
H111 H 1.298953 0.080027 0.521222 0.064 Uiso 1 1 calc R U . . .
H112 H 1.139832 0.022369 0.511895 0.064 Uiso 1 1 calc R U . . .
H113 H 1.151975 0.077906 0.557805 0.064 Uiso 1 1 calc R U . . .
C78 C 1.1431(4) 0.44830(19) 0.46962(13) 0.0252(7) Uani 1 1 d . . . . .
C79 C 1.2612(4) 0.4821(2) 0.50314(14) 0.0269(7) Uani 1 1 d . . . . .
H114 H 1.292753 0.456493 0.528120 0.032 Uiso 1 1 calc R U . . .
C80 C 1.3292(4) 0.5517(2) 0.49933(13) 0.0263(7) Uani 1 1 d . . . . .
H115 H 1.407606 0.574028 0.521994 0.032 Uiso 1 1 calc R U . . .
C81 C 1.2857(4) 0.59112(19) 0.46261(14) 0.0265(7) Uani 1 1 d . . . . .
C82 C 1.3574(4) 0.6631(2) 0.45804(14) 0.0297(8) Uani 1 1 d . . . . .
H116 H 1.436088 0.685749 0.480531 0.036 Uiso 1 1 calc R U . . .
C83 C 1.3155(5) 0.7005(2) 0.42199(16) 0.0325(8) Uani 1 1 d . . . . .
H117 H 1.365067 0.748528 0.419496 0.039 Uiso 1 1 calc R U . . .
C84 C 1.1983(5) 0.6676(2) 0.38848(15) 0.0310(8) Uani 1 1 d . . . . .
H118 H 1.169361 0.693443 0.363329 0.037 Uiso 1 1 calc R U . . .
C85 C 1.1258(4) 0.59815(19) 0.39205(14) 0.0262(7) Uani 1 1 d . . . . .
H119 H 1.046365 0.576903 0.369372 0.031 Uiso 1 1 calc R U . . .
C86 C 1.1670(4) 0.55772(19) 0.42871(13) 0.0245(7) Uani 1 1 d . . . . .
C87 C 1.0955(4) 0.48507(18) 0.43295(13) 0.0231(7) Uani 1 1 d . . . . .
C88 C 0.9603(4) 0.45367(18) 0.40062(13) 0.0247(7) Uani 1 1 d . . . . .
H120 H 0.872925 0.483125 0.398778 0.030 Uiso 1 1 calc R U . . .
N7 N 0.9406(3) 0.39354(15) 0.37464(11) 0.0245(6) Uani 1 1 d . . . . .
N8 N 1.0626(3) 0.34863(15) 0.37400(11) 0.0236(6) Uani 1 1 d . . . . .
H121 H 1.157(7) 0.365(3) 0.3908(19) 0.044(14) Uiso 1 1 d . . . . .
C89 C 1.0451(4) 0.28672(18) 0.34403(12) 0.0227(7) Uani 1 1 d . . . . .
O8 O 0.9236(3) 0.26956(13) 0.31919(10) 0.0281(6) Uani 1 1 d . . . . .
C90 C 1.1891(4) 0.24290(19) 0.34441(14) 0.0278(8) Uani 1 1 d . . . . .
H122 H 1.222246 0.239412 0.377074 0.033 Uiso 1 1 calc R U . . .
H123 H 1.283053 0.268630 0.328911 0.033 Uiso 1 1 calc R U . . .
C91 C 1.1530(4) 0.16646(19) 0.32015(14) 0.0289(8) Uani 1 1 d . . . . .
H124 H 1.115498 0.170015 0.287874 0.035 Uiso 1 1 calc R U . . .
H125 H 1.256318 0.143083 0.318449 0.035 Uiso 1 1 calc R U . . .
C92 C 1.0237(5) 0.11847(19) 0.34413(14) 0.0295(8) Uani 1 1 d . . . . .
H126 H 0.919309 0.141055 0.345332 0.035 Uiso 1 1 calc R U . . .
H127 H 1.060019 0.115065 0.376528 0.035 Uiso 1 1 calc R U . . .
C93 C 0.9929(5) 0.0419(2) 0.31911(15) 0.0327(8) Uani 1 1 d . . . . .
H128 H 0.963529 0.045686 0.286189 0.039 Uiso 1 1 calc R U . . .
H129 H 1.095992 0.018471 0.319546 0.039 Uiso 1 1 calc R U . . .
C94 C 0.8560(5) -0.0061(2) 0.34099(16) 0.0338(9) Uani 1 1 d . . . . .
H130 H 0.886184 -0.009974 0.373831 0.041 Uiso 1 1 calc R U . . .
H131 H 0.753551 0.017928 0.340919 0.041 Uiso 1 1 calc R U . . .
C95 C 0.8219(5) -0.0818(2) 0.31654(18) 0.0393(9) Uani 1 1 d . . . . .
H132 H 0.924211 -0.105914 0.316375 0.047 Uiso 1 1 calc R U . . .
H133 H 0.790079 -0.078174 0.283792 0.047 Uiso 1 1 calc R U . . .
C96 C 0.6860(5) -0.1286(2) 0.3394(2) 0.0453(11) Uani 1 1 d . . . . .
H134 H 0.720425 -0.135764 0.371042 0.068 Uiso 1 1 calc R U . . .
H135 H 0.665118 -0.175851 0.321174 0.068 Uiso 1 1 calc R U . . .
H136 H 0.585229 -0.104399 0.340609 0.068 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.352(4) . ?
O1 C1 1.439(4) . ?
C1 C2 1.510(5) . ?
C1 H1 0.9900 . ?
C1 H2 0.9900 . ?
C2 C3 1.509(5) . ?
C2 H3 0.9900 . ?
C2 H4 0.9900 . ?
C3 C4 1.528(6) . ?
C3 H5 0.9900 . ?
C3 H6 0.9900 . ?
C4 C5 1.504(7) . ?
C4 H7 0.9900 . ?
C4 H8 0.9900 . ?
C5 H9 0.9800 . ?
C5 H10 0.9800 . ?
C5 H11 0.9800 . ?
C6 C15 1.389(5) . ?
C6 C7 1.423(5) . ?
C7 C8 1.359(5) . ?
C7 H12 0.9500 . ?
C8 C9 1.417(5) . ?
C8 H13 0.9500 . ?
C9 C10 1.420(5) . ?
C9 C14 1.432(5) . ?
C10 C11 1.361(6) . ?
C10 H14 0.9500 . ?
C11 C12 1.416(6) . ?
C11 H15 0.9500 . ?
C12 C13 1.368(5) . ?
C12 H16 0.9500 . ?
C13 C14 1.417(5) . ?
C13 H17 0.9500 . ?
C14 C15 1.429(5) . ?
C15 C16 1.484(5) . ?
C16 N1 1.280(5) . ?
C16 H18 0.9500 . ?
N1 N2 1.378(4) . ?
N2 C17 1.369(5) . ?
N2 H19 0.94(5) . ?
C17 O2 1.223(4) . ?
C17 C18 1.500(5) . ?
C18 C19 1.530(5) . ?
C18 H20 0.9900 . ?
C18 H21 0.9900 . ?
C19 C20 1.523(5) . ?
C19 H22 0.9900 . ?
C19 H23 0.9900 . ?
C20 C21 1.519(5) . ?
C20 H24 0.9900 . ?
C20 H25 0.9900 . ?
C21 C22 1.531(6) . ?
C21 H26 0.9900 . ?
C21 H27 0.9900 . ?
C22 C23 1.525(6) . ?
C22 H28 0.9900 . ?
C22 H29 0.9900 . ?
C23 C24 1.517(7) . ?
C23 H30 0.9900 . ?
C23 H31 0.9900 . ?
C24 H32 0.9800 . ?
C24 H33 0.9800 . ?
C24 H34 0.9800 . ?
O3 C30 1.357(4) . ?
O3 C25 1.443(4) . ?
C25 C26 1.507(5) . ?
C25 H35 0.9900 . ?
C25 H36 0.9900 . ?
C26 C27 1.520(5) . ?
C26 H37 0.9900 . ?
C26 H38 0.9900 . ?
C27 C28 1.522(6) . ?
C27 H39 0.9900 . ?
C27 H40 0.9900 . ?
C28 C29 1.517(6) . ?
C28 H41 0.9900 . ?
C28 H42 0.9900 . ?
C29 H43 0.9800 . ?
C29 H44 0.9800 . ?
C29 H45 0.9800 . ?
C30 C39 1.391(5) . ?
C30 C31 1.415(5) . ?
C31 C32 1.364(5) . ?
C31 H46 0.9500 . ?
C32 C33 1.417(5) . ?
C32 H47 0.9500 . ?
C33 C38 1.421(5) . ?
C33 C34 1.426(5) . ?
C34 C35 1.364(6) . ?
C34 H48 0.9500 . ?
C35 C36 1.416(6) . ?
C35 H49 0.9500 . ?
C36 C37 1.368(5) . ?
C36 H50 0.9500 . ?
C37 C38 1.426(5) . ?
C37 H51 0.9500 . ?
C38 C39 1.428(5) . ?
C39 C40 1.481(5) . ?
C40 N3 1.276(5) . ?
C40 H52 0.9500 . ?
N3 N4 1.374(4) . ?
N4 C41 1.374(5) . ?
N4 H53 0.91(5) . ?
C41 O4 1.218(4) . ?
C41 C42 1.509(5) . ?
C42 C43 1.521(5) . ?
C42 H54 0.9900 . ?
C42 H55 0.9900 . ?
C43 C44 1.533(5) . ?
C43 H56 0.9900 . ?
C43 H57 0.9900 . ?
C44 C45 1.520(6) . ?
C44 H58 0.9900 . ?
C44 H59 0.9900 . ?
C45 C46 1.522(6) . ?
C45 H60 0.9900 . ?
C45 H61 0.9900 . ?
C46 C47 1.515(7) . ?
C46 H62 0.9900 . ?
C46 H63 0.9900 . ?
C47 C48 1.475(8) . ?
C47 H64 0.9900 . ?
C47 H65 0.9900 . ?
C48 H66 0.9800 . ?
C48 H67 0.9800 . ?
C48 H68 0.9800 . ?
O5 C54 1.358(4) . ?
O5 C49 1.437(4) . ?
C49 C50 1.511(5) . ?
C49 H69 0.9900 . ?
C49 H70 0.9900 . ?
C50 C51 1.523(5) . ?
C50 H71 0.9900 . ?
C50 H72 0.9900 . ?
C51 C52 1.513(6) . ?
C51 H73 0.9900 . ?
C51 H74 0.9900 . ?
C52 C53 1.516(6) . ?
C52 H75 0.9900 . ?
C52 H76 0.9900 . ?
C53 H77 0.9800 . ?
C53 H78 0.9800 . ?
C53 H79 0.9800 . ?
C54 C63 1.379(5) . ?
C54 C55 1.424(5) . ?
C55 C56 1.368(5) . ?
C55 H80 0.9500 . ?
C56 C57 1.419(5) . ?
C56 H81 0.9500 . ?
C57 C58 1.417(5) . ?
C57 C62 1.423(5) . ?
C58 C59 1.370(6) . ?
C58 H82 0.9500 . ?
C59 C60 1.412(6) . ?
C59 H83 0.9500 . ?
C60 C61 1.369(5) . ?
C60 H84 0.9500 . ?
C61 C62 1.419(5) . ?
C61 H85 0.9500 . ?
C62 C63 1.434(5) . ?
C63 C64 1.488(5) . ?
C64 N5 1.283(5) . ?
C64 H86 0.9500 . ?
N5 N6 1.371(4) . ?
N6 C65 1.363(5) . ?
N6 H87 0.87(5) . ?
C65 O6 1.230(4) . ?
C65 C66 1.508(5) . ?
C66 C67 1.519(5) . ?
C66 H88 0.9900 . ?
C66 H89 0.9900 . ?
C67 C68 1.525(5) . ?
C67 H90 0.9900 . ?
C67 H91 0.9900 . ?
C68 C69 1.526(5) . ?
C68 H92 0.9900 . ?
C68 H93 0.9900 . ?
C69 C70 1.519(5) . ?
C69 H94 0.9900 . ?
C69 H95 0.9900 . ?
C70 C71 1.518(6) . ?
C70 H96 0.9900 . ?
C70 H97 0.9900 . ?
C71 C72 1.524(6) . ?
C71 H98 0.9900 . ?
C71 H99 0.9900 . ?
C72 H100 0.9800 . ?
C72 H101 0.9800 . ?
C72 H102 0.9800 . ?
O7 C78 1.358(4) . ?
O7 C73 1.440(4) . ?
C73 C74 1.518(5) . ?
C73 H103 0.9900 . ?
C73 H104 0.9900 . ?
C74 C75 1.524(5) . ?
C74 H105 0.9900 . ?
C74 H106 0.9900 . ?
C75 C76 1.514(5) . ?
C75 H107 0.9900 . ?
C75 H108 0.9900 . ?
C76 C77 1.521(6) . ?
C76 H109 0.9900 . ?
C76 H110 0.9900 . ?
C77 H111 0.9800 . ?
C77 H112 0.9800 . ?
C77 H113 0.9800 . ?
C78 C87 1.388(5) . ?
C78 C79 1.420(5) . ?
C79 C80 1.368(5) . ?
C79 H114 0.9500 . ?
C80 C81 1.408(5) . ?
C80 H115 0.9500 . ?
C81 C82 1.422(5) . ?
C81 C86 1.429(5) . ?
C82 C83 1.365(6) . ?
C82 H116 0.9500 . ?
C83 C84 1.411(6) . ?
C83 H117 0.9500 . ?
C84 C85 1.375(5) . ?
C84 H118 0.9500 . ?
C85 C86 1.413(5) . ?
C85 H119 0.9500 . ?
C86 C87 1.430(5) . ?
C87 C88 1.480(5) . ?
C88 N7 1.284(5) . ?
C88 H120 0.9500 . ?
N7 N8 1.367(4) . ?
N8 C89 1.371(5) . ?
N8 H121 0.92(6) . ?
C89 O8 1.220(4) . ?
C89 C90 1.503(5) . ?
C90 C91 1.526(5) . ?
C90 H122 0.9900 . ?
C90 H123 0.9900 . ?
C91 C92 1.519(5) . ?
C91 H124 0.9900 . ?
C91 H125 0.9900 . ?
C92 C93 1.532(5) . ?
C92 H126 0.9900 . ?
C92 H127 0.9900 . ?
C93 C94 1.530(5) . ?
C93 H128 0.9900 . ?
C93 H129 0.9900 . ?
C94 C95 1.516(5) . ?
C94 H130 0.9900 . ?
C94 H131 0.9900 . ?
C95 C96 1.525(6) . ?
C95 H132 0.9900 . ?
C95 H133 0.9900 . ?
C96 H134 0.9800 . ?
C96 H135 0.9800 . ?
C96 H136 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O1 C1 118.3(3) . . ?
O1 C1 C2 107.9(3) . . ?
O1 C1 H1 110.1 . . ?
C2 C1 H1 110.1 . . ?
O1 C1 H2 110.1 . . ?
C2 C1 H2 110.1 . . ?
H1 C1 H2 108.4 . . ?
C1 C2 C3 112.0(3) . . ?
C1 C2 H3 109.2 . . ?
C3 C2 H3 109.2 . . ?
C1 C2 H4 109.2 . . ?
C3 C2 H4 109.2 . . ?
H3 C2 H4 107.9 . . ?
C2 C3 C4 113.2(3) . . ?
C2 C3 H5 108.9 . . ?
C4 C3 H5 108.9 . . ?
C2 C3 H6 108.9 . . ?
C4 C3 H6 108.9 . . ?
H5 C3 H6 107.8 . . ?
C5 C4 C3 112.6(4) . . ?
C5 C4 H7 109.1 . . ?
C3 C4 H7 109.1 . . ?
C5 C4 H8 109.1 . . ?
C3 C4 H8 109.1 . . ?
H7 C4 H8 107.8 . . ?
C4 C5 H9 109.5 . . ?
C4 C5 H10 109.5 . . ?
H9 C5 H10 109.5 . . ?
C4 C5 H11 109.5 . . ?
H9 C5 H11 109.5 . . ?
H10 C5 H11 109.5 . . ?
O1 C6 C15 116.6(3) . . ?
O1 C6 C7 122.9(3) . . ?
C15 C6 C7 120.5(3) . . ?
C8 C7 C6 119.8(3) . . ?
C8 C7 H12 120.1 . . ?
C6 C7 H12 120.1 . . ?
C7 C8 C9 122.0(3) . . ?
C7 C8 H13 119.0 . . ?
C9 C8 H13 119.0 . . ?
C10 C9 C8 121.9(3) . . ?
C10 C9 C14 119.6(4) . . ?
C8 C9 C14 118.5(3) . . ?
C11 C10 C9 121.1(4) . . ?
C11 C10 H14 119.4 . . ?
C9 C10 H14 119.4 . . ?
C10 C11 C12 119.5(4) . . ?
C10 C11 H15 120.3 . . ?
C12 C11 H15 120.3 . . ?
C13 C12 C11 121.0(4) . . ?
C13 C12 H16 119.5 . . ?
C11 C12 H16 119.5 . . ?
C12 C13 C14 121.2(4) . . ?
C12 C13 H17 119.4 . . ?
C14 C13 H17 119.4 . . ?
C15 C14 C13 123.3(3) . . ?
C15 C14 C9 119.1(3) . . ?
C13 C14 C9 117.6(3) . . ?
C6 C15 C14 119.9(3) . . ?
C6 C15 C16 121.4(3) . . ?
C14 C15 C16 118.5(3) . . ?
N1 C16 C15 130.0(3) . . ?
N1 C16 H18 115.0 . . ?
C15 C16 H18 115.0 . . ?
C16 N1 N2 118.4(3) . . ?
C17 N2 N1 118.9(3) . . ?
C17 N2 H19 120(3) . . ?
N1 N2 H19 121(3) . . ?
O2 C17 N2 122.8(3) . . ?
O2 C17 C18 124.3(3) . . ?
N2 C17 C18 112.9(3) . . ?
C17 C18 C19 113.2(3) . . ?
C17 C18 H20 108.9 . . ?
C19 C18 H20 108.9 . . ?
C17 C18 H21 108.9 . . ?
C19 C18 H21 108.9 . . ?
H20 C18 H21 107.7 . . ?
C18 C19 C20 113.4(3) . . ?
C18 C19 H22 108.9 . . ?
C20 C19 H22 108.9 . . ?
C18 C19 H23 108.9 . . ?
C20 C19 H23 108.9 . . ?
H22 C19 H23 107.7 . . ?
C21 C20 C19 113.1(3) . . ?
C21 C20 H24 109.0 . . ?
C19 C20 H24 109.0 . . ?
C21 C20 H25 109.0 . . ?
C19 C20 H25 109.0 . . ?
H24 C20 H25 107.8 . . ?
C20 C21 C22 113.1(3) . . ?
C20 C21 H26 109.0 . . ?
C22 C21 H26 109.0 . . ?
C20 C21 H27 109.0 . . ?
C22 C21 H27 109.0 . . ?
H26 C21 H27 107.8 . . ?
C21 C22 C23 114.2(4) . . ?
C21 C22 H28 108.7 . . ?
C23 C22 H28 108.7 . . ?
C21 C22 H29 108.7 . . ?
C23 C22 H29 108.7 . . ?
H28 C22 H29 107.6 . . ?
C24 C23 C22 112.1(4) . . ?
C24 C23 H30 109.2 . . ?
C22 C23 H30 109.2 . . ?
C24 C23 H31 109.2 . . ?
C22 C23 H31 109.2 . . ?
H30 C23 H31 107.9 . . ?
C23 C24 H32 109.5 . . ?
C23 C24 H33 109.5 . . ?
H32 C24 H33 109.5 . . ?
C23 C24 H34 109.5 . . ?
H32 C24 H34 109.5 . . ?
H33 C24 H34 109.5 . . ?
C30 O3 C25 118.1(3) . . ?
O3 C25 C26 107.3(3) . . ?
O3 C25 H35 110.3 . . ?
C26 C25 H35 110.3 . . ?
O3 C25 H36 110.3 . . ?
C26 C25 H36 110.3 . . ?
H35 C25 H36 108.5 . . ?
C25 C26 C27 112.9(3) . . ?
C25 C26 H37 109.0 . . ?
C27 C26 H37 109.0 . . ?
C25 C26 H38 109.0 . . ?
C27 C26 H38 109.0 . . ?
H37 C26 H38 107.8 . . ?
C28 C27 C26 111.8(3) . . ?
C28 C27 H39 109.3 . . ?
C26 C27 H39 109.3 . . ?
C28 C27 H40 109.3 . . ?
C26 C27 H40 109.3 . . ?
H39 C27 H40 107.9 . . ?
C29 C28 C27 113.8(3) . . ?
C29 C28 H41 108.8 . . ?
C27 C28 H41 108.8 . . ?
C29 C28 H42 108.8 . . ?
C27 C28 H42 108.8 . . ?
H41 C28 H42 107.7 . . ?
C28 C29 H43 109.5 . . ?
C28 C29 H44 109.5 . . ?
H43 C29 H44 109.5 . . ?
C28 C29 H45 109.5 . . ?
H43 C29 H45 109.5 . . ?
H44 C29 H45 109.5 . . ?
O3 C30 C39 116.4(3) . . ?
O3 C30 C31 122.8(3) . . ?
C39 C30 C31 120.7(3) . . ?
C32 C31 C30 120.9(3) . . ?
C32 C31 H46 119.6 . . ?
C30 C31 H46 119.6 . . ?
C31 C32 C33 120.4(3) . . ?
C31 C32 H47 119.8 . . ?
C33 C32 H47 119.8 . . ?
C38 C33 C32 119.3(3) . . ?
C38 C33 C34 119.7(3) . . ?
C32 C33 C34 121.1(3) . . ?
C35 C34 C33 120.6(3) . . ?
C35 C34 H48 119.7 . . ?
C33 C34 H48 119.7 . . ?
C34 C35 C36 119.7(3) . . ?
C34 C35 H49 120.2 . . ?
C36 C35 H49 120.2 . . ?
C37 C36 C35 121.5(4) . . ?
C37 C36 H50 119.2 . . ?
C35 C36 H50 119.2 . . ?
C36 C37 C38 120.1(4) . . ?
C36 C37 H51 120.0 . . ?
C38 C37 H51 120.0 . . ?
C33 C38 C39 119.9(3) . . ?
C33 C38 C37 118.5(3) . . ?
C39 C38 C37 121.6(3) . . ?
C30 C39 C38 118.8(3) . . ?
C30 C39 C40 121.8(3) . . ?
C38 C39 C40 119.1(3) . . ?
N3 C40 C39 131.6(3) . . ?
N3 C40 H52 114.2 . . ?
C39 C40 H52 114.2 . . ?
C40 N3 N4 118.2(3) . . ?
C41 N4 N3 118.4(3) . . ?
C41 N4 H53 124(3) . . ?
N3 N4 H53 118(3) . . ?
O4 C41 N4 122.9(3) . . ?
O4 C41 C42 124.1(3) . . ?
N4 C41 C42 112.9(3) . . ?
C41 C42 C43 114.0(3) . . ?
C41 C42 H54 108.8 . . ?
C43 C42 H54 108.8 . . ?
C41 C42 H55 108.8 . . ?
C43 C42 H55 108.8 . . ?
H54 C42 H55 107.7 . . ?
C42 C43 C44 115.1(3) . . ?
C42 C43 H56 108.5 . . ?
C44 C43 H56 108.5 . . ?
C42 C43 H57 108.5 . . ?
C44 C43 H57 108.5 . . ?
H56 C43 H57 107.5 . . ?
C45 C44 C43 111.9(3) . . ?
C45 C44 H58 109.2 . . ?
C43 C44 H58 109.2 . . ?
C45 C44 H59 109.2 . . ?
C43 C44 H59 109.2 . . ?
H58 C44 H59 107.9 . . ?
C44 C45 C46 114.0(4) . . ?
C44 C45 H60 108.8 . . ?
C46 C45 H60 108.8 . . ?
C44 C45 H61 108.8 . . ?
C46 C45 H61 108.8 . . ?
H60 C45 H61 107.7 . . ?
C47 C46 C45 113.2(4) . . ?
C47 C46 H62 108.9 . . ?
C45 C46 H62 108.9 . . ?
C47 C46 H63 108.9 . . ?
C45 C46 H63 108.9 . . ?
H62 C46 H63 107.7 . . ?
C48 C47 C46 114.4(5) . . ?
C48 C47 H64 108.7 . . ?
C46 C47 H64 108.7 . . ?
C48 C47 H65 108.7 . . ?
C46 C47 H65 108.7 . . ?
H64 C47 H65 107.6 . . ?
C47 C48 H66 109.5 . . ?
C47 C48 H67 109.5 . . ?
H66 C48 H67 109.5 . . ?
C47 C48 H68 109.5 . . ?
H66 C48 H68 109.5 . . ?
H67 C48 H68 109.5 . . ?
C54 O5 C49 117.6(3) . . ?
O5 C49 C50 108.3(3) . . ?
O5 C49 H69 110.0 . . ?
C50 C49 H69 110.0 . . ?
O5 C49 H70 110.0 . . ?
C50 C49 H70 110.0 . . ?
H69 C49 H70 108.4 . . ?
C49 C50 C51 111.1(3) . . ?
C49 C50 H71 109.4 . . ?
C51 C50 H71 109.4 . . ?
C49 C50 H72 109.4 . . ?
C51 C50 H72 109.4 . . ?
H71 C50 H72 108.0 . . ?
C52 C51 C50 114.1(3) . . ?
C52 C51 H73 108.7 . . ?
C50 C51 H73 108.7 . . ?
C52 C51 H74 108.7 . . ?
C50 C51 H74 108.7 . . ?
H73 C51 H74 107.6 . . ?
C51 C52 C53 112.4(4) . . ?
C51 C52 H75 109.1 . . ?
C53 C52 H75 109.1 . . ?
C51 C52 H76 109.1 . . ?
C53 C52 H76 109.1 . . ?
H75 C52 H76 107.8 . . ?
C52 C53 H77 109.5 . . ?
C52 C53 H78 109.5 . . ?
H77 C53 H78 109.5 . . ?
C52 C53 H79 109.5 . . ?
H77 C53 H79 109.5 . . ?
H78 C53 H79 109.5 . . ?
O5 C54 C63 117.1(3) . . ?
O5 C54 C55 122.1(3) . . ?
C63 C54 C55 120.8(3) . . ?
C56 C55 C54 120.1(3) . . ?
C56 C55 H80 119.9 . . ?
C54 C55 H80 119.9 . . ?
C55 C56 C57 121.2(3) . . ?
C55 C56 H81 119.4 . . ?
C57 C56 H81 119.4 . . ?
C58 C57 C62 120.1(3) . . ?
C58 C57 C56 121.2(3) . . ?
C62 C57 C56 118.8(3) . . ?
C59 C58 C57 120.1(4) . . ?
C59 C58 H82 119.9 . . ?
C57 C58 H82 119.9 . . ?
C58 C59 C60 119.9(3) . . ?
C58 C59 H83 120.0 . . ?
C60 C59 H83 120.0 . . ?
C61 C60 C59 121.3(4) . . ?
C61 C60 H84 119.4 . . ?
C59 C60 H84 119.4 . . ?
C60 C61 C62 120.3(4) . . ?
C60 C61 H85 119.8 . . ?
C62 C61 H85 119.8 . . ?
C57 C62 C61 118.3(3) . . ?
C57 C62 C63 119.7(3) . . ?
C61 C62 C63 122.0(3) . . ?
C54 C63 C62 119.5(3) . . ?
C54 C63 C64 121.6(3) . . ?
C62 C63 C64 118.6(3) . . ?
N5 C64 C63 131.2(3) . . ?
N5 C64 H86 114.4 . . ?
C63 C64 H86 114.4 . . ?
C64 N5 N6 118.6(3) . . ?
C65 N6 N5 118.8(3) . . ?
C65 N6 H87 125(3) . . ?
N5 N6 H87 116(3) . . ?
O6 C65 N6 122.7(3) . . ?
O6 C65 C66 123.6(3) . . ?
N6 C65 C66 113.7(3) . . ?
C65 C66 C67 113.6(3) . . ?
C65 C66 H88 108.9 . . ?
C67 C66 H88 108.9 . . ?
C65 C66 H89 108.9 . . ?
C67 C66 H89 108.9 . . ?
H88 C66 H89 107.7 . . ?
C66 C67 C68 113.9(3) . . ?
C66 C67 H90 108.8 . . ?
C68 C67 H90 108.8 . . ?
C66 C67 H91 108.8 . . ?
C68 C67 H91 108.8 . . ?
H90 C67 H91 107.7 . . ?
C69 C68 C67 112.8(3) . . ?
C69 C68 H92 109.0 . . ?
C67 C68 H92 109.0 . . ?
C69 C68 H93 109.0 . . ?
C67 C68 H93 109.0 . . ?
H92 C68 H93 107.8 . . ?
C70 C69 C68 113.5(3) . . ?
C70 C69 H94 108.9 . . ?
C68 C69 H94 108.9 . . ?
C70 C69 H95 108.9 . . ?
C68 C69 H95 108.9 . . ?
H94 C69 H95 107.7 . . ?
C71 C70 C69 114.9(4) . . ?
C71 C70 H96 108.5 . . ?
C69 C70 H96 108.5 . . ?
C71 C70 H97 108.5 . . ?
C69 C70 H97 108.5 . . ?
H96 C70 H97 107.5 . . ?
C70 C71 C72 113.4(4) . . ?
C70 C71 H98 108.9 . . ?
C72 C71 H98 108.9 . . ?
C70 C71 H99 108.9 . . ?
C72 C71 H99 108.9 . . ?
H98 C71 H99 107.7 . . ?
C71 C72 H100 109.5 . . ?
C71 C72 H101 109.5 . . ?
H100 C72 H101 109.5 . . ?
C71 C72 H102 109.5 . . ?
H100 C72 H102 109.5 . . ?
H101 C72 H102 109.5 . . ?
C78 O7 C73 118.4(3) . . ?
O7 C73 C74 107.5(3) . . ?
O7 C73 H103 110.2 . . ?
C74 C73 H103 110.2 . . ?
O7 C73 H104 110.2 . . ?
C74 C73 H104 110.2 . . ?
H103 C73 H104 108.5 . . ?
C73 C74 C75 111.9(3) . . ?
C73 C74 H105 109.2 . . ?
C75 C74 H105 109.2 . . ?
C73 C74 H106 109.2 . . ?
C75 C74 H106 109.2 . . ?
H105 C74 H106 107.9 . . ?
C76 C75 C74 112.0(3) . . ?
C76 C75 H107 109.2 . . ?
C74 C75 H107 109.2 . . ?
C76 C75 H108 109.2 . . ?
C74 C75 H108 109.2 . . ?
H107 C75 H108 107.9 . . ?
C75 C76 C77 112.9(3) . . ?
C75 C76 H109 109.0 . . ?
C77 C76 H109 109.0 . . ?
C75 C76 H110 109.0 . . ?
C77 C76 H110 109.0 . . ?
H109 C76 H110 107.8 . . ?
C76 C77 H111 109.5 . . ?
C76 C77 H112 109.5 . . ?
H111 C77 H112 109.5 . . ?
C76 C77 H113 109.5 . . ?
H111 C77 H113 109.5 . . ?
H112 C77 H113 109.5 . . ?
O7 C78 C87 117.1(3) . . ?
O7 C78 C79 122.1(3) . . ?
C87 C78 C79 120.8(3) . . ?
C80 C79 C78 119.8(3) . . ?
C80 C79 H114 120.1 . . ?
C78 C79 H114 120.1 . . ?
C79 C80 C81 121.6(3) . . ?
C79 C80 H115 119.2 . . ?
C81 C80 H115 119.2 . . ?
C80 C81 C82 121.9(3) . . ?
C80 C81 C86 119.2(3) . . ?
C82 C81 C86 118.9(3) . . ?
C83 C82 C81 121.4(4) . . ?
C83 C82 H116 119.3 . . ?
C81 C82 H116 119.3 . . ?
C82 C83 C84 119.8(3) . . ?
C82 C83 H117 120.1 . . ?
C84 C83 H117 120.1 . . ?
C85 C84 C83 120.3(4) . . ?
C85 C84 H118 119.9 . . ?
C83 C84 H118 119.9 . . ?
C84 C85 C86 121.5(3) . . ?
C84 C85 H119 119.3 . . ?
C86 C85 H119 119.3 . . ?
C85 C86 C81 118.2(3) . . ?
C85 C86 C87 122.7(3) . . ?
C81 C86 C87 119.1(3) . . ?
C78 C87 C86 119.6(3) . . ?
C78 C87 C88 121.5(3) . . ?
C86 C87 C88 118.6(3) . . ?
N7 C88 C87 131.2(3) . . ?
N7 C88 H120 114.4 . . ?
C87 C88 H120 114.4 . . ?
C88 N7 N8 118.5(3) . . ?
C89 N8 N7 118.1(3) . . ?
C89 N8 H121 124(3) . . ?
N7 N8 H121 117(3) . . ?
O8 C89 N8 122.5(3) . . ?
O8 C89 C90 123.6(3) . . ?
N8 C89 C90 113.9(3) . . ?
C89 C90 C91 113.4(3) . . ?
C89 C90 H122 108.9 . . ?
C91 C90 H122 108.9 . . ?
C89 C90 H123 108.9 . . ?
C91 C90 H123 108.9 . . ?
H122 C90 H123 107.7 . . ?
C92 C91 C90 113.9(3) . . ?
C92 C91 H124 108.8 . . ?
C90 C91 H124 108.8 . . ?
C92 C91 H125 108.8 . . ?
C90 C91 H125 108.8 . . ?
H124 C91 H125 107.7 . . ?
C91 C92 C93 112.3(3) . . ?
C91 C92 H126 109.1 . . ?
C93 C92 H126 109.1 . . ?
C91 C92 H127 109.1 . . ?
C93 C92 H127 109.1 . . ?
H126 C92 H127 107.9 . . ?
C94 C93 C92 113.2(3) . . ?
C94 C93 H128 108.9 . . ?
C92 C93 H128 108.9 . . ?
C94 C93 H129 108.9 . . ?
C92 C93 H129 108.9 . . ?
H128 C93 H129 107.7 . . ?
C95 C94 C93 114.2(4) . . ?
C95 C94 H130 108.7 . . ?
C93 C94 H130 108.7 . . ?
C95 C94 H131 108.7 . . ?
C93 C94 H131 108.7 . . ?
H130 C94 H131 107.6 . . ?
C94 C95 C96 113.1(4) . . ?
C94 C95 H132 109.0 . . ?
C96 C95 H132 109.0 . . ?
C94 C95 H133 109.0 . . ?
C96 C95 H133 109.0 . . ?
H132 C95 H133 107.8 . . ?
C95 C96 H134 109.5 . . ?
C95 C96 H135 109.5 . . ?
H134 C96 H135 109.5 . . ?
C95 C96 H136 109.5 . . ?
H134 C96 H136 109.5 . . ?
H135 C96 H136 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 O1 C1 C2 170.6(3) . . . . ?
O1 C1 C2 C3 -174.9(3) . . . . ?
C1 C2 C3 C4 176.7(4) . . . . ?
C2 C3 C4 C5 -177.5(4) . . . . ?
C1 O1 C6 C15 -173.9(3) . . . . ?
C1 O1 C6 C7 7.5(5) . . . . ?
O1 C6 C7 C8 176.2(3) . . . . ?
C15 C6 C7 C8 -2.2(5) . . . . ?
C6 C7 C8 C9 -0.4(5) . . . . ?
C7 C8 C9 C10 -177.1(4) . . . . ?
C7 C8 C9 C14 1.9(5) . . . . ?
C8 C9 C10 C11 179.7(4) . . . . ?
C14 C9 C10 C11 0.7(5) . . . . ?
C9 C10 C11 C12 0.4(6) . . . . ?
C10 C11 C12 C13 -0.5(6) . . . . ?
C11 C12 C13 C14 -0.4(6) . . . . ?
C12 C13 C14 C15 -178.4(4) . . . . ?
C12 C13 C14 C9 1.5(5) . . . . ?
C10 C9 C14 C15 178.3(3) . . . . ?
C8 C9 C14 C15 -0.8(5) . . . . ?
C10 C9 C14 C13 -1.6(5) . . . . ?
C8 C9 C14 C13 179.4(3) . . . . ?
O1 C6 C15 C14 -175.3(3) . . . . ?
C7 C6 C15 C14 3.3(5) . . . . ?
O1 C6 C15 C16 -0.1(5) . . . . ?
C7 C6 C15 C16 178.4(3) . . . . ?
C13 C14 C15 C6 178.0(3) . . . . ?
C9 C14 C15 C6 -1.8(5) . . . . ?
C13 C14 C15 C16 2.8(5) . . . . ?
C9 C14 C15 C16 -177.1(3) . . . . ?
C6 C15 C16 N1 56.6(6) . . . . ?
C14 C15 C16 N1 -128.2(4) . . . . ?
C15 C16 N1 N2 0.9(6) . . . . ?
C16 N1 N2 C17 176.2(3) . . . . ?
N1 N2 C17 O2 0.9(5) . . . . ?
N1 N2 C17 C18 -178.3(3) . . . . ?
O2 C17 C18 C19 22.2(5) . . . . ?
N2 C17 C18 C19 -158.6(3) . . . . ?
C17 C18 C19 C20 66.4(5) . . . . ?
C18 C19 C20 C21 174.7(3) . . . . ?
C19 C20 C21 C22 172.5(4) . . . . ?
C20 C21 C22 C23 -178.5(4) . . . . ?
C21 C22 C23 C24 176.6(4) . . . . ?
C30 O3 C25 C26 -161.4(3) . . . . ?
O3 C25 C26 C27 167.8(3) . . . . ?
C25 C26 C27 C28 -169.1(3) . . . . ?
C26 C27 C28 C29 -177.9(3) . . . . ?
C25 O3 C30 C39 167.6(3) . . . . ?
C25 O3 C30 C31 -14.3(5) . . . . ?
O3 C30 C31 C32 -178.1(3) . . . . ?
C39 C30 C31 C32 -0.1(5) . . . . ?
C30 C31 C32 C33 0.1(5) . . . . ?
C31 C32 C33 C38 0.2(5) . . . . ?
C31 C32 C33 C34 179.1(3) . . . . ?
C38 C33 C34 C35 0.0(5) . . . . ?
C32 C33 C34 C35 -178.9(4) . . . . ?
C33 C34 C35 C36 -0.8(6) . . . . ?
C34 C35 C36 C37 0.0(6) . . . . ?
C35 C36 C37 C38 1.5(6) . . . . ?
C32 C33 C38 C39 -0.5(5) . . . . ?
C34 C33 C38 C39 -179.4(3) . . . . ?
C32 C33 C38 C37 -179.7(3) . . . . ?
C34 C33 C38 C37 1.5(5) . . . . ?
C36 C37 C38 C33 -2.2(5) . . . . ?
C36 C37 C38 C39 178.6(3) . . . . ?
O3 C30 C39 C38 178.0(3) . . . . ?
C31 C30 C39 C38 -0.1(5) . . . . ?
O3 C30 C39 C40 4.6(5) . . . . ?
C31 C30 C39 C40 -173.5(3) . . . . ?
C33 C38 C39 C30 0.4(5) . . . . ?
C37 C38 C39 C30 179.6(3) . . . . ?
C33 C38 C39 C40 174.0(3) . . . . ?
C37 C38 C39 C40 -6.8(5) . . . . ?
C30 C39 C40 N3 -58.4(6) . . . . ?
C38 C39 C40 N3 128.2(4) . . . . ?
C39 C40 N3 N4 -1.6(6) . . . . ?
C40 N3 N4 C41 -177.5(3) . . . . ?
N3 N4 C41 O4 -0.9(5) . . . . ?
N3 N4 C41 C42 -179.9(3) . . . . ?
O4 C41 C42 C43 -10.6(5) . . . . ?
N4 C41 C42 C43 168.4(3) . . . . ?
C41 C42 C43 C44 -63.6(4) . . . . ?
C42 C43 C44 C45 178.5(3) . . . . ?
C43 C44 C45 C46 -174.0(4) . . . . ?
C44 C45 C46 C47 -179.2(4) . . . . ?
C45 C46 C47 C48 -174.2(6) . . . . ?
C54 O5 C49 C50 167.4(3) . . . . ?
O5 C49 C50 C51 -175.1(3) . . . . ?
C49 C50 C51 C52 179.3(4) . . . . ?
C50 C51 C52 C53 -178.8(4) . . . . ?
C49 O5 C54 C63 -171.4(3) . . . . ?
C49 O5 C54 C55 9.4(5) . . . . ?
O5 C54 C55 C56 178.3(3) . . . . ?
C63 C54 C55 C56 -0.9(5) . . . . ?
C54 C55 C56 C57 1.2(6) . . . . ?
C55 C56 C57 C58 178.5(3) . . . . ?
C55 C56 C57 C62 -0.8(5) . . . . ?
C62 C57 C58 C59 0.2(5) . . . . ?
C56 C57 C58 C59 -179.1(4) . . . . ?
C57 C58 C59 C60 0.2(6) . . . . ?
C58 C59 C60 C61 -0.5(6) . . . . ?
C59 C60 C61 C62 0.3(6) . . . . ?
C58 C57 C62 C61 -0.4(5) . . . . ?
C56 C57 C62 C61 178.9(3) . . . . ?
C58 C57 C62 C63 -179.2(3) . . . . ?
C56 C57 C62 C63 0.1(5) . . . . ?
C60 C61 C62 C57 0.2(5) . . . . ?
C60 C61 C62 C63 179.0(3) . . . . ?
O5 C54 C63 C62 -179.0(3) . . . . ?
C55 C54 C63 C62 0.2(5) . . . . ?
O5 C54 C63 C64 -5.3(5) . . . . ?
C55 C54 C63 C64 173.9(3) . . . . ?
C57 C62 C63 C54 0.2(5) . . . . ?
C61 C62 C63 C54 -178.6(3) . . . . ?
C57 C62 C63 C64 -173.7(3) . . . . ?
C61 C62 C63 C64 7.5(5) . . . . ?
C54 C63 C64 N5 56.0(6) . . . . ?
C62 C63 C64 N5 -130.3(4) . . . . ?
C63 C64 N5 N6 2.5(6) . . . . ?
C64 N5 N6 C65 176.7(3) . . . . ?
N5 N6 C65 O6 1.5(5) . . . . ?
N5 N6 C65 C66 -177.3(3) . . . . ?
O6 C65 C66 C67 18.5(5) . . . . ?
N6 C65 C66 C67 -162.7(3) . . . . ?
C65 C66 C67 C68 65.4(4) . . . . ?
C66 C67 C68 C69 176.5(3) . . . . ?
C67 C68 C69 C70 173.5(3) . . . . ?
C68 C69 C70 C71 -177.5(3) . . . . ?
C69 C70 C71 C72 180.0(3) . . . . ?
C78 O7 C73 C74 -162.7(3) . . . . ?
O7 C73 C74 C75 171.0(3) . . . . ?
C73 C74 C75 C76 -172.1(3) . . . . ?
C74 C75 C76 C77 -179.8(3) . . . . ?
C73 O7 C78 C87 168.2(3) . . . . ?
C73 O7 C78 C79 -14.1(5) . . . . ?
O7 C78 C79 C80 -177.8(3) . . . . ?
C87 C78 C79 C80 -0.1(5) . . . . ?
C78 C79 C80 C81 -0.3(5) . . . . ?
C79 C80 C81 C82 -179.2(3) . . . . ?
C79 C80 C81 C86 0.4(5) . . . . ?
C80 C81 C82 C83 179.3(3) . . . . ?
C86 C81 C82 C83 -0.3(5) . . . . ?
C81 C82 C83 C84 0.2(6) . . . . ?
C82 C83 C84 C85 0.2(6) . . . . ?
C83 C84 C85 C86 -0.6(5) . . . . ?
C84 C85 C86 C81 0.5(5) . . . . ?
C84 C85 C86 C87 -179.0(3) . . . . ?
C80 C81 C86 C85 -179.7(3) . . . . ?
C82 C81 C86 C85 -0.1(5) . . . . ?
C80 C81 C86 C87 -0.1(5) . . . . ?
C82 C81 C86 C87 179.5(3) . . . . ?
O7 C78 C87 C86 178.2(3) . . . . ?
C79 C78 C87 C86 0.4(5) . . . . ?
O7 C78 C87 C88 4.4(5) . . . . ?
C79 C78 C87 C88 -173.4(3) . . . . ?
C85 C86 C87 C78 179.3(3) . . . . ?
C81 C86 C87 C78 -0.3(5) . . . . ?
C85 C86 C87 C88 -6.7(5) . . . . ?
C81 C86 C87 C88 173.7(3) . . . . ?
C78 C87 C88 N7 -57.2(6) . . . . ?
C86 C87 C88 N7 128.9(4) . . . . ?
C87 C88 N7 N8 -1.9(6) . . . . ?
C88 N7 N8 C89 -176.0(3) . . . . ?
N7 N8 C89 O8 -2.1(5) . . . . ?
N7 N8 C89 C90 177.3(3) . . . . ?
O8 C89 C90 C91 -14.1(5) . . . . ?
N8 C89 C90 C91 166.4(3) . . . . ?
C89 C90 C91 C92 -65.2(4) . . . . ?
C90 C91 C92 C93 -179.1(3) . . . . ?
C91 C92 C93 C94 -176.6(3) . . . . ?
C92 C93 C94 C95 179.4(3) . . . . ?
C93 C94 C95 C96 179.4(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1 O4 0.99 2.35 3.155(4) 137.8 . yes
N2 H19 N3 0.94(5) 2.37(5) 3.110(4) 135(4) . yes
C18 H21 O4 0.99 2.46 3.396(5) 158.6 . yes
C25 H36 O2 0.99 2.46 3.158(5) 126.9 1_455 yes
N4 H53 N1 0.91(5) 2.35(4) 3.090(4) 139(4) 1_455 yes
C42 H54 O2 0.99 2.52 3.337(5) 140.2 1_455 yes
C49 H69 O8 0.99 2.45 3.155(5) 128.2 . yes
N6 H87 O5 0.87(5) 2.39(5) 2.826(4) 112(4) . yes
N6 H87 N7 0.87(5) 2.42(5) 3.131(4) 139(4) . yes
C66 H89 O8 0.99 2.47 3.369(5) 150.7 . yes
C73 H104 O6 0.99 2.48 3.186(4) 127.5 1_655 yes
N8 H121 N5 0.92(6) 2.34(5) 3.125(4) 144(5) 1_655 yes
C90 H122 O6 0.99 2.51 3.370(5) 145.3 1_655 yes

_refine_diff_density_max         0.796
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.100



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
