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

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

data_1a
_database_code_depnum_ccdc_archive 'CCDC 2455712'
loop_
_audit_author_name
_audit_author_address
'Masatoshi Kawahata'
;Showa Pharmaceutical University
Japan
;
_audit_update_record             
;
2025-10-06 deposited with the CCDC.	2025-10-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C64 H84 N4 O17'
_chemical_formula_weight         1181.35

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                   13.651(2)
_cell_length_b                   14.252(3)
_cell_length_c                   15.902(3)
_cell_angle_alpha                88.819(9)
_cell_angle_beta                 81.557(8)
_cell_angle_gamma                74.642(8)
_cell_volume                     2950.5(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9889
_cell_measurement_theta_min      3.22
_cell_measurement_theta_max      72.68

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.791
_shelx_estimated_absorpt_T_min   0.918
_shelx_estimated_absorpt_T_max   0.925
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5721
_exptl_absorpt_correction_T_max  0.7536
_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                   'sealed x-ray tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41702
_diffrn_reflns_av_unetI/netI     0.0661
_diffrn_reflns_av_R_equivalents  0.0882
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.810
_diffrn_reflns_theta_max         72.670
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measured_fraction_theta_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_point_group_measured_fraction_full 0.964
_reflns_number_total             11076
_reflns_number_gt                8892
_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       'Bruker APEX6'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_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)+(0.1195P)²+1.0031P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0139(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         11076
_refine_ls_number_parameters     889
_refine_ls_number_restraints     153
_refine_ls_R_factor_all          0.0946
_refine_ls_R_factor_gt           0.0735
_refine_ls_wR_factor_ref         0.1989
_refine_ls_wR_factor_gt          0.1864
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.114
_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 0.99461(15) 0.31248(15) 0.31994(13) 0.0209(4) Uani 1 1 d . . . . .
C2 C 0.92807(15) 0.25398(15) 0.28503(13) 0.0203(4) Uani 1 1 d . . . . .
H2A H 0.856574 0.294901 0.288364 0.024 Uiso 1 1 calc R U . . .
H2B H 0.927275 0.196150 0.320429 0.024 Uiso 1 1 calc R U . . .
C3 C 0.97091(15) 0.22091(15) 0.19130(13) 0.0207(4) Uani 1 1 d . . . . .
C4 C 0.97349(15) 0.31007(15) 0.13507(13) 0.0220(4) Uani 1 1 d . . . . .
H4A H 1.002924 0.288197 0.075854 0.026 Uiso 1 1 calc R U . . .
H4B H 0.902758 0.351584 0.134963 0.026 Uiso 1 1 calc R U . . .
C5 C 1.03880(16) 0.36874(16) 0.16941(14) 0.0239(4) Uani 1 1 d . . . . .
H5 H 1.037958 0.427663 0.133989 0.029 Uiso 1 1 calc R U . . .
C6 C 0.99395(16) 0.40089(15) 0.26206(13) 0.0222(4) Uani 1 1 d . . . . .
H6A H 0.922576 0.441750 0.264196 0.027 Uiso 1 1 calc R U . . .
H6B H 1.034786 0.440784 0.283381 0.027 Uiso 1 1 calc R U . . .
C7 C 1.10680(15) 0.24972(16) 0.31344(14) 0.0240(4) Uani 1 1 d . . . . .
H7A H 1.149477 0.287736 0.334707 0.029 Uiso 1 1 calc R U . . .
H7B H 1.109594 0.191630 0.349180 0.029 Uiso 1 1 calc R U . . .
C8 C 1.14943(15) 0.21772(16) 0.22068(14) 0.0255(5) Uani 1 1 d . . . . .
H8 H 1.221341 0.175774 0.217789 0.031 Uiso 1 1 calc R U . . .
C9 C 1.08304(15) 0.15913(16) 0.18831(14) 0.0241(4) Uani 1 1 d . . . . .
H9A H 1.084393 0.100987 0.223735 0.029 Uiso 1 1 calc R U . . .
H9B H 1.111724 0.136661 0.129106 0.029 Uiso 1 1 calc R U . . .
C10 C 1.14976(16) 0.30632(17) 0.16542(15) 0.0279(5) Uani 1 1 d . . . . .
H10A H 1.178953 0.285325 0.105969 0.034 Uiso 1 1 calc R U . . .
H10B H 1.192430 0.344540 0.186409 0.034 Uiso 1 1 calc R U . . .
C11 C 0.95000(15) 0.34420(16) 0.41258(13) 0.0228(4) Uani 1 1 d . . . . .
C12 C 0.94754(17) 0.27635(17) 0.47899(14) 0.0274(5) Uani 1 1 d . . . . .
C13 C 0.90729(19) 0.30707(19) 0.56329(15) 0.0329(5) Uani 1 1 d . . . . .
H13 H 0.907180 0.259917 0.606377 0.039 Uiso 1 1 calc R U . . .
C14 C 0.86802(18) 0.40415(18) 0.58459(14) 0.0311(5) Uani 1 1 d . . . . .
H14 H 0.840110 0.425039 0.641494 0.037 Uiso 1 1 calc R U . . .
C15 C 0.87075(16) 0.47003(16) 0.52009(14) 0.0253(5) Uani 1 1 d . . . . .
C16 C 0.91111(15) 0.44172(16) 0.43592(14) 0.0228(4) Uani 1 1 d . . . . .
H16 H 0.911964 0.489990 0.393920 0.027 Uiso 1 1 calc R U . . .
C17 C 0.90390(15) 0.16302(15) 0.15869(12) 0.0208(4) Uani 1 1 d . . . . .
C18 C 0.79754(16) 0.20336(15) 0.15576(13) 0.0228(4) Uani 1 1 d . . . . .
C19 C 0.73790(17) 0.14817(17) 0.12668(14) 0.0266(5) Uani 1 1 d . . . . .
H19 H 0.666766 0.176604 0.125840 0.032 Uiso 1 1 calc R U . . .
C20 C 0.78100(18) 0.05337(17) 0.09935(14) 0.0268(5) Uani 1 1 d . . . . .
H20 H 0.740618 0.015711 0.079787 0.032 Uiso 1 1 calc R U . . .
C21 C 0.88499(17) 0.01430(16) 0.10113(13) 0.0258(5) Uani 1 1 d . . . . .
C22 C 0.94514(16) 0.06754(16) 0.13075(13) 0.0239(4) Uani 1 1 d . . . . .
H22 H 1.015975 0.037766 0.131826 0.029 Uiso 1 1 calc R U . . .
N1 N 0.82788(14) 0.57259(15) 0.54094(13) 0.0281(4) Uani 1 1 d . . . . .
N2 N 0.93360(16) -0.08570(14) 0.07260(12) 0.0302(4) Uani 1 1 d . . . . .
O1 O 0.98436(15) 0.18017(12) 0.46091(11) 0.0346(4) Uani 1 1 d . . . . .
H1 H 1.000(3) 0.1528(15) 0.502(2) 0.052 Uiso 1 1 calc R U . . .
O2 O 0.77936(13) 0.59515(13) 0.61339(11) 0.0364(4) Uani 1 1 d . . . . .
O3 O 0.83930(13) 0.63286(12) 0.48653(12) 0.0347(4) Uani 1 1 d . . . . .
O4 O 0.75429(12) 0.29691(11) 0.17985(10) 0.0261(3) Uani 1 1 d . . . . .
H4 H 0.687(3) 0.3114(8) 0.1775(19) 0.039 Uiso 1 1 calc R U . . .
O5 O 0.88373(14) -0.12841(13) 0.03633(11) 0.0372(4) Uani 1 1 d . . . . .
O6 O 1.02260(15) -0.12283(13) 0.08446(14) 0.0452(5) Uani 1 1 d . . . . .
C23 C 0.67621(15) 0.62327(15) 0.25395(13) 0.0221(4) Uani 1 1 d . . . . .
C24 C 0.58245(15) 0.70341(15) 0.23109(13) 0.0215(4) Uani 1 1 d . . . . .
H24A H 0.523504 0.675216 0.231099 0.026 Uiso 1 1 calc R U . . .
H24B H 0.562567 0.756087 0.274865 0.026 Uiso 1 1 calc R U . . .
C25 C 0.60700(15) 0.74641(15) 0.14307(13) 0.0210(4) Uani 1 1 d . . . . .
C26 C 0.70049(15) 0.78818(15) 0.14467(15) 0.0246(4) Uani 1 1 d . . . . .
H26A H 0.717661 0.816294 0.088755 0.030 Uiso 1 1 calc R U . . .
H26B H 0.682803 0.840909 0.188279 0.030 Uiso 1 1 calc R U . . .
C27 C 0.79432(15) 0.70822(16) 0.16479(15) 0.0253(5) Uani 1 1 d . . . . .
H27 H 0.853364 0.737285 0.165257 0.030 Uiso 1 1 calc R U . . .
C28 C 0.76952(15) 0.66662(15) 0.25195(14) 0.0237(4) Uani 1 1 d . . . . .
H28A H 0.753663 0.718664 0.296029 0.028 Uiso 1 1 calc R U . . .
H28B H 0.829906 0.615226 0.264678 0.028 Uiso 1 1 calc R U . . .
C29 C 0.70455(15) 0.54450(15) 0.18318(14) 0.0228(4) Uani 1 1 d . . . . .
H29A H 0.763886 0.491791 0.195817 0.027 Uiso 1 1 calc R U . . .
H29B H 0.645970 0.516075 0.182043 0.027 Uiso 1 1 calc R U . . .
C30 C 0.73165(16) 0.58593(15) 0.09570(14) 0.0246(5) Uani 1 1 d . . . . .
H30 H 0.749977 0.532422 0.051862 0.029 Uiso 1 1 calc R U . . .
C31 C 0.63897(15) 0.66585(15) 0.07359(13) 0.0231(4) Uani 1 1 d . . . . .
H31A H 0.580894 0.637568 0.069606 0.028 Uiso 1 1 calc R U . . .
H31B H 0.657451 0.693736 0.017850 0.028 Uiso 1 1 calc R U . . .
C32 C 0.82361(16) 0.62797(17) 0.09619(14) 0.0262(5) Uani 1 1 d . . . . .
H32A H 0.841390 0.655035 0.039920 0.031 Uiso 1 1 calc R U . . .
H32B H 0.883954 0.576312 0.108600 0.031 Uiso 1 1 calc R U . . .
C33 C 0.65165(15) 0.58214(18) 0.34205(14) 0.0272(5) Uani 1 1 d . . . . .
C34 C 0.62184(16) 0.6417(2) 0.41671(15) 0.0329(5) Uani 1 1 d . . . . .
C35 C 0.60468(19) 0.6004(3) 0.49748(16) 0.0474(8) Uani 1 1 d . . . . .
H35 H 0.584767 0.641519 0.546684 0.057 Uiso 1 1 calc R U . . .
C36 C 0.6161(2) 0.5024(3) 0.50633(18) 0.0483(8) Uani 1 1 d . . . . .
H36 H 0.605604 0.475140 0.560842 0.058 Uiso 1 1 calc R U . . .
C37 C 0.64332(18) 0.4446(2) 0.43373(18) 0.0422(7) Uani 1 1 d . . . . .
C38 C 0.66099(16) 0.48327(19) 0.35289(16) 0.0309(5) Uani 1 1 d . . . . .
H38 H 0.679751 0.440967 0.304431 0.037 Uiso 1 1 calc R U . . .
C39 C 0.51295(15) 0.82653(15) 0.12356(13) 0.0217(4) Uani 1 1 d . . . . .
C40 C 0.41819(15) 0.80718(16) 0.11409(13) 0.0228(4) Uani 1 1 d . . . . .
C41 C 0.33354(15) 0.88235(17) 0.09742(14) 0.0258(5) Uani 1 1 d . . . . .
H41 H 0.271503 0.867229 0.090278 0.031 Uiso 1 1 calc R U . . .
C42 C 0.33872(16) 0.97690(16) 0.09127(14) 0.0255(5) Uani 1 1 d . . . . .
H42 H 0.281130 1.027750 0.080816 0.031 Uiso 1 1 calc R U . . .
C43 C 0.43111(15) 0.99574(15) 0.10085(13) 0.0229(4) Uani 1 1 d . . . . .
C44 C 0.51574(15) 0.92269(15) 0.11675(13) 0.0218(4) Uani 1 1 d . . . . .
H44 H 0.577335 0.939119 0.123140 0.026 Uiso 1 1 calc R U . . .
N3 N 0.65282(18) 0.3398(2) 0.4393(2) 0.0540(7) Uani 1 1 d . U . . .
N4 N 0.43953(13) 1.09562(13) 0.09473(11) 0.0248(4) Uani 1 1 d . . . . .
O7 O 0.61172(14) 0.73729(15) 0.40889(11) 0.0403(5) Uani 1 1 d . . . . .
H7 H 0.601(3) 0.7603(15) 0.451(2) 0.060 Uiso 1 1 calc R U . . .
O8 O 0.6460(3) 0.3070(3) 0.5130(2) 0.0881(10) Uani 1 1 d . U . . .
O9 O 0.66384(19) 0.29203(18) 0.37451(19) 0.0631(6) Uani 1 1 d . U . . .
O10 O 0.41059(12) 0.71490(11) 0.12192(10) 0.0261(3) Uani 1 1 d . . . . .
H10 H 0.349(3) 0.7140(3) 0.121(2) 0.039 Uiso 1 1 calc R U . . .
O11 O 0.36325(12) 1.16009(12) 0.08316(11) 0.0329(4) Uani 1 1 d . . . . .
O12 O 0.52240(12) 1.11119(12) 0.10183(12) 0.0325(4) Uani 1 1 d . . . . .
C45 C 0.4679(2) 0.8935(3) 0.5918(2) 0.0593(9) Uani 1 1 d . . . . .
H45A H 0.415128 0.856992 0.594632 0.071 Uiso 1 1 calc R U . . .
H45B H 0.447363 0.951849 0.556907 0.071 Uiso 1 1 calc R U . . .
C46 C 0.6414(2) 0.8438(2) 0.6032(2) 0.0545(9) Uani 1 1 d . . . . .
H46A H 0.676945 0.891693 0.576984 0.065 Uiso 1 1 calc R U . . .
H46B H 0.692792 0.780491 0.606112 0.065 Uiso 1 1 calc R U . . .
C47 C 0.5860(3) 0.8781(3) 0.6902(2) 0.0616(9) Uani 1 1 d . . . . .
H47A H 0.590471 0.822981 0.729677 0.074 Uiso 1 1 calc R U . . .
H47B H 0.614804 0.927067 0.713531 0.074 Uiso 1 1 calc R U . . .
C48 C 0.4780(4) 0.9217(6) 0.6763(3) 0.138(3) Uani 1 1 d . . . . .
H48A H 0.430378 0.897941 0.719277 0.165 Uiso 1 1 calc R U . . .
H48B H 0.461051 0.993476 0.681778 0.165 Uiso 1 1 calc R U . . .
O13 O 0.56504(18) 0.8342(3) 0.55599(18) 0.0989(13) Uani 1 1 d . . . . .
C49 C 0.18597(16) 0.66758(17) 0.04440(14) 0.0266(5) Uani 1 1 d . . . . .
H49A H 0.241035 0.616136 0.011842 0.032 Uiso 1 1 calc R U . . .
H49B H 0.164421 0.722665 0.006308 0.032 Uiso 1 1 calc R U . . .
C50 C 0.15365(19) 0.69188(19) 0.19277(15) 0.0328(5) Uani 1 1 d . . . . .
H50A H 0.100695 0.754197 0.206354 0.039 Uiso 1 1 calc R U . . .
H50B H 0.191965 0.674115 0.241545 0.039 Uiso 1 1 calc R U . . .
C51 C 0.1051(2) 0.6125(2) 0.17311(17) 0.0368(6) Uani 1 1 d . . . . .
H51A H 0.037034 0.620580 0.208060 0.044 Uiso 1 1 calc R U . . .
H51B H 0.149663 0.547182 0.182444 0.044 Uiso 1 1 calc R U . . .
C52 C 0.09553(18) 0.62832(19) 0.07941(16) 0.0330(5) Uani 1 1 d . . . . .
H52A H 0.099442 0.566359 0.050410 0.040 Uiso 1 1 calc R U . . .
H52B H 0.029779 0.675742 0.072344 0.040 Uiso 1 1 calc R U . . .
O14 O 0.22182(12) 0.69949(14) 0.11689(10) 0.0334(4) Uani 1 1 d . . . . .
C53 C 1.1381(4) 0.1536(3) 0.6164(5) 0.0636(17) Uani 0.858(6) 1 d D . P A 1
H53A H 1.104656 0.211511 0.653543 0.076 Uiso 0.858(6) 1 calc R U P A 1
H53B H 1.170738 0.175001 0.562359 0.076 Uiso 0.858(6) 1 calc R U P A 1
C54 C 1.0813(3) 0.0142(2) 0.6434(2) 0.0451(9) Uani 0.858(6) 1 d D . P A 1
H54A H 1.062062 -0.034884 0.610877 0.054 Uiso 0.858(6) 1 calc R U P A 1
H54B H 1.039625 0.022548 0.700562 0.054 Uiso 0.858(6) 1 calc R U P A 1
C55 C 1.1941(3) -0.0177(3) 0.6509(3) 0.0500(10) Uani 0.858(6) 1 d D . P A 1
H55A H 1.235022 -0.054602 0.599659 0.060 Uiso 0.858(6) 1 calc R U P A 1
H55B H 1.207168 -0.057223 0.701964 0.060 Uiso 0.858(6) 1 calc R U P A 1
C56 C 1.2156(4) 0.0838(4) 0.6587(5) 0.085(2) Uani 0.858(6) 1 d D . P A 1
H56A H 1.209239 0.102655 0.719221 0.102 Uiso 0.858(6) 1 calc R U P A 1
H56B H 1.285732 0.082099 0.630552 0.102 Uiso 0.858(6) 1 calc R U P A 1
O15 O 1.06442(17) 0.10392(15) 0.60061(14) 0.0375(7) Uani 0.858(6) 1 d D . P A 1
C53B C 1.2466(16) 0.092(2) 0.6051(12) 0.064(6) Uani 0.142(6) 1 d D U P A 2
H53C H 1.267940 0.054324 0.550698 0.077 Uiso 0.142(6) 1 calc R U P A 2
H53D H 1.294654 0.132171 0.609095 0.077 Uiso 0.142(6) 1 calc R U P A 2
C54B C 1.1535(19) 0.002(2) 0.669(2) 0.088(7) Uani 0.142(6) 1 d D U P A 2
H54C H 1.137289 -0.041210 0.715090 0.106 Uiso 0.142(6) 1 calc R U P A 2
H54D H 1.156241 -0.029324 0.613219 0.106 Uiso 0.142(6) 1 calc R U P A 2
C55B C 1.0758(19) 0.103(3) 0.678(2) 0.100(7) Uani 0.142(6) 1 d D U P A 2
H55C H 1.065819 0.132012 0.735345 0.120 Uiso 0.142(6) 1 calc R U P A 2
H55D H 1.008692 0.101989 0.661601 0.120 Uiso 0.142(6) 1 calc R U P A 2
C56B C 1.140(2) 0.154(3) 0.609(3) 0.083(7) Uani 0.142(6) 1 d D U P A 2
H56C H 1.115500 0.156263 0.553242 0.100 Uiso 0.142(6) 1 calc R U P A 2
H56D H 1.134776 0.221728 0.627492 0.100 Uiso 0.142(6) 1 calc R U P A 2
O15B O 1.2478(12) 0.0270(17) 0.6750(9) 0.060(5) Uani 0.142(6) 1 d D U P A 2
C57 C 0.6479(4) 0.1256(4) 0.6411(4) 0.0607(14) Uani 0.788(8) 1 d D . P B 1
H57A H 0.610238 0.098699 0.689434 0.073 Uiso 0.788(8) 1 calc R U P B 1
H57B H 0.597502 0.168050 0.608454 0.073 Uiso 0.788(8) 1 calc R U P B 1
C58 C 0.8192(5) 0.0429(6) 0.6017(6) 0.095(2) Uani 0.788(8) 1 d D . P B 1
H58A H 0.857852 0.065911 0.551596 0.115 Uiso 0.788(8) 1 calc R U P B 1
H58B H 0.856097 -0.024856 0.613092 0.115 Uiso 0.788(8) 1 calc R U P B 1
C59 C 0.8086(5) 0.1052(6) 0.6750(5) 0.069(2) Uani 0.788(8) 1 d D . P B 1
H59A H 0.867498 0.134072 0.671666 0.083 Uiso 0.788(8) 1 calc R U P B 1
H59B H 0.804546 0.068213 0.728237 0.083 Uiso 0.788(8) 1 calc R U P B 1
C60 C 0.7128(5) 0.1808(3) 0.6717(3) 0.0492(12) Uani 0.788(8) 1 d D . P B 1
H60A H 0.723594 0.232526 0.631765 0.059 Uiso 0.788(8) 1 calc R U P B 1
H60B H 0.682773 0.210279 0.728647 0.059 Uiso 0.788(8) 1 calc R U P B 1
O16 O 0.7168(3) 0.0478(3) 0.5870(3) 0.0768(14) Uani 0.788(8) 1 d D . P B 1
C57B C 0.8351(12) 0.1074(15) 0.6367(14) 0.058(6) Uani 0.212(8) 1 d D U P B 2
H57C H 0.866166 0.043937 0.661222 0.070 Uiso 0.212(8) 1 calc R U P B 2
H57D H 0.890642 0.140228 0.622227 0.070 Uiso 0.212(8) 1 calc R U P B 2
C58B C 0.6715(17) 0.1613(18) 0.6675(13) 0.091(8) Uani 0.212(8) 1 d D U P B 2
H58C H 0.635125 0.120189 0.703989 0.109 Uiso 0.212(8) 1 calc R U P B 2
H58D H 0.626198 0.228383 0.670127 0.109 Uiso 0.212(8) 1 calc R U P B 2
C59B C 0.6927(19) 0.1246(18) 0.5808(12) 0.096(8) Uani 0.212(8) 1 d D U P B 2
H59C H 0.666048 0.177398 0.542120 0.115 Uiso 0.212(8) 1 calc R U P B 2
H59D H 0.658753 0.072052 0.575608 0.115 Uiso 0.212(8) 1 calc R U P B 2
C60B C 0.804(2) 0.087(2) 0.5581(15) 0.124(10) Uani 0.212(8) 1 d D U P B 2
H60C H 0.824048 0.016481 0.544232 0.148 Uiso 0.212(8) 1 calc R U P B 2
H60D H 0.831332 0.122516 0.510091 0.148 Uiso 0.212(8) 1 calc R U P B 2
O16B O 0.7665(14) 0.1611(13) 0.6994(8) 0.070(5) Uani 0.212(8) 1 d D U P B 2
C61 C 0.5070(3) 0.3764(3) 0.1005(2) 0.0508(8) Uani 0.943(4) 1 d D U P C 1
H61A H 0.496291 0.316632 0.077074 0.061 Uiso 0.943(4) 1 calc R U P C 1
H61B H 0.553686 0.401378 0.057667 0.061 Uiso 0.943(4) 1 calc R U P C 1
C62 C 0.4716(2) 0.3886(3) 0.24934(19) 0.0451(7) Uani 0.943(4) 1 d D U P C 1
H62A H 0.500023 0.411245 0.296561 0.054 Uiso 0.943(4) 1 calc R U P C 1
H62B H 0.439774 0.335966 0.269953 0.054 Uiso 0.943(4) 1 calc R U P C 1
C63 C 0.3936(3) 0.4724(3) 0.2152(3) 0.0669(11) Uani 0.943(4) 1 d D U P C 1
H63A H 0.322926 0.474466 0.242173 0.080 Uiso 0.943(4) 1 calc R U P C 1
H63B H 0.407649 0.535439 0.225862 0.080 Uiso 0.943(4) 1 calc R U P C 1
C64 C 0.4073(3) 0.4508(4) 0.1214(3) 0.0677(11) Uani 0.943(4) 1 d D U P C 1
H64A H 0.350498 0.425770 0.107339 0.081 Uiso 0.943(4) 1 calc R U P C 1
H64B H 0.408053 0.510568 0.088645 0.081 Uiso 0.943(4) 1 calc R U P C 1
O17 O 0.55051(13) 0.35540(14) 0.17783(11) 0.0357(5) Uani 0.943(4) 1 d D U P C 1
C61B C 0.4058(17) 0.480(2) 0.2472(14) 0.008(4) Uani 0.057(4) 1 d D U P C 2
H61C H 0.399174 0.423647 0.282848 0.010 Uiso 0.057(4) 1 calc R U P C 2
H61D H 0.387573 0.540077 0.282707 0.010 Uiso 0.057(4) 1 calc R U P C 2
C62B C 0.3986(17) 0.4067(19) 0.1222(17) 0.008(4) Uani 0.057(4) 1 d D U P C 2
H62C H 0.368579 0.407782 0.069037 0.010 Uiso 0.057(4) 1 calc R U P C 2
H62D H 0.396648 0.345739 0.152529 0.010 Uiso 0.057(4) 1 calc R U P C 2
C63B C 0.5087(17) 0.420(2) 0.1048(16) 0.008(4) Uani 0.057(4) 1 d D U P C 2
H63C H 0.561361 0.356866 0.092746 0.010 Uiso 0.057(4) 1 calc R U P C 2
H63D H 0.516772 0.465341 0.058189 0.010 Uiso 0.057(4) 1 calc R U P C 2
C64B C 0.5094(15) 0.463(2) 0.1927(15) 0.008(4) Uani 0.057(4) 1 d D U P C 2
H64C H 0.561885 0.418130 0.221751 0.010 Uiso 0.057(4) 1 calc R U P C 2
H64D H 0.528108 0.525599 0.185118 0.010 Uiso 0.057(4) 1 calc R U P C 2
O17B O 0.3483(13) 0.4900(13) 0.1743(12) 0.008(4) Uani 0.057(4) 1 d D U P C 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 1.537(3) . ?
C1 C6 1.544(3) . ?
C1 C7 1.545(3) . ?
C1 C2 1.548(2) . ?
C2 C3 1.553(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C17 1.531(3) . ?
C3 C4 1.544(3) . ?
C3 C9 1.545(3) . ?
C4 C5 1.533(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.533(3) . ?
C5 C6 1.539(3) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.535(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C10 1.524(3) . ?
C8 C9 1.529(3) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C16 1.387(3) . ?
C11 C12 1.420(3) . ?
C12 O1 1.350(3) . ?
C12 C13 1.404(3) . ?
C13 C14 1.375(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.379(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.395(3) . ?
C15 N1 1.449(3) . ?
C16 H16 0.9500 . ?
C17 C22 1.383(3) . ?
C17 C18 1.420(3) . ?
C18 O4 1.346(3) . ?
C18 C19 1.400(3) . ?
C19 C20 1.374(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.385(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.389(3) . ?
C21 N2 1.454(3) . ?
C22 H22 0.9500 . ?
N1 O3 1.229(3) . ?
N1 O2 1.244(3) . ?
N2 O6 1.231(3) . ?
N2 O5 1.231(3) . ?
O1 H1 0.78(4) . ?
O4 H4 0.89(3) . ?
C23 C33 1.533(3) . ?
C23 C29 1.540(3) . ?
C23 C28 1.552(3) . ?
C23 C24 1.556(3) . ?
C24 C25 1.544(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C39 1.541(3) . ?
C25 C31 1.541(3) . ?
C25 C26 1.548(3) . ?
C26 C27 1.541(3) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.524(3) . ?
C27 C32 1.529(3) . ?
C27 H27 1.0000 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.533(3) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C32 1.528(3) . ?
C30 C31 1.540(3) . ?
C30 H30 1.0000 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C38 1.390(4) . ?
C33 C34 1.419(3) . ?
C34 O7 1.337(3) . ?
C34 C35 1.416(4) . ?
C35 C36 1.369(5) . ?
C35 H35 0.9500 . ?
C36 C37 1.378(5) . ?
C36 H36 0.9500 . ?
C37 C38 1.401(4) . ?
C37 N3 1.467(4) . ?
C38 H38 0.9500 . ?
C39 C44 1.383(3) . ?
C39 C40 1.421(3) . ?
C40 O10 1.348(3) . ?
C40 C41 1.406(3) . ?
C41 C42 1.369(3) . ?
C41 H41 0.9500 . ?
C42 C43 1.387(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.386(3) . ?
C43 N4 1.458(3) . ?
C44 H44 0.9500 . ?
N3 O9 1.216(4) . ?
N3 O8 1.253(4) . ?
N4 O11 1.227(2) . ?
N4 O12 1.230(2) . ?
O7 H7 0.73(4) . ?
O10 H10 0.85(3) . ?
C45 O13 1.415(4) . ?
C45 C48 1.447(5) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C46 O13 1.406(3) . ?
C46 C47 1.500(5) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C47 C48 1.487(5) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C49 O14 1.442(2) . ?
C49 C52 1.516(3) . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C50 O14 1.433(3) . ?
C50 C51 1.513(3) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C51 C52 1.522(4) . ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?
C53 O15 1.426(5) . ?
C53 C56 1.478(6) . ?
C53 H53A 0.9900 . ?
C53 H53B 0.9900 . ?
C54 O15 1.416(4) . ?
C54 C55 1.506(5) . ?
C54 H54A 0.9900 . ?
C54 H54B 0.9900 . ?
C55 C56 1.562(6) . ?
C55 H55A 0.9900 . ?
C55 H55B 0.9900 . ?
C56 H56A 0.9900 . ?
C56 H56B 0.9900 . ?
C53B O15B 1.429(17) . ?
C53B C56B 1.489(18) . ?
C53B H53C 0.9900 . ?
C53B H53D 0.9900 . ?
C54B O15B 1.439(19) . ?
C54B C55B 1.54(2) . ?
C54B H54C 0.9900 . ?
C54B H54D 0.9900 . ?
C55B C56B 1.59(2) . ?
C55B H55C 0.9900 . ?
C55B H55D 0.9900 . ?
C56B H56C 0.9900 . ?
C56B H56D 0.9900 . ?
C57 O16 1.450(6) . ?
C57 C60 1.466(8) . ?
C57 H57A 0.9900 . ?
C57 H57B 0.9900 . ?
C58 O16 1.434(8) . ?
C58 C59 1.447(9) . ?
C58 H58A 0.9900 . ?
C58 H58B 0.9900 . ?
C59 C60 1.465(8) . ?
C59 H59A 0.9900 . ?
C59 H59B 0.9900 . ?
C60 H60A 0.9900 . ?
C60 H60B 0.9900 . ?
C57B O16B 1.355(16) . ?
C57B C60B 1.438(19) . ?
C57B H57C 0.9900 . ?
C57B H57D 0.9900 . ?
C58B C59B 1.446(18) . ?
C58B O16B 1.460(17) . ?
C58B H58C 0.9900 . ?
C58B H58D 0.9900 . ?
C59B C60B 1.46(2) . ?
C59B H59C 0.9900 . ?
C59B H59D 0.9900 . ?
C60B H60C 0.9900 . ?
C60B H60D 0.9900 . ?
C61 O17 1.435(3) . ?
C61 C64 1.485(5) . ?
C61 H61A 0.9900 . ?
C61 H61B 0.9900 . ?
C62 O17 1.439(3) . ?
C62 C63 1.524(5) . ?
C62 H62A 0.9900 . ?
C62 H62B 0.9900 . ?
C63 C64 1.504(6) . ?
C63 H63A 0.9900 . ?
C63 H63B 0.9900 . ?
C64 H64A 0.9900 . ?
C64 H64B 0.9900 . ?
C61B O17B 1.476(17) . ?
C61B C64B 1.509(18) . ?
C61B H61C 0.9900 . ?
C61B H61D 0.9900 . ?
C62B O17B 1.418(18) . ?
C62B C63B 1.546(19) . ?
C62B H62C 0.9900 . ?
C62B H62D 0.9900 . ?
C63B C64B 1.543(18) . ?
C63B H63C 0.9900 . ?
C63B H63D 0.9900 . ?
C64B H64C 0.9900 . ?
C64B H64D 0.9900 . ?

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 111.63(16) . . ?
C11 C1 C7 110.95(16) . . ?
C6 C1 C7 107.70(17) . . ?
C11 C1 C2 109.47(16) . . ?
C6 C1 C2 107.23(15) . . ?
C7 C1 C2 109.78(16) . . ?
C1 C2 C3 110.84(16) . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C17 C3 C4 110.13(16) . . ?
C17 C3 C9 111.59(16) . . ?
C4 C3 C9 107.11(17) . . ?
C17 C3 C2 109.65(16) . . ?
C4 C3 C2 110.30(16) . . ?
C9 C3 C2 108.01(15) . . ?
C5 C4 C3 109.71(16) . . ?
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 . . ?
C4 C5 C10 109.89(17) . . ?
C4 C5 C6 109.53(17) . . ?
C10 C5 C6 109.68(17) . . ?
C4 C5 H5 109.2 . . ?
C10 C5 H5 109.2 . . ?
C6 C5 H5 109.2 . . ?
C5 C6 C1 111.42(16) . . ?
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 C1 110.13(16) . . ?
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 109.86(17) . . ?
C10 C8 C7 110.27(18) . . ?
C9 C8 C7 109.29(18) . . ?
C10 C8 H8 109.1 . . ?
C9 C8 H8 109.1 . . ?
C7 C8 H8 109.1 . . ?
C8 C9 C3 111.18(16) . . ?
C8 C9 H9A 109.4 . . ?
C3 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C3 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C8 C10 C5 108.37(18) . . ?
C8 C10 H10A 110.0 . . ?
C5 C10 H10A 110.0 . . ?
C8 C10 H10B 110.0 . . ?
C5 C10 H10B 110.0 . . ?
H10A C10 H10B 108.4 . . ?
C16 C11 C12 116.28(19) . . ?
C16 C11 C1 121.3(2) . . ?
C12 C11 C1 122.40(18) . . ?
O1 C12 C13 119.1(2) . . ?
O1 C12 C11 119.5(2) . . ?
C13 C12 C11 121.4(2) . . ?
C14 C13 C12 121.2(2) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 117.4(2) . . ?
C13 C14 H14 121.3 . . ?
C15 C14 H14 121.3 . . ?
C14 C15 C16 122.7(2) . . ?
C14 C15 N1 118.23(19) . . ?
C16 C15 N1 119.0(2) . . ?
C11 C16 C15 121.0(2) . . ?
C11 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C22 C17 C18 116.72(18) . . ?
C22 C17 C3 120.81(18) . . ?
C18 C17 C3 122.47(17) . . ?
O4 C18 C19 119.74(18) . . ?
O4 C18 C17 119.08(17) . . ?
C19 C18 C17 121.17(19) . . ?
C20 C19 C18 120.8(2) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C20 C21 118.09(19) . . ?
C19 C20 H20 121.0 . . ?
C21 C20 H20 121.0 . . ?
C20 C21 C22 121.9(2) . . ?
C20 C21 N2 119.82(19) . . ?
C22 C21 N2 118.3(2) . . ?
C17 C22 C21 121.28(19) . . ?
C17 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
O3 N1 O2 123.13(19) . . ?
O3 N1 C15 119.11(19) . . ?
O2 N1 C15 117.7(2) . . ?
O6 N2 O5 123.31(19) . . ?
O6 N2 C21 118.72(18) . . ?
O5 N2 C21 117.96(19) . . ?
C12 O1 H1 109.5 . . ?
C18 O4 H4 109.5 . . ?
C33 C23 C29 112.22(18) . . ?
C33 C23 C28 109.76(16) . . ?
C29 C23 C28 107.19(16) . . ?
C33 C23 C24 111.15(16) . . ?
C29 C23 C24 106.93(15) . . ?
C28 C23 C24 109.46(17) . . ?
C25 C24 C23 111.53(16) . . ?
C25 C24 H24A 109.3 . . ?
C23 C24 H24A 109.3 . . ?
C25 C24 H24B 109.3 . . ?
C23 C24 H24B 109.3 . . ?
H24A C24 H24B 108.0 . . ?
C39 C25 C31 110.63(16) . . ?
C39 C25 C24 109.87(16) . . ?
C31 C25 C24 110.50(17) . . ?
C39 C25 C26 110.86(17) . . ?
C31 C25 C26 106.90(16) . . ?
C24 C25 C26 108.01(16) . . ?
C27 C26 C25 110.86(17) . . ?
C27 C26 H26A 109.5 . . ?
C25 C26 H26A 109.5 . . ?
C27 C26 H26B 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 108.1 . . ?
C28 C27 C32 110.42(18) . . ?
C28 C27 C26 109.79(17) . . ?
C32 C27 C26 109.58(17) . . ?
C28 C27 H27 109.0 . . ?
C32 C27 H27 109.0 . . ?
C26 C27 H27 109.0 . . ?
C27 C28 C23 110.24(16) . . ?
C27 C28 H28A 109.6 . . ?
C23 C28 H28A 109.6 . . ?
C27 C28 H28B 109.6 . . ?
C23 C28 H28B 109.6 . . ?
H28A C28 H28B 108.1 . . ?
C30 C29 C23 111.75(17) . . ?
C30 C29 H29A 109.3 . . ?
C23 C29 H29A 109.3 . . ?
C30 C29 H29B 109.3 . . ?
C23 C29 H29B 109.3 . . ?
H29A C29 H29B 107.9 . . ?
C32 C30 C29 109.68(17) . . ?
C32 C30 C31 109.89(18) . . ?
C29 C30 C31 110.05(17) . . ?
C32 C30 H30 109.1 . . ?
C29 C30 H30 109.1 . . ?
C31 C30 H30 109.1 . . ?
C30 C31 C25 109.43(16) . . ?
C30 C31 H31A 109.8 . . ?
C25 C31 H31A 109.8 . . ?
C30 C31 H31B 109.8 . . ?
C25 C31 H31B 109.8 . . ?
H31A C31 H31B 108.2 . . ?
C30 C32 C27 108.02(16) . . ?
C30 C32 H32A 110.1 . . ?
C27 C32 H32A 110.1 . . ?
C30 C32 H32B 110.1 . . ?
C27 C32 H32B 110.1 . . ?
H32A C32 H32B 108.4 . . ?
C38 C33 C34 116.6(2) . . ?
C38 C33 C23 121.2(2) . . ?
C34 C33 C23 122.1(2) . . ?
O7 C34 C35 121.1(2) . . ?
O7 C34 C33 118.4(2) . . ?
C35 C34 C33 120.5(3) . . ?
C36 C35 C34 121.6(3) . . ?
C36 C35 H35 119.2 . . ?
C34 C35 H35 119.2 . . ?
C35 C36 C37 118.0(3) . . ?
C35 C36 H36 121.0 . . ?
C37 C36 H36 121.0 . . ?
C36 C37 C38 121.8(3) . . ?
C36 C37 N3 120.2(3) . . ?
C38 C37 N3 117.9(3) . . ?
C33 C38 C37 121.5(3) . . ?
C33 C38 H38 119.3 . . ?
C37 C38 H38 119.3 . . ?
C44 C39 C40 116.18(19) . . ?
C44 C39 C25 121.17(17) . . ?
C40 C39 C25 122.63(19) . . ?
O10 C40 C41 120.31(18) . . ?
O10 C40 C39 118.63(19) . . ?
C41 C40 C39 121.1(2) . . ?
C42 C41 C40 121.32(19) . . ?
C42 C41 H41 119.3 . . ?
C40 C41 H41 119.3 . . ?
C41 C42 C43 117.6(2) . . ?
C41 C42 H42 121.2 . . ?
C43 C42 H42 121.2 . . ?
C44 C43 C42 122.1(2) . . ?
C44 C43 N4 118.78(18) . . ?
C42 C43 N4 119.13(19) . . ?
C39 C44 C43 121.78(18) . . ?
C39 C44 H44 119.1 . . ?
C43 C44 H44 119.1 . . ?
O9 N3 O8 124.9(3) . . ?
O9 N3 C37 119.4(3) . . ?
O8 N3 C37 115.7(3) . . ?
O11 N4 O12 123.24(19) . . ?
O11 N4 C43 118.23(17) . . ?
O12 N4 C43 118.53(17) . . ?
C34 O7 H7 109.5 . . ?
C40 O10 H10 109.5 . . ?
O13 C45 C48 106.7(3) . . ?
O13 C45 H45A 110.4 . . ?
C48 C45 H45A 110.4 . . ?
O13 C45 H45B 110.4 . . ?
C48 C45 H45B 110.4 . . ?
H45A C45 H45B 108.6 . . ?
O13 C46 C47 105.5(3) . . ?
O13 C46 H46A 110.6 . . ?
C47 C46 H46A 110.6 . . ?
O13 C46 H46B 110.6 . . ?
C47 C46 H46B 110.6 . . ?
H46A C46 H46B 108.8 . . ?
C48 C47 C46 104.0(3) . . ?
C48 C47 H47A 111.0 . . ?
C46 C47 H47A 111.0 . . ?
C48 C47 H47B 111.0 . . ?
C46 C47 H47B 111.0 . . ?
H47A C47 H47B 109.0 . . ?
C45 C48 C47 108.0(3) . . ?
C45 C48 H48A 110.1 . . ?
C47 C48 H48A 110.1 . . ?
C45 C48 H48B 110.1 . . ?
C47 C48 H48B 110.1 . . ?
H48A C48 H48B 108.4 . . ?
C46 O13 C45 110.6(2) . . ?
O14 C49 C52 106.33(18) . . ?
O14 C49 H49A 110.5 . . ?
C52 C49 H49A 110.5 . . ?
O14 C49 H49B 110.5 . . ?
C52 C49 H49B 110.5 . . ?
H49A C49 H49B 108.7 . . ?
O14 C50 C51 104.91(18) . . ?
O14 C50 H50A 110.8 . . ?
C51 C50 H50A 110.8 . . ?
O14 C50 H50B 110.8 . . ?
C51 C50 H50B 110.8 . . ?
H50A C50 H50B 108.8 . . ?
C50 C51 C52 102.1(2) . . ?
C50 C51 H51A 111.4 . . ?
C52 C51 H51A 111.4 . . ?
C50 C51 H51B 111.4 . . ?
C52 C51 H51B 111.4 . . ?
H51A C51 H51B 109.2 . . ?
C49 C52 C51 104.29(18) . . ?
C49 C52 H52A 110.9 . . ?
C51 C52 H52A 110.9 . . ?
C49 C52 H52B 110.9 . . ?
C51 C52 H52B 110.9 . . ?
H52A C52 H52B 108.9 . . ?
C50 O14 C49 109.75(16) . . ?
O15 C53 C56 106.7(3) . . ?
O15 C53 H53A 110.4 . . ?
C56 C53 H53A 110.4 . . ?
O15 C53 H53B 110.4 . . ?
C56 C53 H53B 110.4 . . ?
H53A C53 H53B 108.6 . . ?
O15 C54 C55 106.8(3) . . ?
O15 C54 H54A 110.4 . . ?
C55 C54 H54A 110.4 . . ?
O15 C54 H54B 110.4 . . ?
C55 C54 H54B 110.4 . . ?
H54A C54 H54B 108.6 . . ?
C54 C55 C56 99.7(3) . . ?
C54 C55 H55A 111.8 . . ?
C56 C55 H55A 111.8 . . ?
C54 C55 H55B 111.8 . . ?
C56 C55 H55B 111.8 . . ?
H55A C55 H55B 109.6 . . ?
C53 C56 C55 106.4(3) . . ?
C53 C56 H56A 110.5 . . ?
C55 C56 H56A 110.5 . . ?
C53 C56 H56B 110.5 . . ?
C55 C56 H56B 110.5 . . ?
H56A C56 H56B 108.6 . . ?
C54 O15 C53 109.8(3) . . ?
O15B C53B C56B 107.4(16) . . ?
O15B C53B H53C 110.2 . . ?
C56B C53B H53C 110.2 . . ?
O15B C53B H53D 110.2 . . ?
C56B C53B H53D 110.2 . . ?
H53C C53B H53D 108.5 . . ?
O15B C54B C55B 101.4(19) . . ?
O15B C54B H54C 111.5 . . ?
C55B C54B H54C 111.5 . . ?
O15B C54B H54D 111.5 . . ?
C55B C54B H54D 111.5 . . ?
H54C C54B H54D 109.3 . . ?
C54B C55B C56B 96.1(16) . . ?
C54B C55B H55C 112.5 . . ?
C56B C55B H55C 112.5 . . ?
C54B C55B H55D 112.5 . . ?
C56B C55B H55D 112.5 . . ?
H55C C55B H55D 110.1 . . ?
C53B C56B C55B 103.2(16) . . ?
C53B C56B H56C 111.1 . . ?
C55B C56B H56C 111.1 . . ?
C53B C56B H56D 111.1 . . ?
C55B C56B H56D 111.1 . . ?
H56C C56B H56D 109.1 . . ?
C53B O15B C54B 98.2(16) . . ?
O16 C57 C60 106.2(4) . . ?
O16 C57 H57A 110.5 . . ?
C60 C57 H57A 110.5 . . ?
O16 C57 H57B 110.5 . . ?
C60 C57 H57B 110.5 . . ?
H57A C57 H57B 108.7 . . ?
O16 C58 C59 106.2(5) . . ?
O16 C58 H58A 110.5 . . ?
C59 C58 H58A 110.5 . . ?
O16 C58 H58B 110.5 . . ?
C59 C58 H58B 110.5 . . ?
H58A C58 H58B 108.7 . . ?
C58 C59 C60 104.7(5) . . ?
C58 C59 H59A 110.8 . . ?
C60 C59 H59A 110.8 . . ?
C58 C59 H59B 110.8 . . ?
C60 C59 H59B 110.8 . . ?
H59A C59 H59B 108.9 . . ?
C59 C60 C57 102.0(5) . . ?
C59 C60 H60A 111.4 . . ?
C57 C60 H60A 111.4 . . ?
C59 C60 H60B 111.4 . . ?
C57 C60 H60B 111.4 . . ?
H60A C60 H60B 109.2 . . ?
C58 O16 C57 107.2(4) . . ?
O16B C57B C60B 120.9(14) . . ?
O16B C57B H57C 107.1 . . ?
C60B C57B H57C 107.1 . . ?
O16B C57B H57D 107.1 . . ?
C60B C57B H57D 107.1 . . ?
H57C C57B H57D 106.8 . . ?
C59B C58B O16B 110.7(15) . . ?
C59B C58B H58C 109.5 . . ?
O16B C58B H58C 109.5 . . ?
C59B C58B H58D 109.5 . . ?
O16B C58B H58D 109.5 . . ?
H58C C58B H58D 108.1 . . ?
C58B C59B C60B 108.3(14) . . ?
C58B C59B H59C 110.0 . . ?
C60B C59B H59C 110.0 . . ?
C58B C59B H59D 110.0 . . ?
C60B C59B H59D 110.0 . . ?
H59C C59B H59D 108.4 . . ?
C57B C60B C59B 99.2(13) . . ?
C57B C60B H60C 111.9 . . ?
C59B C60B H60C 111.9 . . ?
C57B C60B H60D 111.9 . . ?
C59B C60B H60D 111.9 . . ?
H60C C60B H60D 109.6 . . ?
C57B O16B C58B 99.3(12) . . ?
O17 C61 C64 107.3(3) . . ?
O17 C61 H61A 110.2 . . ?
C64 C61 H61A 110.2 . . ?
O17 C61 H61B 110.2 . . ?
C64 C61 H61B 110.2 . . ?
H61A C61 H61B 108.5 . . ?
O17 C62 C63 104.6(3) . . ?
O17 C62 H62A 110.8 . . ?
C63 C62 H62A 110.8 . . ?
O17 C62 H62B 110.8 . . ?
C63 C62 H62B 110.8 . . ?
H62A C62 H62B 108.9 . . ?
C64 C63 C62 104.5(3) . . ?
C64 C63 H63A 110.8 . . ?
C62 C63 H63A 110.8 . . ?
C64 C63 H63B 110.8 . . ?
C62 C63 H63B 110.8 . . ?
H63A C63 H63B 108.9 . . ?
C61 C64 C63 106.6(3) . . ?
C61 C64 H64A 110.4 . . ?
C63 C64 H64A 110.4 . . ?
C61 C64 H64B 110.4 . . ?
C63 C64 H64B 110.4 . . ?
H64A C64 H64B 108.6 . . ?
C61 O17 C62 109.4(2) . . ?
O17B C61B C64B 94.5(14) . . ?
O17B C61B H61C 112.8 . . ?
C64B C61B H61C 112.8 . . ?
O17B C61B H61D 112.8 . . ?
C64B C61B H61D 112.8 . . ?
H61C C61B H61D 110.3 . . ?
O17B C62B C63B 100.4(15) . . ?
O17B C62B H62C 111.7 . . ?
C63B C62B H62C 111.7 . . ?
O17B C62B H62D 111.7 . . ?
C63B C62B H62D 111.7 . . ?
H62C C62B H62D 109.5 . . ?
C64B C63B C62B 97.2(14) . . ?
C64B C63B H63C 112.3 . . ?
C62B C63B H63C 112.3 . . ?
C64B C63B H63D 112.3 . . ?
C62B C63B H63D 112.3 . . ?
H63C C63B H63D 109.9 . . ?
C61B C64B C63B 111.2(14) . . ?
C61B C64B H64C 109.4 . . ?
C63B C64B H64C 109.4 . . ?
C61B C64B H64D 109.4 . . ?
C63B C64B H64D 109.4 . . ?
H64C C64B H64D 108.0 . . ?
C62B O17B C61B 104.7(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
C11 C1 C2 C3 179.88(16) . . . . ?
C6 C1 C2 C3 58.6(2) . . . . ?
C7 C1 C2 C3 -58.1(2) . . . . ?
C1 C2 C3 C17 179.79(16) . . . . ?
C1 C2 C3 C4 -58.8(2) . . . . ?
C1 C2 C3 C9 58.0(2) . . . . ?
C17 C3 C4 C5 178.76(16) . . . . ?
C9 C3 C4 C5 -59.7(2) . . . . ?
C2 C3 C4 C5 57.6(2) . . . . ?
C3 C4 C5 C10 62.3(2) . . . . ?
C3 C4 C5 C6 -58.3(2) . . . . ?
C4 C5 C6 C1 61.1(2) . . . . ?
C10 C5 C6 C1 -59.6(2) . . . . ?
C11 C1 C6 C5 179.94(15) . . . . ?
C7 C1 C6 C5 57.91(19) . . . . ?
C2 C1 C6 C5 -60.2(2) . . . . ?
C11 C1 C7 C8 179.27(17) . . . . ?
C6 C1 C7 C8 -58.3(2) . . . . ?
C2 C1 C7 C8 58.1(2) . . . . ?
C1 C7 C8 C10 61.6(2) . . . . ?
C1 C7 C8 C9 -59.2(2) . . . . ?
C10 C8 C9 C3 -60.3(2) . . . . ?
C7 C8 C9 C3 60.9(2) . . . . ?
C17 C3 C9 C8 179.78(18) . . . . ?
C4 C3 C9 C8 59.2(2) . . . . ?
C2 C3 C9 C8 -59.6(2) . . . . ?
C9 C8 C10 C5 59.4(2) . . . . ?
C7 C8 C10 C5 -61.1(2) . . . . ?
C4 C5 C10 C8 -60.9(2) . . . . ?
C6 C5 C10 C8 59.6(2) . . . . ?
C6 C1 C11 C16 2.6(2) . . . . ?
C7 C1 C11 C16 122.8(2) . . . . ?
C2 C1 C11 C16 -115.9(2) . . . . ?
C6 C1 C11 C12 -176.38(17) . . . . ?
C7 C1 C11 C12 -56.3(2) . . . . ?
C2 C1 C11 C12 65.1(2) . . . . ?
C16 C11 C12 O1 -179.86(19) . . . . ?
C1 C11 C12 O1 -0.8(3) . . . . ?
C16 C11 C12 C13 0.3(3) . . . . ?
C1 C11 C12 C13 179.4(2) . . . . ?
O1 C12 C13 C14 -179.3(2) . . . . ?
C11 C12 C13 C14 0.5(4) . . . . ?
C12 C13 C14 C15 -0.7(3) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C13 C14 C15 N1 178.8(2) . . . . ?
C12 C11 C16 C15 -0.9(3) . . . . ?
C1 C11 C16 C15 -179.98(17) . . . . ?
C14 C15 C16 C11 0.8(3) . . . . ?
N1 C15 C16 C11 -177.96(17) . . . . ?
C4 C3 C17 C22 118.5(2) . . . . ?
C9 C3 C17 C22 -0.3(3) . . . . ?
C2 C3 C17 C22 -119.9(2) . . . . ?
C4 C3 C17 C18 -61.8(2) . . . . ?
C9 C3 C17 C18 179.41(19) . . . . ?
C2 C3 C17 C18 59.8(3) . . . . ?
C22 C17 C18 O4 -178.04(19) . . . . ?
C3 C17 C18 O4 2.2(3) . . . . ?
C22 C17 C18 C19 0.6(3) . . . . ?
C3 C17 C18 C19 -179.1(2) . . . . ?
O4 C18 C19 C20 178.1(2) . . . . ?
C17 C18 C19 C20 -0.6(3) . . . . ?
C18 C19 C20 C21 -0.2(3) . . . . ?
C19 C20 C21 C22 1.0(3) . . . . ?
C19 C20 C21 N2 -179.9(2) . . . . ?
C18 C17 C22 C21 0.2(3) . . . . ?
C3 C17 C22 C21 179.91(19) . . . . ?
C20 C21 C22 C17 -1.0(4) . . . . ?
N2 C21 C22 C17 179.9(2) . . . . ?
C14 C15 N1 O3 172.32(19) . . . . ?
C16 C15 N1 O3 -8.9(3) . . . . ?
C14 C15 N1 O2 -8.9(3) . . . . ?
C16 C15 N1 O2 169.88(17) . . . . ?
C20 C21 N2 O6 -171.1(2) . . . . ?
C22 C21 N2 O6 8.0(3) . . . . ?
C20 C21 N2 O5 10.1(3) . . . . ?
C22 C21 N2 O5 -170.8(2) . . . . ?
C33 C23 C24 C25 179.11(16) . . . . ?
C29 C23 C24 C25 -58.1(2) . . . . ?
C28 C23 C24 C25 57.7(2) . . . . ?
C23 C24 C25 C39 -179.05(15) . . . . ?
C23 C24 C25 C31 58.6(2) . . . . ?
C23 C24 C25 C26 -58.0(2) . . . . ?
C39 C25 C26 C27 179.61(17) . . . . ?
C31 C25 C26 C27 -59.7(2) . . . . ?
C24 C25 C26 C27 59.2(2) . . . . ?
C25 C26 C27 C28 -60.8(2) . . . . ?
C25 C26 C27 C32 60.7(2) . . . . ?
C32 C27 C28 C23 -61.7(2) . . . . ?
C26 C27 C28 C23 59.2(2) . . . . ?
C33 C23 C28 C27 -179.71(17) . . . . ?
C29 C23 C28 C27 58.2(2) . . . . ?
C24 C23 C28 C27 -57.5(2) . . . . ?
C33 C23 C29 C30 -178.52(16) . . . . ?
C28 C23 C29 C30 -57.9(2) . . . . ?
C24 C23 C29 C30 59.4(2) . . . . ?
C23 C29 C30 C32 60.2(2) . . . . ?
C23 C29 C30 C31 -60.8(2) . . . . ?
C32 C30 C31 C25 -63.1(2) . . . . ?
C29 C30 C31 C25 57.8(2) . . . . ?
C39 C25 C31 C30 -178.88(17) . . . . ?
C24 C25 C31 C30 -57.0(2) . . . . ?
C26 C25 C31 C30 60.3(2) . . . . ?
C29 C30 C32 C27 -59.6(2) . . . . ?
C31 C30 C32 C27 61.5(2) . . . . ?
C28 C27 C32 C30 61.2(2) . . . . ?
C26 C27 C32 C30 -59.8(2) . . . . ?
C29 C23 C33 C38 3.3(3) . . . . ?
C28 C23 C33 C38 -115.8(2) . . . . ?
C24 C23 C33 C38 123.0(2) . . . . ?
C29 C23 C33 C34 -178.91(17) . . . . ?
C28 C23 C33 C34 62.0(2) . . . . ?
C24 C23 C33 C34 -59.2(2) . . . . ?
C38 C33 C34 O7 -179.80(19) . . . . ?
C23 C33 C34 O7 2.3(3) . . . . ?
C38 C33 C34 C35 1.0(3) . . . . ?
C23 C33 C34 C35 -176.86(19) . . . . ?
O7 C34 C35 C36 -179.1(2) . . . . ?
C33 C34 C35 C36 0.0(3) . . . . ?
C34 C35 C36 C37 -1.1(4) . . . . ?
C35 C36 C37 C38 1.2(4) . . . . ?
C35 C36 C37 N3 -177.7(2) . . . . ?
C34 C33 C38 C37 -1.0(3) . . . . ?
C23 C33 C38 C37 176.95(19) . . . . ?
C36 C37 C38 C33 -0.1(3) . . . . ?
N3 C37 C38 C33 178.8(2) . . . . ?
C31 C25 C39 C44 -123.6(2) . . . . ?
C24 C25 C39 C44 114.2(2) . . . . ?
C26 C25 C39 C44 -5.2(3) . . . . ?
C31 C25 C39 C40 58.3(3) . . . . ?
C24 C25 C39 C40 -63.9(2) . . . . ?
C26 C25 C39 C40 176.76(18) . . . . ?
C44 C39 C40 O10 -178.63(18) . . . . ?
C25 C39 C40 O10 -0.5(3) . . . . ?
C44 C39 C40 C41 1.0(3) . . . . ?
C25 C39 C40 C41 179.14(18) . . . . ?
O10 C40 C41 C42 178.39(19) . . . . ?
C39 C40 C41 C42 -1.2(3) . . . . ?
C40 C41 C42 C43 0.9(3) . . . . ?
C41 C42 C43 C44 -0.5(3) . . . . ?
C41 C42 C43 N4 -179.98(19) . . . . ?
C40 C39 C44 C43 -0.5(3) . . . . ?
C25 C39 C44 C43 -178.74(18) . . . . ?
C42 C43 C44 C39 0.3(3) . . . . ?
N4 C43 C44 C39 179.81(18) . . . . ?
C36 C37 N3 O9 170.6(3) . . . . ?
C38 C37 N3 O9 -8.3(3) . . . . ?
C36 C37 N3 O8 -7.6(4) . . . . ?
C38 C37 N3 O8 173.5(2) . . . . ?
C44 C43 N4 O11 -177.87(18) . . . . ?
C42 C43 N4 O11 1.6(3) . . . . ?
C44 C43 N4 O12 1.8(3) . . . . ?
C42 C43 N4 O12 -178.72(19) . . . . ?
O13 C46 C47 C48 -21.4(5) . . . . ?
O13 C45 C48 C47 0.7(8) . . . . ?
C46 C47 C48 C45 12.6(7) . . . . ?
C47 C46 O13 C45 23.2(5) . . . . ?
C48 C45 O13 C46 -15.2(6) . . . . ?
O14 C50 C51 C52 -35.3(2) . . . . ?
O14 C49 C52 C51 -16.6(3) . . . . ?
C50 C51 C52 C49 31.3(3) . . . . ?
C51 C50 O14 C49 26.3(3) . . . . ?
C52 C49 O14 C50 -5.9(3) . . . . ?
O15 C54 C55 C56 32.2(5) . . . . ?
O15 C53 C56 C55 10.9(7) . . . . ?
C54 C55 C56 C53 -25.8(6) . . . . ?
C55 C54 O15 C53 -28.1(5) . . . . ?
C56 C53 O15 C54 10.2(7) . . . . ?
O15B C54B C55B C56B 49(3) . . . . ?
O15B C53B C56B C55B -12(4) . . . . ?
C54B C55B C56B C53B -22(4) . . . . ?
C56B C53B O15B C54B 43(3) . . . . ?
C55B C54B O15B C53B -58(2) . . . . ?
O16 C58 C59 C60 -29.9(8) . . . . ?
C58 C59 C60 C57 37.3(7) . . . . ?
O16 C57 C60 C59 -31.0(6) . . . . ?
C59 C58 O16 C57 10.2(8) . . . . ?
C60 C57 O16 C58 13.3(7) . . . . ?
O16B C58B C59B C60B 8(3) . . . . ?
O16B C57B C60B C59B -9(3) . . . . ?
C58B C59B C60B C57B 0(3) . . . . ?
C60B C57B O16B C58B 13(3) . . . . ?
C59B C58B O16B C57B -12(2) . . . . ?
O17 C62 C63 C64 25.9(4) . . . . ?
O17 C61 C64 C63 -0.4(5) . . . . ?
C62 C63 C64 C61 -15.6(5) . . . . ?
C64 C61 O17 C62 17.7(5) . . . . ?
C63 C62 O17 C61 -27.4(4) . . . . ?
O17B C62B C63B C64B 36(3) . . . . ?
O17B C61B C64B C63B -26(3) . . . . ?
C62B C63B C64B C61B -5(3) . . . . ?
C63B C62B O17B C61B -58(2) . . . . ?
C64B C61B O17B C62B 51(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O15^a 0.78 1.94 2.701(3) 165.4 . yes
O4 H4 O17^a 0.89 1.81 2.689(2) 173.0 . yes
O7 H7 O13 0.73 1.92 2.649(3) 173.1 . yes
O10 H10 O14 0.85 1.81 2.656(2) 174.4 . yes

_refine_diff_density_max         0.649
_refine_diff_density_min         -0.562
_refine_diff_density_rms         0.152

####################################################################### 
# 
# 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 2455714'
loop_
_audit_author_name
_audit_author_address
'Masatoshi Kawahata'
;Showa Pharmaceutical University
Japan
;
_audit_update_record             
;
2025-06-02 deposited with the CCDC.	2025-10-13 downloaded from the CCDC.
;

# start vrf
_vrf_PLAT029_1c                  
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low . 0.920
RESPONSE: This is attibuted to low crystallinity and weak diffractions.
Although repeated crystallization and diffraction experiments were 
perfomed, this structure represents the best of all.
;
_vrf_PLAT911_1c                  
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L= 0.600  328
RESPONSE: This is attibuted to low crystallinity and weak diffractions.
Although repeated crystallization and diffraction experiments were 
perfomed, this structure represents the best of all.
;
# end vrf

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H28 N2 O8'
_chemical_formula_weight         496.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   7.0389(14)
_cell_length_b                   10.510(2)
_cell_length_c                   15.782(3)
_cell_angle_alpha                91.671(4)
_cell_angle_beta                 90.864(4)
_cell_angle_gamma                100.318(4)
_cell_volume                     1147.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9919
_cell_measurement_theta_min      6.93
_cell_measurement_theta_max      79.35

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_F_000             524
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.894
_shelx_estimated_absorpt_T_min   0.841
_shelx_estimated_absorpt_T_max   0.916
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7710
_exptl_absorpt_correction_T_max  0.8895
_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            12482
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         6.931
_diffrn_reflns_theta_max         80.016
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.872
_diffrn_measured_fraction_theta_full 0.920
_diffrn_reflns_Laue_measured_fraction_max 0.872
_diffrn_reflns_Laue_measured_fraction_full 0.920
_diffrn_reflns_point_group_measured_fraction_max 0.872
_diffrn_reflns_point_group_measured_fraction_full 0.920
_reflns_number_total             4364
_reflns_number_gt                4309
_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-2019/3 (Sheldrick, 2019)'
_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)+(0.0396P)²+0.6229P] 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         4364
_refine_ls_number_parameters     331
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1120
_refine_ls_wR_factor_gt          0.1118
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_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 0.37655(17) 0.47477(11) 0.75412(8) 0.0143(2) Uani 1 1 d . . . . .
C2 C 0.40365(19) 0.57829(12) 0.82630(8) 0.0175(3) Uani 1 1 d . . . . .
H2A H 0.397965 0.663847 0.802766 0.021 Uiso 1 1 calc R U . . .
H2B H 0.532257 0.582920 0.853712 0.021 Uiso 1 1 calc R U . . .
C3 C 0.2459(2) 0.54618(12) 0.89266(9) 0.0208(3) Uani 1 1 d . . . . .
H3 H 0.267565 0.614173 0.939188 0.025 Uiso 1 1 calc R U . . .
C4 C 0.25544(19) 0.41414(12) 0.92998(8) 0.0188(3) Uani 1 1 d . . . . .
H4A H 0.154722 0.394061 0.973123 0.023 Uiso 1 1 calc R U . . .
H4B H 0.382902 0.417143 0.958112 0.023 Uiso 1 1 calc R U . . .
C5 C 0.22460(17) 0.30787(11) 0.85973(8) 0.0145(3) Uani 1 1 d . . . . .
C6 C 0.38585(17) 0.34248(11) 0.79372(8) 0.0134(2) Uani 1 1 d . . . . .
H6A H 0.513671 0.346234 0.821685 0.016 Uiso 1 1 calc R U . . .
H6B H 0.370640 0.274135 0.748361 0.016 Uiso 1 1 calc R U . . .
C7 C 0.17404(18) 0.47138(12) 0.71329(8) 0.0180(3) Uani 1 1 d . . . . .
H7A H 0.167864 0.556282 0.688859 0.022 Uiso 1 1 calc R U . . .
H7B H 0.151408 0.404800 0.666794 0.022 Uiso 1 1 calc R U . . .
C8 C 0.01671(18) 0.44039(12) 0.77984(9) 0.0201(3) Uani 1 1 d . . . . .
H8 H -0.112865 0.437754 0.752281 0.024 Uiso 1 1 calc R U . . .
C9 C 0.02524(18) 0.30837(12) 0.81694(9) 0.0180(3) Uani 1 1 d . . . . .
H9A H 0.001386 0.240676 0.771149 0.022 Uiso 1 1 calc R U . . .
H9B H -0.077325 0.287919 0.859225 0.022 Uiso 1 1 calc R U . . .
C10 C 0.0472(2) 0.54388(13) 0.85086(10) 0.0243(3) Uani 1 1 d . . . . .
H10A H -0.055072 0.524201 0.893340 0.029 Uiso 1 1 calc R U . . .
H10B H 0.040767 0.629493 0.827581 0.029 Uiso 1 1 calc R U . . .
C11 C 0.53155(17) 0.50571(11) 0.68673(8) 0.0139(2) Uani 1 1 d . . . . .
C12 C 0.53921(18) 0.42435(11) 0.61415(8) 0.0158(3) Uani 1 1 d . . . . .
C13 C 0.68276(19) 0.45458(12) 0.55328(8) 0.0184(3) Uani 1 1 d . . . . .
H13 H 0.684677 0.397944 0.505398 0.022 Uiso 1 1 calc R U . . .
C14 C 0.82081(18) 0.56542(12) 0.56221(8) 0.0179(3) Uani 1 1 d . . . . .
H14 H 0.917885 0.586383 0.521173 0.022 Uiso 1 1 calc R U . . .
C15 C 0.81309(17) 0.64501(11) 0.63295(8) 0.0153(3) Uani 1 1 d . . . . .
C16 C 0.67165(17) 0.61739(11) 0.69379(8) 0.0143(2) Uani 1 1 d . . . . .
H16 H 0.670771 0.675699 0.740866 0.017 Uiso 1 1 calc R U . . .
C17 C 0.23019(17) 0.17431(11) 0.89529(8) 0.0147(3) Uani 1 1 d . . . . .
C18 C 0.19379(17) 0.05990(12) 0.84359(8) 0.0153(3) Uani 1 1 d . . . . .
C19 C 0.19146(18) -0.06140(12) 0.87789(8) 0.0185(3) Uani 1 1 d . . . . .
H19 H 0.163063 -0.136786 0.841988 0.022 Uiso 1 1 calc R U . . .
C20 C 0.22980(18) -0.07374(12) 0.96333(9) 0.0185(3) Uani 1 1 d . . . . .
H20 H 0.228565 -0.156239 0.986589 0.022 Uiso 1 1 calc R U . . .
C21 C 0.26981(18) 0.03788(12) 1.01341(8) 0.0169(3) Uani 1 1 d . . . . .
C22 C 0.26877(17) 0.15927(12) 0.98090(8) 0.0165(3) Uani 1 1 d . . . . .
H22 H 0.294943 0.233573 1.017848 0.020 Uiso 1 1 calc R U . . .
C23 C 0.39640(19) 0.08497(13) 0.42979(8) 0.0193(3) Uani 1 1 d . . . . .
C24 C 0.4649(2) 0.01296(14) 0.35631(9) 0.0228(3) Uani 1 1 d . . . . .
H24A H 0.577250 -0.026128 0.373039 0.027 Uiso 1 1 calc R U . . .
H24B H 0.501308 0.070864 0.308581 0.027 Uiso 1 1 calc R U . . .
C25 C 0.2914(2) -0.09072(14) 0.33250(9) 0.0263(3) Uani 1 1 d . . . . .
H25A H 0.219054 -0.064949 0.283524 0.032 Uiso 1 1 calc R U . . .
H25B H 0.331685 -0.174215 0.318294 0.032 Uiso 1 1 calc R U . . .
C26 C 0.1704(2) -0.10034(15) 0.41153(10) 0.0314(3) Uani 1 1 d . . . . .
H26A H 0.031216 -0.113595 0.396213 0.038 Uiso 1 1 calc R U . . .
H26B H 0.194442 -0.173470 0.445820 0.038 Uiso 1 1 calc R U . . .
N1 N 0.95880(15) 0.76058(10) 0.64473(7) 0.0170(2) Uani 1 1 d . . . . .
N2 N 0.31729(16) 0.02835(11) 1.10322(7) 0.0202(2) Uani 1 1 d . . . . .
O1 O 0.40380(13) 0.31639(9) 0.60387(6) 0.0197(2) Uani 1 1 d . . . . .
H1 H 0.427(3) 0.2765(18) 0.5551(12) 0.030 Uiso 1 1 d . U . . .
O2 O 1.09648(15) 0.77883(10) 0.59747(7) 0.0305(3) Uani 1 1 d . . . . .
O3 O 0.93902(15) 0.83687(9) 0.70385(6) 0.0274(2) Uani 1 1 d . . . . .
O4 O 0.16216(13) 0.06933(9) 0.75914(6) 0.0183(2) Uani 1 1 d . . . . .
H4 H 0.121(3) -0.0075(19) 0.7386(12) 0.027 Uiso 1 1 d . U . . .
O5 O 0.33575(15) -0.07826(10) 1.12921(6) 0.0271(2) Uani 1 1 d . . . . .
O6 O 0.33985(17) 0.12678(10) 1.14878(6) 0.0300(3) Uani 1 1 d . . . . .
O7 O 0.47535(16) 0.18662(10) 0.46290(7) 0.0289(2) Uani 1 1 d . . . . .
O8 O 0.22996(14) 0.02248(10) 0.45871(6) 0.0266(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 1.5347(17) . ?
C1 C2 1.5377(16) . ?
C1 C7 1.5496(17) . ?
C1 C6 1.5524(16) . ?
C2 C3 1.5378(18) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C10 1.533(2) . ?
C3 C4 1.5351(18) . ?
C3 H3 1.0000 . ?
C4 C5 1.5354(17) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C17 1.5336(16) . ?
C5 C9 1.5490(17) . ?
C5 C6 1.5542(16) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.5367(18) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C10 1.5243(19) . ?
C8 C9 1.5323(17) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C16 1.3918(17) . ?
C11 C12 1.4168(17) . ?
C12 O1 1.3489(15) . ?
C12 C13 1.4060(18) . ?
C13 C14 1.3791(18) . ?
C13 H13 0.9500 . ?
C14 C15 1.3830(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.3925(17) . ?
C15 N1 1.4480(16) . ?
C16 H16 0.9500 . ?
C17 C22 1.3931(18) . ?
C17 C18 1.4154(17) . ?
C18 O4 1.3573(15) . ?
C18 C19 1.3970(17) . ?
C19 C20 1.3854(19) . ?
C19 H19 0.9500 . ?
C20 C21 1.3788(18) . ?
C20 H20 0.9500 . ?
C21 C22 1.3901(18) . ?
C21 N2 1.4617(17) . ?
C22 H22 0.9500 . ?
C23 O7 1.2121(17) . ?
C23 O8 1.3305(17) . ?
C23 C24 1.4988(18) . ?
C24 C25 1.5183(19) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.517(2) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 O8 1.4618(18) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
N1 O2 1.2231(15) . ?
N1 O3 1.2381(15) . ?
N2 O6 1.2275(15) . ?
N2 O5 1.2320(15) . ?
O1 H1 0.90(2) . ?
O4 H4 0.86(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 C1 C2 111.53(10) . . ?
C11 C1 C7 109.62(10) . . ?
C2 C1 C7 107.53(10) . . ?
C11 C1 C6 110.54(9) . . ?
C2 C1 C6 107.80(10) . . ?
C7 C1 C6 109.74(9) . . ?
C1 C2 C3 110.70(10) . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C10 C3 C4 110.11(11) . . ?
C10 C3 C2 109.47(11) . . ?
C4 C3 C2 109.70(10) . . ?
C10 C3 H3 109.2 . . ?
C4 C3 H3 109.2 . . ?
C2 C3 H3 109.2 . . ?
C3 C4 C5 110.34(10) . . ?
C3 C4 H4A 109.6 . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
C5 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C17 C5 C4 111.57(10) . . ?
C17 C5 C9 109.93(10) . . ?
C4 C5 C9 107.61(10) . . ?
C17 C5 C6 110.26(9) . . ?
C4 C5 C6 107.99(10) . . ?
C9 C5 C6 109.41(10) . . ?
C1 C6 C5 110.95(9) . . ?
C1 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
C1 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 C1 110.40(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 109.36(11) . . ?
C10 C8 C7 110.12(11) . . ?
C9 C8 C7 109.49(10) . . ?
C10 C8 H8 109.3 . . ?
C9 C8 H8 109.3 . . ?
C7 C8 H8 109.3 . . ?
C8 C9 C5 110.99(10) . . ?
C8 C9 H9A 109.4 . . ?
C5 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C5 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C8 C10 C3 108.60(10) . . ?
C8 C10 H10A 110.0 . . ?
C3 C10 H10A 110.0 . . ?
C8 C10 H10B 110.0 . . ?
C3 C10 H10B 110.0 . . ?
H10A C10 H10B 108.4 . . ?
C16 C11 C12 116.49(11) . . ?
C16 C11 C1 121.05(11) . . ?
C12 C11 C1 122.46(11) . . ?
O1 C12 C13 120.05(11) . . ?
O1 C12 C11 118.48(11) . . ?
C13 C12 C11 121.46(11) . . ?
C14 C13 C12 120.83(12) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 117.71(12) . . ?
C13 C14 H14 121.1 . . ?
C15 C14 H14 121.1 . . ?
C14 C15 C16 122.45(11) . . ?
C14 C15 N1 118.80(11) . . ?
C16 C15 N1 118.75(11) . . ?
C11 C16 C15 121.05(11) . . ?
C11 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C22 C17 C18 116.46(11) . . ?
C22 C17 C5 121.46(11) . . ?
C18 C17 C5 122.08(11) . . ?
O4 C18 C19 119.87(11) . . ?
O4 C18 C17 118.94(11) . . ?
C19 C18 C17 121.18(12) . . ?
C20 C19 C18 121.20(12) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C21 C20 C19 117.68(11) . . ?
C21 C20 H20 121.2 . . ?
C19 C20 H20 121.2 . . ?
C20 C21 C22 122.03(12) . . ?
C20 C21 N2 118.95(11) . . ?
C22 C21 N2 119.01(11) . . ?
C21 C22 C17 121.42(11) . . ?
C21 C22 H22 119.3 . . ?
C17 C22 H22 119.3 . . ?
O7 C23 O8 120.71(12) . . ?
O7 C23 C24 127.65(13) . . ?
O8 C23 C24 111.64(11) . . ?
C23 C24 C25 103.63(11) . . ?
C23 C24 H24A 111.0 . . ?
C25 C24 H24A 111.0 . . ?
C23 C24 H24B 111.0 . . ?
C25 C24 H24B 111.0 . . ?
H24A C24 H24B 109.0 . . ?
C26 C25 C24 103.82(11) . . ?
C26 C25 H25A 111.0 . . ?
C24 C25 H25A 111.0 . . ?
C26 C25 H25B 111.0 . . ?
C24 C25 H25B 111.0 . . ?
H25A C25 H25B 109.0 . . ?
O8 C26 C25 105.78(11) . . ?
O8 C26 H26A 110.6 . . ?
C25 C26 H26A 110.6 . . ?
O8 C26 H26B 110.6 . . ?
C25 C26 H26B 110.6 . . ?
H26A C26 H26B 108.7 . . ?
O2 N1 O3 122.54(11) . . ?
O2 N1 C15 119.66(11) . . ?
O3 N1 C15 117.80(10) . . ?
O6 N2 O5 123.15(11) . . ?
O6 N2 C21 118.71(11) . . ?
O5 N2 C21 118.12(11) . . ?
C12 O1 H1 107.7(12) . . ?
C18 O4 H4 107.6(12) . . ?
C23 O8 C26 110.19(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 179.47(10) . . . . ?
C7 C1 C2 C3 59.25(13) . . . . ?
C6 C1 C2 C3 -59.01(13) . . . . ?
C1 C2 C3 C10 -61.21(13) . . . . ?
C1 C2 C3 C4 59.72(14) . . . . ?
C10 C3 C4 C5 60.69(14) . . . . ?
C2 C3 C4 C5 -59.85(14) . . . . ?
C3 C4 C5 C17 -179.11(10) . . . . ?
C3 C4 C5 C9 -58.45(13) . . . . ?
C3 C4 C5 C6 59.56(13) . . . . ?
C11 C1 C6 C5 -177.94(9) . . . . ?
C2 C1 C6 C5 59.93(12) . . . . ?
C7 C1 C6 C5 -56.90(13) . . . . ?
C17 C5 C6 C1 177.49(9) . . . . ?
C4 C5 C6 C1 -60.38(12) . . . . ?
C9 C5 C6 C1 56.47(12) . . . . ?
C11 C1 C7 C8 179.95(9) . . . . ?
C2 C1 C7 C8 -58.63(13) . . . . ?
C6 C1 C7 C8 58.37(13) . . . . ?
C1 C7 C8 C10 60.50(13) . . . . ?
C1 C7 C8 C9 -59.78(13) . . . . ?
C10 C8 C9 C5 -60.85(13) . . . . ?
C7 C8 C9 C5 59.89(14) . . . . ?
C17 C5 C9 C8 -179.29(10) . . . . ?
C4 C5 C9 C8 59.02(13) . . . . ?
C6 C5 C9 C8 -58.07(13) . . . . ?
C9 C8 C10 C3 60.14(13) . . . . ?
C7 C8 C10 C3 -60.21(14) . . . . ?
C4 C3 C10 C8 -60.44(14) . . . . ?
C2 C3 C10 C8 60.23(13) . . . . ?
C2 C1 C11 C16 -1.41(15) . . . . ?
C7 C1 C11 C16 117.57(12) . . . . ?
C6 C1 C11 C16 -121.33(12) . . . . ?
C2 C1 C11 C12 179.36(11) . . . . ?
C7 C1 C11 C12 -61.67(14) . . . . ?
C6 C1 C11 C12 59.43(14) . . . . ?
C16 C11 C12 O1 -178.67(10) . . . . ?
C1 C11 C12 O1 0.60(17) . . . . ?
C16 C11 C12 C13 0.81(17) . . . . ?
C1 C11 C12 C13 -179.92(11) . . . . ?
O1 C12 C13 C14 179.14(11) . . . . ?
C11 C12 C13 C14 -0.33(19) . . . . ?
C12 C13 C14 C15 0.17(19) . . . . ?
C13 C14 C15 C16 -0.54(19) . . . . ?
C13 C14 C15 N1 178.71(11) . . . . ?
C12 C11 C16 C15 -1.16(17) . . . . ?
C1 C11 C16 C15 179.55(10) . . . . ?
C14 C15 C16 C11 1.08(19) . . . . ?
N1 C15 C16 C11 -178.17(10) . . . . ?
C4 C5 C17 C22 -2.91(16) . . . . ?
C9 C5 C17 C22 -122.21(12) . . . . ?
C6 C5 C17 C22 117.08(12) . . . . ?
C4 C5 C17 C18 176.12(11) . . . . ?
C9 C5 C17 C18 56.82(15) . . . . ?
C6 C5 C17 C18 -63.89(14) . . . . ?
C22 C17 C18 O4 -177.67(11) . . . . ?
C5 C17 C18 O4 3.25(17) . . . . ?
C22 C17 C18 C19 1.84(17) . . . . ?
C5 C17 C18 C19 -177.24(11) . . . . ?
O4 C18 C19 C20 177.75(11) . . . . ?
C17 C18 C19 C20 -1.75(19) . . . . ?
C18 C19 C20 C21 0.19(19) . . . . ?
C19 C20 C21 C22 1.22(19) . . . . ?
C19 C20 C21 N2 -177.94(11) . . . . ?
C20 C21 C22 C17 -1.10(19) . . . . ?
N2 C21 C22 C17 178.07(11) . . . . ?
C18 C17 C22 C21 -0.45(18) . . . . ?
C5 C17 C22 C21 178.63(11) . . . . ?
O7 C23 C24 C25 -169.19(14) . . . . ?
O8 C23 C24 C25 11.69(15) . . . . ?
C23 C24 C25 C26 -20.05(14) . . . . ?
C24 C25 C26 O8 21.93(15) . . . . ?
C14 C15 N1 O2 -7.66(17) . . . . ?
C16 C15 N1 O2 171.62(11) . . . . ?
C14 C15 N1 O3 173.20(11) . . . . ?
C16 C15 N1 O3 -7.52(17) . . . . ?
C20 C21 N2 O6 -175.09(12) . . . . ?
C22 C21 N2 O6 5.72(18) . . . . ?
C20 C21 N2 O5 6.05(17) . . . . ?
C22 C21 N2 O5 -173.15(11) . . . . ?
O7 C23 O8 C26 -176.76(13) . . . . ?
C24 C23 O8 C26 2.43(15) . . . . ?
C25 C26 O8 C23 -15.68(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O7 0.90(2) 1.78(2) 2.6770(14) 175.5(18) . yes
O4 H4 O3 0.86(2) 1.95(2) 2.7671(14) 159.1(17) 1_445 yes

_refine_diff_density_max         0.298
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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 2455713'
loop_
_audit_author_name
_audit_author_address
'Masatoshi Kawahata'
;Showa Pharmaceutical University
Japan
;
_audit_update_record             
;
2025-06-02 deposited with the CCDC.	2025-10-13 downloaded from the CCDC.
;

# start vrf
_vrf_PLAT029_1b                  
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low . 0.942
RESPONSE: This is attibuted to low crystallinity and weak diffractions.
Although repeated crystallization and diffraction experiments were 
perfomed, this structure represents the best of all.
;
# end vrf

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H30 N2 O8'
_chemical_formula_weight         498.52

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      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

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

_cell_length_a                   22.1125(19)
_cell_length_b                   6.6904(6)
_cell_length_c                   16.0518(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2374.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9802
_cell_measurement_theta_min      3.40
_cell_measurement_theta_max      79.09

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.865
_shelx_estimated_absorpt_T_min   0.903
_shelx_estimated_absorpt_T_max   0.918
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7881
_exptl_absorpt_correction_T_max  0.9288
_exptl_absorpt_process_details   'SADBS 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            27736
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.998
_diffrn_reflns_theta_max         79.852
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measured_fraction_theta_full 0.942
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_Laue_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_point_group_measured_fraction_full 0.942
_reflns_number_total             2593
_reflns_number_gt                2521
_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-2019/3 (Sheldrick, 2019)'
_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)+(0.0875P)²+3.7390P] 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         2593
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0689
_refine_ls_wR_factor_ref         0.1884
_refine_ls_wR_factor_gt          0.1876
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_restrained_S_all      1.149
_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 0.36808(12) 0.250000 0.94603(17) 0.0157(6) Uani 1 2 d S T P . .
C2 C 0.33201(12) 0.250000 0.86379(17) 0.0152(6) Uani 1 2 d S T P . .
H2A H 0.305634 0.369526 0.862345 0.018 Uiso 0.5 1 calc R U P . .
H2B H 0.305634 0.130474 0.862345 0.018 Uiso 0.5 1 calc R U P . .
C3 C 0.37272(12) 0.250000 0.78569(17) 0.0147(6) Uani 1 2 d S T P . .
C4 C 0.40815(9) 0.4388(4) 0.94678(12) 0.0190(5) Uani 1 1 d . . . . .
H4A H 0.382337 0.559642 0.945190 0.023 Uiso 1 1 calc R U . . .
H4B H 0.432325 0.442537 0.998662 0.023 Uiso 1 1 calc R U . . .
C5 C 0.45054(9) 0.4371(4) 0.87092(12) 0.0205(5) Uani 1 1 d . . . . .
H5 H 0.476926 0.558406 0.872400 0.025 Uiso 1 1 calc R U . . .
C6 C 0.41299(9) 0.4381(4) 0.79017(12) 0.0182(5) Uani 1 1 d . . . . .
H6A H 0.440393 0.441558 0.741425 0.022 Uiso 1 1 calc R U . . .
H6B H 0.387304 0.559254 0.788538 0.022 Uiso 1 1 calc R U . . .
C7 C 0.49002(13) 0.250000 0.87361(19) 0.0233(7) Uani 1 2 d S T P . .
H7A H 0.518047 0.249998 0.825509 0.028 Uiso 1 2 calc R U P . .
H7B H 0.514473 0.250003 0.925274 0.028 Uiso 1 2 calc R U P . .
C8 C 0.32449(13) 0.250000 1.02085(17) 0.0148(6) Uani 1 2 d S T P . .
C9 C 0.34549(13) 0.250000 1.10456(18) 0.0160(6) Uani 1 2 d S T P . .
C10 C 0.30486(14) 0.250000 1.17143(18) 0.0190(6) Uani 1 2 d S T P . .
H10 H 0.320095 0.250000 1.226762 0.023 Uiso 1 2 calc R U P . .
C11 C 0.24286(14) 0.250000 1.15863(19) 0.0188(6) Uani 1 2 d S T P . .
H11 H 0.215328 0.250000 1.204065 0.023 Uiso 1 2 calc R U P . .
C12 C 0.22270(13) 0.250000 1.07715(19) 0.0171(6) Uani 1 2 d S T P . .
C13 C 0.26220(13) 0.250000 1.01012(19) 0.0173(6) Uani 1 2 d S T P . .
H13 H 0.246177 0.250000 0.955207 0.021 Uiso 1 2 calc R U P . .
C14 C 0.33382(13) 0.250000 0.70642(18) 0.0147(6) Uani 1 2 d S T P . .
C15 C 0.35902(13) 0.250000 0.62534(18) 0.0147(6) Uani 1 2 d S T P . .
C16 C 0.32242(13) 0.250000 0.55453(18) 0.0172(6) Uani 1 2 d S T P . .
H16 H 0.340651 0.250000 0.500945 0.021 Uiso 1 2 calc R U P . .
C17 C 0.26008(13) 0.250000 0.56102(18) 0.0179(6) Uani 1 2 d S T P . .
H17 H 0.235097 0.250000 0.512872 0.022 Uiso 1 2 calc R U P . .
C18 C 0.23553(13) 0.250000 0.63985(18) 0.0159(6) Uani 1 2 d S T P . .
C19 C 0.27100(13) 0.250000 0.71114(18) 0.0164(6) Uani 1 2 d S T P . .
H19 H 0.252010 0.250000 0.764232 0.020 Uiso 1 2 calc R U P . .
C20 C 0.46674(10) 0.0747(4) 0.40679(14) 0.0239(5) Uani 1 1 d . . . . .
H20A H 0.458936 -0.046136 0.440722 0.029 Uiso 1 1 calc R U . . .
H20B H 0.509626 0.072297 0.389097 0.029 Uiso 1 1 calc R U . . .
C21 C 0.42662(11) 0.0737(4) 0.33161(14) 0.0287(5) Uani 1 1 d . . . . .
H21A H 0.435229 -0.046472 0.297619 0.034 Uiso 1 1 calc R U . . .
H21B H 0.383797 0.067670 0.349436 0.034 Uiso 1 1 calc R U . . .
N1 N 0.15771(11) 0.250000 1.06027(17) 0.0207(6) Uani 1 2 d S T P . .
N2 N 0.17006(11) 0.250000 0.64986(15) 0.0188(6) Uani 1 2 d S T P . .
O1 O 0.40570(9) 0.250000 1.11841(13) 0.0205(5) Uani 1 2 d S T P . .
H1 H 0.409(2) 0.226(13) 1.173(3) 0.031 Uiso 0.5 1 d . U P . .
O2 O 0.12302(10) 0.250000 1.12022(15) 0.0283(6) Uani 1 2 d S T P . .
O3 O 0.14031(10) 0.250000 0.98759(15) 0.0336(6) Uani 1 2 d S T P . .
O4 O 0.41990(9) 0.250000 0.61706(14) 0.0185(5) Uani 1 2 d S T P . .
H4 H 0.421(2) 0.292(9) 0.573(3) 0.028 Uiso 0.5 1 d . U P . .
O5 O 0.13865(10) 0.250000 0.58695(14) 0.0286(6) Uani 1 2 d S T P . .
O6 O 0.14897(10) 0.250000 0.72128(14) 0.0294(6) Uani 1 2 d S T P . .
O7 O 0.45555(10) 0.250000 0.45580(12) 0.0210(5) Uani 1 2 d S T P . .
O8 O 0.43621(12) 0.250000 0.28221(13) 0.0296(6) Uani 1 2 d S T 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 C8 1.540(4) . ?
C1 C2 1.542(4) . ?
C1 C4 1.543(3) . ?
C1 C4 1.543(3) 7_565 ?
C2 C3 1.543(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C14 1.536(4) . ?
C3 C6 1.543(3) . ?
C3 C6 1.543(3) 7_565 ?
C4 C5 1.537(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C7 1.527(3) . ?
C5 C6 1.539(3) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C13 1.388(4) . ?
C8 C9 1.422(4) . ?
C9 O1 1.350(3) . ?
C9 C10 1.400(4) . ?
C10 C11 1.386(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(4) . ?
C12 N1 1.462(4) . ?
C13 H13 0.9500 . ?
C14 C19 1.391(4) . ?
C14 C15 1.416(4) . ?
C15 O4 1.353(3) . ?
C15 C16 1.395(4) . ?
C16 C17 1.382(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.377(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.387(4) . ?
C18 N2 1.457(4) . ?
C19 H19 0.9500 . ?
C20 O7 1.434(3) . ?
C20 C21 1.498(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 O8 1.437(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
N1 O3 1.229(4) . ?
N1 O2 1.231(3) . ?
N2 O5 1.226(3) . ?
N2 O6 1.238(3) . ?
O1 H1 0.89(5) . ?
O1 H1 0.89(5) 7_565 ?
O4 H4 0.76(5) . ?
O4 H4 0.76(5) 7_565 ?

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
C8 C1 C2 110.1(2) . . ?
C8 C1 C4 110.69(15) . . ?
C2 C1 C4 107.67(15) . . ?
C8 C1 C4 110.70(15) . 7_565 ?
C2 C1 C4 107.67(15) . 7_565 ?
C4 C1 C4 109.9(2) . 7_565 ?
C1 C2 C3 113.2(2) . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
C3 C2 H2B 108.9 . . ?
H2A C2 H2B 107.8 . . ?
C14 C3 C2 110.3(2) . . ?
C14 C3 C6 111.20(15) . . ?
C2 C3 C6 107.38(15) . . ?
C14 C3 C6 111.20(15) . 7_565 ?
C2 C3 C6 107.38(15) . 7_565 ?
C6 C3 C6 109.3(2) . 7_565 ?
C5 C4 C1 109.76(19) . . ?
C5 C4 H4A 109.7 . . ?
C1 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
C1 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C7 C5 C4 109.4(2) . . ?
C7 C5 C6 109.6(2) . . ?
C4 C5 C6 109.76(16) . . ?
C7 C5 H5 109.3 . . ?
C4 C5 H5 109.3 . . ?
C6 C5 H5 109.3 . . ?
C5 C6 C3 110.29(19) . . ?
C5 C6 H6A 109.6 . . ?
C3 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
C3 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C5 C7 C5 110.1(2) 7_565 . ?
C5 C7 H7A 109.6 7_565 . ?
C5 C7 H7A 109.6 . . ?
C5 C7 H7B 109.6 7_565 . ?
C5 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C13 C8 C9 116.2(3) . . ?
C13 C8 C1 121.6(2) . . ?
C9 C8 C1 122.2(2) . . ?
O1 C9 C10 120.5(3) . . ?
O1 C9 C8 118.5(3) . . ?
C10 C9 C8 121.0(3) . . ?
C11 C10 C9 121.4(3) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C12 C11 C10 117.3(3) . . ?
C12 C11 H11 121.3 . . ?
C10 C11 H11 121.3 . . ?
C11 C12 C13 122.1(3) . . ?
C11 C12 N1 119.5(3) . . ?
C13 C12 N1 118.4(3) . . ?
C12 C13 C8 121.9(3) . . ?
C12 C13 H13 119.0 . . ?
C8 C13 H13 119.0 . . ?
C19 C14 C15 116.3(3) . . ?
C19 C14 C3 120.9(2) . . ?
C15 C14 C3 122.8(2) . . ?
O4 C15 C16 119.8(3) . . ?
O4 C15 C14 118.8(3) . . ?
C16 C15 C14 121.4(3) . . ?
C17 C16 C15 121.1(3) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C18 C17 C16 117.5(3) . . ?
C18 C17 H17 121.2 . . ?
C16 C17 H17 121.2 . . ?
C17 C18 C19 122.4(3) . . ?
C17 C18 N2 119.6(3) . . ?
C19 C18 N2 118.1(3) . . ?
C18 C19 C14 121.3(3) . . ?
C18 C19 H19 119.3 . . ?
C14 C19 H19 119.3 . . ?
O7 C20 C21 110.1(2) . . ?
O7 C20 H20A 109.6 . . ?
C21 C20 H20A 109.6 . . ?
O7 C20 H20B 109.6 . . ?
C21 C20 H20B 109.6 . . ?
H20A C20 H20B 108.2 . . ?
O8 C21 C20 110.7(2) . . ?
O8 C21 H21A 109.5 . . ?
C20 C21 H21A 109.5 . . ?
O8 C21 H21B 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 108.1 . . ?
O3 N1 O2 123.2(3) . . ?
O3 N1 C12 118.9(2) . . ?
O2 N1 C12 117.9(3) . . ?
O5 N2 O6 123.3(3) . . ?
O5 N2 C18 118.2(2) . . ?
O6 N2 C18 118.5(2) . . ?
C9 O1 H1 104(3) . . ?
C9 O1 H1 104(3) . 7_565 ?
H1 O1 H1 21(10) . 7_565 ?
C15 O4 H4 98(4) . . ?
C15 O4 H4 98(4) . 7_565 ?
H4 O4 H4 43(9) . 7_565 ?
C20 O7 C20 109.8(2) . 7_565 ?
C21 O8 C21 110.3(2) 7_565 . ?

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
C8 C1 C2 C3 180.000(1) . . . . ?
C4 C1 C2 C3 59.23(15) . . . . ?
C4 C1 C2 C3 -59.22(15) 7_565 . . . ?
C1 C2 C3 C14 180.000(1) . . . . ?
C1 C2 C3 C6 -58.70(15) . . . . ?
C1 C2 C3 C6 58.70(15) . . . 7_565 ?
C8 C1 C4 C5 -179.14(18) . . . . ?
C2 C1 C4 C5 -58.7(2) . . . . ?
C4 C1 C4 C5 58.3(3) 7_565 . . . ?
C1 C4 C5 C7 -59.2(2) . . . . ?
C1 C4 C5 C6 61.2(2) . . . . ?
C7 C5 C6 C3 59.1(2) . . . . ?
C4 C5 C6 C3 -61.1(2) . . . . ?
C14 C3 C6 C5 178.82(18) . . . . ?
C2 C3 C6 C5 58.1(2) . . . . ?
C6 C3 C6 C5 -58.1(3) 7_565 . . . ?
C4 C5 C7 C5 60.6(3) . . . 7_565 ?
C6 C5 C7 C5 -59.8(3) . . . 7_565 ?
C2 C1 C8 C13 0.000(1) . . . . ?
C4 C1 C8 C13 118.94(16) . . . . ?
C4 C1 C8 C13 -118.94(16) 7_565 . . . ?
C2 C1 C8 C9 180.000(1) . . . . ?
C4 C1 C8 C9 -61.06(16) . . . . ?
C4 C1 C8 C9 61.06(16) 7_565 . . . ?
C13 C8 C9 O1 180.000(1) . . . . ?
C1 C8 C9 O1 0.000(1) . . . . ?
C13 C8 C9 C10 0.000(1) . . . . ?
C1 C8 C9 C10 180.000(1) . . . . ?
O1 C9 C10 C11 180.000(1) . . . . ?
C8 C9 C10 C11 0.000(1) . . . . ?
C9 C10 C11 C12 0.000(1) . . . . ?
C10 C11 C12 C13 0.000(1) . . . . ?
C10 C11 C12 N1 180.000(1) . . . . ?
C11 C12 C13 C8 0.000(1) . . . . ?
N1 C12 C13 C8 180.000(1) . . . . ?
C9 C8 C13 C12 0.000(1) . . . . ?
C1 C8 C13 C12 180.000(1) . . . . ?
C2 C3 C14 C19 0.000(1) . . . . ?
C6 C3 C14 C19 -119.00(16) . . . . ?
C6 C3 C14 C19 119.00(16) 7_565 . . . ?
C2 C3 C14 C15 180.000(1) . . . . ?
C6 C3 C14 C15 61.00(16) . . . . ?
C6 C3 C14 C15 -61.00(16) 7_565 . . . ?
C19 C14 C15 O4 180.000(0) . . . . ?
C3 C14 C15 O4 0.000(1) . . . . ?
C19 C14 C15 C16 0.000(1) . . . . ?
C3 C14 C15 C16 180.000(1) . . . . ?
O4 C15 C16 C17 180.000(0) . . . . ?
C14 C15 C16 C17 0.000(1) . . . . ?
C15 C16 C17 C18 0.000(1) . . . . ?
C16 C17 C18 C19 0.000(1) . . . . ?
C16 C17 C18 N2 180.000(0) . . . . ?
C17 C18 C19 C14 0.000(1) . . . . ?
N2 C18 C19 C14 180.000(1) . . . . ?
C15 C14 C19 C18 0.000(1) . . . . ?
C3 C14 C19 C18 180.000(1) . . . . ?
O7 C20 C21 O8 58.1(3) . . . . ?
C11 C12 N1 O3 180.000(1) . . . . ?
C13 C12 N1 O3 0.000(1) . . . . ?
C11 C12 N1 O2 0.000(1) . . . . ?
C13 C12 N1 O2 180.000(1) . . . . ?
C17 C18 N2 O5 0.000(1) . . . . ?
C19 C18 N2 O5 180.000(0) . . . . ?
C17 C18 N2 O6 180.000(0) . . . . ?
C19 C18 N2 O6 0.000(1) . . . . ?
C21 C20 O7 C20 -59.2(3) . . . 7_565 ?
C20 C21 O8 C21 -56.5(3) . . . 7_565 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O4 H4 O7 0.76(5) 2.05(5) 2.706(3) 145(6) . yes
O1 H1 O8 0.89(5) 1.86(5) 2.715(3) 159(7) 1_556 yes

_refine_diff_density_max         0.780
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.085

####################################################################### 
# 
# 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 2455715'
loop_
_audit_author_name
_audit_author_address
'Masatoshi Kawahata'
;Showa Pharmaceutical University
Japan
;
_audit_update_record             
;
2025-06-02 deposited with the CCDC.	2025-10-13 downloaded from the CCDC.
;

# start vrf
_vrf_PLAT420_2a                  
;
PROBLEM:_D-H Bond Without Acceptor O1--H1A
RESPONSE: The hydrogen atom, H1A was assigned from the
difference Fourier map and refined isotropically.
;
# end vrf

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H22 Br2 O2'
_chemical_formula_weight         478.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   13.123(3)
_cell_length_b                   11.645(2)
_cell_length_c                   12.458(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.293(2)
_cell_angle_gamma                90
_cell_volume                     1827.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6866
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      26.82

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.738
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    4.451
_shelx_estimated_absorpt_T_min   0.349
_shelx_estimated_absorpt_T_max   0.555
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.3349
_exptl_absorpt_correction_T_max  0.4588
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            16373
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.617
_diffrn_reflns_theta_max         26.132
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.925
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             3361
_reflns_number_gt                3174
_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       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2004)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/3 (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)+(0.0158P)²+1.5939P] 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         3361
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0188
_refine_ls_R_factor_gt           0.0173
_refine_ls_wR_factor_ref         0.0430
_refine_ls_wR_factor_gt          0.0425
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.002
_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 0.91624(13) 0.61227(15) 0.89785(14) 0.0133(3) Uani 1 1 d . . . . .
H1 H 0.952579 0.596737 0.978465 0.016 Uiso 1 1 calc R U . . .
C2 C 0.82155(13) 0.53013(14) 0.85791(13) 0.0130(3) Uani 1 1 d . . . . .
H2A H 0.773230 0.538812 0.905783 0.016 Uiso 1 1 calc R U . . .
H2B H 0.847137 0.449762 0.863861 0.016 Uiso 1 1 calc R U . . .
C3 C 0.76120(13) 0.55748(14) 0.73519(13) 0.0108(3) Uani 1 1 d . . . . .
C4 C 0.72771(13) 0.68531(14) 0.72339(14) 0.0101(3) Uani 1 1 d . . . . .
H4A H 0.689555 0.701522 0.644305 0.012 Uiso 1 1 calc R U . . .
H4B H 0.678274 0.700254 0.768959 0.012 Uiso 1 1 calc R U . . .
C5 C 0.82416(13) 0.76684(14) 0.76129(14) 0.0106(3) Uani 1 1 d . . . . .
C6 C 0.87901(13) 0.73814(14) 0.88465(14) 0.0117(3) Uani 1 1 d . . . . .
H6A H 0.940870 0.789452 0.913067 0.014 Uiso 1 1 calc R U . . .
H6B H 0.828891 0.751698 0.929734 0.014 Uiso 1 1 calc R U . . .
C7 C 0.99472(14) 0.59141(15) 0.82902(15) 0.0159(4) Uani 1 1 d . . . . .
H7A H 1.057182 0.642303 0.855453 0.019 Uiso 1 1 calc R U . . .
H7B H 1.019550 0.510759 0.837578 0.019 Uiso 1 1 calc R U . . .
C8 C 0.84003(13) 0.53935(15) 0.66521(14) 0.0138(4) Uani 1 1 d . . . . .
H8A H 0.862638 0.457947 0.670263 0.017 Uiso 1 1 calc R U . . .
H8B H 0.804233 0.556717 0.585773 0.017 Uiso 1 1 calc R U . . .
C9 C 0.93809(13) 0.61659(15) 0.70626(14) 0.0141(4) Uani 1 1 d . . . . .
H9 H 0.987958 0.601459 0.660159 0.017 Uiso 1 1 calc R U . . .
C10 C 0.90419(13) 0.74278(15) 0.69356(14) 0.0130(4) Uani 1 1 d . . . . .
H10A H 0.871035 0.760495 0.613635 0.016 Uiso 1 1 calc R U . . .
H10B H 0.967262 0.792660 0.720826 0.016 Uiso 1 1 calc R U . . .
C11 C 0.66077(13) 0.48395(14) 0.69219(14) 0.0118(3) Uani 1 1 d . . . . .
C12 C 0.64789(14) 0.41502(14) 0.59711(14) 0.0129(3) Uani 1 1 d . . . . .
H12 H 0.704064 0.410646 0.562995 0.015 Uiso 1 1 calc R U . . .
C13 C 0.55563(14) 0.35293(14) 0.55119(14) 0.0138(3) Uani 1 1 d . . . . .
C14 C 0.47173(14) 0.35564(15) 0.59754(15) 0.0159(4) Uani 1 1 d . . . . .
H14 H 0.408725 0.313051 0.565827 0.019 Uiso 1 1 calc R U . . .
C15 C 0.48265(14) 0.42284(15) 0.69219(15) 0.0152(4) Uani 1 1 d . . . . .
H15 H 0.426144 0.425992 0.725917 0.018 Uiso 1 1 calc R U . . .
C16 C 0.57464(14) 0.48563(14) 0.73860(14) 0.0127(3) Uani 1 1 d . . . . .
C17 C 0.78760(13) 0.89249(14) 0.74461(14) 0.0111(3) Uani 1 1 d . . . . .
C18 C 0.72606(13) 0.93414(15) 0.63995(14) 0.0142(4) Uani 1 1 d . . . . .
C19 C 0.69358(15) 1.04839(16) 0.62682(16) 0.0197(4) Uani 1 1 d . . . . .
H19 H 0.650175 1.073736 0.556309 0.024 Uiso 1 1 calc R U . . .
C20 C 0.72331(15) 1.12591(16) 0.71458(16) 0.0195(4) Uani 1 1 d . . . . .
H20 H 0.701005 1.203780 0.705222 0.023 Uiso 1 1 calc R U . . .
C21 C 0.78634(14) 1.08635(15) 0.81597(15) 0.0149(4) Uani 1 1 d . . . . .
C22 C 0.81645(13) 0.97186(14) 0.83115(14) 0.0122(3) Uani 1 1 d . . . . .
H22 H 0.857956 0.947079 0.902727 0.015 Uiso 1 1 calc R U . . .
Br1 Br 0.54667(2) 0.26340(2) 0.42050(2) 0.01602(6) Uani 1 1 d . . . . .
Br2 Br 0.83900(2) 1.19247(2) 0.93494(2) 0.01757(6) Uani 1 1 d . . . . .
O1 O 0.57903(10) 0.55313(11) 0.83194(10) 0.0160(3) Uani 1 1 d . . . . .
H1A H 0.5206(19) 0.5594(19) 0.8355(18) 0.024 Uiso 1 1 d . U . . .
O2 O 0.69962(10) 0.86127(11) 0.55000(10) 0.0169(3) Uani 1 1 d . . . . .
H2 H 0.6685(17) 0.897(2) 0.4937(19) 0.025 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C7 1.533(2) . ?
C1 C2 1.536(2) . ?
C1 C6 1.539(2) . ?
C1 H1 1.0000 . ?
C2 C3 1.545(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C11 1.537(2) . ?
C3 C8 1.543(2) . ?
C3 C4 1.548(2) . ?
C4 C5 1.546(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C17 1.536(2) . ?
C5 C6 1.540(2) . ?
C5 C10 1.546(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C9 1.529(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.535(2) . ?
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 C12 1.401(2) . ?
C11 C16 1.407(2) . ?
C12 C13 1.388(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.380(3) . ?
C13 Br1 1.9091(17) . ?
C14 C15 1.389(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.391(2) . ?
C15 H15 0.9500 . ?
C16 O1 1.391(2) . ?
C17 C22 1.390(2) . ?
C17 C18 1.413(2) . ?
C18 O2 1.370(2) . ?
C18 C19 1.393(3) . ?
C19 C20 1.387(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.380(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.388(2) . ?
C21 Br2 1.9044(18) . ?
C22 H22 0.9500 . ?
O1 H1A 0.78(2) . ?
O2 H2 0.82(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 C1 C2 109.24(14) . . ?
C7 C1 C6 109.51(14) . . ?
C2 C1 C6 110.78(14) . . ?
C7 C1 H1 109.1 . . ?
C2 C1 H1 109.1 . . ?
C6 C1 H1 109.1 . . ?
C1 C2 C3 109.61(14) . . ?
C1 C2 H2A 109.7 . . ?
C3 C2 H2A 109.7 . . ?
C1 C2 H2B 109.7 . . ?
C3 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C11 C3 C8 111.85(13) . . ?
C11 C3 C2 112.43(13) . . ?
C8 C3 C2 106.99(13) . . ?
C11 C3 C4 108.06(13) . . ?
C8 C3 C4 107.19(13) . . ?
C2 C3 C4 110.21(13) . . ?
C5 C4 C3 112.04(13) . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C17 C5 C6 112.49(13) . . ?
C17 C5 C10 109.45(13) . . ?
C6 C5 C10 107.85(13) . . ?
C17 C5 C4 110.23(13) . . ?
C6 C5 C4 106.55(13) . . ?
C10 C5 C4 110.20(13) . . ?
C1 C6 C5 111.02(13) . . ?
C1 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
C1 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C9 C7 C1 108.34(14) . . ?
C9 C7 H7A 110.0 . . ?
C1 C7 H7A 110.0 . . ?
C9 C7 H7B 110.0 . . ?
C1 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
C9 C8 C3 111.33(14) . . ?
C9 C8 H8A 109.4 . . ?
C3 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C3 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C7 C9 C10 109.45(14) . . ?
C7 C9 C8 110.33(14) . . ?
C10 C9 C8 109.62(14) . . ?
C7 C9 H9 109.1 . . ?
C10 C9 H9 109.1 . . ?
C8 C9 H9 109.1 . . ?
C9 C10 C5 109.86(14) . . ?
C9 C10 H10A 109.7 . . ?
C5 C10 H10A 109.7 . . ?
C9 C10 H10B 109.7 . . ?
C5 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
C12 C11 C16 115.79(15) . . ?
C12 C11 C3 120.15(15) . . ?
C16 C11 C3 123.95(15) . . ?
C13 C12 C11 122.08(16) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C14 C13 C12 121.45(16) . . ?
C14 C13 Br1 120.26(13) . . ?
C12 C13 Br1 118.29(13) . . ?
C13 C14 C15 117.64(16) . . ?
C13 C14 H14 121.2 . . ?
C15 C14 H14 121.2 . . ?
C14 C15 C16 121.33(16) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C15 C16 O1 118.17(15) . . ?
C15 C16 C11 121.71(16) . . ?
O1 C16 C11 120.11(15) . . ?
C22 C17 C18 116.64(15) . . ?
C22 C17 C5 121.47(15) . . ?
C18 C17 C5 121.86(15) . . ?
O2 C18 C19 119.78(15) . . ?
O2 C18 C17 119.34(15) . . ?
C19 C18 C17 120.87(16) . . ?
C20 C19 C18 121.35(17) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C21 C20 C19 117.90(17) . . ?
C21 C20 H20 121.1 . . ?
C19 C20 H20 121.1 . . ?
C20 C21 C22 121.31(17) . . ?
C20 C21 Br2 119.27(14) . . ?
C22 C21 Br2 119.33(13) . . ?
C21 C22 C17 121.86(16) . . ?
C21 C22 H22 119.1 . . ?
C17 C22 H22 119.1 . . ?
C16 O1 H1A 106.8(17) . . ?
C18 O2 H2 109.8(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
C7 C1 C2 C3 -63.77(17) . . . . ?
C6 C1 C2 C3 56.95(18) . . . . ?
C1 C2 C3 C11 -176.03(13) . . . . ?
C1 C2 C3 C8 60.80(17) . . . . ?
C1 C2 C3 C4 -55.41(18) . . . . ?
C11 C3 C4 C5 -178.23(13) . . . . ?
C8 C3 C4 C5 -57.53(17) . . . . ?
C2 C3 C4 C5 58.56(18) . . . . ?
C3 C4 C5 C17 178.19(13) . . . . ?
C3 C4 C5 C6 -59.47(17) . . . . ?
C3 C4 C5 C10 57.27(17) . . . . ?
C7 C1 C6 C5 59.66(18) . . . . ?
C2 C1 C6 C5 -60.89(18) . . . . ?
C17 C5 C6 C1 -179.01(13) . . . . ?
C10 C5 C6 C1 -58.21(18) . . . . ?
C4 C5 C6 C1 60.09(17) . . . . ?
C2 C1 C7 C9 61.32(18) . . . . ?
C6 C1 C7 C9 -60.17(18) . . . . ?
C11 C3 C8 C9 177.87(13) . . . . ?
C2 C3 C8 C9 -58.60(18) . . . . ?
C4 C3 C8 C9 59.61(17) . . . . ?
C1 C7 C9 C10 61.98(18) . . . . ?
C1 C7 C9 C8 -58.73(18) . . . . ?
C3 C8 C9 C7 58.96(18) . . . . ?
C3 C8 C9 C10 -61.65(18) . . . . ?
C7 C9 C10 C5 -62.45(17) . . . . ?
C8 C9 C10 C5 58.69(18) . . . . ?
C17 C5 C10 C9 -177.98(13) . . . . ?
C6 C5 C10 C9 59.34(17) . . . . ?
C4 C5 C10 C9 -56.60(17) . . . . ?
C8 C3 C11 C12 -2.5(2) . . . . ?
C2 C3 C11 C12 -122.85(16) . . . . ?
C4 C3 C11 C12 115.30(16) . . . . ?
C8 C3 C11 C16 -178.36(15) . . . . ?
C2 C3 C11 C16 61.2(2) . . . . ?
C4 C3 C11 C16 -60.6(2) . . . . ?
C16 C11 C12 C13 0.4(2) . . . . ?
C3 C11 C12 C13 -175.82(15) . . . . ?
C11 C12 C13 C14 -0.3(3) . . . . ?
C11 C12 C13 Br1 179.30(13) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
Br1 C13 C14 C15 -179.62(12) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C14 C15 C16 O1 178.55(15) . . . . ?
C14 C15 C16 C11 -0.1(3) . . . . ?
C12 C11 C16 C15 -0.2(2) . . . . ?
C3 C11 C16 C15 175.86(15) . . . . ?
C12 C11 C16 O1 -178.84(14) . . . . ?
C3 C11 C16 O1 -2.8(2) . . . . ?
C6 C5 C17 C22 8.6(2) . . . . ?
C10 C5 C17 C22 -111.22(17) . . . . ?
C4 C5 C17 C22 127.42(16) . . . . ?
C6 C5 C17 C18 -173.47(15) . . . . ?
C10 C5 C17 C18 66.7(2) . . . . ?
C4 C5 C17 C18 -54.7(2) . . . . ?
C22 C17 C18 O2 176.78(15) . . . . ?
C5 C17 C18 O2 -1.2(2) . . . . ?
C22 C17 C18 C19 -2.2(2) . . . . ?
C5 C17 C18 C19 179.85(16) . . . . ?
O2 C18 C19 C20 -176.76(16) . . . . ?
C17 C18 C19 C20 2.2(3) . . . . ?
C18 C19 C20 C21 0.0(3) . . . . ?
C19 C20 C21 C22 -2.0(3) . . . . ?
C19 C20 C21 Br2 174.68(14) . . . . ?
C20 C21 C22 C17 2.0(3) . . . . ?
Br2 C21 C22 C17 -174.68(12) . . . . ?
C18 C17 C22 C21 0.1(2) . . . . ?
C5 C17 C22 C21 178.10(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O1 0.82(2) 2.11(2) 2.9095(18) 166(2) 4_575 yes

_refine_diff_density_max         0.382
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.055

