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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1a
_database_code_depnum_ccdc_archive 'CCDC 2267699'
loop_
_audit_author_name
_audit_author_address
'Masatoshi Kawahata'
;Showa Pharmaceutical University
Japan
;
_audit_update_record             
;
2023-06-06 deposited with the CCDC.	2023-10-23 downloaded from the CCDC.
;

## start vrf ##
_vrf_PLAT029_1a                  
;
PROBLEM:_diffrn_measured_fraction_theta_full value Low . 0.957
RESPONSE:This is due to its low crystallinity. Crystallization 
and diffraction experiments were repeated, but this data was the best.
;
## end vrf ##

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H28 N2 O7'
_chemical_formula_weight         468.49

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                   6.9004(7)
_cell_length_b                   10.5029(11)
_cell_length_c                   15.8453(17)
_cell_angle_alpha                95.066(4)
_cell_angle_beta                 92.516(4)
_cell_angle_gamma                100.761(3)
_cell_volume                     1121.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9913
_cell_measurement_theta_min      4.31
_cell_measurement_theta_max      79.29

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.845
_shelx_estimated_absorpt_T_min   0.920
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8532
_exptl_absorpt_correction_T_max  0.9424
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            16169
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.805
_diffrn_reflns_theta_max         80.080
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.904
_diffrn_measured_fraction_theta_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_point_group_measured_fraction_full 0.957
_reflns_number_total             4439
_reflns_number_gt                3983
_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       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_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)+(0.0577P)²+0.3598P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4439
_refine_ls_number_parameters     315
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.1075
_refine_ls_wR_factor_gt          0.1040
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.18788(18) 0.29853(11) 0.85452(8) 0.0188(2) Uani 1 1 d . . . . .
C2 C 0.34425(17) 0.32607(11) 0.78775(7) 0.0179(2) Uani 1 1 d . . . . .
H2A H 0.478143 0.334802 0.815428 0.021 Uiso 1 1 calc R U . . .
H2B H 0.324447 0.251789 0.743196 0.021 Uiso 1 1 calc R U . . .
C3 C 0.32848(18) 0.45241(11) 0.74647(8) 0.0183(2) Uani 1 1 d . . . . .
C4 C 0.11708(18) 0.44177(11) 0.70691(8) 0.0211(3) Uani 1 1 d . . . . .
H4A H 0.106679 0.523095 0.681349 0.025 Uiso 1 1 calc R U . . .
H4B H 0.088817 0.368961 0.661271 0.025 Uiso 1 1 calc R U . . .
C5 C -0.03523(19) 0.41844(12) 0.77434(9) 0.0240(3) Uani 1 1 d . . . . .
H5 H -0.170896 0.411158 0.747142 0.029 Uiso 1 1 calc R U . . .
C6 C -0.02139(18) 0.29197(11) 0.81351(8) 0.0218(3) Uani 1 1 d . . . . .
H6A H -0.052572 0.217715 0.768933 0.026 Uiso 1 1 calc R U . . .
H6B H -0.119584 0.277422 0.857082 0.026 Uiso 1 1 calc R U . . .
C7 C 0.2274(2) 0.41465(11) 0.92367(8) 0.0234(3) Uani 1 1 d . . . . .
H7A H 0.130157 0.399580 0.967562 0.028 Uiso 1 1 calc R U . . .
H7B H 0.361177 0.422336 0.951290 0.028 Uiso 1 1 calc R U . . .
C8 C 0.2119(2) 0.54150(11) 0.88474(8) 0.0249(3) Uani 1 1 d . . . . .
H8 H 0.239237 0.615572 0.930489 0.030 Uiso 1 1 calc R U . . .
C9 C 0.36472(19) 0.56602(11) 0.81750(8) 0.0217(3) Uani 1 1 d . . . . .
H9A H 0.499404 0.575178 0.844461 0.026 Uiso 1 1 calc R U . . .
H9B H 0.355378 0.648216 0.792841 0.026 Uiso 1 1 calc R U . . .
C10 C 0.0041(2) 0.53228(12) 0.84394(9) 0.0274(3) Uani 1 1 d . . . . .
H10A H -0.094847 0.517929 0.887234 0.033 Uiso 1 1 calc R U . . .
H10B H -0.006094 0.614351 0.819297 0.033 Uiso 1 1 calc R U . . .
C11 C 0.20247(17) 0.17012(11) 0.89089(8) 0.0188(2) Uani 1 1 d . . . . .
C12 C 0.16284(17) 0.04925(11) 0.84015(8) 0.0189(2) Uani 1 1 d . . . . .
C13 C 0.17336(18) -0.06768(11) 0.87444(8) 0.0208(3) Uani 1 1 d . . . . .
H13 H 0.145073 -0.147249 0.838729 0.025 Uiso 1 1 calc R U . . .
C14 C 0.22418(18) -0.06884(11) 0.95927(8) 0.0216(3) Uani 1 1 d . . . . .
H14 H 0.231253 -0.147984 0.982939 0.026 Uiso 1 1 calc R U . . .
C15 C 0.26465(17) 0.04930(11) 1.00892(8) 0.0200(3) Uani 1 1 d . . . . .
C16 C 0.25388(18) 0.16610(11) 0.97609(8) 0.0203(3) Uani 1 1 d . . . . .
H16 H 0.282249 0.244816 1.012652 0.024 Uiso 1 1 calc R U . . .
C17 C 0.47857(18) 0.47485(11) 0.67839(8) 0.0182(2) Uani 1 1 d . . . . .
C18 C 0.48018(18) 0.38184(11) 0.60812(8) 0.0195(2) Uani 1 1 d . . . . .
C19 C 0.62147(19) 0.40208(12) 0.54729(8) 0.0214(3) Uani 1 1 d . . . . .
H19 H 0.620861 0.337071 0.501561 0.026 Uiso 1 1 calc R U . . .
C20 C 0.76124(18) 0.51543(12) 0.55323(8) 0.0220(3) Uani 1 1 d . . . . .
H20 H 0.856335 0.530228 0.511847 0.026 Uiso 1 1 calc R U . . .
C21 C 0.75875(18) 0.60701(11) 0.62135(8) 0.0201(2) Uani 1 1 d . . . . .
C22 C 0.62110(18) 0.58865(11) 0.68276(8) 0.0191(2) Uani 1 1 d . . . . .
H22 H 0.624243 0.654464 0.728238 0.023 Uiso 1 1 calc R U . . .
C23 C 0.3527(2) 0.02668(13) 0.41008(9) 0.0283(3) Uani 1 1 d . . . . .
C24 C 0.1884(3) -0.0813(2) 0.42239(15) 0.0681(7) Uani 1 1 d . . . . .
H24A H 0.074938 -0.077780 0.383832 0.102 Uiso 1 1 calc R U . . .
H24B H 0.150486 -0.072991 0.481212 0.102 Uiso 1 1 calc R U . . .
H24C H 0.230944 -0.164627 0.410279 0.102 Uiso 1 1 calc R U . . .
C25 C 0.4734(4) 0.0126(2) 0.33613(12) 0.0619(6) Uani 1 1 d . . . . .
H25A H 0.388514 0.000730 0.283710 0.093 Uiso 1 1 calc R U . . .
H25B H 0.535916 -0.063394 0.339830 0.093 Uiso 1 1 calc R U . . .
H25C H 0.575700 0.090974 0.335893 0.093 Uiso 1 1 calc R U . . .
N1 N 0.31828(16) 0.05069(10) 1.09898(7) 0.0233(2) Uani 1 1 d . . . . .
N2 N 0.90964(16) 0.72455(10) 0.63090(7) 0.0232(2) Uani 1 1 d . . . . .
O1 O 0.11490(13) 0.04775(8) 0.75618(6) 0.0224(2) Uani 1 1 d . . . . .
H1 H 0.076(3) -0.0326(18) 0.7336(11) 0.034 Uiso 1 1 d . U . . .
O2 O 0.33555(15) -0.05279(9) 1.12635(6) 0.0307(2) Uani 1 1 d . . . . .
O3 O 0.34544(16) 0.15529(9) 1.14360(6) 0.0338(2) Uani 1 1 d . . . . .
O4 O 0.33946(14) 0.27205(8) 0.59984(6) 0.0239(2) Uani 1 1 d . . . . .
H4 H 0.351(3) 0.2239(18) 0.5524(12) 0.036 Uiso 1 1 d . U . . .
O5 O 1.03520(16) 0.74015(10) 0.57855(7) 0.0381(3) Uani 1 1 d . . . . .
O6 O 0.90684(15) 0.80472(9) 0.69288(6) 0.0314(2) Uani 1 1 d . . . . .
O7 O 0.39026(19) 0.12488(11) 0.45862(7) 0.0425(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C11 1.5310(16) . ?
C1 C7 1.5415(16) . ?
C1 C6 1.5443(17) . ?
C1 C2 1.5508(16) . ?
C2 C3 1.5496(16) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C17 1.5308(16) . ?
C3 C4 1.5427(17) . ?
C3 C9 1.5427(15) . ?
C4 C5 1.5346(17) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.5294(18) . ?
C5 C6 1.5318(17) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.5362(17) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C10 1.530(2) . ?
C8 C9 1.5360(17) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C16 1.3871(17) . ?
C11 C12 1.4155(16) . ?
C12 O1 1.3549(15) . ?
C12 C13 1.3988(17) . ?
C13 C14 1.3759(18) . ?
C13 H13 0.9500 . ?
C14 C15 1.3841(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.3872(17) . ?
C15 N1 1.4564(16) . ?
C16 H16 0.9500 . ?
C17 C22 1.3933(16) . ?
C17 C18 1.4168(16) . ?
C18 O4 1.3542(14) . ?
C18 C19 1.4022(17) . ?
C19 C20 1.3783(17) . ?
C19 H19 0.9500 . ?
C20 C21 1.3838(17) . ?
C20 H20 0.9500 . ?
C21 C22 1.3900(17) . ?
C21 N2 1.4505(15) . ?
C22 H22 0.9500 . ?
C23 O7 1.2104(17) . ?
C23 C24 1.479(2) . ?
C23 C25 1.480(2) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
N1 O2 1.2291(14) . ?
N1 O3 1.2313(14) . ?
N2 O5 1.2246(15) . ?
N2 O6 1.2392(14) . ?
O1 H1 0.875(18) . ?
O4 H4 0.884(19) . ?

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
C11 C1 C7 111.98(10) . . ?
C11 C1 C6 110.39(9) . . ?
C7 C1 C6 107.20(10) . . ?
C11 C1 C2 109.39(9) . . ?
C7 C1 C2 107.67(9) . . ?
C6 C1 C2 110.15(10) . . ?
C3 C2 C1 111.06(9) . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C17 C3 C4 110.15(10) . . ?
C17 C3 C9 111.48(9) . . ?
C4 C3 C9 107.54(10) . . ?
C17 C3 C2 110.18(9) . . ?
C4 C3 C2 109.60(9) . . ?
C9 C3 C2 107.83(10) . . ?
C5 C4 C3 110.75(10) . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C10 C5 C6 109.45(11) . . ?
C10 C5 C4 109.84(10) . . ?
C6 C5 C4 109.76(10) . . ?
C10 C5 H5 109.3 . . ?
C6 C5 H5 109.3 . . ?
C4 C5 H5 109.3 . . ?
C5 C6 C1 110.72(9) . . ?
C5 C6 H6A 109.5 . . ?
C1 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C8 C7 C1 110.42(10) . . ?
C8 C7 H7A 109.6 . . ?
C1 C7 H7A 109.6 . . ?
C8 C7 H7B 109.6 . . ?
C1 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C10 C8 C9 109.70(11) . . ?
C10 C8 C7 110.10(10) . . ?
C9 C8 C7 109.64(10) . . ?
C10 C8 H8 109.1 . . ?
C9 C8 H8 109.1 . . ?
C7 C8 H8 109.1 . . ?
C8 C9 C3 110.47(9) . . ?
C8 C9 H9A 109.6 . . ?
C3 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
C3 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C5 C10 C8 108.38(10) . . ?
C5 C10 H10A 110.0 . . ?
C8 C10 H10A 110.0 . . ?
C5 C10 H10B 110.0 . . ?
C8 C10 H10B 110.0 . . ?
H10A C10 H10B 108.4 . . ?
C16 C11 C12 116.30(11) . . ?
C16 C11 C1 121.48(10) . . ?
C12 C11 C1 122.22(11) . . ?
O1 C12 C13 119.55(10) . . ?
O1 C12 C11 118.77(11) . . ?
C13 C12 C11 121.68(11) . . ?
C14 C13 C12 120.79(11) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 117.68(11) . . ?
C13 C14 H14 121.2 . . ?
C15 C14 H14 121.2 . . ?
C14 C15 C16 122.30(12) . . ?
C14 C15 N1 118.76(11) . . ?
C16 C15 N1 118.93(10) . . ?
C11 C16 C15 121.25(11) . . ?
C11 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C22 C17 C18 116.64(11) . . ?
C22 C17 C3 121.27(10) . . ?
C18 C17 C3 122.09(10) . . ?
O4 C18 C19 119.95(11) . . ?
O4 C18 C17 118.48(11) . . ?
C19 C18 C17 121.56(11) . . ?
C20 C19 C18 120.60(11) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C21 117.94(11) . . ?
C19 C20 H20 121.0 . . ?
C21 C20 H20 121.0 . . ?
C20 C21 C22 122.47(11) . . ?
C20 C21 N2 118.90(11) . . ?
C22 C21 N2 118.60(11) . . ?
C21 C22 C17 120.76(11) . . ?
C21 C22 H22 119.6 . . ?
C17 C22 H22 119.6 . . ?
O7 C23 C24 121.86(17) . . ?
O7 C23 C25 119.78(16) . . ?
C24 C23 C25 118.37(17) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O2 N1 O3 123.39(11) . . ?
O2 N1 C15 118.12(10) . . ?
O3 N1 C15 118.48(11) . . ?
O5 N2 O6 122.69(10) . . ?
O5 N2 C21 119.24(11) . . ?
O6 N2 C21 118.06(10) . . ?
C12 O1 H1 109.9(12) . . ?
C18 O4 H4 110.3(12) . . ?

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
C11 C1 C2 C3 177.56(9) . . . . ?
C7 C1 C2 C3 -60.54(13) . . . . ?
C6 C1 C2 C3 56.05(12) . . . . ?
C1 C2 C3 C17 -177.80(9) . . . . ?
C1 C2 C3 C4 -56.44(12) . . . . ?
C1 C2 C3 C9 60.34(12) . . . . ?
C17 C3 C4 C5 179.66(9) . . . . ?
C9 C3 C4 C5 -58.67(12) . . . . ?
C2 C3 C4 C5 58.29(12) . . . . ?
C3 C4 C5 C10 60.64(13) . . . . ?
C3 C4 C5 C6 -59.75(13) . . . . ?
C10 C5 C6 C1 -61.62(13) . . . . ?
C4 C5 C6 C1 59.00(13) . . . . ?
C11 C1 C6 C5 -178.12(10) . . . . ?
C7 C1 C6 C5 59.67(12) . . . . ?
C2 C1 C6 C5 -57.21(12) . . . . ?
C11 C1 C7 C8 179.89(10) . . . . ?
C6 C1 C7 C8 -58.90(12) . . . . ?
C2 C1 C7 C8 59.60(13) . . . . ?
C1 C7 C8 C10 60.77(13) . . . . ?
C1 C7 C8 C9 -60.01(14) . . . . ?
C10 C8 C9 C3 -61.28(13) . . . . ?
C7 C8 C9 C3 59.74(14) . . . . ?
C17 C3 C9 C8 179.76(10) . . . . ?
C4 C3 C9 C8 58.93(13) . . . . ?
C2 C3 C9 C8 -59.17(13) . . . . ?
C6 C5 C10 C8 60.32(13) . . . . ?
C4 C5 C10 C8 -60.26(13) . . . . ?
C9 C8 C10 C5 60.61(12) . . . . ?
C7 C8 C10 C5 -60.14(13) . . . . ?
C7 C1 C11 C16 -2.44(16) . . . . ?
C6 C1 C11 C16 -121.79(12) . . . . ?
C2 C1 C11 C16 116.85(12) . . . . ?
C7 C1 C11 C12 176.97(11) . . . . ?
C6 C1 C11 C12 57.61(14) . . . . ?
C2 C1 C11 C12 -63.75(14) . . . . ?
C16 C11 C12 O1 -178.99(10) . . . . ?
C1 C11 C12 O1 1.57(17) . . . . ?
C16 C11 C12 C13 0.56(17) . . . . ?
C1 C11 C12 C13 -178.87(11) . . . . ?
O1 C12 C13 C14 179.16(11) . . . . ?
C11 C12 C13 C14 -0.39(18) . . . . ?
C12 C13 C14 C15 -0.15(18) . . . . ?
C13 C14 C15 C16 0.52(18) . . . . ?
C13 C14 C15 N1 179.83(11) . . . . ?
C12 C11 C16 C15 -0.20(17) . . . . ?
C1 C11 C16 C15 179.24(11) . . . . ?
C14 C15 C16 C11 -0.35(18) . . . . ?
N1 C15 C16 C11 -179.66(11) . . . . ?
C4 C3 C17 C22 117.00(12) . . . . ?
C9 C3 C17 C22 -2.29(16) . . . . ?
C2 C3 C17 C22 -121.97(12) . . . . ?
C4 C3 C17 C18 -63.02(14) . . . . ?
C9 C3 C17 C18 177.69(11) . . . . ?
C2 C3 C17 C18 58.01(15) . . . . ?
C22 C17 C18 O4 -177.58(11) . . . . ?
C3 C17 C18 O4 2.44(18) . . . . ?
C22 C17 C18 C19 1.59(18) . . . . ?
C3 C17 C18 C19 -178.39(11) . . . . ?
O4 C18 C19 C20 177.67(11) . . . . ?
C17 C18 C19 C20 -1.49(19) . . . . ?
C18 C19 C20 C21 0.80(19) . . . . ?
C19 C20 C21 C22 -0.31(19) . . . . ?
C19 C20 C21 N2 177.38(11) . . . . ?
C20 C21 C22 C17 0.48(19) . . . . ?
N2 C21 C22 C17 -177.22(11) . . . . ?
C18 C17 C22 C21 -1.08(18) . . . . ?
C3 C17 C22 C21 178.90(11) . . . . ?
C14 C15 N1 O2 3.76(17) . . . . ?
C16 C15 N1 O2 -176.90(11) . . . . ?
C14 C15 N1 O3 -176.78(11) . . . . ?
C16 C15 N1 O3 2.56(17) . . . . ?
C20 C21 N2 O5 0.14(18) . . . . ?
C22 C21 N2 O5 177.92(12) . . . . ?
C20 C21 N2 O6 -179.04(11) . . . . ?
C22 C21 N2 O6 -1.26(17) . . . . ?

_refine_diff_density_max         0.323
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_1c
_database_code_depnum_ccdc_archive 'CCDC 2267701'
loop_
_audit_author_name
_audit_author_address
'Masatoshi Kawahata'
;Showa Pharmaceutical University
Japan
;
_audit_update_record             
;
2023-06-06 deposited with the CCDC.	2023-10-23 downloaded from the CCDC.
;

## start vrf ##
_vrf_PLAT029_1c                  
;
PROBLEM:_diffrn_measured_fraction_theta_full value Low . 0.947
RESPONSE:This is due to its low crystallinity. Crystallization 
and diffraction experiments were repeated, but this data was the best.
;
## end vrf ##

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H28 N2 O8'
_chemical_formula_weight         484.49

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                   7.0715(10)
_cell_length_b                   10.4603(14)
_cell_length_c                   15.710(2)
_cell_angle_alpha                95.120(4)
_cell_angle_beta                 94.102(5)
_cell_angle_gamma                99.743(4)
_cell_volume                     1136.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9876
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      79.63

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.888
_shelx_estimated_absorpt_T_min   0.901
_shelx_estimated_absorpt_T_max   0.916
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7546
_exptl_absorpt_correction_T_max  0.9288
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            14281
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.311
_diffrn_reflns_theta_max         79.614
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.896
_diffrn_measured_fraction_theta_full 0.947
_diffrn_reflns_Laue_measured_fraction_max 0.896
_diffrn_reflns_Laue_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.896
_diffrn_reflns_point_group_measured_fraction_full 0.947
_reflns_number_total             4426
_reflns_number_gt                3956
_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       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_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)+(0.0663P)²+0.5634P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4426
_refine_ls_number_parameters     372
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1389
_refine_ls_wR_factor_gt          0.1347
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_restrained_S_all      1.134
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1917(2) 0.29475(14) 0.85634(9) 0.0214(3) Uani 1 1 d . . . . .
C2 C 0.3420(2) 0.31854(14) 0.78966(9) 0.0201(3) Uani 1 1 d . . . . .
H2A H 0.318105 0.244507 0.744096 0.024 Uiso 1 1 calc R U . . .
H2B H 0.472809 0.322960 0.818099 0.024 Uiso 1 1 calc R U . . .
C3 C 0.3316(2) 0.44721(14) 0.74865(9) 0.0208(3) Uani 1 1 d . . . . .
C4 C 0.1262(2) 0.44325(15) 0.70717(10) 0.0248(3) Uani 1 1 d . . . . .
H4A H 0.095394 0.371526 0.660076 0.030 Uiso 1 1 calc R U . . .
H4B H 0.119043 0.526251 0.682403 0.030 Uiso 1 1 calc R U . . .
C5 C -0.0218(2) 0.42223(16) 0.77425(11) 0.0285(4) Uani 1 1 d . . . . .
H5 H -0.154077 0.418678 0.745903 0.034 Uiso 1 1 calc R U . . .
C6 C -0.0124(2) 0.29402(15) 0.81338(10) 0.0250(3) Uani 1 1 d . . . . .
H6A H -0.046160 0.220122 0.767866 0.030 Uiso 1 1 calc R U . . .
H6B H -0.107461 0.281865 0.856583 0.030 Uiso 1 1 calc R U . . .
C7 C 0.2361(3) 0.41053(15) 0.92675(10) 0.0278(4) Uani 1 1 d . . . . .
H7A H 0.142721 0.397733 0.970612 0.033 Uiso 1 1 calc R U . . .
H7B H 0.366851 0.414826 0.955172 0.033 Uiso 1 1 calc R U . . .
C8 C 0.2239(3) 0.53858(16) 0.88800(11) 0.0311(4) Uani 1 1 d . . . . .
H8 H 0.253665 0.612329 0.934715 0.037 Uiso 1 1 calc R U . . .
C9 C 0.3723(2) 0.56011(15) 0.82117(10) 0.0262(3) Uani 1 1 d . . . . .
H9A H 0.365833 0.643515 0.796826 0.031 Uiso 1 1 calc R U . . .
H9B H 0.503636 0.565452 0.849279 0.031 Uiso 1 1 calc R U . . .
C10 C 0.0215(3) 0.53527(17) 0.84531(12) 0.0346(4) Uani 1 1 d . . . . .
H10A H -0.074271 0.523147 0.888187 0.041 Uiso 1 1 calc R U . . .
H10B H 0.014471 0.618546 0.820901 0.041 Uiso 1 1 calc R U . . .
C11 C 0.2014(2) 0.16510(14) 0.89334(9) 0.0214(3) Uani 1 1 d . . . . .
C12 C 0.1523(2) 0.04357(15) 0.84266(10) 0.0218(3) Uani 1 1 d . . . . .
C13 C 0.1605(2) -0.07351(15) 0.87778(10) 0.0254(3) Uani 1 1 d . . . . .
H13 H 0.124865 -0.153559 0.842158 0.030 Uiso 1 1 calc R U . . .
C14 C 0.2195(2) -0.07519(15) 0.96352(11) 0.0256(3) Uani 1 1 d . . . . .
H14 H 0.226537 -0.154787 0.987327 0.031 Uiso 1 1 calc R U . . .
C15 C 0.2674(2) 0.04277(15) 1.01291(9) 0.0232(3) Uani 1 1 d . . . . .
C16 C 0.2593(2) 0.16029(15) 0.97934(10) 0.0229(3) Uani 1 1 d . . . . .
H16 H 0.294164 0.239374 1.016004 0.027 Uiso 1 1 calc R U . . .
C17 C 0.4764(2) 0.46717(14) 0.68062(9) 0.0201(3) Uani 1 1 d . . . . .
C18 C 0.4764(2) 0.37347(15) 0.60981(10) 0.0219(3) Uani 1 1 d . . . . .
C19 C 0.6140(2) 0.39082(16) 0.54977(10) 0.0254(3) Uani 1 1 d . . . . .
H19 H 0.612844 0.324572 0.504150 0.031 Uiso 1 1 calc R U . . .
C20 C 0.7501(2) 0.50242(16) 0.55624(10) 0.0264(3) Uani 1 1 d . . . . .
H20 H 0.842903 0.514841 0.515547 0.032 Uiso 1 1 calc R U . . .
C21 C 0.7478(2) 0.59602(15) 0.62372(10) 0.0225(3) Uani 1 1 d . . . . .
C22 C 0.6153(2) 0.57953(15) 0.68509(10) 0.0223(3) Uani 1 1 d . . . . .
H22 H 0.619766 0.646208 0.730778 0.027 Uiso 1 1 calc R U . . .
N1 N 0.3294(2) 0.04420(14) 1.10388(9) 0.0278(3) Uani 1 1 d . . . . .
N2 N 0.8931(2) 0.71324(14) 0.63321(9) 0.0275(3) Uani 1 1 d . . . . .
O1 O 0.09648(17) 0.04244(11) 0.75807(7) 0.0260(3) Uani 1 1 d . . . . .
H1 H 0.049(3) -0.040(2) 0.7378(14) 0.039 Uiso 1 1 d . U . . .
O2 O 0.35019(19) -0.05886(13) 1.13171(8) 0.0371(3) Uani 1 1 d . . . . .
O3 O 0.3587(2) 0.14956(13) 1.14866(8) 0.0416(3) Uani 1 1 d . . . . .
O4 O 0.33813(16) 0.26556(11) 0.60005(7) 0.0260(3) Uani 1 1 d . . . . .
H4 H 0.354(3) 0.219(2) 0.5530(15) 0.039 Uiso 1 1 d . U . . .
O5 O 1.01546(19) 0.72583(13) 0.58119(9) 0.0404(3) Uani 1 1 d . . . . .
O6 O 0.88960(19) 0.79573(12) 0.69428(8) 0.0363(3) Uani 1 1 d . . . . .
C23 C 0.3981(5) 0.0377(3) 0.39726(16) 0.0248(9) Uani 0.699(9) 1 d . . P A 1
C24 C 0.5600(14) 0.0643(9) 0.3411(5) 0.0455(18) Uani 0.699(9) 1 d . . P A 1
H24A H 0.508406 0.079078 0.283915 0.068 Uiso 0.699(9) 1 calc R U P A 1
H24B H 0.626247 -0.010793 0.336321 0.068 Uiso 0.699(9) 1 calc R U P A 1
H24C H 0.651241 0.141879 0.366233 0.068 Uiso 0.699(9) 1 calc R U P A 1
C25 C 0.1262(15) -0.1116(9) 0.4226(5) 0.066(2) Uani 0.699(9) 1 d . . P A 1
H25A H 0.020978 -0.067057 0.404763 0.099 Uiso 0.699(9) 1 calc R U P A 1
H25B H 0.165847 -0.086285 0.483721 0.099 Uiso 0.699(9) 1 calc R U P A 1
H25C H 0.082394 -0.206129 0.413010 0.099 Uiso 0.699(9) 1 calc R U P A 1
O7 O 0.3793(13) 0.1072(13) 0.4602(9) 0.0360(14) Uani 0.699(9) 1 d . . P A 1
O8 O 0.2846(5) -0.0757(2) 0.37409(16) 0.0407(8) Uani 0.699(9) 1 d . . P A 1
C23B C 0.2981(15) 0.0030(8) 0.4187(5) 0.036(2) Uani 0.301(9) 1 d . U P A 2
C24B C 0.116(2) -0.0787(18) 0.4380(13) 0.045(3) Uani 0.301(9) 1 d . U P A 2
H24D H 0.065036 -0.141268 0.388099 0.068 Uiso 0.301(9) 1 calc R U P A 2
H24E H 0.021657 -0.022726 0.450983 0.068 Uiso 0.301(9) 1 calc R U P A 2
H24F H 0.141457 -0.125872 0.487492 0.068 Uiso 0.301(9) 1 calc R U P A 2
C25B C 0.538(3) 0.040(2) 0.3308(15) 0.051(4) Uani 0.301(9) 1 d . U P A 2
H25D H 0.578154 0.003984 0.276722 0.076 Uiso 0.301(9) 1 calc R U P A 2
H25E H 0.641587 0.046344 0.376464 0.076 Uiso 0.301(9) 1 calc R U P A 2
H25F H 0.508284 0.127259 0.324254 0.076 Uiso 0.301(9) 1 calc R U P A 2
O7B O 0.337(3) 0.111(3) 0.454(2) 0.032(3) Uani 0.301(9) 1 d . U P A 2
O8B O 0.3762(13) -0.0397(8) 0.3516(5) 0.048(2) Uani 0.301(9) 1 d . U P A 2


_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 C11 1.532(2) . ?
C1 C7 1.540(2) . ?
C1 C6 1.548(2) . ?
C1 C2 1.551(2) . ?
C2 C3 1.554(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C17 1.536(2) . ?
C3 C9 1.541(2) . ?
C3 C4 1.541(2) . ?
C4 C5 1.541(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.527(2) . ?
C5 C6 1.534(2) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.533(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C10 1.530(3) . ?
C8 C9 1.541(2) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C16 1.391(2) . ?
C11 C12 1.415(2) . ?
C12 O1 1.3572(18) . ?
C12 C13 1.396(2) . ?
C13 C14 1.384(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.375(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.389(2) . ?
C15 N1 1.4625(19) . ?
C16 H16 0.9500 . ?
C17 C22 1.391(2) . ?
C17 C18 1.416(2) . ?
C18 O4 1.3521(19) . ?
C18 C19 1.404(2) . ?
C19 C20 1.373(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.380(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.394(2) . ?
C21 N2 1.449(2) . ?
C22 H22 0.9500 . ?
N1 O2 1.2262(19) . ?
N1 O3 1.2312(19) . ?
N2 O5 1.2312(19) . ?
N2 O6 1.2363(19) . ?
O1 H1 0.89(2) . ?
O4 H4 0.87(2) . ?
C23 O7 1.203(14) . ?
C23 O8 1.321(5) . ?
C23 C24 1.499(10) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 O8 1.417(11) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C23B O7B 1.19(3) . ?
C23B O8B 1.303(15) . ?
C23B C24B 1.49(2) . ?
C24B H24D 0.9800 . ?
C24B H24E 0.9800 . ?
C24B H24F 0.9800 . ?
C25B O8B 1.37(3) . ?
C25B H25D 0.9800 . ?
C25B H25E 0.9800 . ?
C25B H25F 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
C11 C1 C7 111.57(12) . . ?
C11 C1 C6 110.49(12) . . ?
C7 C1 C6 107.32(12) . . ?
C11 C1 C2 109.96(12) . . ?
C7 C1 C2 107.71(12) . . ?
C6 C1 C2 109.71(12) . . ?
C1 C2 C3 111.32(11) . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C17 C3 C9 111.34(12) . . ?
C17 C3 C4 109.66(12) . . ?
C9 C3 C4 107.47(12) . . ?
C17 C3 C2 110.74(11) . . ?
C9 C3 C2 107.85(12) . . ?
C4 C3 C2 109.70(12) . . ?
C3 C4 C5 110.52(13) . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C10 C5 C6 109.27(14) . . ?
C10 C5 C4 109.55(14) . . ?
C6 C5 C4 110.23(12) . . ?
C10 C5 H5 109.3 . . ?
C6 C5 H5 109.3 . . ?
C4 C5 H5 109.3 . . ?
C5 C6 C1 110.77(13) . . ?
C5 C6 H6A 109.5 . . ?
C1 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C8 C7 C1 110.39(13) . . ?
C8 C7 H7A 109.6 . . ?
C1 C7 H7A 109.6 . . ?
C8 C7 H7B 109.6 . . ?
C1 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C10 C8 C7 110.49(15) . . ?
C10 C8 C9 109.63(14) . . ?
C7 C8 C9 109.61(13) . . ?
C10 C8 H8 109.0 . . ?
C7 C8 H8 109.0 . . ?
C9 C8 H8 109.0 . . ?
C3 C9 C8 110.33(13) . . ?
C3 C9 H9A 109.6 . . ?
C8 C9 H9A 109.6 . . ?
C3 C9 H9B 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C5 C10 C8 108.39(13) . . ?
C5 C10 H10A 110.0 . . ?
C8 C10 H10A 110.0 . . ?
C5 C10 H10B 110.0 . . ?
C8 C10 H10B 110.0 . . ?
H10A C10 H10B 108.4 . . ?
C16 C11 C12 115.98(14) . . ?
C16 C11 C1 121.65(13) . . ?
C12 C11 C1 122.37(13) . . ?
O1 C12 C13 119.99(13) . . ?
O1 C12 C11 118.55(13) . . ?
C13 C12 C11 121.47(14) . . ?
C14 C13 C12 121.24(14) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C15 C14 C13 117.42(14) . . ?
C15 C14 H14 121.3 . . ?
C13 C14 H14 121.3 . . ?
C14 C15 C16 122.25(14) . . ?
C14 C15 N1 118.73(14) . . ?
C16 C15 N1 119.02(14) . . ?
C15 C16 C11 121.64(14) . . ?
C15 C16 H16 119.2 . . ?
C11 C16 H16 119.2 . . ?
C22 C17 C18 116.10(14) . . ?
C22 C17 C3 121.56(13) . . ?
C18 C17 C3 122.34(13) . . ?
O4 C18 C19 119.81(13) . . ?
O4 C18 C17 118.44(13) . . ?
C19 C18 C17 121.75(14) . . ?
C20 C19 C18 120.74(14) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C20 C21 117.92(14) . . ?
C19 C20 H20 121.0 . . ?
C21 C20 H20 121.0 . . ?
C20 C21 C22 122.27(14) . . ?
C20 C21 N2 118.97(14) . . ?
C22 C21 N2 118.71(14) . . ?
C17 C22 C21 121.17(14) . . ?
C17 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
O2 N1 O3 123.30(14) . . ?
O2 N1 C15 118.69(13) . . ?
O3 N1 C15 118.01(14) . . ?
O5 N2 O6 122.90(14) . . ?
O5 N2 C21 118.98(14) . . ?
O6 N2 C21 118.11(14) . . ?
C12 O1 H1 107.6(15) . . ?
C18 O4 H4 107.6(15) . . ?
O7 C23 O8 122.8(8) . . ?
O7 C23 C24 124.2(7) . . ?
O8 C23 C24 112.7(4) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O8 C25 H25A 109.5 . . ?
O8 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O8 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C23 O8 C25 117.8(5) . . ?
O7B C23B O8B 125.3(18) . . ?
O7B C23B C24B 117.1(16) . . ?
O8B C23B C24B 115.8(10) . . ?
C23B C24B H24D 109.5 . . ?
C23B C24B H24E 109.5 . . ?
H24D C24B H24E 109.5 . . ?
C23B C24B H24F 109.5 . . ?
H24D C24B H24F 109.5 . . ?
H24E C24B H24F 109.5 . . ?
O8B C25B H25D 109.5 . . ?
O8B C25B H25E 109.5 . . ?
H25D C25B H25E 109.5 . . ?
O8B C25B H25F 109.5 . . ?
H25D C25B H25F 109.5 . . ?
H25E C25B H25F 109.5 . . ?
C23B O8B C25B 115.6(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 C1 C2 C3 178.17(11) . . . . ?
C7 C1 C2 C3 -60.06(15) . . . . ?
C6 C1 C2 C3 56.46(15) . . . . ?
C1 C2 C3 C17 -178.10(11) . . . . ?
C1 C2 C3 C9 59.85(15) . . . . ?
C1 C2 C3 C4 -56.92(15) . . . . ?
C17 C3 C4 C5 179.57(12) . . . . ?
C9 C3 C4 C5 -59.26(16) . . . . ?
C2 C3 C4 C5 57.75(16) . . . . ?
C3 C4 C5 C10 61.14(16) . . . . ?
C3 C4 C5 C6 -59.13(17) . . . . ?
C10 C5 C6 C1 -61.65(16) . . . . ?
C4 C5 C6 C1 58.79(17) . . . . ?
C11 C1 C6 C5 -178.60(12) . . . . ?
C7 C1 C6 C5 59.55(16) . . . . ?
C2 C1 C6 C5 -57.21(16) . . . . ?
C11 C1 C7 C8 -179.59(13) . . . . ?
C6 C1 C7 C8 -58.42(17) . . . . ?
C2 C1 C7 C8 59.65(17) . . . . ?
C1 C7 C8 C10 60.42(17) . . . . ?
C1 C7 C8 C9 -60.50(18) . . . . ?
C17 C3 C9 C8 179.38(12) . . . . ?
C4 C3 C9 C8 59.27(16) . . . . ?
C2 C3 C9 C8 -58.94(16) . . . . ?
C10 C8 C9 C3 -61.29(16) . . . . ?
C7 C8 C9 C3 60.15(18) . . . . ?
C6 C5 C10 C8 60.29(17) . . . . ?
C4 C5 C10 C8 -60.56(17) . . . . ?
C7 C8 C10 C5 -60.16(17) . . . . ?
C9 C8 C10 C5 60.75(17) . . . . ?
C7 C1 C11 C16 -4.8(2) . . . . ?
C6 C1 C11 C16 -124.08(15) . . . . ?
C2 C1 C11 C16 114.68(15) . . . . ?
C7 C1 C11 C12 175.20(14) . . . . ?
C6 C1 C11 C12 55.89(18) . . . . ?
C2 C1 C11 C12 -65.35(18) . . . . ?
C16 C11 C12 O1 -179.38(13) . . . . ?
C1 C11 C12 O1 0.7(2) . . . . ?
C16 C11 C12 C13 0.5(2) . . . . ?
C1 C11 C12 C13 -179.43(14) . . . . ?
O1 C12 C13 C14 179.07(14) . . . . ?
C11 C12 C13 C14 -0.9(2) . . . . ?
C12 C13 C14 C15 0.8(2) . . . . ?
C13 C14 C15 C16 -0.4(2) . . . . ?
C13 C14 C15 N1 179.69(14) . . . . ?
C14 C15 C16 C11 0.1(2) . . . . ?
N1 C15 C16 C11 -179.96(14) . . . . ?
C12 C11 C16 C15 -0.2(2) . . . . ?
C1 C11 C16 C15 179.78(14) . . . . ?
C9 C3 C17 C22 -3.87(19) . . . . ?
C4 C3 C17 C22 114.93(15) . . . . ?
C2 C3 C17 C22 -123.86(14) . . . . ?
C9 C3 C17 C18 176.46(13) . . . . ?
C4 C3 C17 C18 -64.73(17) . . . . ?
C2 C3 C17 C18 56.47(17) . . . . ?
C22 C17 C18 O4 -176.63(13) . . . . ?
C3 C17 C18 O4 3.0(2) . . . . ?
C22 C17 C18 C19 2.6(2) . . . . ?
C3 C17 C18 C19 -177.68(13) . . . . ?
O4 C18 C19 C20 176.95(14) . . . . ?
C17 C18 C19 C20 -2.3(2) . . . . ?
C18 C19 C20 C21 0.4(2) . . . . ?
C19 C20 C21 C22 1.0(2) . . . . ?
C19 C20 C21 N2 178.44(14) . . . . ?
C18 C17 C22 C21 -1.2(2) . . . . ?
C3 C17 C22 C21 179.10(13) . . . . ?
C20 C21 C22 C17 -0.6(2) . . . . ?
N2 C21 C22 C17 -178.02(13) . . . . ?
C14 C15 N1 O2 5.3(2) . . . . ?
C16 C15 N1 O2 -174.60(14) . . . . ?
C14 C15 N1 O3 -174.93(15) . . . . ?
C16 C15 N1 O3 5.2(2) . . . . ?
C20 C21 N2 O5 -0.5(2) . . . . ?
C22 C21 N2 O5 177.01(14) . . . . ?
C20 C21 N2 O6 -179.60(14) . . . . ?
C22 C21 N2 O6 -2.1(2) . . . . ?
O7 C23 O8 C25 4.6(8) . . . . ?
C24 C23 O8 C25 179.9(7) . . . . ?
O7B C23B O8B C25B 11.8(19) . . . . ?
C24B C23B O8B C25B 176.0(15) . . . . ?

_refine_diff_density_max         0.280
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_1b
_database_code_depnum_ccdc_archive 'CCDC 2267700'
loop_
_audit_author_name
_audit_author_address
'Masatoshi Kawahata'
;Showa Pharmaceutical University
Japan
;
_audit_update_record             
;
2023-06-06 deposited with the CCDC.	2023-10-23 downloaded from the CCDC.
;

## start vrf ##
_vrf_PLAT029_1b                  
;
PROBLEM:_diffrn_measured_fraction_theta_full value Low . 0.949
RESPONSE:This is due to its low crystallinity. Crystallization 
and diffraction experiments were repeated, but this data was the best.
;
## end vrf ##

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H30 N2 O7'
_chemical_formula_weight         482.52

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                   7.0766(14)
_cell_length_b                   10.505(2)
_cell_length_c                   15.939(3)
_cell_angle_alpha                95.513(6)
_cell_angle_beta                 93.850(6)
_cell_angle_gamma                100.486(5)
_cell_volume                     1155.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9104
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      79.02

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.836
_shelx_estimated_absorpt_T_min   0.885
_shelx_estimated_absorpt_T_max   0.921
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8190
_exptl_absorpt_correction_T_max  0.9288
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            15824
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.795
_diffrn_reflns_theta_max         79.471
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measured_fraction_theta_full 0.949
_diffrn_reflns_Laue_measured_fraction_max 0.901
_diffrn_reflns_Laue_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_point_group_measured_fraction_full 0.949
_reflns_number_total             4522
_reflns_number_gt                4385
_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       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_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)+(0.0507P)²+0.4491P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4522
_refine_ls_number_parameters     372
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.1040
_refine_ls_wR_factor_gt          0.1028
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.19666(17) 0.29337(10) 0.85822(7) 0.0194(2) Uani 1 1 d . . . . .
C2 C 0.34434(16) 0.31563(10) 0.79107(7) 0.0175(2) Uani 1 1 d . . . . .
H2A H 0.316354 0.241502 0.745943 0.021 Uiso 1 1 calc R U . . .
H2B H 0.475873 0.319360 0.817829 0.021 Uiso 1 1 calc R U . . .
C3 C 0.33612(16) 0.44407(10) 0.75150(7) 0.0184(2) Uani 1 1 d . . . . .
C4 C 0.12862(17) 0.44119(11) 0.71280(8) 0.0226(2) Uani 1 1 d . . . . .
H4A H 0.122985 0.523919 0.688643 0.027 Uiso 1 1 calc R U . . .
H4B H 0.093186 0.369106 0.666478 0.027 Uiso 1 1 calc R U . . .
C5 C -0.01539(18) 0.42231(12) 0.78049(9) 0.0270(3) Uani 1 1 d . . . . .
H5 H -0.148477 0.419874 0.754148 0.032 Uiso 1 1 calc R U . . .
C6 C -0.00835(17) 0.29374(11) 0.81765(8) 0.0237(3) Uani 1 1 d . . . . .
H6A H -0.045414 0.220293 0.772315 0.028 Uiso 1 1 calc R U . . .
H6B H -0.102016 0.281656 0.860978 0.028 Uiso 1 1 calc R U . . .
C7 C 0.2477(2) 0.40890(11) 0.92797(8) 0.0259(3) Uani 1 1 d . . . . .
H7A H 0.155911 0.397059 0.972063 0.031 Uiso 1 1 calc R U . . .
H7B H 0.379013 0.412000 0.954794 0.031 Uiso 1 1 calc R U . . .
C8 C 0.38382(19) 0.55700(11) 0.82347(8) 0.0241(3) Uani 1 1 d . . . . .
H8A H 0.515918 0.561276 0.849769 0.029 Uiso 1 1 calc R U . . .
H8B H 0.379405 0.640445 0.800051 0.029 Uiso 1 1 calc R U . . .
C9 C 0.2392(2) 0.53734(11) 0.89073(8) 0.0292(3) Uani 1 1 d . . . . .
H9 H 0.273550 0.611065 0.936970 0.035 Uiso 1 1 calc R U . . .
C10 C 0.0353(2) 0.53497(12) 0.85107(9) 0.0343(3) Uani 1 1 d . . . . .
H10A H -0.058118 0.523390 0.894523 0.041 Uiso 1 1 calc R U . . .
H10B H 0.029408 0.618348 0.827803 0.041 Uiso 1 1 calc R U . . .
C11 C 0.20292(16) 0.16340(10) 0.89335(7) 0.0188(2) Uani 1 1 d . . . . .
C12 C 0.15145(16) 0.04247(11) 0.84257(7) 0.0194(2) Uani 1 1 d . . . . .
C13 C 0.15758(17) -0.07493(11) 0.87600(7) 0.0217(2) Uani 1 1 d . . . . .
H13 H 0.121432 -0.154671 0.840250 0.026 Uiso 1 1 calc R U . . .
C14 C 0.21546(17) -0.07677(11) 0.96029(7) 0.0219(2) Uani 1 1 d . . . . .
H14 H 0.220750 -0.156450 0.983116 0.026 Uiso 1 1 calc R U . . .
C15 C 0.26535(16) 0.04106(11) 1.01024(7) 0.0202(2) Uani 1 1 d . . . . .
C16 C 0.25930(17) 0.15854(11) 0.97823(7) 0.0203(2) Uani 1 1 d . . . . .
H16 H 0.294329 0.237362 1.014960 0.024 Uiso 1 1 calc R U . . .
C17 C 0.47720(16) 0.46184(10) 0.68292(7) 0.0180(2) Uani 1 1 d . . . . .
C18 C 0.46734(17) 0.36741(11) 0.61201(7) 0.0200(2) Uani 1 1 d . . . . .
C19 C 0.60037(18) 0.38358(12) 0.55075(7) 0.0235(2) Uani 1 1 d . . . . .
H19 H 0.593306 0.317346 0.505046 0.028 Uiso 1 1 calc R U . . .
C20 C 0.74052(17) 0.49360(12) 0.55585(7) 0.0242(3) Uani 1 1 d . . . . .
H20 H 0.830062 0.505026 0.514127 0.029 Uiso 1 1 calc R U . . .
C21 C 0.74741(16) 0.58774(11) 0.62391(7) 0.0210(2) Uani 1 1 d . . . . .
C22 C 0.62006(16) 0.57244(11) 0.68667(7) 0.0193(2) Uani 1 1 d . . . . .
H22 H 0.631076 0.638619 0.732713 0.023 Uiso 1 1 calc R U . . .
N1 N 0.32443(15) 0.04246(10) 1.09991(6) 0.0244(2) Uani 1 1 d . . . . .
N2 N 0.89351(15) 0.70522(10) 0.63068(6) 0.0244(2) Uani 1 1 d . . . . .
O1 O 0.09518(13) 0.04099(8) 0.75911(5) 0.02401(19) Uani 1 1 d . . . . .
H1 H 0.060(2) -0.0399(17) 0.7365(10) 0.036 Uiso 1 1 d . U . . .
O2 O 0.34759(14) -0.06057(9) 1.12594(6) 0.0322(2) Uani 1 1 d . . . . .
O3 O 0.34791(16) 0.14638(9) 1.14568(6) 0.0365(2) Uani 1 1 d . . . . .
O4 O 0.32585(13) 0.26081(8) 0.60429(5) 0.0248(2) Uani 1 1 d . . . . .
H4 H 0.336(3) 0.2154(17) 0.5584(11) 0.037 Uiso 1 1 d . U . . .
O5 O 1.00354(15) 0.71924(10) 0.57462(6) 0.0400(3) Uani 1 1 d . . . . .
O6 O 0.90170(14) 0.78658(9) 0.69317(6) 0.0313(2) Uani 1 1 d . . . . .
C23 C 0.3062(2) 0.00859(15) 0.41477(9) 0.0233(4) Uani 0.811(5) 1 d . . P A 1
C24 C 0.1409(6) -0.1002(4) 0.4260(3) 0.0527(9) Uani 0.811(5) 1 d . . P A 1
H24A H 0.027497 -0.092804 0.389260 0.079 Uiso 0.811(5) 1 calc R U P A 1
H24B H 0.110204 -0.093806 0.485089 0.079 Uiso 0.811(5) 1 calc R U P A 1
H24C H 0.177823 -0.184344 0.410801 0.079 Uiso 0.811(5) 1 calc R U P A 1
C25 C 0.4074(3) -0.00540(16) 0.33567(10) 0.0281(5) Uani 0.811(5) 1 d . . P A 1
H25A H 0.312268 -0.014713 0.285952 0.034 Uiso 0.811(5) 1 calc R U P A 1
H25B H 0.462134 -0.085775 0.334106 0.034 Uiso 0.811(5) 1 calc R U P A 1
C26 C 0.5705(4) 0.1117(2) 0.3295(2) 0.0353(6) Uani 0.811(5) 1 d . . P A 1
H26A H 0.620005 0.103750 0.273656 0.053 Uiso 0.811(5) 1 calc R U P A 1
H26B H 0.675039 0.113196 0.373388 0.053 Uiso 0.811(5) 1 calc R U P A 1
H26C H 0.520284 0.192604 0.337580 0.053 Uiso 0.811(5) 1 calc R U P A 1
O7 O 0.3560(5) 0.1048(3) 0.46645(15) 0.0359(5) Uani 0.811(5) 1 d . . P A 1
C23B C 0.4129(17) 0.0577(10) 0.3895(5) 0.048(2) Uani 0.189(5) 1 d . U P A 2
C24B C 0.571(3) 0.0729(15) 0.3347(10) 0.049(2) Uani 0.189(5) 1 d . U P A 2
H24D H 0.519323 0.047148 0.275700 0.073 Uiso 0.189(5) 1 calc R U P A 2
H24E H 0.662274 0.017723 0.350446 0.073 Uiso 0.189(5) 1 calc R U P A 2
H24F H 0.637118 0.164209 0.341222 0.073 Uiso 0.189(5) 1 calc R U P A 2
C25B C 0.3088(17) -0.0659(10) 0.3604(5) 0.049(2) Uani 0.189(5) 1 d . U P A 2
H25C H 0.393432 -0.131305 0.358565 0.059 Uiso 0.189(5) 1 calc R U P A 2
H25D H 0.243627 -0.067253 0.303262 0.059 Uiso 0.189(5) 1 calc R U P A 2
C26B C 0.162(3) -0.0910(19) 0.4262(13) 0.049(2) Uani 0.189(5) 1 d . U P A 2
H26D H 0.210091 -0.141729 0.468547 0.073 Uiso 0.189(5) 1 calc R U P A 2
H26E H 0.038806 -0.139720 0.398116 0.073 Uiso 0.189(5) 1 calc R U P A 2
H26F H 0.142199 -0.007667 0.454099 0.073 Uiso 0.189(5) 1 calc R U P A 2
O7B O 0.370(3) 0.1238(17) 0.4501(9) 0.049(2) Uani 0.189(5) 1 d . U P A 2


_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 C11 1.5314(15) . ?
C1 C7 1.5385(16) . ?
C1 C6 1.5491(17) . ?
C1 C2 1.5499(15) . ?
C2 C3 1.5520(15) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C17 1.5311(15) . ?
C3 C8 1.5421(16) . ?
C3 C4 1.5479(16) . ?
C4 C5 1.5353(16) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.527(2) . ?
C5 C6 1.5335(16) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C9 1.5347(16) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.5339(16) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.531(2) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C16 1.3930(16) . ?
C11 C12 1.4129(16) . ?
C12 O1 1.3606(14) . ?
C12 C13 1.3963(16) . ?
C13 C14 1.3811(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.3801(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.3865(16) . ?
C15 N1 1.4600(15) . ?
C16 H16 0.9500 . ?
C17 C22 1.3880(16) . ?
C17 C18 1.4195(15) . ?
C18 O4 1.3493(14) . ?
C18 C19 1.4020(16) . ?
C19 C20 1.3711(18) . ?
C19 H19 0.9500 . ?
C20 C21 1.3881(17) . ?
C20 H20 0.9500 . ?
C21 C22 1.3921(16) . ?
C21 N2 1.4486(15) . ?
C22 H22 0.9500 . ?
N1 O2 1.2297(14) . ?
N1 O3 1.2314(14) . ?
N2 O5 1.2262(14) . ?
N2 O6 1.2396(14) . ?
O1 H1 0.875(18) . ?
O4 H4 0.848(18) . ?
C23 O7 1.223(3) . ?
C23 C25 1.499(2) . ?
C23 C24 1.512(4) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.542(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C23B O7B 1.223(18) . ?
C23B C25B 1.390(16) . ?
C23B C24B 1.46(2) . ?
C24B H24D 0.9800 . ?
C24B H24E 0.9800 . ?
C24B H24F 0.9800 . ?
C25B C26B 1.54(2) . ?
C25B H25C 0.9900 . ?
C25B H25D 0.9900 . ?
C26B H26D 0.9800 . ?
C26B H26E 0.9800 . ?
C26B H26F 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
C11 C1 C7 111.80(9) . . ?
C11 C1 C6 110.25(9) . . ?
C7 C1 C6 107.56(9) . . ?
C11 C1 C2 109.79(9) . . ?
C7 C1 C2 107.75(9) . . ?
C6 C1 C2 109.62(9) . . ?
C1 C2 C3 111.17(8) . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C17 C3 C8 111.64(9) . . ?
C17 C3 C4 109.74(9) . . ?
C8 C3 C4 107.54(9) . . ?
C17 C3 C2 110.47(9) . . ?
C8 C3 C2 107.74(9) . . ?
C4 C3 C2 109.64(9) . . ?
C5 C4 C3 110.54(10) . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C10 C5 C6 109.37(11) . . ?
C10 C5 C4 109.84(10) . . ?
C6 C5 C4 109.75(9) . . ?
C10 C5 H5 109.3 . . ?
C6 C5 H5 109.3 . . ?
C4 C5 H5 109.3 . . ?
C5 C6 C1 110.75(10) . . ?
C5 C6 H6A 109.5 . . ?
C1 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C9 C7 C1 110.43(10) . . ?
C9 C7 H7A 109.6 . . ?
C1 C7 H7A 109.6 . . ?
C9 C7 H7B 109.6 . . ?
C1 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C9 C8 C3 110.49(10) . . ?
C9 C8 H8A 109.6 . . ?
C3 C8 H8A 109.6 . . ?
C9 C8 H8B 109.6 . . ?
C3 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C10 C9 C8 109.81(11) . . ?
C10 C9 C7 110.00(11) . . ?
C8 C9 C7 109.64(10) . . ?
C10 C9 H9 109.1 . . ?
C8 C9 H9 109.1 . . ?
C7 C9 H9 109.1 . . ?
C5 C10 C9 108.65(10) . . ?
C5 C10 H10A 110.0 . . ?
C9 C10 H10A 110.0 . . ?
C5 C10 H10B 110.0 . . ?
C9 C10 H10B 110.0 . . ?
H10A C10 H10B 108.3 . . ?
C16 C11 C12 116.26(10) . . ?
C16 C11 C1 121.22(10) . . ?
C12 C11 C1 122.51(10) . . ?
O1 C12 C13 119.48(10) . . ?
O1 C12 C11 118.96(10) . . ?
C13 C12 C11 121.56(10) . . ?
C14 C13 C12 120.93(10) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C15 C14 C13 117.74(10) . . ?
C15 C14 H14 121.1 . . ?
C13 C14 H14 121.1 . . ?
C14 C15 C16 122.12(11) . . ?
C14 C15 N1 119.14(10) . . ?
C16 C15 N1 118.73(10) . . ?
C15 C16 C11 121.38(10) . . ?
C15 C16 H16 119.3 . . ?
C11 C16 H16 119.3 . . ?
C22 C17 C18 116.68(10) . . ?
C22 C17 C3 121.38(10) . . ?
C18 C17 C3 121.94(10) . . ?
O4 C18 C19 120.17(10) . . ?
O4 C18 C17 118.54(10) . . ?
C19 C18 C17 121.29(11) . . ?
C20 C19 C18 120.96(11) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C21 117.89(11) . . ?
C19 C20 H20 121.1 . . ?
C21 C20 H20 121.1 . . ?
C20 C21 C22 122.21(11) . . ?
C20 C21 N2 119.05(10) . . ?
C22 C21 N2 118.73(11) . . ?
C17 C22 C21 120.92(11) . . ?
C17 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
O2 N1 O3 123.33(10) . . ?
O2 N1 C15 118.19(10) . . ?
O3 N1 C15 118.48(10) . . ?
O5 N2 O6 123.15(11) . . ?
O5 N2 C21 118.54(11) . . ?
O6 N2 C21 118.32(10) . . ?
C12 O1 H1 109.0(11) . . ?
C18 O4 H4 107.7(12) . . ?
O7 C23 C25 120.6(2) . . ?
O7 C23 C24 122.7(3) . . ?
C25 C23 C24 116.8(2) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 C26 112.65(16) . . ?
C23 C25 H25A 109.1 . . ?
C26 C25 H25A 109.1 . . ?
C23 C25 H25B 109.1 . . ?
C26 C25 H25B 109.1 . . ?
H25A C25 H25B 107.8 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O7B C23B C25B 122.5(12) . . ?
O7B C23B C24B 134.6(13) . . ?
C25B C23B C24B 102.8(10) . . ?
C23B C24B H24D 109.5 . . ?
C23B C24B H24E 109.5 . . ?
H24D C24B H24E 109.5 . . ?
C23B C24B H24F 109.5 . . ?
H24D C24B H24F 109.5 . . ?
H24E C24B H24F 109.5 . . ?
C23B C25B C26B 103.0(10) . . ?
C23B C25B H25C 111.2 . . ?
C26B C25B H25C 111.2 . . ?
C23B C25B H25D 111.2 . . ?
C26B C25B H25D 111.2 . . ?
H25C C25B H25D 109.1 . . ?
C25B C26B H26D 109.5 . . ?
C25B C26B H26E 109.5 . . ?
H26D C26B H26E 109.5 . . ?
C25B C26B H26F 109.5 . . ?
H26D C26B H26F 109.5 . . ?
H26E C26B H26F 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
C11 C1 C2 C3 177.75(9) . . . . ?
C7 C1 C2 C3 -60.27(12) . . . . ?
C6 C1 C2 C3 56.50(12) . . . . ?
C1 C2 C3 C17 -177.80(9) . . . . ?
C1 C2 C3 C8 60.02(12) . . . . ?
C1 C2 C3 C4 -56.73(12) . . . . ?
C17 C3 C4 C5 179.54(9) . . . . ?
C8 C3 C4 C5 -58.84(12) . . . . ?
C2 C3 C4 C5 58.04(12) . . . . ?
C3 C4 C5 C10 60.64(12) . . . . ?
C3 C4 C5 C6 -59.63(13) . . . . ?
C10 C5 C6 C1 -61.02(12) . . . . ?
C4 C5 C6 C1 59.54(13) . . . . ?
C11 C1 C6 C5 -178.76(9) . . . . ?
C7 C1 C6 C5 59.10(12) . . . . ?
C2 C1 C6 C5 -57.79(12) . . . . ?
C11 C1 C7 C9 -179.74(10) . . . . ?
C6 C1 C7 C9 -58.57(12) . . . . ?
C2 C1 C7 C9 59.54(13) . . . . ?
C17 C3 C8 C9 179.44(9) . . . . ?
C4 C3 C8 C9 59.00(12) . . . . ?
C2 C3 C8 C9 -59.11(12) . . . . ?
C3 C8 C9 C10 -61.00(12) . . . . ?
C3 C8 C9 C7 59.97(14) . . . . ?
C1 C7 C9 C10 60.67(13) . . . . ?
C1 C7 C9 C8 -60.19(14) . . . . ?
C6 C5 C10 C9 60.38(13) . . . . ?
C4 C5 C10 C9 -60.13(13) . . . . ?
C8 C9 C10 C5 60.31(12) . . . . ?
C7 C9 C10 C5 -60.44(13) . . . . ?
C7 C1 C11 C16 -3.10(15) . . . . ?
C6 C1 C11 C16 -122.70(11) . . . . ?
C2 C1 C11 C16 116.44(11) . . . . ?
C7 C1 C11 C12 176.50(10) . . . . ?
C6 C1 C11 C12 56.90(13) . . . . ?
C2 C1 C11 C12 -63.97(14) . . . . ?
C16 C11 C12 O1 -179.98(10) . . . . ?
C1 C11 C12 O1 0.41(16) . . . . ?
C16 C11 C12 C13 -0.16(16) . . . . ?
C1 C11 C12 C13 -179.77(10) . . . . ?
O1 C12 C13 C14 179.49(10) . . . . ?
C11 C12 C13 C14 -0.32(18) . . . . ?
C12 C13 C14 C15 0.50(17) . . . . ?
C13 C14 C15 C16 -0.20(17) . . . . ?
C13 C14 C15 N1 179.10(10) . . . . ?
C14 C15 C16 C11 -0.29(18) . . . . ?
N1 C15 C16 C11 -179.59(10) . . . . ?
C12 C11 C16 C15 0.45(16) . . . . ?
C1 C11 C16 C15 -179.93(10) . . . . ?
C8 C3 C17 C22 -3.55(14) . . . . ?
C4 C3 C17 C22 115.59(11) . . . . ?
C2 C3 C17 C22 -123.41(11) . . . . ?
C8 C3 C17 C18 177.27(10) . . . . ?
C4 C3 C17 C18 -63.60(13) . . . . ?
C2 C3 C17 C18 57.41(13) . . . . ?
C22 C17 C18 O4 -177.48(10) . . . . ?
C3 C17 C18 O4 1.74(16) . . . . ?
C22 C17 C18 C19 2.31(16) . . . . ?
C3 C17 C18 C19 -178.47(10) . . . . ?
O4 C18 C19 C20 177.48(10) . . . . ?
C17 C18 C19 C20 -2.31(18) . . . . ?
C18 C19 C20 C21 0.55(17) . . . . ?
C19 C20 C21 C22 1.12(17) . . . . ?
C19 C20 C21 N2 -179.74(10) . . . . ?
C18 C17 C22 C21 -0.66(16) . . . . ?
C3 C17 C22 C21 -179.89(10) . . . . ?
C20 C21 C22 C17 -1.05(17) . . . . ?
N2 C21 C22 C17 179.80(10) . . . . ?
C14 C15 N1 O2 7.68(16) . . . . ?
C16 C15 N1 O2 -173.00(10) . . . . ?
C14 C15 N1 O3 -172.07(11) . . . . ?
C16 C15 N1 O3 7.25(16) . . . . ?
C20 C21 N2 O5 1.93(16) . . . . ?
C22 C21 N2 O5 -178.90(11) . . . . ?
C20 C21 N2 O6 -177.79(10) . . . . ?
C22 C21 N2 O6 1.38(16) . . . . ?
O7 C23 C25 C26 -0.4(3) . . . . ?
C24 C23 C25 C26 178.8(3) . . . . ?
O7B C23B C25B C26B -5.5(16) . . . . ?
C24B C23B C25B C26B 171.5(12) . . . . ?

_refine_diff_density_max         0.258
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_1d
_database_code_depnum_ccdc_archive 'CCDC 2267702'
loop_
_audit_author_name
_audit_author_address
'Masatoshi Kawahata'
;Showa Pharmaceutical University
Japan
;
_audit_update_record             
;
2023-06-06 deposited with the CCDC.	2023-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H22 N2 O6'
_chemical_formula_weight         410.41

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                   10.8801(12)
_cell_length_b                   12.8327(14)
_cell_length_c                   13.3727(14)
_cell_angle_alpha                90
_cell_angle_beta                 93.490(4)
_cell_angle_gamma                90
_cell_volume                     1863.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9910
_cell_measurement_theta_min      3.44
_cell_measurement_theta_max      79.52

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.893
_shelx_estimated_absorpt_T_min   0.842
_shelx_estimated_absorpt_T_max   0.842
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8070
_exptl_absorpt_correction_T_max  0.8769
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            22303
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.780
_diffrn_reflns_theta_max         79.134
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             3832
_reflns_number_gt                3827
_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       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_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)+(0.0353P)²+1.0597P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0088(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3832
_refine_ls_number_parameters     278
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0874
_refine_ls_wR_factor_gt          0.0874
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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 0.26541(9) 0.44330(8) 0.27114(8) 0.0122(2) Uani 1 1 d . . . . .
C2 C 0.34491(9) 0.52767(8) 0.22321(7) 0.0117(2) Uani 1 1 d . . . . .
H2A H 0.343747 0.592056 0.263918 0.014 Uiso 1 1 calc R U . . .
H2B H 0.431190 0.503122 0.223424 0.014 Uiso 1 1 calc R U . . .
C3 C 0.29764(9) 0.55261(8) 0.11448(7) 0.0118(2) Uani 1 1 d . . . . .
C4 C 0.30120(10) 0.44995(8) 0.05403(8) 0.0138(2) Uani 1 1 d . . . . .
H4A H 0.272494 0.463152 -0.016503 0.017 Uiso 1 1 calc R U . . .
H4B H 0.386880 0.423841 0.054898 0.017 Uiso 1 1 calc R U . . .
C5 C 0.21850(10) 0.36749(8) 0.09943(8) 0.0147(2) Uani 1 1 d . . . . .
H5 H 0.220336 0.302356 0.058493 0.018 Uiso 1 1 calc R U . . .
C6 C 0.26513(10) 0.34303(8) 0.20719(8) 0.0142(2) Uani 1 1 d . . . . .
H6A H 0.349562 0.314200 0.207677 0.017 Uiso 1 1 calc R U . . .
H6B H 0.211281 0.290122 0.236007 0.017 Uiso 1 1 calc R U . . .
C7 C 0.13159(9) 0.48361(9) 0.26907(8) 0.0149(2) Uani 1 1 d . . . . .
H7A H 0.078582 0.430423 0.298438 0.018 Uiso 1 1 calc R U . . .
H7B H 0.128336 0.547583 0.310196 0.018 Uiso 1 1 calc R U . . .
C8 C 0.08290(9) 0.50747(9) 0.16157(8) 0.0153(2) Uani 1 1 d . . . . .
H8 H -0.003814 0.533182 0.162178 0.018 Uiso 1 1 calc R U . . .
C9 C 0.16318(9) 0.59166(8) 0.11689(8) 0.0140(2) Uani 1 1 d . . . . .
H9A H 0.160864 0.655841 0.157808 0.017 Uiso 1 1 calc R U . . .
H9B H 0.130619 0.608561 0.048061 0.017 Uiso 1 1 calc R U . . .
C10 C 0.08590(10) 0.40808(9) 0.09802(8) 0.0172(2) Uani 1 1 d . . . . .
H10A H 0.031794 0.354466 0.125407 0.021 Uiso 1 1 calc R U . . .
H10B H 0.055443 0.423372 0.028299 0.021 Uiso 1 1 calc R U . . .
C11 C 0.31674(9) 0.42137(8) 0.37835(8) 0.0128(2) Uani 1 1 d . . . . .
C12 C 0.43668(10) 0.38083(8) 0.39973(8) 0.0139(2) Uani 1 1 d . . . . .
C13 C 0.48134(10) 0.36076(9) 0.49798(8) 0.0174(2) Uani 1 1 d . . . . .
H13 H 0.560938 0.331237 0.509983 0.021 Uiso 1 1 calc R U . . .
C14 C 0.41114(11) 0.38334(9) 0.57795(8) 0.0188(2) Uani 1 1 d . . . . .
H14 H 0.441760 0.370737 0.644906 0.023 Uiso 1 1 calc R U . . .
C15 C 0.29502(10) 0.42483(9) 0.55760(8) 0.0162(2) Uani 1 1 d . . . . .
C16 C 0.24731(10) 0.44231(8) 0.46035(8) 0.0146(2) Uani 1 1 d . . . . .
H16 H 0.166126 0.468938 0.449494 0.017 Uiso 1 1 calc R U . . .
C17 C 0.37861(9) 0.63477(8) 0.06774(8) 0.0123(2) Uani 1 1 d . . . . .
C18 C 0.35749(10) 0.66895(8) -0.03275(8) 0.0141(2) Uani 1 1 d . . . . .
C19 C 0.43515(10) 0.74146(8) -0.07512(8) 0.0150(2) Uani 1 1 d . . . . .
H19 H 0.418506 0.762750 -0.142633 0.018 Uiso 1 1 calc R U . . .
C20 C 0.53558(10) 0.78263(8) -0.02052(8) 0.0146(2) Uani 1 1 d . . . . .
H20 H 0.588843 0.831347 -0.049353 0.018 Uiso 1 1 calc R U . . .
C21 C 0.55558(9) 0.75014(8) 0.07784(8) 0.0132(2) Uani 1 1 d . . . . .
C22 C 0.47922(9) 0.67841(8) 0.12152(8) 0.0130(2) Uani 1 1 d . . . . .
H22 H 0.496192 0.658873 0.189478 0.016 Uiso 1 1 calc R U . . .
N1 N 0.22032(10) 0.45232(8) 0.64095(7) 0.0209(2) Uani 1 1 d . . . . .
N2 N 0.66241(8) 0.78766(7) 0.13707(7) 0.0148(2) Uani 1 1 d . . . . .
O1 O 0.50917(7) 0.36123(7) 0.32240(6) 0.01777(19) Uani 1 1 d . . . . .
H1 H 0.5813(16) 0.3484(13) 0.3470(12) 0.027 Uiso 1 1 d . U . . .
O2 O 0.26720(10) 0.44471(9) 0.72665(7) 0.0387(3) Uani 1 1 d . . . . .
O3 O 0.11386(8) 0.48250(7) 0.62215(7) 0.0252(2) Uani 1 1 d . . . . .
O4 O 0.25970(7) 0.62907(7) -0.08735(6) 0.01883(19) Uani 1 1 d . . . . .
H4 H 0.2547(15) 0.6525(13) -0.1462(13) 0.028 Uiso 1 1 d . U . . .
O5 O 0.74911(7) 0.82485(7) 0.09246(6) 0.01937(19) Uani 1 1 d . . . . .
O6 O 0.66416(8) 0.78046(7) 0.22899(6) 0.0235(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C11 1.5326(14) . ?
C1 C7 1.5439(14) . ?
C1 C6 1.5449(14) . ?
C1 C2 1.5488(14) . ?
C2 C3 1.5460(13) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C17 1.5315(14) . ?
C3 C4 1.5473(14) . ?
C3 C9 1.5485(14) . ?
C4 C5 1.5377(15) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.5309(14) . ?
C5 C10 1.5329(15) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.5324(15) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.5332(15) . ?
C8 C10 1.5341(15) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C16 1.3950(15) . ?
C11 C12 1.4177(15) . ?
C12 O1 1.3616(13) . ?
C12 C13 1.3967(15) . ?
C13 C14 1.3822(16) . ?
C13 H13 0.9500 . ?
C14 C15 1.3827(16) . ?
C14 H14 0.9500 . ?
C15 C16 1.3889(15) . ?
C15 N1 1.4620(14) . ?
C16 H16 0.9500 . ?
C17 C22 1.3904(14) . ?
C17 C18 1.4190(14) . ?
C18 O4 1.3537(13) . ?
C18 C19 1.3996(16) . ?
C19 C20 1.3818(15) . ?
C19 H19 0.9500 . ?
C20 C21 1.3844(15) . ?
C20 H20 0.9500 . ?
C21 C22 1.3921(15) . ?
C21 N2 1.4484(13) . ?
C22 H22 0.9500 . ?
N1 O2 1.2296(14) . ?
N1 O3 1.2326(14) . ?
N2 O6 1.2317(12) . ?
N2 O5 1.2418(12) . ?
O1 H1 0.848(17) . ?
O4 H4 0.841(17) . ?

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
C11 C1 C7 111.58(8) . . ?
C11 C1 C6 110.68(8) . . ?
C7 C1 C6 107.40(8) . . ?
C11 C1 C2 109.55(8) . . ?
C7 C1 C2 107.95(8) . . ?
C6 C1 C2 109.60(8) . . ?
C3 C2 C1 111.82(8) . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
C17 C3 C2 111.08(8) . . ?
C17 C3 C4 109.85(8) . . ?
C2 C3 C4 107.31(8) . . ?
C17 C3 C9 110.69(8) . . ?
C2 C3 C9 107.94(8) . . ?
C4 C3 C9 109.89(8) . . ?
C5 C4 C3 110.23(8) . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C6 C5 C10 109.81(9) . . ?
C6 C5 C4 110.15(8) . . ?
C10 C5 C4 109.53(9) . . ?
C6 C5 H5 109.1 . . ?
C10 C5 H5 109.1 . . ?
C4 C5 H5 109.1 . . ?
C5 C6 C1 109.86(8) . . ?
C5 C6 H6A 109.7 . . ?
C1 C6 H6A 109.7 . . ?
C5 C6 H6B 109.7 . . ?
C1 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C8 C7 C1 110.83(8) . . ?
C8 C7 H7A 109.5 . . ?
C1 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C7 C8 C9 109.50(8) . . ?
C7 C8 C10 109.62(9) . . ?
C9 C8 C10 109.77(9) . . ?
C7 C8 H8 109.3 . . ?
C9 C8 H8 109.3 . . ?
C10 C8 H8 109.3 . . ?
C8 C9 C3 109.96(8) . . ?
C8 C9 H9A 109.7 . . ?
C3 C9 H9A 109.7 . . ?
C8 C9 H9B 109.7 . . ?
C3 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C5 C10 C8 109.11(8) . . ?
C5 C10 H10A 109.9 . . ?
C8 C10 H10A 109.9 . . ?
C5 C10 H10B 109.9 . . ?
C8 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
C16 C11 C12 116.61(10) . . ?
C16 C11 C1 121.06(9) . . ?
C12 C11 C1 122.32(9) . . ?
O1 C12 C13 119.73(10) . . ?
O1 C12 C11 118.90(9) . . ?
C13 C12 C11 121.37(10) . . ?
C14 C13 C12 120.81(10) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 118.02(10) . . ?
C13 C14 H14 121.0 . . ?
C15 C14 H14 121.0 . . ?
C14 C15 C16 122.10(10) . . ?
C14 C15 N1 119.11(10) . . ?
C16 C15 N1 118.78(10) . . ?
C15 C16 C11 121.04(10) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
C22 C17 C18 116.25(10) . . ?
C22 C17 C3 121.37(9) . . ?
C18 C17 C3 122.37(9) . . ?
O4 C18 C19 120.47(9) . . ?
O4 C18 C17 118.07(10) . . ?
C19 C18 C17 121.47(10) . . ?
C20 C19 C18 121.18(10) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C19 C20 C21 117.42(10) . . ?
C19 C20 H20 121.3 . . ?
C21 C20 H20 121.3 . . ?
C20 C21 C22 122.31(10) . . ?
C20 C21 N2 119.60(9) . . ?
C22 C21 N2 118.03(9) . . ?
C17 C22 C21 121.37(9) . . ?
C17 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
O2 N1 O3 123.12(10) . . ?
O2 N1 C15 118.23(10) . . ?
O3 N1 C15 118.65(10) . . ?
O6 N2 O5 122.83(9) . . ?
O6 N2 C21 118.95(9) . . ?
O5 N2 C21 118.22(9) . . ?
C12 O1 H1 107.8(11) . . ?
C18 O4 H4 112.0(11) . . ?

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
C11 C1 C2 C3 179.71(8) . . . . ?
C7 C1 C2 C3 -58.59(11) . . . . ?
C6 C1 C2 C3 58.09(11) . . . . ?
C1 C2 C3 C17 -179.03(8) . . . . ?
C1 C2 C3 C4 -58.95(10) . . . . ?
C1 C2 C3 C9 59.44(11) . . . . ?
C17 C3 C4 C5 -179.10(8) . . . . ?
C2 C3 C4 C5 60.03(10) . . . . ?
C9 C3 C4 C5 -57.09(11) . . . . ?
C3 C4 C5 C6 -61.61(11) . . . . ?
C3 C4 C5 C10 59.27(11) . . . . ?
C10 C5 C6 C1 -61.58(11) . . . . ?
C4 C5 C6 C1 59.12(11) . . . . ?
C11 C1 C6 C5 -177.71(8) . . . . ?
C7 C1 C6 C5 60.26(11) . . . . ?
C2 C1 C6 C5 -56.77(11) . . . . ?
C11 C1 C7 C8 178.69(9) . . . . ?
C6 C1 C7 C8 -59.84(11) . . . . ?
C2 C1 C7 C8 58.27(11) . . . . ?
C1 C7 C8 C9 -60.44(11) . . . . ?
C1 C7 C8 C10 60.03(11) . . . . ?
C7 C8 C9 C3 60.81(11) . . . . ?
C10 C8 C9 C3 -59.57(11) . . . . ?
C17 C3 C9 C8 178.65(8) . . . . ?
C2 C3 C9 C8 -59.58(11) . . . . ?
C4 C3 C9 C8 57.15(11) . . . . ?
C6 C5 C10 C8 59.97(11) . . . . ?
C4 C5 C10 C8 -61.11(11) . . . . ?
C7 C8 C10 C5 -58.83(11) . . . . ?
C9 C8 C10 C5 61.48(11) . . . . ?
C7 C1 C11 C16 -2.93(14) . . . . ?
C6 C1 C11 C16 -122.48(10) . . . . ?
C2 C1 C11 C16 116.55(11) . . . . ?
C7 C1 C11 C12 178.14(10) . . . . ?
C6 C1 C11 C12 58.59(13) . . . . ?
C2 C1 C11 C12 -62.38(13) . . . . ?
C16 C11 C12 O1 -178.58(9) . . . . ?
C1 C11 C12 O1 0.40(15) . . . . ?
C16 C11 C12 C13 1.46(16) . . . . ?
C1 C11 C12 C13 -179.57(10) . . . . ?
O1 C12 C13 C14 177.77(10) . . . . ?
C11 C12 C13 C14 -2.27(17) . . . . ?
C12 C13 C14 C15 0.94(17) . . . . ?
C13 C14 C15 C16 1.13(17) . . . . ?
C13 C14 C15 N1 -178.18(10) . . . . ?
C14 C15 C16 C11 -1.93(17) . . . . ?
N1 C15 C16 C11 177.39(10) . . . . ?
C12 C11 C16 C15 0.59(16) . . . . ?
C1 C11 C16 C15 -178.40(10) . . . . ?
C2 C3 C17 C22 -0.68(13) . . . . ?
C4 C3 C17 C22 -119.25(10) . . . . ?
C9 C3 C17 C22 119.22(10) . . . . ?
C2 C3 C17 C18 177.87(9) . . . . ?
C4 C3 C17 C18 59.31(12) . . . . ?
C9 C3 C17 C18 -62.22(12) . . . . ?
C22 C17 C18 O4 -179.36(9) . . . . ?
C3 C17 C18 O4 2.01(15) . . . . ?
C22 C17 C18 C19 0.88(15) . . . . ?
C3 C17 C18 C19 -177.75(10) . . . . ?
O4 C18 C19 C20 -179.77(10) . . . . ?
C17 C18 C19 C20 -0.02(16) . . . . ?
C18 C19 C20 C21 -0.61(16) . . . . ?
C19 C20 C21 C22 0.37(16) . . . . ?
C19 C20 C21 N2 177.48(9) . . . . ?
C18 C17 C22 C21 -1.12(15) . . . . ?
C3 C17 C22 C21 177.52(9) . . . . ?
C20 C21 C22 C17 0.53(16) . . . . ?
N2 C21 C22 C17 -176.63(9) . . . . ?
C14 C15 N1 O2 5.31(16) . . . . ?
C16 C15 N1 O2 -174.03(11) . . . . ?
C14 C15 N1 O3 -175.08(10) . . . . ?
C16 C15 N1 O3 5.58(15) . . . . ?
C20 C21 N2 O6 162.02(10) . . . . ?
C22 C21 N2 O6 -20.74(15) . . . . ?
C20 C21 N2 O5 -18.71(14) . . . . ?
C22 C21 N2 O5 158.52(10) . . . . ?

_refine_diff_density_max         0.348
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_2a
_database_code_depnum_ccdc_archive 'CCDC 2267703'
loop_
_audit_author_name
_audit_author_address
'Masatoshi Kawahata'
;Showa Pharmaceutical University
Japan
;
_audit_update_record             
;
2023-06-06 deposited with the CCDC.	2023-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H22 N2 O6'
_chemical_formula_weight         410.41

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           63
_space_group_name_H-M_alt        'C m c m'
_space_group_name_Hall           '-C 2c 2'

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

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

_cell_length_a                   6.6173(6)
_cell_length_b                   13.6049(11)
_cell_length_c                   20.3294(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1830.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9043
_cell_measurement_theta_min      6.86
_cell_measurement_theta_max      78.10

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.910
_shelx_estimated_absorpt_T_min   0.915
_shelx_estimated_absorpt_T_max   0.931
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8526
_exptl_absorpt_correction_T_max  0.9424
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            11088
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         6.863
_diffrn_reflns_theta_max         78.085
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             1079
_reflns_number_gt                1028
_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       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_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)+(0.0624P)²+1.1549P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1079
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1149
_refine_ls_wR_factor_gt          0.1129
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_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 0.500000 0.64905(11) 0.68732(7) 0.0244(4) Uani 1 2 d S T P . .
C2 C 0.3101(2) 0.58290(8) 0.68846(5) 0.0289(3) Uani 1 1 d . . . . .
H2A H 0.187232 0.624390 0.688432 0.035 Uiso 1 1 calc R U . . .
H2B H 0.307462 0.541210 0.648560 0.035 Uiso 1 1 calc R U . . .
C3 C 0.3116(3) 0.51753(11) 0.750000 0.0325(4) Uani 1 2 d S T P . .
H3 H 0.188295 0.475005 0.749999 0.039 Uiso 1 2 calc R U P . .
C4 C 0.500000 0.45245(16) 0.750000 0.0373(6) Uani 1 4 d S T P . .
H4A H 0.500000 0.409815 0.789463 0.045 Uiso 0.5 2 calc R U P . .
H4B H 0.499999 0.409815 0.710537 0.045 Uiso 0.5 2 calc R U P . .
C5 C 0.500000 0.71235(15) 0.750000 0.0248(5) Uani 1 4 d S T P . .
H5A H 0.620974 0.755166 0.750000 0.030 Uiso 0.5 2 calc R U P . .
H5B H 0.379026 0.755166 0.750000 0.030 Uiso 0.5 2 calc R U P . .
C6 C 0.500000 0.71234(11) 0.62529(7) 0.0249(4) Uani 1 2 d S T P . .
C7 C 0.500000 0.66762(11) 0.56406(7) 0.0251(4) Uani 1 2 d S T P . .
H7 H 0.500000 0.597922 0.561166 0.030 Uiso 1 2 calc R U P . .
C8 C 0.500000 0.72362(10) 0.50666(8) 0.0256(4) Uani 1 2 d S T P . .
C9 C 0.500000 0.82698(11) 0.50816(7) 0.0266(4) Uani 1 2 d S T P . .
C10 C 0.500000 0.87171(11) 0.56970(8) 0.0300(4) Uani 1 2 d S T P . .
H10 H 0.500000 0.941386 0.572744 0.036 Uiso 1 2 calc R U P . .
C11 C 0.500000 0.81581(11) 0.62640(8) 0.0290(4) Uani 1 2 d S T P . .
H11 H 0.500000 0.848418 0.667724 0.035 Uiso 1 2 calc R U P . .
N1 N 0.500000 0.67141(10) 0.44440(6) 0.0285(3) Uani 1 2 d S T P . .
O1 O 0.500000 0.58192(8) 0.44429(6) 0.0386(4) Uani 1 2 d S T P . .
O2 O 0.500000 0.72016(8) 0.39245(5) 0.0350(3) Uani 1 2 d S T P . .
O3 O 0.500000 0.88528(8) 0.45455(6) 0.0333(3) Uani 1 2 d S T P . .
H1 H 0.500000 0.8404(19) 0.4205(12) 0.050 Uiso 1 2 d S U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.5270(19) . ?
C1 C5 1.5380(17) . ?
C1 C2 1.5455(15) . ?
C1 C2 1.5456(15) 12_655 ?
C2 C3 1.5350(13) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.529(2) . ?
C3 H3 1.0000 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.386(2) . ?
C6 C11 1.408(2) . ?
C7 C8 1.394(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.407(2) . ?
C8 N1 1.4513(18) . ?
C9 O3 1.3479(17) . ?
C9 C10 1.391(2) . ?
C10 C11 1.381(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
N1 O1 1.2175(18) . ?
N1 O2 1.2471(17) . ?
O3 H1 0.92(3) . ?

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 C1 C5 111.62(12) . . ?
C6 C1 C2 109.92(7) . . ?
C5 C1 C2 108.28(8) . . ?
C6 C1 C2 109.92(7) . 12_655 ?
C5 C1 C2 108.28(8) . 12_655 ?
C2 C1 C2 108.75(13) . 12_655 ?
C3 C2 C1 110.16(10) . . ?
C3 C2 H2A 109.6 . . ?
C1 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
C4 C3 C2 109.90(10) . 10_557 ?
C4 C3 C2 109.90(10) . . ?
C2 C3 C2 109.17(12) 10_557 . ?
C4 C3 H3 109.3 . . ?
C2 C3 H3 109.3 10_557 . ?
C2 C3 H3 109.3 . . ?
C3 C4 C3 109.25(18) 3_656 . ?
C3 C4 H4A 109.8 3_656 . ?
C3 C4 H4A 109.8 . . ?
C3 C4 H4B 109.8 3_656 . ?
C3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.3 . . ?
C1 C5 C1 111.89(16) 10_557 . ?
C1 C5 H5A 109.2 10_557 . ?
C1 C5 H5A 109.2 . . ?
C1 C5 H5B 109.2 10_557 . ?
C1 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C7 C6 C11 116.97(13) . . ?
C7 C6 C1 119.62(13) . . ?
C11 C6 C1 123.41(13) . . ?
C6 C7 C8 120.81(14) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C7 C8 C9 121.90(13) . . ?
C7 C8 N1 117.56(13) . . ?
C9 C8 N1 120.54(13) . . ?
O3 C9 C10 118.01(14) . . ?
O3 C9 C8 124.81(14) . . ?
C10 C9 C8 117.18(14) . . ?
C11 C10 C9 120.65(14) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C6 122.49(14) . . ?
C10 C11 H11 118.8 . . ?
C6 C11 H11 118.8 . . ?
O1 N1 O2 122.02(13) . . ?
O1 N1 C8 119.41(12) . . ?
O2 N1 C8 118.57(13) . . ?
C9 O3 H1 102.5(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 178.81(10) . . . . ?
C5 C1 C2 C3 -59.02(13) . . . . ?
C2 C1 C2 C3 58.43(14) 12_655 . . . ?
C1 C2 C3 C4 -59.87(13) . . . . ?
C1 C2 C3 C2 60.74(17) . . . 10_557 ?
C2 C3 C4 C3 -60.09(9) 10_557 . . 3_656 ?
C2 C3 C4 C3 60.08(9) . . . 3_656 ?
C6 C1 C5 C1 180.000(0) . . . 10_557 ?
C2 C1 C5 C1 58.88(8) . . . 10_557 ?
C2 C1 C5 C1 -58.88(8) 12_655 . . 10_557 ?
C5 C1 C6 C7 180.000(1) . . . . ?
C2 C1 C6 C7 -59.84(8) . . . . ?
C2 C1 C6 C7 59.84(8) 12_655 . . . ?
C5 C1 C6 C11 0.000(1) . . . . ?
C2 C1 C6 C11 120.16(8) . . . . ?
C2 C1 C6 C11 -120.16(8) 12_655 . . . ?
C11 C6 C7 C8 0.000(1) . . . . ?
C1 C6 C7 C8 180.000(1) . . . . ?
C6 C7 C8 C9 0.000(1) . . . . ?
C6 C7 C8 N1 180.000(1) . . . . ?
C7 C8 C9 O3 180.000(1) . . . . ?
N1 C8 C9 O3 0.000(1) . . . . ?
C7 C8 C9 C10 0.000(1) . . . . ?
N1 C8 C9 C10 180.000(1) . . . . ?
O3 C9 C10 C11 180.000(1) . . . . ?
C8 C9 C10 C11 0.000(1) . . . . ?
C9 C10 C11 C6 0.000(1) . . . . ?
C7 C6 C11 C10 0.000(1) . . . . ?
C1 C6 C11 C10 180.000(1) . . . . ?
C7 C8 N1 O1 0.000(1) . . . . ?
C9 C8 N1 O1 180.000(1) . . . . ?
C7 C8 N1 O2 180.000(1) . . . . ?
C9 C8 N1 O2 0.000(1) . . . . ?

_refine_diff_density_max         0.246
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_3a
_database_code_depnum_ccdc_archive 'CCDC 2267704'
loop_
_audit_author_name
_audit_author_address
'Masatoshi Kawahata'
;Showa Pharmaceutical University
Japan
;
_audit_update_record             
;
2023-06-06 deposited with the CCDC.	2023-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H30 N2 O6'
_chemical_formula_weight         466.52

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                   7.1643(12)
_cell_length_b                   9.8755(16)
_cell_length_c                   17.073(3)
_cell_angle_alpha                84.131(5)
_cell_angle_beta                 85.474(5)
_cell_angle_gamma                72.254(5)
_cell_volume                     1142.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9928
_cell_measurement_theta_min      4.72
_cell_measurement_theta_max      78.97

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.792
_shelx_estimated_absorpt_T_min   0.897
_shelx_estimated_absorpt_T_max   0.939
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8698
_exptl_absorpt_correction_T_max  0.9424
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            16106
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.717
_diffrn_reflns_theta_max         78.958
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             4521
_reflns_number_gt                4225
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_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)+(0.0412P)²+0.4022P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4521
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0920
_refine_ls_wR_factor_gt          0.0905
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.35294(14) 0.84078(10) 0.27135(6) 0.0150(2) Uani 1 1 d . . . . .
C2 C 0.55074(14) 0.72405(10) 0.25679(6) 0.0142(2) Uani 1 1 d . . . . .
H2A H 0.612244 0.687384 0.307715 0.017 Uiso 1 1 calc R U . . .
H2B H 0.640660 0.766334 0.222884 0.017 Uiso 1 1 calc R U . . .
C3 C 0.52053(14) 0.59876(10) 0.21655(6) 0.0142(2) Uani 1 1 d . . . . .
C4 C 0.37668(15) 0.53358(10) 0.26788(6) 0.0168(2) Uani 1 1 d . . . . .
H4A H 0.354464 0.455980 0.241044 0.020 Uiso 1 1 calc R U . . .
H4B H 0.433921 0.492425 0.319091 0.020 Uiso 1 1 calc R U . . .
C5 C 0.18081(14) 0.64906(11) 0.28182(6) 0.0177(2) Uani 1 1 d . . . . .
H5 H 0.090820 0.606335 0.316577 0.021 Uiso 1 1 calc R U . . .
C6 C 0.21644(15) 0.76969(11) 0.32262(6) 0.0173(2) Uani 1 1 d . . . . .
H6A H 0.275970 0.730727 0.373688 0.021 Uiso 1 1 calc R U . . .
H6B H 0.089308 0.842249 0.333478 0.021 Uiso 1 1 calc R U . . .
C7 C 0.42322(14) 0.66127(11) 0.13789(6) 0.0163(2) Uani 1 1 d . . . . .
H7A H 0.511158 0.704846 0.103611 0.020 Uiso 1 1 calc R U . . .
H7B H 0.403246 0.583584 0.110418 0.020 Uiso 1 1 calc R U . . .
C8 C 0.22462(14) 0.77456(11) 0.15201(6) 0.0171(2) Uani 1 1 d . . . . .
H8 H 0.165280 0.812445 0.100132 0.021 Uiso 1 1 calc R U . . .
C9 C 0.25566(14) 0.89750(10) 0.19207(6) 0.0166(2) Uani 1 1 d . . . . .
H9A H 0.127769 0.970228 0.201430 0.020 Uiso 1 1 calc R U . . .
H9B H 0.340299 0.943179 0.157224 0.020 Uiso 1 1 calc R U . . .
C10 C 0.08601(15) 0.70822(11) 0.20359(6) 0.0194(2) Uani 1 1 d . . . . .
H10A H -0.041713 0.781192 0.212850 0.023 Uiso 1 1 calc R U . . .
H10B H 0.062808 0.630636 0.177075 0.023 Uiso 1 1 calc R U . . .
C11 C 0.38911(14) 0.96022(10) 0.31328(6) 0.0170(2) Uani 1 1 d . . . . .
C12 C 0.50737(15) 1.04482(11) 0.27861(7) 0.0192(2) Uani 1 1 d . . . . .
C13 C 0.54161(17) 1.15078(11) 0.31918(7) 0.0249(2) Uani 1 1 d . . . . .
H13 H 0.622762 1.204988 0.294918 0.030 Uiso 1 1 calc R U . . .
C14 C 0.45875(17) 1.17717(12) 0.39393(7) 0.0270(3) Uani 1 1 d . . . . .
H14 H 0.481709 1.248878 0.421558 0.032 Uiso 1 1 calc R U . . .
C15 C 0.34201(16) 1.09683(12) 0.42736(7) 0.0235(2) Uani 1 1 d . . . . .
C16 C 0.30724(15) 0.99019(11) 0.38835(6) 0.0199(2) Uani 1 1 d . . . . .
H16 H 0.225923 0.936991 0.413647 0.024 Uiso 1 1 calc R U . . .
C17 C 0.67909(17) 1.11404(12) 0.16171(7) 0.0262(3) Uani 1 1 d . . . . .
H17A H 0.800874 1.108934 0.187104 0.031 Uiso 1 1 calc R U . . .
H17B H 0.591875 1.213549 0.160390 0.031 Uiso 1 1 calc R U . . .
C18 C 0.7259(2) 1.06687(15) 0.07975(8) 0.0351(3) Uani 1 1 d . . . . .
H18A H 0.603758 1.076652 0.054515 0.053 Uiso 1 1 calc R U . . .
H18B H 0.807079 0.966871 0.082156 0.053 Uiso 1 1 calc R U . . .
H18C H 0.797531 1.126280 0.049036 0.053 Uiso 1 1 calc R U . . .
C19 C 0.71989(14) 0.48630(10) 0.20323(6) 0.0147(2) Uani 1 1 d . . . . .
C20 C 0.84000(15) 0.41187(10) 0.26594(6) 0.0160(2) Uani 1 1 d . . . . .
C21 C 1.02392(15) 0.31340(11) 0.25157(6) 0.0190(2) Uani 1 1 d . . . . .
H21 H 1.100747 0.265133 0.294612 0.023 Uiso 1 1 calc R U . . .
C22 C 1.09482(15) 0.28572(11) 0.17535(7) 0.0198(2) Uani 1 1 d . . . . .
H22 H 1.220693 0.220470 0.165171 0.024 Uiso 1 1 calc R U . . .
C23 C 0.97757(15) 0.35553(11) 0.11464(6) 0.0183(2) Uani 1 1 d . . . . .
C24 C 0.79414(15) 0.45383(10) 0.12758(6) 0.0165(2) Uani 1 1 d . . . . .
H24 H 0.718390 0.499530 0.083800 0.020 Uiso 1 1 calc R U . . .
C25 C 0.89064(16) 0.37026(12) 0.40474(6) 0.0212(2) Uani 1 1 d . . . . .
H25A H 1.017637 0.391521 0.398112 0.025 Uiso 1 1 calc R U . . .
H25B H 0.916818 0.265655 0.406262 0.025 Uiso 1 1 calc R U . . .
C26 C 0.78280(18) 0.42511(13) 0.47952(7) 0.0275(3) Uani 1 1 d . . . . .
H26A H 0.749514 0.529369 0.475816 0.041 Uiso 1 1 calc R U . . .
H26B H 0.866242 0.384642 0.524109 0.041 Uiso 1 1 calc R U . . .
H26C H 0.662214 0.397140 0.487493 0.041 Uiso 1 1 calc R U . . .
N1 N 0.24849(15) 1.12393(11) 0.50590(6) 0.0294(2) Uani 1 1 d . . . . .
N2 N 1.04804(14) 0.32551(10) 0.03385(6) 0.0232(2) Uani 1 1 d . . . . .
O1 O 0.27300(17) 1.22210(10) 0.53878(6) 0.0449(3) Uani 1 1 d . . . . .
O2 O 0.14991(14) 1.04849(12) 0.53561(6) 0.0403(2) Uani 1 1 d . . . . .
O3 O 0.58273(11) 1.01876(8) 0.20451(5) 0.02161(18) Uani 1 1 d . . . . .
O4 O 1.21950(14) 0.25316(11) 0.02233(6) 0.0414(3) Uani 1 1 d . . . . .
O5 O 0.93333(13) 0.37342(9) -0.01905(5) 0.02814(19) Uani 1 1 d . . . . .
O6 O 0.76853(11) 0.44035(8) 0.34047(4) 0.01884(17) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C11 1.5360(14) . ?
C1 C6 1.5405(13) . ?
C1 C9 1.5450(14) . ?
C1 C2 1.5511(13) . ?
C2 C3 1.5524(13) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C19 1.5357(13) . ?
C3 C7 1.5449(13) . ?
C3 C4 1.5463(13) . ?
C4 C5 1.5342(14) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.5257(15) . ?
C5 C6 1.5338(14) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.5378(13) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C10 1.5269(14) . ?
C8 C9 1.5329(14) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C16 1.3883(15) . ?
C11 C12 1.4204(15) . ?
C12 O3 1.3537(14) . ?
C12 C13 1.4022(15) . ?
C13 C14 1.3796(18) . ?
C13 H13 0.9500 . ?
C14 C15 1.3752(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.3943(15) . ?
C15 N1 1.4633(15) . ?
C16 H16 0.9500 . ?
C17 O3 1.4393(13) . ?
C17 C18 1.5006(19) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C24 1.3879(14) . ?
C19 C20 1.4234(14) . ?
C20 O6 1.3574(13) . ?
C20 C21 1.3996(14) . ?
C21 C22 1.3820(15) . ?
C21 H21 0.9500 . ?
C22 C23 1.3760(15) . ?
C22 H22 0.9500 . ?
C23 C24 1.3922(14) . ?
C23 N2 1.4587(14) . ?
C24 H24 0.9500 . ?
C25 O6 1.4407(12) . ?
C25 C26 1.5003(16) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
N1 O2 1.2239(15) . ?
N1 O1 1.2315(14) . ?
N2 O5 1.2279(13) . ?
N2 O4 1.2304(13) . ?

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
C11 C1 C6 110.93(8) . . ?
C11 C1 C9 111.88(8) . . ?
C6 C1 C9 107.37(8) . . ?
C11 C1 C2 109.40(8) . . ?
C6 C1 C2 107.59(8) . . ?
C9 C1 C2 109.56(8) . . ?
C1 C2 C3 111.23(8) . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C19 C3 C7 111.56(8) . . ?
C19 C3 C4 111.10(8) . . ?
C7 C3 C4 107.24(8) . . ?
C19 C3 C2 109.33(8) . . ?
C7 C3 C2 107.45(8) . . ?
C4 C3 C2 110.08(8) . . ?
C5 C4 C3 109.91(8) . . ?
C5 C4 H4A 109.7 . . ?
C3 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C10 C5 C6 109.84(8) . . ?
C10 C5 C4 110.22(8) . . ?
C6 C5 C4 109.44(8) . . ?
C10 C5 H5 109.1 . . ?
C6 C5 H5 109.1 . . ?
C4 C5 H5 109.1 . . ?
C5 C6 C1 111.49(8) . . ?
C5 C6 H6A 109.3 . . ?
C1 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C1 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 C3 111.02(8) . . ?
C8 C7 H7A 109.4 . . ?
C3 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C3 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C10 C8 C9 110.00(8) . . ?
C10 C8 C7 110.04(8) . . ?
C9 C8 C7 109.63(8) . . ?
C10 C8 H8 109.1 . . ?
C9 C8 H8 109.1 . . ?
C7 C8 H8 109.1 . . ?
C8 C9 C1 110.02(8) . . ?
C8 C9 H9A 109.7 . . ?
C1 C9 H9A 109.7 . . ?
C8 C9 H9B 109.7 . . ?
C1 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C5 C10 C8 108.16(8) . . ?
C5 C10 H10A 110.1 . . ?
C8 C10 H10A 110.1 . . ?
C5 C10 H10B 110.1 . . ?
C8 C10 H10B 110.1 . . ?
H10A C10 H10B 108.4 . . ?
C16 C11 C12 116.39(9) . . ?
C16 C11 C1 120.94(9) . . ?
C12 C11 C1 122.66(9) . . ?
O3 C12 C13 122.10(10) . . ?
O3 C12 C11 116.57(9) . . ?
C13 C12 C11 121.33(10) . . ?
C14 C13 C12 120.73(11) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 118.17(10) . . ?
C15 C14 H14 120.9 . . ?
C13 C14 H14 120.9 . . ?
C14 C15 C16 122.06(11) . . ?
C14 C15 N1 119.64(10) . . ?
C16 C15 N1 118.29(11) . . ?
C11 C16 C15 121.31(10) . . ?
C11 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
O3 C17 C18 106.64(9) . . ?
O3 C17 H17A 110.4 . . ?
C18 C17 H17A 110.4 . . ?
O3 C17 H17B 110.4 . . ?
C18 C17 H17B 110.4 . . ?
H17A C17 H17B 108.6 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C24 C19 C20 116.24(9) . . ?
C24 C19 C3 120.73(9) . . ?
C20 C19 C3 123.02(9) . . ?
O6 C20 C21 121.30(9) . . ?
O6 C20 C19 117.15(9) . . ?
C21 C20 C19 121.55(9) . . ?
C22 C21 C20 120.63(10) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C23 C22 C21 117.98(9) . . ?
C23 C22 H22 121.0 . . ?
C21 C22 H22 121.0 . . ?
C22 C23 C24 122.35(10) . . ?
C22 C23 N2 118.81(9) . . ?
C24 C23 N2 118.84(10) . . ?
C19 C24 C23 121.23(10) . . ?
C19 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
O6 C25 C26 107.48(9) . . ?
O6 C25 H25A 110.2 . . ?
C26 C25 H25A 110.2 . . ?
O6 C25 H25B 110.2 . . ?
C26 C25 H25B 110.2 . . ?
H25A C25 H25B 108.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O2 N1 O1 123.28(11) . . ?
O2 N1 C15 118.65(10) . . ?
O1 N1 C15 118.07(11) . . ?
O5 N2 O4 123.42(10) . . ?
O5 N2 C23 118.40(9) . . ?
O4 N2 C23 118.18(10) . . ?
C12 O3 C17 119.28(8) . . ?
C20 O6 C25 118.11(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 C1 C2 C3 178.39(8) . . . . ?
C6 C1 C2 C3 57.80(10) . . . . ?
C9 C1 C2 C3 -58.63(10) . . . . ?
C1 C2 C3 C19 179.90(8) . . . . ?
C1 C2 C3 C7 58.67(10) . . . . ?
C1 C2 C3 C4 -57.80(10) . . . . ?
C19 C3 C4 C5 178.64(8) . . . . ?
C7 C3 C4 C5 -59.21(10) . . . . ?
C2 C3 C4 C5 57.39(10) . . . . ?
C3 C4 C5 C10 62.15(10) . . . . ?
C3 C4 C5 C6 -58.75(11) . . . . ?
C10 C5 C6 C1 -59.90(10) . . . . ?
C4 C5 C6 C1 61.23(11) . . . . ?
C11 C1 C6 C5 -179.39(8) . . . . ?
C9 C1 C6 C5 58.09(10) . . . . ?
C2 C1 C6 C5 -59.77(10) . . . . ?
C19 C3 C7 C8 -179.53(8) . . . . ?
C4 C3 C7 C8 58.60(10) . . . . ?
C2 C3 C7 C8 -59.72(10) . . . . ?
C3 C7 C8 C10 -60.13(10) . . . . ?
C3 C7 C8 C9 60.97(10) . . . . ?
C10 C8 C9 C1 62.10(10) . . . . ?
C7 C8 C9 C1 -59.03(10) . . . . ?
C11 C1 C9 C8 179.36(8) . . . . ?
C6 C1 C9 C8 -58.71(10) . . . . ?
C2 C1 C9 C8 57.85(10) . . . . ?
C6 C5 C10 C8 59.70(10) . . . . ?
C4 C5 C10 C8 -60.96(10) . . . . ?
C9 C8 C10 C5 -61.35(10) . . . . ?
C7 C8 C10 C5 59.53(11) . . . . ?
C6 C1 C11 C16 1.45(13) . . . . ?
C9 C1 C11 C16 121.32(10) . . . . ?
C2 C1 C11 C16 -117.08(10) . . . . ?
C6 C1 C11 C12 -179.00(9) . . . . ?
C9 C1 C11 C12 -59.13(12) . . . . ?
C2 C1 C11 C12 62.47(12) . . . . ?
C16 C11 C12 O3 -178.12(8) . . . . ?
C1 C11 C12 O3 2.32(14) . . . . ?
C16 C11 C12 C13 1.17(14) . . . . ?
C1 C11 C12 C13 -178.40(9) . . . . ?
O3 C12 C13 C14 178.39(10) . . . . ?
C11 C12 C13 C14 -0.86(16) . . . . ?
C12 C13 C14 C15 -0.01(16) . . . . ?
C13 C14 C15 C16 0.53(16) . . . . ?
C13 C14 C15 N1 -178.75(10) . . . . ?
C12 C11 C16 C15 -0.66(14) . . . . ?
C1 C11 C16 C15 178.91(9) . . . . ?
C14 C15 C16 C11 -0.18(16) . . . . ?
N1 C15 C16 C11 179.11(9) . . . . ?
C7 C3 C19 C24 1.31(12) . . . . ?
C4 C3 C19 C24 120.92(10) . . . . ?
C2 C3 C19 C24 -117.39(10) . . . . ?
C7 C3 C19 C20 -179.85(8) . . . . ?
C4 C3 C19 C20 -60.24(12) . . . . ?
C2 C3 C19 C20 61.45(11) . . . . ?
C24 C19 C20 O6 -178.92(8) . . . . ?
C3 C19 C20 O6 2.19(14) . . . . ?
C24 C19 C20 C21 1.04(14) . . . . ?
C3 C19 C20 C21 -177.85(9) . . . . ?
O6 C20 C21 C22 -179.89(9) . . . . ?
C19 C20 C21 C22 0.15(15) . . . . ?
C20 C21 C22 C23 -1.31(15) . . . . ?
C21 C22 C23 C24 1.30(15) . . . . ?
C21 C22 C23 N2 -178.72(9) . . . . ?
C20 C19 C24 C23 -1.07(14) . . . . ?
C3 C19 C24 C23 177.85(9) . . . . ?
C22 C23 C24 C19 -0.08(15) . . . . ?
N2 C23 C24 C19 179.94(9) . . . . ?
C14 C15 N1 O2 -177.85(10) . . . . ?
C16 C15 N1 O2 2.85(15) . . . . ?
C14 C15 N1 O1 2.25(15) . . . . ?
C16 C15 N1 O1 -177.05(10) . . . . ?
C22 C23 N2 O5 170.60(9) . . . . ?
C24 C23 N2 O5 -9.42(14) . . . . ?
C22 C23 N2 O4 -9.26(15) . . . . ?
C24 C23 N2 O4 170.71(10) . . . . ?
C13 C12 O3 C17 -8.41(14) . . . . ?
C11 C12 O3 C17 170.87(9) . . . . ?
C18 C17 O3 C12 -173.91(9) . . . . ?
C21 C20 O6 C25 2.31(14) . . . . ?
C19 C20 O6 C25 -177.73(8) . . . . ?
C26 C25 O6 C20 177.22(9) . . . . ?

_refine_diff_density_max         0.309
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.038

